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#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/58/4125859.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_4125859
loop_
_publ_author_name
'Giffin, Kaitie A.'
'Pua, Lorraine A.'
'Piotrkowski, Sarah'
'Gabidullin, Bulat M.'
'Korobkov, Ilia'
'Hughes, Russell P.'
'Baker, R. Tom'
_publ_section_title
;
 Generation of Hydrofluoronickelacycles from Trifluoroethylene and Ni(0):
 Ligand Effects on Regio-/Stereoselectivity and Reactivity.
;
_journal_issue                   11
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4075
_journal_page_last               4086
_journal_paper_doi               10.1021/jacs.6b12607
_journal_volume                  139
_journal_year                    2017
_chemical_formula_sum            'C32 H28 F8 O6 P2 S2'
_chemical_formula_weight         786.60
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                99.725(4)
_cell_angle_beta                 98.579(4)
_cell_angle_gamma                107.584(3)
_cell_formula_units_Z            1
_cell_length_a                   8.0635(8)
_cell_length_b                   10.4307(10)
_cell_length_c                   11.0659(11)
_cell_measurement_reflns_used    3075
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.71
_cell_volume                     854.41(15)
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_collection       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8850
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.994
_diffrn_reflns_theta_min         1.911
_exptl_absorpt_coefficient_mu    0.337
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6771
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_description       block
_exptl_crystal_F_000             402
_exptl_crystal_size_max          0.232
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.848
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4067
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0654
_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)+(0.0715P)²+1.7054P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1721
_refine_ls_wR_factor_ref         0.1842
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3092
_reflns_number_total             4067
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja6b12607_si_007.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 4125858--4125859.cif.'
_cod_database_code               4125859
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.926
_shelx_estimated_absorpt_t_max   0.975
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
P1 P 0.19067(11) 0.26606(8) 0.37358(8) 0.0227(2) Uani 1 1 d . .
C1 C -0.0174(4) 0.1506(3) 0.2792(3) 0.0239(6) Uani 1 1 d . .
C2 C -0.0450(5) 0.1246(4) 0.1490(3) 0.0340(8) Uani 1 1 d . .
H2 H 0.0455 0.1706 0.1099 0.041 Uiso 1 1 calc R U
C3 C -0.2044(6) 0.0314(5) 0.0765(4) 0.0443(10) Uani 1 1 d . .
H3 H -0.2237 0.0124 -0.0124 0.053 Uiso 1 1 calc R U
C4 C -0.3353(6) -0.0338(4) 0.1348(4) 0.0453(10) Uani 1 1 d . .
H4 H -0.4448 -0.0977 0.0851 0.054 Uiso 1 1 calc R U
C5 C -0.3099(5) -0.0080(4) 0.2638(4) 0.0411(9) Uani 1 1 d . .
H5 H -0.4013 -0.0538 0.3023 0.049 Uiso 1 1 calc R U
C6 C -0.1504(5) 0.0851(4) 0.3372(4) 0.0326(8) Uani 1 1 d . .
H6 H -0.1320 0.1039 0.4261 0.039 Uiso 1 1 calc R U
C7 C 0.3460(4) 0.3297(3) 0.2799(3) 0.0250(7) Uani 1 1 d . .
C8 C 0.3649(5) 0.4570(4) 0.2509(4) 0.0376(8) Uani 1 1 d . .
H8 H 0.2945 0.5096 0.2788 0.045 Uiso 1 1 calc R U
C9 C 0.4884(6) 0.5060(5) 0.1805(4) 0.0496(11) Uani 1 1 d . .
H9 H 0.5045 0.5937 0.1612 0.060 Uiso 1 1 calc R U
C10 C 0.5872(6) 0.4290(5) 0.1387(4) 0.0476(11) Uani 1 1 d . .
H10 H 0.6686 0.4625 0.0882 0.057 Uiso 1 1 calc R U
C11 C 0.5706(5) 0.3034(4) 0.1687(4) 0.0414(9) Uani 1 1 d . .
H11 H 0.6428 0.2522 0.1412 0.050 Uiso 1 1 calc R U
C12 C 0.4492(5) 0.2525(4) 0.2387(4) 0.0336(8) Uani 1 1 d . .
H12 H 0.4357 0.1654 0.2588 0.040 Uiso 1 1 calc R U
C13 C 0.2841(5) 0.1903(4) 0.4869(3) 0.0310(7) Uani 1 1 d . .
