#------------------------------------------------------------------------------
#$Date: 2016-03-21 12:45:10 +0100 (lun 21 de mar de 2016) $
#$Revision: 178699 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/10/4081087.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_4081087
loop_
_publ_author_name
'Yuan, Jianchao'
'Wang, Fuzhou'
'Xu, Weibing'
'Mei, Tongjian'
'Li, Jing'
'Yuan, Bingnian'
'Song, Fengying'
'Jia, Zong'
_publ_section_title
;
 Chiral Naphthyl-α-diimine Nickel(II) Catalysts Bearingsec-Phenethyl
 Groups: Chain-Walking Polymerization of Ethylene at High Temperature and
 Stereoselective Polymerization of Methyl Methacrylate at Low Temperature
;
_journal_issue                   14
_journal_name_full               Organometallics
_journal_page_first              3960
_journal_paper_doi               10.1021/om400433t
_journal_volume                  32
_journal_year                    2013
_chemical_formula_moiety         'C34 H24 Br2 N2 Ni'
_chemical_formula_sum            'C34 H24 Br2 N2 Ni'
_chemical_formula_weight         679.08
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-05-20
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_audit_update_record
;
2013-05-21 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.964(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.646(4)
_cell_length_b                   11.889(5)
_cell_length_c                   14.387(6)
_cell_measurement_reflns_used    2710
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.46
_cell_measurement_theta_min      2.23
_cell_volume                     1634.0(12)
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11489
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.23
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.062
_exptl_absorpt_correction_T_max  0.5939
_exptl_absorpt_correction_T_min  0.5149
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_platon_squeeze_details
;
;
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         3048
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.955
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0358
_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)+(0.0439P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0827
_reflns_number_gt                2026
_reflns_number_total             3048
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400433t_si_002.cif
_cod_data_source_block           2d
_cod_original_cell_volume        1634.0(11)
_cod_database_code               4081087
#BEGIN Tags that were not found in dictionaries:
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C14(H14), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y, 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 0.2500 0.41269(4) 0.7500 0.03840(17) Uani 1 2 d S
Br1 Br 0.05895(4) 0.50864(3) 0.67199(2) 0.05748(15) Uani 1 1 d .
C1 C 0.0479(3) 0.3283(2) 0.94409(19) 0.0342(7) Uani 1 1 d .
C2 C -0.0628(3) 0.3415(3) 0.8707(2) 0.0426(8) Uani 1 1 d .
H2 H -0.0483 0.3252 0.8096 0.051 Uiso 1 1 calc R
C3 C -0.1903(3) 0.3776(3) 0.8872(2) 0.0499(9) Uani 1 1 d .
H3 H -0.2622 0.3855 0.8374 0.060 Uiso 1 1 calc R
C4 C -0.2148(4) 0.4032(3) 0.9780(2) 0.0517(9) Uani 1 1 d .
H4 H -0.3021 0.4296 0.9883 0.062 Uiso 1 1 calc R
C5 C -0.1126(4) 0.3898(3) 1.0506(2) 0.0473(9) Uani 1 1 d .
H5 H -0.1304 0.4066 1.1109 0.057 Uiso 1 1 calc R
C6 C 0.0215(3) 0.3505(2) 1.0371(2) 0.0397(8) Uani 1 1 d .
C7 C 0.1306(4) 0.3336(3) 1.1114(2) 0.0537(10) Uani 1 1 d .
H7 H 0.1145 0.3469 1.1727 0.064 Uiso 1 1 calc R
C8 C 0.2581(4) 0.2984(3) 1.0954(2) 0.0544(9) Uani 1 1 d .
H8 H 0.3274 0.2873 1.1463 0.065 Uiso 1 1 calc R
C9 C 0.2900(3) 0.2780(3) 1.0040(2) 0.0428(8) Uani 1 1 d .
C10 C 0.1844(3) 0.2945(2) 0.93160(19) 0.0352(7) Uani 1 1 d .
C11 C 0.4365(4) 0.2443(3) 0.9917(2) 0.0631(10) Uani 1 1 d .
H11A H 0.4431 0.1638 0.9906 0.095 Uiso 1 1 calc R
H11B H 0.5009 0.2733 1.0430 0.095 Uiso 1 1 calc R
H11C H 0.4591 0.2743 0.9337 0.095 Uiso 1 1 calc R
C12 C 0.2315(3) 0.1895(2) 0.79879(19) 0.0355(7) Uani 1 1 d .
