Divergent reactivity of an indole glucosinolate yields Lossen or Neber rearrangement products: the phytoalexin rapalexin A or a unique β-d-glucopyranose fused heterocycle.
Pedras, M. S. C.; To, Q. H.; Schatte, G.; Chemical communications (Cambridge, England) 52 (2016) 2505–2508; doi:10.1039/c5cc09822j

data_7118177
_publ_section_title
;
 Divergent reactivity of an indole glucosinolate yields Lossen or Neber
 rearrangement products: the phytoalexin rapalexin A or a unique
 \b-d-glucopyranose fused heterocycle.
;
_journal_issue                   12
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2505
_journal_page_last               2508
_journal_paper_doi               10.1039/c5cc09822j
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C20 H26 N2 O6 S'
_chemical_formula_sum            'C20 H26 N2 O6 S'
_chemical_formula_weight         422.49
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           'manual editing of SHELXL-2014 template'
_audit_update_record
;
2015-11-27 deposited with the CCDC.
2015-12-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0216(5)
_cell_length_b                   21.3117(8)
_cell_length_c                   6.4976(2)
_cell_measurement_reflns_used    9987
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.805
_cell_measurement_theta_min      3.474
_cell_volume                     1941.64(12)
_computing_cell_refinement
' Saint V8.30A and SADABS V2012/1 (Apex2, v2013.10-0; Bruker AXS)'
_computing_data_collection
; <i>MXDC</i>, Macromolecular Crystallography Data Collector (Canadian
  Light Source, 2007)
;
_computing_data_reduction
' Saint V8.30A and SADABS V2012/1 (Apex2, v2013.10-0; Bruker AXS'
_computing_molecular_graphics    ' XP (SHELXTL-NT v6.14, Bruker AXS)'
_computing_publication_material  'enCIFer (v1.5.1), CCDC 2014'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    ' SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 13.8
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measurement_device_type
;
300mm 16K Rayonix MX300 HE CCD detector with
an ACCEL MD2 microdiffractometer
;
_diffrn_measurement_method       'CCD rotation images, \w scans'
_diffrn_radiation_monochromator  'double crystal Si(111)'
_diffrn_radiation_source         'Beamline 08B1-1 at the CLS'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.68879
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            59723
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_theta_full        24.411
_diffrn_reflns_theta_max         30.854
_diffrn_reflns_theta_min         1.685
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2012/1 (Apex2, Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_description       plate
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.781
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.18(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         5949
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0677P)^2^+0.9502P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1121
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.903
_reflns_number_gt                5880
_reflns_number_total             5949
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc09822j2.cif
_cod_data_source_block           compound15
_cod_depositor_comments          'Adding full bibliography for 7118177.cif.'
_cod_database_code               7118177
_shelx_estimated_absorpt_t_min   0.972
_shelx_estimated_absorpt_t_max   0.981
_shelxl_version_number           2014-3
_shelx_res_checksum              91529