data_2013935
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2004
_journal_volume  60
_journal_page_first  o427
_journal_page_last  o430
_publ_section_title
;
Exo Diels-Alder adducts between ortho- and para-N-acetoxyphenyl
maleimides, and furan.
;
loop_
_publ_author_name
  "Jose G. Trujillo-Ferrara"
  "Efr\'en V. Garc\'ia-B\'aez"
  "Itzia I. Padilla-Mart\'inez"
  "Francisco J. Mart\'inez-Mart\'inez"
  'Norberto Farfan-Garc\'ia'
_chemical_formula_moiety  'C16 H13 N O5'
_chemical_formula_sum  'C16 H13 N O5'
_chemical_formula_weight  299.27
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
  x,y,z
  1/2-x,1/2+y,1/2-z
  -x,-y,-z
  1/2+x,1/2-y,1/2+z
_cell_length_a  9.7030(10)
_cell_length_b  15.8560(10)
_cell_length_c  18.8450(19)
_cell_angle_alpha  90.00
_cell_angle_beta  101.962(5)
_cell_angle_gamma  90.00
_cell_volume  2836.4(4)
_cell_formula_units_Z  8
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.402
_diffrn_ambient_temperature  293(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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
  O1 -0.0191(2) -0.16913(14) 0.11849(12) 0.0746(9) Uani . . 1.000 O
  O3 0.1657(2) -0.00908(14) 0.01384(11) 0.0744(9) Uani . . 1.000 O
  O5 0.1441(3) -0.01752(15) 0.25202(11) 0.0858(10) Uani . . 1.000 O
  O16 0.0880(2) 0.35516(12) 0.15138(10) 0.0630(8) Uani . . 1.000 O
  O17 0.0795(3) 0.37797(15) 0.03384(13) 0.0946(10) Uani . . 1.000 O
  N4 0.1473(2) 0.00695(14) 0.13263(12) 0.0512(8) Uani . . 1.000 N
  C1 0.0690(3) -0.1885(2) 0.06816(18) 0.0707(12) Uani . . 1.000 C
  C2 0.1958(3) -0.12936(17) 0.09564(15) 0.0544(10) Uani . . 1.000 C
  C3 0.1693(3) -0.03871(18) 0.07322(16) 0.0544(11) Uani . . 1.000 C
  C5 0.1623(3) -0.04275(18) 0.19440(16) 0.0575(11) Uani . . 1.000 C
  C6 0.2010(3) -0.13028(17) 0.17702(15) 0.0546(10) Uani . . 1.000 C
  C7 0.0815(3) -0.1938(2) 0.18225(17) 0.0693(12) Uani . . 1.000 C
  C8 0.1279(4) -0.2790(2) 0.1611(2) 0.0843(16) Uani . . 1.000 C
  C9 0.1210(4) -0.2759(2) 0.0918(2) 0.0837(16) Uani . . 1.000 C
  C10 0.1276(3) 0.09630(17) 0.13336(13) 0.0489(9) Uani . . 1.000 C
  C11 0.2287(3) 0.1484(2) 0.11614(18) 0.0711(13) Uani . . 1.000 C
  C12 0.2143(3) 0.23500(19) 0.12056(19) 0.0739(14) Uani . . 1.000 C
  C13 0.0997(3) 0.26800(17) 0.14145(14) 0.0526(10) Uani . . 1.000 C
  C14 -0.0035(3) 0.21669(18) 0.15609(15) 0.0583(11) Uani . . 1.000 C
  C15 0.0105(3) 0.13043(18) 0.15254(15) 0.0564(11) Uani . . 1.000 C
  C17 0.0838(3) 0.4056(2) 0.09228(18) 0.0616(11) Uani . . 1.000 C
  C18 0.0844(4) 0.49638(19) 0.11220(19) 0.0785(14) Uani . . 1.000 C
  O21 1.00593(19) 0.46221(12) 0.32806(10) 0.0573(7) Uani . . 1.000 O
  O23 0.9221(2) 0.34904(12) 0.48155(10) 0.0720(8) Uani . . 1.000 O
