 
data_cd214395 
  
_audit_creation_method            SHELXL-2013 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C27 H28 Cl2 N4 O8' 
_chemical_formula_weight          607.43 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0033   0.0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0061   0.0033 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0106   0.0060 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'Cl'  'Cl'   0.1484   0.1585 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_space_group_crystal_system       orthorhombic 
_space_group_IT_number            19 
_space_group_name_H-M_alt         'P 21 21 21' 
_space_group_name_Hall            'P 2ac 2ab' 
  
_shelx_space_group_comment 
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
; 
  
loop_ 
 _space_group_symop_operation_xyz 
 'x, y, z' 
 '-x+1/2, -y, z+1/2' 
 '-x, y+1/2, -z+1/2' 
 'x+1/2, -y+1/2, -z' 
  
_cell_length_a                    12.4437(12) 
_cell_length_b                    15.4069(15) 
_cell_length_c                    15.5019(16) 
_cell_angle_alpha                 90 
_cell_angle_beta                  90 
_cell_angle_gamma                 90 
_cell_volume                      2972.0(5) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     4409 
_cell_measurement_theta_min       4.961 
_cell_measurement_theta_max       41.351 
  
_exptl_crystal_description        prismatic 
_exptl_crystal_colour             colorless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.358 
_exptl_crystal_F_000              1264 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.211 
_exptl_crystal_size_mid           0.165 
_exptl_crystal_size_min           0.114 
_exptl_absorpt_coefficient_mu     0.272 
_shelx_estimated_absorpt_T_min    ? 
_shelx_estimated_absorpt_T_max    ? 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.6575 
_exptl_absorpt_correction_T_max   0.7457 
_exptl_absorpt_process_details    sadabs 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_source                    ? 
_diffrn_measurement_device_type   'CCD area detector' 
_diffrn_measurement_method        'phi and omega scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             18110 
_diffrn_reflns_av_unetI/netI      0.0359 
_diffrn_reflns_av_R_equivalents   0.0332 
_diffrn_reflns_limit_h_min        -14 
_diffrn_reflns_limit_h_max        15 
_diffrn_reflns_limit_k_min        -19 
_diffrn_reflns_limit_k_max        18 
_diffrn_reflns_limit_l_min        -19 
_diffrn_reflns_limit_l_max        15 
_diffrn_reflns_theta_min          1.864 
_diffrn_reflns_theta_max          25.998 
_diffrn_reflns_theta_full         25.242 
_diffrn_measured_fraction_theta_max   1.000 
_diffrn_measured_fraction_theta_full  1.000 
_diffrn_reflns_Laue_measured_fraction_max    1.000 
_diffrn_reflns_Laue_measured_fraction_full   1.000 
_diffrn_reflns_point_group_measured_fraction_max   1.000 
_diffrn_reflns_point_group_measured_fraction_full  1.000 
_reflns_number_total              5831 
_reflns_number_gt                 4573 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.781 
_reflns_Friedel_fraction_max      1.000 
_reflns_Friedel_fraction_full     1.000 
  
_reflns_special_details 
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
; 
  
_computing_data_collection        'Bruker SMART' 
_computing_cell_refinement        'Bruker SMART' 
_computing_data_reduction         'Bruker SHELXTL' 
_computing_structure_solution     'Bruker SHELXTL' 
_computing_structure_refinement   'SHELXL-2013 (Sheldrick, 2013)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
  
_refine_special_details 
; 
 ? 
; 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0780P)²+0.3551P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    mixed 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        ? 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1695 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
; 
_refine_ls_abs_structure_Flack    0.03(3) 
_chemical_absolute_configuration  ad 
_refine_ls_number_reflns          5831 
_refine_ls_number_parameters      410 
_refine_ls_number_restraints      26 
_refine_ls_R_factor_all           0.0631 
_refine_ls_R_factor_gt            0.0487 
_refine_ls_wR_factor_ref          0.1408 
_refine_ls_wR_factor_gt           0.1304 
_refine_ls_goodness_of_fit_ref    1.054 
_refine_ls_restrained_S_all       1.058 
_refine_ls_shift/su_max           0.000 
_refine_ls_shift/su_mean          0.000 
  
