Structural insight into piezo-solvatochromism of Reichardt's dye.
Sobczak, Szymon; Katrusiak, Andrzej; IUCrJ 11 (2024) –; doi:10.1107/S2052252524004603

data_1571772
_publ_section_title
;
 Structural insight into piezo-solvatochromism of Reichardt's dye.
;
_journal_coeditor_code           LT5066
_journal_issue                   4
_journal_name_full               IUCrJ
_journal_paper_doi               10.1107/S2052252524004603
_journal_volume                  11
_journal_year                    2024
_chemical_formula_moiety         'C29 H21 N O, 6(O)'
_chemical_formula_sum            'C29 H21 N O7'
_chemical_formula_weight         495.47
_chemical_name_common
;
ET(1)*6H2O
;
_chemical_name_systematic
;
4-(2,4,6-triphenylpyridinium-1-yl)-phenolate hexahydrate
;
_chemical_properties_physical    Moisture-sensitive
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-02-15
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-02-20 deposited with the CCDC. 2024-02-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.311(4)
_cell_length_b                   23.948(6)
_cell_length_c                   7.27(2)
_cell_measurement_reflns_used    524
_cell_measurement_temperature    293.00
_cell_measurement_theta_max      26.372
_cell_measurement_theta_min      2.4680
_cell_volume                     2666(7)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.411
_diffrn_measured_fraction_theta_max 0.242
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2098
_diffrn_reflns_av_unetI/netI     0.2536
_diffrn_reflns_Laue_measured_fraction_full 0.411
_diffrn_reflns_Laue_measured_fraction_max 0.242
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       1
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            6172
_diffrn_reflns_point_group_measured_fraction_full 0.356
_diffrn_reflns_point_group_measured_fraction_max 0.194
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.325
_diffrn_reflns_theta_min         1.579
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_type   gaussian
_exptl_crystal_colour            'clear red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_preparation       solvatochromic
_exptl_crystal_recrystallization_method 'crystallized at high pressure'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 49 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   10.0(10)
_refine_ls_extinction_coef       0.18(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.276
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         526
_refine_ls_number_restraints     501
_refine_ls_restrained_S_all      0.929
_refine_ls_R_factor_all          0.2641
_refine_ls_R_factor_gt           0.1369
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3215
_refine_ls_wR_factor_ref         0.3781
_reflns_Friedel_coverage         0.395
_reflns_Friedel_fraction_full    0.267
_reflns_Friedel_fraction_max     0.128
_reflns_number_gt                242
_reflns_number_total             526
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lt5066.cif
_cod_data_source_block           et1_acetone_0_22gpa
_cod_original_cell_volume        2664(9)
_cod_database_code               1571772
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.981
_exptl_absorpt_special_details
;
Data were collected at room temperature (295(2) K) and pressure of 0.22(2) GPa
(220000 kPa).
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C17-O1
 1.3 with sigma of 0.06
 C7-C6 \\sim C6-C5 \\sim C5-C4 \\sim C15-C17 \\sim C15-C16 \\sim C16-C14 \\sim
C8-C13 \\sim C13-C12 \\sim C12-
 C11 \\sim C11-C10 \\sim C9-C10 \\sim C9-C8 \\sim C2-C1 \\sim C3-C2
 with sigma of 0.02
 C15-C15_$1 \\sim C16-C16_$1 \\sim C1-C1_$1 \\sim C2-C2_$1 \\sim C5-C5_$1 \\sim
C6-C6_$1
 with sigma of 0.02
3. Restrained planarity
 C5_$1, C6_$1, C4, C5, C6, C7
 with sigma of 0.1
 C1, C2, N1, C1_$1, C2_$1, C3
 with sigma of 0.1
4. Rigid bond restraints
 C4, C3, C5, C2, C6, C1, C7, N1, C8, C14, C9, C13, C16, C10, C12, C15, C11,
 C17, O1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
N1 \\sim C4 \\sim C3 \\sim C5 \\sim C2 \\sim C6 \\sim C1 \\sim C7 \\sim C8
\\sim C14 \\sim C9 \\sim C13 \\sim C16 \\sim C10 \\sim C12 \\sim C15 \\sim C11
\\sim C17 \\sim O1: within 2A with sigma of 0.04 and sigma for terminal atoms
of 0.08 within 2A
Uanis(N1) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C5) \\sim
Ueq, Uanis(C2) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C7)
\\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C9) \\sim Ueq,
Uanis(C13) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C12)
\\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C17) \\sim Ueq,
Uanis(O1) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C5) \\sim
Ueq, Uanis(C6) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of
0.02
6. Rigid body (RIGU) restrains
 C16, C4, C3, C5, C2, C6, C1, C7, N1, C8, C14, C9, C13, C10, C12, C15, C11,
 C17, O1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
7. Others
 Fixed Sof: O3W(0.5) O4W(0.5)
 Fixed X: C4(0)
 Fixed Z: C4(0.75)
8.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C13(H13), C12(H12), C11(H11), C10(H10), C9(H9), C5(H5), C6(H6),
 C7(H7), C16(H16), C15(H15)
8.b Fitted hexagon refined as free rotating group:
 C8(C13,C12,C11,C10,C9)
;
_shelx_res_checksum              53037
_shelx_hkl_checksum              93153
_olex2_submission_special_instructions 'No special instructions were received'