#------------------------------------------------------------------------------
#$Date: 2016-03-25 23:22:32 +0200 (Fri, 25 Mar 2016) $
#$Revision: 180036 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/30/7033078.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_7033078
loop_
_publ_author_name
'Ohno, Keiji'
'Nagasawa, Akira'
'Fujihara, Takashi'
_publ_section_title
;
 Dinuclear nickel(II) complexes with 2,5-diamino-1,4-benzoquinonediimine
 ligands as precatalysts for the polymerization of styrene: electronic and
 steric substituent effects.
;
_journal_issue                   1
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              368
_journal_page_last               376
_journal_paper_doi               10.1039/c4dt02858a
_journal_volume                  44
_journal_year                    2015
_chemical_formula_sum            'C38 H40 N4 O4'
_chemical_formula_weight         616.74
_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                 99.173(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.680(9)
_cell_length_b                   9.276(7)
_cell_length_c                   16.587(13)
_cell_measurement_reflns_used    2095
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.49
_cell_volume                     1622(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      173(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.1054
_diffrn_reflns_av_unetI/netI     0.0751
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10836
_diffrn_reflns_theta_full        27.86
_diffrn_reflns_theta_max         27.86
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9869
_exptl_absorpt_correction_T_min  0.9693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3814
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1476
_refine_ls_R_factor_gt           0.0697
_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)+(0.0654P)²+0.5437P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1499
_refine_ls_wR_factor_ref         0.1846
_reflns_number_gt                1856
_reflns_number_total             3814
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4dt02858a2.cif
_cod_data_source_block           2-OEtApH2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

 Adding full bibliography for 7033073--7033079.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7033078
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
C1 C 0.3801(2) 0.4906(3) 1.02698(15) 0.0413(7) Uani 1 1 d .
C2 C 0.4125(2) 0.6151(3) 0.97777(15) 0.0389(7) Uani 1 1 d .
C3 C 0.5350(2) 0.6153(3) 0.95210(15) 0.0438(7) Uani 1 1 d .
H3 H 0.5561 0.6910 0.9200 0.053 Uiso 1 1 calc R
C4 C 0.1820(2) 0.3885(3) 1.06602(15) 0.0419(7) Uani 1 1 d .
C5 C 0.0764(2) 0.4309(4) 1.10017(16) 0.0438(7) Uani 1 1 d .
C6 C -0.0095(3) 0.3303(4) 1.11646(18) 0.0568(9) Uani 1 1 d .
H6 H -0.0799 0.3590 1.1390 0.068 Uiso 1 1 calc R
C7 C 0.0070(3) 0.1878(4) 1.1000(2) 0.0653(10) Uani 1 1 d .
H7 H -0.0516 0.1200 1.1118 0.078 Uiso 1 1 calc R
C8 C 0.1101(3) 0.1445(4) 1.0659(2) 0.0625(9) Uani 1 1 d .
H8 H 0.1214 0.0478 1.0541 0.075 Uiso 1 1 calc R
C9 C 0.1965(3) 0.2464(4) 1.04942(18) 0.0527(8) Uani 1 1 d .
H9 H 0.2663 0.2173 1.0264 0.063 Uiso 1 1 calc R
C10 C -0.0322(3) 0.6254(4) 1.1528(2) 0.0640(10) Uani 1 1 d .
H10A H -0.0277 0.5803 1.2060 0.077 Uiso 1 1 calc R
H10B H -0.1138 0.6026 1.1206 0.077 Uiso 1 1 calc R
C11 C -0.0170(3) 0.7836(4) 1.1619(2) 0.0763(11) Uani 1 1 d .
H11A H 0.0637 0.8048 1.1942 0.115 Uiso 1 1 calc R
H11B H -0.0835 0.8216 1.1885 0.115 Uiso 1 1 calc R
H11C H -0.0215 0.8270 1.1090 0.115 Uiso 1 1 calc R
C12 C 0.3384(2) 0.8237(3) 0.90671(17) 0.0425(7) Uani 1 1 d .
C13 C 0.3197(2) 0.7946(4) 0.82343(18) 0.0489(8) Uani 1 1 d .
C14 C 0.3163(3) 0.9045(5) 0.7683(2) 0.0648(10) Uani 1 1 d .
