Benzo[de]isoquinoline-1,3-dione condensed asymmetric azaacenes as strong acceptors
Zhou, Pengxin; Deng, Lanlan; Han, Zengtao; Zhao, Xiaolong; Zhang, Zhe; Huo, Shuhui; RSC Advances 12 (2022) 13480–13486; doi:10.1039/D2RA01074G

data_7244891
_publ_section_title
;
 Benzo[de]isoquinoline-1,3-dione condensed asymmetric azaacenes as strong
 acceptors
;
_journal_issue                   21
_journal_name_full               'RSC Advances'
_journal_page_first              13480
_journal_page_last               13486
_journal_paper_doi               10.1039/D2RA01074G
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C48 H59 N5 O2 S Si2'
_chemical_formula_sum            'C48 H59 N5 O2 S Si2'
_chemical_formula_weight         826.24
_chemical_name_systematic        BQD-TZ
_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             2021-10-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-02-08 deposited with the CCDC.	2022-04-19 downloaded from the CCDC.
;
_cell_angle_alpha                102.994(2)
_cell_angle_beta                 99.015(2)
_cell_angle_gamma                100.350(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0570(2)
_cell_length_b                   17.2302(4)
_cell_length_c                   17.4330(3)
_cell_measurement_reflns_used    12970
_cell_measurement_temperature    149.99(11)
_cell_measurement_theta_max      77.1310
_cell_measurement_theta_min      2.6840
_cell_volume                     2270.21(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_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      149.99(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.942
_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    -90.00 -65.00   0.50    1.20    --  -47.57 137.00  55.00   50
  2  \w    -87.00 -61.00   0.50    1.20    --  -47.57 132.00-121.00   52
  3  \w     54.00 102.00   0.50    1.20    --   47.57-137.00  -8.00   96
  4  \w     72.00 119.00   0.50    1.20    --   47.57 137.00  55.00   94
  5  \w     50.00  92.00   0.50    1.20    --   47.57-132.00 168.00   84
  6  \w     74.00 120.00   0.50    1.20    --   47.57 132.00-121.00   92
  7  \w   -118.00 -72.00   0.50    2.30    -- -100.00 137.00  55.00   92
  8  \w   -169.00 -79.00   0.50    2.30    -- -100.00-132.00 168.00  180
  9  \w   -114.00 -89.00   0.50    2.30    -- -100.00 132.00-121.00   50
 10  \w   -124.00 -99.00   0.50    2.30    -- -100.00-137.00  -8.00   50
 11  \w     83.00 119.00   0.50    2.30    --  107.75-137.00  -8.00   72
 12  \w    123.00 148.00   0.50    2.30    --  107.75 132.00-121.00   50
 13  \w     35.00 116.00   0.50    2.30    --  107.75-132.00 168.00  162
 14  \w     76.00 126.00   0.50    2.30    --  107.75 137.00  55.00  100
 15  \w   -114.00 -35.00   0.50    1.20    --  -47.57 -57.00 120.00  158
 16  \w    -27.00  27.00   0.50    1.20    --  -47.57  19.00  60.00  108
 17  \w     -9.00  21.00   0.50    1.20    --   47.57 -19.00-120.00   60
 18  \w     26.00  96.00   0.50    1.20    --   47.57  77.00-120.00  140
 19  \w    -27.00  23.00   0.50    1.20    --   47.57 -19.00 -30.00  100
 20  \w    -75.00 -28.00   0.50    2.30    -- -100.00 125.00 150.00   94
 21  \w   -166.00 -92.00   0.50    2.30    -- -100.00 -99.00 -60.00  148
 22  \w   -106.00 -80.00   0.50    2.30    -- -100.00  77.00-120.00   52
 23  \w    -69.00 -29.00   0.50    2.30    -- -100.00  57.00 120.00   80
 24  \w   -173.00-127.00   0.50    2.30    -- -100.00 -37.00-180.00   92
 25  \w    -65.00 -39.00   0.50    2.30    -- -100.00  77.00-120.00   52
 26  \w   -101.00 -76.00   0.50    2.30    -- -100.00 125.00 150.00   50
 27  \w    -58.00 -28.00   0.50    2.30    -- -100.00  57.00 -90.00   60
 28  \w   -115.00 -88.00   0.50    2.30    -- -100.00 -37.00-180.00   54
 29  \w   -171.00-101.00   0.50    2.30    -- -100.00 -37.00   0.00  140
 30  \w   -175.00 -97.00   0.50    2.30    -- -100.00 -19.00  30.00  156
 31  \w     73.00  98.00   0.50    2.30    --  107.75 -99.00  60.00   50
 32  \w     37.00  69.00   0.50    2.30    --  107.75 -99.00  60.00   64
 33  \w    112.00 172.00   0.50    2.30    --  107.75  19.00-120.00  120
