#------------------------------------------------------------------------------
#$Date: 2010-01-30 15:59:17 +0200 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2013322.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_2013322
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2003
_journal_volume  59
_journal_page_first  o221
_journal_page_last  o224
_publ_section_title
;
Cone and 1,3-alternate conformers of
1,3-bis(ethoxycarbonylmethoxy)-2,4-dihydroxycalix[4]arene and
1,2,3,4-tetrakis(ethoxycarbonylmethoxy)calix[4]arene
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
loop_
_publ_author_name
  'Genorio, Bo\<stjan'
  'Kobe, Jo\<ze'
  'Giester, Gerald'
  'Leban, Ivan'
_chemical_name_common
;
2,4-Dihydroxy-1,3-bis(methoxycarbonylethoxy)calix[4]arene
;
_chemical_formula_moiety  'C36 H36 O8'
_chemical_formula_sum  'C36 H36 O8'
_chemical_formula_iupac  'C36 H36 O8'
_chemical_formula_weight  596.65
_chemical_melting_point  '170-172'
_symmetry_cell_setting  monoclinic
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y-1/2, z-1/2'
_cell_length_a  10.1364(5)
_cell_length_b  10.9403(5)
_cell_length_c  27.7309(10)
_cell_angle_alpha  90.00
_cell_angle_beta  97.917(3)
_cell_angle_gamma  90.00
_cell_volume  3045.9(2)
_cell_formula_units_Z  4
_cell_measurement_temperature  150(2)
_exptl_crystal_density_diffrn  1.301
_exptl_crystal_density_meas  '1.26(5)'
_diffrn_ambient_temperature  150(2)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
  O1 0.55518(11) 0.40004(12) 0.34327(4) 0.0357(3) Uani d . 1 . . O
  O2 0.47010(12) 0.48737(12) 0.42382(5) 0.0372(3) Uani d . 1 . . O
  H2 0.511(3) 0.451(2) 0.4020(9) 0.063(7) Uiso d . 1 . . H
  O3 0.40695(11) 0.74115(11) 0.39941(4) 0.0347(3) Uani d . 1 . . O
  O4 0.44742(12) 0.64100(13) 0.30877(5) 0.0416(3) Uani d . 1 . . O
  H4 0.443(2) 0.688(2) 0.3335(10) 0.062(7) Uiso d . 1 . . H
  O5 0.79333(14) 0.34387(17) 0.39910(5) 0.0592(4) Uani d . 1 . . O
  O6 0.90209(11) 0.42250(12) 0.34111(4) 0.0368(3) Uani d . 1 . . O
  O7 0.63881(15) 0.83154(14) 0.37722(5) 0.0556(4) Uani d . 1 . . O
  O8 0.65365(13) 0.96094(12) 0.44053(5) 0.0422(3) Uani d . 1 . . O
  C1 0.40375(17) 0.33973(16) 0.27145(6) 0.0342(4) Uani d . 1 . . C
  C2 0.30902(18) 0.25408(18) 0.25145(7) 0.0408(4) Uani d . 1 . . C
  H02 0.2736 0.2600 0.2180 0.049 Uiso calc R 1 . . H
  C3 0.2660(2) 0.16162(17) 0.27905(8) 0.0450(5) Uani d . 1 . . C
  H03 0.2021 0.1043 0.2645 0.054 Uiso calc R 1 . . H