  O25 0.7380(2) 0.29353(12) 0.24434(10) 0.0636(7) Uani . . 1.000 O
  O36 0.9386(2) -0.04083(12) 0.41482(11) 0.0705(8) Uani . . 1.000 O
  O37 0.7207(3) -0.08364(16) 0.4113(2) 0.1404(16) Uani . . 1.000 O
  N24 0.8376(2) 0.30206(13) 0.36563(10) 0.0437(7) Uani . . 1.000 N
  C21 0.9522(3) 0.50362(17) 0.38433(15) 0.0561(10) Uani . . 1.000 C
  C22 0.8220(3) 0.44778(16) 0.38632(13) 0.0473(9) Uani . . 1.000 C
  C23 0.8664(3) 0.36358(17) 0.41917(15) 0.0495(9) Uani . . 1.000 C
  C25 0.7769(3) 0.33530(17) 0.29842(14) 0.0454(9) Uani . . 1.000 C
  C26 0.7681(3) 0.42965(15) 0.30516(13) 0.0436(8) Uani . . 1.000 C
  C27 0.8817(3) 0.47567(18) 0.27199(15) 0.0568(10) Uani . . 1.000 C
  C28 0.8562(3) 0.56844(19) 0.28022(19) 0.0681(11) Uani . . 1.000 C
  C29 0.8980(3) 0.58555(19) 0.34885(18) 0.0658(11) Uani . . 1.000 C
  C30 0.8623(3) 0.21400(16) 0.37867(13) 0.0440(9) Uani . . 1.000 C
  C31 0.9615(3) 0.17200(18) 0.34938(15) 0.0551(10) Uani . . 1.000 C
  C32 0.9820(3) 0.08666(18) 0.36162(15) 0.0579(11) Uani . . 1.000 C
  C33 0.9040(3) 0.04472(16) 0.40281(15) 0.0520(10) Uani . . 1.000 C
  C34 0.8054(3) 0.08589(18) 0.43337(15) 0.0555(10) Uani . . 1.000 C
  C35 0.7835(3) 0.17141(16) 0.41975(14) 0.0516(10) Uani . . 1.000 C
  C37 0.8424(4) -0.0994(2) 0.41970(18) 0.0723(12) Uani . . 1.000 C
  C38 0.9026(4) -0.18475(18) 0.43178(19) 0.0855(14) Uani . . 1.000 C
  H1A 0.02431 -0.18261 0.01677 0.0851 Uiso . . 1.000 H
  H2A 0.28300 -0.15098 0.08381 0.0653 Uiso . . 1.000 H
  H6A 0.29285 -0.14788 0.20535 0.0655 Uiso . . 1.000 H
  H7A 0.04743 -0.19215 0.22767 0.0836 Uiso . . 1.000 H
  H8A 0.15580 -0.32469 0.19169 0.1015 Uiso . . 1.000 H
  H9A 0.14353 -0.31876 0.06246 0.1003 Uiso . . 1.000 H
  H11A 0.30662 0.12565 0.10153 0.0854 Uiso . . 1.000 H
  H12A 0.28296 0.27051 0.10926 0.0886 Uiso . . 1.000 H
  H14A -0.08330 0.23988 0.16848 0.0701 Uiso . . 1.000 H
  H15A -0.05938 0.09535 0.16312 0.0678 Uiso . . 1.000 H
  H18A 0.10675 0.52984 0.07364 0.1176 Uiso . . 1.000 H
  H18B 0.15371 0.50588 0.15582 0.1176 Uiso . . 1.000 H
  H18C -0.00689 0.51202 0.11999 0.1176 Uiso . . 1.000 H
  H21A 1.01939 0.50921 0.43071 0.0674 Uiso . . 1.000 H
  H22A 0.75201 0.47590 0.40885 0.0567 Uiso . . 1.000 H
  H26A 0.67293 0.45148 0.28680 0.0523 Uiso . . 1.000 H
  H27A 0.88888 0.45735 0.22322 0.0682 Uiso . . 1.000 H
  H28A 0.81808 0.60609 0.24353 0.0815 Uiso . . 1.000 H
  H29A 0.89498 0.63755 0.37130 0.0790 Uiso . . 1.000 H
  H31A 1.01452 0.20101 0.32146 0.0660 Uiso . . 1.000 H
  H32A 1.04869 0.05788 0.34188 0.0696 Uiso . . 1.000 H
  H34A 0.75473 0.05699 0.46248 0.0666 Uiso . . 1.000 H
  H35A 0.71525 0.19993 0.43851 0.0620 Uiso . . 1.000 H
