Electron Hopping and Charge Separation within a Naphthalene-1,4:5,8-bis(dicarboximide) Chiral Covalent Organic Cage.
Šolomek, Tomáš; Powers-Riggs, Natalia E; Wu, Yi-Lin; Young, Ryan M.; Krzyaniak, Matthew D.; Horwitz, Noah E.; Wasielewski, Michael R.; Journal of the American Chemical Society 139 (2017) 3348–3351; doi:10.1021/jacs.7b00233

data_4125546
_publ_section_title
;
 Electron Hopping and Charge Separation within a
 Naphthalene-1,4:5,8-bis(dicarboximide) Chiral Covalent Organic Cage.
;
_journal_issue                   9
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3348
_journal_page_last               3351
_journal_paper_doi               10.1021/jacs.7b00233
_journal_volume                  139
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety
'C96 H84 N12 O12, 2(C6 H5 N O2), C12 H8 N2 O4'
_chemical_formula_sum            'C120 H102 N16 O20'
_chemical_formula_weight         2088.17
_chemical_name_systematic        'NDI Cage Nitrobenzene'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_symmetry_space_group_name_Hall  'C 2c 2'
_symmetry_space_group_name_H-M   'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-02-08
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.0811(5)
_cell_length_b                   33.4347(10)
_cell_length_c                   21.6852(6)
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    100
_cell_measurement_theta_max      65.14
_cell_measurement_theta_min      3.70
_cell_volume                     12384.4(6)
_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    'XM (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0370
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            51187
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        65.138
_diffrn_reflns_theta_max         65.14
_diffrn_reflns_theta_min         2.04
_diffrn_source                   microsource
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6426
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0949 before and 0.0595 after correction.
The Ratio of minimum to maximum transmission is 0.8538.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.120
_exptl_crystal_description       Tabular
_exptl_crystal_F_000             4376
_exptl_crystal_recrystallization_method
'grown through slow vapor diffusion of methanol into nitrobenzene solution over several days'
_exptl_crystal_size_max          0.258
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 4515 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.87(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     719
_refine_ls_number_reflns         10519
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0575
_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^)+(0.0976P)^2^+13.6818P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1690
_refine_ls_wR_factor_ref         0.1727
_reflns_Friedel_coverage         0.842
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                10223
_reflns_number_total             10519
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b00233_si_002.cif
_cod_data_source_block           cagenitrobenzene
_cod_depositor_comments
'Adding full bibliography for 4125545--4125547.cif.'
_cod_original_cell_volume        12384.5(6)
_cod_database_code               4125546
_shelx_estimated_absorpt_t_max   0.933
_shelx_estimated_absorpt_t_min   0.853
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(O11)=Sof(N9)=Sof(O12)=1-FVAR(1)
 Sof(O9)=Sof(N8)=Sof(O10)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C8(H8), C33(H33), C36(H36), C28(H28), C13(H13), C41(H41)
3.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C29(H29A,H29B), C32(H32A,H32B), C9(H9A,H9B), C11(H11A,H11B),
 C30(H30A,H30B), C10(H10A,H10B), C31(H31A,H31B), C37(H37A,H37B), C39(H39A,H39B),
  C40(H40A,H40B), C38(H38A,H38B)
3.c Aromatic/amide H refined with riding coordinates:
 C34(H34), C6(H6), C7(H7), C35(H35), C4(H4), C2(H2), C25(H25), C24(H24),
 C46(H46), C45(H45), C19(H19), C60(H60), C58(H58), C20(H20), C57(H57), C56(H56),
  C51(H51), C52(H52), C53(H53), C54(H54), C50(H50)
3.d Fitted hexagon refined as free rotating group:
 C51(C52,C53,C54,C49,C50)
;
_shelx_res_checksum              43835
_shelx_hkl_checksum              58814
_shelx_fab_checksum              71845
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_completion    2016-11-22
_olex2_date_sample_data_collection 2016-11-21
_olex2_date_sample_submission    2016-11-21
_olex2_exptl_crystal_mounting_method
'affixed with inert oil and mounted on a loop'
_olex2_submission_special_instructions 'No special instructions were received'