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_7159095
_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         'C42 H46 O4 Si'
_chemical_formula_sum            'C42 H46 O4 Si'
_chemical_formula_weight         642.88
_chemical_name_systematic        8a-ok
_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             2022-11-28
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-11-28 deposited with the CCDC.	2023-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                111.575(2)
_cell_angle_beta                 96.279(2)
_cell_angle_gamma                102.106(2)
_cell_formula_units_Z            2
_cell_length_a                   11.5700(8)
_cell_length_b                   12.6302(8)
_cell_length_c                   15.0893(10)
_cell_measurement_reflns_used    9897
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      24.35
_cell_measurement_theta_min      2.59
_cell_volume                     1962.3(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker D8 Venture diffractrometer'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      300.00
_diffrn_detector                 'CCD area detector'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0829
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            51981
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.675
_diffrn_reflns_theta_min         2.589
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0978 before and 0.0548 after correction.
The Ratio of minimum to maximum transmission is 0.8914.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.088
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     551
_refine_ls_number_reflns         8909
_refine_ls_number_restraints     600
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.1182
_refine_ls_R_factor_gt           0.0598
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0944P)^2^+0.2023P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1584
_refine_ls_wR_factor_ref         0.1923
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4892
_reflns_number_total             8909
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02046g2.cif
_cod_data_source_block           mo_20211227d_0m_a
_cod_depositor_comments
'Adding full bibliography for 7159093--7159096.cif.'
_cod_database_code               7159095
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.978
_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
 C34-C35
 1.45 with sigma of 0.002
 C35A-C34A = C35-C34
 1.54 with sigma of 0.01
 C27A-C26A = C27-C26
 1.54 with sigma of 0.01
 C3-C2 = C2A-C1A = C2-C1 = C3A-C2A
 1.54 with sigma of 0.01
 C3A-C1A = C3-C1
 2.515 with sigma of 0.02
 C26-C23 \\sim C26A-C23
 with sigma of 0.02
3. Rigid bond restraints
 C1, C2, C3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3: within 2A with sigma of 0.01 and sigma for terminal atoms
of 0.02 within 2A
C27 \\sim C26: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
C28 \\sim C29 \\sim C30 \\sim C31 \\sim C32 \\sim C33 \\sim C34 \\sim C35 \\sim
C28A \\sim C29A \\sim C30A \\sim C31A \\sim C32A \\sim C33A \\sim C34A \\sim
C35A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within
2A
C27A \\sim C26 \\sim C26A \\sim C27: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
C1 \\sim C2 \\sim C3 \\sim O2 \\sim O2A \\sim C2A \\sim C3A \\sim C1A \\sim O1A
\\sim O1: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 C34, C28, C30, C35, C29, C32, C31, C33, C13
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C32A, C30A, C29A, C33A, C31A, C28A, C35A, C13
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C23, C26, C27
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C23, C26A, C27A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C2, C3, C9, O1, O2, C1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C9, O2A, O1A, C2A, C3A, C1A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
6. Others
 Sof(C28A)=Sof(C29A)=Sof(H29A)=Sof(C30A)=Sof(H30A)=Sof(C31A)=Sof(C32A)=
 Sof(H32A)=Sof(C33A)=Sof(H33A)=Sof(C34A)=Sof(H34C)=Sof(H34D)=Sof(C35A)=
 Sof(H35D)=Sof(H35E)=Sof(H35F)=1-FVAR(1)
 Sof(C28)=Sof(C29)=Sof(H29)=Sof(C30)=Sof(H30)=Sof(C31)=Sof(C32)=Sof(H32)=
 Sof(C33)=Sof(H33)=Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(C35)=Sof(H35A)=Sof(H35B)=
 Sof(H35C)=FVAR(1)
 Sof(C26A)=Sof(H26C)=Sof(H26D)=Sof(C27A)=Sof(H27D)=Sof(H27E)=Sof(H27F)=1-FVAR(2)
 Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(H27C)=FVAR(2)
 Sof(O2A)=Sof(O1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=1-FVAR(3)
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3A)=Sof(H3B)=
 Sof(H3C)=Sof(O1)=Sof(O2)=FVAR(3)
7.a Ternary CH refined with riding coordinates:
 C2(H2), C5(H5), C2A(H2A)
7.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C17(H17A,H17B), C26(H26A,H26B), C34(H34A,H34B), C34A(H34C,
 H34D), C26A(H26C,H26D)
7.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C21(H21), C22(H22), C24(H24), C25(H25), C29(H29), C30(H30),
 C32(H32), C33(H33), C29A(H29A), C30A(H30A), C32A(H32A), C33A(H33A)
7.d Fitted hexagon refined as free rotating group:
 C28(C29,C30,C31,C32,C33), C28A(C29A,C30A,C31A,C32A,C33A)
7.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C6(H6A,H6B,H6C), C27(H27A,
 H27B,H27C), C35(H35A,H35B,H35C), C40(H40A,H40B,H40C), C41(H41A,H41B,H41C),
 C42(H42A,H42B,H42C), C35A(H35D,H35E,H35F), C27A(H27D,H27E,H27F), C3A(H3AA,H3AB,
 H3AC), C1A(H1AA,H1AB,H1AC)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              2906
_shelx_fab_checksum              84228
_olex2_submission_special_instructions 'No special instructions were received'