#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/91/4509160.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_4509160
loop_
_publ_author_name
'Weyna, David R.'
'Shattock, Tanise'
'Vishweshwar, Peddy'
'Zaworotko, Michael J.'
_publ_section_title
;
 Synthesis and Structural Characterization of Cocrystals and
 Pharmaceutical Cocrystals: Mechanochemistry vs Slow Evaporation from
 Solution
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1106
_journal_paper_doi               10.1021/cg800936d
_journal_volume                  9
_journal_year                    2009
_chemical_formula_moiety         'C12 H12 N2, C8 H6 O4'
_chemical_formula_sum            'C20 H18 N2 O4'
_chemical_formula_weight         350.36
_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                100.783(4)
_cell_angle_beta                 90.162(4)
_cell_angle_gamma                101.822(4)
_cell_formula_units_Z            2
_cell_length_a                   6.9526(17)
_cell_length_b                   7.4920(18)
_cell_length_c                   17.118(4)
_cell_measurement_temperature    298(2)
_cell_volume                     856.5(4)
_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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0138
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5002
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.21
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.715
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rods
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3417
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0514
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0879P)²+0.1189P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1405
_refine_ls_wR_factor_ref         0.1515
_reflns_number_gt                2860
_reflns_number_total             3417
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg800936dsup6.cif
_cod_data_source_block           ts504c
_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_sg_symbol_H-M      P-1
_cod_database_code               4509160
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
O1 O 0.62583(18) 1.22725(16) 0.34442(8) 0.0580(4) Uani 1 1 d .
O2 O 0.89079(17) 1.10361(15) 0.32271(8) 0.0572(4) Uani 1 1 d .
O3 O 0.83072(17) 0.44718(17) 0.19506(9) 0.0607(4) Uani 1 1 d .
O4 O 0.53290(17) 0.28119(16) 0.15247(8) 0.0573(4) Uani 1 1 d .
C1 C 0.5813(2) 0.9117(2) 0.27930(9) 0.0380(4) Uani 1 1 d .
C2 C 0.6687(2) 0.7613(2) 0.25402(9) 0.0376(3) Uani 1 1 d .
H2 H 0.8040 0.7749 0.2610 0.045 Uiso 1 1 calc R
C3 C 0.5542(2) 0.5901(2) 0.21823(9) 0.0378(3) Uani 1 1 d .
C4 C 0.3522(2) 0.5703(2) 0.20961(9) 0.0430(4) Uani 1 1 d .
H4 H 0.2747 0.4554 0.1871 0.052 Uiso 1 1 calc R
C5 C 0.2651(2) 0.7205(2) 0.23436(10) 0.0467(4) Uani 1 1 d .
H5 H 0.1297 0.7067 0.2279 0.056 Uiso 1 1 calc R
C6 C 0.3796(2) 0.8910(2) 0.26863(10) 0.0438(4) Uani 1 1 d .
H6 H 0.3212 0.9923 0.2846 0.053 Uiso 1 1 calc R
C7 C 0.7018(2) 1.0973(2) 0.31848(9) 0.0419(4) Uani 1 1 d .
C8 C 0.6547(2) 0.4334(2) 0.18851(9) 0.0420(4) Uani 1 1 d .
N11 N 0.7247(2) 1.01655(18) 0.09646(9) 0.0491(4) Uani 1 1 d .
C11 C 0.9145(3) 1.0367(2) 0.11745(10) 0.0489(4) Uani 1 1 d .
H11 H 0.9763 1.1459 0.1512 0.059 Uiso 1 1 calc R
C12 C 1.0231(3) 0.9046(2) 0.09175(10) 0.0467(4) Uani 1 1 d .
H12 H 1.1550 0.9253 0.1079 0.056 Uiso 1 1 calc R
C13 C 0.9348(2) 0.7399(2) 0.04143(10) 0.0442(4) Uani 1 1 d .
C14 C 0.7389(3) 0.7196(2) 0.01983(11) 0.0510(4) Uani 1 1 d .
H14 H 0.6733 0.6120 -0.0139 0.061 Uiso 1 1 calc R
C15 C 0.6403(3) 0.8593(2) 0.04828(11) 0.0523(4) Uani 1 1 d .
H15 H 0.5084 0.8424 0.0329 0.063 Uiso 1 1 calc R
C16 C 1.0556(3) 0.5971(2) 0.01249(13) 0.0593(5) Uani 1 1 d .
H16A H 1.1289 0.6330 -0.0322 0.071 Uiso 1 1 calc R
H16B H 1.1505 0.6002 0.0546 0.071 Uiso 1 1 calc R
H4O H 0.6071 0.1957 0.1348 0.071 Uiso 1 1 d R
H2O H 0.9566 1.2284 0.3508 0.071 Uiso 1 1 d R
N21 N 0.0867(2) 0.43156(18) 0.38541(8) 0.0481(4) Uani 1 1 d .
C21 C -0.0075(3) 0.5726(2) 0.40185(12) 0.0556(5) Uani 1 1 d .
H21 H -0.1421 0.5497 0.3903 0.067 Uiso 1 1 calc R
C22 C 0.0890(3) 0.7500(2) 0.43524(12) 0.0543(5) Uani 1 1 d .
H22 H 0.0190 0.8446 0.4455 0.065 Uiso 1 1 calc R
C23 C 0.2888(2) 0.7895(2) 0.45369(9) 0.0406(4) Uani 1 1 d .
