data_ban1308 
_audit_creation_date        "13-03-08"
_audit_creation_method CRYSTALS_ver_14.40
_audit_update_record                   
;
2013-03-12 - Report on C23 H24 N4 O12
            by Anthony C. Willis
            for  Ping Lan and Martin Banwell

2013-03-12 - racemic

2013-03-12 - passes checkcif tests

;

_oxford_structure_analysis_title  'ban1308 At 15:18 on 8/ 3'
_chemical_name_systematic         ?
_chemical_melting_point           ?

_cell_length_a                    8.6279(1)
_cell_length_b                    26.7808(5)
_cell_length_c                    9.8839(2)
_cell_angle_alpha                 90
_cell_angle_beta                  110.4722(10)
_cell_angle_gamma                 90
_cell_volume                      2139.55(7)
 
_symmetry_cell_setting            'monoclinic' 
_symmetry_space_group_name_H-M    'P 1 21/a 1 ' 
_symmetry_space_group_name_Hall   ? 
loop_
 _symmetry_equiv_pos_as_xyz
 'x,y,z'
 '-x,-y,-z'
 '-x+1/2,y+1/2,-z'
 'x+1/2,-y+1/2,z'

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source  
 C       0.0033   0.0016   2.3100  20.8439   1.0200  10.2075   1.5886   0.5687
   0.8650  51.6512   0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
 H       0.0000   0.0000   0.4930  10.5109   0.3229  26.1257   0.1402   3.1424
   0.0408  57.7998   0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
 N       0.0061   0.0033  12.2126   0.0057   3.1322   9.8933   2.0125  28.9975
   1.1663   0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
 O       0.0106   0.0060   3.0485  13.2771   2.2868   5.7011   1.5463   0.3239
   0.8670  32.9089   0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
 
 
_cell_formula_units_Z                    4

# Given Formula = C22 H20 N4 O11 
# Dc =      1.60 Fooo =   1072.00 Mu =      1.31 M =    516.42
# Found Formula = C22 H20 N4 O11 
# Dc =      1.60 FOOO =   1072.00 Mu =      1.31 M =    516.42

_chemical_formula_sum             'C22 H20 N4 O11'
_chemical_formula_moiety          ' C16 H18 N O4 +, C6 H2 N3 O7 -'
_chemical_compound_source                local
_chemical_formula_weight            516.42
 
 
_cell_measurement_reflns_used        27329
_cell_measurement_theta_min              3
_cell_measurement_theta_max             27.5
_cell_measurement_temperature          200
 
_exptl_crystal_description        'prism' 
_exptl_crystal_colour             'yellow' 
_exptl_crystal_size_min           0.160 
_exptl_crystal_size_mid           0.160 
_exptl_crystal_size_max           0.430 
 
_exptl_crystal_density_diffrn     1.603 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     'not measured' 
# Non-dispersive F(000): 
_exptl_crystal_F_000              1072 
_exptl_absorpt_coefficient_mu     0.131 
 
# Sheldrick geometric approximatio 0.98 0.98 
# Absorption correction 

loop_
_exptl_crystal_face_index_h 
_exptl_crystal_face_index_k 
_exptl_crystal_face_index_l 
_exptl_crystal_face_perp_dist 
    1    0    0  0.220
   -1    0    0  0.280
    0    1    0  0.020
    0   -1    0  0.030
    0    0    1  0.100
    0    0   -1  0.120


_exptl_absorpt_correction_type 'integration' 
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;

# For a Kappa CCD, set Tmin to 1.0 and 
# Tmax to the ratio of max:min frame scales in scale_all.log 
_diffrn_measurement_device_type   'Nonius KappaCCD' 
_diffrn_measurement_device        'Area' 
_diffrn_radiation_monochromator   'graphite' 
_diffrn_radiation_type            'Mo K\a'
_diffrn_radiation_wavelength           0.71073
_diffrn_measurement_method ' φ and ω scans with CCD ' 
_diffrn_special_details
;
CCD data collecting conditions-
phi and omega scans of width 1.1 deg at rate 22 sec/frame,
crystal-detector distance 45mm,
multiple scan sets so over 90 percent of data collected with 4-fold  
redundancy or more.
;
 
# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection        'COLLECT (Nonius, 2001).' 
_computing_cell_refinement        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' 
_computing_data_reduction         'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' 
_computing_structure_solution     'SIR92 (Altomare et al., 1994)' 
_computing_structure_refinement   'CRYSTALS (Betteridge et al., 2003)' 
_computing_publication_material   'CRYSTALS (Betteridge et al., 2003)' 
_computing_molecular_graphics 
; 
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
; 
 
_diffrn_standards_interval_time   . 
_diffrn_standards_interval_count  . 
_diffrn_standards_number          0 
_diffrn_standards_decay_%         ? 
 
_diffrn_ambient_temperature        200
_diffrn_reflns_number             35395 
_reflns_number_total              4899 
_diffrn_reflns_av_R_equivalents   0.058 
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 4899 
# Theoretical number of reflections is about 9813 
 
 
_diffrn_reflns_theta_min          2.632 
_diffrn_reflns_theta_max          27.482 
_diffrn_measured_fraction_theta_max 0.998 
 
_diffrn_reflns_theta_full         27.482 
_diffrn_measured_fraction_theta_full 0.998 
 
 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -34 
_diffrn_reflns_limit_k_max        33 
_diffrn_reflns_limit_l_min        -12 
_diffrn_reflns_limit_l_max        12 
_reflns_limit_h_min               -11 
_reflns_limit_h_max               10 
_reflns_limit_k_min               0 
_reflns_limit_k_max               34 
_reflns_limit_l_min               0 
_reflns_limit_l_max               12 
 
_oxford_diffrn_Wilson_B_factor    2.57 
_oxford_diffrn_Wilson_scale       8.14 
 
_atom_sites_solution_primary      direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens    difmap
 
_refine_diff_density_min          -0.52 
_refine_diff_density_max          0.49 
 
 
# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 
 
 
# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref     I>-10.0\s(I)
_refine_ls_number_reflns          4899 
_refine_ls_number_restraints      0 
_refine_ls_number_parameters      394 
_oxford_refine_ls_R_factor_ref    0.0749 
_refine_ls_wR_factor_ref          0.1052 
_refine_ls_goodness_of_fit_ref    0.9482 
_refine_ls_shift/su_max           0.0054572 
_refine_ls_shift/su_mean          0.0004352 
 
 
# The values computed with all filters except I/sigma 
_oxford_reflns_number_all         4899 
_refine_ls_R_factor_all           0.0749 
_refine_ls_wR_factor_all          0.1052 
 
# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression      I>2.0σ(I)
_reflns_number_gt                 3417 
_refine_ls_R_factor_gt            0.0438 
_refine_ls_wR_factor_gt           0.0938 
 
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration  '.' 
 
 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full
_refine_ls_hydrogen_treatment     refxyz         #undef, noref, refall,
                                                 # refxyz, refU, constr or mixed
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.05P)² + 1.03P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# 1. SUBMISSION DETAILS                                                       
_publ_requested_journal               ' test '
_publ_requested_category              FO 
_publ_contact_author_name             ' Anthony C. Willis '

_publ_contact_author_address
;
Research School of Chemistry,
Australian National University,
Canberra, A. C. T. 0200, Australia
;
_publ_contact_letter
;
    ENTER TEXT OF LETTER
;

_publ_requested_coeditor_name          ?
_publ_contact_author_phone            ' 61 2 6125 4109 '
_publ_contact_author_fax              ' 61 2 6125 0750 '
_publ_contact_author_email            ' willis@rsc.anu.edu.au '
                                                                                
