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_7237808
_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
'0.67(C22 H22 Cl2 N4 O4), 0.33(C22 H21 Cl2 N4 O4), 0.17(C2 H6 O), 0.17(H2 O)'
_chemical_formula_sum            'C22.33 H23 Cl2 N4 O4.33'
_chemical_formula_weight         487.68
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-22
_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                91.331(2)
_cell_angle_beta                 97.757(2)
_cell_angle_gamma                93.114(3)
_cell_formula_units_Z            6
_cell_length_a                   10.6849(3)
_cell_length_b                   17.9849(6)
_cell_length_c                   20.2503(5)
_cell_measurement_reflns_used    13859
_cell_measurement_temperature    291.9(4)
_cell_measurement_theta_max      72.8180
_cell_measurement_theta_min      4.4160
_cell_volume                     3848.30(19)
_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      291.9(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 0.979
_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   -103.00 -19.00   1.00    1.04    --  -36.04 -57.00-150.00   84
  2  \w    -55.00  33.00   1.00    1.04    --  -36.04  38.00   0.00   88
  3  \w      9.00 104.00   1.00    1.04    --   36.04  77.00-180.00   95
  4  \w     17.00 105.00   1.00    1.04    --   36.04  38.00 -60.00   88
  5  \w     19.00 103.00   1.00    1.04    --   36.04  57.00  60.00   84
  6  \w    -31.00  53.00   1.00    1.04    --   36.04 -57.00 120.00   84
  7  \w      1.00  75.00   1.00    1.04    --   36.04 -99.00 -30.00   74
  8  \w     23.00  89.00   1.00    1.04    --   36.04-125.00-150.00   66
  9  \w      1.00  75.00   1.00    1.04    --   36.04 -99.00  90.00   74
 10  \w     39.00 115.00   1.00    4.16    --  108.71-111.00  90.00   76
 11  \w     40.00 126.00   1.00    4.16    --  108.71 -45.00  60.00   86
 12  \w     91.00 176.00   1.00    4.16    --  108.71  61.00   0.00   85
 13  \w     39.00 178.00   1.00    4.16    --  108.71   0.00  60.00  139
 14  \w     40.00 126.00   1.00    4.16    --  108.71 -45.00 150.00   86
 15  \w     40.00 126.00   1.00    4.16    --  108.71 -45.00 -90.00   86
 16  \w     42.00 127.00   1.00    4.16    --  108.71 -61.00   0.00   85
 17  \w     39.00 109.00   1.00    4.16    --  108.71 -94.00   0.00   70
 18  \w     39.00 130.00   1.00    4.16    --  108.71 -30.00   0.00   91
 19  \w     57.00 151.00   1.00    4.16    --  108.71 178.00   0.00   94
 20  \w     91.00 177.00   1.00    4.16    --  108.71  45.00  60.00   86
 21  \w     91.00 176.00   1.00    4.16    --  108.71  61.00  90.00   85
 22  \w     41.00 135.00   1.00    4.16    --  108.71 -77.00 120.00   94
 23  \w     39.00 109.00   1.00    4.16    --  108.71 -94.00-180.00   70
 24  \w     39.00 115.00   1.00    4.16    --  108.71-111.00 -30.00   76
 25  \w      9.00 104.00   1.00    1.04    --   36.04  77.00  90.00   95
;
_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      0.0538832000
_diffrn_orient_matrix_UB_12      0.0809907000
_diffrn_orient_matrix_UB_13      0.0131110000
_diffrn_orient_matrix_UB_21      0.1351320000
_diffrn_orient_matrix_UB_22      -0.0261923000
_diffrn_orient_matrix_UB_23      0.0010276000
_diffrn_orient_matrix_UB_31      -0.0090206000
_diffrn_orient_matrix_UB_32      0.0109839000
_diffrn_orient_matrix_UB_33      -0.0756811000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            40048
