#------------------------------------------------------------------------------
#$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $
#$Revision: 14 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2011774.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_2011774
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2001
_journal_volume  57
_journal_page_first  208
_journal_page_last  210
_publ_section_title
;
Dimethyl (1R,8R)-1,11,11-trimethyl-2,3-diazatricyclo[6.2.1.0^2,6^]undec-3,5-
diene-4,5-dicarboxylate. A chiral molecule with an approximate centrosymmetric
crystal structure
;
loop_
_publ_author_name
  'Bats, Jan W.'
  'Grundl, Marc A.'
  'Hashmi, A. Stephen K.'
_chemical_formula_moiety  'C16 H22 N2 O4'
_chemical_formula_sum  'C16 H22 N2 O4'
_chemical_formula_weight  306.36
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z'
_cell_length_a  7.3772(14)
_cell_length_b  20.063(3)
_cell_length_c  10.4576(12)
_cell_angle_alpha  90.00
_cell_angle_beta  90.513(12)
_cell_angle_gamma  90.00
_cell_volume  1547.7(4)
_cell_formula_units_Z  4
_cell_measurement_temperature  143(2)
_exptl_crystal_density_diffrn  1.315
_diffrn_ambient_temperature  143(2)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
  O1  .88181(18)  .33711(8)  .10555(12)  .0296(3) Uani d . 1 . . O
  O2  .6803(3)  .29414(15)  .23891(17)  .0704(8) Uani d . 1 . . O
  O3  .81218(17)  .52951(6)  .39547(12)  .0233(2) Uani d . 1 . . O
  O4  .71229(18)  .46974(8)  .22663(13)  .0277(3) Uani d . 1 . . O
  O5  .11490(17)  .66123(8)  .39238(12)  .0281(3) Uani d . 1 . . O
  O6  .3064(2)  .70926(9)  .25519(13)  .0362(4) Uani d . 1 . . O
  O7  .17807(17)  .47207(6)  .09718(12)  .0221(2) Uani d . 1 . . O
  O8  .28172(17)  .53138(7)  .26597(12)  .0253(3) Uani d . 1 . . O
  N1 1.11683(19)  .36006(7)  .47739(13)  .0178(3) Uani d . 1 . . N
  N2 1.0437(2)  .31789(7)  .38873(14)  .0195(3) Uani d . 1 . . N
  N3  -.13818(18)  .64008(7)  .02556(13)  .0176(3) Uani d . 1 . . N
  N4  -.06488(19)  .68205(7)  .11495(14)  .0196(3) Uani d . 1 . . N
  C1  .9274(2)  .35580(9)  .32344(16)  .0189(3) Uani d . 1 . . C
  C2  .9225(2)  .42190(8)  .37032(15)  .0181(3) Uani d . 1 . . C
  C3 1.0463(2)  .42206(8)  .47179(15)  .0175(3) Uani d . 1 . . C
  C4 1.1072(2)  .47450(8)  .56464(16)  .0212(3) Uani d . 1 . . C
  H4A 1.0007  .4990  .5973  .025 Uiso calc R 1 . . H
  H4B 1.1872  .5068  .5210  .025 Uiso calc R 1 . . H
  C5 1.2099(2)  .44188(8)  .67630(15)  .0202(3) Uani d . 1 . . C
  H5 1.2662  .4766  .7326  .024 Uiso calc R 1 . . H
  C6 1.0818(3)  .39642(9)  .75462(16)  .0251(3) Uani d . 1 . . C
  H6A 1.1167  .3969  .8463  .030 Uiso calc R 1 . . H
  H6B  .9547  .4118  .7462  .030 Uiso calc R 1 . . H
