data_2010188
_journal_name_full  'Acta Crystallographica'
_journal_year  1994
_journal_volume  C50
_journal_page_first  1772
_journal_page_last  1774
_publ_section_title
;
3'-(2,6-Dichlorophenyl)bicyclo
[2.2.1]heptane-2-spiro-5'(4'H)-isoxazole-3-one
;
loop_
_publ_author_name
  'Mackay, M. F.'
  'Savage, G. P.'
  'Simpson, G.W.'
_chemical_formula_moiety  'C15 H13 Cl2 N1 O2'
_chemical_formula_sum  'C15 H13 Cl2 N1 O2'
_chemical_formula_weight  310.2
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
loop_
_symmetry_equiv_pos_as_xyz
  'x,y,z'
  '-x,-y,-z'
  '-x,1/2+y,1/2-z'
  'x,1/2-y,1/2+z'
_cell_length_a  7.2610(10)
_cell_length_b  16.913(2)
_cell_length_c  11.5740(10)
_cell_angle_alpha  90.0
_cell_angle_beta  94.850(10)
_cell_angle_gamma  90.0
_cell_volume  1416.3(5)
_cell_formula_units_Z  4
_cell_measurement_temperature  291.0(10)
_exptl_crystal_density_diffrn  1.454
_exptl_crystal_density_meas  1.450(5)
_diffrn_ambient_temperature  291.0(10)
_refine_ls_R_factor_obs  .046
_refine_ls_wR_factor_obs  .066
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
  C1 0.2177(6) 0.1990(2) 0.9675(4)
  C2 0.1581(5) 0.1276(2) 0.8919(3)
  C3 -0.0271(5) 0.1068(2) 0.9404(3)
  O3 -0.1219(4) 0.05000(10)
  0.9115(2)
  C4 -0.0628(6) 0.1701(2) 1.0257(4)
  C5 0.0699(6) 0.1509(3) 1.1339(4)
  C6 0.2610(6) 0.1701(3) 1.0925(4)
  C7 0.0330(6) 0.2407(2) 0.9750(5)
  O1' 0.1074(3) 0.15480(10)
  0.7725(2)
  N2' 0.2302(4) 0.1220(2) 0.6976(2)
  C3' 0.3350(4) 0.0724(2) 0.7535(3)
  C4' 0.2960(6) 0.0618(2) 0.8772(3)
  C1'' 0.4862(4) 0.0354(2) 0.6960(3)
  C2'' 0.4858(5) -0.0446(2) 0.6664(3)
  C3'' 0.6290(6) -0.0791(2) 0.6126(4)
  C4'' 0.7786(6) -0.0334(3) 0.5892(4)
  C5'' 0.7853(5) 0.0456(3) 0.6174(4)
  C6'' 0.6406(4) 0.0788(2) 0.6691(3)
  Cl2'' 0.29790(10)
  -0.10210(10)
  0.69500(10)
  Cl6'' 0.65270(10)
  0.17900(10)
  0.70340(10)
  H1 0.320(5) 0.228(2) 0.937(3)
  H4 -0.193(7) 0.174(3) 1.034(4)
  H5a 0.056(6) 0.182(3) 1.193(4)
  H5b 0.076(8) 0.099(3) 1.145(5)
  H6a 0.349(6) 0.123(3) 1.098(4)
  H6b 0.317(8) 0.202(3) 1.136(5)
  H7a 0.051(6) 0.278(3) 1.027(4)
  H7b -0.031(6) 0.250(3) 0.895(4)
  H4'a 0.250(6) 0.004(3) 0.894(4)
  H4'b 0.405(6) 0.062(2) 0.933(4)
  H3'' 0.625(6) -0.137(3) 0.599(4)
  H4'' 0.868(6) -0.060(3) 0.546(4)
  H5'' 0.883(6) 0.074(3) 0.607(3)
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  C1 0.056(2)  0.0430(19) 0.072(3)  -0.0121(16) 0.006(2)  0.0027(17)
  C2 0.0473(18) 0.0369(16) 0.0409(18) 0.0042(13) 0.0092(15) 0.0074(13)
  C3 0.0521(19) 0.0376(16) 0.0431(19) 0.0004(15) 0.0057(15) 0.0038(13)
  O3 0.0697(17) 0.0519(13) 0.0610(17) -0.0184(12) 0.0012(13) 0.0033(12)
  C4 0.058(2)  0.058(2)  0.067(3)  -0.0073(18) 0.016(2)  -0.0119(19)
  C5 0.095(4)  0.062(3)  0.049(3)  -0.004(2)  0.009(2)  -0.016(2)
  C6 0.075(3)  0.065(3)  0.070(3)  -0.008(2)  -0.013(3)  -0.017(2)
  C7 0.088(3)  0.0397(19) 0.070(3)  0.0053(19) 0.010(3)  -0.010(2)
  O1' 0.0491(13) 0.0568(13) 0.0493(13) 0.0208(11) 0.0149(11) 0.0134(11)
  N2' 0.0397(13) 0.0504(15) 0.0486(17) 0.0061(12) 0.0104(13) 0.0062(13)
  C3' 0.0355(15) 0.0359(15) 0.0438(18) 0.0011(12) 0.0026(13) 0.0070(13)
  C4' 0.063(2)  0.052(2)  0.049(2)  0.0207(18) 0.0156(19) 0.0145(17)
  C1'' 0.0365(16) 0.0449(16) 0.0389(18) 0.0050(13) 0.0036(13) 0.0040(13)
  C2'' 0.0480(19) 0.0469(18) 0.054(2)  0.0031(15) 0.0044(17) -0.0016(16)
  C3'' 0.067(3)  0.056(2)  0.067(3)  0.0157(19) 0.006(2)  -0.012(2)
  C4'' 0.051(2)  0.087(3)  0.059(3)  0.013(2)  0.014(2)  -0.012(2)
  C5'' 0.039(2)  0.081(3)  0.061(3)  0.0017(19) 0.0094(19) -0.002(2)
  C6'' 0.0363(15) 0.0497(18) 0.052(2)  0.0011(13) 0.0016(15) 0.0048(15)
  Cl2'' 0.0692(6) 0.0502(5) 0.1050(9) -0.0142(5) 0.0165(6) -0.0029(5)
  Cl6'' 0.0460(5) 0.0508(5) 0.01248(11) -0.0065(4) 0.0091(6) 0.0024(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  C1 C2 . . 1.532(5) yes
  C1 C6 . . 1.534(6) yes
  C1 C7 . . 1.524(6) yes
  C2 C4' . . 1.516(5) yes
  C2 C3 . . 1.541(5) yes
  C3 C4 . . 1.494(5) yes
  C3 O3 . . 1.212(4) yes
  C4 C5 . . 1.549(6) yes
  C4 C7 . . 1.524(6) yes
  C5 C6 . . 1.540(7) yes
  O1' N2' . . 1.409(4) yes
  O1' C2 . . 1.473(4) yes
  N2' C3' . . 1.272(4) yes
  C3' C4' . . 1.494(5) yes
  C3' C1'' . . 1.471(5) yes
  C1'' C2'' . . 1.396(5) yes
  C1'' C6'' . . 1.397(4) yes
  C2'' C3'' . . 1.385(6) yes
  C2'' Cl2'' . . 1.730(4) yes
  C3'' C4'' . . 1.379(6) yes
  C4'' C5'' . . 1.375(7) yes
  C5'' C6'' . . 1.373(5) yes
  C6'' Cl6'' . . 1.741(4) yes