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#$Date: 2016-03-21 02:27:53 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178391 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/13/4021310.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_4021310
loop_
_publ_author_name
'Hongbin Li'
'Hua Yang'
'Jeffrey L. Petersen'
'Kung K. Wang'
_publ_section_title
;
 Biradicals/Zwitterions from Thermolysis of Enyne-Isocyanates.
 Application to the Synthesis of 2(1H)-Pyridones,
 Benzofuro[3,2-c]pyridin-1(2H)-ones,
 2,5-Dihydro-1H-pyrido[4,3-b]indol-1-ones, and Related Compounds.
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4500
_journal_page_last               4508
_journal_paper_doi               10.1021/jo049716t
_journal_volume                  69
_journal_year                    2004
_chemical_formula_sum            'C15 H14 N2 O'
_chemical_formula_weight         238.28
_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                 96.005(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9287(7)
_cell_length_b                   7.6930(7)
_cell_length_c                   19.2741(18)
_cell_measurement_temperature    295(2)
_cell_volume                     1169.18(18)
_diffrn_ambient_temperature      295(2)
_exptl_crystal_density_diffrn    1.354
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4021310
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
O1 O 0.59651(17) -0.38700(15) -0.06783(7) 0.0543(4) Uani 1 1 d . . .
N1 N 0.58714(18) -0.30916(17) 0.04607(7) 0.0415(4) Uani 1 1 d . . .
H1 H 0.5390 -0.4065 0.0537 0.050 Uiso 1 1 calc R . .
N2 N 0.81150(18) 0.15134(17) 0.00412(8) 0.0413(4) Uani 1 1 d . . .
C1 C 0.6167(2) -0.1955(2) 0.10038(9) 0.0377(4) Uani 1 1 d . A .
C2 C 0.5705(2) -0.2319(2) 0.17161(9) 0.0479(5) Uani 1 1 d . . .
H2A H 0.6171 -0.3420 0.1890 0.058 Uiso 1 1 calc R . .
H2B H 0.4484 -0.2336 0.1724 0.058 Uiso 1 1 calc R . .
C3 C 0.6508(3) -0.0793(2) 0.21432(10) 0.0551(5) Uani 1 1 d . . .
H3A H 0.7520 -0.1174 0.2429 0.066 Uiso 1 1 calc R . .
H3B H 0.5716 -0.0329 0.2447 0.066 Uiso 1 1 calc R . .
C4 C 0.6960(3) 0.0604(2) 0.16218(10) 0.0480(5) Uani 1 1 d . A .
H4A H 0.6144 0.1547 0.1594 0.058 Uiso 1 1 calc R . .
H4B H 0.8084 0.1072 0.1753 0.058 Uiso 1 1 calc R . .
C5 C 0.6891(2) -0.0366(2) 0.09410(9) 0.0379(4) Uani 1 1 d . . .
C6 C 0.7366(2) 0.00384(19) 0.02749(9) 0.0359(4) Uani 1 1 d . A .
C7 C 0.7111(2) -0.11422(19) -0.02796(9) 0.0369(4) Uani 1 1 d . . .
C8 C 0.6298(2) -0.2771(2) -0.02020(9) 0.0399(4) Uani 1 1 d . A .
C9 C 0.7733(2) -0.0359(2) -0.08767(9) 0.0384(4) Uani 1 1 d . A .
C10 C 0.7820(2) -0.0870(2) -0.15658(10) 0.0484(5) Uani 1 1 d . . .
H10 H 0.7437 -0.1961 -0.1719 0.058 Uiso 1 1 calc R A .
C11 C 0.8487(3) 0.0275(3) -0.20185(11) 0.0560(5) Uani 1 1 d . A .
H11 H 0.8542 -0.0047 -0.2481 0.067 Uiso 1 1 calc R . .
C12 C 0.9076(3) 0.1907(3) -0.17905(11) 0.0580(6) Uani 1 1 d . . .
H12 H 0.9517 0.2653 -0.2105 0.070 Uiso 1 1 calc R A .
C13 C 0.9023(2) 0.2443(2) -0.11106(11) 0.0512(5) Uani 1 1 d . A .
H13 H 0.9424 0.3530 -0.0961 0.061 Uiso 1 1 calc R . .
C14 C 0.8345(2) 0.1295(2) -0.06591(10) 0.0411(4) Uani 1 1 d . A .
C15 C 0.8565(3) 0.3083(2) 0.04383(11) 0.0537(5) Uani 0.70(3) 1 d P A 1
H15A H 0.8008 0.3083 0.0857 0.081 Uiso 0.70(3) 1 calc PR A 1
H15B H 0.8215 0.4083 0.0162 0.081 Uiso 0.70(3) 1 calc PR A 1
H15C H 0.9771 0.3118 0.0558 0.081 Uiso 0.70(3) 1 calc PR A 1
C15' C 0.8565(3) 0.3083(2) 0.04383(11) 0.0537(5) Uani 0.30(3) 1 d P A 2
H15D H 0.9279 0.2786 0.0855 0.081 Uiso 0.30(3) 1 calc PR A 2
H15E H 0.7554 0.3637 0.0562 0.081 Uiso 0.30(3) 1 calc PR A 2
H15F H 0.9161 0.3862 0.0161 0.081 Uiso 0.30(3) 1 calc PR A 2
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 C8 1.2558(19) . ?
N1 C1 1.365(2) . ?
N1 C8 1.378(2) . ?
N2 C6 1.378(2) . ?
N2 C14 1.391(2) . ?
N2 C15 1.454(2) . ?
C1 C5 1.362(2) . ?
C1 C2 1.484(2) . ?
C2 C3 1.533(3) . ?
C3 C4 1.539(3) . ?
C4 C5 1.505(2) . ?
C5 C6 1.410(2) . ?
C6 C7 1.401(2) . ?
C7 C8 1.424(2) . ?
C7 C9 1.431(2) . ?
C9 C10 1.394(3) . ?
C9 C14 1.410(2) . ?
C10 C11 1.383(3) . ?
C11 C12 1.394(3) . ?
C12 C13 1.379(3) . ?
C13 C14 1.387(3) . ?
