#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/84/2218416.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_2218416
loop_
_publ_author_name
'Gowda, B. Thimme'
'Kožíšek, Jozef'
'Tokarčík, Miroslav'
'Fuess, Hartmut'
_publ_section_title
;
 2-Chloro-N-phenylacetamide
;
_journal_coeditor_code           HB2728
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o987
_journal_paper_doi               10.1107/S160053680801266X
_journal_volume                  64
_journal_year                    2008
_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         169.6
_chemical_name_systematic
;
2-Chloro-N-phenylacetamide
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 102.13(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.0623(15)
_cell_length_b                   18.361(6)
_cell_length_c                   9.115(2)
_cell_measurement_reflns_used    159
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      25.12
_cell_measurement_theta_min      4.9
_cell_volume                     828.3(4)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003) and WinGX
(Farrugia, 1999)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      297(2)
_diffrn_detector_area_resol_mean 10.4340
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       '4-circle kappa geometry goniometer'
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur System'
_diffrn_measurement_method       ω
_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  0.0459
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2388
_diffrn_reflns_theta_full        26
_diffrn_reflns_theta_max         26
_diffrn_reflns_theta_min         4.26
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.399
_exptl_absorpt_correction_T_max  0.938
_exptl_absorpt_correction_T_min  0.905
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
[CrysAlis RED (Oxford Diffraction, 2006), using a multifaceted crystal
model
based on expressions derived by Clark & Reid (1995)]
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.36
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.1
_refine_diff_density_min         -0.109
_refine_ls_abs_structure_details 'Flack (1983), 254 Friedel pairs'
_refine_ls_abs_structure_Flack   0.04(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     106
_refine_ls_number_reflns         1067
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.957
_refine_ls_R_factor_all          0.1496
_refine_ls_R_factor_gt           0.0361
_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
[exp(3.70(sinθ/λ)²)]/[σ²(Fo²)+(0.035P)²]
where P = 0.33333Fo² + 0.66667Fc²
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0661
_refine_ls_wR_factor_ref         0.0857
_reflns_number_gt                385
_reflns_number_total             1067
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2728.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_H-M      'C c'
_cod_database_code               2218416
_cod_database_fobs_code          2218416
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, 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 1.3492(4) 0.15000(9) 0.9151(2) 0.1082(7) Uani d . 1
C C1 1.0871(11) 0.1998(3) 0.8076(6) 0.0824(18) Uani d . 1
H H1A 1.1488 0.2215 0.7237 0.099 Uiso calc R 1
H H1B 0.939 0.1671 0.7672 0.099 Uiso calc R 1
C C2 0.9849(11) 0.2595(3) 0.8961(6) 0.0629(17) Uani d . 1
N N1 0.7939(8) 0.3008(2) 0.8086(4) 0.0642(13) Uani d . 1
H H1N 0.7565 0.2897 0.7149 0.077 Uiso calc R 1
O O1 1.0653(7) 0.26846(19) 1.0314(3) 0.0833(13) Uani d . 1
C C3 0.6481(10) 0.3597(3) 0.8507(6) 0.0517(13) Uani d . 1
C C4 0.7302(11) 0.3975(3) 0.9862(6) 0.0670(17) Uani d . 1
H H4 0.888 0.3845 1.0536 0.08 Uiso calc R 1
C C5 0.5727(15) 0.4542(3) 1.0177(7) 0.082(2) Uani d . 1
H H5 0.6222 0.478 1.1094 0.099 Uiso calc R 1
C C6 0.3490(16) 0.4762(3) 0.9197(10) 0.0824(18) Uani d . 1
H H6 0.2513 0.516 0.9428 0.099 Uiso calc R 1
C C7 0.2640(13) 0.4399(4) 0.7850(7) 0.082(2) Uani d . 1
H H7 0.1068 0.4538 0.7183 0.099 Uiso calc R 1
C C8 0.4153(10) 0.3835(4) 0.7525(6) 0.0676(16) Uani d . 1
H H8 0.3614 0.3598 0.6609 0.081 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 0.1120(13) 0.1207(13) 0.0829(10) 0.0402(13) -0.0004(9) 0.0083(13)
C1 0.079(4) 0.091(4) 0.067(4) 0.022(4) -0.006(3) 0.006(4)
C2 0.070(4) 0.071(4) 0.045(3) -0.003(3) 0.005(3) 0.004(4)
N1 0.066(3) 0.084(3) 0.035(3) 0.012(3) -0.006(2) 0.003(3)
O1 0.102(3) 0.097(3) 0.039(2) 0.010(2) -0.013(2) -0.005(2)
C3 0.051(4) 0.062(4) 0.041(3) -0.001(3) 0.008(3) 0.002(3)
C4 0.055(4) 0.084(4) 0.059(4) 0.005(4) 0.007(3) -0.004(3)
C5 0.083(5) 0.097(5) 0.073(5) -0.005(5) 0.029(4) -0.014(4)
C6 0.078(5) 0.071(4) 0.101(5) 0.002(5) 0.027(4) 0.005(5)
C7 0.066(5) 0.094(5) 0.081(5) 0.019(5) 0.005(4) 0.020(5)
C8 0.053(4) 0.090(5) 0.058(4) 0.003(3) 0.006(3) 0.014(3)
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 0 '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 0.006 '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
C2 C1 Cl1 112.8(4)
C2 C1 H1A 109
Cl1 C1 H1A 109
C2 C1 H1B 109
Cl1 C1 H1B 109
H1A C1 H1B 107.8
O1 C2 N1 124.3(6)
O1 C2 C1 123.7(6)
N1 C2 C1 112.0(5)
C2 N1 C3 128.5(5)
C2 N1 H1N 115.7
C3 N1 H1N 115.7
C8 C3 C4 117.8(5)
C8 C3 N1 119.2(5)
C4 C3 N1 123.0(5)
C5 C4 C3 118.7(6)
C5 C4 H4 120.7
C3 C4 H4 120.7
C6 C5 C4 122.0(6)
C6 C5 H5 119
C4 C5 H5 119
C5 C6 C7 120.3(6)
C5 C6 H6 119.8
C7 C6 H6 119.8
C8 C7 C6 118.5(6)
C8 C7 H7 120.8
C6 C7 H7 120.8
C7 C8 C3 122.6(6)
C7 C8 H8 118.7
C3 C8 H8 118.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.735(5)
C1 C2 1.515(6)
C1 H1A 0.97
C1 H1B 0.97
C2 O1 1.226(6)
C2 N1 1.350(6)
N1 C3 1.407(6)
N1 H1N 0.86
C3 C8 1.392(6)
C3 C4 1.401(7)
C4 C5 1.378(7)
C4 H4 0.93
C5 C6 1.349(8)
C5 H5 0.93
C6 C7 1.384(9)
C6 H6 0.93
C7 C8 1.357(7)
C7 H7 0.93
C8 H8 0.93
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 4_454 0.86 2.05 2.848(5) 155
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
Cl1 C1 C2 O1 -4.8(7)
Cl1 C1 C2 N1 175.8(4)
O1 C2 N1 C3 -1.1(9)
C1 C2 N1 C3 178.3(5)
C2 N1 C3 C8 -164.2(5)
C2 N1 C3 C4 17.8(8)
C8 C3 C4 C5 2.3(8)
N1 C3 C4 C5 -179.6(5)
C3 C4 C5 C6 -2.8(9)
C4 C5 C6 C7 2.7(9)
C5 C6 C7 C8 -2.0(9)
C6 C7 C8 C3 1.7(8)
C4 C3 C8 C7 -1.8(8)
N1 C3 C8 C7 -180.0(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 11001