  C4 0.3155(2) 0.15205(16) 0.32773(7) 0.0422(4) Uani d . 1 . . C
  H04 0.2822 0.0903 0.3469 0.051 Uiso calc R 1 . . H
  C5 0.41361(17) 0.23142(15) 0.34920(6) 0.0343(4) Uani d . 1 . . C
  C6 0.45835(16) 0.32205(15) 0.31998(6) 0.0311(4) Uani d . 1 . . C
  C7 0.46555(18) 0.22288(16) 0.40317(6) 0.0377(4) Uani d . 1 . . C
  H7A 0.4738 0.1356 0.4125 0.045 Uiso calc R 1 . . H
  H7B 0.5557 0.2594 0.4090 0.045 Uiso calc R 1 . . H
  C8 0.37756(17) 0.28644(16) 0.43553(6) 0.0322(4) Uani d . 1 . . C
  C9 0.28696(19) 0.22015(17) 0.45844(7) 0.0394(4) Uani d . 1 . . C
  H9 0.2790 0.1346 0.4529 0.047 Uiso calc R 1 . . H
  C10 0.20798(19) 0.27538(18) 0.48918(7) 0.0428(4) Uani d . 1 . . C
  H10 0.1469 0.2281 0.5045 0.051 Uiso calc R 1 . . H
  C11 0.21883(18) 0.39961(18) 0.49734(6) 0.0379(4) Uani d . 1 . . C
  H11 0.1662 0.4372 0.5190 0.045 Uiso calc R 1 . . H
  C12 0.30545(16) 0.47088(15) 0.47443(6) 0.0306(3) Uani d . 1 . . C
  C13 0.38489(16) 0.41310(15) 0.44379(5) 0.0293(3) Uani d . 1 . . C
  C14 0.31347(17) 0.60817(16) 0.48115(6) 0.0329(4) Uani d . 1 . . C
  H14A 0.4067 0.6353 0.4812 0.040 Uiso calc R 1 . . H
  H14B 0.2864 0.6300 0.5130 0.040 Uiso calc R 1 . . H
  C15 0.22394(17) 0.67361(15) 0.44086(6) 0.0315(4) Uani d . 1 . . C
  C16 0.08619(18) 0.67156(17) 0.44102(7) 0.0389(4) Uani d . 1 . . C
  H16 0.0515 0.6349 0.4677 0.047 Uiso calc R 1 . . H
  C17 -0.00094(19) 0.72144(19) 0.40346(8) 0.0446(5) Uani d . 1 . . C
  H17 -0.0941 0.7200 0.4047 0.054 Uiso calc R 1 . . H
  C18 0.04821(19) 0.77344(18) 0.36405(7) 0.0433(4) Uani d . 1 . . C
  H18 -0.0119 0.8060 0.3379 0.052 Uiso calc R 1 . . H
  C19 0.18502(18) 0.77865(15) 0.36226(7) 0.0355(4) Uani d . 1 . . C
  C20 0.27040(16) 0.73171(15) 0.40158(6) 0.0313(4) Uani d . 1 . . C
  C21 0.2363(2) 0.82373(16) 0.31651(7) 0.0422(4) Uani d . 1 . . C
  H21A 0.3296 0.8515 0.3248 0.051 Uiso calc R 1 . . H
  H22B 0.1822 0.8944 0.3031 0.051 Uiso calc R 1 . . H
  C22 0.22980(18) 0.72377(16) 0.27812(6) 0.0370(4) Uani d . 1 . . C
  C23 0.1161(2) 0.7133(2) 0.24378(7) 0.0470(5) Uani d . 1 . . C
  H23 0.0452 0.7697 0.2444 0.056 Uiso calc R 1 . . H
  C24 0.1048(2) 0.6219(2) 0.20871(7) 0.0503(5) Uani d . 1 . . C
  H24 0.0267 0.6158 0.1856 0.060 Uiso calc R 1 . . H
  C25 0.20793(19) 0.5397(2) 0.20771(6) 0.0437(5) Uani d . 1 . . C
  H25 0.2005 0.4779 0.1834 0.052 Uiso calc R 1 . . H
  C26 0.32230(17) 0.54583(17) 0.24158(6) 0.0356(4) Uani d . 1 . . C
  C27 0.33195(17) 0.63876(16) 0.27678(6) 0.0338(4) Uani d . 1 . . C
