data_2012789
_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  'C28 H24 F7 N O3'
_chemical_formula_weight  555.48
_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  10.3130(10)
_cell_length_b  10.9240(10)
_cell_length_c  11.7290(10)
_cell_angle_alpha  87.670(10)
_cell_angle_beta  82.650(10)
_cell_angle_gamma  73.240(10)
_cell_volume  1254.8(2)
_cell_formula_units_Z  2
_cell_measurement_temperature  90(2)
_exptl_crystal_density_diffrn  1.470
_diffrn_ambient_temperature  273(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 0.34257(12) 1.23487(11) 0.77112(11) 0.0299(3) Uani d . 1 . . F
  F2 0.22772(14) 1.21890(11) 0.63358(10) 0.0317(3) Uani d . 1 . . F
  F3 0.07838(12) 1.22282(12) 0.91734(11) 0.0300(3) Uani d . 1 . . F
  F4 -0.00043(12) 1.27194(12) 0.75383(12) 0.0355(3) Uani d . 1 . . F
  F5 0.17664(13) 1.42570(12) 0.90584(11) 0.0318(3) Uani d . 1 . . F
  F6 -0.03227(13) 1.47875(13) 0.87176(12) 0.0394(4) Uani d . 1 . . F
  F7 0.12849(15) 1.46782(12) 0.73239(12) 0.0401(4) Uani d . 1 . . F
  O1 0.33893(17) 1.16043(15) 0.98669(14) 0.0377(4) Uani d . 1 . . O
  O2 0.34123(16) 0.96665(15) 1.05525(13) 0.0330(4) Uani d . 1 . . O
  O3 0.34825(19) 0.76020(17) 1.08011(14) 0.0434(5) Uani d . 1 . . O
  C1 0.2327(2) 0.96503(19) 0.56842(18) 0.0206(5) Uani d . 1 . . C
  C2 0.3237(2) 0.9970(2) 0.48103(19) 0.0269(5) Uani d . 1 . . C
  H2 0.3804 1.0450 0.4969 0.032 Uiso calc R 1 . . H
  C3 0.3271(3) 0.9551(2) 0.3704(2) 0.0334(6) Uani d . 1 . . C
  H3 0.3882 0.9739 0.3118 0.040 Uiso calc R 1 . . H
  C4 0.2399(3) 0.8846(2) 0.34530(19) 0.0346(6) Uani d . 1 . . C
  H4 0.2431 0.8595 0.2699 0.042 Uiso calc R 1 . . H
  C5 0.1512(2) 0.8521(2) 0.4282(2) 0.0314(6) Uani d . 1 . . C
  H5 0.0935 0.8058 0.4108 0.038 Uiso calc R 1 . . H
  C6 0.1496(2) 0.89063(19) 0.54049(19) 0.0233(5) Uani d . 1 . . C
  C7 -0.0196(2) 0.7876(2) 0.6455(2) 0.0357(6) Uani d . 1 . . C
  H7A -0.0920 0.8292 0.6010 0.054 Uiso calc R 1 . . H
  H7B -0.0567 0.7801 0.7239 0.054 Uiso calc R 1 . . H
  H7C 0.0263 0.7040 0.6149 0.054 Uiso calc R 1 . . H
  C8 0.1124(2) 0.9158(2) 0.73193(19) 0.0227(5) Uani d . 1 . . C
  C9 0.0474(2) 0.9039(2) 0.85114(19) 0.0310(5) Uani d . 1 . . C
  H9A -0.0498 0.9261 0.8519 0.046 Uiso calc R 1 . . H
  H9B 0.0698 0.9605 0.9009 0.046 Uiso calc R 1 . . H
  H9C 0.0804 0.8174 0.8775 0.046 Uiso calc R 1 . . H
  C10 0.2076(2) 0.98050(19) 0.69132(18) 0.0199(5) Uani d . 1 . . C
  C11 0.2667(2) 1.04772(19) 0.76731(18) 0.0208(5) Uani d . 1 . . C
  C12 0.3296(2) 0.98912(19) 0.85813(18) 0.0205(5) Uani d . 1 . . C
  C13 0.3386(2) 1.0545(2) 0.96619(19) 0.0269(5) Uani d . 1 . . C
  C14 0.3538(2) 0.8441(2) 1.0130(2) 0.0300(5) Uani d . 1 . . C
  C15 0.3722(2) 0.8507(2) 0.88647(18) 0.0213(5) Uani d . 1 . . C
  C16 0.4449(2) 0.7498(2) 0.81970(18) 0.0200(5) Uani d . 1 . . C
  C17 0.4932(2) 0.7611(2) 0.69414(18) 0.0218(5) Uani d . 1 . . C
  H17 0.4614 0.8501 0.6685 0.026 Uiso calc R 1 . . H
