Twofold π-Extension of Polyarenes via Double and Triple Radical Alkyne <i>peri</i>-Annulations: Radical Cascades Converging on the Same Aromatic Core.
Gonzalez-Rodriguez, Edgar; Abdo, Miguel A.; Dos Passos Gomes, Gabriel; Ayad, Suliman; White, Frankie D.; Tsvetkov, Nikolay P.; Hanson, Kenneth; Alabugin, Igor V.; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c01856

data_4134736
_publ_section_title
;
 Twofold \p-Extension of Polyarenes via Double and Triple Radical Alkyne
 <i>peri</i>-Annulations: Radical Cascades Converging on the Same Aromatic
 Core.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c01856
_journal_year                    2020
_chemical_formula_moiety         'C56 H68 Sn2'
_chemical_formula_sum            'C56 H68 Sn2'
_chemical_formula_weight         978.52
_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     direct
_audit_creation_date             2019-02-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90.7726(14)
_cell_angle_beta                 102.0131(14)
_cell_angle_gamma                114.0745(13)
_cell_formula_units_Z            1
_cell_length_a                   10.0922(6)
_cell_length_b                   11.2174(6)
_cell_length_c                   12.9069(7)
_cell_measurement_reflns_used    4584
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.442
_cell_measurement_theta_min      2.273
_cell_volume                     1296.91(13)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      298.01
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_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  0.0524
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20016
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.546
_diffrn_reflns_theta_min         2.273
_exptl_absorpt_coefficient_mu    0.995
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction.
wR2(int) was 0.1252 before and 0.0425 after correction.
The Ratio of minimum to maximum transmission is 0.8892.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular blocks'
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.786
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         5958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.973
_refine_ls_R_factor_all          0.1558
_refine_ls_R_factor_gt           0.0646
_refine_ls_shift/su_max          0.083
_refine_ls_shift/su_mean         0.020
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1485
_refine_ls_wR_factor_ref         0.1881
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2664
_reflns_number_total             5958
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            2f'_double_periannulations.cif
_cod_data_source_block           july5_nik1_fract2_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'n/a' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4134736
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   21.445
_shelx_estimated_absorpt_t_min   2.274
_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:
 C1C(H14a,H14b), C5C(H16a,H16b), C8C(H17a,H17b), C9C(H19a,H19b), C10C(H20a,
 H20b), C2C(H3a,H3b), C11C(H8a,H8b)
2.b Aromatic/amide H refined with riding coordinates:
 C26C(H5AA), C16C(H6AA), C22C(H10), C18C(H11), C28C(H1AA), C17C(H13),
 C23C(H15), C20C(H18), C19C(H0AA), C3C(H5), C6C(H6)
2.c Idealised Me refined as rotating group:
 C4C(H7a,H7b,H7c), C7C(H9a,H9b,H9c), C12C(H12a,H12b,H12c)
;
_shelx_res_checksum              72541
_shelx_hkl_checksum              52527
_olex2_submission_special_instructions 'No special instructions were received'