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_4127312
_publ_section_title
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 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         '3(C6 H4 S4), C60 H42 N6 O12, 1(C H2 Cl2)'
_chemical_formula_sum            'C79 H52 Cl2 N6 O12 S12'
_chemical_formula_weight         1732.88
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-07-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-24 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 91.229(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.1136(10)
_cell_length_b                   15.6480(9)
_cell_length_c                   27.3059(15)
_cell_measurement_reflns_used    9498
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.454
_cell_measurement_theta_min      3.740
_cell_volume                     7737.8(7)
_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      99.99
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.945
_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  0.1025
_diffrn_reflns_av_unetI/netI     0.1045
_diffrn_reflns_Laue_measured_fraction_full 0.945
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            37431
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        65.402
_diffrn_reflns_theta_max         65.402
_diffrn_reflns_theta_min         3.255
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.339
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1034 before and 0.0737 after correction. The Ratio of minimum to maximum transmission is 0.6191. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_description       Needle
_exptl_crystal_F_000             3560
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.061
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.779
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.128
_refine_ls_extinction_coef       9891(122)
_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   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1077
_refine_ls_number_reflns         12570
_refine_ls_number_restraints     277
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.2057
_refine_ls_R_factor_gt           0.1947
_refine_ls_shift/su_max          0.929
_refine_ls_shift/su_mean         0.012
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+45.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3720
_refine_ls_wR_factor_ref         0.3780
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10990
_reflns_number_total             12570
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b08758_si_007.cif
_cod_data_source_block           yb058j
_cod_database_code               4127312
_publcif_datablock.id            {07854da5-e58b-4c6c-a784-0a52f1e336c3}
_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
 Cl2-C79
 1.78 with sigma of 0.02
 C80-Cl4
 1.78 with sigma of 0.02
 Cl3-C80
 1.78 with sigma of 0.02
 C79-Cl1
 1.78 with sigma of 0.02
 S8-C72
 1.76 with sigma of 0.02
 C71-C72
 1.36 with sigma of 0.02
 S10-C75
 1.76 with sigma of 0.02
 C78-C77
 1.36 with sigma of 0.02
 C47-C46
 1.36 with sigma of 0.02
 C49-C50
 1.54 with sigma of 0.01
 C44-C43
 1.54 with sigma of 0.01
 C56-C55
 1.54 with sigma of 0.02
 C45-C46
 1.54 with sigma of 0.02
 C48-C47
 1.54 with sigma of 0.02
 C43-C48
 1.54 with sigma of 0.02
 C44-C45
 1.54 with sigma of 0.02
 C52-C53
 1.54 with sigma of 0.02
 C51-C52
 1.54 with sigma of 0.02
 C54-C53
 1.54 with sigma of 0.02
 C56-C57
 1.54 with sigma of 0.02
 C58-C59
 1.54 with sigma of 0.02
 C60-C55
 1.54 with sigma of 0.02
 S10-C73
 1.76 with sigma of 0.02
 C75-S9
 1.76 with sigma of 0.02
 C75-S10
 1.76 with sigma of 0.02
 S9-C74
 1.76 with sigma of 0.02
 S4-C66
 1.76 with sigma of 0.02
 C75-C73
 2.6 with sigma of 0.02
 S11-C77
 1.76 with sigma of 0.02
 C64-C63
 1.36 with sigma of 0.02
 C76-C75
 1.36 with sigma of 0.02
 S5-C69
 1.72 with sigma of 0.02
 C69-S6
 1.72 with sigma of 0.02
 C49-C54
 1.54 with sigma of 0.02
 C53-C52
 1.54 with sigma of 0.02
 C51-C50
 1.54 with sigma of 0.02
 C46-C47
