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_7248917
_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 I N3 O2'
_chemical_formula_sum            'C15 H14 I N3 O2'
_chemical_formula_weight         395.19
_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             2023-10-18
_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                 95.506(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.6839(2)
_cell_length_b                   18.5687(8)
_cell_length_c                   16.9966(6)
_cell_measurement_reflns_used    4465
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      69.3040
_cell_measurement_theta_min      3.4770
_cell_volume                     1471.44(10)
_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 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.984
_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    -34.00  23.00   0.50    2.00    --  -43.25  81.00  14.00  114
  2  \w     -9.00  28.00   0.50    2.00    --   44.82 -81.00-108.00   74
  3  \w   -120.00 -94.00   0.50    6.00    --  -95.95  81.00  14.00   52
  4  \w   -151.00 -78.00   0.50    6.00    --  -95.95 -81.00-108.00  146
  5  \w     52.00  78.00   0.50    6.00    --   97.51 -81.00-108.00   52
  6  \w    122.00 147.00   0.50    6.00    --   97.51  81.00  14.00   50
  7  \w   -108.00 -28.00   0.50    2.00    --  -43.25 -54.00  90.00  160
  8  \w    -99.00 -74.00   0.50    2.00    --  -43.25-138.00   0.00   50
  9  \w    -19.00  22.00   0.50    2.00    --  -43.25  11.00  30.00   82
 10  \w   -108.00 -73.00   0.50    2.00    --  -43.25-138.00-150.00   70
 11  \w    -78.00 -49.00   0.50    2.00    --  -43.25 -32.00 -90.00   58
 12  \w   -108.00 -83.00   0.50    2.00    --  -43.25 -32.00 -90.00   50
 13  \w     -5.00  34.00   0.50    2.00    --   44.82 -32.00-120.00   78
 14  \w    -13.00  14.00   0.50    2.00    --   44.82 -21.00-180.00   54
 15  \w    -14.00  35.00   0.50    2.00    --   44.82 -32.00   0.00   98
 16  \w    -81.00 -51.00   0.50    6.00    --  -95.95  68.00  90.00   60
 17  \w   -163.00 -88.00   0.50    6.00    --  -95.95 -25.00-180.00  150
 18  \w   -118.00 -81.00   0.50    6.00    --  -95.95-117.00 -30.00   74
 19  \w    -88.00 -38.00   0.50    6.00    --  -95.95  81.00  14.00  100
 20  \w    -68.00 -32.00   0.50    6.00    --  -95.95  59.00   0.00   72
 21  \w   -106.00 -45.00   0.50    6.00    --  -95.95  96.00 120.00  122
 22  \w   -158.00 -79.00   0.50    6.00    --  -95.95 -86.00 -30.00  158
 23  \w   -161.00-126.00   0.50    6.00    --  -95.95-117.00 -30.00   70
 24  \w   -151.00-101.00   0.50    6.00    --  -95.95 -96.00 -60.00  100
 25  \w     31.00  56.00   0.50    6.00    --   97.51 -59.00-150.00   50
 26  \w     55.00  82.00   0.50    6.00    --   97.51 -68.00-120.00   54
 27  \w     31.00  56.00   0.50    6.00    --   97.51 -50.00 150.00   50
 28  \w     31.00  56.00   0.50    6.00    --   97.51 -50.00 -30.00   50
 29  \w     31.00  57.00   0.50    6.00    --   97.51 -50.00  90.00   52
 30  \w     81.00 163.00   0.50    6.00    --   97.51  50.00  60.00  164
 31  \w     31.00  56.00   0.50    6.00    --   97.51 -50.00-120.00   50
 32  \w     34.00  59.00   0.50    6.00    --   97.51 -68.00  30.00   50
 33  \w     34.00  63.00   0.50    6.00    --   97.51 -59.00 -90.00   58
;
_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      0.1091821000
_diffrn_orient_matrix_UB_12      -0.0490319000
_diffrn_orient_matrix_UB_13      -0.0637898000
_diffrn_orient_matrix_UB_21      -0.1208190000
_diffrn_orient_matrix_UB_22      0.0529245000
_diffrn_orient_matrix_UB_23      -0.0646209000
_diffrn_orient_matrix_UB_31      0.2874846000
_diffrn_orient_matrix_UB_32      0.0409427000
_diffrn_orient_matrix_UB_33      0.0071153000
_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  0.0441
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7046
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.574
_diffrn_reflns_theta_min         3.534
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    17.176
_exptl_absorpt_correction_T_max  0.396
_exptl_absorpt_correction_T_min  0.119
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.57a (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.784
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.217
_refine_diff_density_min         -2.092
_refine_diff_density_rms         0.197
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2730
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0550
_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^)+(0.1215P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1458
_refine_ls_wR_factor_ref         0.1492
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2461
_reflns_number_total             2730
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra02909g2.cif
_cod_data_source_block           2-I
_cod_database_code               7248917
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C60  H56  I4  N12  O8  '
_shelx_estimated_absorpt_t_max   0.340
_shelx_estimated_absorpt_t_min   0.086
_reflns_odcompleteness_completeness 99.00
_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:
 N3(H3), C10(H10), C8(H8), C6(H6), C5(H5), C9(H9), C3(H3A), C4(H4), C7(H7)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              93900
_shelx_hkl_checksum              51198
_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 2.076
_oxdiff_exptl_absorpt_empirical_full_min 0.466