#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/12/7151237.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_7151237
loop_
_publ_author_name
'Pedras, M Soledade C'
'Hossain, Mohammad'
_publ_section_title
;
 Metabolism of crucifer phytoalexins in Sclerotinia sclerotiorum:
 detoxification of strongly antifungal compounds involves
 glucosylation.
;
_journal_issue                   13
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2581
_journal_page_last               2590
_journal_paper_doi               10.1039/b604400j
_journal_volume                  4
_journal_year                    2006
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H18 N2 O7 S'
_chemical_formula_sum            'C16 H18 N2 O7 S'
_chemical_formula_weight         382.38
_chemical_name_systematic
;
?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 109.8086(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.8821(3)
_cell_length_b                   4.5502(2)
_cell_length_c                   14.6589(4)
_cell_measurement_reflns_used    2768
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     871.16(5)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1998)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_av_sigmaI/netI    0.0490
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10196
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.75
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.925
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'Shelxtl 6.10 (Bruker-AXS, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.10(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3438
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0399P)²+0.6333P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1090
_reflns_number_gt                3057
_reflns_number_total             3438
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            b604400j.txt
_cod_data_source_block           59
_cod_original_sg_symbol_Hall     'p 2yb'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7151237
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
S1' S -0.09864(6) 0.8775(2) 0.84057(7) 0.0452(3) Uani 1 1 d . . .
N1 N 0.08716(18) 0.7683(7) 0.80049(19) 0.0346(7) Uani 1 1 d . . .
N2' N -0.1756(2) 1.1091(8) 0.7584(2) 0.0471(8) Uani 1 1 d . . .
O1 O 0.13648(16) 0.5681(5) 0.87114(16) 0.0363(5) Uani 1 1 d . . .
O1" O 0.31018(12) 0.8806(5) 0.60287(12) 0.0202(4) Uani 1 1 d . . .
O2" O 0.40196(13) 0.4788(4) 0.50852(12) 0.0182(4) Uani 1 1 d . . .
H2"O H 0.3838 0.5997 0.4625 0.027 Uiso 1 1 calc R . .
O3" O 0.62429(12) 0.4531(4) 0.60589(12) 0.0168(4) Uani 1 1 d . . .
H3"O H 0.6219 0.6119 0.5760 0.025 Uiso 1 1 calc R . .
O4" O 0.67263(13) 0.3829(5) 0.81700(13) 0.0232(4) Uani 1 1 d . . .
H4"O H 0.7170 0.3450 0.7915 0.035 Uiso 1 1 calc R . .
O6" O 0.49034(16) 0.7940(4) 0.95157(14) 0.0269(5) Uani 1 1 d . . .
H6"O H 0.4888 0.6340 0.9796 0.040 Uiso 1 1 calc R . .
O5" O 0.44027(12) 0.8155(4) 0.74506(12) 0.0152(4) Uani 1 1 d . . .
C1" C 0.38484(18) 0.6798(6) 0.65562(17) 0.0149(5) Uani 1 1 d . . .
H1" H 0.3518 0.5015 0.6641 0.018 Uiso 1 1 d R . .
C2" C 0.45494(18) 0.6298(6) 0.59653(17) 0.0149(5) Uani 1 1 d . . .
H2" H 0.4781 0.8182 0.5829 0.018 Uiso 1 1 d R . .
C3" C 0.55022(17) 0.4599(6) 0.65480(17) 0.0151(5) Uani 1 1 d . . .
H3" H 0.5280 0.2637 0.6613 0.018 Uiso 1 1 d R . .
C4" C 0.59976(18) 0.5795(6) 0.75720(17) 0.0149(5) Uani 1 1 d . . .
H4" H 0.6331 0.7614 0.7531 0.018 Uiso 1 1 d R . .
C5" C 0.51830(18) 0.6256(6) 0.80438(18) 0.0152(5) Uani 1 1 d . . .
H5" H 0.4905 0.4379 0.8123 0.018 Uiso 1 1 d R . .
C6" C 0.56279(19) 0.7741(6) 0.90212(17) 0.0183(5) Uani 1 1 d . . .
