Palladium-catalyzed oxidative cycloaddition of 1-indanones and internal aryl alkynes toward benzo[<i>c</i>]fluorenone derivatives.
Zhang, Xu; Ni, Tongtong; Chang, Mengfan; Li, Wenguang; Xu, Xuefeng; Chemical communications (Cambridge, England) 61 (2025) 5186–5189; doi:10.1039/d4cc06591c

data_7134306
_publ_section_title
;
 Palladium-catalyzed oxidative cycloaddition of 1-indanones and internal
 aryl alkynes toward benzo[<i>c</i>]fluorenone derivatives.
;
_journal_issue                   27
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5186
_journal_page_last               5189
_journal_paper_doi               10.1039/d4cc06591c
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C24 H13 F3 O'
_chemical_formula_sum            'C24 H13 F3 O'
_chemical_formula_weight         374.34
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-12-05
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-12-16 deposited with the CCDC.	2025-03-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.865(2)
_cell_length_b                   12.8982(19)
_cell_length_c                   9.3217(14)
_cell_measurement_reflns_used    2337
_cell_measurement_temperature    296.15
_cell_volume                     1787.3(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0682
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10346
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.605
_diffrn_reflns_theta_min         2.090
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0561 before and 0.0353 after correction.
The Ratio of minimum to maximum transmission is 0.9062.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             768
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 828 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4020
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1106
_refine_ls_R_factor_gt           0.0520
_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^)+(0.0570P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1233
_reflns_Friedel_coverage         0.825
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.936
_reflns_number_gt                2442
_reflns_number_total             4020
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc06591c2.cif
_cod_data_source_block           5
_cod_depositor_comments          'Adding full bibliography for 7134306.cif.'
_cod_original_cell_volume        1787.3(5)
_cod_database_code               7134306
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C00E(H00E), C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J),
 C00L(H00L), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R),
 C00S(H00S)
;
_olex2_submission_special_instructions 'No special instructions were received'