#------------------------------------------------------------------------------
#$Date: 2022-05-20 01:32:47 +0300 (Fri, 20 May 2022) $
#$Revision: 275560 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/49/7244959.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_7244959
loop_
_publ_author_name
'Kim, Paul'
'Lee, In-Seo'
'Kim, Ji-Yoon'
'Mswahili, Medard E.'
'Jeong, Young-Seob'
'Yoon, Woo-Jin'
'Yun, Ho-Seop'
'Lee, Min-Jeong'
'Choi, Guang J.'
_publ_section_title
;
 A study to discover novel pharmaceutical cocrystals of pelubiprofen with
 a machine learning approach compared
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00153E
_journal_year                    2022
_chemical_formula_moiety         'C16 H18 O3, C6 H6 N2 O'
_chemical_formula_sum            'C22 H24 N2 O4'
_chemical_formula_weight         380.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-07-30 deposited with the CCDC.	2022-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.6002(19)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.2765(12)
_cell_length_b                   6.1664(3)
_cell_length_c                   35.009(2)
_cell_measurement_reflns_used    8423
_cell_measurement_temperature    290(1)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      3.205
_cell_volume                     3945.3(4)
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      290(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-axis Rapid S'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            14588
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.241
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         3.206
_diffrn_source                   'Sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.7811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3864
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.1105
_refine_ls_R_factor_gt           0.0489
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0790P)²+1.0159P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1314
_refine_ls_wR_factor_ref         0.1792
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2019
_reflns_number_total             3864
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00153e2.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7244959
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_publcif_funding_html
;
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.32204(15) 0.4731(4) 0.58824(7) 0.0499(6) Uani 1 1 d . . . . .
C2 C 0.25958(14) 0.3929(4) 0.61285(7) 0.0520(7) Uani 1 1 d . . . . .
H2 H 0.221570 0.505039 0.612556 0.062 Uiso 1 1 calc R U . . .
C3 C 0.22582(17) 0.1870(5) 0.59692(8) 0.0713(9) Uani 1 1 d . . . . .
H3A H 0.262208 0.074806 0.596237 0.107 Uiso 1 1 calc R U . . .
H3B H 0.207623 0.213544 0.571524 0.107 Uiso 1 1 calc R U . . .
H3C H 0.186237 0.142099 0.612907 0.107 Uiso 1 1 calc R U . . .
C4 C 0.28767(14) 0.3716(4) 0.65397(7) 0.0474(6) Uani 1 1 d . . . . .
C5 C 0.27772(15) 0.5384(4) 0.67977(7) 0.0540(7) Uani 1 1 d . . . . .
H5 H 0.253756 0.663664 0.671730 0.065 Uiso 1 1 calc R U . . .
C6 C 0.30229(14) 0.5247(4) 0.71710(7) 0.0528(7) Uani 1 1 d . . . . .
H6 H 0.293969 0.639586 0.733702 0.063 Uiso 1 1 calc R U . . .
C7 C 0.33946(14) 0.3411(4) 0.73036(7) 0.0499(7) Uani 1 1 d . . . . .
C8 C 0.34782(17) 0.1716(5) 0.70448(8) 0.0619(8) Uani 1 1 d . . . . .
H8 H 0.370701 0.044664 0.712569 0.074 Uiso 1 1 calc R U . . .
C9 C 0.32300(16) 0.1866(4) 0.66700(8) 0.0590(7) Uani 1 1 d . . . . .
H9 H 0.330172 0.071015 0.650387 0.071 Uiso 1 1 calc R U . . .
C10 C 0.36688(15) 0.3139(4) 0.76973(7) 0.0551(7) Uani 1 1 d . . . . .
H10 H 0.365476 0.172374 0.778868 0.066 Uiso 1 1 calc R U . . .
C11 C 0.39350(15) 0.4597(4) 0.79451(7) 0.0522(7) Uani 1 1 d . . . . .
C12 C 0.40313(16) 0.6978(4) 0.78736(8) 0.0608(8) Uani 1 1 d . . . . .
H12A H 0.364820 0.777109 0.800295 0.073 Uiso 1 1 calc R U . . .
H12B H 0.398192 0.725979 0.760194 0.073 Uiso 1 1 calc R U . . .
C13 C 0.4771(2) 0.7791(6) 0.80128(10) 0.0861(11) Uani 1 1 d . . . . .
H13A H 0.515096 0.715685 0.785654 0.103 Uiso 1 1 calc R U . . .
H13B H 0.479216 0.935200 0.798068 0.103 Uiso 1 1 calc R U . . .
C14 C 0.4918(2) 0.7260(6) 0.84138(10) 0.0975(13) Uani 1 1 d . . . . .
H14A H 0.457691 0.805110 0.857217 0.117 Uiso 1 1 calc R U . . .
H14B H 0.540783 0.774105 0.848112 0.117 Uiso 1 1 calc R U . . .
C15 C 0.48540(19) 0.4897(6) 0.84999(9) 0.0810(10) Uani 1 1 d . . . . .
H15A H 0.482644 0.471988 0.877465 0.097 Uiso 1 1 calc R U . . .
H15B H 0.529746 0.418298 0.841649 0.097 Uiso 1 1 calc R U . . .
C16 C 0.42098(17) 0.3758(5) 0.83197(8) 0.0634(8) Uani 1 1 d . . . . .
O1 O 0.34318(12) 0.6703(3) 0.59743(5) 0.0662(6) Uani 1 1 d . . . . .
H1 H 0.378248 0.704858 0.584338 0.099 Uiso 1 1 calc R U . . .
O2 O 0.35081(12) 0.3702(3) 0.56329(6) 0.0763(6) Uani 1 1 d . . . . .
