#------------------------------------------------------------------------------
#$Date: 2017-01-09 04:03:29 +0100 (lun 09 de ene de 2017) $
#$Revision: 190066 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/68/7226839.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_7226839
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                 91.510(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.7896(4)
_cell_length_b                   19.207(2)
_cell_length_c                   10.703(3)
_cell_measurement_pressure       1100000
_cell_measurement_reflns_used    692
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      20.07
_cell_measurement_theta_min      6.60
_cell_volume                     778.8(2)
_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         1100000
_diffrn_ambient_temperature      299(2)
_diffrn_detector_area_resol_mean 15.9718
_diffrn_measured_fraction_theta_full 0.527
_diffrn_measured_fraction_theta_max 0.527
_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  0.1250
_diffrn_reflns_av_unetI/netI     0.1056
_diffrn_reflns_Laue_measured_fraction_full 0.527
_diffrn_reflns_Laue_measured_fraction_max 0.527
_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       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3258
_diffrn_reflns_point_group_measured_fraction_full 0.527
_diffrn_reflns_point_group_measured_fraction_max 0.527
_diffrn_reflns_theta_full        24.079
_diffrn_reflns_theta_max         24.079
_diffrn_reflns_theta_min         6.654
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31151
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SCALE3 ABSPACK (Agilent Technologies, 2014).
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         655
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1633
_refine_ls_R_factor_gt           0.0908
_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)+(0.1823P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2382
_refine_ls_wR_factor_ref         0.2958
_reflns_Friedel_coverage         0.000
_reflns_number_gt                340
_reflns_number_total             655
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce01652a1.cif
_cod_data_source_block           0secUV_p2
_cod_depositor_comments
'Adding full bibliography for 7226837--7226849.cif.'
_cod_database_code               7226839
_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_1.1GPa.res created by SHELXL-2014/7


TITL 0secUV_1.1GPa
CELL 0.71073   3.7896  19.207  10.703  90.000  91.510  90.000
ZERR    4.00   0.0004   0.002   0.003   0.000   0.011   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
TEMP 26
ACTA
WGHT    0.182300
FVAR       4.33181
F1    3    0.998492    0.734492    0.272237    11.00000    0.09916    0.06267 =
         0.09815   -0.00271   -0.03031    0.00485
F2    3    0.455034    0.674869   -0.113289    11.00000    0.10017    0.05932 =
         0.08613   -0.00075   -0.02474   -0.00179
C6    1    0.723030    0.709955    0.075699    11.00000    0.04936
C1    1    0.890749    0.687097    0.180387    11.00000    0.05523
C2    1    0.951165    0.617934    0.210032    11.00000    0.06755
AFIX  43
H2    2    1.061995    0.605780    0.285468    11.00000   -1.20000
AFIX   0
C3    1    0.847311    0.568742    0.128227    11.00000    0.06231    0.04810 =
         0.12783    0.00723   -0.00505    0.00785
AFIX  43
H3    2    0.884095    0.521910    0.146389    11.00000   -1.20000
AFIX   0
C4    1    0.685583    0.588299    0.017017    11.00000    0.06483
AFIX  43
H4    2    0.622470    0.555028   -0.042616    11.00000   -1.20000
AFIX   0
C5    1    0.618527    0.657704   -0.004766    11.00000    0.05950
C7    1    0.643061    0.783321    0.042752    11.00000    0.05780
AFIX  43
H7    2    0.514151    0.790988   -0.031107    11.00000   -1.20000
AFIX   0
C8    1    0.740486    0.840653    0.110415    11.00000    0.06904
AFIX  43
H8    2    0.871316    0.837045    0.184875    11.00000   -1.20000
AFIX   0
C9    1    0.626884    0.909182    0.059070    11.00000    0.06678    0.04853 =
         0.09691    0.00294   -0.00439    0.00127
O1    4    0.731825    0.960241    0.136386    11.00000    0.11521    0.03807 =
         0.11658   -0.00988   -0.03794    0.00086
AFIX  83
H1    2    0.668669    0.997882    0.107382    11.00000   -1.50000
AFIX   0
O2    4    0.460645    0.919113   -0.033746    11.00000    0.09885    0.03815 =
         0.11167   -0.00313   -0.03700    0.00367
HKLF 4

REM  0secUV_1.1GPa
REM R1 =  0.0908 for     340 Fo > 4sig(Fo)  and  0.1633 for all     655 data
REM     83 parameters refined using      0 restraints

