#------------------------------------------------------------------------------
#$Date: 2016-03-25 14:26:50 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179896 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/92/7019229.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_7019229
loop_
_publ_author_name
'Li, Junye'
'Wang, Chenggen'
'Li, Xiaoyan'
'Sun, Hongjian'
_publ_section_title
;
 C-Cl bond activation of ortho-chlorinated benzamides by nickel and cobalt
 compounds supported with phosphine ligands.
;
_journal_issue                   28
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              8715
_journal_page_last               8722
_journal_paper_doi               10.1039/c2dt12395a
_journal_volume                  41
_journal_year                    2012
_chemical_formula_moiety         'C20 H30 Cl N Ni O P2'
_chemical_formula_sum            'C20 H30 Cl N Ni O P2'
_chemical_formula_weight         456.53
_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                 106.80(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.506(3)
_cell_length_b                   14.564(3)
_cell_length_c                   12.115(2)
_cell_measurement_temperature    423(2)
_cell_volume                     2281.3(9)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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      423(2)
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '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  0.0606
_diffrn_reflns_av_sigmaI/netI    0.0510
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10503
_diffrn_reflns_theta_full        26.70
_diffrn_reflns_theta_max         26.70
_diffrn_reflns_theta_min         1.57
_exptl_absorpt_coefficient_mu    1.117
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.728
_refine_diff_density_min         -1.110
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.825
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         4562
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.825
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.144
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1174
_reflns_number_gt                3752
_reflns_number_total             4832
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2dt12395a.txt
_cod_data_source_block           sun12a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        2281.3(8)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7019229
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
Ni1 Ni -0.279430(18) 0.357029(18) -0.15180(2) 0.02212(12) Uani 1 1 d .
P1 P -0.44408(4) 0.35874(4) -0.15934(6) 0.02924(17) Uani 1 1 d .
P2 P -0.11716(4) 0.35873(4) -0.15445(6) 0.02433(16) Uani 1 1 d .
Cl1 Cl -0.25208(5) 0.22761(4) -0.05238(6) 0.03922(18) Uani 1 1 d .
O1 O -0.26340(15) 0.67872(11) -0.09634(17) 0.0395(4) Uani 1 1 d .
N1 N -0.25536(15) 0.53553(13) -0.02109(18) 0.0270(4) Uani 1 1 d .
C1 C -0.4761(2) 0.3184(2) -0.0323(3) 0.0446(7) Uani 1 1 d .
H1A H -0.4423 0.3563 0.0324 0.067 Uiso 1 1 calc R
H1B H -0.4534 0.2560 -0.0167 0.067 Uiso 1 1 calc R
H1C H -0.5496 0.3215 -0.0455 0.067 Uiso 1 1 calc R
C2 C -0.5119(2) 0.2805(3) -0.2720(3) 0.0603(9) Uani 1 1 d .
H2A H -0.4855 0.2195 -0.2534 0.090 Uiso 1 1 calc R
H2B H -0.5018 0.2991 -0.3440 0.090 Uiso 1 1 calc R
H2C H -0.5844 0.2814 -0.2783 0.090 Uiso 1 1 calc R
C3 C -0.5180(2) 0.4640(2) -0.1952(3) 0.0559(9) Uani 1 1 d .
H3A H -0.5891 0.4520 -0.2005 0.084 Uiso 1 1 calc R
H3B H -0.5132 0.4868 -0.2678 0.084 Uiso 1 1 calc R
H3C H -0.4909 0.5089 -0.1362 0.084 Uiso 1 1 calc R
C4 C -0.07144(18) 0.45274(19) -0.2244(3) 0.0417(7) Uani 1 1 d .
H4A H 0.0012 0.4454 -0.2148 0.062 Uiso 1 1 calc R
H4B H -0.0831 0.5098 -0.1905 0.062 Uiso 1 1 calc R
H4C H -0.1082 0.4529 -0.3051 0.062 Uiso 1 1 calc R
C5 C -0.0843(2) 0.25950(19) -0.2264(3) 0.0420(7) Uani 1 1 d .
H5A H -0.1264 0.2586 -0.3052 0.063 Uiso 1 1 calc R
H5B H -0.0964 0.2047 -0.1882 0.063 Uiso 1 1 calc R
H5C H -0.0127 0.2626 -0.2239 0.063 Uiso 1 1 calc R
C6 C -0.02649(19) 0.3566(2) -0.0112(3) 0.0473(8) Uani 1 1 d .
H6A H -0.0368 0.3018 0.0280 0.071 Uiso 1 1 calc R
H6B H -0.0376 0.4094 0.0313 0.071 Uiso 1 1 calc R
H6C H 0.0429 0.3577 -0.0170 0.071 Uiso 1 1 calc R
C7 C -0.30558(15) 0.45883(15) -0.2535(2) 0.0239(5) Uani 1 1 d .
C8 C -0.33226(17) 0.43249(18) -0.3699(2) 0.0306(5) Uani 1 1 d .
C9 C -0.35233(19) 0.4960(2) -0.4586(3) 0.0392(6) Uani 1 1 d .
C10 C -0.3461(2) 0.5891(2) -0.4336(2) 0.0414(6) Uani 1 1 d .
