data_2006657
_journal_name_full  'Acta Crystallographica'
_journal_year  1997
_journal_volume  C53
_journal_page_first  1692
_journal_page_last  1694
_publ_section_title
;
n-Butyl \a-Cyano-4-[2-(4-pyridyl)ethenyl]cinnamate
;
loop_
_publ_author_name
  'Ohhara, Takashi'
  'Hidehiro Uekusa'
  'Yuji Ohashi'
  'Shigehito Kondo'
  'Masaki Hasegawa'
_chemical_formula_moiety  'C21 H20 N2 O2'
_chemical_formula_sum  'C21 H20 N2 O2'
_chemical_formula_weight  332.401
_symmetry_cell_setting  Triclinic
_symmetry_space_group_name_H-M  'P -1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  9.072(2)
_cell_length_b  26.855(8)
_cell_length_c  8.135(2)
_cell_angle_alpha  97.419(6)
_cell_angle_beta  110.80(2)
_cell_angle_gamma  83.564(13)
_cell_volume  1832.5(9)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.2048
_diffrn_ambient_temperature  293(2)
_refine_ls_R_factor_obs  .0506
_refine_ls_wR_factor_obs  .1133
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
  O1  -.11197(14) 1.03885(5)  .8329(2)  .0718(4) Uani d . 1 . O
  O2  -.11567(12) 1.08993(4)  .63412(14)  .0525(3) Uani d . 1 . O
  O3  .77565(14)  .39779(5)  .8808(2)  .0696(4) Uani d . 1 . O
  O4  .94874(13)  .43569(4) 1.1228(2)  .0555(3) Uani d . 1 . O
  N2  .1940(2) 1.07255(6)  .5094(2)  .0799(5) Uani d . 1 . N
  N3  -.2924(2)  .78772(6)  .2280(2)  .0669(4) Uani d . 1 . N
  N4  .8657(2)  .55670(6) 1.1863(3)  .0856(6) Uani d . 1 . N
  N1 1.2807(4)  .75723(15)  .9682(5)  .0702(13) Uani d PD  .580(2) 1 N
  C1 1.2313(4)  .7988(2)  .8844(5)  .0560(12) Uani d PD  .580(2) 1 C
  C2 1.0960(4)  .82890(13)  .8806(5)  .0478(10) Uani d PD  .580(2) 1 C
  C3  .9958(3)  .81430(12)  .9587(4)  .0441(8) Uani d PD  .580(2) 1 C
  C4 1.0372(4)  .76869(13) 1.0295(5)  .0630(10) Uani d PD  .580(2) 1 C
  C5 1.1742(5)  .7412(2) 1.0231(6)  .0648(15) Uani d PD  .580(2) 1 C
  C6  .8490(3)  .84369(11)  .9559(4)  .0466(7) Uani d P  .580(2) 1 C
  C7  .7845(3)  .88541(11)  .8740(4)  .0435(7) Uani d P  .580(2) 1 C
  C8  .6308(2)  .91386(6)  .8636(2)  .0388(8) Uani d PG  .580(2) 1 C
  C9  .5752(2)  .95061(7)  .7461(3)  .0467(8) Uani d PG  .580(2) 1 C
  C10  .4319(2)  .97790(8)  .7294(3)  .0441(8) Uani d PG  .580(2) 1 C
  C11  .3442(2)  .96844(8)  .8302(3)  .0404(9) Uani d PG  .580(2) 1 C
  C12  .3999(2)  .93169(8)  .9478(3)  .0412(7) Uani d PG  .580(2) 1 C
  C13  .5432(2)  .90440(7)  .9644(2)  .0463(9) Uani d PG  .580(2) 1 C
  C2B 1.1361(5)  .8349(2)  .8664(8)  .051(2) Uani d PD  .420(2) 2 C
  C3B 1.0051(5)  .8259(2)  .9098(6)  .0397(12) Uiso d PD  .420(2) 2 C
