#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:07:42 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180491 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/60/7216071.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_7216071
loop_
_publ_author_name
'Burrows, Andrew D.'
'Harrington, Ross W.'
'Mahon, Mary F.'
'Teat, Simon J.'
_publ_section_title
;
 The structural influence of ligand coordination and hydrogen bonding
 capabilities in the crystal engineering of metal thiosemicarbazide
 compounds with malonate
;
_journal_issue                   64
_journal_name_full               CrystEngComm
_journal_page_first              388
_journal_paper_doi               10.1039/b505655a
_journal_volume                  7
_journal_year                    2005
_chemical_formula_moiety         'C12 H34 N10 Ni O9 S3'
_chemical_formula_sum            'C12 H34 N10 Ni O9 S3'
_chemical_formula_weight         617.38
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.868(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.711(2)
_cell_length_b                   10.2151(15)
_cell_length_c                   18.702(3)
_cell_measurement_reflns_used    34278
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.65
_cell_measurement_theta_min      2.28
_cell_volume                     2600.6(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device_type  'Bruker SMART 1K CCD diffractometer'
_diffrn_measurement_method       'thin-slice ω scans'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_source         'Daresbury SRS station 9.8'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.69410
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            33308
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.27
_diffrn_reflns_theta_min         2.22
_diffrn_standards_decay_%        20
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.048
_exptl_absorpt_correction_T_max  0.9793
_exptl_absorpt_correction_T_min  0.8338
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         7138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0319P)²+1.1527P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0742
_refine_ls_wR_factor_ref         0.0763
_reflns_number_gt                6145
_reflns_number_total             7138
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b505655a.txt
_cod_data_source_block           3
_cod_original_cell_volume        2600.5(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7216071
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
Ni1 Ni 0.246421(14) 0.265340(19) 0.167514(10) 0.01702(6) Uani 1 1 d .
S1 S 0.33235(3) 0.22359(4) 0.06633(2) 0.02297(8) Uani 1 1 d .
S2 S 0.34229(3) 0.11340(4) 0.24511(2) 0.02206(8) Uani 1 1 d .
S3 S 0.34939(3) 0.44753(4) 0.20511(2) 0.02278(9) Uani 1 1 d .
N1 N 0.14794(10) 0.12274(13) 0.11828(7) 0.0195(2) Uani 1 1 d .
H1A H 0.0853(15) 0.149(2) 0.1104(11) 0.024(5) Uiso 1 1 d .
H1B H 0.1482(16) 0.055(2) 0.1475(13) 0.037(6) Uiso 1 1 d .
N2 N 0.17076(12) 0.07757(16) 0.05099(9) 0.0320(3) Uani 1 1 d .
H2 H 0.1366(17) 0.017(2) 0.0306(13) 0.042(6) Uiso 1 1 d .
N3 N 0.26384(12) 0.06164(18) -0.03973(9) 0.0341(4) Uani 1 1 d .
H3 H 0.2169(17) 0.009(2) -0.0584(13) 0.039(6) Uiso 1 1 d .
N4 N 0.16307(10) 0.27825(13) 0.25420(7) 0.0193(2) Uani 1 1 d .
H4A H 0.1031(17) 0.256(2) 0.2416(12) 0.026(5) Uiso 1 1 d .
H4B H 0.1623(15) 0.354(2) 0.2704(11) 0.026(5) Uiso 1 1 d .
N5 N 0.19638(11) 0.19975(14) 0.31439(8) 0.0242(3) Uani 1 1 d .
H5 H 0.1623(15) 0.200(2) 0.3470(12) 0.024(5) Uiso 1 1 d .
N6 N 0.29860(11) 0.05668(16) 0.37672(8) 0.0286(3) Uani 1 1 d .
H6 H 0.2590(16) 0.062(2) 0.4079(12) 0.031(6) Uiso 1 1 d .
N7 N 0.15447(10) 0.41392(13) 0.11667(8) 0.0219(3) Uani 1 1 d .
H7A H 0.0944(16) 0.405(2) 0.1269(11) 0.028(5) Uiso 1 1 d .
H7B H 0.1562(18) 0.406(3) 0.0696(15) 0.051(7) Uiso 1 1 d .
N8 N 0.18320(11) 0.54375(14) 0.13508(8) 0.0270(3) Uani 1 1 d .
H8 H 0.1574(17) 0.603(2) 0.1065(13) 0.041(6) Uiso 1 1 d .
N9 N 0.29534(12) 0.69427(15) 0.17804(10) 0.0325(3) Uani 1 1 d .
H9 H 0.2512(18) 0.745(2) 0.1635(13) 0.043(7) Uiso 1 1 d .
N10 N -0.08129(11) 0.22718(14) 0.00954(8) 0.0261(3) Uani 1 1 d .
O1 O 0.14846(9) 0.52933(11) 0.32978(7) 0.0284(3) Uani 1 1 d .
O1W O 0.04340(12) 0.31591(16) 0.39117(8) 0.0372(3) Uani 1 1 d .
