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_4134738
_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         '0.05(C56 H32 I4)'
_chemical_formula_sum            'C2.6 H1.49 I0.19'
_chemical_formula_weight         56.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_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                90
_cell_angle_beta                 98.8238(10)
_cell_angle_gamma                90
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_cell_length_a                   8.8782(4)
_cell_length_b                   23.1887(11)
_cell_length_c                   22.1751(11)
_cell_measurement_reflns_used    9783
_cell_measurement_temperature    127(2)
_cell_measurement_theta_max      34.097
_cell_measurement_theta_min      2.365
_cell_volume                     4511.2(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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      127.43
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.954
_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  0.0382
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            101777
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.188
_diffrn_reflns_theta_min         2.365
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.800
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_correction_T_min  0.7001
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0637 before and 0.0506 after correction.
The Ratio of minimum to maximum transmission is 0.9373.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'pale pink'
_exptl_crystal_density_diffrn    1.785
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular plate'
_exptl_crystal_F_000             2320
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.025
_refine_diff_density_min         -0.699
_refine_diff_density_rms         0.154
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         19244
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0337
_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^)+(0.0272P)^2^+5.1332P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0664
_refine_ls_wR_factor_ref         0.0744
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14927
_reflns_number_total             19244
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            3b_double_periannulations.cif
_cod_data_source_block           eg126
_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        'C2.60 H1.49 I0.19'
_cod_database_code               4134738
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2AA(H2AA), C4AA(H4AA), C8AA(H8AA), C9CA(H9CA), C2DA(H2DA), C4DA(H4DA),
 C8BA(H8BA), C9BA(H9BA), C1CA(H1CA), C2CA(H2CA), C5CA(H5CA), C6CA(H6CA),
 C8CA(H8CA), C2FA(H2FA), C3FA(H3FA), C7DA(H7DA), C8DA(H8DA), C0EA(H0EA),
 C1EA(H1EA), C4EA(H4EA), C7EA(H7EA), C0DA(H0DA), C1DA(H1DA), C9DA(H9DA),
 C2EA(H2EA), C6EA(H6EA), C5(H5), C8(H8), C10(H10), C12(H12), C13(H13), C14(H14)
;
_shelx_res_checksum              9828
_shelx_hkl_checksum              94337
_shelx_fab_checksum              93405
_olex2_submission_special_instructions 'No special instructions were received'