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#$Date: 2016-03-26 22:07:42 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180491 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/60/7216079.cif $
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#
# 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_7216079
loop_
_publ_author_name
'Hallale, Oren'
'Bourne, Susan A.'
'Koch, Klaus R.'
_publ_section_title
;
 Metallamacrocyclic complexes of Ni(ii) with
 3,3,3?,3?-tetraalkyl-1,1?-aroylbis(thioureas): crystal and molecular
 structures of a 2 : 2 metallamacrocycle and a pyridine adduct of the
 analogous 3 : 3 complex
;
_journal_issue                   25
_journal_name_full               CrystEngComm
_journal_page_first              161
_journal_paper_doi               10.1039/b419468c
_journal_volume                  7
_journal_year                    2005
_chemical_formula_sum            'C18 H24 N4 Ni O2 S2'
_chemical_formula_weight         451.24
_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                81.0900(10)
_cell_angle_beta                 82.7990(10)
_cell_angle_gamma                84.6010(10)
_cell_formula_units_Z            2
_cell_length_a                   8.32370(10)
_cell_length_b                   9.61490(10)
_cell_length_c                   12.87170(10)
_cell_measurement_temperature    173(2)
_cell_volume                     1006.749(18)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0147
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8648
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.61
_exptl_absorpt_coefficient_mu    1.192
_exptl_absorpt_correction_T_max  0.8415
_exptl_absorpt_correction_T_min  0.7163
_exptl_absorpt_correction_type   semi-empirical
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.773
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4625
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.773
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0246
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0924
_reflns_number_gt                4139
_reflns_number_total             4625
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b419468c.txt
_cod_data_source_block           1
_cod_original_cell_volume        1006.750(18)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7216079
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 0.701571(19) 0.764716(17) 0.681616(12) 0.01655(8) Uani 1 1 d .
O1A O 0.87850(12) 0.86367(11) 0.69868(8) 0.0213(2) Uani 1 1 d .
C2A C 0.95793(16) 0.85816(14) 0.77796(11) 0.0174(3) Uani 1 1 d .
N3A N 0.92372(15) 0.80241(13) 0.87743(9) 0.0219(3) Uani 1 1 d .
S4A S 0.65601(5) 0.67383(4) 0.84403(3) 0.02461(11) Uani 1 1 d .
N4A N 0.77404(15) 0.69145(13) 1.02080(9) 0.0228(3) Uani 1 1 d .
C4A C 0.79501(17) 0.72806(15) 0.91535(11) 0.0191(3) Uani 1 1 d .
C11A C 1.11617(16) 0.92612(14) 0.75590(11) 0.0172(3) Uani 1 1 d .
C12A C 1.21869(18) 0.91168(15) 0.83608(11) 0.0206(3) Uani 1 1 d .
H15 H 1.1857 0.8624 0.9041 0.025 Uiso 1 1 calc R
C13A C 1.36804(18) 0.96912(15) 0.81632(11) 0.0223(3) Uani 1 1 d .
H3 H 1.4367 0.9601 0.8710 0.027 Uiso 1 1 calc R
C16A C 1.16480(16) 0.99907(14) 0.65667(11) 0.0174(3) Uani 1 1 d .
H4 H 1.0953 1.0096 0.6024 0.021 Uiso 1 1 calc R
C41A C 0.88478(19) 0.73483(17) 1.08870(11) 0.0248(3) Uani 1 1 d .
H5A H 0.8246 0.7469 1.1585 0.030 Uiso 1 1 calc R
H5B H 0.9256 0.8268 1.0560 0.030 Uiso 1 1 calc R
C42A C 1.0276(2) 0.6258(2) 1.10393(14) 0.0367(4) Uani 1 1 d .
H13A H 0.9873 0.5339 1.1340 0.055 Uiso 1 1 calc R
H13B H 1.0961 0.6548 1.1522 0.055 Uiso 1 1 calc R
H13C H 1.0916 0.6185 1.0354 0.055 Uiso 1 1 calc R
C43A C 0.64425(18) 0.60462(16) 1.07545(11) 0.0249(3) Uani 1 1 d .
H7A H 0.6809 0.5502 1.1412 0.030 Uiso 1 1 calc R
H7B H 0.6225 0.5364 1.0296 0.030 Uiso 1 1 calc R
C44A C 0.4882(2) 0.69359(19) 1.10303(14) 0.0368(4) Uani 1 1 d .
H18A H 0.5094 0.7618 1.1479 0.055 Uiso 1 1 calc R
H18B H 0.4059 0.6321 1.1410 0.055 Uiso 1 1 calc R
H18C H 0.4487 0.7441 1.0379 0.055 Uiso 1 1 calc R
O1B O 0.72862(12) 0.84931(11) 0.53929(7) 0.0193(2) Uani 1 1 d .