 34  \w     42.00  83.00   0.50    2.30    --  107.75 -77.00-150.00   82
 35  \w     37.00  62.00   0.50    2.30    --  107.75 -57.00 -60.00   50
 36  \w     71.00 104.00   0.50    2.30    --  107.75 -99.00 150.00   66
 37  \w     71.00 101.00   0.50    2.30    --  107.75 -99.00 -30.00   60
 38  \w     36.00  63.00   0.50    2.30    --  107.75 -99.00 -30.00   54
 39  \w     43.00  97.00   0.50    2.30    --  107.75 -99.00  30.00  108
 40  \w     40.00  92.00   0.50    2.30    --  107.75 -99.00   0.00  104
 41  \w     35.00  62.00   0.50    2.30    --  107.75 -57.00 120.00   54
 42  \w     35.00  61.00   0.50    2.30    --  107.75 -57.00-120.00   52
 43  \w     81.00 106.00   0.50    2.30    --  107.75 -99.00-180.00   50
 44  \w    100.00 152.00   0.50    2.30    --  107.75  37.00 120.00  104
 45  \w     40.00  66.00   0.50    2.30    --  107.75 -99.00-180.00   52
 46  \w     38.00  63.00   0.50    2.30    --  107.75 -57.00-150.00   50
 47  \w     36.00  61.00   0.50    2.30    --  107.75 -57.00 -30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0466059000
_diffrn_orient_matrix_UB_12      -0.0590024000
_diffrn_orient_matrix_UB_13      -0.0848086000
_diffrn_orient_matrix_UB_21      -0.0017374000
_diffrn_orient_matrix_UB_22      0.0729101000
_diffrn_orient_matrix_UB_23      -0.0373400000
_diffrn_orient_matrix_UB_31      0.1930616000
_diffrn_orient_matrix_UB_32      0.0080381000
_diffrn_orient_matrix_UB_33      -0.0012065000
_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  0.0567
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            29210
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.463
_diffrn_reflns_theta_min         2.658
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.474
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83161
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_description       needle
_exptl_crystal_F_000             884
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     565
_refine_ls_number_reflns         9098
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0526
_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^)+(0.0730P)^2^+0.7220P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1346
_refine_ls_wR_factor_ref         0.1412
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7582
_reflns_number_total             9098
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra01074g2.cif
_cod_data_source_block           denglanlan_1025-1_auto
_cod_database_code               7244891
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.66
_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
 Si2-C46 \\sim Si2-C49
 with sigma of 0.02
 C43-C46 \\sim C43-C49
 with sigma of 0.02
 C46-C48 \\sim C49-C48
 with sigma of 0.02
 C46-C48 \\sim C46-C50
 with sigma of 0.02
 C48-C49 \\sim C50-C49
 with sigma of 0.02
 C43-C46 \\sim C51-C46
 with sigma of 0.02
 C43-C49 \\sim C51-C49
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C51) \\sim Ueq, Uanis(C43) \\sim Ueq, Uanis(C46) \\sim Ueq, Uanis(C49)
\\sim Ueq, Uanis(C50) \\sim Ueq, Uanis(C48) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: C43(0.7) H43A(0.7) H43B(0.7) H43C(0.7) C46(0.65) H46(0.65)
 C48(0.35) H48A(0.35) H48B(0.35) H48C(0.35) C49(0.35) H49(0.35) C50(0.65)
 H50A(0.65) H50B(0.65) H50C(0.65) C51(0.3) H51A(0.3) H51B(0.3) H51C(0.3)
5.a Ternary CH refined with riding coordinates:
 C22(H22), C25(H25), C29(H29), C33(H33), C38(H38), C46(H46), C49(H49)
5.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C28(H28A,H28B), C32(H32A,H32B), C34(H34A,H34B), C35(H35A,H35B)
5.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C15(H15), C16(H16), C18(H18)
5.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C36(H36A,H36B,H36C), C37(H37A,H37B,
 H37C), C39(H39A,H39B,H39C), C40(H40A,H40B,H40C), C41(H41A,H41B,H41C), C42(H42A,
 H42B,H42C), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C), C45(H45A,H45B,H45C),
 C47(H47A,H47B,H47C), C48(H48A,H48B,H48C), C50(H50A,H50B,H50C), C51(H51A,H51B,
 H51C)
;
_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 2.911
_oxdiff_exptl_absorpt_empirical_full_min 0.438