  C4B 1.0180(7)  .7833(2)  .9920(8)  .0567(15) Uiso d PD  .420(2) 2 C
  C5B 1.1490(8)  .7491(2) 1.0213(10)  .067(2) Uani d PD  .420(2) 2 C
  N1B 1.2683(5)  .7538(2)  .9569(6)  .0461(14) Uiso d PD  .420(2) 2 N
  C1B 1.2647(6)  .7995(2)  .9033(9)  .056(2) Uani d PD  .420(2) 2 C
  C6B  .8666(5)  .8651(2)  .8738(6)  .0531(12) Uani d P  .420(2) 2 C
  C7B  .7590(5)  .8679(2)  .9459(6)  .0537(12) Uani d P  .420(2) 2 C
  C13B  .5160(3)  .89787(9) 1.0019(3)  .0450(12) Uani d PG  .420(2) 2 C
  C8B  .6162(3)  .90419(11)  .9118(4)  .0437(13) Uani d PG  .420(2) 2 C
  C9B  .5747(4)  .93991(13)  .7907(4)  .0426(11) Uani d PG  .420(2) 2 C
  C10B  .4330(4)  .96931(12)  .7597(5)  .0476(12) Uani d PG  .420(2) 2 C
  C11B  .3329(3)  .96298(12)  .8498(5)  .0421(12) Uani d PG  .420(2) 2 C
  C12B  .3743(3)  .92727(12)  .9709(4)  .0471(12) Uani d PG  .420(2) 2 C
  C14  .1838(2)  .99434(6)  .8214(2)  .0456(4) Uani d . 1 . C
  C15  .1021(2) 1.03169(6)  .7225(2)  .0431(4) Uani d . 1 . C
  C16  -.0527(2) 1.05320(6)  .7381(2)  .0470(4) Uani d . 1 . C
  C17  .1542(2) 1.05405(6)  .6038(2)  .0507(4) Uani d . 1 . C
  C18  -.2663(2) 1.11450(7)  .6414(2)  .0528(5) Uani d . 1 . C
  C19  -.3170(2) 1.15477(7)  .5162(2)  .0535(5) Uani d . 1 . C
  C20  -.4714(2) 1.18284(7)  .5172(3)  .0652(6) Uani d . 1 . C
  C21  -.5292(2) 1.22331(8)  .3896(3)  .0875(7) Uani d . 1 . C
  C22  -.1629(2)  .79362(7)  .3716(3)  .0680(6) Uani d . 1 . C
  C23  -.0532(2)  .75502(7)  .4420(3)  .0612(5) Uani d . 1 . C
  C24  -.0729(2)  .70645(6)  .3612(2)  .0484(4) Uani d . 1 . C
  C25  -.2077(2)  .70040(7)  .2130(2)  .0581(5) Uani d . 1 . C
  C26  -.3131(2)  .74110(7)  .1531(3)  .0648(6) Uani d . 1 . C
  C27  .0370(2)  .66304(6)  .4255(2)  .0542(5) Uani d . 1 . C
  C28  .1606(2)  .66219(6)  .5746(2)  .0525(5) Uani d . 1 . C
  C29  .2687(2)  .61812(6)  .6395(2)  .0473(4) Uani d . 1 . C
  C30  .3940(2)  .62352(6)  .7979(2)  .0536(5) Uani d . 1 . C
  C31  .5016(2)  .58378(6)  .8625(2)  .0550(5) Uani d . 1 . C
  C32  .4858(2)  .53594(6)  .7704(2)  .0460(4) Uani d . 1 . C
  C33  .3561(2)  .53038(6)  .6139(2)  .0515(5) Uani d . 1 . C
  C34  .2497(2)  .57023(6)  .5495(2)  .0549(5) Uani d . 1 . C
  C35  .5943(2)  .49176(6)  .8243(2)  .0500(4) Uani d . 1 . C
  C36  .7330(2)  .48567(6)  .9575(2)  .0477(4) Uani d . 1 . C
  C37  .8185(2)  .43460(7)  .9789(2)  .0517(5) Uani d . 1 . C
  C38  .8058(2)  .52533(7) 1.0844(3)  .0560(5) Uani d . 1 . C
  C39 1.0437(2)  .38808(6) 1.1622(2)  .0560(5) Uani d . 1 . C
