data_2012785
_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  'C19 H16 F3 N O3'
_chemical_formula_weight  363.33
_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  11.6600(10)
_cell_length_b  17.164(2)
_cell_length_c  17.102(2)
_cell_angle_alpha  90
_cell_angle_beta  92.75(2)
_cell_angle_gamma  90
_cell_volume  3418.9(6)
_cell_formula_units_Z  8
_cell_measurement_temperature  90(2)
_exptl_crystal_density_diffrn  1.412
_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 0.22613(19) 1.09785(11) 0.43470(14) 0.0904(7) Uani d . 1 . . F
  F2 0.0949(2) 1.10349(12) 0.34558(14) 0.0960(7) Uani d . 1 . . F
  F3 0.0573(2) 1.06714(13) 0.46133(14) 0.1015(8) Uani d . 1 . . F
  F4 0.2333(2) 1.12479(12) 0.94786(14) 0.0924(7) Uani d . 1 . . F
  F5 0.1038(2) 1.14106(11) 0.85706(13) 0.0938(7) Uani d . 1 . . F
  F6 0.05982(19) 1.10020(12) 0.97093(12) 0.0841(7) Uani d . 1 . . F
  O1 -0.0978(3) 1.0120(3) 0.3540(2) 0.1347(15) Uani d . 1 . . O
  O2 -0.1001(2) 1.05884(18) 0.86356(16) 0.0973(9) Uani d . 1 . . O
  O3 -0.13110(19) 0.93079(19) 0.86106(14) 0.0787(8) Uani d . 1 . . O
  O4 -0.1153(2) 0.80151(19) 0.85582(17) 0.1003(10) Uani d . 1 . . O
  O5 -0.1091(3) 0.8839(3) 0.3340(2) 0.1192(13) Uani d . 1 . . O
  O6 -0.0736(3) 0.7585(2) 0.3072(2) 0.1595(18) Uani d . 1 . . O
  C1 0.3814(2) 0.98033(17) 0.38844(18) 0.0450(8) Uani d . 1 . . C
  C2 0.4146(3) 1.04229(19) 0.34213(19) 0.0565(9) Uani d . 1 . . C
  H2 0.3599 1.0740 0.3167 0.068 Uiso calc R 1 . . H
  C3 0.5292(3) 1.0558(2) 0.3346(2) 0.0738(11) Uani d . 1 . . C
  H3 0.5522 1.0979 0.3049 0.089 Uiso calc R 1 . . H
  C4 0.6120(3) 1.0077(3) 0.3707(2) 0.0779(11) Uani d . 1 . . C
  H4 0.6892 1.0185 0.3648 0.094 Uiso calc R 1 . . H
  C5 0.5824(3) 0.9452(2) 0.4143(2) 0.0679(10) Uani d . 1 . . C
  H5 0.6379 0.9127 0.4377 0.082 Uiso calc R 1 . . H
  C6 0.4666(3) 0.93187(19) 0.42256(18) 0.0514(8) Uani d . 1 . . C
  C7 0.4723(3) 0.8113(2) 0.5064(2) 0.0838(12) Uani d . 1 . . C
  H7A 0.4983 0.7724 0.4710 0.126 Uiso calc R 1 . . H
  H7B 0.4211 0.7879 0.5419 0.126 Uiso calc R 1 . . H
  H7C 0.5371 0.8331 0.5354 0.126 Uiso calc R 1 . . H
  C8 0.2951(3) 0.88273(18) 0.45241(18) 0.0516(8) Uani d . 1 . . C
  C9 0.2144(3) 0.8295(2) 0.4912(2) 0.0752(11) Uani d . 1 . . C
