Palladium-catalyzed allylic alkylation dearomatization of β-naphthols and indoles with <i>gem</i>-difluorinated cyclopropanes.
Fu, Zhiyuan; Zhu, Jianping; Guo, Songjin; Lin, Aijun; Chemical communications (Cambridge, England) 57 (2021) 1262–1265; doi:10.1039/d0cc07529a

data_7127675
_publ_section_title
;
 Palladium-catalyzed allylic alkylation dearomatization of \b-naphthols
 and indoles with <i>gem</i>-difluorinated cyclopropanes.
;
_journal_issue                   10
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1262
_journal_page_last               1265
_journal_paper_doi               10.1039/d0cc07529a
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C23 H20 F N'
_chemical_formula_sum            'C23 H20 F N'
_chemical_formula_weight         329.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-31 deposited with the CCDC.	2020-12-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.876(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.0769(10)
_cell_length_b                   6.4038(2)
_cell_length_c                   24.0305(10)
_cell_measurement_reflns_used    2840
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.225
_cell_measurement_theta_min      2.295
_cell_volume                     3517.7(2)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'D8 VENTURE '
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            12779
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.424
_diffrn_reflns_theta_min         2.295
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1413 before and 0.0517 after correction. The Ratio of minimum to maximum transmission is 0.9174. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3570
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0503
_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^)+(0.0433P)^2^+2.2622P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1235
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2367
_reflns_number_total             3570
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc07529a2.cif
_cod_data_source_block           220191199fzy_0m
_cod_depositor_comments
'Adding full bibliography for 7127675--7127676.cif.'
_cod_database_code               7127675
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.985
_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.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C9(H9), C11(H11), C7(H7), C2(H2), C19(H19), C22(H22), C21(H21),
 C4(H4), C20(H20), C6(H6), C5(H5)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C16(H16A,H16B,H16C)
;
_olex2_submission_special_instructions 'No special instructions were received'