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_4126115
_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_formula_moiety         'C22 H24 N2 O4'
_chemical_formula_sum            'C22 H24 N2 O4'
_chemical_formula_weight         380.43
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-09-16
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2016-09-21 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 112.440(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.492(3)
_cell_length_b                   5.2268(7)
_cell_length_c                   27.504(5)
_cell_measurement_reflns_used    2070
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      56.734
_cell_measurement_theta_min      3.477
_cell_volume                     3652.9(9)
_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, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.796
_diffrn_measured_fraction_theta_max 0.993
_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  0.1217
_diffrn_reflns_av_unetI/netI     0.1258
_diffrn_reflns_Laue_measured_fraction_full 0.796
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            14240
_diffrn_reflns_point_group_measured_fraction_full 0.796
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         59.282
_diffrn_reflns_theta_min         1.738
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.779
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_correction_T_min  0.6055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1031 before and 0.0671 after correction.
The Ratio of minimum to maximum transmission is 0.8056.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_description       needle
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.542
_exptl_crystal_size_mid          0.026
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.218
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.175
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.277
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     506
_refine_ls_number_reflns         5220
_refine_ls_number_restraints     864
_refine_ls_restrained_S_all      1.191
_refine_ls_R_factor_all          0.1826
_refine_ls_R_factor_gt           0.1487
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3346
_refine_ls_wR_factor_ref         0.3623
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3695
_reflns_number_total             5220
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b01209_si_002.cif
_cod_data_source_block           cx0842
_cod_database_code               4126115
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.678
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.597(4) 0.403(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5.a Ternary CH refined with riding coordinates:
 C11(H11), C17(H17), C11A(H11A), C17A(H17A)
5.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,
 H16B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B),
 C22(H22A,H22B), C12A(H12C,H12D), C13A(H13C,H13D), C14A(H14C,H14D), C15A(H15C,
 H15D), C16A(H16C,H16D), C18A(H18C,H18D), C19A(H19C,H19D), C20A(H20C,H20D),
 C21A(H21C,H21D), C22A(H22C,H22D)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C3A(H3A), C8A(H8A)
;
_olex2_date_sample_data_collection 2016-09-12
_olex2_date_sample_submission    2016-09-09
_olex2_diffrn_ambient_temperature_device edit
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id cx0842
_olex2_submission_special_instructions 'No special instructions were received'