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_adp_type 
 _atom_site_occupancy 
 _atom_site_site_symmetry_order 
 _atom_site_calc_flag 
 _atom_site_refinement_flags_posn 
 _atom_site_refinement_flags_adp 
 _atom_site_refinement_flags_occupancy 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
Cl1 Cl 0.62939(14) -0.17691(11) 0.15684(11) 0.1038(6) Uani 1 1 d . . . . . 
Cl2 Cl 0.6110(2) 0.59492(13) 0.10358(18) 0.1602(11) Uani 1 1 d . . . . . 
N1 N 1.0561(3) -0.0203(2) 0.2106(2) 0.0600(9) Uani 1 1 d . . . . . 
N2 N 0.8777(2) 0.14009(19) 0.13657(18) 0.0425(7) Uani 1 1 d . . . . . 
N3 N 0.9126(3) 0.4062(2) -0.1151(2) 0.0647(10) Uani 1 1 d . . . . . 
N4 N 0.7106(3) 0.26882(19) -0.0507(2) 0.0491(8) Uani 1 1 d . . . . . 
O1 O 1.1124(2) 0.1153(2) 0.17017(19) 0.0628(8) Uani 1 1 d . . . . . 
O2 O 0.9503(2) 0.05325(16) 0.03389(16) 0.0530(7) Uani 1 1 d . . . . . 
O3 O 0.9240(3) 0.2600(2) -0.1392(2) 0.0782(10) Uani 1 1 d . . . . . 
O4 O 0.5935(2) 0.15830(19) -0.0399(2) 0.0646(8) Uani 1 1 d . . . . . 
O5 O 0.7426(2) 0.14815(15) 0.03469(18) 0.0501(6) Uani 1 1 d . . . . . 
O6 O 0.7714(3) 0.2196(2) 0.2257(2) 0.0858(11) Uani 1 1 d . . . . . 
O7 O 0.8796(2) 0.11416(17) 0.27589(16) 0.0555(7) Uani 1 1 d . . . . . 
O8 O 0.5986(3) 0.3422(3) 0.2178(4) 0.1330(19) Uani 1 1 d D . . . . 
H8B H 0.5962 0.3002 0.2581 0.160 Uiso 1 1 d DR U . . . 
H8A H 0.5641 0.3098 0.1837 0.160 Uiso 1 1 d DR U . . . 
C1 C 0.8850(3) -0.0239(2) 0.1553(2) 0.0482(9) Uani 1 1 d . . . . . 
C2 C 0.7839(4) -0.0562(3) 0.1391(3) 0.0583(10) Uani 1 1 d . . . . . 
H2 H 0.7345 -0.0256 0.1058 0.070 Uiso 1 1 calc R U . . . 
C3 C 0.7591(4) -0.1360(3) 0.1744(3) 0.0673(12) Uani 1 1 d . . . . . 
C4 C 0.8316(5) -0.1815(3) 0.2216(3) 0.0777(15) Uani 1 1 d . . . . . 
H4 H 0.8125 -0.2354 0.2436 0.093 Uiso 1 1 calc R U . . . 
C5 C 0.9343(5) -0.1491(3) 0.2379(3) 0.0750(13) Uani 1 1 d . . . . . 
H5 H 0.9840 -0.1803 0.2703 0.090 Uiso 1 1 calc R U . . . 
C6 C 0.9591(4) -0.0690(3) 0.2039(3) 0.0555(10) Uani 1 1 d . . . . . 
C7 C 1.0462(3) 0.0580(3) 0.1712(2) 0.0490(9) Uani 1 1 d . . . . . 
C8 C 0.9364(3) 0.0587(2) 0.1236(2) 0.0441(8) Uani 1 1 d . . . . . 
C9 C 0.9327(3) 0.1359(2) -0.0032(2) 0.0456(8) Uani 1 1 d . . . . . 
H9A H 0.9056 0.1303 -0.0616 0.055 Uiso 1 1 calc R U . . . 
H9B H 0.9988 0.1692 -0.0045 0.055 Uiso 1 1 calc R U . . . 
C10 C 0.8497(3) 0.1792(2) 0.0548(2) 0.0414(8) Uani 1 1 d . . . . . 
C11 C 0.8515(3) 0.2777(2) 0.0570(2) 0.0392(8) Uani 1 1 d . . . . . 
H11A H 0.9250 0.2973 0.0642 0.047 Uiso 1 1 calc R U . . . 
H11B H 0.8104 0.2978 0.1063 0.047 Uiso 1 1 calc R U . . . 
C12 C 0.8043(3) 0.3179(2) -0.0262(2) 0.0436(8) Uani 1 1 d . . . . . 
C13 C 0.8886(3) 0.3218(3) -0.1003(3) 0.0540(10) Uani 1 1 d . . . . . 
C14 C 0.8488(4) 0.4605(3) -0.0655(3) 0.0590(11) Uani 1 1 d . . . . . 
