#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:19:54 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180178 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/74/7107472.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7107472
loop_
_publ_author_name
'Shaoguang Li'
'Wei Meiying'
'Xiaojuan Huang'
'Xiao-Juan Yang'
'Biao Wu'
_publ_section_title
;
 Ion-pair induced self-assembly of molecular barrels with encapsulated
 tetraalkylammonium cations based on a bis-trisurea stave
;
_journal_name_full               Chem.Commun.
_journal_page_first              3097
_journal_paper_doi               10.1039/c2cc17699h
_journal_volume                  48
_journal_year                    2012
_chemical_formula_sum            'C108 H186 Br4 N18 O11'
_chemical_formula_weight         2232.39
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.945(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.2557(18)
_cell_length_b                   37.945(6)
_cell_length_c                   13.0316(19)
_cell_measurement_reflns_used    5980
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      50.93
_cell_measurement_theta_min      2.25
_cell_volume                     6015.8(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_sigmaI/netI    0.0728
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            39385
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.66
_exptl_absorpt_coefficient_mu    1.399
_exptl_absorpt_correction_T_max  0.8391
_exptl_absorpt_correction_T_min  0.6710
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Flack
_exptl_crystal_F_000             2376
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.811
_refine_diff_density_min         -0.613
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.688
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     659
_refine_ls_number_reflns         10560
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.692
_refine_ls_R_factor_all          0.1721
_refine_ls_R_factor_gt           0.1089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2730
_refine_ls_wR_factor_ref         0.2947
_reflns_number_gt                6046
_reflns_number_total             10560
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc17699h.txt
_cod_data_source_block           (TBA)4LBr4
_cod_original_cell_volume        6015.8(15)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7107472
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br2 Br 0.19825(8) 0.21852(2) 0.69107(7) 0.0748(4) Uani 1 1 d . . .
Br1 Br 0.00861(7) 0.09100(2) 0.19268(7) 0.0669(3) Uani 1 1 d . . .
N1 N 0.4587(16) -0.0382(5) 0.356(3) 0.26(3) Uani 0.58(3) 1 d PD A 1
O1 O 0.5503(16) -0.0383(8) 0.393(4) 0.33(3) Uani 0.50 1 d PD A 1
O2 O 0.3983(9) -0.0629(3) 0.3401(17) 0.305(12) Uani 0.58(3) 1 d PD A 1
N1A N 0.449(3) -0.0473(5) 0.272(2) 0.095(11) Uani 0.42(3) 1 d PD A 2
O1A O 0.529(4) -0.0540(9) 0.261(4) 0.25(3) Uani 0.42(3) 1 d P A 2
O2A O 0.3983(9) -0.0629(3) 0.3401(17) 0.305(12) Uani 0.42(3) 1 d P A 2
N2 N 0.2785(6) 0.08736(17) 0.1753(6) 0.080(2) Uani 1 1 d . . .
H2 H 0.2062 0.0881 0.1662 0.096 Uiso 1 1 calc R . .
N3 N 0.2632(5) 0.14485(15) 0.1237(5) 0.0599(17) Uani 1 1 d . . .
H3 H 0.1919 0.1409 0.1144 0.072 Uiso 1 1 calc R . .
N4 N 0.2112(6) 0.18220(15) -0.0741(5) 0.0597(17) Uani 1 1 d . . .
H4 H 0.2383 0.1840 -0.1334 0.072 Uiso 1 1 calc R . .
N5 N 0.0641(5) 0.16308(14) -0.1782(5) 0.0556(16) Uani 1 1 d . . .
H5 H 0.1056 0.1686 -0.2264 0.067 Uiso 1 1 calc R . .
N6 N -0.0304(5) 0.09813(14) -0.1090(5) 0.0534(16) Uani 1 1 d . . .
H6 H 0.0011 0.1086 -0.0528 0.064 Uiso 1 1 calc R . .
