#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:34:44 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178905 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/34/4113411.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_4113411
loop_
_publ_author_name
'Jennifer N. Smith'
'Zahida Shirin'
'Carl J. Carrano'
_publ_section_title
;
 Control of Thiolate Nucleophilicity and Specificity in Zinc
 Metalloproteins by Hydrogen Bonding: Lessons from Model Compound Studies
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              868
_journal_page_last               869
_journal_paper_doi               10.1021/ja029418i
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C22 H29 N5 O S2 Zn'
_chemical_formula_weight         508.99
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 92.29(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.356(2)
_cell_length_b                   13.930(3)
_cell_length_c                   16.680(3)
_cell_measurement_reflns_used    5314
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     2404.3(8)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Nonius Kappa'
_diffrn_measurement_method       CCD
_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  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0538
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10381
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.08
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  n/a
_diffrn_standards_number         n/a
_exptl_absorpt_coefficient_mu    1.219
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    n/a
_exptl_crystal_description       rod
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.000
_refine_ls_goodness_of_fit_obs   1.048
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         5465
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_restrained_S_obs      1.048
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_obs          0.0407
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0461P)²+2.5831P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1066
_refine_ls_wR_factor_obs         0.0943
_reflns_number_observed          3957
_reflns_number_total             5465
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ja029418i_s3.cif
_cod_data_source_block           zs37
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'n/a' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0461P)^2^+2.5831P] 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^)+(0.0461P)^2^+2.5831P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               4113411
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
Zn1 Zn 0.24157(3) 0.21182(2) 0.03803(2) 0.02408(11) Uani 1 d .
S1 S 0.32599(7) 0.35950(5) 0.02112(4) 0.0276(2) Uani 1 d .
S2 S 0.07045(7) 0.16181(5) 0.10557(5) 0.0326(2) Uani 1 d .
N1 N 0.4101(2) 0.1362(2) 0.05763(13) 0.0220(5) Uani 1 d .
N2 N 0.5023(2) 0.1515(2) 0.00258(13) 0.0206(5) Uani 1 d .
N3 N 0.2506(2) 0.1670(2) -0.08038(13) 0.0225(5) Uani 1 d .
N4 N 0.3666(2) 0.1855(2) -0.11395(12) 0.0201(5) Uani 1 d .
N5 N -0.1005(2) 0.1946(2) 0.23830(15) 0.0325(6) Uani 1 d .
C1 C 0.7367(3) 0.1129(2) -0.0191(2) 0.0333(7) Uani 1 d .
H1A H 0.7218(3) 0.1506(2) -0.0667(2) 0.080 Uiso 1 d R
H1B H 0.8030(3) 0.1425(2) 0.0144(2) 0.080 Uiso 1 d R
H1C H 0.7637(3) 0.0495(2) -0.0336(2) 0.080 Uiso 1 d R
C2 C 0.6156(3) 0.1073(2) 0.0256(2) 0.0246(6) Uani 1 d .
C3 C 0.5933(3) 0.0612(2) 0.0966(2) 0.0288(6) Uani 1 d .
H3A H 0.6537(3) 0.0228(2) 0.1277(2) 0.080 Uiso 1 d R
C4 C 0.4653(3) 0.0805(2) 0.1145(2) 0.0258(6) Uani 1 d .
C5 C 0.3896(3) 0.0475(2) 0.1840(2) 0.0366(7) Uani 1 d .
H5A H 0.3036(3) 0.0730(2) 0.1791(2) 0.080 Uiso 1 d R
H5B H 0.3858(3) -0.0214(2) 0.1848(2) 0.080 Uiso 1 d R
H5C H 0.4311(3) 0.0701(2) 0.2329(2) 0.080 Uiso 1 d R
C6 C 0.4651(3) 0.1899(2) -0.2501(2) 0.0298(6) Uani 1 d .
