Fused diethynylbenzenes and phenanthrenes <i>via</i> arynes with alkynylsilanes.
Dong, Jie; Lei, Yu; Hu, Qiong; Zong, Lingli; Zhang, Ke; Zhang, Yajuan; Hu, Yimin; Organic & biomolecular chemistry 21 (2023) 2715–2719; doi:10.1039/d2ob02046g

data_7159094
_publ_section_title
;
 Fused diethynylbenzenes and phenanthrenes <i>via</i> arynes with
 alkynylsilanes.
;
_journal_issue                   13
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2715
_journal_page_last               2719
_journal_paper_doi               10.1039/d2ob02046g
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C32 H39 N O2 S Si'
_chemical_formula_sum            'C32 H39 N O2 S Si'
_chemical_formula_weight         529.79
_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             2022-05-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-09-22 deposited with the CCDC.	2023-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                89.032(2)
_cell_angle_beta                 77.087(2)
_cell_angle_gamma                80.029(2)
_cell_formula_units_Z            2
_cell_length_a                   10.1230(6)
_cell_length_b                   11.5763(8)
_cell_length_c                   14.0706(9)
_cell_measurement_reflns_used    9948
_cell_measurement_temperature    298.0
_cell_measurement_theta_max      24.459
_cell_measurement_theta_min      2.687
_cell_volume                     1582.51(18)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0889
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            61543
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.522
_diffrn_reflns_theta_min         2.687
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7039
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0835 before and 0.0619 after correction. The Ratio of minimum to maximum transmission is 0.9441. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.112
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         7244
_refine_ls_number_restraints     188
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1248
_refine_ls_R_factor_gt           0.0653
_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^)+(0.1053P)^2^+0.4251P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1711
_refine_ls_wR_factor_ref         0.2137
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3986
_reflns_number_total             7244
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02046g2.cif
_cod_data_source_block           20220525a
_cod_depositor_comments
'Adding full bibliography for 7159093--7159096.cif.'
_cod_database_code               7159094
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.969
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C30-C29 = C32-C30 = C32-C31
 1.54 with sigma of 0.01
 C30A-C29 = C32A-C30A = C32A-C31A
 1.54 with sigma of 0.01
 C30-C31 = C30A-C31A
 2.515 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C30 \\sim C31 \\sim C32 \\sim C30A \\sim C32A \\sim C31A: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02
C20 \\sim C21A \\sim C21 \\sim C22A \\sim C22 \\sim C20A: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C21A) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C20A) \\sim Ueq, Uanis(C22)
\\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C22A) \\sim Ueq, Uanis(C19) \\sim Ueq:
with sigma of 0.003 and sigma for terminal atoms of 0.006
4. Rigid body (RIGU) restrains
 C29, C30, C32, C31
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C29, C30A, C32A, C31A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C21, Si1, C20, C22
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C22A, Si1, C20A, C21A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
5. Others
 Sof(H29C)=Sof(H29D)=Sof(C30A)=Sof(H30C)=Sof(H30D)=Sof(C32A)=Sof(H32C)=
 Sof(H32D)=Sof(C31A)=Sof(H31D)=Sof(H31E)=Sof(H31F)=1-FVAR(1)
 Sof(H29A)=Sof(H29B)=Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(C31)=Sof(H31A)=Sof(H31B)=
 Sof(H31C)=Sof(C32)=Sof(H32A)=Sof(H32B)=FVAR(1)
 Sof(C20A)=Sof(H20D)=Sof(H20E)=Sof(H20F)=Sof(C21A)=Sof(H21D)=Sof(H21E)=
 Sof(H21F)=Sof(C22A)=Sof(H22D)=Sof(H22E)=Sof(H22F)=1-FVAR(2)
 Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=
 Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H22C)=FVAR(2)
 Fixed Y: C31A(0.919539)
 Fixed Z: C31A(0.22623)
6.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C8(H8A,H8B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B),
 C29(H29A,H29B), C29(H29C,H29D), C30(H30A,H30B), C32(H32A,H32B), C30A(H30C,
 H30D), C32A(H32C,H32D)
6.b Me refined with riding coordinates:
 C22A(H22D,H22E,H22F)
6.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C10(H10), C11(H11), C13(H13), C14(H14)
6.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C), C26(H26A,H26B,H26C), C31(H31A,H31B,H31C), C31A(H31D,H31E,H31F),
 C20A(H20D,H20E,H20F), C21A(H21D,H21E,H21F)
;
_shelx_res_checksum              95252
_olex2_submission_special_instructions 'No special instructions were received'