N7 N 0.0270(5) 0.04749(14) -0.0283(5) 0.0585(17) Uani 1 1 d . . .
H7 H 0.0469 0.0608 0.0261 0.070 Uiso 1 1 calc R . .
N9 N 0.1360(9) 0.0999(4) 0.5402(9) 0.160(6) Uani 1 1 d D . .
O3 O 0.4333(6) 0.12072(16) 0.1640(6) 0.096(2) Uani 1 1 d . . .
O4 O 0.0694(4) 0.15569(11) -0.0029(4) 0.0532(13) Uani 1 1 d . . .
O5 O -0.0508(4) 0.04578(13) -0.1954(4) 0.0631(14) Uani 1 1 d . . .
O6 O 0.0044(9) 0.9916(2) 0.6840(7) 0.059(3) Uani 0.50 1 d P . .
C1 C 0.4059(11) -0.0077(3) 0.2783(16) 0.198(10) Uani 1 1 d D . .
C2 C 0.2995(9) -0.0026(3) 0.2694(10) 0.113(4) Uani 1 1 d . A .
H2A H 0.2517 -0.0206 0.2883 0.136 Uiso 1 1 calc R . .
C3 C 0.2578(7) 0.0295(2) 0.2317(8) 0.080(3) Uani 1 1 d . . .
H3A H 0.1806 0.0333 0.2229 0.095 Uiso 1 1 calc R A .
C4 C 0.3258(8) 0.0555(2) 0.2073(9) 0.095(3) Uani 1 1 d . A .
C5 C 0.4338(11) 0.0488(4) 0.2181(18) 0.223(11) Uani 1 1 d . . .
H5A H 0.4827 0.0671 0.2036 0.268 Uiso 1 1 calc R A .
C6 C 0.4777(12) 0.0160(4) 0.250(2) 0.306(17) Uani 1 1 d . A .
H6A H 0.5537 0.0108 0.2507 0.367 Uiso 1 1 calc R . .
C7 C 0.3334(8) 0.1184(2) 0.1558(7) 0.072(2) Uani 1 1 d . . .
C8 C 0.3049(7) 0.17909(18) 0.1048(7) 0.058(2) Uani 1 1 d . . .
C9 C 0.3786(8) 0.1947(2) 0.1823(7) 0.076(3) Uani 1 1 d . . .
H9 H 0.3947 0.1837 0.2478 0.092 Uiso 1 1 calc R . .
C10 C 0.4282(8) 0.2268(2) 0.1619(9) 0.088(3) Uani 1 1 d . . .
H10 H 0.4793 0.2373 0.2136 0.106 Uiso 1 1 calc R . .
C11 C 0.4044(9) 0.2430(2) 0.0704(8) 0.079(3) Uani 1 1 d . . .
H11 H 0.4399 0.2645 0.0569 0.095 Uiso 1 1 calc R . .
C12 C 0.3298(8) 0.2287(2) -0.0025(8) 0.081(3) Uani 1 1 d . . .
H12 H 0.3121 0.2406 -0.0664 0.098 Uiso 1 1 calc R . .
C13 C 0.2773(7) 0.19617(18) 0.0138(6) 0.057(2) Uani 1 1 d . . .
C14 C 0.1132(6) 0.16670(17) -0.0776(7) 0.0493(19) Uani 1 1 d . . .
C15 C -0.0439(7) 0.15173(19) -0.2145(6) 0.059(2) Uani 1 1 d . . .
C16 C -0.1026(9) 0.1729(2) -0.2861(7) 0.080(3) Uani 1 1 d . . .
H16 H -0.0744 0.1954 -0.3010 0.096 Uiso 1 1 calc R . .
C17 C -0.2029(9) 0.1620(2) -0.3373(8) 0.094(3) Uani 1 1 d . . .
H17 H -0.2410 0.1762 -0.3899 0.113 Uiso 1 1 calc R . .
C18 C -0.2463(8) 0.1305(2) -0.3113(8) 0.091(3) Uani 1 1 d . . .