  H9A 0.1389 0.8521 0.4890 0.113 Uiso calc R 1 . . H
  H9B 0.2400 0.8220 0.5448 0.113 Uiso calc R 1 . . H
  H9C 0.2121 0.7802 0.4646 0.113 Uiso calc R 1 . . H
  C10 0.2727(2) 0.94845(17) 0.40768(17) 0.0455(8) Uani d . 1 . . C
  C11 0.1586(3) 0.97712(18) 0.38420(18) 0.0503(8) Uani d . 1 . . C
  C12 0.0760(3) 0.9320(2) 0.3490(2) 0.0589(9) Uani d . 1 . . C
  C13 -0.0489(4) 0.9515(3) 0.3463(3) 0.0898(14) Uani d . 1 . . C
  C14 -0.0360(5) 0.8222(4) 0.3193(3) 0.1089(18) Uani d . 1 . . C
  C15 0.0827(3) 0.8532(2) 0.3167(2) 0.0716(11) Uani d . 1 . . C
  C16 0.1642(4) 0.8194(2) 0.2740(2) 0.0768(12) Uani d . 1 . . C
  C17 0.2717(3) 0.8586(2) 0.2544(2) 0.0763(11) Uani d . 1 . . C
  H17A 0.2609 0.9140 0.2558 0.114 Uiso calc R 1 . . H
  H17B 0.2922 0.8432 0.2030 0.114 Uiso calc R 1 . . H
  H17C 0.3320 0.8442 0.2918 0.114 Uiso calc R 1 . . H
  C18 0.1493(5) 0.7382(2) 0.2398(3) 0.129(2) Uani d . 1 . . C
  H18A 0.1028 0.7075 0.2729 0.193 Uiso calc R 1 . . H
  H18B 0.2232 0.7141 0.2364 0.193 Uiso calc R 1 . . H
  H18C 0.1126 0.7417 0.1884 0.193 Uiso calc R 1 . . H
  C19 0.1329(3) 1.0612(2) 0.4066(2) 0.0639(10) Uani d . 1 . . C
  C20 0.2987(3) 0.90792(17) 0.94785(17) 0.0469(8) Uani d . 1 . . C
  C21 0.2374(3) 0.85341(18) 0.98906(18) 0.0557(9) Uani d . 1 . . C
  H24 0.1583 0.8581 0.9921 0.067 Uiso calc R 1 . . H
  C22 0.2952(3) 0.7924(2) 1.0253(2) 0.0735(11) Uani d . 1 . . C
  H23 0.2545 0.7552 1.0522 0.088 Uiso calc R 1 . . H
  C23 0.4140(4) 0.7856(2) 1.0222(2) 0.0781(11) Uani d . 1 . . C
  H22 0.4509 0.7439 1.0474 0.094 Uiso calc R 1 . . H
  C24 0.4770(3) 0.8380(2) 0.9837(2) 0.0669(10) Uani d . 1 . . C
  H21 0.5564 0.8334 0.9825 0.080 Uiso calc R 1 . . H
  C25 0.4184(3) 0.89923(19) 0.94566(18) 0.0508(8) Uani d . 1 . . C
  C26 0.5810(3) 0.9712(2) 0.8870(2) 0.0758(11) Uani d . 1 . . C
  H28A 0.6000 0.9385 0.8440 0.114 Uiso calc R 1 . . H
  H28B 0.6278 0.9573 0.9326 0.114 Uiso calc R 1 . . H
  H28C 0.5946 1.0247 0.8739 0.114 Uiso calc R 1 . . H
  C27 0.3709(3) 1.00808(18) 0.87842(18) 0.0526(8) Uani d . 1 . . C
  C28 0.3908(3) 1.0760(2) 0.8268(2) 0.0727(11) Uani d . 1 . . C
  H27A 0.4266 1.1172 0.8571 0.109 Uiso calc R 1 . . H
  H27B 0.3187 1.0939 0.8041 0.109 Uiso calc R 1 . . H
  H27C 0.4398 1.0608 0.7860 0.109 Uiso calc R 1 . . H