C15 C 0.7813(3) 0.4130(2) -0.0129(3) 0.0501(9) Uani 1 1 d . . . . . 
C16 C 0.7083(4) 0.4521(3) 0.0404(3) 0.0636(11) Uani 1 1 d . . . . . 
H16 H 0.6632 0.4200 0.0760 0.076 Uiso 1 1 calc R U . . . 
C17 C 0.7049(5) 0.5435(3) 0.0385(4) 0.0909(18) Uani 1 1 d . . . . . 
C18 C 0.7727(6) 0.5905(3) -0.0122(5) 0.099(2) Uani 1 1 d . . . . . 
H18 H 0.7694 0.6508 -0.0107 0.119 Uiso 1 1 calc R U . . . 
C19 C 0.8450(5) 0.5512(3) -0.0648(4) 0.0875(17) Uani 1 1 d . . . . . 
H19 H 0.8908 0.5837 -0.0995 0.105 Uiso 1 1 calc R U . . . 
C20 C 0.9954(5) 0.4343(5) -0.1743(4) 0.102(2) Uani 1 1 d . . . . . 
H20A H 1.0186 0.3859 -0.2086 0.153 Uiso 1 1 calc R U . . . 
H20B H 1.0553 0.4568 -0.1424 0.153 Uiso 1 1 calc R U . . . 
H20C H 0.9673 0.4788 -0.2114 0.153 Uiso 1 1 calc R U . . . 
C21 C 1.1494(5) -0.0465(4) 0.2605(4) 0.0916(18) Uani 1 1 d . . . . . 
H21A H 1.2030 -0.0017 0.2579 0.137 Uiso 1 1 calc R U . . . 
H21B H 1.1783 -0.0993 0.2371 0.137 Uiso 1 1 calc R U . . . 
H21C H 1.1287 -0.0558 0.3194 0.137 Uiso 1 1 calc R U . . . 
C22 C 0.6784(3) 0.1910(2) -0.0205(2) 0.0450(9) Uani 1 1 d . . . . . 
C23 C 0.8355(3) 0.1631(3) 0.2149(2) 0.0503(9) Uani 1 1 d . . . . . 
C24 C 0.8446(5) 0.1184(3) 0.3677(3) 0.0793(15) Uani 1 1 d D . . . . 
C25 C 0.9317(18) 0.0631(19) 0.4059(19) 0.082(6) Uani 0.5 1 d D U P A 1 
H25A H 1.0002 0.0902 0.3963 0.124 Uiso 0.5 1 calc R U P A 1 
H25B H 0.9309 0.0070 0.3790 0.124 Uiso 0.5 1 calc R U P A 1 
H25C H 0.9198 0.0568 0.4667 0.124 Uiso 0.5 1 calc R U P A 1 
C26 C 0.7366(16) 0.0676(18) 0.3595(14) 0.131(8) Uani 0.5 1 d D U P A 1 
H26A H 0.7136 0.0491 0.4157 0.197 Uiso 0.5 1 calc R U P A 1 
H26B H 0.7470 0.0178 0.3232 0.197 Uiso 0.5 1 calc R U P A 1 
H26C H 0.6830 0.1047 0.3346 0.197 Uiso 0.5 1 calc R U P A 1 
C27 C 0.831(2) 0.2068(15) 0.403(2) 0.123(8) Uani 0.5 1 d D U P A 1 
H27A H 0.8988 0.2363 0.4026 0.184 Uiso 0.5 1 calc R U P A 1 
H27B H 0.8048 0.2031 0.4612 0.184 Uiso 0.5 1 calc R U P A 1 
H27C H 0.7803 0.2383 0.3684 0.184 Uiso 0.5 1 calc R U P A 1 
C25' C 0.9014(19) 0.0459(19) 0.415(2) 0.084(6) Uani 0.5 1 d D U P A 2 
H25D H 0.8724 -0.0090 0.3973 0.127 Uiso 0.5 1 calc R U P A 2 
H25E H 0.8911 0.0529 0.4762 0.127 Uiso 0.5 1 calc R U P A 2 
H25F H 0.9768 0.0477 0.4022 0.127 Uiso 0.5 1 calc R U P A 2 
C26' C 0.7260(16) 0.108(2) 0.3837(14) 0.138(8) Uani 0.5 1 d D U P A 2 
H26D H 0.6877 0.1536 0.3540 0.207 Uiso 0.5 1 calc R U P A 2 
H26E H 0.7120 0.1127 0.4445 0.207 Uiso 0.5 1 calc R U P A 2 
H26F H 0.7025 0.0529 0.3630 0.207 Uiso 0.5 1 calc R U P A 2 
C27' C 0.8938(19) 0.2054(14) 0.3985(17) 0.120(8) Uani 0.5 1 d D U P A 2 
H27D H 0.9705 0.2035 0.3920 0.180 Uiso 0.5 1 calc R U P A 2 
H27E H 0.8762 0.2145 0.4582 0.180 Uiso 0.5 1 calc R U P A 2 
H27F H 0.8652 0.2521 0.3646 0.180 Uiso 0.5 1 calc R U P A 2 
H4A H 0.666(3) 0.292(3) -0.090(3) 0.053(11) Uiso 1 1 d . . . . . 
  
