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_4133116
_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         '2(F6 Sb), C H2 Cl2, C41 H40 N2 O3'
_chemical_formula_sum            'C42 H42 Cl2 F12 N2 O3 Sb2'
_chemical_formula_weight         1165.17
_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     dual
_audit_creation_date             2018-05-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_cell_angle_alpha                90
_cell_angle_beta                 113.97(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.146(10)
_cell_length_b                   10.812(5)
_cell_length_c                   21.727(14)
_cell_measurement_reflns_used    239
_cell_measurement_temperature    150.07
_cell_measurement_theta_max      26.01
_cell_measurement_theta_min      2.83
_cell_volume                     4539(4)
_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      150.07
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.979
_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  0.0616
_diffrn_reflns_av_unetI/netI     0.0982
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            26296
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.811
_diffrn_reflns_theta_min         2.052
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.398
_exptl_absorpt_correction_T_max  0.1695
_exptl_absorpt_correction_T_min  0.1192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.2033 before and 0.0451 after correction. The Ratio of minimum to maximum transmission is 0.7032. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_description       needle
_exptl_crystal_F_000             2304
_exptl_crystal_size_max          0.438
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.039
_refine_diff_density_max         0.896
_refine_diff_density_min         -1.014
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     528
_refine_ls_number_reflns         11609
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1219
_refine_ls_R_factor_gt           0.0618
_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^)+(0.0394P)^2^+5.3471P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1232
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6890
_reflns_number_total             11609
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b08545_si_011.cif
_cod_data_source_block           4dPh
_cod_database_code               4133116
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.948
_shelx_estimated_absorpt_t_min   0.580
_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.a Secondary CH2 refined with riding coordinates:
 C42(H42A,H42B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C15(H15),
 C14(H14), C18(H18), C17(H17), C16(H16), C26(H26), C28(H28), C35(H35), C37(H37)
2.c Fitted hexagon refined as free rotating group:
 C6(C7,C8,C9,C10,C5), C15(C14,C13,C18,C17,C16), C27(C26,C25,C24,C29,C28),
 C33(C34,C35,C36,C37,C38)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C30(H30A,H30B,H30C), C31(H31A,H31B,
 H31C), C32(H32A,H32B,H32C), C39(H39A,H39B,H39C), C40(H40A,H40B,H40C), C41(H41A,
 H41B,H41C)
;
_shelx_res_checksum              95791
_shelx_hkl_checksum              35007
_olex2_submission_special_instructions 'No special instructions were received'