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_7134674
_publ_section_title
;
 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
'C104 H113 O4.258 Si4, C0.587 H0.587 Cl0.885, C0.915 H0.915 Cl1.809'
_chemical_formula_sum            'C105.49 H114.49 Cl2.7 O4.26 Si4'
_chemical_formula_weight         1658.57
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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             2025-05-05
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_audit_update_record
;
2025-05-05 deposited with the CCDC.	2025-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                71.243(2)
_cell_angle_beta                 73.484(3)
_cell_angle_gamma                75.284(2)
_cell_formula_units_Z            1
_cell_length_a                   12.6006(8)
_cell_length_b                   14.1684(9)
_cell_length_c                   15.1207(10)
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      29.436
_cell_measurement_theta_min      2.503
_cell_volume                     2411.0(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 0.999
_diffrn_measured_fraction_theta_max 0.996
_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  0.0870
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            173884
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.539
_diffrn_reflns_theta_min         1.458
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7150
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1231 before and 0.0710 after correction.
The Ratio of minimum to maximum transmission is 0.9583.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'dull yellowish brown'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_description       plate
_exptl_crystal_F_000             883
_exptl_crystal_preparation       'Slow evaporation'
_exptl_crystal_recrystallization_method 'Slow evaporation'
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.120
_refine_diff_density_min         -1.225
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 8533 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.58(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1117
_refine_ls_number_reflns         29249
_refine_ls_number_restraints     2189
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0521
_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^)+(0.0501P)^2^+1.8723P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1483
_reflns_Friedel_coverage         0.988
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                20369
_reflns_number_total             29249
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02685g2.cif
_cod_data_source_block           mo_d8v6582_0m
_cod_depositor_comments
'Adding full bibliography for 7134672--7134675.cif.'
_cod_original_formula_sum        'C105.49 H114.49 Cl2.70 O4.26 Si4'
_cod_database_code               7134674
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.985
_diffrn_oxdiff_ac3_digest_hkl    01fc33494391b91ce8e19a17b8ce47e84f08fa
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H) groups, All C(H,H,H) groups
2. Restrained distances
 C018-C02B = C02B-C02V = C02V-C038 = C038-C03A = C03A-C02Y = C02Y-C018
 1.39 with sigma of 0.01
 C016-C01K = C01K-C02A = C02A-C02H = C02H-C02G = C02G-C036 = C036-C016
 1.39 with sigma of 0.01
 C5-C16 = C16-C2 = C2-C11 = C11-C9 = C9-C3 = C3-C5
 1.39 with sigma of 0.01
 C018-C02V \\sim C02B-C038 \\sim C02V-C03A \\sim C038-C02Y \\sim C03A-C018
\\sim C02Y-C02B
 with sigma of 0.02
 C016-C02A \\sim C01K-C02H \\sim C02A-C02G \\sim C02H-C036 \\sim C02G-C016
\\sim C036-C01K
 with sigma of 0.02
 C5-C2 \\sim C16-C11 \\sim C2-C9 \\sim C11-C3 \\sim C9-C5 \\sim C3-C16
 with sigma of 0.02
 C01Q-C5 \\sim C01Q-C1A
 with sigma of 0.02
 C5-C16 \\sim C1A-C16A
 with sigma of 0.02
 C5-C3 \\sim C1A-C3A
 with sigma of 0.02
 C16-C2 \\sim C16A-C2A
 with sigma of 0.02