  
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
  
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
Cl1 C3 1.754(5) . ? 
Cl2 C17 1.735(6) . ? 
N1 C7 1.358(5) . ? 
N1 C6 1.424(6) . ? 
N1 C21 1.453(6) . ? 
N2 C23 1.369(5) . ? 
N2 C10 1.445(4) . ? 
N2 C8 1.465(5) . ? 
N3 C13 1.354(5) . ? 
N3 C14 1.385(6) . ? 
N3 C20 1.447(6) . ? 
N4 C22 1.348(5) . ? 
N4 C12 1.441(5) . ? 
N4 H4A 0.90(5) . ? 
O1 C7 1.208(5) . ? 
O2 C8 1.404(4) . ? 
O2 C9 1.414(4) . ? 
O3 C13 1.210(5) . ? 
O4 C22 1.208(4) . ? 
O5 C22 1.344(4) . ? 
O5 C10 1.450(4) . ? 
O6 C23 1.193(5) . ? 
O7 C23 1.328(5) . ? 
O7 C24 1.490(5) . ? 
O8 H8B 0.9001 . ? 
O8 H8A 0.8436 . ? 
C1 C2 1.376(6) . ? 
C1 C6 1.379(5) . ? 
C1 C8 1.508(5) . ? 
C2 C3 1.381(6) . ? 
C2 H2 0.9300 . ? 
C3 C4 1.356(7) . ? 
C4 C5 1.395(8) . ? 
C4 H4 0.9300 . ? 
C5 C6 1.376(6) . ? 
C5 H5 0.9300 . ? 
C7 C8 1.553(6) . ? 
C9 C10 1.524(5) . ? 
C9 H9A 0.9700 . ? 
C9 H9B 0.9700 . ? 
C10 C11 1.518(5) . ? 
C11 C12 1.548(5) . ? 
C11 H11A 0.9700 . ? 
C11 H11B 0.9700 . ? 
C12 C15 1.507(5) . ? 
C12 C13 1.556(6) . ? 
C14 C15 1.380(6) . ? 
C14 C19 1.399(7) . ? 
C15 C16 1.368(6) . ? 
C16 C17 1.409(7) . ? 
C16 H16 0.9300 . ? 
C17 C18 1.360(9) . ? 
C18 C19 1.358(9) . ? 
C18 H18 0.9300 . ? 
C19 H19 0.9300 . ? 
C20 H20A 0.9600 . ? 
C20 H20B 0.9600 . ? 
C20 H20C 0.9600 . ? 
C21 H21A 0.9600 . ? 
C21 H21B 0.9600 . ? 
C21 H21C 0.9600 . ? 
C24 C27 1.477(18) . ? 
C24 C25 1.50(2) . ? 
C24 C26' 1.505(19) . ? 
C24 C25' 1.514(19) . ? 
C24 C27' 1.55(2) . ? 
C24 C26 1.56(2) . ? 
C25 H25A 0.9600 . ? 
C25 H25B 0.9600 . ? 
C25 H25C 0.9600 . ? 
C26 H26A 0.9600 . ? 
C26 H26B 0.9600 . ? 
C26 H26C 0.9600 . ? 
C27 H27A 0.9600 . ? 
C27 H27B 0.9600 . ? 
C27 H27C 0.9600 . ? 
C25' H25D 0.9600 . ? 
C25' H25E 0.9600 . ? 
C25' H25F 0.9600 . ? 
C26' H26D 0.9600 . ? 
C26' H26E 0.9600 . ? 
C26' H26F 0.9600 . ? 
C27' H27D 0.9600 . ? 
C27' H27E 0.9600 . ? 
C27' H27F 0.9600 . ? 
  
