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_4134737
_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         'C32 H18 I2'
_chemical_formula_sum            'C32 H18 I2'
_chemical_formula_weight         656.26
_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   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                102.391(3)
_cell_angle_beta                 99.151(3)
_cell_angle_gamma                115.642(2)
_cell_formula_units_Z            2
_cell_length_a                   9.2973(10)
_cell_length_b                   10.4393(11)
_cell_length_c                   15.0098(15)
_cell_measurement_reflns_used    6681
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.494
_cell_measurement_theta_min      2.281
_cell_volume                     1229.1(2)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_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  0.0419
_diffrn_reflns_av_unetI/netI     0.0999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18895
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.767
_diffrn_reflns_theta_min         2.282
_exptl_absorpt_coefficient_mu    2.577
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1167 before and 0.0573 after correction.
The Ratio of minimum to maximum transmission is 0.9179.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.773
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.13
_refine_diff_density_max         1.103
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.111
_refine_ls_abs_structure_details
;
 Flack x determined using 2317 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.032(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     613
_refine_ls_number_reflns         11174
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1308
_refine_ls_R_factor_gt           0.0654
_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^)+(0.0300P)^2^+0.5170P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.1056
_reflns_Friedel_coverage         0.942
_reflns_Friedel_fraction_full    0.962
_reflns_Friedel_fraction_max     0.935
_reflns_number_gt                6759
_reflns_number_total             11174
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            3f'_double_periannulations.cif
_cod_data_source_block           nik_chi_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 

2025-07-29
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C32 H18 I2)'
_cod_original_formula_sum        'C64 H36 I4'
_cod_original_formula_units_Z    1
_cod_original_formula_weight     1312.53
_cod_database_code               4134737
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   33.855
_shelx_estimated_absorpt_t_min   2.289
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5C(H008), C20C(H009), C60C(H00P), C41C(H00R), C10C(H00S), C53C(H00T),
 C50C(H00V), C43C(H00W), C11C(H010), C54C(H013), C64C(H015), C56C(H016),
 C44C(H017), C31C(H018), C21C(H019), C4C(H01A), C47C(H01B), C12C(H01D),
 C29C(H01E), C24C(H01F), C30C(H01G), C33C(H01H), C28C(H01I), C14C(H01K),
 C36C(H01L), C63C(H01M), C35C(H01N), C2C(H01O), C37C(H01P), C62C(H01Q),
 C1C(H01R), C34C(H01S), C25C(H01T), C32C(H01U), C61C(H01V), C3C(H01W)
;
_shelx_res_checksum              25640
_shelx_hkl_checksum              63909
_olex2_submission_special_instructions 'No special instructions were received'