Synthesis of [3a,7a]-Dihydroindoles by a Tandem Arene Cyclopropanation/3,5-Sigmatropic Rearrangement Reaction.
Wilkerson-Hill, Sidney M; Haines, Brandon E.; Musaev, Djamaladdin G.; Davies, Huw M. L.; The Journal of organic chemistry 83 (2018) 7939–7949; doi:10.1021/acs.joc.8b00812

data_4035567
_publ_section_title
;
 Synthesis of [3a,7a]-Dihydroindoles by a Tandem Arene
 Cyclopropanation/3,5-Sigmatropic Rearrangement Reaction.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7939
_journal_page_last               7949
_journal_paper_doi               10.1021/acs.joc.8b00812
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C18 H16 N2 O4 S'
_chemical_formula_sum            'C18 H16 N2 O4 S'
_chemical_formula_weight         356.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-12-13
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2017.11.20 svn.r3469 for OlexSys, GUI svn.r5431)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.125(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6732(14)
_cell_length_b                   16.353(4)
_cell_length_c                   17.767(4)
_cell_measurement_reflns_used    7257
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.59
_cell_measurement_theta_min      2.49
_cell_volume                     1648.3(7)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2014.11 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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-2014/4 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker D8 diffractometer with APEX2 detector'
_diffrn_measurement_method       '\f and \w scans with a narrow frame width'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13880
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.602
_diffrn_reflns_theta_min         1.245
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           35
_diffrn_source_voltage           45
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5035
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1583 before and 0.0588 after correction. The Ratio of minimum to maximum transmission is 0.6748. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_recrystallization_method 'vapor diffusion pentanes into DCM'
_exptl_crystal_size_max          0.982
_exptl_crystal_size_mid          0.492
_exptl_crystal_size_min          0.174
_refine_diff_density_max         0.691
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.150
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4913
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0635
_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^)+(0.0588P)^2^+1.7037P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1349
_refine_ls_wR_factor_ref         0.1443
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4112
_reflns_number_total             4913
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00812_si_004.cif
_cod_data_source_block           smhii-o48c-lrf-meohp
_cod_database_code               4035567
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.811
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.1579(12)
 0.8421(12)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C3(H3), C2(H2)
3.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C5(H5), C17(H17), C18(H18), C20(H20), C9(H9), C8(H8), C6(H6)
3.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              43478
_shelx_hkl_checksum              30764
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a loop with paratone oil'
_olex2_submission_original_sample_id SMHII-O48C-LrF-MeOHp
_olex2_submission_special_instructions 'No special instructions were received'