H18 H -0.3154 0.1230 -0.3452 0.109 Uiso 1 1 calc R . .
C19 C -0.1907(7) 0.1096(2) -0.2365(7) 0.076(3) Uani 1 1 d . . .
H19 H -0.2229 0.0881 -0.2178 0.091 Uiso 1 1 calc R . .
C20 C -0.0862(7) 0.11949(18) -0.1867(6) 0.058(2) Uani 1 1 d . . .
C21 C -0.0217(6) 0.06262(18) -0.1145(7) 0.054(2) Uani 1 1 d . . .
C22 C 0.0485(6) 0.00926(17) -0.0213(6) 0.056(2) Uani 1 1 d . . .
H22A H 0.1173 0.0048 0.0250 0.067 Uiso 1 1 calc R . .
H22B H 0.0575 -0.0002 -0.0906 0.067 Uiso 1 1 calc R . .
C23 C 0.2208(16) 0.0986(5) 0.4693(14) 0.183(9) Uani 1 1 d D . .
C24 C 0.3289(14) 0.1184(5) 0.5004(18) 0.32(2) Uani 1 1 d D . .
C25 C 0.4161(19) 0.1070(7) 0.428(3) 1.54(17) Uani 1 1 d D . .
C26 C 0.774(3) 0.1666(9) 0.223(3) 0.32(2) Uani 1 1 d . . .
C27 C 0.1785(15) 0.1027(7) 0.6543(11) 0.216(11) Uani 1 1 d . . .
C28 C 0.212(2) 0.0760(10) 0.708(3) 0.32(2) Uani 1 1 d . . .
C29 C 0.285(3) 0.0851(6) 0.838(3) 0.31(2) Uani 1 1 d . . .
C30 C 0.264(2) 0.0513(8) 0.846(3) 0.306(17) Uani 1 1 d . . .
C31 C 0.0393(16) 0.0756(6) 0.4919(15) 0.309(18) Uani 1 1 d D . .
C32 C -0.1694(16) 0.0670(7) 0.470(2) 0.44(3) Uani 1 1 d D . .
C33 C -0.0671(18) 0.0831(9) 0.5366(17) 0.75(8) Uani 1 1 d D . .
C34 C 0.1042(17) 0.1453(5) 0.502(2) 0.223(12) Uani 1 1 d . . .
C35 C 0.106(2) 0.1597(6) 0.3991(16) 0.248(14) Uani 1 1 d . . .
C36 C 0.071(2) 0.1978(7) 0.380(2) 0.235(11) Uani 1 1 d . . .
C37 C 0.0742(17) 0.2088(7) 0.2771(19) 0.220(10) Uani 1 1 d . . .
C38 C 0.8054(11) 0.1814(3) 0.0087(13) 0.149(6) Uani 1 1 d . . .
C39 C 0.7864(16) 0.2204(3) -0.0077(14) 0.198(10) Uani 1 1 d . . .
C40 C 0.925(3) 0.2362(4) 0.004(3) 0.33(2) Uani 1 1 d . . .
C41 C 0.928(4) 0.2510(11) -0.038(2) 0.45(4) Uani 1 1 d . . .
C42 C 0.5976(12) 0.1717(4) -0.0152(14) 0.148(6) Uani 1 1 d . . .
C43 C 0.5998(15) 0.1640(5) -0.1361(16) 0.206(8) Uani 1 1 d . . .
C44 C 0.4798(15) 0.1767(7) -0.1879(14) 0.204(11) Uani 1 1 d . . .
C45 C 0.4724(15) 0.1653(5) -0.294(3) 0.232(11) Uani 1 1 d . . .
C46 C 0.7406(8) 0.1249(3) 0.0365(11) 0.110(4) Uani 1 1 d . . .
C47 C 0.6543(11) 0.0991(3) 0.0724(14) 0.151(6) Uani 1 1 d . . .
