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_4126114
_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 ad
_chemical_formula_moiety         'C32 H24 N4 O8'
_chemical_formula_sum            'C32 H24 N4 O8'
_chemical_formula_weight         592.55
_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
_audit_creation_date             2016-08-14
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-08-28 # Formatted by publCIF
;
_cell_angle_alpha                97.113(2)
_cell_angle_beta                 100.141(2)
_cell_angle_gamma                104.254(2)
_cell_formula_units_Z            1
_cell_length_a                   6.9466(5)
_cell_length_b                   7.5493(5)
_cell_length_c                   13.1221(9)
_cell_measurement_reflns_used    9007
_cell_measurement_temperature    200
_cell_measurement_theta_max      68.110
_cell_measurement_theta_min      3.475
_cell_volume                     646.39(8)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'MX optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0115
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            34689
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.110
_diffrn_reflns_theta_min         3.475
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.931
_exptl_absorpt_correction_T_max  0.7379
_exptl_absorpt_correction_T_min  0.6489
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0927 before and 0.0340 after correction.
The Ratio of minimum to maximum transmission is 0.8794.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_description       Plate
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.283
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.087
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.03(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         4452
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0242
_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^)+(0.0458P)^2^+0.0902P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0674
_refine_ls_wR_factor_ref         0.0676
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                4424
_reflns_number_total             4452
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b01209_si_003.cif
_cod_data_source_block           cx0825_0m
_cod_database_code               4126114
_shelx_estimated_absorpt_t_max   0.923
_shelx_estimated_absorpt_t_min   0.779
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.97(15) 0.03(15)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5), C18(H18), C19(H19)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1a,H1b), C2(H2a,H2b), C3(H3a,H3b), C6(H6a,H6b), C20(H20a,H20b), C21(H21a,
 H21b), C22(H22a,H22b), C23(H23a,H23b)
3.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C15(H15), C26(H26), C31(H31)
;
_shelx_res_checksum              51883
_shelx_hkl_checksum              6384
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-08-08
_olex2_date_sample_submission    2016-08-08
_olex2_submission_original_sample_id cx0825
_olex2_submission_special_instructions 'No special instructions were received'