Tetraphenylethylene-based blue light-emitting organic salt crystals
Hu, Huifen; Yan, Yukun; Yang, Chengling; Wang, Wei; CrystEngComm 27 (2025) 625–633; doi:10.1039/D4CE01094A

data_7249706
_publ_section_title
;
 Tetraphenylethylene-based blue light-emitting organic salt crystals
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              625
_journal_page_last               633
_journal_paper_doi               10.1039/D4CE01094A
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C34 H28 O12 S4, C54 H52 N4'
_chemical_formula_sum            'C88 H80 N4 O12 S4'
_chemical_formula_weight         1513.80
_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             2022-11-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-09-28 deposited with the CCDC.	2024-12-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.403(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2402(4)
_cell_length_b                   39.0334(13)
_cell_length_c                   19.5745(6)
_cell_measurement_reflns_used    7713
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.4590
_cell_measurement_theta_min      3.7520
_cell_volume                     9704.6(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.945
_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    -36.00  39.00   0.50    6.00    --    0.00  82.00-120.00  150
  2  \w    -29.00  36.00   0.50    6.00    --    0.00 -82.00 -60.00  130
  3  \w     26.00 129.00   0.50   10.00    --  101.90 -57.00  60.00  206
  4  \w     74.00 159.00   0.50   10.00    --  101.90  57.00-150.00  170
  5  \w     47.00 135.00   0.50   10.00    --  101.90 -19.00-180.00  176
  6  \w     12.00 136.00   0.50   10.00    --  101.90 -82.00  60.00  248
  7  \w     12.00  38.00   0.50   10.00    --  101.90 -19.00-180.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1110795000
_diffrn_orient_matrix_UB_12      -0.0142309000
_diffrn_orient_matrix_UB_13      -0.0348395000
_diffrn_orient_matrix_UB_21      -0.0400046000
_diffrn_orient_matrix_UB_22      0.0365536000
_diffrn_orient_matrix_UB_23      -0.0223169000
_diffrn_orient_matrix_UB_31      0.0276839000
_diffrn_orient_matrix_UB_32      -0.0045062000
_diffrn_orient_matrix_UB_33      -0.0708084000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0676
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -49
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            41086
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.400
_diffrn_reflns_theta_min         3.660
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    1.327
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71400
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.036
_exptl_crystal_description       plate
_exptl_crystal_F_000             3184
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.233
_refine_diff_density_min         -0.889
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     929
_refine_ls_number_reflns         19254
_refine_ls_number_restraints     2025
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.2470
_refine_ls_R_factor_gt           0.2048
_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^)+(0.0500P)^2^+79.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4046
_refine_ls_wR_factor_ref         0.4240
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11309
_reflns_number_total             19254
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce01094a2.cif
_cod_data_source_block           8_sq
_cod_depositor_comments
'Adding full bibliography for 7249703--7249706.cif.'
_cod_database_code               7249706
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 98.82
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C54-C53 = C15-C14
 1.55 with sigma of 0.02
 S1-O1 = S1-O2 = S1-O3 = S2-O4 = S2-O5 = S2-O6 = S3-O7 = S3-O8 = S3-O9 = S4-
 O10 = S4-O11 = S4-O12
 1.58 with sigma of 0.02
 N1-C14 = N3-C40 = N4-C53
 1.47 with sigma of 0.02
 C53-C54
 1.55 with sigma of 0.02
 C41-C40
 1.55 with sigma of 0.02
 C28-C27
 1.55 with sigma of 0.02
 N4-C54
 2.55 with sigma of 0.04
 C39-C40 \\sim C40-C38
 with sigma of 0.02
 C26-C27 \\sim C27-C25
 with sigma of 0.02
3. Restrained planarity
 N2, C22, C23, C24, C25, C26, C27
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C65 \\sim C66 \\sim C67 \\sim C68 \\sim C69 \\sim C70: within 1.7A with sigma
of 0.01 and sigma for terminal atoms of 0.02 within 1.7A
N2 \\sim C22 \\sim C23 \\sim C24 \\sim C25 \\sim C26: within 1.7A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 1.7A
C55 \\sim C56 \\sim C57 \\sim C58 \\sim C59 \\sim C60 \\sim C61 \\sim C62 \\sim
C63 \\sim C64 \\sim C65 \\sim C66 \\sim C67 \\sim C68 \\sim C69 \\sim C70 \\sim
C71 \\sim C72 \\sim C73 \\sim C74 \\sim C75 \\sim C76 \\sim C77 \\sim C78 \\sim
C79 \\sim C80 \\sim C81 \\sim C82 \\sim C83 \\sim C84 \\sim C85 \\sim C86 \\sim
C87 \\sim C88 \\sim C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7
\\sim C8 \\sim C9 \\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15
\\sim C16 \\sim C17 \\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C26
\\sim C25 \\sim C24 \\sim C23 \\sim C27 \\sim C28 \\sim C29 \\sim C30 \\sim C31
\\sim C32 \\sim C33 \\sim C34 \\sim C35 \\sim C36 \\sim C37 \\sim C38 \\sim C39
\\sim C40 \\sim C41 \\sim C42 \\sim C43 \\sim C44 \\sim C45 \\sim C46 \\sim C47
\\sim C48 \\sim C49 \\sim C50 \\sim C51 \\sim C52 \\sim C53 \\sim C54 \\sim N1
\\sim N4 \\sim N2 \\sim N3: within 3A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 3A
O1 \\sim O2 \\sim O3 \\sim O4 \\sim O5 \\sim O6 \\sim O7 \\sim O8 \\sim O9
\\sim O10 \\sim O11 \\sim O12 \\sim S1 \\sim S2 \\sim S3 \\sim S4: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
5.a Secondary CH2 refined with riding coordinates:
 C56(H56A,H56B), C58(H58A,H58B), C60(H60A,H60B), C61(H61A,H61B), C63(H63A,
 H63B), C64(H64A,H64B), C14(H14A,H14B), C27(H27A,H27B), C40(H40A,H40B),
 C53(H53A,H53B)
5.b Aromatic/amide H refined with riding coordinates:
 C66(H66), C67(H67), C69(H69), C70(H70), C72(H72), C73(H73), C75(H75),
 C76(H76), C78(H78), C79(H79), C81(H81), C82(H82), C84(H84), C85(H85), C87(H87),
  C88(H88), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12),
 C13(H13), C17(H17), C18(H18), C20(H20), C21(H21), C26(H26), C25(H25), C24(H24),
  C23(H23), C30(H30), C31(H31), C33(H33), C34(H34), C36(H36), C37(H37),
 C38(H38), C39(H39), C43(H43), C44(H44), C46(H46), C47(H47), C49(H49), C50(H50),
  C51(H51), C52(H52)
5.c Fitted hexagon refined as free rotating group:
 C65(C66,C67,C68,C69,C70), C83(C84,C85,C86,C87,C88), C22(C26,N2,C25,C24,C23),
 C35(C36,C37,C38,N3,C39)
5.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C28(H28A,H28B,H28C), C41(H41A,H41B,H41C), C54(H54A,H54B,
 H54C)
;
_shelx_res_checksum              95333
_shelx_fab_checksum              72493
_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 1.940
_oxdiff_exptl_absorpt_empirical_full_min 0.677