Asymmetric construction of polycyclic indole derivatives with different ring connectivities by an organocatalysis triggered two-step sequence
Xie, Chao-Chao; Tan, Rui; Liu, Yan-Kai; Organic Chemistry Frontiers 6 (2019) 919–; doi:10.1039/C8QO01406J

data_1554584
_publ_section_title
;
 Asymmetric construction of polycyclic indole derivatives with different
 ring connectivities by an organocatalysis triggered two-step sequence
;
_journal_issue                   7
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              919
_journal_paper_doi               10.1039/C8QO01406J
_journal_volume                  6
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H20 Br N3 O4'
_chemical_formula_sum            'C22 H20 Br N3 O4'
_chemical_formula_weight         470.31
_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     direct
_audit_creation_date             2018-06-04
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_audit_update_record
;
2018-11-08 deposited with the CCDC.
2019-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.724(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.2282(14)
_cell_length_b                   9.1743(14)
_cell_length_c                   12.829(2)
_cell_measurement_reflns_used    2544
_cell_measurement_temperature    120.15
_cell_measurement_theta_max      23.361
_cell_measurement_theta_min      2.381
_cell_volume                     1022.4(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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_temperature      120.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0782
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6118
_diffrn_reflns_point_group_measured_fraction_full 0.936
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         2.788
_exptl_absorpt_coefficient_mu    2.045
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.0824 before and 0.0595 after correction. The Ratio of minimum to maximum transmission is 0.7644. The \l/2 correction factor is 0.00150.'
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 1115 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.019(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.839
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4202
_refine_ls_number_restraints     58
_refine_ls_restrained_S_all      0.843
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0326
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[\s^2^(Fo^2^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0660
_refine_ls_wR_factor_ref         0.0730
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    0.865
_reflns_Friedel_fraction_max     0.812
_reflns_number_gt                3248
_reflns_number_total             4202
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo01406j2.cif
_cod_data_source_block           180603xcc1_0m
_cod_database_code               1554584
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O3A) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(O4A) \\sim Ueq, Uanis(O4)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Rigid body (RIGU) restrains
 O3, O4, N3, O3A, O4A, C17
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: O3(0.5) O4(0.5) O3A(0.5) O4A(0.5)
5.a Ternary CH refined with riding coordinates:
 C4(H4), C15(H15), C16(H16)
5.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C13(H13A,H13B), C14(H14A,H14B), C17(H17A,H17B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C19(H19), C21(H21),
 C22(H22)
;
_shelx_res_checksum              95988
_shelx_hkl_checksum              34541
_olex2_submission_special_instructions 'No special instructions were received'