#------------------------------------------------------------------------------
#$Date: 2020-12-05 17:08:55 +0200 (Sat, 05 Dec 2020) $
#$Revision: 259566 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/97/1559704.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_1559704
loop_
_publ_author_name
'Sysoiev, Dmytro'
'Huhn, Thomas'
_publ_section_title
;
 Basic enemies of photochromism: irreversible transformation of
 fluorinated diarylethenes to polyenic enamines and enols.
;
_journal_issue                   11
_journal_name_full
'Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology'
_journal_page_first              1511
_journal_page_last               1516
_journal_paper_doi               10.1039/d0pp00292e
_journal_volume                  19
_journal_year                    2020
_chemical_formula_moiety         'C29 H34 F6 O6'
_chemical_formula_sum            'C29 H34 F6 O6'
_chemical_formula_weight         592.56
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2014-12-05 deposited with the CCDC.	2020-10-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.844(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.3540(16)
_cell_length_b                   12.3394(10)
_cell_length_c                   10.9586(8)
_cell_measurement_reflns_used    10025
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      1.92
_cell_volume                     2826.1(4)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1355
_diffrn_reflns_av_unetI/netI     0.0788
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17707
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.767
_diffrn_reflns_theta_min         1.917
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.9829
_exptl_absorpt_correction_T_min  0.9680
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
'X-SHAPE 2.07 (03-Aug-2005) Stoe & Cie, Darmstadt, Germany'
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_description       prism
_exptl_crystal_F_000             1240
_exptl_crystal_preparation       photochromic
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CHCl3/hexanes'
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.400
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2669
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.953
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0551
_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)+(0.0640P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1255
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1756
_reflns_number_total             2669
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0pp00292e2.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1559704
_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.
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.18713(11) 0.6781(2) 0.0575(2) 0.0218(6) Uani 1 1 d . . . . .
H1 H 0.2256 0.6591 0.0265 0.026 Uiso 1 1 calc R U . . .
C2 C 0.14026(11) 0.7329(2) -0.0429(2) 0.0203(5) Uani 1 1 d . . . . .
C3 C 0.10837(11) 0.8269(2) -0.0448(2) 0.0203(5) Uani 1 1 d . . . . .
H3 H 0.1099 0.8745 0.0214 0.024 Uiso 1 1 calc R U . . .
C4 C 0.07148(10) 0.8393(2) -0.1693(2) 0.0190(5) Uani 1 1 d . . . . .
C5 C 0.08472(10) 0.7522(2) -0.2356(2) 0.0195(5) Uani 1 1 d . . . . .
C6 C 0.06815(11) 0.7211(2) -0.3697(2) 0.0234(6) Uani 1 1 d . . . . .
H6A H 0.1073 0.7194 -0.4016 0.028 Uiso 1 1 calc R U . . .
H6B H 0.0411 0.7773 -0.4147 0.028 Uiso 1 1 calc R U . . .
C7 C 0.03421(13) 0.6126(2) -0.3985(3) 0.0304(7) Uani 1 1 d . . . . .
H7A H 0.0256 0.6002 -0.4869 0.046 Uiso 1 1 calc R U . . .
H7B H -0.0053 0.6136 -0.3697 0.046 Uiso 1 1 calc R U . . .
H7C H 0.0610 0.5556 -0.3571 0.046 Uiso 1 1 calc R U . . .
C8 C 0.02982(11) 0.9313(2) -0.2148(2) 0.0208(5) Uani 1 1 d . . . . .
C9 C 0.05260(12) 1.0437(2) -0.1819(3) 0.0309(7) Uani 1 1 d . . . . .
C10 C 0.0000 1.1200(3) -0.2500 0.0244(8) Uani 1 2 d S T P . .
C11 C 0.24799(12) 0.7092(2) 0.2569(2) 0.0278(6) Uani 1 1 d . . . . .
H11A H 0.2570 0.7620 0.3238 0.033 Uiso 1 1 calc R U . . .
H11B H 0.2877 0.6939 0.2303 0.033 Uiso 1 1 calc R U . . .
C12 C 0.22319(11) 0.6053(2) 0.3056(2) 0.0232(6) Uani 1 1 d . . . . .
C13 C 0.20336(12) 0.5309(2) 0.1940(2) 0.0257(6) Uani 1 1 d . . . . .
