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#$Date: 2023-05-17 11:41:02 +0300 (Wed, 17 May 2023) $
#$Revision: 283818 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/72/8107216.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_8107216
loop_
_publ_author_name
'Zhu, Jian-Liang'
'Liu, Xing-Hai'
_publ_section_title
;
 The crystal structure of
 2-chloro-N-((2-chlorophenyl)carbamoyl)nicotinamide, C13H9Cl2N3O2
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              787
_journal_page_last               788
_journal_paper_doi               10.1515/ncrs-2022-0255
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C13 H9 Cl2 N3 O2'
_chemical_formula_sum            'C13 H9 Cl2 N3 O2'
_chemical_formula_weight         310.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 103.413(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.918(2)
_cell_length_b                   12.766(3)
_cell_length_c                   13.767(4)
_cell_measurement_reflns_used    9863
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.81
_cell_measurement_theta_min      2.20
_cell_volume                     1353.6(6)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2015)'
_diffrn_ambient_temperature      296(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_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            32412
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.935
_diffrn_reflns_theta_min         2.728
_exptl_absorpt_coefficient_mu    0.483
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. '
wR2(int) was 0.0975 before and 0.0453 after correction. The Ratio of minimum 
to maximum transmission is 0.9283. The λ/2 correction factor is Not present.'
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         4273
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0382
_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)+(0.0453P)²+0.3954P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1019
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3335
_reflns_number_total             4273
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0255_suppl.cif
_cod_data_source_block           2
_cod_database_code               8107216
_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.
;
_shelx_estimated_absorpt_t_max   0.861
_shelx_estimated_absorpt_t_min   0.801
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), C1(H1), C2(H2A), C3(H3A), C10(H10), C11(H11), C12(H12),
 C13(H13)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_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 0.49900(5) 0.86789(3) -0.27109(3) 0.04848(12) Uani 1 1 d . . . . .
Cl2 Cl 0.22056(6) 0.93774(3) 0.10238(3) 0.04862(12) Uani 1 1 d . . . . .
O1 O 0.36461(15) 0.81035(7) -0.09306(7) 0.0425(2) Uani 1 1 d . . . . .
O2 O 0.47608(18) 0.56446(8) 0.10480(8) 0.0539(3) Uani 1 1 d . . . . .
N1 N 0.34325(19) 0.72852(10) -0.39500(9) 0.0452(3) Uani 1 1 d . . . . .
N2 N 0.42703(17) 0.64016(8) -0.04786(8) 0.0372(3) Uani 1 1 d . . . . .
H2 H 0.4522 0.5809 -0.0707 0.045 Uiso 1 1 calc R . . . .
N3 N 0.39143(16) 0.73604(9) 0.08958(8) 0.0356(3) Uani 1 1 d . . . . .
H3 H 0.3648 0.7854 0.0462 0.043 Uiso 1 1 calc R . . . .
C1 C 0.2621(2) 0.63709(13) -0.42157(12) 0.0496(4) Uani 1 1 d . . . . .
H1 H 0.2280 0.6213 -0.4892 0.059 Uiso 1 1 calc R . . . .
C2 C 0.2266(2) 0.56557(12) -0.35457(12) 0.0448(3) Uani 1 1 d . . . . .
H2A H 0.1738 0.5019 -0.3760 0.054 Uiso 1 1 calc R . . . .
C3 C 0.27176(19) 0.59110(10) -0.25405(11) 0.0375(3) Uani 1 1 d . . . . .
H3A H 0.2480 0.5446 -0.2069 0.045 Uiso 1 1 calc R . . . .
C4 C 0.35281(17) 0.68634(9) -0.22343(9) 0.0298(2) Uani 1 1 d . . . . .
C5 C 0.38701(18) 0.75076(10) -0.29879(10) 0.0323(3) Uani 1 1 d . . . . .
C6 C 0.38403(17) 0.71977(10) -0.11662(9) 0.0315(3) Uani 1 1 d . . . . .
C7 C 0.43489(19) 0.64383(10) 0.05530(10) 0.0353(3) Uani 1 1 d . . . . .
C8 C 0.38419(17) 0.76180(10) 0.18816(10) 0.0320(3) Uani 1 1 d . . . . .
C9 C 0.30675(18) 0.85691(10) 0.20371(10) 0.0348(3) Uani 1 1 d . . . . .
C10 C 0.2969(2) 0.88985(13) 0.29820(12) 0.0466(4) Uani 1 1 d . . . . .
H10 H 0.2449 0.9535 0.3068 0.056 Uiso 1 1 calc R . . . .
C11 C 0.3652(2) 0.82690(16) 0.37937(12) 0.0546(4) Uani 1 1 d . . . . .
H11 H 0.3589 0.8478 0.4432 0.066 Uiso 1 1 calc R . . . .
C12 C 0.4429(2) 0.73286(15) 0.36566(11) 0.0501(4) Uani 1 1 d . . . . .
H12 H 0.4890 0.6910 0.4207 0.060 Uiso 1 1 calc R . . . .
C13 C 0.4533(2) 0.69971(12) 0.27125(11) 0.0408(3) Uani 1 1 d . . . . .
H13 H 0.5063 0.6363 0.2634 0.049 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'
Cl Cl 0.1484 0.1585 '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
C5 N1 C1 117.28(13) . .
C6 N2 H2 116.0 . .
C6 N2 C7 127.96(11) . .
C7 N2 H2 116.0 . .
