#------------------------------------------------------------------------------
#$Date: 2016-07-01 04:33:22 +0300 (Fri, 01 Jul 2016) $
#$Revision: 184084 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/05/2020544.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_2020544
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          'C9 H6 F2 O2'
_chemical_formula_moiety         'C9 H6 F2 O2'
_chemical_formula_sum            'C9 H6 F2 O2'
_chemical_formula_weight         184.14
_chemical_name_common
;
2,6-Difluorocinnamic acid
;
_chemical_name_systematic
;
3-(2,6-Difluorophenyl)prop-2-enoic acid
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 92.221(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.8856(3)
_cell_length_b                   19.2920(11)
_cell_length_c                   10.9859(6)
_cell_measurement_reflns_used    1694
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      27.7876
_cell_measurement_theta_min      1.8513
_cell_volume                     822.90(9)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0254
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5660
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.111
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(Scale3 AbsPack; Agilent, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.156
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         1619
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0408
_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)+(0.0452P)²+0.0206P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0965
_reflns_number_gt                1000
_reflns_number_total             1619
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yf3104sup1.cif
_cod_data_source_block           I
_cod_database_code               2020544
_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+1/2, z+1/2'
'-x, -y, -z'
'-x, y-1/2, -z-1/2'
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
C C1 0.6089(5) 0.68850(11) 0.31454(17) 0.0548(5) Uani d 1
C C2 0.5472(6) 0.62027(13) 0.2868(2) 0.0684(6) Uani d 1
C C3 0.6458(6) 0.57058(13) 0.3707(2) 0.0734(6) Uani d 1
C C4 0.8057(6) 0.58904(12) 0.4791(2) 0.0662(6) Uani d 1
C C5 0.8668(5) 0.65801(10) 0.50136(18) 0.0542(5) Uani d 1
C C6 0.7719(4) 0.71153(9) 0.42229(16) 0.0476(4) Uani d 1
C C7 0.8488(5) 0.78374(10) 0.45376(18) 0.0519(5) Uani d 1
C C8 0.7703(5) 0.84073(10) 0.3921(2) 0.0595(5) Uani d 1
C C9 0.8729(5) 0.90905(10) 0.43898(19) 0.0585(5) Uani d 1
F F1 0.5022(3) 0.73662(6) 0.23180(10) 0.0817(4) Uani d 1
F F2 1.0335(3) 0.67519(6) 0.60770(10) 0.0760(4) Uani d 1
O O1 0.7799(4) 0.96057(9) 0.36678(15) 0.0892(5) Uani d 1
O O2 1.0322(4) 0.91805(7) 0.53550(13) 0.0760(5) Uani d 1
H H2 0.439(5) 0.6110(11) 0.2145(18) 0.072(6) Uiso d 1
H H3 0.604(5) 0.5232(12) 0.3511(18) 0.077(6) Uiso d 1
H H4 0.871(6) 0.5584(12) 0.539(2) 0.087(7) Uiso d 1
H HO1 0.850(7) 1.0020(16) 0.404(2) 0.132(11) Uiso d 1
H H7 0.971(4) 0.7885(10) 0.5286(16) 0.060(5) Uiso d 1
H H8 0.640(5) 0.8396(10) 0.3154(19) 0.071(6) Uiso d 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'
F F 0.0171 0.0103 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
F1 C1 C2 117.59(18)
F1 C1 C6 117.99(17)
C2 C1 C6 124.4(2)
C1 C2 C3 118.6(2)
C1 C2 H2 117.2(14)
C3 C2 H2 124.2(14)
C4 C3 C2 120.5(2)
C4 C3 H3 121.0(13)
C2 C3 H3 118.5(13)
C3 C4 C5 118.5(2)
C3 C4 H4 124.1(14)
C5 C4 H4 117.4(14)
F2 C5 C4 117.67(19)
F2 C5 C6 117.62(16)
C4 C5 C6 124.71(19)
C5 C6 C1 113.26(16)
C5 C6 C7 120.84(16)
C1 C6 C7 125.89(17)
C8 C7 C6 129.07(19)
C8 C7 H7 117.8(12)
C6 C7 H7 113.1(12)
C7 C8 C9 120.98(19)
C7 C8 H8 122.1(12)
C9 C8 H8 116.9(12)
O2 C9 O1 122.40(18)
O2 C9 C8 123.76(19)
O1 C9 C8 113.83(19)
C9 O1 HO1 108.6(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 F1 1.353(2)
C1 C2 1.370(3)
C1 C6 1.393(2)
C2 C3 1.374(3)
C2 H2 0.90(2)
C3 C4 1.370(3)
C3 H3 0.95(2)
C4 C5 1.372(3)
C4 H4 0.91(2)
C5 F2 1.355(2)
C5 C6 1.390(2)
C6 C7 1.463(2)
C7 C8 1.321(3)
C7 H7 0.938(18)
C8 C9 1.465(3)
C8 H8 0.97(2)
C9 O2 1.219(2)
C9 O1 1.313(2)
O1 HO1 0.93(3)

_cod_database_fobs_code 2020544
