#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/50/2225035.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2225035
loop_
_publ_author_name
'Dutkiewicz, Grzegorz'
'Siddaraju, B. P.'
'Yathirajan, H. S.'
'Narayana, B.'
'Kubicki, Maciej'
_publ_section_title
;
 2-Chloro-N-[4-chloro-2-(2-chlorobenzoyl)phenyl]acetamide
;
_journal_coeditor_code           IS2519
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o499
_journal_paper_doi               10.1107/S1600536810003375
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H10 Cl3 N O2'
_chemical_formula_moiety         'C15 H10 Cl3 N O2'
_chemical_formula_sum            'C15 H10 Cl3 N O2'
_chemical_formula_weight         342.59
_chemical_name_systematic
;
2-Chloro-N-[4-chloro-2-(2-chlorobenzoyl)phenyl]acetamide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                70.069(8)
_cell_angle_beta                 77.604(9)
_cell_angle_gamma                70.388(8)
_cell_formula_units_Z            2
_cell_length_a                   7.5776(9)
_cell_length_b                   10.1565(10)
_cell_length_c                   10.7862(12)
_cell_measurement_reflns_used    3832
_cell_measurement_temperature    295.0(10)
_cell_measurement_theta_max      75.0835
_cell_measurement_theta_min      4.3812
_cell_volume                     730.41(15)
_computing_cell_refinement
'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_data_collection
'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_data_reduction
'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_molecular_graphics
'Stereochemical Workstation Operation Manual (Siemens, 1989)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      295.0(10)
_diffrn_detector_area_resol_mean 10.5357
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type
'Oxford Diffraction SuperNova (single source at offset) Atlas'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5245
_diffrn_reflns_theta_full        70.00
_diffrn_reflns_theta_max         75.22
_diffrn_reflns_theta_min         4.39
_exptl_absorpt_coefficient_mu    5.710
_exptl_absorpt_correction_T_max  0.319
_exptl_absorpt_correction_T_min  0.117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis Pro; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.442
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2917
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0551P)²+0.3949P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1132
_reflns_number_gt                2610
_reflns_number_total             2917
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            is2519.cif
_cod_data_source_block           I
_cod_original_cell_volume        730.47(14)
_cod_database_code               2225035
_cod_database_fobs_code          2225035
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.2330(3) 0.4690(2) 0.74281(19) 0.0407(4) Uani d . 1 . .
O O1 0.1250(3) 0.58486(19) 0.68930(16) 0.0679(5) Uani d . 1 . .
C C2 0.2780(3) 0.4324(2) 0.87982(17) 0.0347(4) Uani d . 1 . .
C C3 0.3816(3) 0.2896(2) 0.94118(19) 0.0391(4) Uani d . 1 . .
H H3 0.422(3) 0.219(2) 0.889(2) 0.043(6) Uiso d . 1 . .
C C4 0.4253(3) 0.2515(2) 1.06806(19) 0.0419(4) Uani d . 1 . .
Cl Cl4 0.55643(9) 0.07373(6) 1.14246(6) 0.05951(19) Uani d . 1 . .
C C5 0.3676(3) 0.3534(2) 1.1378(2) 0.0482(5) Uani d . 1 . .
H H5 0.393(4) 0.325(3) 1.228(3) 0.074(9) Uiso d . 1 . .
C C6 0.2645(3) 0.4939(2) 1.0804(2) 0.0454(5) Uani d . 1 . .
H H6 0.230(4) 0.562(3) 1.129(3) 0.059(7) Uiso d . 1 . .
C C7 0.2178(3) 0.5364(2) 0.95170(18) 0.0358(4) Uani d . 1 . .
N N8 0.1173(3) 0.67993(18) 0.88973(17) 0.0415(4) Uani d . 1 . .
H H8 0.094(4) 0.696(3) 0.812(3) 0.067(8) Uiso d . 1 . .
C C9 0.0393(3) 0.7935(2) 0.9426(2) 0.0448(5) Uani d . 1 . .
O O10 0.0375(3) 0.78715(18) 1.05679(17) 0.0650(5) Uani d . 1 . .
C C11 -0.0562(4) 0.9388(3) 0.8497(3) 0.0545(6) Uani d . 1 . .
