#------------------------------------------------------------------------------
#$Date: 2025-08-22 14:50:14 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301863 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/88/7208859.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7208859
loop_
_publ_author_name
'Hou, Gui-Ge'
'Zhao, Hui-Juan'
'Sun, Ju-Feng'
'Lin, Dong'
'Dai, Xian-Ping'
'Han, Jing-Tian'
'Zhao, Hui'
_publ_section_title
;
 Synthesis, structure and luminescence of Co-crystals with hexagonal
 channels: arranging disposition and π--π interactions
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              577
_journal_paper_doi               10.1039/c2ce25759a
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C12 H10 N3 O'
_chemical_formula_weight         212.23
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.089(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.865(2)
_cell_length_b                   15.655(4)
_cell_length_c                   14.016(3)
_cell_measurement_reflns_used    1186
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.199
_cell_measurement_theta_min      2.473
_cell_volume                     2124.2(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'smart APEX'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5471
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.47
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1982
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0594
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0657P)²+0.8537P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1542
_reflns_number_gt                1397
_reflns_number_total             1982
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce25759a.txt
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        2124.3(8)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7208859
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.5111(3) 0.53461(17) 0.11907(19) 0.0730(7) Uani 1 1 d .
H1 H 0.5904 0.5022 0.1202 0.088 Uiso 1 1 calc R
C2 C 0.5236(2) 0.62202(16) 0.12066(18) 0.0622(7) Uani 1 1 d .
H2 H 0.6096 0.6472 0.1229 0.075 Uiso 1 1 calc R
C3 C 0.4085(2) 0.67245(15) 0.11893(14) 0.0488(5) Uani 1 1 d .
C4 C 0.2863(2) 0.62988(17) 0.1183(2) 0.0727(8) Uani 1 1 d .
H4 H 0.2056 0.6604 0.1189 0.087 Uiso 1 1 calc R
C5 C 0.2839(3) 0.54236(19) 0.1166(2) 0.0880(9) Uani 1 1 d .
H5 H 0.1997 0.5154 0.1158 0.106 Uiso 1 1 calc R
C6 C 0.5105(2) 0.81004(15) 0.07628(18) 0.0610(6) Uani 1 1 d .
H6 H 0.5763 0.7784 0.0521 0.073 Uiso 1 1 calc R
C7 C 0.4146(2) 0.76669(15) 0.11742(15) 0.0507(6) Uani 1 1 d .
C8 C 0.3244(3) 0.81794(18) 0.1549(2) 0.0791(8) Uani 1 1 d .
H8 H 0.2591 0.7920 0.1851 0.095 Uiso 1 1 calc R
C9 C 0.4216(3) 0.93610(19) 0.1062(2) 0.0886(9) Uani 1 1 d .
H9 H 0.4231 0.9953 0.1011 0.106 Uiso 1 1 calc R
C10 C 0.5000 0.32081(19) 0.2500 0.0522(8) Uani 1 2 d S
H10 H 0.5000 0.3802 0.2500 0.063 Uiso 1 2 calc SR
C11 C 0.4297(2) 0.27721(14) 0.17038(17) 0.0538(6) Uani 1 1 d .
C12 C 0.4287(3) 0.18894(15) 0.17016(19) 0.0662(7) Uani 1 1 d .
H12 H 0.3807 0.1588 0.1171 0.079 Uiso 1 1 calc R
C13 C 0.5000 0.1469(2) 0.2500 0.0756(11) Uani 1 2 d S
H13 H 0.5000 0.0875 0.2500 0.091 Uiso 1 2 calc SR
N1 N 0.3931(3) 0.49379(14) 0.11610(16) 0.0764(7) Uani 1 1 d .
N2 N 0.5142(2) 0.89454(14) 0.06925(18) 0.0811(7) Uani 1 1 d .
N3 N 0.3260(3) 0.90357(16) 0.1500(2) 0.0988(8) Uani 1 1 d .
O2 O 0.3601(2) 0.31882(11) 0.09090(12) 0.0748(6) Uani 1 1 d .
H2A H 0.3669 0.3705 0.0999 0.112 Uiso 1 1 calc R
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'
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
N1 C1 C2 123.9(2) . .
N1 C1 H1 118.0 . .
C2 C1 H1 118.0 . .