_diffrn_reflns_point_group_measured_fraction_full 0.675
_diffrn_reflns_point_group_measured_fraction_max 0.651
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.207
_diffrn_reflns_theta_min         4.183
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.574
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41093
_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    1.263
_exptl_crystal_description       block
_exptl_crystal_F_000             1522
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 4246 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1782
_refine_ls_number_reflns         20115
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0493
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0881P)^2^+0.3031P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1334
_refine_ls_wR_factor_ref         0.1391
_reflns_Friedel_coverage         0.331
_reflns_Friedel_fraction_full    0.350
_reflns_Friedel_fraction_max     0.324
_reflns_number_gt                18339
_reflns_number_total             20115
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9tc01337g2.cif
_cod_data_source_block           zxg-wm-5_sq
_cod_original_cell_volume        3848.3(2)
_cod_database_code               7237808
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.96
_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, All O(H,H) groups
2.a Free rotating group:
 O03D(H1AA,H)
2.b Ternary CH refined with riding coordinates:
 C021(H021), C025(H025), C02D(H02D), C02F(H02F), C02I(H02I), C02J(H02J),
 C02O(H02O), C02Q(H02Q), C02S(H02S), C035(H035), C042(H042), C04I(H04I)
2.c Secondary CH2 refined with riding coordinates:
 C038(H03F,H03G), C03B(H03O,H03R), C03E(H03H,H03J), C03F(H03A,H03B), C03G(H03T,
 H03U), C03N(H03C,H03D), C03O(H03Y,HA), C03T(H03K,H03L), C03V(H03M,H03N),
 C03W(H03,HB), C045(H04Z,HC), C048(H04J,H04K), C04K(H04A,H04B), C04P(H04T,H04U),
  C04R(H0AA,HD), C04U(H04V,H04W), C04V(H04F,H04H), C04W(H04C,H04D), C051(H05I,
 H05J), C052(H05A,H05B), C057(H05Q,H05R), C05A(H05K,H05L), C05D(H05D,H05E),
 C05H(H05O,H05P), C05K(H05F,H05G)
2.d Aromatic/amide H refined with riding coordinates:
 N00M(H00M), N00X(H00X), N013(H013), N014(H014), N016(H016), N017(H017),
 N01H(H01H), N01I(H01I), N01M(H01M), N01N(H01N), N027(H027), C02C(H02C),
 C02L(H02L), C02M(H02M), C02R(H02R), C02T(H02T), C02W(H02W), C02X(H02X),
 C02Y(H02Y), C02Z(H02Z), C03A(H03E), C03C(H03X), C03I(H03I), C03J(H03V),
 C03K(H03W), C03P(H03P), C03Q(H03Q), C03S(H03S), C03Z(H03Z), C040(H040),
 C044(H044), C046(H046), C047(H047), C049(H049), C04A(H04L), C04B(H04P),
 C04C(H04M), C04E(H04E), C04G(H04G), C04H(H04O), C04J(H04R), C04N(H04N),
 C04O(H04), C04Q(H04Q), C04S(H04S), C04X(H04X), C04Y(H04Y), C050(H050),
 C053(H053), C055(H055), C058(H058), C059(H059), C05B(H05M), C05C(H05C),
 C05E(H05S), C05F(H05H), C05G(H05N), C05I(H05T)
2.e Idealised Me refined as rotating group:
 C054(H05U,H05V,H05W)
2.f Idealised tetrahedral OH refined as rotating group:
 O00F(H00F), O00G(H00G), O00J(H00J), O00L(H00L), O00Q(H00Q), O00R(H00R),
 O00Y(H00Y), O010(H010), O011(H011), O019(H019), O01C(H01C), O01E(H01E),
 O01T(H01T)
;
_shelx_res_checksum              73744
_shelx_hkl_checksum              93267
_shelx_fab_checksum              40780
_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 2.158
_oxdiff_exptl_absorpt_empirical_full_min 0.675