#------------------------------------------------------------------------------
#$Date: 2008-01-26 14:05:32 +0100 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012788.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2012788
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o389
_journal_page_last  o393
_publ_section_title
;
Structural properties of a series of photochromic fluorinated indolylfulgides
;
loop_
_publ_author_name
  'Wolak, Mason A.'
  'Finn, Robert C.'
  'Rarig Jr, Randy S.'
  'Thomas, Craig J.'
  'Hammond, Robert P.'
  'Birge, Robert R.'
  'Zubieta, Jon'
  'Lees, Watson J.'
_chemical_formula_sum  'C26 H24 F3 N O3'
_chemical_formula_weight  455.46
_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  7.7210(10)
_cell_length_b  20.737(2)
_cell_length_c  13.4960(10)
_cell_angle_alpha  90
_cell_angle_beta  99.350(10)
_cell_angle_gamma  90
_cell_volume  2132.1(4)
_cell_formula_units_Z  4
_cell_measurement_temperature  90(2)
_exptl_crystal_density_diffrn  1.419
_diffrn_ambient_temperature  293(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
  F1 0.14714(17) 0.09928(7) -0.10374(9) 0.0263(3) Uani d . 1 . . F
  F2 0.41207(18) 0.07228(7) -0.11760(9) 0.0295(3) Uani d . 1 . . F
  F3 0.3423(2) 0.17173(7) -0.10914(9) 0.0330(4) Uani d . 1 . . F
  O1 0.2247(2) -0.02341(8) -0.03207(11) 0.0292(4) Uani d . 1 . . O
  O2 0.2026(2) -0.03651(7) 0.12990(11) 0.0217(3) Uani d . 1 . . O
  O3 0.2305(2) -0.03111(7) 0.29719(11) 0.0231(3) Uani d . 1 . . O
  C1 0.5495(3) 0.21715(10) 0.07583(14) 0.0174(4) Uani d . 1 . . C
  C2 0.6910(3) 0.21212(11) 0.02387(16) 0.0221(4) Uani d . 1 . . C
  H1 0.7025 0.1766 -0.0167 0.027 Uiso calc R 1 . . H
  C3 0.8137(3) 0.26134(11) 0.03428(17) 0.0253(5) Uani d . 1 . . C
  H2 0.9087 0.2589 0.0000 0.030 Uiso calc R 1 . . H
  C4 0.7974(3) 0.31510(11) 0.09593(16) 0.0249(5) Uani d . 1 . . C
  H3 0.8822 0.3473 0.1016 0.030 Uiso calc R 1 . . H
  C5 0.6599(3) 0.32104(10) 0.14772(15) 0.0223(4) Uani d . 1 . . C
  H4 0.6499 0.3565 0.1886 0.027 Uiso calc R 1 . . H
  C6 0.5357(3) 0.27182(10) 0.13662(15) 0.0195(4) Uani d . 1 . . C
  C7 0.3325(3) 0.30971(11) 0.25344(18) 0.0290(5) Uani d . 1 . . C
  H7A 0.2091 0.3042 0.2539 0.044 Uiso calc R 1 . . H
  H7B 0.3544 0.3529 0.2332 0.044 Uiso calc R 1 . . H
  H7C 0.3962 0.3020 0.3196 0.044 Uiso calc R 1 . . H
  C8 0.3146(3) 0.20524(10) 0.15613(15) 0.0180(4) Uani d . 1 . . C
  C9 0.1579(3) 0.18219(11) 0.19753(17) 0.0248(5) Uani d . 1 . . C
  H9A 0.1926 0.1698 0.2664 0.037 Uiso calc R 1 . . H
  H9B 0.1077 0.1457 0.1594 0.037 Uiso calc R 1 . . H
  H9C 0.0727 0.2162 0.1934 0.037 Uiso calc R 1 . . H
  C10 0.4078(3) 0.17502(9) 0.08963(14) 0.0164(4) Uani d . 1 . . C
  C11 0.3630(3) 0.11204(10) 0.04251(15) 0.0168(4) Uani d . 1 . . C
  C12 0.3493(3) 0.05692(9) 0.09420(14) 0.0156(4) Uani d . 1 . . C
