#------------------------------------------------------------------------------
#$Date: 2016-03-22 13:49:12 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178979 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/02/4120290.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_4120290
loop_
_publ_author_name
'Kodai Saito'
'Yukihiro Shibata'
'Masahiro Yamanaka'
'Takahiko Akiyama'
_publ_section_title
;
 Chiral Phosphoric Acid-Catalyzed Oxidative Kinetic Resolution of
 Indolines Based on Transfer Hydrogenation to Imines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11740
_journal_page_last               11743
_journal_paper_doi               10.1021/ja406004q
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C16 H14 Br N O'
_chemical_formula_weight         316.19
_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                   8.539(3)
_cell_length_b                   9.408(3)
_cell_length_c                   17.039(5)
_cell_measurement_reflns_used    1663
_cell_measurement_temperature    123
_cell_measurement_theta_max      27.23
_cell_measurement_theta_min      2.47
_cell_volume                     1368.8(8)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_sigmaI/netI    0.0947
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3900
_diffrn_reflns_theta_full        27.71
_diffrn_reflns_theta_max         27.71
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    2.994
_exptl_absorpt_correction_T_max  0.7539
_exptl_absorpt_correction_T_min  0.5858
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.846
_refine_diff_density_min         -1.417
_refine_diff_density_rms         0.104
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.004(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2941
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.955
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0322P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1010
_reflns_number_gt                2503
_reflns_number_total             2941
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja406004q_si_005.cif
_cod_data_source_block           shelxla
_cod_original_cell_volume        1368.8(7)
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4120290
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
Br1 Br 0.08374(5) 0.52419(5) 1.03813(2) 0.02733(14) Uani 1 1 d .
C1 C 0.7051(5) 0.3009(5) 0.8464(2) 0.0208(9) Uani 1 1 d .
H1 H 0.6075 0.2534 0.8654 0.025 Uiso 1 1 calc R
C2 C 0.8232(5) 0.1900(5) 0.8179(3) 0.0255(10) Uani 1 1 d .
H2A H 0.9064 0.1743 0.8575 0.031 Uiso 1 1 calc R
H2B H 0.7709 0.0983 0.8066 0.031 Uiso 1 1 calc R
C3 C 0.8889(5) 0.2546(5) 0.7446(2) 0.0227(10) Uani 1 1 d .
C4 C 1.0189(5) 0.2160(5) 0.7011(3) 0.0290(11) Uani 1 1 d .
H4 H 1.0845 0.1403 0.7179 0.035 Uiso 1 1 calc R
C5 C 1.0519(5) 0.2888(6) 0.6334(3) 0.0313(12) Uani 1 1 d .
H5 H 1.1417 0.2635 0.6035 0.038 Uiso 1 1 calc R
C6 C 0.9570(5) 0.3981(5) 0.6077(3) 0.0268(11) Uani 1 1 d .
H6 H 0.9813 0.4457 0.5601 0.032 Uiso 1 1 calc R
C7 C 0.8256(5) 0.4396(5) 0.6509(2) 0.0219(10) Uani 1 1 d .
H7 H 0.7597 0.5148 0.6337 0.026 Uiso 1 1 calc R
C8 C 0.7958(5) 0.3667(5) 0.7195(2) 0.0203(9) Uani 1 1 d .
C9 C 0.7732(5) 0.3948(5) 0.9103(3) 0.0282(11) Uani 1 1 d .
H9A H 0.8671 0.4427 0.8904 0.042 Uiso 1 1 calc R
H9B H 0.8009 0.3364 0.9558 0.042 Uiso 1 1 calc R
H9C H 0.6955 0.4661 0.9259 0.042 Uiso 1 1 calc R
C10 C 0.5537(4) 0.4818(5) 0.7666(2) 0.0194(9) Uani 1 1 d .
C11 C 0.4350(5) 0.4887(5) 0.8315(2) 0.0208(9) Uani 1 1 d .
C12 C 0.3397(5) 0.3726(5) 0.8506(3) 0.0231(10) Uani 1 1 d .