C7 N3 H3 116.1 . .
C7 N3 C8 127.86(11) . .
C8 N3 H3 116.1 . .
N1 C1 H1 118.1 . .
N1 C1 C2 123.73(14) . .
C2 C1 H1 118.1 . .
C1 C2 H2A 121.0 . .
C1 C2 C3 117.98(14) . .
C3 C2 H2A 121.0 . .
C2 C3 H3A 120.0 . .
C2 C3 C4 120.09(13) . .
C4 C3 H3A 120.0 . .
C3 C4 C5 116.32(12) . .
C3 C4 C6 120.39(12) . .
C5 C4 C6 123.04(11) . .
N1 C5 Cl1 114.06(10) . .
N1 C5 C4 124.54(13) . .
C4 C5 Cl1 121.38(10) . .
O1 C6 N2 122.89(12) . .
O1 C6 C4 121.97(11) . .
N2 C6 C4 115.06(11) . .
O2 C7 N2 118.59(12) . .
O2 C7 N3 126.00(13) . .
N3 C7 N2 115.40(11) . .
C9 C8 N3 117.82(12) . .
C13 C8 N3 124.11(13) . .
C13 C8 C9 118.04(13) . .
C8 C9 Cl2 119.72(10) . .
C10 C9 Cl2 118.34(12) . .
C10 C9 C8 121.94(14) . .
C9 C10 H10 120.5 . .
C11 C10 C9 119.08(15) . .
C11 C10 H10 120.5 . .
C10 C11 H11 120.1 . .
C10 C11 C12 119.88(15) . .
C12 C11 H11 120.1 . .
C11 C12 H12 119.4 . .
C11 C12 C13 121.21(15) . .
C13 C12 H12 119.4 . .
C8 C13 H13 120.1 . .
C12 C13 C8 119.84(15) . .
C12 C13 H13 120.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C5 1.7351(14) .
Cl2 C9 1.7422(15) .
O1 C6 1.2204(15) .
O2 C7 1.2223(16) .
N1 C1 1.342(2) .
N1 C5 1.3200(18) .
N2 H2 0.8600 .
N2 C6 1.3767(16) .
N2 C7 1.4079(18) .
N3 H3 0.8600 .
N3 C7 1.3425(17) .
N3 C8 1.4104(17) .
C1 H1 0.9300 .
C1 C2 1.373(2) .
C2 H2A 0.9300 .
C2 C3 1.386(2) .
C3 H3A 0.9300 .
C3 C4 1.3937(18) .
C4 C5 1.3986(18) .
C4 C6 1.4956(18) .
C8 C9 1.3988(19) .
C8 C13 1.3950(19) .
C9 C10 1.387(2) .
C10 H10 0.9300 .
C10 C11 1.381(3) .
C11 H11 0.9300 .
C11 C12 1.382(3) .
C12 H12 0.9300 .
C12 C13 1.387(2) .
C13 H13 0.9300 .
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
N2 H2 O2 0.86 2.03 2.8819(16) 172.1 3_665
N3 H3 Cl2 0.86 2.47 2.9329(13) 114.6 .
N3 H3 O1 0.86 1.94 2.6495(16) 138.5 .
C1 H1 Cl2 0.93 2.89 3.5846(17) 132.1 2_544
C2 H2A O1 0.93 2.49 3.3785(19) 160.2 2_544
C13 H13 O2 0.93 2.33 2.908(2) 120.1 .
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
Cl2 C9 C10 C11 -179.74(13) . . . .
N1 C1 C2 C3 2.4(3) . . . .
N3 C8 C9 Cl2 0.97(17) . . . .
N3 C8 C9 C10 -178.66(13) . . . .
N3 C8 C13 C12 178.67(14) . . . .
C1 N1 C5 Cl1 177.51(12) . . . .
C1 N1 C5 C4 -0.8(2) . . . .
C1 C2 C3 C4 -0.8(2) . . . .
C2 C3 C4 C5 -1.2(2) . . . .
C2 C3 C4 C6 173.14(13) . . . .
C3 C4 C5 Cl1 -176.04(10) . . . .
C3 C4 C5 N1 2.1(2) . . . .
C3 C4 C6 O1 -140.13(15) . . . .
C3 C4 C6 N2 36.63(18) . . . .
C5 N1 C1 C2 -1.6(3) . . . .
C5 C4 C6 O1 33.8(2) . . . .
C5 C4 C6 N2 -149.40(13) . . . .
C6 N2 C7 O2 -179.97(14) . . . .
C6 N2 C7 N3 1.5(2) . . . .
C6 C4 C5 Cl1 9.76(18) . . . .
C6 C4 C5 N1 -172.07(13) . . . .
C7 N2 C6 O1 8.4(2) . . . .
C7 N2 C6 C4 -168.28(13) . . . .
C7 N3 C8 C9 -169.08(14) . . . .
C7 N3 C8 C13 12.6(2) . . . .
C8 N3 C7 O2 0.2(3) . . . .
C8 N3 C7 N2 178.67(13) . . . .
C8 C9 C10 C11 -0.1(2) . . . .
C9 C8 C13 C12 0.4(2) . . . .
C9 C10 C11 C12 0.4(3) . . . .
C10 C11 C12 C13 -0.2(3) . . . .
C11 C12 C13 C8 -0.1(2) . . . .
C13 C8 C9 Cl2 179.36(11) . . . .
C13 C8 C9 C10 -0.3(2) . . . .
