#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/63/2216305.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_2216305
loop_
_publ_author_name
'B. Thimme Gowda'
'Sabine Foro'
'Hartmut Fuess'
_publ_section_title
;
 2,2-Dichloro-N-(2,3-dichlorophenyl)acetamide
;
_journal_coeditor_code           BT2597
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4708
_journal_page_last               o4708
_journal_paper_doi               10.1107/S1600536807057054
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C8 H5 Cl4 N O'
_chemical_formula_moiety         'C8 H5 Cl4 N O'
_chemical_formula_sum            'C8 H5 Cl4 N O'
_chemical_formula_weight         272.93
_chemical_name_systematic
;
2,2-Dichloro-N-(2,3-dichlorophenyl)acetamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.050(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.6740(10)
_cell_length_b                   11.804(2)
_cell_length_c                   19.833(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      20.27
_cell_measurement_theta_min      5.84
_cell_volume                     1090.0(3)
_computing_cell_refinement       'CAD-4-PC Software (Enraf--Nonius, 1996)'
_computing_data_collection       'CAD-4-PC Software (Enraf--Nonius, 1996)'
_computing_data_reduction        'REDU4 (Stoe & Cie, 1987)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            2435
_diffrn_reflns_theta_full        66.94
_diffrn_reflns_theta_max         66.94
_diffrn_reflns_theta_min         4.36
_diffrn_standards_decay_%        1.0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    9.600
_exptl_absorpt_correction_T_max  0.7504
_exptl_absorpt_correction_T_min  0.3222
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.663
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.440
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1950
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0456
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0721P)²+0.5313P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1292
_reflns_number_gt                1421
_reflns_number_total             1950
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2597.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2216305
_cod_database_fobs_code          2216305
loop_
_symmetry_equiv_pos_as_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_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
Cl Cl1 0.8086(2) -0.02347(8) 0.21645(5) 0.0564(3) Uani d . 1
Cl Cl2 0.6830(3) -0.03704(9) 0.36898(5) 0.0763(4) Uani d . 1
Cl Cl3 0.4053(3) 0.33369(10) -0.00199(6) 0.0782(4) Uani d . 1
Cl Cl4 0.2454(3) 0.10696(11) -0.04307(5) 0.0761(4) Uani d . 1
O O1 0.0589(5) 0.1713(3) 0.09146(13) 0.0714(9) Uani d . 1
N N1 0.5159(5) 0.1646(2) 0.13964(13) 0.0395(6) Uani d . 1
H H1N 0.6933 0.1633 0.1312 0.047 Uiso calc R 1
C C1 0.4524(6) 0.1571(3) 0.20853(15) 0.0365(7) Uani d . 1
C C2 0.5814(7) 0.0733(3) 0.24928(15) 0.0378(7) Uani d . 1
C C3 0.5257(8) 0.0668(3) 0.31709(17) 0.0474(8) Uani d . 1
