#------------------------------------------------------------------------------
#$Date: 2011-09-28 15:24:46 +0100 (Wed, 28 Sep 2011) $
#$Revision: 26848 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/21/2202142.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_2202142
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o153
_journal_page_last  o154
_publ_section_title
;
7-Ethylamino-4-(trifluoromethyl)coumarin
;
loop_
_publ_author_name
  'Jerry P. Jasinski'
  'John M. Jasinski'
  'Yu Li'
  'Daniel J. Crosby'
_chemical_name_common  'Coumarin 500'
_chemical_formula_moiety  'C12 H10 F3 N O2'
_chemical_formula_sum  'C12 H10 F3 N O2'
_chemical_formula_iupac  'C12 H10 F3 N O2'
_chemical_formula_weight  257.21
_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  10.567(6)
_cell_length_b  11.856(2)
_cell_length_c  4.6321(11)
_cell_angle_alpha  93.303(18)
_cell_angle_beta  100.25(3)
_cell_angle_gamma  99.14(3)
_cell_volume  561.6(4)
_cell_formula_units_Z  2
_cell_measurement_temperature  296(2)
_exptl_crystal_density_diffrn  1.521
_diffrn_ambient_temperature  296(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 0.9049(2) 1.03223(18) 1.2323(5) 0.0730(7) Uani d . 1 A . F
  F2 0.8126(2) 1.01490(17) 0.7811(4) 0.0735(7) Uani d . 1 A . F
  F3 0.7054(2) 1.05216(17) 1.1149(5) 0.0733(7) Uani d . 1 A . F
  O1 0.6623(2) 0.63630(18) 1.1197(5) 0.0518(6) Uani d . 1 . . O
  O11 0.8178(2) 0.6369(2) 1.5052(5) 0.0676(8) Uani d . 1 . . O
  N13 0.3057(3) 0.6034(3) 0.3366(6) 0.0619(9) Uani d . 1 . . N
  H13 0.2854 0.5250 0.3826 0.074 Uiso d R 1 A . H
  C2 0.7702(3) 0.6919(3) 1.3156(8) 0.0506(9) Uani d . 1 . . C
  C3 0.8152(3) 0.8090(3) 1.2752(7) 0.0501(9) Uani d . 1 . . C
  H3A 0.8917 0.8481 1.3942 0.060 Uiso d R 1 . . H
  C4 0.7484(3) 0.8644(3) 1.0654(7) 0.0443(8) Uani d . 1 A . C
  C5 0.5556(4) 0.8521(3) 0.6407(7) 0.0522(9) Uani d . 1 A . C
  H5A 0.5777 0.9288 0.6077 0.063 Uiso d R 1 . . H
  C6 0.4490(3) 0.7871(3) 0.4675(7) 0.0512(9) Uani d . 1 . . C
  H6A 0.3998 0.8202 0.3192 0.061 Uiso d R 1 A . H
  C7 0.4106(3) 0.6711(3) 0.5058(7) 0.0461(9) Uani d . 1 A . C
  C8 0.4869(3) 0.6239(3) 0.7312(7) 0.0488(9) Uani d . 1 . . C
  H8A 0.4645 0.5473 0.7645 0.059 Uiso d R 1 A . H
  C9 0.5939(3) 0.6909(3) 0.9018(7) 0.0424(8) Uani d . 1 A . C
  C10 0.6337(3) 0.8064(3) 0.8684(7) 0.0406(8) Uani d . 1 . . C
  C12 0.7930(4) 0.9901(3) 1.0496(8) 0.0548(10) Uani d . 1 . . C
  C14A 0.2146(7) 0.6327(6) 0.0982(17) 0.050(2) Uani d PD 0.725(8) A 1 C
  H14A 0.1765 0.5645 -0.0336 0.060 Uiso calc PR 0.725(8) A 1 H
  H14B 0.2601 0.6876 -0.0118 0.060 Uiso calc PR 0.725(8) A 1 H
  C15A 0.1072(7) 0.6833(7) 0.2058(16) 0.091(3) Uani d PD 0.725(8) A 1 C
  H15A 0.0510 0.7065 0.0416 0.137 Uiso calc PR 0.725(8) A 1 H
  H15B 0.1449 0.7487 0.3435 0.137 Uiso calc PR 0.725(8) A 1 H
