#------------------------------------------------------------------------------
#$Date: 2016-03-23 23:39:14 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179510 $
#$URL: svn://www.crystallography.net/cod/cif/4/34/07/4340746.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_4340746
loop_
_publ_author_name
'Kramer, Wesley W.'
'Cameron, Lindsay A.'
'Zarkesh, Ryan A.'
'Ziller, Joseph W.'
'Heyduk, Alan F.'
_publ_section_title
;
 Donor-Acceptor Ligand-to-Ligand Charge-Transfer Coordination Complexes of
 Nickel(II).
;
_journal_issue                   16
_journal_name_full               'Inorganic chemistry'
_journal_page_first              8825
_journal_page_last               8837
_journal_paper_doi               10.1021/ic5017214
_journal_volume                  53
_journal_year                    2014
_chemical_formula_sum            'C44 H36 N2 Ni O2'
_chemical_formula_weight         683.46
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 109.2445(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.5572(17)
_cell_length_b                   23.260(2)
_cell_length_c                   8.5639(8)
_cell_measurement_reflns_used    6327
_cell_measurement_temperature    88(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.46
_cell_volume                     3301.9(5)
_computing_cell_refinement       'Bruker SAINT 8.34a, 2013'
_computing_data_collection       'Bruker APEX2 2013.10-0, 2013'
_computing_data_reduction        'Bruker SAINT 8.34a, 2013'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL 2013/1'
_diffrn_ambient_temperature      88(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            18153
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.005
_diffrn_reflns_theta_min         1.508
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS 2012/1'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    not_measured
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1432
_exptl_crystal_size_max          0.365
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.762
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4182
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0390
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0605P)²+2.3573P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1067
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3662
_reflns_number_total             4182
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic5017214_si_002.cif
_cod_data_source_block           afh420_3b
_cod_depositor_comments
;Adding full bibliography for 4340739--4340747.cif.

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 
;
_cod_database_code               4340746
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.803
_shelx_estimated_absorpt_t_max   0.940
_shelxl_version_number           2014-2
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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'
'-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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Ni1 Ni 0.0000 0.75842(2) 0.7500 0.01649(10) Uani 1 2 d S T P
O1 O 0.06346(7) 0.70269(5) 0.70768(14) 0.0201(2) Uani 1 1 d . . .
N1 N 0.07095(8) 0.81797(6) 0.73989(17) 0.0183(3) Uani 1 1 d . . .
C1 C 0.03349(9) 0.65080(7) 0.7250(2) 0.0192(3) Uani 1 1 d . . .
C2 C 0.06811(10) 0.59824(7) 0.6927(2) 0.0220(3) Uani 1 1 d . . .
C3 C 0.13313(11) 0.59850(8) 0.6305(2) 0.0264(4) Uani 1 1 d . . .
H3A H 0.1555 0.6341 0.6128 0.032 Uiso 1 1 calc R U .
C4 C 0.16441(12) 0.54812(9) 0.5952(2) 0.0341(4) Uani 1 1 d . . .
H4A H 0.2069 0.5488 0.5496 0.041 Uiso 1 1 calc R U .
C5 C 0.13328(12) 0.49548(9) 0.6268(3) 0.0365(5) Uani 1 1 d . . .
H5A H 0.1563 0.4605 0.6066 0.044 Uiso 1 1 calc R U .
C6 C 0.06978(12) 0.49432(8) 0.6868(2) 0.0329(4) Uani 1 1 d . . .
H6A H 0.0491 0.4583 0.7063 0.040 Uiso 1 1 calc R U .
C7 C 0.03435(10) 0.54534(7) 0.7202(2) 0.0249(4) Uani 1 1 d . . .
C8 C 0.04050(9) 0.86877(7) 0.7437(2) 0.0207(3) Uani 1 1 d . . .
C9 C 0.06553(10) 0.92836(7) 0.7365(2) 0.0253(4) Uani 1 1 d . . .
C10 C 0.13106(11) 0.95553(8) 0.7151(3) 0.0303(4) Uani 1 1 d . . .
H10A H 0.1757 0.9341 0.7072 0.036 Uiso 1 1 calc R U .
C11 C 0.12996(12) 1.01622(8) 0.7052(3) 0.0380(5) Uani 1 1 d . . .
H11A H 0.1737 1.0354 0.6853 0.046 Uiso 1 1 calc R U .
C12 C 0.06768(12) 1.04861(9) 0.7235(3) 0.0403(5) Uani 1 1 d . . .
H12A H 0.0699 1.0893 0.7182 0.048 Uiso 1 1 calc R U .
C13 C 0.0000 1.02188(11) 0.7500 0.0337(6) Uani 1 2 d S T P
C14 C 0.0000 0.96190(10) 0.7500 0.0273(5) Uani 1 2 d S T P
C15 C 0.15467(9) 0.81536(7) 0.7515(2) 0.0182(3) Uani 1 1 d . . .
C16 C 0.21258(10) 0.82131(7) 0.9079(2) 0.0198(3) Uani 1 1 d . . .
C17 C 0.29320(10) 0.82439(7) 0.9178(2) 0.0218(3) Uani 1 1 d . . .
H17A H 0.3335 0.8285 1.0231 0.026 Uiso 1 1 calc R U .
C18 C 0.31628(9) 0.82163(7) 0.7767(2) 0.0219(3) Uani 1 1 d . . .
