#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/04/2230423.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_2230423
loop_
_publ_author_name
'Moreno-Fuquen, Rodolfo'
'Quintero, David E.'
'Zuluaga, Fabio'
'Kennedy, Alan R.'
'De Almeida Santos, Regina H.'
_publ_section_title
;
 2-Bromo-2-methyl-N-p-tolylpropanamide
;
_journal_coeditor_code           LH5254
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1543
_journal_paper_doi               10.1107/S1600536811019337
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C11 H14 Br N O'
_chemical_formula_moiety         'C11 H14 Br N O'
_chemical_formula_sum            'C11 H14 Br N O'
_chemical_formula_weight         256.14
_chemical_melting_point          385.0(10)
_chemical_name_systematic
;
2-Bromo-2-methyl-N-p-tolylpropanamide
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   10.0728(4)
_cell_length_b                   11.2577(4)
_cell_length_c                   20.3670(6)
_cell_measurement_reflns_used    2266
_cell_measurement_temperature    123
_cell_measurement_theta_max      29.45
_cell_measurement_theta_min      3.36
_cell_volume                     2309.55(14)
_computing_cell_refinement       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur E'
_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  0.0486
_diffrn_reflns_av_sigmaI/netI    0.0538
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10140
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         3.37
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.529
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.576
_refine_diff_density_min         -0.456
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         2762
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0453
_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)+(0.0316P)²+0.7321P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0930
_reflns_number_gt                1819
_reflns_number_total             2762
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5254.cif
_cod_data_source_block           I
_cod_database_code               2230423
_cod_database_fobs_code          2230423
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'
'-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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.74332(3) 0.28652(3) 0.384590(15) 0.02982(13) Uani d . 1 1 . .
O O1 0.94616(17) 0.2851(2) 0.24129(10) 0.0200(5) Uani d . 1 1 . .
N N1 0.7262(2) 0.2730(3) 0.21911(12) 0.0158(6) Uani d D 1 1 . .
C C1 0.6864(3) 0.4811(3) 0.30022(16) 0.0214(7) Uani d . 1 1 . .
H H1A 0.7056 0.5288 0.2611 0.032 Uiso calc R 1 1 . .
H H1B 0.6768 0.5335 0.3384 0.032 Uiso calc R 1 1 . .
H H1C 0.6037 0.4368 0.2935 0.032 Uiso calc R 1 1 . .
C C2 0.7996(3) 0.3946(3) 0.31211(15) 0.0173(7) Uani d . 1 1 . .
C C3 0.9232(3) 0.4587(3) 0.33541(16) 0.0287(9) Uani d . 1 1 . .
H H3A 0.9914 0.4004 0.3472 0.043 Uiso calc R 1 1 . .
H H3B 0.9015 0.5073 0.3739 0.043 Uiso calc R 1 1 . .
H H3C 0.9565 0.5100 0.3002 0.043 Uiso calc R 1 1 . .
C C4 0.8312(3) 0.3116(3) 0.25448(14) 0.0158(7) Uani d . 1 1 . .
C C5 0.7307(2) 0.1928(3) 0.16557(14) 0.0160(7) Uani d . 1 1 . .
C C6 0.8384(3) 0.1847(3) 0.12261(14) 0.0203(7) Uani d . 1 1 . .
H H6 0.9135 0.2348 0.1281 0.024 Uiso calc R 1 1 . .
C C7 0.8347(3) 0.1030(3) 0.07213(15) 0.0241(8) Uani d . 1 1 . .
H H7 0.9082 0.0986 0.0431 0.029 Uiso calc R 1 1 . .
C C8 0.7285(3) 0.0274(3) 0.06198(15) 0.0229(8) Uani d . 1 1 . .
C C9 0.6210(3) 0.0383(3) 0.10438(16) 0.0273(8) Uani d . 1 1 . .
H H9 0.5457 -0.0113 0.0985 0.033 Uiso calc R 1 1 . .
C C10 0.6216(3) 0.1202(3) 0.15499(15) 0.0225(8) Uani d . 1 1 . .
H H10 0.5463 0.1267 0.1829 0.027 Uiso calc R 1 1 . .
C C11 0.7287(3) -0.0636(4) 0.00758(17) 0.0338(9) Uani d . 1 1 . .
H H11A 0.6452 -0.1082 0.0085 0.051 Uiso calc PR 0.50 1 . .
H H11B 0.8033 -0.1184 0.0138 0.051 Uiso calc PR 0.50 1 . .
H H11C 0.7378 -0.0233 -0.0348 0.051 Uiso calc PR 0.50 1 . .
H H11D 0.8123 -0.0584 -0.0168 0.051 Uiso d PR 0.50 1 . .
H H11E 0.6542 -0.0482 -0.0222 0.051 Uiso d PR 0.50 1 . .
H H11F 0.7197 -0.1433 0.0264 0.051 Uiso d PR 0.50 1 . .