  C28 0.43074(18) 0.45075(18) 0.24121(6) 0.0376(4) Uani d . 1 . . C
  H28A 0.5177 0.4869 0.2545 0.045 Uiso calc R 1 . . H
  H28B 0.4355 0.4250 0.2073 0.045 Uiso calc R 1 . . H
  C29 0.67486(17) 0.4171(2) 0.32306(6) 0.0402(4) Uani d . 1 . . C
  H29A 0.6801 0.5028 0.3119 0.048 Uiso calc R 1 . . H
  H29B 0.6749 0.3631 0.2944 0.048 Uiso calc R 1 . . H
  C30 0.79399(17) 0.38900(17) 0.35979(6) 0.0343(4) Uani d . 1 . . C
  C31 1.03113(17) 0.39529(18) 0.36862(7) 0.0381(4) Uani d . 1 . . C
  H31A 1.0425 0.3060 0.3732 0.046 Uiso calc R 1 . . H
  H31B 1.0400 0.4348 0.4010 0.046 Uiso calc R 1 . . H
  C32 1.13250(17) 0.44482(18) 0.33940(7) 0.0402(4) Uani d . 1 . . C
  H32A 1.1272 0.4002 0.3086 0.060 Uiso calc R 1 . . H
  H32B 1.2217 0.4350 0.3577 0.060 Uiso calc R 1 . . H
  H32C 1.1151 0.5317 0.3328 0.060 Uiso calc R 1 . . H
  C33 0.4697(2) 0.8357(2) 0.43005(8) 0.0554(6) Uani d . 1 . . C
  H33A 0.4894 0.8057 0.4640 0.066 Uiso calc R 1 . . H
  H33B 0.4094 0.9069 0.4297 0.066 Uiso calc R 1 . . H
  C34 0.59667(18) 0.87292(16) 0.41183(6) 0.0362(4) Uani d . 1 . . C
  C35 0.7748(2) 1.01580(19) 0.42750(8) 0.0456(5) Uani d . 1 . . C
  H35A 0.7542 1.0680 0.3983 0.055 Uiso calc R 1 . . H
  H35B 0.8386 0.9517 0.4206 0.055 Uiso calc R 1 . . H
  C36 0.8322(3) 1.0911(2) 0.47067(10) 0.0661(7) Uani d . 1 . . C
  H36A 0.7647 1.1488 0.4789 0.099 Uiso calc R 1 . . H
  H36B 0.9097 1.1365 0.4627 0.099 Uiso calc R 1 . . H
  H36C 0.8595 1.0373 0.4985 0.099 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  O1 0.0243(6) 0.0507(7) 0.0340(6) -0.0048(5) 0.0108(5) -0.0072(5)
  O2 0.0408(7) 0.0351(6) 0.0396(7) -0.0030(5) 0.0189(6) -0.0007(5)
  O3 0.0292(6) 0.0341(6) 0.0413(6) -0.0055(5) 0.0066(5) -0.0028(5)
  O4 0.0317(7) 0.0536(8) 0.0380(7) -0.0013(6) -0.0001(5) -0.0067(6)
  O5 0.0406(8) 0.0958(12) 0.0423(8) -0.0021(8) 0.0096(6) 0.0218(8)
  O6 0.0240(6) 0.0506(7) 0.0359(6) -0.0040(5) 0.0048(5) 0.0036(5)
  O7 0.0561(9) 0.0648(10) 0.0489(8) -0.0217(7) 0.0173(7) -0.0163(7)
  O8 0.0384(7) 0.0377(7) 0.0501(7) -0.0084(5) 0.0052(6) -0.0046(6)
  C1 0.0296(8) 0.0400(9) 0.0351(9) 0.0013(7) 0.0114(7) -0.0085(7)
  C2 0.0377(10) 0.0459(10) 0.0397(9) 0.0000(8) 0.0079(8) -0.0139(8)
  C3 0.0440(11) 0.0369(10) 0.0549(12) -0.0060(8) 0.0096(9) -0.0156(9)
  C4 0.0474(11) 0.0283(9) 0.0535(11) -0.0021(8) 0.0159(9) -0.0065(8)
  C5 0.0330(9) 0.0295(8) 0.0422(9) 0.0080(7) 0.0116(7) -0.0041(7)
  C6 0.0246(8) 0.0345(9) 0.0359(8) 0.0014(6) 0.0102(6) -0.0077(7)
