#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/14/4501468.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_4501468
loop_
_publ_author_name
'Zhang, Liping'
'Hao, Xiang'
'Sun, Wen-Hua'
'Redshaw, Carl'
_publ_section_title
;
 Synthesis, Characterization, and Ethylene Polymerization Behavior of
 8-(Nitroarylamino)-5,6,7-trihydroquinolylnickel Dichlorides: Influence of
 the Nitro Group and Impurities on Catalytic Activity
;
_journal_issue                   10
_journal_name_full               'ACS Catalysis'
_journal_page_first              1213
_journal_paper_doi               10.1021/cs200308b
_journal_volume                  1
_journal_year                    2011
_chemical_formula_sum            'C20 H23 Cl3 N3 Ni0.5 O2'
_chemical_formula_weight         473.12
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                112.06(3)
_cell_angle_beta                 96.80(3)
_cell_angle_gamma                98.40(3)
_cell_formula_units_Z            2
_cell_length_a                   9.1269(18)
_cell_length_b                   10.212(2)
_cell_length_c                   12.557(3)
_cell_measurement_reflns_used    3079
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4819
_cell_measurement_theta_min      1.7820
_cell_volume                     1053.7(5)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_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  0.0491
_diffrn_reflns_av_sigmaI/netI    0.0566
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13000
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.78
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.890
_exptl_absorpt_correction_T_max  0.8781
_exptl_absorpt_correction_T_min  0.8421
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             490
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.654
_refine_diff_density_rms         0.156
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.300
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         4801
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.300
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0643
_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)+(0.0684P)²+0.4607P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1590
_refine_ls_wR_factor_ref         0.1703
_reflns_number_gt                4283
_reflns_number_total             4801
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs200308b_si_001.cif
_cod_data_source_block           Ni5
_cod_depositor_comments
;
The following automatic conversions were performed:

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

'_exptl_absorpt_correction_type' value 'Numerical'
changed to 'numerical' 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 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1053.7(4)
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C20 H23 Cl3 N3 Ni0.50 O2'
_cod_database_code               4501468
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.0000 0.0000 0.0000 0.01948(18) Uani 1 2 d S
Cl1 Cl 0.09526(9) -0.20321(9) -0.00114(7) 0.0256(2) Uani 1 1 d .
N1 N 0.2220(3) 0.1027(3) 0.0187(2) 0.0209(6) Uani 1 1 d .
N2 N 0.0308(3) -0.0501(3) -0.1859(2) 0.0208(6) Uani 1 1 d .
N3 N -0.4541(4) -0.2978(4) -0.5708(3) 0.0383(8) Uani 1 1 d .
O1 O -0.4918(4) -0.4306(4) -0.6182(3) 0.0616(10) Uani 1 1 d .
O2 O -0.5240(4) -0.2167(4) -0.5968(3) 0.0506(8) Uani 1 1 d .
C17 C 0.1011(5) -0.3792(5) -0.3326(4) 0.0456(11) Uani 1 1 d .
H17A H 0.1405 -0.4448 -0.3018 0.068 Uiso 1 1 calc R
H17B H 0.1695 -0.2843 -0.2974 0.068 Uiso 1 1 calc R
H17C H 0.0932 -0.4183 -0.4178 0.068 Uiso 1 1 calc R
C16 C -0.0552(4) -0.3638(4) -0.3028(4) 0.0328(9) Uani 1 1 d .
H16A H -0.1223 -0.4607 -0.3369 0.039 Uiso 1 1 calc R
H16B H -0.0462 -0.3268 -0.2168 0.039 Uiso 1 1 calc R
C14 C -0.2487(4) -0.3241(4) -0.4397(3) 0.0277(8) Uani 1 1 d .
H14A H -0.2818 -0.4260 -0.4781 0.033 Uiso 1 1 calc R
C15 C -0.1280(4) -0.2648(4) -0.3461(3) 0.0240(7) Uani 1 1 d .
C13 C -0.3205(4) -0.2344(4) -0.4766(3) 0.0292(8) Uani 1 1 d .
C18 C -0.0977(4) 0.1407(4) -0.2824(3) 0.0270(8) Uani 1 1 d .
H18A H -0.0028 0.1679 -0.2249 0.032 Uiso 1 1 calc R
H18B H -0.1744 0.1850 -0.2398 0.032 Uiso 1 1 calc R
C12 C -0.2719(4) -0.0855(4) -0.4266(3) 0.0283(8) Uani 1 1 d .
