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#$Date: 2022-06-24 10:55:52 +0300 (Fri, 24 Jun 2022) $
#$Revision: 276235 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/55/8105504.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_8105504
loop_
_publ_author_name
'Hanifa, Bibi'
'Sirajuddin, Muhammad'
'Lo, Kong Mun'
'Tiekink, Edward R.T.'
_publ_section_title
;
 Crystal structure of 4-[(3,5-dichlorophenyl)carbamoyl]butanoic acid,
 C11H11Cl2NO3
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1495
_journal_page_last               1497
_journal_paper_doi               10.1515/ncrs-2020-0368
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C11 H11 Cl2 N O3'
_chemical_formula_sum            'C11 H11 Cl2 N O3'
_chemical_formula_weight         276.11
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 100.970(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.2336(3)
_cell_length_b                   4.96040(10)
_cell_length_c                   14.3696(3)
_cell_measurement_reflns_used    6393
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.0040
_cell_measurement_theta_min      5.1980
_cell_volume                     1205.95(4)
_computing_cell_refinement       'CrysAlisPro [1]'
_computing_data_collection       'CrysAlisPro [1]'
_computing_data_reduction        'CrysAlisPro [1]'
_computing_molecular_graphics    'ORTEP-3 for Windows [4]'
_computing_publication_material  'SHELXL-2018/3 [3]'
_computing_structure_refinement  'SHELXL-2018/3 [3]'
_computing_structure_solution    'SHELXT 2014/5 [2]'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 5.2558
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14849
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.057
_diffrn_reflns_theta_max         67.057
_diffrn_reflns_theta_min         5.229
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    4.830
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.800
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'CrysAlisPro [1]'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.117
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.048
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_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     160
_refine_ls_number_reflns         2138
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0313
_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)+(0.0404P)²+0.3385P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0848
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1891
_reflns_number_total             2138
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2020-0368_suppl.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8105504
_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.
;
_shelx_estimated_absorpt_t_min   0.602
_shelx_estimated_absorpt_t_max   0.801
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 0.48564(3) 1.09295(13) 0.34310(4) 0.0735(2) Uani 1 1 d . . . . .
Cl2 Cl 0.66711(4) 0.35104(12) 0.55173(4) 0.06905(19) Uani 1 1 d . . . . .
O1 O 0.90134(8) 0.1446(3) -0.03210(11) 0.0622(4) Uani 1 1 d D . . . .
H1O H 0.9341(13) 0.044(5) -0.049(2) 0.093 Uiso 1 1 d D U . . .
O2 O 1.00358(8) 0.2343(3) 0.08242(10) 0.0561(3) Uani 1 1 d . . . . .
O3 O 0.79649(9) 0.4609(2) 0.25702(10) 0.0588(4) Uani 1 1 d . . . . .
N1 N 0.76439(9) 0.8866(3) 0.29116(11) 0.0442(3) Uani 1 1 d D . . . .
H1N H 0.7697(12) 1.055(2) 0.2800(15) 0.053 Uiso 1 1 d D U . . .
C1 C 0.93566(10) 0.2767(3) 0.04354(12) 0.0425(4) Uani 1 1 d . . . . .
C2 C 0.88343(10) 0.4812(4) 0.07677(12) 0.0444(4) Uani 1 1 d . . . . .
H2A H 0.835531 0.392675 0.086875 0.053 Uiso 1 1 calc R U . . .
H2B H 0.868459 0.614754 0.027307 0.053 Uiso 1 1 calc R U . . .
C3 C 0.92123(10) 0.6231(4) 0.16712(13) 0.0454(4) Uani 1 1 d . . . . .
H3A H 0.968509 0.715060 0.156664 0.054 Uiso 1 1 calc R U . . .
H3B H 0.937179 0.489456 0.216302 0.054 Uiso 1 1 calc R U . . .
C4 C 0.86710(11) 0.8269(3) 0.20158(14) 0.0462(4) Uani 1 1 d . . . . .
H4A H 0.899240 0.952197 0.244318 0.055 Uiso 1 1 calc R U . . .
H4B H 0.839880 0.929146 0.147572 0.055 Uiso 1 1 calc R U . . .
C5 C 0.80621(10) 0.7038(3) 0.25196(11) 0.0393(4) Uani 1 1 d . . . . .
C6 C 0.70292(10) 0.8267(3) 0.34117(12) 0.0403(4) Uani 1 1 d . . . . .
C7 C 0.63354(10) 0.9733(4) 0.32054(12) 0.0461(4) Uani 1 1 d . . . . .
H7 H 0.626884 1.106256 0.274058 0.055 Uiso 1 1 calc R U . . .
C8 C 0.57417(11) 0.9182(4) 0.37050(14) 0.0497(4) Uani 1 1 d . . . . .