H13A H 0.2411 0.5087 0.1639 0.031 Uiso 1 1 calc R U . . .
H13B H 0.1835 0.4664 0.2195 0.031 Uiso 1 1 calc R U . . .
C14 C 0.27790(13) 0.5532(3) 0.3994(3) 0.0330(7) Uani 1 1 d . . . . .
H14A H 0.2903 0.6003 0.4699 0.050 Uiso 1 1 calc R U . . .
H14B H 0.3138 0.5416 0.3606 0.050 Uiso 1 1 calc R U . . .
H14C H 0.2639 0.4851 0.4266 0.050 Uiso 1 1 calc R U . . .
C15 C 0.16608(13) 0.6294(3) 0.3658(3) 0.0352(7) Uani 1 1 d . . . . .
H15A H 0.1793 0.6768 0.4358 0.053 Uiso 1 1 calc R U . . .
H15B H 0.1502 0.5629 0.3934 0.053 Uiso 1 1 calc R U . . .
H15C H 0.1329 0.6637 0.3059 0.053 Uiso 1 1 calc R U . . .
F1 F 0.10883(8) 1.06492(15) -0.2157(3) 0.0719(8) Uani 1 1 d . . . . .
F2 F 0.06352(12) 1.06178(16) -0.05763(18) 0.0699(7) Uani 1 1 d . . . . .
F3 F -0.02159(8) 1.18382(19) -0.17030(18) 0.0592(6) Uani 1 1 d . . . . .
O1 O 0.12686(7) 0.68486(14) -0.15878(15) 0.0205(4) Uani 1 1 d . . . . .
O2 O 0.20264(8) 0.75403(14) 0.15416(16) 0.0248(4) Uani 1 1 d . . . . .
O3 O 0.15919(8) 0.58351(15) 0.09465(16) 0.0248(4) Uani 1 1 d . . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O3 112.55(19) . . ?
O2 C1 C2 105.9(2) . . ?
O3 C1 C2 109.22(19) . . ?
O2 C1 H1 109.7 . . ?
O3 C1 H1 109.7 . . ?
C2 C1 H1 109.7 . . ?
C3 C2 O1 110.4(2) . . ?
C3 C2 C1 131.7(2) . . ?
O1 C2 C1 117.9(2) . . ?
C2 C3 C4 106.5(2) . . ?
C2 C3 H3 126.7 . . ?
C4 C3 H3 126.7 . . ?
C5 C4 C3 106.8(2) . . ?
C5 C4 C8 127.5(2) . . ?
C3 C4 C8 125.6(2) . . ?
C4 C5 O1 109.4(2) . . ?
C4 C5 C6 134.3(2) . . ?
O1 C5 C6 116.1(2) . . ?
C5 C6 C7 115.9(2) . . ?
C5 C6 H6A 108.3 . . ?
C7 C6 H6A 108.3 . . ?
C5 C6 H6B 108.3 . . ?
C7 C6 H6B 108.3 . . ?
H6A C6 H6B 107.4 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C8 C8 C4 129.17(13) 2_554 . ?
C8 C8 C9 111.23(14) 2_554 . ?
C4 C8 C9 119.6(2) . . ?
F2 C9 F1 105.4(2) . . ?
F2 C9 C8 112.2(2) . . ?
F1 C9 C8 112.2(2) . . ?
F2 C9 C10 110.2(2) . . ?
F1 C9 C10 110.5(2) . . ?
C8 C9 C10 106.5(2) . . ?
F3 C10 F3 107.2(3) . 2_554 ?
F3 C10 C9 111.24(13) . . ?
F3 C10 C9 111.41(14) 2_554 . ?
F3 C10 C9 111.41(14) . 2_554 ?
F3 C10 C9 111.24(13) 2_554 2_554 ?
C9 C10 C9 104.4(3) . 2_554 ?
O2 C11 C12 111.8(2) . . ?
O2 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
O2 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 106.6(2) . . ?
C13 C12 C15 110.5(2) . . ?
C11 C12 C15 110.6(2) . . ?
C13 C12 C14 109.6(2) . . ?
C11 C12 C14 108.4(2) . . ?
C15 C12 C14 111.0(2) . . ?
O3 C13 C12 111.6(2) . . ?
O3 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
O3 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C2 O1 C5 106.85(19) . . ?
