#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/09/4020968.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4020968
loop_
_publ_author_name
'Rosa L. Meza-León'
'David Crich'
'Sylvain Bernès'
'Leticia Quintero'
_publ_section_title
;
 Endo-Selective Quenching of Hexahydropyrrolo[2,3-b]indole-Based
 N-Acyliminium Ions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3976
_journal_page_last               3978
_journal_paper_doi               10.1021/jo049757p
_journal_volume                  69
_journal_year                    2004
_chemical_formula_sum            'C21 H22 N2 O4 S'
_chemical_formula_weight         398.47
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5090(7)
_cell_length_b                   11.5930(8)
_cell_length_c                   20.2321(13)
_cell_measurement_temperature    298(2)
_cell_volume                     1995.8(2)
_diffrn_ambient_temperature      298(2)
_exptl_crystal_density_diffrn    1.326
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4020968
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.94180(8) 0.54752(6) 0.08842(3) 0.05450(19) Uani 1 1 d . . .
N1 N 1.3454(2) 0.45189(17) 0.14714(10) 0.0509(5) Uani 1 1 d . . .
C2 C 1.4548(3) 0.4787(2) 0.20097(11) 0.0522(6) Uani 1 1 d . . .
H2A H 1.5589 0.4483 0.1898 0.063 Uiso 1 1 calc R . .
C3 C 1.4600(3) 0.6107(2) 0.19896(13) 0.0563(6) Uani 1 1 d . . .
H3A H 1.4780 0.6420 0.2428 0.068 Uiso 1 1 calc R . .
H3B H 1.5429 0.6372 0.1698 0.068 Uiso 1 1 calc R . .
C3A C 1.2992(3) 0.6473(2) 0.17289(12) 0.0494(6) Uani 1 1 d . . .
H3AA H 1.3069 0.7188 0.1473 0.059 Uiso 1 1 calc R . .
C3B C 1.1717(3) 0.6558(2) 0.22464(12) 0.0498(6) Uani 1 1 d . . .
C4 C 1.1673(4) 0.7208(2) 0.28227(14) 0.0644(7) Uani 1 1 d . . .
H4A H 1.2514 0.7678 0.2940 0.077 Uiso 1 1 calc R . .
C5 C 1.0346(4) 0.7141(3) 0.32186(14) 0.0757(8) Uani 1 1 d . . .
H5A H 1.0282 0.7594 0.3597 0.091 Uiso 1 1 calc R . .
C6 C 0.9126(4) 0.6419(3) 0.30615(14) 0.0722(8) Uani 1 1 d . . .
H6A H 0.8254 0.6384 0.3338 0.087 Uiso 1 1 calc R . .
C7 C 0.9168(3) 0.5741(3) 0.24995(12) 0.0621(7) Uani 1 1 d . . .
H7A H 0.8353 0.5236 0.2398 0.075 Uiso 1 1 calc R . .
C7A C 1.0479(3) 0.5842(2) 0.20901(11) 0.0487(6) Uani 1 1 d . . .
N8 N 1.0744(2) 0.52510(16) 0.14728(9) 0.0464(5) Uani 1 1 d . . .
C8A C 1.2430(3) 0.5462(2) 0.12899(11) 0.0465(5) Uani 1 1 d . . .
H8AA H 1.2534 0.5651 0.0820 0.056 Uiso 1 1 calc R . .
C9 C 1.3669(3) 0.3548(2) 0.11086(14) 0.0599(7) Uani 1 1 d . . .
O10 O 1.4603(3) 0.27998(17) 0.12422(11) 0.0813(6) Uani 1 1 d . . .
O11 O 1.2718(2) 0.35322(17) 0.05835(10) 0.0725(6) Uani 1 1 d . . .
C12 C 1.2818(4) 0.2544(3) 0.01575(18) 0.0927(11) Uani 1 1 d . . .
