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#$Date: 2016-02-13 21:28:24 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176429 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/09/4100943.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_4100943
loop_
_publ_author_name
'Isaacs, Lyle'
'Park, Sang-Kyu'
'Liu, Simin'
'Ko, Young Ho'
'Selvapalam, Narayanan'
'Kim, Youngkook'
'Kim, Hyunuk'
'Zavalij, Peter Y.'
'Kim, Ghyung-Hwa'
'Lee, Heung-Soo'
'Kim, Kimoon'
_publ_section_title
;
The Inverted Cucurbit[n]uril Family
;
_journal_issue                   51
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18000
_journal_page_last               18001
_journal_paper_doi               10.1021/ja056988k
_journal_volume                  127
_journal_year                    2005
_chemical_formula_moiety         'C36 H36 N24 O12, H3 O, 8.7(H2 O), Cl'
_chemical_formula_sum            'C36 H56.4 Cl N24 O21.7'
_chemical_formula_weight         1208.10
_chemical_name_common            inv-CB6
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 104.923(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.434(2)
_cell_length_b                   16.122(3)
_cell_length_c                   12.667(2)
_cell_measurement_temperature    213(2)
_cell_volume                     2453.6(8)
_diffrn_ambient_temperature      213(2)
_exptl_crystal_density_diffrn    1.635
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C36 H56.40 Cl N24 O21.70'
_cod_database_code               4100943
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
O12 O 0.5637(2) 0.6625(2) 0.2179(2) 0.0367(7) Uani 1 1 d . . .
O13 O 0.2502(3) 0.90717(18) 0.3463(2) 0.0375(8) Uani 1 1 d . . .
N11 N 0.3757(3) 0.6874(2) 0.1937(3) 0.0305(8) Uani 1 1 d . . .
N12 N 0.2523(3) 0.7894(2) 0.2444(3) 0.0369(9) Uani 1 1 d . . .
N13 N 0.4894(3) 0.6996(2) 0.3596(3) 0.0285(8) Uani 1 1 d . . .
N14 N 0.3556(3) 0.7928(2) 0.4147(3) 0.0316(8) Uani 1 1 d . . .
C11 C 0.3006(3) 0.7064(3) 0.2611(3) 0.0289(10) Uani 1 1 d . . .
H11 H 0.2427 0.6632 0.2550 0.008(8) Uiso 1 1 calc R . .
C12 C 0.4830(3) 0.6819(3) 0.2523(3) 0.0281(9) Uani 1 1 d . . .
C13 C 0.2839(3) 0.8367(3) 0.3355(3) 0.0273(10) Uani 1 1 d . . .
C14 C 0.3788(3) 0.7106(3) 0.3781(3) 0.0271(9) Uani 1 1 d . . .
H14 H 0.3616 0.6665 0.4255 0.022(10) Uiso 1 1 calc R . .
C15 C 0.5907(3) 0.6911(3) 0.4463(3) 0.0290(10) Uani 1 1 d . . .
H15A H 0.6394 0.6503 0.4246 0.033(12) Uiso 1 1 calc R . .
H15B H 0.6300 0.7443 0.4576 0.013(9) Uiso 1 1 calc R . .
C16 C 0.4199(3) 0.8290(2) 0.5159(3) 0.0268(10) Uani 1 1 d . . .
H16A H 0.3769 0.8735 0.5383 0.032(11) Uiso 1 1 calc R . .
H16B H 0.4884 0.8532 0.5046 0.016(9) Uiso 1 1 calc R . .
O22 O 0.5555(3) 0.52444(18) 0.5133(2) 0.0356(7) Uani 1 1 d . . .
O23 O 0.2965(2) 0.78776(19) 0.6703(2) 0.0340(7) Uani 1 1 d . . .
N21 N 0.5679(3) 0.6651(2) 0.5469(3) 0.0270(8) Uani 1 1 d . . .
N22 N 0.4478(3) 0.7669(2) 0.6011(3) 0.0253(8) Uani 1 1 d . . .
N23 N 0.5348(3) 0.5820(2) 0.6745(3) 0.0280(8) Uani 1 1 d . . .
N24 N 0.4317(3) 0.6906(2) 0.7407(3) 0.0279(8) Uani 1 1 d . . .
C21 C 0.5522(3) 0.7222(2) 0.6299(3) 0.0246(9) Uani 1 1 d . . .
H21 H 0.6166 0.7599 0.6549 0.017(10) Uiso 1 1 calc R . .
C22 C 0.5524(3) 0.5843(3) 0.5726(3) 0.0261(9) Uani 1 1 d . . .
