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_7237809
_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, 0.5(C3 H7 N O)'
_chemical_formula_sum            'C23.5 H25.5 Cl2 N4.5 O4.5'
_chemical_formula_weight         513.88
_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     direct
_audit_creation_date             2019-02-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-02-28 deposited with the CCDC.	2019-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.013(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.7597(4)
_cell_length_b                   13.1892(3)
_cell_length_c                   25.4130(6)
_cell_measurement_reflns_used    9876
_cell_measurement_temperature    290.4(4)
_cell_measurement_theta_max      72.4000
_cell_measurement_theta_min      4.3880
_cell_volume                     4935.0(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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.4(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
  1 omega   19.00  103.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   57.0000 -180.0000 84

  2 omega   19.00  103.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   57.0000 -120.0000 84

  3 omega    0.00   26.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   94.0000 -131.4194 26

  4 omega  -31.00   53.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -57.0000   60.0000 84

  5 omega    1.00   75.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -99.0000    0.0000 74

  6 omega    1.00   75.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -99.0000 -120.0000 74

  7 omega  -31.00   53.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -57.0000   30.0000 84

  8 omega   38.00   91.00   1.0000    7.5800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

  9 omega   40.00   98.00   1.0000    7.5800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 58

 10 omega   87.00  178.00   1.0000    7.5800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -180.0000 91

 11 omega   38.00  116.00   1.0000    7.5800
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 78

 12 omega  100.00  178.00   1.0000    7.5800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 78

 13 omega   38.00   91.00   1.0000    7.5800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

 14 omega   38.00  116.00   1.0000    7.5800
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -60.0000 78

 15 omega   40.00   98.00   1.0000    7.5800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 58

 16 omega   38.00   91.00   1.0000    7.5800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

 17 omega   40.00  115.00   1.0000    7.5800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   90.0000 75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0068014000
_diffrn_orient_matrix_UB_12      0.1007488000
_diffrn_orient_matrix_UB_13      -0.0307235000
_diffrn_orient_matrix_UB_21      0.0101238000
_diffrn_orient_matrix_UB_22      -0.0581221000
_diffrn_orient_matrix_UB_23      -0.0519171000
_diffrn_orient_matrix_UB_31      -0.1037864000
_diffrn_orient_matrix_UB_32      -0.0122564000
_diffrn_orient_matrix_UB_33      -0.0072896000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            26531
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.666
_diffrn_reflns_theta_min         4.501
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.716
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39252
_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_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       block
_exptl_crystal_F_000             2144
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.3
_refine_diff_density_max         1.416
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     628
_refine_ls_number_reflns         9654
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0626
_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^)+(0.1216P)^2^+1.3263P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1735
_refine_ls_wR_factor_ref         0.1853
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8179
_reflns_number_total             9654
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9tc01337g2.cif
_cod_data_source_block           zxg-wm-2
_cod_original_formula_sum        'C23.50 H25.50 Cl2 N4.50 O4.50'
_cod_database_code               7237809
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Ternary CH refined with riding coordinates:
 C00U(H00U), C00W(H00W), C00Z(H00Z), C016(H016)
2.b Secondary CH2 refined with riding coordinates:
 C01I(H01A,H01D), C01K(H01E,H01F), C01O(H01T,H01U), C01R(H01V,H01W), C01S(H01G,
 H01I), C01T(H01X,H01Y), C01V(H01Z,HB), C01W(H01K,H01M)
2.c Aromatic/amide H refined with riding coordinates:
 N00D(H00D), N00G(H00G), N00I(H00I), N00J(H00J), C00T(H00T), C00V(H00V),
 C00X(H00X), C012(H012), C013(H013), C01A(H01O), C01B(H01B), C01C(H01C),
 C01E(H01Q), C01F(H01R), C01G(H01S), C01H(H01H), C01J(H01J), C01L(H01L),
 C01N(H01N), C01P(H01P), C01Q(H01)
2.d Idealised Me refined as rotating group:
 C01U(H0AA,H,HA), C01X(H1AA,HC,HD)
2.e Idealised tetrahedral OH refined as rotating group:
 O005(H005), O006(H006), O008(H008), O009(H009)
;
_olex2_submission_special_instructions 'No special instructions were received'