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_4122940
_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         '3(C2 H4 Br2), C60 H42 N6 O12'
_chemical_formula_sum            'C66 H54 Br6 N6 O12'
_chemical_formula_weight         1602.61
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2013-06-14
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                119.5499(16)
_cell_angle_beta                 100.2052(18)
_cell_angle_gamma                92.9355(18)
_cell_formula_units_Z            2
_cell_length_a                   15.7342(6)
_cell_length_b                   16.0668(6)
_cell_length_c                   16.1856(6)
_cell_measurement_reflns_used    9885
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.49
_cell_measurement_theta_min      5.79
_cell_volume                     3457.0(2)
_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
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      99.97
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.911
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Quazar optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.911
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13977
_diffrn_reflns_point_group_measured_fraction_full 0.558
_diffrn_reflns_point_group_measured_fraction_max 0.596
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         64.89
_diffrn_reflns_theta_min         2.89
_diffrn_source                   microsource
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.713
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6674
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0470 before and 0.0369 after correction.
The Ratio of minimum to maximum transmission is 0.8868.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_description       block
_exptl_crystal_F_000             1596
_exptl_crystal_size_max          0.142
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.055
_refine_diff_density_max         1.163
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.122
_refine_ls_abs_structure_details
;
 Flack x determined using 2304 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.194(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1640
_refine_ls_number_reflns         13977
_refine_ls_number_restraints     1593
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0525
_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^)+(0.1051P)^2^+5.1009P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1458
_refine_ls_wR_factor_ref         0.1478
_reflns_Friedel_coverage         0.224
_reflns_Friedel_fraction_full    0.204
_reflns_Friedel_fraction_max     0.218
_reflns_number_gt                13203
_reflns_number_total             13977
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja509480u_si_005.cif
_cod_data_source_block           n2833
_cod_database_code               4122940
_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. Uiso/Uaniso restraints and constraints
Uanis(C24) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C71) \\sim Ueq, Uanis(C37) \\sim Ueq, Uanis(C53) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.02
3. Others
 Sof(Br2A)=Sof(C32A)=Sof(H32A)=Sof(H32B)=Sof(H13C)=Sof(H13D)=1-FVAR(1)
 Sof(Br12)=Sof(H13A)=Sof(H13B)=Sof(C132)=Sof(H13E)=Sof(H13F)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C15(H15), C20(H20), C35(H35), C40(H40), C55(H55), C60(H60), C75(H75),
 C80(H80), C94(H94), C99(H99), C114(H114), C119(H119)
4.b Secondary CH2 refined with riding coordinates:
 C121(H12A,H12B), C122(H12C,H12D), C32A(H32A,H32B), C131(H13C,H13D), C131(H13A,
 H13B), C132(H13E,H13F), C123(H12E,H12F), C124(H12G,H12H), C125(H12I,H12J),
 C126(H12K,H12L), C127(H12M,H12N), C128(H12O,H12P), C129(H12Q,H12R), C130(H13G,
 H13H), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B),
 C36(H36A,H36B), C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B), C56(H56A,H56B),
  C57(H57A,H57B), C58(H58A,H58B), C59(H59A,H59B), C76(H76A,H76B), C77(H77A,
 H77B), C78(H78A,H78B), C79(H79A,H79B), C95(H95A,H95B), C96(H96A,H96B),
 C97(H97A,H97B), C98(H98A,H98B), C115(H11A,H11B), C116(H11C,H11D), C117(H11E,
 H11F), C118(H11G,H11H)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C9(H9), C10(H10), C23(H23), C24(H24), C29(H29), C30(H30),
 C43(H43), C44(H44), C49(H49), C50(H50), C63(H63), C64(H64), C69(H69), C70(H70),
  C83(H83), C84(H84), C89(H89), C90(H90), C102(H102), C103(H103), C108(H108),
 C109(H109)
;
_smtbx_masks_special_details
;
Total solvent accessible volume / cell = 527.9 Ang^3^ [15.3%]
Total electron count / cell = 38.0

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.
;
_shelx_estimated_absorpt_t_max   0.782
_shelx_estimated_absorpt_t_min   0.554
_shelx_hkl_checksum              61620
_shelx_res_checksum              56367
_shelxl_version_number           2012-9