END

WGHT      0.1823      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  0.286,  deepest hole -0.191,  1-sigma level  0.059
Q1    1   0.9184  0.6380  0.2881  11.00000  0.05    0.29
Q2    1   0.6319  0.8321  0.1585  11.00000  0.05    0.26
Q3    1   1.4004  0.7818  0.2636  11.00000  0.05    0.22
Q4    1   0.0638  0.6959 -0.0476  11.00000  0.05    0.22
Q5    1   0.6251  0.5966  0.0880  11.00000  0.05    0.21
Q6    1   1.0760  0.7808  0.3950  11.00000  0.05    0.21
Q7    1   1.0754  0.6892  0.3803  11.00000  0.05    0.20
Q8    1   0.8061  0.6898  0.2190  11.00000  0.05    0.19
Q9    1   0.6743  0.6327 -0.1071  11.00000  0.05    0.19
Q10   1   0.4989  0.7283  0.0016  11.00000  0.05    0.19
;
_shelx_res_checksum              74076
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 0.9985(12) 0.7345(3) 0.2722(6) 0.087(3) Uani 1 1 d . .
F2 F 0.4550(13) 0.6749(2) -0.1133(7) 0.082(3) Uani 1 1 d . .
C6 C 0.7230(17) 0.7100(4) 0.0757(10) 0.049(2) Uiso 1 1 d . .
C1 C 0.891(2) 0.6871(5) 0.1804(11) 0.055(2) Uiso 1 1 d . .
C2 C 0.951(2) 0.6179(5) 0.2100(12) 0.068(3) Uiso 1 1 d . .
H2 H 1.0620 0.6058 0.2855 0.081 Uiso 1 1 calc R U
C3 C 0.847(2) 0.5687(5) 0.1282(14) 0.080(4) Uani 1 1 d . .
H3 H 0.8841 0.5219 0.1464 0.095 Uiso 1 1 calc R U
C4 C 0.686(2) 0.5883(5) 0.0170(12) 0.065(3) Uiso 1 1 d . .
H4 H 0.6225 0.5550 -0.0426 0.078 Uiso 1 1 calc R U
C5 C 0.619(2) 0.6577(5) -0.0048(12) 0.059(3) Uiso 1 1 d . .
C7 C 0.643(2) 0.7833(5) 0.0428(10) 0.058(3) Uiso 1 1 d . .
H7 H 0.5142 0.7910 -0.0311 0.069 Uiso 1 1 calc R U
C8 C 0.740(2) 0.8407(5) 0.1104(12) 0.069(3) Uiso 1 1 d . .
H8 H 0.8713 0.8370 0.1849 0.083 Uiso 1 1 calc R U
C9 C 0.627(3) 0.9092(5) 0.0591(16) 0.071(5) Uani 1 1 d . .
O1 O 0.7318(17) 0.9602(3) 0.1364(8) 0.091(3) Uani 1 1 d . .
H1 H 0.6687 0.9979 0.1074 0.136 Uiso 1 1 calc R U
O2 O 0.4606(19) 0.9191(3) -0.0337(10) 0.084(3) 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 0.099(4) 0.063(5) 0.098(8) -0.003(3) -0.030(4) 0.005(3)
F2 0.100(4) 0.059(4) 0.086(8) -0.001(3) -0.025(4) -0.002(2)
C3 0.062(5) 0.048(8) 0.128(16) 0.007(5) -0.005(7) 0.008(4)
C9 0.067(6) 0.049(9) 0.097(18) 0.003(6) -0.004(7) 0.001(4)
O1 0.115(5) 0.038(5) 0.117(11) -0.010(4) -0.038(5) 0.001(3)
O2 0.099(5) 0.038(6) 0.112(11) -0.003(3) -0.037(6) 0.004(3)
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 113.9(9)
C1 C6 C7 126.6(9)
C5 C6 C7 119.4(10)
C6 C1 C2 125.1(9)
C6 C1 F1 119.8(9)
C2 C1 F1 115.0(10)
C3 C2 C1 118.9(12)
C3 C2 H2 120.6
C1 C2 H2 120.6
C2 C3 C4 119.3(11)
C2 C3 H3 120.4
C4 C3 H3 120.4
C5 C4 C3 119.1(10)
C5 C4 H4 120.4
C3 C4 H4 120.4
F2 C5 C6 118.8(9)
F2 C5 C4 117.6(9)
C6 C5 C4 123.5(11)
C8 C7 C6 126.2(10)
C8 C7 H7 116.9
C6 C7 H7 116.9
C7 C8 C9 116.6(12)
C7 C8 H8 121.7
C9 C8 H8 121.7
O2 C9 O1 123.2(10)
O2 C9 C8 126.8(11)
O1 C9 C8 110.0(14)
C9 O1 H1 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C1 1.393(12)
F2 C5 1.343(12)
C6 C1 1.347(13)
C6 C5 1.374(14)
C6 C7 1.482(12)
C1 C2 1.383(13)
C2 C3 1.340(15)
C2 H2 0.9300
C3 C4 1.377(16)
C3 H3 0.9300
C4 C5 1.376(12)
C4 H4 0.9300
C7 C8 1.364(13)
C7 H7 0.9300
C8 C9 1.486(15)
C8 H8 0.9300
C9 O2 1.178(15)
C9 O1 1.337(15)
O1 H1 0.8200
