Rapid access to 9-arylfluorene and spirobifluorene through Pd-catalysed C–H arylation/deaminative annulation
Wu, Yu; Wu, Feng-Wei; Zhou, Kun; Li, Yiming; Chen, Lei; Wang, Shuang; Xu, Zhen-Yuan; Lou, Shao-Jie; Xu, Dan-Qian; Chemical Communications  (2022) –; doi:10.1039/D2CC01355J

data_7130053
_publ_section_title
;
 Rapid access to 9-arylfluorene and spirobifluorene through Pd-catalysed
 C--H arylation/deaminative annulation
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01355J
_journal_year                    2022
_chemical_formula_moiety         'C19 H13 Cl'
_chemical_formula_sum            'C19 H13 Cl'
_chemical_formula_weight         276.74
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-28
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_audit_update_record
;
2022-02-23 deposited with the CCDC.	2022-04-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.943(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0500(9)
_cell_length_b                   6.2114(6)
_cell_length_c                   24.788(2)
_cell_measurement_reflns_used    3954
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      54.87
_cell_measurement_theta_min      4.38
_cell_volume                     1383.2(2)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'Bruker BIS V6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      193.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Metaljet PHOTON II'
_diffrn_measurement_method       '\w and \f shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_av_unetI/netI     0.0720
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            9267
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.206
_diffrn_reflns_theta_min         4.377
_diffrn_source                   MetalJet
_diffrn_source_current           2.86
_diffrn_source_power             0.19937059999999998
_diffrn_source_type              'Liquid Metal source'
_diffrn_source_voltage           69.71
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.520
_exptl_absorpt_correction_T_max  0.7366
_exptl_absorpt_correction_T_min  0.6544
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1150 before and 0.0907 after correction.
The Ratio of minimum to maximum transmission is 0.8884.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         2973
_refine_ls_number_restraints     336
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1076
_refine_ls_R_factor_gt           0.0598
_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^)+(0.0580P)^2^+0.7355P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1459
_refine_ls_wR_factor_ref         0.1658
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1833
_reflns_number_total             2973
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc01355j2.cif
_cod_data_source_block           a_CCDC1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7130053
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.863
_shelx_estimated_absorpt_t_min   0.839
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
C4A \\sim C5A \\sim C6A \\sim C1A \\sim C2A \\sim C3A: within 2A with sigma of
0.02 and sigma for terminal atoms of 0.04 within 2A
Uanis(C5A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
4. Others
 Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(C5A)=Sof(C4A)=Sof(H4A)=Sof(C3A)=Sof(H3A)=
 Sof(C2A)=Sof(H2A)=Sof(C1A)=Sof(C6A)=Sof(C9A)=Sof(C13A)=Sof(H13A)=Sof(C10A)=
 Sof(H10A)=Sof(C12A)=Sof(H12A)=Sof(C11A)=Sof(H11A)=Sof(Cl1A)=1-FVAR(1)
 Sof(Cl1)=Sof(C7)=Sof(H7)=Sof(C6)=Sof(C8)=Sof(C5)=Sof(C9)=Sof(C4)=Sof(H4)=
 Sof(C13)=Sof(H13)=Sof(C10)=Sof(H10)=Sof(C1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=
 Sof(C12)=Sof(H12)=Sof(C11)=Sof(H11)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C7(H7), C7A(H7A)
5.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C19(H19), C4(H4), C16(H16), C17(H17), C13(H13), C10(H10), C18(H18),
 C2(H2), C3(H3), C12(H12), C11(H11), C4A(H4A), C3A(H3A), C2A(H2A), C13A(H13A),
 C10A(H10A), C12A(H12A), C11A(H11A)
5.c Fitted hexagon refined as free rotating group:
 C5A(C4A,C3A,C2A,C1A,C6A)
;
_shelx_res_checksum              81659
_shelx_hkl_checksum              58599
_olex2_submission_special_instructions 'No special instructions were received'