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#$Date: 2025-08-20 17:12:52 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301832 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/41/4104110.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.
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data_4104110
loop_
_publ_author_name
'Jian-Hua Xie'
'Sheng Liu'
'Wei-Ling Kong'
'Wen-Ju Bai'
'Xiao-Chen Wang'
'Li-Xin Wang'
'Qi-Lin Zhou'
_publ_section_title
;
 Highly Enantioselective and Diastereoselective Synthesis of Chiral Amino
 Alcohols by Ruthenium-Catalyzed Asymmetric Hydrogenation of α-Amino
 Aliphatic Ketones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4222
_journal_page_last               4223
_journal_paper_doi               10.1021/ja901058u
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C13 H18 Br N O'
_chemical_formula_sum            'C13 H18 Br N O'
_chemical_formula_weight         284.19
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 99.744(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.1637(12)
_cell_length_b                   7.3171(8)
_cell_length_c                   10.0120(14)
_cell_measurement_reflns_used    1753
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      2.1
_cell_volume                     661.64(15)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_sigmaI/netI    0.0779
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6777
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    3.087
_exptl_absorpt_correction_T_max  0.7903
_exptl_absorpt_correction_T_min  0.5772
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
    ENTER TEXT OF LETTER 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
'Flack H D (1983), 1063 Friedel Pairs, Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.002(9)
_refine_ls_extinction_coef       0.0137(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.861
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2323
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.861
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0273
_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)+(0.0203P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0509
_refine_ls_wR_factor_ref         0.0594
_reflns_number_gt                1183
_reflns_number_total             2323
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja901058u_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               4104110
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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 0.98030(4) 0.76161(8) 0.58520(4) 0.0862(2) Uani 1 1 d .
O1 O 0.5442(3) 0.3087(3) 0.0324(2) 0.0510(8) Uani 1 1 d D
H1 H 0.563(4) 0.216(4) -0.008(4) 0.077 Uiso 1 1 d D
N1 N 0.3449(3) 0.5379(3) 0.1430(2) 0.0353(7) Uani 1 1 d .
C1 C 0.5855(4) 0.1079(5) 0.2273(3) 0.0549(11) Uani 1 1 d .
H1A H 0.5979 0.0018 0.1740 0.082 Uiso 1 1 calc R
H1B H 0.5449 0.0721 0.3057 0.082 Uiso 1 1 calc R
H1C H 0.6797 0.1656 0.2555 0.082 Uiso 1 1 calc R
C2 C 0.4805(3) 0.2414(6) 0.1428(3) 0.0413(9) Uani 1 1 d .
H2 H 0.3894 0.1756 0.1059 0.050 Uiso 1 1 calc R
C3 C 0.4393(3) 0.4032(4) 0.2258(3) 0.0347(9) Uani 1 1 d .
H3 H 0.3795 0.3528 0.2895 0.042 Uiso 1 1 calc R
C4 C 0.5716(3) 0.4932(4) 0.3114(3) 0.0307(8) Uani 1 1 d .
C5 C 0.6700(4) 0.5986(5) 0.2554(3) 0.0470(10) Uani 1 1 d .
H5 H 0.6551 0.6157 0.1620 0.056 Uiso 1 1 calc R
C6 C 0.7923(4) 0.6805(4) 0.3363(4) 0.0504(11) Uani 1 1 d .
H6 H 0.8580 0.7514 0.2972 0.060 Uiso 1 1 calc R
C7 C 0.8136(4) 0.6549(5) 0.4739(4) 0.0454(10) Uani 1 1 d .
C8 C 0.7178(4) 0.5503(5) 0.5337(3) 0.0466(10) Uani 1 1 d .
H8 H 0.7331 0.5330 0.6270 0.056 Uiso 1 1 calc R
C9 C 0.5975(4) 0.4714(4) 0.4508(4) 0.0420(10) Uani 1 1 d .
H9 H 0.5318 0.4011 0.4904 0.050 Uiso 1 1 calc R
C10 C 0.2901(3) 0.6797(4) 0.2282(3) 0.0466(10) Uani 1 1 d .
H10A H 0.3672 0.7676 0.2605 0.056 Uiso 1 1 calc R
H10B H 0.2559 0.6249 0.3056 0.056 Uiso 1 1 calc R
C11 C 0.1631(3) 0.7698(7) 0.1341(3) 0.0628(10) Uani 1 1 d .
H11A H 0.0870 0.8104 0.1839 0.075 Uiso 1 1 calc R
H11B H 0.1978 0.8739 0.0883 0.075 Uiso 1 1 calc R
C12 C 0.1048(4) 0.6222(6) 0.0342(4) 0.0791(15) Uani 1 1 d .
H12A H 0.1051 0.6637 -0.0578 0.095 Uiso 1 1 calc R
H12B H 0.0043 0.5899 0.0432 0.095 Uiso 1 1 calc R
C13 C 0.2071(3) 0.4583(5) 0.0666(4) 0.0507(10) Uani 1 1 d .