  C40 1.1789(2)  .39830(6) 1.3311(2)  .0541(5) Uani d . 1 . C
  C41 1.2850(2)  .35120(7) 1.3892(2)  .0573(5) Uani d . 1 . C
  C42 1.4233(2)  .36141(8) 1.5612(3)  .0747(6) Uani d . 1 . C
  H1 1.2921(4)  .8082(2)  .8241(5)  .067 Uiso calc PR  .580(2) 1 H
  H2 1.0723(4)  .85865(13)  .8264(5)  .057 Uiso calc PR  .580(2) 1 H
  H4  .9738(4)  .75645(13) 1.0812(5)  .076 Uiso calc PR  .580(2) 1 H
  H5 1.1930(5)  .7090(2) 1.0600(6)  .078 Uiso calc PR  .580(2) 1 H
  H6  .7936(3)  .83210(11) 1.0183(4)  .056 Uiso calc PR  .580(2) 1 H
  H7  .8428(3)  .89806(11)  .8169(4)  .052 Uiso calc PR  .580(2) 1 H
  H9  .6338(3)  .95694(10)  .6786(3)  .056 Uiso calc PR  .580(2) 1 H
  H10  .3946(3) 1.00249(10)  .6508(4)  .053 Uiso calc PR  .580(2) 1 H
  H12  .3412(3)  .92536(11) 1.0152(4)  .049 Uiso calc PR  .580(2) 1 H
  H13  .5804(3)  .87981(9) 1.0431(3)  .056 Uiso calc PR  .580(2) 1 H
  H2B 1.1366(5)  .8637(2)  .8144(8)  .061 Uiso calc PR  .420(2) 2 H
  H4B  .9365(7)  .7772(2) 1.0292(8)  .068 Uiso calc PR  .420(2) 2 H
  H5B 1.1568(8)  .7222(2) 1.0861(10)  .080 Uiso calc PR  .420(2) 2 H
  H1B 1.3560(6)  .8081(2)  .8899(9)  .068 Uiso calc PR  .420(2) 2 H
  H6B  .8583(5)  .8885(2)  .7954(6)  .064 Uiso calc PR  .420(2) 2 H
  H7B  .7720(5)  .8450(2) 1.0272(6)  .064 Uiso calc PR  .420(2) 2 H
  H13B  .5438(3)  .87397(9) 1.0829(3)  .054 Uiso calc PR  .420(2) 2 H
  H9B  .6417(5)  .9441(2)  .7304(5)  .051 Uiso calc PR  .420(2) 2 H
  H10B  .4053(5)  .9932(2)  .6787(6)  .057 Uiso calc PR  .420(2) 2 H
  H12B  .3073(4)  .9230(2) 1.0312(6)  .057 Uiso calc PR  .420(2) 2 H
  H14  .1365(2)  .98307(6)  .8928(2)  .055 Uiso calc R 1 1 H
  H18A  -.2535(2) 1.12924(7)  .7605(2)  .063 Uiso calc R 1 . H
  H18B  -.3456(2) 1.09009(7)  .6072(2)  .063 Uiso calc R 1 . H
  H19A  -.3296(2) 1.13956(7)  .3976(2)  .064 Uiso calc R 1 . H
  H19B  -.2354(2) 1.17838(7)  .5497(2)  .064 Uiso calc R 1 . H
  H20A  -.4575(2) 1.19835(7)  .6358(3)  .078 Uiso calc R 1 . H
  H20B  -.5516(2) 1.15890(7)  .4869(3)  .078 Uiso calc R 1 . H
  H21A  -.6268(2) 1.23966(8)  .3963(3)  .131 Uiso calc R 1 . H
  H21B  -.5457(2) 1.20817(8)  .2715(3)  .131 Uiso calc R 1 . H
  H21C  -.4515(2) 1.24765(8)  .4204(3)  .131 Uiso calc R 1 . H
  H22  -.1455(2)  .82594(7)  .4280(3)  .082 Uiso calc R 1 . H
  H23  .0337(2)  .76169(7)  .5434(3)  .073 Uiso calc R 1 . H
  H25  -.2277(2)  .66859(7)  .1531(2)  .070 Uiso calc R 1 . H
  H26  -.4033(2)  .73532(7)  .0548(3)  .078 Uiso calc R 1 . H
  H27  .0179(2)  .63281(6)  .3541(2)  .065 Uiso calc R 1 . H
  H28  .1812(2)  .69251(6)  .6452(2)  .063 Uiso calc R 1 . H
