data_2011189
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2000
_journal_volume  56
_journal_page_first  971
_journal_page_last  975
_publ_section_title
;
A combinatorial chemistry approach to new materials for nonlinear
optics. I. Structures of five Schiff bases
;
loop_
_publ_author_name
  'Vladimir N. Nesterov'
  'Tatiana V. Timofeeva'
  'Oleg Ya. Borbulevych'
  'Mikhail Yu. Antipin'
  'Ronald D. Clark'
_chemical_formula_sum  'C16 H14 N2 O3'
_chemical_formula_weight  282.29
_chemical_melting_point  141.0(10)
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'P 21/n'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x-1/2, -y-1/2, z-1/2'
_cell_length_a  15.7883(8)
_cell_length_b  3.9239(2)
_cell_length_c  22.6063(11)
_cell_angle_alpha  90.00
_cell_angle_beta  105.7670(10)
_cell_angle_gamma  90.00
_cell_volume  1347.80(12)
_cell_formula_units_Z  4
_cell_measurement_temperature  100(2)
_exptl_crystal_density_diffrn  1.391
_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
_atom_site_disorder_group
_atom_site_type_symbol
  N1  .71571(7)  .8307(3)  .47857(5)  .0230(2) Uani d . 1 . N
  N2  .58671(8) 1.3183(3)  .63606(6)  .0301(3) Uani d . 1 . N
  O1  .52247(7) 1.4097(3)  .59496(5)  .0394(3) Uani d . 1 . O
  O2  .59540(8) 1.3733(3)  .69088(5)  .0437(3) Uani d . 1 . O
  O3  .54119(6)  .8769(2)  .06917(4)  .0257(2) Uani d . 1 . O
  C1  .71743(8)  .9150(3)  .53949(6)  .0210(3) Uani d . 1 . C
  C2  .64822(9) 1.0745(3)  .55690(6)  .0226(3) Uani d . 1 . C
  H2  .5942(11) 1.138(4)  .5271(7)  .028(4) Uiso d . 1 . H
  C3  .65833(9) 1.1368(3)  .61860(6)  .0236(3) Uani d . 1 . C
  C4  .73237(9) 1.0458(3)  .66461(6)  .0260(3) Uani d . 1 . C
  H4  .7366(11) 1.097(4)  .7085(7)  .038(4) Uiso d . 1 . H
  C5  .80030(9)  .8853(3)  .64703(6)  .0255(3) Uani d . 1 . C
  H5  .8529(12)  .815(4)  .6774(7)  .038(4) Uiso d . 1 . H
  C6  .79286(9)  .8229(3)  .58547(6)  .0234(3) Uani d . 1 . C
  H6  .8377(11)  .714(4)  .5731(7)  .032(4) Uiso d . 1 . H
  C7  .66406(8)  .9937(3)  .43370(6)  .0230(3) Uani d . 1 . C
  H7  .6275(10) 1.180(4)  .4396(6)  .020(3) Uiso d . 1 . H
  C8  .65983(9)  .9134(3)  .37074(6)  .0229(3) Uani d . 1 . C
  H8  .6997(11)  .733(4)  .3628(7)  .034(4) Uiso d . 1 . H
  C9  .60137(8) 1.0693(3)  .32388(6)  .0219(3) Uani d . 1 . C
  H9  .5599(10) 1.227(4)  .3332(6)  .024(4) Uiso d . 1 . H
  C10  .58973(8) 1.0143(3)  .25832(5)  .0203(3) Uani d . 1 . C
  C11  .51440(8) 1.1443(3)  .21595(6)  .0216(3) Uani d . 1 . C
  H11  .4748(11) 1.273(4)  .2310(7)  .032(4) Uiso d . 1 . H
  C12  .50053(8) 1.0972(3)  .15374(6)  .0227(3) Uani d . 1 . C
  H12  .4502(11) 1.190(4)  .1240(7)  .032(4) Uiso d . 1 . H
  C13  .56219(8)  .9180(3)  .13143(6)  .0211(3) Uani d . 1 . C
  C14  .63867(8)  .7953(3)  .17250(6)  .0218(3) Uani d . 1 . C
