#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/10/7111024.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7111024
loop_
_publ_author_name
'Hammes, Brian S.'
'Carrano, Carl J.'
_publ_section_title
;
 Methylation of (2-methylethanethiol-bis-3,5-dimethylpyrazolyl)methane
 zinc complexes and coordination of the resulting thioether: relevance to
 zinc-containing alkyl transfer enzymes
;
_journal_issue                   17
_journal_name_full               'Chemical Communications'
_journal_page_first              1635
_journal_paper_doi               10.1039/b004338i
_journal_year                    2000
_chemical_formula_sum            'C17 H24 B0.5 F2 N4 O3.5 S Zn'
_chemical_formula_weight         481.24
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           154
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 32 2"'
_symmetry_space_group_name_H-M   'P 32 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   17.674(5)
_cell_length_b                   17.674(5)
_cell_length_c                   15.531(3)
_cell_measurement_temperature    293(2)
_cell_volume                     4201.5(19)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_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  0.0501
_diffrn_reflns_av_sigmaI/netI    0.0616
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4025
_diffrn_reflns_theta_max         22.52
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    0.986
_exptl_crystal_density_diffrn    1.141
_exptl_crystal_F_000             1491
_refine_diff_density_max         0.962
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.135
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.990
_refine_ls_goodness_of_fit_obs   0.965
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3515
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_restrained_S_obs      0.966
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_obs          0.0728
_refine_ls_shift/esd_max         -0.101
_refine_ls_shift/esd_mean        0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1935P)²+5.1911P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2508
_refine_ls_wR_factor_obs         0.2119
_reflns_number_observed          2859
_reflns_number_total             3522
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b004338isup1.cif
_cod_data_source_block           bsh43'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Trigonal' changed to 'trigonal'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1935P)^2^+5.1911P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1935P)^2^+5.1911P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P3(2)21
_cod_original_formula_sum        'C17 H24 B0.50 F2 N4 O3.50 S Zn'
_cod_database_code               7111024
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'y, x, -z'
'x-y, -y, -z+1/3'
'-x, -x+y, -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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Zn1 Zn 0.41298(8) 0.52308(8) 0.96827(7) 0.0359(4) Uani 1 d . .
S1 S 0.2659(2) 0.4532(2) 1.0546(2) 0.0378(7) Uani 1 d . .
N1 N 0.3256(6) 0.4659(6) 0.8588(5) 0.035(2) Uani 1 d . .
N2 N 0.2603(5) 0.4807(6) 0.8474(5) 0.036(2) Uani 1 d . .
N3 N 0.3981(5) 0.6326(6) 0.9464(5) 0.030(2) Uani 1 d . .
N4 N 0.3199(5) 0.6207(6) 0.9122(5) 0.032(2) Uani 1 d . .
O1 O 0.4158(5) 0.4158(5) 1.0000 0.024(2) Uani 1 d S .
O2 O 0.4907(5) 0.5855(5) 1.0809(5) 0.039(2) Uani 1 d . .
O3 O 0.5252(5) 0.5746(5) 0.8927(5) 0.042(2) Uani 1 d . .
C1 C 0.3932(9) 0.3891(9) 0.7829(8) 0.057(3) Uani 1 d . .
H1B H 0.4337(9) 0.4112(9) 0.8300(8) 0.085 Uiso 1 calc R .
H1C H 0.4242(9) 0.4111(9) 0.7296(8) 0.085 Uiso 1 calc R .
H1D H 0.3640(9) 0.3264(9) 0.7827(8) 0.085 Uiso 1 calc R .
C2 C 0.3250(7) 0.4188(7) 0.7930(6) 0.036(3) Uani 1 d . .
C3 C 0.2548(8) 0.4021(8) 0.7403(7) 0.047(3) Uani 1 d . .
H3B H 0.2388(8) 0.3690(8) 0.6901(7) 0.056 Uiso 1 calc R .
C4 C 0.2149(8) 0.4412(8) 0.7736(7) 0.048(3) Uani 1 d . .
C5 C 0.1386(9) 0.4481(11) 0.7390(8) 0.065(4) Uani 1 d . .
H5A H 0.1246(9) 0.4811(11) 0.7785(8) 0.098 Uiso 1 calc R .
H5B H 0.0889(9) 0.3906(11) 0.7325(8) 0.098 Uiso 1 calc R .
