#------------------------------------------------------------------------------
#$Date: 2017-03-04 07:13:00 +0200 (Sat, 04 Mar 2017) $
#$Revision: 193135 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/57/4125759.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_4125759
loop_
_publ_author_name
'Mohadjer Beromi, Megan'
'Nova, Ainara'
'Balcells, David'
'Brasacchio, Ann M.'
'Brudvig, Gary W.'
'Guard, Louise M.'
'Hazari, Nilay'
'Vinyard, David J.'
_publ_contact_author
;
 Prof. Nilay Hazari         
 The Department of Chemistry 
 Yale University 
 P. O. Box 208107 
 New Haven 
 Connecticut 06520 USA.
;
_publ_section_title
;
 Mechanistic Study of an Improved Ni Precatalyst for Suzuki-Miyaura
 Reactions of Aryl Sulfamates: Understanding the Role of Ni(I) Species.
;
_journal_issue                   2
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              922
_journal_page_last               936
_journal_paper_doi               10.1021/jacs.6b11412
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C36 H66 Cl Ni P2'
_chemical_formula_sum            'C36 H66 Cl Ni P2'
_chemical_formula_weight         654.98
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 97.617(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.6551(8)
_cell_length_b                   9.0738(2)
_cell_length_c                   21.9618(15)
_cell_measurement_reflns_used    27453
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      25.4
_cell_measurement_theta_min      3.1
_cell_volume                     3487.2(3)
_computing_cell_refinement
'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction
'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_molecular_graphics
;
Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H., 
OLEX2: A complete structure solution, refinement and analysis program
(2009). J. Appl. Cryst., 42, 339-341.
;
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID imaging plate'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            33469
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         3.053
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    0.748
_exptl_absorpt_correction_T_max  0.943
_exptl_absorpt_correction_T_min  0.825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1428
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.657
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3183
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0259
_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)+(0.0315P)²+4.1143P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0642
_refine_ls_wR_factor_ref         0.0653
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2961
_reflns_number_total             3183
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja6b11412_si_002.cif
_cod_data_source_block           '_PCyNiICl'
_cod_database_code               4125759
_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   0.796
_shelx_estimated_absorpt_t_max   0.943
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
Ni1 Ni 0.5000 0.15213(3) 0.2500 0.01399(9) Uani 1 2 d S T P
Cl1 Cl 0.5000 -0.08904(6) 0.2500 0.02296(13) Uani 1 2 d S T P
P1 P 0.55844(2) 0.27276(4) 0.33255(2) 0.01287(10) Uani 1 1 d . . .
C1 C 0.58476(9) 0.12478(16) 0.39093(7) 0.0152(3) Uani 1 1 d . . .
H1 H 0.5383 0.0610 0.3889 0.018 Uiso 1 1 calc R U .
C2 C 0.60350(10) 0.16725(17) 0.45902(7) 0.0194(3) Uani 1 1 d . . .
H2A H 0.6515 0.2249 0.4652 0.023 Uiso 1 1 calc R U .
H2B H 0.5620 0.2295 0.4713 0.023 Uiso 1 1 calc R U .
C3 C 0.61229(10) 0.02790(18) 0.49908(7) 0.0213(4) Uani 1 1 d . . .
H3A H 0.6266 0.0567 0.5426 0.026 Uiso 1 1 calc R U .
H3B H 0.5626 -0.0242 0.4957 0.026 Uiso 1 1 calc R U .
C4 C 0.67277(9) -0.07638(18) 0.48013(7) 0.0208(3) Uani 1 1 d . . .
H4A H 0.7236 -0.0290 0.4881 0.025 Uiso 1 1 calc R U .
H4B H 0.6741 -0.1675 0.5050 0.025 Uiso 1 1 calc R U .
C5 C 0.65532(9) -0.11534(17) 0.41218(7) 0.0203(3) Uani 1 1 d . . .
H5A H 0.6072 -0.1726 0.4051 0.024 Uiso 1 1 calc R U .
H5B H 0.6969 -0.1776 0.4001 0.024 Uiso 1 1 calc R U .
