#------------------------------------------------------------------------------
#$Date: 2016-03-23 14:43:16 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179303 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/00/4320026.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_4320026
loop_
_publ_author_name
'Markus Tesmer'
'Mouhai Shu'
'Heinrich Vahrenkamp'
_publ_section_title
;
 Sulfur-Rich Zinc Chemistry: New Tris(thioimidazolyl)hydroborate Ligands
 and Their Zinc Complex Chemistry Related to the Structure and Function of
 Alcohol Dehydrogenase
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              4022
_journal_page_last               4029
_journal_paper_doi               10.1021/ic0101275
_journal_volume                  40
_journal_year                    2001
_chemical_formula_sum            'C25 H46 B Cl N6 O6 S3 Zn'
_chemical_formula_weight         734.49
_chemical_name_systematic
'[{Tris(tert-butyl-thioimidazolyl)borato}zinc-perchlorate]-bis-ethanol'
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 126.968(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.342(2)
_cell_length_b                   19.6274(16)
_cell_length_c                   18.5123(14)
_cell_measurement_temperature    293(2)
_cell_volume                     7356.9(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16169
_diffrn_reflns_theta_full        23.28
_diffrn_reflns_theta_max         23.28
_diffrn_reflns_theta_min         1.44
_exptl_absorpt_coefficient_mu    0.954
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3088
_refine_diff_density_max         0.979
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     429
_refine_ls_number_reflns         5296
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0402
_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)+(0.0661P)²+8.1541P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1145
_reflns_number_gt                4046
_reflns_number_total             5296
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic0101275_6.cif
_cod_data_source_block           mt9(complex6)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        7356.8(10)
_cod_database_code               4320026
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.20427(2) 0.96219(2) -0.00334(3) 0.03400(16) Uani 1 1 d . B .
S1 S 0.30146(5) 0.89964(5) 0.07922(6) 0.0329(2) Uani 1 1 d . . .
S2 S 0.22382(5) 1.07486(5) 0.04547(6) 0.0327(2) Uani 1 1 d . . .
S3 S 0.16019(5) 0.95786(5) -0.15558(7) 0.0392(3) Uani 1 1 d . . .
O3 O -0.00080(15) 0.67777(16) 0.11592(19) 0.0524(8) Uani 1 1 d . . .
O4 O 0.0759(2) 0.7452(2) 0.1178(3) 0.1032(16) Uani 1 1 d . . .
O5 O 0.03710(16) 0.64763(16) 0.0321(2) 0.0582(9) Uani 1 1 d . . .
O6 O -0.0323(3) 0.7386(3) -0.0121(3) 0.128(2) Uani 1 1 d . . .
B1 B 0.3143(2) 1.0330(2) -0.0308(3) 0.0296(10) Uani 1 1 d . . .
H1A H 0.3464 1.0535 -0.0376 0.035 Uiso 1 1 calc R . .
Cl1 Cl 0.01895(6) 0.70183(5) 0.06279(7) 0.0441(3) Uani 1 1 d . . .
N1 N 0.35182(14) 1.02122(14) 0.07192(19) 0.0258(7) Uani 1 1 d . . .
N2 N 0.39393(15) 0.98974(15) 0.21082(19) 0.0288(7) Uani 1 1 d . . .
N3 N 0.25734(15) 1.08599(15) -0.07000(19) 0.0280(7) Uani 1 1 d . . .
N4 N 0.17808(14) 1.15587(14) -0.10382(19) 0.0275(7) Uani 1 1 d . . .
N5 N 0.29113(15) 0.96541(15) -0.08653(19) 0.0287(7) Uani 1 1 d . . .
N6 N 0.23981(17) 0.87896(15) -0.1781(2) 0.0341(8) Uani 1 1 d . . .
C1 C 0.35076(18) 0.97161(18) 0.1219(2) 0.0273(8) Uani 1 1 d . . .
C2 C 0.39565(18) 1.07103(18) 0.1310(2) 0.0314(9) Uani 1 1 d . . .
H2A H 0.4060 1.1108 0.1147 0.038 Uiso 1 1 calc R . .
C3 C 0.42061(19) 1.05220(19) 0.2155(2) 0.0329(9) Uani 1 1 d . . .
H3 H 0.4505 1.0769 0.2679 0.040 Uiso 1 1 calc R . .
C4 C 0.4125(2) 0.94836(19) 0.2917(2) 0.0335(9) Uani 1 1 d . . .
C5 C 0.3516(2) 0.9367(2) 0.2882(3) 0.0496(12) Uani 1 1 d . . .
H5A H 0.3304 0.9795 0.2801 0.074 Uiso 1 1 calc R . .
H5B H 0.3646 0.9162 0.3438 0.074 Uiso 1 1 calc R . .
H5C H 0.3216 0.9070 0.2387 0.074 Uiso 1 1 calc R . .