  C7 1.1030(2)  .32536(9)  .69831(17)  .0234(3) Uani d . 1 . . C
  H7A 1.1560  .2946  .7625  .028 Uiso calc R 1 . . H
  H7B  .9843  .3075  .6695  .028 Uiso calc R 1 . . H
  C8 1.2319(2)  .33439(8)  .58401(15)  .0188(3) Uani d . 1 . . C
  C9 1.3258(3)  .27105(9)  .5420(2)  .0284(4) Uani d . 1 . . C
  H9A 1.4021  .2542  .6120  .043 Uiso calc R 1 . . H
  H9B 1.4013  .2805  .4675  .043 Uiso calc R 1 . . H
  H9C 1.2346  .2375  .5192  .043 Uiso calc R 1 . . H
  C10 1.3557(2)  .39303(8)  .62697(16)  .0204(3) Uani d . 1 . . C
  C11 1.4797(3)  .37109(10)  .73899(19)  .0280(4) Uani d . 1 . . C
  H11A 1.5644  .3369  .7092  .042 Uiso calc R 1 . . H
  H11B 1.4055  .3528  .8079  .042 Uiso calc R 1 . . H
  H11C 1.5480  .4096  .7710  .042 Uiso calc R 1 . . H
  C12 1.4749(3)  .42088(11)  .52069(19)  .0297(4) Uani d . 1 . . C
  H12A 1.3990  .4328  .4468  .045 Uiso calc R 1 . . H
  H12B 1.5636  .3871  .4954  .045 Uiso calc R 1 . . H
  H12C 1.5387  .4606  .5518  .045 Uiso calc R 1 . . H
  C13  .8149(2)  .32522(10)  .21954(17)  .0242(3) Uani d . 1 . . C
  C14  .7784(3)  .31090(14)  -.00154(19)  .0360(5) Uani d . 1 . . C
  H14A  .7670  .2625  .0072  .054 Uiso calc R 1 . . H
  H14B  .8407  .3214  -.0814  .054 Uiso calc R 1 . . H
  H14C  .6575  .3311  -.0028  .054 Uiso calc R 1 . . H
  C15  .8055(2)  .47500(9)  .32170(16)  .0201(3) Uani d . 1 . . C
  C16  .6950(2)  .58352(9)  .35556(19)  .0256(3) Uani d . 1 . . C
  H16A  .7088  .6210  .4150  .038 Uiso calc R 1 . . H
  H16B  .5688  .5683  .3553  .038 Uiso calc R 1 . . H
  H16C  .7281  .5979  .2693  .038 Uiso calc R 1 . . H
  C17  .0588(2)  .64506(8)  .17458(15)  .0177(3) Uani d . 1 . . C
  C18  .0666(2)  .57964(8)  .12528(16)  .0172(3) Uani d . 1 . . C
  C19  -.0649(2)  .57862(8)  .02850(15)  .0165(3) Uani d . 1 . . C
  C20  -.1272(2)  .52661(8)  -.06404(16)  .0200(3) Uani d . 1 . . C
  H20A  -.1537  .4848  -.0177  .024 Uiso calc R 1 . . H
  H20B  -.0301  .5174  -.1264  .024 Uiso calc R 1 . . H
  C21  -.2979(2)  .55042(8)  -.13485(15)  .0205(3) Uani d . 1 . . C
  H21  -.3280  .5197  -.2073  .025 Uiso calc R 1 . . H
  C22  -.4595(2)  .55542(10)  -.04149(18)  .0260(3) Uani d . 1 . . C
  H22A  -.5742  .5430  -.0853  .031 Uiso calc R 1 . . H
  H22B  -.4409  .5254  .0326  .031 Uiso calc R 1 . . H
  C23  -.4658(2)  .62900(10)  .00278(16)  .0246(3) Uani d . 1 . . C
  H23A  -.5772  .6512  -.0291  .030 Uiso calc R 1 . . H
  H23B  -.4622  .6320  .0973  .030 Uiso calc R 1 . . H
  C24  -.2961(2)  .66110(8)  -.05540(15)  .0184(3) Uani d . 1 . . C
  C25  -.3015(3)  .73665(9)  -.06424(19)  .0275(4) Uani d . 1 . . C
  H25A  -.4003  .7502  -.1219  .041 Uiso calc R 1 . . H
  H25B  -.1860  .7530  -.0975  .041 Uiso calc R 1 . . H
