#------------------------------------------------------------------------------
#$Date: 2019-10-28 10:14:11 +0200 (Mon, 28 Oct 2019) $
#$Revision: 219904 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/47/4514739.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_4514739
loop_
_publ_author_name
'Russell, John E. A.'
'Entz, Emily D.'
'Joyce, Ian M.'
'Neufeldt, Sharon R.'
_publ_section_title
;
 Nickel-Catalyzed Stille Cross Coupling of C-O Electrophiles.
;
_journal_issue                   4
_journal_name_full               'ACS catalysis'
_journal_page_first              3304
_journal_page_last               3310
_journal_paper_doi               10.1021/acscatal.9b00744
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C29 H42 F N Ni O3 P2 S'
_chemical_formula_sum            'C29 H42 F N Ni O3 P2 S'
_chemical_formula_weight         624.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.7950(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.6752(3)
_cell_length_b                   12.5702(4)
_cell_length_c                   14.4059(5)
_cell_measurement_reflns_used    9860
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.555
_cell_measurement_theta_min      3.009
_cell_volume                     1537.78(9)
_computing_cell_refinement       'SAINT V8.38A (BRUKER-AXS, 2016)'
_computing_data_collection       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT V8.38A (BRUKER-AXS, 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      100
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            42439
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.553
_diffrn_reflns_theta_min         2.889
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.839
_exptl_absorpt_correction_T_max  0.6468
_exptl_absorpt_correction_T_min  0.6012
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0447 before and 0.0413 after correction. The Ratio of minimum to maximum transmission is 0.9295. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       prism
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3706
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0238
_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/[σ²(Fo²)+(0.0297P)²+0.7909P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0593
_refine_ls_wR_factor_ref         0.0613
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3375
_reflns_number_total             3706
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs9b00744_si_003.cif
_cod_data_source_block           msu_sn10
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               4514739
_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_max   0.975
_shelx_estimated_absorpt_t_min   0.844
_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. Others
 Fixed Sof: H7A(0.5) H7B(0.5) H7C(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C16(H16A,H16B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
3.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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
Ni1 Ni 0.69920(2) 0.7500 0.73365(2) 0.01043(7) Uani 1 2 d S T P . .
S1 S 0.88203(5) 0.7500 0.94368(3) 0.01378(9) Uani 1 2 d S T P . .
P1 P 0.69867(3) 0.57482(2) 0.71874(2) 0.01141(8) Uani 1 1 d . . . . .
F1 F 0.08810(15) 0.7500 0.44130(9) 0.0356(3) Uani 1 2 d S T P . .
O1 O 0.88117(14) 0.7500 0.83933(8) 0.0140(2) Uani 1 2 d S T P . .
O2 O 0.81739(11) 0.65290(7) 0.97325(6) 0.0209(2) Uani 1 1 d . . . . .
N1 N 1.07031(18) 0.7500 0.99638(10) 0.0170(3) Uani 1 2 d S T P . .
C1 C 0.5120(2) 0.7500 0.63800(12) 0.0132(3) Uani 1 2 d S T P . .
C2 C 0.3670(2) 0.7500 0.66784(13) 0.0165(3) Uani 1 2 d S T P . .
C3 C 0.2255(2) 0.7500 0.60078(15) 0.0221(4) Uani 1 2 d S T P . .
H3 H 0.1277 0.7500 0.6209 0.027 Uiso 1 2 calc RS T P . .
C4 C 0.2282(2) 0.7500 0.50568(14) 0.0225(4) Uani 1 2 d S T P . .
C5 C 0.3663(2) 0.7500 0.47270(13) 0.0194(4) Uani 1 2 d S T P . .
H5 H 0.3657 0.7500 0.4067 0.023 Uiso 1 2 calc RS T P . .
C6 C 0.5072(2) 0.7500 0.53976(12) 0.0147(3) Uani 1 2 d S T P . .
H6 H 0.6037 0.7500 0.5183 0.018 Uiso 1 2 calc RS T P . .
C7 C 0.3585(2) 0.7500 0.77126(14) 0.0229(4) Uani 1 2 d S T P . .
