General Approach To Construct Azepino[2,3-<i>b</i>:4,5-<i>b</i>']diindoles, Azocino[2,3-<i>b</i>:4,5-<i>b</i>']diindoles, and Azonino[2,3-<i>b</i>:4,5-<i>b</i>']diindoles via Rh(II)-Catalyzed Reactions of 3-Diazoindolin-2-imines with 3-(Bromoalkyl)indoles.
Sheng, Guorong; Li, Zhenmin; Mao, Jianming; Lu, Ping; Wang, Yanguang; The Journal of organic chemistry 84 (2019) 9561–9569; doi:10.1021/acs.joc.9b01169

data_4034390
_publ_section_title
;
 General Approach To Construct
 Azepino[2,3-<i>b</i>:4,5-<i>b</i>']diindoles,
 Azocino[2,3-<i>b</i>:4,5-<i>b</i>']diindoles, and
 Azonino[2,3-<i>b</i>:4,5-<i>b</i>']diindoles via Rh(II)-Catalyzed
 Reactions of 3-Diazoindolin-2-imines with 3-(Bromoalkyl)indoles.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9561
_journal_page_last               9569
_journal_paper_doi               10.1021/acs.joc.9b01169
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C35 H33 N3 O2 S'
_chemical_formula_sum            'C35 H33 N3 O2 S'
_chemical_formula_weight         559.70
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-12-17
_audit_creation_method
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Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
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_cell_angle_alpha                90
_cell_angle_beta                 96.549(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9128(9)
_cell_length_b                   9.6989(5)
_cell_length_c                   19.5579(10)
_cell_measurement_reflns_used    3134
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4115
_cell_measurement_theta_min      3.2794
_cell_volume                     2810.4(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -41.00   40.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.5304   86.0000  -29.0000 81

  2 omega  -89.00   20.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.5304  -77.0000 -150.0000 109
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0406721000
_diffrn_orient_matrix_UB_12      -0.0376754000
_diffrn_orient_matrix_UB_13      0.0006099000
_diffrn_orient_matrix_UB_21      0.0056007000
_diffrn_orient_matrix_UB_22      -0.0289482000
_diffrn_orient_matrix_UB_23      -0.0325584000
_diffrn_orient_matrix_UB_31      0.0246448000
_diffrn_orient_matrix_UB_32      -0.0555594000
_diffrn_orient_matrix_UB_33      0.0165149000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11729
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         3.286
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44743
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         5137
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0640
_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^)+(0.1117P)^2^+0.1727P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1655
_refine_ls_wR_factor_ref         0.1878
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3696
_reflns_number_total             5137
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01169_si_004.cif
_cod_data_source_block           171216_sgr5_055b
_cod_database_code               4034390
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H N O S'
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.943
_reflns_odcompleteness_completeness 99.56
_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 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), C12(H12A,H12B), C29(H29A,H29B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C17(H17), C18(H18), C19(H19), C20(H20),
 C23(H23), C24(H24), C26(H26), C27(H27), C31(H31), C32(H32), C33(H33), C34(H34),
  C35(H35)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C28(H28A,H28B,H28C)
;
_shelx_res_checksum              74921
_shelx_hkl_checksum              61415
_olex2_submission_special_instructions 'No special instructions were received'