#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/50/2205092.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_2205092
loop_
_publ_author_name
'Tai, Xi-Shi'
'Liu, Wan-Yi'
'Liu, Yan-Zhen'
'Li, Yi-Zhi'
_publ_section_title
;
 2-Acetyl-3'-chloroacetanilide
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o389
_journal_page_last               o390
_journal_paper_doi               10.1107/S1600536805001145
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C10 H10 Cl N O2'
_chemical_formula_moiety         'C10 H10 Cl N O2'
_chemical_formula_sum            'C10 H10 Cl N O2'
_chemical_formula_weight         211.64
_chemical_name_common            2-Acetyl-3'-chloroacetanilide
_chemical_name_systematic
;
N-(3-chlorophenyl)-3-oxobutanamide
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.5485(16)
_cell_length_b                   8.2197(13)
_cell_length_c                   25.940(4)
_cell_measurement_reflns_used    702
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.27
_cell_measurement_theta_min      2.64
_cell_volume                     2035.9(6)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_sigmaI/netI    0.0476
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            10164
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.65
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       plate
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.136
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1988
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0413
_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)+(0.03P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0678
_refine_ls_wR_factor_ref         0.0748
_reflns_number_gt                1285
_reflns_number_total             1988
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is6034.cif
_cod_data_source_block           I
_cod_database_code               2205092
_cod_database_fobs_code          2205092
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_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_type_symbol
Cl1 0.58989(7) 0.23432(7) 0.52633(2) 0.0703(2) Uani d . 1 Cl
N1 0.42667(13) 0.25024(16) 0.71108(5) 0.0385(3) Uani d . 1 N
H1 0.5134 0.2364 0.7189 0.046 Uiso calc R 1 H
O1 0.20787(11) 0.24572(17) 0.74412(5) 0.0572(4) Uani d . 1 O
O2 0.36625(18) 0.42013(18) 0.83242(6) 0.0734(5) Uani d . 1 O
C1 0.39771(17) 0.29927(19) 0.66060(7) 0.0339(4) Uani d . 1 C
C2 0.49338(19) 0.2525(2) 0.62307(7) 0.0410(4) Uani d . 1 C
H2 0.5719 0.1920 0.6320 0.049 Uiso calc R 1 H
C3 0.4714(2) 0.2960(2) 0.57296(7) 0.0445(5) Uani d . 1 C
C4 0.3579(2) 0.3849(2) 0.55802(8) 0.0552(5) Uani d . 1 C
H4 0.3438 0.4135 0.5237 0.066 Uiso calc R 1 H
C5 0.2656(2) 0.4300(3) 0.59573(9) 0.0561(6) Uani d . 1 C
H5 0.1875 0.4912 0.5866 0.067 Uiso calc R 1 H
C6 0.28399(19) 0.3882(2) 0.64642(7) 0.0481(5) Uani d . 1 C
H6 0.2189 0.4206 0.6710 0.058 Uiso calc R 1 H
C7 0.33240(17) 0.2223(2) 0.74891(7) 0.0361(4) Uani d . 1 C
C8 0.39229(17) 0.1587(2) 0.79803(7) 0.0387(4) Uani d . 1 C
H8A 0.4885 0.1256 0.7921 0.046 Uiso calc R 1 H
H8B 0.3399 0.0632 0.8085 0.046 Uiso calc R 1 H
C9 0.38898(19) 0.2817(3) 0.84083(8) 0.0499(5) Uani d . 1 C
C10 0.4198(3) 0.2174(3) 0.89323(9) 0.0753(7) Uani d . 1 C
H10A 0.4216 0.3057 0.9175 0.113 Uiso calc R 1 H
H10B 0.5092 0.1640 0.8930 0.113 Uiso calc R 1 H
H10C 0.3485 0.1411 0.9030 0.113 Uiso calc R 1 H
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 0.0908(4) 0.0710(4) 0.0491(3) 0.0327(3) 0.0127(3) 0.0063(3)
N1 0.0163(6) 0.0550(9) 0.0442(8) -0.0007(7) 0.0000(6) 0.0040(7)
O1 0.0204(7) 0.0863(12) 0.0650(9) 0.0015(7) 0.0033(6) 0.0052(8)
O2 0.0871(12) 0.0517(9) 0.0814(10) 0.0124(8) -0.0154(10) -0.0107(8)
C1 0.0261(8) 0.0312(9) 0.0444(10) -0.0028(7) -0.0063(8) -0.0013(7)
C2 0.0264(9) 0.0473(11) 0.0492(10) -0.0041(8) 0.0019(7) 0.0014(9)
C3 0.0429(11) 0.0485(10) 0.0420(12) -0.0009(9) 0.0006(8) -0.0003(9)
C4 0.0573(13) 0.0587(13) 0.0497(12) -0.0054(11) -0.0189(11) 0.0073(10)
C5 0.0462(12) 0.0575(14) 0.0645(14) 0.0161(9) -0.0183(11) 0.0032(10)
C6 0.0367(11) 0.0554(12) 0.0523(12) 0.0097(9) -0.0101(9) -0.0048(10)
C7 0.0267(9) 0.0366(9) 0.0450(10) 0.0019(7) 0.0022(7) -0.0050(8)
C8 0.0266(8) 0.0406(10) 0.0489(11) 0.0005(7) 0.0033(8) 0.0102(7)
C9 0.0366(10) 0.0527(13) 0.0605(12) 0.0069(10) -0.0064(9) 0.0054(9)
C10 0.0644(15) 0.1007(19) 0.0609(15) 0.0202(15) -0.0061(12) 0.0081(13)
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
C7 N1 C1 126.69(14)
C7 N1 H1 116.7
C1 N1 H1 116.7
C6 C1 C2 118.95(17)
C6 C1 N1 124.51(16)
C2 C1 N1 116.54(15)
C3 C2 C1 119.61(17)
C3 C2 H2 120.2
C1 C2 H2 120.2
C4 C3 C2 122.25(18)
C4 C3 Cl1 118.53(15)
C2 C3 Cl1 119.22(14)
C3 C4 C5 117.01(19)
C3 C4 H4 121.5
C5 C4 H4 121.5
C4 C5 C6 122.40(18)
C4 C5 H5 118.8
C6 C5 H5 118.8
C1 C6 C5 119.78(18)
C1 C6 H6 120.1
C5 C6 H6 120.1
O1 C7 N1 123.56(17)
O1 C7 C8 121.33(17)
N1 C7 C8 115.11(14)
C7 C8 C9 112.82(15)
C7 C8 H8A 109.0
C9 C8 H8A 109.0
C7 C8 H8B 109.0
C9 C8 H8B 109.0
H8A C8 H8B 107.8
O2 C9 C10 123.3(2)
O2 C9 C8 121.10(18)
C10 C9 C8 115.62(19)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C3 1.7322(19)
N1 C7 1.351(2)
N1 C1 1.398(2)
N1 H1 0.8600
O1 C7 1.2108(19)
O2 C9 1.179(2)
C1 C6 1.360(2)
C1 C2 1.389(2)
C2 C3 1.364(3)
C2 H2 0.9300
C3 C4 1.363(3)
C4 C5 1.368(3)
C4 H4 0.9300
C5 C6 1.370(3)
C5 H5 0.9300
C6 H6 0.9300
C7 C8 1.491(2)
C8 C9 1.502(3)
C8 H8A 0.9700
C8 H8B 0.9700
C9 C10 1.488(3)
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
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 6_657 0.86 2.09 2.9259(18) 163
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 68016
