#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/97/2239702.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_2239702
loop_
_publ_author_name
'Abo-Amer, Anwar'
'Al-Refai, Mahmoud'
'Puddephatt, Richard J.'
'Ali, Basem F.'
_publ_section_title
;
 3-Bromo-N-(3,5-di-tert-butylphenyl)propanamide
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o770
_journal_paper_doi               10.1107/S1600536814012094
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C17 H26 Br N O'
_chemical_formula_moiety         'C17 H26 Br N O'
_chemical_formula_sum            'C17 H26 Br N O'
_chemical_formula_weight         340.30
_chemical_name_systematic
;
3-Bromo-N-(3,5-di-tert-butylphenyl)propanamide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 97.436(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.666(2)
_cell_length_b                   11.4885(16)
_cell_length_c                   9.7829(14)
_cell_measurement_reflns_used    5619
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.20
_cell_volume                     1745.9(4)
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_molecular_graphics    'CrystalMaker (CrystalMaker, 2014)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            21557
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.557
_diffrn_reflns_theta_min         2.205
_exptl_absorpt_coefficient_mu    2.351
_exptl_absorpt_correction_T_max  0.7887
_exptl_absorpt_correction_T_min  0.4546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2013)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.398
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.106
_refine_diff_density_max         1.075
_refine_diff_density_min         -0.645
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         4005
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0503
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0743P)²+1.5001P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1450
_reflns_number_gt                2738
_reflns_number_total             4005
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nk2223sup1.cif
_cod_data_source_block           I
_cod_database_code               2239702
_cod_database_fobs_code          2239702
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.455
_shelx_estimated_absorpt_t_max   0.789
_shelxl_version_number           .2013
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_occupancy
Br Br1 0.58935(3) 0.54272(3) 0.85526(5) 0.04516(17) Uani d 1
N N1 0.61402(17) 0.2102(2) 0.8672(2) 0.0205(6) Uani d 1
H H1C 0.5990 0.2131 0.9508 0.025 Uiso calc 1
O O1 0.57853(15) 0.2805(2) 0.6495(2) 0.0292(6) Uani d 1
C C1 0.4854(2) 0.4604(3) 0.7774(4) 0.0303(8) Uani d 1
H H1A 0.4344 0.4974 0.8092 0.036 Uiso calc 1
H H1B 0.4790 0.4653 0.6756 0.036 Uiso calc 1
C C2 0.4901(2) 0.3353(3) 0.8208(3) 0.0234(7) Uani d 1
H H2A 0.4358 0.2957 0.7840 0.028 Uiso calc 1
H H2B 0.4961 0.3308 0.9227 0.028 Uiso calc 1
C C3 0.56518(19) 0.2730(3) 0.7699(3) 0.0201(6) Uani d 1
C C4 0.68642(19) 0.1401(3) 0.8510(3) 0.0201(6) Uani d 1
C C5 0.74057(19) 0.1639(3) 0.7525(3) 0.0219(7) Uani d 1
H H5 0.7282 0.2270 0.6904 0.026 Uiso calc 1
C C6 0.81286(19) 0.0950(3) 0.7452(3) 0.0226(7) Uani d 1
C C7 0.8718(2) 0.1217(3) 0.6355(3) 0.0267(7) Uani d 1
C C8 0.8922(3) 0.2519(4) 0.6334(5) 0.0476(11) Uani d 1
H H8A 0.9299 0.2674 0.5631 0.071 Uiso calc 1
H H8B 0.9211 0.2757 0.7240 0.071 Uiso calc 1
H H8C 0.8386 0.2959 0.6118 0.071 Uiso calc 1
C C9 0.8285(2) 0.0018(3) 0.8365(3) 0.0240(7) Uani d 1
H H9 0.8774 -0.0460 0.8308 0.029 Uiso calc 1
C C10 0.7749(2) -0.0236(3) 0.9359(3) 0.0222(7) Uani d 1
C C11 0.7922(2) -0.1243(3) 1.0380(3) 0.0263(7) Uani d 1
C C12 0.7155(3) -0.2089(4) 1.0182(5) 0.0467(10) Uani d 1
H H12A 0.6632 -0.1682 1.0367 0.070 Uiso calc 1
H H12B 0.7267 -0.2745 1.0820 0.070 Uiso calc 1
H H12C 0.7077 -0.2378 0.9232 0.070 Uiso calc 1
