Catalytic enantioselective and regioselective substitution of 2,3-indolyldimethanols with enaminones
Lu, Yi-Nan; Ma, Chun; Lan, Jin-Ping; Zhu, Caiqiang; Mao, Yu-Jia; Mei, Guang-Jian; Zhang, Shu; Shi, Feng; Organic Chemistry Frontiers 5 (2018) 2657–; doi:10.1039/C8QO00565F

data_1554369
_publ_section_title
;
 Catalytic enantioselective and regioselective substitution of
 2,3-indolyldimethanols with enaminones
;
_journal_issue                   18
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2657
_journal_paper_doi               10.1039/C8QO00565F
_journal_volume                  5
_journal_year                    2018
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C43 H37 Cl3 N2 O2'
_chemical_formula_sum            'C43 H37 Cl3 N2 O2'
_chemical_formula_weight         720.09
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-12-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-06-07 deposited with the CCDC.
2018-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.306(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.757(9)
_cell_length_b                   12.558(10)
_cell_length_c                   14.389(12)
_cell_measurement_reflns_used    3289
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.899
_cell_measurement_theta_min      2.513
_cell_volume                     1918(3)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0729
_diffrn_reflns_av_unetI/netI     0.0920
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13691
_diffrn_reflns_point_group_measured_fraction_full 0.853
_diffrn_reflns_point_group_measured_fraction_max 0.785
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.097
_diffrn_reflns_theta_min         2.165
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1230 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     454
_refine_ls_number_reflns         7336
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.1189
_refine_ls_R_factor_gt           0.0663
_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^)+(0.0759P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1372
_refine_ls_wR_factor_ref         0.1587
_reflns_Friedel_coverage         0.591
_reflns_Friedel_fraction_full    0.700
_reflns_Friedel_fraction_max     0.611
_reflns_number_gt                4523
_reflns_number_total             7336
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00565f2.cif
_cod_data_source_block           sf_20171214_lyn_0m
_cod_database_code               1554369
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.897
_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) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2B,H2C), C4(H4A,H4B), C37(H37A,H37B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2A), C11(H11), C12(H12), C13(H13), C14(H14), C18(H18), C19(H19),
 C21(H21), C22(H22), C24(H24), C25(H25), C27(H27), C28(H28), C30(H30), C31(H31),
  C33(H33), C34(H34), C39(H39), C40(H40), C41(H41), C42(H42), C43(H43)
2.d Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C), C36(H36A,H36B,H36C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              90292
_shelx_hkl_checksum              18299
_olex2_submission_special_instructions 'No special instructions were received'