#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:59:08 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178968 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/97/4119739.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_4119739
loop_
_publ_author_name
'Hongyin Gao'
'Daniel H. Ess'
'Muhammed Yousufuddin'
'László Kürti'
_publ_section_title
;
 Transition-Metal-Free Direct Arylation: Synthesis of Halogenated
 2-Amino-2'-hydroxy-1,1'-biaryls and Mechanism by DFT Calculations
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7086
_journal_page_last               7089
_journal_paper_doi               10.1021/ja400897u
_journal_volume                  135
_journal_year                    2013
_chemical_formula_sum            'C12 H10 Br N O'
_chemical_formula_weight         264.12
_chemical_name_systematic
; 
 ? 
;
_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                 100.364(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.6597(12)
_cell_length_b                   13.388(3)
_cell_length_c                   16.692(4)
_cell_measurement_reflns_used    4421
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.17
_cell_measurement_theta_min      2.48
_cell_volume                     1024.3(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω 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  0.0553
_diffrn_reflns_av_sigmaI/netI    0.0486
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9601
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    3.982
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_description       needle
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.428
_refine_diff_density_min         -1.353
_refine_diff_density_rms         0.139
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2538
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0397
_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)+(0.0625P)²+0.4748P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1083
_reflns_number_gt                2185
_reflns_number_total             2538
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja400897u_si_002.cif
_cod_data_source_block           laszlo7m
_cod_database_code               4119739
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_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
Br1 Br 0.18811(5) 0.839719(18) 0.391644(15) 0.02135(13) Uani 1 1 d .
O1 O -0.1372(4) 0.52314(13) 0.56873(12) 0.0187(4) Uani 1 1 d .
H1O H -0.1787 0.4676 0.5494 0.028 Uiso 1 1 d R
N1 N 0.3823(5) 0.65504(14) 0.50060(14) 0.0164(4) Uani 1 1 d .
H1N H 0.5030 0.6258 0.5333 0.020 Uiso 1 1 d R
H2N H 0.4604 0.6825 0.4642 0.020 Uiso 1 1 d R
C1 C 0.0927(5) 0.80798(19) 0.49525(15) 0.0171(5) Uani 1 1 d .
C2 C -0.0852(5) 0.8738(2) 0.52834(17) 0.0198(5) Uani 1 1 d .
H2 H -0.1651 0.9292 0.4988 0.024 Uiso 1 1 calc R
C3 C -0.1422(6) 0.8560(2) 0.60597(17) 0.0213(6) Uani 1 1 d .
H3 H -0.2556 0.9004 0.6297 0.026 Uiso 1 1 calc R
C4 C -0.0269(5) 0.77060(19) 0.64785(17) 0.0198(5) Uani 1 1 d .
H4 H -0.0623 0.7592 0.7002 0.024 Uiso 1 1 calc R
C5 C 0.1399(5) 0.70195(18) 0.61330(15) 0.0166(5) Uani 1 1 d .
C6 C 0.2087(5) 0.72203(18) 0.53615(15) 0.0165(5) Uani 1 1 d .
C7 C 0.2441(5) 0.60658(18) 0.65557(15) 0.0151(5) Uani 1 1 d .
C8 C 0.4797(5) 0.6021(2) 0.72016(17) 0.0193(5) Uani 1 1 d .
H8 H 0.5672 0.6612 0.7413 0.023 Uiso 1 1 calc R
C9 C 0.5867(5) 0.5122(2) 0.75368(17) 0.0210(5) Uani 1 1 d .
H9 H 0.7438 0.5109 0.7968 0.025 Uiso 1 1 calc R
C10 C 0.4568(5) 0.42366(19) 0.72213(17) 0.0205(5) Uani 1 1 d .
H10 H 0.5324 0.3628 0.7428 0.025 Uiso 1 1 calc R
C11 C 0.2141(5) 0.42555(19) 0.65972(16) 0.0181(5) Uani 1 1 d .
H11 H 0.1248 0.3663 0.6397 0.022 Uiso 1 1 calc R
C12 C 0.1066(5) 0.51684(18) 0.62757(16) 0.0167(5) Uani 1 1 d .
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
C12 O1 H1O 109.5
C6 N1 H1N 113.9
C6 N1 H2N 112.3
H1N N1 H2N 111.0
C2 C1 C6 122.3(2)
C2 C1 Br1 118.11(19)
C6 C1 Br1 119.58(19)
C3 C2 C1 119.3(2)
C3 C2 H2 120.4
C1 C2 H2 120.4
C2 C3 C4 119.1(2)
C2 C3 H3 120.4
C4 C3 H3 120.4
C5 C4 C3 121.7(2)
C5 C4 H4 119.1
C3 C4 H4 119.1
C4 C5 C6 119.2(2)
C4 C5 C7 121.7(2)
C6 C5 C7 119.1(2)
C1 C6 C5 118.2(2)
C1 C6 N1 121.3(2)
C5 C6 N1 120.4(2)
C8 C7 C12 118.0(2)
C8 C7 C5 123.0(2)
C12 C7 C5 118.9(2)
C9 C8 C7 121.8(2)
C9 C8 H8 119.1
C7 C8 H8 119.1
C8 C9 C10 119.2(2)
C8 C9 H9 120.4
C10 C9 H9 120.4
C9 C10 C11 120.5(2)
C9 C10 H10 119.8
C11 C10 H10 119.8
C12 C11 C10 119.5(2)
C12 C11 H11 120.3
C10 C11 H11 120.3
O1 C12 C11 121.8(2)
O1 C12 C7 117.3(2)
C11 C12 C7 120.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.909(3)
O1 C12 1.364(3)
O1 H1O 0.8199
N1 C6 1.408(3)
N1 H1N 0.8113
N1 H2N 0.8457
C1 C2 1.391(4)
C1 C6 1.396(3)
C2 C3 1.389(4)
C2 H2 0.9300
C3 C4 1.396(4)
C3 H3 0.9300
C4 C5 1.394(3)
C4 H4 0.9300
C5 C6 1.408(4)
C5 C7 1.497(3)
C7 C8 1.395(3)
C7 C12 1.402(3)
C8 C9 1.381(4)
C8 H8 0.9300
C9 C10 1.391(4)
C9 H9 0.9300
C10 C11 1.393(4)
C10 H10 0.9300
C11 C12 1.391(3)
C11 H11 0.9300
