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_4127315
_publ_section_title
;
 Supramolecular Tessellations by a Rigid Naphthalene Diimide Triangle.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b08758
_journal_year                    2019
_chemical_formula_moiety
'C60 H42 N6 O12, C4 H3 S2.5, C6 H4 S4, 0.5(C4 H2 S3), C3 H3 S2'
_chemical_formula_sum            'C75 H53 N6 O12 S10'
_chemical_formula_weight         1550.83
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-07-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-26 # Formatted by publCIF

;
_cell_angle_alpha                69.423(4)
_cell_angle_beta                 69.340(4)
_cell_angle_gamma                70.959(4)
_cell_formula_units_Z            2
_cell_length_a                   15.8923(10)
_cell_length_b                   15.9624(10)
_cell_length_c                   16.7921(11)
_cell_measurement_reflns_used    7605
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      67.239
_cell_measurement_theta_min      2.917
_cell_volume                     3630.8(4)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX2 V2014.11-0 (Bruker, 2014)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      103.26
_diffrn_measured_fraction_theta_full 0.895
_diffrn_measured_fraction_theta_max 0.895
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0651
_diffrn_reflns_Laue_measured_fraction_full 0.895
_diffrn_reflns_Laue_measured_fraction_max 0.895
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15466
_diffrn_reflns_point_group_measured_fraction_full 0.895
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        65.114
_diffrn_reflns_theta_max         65.114
_diffrn_reflns_theta_min         2.918
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.369
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1066 before and 0.0665 after correction. The Ratio of minimum to maximum transmission is 0.6159. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_description       plate
_exptl_crystal_F_000             1602
_exptl_crystal_size_max          0.115
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.072
_refine_diff_density_max         1.169
_refine_diff_density_min         -0.947
_refine_diff_density_rms         0.206
_refine_ls_extinction_coef       0.0249(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1111
_refine_ls_number_reflns         11083
_refine_ls_number_restraints     350
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.2059
_refine_ls_R_factor_gt           0.1995
_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^)+(0.1937P)^2^+80.1773P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4607
_refine_ls_wR_factor_ref         0.4653
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10161
_reflns_number_total             11083
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b08758_si_005.cif
_cod_data_source_block           yb016bisf
_cod_database_code               4127315
_publcif_datablock.id            {05449f5a-9d32-4da0-9efc-d9b7ea75cebd}
_shelx_shelxl_version_number     2018/3
_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
2. Restrained distances
 S10-C72
 1.7 with sigma of 0.02
 S8A-C69A
 1.71 with sigma of 0.02
 C68A-S8A
 1.73 with sigma of 0.02
 C35-C40
 1.54 with sigma of 0.02
 C20-C15
 1.54 with sigma of 0.02
 C58-C53
 1.54 with sigma of 0.02
 C69A-C70A
 1.33 with sigma of 0.02
 C71_$1-C72_$1
 1.28 with sigma of 0.02
 C39-C38
 1.54 with sigma of 0.01
 C40-C39
 1.54 with sigma of 0.01
 C40-C35
 1.54 with sigma of 0.01
 C35-C36
 1.54 with sigma of 0.01
 C36-C37
 1.54 with sigma of 0.01
 C37-C38
 1.54 with sigma of 0.01
 C15-C20
 1.54 with sigma of 0.01
 C20-C19
 1.54 with sigma of 0.01
 C19-C18
 1.54 with sigma of 0.01
 C18-C17
 1.54 with sigma of 0.01
 C17-C16
 1.54 with sigma of 0.01
 C16-C15
 1.54 with sigma of 0.01
 C53-C58
 1.54 with sigma of 0.01
 C58-C57
 1.54 with sigma of 0.01
 C57-C56
 1.54 with sigma of 0.01
 C56-C55
 1.54 with sigma of 0.01
 C55-C54
 1.54 with sigma of 0.01
 C54-C53
 1.54 with sigma of 0.01
 C69B-C70B
 1.3 with sigma of 0.02
 C70B-S7B
 1.71 with sigma of 0.02
 C65-C66
 1.3 with sigma of 0.02
 C68B-S8B
 1.71 with sigma of 0.02
 C67B-C68B
 1.34 with sigma of 0.02
 C62-C61
 1.36 with sigma of 0.01
 C68B-C67B
 1.36 with sigma of 0.02
 S6-C67A
 1.72 with sigma of 0.01
 N3-C20
 1.49 with sigma of 0.01
 N4-C35
 1.49 with sigma of 0.01
 N5-C40
 1.49 with sigma of 0.01
 N1-C58
 1.49 with sigma of 0.01
 N2-C15
 1.49 with sigma of 0.01
 C53-C0AA
 1.54 with sigma of 0.01
 C40-C8AA
 1.54 with sigma of 0.01
 C20-C2AA
 1.54 with sigma of 0.01
 C74-C73
 1.38 with sigma of 0.02
 C76-H76
 0.98 with sigma of 0.005
 C75-H75
 0.98 with sigma of 0.005
 S11-C76
 1.78 with sigma of 0.02
 C54-C3AA
 1.54 with sigma of 0.02
 C1AA-C18
 1.54 with sigma of 0.02
 C1AA-C16
 1.54 with sigma of 0.02
 C40-C35 \\sim C36-C37 \\sim C38-C39
 with sigma of 0.02
 C20-C15 \\sim C20-C19 \\sim C19-C18 \\sim C18-C17 \\sim C17-C16 \\sim C16-C15
 with sigma of 0.01
