#------------------------------------------------------------------------------
#$Date: 2016-07-01 04:33:22 +0300 (Fri, 01 Jul 2016) $
#$Revision: 184084 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/05/2020546.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_2020546
loop_
_publ_author_name
'Galica, Tomasz'
'Bakowicz, Julia'
'Broda, Piotr'
'Turowska-Tyrk, Ilona'
_publ_section_title
;
 Monitoring photo-induced transformations in crystals of
 2,6-difluorocinnamic acid under ambient conditions
;
_journal_coeditor_code           YF3104
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              593
_journal_page_last               599
_journal_paper_doi               10.1107/S2053229616010019
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C18 H12 F4 O4, 0.5C7 H8'
_chemical_formula_moiety         'C18 H12 F4 O4, 0.5(C7 H8)'
_chemical_formula_sum            'C21.5 H16 F4 O4'
_chemical_formula_weight         414.34
_chemical_name_systematic
;
3,4-Bis(2,6-difluorophenyl)cyclobutane-1,2-dicarboxylic acid
toluene hemisolvate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                112.145(8)
_cell_angle_beta                 96.843(6)
_cell_angle_gamma                97.960(7)
_cell_formula_units_Z            2
_cell_length_a                   7.6212(5)
_cell_length_b                   10.3137(10)
_cell_length_c                   13.1849(10)
_cell_measurement_reflns_used    2280
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      26.8290
_cell_measurement_theta_min      2.1510
_cell_volume                     933.94(15)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2014)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012),
and Mercury (Macrae et al.,  2006) and
CrystalExplorer (Wolff et al.,  2012)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS2013 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      299(2)
_diffrn_detector_area_resol_mean 15.9718
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'KM-4 with an Eos CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6370
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         2.159
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(Scale3 AbsPack; Agilent, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_description       block
_exptl_crystal_F_000             426
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.175
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         3661
_refine_ls_number_restraints     49
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0479
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0590P)²+0.2977P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1274
_reflns_number_gt                2747
_reflns_number_total             3661
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yf3104sup1.cif
_cod_data_source_block           III
_cod_original_cell_volume        933.94(14)
_cod_database_code               2020546
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.4304(3) 0.4154(2) 0.16562(17) 0.0410(5) Uani d 1 . .
C C2 0.3003(3) 0.4967(3) 0.1772(2) 0.0547(6) Uani d 1 . .
C C3 0.3394(4) 0.6275(3) 0.1716(2) 0.0605(7) Uani d 1 . .
C C4 0.5055(4) 0.6752(3) 0.1541(2) 0.0566(6) Uani d 1 . .
C C5 0.6305(3) 0.5885(2) 0.14126(18) 0.0435(5) Uani d 1 . .
C C6 0.6003(3) 0.4554(2) 0.14628(15) 0.0355(4) Uani d 1 . .
C C7 0.7432(3) 0.3663(2) 0.13256(16) 0.0352(4) Uani d 1 . .
C C8 0.6845(3) 0.2040(2) 0.05624(17) 0.0365(4) Uani d 1 . .
C C9 0.8035(3) 0.1506(2) -0.02623(17) 0.0391(5) Uani d 1 . .
C C10 0.6987(3) 0.3518(3) 0.41310(19) 0.0507(5) Uani d 1 . .
C C11 0.6834(3) 0.4328(4) 0.5210(2) 0.0623(7) Uani d 1 . .
C C12 0.7511(3) 0.5765(3) 0.5657(2) 0.0632(7) Uani d 1 . .
C C13 0.8365(4) 0.6384(3) 0.5049(2) 0.0612(7) Uani d 1 . .
C C14 0.8496(3) 0.5530(2) 0.39804(18) 0.0478(5) Uani d 1 . .
C C15 0.7809(3) 0.4073(2) 0.34653(16) 0.0393(5) Uani d 1 . .
C C16 0.8157(3) 0.3271(2) 0.23208(16) 0.0355(4) Uani d 1 . .
C C17 0.7307(3) 0.1690(2) 0.16231(16) 0.0358(4) Uani d 1 . .
