Ruthenium(ii)-catalyzed synthesis of indazolone-fused cinnolines via C-H coupling with diazo compounds.
Su, Lin; Yu, Zheng; Ren, Peiling; Luo, Zhi; Hou, Wei; Xu, Hongtao; Organic & biomolecular chemistry 16 (2018) 7236–7244; doi:10.1039/c8ob02071j

data_7156427
_publ_section_title
;
 Ruthenium(ii)-catalyzed synthesis of indazolone-fused cinnolines via C-H
 coupling with diazo compounds.
;
_journal_issue                   39
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7236
_journal_page_last               7244
_journal_paper_doi               10.1039/c8ob02071j
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C24 H17 Br N2 O3'
_chemical_formula_sum            'C24 H17 Br N2 O3'
_chemical_formula_weight         461.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc1zpkjr
_audit_creation_date             2018-04-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_audit_update_record
;
2018-05-05 deposited with the CCDC.
2018-09-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.717(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.811(3)
_cell_length_b                   20.892(8)
_cell_length_c                   10.950(4)
_cell_measurement_reflns_used    2513
_cell_measurement_temperature    173
_cell_measurement_theta_max      23.668
_cell_measurement_theta_min      2.401
_cell_volume                     1940.3(12)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      173
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.982
_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  0.0623
_diffrn_reflns_av_unetI/netI     0.0806
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12115
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.496
_diffrn_reflns_theta_min         2.164
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.149
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.3894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1238 before and 0.0618 after correction. The Ratio of minimum to maximum transmission is 0.5224. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.708
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       0.0040(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3940
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0541P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1245
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3009
_reflns_number_total             3940
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02071j2.cif
_cod_data_source_block           mo_20180288-xht_0m
_cod_depositor_comments          'Adding full bibliography for 7156427.cif.'
_cod_database_code               7156427
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.783
_shelx_estimated_absorpt_t_min   0.584
_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. Uiso/Uaniso restraints and constraints
Uanis(C24) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(O2) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C12(H12), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21)
3.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_olex2_submission_special_instructions 'No special instructions were received'