data_2008220
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  446
_journal_page_last  450
_publ_section_title
;
 Bond-length alternation in rigidized merocyanines
;
loop_
_publ_author_name
  'Lawrentz, Ulf'
  'Grahn, Walter'
  'Dix, Ina'
  'Jones*, Peter G.'
_chemical_formula_sum  'C22 H25 N O'
_chemical_formula_weight  319.43
_chemical_melting_point  267
_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  7.733(2)
_cell_length_b  6.295(2)
_cell_length_c  34.222(5)
_cell_angle_alpha  90.00
_cell_angle_beta  95.32(3)
_cell_angle_gamma  90.00
_cell_volume  1658.6(7)
_cell_formula_units_Z  4
_cell_measurement_temperature  143(2)
_exptl_crystal_density_diffrn  1.279
_diffrn_ambient_temperature  143(2)
_refine_ls_R_factor_obs  0.0637
_refine_ls_wR_factor_obs  0.1177
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
  O 0.7537(4) 0.7318(4) 0.45504(7) 0.0627(8) Uani d U 1 . O
  N 0.3619(3) 0.5719(4) 0.06262(7) 0.0368(7) Uani d U 1 . N
  C1 0.6969(4) 0.6233(5) 0.38960(9) 0.0348(8) Uani d U 1 . C
  H1 0.7667 0.7341 0.3806 0.042 Uiso calc R 1 . H
  C2 0.6831(4) 0.6052(6) 0.43150(10) 0.0416(9) Uani d U 1 . C
  C3 0.5749(4) 0.4245(6) 0.44507(9) 0.0472(9) Uani d U 1 . C
  H3A 0.4562 0.4769 0.4481 0.057 Uiso calc R 1 . H
  H3B 0.6259 0.3755 0.4711 0.057 Uiso calc R 1 . H
  C4 0.5638(4) 0.2381(6) 0.41693(9) 0.0418(9) Uani d U 1 . C
  H4A 0.4800 0.1330 0.4255 0.050 Uiso calc R 1 . H
  H4B 0.6788 0.1685 0.4177 0.050 Uiso calc R 1 . H
  C4A 0.5071(4) 0.3059(5) 0.37514(9) 0.0346(8) Uani d U 1 . C
  H4A1 0.3845 0.3570 0.3747 0.042 Uiso calc R 1 . H
  C5 0.4756(4) 0.0231(5) 0.27404(9) 0.0312(7) Uani d U 1 . C
  H5A 0.4088 -0.1040 0.2806 0.037 Uiso calc R 1 . H
  H5B 0.5997 -0.0172 0.2753 0.037 Uiso calc R 1 . H
  C6 0.4155(4) 0.0931(5) 0.23267(9) 0.0306(7) Uani d U 1 . C
  H6A 0.4569 -0.0109 0.2139 0.037 Uiso calc R 1 . H
  H6B 0.2870 0.0926 0.2293 0.037 Uiso calc R 1 . H
  C7 0.4795(4) 0.3113(5) 0.22277(9) 0.0258(7) Uani d U 1 . C
  C8 0.5484(3) 0.4377(5) 0.25186(8) 0.0242(7) Uani d U 1 . C
  H8 0.6010 0.5664 0.2446 0.029 Uiso calc R 1 . H
  C8A 0.5486(3) 0.3928(5) 0.29321(9) 0.0252(7) Uani d U 1 . C
  C9 0.6260(4) 0.5220(5) 0.32139(9) 0.0268(7) Uani d U 1 . C
  H9 0.6907 0.6399 0.3133 0.032 Uiso calc R 1 . H
  C9A 0.6158(4) 0.4909(5) 0.36263(9) 0.0282(7) Uani d U 1 . C
  C10 0.5089(4) 0.1271(5) 0.34586(9) 0.0333(8) Uani d U 1 . C
  H10A 0.4306 0.0129 0.3535 0.040 Uiso calc R 1 . H
  H10B 0.6278 0.0677 0.3469 0.040 Uiso calc R 1 . H
  C10A 0.4527(4) 0.1952(5) 0.30402(8) 0.0278(7) Uani d U 1 . C
  H10C 0.3262 0.2309 0.3026 0.033 Uiso calc R 1 . H
  C1' 0.3965(4) 0.5062(5) 0.10082(9) 0.0299(7) Uani d U 1 . C
  C2' 0.4831(4) 0.6376(5) 0.12957(9) 0.0299(7) Uani d U 1 . C
  H2' 0.5234 0.7731 0.1222 0.036 Uiso calc R 1 . H
  C3' 0.5108(4) 0.5739(5) 0.16817(9) 0.0275(7) Uani d U 1 . C
  H3' 0.5691 0.6679 0.1867 0.033 Uiso calc R 1 . H
  C4' 0.4567(3) 0.3772(5) 0.18115(9) 0.0253(7) Uani d U 1 . C
  C2" 0.3428(4) 0.3076(5) 0.11354(9) 0.0331(8) Uani d U 1 . C