  C29 0.2697(3) 0.97747(16) 0.90483(17) 0.0464(8) Uani d . 1 . . C
  C30 0.1540(3) 1.00961(18) 0.88983(18) 0.0499(8) Uani d . 1 . . C
  C31 0.0610(3) 0.96745(18) 0.86320(17) 0.0502(8) Uani d . 1 . . C
  C32 -0.0601(3) 0.9951(3) 0.8630(2) 0.0669(10) Uani d . 1 . . C
  C33 -0.0672(3) 0.8631(3) 0.8529(2) 0.0682(10) Uani d . 1 . . C
  C34 0.0518(3) 0.88525(19) 0.83957(18) 0.0513(8) Uani d . 1 . . C
  C35 0.1218(3) 0.84008(19) 0.79878(19) 0.0578(9) Uani d . 1 . . C
  C36 0.2275(3) 0.8695(2) 0.76425(19) 0.0654(10) Uani d . 1 . . C
  H34A 0.2247 0.9253 0.7615 0.098 Uiso calc R 1 . . H
  H34B 0.2330 0.8485 0.7125 0.098 Uiso calc R 1 . . H
  H34C 0.2933 0.8537 0.7963 0.098 Uiso calc R 1 . . H
  C37 0.0954(4) 0.7560(2) 0.7798(3) 0.0998(14) Uani d . 1 . . C
  H35A 0.0347 0.7382 0.8113 0.150 Uiso calc R 1 . . H
  H35B 0.1628 0.7250 0.7906 0.150 Uiso calc R 1 . . H
  H35C 0.0719 0.7514 0.7255 0.150 Uiso calc R 1 . . H
  C38 0.1379(3) 1.0939(2) 0.9157(2) 0.0659(10) Uani d . 1 . . C
  N1 0.4118(2) 0.87325(15) 0.46166(16) 0.0567(7) Uani d . 1 . . N
  N2 0.4605(2) 0.96075(16) 0.90300(15) 0.0555(7) 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 0.0758(15) 0.0578(13) 0.136(2) 0.0155(11) -0.0108(14) -0.0230(12)
  F2 0.1108(18) 0.0761(15) 0.0998(17) 0.0305(13) -0.0076(14) 0.0283(13)
  F3 0.1003(18) 0.0990(18) 0.1089(18) 0.0332(14) 0.0424(15) 0.0058(14)
  F4 0.0962(17) 0.0581(13) 0.120(2) 0.0052(12) -0.0189(14) -0.0310(12)
  F5 0.138(2) 0.0572(13) 0.0843(16) 0.0290(13) -0.0105(14) 0.0141(12)
  F6 0.0951(16) 0.0847(15) 0.0721(14) 0.0306(12) -0.0013(13) -0.0186(11)
  O1 0.0510(19) 0.166(4) 0.186(4) 0.025(2) -0.009(2) 0.039(3)
  O2 0.0806(19) 0.110(2) 0.099(2) 0.0499(18) -0.0162(16) -0.0040(17)
  O3 0.0427(14) 0.117(2) 0.0751(18) 0.0028(16) -0.0063(12) 0.0012(15)
  O4 0.0766(19) 0.111(2) 0.112(2) -0.0411(18) -0.0047(17) 0.0013(18)
  O5 0.062(2) 0.176(4) 0.117(3) -0.049(2) -0.0237(18) 0.041(3)
  O6 0.166(3) 0.158(3) 0.149(3) -0.119(3) -0.052(3) 0.043(3)
  C1 0.0416(19) 0.0429(19) 0.0499(19) 0.0039(15) -0.0059(15) -0.0077(15)
  C2 0.044(2) 0.058(2) 0.067(2) -0.0031(16) -0.0006(17) -0.0023(18)
  C3 0.064(3) 0.076(3) 0.083(3) -0.014(2) 0.013(2) -0.007(2)
  C4 0.045(2) 0.103(3) 0.085(3) -0.008(2) -0.001(2) -0.022(3)
