#------------------------------------------------------------------------------
#$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012786.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_2012786
_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
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
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  'C20 H16 F5 N O3'
_chemical_formula_weight  413.34
_symmetry_cell_setting  Monoclinic
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y-1/2, z-1/2'
_cell_length_a  9.5390(10)
_cell_length_b  16.7160(10)
_cell_length_c  11.7200(10)
_cell_angle_alpha  90
_cell_angle_beta  92.900(10)
_cell_angle_gamma  90
_cell_volume  1866.6(3)
_cell_formula_units_Z  4
_cell_measurement_temperature  90(2)
_exptl_crystal_density_diffrn  1.471
_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 0.1019(3) 1.11780(13) 0.76904(17) 0.0865(8) Uani d . 1 . . F
  F2 0.0741(2) 1.09325(14) 0.94562(17) 0.0794(7) Uani d . 1 . . F
  F3 0.4088(3) 1.11339(19) 0.9155(3) 0.1466(15) Uani d . 1 . . F
  F4 0.2623(3) 1.19415(19) 0.9822(3) 0.1334(12) Uani d . 1 . . F
  F5 0.3052(4) 1.1986(2) 0.8093(3) 0.1545(14) Uani d . 1 . . F
  O1 0.2639(4) 1.0424(2) 1.1005(2) 0.1088(12) Uani d . 1 . . O
  O2 0.2524(3) 0.9091(2) 1.1214(2) 0.0840(9) Uani d . 1 . . O
  O3 0.2561(4) 0.7769(2) 1.0951(3) 0.1043(11) Uani d . 1 . . O
  C1 0.2339(3) 0.9997(2) 0.6232(2) 0.0489(9) Uani d . 1 . . C
  C2 0.3333(4) 1.0571(2) 0.5971(3) 0.0630(10) Uani d . 1 . . C
  H2 0.3789 1.0873 0.6544 0.076 Uiso calc R 1 . . H
  C3 0.3620(4) 1.0677(3) 0.4850(3) 0.0775(12) Uani d . 1 . . C
  H3 0.4280 1.1058 0.4661 0.093 Uiso calc R 1 . . H
  C4 0.2938(5) 1.0220(3) 0.3972(3) 0.0763(13) Uani d . 1 . . C
  H4 0.3139 1.0317 0.3217 0.092 Uiso calc R 1 . . H
  C5 0.2010(4) 0.9653(2) 0.4206(3) 0.0635(10) Uani d . 1 . . C
  H5 0.1573 0.9348 0.3628 0.076 Uiso calc R 1 . . H
  C6 0.1718(4) 0.9533(2) 0.5346(3) 0.0509(9) Uani d . 1 . . C
  C7 -0.0035(4) 0.8401(2) 0.5183(3) 0.0738(12) Uani d . 1 . . C
  H7A -0.0473 0.8049 0.5706 0.111 Uiso calc R 1 . . H
  H7B 0.0535 0.8094 0.4692 0.111 Uiso calc R 1 . . H
  H7C -0.0744 0.8681 0.4731 0.111 Uiso calc R 1 . . H
  C8 0.0894(4) 0.9077(2) 0.6987(3) 0.0518(9) Uani d . 1 . . C
  C9 0.0031(4) 0.8562(2) 0.7711(3) 0.0703(11) Uani d . 1 . . C
  H9A -0.0913 0.8539 0.7388 0.105 Uiso calc R 1 . . H
  H9B 0.0028 0.8783 0.8468 0.105 Uiso calc R 1 . . H
  H9C 0.0422 0.8033 0.7747 0.105 Uiso calc R 1 . . H
  C10 0.1797(3) 0.9700(2) 0.7281(2) 0.0499(9) Uani d . 1 . . C
  C11 0.2103(3) 1.0002(2) 0.8444(2) 0.0510(9) Uani d . 1 . . C
  C12 0.2562(3) 0.9532(2) 0.9333(3) 0.0548(10) Uani d . 1 . . C
  C13 0.2572(4) 0.9783(3) 1.0569(3) 0.0757(12) Uani d . 1 . . C
  C14 0.2646(4) 0.8416(3) 1.0536(3) 0.0733(12) Uani d . 1 . . C
  C15 0.2935(4) 0.8683(2) 0.9362(3) 0.0571(10) Uani d . 1 . . C
  C16 0.3695(4) 0.8242(2) 0.8651(3) 0.0604(10) Uani d . 1 . . C
  C17 0.4348(4) 0.8593(2) 0.7641(3) 0.0705(11) Uani d . 1 . . C
  H19A 0.3786 0.8465 0.6963 0.106 Uiso calc R 1 . . H
  H19B 0.5274 0.8377 0.7582 0.106 Uiso calc R 1 . . H
  H19C 0.4405 0.9163 0.7726 0.106 Uiso calc R 1 . . H
  C18 0.4007(5) 0.7371(2) 0.8843(4) 0.0944(14) Uani d . 1 . . C
  H20A 0.3570 0.7193 0.9519 0.142 Uiso calc R 1 . . H
  H20B 0.5003 0.7294 0.8937 0.142 Uiso calc R 1 . . H
