#------------------------------------------------------------------------------
#$Date: 2022-10-18 01:38:09 +0300 (Tue, 18 Oct 2022) $
#$Revision: 278615 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/56/7245685.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_7245685
loop_
_publ_author_name
'Bilal, Aqsa'
'Mehmood, Arshad'
'Noureen, Sajida'
'Lecomte, Claude'
'Ahmed, Maqsood'
_publ_section_title
;
 Crystal Engineering of co-crystal of antipyrine and 2-chlorobenzoic acid:
 relative energetic contributions based on multipolar refinement
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE01179D
_journal_year                    2022
_chemical_formula_moiety         'C18 H17 Cl N2 O3'
_chemical_formula_sum            'C18 H17 Cl N2 O3'
_chemical_formula_weight         344.78
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-01-28 deposited with the CCDC.	2022-10-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.6750(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4003(3)
_cell_length_b                   7.16320(10)
_cell_length_c                   18.4777(4)
_cell_measurement_reflns_used    1200
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      45.3
_cell_measurement_theta_min      2.2
_cell_volume                     1639.51(6)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
'Bruker D8 Venture with PHOTON II Detector (Bruker, 2016)'
_diffrn_measurement_method       'omega and phi scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            119630
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         45.309
_diffrn_reflns_theta_min         2.207
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   Numerical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       needle
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.287
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.723
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         13656
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0501
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1514
_refine_ls_wR_factor_ref         0.1761
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9336
_reflns_number_total             13656
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            d2ce01179d2.cif
_cod_data_source_block           IAM_shelx
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7245685
_publcif_datablock.id            {6191ef93-2874-4269-b413-02d2823ece98}
_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+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_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
Cl1 Cl 0.84396(2) 0.50207(3) 0.45151(2) 0.02560(6) Uani 1 1 d . . . . .
N1 N 0.28227(5) 0.67434(8) 0.31793(3) 0.01288(10) Uani 1 1 d . . . . .
O1 O 0.35757(5) 0.45123(8) 0.39554(3) 0.01614(10) Uani 1 1 d . . . . .
C1 C 0.20742(5) 0.55855(10) 0.27860(4) 0.01266(10) Uani 1 1 d . . . . .
O2 O 0.51868(4) 0.29650(8) 0.46216(3) 0.01557(10) Uani 1 1 d . . . . .
H2 H 0.4628(14) 0.364(2) 0.4339(9) 0.050(5) Uiso 1 1 d . . . . .
N2 N 0.31849(5) 0.83716(8) 0.28504(4) 0.01339(10) Uani 1 1 d . . . . .
C2 C 0.20734(6) 0.55178(11) 0.20317(4) 0.01598(12) Uani 1 1 d . . . . .
H2A H 0.257249 0.624783 0.177845 0.019 Uiso 1 1 calc R U . . .
C3 C 0.13370(7) 0.43740(12) 0.16524(5) 0.01972(14) Uani 1 1 d . . . . .
H3 H 0.133018 0.432598 0.113841 0.024 Uiso 1 1 calc R U . . .
O3 O 0.62810(5) 0.41511(10) 0.38065(4) 0.02100(12) Uani 1 1 d . . . . .
C4 C 0.06102(7) 0.33001(11) 0.20260(5) 0.02143(16) Uani 1 1 d . . . . .
H4 H 0.011067 0.251354 0.176696 0.026 Uiso 1 1 calc R U . . .
C5 C 0.06153(6) 0.33786(11) 0.27787(5) 0.01986(15) Uani 1 1 d . . . . .
H5 H 0.011576 0.264737 0.303108 0.024 Uiso 1 1 calc R U . . .
C6 C 0.13456(6) 0.45186(11) 0.31646(5) 0.01580(12) Uani 1 1 d . . . . .
H6 H 0.134840 0.457045 0.367840 0.019 Uiso 1 1 calc R U . . .
C7 C 0.36431(6) 0.60720(9) 0.36526(4) 0.01209(10) Uani 1 1 d . . . . .
C8 C 0.44733(6) 0.74422(10) 0.36611(4) 0.01336(11) Uani 1 1 d . . . . .
H8 H 0.513097 0.740830 0.394587 0.016 Uiso 1 1 calc R U . . .
C9 C 0.41529(6) 0.88181(10) 0.31846(4) 0.01281(10) Uani 1 1 d . . . . .
C10 C 0.47020(7) 1.05894(12) 0.30038(5) 0.02020(14) Uani 1 1 d . . . . .
H10A H 0.469594 1.073660 0.247631 0.030 Uiso 1 1 calc R U . . .
H10B H 0.544980 1.055847 0.319989 0.030 Uiso 1 1 calc R U . . .
H10C H 0.432243 1.164164 0.321582 0.030 Uiso 1 1 calc R U . . .
C11 C 0.23813(7) 0.97431(11) 0.25975(5) 0.01732(13) Uani 1 1 d . . . . .
