#------------------------------------------------------------------------------
#$Date: 2016-06-10 18:54:35 +0300 (Fri, 10 Jun 2016) $
#$Revision: 183313 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/90/7119025.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_7119025
loop_
_publ_author_name
'M. S. C. Pedras'
'Q. H. To'
_publ_section_title
;
 Unveiling the first indole-fused thiazepine: structure, synthesis and
 biosynthesis of cyclonasturlexin, a remarkable cruciferous phytoalexin
;
_journal_name_full               Chem.Commun.
_journal_page_first              5880
_journal_volume                  52
_journal_year                    2016
_chemical_compound_source        'watercress (Nasturtium officinale)'
_chemical_formula_moiety         'C11 H10 N2 S2'
_chemical_formula_sum            'C11 H10 N2 S2'
_chemical_formula_weight         234.33
_chemical_name_systematic        cyclonasturlexin
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-02-26 deposited with the CCDC.
2016-03-29 downloaded from the CCDC.
;
_cell_angle_alpha                91.652(2)
_cell_angle_beta                 103.923(2)
_cell_angle_gamma                90.151(2)
_cell_formula_units_Z            4
_cell_length_a                   9.2746(3)
_cell_length_b                   10.8353(4)
_cell_length_c                   11.1364(4)
_cell_measurement_reflns_used    8339
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.62
_cell_volume                     1085.75(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15698
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.534
_diffrn_reflns_theta_min         3.167
_exptl_absorpt_coefficient_mu    0.455
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0456
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0717P)²+0.0610P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1263
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3562
_reflns_number_total             4711
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6cc02108e3.cif
_cod_data_source_block           1533_0m
_cod_database_code               7119025
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.801
_shelx_estimated_absorpt_t_max   0.947
_solvent_exptl_crystal_recrystallization_method dichloromethane
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.80428(8) 0.88362(6) 0.70748(5) 0.04115(19) Uani 1 1 d . . . . .
S12 S 0.90958(7) 0.63453(6) 0.69909(6) 0.04102(19) Uani 1 1 d . . . . .
S24 S 0.70231(7) 0.35965(5) -0.08397(5) 0.03286(17) Uani 1 1 d . . . . .
S25 S 0.82522(6) 0.11705(5) -0.04036(5) 0.03087(17) Uani 1 1 d . . . . .
N1 N 0.6185(2) 1.02501(17) 0.27432(17) 0.0299(4) Uani 1 1 d . . . . .
H1 H 0.6024 1.0620 0.2031 0.036 Uiso 1 1 calc R U . . .
N9 N 0.6651(2) 0.70351(16) 0.53565(17) 0.0276(4) Uani 1 1 d . . . . .
N14 N 0.6295(2) 0.53923(17) 0.31568(17) 0.0320(4) Uani 1 1 d . . . . .
H14 H 0.6313 0.5832 0.3837 0.038 Uiso 1 1 calc R U . . .
N23 N 0.61430(19) 0.19171(15) 0.06931(16) 0.0245(4) Uani 1 1 d . . . . .
C2 C 0.5421(2) 0.9237(2) 0.2982(2) 0.0320(5) Uani 1 1 d . . . . .
H2 H 0.4639 0.8825 0.2399 0.038 Uiso 1 1 calc R U . . .
C3 C 0.5943(2) 0.89102(19) 0.4173(2) 0.0257(5) Uani 1 1 d . . . . .
C4 C 0.8085(3) 0.9885(2) 0.5882(2) 0.0297(5) Uani 1 1 d . . . . .
C5 C 0.9085(3) 1.0849(2) 0.6118(2) 0.0402(6) Uani 1 1 d . . . . .
H5 H 0.9743 1.0950 0.6913 0.048 Uiso 1 1 calc R U . . .
C6 C 0.9145(3) 1.1691(2) 0.5189(2) 0.0420(6) Uani 1 1 d . . . . .
H6 H 0.9839 1.2357 0.5377 0.050 Uiso 1 1 calc R U . . .
C7 C 0.8235(2) 1.1580(2) 0.4027(2) 0.0328(5) Uani 1 1 d . . . . .
H7 H 0.8284 1.2153 0.3408 0.039 Uiso 1 1 calc R U . . .
C8 C 0.5451(2) 0.7909(2) 0.4879(2) 0.0311(5) Uani 1 1 d . . . . .
