#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/34/2213415.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_2213415
loop_
_publ_author_name
'B. Thimme Gowda'
'Sabine Foro'
'Hartmut Fuess '
_publ_section_title
;
 N-(2,3-Dichlorophenyl)acetamide
;
_journal_coeditor_code           IM2006
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2631
_journal_page_last               o2632
_journal_paper_doi               10.1107/S1600536807019307
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C8 H7 Cl2 N O'
_chemical_formula_moiety         'C8 H7 Cl2 N O'
_chemical_formula_sum            'C8 H7 Cl2 N O'
_chemical_formula_weight         204.05
_chemical_name_systematic
;
N-(2,3-dichlorophenyl)acetamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 98.915(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.7524(5)
_cell_length_b                   12.2460(10)
_cell_length_c                   15.1400(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      24.26
_cell_measurement_theta_min      4.66
_cell_volume                     870.47(13)
_computing_cell_refinement       CAD-4-PC
_computing_data_collection       'CAD-4-PC (Enraf--Nonius, 1996)'
_computing_data_reduction        'REDU4 (Stoe & Cie, 1987)'
_computing_molecular_graphics
;
PLATON (Spek, 2003) and ORTEP-3 (Farrugia, 1997)
;
_computing_publication_material  SHELXL97
_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  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0554
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            1923
_diffrn_reflns_theta_full        66.93
_diffrn_reflns_theta_max         66.93
_diffrn_reflns_theta_min         4.67
_diffrn_standards_decay_%        4.3
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    6.287
_exptl_absorpt_correction_T_max  0.6274
_exptl_absorpt_correction_T_min  0.4847
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.238
_refine_ls_extinction_coef       0.0062(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1560
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0415P)²+0.0972P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.1024
_reflns_number_gt                1072
_reflns_number_total             1560
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            im2006.cif
_cod_data_source_block           I
_cod_original_cell_volume        870.50(10)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2213415
_cod_database_fobs_code          2213415
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C C1 0.0128(7) -0.3229(3) -0.0294(2) 0.0495(9) Uani d . 1
H H1A -0.0168 -0.3908 -0.0006 0.059 Uiso calc R 1
H H1B 0.2123 -0.3134 -0.0312 0.059 Uiso calc R 1
H H1C -0.0898 -0.3236 -0.0893 0.059 Uiso calc R 1
C C2 -0.0917(7) -0.2313(3) 0.0215(2) 0.0404(8) Uani d . 1
C C5 0.0701(6) -0.0852(3) 0.1298(2) 0.0359(7) Uani d . 1
C C6 0.2434(6) -0.0729(3) 0.2121(2) 0.0358(7) Uani d . 1
C C7 0.2093(8) 0.0171(3) 0.2651(2) 0.0425(8) Uani d . 1
C C8 0.0025(8) 0.0941(3) 0.2378(2) 0.0510(9) Uani d . 1