  H25C  -.3218  .7555  .0209  .041 Uiso calc R 1 . . H
  C26  -.2758(2)  .62291(8)  -.18384(15)  .0190(3) Uani d . 1 . . C
  C27  -.4328(3)  .63938(10)  -.27623(17)  .0286(4) Uani d . 1 . . C
  H27A  -.4278  .6867  -.2994  .043 Uiso calc R 1 . . H
  H27B  -.5485  .6299  -.2346  .043 Uiso calc R 1 . . H
  H27C  -.4223  .6121  -.3535  .043 Uiso calc R 1 . . H
  C28  -.0981(3)  .63737(10)  -.25246(17)  .0281(4) Uani d . 1 . . C
  H28A  -.0985  .6835  -.2832  .042 Uiso calc R 1 . . H
  H28B  -.0856  .6070  -.3252  .042 Uiso calc R 1 . . H
  H28C  .0038  .6309  -.1930  .042 Uiso calc R 1 . . H
  C29  .1754(2)  .67532(8)  .27676(16)  .0194(3) Uani d . 1 . . C
  C30  .2285(3)  .68466(13)  .49677(18)  .0349(5) Uani d . 1 . . C
  H30A  .3537  .6702  .4830  .052 Uiso calc R 1 . . H
  H30B  .1847  .6662  .5775  .052 Uiso calc R 1 . . H
  H30C  .2239  .7334  .5004  .052 Uiso calc R 1 . . H
  C31  .1866(2)  .52672(8)  .17170(15)  .0176(3) Uani d . 1 . . C
  C32  .2928(2)  .41720(9)  .13646(19)  .0247(3) Uani d . 1 . . C
  H32A  .4188  .4324  .1426  .037 Uiso calc R 1 . . H
  H32B  .2836  .3812  .0734  .037 Uiso calc R 1 . . H
  H32C  .2536  .4008  .2200  .037 Uiso calc R 1 . . H
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
  O1  .0250(6)  .0453(8)  .0186(6)  -.0110(6)  .0002(5)  -.0071(6)
  O2  .0664(13)  .117(2)  .0275(8)  -.0665(14)  -.0082(8)  .0059(10)
  O3  .0253(6)  .0182(5)  .0264(6)  .0021(5)  -.0065(5)  .0039(5)
  O4  .0262(6)  .0348(7)  .0220(6)  .0056(5)  -.0071(5)  .0014(5)
  O5  .0216(6)  .0437(8)  .0190(6)  -.0081(6)  -.0023(4)  -.0035(6)
  O6  .0355(7)  .0477(9)  .0253(7)  -.0227(7)  -.0046(5)  -.0003(6)
  O7  .0235(6)  .0152(5)  .0274(6)  .0031(4)  -.0055(4)  -.0003(5)
  O8  .0230(6)  .0255(6)  .0273(6)  .0044(5)  -.0073(5)  -.0018(5)
  N1  .0210(6)  .0149(6)  .0174(6)  .0005(5)  -.0045(5)  -.0020(5)
  N2  .0224(6)  .0174(6)  .0188(6)  -.0011(5)  -.0038(5)  -.0027(5)
  N3  .0198(6)  .0138(6)  .0191(6)  .0005(5)  -.0046(5)  -.0020(5)
  N4  .0210(6)  .0170(6)  .0205(6)  .0002(5)  -.0051(5)  -.0047(5)
  C1  .0187(7)  .0207(7)  .0174(7)  -.0031(6)  -.0011(5)  .0002(6)
  C2  .0173(7)  .0194(7)  .0177(7)  -.0002(6)  -.0013(5)  .0026(6)
  C3  .0192(7)  .0161(6)  .0172(7)  .0004(5)  -.0003(5)  .0014(5)
  C4  .0275(8)  .0151(7)  .0210(7)  .0014(6)  -.0062(6)  -.0005(6)
  C5  .0266(8)  .0150(6)  .0189(7)  -.0011(6)  -.0054(6)  -.0017(5)
  C6  .0315(9)  .0265(8)  .0175(7)  -.0003(7)  .0024(6)  -.0017(6)
  C7  .0296(8)  .0192(7)  .0215(7)  -.0037(6)  -.0004(6)  .0030(6)
  C8  .0231(7)  .0156(6)  .0176(7)  .0018(5)  -.0059(5)  .0004(5)
  C9  .0324(9)  .0199(8)  .0326(9)  .0098(7)  -.0105(7)  -.0055(7)
