data_ying
_audit_creation_date               2019-04-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name
;

;
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Bourhis, L.J., Dolomanov, O.V., Gildea, R.J., Howard, J.A.K., Puschmann, H.
 (2015). Acta Cryst. A71, 59-75.

Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.

a) Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.
b) Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C11 H12 N4'
_chemical_formula_sum              'C11 H12 N4'
_chemical_formula_weight           200.25
_chemical_melting_point            ?
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'

_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.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             14
_space_group_name_H-M_alt          'P 1 21/c 1'
_space_group_name_Hall             '-P 2ybc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'

_cell_length_a                     9.0087(7)
_cell_length_b                     12.5422(10)
_cell_length_c                     9.4589(7)
_cell_angle_alpha                  90
_cell_angle_beta                   110.777(2)
_cell_angle_gamma                  90
_cell_volume                       999.25(13)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      6215
_cell_measurement_temperature      100(2)
_cell_measurement_theta_max        24.97
_cell_measurement_theta_min        2.42
_shelx_estimated_absorpt_T_max     0.997
_shelx_estimated_absorpt_T_min     0.996
_exptl_absorpt_coefficient_mu      0.085
_exptl_absorpt_correction_T_max    0.7453
_exptl_absorpt_correction_T_min    0.7109
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0793 before and 0.0481 after correction.
The Ratio of minimum to maximum transmission is 0.9538.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear colourless'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_modifier     .
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.331
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         cube
_exptl_crystal_F_000               424
_exptl_crystal_size_max            0.05
_exptl_crystal_size_mid            0.05
_exptl_crystal_size_min            0.04
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0360
_diffrn_reflns_av_unetI/netI       0.0226
_diffrn_reflns_Laue_measured_fraction_full  1.000
_diffrn_reflns_Laue_measured_fraction_max  0.994
_diffrn_reflns_limit_h_max         10
_diffrn_reflns_limit_h_min         -10
_diffrn_reflns_limit_k_max         15
_diffrn_reflns_limit_k_min         -15
_diffrn_reflns_limit_l_max         11
_diffrn_reflns_limit_l_min         -11
_diffrn_reflns_number              16427
_diffrn_reflns_point_group_measured_fraction_full  1.000
_diffrn_reflns_point_group_measured_fraction_max  0.994
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           25.791
_diffrn_reflns_theta_min           2.418
_diffrn_ambient_temperature        100(2)
_diffrn_detector                   'Bruker PHOTON 100'
_diffrn_detector_area_resol_mean   10.4167
_diffrn_detector_type              CMOS
_diffrn_measured_fraction_theta_full  1.000
_diffrn_measured_fraction_theta_max  0.994
_diffrn_measurement_device_type    'Bruker D8 Venture'
_diffrn_measurement_method         'omega and phi scans'
_diffrn_radiation_monochromator    mirrors
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     'micro-focus X-ray tube'
_diffrn_source_type                'INCOATEC ImuS'
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  1477
_reflns_number_total               1899
_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.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_data_collection         'APEX3 v.2015.9-0 (Bruker AXS Inc., 2015)'
_computing_data_reduction          'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics
;
OLEX2: a complete structure solution, refinement and analysis program 
Dolomanov et al., 2009

Mercury: visualization and analysis of crystal structures
Macrae, et al., 2006

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann.
J. Appl. Cryst. (2009). 42, 339-341;