C6 C 0.4435(2) 0.8818(2) 0.2929(3) 0.0454(11) Uani 1 1 d . . .
H6A H 0.4130 0.8575 0.2376 0.068 Uiso 1 1 calc R . .
H6B H 0.4540 0.8546 0.3431 0.068 Uiso 1 1 calc R . .
H6C H 0.4831 0.8911 0.2988 0.068 Uiso 1 1 calc R . .
C7 C 0.4636(2) 0.9886(2) 0.3774(3) 0.0479(11) Uani 1 1 d . . .
H7A H 0.5028 0.9947 0.3812 0.072 Uiso 1 1 calc R . .
H7B H 0.4744 0.9640 0.4295 0.072 Uiso 1 1 calc R . .
H7C H 0.4457 1.0323 0.3753 0.072 Uiso 1 1 calc R . .
C8 C 0.21982(18) 1.10676(18) -0.0451(2) 0.0277(8) Uani 1 1 d . . .
C9 C 0.23794(19) 1.12211(19) -0.1466(2) 0.0331(9) Uani 1 1 d . . .
H9 H 0.2557 1.1176 -0.1780 0.040 Uiso 1 1 calc R . .
C10 C 0.18926(19) 1.16466(19) -0.1677(2) 0.0329(9) Uani 1 1 d . . .
H10 H 0.1670 1.1946 -0.2164 0.040 Uiso 1 1 calc R . .
C11 C 0.12771(18) 1.19573(19) -0.1019(2) 0.0322(9) Uani 1 1 d . . .
C12 C 0.1640(2) 1.2364(2) -0.0138(3) 0.0414(10) Uani 1 1 d . . .
H12A H 0.1883 1.2058 0.0367 0.062 Uiso 1 1 calc R . .
H12B H 0.1326 1.2612 -0.0111 0.062 Uiso 1 1 calc R . .
H12C H 0.1941 1.2678 -0.0115 0.062 Uiso 1 1 calc R . .
C13 C 0.0932(2) 1.2457(2) -0.1815(3) 0.0401(10) Uani 1 1 d . . .
H13A H 0.1253 1.2760 -0.1756 0.060 Uiso 1 1 calc R . .
H13B H 0.0610 1.2716 -0.1816 0.060 Uiso 1 1 calc R . .
H13C H 0.0717 1.2208 -0.2371 0.060 Uiso 1 1 calc R . .
C14 C 0.0769(2) 1.1476(2) -0.1121(3) 0.0437(10) Uani 1 1 d . . .
H14A H 0.0578 1.1208 -0.1658 0.065 Uiso 1 1 calc R . .
H14B H 0.0429 1.1735 -0.1165 0.065 Uiso 1 1 calc R . .
H14C H 0.0978 1.1181 -0.0605 0.065 Uiso 1 1 calc R . .
C15 C 0.2318(2) 0.93389(19) -0.1403(2) 0.0318(9) Uani 1 1 d . . .
C16 C 0.3361(2) 0.92870(19) -0.0892(2) 0.0337(9) Uani 1 1 d . . .
H16 H 0.3807 0.9390 -0.0574 0.040 Uiso 1 1 calc R . .
C17 C 0.3053(2) 0.8760(2) -0.1449(3) 0.0384(10) Uani 1 1 d . . .
H17 H 0.3244 0.8432 -0.1589 0.046 Uiso 1 1 calc R . .
C18 C 0.1875(2) 0.8291(2) -0.2455(3) 0.0446(11) Uani 1 1 d . . .
C19 C 0.1598(3) 0.7910(2) -0.2036(4) 0.0666(15) Uani 1 1 d . . .
H19A H 0.1951 0.7690 -0.1490 0.100 Uiso 1 1 calc R . .
H19B H 0.1287 0.7574 -0.2454 0.100 Uiso 1 1 calc R . .
H19C H 0.1380 0.8227 -0.1899 0.100 Uiso 1 1 calc R . .
C20 C 0.1341(2) 0.8683(2) -0.3303(3) 0.0555(13) Uani 1 1 d . . .
H20A H 0.1122 0.8990 -0.3158 0.083 Uiso 1 1 calc R . .
H20B H 0.1025 0.8368 -0.3758 0.083 Uiso 1 1 calc R . .
H20C H 0.1540 0.8937 -0.3525 0.083 Uiso 1 1 calc R . .
C21 C 0.2192(3) 0.7777(2) -0.2712(3) 0.0609(14) Uani 1 1 d . . .
H21A H 0.2380 0.8015 -0.2961 0.091 Uiso 1 1 calc R . .
H21B H 0.1862 0.7464 -0.3152 0.091 Uiso 1 1 calc R . .
H21C H 0.2533 0.7530 -0.2183 0.091 Uiso 1 1 calc R . .