#=============================================================================  
# 2. PROCESSING SUMMARY (IUCr Office Use Only)                                  
_journal_date_recd_electronic     ?                                             
_journal_date_to_coeditor         ?                                             
_journal_date_from_coeditor       ?                                             
_journal_date_accepted            ?                                             
_journal_date_printers_first      ?                                             
_journal_date_printers_final      ?                                             
_journal_date_proofs_out          ?                                             
_journal_date_proofs_in           ?                                             
_journal_coeditor_name            ?                                             
_journal_coeditor_code            ?                                             
_journal_coeditor_notes                                                         
;                                                                               
                                  ?                                             
;                                                                               
_journal_techeditor_code          ?                                             
_journal_techeditor_notes                                                       
;                                                                               
                                  ?                                             
;                                                                               
_journal_coden_ASTM               ?                                             
_journal_name_full                ?                                             
_journal_year                     ?                                             
_journal_volume                   ?                                             
_journal_issue                    ?                                             
_journal_page_first               ?                                             
_journal_page_last                ?                                             
_journal_suppl_publ_number        ?                                             
_journal_suppl_publ_pages         ?                                             
#=============================================================================  
# 3. TITLE AND AUTHOR LIST                                                      
_publ_section_title                                                             
;
Crystal structure of C₁₆H₁₈NO₄⁺C₆H₂N₃O₇⁻⁻
 --- ban1308
;                                                                               
# The loop structure below should contain the names and addresses of all        
# authors, in the required order of publication. Repeat as necessary.           
loop_
_publ_author_name
_publ_author_address
' Ping Lan '
;
Research School of Chemistry,
The Australian National University,
Canberra, A. C. T. 0200, Australia
;
'  Martin G. Banwell '
;
Research School of Chemistry,
The Australian National University,
Canberra, A. C. T. 0200, Australia
;
'  Anthony C. Willis '
;
Research School of Chemistry,
The Australian National University,
Canberra, A. C. T. 0200, Australia
;
#============================================================================== 
# 4. TEXT                                                                       
_publ_section_abstract  #Text of the abstract                                   
;
The crystal structure of C₁₆H₁₈NO₄⁺C₆H₂N₃O₇⁻⁻
 is reported.
 
;                                                                               
_publ_section_comment  #Text of the paper                                       
;
 

The crystallographic asymmetric unit consists of 
one C₁₆H₁₈NO₄⁺ cation and 
one C₆H₂N₃O₇⁻⁻ anion.

;                                                                               
_publ_section_acknowledgements  # Acknowledgments                               
;

;                                                                               
_publ_section_figure_captions  #Captions to figures                             
;

;                                                                               
_publ_section_exptl_refinement                                                  
# see also _refine_ls_hydrogen for refinement keywords.                         
;                                                                               
The crystal is racemic.


;                                                                               
_refine_special_details
;



The H atoms were all located in a difference map, but those 
attached to carbon atoms of the cation and anion 
were repositioned geometrically. 
The H atoms were initially refined with soft restraints on the 
bond lengths and angles to regularise their geometry 
(C---H in the range 0.93--0.98, N---H = 0.86,
O---H = 0.82 Å) and with
Uiso(H) in the range 1.2-1.5 times Ueq of the parent atom, 
after which the positions were refined without restraints
and the displacement parameters were held fixed. 



The largest peaks in the final difference electron density map are 
located midway between bonded atoms or adjacent to O
atoms of nitro groups of the anion.
;                                                                               
_publ_section_exptl_prep                                                        
;
The compound was prepared by PL and crystallized from 
methanol.
The sample ID is LPE20E1CHUP.
;                                                                               



# Insert your own references if required - in alphabetical order 
_publ_section_references 
;
Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M. C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435--?.

Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J.
(2003). J. Appl. Cryst. 36, 1487--?.

Nonius (1997--2001). COLLECT. Nonius BV, Delft, The Netherlands.

Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic
Press.

Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K.
(2000). maXus  Computer Program for the Solution and Refinement of
Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The
University of Glasgow.

Coppens, P. (1970).  The Evaluation of Absorption and Extinction in
Single-Crystal Structure Analysis.  Crystallographic Computing.  F. R. Ahmed,
S. R. Hall and C. P. Huber, eds., Munksgaard. Copenhagen. pp 255-270.

Molecular Structure Corporation. (1992--1997). TEXSAN. Single Crystal
Structure Analysis Software. Version 1.8. MSC, 3200 Research Forest Drive, The
Woodlands, TX 77381, USA.

Johnson, C. K. (1976). ORTEPII, A Fortran Thermal-Ellipsoid Plot
Program, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge,
Tennessee, USA.


