Stereoselective synthesis of heterocyclic tetraphenylethylene analogues with configuration-dependent solid-state luminescence
Seinfeld, Mathilde; Rouillon, Jean; Rullan, Raphael; Jeanneau, Erwann; Steinmann, Stephan N.; Andraud, Chantal; Le Bahers, Tangui; Monnereau, Cyrille; Chemical Science 16 (2025) 10523–10531; doi:10.1039/D4SC08333D

data_1574574
_publ_section_title
;
 Stereoselective synthesis of heterocyclic tetraphenylethylene analogues
 with configuration-dependent solid-state luminescence
;
_journal_issue                   23
_journal_name_full               'Chemical Science'
_journal_page_first              10523
_journal_page_last               10531
_journal_paper_doi               10.1039/D4SC08333D
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C32 H26 N6'
_chemical_formula_sum            'C32 H26 N6'
_chemical_formula_weight         494.59
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2024-11-28 deposited with the CCDC.	2025-05-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0736(12)
_cell_length_b                   14.8909(18)
_cell_length_c                   19.280(2)
_cell_measurement_reflns_used    4928
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      29.0440
_cell_measurement_theta_min      3.4270
_cell_volume                     2605.0(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4685
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.902
_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    -97.00 -35.00   1.00   10.00    --  -10.24 178.00-150.00   62
  2  \w    -97.00 -35.00   1.00   10.00    --  -10.24 178.00 -30.00   62
  3  \w    -43.00  36.00   1.00   10.00    --  -10.24  77.00-180.00   79
  4  \w      4.00  51.00   1.00   10.00    --   11.34 -99.00-180.00   47
  5  \w     10.00  28.00   1.00   10.00    --   11.34  77.00  90.00   18
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0073298000
_diffrn_orient_matrix_UB_12      -0.0395981000
_diffrn_orient_matrix_UB_13      0.0202139000
_diffrn_orient_matrix_UB_21      -0.0730342000
_diffrn_orient_matrix_UB_22      0.0054078000
_diffrn_orient_matrix_UB_23      0.0120616000
_diffrn_orient_matrix_UB_31      -0.0264967000
_diffrn_orient_matrix_UB_32      -0.0259182000
_diffrn_orient_matrix_UB_33      -0.0283557000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.902
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            17447
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.632
_diffrn_reflns_theta_min         2.833
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.547
_exptl_crystal_size_mid          0.501
_exptl_crystal_size_min          0.242
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.012(2)
_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   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3323
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.1019
_refine_ls_R_factor_gt           0.0669
_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^)+(0.0833P)^2^+1.7462P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1605
_refine_ls_wR_factor_ref         0.2028
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2326
_reflns_number_total             3323
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc08333d1.cif
_cod_data_source_block           (E)-DTS-1
_cod_depositor_comments
'Adding full bibliography for 1574574--1574575.cif.'
_cod_database_code               1574574
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C32 H26 N6'
_reflns_odcompleteness_completeness 99.64
_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
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16)
;
_olex2_date_sample_data_collection 2020-09-22
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a nylon loop in perfluoroether oil'
_olex2_submission_original_sample_id 'DTS BZ'
_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 1.318
_oxdiff_exptl_absorpt_empirical_full_min 0.802