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_4133119
_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         'F6 Sb, C35 H55 N O'
_chemical_formula_sum            'C35 H55 F6 N O Sb'
_chemical_formula_weight         741.55
_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             2018-06-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.7390(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.3993(4)
_cell_length_b                   10.4714(3)
_cell_length_c                   21.8940(6)
_cell_measurement_reflns_used    9705
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      22.93
_cell_measurement_theta_min      2.58
_cell_volume                     3560.42(17)
_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      100.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56086
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            79491
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         25.165
_diffrn_reflns_theta_min         2.492
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.448
_exptl_absorpt_correction_T_max  0.5245
_exptl_absorpt_correction_T_min  0.4503
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0767 before and 0.0616 after correction. The Ratio of minimum to maximum transmission is 0.8585. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       block
_exptl_crystal_F_000             1540
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         2.699
_refine_diff_density_min         -1.009
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     457
_refine_ls_number_reflns         12963
_refine_ls_number_restraints     141
_refine_ls_restrained_S_all      1.179
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0527
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0538P)^2^+5.4582P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1283
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11330
_reflns_number_total             12963
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b08545_si_009.cif
_cod_data_source_block           3ctBu
_cod_database_code               4133119
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.916
_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
 F8-F9
 2.64 with sigma of 0.02
 F9-F10
 2.64 with sigma of 0.02
 F10-F7
 2.64 with sigma of 0.02
 F7-F8
 2.64 with sigma of 0.02
 F8-F2
 2.64 with sigma of 0.02
 F9-F2
 2.64 with sigma of 0.02
 F2-F10
 2.64 with sigma of 0.02
 F7-F2
 2.64 with sigma of 0.02
 F9-F1
 2.64 with sigma of 0.02
 F10-F1
 2.64 with sigma of 0.02
 F7-F1
 2.64 with sigma of 0.02
 F1-F8
 2.64 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(Sb2) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.001
4. Rigid body (RIGU) restrains
 Sb1, F2, F1, F3, F4, F6, F5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F2, F1, F8, F9, F10, F7, Sb2
 with sigma for 1-2 distances of 0.0005 and sigma for 1-3 distances of 0.0005
5. Others
 Sof(F8)=Sof(F9)=Sof(F10)=Sof(F7)=Sof(Sb2)=1-FVAR(1)
 Sof(Sb1)=Sof(F3)=Sof(F4)=Sof(F6)=Sof(F5)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C33(H33), C30(H30)
6.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C12(H12A,H12B), C16(H16A,H16B)
6.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C2(H2), C28(H28), C26(H26), C27(H27)
6.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C22(H22A,H22B,H22C), C7(H7A,H7B,
 H7C), C9(H9A,H9B,H9C), C31(H31A,H31B,H31C), C8(H8A,H8B,H8C), C34(H34A,H34B,
 H34C), C32(H32A,H32B,H32C), C35(H35A,H35B,H35C), C19(H19A,H19B,H19C), C14(H14A,
 H14B,H14C), C17(H17A,H17B,H17C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              2301
_shelx_hkl_checksum              7017
_olex2_submission_special_instructions 'No special instructions were received'