; 

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C 0.4191(2) 0.59770(7) 0.19450(18) 0.0268 1.0000 Uani . . . . . . 
C2 C 0.5069(2) 0.61837(7) 0.12294(19) 0.0295 1.0000 Uani . . . . . . 
C3 C 0.4979(2) 0.67256(7) 0.08213(19) 0.0300 1.0000 Uani . . . . . . 
O4 O 0.64415(14) 0.69852(4) 0.17333(14) 0.0302 1.0000 Uani . . . . . . 
C5 C 0.3411(2) 0.69706(7) 0.0887(2) 0.0301 1.0000 Uani . . . . . . 
C6 C 0.3180(2) 0.68225(6) 0.22840(19) 0.0253 1.0000 Uani . . . . . . 
N7 N 0.15701(17) 0.70121(6) 0.23619(15) 0.0275 1.0000 Uani . . . . . . 
C8 C 0.0265(2) 0.66771(7) 0.1357(2) 0.0309 1.0000 Uani . . . . . . 
C9 C 0.1102(2) 0.61723(7) 0.13743(18) 0.0295 1.0000 Uani . . . . . . 
O10 O 0.09315(16) 0.60637(6) -0.00708(14) 0.0434 1.0000 Uani . . . . . . 
C11 C 0.29522(19) 0.62618(6) 0.24045(17) 0.0240 1.0000 Uani . . . . . . 
C12 C 0.1623(2) 0.69899(7) 0.3893(2) 0.0310 1.0000 Uani . . . . . . 
C13 C 0.2321(2) 0.65011(6) 0.46084(18) 0.0275 1.0000 Uani . . . . . . 
C14 C 0.2239(2) 0.64130(7) 0.59879(19) 0.0334 1.0000 Uani . . . . . . 
C15 C 0.2826(2) 0.59658(7) 0.66187(19) 0.0344 1.0000 Uani . . . . . . 
O16 O 0.28942(19) 0.57913(6) 0.79468(14) 0.0527 1.0000 Uani . . . . . . 
C17 C 0.3361(3) 0.52768(9) 0.7978(2) 0.0489 1.0000 Uani . . . . . . 
O18 O 0.40213(17) 0.52046(5) 0.68433(14) 0.0448 1.0000 Uani . . . . . . 
C19 C 0.3493(2) 0.56139(7) 0.59514(19) 0.0311 1.0000 Uani . . . . . . 
C20 C 0.3605(2) 0.56926(6) 0.46268(18) 0.0277 1.0000 Uani . . . . . . 
C21 C 0.30008(19) 0.61485(6) 0.39346(17) 0.0250 1.0000 Uani . . . . . . 
C22 C 0.7465(2) 0.64938(7) 0.54613(19) 0.0315 1.0000 Uani . . . . . . 
C23 C 0.8096(2) 0.59936(7) 0.54201(18) 0.0294 1.0000 Uani . . . . . . 
C24 C 0.8210(2) 0.56321(7) 0.64421(19) 0.0301 1.0000 Uani . . . . . . 
C25 C 0.7713(2) 0.57412(7) 0.75921(18) 0.0299 1.0000 Uani . . . . . . 
C26 C 0.7140(2) 0.62119(7) 0.77611(19) 0.0321 1.0000 Uani . . . . . . 
C27 C 0.7008(2) 0.65662(7) 0.67326(19) 0.0324 1.0000 Uani . . . . . . 
O28 O 0.73581(19) 0.68329(5) 0.45665(14) 0.0445 1.0000 Uani . . . . . . 
