#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/91/4509159.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_4509159
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, 2(C10 H8 O)'
_chemical_formula_sum            'C32 H28 N2 O2'
_chemical_formula_weight         472.56
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 111.272(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.9691(15)
_cell_length_b                   25.182(5)
_cell_length_c                   7.7714(16)
_cell_measurement_temperature    298(2)
_cell_volume                     1270.9(5)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7327
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.761
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rods
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2587
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0455
_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)+(0.0700P)²+0.1274P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1270
_reflns_number_gt                2086
_reflns_number_total             2587
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg800936dsup4.cif
_cod_data_source_block           ts589d
_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_sg_symbol_H-M      P2(1)/c
_cod_database_code               4509159
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1 O -0.01475(16) 0.40595(4) 1.04831(14) 0.0630(3) Uani 1 1 d .
H1O H 0.0585 0.4244 1.1580 0.076 Uiso 1 1 d R
C1 C 0.1062(2) 0.37140(5) 1.00132(17) 0.0437(3) Uani 1 1 d .
C2 C 0.3111(2) 0.36425(6) 1.10196(18) 0.0512(4) Uani 1 1 d .
H2 H 0.3726 0.3828 1.2118 0.061 Uiso 1 1 calc R
C3 C 0.4289(2) 0.32925(6) 1.04077(19) 0.0558(4) Uani 1 1 d .
H3 H 0.5680 0.3248 1.1106 0.067 Uiso 1 1 calc R
C4 C 0.3429(2) 0.30167(6) 0.8811(2) 0.0535(4) Uani 1 1 d .
H4 H 0.4238 0.2791 0.8412 0.064 Uiso 1 1 calc R
C5 C 0.0344(3) 0.27846(6) 0.6097(2) 0.0589(4) Uani 1 1 d .
H5 H 0.1121 0.2553 0.5680 0.071 Uiso 1 1 calc R
C6 C -0.1696(3) 0.28403(6) 0.5107(2) 0.0673(5) Uani 1 1 d .
H6 H -0.2299 0.2650 0.4018 0.081 Uiso 1 1 calc R
C7 C -0.2891(2) 0.31822(6) 0.5713(2) 0.0619(4) Uani 1 1 d .
H7 H -0.4292 0.3215 0.5033 0.074 Uiso 1 1 calc R
C8 C -0.2023(2) 0.34693(6) 0.72947(19) 0.0487(3) Uani 1 1 d .
H8 H -0.2835 0.3698 0.7680 0.058 Uiso 1 1 calc R
C9 C 0.00939(19) 0.34225(5) 0.83493(16) 0.0397(3) Uani 1 1 d .
C10 C 0.1314(2) 0.30714(5) 0.77539(17) 0.0438(3) Uani 1 1 d .
N11 N 0.19025(18) 0.45602(5) 0.37362(15) 0.0509(3) Uani 1 1 d .
C11 C 0.2118(2) 0.50742(6) 0.41538(19) 0.0496(3) Uani 1 1 d .
H11 H 0.1800 0.5318 0.3193 0.060 Uiso 1 1 calc R
C12 C 0.2792(2) 0.52636(5) 0.59431(18) 0.0484(3) Uani 1 1 d .
H12 H 0.2905 0.5627 0.6163 0.058 Uiso 1 1 calc R
C13 C 0.3297(2) 0.49125(5) 0.74072(17) 0.0449(3) Uani 1 1 d .
C14 C 0.3117(2) 0.43780(6) 0.69719(18) 0.0496(3) Uani 1 1 d .
H14 H 0.3474 0.4124 0.7905 0.060 Uiso 1 1 calc R
C15 C 0.2407(2) 0.42238(6) 0.51530(19) 0.0525(4) Uani 1 1 d .
H15 H 0.2270 0.3862 0.4895 0.063 Uiso 1 1 calc R
C16 C 0.3933(2) 0.50929(6) 0.93940(19) 0.0562(4) Uani 1 1 d .
H16A H 0.2943 0.4961 0.9902 0.067 Uiso 1 1 calc R
H16B H 0.3895 0.5478 0.9423 0.067 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_3
O1 C1 C2 123.67(12) .
O1 C1 C9 116.13(11) .
C2 C1 C9 120.20(12) .
C1 C2 C3 120.49(12) .
C4 C3 C2 120.94(13) .
C3 C4 C10 120.28(13) .
C6 C5 C10 121.33(14) .
C5 C6 C7 120.29(14) .
C8 C7 C6 120.52(15) .
C7 C8 C9 120.57(13) .
C8 C9 C10 119.24(12) .
C8 C9 C1 122.39(12) .
C10 C9 C1 118.37(12) .
C4 C10 C9 119.70(12) .
C4 C10 C5 122.24(13) .
C9 C10 C5 118.05(13) .
C11 N11 C15 116.42(11) .
N11 C11 C12 123.30(13) .
C11 C12 C13 119.99(13) .
C12 C13 C14 116.62(12) .
C12 C13 C16 122.73(12) .
C14 C13 C16 120.60(12) .
C15 C14 C13 119.60(13) .
N11 C15 C14 124.03(13) .
C13 C16 C16 113.54(14) 3_667
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.3508(15) .
C1 C2 1.3686(19) .
C1 C9 1.4258(17) .
C2 C3 1.400(2) .
C3 C4 1.357(2) .
C4 C10 1.410(2) .
C5 C6 1.356(2) .
C5 C10 1.4160(19) .
C6 C7 1.394(2) .
C7 C8 1.364(2) .
C8 C9 1.4088(19) .
C9 C10 1.4158(18) .
N11 C11 1.3295(19) .
N11 C15 1.3315(18) .
C11 C12 1.3813(18) .
C12 C13 1.3819(19) .
C13 C14 1.3824(19) .
C13 C16 1.5134(18) .
C14 C15 1.3734(19) .
C16 C16 1.517(3) 3_667
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 H1O N11 0.94 1.78 2.7206(15) 176.0 1_556
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
O1 C1 C2 C3 -177.40(12) .
C9 C1 C2 C3 1.5(2) .
C1 C2 C3 C4 -0.1(2) .
C2 C3 C4 C10 -1.2(2) .
C10 C5 C6 C7 -0.4(3) .
C5 C6 C7 C8 0.8(3) .
C6 C7 C8 C9 -0.4(2) .
C7 C8 C9 C10 -0.3(2) .
C7 C8 C9 C1 -179.82(13) .
O1 C1 C9 C8 -3.08(18) .
C2 C1 C9 C8 177.98(12) .
O1 C1 C9 C10 177.39(11) .
C2 C1 C9 C10 -1.55(18) .
C3 C4 C10 C9 1.1(2) .
C3 C4 C10 C5 -178.84(13) .
C8 C9 C10 C4 -179.24(12) .
C1 C9 C10 C4 0.31(18) .
C8 C9 C10 C5 0.66(18) .
C1 C9 C10 C5 -179.79(12) .
C6 C5 C10 C4 179.57(15) .
C6 C5 C10 C9 -0.3(2) .
C15 N11 C11 C12 -1.1(2) .
N11 C11 C12 C13 0.6(2) .
C11 C12 C13 C14 0.91(19) .
C11 C12 C13 C16 -176.61(13) .
C12 C13 C14 C15 -1.83(19) .
C16 C13 C14 C15 175.75(13) .
C11 N11 C15 C14 0.1(2) .
C13 C14 C15 N11 1.4(2) .
C12 C13 C16 C16 -120.56(19) 3_667
C14 C13 C16 C16 62.0(2) 3_667
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146856