C24 C 0.3844(3) 0.6426(2) 0.43619(11) 0.0477(4) Uani 1 1 d .
H24 H 0.5188 0.6611 0.4475 0.057 Uiso 1 1 calc R
C25 C 0.2787(3) 0.4681(2) 0.40175(11) 0.0494(4) Uani 1 1 d .
H25 H 0.3457 0.3717 0.3894 0.059 Uiso 1 1 calc R
C26 C 0.3914(2) 0.9863(2) 0.48882(10) 0.0437(4) Uani 1 1 d .
H26A H 0.3244 1.0291 0.5361 0.052 Uiso 1 1 calc R
H26B H 0.3776 1.0644 0.4508 0.052 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
C6 C1 C2 119.75(14) . .
C6 C1 C7 119.25(14) . .
C2 C1 C7 121.00(14) . .
C1 C2 C3 120.13(14) . .
C4 C3 C2 119.47(14) . .
C4 C3 C8 121.93(14) . .
C2 C3 C8 118.59(13) . .
C5 C4 C3 120.41(14) . .
C6 C5 C4 119.94(15) . .
C5 C6 C1 120.28(14) . .
O1 C7 O2 124.19(14) . .
O1 C7 C1 121.55(15) . .
O2 C7 C1 114.26(13) . .
O3 C8 O4 123.56(14) . .
O3 C8 C3 123.22(14) . .
O4 C8 C3 113.19(13) . .
C15 N11 C11 116.98(14) . .
N11 C11 C12 123.44(15) . .
C11 C12 C13 119.59(16) . .
C14 C13 C12 116.81(15) . .
C14 C13 C16 123.90(15) . .
C12 C13 C16 119.28(16) . .
C15 C14 C13 119.96(16) . .
N11 C15 C14 123.22(17) . .
C16 C16 C13 115.97(19) 2_765 .
C25 N21 C21 117.79(14) . .
N21 C21 C22 121.99(16) . .
C21 C22 C23 120.78(16) . .
C22 C23 C24 116.63(14) . .
C22 C23 C26 119.58(14) . .
C24 C23 C26 123.77(15) . .
C25 C24 C23 119.52(16) . .
N21 C25 C24 123.26(16) . .
C23 C26 C26 115.64(17) . 2_676
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C7 1.2146(19) .
O2 C7 1.306(2) .
O3 C8 1.210(2) .
O4 C8 1.3175(18) .
C1 C6 1.387(2) .
C1 C2 1.388(2) .
C1 C7 1.502(2) .
C2 C3 1.393(2) .
C3 C4 1.386(2) .
C3 C8 1.497(2) .
C4 C5 1.383(2) .
C5 C6 1.382(2) .
N11 C15 1.328(2) .
N11 C11 1.338(2) .
C11 C12 1.374(2) .
C12 C13 1.389(2) .
C13 C14 1.381(2) .
C13 C16 1.506(2) .
C14 C15 1.381(2) .
C16 C16 1.484(3) 2_765
N21 C25 1.325(2) .
N21 C21 1.340(2) .
C21 C22 1.376(2) .
C22 C23 1.383(2) .
C23 C24 1.386(2) .
C23 C26 1.510(2) .
C24 C25 1.383(2) .
C26 C26 1.519(3) 2_676
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
O4 H4O N11 0.91 1.74 2.6470(18) 173.7 1_545
O2 H2O N21 0.98 1.61 2.5840(18) 171.2 1_665
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_4
C6 C1 C2 C3 -0.2(2) .
C7 C1 C2 C3 179.62(13) .
C1 C2 C3 C4 -1.3(2) .
C1 C2 C3 C8 177.35(13) .
C2 C3 C4 C5 1.7(2) .
C8 C3 C4 C5 -176.91(14) .
C3 C4 C5 C6 -0.6(3) .
C4 C5 C6 C1 -0.9(3) .
C2 C1 C6 C5 1.3(2) .
C7 C1 C6 C5 -178.52(14) .
C6 C1 C7 O1 3.5(2) .
C2 C1 C7 O1 -176.26(15) .
C6 C1 C7 O2 -177.39(14) .
C2 C1 C7 O2 2.8(2) .
C4 C3 C8 O3 179.76(16) .
C2 C3 C8 O3 1.1(2) .
C4 C3 C8 O4 1.7(2) .
C2 C3 C8 O4 -176.93(13) .
C15 N11 C11 C12 0.0(3) .
N11 C11 C12 C13 -0.1(3) .
C11 C12 C13 C14 0.2(2) .
C11 C12 C13 C16 179.04(16) .
C12 C13 C14 C15 -0.1(3) .
C16 C13 C14 C15 -178.94(17) .
C11 N11 C15 C14 0.0(3) .
C13 C14 C15 N11 0.0(3) .
C14 C13 C16 C16 -24.7(3) 2_765
C12 C13 C16 C16 156.5(2) 2_765
C25 N21 C21 C22 -0.6(3) .
N21 C21 C22 C23 -0.4(3) .
C21 C22 C23 C24 0.5(3) .
C21 C22 C23 C26 178.83(17) .
C22 C23 C24 C25 0.2(2) .
C26 C23 C24 C25 -177.97(16) .
C21 N21 C25 C24 1.4(3) .
C23 C24 C25 N21 -1.3(3) .
C22 C23 C26 C26 176.83(18) 2_676
C24 C23 C26 C26 -5.0(3) 2_676
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146857
