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_7134675
_publ_section_title
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 Donor/acceptor-substituted radiaannulene segments of 6,6,12-graphyne
;
_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         'C107.351 H109.132 O4 Si4, 3.694(C H Cl3)'
_chemical_formula_sum            'C111.05 H112.8 Cl11.07 O4 Si4'
_chemical_formula_weight         2016.20
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-05-04
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7205)
;
_audit_update_record
;
2025-05-05 deposited with the CCDC.	2025-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                72.067(2)
_cell_angle_beta                 86.454(2)
_cell_angle_gamma                81.331(2)
_cell_formula_units_Z            1
_cell_length_a                   10.9872(6)
_cell_length_b                   13.9513(7)
_cell_length_c                   18.9119(10)
_cell_measurement_reflns_used    9865
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      25.451
_cell_measurement_theta_min      2.264
_cell_volume                     2726.2(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 0.990
_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  0.1209
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            210113
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.689
_diffrn_reflns_theta_min         1.549
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.375
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.7037
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0938 before and 0.0536 after correction.
The Ratio of minimum to maximum transmission is 0.9434.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_description       needle
_exptl_crystal_F_000             1055
_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         0.881
_refine_diff_density_min         -1.154
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     710
_refine_ls_number_reflns         15315
_refine_ls_number_restraints     146
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1426
_refine_ls_R_factor_gt           0.0880
_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^)+(0.1265P)^2^+4.4535P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2324
_refine_ls_wR_factor_ref         0.2848
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9310
_reflns_number_total             15315
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02685g2.cif
_cod_data_source_block           mo_d8v6575_0m
_cod_depositor_comments
'Adding full bibliography for 7134672--7134675.cif.'
_cod_original_formula_sum        'C111.05 H112.80 Cl11.07 O4 Si4'
_cod_database_code               7134675
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.963
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H5 of C01Q, H3 of C3, H010 of C010, H017 of C017, H019
  of C019, H013 of C013, H015 of C015, H016 of C016, H01U of C01J, H2 of C01P,
  H01Z of C01M, H01M of C01F, H01Q of C01H, H4 of C4, H9 of C9, H00S of C00S,
  H00U of C00U, H00Y of C00Y, H00I of C00I, H00K of C00K
 At 1.5 times of:
  All C(H,H,H) groups, H1 of C1
2. Restrained distances
 C9-C6 = C9-C10 = C1-C01M = C01M-C01K = C01J-C2
 1.5 with sigma of 0.02
 Si02-C10 = C10A-Si02 = C6A-Si02
 2.85 with sigma of 0.02
 C6-Si02
 2.85 with sigma of 0.001
 Si02-C01J = Si02-C9 = Si02-C01M
 1.9 with sigma of 0.02
 C6-C9 \\sim C6A-C9
 with sigma of 0.02
 Si01-C01F \\sim Si01-C01H \\sim Si01-C013
 with sigma of 0.02
 C01J-C2 \\sim C01J-C2A
 with sigma of 0.02
 C9-C10 \\sim C9-C10A
 with sigma of 0.02
 Si02-C9 \\sim Si02-C9A
 with sigma of 0.02
 C6-C9 \\sim C6-C9A
 with sigma of 0.02
 C9-C10 \\sim C9A-C10
 with sigma of 0.02
 C9-C10A \\sim C9A-C10A
 with sigma of 0.02
 C9-C6A \\sim C9A-C6A
 with sigma of 0.02
 Cl03-C01P \\sim Cl-C01Q
 with sigma of 0.02
 C01P-Cl3 \\sim C01Q-Cl3A
 with sigma of 0.02
 C01P-Cl2 \\sim C01Q-Cl2A
 with sigma of 0.02
 C01L-C01F \\sim C01I-C01F \\sim C01H-C01G \\sim C01O-C01H \\sim C01B-C013
\\sim C01E-C013
 with sigma of 0.02
 Cl03-Cl3 \\sim Cl-Cl3A
 with sigma of 0.04
 Cl03-Cl2 \\sim Cl-Cl2A
 with sigma of 0.04
 Cl3-Cl2 \\sim Cl3A-Cl2A
 with sigma of 0.04
 C01K-C01M \\sim C7-C01M
 with sigma of 0.02
 C01M-C1 \\sim C01M-C1A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C01P \\sim Cl03 \\sim Cl3 \\sim Cl2 \\sim C01Q \\sim Cl \\sim Cl3A \\sim Cl2A:
within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C1 \\sim C01M \\sim C7 \\sim C01K \\sim C1A: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
Uanis(C1A) = Uanis(C01K)
Uanis(C6A) = Uanis(C10A)
Uanis(C6) = Uanis(C10)
Uanis(C01J) = Uanis(C9A)
4. Others
 Sof(Cl03)=Sof(C01P)=Sof(H2)=Sof(Cl3)=Sof(Cl2)=FVAR(1)
 Sof(C01Q)=Sof(H5)=Sof(Cl)=Sof(Cl3A)=Sof(Cl2A)=FVAR(2)
 Sof(C9)=Sof(H9)=Sof(C10A)=Sof(H10D)=Sof(H10E)=Sof(H10F)=Sof(C6A)=Sof(H6AA)=
 Sof(H6AB)=1-FVAR(3)
 Sof(C6)=Sof(H6A)=Sof(H6B)=Sof(H6C)=Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=
 Sof(C9A)=FVAR(3)
 Sof(H01U)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(H2AC)=Sof(C5)=Sof(H5A)=Sof(H5B)=
 Sof(H5C)=1-FVAR(4)
 Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=FVAR(4)
 Sof(C3)=Sof(H3)=Sof(Cl1)=Sof(Cl4)=Sof(Cl8)=1-FVAR(5)
 Sof(C4)=Sof(H4)=Sof(Cl5)=Sof(Cl6)=Sof(Cl7)=FVAR(5)
 Sof(C1A)=Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(H7C)=1-FVAR(6)
 Sof(C01K)=Sof(H01Z)=Sof(C1)=FVAR(6)
5.a Free rotating group:
 C4(Cl5,Cl6,Cl7), C3(Cl1,Cl4,Cl8)
5.b Ternary CH refined with riding coordinates:
 C013(H013), C01F(H01M), C01H(H01Q), C01J(H01U), C01M(H01Z), C01P(H2), C9(H9),
 C4(H4), C3(H3), C01Q(H5)
5.c Aromatic/amide H refined with riding coordinates:
 C00I(H00I), C00K(H00K), C00S(H00S), C00U(H00U), C00Y(H00Y), C010(H010),
 C015(H015), C016(H016), C017(H017), C019(H019)
5.d X=CH2 refined with riding coordinates:
 C6A(H6AA,H6AB)
5.e Idealised Me refined as rotating group:
 C01A(H01A,H01B,H01C), C01B(H01D,H01E,H01F), C01C(H01G,H01H,H01I), C01E(H01J,
 H01K,H01L), C01G(H01N,H01O,H01P), C01I(H01R,H01S,H01T), C01K(H01V,H01W,H01X),
 C01L(H01Y,H,HA), C01O(H01,HB,HC), C6(H6A,H6B,H6C), C10(H10A,H10B,H10C), C2(H2A,
 H2B,H2C), C10A(H10D,H10E,H10F), C2A(H2AA,H2AB,H2AC), C5(H5A,H5B,H5C), C7(H7A,
 H7B,H7C)
;
_shelx_res_checksum              4677
_shelx_hkl_checksum              66607
_olex2_submission_special_instructions 'No special instructions were received'