#------------------------------------------------------------------------------
#$Date: 2016-03-23 22:23:43 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179479 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/76/4337685.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_4337685
loop_
_publ_author_name
'Merten, Christian'
'McDonald, Robert'
'Xu, Yunjie'
_publ_section_title
;
 Strong Solvent-Dependent Preference of Δ and Λ Stereoisomers of a
 Tris(diamine)nickel(II) Complex Revealed by Vibrational Circular
 Dichroism Spectroscopy.
;
_journal_issue                   6
_journal_name_full               'Inorganic chemistry'
_journal_page_first              3177
_journal_page_last               3182
_journal_paper_doi               10.1021/ic4031766
_journal_volume                  53
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C42 H48 N6 Ni, 2(Cl O4), 3(C2 H6 O S)'
_chemical_formula_sum            'C48 H66 Cl2 N6 Ni O11 S3'
_chemical_formula_weight         1128.85
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      trigonal
_space_group_IT_number           155
_space_group_name_Hall           'R 3 2"'
_space_group_name_H-M_alt        'R 3 2 :H'
_symmetry_space_group_name_Hall  'R 3 2"'
_symmetry_space_group_name_H-M   'R 3 2 :H'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   14.7440(11)
_cell_length_b                   14.7440(11)
_cell_length_c                   42.978(3)
_cell_measurement_reflns_used    8979
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.71
_cell_measurement_theta_min      2.48
_cell_volume                     8091.1(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       55
_diffrn_reflns_limit_l_min       -55
_diffrn_reflns_number            24165
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.444
_diffrn_reflns_theta_min         1.664
_exptl_absorpt_coefficient_mu    0.637
_exptl_absorpt_correction_T_max  0.9195
_exptl_absorpt_correction_T_min  0.8241
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_description       prism
_exptl_crystal_F_000             3564
_exptl_crystal_size_max          0.359
_exptl_crystal_size_mid          0.343
_exptl_crystal_size_min          0.222
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.020(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0264
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0409P)²+4.8771P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0725
_refine_ls_wR_factor_ref         0.0739
_reflns_Friedel_coverage         0.791
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3892
_reflns_number_total             4138
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic4031766_si_002.cif
_cod_data_source_block           2
_cod_original_cell_volume        8091.0(14)
_cod_database_code               4337685
#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   0.804
_shelx_estimated_absorpt_t_max   0.872
_shelxl_version_number           2013-3
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z'
'x-y, -y, -z'
'-x, -x+y, -z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+1/3'
'x-y+2/3, -y+1/3, -z+1/3'
'-x+2/3, -x+y+1/3, -z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+2/3'
'x-y+1/3, -y+2/3, -z+2/3'
'-x+1/3, -x+y+2/3, -z+2/3'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.0000 0.0000 0.0000 0.01913(13) Uani 1 6 d S T P . .
N1 N 0.13955(13) 0.06086(16) 0.02659(4) 0.0242(4) Uani 1 1 d . . . . .
H1NA H 0.1654 0.1356 0.0312 0.029 Uiso 1 1 calc R U . . .
H1NB H 0.1243 0.0228 0.0466 0.029 Uiso 1 1 calc R U . . .
C1 C 0.22202(15) 0.05063(15) 0.00970(4) 0.0234(4) Uani 1 1 d . . . . .
H1 H 0.2581 0.1113 -0.0049 0.028 Uiso 1 1 calc R U . . .
C11 C 0.30367(19) 0.0517(2) 0.03140(5) 0.0318(5) Uani 1 1 d . . . . .
C12 C 0.40867(19) 0.1263(2) 0.02845(7) 0.0459(6) Uani 1 1 d . . . . .
H12 H 0.4311 0.1778 0.0126 0.055 Uiso 1 1 calc R U . . .
C13 C 0.4819(2) 0.1251(3) 0.04919(9) 0.0683(11) Uani 1 1 d . . . . .
H13 H 0.5537 0.1770 0.0475 0.082 Uiso 1 1 calc R U . . .
C14 C 0.4510(3) 0.0502(4) 0.07178(8) 0.0717(12) Uani 1 1 d . . . . .
H14 H 0.5013 0.0499 0.0855 0.086 Uiso 1 1 calc R U . . .
C15 C 0.3485(3) -0.0237(3) 0.07460(7) 0.0669(10) Uani 1 1 d . . . . .
H15 H 0.3273 -0.0761 0.0902 0.080 Uiso 1 1 calc R U . . .
