data_2014318
_journal_name_full 'Acta Crystallographica, Section C'
_journal_year 2006
_journal_volume 62
_journal_page_first o125
_journal_page_last o128
_publ_section_title
;
Two isomeric butadiene-N-acetoxyphenyl maleimide Diels--Alder adducts:
supramolecular structure directed by C---H...X (X = O and \p)
hydrogen bonds and perpendicular dipole carbonyl--carbonyl interactions
;
loop_
_publ_author_name
"Jose G. Trujillo-Ferrara"
'Rosa Luisa Santill\'an-Baca'
'Norberto Farf\'an-Garc\'ia'
"Itzia I. Padilla-Mart\'inez"
"Efr\'en V. Garc\'ia-B\'aez"
_chemical_formula_moiety 'C16 H15 N O4'
_chemical_formula_sum 'C16 H15 N O4'
_chemical_formula_iupac 'C16 H15 N O4'
_chemical_formula_weight 285.17
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M 'P 21/c'
_symmetry_space_group_name_Hall '-P 2ybc'
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z
_cell_length_a 16.1630(10)
_cell_length_b 6.5780(10)
_cell_length_c 13.5830(10)
_cell_angle_alpha 90
_cell_angle_beta 93.73(2)
_cell_angle_gamma 90
_cell_volume 1441.1(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 293(2)
_exptl_crystal_density_diffrn 1.314
_diffrn_ambient_temperature 100(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
O O1 0.24578(12) 1.0321(3) 0.36249(11) 0.0745(6) Uani . . 1.000
O O3 0.32688(9) 0.5160(2) 0.16956(10) 0.0545(5) Uani . . 1.000
O O14 0.09535(9) 1.1923(2) -0.05900(10) 0.0594(5) Uani . . 1.000
O O15 0.13805(12) 1.0021(3) -0.18105(12) 0.0783(7) Uani . . 1.000
N N2 0.27355(9) 0.7906(2) 0.24784(10) 0.0373(4) Uani . . 1.000
C C1 0.27588(12) 0.8706(3) 0.34267(12) 0.0440(5) Uani . . 1.000
C C3 0.31379(11) 0.6035(3) 0.24479(13) 0.0379(5) Uani . . 1.000
C C3A 0.33652(11) 0.5372(3) 0.34991(13) 0.0415(5) Uani . . 1.000
C C4 0.42418(13) 0.4502(4) 0.36141(17) 0.0595(8) Uani . . 1.000
C C5 0.48488(14) 0.6157(5) 0.35188(17) 0.0714(9) Uani . . 1.000
C C6 0.47444(15) 0.7922(5) 0.39272(17) 0.0712(9) Uani . . 1.000
C C7 0.40345(15) 0.8269(4) 0.45524(16) 0.0664(8) Uani . . 1.000
C C7A 0.32243(11) 0.7265(3) 0.41193(12) 0.0446(6) Uani . . 1.000
C C8 0.23068(10) 0.8862(3) 0.16447(12) 0.0369(5) Uani . . 1.000
C C9 0.16453(11) 0.7883(3) 0.11522(13) 0.0449(6) Uani . . 1.000
C C10 0.12072(12) 0.8847(3) 0.03805(14) 0.0496(6) Uani . . 1.000
C C11 0.14337(11) 1.0790(3) 0.01249(13) 0.0451(6) Uani . . 1.000
C C12 0.21008(12) 1.1761(3) 0.05959(14) 0.0470(6) Uani . . 1.000
C C13 0.25389(12) 1.0786(3) 0.13636(13) 0.0431(5) Uani . . 1.000
C C15 0.10087(12) 1.1449(4) -0.15435(15) 0.0535(7) Uani . . 1.000
C C16 0.05530(15) 1.2987(4) -0.21816(18) 0.0721(9) Uani . . 1.000
H H3A 0.29744 0.43167 0.36789 0.0499 Uiso . . 1.000
H H4B 0.43314 0.38597 0.42549 0.0715 Uiso . . 1.000
H H4C 0.43126 0.34819 0.31110 0.0715 Uiso . . 1.000
H H5 0.53125 0.59349 0.31620 0.0856 Uiso . . 1.000
H H6 0.51153 0.89718 0.38276 0.0852 Uiso . . 1.000
