Synthesis of polyfluoroarene-substituted benzofuran derivatives via cooperative Pd/Cu catalysis.
Shen, Yi; Wu, Xin-Xing; Chen, Si; Xia, Yu; Liang, Yong-Min; Chemical communications (Cambridge, England) 54 (2018) 2256–2259; doi:10.1039/c8cc00489g

data_7121244
_publ_section_title
;
 Synthesis of polyfluoroarene-substituted benzofuran derivatives via
 cooperative Pd/Cu catalysis.
;
_journal_issue                   18
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2256
_journal_page_last               2259
_journal_paper_doi               10.1039/c8cc00489g
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C15 H9 F5 O2'
_chemical_formula_sum            'C15 H9 F5 O2'
_chemical_formula_weight         316.22
_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     iterative
_audit_creation_date             2017-05-12
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Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
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_audit_update_record
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2017-12-26 deposited with the CCDC.
2018-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.114(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.7847(11)
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_cell_length_c                   28.524(4)
_cell_measurement_reflns_used    1151
_cell_measurement_temperature    296.61(19)
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_cell_measurement_theta_min      3.8250
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_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
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_diffrn_ambient_temperature      296.61(19)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega    8.00   79.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000 -180.0000 71

  2 omega    8.00   65.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000    0.0000 57

  3 omega  -10.00   95.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000  -90.0000 105
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
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_diffrn_orient_matrix_UB_13      0.0215089000
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_diffrn_orient_matrix_UB_22      0.0048074000
_diffrn_orient_matrix_UB_23      0.0072337000
_diffrn_orient_matrix_UB_31      0.0003630000
_diffrn_orient_matrix_UB_32      0.0731505000
_diffrn_orient_matrix_UB_33      -0.0109394000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_av_unetI/netI     0.1210
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            9992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.480
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         5195
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1804
_refine_ls_R_factor_gt           0.0790
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0671P)^2^+0.9360P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1733
_refine_ls_wR_factor_ref         0.2310
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2172
_reflns_number_total             5195
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc00489g2.cif
_cod_data_source_block           shengyi_0508
_cod_depositor_comments
'Adding full bibliography for 7121244--7121245.cif.'
_cod_database_code               7121244
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H O N'
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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), C14(H14A,H14B), C27(H27A,H27B), C28(H28A,H28B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C30(H30A,H30B,H30C)
;
_olex2_date_sample_data_collection 2017-05-09
_olex2_submission_special_instructions 'No special instructions were received'