Triflic Acid-Promoted Adamantylation and <i>tert</i>-Butylation of Pyrene: Fluorescent Properties of Pyrene-Decorated Adamantanes and a Channeled Crystal Structure of 1,3,5-Tris(pyren-2-yl)adamantane.
Wrona-Piotrowicz, Anna; Makal, Anna; Zakrzewski, Janusz; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01060

data_4038708
_publ_section_title
;
 Triflic Acid-Promoted Adamantylation and <i>tert</i>-Butylation of
 Pyrene: Fluorescent Properties of Pyrene-Decorated Adamantanes and a
 Channeled Crystal Structure of 1,3,5-Tris(pyren-2-yl)adamantane.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01060
_journal_year                    2020
_chemical_formula_moiety         'C58 H40'
_chemical_formula_sum            'C58 H40'
_chemical_formula_weight         736.90
_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             2019-06-22
_audit_creation_method
;
Olex2 1.2
(compiled May 29 2018 13:30:08 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                117.369(5)
_cell_angle_beta                 91.410(4)
_cell_angle_gamma                93.755(4)
_cell_formula_units_Z            2
_cell_length_a                   8.0569(4)
_cell_length_b                   17.1074(9)
_cell_length_c                   17.4187(9)
_cell_measurement_reflns_used    5590
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      73.8940
_cell_measurement_theta_min      2.8070
_cell_volume                     2123.5(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.43d (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43d (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43d (Rigaku OD, 2018)'
_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_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_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 -117.00 -10.00 1.00 1.00 -- -41.28 -77.00-150.00 107 2 \w -117.00 -17.00 1.00 1.00 -- -41.28 -77.00 -60.00 100 3 \w -93.00 -66.00 1.00 1.00 -- -41.28 -37.00 90.00 27 4 \w -59.00 -31.00 1.00 1.00 -- -41.28 -37.00 90.00 28 5 \w 1.00 80.00 1.00 1.00 -- 41.28 -99.00 60.00 79 6 \w 30.00 128.00 1.00 2.00 -- 106.16 -30.00 0.00 98 7 \w 133.00 174.00 1.00 2.00 -- 106.16 30.00-180.00 41 8 \w 47.00 119.00 1.00 2.00 -- 106.16 -30.00-180.00 72 9 \w 86.00 114.00 1.00 2.00 -- 106.16 30.00-180.00 28 10 \w 75.00 117.00 1.00 2.00 -- 106.16-125.00 30.00 42 11 \w 46.00 117.00 1.00 2.00 -- 106.16-125.00-150.00 71 12 \w 64.00 139.00 1.00 2.00 -- 106.16 -77.00-150.00 75 13 \w 126.00 170.00 1.00 2.00 -- 106.16 45.00-120.00 44 14 \w 80.00 121.00 1.00 2.00 -- 106.16 45.00-120.00 41 15 \w 34.00 61.00 1.00 2.00 -- 106.16-125.00 30.00 27 16 \w 26.00 101.00 1.00 2.00 -- 106.16 -94.00-150.00 75 17 \w 33.00 131.00 1.00 2.00 -- 106.16 -77.00 30.00 98 18 \w 105.00 178.00 1.00 2.00 -- 106.16 30.00 -30.00 73 19 \w 32.00 59.00 1.00 2.00 -- 106.16 -77.00 0.00 27'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0552445000
_diffrn_orient_matrix_UB_12      -0.0708290000
_diffrn_orient_matrix_UB_13      -0.0928270000
_diffrn_orient_matrix_UB_21      0.1378914000
_diffrn_orient_matrix_UB_22      0.0386252000
_diffrn_orient_matrix_UB_23      -0.0357037000
_diffrn_orient_matrix_UB_31      0.1216296000
_diffrn_orient_matrix_UB_32      -0.0620602000
_diffrn_orient_matrix_UB_33      0.0080395000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15343
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.803
_diffrn_reflns_theta_min         2.920
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.494
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.581
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.43d (Rigaku Oxford Diffraction, 2018) 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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.362
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         8342
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0811
_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^)+(0.0582P)^2^+4.7010P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1957
_refine_ls_wR_factor_ref         0.2067
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6195
_reflns_number_total             8342
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01060_si_002.cif
_cod_data_source_block           wpa603_mask
_cod_database_code               4038708
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C59 H41 Cl3'
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.842
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C14(H14), C15(H15), C17(H17), C18(H18), C19(H19), C21(H21),
 C22(H22), C24(H24), C32(H32), C34(H34), C35(H35), C37(H37), C38(H38), C39(H39),
  C41(H41), C42(H42), C44(H44), C52(H52), C54(H54), C55(H55), C57(H57),
 C58(H58), C59(H59), C61(H61), C62(H62), C64(H64)
;
_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 1.213
_oxdiff_exptl_absorpt_empirical_full_min 0.836