#------------------------------------------------------------------------------
#$Date: 2016-02-19 15:29:56 +0100 (vie 19 de feb de 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/40/2004023.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2004023
loop_
_publ_author_name
'Abubakar, A. B.'
'Pritchard, R. G.'
'Suliman, N. N. E.'
'Tipping, A. E.'
_publ_section_title
;
 Ethyl 6,7-Bis(trifluoromethyl)isocoumarin-3-carboxylate: Formed by a
 Novel Diels--Alder Cycloaddition Involving Two Different
 α,β-Unsaturated Esters
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2100
_journal_page_last               2102
_journal_paper_doi               10.1107/S0108270195004781
_journal_volume                  51
_journal_year                    1995
_chemical_compound_source        'synthesized at UMIST'
_chemical_formula_moiety         'C14 H8 F6 O4'
_chemical_formula_structural     'C14 H8 F6 O4'
_chemical_formula_sum            'C14 H8 F6 O4'
_chemical_formula_weight         354.21
_chemical_melting_point          466.0(10)
_chemical_name_systematic
;
Ethyl-6,7-bis(trifluoromethyl)isocumarin-3-carboxylate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_cell_angle_alpha                90
_cell_angle_beta                 115.30(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.511(5)
_cell_length_b                   6.666(3)
_cell_length_c                   17.351(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      21.96
_cell_measurement_theta_min      12.60
_cell_volume                     2876.8(16)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction
'TEXSAN: PROCESS (Molecular Structure Corporation, 1985)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'TEXSAN: FINISH'
_computing_structure_refinement  'TEXSAN: LS'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      296
_diffrn_measurement_device       CAD4
_diffrn_measurement_method       'ω/2θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     .71069
_diffrn_reflns_av_R_equivalents  .032
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -030
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4626
_diffrn_reflns_theta_max         23.0
_diffrn_reflns_theta_min         1.0
_diffrn_standards_decay_%        'no significant trend'
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .1602
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_description       needle
_exptl_crystal_F_000             1424.0
_exptl_crystal_size_max          .40
_exptl_crystal_size_mid          .15
_exptl_crystal_size_min          .15
_refine_diff_density_max         .35
_refine_diff_density_min         -0.37
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.93
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         521
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          .068
_refine_ls_shift/esd_max         .09
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_obs         .042
_reflns_number_observed          521
_reflns_number_total             2002
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            li1134.cif
_cod_data_source_block           U169zzz
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '465-467K' was changed to '466.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2876(3)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2004023
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
1/2+x,1/2+y,z
1/2-x,1/2-y,-z
-x,y,1/2-z
x,-y,1/2+z
1/2-x,1/2+y,1/2-z
1/2+x,1/2-y,1/2+z
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
C12 0.16(3) 0.09(3) 0.14(3) 0.10(3) -0.05(2) -0.05(3)
F13A 0.17(2) 0.19(2) 0.080(10) 0.11(2) -0.070(10) -0.08(2)
F13B 0.080(10) 0.30(3) 0.100(10) -0.02(2) 0.010(10) -0.03(2)
F13C 0.18(2) 0.10(2) 0.17(2) 0.00(2) -0.020(10) 0.07(2)
F14A 0.080(10) 0.11(2) 0.25(2) 0.030(10) 0.09(2) 0.02(2)
F14B 0.14(2) 0.13(2) 0.25(2) 0.12(2) -0.05(2) -0.09(2)
F14C 0.15(2) 0.09(2) 0.23(2) 0.010(10) 0.11(2) 0.07(2)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
O1 .2786(5) .937(2) .7496(9) .077(6)
O2 .2983(5) .663(3) .7020(8) .061(5)
O9 .3183(6) .203(3) .6160(10) .105(7)
O10 .3588(5) .343(3) .7447(8) .073(5)
C1 .2648(10) .830(4) .690(2) .073(9)
C1a .2172(8) .834(4) .6100(10) .041(7)
C3 .2870(9) .516(4) .6420(10) .049(7)
C4 .2417(9) .520(4) .5700(10) .052(7)
C4a .2038(8) .680(4) .5500(10) .041(7)
C5 .1570(8) .698(4) .4750(10) .048(7)
C6 .1198(9) .851(4) .4640(10) .050(7)
C7 .1346(10) 1.003(4) .5260(10) .055(8)
C8 .1814(8) .988(4) .5980(10) .058(8)
C9 .3216(9) .322(5) .665(2) .073(9)
C11 .3956(9) .160(5) .7710(10) .087(10)
C12 .4320(10) .198(4) .854(2) .170(10)
C13 .0700(10) .835(7) .381(2) .090(10)
C14 .093(2) 1.163(7) .520(2) .100(10)
F13A .0688(7) .706(3) .3340(10) .190(10)
F13B .0299(6) .825(4) .3952(9) .170(10)
F13C .0605(8) .994(3) .3340(10) .180(10)
F14A .0503(6) 1.126(2) .5130(10) .140(10)
F14B .1160(7) 1.293(3) .5790(10) .220(10)
F14C .0860(7) 1.276(3) .4510(10) .140(10)
H4 .2345 .4131 .5311 .0620
H5 .1502 .6047 .4304 .0572
H8 .1898 1.0874 .6413 .0693
H11A .3757 .0423 .7690 .1041
H11B .4134 .1447 .7353 .1041
H12A .4569 .0900 .8739 .2002
H12B .4512 .3185 .8552 .2002
H12C .4138 .2129 .8889 .2002
loop_
_atom_type_symbol
_atom_type_scat_source
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
C 'International Tables' .002 .002
F 'International Tables' .014 .010
O 'International Tables' .008 .006
H 'International Tables' .000 .000
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
3 -1 -6
4 -1 3
0 0 8
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C1 O2 C3 122(2) yes
C9 O10 C11 110(2) ?
