#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/89/4508997.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_4508997
loop_
_publ_author_name
'Jayasankar, Adivaraha'
'Reddy, L. Sreenivas'
'Bethune, Sarah J.'
'Rodríguez-Hornedo, Naír'
_publ_section_title
;
 Role of Cocrystal and Solution Chemistry on the Formation and Stability
 of Cocrystals with Different Stoichiometry
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              889
_journal_paper_doi               10.1021/cg800632r
_journal_volume                  9
_journal_year                    2009
_chemical_formula_moiety         'C15 H12 N2 O, C7 H7 N O2'
_chemical_formula_sum            'C22 H19 N3 O3'
_chemical_formula_weight         373.40
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 97.7740(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.1909(4)
_cell_length_b                   18.4126(13)
_cell_length_c                   19.0481(14)
_cell_measurement_temperature    85(2)
_cell_volume                     1803.8(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART-APEX'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      85(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            44818
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         1.55
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9861
_exptl_absorpt_correction_T_min  0.9698
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
  Blessing, R. Acta Cryst. (1995) A51 33-38.
  Sheldrick, G.  SADABS (Version 2.10) Bruker/Siemens area
  detector absorption and other corrections, University of
  Gottingen, Germany 2003.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4494
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0557P)²+0.7460P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1093
_reflns_number_gt                3995
_reflns_number_total             4494
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg800632rsup1.cif
_cod_data_source_block           cbzabz
_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)/n
_cod_database_code               4508997
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
O1 O 0.84286(16) -0.04338(4) 0.07451(4) 0.01789(18) Uani 1 1 d .
O2 O 0.28077(19) 0.51767(5) 0.05400(5) 0.0261(2) Uani 1 1 d .
O3 O 0.47543(19) 0.59552(5) -0.01214(5) 0.0267(2) Uani 1 1 d .
H3 H 0.569(6) 0.5486(17) -0.0250(16) 0.112(11) Uiso 1 1 d .
N1 N 0.7697(2) 0.06499(6) 0.01956(5) 0.0184(2) Uani 1 1 d .
H1A H 0.877(3) 0.0552(9) -0.0117(8) 0.023(4) Uiso 1 1 d .
H1B H 0.702(4) 0.1084(11) 0.0208(10) 0.042(5) Uiso 1 1 d .
N2 N 0.61715(18) 0.04376(5) 0.12605(5) 0.01495(19) Uani 1 1 d .
N3 N -0.1831(2) 0.81660(6) 0.14783(6) 0.0241(2) Uani 1 1 d .
H3A H -0.168(3) 0.8620(10) 0.1288(9) 0.031(4) Uiso 1 1 d .
H3B H -0.324(3) 0.8066(9) 0.1657(9) 0.031(4) Uiso 1 1 d .
C1 C 0.7493(2) 0.01864(6) 0.07324(6) 0.0145(2) Uani 1 1 d .
C2 C 0.5987(2) -0.00034(6) 0.18734(6) 0.0150(2) Uani 1 1 d .
C3 C 0.3977(2) -0.05033(6) 0.18588(6) 0.0170(2) Uani 1 1 d .
H3C H 0.2756 -0.0556 0.1443 0.020 Uiso 1 1 calc R
C4 C 0.3750(2) -0.09261(6) 0.24507(6) 0.0196(2) Uani 1 1 d .
H4A H 0.2376 -0.1268 0.2441 0.024 Uiso 1 1 calc R
C5 C 0.5544(2) -0.08459(6) 0.30575(6) 0.0205(2) Uani 1 1 d .
H5A H 0.5387 -0.1131 0.3465 0.025 Uiso 1 1 calc R
C6 C 0.7559(2) -0.03512(6) 0.30686(6) 0.0196(2) Uani 1 1 d .
H6A H 0.8800 -0.0310 0.3482 0.024 Uiso 1 1 calc R
C7 C 0.7800(2) 0.00901(6) 0.24801(6) 0.0164(2) Uani 1 1 d .
C8 C 0.9863(2) 0.06373(6) 0.25338(6) 0.0182(2) Uani 1 1 d .
H8A H 1.1456 0.0514 0.2815 0.022 Uiso 1 1 calc R
C9 C 0.9743(2) 0.12954(6) 0.22281(6) 0.0185(2) Uani 1 1 d .
H9A H 1.1267 0.1586 0.2312 0.022 Uiso 1 1 calc R
C10 C 0.7513(2) 0.16144(6) 0.17793(6) 0.0165(2) Uani 1 1 d .
C11 C 0.7118(2) 0.23672(6) 0.17923(6) 0.0203(2) Uani 1 1 d .
H11A H 0.8328 0.2662 0.2083 0.024 Uiso 1 1 calc R
C12 C 0.5003(2) 0.26902(6) 0.13906(6) 0.0216(2) Uani 1 1 d .