N29 N 0.86897(18) 0.58506(6) 0.42643(16) 0.0348 1.0000 Uani . . . . . . 
O30 O 0.85414(18) 0.61413(6) 0.32795(16) 0.0537 1.0000 Uani . . . . . . 
O31 O 0.9365(2) 0.54453(6) 0.43345(18) 0.0656 1.0000 Uani . . . . . . 
N32 N 0.78467(19) 0.53667(6) 0.86740(16) 0.0347 1.0000 Uani . . . . . . 
O33 O 0.84224(19) 0.49564(5) 0.85500(15) 0.0465 1.0000 Uani . . . . . . 
O34 O 0.73841(19) 0.54685(6) 0.96832(15) 0.0502 1.0000 Uani . . . . . . 
N35 N 0.6400(2) 0.70549(6) 0.69745(18) 0.0428 1.0000 Uani . . . . . . 
O36 O 0.6781(3) 0.71990(7) 0.82266(18) 0.0830 1.0000 Uani . . . . . . 
O37 O 0.55116(19) 0.72960(5) 0.59456(16) 0.0512 1.0000 Uani . . . . . . 
H11 H 0.432(2) 0.5616(7) 0.2195(19) 0.0323 1.0000 Uiso . . . . . . 
H21 H 0.588(2) 0.5974(7) 0.098(2) 0.0354 1.0000 Uiso . . . . . . 
H31 H 0.498(2) 0.6769(7) -0.018(2) 0.0344 1.0000 Uiso . . . . . . 
H51 H 0.344(2) 0.7343(8) 0.081(2) 0.0358 1.0000 Uiso . . . . . . 
H52 H 0.246(2) 0.6844(7) 0.005(2) 0.0361 1.0000 Uiso . . . . . . 
H61 H 0.409(2) 0.6951(6) 0.314(2) 0.0281 1.0000 Uiso . . . . . . 
H71 H 0.142(2) 0.7344(8) 0.208(2) 0.0400 1.0000 Uiso . . . . . . 
H81 H -0.009(2) 0.6819(7) 0.037(2) 0.0360 1.0000 Uiso . . . . . . 
H82 H -0.063(2) 0.6660(7) 0.169(2) 0.0356 1.0000 Uiso . . . . . . 
H91 H 0.056(2) 0.5893(7) 0.1773(19) 0.0334 1.0000 Uiso . . . . . . 
H101 H 0.135(3) 0.5758(10) -0.004(3) 0.0666 1.0000 Uiso . . . . . . 
H121 H 0.229(2) 0.7264(7) 0.439(2) 0.0362 1.0000 Uiso . . . . . . 
H122 H 0.047(2) 0.7030(7) 0.386(2) 0.0360 1.0000 Uiso . . . . . . 
H141 H 0.177(2) 0.6669(7) 0.646(2) 0.0397 1.0000 Uiso . . . . . . 
H171 H 0.430(3) 0.5205(8) 0.893(3) 0.0585 1.0000 Uiso . . . . . . 
H172 H 0.233(3) 0.5067(9) 0.775(2) 0.0594 1.0000 Uiso . . . . . . 
H201 H 0.410(2) 0.5439(7) 0.4161(19) 0.0324 1.0000 Uiso . . . . . . 
H241 H 0.862(2) 0.5309(7) 0.634(2) 0.0358 1.0000 Uiso . . . . . . 
H261 H 0.683(2) 0.6277(7) 0.857(2) 0.0374 1.0000 Uiso . . . . . . 
H401 H 0.676(3) 0.6856(8) 0.265(2) 0.0456 1.0000 Uiso . . . . . . 


