#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/18/2221835.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_2221835
loop_
_publ_author_name
'Gowda, B. Thimme'
'Foro, Sabine'
'Terao, Hiromitsu'
'Fuess, Hartmut'
_publ_section_title
;
 N-(3-Bromophenyl)acetamide
;
_journal_coeditor_code           TK2417
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1039
_journal_paper_doi               10.1107/S1600536809013294
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C8 H8 Br N O'
_chemical_formula_moiety         'C8 H8 Br N O'
_chemical_formula_sum            'C8 H8 Br N O'
_chemical_formula_weight         214.06
_chemical_name_systematic
;
N-(3-Bromophenyl)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
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   4.7836(6)
_cell_length_b                   18.7650(10)
_cell_length_c                   19.379(2)
_cell_measurement_reflns_used    3601
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      2.4
_cell_volume                     1739.5(3)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2007)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2004)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2007)
;
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_av_sigmaI/netI    0.053
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9612
_diffrn_reflns_theta_full        26.4
_diffrn_reflns_theta_max         26.4
_diffrn_reflns_theta_min         2.4
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    4.667
_exptl_absorpt_correction_T_max  0.685
_exptl_absorpt_correction_T_min  0.226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'long needle'
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.49
_refine_ls_abs_structure_details 'Flack (1983), 1366 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.008(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.99
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3449
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.99
_refine_ls_R_factor_all          0.094
_refine_ls_R_factor_gt           0.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0455P)²+0.0252P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.082
_refine_ls_wR_factor_ref         0.093
_reflns_number_gt                2043
_reflns_number_total             3449
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2417.cif
_cod_data_source_block           I
_cod_database_code               2221835
_cod_database_fobs_code          2221835
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.64658(17) 0.36438(3) 0.40336(3) 0.0961(3) Uani d . 1 . .
O O1 1.0611(8) 0.22271(18) 0.20168(19) 0.0786(12) Uani d . 1 . .
N N1 0.9531(7) 0.13129(19) 0.27225(19) 0.0531(10) Uani d . 1 . .
H H1N 0.9782 0.0863 0.2779 0.064 Uiso calc R 1 . .
C C1 0.7804(10) 0.1647(2) 0.3206(2) 0.0492(12) Uani d . 1 . .
C C2 0.7903(10) 0.2377(2) 0.3338(2) 0.0524(12) Uani d . 1 . .
H H2 0.9111 0.2670 0.3092 0.063 Uiso calc R 1 . .
C C3 0.6192(12) 0.2656(3) 0.3838(2) 0.0606(14) Uani d . 1 . .
C C4 0.4398(12) 0.2247(4) 0.4216(3) 0.0740(17) Uani d . 1 . .
H H4 0.3269 0.2450 0.4553 0.089 Uiso calc R 1 . .
C C5 0.4300(12) 0.1519(3) 0.4084(3) 0.0848(18) Uani d . 1 . .
H H5 0.3068 0.1234 0.4331 0.102 Uiso calc R 1 . .
C C6 0.6000(11) 0.1215(3) 0.3592(3) 0.0691(15) Uani d . 1 . .
H H6 0.5951 0.0726 0.3516 0.083 Uiso calc R 1 . .
C C7 1.0850(10) 0.1608(3) 0.2180(2) 0.0546(13) Uani d . 1 . .
C C8 1.2664(11) 0.1102(2) 0.1767(2) 0.0726(17) Uani d . 1 . .
H H8A 1.2240 0.0620 0.1895 0.087 Uiso calc R 1 . .
H H8B 1.4597 0.1199 0.1861 0.087 Uiso calc R 1 . .
H H8C 1.2303 0.1166 0.1284 0.087 Uiso calc R 1 . .
Br Br2 0.30944(16) 0.49664(3) -0.03009(3) 0.0919(3) Uani d . 1 . .
O O2 0.9050(8) 0.48750(17) 0.18809(18) 0.0709(10) Uani d . 1 . .
N N2 0.8933(8) 0.36972(18) 0.16644(18) 0.0475(9) Uani d . 1 . .
H H2N 0.9634 0.3294 0.1785 0.057 Uiso calc R 1 . .
C C9 0.6865(9) 0.3675(2) 0.11456(19) 0.0397(10) Uani d . 1 . .
C C10 0.6162(10) 0.4252(2) 0.0737(2) 0.0464(11) Uani d . 1 . .
H H10 0.7039 0.4690 0.0799 0.056 Uiso calc R 1 . .
C C11 0.4147(10) 0.4168(2) 0.0239(2) 0.0499(12) Uani d . 1 . .
C C12 0.2819(9) 0.3533(3) 0.0127(2) 0.0528(12) Uani d . 1 . .
H H12 0.1476 0.3489 -0.0218 0.063 Uiso calc R 1 . .
C C13 0.3519(12) 0.2959(3) 0.0536(2) 0.0576(13) Uani d . 1 . .
H H13 0.2619 0.2525 0.0473 0.069 Uiso calc R 1 . .
C C14 0.5532(9) 0.3025(2) 0.1035(2) 0.0490(12) Uani d . 1 . .
H H14 0.6013 0.2632 0.1302 0.059 Uiso calc R 1 . .
C C15 0.9939(9) 0.4277(3) 0.1993(2) 0.0490(12) Uani d . 1 . .
C C16 1.2135(10) 0.4133(3) 0.2521(3) 0.0652(14) Uani d . 1 . .
H H16A 1.2663 0.3640 0.2502 0.078 Uiso calc R 1 . .
