Stabilizing the Naphthalenediimide Radical within a Tetracationic Cyclophane.
Jiao, Tianyu; Cai, Kang; Nelson, Jordan N.; Jiao, Yang; Qiu, Yunyan; Wu, Guangcheng; Zhou, Jiawang; Cheng, Chuyang; Shen, Dengke; Feng, Yuanning; Liu, Zhichang; Wasielewski, Michael R.; Stoddart, J. Fraser; Li, Hao; Journal of the American Chemical Society 141 (2019) 16915–16922; doi:10.1021/jacs.9b08926

data_4127942
_publ_section_title
;
 Stabilizing the Naphthalenediimide Radical within a Tetracationic
 Cyclophane.
;
_journal_issue                   42
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16915
_journal_page_last               16922
_journal_paper_doi               10.1021/jacs.9b08926
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety
'4(F6 P), C17 H21 N2 O6, 2(C24 H20 N2), 3(C2 H3 N)'
_chemical_formula_sum            'C71 H70 F24 N9 O6 P4'
_chemical_formula_weight         1725.24
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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             2017-09-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                112.760(5)
_cell_angle_beta                 91.764(4)
_cell_angle_gamma                102.586(5)
_cell_formula_units_Z            2
_cell_length_a                   11.3842(6)
_cell_length_b                   18.1455(10)
_cell_length_c                   20.4946(11)
_cell_measurement_reflns_used    5373
_cell_measurement_temperature    181.8
_cell_measurement_theta_max      29.2882
_cell_measurement_theta_min      3.0220
_cell_volume                     3778.9(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      181.8
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega  -68.00    2.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  127.0000 -122.0000 70

  2 omega  -64.00   38.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808  -38.0000   30.0000 102

  3 omega  -51.00  -20.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808  143.0000   47.0000 31

  4 omega  -15.00   73.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   38.0000 -150.0000 88
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0101768000
_diffrn_orient_matrix_UB_12      -0.0216410000
_diffrn_orient_matrix_UB_13      -0.0355920000
_diffrn_orient_matrix_UB_21      -0.0453525000
_diffrn_orient_matrix_UB_22      0.0142808000
_diffrn_orient_matrix_UB_23      -0.0126591000
_diffrn_orient_matrix_UB_31      0.0445291000
_diffrn_orient_matrix_UB_32      0.0352675000
_diffrn_orient_matrix_UB_33      0.0022361000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0793
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            24484
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         3.028
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_description       block
_exptl_crystal_F_000             1766
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.28
_refine_diff_density_max         1.574
_refine_diff_density_min         -0.748
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.284
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1042
_refine_ls_number_reflns         13784
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.284
_refine_ls_R_factor_all          0.1701
_refine_ls_R_factor_gt           0.1216
_refine_ls_shift/su_max          0.001
_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          0.3338
_refine_ls_wR_factor_ref         0.3884
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8269
_reflns_number_total             13784
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b08926_si_004.cif
_cod_data_source_block           170907_ty_ex_ndi
_cod_original_cell_volume        3778.8(4)
_cod_database_code               4127942
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c h n o p f'
_shelx_estimated_absorpt_t_max   0.942
_shelx_estimated_absorpt_t_min   0.903
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O5) = Uanis(O5A)
Uanis(C62) = Uanis(C62A)
3. Others
 Sof(H61C)=Sof(H61D)=Sof(H63C)=Sof(H63D)=Sof(O5A)=Sof(C62A)=Sof(H62C)=
 Sof(H62D)=1-FVAR(1)
 Sof(O5)=Sof(H61A)=Sof(H61B)=Sof(C62)=Sof(H62A)=Sof(H62B)=Sof(H63A)=Sof(H63B)=
 FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C56(H56A,H56B), C58(H58A,H58B), C59(H59A,H59B), C60(H60A,H60B), C61(H61A,
 H61B), C61(H61C,H61D), C62(H62A,H62B), C63(H63A,H63B), C63(H63C,H63D),
 C17(H17A,H17B), C24(H24A,H24B), C41(H41A,H41B), C48(H48A,H48B), C62A(H62C,H62D)
4.b Aromatic/amide H refined with riding coordinates:
 C51(H51), C52(H52), C57(H57), C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C8(H8),
 C10(H10), C11(H11), C13(H13), C14(H14), C15(H15), C16(H16), C19(H19), C20(H20),
  C22(H22), C23(H23), C25(H25), C26(H26), C28(H28), C29(H29), C31(H31),
 C32(H32), C34(H34), C35(H35), C37(H37), C38(H38), C39(H39), C40(H40), C43(H43),
  C44(H44), C46(H46), C47(H47)
4.c Idealised Me refined as rotating group:
 C65(H65A,H65B,H65C), C67(H67A,H67B,H67C), C69(H69A,H69B,H69C), C71(H71A,H71B,
 H71C)
4.d Idealised tetrahedral OH refined as rotating group:
 O6(H6)
;
_shelx_res_checksum              7332
_shelx_hkl_checksum              40560
_olex2_submission_special_instructions 'No special instructions were received'