O1 O 0.14252(16) 0.92549(16) 0.0214(2) 0.0607(9) Uani 1 1 d DU . .
H1 H 0.1326 0.8855 0.0060 0.073 Uiso 1 1 calc R A 1
C22 C 0.0938(5) 0.9564(4) 0.0210(7) 0.125(3) Uani 0.848(4) 1 d PDU B 1
H22A H 0.0521 0.9483 -0.0377 0.150 Uiso 0.848(4) 1 calc PR B 1
H22B H 0.1017 1.0051 0.0262 0.150 Uiso 0.848(4) 1 calc PR B 1
C23 C 0.0855(5) 0.9368(4) 0.0894(7) 0.149(3) Uani 1 1 d DU . .
H23A H 0.0490 0.9613 0.0797 0.224 Uiso 1 1 calc R B 1
H23B H 0.1250 0.9476 0.1483 0.224 Uiso 1 1 calc R B 1
H23C H 0.0772 0.8888 0.0855 0.224 Uiso 1 1 calc R B 1
C22A C 0.1467(9) 0.940(3) 0.0979(14) 0.125(3) Uani 0.15 1 d PDU B -2
H22C H 0.1645 0.9861 0.1174 0.150 Uiso 0.152(4) 1 calc PR B -2
H22D H 0.1783 0.9094 0.1455 0.150 Uiso 0.152(4) 1 calc PR B -2
O2 O 0.1407(2) 0.7922(2) 0.0450(3) 0.0678(12) Uani 0.848(4) 1 d PDU . .
H2 H 0.1233 0.7735 0.0654 0.102 Uiso 0.848(4) 1 calc PR . .
C24 C 0.1269(4) 0.7549(3) -0.0296(5) 0.087(3) Uani 0.848(4) 1 d PDU . .
H24A H 0.1340 0.7068 -0.0145 0.104 Uiso 0.848(4) 1 calc PR . .
H24B H 0.1571 0.7688 -0.0426 0.104 Uiso 0.848(4) 1 calc PR . .
C25 C 0.0587(5) 0.7655(4) -0.1102(5) 0.121(4) Uani 0.848(4) 1 d PD . .
H25A H 0.0289 0.7569 -0.0954 0.181 Uiso 0.848(4) 1 calc PR . .
H25B H 0.0491 0.7348 -0.1571 0.181 Uiso 0.848(4) 1 calc PR . .
H25C H 0.0535 0.8116 -0.1307 0.181 Uiso 0.848(4) 1 calc PR . .
O7 O 0.0036(18) 0.9838(10) -0.2219(19) 0.103(11) Uani 0.152(4) 1 d PDU B -2
H7D H -0.0066 0.9966 -0.2709 0.154 Uiso 0.152(4) 1 calc PR B -2
C26 C 0.0055(11) 0.9133(10) -0.2186(13) 0.033(7) Uani 0.152(4) 1 d PDU B -2
H26A H 0.0379 0.8959 -0.2259 0.040 Uiso 0.152(4) 1 calc PR B -2
H26B H -0.0374 0.8943 -0.2658 0.040 Uiso 0.152(4) 1 calc PR B -2
C27 C 0.0241(10) 0.8961(11) -0.1286(12) 0.027(6) Uani 0.152(4) 1 d PDU B -2
H27A H 0.0263 0.8475 -0.1216 0.041 Uiso 0.152(4) 1 calc PR B -2
H27B H -0.0083 0.9140 -0.1226 0.041 Uiso 0.152(4) 1 calc PR B -2
H27C H 0.0664 0.9156 -0.0829 0.041 Uiso 0.152(4) 1 calc PR B -2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Zn Zn 0.2839 1.4301 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
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
_geom_angle_publ_flag
O1 Zn1 S1 108.91(10) . . ?
O1 Zn1 S3 112.98(10) . . ?
S1 Zn1 S3 108.95(4) . . ?
O1 Zn1 S2 105.39(10) . . ?
S1 Zn1 S2 110.69(4) . . ?
S3 Zn1 S2 109.88(4) . . ?
C1 S1 Zn1 93.31(12) . . ?
C8 S2 Zn1 95.31(12) . . ?
C15 S3 Zn1 96.88(12) . . ?
N1 B1 N3 112.6(3) . . ?
N1 B1 N5 113.1(3) . . ?
N3 B1 N5 112.6(3) . . ?
O6 Cl1 O5 108.9(2) . . ?
O6 Cl1 O3 110.6(2) . . ?
O5 Cl1 O3 111.3(2) . . ?
O6 Cl1 O4 109.4(3) . . ?
O5 Cl1 O4 107.5(2) . . ?
O3 Cl1 O4 109.0(2) . . ?
C1 N1 C2 107.7(3) . . ?
C1 N1 B1 134.1(3) . . ?
C2 N1 B1 118.1(3) . . ?