C11 C -0.31983(18) 0.61742(18) -0.3201(2) 0.0326(5) Uani 1 1 d .
C12 C -0.29981(15) 0.55365(15) -0.2294(2) 0.0256(5) Uani 1 1 d .
C13 C -0.27154(15) 0.59559(15) -0.1108(2) 0.0247(5) Uani 1 1 d .
C14 C -0.22661(15) 0.55410(14) 0.0988(2) 0.0239(4) Uani 1 1 d .
C15 C -0.20974(17) 0.64166(15) 0.1457(2) 0.0269(5) Uani 1 1 d .
C16 C -0.17789(17) 0.65278(16) 0.2646(2) 0.0297(5) Uani 1 1 d .
C17 C -0.16165(16) 0.57819(17) 0.3393(2) 0.0294(5) Uani 1 1 d .
C18 C -0.18224(17) 0.49086(17) 0.2910(2) 0.0298(5) Uani 1 1 d .
C19 C -0.21372(16) 0.47846(16) 0.1725(2) 0.0267(5) Uani 1 1 d .
C20 C -0.1204(2) 0.5923(2) 0.4677(2) 0.0436(6) Uani 1 1 d .
H20A H -0.1371 0.5399 0.5069 0.065 Uiso 1 1 calc R
H20B H -0.1511 0.6462 0.4893 0.065 Uiso 1 1 calc R
H20C H -0.0467 0.5997 0.4885 0.065 Uiso 1 1 calc R
H19 H -0.2267(19) 0.420(2) 0.141(2) 0.030(7) Uiso 1 1 d .
H11 H -0.312(2) 0.677(2) -0.300(3) 0.044(8) Uiso 1 1 d .
H16 H -0.167(2) 0.7121(18) 0.298(2) 0.029(6) Uiso 1 1 d .
H10 H -0.360(3) 0.632(2) -0.495(3) 0.055(10) Uiso 1 1 d .
H18 H -0.175(2) 0.4387(18) 0.339(2) 0.029(7) Uiso 1 1 d .
H8 H -0.334(2) 0.3716(19) -0.388(3) 0.032(7) Uiso 1 1 d .
H15 H -0.217(2) 0.690(2) 0.103(3) 0.033(7) Uiso 1 1 d .
H1 H -0.269(2) 0.479(2) -0.042(3) 0.038(8) Uiso 1 1 d .
H9 H -0.367(2) 0.476(2) -0.535(3) 0.047(9) Uiso 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'
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'
P P 0.1023 0.0942 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 Ni1 P1 88.17(7)
C7 Ni1 P2 88.91(7)
P1 Ni1 P2 176.66(3)
C7 Ni1 Cl1 172.91(7)
P1 Ni1 Cl1 92.29(3)
P2 Ni1 Cl1 90.42(3)
C3 P1 C1 103.13(16)
C3 P1 C2 103.17(18)
C1 P1 C2 104.05(16)
C3 P1 Ni1 120.01(10)
C1 P1 Ni1 116.61(9)
C2 P1 Ni1 108.04(11)
C5 P2 C6 104.85(15)
C5 P2 C4 102.39(15)
C6 P2 C4 103.51(14)
C5 P2 Ni1 112.46(9)
C6 P2 Ni1 112.70(10)
C4 P2 Ni1 119.42(8)
C13 N1 C14 128.93(19)
C8 C7 C12 117.3(2)
C8 C7 Ni1 112.63(17)
C12 C7 Ni1 130.03(18)
C9 C8 C7 122.2(2)
C10 C9 C8 119.8(3)
C9 C10 C11 119.5(3)
C10 C11 C12 121.2(2)
C11 C12 C7 120.0(2)
C11 C12 C13 114.6(2)
C7 C12 C13 125.4(2)
O1 C13 N1 122.2(2)
O1 C13 C12 121.7(2)
N1 C13 C12 116.04(19)
C19 C14 C15 119.2(2)
C19 C14 N1 116.8(2)
C15 C14 N1 124.0(2)
C14 C15 C16 119.8(2)
C17 C16 C15 121.8(2)
C16 C17 C18 117.7(2)
C16 C17 C20 120.5(2)
C18 C17 C20 121.8(2)
C19 C18 C17 121.2(2)
C18 C19 C14 120.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ni1 C7 1.895(2)
Ni1 P1 2.1992(8)
Ni1 P2 2.2012(7)
Ni1 Cl1 2.2096(7)
P1 C3 1.812(3)
P1 C1 1.812(3)
P1 C2 1.811(3)
P2 C5 1.808(3)
P2 C6 1.812(3)
P2 C4 1.810(3)
O1 C13 1.224(3)
N1 C13 1.363(3)
N1 C14 1.417(3)
C7 C8 1.403(3)
C7 C12 1.409(3)
C8 C9 1.385(4)
C9 C10 1.386(4)
C10 C11 1.379(4)
C11 C12 1.404(3)
C12 C13 1.505(3)
C14 C19 1.397(3)
C14 C15 1.388(3)
C15 C16 1.389(4)
C16 C17 1.390(4)
C17 C18 1.394(4)
C17 C20 1.507(4)
C18 C19 1.386(4)
