#------------------------------------------------------------------------------
#$Date: 2017-01-09 05:03:29 +0200 (Mon, 09 Jan 2017) $
#$Revision: 190066 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/68/7226843.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_7226843
loop_
_publ_author_name
'Galica, T.'
'Bąkowicz, J.'
'Konieczny, K.'
'Turowska-Tyrk, I.'
_publ_section_title
;
 Structural transformations in crystals induced by radiation and pressure.
 Part 5. The influence of pressure on the course of the photochemical
 reaction in crystals of 2,6-difluorocinnamic acid
;
_journal_issue                   46
_journal_name_full               CrystEngComm
_journal_page_first              8871
_journal_paper_doi               10.1039/C6CE01652A
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C9 H6 F2 O2'
_chemical_formula_weight         184.14
_chemical_properties_physical    ', Photo-sensitive'
_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   geom
_atom_sites_solution_primary     isomor
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-07-27 deposited with the CCDC.
2016-10-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.52(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.6777(15)
_cell_length_b                   19.130(10)
_cell_length_c                   10.443(11)
_cell_measurement_pressure       2100000
_cell_measurement_reflns_used    686
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      21.48
_cell_measurement_theta_min      7.23
_cell_volume                     734.7(9)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_diffrn_ambient_pressure         2100000
_diffrn_ambient_temperature      299(2)
_diffrn_detector_area_resol_mean 15.9718
_diffrn_measured_fraction_theta_full 0.495
_diffrn_measured_fraction_theta_max 0.495
_diffrn_measurement_device_type  'KM4 with Eos CCD'
_diffrn_measurement_method       'φ- and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_Laue_measured_fraction_full 0.495
_diffrn_reflns_Laue_measured_fraction_max 0.495
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2478
_diffrn_reflns_point_group_measured_fraction_full 0.495
_diffrn_reflns_point_group_measured_fraction_max 0.495
_diffrn_reflns_theta_full        23.424
_diffrn_reflns_theta_max         23.424
_diffrn_reflns_theta_min         7.482
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SCALE3 ABSPACK (Agilent Technologies, 2014).
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.112
_refine_diff_density_rms         0.029
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     84
_refine_ls_number_reflns         531
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0474
_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)+(0.0512P)²+0.3873P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1141
_reflns_Friedel_coverage         0.000
_reflns_number_gt                368
_reflns_number_total             531
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce01652a1.cif
_cod_data_source_block           0secUV_p3
_cod_depositor_comments
'Adding full bibliography for 7226837--7226849.cif.'
_cod_database_code               7226843
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_res_file
;

    0secUV_2.1GPa.res created by SHELXL-2014/7


TITL 0secUV_2.1GPa
CELL 0.71073   3.6777  19.130  10.443  90.000  90.52  90.000
ZERR    4.00   0.0015   0.010   0.011   0.000   0.05   0.000
LATT 1
SYMM x, 0.5-y, 0.5+z
SFAC C H F O
UNIT 36 24 8 8
OMIT -2 50
L.S. 6
BOND $H
HTAB
FMAP 2
PLAN -10
ACTA
TEMP 26
WGHT    0.051200    0.387300
FVAR       5.78960
F1    3    1.001461    0.732637    0.273616    11.00000    0.08423    0.05486 =
         0.05529   -0.00877   -0.02217    0.00058
F2    3    0.444661    0.674710   -0.118674    11.00000    0.07802    0.05441 =
         0.04395    0.00252   -0.01178   -0.00289
C6    1    0.721285    0.709292    0.076532    11.00000    0.04091
C1    1    0.888310    0.685566    0.186270    11.00000    0.04254
C2    1    0.944965    0.616892    0.214323    11.00000    0.05216
AFIX  43
H2    2    1.051736    0.603843    0.291772    11.00000   -1.20000
AFIX   0
C3    1    0.840703    0.566748    0.125410    11.00000    0.05542    0.03578 =
         0.08118    0.00904   -0.00598    0.00391
AFIX  43
H3    2    0.880081    0.519618    0.142414    11.00000   -1.20000
AFIX   0
C4    1    0.679574    0.586791    0.012473    11.00000    0.05173
AFIX  43
H4    2    0.612147    0.553393   -0.047943    11.00000   -1.20000
AFIX   0
C5    1    0.618132    0.656384   -0.011088    11.00000    0.04561
C7    1    0.641191    0.782571    0.042972    11.00000    0.04825
AFIX  43
H7    2    0.506216    0.790172   -0.031471    11.00000   -1.20000
AFIX   0
C8    1    0.744316    0.839491    0.109529    11.00000    0.05156
AFIX  43
H8    2    0.883010    0.835282    0.184038    11.00000   -1.20000
AFIX   0
C9    1    0.631760    0.908939    0.061329    11.00000    0.05764    0.03670 =
         0.05245   -0.00283   -0.00248   -0.00154
O1    4    0.733650    0.960120    0.140623    11.00000    0.10510    0.03890 =
         0.06598   -0.01154   -0.03317    0.00420
AFIX 147
H1    2    0.690621    0.998053    0.107205    11.00000   -1.50000
AFIX   0
O2    4    0.459963    0.918934   -0.035062    11.00000    0.08559    0.04637 =
         0.05211   -0.00159   -0.02506    0.00067

HKLF 4

REM  0secUV_2.1GPa
REM R1 =  0.0474 for     368 Fo > 4sig(Fo)  and  0.0835 for all     531 data
REM     84 parameters refined using      0 restraints

