#------------------------------------------------------------------------------
#$Date: 2016-03-22 23:52:03 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179081 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/43/4304352.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_4304352
loop_
_publ_author_name
'Pei-Ying Lee'
'Lan-Chang Liang'
_publ_section_title
;
Nickel(II) Complexes Containing Bidentate Amido Phosphine Ligands Derived
from α-Iminophosphorus Ylides: Synthesis and Structural Characterization
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              749
_journal_page_last               758
_journal_paper_doi               10.1021/ic701836j
_journal_volume                  47
_journal_year                    2008
_chemical_formula_moiety         'C33 H36 N P'
_chemical_formula_sum            'C33 H36 N P'
_chemical_formula_weight         477.60
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 97.413(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7040(6)
_cell_length_b                   15.4800(11)
_cell_length_c                   18.6280(14)
_cell_measurement_reflns_used    62227
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.037
_cell_volume                     2774.9(3)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 19'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_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  0.0682
_diffrn_reflns_av_sigmaI/netI    0.0824
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13546
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  1.0454
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 ?
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.143
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.212
_refine_ls_extinction_coef       0.041(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    fixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4849
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1281
_refine_ls_R_factor_gt           0.0682
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1026P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1523
_refine_ls_wR_factor_ref         0.1875
_reflns_number_gt                2770
_reflns_number_total             4849
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic701836j-file003_4.cif
_cod_data_source_block           2863
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4304352
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.47074(7) 0.18493(5) 0.28678(4) 0.0479(3) Uani 1 1 d . . .
N1 N 0.6741(2) 0.17668(15) 0.17763(12) 0.0513(6) Uani 1 1 d . . .
C1 C 0.5671(3) 0.27948(19) 0.32331(16) 0.0498(7) Uani 1 1 d . . .
C2 C 0.6557(3) 0.2789(2) 0.38772(18) 0.0619(9) Uani 1 1 d . . .
H2 H 0.6718 0.2252 0.4132 0.074 Uiso 1 1 d R . .
C3 C 0.7206(4) 0.3543(3) 0.4139(2) 0.0761(10) Uani 1 1 d . . .
H3 H 0.7840 0.3543 0.4579 0.091 Uiso 1 1 d R . .
C4 C 0.6971(4) 0.4303(3) 0.3764(2) 0.0813(11) Uani 1 1 d . . .
H4 H 0.7400 0.4828 0.3956 0.098 Uiso 1 1 d R . .
C5 C 0.6086(4) 0.4317(2) 0.3128(2) 0.0786(11) Uani 1 1 d . . .
H5 H 0.5918 0.4850 0.2869 0.094 Uiso 1 1 d R . .
C6 C 0.5440(3) 0.3565(2) 0.28578(18) 0.0639(9) Uani 1 1 d . . .
H6 H 0.4840 0.3568 0.2405 0.077 Uiso 1 1 d R . .
C7 C 0.3055(3) 0.18880(18) 0.32165(16) 0.0489(7) Uani 1 1 d . . .
C8 C 0.1841(3) 0.1626(3) 0.28090(19) 0.0801(11) Uani 1 1 d . . .
H8 H 0.1884 0.1438 0.2322 0.096 Uiso 1 1 d R . .
C9 C 0.0596(4) 0.1660(3) 0.3097(2) 0.0993(14) Uani 1 1 d . . .
H9 H -0.0247 0.1481 0.2810 0.119 Uiso 1 1 d R . .
C10 C 0.0570(4) 0.1923(3) 0.3794(3) 0.0919(13) Uani 1 1 d . . .
H10 H -0.0310 0.1949 0.3977 0.110 Uiso 1 1 d R . .
C11 C 0.1766(4) 0.2157(2) 0.4209(2) 0.0818(11) Uani 1 1 d . . .
H11 H 0.1729 0.2342 0.4698 0.098 Uiso 1 1 d R . .
C12 C 0.3002(3) 0.2148(2) 0.39189(18) 0.0671(9) Uani 1 1 d . . .
H12 H 0.3867 0.2289 0.4205 0.081 Uiso 1 1 d R . .
C13 C 0.5613(3) 0.09351(19) 0.33207(16) 0.0534(8) Uani 1 1 d . . .