H5C H 0.1538(9) 0.4770(11) 0.6842(8) 0.098 Uiso 1 calc R .
C6 C 0.5463(7) 0.7607(7) 0.9680(7) 0.042(3) Uani 1 d . .
H6A H 0.5584(7) 0.7168(7) 0.9892(7) 0.063 Uiso 1 calc R .
H6B H 0.5590(7) 0.8035(7) 1.0121(7) 0.063 Uiso 1 calc R .
H6C H 0.5820(7) 0.7885(7) 0.9185(7) 0.063 Uiso 1 calc R .
C7 C 0.4526(7) 0.7194(8) 0.9436(6) 0.037(3) Uani 1 d . .
C8 C 0.4112(8) 0.7627(7) 0.9102(6) 0.038(3) Uani 1 d . .
H8A H 0.4356(8) 0.8226(7) 0.9030(6) 0.046 Uiso 1 calc R .
C9 C 0.3267(8) 0.6987(9) 0.8900(7) 0.048(3) Uani 1 d . .
C10 C 0.2546(9) 0.7072(9) 0.8492(9) 0.058(4) Uani 1 d . .
H10A H 0.2036(9) 0.6504(9) 0.8438(9) 0.087 Uiso 1 calc R .
H10B H 0.2727(9) 0.7330(9) 0.7931(9) 0.087 Uiso 1 calc R .
H10C H 0.2412(9) 0.7436(9) 0.8844(9) 0.087 Uiso 1 calc R .
C11 C 0.2429(7) 0.5347(7) 0.9067(6) 0.033(2) Uani 1 d . .
H11A H 0.1987(7) 0.5438(7) 0.8779(6) 0.039 Uiso 1 calc R .
C12 C 0.2020(8) 0.4931(8) 0.9960(6) 0.038(3) Uani 1 d . .
C13 C 0.1987(8) 0.5596(9) 1.0527(7) 0.049(3) Uani 1 d . .
H13A H 0.1736(8) 0.5335(9) 1.1072(7) 0.074 Uiso 1 calc R .
H13B H 0.1635(8) 0.5803(9) 1.0259(7) 0.074 Uiso 1 calc R .
H13C H 0.2568(8) 0.6076(9) 1.0614(7) 0.074 Uiso 1 calc R .
C14 C 0.1049(7) 0.4171(9) 0.9767(8) 0.052(3) Uani 1 d . .
H14A H 0.1065(7) 0.3740(9) 0.9403(8) 0.077 Uiso 1 calc R .
H14B H 0.0733(7) 0.4410(9) 0.9484(8) 0.077 Uiso 1 calc R .
H14C H 0.0764(7) 0.3903(9) 1.0299(8) 0.077 Uiso 1 calc R .
C15 C 0.2215(10) 0.3426(8) 1.0222(10) 0.065(4) Uani 1 d . .
H15A H 0.2522(10) 0.3177(8) 1.0507(10) 0.097 Uiso 1 calc R .
H15B H 0.2276(10) 0.3402(8) 0.9610(10) 0.097 Uiso 1 calc R .
H15C H 0.1608(10) 0.3103(8) 1.0373(10) 0.097 Uiso 1 calc R .
C16 C 0.5618(10) 0.5910(10) 1.1111(8) 0.056(3) Uani 1 d . 1
C17 C 0.6200(16) 0.6639(16) 1.1612(16) 0.008(10) Uiso 0.32(4) d P 1
C17' C 0.6377(18) 0.6593(17) 1.0737(16) 0.011(10) Uiso 0.29(3) d P 2
C17" C 0.5784(15) 0.6301(15) 1.2056(15) 0.024(9) Uiso 0.42(4) d P 3
B1 B 0.4347(12) 0.4347(12) 0.5000 0.050(5) Uani 1 d S .
F1 F 0.4486(10) 0.5031(10) 0.5463(9) 0.152(6) Uani 1 d . .
F2 F 0.4283(14) 0.3750(11) 0.5534(10) 0.191(8) Uani 1 d . .
O4 O 0.1479(37) 0.2315(30) 0.5404(32) 0.270(29) Uani 0.50 d P .
O5 O 0.0000 0.1930(18) 0.8333 0.345(31) Uani 1 d S .
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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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'
Zn Zn 0.2839 1.4301 '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 Zn1 O3 94.8(3) . .
O1 Zn1 N3 172.9(3) . .