H H11B -0.006(4) 1.010(3) 0.851(3) 0.066(8) Uiso d . 1 . .
H H11A -0.189(5) 0.970(4) 0.878(3) 0.083(10) Uiso d . 1 . .
Cl Cl12 -0.03818(13) 0.94573(7) 0.68136(7) 0.0826(3) Uani d . 1 . .
C C13 0.3127(3) 0.3605(2) 0.66429(18) 0.0403(4) Uani d . 1 . .
C C14 0.5017(3) 0.3148(2) 0.61956(19) 0.0465(5) Uani d . 1 . .
Cl Cl14 0.66554(9) 0.37077(10) 0.66357(7) 0.0759(2) Uani d . 1 . .
C C15 0.5645(5) 0.2289(3) 0.5339(2) 0.0701(9) Uani d . 1 . .
H H15 0.693(6) 0.200(4) 0.509(4) 0.102(12) Uiso d . 1 . .
C C16 0.4381(7) 0.1877(3) 0.4935(3) 0.0855(12) Uani d . 1 . .
H H16 0.478(5) 0.129(4) 0.433(4) 0.109(12) Uiso d . 1 . .
C C17 0.2507(8) 0.2312(4) 0.5360(3) 0.0885(12) Uani d . 1 . .
H H17 0.162(6) 0.198(4) 0.511(4) 0.110(13) Uiso d . 1 . .
C C18 0.1858(5) 0.3185(3) 0.6211(3) 0.0646(7) Uani d . 1 . .
H H18 0.054(4) 0.345(3) 0.647(3) 0.064(8) Uiso d . 1 . .
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'
N N 0.0311 0.0180 '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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 C2 . . 122.49(17) ?
O1 C1 C13 . . 116.25(17) ?
C2 C1 C13 . . 121.21(17) ?
C3 C2 C7 . . 118.78(17) ?
C3 C2 C1 . . 118.91(16) ?
C7 C2 C1 . . 122.30(17) ?
C4 C3 C2 . . 120.57(18) ?
C4 C3 H3 . . 122.2(13) ?
C2 C3 H3 . . 117.3(13) ?
C3 C4 C5 . . 120.60(19) ?
C3 C4 Cl4 . . 120.01(16) ?
C5 C4 Cl4 . . 119.38(16) ?
C6 C5 C4 . . 120.02(19) ?
C6 C5 H5 . . 119.4(18) ?
C4 C5 H5 . . 120.5(18) ?
C5 C6 C7 . . 120.93(19) ?
C5 C6 H6 . . 118.3(16) ?
C7 C6 H6 . . 120.8(16) ?
C6 C7 N8 . . 121.99(17) ?
C6 C7 C2 . . 119.09(18) ?
N8 C7 C2 . . 118.90(16) ?
C9 N8 C7 . . 128.23(18) ?
C9 N8 H8 . . 116(2) ?
C7 N8 H8 . . 116(2) ?
O10 C9 N8 . . 125.6(2) ?
O10 C9 C11 . . 117.95(19) ?
N8 C9 C11 . . 116.46(19) ?
C9 C11 Cl12 . . 116.35(15) ?
C9 C11 H11B . . 109.2(18) ?
Cl12 C11 H11B . . 106.8(18) ?
C9 C11 H11A . . 111(2) ?
Cl12 C11 H11A . . 106(2) ?
H11B C11 H11A . . 107(3) ?
C14 C13 C18 . . 118.3(2) ?
C14 C13 C1 . . 123.67(19) ?
C18 C13 C1 . . 117.5(2) ?
C13 C14 C15 . . 121.3(3) ?
C13 C14 Cl14 . . 120.50(15) ?
C15 C14 Cl14 . . 118.2(2) ?
C16 C15 C14 . . 119.6(3) ?
C16 C15 H15 . . 123(2) ?
C14 C15 H15 . . 117(2) ?
C15 C16 C17 . . 120.4(2) ?
C15 C16 H16 . . 121(2) ?
C17 C16 H16 . . 118(2) ?
C16 C17 C18 . . 120.6(3) ?
C16 C17 H17 . . 121(2) ?
C18 C17 H17 . . 119(3) ?
C13 C18 C17 . . 119.9(3) ?
C13 C18 H18 . . 123.9(17) ?
C17 C18 H18 . . 116.2(17) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 . 1.217(3) ?
