#------------------------------------------------------------------------------
#$Date: 2015-01-27 21:58:39 +0200 (Tue, 27 Jan 2015) $
#$Revision: 130149 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/13/4021309.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_4021309
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            'C16 H16 N2 O'
_chemical_formula_weight         252.31
_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                113.440(10)
_cell_angle_beta                 105.85(2)
_cell_angle_gamma                99.42(2)
_cell_formula_units_Z            2
_cell_length_a                   7.4460(10)
_cell_length_b                   9.579(2)
_cell_length_c                   10.5460(10)
_cell_measurement_temperature    293(2)
_cell_volume                     631.5(2)
_diffrn_ambient_temperature      293(2)
_exptl_crystal_density_diffrn    1.327
_refine_ls_R_factor_obs          0.0451
_refine_ls_wR_factor_obs         0.1082
_cod_database_code               4021309
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
O O -0.2366(3) 0.3659(2) 0.4040(2) 0.0554(5) Uani 1 d . .
N1 N -0.2579(3) 0.1382(2) 0.4347(2) 0.0461(5) Uani 1 d . .
N2 N -0.2566(3) -0.0834(2) 0.0069(2) 0.0415(5) Uani 1 d . .
C1 C -0.2686(3) -0.0188(3) 0.3734(2) 0.0442(6) Uani 1 d . .
C2 C -0.2804(4) -0.1147(3) 0.4552(3) 0.0551(7) Uani 1 d . .
H2A H -0.3922(4) -0.1124(3) 0.4855(3) 0.066 Uiso 1 calc R .
H2B H -0.1618(4) -0.0740(3) 0.5429(3) 0.066 Uiso 1 calc R .
C3 C -0.3037(5) -0.2828(3) 0.3432(3) 0.0781(9) Uani 1 d . .
H3A H -0.4330(5) -0.3533(3) 0.3146(3) 0.094 Uiso 1 calc R .
H3B H -0.2065(5) -0.3233(3) 0.3871(3) 0.094 Uiso 1 calc R .
C4 C -0.2769(4) -0.2778(3) 0.2069(3) 0.0519(7) Uani 1 d . .
H4A H -0.1566(4) -0.2996(3) 0.1988(3) 0.062 Uiso 1 calc R .
H4B H -0.3867(4) -0.3550(3) 0.1164(3) 0.062 Uiso 1 calc R .
C5 C -0.2673(3) -0.1090(3) 0.2349(2) 0.0412(6) Uani 1 d . .
C6 C -0.2566(3) -0.0303(3) 0.1495(2) 0.0403(6) Uani 1 d . .
C7 C -0.2428(3) 0.0433(3) -0.0258(2) 0.0413(6) Uani 1 d . .
C8 C -0.2374(3) 0.0466(3) -0.1552(3) 0.0491(6) Uani 1 d . .
H9A H -0.2435(3) -0.0448(3) -0.2358(3) 0.059 Uiso 1 calc R .
C9 C -0.2228(4) 0.1884(3) -0.1608(3) 0.0542(7) Uani 1 d . .
H9A H -0.2200(4) 0.1928(3) -0.2468(3) 0.065 Uiso 1 calc R .
C10 C -0.2121(4) 0.3261(3) -0.0402(3) 0.0538(7) Uani 1 d . .
H10A H -0.2005(4) 0.4210(3) -0.0467(3) 0.065 Uiso 1 calc R .
C11 C -0.2183(3) 0.3246(3) 0.0886(3) 0.0476(6) Uani 1 d . .
H11A H -0.2127(3) 0.4169(3) 0.1681(3) 0.057 Uiso 1 calc R .
C12 C -0.2333(3) 0.1818(3) 0.0974(2) 0.0402(5) Uani 1 d . .
C13 C -0.2430(3) 0.1328(3) 0.2090(2) 0.0397(5) Uani 1 d . .
C14 C -0.2462(3) 0.2086(3) 0.3518(2) 0.0426(6) Uani 1 d . .
C15 C -0.2778(4) -0.2443(3) -0.0974(3) 0.0520(6) Uani 1 d . .
H15A H -0.2343(101) -0.3010(27) -0.0438(4) 0.062 Uiso 0.53(5) calc PR 1
H15B H -0.2001(85) -0.2405(3) -0.1558(56) 0.062 Uiso 0.53(5) calc PR 1
H15C H -0.4132(17) -0.2984(29) -0.1619(53) 0.062 Uiso 0.53(5) calc PR 1
H15D H -0.1509(11) -0.2538(24) -0.0957(60) 0.062 Uiso 0.47(5) calc PR 2
H15E H -0.3587(89) -0.2675(31) -0.1959(12) 0.062 Uiso 0.47(5) calc PR 2
H15F H -0.3380(98) -0.3186(7) -0.0700(47) 0.062 Uiso 0.47(5) calc PR 2
C16 C -0.2383(5) 0.4468(3) 0.5502(3) 0.0691(8) Uani 1 d . .
H16A H -0.2157(25) 0.5586(5) 0.5791(8) 0.083 Uiso 1 calc R .
H16B H -0.1369(16) 0.4335(17) 0.6193(4) 0.083 Uiso 1 calc R .
H16C H -0.3635(9) 0.4026(14) 0.5505(5) 0.083 Uiso 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
O C14 1.364(3) . ?
O C16 1.429(3) . ?
N1 C14 1.311(3) . ?
N1 C1 1.358(3) . ?
N2 C7 1.383(3) . ?
N2 C6 1.383(3) . ?
N2 C15 1.445(3) . ?
C1 C5 1.373(3) . ?
C1 C2 1.497(3) . ?
C2 C3 1.517(4) . ?
C3 C4 1.523(4) . ?
C4 C5 1.509(3) . ?
C5 C6 1.395(3) . ?
C6 C13 1.407(3) . ?
C7 C8 1.389(3) . ?
C7 C12 1.414(3) . ?
C8 C9 1.371(3) . ?
C9 C10 1.393(4) . ?
C10 C11 1.377(3) . ?
C11 C12 1.396(3) . ?
C12 C13 1.444(3) . ?
C13 C14 1.397(3) . ?