 C9-C11 \\sim C9A-C11A
 with sigma of 0.02
 C9-C3 \\sim C9A-C3A
 with sigma of 0.02
 C11-C2 \\sim C11A-C2A
 with sigma of 0.02
 C01Q-C16 \\sim C01Q-C16A
 with sigma of 0.04
 C01Q-C3 \\sim C01Q-C3A
 with sigma of 0.04
 C5-C9 \\sim C1A-C9A
 with sigma of 0.04
 C5-C2 \\sim C1A-C2A
 with sigma of 0.04
 C16-C11 \\sim C16A-C11A
 with sigma of 0.04
 C16-C3 \\sim C16A-C3A
 with sigma of 0.04
 C9-C2 \\sim C9A-C2A
 with sigma of 0.04
 C11-C3 \\sim C11A-C3A
 with sigma of 0.04
 C018-C02B \\sim C10-C8
 with sigma of 0.02
 C018-C02Y \\sim C10-C12
 with sigma of 0.02
 C01S-C02Y \\sim C01S-C12
 with sigma of 0.02
 C02B-C02V \\sim C8-C7
 with sigma of 0.02
 C02V-C038 \\sim C7-C0
 with sigma of 0.02
 C02Y-C03A \\sim C12-C03B
 with sigma of 0.02
 C038-C03A \\sim C0-C03B
 with sigma of 0.02
 C018-C01S \\sim C10-C01S
 with sigma of 0.04
 C018-C02V \\sim C10-C7
 with sigma of 0.04
 C018-C03A \\sim C10-C03B
 with sigma of 0.04
 C01S-C03A \\sim C01S-C03B
 with sigma of 0.04
 C02B-C02Y \\sim C8-C12
 with sigma of 0.04
 C02B-C038 \\sim C8-C0
 with sigma of 0.04
 C02V-C03A \\sim C7-C03B
 with sigma of 0.04
 C02Y-C038 \\sim C12-C0
 with sigma of 0.04
 Cl3-Cl4 \\sim Cl3A-Cl4A
 with sigma of 0.04
3. Restrained planarity
 C018, C02B, C02V, C038, C03A, C02Y
 with sigma of 0.1
 C016, C01K, C02A, C02H, C02G, C036
 with sigma of 0.1
 C5, C16, C2, C11, C9, C3
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
Uanis(C1A) = Uanis(C5) = Uanis(C3) = Uanis(C3A) = Uanis(C9A) = Uanis(C9) =
Uanis(C11) = Uanis(C11A) = Uanis(C2) = Uanis(C2A) = Uanis(C16) = Uanis(C16A)
Uanis(C5) = Uanis(C1A) = Uanis(C3) = Uanis(C3A) = Uanis(C16) = Uanis(C16A) =
Uanis(C2A) = Uanis(C11A) = Uanis(C2) = Uanis(C9A) = Uanis(C11) = Uanis(C9)
Uanis(C00H) = Uanis(C021) = Uanis(C00I) = Uanis(C027)
Uanis(C00R) = Uanis(C01N)
Uanis(C017) = Uanis(C01U)
Uanis(C015) = Uanis(C016)
Uanis(C00Z) = Uanis(C01L)
Uanis(C00W) = Uanis(C01B)
Uanis(C029) = Uanis(C01J) = Uanis(C00K) = Uanis(C00J)
Uanis(C01P) = Uanis(C01M)
Uanis(C02D) = Uanis(C00F)
Uanis(C00P) = Uanis(C01D)
Uanis(Cl4A) = Uanis(Cl3)
Uanis(C00E) = Uanis(C02N)
Uanis(C00R) = Uanis(C01I)
Uanis(C00M) = Uanis(C02H)
Uanis(C01S) = Uanis(C01Q)
Uanis(Cl3) = Uanis(Cl4A)
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(C1A)=Sof(C16A)=Sof(H16A)=Sof(C3A)=Sof(H3AA)=Sof(C9A)=Sof(H9AA)=Sof(C11A)=
 Sof(C2A)=Sof(H2AA)=1-FVAR(1)
 Sof(C5)=Sof(C16)=Sof(H16)=Sof(C9)=Sof(H9A)=Sof(C11)=Sof(C2)=Sof(H2A)=Sof(C3)=
 Sof(H3A)=FVAR(1)
 Sof(C12)=Sof(C03B)=Sof(H03E)=Sof(C0)=Sof(H0)=Sof(C7)=Sof(C8)=Sof(H8A)=
 Sof(C10)=Sof(H10A)=1-FVAR(2)
 Sof(C018)=Sof(H018)=Sof(C02B)=Sof(H02N)=Sof(O02J)=Sof(C02V)=Sof(C02Y)=
 Sof(C038)=Sof(H038)=Sof(C03A)=Sof(H03D)=FVAR(2)
 Sof(C4)=Sof(H4A)=FVAR(3)
 Sof(C13)=Sof(H13)=FVAR(4)
7.a Ternary CH refined with riding coordinates:
 C00N(H00N), C00U(H00U), C00X(H00X), C01C(H01M), C01H(H01U), C01M(H01X),
 C01P(H01Z), C01Y(H3), C01Z(H4), C025(H025), C4(H4A)
7.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00J(H00J), C00K(H00K), C00Y(H00Y), C018(H018), C019(H019),
 C01F(H01Q), C01J(H01V), C01K(H01W), C029(H029), C02A(H02M), C02B(H02N),
 C02G(H02U), C036(H036), C038(H038), C03A(H03D), C16(H16), C9(H9A), C2(H2A),
 C3(H3A), C16A(H16A), C3A(H3AA), C9A(H9AA), C2A(H2AA), C03B(H03E), C0(H0),
 C8(H8A), C10(H10A), C13(H13)
7.c Idealised Me refined as rotating group:
 C012(H01A,H01B,H01C), C013(H01D,H01E,H01F), C014(H01G,H01H,H01I), C01A(H01J,
 H01K,H01L), C01G(H01R,H01S,H01T), C01T(H01,H,HA), C01W(H1,HB,HC), C020(H02A,
 H02B,H02C), C023(H02G,H02H,H02I), C028(H02J,H02K,H02L), C02C(H02O,H02P,H02Q),
 C02F(H02R,H02S,H02T), C02I(H02V,H02W,H02X), C02K(H02Y,HD,HE), C02L(H02Z,HF,HG),
  C02R(H5,HH,HI), C02T(H6,HJ,HK), C02U(H7,HL,HM), C02W(H8,HN,HO), C02X(H9,HP,
 HQ), C02Z(H10,HR,HS), C031(H03A,H03B,H03C)
;
_shelx_res_checksum              64167
_shelx_hkl_checksum              66485
_olex2_submission_special_instructions 'No special instructions were received'