H13A H 0.2030 0.1663 0.5436 0.047 Uiso 1 1 calc R U
H13B H 0.3989 0.2563 0.5353 0.047 Uiso 1 1 calc R U
H13C H 0.3016 0.1067 0.4440 0.047 Uiso 1 1 calc R U
C14 C 0.1557(4) 0.4142(4) 0.4604(3) 0.0279(7) Uani 1 1 d . .
C15 C 0.0054(5) 0.4402(3) 0.4598(3) 0.0276(7) Uani 1 1 d . .
H15 H -0.0999 0.3774 0.4040 0.033 Uiso 1 1 calc R U
C16 C 0.0732(6) 0.6804(5) 0.1425(4) 0.0493(11) Uani 1 1 d . .
F1 F 0.3086(3) 0.5031(3) 0.5330(3) 0.0556(7) Uani 1 1 d . .
F2 F 0.1946(5) 0.6840(4) 0.0724(3) 0.0943(12) Uani 1 1 d . .
F3 F -0.0629(4) 0.7031(3) 0.0789(3) 0.0704(9) Uani 1 1 d . .
F4 F 0.0136(4) 0.5539(3) 0.1625(3) 0.0780(10) Uani 1 1 d . .
S1 S 0.17347(13) 0.80699(10) 0.29028(9) 0.0374(3) Uani 1 1 d . .
O1 O 0.3035(5) 0.7592(4) 0.3495(4) 0.0677(10) Uani 1 1 d . .
O2 O 0.0255(5) 0.8000(4) 0.3495(3) 0.0691(10) Uani 1 1 d . .
O3 O 0.2410(5) 0.9327(3) 0.2498(3) 0.0587(9) Uani 1 1 d . .
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'
O O 0.0106 0.0060 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C13 P1 C1 112.19(16) . .
C13 P1 C7 110.74(16) . .
C1 P1 C7 111.75(16) . .
C13 P1 C14 106.34(17) . .
C1 P1 C14 109.00(15) . .
C7 P1 C14 106.48(16) . .
C2 C1 C6 120.4(3) . .
C2 C1 P1 120.2(3) . .
C6 C1 P1 119.4(3) . .
C3 C2 C1 119.8(4) . .
C3 C2 H2 120.1 . .
C1 C2 H2 120.1 . .
C4 C3 C2 119.4(4) . .
C4 C3 H3 120.3 . .
C2 C3 H3 120.3 . .
C5 C4 C3 121.3(4) . .
C5 C4 H4 119.4 . .
C3 C4 H4 119.4 . .
C4 C5 C6 119.8(4) . .
C4 C5 H5 120.1 . .
C6 C5 H5 120.1 . .
C5 C6 C1 119.3(3) . .
C5 C6 H6 120.3 . .
C1 C6 H6 120.3 . .
C8 C7 C12 120.6(3) . .
C8 C7 P1 119.5(3) . .
C12 C7 P1 119.9(3) . .
C9 C8 C7 118.8(4) . .
C9 C8 H8 120.6 . .
C7 C8 H8 120.6 . .
C10 C9 C8 120.4(4) . .
C10 C9 H9 119.8 . .
C8 C9 H9 119.8 . .
C9 C10 C11 121.0(4) . .
C9 C10 H10 119.5 . .
C11 C10 H10 119.5 . .
C12 C11 C10 119.7(4) . .
C12 C11 H11 120.1 . .
C10 C11 H11 120.1 . .
C11 C12 C7 119.5(4) . .
C11 C12 H12 120.3 . .
C7 C12 H12 120.3 . .
P1 C13 H13A 109.5 . .
P1 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
P1 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C15 C14 F1 120.7(3) . .
C15 C14 P1 128.4(3) . .
F1 C14 P1 110.9(2) . .
C14 C15 C15 122.6(4) . 2_566
C14 C15 H15 118.7 . .
C15 C15 H15 118.7 2_566 .
F3 C16 F4 107.4(4) . .
F3 C16 F2 108.8(4) . .
F4 C16 F2 108.4(4) . .
F3 C16 S1 112.1(3) . .
F4 C16 S1 110.6(3) . .
F2 C16 S1 109.5(3) . .
O1 S1 O3 115.6(2) . .
O1 S1 O2 115.2(3) . .
O3 S1 O2 114.0(2) . .
O1 S1 C16 104.0(2) . .
O3 S1 C16 102.4(2) . .
O2 S1 C16 103.1(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 C13 1.782(4) .
P1 C1 1.785(3) .
P1 C7 1.789(3) .
P1 C14 1.798(3) .
