#------------------------------------------------------------------------------
#$Date: 2022-02-10 00:55:46 +0200 (Thu, 10 Feb 2022) $
#$Revision: 272887 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/96/7129693.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7129693
loop_
_publ_author_name
'Ponce-de-León, Jaime'
'Marcos-Ayuso, Guillermo'
'Casares, Juan A.'
'Espinet, Pablo'
_publ_section_title
;
 Pd/Cu bimetallic catalysis to access highly fluorinated biaryls from aryl
 halides and fluorinated arenes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC00141A
_journal_year                    2022
_chemical_formula_moiety         'C12 H3 F7'
_chemical_formula_sum            'C12 H3 F7'
_chemical_formula_weight         280.14
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-12-28 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_cell_angle_alpha                75.019(9)
_cell_angle_beta                 79.707(9)
_cell_angle_gamma                78.279(10)
_cell_formula_units_Z            2
_cell_length_a                   7.3590(9)
_cell_length_b                   7.5748(9)
_cell_length_c                   9.8836(10)
_cell_measurement_reflns_used    943
_cell_measurement_temperature    294
_cell_measurement_theta_max      23.5220
_cell_measurement_theta_min      3.6280
_cell_volume                     516.46(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_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      294
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4757
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.837
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  14.00   1.00    2.13    --  -10.48 -99.00-150.00   26
  2  ω    -84.00  10.00   1.00    2.13    --  -10.48 -57.00 -60.00   94
  3  ω     -4.00  84.00   1.00    2.13    --   12.36  57.00-150.00   88
  4  ω    -64.00  35.00   1.00    2.13    --   12.36 -77.00  90.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0434517000
_diffrn_orient_matrix_UB_12      -0.0034847000
_diffrn_orient_matrix_UB_13      0.0705277000
_diffrn_orient_matrix_UB_21      -0.0757967000
_diffrn_orient_matrix_UB_22      0.0676517000
_diffrn_orient_matrix_UB_23      -0.0251548000
_diffrn_orient_matrix_UB_31      -0.0472468000
_diffrn_orient_matrix_UB_32      -0.0712086000
_diffrn_orient_matrix_UB_33      -0.0034862000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4325
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.448
_diffrn_reflns_theta_min         3.337
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.514
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.801
_exptl_crystal_description       plate
_exptl_crystal_F_000             276
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-pentane'
_exptl_crystal_size_max          0.539
_exptl_crystal_size_mid          0.491
_exptl_crystal_size_min          0.082
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2392
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.1160
_refine_ls_R_factor_gt           0.0504
_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/[σ²(Fo²)+(0.0531P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1472
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1181
_reflns_number_total             2392
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc00141a2.cif
_cod_data_source_block           3bn
_cod_database_code               7129693
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C12 H3 F7'
_chemical_oxdiff_usercomment     'colourless plate'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C10(H10), C11(H11)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.592
_oxdiff_exptl_absorpt_empirical_full_min 0.737
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F5 F 0.4190(2) -0.0361(2) 0.24391(16) 0.0708(5) Uani 1 1 d . . . . .
F6 F 0.0725(2) 0.2294(2) 0.23446(15) 0.0764(6) Uani 1 1 d . . . . .
F1 F 0.4761(2) 0.5618(2) 0.26889(17) 0.0745(5) Uani 1 1 d . . . . .
F7 F -0.2109(2) 0.2194(3) 0.44447(17) 0.0887(6) Uani 1 1 d . . . . .
F4 F 0.7089(3) -0.0313(2) 0.03668(19) 0.0885(6) Uani 1 1 d . . . . .
F2 F 0.7659(3) 0.5642(2) 0.06268(18) 0.0888(6) Uani 1 1 d . . . . .
F3 F 0.8832(3) 0.2693(3) -0.05623(17) 0.0930(6) Uani 1 1 d . . . . .
C6 C 0.4365(3) 0.2628(3) 0.2629(2) 0.0443(6) Uani 1 1 d . . . . .
C7 C 0.2798(4) 0.2592(3) 0.3807(2) 0.0456(6) Uani 1 1 d . . . . .
C5 C 0.5021(4) 0.1157(3) 0.1996(2) 0.0519(7) Uani 1 1 d . . . . .
C1 C 0.5311(4) 0.4127(3) 0.2132(2) 0.0499(6) Uani 1 1 d . . . . .
C8 C 0.1046(4) 0.2413(3) 0.3617(2) 0.0517(7) Uani 1 1 d . . . . .
C9 C -0.0413(4) 0.2366(4) 0.4699(3) 0.0592(7) Uani 1 1 d . . . . .