C9 C 0.58288(11) 0.7261(4) 0.44066(13) 0.0520(5) Uani 1 1 d . . . . .
H9 H 0.542595 0.691507 0.473849 0.062 Uiso 1 1 calc R U . . .
C10 C 0.65333(11) 0.5862(4) 0.46028(12) 0.0480(4) Uani 1 1 d . . . . .
C11 C 0.71341(11) 0.6304(3) 0.41112(13) 0.0445(4) Uani 1 1 d . . . . .
H11 H 0.759929 0.530818 0.424534 0.053 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C1 O1 H1O 109(2) . .
C5 N1 C6 125.53(14) . .
C5 N1 H1N 119.4(15) . .
C6 N1 H1N 114.5(15) . .
O2 C1 O1 122.56(16) . .
O2 C1 C2 123.82(16) . .
O1 C1 C2 113.62(15) . .
C1 C2 C3 113.81(15) . .
C1 C2 H2A 108.8 . .
C3 C2 H2A 108.8 . .
C1 C2 H2B 108.8 . .
C3 C2 H2B 108.8 . .
H2A C2 H2B 107.7 . .
C2 C3 C4 113.49(15) . .
C2 C3 H3A 108.9 . .
C4 C3 H3A 108.9 . .
C2 C3 H3B 108.9 . .
C4 C3 H3B 108.9 . .
H3A C3 H3B 107.7 . .
C5 C4 C3 114.34(14) . .
C5 C4 H4A 108.7 . .
C3 C4 H4A 108.7 . .
C5 C4 H4B 108.7 . .
C3 C4 H4B 108.7 . .
H4A C4 H4B 107.6 . .
O3 C5 N1 123.32(15) . .
O3 C5 C4 122.86(15) . .
N1 C5 C4 113.82(14) . .
C7 C6 C11 120.87(16) . .
C7 C6 N1 118.66(15) . .
C11 C6 N1 120.45(16) . .
C6 C7 C8 118.64(17) . .
C6 C7 H7 120.7 . .
C8 C7 H7 120.7 . .
C9 C8 C7 121.94(18) . .
C9 C8 Cl1 118.80(14) . .
C7 C8 Cl1 119.25(15) . .
C8 C9 C10 117.87(16) . .
C8 C9 H9 121.1 . .
C10 C9 H9 121.1 . .
C11 C10 C9 122.21(17) . .
C11 C10 Cl2 119.10(15) . .
C9 C10 Cl2 118.68(14) . .
C10 C11 C6 118.46(17) . .
C10 C11 H11 120.8 . .
C6 C11 H11 120.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C8 1.7336(19) .
Cl2 C10 1.7391(19) .
O1 C1 1.310(2) .
O1 H1O 0.825(10) .
O2 C1 1.216(2) .
O3 C5 1.221(2) .
N1 C5 1.347(2) .
N1 C6 1.420(2) .
N1 H1N 0.859(10) .
C1 C2 1.494(2) .
C2 C3 1.511(3) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 C4 1.521(2) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 C5 1.512(2) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C6 C7 1.382(3) .
C6 C11 1.387(2) .
C7 C8 1.384(2) .
C7 H7 0.9300 .
C8 C9 1.375(3) .
C9 C10 1.380(3) .
C9 H9 0.9300 .
C10 C11 1.378(3) .
C11 H11 0.9300 .
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
O2 C1 C2 C3 -3.1(2) . . . .
O1 C1 C2 C3 176.77(15) . . . .
C1 C2 C3 C4 -178.81(14) . . . .
C2 C3 C4 C5 78.5(2) . . . .
C6 N1 C5 O3 -1.5(3) . . . .
C6 N1 C5 C4 178.97(16) . . . .
C3 C4 C5 O3 -6.4(3) . . . .
C3 C4 C5 N1 173.14(16) . . . .
C5 N1 C6 C7 -133.95(18) . . . .
C5 N1 C6 C11 47.9(3) . . . .
C11 C6 C7 C8 -0.7(3) . . . .
N1 C6 C7 C8 -178.86(16) . . . .
C6 C7 C8 C9 1.1(3) . . . .
C6 C7 C8 Cl1 -178.07(13) . . . .
C7 C8 C9 C10 -0.3(3) . . . .
Cl1 C8 C9 C10 178.95(14) . . . .
C8 C9 C10 C11 -1.1(3) . . . .
C8 C9 C10 Cl2 177.64(14) . . . .
C9 C10 C11 C6 1.5(3) . . . .
Cl2 C10 C11 C6 -177.23(13) . . . .
C7 C6 C11 C10 -0.6(3) . . . .
N1 C6 C11 C10 177.56(15) . . . .