C6 C 0.64749(9) 0.02346(17) 0.37253(7) 0.0165(3) Uani 1 1 d . . .
H6A H 0.6349 -0.0046 0.3288 0.020 Uiso 1 1 calc R U .
H6B H 0.6968 0.0770 0.3773 0.020 Uiso 1 1 calc R U .
C7 C 0.64463(8) 0.37961(16) 0.31940(7) 0.0141(3) Uani 1 1 d . . .
H7 H 0.6245 0.4651 0.2934 0.017 Uiso 1 1 calc R U .
C8 C 0.69265(9) 0.44907(17) 0.37539(7) 0.0168(3) Uani 1 1 d . . .
H8A H 0.7170 0.3705 0.4025 0.020 Uiso 1 1 calc R U .
H8B H 0.6592 0.5075 0.3990 0.020 Uiso 1 1 calc R U .
C9 C 0.75445(9) 0.54920(17) 0.35447(7) 0.0181(3) Uani 1 1 d . . .
H9A H 0.7298 0.6312 0.3295 0.022 Uiso 1 1 calc R U .
H9B H 0.7857 0.5921 0.3909 0.022 Uiso 1 1 calc R U .
C10 C 0.80576(9) 0.46325(18) 0.31676(8) 0.0203(3) Uani 1 1 d . . .
H10A H 0.8330 0.3853 0.3426 0.024 Uiso 1 1 calc R U .
H10B H 0.8444 0.5303 0.3031 0.024 Uiso 1 1 calc R U .
C11 C 0.75902(10) 0.39344(18) 0.26095(8) 0.0224(4) Uani 1 1 d . . .
H11A H 0.7931 0.3341 0.2382 0.027 Uiso 1 1 calc R U .
H11B H 0.7359 0.4719 0.2332 0.027 Uiso 1 1 calc R U .
C12 C 0.69592(9) 0.29496(18) 0.27986(7) 0.0188(3) Uani 1 1 d . . .
H12A H 0.7193 0.2096 0.3034 0.023 Uiso 1 1 calc R U .
H12B H 0.6643 0.2569 0.2426 0.023 Uiso 1 1 calc R U .
C13 C 0.50598(8) 0.40524(16) 0.37573(7) 0.0136(3) Uani 1 1 d . . .
H13 H 0.5384 0.4245 0.4158 0.016 Uiso 1 1 calc R U .
C14 C 0.43048(9) 0.33840(17) 0.39029(8) 0.0188(3) Uani 1 1 d . . .
H14A H 0.3974 0.3158 0.3514 0.023 Uiso 1 1 calc R U .
H14B H 0.4411 0.2449 0.4131 0.023 Uiso 1 1 calc R U .
C15 C 0.38852(9) 0.44405(18) 0.42873(8) 0.0210(3) Uani 1 1 d . . .
H15A H 0.3387 0.4007 0.4350 0.025 Uiso 1 1 calc R U .
H15B H 0.4190 0.4575 0.4695 0.025 Uiso 1 1 calc R U .
C16 C 0.37536(9) 0.59370(18) 0.39731(8) 0.0199(3) Uani 1 1 d . . .
H16A H 0.3398 0.5821 0.3588 0.024 Uiso 1 1 calc R U .
H16B H 0.3516 0.6617 0.4245 0.024 Uiso 1 1 calc R U .
C17 C 0.45044(9) 0.65940(17) 0.38272(8) 0.0194(3) Uani 1 1 d . . .
H17A H 0.4841 0.6799 0.4215 0.023 Uiso 1 1 calc R U .
H17B H 0.4401 0.7539 0.3607 0.023 Uiso 1 1 calc R U .
C18 C 0.49108(9) 0.55457(17) 0.34321(7) 0.0172(3) Uani 1 1 d . . .
H18A H 0.5402 0.5985 0.3355 0.021 Uiso 1 1 calc R U .
H18B H 0.4591 0.5397 0.3031 0.021 Uiso 1 1 calc R U .
