A radical-mediated multicomponent cascade reaction for the synthesis of azide-biindole derivatives.
Liu, Xiaoyu; He, Kun; Gao, Na; Jiang, Peiyun; Lin, Jun; Jin, Yi; Chemical communications (Cambridge, England) 57 (2021) 9696–9699; doi:10.1039/d1cc03853b

data_7128896
_publ_section_title
;
 A radical-mediated multicomponent cascade reaction for the synthesis of
 azide-biindole derivatives.
;
_journal_issue                   76
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9696
_journal_page_last               9699
_journal_paper_doi               10.1039/d1cc03853b
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C22 H19 N7'
_chemical_formula_sum            'C22 H19 N7'
_chemical_formula_weight         381.44
_chemical_melting_point          417
_chemical_name_systematic
3'-azido-7,7'-dimethyl-2'-(4-methyl-1H-imidazol-1-yl)-1H,3'H-3,3'-biindole
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-08-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-08-24 deposited with the CCDC.	2021-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                68.608(5)
_cell_angle_beta                 84.564(5)
_cell_angle_gamma                75.181(4)
_cell_formula_units_Z            2
_cell_length_a                   8.0191(10)
_cell_length_b                   10.4708(13)
_cell_length_c                   13.0070(16)
_cell_measurement_reflns_used    4225
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.75
_cell_measurement_theta_min      2.63
_cell_volume                     983.1(2)
_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 (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      170.0
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14068
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.147
_diffrn_reflns_theta_min         2.213
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0994 before and 0.0525 after correction.
The Ratio of minimum to maximum transmission is 0.9030.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane/Hexyl hydride'
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4139
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0514
_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^)+(0.0617P)^2^+0.2241P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1445
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2681
_reflns_number_total             4139
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc03853b2.cif
_cod_data_source_block           mo_210824_09066_0m
_cod_depositor_comments
'Adding full bibliography for 7128895--7128897.cif.'
_cod_database_code               7128896
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.994
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N7-H7
 0.88 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C10(H10), C12(H12), C15(H15), C18(H18), C19(H19),
 C20(H20)
3.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C13(H13A,H13B,H13C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              30826
_olex2_submission_special_instructions 'No special instructions were received'