C4 C 0.6499(4) 0.1158(4) 0.0938(3) 0.0573(7) Uani 1 1 d . . . . .
C2 C 0.6801(4) 0.4157(4) 0.1070(3) 0.0576(7) Uani 1 1 d . . . . .
C12 C 0.3035(4) 0.2723(4) 0.5137(3) 0.0565(7) Uani 1 1 d . . . . .
H12 H 0.4205 0.2841 0.5302 0.068 Uiso 1 1 calc R . . . .
C3 C 0.7381(4) 0.2672(4) 0.0477(2) 0.0603(8) Uani 1 1 d . . . . .
C10 C -0.0175(4) 0.2484(4) 0.6004(3) 0.0628(8) Uani 1 1 d . . . . .
H10 H -0.1166 0.2433 0.6736 0.075 Uiso 1 1 calc R . . . .
C11 C 0.1561(4) 0.2681(4) 0.6219(3) 0.0638(8) Uani 1 1 d . . . . .
H11 H 0.1743 0.2787 0.7100 0.077 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 5 2 0.2455
-1 -5 -2 0.2455
5 0 1 0.3215
-5 0 -1 0.2155
5 -5 -1 0.2829
0 0 1 0.0279
0 0 -1 0.0539
-5 4 0 0.2601
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 C6 C7 122.5(2) . . ?
C5 C6 C1 115.7(2) . . ?
C1 C6 C7 121.8(2) . . ?
C8 C7 C6 120.7(2) . . ?
C8 C7 C12 117.3(2) . . ?
C12 C7 C6 121.9(2) . . ?
F5 C5 C6 119.1(2) . . ?
F5 C5 C4 118.1(2) . . ?
C4 C5 C6 122.8(2) . . ?
F1 C1 C6 119.5(2) . . ?
F1 C1 C2 118.0(2) . . ?
C2 C1 C6 122.4(3) . . ?
F6 C8 C7 120.1(2) . . ?
F6 C8 C9 118.6(2) . . ?
C9 C8 C7 121.4(2) . . ?
F7 C9 C8 118.6(2) . . ?
F7 C9 C10 120.2(2) . . ?
C10 C9 C8 121.2(3) . . ?
F4 C4 C5 120.4(2) . . ?
F4 C4 C3 120.2(2) . . ?
C3 C4 C5 119.4(3) . . ?
F2 C2 C1 120.0(3) . . ?
F2 C2 C3 120.7(2) . . ?
C3 C2 C1 119.4(2) . . ?
C7 C12 H12 119.5 . . ?
C11 C12 C7 121.0(3) . . ?
C11 C12 H12 119.5 . . ?
F3 C3 C4 120.0(3) . . ?
F3 C3 C2 119.7(3) . . ?
C2 C3 C4 120.3(2) . . ?
C9 C10 H10 120.7 . . ?
C9 C10 C11 118.6(3) . . ?
C11 C10 H10 120.7 . . ?
C12 C11 H11 119.8 . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H11 119.8 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F5 C5 1.349(3) . ?
F6 C8 1.349(3) . ?
F1 C1 1.341(3) . ?
F7 C9 1.354(3) . ?
F4 C4 1.338(3) . ?
F2 C2 1.339(3) . ?
F3 C3 1.342(3) . ?
C6 C7 1.484(3) . ?
C6 C5 1.378(3) . ?
C6 C1 1.388(3) . ?
C7 C8 1.374(3) . ?
C7 C12 1.387(3) . ?
C5 C4 1.368(4) . ?
C1 C2 1.375(4) . ?
C8 C9 1.372(4) . ?
C9 C10 1.359(4) . ?
C4 C3 1.367(4) . ?
C2 C3 1.359(4) . ?
C12 H12 0.9300 . ?
C12 C11 1.379(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.375(4) . ?
C11 H11 0.9300 . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0000 5.0000 2.0000 0.0802 0.2122 -0.4103
-1.0000 -5.0000 -2.0000 -0.0802 -0.2122 0.4103
5.0000 -0.0000 1.0000 -0.1467 -0.4041 -0.2397
-5.0000 0.0000 -1.0000 0.1467 0.4041 0.2397
5.0000 -5.0000 -1.0000 -0.2704 -0.6921 0.1233
-0.0000 0.0000 1.0000 0.0705 -0.0252 -0.0035
0.0000 -0.0000 -1.0000 -0.0705 0.0252 0.0035
-5.0000 4.0000 0.0000 0.2033 0.6496 -0.0486