H1WA H -0.016(3) 0.314(3) 0.3735(17) 0.069(10) Uiso 1 1 d .
H1WB H 0.079(4) 0.386(6) 0.382(3) 0.20(3) Uiso 1 1 d .
O2 O 0.01960(9) 0.63247(11) 0.27140(7) 0.0279(3) Uani 1 1 d .
O2W O -0.13084(11) 0.57762(17) 0.04292(8) 0.0352(3) Uani 1 1 d .
H2WA H -0.099(2) 0.506(3) 0.0450(15) 0.055(8) Uiso 1 1 d .
H2WB H -0.090(2) 0.637(3) 0.0519(15) 0.057(8) Uiso 1 1 d .
O3 O 0.04256(9) 0.93327(12) 0.29693(7) 0.0263(2) Uani 1 1 d .
H3O H 0.018(2) 1.001(3) 0.2666(17) 0.073(9) Uiso 1 1 d .
O4 O 0.13273(9) 0.88229(12) 0.20914(7) 0.0279(3) Uani 1 1 d .
O5 O -0.14916(13) 0.23345(16) -0.03990(11) 0.0578(5) Uani 1 1 d .
O6 O -0.03445(11) 0.32747(15) 0.03152(9) 0.0456(4) Uani 1 1 d .
O7 O -0.05900(10) 0.12026(13) 0.03775(7) 0.0324(3) Uani 1 1 d .
C1 C 0.25220(11) 0.11457(16) 0.02376(9) 0.0219(3) Uani 1 1 d .
C2 C 0.35149(13) 0.07061(18) -0.07633(9) 0.0280(3) Uani 1 1 d .
H2A H 0.3972 0.1357 -0.0515 0.034 Uiso 1 1 calc R
H2B H 0.3331 0.1008 -0.1264 0.034 Uiso 1 1 calc R
C3 C 0.40192(16) -0.0598(2) -0.07705(14) 0.0453(5) Uani 1 1 d .
H3A H 0.4227 -0.0879 -0.0275 0.068 Uiso 1 1 calc R
H3B H 0.4596 -0.0522 -0.1031 0.068 Uiso 1 1 calc R
H3C H 0.3564 -0.1245 -0.1010 0.068 Uiso 1 1 calc R
C4 C 0.27607(11) 0.12396(15) 0.31582(8) 0.0205(3) Uani 1 1 d .
C5 C 0.38505(14) -0.02588(19) 0.39286(10) 0.0329(4) Uani 1 1 d .
H5A H 0.4452 0.0265 0.3899 0.040 Uiso 1 1 calc R
H5B H 0.3835 -0.0977 0.3572 0.040 Uiso 1 1 calc R
C6 C 0.38664(16) -0.0822(2) 0.46754(11) 0.0383(4) Uani 1 1 d .
H6A H 0.3875 -0.0107 0.5026 0.057 Uiso 1 1 calc R
H6B H 0.4455 -0.1363 0.4787 0.057 Uiso 1 1 calc R
H6C H 0.3280 -0.1361 0.4698 0.057 Uiso 1 1 calc R
C7 C 0.27357(12) 0.56786(15) 0.17018(9) 0.0213(3) Uani 1 1 d .
C8 C 0.39011(14) 0.74820(17) 0.20725(10) 0.0303(4) Uani 1 1 d .
H8A H 0.4322 0.6771 0.2297 0.036 Uiso 1 1 calc R
H8B H 0.3804 0.8130 0.2451 0.036 Uiso 1 1 calc R
C9 C 0.44054(17) 0.8126(3) 0.14998(12) 0.0478(5) Uani 1 1 d .
H9A H 0.4566 0.7467 0.1152 0.072 Uiso 1 1 calc R
H9B H 0.5011 0.8546 0.1720 0.072 Uiso 1 1 calc R
H9C H 0.3970 0.8788 0.1253 0.072 Uiso 1 1 calc R
C10 C 0.10507(12) 0.62949(15) 0.30593(8) 0.0199(3) Uani 1 1 d .
C11 C 0.15736(12) 0.76052(15) 0.31859(9) 0.0219(3) Uani 1 1 d .