C14 C 0.7031(3) 0.0807(2) 0.32941(18) 0.0697(10) Uani 1 1 d . . .
H14 H 0.7525 0.1213 0.3033 0.084 Uiso 1 1 d R . .
C15 C 0.7713(4) 0.0116(3) 0.3639(2) 0.0849(11) Uani 1 1 d . . .
H15 H 0.8689 0.0037 0.3622 0.102 Uiso 1 1 d R . .
C16 C 0.7033(5) -0.0462(3) 0.4016(2) 0.0890(12) Uani 1 1 d . . .
H16 H 0.7533 -0.0946 0.4241 0.107 Uiso 1 1 d R . .
C17 C 0.5629(4) -0.0356(3) 0.4040(2) 0.0931(13) Uani 1 1 d . . .
H17 H 0.5157 -0.0753 0.4320 0.112 Uiso 1 1 d R . .
C18 C 0.4933(4) 0.0338(2) 0.3695(2) 0.0765(10) Uani 1 1 d . . .
H18 H 0.3954 0.0406 0.3710 0.092 Uiso 1 1 d R . .
C19 C 0.4381(3) 0.18357(19) 0.19514(15) 0.0516(8) Uani 1 1 d . . .
H19 H 0.3437 0.1857 0.1723 0.062 Uiso 1 1 d R . .
C20 C 0.5443(3) 0.18191(18) 0.14988(15) 0.0487(7) Uani 1 1 d . . .
C21 C 0.4988(3) 0.1867(2) 0.06982(16) 0.0700(10) Uani 1 1 d . . .
H21A H 0.3993 0.1901 0.0608 0.084 Uiso 1 1 d R . .
H21B H 0.5298 0.1357 0.0473 0.084 Uiso 1 1 d R . .
H21C H 0.5386 0.2368 0.0501 0.084 Uiso 1 1 d R . .
C22 C 0.7833(3) 0.1681(2) 0.13569(15) 0.0518(8) Uani 1 1 d . . .
C23 C 0.8305(3) 0.0849(2) 0.11953(16) 0.0562(8) Uani 1 1 d . . .
C24 C 0.7517(4) 0.0040(2) 0.13711(18) 0.0659(9) Uani 1 1 d . . .
H24 H 0.6836 0.0225 0.1668 0.079 Uiso 1 1 d R . .
C25 C 0.8439(4) -0.0596(3) 0.1822(2) 0.1013(13) Uani 1 1 d . . .
H25A H 0.7912 -0.1094 0.1930 0.122 Uiso 1 1 d R . .
H25B H 0.8828 -0.0324 0.2266 0.122 Uiso 1 1 d R . .
H25C H 0.9174 -0.0771 0.1555 0.122 Uiso 1 1 d R . .
C26 C 0.6795(4) -0.0389(3) 0.0693(2) 0.0873(11) Uani 1 1 d . . .
H26A H 0.6293 -0.0890 0.0817 0.105 Uiso 1 1 d R . .
H26B H 0.7475 -0.0557 0.0388 0.105 Uiso 1 1 d R . .
H26C H 0.6161 0.0017 0.0440 0.105 Uiso 1 1 d R . .
C27 C 0.9509(3) 0.0772(2) 0.08679(18) 0.0703(10) Uani 1 1 d . . .
H27 H 0.9850 0.0210 0.0763 0.084 Uiso 1 1 d R . .
C28 C 1.0233(4) 0.1488(3) 0.0696(2) 0.0758(10) Uani 1 1 d . . .
H28 H 1.1075 0.1418 0.0482 0.091 Uiso 1 1 d R . .
C29 C 0.9741(3) 0.2291(2) 0.0826(2) 0.0743(10) Uani 1 1 d . . .
H29 H 1.0241 0.2791 0.0698 0.089 Uiso 1 1 d R . .
C30 C 0.8544(3) 0.2415(2) 0.11445(17) 0.0599(9) Uani 1 1 d . . .
C31 C 0.8039(4) 0.3324(2) 0.1289(2) 0.0710(10) Uani 1 1 d . . .
H31 H 0.7085 0.3264 0.1367 0.085 Uiso 1 1 d R . .
