Oxidative Organocatalysed Enantioselective Coupling of Indoles with Aldehydes that Forms Quaternary Carbon Stereocentres
Rezayee, Nomaan Mohammed; Lauridsen, Vibeke Henriette; Næsborg, Line; Nguyen, Thanh V. Q.; Tobiesen, Henriette Natorp; Jorgensen, Karl Anker; Chemical Science  (2019) –; doi:10.1039/C9SC00196D

data_1550596
_publ_section_title
;
 Oxidative Organocatalysed Enantioselective Coupling of Indoles with
 Aldehydes that Forms Quaternary Carbon Stereocentres
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC00196D
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H18 Br N O2'
_chemical_formula_sum            'C22 H18 Br N O2'
_chemical_formula_weight         408.28
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-07-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-08-21 deposited with the CCDC.
2019-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3465(7)
_cell_length_b                   10.4901(8)
_cell_length_c                   18.9441(15)
_cell_measurement_reflns_used    9601
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.838
_cell_measurement_theta_min      2.286
_cell_volume                     1857.4(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56086
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            84357
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         24.739
_diffrn_reflns_theta_min         1.697
_exptl_absorpt_coefficient_mu    1.200
_exptl_absorpt_correction_T_max  0.7240
_exptl_absorpt_correction_T_min  0.6584
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1006 before and 0.0646 after correction.
The Ratio of minimum to maximum transmission is 0.9094.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear orangish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.372
_exptl_crystal_size_min          0.224
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 2540 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         6463
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0237
_refine_ls_R_factor_gt           0.0209
_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^)+(0.0238P)^2^+0.2070P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0493
_refine_ls_wR_factor_ref         0.0500
_reflns_Friedel_coverage         0.780
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                6056
_reflns_number_total             6463
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc00196d2.cif
_cod_data_source_block           hnt01nmr01_0m
_cod_database_code               1550596
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.775
_shelx_estimated_absorpt_t_min   0.597
_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. Others
 Sof(C19)=Sof(C15)=Sof(H15)=Sof(C14)=Sof(C11)=Sof(C20)=Sof(H20)=Sof(C18)=
 Sof(H18)=Sof(C12)=Sof(H12)=Sof(C16)=Sof(C13)=Sof(H13)=Sof(C17)=Sof(H17)=1-
 FVAR(1)
 Sof(C8AA)=Sof(H8AA)=Sof(C0AA)=Sof(H0AA)=Sof(C2AA)=Sof(H2AA)=Sof(C9AA)=
 Sof(H9AA)=Sof(C1AA)=Sof(C3AA)=Sof(C6AA)=Sof(H6AA)=Sof(C5AA)=Sof(H5AA)=
 Sof(C4AA)=Sof(C7AA)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C9(H9), C7(H7), C1(H1A), C15(H15), C6(H6), C20(H20), C18(H18),
  C12(H12), C13(H13), C17(H17), C8AA(H8AA), C0AA(H0AA), C2AA(H2AA), C9AA(H9AA),
 C6AA(H6AA), C5AA(H5AA)
3.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_olex2_submission_special_instructions 'No special instructions were received'