Pyrylenes: A New Class of Tunable, Redox-Switchable, Photoexcitable Pyrylium-Carbene Hybrids with Three Stable Redox-States.
Antoni, Patrick W.; Hansmann, Max M.; Journal of the American Chemical Society 140 (2018) 14823–14835; doi:10.1021/jacs.8b08545

data_4133123
_publ_section_title
;
 Pyrylenes: A New Class of Tunable, Redox-Switchable, Photoexcitable
 Pyrylium-Carbene Hybrids with Three Stable Redox-States.
;
_journal_issue                   44
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14823
_journal_page_last               14835
_journal_paper_doi               10.1021/jacs.8b08545
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C34 H46 N2 O'
_chemical_formula_sum            'C34 H46 N2 O'
_chemical_formula_weight         498.73
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.701(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.9545(14)
_cell_length_b                   8.8519(9)
_cell_length_c                   20.4216(19)
_cell_measurement_reflns_used    1438
_cell_measurement_temperature    150.02
_cell_measurement_theta_max      26.55
_cell_measurement_theta_min      2.60
_cell_volume                     3043.9(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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.02
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_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  0.0299
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            111804
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.547
_diffrn_reflns_theta_min         2.220
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  0.9144
_exptl_absorpt_correction_T_min  0.8560
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0639 before and 0.0454 after correction. The Ratio of minimum to maximum transmission is 0.9361. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.088
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of thf and pentane  by slow evaporation'
_exptl_crystal_size_max          0.401
_exptl_crystal_size_mid          0.308
_exptl_crystal_size_min          0.205
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         10119
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0492
_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^)+(0.0675P)^2^+0.8086P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1427
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8691
_reflns_number_total             10119
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b08545_si_004.cif
_cod_data_source_block           2btBu
_cod_database_code               4133123
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.975
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C26-H26A = C26-H26B = C25-H25B = C25-H25A
 0.98 with sigma of 0.02
3. Others
 Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=1-FVAR(1)
 Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C18(H18), C20(H20), C29(H29), C31(H31)
4.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C12(H12A,H12B,H12C),
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C22(H22A,H22B,
 H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C33(H33A,H33B,H33C), C34(H34A,
 H34B,H34C), C35(H35A,H35B,H35C)
;
_shelx_res_checksum              99905
_shelx_hkl_checksum              9955
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 800'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_special_instructions 'No special instructions were received'