  H2" 0.2838 0.2134 0.0951 0.040 Uiso calc R 1 . H
  C3" 0.3736(4) 0.2458(5) 0.15226(9) 0.0308(7) Uani d U 1 . C
  H3" 0.3368 0.1086 0.1596 0.037 Uiso calc R 1 . H
  C1"' 0.2945(5) 0.4207(6) 0.03279(9) 0.0465(9) Uani d U 1 . C
  H1"1 0.3754 0.3014 0.0320 0.056 Uiso calc R 1 . H
  H1"2 0.2814 0.4910 0.0071 0.056 Uiso calc R 1 . H
  H1"3 0.1813 0.3680 0.0392 0.056 Uiso calc R 1 . H
  C2"' 0.4245(4) 0.7739(5) 0.04965(10) 0.0434(9) Uani d U 1 . C
  H2"1 0.3957 0.8856 0.0679 0.052 Uiso calc R 1 . H
  H2"2 0.3696 0.8058 0.0234 0.052 Uiso calc R 1 . H
  H2"3 0.5508 0.7672 0.0489 0.052 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
  O 0.094(2) 0.0569(18) 0.0337(15) -0.0017(16) -0.0123(14) -0.0074(14)
  N 0.0474(16) 0.0325(16) 0.0298(15) -0.0005(14) 0.0004(13) -0.0011(13)
  C1 0.0410(18) 0.0315(18) 0.0312(17) 0.0049(16) -0.0001(15) 0.0023(16)
  C2 0.050(2) 0.041(2) 0.0319(19) 0.0120(18) -0.0036(16) 0.0000(18)
  C3 0.046(2) 0.068(3) 0.0288(19) 0.0091(19) 0.0049(16) 0.0067(19)
  C4 0.0403(19) 0.050(2) 0.0349(19) -0.0058(18) 0.0047(15) 0.0115(18)
  C4A 0.0327(17) 0.043(2) 0.0284(17) 0.0004(15) 0.0022(14) 0.0080(16)
  C5 0.0329(16) 0.0207(16) 0.0400(19) -0.0013(14) 0.0028(15) 0.0044(15)
  C6 0.0320(16) 0.0227(16) 0.0367(18) -0.0010(14) 0.0016(14) -0.0029(15)
  C7 0.0236(15) 0.0230(16) 0.0309(17) 0.0002(13) 0.0041(13) -0.0004(14)
  C8 0.0223(14) 0.0203(16) 0.0305(17) 0.0000(13) 0.0041(13) 0.0008(14)
  C8A 0.0231(15) 0.0221(16) 0.0305(17) 0.0029(13) 0.0041(13) 0.0027(14)
  C9 0.0310(16) 0.0176(16) 0.0319(17) -0.0018(13) 0.0026(13) 0.0018(14)
  C9A 0.0278(15) 0.0293(17) 0.0269(16) 0.0086(14) -0.0002(13) 0.0024(14)
  C10 0.0323(17) 0.0306(19) 0.0369(18) -0.0064(15) 0.0029(14) 0.0082(16)
  C10A 0.0276(16) 0.0251(16) 0.0308(17) -0.0009(13) 0.0040(13) 0.0046(14)
  C1' 0.0322(16) 0.0328(18) 0.0250(16) 0.0030(15) 0.0049(14) 0.0001(15)
  C2' 0.0314(16) 0.0281(18) 0.0311(18) -0.0017(14) 0.0073(14) -0.0007(15)
  C3' 0.0274(15) 0.0276(17) 0.0275(17) -0.0029(14) 0.0029(13) -0.0046(15)
  C4' 0.0234(15) 0.0256(17) 0.0274(16) 0.0010(13) 0.0047(13) -0.0040(14)
  C2" 0.0410(18) 0.0259(17) 0.0321(18) -0.0022(15) 0.0017(15) -0.0060(15)
  C3" 0.0367(17) 0.0246(17) 0.0314(17) -0.0006(15) 0.0053(14) -0.0036(15)
  C1"' 0.065(2) 0.043(2) 0.0299(19) -0.002(2) -0.0044(17) -0.0030(18)
  C2"' 0.053(2) 0.043(2) 0.034(2) -0.0049(18) 0.0017(17) 0.0028(18)
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
  O C2 . 1.225(4) ?
  N C1' . 1.374(4) Y
  N C2"' . 1.445(4) ?
  N C1"' . 1.456(4) ?
  C1 C9A . 1.354(4) Y
  C1 C2 . 1.452(4) Y
  C2 C3 . 1.510(5) ?
  C3 C4 . 1.515(5) ?
  C4 C4A . 1.518(4) ?
  C4A C10 . 1.508(4) ?
  C4A C9A . 1.521(4) ?
  C5 C10A . 1.514(4) ?
  C5 C6 . 1.514(4) ?
  C6 C7 . 1.509(4) ?
  C7 C8 . 1.345(4) Y
  C7 C4' . 1.478(4) Y
  C8 C8A . 1.443(4) Y
  C8A C9 . 1.358(4) Y
  C8A C10A . 1.511(4) ?
  C9 C9A . 1.434(4) Y
  C10 C10A . 1.519(4) ?
  C1' C2" . 1.399(4) Y
  C1' C2' . 1.407(4) Y
  C2' C3' . 1.378(4) Y
  C3' C4' . 1.392(4) Y
  C4' C3" . 1.399(4) Y
  C2" C3" . 1.380(4) Y