Photoswitchable hydrazones with pyridine-based rotors and halogen substituents
Kotásková, Lucie; Jewula, Pawel; Herchel, Radovan; Nemec, Ivan; Neugebauer, Petr; RSC Advances 14 (2024) 20856–20866; doi:10.1039/D4RA02909G

data_7248919
_publ_section_title
;
 Photoswitchable hydrazones with pyridine-based rotors and halogen
 substituents
;
_journal_issue                   29
_journal_name_full               'RSC Advances'
_journal_page_first              20856
_journal_page_last               20866
_journal_paper_doi               10.1039/D4RA02909G
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C15 H14 Br N3 O2'
_chemical_formula_sum            'C15 H14 Br N3 O2'
_chemical_formula_weight         348.201
_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_Int_Tables_number      14
_audit_creation_date             2023-11-10
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-02-25 deposited with the CCDC.	2024-06-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.166(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.7709(1)
_cell_length_b                   18.2539(5)
_cell_length_c                   16.7122(4)
_cell_measurement_reflns_used    6427
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      69.4440
_cell_measurement_theta_min      3.5880
_cell_volume                     1444.06(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.9761
_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    -63.00  21.00   0.50    0.70    --  -43.63  79.00 -28.00  168
  2  \w    -20.00  47.00   0.50    0.70    --   45.19 -79.00-153.00  134
  3  \w    -84.00 -27.00   0.50    3.50    --  -93.31  79.00 -28.00  114
  4  \w   -153.00-119.00   0.50    3.50    --  -93.31 -79.00-153.00   68
  5  \w    134.00 159.00   0.50    3.50    --   94.87  79.00 -28.00   50
  6  \w     32.00 101.00   0.50    3.50    --   94.87 -79.00-153.00  138
  7  \w    -16.00  16.00   0.50    0.70    --  -43.63  32.00 -30.00   64
  8  \w   -108.00 -64.00   0.50    0.70    --  -43.63-138.00 120.00   88
  9  \w    -22.00  23.00   0.50    0.70    --  -43.63  11.00  60.00   90
 10  \w    -23.00  19.00   0.50    0.70    --   45.19 -21.00 120.00   84
 11  \w      4.00  37.00   0.50    0.70    --   45.19 -32.00  60.00   66
 12  \w     64.00 112.00   0.50    0.70    --   45.19 138.00 150.00   96
 13  \w    -24.00  28.00   0.50    0.70    --   45.19 -21.00  30.00  104
 14  \w     -4.00  27.00   0.50    0.70    --   45.19-104.00 150.00   62
 15  \w     53.00  80.00   0.50    0.70    --   45.19-104.00 150.00   54
 16  \w    -15.00  15.00   0.50    0.70    --   45.19 -21.00-120.00   60
 17  \w     73.00  98.00   0.50    0.70    --   45.19 138.00 -90.00   50
 18  \w    -57.00 -32.00   0.50    3.50    --  -93.31  50.00-180.00   50
 19  \w    -61.00 -34.00   0.50    3.50    --  -93.31  59.00 150.00   54
 20  \w   -115.00 -26.00   0.50    3.50    --  -93.31 145.00  90.00  178
 21  \w    -57.00 -32.00   0.50    3.50    --  -93.31  50.00 -90.00   50
 22  \w    -68.00 -27.00   0.50    3.50    --  -93.31  59.00 -30.00   82
 23  \w   -128.00 -80.00   0.50    3.50    --  -93.31 -17.00  30.00   96
 24  \w    -56.00 -29.00   0.50    3.50    --  -93.31  50.00  90.00   54
 25  \w    -53.00 -27.00   0.50    3.50    --  -93.31  50.00 120.00   52
 26  \w   -148.00-100.00   0.50    3.50    --  -93.31 -42.00 -90.00   96
 27  \w   -161.00 -85.00   0.50    3.50    --  -93.31 -25.00-180.00  152
 28  \w     87.00 163.00   0.50    3.50    --   94.87  25.00 -60.00  152
 29  \w     29.00  54.00   0.50    3.50    --   94.87 -50.00-120.00   50
 30  \w    126.00 153.00   0.50    3.50    --   94.87  33.00  90.00   54
 31  \w     40.00  65.00   0.50    3.50    --   94.87 -59.00-120.00   50
 32  \w     30.00  83.00   0.50    3.50    --   94.87 -68.00  30.00  106
 33  \w     32.00  69.00   0.50    3.50    --   94.87 -59.00 -30.00   74
 34  \w     29.00  54.00   0.50    3.50    --   94.87 -50.00 -90.00   50
 35  \w     32.00  62.00   0.50    3.50    --   94.87 -59.00-150.00   60
 36  \w    -47.00 -22.00   0.50    0.70    --  -43.63  79.00 -28.00   50
 37  \w     29.00  54.00   0.50    5.50    --   94.87 -50.00   0.00   50
 38  \w    -67.00 -42.00   0.50    8.00    --  -95.95  58.00 110.00   50
 39  \w   -146.00-102.00   0.50    8.00    --  -95.95 -33.00  30.00   88
 40  \w    -63.00 -37.00   0.50    8.00    --  -95.95  77.00-150.00   52
 41  \w    -63.00 -37.00   0.50    8.00    --  -95.95  59.00  60.00   52
 42  \w   -106.00 -80.00   0.50    8.00    --  -95.95  77.00-150.00   52
 43  \w    138.00 163.00   0.50    8.00    --   97.51  33.00 120.00   50
 44  \w     90.00 128.00   0.50    8.00    --   97.51  33.00 120.00   76
 45  \w     85.00 147.00   0.50    8.00    --   97.51  42.00  30.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.9981
_diffrn_reflns_Laue_measured_fraction_max 0.9761
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10084
_diffrn_reflns_point_group_measured_fraction_full 0.9981
_diffrn_reflns_point_group_measured_fraction_max 0.9761
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         69.73
_diffrn_reflns_theta_min         3.60
_exptl_absorpt_coefficient_mu    3.957
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.57a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_description       needle
_exptl_crystal_F_000             703.370
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.7666
_refine_diff_density_min         -0.8299
_refine_diff_density_rms         0.0795
_refine_ls_d_res_high            0.8218
_refine_ls_d_res_low             12.2737
_refine_ls_goodness_of_fit_ref   1.0296
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     316
_refine_ls_number_reflns         2654
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0296
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0321
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0624P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0868
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              5
_reflns_limit_h_min              -5
_reflns_limit_k_max              22
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                2367
_reflns_number_total             2654
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4ra02909g2.cif
_cod_data_source_block           2-Brnosph
_cod_database_code               7248919
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
;
_olex2_refine_details
;
Refinement using NoSpherA2, an implementation of
NOn-SPHERical Atom-form-factors in Olex2.
Please cite:
F. Kleemiss et al. Chem. Sci. DOI 10.1039/D0SC05526C - 2021
NoSpherA2 implementation of HAR makes use of
tailor-made aspherical atomic form factors calculated
on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF
wavefunction - either Hartree-Fock or DFT using selected funtionals
 - for a fragment of the crystal.
This fragment can be embedded in an electrostatic crystal field by employing cluster charges
or modelled using implicit solvation models, depending on the software used.
The following options were used:
   SOFTWARE:       ORCA
   PARTITIONING:   NoSpherA2
   INT ACCURACY:   Normal
   METHOD:         B3LYP
   BASIS SET:      def2-TZVP
   CHARGE:         0
   MULTIPLICITY:   1
   DATE:           2023-11-10_22-52-59
;
_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
;