O3 O 0.39445(16) 0.2168(4) 0.84697(6) 0.0966(8) Uani 1 1 d . . . . .
C17 C 0.65903(16) 1.0917(5) 0.51905(8) 0.0599(7) Uani 1 1 d . . . . .
C18 C 0.59096(14) 0.9858(4) 0.53368(6) 0.0478(6) Uani 1 1 d . . . . .
C19 C 0.56721(16) 0.7814(4) 0.52345(8) 0.0595(7) Uani 1 1 d . . . . .
H19 H 0.593796 0.697567 0.506413 0.071 Uiso 1 1 calc R U . . .
C20 C 0.50323(17) 0.7035(5) 0.53897(8) 0.0632(8) Uani 1 1 d . . . . .
H20 H 0.487979 0.564737 0.532182 0.076 Uiso 1 1 calc R U . . .
C21 C 0.48618(17) 1.0116(5) 0.57288(8) 0.0680(8) Uani 1 1 d . . . . .
H21 H 0.458581 1.092918 0.589842 0.082 Uiso 1 1 calc R U . . .
C22 C 0.54970(17) 1.0993(5) 0.55913(8) 0.0637(8) Uani 1 1 d . . . . .
H22 H 0.564678 1.236198 0.567155 0.076 Uiso 1 1 calc R U . . .
N1 N 0.69385(13) 1.0012(4) 0.49033(6) 0.0706(7) Uani 1 1 d . . . . .
H1A H 0.732810 1.060530 0.481569 0.085 Uiso 1 1 calc R U . . .
H1B H 0.677581 0.882953 0.480379 0.085 Uiso 1 1 calc R U . . .
N2 N 0.46236(13) 0.8154(4) 0.56299(6) 0.0579(6) Uani 1 1 d . . . . .
O4 O 0.68013(14) 1.2610(4) 0.53428(7) 0.1024(9) Uani 1 1 d . . . . .
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
_geom_angle_publ_flag
O2 C1 O1 122.3(3) . . ?
O2 C1 C2 125.2(2) . . ?
O1 C1 C2 112.5(2) . . ?
C3 C2 C1 111.7(2) . . ?
C3 C2 C4 113.9(2) . . ?
C1 C2 C4 108.4(2) . . ?
C3 C2 H2 107.5 . . ?
C1 C2 H2 107.5 . . ?
C4 C2 H2 107.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C9 117.5(2) . . ?
C5 C4 C2 120.4(2) . . ?
C9 C4 C2 122.1(2) . . ?
C6 C5 C4 122.0(2) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C7 121.1(2) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C6 116.6(2) . . ?
C8 C7 C10 119.0(2) . . ?
C6 C7 C10 124.3(2) . . ?
C9 C8 C7 121.9(3) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C4 C9 C8 120.9(2) . . ?
C4 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C7 130.5(2) . . ?
C11 C10 H10 114.8 . . ?
C7 C10 H10 114.8 . . ?
C10 C11 C16 117.0(2) . . ?
C10 C11 C12 126.3(2) . . ?
C16 C11 C12 116.6(2) . . ?
C11 C12 C13 112.0(2) . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C12 112.8(3) . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 C15 113.4(3) . . ?
C13 C14 H14A 108.9 . . ?
C15 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
C15 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 C16 115.7(3) . . ?
C14 C15 H15A 108.4 . . ?
C16 C15 H15A 108.4 . . ?
C14 C15 H15B 108.4 . . ?
C16 C15 H15B 108.4 . . ?
H15A C15 H15B 107.4 . . ?
O3 C16 C11 121.8(3) . . ?
O3 C16 C15 120.6(3) . . ?
C11 C16 C15 117.5(3) . . ?
C1 O1 H1 109.5 . . ?
O4 C17 N1 122.5(3) . . ?
O4 C17 C18 118.6(2) . . ?
N1 C17 C18 119.0(2) . . ?
C22 C18 C19 117.6(3) . . ?
C22 C18 C17 117.7(2) . . ?
C19 C18 C17 124.7(2) . . ?
C18 C19 C20 118.8(3) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
N2 C20 C19 123.6(3) . . ?
N2 C20 H20 118.2 . . ?
C19 C20 H20 118.2 . . ?
N2 C21 C22 122.9(3) . . ?
N2 C21 H21 118.6 . . ?
C22 C21 H21 118.6 . . ?
C18 C22 C21 120.1(3) . . ?
C18 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C17 N1 H1A 120.0 . . ?
C17 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C20 N2 C21 117.0(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.205(3) . ?
C1 O1 1.315(3) . ?
C1 C2 1.520(4) . ?
C2 C3 1.516(4) . ?
C2 C4 1.529(3) . ?
C2 H2 0.9800 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.382(4) . ?
C4 C9 1.386(4) . ?
C5 C6 1.380(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.397(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.393(4) . ?
C7 C10 1.471(3) . ?
C8 C9 1.387(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.337(4) . ?
C10 H10 0.9300 . ?
C11 C16 1.492(4) . ?
C11 C12 1.500(4) . ?
C12 C13 1.518(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.464(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.493(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.504(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O3 1.215(4) . ?
O1 H1 0.8200 . ?
C17 O4 1.232(3) . ?
C17 N1 1.319(3) . ?
C17 C18 1.500(4) . ?
C18 C22 1.366(4) . ?
C18 C19 1.379(3) . ?
C19 C20 1.381(4) . ?
C19 H19 0.9300 . ?
C20 N2 1.325(4) . ?
C20 H20 0.9300 . ?
C21 N2 1.330(3) . ?
C21 C22 1.372(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