  H30  .4061(2)  .65487(6)  .8629(2)  .064 Uiso calc R 1 . H
  H31  .5853(2)  .58899(6)  .9682(2)  .066 Uiso calc R 1 . H
  H33  .3411(2)  .49877(6)  .5510(2)  .062 Uiso calc R 1 . H
  H34  .1645(2)  .56502(6)  .4451(2)  .066 Uiso calc R 1 . H
  H35  .5615(2)  .46223(6)  .7530(2)  .060 Uiso calc R 1 . H
  H39A 1.0830(2)  .37545(6) 1.0672(2)  .067 Uiso calc R 1 . H
  H39B  .9802(2)  .36312(6) 1.1753(2)  .067 Uiso calc R 1 . H
  H40A 1.1374(2)  .41227(6) 1.4233(2)  .065 Uiso calc R 1 . H
  H40B 1.2412(2)  .42320(6) 1.3154(2)  .065 Uiso calc R 1 . H
  H41A 1.3262(2)  .33721(7) 1.2968(2)  .069 Uiso calc R 1 . H
  H41B 1.2227(2)  .32634(7) 1.4050(2)  .069 Uiso calc R 1 . H
  H42A 1.4865(2)  .33061(8) 1.5921(3)  .112 Uiso calc R 1 . H
  H42B 1.3833(2)  .37459(8) 1.6539(3)  .112 Uiso calc R 1 . H
  H42C 1.4868(2)  .38546(8) 1.5457(3)  .112 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  .0665(7)  .0841(9)  .0825(8)  .0222(6)  .0436(6)  .0437(7)
  O2  .0482(5)  .0596(7)  .0504(6)  .0150(5)  .0188(5)  .0189(6)
  O3  .0746(8)  .0481(7)  .0686(9)  .0032(6)  .0088(7)  -.0036(7)
  O4  .0611(6)  .0426(6)  .0551(7)  .0066(5)  .0128(6)  .0073(5)
  N2  .0917(10)  .0784(11)  .0935(11)  .0231(9)  .0582(8)  .0418(9)
  N3  .0690(9)  .0590(10)  .0804(10)  .0132(7)  .0347(8)  .0238(8)
  N4  .0834(11)  .0511(10)  .0878(13)  -.0020(8)  -.0089(10)  -.0015(9)
  N1  .0440(14)  .067(2)  .092(2)  .0061(13)  .0222(14)  -.009(2)
  C1  .041(2)  .073(3)  .061(2)  -.008(2)  .0260(15)  .004(2)
  C2  .040(2)  .043(2)  .062(2)  -.0137(13)  .0153(14)  .0095(14)
  C3  .0456(14)  .042(2)  .047(2)  .0013(12)  .0189(12)  .0073(14)
  C4  .063(2)  .051(2)  .085(2)  .010(2)  .037(2)  .021(2)
  C5  .066(2)  .055(2)  .060(2)  .016(2)  .013(2)  .003(2)
  C6  .0495(14)  .041(2)  .054(2)  .0084(12)  .0233(13)  .0139(13)
  C7  .0450(14)  .039(2)  .050(2)  .0017(12)  .0218(13)  .0071(13)
  C8  .0411(13)  .044(2)  .0345(15)  -.0013(12)  .0169(11)  .0049(13)
  C9  .055(2)  .048(2)  .050(2)  .0079(13)  .0316(13)  .0179(14)
  C10  .0490(15)  .041(2)  .051(2)  .0105(12)  .0266(12)  .0202(13)
  C11  .056(2)  .031(2)  .0328(15)  .0062(13)  .0108(13)  .0174(12)
  C12  .0423(13)  .040(2)  .052(2)  -.0038(12)  .0251(12)  .0163(13)
  C13  .061(2)  .040(2)  .043(2)  -.0054(14)  .0193(14)  .0165(13)
  C2B  .028(2)  .046(3)  .075(3)  -.013(2)  .013(2)  .000(2)
  C5B  .073(4)  .048(3)  .093(4)  -.004(3)  .043(3)  .015(3)
  C1B  .031(2)  .048(3)  .079(4)  -.003(2)  .007(2)  -.001(3)
  C6B  .067(3)  .043(3)  .051(2)  .002(2)  .020(2)  .014(2)