  C18 0.4930(2) 0.6145(2) 0.86389(19) 0.0251(5) Uani d . 1 . . C
  H18 0.4598 0.6104 0.9456 0.030 Uiso calc R 1 . . H
  C19 0.6504(2) 0.5684(2) 0.84545(19) 0.0257(5) Uani d . 1 . . C
  H19A 0.6869 0.6217 0.8889 0.031 Uiso calc R 1 . . H
  H19B 0.6820 0.4811 0.8728 0.031 Uiso calc R 1 . . H
  C20 0.7011(2) 0.5752(2) 0.71720(19) 0.0277(5) Uani d . 1 . . C
  H20 0.8010 0.5464 0.7056 0.033 Uiso calc R 1 . . H
  C21 0.6508(2) 0.7143(2) 0.67766(19) 0.0273(5) Uani d . 1 . . C
  H21A 0.6841 0.7213 0.5972 0.033 Uiso calc R 1 . . H
  H21B 0.6864 0.7679 0.7217 0.033 Uiso calc R 1 . . H
  C22 0.4377(2) 0.6747(2) 0.6250(2) 0.0309(6) Uani d . 1 . . C
  H22A 0.3387 0.7028 0.6355 0.037 Uiso calc R 1 . . H
  H22B 0.4684 0.6807 0.5438 0.037 Uiso calc R 1 . . H
  C23 0.4884(2) 0.5360(2) 0.6659(2) 0.0336(6) Uani d . 1 . . C
  H23 0.4524 0.4812 0.6222 0.040 Uiso calc R 1 . . H
  C24 0.4363(2) 0.5300(2) 0.7934(2) 0.0333(6) Uani d . 1 . . C
  H24A 0.4647 0.4423 0.8204 0.040 Uiso calc R 1 . . H
  H24B 0.3374 0.5591 0.8040 0.040 Uiso calc R 1 . . H
  C25 0.6443(2) 0.4903(2) 0.6490(2) 0.0351(6) Uani d . 1 . . C
  H25A 0.6772 0.4937 0.5680 0.042 Uiso calc R 1 . . H
  H25B 0.6754 0.4024 0.6748 0.042 Uiso calc R 1 . . H
  C26 0.2392(2) 1.1913(2) 0.74699(18) 0.0224(5) Uani d . 1 . . C
  C27 0.1029(2) 1.2733(2) 0.81294(18) 0.0220(5) Uani d . 1 . . C
  C28 0.0946(2) 1.4139(2) 0.8314(2) 0.0272(5) Uani d . 1 . . C
  N1 0.07762(17) 0.86315(17) 0.64040(16) 0.0253(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 0.0225(7) 0.0240(7) 0.0445(8) -0.0097(5) 0.0004(6) -0.0057(6)
  F2 0.0494(9) 0.0204(7) 0.0228(7) -0.0074(6) -0.0019(6) 0.0028(5)
  F3 0.0280(7) 0.0278(7) 0.0305(7) -0.0046(6) 0.0018(6) 0.0033(6)
  F4 0.0267(7) 0.0339(8) 0.0463(9) -0.0025(6) -0.0167(6) -0.0099(6)
  F5 0.0325(7) 0.0276(7) 0.0367(8) -0.0066(6) -0.0113(6) -0.0076(6)
  F6 0.0310(8) 0.0307(8) 0.0494(9) 0.0070(6) -0.0110(6) -0.0132(7)
  F7 0.0621(10) 0.0204(7) 0.0348(8) -0.0067(7) -0.0086(7) 0.0047(6)
  O1 0.0453(11) 0.0253(10) 0.0426(10) -0.0036(8) -0.0174(8) -0.0113(8)
  O2 0.0410(10) 0.0279(9) 0.0236(9) 0.0029(7) -0.0086(7) -0.0048(7)
  O3 0.0631(13) 0.0335(10) 0.0235(9) -0.0018(9) 0.0019(8) 0.0057(8)
  C1 0.0208(11) 0.0156(11) 0.0222(11) 0.0016(9) -0.0072(9) 0.0025(9)
  C2 0.0297(13) 0.0198(12) 0.0256(12) 0.0022(10) -0.0047(10) 0.0020(9)
  C3 0.0423(15) 0.0254(13) 0.0232(12) 0.0022(11) 0.0016(10) 0.0020(10)
  C4 0.0569(17) 0.0236(13) 0.0179(12) 0.0004(12) -0.0117(11) -0.0015(10)
  C5 0.0388(14) 0.0210(12) 0.0333(14) -0.0008(10) -0.0175(11) -0.0016(10)
  C6 0.0230(12) 0.0154(11) 0.0282(12) 0.0041(9) -0.0128(9) -0.0022(9)
  C7 0.0287(14) 0.0278(13) 0.0556(17) -0.0102(11) -0.0184(12) -0.0013(12)
  C8 0.0202(11) 0.0173(11) 0.0294(12) -0.0007(9) -0.0092(9) 0.0000(9)
  C9 0.0254(13) 0.0347(14) 0.0326(13) -0.0102(11) -0.0004(10) 0.0035(11)
  C10 0.0186(11) 0.0155(11) 0.0240(11) -0.0013(9) -0.0053(9) 0.0005(9)
  C11 0.0174(11) 0.0185(11) 0.0247(12) -0.0032(9) -0.0006(9) -0.0015(9)
