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#$Date: 2019-11-24 11:35:15 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237814 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/87/4088770.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_4088770
loop_
_publ_author_name
'John, Alex'
'Miranda, Maria O.'
'Ding, Keying'
'Dereli, Büsra'
'Ortuño, Manuel A.'
'LaPointe, Anne M.'
'Coates, Geoffrey W.'
'Cramer, Christopher J.'
'Tolman, William B.'
_publ_section_title
;
 Nickel Catalysts for the Dehydrative Decarbonylation of Carboxylic Acids
 to Alkenes
;
_journal_issue                   14
_journal_name_full               Organometallics
_journal_page_first              2391
_journal_paper_doi               10.1021/acs.organomet.6b00415
_journal_volume                  35
_journal_year                    2016
_chemical_formula_moiety         'C55 H45 Ni O P3'
_chemical_formula_sum            'C55 H45 Ni O P3'
_chemical_formula_weight         873.51
_chemical_name_common            AJ-I-97
_chemical_name_systematic
; 
 "AJ-I-97" 
;
_space_group_IT_number           173
_space_group_name_Hall           'P 6c'
_space_group_name_H-M_alt        'P 63'
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_H-M   'P 63'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            2
_cell_length_a                   18.4755(12)
_cell_length_b                   18.4755(12)
_cell_length_c                   9.9813(6)
_cell_measurement_reflns_used    5864
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      22.264
_cell_measurement_theta_min      2.2045
_cell_volume                     2950.6(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            34833
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         1.27
_exptl_absorpt_coefficient_mu    0.440
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7001
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    0.983
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_platon_squeeze_details
;
Volume consistent with three toluene molecules
;
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.001(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         4515
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0308
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0317P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0615
_refine_ls_wR_factor_ref         0.0632
_reflns_number_gt                3992
_reflns_number_total             4515
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om6b00415_si_002.cif
_cod_data_source_block           14050sq
_cod_original_sg_symbol_H-M      P6(3)
_cod_database_code               4088770
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x-y, x, z+1/2'
'y, -x+y, z+1/2'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Ni1 Ni 0.6667 0.3333 0.78851(3) 0.02412(9) Uani 1 3 d S
P1 P 0.75586(2) 0.46363(3) 0.72836(4) 0.02490(10) Uani 1 1 d .
C13 C 0.77612(10) 0.49403(11) 0.55070(17) 0.0259(4) Uani 1 1 d .
C18 C 0.77997(11) 0.43799(11) 0.46316(17) 0.0335(4) Uani 1 1 d .
H18A H 0.7730 0.3869 0.4971 0.040 Uiso 1 1 calc R
C1 C 0.86359(9) 0.50658(9) 0.7906(2) 0.0305(3) Uani 1 1 d .
C2 C 0.87618(12) 0.48287(12) 0.9170(2) 0.0411(5) Uani 1 1 d .
H2A H 0.8296 0.4431 0.9675 0.049 Uiso 1 1 calc R
C3 C 0.95589(14) 0.51651(14) 0.9699(2) 0.0550(6) Uani 1 1 d .
H3A H 0.9635 0.4999 1.0564 0.066 Uiso 1 1 calc R
C4 C 1.02412(14) 0.57399(15) 0.8976(2) 0.0584(6) Uani 1 1 d .
H4A H 1.0787 0.5978 0.9344 0.070 Uiso 1 1 calc R
C5 C 1.01249(12) 0.59628(14) 0.7730(3) 0.0589(6) Uani 1 1 d .
H5A H 1.0594 0.6349 0.7219 0.071 Uiso 1 1 calc R
C6 C 0.93204(11) 0.56285(11) 0.7193(2) 0.0409(4) Uani 1 1 d .
H6A H 0.9249 0.5794 0.6324 0.049 Uiso 1 1 calc R
C7 C 0.73182(10) 0.54183(10) 0.7959(2) 0.0327(4) Uani 1 1 d .
C8 C 0.77717(15) 0.59545(13) 0.9003(2) 0.0527(6) Uani 1 1 d .
H8A H 0.8233 0.5930 0.9373 0.063 Uiso 1 1 calc R
C9 C 0.75618(18) 0.65197(16) 0.9507(3) 0.0724(8) Uani 1 1 d .
H9A H 0.7875 0.6881 1.0221 0.087 Uiso 1 1 calc R
C10 C 0.68861(17) 0.65591(15) 0.8962(2) 0.0655(7) Uani 1 1 d .