H8A H 0.5104 0.8282 0.5580 0.037 Uiso 1 1 calc R U . . .
H8B H 0.4603 0.7456 0.4333 0.037 Uiso 1 1 calc R U . . .
C10 C 0.7717(3) 0.7363(2) 0.6258(2) 0.0288(5) Uani 1 1 d . . . . .
C13 C 0.8377(3) 0.4880(2) 0.6308(3) 0.0496(7) Uani 1 1 d . . . . .
H13A H 0.7329 0.4803 0.6322 0.074 Uiso 1 1 calc R U . . .
H13B H 0.8941 0.4214 0.6779 0.074 Uiso 1 1 calc R U . . .
H13C H 0.8471 0.4822 0.5450 0.074 Uiso 1 1 calc R U . . .
C15 C 0.5486(3) 0.4329(2) 0.2789(2) 0.0299(5) Uani 1 1 d . . . . .
H15 H 0.4863 0.3950 0.3238 0.036 Uiso 1 1 calc R U . . .
C16 C 0.5703(2) 0.38918(18) 0.1686(2) 0.0244(5) Uani 1 1 d . . . . .
C17 C 0.7417(2) 0.47452(18) 0.0369(2) 0.0245(5) Uani 1 1 d . . . . .
C18 C 0.8384(2) 0.5701(2) 0.0317(2) 0.0318(5) Uani 1 1 d . . . . .
H18 H 0.8864 0.5721 -0.0346 0.038 Uiso 1 1 calc R U . . .
C19 C 0.8662(2) 0.6642(2) 0.1235(2) 0.0343(6) Uani 1 1 d . . . . .
H19 H 0.9317 0.7299 0.1171 0.041 Uiso 1 1 calc R U . . .
C20 C 0.8017(2) 0.6643(2) 0.2225(2) 0.0328(5) Uani 1 1 d . . . . .
H20 H 0.8208 0.7289 0.2840 0.039 Uiso 1 1 calc R U . . .
C21 C 0.5021(2) 0.28039(18) 0.0910(2) 0.0268(5) Uani 1 1 d . . . . .
H21A H 0.4334 0.2382 0.1325 0.032 Uiso 1 1 calc R U . . .
H21B H 0.4432 0.3089 0.0104 0.032 Uiso 1 1 calc R U . . .
C24 C 0.6980(2) 0.22005(18) -0.00050(19) 0.0244(5) Uani 1 1 d . . . . .
C26 C 0.7789(3) -0.0236(2) 0.0232(2) 0.0384(6) Uani 1 1 d . . . . .
H26A H 0.8117 -0.0179 0.1137 0.058 Uiso 1 1 calc R U . . .
H26B H 0.8286 -0.0928 -0.0080 0.058 Uiso 1 1 calc R U . . .
H26C H 0.6711 -0.0369 -0.0013 0.058 Uiso 1 1 calc R U . . .
C3A C 0.7118(2) 0.97555(18) 0.47056(19) 0.0236(5) Uani 1 1 d . . . . .
C7A C 0.7233(2) 1.05920(19) 0.3787(2) 0.0265(5) Uani 1 1 d . . . . .
C16A C 0.6732(2) 0.47223(18) 0.13573(19) 0.0238(5) Uani 1 1 d . . . . .
C20A C 0.7075(2) 0.56612(19) 0.2288(2) 0.0264(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'
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
C4 S11 C10 103.26(10) . .
C10 S12 C13 102.10(12) . .
C17 S24 C24 102.39(9) . .
C24 S25 C26 101.76(11) . .
C7A N1 C2 109.10(18) . .
C7A N1 H1 125.4 . .
C2 N1 H1 125.4 . .
C10 N9 C8 119.71(19) . .
C15 N14 C20A 108.89(19) . .
C15 N14 H14 125.6 . .
C20A N14 H14 125.6 . .
C24 N23 C21 119.58(17) . .
C3 C2 N1 110.09(19) . .
C3 C2 H2 125.0 . .
N1 C2 H2 125.0 . .
C2 C3 C3A 106.40(19) . .
C2 C3 C8 130.4(2) . .
C3A C3 C8 123.2(2) . .
C5 C4 C3A 118.9(2) . .
C5 C4 S11 119.36(18) . .