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'
Cl Cl 0.1484 0.1585 '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'
P P 0.1023 0.0942 '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
Cl1 Ni1 P1 119.139(11) . 2_655
Cl1 Ni1 P1 119.138(11) . .
P1 Ni1 P1 121.72(2) 2_655 .
C13 P1 C7 102.48(7) . .
C13 P1 C1 102.14(7) . .
C7 P1 C1 110.27(7) . .
C13 P1 Ni1 121.43(5) . .
C7 P1 Ni1 115.23(5) . .
C1 P1 Ni1 104.40(5) . .
C6 C1 C2 109.67(12) . .
C6 C1 P1 111.83(10) . .
C2 C1 P1 119.23(11) . .
C6 C1 H1 104.9 . .
C2 C1 H1 104.9 . .
P1 C1 H1 104.9 . .
C3 C2 C1 110.07(13) . .
C3 C2 H2A 109.6 . .
C1 C2 H2A 109.6 . .
C3 C2 H2B 109.6 . .
C1 C2 H2B 109.6 . .
H2A C2 H2B 108.2 . .
C4 C3 C2 112.05(13) . .
C4 C3 H3A 109.2 . .
C2 C3 H3A 109.2 . .
C4 C3 H3B 109.2 . .
C2 C3 H3B 109.2 . .
H3A C3 H3B 107.9 . .
C5 C4 C3 110.67(13) . .
C5 C4 H4A 109.5 . .
C3 C4 H4A 109.5 . .
C5 C4 H4B 109.5 . .
C3 C4 H4B 109.5 . .
H4A C4 H4B 108.1 . .
C4 C5 C6 110.99(13) . .
C4 C5 H5A 109.4 . .
C6 C5 H5A 109.4 . .
C4 C5 H5B 109.4 . .
C6 C5 H5B 109.4 . .
H5A C5 H5B 108.0 . .
C5 C6 C1 110.98(12) . .
C5 C6 H6A 109.4 . .
C1 C6 H6A 109.4 . .
C5 C6 H6B 109.4 . .
C1 C6 H6B 109.4 . .
H6A C6 H6B 108.0 . .
C8 C7 C12 110.68(12) . .
C8 C7 P1 117.82(10) . .
C12 C7 P1 112.46(10) . .
C8 C7 H7 104.8 . .
C12 C7 H7 104.8 . .
P1 C7 H7 104.8 . .
C7 C8 C9 110.02(12) . .
C7 C8 H8A 109.7 . .
C9 C8 H8A 109.7 . .
C7 C8 H8B 109.7 . .
C9 C8 H8B 109.7 . .
H8A C8 H8B 108.2 . .
C10 C9 C8 110.94(13) . .
C10 C9 H9A 109.5 . .
C8 C9 H9A 109.5 . .
C10 C9 H9B 109.5 . .
C8 C9 H9B 109.5 . .
H9A C9 H9B 108.0 . .
C9 C10 C11 110.70(13) . .
C9 C10 H10A 109.5 . .
C11 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
C11 C10 H10B 109.5 . .
H10A C10 H10B 108.1 . .
C10 C11 C12 111.19(13) . .
C10 C11 H11A 109.4 . .
C12 C11 H11A 109.4 . .
C10 C11 H11B 109.4 . .
C12 C11 H11B 109.4 . .
H11A C11 H11B 108.0 . .
C11 C12 C7 111.46(13) . .
C11 C12 H12A 109.3 . .
C7 C12 H12A 109.3 . .
C11 C12 H12B 109.3 . .
C7 C12 H12B 109.3 . .
H12A C12 H12B 108.0 . .
C14 C13 C18 110.17(12) . .
C14 C13 P1 110.90(10) . .
C18 C13 P1 113.58(10) . .
C14 C13 H13 107.3 . .
C18 C13 H13 107.3 . .
P1 C13 H13 107.3 . .
C15 C14 C13 111.34(13) . .
C15 C14 H14A 109.4 . .
C13 C14 H14A 109.4 . .
C15 C14 H14B 109.4 . .