_refine_ls_extinction_method 
    'None'
_oxford_refine_ls_scale 0.3827(5) 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_site_symmetry_1
 _geom_bond_atom_site_label_2
 _geom_bond_site_symmetry_2
 _geom_bond_distance
 _geom_bond_publ_flag
C1 . C2 . 1.325(2)    yes
C1 . C11 . 1.507(2)    yes
C1 . H11 . 0.994(19)    no
C2 . C3 . 1.501(3)    yes
C2 . H21 . 0.992(19)    no
C3 . O4 . 1.446(2)    yes
C3 . C5 . 1.525(2)    yes
C3 . H31 . 1.00(2)    no
O4 . H401 . 0.92(2)    no
C5 . C6 . 1.516(2)    yes
C5 . H51 . 1.00(2)    no
C5 . H52 . 1.00(2)    no
C6 . N7 . 1.506(2)    yes
C6 . C11 . 1.524(2)    yes
C6 . H61 . 0.994(18)    no
N7 . C8 . 1.509(2)    yes
N7 . C12 . 1.499(2)    yes
N7 . H71 . 0.93(2)    no
C8 . C9 . 1.530(3)    yes
C8 . H81 . 0.99(2)    no
C8 . H82 . 0.94(2)    no
C9 . O10 . 1.414(2)    yes
C9 . C11 . 1.583(2)    yes
C9 . H91 . 1.028(19)    no
O10 . H101 . 0.89(3)    no
C11 . C21 . 1.529(2)    yes
C12 . C13 . 1.510(2)    yes
C12 . H121 . 0.96(2)    no
C12 . H122 . 0.992(19)    no
C13 . C14 . 1.409(2)    yes
C13 . C21 . 1.397(2)    yes
C14 . C15 . 1.363(3)    yes
C14 . H141 . 0.99(2)    no
C15 . O16 . 1.375(2)    yes
C15 . C19 . 1.385(3)    yes
O16 . C17 . 1.433(3)    yes
C17 . O18 . 1.437(2)    yes
C17 . H171 . 1.02(2)    no
C17 . H172 . 1.01(2)    no
O18 . C19 . 1.381(2)    yes
C19 . C20 . 1.362(2)    yes
C20 . C21 . 1.407(2)    yes
C20 . H201 . 0.995(19)    no
C22 . C23 . 1.452(3)    yes
C22 . C27 . 1.456(3)    yes
C22 . O28 . 1.248(2)    yes
C23 . C24 . 1.378(2)    yes
C23 . N29 . 1.457(2)    yes
C24 . C25 . 1.379(3)    yes
C24 . H241 . 0.95(2)    no
C25 . C26 . 1.385(3)    yes
C25 . N32 . 1.441(2)    yes
C26 . C27 . 1.366(2)    yes
C26 . H261 . 0.94(2)    no
C27 . N35 . 1.461(2)    yes
N29 . O30 . 1.218(2)    yes
N29 . O31 . 1.223(2)    yes
N32 . O33 . 1.229(2)    yes
N32 . O34 . 1.228(2)    yes
N35 . O36 . 1.226(2)    yes
N35 . O37 . 1.222(2)    yes
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_site_symmetry_1
 _geom_angle_atom_site_label_2
 _geom_angle_site_symmetry_2
 _geom_angle_atom_site_label_3
 _geom_angle_site_symmetry_3
 _geom_angle
 _geom_angle_publ_flag
C2 . C1 . C11 . 123.21(16)    yes
C2 . C1 . H11 . 120.3(11)    no
C11 . C1 . H11 . 116.5(11)    no
C1 . C2 . C3 . 124.19(16)    yes
C1 . C2 . H21 . 118.8(11)    no
C3 . C2 . H21 . 117.0(11)    no
C2 . C3 . O4 . 110.22(14)    yes
C2 . C3 . C5 . 111.57(14)    yes
O4 . C3 . C5 . 111.10(14)    yes
C2 . C3 . H31 . 111.2(10)    no
O4 . C3 . H31 . 104.9(11)    no
C5 . C3 . H31 . 107.7(11)    no
C3 . O4 . H401 . 109.3(13)    no
C3 . C5 . C6 . 109.11(14)    yes
C3 . C5 . H51 . 112.0(11)    no
C6 . C5 . H51 . 110.4(11)    no
C3 . C5 . H52 . 107.5(11)    no
C6 . C5 . H52 . 109.8(11)    no
H51 . C5 . H52 . 108.0(15)    no
C5 . C6 . N7 . 112.09(13)    yes
C5 . C6 . C11 . 112.99(14)    yes
N7 . C6 . C11 . 100.46(12)    yes
C5 . C6 . H61 . 111.7(10)    no
N7 . C6 . H61 . 108.0(10)    no
C11 . C6 . H61 . 111.0(10)    no
C6 . N7 . C8 . 104.80(13)    yes
C6 . N7 . C12 . 109.60(13)    yes
C8 . N7 . C12 . 113.15(14)    yes
C6 . N7 . H71 . 110.2(12)    no
C8 . N7 . H71 . 112.4(12)    no
C12 . N7 . H71 . 106.7(12)    no
N7 . C8 . C9 . 106.08(13)    yes
N7 . C8 . H81 . 108.7(11)    no