  C5 0.051(2) 0.082(3) 0.070(3) 0.016(2) -0.0115(19) -0.019(2)
  C6 0.042(2) 0.057(2) 0.054(2) 0.0092(17) -0.0093(16) -0.0132(17)
  C7 0.098(3) 0.066(3) 0.084(3) 0.032(2) -0.032(2) 0.000(2)
  C8 0.054(2) 0.047(2) 0.053(2) 0.0023(16) -0.0082(16) -0.0019(16)
  C9 0.082(3) 0.068(2) 0.074(3) -0.009(2) -0.007(2) 0.0196(19)
  C10 0.0393(18) 0.0438(19) 0.052(2) -0.0015(14) -0.0086(15) -0.0007(15)
  C11 0.0396(19) 0.056(2) 0.055(2) 0.0030(16) -0.0025(16) 0.0100(16)
  C12 0.039(2) 0.072(3) 0.065(2) -0.0050(17) -0.0090(17) 0.0223(19)
  C13 0.052(3) 0.122(4) 0.093(3) -0.010(3) -0.011(2) 0.039(3)
  C14 0.107(4) 0.127(5) 0.089(4) -0.067(4) -0.037(3) 0.044(3)
  C15 0.071(3) 0.073(3) 0.068(3) -0.028(2) -0.029(2) 0.020(2)
  C16 0.098(3) 0.053(2) 0.075(3) -0.012(2) -0.040(3) 0.004(2)
  C17 0.076(3) 0.079(3) 0.072(3) 0.011(2) -0.022(2) -0.020(2)
  C18 0.179(5) 0.072(3) 0.130(4) -0.012(3) -0.061(4) -0.022(3)
  C19 0.049(2) 0.068(3) 0.075(3) 0.0167(19) 0.004(2) 0.008(2)
  C20 0.052(2) 0.0437(19) 0.0443(19) 0.0009(15) -0.0061(16) -0.0031(15)
  C21 0.053(2) 0.057(2) 0.057(2) 0.0021(17) -0.0065(17) 0.0010(17)
  C22 0.080(3) 0.059(2) 0.080(3) 0.000(2) -0.005(2) 0.013(2)
  C23 0.084(3) 0.063(3) 0.085(3) 0.016(2) -0.019(2) 0.011(2)
  C24 0.051(2) 0.072(3) 0.076(3) 0.015(2) -0.018(2) -0.008(2)
  C25 0.046(2) 0.053(2) 0.053(2) 0.0071(16) -0.0083(16) -0.0092(17)
  C26 0.049(2) 0.101(3) 0.076(3) -0.012(2) 0.0008(19) -0.017(2)
  C27 0.054(2) 0.050(2) 0.052(2) -0.0038(17) -0.0055(17) -0.0072(16)
  C28 0.086(3) 0.064(2) 0.068(3) -0.017(2) 0.001(2) -0.0008(19)
  C29 0.050(2) 0.0418(19) 0.0469(19) -0.0003(15) -0.0073(16) -0.0039(14)
  C30 0.053(2) 0.047(2) 0.049(2) 0.0097(16) -0.0033(16) 0.0016(15)
  C31 0.047(2) 0.059(2) 0.0438(19) 0.0133(17) -0.0054(16) 0.0071(16)
  C32 0.060(3) 0.089(3) 0.051(2) 0.020(2) -0.0099(18) 0.003(2)
  C33 0.058(2) 0.087(3) 0.059(2) -0.010(2) -0.0066(19) 0.000(2)
  C34 0.047(2) 0.056(2) 0.050(2) -0.0032(16) -0.0110(16) -0.0004(16)
  C35 0.057(2) 0.055(2) 0.059(2) 0.0012(17) -0.0165(19) -0.0032(17)
  C36 0.064(2) 0.074(2) 0.058(2) 0.0101(19) 0.0030(18) -0.0150(18)
  C37 0.108(3) 0.062(3) 0.128(4) -0.010(2) -0.006(3) -0.031(2)
  C38 0.073(3) 0.058(2) 0.066(3) 0.016(2) -0.007(2) -0.001(2)
