data_2007333
_journal_name_full  'Acta Crystallographica'
_journal_year  1998
_journal_volume  C54
_journal_page_first  882
_journal_page_last  885
_publ_section_title
;
4-Cyano-4'-[(4R)-4,5-epoxypentyloxy]biphenyl: a Pseudosymmetry Problem Solved
with Synchrotron Data
;
loop_
_publ_author_name
  'Clegg, William'
  'Coles, Simon J.'
  'Fallis, Ian A.'
  'Griffiths, Paul M.'
  'Teat, Simon J.'
_chemical_formula_moiety  'C18 H17 N O2'
_chemical_formula_sum  'C18 H17 N O2'
_chemical_formula_weight  279.33
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21'
_symmetry_space_group_name_Hall  'P 2y1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z'
_cell_length_a  12.698(3)
_cell_length_b  5.6022(11)
_cell_length_c  21.041(4)
_cell_angle_alpha  90.00
_cell_angle_beta  106.387(4)
_cell_angle_gamma  90.00
_cell_volume  1436.0(5)
_cell_formula_units_Z  4
_cell_measurement_temperature  160(2)
_exptl_crystal_density_diffrn  1.292
_diffrn_ambient_temperature  160(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
  N1  -.16654(17)  .3465(5)  .28862(10)  .0428(6) Uani d . 1 . . N
  C1  -.1694(2)  .3312(5)  .23389(12)  .0342(6) Uani d . 1 . . C
  C2  -.16913(18)  .3209(5)  .16556(11)  .0284(6) Uani d . 1 . . C
  C3  -.1180(3)  .1326(6)  .14337(12)  .0495(8) Uani d . 1 . . C
  H3  -.0852  .0079  .1729  .059 Uiso calc R 1 . . H
  C4  -.1149(2)  .1262(6)  .07888(12)  .0470(8) Uani d . 1 . . C
  H4  -.0795  -.0039  .0644  .056 Uiso calc R 1 . . H
  C5  -.16210(17)  .3055(4)  .03399(10)  .0236(6) Uani d . 1 . . C
  C6  -.2123(2)  .4923(6)  .05755(11)  .0376(7) Uani d . 1 . . C
  H6  -.2450  .6180  .0283  .045 Uiso calc R 1 . . H
  C7  -.2156(2)  .4996(6)  .12232(11)  .0377(7) Uani d . 1 . . C
  H7  -.2505  .6296  .1372  .045 Uiso calc R 1 . . H
  C8  -.15631(17)  .3014(5)  -.03533(10)  .0242(5) Uani d . 1 . . C
  C9  -.10325(18)  .1194(5)  -.05869(10)  .0274(6) Uani d . 1 . . C
  H9  -.0700  -.0051  -.0292  .033 Uiso calc R 1 . . H
  C10  -.09667(18)  .1114(5)  -.12285(11)  .0304(6) Uani d . 1 . . C
  H10  -.0607  -.0179  -.1372  .036 Uiso calc R 1 . . H
  C11  -.14312(18)  .2940(5)  -.16627(10)  .0250(6) Uani d . 1 . . C
  O1  -.14121(12)  .3041(3)  -.23059(7)  .0306(5) Uani d . 1 . . O
  C12  -.19630(19)  .4783(5)  -.14461(10)  .0304(6) Uani d . 1 . . C
  H12  -.2289  .6032  -.1742  .037 Uiso calc R 1 . . H
  C13  -.20225(19)  .4817(5)  -.08040(11)  .0314(6) Uani d . 1 . . C
  H13  -.2388  .6106  -.0663  .038 Uiso calc R 1 . . H