O1 C1 O2 114(2) yes
O1 C1 C1a 131(3) ?
O2 C1 C1a 115(3) yes
C1 C1a C4a 123(3) yes
C1 C1a C8 117(3) yes
C4a C1a C8 120(2) yes
O2 C3 C4 121(2) yes
O2 C3 C9 119(2) ?
C4 C3 C9 119(3) ?
C3 C4 C4a 123(2) yes
C1a C4a C4 116(2) yes
C1a C4a C5 118(2) yes
C4 C4a C5 126(3) yes
C4a C5 C6 121(2) yes
C5 C6 C7 118(2) yes
C5 C6 C13 113(3) ?
C7 C6 C13 129(3) ?
C6 C7 C8 120(3) yes
C6 C7 C14 119(3) ?
C8 C7 C14 120(3) ?
C1a C8 C7 122(3) yes
O9 C9 O10 129(3) ?
O9 C9 C3 123(3) ?
O10 C9 C3 107(3) ?
O10 C11 C12 105(2) ?
C6 C13 F13A 117(4) ?
C6 C13 F13B 110(3) ?
C6 C13 F13C 113(3) ?
F13A C13 F13B 110(4) ?
F13A C13 F13C 103(3) ?
F13B C13 F13C 102(4) ?
C7 C14 F14A 123(4) ?
C7 C14 F14B 109(3) ?
C7 C14 F14C 107(3) ?
F14A C14 F14B 110(4) ?
F14A C14 F14C 106(3) ?
F14B C14 F14C 100(4) ?
C3 C4 H4 118.69 ?
C4a C4 H4 118.71 ?
C4a C5 H5 119.29 ?
C6 C5 H5 119.34 ?
C1a C8 H8 119.07 ?
C7 C8 H8 119.13 ?
O10 C11 H11A 110.49 ?
O10 C11 H11B 110.44 ?
C12 C11 H11A 110.55 ?
C12 C11 H11B 110.48 ?
H11A C11 H11B 109.57 ?
C11 C12 H12A 109.51 ?
C11 C12 H12B 109.64 ?
C11 C12 H12C 109.56 ?
H12A C12 H12B 109.39 ?
H12A C12 H12C 109.34 ?
H12B C12 H12C 109.39 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.18(3) ?
O2 C1 1.40(2) yes
O2 C3 1.36(2) yes
O9 C9 1.14(3) ?
O10 C9 1.33(2) ?
O10 C11 1.52(3) ?
C1 C1a 1.44(2) ?
C1a C4a 1.39(2) ?
C1a C8 1.38(2) yes
C3 C4 1.34(2) yes
C3 C9 1.55(3) yes
C4 C4a 1.42(2) yes
C4a C5 1.39(2) yes
C5 C6 1.40(2) yes
C6 C7 1.41(2) yes
C6 C13 1.51(3) ?
C7 C8 1.36(2) yes
C7 C14 1.53(3) ?
C11 C12 1.37(2) ?
C13 F13A 1.18(4) ?
C13 F13B 1.23(3) ?
C13 F13C 1.29(4) ?
C14 F14A 1.16(4) ?
C14 F14B 1.28(4) ?
C14 F14C 1.34(4) ?
C4 H4 0.95 ?
C5 H5 0.95 ?
C8 H8 0.95 ?
C11 H11A 0.95 ?
C11 H11B 0.95 ?
C12 H12A 0.95 ?
C12 H12B 0.95 ?
C12 H12C 0.95 ?