  H38A 0.83326 -0.22245 0.44360 0.1282 Uiso . . 1.000 H
  H38B 0.98330 -0.18344 0.47108 0.1282 Uiso . . 1.000 H
  H38C 0.93049 -0.20399 0.38855 0.1282 Uiso . . 1.000 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 0.0470(12) 0.0832(16) 0.0920(17) -0.0087(11) 0.0105(11) 0.0127(12)
  O3 0.0955(17) 0.0773(15) 0.0575(13) -0.0079(12) 0.0321(12) 0.0013(11)
  O5 0.120(2) 0.0873(17) 0.0539(13) 0.0389(14) 0.0269(13) -0.0014(11)
  O16 0.0833(15) 0.0476(12) 0.0566(12) -0.0021(10) 0.0109(10) 0.0026(10)
  O17 0.142(2) 0.0829(17) 0.0685(16) 0.0170(16) 0.0441(15) 0.0148(13)
  N4 0.0519(14) 0.0514(14) 0.0529(14) 0.0065(11) 0.0169(11) 0.0006(11)
  C1 0.073(2) 0.067(2) 0.069(2) -0.0185(18) 0.0074(16) -0.0082(17)
  C2 0.0501(16) 0.0526(18) 0.0622(17) -0.0022(13) 0.0153(13) -0.0066(14)
  C3 0.0520(18) 0.0596(19) 0.0552(18) -0.0062(14) 0.0196(14) -0.0020(15)
  C5 0.0576(19) 0.0580(19) 0.0563(18) 0.0105(15) 0.0103(14) 0.0002(15)
  C6 0.0446(16) 0.0561(18) 0.0614(18) 0.0030(13) 0.0069(13) 0.0027(14)
  C7 0.061(2) 0.075(2) 0.073(2) 0.0015(17) 0.0162(16) 0.0189(18)
  C8 0.079(3) 0.056(2) 0.117(3) -0.0077(18) 0.018(2) 0.008(2)
  C9 0.091(3) 0.055(2) 0.102(3) -0.0179(19) 0.013(2) -0.012(2)
  C10 0.0482(16) 0.0488(17) 0.0493(15) 0.0016(14) 0.0093(12) 0.0012(13)
  C11 0.0476(18) 0.062(2) 0.109(3) 0.0093(16) 0.0287(17) 0.0091(18)
  C12 0.058(2) 0.054(2) 0.114(3) -0.0072(16) 0.0279(19) 0.0094(18)
  C13 0.0590(19) 0.0473(18) 0.0516(16) 0.0071(14) 0.0119(14) 0.0018(13)
  C14 0.0546(18) 0.057(2) 0.0681(19) 0.0074(15) 0.0236(15) -0.0011(15)
  C15 0.0450(16) 0.0531(19) 0.075(2) -0.0020(14) 0.0211(14) 0.0009(15)
  C17 0.0600(19) 0.061(2) 0.064(2) 0.0012(15) 0.0131(15) 0.0101(17)
  C18 0.077(2) 0.057(2) 0.098(3) -0.0080(18) 0.0098(19) 0.0123(19)
  O21 0.0437(11) 0.0618(12) 0.0677(12) 0.0013(9) 0.0143(9) 0.0004(10)
  O23 0.1047(17) 0.0612(13) 0.0417(11) 0.0055(12) -0.0041(11) -0.0017(10)
  O25 0.0769(14) 0.0589(12) 0.0485(11) -0.0022(11) -0.0018(9) -0.0094(10)
  O36 0.0711(15) 0.0489(13) 0.0904(16) 0.0135(11) 0.0143(12) 0.0057(11)
  O37 0.075(2) 0.0623(17) 0.281(4) -0.0009(16) 0.030(2) -0.016(2)
  N24 0.0494(13) 0.0378(12) 0.0432(12) 0.0024(10) 0.0082(10) -0.0027(10)
  C21 0.0553(18) 0.0496(17) 0.0567(17) -0.0025(14) -0.0041(13) -0.0063(14)
  C22 0.0490(16) 0.0461(16) 0.0479(15) 0.0050(13) 0.0129(12) -0.0067(12)
  C23 0.0517(16) 0.0514(17) 0.0456(16) -0.0035(13) 0.0104(12) -0.0036(13)
  C25 0.0406(15) 0.0500(16) 0.0456(16) 0.0023(12) 0.0088(12) -0.0012(13)
  C26 0.0367(14) 0.0442(15) 0.0474(14) 0.0017(11) 0.0031(11) 0.0023(12)
  C27 0.0667(19) 0.0550(18) 0.0496(16) -0.0027(15) 0.0142(14) 0.0045(14)
  C28 0.064(2) 0.0529(19) 0.082(2) -0.0058(15) 0.0027(17) 0.0175(17)