C1 C2 C3 119.9(2) . .
C1 C2 H2 120.1 . .
C3 C2 H2 120.1 . .
C4 C3 C2 116.1(2) . .
C4 C3 C7 121.5(2) . .
C2 C3 C7 122.4(2) . .
C5 C4 C3 119.8(3) . .
C5 C4 H4 120.1 . .
C3 C4 H4 120.1 . .
N1 C5 C4 124.4(3) . .
N1 C5 H5 117.8 . .
C4 C5 H5 117.8 . .
N2 C6 C7 123.5(2) . .
N2 C6 H6 118.2 . .
C7 C6 H6 118.2 . .
C8 C7 C6 114.8(2) . .
C8 C7 C3 123.1(2) . .
C6 C7 C3 122.1(2) . .
N3 C8 C7 123.3(3) . .
N3 C8 H8 118.4 . .
C7 C8 H8 118.4 . .
N2 C9 N3 127.4(3) . .
N2 C9 H9 116.3 . .
N3 C9 H9 116.3 . .
C11 C10 C11 120.5(3) . 2_655
C11 C10 H10 119.7 . .
C11 C10 H10 119.7 2_655 .
O2 C11 C10 121.6(2) . .
O2 C11 C12 118.4(2) . .
C10 C11 C12 120.0(2) . .
C13 C12 C11 118.5(3) . .
C13 C12 H12 120.8 . .
C11 C12 H12 120.8 . .
C12 C13 C12 122.6(3) 2_655 .
C12 C13 H13 118.7 2_655 .
C12 C13 H13 118.7 . .
C5 N1 C1 115.9(2) . .
C9 N2 C6 115.8(2) . .
C9 N3 C8 115.1(2) . .
C11 O2 H2A 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.322(3) .
C1 C2 1.374(3) .
C1 H1 0.9300 .
C2 C3 1.380(3) .
C2 H2 0.9300 .
C3 C4 1.376(3) .
C3 C7 1.477(3) .
C4 C5 1.371(4) .
C4 H4 0.9300 .
C5 N1 1.319(3) .
C5 H5 0.9300 .
C6 N2 1.328(3) .
C6 C7 1.378(3) .
C6 H6 0.9300 .
C7 C8 1.375(3) .
C8 N3 1.342(3) .
C8 H8 0.9300 .
C9 N2 1.307(4) .
C9 N3 1.322(4) .
C9 H9 0.9300 .
C10 C11 1.377(3) .
C10 C11 1.377(3) 2_655
C10 H10 0.9300 .
C11 O2 1.357(3) .
C11 C12 1.382(3) .
C12 C13 1.371(3) .
C12 H12 0.9300 .
C13 C12 1.371(3) 2_655
C13 H13 0.9300 .
O2 H2A 0.8200 .
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
O2 H2A N1 0.82 1.95 2.773(3) 176.1
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_4
N1 C1 C2 C3 -0.1(4) . .
C1 C2 C3 C4 1.7(3) . .
C1 C2 C3 C7 -178.1(2) . .
C2 C3 C4 C5 -1.8(4) . .
C7 C3 C4 C5 178.0(2) . .
C3 C4 C5 N1 0.4(5) . .
N2 C6 C7 C8 -2.5(4) . .
N2 C6 C7 C3 176.4(2) . .
C4 C3 C7 C8 28.1(3) . .
C2 C3 C7 C8 -152.2(2) . .
C4 C3 C7 C6 -150.6(2) . .
C2 C3 C7 C6 29.1(3) . .
C6 C7 C8 N3 1.7(4) . .
C3 C7 C8 N3 -177.1(3) . .
C11 C10 C11 O2 -179.7(2) 2_655 .
C11 C10 C11 C12 0.34(16) 2_655 .
O2 C11 C12 C13 179.38(17) . .
C10 C11 C12 C13 -0.7(3) . .
C11 C12 C13 C12 0.33(15) . 2_655
C4 C5 N1 C1 1.2(4) . .
C2 C1 N1 C5 -1.3(4) . .
N3 C9 N2 C6 0.5(5) . .
C7 C6 N2 C9 1.5(4) . .
N2 C9 N3 C8 -1.2(5) . .
C7 C8 N3 C9 0.0(5) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139196669