H10A H 0.6739 0.6948 0.9306 0.079 Uiso 1 1 calc R
C11 C 0.64423(12) 0.60451(12) 0.7947(3) 0.0528(5) Uani 1 1 d .
H11A H 0.5987 0.6078 0.7572 0.063 Uiso 1 1 calc R
C12 C 0.66455(11) 0.54708(11) 0.7450(2) 0.0404(5) Uani 1 1 d .
H12A H 0.6320 0.5105 0.6749 0.048 Uiso 1 1 calc R
C14 C 0.78631(11) 0.56867(12) 0.4972(2) 0.0374(4) Uani 1 1 d .
H14A H 0.7849 0.6089 0.5546 0.045 Uiso 1 1 calc R
C15 C 0.79850(13) 0.58385(14) 0.3610(2) 0.0504(5) Uani 1 1 d .
H15A H 0.8044 0.6343 0.3259 0.060 Uiso 1 1 calc R
C16 C 0.80228(11) 0.52821(13) 0.2761(2) 0.0472(5) Uani 1 1 d .
H16A H 0.8107 0.5398 0.1829 0.057 Uiso 1 1 calc R
C17 C 0.79373(11) 0.45462(12) 0.32655(18) 0.0422(5) Uani 1 1 d .
H17A H 0.7972 0.4157 0.2685 0.051 Uiso 1 1 calc R
C19 C 0.6667 0.3333 0.9636(3) 0.0368(8) Uani 1 3 d S
O1 O 0.6667 0.3333 1.0795(2) 0.0631(8) Uani 1 3 d S
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'
P P 0.1023 0.0942 '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'
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
C19 Ni1 P1 105.731(15) . 4_655
C19 Ni1 P1 105.731(15) . .
P1 Ni1 P1 112.939(12) 4_655 .
C19 Ni1 P1 105.730(14) . 5_665
P1 Ni1 P1 112.937(12) 4_655 5_665
P1 Ni1 P1 112.939(12) . 5_665
C7 P1 C13 101.87(8) . .
C7 P1 C1 99.86(8) . .
C13 P1 C1 100.49(9) . .
C7 P1 Ni1 114.45(6) . .
C13 P1 Ni1 121.33(6) . .
C1 P1 Ni1 115.66(6) . .
C18 C13 C14 117.66(16) . .
C18 C13 P1 117.30(13) . .
C14 C13 P1 125.03(13) . .
C13 C18 C17 121.68(17) . .
C13 C18 H18A 119.2 . .
C17 C18 H18A 119.2 . .
C6 C1 C2 118.28(17) . .
C6 C1 P1 122.74(16) . .
C2 C1 P1 118.95(14) . .
C3 C2 C1 120.8(2) . .
C3 C2 H2A 119.6 . .
C1 C2 H2A 119.6 . .
C4 C3 C2 120.2(2) . .
C4 C3 H3A 119.9 . .
C2 C3 H3A 119.9 . .
C5 C4 C3 119.33(19) . .
C5 C4 H4A 120.3 . .
C3 C4 H4A 120.3 . .
C4 C5 C6 120.7(2) . .
C4 C5 H5A 119.7 . .
C6 C5 H5A 119.7 . .
C1 C6 C5 120.7(2) . .
C1 C6 H6A 119.7 . .
C5 C6 H6A 119.7 . .
C12 C7 C8 117.69(17) . .
C12 C7 P1 119.76(14) . .
C8 C7 P1 122.53(14) . .
C9 C8 C7 121.0(2) . .
C9 C8 H8A 119.5 . .
C7 C8 H8A 119.5 . .
C8 C9 C10 119.7(2) . .
C8 C9 H9A 120.2 . .
C10 C9 H9A 120.2 . .
C11 C10 C9 120.0(2) . .
C11 C10 H10A 120.0 . .
C9 C10 H10A 120.0 . .
C10 C11 C12 120.4(2) . .
C10 C11 H11A 119.8 . .
C12 C11 H11A 119.8 . .
C11 C12 C7 121.2(2) . .
C11 C12 H12A 119.4 . .
C7 C12 H12A 119.4 . .
C15 C14 C13 120.13(19) . .
C15 C14 H14A 119.9 . .
C13 C14 H14A 119.9 . .
C16 C15 C14 121.6(2) . .
C16 C15 H15A 119.2 . .
C14 C15 H15A 119.2 . .
C15 C16 C17 119.48(19) . .
C15 C16 H16A 120.3 . .
C17 C16 H16A 120.3 . .
