Unveiling the first indole-fused thiazepine: structure, synthesis and biosynthesis of cyclonasturlexin, a remarkable cruciferous phytoalexin
M. S. C. Pedras; Q. H. To; Chem.Commun. 52 (2016) 5880–; doi:

data_7119025
_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       '\f and \w 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/[\s^2^(Fo^2^)+(0.0717P)^2^+0.0610P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(I)'
_cod_data_source_file            c6cc02108e3.cif
_cod_data_source_block           1533_0m
_cod_database_code               7119025
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.801
_shelx_estimated_absorpt_t_max   0.947
_shelx_res_checksum              18031
_shelx_hkl_checksum              99681
_solvent_exptl_crystal_recrystallization_method dichloromethane