#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/40/2214092.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_2214092
loop_
_publ_author_name
'B. Thimme Gowda'
'Ingrid Svoboda'
'Hartmut Fuess '
_publ_section_title
;
 N-(2-Chlorophenyl)acetamide
;
_journal_coeditor_code           BT2391
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3267
_journal_page_last               o3267
_journal_paper_doi               10.1107/S1600536807028991
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C8 H8 Cl N O'
_chemical_formula_moiety         'C8 H8 Cl N O'
_chemical_formula_sum            'C8 H8 Cl N O'
_chemical_formula_weight         169.60
_chemical_name_common            2-Chloroacetanilide
_chemical_name_systematic
;
N-(2-Chlorophenyl)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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.74(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.7468(4)
_cell_length_b                   11.6990(10)
_cell_length_c                   14.640(2)
_cell_measurement_reflns_used    1844
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.990
_cell_measurement_theta_min      2.252
_cell_volume                     808.92(15)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2006)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2006)
;
_computing_data_reduction
;
CrysAlis RED
;
_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      100(2)
_diffrn_detector_area_resol_mean 8.4012
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
;
_diffrn_measurement_method
;
Rotation method data acquisition using ω and φ
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0419
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5681
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.80
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.409
_exptl_absorpt_correction_T_max  0.9838
_exptl_absorpt_correction_T_min  0.8535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2006) using a multifaceted crystal
model (Clark & Reid, 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.227
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     116
_refine_ls_number_reflns         1641
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0321
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0443P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0807
_reflns_number_gt                1204
_reflns_number_total             1641
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2391.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_Hall     -P2yn
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2214092
_cod_database_fobs_code          2214092
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
C C1 -0.0446(3) 0.05702(15) 0.35962(11) 0.0146(4) Uani d . 1
C C2 0.0451(4) 0.01850(15) 0.27730(12) 0.0166(4) Uani d . 1
C C3 -0.0388(4) -0.08698(16) 0.24092(13) 0.0200(4) Uani d . 1
H H3 0.031(4) -0.1113(15) 0.1851(13) 0.024 Uiso d . 1
C C4 -0.2228(4) -0.15359(16) 0.28474(13) 0.0216(4) Uani d . 1
H H4 -0.278(4) -0.2266(17) 0.2550(13) 0.026 Uiso d . 1
C C5 -0.3189(4) -0.11594(16) 0.36608(13) 0.0206(4) Uani d . 1
H H5 -0.448(4) -0.1583(16) 0.3943(12) 0.025 Uiso d . 1
C C6 -0.2289(4) -0.01185(16) 0.40335(13) 0.0166(4) Uani d . 1
H H6 -0.288(4) 0.0123(15) 0.4588(13) 0.020 Uiso d . 1
C C7 -0.1093(4) 0.23926(15) 0.43748(12) 0.0158(4) Uani d . 1
C C8 0.0367(4) 0.34568(15) 0.47456(13) 0.0219(4) Uani d . 1
H H8A -0.0056 0.4087 0.4313 0.026 Uiso calc R 1
H H8B 0.2417 0.3327 0.4828 0.026 Uiso calc R 1
H H8C -0.0305 0.3651 0.5338 0.026 Uiso calc R 1
N N1 0.0540(3) 0.16230(13) 0.39826(10) 0.0142(3) Uani d . 1
H H1 0.221(4) 0.1778(16) 0.3978(12) 0.017 Uiso d . 1
O O1 -0.3652(2) 0.22592(11) 0.44072(9) 0.0223(3) Uani d . 1
Cl Cl1 0.27008(9) 0.10385(4) 0.21925(3) 0.02233(16) 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 0.0125(9) 0.0149(9) 0.0157(9) 0.0015(8) -0.0020(7) 0.0011(8)
C2 0.0135(9) 0.0195(10) 0.0172(9) 0.0006(8) 0.0039(7) 0.0035(8)
C3 0.0178(9) 0.0221(11) 0.0197(10) 0.0027(8) 0.0005(8) -0.0041(9)
C4 0.0209(10) 0.0149(10) 0.0279(10) -0.0010(8) -0.0036(9) -0.0036(9)
C5 0.0189(9) 0.0201(11) 0.0226(10) -0.0050(8) 0.0007(8) 0.0050(9)
C6 0.0171(10) 0.0186(10) 0.0140(9) 0.0004(8) 0.0015(8) 0.0015(8)
C7 0.0142(9) 0.0185(10) 0.0146(9) 0.0004(8) 0.0009(7) 0.0019(8)
C8 0.0214(10) 0.0194(10) 0.0253(10) 0.0030(8) 0.0049(8) -0.0035(9)
N1 0.0083(7) 0.0152(8) 0.0193(8) -0.0033(7) 0.0021(6) -0.0006(7)
O1 0.0124(7) 0.0248(7) 0.0302(8) -0.0008(6) 0.0039(6) -0.0035(6)
Cl1 0.0220(3) 0.0250(3) 0.0214(2) -0.0030(2) 0.00937(18) -0.0004(2)
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'
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'
Cl Cl 0.1484 0.1585 '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
C6 C1 C2 118.13(16)
C6 C1 N1 121.20(15)
C2 C1 N1 120.65(15)
C3 C2 C1 121.30(17)
C3 C2 Cl1 119.26(14)
C1 C2 Cl1 119.45(14)
C4 C3 C2 119.75(18)
C4 C3 H3 121.3(11)
C2 C3 H3 118.9(11)
C3 C4 C5 119.88(18)
C3 C4 H4 116.1(11)
C5 C4 H4 124.0(11)
C6 C5 C4 120.14(18)
C6 C5 H5 119.4(11)
C4 C5 H5 120.4(11)
C5 C6 C1 120.76(17)
C5 C6 H6 120.3(11)
C1 C6 H6 119.0(11)
O1 C7 N1 122.80(16)
O1 C7 C8 120.91(16)
N1 C7 C8 116.25(15)
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C7 N1 C1 124.61(14)
C7 N1 H1 117.0(13)
C1 N1 H1 118.3(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.391(2)
C1 C2 1.393(2)
C1 N1 1.415(2)
C2 C3 1.387(3)
C2 Cl1 1.7440(18)
C3 C4 1.376(3)
C3 H3 0.955(19)
C4 C5 1.389(3)
C4 H4 0.983(19)
C5 C6 1.384(3)
C5 H5 0.918(18)
C6 H6 0.928(18)
C7 O1 1.2305(19)
C7 N1 1.353(2)
C7 C8 1.500(2)
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
N1 H1 0.813(18)
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 H1 O1 1_655 0.813(18) 2.079(18) 2.8630(19) 161.7(17)
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
C6 C1 C2 C3 -2.0(3)
N1 C1 C2 C3 176.81(15)
C6 C1 C2 Cl1 178.65(13)
N1 C1 C2 Cl1 -2.6(2)
C1 C2 C3 C4 2.5(3)
Cl1 C2 C3 C4 -178.12(14)
C2 C3 C4 C5 -1.3(3)
C3 C4 C5 C6 -0.3(3)
C4 C5 C6 C1 0.8(3)
C2 C1 C6 C5 0.3(3)
N1 C1 C6 C5 -178.47(15)
O1 C7 N1 C1 -2.3(3)
C8 C7 N1 C1 179.90(15)
C6 C1 N1 C7 -42.7(2)
C2 C1 N1 C7 138.56(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10322
