Dual vicinal functionalisation of heterocycles <i>via</i> an interrupted Pummerer coupling/[3,3]-sigmatropic rearrangement cascade.
Šiaučiulis, Mindaugas; Sapmaz, Selma; Pulis, Alexander P.; Procter, David J.; Chemical science 9 (2018) 754–759; doi:10.1039/c7sc04723a

data_1548111
_publ_section_title
;
 Dual vicinal functionalisation of heterocycles <i>via</i> an interrupted
 Pummerer coupling/[3,3]-sigmatropic rearrangement cascade.
;
_journal_issue                   3
_journal_name_full               'Chemical science'
_journal_page_first              754
_journal_page_last               759
_journal_paper_doi               10.1039/c7sc04723a
_journal_volume                  9
_journal_year                    2018
_chemical_formula_moiety         'C15 H17 N O S'
_chemical_formula_sum            'C15 H17 N O S'
_chemical_formula_weight         259.35
_chemical_name_systematic        2-Allyl-3-(allylsulfinyl)-1-methyl-1H-indole
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-08-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-08-24 deposited with the CCDC.
2017-11-17 downloaded from the CCDC.
;
_cell_angle_alpha                104.937(5)
_cell_angle_beta                 100.291(5)
_cell_angle_gamma                100.461(5)
_cell_formula_units_Z            2
_cell_length_a                   8.2973(5)
_cell_length_b                   9.1320(6)
_cell_length_c                   9.7066(5)
_cell_measurement_reflns_used    2819
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.2800
_cell_measurement_theta_min      4.3850
_cell_volume                     678.86(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1636
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -17.00  79.00   1.00    1.00    --   11.69  57.00 -90.00   96
  2  \w    -16.00  71.00   1.00    1.00    --   11.69  77.00  30.00   87
  3  \w    -60.00  33.00   1.00    1.00    --   11.69 -57.00 120.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0527020000
_diffrn_orient_matrix_UB_12      0.0164039000
_diffrn_orient_matrix_UB_13      0.0709267000
_diffrn_orient_matrix_UB_21      0.0395682000
_diffrn_orient_matrix_UB_22      -0.0602305000
_diffrn_orient_matrix_UB_23      -0.0275945000
_diffrn_orient_matrix_UB_31      0.0605360000
_diffrn_orient_matrix_UB_32      0.0543909000
_diffrn_orient_matrix_UB_33      -0.0164037000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4526
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         3.721
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.27b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.42676
_exptl_crystal_size_mid          0.27785
_exptl_crystal_size_min          0.22233
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2471
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0366
_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^)+(0.0424P)^2^+0.1692P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0942
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2102
_reflns_number_total             2471
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc04723a2.cif
_cod_data_source_block           odjp11
_cod_depositor_comments
'Adding full bibliography for 1548110--1548111.cif.'
_cod_original_cell_volume        678.86(7)
_cod_database_code               1548111
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         C15H17NSO
_reflns_odcompleteness_completeness 99.14
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B), C00C(H00D,H00E)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00B(H00C), C00D(H00F), C00F(H00J), C00G(H00K)
2.c Idealised Me refined as rotating group:
 C00E(H00G,H00H,H00I)
;
_shelx_res_checksum              66396
_olex2_date_sample_data_collection 2017-06-07
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.337
_oxdiff_exptl_absorpt_empirical_full_min 0.736