Salt–cocrystal continuum for photofunction modulation: stimuli-responsive fluorescence color-tuning of pyridine-modified intramolecular charge-transfer dyes and acid complexes
Yano, Yoshio; Ono, Toshikazu; Hatanaka, Sou; Gryko, Daniel T.; Hisaeda, Yoshio; Journal of Materials Chemistry C 7 (2019) 8847–; doi:10.1039/C9TC02524C

data_7237893
_publ_section_title
;
 Salt--cocrystal continuum for photofunction modulation:
 stimuli-responsive fluorescence color-tuning of pyridine-modified
 intramolecular charge-transfer dyes and acid complexes
;
_journal_issue                   29
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              8847
_journal_paper_doi               10.1039/C9TC02524C
_journal_volume                  7
_journal_year                    2019
_chemical_formula_moiety         '2(C H2 Cl2), 2(C7 H6 O2), C30 H24 N4'
_chemical_formula_sum            'C46 H40 Cl4 N4 O4'
_chemical_formula_weight         854.62
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-10-30
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.062(2)
_cell_length_b                   6.2048(7)
_cell_length_c                   27.631(3)
_cell_measurement_reflns_used    3355
_cell_measurement_temperature    123
_cell_measurement_theta_max      32.4190
_cell_measurement_theta_min      3.1630
_cell_volume                     4125.3(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_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_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -58.00 119.00   1.00  118.70    --   30.00  54.00 120.00  177
  2  \w      3.00  30.00   1.00  118.70    --   30.00  54.00   0.00   27
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0001478000
_diffrn_orient_matrix_UB_12      0.0016398000
_diffrn_orient_matrix_UB_13      0.0256876000
_diffrn_orient_matrix_UB_21      0.0294105000
_diffrn_orient_matrix_UB_22      -0.0064320000
_diffrn_orient_matrix_UB_23      -0.0001039000
_diffrn_orient_matrix_UB_31      0.0017268000
_diffrn_orient_matrix_UB_32      0.1140702000
_diffrn_orient_matrix_UB_33      -0.0004770000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            13766
_diffrn_reflns_point_group_measured_fraction_full 0.870
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.785
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.337
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.34a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       block
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          1.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details
;
 Flack x determined using 1976 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.47(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     530
_refine_ls_number_reflns         7325
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0732
_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^)+(0.1000P)^2^+4.8600P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1982
_refine_ls_wR_factor_ref         0.2046
_reflns_Friedel_coverage         0.703
_reflns_Friedel_fraction_full    0.735
_reflns_Friedel_fraction_max     0.733
_reflns_number_gt                6380
_reflns_number_total             7325
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9tc02524c11.cif
_cod_data_source_block           yano057
_cod_database_code               7237893
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     'PyPP-Benzoic acid'
_diffrn_oxdiff_ac3_digest_frames
;
0198425739f7e73604c35f8277da4f70af00204c6e2
;
_diffrn_oxdiff_ac3_digest_hkl
;
015c59a5edb5f5f5d899f6c2b6ec9e08cbfba1
;
_reflns_odcompleteness_completeness 99.79
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1B(H1BA,H1BB), C2B(H2BA,H2BB)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C3(H3), C13(H13), C8(H8), C16(H16), C11(H11), C28(H28), C29(H29),
 C6A(H6A), C15(H15), C10(H10), C22(H22), C14(H14), C6(H6), C18(H18), C25(H25),
 C3A(H3A), C19(H19), C9A(H9A), C2A(H2A), C12A(H12A), C26(H26), C13A(H13A),
 C21(H21), C5A(H5A), C4A(H4A), C10A(H10A), C11A(H11A)
2.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C23(H23A,H23B,H23C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1A(H1A)
;
_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 1.869
_oxdiff_exptl_absorpt_empirical_full_min 0.676