H12 H 0.3496 0.2850 0.8233 0.028 Uiso 1 1 calc R
C13 C 0.2306(5) 0.3883(5) 0.9103(3) 0.0234(10) Uani 1 1 d .
H13 H 0.1620 0.3120 0.9227 0.028 Uiso 1 1 calc R
C14 C 0.2211(4) 0.5113(5) 0.9508(2) 0.0215(9) Uani 1 1 d .
C15 C 0.3108(5) 0.6282(5) 0.9316(2) 0.0204(9) Uani 1 1 d .
H15 H 0.2991 0.7152 0.9592 0.025 Uiso 1 1 calc R
C16 C 0.4189(6) 0.6158(4) 0.8708(2) 0.0222(9) Uani 1 1 d .
H16 H 0.4815 0.6950 0.8564 0.027 Uiso 1 1 calc R
N1 N 0.6718(4) 0.3856(4) 0.77447(19) 0.0190(8) Uani 1 1 d .
O1 O 0.5429(3) 0.5616(4) 0.71008(17) 0.0281(7) 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'
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
N1 C1 C9 110.6(4)
N1 C1 C2 103.3(3)
C9 C1 C2 111.8(4)
N1 C1 H1 110.3
C9 C1 H1 110.3
C2 C1 H1 110.3
C3 C2 C1 103.6(4)
C3 C2 H2A 111.0
C1 C2 H2A 111.0
C3 C2 H2B 111.0
C1 C2 H2B 111.0
H2A C2 H2B 109.0
C4 C3 C8 119.6(4)
C4 C3 C2 129.9(4)
C8 C3 C2 110.5(4)
C5 C4 C3 119.0(5)
C5 C4 H4 120.5
C3 C4 H4 120.5
C4 C5 C6 121.2(4)
C4 C5 H5 119.4
C6 C5 H5 119.4
C5 C6 C7 120.9(4)
C5 C6 H6 119.6
C7 C6 H6 119.6
C8 C7 C6 117.1(4)
C8 C7 H7 121.5
C6 C7 H7 121.5
C7 C8 C3 122.3(4)
C7 C8 N1 129.2(4)
C3 C8 N1 108.5(4)
C1 C9 H9A 109.5
C1 C9 H9B 109.5
H9A C9 H9B 109.5
C1 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
O1 C10 N1 122.8(4)
O1 C10 C11 120.1(4)
N1 C10 C11 117.1(4)
C16 C11 C12 120.3(4)
C16 C11 C10 117.6(4)
C12 C11 C10 122.0(4)
C13 C12 C11 118.6(4)
C13 C12 H12 120.7
C11 C12 H12 120.7
C14 C13 C12 120.5(4)
C14 C13 H13 119.8
C12 C13 H13 119.8
C13 C14 C15 121.9(4)
C13 C14 Br1 119.6(3)
C15 C14 Br1 118.6(3)
C14 C15 C16 118.6(4)
C14 C15 H15 120.7
C16 C15 H15 120.7
C11 C16 C15 120.1(4)
C11 C16 H16 120.0
C15 C16 H16 120.0
C10 N1 C8 124.6(4)
C10 N1 C1 125.4(3)
C8 N1 C1 109.4(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C14 1.898(4)
C1 N1 1.489(5)
C1 C9 1.518(6)
C1 C2 1.530(6)
C1 H1 1.0000
C2 C3 1.499(6)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.384(6)
C3 C8 1.388(6)
C4 C5 1.371(7)
C4 H4 0.9500
C5 C6 1.381(7)
C5 H5 0.9500
C6 C7 1.397(6)
C6 H6 0.9500
C7 C8 1.379(6)
C7 H7 0.9500
C8 N1 1.426(5)
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 O1 1.224(5)
C10 N1 1.362(5)
C10 C11 1.502(5)
C11 C16 1.377(6)
C11 C12 1.401(6)
C12 C13 1.387(6)
C12 H12 0.9500
C13 C14 1.350(6)
C13 H13 0.9500
C14 C15 1.380(6)
C15 C16 1.392(6)
C15 H15 0.9500
C16 H16 0.9500
