#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/30/43/4304350.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_4304350
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         'C30 H31 Br Cl2 N P'
_chemical_formula_sum            'C30 H31 Br Cl2 N P'
_chemical_formula_weight         587.34
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 122.569(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.3127(4)
_cell_length_b                   10.0835(3)
_cell_length_c                   16.2680(3)
_cell_measurement_reflns_used    7850
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.037
_cell_volume                     2946.32(13)
_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-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0375
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9073
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    1.650
_exptl_absorpt_correction_T_max  0.6905
_exptl_absorpt_correction_T_min  0.5918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 ?
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.005(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    fixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4345
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0380
_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)+(0.0588P)²+3.8036P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1219
_reflns_number_gt                3986
_reflns_number_total             4345
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic701836j-file003_2.cif
_cod_data_source_block           2836
_cod_original_cell_volume        2946.32(12)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4304350
loop_
_symmetry_equiv_pos_as_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'
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
C1 C 0.1157(3) 0.7540(5) -0.3387(3) 0.0396(11) Uani 1 1 d . . .
C2 C 0.0963(3) 0.6190(6) -0.3187(4) 0.0544(14) Uani 1 1 d . . .
H2A H 0.0539 0.6263 -0.3130 0.082 Uiso 1 1 calc R . .
H2B H 0.1379 0.5847 -0.2589 0.082 Uiso 1 1 calc R . .
H2C H 0.0849 0.5601 -0.3713 0.082 Uiso 1 1 calc R . .
C3 C 0.1732(3) 0.7774(5) -0.3503(4) 0.0419(11) Uani 1 1 d . . .
H3 H 0.1775 0.8623 -0.3691 0.050 Uiso 1 1 calc R . .
C4 C 0.2030(3) 0.5313(5) -0.4238(3) 0.0430(11) Uani 1 1 d . . .
C5 C 0.2462(3) 0.4213(6) -0.4139(4) 0.0572(14) Uani 1 1 d . . .
H5 H 0.2944 0.4131 -0.3596 0.069 Uiso 1 1 calc R . .
C6 C 0.2168(4) 0.3239(6) -0.4857(5) 0.0717(18) Uani 1 1 d . . .
H6 H 0.2452 0.2493 -0.4781 0.086 Uiso 1 1 calc R . .
C7 C 0.1468(4) 0.3363(7) -0.5673(5) 0.0713(18) Uani 1 1 d . . .
H7 H 0.1277 0.2709 -0.6152 0.086 Uiso 1 1 calc R . .
C8 C 0.1054(3) 0.4449(7) -0.5779(4) 0.0668(17) Uani 1 1 d . . .
H8 H 0.0581 0.4540 -0.6338 0.080 Uiso 1 1 calc R . .
C9 C 0.1324(3) 0.5422(6) -0.5069(4) 0.0504(12) Uani 1 1 d . . .
H9 H 0.1030 0.6153 -0.5151 0.060 Uiso 1 1 calc R . .
C10 C 0.2840(3) 0.5884(5) -0.2125(3) 0.0453(11) Uani 1 1 d . . .
C11 C 0.2810(4) 0.4557(6) -0.1939(5) 0.0688(17) Uani 1 1 d . . .
H11 H 0.2560 0.3955 -0.2449 0.083 Uiso 1 1 calc R . .
C12 C 0.3160(5) 0.4136(9) -0.0974(6) 0.094(2) Uani 1 1 d . . .
H12 H 0.3151 0.3244 -0.0834 0.113 Uiso 1 1 calc R . .
C13 C 0.3523(4) 0.5051(9) -0.0220(5) 0.087(2) Uani 1 1 d . . .
H13 H 0.3764 0.4757 0.0422 0.104 Uiso 1 1 calc R . .
C14 C 0.3533(5) 0.6381(9) -0.0400(5) 0.077(2) Uani 1 1 d . . .
H14 H 0.3770 0.6986 0.0111 0.092 Uiso 1 1 calc R . .
C15 C 0.3183(4) 0.6797(7) -0.1358(5) 0.0602(16) Uani 1 1 d . . .
H15 H 0.3176 0.7695 -0.1495 0.072 Uiso 1 1 calc R . .
C16 C 0.3102(3) 0.7449(5) -0.3415(3) 0.0438(11) Uani 1 1 d . . .
