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_4122941
_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_formula_moiety         'C60 H42 N6 O12, 0.5(C2 H4 Cl2)'
_chemical_formula_sum            'C61 H44 Cl N6 O12'
_chemical_formula_weight         1088.47
_chemical_name_systematic
;
 ?
;
_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     direct
_audit_creation_date             2013-10-02
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.025(2)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   46.2752(15)
_cell_length_b                   16.1173(5)
_cell_length_c                   40.4255(14)
_cell_measurement_reflns_used    9023
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      50.066
_cell_measurement_theta_min      2.902
_cell_volume                     30150.6(17)
_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
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100.07
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.577
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0384
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_Laue_measured_fraction_full 0.577
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            66099
_diffrn_reflns_point_group_measured_fraction_full 0.478
_diffrn_reflns_point_group_measured_fraction_max 0.821
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         50.55
_diffrn_reflns_theta_min         1.09
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.872
_exptl_absorpt_correction_T_max  0.7500
_exptl_absorpt_correction_T_min  0.5892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0650 before and 0.0467 after correction.
The Ratio of minimum to maximum transmission is 0.7856.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.959
_exptl_crystal_description       block
_exptl_crystal_F_000             9040
_exptl_crystal_size_max          0.382
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 5635 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.241(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2881
_refine_ls_number_reflns         26104
_refine_ls_number_restraints     6257
_refine_ls_restrained_S_all      1.201
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0651
_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^)+(0.1274P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1802
_refine_ls_wR_factor_ref         0.1923
_reflns_Friedel_coverage         0.596
_reflns_Friedel_fraction_full    0.371
_reflns_Friedel_fraction_max     0.643
_reflns_number_gt                17918
_reflns_number_total             26104
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja509480u_si_002.cif
_cod_data_source_block           n3024b
_cod_database_code               4122941
_shelxl_version_number           2012-9
_shelx_estimated_absorpt_t_max   0.926
_shelx_estimated_absorpt_t_min   0.732
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 O1-C7 \\sim O10-C52 \\sim O4-C18 \\sim O11-C53 \\sim O12-C58 \\sim O2-C12
\\sim O5-C27 \\sim O9-C47 \\sim O7-
 C33 \\sim O6-C32 \\sim O8-C38 \\sim O3-C13 \\sim O5A-C27A \\sim O3A-C13A \\sim
O8A-C38A \\sim O2A-C12A -
 O6A-C32A \\sim O7A-C33A \\sim O4A-C18A \\sim O12A-C58A \\sim O9A-C47A \\sim
O10A-C52A \\sim O11A-C53A
 \\sim O1A-C7A \\sim O4B-C18B \\sim O7B-C33B \\sim O8B-C38B \\sim O3B-C13B
\\sim O5B-C27B \\sim O2B-C12B -
 O1B-C7B \\sim O6B-C32B \\sim O10B-C52B \\sim O9B-C47B \\sim O12B-C58B \\sim
O11B-C53B \\sim O12C-C58C
 \\sim O7C-C33C \\sim O6C-C32C \\sim O9C-C47C \\sim O5C-C27C \\sim O11C-C53C
\\sim O3C-C13C \\sim O8C-C38C
 \\sim O4C-C18C \\sim O1C-C7C \\sim O2C-C12C \\sim O10C-C52C
 with sigma of 0.01
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.005
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.01 and sigma
for terminal atoms of 0.02
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.01 and sigma
for terminal atoms of 0.01
5. Rigid body (RIGU) restrains
 O2C, O3C
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
6.a Ternary CH refined with riding coordinates:
 C1(H), C6(HI), C21(HN), C26(HW), C41(H1AA), C46(H0BA), C1A(H5BA), C6A(H8CA),
 C21A(H3DA), C26A(H2EA), C41A(H7EA), C46A(H6FA), C1B(H1GA), C6B(H0HA),
 C21B(H5HA), C26B(H4IA), C41B(H9IA), C46B(H8JA), C1C(H1C), C6C(H6C), C21C(H21C),
  C26C(H26C), C41C(H41C), C46C(H46C)
6.b Secondary CH2 refined with riding coordinates:
 C2(HA,HB), C3(HC,HD), C4(HE,HF), C5(HG,HH), C22(HO,HP), C23(HQ,HR), C24(HS,
 HT), C25(HU,HV), C42(H2AA,H3AA), C43(H4AA,H5AA), C44(H6AA,H7AA), C45(H8AA,
 H9AA), C2A(H6BA,H7BA), C3A(H8BA,H9BA), C4A(H0CA,H1CA), C5A(H6CA,H7CA),
 C22A(H4DA,H5DA), C23A(H6DA,H7DA), C24A(H8DA,H9DA), C25A(H0EA,H1EA), C42A(H8EA,
 H9EA), C43A(H0FA,H1FA), C44A(H2FA,H3FA), C45A(H4FA,H5FA), C2B(H2GA,H3GA),
 C3B(H4GA,H5GA), C4B(H6GA,H7GA), C5B(H8GA,H9GA), C22B(H6HA,H7HA), C23B(H8HA,
 H9HA), C24B(H0IA,H1IA), C25B(H2IA,H3IA), C42B(H0JA,H1JA), C43B(H2JA,H3JA),
 C44B(H4JA,H5JA), C45B(H6JA,H7JA), C2C(H2CA,H2CB), C3C(H3CA,H3CB), C4C(H4CA,
 H4CB), C5C(H5CA,H5CB), C22C(H22A,H22B), C23C(H23A,H23B), C24C(H24A,H24B),
 C25C(H25A,H25B), C42C(H42A,H42B), C43C(H43A,H43B), C44C(H44A,H44B), C45C(H45A,
 H45B), C61(H3KA,H4KA), C62(H5KA,H6KA), C63(H7KA,H8KA), C64(H9KA,H0LA)
6.c Aromatic/amide H refined with riding coordinates:
 C9(HJ), C10(HK), C15(HL), C16(HM), C29(HX), C30(HY), C35(HZ), C36(H0AA),
 C49(H1BA), C50(H2BA), C55(H3BA), C56(H4BA), C9A(H9CA), C10A(H0DA), C15A(H1DA),
 C16A(H2DA), C29A(H3EA), C30A(H4EA), C35A(H5EA), C36A(H6EA), C49A(H7FA),
 C50A(H8FA), C55A(H9FA), C56A(H0GA), C9B(H1HA), C10B(H2HA), C15B(H3HA),
 C16B(H4HA), C29B(H5IA), C30B(H6IA), C35B(H7IA), C36B(H8IA), C49B(H9JA),
 C50B(H0KA), C55B(H1KA), C56B(H2KA), 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 = 13337.7 Ang^3^ [44.2%]
Total electron count / cell = 3900.7
;
_shelx_res_checksum              15973
_shelx_hkl_checksum              17560