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_4134741
_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         '0.07(C36 H20 I1.98)'
_chemical_formula_sum            'C2.53 H1.4 I0.14'
_chemical_formula_weight         49.34
_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             2017-05-31
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                99.0899(13)
_cell_angle_beta                 90.1300(14)
_cell_angle_gamma                90.1473(13)
_cell_formula_units_Z            57
_cell_length_a                   9.1268(7)
_cell_length_b                   18.1759(13)
_cell_length_c                   18.2510(13)
_cell_measurement_reflns_used    9879
_cell_measurement_temperature    128(2)
_cell_measurement_theta_max      34.001
_cell_measurement_theta_min      2.365
_cell_volume                     2989.6(4)
_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    'SIR2004 (Burla et al., 2007)'
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_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.0494
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            54086
_diffrn_reflns_point_group_measured_fraction_full 0.999
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.110
_diffrn_reflns_theta_min         2.231
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.100
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6495
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0757 before and 0.0493 after correction.
The Ratio of minimum to maximum transmission is 0.8706.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular plate'
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_exptl_crystal_size_min          0.02
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_refine_diff_density_rms         0.139
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.1148
_refine_ls_R_factor_gt           0.0709
_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^)+(0.0370P)^2^+21.5180P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1449
_refine_ls_wR_factor_ref         0.1603
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10994
_reflns_number_total             17568
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            3c_double_periannulations.cif
_cod_data_source_block           eg142triclinic
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'NA' 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_original_formula_sum        'C2.53 H1.40 I0.14'
_cod_database_code               4134741
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: I1(0.97786) I2A(0.9) I2B(0.1) I3A(0.9) I3B(0.1) I4(0.97263)
3.a Aromatic/amide H refined with riding coordinates:
 C0DA(H0DA), C0FA(H0FA), C0HA(H0HA), C1EA(H1EA), C1GA(H1GA), C1(H1),
 C2BA(H2BA), C2DA(H2DA), C2EA(H2EA), C2GA(H2GA), C2HA(H2HA), C2(H2), C3DA(H3DA),
  C3CA(H3CA), C3GA(H3GA), C4DA(H4DA), C4CA(H4CA), C4FA(H4FA), C4GA(H4GA),
 C5CA(H5CA), C5FA(H5FA), C5HA(H5HA), C5GA(H5GA), C6DA(H6DA), C6CA(H6CA),
 C6EA(H6EA), C6GA(H6GA), C7AA(H7AA), C7DA(H7DA), C7FA(H7FA), C7EA(H7EA),
 C7GA(H7GA), C8DA(H8DA), C8FA(H8FA), C8EA(H8EA), C8HA(H8HA), C8GA(H8GA),
 C9CA(H9CA), C9HA(H9HA), C9GA(H9GA)
;
_shelx_res_checksum              71488
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_shelx_fab_checksum              62951
_olex2_submission_special_instructions 'No special instructions were received'