Substrate-directed divergent synthesis of fused indole polycycles through Rh(II)-catalyzed cascade reactions of bis(diazo)indolin-2-ones
Zhao, Yang; Niu, Xin-Yue; Yang, Hong; Yang, Jing; Wang, Zhizeng; Wang, Qi-Lin; Chemical Communications  (2022) –; doi:10.1039/D2CC02686D

data_7130316
_publ_section_title
;
 Substrate-directed divergent synthesis of fused indole polycycles through
 Rh(II)-catalyzed cascade reactions of bis(diazo)indolin-2-ones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02686D
_journal_year                    2022
_chemical_formula_moiety         'C23 H20 N2 O'
_chemical_formula_sum            'C23 H20 N2 O'
_chemical_formula_weight         340.41
_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     direct
_audit_creation_date             2020-06-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-04-22 deposited with the CCDC.	2022-07-04 downloaded from the CCDC.
;
_cell_angle_alpha                87.411(11)
_cell_angle_beta                 65.196(11)
_cell_angle_gamma                76.494(12)
_cell_formula_units_Z            2
_cell_length_a                   9.674(3)
_cell_length_b                   9.935(3)
_cell_length_c                   10.704(3)
_cell_measurement_reflns_used    3936
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.51
_cell_measurement_theta_min      2.79
_cell_volume                     906.4(5)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      273.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_av_unetI/netI     0.0771
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11940
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.358
_diffrn_reflns_theta_min         2.387
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1426 before and 0.0904 after correction. The Ratio of minimum to maximum transmission is 0.6980. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_description       prism
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3682
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.1068
_refine_ls_R_factor_gt           0.0814
_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^)+(0.1541P)^2^+0.1537P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2359
_refine_ls_wR_factor_ref         0.2680
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2493
_reflns_number_total             3682
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02686d2.cif
_cod_data_source_block           a
_cod_original_cell_volume        906.5(5)
_cod_database_code               7130316
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.980
_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, All O(H) groups
2. Restrained distances
 C23A-O1A
 1.45 with sigma of 0.02
 C23-O1
 1.65 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C22) = Uanis(C22A)
Uanis(C23) = Uanis(C23A)
Uanis(O1) = Uanis(O1A)
4. Others
 Sof(C22A)=Sof(H22C)=Sof(H22D)=Sof(C23A)=Sof(H23C)=Sof(H23D)=Sof(O1A)=
 Sof(H1AA)=1-FVAR(1)
 Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(O1)=Sof(H1A)=
 FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C23(H23A,H23B), C22A(H22C,H22D), C23A(H23C,H23D)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14),
 C16(H16), C17(H17), C19(H19), C20(H20)
5.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
5.d Idealised tetrahedral OH refined as rotating group:
 O1(H1A), O1A(H1AA)
;
_shelx_res_checksum              7509
_shelx_hkl_checksum              50382
_olex2_submission_special_instructions 'No special instructions were received'