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#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/12/4021261.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_4021261
loop_
_publ_author_name
'Alexis D. C. Parenty'
'Louise V. Smith'
'Alexandra L. Pickering'
'De-Liang Long'
'Leroy Cronin'
_publ_section_title
;
 General One-Pot, Three-Step Methodology Leading to
 an Extended Class of N-Heterocyclic Cations:
 Spontaneous Nucleophilic Addition, Cyclization, and Hydride Loss
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5934
_journal_page_last               5946
_journal_paper_doi               10.1021/jo0495440
_journal_volume                  69
_journal_year                    2004
_chemical_formula_moiety         '(C22 H19 N2 O +), (Br -)'
_chemical_formula_sum            'C22 H19 Br N2 O'
_chemical_formula_weight         407.30
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 106.3650(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.48210(10)
_cell_length_b                   14.2325(2)
_cell_length_c                   12.5420(2)
_cell_measurement_temperature    150(2)
_cell_volume                     1795.29(4)
_diffrn_ambient_temperature      150(2)
_exptl_crystal_density_diffrn    1.507
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4021261
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
C11 C 0.07060(18) 0.38537(14) 0.58331(15) 0.0217(4) Uani 1 1 d . . .
C12 C 0.1013(2) 0.31257(15) 0.51922(16) 0.0282(4) Uani 1 1 d . . .
H12 H 0.0452 0.2592 0.5001 0.034 Uiso 1 1 calc R . .
C13 C 0.2148(2) 0.32010(16) 0.48450(17) 0.0338(5) Uani 1 1 d . . .
H13 H 0.2370 0.2712 0.4413 0.041 Uiso 1 1 calc R . .
C14 C 0.2969(2) 0.39805(17) 0.51176(17) 0.0341(5) Uani 1 1 d . . .
H14 H 0.3752 0.4016 0.4880 0.041 Uiso 1 1 calc R . .
C15 C 0.2655(2) 0.47069(16) 0.57329(16) 0.0303(5) Uani 1 1 d . . .
H15 H 0.3217 0.5242 0.5904 0.036 Uiso 1 1 calc R . .
C16 C 0.15046(18) 0.46586(14) 0.61087(15) 0.0225(4) Uani 1 1 d . . .
C21 C 0.00104(18) 0.52704(13) 0.71902(15) 0.0195(4) Uani 1 1 d . . .
C22 C -0.03210(19) 0.59807(13) 0.78519(16) 0.0241(4) Uani 1 1 d . . .
H22 H -0.1080 0.5907 0.8117 0.029 Uiso 1 1 calc R . .
C23 C 0.0444(2) 0.67779(14) 0.81167(16) 0.0270(4) Uani 1 1 d . . .
H23 H 0.0223 0.7247 0.8574 0.032 Uiso 1 1 calc R . .
C24 C 0.1541(2) 0.68973(14) 0.77133(16) 0.0278(4) Uani 1 1 d . . .
H24 H 0.2066 0.7450 0.7896 0.033 Uiso 1 1 calc R . .
C25 C 0.18748(19) 0.62236(14) 0.70536(16) 0.0258(4) Uani 1 1 d . . .
H25 H 0.2619 0.6323 0.6776 0.031 Uiso 1 1 calc R . .
C26 C 0.11365(18) 0.53909(13) 0.67820(15) 0.0212(4) Uani 1 1 d . . .
C31 C -0.2270(2) 0.31908(14) 0.66917(17) 0.0269(4) Uani 1 1 d . . .
H31A H -0.3189 0.3227 0.6197 0.032 Uiso 1 1 calc R . .
H31B H -0.2234 0.2718 0.7278 0.032 Uiso 1 1 calc R . .
C32 C -0.1289(2) 0.29551(14) 0.60388(17) 0.0260(4) Uani 1 1 d . . .
H32A H -0.0787 0.2375 0.6323 0.031 Uiso 1 1 calc R . .
H32B H -0.1749 0.2875 0.5239 0.031 Uiso 1 1 calc R . .
C33 C -0.07437(17) 0.44107(13) 0.68971(14) 0.0191(4) Uani 1 1 d . . .
C41 C -0.24325(18) 0.45473(13) 0.79398(15) 0.0208(4) Uani 1 1 d . . .
C42 C -0.18873(19) 0.44337(14) 0.90732(16) 0.0246(4) Uani 1 1 d . . .
H42 H -0.1129 0.4045 0.9349 0.030 Uiso 1 1 calc R . .
C43 C -0.24574(19) 0.48916(14) 0.98048(16) 0.0251(4) Uani 1 1 d . . .
H43 H -0.2084 0.4823 1.0584 0.030 Uiso 1 1 calc R . .
C44 C -0.35754(18) 0.54500(13) 0.93919(15) 0.0213(4) Uani 1 1 d . . .
C45 C -0.41398(18) 0.55345(14) 0.82472(16) 0.0236(4) Uani 1 1 d . . .
H45 H -0.4919 0.5902 0.7967 0.028 Uiso 1 1 calc R . .
C46 C -0.35682(18) 0.50854(14) 0.75227(16) 0.0236(4) Uani 1 1 d . . .
H46 H -0.3949 0.5144 0.6743 0.028 Uiso 1 1 calc R . .
C47 C -0.3581(2) 0.59435(15) 1.12071(16) 0.0305(5) Uani 1 1 d . . .
H47A H -0.4118 0.6315 1.1578 0.046 Uiso 1 1 calc R . .
H47B H -0.2691 0.6219 1.1360 0.046 Uiso 1 1 calc R . .
H47C H -0.3509 0.5297 1.1487 0.046 Uiso 1 1 calc R . .
N1 N -0.04048(15) 0.37806(11) 0.62293(12) 0.0205(3) Uani 1 1 d . . .
N2 N -0.18097(15) 0.41181(11) 0.71797(13) 0.0219(3) Uani 1 1 d . . .
O O -0.42012(13) 0.59415(9) 1.00344(11) 0.0261(3) Uani 1 1 d . . .
Br Br 0.452251(19) 0.737615(14) 0.603875(16) 0.02795(7) Uani 1 1 d . . .
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
C11 N1 1.393(2) . ?
C11 C12 1.403(3) . ?
C11 C16 1.403(3) . ?
C12 C13 1.382(3) . ?
C13 C14 1.386(3) . ?
C14 C15 1.384(3) . ?
C15 C16 1.415(3) . ?
C16 C26 1.460(3) . ?
C21 C22 1.412(3) . ?
C21 C26 1.423(3) . ?
C21 C33 1.447(3) . ?
C22 C23 1.375(3) . ?
C23 C24 1.392(3) . ?
C24 C25 1.375(3) . ?
C25 C26 1.404(3) . ?
C31 N2 1.477(2) . ?
C31 C32 1.521(3) . ?
C32 N1 1.474(2) . ?
C33 N2 1.331(2) . ?
C33 N1 1.341(2) . ?
C41 C42 1.384(3) . ?
C41 C46 1.388(3) . ?
C41 N2 1.435(2) . ?
C42 C43 1.390(3) . ?
C43 C44 1.390(3) . ?
C44 O 1.366(2) . ?
C44 C45 1.395(3) . ?
C45 C46 1.378(3) . ?
C47 O 1.431(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9467679
