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

data_1567939
_publ_section_title
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 Taming the Stilbene Radical Anion
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_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC04451J
_journal_year                    2022
_chemical_formula_moiety
'C36 H108 Fe2 N6 Si12, C24 H48 K2 O12, C14 H12, 0.5(C24 H48 O12), 0.5(C24 H46 K2 O12)'
_chemical_formula_sum            'C98 H213 Fe2 K3 N6 O24 Si12'
_chemical_formula_weight         2425.81
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-06-13
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
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2022-06-13 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.037(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   16.0976(10)
_cell_length_b                   15.8981(8)
_cell_length_c                   26.7651(15)
_cell_measurement_reflns_used    9874
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      29.98
_cell_measurement_theta_min      2.32
_cell_volume                     6840.1(7)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'Bruker BIS V6.2.14/2020-04-30'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (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 0.997
_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  0.0474
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            182148
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.065
_diffrn_reflns_theta_min         1.930
_exptl_absorpt_coefficient_mu    0.468
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1501 before and 0.0584 after correction. The Ratio of minimum to maximum transmission is 0.8865. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'dark brown'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_description       plate
_exptl_crystal_F_000             2624
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.668
_refine_diff_density_min         -0.849
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     889
_refine_ls_number_reflns         20029
_refine_ls_number_restraints     149
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0441
_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^)+(0.0498P)^2^+5.5297P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1176
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15332
_reflns_number_total             20029
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc04451j2.cif
_cod_data_source_block           1
_cod_database_code               1567939
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.955
_shelx_estimated_absorpt_t_min   0.872
_olex2_refinement_description
;
1. Restrained distances
 O3-C2 \\sim O3-C1 \\sim O4-C29 \\sim O4-C5 \\sim O5-C6 \\sim O5-C7 \\sim
O6-C15 \\sim O6-C16
 with sigma of 0.02
 C1-C29 \\sim C5-C6 \\sim C7-C15 \\sim C16-O1
 with sigma of 0.02
 C2-C1 \\sim C29-C5 \\sim C6-C7 \\sim C15-C16
 with sigma of 0.04
 O3-C29 \\sim O4-C6 \\sim O5-C15 \\sim O6-O1 \\sim O4-C1 \\sim O5-C5 \\sim O6-C7
 with sigma of 0.04
2. Uiso/Uaniso restraints and constraints
O3 \\sim O4 \\sim O5 \\sim O6 \\sim C2 \\sim C1 \\sim C29 \\sim C5 \\sim C6
\\sim C7 \\sim C15 \\sim C16 \\sim O1 \\sim O2: within 2A with sigma of 0.04
and sigma for terminal atoms of 0.08 within 2A
C22 \\sim C31: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 2A
C1: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(C22) \\sim Ueq, Uanis(C31) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(C31) \\sim Ueq, Uanis(C22) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
Uanis(C22) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Rigid body (RIGU) restrains
 O3, O4, O5, O6, C2, C1, C29, C5, C6, C7, C15, C16, O1, O2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C22, C31
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: C00U(0.5) H00U(0.5) C00X(0.5) H00X(0.5) C00Y(0.5) H00Y(0.5)
 C00Z(0.5) C011(0.5) H011(0.5) C018(0.5) H018(0.5) C01V(0.5) H01V(0.5) C8(0.5)
 H8(0.5) C14(0.5) H14(0.5) C9(0.5) C10(0.5) H10(0.5) C11(0.5) H11(0.5) C12(0.5)
 H12(0.5) C13(0.5) H13(0.5) O3(0.5) O4(0.5) O5(0.5) O6(0.5) C2(0.5) H2A(0.5)
 H2B(0.5) C1(0.5) H1A(0.5) H1B(0.5) C29(0.5) H29A(0.5) H29B(0.5) C5(0.5)
 H5A(0.5) H5B(0.5) C6(0.5) H6A(0.5) H6B(0.5) C7(0.5) H7A(0.5) H7B(0.5) C15(0.5)
 H15A(0.5) H15B(0.5) C16(0.5) H16A(0.5) H16B(0.5) O1(0.5) O2(0.5) C17(0.5)
 H17A(0.5) H17B(0.5) C18(0.5) H18A(0.5) H18B(0.5) C3(0.5) H3A(0.5) H3B(0.5)
 C4(0.5) H4A(0.5) H4B(0.5) K1(0.5) O7(0.5) O8(0.5) O9(0.5) C21(0.5) H21A(0.5)
 H21B(0.5) O10(0.5) C19(0.5) H19A(0.5) H19B(0.5) C20(0.5) H20A(0.5) H20B(0.5)
 O18(0.5) C24(0.5) H24A(0.5) H24B(0.5) C25(0.5) H25A(0.5) H25B(0.5) C26(0.5)
 H26A(0.5) H26B(0.5) C27(0.5) H27(0.5) C28(0.5) H28A(0.5) H28B(0.5) C22(0.5)
 H22A(0.5) H22B(0.5) C23(0.5) H23A(0.5) H23B(0.5) C30(0.5) H30A(0.5) H30B(0.5)
 C31(0.5) H31A(0.5) H31B(0.5) O17(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C57(H57A,H57B), C58(H58A,H58B), C59(H59A,H59B), C60(H60A,H60B), C61(H61A,
 H61B), C62(H62A,H62B), C66(H66A,H66B), C67(H67A,H67B), C73(H73A,H73B),
 C74(H74A,H74B), C78(H78A,H78B), C80(H80A,H80B), C2(H2A,H2B), C1(H1A,H1B),
 C29(H29A,H29B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C15(H15A,H15B),
 C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C3(H3A,H3B), C4(H4A,H4B),
 C21(H21A,H21B), C19(H19A,H19B), C20(H20A,H20B), C24(H24A,H24B), C25(H25A,H25B),
  C26(H26A,H26B), C28(H28A,H28B), C22(H22A,H22B), C23(H23A,H23B), C30(H30A,
 H30B), C31(H31A,H31B)
5.b Aromatic/amide H refined with riding coordinates:
 C00U(H00U), C00X(H00X), C00Y(H00Y), C011(H011), C018(H018), C01V(H01V),
 C8(H8), C14(H14), C10(H10), C11(H11), C12(H12), C13(H13), C27(H27)
5.c Fitted hexagon refined as free rotating group:
 C14(C9,C10,C11,C12,C13)
5.d Idealised Me refined as rotating group:
 C51(H51A,H51B,H51C), C52(H52A,H52B,H52C), C53(H53A,H53B,H53C), C54(H54A,H54B,
 H54C), C55(H55A,H55B,H55C), C56(H56A,H56B,H56C), C63(H63A,H63B,H63C), C64(H64A,
 H64B,H64C), C65(H65A,H65B,H65C), C68(H68A,H68B,H68C), C69(H69A,H69B,H69C),
 C70(H70A,H70B,H70C), C71(H71A,H71B,H71C), C72(H72A,H72B,H72C), C75(H75A,H75B,
 H75C), C76(H76A,H76B,H76C), C77(H77A,H77B,H77C), C79(H79A,H79B,H79C)
;
_shelx_res_checksum              51861
_shelx_hkl_checksum              24323
_olex2_submission_special_instructions 'No special instructions were received'