C17 C 0.3818(3) 0.6939(7) -0.2936(4) 0.0644(16) Uani 1 1 d . . .
H17 H 0.3932 0.6188 -0.2547 0.077 Uiso 1 1 calc R . .
C18 C 0.4362(4) 0.7523(10) -0.3024(5) 0.085(2) Uani 1 1 d . . .
H18 H 0.4841 0.7170 -0.2695 0.102 Uiso 1 1 calc R . .
C19 C 0.4200(5) 0.8615(9) -0.3592(7) 0.093(2) Uani 1 1 d . . .
H19 H 0.4568 0.9019 -0.3647 0.112 Uiso 1 1 calc R . .
C20 C 0.3488(5) 0.9124(9) -0.4085(8) 0.108(3) Uani 1 1 d . . .
H20 H 0.3384 0.9873 -0.4473 0.130 Uiso 1 1 calc R . .
C21 C 0.2926(4) 0.8559(7) -0.4024(6) 0.079(2) Uani 1 1 d . . .
H21 H 0.2445 0.8902 -0.4375 0.095 Uiso 1 1 calc R . .
C22 C 0.0782(3) 0.9873(5) -0.3616(4) 0.0432(11) Uani 1 1 d . . .
C23 C 0.0529(3) 1.0284(5) -0.4574(4) 0.0504(13) Uani 1 1 d . . .
C24 C 0.0234(4) 0.9302(7) -0.5402(4) 0.0710(17) Uani 1 1 d . . .
H24A H 0.0094 0.9762 -0.5994 0.106 Uiso 1 1 calc R . .
H24B H -0.0193 0.8857 -0.5479 0.106 Uiso 1 1 calc R . .
H24C H 0.0613 0.8662 -0.5260 0.106 Uiso 1 1 calc R . .
C25 C 0.0578(4) 1.1612(6) -0.4730(5) 0.0618(16) Uani 1 1 d . . .
H25 H 0.0420 1.1904 -0.5355 0.074 Uiso 1 1 calc R . .
C26 C 0.0851(4) 1.2497(7) -0.3995(6) 0.0706(18) Uani 1 1 d . . .
H26 H 0.0874 1.3389 -0.4120 0.085 Uiso 1 1 calc R . .
C27 C 0.1098(4) 1.2093(6) -0.3057(5) 0.0674(17) Uani 1 1 d . . .
H27 H 0.1286 1.2716 -0.2557 0.081 Uiso 1 1 calc R . .
C28 C 0.1067(3) 1.0756(5) -0.2851(4) 0.0511(13) Uani 1 1 d . . .
C29 C 0.1346(4) 1.0290(7) -0.1831(5) 0.0779(19) Uani 1 1 d . . .
H29A H 0.1524 1.1035 -0.1395 0.117 Uiso 1 1 calc R . .
H29B H 0.1745 0.9668 -0.1628 0.117 Uiso 1 1 calc R . .
H29C H 0.0948 0.9868 -0.1818 0.117 Uiso 1 1 calc R . .
C30 C 0.3887(6) 1.0821(13) -0.1621(10) 0.156(5) Uani 1 1 d . . .
H30A H 0.4001 1.0594 -0.2107 0.188 Uiso 1 1 calc R . .
H30B H 0.4078 1.1707 -0.1390 0.188 Uiso 1 1 calc R . .
Br1 Br 0.45269(3) 0.69713(6) 0.22825(3) 0.0640(2) Uani 1 1 d . . .
Cl1 Cl 0.29234(13) 1.0873(3) -0.2196(2) 0.1233(10) Uani 1 1 d . . .
Cl2 Cl 0.43455(14) 0.9788(3) -0.0695(2) 0.1313(10) Uani 1 1 d . . .
N1 N 0.0709(2) 0.8507(4) -0.3436(3) 0.0443(9) Uani 1 1 d . . .
H1 H 0.0354 0.8297 -0.3354 0.053 Uiso 1 1 calc R . .
P1 P 0.23957(7) 0.66044(12) -0.33272(8) 0.0385(3) Uani 1 1 d . . .
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'
Br Br -0.2901 2.4595 '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'
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
N1 C1 C3 122.3(5) . . ?
N1 C1 C2 113.7(4) . . ?
C3 C1 C2 124.0(5) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 P1 125.0(4) . . ?
C1 C3 H3 117.5 . . ?
P1 C3 H3 117.5 . . ?