C1 C2 . 1.482(2) ?
C1 C13 . 1.506(3) ?
C2 C3 . 1.401(3) ?
C2 C7 . 1.417(2) ?
C3 C4 . 1.371(3) ?
C3 H3 . 0.99(2) ?
C4 C5 . 1.383(3) ?
C4 Cl4 . 1.744(2) ?
C5 C6 . 1.374(3) ?
C5 H5 . 0.96(3) ?
C6 C7 . 1.392(3) ?
C6 H6 . 0.94(3) ?
C7 N8 . 1.401(3) ?
N8 C9 . 1.361(3) ?
N8 H8 . 0.84(3) ?
C9 O10 . 1.209(3) ?
C9 C11 . 1.514(3) ?
C11 Cl12 . 1.770(3) ?
C11 H11B . 0.93(3) ?
C11 H11A . 0.96(3) ?
C13 C14 . 1.381(3) ?
C13 C18 . 1.388(3) ?
C14 C15 . 1.387(3) ?
C14 Cl14 . 1.732(2) ?
C15 C16 . 1.363(5) ?
C15 H15 . 0.92(4) ?
C16 C17 . 1.363(6) ?
C16 H16 . 0.97(4) ?
C17 C18 . 1.392(4) ?
C17 H17 . 0.96(4) ?
C18 H18 . 0.95(3) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N8 H8 O1 . 0.84(3) 1.95(3) 2.634(2) 138(3)
C6 H6 Cl14 2_667 0.94(3) 2.87(3) 3.675(2) 143(2)
C11 H11B O10 2_577 0.93(3) 2.50(3) 3.320(3) 147(2)
C18 H18 Cl14 1_455 0.95(3) 2.84(3) 3.745(3) 161(2)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C3 . . . . 170.9(2) ?
C13 C1 C2 C3 . . . . -6.2(3) ?
O1 C1 C2 C7 . . . . -8.3(3) ?
C13 C1 C2 C7 . . . . 174.60(18) ?
C7 C2 C3 C4 . . . . -0.6(3) ?
C1 C2 C3 C4 . . . . -179.76(19) ?
C2 C3 C4 C5 . . . . 0.1(3) ?
C2 C3 C4 Cl4 . . . . -179.37(15) ?
C3 C4 C5 C6 . . . . 0.4(4) ?
Cl4 C4 C5 C6 . . . . 179.89(18) ?
C4 C5 C6 C7 . . . . -0.5(4) ?
C5 C6 C7 N8 . . . . -178.2(2) ?
C5 C6 C7 C2 . . . . 0.1(3) ?
C3 C2 C7 C6 . . . . 0.4(3) ?
C1 C2 C7 C6 . . . . 179.63(19) ?
C3 C2 C7 N8 . . . . 178.80(18) ?
C1 C2 C7 N8 . . . . -2.0(3) ?
C6 C7 N8 C9 . . . . -5.3(3) ?
C2 C7 N8 C9 . . . . 176.4(2) ?
C7 N8 C9 O10 . . . . -3.3(4) ?
C7 N8 C9 C11 . . . . 178.0(2) ?
O10 C9 C11 Cl12 . . . . 176.4(2) ?
N8 C9 C11 Cl12 . . . . -4.8(3) ?
O1 C1 C13 C14 . . . . 114.9(2) ?
C2 C1 C13 C14 . . . . -67.8(3) ?
O1 C1 C13 C18 . . . . -56.9(3) ?
C2 C1 C13 C18 . . . . 120.4(2) ?
C18 C13 C14 C15 . . . . -0.2(3) ?
C1 C13 C14 C15 . . . . -171.9(2) ?
C18 C13 C14 Cl14 . . . . 176.90(18) ?
C1 C13 C14 Cl14 . . . . 5.2(3) ?
C13 C14 C15 C16 . . . . -0.4(3) ?
Cl14 C14 C15 C16 . . . . -177.56(19) ?
C14 C15 C16 C17 . . . . 0.5(4) ?
C15 C16 C17 C18 . . . . 0.1(5) ?
C14 C13 C18 C17 . . . . 0.7(4) ?
C1 C13 C18 C17 . . . . 172.9(2) ?
C16 C17 C18 C13 . . . . -0.7(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 76146
