Redox-Active Macrocycles for Organic Rechargeable Batteries.
Kim, Dong Jun; Hermann, Keith R.; Prokofjevs, Aleksandrs; Otley, Michael T.; Pezzato, Cristian; Owczarek, Magdalena; Stoddart, J. Fraser; Journal of the American Chemical Society 139 (2017) 6635–6643; doi:10.1021/jacs.7b01209

data_4126023
_publ_section_title
;
 Redox-Active Macrocycles for Organic Rechargeable Batteries.
;
_journal_issue                   19
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6635
_journal_page_last               6643
_journal_paper_doi               10.1021/jacs.7b01209
_journal_volume                  139
_journal_year                    2017
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C48 H36 N6 O12, 1.5(C5 H9 N O)'
_chemical_formula_sum            'C55.5 H49.5 N7.5 O13.5'
_chemical_formula_weight         1037.52
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-08-06
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                83.6115(16)
_cell_angle_beta                 79.6903(15)
_cell_angle_gamma                70.5894(15)
_cell_formula_units_Z            2
_cell_length_a                   10.9086(2)
_cell_length_b                   15.7319(3)
_cell_length_c                   17.5116(4)
_cell_measurement_reflns_used    6232
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      54.184
_cell_measurement_theta_min      2.568
_cell_volume                     2784.30(10)
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 V2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.667
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Quazar optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_unetI/netI     0.0709
_diffrn_reflns_Laue_measured_fraction_full 0.667
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19595
_diffrn_reflns_point_group_measured_fraction_full 0.617
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         54.217
_diffrn_reflns_theta_min         2.569
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.749
_exptl_absorpt_correction_T_max  0.7507
_exptl_absorpt_correction_T_min  0.6235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0562 before and 0.0447 after correction.
The Ratio of minimum to maximum transmission is 0.8306.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_description       plate
_exptl_crystal_F_000             1086
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.042
_exptl_crystal_size_min          0.018
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 3633 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.4(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1446
_refine_ls_number_reflns         12433
_refine_ls_number_restraints     1425
_refine_ls_restrained_S_all      0.937
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0593
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1051P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1475
_refine_ls_wR_factor_ref         0.1601
_reflns_Friedel_coverage         0.852
_reflns_Friedel_fraction_full    0.568
_reflns_Friedel_fraction_max     0.840
_reflns_number_gt                9523
_reflns_number_total             12433
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b01209_si_004.cif
_cod_data_source_block           cx0536
_cod_depositor_comments          'Adding full bibliography for 4126023.cif.'
_cod_original_formula_sum        'C55.50 H49.50 N7.50 O13.50'
_cod_database_code               4126023
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.881
_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
 N3S-C15S \\sim N4S-C20S \\sim N2S_$1-C10S_$1 \\sim N1S-C5S
 with sigma of 0.01
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(O4S)=Sof(N4S)=Sof(C16S)=Sof(C17S)=Sof(H17A)=Sof(H17B)=Sof(C18S)=Sof(H18C)=
 Sof(H18D)=Sof(C19S)=Sof(H19C)=Sof(H19D)=Sof(C20S)=Sof(H20C)=Sof(H20D)=
 Sof(H20E)=1-FVAR(1)
 Sof(O3S)=Sof(N3S)=Sof(C11S)=Sof(C12S)=Sof(H12A)=Sof(H12B)=Sof(C13S)=Sof(H13A)=
 Sof(H13B)=Sof(C14S)=Sof(H14A)=Sof(H14B)=Sof(C15S)=Sof(H15A)=Sof(H15B)=
 Sof(H15C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C1(H1), C6(H6), C17(H17), C22(H22), C33(H33), C38(H38), C49(H49), C54(H54),
 C65(H65), C70(H70), C81(H81), C86(H86)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C18(H18A,H18B), C19(H19A,
 H19B), C20(H20A,H20B), C21(H21A,H21B), C34(H34A,H34B), C35(H35A,H35B),
 C36(H36A,H36B), C37(H37A,H37B), C50(H50A,H50B), C51(H51A,H51B), C52(H52A,H52B),
  C53(H53A,H53B), C66(H66A,H66B), C67(H67A,H67B), C68(H68A,H68B), C69(H69A,
 H69B), C82(H82A,H82B), C83(H83A,H83B), C84(H84A,H84B), C85(H85A,H85B),
 C1S(H1SA,H1SB), C2S(H2SA,H2SB), C3S(H3SA,H3SB), C6S(H6SA,H6SB), C7S(H7SA,H7SB),
  C8S(H8SA,H8SB), C12S(H12A,H12B), C13S(H13A,H13B), C14S(H14A,H14B), C17S(H17A,
 H17B), C18S(H18C,H18D), C19S(H19C,H19D)
5.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C14(H14), C25(H25), C30(H30), C41(H41), C46(H46), C57(H57), C62(H62),
 C73(H73), C78(H78), C89(H89), C94(H94)
5.d Idealised Me refined as rotating group:
 C5S(H5SA,H5SB,H5SC), C10S(H10A,H10B,H10C), C15S(H15A,H15B,H15C), C20S(H20C,
 H20D,H20E)
;
_smtbx_masks_special_details
;
The solvent masking procedure as implemented in Olex2 was used to remove the
electronic contribution of solvent molecules from the refinement.  As the exact
solvent content is not known, only the atoms used in the refinement model are
reported in the formula here.

Total solvent accessible volume / cell = 434.5 Ang^3^ [15.6%]
Total electron count / cell = 101.2
;
_shelx_res_checksum              80724
_shelx_hkl_checksum              970
_olex2_date_sample_data_collection 2015-07-30
_olex2_date_sample_submission    2015-07-29
_olex2_submission_original_sample_id cx0536
_olex2_submission_special_instructions 'No special instructions were received'