C3A C4 S11 121.73(17) . .
C4 C5 C6 120.5(2) . .
C4 C5 H5 119.7 . .
C6 C5 H5 119.7 . .
C7 C6 C5 122.0(2) . .
C7 C6 H6 119.0 . .
C5 C6 H6 119.0 . .
C6 C7 C7A 117.3(2) . .
C6 C7 H7 121.4 . .
C7A C7 H7 121.4 . .
N9 C8 C3 112.07(17) . .
N9 C8 H8A 109.2 . .
C3 C8 H8A 109.2 . .
N9 C8 H8B 109.2 . .
C3 C8 H8B 109.2 . .
H8A C8 H8B 107.9 . .
N9 C10 S12 123.06(17) . .
N9 C10 S11 128.65(17) . .
S12 C10 S11 108.16(12) . .
S12 C13 H13A 109.5 . .
S12 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
S12 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C16 C15 N14 110.34(19) . .
C16 C15 H15 124.8 . .
N14 C15 H15 124.8 . .
C15 C16 C16A 106.18(19) . .
C15 C16 C21 129.6(2) . .
C16A C16 C21 124.19(19) . .
C18 C17 C16A 119.1(2) . .
C18 C17 S24 119.60(16) . .
C16A C17 S24 121.30(16) . .
C17 C18 C19 120.4(2) . .
C17 C18 H18 119.8 . .
C19 C18 H18 119.8 . .
C20 C19 C18 122.0(2) . .
C20 C19 H19 119.0 . .
C18 C19 H19 119.0 . .
C19 C20 C20A 117.2(2) . .
C19 C20 H20 121.4 . .
C20A C20 H20 121.4 . .
N23 C21 C16 112.28(17) . .
N23 C21 H21A 109.1 . .
C16 C21 H21A 109.1 . .
N23 C21 H21B 109.1 . .
C16 C21 H21B 109.1 . .
H21A C21 H21B 107.9 . .
N23 C24 S25 122.84(16) . .
N23 C24 S24 129.01(16) . .
S25 C24 S24 108.00(11) . .
S25 C26 H26A 109.5 . .
S25 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
S25 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
C4 C3A C7A 119.2(2) . .
C4 C3A C3 133.4(2) . .
C7A C3A C3 107.40(19) . .
N1 C7A C7 131.0(2) . .
N1 C7A C3A 107.00(18) . .
C7 C7A C3A 122.0(2) . .
C17 C16A C20A 119.1(2) . .
C17 C16A C16 133.3(2) . .
C20A C16A C16 107.66(19) . .
N14 C20A C20 130.9(2) . .
N14 C20A C16A 106.92(19) . .
C20 C20A C16A 122.1(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S11 C4 1.780(2) .
S11 C10 1.802(2) .
S12 C10 1.753(2) .
S12 C13 1.796(3) .
S24 C17 1.777(2) .
S24 C24 1.803(2) .
S25 C24 1.751(2) .
S25 C26 1.793(2) .
N1 C7A 1.365(3) .
N1 C2 1.372(3) .
N1 H1 0.8800 .
N9 C10 1.270(3) .
N9 C8 1.473(3) .
N14 C15 1.371(3) .
N14 C20A 1.377(3) .
N14 H14 0.8800 .
N23 C24 1.267(3) .
N23 C21 1.476(3) .
C2 C3 1.355(3) .
C2 H2 0.9500 .
C3 C3A 1.425(3) .
C3 C8 1.491(3) .
C4 C5 1.372(3) .
C4 C3A 1.401(3) .
C5 C6 1.409(3) .
C5 H5 0.9500 .
C6 C7 1.367(3) .
C6 H6 0.9500 .
C7 C7A 1.393(3) .
C7 H7 0.9500 .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C15 C16 1.364(3) .
C15 H15 0.9500 .
C16 C16A 1.427(3) .
C16 C21 1.487(3) .
C17 C18 1.379(3) .
C17 C16A 1.398(3) .
C18 C19 1.401(3) .
C18 H18 0.9500 .
C19 C20 1.376(3) .
C19 H19 0.9500 .
C20 C20A 1.389(3) .
C20 H20 0.9500 .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
C26 H26C 0.9800 .
C3A C7A 1.409(3) .
C16A C20A 1.411(3) .
