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_7248916
_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         348.20
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-02-25
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2024-02-25 deposited with the CCDC.	2024-06-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.171(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.77160(10)
_cell_length_b                   18.2538(5)
_cell_length_c                   16.7147(4)
_cell_measurement_reflns_used    6418
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      69.4500
_cell_measurement_theta_min      3.5870
_cell_volume                     1444.46(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 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.976
_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_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2730996000
_diffrn_orient_matrix_UB_12      -0.0445017000
_diffrn_orient_matrix_UB_13      -0.0023734000
_diffrn_orient_matrix_UB_21      -0.1316960000
_diffrn_orient_matrix_UB_22      -0.0374862000
_diffrn_orient_matrix_UB_23      -0.0783579000
_diffrn_orient_matrix_UB_31      0.1182584000
_diffrn_orient_matrix_UB_32      0.0610881000
_diffrn_orient_matrix_UB_33      -0.0498828000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.976
_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            10145
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.709
_diffrn_reflns_theta_min         3.601
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.956
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55858
_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            yellow
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.743
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2653
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0336
_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^)+(0.0653P)^2^+0.2676P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0945
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2398
_reflns_number_total             2653
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra02909g2.cif
_cod_data_source_block           2-Br
_cod_database_code               7248916
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     'LK Br switch'
_shelx_estimated_absorpt_t_max   0.827
_shelx_estimated_absorpt_t_min   0.301
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C4(H4), C3(H3), C8(H8), C11(H11), C9(H9), C10(H10), C2(H2A), C1(H1)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              36496
_shelx_hkl_checksum              46299
_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 1.677
_oxdiff_exptl_absorpt_empirical_full_min 0.517