H6"A H 0.5837 0.9697 0.8928 0.022 Uiso 1 1 d R . .
H6"B H 0.6210 0.6654 0.9423 0.022 Uiso 1 1 d R . .
C1 C 0.2008(3) 0.7204(13) 0.9550(3) 0.0671(14) Uani 1 1 d . . .
H1A H 0.2368 0.5852 1.0052 0.081 Uiso 1 1 d R . .
H1B H 0.2492 0.8331 0.9358 0.081 Uiso 1 1 d R . .
H1C H 0.1602 0.8503 0.9787 0.081 Uiso 1 1 d R . .
C2 C -0.0061(2) 0.8891(8) 0.7878(2) 0.0302(7) Uani 1 1 d . . .
C3 C -0.0345(2) 1.0723(7) 0.7078(2) 0.0283(7) Uani 1 1 d . . .
C3A C 0.04876(19) 1.0655(7) 0.6688(2) 0.0238(6) Uani 1 1 d . . .
C3' C -0.1329(2) 1.1896(9) 0.6941(3) 0.0415(9) Uani 1 1 d . . .
H3' H -0.1653 1.3187 0.6407 0.050 Uiso 1 1 d R . .
C4 C 0.0674(2) 1.1988(7) 0.5911(2) 0.0271(6) Uani 1 1 d . . .
H4 H 0.0184 1.3317 0.5492 0.032 Uiso 1 1 d R . .
C5 C 0.1561(2) 1.1311(7) 0.5731(2) 0.0236(6) Uani 1 1 d . . .
H5 H 0.1693 1.2212 0.5193 0.028 Uiso 1 1 d R . .
C6 C 0.22727(18) 0.9339(6) 0.63262(18) 0.0186(5) Uani 1 1 d . . .
C7 C 0.21365(19) 0.8013(6) 0.71310(19) 0.0224(6) Uani 1 1 d . . .
H7 H 0.2653 0.6717 0.7532 0.027 Uiso 1 1 d R . .
C7A C 0.12239(19) 0.8712(8) 0.72770(19) 0.0241(6) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2' S1' C2 92.78(15) . . ?
C2 N1 O1 125.3(2) . . ?
C2 N1 C7A 108.9(3) . . ?
O1 N1 C7A 125.7(2) . . ?
C3' N2' S1' 110.8(2) . . ?
N1 O1 C1 109.4(3) . . ?
C6 O1" C1" 118.63(19) . . ?
C2" O2" H2"O 109.5 . . ?
C3" O3" H3"O 109.5 . . ?
C4" O4" H4"O 109.5 . . ?
C6" O6" H6"O 109.5 . . ?
C1" O5" C5" 111.20(19) . . ?
O1" C1" O5" 107.1(2) . . ?
O1" C1" C2" 106.21(19) . . ?
O5" C1" C2" 109.87(18) . . ?
O1" C1" H1" 109.0 . . ?
O5" C1" H1" 112.5 . . ?
C2" C1" H1" 111.8 . . ?
O2" C2" C3" 110.3(2) . . ?
O2" C2" C1" 110.69(18) . . ?
C3" C2" C1" 111.00(19) . . ?
O2" C2" H2" 110.4 . . ?
C3" C2" H2" 106.4 . . ?
C1" C2" H2" 108.0 . . ?
O3" C3" C2" 111.31(19) . . ?
O3" C3" C4" 109.76(18) . . ?
C2" C3" C4" 112.8(2) . . ?
O3" C3" H3" 109.7 . . ?
C2" C3" H3" 106.3 . . ?
C4" C3" H3" 106.7 . . ?
O4" C4" C3" 112.0(2) . . ?
O4" C4" C5" 106.90(19) . . ?
C3" C4" C5" 109.81(19) . . ?
O4" C4" H4" 109.0 . . ?
C3" C4" H4" 108.2 . . ?
C5" C4" H4" 110.9 . . ?
O5" C5" C6" 106.8(2) . . ?
O5" C5" C4" 109.43(19) . . ?
C6" C5" C4" 111.3(2) . . ?
O5" C5" H5" 111.1 . . ?
C6" C5" H5" 109.5 . . ?
