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_4034391
_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.
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_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         'C27 H25 N3 O2 S'
_chemical_formula_sum            'C27 H25 N3 O2 S'
_chemical_formula_weight         455.56
_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             2017-09-26
_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                66.676(10)
_cell_angle_beta                 66.523(10)
_cell_angle_gamma                89.163(7)
_cell_formula_units_Z            2
_cell_length_a                   10.2015(9)
_cell_length_b                   10.5115(10)
_cell_length_c                   12.4818(14)
_cell_measurement_reflns_used    2044
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3618
_cell_measurement_theta_min      3.3214
_cell_volume                     1110.9(2)
_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)
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_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      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -47.00   40.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6246   86.0000  -63.0000 87

  2 omega  -86.00   13.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6246  -77.0000   60.0000 99

  3 omega  -48.00   40.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6246   86.0000 -178.0000 88
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0751951000
_diffrn_orient_matrix_UB_12      0.0278370000
_diffrn_orient_matrix_UB_13      -0.0329315000
_diffrn_orient_matrix_UB_21      -0.0049180000
_diffrn_orient_matrix_UB_22      0.0160509000
_diffrn_orient_matrix_UB_23      0.0514406000
_diffrn_orient_matrix_UB_31      0.0154485000
_diffrn_orient_matrix_UB_32      -0.0672889000
_diffrn_orient_matrix_UB_33      0.0309160000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6860
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         3.328
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87290
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4049
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0579
_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^)+(0.0896P)^2^+0.2473P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1503
_refine_ls_wR_factor_ref         0.1719
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3076
_reflns_number_total             4049
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01169_si_002.cif
_cod_data_source_block           170926_sgr5_020b
_cod_database_code               4034391
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c h n o s'
_shelx_estimated_absorpt_t_max   0.952
_shelx_estimated_absorpt_t_min   0.918
_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:
 C17(H17A,H17B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C26(H26), C22(H22), C25(H25), C1(H1), C4(H4), C23(H23), C13(H13),
 C14(H14), C3(H3), C12(H12), C2(H2)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              11502
_shelx_hkl_checksum              6791
_olex2_submission_special_instructions 'No special instructions were received'