H12A H 0.4771 0.3201 0.1411 0.026 Uiso 1 1 calc R
C13 C 0.3219(2) 0.22695(7) 0.09581(7) 0.0211(2) Uani 1 1 d .
H13A H 0.1766 0.2491 0.0683 0.025 Uiso 1 1 calc R
C14 C 0.3575(2) 0.15220(6) 0.09308(6) 0.0187(2) Uani 1 1 d .
H14A H 0.2360 0.1231 0.0637 0.022 Uiso 1 1 calc R
C15 C 0.5709(2) 0.12009(6) 0.13330(6) 0.0153(2) Uani 1 1 d .
C16 C 0.3196(2) 0.58088(6) 0.03386(6) 0.0194(2) Uani 1 1 d .
C17 C 0.1895(2) 0.64283(6) 0.06258(6) 0.0187(2) Uani 1 1 d .
C18 C -0.0028(2) 0.63052(6) 0.10582(6) 0.0204(2) Uani 1 1 d .
H18A H -0.0489 0.5821 0.1160 0.024 Uiso 1 1 calc R
C19 C -0.1265(2) 0.68756(7) 0.13390(6) 0.0214(2) Uani 1 1 d .
H19A H -0.2574 0.6780 0.1631 0.026 Uiso 1 1 calc R
C20 C -0.0613(2) 0.75970(6) 0.11991(6) 0.0191(2) Uani 1 1 d .
C21 C 0.1376(2) 0.77180(6) 0.07823(6) 0.0212(2) Uani 1 1 d .
H21A H 0.1895 0.8201 0.0697 0.025 Uiso 1 1 calc R
C22 C 0.2592(2) 0.71439(7) 0.04940(6) 0.0212(2) Uani 1 1 d .
H22A H 0.3910 0.7236 0.0205 0.025 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
C1 N2 C15 120.48(9)
C1 N2 C2 120.02(9)
C15 N2 C2 116.42(9)
O1 C1 N1 121.86(10)
O1 C1 N2 121.96(10)
N1 C1 N2 116.17(10)
C3 C2 C7 121.19(10)
C3 C2 N2 119.42(10)
C7 C2 N2 119.37(10)
C4 C3 C2 120.10(11)
C3 C4 C5 119.63(11)
C6 C5 C4 120.14(11)
C5 C6 C7 121.14(11)
C2 C7 C6 117.76(10)
C2 C7 C8 123.14(10)
C6 C7 C8 119.08(10)
C9 C8 C7 126.90(11)
C8 C9 C10 126.99(11)
C15 C10 C11 117.40(11)
C15 C10 C9 123.12(10)
C11 C10 C9 119.47(10)
C12 C11 C10 121.47(11)
C11 C12 C13 120.21(11)
C12 C13 C14 119.52(11)
C15 C14 C13 120.01(11)
C14 C15 C10 121.36(10)
C14 C15 N2 119.64(10)
C10 C15 N2 118.90(10)
O2 C16 O3 122.77(11)
O2 C16 C17 120.47(11)
O3 C16 C17 116.75(10)
C18 C17 C22 118.83(11)
C18 C17 C16 119.70(11)
C22 C17 C16 121.44(11)
C19 C18 C17 120.92(11)
C18 C19 C20 120.71(11)
N3 C20 C21 120.84(11)
N3 C20 C19 120.97(11)
C21 C20 C19 118.17(11)
C22 C21 C20 120.93(11)
C21 C22 C17 120.40(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2398(14)
O2 C16 1.2504(15)
O3 C16 1.2984(15)
N1 C1 1.3469(15)
N2 C1 1.3724(14)
N2 C15 1.4356(14)
N2 C2 1.4360(14)
N3 C20 1.3679(16)
C2 C3 1.3886(16)
C2 C7 1.3989(15)
C3 C4 1.3883(16)
C4 C5 1.3907(17)
C5 C6 1.3851(18)
C6 C7 1.4037(16)
C7 C8 1.4638(16)
C8 C9 1.3422(16)
C9 C10 1.4654(16)
C10 C15 1.4017(15)
C10 C11 1.4019(16)
C11 C12 1.3845(17)
C12 C13 1.3893(18)
C13 C14 1.3906(16)
C14 C15 1.3904(16)
C16 C17 1.4687(16)
C17 C18 1.3958(17)
C17 C22 1.3980(17)
C18 C19 1.3763(17)
C19 C20 1.4052(16)
C20 C21 1.4028(17)
C21 C22 1.3825(17)
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
N1 H1A O1 0.888(17) 2.016(17) 2.8967(13) 171.5(15) 3_755
N3 H3A O1 0.919(18) 2.031(18) 2.9438(14) 172.4(15) 1_465
O3 H3 O2 1.04(3) 1.59(3) 2.6181(13) 172(3) 3_665
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 68425507