H14 H 0.3025 0.8846 0.7126 0.078 Uiso 1 1 calc R
C15 C 0.3332(3) 1.0435(5) 0.7948(2) 0.0710(11) Uani 1 1 d .
H15 H 0.3309 1.1180 0.7571 0.085 Uiso 1 1 calc R
C16 C 0.3534(3) 1.0739(4) 0.8765(2) 0.0691(10) Uani 1 1 d .
H16 H 0.3667 1.1684 0.8945 0.083 Uiso 1 1 calc R
C17 C 0.3541(3) 0.9627(4) 0.9318(2) 0.0549(8) Uani 1 1 d .
H17 H 0.3655 0.9834 0.9874 0.066 Uiso 1 1 calc R
C18 C 0.3403(3) 0.6025(5) 0.7303(2) 0.0810(12) Uani 1 1 d .
H18A H 0.4226 0.6420 0.7248 0.097 Uiso 1 1 calc R
H18B H 0.2798 0.6325 0.6833 0.097 Uiso 1 1 calc R
C19 C 0.3469(4) 0.4437(5) 0.7342(3) 0.1031(15) Uani 1 1 d .
H19A H 0.4025 0.4149 0.7828 0.155 Uiso 1 1 calc R
H19B H 0.3788 0.4075 0.6872 0.155 Uiso 1 1 calc R
H19C H 0.2637 0.4052 0.7351 0.155 Uiso 1 1 calc R
N1 N 0.2611(2) 0.4987(3) 1.04571(15) 0.0480(7) Uani 1 1 d .
N2 N 0.32712(19) 0.7116(3) 0.96198(14) 0.0459(6) Uani 1 1 d .
O1 O 0.06799(16) 0.5741(3) 1.11292(12) 0.0534(6) Uani 1 1 d .
O2 O 0.3020(2) 0.6533(3) 0.80297(13) 0.0690(7) Uani 1 1 d .
H1 H 0.227(3) 0.583(4) 1.0362(19) 0.062(11) 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'
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
C3 C1 N1 126.8(3) 3_667
C3 C1 C2 120.2(2) 3_667
N1 C1 C2 113.0(2) .
N2 C2 C3 126.3(3) .
N2 C2 C1 115.9(2) .
C3 C2 C1 117.7(2) .
C1 C3 C2 122.0(3) 3_667
C1 C3 H3 119.0 3_667
C2 C3 H3 119.0 .
C9 C4 C5 118.7(3) .
C9 C4 N1 124.5(2) .
C5 C4 N1 116.6(3) .
O1 C5 C6 125.3(3) .
O1 C5 C4 114.7(2) .
C6 C5 C4 119.9(3) .
C5 C6 C7 120.6(3) .
C5 C6 H6 119.7 .
C7 C6 H6 119.7 .
C6 C7 C8 120.1(3) .
C6 C7 H7 119.9 .
C8 C7 H7 119.9 .
C7 C8 C9 119.1(3) .
C7 C8 H8 120.4 .
C9 C8 H8 120.4 .
C4 C9 C8 121.5(3) .
C4 C9 H9 119.3 .
C8 C9 H9 119.3 .
O1 C10 C11 107.5(3) .
O1 C10 H10A 110.2 .
C11 C10 H10A 110.2 .
O1 C10 H10B 110.2 .
C11 C10 H10B 110.2 .
H10A C10 H10B 108.5 .
C10 C11 H11A 109.5 .
C10 C11 H11B 109.5 .
H11A C11 H11B 109.5 .
C10 C11 H11C 109.5 .
H11A C11 H11C 109.5 .
H11B C11 H11C 109.5 .
C17 C12 C13 118.7(3) .
C17 C12 N2 121.5(3) .
C13 C12 N2 119.5(3) .
O2 C13 C14 124.3(3) .
O2 C13 C12 115.3(3) .
C14 C13 C12 120.4(3) .
C15 C14 C13 120.0(3) .
C15 C14 H14 120.0 .
C13 C14 H14 120.0 .
C16 C15 C14 120.4(3) .
C16 C15 H15 119.8 .
C14 C15 H15 119.8 .
C15 C16 C17 119.3(4) .
C15 C16 H16 120.4 .
C17 C16 H16 120.4 .
C12 C17 C16 121.2(3) .
C12 C17 H17 119.4 .