C23 C 0.3814(3) 0.7521(2) 0.6706(3) 0.0238(9) Uani 1 1 d . . .
C24 C 0.5373(3) 0.6636(2) 0.7230(3) 0.0252(9) Uani 1 1 d . . .
H24 H 0.5991 0.6693 0.7898 0.020(10) Uiso 1 1 calc R . .
C25 C 0.5274(3) 0.5065(2) 0.7333(3) 0.0274(9) Uani 1 1 d . . .
H25A H 0.5597 0.4611 0.7002 0.026(11) Uiso 1 1 calc R . .
H25B H 0.5721 0.5128 0.8088 0.042(13) Uiso 1 1 calc R . .
C26 C 0.3892(3) 0.6650(3) 0.8315(3) 0.0274(9) Uani 1 1 d . . .
H26A H 0.3453 0.7107 0.8501 0.029(11) Uiso 1 1 calc R . .
H26B H 0.4523 0.6554 0.8948 0.026(11) Uiso 1 1 calc R . .
O32 O 0.3940(3) 0.3818(2) 0.6030(3) 0.0476(9) Uani 1 1 d . . .
O33 O 0.1480(2) 0.65479(18) 0.7712(2) 0.0358(7) Uani 1 1 d . . .
N31 N 0.4155(3) 0.4843(2) 0.7345(3) 0.0283(8) Uani 1 1 d . . .
N32 N 0.3205(3) 0.5910(2) 0.8126(3) 0.0284(8) Uani 1 1 d . . .
N33 N 0.2687(3) 0.4004(2) 0.7067(3) 0.0282(8) Uani 1 1 d . . .
N34 N 0.1675(3) 0.5134(2) 0.7654(3) 0.0291(8) Uani 1 1 d . . .
C31 C 0.3631(3) 0.5072(2) 0.8210(3) 0.0259(9) Uani 1 1 d . . .
H31 H 0.4125 0.4959 0.8944 0.008(8) Uiso 1 1 calc R . .
C32 C 0.3632(4) 0.4181(3) 0.6745(4) 0.0305(10) Uani 1 1 d . . .
C33 C 0.2059(3) 0.5932(3) 0.7806(3) 0.0254(9) Uani 1 1 d . . .
C34 C 0.2568(3) 0.4525(3) 0.7971(3) 0.0282(10) Uani 1 1 d . . .
H34 H 0.2515 0.4195 0.8614 0.035(12) Uiso 1 1 calc R . .
C35 C 0.2004(3) 0.3290(2) 0.6687(3) 0.0277(10) Uani 1 1 d . . .
H35A H 0.2455 0.2870 0.6441 0.038(12) Uiso 1 1 calc R . .
H35B H 0.1758 0.3054 0.7298 0.037(12) Uiso 1 1 calc R . .
C36 C 0.0507(3) 0.4929(3) 0.7393(3) 0.0302(10) Uani 1 1 d . . .
H36A H 0.0093 0.5419 0.7523 0.09(2) Uiso 1 1 calc R . .
H36B H 0.0394 0.4493 0.7892 0.046(14) Uiso 1 1 calc R . .
O42 O 0.1735(2) 0.3015(2) 0.4378(2) 0.0376(7) Uani 1 1 d . . .
O43 O -0.0935(3) 0.58516(19) 0.5647(2) 0.0398(8) Uani 1 1 d . . .
N41 N 0.1042(3) 0.3469(2) 0.5808(3) 0.0289(8) Uani 1 1 d . . .
N42 N 0.0048(3) 0.4653(2) 0.6286(3) 0.0294(8) Uani 1 1 d . . .
N43 N -0.0051(3) 0.3529(2) 0.4122(3) 0.0268(8) Uani 1 1 d . . .
N44 N -0.1150(3) 0.4633(2) 0.4651(3) 0.0286(8) Uani 1 1 d . . .
C41 C 0.0010(3) 0.3778(3) 0.5968(3) 0.0257(9) Uani 1 1 d . . .
H41 H -0.0277 0.3422 0.6472 0.024(10) Uiso 1 1 calc R . .
C42 C 0.0986(3) 0.3311(2) 0.4734(3) 0.0277(10) Uani 1 1 d . . .
C43 C -0.0706(3) 0.5120(3) 0.5534(3) 0.0277(9) Uani 1 1 d . . .
C44 C -0.0778(3) 0.3785(3) 0.4807(3) 0.0262(9) Uani 1 1 d . . .
H44 H -0.1409 0.3396 0.4742 0.010(9) Uiso 1 1 calc R . .
C45 C -0.0491(3) 0.3221(2) 0.3011(3) 0.0269(9) Uani 1 1 d . . .