C16 C 0.2745(2) -0.0233(3) 0.05478(5) 0.0470(6) Uani 1 1 d . . . . .
H16 H 0.2028 -0.0749 0.0572 0.056 Uiso 1 1 calc R U . . .
Ni2 Ni 0.0000 0.0000 0.5000 0.02187(14) Uani 1 6 d S T P . .
N2 N 0.08123(15) 0.14047(13) 0.47294(4) 0.0254(4) Uani 1 1 d . . . . .
H2NA H 0.0741 0.1231 0.4505 0.031 Uiso 1 1 calc R U . . .
H2NB H 0.0512 0.1863 0.4768 0.031 Uiso 1 1 calc R U . . .
C2 C 0.19351(15) 0.19509(15) 0.48209(4) 0.0232(4) Uani 1 1 d . . . . .
H2 H 0.2239 0.1518 0.4745 0.028 Uiso 1 1 calc R U . . .
C21 C 0.25771(16) 0.30368(18) 0.46801(5) 0.0257(4) Uani 1 1 d . . . . .
C22 C 0.25716(18) 0.39009(18) 0.48104(5) 0.0325(5) Uani 1 1 d . . . . .
H22 H 0.2165 0.3811 0.4991 0.039 Uiso 1 1 calc R U . . .
C23 C 0.31519(19) 0.48927(19) 0.46795(6) 0.0397(5) Uani 1 1 d . . . . .
H23 H 0.3135 0.5473 0.4769 0.048 Uiso 1 1 calc R U . . .
C24 C 0.3754(2) 0.5027(2) 0.44179(6) 0.0461(7) Uani 1 1 d . . . . .
H24 H 0.4153 0.5701 0.4327 0.055 Uiso 1 1 calc R U . . .
C25 C 0.3773(2) 0.4186(2) 0.42896(6) 0.0467(6) Uani 1 1 d . . . . .
H25 H 0.4189 0.4281 0.4110 0.056 Uiso 1 1 calc R U . . .
C26 C 0.31885(18) 0.3191(2) 0.44199(5) 0.0347(5) Uani 1 1 d . . . . .
H26 H 0.3211 0.2615 0.4329 0.042 Uiso 1 1 calc R U . . .
Cl1 Cl 0.0000 0.0000 0.10321(2) 0.0347(2) Uani 1 3 d S T P . .
O11 O 0.0000 0.0000 0.13654(6) 0.0514(8) Uani 1 3 d S T P . .
O12 O 0.0434(2) -0.0619(2) 0.09160(4) 0.0525(5) Uani 1 1 d . . . . .
Cl2 Cl 0.0000 0.0000 0.39535(2) 0.0445(2) Uani 1 3 d S T P . .
O21 O 0.0000 0.0000 0.36219(7) 0.0634(11) Uani 1 3 d S T P . .
O22 O 0.10444(17) 0.0574(3) 0.40720(5) 0.0743(7) Uani 1 1 d . . . . .
S1S S 0.39257(10) 0.36266(9) 0.01464(3) 0.0346(3) Uani 0.5 1 d . . P A -1
O1S O 0.2807(4) 0.2820(4) 0.00972(11) 0.062(2) Uani 0.5 1 d . . P A -1
C1S C 0.3980(14) 0.4851(9) 0.0178(4) 0.050(3) Uani 0.5 1 d . . P A -1
H1SA H 0.3571 0.4920 0.0009 0.060 Uiso 0.5 1 calc R U P A -1
H1SB H 0.4710 0.5417 0.0163 0.060 Uiso 0.5 1 calc R U P A -1
H1SC H 0.3689 0.4893 0.0379 0.060 Uiso 0.5 1 calc R U P A -1
C2S C 0.4538(10) 0.3842(14) -0.0228(4) 0.059(3) Uani 0.5 1 d . . P A -1
H2SA H 0.4604 0.3234 -0.0285 0.071 Uiso 0.5 1 calc R U P A -1
H2SB H 0.5235 0.4468 -0.0220 0.071 Uiso 0.5 1 calc R U P A -1
H2SC H 0.4110 0.3943 -0.0384 0.071 Uiso 0.5 1 calc R U P A -1
S2S S 0.03286(9) 0.38782(9) 0.48681(3) 0.0294(2) Uani 0.5 1 d . . P B -1
O2S O 0.0016(12) 0.2758(6) 0.49415(15) 0.0369(17) Uani 0.5 1 d . . P B -1