  C14  -.09158(19)  .1070(5)  -.25450(10)  .0312(6) Uani d . 1 . . C
  H14A  -.1332  -.0410  -.2527  .037 Uiso calc R 1 . . H
  H14B  -.0154  .0847  -.2263  .037 Uiso calc R 1 . . H
  C15  -.0913(2)  .1557(5)  -.32462(10)  .0331(6) Uani d . 1 . . C
  H15A  -.1670  .1935  -.3514  .040 Uiso calc R 1 . . H
  H15B  -.0675  .0100  -.3434  .040 Uiso calc R 1 . . H
  C16  -.0162(2)  .3605(7)  -.32963(11)  .0425(7) Uani d . 1 . . C
  H16A  -.0459  .5088  -.3157  .051 Uiso calc R 1 . . H
  H16B  .0566  .3314  -.2978  .051 Uiso calc R 1 . . H
  C17  -.0007(2)  .4005(9)  -.39622(13)  .0610(10) Uani d . 1 . . C
  H17  .0552  .5252  -.3972  .073 Uiso calc R 1 . . H
  C18  -.0137(3)  .2274(9)  -.44527(16)  .0889(13) Uani d . 1 . . C
  H18A  -.0320  .0632  -.4346  .107 Uiso calc R 1 . . H
  H18B  .0341  .2372  -.4751  .107 Uiso calc R 1 . . H
  O2  -.09474(18)  .4069(5)  -.45104(9)  .0688(7) Uani d . 1 . . O
  N2  .32334(17)  .3588(5)  .78117(9)  .0402(6) Uani d . 1 . . N
  C19  .32279(18)  .3727(6)  .72723(11)  .0320(6) Uani d . 1 . . C
  C20  .32481(18)  .3890(5)  .65899(11)  .0295(6) Uani d . 1 . . C
  C21  .3779(3)  .5726(6)  .63809(13)  .0546(9) Uani d . 1 . . C
  H21  .4109  .6961  .6680  .066 Uiso calc R 1 . . H
  C22  .3833(3)  .5783(6)  .57363(12)  .0499(8) Uani d . 1 . . C
  H22  .4198  .7077  .5597  .060 Uiso calc R 1 . . H
  C23  .33724(17)  .4006(5)  .52861(10)  .0258(6) Uani d . 1 . . C
  C24  .2854(2)  .2166(6)  .55170(11)  .0445(8) Uani d . 1 . . C
  H24  .2532  .0912  .5222  .053 Uiso calc R 1 . . H
  C25  .2788(2)  .2086(6)  .61559(11)  .0439(8) Uani d . 1 . . C
  H25  .2426  .0793  .6298  .053 Uiso calc R 1 . . H
  C26  .34611(17)  .4027(5)  .45969(10)  .0246(6) Uani d . 1 . . C
  C27  .39925(18)  .5865(5)  .43688(10)  .0298(6) Uani d . 1 . . C
  H27  .4301  .7138  .4660  .036 Uiso calc R 1 . . H
  C28  .40851(18)  .5895(5)  .37292(10)  .0282(6) Uani d . 1 . . C
  H28  .4458  .7170  .3588  .034 Uiso calc R 1 . . H
  C29  .36354(17)  .4070(5)  .32967(10)  .0262(6) Uani d . 1 . . C
  O3  .36708(12)  .3936(4)  .26564(7)  .0305(4) Uani d . 1 . . O
  C30  .3105(2)  .2200(5)  .35134(11)  .0309(6) Uani d . 1 . . C
  H30  .2802  .0928  .3220  .037 Uiso calc R 1 . . H
  C31  .30167(19)  .2184(5)  .41507(10)  .0299(6) Uani d . 1 . . C
  H31  .2647  .0900  .4291  .036 Uiso calc R 1 . . H
  C32  .41505(19)  .5944(5)  .24138(10)  .0304(6) Uani d . 1 . . C
  H32A  .4911  .6201  .2694  .036 Uiso calc R 1 . . H
