#------------------------------------------------------------------------------
#$Date: 2021-09-06 14:58:37 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268841 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/07/7060712.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_7060712
loop_
_publ_author_name
'Accorsi, Gianluca'
'Capodilupo, Agostina-Lina'
'Claramunt, Rosa María'
'Clarkson, Guy J.'
'Farrán, A.'
'Gatti, Francesco G.'
'León, Salvador'
'Venturi, Silvia'
_publ_section_title
;
 Studies of novel trifluoroacetylated diaryl hydrazone molecular
 photoswitches in solution and in the solid state
;
_journal_issue                   28
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              12471
_journal_page_last               12478
_journal_paper_doi               10.1039/D1NJ01677F
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C17 H9 F9 N2 O'
_chemical_formula_sum            'C17 H9 F9 N2 O'
_chemical_formula_weight         428.26
_space_group_crystal_system      trigonal
_space_group_IT_number           147
_space_group_name_Hall           '-P 3'
_space_group_name_H-M_alt        'P -3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-29 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   19.50530(10)
_cell_length_b                   19.50530(10)
_cell_length_c                   7.90760(10)
_cell_measurement_reflns_used    15568
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      77.7840
_cell_measurement_theta_min      4.5120
_cell_volume                     2605.44(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1417
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -92.00   3.00   1.00    4.00    --  -41.46 125.00-150.00   95
  2  ω    -50.00  33.00   1.00    4.00    --  -41.46  38.00   0.00   83
  3  ω    -33.00  66.00   1.00    4.00    --   41.46 -38.00-150.00   99
  4  ω     41.00  98.00   1.00   16.00    --  114.00 -45.00 -60.00   57
  5  ω     38.00  91.00   1.00   16.00    --  114.00 -30.00 -60.00   53
  6  ω     41.00  98.00   1.00   16.00    --  114.00 -45.00  90.00   57
  7  ω     38.00  91.00   1.00   16.00    --  114.00 -30.00   0.00   53
  8  ω     41.00  98.00   1.00   16.00    --  114.00 -45.00 150.00   57
  9  ω     32.00 167.00   1.00   16.00    --  114.00 -15.00 -90.00  135
 10  ω    100.00 178.00   1.00   16.00    --  114.00 111.00-120.00   78
 11  ω     41.00  98.00   1.00   16.00    --  114.00 -45.00-120.00   57
 12  ω     32.00 167.00   1.00   16.00    --  114.00 -15.00  90.00  135
 13  ω   -114.00 -13.00   1.00    4.00    --  -41.46 -57.00-180.00  101
 14  ω   -114.00 -14.00   1.00    4.00    --  -41.46 -52.00 -68.00  100
 15  ω     38.00 113.00   1.00   16.00    --  114.00-111.00 -60.00   75
 16  ω     61.00 178.00   1.00   16.00    --  114.00  15.00   0.00  117
 17  ω     38.00 113.00   1.00   16.00    --  114.00-111.00  90.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0613723000
_diffrn_orient_matrix_UB_12      -0.0001766000
_diffrn_orient_matrix_UB_13      -0.1229405000
_diffrn_orient_matrix_UB_21      -0.0423757000
_diffrn_orient_matrix_UB_22      -0.0910065000
_diffrn_orient_matrix_UB_23      -0.0088498000
_diffrn_orient_matrix_UB_31      -0.0524651000
_diffrn_orient_matrix_UB_32      -0.0054726000
_diffrn_orient_matrix_UB_33      0.1509438000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            22438
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.968
_diffrn_reflns_theta_min         4.534
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.535
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69487
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_description       block
_exptl_crystal_F_000             1284
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3692
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0332
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0454P)²+0.8474P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0910
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3548
_reflns_number_total             3692
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj01677f2.cif
_cod_data_source_block           af15
_cod_depositor_comments
'Adding full bibliography for 7060712--7060714.cif.'
_cod_database_code               7060712
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H20 N2 O2 F3'
_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_estimated_absorpt_t_max   0.749
_shelx_estimated_absorpt_t_min   0.552
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.08
_olex2_refinement_description
;
The NH was located in a difference map but refined with restraints
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N8(H8), C3(H3), C18(H18), C6(H6), C14(H14), C5(H5), C17(H17), C15(H15),
 C16(H16)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.411
_oxdiff_exptl_absorpt_empirical_full_min 0.843
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
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
F4A F 0.74744(4) 0.59879(5) 0.93385(10) 0.03725(19) Uani 1 1 d . . . . .
