A synthetic route to 1,4-disubstituted tetrahydro-β-carbolines and tetrahydropyranoindoles via ring-opening/Pictet-Spengler reaction of aziridines and epoxides with indoles/aldehydes.
Wani, Imtiyaz Ahmad; Goswami, Gaurav; Sk, Sahid; Mal, Abhijit; Sayyad, Masthanvali; Ghorai, Manas K.; Organic & biomolecular chemistry 18 (2020) 272–287; doi:10.1039/c9ob02098e

data_7157299
_publ_section_title
;
 A synthetic route to 1,4-disubstituted tetrahydro-\b-carbolines and
 tetrahydropyranoindoles via ring-opening/Pictet-Spengler reaction of
 aziridines and epoxides with indoles/aldehydes.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              272
_journal_page_last               287
_journal_paper_doi               10.1039/c9ob02098e
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C31 H25 Br2 Cl N2 O2 S'
_chemical_formula_sum            'C31 H25 Br2 Cl N2 O2 S'
_chemical_formula_weight         684.86
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-29
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-07-10 deposited with the CCDC.	2019-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.562(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2533(9)
_cell_length_b                   29.303(2)
_cell_length_c                   10.6278(10)
_cell_measurement_reflns_used    7094
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.7
_cell_volume                     2856.1(4)
_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      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0688
_diffrn_reflns_av_unetI/netI     0.0745
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            28773
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.305
_diffrn_reflns_theta_min         2.683
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.037
_exptl_absorpt_correction_T_max  0.859
_exptl_absorpt_correction_T_min  0.539
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'whiteish white'
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_description       prism
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.760
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         7094
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0503
_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^)+(0.0420P)^2^+2.9990P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.1032
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5063
_reflns_number_total             7094
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob02098e2.cif
_cod_data_source_block           2octc_0m
_cod_depositor_comments
'Adding full bibliography for 7157299--7157300.cif.'
_cod_database_code               7157299
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.863
_shelx_estimated_absorpt_t_min   0.582
_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. Uiso/Uaniso restraints and constraints
Uanis(C00Y) \\sim Ueq, Uanis(C00S) \\sim Ueq, Uanis(C00Q) \\sim Ueq: with sigma
of 0.1 and sigma for terminal atoms of 0.2
Uanis(C00M) \\sim Ueq, Uanis(C00S) \\sim Ueq, Uanis(C00Y) \\sim Ueq,
Uanis(C00Q) \\sim Ueq, Uanis(C00H) \\sim Ueq, Uanis(C009) \\sim Ueq: with sigma
of 0.1 and sigma for terminal atoms of 0.2
Uanis(C00Y) = Uanis(C00S) = Uanis(C00Q)
3.a Ternary CH refined with riding coordinates:
 C00K(H00K), C00N(H00N)
3.b Secondary CH2 refined with riding coordinates:
 C00U(H00H,H00I)
3.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00C(H00C), C00F(H00F), C00G(H00G), C00M(H00M),
 C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00W(H00W), C00Z(H00Z),
 C010(H010), C011(H011), C013(H013)
3.d Idealised Me refined as rotating group:
 C00T(H00B,H00D,H00E), C012(H01A,H01B,H01C)
;
_shelx_res_checksum              63825
_shelx_hkl_checksum              44480
_olex2_submission_special_instructions 'No special instructions were received'