  N1 0.0581(18) 0.0470(16) 0.0629(19) 0.0138(14) -0.0186(14) -0.0020(14)
  N2 0.0435(16) 0.0604(18) 0.0623(18) -0.0061(14) -0.0008(14) -0.0080(14)
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 C19 . 1.326(4) no
  F2 C19 . 1.331(4) no
  F3 C19 . 1.319(4) no
  F4 C38 . 1.327(4) no
  F5 C38 . 1.336(4) no
  F6 C38 . 1.347(4) no
  O1 C13 . 1.195(5) no
  O2 C32 . 1.190(4) no
  O3 C32 . 1.379(4) no
  O3 C33 . 1.391(4) no
  O4 C33 . 1.199(4) no
  O5 C13 . 1.366(5) no
  O5 C14 . 1.390(6) no
  O6 C14 . 1.193(5) no
  C1 C2 . 1.392(4) no
  C1 C6 . 1.401(4) no
  C1 C10 . 1.433(4) no
  C2 C3 . 1.368(4) no
  C2 H2 . 0.9300 no
  C3 C4 . 1.392(5) no
  C3 H3 . 0.9300 no
  C4 C5 . 1.360(5) no
  C4 H4 . 0.9300 no
  C5 C6 . 1.383(4) no
  C5 H5 . 0.9300 no
  C6 N1 . 1.382(4) no
  C7 N1 . 1.471(4) no
  C7 H7A . 0.9600 no
  C7 H7B . 0.9600 no
  C7 H7C . 0.9600 no
  C8 N1 . 1.372(4) no
  C8 C10 . 1.381(4) no
  C8 C9 . 1.490(4) no
  C9 H9A . 0.9600 no
  C9 H9B . 0.9600 no
  C9 H9C . 0.9600 no
  C10 C11 . 1.457(4) no
  C11 C12 . 1.354(4) no
  C11 C19 . 1.526(5) no
  C12 C15 . 1.465(5) no
  C12 C13 . 1.493(5) no
  C14 C15 . 1.484(6) no
  C15 C16 . 1.357(5) no
  C16 C17 . 1.476(5) no
  C16 C18 . 1.517(5) no
  C17 H17A . 0.9600 no
  C17 H17B . 0.9600 no
  C17 H17C . 0.9600 no
  C18 H18A . 0.9600 no
  C18 H18B . 0.9600 no
  C18 H18C . 0.9600 no
  C20 C21 . 1.390(4) no
  C20 C25 . 1.405(4) no
  C20 C29 . 1.434(4) no
  C21 C22 . 1.377(4) no
  C21 H24 . 0.9300 no
  C22 C23 . 1.393(5) no
  C22 H23 . 0.9300 no
  C23 C24 . 1.353(5) no
  C23 H22 . 0.9300 no
  C24 C25 . 1.398(4) no
  C24 H21 . 0.9300 no
  C25 N2 . 1.387(4) no
  C26 N2 . 1.455(4) no
  C26 H28A . 0.9600 no
  C26 H28B . 0.9600 no
  C26 H28C . 0.9600 no
  C27 N2 . 1.373(4) no
  C27 C29 . 1.387(4) no
  C27 C28 . 1.487(4) no
  C28 H27A . 0.9600 no
  C28 H27B . 0.9600 no
  C28 H27C . 0.9600 no
  C29 C30 . 1.469(4) no
  C30 C31 . 1.364(4) no
  C30 C38 . 1.526(5) no
  C31 C34 . 1.470(4) no
  C31 C32 . 1.489(5) no
  C33 C34 . 1.468(5) no
  C34 C35 . 1.345(4) no
  C35 C36 . 1.480(5) no
  C35 C37 . 1.507(5) no
  C36 H34A . 0.9600 no
  C36 H34B . 0.9600 no
  C36 H34C . 0.9600 no
  C37 H35A . 0.9600 no
  C37 H35B . 0.9600 no
  C37 H35C . 0.9600 no