C1 C2 1.391(5) .
C1 C6 1.393(5) .
C2 C3 1.384(5) .
C2 H2 0.9500 .
C3 C4 1.382(6) .
C3 H3 0.9500 .
C4 C5 1.379(6) .
C4 H4 0.9500 .
C5 C6 1.387(5) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 C8 1.388(5) .
C7 C12 1.393(5) .
C8 C9 1.385(6) .
C8 H8 0.9500 .
C9 C10 1.365(6) .
C9 H9 0.9500 .
C10 C11 1.378(6) .
C10 H10 0.9500 .
C11 C12 1.375(5) .
C11 H11 0.9500 .
C12 H12 0.9500 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 C15 1.319(5) .
C14 F1 1.337(4) .
C15 C15 1.439(6) 2_566
C15 H15 0.9500 .
C16 F3 1.319(5) .
C16 F4 1.330(5) .
C16 F2 1.332(6) .
C16 S1 1.817(5) .
S1 O1 1.414(3) .
S1 O3 1.434(3) .
S1 O2 1.434(3) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6 O2 0.95 2.43 3.360(5) 166.1 2_566
C8 H8 F4 0.95 2.64 3.353(5) 132.3 .
C8 H8 O1 0.95 2.56 3.363(5) 141.9 .
C12 H12 O3 0.95 2.44 3.283(5) 148.3 1_545
C13 H13A O2 0.98 2.41 3.310(5) 152.1 2_566
C13 H13B O1 0.98 2.61 3.382(5) 136.0 2_666
C13 H13C O3 0.98 2.45 3.317(5) 147.9 1_545
C6 H6 O2 0.95 2.43 3.360(5) 166.1 2_566
C8 H8 F4 0.95 2.64 3.353(5) 132.3 .
C8 H8 O1 0.95 2.56 3.363(5) 141.9 .
C12 H12 O3 0.95 2.44 3.283(5) 148.3 1_545
C13 H13A O2 0.98 2.41 3.310(5) 152.1 2_566
C13 H13B O1 0.98 2.61 3.382(5) 136.0 2_666
C13 H13C O3 0.98 2.45 3.317(5) 147.9 1_545
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_4
C13 P1 C1 C2 -127.6(3) .
C7 P1 C1 C2 -2.5(3) .
C14 P1 C1 C2 114.9(3) .
C13 P1 C1 C6 51.2(3) .
C7 P1 C1 C6 176.2(3) .
C14 P1 C1 C6 -66.3(3) .
C6 C1 C2 C3 -1.0(5) .
P1 C1 C2 C3 177.8(3) .
C1 C2 C3 C4 0.6(6) .
C2 C3 C4 C5 -0.1(7) .
C3 C4 C5 C6 0.0(7) .
C4 C5 C6 C1 -0.4(6) .
C2 C1 C6 C5 0.8(5) .
P1 C1 C6 C5 -177.9(3) .
C13 P1 C7 C8 -137.6(3) .
C1 P1 C7 C8 96.5(3) .
C14 P1 C7 C8 -22.4(3) .
C13 P1 C7 C12 41.1(3) .
C1 P1 C7 C12 -84.7(3) .
C14 P1 C7 C12 156.3(3) .
C12 C7 C8 C9 -0.1(6) .
P1 C7 C8 C9 178.7(3) .
C7 C8 C9 C10 1.1(7) .
C8 C9 C10 C11 -2.1(7) .
C9 C10 C11 C12 1.9(7) .
C10 C11 C12 C7 -0.9(6) .
C8 C7 C12 C11 0.0(6) .
P1 C7 C12 C11 -178.8(3) .
C13 P1 C14 C15 -120.9(4) .
C1 P1 C14 C15 0.3(4) .
C7 P1 C14 C15 121.0(4) .
C13 P1 C14 F1 58.5(3) .
C1 P1 C14 F1 179.7(2) .
C7 P1 C14 F1 -59.6(3) .
F1 C14 C15 C15 -3.2(6) 2_566
P1 C14 C15 C15 176.1(3) 2_566
F3 C16 S1 O1 174.7(3) .
F4 C16 S1 O1 55.0(4) .
F2 C16 S1 O1 -64.5(4) .
F3 C16 S1 O3 -64.6(4) .
F4 C16 S1 O3 175.7(3) .
F2 C16 S1 O3 56.2(4) .
F3 C16 S1 O2 54.1(4) .
F4 C16 S1 O2 -65.6(4) .
F2 C16 S1 O2 174.9(4) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139125237
