#------------------------------------------------------------------------------
#$Date: 2017-12-11 01:28:22 +0200 (Mon, 11 Dec 2017) $
#$Revision: 204147 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/67/4126759.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_4126759
loop_
_publ_author_name
'Saper, Noam I.'
'Hartwig, John F.'
_publ_section_title
;
 Mechanistic Investigations of the Hydrogenolysis of Diaryl Ethers
 Catalyzed by Nickel Complexes of N-Heterocyclic Carbene Ligands.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b10537
_journal_year                    2017
_chemical_formula_sum            'C39 H48 N2 Ni O'
_chemical_formula_weight         619.50
_chemical_name_common            Compound15
_chemical_name_systematic        Compound15
_space_group.centring_type       P
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.429(4)
_cell_length_b                   16.960(3)
_cell_length_c                   9.3624(14)
_cell_measurement_reflns_used    6475
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.41
_cell_measurement_theta_min      2.48
_cell_volume                     3402.6(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-2016
_computing_structure_solution    SHELXT-2014
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_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  0.2026
_diffrn_reflns_av_unetI/netI     0.1240
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_refln_scan_rate          30
_diffrn_refln_scan_width         2.0
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            45124
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.544
_diffrn_reflns_theta_min         1.901
_diffrn_source                   'microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.602
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_description       plate
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.756
_refine_diff_density_min         -0.858
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       0.0011(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3259
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1875
_refine_ls_R_factor_gt           0.0801
_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)+(0.0998P)²+10.4191P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1825
_refine_ls_wR_factor_ref         0.2491
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1661
_reflns_number_total             3259
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b10537_si_001.cif
_cod_data_source_block           Compound15
_cod_depositor_comments
;
The following automatic conversions were performed:

'_space_group.centring_type' value 'primitive' was replaced with the
value 'P' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5642 2017-10-24 12:04:52Z antanas 
;
_cod_original_cell_volume        3402.7(10)
_cod_database_code               4126759
#BEGIN Tags that were not found in dictionaries:
_shelx_shelxl_version_number     2016/6
_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   0.976
_shelx_estimated_absorpt_t_max   0.988
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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
C1 C 0.4121(3) 0.750000 0.1997(10) 0.034(2) Uani 1 2 d S T P
C2 C 0.4282(3) 0.7056(4) -0.0394(7) 0.0460(17) Uani 1 1 d . . .
H2A H 0.394129 0.684423 -0.099624 0.055 Uiso 1 1 calc R U .
H2B H 0.468577 0.684428 -0.073629 0.055 Uiso 1 1 calc R U .
C3 C 0.4158(4) 0.6077(4) 0.1652(7) 0.059(2) Uani 1 1 d . . .
C4 C 0.3584(5) 0.5696(5) 0.1725(8) 0.069(3) Uani 1 1 d . . .
C5 C 0.3564(6) 0.4941(5) 0.2332(9) 0.101(4) Uani 1 1 d . . .
H5 H 0.318209 0.465890 0.238829 0.122 Uiso 1 1 calc R U .
C6 C 0.4121(10) 0.4609(8) 0.2857(15) 0.148(8) Uani 1 1 d . . .
H6 H 0.410911 0.411083 0.332121 0.178 Uiso 1 1 calc R U .
C7 C 0.4662(8) 0.4980(8) 0.2714(13) 0.130(7) Uani 1 1 d . . .
H7 H 0.502828 0.472062 0.303930 0.156 Uiso 1 1 calc R U .
C8 C 0.4724(6) 0.5729(5) 0.2113(8) 0.085(3) Uani 1 1 d . . .
C9 C 0.2993(4) 0.6062(4) 0.1115(8) 0.064(2) Uani 1 1 d . . .
H9 H 0.312157 0.658726 0.072624 0.077 Uiso 1 1 calc R U .
C10 C 0.2748(9) 0.5613(8) -0.0118(16) 0.247(11) Uani 1 1 d . . .
H10A H 0.308347 0.552737 -0.081205 0.371 Uiso 1 1 calc R U .
H10B H 0.258816 0.510347 0.021113 0.371 Uiso 1 1 calc R U .
H10C H 0.240985 0.591211 -0.056945 0.371 Uiso 1 1 calc R U .
C11 C 0.2532(4) 0.6231(7) 0.2240(10) 0.106(4) Uani 1 1 d . . .
H11A H 0.273220 0.652846 0.301169 0.158 Uiso 1 1 calc R U .
H11B H 0.218927 0.654271 0.183831 0.158 Uiso 1 1 calc R U .
H11C H 0.236758 0.573406 0.261889 0.158 Uiso 1 1 calc R U .
C12 C 0.5351(5) 0.6127(6) 0.1960(10) 0.098(4) Uani 1 1 d . . .
H12 H 0.528324 0.662494 0.140910 0.118 Uiso 1 1 calc R U .
C13 C 0.5822(6) 0.5642(6) 0.1145(10) 0.128(5) Uani 1 1 d . . .