C32 C 0.8135(5) 0.3952(3) 0.0667(3) 0.1102(15) Uani 1 1 d . . .
H32A H 0.7806 0.4511 0.0790 0.132 Uiso 1 1 d R . .
H32B H 0.7576 0.3742 0.0240 0.132 Uiso 1 1 d R . .
H32C H 0.9085 0.3997 0.0577 0.132 Uiso 1 1 d R . .
C33 C 0.8790(5) 0.3657(3) 0.1974(3) 0.1198(16) Uani 1 1 d . . .
H33A H 0.8473 0.4229 0.2068 0.144 Uiso 1 1 d R . .
H33B H 0.9767 0.3672 0.1936 0.144 Uiso 1 1 d R . .
H33C H 0.8624 0.3281 0.2364 0.144 Uiso 1 1 d R . .
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'
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
_geom_angle_publ_flag
C19 P1 C7 107.65(14) . . ?
C19 P1 C13 118.33(14) . . ?
C7 P1 C13 104.92(13) . . ?
C19 P1 C1 113.98(14) . . ?
C7 P1 C1 106.00(13) . . ?
C13 P1 C1 104.98(14) . . ?
C20 N1 C22 123.2(2) . . ?
C2 C1 C6 119.1(3) . . ?
C2 C1 P1 123.4(2) . . ?
C6 C1 P1 117.5(2) . . ?
C1 C2 C3 120.2(3) . . ?
C1 C2 H2 118.6 . . ?
C3 C2 H2 121.2 . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3 118.8 . . ?
C2 C3 H3 120.8 . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 120.2(3) . . ?
C1 C6 H6 119.2 . . ?
C5 C6 H6 120.6 . . ?
C12 C7 C8 118.4(3) . . ?
C12 C7 P1 119.7(2) . . ?
C8 C7 P1 121.9(2) . . ?
C7 C8 C9 120.2(3) . . ?
C7 C8 H8 118.2 . . ?
C9 C8 H8 121.6 . . ?
C10 C9 C8 120.3(4) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H10 121.4 . . ?
C9 C10 H10 118.5 . . ?
C10 C11 C12 119.9(4) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 121.0 . . ?
C7 C12 C11 121.1(3) . . ?
C7 C12 H12 117.2 . . ?
C11 C12 H12 121.6 . . ?
C18 C13 C14 117.5(3) . . ?
C18 C13 P1 121.6(2) . . ?
C14 C13 P1 120.9(2) . . ?
C15 C14 C13 120.7(3) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 118.9 . . ?
C16 C15 C14 121.2(4) . . ?
C16 C15 H15 118.7 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 119.0(4) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 121.7 . . ?
C16 C17 C18 120.2(4) . . ?
C16 C17 H17 118.9 . . ?
C18 C17 H17 120.7 . . ?
C13 C18 C17 121.3(3) . . ?
C13 C18 H18 118.8 . . ?
C17 C18 H18 119.9 . . ?
C20 C19 P1 123.0(2) . . ?
C20 C19 H19 117.7 . . ?
P1 C19 H19 119.3 . . ?
N1 C20 C19 120.5(3) . . ?
N1 C20 C21 122.9(3) . . ?
C19 C20 C21 116.6(3) . . ?
C20 C21 H21A 109.6 . . ?
C20 C21 H21B 109.0 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.8 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N1 C22 C23 119.7(3) . . ?
N1 C22 C30 120.8(3) . . ?
C23 C22 C30 119.3(3) . . ?
C27 C23 C22 119.0(3) . . ?
C27 C23 C24 119.8(3) . . ?
C22 C23 C24 121.1(3) . . ?
C25 C24 C26 110.8(3) . . ?
C25 C24 C23 112.2(3) . . ?
C26 C24 C23 111.8(3) . . ?
C25 C24 H24 106.1 . . ?
C26 C24 H24 109.4 . . ?
C23 C24 H24 106.3 . . ?
C24 C25 H25A 110.3 . . ?
C24 C25 H25B 109.4 . . ?
H25A C25 H25B 109.4 . . ?
C24 C25 H25C 108.8 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 110.3 . . ?
C24 C26 H26B 109.4 . . ?
H26A C26 H26B 109.4 . . ?