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C7 N1 C6 111.0(3) . . ? 
C7 N1 C21 124.0(4) . . ? 
C6 N1 C21 124.7(4) . . ? 
C23 N2 C10 125.2(3) . . ? 
C23 N2 C8 122.3(3) . . ? 
C10 N2 C8 110.9(3) . . ? 
C13 N3 C14 111.1(3) . . ? 
C13 N3 C20 123.5(5) . . ? 
C14 N3 C20 125.5(4) . . ? 
C22 N4 C12 128.1(3) . . ? 
C22 N4 H4A 114(3) . . ? 
C12 N4 H4A 118(2) . . ? 
C8 O2 C9 109.3(3) . . ? 
C22 O5 C10 121.4(3) . . ? 
C23 O7 C24 122.3(3) . . ? 
H8B O8 H8A 89.6 . . ? 
C2 C1 C6 122.0(4) . . ? 
C2 C1 C8 129.3(4) . . ? 
C6 C1 C8 108.6(3) . . ? 
C1 C2 C3 116.9(4) . . ? 
C1 C2 H2 121.5 . . ? 
C3 C2 H2 121.5 . . ? 
C4 C3 C2 121.7(5) . . ? 
C4 C3 Cl1 120.7(4) . . ? 
C2 C3 Cl1 117.6(4) . . ? 
C3 C4 C5 121.5(4) . . ? 
C3 C4 H4 119.2 . . ? 
C5 C4 H4 119.2 . . ? 
C6 C5 C4 117.2(5) . . ? 
C6 C5 H5 121.4 . . ? 
C4 C5 H5 121.4 . . ? 
C5 C6 C1 120.7(5) . . ? 
C5 C6 N1 129.4(4) . . ? 
C1 C6 N1 109.9(3) . . ? 
O1 C7 N1 126.4(4) . . ? 
O1 C7 C8 126.0(3) . . ? 
N1 C7 C8 107.5(3) . . ? 
O2 C8 N2 104.4(3) . . ? 
O2 C8 C1 108.9(3) . . ? 
N2 C8 C1 117.8(3) . . ? 
O2 C8 C7 111.2(3) . . ? 
N2 C8 C7 112.3(3) . . ? 
C1 C8 C7 102.3(3) . . ? 
O2 C9 C10 105.0(3) . . ? 
O2 C9 H9A 110.8 . . ? 
C10 C9 H9A 110.8 . . ? 
O2 C9 H9B 110.8 . . ? 
C10 C9 H9B 110.8 . . ? 
H9A C9 H9B 108.8 . . ? 
N2 C10 O5 105.9(3) . . ? 
N2 C10 C11 113.2(3) . . ? 
O5 C10 C11 110.3(3) . . ? 
N2 C10 C9 99.9(3) . . ? 
O5 C10 C9 110.6(3) . . ? 
C11 C10 C9 116.2(3) . . ? 
C10 C11 C12 112.1(3) . . ? 
C10 C11 H11A 109.2 . . ? 
C12 C11 H11A 109.2 . . ? 
C10 C11 H11B 109.2 . . ? 
C12 C11 H11B 109.2 . . ? 
H11A C11 H11B 107.9 . . ? 
N4 C12 C15 113.1(3) . . ? 
N4 C12 C11 108.4(3) . . ? 
C15 C12 C11 110.3(3) . . ? 
N4 C12 C13 111.8(3) . . ? 
C15 C12 C13 101.1(3) . . ? 
C11 C12 C13 112.0(3) . . ? 
O3 C13 N3 126.2(4) . . ? 
O3 C13 C12 125.7(4) . . ? 
N3 C13 C12 108.1(4) . . ? 
C15 C14 N3 110.9(4) . . ? 
C15 C14 C19 120.3(5) . . ? 
N3 C14 C19 128.8(5) . . ? 
C16 C15 C14 121.9(4) . . ? 
C16 C15 C12 129.6(4) . . ? 
C14 C15 C12 108.5(4) . . ? 
C15 C16 C17 116.6(5) . . ? 
C15 C16 H16 121.7 . . ? 