END

WGHT      0.0512      0.3873

REM Instructions for potential hydrogen bonds
EQIV $1 x+1, -y+3/2, z+1/2
HTAB C2 O2_$1
HTAB C8 F1
EQIV $2 -x+1, -y+2, -z
HTAB O1 O2_$2

REM Highest difference peak  0.145,  deepest hole -0.112,  1-sigma level  0.029
Q1    1   0.7599  0.6374  0.2873  11.00000  0.05    0.14
Q2    1   1.0819  0.6385  0.2432  11.00000  0.05    0.11
Q3    1   0.7653  0.6678  0.2204  11.00000  0.05    0.10
Q4    1   0.3610  0.7903  0.0176  11.00000  0.05    0.10
Q5    1   0.9197  0.5906  0.1801  11.00000  0.05    0.09
Q6    1   0.5727  0.7205 -0.0181  11.00000  0.05    0.09
Q7    1   1.3551  0.7598  0.3416  11.00000  0.05    0.09
Q8    1   0.9107  0.7076  0.1118  11.00000  0.05    0.09
Q9    1   0.6349  0.7038  0.0190  11.00000  0.05    0.09
Q10   1   0.7979  0.6274 -0.1349  11.00000  0.05    0.08
;
_shelx_res_checksum              33815
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
F1 F 1.0015(7) 0.73264(13) 0.2736(3) 0.0649(11) Uani 1 1 d . .
F2 F 0.4447(7) 0.67471(12) -0.1187(3) 0.0589(11) Uani 1 1 d . .
C6 C 0.7213(10) 0.7093(2) 0.0765(5) 0.0409(12) Uiso 1 1 d . .
C1 C 0.8883(11) 0.6856(2) 0.1863(6) 0.0425(12) Uiso 1 1 d . .
C2 C 0.9450(11) 0.6169(3) 0.2143(6) 0.0522(14) Uiso 1 1 d . .
H2 H 1.0517 0.6038 0.2918 0.063 Uiso 1 1 calc R U
C3 C 0.8407(12) 0.5667(2) 0.1254(7) 0.0575(19) Uani 1 1 d . .
H3 H 0.8801 0.5196 0.1424 0.069 Uiso 1 1 calc R U
C4 C 0.6796(11) 0.5868(3) 0.0125(6) 0.0517(14) Uiso 1 1 d . .
H4 H 0.6121 0.5534 -0.0479 0.062 Uiso 1 1 calc R U
C5 C 0.6181(11) 0.6564(3) -0.0111(7) 0.0456(14) Uiso 1 1 d . .
C7 C 0.6412(11) 0.7826(2) 0.0430(6) 0.0482(13) Uiso 1 1 d . .
H7 H 0.5062 0.7902 -0.0315 0.058 Uiso 1 1 calc R U
C8 C 0.7443(11) 0.8395(3) 0.1095(6) 0.0516(13) Uiso 1 1 d . .
H8 H 0.8830 0.8353 0.1840 0.062 Uiso 1 1 calc R U
C9 C 0.6318(14) 0.9089(2) 0.0613(8) 0.0489(19) Uani 1 1 d . .
O1 O 0.7337(10) 0.96012(17) 0.1406(4) 0.0702(15) Uani 1 1 d . .
H1 H 0.6906 0.9981 0.1072 0.105 Uiso 1 1 calc R U
O2 O 0.4600(10) 0.91893(15) -0.0351(5) 0.0615(14) Uani 1 1 d . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0842(17) 0.055(2) 0.055(4) -0.0088(13) -0.0222(17) 0.0006(13)
F2 0.0780(17) 0.054(2) 0.044(4) 0.0025(12) -0.0118(17) -0.0029(12)
C3 0.055(3) 0.036(4) 0.081(7) 0.009(2) -0.006(3) 0.004(2)
C9 0.058(3) 0.037(4) 0.052(8) -0.003(3) -0.002(3) -0.002(2)
O1 0.105(3) 0.039(3) 0.066(5) -0.0115(19) -0.033(2) 0.0042(19)
O2 0.086(2) 0.046(3) 0.052(5) -0.0016(16) -0.025(3) 0.0007(15)
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
C1 C6 C5 114.8(5)
C1 C6 C7 126.9(4)
C5 C6 C7 118.4(5)
F1 C1 C2 117.0(5)
F1 C1 C6 118.6(4)
C2 C1 C6 124.4(5)
C1 C2 C3 118.8(6)
C1 C2 H2 120.6
C3 C2 H2 120.6
C4 C3 C2 119.8(5)
C4 C3 H3 120.1
C2 C3 H3 120.1
C3 C4 C5 119.7(5)
C3 C4 H4 120.2
C5 C4 H4 120.2
F2 C5 C4 118.9(5)
F2 C5 C6 118.7(5)
C4 C5 C6 122.4(6)
C8 C7 C6 126.3(6)
C8 C7 H7 116.8
C6 C7 H7 116.8
C7 C8 C9 118.4(6)
C7 C8 H8 120.8
C9 C8 H8 120.8
O2 C9 O1 123.2(5)
O2 C9 C8 125.0(5)
O1 C9 C8 111.8(7)
C9 O1 H1 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C1 1.345(6)
F2 C5 1.334(6)
C6 C1 1.373(7)
C6 C5 1.414(8)
C6 C7 1.474(6)
C1 C2 1.362(6)
C2 C3 1.387(8)
C2 H2 0.9300
C3 C4 1.370(8)
C3 H3 0.9300
C4 C5 1.372(6)
C4 H4 0.9300
C7 C8 1.345(7)
C7 H7 0.9300
C8 C9 1.478(8)
C8 H8 0.9300
C9 O2 1.199(7)
C9 O1 1.334(7)
O1 H1 0.8200