C C13 0.8033(3) -0.0751(3) 1.1850(4) 0.0364(9) Uani d 1
H H13A 0.8532 -0.0231 1.1975 0.055 Uiso calc 1
H H13B 0.8122 -0.1393 1.2514 0.055 Uiso calc 1
H H13C 0.7515 -0.0316 1.2001 0.055 Uiso calc 1
C C14 0.8740(2) -0.1920(3) 1.0187(4) 0.0355(9) Uani d 1
H H14A 0.8691 -0.2226 0.9245 0.053 Uiso calc 1
H H14B 0.8813 -0.2567 1.0844 0.053 Uiso calc 1
H H14C 0.9238 -0.1400 1.0349 0.053 Uiso calc 1
C C15 0.7037(2) 0.0485(3) 0.9422(3) 0.0218(6) Uani d 1
H H15 0.6666 0.0344 1.0100 0.026 Uiso calc 1
C C16 0.8254(2) 0.0852(4) 0.4948(4) 0.0385(9) Uani d 1
H H16A 0.7720 0.1299 0.4744 0.058 Uiso calc 1
H H16B 0.8119 0.0020 0.4961 0.058 Uiso calc 1
H H16C 0.8626 0.1004 0.4236 0.058 Uiso calc 1
C C17 0.9571(2) 0.0552(4) 0.6613(4) 0.0412(10) Uani d 1
H H17A 0.9459 -0.0285 0.6509 0.062 Uiso calc 1
H H17B 0.9849 0.0712 0.7549 0.062 Uiso calc 1
H H17C 0.9949 0.0802 0.5945 0.062 Uiso calc 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
C3 N1 C4 127.9(2)
C3 N1 H1C 116.1
C4 N1 H1C 116.1
C2 C1 Br1 110.3(2)
C2 C1 H1A 109.6
Br1 C1 H1A 109.6
C2 C1 H1B 109.6
Br1 C1 H1B 109.6
H1A C1 H1B 108.1
C1 C2 C3 111.8(3)
C1 C2 H2A 109.2
C3 C2 H2A 109.2
C1 C2 H2B 109.2
C3 C2 H2B 109.2
H2A C2 H2B 107.9
O1 C3 N1 124.3(3)
O1 C3 C2 121.2(3)
N1 C3 C2 114.5(3)
C15 C4 C5 120.7(3)
C15 C4 N1 116.9(3)
C5 C4 N1 122.3(3)
C4 C5 C6 119.9(3)
C4 C5 H5 120.1
C6 C5 H5 120.1
C5 C6 C9 118.7(3)
C5 C6 C7 119.4(3)
C9 C6 C7 121.9(3)
C8 C7 C16 109.3(3)
C8 C7 C17 108.2(3)
C16 C7 C17 108.3(3)
C8 C7 C6 110.5(3)
C16 C7 C6 108.4(3)
C17 C7 C6 112.1(3)
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
C6 C9 C10 122.3(3)
C6 C9 H9 118.9
C10 C9 H9 118.9
C9 C10 C15 117.6(3)
C9 C10 C11 122.7(3)
C15 C10 C11 119.7(3)
C10 C11 C14 112.6(3)
C10 C11 C13 108.8(3)
C14 C11 C13 107.9(3)
C10 C11 C12 109.0(3)
C14 C11 C12 108.4(3)
C13 C11 C12 110.0(3)
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C11 C13 H13A 109.5
C11 C13 H13B 109.5
H13A C13 H13B 109.5
C11 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C11 C14 H14A 109.5
C11 C14 H14B 109.5
H14A C14 H14B 109.5
C11 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C4 C15 C10 120.9(3)
C4 C15 H15 119.6
C10 C15 H15 119.6
C7 C16 H16A 109.5
C7 C16 H16B 109.5
H16A C16 H16B 109.5
C7 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C7 C17 H17A 109.5
C7 C17 H17B 109.5
H17A C17 H17B 109.5
C7 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.951(4)
N1 C3 1.350(4)
N1 C4 1.416(4)
N1 H1C 0.8800
O1 C3 1.226(4)
C1 C2 1.498(5)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C3 1.515(4)
C2 H2A 0.9900
C2 H2B 0.9900
C4 C15 1.384(4)
C4 C5 1.391(4)
C5 C6 1.391(4)
C5 H5 0.9500
C6 C9 1.396(5)
C6 C7 1.534(4)
C7 C8 1.530(6)
C7 C16 1.530(5)
C7 C17 1.531(5)
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 C10 1.396(5)
C9 H9 0.9500
C10 C15 1.397(4)
C10 C11 1.529(5)
C11 C14 1.531(5)
C11 C13 1.534(5)
C11 C12 1.538(5)
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 H15 0.9500
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 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
_geom_hbond_publ_flag
N1 H1C O1 4_566 0.88 2.01 2.889(3) 174.0 y
C5 H5 O1 . 0.95 2.41 2.931(4) 114.6 .
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
Br1 C1 C2 C3 -61.5(3)
C4 N1 C3 O1 -1.8(5)
C4 N1 C3 C2 178.0(3)
C1 C2 C3 O1 -48.6(4)
C1 C2 C3 N1 131.6(3)
C3 N1 C4 C15 -153.2(3)
C3 N1 C4 C5 29.4(5)
C15 C4 C5 C6 0.0(5)
N1 C4 C5 C6 177.3(3)
C4 C5 C6 C9 1.0(5)
C4 C5 C6 C7 179.7(3)
C5 C6 C7 C8 47.2(4)
C9 C6 C7 C8 -134.1(3)
C5 C6 C7 C16 -72.6(4)
C9 C6 C7 C16 106.1(4)
C5 C6 C7 C17 167.9(3)
C9 C6 C7 C17 -13.4(4)
C5 C6 C9 C10 -0.9(5)
C7 C6 C9 C10 -179.6(3)
C6 C9 C10 C15 -0.2(5)
C6 C9 C10 C11 -179.0(3)
C9 C10 C11 C14 0.3(4)
C15 C10 C11 C14 -178.5(3)
C9 C10 C11 C13 119.9(3)
C15 C10 C11 C13 -58.9(4)
C9 C10 C11 C12 -120.1(4)
C15 C10 C11 C12 61.1(4)
C5 C4 C15 C10 -1.2(5)
N1 C4 C15 C10 -178.6(3)
C9 C10 C15 C4 1.3(5)
C11 C10 C15 C4 -179.9(3)