C9 C4 C5 118.6(5) . . ?
C9 C4 P1 120.5(4) . . ?
C5 C4 P1 120.8(4) . . ?
C6 C5 C4 119.6(6) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C7 C6 C5 120.9(6) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C8 C7 C6 119.4(6) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 121.1(6) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C8 C9 C4 120.4(5) . . ?
C8 C9 H9 119.8 . . ?
C4 C9 H9 119.8 . . ?
C11 C10 C15 120.5(5) . . ?
C11 C10 P1 124.6(4) . . ?
C15 C10 P1 114.7(4) . . ?
C10 C11 C12 118.8(7) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C11 C12 C13 119.9(7) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 121.6(6) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C15 C14 C13 118.4(7) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
C14 C15 C10 120.8(6) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C17 C16 C21 119.2(5) . . ?
C17 C16 P1 119.6(4) . . ?
C21 C16 P1 121.0(4) . . ?
C18 C17 C16 121.2(6) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C19 C18 C17 119.9(7) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 119.8(7) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C21 C20 C19 122.1(7) . . ?
C21 C20 H20 118.9 . . ?
C19 C20 H20 118.9 . . ?
C20 C21 C16 117.9(7) . . ?
C20 C21 H21 121.1 . . ?
C16 C21 H21 121.1 . . ?
C28 C22 C23 122.0(5) . . ?
C28 C22 N1 118.7(4) . . ?
C23 C22 N1 119.3(5) . . ?
C25 C23 C22 117.9(5) . . ?
C25 C23 C24 120.7(5) . . ?
C22 C23 C24 121.5(5) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C23 121.3(6) . . ?
C26 C25 H25 119.3 . . ?
C23 C25 H25 119.3 . . ?
C25 C26 C27 120.7(6) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 H26 119.6 . . ?
C26 C27 C28 120.6(6) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
C22 C28 C27 117.5(5) . . ?
C22 C28 C29 121.0(5) . . ?
C27 C28 C29 121.5(5) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
Cl2 C30 Cl1 117.2(6) . . ?
Cl2 C30 H30A 108.0 . . ?
Cl1 C30 H30A 108.0 . . ?
Cl2 C30 H30B 108.0 . . ?
Cl1 C30 H30B 108.0 . . ?
H30A C30 H30B 107.2 . . ?
C1 N1 C22 124.0(4) . . ?
C1 N1 H1 118.0 . . ?
C22 N1 H1 118.0 . . ?
C3 P1 C16 107.8(2) . . ?
C3 P1 C10 110.9(2) . . ?
C16 P1 C10 107.6(2) . . ?
C3 P1 C4 113.6(2) . . ?
C16 P1 C4 106.7(2) . . ?
C10 P1 C4 110.0(2) . . ?
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
C1 N1 1.338(7) . ?
C1 C3 1.358(7) . ?
C1 C2 1.507(8) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 P1 1.743(5) . ?
C3 H3 0.9300 . ?
C4 C9 1.383(7) . ?
C4 C5 1.395(8) . ?
C4 P1 1.803(5) . ?
C5 C6 1.391(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.369(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.359(10) . ?
C7 H7 0.9300 . ?
C8 C9 1.382(8) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.381(8) . ?
C10 C15 1.399(8) . ?
C10 P1 1.805(5) . ?
C11 C12 1.393(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.390(11) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(11) . ?
C13 H13 0.9300 . ?
C14 C15 1.382(9) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.386(8) . ?
C16 C21 1.405(8) . ?
C16 P1 1.800(5) . ?
C17 C18 1.377(10) . ?
C17 H17 0.9300 . ?
C18 C19 1.357(12) . ?
C18 H18 0.9300 . ?
C19 C20 1.377(12) . ?
C19 H19 0.9300 . ?
C20 C21 1.380(10) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C28 1.376(7) . ?
C22 C23 1.410(7) . ?
C22 N1 1.434(7) . ?
C23 C25 1.378(8) . ?
C23 C24 1.509(8) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.347(10) . ?
C25 H25 0.9300 . ?
C26 C27 1.381(10) . ?
C26 H26 0.9300 . ?
C27 C28 1.399(9) . ?
C27 H27 0.9300 . ?
C28 C29 1.506(9) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 Cl2 1.651(11) . ?
C30 Cl1 1.740(10) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
N1 H1 0.8600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21196835