H H8 -0.0199 0.1542 0.2737 0.061 Uiso calc R 1
C C9 -0.1704(8) 0.0808(3) 0.1567(3) 0.0523(9) Uani d . 1
H H9 -0.3120 0.1319 0.1382 0.063 Uiso calc R 1
C C10 -0.1366(7) -0.0070(3) 0.1027(2) 0.0443(8) Uani d . 1
H H10 -0.2532 -0.0141 0.0477 0.053 Uiso calc R 1
N N4 0.1139(5) -0.1758(2) 0.07566(18) 0.0389(6) Uani d D 1
H H4N 0.286(3) -0.197(3) 0.079(2) 0.047 Uiso d D 1
O O3 -0.3435(5) -0.2085(2) 0.01501(18) 0.0601(8) Uani d . 1
Cl Cl11 0.49749(19) -0.17057(7) 0.24850(6) 0.0466(3) Uani d . 1
Cl Cl12 0.4238(2) 0.03476(8) 0.36764(6) 0.0625(3) Uani d . 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
C1 0.0390(19) 0.055(2) 0.053(2) -0.0027(18) 0.0024(16) -0.0118(18)
C2 0.0310(17) 0.048(2) 0.0413(18) -0.0029(15) 0.0018(14) 0.0052(15)
C5 0.0319(16) 0.0365(16) 0.0401(16) -0.0003(15) 0.0074(13) 0.0003(15)
C6 0.0311(16) 0.0354(17) 0.0416(17) -0.0012(14) 0.0081(13) 0.0036(14)
C7 0.0440(19) 0.043(2) 0.0417(18) -0.0076(16) 0.0102(15) -0.0009(15)
C8 0.055(2) 0.041(2) 0.061(2) 0.0029(19) 0.0212(18) -0.0035(17)
C9 0.047(2) 0.044(2) 0.069(2) 0.0127(18) 0.0208(18) 0.0090(19)
C10 0.0368(19) 0.051(2) 0.0444(18) 0.0086(16) 0.0054(15) 0.0074(16)
N4 0.0231(13) 0.0485(16) 0.0432(15) 0.0051(13) -0.0008(11) -0.0042(13)
O3 0.0255(13) 0.0772(19) 0.0760(19) -0.0016(12) 0.0026(12) -0.0145(15)
Cl11 0.0419(4) 0.0454(4) 0.0487(5) 0.0050(4) -0.0052(3) 0.0029(4)
Cl12 0.0705(7) 0.0662(6) 0.0486(5) -0.0100(5) 0.0022(4) -0.0136(5)
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'
O O 0.0492 0.0322 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
O3 C2 N4 122.7(3)
O3 C2 C1 122.2(3)
N4 C2 C1 115.0(3)
C10 C5 C6 119.0(3)
C10 C5 N4 122.1(3)
C6 C5 N4 119.0(3)
C7 C6 C5 119.9(3)
C7 C6 Cl11 120.3(3)
C5 C6 Cl11 119.9(2)
C8 C7 C6 120.8(3)
C8 C7 Cl12 118.4(3)
C6 C7 Cl12 120.8(3)
C9 C8 C7 119.0(3)
C9 C8 H8 120.5
C7 C8 H8 120.5
C10 C9 C8 120.9(3)
C10 C9 H9 119.5
C8 C9 H9 119.5
C9 C10 C5 120.4(3)
C9 C10 H10 119.8
C5 C10 H10 119.8
C2 N4 C5 125.9(3)
C2 N4 H4N 119(2)
C5 N4 H4N 115(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.490(5)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 O3 1.217(4)
C2 N4 1.357(4)
C5 C10 1.387(4)
C5 C6 1.391(4)
C5 N4 1.414(4)
C6 C7 1.387(4)
C6 Cl11 1.728(3)
C7 C8 1.379(5)
C7 Cl12 1.734(3)
C8 C9 1.377(5)
C8 H8 0.9300
C9 C10 1.376(5)
C9 H9 0.9300
C10 H10 0.9300
N4 H4N 0.850(10)
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
N4 H4N Cl11 . 0.850(10) 2.63(3) 2.949(3) 104(2)
N4 H4N O3 1_655 0.850(10) 2.14(2) 2.896(4) 148(3)
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
C10 C5 C6 C7 -0.7(5)
N4 C5 C6 C7 178.1(3)
C10 C5 C6 Cl11 178.6(2)
N4 C5 C6 Cl11 -2.6(4)
C5 C6 C7 C8 1.0(5)
Cl11 C6 C7 C8 -178.3(3)
C5 C6 C7 Cl12 -179.6(2)
Cl11 C6 C7 Cl12 1.1(4)
C6 C7 C8 C9 -0.2(5)
Cl12 C7 C8 C9 -179.6(3)
C7 C8 C9 C10 -0.8(6)
C8 C9 C10 C5 1.1(5)
C6 C5 C10 C9 -0.3(5)
N4 C5 C10 C9 -179.1(3)
O3 C2 N4 C5 -1.1(5)
C1 C2 N4 C5 179.2(3)
C10 C5 N4 C2 -36.0(5)
C6 C5 N4 C2 145.3(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 216327