C4" C5" H5" 108.8 . . ?
O6" C6" C5" 112.2(2) . . ?
O6" C6" H6"A 108.2 . . ?
C5" C6" H6"A 108.9 . . ?
O6" C6" H6"B 108.2 . . ?
C5" C6" H6"B 109.8 . . ?
H6"A C6" H6"B 109.5 . . ?
O1 C1 H1A 111.1 . . ?
O1 C1 H1B 107.6 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.7 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 110.1(2) . . ?
N1 C2 S1' 138.8(3) . . ?
C3 C2 S1' 111.1(2) . . ?
C2 C3 C3' 109.3(3) . . ?
C2 C3 C3A 106.6(2) . . ?
C3' C3 C3A 144.1(3) . . ?
C4 C3A C7A 118.7(2) . . ?
C4 C3A C3 135.0(3) . . ?
C7A C3A C3 106.3(3) . . ?
N2' C3' C3 116.0(3) . . ?
N2' C3' H3' 123.5 . . ?
C3 C3' H3' 120.6 . . ?
C5 C4 C3A 119.0(3) . . ?
C5 C4 H4 120.3 . . ?
C3A C4 H4 120.7 . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
O1" C6 C7 123.8(2) . . ?
O1" C6 C5 113.8(2) . . ?
C7 C6 C5 122.4(2) . . ?
C7A C7 C6 115.0(2) . . ?
C7A C7 H7 125.2 . . ?
C6 C7 H7 119.7 . . ?
C7 C7A N1 127.9(3) . . ?
C7 C7A C3A 124.0(3) . . ?
N1 C7A C3A 108.1(2) . . ?
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
S1' N2' 1.683(3) . ?
S1' C2 1.709(2) . ?
N1 C2 1.360(4) . ?
N1 O1 1.375(3) . ?
N1 C7A 1.397(4) . ?
N2' C3' 1.323(5) . ?
O1 C1 1.430(5) . ?
O1" C6 1.383(3) . ?
O1" C1" 1.401(3) . ?
O2" C2" 1.426(3) . ?
O2" H2"O 0.8400 . ?
O3" C3" 1.439(3) . ?
O3" H3"O 0.8400 . ?
O4" C4" 1.411(3) . ?
O4" H4"O 0.8400 . ?
O6" C6" 1.428(3) . ?
O6" H6"O 0.8400 . ?
O5" C1" 1.417(3) . ?
O5" C5" 1.428(3) . ?
C1" C2" 1.523(3) . ?
C1" H1" 0.9602 . ?
C2" C3" 1.520(3) . ?
C2" H2" 0.9602 . ?
C3" C4" 1.524(3) . ?
C3" H3" 0.9602 . ?
C4" C5" 1.527(3) . ?
C4" H4" 0.9601 . ?
C5" C6" 1.514(3) . ?
C5" H5" 0.9603 . ?
C6" H6"A 0.9602 . ?
C6" H6"B 0.9601 . ?
C1 H1A 0.9602 . ?
C1 H1B 0.9601 . ?
C1 H1C 0.9603 . ?
C2 C3 1.383(4) . ?
C3 C3' 1.416(4) . ?
C3 C3A 1.454(4) . ?
C3A C4 1.389(4) . ?
C3A C7A 1.405(4) . ?
C3' H3' 0.9601 . ?
C4 C5 1.379(4) . ?
C4 H4 0.9602 . ?
C5 C6 1.400(4) . ?
C5 H5 0.9600 . ?
C6 C7 1.394(4) . ?
C7 C7A 1.391(3) . ?
C7 H7 0.9602 . ?
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
O2" H2"O O3" 0.84 1.88 2.681(2) 159.5 2_656
O3" H3"O O2" 0.84 2.04 2.873(2) 172.5 2_656
O4" H4"O N2' 0.84 2.02 2.821(3) 157.9 1_645
O6" H6"O O6" 0.84 1.82 2.6469(18) 169.9 2_647
C2" H2" O2" 0.96 2.57 3.304(3) 133.2 2_656
C6" H6"B O4" 0.96 2.54 2.888(3) 101.7 .
