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_7244890
_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         'C60 H63 N5 O2 Si2'
_chemical_formula_sum            'C60 H63 N5 O2 Si2'
_chemical_formula_weight         942.33
_chemical_name_systematic        BQD-AP
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-I 2y'
_space_group_name_H-M_alt        'I 1 2/m 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-02-07 deposited with the CCDC.	2022-04-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.138(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.5906(7)
_cell_length_b                   23.3490(7)
_cell_length_c                   16.1770(9)
_cell_measurement_reflns_used    10296
_cell_measurement_temperature    149.97(11)
_cell_measurement_theta_max      75.4980
_cell_measurement_theta_min      3.2890
_cell_volume                     5373.9(5)
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.97(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.869
_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   -110.00 -84.00   0.50    1.20    --  -45.45 -55.00  88.00   52
  2  \w    -41.00 -16.00   0.50    1.20    --  -45.45  55.00-128.00   50
  3  \w     31.00 117.00   0.50    1.20    --   45.45  55.00-128.00  172
  4  \w    -26.00  60.00   0.50    1.20    --   45.45 -55.00  88.00  172
  5  \w   -172.00 -91.00   0.50    4.00    -- -100.00 -55.00  88.00  162
  6  \w    -66.00 -29.00   0.50    4.00    -- -100.00  55.00-128.00   74
  7  \w    145.00 174.00   0.50    4.00    --  107.75  55.00-128.00   58
  8  \w   -116.00 -48.00   0.50    1.20    --  -45.45-179.00-120.00  136
  9  \w     -9.00  23.00   0.50    1.20    --   45.45 -19.00 -60.00   64
 10  \w   -172.00 -92.00   0.50    4.00    -- -100.00 -99.00-150.00  160
 11  \w    -73.00 -29.00   0.50    4.00    -- -100.00 125.00  90.00   88
 12  \w   -122.00 -84.00   0.50    4.00    -- -100.00 -77.00-180.00   76
 13  \w   -164.00-124.00   0.50    4.00    -- -100.00 -77.00-180.00   80
 14  \w    -69.00 -44.00   0.50    4.00    -- -100.00  57.00  60.00   50
 15  \w   -166.00 -83.00   0.50    4.00    -- -100.00-125.00-180.00  166
 16  \w    -68.00 -30.00   0.50    4.00    -- -100.00  57.00  90.00   76
 17  \w    -68.00 -43.00   0.50    4.00    -- -100.00  57.00 150.00   50
 18  \w    -64.00 -39.00   0.50    4.00    -- -100.00  57.00  30.00   50
 19  \w     36.00  61.00   0.50    4.00    --  107.75 -57.00  30.00   50
 20  \w    127.00 174.00   0.50    4.00    --  107.75  37.00 -30.00   94
 21  \w     37.00  62.00   0.50    4.00    --  107.75 -57.00 120.00   50
 22  \w     39.00 103.00   0.50    4.00    --  107.75 -77.00-180.00  128
 23  \w     85.00 139.00   0.50    4.00    --  107.75  77.00 -30.00  108
 24  \w     39.00 102.00   0.50    4.00    --  107.75 -99.00 -90.00  126
 25  \w    103.00 130.00   0.50    4.00    --  107.75  55.00-128.00   54
 26  \w    -92.00 -36.00   0.50    1.20    --  -47.57 -57.00   0.00  112
 27  \w     17.00  84.00   0.50    1.20    --   47.57-125.00 120.00  134
 28  \w    -23.00  38.00   0.50    1.20    --   47.57 -37.00-150.00  122
 29  \w     92.00 120.00   0.50    1.20    --   47.57  57.00  30.00   56
 30  \w     33.00  80.00   0.50    1.20    --   47.57  57.00  30.00   94
 31  \w   -172.00-139.00   0.50    4.00    -- -100.00 -37.00 -90.00   66
 32  \w   -123.00 -97.00   0.50    4.00    -- -100.00 -37.00 120.00   52
 33  \w   -115.00 -88.00   0.50    4.00    -- -100.00 -46.00 -19.49   54
 34  \w   -171.00-137.00   0.50    4.00    -- -100.00 -77.00  30.00   68
 35  \w   -106.00 -77.00   0.50    4.00    -- -100.00 -77.00 -30.00   58
 36  \w    -69.00 -44.00   0.50    4.00    -- -100.00  57.00   0.00   50
 37  \w   -130.00 -92.00   0.50    4.00    -- -100.00 -99.00  60.00   76
 38  \w   -119.00 -93.00   0.50    4.00    -- -100.00 -37.00   0.00   52
 39  \w   -129.00 -91.00   0.50    4.00    -- -100.00 -57.00  30.00   76
 40  \w   -165.00-126.00   0.50    4.00    -- -100.00 -77.00   0.00   78
 41  \w    -69.00 -35.00   0.50    4.00    -- -100.00  57.00 -90.00   68
 42  \w   -105.00 -80.00   0.50    4.00    -- -100.00 -77.00  30.00   50
 43  \w    -69.00 -44.00   0.50    4.00    -- -100.00  57.00  30.00   50
 44  \w   -116.00 -85.00   0.50    4.00    -- -100.00 -63.00 -24.98   62
 45  \w   -103.00 -77.00   0.50    4.00    -- -100.00 -77.00   0.00   52
 46  \w   -171.00-125.00   0.50    4.00    -- -100.00 -77.00 -30.00   92
 47  \w   -169.00-135.00   0.50    4.00    -- -100.00 -37.00 120.00   68
 48  \w   -114.00 -88.00   0.50    4.00    -- -100.00 -37.00 -30.00   52
 49  \w   -165.00-152.50   0.50    4.00    -- -100.00 -99.00  60.00   25
;
_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      -0.0105109000
_diffrn_orient_matrix_UB_12      0.0413179000
_diffrn_orient_matrix_UB_13      0.0694462000
_diffrn_orient_matrix_UB_21      0.1004790000
_diffrn_orient_matrix_UB_22      -0.0148342000
_diffrn_orient_matrix_UB_23      0.0679794000
_diffrn_orient_matrix_UB_31      0.0389708000
_diffrn_orient_matrix_UB_32      0.0492347000
_diffrn_orient_matrix_UB_33      -0.0380520000
_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  0.0706
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25004
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         88.186
_diffrn_reflns_theta_min         3.318
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.956
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34306
_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 orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_description       needle
_exptl_crystal_F_000             2008
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.688
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.00007(6)
_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   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5460
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1084
_refine_ls_R_factor_gt           0.0861
_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^)+(0.1357P)^2^+9.3883P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2363
_refine_ls_wR_factor_ref         0.2589
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4018
_reflns_number_total             5460
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra01074g2.cif
_cod_data_source_block           dengll_0919_auto
_cod_database_code               7244890
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.963
_reflns_odcompleteness_completeness 98.81
_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
 C23-C24
 1.55 with sigma of 0.01
3. Others
 Fixed Sof: H19A(0.5) H19B(0.5) H20A(0.5) H20B(0.5) H21A(0.5) H21B(0.5)
 C24(0.5) H24A(0.5) H24B(0.5) H24C(0.5)
4.a Ternary CH refined with riding coordinates:
 C27(H27), C30(H30), C33(H33)
4.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C16(H16), C17(H17)
4.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C31(H31A,H31B,
 H31C), C32(H32A,H32B,H32C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 3.622
_oxdiff_exptl_absorpt_empirical_full_min 0.366