C2B C 0.62827(16) 0.86443(14) 0.47027(10) 0.0166(3) Uani 1 1 d .
N3B N 0.48080(14) 0.82240(12) 0.47733(9) 0.0178(2) Uani 1 1 d .
S4B S 0.51194(5) 0.63718(4) 0.66044(3) 0.02386(11) Uani 1 1 d .
N4B N 0.26049(14) 0.70446(12) 0.55139(9) 0.0180(2) Uani 1 1 d .
C4B C 0.41470(16) 0.73009(14) 0.55657(10) 0.0168(3) Uani 1 1 d .
C11B C 0.68425(16) 0.94285(14) 0.36373(10) 0.0165(3) Uani 1 1 d .
C12B C 0.58263(17) 0.96019(15) 0.28324(11) 0.0200(3) Uani 1 1 d .
H2 H 0.4789 0.9232 0.2969 0.024 Uiso 1 1 calc R
C41B C 0.17208(17) 0.78023(16) 0.46400(11) 0.0223(3) Uani 1 1 d .
H12A H 0.2062 0.8778 0.4464 0.027 Uiso 1 1 calc R
H12B H 0.0543 0.7861 0.4882 0.027 Uiso 1 1 calc R
C42B C 0.2014(2) 0.70968(19) 0.36489(13) 0.0354(4) Uani 1 1 d .
H17A H 0.3180 0.7024 0.3409 0.053 Uiso 1 1 calc R
H17B H 0.1433 0.7661 0.3091 0.053 Uiso 1 1 calc R
H17C H 0.1619 0.6150 0.3806 0.053 Uiso 1 1 calc R
C43B C 0.17418(17) 0.60013(15) 0.62888(11) 0.0215(3) Uani 1 1 d .
H14A H 0.0558 0.6235 0.6288 0.026 Uiso 1 1 calc R
H14B H 0.2021 0.6071 0.7003 0.026 Uiso 1 1 calc R
C44B C 0.2141(2) 0.44892(17) 0.60716(14) 0.0334(4) Uani 1 1 d .
H16A H 0.1899 0.4416 0.5357 0.050 Uiso 1 1 calc R
H16B H 0.1485 0.3855 0.6590 0.050 Uiso 1 1 calc R
H16C H 0.3296 0.4222 0.6127 0.050 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'
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'
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
O1A Ni1 O1B 85.75(4) . .
O1A Ni1 S4A 96.17(3) . .
O1B Ni1 S4A 176.55(3) . .
O1A Ni1 S4B 175.52(3) . .
O1B Ni1 S4B 94.70(3) . .
S4A Ni1 S4B 83.608(15) . .
C2A O1A Ni1 130.42(9) . .
O1A C2A N3A 130.45(13) . .
O1A C2A C11A 115.72(12) . .
N3A C2A C11A 113.83(12) . .
C2A N3A C4A 125.04(13) . .
C4A S4A Ni1 109.21(5) . .
C4A N4A C43A 123.02(12) . .
C4A N4A C41A 120.99(12) . .
C43A N4A C41A 115.98(12) . .
N4A C4A N3A 115.60(13) . .
N4A C4A S4A 116.95(11) . .
N3A C4A S4A 127.45(11) . .
C16A C11A C12A 119.62(13) . .
C16A C11A C2A 121.18(12) . .
C12A C11A C2A 119.17(12) . .
C13A C12A C11A 120.17(13) . .
C12A C13A C12B 120.08(13) . 2_776
C11A C16A C11B 120.41(13) . 2_776
N4A C41A C42A 111.16(13) . .
N4A C43A C44A 112.05(13) . .
C2B O1B Ni1 128.96(9) . .
O1B C2B N3B 130.23(13) . .
O1B C2B C11B 116.09(12) . .
N3B C2B C11B 113.68(12) . .
C2B N3B C4B 124.89(12) . .
C4B S4B Ni1 105.77(5) . .
C4B N4B C43B 122.45(12) . .
C4B N4B C41B 119.97(11) . .
C43B N4B C41B 117.57(11) . .
N4B C4B N3B 115.94(12) . .
N4B C4B S4B 117.74(10) . .
N3B C4B S4B 126.26(10) . .
C16A C11B C12B 119.13(12) 2_776 .
C16A C11B C2B 121.53(12) 2_776 .
C12B C11B C2B 119.33(12) . .
C13A C12B C11B 120.56(13) 2_776 .
N4B C41B C42B 113.12(12) . .
N4B C43B C44B 113.54(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 O1A 1.8793(10) .
Ni1 O1B 1.8809(9) .
