Assembly of Supramolecular Nanotubes from Molecular Triangles and 1,2-Dihalohydrocarbons.
Liu, Zhichang; Liu, Guoliang; Wu, Yilei; Cao, Dennis; Sun, Junling; Schneebeli, Severin T.; Nassar, Majed S.; Mirkin, Chad A.; Stoddart, J. Fraser; Journal of the American Chemical Society  (2014) 141114095931006–; doi:10.1021/ja509480u

data_4122942
_publ_section_title
;
 Assembly of Supramolecular Nanotubes from Molecular Triangles and
 1,2-Dihalohydrocarbons.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              141114095931006
_journal_paper_doi               10.1021/ja509480u
_journal_year                    2014
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C60 H42 N6 O12'
_chemical_formula_sum            'C60 H42 N6 O12'
_chemical_formula_weight         1038.99
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2013-12-13
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.6571(12)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   46.8926(8)
_cell_length_b                   16.3192(3)
_cell_length_c                   40.7083(7)
_cell_measurement_reflns_used    9644
_cell_measurement_temperature    240(2)
_cell_measurement_theta_max      63.553
_cell_measurement_theta_min      2.892
_cell_volume                     31150.0(9)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.1-4 (Bruker, 2007)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_diffrn_ambient_temperature      240.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.934
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Quazar optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 0.934
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       54
_diffrn_reflns_limit_h_min       -54
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            156519
_diffrn_reflns_point_group_measured_fraction_full 0.917
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         65.174
_diffrn_reflns_theta_min         2.185
_diffrn_source                   microsource
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.519
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6023
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0607 before and 0.0467 after correction.
The Ratio of minimum to maximum transmission is 0.8003.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.886
_exptl_crystal_description       tabular
_exptl_crystal_F_000             8640
_exptl_crystal_size_max          0.402
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.07(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2809
_refine_ls_number_reflns         51762
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0523
_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^)+(0.0766P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1349
_refine_ls_wR_factor_ref         0.1440
_reflns_Friedel_coverage         0.892
_reflns_Friedel_fraction_full    0.899
_reflns_Friedel_fraction_max     0.954
_reflns_number_gt                33069
_reflns_number_total             51762
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja509480u_si_003.cif
_cod_data_source_block           n3208a
_cod_database_code               4122942
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.818
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C6(H6), C21(H21), C26(H26), C41(H41), C46(H46), C1A(H1A), C6A(H6A),
 C21A(H21A), C26A(H26A), C41A(H41A), C46A(H46A), C1B(H1B), C6B(H6B), C21B(H21B),
  C26B(H26B), C41B(H41B), C46B(H46B), C1C(H1C), C6C(H6C), C21C(H21C),
 C26C(H26C), C41C(H41C), C46C(H46C)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C22(H22A,H22B), C23(H23A,
 H23B), C24(H24A,H24B), C25(H25A,H25B), C42(H42A,H42B), C43(H43A,H43B),
 C44(H44A,H44B), C45(H45A,H45B), C2A(H2AA,H2AB), C3A(H3AA,H3AB), C4A(H4AA,H4AB),
  C5A(H5AA,H5AB), C22A(H22C,H22D), C23A(H23C,H23D), C24A(H24C,H24D), C25A(H25C,
 H25D), C42A(H42C,H42D), C43A(H43C,H43D), C44A(H44C,H44D), C45A(H45C,H45D),
 C2B(H2BA,H2BB), C3B(H3BA,H3BB), C4B(H4BA,H4BB), C5B(H5BA,H5BB), C22B(H22E,
 H22F), C23B(H23E,H23F), C24B(H24E,H24F), C25B(H25E,H25F), C42B(H42E,H42F),
 C43B(H43E,H43F), C44B(H44E,H44F), C45B(H45E,H45F), C2C(H2CA,H2CB), C3C(H3CA,
 H3CB), C4C(H4CA,H4CB), C5C(H5CA,H5CB), C22C(H22G,H22H), C23C(H23G,H23H),
 C24C(H24G,H24H), C25C(H25G,H25H), C42C(H42G,H42H), C43C(H43G,H43H), C44C(H44G,
 H44H), C45C(H45G,H45H)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C15(H15), C16(H16), C29(H29), C30(H30), C35(H35), C36(H36),
 C49(H49), C50(H50), C55(H55), C56(H56), C9A(H9A), C10A(H10A), C15A(H15A),
 C16A(H16A), C29A(H29A), C30A(H30A), C35A(H35A), C36A(H36A), C49A(H49A),
 C50A(H50A), C55A(H55A), C56A(H56A), C9B(H9B), C10B(H10B), C15B(H15B),
 C16B(H16B), C29B(H29B), C30B(H30B), C35B(H35B), C36B(H36B), C49B(H49B),
 C50B(H50B), C55B(H55B), C56B(H56B), C9C(H9C), C10C(H10C), C15C(H15C),
 C16C(H16C), C29C(H29C), C30C(H30C), C35C(H35C), C36C(H36C), C49C(H49C),
 C50C(H50C), C55C(H55C), C56C(H56C)
;
_smtbx_masks_special_details
;
The solvent masking procedure as implemented in Olex2 was used to remove the
electronic contribution of solvent molecules from the refinement.  As the exact
solvent content is not known, only the atoms used in the refinement model are
reported in the formula here.

Total solvent accessible volume / cell = 15542.9 Ang^3^ [49.9%]
Total electron count / cell = 3942.5
;
_shelx_res_checksum              72677
_shelx_hkl_checksum              14169