C C18 0.8528(3) 0.0648(2) 0.15314(17) 0.0387(4) Uani d 1 . .
F F1 0.39116(16) 0.28763(13) 0.17349(12) 0.0568(4) Uani d 1 . .
F F2 0.79258(19) 0.63608(14) 0.12238(13) 0.0638(4) Uani d 1 . .
F F3 0.6311(2) 0.20932(17) 0.37129(13) 0.0812(5) Uani d 1 . .
F F4 0.9399(2) 0.61154(14) 0.33808(12) 0.0654(4) Uani d 1 . .
O O1 0.7241(2) 0.03875(19) -0.11596(14) 0.0642(5) Uani d 1 . .
O O2 0.9622(2) 0.20440(17) -0.00828(15) 0.0607(5) Uani d 1 . .
O O3 0.7766(2) -0.06603(16) 0.08604(15) 0.0565(5) Uani d 1 . .
O O4 1.0097(2) 0.09963(17) 0.20065(14) 0.0575(4) Uani d 1 . .
H H2 0.191(4) 0.461(3) 0.189(2) 0.063(7) Uiso d 1 . .
H H3 0.252(4) 0.691(3) 0.181(2) 0.083(9) Uiso d 1 . .
H H4 0.547(4) 0.764(3) 0.151(2) 0.073(8) Uiso d 1 . .
H H7 0.838(3) 0.413(2) 0.1097(16) 0.030(5) Uiso d 1 . .
H H8 0.560(3) 0.167(2) 0.0193(17) 0.038(5) Uiso d 1 . .
H HO1 0.812(5) 0.005(4) -0.154(3) 0.097(11) Uiso d 1 . .
H H11 0.622(4) 0.381(3) 0.557(2) 0.073(8) Uiso d 1 . .
H H12 0.738(4) 0.631(3) 0.642(3) 0.078(8) Uiso d 1 . .
H H13 0.885(4) 0.733(4) 0.534(3) 0.083(10) Uiso d 1 . .
H H16 0.943(3) 0.333(2) 0.2351(16) 0.031(5) Uiso d 1 . .
H H17 0.629(3) 0.136(2) 0.1828(17) 0.040(5) Uiso d 1 . .
H HO2 0.855(5) -0.112(4) 0.071(3) 0.119(14) Uiso d 1 . .
C C19 0.901(2) 0.9424(15) 0.4049(12) 0.129(4) Uani d 0.5 A 1
H H19 0.8878 0.9004 0.3277 0.155 Uiso calc 0.5 A 1
C C20 0.7509(15) 0.9655(12) 0.4532(11) 0.146(4) Uani d 0.5 A 1
H H20 0.6364 0.9403 0.4095 0.175 Uiso calc 0.5 A 1
C C21 0.7744(19) 1.0250(14) 0.5644(12) 0.162(4) Uani d 0.5 A 1
H H21 0.6734 1.0372 0.5976 0.195 Uiso calc 0.5 A 1
C C22 0.9382(19) 1.0678(9) 0.6301(8) 0.125(3) Uani d 0.5 A 1
H H22 0.9481 1.1154 0.7067 0.150 Uiso calc 0.5 A 1
C C23 1.094(2) 1.0423(17) 0.5860(11) 0.125(4) Uani d 0.5 A 1
H H23 1.2062 1.0652 0.6318 0.150 Uiso calc 0.5 A 1
C C24 1.0733(17) 0.9811(10) 0.4705(11) 0.146(3) Uani d 0.5 A 1
C C25 1.232(2) 0.953(2) 0.4169(16) 0.210(7) Uani d 0.5 A 1
H H25A 1.2655 0.8680 0.4202 0.315 Uiso calc 0.5 A 1
H H25B 1.3311 1.0324 0.4552 0.315 Uiso calc 0.5 A 1
H H25C 1.2028 0.9400 0.3404 0.315 Uiso calc 0.5 A 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
F1 C1 C2 . . 118.18(19)
F1 C1 C6 . . 117.67(17)
C2 C1 C6 . . 124.2(2)
