#------------------------------------------------------------------------------
#$Date: 2016-03-22 10:39:23 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178879 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/08/4110863.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_4110863
loop_
_publ_author_name
'Guo-Hua Hou'
'Jian-Hua Xie'
'Li-Xin Wang'
'Qi-Lin Zhou'
_publ_section_title
;
 Highly Efficient Rh(I)-Catalyzed Asymmetric Hydrogenation of Enamines
 Using Monodente Spiro Phosphonite Ligands
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11774
_journal_page_last               11775
_journal_paper_doi               10.1021/ja0644778
_journal_volume                  128
_journal_year                    2006
_chemical_formula_moiety         'C18 H21 Br1.35 Cl0.65 N'
_chemical_formula_sum            'C18 H21 Br1.35 Cl0.65 N'
_chemical_formula_weight         382.28
_chemical_name_systematic
; 
 ? 
;
_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                 90.373(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.5800(14)
_cell_length_b                   6.9147(11)
_cell_length_c                   14.765(3)
_cell_measurement_reflns_used    2713
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.1
_cell_measurement_theta_min      1.4
_cell_volume                     876.0(3)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0748
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8286
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         1.38
_exptl_absorpt_coefficient_mu    3.238
_exptl_absorpt_correction_T_max  0.8814
_exptl_absorpt_correction_T_min  0.7378
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       prism
_exptl_crystal_F_000             389
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.028(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.861
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         3739
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      0.906
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0330
_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)+(0.0235P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0603
_refine_ls_wR_factor_ref         0.0646
_reflns_number_gt                2457
_reflns_number_total             3739
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0644778si20060623_111244.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        876.0(2)
_cod_database_code               4110863
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.53732(4) 1.12316(6) 0.11730(2) 0.05656(15) Uani 1 1 d . . .
Cl1 Cl 0.18456(8) 0.10429(11) 0.39633(4) 0.0591(3) Uani 0.652(2) 1 d P . .
Br2 Br 0.18456(8) 0.10429(11) 0.39633(4) 0.0591(3) Uani 0.348(2) 1 d P . .
N1 N 0.1995(3) 0.5382(5) 0.36210(18) 0.0369(8) Uani 1 1 d D A .
C1 C 0.0838(3) 0.6349(7) 0.30040(17) 0.0310(7) Uani 1 1 d D . .
H1A H 0.0981 0.7713 0.3095 0.037 Uiso 0.453(18) 1 d PR A 1
H1B H 0.1015 0.7720 0.3001 0.037 Uiso 0.547(18) 1 d PR A 2
C2 C -0.0850(3) 0.5895(6) 0.3291(2) 0.0353(9) Uani 1 1 d . A .
H2A H -0.1082 0.4513 0.3178 0.042 Uiso 1 1 calc R . .
H2B H -0.0972 0.6146 0.3947 0.042 Uiso 1 1 calc R . .
C3 C -0.1974(4) 0.7148(5) 0.2757(2) 0.0329(9) Uani 1 1 d . . .
C4 C -0.2060(4) 0.9116(5) 0.2955(2) 0.0403(9) Uani 1 1 d . A .
H4A H -0.1408 0.9642 0.3416 0.048 Uiso 1 1 calc R . .
C5 C -0.3084(4) 1.0321(5) 0.2490(2) 0.0422(10) Uani 1 1 d . . .
H5A H -0.3160 1.1654 0.2640 0.051 Uiso 1 1 calc R A .
C6 C -0.3986(4) 0.9546(6) 0.1809(2) 0.0387(9) Uani 1 1 d . A .
C7 C -0.3917(4) 0.7640(5) 0.1585(2) 0.0390(9) Uani 1 1 d . . .
H7A H -0.4548 0.7145 0.1108 0.047 Uiso 1 1 calc R A .
C8 C -0.2902(3) 0.6408(7) 0.2065(2) 0.0368(8) Uani 1 1 d . A .
