A multicomponent reaction for modular assembly of indole-fused heterocycles
Li, Jiaming; Ni, Hao; Zhang, Weiwei; Lai, Zhencheng; Jin, Huimin; Zeng, Linwei; Cui, Sunliang; Chemical Science 15 (2024) 5211–5217; doi:10.1039/D4SC00522H

data_1571148
_publ_section_title
;
 A multicomponent reaction for modular assembly of indole-fused
 heterocycles
;
_journal_issue                   14
_journal_name_full               'Chemical Science'
_journal_page_first              5211
_journal_page_last               5217
_journal_paper_doi               10.1039/D4SC00522H
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C14 H17 Cl N2 S'
_chemical_formula_sum            'C14 H17 Cl N2 S'
_chemical_formula_weight         280.80
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-03-12
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-03-17 deposited with the CCDC.	2024-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                80.365(3)
_cell_angle_beta                 89.851(3)
_cell_angle_gamma                84.042(3)
_cell_formula_units_Z            2
_cell_length_a                   5.0074(4)
_cell_length_b                   9.0205(7)
_cell_length_c                   15.1568(13)
_cell_measurement_reflns_used    5035
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      60.576
_cell_measurement_theta_min      2.573
_cell_volume                     671.24(9)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11083
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.576
_diffrn_reflns_theta_min         2.573
_diffrn_source_current           3.57
_diffrn_source_power             0.24957869999999996
_diffrn_source_voltage           69.91
_exptl_absorpt_coefficient_mu    2.528
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0676 before and 0.0576 after correction.
The Ratio of minimum to maximum transmission is 0.8985.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3025
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.140
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0491
_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^)+(0.0634P)^2^+0.2526P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1273
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2657
_reflns_number_total             3025
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc00522h2.cif
_cod_data_source_block           230307_ljm_8_3_3_0m
_cod_depositor_comments
'Adding full bibliography for 1571147--1571150.cif.'
_cod_database_code               1571148
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.928
_shelx_estimated_absorpt_t_min   0.632
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_shelx_res_checksum              44990
_olex2_submission_special_instructions 'No special instructions were received'