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_4127310
_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 rm
_chemical_formula_moiety         'C60 H42 N6 O12, C4 H10 O'
_chemical_formula_sum            'C64 H52 N6 O13'
_chemical_formula_weight         1113.11
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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
_audit_creation_date             2019-07-19
_audit_creation_method
;
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

;
_cell_angle_alpha                62.204(7)
_cell_angle_beta                 85.045(8)
_cell_angle_gamma                77.442(7)
_cell_formula_units_Z            2
_cell_length_a                   8.731(3)
_cell_length_b                   18.330(6)
_cell_length_c                   18.881(6)
_cell_measurement_reflns_used    2964
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      19.42
_cell_measurement_theta_min      2.28
_cell_volume                     2608.7(15)
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.16
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_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  0.1813
_diffrn_reflns_av_unetI/netI     0.3502
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            51932
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.493
_diffrn_reflns_theta_min         2.138
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1310 before and 0.0929 after correction.
The Ratio of minimum to maximum transmission is 0.7089.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       plate
_exptl_crystal_F_000             1164
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1469
_refine_ls_number_reflns         21111
_refine_ls_number_restraints     53
_refine_ls_restrained_S_all      0.976
_refine_ls_R_factor_all          0.2764
_refine_ls_R_factor_gt           0.0997
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0788P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1748
_refine_ls_wR_factor_ref         0.2365
_reflns_Friedel_coverage         0.980
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                7972
_reflns_number_total             21111
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {0f65a9b0-bd0d-4ae2-a315-5dc84495518f}
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
_cod_data_source_file            ja9b08758_si_003.cif
_cod_data_source_block           yb_008f_a
_cod_original_cell_volume        2608.7(14)
_cod_database_code               4127310
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.987
_olex2_refinement_description
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1. Twinned data refinement
 Scales: -1(2)
 2(2)
2. 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
3. Restrained distances
 C114-C115
 1.54 with sigma of 0.01
 C112-C113
 1.54 with sigma of 0.01
 C110-C111
 1.54 with sigma of 0.01
 C108-C109
 1.54 with sigma of 0.01
 O26-C108
 1.43 with sigma of 0.02
 O26-C110
 1.43 with sigma of 0.02
 O25-C112
 1.43 with sigma of 0.02
 O25-C114
 1.43 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C114) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.1
Uanis(C108) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.1
Uanis(C109) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.1
Uanis(O26) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.1
Uanis(C1) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.1
Uanis(N88) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C90) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(N88) = Uanis(N11)
Uanis(C77) = Uanis(C78)
Uanis(C81) = Uanis(C80)
Uanis(C5) = Uanis(C8)
Uanis(C41) = Uanis(C42)
5. Same fragment restrains
{C1, C2} sigma for 1-2: 0.02, 1-3: 0.04
as
{C1, C2}
6.a Ternary CH refined with riding coordinates:
 C43(H43), C44(H44), C49(H49), C50(H50), C55(H55), C56(H56), C90(H90),
 C91(H91), C96(H96), C97(H97), C102(H102), C103(H103)
6.b Secondary CH2 refined with riding coordinates:
 C45(H45A,H45B), C46(H46A,H46B), C47(H47A,H47B), C48(H48A,H48B), C51(H51A,
 H51B), C52(H52A,H52B), C53(H53A,H53B), C54(H54A,H54B), C57(H57A,H57B),
 C58(H58A,H58B), C59(H59A,H59B), C60(H60A,H60B), C92(H92A,H92B), C93(H93A,H93B),
  C94(H94A,H94B), C95(H95A,H95B), C98(H98A,H98B), C99(H99A,H99B), C100(H10A,
 H10B), C101(H10C,H10D), C104(H10E,H10F), C105(H10G,H10H), C106(H10I,H10J),
 C107(H10K,H10L), C108(H10M,H10N), C110(H11B,H11A), C112(H11F,H11G), C114(H11K,
 H11L)
6.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C8(H8), C12(H12), C20(H20), C21(H21), C24(H24), C25(H25),
 C34(H34), C35(H35), C36(H36), C40(H40), C66(H66), C67(H67), C71(H71), C72(H72),
  C80(H80), C81(H81), C83(H83), C84(H84), C121(H121), C122(H122), C123(H123),
 C125(H125)
6.d Idealised Me refined with everything fixed:
 C109(H10O,H10P,H10Q)
6.e Idealised Me refined as rotating group:
 C111(H11C,H11D,H11E), C113(H11H,H11I,H11J), C115(H11M,H11N,H11O)
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_shelx_res_checksum              28664
_shelx_hkl_checksum              19907
_shelx_fab_checksum              70409
_olex2_submission_special_instructions 'No special instructions were received'
_publcif_funding_html
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