H11A H 0.274495 1.080527 0.238016 0.026 Uiso 1 1 calc R U . . .
H11B H 0.197546 1.017735 0.300779 0.026 Uiso 1 1 calc R U . . .
H11C H 0.188443 0.916703 0.223489 0.026 Uiso 1 1 calc R U . . .
C12 C 0.70199(6) 0.21625(9) 0.47438(4) 0.01217(10) Uani 1 1 d . . . . .
C13 C 0.67944(6) 0.04057(10) 0.50295(4) 0.01452(11) Uani 1 1 d . . . . .
H13 H 0.608132 -0.007573 0.497537 0.017 Uiso 1 1 calc R U . . .
C14 C 0.75905(7) -0.06534(11) 0.53912(5) 0.01758(13) Uani 1 1 d . . . . .
H14 H 0.742648 -0.185850 0.557044 0.021 Uiso 1 1 calc R U . . .
C15 C 0.86283(7) 0.00675(12) 0.54883(5) 0.01863(14) Uani 1 1 d . . . . .
H15 H 0.917228 -0.063723 0.574346 0.022 Uiso 1 1 calc R U . . .
C16 C 0.88734(6) 0.18182(12) 0.52128(4) 0.01762(13) Uani 1 1 d . . . . .
H16 H 0.958198 0.231128 0.528157 0.021 Uiso 1 1 calc R U . . .
C17 C 0.80758(6) 0.28420(10) 0.48365(4) 0.01454(11) Uani 1 1 d . . . . .
C18 C 0.61361(6) 0.32205(10) 0.43418(4) 0.01325(11) 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'
Cl Cl 0.1484 0.1585 '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
C7 N1 N2 108.67(5) . . ?
C7 N1 C1 124.03(6) . . ?
N2 N1 C1 118.70(6) . . ?
C2 C1 C6 120.77(7) . . ?
C2 C1 N1 120.13(6) . . ?
C6 C1 N1 119.10(7) . . ?
C18 O2 H2 110.2(10) . . ?
C9 N2 N1 107.03(5) . . ?
C9 N2 C11 124.11(6) . . ?
N1 N2 C11 118.15(6) . . ?
C3 C2 C1 119.58(7) . . ?
C3 C2 H2A 120.2 . . ?
C1 C2 H2A 120.2 . . ?
C2 C3 C4 120.02(8) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.02(7) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C6 C5 C4 120.56(7) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 119.05(8) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
O1 C7 N1 121.65(6) . . ?
O1 C7 C8 132.33(7) . . ?
N1 C7 C8 105.98(6) . . ?
C9 C8 C7 107.56(6) . . ?
C9 C8 H8 126.2 . . ?
C7 C8 H8 126.2 . . ?
N2 C9 C8 110.23(6) . . ?
N2 C9 C10 120.14(7) . . ?
C8 C9 C10 129.62(7) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 117.98(6) . . ?
C13 C12 C18 119.16(6) . . ?
C17 C12 C18 122.85(6) . . ?
C14 C13 C12 121.49(7) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C15 C14 C13 119.42(7) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 120.26(7) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 119.69(7) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C12 121.13(7) . . ?
C16 C17 Cl1 117.05(6) . . ?
C12 C17 Cl1 121.80(6) . . ?
O3 C18 O2 124.34(7) . . ?
O3 C18 C12 123.27(7) . . ?
O2 C18 C12 112.34(6) . . ?
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
Cl1 C17 1.7369(8) . ?
N1 C7 1.3957(9) . ?
N1 N2 1.3988(8) . ?
N1 C1 1.4194(9) . ?
O1 C7 1.2540(9) . ?
C1 C2 1.3944(11) . ?
C1 C6 1.3960(10) . ?
O2 C18 1.3203(9) . ?
O2 H2 0.976(18) . ?
N2 C9 1.3621(9) . ?
N2 C11 1.4605(10) . ?
C2 C3 1.3917(11) . ?
C2 H2A 0.9500 . ?
C3 C4 1.3923(13) . ?
C3 H3 0.9500 . ?
O3 C18 1.2132(9) . ?
C4 C5 1.3917(14) . ?
C4 H4 0.9500 . ?
C5 C6 1.3911(11) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.4219(10) . ?
C8 C9 1.3682(10) . ?
C8 H8 0.9500 . ?
C9 C10 1.4853(10) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.3980(10) . ?
C12 C17 1.3999(10) . ?
C12 C18 1.5004(9) . ?
C13 C14 1.3912(10) . ?
C13 H13 0.9500 . ?
C14 C15 1.3905(12) . ?
C14 H14 0.9500 . ?
C15 C16 1.3922(12) . ?
C15 H15 0.9500 . ?
C16 C17 1.3912(11) . ?
C16 H16 0.9500 . ?
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
loop_
_publcif_info_exptl_table_header_item
?