H8A H -0.2852 0.5073 0.1916 0.044 Uiso 1 1 calc R . .
C15 C 0.1865(3) 0.6023(8) 0.46035(18) 0.0429(8) Uani 1 1 d D . .
H15A H 0.1253 0.5117 0.4942 0.051 Uiso 0.528(14) 1 d PR A 1
H15B H 0.1376 0.7270 0.4630 0.051 Uiso 0.528(14) 1 d PR A 1
H15C H 0.1067 0.5307 0.4910 0.051 Uiso 0.472(14) 1 d PR A 2
H15D H 0.1638 0.7380 0.4639 0.051 Uiso 0.472(14) 1 d PR A 2
C18 C 0.3667(3) 0.5695(6) 0.3333(2) 0.0455(11) Uani 1 1 d D . .
H18A H 0.3837 0.6999 0.3133 0.055 Uiso 0.528(14) 1 d PR A 1
H18B H 0.3944 0.4815 0.2857 0.055 Uiso 0.528(14) 1 d PR A 1
H18C H 0.3728 0.6769 0.2922 0.055 Uiso 0.472(14) 1 d PR A 2
H18D H 0.4055 0.4561 0.3034 0.055 Uiso 0.472(14) 1 d PR A 2
C9 C 0.122(3) 0.602(3) 0.2011(7) 0.025(2) Uani 0.453(18) 1 d PGDU A 1
C10 C 0.166(3) 0.750(2) 0.1430(10) 0.037(2) Uani 0.453(18) 1 d PG A 1
H10A H 0.1801 0.8770 0.1657 0.045 Uiso 0.453(18) 1 calc PR A 1
C11 C 0.189(3) 0.711(2) 0.0516(9) 0.054(3) Uani 0.453(18) 1 d PG A 1
H11A H 0.2191 0.8127 0.0119 0.065 Uiso 0.453(18) 1 calc PR A 1
C12 C 0.168(3) 0.525(2) 0.0184(6) 0.058(4) Uani 0.453(18) 1 d PG A 1
H12A H 0.1839 0.4990 -0.0440 0.069 Uiso 0.453(18) 1 calc PR A 1
C13 C 0.124(3) 0.3770(19) 0.0765(9) 0.051(3) Uani 0.453(18) 1 d PG A 1
H13A H 0.1097 0.2497 0.0538 0.061 Uiso 0.453(18) 1 calc PR A 1
C14 C 0.101(3) 0.415(2) 0.1678(8) 0.036(2) Uani 0.453(18) 1 d PG A 1
H14A H 0.0707 0.3140 0.2075 0.043 Uiso 0.453(18) 1 calc PR A 1
C16 C 0.3556(9) 0.627(3) 0.4946(5) 0.074(4) Uani 0.528(14) 1 d PD A 1
H16A H 0.3708 0.5612 0.5536 0.088 Uiso 0.528(14) 1 calc PR A 1
H16B H 0.3824 0.7652 0.5014 0.088 Uiso 0.528(14) 1 calc PR A 1
C17 C 0.4563(9) 0.530(2) 0.4198(5) 0.057(3) Uani 0.528(14) 1 d PD A 1
H17A H 0.5615 0.5886 0.4176 0.068 Uiso 0.528(14) 1 calc PR A 1
H17B H 0.4667 0.3894 0.4305 0.068 Uiso 0.528(14) 1 calc PR A 1
C9' C 0.103(2) 0.557(2) 0.2048(6) 0.025(2) Uani 0.547(18) 1 d PGD A 2
C10' C 0.151(3) 0.6914(19) 0.1407(8) 0.037(2) Uani 0.547(18) 1 d PG A 2
H10B H 0.1668 0.8224 0.1576 0.045 Uiso 0.547(18) 1 calc PR A 2
C11' C 0.175(3) 0.634(2) 0.0516(7) 0.054(3) Uani 0.547(18) 1 d PG A 2
