#------------------------------------------------------------------------------
#$Date: 2016-03-23 20:42:38 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179420 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/17/4331733.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_4331733
loop_
_publ_author_name
'Taka-aki Okamura'
'Yasuhito Ushijima'
'Yui Omi'
'Kiyotaka Onitsuka'
_publ_section_title
;
 Systematic Investigation of Relationship between Strength of NH...S
 Hydrogen Bond and Reactivity of Molybdoenzyme Models
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              381
_journal_page_last               394
_journal_paper_doi               10.1021/ic302149p
_journal_volume                  52
_journal_year                    2013
_chemical_formula_moiety         'C13 H18 N4 O S2'
_chemical_formula_sum            'C13 H18 N4 O S2'
_chemical_formula_weight         310.43
_chemical_name_systematic
; 
2,3-(i-PrS)2C6H3NHCON3
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      60
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2009-02-13
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.893(5)
_cell_length_b                   9.440(2)
_cell_length_c                   18.631(5)
_cell_measurement_reflns_used    16231
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_cell_volume                     3147.0(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID II'
_diffrn_measurement_method       ω
_diffrn_radiation_source
;
 MicroMax-007HF microfocus rotating anode x-ray gererator
;
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0723
_diffrn_reflns_av_sigmaI/netI    0.0476
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            23177
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.16
_exptl_absorpt_coefficient_mu    0.340
_exptl_absorpt_correction_T_max  0.9899
_exptl_absorpt_correction_T_min  0.9508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3600
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0497
_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)+(0.0774P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1266
_refine_ls_wR_factor_ref         0.1399
_reflns_number_gt                2566
_reflns_number_total             3600
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic302149p_si_002_1.cif
_cod_data_source_block           1
_cod_original_cell_volume        3147.1(15)
_cod_database_code               4331733
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, z'
'x, -y, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, -z'
'-x, y, -z-1/2'
'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
S1 S 0.37489(3) 0.30076(6) 0.82881(3) 0.04797(19) Uani 1 1 d .
S2 S 0.40973(3) 0.46522(6) 0.68922(3) 0.04159(18) Uani 1 1 d .
O1 O 0.41770(12) 0.12942(19) 0.47379(9) 0.0737(5) Uani 1 1 d .
N1 N 0.44786(11) 0.2851(2) 0.56309(10) 0.0497(5) Uani 1 1 d .
H1 H 0.4555(14) 0.367(3) 0.5708(14) 0.060 Uiso 1 1 d .
N2 N 0.45364(12) 0.3600(2) 0.44762(10) 0.0566(5) Uani 1 1 d .
N3 N 0.44441(11) 0.3229(2) 0.38329(10) 0.0542(5) Uani 1 1 d .
N4 N 0.43751(15) 0.2967(2) 0.32520(11) 0.0678(6) Uani 1 1 d .
C1 C 0.35283(14) 0.1683(3) 0.89705(12) 0.0536(6) Uani 1 1 d .
H5 H 0.3934 0.0955 0.8980 0.064 Uiso 1 1 calc R
C2 C 0.35261(16) 0.2478(3) 0.96808(13) 0.0642(7) Uani 1 1 d .
H6 H 0.3087 0.3097 0.9703 0.077 Uiso 1 1 calc R
H7 H 0.3981 0.3051 0.9719 0.077 Uiso 1 1 calc R
H8 H 0.3509 0.1797 1.0078 0.077 Uiso 1 1 calc R
C3 C 0.27863(16) 0.0949(3) 0.88469(15) 0.0763(8) Uani 1 1 d .
H9 H 0.2381 0.1643 0.8879 0.092 Uiso 1 1 calc R
H10 H 0.2714 0.0214 0.9212 0.092 Uiso 1 1 calc R
H11 H 0.2784 0.0513 0.8369 0.092 Uiso 1 1 calc R
C4 C 0.30982(12) 0.4967(2) 0.67367(12) 0.0464(5) Uani 1 1 d .
H12 H 0.2805 0.4411 0.7096 0.056 Uiso 1 1 calc R
C5 C 0.29705(15) 0.6537(3) 0.68738(15) 0.0656(7) Uani 1 1 d .
H13 H 0.2444 0.6767 0.6788 0.079 Uiso 1 1 calc R
H14 H 0.3286 0.7094 0.6550 0.079 Uiso 1 1 calc R
H15 H 0.3099 0.6760 0.7372 0.079 Uiso 1 1 calc R
C6 C 0.28491(14) 0.4540(3) 0.59887(13) 0.0619(7) Uani 1 1 d .
H16 H 0.3138 0.5071 0.5631 0.074 Uiso 1 1 calc R
H17 H 0.2316 0.4752 0.5931 0.074 Uiso 1 1 calc R
H18 H 0.2933 0.3523 0.5921 0.074 Uiso 1 1 calc R
C11 C 0.39785(11) 0.2011(2) 0.75151(11) 0.0419(5) Uani 1 1 d .
C12 C 0.41282(11) 0.2779(2) 0.68825(10) 0.0395(5) Uani 1 1 d .
C13 C 0.43201(12) 0.2046(2) 0.62519(12) 0.0445(5) Uani 1 1 d .
C14 C 0.43670(13) 0.0577(2) 0.62471(12) 0.0509(5) Uani 1 1 d .
