Donor/acceptor-substituted radiaannulene segments of 6,6,12-graphyne
Krøll, Peter Lundgård; Strandfelt, Asger; Jokumsen, Maria Harbo; Nielsen, Mogens Brøndsted; Chemical Communications 61 (2025) 9416–9419; doi:10.1039/D5CC02685G

data_7134673
_publ_section_title
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 Donor/acceptor-substituted radiaannulene segments of 6,6,12-graphyne
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_journal_issue                   52
_journal_name_full               'Chemical Communications'
_journal_page_first              9416
_journal_page_last               9419
_journal_paper_doi               10.1039/D5CC02685G
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         '2(C108 H126 N4 Si4), 1.835(H)'
_chemical_formula_sum            'C216 H253.84 N8 Si8'
_chemical_formula_weight         3186.82
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-05-02
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7205)
;
_audit_update_record
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2025-05-05 deposited with the CCDC.	2025-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.927(9)
_cell_angle_gamma                90
_cell_formula_units_Z            1
_cell_length_a                   15.836(4)
_cell_length_b                   14.482(5)
_cell_length_c                   21.301(7)
_cell_measurement_reflns_used    1552
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      20.657
_cell_measurement_theta_min      2.374
_cell_volume                     4882(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Venture with Photon III 28'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2554
_diffrn_reflns_av_unetI/netI     0.1134
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            81138
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.713
_diffrn_reflns_theta_max         24.713
_diffrn_reflns_theta_min         1.577
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0958 before and 0.0662 after correction.
The Ratio of minimum to maximum transmission is 0.8964.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear dark brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.084
_exptl_crystal_description       needle
_exptl_crystal_F_000             1718
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CHCl3 and heptane'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.244
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.0019(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     547
_refine_ls_number_reflns         8320
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.1990
_refine_ls_R_factor_gt           0.0961
_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^)+(0.1275P)^2^+9.0492P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2336
_refine_ls_wR_factor_ref         0.3120
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3824
_reflns_number_total             8320
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02685g2.cif
_cod_data_source_block           mo_d8v6578_0m
_cod_depositor_comments
'Adding full bibliography for 7134672--7134675.cif.'
_cod_database_code               7134673
_shelx_shelxl_version_number     2019/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All Si(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Si1-C2 \\sim Si1-C2A
 with sigma of 0.02
 C2-C9A \\sim C2A-C9B
 with sigma of 0.02
 C2-C3A \\sim C2A-C3B
 with sigma of 0.02
 Si1-C9A \\sim Si1-C9B
 with sigma of 0.04
 Si1-C3A \\sim Si1-C3B
 with sigma of 0.04
 C9A-C3A \\sim C9B-C3B
 with sigma of 0.04
 Si1-C5 \\sim Si1-C5A
 with sigma of 0.02
 C5-C1 \\sim C5A-C1A
 with sigma of 0.02
 C5-C4 \\sim C5A-C4A
 with sigma of 0.02
 Si1-C1 \\sim Si1-C1A
 with sigma of 0.04
 Si1-C4 \\sim Si1-C4A
 with sigma of 0.04
 C1-C4 \\sim C1A-C4A
 with sigma of 0.04
 Si1-C7 \\sim Si1-C7A
 with sigma of 0.02
 C3-C7 \\sim C8-C7A
 with sigma of 0.02
 C6-C7 \\sim C6A-C7A
 with sigma of 0.02
 Si1-C3 \\sim Si1-C8
 with sigma of 0.04
 Si1-C6 \\sim Si1-C6A
 with sigma of 0.04
 C3-C6 \\sim C8-C6A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C2) = Uanis(C3A) = Uanis(C9A) = Uanis(C9B) = Uanis(C2A) = Uanis(C3B)
Uanis(C4) = Uanis(C4A) = Uanis(C5A) = Uanis(C5) = Uanis(C1) = Uanis(C1A)
Uanis(C6A) = Uanis(C7A) = Uanis(C3) = Uanis(C8) = Uanis(C7) = Uanis(C6)
Uanis(C01G) = Uanis(C019)
4. Others
 Sof(C3B)=Sof(H3BA)=Sof(H3BB)=Sof(H3BC)=Sof(C2A)=Sof(H2A)=Sof(C9B)=Sof(H9BA)=
 Sof(H9BB)=Sof(H9BC)=1-FVAR(1)
 Sof(C2)=Sof(H2)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(H9AC)=Sof(C3A)=Sof(H3AA)=
 Sof(H3AB)=Sof(H3AC)=FVAR(1)
 Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(H4AC)=Sof(C5A)=Sof(H5A)=Sof(C1A)=Sof(H1AA)=
 Sof(H1AB)=Sof(H1AC)=1-FVAR(2)
 Sof(C5)=Sof(H5)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C4)=Sof(H4A)=Sof(H4B)=
 Sof(H4C)=FVAR(2)
 Sof(HB)=Sof(C6A)=Sof(H6AA)=Sof(H6AB)=Sof(H6AC)=Sof(C7A)=Sof(H7A)=Sof(C8)=
 Sof(H8A)=Sof(H8B)=Sof(H8C)=1-FVAR(3)
 Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(H3C)=Sof(C6)=Sof(H6A)=Sof(H6B)=Sof(H6C)=Sof(C7)=
 Sof(H7)=FVAR(3)
 Fixed Sof: H019(0.5) H01P(0.5) C11(0.5) H11A(0.5) H11B(0.5) H11C(0.5)
 C25(0.5) H25A(0.5) H25B(0.5) H25C(0.5)
5.a Ternary CH refined with riding coordinates:
 C011(H011), C019(H019), C019(H01P), C5(H5), C2(H2), C2A(H2A), C5A(H5A),
 C7(H7), C7A(H7A)
5.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00C(H00C), C00E(H00E), C00F(H00F), C00J(H00J), C00N(H00N),
 C00O(H00O), C00R(H00R), C00U(H00U), C00W(H00W)
5.c Idealised Me refined as rotating group:
 C013(H01A,H01B,H01C), C014(H01D,H01E,H01F), C015(H01G,H01H,H01I), C016(H01J,
 H01K,H01L), C017(H01M,H01N,H01O), C01A(H01Q,H01R,H01S), C01B(H01T,H01U,H01V),
 C01D(H01W,H01X,H01Y), C01F(H01Z,H,HA), C11(H11A,H11B,H11C), C25(H25A,H25B,
 H25C), C1(H1A,H1B,H1C), C9A(H9AA,H9AB,H9AC), C3A(H3AA,H3AB,H3AC), C3B(H3BA,
 H3BB,H3BC), C9B(H9BA,H9BB,H9BC), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C4A(H4AA,
 H4AB,H4AC), C1A(H1AA,H1AB,H1AC), C6(H6A,H6B,H6C), C6A(H6AA,H6AB,H6AC), C8(H8A,
 H8B,H8C)
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_shelx_res_checksum              9276
_shelx_hkl_checksum              96440
_olex2_submission_special_instructions 'No special instructions were received'