  C7B  .065(3)  .043(3)  .055(3)  .000(2)  .021(2)  .016(2)
  C13B  .051(2)  .032(2)  .050(2)  .006(2)  .012(2)  .020(2)
  C8B  .060(3)  .030(2)  .038(2)  .007(2)  .014(2)  .014(2)
  C9B  .043(2)  .057(3)  .039(2)  .009(2)  .025(2)  .025(2)
  C10B  .075(3)  .041(2)  .037(2)  .004(2)  .027(2)  .021(2)
  C11B  .038(2)  .042(3)  .066(3)  -.016(2)  .041(2)  -.008(2)
  C12B  .057(2)  .042(2)  .048(2)  -.001(2)  .020(2)  .021(2)
  C14  .0474(8)  .0433(9)  .0490(9)  .0015(7)  .0199(7)  .0097(7)
  C15  .0451(8)  .0430(9)  .0422(9)  .0000(7)  .0168(7)  .0056(7)
  C16  .0469(8)  .0494(10)  .0431(9)  .0072(7)  .0146(7)  .0102(8)
  C17  .0549(9)  .0470(10)  .0541(10)  .0111(7)  .0244(8)  .0147(8)
  C18  .0450(8)  .0621(11)  .0487(10)  .0136(8)  .0173(7)  .0082(8)
  C19  .0500(9)  .0535(10)  .0539(10)  .0087(8)  .0168(8)  .0080(8)
  C20  .0594(10)  .0634(12)  .0679(12)  .0190(9)  .0232(9)  .0050(10)
  C21  .0733(12)  .0599(13)  .124(2)  .0263(10)  .0310(12)  .0251(13)
  C22  .0844(12)  .0445(11)  .0787(13)  .0068(9)  .0350(10)  .0090(10)
  C23  .0706(11)  .0491(11)  .0595(11)  .0014(9)  .0185(9)  .0067(9)
  C24  .0533(8)  .0420(9)  .0531(10)  -.0012(7)  .0217(7)  .0083(8)
  C25  .0552(9)  .0506(10)  .0650(12)  -.0042(8)  .0156(9)  .0085(9)
  C26  .0524(10)  .0645(12)  .0758(13)  .0047(9)  .0181(9)  .0207(10)
  C27  .0579(9)  .0419(10)  .0591(11)  -.0006(8)  .0170(8)  .0035(8)
  C28  .0583(9)  .0404(9)  .0567(10)  -.0018(7)  .0189(8)  .0016(8)
  C29  .0490(8)  .0424(9)  .0504(10)  -.0013(7)  .0183(7)  .0032(8)
  C30  .0570(9)  .0396(9)  .0572(11)  -.0020(8)  .0143(8)  -.0031(8)
  C31  .0579(9)  .0456(10)  .0503(10)  -.0023(8)  .0074(8)  -.0010(8)
  C32  .0497(8)  .0418(9)  .0464(9)  -.0020(7)  .0167(7)  .0046(7)
  C33  .0533(9)  .0401(9)  .0552(10)  -.0030(7)  .0144(8)  -.0037(8)
  C34  .0536(9)  .0492(10)  .0521(11)  -.0021(8)  .0085(8)  -.0005(8)
  C35  .0597(9)  .0410(9)  .0467(10)  -.0041(7)  .0159(8)  .0014(8)
  C36  .0544(8)  .0412(9)  .0474(9)  -.0025(7)  .0176(7)  .0044(7)
  C37  .0581(9)  .0465(10)  .0477(10)  -.0019(8)  .0157(8)  .0040(8)
  C38  .0567(9)  .0431(10)  .0587(11)  .0027(8)  .0083(8)  .0105(9)
  C39  .0645(10)  .0403(9)  .0604(11)  .0057(8)  .0194(8)  .0101(8)
  C40  .0546(9)  .0454(10)  .0622(11)  -.0011(7)  .0198(8)  .0089(8)
  C41  .0556(9)  .0499(10)  .0640(11)  .0009(8)  .0176(8)  .0091(9)
  C42  .0639(11)  .0700(14)  .0777(14)  .0013(10)  .0110(10)  .0076(11)
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 C16 . 1.204(2) ?