C3S C 0.0649(19) 0.4520(15) 0.5230(6) 0.050(4) Uani 0.5 1 d . . P B -1
H3SA H 0.0066 0.4141 0.5375 0.060 Uiso 0.5 1 calc R U P B -1
H3SB H 0.0780 0.5236 0.5204 0.060 Uiso 0.5 1 calc R U P B -1
H3SC H 0.1279 0.4542 0.5313 0.060 Uiso 0.5 1 calc R U P B -1
C4S C -0.0826(19) 0.393(2) 0.4790(6) 0.042(3) Uani 0.5 1 d . . P B -1
H4SA H -0.1137 0.3558 0.4594 0.050 Uiso 0.5 1 calc R U P B -1
H4SB H -0.0652 0.4659 0.4771 0.050 Uiso 0.5 1 calc R U P B -1
H4SC H -0.1326 0.3591 0.4960 0.050 Uiso 0.5 1 calc R U P B -1
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'
S S 0.1246 0.1234 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1 Ni1 N1 91.69(11) 6 2
N1 Ni1 N1 93.70(6) 6 5
N1 Ni1 N1 172.89(11) 2 5
N1 Ni1 N1 81.32(9) 6 3
N1 Ni1 N1 93.70(6) 2 3
N1 Ni1 N1 91.69(11) 5 3
N1 Ni1 N1 93.70(6) 6 4
N1 Ni1 N1 81.32(9) 2 4
N1 Ni1 N1 93.70(6) 5 4
N1 Ni1 N1 172.89(11) 3 4
N1 Ni1 N1 172.89(11) 6 .
N1 Ni1 N1 93.70(6) 2 .
N1 Ni1 N1 81.32(9) 5 .
N1 Ni1 N1 93.70(6) 3 .
N1 Ni1 N1 91.69(11) 4 .
C1 N1 Ni1 111.32(11) . .
N1 C1 C11 112.58(15) . .
N1 C1 C1 109.78(12) . 5
C11 C1 C1 109.95(15) . 5
C12 C11 C16 118.3(2) . .
C12 C11 C1 121.2(2) . .
C16 C11 C1 120.4(2) . .
C11 C12 C13 119.5(3) . .
C14 C13 C12 120.8(3) . .
C15 C14 C13 120.0(3) . .
C14 C15 C16 120.3(3) . .
C15 C16 C11 121.0(3) . .
N2 Ni2 N2 171.32(11) 4_556 2
N2 Ni2 N2 93.26(11) 4_556 3
N2 Ni2 N2 93.35(6) 2 3
N2 Ni2 N2 93.35(6) 4_556 6_556
N2 Ni2 N2 80.65(9) 2 6_556
N2 Ni2 N2 171.32(11) 3 6_556
N2 Ni2 N2 93.35(6) 4_556 5_556
N2 Ni2 N2 93.26(11) 2 5_556
N2 Ni2 N2 80.65(9) 3 5_556
N2 Ni2 N2 93.35(6) 6_556 5_556
N2 Ni2 N2 80.66(9) 4_556 .
N2 Ni2 N2 93.35(6) 2 .
N2 Ni2 N2 93.35(6) 3 .
N2 Ni2 N2 93.26(11) 6_556 .
N2 Ni2 N2 171.32(11) 5_556 .
C2 N2 Ni2 108.21(12) . .
N2 C2 C21 113.79(15) . .
N2 C2 C2 106.12(13) . 4_556
C21 C2 C2 114.07(13) . 4_556
C26 C21 C22 118.4(2) . .
C26 C21 C2 120.5(2) . .
C22 C21 C2 121.14(19) . .
C23 C22 C21 121.1(2) . .
C24 C23 C22 119.5(2) . .
C25 C24 C23 120.0(2) . .
C24 C25 C26 120.6(2) . .
C21 C26 C25 120.5(2) . .
O11 Cl1 O12 110.26(8) . 3
O11 Cl1 O12 110.26(8) . 2
O12 Cl1 O12 108.67(8) 3 2
O11 Cl1 O12 110.26(8) . .
O12 Cl1 O12 108.67(8) 3 .
O12 Cl1 O12 108.67(8) 2 .
O21 Cl2 O22 110.88(9) . 2
O21 Cl2 O22 110.88(9) . .
O22 Cl2 O22 108.03(9) 2 .
O21 Cl2 O22 110.88(9) . 3
O22 Cl2 O22 108.03(9) 2 3
O22 Cl2 O22 108.03(9) . 3
O1S S1S C1S 107.0(7) . .
O1S S1S C2S 105.8(5) . .