C13 C14 H14B 109.4 . .
H14A C14 H14B 108.0 . .
C16 C15 C14 111.31(13) . .
C16 C15 H15A 109.4 . .
C14 C15 H15A 109.4 . .
C16 C15 H15B 109.4 . .
C14 C15 H15B 109.4 . .
H15A C15 H15B 108.0 . .
C17 C16 C15 110.97(13) . .
C17 C16 H16A 109.4 . .
C15 C16 H16A 109.4 . .
C17 C16 H16B 109.4 . .
C15 C16 H16B 109.4 . .
H16A C16 H16B 108.0 . .
C16 C17 C18 111.24(13) . .
C16 C17 H17A 109.4 . .
C18 C17 H17A 109.4 . .
C16 C17 H17B 109.4 . .
C18 C17 H17B 109.4 . .
H17A C17 H17B 108.0 . .
C17 C18 C13 110.41(12) . .
C17 C18 H18A 109.6 . .
C13 C18 H18A 109.6 . .
C17 C18 H18B 109.6 . .
C13 C18 H18B 109.6 . .
H18A C18 H18B 108.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 Cl1 2.1883(6) .
Ni1 P1 2.2480(4) 2_655
Ni1 P1 2.2481(4) .
P1 C13 1.8534(15) .
P1 C7 1.8588(15) .
P1 C1 1.8720(15) .
C1 C6 1.534(2) .
C1 C2 1.537(2) .
C1 H1 1.0000 .
C2 C3 1.536(2) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C4 1.525(2) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 C5 1.525(2) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.527(2) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.534(2) .
C7 C12 1.540(2) .
C7 H7 1.0000 .
C8 C9 1.536(2) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.521(2) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C11 1.522(2) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.528(2) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.536(2) .
C13 C18 1.538(2) .
C13 H13 1.0000 .
C14 C15 1.532(2) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C16 1.527(2) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C17 1.526(2) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 C18 1.529(2) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
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
C13 P1 C1 C6 -164.00(11)
C7 P1 C1 C6 -55.63(12)
Ni1 P1 C1 C6 68.70(11)
C13 P1 C1 C2 -34.24(13)
C7 P1 C1 C2 74.13(13)
Ni1 P1 C1 C2 -161.53(11)
C6 C1 C2 C3 -57.17(17)
P1 C1 C2 C3 172.10(11)
C1 C2 C3 C4 56.42(18)
C2 C3 C4 C5 -55.27(19)
C3 C4 C5 C6 55.39(18)
C4 C5 C6 C1 -57.71(17)
C2 C1 C6 C5 58.44(17)
P1 C1 C6 C5 -166.99(11)
C13 P1 C7 C8 53.22(13)
C1 P1 C7 C8 -54.93(13)
Ni1 P1 C7 C8 -172.78(9)
C13 P1 C7 C12 -176.22(11)
C1 P1 C7 C12 75.63(12)
Ni1 P1 C7 C12 -42.22(12)
C12 C7 C8 C9 56.24(16)
P1 C7 C8 C9 -172.39(10)
C7 C8 C9 C10 -58.09(16)
C8 C9 C10 C11 58.05(17)
C9 C10 C11 C12 -56.28(17)
C10 C11 C12 C7 55.03(18)
C8 C7 C12 C11 -55.18(17)
P1 C7 C12 C11 170.73(11)
C7 P1 C13 C14 178.78(10)
C1 P1 C13 C14 -66.97(12)
Ni1 P1 C13 C14 48.48(12)
C7 P1 C13 C18 54.07(12)
C1 P1 C13 C18 168.32(11)
Ni1 P1 C13 C18 -76.23(12)
C18 C13 C14 C15 -56.19(17)
P1 C13 C14 C15 177.19(11)
C13 C14 C15 C16 55.37(18)
C14 C15 C16 C17 -55.04(18)
C15 C16 C17 C18 56.42(18)
C16 C17 C18 C13 -57.58(17)
C14 C13 C18 C17 57.07(17)
P1 C13 C18 C17 -177.83(11)