  C13 0.2561(3) -0.00294(10) 0.05117(16) 0.0200(4) Uani d . 1 . . C
  C14 0.2698(3) -0.00862(9) 0.22235(15) 0.0173(4) Uani d . 1 . . C
  C15 0.3888(3) 0.04474(9) 0.20366(14) 0.0146(4) Uani d . 1 . . C
  C16 0.5299(3) 0.06242(9) 0.27210(14) 0.0140(4) Uani d . 1 . . C
  C17 0.6847(3) 0.09922(9) 0.24674(14) 0.0153(4) Uani d . 1 . . C
  H22 0.6650 0.1107 0.1753 0.018 Uiso calc R 1 . . H
  C18 0.7123(3) 0.16085(10) 0.31196(15) 0.0197(4) Uani d . 1 . . C
  H21A 0.8131 0.1845 0.2967 0.024 Uiso calc R 1 . . H
  H21B 0.6099 0.1885 0.2972 0.024 Uiso calc R 1 . . H
  C19 0.7422(3) 0.14206(10) 0.42377(15) 0.0213(4) Uani d . 1 . . C
  H20 0.7582 0.1810 0.4653 0.026 Uiso calc R 1 . . H
  C20 0.5818(3) 0.10477(10) 0.44576(15) 0.0207(4) Uani d . 1 . . C
  H19A 0.4783 0.1318 0.4309 0.025 Uiso calc R 1 . . H
  H19B 0.5978 0.0936 0.5164 0.025 Uiso calc R 1 . . H
  C21 0.5548(3) 0.04270(10) 0.38175(14) 0.0164(4) Uani d . 1 . . C
  H18 0.4516 0.0191 0.3959 0.020 Uiso calc R 1 . . H
  C22 0.7197(3) 0.00052(10) 0.40592(15) 0.0183(4) Uani d . 1 . . C
  H24A 0.7372 -0.0118 0.4762 0.022 Uiso calc R 1 . . H
  H24B 0.7048 -0.0385 0.3657 0.022 Uiso calc R 1 . . H
  C23 0.8799(3) 0.03771(10) 0.38364(15) 0.0186(4) Uani d . 1 . . C
  H26 0.9847 0.0105 0.3987 0.022 Uiso calc R 1 . . H
  C24 0.9053(3) 0.09909(10) 0.44753(15) 0.0218(4) Uani d . 1 . . C
  H25A 1.0076 0.1224 0.4335 0.026 Uiso calc R 1 . . H
  H25B 0.9248 0.0878 0.5182 0.026 Uiso calc R 1 . . H
  C25 0.8486(3) 0.05553(10) 0.27145(14) 0.0175(4) Uani d . 1 . . C
  H23A 0.8317 0.0166 0.2312 0.021 Uiso calc R 1 . . H
  H23B 0.9505 0.0779 0.2550 0.021 Uiso calc R 1 . . H
  C26 0.3164(3) 0.11332(10) -0.07177(15) 0.0208(4) Uani d . 1 . . C
  N1 0.3896(2) 0.26411(8) 0.18304(13) 0.0193(4) Uani d . 1 . . N
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
  F1 0.0211(6) 0.0333(7) 0.0217(6) -0.0024(5) -0.0051(5) 0.0007(5)
  F2 0.0302(7) 0.0400(8) 0.0186(6) 0.0059(6) 0.0044(5) -0.0045(6)
  F3 0.0508(9) 0.0262(7) 0.0186(6) -0.0121(6) -0.0046(6) 0.0066(5)
  O1 0.0401(10) 0.0238(8) 0.0217(8) -0.0050(7) -0.0013(7) -0.0051(6)
  O2 0.0214(7) 0.0190(7) 0.0242(7) -0.0055(6) 0.0025(6) -0.0020(6)
  O3 0.0233(8) 0.0217(8) 0.0262(8) -0.0031(6) 0.0093(6) 0.0028(6)
  C1 0.0203(10) 0.0154(9) 0.0153(9) -0.0020(8) -0.0010(7) 0.0038(7)
  C2 0.0252(11) 0.0214(10) 0.0198(10) -0.0011(8) 0.0040(8) 0.0030(8)
  C3 0.0248(11) 0.0279(12) 0.0250(11) -0.0032(9) 0.0092(9) 0.0042(9)
  C4 0.0282(12) 0.0219(11) 0.0236(10) -0.0079(9) 0.0015(9) 0.0036(8)
  C5 0.0308(12) 0.0168(10) 0.0179(10) -0.0034(8) -0.0001(8) 0.0023(8)
  C6 0.0247(11) 0.0154(9) 0.0170(9) 0.0011(8) -0.0014(8) 0.0033(7)
  C7 0.0368(13) 0.0194(11) 0.0315(12) 0.0028(9) 0.0079(10) -0.0045(9)
  C8 0.0199(10) 0.0160(9) 0.0172(9) 0.0022(8) 0.0002(8) 0.0028(7)