 1.54 with sigma of 0.02
 C0AA-Cl0A
 1.78 with sigma of 0.02
 C15-O5
 1.24 with sigma of 0.02
 Cl18-C0AA
 1.78 with sigma of 0.02
 Cl1-Cl2
 2.6 with sigma of 0.02
 C42-O12
 1.24 with sigma of 0.02
 N1-C44
 1.48 with sigma of 0.02
 N6-C43
 1.48 with sigma of 0.02
 C56-N5
 1.48 with sigma of 0.02
 C55-N4
 1.48 with sigma of 0.02
 N3-C50
 1.48 with sigma of 0.02
 C49-N2
 1.48 with sigma of 0.02
 C1AA-C2AA
 1.54 with sigma of 0.02
 C2AA-C1AA
 1.54 with sigma of 0.02
 C54-C2AA
 1.54 with sigma of 0.02
 N2-C2AA
 1.48 with sigma of 0.02
 C44-C3AA
 1.55 with sigma of 0.02
3. Restrained angles
 C75-S10-C73
 fixed at 0.66 with sigma of 0.02
4. Restrained planarity
 S10, C73, C74, S9
 with sigma of 0.01
 S5, C67, C68, S6
 with sigma of 0.005
5. Uiso/Uaniso restraints and constraints
Cl0A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(C52) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.1
Uanis(C50) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.1
Uanis(C55) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.1
Uanis(Cl2) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.1
Uanis(C73) \\sim Ueq, Uanis(C74) \\sim Ueq: with sigma of 0.025 and sigma for
terminal atoms of 0.1
Uanis(C79) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.1
Uanis(Cl1) \\sim Ueq: with sigma of 0.25 and sigma for terminal atoms of 0.1
Uanis(C72) \\sim Ueq: with sigma of 0.025 and sigma for terminal atoms of 0.1
Uanis(C47) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.1
Uanis(Cl4) \\sim Ueq: with sigma of 0.025 and sigma for terminal atoms of 0.1
Uanis(Cl3) \\sim Ueq: with sigma of 0.025 and sigma for terminal atoms of 0.2
Uanis(C80) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.1
Uanis(C75) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.02
Uanis(C0AA) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.02
Uanis(C68) \\sim Ueq, Uanis(C67) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
Uanis(C2AA) \\sim Ueq, Uanis(C49) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
Uanis(C1AA) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C3AA) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
6. Rigid body (RIGU) restrains
 C44, C43, C48, C47, C46, C45
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C49, C54, C53, C52, C51, C50
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C56, C57, C58, C59, C60, C55
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C46, C47, C48, C43, C44, C45
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C50, C51, C52, C53, C54, C49
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
7. Others
 Fixed Sof: H51A(0.5) H51B(0.5) H51D(0.5) H51C(0.5) H54D(0.5) H54C(0.5)
 H54B(0.5) H54A(0.5) C43(0.5) H43(0.5) H44(0.5) H44A(0.5) H48A(0.5) H48B(0.5)
 H48C(0.5) H48D(0.5) C50(0.5) H50(0.5) C49(0.5) H49(0.5) Cl2(0.33333)
 C79(0.33333) H79A(0.33333) H79B(0.33333) Cl1(0.33333) C80(0.33333)
 H80A(0.33333) H80B(0.33333) Cl3(0.33333) Cl4(0.33333) C0AA(0.33333)
 H0AA(0.33333) H0AB(0.33333) Cl0A(0.33333) Cl18(0.33333) C1AA(0.5) H1AA(0.5)
 C2AA(0.5) H2AA(0.5) C3AA(0.5) H3AA(0.5)
8.a Ternary CH refined with riding coordinates:
 C43(H43), C44(H44), C44(H44A), C56(H56), C50(H50), C49(H49), C55(H55),
 C1AA(H1AA), C2AA(H2AA), C3AA(H3AA)
8.b Secondary CH2 refined with riding coordinates:
 C57(H57A,H57B), C60(H60A,H60B), C53(H53A,H53B), C51(H51A,H51B), C51(H51D,
 H51C), C54(H54D,H54C), C54(H54B,H54A), C59(H59A,H59B), C58(H58A,H58B),
 C45(H45A,H45B), C46(H46A,H46B), C47(H47A,H47B), C48(H48A,H48B), C48(H48C,H48D),
  C52(H52A,H52B), C79(H79A,H79B), C80(H80A,H80B), C0AA(H0AA,H0AB)
8.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C7(H7), C35(H35), C6(H6), C36(H36), C20(H20), C34(H34),
 C37(H37), C25(H25), C21(H21), C26(H26), C66(H66), C62(H62), C78(H78), C61(H61),
  C68(H68), C71(H71), C67(H67), C65(H65), C72(H72), C77(H77), C73(H73), C74(H74)
;
_shelx_res_checksum              34593
_shelx_hkl_checksum              65732
_olex2_submission_special_instructions 'No special instructions were received'