#------------------------------------------------------------------------------
#$Date: 2017-01-09 05:03:29 +0200 (Mon, 09 Jan 2017) $
#$Revision: 190066 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/68/7226837.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_7226837
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                 91.771(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.8271(3)
_cell_length_b                   19.192(2)
_cell_length_c                   10.816(2)
_cell_measurement_pressure       500000
_cell_measurement_reflns_used    698
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      21.09
_cell_measurement_theta_min      6.77
_cell_volume                     794.05(18)
_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         500000
_diffrn_ambient_temperature      299(2)
_diffrn_detector_area_resol_mean 15.9718
_diffrn_measured_fraction_theta_full 0.515
_diffrn_measured_fraction_theta_max 0.515
_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  0.0887
_diffrn_reflns_av_unetI/netI     0.0905
_diffrn_reflns_Laue_measured_fraction_full 0.515
_diffrn_reflns_Laue_measured_fraction_max 0.515
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3379
_diffrn_reflns_point_group_measured_fraction_full 0.515
_diffrn_reflns_point_group_measured_fraction_max 0.515
_diffrn_reflns_theta_full        24.342
_diffrn_reflns_theta_max         24.342
_diffrn_reflns_theta_min         6.653
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.11269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SCALE3 ABSPACK (Agilent Technologies, 2014).
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.110
_refine_diff_density_min         -0.119
_refine_diff_density_rms         0.029
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     89
_refine_ls_number_reflns         673
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1198
_refine_ls_R_factor_gt           0.0502
_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)+(0.0562P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1181
_reflns_Friedel_coverage         0.000
_reflns_number_gt                365
_reflns_number_total             673
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce01652a1.cif
_cod_data_source_block           0secUV_p1
_cod_depositor_comments
'Adding full bibliography for 7226837--7226849.cif.'
_cod_database_code               7226837
_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_0.5GPa.res created by SHELXL-2014/7


TITL 0secUV_0.5GPa
CELL 0.71073 3.8271 19.192 10.816 90.0 91.771 90.0
ZERR 4       0.0003  0.002  0.002  0.0  0.011  0.0
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    0.056200
FVAR       4.55262
C1    1    0.890901    0.687576    0.184517    11.00000    0.05589
C2    1    0.950286    0.619507    0.213606    11.00000    0.07008    0.06889 =
         0.06834    0.01090   -0.01066    0.00822
AFIX  43
H2    2    1.054612    0.606849    0.289093    11.00000   -1.20000
AFIX   0
C3    1    0.849334    0.569510    0.126364    11.00000    0.06880    0.04764 =
         0.09734    0.00897   -0.01219    0.00995
AFIX  43
H3    2    0.893335    0.522667    0.142404    11.00000   -1.20000
AFIX   0
C4    1    0.688676    0.588289    0.019024    11.00000    0.07006    0.04412 =
         0.07803   -0.00307   -0.00532    0.00116
AFIX  43
H4    2    0.620957    0.554618   -0.038724    11.00000   -1.20000
AFIX   0
C5    1    0.625696    0.657302   -0.004517    11.00000    0.05630
C6    1    0.723394    0.710822    0.077512    11.00000    0.04739
C7    1    0.644967    0.783167    0.043386    11.00000    0.05490
AFIX  43
H7    2    0.519498    0.790365   -0.030518    11.00000   -1.20000
AFIX   0
C8    1    0.736637    0.839547    0.108349    11.00000    0.06102
AFIX  43
H8    2    0.864925    0.835723    0.182475    11.00000   -1.20000
AFIX   0
C9    1    0.627650    0.909049    0.058818    11.00000    0.06067
F1    3    0.997067    0.735122    0.269497    11.00000    0.10270    0.06329 =
         0.07115   -0.00662   -0.02833    0.00452
F2    3    0.457979    0.674951   -0.111911    11.00000    0.10011    0.05835 =
         0.06062   -0.00213   -0.01419   -0.00443
O1    4    0.728867    0.960386    0.135466    11.00000    0.13862    0.04292 =
         0.08516   -0.01549   -0.05098    0.00300
AFIX 147
H1    2    0.664796    0.997927    0.106537    11.00000   -1.50000
AFIX   0
O2    4    0.462191    0.918497   -0.034570    11.00000    0.10500    0.04471 =
         0.08065   -0.00939   -0.03269    0.00261
HKLF 4

REM  0secUV_0.5GPa
REM R1 =  0.0502 for     365 Fo > 4sig(Fo)  and  0.1198 for all     673 data
REM     89 parameters refined using      0 restraints

