A Frustrated Lewis Pair Catalyzed Asymmetric Transfer Hydrogenation of Imines Using Ammonia Borane.
Li, Songlei; Li, Gen; Meng, Wei; Du, Haifeng; Journal of the American Chemical Society 138 (2016) 12956–12962; doi:10.1021/jacs.6b07245

data_4130827
_publ_section_title
;
 A Frustrated Lewis Pair Catalyzed Asymmetric Transfer Hydrogenation of
 Imines Using Ammonia Borane.
;
_journal_issue                   39
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12956
_journal_page_last               12962
_journal_paper_doi               10.1021/jacs.6b07245
_journal_volume                  138
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H20 B2 F20 N2 O2 S2, C4 H8 O'
_chemical_formula_sum            'C36 H28 B2 F20 N2 O3 S2'
_chemical_formula_weight         1002.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-12-16
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.670(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.608(4)
_cell_length_b                   10.590(2)
_cell_length_c                   20.591(5)
_cell_measurement_reflns_used    6386
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4732
_cell_measurement_theta_min      2.2192
_cell_volume                     4011.3(15)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 45.1204
	          2theta: -20.0832
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 45.1204
	          2theta: -20.0832
scan:
	Number of images: 328
	           Slice: -110.0000 - 54.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 45.1204
	          2theta: -20.0832
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0334
_diffrn_orient_matrix_UB_12      0.0362
_diffrn_orient_matrix_UB_13      -0.0230
_diffrn_orient_matrix_UB_21      -0.0408
_diffrn_orient_matrix_UB_22      -0.0692
_diffrn_orient_matrix_UB_23      -0.0497
_diffrn_orient_matrix_UB_31      -0.0366
_diffrn_orient_matrix_UB_32      -0.0019
_diffrn_orient_matrix_UB_33      0.0327
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            22657
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_min         3.002
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_description       block
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 3504 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     638
_refine_ls_number_reflns         9075
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0474P)^2^+2.2001P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1008
_reflns_Friedel_coverage         0.879
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                8716
_reflns_number_total             9075
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b07245_si_002.cif
_cod_data_source_block           sa4481
_cod_original_cell_volume        4011.1(16)
_cod_database_code               4130827
_diffrn_number_total             4834
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C34A)=Sof(H34C)=Sof(H34D)=Sof(C35A)=Sof(H35C)=Sof(H35D)=Sof(O3A)=
 Sof(C36A)=Sof(H36C)=Sof(H36D)=Sof(C33A)=Sof(H33C)=Sof(H33D)=1-FVAR(1)
 Sof(O3)=Sof(C33)=Sof(H33A)=Sof(H33B)=Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(C35)=
 Sof(H35A)=Sof(H35B)=Sof(C34)=Sof(H34A)=Sof(H34B)=FVAR(1)
3.a Riding coordinates:
 N1(H1), N2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B), C34A(H34C,H34D), C35A(H35C,H35D), C36(H36A,H36B), C36A(H36C,
 H36D), C35(H35A,H35B), C34(H34A,H34B), C33A(H33C,H33D)
3.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C30(H30A,H30B,
 H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C)
;
_shelx_res_checksum              28001
_shelx_hkl_checksum              11353
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'