Ni1 S4A 2.1390(4) .
Ni1 S4B 2.1552(4) .
O1A C2A 1.2756(17) .
C2A N3A 1.3163(18) .
C2A C11A 1.5011(18) .
N3A C4A 1.3424(18) .
S4A C4A 1.7266(15) .
N4A C4A 1.3420(18) .
N4A C43A 1.4684(17) .
N4A C41A 1.4748(19) .
C11A C16A 1.3904(19) .
C11A C12A 1.4024(19) .
C12A C13A 1.386(2) .
C13A C12B 1.387(2) 2_776
C16A C11B 1.4012(19) 2_776
C41A C42A 1.520(2) .
C43A C44A 1.521(2) .
O1B C2B 1.2773(17) .
C2B N3B 1.3161(18) .
C2B C11B 1.5006(18) .
N3B C4B 1.3422(18) .
S4B C4B 1.7338(14) .
N4B C4B 1.3413(17) .
N4B C43B 1.4708(17) .
N4B C41B 1.4800(17) .
C11B C16A 1.4012(19) 2_776
C11B C12B 1.3987(19) .
C12B C13A 1.387(2) 2_776
C41B C42B 1.519(2) .
C43B C44B 1.521(2) .
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
O1B Ni1 O1A C2A -173.24(13) . .
S4A Ni1 O1A C2A 9.63(13) . .
S4B Ni1 O1A C2A -77.3(4) . .
Ni1 O1A C2A N3A -14.1(2) . .
Ni1 O1A C2A C11A 166.07(9) . .
O1A C2A N3A C4A 4.8(2) . .
C11A C2A N3A C4A -175.46(13) . .
O1A Ni1 S4A C4A -0.21(6) . .
O1B Ni1 S4A C4A -124.0(5) . .
S4B Ni1 S4A C4A 175.29(6) . .
C43A N4A C4A N3A -177.12(12) . .
C41A N4A C4A N3A 1.5(2) . .
C43A N4A C4A S4A 2.40(19) . .
C41A N4A C4A S4A -178.97(11) . .
C2A N3A C4A N4A -174.12(14) . .
C2A N3A C4A S4A 6.4(2) . .
Ni1 S4A C4A N4A 173.81(10) . .
Ni1 S4A C4A N3A -6.74(15) . .
O1A C2A C11A C16A 4.63(19) . .
N3A C2A C11A C16A -175.18(12) . .
O1A C2A C11A C12A -173.33(13) . .
N3A C2A C11A C12A 6.85(19) . .
C16A C11A C12A C13A -0.4(2) . .
C2A C11A C12A C13A 177.63(13) . .
C11A C12A C13A C12B -0.7(2) . 2_776
C12A C11A C16A C11B 0.5(2) . 2_776
C2A C11A C16A C11B -177.51(12) . 2_776
C4A N4A C41A C42A -89.75(17) . .
C43A N4A C41A C42A 88.97(16) . .
C4A N4A C43A C44A -88.21(18) . .
C41A N4A C43A C44A 93.09(16) . .
O1A Ni1 O1B C2B -161.60(12) . .
S4A Ni1 O1B C2B -37.5(6) . .
S4B Ni1 O1B C2B 22.87(12) . .
Ni1 O1B C2B N3B -2.2(2) . .
Ni1 O1B C2B C11B 177.43(8) . .
O1B C2B N3B C4B -12.7(2) . .
C11B C2B N3B C4B 167.60(12) . .
O1A Ni1 S4B C4B -124.1(4) . .
O1B Ni1 S4B C4B -28.47(6) . .
S4A Ni1 S4B C4B 148.51(5) . .
C43B N4B C4B N3B 176.49(11) . .
C41B N4B C4B N3B -2.16(18) . .
C43B N4B C4B S4B -0.99(17) . .
C41B N4B C4B S4B -179.64(9) . .
C2B N3B C4B N4B 177.71(12) . .
C2B N3B C4B S4B -5.1(2) . .
Ni1 S4B C4B N4B -155.79(9) . .
Ni1 S4B C4B N3B 27.02(13) . .
O1B C2B C11B C16A -2.63(19) . 2_776
N3B C2B C11B C16A 177.07(12) . 2_776
O1B C2B C11B C12B 178.28(12) . .
N3B C2B C11B C12B -2.01(18) . .
C16A C11B C12B C13A 1.6(2) 2_776 2_776
C2B C11B C12B C13A -179.30(12) . 2_776
C4B N4B C41B C42B 85.57(16) . .
C43B N4B C41B C42B -93.14(15) . .
C4B N4B C43B C44B -80.86(17) . .
C41B N4B C43B C44B 97.82(15) . .