H7A H 0.3291 0.8211 0.7895 0.034 Uiso 0.5 1 calc GR . . A -1
H7B H 0.4615 0.7306 0.8095 0.034 Uiso 0.5 1 calc GR . . A -1
H7C H 0.2794 0.6983 0.7820 0.034 Uiso 0.5 1 calc GR . . A -1
C8 C 0.53196(14) 0.50633(10) 0.75037(9) 0.0150(2) Uani 1 1 d . . . . .
C9 C 0.41107(17) 0.46073(13) 0.68404(10) 0.0266(3) Uani 1 1 d . . . . .
H9 H 0.4117 0.4662 0.6184 0.032 Uiso 1 1 calc R . . . .
C10 C 0.28897(19) 0.40700(16) 0.71336(12) 0.0376(4) Uani 1 1 d . . . . .
H10 H 0.2063 0.3765 0.6676 0.045 Uiso 1 1 calc R . . . .
C11 C 0.28777(17) 0.39790(14) 0.80892(11) 0.0313(3) Uani 1 1 d . . . . .
H11 H 0.2057 0.3598 0.8288 0.038 Uiso 1 1 calc R . . . .
C12 C 0.40590(17) 0.44420(12) 0.87524(10) 0.0261(3) Uani 1 1 d . . . . .
H12 H 0.4044 0.4386 0.9408 0.031 Uiso 1 1 calc R . . . .
C13 C 0.52669(16) 0.49884(11) 0.84655(9) 0.0217(3) Uani 1 1 d . . . . .
H13 H 0.6067 0.5315 0.8926 0.026 Uiso 1 1 calc R . . . .
C14 C 0.86664(14) 0.50619(10) 0.79206(9) 0.0155(2) Uani 1 1 d . . . . .
H14A H 0.9649 0.5356 0.7775 0.019 Uiso 1 1 calc R . . . .
H14B H 0.8674 0.5215 0.8596 0.019 Uiso 1 1 calc R . . . .
C15 C 0.86646(16) 0.38552(10) 0.77820(9) 0.0204(3) Uani 1 1 d . . . . .
H15A H 0.8960 0.3690 0.7177 0.031 Uiso 1 1 calc GR . . . .
H15B H 0.7609 0.3575 0.7779 0.031 Uiso 1 1 calc GR . . . .
H15C H 0.9423 0.3528 0.8302 0.031 Uiso 1 1 calc GR . . . .
C16 C 0.70239(15) 0.52825(10) 0.59899(8) 0.0155(2) Uani 1 1 d . . . . .
H16A H 0.6969 0.4496 0.5976 0.019 Uiso 1 1 calc R . . . .
H16B H 0.6087 0.5559 0.5544 0.019 Uiso 1 1 calc R . . . .
C17 C 0.85115(16) 0.56420(13) 0.56628(10) 0.0253(3) Uani 1 1 d . . . . .
H17A H 0.8487 0.5376 0.5021 0.038 Uiso 1 1 calc GR . . . .
H17B H 0.9441 0.5360 0.6096 0.038 Uiso 1 1 calc GR . . . .
H17C H 0.8559 0.6421 0.5662 0.038 Uiso 1 1 calc GR . . . .
C18 C 1.15546(17) 0.84692(11) 0.97966(10) 0.0233(3) Uani 1 1 d . . . . .
H18A H 1.1655 0.8493 0.9132 0.035 Uiso 1 1 calc GR . . . .
H18B H 1.2605 0.8466 1.0208 0.035 Uiso 1 1 calc GR . . . .
H18C H 1.0971 0.9096 0.9939 0.035 Uiso 1 1 calc GR . . . .
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 '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'
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
P1 Ni1 P1 168.902(18) . 4_575
O1 Ni1 P1 93.491(10) . 4_575
O1 Ni1 P1 93.491(10) . .
C1 Ni1 P1 86.856(10) . 4_575
C1 Ni1 P1 86.856(10) . .
C1 Ni1 O1 175.53(6) . .
O1 S1 N1 105.17(7) . .
O2 S1 O1 111.88(4) . .
O2 S1 O1 111.88(4) 4_575 .
O2 S1 O2 115.48(8) . 4_575
O2 S1 N1 105.74(5) 4_575 .
O2 S1 N1 105.74(5) . .
C8 P1 Ni1 115.64(4) . .
C8 P1 C14 102.25(6) . .
C8 P1 C16 104.66(6) . .