H12A H -0.3219 -0.0269 -0.4556 0.034 Uiso 1 1 calc R
C11 C -0.1496(4) -0.0222(4) -0.3337(3) 0.0232(7) Uani 1 1 d .
C10 C -0.0811(4) -0.1124(4) -0.2919(3) 0.0223(7) Uani 1 1 d .
C19 C -0.0711(5) 0.2032(5) -0.3735(4) 0.0391(10) Uani 1 1 d .
H19A H -0.0380 0.3084 -0.3343 0.059 Uiso 1 1 calc R
H19B H -0.1652 0.1791 -0.4298 0.059 Uiso 1 1 calc R
H19C H 0.0067 0.1621 -0.4148 0.059 Uiso 1 1 calc R
C8 C 0.2226(4) -0.0114(4) -0.3019(3) 0.0272(8) Uani 1 1 d .
H8A H 0.2182 0.0789 -0.3132 0.033 Uiso 1 1 calc R
H8B H 0.1563 -0.0924 -0.3698 0.033 Uiso 1 1 calc R
C9 C 0.1666(4) -0.0021(4) -0.1913(3) 0.0215(7) Uani 1 1 d .
C6 C 0.4886(4) 0.0900(4) -0.1932(3) 0.0306(8) Uani 1 1 d .
H6A H 0.5888 0.0655 -0.1822 0.037 Uiso 1 1 calc R
H6B H 0.5020 0.1770 -0.2111 0.037 Uiso 1 1 calc R
C7 C 0.3845(4) -0.0346(4) -0.2961(3) 0.0298(8) Uani 1 1 d .
H7A H 0.3889 -0.1264 -0.2873 0.036 Uiso 1 1 calc R
H7B H 0.4183 -0.0414 -0.3697 0.036 Uiso 1 1 calc R
C2 C 0.4666(4) 0.2402(4) 0.1278(3) 0.0284(8) Uani 1 1 d .
H2A H 0.5294 0.3000 0.2013 0.034 Uiso 1 1 calc R
C4 C 0.4285(4) 0.1235(4) -0.0814(3) 0.0243(7) Uani 1 1 d .
C5 C 0.2777(4) 0.0750(3) -0.0812(3) 0.0202(7) Uani 1 1 d .
C3 C 0.5229(4) 0.2072(4) 0.0264(3) 0.0272(8) Uani 1 1 d .
H3A H 0.6266 0.2414 0.0296 0.033 Uiso 1 1 calc R
C1 C 0.3150(4) 0.1842(4) 0.1207(3) 0.0260(7) Uani 1 1 d .
H1A H 0.2765 0.2048 0.1910 0.031 Uiso 1 1 calc R
Cl3 Cl -0.29621(13) 0.59075(12) 0.14081(12) 0.0527(3) Uani 1 1 d .
Cl2 Cl -0.27714(14) 0.47110(13) -0.10798(12) 0.0547(3) Uani 1 1 d .
C20 C -0.1772(5) 0.5401(5) 0.0374(4) 0.0422(10) Uani 1 1 d .
H20C H -0.0984 0.6252 0.0509 0.051 Uiso 1 1 calc R
H20A H -0.1264 0.4659 0.0490 0.051 Uiso 1 1 calc 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'
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'
Ni Ni 0.3393 1.1124 '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'
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 Ni1 N1 180.00(18) 2 .
N1 Ni1 N2 103.65(11) 2 .
N1 Ni1 N2 76.35(11) . .
N1 Ni1 N2 76.35(11) 2 2
N1 Ni1 N2 103.65(11) . 2
N2 Ni1 N2 180.00(14) . 2
N1 Ni1 Cl1 87.30(8) 2 2
N1 Ni1 Cl1 92.70(8) . 2
N2 Ni1 Cl1 89.01(8) . 2
N2 Ni1 Cl1 90.99(8) 2 2
N1 Ni1 Cl1 92.70(8) 2 .
N1 Ni1 Cl1 87.30(8) . .
N2 Ni1 Cl1 90.99(8) . .
N2 Ni1 Cl1 89.01(8) 2 .
Cl1 Ni1 Cl1 180.00(4) 2 .
C1 N1 C5 118.3(3) . .
C1 N1 Ni1 125.3(2) . .
C5 N1 Ni1 116.3(2) . .
C9 N2 C10 118.6(3) . .
C9 N2 Ni1 112.1(2) . .
C10 N2 Ni1 129.0(2) . .
O2 N3 O1 123.4(3) . .
