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_4134742
_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         'C30 H20 I2 O2'
_chemical_formula_sum            'C30 H20 I2 O2'
_chemical_formula_weight         666.30
_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             2018-02-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                64.033(3)
_cell_angle_beta                 69.797(2)
_cell_angle_gamma                67.014(2)
_cell_formula_units_Z            6
_cell_length_a                   14.5262(12)
_cell_length_b                   17.6511(16)
_cell_length_c                   18.1360(16)
_cell_measurement_reflns_used    9605
_cell_measurement_temperature    273(2)
_cell_volume                     3762.4(6)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      273.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_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  0.1321
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            284538
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         2.213
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    11.365
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6058
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1041 before and 0.0738 after correction.
The Ratio of minimum to maximum transmission is 0.8129.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    3.785
_exptl_crystal_F_000             3740
_refine_diff_density_max         1.182
_refine_diff_density_min         -0.795
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     914
_refine_ls_number_reflns         13866
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.1303
_refine_ls_R_factor_gt           0.0681
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0183P)^2^+28.9460P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1367
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8086
_reflns_number_total             13866
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            3d_double_periannulations.cif
_cod_data_source_block           try1_roomtemp
_cod_depositor_comments
;

2025-09-07
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C H I O'
_cod_original_formula_weight         155.92
_cod_original_formula_moiety
'0.04(C30 H20 I2 O2), 0.04(C29 H17 I2 O2), 0.04(C30 H17 I2 O2)'
_cod_original_formula_units_Z            55
_cod_database_code               4134742
_shelx_shelxl_version_number     2017/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00R(H00R), C00S(H00S), C00W(H00W), C00Y(H00Y), C010(H010),
 C011(H011), C013(H013), C015(H015), C018(H018), C01A(H01A), C01B(H01B),
 C01G(H01G), C01L(H01L), C01N(H01N), C01O(H01O), C01P(H01P), C01Q(H01Q),
 C01R(H01R), C01S(H01S), C01T(H01T), C01U(H01U), C01W(H01W), C01X(H01X),
 C01Y(H01Y), C022(H022), C023(H023), C024(H024), C027(H027), C028(H028),
 C02A(H02P), C02D(H02Q), C02E(H02R), C02F(H02H), C02G(H02G), C02H(H02I),
 C02J(H02S), C02K(H02K), C02L(H02L), C02M(H02M), C02N(H02T), C02P(H02U)
2.b Idealised Me refined as rotating group:
 C02O(H02J,H02N,H02O), C02Q(H02A,H02B,H02C), C02R(H02D,H02E,H02F), C02S(H02V,
 H02W,H02X)
;
_shelx_res_checksum              45020
_shelx_hkl_checksum              26558
_olex2_submission_special_instructions 'No special instructions were received'