  H32B  .3720  .7406  .2429  .036 Uiso calc R 1 . . H
  C33  .41492(19)  .5428(5)  .17121(10)  .0325(7) Uani d . 1 . . C
  H33A  .3397  .4965  .1455  .039 Uiso calc R 1 . . H
  H33B  .4340  .6910  .1514  .039 Uiso calc R 1 . . H
  C34  .49278(19)  .3495(6)  .16461(10)  .0362(6) Uani d . 1 . . C
  H34A  .5645  .3745  .1980  .043 Uiso calc R 1 . . H
  H34B  .4637  .1930  .1736  .043 Uiso calc R 1 . . H
  C35  .5090(2)  .3466(6)  .09690(11)  .0406(7) Uani d . 1 . . C
  H35  .5399  .4971  .0839  .049 Uiso calc R 1 . . H
  C36  .5350(3)  .1342(7)  .06664(13)  .0595(8) Uani d . 1 . . C
  H36A  .5825  .1498  .0368  .071 Uiso calc R 1 . . H
  H36B  .5447  -.0157  .0926  .071 Uiso calc R 1 . . H
  O4  .42747(16)  .2358(5)  .04558(8)  .0657(7) Uani d . 1 . . O
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  .0558(14)  .0419(16)  .0357(11)  -.0044(14)  .0212(10)  -.0030(11)
  C1  .0391(14)  .0310(17)  .0358(13)  -.0067(14)  .0158(10)  -.0039(12)
  C2  .0295(13)  .0321(16)  .0262(11)  -.0107(12)  .0123(10)  -.0048(11)
  C3  .093(2)  .0276(17)  .0349(13)  .0107(19)  .0288(15)  .0097(13)
  C4  .086(2)  .0274(17)  .0353(13)  .0132(17)  .0303(14)  .0057(12)
  C5  .0214(11)  .0217(15)  .0279(11)  -.0059(12)  .0070(9)  -.0029(10)
  C6  .0366(14)  .0449(18)  .0285(12)  .0171(15)  .0048(10)  .0017(13)
  C7  .0321(14)  .0493(19)  .0302(12)  .0101(14)  .0062(10)  -.0098(13)
  C8  .0211(11)  .0243(15)  .0265(11)  -.0042(12)  .0058(9)  -.0017(11)
  C9  .0273(13)  .0266(14)  .0264(11)  .0059(13)  .0043(10)  .0039(11)
  C10  .0284(13)  .0309(16)  .0301(12)  .0096(14)  .0057(10)  -.0001(12)
  C11  .0201(11)  .0282(15)  .0246(10)  -.0010(12)  .0029(9)  -.0007(10)
  O1  .0341(9)  .0351(12)  .0234(7)  .0108(9)  .0091(7)  .0040(8)
  C12  .0382(14)  .0253(15)  .0300(12)  .0073(13)  .0130(11)  .0071(11)
  C13  .0400(15)  .0231(15)  .0333(12)  .0036(13)  .0141(11)  -.0011(12)
  C14  .0278(13)  .0360(16)  .0300(12)  .0068(13)  .0084(10)  -.0007(12)
  C15  .0307(13)  .0421(18)  .0269(11)  .0032(14)  .0086(10)  .0010(12)
  C16  .0391(14)  .055(2)  .0352(12)  .0009(17)  .0127(11)  .0043(14)
  C17  .0437(16)  .101(3)  .0399(14)  .0081(19)  .0141(12)  .0198(18)
  C18  .123(3)  .104(3)  .059(2)  .049(3)  .055(2)  .016(2)
  O2  .0716(14)  .0980(19)  .0377(10)  .0421(15)  .0169(10)  .0196(12)
  N2  .0546(13)  .0407(15)  .0315(10)  .0037(14)  .0223(9)  .0028(11)
  C19  .0332(13)  .0317(16)  .0340(12)  .0064(14)  .0141(10)  .0006(12)