O2 N3 C13 118.7(3) . .
O1 N3 C13 117.8(4) . .
C16 C17 H17A 109.5 . .
C16 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C16 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C15 C16 C17 114.4(3) . .
C15 C16 H16A 108.7 . .
C17 C16 H16A 108.7 . .
C15 C16 H16B 108.7 . .
C17 C16 H16B 108.7 . .
H16A C16 H16B 107.6 . .
C13 C14 C15 119.7(3) . .
C13 C14 H14A 120.2 . .
C15 C14 H14A 120.2 . .
C14 C15 C10 118.5(3) . .
C14 C15 C16 119.1(3) . .
C10 C15 C16 122.4(3) . .
C14 C13 C12 122.1(3) . .
C14 C13 N3 119.3(3) . .
C12 C13 N3 118.6(3) . .
C11 C18 C19 113.9(3) . .
C11 C18 H18A 108.8 . .
C19 C18 H18A 108.8 . .
C11 C18 H18B 108.8 . .
C19 C18 H18B 108.8 . .
H18A C18 H18B 107.7 . .
C13 C12 C11 119.7(3) . .
C13 C12 H12A 120.1 . .
C11 C12 H12A 120.1 . .
C12 C11 C10 118.3(3) . .
C12 C11 C18 118.4(3) . .
C10 C11 C18 123.3(3) . .
C11 C10 C15 121.5(3) . .
C11 C10 N2 119.8(3) . .
C15 C10 N2 118.5(3) . .
C18 C19 H19A 109.5 . .
C18 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C18 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C9 C8 C7 111.2(3) . .
C9 C8 H8A 109.4 . .
C7 C8 H8A 109.4 . .
C9 C8 H8B 109.4 . .
C7 C8 H8B 109.4 . .
H8A C8 H8B 108.0 . .
N2 C9 C5 118.5(3) . .
N2 C9 C8 125.4(3) . .
C5 C9 C8 116.0(3) . .
C4 C6 C7 112.4(3) . .
C4 C6 H6A 109.1 . .
C7 C6 H6A 109.1 . .
C4 C6 H6B 109.1 . .
C7 C6 H6B 109.1 . .
H6A C6 H6B 107.9 . .
C6 C7 C8 110.1(3) . .
C6 C7 H7A 109.6 . .
C8 C7 H7A 109.6 . .
C6 C7 H7B 109.6 . .
C8 C7 H7B 109.6 . .
H7A C7 H7B 108.1 . .
C3 C2 C1 118.7(3) . .
C3 C2 H2A 120.7 . .
C1 C2 H2A 120.7 . .
C5 C4 C3 117.6(3) . .
C5 C4 C6 121.9(3) . .
C3 C4 C6 120.5(3) . .
N1 C5 C4 122.7(3) . .
N1 C5 C9 115.8(3) . .
C4 C5 C9 121.4(3) . .
C2 C3 C4 120.2(3) . .
C2 C3 H3A 119.9 . .
C4 C3 H3A 119.9 . .
N1 C1 C2 122.5(3) . .
N1 C1 H1A 118.8 . .
C2 C1 H1A 118.8 . .
Cl2 C20 Cl3 112.3(2) . .
Cl2 C20 H20C 109.1 . .
Cl3 C20 H20C 109.1 . .
Cl2 C20 H20A 109.1 . .
Cl3 C20 H20A 109.1 . .
H20C C20 H20A 107.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 N1 2.083(3) 2
Ni1 N1 2.083(3) .
Ni1 N2 2.256(3) .
Ni1 N2 2.256(3) 2
Ni1 Cl1 2.3601(10) 2
Ni1 Cl1 2.3601(10) .
N1 C1 1.337(4) .
N1 C5 1.356(4) .
N2 C9 1.283(4) .
N2 C10 1.439(4) .
N3 O2 1.228(5) .
N3 O1 1.233(5) .
N3 C13 1.469(5) .
C17 C16 1.532(6) .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C16 C15 1.511(5) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C14 C13 1.381(5) .
C14 C15 1.387(5) .
C14 H14A 0.9500 .
C15 C10 1.418(5) .
C13 C12 1.387(5) .
C18 C11 1.517(5) .
C18 C19 1.530(5) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C12 C11 1.392(5) .
C12 H12A 0.9500 .
C11 C10 1.404(5) .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C8 C9 1.511(4) .
C8 C7 1.528(5) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C5 1.476(5) .
C6 C4 1.506(5) .
C6 C7 1.521(5) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C2 C3 1.372(5) .