C16 C17 C18 119.46(19) . .
C16 C17 H17A 120.3 . .
C18 C17 H17A 120.3 . .
O1 C19 Ni1 180.000(1) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 C19 1.748(3) .
Ni1 P1 2.2145(4) 4_655
Ni1 P1 2.2145(5) .
Ni1 P1 2.2146(4) 5_665
P1 C7 1.8388(17) .
P1 C13 1.8411(17) .
P1 C1 1.8432(16) .
C13 C18 1.384(2) .
C13 C14 1.401(2) .
C18 C17 1.393(2) .
C18 H18A 0.9500 .
C1 C6 1.368(3) .
C1 C2 1.393(3) .
C2 C3 1.385(3) .
C2 H2A 0.9500 .
C3 C4 1.378(3) .
C3 H3A 0.9500 .
C4 C5 1.361(3) .
C4 H4A 0.9500 .
C5 C6 1.400(3) .
C5 H5A 0.9500 .
C6 H6A 0.9500 .
C7 C12 1.390(2) .
C7 C8 1.392(3) .
C8 C9 1.378(3) .
C8 H8A 0.9500 .
C9 C10 1.396(3) .
C9 H9A 0.9500 .
C10 C11 1.350(3) .
C10 H10A 0.9500 .
C11 C12 1.382(3) .
C11 H11A 0.9500 .
C12 H12A 0.9500 .
C14 C15 1.384(3) .
C14 H14A 0.9500 .
C15 C16 1.361(3) .
C15 H15A 0.9500 .
C16 C17 1.383(3) .
C16 H16A 0.9500 .
C17 H17A 0.9500 .
C19 O1 1.157(4) .
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_1
C19 Ni1 P1 C7 -56.86(7) .
P1 Ni1 P1 C7 58.29(8) 4_655
P1 Ni1 P1 C7 -172.01(7) 5_665
C19 Ni1 P1 C13 -179.64(6) .
P1 Ni1 P1 C13 -64.48(6) 4_655
P1 Ni1 P1 C13 65.21(6) 5_665
C19 Ni1 P1 C1 58.42(7) .
P1 Ni1 P1 C1 173.58(7) 4_655
P1 Ni1 P1 C1 -56.73(7) 5_665
C7 P1 C13 C18 -167.28(13) .
C1 P1 C13 C18 90.19(14) .
Ni1 P1 C13 C18 -38.73(15) .
C7 P1 C13 C14 11.43(17) .
C1 P1 C13 C14 -91.09(16) .
Ni1 P1 C13 C14 139.98(13) .
C14 C13 C18 C17 0.2(3) .
P1 C13 C18 C17 179.02(14) .
C7 P1 C1 C6 -89.71(16) .
C13 P1 C1 C6 14.45(16) .
Ni1 P1 C1 C6 146.96(13) .
C7 P1 C1 C2 88.41(15) .
C13 P1 C1 C2 -167.44(14) .
Ni1 P1 C1 C2 -34.93(16) .
C6 C1 C2 C3 1.1(3) .
P1 C1 C2 C3 -177.13(15) .
C1 C2 C3 C4 -0.2(3) .
C2 C3 C4 C5 -1.1(3) .
C3 C4 C5 C6 1.4(3) .
C2 C1 C6 C5 -0.7(3) .
P1 C1 C6 C5 177.43(15) .
C4 C5 C6 C1 -0.6(3) .
C13 P1 C7 C12 60.16(16) .
C1 P1 C7 C12 163.18(15) .
Ni1 P1 C7 C12 -72.63(16) .
C13 P1 C7 C8 -121.79(17) .
C1 P1 C7 C8 -18.76(19) .
Ni1 P1 C7 C8 105.42(16) .
C12 C7 C8 C9 -0.3(3) .
P1 C7 C8 C9 -178.41(18) .
C7 C8 C9 C10 -0.2(4) .
C8 C9 C10 C11 0.0(4) .
C9 C10 C11 C12 0.8(4) .
C10 C11 C12 C7 -1.3(3) .
C8 C7 C12 C11 1.1(3) .
P1 C7 C12 C11 179.23(15) .
C18 C13 C14 C15 0.9(3) .
P1 C13 C14 C15 -177.79(15) .
C13 C14 C15 C16 -1.1(3) .
C14 C15 C16 C17 0.0(3) .
C15 C16 C17 C18 1.1(3) .
C13 C18 C17 C16 -1.2(3) .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.033 915 305 ' '
