Enantioselective Dearomative Arylation of Isoquinolines
Zhang, Ming; Sun, Wangsheng; Zhu, Gongming; Bao, Guangjun; Zhang, Bangzhi; Hong, Liang; Li, Min; Wang, Rui; ACS Catalysis 6 (2016) 5290–; doi:10.1021/acscatal.6b01693

data_4516699
_publ_section_title
;
 Enantioselective Dearomative Arylation of Isoquinolines
;
_journal_issue                   8
_journal_name_full               'ACS Catalysis'
_journal_page_first              5290
_journal_paper_doi               10.1021/acscatal.6b01693
_journal_volume                  6
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C22 H21 Cl N2 O2'
_chemical_formula_sum            'C23 H21 Cl N O2'
_chemical_formula_weight         378.86
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-01-07
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5413(5)
_cell_length_b                   12.5331(12)
_cell_length_c                   16.6646(14)
_cell_measurement_reflns_used    1028
_cell_measurement_temperature    295.14(10)
_cell_measurement_theta_max      21.4000
_cell_measurement_theta_min      4.0610
_cell_volume                     1992.8(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.14(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega   35.00   87.80   1.2000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       20.4291  178.0000   90.0000 44

  2 omega  -20.00   58.00   1.2000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       20.4291  -99.0000 -120.0000 65

  3 omega   64.00   90.40   1.2000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       20.4291   19.0000  -60.0000 22
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0166418000
_diffrn_orient_matrix_UB_12      0.0463011000
_diffrn_orient_matrix_UB_13      0.0225219000
_diffrn_orient_matrix_UB_21      -0.0714643000
_diffrn_orient_matrix_UB_22      0.0054111000
_diffrn_orient_matrix_UB_23      0.0110584000
_diffrn_orient_matrix_UB_31      0.0118578000
_diffrn_orient_matrix_UB_32      -0.0320925000
_diffrn_orient_matrix_UB_33      0.0343896000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.1076
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5681
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.019
_diffrn_reflns_theta_min         3.473
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74566
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_description       block
_exptl_crystal_F_000             796
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 409 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3700
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1522
_refine_ls_R_factor_gt           0.0734
_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^)+(0.0540P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1892
_reflns_Friedel_coverage         0.655
_reflns_Friedel_fraction_full    0.881
_reflns_Friedel_fraction_max     0.869
_reflns_number_gt                1782
_reflns_number_total             3700
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b01693_si_002.cif
_cod_data_source_block           zhangm0104
_cod_database_code               4516699
_reflns_odcompleteness_completeness 99.53
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), N2(H2), C14(H14),
 C15(H15), C17(H17)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-01-06
_olex2_submission_special_instructions 'No special instructions were received'