C48 C 0.7052(15) 0.0613(4) 0.051(3) 0.239(15) Uani 1 1 d . . .
C49 C 0.656(3) 0.0413(8) 0.017(3) 0.35(2) Uani 1 1 d . . .
N8 N 0.7085(7) 0.1631(2) 0.0469(9) 0.105(3) Uani 1 1 d . . .
C51 C 0.6845(10) 0.1732(3) 0.1556(13) 0.112(4) Uani 1 1 d . . .
C52 C 0.751(4) 0.1797(11) 0.311(5) 0.52(6) Uani 1 1 d . . .
C53 C 0.756(5) 0.1679(15) 0.357(3) 0.50(5) Uani 1 1 d . . .
C54 C -0.170(2) 0.0270(6) 0.479(2) 1.48(13) Uani 1 1 d D . .
C50 C 0.520(4) 0.130(2) 0.451(6) 1.28(16) Uani 1 1 d D . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_3
O1 N1 O2 128(2) .
O1 N1 C1 123.4(16) .
O2 N1 C1 104.9(16) .
O1A N1A C1 124(3) .
C4 N2 C7 126.8(8) .
C7 N3 C8 119.9(7) .
C14 N4 C13 127.9(7) .
C14 N5 C15 128.9(7) .
C21 N6 C20 124.7(6) .
C21 N7 C22 122.2(6) .
C23 N9 C27 115.6(12) .
C23 N9 C31 106.4(11) .
C27 N9 C31 125.8(16) .
C23 N9 C34 90.2(15) .
C27 N9 C34 103.9(14) .
C31 N9 C34 108.6(12) .
C2 C1 C6 123.8(10) .
C2 C1 N1A 117.7(17) .
C6 C1 N1A 112.7(17) .
C2 C1 N1 118.5(13) .
C6 C1 N1 115.3(14) .
N1A C1 N1 41.4(15) .
C1 C2 C3 118.7(9) .
C4 C3 C2 120.8(9) .
C5 C4 C3 117.8(9) .
C5 C4 N2 124.8(9) .
C3 C4 N2 117.4(9) .
C4 C5 C6 122.7(12) .
C1 C6 C5 115.9(12) .
O3 C7 N3 124.6(8) .
O3 C7 N2 123.0(7) .
N3 C7 N2 112.3(8) .
C13 C8 C9 119.9(7) .
C13 C8 N3 121.8(7) .
C9 C8 N3 118.3(7) .
C8 C9 C10 119.2(9) .
C11 C10 C9 120.9(9) .
C10 C11 C12 119.8(9) .
C11 C12 C13 121.7(9) .
C8 C13 C12 118.4(8) .
C8 C13 N4 125.7(7) .
C12 C13 N4 115.2(7) .
O4 C14 N4 126.5(7) .
O4 C14 N5 122.1(7) .
N4 C14 N5 111.3(7) .
C16 C15 C20 120.8(8) .
C16 C15 N5 116.2(7) .
C20 C15 N5 122.8(7) .
C15 C16 C17 120.9(8) .
C18 C17 C16 119.3(8) .
C17 C18 C19 120.5(9) .
C18 C19 C20 121.1(8) .
C15 C20 N6 121.9(7) .
C15 C20 C19 117.3(7) .
N6 C20 C19 120.7(7) .
O5 C21 N7 122.9(6) .
O5 C21 N6 122.6(7) .
N7 C21 N6 114.3(7) .
N7 C22 C22 109.3(7) 3
N9 C23 C24 118.0(13) .
C23 C24 C25 109.6(16) .
C50 C25 C24 109.6(19) .
C52 C26 C51 105(3) .
C52 C26 C53 22(2) .
C51 C26 C53 116(3) .
C28 C27 N9 122(3) .
C27 C28 C29 117(4) .
C30 C29 C28 79(3) .
C33 C31 N9 112.1(14) .
C54 C32 C33 111.2(17) .