C1 O2 C11 110.6(2) . . ?
C1 O3 C13 109.96(18) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.402(3) . ?
C1 O3 1.409(3) . ?
C1 C2 1.489(3) . ?
C1 H1 0.9800 . ?
C2 C3 1.343(4) . ?
C2 O1 1.377(3) . ?
C3 C4 1.437(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.359(3) . ?
C4 C8 1.465(3) . ?
C5 O1 1.378(3) . ?
C5 C6 1.489(3) . ?
C6 C7 1.525(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C8 1.347(5) 2_554 ?
C8 C9 1.490(4) . ?
C9 F2 1.352(3) . ?
C9 F1 1.353(3) . ?
C9 C10 1.536(4) . ?
C10 F3 1.327(3) . ?
C10 F3 1.327(3) 2_554 ?
C10 C9 1.536(4) 2_554 ?
C11 O2 1.437(3) . ?
C11 C12 1.524(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.518(4) . ?
C12 C15 1.530(4) . ?
C12 C14 1.531(4) . ?
C13 O3 1.440(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 C3 -10.0(3) . . . . ?
O3 C1 C2 C3 111.4(3) . . . . ?
O2 C1 C2 O1 166.99(18) . . . . ?
O3 C1 C2 O1 -71.6(3) . . . . ?
O1 C2 C3 C4 0.8(3) . . . . ?
C1 C2 C3 C4 178.0(2) . . . . ?
C2 C3 C4 C5 -1.3(3) . . . . ?
C2 C3 C4 C8 -179.1(2) . . . . ?
C3 C4 C5 O1 1.2(2) . . . . ?
C8 C4 C5 O1 179.0(2) . . . . ?
C3 C4 C5 C6 -172.8(2) . . . . ?
C8 C4 C5 C6 5.0(4) . . . . ?
C4 C5 C6 C7 -123.8(3) . . . . ?
O1 C5 C6 C7 62.5(3) . . . . ?
C5 C4 C8 C8 47.6(5) . . . 2_554 ?
C3 C4 C8 C8 -135.0(3) . . . 2_554 ?
C5 C4 C8 C9 -133.1(3) . . . . ?
C3 C4 C8 C9 44.3(3) . . . . ?
C8 C8 C9 F2 116.7(3) 2_554 . . . ?
C4 C8 C9 F2 -62.8(3) . . . . ?
C8 C8 C9 F1 -125.0(3) 2_554 . . . ?
C4 C8 C9 F1 55.6(3) . . . . ?
C8 C8 C9 C10 -4.0(3) 2_554 . . . ?
C4 C8 C9 C10 176.60(18) . . . . ?
F2 C9 C10 F3 -0.2(3) . . . . ?
F1 C9 C10 F3 -116.3(2) . . . . ?
C8 C9 C10 F3 121.6(2) . . . . ?
F2 C9 C10 F3 119.3(3) . . . 2_554 ?
F1 C9 C10 F3 3.3(3) . . . 2_554 ?
C8 C9 C10 F3 -118.8(2) . . . 2_554 ?
F2 C9 C10 C9 -120.5(2) . . . 2_554 ?
F1 C9 C10 C9 123.4(2) . . . 2_554 ?
C8 C9 C10 C9 1.35(11) . . . 2_554 ?
O2 C11 C12 C13 52.9(3) . . . . ?
O2 C11 C12 C15 -67.2(3) . . . . ?
O2 C11 C12 C14 170.9(2) . . . . ?
C11 C12 C13 O3 -53.7(3) . . . . ?
C15 C12 C13 O3 66.6(3) . . . . ?
C14 C12 C13 O3 -170.9(2) . . . . ?
C3 C2 O1 C5 -0.1(2) . . . . ?
C1 C2 O1 C5 -177.7(2) . . . . ?
C4 C5 O1 C2 -0.8(2) . . . . ?
C6 C5 O1 C2 174.52(19) . . . . ?
O3 C1 O2 C11 60.7(2) . . . . ?
C2 C1 O2 C11 179.97(18) . . . . ?
C12 C11 O2 C1 -57.0(3) . . . . ?
O2 C1 O3 C13 -61.2(2) . . . . ?
C2 C1 O3 C13 -178.6(2) . . . . ?
C12 C13 O3 C1 58.4(2) . . . . ?
