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_4035566
_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      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-03
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2018.02.02 svn.r3482 for OlexSys, GUI svn.r5477)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.970(2)
_cell_length_b                   32.970(5)
_cell_length_c                   7.0999(11)
_cell_measurement_reflns_used    9978
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.704
_cell_measurement_theta_min      2.358
_cell_volume                     3270.1(8)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2014.11 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.37A (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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.495
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans with a narrow frame width'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            26194
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.745
_diffrn_reflns_theta_min         1.583
_diffrn_source                   'sealed tube'
_diffrn_source_current           1.4
_diffrn_source_voltage           50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1197 before and 0.0612 after correction. The Ratio of minimum to maximum transmission is 0.7864. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_description       plate
_exptl_crystal_F_000             1488
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of pentane and DCM  by vapor diffusion'
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         5076
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0652
_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^)+(0.0442P)^2^+6.8873P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1381
_refine_ls_wR_factor_ref         0.1468
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4071
_reflns_number_total             5076
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00812_si_003.cif
_cod_data_source_block           smhii-048c-f24-32
_cod_original_cell_volume        3270.1(9)
_cod_database_code               4035566
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.886
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All H(H) groups, All C(H) groups
2. Restrained distances
 C3-H3 = C10-H10C = C10-H10B = C10-H10A = C21-H21C = C21-H21B = C21-H21A
 0.999 with sigma of 0.005
 C19-H19 = C18-H18 = C17-H17 = C20-H20 = C9-H9 = C8-H8 = C7-H7 = C6-H6
 0.995 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Uiso(H9) = Uiso(H8) = Uiso(H7) = Uiso(H6)
Uiso(H10B) = Uiso(H10C) = Uiso(H10A) = Uiso(H21C) = Uiso(H21A) = Uiso(H21B)
;
_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-048C-F24-32
_olex2_submission_special_instructions 'No special instructions were received'