C1S S1S C2S 97.2(6) . .
O2S S2S C3S 104.9(8) . .
O2S S2S C4S 108.1(11) . .
C3S S2S C4S 98.7(8) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 N1 2.1210(16) .
Ni1 N1 2.1209(16) 2
Ni1 N1 2.1209(16) 3
Ni1 N1 2.1209(16) 4
Ni1 N1 2.1209(16) 5
Ni1 N1 2.1209(16) 6
N1 C1 1.487(2) .
C1 C11 1.516(3) .
C1 C1 1.539(4) 5
C11 C12 1.385(4) .
C11 C16 1.394(4) .
C12 C13 1.407(4) .
C13 C14 1.366(6) .
C14 C15 1.356(6) .
C15 C16 1.387(4) .
Ni2 N2 2.1438(17) .
Ni2 N2 2.1438(17) 2
Ni2 N2 2.1438(17) 3
Ni2 N2 2.1438(17) 4_556
Ni2 N2 2.1438(17) 5_556
Ni2 N2 2.1438(17) 6_556
N2 C2 1.487(3) .
C2 C21 1.520(3) .
C2 C2 1.540(4) 4_556
C21 C26 1.382(3) .
C21 C22 1.395(3) .
C22 C23 1.391(3) .
C23 C24 1.384(4) .
C24 C25 1.370(4) .
C25 C26 1.394(4) .
Cl1 O11 1.433(3) .
Cl1 O12 1.4411(19) 3
Cl1 O12 1.4411(19) 2
Cl1 O12 1.4411(19) .
Cl2 O21 1.425(3) .
Cl2 O22 1.430(2) 2
Cl2 O22 1.430(2) .
Cl2 O22 1.430(2) 3
S1S O1S 1.490(4) .
S1S C1S 1.772(14) .
S1S C2S 1.794(17) .
S2S O2S 1.509(5) .
S2S C3S 1.76(2) .
S2S C4S 1.77(2) .
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 H1NB O12 0.99 2.29 3.244(3) 162.3
N1 H1NA O1S 0.99 2.18 2.950(5) 134.0
N2 H2NA O22 0.99 2.24 3.165(3) 154.4
N2 H2NB O2S 0.99 1.95 2.922(6) 167.0
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
N1 Ni1 N1 C1 58.38(13) 6 .
N1 Ni1 N1 C1 -162.38(16) 2 .
N1 Ni1 N1 C1 12.51(10) 5 .
N1 Ni1 N1 C1 103.66(18) 3 .
N1 Ni1 N1 C1 -80.98(13) 4 .
Ni1 N1 C1 C11 -157.27(15) . .
Ni1 N1 C1 C1 -34.4(2) . 5
N1 C1 C11 C12 -121.4(2) . .
C1 C1 C11 C12 115.9(2) 5 .
N1 C1 C11 C16 59.1(3) . .
C1 C1 C11 C16 -63.7(3) 5 .
C16 C11 C12 C13 -0.9(3) . .
C1 C11 C12 C13 179.6(2) . .
C11 C12 C13 C14 1.2(4) . .
C12 C13 C14 C15 -0.5(5) . .
C13 C14 C15 C16 -0.5(5) . .
C14 C15 C16 C11 0.9(4) . .
C12 C11 C16 C15 -0.2(4) . .
C1 C11 C16 C15 179.4(2) . .
N2 Ni2 N2 C2 16.56(9) 4_556 .
N2 Ni2 N2 C2 -169.76(13) 2 .
N2 Ni2 N2 C2 -76.19(16) 3 .
N2 Ni2 N2 C2 109.43(13) 6_556 .
N2 Ni2 N2 C2 -30.18(12) 5_556 .
Ni2 N2 C2 C21 -171.87(14) . .
Ni2 N2 C2 C2 -45.61(19) . 4_556
N2 C2 C21 C26 -99.4(2) . .
C2 C2 C21 C26 138.7(2) 4_556 .
N2 C2 C21 C22 81.1(2) . .
C2 C2 C21 C22 -40.8(3) 4_556 .
C26 C21 C22 C23 1.1(3) . .
C2 C21 C22 C23 -179.39(19) . .
C21 C22 C23 C24 -0.7(4) . .
C22 C23 C24 C25 0.1(4) . .
C23 C24 C25 C26 0.2(4) . .
C22 C21 C26 C25 -0.8(3) . .
C2 C21 C26 C25 179.7(2) . .
C24 C25 C26 C21 0.2(4) . .