C24 C26 H26C 108.7 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.4 . . ?
C28 C27 C23 121.2(3) . . ?
C28 C27 H27 118.9 . . ?
C23 C27 H27 119.8 . . ?
C29 C28 C27 119.5(3) . . ?
C29 C28 H28 120.8 . . ?
C27 C28 H28 119.7 . . ?
C28 C29 C30 122.3(3) . . ?
C28 C29 H29 119.4 . . ?
C30 C29 H29 118.3 . . ?
C29 C30 C22 118.4(3) . . ?
C29 C30 C31 120.7(3) . . ?
C22 C30 C31 120.8(3) . . ?
C33 C31 C30 110.0(3) . . ?
C33 C31 C32 111.2(4) . . ?
C30 C31 C32 113.6(3) . . ?
C33 C31 H31 106.3 . . ?
C30 C31 H31 106.0 . . ?
C32 C31 H31 109.3 . . ?
C31 C32 H32A 109.8 . . ?
C31 C32 H32B 109.3 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.4 . . ?
H32A C32 H32C 109.4 . . ?
H32B C32 H32C 109.4 . . ?
C31 C33 H33A 110.2 . . ?
C31 C33 H33B 109.1 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.2 . . ?
H33A C33 H33C 109.4 . . ?
H33B C33 H33C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C19 1.696(3) . ?
P1 C7 1.807(3) . ?
P1 C13 1.815(3) . ?
P1 C1 1.821(3) . ?
N1 C20 1.301(4) . ?
N1 C22 1.402(3) . ?
C1 C2 1.383(4) . ?
C1 C6 1.386(4) . ?
C2 C3 1.386(5) . ?
C2 H2 0.9602 . ?
C3 C4 1.371(5) . ?
C3 H3 0.9592 . ?
C4 C5 1.370(5) . ?
C4 H4 0.9609 . ?
C5 C6 1.386(5) . ?
C5 H5 0.9591 . ?
C6 H6 0.9614 . ?
C7 C12 1.377(4) . ?
C7 C8 1.378(4) . ?
C8 C9 1.384(5) . ?
C8 H8 0.9588 . ?
C9 C10 1.364(6) . ?
C9 H9 0.9590 . ?
C10 C11 1.358(5) . ?
C10 H10 0.9603 . ?
C11 C12 1.377(4) . ?
C11 H11 0.9599 . ?
C12 H12 0.9595 . ?
C13 C18 1.376(4) . ?
C13 C14 1.398(4) . ?
C14 C15 1.373(5) . ?
C14 H14 0.9597 . ?
C15 C16 1.360(5) . ?
C15 H15 0.9595 . ?
C16 C17 1.378(5) . ?
C16 H16 0.9591 . ?
C17 C18 1.382(5) . ?
C17 H17 0.9598 . ?
C18 H18 0.9598 . ?
C19 C20 1.413(4) . ?
C19 H19 0.9593 . ?
C20 C21 1.501(4) . ?
C21 H21A 0.9599 . ?
C21 H21B 0.9602 . ?
C21 H21C 0.9601 . ?
C22 C23 1.413(4) . ?
C22 C30 1.413(4) . ?
C23 C27 1.390(4) . ?
C23 C24 1.524(4) . ?
C24 C25 1.511(5) . ?
C24 C26 1.517(5) . ?
C24 H24 0.9587 . ?
C25 H25A 0.9607 . ?
C25 H25B 0.9609 . ?
C25 H25C 0.9597 . ?
C26 H26A 0.9598 . ?
C26 H26B 0.9605 . ?
C26 H26C 0.9596 . ?
C27 C28 1.371(5) . ?
C27 H27 0.9599 . ?
C28 C29 1.365(5) . ?
C28 H28 0.9604 . ?
C29 C30 1.384(4) . ?
C29 H29 0.9598 . ?
C30 C31 1.525(4) . ?
C31 C33 1.477(5) . ?
C31 C32 1.525(5) . ?
C31 H31 0.9599 . ?
C32 H32A 0.9603 . ?
C32 H32B 0.9598 . ?
C32 H32C 0.9606 . ?
C33 H33A 0.9608 . ?
C33 H33B 0.9601 . ?
C33 H33C 0.9606 . ?