H H1N 0.652(2) 0.292(3) 0.2342(15) 0.032(10) Uiso d D 1 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Br Br -0.2901 2.4595 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
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
C4 N1 C5 . . 126.2(2) ?
C4 N1 H1N . . 115(2) ?
C5 N1 H1N . . 118(2) ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C3 C2 C1 . . 111.2(3) ?
C3 C2 C4 . . 111.1(2) ?
C1 C2 C4 . . 115.1(2) ?
C3 C2 Br1 . . 107.0(2) ?
C1 C2 Br1 . . 107.20(19) ?
C4 C2 Br1 . . 104.7(2) ?
C2 C3 H3A . . 109.5 ?
C2 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
C2 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
O1 C4 N1 . . 123.0(3) ?
O1 C4 C2 . . 120.8(3) ?
N1 C4 C2 . . 116.2(2) ?
C10 C5 C6 . . 118.7(3) ?
C10 C5 N1 . . 118.1(3) ?
C6 C5 N1 . . 123.3(3) ?
C7 C6 C5 . . 119.3(3) ?
C7 C6 H6 . . 120.4 ?
C5 C6 H6 . . 120.4 ?
C6 C7 C8 . . 122.9(3) ?
C6 C7 H7 . . 118.5 ?
C8 C7 H7 . . 118.5 ?
C7 C8 C9 . . 117.1(3) ?
C7 C8 C11 . . 121.8(3) ?
C9 C8 C11 . . 121.1(3) ?
C10 C9 C8 . . 121.2(3) ?
C10 C9 H9 . . 119.4 ?
C8 C9 H9 . . 119.4 ?
C9 C10 C5 . . 120.8(3) ?
C9 C10 H10 . . 119.6 ?
C5 C10 H10 . . 119.6 ?
C8 C11 H11A . . 109.5 ?
C8 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C8 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C8 C11 H11D . . 109.5 ?
H11A C11 H11D . . 141.1 ?
H11B C11 H11D . . 56.3 ?
H11C C11 H11D . . 56.3 ?
C8 C11 H11E . . 109.5 ?
H11A C11 H11E . . 56.3 ?
H11B C11 H11E . . 141.1 ?
H11C C11 H11E . . 56.3 ?
H11D C11 H11E . . 109.5 ?
C8 C11 H11F . . 109.5 ?
H11A C11 H11F . . 56.3 ?
H11B C11 H11F . . 56.3 ?
H11C C11 H11F . . 141.1 ?
H11D C11 H11F . . 109.5 ?
H11E C11 H11F . . 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 C2 . 1.995(3) ?
O1 C4 . 1.226(3) ?
N1 C4 . 1.352(4) ?
N1 C5 . 1.416(4) ?
N1 H1N . 0.840(17) ?
C1 C2 . 1.519(4) ?
C1 H1A . 0.9800 ?
C1 H1B . 0.9800 ?
C1 H1C . 0.9800 ?
C2 C3 . 1.515(4) ?
C2 C4 . 1.533(4) ?
C3 H3A . 0.9800 ?
C3 H3B . 0.9800 ?
C3 H3C . 0.9800 ?
C5 C10 . 1.387(4) ?
C5 C6 . 1.397(4) ?
C6 C7 . 1.380(4) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.382(4) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.391(4) ?
C8 C11 . 1.509(5) ?
C9 C10 . 1.382(4) ?
C9 H9 . 0.9500 ?
C10 H10 . 0.9500 ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
C11 H11D . 0.9800 ?
C11 H11E . 0.9800 ?
C11 H11F . 0.9800 ?
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 6_556 0.840(17) 2.13(2) 2.937(3) 161(3)
C1 H1C O1 6_556 0.98 2.44 3.382(4) 162
C10 H10 O1 6_556 0.95 2.57 3.321(4) 137
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
C5 N1 C4 O1 . . . . 4.0(5) ?
C5 N1 C4 C2 . . . . -177.5(3) ?
C3 C2 C4 O1 . . . . 14.6(4) ?
C1 C2 C4 O1 . . . . 142.0(3) ?
Br1 C2 C4 O1 . . . . -100.5(3) ?
C3 C2 C4 N1 . . . . -163.9(3) ?
C1 C2 C4 N1 . . . . -36.5(4) ?
Br1 C2 C4 N1 . . . . 81.0(3) ?
C4 N1 C5 C10 . . . . 149.7(3) ?
C4 N1 C5 C6 . . . . -31.2(5) ?
C10 C5 C6 C7 . . . . -1.6(5) ?
N1 C5 C6 C7 . . . . 179.3(3) ?
C5 C6 C7 C8 . . . . -0.4(5) ?
C6 C7 C8 C9 . . . . 1.6(5) ?
C6 C7 C8 C11 . . . . -178.2(3) ?
C7 C8 C9 C10 . . . . -1.0(5) ?
C11 C8 C9 C10 . . . . 178.8(3) ?
C8 C9 C10 C5 . . . . -0.9(5) ?
C6 C5 C10 C9 . . . . 2.2(5) ?
N1 C5 C10 C9 . . . . -178.6(3) ?
