#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/07/4020784.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_4020784
loop_
_publ_author_name
'B. Jesse E. Reich'
'Aaron K. Justice'
'Brittany T. Beckstead'
'Joseph H. Reibenspies'
'Stephen A. Miller'
_publ_section_title
;
 Cyanide-Catalyzed Cyclizations via Aldimine Coupling
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1357
_journal_page_last               1359
_journal_paper_doi               10.1021/jo035245j
_journal_volume                  69
_journal_year                    2004
_chemical_formula_sum            'C16 H14 N2 O2'
_chemical_formula_weight         266.29
_chemical_name_common            sm08
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                101.721(2)
_cell_angle_beta                 98.011(2)
_cell_angle_gamma                99.562(2)
_cell_formula_units_Z            2
_cell_length_a                   5.8600(7)
_cell_length_b                   8.4944(10)
_cell_length_c                   13.4511(17)
_cell_measurement_temperature    110(2)
_cell_volume                     636.01(13)
_diffrn_ambient_temperature      110(2)
_exptl_crystal_density_diffrn    1.391
_cod_database_code               4020784
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
O1 O 0.03160(19) 1.07678(14) 0.13694(9) 0.0320(4) Uani 1 1 d . . .
H1 H 0.0534 0.9919 0.0981 0.048 Uiso 1 1 calc R . .
O2 O 1.0051(2) 0.66737(15) 0.22549(9) 0.0333(4) Uani 1 1 d . . .
H2 H 0.9248 0.6621 0.1677 0.050 Uiso 1 1 calc R . .
N1 N 0.2615(2) 0.85725(16) 0.06982(10) 0.0294(4) Uani 1 1 d . . .
N2 N 0.6623(2) 0.71583(16) 0.09823(10) 0.0276(4) Uani 1 1 d . . .
C1 C 0.4282(3) 1.07368(19) 0.21612(11) 0.0246(4) Uani 1 1 d . . .
C2 C 0.2328(3) 1.1508(2) 0.20420(12) 0.0265(4) Uani 1 1 d . . .
C3 C 0.2455(3) 1.3092(2) 0.26171(12) 0.0290(4) Uani 1 1 d . . .
H3 H 0.1126 1.3593 0.2551 0.035 Uiso 1 1 calc R . .
C4 C 0.4500(3) 1.3937(2) 0.32837(13) 0.0302(4) Uani 1 1 d . . .
H4 H 0.4569 1.5015 0.3675 0.036 Uiso 1 1 calc R . .
C5 C 0.6461(3) 1.32152(19) 0.33842(12) 0.0292(4) Uani 1 1 d . . .
H5 H 0.7875 1.3807 0.3832 0.035 Uiso 1 1 calc R . .
C6 C 0.6344(3) 1.16405(19) 0.28321(12) 0.0261(4) Uani 1 1 d . . .
H6 H 0.7688 1.1156 0.2907 0.031 Uiso 1 1 calc R . .
C7 C 0.4206(3) 0.90991(19) 0.15173(12) 0.0257(4) Uani 1 1 d . . .
C8 C 0.2840(3) 0.7096(2) -0.00324(13) 0.0336(4) Uani 1 1 d . . .
H8A H 0.1993 0.7060 -0.0730 0.040 Uiso 1 1 calc R . .
H8B H 0.2147 0.6104 0.0184 0.040 Uiso 1 1 calc R . .
C9 C 0.5417(3) 0.7143(2) -0.00530(12) 0.0321(4) Uani 1 1 d . . .
H9A H 0.5611 0.6170 -0.0556 0.038 Uiso 1 1 calc R . .
H9B H 0.6108 0.8139 -0.0268 0.038 Uiso 1 1 calc R . .
C10 C 0.5980(3) 0.80491(18) 0.17449(12) 0.0245(4) Uani 1 1 d . . .
C11 C 0.6900(3) 0.79662(18) 0.28032(12) 0.0238(4) Uani 1 1 d . . .
C12 C 0.5752(3) 0.84558(18) 0.36247(12) 0.0249(4) Uani 1 1 d . . .
H12 H 0.4349 0.8861 0.3495 0.030 Uiso 1 1 calc R . .
C13 C 0.6600(3) 0.83664(19) 0.46167(12) 0.0280(4) Uani 1 1 d . . .
H13 H 0.5782 0.8695 0.5161 0.034 Uiso 1 1 calc R . .
C14 C 0.8675(3) 0.7788(2) 0.48120(13) 0.0299(4) Uani 1 1 d . . .
H14 H 0.9301 0.7760 0.5497 0.036 Uiso 1 1 calc R . .
C15 C 0.9818(3) 0.72577(19) 0.40200(13) 0.0285(4) Uani 1 1 d . . .
H15 H 1.1225 0.6863 0.4162 0.034 Uiso 1 1 calc R . .
C16 C 0.8925(3) 0.72953(19) 0.30103(13) 0.0264(4) 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
O1 C2 1.352(2) . ?
O2 C16 1.3535(19) . ?
N1 C7 1.288(2) . ?
N1 C8 1.465(2) . ?
N2 C10 1.286(2) . ?
N2 C9 1.468(2) . ?
C1 C6 1.404(2) . ?
C1 C2 1.417(2) . ?
C1 C7 1.472(2) . ?
C2 C3 1.393(2) . ?
C3 C4 1.382(2) . ?
C4 C5 1.393(2) . ?
C5 C6 1.377(2) . ?
C7 C10 1.517(2) . ?
C8 C9 1.508(3) . ?
C10 C11 1.470(2) . ?
C11 C12 1.400(2) . ?
C11 C16 1.417(2) . ?
C12 C13 1.379(2) . ?
C13 C14 1.397(2) . ?
C14 C15 1.375(2) . ?
C15 C16 1.395(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21155403
2 PubChem 136636319