H11A H 0.1561 0.7872 0.3694 0.026 Uiso 1 1 calc R
H11B H 0.2269 0.7506 0.3102 0.026 Uiso 1 1 calc R
C12 C 0.11017(11) 0.86569(15) 0.26982(9) 0.0211(3) 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'
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
N4 Ni1 N1 90.07(5)
N4 Ni1 N7 87.25(6)
N1 Ni1 N7 89.05(5)
N4 Ni1 S1 172.70(4)
N1 Ni1 S1 83.22(4)
N7 Ni1 S1 95.49(4)
N4 Ni1 S3 94.65(4)
N1 Ni1 S3 170.30(4)
N7 Ni1 S3 82.73(4)
S1 Ni1 S3 92.417(17)
N4 Ni1 S2 83.29(4)
N1 Ni1 S2 95.30(4)
N7 Ni1 S2 169.58(4)
S1 Ni1 S2 94.425(18)
S3 Ni1 S2 93.670(19)
C1 S1 Ni1 97.83(6)
C4 S2 Ni1 97.16(6)
C7 S3 Ni1 97.95(6)
N2 N1 Ni1 114.50(10)
C1 N2 N1 122.16(14)
C1 N3 C2 125.99(15)
N5 N4 Ni1 115.23(10)
C4 N5 N4 122.03(14)
C4 N6 C5 125.08(15)
N8 N7 Ni1 115.34(10)
C7 N8 N7 120.05(14)
C7 N9 C8 125.97(16)
O5 N10 O7 119.49(15)
O5 N10 O6 121.03(16)
O7 N10 O6 119.49(15)
N3 C1 N2 114.82(15)
N3 C1 S1 123.07(13)
N2 C1 S1 122.09(13)
N3 C2 C3 110.81(16)
N6 C4 N5 114.89(15)
N6 C4 S2 122.83(13)
N5 C4 S2 122.28(12)
N6 C5 C6 109.51(16)
N9 C7 N8 114.25(15)
N9 C7 S3 122.96(13)
N8 C7 S3 122.70(12)
N9 C8 C9 111.48(16)
O1 C10 O2 125.26(15)
O1 C10 C11 118.21(14)
O2 C10 C11 116.53(13)
C12 C11 C10 111.90(13)
O4 C12 O3 123.84(15)
O4 C12 C11 121.55(15)
O3 C12 C11 114.58(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ni1 N4 2.0963(14)
Ni1 N1 2.1203(13)
Ni1 N7 2.1237(14)
Ni1 S1 2.3841(5)
Ni1 S3 2.3903(5)
Ni1 S2 2.4055(5)
S1 C1 1.6949(16)
S2 C4 1.6948(17)
S3 C7 1.6900(16)
N1 N2 1.410(2)
N2 C1 1.336(2)
N3 C1 1.331(2)
N3 C2 1.455(2)
N4 N5 1.4127(18)
N5 C4 1.337(2)
N6 C4 1.334(2)
N6 C5 1.457(2)
N7 N8 1.4143(19)
N8 C7 1.354(2)
N9 C7 1.330(2)
N9 C8 1.456(2)
N10 O5 1.233(2)
N10 O7 1.2353(19)
N10 O6 1.2522(19)
O1 C10 1.2394(18)
O2 C10 1.2690(19)
O3 C12 1.306(2)
O4 C12 1.223(2)
C2 C3 1.502(3)
C5 C6 1.508(3)
C8 C9 1.495(3)
C10 C11 1.524(2)
C11 C12 1.504(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
_geom_hbond_site_symmetry_A
N1 H1A O7 0.89(2) 2.28(2) 3.0492(19) 143.9(17) .
N1 H1B O4 0.88(2) 2.13(2) 3.0082(18) 173(2) 1_545
N2 H2 O7 0.84(2) 2.10(3) 2.929(2) 170(2) 3
N3 H3 O1 0.88(2) 2.22(2) 2.898(2) 133(2) 4_565
N3 H3 O7 0.88(2) 2.60(2) 3.371(2) 147(2) 3
N4 H4A O2 0.86(2) 2.09(2) 2.9038(19) 157.0(19) 2_545
N4 H4B O1 0.83(2) 2.13(2) 2.9470(18) 168(2) .
N5 H5 O1W 0.81(2) 2.25(2) 2.931(2) 141.6(19) .
N4 H4A O2 0.86(2) 2.09(2) 2.9038(19) 157.0(19) 2_545
N5 H5 O2W 0.81(2) 2.49(2) 3.172(2) 142.5(19) 2_545
N6 H6 O2W 0.84(2) 2.09(2) 2.902(2) 163(2) 2_545
N7 H7A O3 0.87(2) 2.51(2) 3.315(2) 154.8(19) 2_545
N7 H7A O6 0.87(2) 2.49(2) 3.006(2) 118.9(17) .
N7 H7B O2W 0.89(3) 2.10(3) 2.965(2) 165(2) 3_565
N8 H8 O5 0.86(3) 2.08(3) 2.893(2) 159(2) 3_565
N9 H9 O4 0.82(3) 2.38(3) 3.051(2) 140(2) .
N9 H9 O5 0.82(3) 2.56(2) 3.162(2) 131(2) 3_565
O1W H1WA O4 0.84(3) 2.20(3) 2.954(2) 149(3) 2_545
O1W H1WA O5 0.84(3) 2.63(3) 3.115(3) 118(3) 4_566
O3 H3O O2 0.93(3) 1.58(3) 2.4980(17) 169(3) 2
O2W H2WA O6 0.85(3) 2.06(3) 2.896(2) 170(3) .
O2W H2WB O1W 0.82(3) 2.18(3) 2.920(2) 150(3) 2
O2W H2WB O6 0.82(3) 2.48(3) 2.961(2) 119(2) 3_565
O1W H1WB O1 0.89(6) 2.05(6) 2.923(2) 163(6) .
