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_7237804
_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_absolute_configuration ad
_chemical_formula_moiety         'C22 H22 Cl2 N4 O4, 2(C3 H7 N O)'
_chemical_formula_sum            'C28 H36 Cl2 N6 O6'
_chemical_formula_weight         623.53
_space_group_crystal_system      trigonal
_space_group_IT_number           145
_space_group_name_Hall           'P 32'
_space_group_name_H-M_alt        'P 32'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-12-05
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2019-01-05 deposited with the CCDC.	2019-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   10.6600(3)
_cell_length_b                   10.6600(3)
_cell_length_c                   24.2225(6)
_cell_measurement_reflns_used    3310
_cell_measurement_temperature    295.84(16)
_cell_measurement_theta_max      71.0250
_cell_measurement_theta_min      3.6970
_cell_volume                     2383.77(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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      295.84(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_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    -53.00  31.00   1.00    1.00    --  -36.17  57.00 150.00   84
  2  \w    -33.00 105.00   1.00    1.00    --   36.17   0.00 120.00  138
  3  \w     39.00 109.00   1.00    2.53    --  108.71 -94.00  90.00   70
  4  \w     41.00 135.00   1.00    2.53    --  108.71 -77.00  30.00   94
  5  \w     91.00 176.00   1.00    2.53    --  108.71  61.00-180.00   85
  6  \w     42.00 127.00   1.00    2.53    --  108.71 -61.00  60.00   85
  7  \w     91.00 176.00   1.00    2.53    --  108.71  61.00-145.00   85
  8  \w      1.00  75.00   1.00    1.00    --   36.17 -99.00   0.00   74
  9  \w     19.00 103.00   1.00    1.00    --   36.17  57.00-180.00   84
;
_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_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0997397000
_diffrn_orient_matrix_UB_12      -0.0121928000
_diffrn_orient_matrix_UB_13      0.0431037000
_diffrn_orient_matrix_UB_21      -0.0672290000
_diffrn_orient_matrix_UB_22      -0.1623344000
_diffrn_orient_matrix_UB_23      -0.0133438000
_diffrn_orient_matrix_UB_31      0.1156970000
_diffrn_orient_matrix_UB_32      0.0365807000
_diffrn_orient_matrix_UB_33      -0.0448406000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            8846
_diffrn_reflns_point_group_measured_fraction_full 0.731
_diffrn_reflns_point_group_measured_fraction_max 0.705
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.980
_diffrn_reflns_theta_min         4.790
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.251
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       irregular
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details
;
 Flack x determined using 1117 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.030(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         4469
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0620
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1182P)^2^+0.1995P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1633
_refine_ls_wR_factor_ref         0.1709
_reflns_Friedel_coverage         0.437
_reflns_Friedel_fraction_full    0.463
_reflns_Friedel_fraction_max     0.428
_reflns_number_gt                4047
_reflns_number_total             4469
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9tc01337g2.cif
_cod_data_source_block           zxg-wm
_cod_original_cell_volume        2383.78(13)
_cod_database_code               7237804
_reflns_odcompleteness_completeness 99.97
_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:
 C00I(H00I), C00L(H00L)
2.b Secondary CH2 refined with riding coordinates:
 C00N(H00A,H00B), C00R(H00C,H00E), C00T(H00F,H00H), C00Y(H00J,H00K)
2.c Aromatic/amide H refined with riding coordinates:
 N006(H006), N00D(H00D), C00G(H00G), C00O(H00O), C00Q(H00Q), C00S(H00S),
 C00V(H00V), C00X(H00X), C010(H010), C011(H011), C012(H012), C013(H013)
2.d Idealised Me refined as rotating group:
 C00Z(H00M,H00N,H00P), C014(H01D,H01E,H01F), C015(H01A,H01B,H01C), C016(H01G,
 H01H,H01I)
2.e Idealised tetrahedral OH refined as rotating group:
 O004(H004), O005(H005)
;
_shelx_res_checksum              52114
_shelx_hkl_checksum              54071
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2018-12-04
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.836
_oxdiff_exptl_absorpt_empirical_full_min 0.722