  H15C 0.0574 0.6269 0.3008 0.137 Uiso calc PR 0.725(8) A 1 H
  C14B 0.206(2) 0.6776(14) 0.149(6) 0.071(8) Uani d PD 0.275(8) A 2 C
  H14C 0.1858 0.7388 0.2730 0.086 Uiso calc PR 0.275(8) A 2 H
  H14D 0.2396 0.7092 -0.0157 0.086 Uiso calc PR 0.275(8) A 2 H
  C15B 0.0882(15) 0.5834(16) 0.048(4) 0.093(7) Uani d PD 0.275(8) A 2 C
  H15D 0.0313 0.6063 -0.1150 0.140 Uiso calc PR 0.275(8) A 2 H
  H15E 0.0422 0.5700 0.2074 0.140 Uiso calc PR 0.275(8) A 2 H
  H15F 0.1169 0.5143 -0.0112 0.140 Uiso calc PR 0.275(8) A 2 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
  F1 0.0799(16) 0.0610(13) 0.0660(14) -0.0076(11) -0.0007(12) 0.0059(11)
  F2 0.1062(18) 0.0621(14) 0.0498(13) -0.0040(12) 0.0229(12) 0.0100(10)
  F3 0.0953(17) 0.0525(13) 0.0788(15) 0.0264(12) 0.0225(13) 0.0048(11)
  O1 0.0550(15) 0.0466(14) 0.0512(14) 0.0084(12) 0.0011(12) 0.0121(12)
  O11 0.0688(18) 0.0682(17) 0.0622(17) 0.0166(14) -0.0080(13) 0.0259(14)
  N13 0.062(2) 0.060(2) 0.057(2) 0.0054(17) -0.0039(17) 0.0165(16)
  C2 0.050(2) 0.049(2) 0.054(2) 0.0126(18) 0.0107(19) 0.0074(18)
  C3 0.050(2) 0.050(2) 0.047(2) 0.0049(17) 0.0045(17) 0.0013(16)
  C4 0.052(2) 0.043(2) 0.0411(19) 0.0112(17) 0.0165(17) 0.0040(16)
  C5 0.065(2) 0.045(2) 0.052(2) 0.0170(19) 0.0175(19) 0.0132(17)
  C6 0.051(2) 0.057(2) 0.048(2) 0.0171(19) 0.0043(18) 0.0178(18)
  C7 0.045(2) 0.048(2) 0.045(2) 0.0052(17) 0.0092(17) 0.0089(16)
  C8 0.055(2) 0.045(2) 0.048(2) 0.0106(18) 0.0091(18) 0.0139(17)
  C9 0.044(2) 0.050(2) 0.0366(19) 0.0158(17) 0.0077(16) 0.0102(16)
  C10 0.048(2) 0.0369(19) 0.0409(19) 0.0099(16) 0.0135(17) 0.0108(15)
  C12 0.062(3) 0.053(2) 0.047(2) 0.004(2) 0.010(2) -0.0004(18)
  C14A 0.049(4) 0.042(4) 0.059(4) 0.008(3) 0.009(3) 0.011(3)
  C15A 0.059(5) 0.116(7) 0.105(6) 0.030(5) 0.016(4) 0.014(5)
  C14B 0.072(15) 0.031(11) 0.096(16) 0.013(10) -0.025(12) 0.000(10)
  C15B 0.052(11) 0.105(15) 0.105(15) -0.010(10) -0.019(9) 0.028(12)
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 C12 . 1.331(4) ?
  F2 C12 . 1.338(4) ?
  F3 C12 . 1.334(4) ?
  O1 C2 . 1.372(4) ?
  O1 C9 . 1.387(4) ?
  O11 C2 . 1.209(4) ?
  N13 C7 . 1.350(4) ?
  N13 C14A . 1.427(8) ?
  N13 C14B . 1.64(2) ?
  N13 H13 . 0.9650 ?
  C2 C3 . 1.429(5) ?
  C3 C4 . 1.360(4) ?
  C3 H3A . 0.9301 ?
  C4 C10 . 1.430(4) ?
  C4 C12 . 1.500(5) ?
  C5 C6 . 1.356(5) ?
  C5 C10 . 1.409(4) ?
  C5 H5A . 0.9306 ?
  C6 C7 . 1.402(5) ?
  C6 H6A . 0.9300 ?
  C7 C8 . 1.401(4) ?
  C8 C9 . 1.363(4) ?
  C8 H8A . 0.9303 ?
  C9 C10 . 1.392(4) ?
  C14A C15A . 1.510(8) ?
  C14A H14A . 0.9700 ?
  C14A H14B . 0.9700 ?
  C15A H15A . 0.9600 ?
  C15A H15B . 0.9600 ?
  C15A H15C . 0.9600 ?
  C14B C15B . 1.515(17) ?
  C14B H14C . 0.9700 ?
  C14B H14D . 0.9700 ?
  C15B H15D . 0.9600 ?
  C15B H15E . 0.9600 ?
  C15B H15F . 0.9600 ?
_cod_database_code 2202142