#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:15:34 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180419 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/88/7208860.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_7208860
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
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                116.322(4)
_cell_angle_beta                 93.538(4)
_cell_angle_gamma                108.236(4)
_cell_formula_units_Z            2
_cell_length_a                   7.352(2)
_cell_length_b                   9.030(3)
_cell_length_c                   9.219(3)
_cell_measurement_reflns_used    1031
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.419
_cell_measurement_theta_min      2.536
_cell_volume                     506.4(3)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  0.0149
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2665
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plan
_exptl_crystal_F_000             222
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1842
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0660
_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)+(0.0754P)²+0.3830P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1693
_refine_ls_wR_factor_ref         0.1780
_reflns_number_gt                1530
_reflns_number_total             1842
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce25759a.txt
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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        506.3(3)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7208860
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.3366(4) 0.9502(4) 1.2918(3) 0.0513(7) Uani 1 1 d .
H1 H 0.3775 1.0242 1.4066 0.062 Uiso 1 1 calc R
C2 C 0.3172(4) 1.0267(3) 1.1949(3) 0.0429(6) Uani 1 1 d .
H2 H 0.3473 1.1490 1.2443 0.052 Uiso 1 1 calc R
C3 C 0.2531(4) 0.9223(3) 1.0250(3) 0.0460(6) Uani 1 1 d .
C4 C 0.2180(9) 0.7444(4) 0.9632(4) 0.1098(18) Uani 1 1 d .
H4 H 0.1760 0.6670 0.8489 0.132 Uiso 1 1 calc R
C5 C 0.2448(8) 0.6806(5) 1.0697(5) 0.1082(18) Uani 1 1 d .
H5 H 0.2217 0.5597 1.0235 0.130 Uiso 1 1 calc R
C6 C 0.1485(4) 0.8903(4) 0.7461(3) 0.0523(7) Uani 1 1 d .
H6 H 0.1254 0.7694 0.6996 0.063 Uiso 1 1 calc R
C7 C 0.2192(4) 0.9950(3) 0.9145(3) 0.0439(6) Uani 1 1 d .
C8 C 0.2525(8) 1.1710(4) 0.9710(4) 0.1002(16) Uani 1 1 d .
H8 H 0.3028 1.2494 1.0845 0.120 Uiso 1 1 calc R
C9 C 0.1473(4) 1.1225(4) 0.7165(4) 0.0586(8) Uani 1 1 d .
H9 H 0.1201 1.1666 0.6473 0.070 Uiso 1 1 calc R
C10 C 0.6501(4) 0.4644(3) 0.5607(3) 0.0390(6) Uani 1 1 d .
C11 C 0.4718(4) 0.4292(3) 0.6054(3) 0.0406(6) Uani 1 1 d .
H11 H 0.4524 0.3821 0.6773 0.049 Uiso 1 1 calc R
C12 C 0.3223(4) 0.4632(3) 0.5445(3) 0.0411(6) Uani 1 1 d .
H12 H 0.2025 0.4372 0.5744 0.049 Uiso 1 1 calc R
N1 N 0.3011(4) 0.7794(3) 1.2330(3) 0.0629(7) Uani 1 1 d .
N2 N 0.1106(4) 0.9506(4) 0.6449(3) 0.0614(7) Uani 1 1 d .
N3 N 0.2177(6) 1.2374(4) 0.8743(4) 0.0970(12) Uani 1 1 d .
O1 O 0.8022(3) 0.4323(3) 0.6166(3) 0.0585(6) Uani 1 1 d .
H1A H 0.7618 0.3681 0.6579 0.088 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 124.4(3) . .
N1 C1 H1 117.8 . .
C2 C1 H1 117.8 . .
C3 C2 C1 119.9(2) . .
C3 C2 H2 120.0 . .
C1 C2 H2 120.0 . .
C4 C3 C2 115.8(2) . .
C4 C3 C7 121.7(2) . .
C2 C3 C7 122.5(2) . .
C3 C4 C5 120.1(3) . .
C3 C4 H4 120.0 . .
C5 C4 H4 120.0 . .
N1 C5 C4 124.3(3) . .
N1 C5 H5 117.9 . .
C4 C5 H5 117.9 . .
N2 C6 C7 124.0(3) . .
N2 C6 H6 118.0 . .
C7 C6 H6 118.0 . .
C8 C7 C6 113.9(3) . .
C8 C7 C3 123.5(2) . .
C6 C7 C3 122.7(2) . .
N3 C8 C7 124.2(3) . .
N3 C8 H8 117.9 . .
C7 C8 H8 117.9 . .
N3 C9 N2 126.7(3) . .
N3 C9 H9 116.6 . .
N2 C9 H9 116.6 . .
O1 C10 C11 123.1(2) . .
O1 C10 C12 118.0(2) . 2_666
C11 C10 C12 118.9(2) . 2_666
C12 C11 C10 120.8(2) . .
C12 C11 H11 119.6 . .
C10 C11 H11 119.6 . .
C11 C12 C10 120.3(2) . 2_666
C11 C12 H12 119.8 . .
C10 C12 H12 119.8 2_666 .
C1 N1 C5 115.4(3) . .
C9 N2 C6 115.6(3) . .
C9 N3 C8 115.6(3) . .
C10 O1 H1A 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 1.316(4) .
C1 C2 1.374(4) .
C1 H1 0.9300 .
C2 C3 1.373(3) .
C2 H2 0.9300 .
C3 C4 1.372(4) .
C3 C7 1.481(3) .
C4 C5 1.373(5) .
C4 H4 0.9300 .
C5 N1 1.317(4) .
C5 H5 0.9300 .
C6 N2 1.326(3) .
C6 C7 1.366(4) .
C6 H6 0.9300 .
C7 C8 1.365(4) .
C8 N3 1.328(4) .
C8 H8 0.9300 .
C9 N3 1.301(4) .
C9 N2 1.313(4) .
C9 H9 0.9300 .
C10 O1 1.365(3) .
C10 C11 1.383(4) .
C10 C12 1.383(3) 2_666
C11 C12 1.380(3) .
C11 H11 0.9300 .
C12 C10 1.383(3) 2_666
C12 H12 0.9300 .
O1 H1A 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
_geom_hbond_site_symmetry_A
O1 H1A N1 0.82 1.96 2.780(3) 173.0 2_667
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 1.4(5) . .
C1 C2 C3 C4 -1.9(5) . .
C1 C2 C3 C7 176.7(3) . .
C2 C3 C4 C5 0.8(7) . .
C7 C3 C4 C5 -177.8(4) . .
C3 C4 C5 N1 1.0(9) . .
N2 C6 C7 C8 -1.4(5) . .
N2 C6 C7 C3 177.7(3) . .
C4 C3 C7 C8 -179.9(4) . .
C2 C3 C7 C8 1.5(5) . .
C4 C3 C7 C6 1.1(5) . .
C2 C3 C7 C6 -177.5(3) . .
C6 C7 C8 N3 1.0(7) . .
C3 C7 C8 N3 -178.0(4) . .
O1 C10 C11 C12 -179.6(2) . .
C12 C10 C11 C12 0.9(4) 2_666 .
C10 C11 C12 C10 -0.9(4) . 2_666
C2 C1 N1 C5 0.5(5) . .
C4 C5 N1 C1 -1.6(7) . .
N3 C9 N2 C6 0.7(5) . .
C7 C6 N2 C9 0.6(5) . .
N2 C9 N3 C8 -1.0(6) . .
C7 C8 N3 C9 0.1(7) . .