  C9 0.0230(11) 0.0258(11) 0.0263(11) 0.0045(9) 0.0062(9) 0.0012(9)
  C10 0.0184(10) 0.0161(9) 0.0133(8) -0.0002(7) -0.0015(7) 0.0023(7)
  C11 0.0152(9) 0.0184(10) 0.0165(9) 0.0005(7) 0.0014(7) -0.0013(7)
  C12 0.0143(9) 0.0156(9) 0.0168(9) -0.0003(7) 0.0023(7) -0.0021(7)
  C13 0.0193(10) 0.0168(10) 0.0229(10) 0.0000(8) 0.0007(8) 0.0000(8)
  C14 0.0130(9) 0.0157(9) 0.0231(10) 0.0013(7) 0.0031(8) 0.0014(8)
  C15 0.0153(9) 0.0129(9) 0.0166(9) 0.0003(7) 0.0052(7) 0.0009(7)
  C16 0.0156(9) 0.0126(9) 0.0147(8) 0.0019(7) 0.0052(7) -0.0004(7)
  C17 0.0161(9) 0.0159(9) 0.0137(8) -0.0021(7) 0.0020(7) 0.0030(7)
  C18 0.0230(10) 0.0161(10) 0.0186(9) -0.0019(8) -0.0008(8) 0.0007(8)
  C19 0.0283(11) 0.0182(10) 0.0156(9) 0.0011(8) -0.0014(8) -0.0024(8)
  C20 0.0254(11) 0.0229(10) 0.0142(9) 0.0066(8) 0.0037(8) -0.0015(8)
  C21 0.0176(10) 0.0189(10) 0.0137(9) -0.0011(7) 0.0053(7) 0.0029(7)
  C22 0.0212(10) 0.0173(9) 0.0166(9) 0.0020(8) 0.0034(8) 0.0027(7)
  C23 0.0170(10) 0.0211(10) 0.0173(9) 0.0035(8) 0.0020(8) 0.0022(8)
  C24 0.0234(11) 0.0233(11) 0.0168(9) -0.0033(8) -0.0022(8) 0.0028(8)
  C25 0.0159(10) 0.0208(10) 0.0166(9) 0.0011(8) 0.0049(7) 0.0023(8)
  C26 0.0213(10) 0.0209(10) 0.0188(9) -0.0010(8) -0.0007(8) 0.0003(8)
  N1 0.0213(9) 0.0174(8) 0.0193(8) 0.0013(7) 0.0036(7) 0.0003(7)
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
  F1 C26 . 1.340(2) no
  F2 C26 . 1.342(3) no
  F3 C26 . 1.339(2) no
  O1 C13 . 1.188(3) no
  O2 C13 . 1.388(3) no
  O2 C14 . 1.396(2) no
  O3 C14 . 1.196(3) no
  C1 C2 . 1.394(3) no
  C1 C6 . 1.413(3) no
  C1 C10 . 1.435(3) no
  C2 C3 . 1.385(3) no
  C2 H1 . 0.9300 no
  C3 C4 . 1.409(3) no
  C3 H2 . 0.9300 no
  C4 C5 . 1.368(3) no
  C4 H3 . 0.9300 no
  C5 C6 . 1.392(3) no
  C5 H4 . 0.9300 no
  C6 N1 . 1.385(3) no
  C7 N1 . 1.459(3) no
  C7 H7A . 0.9600 no
  C7 H7B . 0.9600 no
  C7 H7C . 0.9600 no
  C8 N1 . 1.375(3) no
  C8 C10 . 1.388(3) no
  C8 C9 . 1.491(3) no
  C9 H9A . 0.9600 no
  C9 H9B . 0.9600 no
  C9 H9C . 0.9600 no
  C10 C11 . 1.469(3) no
  C11 C12 . 1.352(3) no
  C11 C26 . 1.526(3) no
  C12 C15 . 1.481(3) no
  C12 C13 . 1.503(3) no
  C14 C15 . 1.485(3) no
  C15 C16 . 1.359(3) no
  C16 C17 . 1.504(3) no
  C16 C21 . 1.517(3) no
  C17 C18 . 1.547(3) no
  C17 C25 . 1.548(3) no
  C17 H22 . 0.9800 no
  C18 C19 . 1.539(3) no
  C18 H21A . 0.9700 no
  C18 H21B . 0.9700 no
  C19 C20 . 1.529(3) no
  C19 C24 . 1.534(3) no
  C19 H20 . 0.9800 no
  C20 C21 . 1.545(3) no
  C20 H19A . 0.9700 no
  C20 H19B . 0.9700 no
  C21 C22 . 1.536(3) no
  C21 H18 . 0.9800 no
  C22 C23 . 1.528(3) no
  C22 H24A . 0.9700 no
  C22 H24B . 0.9700 no
  C23 C24 . 1.532(3) no
  C23 C25 . 1.539(3) no
  C23 H26 . 0.9800 no
  C24 H25A . 0.9700 no
  C24 H25B . 0.9700 no
  C25 H23A . 0.9700 no
  C25 H23B . 0.9700 no