Aminotroponiminates as tunable, redox-active ligands: reversible single electron transfer and reductive dimerisation.
Lichtenberg, C.; Krummenacher, I.; Chemical communications (Cambridge, England) 52 (2016) 10044–10047; doi:10.1039/c6cc05762d

data_7124944
_publ_section_title
;
 Aminotroponiminates as tunable, redox-active ligands: reversible single
 electron transfer and reductive dimerisation.
;
_journal_issue                   65
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              10044
_journal_page_last               10047
_journal_paper_doi               10.1039/c6cc05762d
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         '2(C28 H41 N2 Na2 O3)'
_chemical_formula_sum            'C56 H82 N4 Na4 O6'
_chemical_formula_weight         999.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-02-25
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-02-25 deposited with the CCDC.
2016-07-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.193(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.372(6)
_cell_length_b                   10.659(2)
_cell_length_c                   28.255(5)
_cell_measurement_reflns_used    2849
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.93
_cell_measurement_theta_min      2.25
_cell_volume                     5446(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.996
_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  0.0834
_diffrn_reflns_av_unetI/netI     0.1125
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            29900
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.085
_diffrn_reflns_theta_max         25.085
_diffrn_reflns_theta_min         1.126
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1104 before and 0.0500 after correction.
The Ratio of minimum to maximum transmission is 0.7814.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_description       block
_exptl_crystal_F_000             2152
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.679
_refine_diff_density_min         -0.624
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     628
_refine_ls_number_reflns         9649
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.1371
_refine_ls_R_factor_gt           0.0706
_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^)+(0.0521P)^2^+2.9135P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1264
_refine_ls_wR_factor_ref         0.1462
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5693
_reflns_number_total             9649
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc05762d3.cif
_cod_data_source_block           compound4
_cod_database_code               7124944
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.993
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H7-H8
 2.15 with sigma of 0.005
 H36-H35
 2.1 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Uanis(C51A) = Uanis(C51)
Uanis(C50) = Uanis(C50A)
Uanis(C29) = Uanis(C1)
Uanis(C3) = Uanis(C31)
Uanis(C47) = Uanis(C47A) = Uanis(C46)
4. Others
 Sof(H52C)=Sof(H52D)=Sof(H49C)=Sof(H49D)=Sof(C50A)=Sof(H50C)=Sof(H50D)=
 Sof(C51A)=Sof(H51C)=Sof(H51D)=1-FVAR(1)
 Sof(H52A)=Sof(H52B)=Sof(H49A)=Sof(H49B)=Sof(C50)=Sof(H50A)=Sof(H50B)=Sof(C51)=
 Sof(H51A)=Sof(H51B)=FVAR(1)
 Sof(H46C)=Sof(H46D)=Sof(H48C)=Sof(H48D)=Sof(C47)=Sof(H47C)=Sof(H47D)=1-FVAR(2)
 Sof(H46A)=Sof(H46B)=Sof(H48A)=Sof(H48B)=Sof(C47A)=Sof(H47A)=Sof(H47B)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C35(H35), C36(H36)
5.b Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C24(H24A,H24B), C27(H27A,H27B), C20(H20A,H20B), C21(H21A,
 H21B), C22(H22A,H22B), C25(H25A,H25B), C26(H26A,H26B), C17(H17A,H17B),
 C23(H23A,H23B), C18(H18A,H18B), C56(H56A,H56B), C53(H53A,H53B), C54(H54A,H54B),
  C55(H55A,H55B), C19(H19A,H19B), C45(H45A,H45B), C52(H52A,H52B), C52(H52C,
 H52D), C46(H46A,H46B), C46(H46C,H46D), C49(H49A,H49B), C49(H49C,H49D),
 C48(H48A,H48B), C48(H48C,H48D), C50(H50A,H50B), C47A(H47A,H47B), C51(H51A,
 H51B), C50A(H50C,H50D), C51A(H51C,H51D), C47(H47C,H47D)
5.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C3(H3), C12(H12), C16(H16), C15(H15), C13(H13), C4(H4),
 C14(H14), C31(H31), C34(H34), C33(H33), C32(H32), C40(H40), C41(H41), C43(H43),
  C42(H42), C44(H44)
5.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C38(H38A,H38B,H38C), C37(H37A,H37B,H37C)
;
_shelx_res_checksum              37911
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'