C19 C 0.25693(10) 0.81350(7) 0.6243(2) 0.0236(3) Uani 1 1 d . . .
H19A H 0.2723 0.8102 0.5282 0.028 Uiso 1 1 calc R U .
C20 C 0.17503(10) 0.81004(7) 0.6080(2) 0.0211(3) Uani 1 1 d . . .
C21 C 0.18949(11) 0.82542(8) 1.0625(2) 0.0260(4) Uani 1 1 d . . .
H21A H 0.1447 0.7991 1.0536 0.039 Uiso 1 1 calc R U .
H21B H 0.1729 0.8649 1.0753 0.039 Uiso 1 1 calc R U .
H21C H 0.2359 0.8149 1.1588 0.039 Uiso 1 1 calc R U .
C22 C 0.40489(10) 0.82617(8) 0.7956(2) 0.0288(4) Uani 1 1 d . . .
H22A H 0.4106 0.8343 0.6877 0.043 Uiso 1 1 calc R U .
H22B H 0.4319 0.7898 0.8385 0.043 Uiso 1 1 calc R U .
H22C H 0.4295 0.8573 0.8727 0.043 Uiso 1 1 calc R U .
C23 C 0.11022(10) 0.80224(9) 0.4431(2) 0.0304(4) Uani 1 1 d . . .
H23A H 0.0797 0.7672 0.4451 0.046 Uiso 1 1 calc R U .
H23B H 0.1350 0.7991 0.3563 0.046 Uiso 1 1 calc R U .
H23C H 0.0738 0.8354 0.4205 0.046 Uiso 1 1 calc R U .
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 Ni1 O1 89.28(7) . 2_556
O1 Ni1 N1 171.61(5) . 2_556
O1 Ni1 N1 93.27(5) 2_556 2_556
O1 Ni1 N1 93.27(5) . .
O1 Ni1 N1 171.61(5) 2_556 .
N1 Ni1 N1 85.35(8) 2_556 .
C1 O1 Ni1 109.26(9) . .
C8 N1 C15 117.02(13) . .
C8 N1 Ni1 112.52(10) . .
C15 N1 Ni1 129.84(11) . .
O1 C1 C1 116.06(8) . 2_556
O1 C1 C2 122.62(14) . .
C1 C1 C2 121.32(9) 2_556 .
C3 C2 C7 120.06(16) . .
C3 C2 C1 121.14(16) . .
C7 C2 C1 118.77(15) . .
C4 C3 C2 120.88(18) . .
C3 C4 C5 119.61(19) . .
C6 C5 C4 120.35(18) . .
C5 C6 C7 121.70(19) . .
C6 C7 C2 117.33(17) . .
C6 C7 C7 122.82(12) . 2_556
C2 C7 C7 119.85(10) . 2_556
N1 C8 C8 114.81(9) . 2_556
N1 C8 C9 136.73(14) . .
C8 C8 C9 108.46(9) 2_556 .
C10 C9 C14 119.44(17) . .
C10 C9 C8 135.81(16) . .
C14 C9 C8 104.69(15) . .
C9 C10 C11 118.08(18) . .
C12 C11 C10 122.32(18) . .
C11 C12 C13 120.95(19) . .
C14 C13 C12 115.88(13) . .
C14 C13 C12 115.88(13) . 2_556
C12 C13 C12 128.2(3) . 2_556
C13 C14 C9 123.17(11) . 2_556
C13 C14 C9 123.17(11) . .
C9 C14 C9 113.7(2) 2_556 .
C20 C15 C16 122.49(14) . .
C20 C15 N1 119.65(14) . .
C16 C15 N1 117.78(14) . .
C17 C16 C15 117.94(15) . .
C17 C16 C21 120.31(15) . .
C15 C16 C21 121.74(14) . .
C16 C17 C18 121.60(16) . .
C19 C18 C17 118.52(14) . .
C19 C18 C22 122.43(15) . .
C17 C18 C22 119.03(16) . .
C18 C19 C20 121.96(15) . .
C15 C20 C19 117.40(15) . .
C15 C20 C23 120.26(14) . .
C19 C20 C23 122.32(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 O1 1.8219(11) .
Ni1 O1 1.8220(11) 2_556
Ni1 N1 1.8837(13) 2_556
Ni1 N1 1.8837(13) .
O1 C1 1.3441(19) .
N1 C8 1.302(2) .
N1 C15 1.4413(19) .
C1 C1 1.378(3) 2_556
C1 C2 1.432(2) .
C2 C3 1.410(2) .
C2 C7 1.419(2) .
C3 C4 1.370(3) .
C4 C5 1.403(3) .
C5 C6 1.373(3) .
C6 C7 1.412(2) .
C7 C7 1.456(4) 2_556
C8 C8 1.461(3) 2_556
C8 C9 1.461(2) .
C9 C10 1.377(2) .
C9 C14 1.426(2) .
C10 C11 1.414(3) .
C11 C12 1.378(3) .
C12 C13 1.424(2) .
C13 C14 1.395(3) .
C13 C12 1.424(2) 2_556
C14 C9 1.426(2) 2_556
C15 C20 1.394(2) .
C15 C16 1.396(2) .
C16 C17 1.392(2) .
C16 C21 1.510(2) .
C17 C18 1.397(2) .
C18 C19 1.389(2) .
C18 C22 1.514(2) .
C19 C20 1.401(2) .
C20 C23 1.504(2) .