H H16B 1.1416 0.4242 0.2971 0.078 Uiso calc R 1 . .
H H16C 1.3739 0.4426 0.2429 0.078 Uiso calc R 1 . .
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'
Br Br -0.2901 2.4595 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 N1 C1 . . 128.1(4) ?
C7 N1 H1N . . 116.0 ?
C1 N1 H1N . . 116.0 ?
C2 C1 N1 . . 123.0(4) ?
C2 C1 C6 . . 119.5(5) ?
N1 C1 C6 . . 117.5(4) ?
C3 C2 C1 . . 119.0(5) ?
C3 C2 H2 . . 120.5 ?
C1 C2 H2 . . 120.5 ?
C4 C3 C2 . . 122.7(5) ?
C4 C3 Br1 . . 119.1(4) ?
C2 C3 Br1 . . 118.2(4) ?
C3 C4 C5 . . 118.3(5) ?
C3 C4 H4 . . 120.8 ?
C5 C4 H4 . . 120.8 ?
C6 C5 C4 . . 121.0(5) ?
C6 C5 H5 . . 119.5 ?
C4 C5 H5 . . 119.5 ?
C5 C6 C1 . . 119.6(5) ?
C5 C6 H6 . . 120.2 ?
C1 C6 H6 . . 120.2 ?
O1 C7 N1 . . 123.7(4) ?
O1 C7 C8 . . 121.3(4) ?
N1 C7 C8 . . 115.0(4) ?
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 ?
C15 N2 C9 . . 127.6(4) ?
C15 N2 H2N . . 116.2 ?
C9 N2 H2N . . 116.2 ?
C10 C9 C14 . . 119.1(4) ?
C10 C9 N2 . . 123.7(4) ?
C14 C9 N2 . . 117.2(4) ?
C11 C10 C9 . . 118.9(4) ?
C11 C10 H10 . . 120.5 ?
C9 C10 H10 . . 120.5 ?
C12 C11 C10 . . 122.5(4) ?
C12 C11 Br2 . . 118.5(4) ?
C10 C11 Br2 . . 119.0(3) ?
C11 C12 C13 . . 118.4(4) ?
C11 C12 H12 . . 120.8 ?
C13 C12 H12 . . 120.8 ?
C14 C13 C12 . . 120.4(4) ?
C14 C13 H13 . . 119.8 ?
C12 C13 H13 . . 119.8 ?
C13 C14 C9 . . 120.6(4) ?
C13 C14 H14 . . 119.7 ?
C9 C14 H14 . . 119.7 ?
O2 C15 N2 . . 122.2(4) ?
O2 C15 C16 . . 122.3(4) ?
N2 C15 C16 . . 115.5(4) ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C3 . 1.897(5) ?
O1 C7 . 1.209(5) ?
N1 C7 . 1.346(5) ?
N1 C1 . 1.398(5) ?
N1 H1N . 0.8600 ?
C1 C2 . 1.394(6) ?
C1 C6 . 1.400(6) ?
C2 C3 . 1.372(6) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.364(7) ?
C4 C5 . 1.390(7) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.377(7) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.514(6) ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
Br2 C11 . 1.895(4) ?
O2 C15 . 1.220(5) ?
N2 C15 . 1.349(5) ?
N2 C9 . 1.411(5) ?
N2 H2N . 0.8600 ?
C9 C10 . 1.383(5) ?
C9 C14 . 1.392(6) ?
C10 C11 . 1.374(6) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.369(6) ?
C12 C13 . 1.377(6) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.371(6) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 C16 . 1.490(6) ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 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 H1N O2 4_745 0.86 2.05 2.887(5) 166
N2 H2N O1 . 0.86 2.10 2.953(5) 169
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N1 C1 C2 . . . . -22.3(7) ?
C7 N1 C1 C6 . . . . 160.8(4) ?
N1 C1 C2 C3 . . . . -177.9(4) ?
C6 C1 C2 C3 . . . . -1.0(7) ?
C1 C2 C3 C4 . . . . 0.4(7) ?
C1 C2 C3 Br1 . . . . 177.6(3) ?
C2 C3 C4 C5 . . . . -0.4(8) ?
Br1 C3 C4 C5 . . . . -177.6(4) ?
C3 C4 C5 C6 . . . . 1.0(8) ?
C4 C5 C6 C1 . . . . -1.7(8) ?
C2 C1 C6 C5 . . . . 1.7(7) ?
N1 C1 C6 C5 . . . . 178.7(4) ?
C1 N1 C7 O1 . . . . -3.1(8) ?
C1 N1 C7 C8 . . . . 177.9(4) ?
C15 N2 C9 C10 . . . . 21.5(6) ?
C15 N2 C9 C14 . . . . -160.2(4) ?
C14 C9 C10 C11 . . . . 0.7(6) ?
N2 C9 C10 C11 . . . . 178.9(4) ?
C9 C10 C11 C12 . . . . -0.5(7) ?
C9 C10 C11 Br2 . . . . 178.0(3) ?
C10 C11 C12 C13 . . . . 0.7(7) ?
Br2 C11 C12 C13 . . . . -177.8(4) ?
C11 C12 C13 C14 . . . . -1.1(7) ?
C12 C13 C14 C9 . . . . 1.2(7) ?
C10 C9 C14 C13 . . . . -1.0(6) ?
N2 C9 C14 C13 . . . . -179.4(4) ?
C9 N2 C15 O2 . . . . 2.2(7) ?
C9 N2 C15 C16 . . . . -179.9(4) ?