O3 Zn1 N3 92.1(3) . .
O1 Zn1 O2 88.5(2) . .
O3 Zn1 O2 90.6(3) . .
N3 Zn1 O2 90.1(3) . .
O1 Zn1 N1 95.8(3) . .
O3 Zn1 N1 93.5(3) . .
N3 Zn1 N1 85.1(3) . .
O2 Zn1 N1 173.8(3) . .
O1 Zn1 S1 85.1(2) . .
O3 Zn1 S1 176.3(2) . .
N3 Zn1 S1 88.0(2) . .
O2 Zn1 S1 93.1(2) . .
N1 Zn1 S1 82.8(2) . .
C15 S1 C12 105.2(6) . .
C15 S1 Zn1 99.3(5) . .
C12 S1 Zn1 102.7(4) . .
C2 N1 N2 106.8(8) . .
C2 N1 Zn1 132.9(8) . .
N2 N1 Zn1 120.1(6) . .
N1 N2 C4 111.0(9) . .
N1 N2 C11 122.3(8) . .
C4 N2 C11 126.6(9) . .
C7 N3 N4 104.5(8) . .
C7 N3 Zn1 135.0(7) . .
N4 N3 Zn1 119.5(6) . .
C9 N4 N3 111.4(9) . .
C9 N4 C11 127.2(9) . .
N3 N4 C11 121.3(8) . .
Zn1 O1 Zn1 124.5(4) 4_557 .
C16 O2 Zn1 132.6(7) . .
C16 O3 Zn1 133.9(8) 4_557 .
N1 C2 C3 108.5(10) . .
N1 C2 C1 122.2(10) . .
C3 C2 C1 129.3(10) . .
C4 C3 C2 108.2(10) . .
C3 C4 N2 105.4(11) . .
C3 C4 C5 129.6(11) . .
N2 C4 C5 125.0(12) . .
N3 C7 C8 111.4(9) . .
N3 C7 C6 122.6(10) . .
C8 C7 C6 125.8(11) . .
C9 C8 C7 106.5(10) . .
N4 C9 C8 106.3(10) . .
N4 C9 C10 124.0(12) . .
C8 C9 C10 129.7(12) . .
N4 C11 N2 109.1(8) . .
N4 C11 C12 114.2(8) . .
N2 C11 C12 116.7(8) . .
C13 C12 C11 110.1(9) . .
C13 C12 C14 109.0(10) . .
C11 C12 C14 106.2(9) . .
C13 C12 S1 106.5(7) . .
C11 C12 S1 112.9(7) . .
C14 C12 S1 112.2(8) . .
O3 C16 O2 120.9(13) 4_557 .
O3 C16 C17 118.1(14) 4_557 .
O2 C16 C17 120.2(14) . .
F2 B1 F2 126.7(27) 4_556 .
F2 B1 F1 101.5(10) 4_556 .
F2 B1 F1 107.2(9) . .
F2 B1 F1 107.2(9) 4_556 4_556
F2 B1 F1 101.5(10) . 4_556
F1 B1 F1 113.1(22) . 4_556
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O1 1.984(4) .
Zn1 O3 2.082(7) .
Zn1 N3 2.107(9) .
Zn1 O2 2.156(7) .
Zn1 N1 2.176(9) .
Zn1 S1 2.621(3) .
S1 C15 1.776(13) .
S1 C12 1.844(11) .
N1 C2 1.315(13) .
N1 N2 1.318(12) .
N2 C4 1.372(14) .
N2 C11 1.465(13) .
N3 C7 1.34(2) .
N3 N4 1.395(12) .
N4 C9 1.37(2) .
N4 C11 1.450(14) .
O1 Zn1 1.984(4) 4_557
O2 C16 1.30(2) .
O3 C16 1.29(2) 4_557
C1 C2 1.54(2) .
C2 C3 1.39(2) .
C3 C4 1.32(2) .
C4 C5 1.51(2) .
C6 C7 1.49(2) .
C7 C8 1.40(2) .
C8 C9 1.39(2) .
C9 C10 1.50(2) .
C11 C12 1.568(15) .
C12 C13 1.49(2) .
C12 C14 1.59(2) .
C16 O3 1.29(2) 4_557
C16 C17 1.41(3) .
B1 F2 1.30(2) 4_556
B1 F2 1.30(2) .
B1 F1 1.32(2) .
B1 F1 1.32(2) 4_556
