Organocatalytic asymmetric synthesis of benzazepinoindole derivatives with trifluoromethylated quaternary stereocenters by chiral phosphoric acid catalysts.
Rahman, Abdul; Xie, En; Lin, Xufeng; Organic & biomolecular chemistry 16 (2018) 1367–1374; doi:10.1039/c8ob00055g

data_7156084
_publ_section_title
;
 Organocatalytic asymmetric synthesis of benzazepinoindole derivatives
 with trifluoromethylated quaternary stereocenters by chiral phosphoric
 acid catalysts.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1367
_journal_page_last               1374
_journal_paper_doi               10.1039/c8ob00055g
_journal_volume                  16
_journal_year                    2018
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C26 H19 Cl F3 N3'
_chemical_formula_sum            'C26 H19 Cl F3 N3'
_chemical_formula_weight         465.89
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2017-03-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2018-01-03 deposited with the CCDC.
2018-01-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.523(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.4760(7)
_cell_length_b                   10.3255(9)
_cell_length_c                   12.5157(12)
_cell_measurement_reflns_used    2996
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5921
_cell_measurement_theta_min      3.2042
_cell_volume                     1476.2(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
  1 omega  -86.00   14.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.7183  -38.0000  147.0000 100

  2 omega  -41.00    6.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.7183  110.0000  -20.0000 47

  3 omega  -26.00   43.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.7183   38.0000  -30.0000 69

  4 omega  -87.00   15.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.7183  -77.0000   60.0000 102
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0509702000
_diffrn_orient_matrix_UB_12      0.0251103000
_diffrn_orient_matrix_UB_13      -0.0202636000
_diffrn_orient_matrix_UB_21      -0.0134720000
_diffrn_orient_matrix_UB_22      0.0623239000
_diffrn_orient_matrix_UB_23      0.0192368000
_diffrn_orient_matrix_UB_31      0.0328928000
_diffrn_orient_matrix_UB_32      -0.0137951000
_diffrn_orient_matrix_UB_33      0.0496605000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10501
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_min         3.211
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.048
_exptl_crystal_description       needle
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 1228 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         5349
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.939
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0427P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.1035
_reflns_Friedel_coverage         0.887
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                3713
_reflns_number_total             5349
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00055g2.cif
_cod_data_source_block           170309_ar_875_122_05_sq
_cod_depositor_comments          'Adding full bibliography for 7156084.cif.'
_cod_database_code               7156084
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c10 h10 n2 o8 F1 Cl1'
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.926
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H,H) groups
2. Restrained distances
 N2-H2
 0.86 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C1(H1A), C3(H3A), C4(H4), C12(H12), C13(H13), C14(H14),
 C15(H15), C19(H19), C22(H22), C24(H24), C25(H25)
3.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_shelx_res_checksum              36933
_shelx_fab_checksum              23291
_olex2_submission_special_instructions 'No special instructions were received'