 C20-C19 \\sim C18-C17 \\sim C16-C15
 with sigma of 0.01
 N2-C15 \\sim N3-C20 \\sim N4-C35 \\sim N5-C40 \\sim C53-N6 \\sim C58-N1
 with sigma of 0.02
 C75-H75 \\sim C76-H76
 with sigma of 0.005
3. Restrained planarity
 S9, S10, C71, C72
 with sigma of 0.01
 S5A, S6, C65, C66
 with sigma of 0.01
 H75, C75, H76, C76
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
N6 \\sim N5: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
C75 \\sim C76: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
Uanis(C74) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.1
Uanis(C67A) \\sim Ueq, Uanis(C67B) \\sim Ueq, Uanis(C68B) \\sim Ueq,
Uanis(C68A) \\sim Ueq, Uanis(C69B) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.1
Uanis(C58) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.1
Uanis(C66) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.1
Uanis(C70A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.1
Uanis(C17) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.1
Uanis(C48) \\sim Ueq, Uanis(C49) \\sim Ueq, Uanis(C1DA) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.1
Uanis(C69A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.1
Uanis(C70B) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.1
Uanis(C4AA) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.1
Uanis(C71) \\sim Ueq, Uanis(C72) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.1
Uanis(C67B) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.1
Uanis(C1AA) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.1
Uanis(C24) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.1
Uanis(C2AA) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.1
Uanis(C73) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.2
Uanis(C36) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C2) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(N6) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C52) \\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(C15) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C46) \\sim Ueq, Uanis(C47) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
Uanis(C75) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C51) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C56) \\sim Ueq, Uanis(C3AA) \\sim Ueq, Uanis(C97) \\sim Ueq: with sigma
of 0.02 and sigma for terminal atoms of 0.02
Uanis(C12) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.02
Uanis(C35) \\sim Ueq, Uanis(C68) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.02
Uanis(C38) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C5AA) \\sim Ueq, Uanis(C38) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.02
Uanis(O7) \\sim Ueq: with sigma of 0.025 and sigma for terminal atoms of 0.025
Uanis(C55) \\sim Ueq, Uanis(C56) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.02
Uanis(C50) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.02
Uanis(O11) = Uanis(O12)
5. Others
 Fixed Sof: C15(0.5) H15(0.5) H16A(0.5) H16B(0.5) H16C(0.5) H16D(0.5) C17(0.5)
 H17A(0.5) H17B(0.5) H18A(0.5) H18B(0.5) H18C(0.5) H18D(0.5) H20(0.5) H20A(0.5)
 C35(0.5) H35(0.5) H36A(0.5) H36B(0.5) H36C(0.5) H36D(0.5) C37(0.5) H37A(0.5)
 H37B(0.5) C38(0.5) H38A(0.5) H38B(0.5) H39A(0.5) H39B(0.5) H39C(0.5) H39D(0.5)
 H40(0.5) H40A(0.5) H53(0.5) H53A(0.5) H54C(0.5) H54D(0.5) H54A(0.5) H54B(0.5)
 C55(0.5) H55A(0.5) H55B(0.5) C56(0.5) H56A(0.5) H56B(0.5) H57A(0.5) H57B(0.5)
 H57C(0.5) H57D(0.5) C58(0.5) H58(0.5) S5A(0.5) S7A(0.5) S8A(0.5) C67A(0.5)
 C68A(0.5) C69A(0.5) H69A(0.5) C70A(0.5) H70A(0.5) C67B(0.5) S8B(0.5) C70B(0.5)
 H70B(0.5) S7B(0.5) C69B(0.5) H69B(0.5) S5B(0.5) C68B(0.5) S9(0.5) S10(0.5)
 C71(0.5) H71(0.5) C72(0.5) H72(0.5) C73(0.5) C74(0.5) S11(0.5) S12(0.5)
 C0AA(0.5) H0AA(0.5) C1AA(0.5) H1AA(0.5) H1AB(0.5) C2AA(0.5) H2AA(0.5)
 C8AA(0.5) H8AA(0.5) C76(0.5) C75(0.5) C97(0.5) H97A(0.5) H97B(0.5) C3AA(0.5)
 H3AA(0.5) H3AB(0.5) C68(0.5) H68A(0.5) H68B(0.5) C5AA(0.5) H5AA(0.5) H5AB(0.5)
6.a Ternary CH refined with riding coordinates:
 C15(H15), C20(H20), C20(H20A), C35(H35), C40(H40), C40(H40A), C53(H53),
 C53(H53A), C58(H58), C0AA(H0AA), C2AA(H2AA), C8AA(H8AA)
6.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C16(H16C,H16D), C17(H17A,H17B), C18(H18A,H18B), C18(H18C,
 H18D), C19(H19A,H19B), C36(H36A,H36B), C36(H36C,H36D), C37(H37A,H37B),
 C38(H38A,H38B), C39(H39A,H39B), C39(H39C,H39D), C54(H54C,H54D), C54(H54A,H54B),
  C55(H55A,H55B), C56(H56A,H56B), C57(H57A,H57B), C57(H57C,H57D), C1AA(H1AA,
 H1AB), C97(H97A,H97B), C3AA(H3AA,H3AB), C68(H68A,H68B), C5AA(H5AA,H5AB)
6.c Aromatic/amide H refined with riding coordinates:
 C1DA(H1DA), C5BA(H5BA), C6(H6), C7(H7), C7AA(H7AA), C11(H11), C12(H12),
 C26(H26), C27(H27), C32(H32), C46(H46), C47(H47), C65(H65), C66(H66),
 C69A(H69A), C70A(H70A), C59(H59), C60(H60), C63(H63), C64(H64), C70B(H70B),
 C69B(H69B), C71(H71), C72(H72)
;
_shelx_res_checksum              68212
_shelx_hkl_checksum              67074
_shelx_fab_checksum              44082
_olex2_submission_special_instructions 'No special instructions were received'