C1 C2 C3 . . 118.8(2)
C1 C2 H2 . . 118.0(17)
C3 C2 H2 . . 123.2(17)
C4 C3 C2 . . 120.3(2)
C4 C3 H3 . . 117.8(17)
C2 C3 H3 . . 121.9(18)
C3 C4 C5 . . 118.6(2)
C3 C4 H4 . . 127.2(17)
C5 C4 H4 . . 114.2(17)
F2 C5 C4 . . 117.8(2)
F2 C5 C6 . . 118.06(18)
C4 C5 C6 . . 124.1(2)
C1 C6 C5 . . 114.00(18)
C1 C6 C7 . . 124.46(17)
C5 C6 C7 . . 121.53(18)
C6 C7 C8 . . 117.61(16)
C6 C7 C16 . . 118.65(16)
C8 C7 C16 . . 89.48(14)
C6 C7 H7 . . 106.0(12)
C8 C7 H7 . . 112.5(11)
C16 C7 H7 . . 112.2(11)
C9 C8 C7 . . 113.86(16)
C9 C8 C17 . . 112.19(16)
C7 C8 C17 . . 89.10(14)
C9 C8 H8 . . 109.0(12)
C7 C8 H8 . . 118.7(12)
C17 C8 H8 . . 112.7(12)
O2 C9 O1 . . 123.52(19)
O2 C9 C8 . . 122.14(18)
O1 C9 C8 . . 114.28(18)
F3 C10 C15 . . 118.5(2)
F3 C10 C11 . . 117.8(2)
C15 C10 C11 . . 123.7(2)
C12 C11 C10 . . 119.2(3)
C12 C11 H11 . . 126.0(18)
C10 C11 H11 . . 114.8(18)
C11 C12 C13 . . 120.3(2)
C11 C12 H12 . . 117.2(17)
C13 C12 H12 . . 122.5(17)
C12 C13 C14 . . 118.4(3)
C12 C13 H13 . . 121(2)
C14 C13 H13 . . 120(2)
F4 C14 C13 . . 119.2(2)
F4 C14 C15 . . 116.22(19)
C13 C14 C15 . . 124.6(2)
C10 C15 C14 . . 113.9(2)
C10 C15 C16 . . 127.55(19)
C14 C15 C16 . . 118.30(19)
C15 C16 C17 . . 122.86(17)
C15 C16 C7 . . 120.12(16)
C17 C16 C7 . . 90.26(14)
C15 C16 H16 . . 109.3(12)
C17 C16 H16 . . 105.3(11)
C7 C16 H16 . . 106.6(12)
C18 C17 C16 . . 116.38(16)
C18 C17 C8 . . 116.18(16)
C16 C17 C8 . . 89.94(15)
C18 C17 H17 . . 107.1(13)
C16 C17 H17 . . 114.8(13)
C8 C17 H17 . . 112.0(13)
O4 C18 O3 . . 123.34(19)
O4 C18 C17 . . 123.23(18)
O3 C18 C17 . . 113.37(18)
C9 O1 HO1 . . 107(2)
C18 O3 HO2 . . 108(3)
C20 C19 C24 . . 120.9(10)
C20 C19 H19 . . 119.5
C24 C19 H19 . . 119.5
C21 C20 C19 . . 118.2(11)
C21 C20 H20 . . 120.9
C19 C20 H20 . . 120.9
C20 C21 C22 . . 122.6(10)
C20 C21 H21 . . 118.7
C22 C21 H21 . . 118.7
C21 C22 C23 . . 121.5(10)
C21 C22 H22 . . 119.2
C23 C22 H22 . . 119.2
C24 C23 C22 . . 116.9(10)
C24 C23 H23 . . 121.6
C22 C23 H23 . . 121.6
C22 C24 C21 2_776 2_776 64.5(9)
C22 C24 C23 2_776 2_776 66.2(11)
C21 C24 C23 2_776 2_776 130.1(15)
C22 C24 C23 2_776 . 177.0(11)
C21 C24 C23 2_776 . 113.3(11)
C23 C24 C23 2_776 . 115.8(10)
C22 C24 C19 2_776 . 62.4(10)
C21 C24 C19 2_776 . 126.8(10)
