#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/61/2226176.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_2226176
loop_
_publ_author_name
'Li, Huo Ming'
'Wu, Jin-Long'
_publ_section_title
;
 N-Benzyl-2-(2-bromophenyl)-2-(2-nitrophenoxy)acetamide
;
_journal_coeditor_code           IM2196
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1274
_journal_paper_doi               10.1107/S1600536810014996
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C21 H17 Br N2 O4'
_chemical_formula_moiety         'C21 H17 Br N2 O4'
_chemical_formula_sum            'C21 H17 Br N2 O4'
_chemical_formula_weight         441.28
_chemical_name_systematic
;
N-Benzyl-2-(2-bromophenyl)-2-(2-nitrophenoxy)acetamide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                73.939(6)
_cell_angle_beta                 82.878(6)
_cell_angle_gamma                74.447(6)
_cell_formula_units_Z            2
_cell_length_a                   7.5818(5)
_cell_length_b                   10.4650(7)
_cell_length_c                   13.1095(10)
_cell_measurement_reflns_used    3052
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.8920
_cell_measurement_theta_min      3.5106
_cell_volume                     961.56(12)
_computing_cell_refinement
;
CrysAlis Pro (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis Pro (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis Pro (Oxford Diffraction, 2009)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type
'Oxford Diffraction Xcalibur Atlas Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7135
_diffrn_reflns_theta_full        66.58
_diffrn_reflns_theta_max         66.58
_diffrn_reflns_theta_min         3.51
_exptl_absorpt_coefficient_mu    3.174
_exptl_absorpt_correction_T_max  0.565
_exptl_absorpt_correction_T_min  0.427
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis Pro; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.392
_refine_ls_extinction_coef       0.0258(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3363
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0378
_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)+(0.0523P)²+0.3500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1046
_reflns_number_gt                2522
_reflns_number_total             3363
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            im2196.cif
_cod_data_source_block           I
_cod_database_code               2226176
_cod_database_fobs_code          2226176
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_disorder_assembly
_atom_site_disorder_group
Br Br27 0.67572(5) 0.56595(4) 0.87665(3) 0.0848(2) Uani d . 1 . .
O O2 0.3651(3) 0.99683(19) 0.82814(14) 0.0599(5) Uani d . 1 . .
O O24 0.6787(3) 0.8846(3) 0.63093(18) 0.0856(7) Uani d . 1 . .
O O25 0.2519(5) 1.2538(2) 0.8109(2) 0.1010(9) Uani d . 1 . .
O O26 0.0566(5) 1.3176(3) 0.9264(3) 0.1318(13) Uani d . 1 . .
N N22 0.5004(4) 1.0913(3) 0.64616(19) 0.0712(7) Uani d . 1 . .
H H22 0.4153 1.1318 0.6846 0.085 Uiso calc R 1 . .
N N23 0.1698(4) 1.2288(3) 0.8964(2) 0.0653(7) Uani d . 1 . .
C C1 0.6438(6) 1.3641(4) 0.5979(3) 0.0878(11) Uani d . 1 . .
H H1 0.5190 1.4028 0.6064 0.105 Uiso calc R 1 . .
C C2 0.7724(10) 1.4280(5) 0.6178(3) 0.1174(18) Uani d . 1 . .
H H2 0.7341 1.5090 0.6395 0.141 Uiso calc R 1 . .
C C3 0.9541(11) 1.3690(8) 0.6046(4) 0.126(2) Uani d . 1 . .
H H3 1.0401 1.4101 0.6182 0.152 Uiso calc R 1 . .
C C4 1.0118(7) 1.2529(7) 0.5724(4) 0.1164(18) Uani d . 1 . .
H H4 1.1365 1.2150 0.5628 0.140 Uiso calc R 1 . .
C C5 0.8863(5) 1.1907(4) 0.5537(3) 0.0829(10) Uani d . 1 . .
H H5 0.9267 1.1098 0.5320 0.099 Uiso calc R 1 . .
