Smart, chiral, and nonconjugated cyclohexane-based bis-salicylaldehyde hydrazides: multi-stimuli-responsive, turn-on, ratiometric, and thermochromic fluorescence, single-crystal structures via DFT calculations
Wang, Man; Cheng, Caiqi; Li, Chunbo; Wu, Dehua; Song, Jintong; Wang, Jun; Zhou, Xiangge; Xiang, Haifeng; Liu, Jin; Journal of Materials Chemistry C 7 (2019) 6767–; doi:10.1039/C9TC01337G

data_7237806
_publ_section_title
;
 Smart, chiral, and nonconjugated cyclohexane-based bis-salicylaldehyde
 hydrazides: multi-stimuli-responsive, turn-on, ratiometric, and
 thermochromic fluorescence, single-crystal structures via DFT
 calculations
;
_journal_issue                   22
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              6767
_journal_paper_doi               10.1039/C9TC01337G
_journal_volume                  7
_journal_year                    2019
_chemical_formula_moiety         'C22 H22 Cl2 N4 O4, C2 H6 O S, O2 S'
_chemical_formula_sum            'C24 H28 Cl2 N4 O7 S2'
_chemical_formula_weight         619.52
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-07-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-05 deposited with the CCDC.	2019-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                95.790(6)
_cell_angle_beta                 104.335(6)
_cell_angle_gamma                114.902(8)
_cell_formula_units_Z            2
_cell_length_a                   10.7942(8)
_cell_length_b                   11.0971(9)
_cell_length_c                   15.1654(9)
_cell_measurement_reflns_used    3161
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.2470
_cell_measurement_theta_min      3.7090
_cell_volume                     1552.3(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.836
_diffrn_measurement_details
;
  1 omega   -4.00   22.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669   19.0000   90.0000 26

  2 omega  -41.00   49.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669   77.0000   30.0000 90

  3 omega  -43.00  -17.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669   19.0000   90.0000 26

  4 omega  -14.00   20.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000  150.0000 34

  5 omega  -83.00   12.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -77.0000  -90.0000 95

  6 omega   58.00   84.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       16.8419   57.0000 -180.0000 26

  7 omega   -1.00   80.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       16.8419   38.0000 -180.0000 81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0192654000
_diffrn_orient_matrix_UB_12      0.0531525000
_diffrn_orient_matrix_UB_13      0.0066861000
_diffrn_orient_matrix_UB_21      0.0166645000
_diffrn_orient_matrix_UB_22      0.0023963000
_diffrn_orient_matrix_UB_23      0.0486217000
_diffrn_orient_matrix_UB_31      0.0721423000
_diffrn_orient_matrix_UB_32      0.0492056000
_diffrn_orient_matrix_UB_33      0.0074783000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.836
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13646
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.401
_diffrn_reflns_theta_min         2.979
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.389
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             644
_refine_diff_density_max         2.008
_refine_diff_density_min         -0.717
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.381
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         7165
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.381
_refine_ls_R_factor_all          0.1539
_refine_ls_R_factor_gt           0.1115
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3510
_refine_ls_wR_factor_ref         0.3966
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4389
_reflns_number_total             7165
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9tc01337g2.cif
_cod_data_source_block           180710_s2_wm
_cod_database_code               7237806
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2o3cl1
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uiso(S37) = Uiso(S37A)
Uiso(O26) = Uiso(O3A)
3. Others
 Sof(S37A)=Sof(O3A)=1-FVAR(1)
 Sof(S37)=Sof(O26)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10)
4.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
4.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), C4(H4A), C5(H5), C6(H6), C7(H7), C16(H16), C20(H20), C21(H21),
  C22(H22)
4.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
4.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_shelx_res_checksum              11331
_shelx_hkl_checksum              27241
_olex2_submission_special_instructions 'No special instructions were received'