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_7157300
_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         'C24 H19 Br2 N O'
_chemical_formula_sum            'C24 H19 Br2 N O'
_chemical_formula_weight         497.22
_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     dual
_audit_creation_date             2018-06-29
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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
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_cell_length_b                   13.464(4)
_cell_length_c                   20.373(7)
_cell_measurement_reflns_used    3680
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_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 0.989
_diffrn_measured_fraction_theta_max 0.986
_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  0.0915
_diffrn_reflns_av_unetI/netI     0.0974
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
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_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.278
_diffrn_reflns_theta_min         2.025
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.969
_exptl_absorpt_correction_T_max  0.820
_exptl_absorpt_correction_T_min  0.448
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            WHITE
_exptl_crystal_density_diffrn    1.611
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_exptl_crystal_F_000             992
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_R_factor_gt           0.0805
_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^)+(0.0770P)^2^+13.6120P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1836
_refine_ls_wR_factor_ref         0.2111
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2175
_reflns_number_total             3680
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob02098e2.cif
_cod_data_source_block           5deca_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Empirical' was
changed to 'empirical' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7157299--7157300.cif.
;
_cod_original_cell_volume        2050.0(12)
_cod_database_code               7157300
_shelx_shelxl_version_number     2016/6
_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 Ternary CH refined with riding coordinates:
 C006(H006), C00F(H00F)
2.b Secondary CH2 refined with riding coordinates:
 C00M(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00G(H00G), C00I(H00I), C00J(H00J), C00K(H00K),
 C00L(H00L), C00N(H00N), C00O(H00O), C00Q(H00Q), C00R(H00R), C00S(H00S)
2.d Idealised Me refined as rotating group:
 C00P(H00C,H00H,H00M)
;
_shelx_res_checksum              91120
_shelx_hkl_checksum              46437
_olex2_submission_special_instructions 'No special instructions were received'