Multiple effects of aromatic substituents on excited-state properties and singlet fission process in azaquinodimethane systems.
Zhao, Zhenxiang; Wang, Senhao; Shi, Xiaomei; Fu, Hongbing; Wang, Long; Chemical science 16 (2025) 5565–5572; doi:10.1039/d4sc06494a

data_1573937
_publ_section_title
;
 Multiple effects of aromatic substituents on excited-state properties and
 singlet fission process in azaquinodimethane systems.
;
_journal_issue                   13
_journal_name_full               'Chemical science'
_journal_page_first              5565
_journal_page_last               5572
_journal_paper_doi               10.1039/d4sc06494a
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C38 H38 N2 O2'
_chemical_formula_sum            'C38 H38 N2 O2'
_chemical_formula_weight         554.70
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2024-08-28
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-08-31 deposited with the CCDC.	2025-02-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.725(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.5360(12)
_cell_length_b                   5.5532(5)
_cell_length_c                   21.084(2)
_cell_measurement_reflns_used    1885
_cell_measurement_temperature    302.11(10)
_cell_measurement_theta_max      28.2330
_cell_measurement_theta_min      1.7440
_cell_volume                     1583.1(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_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)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      302.11(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.978
_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      2.00  72.00   1.00   15.00    --    3.89  21.00 150.00   70
  2  \w    -11.00   9.00   1.00   15.00    --    3.89 -21.00 -15.00   20
  3  \w     -7.00  23.00   1.00   15.00    --    3.89 -99.00   0.00   30
  4  \w      1.00  71.00   1.00   15.00    --    3.89  37.00-120.00   70
  5  \w     34.00  64.00   1.00   15.00    --   -6.24  37.00-180.00   30
  6  \w    -13.00  12.00   1.00   15.00    --   -6.24  37.00-180.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0058554000
_diffrn_orient_matrix_UB_12      -0.0119865000
_diffrn_orient_matrix_UB_13      0.0331389000
_diffrn_orient_matrix_UB_21      0.0509377000
_diffrn_orient_matrix_UB_22      -0.0282887000
_diffrn_orient_matrix_UB_23      0.0045703000
_diffrn_orient_matrix_UB_31      0.0110513000
_diffrn_orient_matrix_UB_32      0.1240050000
_diffrn_orient_matrix_UB_33      0.0042452000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_unetI/netI     0.0761
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            11716
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.720
_diffrn_reflns_theta_min         1.751
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_description       needle
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3270
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1386
_refine_ls_R_factor_gt           0.0750
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1420P)^2^+0.0768P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2220
_refine_ls_wR_factor_ref         0.2706
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1591
_reflns_number_total             3270
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc06494a2.cif
_cod_data_source_block           taiyun_1209_3_auto
_cod_depositor_comments
'Adding full bibliography for 1573937--1573938.cif.'
_cod_original_cell_volume        1583.1(2)
_cod_database_code               1573937
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.975
_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
 C15-C10
 1.4 with sigma of 0.01
3. Others
 Fixed Sof: C15(0.5) H15(0.5) C14(0.5) H14(0.5) H13(0.5) H13A(0.5) C12(0.5)
 H12(0.5) C11(0.5) H11(0.5) C11'(0.5) H11'(0.5) C12'(0.5) H12'(0.5) C14'(0.5)
 H14'(0.5) C15'(0.5) H15'(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C15(H15), C14(H14), C13(H13),
 C13(H13A), C12(H12), C11(H11), C11'(H11'), C12'(H12'), C14'(H14'), C15'(H15')
4.c Fitted hexagon refined as free rotating group:
 C10(C15,C14,C13,C12,C11)
4.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_shelx_res_checksum              27026
_shelx_hkl_checksum              70316
_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 3.406
_oxdiff_exptl_absorpt_empirical_full_min 0.448