  O2 C16 . 1.327(2) ?
  O2 C18 . 1.467(2) ?
  O3 C37 . 1.195(2) ?
  O4 C37 . 1.336(2) ?
  O4 C39 . 1.464(2) ?
  N2 C17 . 1.142(2) ?
  N3 C26 . 1.322(2) ?
  N3 C22 . 1.338(2) ?
  N4 C38 . 1.138(2) ?
  N1 C5 . 1.329(7) ?
  N1 C1 . 1.333(6) ?
  C1 C2 . 1.385(5) ?
  C2 C3 . 1.392(5) ?
  C3 C4 . 1.378(5) ?
  C3 C6 . 1.464(4) ?
  C4 C5 . 1.386(5) ?
  C6 C7 . 1.346(4) ?
  C6 C15 2_677 3.936(3) ?
  C7 C8 . 1.493(3) ?
  C7 C14 2_677 3.780(3) ?
  C8 C9 . 1.39 ?
  C8 C13 . 1.39 ?
  C9 C10 . 1.39 ?
  C10 C11 . 1.39 ?
  C11 C12 . 1.39 ?
  C11 C14 . 1.523(2) ?
  C12 C13 . 1.39 ?
  C2B C1B . 1.389(7) ?
  C2B C3B . 1.407(7) ?
  C3B C4B . 1.372(7) ?
  C3B C6B . 1.514(6) ?
  C4B C5B . 1.387(8) ?
  C5B N1B . 1.383(9) ?
  N1B C1B . 1.348(8) ?
  C6B C7B . 1.297(7) ?
  C7B C8B . 1.496(5) ?
  C13B C8B . 1.39 ?
  C13B C12B . 1.39 ?
  C8B C9B . 1.39 ?
  C9B C10B . 1.39 ?
  C10B C11B . 1.39 ?
  C11B C12B . 1.39 ?
  C11B C14 . 1.471(3) ?
  C14 C15 . 1.350(2) ?
  C14 C7 2_677 3.780(3) yes
  C14 C15 2_576 4.273(3) yes
  C15 C17 . 1.433(2) ?
  C15 C16 . 1.499(2) ?
  C15 C6 2_677 3.936(3) yes
  C15 C14 2_576 4.273(3) yes
  C18 C19 . 1.503(2) ?
  C19 C20 . 1.516(2) ?
  C20 C21 . 1.520(3) ?
  C22 C23 . 1.382(2) ?
  C23 C24 . 1.383(2) ?
  C24 C25 . 1.387(2) ?
  C24 C27 . 1.467(2) ?
  C25 C26 . 1.385(2) ?
  C27 C28 . 1.329(2) ?
  C28 C29 . 1.474(2) ?
  C29 C30 . 1.386(2) ?
  C29 C34 . 1.392(2) ?
  C30 C31 . 1.384(2) ?
  C31 C32 . 1.396(2) ?
  C32 C33 . 1.398(2) ?
  C32 C35 . 1.461(2) ?
  C33 C34 . 1.381(2) ?
  C35 C36 . 1.348(2) ?
  C35 C36 2_667 3.925(3) yes
  C35 C36 2_767 5.798(3) yes
  C36 C38 . 1.423(2) ?
  C36 C37 . 1.496(2) ?
  C36 C35 2_667 3.925(3) yes
  C36 C35 2_767 5.798(3) yes
  C39 C40 . 1.500(2) ?
  C40 C41 . 1.519(2) ?
  C41 C42 . 1.529(3) ?