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_4125545
_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_formula_moiety         'C96 H84 N12 O12, 4(C7 H8)'
_chemical_formula_sum            'C124 H116 N12 O12'
_chemical_formula_weight         1966.28
_chemical_name_systematic        'NDI Cage'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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                 100.010(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.3782(5)
_cell_length_b                   24.3080(7)
_cell_length_c                   29.6232(8)
_cell_measurement_reflns_used    9969
_cell_measurement_temperature    100
_cell_measurement_theta_max      55.94
_cell_measurement_theta_min      2.76
_cell_volume                     12323.2(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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      99.99
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'MX optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.2829
_diffrn_reflns_av_unetI/netI     0.1859
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            125354
_diffrn_reflns_point_group_measured_fraction_full 0.762
_diffrn_reflns_point_group_measured_fraction_max 0.762
_diffrn_reflns_theta_full        59.438
_diffrn_reflns_theta_max         59.44
_diffrn_reflns_theta_min         1.51
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.550
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_correction_T_min  0.5070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1187 before and 0.0714 after correction.
The Ratio of minimum to maximum transmission is 0.6746.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.060
_exptl_crystal_description       plate
_exptl_crystal_F_000             4160
_exptl_crystal_recrystallization_method
'grown through slow vapor diffusion of methanol into nitrobenzene solution over several days'
_exptl_crystal_size_max          0.157
_exptl_crystal_size_mid          0.143
_exptl_crystal_size_min          0.116
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2673
_refine_ls_number_reflns         27440
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.1539
_refine_ls_R_factor_gt           0.0887
_refine_ls_shift/su_max          0.095
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1084P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2000
_refine_ls_wR_factor_ref         0.2468
_reflns_Friedel_coverage         0.495
_reflns_Friedel_fraction_full    0.519
_reflns_Friedel_fraction_max     0.519
_reflns_number_gt                14764
_reflns_number_total             27440
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b00233_si_003.cif
_cod_data_source_block           ndi_cage
_cod_depositor_comments
'Adding full bibliography for 4125545--4125547.cif.'
_cod_database_code               4125545
_shelx_estimated_absorpt_t_max   0.939
_shelx_estimated_absorpt_t_min   0.919
_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
 C200-C201 = C202-C203 = C204-C205
 1.4 with sigma of 0.02
 C200-C205 \\sim C204-C203 \\sim C202-C201
 with sigma of 0.02
 C247-C246 \\sim C245-C244 \\sim C243-C242
 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C8(H8), C13(H13), C28(H28), C33(H33), C36(H36), C41(H41), C56(H56), C61(H61),
 C64(H64), C69(H69), C84(H84), C89(H89), C104(H104), C109(H109), C124(H124),
 C129(H129), C132(H132), C137(H137), C152(H152), C157(H157), C160(H160),
 C165(H165), C180(H180), C185(H185)
3.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C29(H29A,H29B),
 C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B), C37(H37A,H37B), C38(H38A,H38B),
  C39(H39A,H39B), C40(H40A,H40B), C57(H57A,H57B), C58(H58A,H58B), C59(H59A,
 H59B), C60(H60A,H60B), C65(H65A,H65B), C66(H66A,H66B), C67(H67A,H67B),
 C68(H68A,H68B), C85(H85A,H85B), C86(H86A,H86B), C87(H87A,H87B), C88(H88A,H88B),
  C105(H10C,H10D), C106(H10E,H10F), C107(H10G,H10H), C108(H10I,H10J), C125(H12C,
 H12D), C126(H12E,H12F), C127(H12G,H12H), C128(H12I,H12J), C133(H13A,H13B),
 C134(H13C,H13D), C135(H13E,H13F), C136(H13G,H13H), C153(H15A,H15B), C154(H15C,
 H15D), C155(H15E,H15F), C156(H15G,H15H), C161(H16A,H16B), C162(H16C,H16D),
 C163(H16E,H16F), C164(H16G,H16H), C181(H18A,H18B), C182(H18C,H18D), C183(H18E,
 H18F), C184(H18G,H18H)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C7(H7), C19(H19), C20(H20), C24(H24), C25(H25),
 C34(H34), C35(H35), C47(H47), C48(H48), C52(H52), C53(H53), C62(H62), C63(H63),
  C75(H75), C76(H76), C80(H80), C81(H81), C90(H90), C92(H92), C94(H94),
 C96(H96), C98(H98), C100(H100), C102(H102), C103(H103), C115(H115), C116(H116),
  C120(H120), C121(H121), C130(H130), C131(H131), C143(H143), C144(H144),
 C148(H148), C149(H149), C158(H158), C159(H159), C171(H171), C172(H172),
 C176(H176), C177(H177), C186(H186), C188(H188), C190(H190), C192(H192),
 C201(H201), C202(H202), C203(H203), C204(H204), C205(H205), C208(H208),
 C209(H209), C210(H210), C211(H211), C212(H212), C215(H215), C216(H216),
 C217(H217), C218(H218), C219(H219), C222(H222), C223(H223), C224(H224),
 C225(H225), C226(H226), C229(H229), C230(H230), C231(H231), C232(H232),
 C233(H233), C236(H236), C237(H237), C238(H238), C239(H239), C240(H240),
 C243(H243), C244(H244), C245(H245), C246(H246), C247(H247), C194(H194),
 C195(H195), C196(H196), C197(H197), C198(H198)
3.d Idealised Me refined as rotating group:
 C206(H20A,H20B,H20C), C213(H21A,H21B,H21C), C220(H22A,H22B,H22C), C227(H22D,
 H22E,H22F), C234(H23A,H23B,H23C), C241(H24A,H24B,H24C), C248(H24D,H24E,H24F),
 C199(H19A,H19B,H19C)
;
_shelx_res_checksum              48567
_shelx_hkl_checksum              29339
_shelx_fab_checksum              58252
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method
'crystal was mounted on loop, affixed with inert oil. '
_olex2_submission_special_instructions 'No special instructions were received'