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#$Date: 2016-03-21 02:22:01 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178384 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/06/4020661.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_4020661
loop_
_publ_author_name
'Kamyar Afarinkia'
'Akmal Bahar'
'Michael J. Bearpark'
'Yésica García-Ramos'
'Andrea Ruggiero'
'Judi Neuss'
'Maushami Vyas'
_publ_section_title
;
 Investigation of the Diels-Alder Cycloadditions of
 2(H)-1,4-Oxazin-2-ones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9529
_journal_page_last               9537
_journal_paper_doi               10.1021/jo051646i
_journal_volume                  70
_journal_year                    2005
_chemical_formula_sum            'C19 H13 Cl N2 O2'
_chemical_formula_weight         336.76
_chemical_name_common            arufrct2
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 96.706(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.0925(2)
_cell_length_b                   12.0434(6)
_cell_length_c                   21.4699(11)
_cell_measurement_temperature    120(2)
_cell_volume                     1564.56(12)
_diffrn_ambient_temperature      120(2)
_exptl_crystal_density_diffrn    1.430
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4020661
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Cl1 Cl 0.47932(10) 0.10444(5) 0.44819(3) 0.0252(3) Uani 1 1 d . . .
O1 O 0.7761(3) 0.36445(14) 0.52324(8) 0.0194(5) Uani 1 1 d . . .
O2 O 0.7244(3) 0.53868(16) 0.49225(8) 0.0217(5) Uani 1 1 d . . .
N1 N 0.5626(3) 0.30131(17) 0.40735(10) 0.0181(5) Uani 1 1 d . . .
N2 N 0.9557(4) 0.2454(2) 0.29864(12) 0.0369(7) Uani 1 1 d . . .
C1 C 0.7384(4) 0.4427(3) 0.47812(12) 0.0181(6) Uani 1 1 d . . .
C2 C 0.8070(4) 0.2514(2) 0.49987(12) 0.0185(6) Uani 1 1 d . . .
C3 C 1.0048(5) 0.2554(2) 0.46195(13) 0.0189(7) Uani 1 1 d . . .
H3A H 1.031(4) 0.181(2) 0.4463(11) 0.020(7) Uiso 1 1 d . . .
H3B H 1.138(4) 0.280(2) 0.4896(13) 0.030(8) Uiso 1 1 d . . .
C4 C 0.9555(4) 0.3400(2) 0.40827(12) 0.0183(7) Uani 1 1 d . . .
H4 H 1.069(4) 0.3965(18) 0.4133(10) 0.014(7) Uiso 1 1 d . . .
C5 C 0.7227(4) 0.3946(2) 0.41208(11) 0.0162(6) Uani 1 1 d . . .
C6 C 0.6115(4) 0.2314(2) 0.45043(12) 0.0171(6) Uani 1 1 d . . .
C7 C 0.9560(4) 0.2875(2) 0.34588(14) 0.0224(7) Uani 1 1 d . . .
C8 C 0.6631(4) 0.4816(2) 0.36208(12) 0.0186(7) Uani 1 1 d . . .
C9 C 0.4655(5) 0.4777(3) 0.32264(13) 0.0246(7) Uani 1 1 d . . .
H9 H 0.369(4) 0.417(2) 0.3255(11) 0.018(7) Uiso 1 1 d . . .
C10 C 0.4147(5) 0.5595(3) 0.27807(14) 0.0318(8) Uani 1 1 d . . .
H10 H 0.279(5) 0.555(2) 0.2516(13) 0.035(8) Uiso 1 1 d . . .
C11 C 0.5612(5) 0.6453(3) 0.27179(14) 0.0291(8) Uani 1 1 d . . .
H11 H 0.527(4) 0.698(2) 0.2398(13) 0.026(8) Uiso 1 1 d . . .
C12 C 0.7580(5) 0.6505(2) 0.31049(13) 0.0263(7) Uani 1 1 d . . .
H12 H 0.863(4) 0.713(2) 0.3055(13) 0.036(8) Uiso 1 1 d . . .
C13 C 0.8073(5) 0.5693(2) 0.35553(13) 0.0242(7) Uani 1 1 d . . .
H13 H 0.941(4) 0.5757(18) 0.3808(11) 0.013(7) Uiso 1 1 d . . .
C14 C 0.8309(4) 0.1784(2) 0.55728(12) 0.0194(7) Uani 1 1 d . . .
C15 C 0.6770(5) 0.1876(2) 0.60043(13) 0.0258(7) Uani 1 1 d . . .
H15 H 0.561(4) 0.2402(19) 0.5933(11) 0.019(7) Uiso 1 1 d . . .
C16 C 0.6961(5) 0.1231(2) 0.65384(14) 0.0294(8) Uani 1 1 d . . .
H16 H 0.588(4) 0.133(2) 0.6839(13) 0.032(8) Uiso 1 1 d . . .
C17 C 0.8688(5) 0.0485(2) 0.66546(14) 0.0295(8) Uani 1 1 d . . .
H17 H 0.878(4) 0.007(2) 0.7027(13) 0.028(8) Uiso 1 1 d . . .
C18 C 1.0223(5) 0.0391(2) 0.62349(13) 0.0267(7) Uani 1 1 d . . .
H18 H 1.148(5) -0.014(2) 0.6313(13) 0.041(9) Uiso 1 1 d . . .
C19 C 1.0036(5) 0.1028(2) 0.56960(13) 0.0230(7) Uani 1 1 d . . .
H19 H 1.109(4) 0.0964(18) 0.5407(11) 0.012(7) Uiso 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
Cl1 C6 1.727(3) . ?
O1 C1 1.352(3) . ?
O1 C2 1.471(3) . ?
O2 C1 1.200(3) . ?
N1 C6 1.260(3) . ?
N1 C5 1.483(3) . ?
N2 C7 1.134(3) . ?
C1 C5 1.524(4) . ?
C2 C14 1.507(4) . ?
C2 C6 1.519(4) . ?
C2 C3 1.532(4) . ?
C3 C4 1.542(4) . ?
C4 C7 1.482(4) . ?
C4 C5 1.574(3) . ?
C5 C8 1.513(3) . ?
C8 C9 1.389(4) . ?
C8 C13 1.392(4) . ?
C9 C10 1.383(4) . ?
C10 C11 1.382(4) . ?
C11 C12 1.378(4) . ?
C12 C13 1.384(4) . ?
C14 C19 1.394(4) . ?
C14 C15 1.397(4) . ?
C15 C16 1.379(4) . ?
C16 C17 1.384(4) . ?
C17 C18 1.377(4) . ?
C18 C19 1.382(4) . ?