  H20C 0.3646 0.7067 0.8198 0.142 Uiso calc R 1 . . H
  C19 0.1698(4) 1.0877(2) 0.8638(3) 0.0626(10) Uani d . 1 . . C
  C20 0.2892(6) 1.1463(3) 0.8951(4) 0.0893(14) Uani d . 1 . . C
  N1 0.0841(3) 0.89758(17) 0.5823(2) 0.0568(8) 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 0.120(2) 0.0799(16) 0.0573(13) 0.0276(14) -0.0156(12) -0.0024(11)
  F2 0.0753(15) 0.1020(18) 0.0614(13) 0.0155(13) 0.0102(11) -0.0204(12)
  F3 0.0700(19) 0.122(3) 0.244(4) -0.0082(18) -0.028(2) -0.061(3)
  F4 0.149(3) 0.121(2) 0.130(2) -0.015(2) 0.001(2) -0.068(2)
  F5 0.186(4) 0.130(3) 0.150(3) -0.051(3) 0.032(3) 0.004(2)
  O1 0.155(3) 0.118(3) 0.0509(17) 0.026(2) -0.0202(18) -0.0313(18)
  O2 0.091(2) 0.121(3) 0.0397(14) 0.0076(19) -0.0005(13) 0.0052(18)
  O3 0.124(3) 0.110(3) 0.077(2) -0.021(2) -0.0134(18) 0.038(2)
  C1 0.051(2) 0.056(2) 0.0388(19) 0.0042(18) -0.0032(15) 0.0016(16)
  C2 0.072(3) 0.074(3) 0.042(2) -0.002(2) 0.0004(18) 0.0015(18)
  C3 0.081(3) 0.095(3) 0.058(3) -0.010(2) 0.010(2) 0.007(2)
  C4 0.086(3) 0.105(4) 0.038(2) 0.005(3) 0.004(2) 0.003(2)
  C5 0.072(3) 0.079(3) 0.039(2) 0.009(2) -0.0045(17) -0.0108(19)
  C6 0.060(2) 0.058(2) 0.0331(18) 0.0114(19) -0.0077(16) -0.0043(17)
  C7 0.078(3) 0.079(3) 0.062(2) 0.001(2) -0.0227(19) -0.022(2)
  C8 0.055(2) 0.062(2) 0.0380(19) 0.0066(19) -0.0042(15) -0.0041(17)
  C9 0.069(3) 0.082(3) 0.060(2) -0.006(2) -0.0005(19) 0.001(2)
  C10 0.057(2) 0.061(2) 0.0310(17) 0.0039(18) -0.0033(15) -0.0033(16)
  C11 0.053(2) 0.063(2) 0.0367(19) 0.0021(18) -0.0033(15) -0.0070(17)
  C12 0.054(2) 0.075(3) 0.0346(18) -0.0017(19) -0.0046(15) -0.0065(18)
  C13 0.082(3) 0.105(4) 0.040(2) 0.017(3) -0.0110(19) -0.003(3)
  C14 0.068(3) 0.091(3) 0.059(3) -0.009(2) -0.014(2) 0.018(3)
  C15 0.058(2) 0.074(3) 0.0386(19) -0.004(2) -0.0095(16) 0.0022(19)
  C16 0.064(2) 0.063(3) 0.052(2) -0.005(2) -0.0160(19) 0.001(2)
  C17 0.069(3) 0.083(3) 0.060(2) 0.013(2) 0.0037(19) -0.009(2)
  C18 0.119(4) 0.075(3) 0.087(3) 0.013(3) -0.015(3) 0.004(3)
  C19 0.068(2) 0.078(3) 0.0407(19) 0.005(2) -0.0029(18) -0.0088(19)
  C20 0.102(4) 0.090(4) 0.076(3) -0.020(3) 0.006(3) -0.024(3)
  N1 0.0604(19) 0.064(2) 0.0447(16) 0.0021(16) -0.0103(14) -0.0104(15)
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 . 1.354(4) no
  F2 C19 . 1.360(4) no
  F3 C20 . 1.278(6) no
  F4 C20 . 1.333(5) no
  F5 C20 . 1.348(5) no
  O1 C13 . 1.188(5) no
  O2 C13 . 1.384(5) no
  O2 C14 . 1.388(5) no
  O3 C14 . 1.190(4) no
  C1 C2 . 1.393(5) no
  C1 C6 . 1.403(4) no
  C1 C10 . 1.446(4) no
  C2 C3 . 1.367(5) no
  C2 H2 . 0.9300 no
  C3 C4 . 1.413(5) no
  C3 H3 . 0.9300 no
  C4 C5 . 1.336(5) no
  C4 H4 . 0.9300 no
  C5 C6 . 1.393(5) no
  C5 H5 . 0.9300 no
  C6 N1 . 1.387(4) no
  C7 N1 . 1.456(4) no
  C7 H7A . 0.9600 no
  C7 H7B . 0.9600 no
  C7 H7C . 0.9600 no
  C8 N1 . 1.373(4) no
  C8 C10 . 1.384(5) no
  C8 C9 . 1.486(5) no
  C9 H9A . 0.9600 no
  C9 H9B . 0.9600 no
  C9 H9C . 0.9600 no
  C10 C11 . 1.469(4) no
  C11 C12 . 1.359(4) no
  C11 C19 . 1.533(5) no
  C12 C15 . 1.463(5) no
  C12 C13 . 1.508(5) no
  C14 C15 . 1.485(5) no
  C15 C16 . 1.351(5) no
  C16 C17 . 1.486(5) no
  C16 C18 . 1.501(5) no
  C17 H19A . 0.9600 no
  C17 H19B . 0.9600 no
  C17 H19C . 0.9600 no
  C18 H20A . 0.9600 no
  C18 H20B . 0.9600 no
  C18 H20C . 0.9600 no
  C19 C20 . 1.532(6) no
_cod_database_code 2012786