  H14  .6816(10)  .670(4)  .1561(6)  .024(4) Uiso d . 1 . H
  C15  .65141(8)  .8408(3)  .23524(6)  .0213(3) Uani d . 1 . C
  H15  .7062(10)  .747(4)  .2635(6)  .023(4) Uiso d . 1 . H
  C16  .60435(10)  .7113(4)  .04374(7)  .0268(3) Uani d . 1 . C
  H16C  .6175(10)  .487(4)  .0605(6)  .027(4) Uiso d . 1 . H
  H16B  .6583(11)  .851(4)  .0515(7)  .032(4) Uiso d . 1 . H
  H16A  .5766(10)  .699(4)  -.0017(7)  .031(4) Uiso d . 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
  N1  .0232(5)  .0245(5)  .0222(5)  .0005(4)  .0075(4)  -.0016(4)
  N2  .0297(6)  .0289(6)  .0371(7)  .0004(5)  .0183(5)  -.0004(5)
  O1  .0295(6)  .0480(7)  .0441(6)  .0102(5)  .0158(5)  .0049(5)
  O2  .0468(7)  .0547(7)  .0364(6)  .0049(6)  .0229(5)  -.0075(5)
  O3  .0250(5)  .0301(5)  .0214(4)  .0018(4)  .0055(4)  -.0009(4)
  C1  .0209(6)  .0192(6)  .0239(6)  -.0020(5)  .0080(5)  .0000(5)
  C2  .0197(6)  .0230(6)  .0252(6)  -.0010(5)  .0062(5)  .0019(5)
  C3  .0230(6)  .0210(6)  .0301(7)  -.0018(5)  .0129(5)  -.0007(5)
  C4  .0305(7)  .0230(6)  .0251(6)  -.0041(5)  .0089(5)  -.0014(5)
  C5  .0237(6)  .0254(7)  .0250(6)  -.0020(5)  .0022(5)  .0016(5)
  C6  .0206(6)  .0223(6)  .0282(7)  .0011(5)  .0079(5)  .0010(5)
  C7  .0214(6)  .0215(6)  .0261(6)  -.0009(5)  .0067(5)  -.0008(5)
  C8  .0227(6)  .0213(6)  .0249(6)  -.0018(5)  .0069(5)  -.0014(5)
  C9  .0199(6)  .0213(6)  .0250(6)  -.0005(5)  .0068(5)  -.0012(5)
  C10  .0197(6)  .0182(6)  .0232(6)  -.0022(5)  .0060(5)  -.0004(5)
  C11  .0189(6)  .0211(6)  .0262(6)  -.0001(5)  .0086(5)  -.0009(5)
  C12  .0174(6)  .0237(6)  .0256(6)  .0003(5)  .0035(5)  .0021(5)
  C13  .0220(6)  .0200(6)  .0215(6)  -.0030(5)  .0062(5)  .0000(5)
  C14  .0190(6)  .0210(6)  .0266(6)  .0000(5)  .0082(5)  .0000(5)
  C15  .0179(6)  .0209(6)  .0242(6)  -.0012(5)  .0041(5)  .0011(5)
  C16  .0294(7)  .0262(7)  .0265(7)  .0020(6)  .0103(6)  -.0010(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
  N1 C7 . . 1.286(2) no
  N1 C1 . . 1.409(2) no
  N2 O2 . . 1.2284(15) no
  N2 O1 . . 1.228(2) no
  N2 C3 . . 1.478(2) no
  O3 C13 . . 1.3651(14) no
  O3 C16 . . 1.435(2) no
  C1 C6 . . 1.399(2) no
  C1 C2 . . 1.405(2) no
  C2 C3 . . 1.382(2) no
  C2 H2 . .  .96(2) no
  C3 C4 . . 1.384(2) no
  C4 C5 . . 1.392(2) no
  C4 H4 . . 1.00(2) no
  C5 C6 . . 1.386(2) no
  C5 H5 . .  .96(2) no
  C6 H6 . .  .93(2) no
  C7 C8 . . 1.441(2) no
  C7 H7 . .  .964(15) no
  C8 C9 . . 1.348(2) no
  C8 H8 . . 1.00(2) no
  C9 C10 . . 1.459(2) no
  C9 H9 . .  .97(2) no
  C10 C15 . . 1.400(2) no
  C10 C11 . . 1.405(2) no
  C11 C12 . . 1.376(2) no
  C11 H11 . .  .94(2) no
  C12 C13 . . 1.401(2) no
  C12 H12 . .  .96(2) no
  C13 C14 . . 1.394(2) no
  C14 C15 . . 1.389(2) no
  C14 H14 . .  .99(2) no
  C15 H15 . . 1.00(2) no
  C16 H16C . .  .96(2) no
  C16 H16B . .  .99(2) no
  C16 H16A . . 1.002(15) no