  C10  .0213(7)  .0190(7)  .0209(7)  -.0008(6)  -.0055(6)  .0002(6)
  C11  .0293(9)  .0247(8)  .0300(9)  -.0003(7)  -.0139(7)  .0005(7)
  C12  .0229(8)  .0342(10)  .0321(9)  -.0046(7)  .0008(7)  .0042(8)
  C13  .0251(8)  .0279(8)  .0195(7)  -.0065(7)  -.0064(6)  .0014(6)
  C14  .0336(10)  .0541(13)  .0203(8)  -.0105(9)  -.0038(7)  -.0083(9)
  C15  .0169(7)  .0223(7)  .0211(7)  -.0007(6)  .0007(5)  .0052(6)
  C16  .0252(8)  .0194(7)  .0320(9)  .0048(6)  -.0024(7)  .0057(7)
  C17  .0179(7)  .0167(7)  .0183(7)  -.0016(5)  -.0019(5)  -.0026(5)
  C18  .0170(6)  .0142(6)  .0204(7)  .0002(5)  -.0014(5)  -.0006(5)
  C19  .0176(6)  .0140(6)  .0178(7)  -.0001(5)  -.0007(5)  -.0008(5)
  C20  .0259(8)  .0141(6)  .0199(7)  -.0004(6)  -.0041(6)  -.0038(6)
  C21  .0263(8)  .0173(6)  .0178(7)  -.0035(6)  -.0056(6)  .0000(5)
  C22  .0215(7)  .0291(8)  .0273(8)  -.0067(6)  -.0028(6)  .0080(7)
  C23  .0196(7)  .0331(9)  .0213(7)  .0020(6)  .0007(6)  .0013(7)
  C24  .0187(7)  .0186(7)  .0178(7)  .0022(5)  -.0046(5)  -.0004(5)
  C25  .0315(9)  .0176(7)  .0331(9)  .0069(7)  -.0098(7)  -.0020(7)
  C26  .0231(7)  .0177(6)  .0162(6)  -.0010(6)  -.0020(5)  .0018(5)
  C27  .0362(9)  .0281(8)  .0214(8)  .0001(7)  -.0101(7)  .0040(7)
  C28  .0340(9)  .0250(8)  .0255(8)  -.0005(7)  .0084(7)  .0028(7)
  C29  .0191(7)  .0180(7)  .0209(7)  .0003(5)  -.0027(5)  -.0027(6)
  C30  .0272(9)  .0578(14)  .0195(8)  -.0084(9)  -.0044(7)  -.0071(8)
  C31  .0157(6)  .0164(6)  .0207(7)  -.0009(5)  .0000(5)  .0015(6)
  C32  .0230(8)  .0164(7)  .0347(9)  .0044(6)  -.0014(6)  .0033(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  O1 C13 . 1.316(2) ?
  O1 C14 . 1.448(2) ?
  O2 C13 . 1.191(3) ?
  O3 C15 . 1.339(2) ?
  O3 C16 . 1.445(2) ?
  O4 C15 . 1.209(2) ?
  O5 C29 . 1.323(2) ?
  O5 C30 . 1.449(2) ?
  O6 C29 . 1.205(2) ?
  O7 C31 . 1.346(2) ?
  O7 C32 . 1.446(2) ?
  O8 C31 . 1.209(2) ?
  N1 C3 . 1.349(2) ?
  N1 N2 . 1.3631(19) ?
  N1 C8 . 1.487(2) ?
  N2 C1 . 1.330(2) ?
  N3 C19 . 1.347(2) ?
  N3 N4 . 1.3660(18) ?
  N3 C24 . 1.495(2) ?
  N4 C17 . 1.327(2) ?
  C1 C2 . 1.414(2) ?
  C1 C13 . 1.493(2) ?
  C2 C3 . 1.394(2) ?
  C2 C15 . 1.460(2) ?
  C3 C4 . 1.498(2) ?
  C4 C5 . 1.533(2) ?
  C5 C10 . 1.547(2) ?
  C5 C6 . 1.552(2) ?
  C6 C7 . 1.551(3) ?
  C7 C8 . 1.545(2) ?
  C8 C9 . 1.514(2) ?
  C8 C10 . 1.553(2) ?
  C10 C12 . 1.529(3) ?
  C10 C11 . 1.544(2) ?
  C17 C18 . 1.411(2) ?
  C17 C29 . 1.495(2) ?
  C18 C19 . 1.396(2) ?
  C18 C31 . 1.462(2) ?
  C19 C20 . 1.493(2) ?
  C20 C21 . 1.532(2) ?
  C21 C26 . 1.551(2) ?
  C21 C22 . 1.551(3) ?
  C22 C23 . 1.548(3) ?
  C23 C24 . 1.538(2) ?
  C24 C25 . 1.519(2) ?
  C24 C26 . 1.555(2) ?
  C26 C28 . 1.528(2) ?
  C26 C27 . 1.538(2) ?