C16 C17 H17 119.4 .
O2 C18 C19 108.2(4) .
O2 C18 H18A 110.1 .
C19 C18 H18A 110.1 .
O2 C18 H18B 110.1 .
C19 C18 H18B 110.1 .
H18A C18 H18B 108.4 .
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 .
C1 N1 C4 129.5(3) .
C1 N1 H1 113(2) .
C4 N1 H1 117(2) .
C2 N2 C12 121.4(2) .
C5 O1 C10 118.3(2) .
C13 O2 C18 119.1(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C3 1.344(4) 3_667
C1 N1 1.358(3) .
C1 C2 1.486(4) .
C2 N2 1.275(3) .
C2 C3 1.439(3) .
C3 C1 1.344(4) 3_667
C3 H3 0.9300 .
C4 C9 1.360(4) .
C4 C5 1.397(4) .
C4 N1 1.401(4) .
C5 O1 1.350(4) .
C5 C6 1.365(4) .
C6 C7 1.367(5) .
C6 H6 0.9300 .
C7 C8 1.375(4) .
C7 H7 0.9300 .
C8 C9 1.378(4) .
C8 H8 0.9300 .
C9 H9 0.9300 .
C10 O1 1.427(3) .
C10 C11 1.481(5) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 C17 1.358(4) .
C12 C13 1.390(4) .
C12 N2 1.404(4) .
C13 O2 1.360(4) .
C13 C14 1.366(5) .
C14 C15 1.366(5) .
C14 H14 0.9300 .
C15 C16 1.366(5) .
C15 H15 0.9300 .
C16 C17 1.380(5) .
C16 H16 0.9300 .
C17 H17 0.9300 .
C18 O2 1.414(4) .
C18 C19 1.476(6) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
N1 H1 0.87(3) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 O1 0.87(3) 2.28(3) 2.592(3) 101(2)
N1 H1 N2 0.87(3) 2.12(3) 2.576(4) 112(3)
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
C3 C1 C2 N2 -178.8(3) 3_667 .
N1 C1 C2 N2 1.6(3) . .
C3 C1 C2 C3 1.7(4) 3_667 .
N1 C1 C2 C3 -178.0(2) . .
N2 C2 C3 C1 178.8(3) . 3_667
C1 C2 C3 C1 -1.7(4) . 3_667
C9 C4 C5 O1 -178.6(2) . .
N1 C4 C5 O1 -3.2(3) . .
C9 C4 C5 C6 0.2(4) . .
N1 C4 C5 C6 175.6(2) . .
O1 C5 C6 C7 178.9(3) . .
C4 C5 C6 C7 0.3(4) . .
C5 C6 C7 C8 -0.7(5) . .
C6 C7 C8 C9 0.6(5) . .
C5 C4 C9 C8 -0.3(4) . .
N1 C4 C9 C8 -175.3(3) . .
C7 C8 C9 C4 -0.1(5) . .
C17 C12 C13 O2 -178.7(2) . .
N2 C12 C13 O2 -5.4(3) . .
C17 C12 C13 C14 -0.6(4) . .
N2 C12 C13 C14 172.7(2) . .
O2 C13 C14 C15 178.9(3) . .
C12 C13 C14 C15 1.0(4) . .
C13 C14 C15 C16 0.0(5) . .
C14 C15 C16 C17 -1.3(5) . .
C13 C12 C17 C16 -0.8(4) . .
N2 C12 C17 C16 -174.0(3) . .
C15 C16 C17 C12 1.8(5) . .
C3 C1 N1 C4 -22.8(5) 3_667 .
C2 C1 N1 C4 156.7(3) . .
C9 C4 N1 C1 -19.0(5) . .
C5 C4 N1 C1 166.0(3) . .
C3 C2 N2 C12 8.7(4) . .
C1 C2 N2 C12 -170.8(2) . .
C17 C12 N2 C2 -112.8(3) . .
C13 C12 N2 C2 74.1(3) . .
C6 C5 O1 C10 5.6(4) . .
C4 C5 O1 C10 -175.7(2) . .
C11 C10 O1 C5 177.9(3) . .
C14 C13 O2 C18 31.3(4) . .
C12 C13 O2 C18 -150.7(3) . .
C19 C18 O2 C13 163.4(3) . .