H45A H 0.0019 0.2800 0.2859 0.024(11) Uiso 1 1 calc R . .
H45B H -0.1209 0.2952 0.2959 0.033(11) Uiso 1 1 calc R . .
C46 C -0.1993(4) 0.4923(3) 0.3711(3) 0.0336(10) Uani 1 1 d . . .
H46A H -0.2298 0.5447 0.3900 0.029(11) Uiso 1 1 calc R . .
H46B H -0.2602 0.4518 0.3541 0.027(11) Uiso 1 1 calc R . .
O52 O 0.0895(3) 0.3566(2) 0.1549(3) 0.0410(8) Uani 1 1 d . . .
O53 O -0.1508(3) 0.64844(18) 0.2837(3) 0.0411(8) Uani 1 1 d . . .
N51 N -0.0639(3) 0.3864(2) 0.2191(3) 0.0280(8) Uani 1 1 d . . .
N52 N -0.1594(3) 0.5052(2) 0.2742(3) 0.0284(8) Uani 1 1 d . . .
N53 N -0.0386(3) 0.4578(2) 0.0792(3) 0.0298(8) Uani 1 1 d . . .
N54 N -0.1339(3) 0.5763(2) 0.1318(3) 0.0287(8) Uani 1 1 d . . .
C51 C -0.1592(3) 0.4417(2) 0.1940(3) 0.0256(9) Uani 1 1 d . . .
H51 H -0.2301 0.4105 0.1752 0.030(11) Uiso 1 1 calc R . .
C52 C 0.0055(3) 0.3972(3) 0.1527(3) 0.0288(10) Uani 1 1 d . . .
C53 C -0.1478(3) 0.5834(3) 0.2352(3) 0.0296(10) Uani 1 1 d . . .
C54 C -0.1420(3) 0.4912(2) 0.0943(3) 0.0273(9) Uani 1 1 d . . .
H54 H -0.2046 0.4832 0.0287 0.014(9) Uiso 1 1 calc R . .
C55 C 0.0110(4) 0.4843(3) -0.0067(3) 0.0290(10) Uani 1 1 d . . .
H55A H -0.0482 0.4912 -0.0741 0.019(10) Uiso 1 1 calc R . .
H55B H 0.0606 0.4404 -0.0194 0.019(10) Uiso 1 1 calc R . .
C56 C -0.1443(3) 0.6471(3) 0.0593(4) 0.0299(10) Uani 1 1 d . . .
H56A H -0.1893 0.6310 -0.0133 0.039(13) Uiso 1 1 calc R . .
H56B H -0.1841 0.6914 0.0864 0.045(14) Uiso 1 1 calc R . .
O62 O 0.2488(3) 0.50149(19) 0.0703(3) 0.0401(8) Uani 1 1 d . . .
O63 O -0.0305(3) 0.79277(19) 0.1631(3) 0.0390(8) Uani 1 1 d . . .
N61 N 0.0740(3) 0.5613(2) 0.0155(3) 0.0285(8) Uani 1 1 d . . .
N62 N -0.0393(3) 0.6788(2) 0.0493(3) 0.0309(8) Uani 1 1 d . . .
N63 N 0.2235(3) 0.6428(2) 0.0483(3) 0.0297(8) Uani 1 1 d . . .
N64 N 0.1105(3) 0.7603(2) 0.0820(3) 0.0264(8) Uani 1 1 d . . .
C61 C 0.0280(3) 0.6434(2) -0.0175(3) 0.0257(9) Uani 1 1 d . . .
H61 H -0.0122 0.6444 -0.0958 0.026(11) Uiso 1 1 calc R . .
C62 C 0.1878(3) 0.5615(3) 0.0483(3) 0.0291(10) Uani 1 1 d . . .
C63 C 0.0099(4) 0.7472(3) 0.1054(3) 0.0291(10) Uani 1 1 d . . .
C64 C 0.1328(3) 0.6997(3) 0.0054(3) 0.0263(9) Uani 1 1 d . . .
H64 H 0.1408 0.7268 -0.0624 0.064(17) Uiso 1 1 calc R . .
C65 C 0.3383(3) 0.6653(3) 0.0779(3) 0.0309(10) Uani 1 1 d . . .
H65A H 0.3498 0.7126 0.0334 0.018(10) Uiso 1 1 calc R . .
H65B H 0.3829 0.6188 0.0628 0.052(15) Uiso 1 1 calc R . .
C66 C 0.1887(4) 0.8203(3) 0.1391(3) 0.0315(10) Uani 1 1 d . . .