H H7A 0.28764 0.69095 0.46583 0.0535 Uiso . . 1.000
H H7B 0.39453 0.97201 0.46174 0.0796 Uiso . . 1.000
H H7C 0.41714 0.77245 0.52064 0.0796 Uiso . . 1.000
H H9 0.14962 0.65812 0.13401 0.0539 Uiso . . 1.000
H H10 0.07660 0.81969 0.00380 0.0595 Uiso . . 1.000
H H12 0.22543 1.30548 0.04003 0.0565 Uiso . . 1.000
H H13 0.29904 1.14239 0.16916 0.0518 Uiso . . 1.000
H H16A 0.05464 1.25628 -0.28583 0.1082 Uiso . . 1.000
H H16B 0.08257 1.42792 -0.21080 0.1082 Uiso . . 1.000
H H16C -0.00058 1.31050 -0.19883 0.1082 Uiso . . 1.000
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 0.1075(14) 0.0669(10) 0.0478(8) 0.0385(10) -0.0045(8) -0.0153(7)
O3 0.0727(10) 0.0433(7) 0.0467(8) 0.0079(7) -0.0017(7) -0.0113(6)
O14 0.0565(9) 0.0715(10) 0.0496(8) 0.0167(8) -0.0017(6) 0.0110(7)
O15 0.0840(12) 0.0933(13) 0.0561(10) 0.0261(10) -0.0074(8) -0.0125(9)
N2 0.0447(8) 0.0345(7) 0.0323(7) 0.0015(6) -0.0007(5) 0.0001(5)
C1 0.0523(10) 0.0451(10) 0.0346(8) 0.0066(8) 0.0019(7) -0.0043(7)
C3 0.0430(9) 0.0306(8) 0.0397(8) -0.0045(7) 0.0003(7) -0.0013(7)
C3A 0.0439(10) 0.0374(9) 0.0430(9) -0.0027(8) 0.0003(7) 0.0064(7)
C4 0.0587(13) 0.0656(14) 0.0536(12) 0.0191(11) -0.0019(9) 0.0069(10)
C5 0.0415(11) 0.120(2) 0.0523(12) -0.0006(14) 0.0002(9) 0.0062(14)
C6 0.0579(14) 0.097(2) 0.0564(13) -0.0329(14) -0.0130(10) 0.0133(13)
C7 0.0812(16) 0.0655(14) 0.0490(11) 0.0009(12) -0.0214(10) -0.0095(10)
C7A 0.0495(10) 0.0515(11) 0.0329(8) 0.0038(8) 0.0038(7) 0.0035(8)
C8 0.0406(9) 0.0367(8) 0.0333(7) 0.0029(7) 0.0017(6) 0.0008(7)
C9 0.0460(10) 0.0430(10) 0.0456(9) -0.0090(8) 0.0012(7) 0.0062(8)
C10 0.0413(9) 0.0596(12) 0.0467(10) -0.0087(9) -0.0059(8) 0.0054(9)
C11 0.0427(10) 0.0531(11) 0.0393(9) 0.0084(8) 0.0023(7) 0.0064(8)
C12 0.0548(11) 0.0402(10) 0.0461(10) -0.0006(9) 0.0031(8) 0.0052(8)
C13 0.0487(10) 0.0372(9) 0.0426(9) -0.0034(8) -0.0033(8) 0.0008(7)
C15 0.0419(10) 0.0687(14) 0.0492(10) -0.0001(10) -0.0024(8) 0.0066(10)
C16 0.0602(14) 0.0900(18) 0.0643(14) 0.0033(13) -0.0100(10) 0.0289(13)
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 . . 1.206(3) no
O3 C3 . . 1.204(2) no
O14 C11 . . 1.415(2) yes
O14 C15 . . 1.341(2) yes
O15 C15 . . 1.185(3) no
N2 C1 . . 1.390(2) yes
N2 C3 . . 1.394(2) yes
N2 C8 . . 1.434(2) yes
C1 C7A . . 1.503(3) no
C3 C3A . . 1.515(3) no
C3A C4 . . 1.527(3) no
C3A C7A . . 1.529(3) no
C4 C5 . . 1.477(4) no
C5 C6 . . 1.302(4) no
C6 C7 . . 1.489(3) no
C7 C7A . . 1.548(3) no
C8 C9 . . 1.383(3) no
C8 C13 . . 1.381(3) no
C9 C10 . . 1.381(3) no
C10 C11 . . 1.380(3) no
C11 C12 . . 1.375(3) no
C12 C13 . . 1.380(3) no
C15 C16 . . 1.495(3) no
C3A H3A . . 0.98 no
C4 H4B . . 0.97 no
C4 H4C . . 0.97 no
C5 H5 . . 0.93 no
C6 H6 . . 0.93 no
C7 H7B . . 0.97 no
C7 H7C . . 0.97 no
C7A H7A . . 0.98 no
C9 H9 . . 0.93 no
C10 H10 . . 0.93 no
C12 H12 . . 0.93 no
C13 H13 . . 0.93 no
C16 H16A . . 0.96 no
C16 H16B . . 0.96 no
C16 H16C . . 0.96 no