C C6 0.7016(4) 1.2457(4) 0.5664(2) 0.0629(8) Uani d . 1 . .
C C7 0.5676(6) 1.1746(5) 0.5464(3) 0.0911(13) Uani d . 1 . .
H H7B 0.4646 1.2424 0.5108 0.109 Uiso calc R 1 . .
H H7A 0.6259 1.1159 0.4998 0.109 Uiso calc R 1 . .
C C8 0.5655(4) 0.9562(4) 0.6794(2) 0.0615(8) Uani d . 1 . .
C C9 0.4855(4) 0.8876(3) 0.7880(2) 0.0515(6) Uani d . 1 . .
H H9 0.5849 0.8396 0.8363 0.062 Uiso calc R 1 . .
C C10 0.3835(4) 0.7874(3) 0.7772(2) 0.0477(6) Uani d . 1 . .
C C11 0.4463(4) 0.6461(3) 0.8127(2) 0.0577(7) Uani d . 1 . .
C C12 0.3448(5) 0.5585(3) 0.8030(3) 0.0745(9) Uani d . 1 . .
H H12 0.3896 0.4642 0.8271 0.089 Uiso calc R 1 . .
C C13 0.1799(5) 0.6103(4) 0.7584(3) 0.0750(9) Uani d . 1 . .
H H13 0.1110 0.5511 0.7532 0.090 Uiso calc R 1 . .
C C14 0.1141(4) 0.7491(4) 0.7209(2) 0.0673(8) Uani d . 1 . .
H H14 0.0017 0.7842 0.6895 0.081 Uiso calc R 1 . .
C C15 0.2163(4) 0.8368(3) 0.7301(2) 0.0558(7) Uani d . 1 . .
H H15 0.1716 0.9309 0.7040 0.067 Uiso calc R 1 . .
C C16 0.3115(4) 0.9775(3) 0.93255(19) 0.0460(6) Uani d . 1 . .
C C17 0.3463(4) 0.8503(3) 1.0060(2) 0.0544(7) Uani d . 1 . .
H H17 0.4134 0.7728 0.9846 0.065 Uiso calc R 1 . .
C C18 0.2821(4) 0.8388(3) 1.1098(2) 0.0631(8) Uani d . 1 . .
H H18 0.3077 0.7534 1.1583 0.076 Uiso calc R 1 . .
C C19 0.1805(4) 0.9514(4) 1.1434(2) 0.0698(9) Uani d . 1 . .
H H19 0.1373 0.9420 1.2140 0.084 Uiso calc R 1 . .
C C20 0.1435(4) 1.0772(3) 1.0723(2) 0.0628(8) Uani d . 1 . .
H H20 0.0739 1.1537 1.0943 0.075 Uiso calc R 1 . .
C C21 0.2096(4) 1.0908(3) 0.9674(2) 0.0488(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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C16 O2 C9 . . 121.1(2) ?
C8 N22 C7 . . 122.8(3) ?
C8 N22 H22 . . 118.6 ?
C7 N22 H22 . . 118.6 ?
O26 N23 O25 . . 120.9(3) ?
O26 N23 C21 . . 118.1(3) ?
O25 N23 C21 . . 120.9(3) ?
C6 C1 C2 . . 120.0(4) ?
C6 C1 H1 . . 120.0 ?
C2 C1 H1 . . 120.0 ?
C3 C2 C1 . . 118.7(5) ?
C3 C2 H2 . . 120.7 ?
C1 C2 H2 . . 120.7 ?
C4 C3 C2 . . 121.5(5) ?
C4 C3 H3 . . 119.3 ?
C2 C3 H3 . . 119.3 ?
C3 C4 C5 . . 119.6(5) ?
C3 C4 H4 . . 120.2 ?
C5 C4 H4 . . 120.2 ?
C4 C5 C6 . . 121.1(5) ?
C4 C5 H5 . . 119.4 ?
C6 C5 H5 . . 119.4 ?
C1 C6 C5 . . 119.1(4) ?
C1 C6 C7 . . 121.0(4) ?