H12A H 1.2086 0.2628 -0.0200 0.139 Uiso 1 1 calc R . .
H12B H 1.2570 0.1860 0.0404 0.139 Uiso 1 1 calc R . .
H12C H 1.3865 0.2483 -0.0016 0.139 Uiso 1 1 calc R . .
C13 C 1.4023(3) 0.4272(2) 0.26648(13) 0.0655(7) Uani 1 1 d . . .
H13A H 1.3084 0.4666 0.2816 0.079 Uiso 1 1 calc R . .
H13B H 1.3765 0.3464 0.2602 0.079 Uiso 1 1 calc R . .
C14 C 1.5265(5) 0.4376(3) 0.31722(16) 0.0885(10) Uani 1 1 d . . .
H14A H 1.6202 0.3993 0.3083 0.106 Uiso 1 1 calc R . .
C15 C 1.5209(6) 0.4923(4) 0.37128(18) 0.1214(16) Uani 1 1 d . . .
H15A H 1.4303 0.5324 0.3829 0.146 Uiso 1 1 calc R . .
H15B H 1.6074 0.4926 0.3994 0.146 Uiso 1 1 calc R . .
O16 O 0.79162(18) 0.52805(18) 0.11829(10) 0.0690(5) Uani 1 1 d . . .
O17 O 0.9882(2) 0.48185(17) 0.03256(9) 0.0724(6) Uani 1 1 d . . .
C18 C 0.9577(3) 0.6946(2) 0.06782(11) 0.0510(6) Uani 1 1 d . . .
C19 C 1.0328(3) 0.7267(3) 0.01042(13) 0.0662(8) Uani 1 1 d . . .
H19A H 1.0717 0.6708 -0.0182 0.079 Uiso 1 1 calc R . .
C19' C 0.8976(3) 0.7775(2) 0.11038(14) 0.0649(7) Uani 1 1 d . . .
H19B H 0.8447 0.7555 0.1486 0.078 Uiso 1 1 calc R . .
C20 C 1.0501(4) 0.8424(3) -0.00435(16) 0.0831(9) Uani 1 1 d . . .
H20A H 1.1004 0.8647 -0.0431 0.100 Uiso 1 1 calc R . .
C20' C 0.9169(4) 0.8920(3) 0.09555(17) 0.0827(9) Uani 1 1 d . . .
H20B H 0.8787 0.9481 0.1242 0.099 Uiso 1 1 calc R . .
C21 C 0.9930(4) 0.9242(3) 0.03811(18) 0.0844(10) Uani 1 1 d . . .
H21A H 1.0055 1.0020 0.0282 0.101 Uiso 1 1 calc R . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O17 1.4187(18) . ?
S1 O16 1.4315(18) . ?
S1 N8 1.6609(19) . ?
S1 C18 1.761(3) . ?
N1 C9 1.357(3) . ?
N1 C8A 1.446(3) . ?
N1 C2 1.466(3) . ?
C2 C13 1.521(3) . ?
C2 C3 1.532(3) . ?
C3 C3A 1.526(4) . ?
C3A C3B 1.511(4) . ?
C3A C8A 1.546(3) . ?
C3B C7A 1.378(4) . ?
C3B C4 1.389(4) . ?
C4 C5 1.387(4) . ?
C5 C6 1.371(4) . ?
C6 C7 1.383(4) . ?
C7 C7A 1.395(3) . ?
C7A N8 1.442(3) . ?
N8 C8A 1.502(3) . ?
C9 O10 1.207(3) . ?
C9 O11 1.336(3) . ?
O11 C12 1.436(4) . ?
C13 C14 1.478(4) . ?
C14 C15 1.266(5) . ?
C18 C19 1.377(3) . ?
C18 C19' 1.388(3) . ?
C19 C20 1.383(5) . ?
C19' C20' 1.371(4) . ?
C20 C21 1.368(5) . ?
C20' C21 1.382(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9581768
2 PubChem 11406873