C C4 0.3431(9) 0.1429(4) 0.34292(17) 0.0572(10) Uani d . 1
H H4 0.3052 0.1382 0.3881 0.069 Uiso calc R 1
C C5 0.2162(9) 0.2260(4) 0.30237(19) 0.0587(10) Uani d . 1
H H5 0.0922 0.2773 0.3203 0.070 Uiso calc R 1
C C6 0.2705(8) 0.2346(3) 0.23480(18) 0.0478(8) Uani d . 1
H H6 0.1856 0.2918 0.2076 0.057 Uiso calc R 1
C C7 0.3169(7) 0.1735(3) 0.08749(16) 0.0414(7) Uani d . 1
C C8 0.4369(7) 0.1891(3) 0.01915(16) 0.0454(8) Uani d . 1
H H8 0.6398 0.1671 0.0227 0.054 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.0591(6) 0.0535(5) 0.0558(5) 0.0144(4) -0.0003(4) -0.0054(4)
Cl2 0.1161(10) 0.0611(6) 0.0478(5) -0.0047(6) -0.0142(6) 0.0150(5)
Cl3 0.1027(9) 0.0732(7) 0.0587(6) -0.0169(6) 0.0076(6) 0.0143(5)
Cl4 0.0814(8) 0.0907(8) 0.0537(5) -0.0051(6) -0.0080(5) -0.0211(5)
O1 0.0236(12) 0.143(3) 0.0475(14) -0.0033(14) 0.0037(10) 0.0094(17)
N1 0.0253(12) 0.0599(17) 0.0337(13) 0.0029(12) 0.0044(10) 0.0049(12)
C1 0.0301(15) 0.0456(17) 0.0337(15) -0.0059(13) 0.0026(12) 0.0014(13)
C2 0.0359(16) 0.0404(16) 0.0366(16) -0.0065(13) -0.0003(13) -0.0046(13)
C3 0.057(2) 0.0499(19) 0.0335(15) -0.0115(17) -0.0036(15) 0.0044(15)
C4 0.066(2) 0.074(3) 0.0332(17) -0.008(2) 0.0136(17) -0.0058(17)
C5 0.056(2) 0.073(3) 0.049(2) 0.007(2) 0.0141(17) -0.014(2)
C6 0.0415(18) 0.055(2) 0.0468(18) 0.0075(16) 0.0043(15) 0.0019(16)
C7 0.0292(15) 0.059(2) 0.0363(16) 0.0010(14) 0.0048(12) 0.0036(15)
C8 0.0332(16) 0.069(2) 0.0340(16) 0.0006(15) 0.0031(13) 0.0016(16)
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
C7 N1 C1 123.9(3)
C7 N1 H1N 118.0
C1 N1 H1N 118.0
C2 C1 C6 120.3(3)
C2 C1 N1 119.2(3)
C6 C1 N1 120.5(3)
C1 C2 C3 119.6(3)
C1 C2 Cl1 120.3(2)
C3 C2 Cl1 120.1(3)
C4 C3 C2 120.0(3)
C4 C3 Cl2 119.4(3)
C2 C3 Cl2 120.6(3)
C3 C4 C5 120.1(3)
C3 C4 H4 119.9
C5 C4 H4 119.9
C4 C5 C6 120.8(4)
C4 C5 H5 119.6
C6 C5 H5 119.6
C1 C6 C5 119.1(3)
C1 C6 H6 120.5
C5 C6 H6 120.5
O1 C7 N1 125.2(3)
O1 C7 C8 120.4(3)
N1 C7 C8 114.4(3)
C7 C8 Cl4 110.8(2)
C7 C8 Cl3 107.4(2)
Cl4 C8 Cl3 109.98(19)
C7 C8 H8 109.5
Cl4 C8 H8 109.5
Cl3 C8 H8 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C2 1.726(3)
Cl2 C3 1.723(4)
Cl3 C8 1.761(4)
Cl4 C8 1.752(4)
O1 C7 1.216(4)
N1 C7 1.333(4)
N1 C1 1.426(4)
N1 H1N 0.8600
C1 C2 1.382(4)
C1 C6 1.382(5)
C2 C3 1.394(4)
C3 C4 1.369(5)
C4 C5 1.370(6)
C4 H4 0.9300
C5 C6 1.389(5)
C5 H5 0.9300
C6 H6 0.9300
C7 C8 1.523(4)
C8 H8 0.9800
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
N1 H1N O1 1_655 0.86 1.95 2.790(3) 166.7
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
C7 N1 C1 C2 131.1(3)
C7 N1 C1 C6 -50.7(5)
C6 C1 C2 C3 0.4(5)
N1 C1 C2 C3 178.6(3)
C6 C1 C2 Cl1 -180.0(3)
N1 C1 C2 Cl1 -1.8(4)
C1 C2 C3 C4 0.3(5)
Cl1 C2 C3 C4 -179.3(3)
C1 C2 C3 Cl2 179.9(2)
Cl1 C2 C3 Cl2 0.3(4)
C2 C3 C4 C5 -0.4(6)
Cl2 C3 C4 C5 180.0(3)
C3 C4 C5 C6 -0.1(6)
C2 C1 C6 C5 -0.9(5)
N1 C1 C6 C5 -179.1(3)
C4 C5 C6 C1 0.8(6)
C1 N1 C7 O1 -3.4(6)
C1 N1 C7 C8 175.7(3)
O1 C7 C8 Cl4 -42.7(4)
N1 C7 C8 Cl4 138.2(3)
O1 C7 C8 Cl3 77.5(4)
N1 C7 C8 Cl3 -101.6(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2008097