C13 C 0.2216(3) 0.0719(3) 0.8278(2) 0.0464(8) Uani 1 1 d .
C14 C 0.1917(5) 0.0181(3) 0.9062(3) 0.0662(11) Uani 1 1 d .
H14 H 0.1717 0.0583 0.9581 0.079 Uiso 1 1 calc R
C15 C 0.1921(5) -0.1005(3) 0.9062(3) 0.0871(14) Uani 1 1 d .
H15 H 0.1716 -0.1380 0.9593 0.104 Uiso 1 1 calc R
C16 C 0.2210(5) -0.1617(3) 0.8323(3) 0.0916(15) Uani 1 1 d .
H16 H 0.2215 -0.2398 0.8361 0.110 Uiso 1 1 calc R
C17 C 0.2500 -0.1095(4) 0.7500 0.0737(17) Uani 1 2 d S
C18 C 0.2500 0.0086(4) 0.7500 0.0521(13) Uani 1 2 d S
N1 N 0.2136(2) 0.2850(2) 0.83627(15) 0.0350(6) 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'
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'
Br Br -0.2901 2.4595 '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
Br1 Ni1 Br1 121.10(4) . 2_556
N1 Ni1 Br1 118.18(7) 2_556 2_556
N1 Ni1 Br1 105.43(7) . 2_556
N1 Ni1 Br1 105.43(7) 2_556 .
N1 Ni1 Br1 118.18(7) . .
N1 Ni1 N1 82.67(13) 2_556 .
C2 C1 C6 118.1(3) . .
C2 C1 C10 124.2(3) . .
C10 C1 C6 117.7(3) . .
C1 C2 H2 119.4 . .
C3 C2 C1 121.3(3) . .
C3 C2 H2 119.4 . .
C2 C3 H3 119.7 . .
C2 C3 C4 120.6(3) . .
C4 C3 H3 119.7 . .
C3 C4 H4 119.9 . .
C5 C4 C3 120.1(3) . .
C5 C4 H4 119.9 . .
C4 C5 H5 119.3 . .
C4 C5 C6 121.3(3) . .
C6 C5 H5 119.3 . .
C5 C6 C1 118.5(3) . .
C7 C6 C1 118.4(3) . .
C7 C6 C5 123.1(3) . .
C6 C7 H7 119.4 . .
C8 C7 C6 121.3(3) . .
C8 C7 H7 119.4 . .
C7 C8 H8 118.9 . .
C7 C8 C9 122.2(3) . .
C9 C8 H8 118.9 . .
C8 C9 C11 119.0(3) . .
C10 C9 C8 116.7(3) . .
C10 C9 C11 124.2(3) . .
C1 C10 N1 116.9(3) . .
C9 C10 C1 123.6(3) . .
C9 C10 N1 119.4(3) . .
C9 C11 H11A 109.5 . .
C9 C11 H11B 109.5 . .
C9 C11 H11C 109.5 . .
H11A C11 H11B 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C13 C12 C12 107.48(16) . 2_556
N1 C12 C12 117.35(16) . 2_556
N1 C12 C13 135.1(3) . .
C14 C13 C12 135.5(3) . .
C14 C13 C18 119.6(3) . .
C18 C13 C12 104.9(3) . .
C13 C14 H14 121.0 . .
C13 C14 C15 118.0(3) . .
C15 C14 H14 121.0 . .
C14 C15 H15 118.6 . .
C16 C15 C14 122.8(3) . .
C16 C15 H15 118.6 . .
C15 C16 H16 119.5 . .
C15 C16 C17 121.0(4) . .
C17 C16 H16 119.5 . .
C16 C17 C16 127.3(5) . 2_556
C16 C17 C18 116.3(3) 2_556 .
C16 C17 C18 116.3(3) . .
C13 C18 C13 115.3(4) . 2_556
C17 C18 C13 122.34(19) . 2_556
C17 C18 C13 122.34(19) . .
C10 N1 Ni1 126.73(19) . .
C12 N1 Ni1 111.28(18) . .
C12 N1 C10 121.7(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 Br1 2.3203(7) 2_556
Ni1 Br1 2.3203(7) .
Ni1 N1 2.023(2) .
Ni1 N1 2.023(2) 2_556
C1 C2 1.402(4) .
C1 C6 1.421(4) .
C1 C10 1.412(4) .
C2 H2 0.9300 .
