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

data_1571774
_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(C H4 O)'
_chemical_formula_sum            'C33 H37 N O5'
_chemical_formula_weight         527.63
_chemical_name_common
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ET(1)*4CH3OH
;
_chemical_name_systematic
;
4-(2,4,6-triphenylpyridinium-1-yl)-phenolate tetramethanol solvate
;
_chemical_properties_physical    Moisture-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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                 95.70(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.425(3)
_cell_length_b                   19.26(7)
_cell_length_c                   13.112(4)
_cell_measurement_reflns_used    1800
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.9630
_cell_measurement_theta_min      2.3600
_cell_volume                     2620(10)
_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_pressure         1170000
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.374
_diffrn_measured_fraction_theta_max 0.190
_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  0.1627
_diffrn_reflns_av_unetI/netI     0.2355
_diffrn_reflns_Laue_measured_fraction_full 0.374
_diffrn_reflns_Laue_measured_fraction_max 0.190
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3529
_diffrn_reflns_point_group_measured_fraction_full 0.374
_diffrn_reflns_point_group_measured_fraction_max 0.190
_diffrn_reflns_theta_full        15.000
_diffrn_reflns_theta_max         26.801
_diffrn_reflns_theta_min         2.230
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.992
_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 orangish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_preparation       'crystallized in DAC,solvatochromic'
_exptl_crystal_recrystallization_method 'crystallized at high pressure'
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.119
_refine_diff_density_rms         0.033
_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   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         1064
_refine_ls_number_restraints     864
_refine_ls_restrained_S_all      0.762
_refine_ls_R_factor_all          0.2272
_refine_ls_R_factor_gt           0.0795
_refine_ls_shift/su_max          0.0
_refine_ls_shift/su_mean         0.0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1342P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1889
_refine_ls_wR_factor_ref         0.2803
_reflns_Friedel_coverage         0.000
_reflns_number_gt                380
_reflns_number_total             1064
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lt5066.cif
_cod_data_source_block           et1_meoh_1_17gpa
_cod_original_cell_volume        2620(9)
_cod_database_code               1571774
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.971
_exptl_absorpt_special_details
;
Data were collected at room temperature (295(2) K) and pressure of 1.17(2) GPa
(1170000 kPa).
;
_exptl_oxdiff_absorpt_process_details
;
Gaussian integration over a grid
of 16 x 16 x 16 points =  4096 total grid points
  Based upon method of Burnham (1966)

 Data corrected for diamond-anvil cell absorption
 Note that exptl_absorpt_correction_tmin and _tmax
 the total correction factors applied to the intensities
 The individual factors are: 
         range of dac transmission factors (min-max)      0.396     0.455
         range of gasket transmission (min-max)           0.917     1.000
         range of P media transmission (min-max)          1.000     1.000

 thickness of diamond anvil 1: 19.500 mm, mu =  0.0202 mm-1
       thickness of platten 1:  0.000 mm, mu =  0.0000 mm-1

 thickness of diamond anvil 2: 19.500 mm, mu =  0.0202 mm-1
       thickness of platten 2:  0.000 mm, mu =  0.0000 mm-1

    Gasket shadowing corrections were made based upon
    Gasket thickness = 300.0 microns, radius = 300.0 microns
    Gasket absorption coeff =        21.00 mm-1
    REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF 
 FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00

    Non-absorbing pressure medium
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 H1M_$1-O1
 2 with sigma of 0.02
 O1M-C1M \\sim O2M-C2M \\sim O3M-C3M \\sim O4M-C4M
 with sigma of 0.02
 C9'-C8' \\sim C8'-C13' \\sim C13'-C12' \\sim C12'-C11' \\sim C11'-C10' \\sim
C9'-C10' \\sim C8-C13 ~
 C13-C12 \\sim C12-C11 \\sim C11-C10 \\sim C9-C10 \\sim C9-C8 \\sim C5-C4 \\sim
C6-C5 \\sim C7-C6 \\sim C7-C6'
 \\sim C6'-C5' \\sim C5'-C4 \\sim C15-C14 \\sim C15'-C14 \\sim C16'-C15' \\sim
C17-C16' \\sim C17-C16 \\sim C16-
 C15
 with sigma of 0.02
 C2'-C1' \\sim C3-C2' \\sim C3-C2 \\sim C2-C1
 with sigma of 0.02
 C4-C3 \\sim C8-C1 \\sim C8'-C1'
 with sigma of 0.02
 N1-C1 \\sim N1-C1'
 with sigma of 0.02
 C14-C1 \\sim C14-C1'
 with sigma of 0.02
 N1-C15' \\sim N1-C15
 with sigma of 0.02
 C5-C3 \\sim C5'-C3
 with sigma of 0.02
 C4-C2 \\sim C4-C2'
 with sigma of 0.02
3. Restrained planarity
 C2, C1, N1, C1', C2', C3
 with sigma of 0.1
 C8', C13', C12', C11', C10', C9'
 with sigma of 0.1
 C9, C13, C12, C10, C8, C11
 with sigma of 0.1
 C5, C5', C6', C6, C4, C7
 with sigma of 0.1
 C15, C17, C16', C14, C16, C15'
 with sigma of 0.1
4. Rigid bond restraints
 O1M, C1M
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C15'
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O4M, C4M
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O3M, C3M
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C2M, O2M
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
Uanis(C11) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C1)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C3) \\sim Ueq, Uanis(C15') \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(O1) \\sim Ueq, Uanis(C4M) \\sim Ueq, Uanis(O4M) \\sim Ueq, Uanis(O2M)
\\sim Ueq, Uanis(C2M) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms
of 0.2
Uanis(O1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O2M) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
6. Rigid body (RIGU) restrains
 O1, C16, C1, C4, C9, C1M, C3M, C2M, C14, C12, C9', C11, C17, N1, C11'
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C13', O1, C17, C16, C16', C15, C15', C14, N1, C1, C1', C2, C8, C2', C8', C3,
 C13, C9, C9', C4, C12, C10, C10', C12', C5', C5, C11, C11', C6', C6, C7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
7. Others
 Fixed Uiso: H1M(0.2)
8.a Aromatic/amide H refined with riding coordinates:
 C10'(H10'), C9'(H9'), C5'(H5'), C6'(H6'), C13'(H13'), C16(H16), C16'(H16'),
 C15'(H15'), C11'(H11'), C6(H6), C5(H5), C15(H15), C13(H13), C9(H9), C7(H7),
 C2(H2), C2'(H2'), C11(H11), C12(H12), C10(H10), C12'(H12')
8.b Idealised Me refined as rotating group:
 C2M(H2MA,H2MB,H2MC), C1M(H1MA,H1MB,H1MC), C3M(H3MA,H3MB,H3MC), C4M(H4MA,H4MB,
 H4MC)
8.c Idealised tetrahedral OH refined as rotating group:
 O1M(H1M), O4M(H4M), O3M(H3M), O2M(H2M)
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_shelx_res_checksum              91113
_shelx_hkl_checksum              83148
_olex2_submission_special_instructions 'No special instructions were received'