#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/94/2209469.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_2209469
loop_
_publ_author_name
'Jian-Ying Huang'
'Wei Xu'
_publ_section_title
;
 N-(2-Bromophenyl)-2-phenylpropanamide
;
_journal_coeditor_code           DN2035
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2651
_journal_page_last               o2652
_journal_paper_doi               10.1107/S1600536806019714
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C15 H14 Br N O'
_chemical_formula_moiety         'C15 H14 Br N O'
_chemical_formula_sum            'C15 H14 Br N O'
_chemical_formula_weight         304.18
_chemical_name_systematic
;
N-(2-Bromophenyl)-2-phenylpropanamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 95.97(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.587(2)
_cell_length_b                   13.756(3)
_cell_length_c                   8.433(2)
_cell_measurement_reflns_used    12871
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.45
_cell_measurement_theta_min      3.21
_cell_volume                     1336.9(5)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia,
1997)
and PLATON (Spek, 2003)
;
_computing_publication_material  'CrystalStructure and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_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  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11223
_diffrn_reflns_theta_full        26.04
_diffrn_reflns_theta_max         26.04
_diffrn_reflns_theta_min         3.21
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.062
_exptl_absorpt_correction_T_max  0.546
_exptl_absorpt_correction_T_min  0.288
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.505
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2590
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0368
_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)+(0.0474P)²+0.2146P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0969
_reflns_number_gt                1687
_reflns_number_total             2590
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2035.cif
_cod_data_source_block           I
_cod_original_cell_volume        1336.8(5)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               2209469
_cod_database_fobs_code          2209469
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
Br Br 0.34778(3) 0.00196(2) 0.10974(4) 0.08081(18) Uani d . 1
N N 0.32306(17) 0.22386(15) 0.1190(2) 0.0464(5) Uani d . 1
H H0 0.3094 0.1955 0.0281 0.056 Uiso calc R 1
O O 0.26233(15) 0.34368(13) 0.2751(2) 0.0542(5) Uani d . 1
C C1 0.0309(3) 0.1654(2) 0.0568(4) 0.0662(8) Uani d . 1
H H1 0.0875 0.1310 0.0099 0.079 Uiso calc R 1
C C2 -0.0638(3) 0.1158(3) 0.1042(4) 0.0819(10) Uani d . 1
H H2 -0.0701 0.0489 0.0891 0.098 Uiso calc R 1
C C3 -0.1474(3) 0.1650(4) 0.1728(4) 0.0832(11) Uani d . 1
H H3 -0.2117 0.1322 0.2035 0.100 Uiso calc R 1
C C4 -0.1366(3) 0.2616(3) 0.1959(4) 0.0827(11) Uani d . 1
H H4 -0.1934 0.2950 0.2440 0.099 Uiso calc R 1
C C5 -0.0420(3) 0.3122(2) 0.1491(4) 0.0678(8) Uani d . 1
H H5 -0.0362 0.3788 0.1663 0.081 Uiso calc R 1
C C6 0.0435(2) 0.2642(2) 0.0773(3) 0.0486(6) Uani d . 1
C C7 0.1494(2) 0.31407(19) 0.0251(3) 0.0474(6) Uani d . 1
H H7 0.1679 0.2827 -0.0735 0.057 Uiso calc R 1
C C8 0.1364(3) 0.4225(2) -0.0079(4) 0.0701(9) Uani d . 1
H H8A 0.0683 0.4338 -0.0805 0.105 Uiso calc R 1
H H8B 0.2035 0.4458 -0.0541 0.105 Uiso calc R 1
H H8C 0.1294 0.4563 0.0902 0.105 Uiso calc R 1
C C9 0.2510(2) 0.29679(18) 0.1515(3) 0.0423(6) Uani d . 1
C C10 0.4910(2) 0.2538(2) 0.3119(3) 0.0540(7) Uani d . 1
H H10 0.4762 0.3202 0.3061 0.065 Uiso calc R 1
C C11 0.5845(2) 0.2201(2) 0.4102(3) 0.0608(8) Uani d . 1
H H11 0.6314 0.2635 0.4719 0.073 Uiso calc R 1
C C12 0.6084(3) 0.1230(3) 0.4172(4) 0.0705(8) Uani d . 1
H H12 0.6713 0.1003 0.4847 0.085 Uiso calc R 1
C C13 0.5404(3) 0.0589(2) 0.3257(4) 0.0712(9) Uani d . 1
H H13 0.5585 -0.0070 0.3277 0.085 Uiso calc R 1
C C14 0.4447(2) 0.0925(2) 0.2300(3) 0.0517(7) Uani d . 1
C C15 0.4186(2) 0.19026(18) 0.2212(3) 0.0442(6) Uani d . 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'
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'
Br Br -0.2901 2.4595 '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
C9 N C15 125.6(2)
C9 N H0 117.2
C15 N H0 117.2
C6 C1 C2 121.8(3)
C6 C1 H1 119.1
C2 C1 H1 119.1
C3 C2 C1 119.9(4)
C3 C2 H2 120.1
C1 C2 H2 120.1
C4 C3 C2 119.5(3)
C4 C3 H3 120.2
C2 C3 H3 120.2
C3 C4 C5 121.2(3)
C3 C4 H4 119.4
C5 C4 H4 119.4
C6 C5 C4 120.5(3)
C6 C5 H5 119.7
C4 C5 H5 119.7
C1 C6 C5 117.1(3)
C1 C6 C7 119.4(2)
C5 C6 C7 123.5(3)
C6 C7 C8 115.5(2)
C6 C7 C9 108.5(2)
C8 C7 C9 109.6(2)
C6 C7 H7 107.7
C8 C7 H7 107.7
C9 C7 H7 107.7
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
O C9 N 123.5(2)
O C9 C7 121.5(2)
N C9 C7 115.0(2)
C11 C10 C15 121.0(3)
C11 C10 H10 119.5
C15 C10 H10 119.5
C12 C11 C10 120.0(3)
C12 C11 H11 120.0
C10 C11 H11 120.0
C11 C12 C13 120.3(3)
C11 C12 H12 119.9
C13 C12 H12 119.9
C12 C13 C14 119.7(3)
C12 C13 H13 120.2
C14 C13 H13 120.2
C15 C14 C13 121.1(3)
C15 C14 Br 119.8(2)
C13 C14 Br 119.1(2)
C14 C15 C10 117.9(2)
C14 C15 N 120.5(2)
C10 C15 N 121.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br C14 1.898(3)
N C9 1.351(3)
N C15 1.408(3)
N H0 0.8600
O C9 1.221(3)
C1 C6 1.376(4)
C1 C2 1.386(4)
C1 H1 0.9300
C2 C3 1.359(5)
C2 H2 0.9300
C3 C4 1.347(5)
C3 H3 0.9300
C4 C5 1.389(4)
C4 H4 0.9300
C5 C6 1.382(4)
C5 H5 0.9300
C6 C7 1.510(4)
C7 C8 1.522(4)
C7 C9 1.523(3)
C7 H7 0.9800
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C10 C11 1.374(4)
C10 C15 1.386(4)
C10 H10 0.9300
C11 C12 1.365(4)
C11 H11 0.9300
C12 C13 1.367(4)
C12 H12 0.9300
C13 C14 1.381(4)
C13 H13 0.9300
C14 C15 1.379(4)
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
N H0 O 4_565 0.86 2.21 3.057(3) 167
