Visible-light-induced direct C-H alkylation of polycyclic aromatic hydrocarbons with alkylsulfones.
Ohtsuka, Motoo; Ghosh, Koushik; Yim, Jacky C.-H.; Sotome, Hikaru; Okamoto, Tsubasa; Suda, Kayo; Kobori, Yasuhiro; Yokogawa, Daisuke; Miyasaka, Hiroshi; Crudden, Cathleen M.; Nambo, Masakazu; Chemical science 15 (2024) 10592–10599; doi:10.1039/d4sc02577f

data_1571786
_publ_section_title
;
 Visible-light-induced direct C-H alkylation of polycyclic aromatic
 hydrocarbons with alkylsulfones.
;
_journal_issue                   27
_journal_name_full               'Chemical science'
_journal_page_first              10592
_journal_page_last               10599
_journal_paper_doi               10.1039/d4sc02577f
_journal_volume                  15
_journal_year                    2024
_chemical_formula_sum            'C28 H34'
_chemical_formula_weight         370.55
_chemical_name_systematic        1,3,7-Tri-tert-butylpyrene
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     SHELXT
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-12-07 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.148(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.5389(12)
_cell_length_b                   28.047(4)
_cell_length_c                   16.886(2)
_cell_measurement_reflns_used    3353
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.1
_cell_volume                     4460.2(10)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Pilatus 200K'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_av_unetI/netI     0.0807
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            33500
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         3.070
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.104
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 2162 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         8275
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.970
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0461
_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^)+(0.0450P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0973
_reflns_Friedel_coverage         0.990
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                5669
_reflns_number_total             8275
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc02577f2.cif
_cod_data_source_block           ydkr
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1571786.cif.
;
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               1571786
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.994
_shelx_estimated_absorpt_t_max   0.999
_shelx_res_checksum              71941