C31 C33 C32 112.5(16) .
C35 C34 N9 125.8(15) .
C34 C35 C36 118.5(19) .
C37 C36 C35 114(2) .
C39 C38 N8 112.6(10) .
C38 C39 C40 100.8(14) .
C41 C40 C39 108(6) .
N8 C42 C43 111.2(10) .
C42 C43 C44 103.5(14) .
C45 C44 C43 105.1(15) .
N8 C46 C47 112.5(8) .
C46 C47 C48 102.5(12) .
C49 C48 C47 121(3) .
C38 N8 C46 100.8(8) .
C38 N8 C42 114.3(11) .
C46 N8 C42 112.4(10) .
C38 N8 C51 115.8(10) .
C46 N8 C51 113.9(9) .
C42 N8 C51 100.3(9) .
C26 C51 N8 108.9(15) .
C53 C52 C26 118(9) .
C52 C53 C26 40(7) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 O1 1.165(17) .
N1 O2 1.197(18) .
N1 C1 1.623(16) .
N1A O1A 1.05(4) .
N1A C1 1.600(17) .
N2 C4 1.382(10) .
N2 C7 1.396(11) .
N3 C7 1.354(10) .
N3 C8 1.429(9) .
N4 C14 1.333(9) .
N4 C13 1.424(10) .
N5 C14 1.381(9) .
N5 C15 1.418(10) .
N6 C21 1.354(8) .
N6 C20 1.408(9) .
N7 C21 1.337(9) .
N7 C22 1.475(8) .
N9 C23 1.472(14) .
N9 C27 1.518(17) .
N9 C31 1.574(15) .
N9 C34 1.82(3) .
O3 C7 1.220(10) .
O4 C14 1.240(9) .
O5 C21 1.247(9) .
C1 C2 1.310(14) .
C1 C6 1.342(16) .
C2 C3 1.389(12) .
C3 C4 1.354(11) .
C4 C5 1.338(15) .
C5 C6 1.398(16) .
C8 C13 1.357(10) .
C8 C9 1.402(11) .
C9 C10 1.402(12) .
C10 C11 1.342(13) .
C11 C12 1.351(12) .
C12 C13 1.420(11) .
C15 C16 1.369(11) .
C15 C20 1.393(10) .
C16 C17 1.390(12) .
C17 C18 1.368(13) .
C18 C19 1.372(11) .
C19 C20 1.415(11) .
C22 C22 1.541(15) 3
C23 C24 1.534(16) .
C24 C25 1.571(18) .
C25 C50 1.54(2) .
C26 C52 1.31(9) .
C26 C51 1.35(3) .
C26 C53 1.78(5) .
C27 C28 1.27(3) .
C28 C29 1.85(5) .
C29 C30 1.31(3) .
C31 C33 1.518(18) .
C32 C54 1.521(19) .
C32 C33 1.560(19) .
C34 C35 1.44(3) .
C35 C36 1.52(3) .
C36 C37 1.41(3) .
C38 C39 1.510(17) .
C38 N8 1.511(13) .
C39 C40 1.79(3) .
C40 C41 0.79(4) .
C42 N8 1.530(16) .
C42 C43 1.61(2) .
C43 C44 1.62(2) .
C44 C45 1.44(3) .
C46 N8 1.513(12) .
C46 C47 1.554(16) .
C47 C48 1.60(2) .
C48 C49 1.03(3) .
N8 C51 1.530(16) .
C52 C53 0.74(6) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N5 H5 Br2 0.88 2.52 3.272(6) 144.4 1_554
N4 H4 Br2 0.88 2.63 3.342(6) 138.8 1_554
N2 H2 Br1 0.88 2.49 3.346(7) 164.4 .
N3 H3 Br1 0.88 3.20 3.924(6) 141.3 .
N6 H6 Br1 0.88 3.26 3.912(6) 133.0 .
N7 H7 Br1 0.88 2.55 3.350(6) 152.0 .
