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

data_1571776
_publ_section_title
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 Structural insight into piezo-solvatochromism of Reichardt's dye.
;
_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, 4(C2 H6 O), O'
_chemical_formula_sum            'C37 H45 N O6'
_chemical_formula_weight         599.74
_chemical_name_common
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ET(1)*4C2H5OH*H2O
;
_chemical_name_systematic
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4-(2,4,6-triphenylpyridinium-1-yl)-phenolate ethanol solvate
;
_chemical_properties_physical    Moisture-sensitive
_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_Hall           'R 3 -2"c'
_space_group_name_H-M_alt        'R 3 c :H'
_atom_sites_solution_hydrogens   mixed
_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                120
_cell_formula_units_Z            18
_cell_length_a                   23.645(8)
_cell_length_b                   23.645(8)
_cell_length_c                   30.91(2)
_cell_measurement_reflns_used    654
_cell_measurement_temperature    293.00
_cell_measurement_theta_max      26.372
_cell_measurement_theta_min      2.4680
_cell_volume                     14966(12)
_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 0.778
_diffrn_measured_fraction_theta_max 0.363
_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  0.2296
_diffrn_reflns_av_unetI/netI     0.5157
_diffrn_reflns_Laue_measured_fraction_full 0.778
_diffrn_reflns_Laue_measured_fraction_max 0.363
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5030
_diffrn_reflns_point_group_measured_fraction_full 0.731
_diffrn_reflns_point_group_measured_fraction_max 0.294
_diffrn_reflns_theta_full        25.400
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.303
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_description       block
_exptl_crystal_F_000             5796
_exptl_crystal_preparation       'crystallized in DAC,solvatochromic'
_exptl_crystal_recrystallization_method 'crystallized at high pressure'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 125 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -5.4(10)
_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   0.952
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         2002
_refine_ls_number_restraints     462
_refine_ls_restrained_S_all      0.873
_refine_ls_R_factor_all          0.3771
_refine_ls_R_factor_gt           0.1248
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1651P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2723
_refine_ls_wR_factor_ref         0.4036
_reflns_Friedel_coverage         0.612
_reflns_Friedel_fraction_full    0.684
_reflns_Friedel_fraction_max     0.223
_reflns_number_gt                504
_reflns_number_total             2002
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lt5066.cif
_cod_data_source_block           et1_ethanol_0_76gpa
_cod_original_cell_volume        14968(16)
_cod_original_sg_symbol_H-M      'R 3 c'
_cod_database_code               1571776
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.969
_exptl_absorpt_special_details
;
Data were collected at room temperature (295(2) K) and pressure of 0.76(2) GPa
(760000 kPa).
;
_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. Restrained distances
 O1-H2E_$1
 1.85 with sigma of 0.05
 H4E_$2-O1
 1.9 with sigma of 0.1
 H2E-O2E
 0.89 with sigma of 0.005
 O2E-H1E
 1.9 with sigma of 0.02
 H4E-O4E
 0.89 with sigma of 0.01
 O4E-H4E
 0.89 with sigma of 0.01
 H4E-C8E
 1.8 with sigma of 0.02
 H3E-O4E
 1.9 with sigma of 0.05
 O4E-C8E \\sim O3E-C6E \\sim O2E-C3E \\sim O1E-C2E
 with sigma of 0.02
 C8'-C1' \\sim C4-C3 \\sim C8-C1
 with sigma of 0.02
 O4E-C7E \\sim O3E-C5E \\sim O2E-C4E \\sim O1E-C1E
 with sigma of 0.02
 C7-C2 \\sim C7-C2'
 with sigma of 0.02
 C17-C1 \\sim C17-C1'
 with sigma of 0.02
 C14-C1' \\sim C14-C1
 with sigma of 0.02
 C4-C2' \\sim C4-C2
 with sigma of 0.02
 C2E-C1E \\sim C4E-C3E \\sim C6E-C5E \\sim C8E-C7E
 with sigma of 0.02
 O1-C16' \\sim O1-C16
 with sigma of 0.02
 C2'-C1' \\sim C3-C2' \\sim C3-C2 \\sim C2-C1
 with sigma of 0.02
 N1-C1 \\sim N1-C1'
 with sigma of 0.02
3. Restrained planarity
 C5, H5, C4, C5', H5', C6', H6', C7, H7, C6, H6, C3
 with sigma of 0.1
4. Rigid bond restraints
 C4E, C3E, O2E
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C7E, C8E, O4E
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C5E, C6E, O3E
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C1E, C2E, O1E
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C5, C4, C5', C6', C6, C7
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
O2E \\sim C3E \\sim C4E: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
O4E \\sim C8E \\sim C7E: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
C5E \\sim C6E \\sim O3E: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
O1E \\sim C2E \\sim C1E: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
C5' \\sim C6 \\sim C7 \\sim C4 \\sim C6' \\sim C5: within 2A with sigma of 0.04
and sigma for terminal atoms of 0.08 within 2A
Uanis(O2E) \\sim Ueq, Uanis(C6E) \\sim Ueq, Uanis(C2') \\sim Ueq, Uanis(C7)
\\sim Ueq, Uanis(C8') \\sim Ueq, Uanis(C13') \\sim Ueq, Uanis(C5E) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C10') \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O4E) \\sim Ueq, Uanis(C8E) \\sim Ueq, Uanis(C7E) \\sim Ueq: with sigma of
0.02 and sigma for terminal atoms of 0.04
6. Rigid body (RIGU) restrains
 C13, C3, C2, C2', C4, C1, C1', C5, C5', N1, C8, C8', C6, C6', C14, C9, C13',
 C9', C7, C15', C15, C12, C10, C12', C10', C16', C16, C11, C11', C17, O1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O4E, C8E, C7E
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C4E, C3E, O2E
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O2E, C3E, C4E
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C8E, C7E, O4E
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1E, O1E, C2E
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C2E, O1E, C1E
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O3E, C6E, C5E
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
7. Others
 Fixed Sof: O1W(0.333333)
8.a Secondary CH2 refined with riding coordinates:
 C3E(H3EA,H3EB), C2E(H2EA,H2EB), C6E(H6EA,H6EB), C8E(H8EA,H8EB)
8.b Aromatic/amide H refined with riding coordinates:
 C2'(H2'), C2(H2), C13'(H13'), C9'(H9'), C10'(H10'), C11'(H11'), C12'(H12'),
 C15'(H15'), C16'(H16'), C16(H16), C15(H15), C13(H13), C12(H12), C11(H11),
 C10(H10), C9(H9), C5(H5), C5'(H5'), C6'(H6'), C7(H7), C6(H6)
8.c Fitted hexagon refined as free rotating group:
 C13'(C8',C9',C10',C11',C12'), C15'(C16',C17,C16,C15,C14), C8(C13,C12,C11,C10,
 C9), C5(C4,C5',C6',C7,C6)
8.d Idealised Me refined as rotating group:
 C1E(H1EA,H1EB,H1EC), C4E(H4EA,H4EB,H4EC), C5E(H5EA,H5EB,H5EC), C7E(H7EA,H7EB,
 H7EC)
8.e Idealised tetrahedral OH refined as rotating group:
 O1E(H1E), O3E(H3E)
;
_shelx_res_checksum              20220
_shelx_hkl_checksum              81445
_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
;