H11B H 0.2076 0.7257 0.0078 0.065 Uiso 0.547(18) 1 calc PR A 2
C12' C 0.152(2) 0.442(2) 0.0268(6) 0.058(4) Uani 0.547(18) 1 d PG A 2
H12B H 0.1684 0.4028 -0.0340 0.069 Uiso 0.547(18) 1 calc PR A 2
C13' C 0.104(2) 0.3078(19) 0.0910(8) 0.051(3) Uani 0.547(18) 1 d PG A 2
H13B H 0.0884 0.1767 0.0740 0.061 Uiso 0.547(18) 1 calc PR A 2
C14' C 0.080(3) 0.3652(19) 0.1800(7) 0.036(2) Uani 0.547(18) 1 d PG A 2
H14B H 0.0476 0.2735 0.2239 0.043 Uiso 0.547(18) 1 calc PR A 2
C16' C 0.3524(10) 0.562(3) 0.4967(5) 0.074(4) Uani 0.472(14) 1 d PD A 2
H16C H 0.3675 0.4223 0.5092 0.088 Uiso 0.472(14) 1 calc PR A 2
H16D H 0.3737 0.6363 0.5527 0.088 Uiso 0.472(14) 1 calc PR A 2
C17' C 0.4582(10) 0.631(2) 0.4175(6) 0.057(3) Uani 0.472(14) 1 d PD A 2
H17C H 0.4731 0.7727 0.4191 0.068 Uiso 0.472(14) 1 calc PR A 2
H17D H 0.5614 0.5668 0.4199 0.068 Uiso 0.472(14) 1 calc PR A 2
H1 H 0.175(3) 0.389(5) 0.364(2) 0.046(10) Uiso 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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C18 112.9(2)
C1 N1 C15 113.4(2)
C18 N1 C15 107.6(2)
N1 C1 C9' 109.2(8)
N1 C1 C9 111.9(10)
C9' C1 C9 13.2(10)
N1 C1 C2 111.2(3)
C9' C1 C2 107.0(8)
C9 C1 C2 116.2(9)
C3 C2 C1 109.6(3)
C8 C3 C4 118.9(3)
C8 C3 C2 122.1(4)
C4 C3 C2 119.0(3)
C5 C4 C3 121.1(3)
C6 C5 C4 118.6(3)
C7 C6 C5 122.1(3)
C7 C6 Br1 120.0(3)
C5 C6 Br1 117.9(3)
C6 C7 C8 119.5(3)
C3 C8 C7 119.8(4)
N1 C15 C16 105.6(4)
N1 C15 C16' 101.9(5)
C16 C15 C16' 16.8(14)
C17 C18 N1 102.4(4)
C17 C18 C17' 26.5(6)
N1 C18 C17' 107.1(4)
C10 C9 C14 120.0
C10 C9 C1 122.9(10)
C14 C9 C1 116.9(10)
C11 C10 C9 120.0
C10 C11 C12 120.0
C13 C12 C11 120.0
C14 C13 C12 120.0
C13 C14 C9 120.0
C15 C16 C17 104.2(7)
C18 C17 C16 103.9(6)
C10' C9' C14' 120.0
C10' C9' C1 115.5(8)
C14' C9' C1 124.5(8)
C11' C10' C9' 120.0
C10' C11' C12' 120.0
C11' C12' C13' 120.0
C14' C13' C12' 120.0
C13' C14' C9' 120.0
C15 C16' C17' 102.9(7)
C18 C17' C16' 103.1(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C6 1.908(3)
N1 C1 1.501(4)
N1 C18 1.514(4)
N1 C15 1.522(4)
C1 C9' 1.521(7)
C1 C9 1.522(8)
C1 C2 1.544(4)
C2 C3 1.514(4)
C3 C8 1.390(4)
C3 C4 1.394(4)