C9 . C8 . H81 . 109.4(11)    no
N7 . C8 . H82 . 108.2(12)    no
C9 . C8 . H82 . 113.3(12)    no
H81 . C8 . H82 . 111.0(16)    no
C8 . C9 . O10 . 106.77(15)    yes
C8 . C9 . C11 . 103.85(13)    yes
O10 . C9 . C11 . 113.98(13)    yes
C8 . C9 . H91 . 111.8(10)    no
O10 . C9 . H91 . 109.7(10)    no
C11 . C9 . H91 . 110.6(10)    no
C9 . O10 . H101 . 104.7(16)    no
C6 . C11 . C1 . 110.53(13)    yes
C6 . C11 . C9 . 103.15(13)    yes
C1 . C11 . C9 . 113.04(13)    yes
C6 . C11 . C21 . 108.25(13)    yes
C1 . C11 . C21 . 114.88(13)    yes
C9 . C11 . C21 . 106.20(13)    yes
N7 . C12 . C13 . 111.92(14)    yes
N7 . C12 . H121 . 106.7(11)    no
C13 . C12 . H121 . 110.8(11)    no
N7 . C12 . H122 . 106.6(11)    no
C13 . C12 . H122 . 110.0(11)    no
H121 . C12 . H122 . 110.7(16)    no
C12 . C13 . C14 . 116.84(15)    yes
C12 . C13 . C21 . 121.87(15)    yes
C14 . C13 . C21 . 121.28(16)    yes
C13 . C14 . C15 . 116.95(16)    yes
C13 . C14 . H141 . 120.2(11)    no
C15 . C14 . H141 . 122.8(11)    no
C14 . C15 . O16 . 128.33(17)    yes
C14 . C15 . C19 . 121.97(16)    yes
O16 . C15 . C19 . 109.70(16)    yes
C15 . O16 . C17 . 105.36(15)    yes
O16 . C17 . O18 . 107.35(16)    yes
O16 . C17 . H171 . 109.2(13)    no
O18 . C17 . H171 . 106.6(13)    no
O16 . C17 . H172 . 108.0(13)    no
O18 . C17 . H172 . 108.4(13)    no
H171 . C17 . H172 . 116.9(18)    no
C17 . O18 . C19 . 105.00(14)    yes
C15 . C19 . O18 . 109.61(15)    yes
C15 . C19 . C20 . 122.21(16)    yes
O18 . C19 . C20 . 128.16(16)    yes
C19 . C20 . C21 . 117.56(16)    yes
C19 . C20 . H201 . 121.6(11)    no
C21 . C20 . H201 . 120.8(10)    no
C11 . C21 . C20 . 122.05(14)    yes
C11 . C21 . C13 . 117.81(14)    yes
C20 . C21 . C13 . 120.01(15)    yes
C23 . C22 . C27 . 111.38(15)    yes
C23 . C22 . O28 . 125.94(17)    yes
C27 . C22 . O28 . 122.65(17)    yes
C22 . C23 . C24 . 123.99(16)    yes
C22 . C23 . N29 . 120.16(15)    yes
C24 . C23 . N29 . 115.83(16)    yes
C23 . C24 . C25 . 119.50(17)    yes
C23 . C24 . H241 . 119.5(11)    no
C25 . C24 . H241 . 121.0(11)    no
C24 . C25 . C26 . 121.28(16)    yes
C24 . C25 . N32 . 119.78(16)    yes
C26 . C25 . N32 . 118.89(16)    yes
C25 . C26 . C27 . 118.86(17)    yes
C25 . C26 . H261 . 119.2(12)    no
C27 . C26 . H261 . 122.0(12)    no
C22 . C27 . C26 . 124.94(17)    yes
C22 . C27 . N35 . 118.82(15)    yes
C26 . C27 . N35 . 116.22(16)    yes
C23 . N29 . O30 . 119.42(16)    yes
C23 . N29 . O31 . 118.70(15)    yes
O30 . N29 . O31 . 121.85(16)    yes
C25 . N32 . O33 . 118.58(15)    yes
C25 . N32 . O34 . 118.94(16)    yes
O33 . N32 . O34 . 122.48(16)    yes
C27 . N35 . O36 . 117.54(16)    yes
C27 . N35 . O37 . 119.60(16)    yes
O36 . N35 . O37 . 122.84(17)    yes
loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_site_symmetry_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_site_symmetry_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_site_symmetry_A
 _geom_hbond_angle_DHA
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_publ_flag
O4  . H401 . O28 .     159.7(19) 0.92(2) 1.78(2) 2.662(3)    yes
O4  . H401 . O30 .     120.3(16) 0.92(2) 2.40(2) 2.965(3)    yes
N7  . H71  . O4  4_465 171.3(18) 0.93(2) 1.83(2) 2.750(3)    yes
O10 . H101 . O33 2_666 135(2)    0.89(3) 2.38(2) 3.074(3)    yes