C2 C1 1.397(5) .
C2 H2A 0.9500 .
C4 C5 1.393(5) .
C4 C3 1.394(5) .
C3 H3A 0.9500 .
C1 H1A 0.9500 .
Cl3 C20 1.768(5) .
Cl2 C20 1.765(5) .
C20 H20C 0.9900 .
C20 H20A 0.9900 .
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
N1 Ni1 N1 C1 -36(100) 2
N2 Ni1 N1 C1 176.8(3) .
N2 Ni1 N1 C1 -3.2(3) 2
Cl1 Ni1 N1 C1 88.4(3) 2
Cl1 Ni1 N1 C1 -91.6(3) .
N1 Ni1 N1 C5 140(100) 2
N2 Ni1 N1 C5 -8.1(2) .
N2 Ni1 N1 C5 171.9(2) 2
Cl1 Ni1 N1 C5 -96.4(2) 2
Cl1 Ni1 N1 C5 83.6(2) .
N1 Ni1 N2 C9 -175.8(2) 2
N1 Ni1 N2 C9 4.2(2) .
N2 Ni1 N2 C9 140(100) 2
Cl1 Ni1 N2 C9 97.3(2) 2
Cl1 Ni1 N2 C9 -82.7(2) .
N1 Ni1 N2 C10 11.1(3) 2
N1 Ni1 N2 C10 -168.9(3) .
N2 Ni1 N2 C10 -33(100) 2
Cl1 Ni1 N2 C10 -75.8(3) 2
Cl1 Ni1 N2 C10 104.2(3) .
C13 C14 C15 C10 -0.6(5) .
C13 C14 C15 C16 177.0(3) .
C17 C16 C15 C14 107.7(4) .
C17 C16 C15 C10 -74.7(5) .
C15 C14 C13 C12 3.0(5) .
C15 C14 C13 N3 -176.2(3) .
O2 N3 C13 C14 174.4(4) .
O1 N3 C13 C14 -4.2(5) .
O2 N3 C13 C12 -4.7(5) .
O1 N3 C13 C12 176.7(4) .
C14 C13 C12 C11 -1.9(6) .
N3 C13 C12 C11 177.2(3) .
C13 C12 C11 C10 -1.4(5) .
C13 C12 C11 C18 179.0(3) .
C19 C18 C11 C12 -51.2(4) .
C19 C18 C11 C10 129.2(4) .
C12 C11 C10 C15 3.7(5) .
C18 C11 C10 C15 -176.7(3) .
C12 C11 C10 N2 -171.0(3) .
C18 C11 C10 N2 8.6(5) .
C14 C15 C10 C11 -2.7(5) .
C16 C15 C10 C11 179.7(3) .
C14 C15 C10 N2 172.1(3) .
C16 C15 C10 N2 -5.5(5) .
C9 N2 C10 C11 -81.2(4) .
Ni1 N2 C10 C11 91.5(3) .
C9 N2 C10 C15 103.9(4) .
Ni1 N2 C10 C15 -83.4(4) .
C10 N2 C9 C5 173.8(3) .
Ni1 N2 C9 C5 0.0(4) .
C10 N2 C9 C8 -3.0(5) .
Ni1 N2 C9 C8 -176.9(3) .
C7 C8 C9 N2 -144.8(3) .
C7 C8 C9 C5 38.2(4) .
C4 C6 C7 C8 49.0(4) .
C9 C8 C7 C6 -59.9(4) .
C7 C6 C4 C5 -17.6(5) .
C7 C6 C4 C3 163.6(3) .
C1 N1 C5 C4 2.5(5) .
Ni1 N1 C5 C4 -173.0(2) .
C1 N1 C5 C9 -173.7(3) .
Ni1 N1 C5 C9 10.8(4) .
C3 C4 C5 N1 -1.9(5) .
C6 C4 C5 N1 179.2(3) .
C3 C4 C5 C9 174.1(3) .
C6 C4 C5 C9 -4.8(5) .
N2 C9 C5 N1 -6.9(4) .
C8 C9 C5 N1 170.2(3) .
N2 C9 C5 C4 176.8(3) .
C8 C9 C5 C4 -6.0(5) .
C1 C2 C3 C4 2.2(5) .
C5 C4 C3 C2 -0.5(5) .
C6 C4 C3 C2 178.4(3) .
C5 N1 C1 C2 -0.6(5) .
Ni1 N1 C1 C2 174.4(3) .
C3 C2 C1 N1 -1.7(5) .