C5 C6 C7 . . 119.9(4) ?
N22 C7 C6 . . 111.5(3) ?
N22 C7 H7B . . 109.3 ?
C6 C7 H7B . . 109.3 ?
N22 C7 H7A . . 109.3 ?
C6 C7 H7A . . 109.3 ?
H7B C7 H7A . . 108.0 ?
O24 C8 N22 . . 125.8(3) ?
O24 C8 C9 . . 118.7(3) ?
N22 C8 C9 . . 115.5(3) ?
O2 C9 C10 . . 111.1(2) ?
O2 C9 C8 . . 106.1(2) ?
C10 C9 C8 . . 111.0(2) ?
O2 C9 H9 . . 109.5 ?
C10 C9 H9 . . 109.5 ?
C8 C9 H9 . . 109.5 ?
C15 C10 C11 . . 117.2(3) ?
C15 C10 C9 . . 119.1(3) ?
C11 C10 C9 . . 123.7(2) ?
C12 C11 C10 . . 121.3(3) ?
C12 C11 Br27 . . 117.6(2) ?
C10 C11 Br27 . . 121.0(2) ?
C13 C12 C11 . . 120.1(3) ?
C13 C12 H12 . . 120.0 ?
C11 C12 H12 . . 120.0 ?
C12 C13 C14 . . 120.4(3) ?
C12 C13 H13 . . 119.8 ?
C14 C13 H13 . . 119.8 ?
C13 C14 C15 . . 119.5(3) ?
C13 C14 H14 . . 120.2 ?
C15 C14 H14 . . 120.2 ?
C10 C15 C14 . . 121.5(3) ?
C10 C15 H15 . . 119.3 ?
C14 C15 H15 . . 119.3 ?
O2 C16 C17 . . 123.9(2) ?
O2 C16 C21 . . 117.9(2) ?
C17 C16 C21 . . 118.2(2) ?
C18 C17 C16 . . 120.2(3) ?
C18 C17 H17 . . 119.9 ?
C16 C17 H17 . . 119.9 ?
C17 C18 C19 . . 121.2(3) ?
C17 C18 H18 . . 119.4 ?
C19 C18 H18 . . 119.4 ?
C20 C19 C18 . . 119.5(3) ?
C20 C19 H19 . . 120.2 ?
C18 C19 H19 . . 120.2 ?
C19 C20 C21 . . 120.0(3) ?
C19 C20 H20 . . 120.0 ?
C21 C20 H20 . . 120.0 ?
C20 C21 C16 . . 120.9(3) ?
C20 C21 N23 . . 117.2(3) ?
C16 C21 N23 . . 121.9(2) ?
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
Br27 C11 . 1.903(3) ?
O2 C16 . 1.354(3) ?
O2 C9 . 1.439(3) ?
O24 C8 . 1.218(4) ?
O25 N23 . 1.209(4) ?
O26 N23 . 1.203(4) ?
N22 C8 . 1.331(4) ?
N22 C7 . 1.473(4) ?
N22 H22 . 0.8600 ?
N23 C21 . 1.461(4) ?
C1 C6 . 1.358(5) ?
C1 C2 . 1.406(7) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.361(8) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.341(8) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.367(6) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.372(5) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.494(5) ?
C7 H7B . 0.9700 ?
C7 H7A . 0.9700 ?
C8 C9 . 1.538(4) ?
C9 C10 . 1.504(4) ?
C9 H9 . 0.9800 ?
C10 C15 . 1.386(4) ?
C10 C11 . 1.388(4) ?
C11 C12 . 1.384(4) ?
C12 C13 . 1.357(5) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.370(5) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.387(4) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
C16 C17 . 1.391(4) ?
C16 C21 . 1.391(4) ?
C17 C18 . 1.371(4) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.375(5) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.367(5) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.386(4) ?
C20 H20 . 0.9300 ?
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
N22 H22 O2 1_555 0.86 2.08 2.521(3) 111
N22 H22 O25 1_555 0.86 2.39 3.227(4) 164