END

WGHT      0.0562      0.0000

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  0.110,  deepest hole -0.119,  1-sigma level  0.029
Q1    1   1.0717  0.6915  0.1397  11.00000  0.05    0.11
Q2    1   0.5516  0.8531  0.1920  11.00000  0.05    0.10
Q3    1   0.5818  0.7869  0.2787  11.00000  0.05    0.10
Q4    1   1.1040  0.6817  0.1105  11.00000  0.05    0.10
Q5    1   0.9600  0.8714  0.2372  11.00000  0.05    0.10
Q6    1   0.4302  0.9686  0.0118  11.00000  0.05    0.09
Q7    1   0.5162  0.9138  0.0814  11.00000  0.05    0.09
Q8    1   0.7629  0.6614 -0.0731  11.00000  0.05    0.09
Q9    1   0.8771  0.6904  0.0201  11.00000  0.05    0.09
Q10   1   0.8955  0.8186 -0.0088  11.00000  0.05    0.08
;
_shelx_res_checksum              80763
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
C1 C 0.8909(11) 0.6876(3) 0.1845(7) 0.0559(13) Uiso 1 1 d . .
C2 C 0.9503(11) 0.6195(3) 0.2136(7) 0.069(2) Uani 1 1 d . .
H2 H 1.0546 0.6068 0.2891 0.083 Uiso 1 1 calc R U
C3 C 0.8493(13) 0.5695(3) 0.1264(8) 0.072(2) Uani 1 1 d . .
H3 H 0.8933 0.5227 0.1424 0.086 Uiso 1 1 calc R U
C4 C 0.6887(12) 0.5883(2) 0.0190(7) 0.064(2) Uani 1 1 d . .
H4 H 0.6210 0.5546 -0.0387 0.077 Uiso 1 1 calc R U
C5 C 0.6257(11) 0.6573(3) -0.0045(7) 0.0563(14) Uiso 1 1 d . .
C6 C 0.7234(9) 0.7108(2) 0.0775(5) 0.0474(12) Uiso 1 1 d . .
C7 C 0.6450(9) 0.7832(2) 0.0434(5) 0.0549(13) Uiso 1 1 d . .
H7 H 0.5195 0.7904 -0.0305 0.066 Uiso 1 1 calc R U
C8 C 0.7366(9) 0.8395(2) 0.1083(6) 0.0610(13) Uiso 1 1 d . .
H8 H 0.8649 0.8357 0.1825 0.073 Uiso 1 1 calc R U
C9 C 0.6276(12) 0.9090(2) 0.0588(8) 0.0607(16) Uiso 1 1 d . .
F1 F 0.9971(6) 0.73512(13) 0.2695(3) 0.0797(12) Uani 1 1 d . .
F2 F 0.4580(6) 0.67495(12) -0.1119(3) 0.0734(12) Uani 1 1 d . .
O1 O 0.7289(9) 0.96039(15) 0.1355(4) 0.0900(16) Uani 1 1 d . .
H1 H 0.6648 0.9979 0.1065 0.135 Uiso 1 1 calc R U
O2 O 0.4622(8) 0.91850(14) -0.0346(4) 0.0775(15) 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
C2 0.070(3) 0.069(5) 0.068(8) 0.011(3) -0.011(3) 0.008(3)
C3 0.069(3) 0.048(5) 0.097(9) 0.009(3) -0.012(4) 0.010(3)
C4 0.070(3) 0.044(4) 0.078(9) -0.003(3) -0.005(3) 0.001(2)
F1 0.1027(17) 0.063(2) 0.071(4) -0.0066(14) -0.0283(18) 0.0045(14)
F2 0.1001(17) 0.058(2) 0.061(4) -0.0021(13) -0.0142(19) -0.0044(12)
O1 0.139(3) 0.043(3) 0.085(5) -0.0155(17) -0.051(3) 0.0030(19)
O2 0.105(2) 0.045(3) 0.081(5) -0.0094(15) -0.033(3) 0.0026(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
F1 C1 C2 116.6(6)
F1 C1 C6 118.4(5)
C2 C1 C6 125.0(5)
C1 C2 C3 117.6(7)
C1 C2 H2 121.2
C3 C2 H2 121.2
C4 C3 C2 120.7(6)
C4 C3 H3 119.7
C2 C3 H3 119.7
C3 C4 C5 119.5(5)
C3 C4 H4 120.2
C5 C4 H4 120.2
F2 C5 C4 118.6(5)
F2 C5 C6 118.1(5)
C4 C5 C6 123.4(6)
C1 C6 C5 113.7(5)
C1 C6 C7 127.2(5)
C5 C6 C7 119.1(5)
C8 C7 C6 126.1(5)
C8 C7 H7 117.0
C6 C7 H7 117.0
C7 C8 C9 118.1(6)
C7 C8 H8 121.0
C9 C8 H8 121.0
O2 C9 O1 123.4(5)
O2 C9 C8 125.2(5)
O1 C9 C8 111.3(6)
C9 O1 H1 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 F1 1.349(6)
C1 C2 1.361(7)
C1 C6 1.380(7)
C2 C3 1.392(8)
C2 H2 0.9300
C3 C4 1.346(9)
C3 H3 0.9300
C4 C5 1.369(6)
C4 H4 0.9300
C5 F2 1.353(6)
C5 C6 1.401(8)
C6 C7 1.465(6)
C7 C8 1.331(6)
C7 H7 0.9300
C8 C9 1.492(7)
C8 H8 0.9300
C9 O2 1.189(7)
C9 O1 1.337(7)
O1 H1 0.8200