C17 C16 H16 121.7 . . ? 
C18 C17 C16 121.7(6) . . ? 
C18 C17 Cl2 120.7(5) . . ? 
C16 C17 Cl2 117.6(5) . . ? 
C19 C18 C17 121.4(5) . . ? 
C19 C18 H18 119.3 . . ? 
C17 C18 H18 119.3 . . ? 
C18 C19 C14 118.2(5) . . ? 
C18 C19 H19 120.9 . . ? 
C14 C19 H19 120.9 . . ? 
N3 C20 H20A 109.5 . . ? 
N3 C20 H20B 109.5 . . ? 
H20A C20 H20B 109.5 . . ? 
N3 C20 H20C 109.5 . . ? 
H20A C20 H20C 109.5 . . ? 
H20B C20 H20C 109.5 . . ? 
N1 C21 H21A 109.5 . . ? 
N1 C21 H21B 109.5 . . ? 
H21A C21 H21B 109.5 . . ? 
N1 C21 H21C 109.5 . . ? 
H21A C21 H21C 109.5 . . ? 
H21B C21 H21C 109.5 . . ? 
O4 C22 O5 118.2(3) . . ? 
O4 C22 N4 123.0(4) . . ? 
O5 C22 N4 118.8(3) . . ? 
O6 C23 O7 126.2(4) . . ? 
O6 C23 N2 124.8(3) . . ? 
O7 C23 N2 109.0(3) . . ? 
C27 C24 O7 115.4(13) . . ? 
C27 C24 C25 117(2) . . ? 
O7 C24 C25 98.1(12) . . ? 
O7 C24 C26' 116.1(9) . . ? 
O7 C24 C25' 107.2(13) . . ? 
C26' C24 C25' 107.6(16) . . ? 
O7 C24 C27' 102.6(10) . . ? 
C26' C24 C27' 115.1(14) . . ? 
C25' C24 C27' 107.7(19) . . ? 
C27 C24 C26 113.2(15) . . ? 
O7 C24 C26 98.8(8) . . ? 
C25 C24 C26 111.7(16) . . ? 
C24 C25 H25A 109.5 . . ? 
C24 C25 H25B 109.5 . . ? 
H25A C25 H25B 109.5 . . ? 
C24 C25 H25C 109.5 . . ? 
H25A C25 H25C 109.5 . . ? 
H25B C25 H25C 109.5 . . ? 
C24 C26 H26A 109.5 . . ? 
C24 C26 H26B 109.5 . . ? 
H26A C26 H26B 109.5 . . ? 
C24 C26 H26C 109.5 . . ? 
H26A C26 H26C 109.5 . . ? 
H26B C26 H26C 109.5 . . ? 
C24 C27 H27A 109.5 . . ? 
C24 C27 H27B 109.5 . . ? 
H27A C27 H27B 109.5 . . ? 
C24 C27 H27C 109.5 . . ? 
H27A C27 H27C 109.5 . . ? 
H27B C27 H27C 109.5 . . ? 
C24 C25' H25D 109.5 . . ? 
C24 C25' H25E 109.5 . . ? 
H25D C25' H25E 109.5 . . ? 
C24 C25' H25F 109.5 . . ? 
H25D C25' H25F 109.5 . . ? 
H25E C25' H25F 109.5 . . ? 
C24 C26' H26D 109.5 . . ? 
C24 C26' H26E 109.5 . . ? 
H26D C26' H26E 109.5 . . ? 
C24 C26' H26F 109.5 . . ? 
H26D C26' H26F 109.5 . . ? 
H26E C26' H26F 109.5 . . ? 
C24 C27' H27D 109.5 . . ? 
C24 C27' H27E 109.5 . . ? 
H27D C27' H27E 109.5 . . ? 
C24 C27' H27F 109.5 . . ? 
H27D C27' H27F 109.5 . . ? 
H27E C27' H27F 109.5 . . ? 
  
