Taming the Stilbene Radical Anion
Sieg, Grégoire; Müller, Igor; Weißer, Kilian; Werncke, Gunnar; Chemical Science  (2022) –; doi:10.1039/D2SC04451J

data_1567936
_publ_section_title
;
 Taming the Stilbene Radical Anion
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC04451J
_journal_year                    2022
_chemical_formula_moiety         'C55 H112 Fe K2 N3 O13 Si6'
_chemical_formula_sum            'C55 H112 Fe K2 N3 O13 Si6'
_chemical_formula_weight         1326.06
_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     dual
_audit_creation_date             2022-05-05
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2019.07.11 svn.r3635 for OlexSys, GUI svn.r5848)
;
_audit_update_record
;
2022-06-13 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;
_cell_angle_alpha                80.4780(10)
_cell_angle_beta                 84.3760(10)
_cell_angle_gamma                84.0040(10)
_cell_formula_units_Z            2
_cell_length_a                   10.7165(3)
_cell_length_b                   17.9760(4)
_cell_length_c                   19.6298(4)
_cell_measurement_reflns_used    9985
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.82
_cell_measurement_theta_min      2.24
_cell_volume                     3696.40(15)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL n/a (Sheldrick, 2008)'
_computing_structure_solution    'XT n/a (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.836
_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  0.0392
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.836
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            87985
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.363
_diffrn_reflns_theta_min         1.917
_exptl_absorpt_coefficient_mu    0.467
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.7100
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0866 before and 0.0504 after correction.
The Ratio of minimum to maximum transmission is 0.9512.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'dark blue'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_description       rhombohedral
_exptl_crystal_F_000             1430
_exptl_crystal_size_max          0.519
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.656
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     902
_refine_ls_number_reflns         22101
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0482P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0918
_reflns_Friedel_coverage         0.000
_reflns_number_gt                16122
_reflns_number_total             22101
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc04451j2.cif
_cod_data_source_block           2
_cod_database_code               1567936
_shelx_shelxl_version_number     2016/6
_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
 K2-O8 \\sim K2-O14
 with sigma of 0.04
 K2-O9 \\sim K2-O15
 with sigma of 0.04
 K2-O10 \\sim K2-O16
 with sigma of 0.04
 K2-O11 \\sim K2-O17
 with sigma of 0.04
 K2-O12 \\sim K2-O18
 with sigma of 0.04
 K2-O13 \\sim K2-O19
 with sigma of 0.04
 K2-C44 \\sim K2-C56
 with sigma of 0.04
 K2-C45 \\sim K2-C57
 with sigma of 0.04
 K2-C46 \\sim K2-C58
 with sigma of 0.04
 K2-C47 \\sim K2-C59
 with sigma of 0.04
 K2-C48 \\sim K2-C60
 with sigma of 0.04
 K2-C49 \\sim K2-C61
 with sigma of 0.04
 K2-C50 \\sim K2-C62
 with sigma of 0.04
 K2-C51 \\sim K2-C63
 with sigma of 0.04
 K2-C52 \\sim K2-C64
 with sigma of 0.04
 K2-C53 \\sim K2-C65
 with sigma of 0.04
 K2-C54 \\sim K2-C66
 with sigma of 0.04
 K2-C55 \\sim K2-C67
 with sigma of 0.04
 O8-O9 \\sim O14-O15
 with sigma of 0.04
 O8-C46 \\sim O14-C58
 with sigma of 0.04
 O8-C47 \\sim O14-C59
 with sigma of 0.04
 O8-C52 \\sim O14-C64
 with sigma of 0.04
 O8-C53 \\sim O14-C65
 with sigma of 0.04
 O9-C45 \\sim O15-C57