C7 H7 O5" 0.96 2.56 3.020(3) 109.8 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 S1' N2' C3' 0.2(3) . . . . ?
C2 N1 O1 C1 -91.3(4) . . . . ?
C7A N1 O1 C1 91.6(4) . . . . ?
C6 O1" C1" O5" -71.9(3) . . . . ?
C6 O1" C1" C2" 170.7(2) . . . . ?
C5" O5" C1" O1" 179.71(17) . . . . ?
C5" O5" C1" C2" -65.3(2) . . . . ?
O1" C1" C2" O2" -67.6(3) . . . . ?
O5" C1" C2" O2" 176.8(2) . . . . ?
O1" C1" C2" C3" 169.5(2) . . . . ?
O5" C1" C2" C3" 54.0(3) . . . . ?
O2" C2" C3" O3" 66.3(2) . . . . ?
C1" C2" C3" O3" -170.6(2) . . . . ?
O2" C2" C3" C4" -169.73(19) . . . . ?
C1" C2" C3" C4" -46.7(3) . . . . ?
O3" C3" C4" O4" -68.9(3) . . . . ?
C2" C3" C4" O4" 166.28(19) . . . . ?
O3" C3" C4" C5" 172.5(2) . . . . ?
C2" C3" C4" C5" 47.7(3) . . . . ?
C1" O5" C5" C6" -172.64(18) . . . . ?
C1" O5" C5" C4" 66.8(2) . . . . ?
O4" C4" C5" O5" -178.0(2) . . . . ?
C3" C4" C5" O5" -56.3(3) . . . . ?
O4" C4" C5" C6" 64.3(3) . . . . ?
C3" C4" C5" C6" -174.0(2) . . . . ?
O5" C5" C6" O6" 66.2(3) . . . . ?
C4" C5" C6" O6" -174.4(2) . . . . ?
O1 N1 C2 C3 -177.6(3) . . . . ?
C7A N1 C2 C3 -0.1(4) . . . . ?
O1 N1 C2 S1' 1.4(6) . . . . ?
C7A N1 C2 S1' 178.8(3) . . . . ?
N2' S1' C2 N1 -178.5(4) . . . . ?
N2' S1' C2 C3 0.4(3) . . . . ?
N1 C2 C3 C3' 178.4(3) . . . . ?
S1' C2 C3 C3' -0.9(4) . . . . ?
N1 C2 C3 C3A -0.6(4) . . . . ?
S1' C2 C3 C3A -179.9(2) . . . . ?
C2 C3 C3A C4 -179.7(3) . . . . ?
C3' C3 C3A C4 1.9(7) . . . . ?
C2 C3 C3A C7A 1.1(3) . . . . ?
C3' C3 C3A C7A -177.3(5) . . . . ?
S1' N2' C3' C3 -0.8(4) . . . . ?
C2 C3 C3' N2' 1.1(5) . . . . ?
C3A C3 C3' N2' 179.4(4) . . . . ?
C7A C3A C4 C5 1.5(4) . . . . ?
C3 C3A C4 C5 -177.7(3) . . . . ?
C3A C4 C5 C6 -0.7(4) . . . . ?
C1" O1" C6 C7 0.6(4) . . . . ?
C1" O1" C6 C5 -178.2(2) . . . . ?
C4 C5 C6 O1" 177.6(3) . . . . ?
C4 C5 C6 C7 -1.2(4) . . . . ?
O1" C6 C7 C7A -176.5(3) . . . . ?
C5 C6 C7 C7A 2.3(4) . . . . ?
C6 C7 C7A N1 178.7(3) . . . . ?
C6 C7 C7A C3A -1.5(4) . . . . ?
C2 N1 C7A C7 -179.4(3) . . . . ?
O1 N1 C7A C7 -1.9(5) . . . . ?
C2 N1 C7A C3A 0.8(4) . . . . ?
O1 N1 C7A C3A 178.3(3) . . . . ?
C4 C3A C7A C7 -0.3(5) . . . . ?
C3 C3A C7A C7 179.0(3) . . . . ?
C4 C3A C7A N1 179.5(3) . . . . ?
C3 C3A C7A N1 -1.1(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9864195