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
N1 H1 N23 0.88 2.10 2.945(2) 161.1 1_565
N14 H14 N9 0.88 2.07 2.939(3) 170.0 .
C15 H15 N9 0.95 2.59 3.537(3) 174.8 2_666
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
C7A N1 C2 C3 0.4(3) . . . .
N1 C2 C3 C3A -0.9(2) . . . .
N1 C2 C3 C8 177.8(2) . . . .
C10 S11 C4 C5 -141.5(2) . . . .
C10 S11 C4 C3A 38.7(2) . . . .
C3A C4 C5 C6 -0.4(4) . . . .
S11 C4 C5 C6 179.86(19) . . . .
C4 C5 C6 C7 -0.7(4) . . . .
C5 C6 C7 C7A 0.0(4) . . . .
C10 N9 C8 C3 72.8(2) . . . .
C2 C3 C8 N9 120.8(3) . . . .
C3A C3 C8 N9 -60.7(3) . . . .
C8 N9 C10 S12 173.43(15) . . . .
C8 N9 C10 S11 -1.9(3) . . . .
C13 S12 C10 N9 -8.7(2) . . . .
C13 S12 C10 S11 167.40(12) . . . .
C4 S11 C10 N9 -57.2(2) . . . .
C4 S11 C10 S12 126.96(12) . . . .
C20A N14 C15 C16 -0.6(3) . . . .
N14 C15 C16 C16A 1.1(2) . . . .
N14 C15 C16 C21 -177.33(19) . . . .
C24 S24 C17 C18 140.07(17) . . . .
C24 S24 C17 C16A -41.91(19) . . . .
C16A C17 C18 C19 -0.7(3) . . . .
S24 C17 C18 C19 177.41(17) . . . .
C17 C18 C19 C20 1.2(3) . . . .
C18 C19 C20 C20A 0.4(3) . . . .
C24 N23 C21 C16 -70.4(3) . . . .
C15 C16 C21 N23 -121.9(2) . . . .
C16A C16 C21 N23 59.9(3) . . . .
C21 N23 C24 S25 -175.40(15) . . . .
C21 N23 C24 S24 -0.4(3) . . . .
C26 S25 C24 N23 7.4(2) . . . .
C26 S25 C24 S24 -168.50(11) . . . .
C17 S24 C24 N23 60.0(2) . . . .
C17 S24 C24 S25 -124.47(11) . . . .
C5 C4 C3A C7A 2.1(3) . . . .
S11 C4 C3A C7A -178.09(15) . . . .
C5 C4 C3A C3 -177.6(2) . . . .
S11 C4 C3A C3 2.1(3) . . . .
C2 C3 C3A C4 -179.2(2) . . . .
C8 C3 C3A C4 2.1(4) . . . .
C2 C3 C3A C7A 1.0(2) . . . .
C8 C3 C3A C7A -177.76(19) . . . .
C2 N1 C7A C7 -177.1(2) . . . .
C2 N1 C7A C3A 0.3(2) . . . .
C6 C7 C7A N1 178.9(2) . . . .
C6 C7 C7A C3A 1.9(3) . . . .
C4 C3A C7A N1 179.37(18) . . . .
C3 C3A C7A N1 -0.8(2) . . . .
C4 C3A C7A C7 -3.0(3) . . . .
C3 C3A C7A C7 176.87(19) . . . .
C18 C17 C16A C20A -1.5(3) . . . .
S24 C17 C16A C20A -179.53(15) . . . .
C18 C17 C16A C16 -180.0(2) . . . .
S24 C17 C16A C16 2.0(3) . . . .
C15 C16 C16A C17 177.4(2) . . . .
C21 C16 C16A C17 -4.1(4) . . . .
C15 C16 C16A C20A -1.2(2) . . . .
C21 C16 C16A C20A 177.33(19) . . . .
C15 N14 C20A C20 178.4(2) . . . .
C15 N14 C20A C16A -0.2(2) . . . .
C19 C20 C20A N14 178.9(2) . . . .
C19 C20 C20A C16A -2.7(3) . . . .
C17 C16A C20A N14 -177.96(18) . . . .
C16 C16A C20A N14 0.9(2) . . . .
C17 C16A C20A C20 3.3(3) . . . .
C16 C16A C20A C20 -177.92(18) . . . .
