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_4134740
_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         'C56 H54'
_chemical_formula_sum            'C56 H54'
_chemical_formula_weight         726.99
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-17
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   28.313(2)
_cell_length_b                   18.0423(9)
_cell_length_c                   8.0929(4)
_cell_measurement_reflns_used    4214
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.7780
_cell_measurement_theta_min      2.4580
_cell_volume                     4134.1(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -20.00  75.00   0.50   14.00    --   46.95 -89.00-134.00  190
  2  \w     45.00  71.00   0.50   33.00    --  107.75 -61.00-120.00   52
  3  \w     47.00 104.00   0.50   33.00    --  107.75 -94.00-180.00  114
  4  \w     65.00 106.00   0.50   33.00    --  107.75 -77.00 -60.00   82
  5  \w     71.00 103.00   0.50   33.00    --  107.75 -77.00   0.00   64
  6  \w     79.00 105.00   0.50   33.00    --  107.75 -77.00  30.00   52
  7  \w     35.00  71.00   0.50   33.00    --  107.75 -61.00  60.00   72
  8  \w     41.00  69.00   0.50   33.00    --  107.75 -61.00  90.00   56
  9  \w     39.00  71.00   0.50   33.00    --  107.75 -77.00 150.00   64
 10  \w     40.00  71.00   0.50   33.00    --  107.75 -61.00 120.00   62
 11  \w     43.00  69.00   0.50   33.00    --  107.75 -77.00 120.00   52
 12  \w     40.00  65.00   0.50   33.00    --  107.75 -61.00  30.00   50
 13  \w    102.00 162.00   0.50   33.00    --  107.75  89.00 -18.00  120
 14  \w    139.00 175.00   0.50   33.00    --  107.75 125.00  60.00   72
 15  \w     98.00 168.00   0.50   33.00    --  107.75 125.00 150.00  140
 16  \w     98.00 136.00   0.50   33.00    --  107.75 125.00  60.00   76
 17  \w    -50.00 -23.00   0.50   33.00    --  -86.25  45.00-180.00   54
 18  \w    -75.00  26.00   0.50   14.00    --  -46.95  89.00 -18.00  202
 19  \w    -70.00 -45.00   0.50   33.00    --  -86.25  89.00 -18.00   50
 20  \w   -143.00-118.00   0.50   33.00    --  -86.25 -89.00-134.00   50
 21  \w   -117.00 -78.00   0.50   14.00    --  -46.95-125.00  30.00   78
 22  \w   -117.00 -73.00   0.50   14.00    --  -46.95-125.00  90.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0129481000
_diffrn_orient_matrix_UB_12      0.0593557000
_diffrn_orient_matrix_UB_13      -0.1292028000
_diffrn_orient_matrix_UB_21      -0.0470296000
_diffrn_orient_matrix_UB_22      -0.0142839000
_diffrn_orient_matrix_UB_23      -0.0902725000
_diffrn_orient_matrix_UB_31      -0.0240758000
_diffrn_orient_matrix_UB_32      0.0596677000
_diffrn_orient_matrix_UB_33      0.1068643000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            23739
_diffrn_reflns_point_group_measured_fraction_full 0.809
_diffrn_reflns_point_group_measured_fraction_max 0.770
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.854
_diffrn_reflns_theta_min         2.904
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.491
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.650
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_description       needle
_exptl_crystal_F_000             1560
_exptl_crystal_size_max          0.234
_exptl_crystal_size_mid          0.026
_exptl_crystal_size_min          0.024
_refine_diff_density_max         0.637
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.124
_refine_ls_abs_structure_details
;
 Flack x determined using 1249 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.465
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     517
_refine_ls_number_reflns         6876
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.465
_refine_ls_R_factor_all          0.1530
_refine_ls_R_factor_gt           0.1389
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3553
_refine_ls_wR_factor_ref         0.3662
_reflns_Friedel_coverage         0.485
_reflns_Friedel_fraction_full    0.589
_reflns_Friedel_fraction_max     0.543
_reflns_number_gt                5747
_reflns_number_total             6876
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            10_double_periannulations.cif
_cod_data_source_block           20200115-1
_cod_original_cell_volume        4134.2(4)
_cod_database_code               4134740
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C56H54
_chemical_oxdiff_usercomment     '150 K '
_reflns_odcompleteness_completeness 99.16
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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:
 C6(H6), C7(H7), C10(H10), C13(H13), C14(H14), C16(H16), C22(H22), C27(H27),
 C28(H28), C32(H32), C33(H33), C34(H34), C38(H38), C39(H39), C45(H45), C49(H49),
  C50(H50), C52(H52)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C18(H18A,H18B,H18C),
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C42(H42A,H42B,H42C), C43(H43A,H43B,
 H43C), C44(H44A,H44B,H44C), C54(H54A,H54B,H54C), C55(H55A,H55B,H55C), C56(H56A,
 H56B,H56C)
;
_shelx_res_checksum              18959
_shelx_hkl_checksum              14976
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.557
_oxdiff_exptl_absorpt_empirical_full_min 0.700