C2 C3 1.354(4) .
C3 H3 0.9300 .
C3 C4 1.393(4) .
C4 H4 0.9300 .
C4 C5 1.343(5) .
C5 H5 0.9300 .
C5 C6 1.414(4) .
C6 C7 1.407(5) .
C7 H7 0.9300 .
C7 C8 1.348(5) .
C8 H8 0.9300 .
C8 C9 1.413(4) .
C9 C10 1.366(4) .
C9 C11 1.503(4) .
C10 N1 1.442(3) .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 C12 1.496(5) 2_556
C12 C13 1.465(4) .
C12 N1 1.279(3) .
C13 C14 1.362(4) .
C13 C18 1.406(4) .
C14 H14 0.9300 .
C14 C15 1.409(5) .
C15 H15 0.9300 .
C15 C16 1.349(5) .
C16 H16 0.9300 .
C16 C17 1.399(4) .
C17 C16 1.399(4) 2_556
C17 C18 1.405(6) .
C18 C13 1.406(4) 2_556
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
_geom_torsion_site_symmetry_4
Br1 Ni1 N1 C10 57.9(2) 2_556 .
Br1 Ni1 N1 C10 -81.2(2) . .
Br1 Ni1 N1 C12 104.5(2) . .
Br1 Ni1 N1 C12 -116.4(2) 2_556 .
C1 C2 C3 C4 0.3(5) . .
C1 C6 C7 C8 0.7(5) . .
C1 C10 N1 Ni1 76.9(3) . .
C1 C10 N1 C12 -109.4(3) . .
C2 C1 C6 C5 -2.9(4) . .
C2 C1 C6 C7 177.8(3) . .
C2 C1 C10 C9 -177.5(3) . .
C2 C1 C10 N1 6.9(4) . .
C2 C3 C4 C5 -1.5(5) . .
C3 C4 C5 C6 0.4(5) . .
C4 C5 C6 C1 1.8(4) . .
C4 C5 C6 C7 -178.9(3) . .
C5 C6 C7 C8 -178.5(3) . .
C6 C1 C2 C3 2.0(4) . .
C6 C1 C10 C9 2.5(4) . .
C6 C1 C10 N1 -173.0(2) . .
C6 C7 C8 C9 0.8(5) . .
C7 C8 C9 C10 -0.6(5) . .
C7 C8 C9 C11 177.1(3) . .
C8 C9 C10 C1 -1.1(5) . .
C8 C9 C10 N1 174.4(3) . .
C9 C10 N1 Ni1 -98.9(3) . .
C9 C10 N1 C12 74.8(4) . .
C10 C1 C2 C3 -178.0(3) . .
C10 C1 C6 C5 177.0(3) . .
C10 C1 C6 C7 -2.3(4) . .
C11 C9 C10 C1 -178.7(3) . .
C11 C9 C10 N1 -3.2(5) . .
C12 C12 C13 C14 -179.6(4) 2_556 .
C12 C12 C13 C18 -0.6(4) 2_556 .
C12 C12 N1 Ni1 -2.3(4) 2_556 .
C12 C12 N1 C10 -177.0(3) 2_556 .
C12 C13 C14 C15 179.6(4) . .
C12 C13 C18 C13 0.25(15) . 2_556
C12 C13 C18 C17 -179.75(15) . .
C13 C12 N1 Ni1 179.4(3) . .
C13 C12 N1 C10 4.7(5) . .
C13 C14 C15 C16 0.1(7) . .
C14 C13 C18 C13 179.4(4) . 2_556
C14 C13 C18 C17 -0.6(4) . .
C14 C15 C16 C17 -1.2(8) . .
C15 C16 C17 C16 -178.8(5) . 2_556
C15 C16 C17 C18 1.2(5) . .
C16 C17 C18 C13 -0.4(3) . .
C16 C17 C18 C13 -0.4(3) 2_556 2_556
C16 C17 C18 C13 179.6(3) 2_556 .
C16 C17 C18 C13 179.6(3) . 2_556
C18 C13 C14 C15 0.7(6) . .
N1 Ni1 N1 C10 175.2(3) 2_556 .
N1 Ni1 N1 C12 0.88(16) 2_556 .
N1 C12 C13 C14 -1.2(7) . .
N1 C12 C13 C18 177.8(3) . .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.249 -0.022 0.250 172 38 ' '
2 -0.251 1.022 0.750 172 38 ' '