H2 H 0.4500 0.0084 0.5821 0.061 Uiso 1 1 calc R
C15 C 0.42162(14) -0.0154(3) 0.68726(13) 0.0546(6) Uani 1 1 d .
H3 H 0.4246 -0.1158 0.6873 0.066 Uiso 1 1 calc R
C16 C 0.40222(13) 0.0542(2) 0.74995(13) 0.0518(6) Uani 1 1 d .
H4 H 0.3918 0.0012 0.7921 0.062 Uiso 1 1 calc R
C17 C 0.43743(13) 0.2444(2) 0.49444(12) 0.0490(5) 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C11 S1 C1 104.64(11)
C12 S2 C4 101.01(10)
C17 N1 C13 126.5(2)
C17 N1 H1 118.2(19)
C13 N1 H1 114.0(19)
N3 N2 C17 110.04(19)
N4 N3 N2 176.4(2)
C3 C1 C2 110.8(2)
C3 C1 S1 113.38(18)
C2 C1 S1 105.56(17)
C3 C1 H5 109.0
C2 C1 H5 109.0
S1 C1 H5 109.0
C1 C2 H6 109.5
C1 C2 H7 109.5
H6 C2 H7 109.5
C1 C2 H8 109.5
H6 C2 H8 109.5
H7 C2 H8 109.5
C1 C3 H9 109.5
C1 C3 H10 109.5
H9 C3 H10 109.5
C1 C3 H11 109.5
H9 C3 H11 109.5
H10 C3 H11 109.5
C6 C4 C5 111.6(2)
C6 C4 S2 112.83(16)
C5 C4 S2 106.13(16)
C6 C4 H12 108.7
C5 C4 H12 108.7
S2 C4 H12 108.7
C4 C5 H13 109.5
C4 C5 H14 109.5
H13 C5 H14 109.5
C4 C5 H15 109.5
H13 C5 H15 109.5
H14 C5 H15 109.5
C4 C6 H16 109.5
C4 C6 H17 109.5
H16 C6 H17 109.5
C4 C6 H18 109.5
H16 C6 H18 109.5
H17 C6 H18 109.5
C16 C11 C12 119.1(2)
C16 C11 S1 124.12(18)
C12 C11 S1 116.82(16)
C13 C12 C11 119.4(2)
C13 C12 S2 120.54(16)
C11 C12 S2 120.00(15)
C14 C13 C12 120.8(2)
C14 C13 N1 121.31(19)
C12 C13 N1 117.92(19)
C15 C14 C13 118.8(2)
C15 C14 H2 120.6
C13 C14 H2 120.6
C14 C15 C16 121.6(2)
C14 C15 H3 119.2
C16 C15 H3 119.2
C15 C16 C11 120.3(2)
C15 C16 H4 119.8
C11 C16 H4 119.8
O1 C17 N1 126.9(2)
O1 C17 N2 123.6(2)
N1 C17 N2 109.5(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C11 1.769(2)
S1 C1 1.826(2)
S2 C12 1.769(2)
S2 C4 1.835(2)
O1 C17 1.204(3)
N1 C17 1.349(3)
N1 C13 1.413(3)
N1 H1 0.80(3)
N2 N3 1.259(2)
N2 C17 1.427(3)
N3 N4 1.117(2)
C1 C3 1.515(4)
C1 C2 1.521(3)
C1 H5 1.0000
C2 H6 0.9800
C2 H7 0.9800
C2 H8 0.9800
C3 H9 0.9800
C3 H10 0.9800
C3 H11 0.9800
C4 C6 1.518(3)
C4 C5 1.521(3)
C4 H12 1.0000
C5 H13 0.9800
C5 H14 0.9800
C5 H15 0.9800
C6 H16 0.9800
C6 H17 0.9800
C6 H18 0.9800
C11 C16 1.389(3)
C11 C12 1.410(3)
C12 C13 1.406(3)
C13 C14 1.390(3)
C14 C15 1.380(3)
C14 H2 0.9500
C15 C16 1.384(3)
C15 H3 0.9500
C16 H4 0.9500
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
C11 S1 C1 C3 -72.7(2)
C11 S1 C1 C2 165.78(16)
C12 S2 C4 C6 -67.95(18)
C12 S2 C4 C5 169.48(16)
C1 S1 C11 C16 -4.3(2)
C1 S1 C11 C12 176.01(16)
C16 C11 C12 C13 -0.2(3)
S1 C11 C12 C13 179.48(16)
C16 C11 C12 S2 -178.58(17)
S1 C11 C12 S2 1.1(2)
C4 S2 C12 C13 96.02(18)
C4 S2 C12 C11 -85.61(17)
C11 C12 C13 C14 -0.3(3)
S2 C12 C13 C14 178.06(17)
C11 C12 C13 N1 -178.96(19)
S2 C12 C13 N1 -0.6(3)
C17 N1 C13 C14 30.5(3)
C17 N1 C13 C12 -150.9(2)
C12 C13 C14 C15 0.5(3)
N1 C13 C14 C15 179.1(2)
C13 C14 C15 C16 -0.1(4)
C14 C15 C16 C11 -0.4(4)
C12 C11 C16 C15 0.5(3)
S1 C11 C16 C15 -179.10(18)
C13 N1 C17 O1 -5.5(4)
C13 N1 C17 N2 174.6(2)
N3 N2 C17 O1 -0.2(3)
N3 N2 C17 N1 179.7(2)
