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_4134739
_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 H14 I2 N2, C H Cl3'
_chemical_formula_sum            'C31 H15 Cl3 I2 N2'
_chemical_formula_weight         775.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-08-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.467(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8601(13)
_cell_length_b                   20.375(2)
_cell_length_c                   11.4044(12)
_cell_measurement_reflns_used    9978
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      29.76
_cell_measurement_theta_min      2.31
_cell_volume                     2834.4(5)
_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      273.15
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.975
_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  0.0564
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            79377
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.799
_diffrn_reflns_theta_min         2.311
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.526
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0919 before and 0.0616 after correction.
The Ratio of minimum to maximum transmission is 0.8713.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.892
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular block'
_exptl_crystal_F_000             1601
_exptl_crystal_size_max          0.85
_exptl_crystal_size_mid          0.64
_exptl_crystal_size_min          0.44
_refine_diff_density_max         1.190
_refine_diff_density_min         -0.669
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         7908
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0523
_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^)+(0.0338P)^2^+10.4825P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1305
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5224
_reflns_number_total             7908
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            3e_double_periannulations.cif
_cod_data_source_block           try1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' 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               4134739
_shelx_shelxl_version_number     2017/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C19(H19)
2.b Aromatic/amide H refined with riding coordinates:
 C6BA(H6BA), C8BA(H8BA), C2AA(H2AA), C5AA(H5AA), C7AA(H7AA), C8AA(H8AA),
 C0BA(H0BA), C6(H6), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14), C16(H16)
;
_shelx_res_checksum              61052
_shelx_hkl_checksum              1793
_olex2_submission_special_instructions 'No special instructions were received'