  C29 0.062(2) 0.0446(18) 0.088(2) -0.0008(15) 0.0092(17) -0.0043(16)
  C30 0.0441(15) 0.0450(16) 0.0417(14) 0.0014(12) 0.0060(12) -0.0030(12)
  C31 0.0520(17) 0.057(2) 0.0591(17) 0.0019(14) 0.0182(14) -0.0001(14)
  C32 0.0536(18) 0.058(2) 0.0666(18) 0.0133(15) 0.0227(14) -0.0038(15)
  C33 0.0560(18) 0.0395(16) 0.0597(17) 0.0099(13) 0.0101(14) 0.0004(13)
  C34 0.0562(18) 0.0526(18) 0.0606(16) 0.0020(14) 0.0188(14) 0.0018(14)
  C35 0.0549(17) 0.0450(17) 0.0580(17) 0.0071(14) 0.0188(13) -0.0019(13)
  C37 0.066(2) 0.057(2) 0.088(2) 0.0057(19) 0.0024(18) -0.0031(18)
  C38 0.101(3) 0.0442(19) 0.093(2) 0.0092(18) -0.022(2) -0.0003(17)
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
  O1 C1 . . 1.436(4) yes
  O1 C7 . . 1.436(4) yes
  O3 C3 . . 1.207(4) yes
  O5 C5 . . 1.204(4) yes
  O16 C13 . . 1.402(3) yes
  O16 C17 . . 1.365(4) yes
  O17 C17 . . 1.178(4) yes
  O21 C21 . . 1.434(3) yes
  O21 C27 . . 1.445(3) yes
  O23 C23 . . 1.210(3) yes
  O25 C25 . . 1.208(3) yes
  O36 C33 . . 1.404(3) yes
  O36 C37 . . 1.333(4) yes
  O37 C37 . . 1.185(5) yes
  N4 C5 . . 1.388(4) yes
  N4 C10 . . 1.430(3) yes
  N4 C3 . . 1.386(4) yes
  N24 C23 . . 1.390(3) yes
  N24 C25 . . 1.386(3) yes
  N24 C30 . . 1.429(3) yes
  C1 C2 . . 1.548(4) no
  C1 C9 . . 1.510(5) no
  C2 C3 . . 1.505(4) no
  C2 C6 . . 1.524(4) no
  C5 C6 . . 1.492(4) no
  C6 C7 . . 1.554(4) no
  C7 C8 . . 1.504(5) no
  C8 C9 . . 1.295(5) no
  C10 C15 . . 1.373(4) no
  C10 C11 . . 1.372(4) no
  C11 C12 . . 1.384(4) no
  C12 C13 . . 1.359(4) no
  C13 C14 . . 1.362(4) no
  C14 C15 . . 1.377(4) no
  C17 C18 . . 1.487(4) no
  C1 H1A . . 0.9801 no
  C2 H2A . . 0.9805 no
  C6 H6A . . 0.9798 no
  C7 H7A . . 0.9797 no
  C8 H8A . . 0.9305 no
  C9 H9A . . 0.9303 no
  C11 H11A . . 0.9294 no
  C12 H12A . . 0.9301 no
  C14 H14A . . 0.9296 no
  C15 H15A . . 0.9300 no
  C18 H18A . . 0.9601 no
  C18 H18B . . 0.9600 no
  C18 H18C . . 0.9600 no
  C21 C22 . . 1.550(4) no
  C21 C29 . . 1.505(4) no
  C22 C23 . . 1.497(4) no
  C22 C26 . . 1.537(3) no
  C25 C26 . . 1.505(4) no
  C26 C27 . . 1.557(4) no
  C27 C28 . . 1.505(4) no
  C28 C29 . . 1.301(5) no
  C30 C31 . . 1.377(4) no
  C30 C35 . . 1.373(4) no
  C31 C32 . . 1.380(4) no
  C32 C33 . . 1.364(4) no
  C33 C34 . . 1.379(4) no
  C34 C35 . . 1.388(4) no
  C37 C38 . . 1.473(4) no
  C21 H21A . . 0.9801 no
  C22 H22A . . 0.9797 no
  C26 H26A . . 0.9797 no
  C27 H27A . . 0.9800 no
  C28 H28A . . 0.9302 no
  C29 H29A . . 0.9299 no
  C31 H31A . . 0.9302 no
  C32 H32A . . 0.9301 no
  C34 H34A . . 0.9298 no
  C35 H35A . . 0.9301 no
  C38 H38A . . 0.9601 no
  C38 H38B . . 0.9600 no
  C38 H38C . . 0.9599 no