F12A F 0.31106(5) 0.52825(5) 0.51860(11) 0.0424(2) Uani 1 1 d . . . . .
F12B F 0.30218(5) 0.53581(5) 0.78939(11) 0.0437(2) Uani 1 1 d . . . . .
F1B F 0.44406(6) 0.31217(5) 0.98151(11) 0.0483(2) Uani 1 1 d . . . . .
F4B F 0.75212(5) 0.64181(6) 0.68357(11) 0.0482(2) Uani 1 1 d . . . . .
F1C F 0.45286(6) 0.29120(5) 0.72042(11) 0.0456(2) Uani 1 1 d . . . . .
F12C F 0.20974(5) 0.52727(5) 0.62800(14) 0.0503(2) Uani 1 1 d . . . . .
F4C F 0.71653(5) 0.68834(5) 0.89014(14) 0.0520(2) Uani 1 1 d . . . . .
F1A F 0.55268(6) 0.32618(5) 0.88213(15) 0.0569(3) Uani 1 1 d . . . . .
O11 O 0.14471(5) 0.37582(6) 0.64120(13) 0.0381(2) Uani 1 1 d . . . . .
N9 N 0.33674(6) 0.41812(6) 0.70228(12) 0.0268(2) Uani 1 1 d . . . . .
N8 N 0.38606(6) 0.39124(6) 0.73538(13) 0.0289(2) Uani 1 1 d . . . . .
H8 H 0.368620 0.340185 0.744921 0.035 Uiso 1 1 calc R . . . .
C10 C 0.26134(7) 0.36976(7) 0.69061(14) 0.0265(2) Uani 1 1 d . . . . .
C3 C 0.59944(7) 0.48078(7) 0.83449(15) 0.0277(2) Uani 1 1 d . . . . .
H3 H 0.635783 0.465474 0.874322 0.033 Uiso 1 1 calc R . . . .
C4 C 0.62522(7) 0.55961(7) 0.80006(14) 0.0262(2) Uani 1 1 d . . . . .
C18 C 0.24272(7) 0.23795(7) 0.60723(16) 0.0311(3) Uani 1 1 d . . . . .
H18 H 0.287233 0.264325 0.534508 0.037 Uiso 1 1 calc R . . . .
C7 C 0.46638(7) 0.44667(7) 0.75450(15) 0.0259(2) Uani 1 1 d . . . . .
C13 C 0.21866(7) 0.28193(7) 0.70421(15) 0.0270(2) Uani 1 1 d . . . . .
C2 C 0.52037(7) 0.42409(7) 0.81073(15) 0.0269(2) Uani 1 1 d . . . . .
C6 C 0.49372(7) 0.52622(7) 0.71611(16) 0.0294(2) Uani 1 1 d . . . . .
H6 H 0.457940 0.541862 0.674319 0.035 Uiso 1 1 calc R . . . .
C4A C 0.70976(7) 0.62174(7) 0.82661(16) 0.0300(3) Uani 1 1 d . . . . .
C14 C 0.15335(7) 0.24266(8) 0.81094(16) 0.0332(3) Uani 1 1 d . . . . .
H14 H 0.136506 0.272029 0.877646 0.040 Uiso 1 1 calc R . . . .
C11 C 0.21563(7) 0.41000(7) 0.65967(15) 0.0293(2) Uani 1 1 d . . . . .
C5 C 0.57240(7) 0.58202(7) 0.73869(16) 0.0285(2) Uani 1 1 d . . . . .
H5 H 0.590622 0.635946 0.712268 0.034 Uiso 1 1 calc R . . . .
C1 C 0.49362(8) 0.33898(7) 0.84944(17) 0.0318(3) Uani 1 1 d . . . . .
C12 C 0.26121(8) 0.50204(8) 0.64924(18) 0.0346(3) Uani 1 1 d . . . . .
C17 C 0.20197(9) 0.15583(8) 0.61640(19) 0.0396(3) Uani 1 1 d . . . . .
H17 H 0.218679 0.126149 0.550375 0.047 Uiso 1 1 calc R . . . .
C15 C 0.11310(8) 0.16073(9) 0.81947(18) 0.0410(3) Uani 1 1 d . . . . .