#------------------------------------------------------------------------------
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
 O4        O28       2.662(2)   . . no
 O4        N7        2.750(2)   . 4_565 no
 O4        O30       2.965(2)   . . no
 O4        C12       3.447(2)   . 4_565 no
 O4        C6        3.489(2)   . 4_565 no
 O4        C5        3.522(2)   . 4_565 no
 O4        C8        3.544(2)   . 1_655 no
 O10       C25       3.051(2)   . 1_454 no
 O10       O33       3.074(2)   . 2_666 no
 O10       O16       3.092(2)   . 1_554 no
 O10       N32       3.130(2)   . 1_454 no
 O10       C26       3.248(2)   . 1_454 no
 O10       O34       3.383(2)   . 1_454 no
 O16       C2        3.300(2)   . 1_556 no
 O18       N32       3.190(2)   . . no
 O18       O31       3.247(2)   . 2_666 no
 O18       O34       3.332(2)   . . no
 O18       C25       3.333(2)   . . no
 O18       C1        3.540(2)   . 2_666 no
 O18       N29       3.587(2)   . 2_666 no
 O28       C12       3.239(2)   . 4_565 no
 O28       O37       3.480(2)   . 4_565 no
 O28       C6        3.521(2)   . . no
 O28       C3        3.561(2)   . . no
 O30       C2        2.975(2)   . . no
 O30       C8        3.140(3)   . 1_655 no
 O30       C13       3.208(2)   . 1_655 no
 O30       C9        3.368(3)   . 1_655 no
 O30       C12       3.387(2)   . 1_655 no
 O30       C14       3.450(2)   . 1_655 no
 O30       C1        3.544(2)   . . no
 O30       C3        3.546(2)   . . no
 O31       O31       2.759(3)   . 2_766 no
 O31       C17       3.276(3)   . 2_666 no
 O31       C15       3.353(2)   . 1_655 no
 O31       C19       3.385(2)   . 1_655 no
 O31       C14       3.564(2)   . 1_655 no
 O33       C9        3.048(2)   . 2_666 no
 O33       O33       3.197(2)   . 2_767 no
 O33       C1        3.286(2)   . 2_666 no
 O33       C20       3.478(2)   . 2_666 no
 O33       C11       3.487(2)   . 2_666 no
 O33       N32       3.530(2)   . 2_767 no
 O34       C17       3.283(3)   . 2_667 no
 O34       C17       3.326(3)   . . no
 O34       C2        3.483(3)   . 1_556 no
 O34       C9        3.590(2)   . 1_656 no
 O36       C5        3.354(2)   . 4_566 no
 O37       C12       3.171(3)   . 4_565 no
 O37       C12       3.359(2)   . . no
 O37       C13       3.363(2)   . . no
 N29       C14       3.301(2)   . 1_655 no
 N29       C13       3.496(2)   . 1_655 no
 N29       C15       3.527(2)   . 1_655 no
 C14       C23       3.599(2)   . 1_455 no
 C15       C26       3.553(2)   . . no
 C19       C26       3.425(2)   . . no
 C19       C25       3.446(2)   . . no
#------------------------------------------------------------------------------

_iucr_refine_instruction_details_constraints
;
#
# Punched on 08/03/13 at 16:23:38
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT C    (    1 ,X'S,U'S)  UNTIL O    (   37 ) 
CONT H    (   11 ,X'S)  UNTIL H    (  401 ) 
END                                                                             
;


_iucr_refine_instruction_details_restraints
;
#
# Punched on 08/03/13 at 16:23:38
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;





#===END