  C12 0.0185(11) 0.0178(11) 0.0232(11) -0.0019(9) -0.0024(9) -0.0016(9)
  C13 0.0211(12) 0.0279(14) 0.0274(12) 0.0028(10) -0.0092(9) -0.0042(10)
  C14 0.0318(13) 0.0280(13) 0.0246(12) 0.0011(10) -0.0042(10) -0.0023(11)
  C15 0.0206(11) 0.0215(12) 0.0219(11) -0.0055(9) -0.0057(9) 0.0033(9)
  C16 0.0177(11) 0.0198(11) 0.0237(11) -0.0053(9) -0.0079(9) 0.0026(9)
  C17 0.0239(12) 0.0146(11) 0.0244(12) 0.0000(9) -0.0069(9) 0.0013(9)
  C18 0.0287(12) 0.0188(11) 0.0270(12) -0.0043(9) -0.0072(10) 0.0034(9)
  C19 0.0282(12) 0.0189(11) 0.0287(12) -0.0009(9) -0.0127(10) 0.0029(9)
  C20 0.0223(12) 0.0224(12) 0.0328(13) 0.0026(9) -0.0048(10) 0.0019(10)
  C21 0.0267(12) 0.0261(12) 0.0257(12) -0.0029(10) -0.0027(10) 0.0041(10)
  C22 0.0356(14) 0.0234(12) 0.0302(13) 0.0029(10) -0.0167(11) -0.0031(10)
  C23 0.0394(14) 0.0198(12) 0.0433(15) -0.0031(10) -0.0231(12) -0.0037(11)
  C24 0.0294(13) 0.0186(12) 0.0523(16) -0.0049(10) -0.0119(11) 0.0032(11)
  C25 0.0446(15) 0.0221(13) 0.0312(14) 0.0056(11) -0.0110(11) -0.0029(10)
  C26 0.0264(12) 0.0199(11) 0.0215(11) -0.0069(9) -0.0045(9) -0.0002(9)
  C27 0.0218(11) 0.0211(12) 0.0235(11) -0.0048(9) -0.0091(9) 0.0024(9)
  C28 0.0265(12) 0.0225(12) 0.0290(13) 0.0008(10) -0.0077(10) -0.0018(10)
  N1 0.0232(10) 0.0213(10) 0.0337(11) -0.0074(8) -0.0105(8) 0.0040(8)
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 . 1.351(2) no
  F2 C26 . 1.364(2) no
  F3 C27 . 1.347(2) no
  F4 C27 . 1.347(2) no
  F5 C28 . 1.325(2) no
  F6 C28 . 1.331(3) no
  F7 C28 . 1.334(3) no
  O1 C13 . 1.193(3) no
  O2 C13 . 1.387(3) no
  O2 C14 . 1.411(3) no
  O3 C14 . 1.193(3) no
  C1 C2 . 1.403(3) no
  C1 C6 . 1.413(3) no
  C1 C10 . 1.440(3) no
  C2 C3 . 1.386(3) no
  C2 H2 . 0.9300 no
  C3 C4 . 1.405(3) no
  C3 H3 . 0.9300 no
  C4 C5 . 1.357(3) no
  C4 H4 . 0.9300 no
  C5 C6 . 1.396(3) no
  C5 H5 . 0.9300 no
  C6 N1 . 1.375(3) no
  C7 N1 . 1.466(3) no
  C7 H7A . 0.9600 no
  C7 H7B . 0.9600 no
  C7 H7C . 0.9600 no
  C8 N1 . 1.371(3) no
  C8 C10 . 1.395(3) no
  C8 C9 . 1.489(3) no
  C9 H9A . 0.9600 no
  C9 H9B . 0.9600 no
  C9 H9C . 0.9600 no
  C10 C11 . 1.468(3) no
  C11 C12 . 1.359(3) no
  C11 C26 . 1.526(3) no
  C12 C15 . 1.484(3) no
  C12 C13 . 1.506(3) no
  C14 C15 . 1.474(3) no
  C15 C16 . 1.355(3) no
  C16 C17 . 1.505(3) no
  C16 C18 . 1.510(3) no
  C17 C22 . 1.539(3) no
  C17 C21 . 1.546(3) no
  C17 H17 . 0.9800 no
  C18 C24 . 1.541(3) no
  C18 C19 . 1.544(3) no
  C18 H18 . 0.9800 no
  C19 C20 . 1.534(3) no
  C19 H19A . 0.9700 no
  C19 H19B . 0.9700 no
  C20 C25 . 1.529(3) no
  C20 C21 . 1.531(3) no
  C20 H20 . 0.9800 no
  C21 H21A . 0.9700 no
  C21 H21B . 0.9700 no
  C22 C23 . 1.533(3) no
  C22 H22A . 0.9700 no
  C22 H22B . 0.9700 no
  C23 C24 . 1.528(4) no
  C23 C25 . 1.529(3) no
  C23 H23 . 0.9800 no
  C24 H24A . 0.9700 no
  C24 H24B . 0.9700 no
  C25 H25A . 0.9700 no
  C25 H25B . 0.9700 no
  C26 C27 . 1.559(3) no
  C27 C28 . 1.536(3) no