H6A H 0.5413(3) 0.2086(2) -0.2192(2) 0.080 Uiso 1 d R
H6B H 0.4820(3) 0.1317(2) -0.2786(2) 0.080 Uiso 1 d R
H6C H 0.4418(3) 0.2397(2) -0.2877(2) 0.080 Uiso 1 d R
C7 C 0.3565(3) 0.1743(2) -0.1955(2) 0.0244(6) Uani 1 d .
C8 C 0.2308(3) 0.1475(2) -0.2135(2) 0.0293(6) Uani 1 d .
H8A H 0.1936(3) 0.1340(2) -0.2659(2) 0.080 Uiso 1 d R
C9 C 0.1685(3) 0.1430(2) -0.1406(2) 0.0268(6) Uani 1 d .
C10 C 0.0327(3) 0.1150(2) -0.1240(2) 0.0384(7) Uani 1 d .
H10A H 0.0197(3) 0.1198(2) -0.0675(2) 0.080 Uiso 1 d R
H10B H -0.0268(3) 0.1569(2) -0.1526(2) 0.080 Uiso 1 d R
H10C H 0.0181(3) 0.0501(2) -0.1413(2) 0.080 Uiso 1 d R
C11 C 0.4768(2) 0.2186(2) -0.06360(15) 0.0200(5) Uani 1 d .
H11A H 0.5509(2) 0.2144(2) -0.09624(15) 0.080 Uiso 1 d R
C12 C 0.4682(3) 0.3258(2) -0.0369(2) 0.0219(6) Uani 1 d .
C13 C 0.5918(3) 0.3476(2) 0.0131(2) 0.0313(7) Uani 1 d .
H13A H 0.6652(3) 0.3302(2) -0.0172(2) 0.080 Uiso 1 d R
H13B H 0.5960(3) 0.4147(2) 0.0259(2) 0.080 Uiso 1 d R
H13C H 0.5921(3) 0.3107(2) 0.0617(2) 0.080 Uiso 1 d R
C14 C 0.4645(3) 0.3862(2) -0.1137(2) 0.0303(7) Uani 1 d .
H14A H 0.5376(3) 0.3709(2) -0.1448(2) 0.080 Uiso 1 d R
H14B H 0.3863(3) 0.3723(2) -0.1443(2) 0.080 Uiso 1 d R
H14C H 0.4666(3) 0.4532(2) -0.1001(2) 0.080 Uiso 1 d R
C15 C -0.0220(3) 0.2677(2) 0.1187(2) 0.0249(6) Uani 1 d .
C16 C -0.0222(3) 0.3447(2) 0.0654(2) 0.0312(7) Uani 1 d .
H16A H 0.0313(3) 0.3409(2) 0.0198(2) 0.080 Uiso 1 d R
C17 C -0.0969(3) 0.4257(2) 0.0770(2) 0.0319(7) Uani 1 d .
H17A H -0.0968(3) 0.4774(2) 0.0390(2) 0.080 Uiso 1 d R
C18 C -0.1722(3) 0.4315(2) 0.1431(2) 0.0322(7) Uani 1 d .
H18A H -0.2230(3) 0.4879(2) 0.1519(2) 0.080 Uiso 1 d R
C19 C -0.1752(3) 0.3563(2) 0.1969(2) 0.0310(7) Uani 1 d .
H19A H -0.2266(3) 0.3610(2) 0.2434(2) 0.080 Uiso 1 d R
O1 O -0.2574(2) 0.2320(2) 0.32464(13) 0.0401(5) Uani 1 d .
C20 C -0.1015(3) 0.2741(2) 0.1852(2) 0.0265(6) Uani 1 d .
C21 C -0.1763(3) 0.1766(2) 0.3014(2) 0.0327(7) Uani 1 d .
C22 C -0.1506(4) 0.0813(3) 0.3417(2) 0.0514(10) Uani 1 d .