C23 C24 C19 2_776 . 6.0(11)
C23 C24 C19 . . 119.7(8)
C22 C24 C24 2_776 2_776 125.8(18)
C21 C24 C24 2_776 2_776 166.6(16)
C23 C24 C24 2_776 2_776 59.7(9)
C23 C24 C24 . 2_776 56.1(11)
C19 C24 C24 . 2_776 63.8(12)
C22 C24 C20 2_776 2_776 121.7(13)
C21 C24 C20 2_776 2_776 57.2(9)
C23 C24 C20 2_776 2_776 168.4(13)
C23 C24 C20 . 2_776 56.0(8)
C19 C24 C20 . 2_776 174.4(8)
C24 C24 C20 2_776 2_776 111.6(14)
C22 C24 C25 2_776 . 57.6(11)
C21 C24 C25 2_776 . 8.9(11)
C23 C24 C25 2_776 . 123.8(13)
C23 C24 C25 . . 120.3(11)
C19 C24 C25 . . 119.9(10)
C24 C24 C25 2_776 . 175.5(15)
C20 C24 C25 2_776 . 64.6(10)
C22 C24 C19 2_776 2_776 173.3(12)
C21 C24 C19 2_776 2_776 112.4(15)
C23 C24 C19 2_776 2_776 115.8(12)
C23 C24 C19 . 2_776 4.1(12)
C19 C24 C19 . 2_776 120.1(10)
C24 C24 C19 2_776 2_776 56.3(7)
C20 C24 C19 2_776 2_776 55.4(8)
C25 C24 C19 . 2_776 119.9(14)
C24 C25 H25A . . 109.5
C24 C25 H25B . . 109.5
H25A C25 H25B . . 109.5
C24 C25 H25C . . 109.5
H25A C25 H25C . . 109.5
H25B C25 H25C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 F1 . 1.355(2)
C1 C2 . 1.371(3)
C1 C6 . 1.386(3)
C2 C3 . 1.373(4)
C2 H2 . 0.92(3)
C3 C4 . 1.372(4)
C3 H3 . 0.99(3)
C4 C5 . 1.377(3)
C4 H4 . 0.95(3)
C5 F2 . 1.351(2)
C5 C6 . 1.388(3)
C6 C7 . 1.504(3)
C7 C8 . 1.559(3)
C7 C16 . 1.574(3)
C7 H7 . 0.95(2)
C8 C9 . 1.493(3)
C8 C17 . 1.584(3)
C8 H8 . 0.96(2)
C9 O2 . 1.213(2)
C9 O1 . 1.306(3)
C10 F3 . 1.356(3)
C10 C15 . 1.379(3)
C10 C11 . 1.380(3)
C11 C12 . 1.367(4)
C11 H11 . 0.95(3)
C12 C13 . 1.367(4)
C12 H12 . 0.98(3)
C13 C14 . 1.376(3)
C13 H13 . 0.90(3)
C14 F4 . 1.355(3)
C14 C15 . 1.386(3)
C15 C16 . 1.499(3)
C16 C17 . 1.536(3)
C16 H16 . 0.96(2)
C17 C18 . 1.497(3)
C17 H17 . 0.91(2)
C18 O4 . 1.218(2)
C18 O3 . 1.304(3)
O1 HO1 . 0.91(4)
O3 HO2 . 0.81(4)
C19 C20 . 1.383(9)
C19 C24 . 1.396(9)
C19 H19 . 0.9300
C20 C21 . 1.336(9)
C20 H20 . 0.9300
C21 C22 . 1.343(9)
C21 H21 . 0.9300
C22 C23 . 1.398(9)
C22 H22 . 0.9300
C23 C24 . 1.391(9)
C23 H23 . 0.9300
C24 C22 2_776 1.215(16)
C24 C21 2_776 1.30(2)
C24 C23 2_776 1.34(3)
C24 C24 2_776 1.45(2)
C24 C20 2_776 1.47(2)
C24 C25 . 1.482(9)
C24 C19 2_776 1.50(2)
C25 H25A . 0.9600
C25 H25B . 0.9600
C25 H25C . 0.9600

_cod_database_fobs_code 2020546