C4 C5 1.390(4)
C5 C6 1.374(4)
C6 C7 1.360(5)
C7 C8 1.406(5)
C15 C16 1.542(8)
C15 C16' 1.544(9)
C18 C17 1.511(7)
C18 C17' 1.526(8)
C9 C10 1.3900
C9 C14 1.3900
C10 C11 1.3900
C11 C12 1.3900
C12 C13 1.3900
C13 C14 1.3900
C16 C17 1.557(9)
C9' C10' 1.3900
C9' C14' 1.3900
C10' C11' 1.3900
C11' C12' 1.3900
C12' C13' 1.3900
C13' C14' 1.3900
C16' C17' 1.561(10)
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
N1 H1 Cl1 1.05(3) 2.03(3) 3.045(3) 161(3)
N1 H1 Br2 1.05(3) 2.03(3) 3.045(3) 161(3)
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
C18 N1 C1 C9' 58.9(7)
C15 N1 C1 C9' -178.4(7)
C18 N1 C1 C9 45.1(8)
C15 N1 C1 C9 167.8(8)
C18 N1 C1 C2 176.7(3)
C15 N1 C1 C2 -60.6(4)
N1 C1 C2 C3 170.6(3)
C9' C1 C2 C3 -70.2(8)
C9 C1 C2 C3 -60.0(10)
C1 C2 C3 C8 106.6(4)
C1 C2 C3 C4 -72.2(4)
C8 C3 C4 C5 1.8(5)
C2 C3 C4 C5 -179.4(3)
C3 C4 C5 C6 -1.8(5)
C4 C5 C6 C7 0.7(5)
C4 C5 C6 Br1 -179.6(3)
C5 C6 C7 C8 0.4(5)
Br1 C6 C7 C8 -179.3(2)
C4 C3 C8 C7 -0.6(5)
C2 C3 C8 C7 -179.4(3)
C6 C7 C8 C3 -0.5(5)
C1 N1 C15 C16 -138.3(9)
C18 N1 C15 C16 -12.7(9)
C1 N1 C15 C16' -155.2(9)
C18 N1 C15 C16' -29.6(9)
C1 N1 C18 C17 159.2(6)
C15 N1 C18 C17 33.4(7)
C1 N1 C18 C17' 132.2(7)
C15 N1 C18 C17' 6.3(8)
N1 C1 C9 C10 -114.2(14)
C9' C1 C9 C10 165(9)
C2 C1 C9 C10 116.8(14)
N1 C1 C9 C14 69.9(14)
C9' C1 C9 C14 -11(7)
C2 C1 C9 C14 -59.1(15)
C14 C9 C10 C11 0.0
C1 C9 C10 C11 -176(2)
C9 C10 C11 C12 0.0
C10 C11 C12 C13 0.0
C11 C12 C13 C14 0.0
C12 C13 C14 C9 0.0
C10 C9 C14 C13 0.0
C1 C9 C14 C13 176.0(19)
N1 C15 C16 C17 -12.4(14)
C16' C15 C16 C17 66.8(19)
N1 C18 C17 C16 -40.5(12)
C17' C18 C17 C16 63.0(13)
C15 C16 C17 C18 33.1(16)
N1 C1 C9' C10' -116.1(10)
C9 C1 C9' C10' -12(7)
C2 C1 C9' C10' 123.6(10)
N1 C1 C9' C14' 62.6(13)
C9 C1 C9' C14' 167(9)
C2 C1 C9' C14' -57.7(13)
C14' C9' C10' C11' 0.0
C1 C9' C10' C11' 178.8(15)
C9' C10' C11' C12' 0.0
C10' C11' C12' C13' 0.0
C11' C12' C13' C14' 0.0
C12' C13' C14' C9' 0.0
C10' C9' C14' C13' 0.0
C1 C9' C14' C13' -178.6(17)
N1 C15 C16' C17' 41.1(15)
C16 C15 C16' C17' -63.7(18)
C17 C18 C17' C16' -64.0(12)
N1 C18 C17' C16' 19.4(14)
C15 C16' C17' C18 -37.6(17)