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
C6 C1 C2 C3 0.5(6) . . . . ? 
C8 C1 C2 C3 177.7(4) . . . . ? 
C1 C2 C3 C4 -1.3(6) . . . . ? 
C1 C2 C3 Cl1 178.4(3) . . . . ? 
C2 C3 C4 C5 1.1(8) . . . . ? 
Cl1 C3 C4 C5 -178.6(4) . . . . ? 
C3 C4 C5 C6 -0.1(8) . . . . ? 
C4 C5 C6 C1 -0.6(7) . . . . ? 
C4 C5 C6 N1 179.5(5) . . . . ? 
C2 C1 C6 C5 0.4(6) . . . . ? 
C8 C1 C6 C5 -177.2(4) . . . . ? 
C2 C1 C6 N1 -179.6(4) . . . . ? 
C8 C1 C6 N1 2.7(5) . . . . ? 
C7 N1 C6 C5 -177.0(5) . . . . ? 
C21 N1 C6 C5 -3.1(8) . . . . ? 
C7 N1 C6 C1 3.1(5) . . . . ? 
C21 N1 C6 C1 177.0(5) . . . . ? 
C6 N1 C7 O1 175.6(4) . . . . ? 
C21 N1 C7 O1 1.6(7) . . . . ? 
C6 N1 C7 C8 -7.2(4) . . . . ? 
C21 N1 C7 C8 178.8(4) . . . . ? 
C9 O2 C8 N2 17.1(4) . . . . ? 
C9 O2 C8 C1 143.8(3) . . . . ? 
C9 O2 C8 C7 -104.2(3) . . . . ? 
C23 N2 C8 O2 170.7(3) . . . . ? 
C10 N2 C8 O2 4.4(4) . . . . ? 
C23 N2 C8 C1 49.8(5) . . . . ? 
C10 N2 C8 C1 -116.5(3) . . . . ? 
C23 N2 C8 C7 -68.6(4) . . . . ? 
C10 N2 C8 C7 125.0(3) . . . . ? 
C2 C1 C8 O2 -66.1(5) . . . . ? 
C6 C1 C8 O2 111.3(4) . . . . ? 
C2 C1 C8 N2 52.4(5) . . . . ? 
C6 C1 C8 N2 -130.2(3) . . . . ? 
C2 C1 C8 C7 176.0(4) . . . . ? 
C6 C1 C8 C7 -6.5(4) . . . . ? 
O1 C7 C8 O2 69.4(5) . . . . ? 
N1 C7 C8 O2 -107.9(3) . . . . ? 
O1 C7 C8 N2 -47.3(5) . . . . ? 
N1 C7 C8 N2 135.5(3) . . . . ? 
O1 C7 C8 C1 -174.5(4) . . . . ? 
N1 C7 C8 C1 8.3(4) . . . . ? 
C8 O2 C9 C10 -31.2(4) . . . . ? 
C23 N2 C10 O5 -72.7(4) . . . . ? 
C8 N2 C10 O5 93.2(3) . . . . ? 
C23 N2 C10 C11 48.3(5) . . . . ? 
C8 N2 C10 C11 -145.9(3) . . . . ? 
C23 N2 C10 C9 172.4(3) . . . . ? 
C8 N2 C10 C9 -21.7(4) . . . . ? 
C22 O5 C10 N2 158.5(3) . . . . ? 
C22 O5 C10 C11 35.7(4) . . . . ? 
C22 O5 C10 C9 -94.2(4) . . . . ? 
O2 C9 C10 N2 31.3(3) . . . . ? 
O2 C9 C10 O5 -79.9(3) . . . . ? 
O2 C9 C10 C11 153.3(3) . . . . ? 
N2 C10 C11 C12 -171.0(3) . . . . ? 
O5 C10 C11 C12 -52.6(4) . . . . ? 
C9 C10 C11 C12 74.2(4) . . . . ? 
C22 N4 C12 C15 -135.8(4) . . . . ? 
C22 N4 C12 C11 -13.0(5) . . . . ? 
C22 N4 C12 C13 110.9(4) . . . . ? 
C10 C11 C12 N4 41.2(4) . . . . ? 
C10 C11 C12 C15 165.6(3) . . . . ? 
C10 C11 C12 C13 -82.7(4) . . . . ? 
C14 N3 C13 O3 173.2(4) . . . . ? 
C20 N3 C13 O3 -7.6(8) . . . . ? 