H13A H 0.621641 0.593192 0.108324 0.193 Uiso 1 1 calc R U .
H13B H 0.589025 0.514097 0.164132 0.193 Uiso 1 1 calc R U .
H13C H 0.566390 0.553870 0.018041 0.193 Uiso 1 1 calc R U .
C14 C 0.5630(5) 0.6359(12) 0.3409(12) 0.243(12) Uani 1 1 d . . .
H14A H 0.532635 0.667403 0.394407 0.365 Uiso 1 1 calc R U .
H14B H 0.573145 0.588134 0.395139 0.365 Uiso 1 1 calc R U .
H14C H 0.601030 0.666848 0.325771 0.365 Uiso 1 1 calc R U .
C15 C 0.4519(5) 0.750000 0.5874(11) 0.076(4) Uani 1 2 d S T P
H15 H 0.495640 0.750000 0.603268 0.092 Uiso 1 2 calc R U P
C16 C 0.4191(5) 0.8218(6) 0.5755(8) 0.076(3) Uani 1 1 d . . .
H16 H 0.440786 0.870469 0.583068 0.091 Uiso 1 1 calc R U .
C17 C 0.3555(5) 0.8214(5) 0.5529(9) 0.076(3) Uani 1 1 d . . .
H17 H 0.332856 0.869383 0.545146 0.091 Uiso 1 1 calc R U .
C18 C 0.3259(4) 0.750000 0.5420(11) 0.064(3) Uani 1 2 d S T P
C19 C 0.2197(4) 0.750000 0.6260(11) 0.054(3) Uani 1 2 d S T P
C20 C 0.2385(5) 0.750000 0.7685(12) 0.070(3) Uani 1 2 d S T P
H20 H 0.281649 0.750000 0.791762 0.084 Uiso 1 2 calc R U P
C21 C 0.1943(4) 0.750000 0.8759(11) 0.049(3) Uani 1 2 d S T P
H21 H 0.206763 0.750000 0.973267 0.059 Uiso 1 2 calc R U P
C22 C 0.1344(5) 0.750000 0.8412(13) 0.068(3) Uani 1 2 d S T P
H22 H 0.103816 0.750000 0.914756 0.082 Uiso 1 2 calc R U P
C23 C 0.1156(5) 0.750000 0.7012(16) 0.105(5) Uani 1 2 d S T P
H23 H 0.072313 0.750000 0.679035 0.126 Uiso 1 2 calc R U P
C24 C 0.1590(4) 0.750000 0.5920(12) 0.059(3) Uani 1 2 d S T P
H24 H 0.146062 0.750000 0.494949 0.071 Uiso 1 2 calc R U P
N1 N 0.4181(3) 0.6871(3) 0.1118(6) 0.0500(15) Uani 1 1 d . . .
O1 O 0.2609(3) 0.750000 0.5146(8) 0.126(4) Uani 1 2 d S T P
Ni1 Ni 0.39929(5) 0.750000 0.39550(12) 0.0344(4) Uani 1 2 d S T P
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'
N N 0.0061 0.0033 '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'
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
N1 C1 N1 104.0(8) 7_575 .
N1 C1 Ni1 128.0(4) 7_575 .
N1 C1 Ni1 128.0(4) . .
N1 C2 C2 102.4(3) . 7_575
N1 C2 H2A 111.3 . .
C2 C2 H2A 111.3 7_575 .
N1 C2 H2B 111.3 . .
C2 C2 H2B 111.3 7_575 .
H2A C2 H2B 109.2 . .
C4 C3 C8 123.3(8) . .
C4 C3 N1 118.9(7) . .
C8 C3 N1 117.8(9) . .
C3 C4 C5 118.1(9) . .
C3 C4 C9 121.8(7) . .
C5 C4 C9 120.0(10) . .
C4 C5 C6 118.8(12) . .
C4 C5 H5 120.6 . .
C6 C5 H5 120.6 . .
C7 C6 C5 121.0(13) . .
C7 C6 H6 119.5 . .
C5 C6 H6 119.5 . .
C6 C7 C8 123.8(14) . .
C6 C7 H7 118.1 . .
C8 C7 H7 118.1 . .
C7 C8 C3 114.9(12) . .
C7 C8 C12 122.0(10) . .
C3 C8 C12 123.1(8) . .
C11 C9 C10 114.8(11) . .
C11 C9 C4 111.7(7) . .
C10 C9 C4 112.2(8) . .
C11 C9 H9 105.8 . .
C10 C9 H9 105.8 . .
C4 C9 H9 105.8 . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C9 C11 H11A 109.5 . .
C9 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C9 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C13 C12 C8 113.5(9) . .
C13 C12 C14 109.1(8) . .
C8 C12 C14 112.1(10) . .
C13 C12 H12 107.3 . .
C8 C12 H12 107.3 . .
C14 C12 H12 107.3 . .
