#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:10:11 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178460 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/81/4028176.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4028176
loop_
_publ_author_name
'Jérémie Mandel'
'Xiaohong Pan'
'E. Ben Hay'
'Steven J. Geib'
'Craig S. Wilcox'
'Dennis P. Curran'
_publ_section_title
;
 Rotational Isomers of N-Methyl-N-arylacetamides and Their Derived
 Enolates: Implications for Asymmetric Hartwig Oxindole Cyclizations
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4083
_journal_page_last               4089
_journal_paper_doi               10.1021/jo400385t
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C18 H20 Br N O'
_chemical_formula_weight         346.26
_chemical_name_systematic
; 
 ? 
;
_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                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.650(5)
_cell_length_b                   12.429(7)
_cell_length_c                   14.078(7)
_cell_measurement_temperature    203(2)
_cell_volume                     1688.5(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker Smart Apex CCD'
_diffrn_measurement_method       'omega scans'
_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  0.0563
_diffrn_reflns_av_sigmaI/netI    0.0873
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20984
_diffrn_reflns_theta_full        30.51
_diffrn_reflns_theta_max         32.51
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    2.433
_exptl_absorpt_correction_T_max  0.5703
_exptl_absorpt_correction_T_min  0.0112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker Sadabs'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       'rectangular prism'
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.606
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.005(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.944
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         5694
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.944
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0515
_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)+(0.0780P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1301
_refine_ls_wR_factor_ref         0.1637
_reflns_number_gt                3113
_reflns_number_total             5694
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400385t_si_002.cif
_cod_data_source_block           jmc691bs
_cod_original_cell_volume        1688.4(15)
_cod_database_code               4028176
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br Br 0.66459(5) 0.76155(4) 1.01795(3) 0.08003(19) Uani 1 1 d .
N N 0.6227(3) 0.6451(3) 0.8272(2) 0.0547(7) Uani 1 1 d .
O O 0.5458(3) 0.7786(3) 0.7344(3) 0.0907(10) Uani 1 1 d .
C1 C 0.7600(3) 0.6379(3) 0.9735(2) 0.0533(8) Uani 1 1 d .
C2 C 0.8620(4) 0.5922(3) 1.0301(3) 0.0570(8) Uani 1 1 d .
H2A H 0.8840 0.6232 1.0891 0.068 Uiso 1 1 calc R
C3 C 0.9308(3) 0.5017(3) 0.9997(3) 0.0556(9) Uani 1 1 d .
C4 C 0.8965(3) 0.4583(3) 0.9114(3) 0.0518(8) Uani 1 1 d .
H4A H 0.9429 0.3963 0.8903 0.062 Uiso 1 1 calc R
C5 C 0.7966(3) 0.5038(3) 0.8540(2) 0.0513(8) Uani 1 1 d .
C6 C 0.7287(3) 0.5968(3) 0.8844(2) 0.0507(7) Uani 1 1 d .
C7 C 1.0395(5) 0.4499(4) 1.0609(4) 0.0782(12) Uani 1 1 d .
H7A H 1.0494 0.4904 1.1194 0.117 Uiso 1 1 calc R
H7B H 1.1272 0.4492 1.0272 0.117 Uiso 1 1 calc R
H7C H 1.0121 0.3767 1.0755 0.117 Uiso 1 1 calc R
C8 C 0.7614(4) 0.4526(4) 0.7606(3) 0.0662(10) Uani 1 1 d .
H8A H 0.6898 0.4944 0.7293 0.099 Uiso 1 1 calc R
H8B H 0.7280 0.3800 0.7714 0.099 Uiso 1 1 calc R
H8C H 0.8434 0.4503 0.7209 0.099 Uiso 1 1 calc R
C9 C 0.4832(4) 0.6012(5) 0.8399(3) 0.0783(13) Uani 1 1 d .
H9A H 0.4190 0.6390 0.7987 0.117 Uiso 1 1 calc R
H9B H 0.4548 0.6101 0.9055 0.117 Uiso 1 1 calc R
H9C H 0.4833 0.5253 0.8238 0.117 Uiso 1 1 calc R
C10 C 0.6416(4) 0.7355(3) 0.7754(3) 0.0605(9) Uani 1 1 d .
C11 C 0.7895(4) 0.7797(3) 0.7679(3) 0.0581(8) Uani 1 1 d .
H11A H 0.8365 0.7703 0.8298 0.070 Uiso 1 1 calc R
C12 C 1.0078(4) 0.6896(3) 0.7121(3) 0.0668(10) Uani 1 1 d .
H12A H 1.0433 0.6983 0.7738 0.080 Uiso 1 1 calc R
C13 C 1.0898(6) 0.6457(4) 0.6434(5) 0.0890(16) Uani 1 1 d .
