Studies of novel trifluoroacetylated diaryl hydrazone molecular photoswitches in solution and in the solid state
Accorsi, Gianluca; Capodilupo, Agostina-Lina; Claramunt, Rosa María; Clarkson, Guy J.; Farrán, A.; Gatti, Francesco G.; León, Salvador; Venturi, Silvia; New Journal of Chemistry 45 (2021) 12471–12478; doi:10.1039/D1NJ01677F

data_7060714
_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 H15 F3 N2 O'
_chemical_formula_sum            'C17 H15 F3 N2 O'
_chemical_formula_weight         320.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-26
_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                90
_cell_formula_units_Z            8
_cell_length_a                   8.14933(8)
_cell_length_b                   10.51816(9)
_cell_length_c                   36.3202(3)
_cell_measurement_reflns_used    17061
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.4110
_cell_measurement_theta_min      4.3340
_cell_volume                     3113.22(5)
_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_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -116.00 -17.00   1.00    1.00    --  -41.82 -37.00  90.00   99
  2  \w      1.00  83.00   1.00    1.00    --   41.82 -99.00-180.00   82
  3  \w     23.00  98.00   1.00    1.00    --   41.82-125.00 -30.00   75
  4  \w     81.00 178.00   1.00    3.13    --  107.00  45.00 -60.00   97
  5  \w     31.00 135.00   1.00    3.13    --  107.00 -30.00 120.00  104
  6  \w     35.00 136.00   1.00    3.13    --  107.00 -61.00 -30.00  101
  7  \w     81.00 178.00   1.00    3.13    --  107.00  45.00   0.00   97
  8  \w   -118.00  -9.00   1.00    1.00    --  -41.82 -77.00-120.00  109
  9  \w   -118.00  -9.00   1.00    1.00    --  -41.82 -77.00   0.00  109
 10  \w     81.00 178.00   1.00    3.13    --  107.00  45.00 120.00   97
 11  \w     79.00 178.00   1.00    3.13    --  107.00  30.00-150.00   99
 12  \w     24.00 110.00   1.00    3.13    --  107.00 -94.00 150.00   86
 13  \w     34.00 118.00   1.00    3.13    --  107.00-125.00 -30.00   84
 14  \w   -114.00 -14.00   1.00    1.00    --  -41.82 -57.00  60.00  100
 15  \w      1.00  83.00   1.00    1.00    --   41.82 -99.00  90.00   82
 16  \w     81.00 178.00   1.00    3.13    --  107.00  45.00  60.00   97
 17  \w     80.00 172.00   1.00    3.13    --  107.00  52.00-115.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1185151000
_diffrn_orient_matrix_UB_12      -0.0190898000
_diffrn_orient_matrix_UB_13      -0.0325715000
_diffrn_orient_matrix_UB_21      0.0178080000
_diffrn_orient_matrix_UB_22      -0.1452176000
_diffrn_orient_matrix_UB_23      0.0038614000
_diffrn_orient_matrix_UB_31      -0.1461803000
_diffrn_orient_matrix_UB_32      -0.0022333000
_diffrn_orient_matrix_UB_33      0.0268915000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            30520
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.649
_diffrn_reflns_theta_min         4.376
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.946
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85425
_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            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
The crystal chosen had racemic twinning. The ratio of the two possible chiral domains in the crystal 
refined to 0.84:0.16 using the TWIN and BASF commands in Shelxl.

;
_refine_ls_abs_structure_Flack   0.16(10)
_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     420
_refine_ls_number_reflns         6180
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0267
_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/[\s^2^(Fo^2^)+(0.0375P)^2^+0.3880P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0688
_refine_ls_wR_factor_ref         0.0697
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                5983
_reflns_number_total             6180
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj01677f2.cif
_cod_data_source_block           af9
_cod_depositor_comments
'Adding full bibliography for 7060712--7060714.cif.'
_cod_database_code               7060714
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H20 N2 O2 F3'
_shelx_estimated_absorpt_t_max   0.928
_shelx_estimated_absorpt_t_min   0.833
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_olex2_refinement_description
;

The NHs were located in a difference map but placed at a calculated position for the refinement.
1. Twinned data refinement
 Scales: 0.84(10)
 0.16(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 N105(H105), N205(H205), C211(H211), C113(H113), C210(H210), C213(H213),
 C117(H117), C217(H217), C208(H208), C111(H111), C108(H108), C110(H110),
 C114(H114), C116(H116), C214(H214), C216(H216), C215(H215), C115(H115)
3.b Idealised Me refined as rotating group:
 C27A(H27A,H27B,H27C), C17A(H17A,H17B,H17C), C29A(H29A,H29B,H29C), C19A(H19A,
 H19B,H19C)
;
_shelx_res_checksum              94178
_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 1.213
_oxdiff_exptl_absorpt_empirical_full_min 0.803