H15 H 0.068817 0.134093 0.892694 0.049 Uiso 1 1 calc R . . . .
C16 C 0.13697(9) 0.11735(8) 0.7220(2) 0.0442(3) Uani 1 1 d . . . . .
H16 H 0.108703 0.061171 0.727598 0.053 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C10 N9 N8 120.57(10) . . ?
N9 N8 H8 121.1 . . ?
N9 N8 C7 117.89(10) . . ?
C7 N8 H8 121.1 . . ?
N9 C10 C13 127.73(11) . . ?
N9 C10 C11 113.18(10) . . ?
C11 C10 C13 119.09(10) . . ?
C4 C3 H3 120.0 . . ?
C4 C3 C2 119.95(10) . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C4A 120.90(10) . . ?
C3 C4 C5 120.14(11) . . ?
C5 C4 C4A 118.95(11) . . ?
C13 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C13 120.39(12) . . ?
N8 C7 C2 121.27(10) . . ?
N8 C7 C6 119.54(10) . . ?
C6 C7 C2 119.19(11) . . ?
C18 C13 C10 120.11(11) . . ?
C14 C13 C10 120.51(11) . . ?
C14 C13 C18 119.37(11) . . ?
C3 C2 C7 120.14(11) . . ?
C3 C2 C1 119.08(10) . . ?
C7 C2 C1 120.77(11) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 C7 120.28(11) . . ?
C5 C6 H6 119.9 . . ?
F4A C4A F4B 105.75(10) . . ?
F4A C4A C4 112.70(10) . . ?
F4B C4A C4 112.82(10) . . ?
F4C C4A F4A 106.46(10) . . ?
F4C C4A F4B 106.67(11) . . ?
F4C C4A C4 111.95(10) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.86(12) . . ?
C15 C14 H14 120.1 . . ?
O11 C11 C10 123.88(11) . . ?
O11 C11 C12 117.80(11) . . ?
C10 C11 C12 118.31(10) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.24(11) . . ?
C6 C5 H5 119.9 . . ?
F1B C1 F1C 105.09(11) . . ?
F1B C1 C2 112.00(10) . . ?
F1C C1 C2 111.74(10) . . ?
F1A C1 F1B 107.53(11) . . ?
F1A C1 F1C 106.71(11) . . ?
F1A C1 C2 113.27(11) . . ?
F12A C12 C11 111.70(10) . . ?
F12B C12 F12A 108.24(11) . . ?
F12B C12 C11 112.43(11) . . ?
F12C C12 F12A 107.51(11) . . ?
F12C C12 F12B 107.40(11) . . ?
F12C C12 C11 109.36(10) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 C18 119.84(13) . . ?
C16 C17 H17 120.1 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.49(13) . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C15 120.04(13) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
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
F4A C4A 1.3376(14) . ?
F12A C12 1.3329(16) . ?
F12B C12 1.3320(16) . ?
F1B C1 1.3391(16) . ?
F4B C4A 1.3386(15) . ?
F1C C1 1.3419(15) . ?
F12C C12 1.3314(15) . ?
F4C C4A 1.3363(15) . ?
F1A C1 1.3205(15) . ?
O11 C11 1.2071(15) . ?
N9 N8 1.3316(14) . ?
N9 C10 1.2939(15) . ?
N8 H8 0.8800 . ?
N8 C7 1.3972(15) . ?
C10 C13 1.4877(16) . ?
C10 C11 1.4732(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.3850(17) . ?
C3 C2 1.3897(17) . ?
C4 C4A 1.4945(16) . ?
C4 C5 1.3923(16) . ?
C18 H18 0.9500 . ?
C18 C13 1.3953(17) . ?
C18 C17 1.3891(18) . ?
C7 C2 1.4017(16) . ?
C7 C6 1.3988(16) . ?
C13 C14 1.3950(17) . ?
C2 C1 1.5018(16) . ?
C6 H6 0.9500 . ?
C6 C5 1.3788(17) . ?
C14 H14 0.9500 . ?
C14 C15 1.3858(19) . ?
C11 C12 1.5570(17) . ?
C5 H5 0.9500 . ?
C17 H17 0.9500 . ?
C17 C16 1.384(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(2) . ?
C16 H16 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N8 H8 F1B 0.88 2.60 3.0317(14) 111.1 . yes
N8 H8 F1C 0.88 2.28 2.8393(13) 120.9 . yes