  C20  .0283(12)  .0336(15)  .0286(11)  .0085(13)  .0113(9)  .0052(12)
  C21  .098(3)  .0350(19)  .0394(15)  -.014(2)  .0338(16)  -.0070(14)
  C22  .096(2)  .0282(17)  .0366(14)  -.0145(18)  .0361(15)  -.0045(13)
  C23  .0223(11)  .0306(16)  .0241(10)  .0060(13)  .0058(9)  .0036(11)
  C24  .0505(17)  .056(2)  .0260(12)  -.0255(18)  .0087(12)  -.0025(14)
  C25  .0468(16)  .056(2)  .0291(12)  -.0231(16)  .0110(11)  -.0009(14)
  C26  .0211(11)  .0263(15)  .0249(10)  .0047(12)  .0040(9)  .0052(11)
  C27  .0286(13)  .0349(16)  .0250(12)  -.0037(14)  .0062(10)  -.0022(12)
  C28  .0281(13)  .0321(16)  .0249(11)  -.0053(13)  .0083(9)  .0013(11)
  C29  .0246(11)  .0341(16)  .0204(10)  .0004(13)  .0070(9)  -.0001(11)
  O3  .0361(9)  .0335(12)  .0236(7)  -.0091(9)  .0112(7)  -.0021(8)
  C30  .0395(14)  .0236(15)  .0306(12)  -.0045(13)  .0118(11)  -.0038(11)
  C31  .0387(14)  .0217(14)  .0313(12)  -.0017(13)  .0135(11)  .0000(11)
  C32  .0302(13)  .0347(15)  .0272(12)  -.0063(13)  .0096(10)  .0041(11)
  C33  .0291(13)  .0440(18)  .0233(11)  -.0048(14)  .0052(10)  .0040(12)
  C34  .0344(13)  .0450(17)  .0279(11)  .0009(15)  .0069(10)  -.0028(13)
  C35  .0379(13)  .0503(17)  .0351(12)  -.0057(14)  .0126(10)  -.0048(13)
  C36  .076(2)  .063(2)  .0463(15)  -.0122(17)  .0286(15)  -.0145(15)
  O4  .0529(13)  .109(2)  .0336(9)  -.0389(14)  .0094(9)  -.0163(12)
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
  N1 C1 . 1.145(3) ?
  C1 C2 . 1.440(3) ?
  C2 C7 . 1.370(4) ?
  C2 C3 . 1.387(4) ?
  C3 C4 . 1.369(3) ?
  C4 C5 . 1.393(4) ?
  C5 C6 . 1.388(3) ?
  C5 C8 . 1.481(3) ?
  C6 C7 . 1.376(3) ?
  C8 C9 . 1.387(3) ?
  C8 C13 . 1.395(3) ?
  C9 C10 . 1.377(3) ?
  C10 C11 . 1.388(4) ?
  C11 O1 . 1.361(2) ?
  C11 C12 . 1.379(3) ?
  O1 C14 . 1.431(3) ?
  C12 C13 . 1.374(3) ?
  C14 C15 . 1.501(3) ?
  C15 C16 . 1.515(4) ?
  C16 C17 . 1.486(3) ?
  C17 C18 . 1.391(5) ?
  C17 O2 . 1.408(3) ?
  C18 O2 . 1.420(4) ?
  N2 C19 . 1.136(3) ?
  C19 C20 . 1.446(3) ?
  C20 C21 . 1.368(4) ?
  C20 C25 . 1.377(4) ?
  C21 C22 . 1.378(3) ?
  C22 C23 . 1.385(4) ?
  C23 C24 . 1.383(4) ?
  C23 C26 . 1.486(3) ?
  C24 C25 . 1.371(3) ?
  C26 C27 . 1.389(3) ?
  C26 C31 . 1.402(3) ?
  C27 C28 . 1.384(3) ?
  C28 C29 . 1.381(4) ?
  C29 O3 . 1.363(2) ?
  C29 C30 . 1.390(4) ?
  O3 C32 . 1.440(3) ?
  C30 C31 . 1.377(3) ?
  C32 C33 . 1.504(3) ?
  C33 C34 . 1.499(4) ?
  C34 C35 . 1.496(3) ?
  C35 O4 . 1.411(3) ?
  C35 C36 . 1.432(4) ?
  C36 O4 . 1.430(4) ?