Supramolecular Tessellations by a Rigid Naphthalene Diimide Triangle.
Beldjoudi, Yassine; Narayanan, Ashwin; Roy, Indranil; Pearson, Tyler J.; Cetin, M. Mustafa; Nguyen, Minh T.; Krzyaniak, Matthew D.; Alsubaie, Fehaid M.; Wasielewski, Michael R.; Stupp, Samuel I.; Stoddart, J. Fraser; Journal of the American Chemical Society  (2019) –; doi:10.1021/jacs.9b08758

data_4127313
_publ_section_title
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 Supramolecular Tessellations by a Rigid Naphthalene Diimide Triangle.
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_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b08758
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C60 H42 N6 O12, 0.5(C4 H10 O), 4(C2 H3 N)'
_chemical_formula_sum            'C70 H59 N10 O12.5'
_chemical_formula_weight         1240.27
_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     dual
_audit_creation_date             2019-07-19
_audit_creation_method
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
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_audit_update_record
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2019-07-19 # Formatted by publCIF

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_cell_angle_alpha                90
_cell_angle_beta                 90.488(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.9512(11)
_cell_length_b                   15.0324(11)
_cell_length_c                   25.0891(17)
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.52
_cell_measurement_theta_min      2.46
_cell_volume                     6015.8(7)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      100.02
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            73298
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.586
_diffrn_reflns_theta_min         1.507
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0623 before and 0.0467 after correction.
The Ratio of minimum to maximum transmission is 0.9095.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description       block
_exptl_crystal_F_000             2596
_exptl_crystal_size_max          0.171
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.115
_refine_diff_density_max         1.363
_refine_diff_density_min         -1.334
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.5(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1707
_refine_ls_number_reflns         34154
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0574
_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^)+(0.0783P)^2^+1.8348P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1387
_refine_ls_wR_factor_ref         0.1480
_reflns_Friedel_coverage         0.869
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.890
_reflns_number_gt                28348
_reflns_number_total             34154
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b08758_si_002.cif
_cod_data_source_block           yb063nua2
_cod_original_formula_sum        'C70 H59 N10 O12.50'
_cod_database_code               4127313
_publcif_datablock.id            {40778cff-0668-400b-82ca-836b2e2a4490}
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.984
_olex2_refinement_description
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1. Twinned data refinement
 Scales: 1.5(7)
 -0.5(7)
2. 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 C(H,H,H,H,H,H) groups
3. Restrained distances
 C137-C3AA
 1.54 with sigma of 0.02
 C137-C054
 1.54 with sigma of 0.02
 C138-C1AA
 1.54 with sigma of 0.01
 C138-C04X
 1.54 with sigma of 0.01
 C137-C0AA
 1.54 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C138) \\sim Ueq, Uanis(C1AA) \\sim Ueq: with sigma of 0.025 and sigma for
terminal atoms of 0.2
Uanis(C1AA) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.01
Uanis(C3AA) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.01
Uanis(C138) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C137) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C0AA) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(O25) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.05
Uanis(C137) = Uanis(C138)
Uanis(C04X) = Uanis(C1AA)
Uanis(C054) = Uanis(C3AA)
5. Others
 Fixed Sof: H13A(0.5) H13B(0.5) H13C(0.5) H13D(0.5) C1AA(0.5) H1AA(0.5)
 H1AC(0.5) H1AB(0.5) C3AA(0.33333) H3AA(0.33333) H3AB(0.33333) H3AC(0.33333)
 C04X(0.5) H04A(0.5) H04B(0.5) H04C(0.5) H13E(0.5) H13F(0.5) H13G(0.5)
 H13H(0.5) C054(0.33333) H05A(0.33333) H05B(0.33333) H05C(0.33333) C1A(0.5)
 N16A(0.5) N16B(0.5) H12F(0.5) H12G(0.5) H12H(0.5) H12C(0.5) H12D(0.5)
 H12E(0.5) C128(0.5) C0AA(0.33333) H0AA(0.33333) H0AB(0.33333) H0AC(0.33333)
 Fixed Uiso: H3AA(0.14718) H3AB(0.14718) H3AC(0.14718)
6.a Ternary CH refined with riding coordinates:
 C43(H43), C48(H48), C49(H49), C50(H50), C55(H55), C56(H56), C103(H103),
 C104(H104), C109(H109), C110(H110), C115(H115), C116(H116)
6.b Secondary CH2 refined with riding coordinates:
 C44(H44A,H44B), C45(H45A,H45B), C46(H46A,H46B), C47(H47A,H47B), C51(H51A,
 H51B), C52(H52A,H52B), C53(H53A,H53B), C54(H54A,H54B), C57(H57A,H57B),
 C58(H58A,H58B), C59(H59A,H59B), C60(H60A,H60B), C105(H10A,H10B), C106(H10C,
 H10D), C107(H10E,H10F), C108(H10G,H10H), C111(H11A,H11B), C112(H11C,H11D),
 C113(H11E,H11F), C114(H11G,H11H), C117(H11I,H11J), C118(H11K,H11L), C119(H11M,
 H11N), C120(H12A,H12B), C138(H13A,H13B), C138(H13C,H13D), C137(H13E,H13F),
 C137(H13G,H13H)
6.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C11(H11), C12(H12), C18(H18), C19(H19), C24(H24), C25(H25),
 C34(H34), C35(H35), C38(H38), C39(H39), C66(H66), C67(H67), C71(H71), C72(H72),
  C80(H80), C81(H81), C85(H85), C86(H86), C94(H94), C95(H95), C99(H99),
 C100(H100)
6.d Idealised Me refined as rotating group:
 C1AA(H1AA,H1AC,H1AB), C3AA(H3AA,H3AB,H3AC), C04X(H04A,H04B,H04C), C054(H05A,
 H05B,H05C), C127(H12F,H12G,H12H), C127(H12C,H12D,H12E), C136(H13I,H13J,H13K),
 C126(H12I,H12J,H12K), C134(H13L,H13M,H13N), C130(H13O,H13P,H13Q), C132(H13R,
 H13S,H13T), C122(H12L,H12M,H12N), C124(H12O,H12P,H12Q), C0AA(H0AA,H0AB,H0AC)
;
_shelx_res_checksum              39781
_shelx_hkl_checksum              56492
_olex2_submission_special_instructions 'No special instructions were received'
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
_publcif_funding_html
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