C12 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C12 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C12 C14 H14A 109.5 . .
C12 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C12 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C16 C15 C16 119.4(11) . 7_575
C16 C15 Ni1 70.6(5) . .
C16 C15 Ni1 70.6(5) 7_575 .
C16 C15 H15 120.3 . .
C16 C15 H15 120.3 7_575 .
Ni1 C15 H15 131.1 . .
C17 C16 C15 120.0(9) . .
C17 C16 Ni1 71.2(5) . .
C15 C16 Ni1 70.5(6) . .
C17 C16 H16 120.0 . .
C15 C16 H16 120.0 . .
Ni1 C16 H16 131.0 . .
C18 C17 C16 118.2(9) . .
C18 C17 Ni1 69.5(5) . .
C16 C17 Ni1 70.9(5) . .
C18 C17 H17 120.9 . .
C16 C17 H17 120.9 . .
Ni1 C17 H17 131.3 . .
C17 C18 C17 124.1(11) 7_575 .
C17 C18 O1 118.0(5) 7_575 .
C17 C18 O1 118.0(5) . .
C17 C18 Ni1 72.5(5) 7_575 .
C17 C18 Ni1 72.5(5) . .
O1 C18 Ni1 128.5(7) . .
C24 C19 O1 116.5(9) . .
C24 C19 C20 120.5(10) . .
O1 C19 C20 123.0(9) . .
C21 C20 C19 120.0(10) . .
C21 C20 H20 120.0 . .
C19 C20 H20 120.0 . .
C22 C21 C20 119.1(11) . .
C22 C21 H21 120.4 . .
C20 C21 H21 120.4 . .
C21 C22 C23 121.2(11) . .
C21 C22 H22 119.4 . .
C23 C22 H22 119.4 . .
C22 C23 C24 120.6(11) . .
C22 C23 H23 119.7 . .
C24 C23 H23 119.7 . .
C19 C24 C23 118.6(11) . .
C19 C24 H24 120.7 . .
C23 C24 H24 120.7 . .
C1 N1 C3 121.5(5) . .
C1 N1 C2 115.6(5) . .
C3 N1 C2 122.8(5) . .
C19 O1 C18 119.8(8) . .
C1 Ni1 C18 139.6(4) . .
C1 Ni1 C15 139.4(4) . .
C18 Ni1 C15 81.0(4) . .
C1 Ni1 C16 139.1(3) . .
C18 Ni1 C16 68.2(3) . .
C15 Ni1 C16 38.8(3) . .
C1 Ni1 C16 139.1(3) . 7_575
C18 Ni1 C16 68.2(3) . 7_575
C15 Ni1 C16 38.8(3) . 7_575
C16 Ni1 C16 70.1(5) . 7_575
C1 Ni1 C17 138.7(3) . 7_575
C18 Ni1 C17 38.0(3) . 7_575
C15 Ni1 C17 69.3(3) . 7_575
C16 Ni1 C17 82.2(3) . 7_575
C16 Ni1 C17 37.8(3) 7_575 7_575
C1 Ni1 C17 138.7(3) . .
C18 Ni1 C17 38.0(3) . .
C15 Ni1 C17 69.3(3) . .
C16 Ni1 C17 37.8(3) . .
C16 Ni1 C17 82.2(3) 7_575 .
C17 Ni1 C17 69.5(5) 7_575 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.354(7) 7_575
C1 N1 1.354(7) .
C1 Ni1 1.853(9) .
C2 N1 1.466(8) .
C2 C2 1.505(13) 7_575
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C4 1.391(12) .
C3 C8 1.416(11) .
C3 N1 1.437(9) .
C4 C5 1.401(11) .
C4 C9 1.521(12) .
C5 C6 1.409(19) .
C5 H5 0.9500 .
C6 C7 1.32(2) .
C6 H6 0.9500 .
C7 C8 1.396(16) .
C7 H7 0.9500 .
C8 C12 1.512(14) .
C9 C11 1.473(11) .
C9 C10 1.479(12) .
C9 H9 1.0000 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 C13 1.508(12) .
C12 C14 1.534(12) .
C12 H12 1.0000 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 C16 1.411(11) .
C15 C16 1.411(11) 7_575
C15 Ni1 2.121(11) .
C15 H15 0.9500 .
C16 C17 1.378(12) .
C16 Ni1 2.122(8) .
C16 H16 0.9500 .
C17 C18 1.372(10) .
C17 Ni1 2.126(8) .
C17 H17 0.9500 .
C18 O1 1.415(12) .
C18 Ni1 2.087(10) .
C19 C24 1.340(13) .
C19 O1 1.367(11) .
C19 C20 1.394(14) .
C20 C21 1.381(13) .
C20 H20 0.9500 .
C21 C22 1.326(14) .
C21 H21 0.9500 .
C22 C23 1.371(17) .
C22 H22 0.9500 .
C23 C24 1.383(15) .
C23 H23 0.9500 .
C24 H24 0.9500 .
