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_4127311
_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_formula_moiety         'C60 H42 N6 O12, C4 H10 O, C2 H3 N'
_chemical_formula_sum            'C66 H55 N7 O13'
_chemical_formula_weight         1154.17
_space_group_crystal_system      hexagonal
_space_group_IT_number           171
_space_group_name_Hall           'P 62'
_space_group_name_H-M_alt        'P 62'
_symmetry_space_group_name_Hall  'P 62'
_symmetry_space_group_name_H-M   'P 62'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   34.5345(11)
_cell_length_b                   34.5345(11)
_cell_length_c                   8.5499(4)
_cell_measurement_reflns_used    3296
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      54.23
_cell_measurement_theta_min      4.44
_cell_volume                     8830.8(6)
_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    'XM (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.95
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            24922
_diffrn_reflns_point_group_measured_fraction_full 0.851
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.257
_diffrn_reflns_theta_min         4.435
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.756
_exptl_absorpt_correction_T_max  0.7507
_exptl_absorpt_correction_T_min  0.5912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1206 before and 0.0542 after correction.
The Ratio of minimum to maximum transmission is 0.7875.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       Needle
_exptl_crystal_F_000             3624
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.894
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     820
_refine_ls_number_reflns         9124
_refine_ls_number_restraints     40
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0706
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1375P)^2^+1.9675P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1908
_refine_ls_wR_factor_ref         0.2038
_reflns_Friedel_coverage         0.596
_reflns_Friedel_fraction_full    0.688
_reflns_Friedel_fraction_max     0.680
_reflns_number_gt                7558
_reflns_number_total             9124
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b08758_si_004.cif
_cod_data_source_block           yb064nuz1
_cod_original_cell_volume        8830.8(7)
_cod_database_code               4127311
_publcif_datablock.id            {509085f9-d923-4d6c-a0ae-46175e484a2a}
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.952
_shelx_estimated_absorpt_t_min   0.727
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.2(4)
 -0.2(4)
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
 N7-C66
 1.2 with sigma of 0.02
 C69-C70
 1.54 with sigma of 0.02
 C69-N8
 1.2 with sigma of 0.02
 N8-C68
 1.2 with sigma of 0.02
 C68-C67
 1.54 with sigma of 0.02
 C64-C63
 1.54 with sigma of 0.01
 C62-C61
 1.54 with sigma of 0.01
 O13-C62
 1.43 with sigma of 0.01
 C63-O13
 1.43 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
C63 \\sim C62: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
Uanis(C69) \\sim Ueq, Uanis(C70) \\sim Ueq, Uanis(C67) \\sim Ueq: with sigma of
0.025 and sigma for terminal atoms of 0.1
Uanis(C63) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C64) \\sim Ueq: with sigma of 0.015 and sigma for terminal atoms of 0.01
Uanis(C67) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
5. Others
 Fixed Sof: N7(0.5) C65(0.5) H65A(0.5) H65C(0.5) H65B(0.5) C66(0.5) C68(0.25)
 C70(0.25) H70A(0.25) H70B(0.25) H70C(0.25) N8(0.5) C69(0.25) C67(0.25)
 H67A(0.25) H67B(0.25) H67C(0.25)
 Fixed U11: C68(0.192)
 Fixed U12: C68(-0.030045)
 Fixed U13: C68(0.064548)
 Fixed U22: C68(0.13776)
 Fixed U23: C68(-0.03458)
 Fixed U33: C68(0.11779)
6.a Ternary CH refined with riding coordinates:
 C56(H56), C43(H43), C55(H55), C48(H48), C50(H50), C49(H49)
6.b Secondary CH2 refined with riding coordinates:
 C44(H44A,H44B), C57(H57A,H57B), C60(H60A,H60B), C47(H47A,H47B), C51(H51A,
 H51B), C59(H59A,H59B), C58(H58A,H58B), C45(H45A,H45B), C46(H46A,H46B),
 C52(H52A,H52B), C54(H54A,H54B), C62(H62A,H62B), C53(H53A,H53B), C63(H63A,H63B)
6.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C20(H20), C25(H25), C26(H26), C6(H6), C7(H7), C12(H12), C11(H11),
 C33(H33), C38(H38), C34(H34), C39(H39)
6.d Idealised Me refined as rotating group:
 C61(H61A,H61B,H61C), C64(H64A,H64B,H64C), C65(H65A,H65C,H65B), C70(H70A,H70B,
 H70C), C67(H67A,H67B,H67C)
;
_shelx_res_checksum              1802
_shelx_hkl_checksum              40690
_shelx_fab_checksum              99619
_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
;
;