C14 N3 C13 C12 -4.9(5) . . . . ? 
C20 N3 C13 C12 174.2(4) . . . . ? 
N4 C12 C13 O3 -51.8(5) . . . . ? 
C15 C12 C13 O3 -172.5(4) . . . . ? 
C11 C12 C13 O3 70.1(5) . . . . ? 
N4 C12 C13 N3 126.4(3) . . . . ? 
C15 C12 C13 N3 5.7(4) . . . . ? 
C11 C12 C13 N3 -111.8(4) . . . . ? 
C13 N3 C14 C15 1.9(5) . . . . ? 
C20 N3 C14 C15 -177.2(5) . . . . ? 
C13 N3 C14 C19 -176.7(5) . . . . ? 
C20 N3 C14 C19 4.2(8) . . . . ? 
N3 C14 C15 C16 -178.1(4) . . . . ? 
C19 C14 C15 C16 0.7(6) . . . . ? 
N3 C14 C15 C12 2.1(4) . . . . ? 
C19 C14 C15 C12 -179.2(4) . . . . ? 
N4 C12 C15 C16 55.9(5) . . . . ? 
C11 C12 C15 C16 -65.8(5) . . . . ? 
C13 C12 C15 C16 175.6(4) . . . . ? 
N4 C12 C15 C14 -124.3(4) . . . . ? 
C11 C12 C15 C14 114.1(3) . . . . ? 
C13 C12 C15 C14 -4.6(4) . . . . ? 
C14 C15 C16 C17 0.5(6) . . . . ? 
C12 C15 C16 C17 -179.7(4) . . . . ? 
C15 C16 C17 C18 -1.6(8) . . . . ? 
C15 C16 C17 Cl2 178.6(4) . . . . ? 
C16 C17 C18 C19 1.6(10) . . . . ? 
Cl2 C17 C18 C19 -178.6(5) . . . . ? 
C17 C18 C19 C14 -0.4(9) . . . . ? 
C15 C14 C19 C18 -0.8(8) . . . . ? 
N3 C14 C19 C18 177.8(5) . . . . ? 
C10 O5 C22 O4 174.2(3) . . . . ? 
C10 O5 C22 N4 -6.8(5) . . . . ? 
C12 N4 C22 O4 173.6(4) . . . . ? 
C12 N4 C22 O5 -5.3(6) . . . . ? 
C24 O7 C23 O6 6.5(7) . . . . ? 
C24 O7 C23 N2 -175.2(4) . . . . ? 
C10 N2 C23 O6 -1.4(7) . . . . ? 
C8 N2 C23 O6 -165.7(4) . . . . ? 
C10 N2 C23 O7 -179.7(3) . . . . ? 
C8 N2 C23 O7 15.9(5) . . . . ? 
C23 O7 C24 C27 -45.5(14) . . . . ? 
C23 O7 C24 C25 -171.1(12) . . . . ? 
C23 O7 C24 C26' 52.2(15) . . . . ? 
C23 O7 C24 C25' 172.5(14) . . . . ? 
C23 O7 C24 C27' -74.2(10) . . . . ? 
C23 O7 C24 C26 75.4(12) . . . . ? 
  
loop_ 
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
O8 H8A O3  0.84 2.16 2.946(6) 154.7 4_455 
C9 H9A O3  0.97 2.34 2.848(5) 111.7 . 
C11 H11A O4  0.97 2.24 3.180(4) 163.7 4 
C11 H11B O6  0.97 2.26 2.938(4) 126.0 . 
C16 H16 O8  0.93 2.63 3.506(8) 157.5 . 
C27 H27C O6  0.96 2.23 2.85(3) 121.5 . 
C26' H26D O6  0.96 2.46 3.04(3) 118.5 . 
C27' H27F O6  0.96 2.50 3.09(3) 119.6 . 
N4 H4A O1  0.90(5) 2.00(5) 2.848(4) 155(4) 4_455 
  
_refine_diff_density_max    0.555 
_refine_diff_density_min   -0.483 
_refine_diff_density_rms    0.040 
  
_shelxl_version_number 2013-4 
  
  
  
