Rh(III)-catalyzed [4 + 1] annulation of 1-arylindazolones with alkynyl cyclobutanols: access to indazolo[1,2-<i>a</i>]indazolones.
Hu, Jiang; Liu, Jidan; Cui, Wenwen; Zheng, Liyao; Wang, Renjie; Liu, Zhao-Qing; Pu, Shouzhi; Organic & biomolecular chemistry 22 (2024) 6500–6505; doi:10.1039/d4ob01067a

data_7160132
_publ_section_title
;
 Rh(III)-catalyzed [4 + 1] annulation of 1-arylindazolones with alkynyl
 cyclobutanols: access to indazolo[1,2-<i>a</i>]indazolones.
;
_journal_issue                   32
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6500
_journal_page_last               6505
_journal_paper_doi               10.1039/d4ob01067a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C25 H21 Cl N2 O2'
_chemical_formula_sum            'C25 H21 Cl N2 O2'
_chemical_formula_weight         415.88
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-11-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-02-01 deposited with the CCDC.	2024-07-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.017(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.944(3)
_cell_length_b                   19.542(7)
_cell_length_c                   12.592(4)
_cell_measurement_reflns_used    2309
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.328
_cell_measurement_theta_min      2.537
_cell_volume                     2167.3(13)
_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      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0979
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12769
_diffrn_reflns_point_group_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.522
_diffrn_reflns_theta_min         2.084
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5947
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1207 before and 0.0550 after correction.
The Ratio of minimum to maximum transmission is 0.7976.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_F_000             868
_refine_diff_density_max         1.637
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.157
_refine_ls_abs_structure_details
;
 Flack x determined using 1547 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.20(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.959
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     544
_refine_ls_number_reflns         8706
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.959
_refine_ls_R_factor_all          0.2093
_refine_ls_R_factor_gt           0.1500
_refine_ls_shift/su_max          0.414
_refine_ls_shift/su_mean         0.048
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3590
_refine_ls_wR_factor_ref         0.3784
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_full    0.881
_reflns_Friedel_fraction_max     0.783
_reflns_number_gt                4969
_reflns_number_total             8706
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01067a2.cif
_cod_data_source_block           2
_cod_depositor_comments
;

2025-04-01
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C100 H80 Cl4 N8 O8'
_cod_original_formula_weight         1663.52
_cod_original_formula_moiety         '4(C25 H21 Cl N2 O2)'
_cod_original_formula_units_Z            1
_cod_original_cell_volume        2167.4(13)
_cod_database_code               7160132
_shelx_shelxl_version_number     2016/6
_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.a Secondary CH2 refined with riding coordinates:
 C00H(H00F,H00G), C00K(H00A,H00B), C00R(H00C,H00D), C01B(H01I,H01J), C12(H12A,
 H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C00B(H00E), C00J(H00J), C00Q(H00Q), C00T(H00T), C00U(H00U), C00V(H00V),
 C00Y(H00Y), C00Z(H00Z), C011(H011), C012(H012), C015(H015), C016(H016),
 C017(H017), C019(H019), C01A(H01F), C01C(H01K), C01D(H01D), C01E(H01E),
 C01F(H01L), C01G(H01G), C01H(H01H), C01I(H01M), C01J(H01P), C01N(H01N),
 C01O(H01O)
2.c Idealised Me refined as rotating group:
 C01K(H01Q,H01R,H01S), C01L(H01A,H01B,H01C)
2.d Idealised tetrahedral OH refined as rotating group:
 O005(H005)
;
_shelx_res_checksum              2468
_olex2_submission_special_instructions 'No special instructions were received'