H13A H 1.1822 0.6276 0.6573 0.107 Uiso 1 1 calc R
C14 C 1.0396(5) 0.6286(5) 0.5568(5) 0.0969(18) Uani 1 1 d .
H14A H 1.0955 0.5947 0.5111 0.116 Uiso 1 1 calc R
C15 C 0.9079(6) 0.6595(5) 0.5329(4) 0.0944(16) Uani 1 1 d .
H15A H 0.8752 0.6499 0.4706 0.113 Uiso 1 1 calc R
C16 C 0.8222(4) 0.7057(4) 0.6023(3) 0.0691(10) Uani 1 1 d .
H16A H 0.7309 0.7256 0.5869 0.083 Uiso 1 1 calc R
C17 C 0.8717(3) 0.7218(3) 0.6925(2) 0.0503(7) Uani 1 1 d .
C18 C 0.7835(5) 0.9005(4) 0.7442(4) 0.0854(13) Uiso 1 1 d .
H18A H 0.8769 0.9289 0.7399 0.128 Uiso 1 1 calc R
H18B H 0.7333 0.9381 0.7938 0.128 Uiso 1 1 calc R
H18C H 0.7364 0.9106 0.6839 0.128 Uiso 1 1 calc R
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
C10 N C6 123.6(3)
C10 N C9 120.0(3)
C6 N C9 115.6(3)
C2 C1 C6 121.5(3)
C2 C1 Br 119.1(3)
C6 C1 Br 119.4(3)
C3 C2 C1 119.9(3)
C3 C2 H2A 120.0
C1 C2 H2A 120.0
C2 C3 C4 118.6(3)
C2 C3 C7 120.6(4)
C4 C3 C7 120.7(4)
C5 C4 C3 122.0(3)
C5 C4 H4A 119.0
C3 C4 H4A 119.0
C6 C5 C4 119.2(3)
C6 C5 C8 120.9(3)
C4 C5 C8 119.9(3)
C5 C6 C1 118.6(3)
C5 C6 N 120.7(3)
C1 C6 N 120.6(3)
C3 C7 H7A 109.5
C3 C7 H7B 109.5
H7A C7 H7B 109.5
C3 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C5 C8 H8A 109.5
C5 C8 H8B 109.5
H8A C8 H8B 109.5
C5 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
N C9 H9A 109.5
N C9 H9B 109.5
H9A C9 H9B 109.5
N C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
O C10 N 121.4(4)
O C10 C11 121.1(4)
N C10 C11 117.5(3)
C17 C11 C10 111.5(3)
C17 C11 C18 109.5(4)
C10 C11 C18 109.2(3)
C17 C11 H11A 108.9
C10 C11 H11A 108.9
C18 C11 H11A 108.8
C13 C12 C17 121.2(5)
C13 C12 H12A 119.4
C17 C12 H12A 119.4
C14 C13 C12 120.2(5)
C14 C13 H13A 119.9
C12 C13 H13A 119.9
C13 C14 C15 121.2(5)
C13 C14 H14A 119.4
C15 C14 H14A 119.4
C16 C15 C14 119.4(5)
C16 C15 H15A 120.3
C14 C15 H15A 120.3
C17 C16 C15 119.9(4)
C17 C16 H16A 120.0
C15 C16 H16A 120.0
C16 C17 C12 117.9(4)
C16 C17 C11 122.5(3)
C12 C17 C11 119.4(4)
C11 C18 H18A 109.5
C11 C18 H18B 109.5
H18A C18 H18B 109.5
C11 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br C1 1.897(4)
N C10 1.352(5)
N C6 1.434(5)
N C9 1.463(5)
O C10 1.215(5)
C1 C2 1.388(5)
C1 C6 1.388(5)
C2 C3 1.375(6)
C2 H2A 0.9400
C3 C4 1.395(5)
C3 C7 1.502(6)
C4 C5 1.379(5)
C4 H4A 0.9400
C5 C6 1.396(5)
C5 C8 1.500(5)
C7 H7A 0.9700
C7 H7B 0.9700
C7 H7C 0.9700
C8 H8A 0.9700
C8 H8B 0.9700
C8 H8C 0.9700
C9 H9A 0.9700
C9 H9B 0.9700
C9 H9C 0.9700
C10 C11 1.533(5)
C11 C17 1.508(5)
C11 C18 1.539(7)
C11 H11A 0.9900
C12 C13 1.363(7)
C12 C17 1.401(5)
C12 H12A 0.9400
C13 C14 1.329(9)
C13 H13A 0.9400
C14 C15 1.369(8)
C14 H14A 0.9400
C15 C16 1.402(7)
C15 H15A 0.9400
C16 C17 1.372(5)
C16 H16A 0.9400
C18 H18A 0.9700
C18 H18B 0.9700
C18 H18C 0.9700