H66A H 0.1489 0.8707 0.1500 0.045(13) Uiso 1 1 calc R . .
H66B H 0.2398 0.8349 0.0947 0.027(11) Uiso 1 1 calc R . .
Cl1 Cl 0.40956(10) 0.87919(8) 0.99120(11) 0.0508(3) Uani 1 1 d . . .
O1W O 0.2091(3) 0.0350(2) 0.1919(3) 0.0467(9) Uani 1 1 d D . .
H11W H 0.206(4) -0.005(2) 0.247(3) 0.056 Uiso 1 1 d D . .
H12W H 0.193(4) 0.0892(15) 0.215(4) 0.056 Uiso 1 1 d D . .
O2W O 0.2911(3) 0.3073(2) 0.1071(3) 0.0546(9) Uani 1 1 d D . .
H21W H 0.302(4) 0.294(3) 0.037(2) 0.066 Uiso 1 1 d D . .
H22W H 0.359(2) 0.333(3) 0.148(3) 0.066 Uiso 1 1 d D . .
H23W H 0.230(3) 0.346(2) 0.093(4) 0.066 Uiso 1 1 d D . .
O3W O 0.4726(3) 0.3893(2) 0.1989(3) 0.0609(10) Uani 1 1 d D . .
H31W H 0.442(4) 0.417(3) 0.253(4) 0.073 Uiso 1 1 d D . .
H32W H 0.517(4) 0.432(3) 0.177(4) 0.073 Uiso 1 1 d D . .
O4W O 0.4284(3) 0.5014(2) 0.3135(3) 0.0595(10) Uani 1 1 d D . .
H41W H 0.466(4) 0.499(3) 0.3908(17) 0.071 Uiso 1 1 d D . .
H42W H 0.473(4) 0.541(3) 0.286(4) 0.071 Uiso 1 1 d D . .
O5W O 0.5962(3) 0.5759(2) 0.0303(3) 0.0582(10) Uani 1 1 d D . .
H51W H 0.570(4) 0.592(3) 0.093(3) 0.070 Uiso 1 1 d D . .
H52W H 0.598(5) 0.5162(11) 0.035(4) 0.070 Uiso 1 1 d D . .
O6W O 0.3651(3) 0.2840(2) 0.9216(3) 0.0550(10) Uani 1 1 d D . .
H61W H 0.441(2) 0.302(3) 0.954(4) 0.066 Uiso 1 1 d D . .
H62W H 0.376(4) 0.250(3) 0.862(3) 0.066 Uiso 1 1 d D . .
O7W O 0.1813(4) 0.1922(3) 0.2614(3) 0.0667(11) Uani 1 1 d D . .
H71W H 0.154(5) 0.172(3) 0.322(4) 0.080 Uiso 1 1 d D . .
H72W H 0.165(5) 0.2506(13) 0.258(5) 0.080 Uiso 1 1 d D . .
O8W O 0.0466(4) 0.6804(3) 0.4684(4) 0.0809(14) Uani 1 1 d D . .
H81W H -0.013(4) 0.657(4) 0.495(5) 0.097 Uiso 1 1 d D . .
H82W H 0.045(5) 0.658(4) 0.397(3) 0.097 Uiso 1 1 d D . .
O9W O 0.2411(5) 0.4681(6) 0.3505(6) 0.143(4) Uani 0.966(15) 1 d PD . .
H91W H 0.252(8) 0.413(3) 0.326(9) 0.171 Uiso 0.966(15) 1 d PD . .
H92W H 0.316(3) 0.490(5) 0.365(8) 0.171 Uiso 0.966(15) 1 d PD . .
O10W O 0.2389(6) 0.5836(4) 0.5088(5) 0.086(3) Uani 0.748(12) 1 d PD . .
H101 H 0.200(6) 0.573(6) 0.433(3) 0.103 Uiso 0.748(12) 1 d PD . .
H102 H 0.182(5) 0.613(5) 0.535(6) 0.103 Uiso 0.748(12) 1 d PD . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O12 C12 1.233(5) . ?
O13 C13 1.231(5) . ?
N11 C12 1.352(5) . ?
N11 C11 1.452(5) . ?
N11 C65 1.464(5) . ?
N12 C13 1.354(5) . ?
N12 C66 1.452(5) . ?
N12 C11 1.460(6) . ?
N13 C12 1.371(5) . ?
N13 C15 1.449(5) . ?
N13 C14 1.463(5) . ?
N14 C13 1.357(5) . ?
N14 C16 1.447(5) . ?
N14 C14 1.458(5) . ?
C11 C14 1.550(6) . ?
C11 H11 0.9900 . ?