C1 N2 C3 108.4(3) . . ?
C1 N2 C4 127.0(3) . . ?
C3 N2 C4 124.6(3) . . ?
C8 N3 C9 107.9(3) . . ?
C8 N3 B1 133.6(3) . . ?
C9 N3 B1 118.5(3) . . ?
C8 N4 C10 108.1(3) . . ?
C8 N4 C11 127.5(3) . . ?
C10 N4 C11 124.4(3) . . ?
C15 N5 C16 108.2(3) . . ?
C15 N5 B1 133.1(3) . . ?
C16 N5 B1 118.6(3) . . ?
C15 N6 C17 108.3(3) . . ?
C15 N6 C18 127.5(3) . . ?
C17 N6 C18 124.2(3) . . ?
N1 C1 N2 107.8(3) . . ?
N1 C1 S1 125.5(3) . . ?
N2 C1 S1 126.7(3) . . ?
C3 C2 N1 108.6(3) . . ?
C2 C3 N2 107.6(3) . . ?
N2 C4 C6 109.2(3) . . ?
N2 C4 C5 109.7(3) . . ?
C6 C4 C5 111.9(4) . . ?
N2 C4 C7 108.4(3) . . ?
C6 C4 C7 108.7(3) . . ?
C5 C4 C7 109.0(3) . . ?
N3 C8 N4 108.2(3) . . ?
N3 C8 S2 125.4(3) . . ?
N4 C8 S2 126.4(3) . . ?
C10 C9 N3 108.4(3) . . ?
C9 C10 N4 107.4(3) . . ?
C14 C11 N4 109.9(3) . . ?
C14 C11 C12 112.3(3) . . ?
N4 C11 C12 108.6(3) . . ?
C14 C11 C13 109.2(3) . . ?
N4 C11 C13 108.0(3) . . ?
C12 C11 C13 108.7(3) . . ?
N5 C15 N6 107.3(3) . . ?
N5 C15 S3 126.1(3) . . ?
N6 C15 S3 126.6(3) . . ?
C17 C16 N5 108.8(4) . . ?
C16 C17 N6 107.5(3) . . ?
N6 C18 C19 110.0(3) . . ?
N6 C18 C20 108.5(3) . . ?
C19 C18 C20 112.1(4) . . ?
N6 C18 C21 108.7(4) . . ?
C19 C18 C21 109.0(4) . . ?
C20 C18 C21 108.6(3) . . ?
C22 O1 C22A 55.1(14) . . ?
C22 O1 Zn1 131.5(4) . . ?
C22A O1 Zn1 124.4(12) . . ?
O1 C22 C23 118.6(7) . . ?
C22 C23 C22A 51.8(13) . . ?
O1 C22A C23 117.1(11) . . ?
O2 C24 C25 111.6(5) . . ?
O7 C26 C27 104.9(16) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 2.009(3) . ?
Zn1 S1 2.3200(11) . ?
Zn1 S3 2.3264(11) . ?
Zn1 S2 2.3268(11) . ?
S1 C1 1.730(4) . ?
S2 C8 1.736(4) . ?
S3 C15 1.726(4) . ?
O3 Cl1 1.426(3) . ?
O4 Cl1 1.442(4) . ?
O5 Cl1 1.407(3) . ?
O6 Cl1 1.401(4) . ?
B1 N1 1.549(5) . ?
B1 N3 1.559(5) . ?
B1 N5 1.563(5) . ?
N1 C1 1.355(4) . ?
N1 C2 1.387(5) . ?
N2 C1 1.366(4) . ?
N2 C3 1.377(5) . ?
N2 C4 1.508(5) . ?
N3 C8 1.345(5) . ?
N3 C9 1.384(4) . ?
N4 C8 1.359(5) . ?
N4 C10 1.383(5) . ?
N4 C11 1.516(5) . ?
N5 C15 1.354(5) . ?
N5 C16 1.375(5) . ?
N6 C15 1.365(5) . ?
N6 C17 1.382(5) . ?
N6 C18 1.511(5) . ?
C2 C3 1.340(5) . ?
C4 C6 1.518(5) . ?
C4 C5 1.522(6) . ?
C4 C7 1.533(5) . ?
C9 C10 1.339(5) . ?
C11 C14 1.514(6) . ?
C11 C12 1.530(5) . ?
C11 C13 1.532(5) . ?
C16 C17 1.331(5) . ?
C18 C19 1.520(6) . ?
C18 C20 1.528(6) . ?
C18 C21 1.531(6) . ?
O1 C22 1.372(7) . ?
O1 C22A 1.386(12) . ?
C22 C23 1.454(9) . ?
C23 C22A 1.463(13) . ?
O2 C24 1.409(7) . ?
C24 C25 1.469(10) . ?
O7 C26 1.385(16) . ?
C26 C27 1.473(16) . ?