C14 P1 Ni1 115.29(4) . .
C16 P1 Ni1 114.22(4) . .
C16 P1 C14 103.17(6) . .
S1 O1 Ni1 128.10(8) . .
C18 N1 S1 114.01(8) . .
C18 N1 S1 114.01(8) 4_575 .
C18 N1 C18 111.96(15) . 4_575
C2 C1 Ni1 117.49(13) . .
C6 C1 Ni1 125.04(13) . .
C6 C1 C2 117.47(16) . .
C1 C2 C7 121.90(16) . .
C3 C2 C1 120.09(17) . .
C3 C2 C7 118.01(17) . .
C2 C3 H3 120.1 . .
C4 C3 C2 119.78(18) . .
C4 C3 H3 120.1 . .
F1 C4 C3 118.74(18) . .
F1 C4 C5 118.74(18) . .
C3 C4 C5 122.52(17) . .
C4 C5 H5 121.2 . .
C4 C5 C6 117.54(17) . .
C6 C5 H5 121.2 . .
C1 C6 H6 118.7 . .
C5 C6 C1 122.59(17) . .
C5 C6 H6 118.7 . .
C2 C7 H7A 109.5 . .
C2 C7 H7B 109.5 . .
C2 C7 H7C 109.5 . .
H7A C7 H7B 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C9 C8 P1 123.34(10) . .
C9 C8 C13 118.71(12) . .
C13 C8 P1 117.94(10) . .
C8 C9 H9 119.8 . .
C8 C9 C10 120.35(13) . .
C10 C9 H9 119.8 . .
C9 C10 H10 119.9 . .
C11 C10 C9 120.18(14) . .
C11 C10 H10 119.9 . .
C10 C11 H11 120.0 . .
C12 C11 C10 119.92(14) . .
C12 C11 H11 120.0 . .
C11 C12 H12 119.9 . .
C11 C12 C13 120.21(13) . .
C13 C12 H12 119.9 . .
C8 C13 H13 119.7 . .
C12 C13 C8 120.59(13) . .
C12 C13 H13 119.7 . .
P1 C14 H14A 108.7 . .
P1 C14 H14B 108.7 . .
H14A C14 H14B 107.6 . .
C15 C14 P1 114.35(9) . .
C15 C14 H14A 108.7 . .
C15 C14 H14B 108.7 . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15B 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
P1 C16 H16A 109.2 . .
P1 C16 H16B 109.2 . .
H16A C16 H16B 107.9 . .
C17 C16 P1 112.01(9) . .
C17 C16 H16A 109.2 . .
C17 C16 H16B 109.2 . .
C16 C17 H17A 109.5 . .
C16 C17 H17B 109.5 . .
C16 C17 H17C 109.5 . .
H17A C17 H17B 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
N1 C18 H18A 109.5 . .
N1 C18 H18B 109.5 . .
N1 C18 H18C 109.5 . .
H18A C18 H18B 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 P1 2.2124(3) 4_575
Ni1 P1 2.2124(3) .
Ni1 O1 1.9563(12) .
Ni1 C1 1.9027(17) .
S1 O1 1.5018(12) .
S1 O2 1.4434(9) 4_575
S1 O2 1.4434(9) .
S1 N1 1.6545(16) .
P1 C8 1.8193(13) .
P1 C14 1.8314(12) .
P1 C16 1.8283(12) .
F1 C4 1.370(2) .
N1 C18 1.4699(16) .
N1 C18 1.4700(16) 4_575
C1 C2 1.411(2) .
C1 C6 1.407(2) .
C2 C3 1.399(3) .
C2 C7 1.507(2) .
C3 H3 0.9500 .
C3 C4 1.375(3) .
C4 C5 1.376(3) .
C5 H5 0.9500 .
C5 C6 1.394(2) .
C6 H6 0.9500 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 C9 1.3899(18) .
C8 C13 1.3987(17) .
C9 H9 0.9500 .
C9 C10 1.393(2) .
C10 H10 0.9500 .
C10 C11 1.384(2) .
C11 H11 0.9500 .
C11 C12 1.379(2) .
C12 H12 0.9500 .
C12 C13 1.3848(19) .
C13 H13 0.9500 .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C14 C15 1.5298(18) .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C16 C17 1.5298(18) .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
