Color-tunable emissive heptagon-embedded polycyclic aromatic dicarboximides
Kantarod, Kritchasorn; Soorukram, Darunee; Kuhakarn, Chutima; Surawatanawong, Panida; Wattanathana, Worawat; Reutrakul, Vichai; Leowanawat, Pawaret; Chemical Communications  (2022) –; doi:10.1039/D2CC03461A

data_7130348
_publ_section_title
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 Color-tunable emissive heptagon-embedded polycyclic aromatic
 dicarboximides
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_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC03461A
_journal_year                    2022
_chemical_formula_moiety         'C52 H35 N3 O2'
_chemical_formula_sum            'C52 H35 N3 O2'
_chemical_formula_weight         733.83
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-06-13 deposited with the CCDC.	2022-07-20 downloaded from the CCDC.
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_cell_angle_alpha                101.390(4)
_cell_angle_beta                 104.212(4)
_cell_angle_gamma                96.122(5)
_cell_formula_units_Z            2
_cell_length_a                   9.0827(12)
_cell_length_b                   14.2076(18)
_cell_length_c                   15.2875(19)
_cell_measurement_reflns_used    9750
_cell_measurement_temperature    298
_cell_measurement_theta_max      72.18
_cell_measurement_theta_min      4.93
_cell_volume                     1849.6(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'PHOTON 100 CMOS DETECTOR'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            'PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device       '\k-Geometry Diffractometer'
_diffrn_measurement_device_type  'BRUKER D8 VENTURE'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0125
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            63100
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.272
_diffrn_reflns_theta_min         3.216
_diffrn_source                   'X-ray tube'
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_target            Cu
_diffrn_source_type              'Micro focus tube'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.7089
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0734 before and 0.0396 after correction.
The Ratio of minimum to maximum transmission is 0.9407.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH2Cl2 and CH3OH'
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     515
_refine_ls_number_reflns         7167
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0426
_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^)+(0.0703P)^2^+0.4442P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1274
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6412
_reflns_number_total             7167
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc03461a2.cif
_cod_data_source_block           nap2car_rt_0m_a
_cod_database_code               7130348
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.969
_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.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C3(H3A,H3B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C25(H25), C24(H24), C28(H28), C11(H11), C15(H15), C10(H10), C27(H27),
 C21(H21), C22(H22), C51(H51), C16(H16), C42(H42), C33(H33), C30(H30), C45(H45),
  C39(H39), C43(H43), C31(H31), C32(H32), C36(H36), C44(H44), C38(H38),
 C37(H37), C48(H48), C50(H50), C49(H49)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              74867
_shelx_hkl_checksum              87350
_olex2_submission_special_instructions 'No special instructions were received'