 with sigma of 0.04
 O9-C46 \\sim O15-C58
 with sigma of 0.04
 O9-C49 \\sim O15-C61
 with sigma of 0.04
 O9-C53 \\sim O15-C65
 with sigma of 0.04
 O10-C45 \\sim O16-C57
 with sigma of 0.04
 O10-C49 \\sim O16-C61
 with sigma of 0.04
 O10-C50 \\sim O16-C62
 with sigma of 0.04
 O10-C51 \\sim O16-C63
 with sigma of 0.04
 O11-O13 \\sim O17-O19
 with sigma of 0.04
 O11-C44 \\sim O17-C56
 with sigma of 0.04
 O11-C47 \\sim O17-C59
 with sigma of 0.04
 O11-C52 \\sim O17-C64
 with sigma of 0.04
 O11-C54 \\sim O17-C66
 with sigma of 0.04
 O12-C48 \\sim O18-C60
 with sigma of 0.04
 O12-C50 \\sim O18-C62
 with sigma of 0.04
 O12-C51 \\sim O18-C63
 with sigma of 0.04
 O12-C55 \\sim O18-C67
 with sigma of 0.04
 O13-C44 \\sim O19-C56
 with sigma of 0.04
 O13-C48 \\sim O19-C60
 with sigma of 0.04
 O13-C54 \\sim O19-C66
 with sigma of 0.04
 O13-C55 \\sim O19-C67
 with sigma of 0.04
 C44-C54 \\sim C56-C66
 with sigma of 0.04
 C44-C55 \\sim C56-C67
 with sigma of 0.04
 C45-C49 \\sim C57-C61
 with sigma of 0.04
 C45-C53 \\sim C57-C65
 with sigma of 0.04
 C46-C52 \\sim C58-C64
 with sigma of 0.04
 C46-C53 \\sim C58-C65
 with sigma of 0.04
 C47-C52 \\sim C59-C64
 with sigma of 0.04
 C47-C54 \\sim C59-C66
 with sigma of 0.04
 C48-C51 \\sim C60-C63
 with sigma of 0.04
 C48-C55 \\sim C60-C67
 with sigma of 0.04
 C49-C50 \\sim C61-C62
 with sigma of 0.04
 C49-C51 \\sim C61-C63
 with sigma of 0.04
 C49-C53 \\sim C61-C65
 with sigma of 0.04
 C50-C51 \\sim C62-C63
 with sigma of 0.04
 C51-C55 \\sim C63-C67
 with sigma of 0.04
 C52-C53 \\sim C64-C65
 with sigma of 0.04
3. Others
 Sof(O14)=Sof(O15)=Sof(O16)=Sof(O17)=Sof(O18)=Sof(O19)=Sof(C56)=Sof(H56A)=
 Sof(H56B)=Sof(C57)=Sof(H57A)=Sof(H57B)=Sof(C58)=Sof(H58A)=Sof(H58B)=Sof(C59)=
 Sof(H59A)=Sof(H59B)=Sof(C60)=Sof(H60A)=Sof(H60B)=Sof(C61)=Sof(H61A)=Sof(H61B)=
 Sof(C62)=Sof(H62A)=Sof(H62B)=Sof(C63)=Sof(H63A)=Sof(H63B)=Sof(C64)=Sof(H64A)=
 Sof(H64B)=Sof(C65)=Sof(H65A)=Sof(H65B)=Sof(C66)=Sof(H66A)=Sof(H66B)=Sof(C67)=
 Sof(H67A)=Sof(H67B)=1-FVAR(1)
 Sof(O8)=Sof(O9)=Sof(O10)=Sof(O11)=Sof(O12)=Sof(O13)=Sof(C44)=Sof(H44A)=
 Sof(H44B)=Sof(C45)=Sof(H45A)=Sof(H45B)=Sof(C46)=Sof(H46A)=Sof(H46B)=Sof(C47)=
 Sof(H47A)=Sof(H47B)=Sof(C48)=Sof(H48A)=Sof(H48B)=Sof(C49)=Sof(H49A)=Sof(H49B)=
 Sof(C50)=Sof(H50A)=Sof(H50B)=Sof(C51)=Sof(H51A)=Sof(H51B)=Sof(C52)=Sof(H52A)=
 Sof(H52B)=Sof(C53)=Sof(H53A)=Sof(H53B)=Sof(C54)=Sof(H54A)=Sof(H54B)=Sof(C55)=
 Sof(H55A)=Sof(H55B)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C15(H15A,H15B), C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C9(H9A,
 H9B), C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B), C17(H17A,H17B), C18(H18A,
 H18B), C26(H26A,H26B), C44(H44A,H44B), C45(H45A,H45B), C46(H46A,H46B),
 C47(H47A,H47B), C48(H48A,H48B), C49(H49A,H49B), C50(H50A,H50B), C51(H51A,H51B),
  C52(H52A,H52B), C53(H53A,H53B), C54(H54A,H54B), C55(H55A,H55B), C56(H56A,
 H56B), C57(H57A,H57B), C58(H58A,H58B), C59(H59A,H59B), C60(H60A,H60B),
 C61(H61A,H61B), C62(H62A,H62B), C63(H63A,H63B), C64(H64A,H64B), C65(H65A,H65B),
  C66(H66A,H66B), C67(H67A,H67B)
4.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C20(H20), C23(H23), C29(H29), C30(H30), C31(H31), C34(H34),
 C38(H38), C39(H39), C40(H40)
4.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C11(H11A,H11B,H11C), C14(H14A,H14B,H14C), C19(H19A,H19B,
 H19C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C25(H25A,
 H25B,H25C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C32(H32A,H32B,H32C),
 C33(H33A,H33B,H33C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C37(H37A,H37B,
 H37C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C), C43(H43A,H43B,H43C)
;
_shelx_res_checksum              83783
_shelx_hkl_checksum              73997
_olex2_submission_special_instructions 'No special instructions were received'