C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst. (2006). 39, 453-457.
;
_computing_publication_material
;
 APEX3 v.2015.5-2 (Bruker AXS Inc., 2015)
 OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement    'XL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution      'XT 2014/5 (Sheldrick, 2015a)'
_refine_diff_density_max           0.223
_refine_diff_density_min           -0.217
_refine_diff_density_rms           0.037
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.034
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       136
_refine_ls_number_reflns           1899
_refine_ls_number_restraints       45
_refine_ls_R_factor_all            0.0576
_refine_ls_R_factor_gt             0.0390
_refine_ls_restrained_S_all        1.027
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0454P)²+0.3882P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0929
_refine_ls_wR_factor_ref           0.1028
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid body (RIGU) restrains
 C3, C2, C1, N1, N2, N3, N4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C6(H6A,H6B), C3(H3A,H3B), C2(H2A,H2B)
3.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8), C11(H11), C10(H10)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       iterative
_atom_sites_solution_secondary     ?
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
 N1 N 0.95961(15) 0.65171(10) 0.77155(14) 0.0290(3) Uani 1 1 d . U . . .
 N2 N 1.06564(16) 0.65769(14) 0.91297(16) 0.0431(4) Uani 1 1 d . U . . .
 N4 N 0.9438(2) 0.81004(13) 0.8537(2) 0.0527(5) Uani 1 1 d . U . . .
 C1 C 0.88443(19) 0.74540(11) 0.73505(18) 0.0276(4) Uani 1 1 d . U . . .
 C5 C 0.64941(17) 0.54391(12) 0.70264(17) 0.0269(4) Uani 1 1 d . . . . .
 C4 C 0.57765(18) 0.63180(12) 0.61342(15) 0.0277(4) Uani 1 1 d . . . . .
 C7 C 0.93406(18) 0.55300(12) 0.68465(17) 0.0281(4) Uani 1 1 d . . . . .
 H7A H 1.032244 0.509674 0.721110 0.034 Uiso 1 1 calc R . . . .
 H7B H 0.912219 0.570366 0.577041 0.034 Uiso 1 1 calc R . . . .
 C9 C 0.36827(18) 0.63048(13) 0.71861(17) 0.0326(4) Uani 1 1 d . . . . .
 H9 H 0.272750 0.659804 0.722950 0.039 Uiso 1 1 calc R . . . .
 C6 C 0.79621(18) 0.48725(12) 0.69704(19) 0.0320(4) Uani 1 1 d . . . . .
 H6A H 0.761419 0.437752 0.609873 0.038 Uiso 1 1 calc R . . . .
 H6B H 0.838634 0.442977 0.789351 0.038 Uiso 1 1 calc R . . . .
 C8 C 0.43878(19) 0.67353(13) 0.62377(17) 0.0325(4) Uani 1 1 d . . . . .
 H8 H 0.390962 0.733571 0.563622 0.039 Uiso 1 1 calc R . . . .
 N3 N 1.0546(2) 0.75351(18) 0.9605(2) 0.0641(6) Uani 1 1 d . U . . .
 C11 C 0.5778(2) 0.50225(13) 0.7988(2) 0.0368(4) Uani 1 1 d . . . . .
 H11 H 0.625648 0.443072 0.860896 0.044 Uiso 1 1 calc R . . . .
 C10 C 0.4390(2) 0.54419(14) 0.8069(2) 0.0373(4) Uani 1 1 d . . . . .
 H10 H 0.392598 0.513532 0.873206 0.045 Uiso 1 1 calc R . . . .
 C3 C 0.6478(2) 0.68740(15) 0.51042(18) 0.0407(5) Uani 1 1 d . U . . .
 H3A H 0.561094 0.717130 0.422446 0.049 Uiso 1 1 calc R . . . .
 H3B H 0.706776 0.635054 0.472265 0.049 Uiso 1 1 calc R . . . .
 C2 C 0.7592(2) 0.77680(14) 0.5922(2) 0.0432(5) Uani 1 1 d . U . . .
 H2A H 0.810276 0.806205 0.523619 0.052 Uiso 1 1 calc R . . . .
 H2B H 0.695435 0.834570 0.613796 0.052 Uiso 1 1 calc R . . . .


_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
 N1 N2 1.3420(19) . ?
 N1 C1 1.3390(19) . ?
 N1 C7 1.4585(19) . ?
 N2 N3 1.299(2) . ?
 N4 C1 1.333(2) . ?
 N4 N3 1.343(3) . ?
 C1 C2 1.474(2) . ?
 C5 C4 1.399(2) . ?
 C5 C6 1.519(2) . ?
 C5 C11 1.390(2) . ?
 C4 C8 1.391(2) . ?
 C4 C3 1.507(2) . ?
 C7 C6 1.529(2) . ?
 C9 C8 1.380(2) . ?
 C9 C10 1.377(2) . ?
 C11 C10 1.383(2) . ?
 C3 C2 1.521(3) . ?

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
 N2 N1 C7 121.56(13) . . ?
 C1 N1 N2 108.91(13) . . ?
 C1 N1 C7 129.45(13) . . ?
 N3 N2 N1 106.36(16) . . ?
 C1 N4 N3 106.33(15) . . ?
 N1 C1 C2 128.57(14) . . ?
 N4 C1 N1 107.54(15) . . ?
 N4 C1 C2 123.88(15) . . ?
 C4 C5 C6 124.70(14) . . ?
 C11 C5 C4 117.91(14) . . ?
 C11 C5 C6 117.33(14) . . ?
 C5 C4 C3 122.99(14) . . ?
 C8 C4 C5 119.24(15) . . ?
 C8 C4 C3 117.71(14) . . ?
 N1 C7 C6 112.62(12) . . ?
 C10 C9 C8 118.74(15) . . ?
 C5 C6 C7 119.42(13) . . ?
 C9 C8 C4 122.10(15) . . ?
 N2 N3 N4 110.86(15) . . ?
 C10 C11 C5 122.12(16) . . ?
 C9 C10 C11 119.88(16) . . ?
 C4 C3 C2 111.40(13) . . ?
 C1 C2 C3 114.95(13) . . ?

_olex2_submission_special_instructions  'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT230_ying
;
PROBLEM: Hirshfeld Test Diff for    N1       --C1       .        8.3 s.u.  
RESPONSE: caused by vibration of the nitrogen-containing ring
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# end Validation Reply Form