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_7159093
_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         'C37 H30 O4'
_chemical_formula_sum            'C37 H30 O4'
_chemical_formula_weight         538.61
_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                63.593(6)
_cell_angle_beta                 77.553(7)
_cell_angle_gamma                72.143(7)
_cell_formula_units_Z            2
_cell_length_a                   10.912(5)
_cell_length_b                   13.188(6)
_cell_length_c                   13.432(7)
_cell_measurement_reflns_used    2781
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      21.130
_cell_measurement_theta_min      2.271
_cell_volume                     1640.8(14)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker SMART APEX II 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_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0552
_diffrn_reflns_av_unetI/netI     0.0842
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19515
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.544
_diffrn_reflns_theta_min         1.700
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6402
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1069 before and 0.0567 after correction. The Ratio of minimum to maximum transmission is 0.8586. 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    1.090
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_recrystallization_method
'The crystals were growth by means of evaporation of a mixture of n-hexane and toluene at RT.'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.017(3)
_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   0.931
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         7421
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.931
_refine_ls_R_factor_all          0.1313
_refine_ls_R_factor_gt           0.0642
_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^)+(0.1103P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1768
_refine_ls_wR_factor_ref         0.2149
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3414
_reflns_number_total             7421
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02046g2.cif
_cod_data_source_block           220619c_0m_a
_cod_depositor_comments
'Adding full bibliography for 7159093--7159096.cif.'
_cod_database_code               7159093
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.985
_exptl_crystal_mounting_method
'The title complex was mounted in a sealed capillary.'
_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.a Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C33(H33A,H33B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C6(H6), C4(H4), C7(H7), C3(H3), C25(H25), C21(H21), C26(H26),
 C19(H19), C20(H20), C28(H28), C29(H29), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C), C1(H1A,H1B,H1C), C36(H36A,H36B,H36C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              36616
_shelx_fab_checksum              26070
_olex2_submission_special_instructions 'No special instructions were received'