C14 H14 0.9900 . ?
C15 N21 1.438(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C16 N22 1.448(5) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
O22 C22 1.230(5) . ?
O23 C23 1.202(5) . ?
N21 C22 1.367(5) . ?
N21 C21 1.447(5) . ?
N22 C23 1.374(5) . ?
N22 C21 1.448(5) . ?
N23 C22 1.364(5) . ?
N23 C25 1.442(5) . ?
N23 C24 1.448(5) . ?
N24 C23 1.369(5) . ?
N24 C26 1.443(5) . ?
N24 C24 1.455(5) . ?
C21 C24 1.559(6) . ?
C21 H21 0.9900 . ?
C24 H24 0.9900 . ?
C25 N31 1.440(5) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C26 N32 1.451(5) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
O32 C32 1.220(5) . ?
O33 C33 1.214(5) . ?
N31 C32 1.373(5) . ?
N31 C31 1.460(5) . ?
N32 C33 1.378(5) . ?
N32 C31 1.444(5) . ?
N33 C32 1.369(5) . ?
N33 C35 1.439(5) . ?
N33 C34 1.457(5) . ?
N34 C33 1.369(5) . ?
N34 C36 1.442(5) . ?
N34 C34 1.459(5) . ?
C31 C34 1.552(6) . ?
C31 H31 0.9900 . ?
C34 H34 0.9900 . ?
C35 N41 1.438(5) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C36 N42 1.442(5) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
O42 C42 1.231(5) . ?
O43 C43 1.230(5) . ?
N41 C42 1.367(5) . ?
N41 C41 1.439(5) . ?
N42 C43 1.376(5) . ?
N42 C41 1.464(5) . ?
N43 C42 1.368(5) . ?
N43 C45 1.460(5) . ?
N43 C44 1.465(5) . ?
N44 C43 1.361(5) . ?
N44 C44 1.441(5) . ?
N44 C46 1.447(5) . ?
C41 C44 1.543(6) . ?
C41 H41 0.9900 . ?
C44 H44 0.9900 . ?
C45 N51 1.446(5) . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C46 N52 1.453(5) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
O52 C52 1.227(5) . ?
O53 C53 1.221(5) . ?
N51 C52 1.363(5) . ?
N51 C51 1.452(5) . ?
N52 C53 1.376(6) . ?
N52 C51 1.442(5) . ?
N53 C52 1.363(5) . ?
N53 C55 1.447(5) . ?
N53 C54 1.452(5) . ?
N54 C53 1.370(5) . ?
N54 C54 1.447(5) . ?
N54 C56 1.449(5) . ?
C51 C54 1.553(6) . ?
C51 H51 0.9900 . ?
C54 H54 0.9900 . ?
C55 N61 1.455(5) . ?
C55 H55A 0.9800 . ?
C55 H55B 0.9800 . ?
C56 N62 1.438(5) . ?
C56 H56A 0.9800 . ?
C56 H56B 0.9800 . ?
O62 C62 1.217(5) . ?
O63 C63 1.231(5) . ?
N61 C62 1.368(5) . ?
N61 C61 1.460(5) . ?
N62 C63 1.367(5) . ?
N62 C61 1.451(5) . ?
N63 C62 1.383(5) . ?
N63 C65 1.426(5) . ?
N63 C64 1.447(5) . ?
N64 C63 1.374(5) . ?
N64 C66 1.429(5) . ?
N64 C64 1.453(5) . ?
C61 C64 1.553(6) . ?
C61 H61 0.9900 . ?
C64 H64 0.9900 . ?
C65 H65A 0.9800 . ?
C65 H65B 0.9800 . ?
C66 H66A 0.9800 . ?
C66 H66B 0.9800 . ?
O1W H11W 0.959(17) . ?
O1W H12W 0.959(17) . ?
O2W H21W 0.964(17) . ?
O2W H22W 0.966(17) . ?
O2W H23W 0.966(17) . ?
O3W H31W 0.971(17) . ?
O3W H32W 0.968(17) . ?
O4W H41W 0.971(17) . ?
O4W H42W 0.972(17) . ?
O5W H51W 0.967(17) . ?
O5W H52W 0.965(17) . ?
O6W H61W 0.970(17) . ?
O6W H62W 0.969(17) . ?
O7W H71W 0.962(17) . ?
O7W H72W 0.961(17) . ?
O8W H81W 0.961(17) . ?
O8W H82W 0.966(17) . ?
O9W H91W 0.969(17) . ?
O9W H92W 0.972(17) . ?
O10W H101 0.974(17) . ?
O10W H102 0.969(17) . ?