H22A H -0.2078(4) 0.0739(3) 0.3852(2) 0.080 Uiso 1 d R
H22B H -0.1650(4) 0.0302(3) 0.3039(2) 0.080 Uiso 1 d R
H22C H -0.0627(4) 0.0794(3) 0.3622(2) 0.080 Uiso 1 d R
H100 H -0.0433(42) 0.1506(32) 0.2265(26) 0.080 Uiso 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'
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'
O O 0.0106 0.0060 '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
N1 Zn1 N3 85.81(9)
N1 Zn1 S2 116.31(7)
N3 Zn1 S2 116.73(7)
N1 Zn1 S1 99.00(7)
N3 Zn1 S1 97.04(7)
S2 Zn1 S1 131.45(3)
C12 S1 Zn1 98.88(9)
C15 S2 Zn1 104.13(9)
C4 N1 N2 106.1(2)
C4 N1 Zn1 138.4(2)
N2 N1 Zn1 115.1(2)
N1 N2 C2 110.8(2)
N1 N2 C11 119.8(2)
C2 N2 C11 128.9(2)
C9 N3 N4 106.4(2)
C9 N3 Zn1 137.8(2)
N4 N3 Zn1 113.9(2)
C7 N4 N3 110.5(2)
C7 N4 C11 129.3(2)
N3 N4 C11 120.0(2)
C21 N5 C20 129.6(3)
N2 C2 C3 106.3(2)
N2 C2 C1 124.6(2)
C3 C2 C1 129.1(3)
C2 C3 C4 106.7(2)
N1 C4 C3 110.0(2)
N1 C4 C5 120.4(3)
C3 C4 C5 129.6(3)
N4 C7 C8 106.3(2)
N4 C7 C6 124.0(2)
C8 C7 C6 129.6(3)
C7 C8 C9 106.8(2)
N3 C9 C8 109.9(2)
N3 C9 C10 120.2(3)
C8 C9 C10 129.9(3)
N2 C11 N4 110.2(2)
N2 C11 C12 114.0(2)
N4 C11 C12 114.3(2)
C13 C12 C14 109.8(2)
C13 C12 C11 106.7(2)
C14 C12 C11 106.7(2)
C13 C12 S1 109.3(2)
C14 C12 S1 107.7(2)
C11 C12 S1 116.5(2)
C16 C15 C20 117.9(3)
C16 C15 S2 123.1(2)
C20 C15 S2 119.0(2)
C17 C16 C15 121.6(3)
C18 C17 C16 119.8(3)
C17 C18 C19 120.2(3)
C18 C19 C20 120.4(3)
C19 C20 C15 120.1(3)
C19 C20 N5 123.0(2)
C15 C20 N5 116.9(2)
O1 C21 N5 123.9(3)
O1 C21 C22 121.9(3)
N5 C21 C22 114.3(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Zn1 N1 2.054(2)
Zn1 N3 2.077(2)
Zn1 S2 2.2482(9)
Zn1 S1 2.2573(9)
S1 C12 1.854(3)
S2 C15 1.777(3)
N1 C4 1.336(3)
N1 N2 1.367(3)
N2 C2 1.367(3)
N2 C11 1.462(3)
N3 C9 1.333(3)
N3 N4 1.370(3)
N4 C7 1.370(3)
N4 C11 1.464(3)
N5 C21 1.360(4)
N5 C20 1.418(4)
C1 C2 1.487(4)
C2 C3 1.374(4)
C3 C4 1.396(4)
C4 C5 1.498(4)
C6 C7 1.491(4)
C7 C8 1.375(4)
C8 C9 1.400(4)
C9 C10 1.496(4)
C11 C12 1.563(4)
C12 C13 1.530(4)
C12 C14 1.531(4)
C15 C16 1.394(4)
C15 C20 1.410(4)
C16 C17 1.386(4)
C17 C18 1.379(4)
C18 C19 1.380(4)
C19 C20 1.395(4)
O1 C21 1.215(4)
C21 C22 1.508(4)