H13A H 0.1650 0.3696 0.1212 0.061 Uiso 1 1 calc R
H13B H 0.2256 0.3995 -0.0157 0.061 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'
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
C2 O1 H1 104(3)
C3 N1 C13 113.3(3)
C3 N1 C10 111.6(2)
C13 N1 C10 103.3(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
O1 C2 C1 110.5(3)
O1 C2 C3 109.0(3)
C1 C2 C3 112.7(2)
O1 C2 H2 108.2
C1 C2 H2 108.2
C3 C2 H2 108.2
N1 C3 C4 111.5(2)
N1 C3 C2 112.8(2)
C4 C3 C2 113.4(3)
N1 C3 H3 106.2
C4 C3 H3 106.2
C2 C3 H3 106.2
C5 C4 C9 117.6(3)
C5 C4 C3 122.1(3)
C9 C4 C3 120.3(3)
C4 C5 C6 121.3(3)
C4 C5 H5 119.4
C6 C5 H5 119.4
C7 C6 C5 119.1(3)
C7 C6 H6 120.4
C5 C6 H6 120.4
C6 C7 C8 121.3(3)
C6 C7 Br1 119.8(3)
C8 C7 Br1 118.8(3)
C7 C8 C9 118.2(3)
C7 C8 H8 120.9
C9 C8 H8 120.9
C4 C9 C8 122.5(3)
C4 C9 H9 118.7
C8 C9 H9 118.7
N1 C10 C11 104.2(3)
N1 C10 H10A 110.9
C11 C10 H10A 110.9
N1 C10 H10B 110.9
C11 C10 H10B 110.9
H10A C10 H10B 108.9
C12 C11 C10 104.4(3)
C12 C11 H11A 110.9
C10 C11 H11A 110.9
C12 C11 H11B 110.9
C10 C11 H11B 110.9
H11A C11 H11B 108.9
C11 C12 C13 106.7(3)
C11 C12 H12A 110.4
C13 C12 H12A 110.4
C11 C12 H12B 110.4
C13 C12 H12B 110.4
H12A C12 H12B 108.6
N1 C13 C12 103.9(3)
N1 C13 H13A 111.0
C12 C13 H13A 111.0
N1 C13 H13B 111.0
C12 C13 H13B 111.0
H13A C13 H13B 109.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C7 1.900(3)
O1 C2 1.423(4)
O1 H1 0.82(2)
N1 C3 1.471(4)
N1 C13 1.480(4)
N1 C10 1.483(4)
C1 C2 1.523(5)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 C3 1.530(5)
C2 H2 0.9800
C3 C4 1.512(4)
C3 H3 0.9800
C4 C5 1.376(4)
C4 C9 1.384(4)
C5 C6 1.401(4)
C5 H5 0.9300
C6 C7 1.371(4)
C6 H6 0.9300
C7 C8 1.376(4)
C8 C9 1.389(4)
C8 H8 0.9300
C9 H9 0.9300
C10 C11 1.519(4)
C10 H10A 0.9700
C10 H10B 0.9700
C11 C12 1.507(5)
C11 H11A 0.9700
C11 H11B 0.9700
C12 C13 1.523(5)
C12 H12A 0.9700
C12 H12B 0.9700
C13 H13A 0.9700
C13 H13B 0.9700
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.82(2) 2.15(3) 2.941(3) 161(4) 2_645
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
C13 N1 C3 C4 -174.9(3)
C10 N1 C3 C4 -58.8(4)
C13 N1 C3 C2 56.1(4)
C10 N1 C3 C2 172.3(3)
O1 C2 C3 N1 53.6(3)
C1 C2 C3 N1 176.6(3)
O1 C2 C3 C4 -74.3(3)
C1 C2 C3 C4 48.7(4)
N1 C3 C4 C5 -56.4(4)
C2 C3 C4 C5 72.2(4)
N1 C3 C4 C9 123.6(3)
C2 C3 C4 C9 -107.7(3)
C9 C4 C5 C6 0.1(5)
C3 C4 C5 C6 -179.8(3)
C4 C5 C6 C7 -0.1(5)
C5 C6 C7 C8 0.1(5)
C5 C6 C7 Br1 179.0(2)
C6 C7 C8 C9 -0.3(5)
Br1 C7 C8 C9 -179.2(3)
C5 C4 C9 C8 -0.3(5)
C3 C4 C9 C8 179.6(3)
C7 C8 C9 C4 0.4(5)
C3 N1 C10 C11 -163.9(3)
C13 N1 C10 C11 -41.8(3)
N1 C10 C11 C12 28.2(4)
C10 C11 C12 C13 -4.5(4)
C3 N1 C13 C12 159.4(3)
C10 N1 C13 C12 38.5(4)
C11 C12 C13 N1 -20.8(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102507523
