#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:31:46 +0200 (vie 13 de oct de 2017) $
#$Revision: 201979 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/26/2232628.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_2232628
loop_
_publ_author_name
'Ma, Dong-Sheng'
'Liu, Pei-Jiang'
'Zhang, Shuai'
'Hou, Guang-Feng'
_publ_section_title
;
 2-(4-Chlorophenyl)acetamide
;
_journal_coeditor_code           CV5191
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3261
_journal_paper_doi               10.1107/S1600536811046836
_journal_volume                  67
_journal_year                    2011
_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_systematic
;
2-(4-Chlorophenyl)acetamide
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.917(2)
_cell_length_b                   6.033(4)
_cell_length_c                   26.680(12)
_cell_measurement_reflns_used    5994
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      3.05
_cell_volume                     791.4(7)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            7733
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         3.05
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.418
_exptl_absorpt_correction_T_max  0.9697
_exptl_absorpt_correction_T_min  0.8873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.173
_refine_ls_abs_structure_details 'Flack (1983), 704 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.12(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     108
_refine_ls_number_reflns         1807
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0366
_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)+(0.0360P)²+0.1017P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0830
_reflns_number_gt                1451
_reflns_number_total             1807
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cv5191.cif
_cod_data_source_block           I
_cod_original_cell_volume        791.5(7)
_cod_database_code               2232628
_cod_database_fobs_code          2232628
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'
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_symmetry_multiplicity
C C1 0.3632(4) 0.5073(3) 0.79843(7) 0.0335(4) Uani d . 1 1
C C2 0.2527(4) 0.3677(5) 0.84087(10) 0.0603(7) Uani d . 1 1
H H2A 0.1560 0.4638 0.8639 0.072 Uiso calc R 1 1
H H2B 0.1222 0.2633 0.8272 0.072 Uiso calc R 1 1
C C3 0.4640(4) 0.2408(4) 0.86973(8) 0.0429(5) Uani d . 1 1
C C4 0.5575(5) 0.0374(4) 0.85279(8) 0.0487(6) Uani d . 1 1
H H4 0.4907 -0.0195 0.8228 0.058 Uiso calc R 1 1
C C5 0.7475(5) -0.0822(3) 0.87944(8) 0.0451(5) Uani d . 1 1
H H5 0.8079 -0.2185 0.8676 0.054 Uiso calc R 1 1
C C6 0.8470(4) 0.0017(4) 0.92375(8) 0.0410(5) Uani d . 1 1
C C7 0.7620(5) 0.2049(4) 0.94146(8) 0.0472(6) Uani d . 1 1
H H7 0.8324 0.2622 0.9711 0.057 Uiso calc R 1 1
C C8 0.5697(5) 0.3221(4) 0.91430(8) 0.0487(5) Uani d . 1 1
H H8 0.5100 0.4586 0.9262 0.058 Uiso calc R 1 1
Cl Cl1 1.08553(13) -0.14906(11) 0.95804(2) 0.0605(2) Uani d . 1 1
N N1 0.1788(3) 0.6234(4) 0.77353(7) 0.0441(4) Uani d D 1 1
H H11 0.004(2) 0.613(4) 0.7811(8) 0.046(6) Uiso d D 1 1
H H12 0.225(5) 0.714(4) 0.7485(7) 0.064(8) Uiso d D 1 1
O O1 0.6073(3) 0.5149(3) 0.78808(5) 0.0435(4) Uani d . 1 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 0.0263(9) 0.0376(11) 0.0367(10) -0.0005(9) 0.0007(8) -0.0027(8)
C2 0.0291(11) 0.0819(19) 0.0699(15) 0.0050(12) 0.0050(11) 0.0347(15)
C3 0.0310(11) 0.0528(13) 0.0449(11) 0.0000(9) 0.0035(9) 0.0145(9)
C4 0.0493(13) 0.0554(14) 0.0416(11) -0.0093(12) -0.0077(11) -0.0001(10)
C5 0.0511(13) 0.0368(12) 0.0475(12) 0.0016(9) 0.0072(11) -0.0041(9)
C6 0.0381(11) 0.0444(12) 0.0406(10) 0.0018(10) 0.0046(9) 0.0071(9)
C7 0.0514(13) 0.0514(14) 0.0387(11) 0.0009(10) -0.0027(10) -0.0056(10)
C8 0.0503(13) 0.0433(13) 0.0525(12) 0.0118(12) 0.0069(12) -0.0003(10)
Cl1 0.0520(3) 0.0695(4) 0.0598(3) 0.0147(3) -0.0015(3) 0.0194(3)
N1 0.0243(8) 0.0587(12) 0.0494(10) -0.0006(8) 0.0013(8) 0.0149(10)
O1 0.0237(6) 0.0529(9) 0.0538(8) -0.0038(7) 0.0051(7) 0.0046(7)
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
O1 C1 N1 122.34(19)
O1 C1 C2 122.57(18)
N1 C1 C2 115.08(17)
C3 C2 C1 114.78(17)
C3 C2 H2A 108.6
C1 C2 H2A 108.6
C3 C2 H2B 108.6
C1 C2 H2B 108.6
H2A C2 H2B 107.5
C4 C3 C8 117.9(2)
C4 C3 C2 120.9(2)
C8 C3 C2 121.2(2)
C5 C4 C3 121.3(2)
C5 C4 H4 119.3
C3 C4 H4 119.3
C6 C5 C4 119.5(2)
C6 C5 H5 120.3
C4 C5 H5 120.3
C5 C6 C7 120.9(2)
C5 C6 Cl1 119.88(18)
C7 C6 Cl1 119.21(17)
C6 C7 C8 118.8(2)
C6 C7 H7 120.6
C8 C7 H7 120.6
C7 C8 C3 121.6(2)
C7 C8 H8 119.2
C3 C8 H8 119.2
C1 N1 H11 120.9(16)
C1 N1 H12 121.7(18)
H11 N1 H12 117(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.232(2)
C1 N1 1.324(3)
C1 C2 1.512(3)
C2 C3 1.503(3)
C2 H2A 0.9700
C2 H2B 0.9700
C3 C4 1.386(3)
C3 C8 1.387(3)
C4 C5 1.378(3)
C4 H4 0.9300
C5 C6 1.376(3)
C5 H5 0.9300
C6 C7 1.379(3)
C6 Cl1 1.744(2)
C7 C8 1.386(3)
C7 H7 0.9300
C8 H8 0.9300
N1 H11 0.883(10)
N1 H12 0.892(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
N1 H11 O1 1_455 0.883(10) 2.049(11) 2.911(2) 165(2)
N1 H12 O1 3_656 0.892(10) 2.221(14) 3.064(3) 157(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 558441