  C7 0.0392(10) 0.0318(9) 0.0428(10) 0.0090(7) 0.0086(8) 0.0047(7)
  C8 0.0331(9) 0.0336(9) 0.0295(8) 0.0047(7) 0.0031(7) 0.0055(7)
  C9 0.0446(10) 0.0318(9) 0.0421(10) -0.0011(8) 0.0076(8) 0.0076(7)
  C10 0.0429(10) 0.0448(10) 0.0434(10) -0.0061(8) 0.0149(8) 0.0097(8)
  C11 0.0374(9) 0.0463(10) 0.0321(9) 0.0004(8) 0.0125(7) 0.0034(7)
  C12 0.0313(8) 0.0368(9) 0.0235(7) -0.0005(7) 0.0030(6) 0.0009(6)
  C13 0.0279(8) 0.0348(8) 0.0250(7) -0.0003(6) 0.0034(6) 0.0042(6)
  C14 0.0359(9) 0.0374(9) 0.0263(8) -0.0008(7) 0.0068(7) -0.0043(7)
  C15 0.0324(9) 0.0296(8) 0.0334(8) -0.0011(7) 0.0075(7) -0.0085(7)
  C16 0.0338(9) 0.0419(10) 0.0433(10) 0.0001(8) 0.0136(8) -0.0068(8)
  C17 0.0293(9) 0.0485(11) 0.0571(12) 0.0053(8) 0.0097(8) -0.0069(9)
  C18 0.0369(10) 0.0397(10) 0.0515(11) 0.0095(8) 0.0000(8) -0.0013(8)
  C19 0.0366(9) 0.0256(8) 0.0441(10) 0.0016(7) 0.0051(7) -0.0003(7)
  C20 0.0287(8) 0.0264(8) 0.0390(9) -0.0015(6) 0.0054(7) -0.0044(7)
  C21 0.0466(11) 0.0296(9) 0.0492(11) 0.0003(8) 0.0028(8) 0.0119(8)
  C22 0.0400(10) 0.0366(9) 0.0340(9) -0.0028(8) 0.0038(7) 0.0143(7)
  C23 0.0430(11) 0.0518(12) 0.0442(10) 0.0045(9) -0.0010(8) 0.0183(9)
  C24 0.0452(11) 0.0650(13) 0.0367(10) -0.0021(10) -0.0086(8) 0.0109(9)
  C25 0.0433(10) 0.0579(12) 0.0284(8) -0.0072(9) 0.0000(8) 0.0049(8)
  C26 0.0339(9) 0.0469(10) 0.0264(8) -0.0075(8) 0.0060(7) 0.0070(7)
  C27 0.0324(9) 0.0400(9) 0.0290(8) -0.0067(7) 0.0042(7) 0.0086(7)
  C28 0.0332(9) 0.0541(11) 0.0269(8) -0.0049(8) 0.0096(7) -0.0034(7)
  C29 0.0257(8) 0.0611(12) 0.0355(9) -0.0032(8) 0.0103(7) 0.0007(8)
  C30 0.0297(8) 0.0401(9) 0.0342(9) -0.0027(7) 0.0083(7) -0.0035(7)
  C31 0.0276(9) 0.0448(10) 0.0401(9) -0.0011(7) -0.0016(7) 0.0005(8)
  C32 0.0261(8) 0.0454(10) 0.0491(10) -0.0013(8) 0.0048(7) -0.0036(8)
  C33 0.0496(12) 0.0644(14) 0.0537(12) -0.0244(10) 0.0125(10) -0.0199(11)
  C34 0.0392(10) 0.0353(9) 0.0325(8) -0.0012(7) -0.0007(7) 0.0022(7)
  C35 0.0409(10) 0.0445(11) 0.0526(11) -0.0096(8) 0.0104(9) -0.0034(9)
  C36 0.0653(15) 0.0475(12) 0.0786(16) -0.0220(11) -0.0146(13) -0.0051(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  O1 C6 . 1.391(2) ?
  O1 C29 . 1.4171(19) ?
  O2 C13 . 1.3582(19) ?
  O2 H2 . 0.88(3) ?
  O3 C20 . 1.398(2) ?
  O3 C33 . 1.431(2) ?
  O4 C27 . 1.368(2) ?
  O4 H4 . 0.86(3) ?
  O5 C30 . 1.198(2) ?
  O6 C30 . 1.326(2) ?
  O6 C31 . 1.451(2) ?
  O7 C34 . 1.192(2) ?
  O8 C34 . 1.330(2) ?
  O8 C35 . 1.457(2) ?
  C1 C6 . 1.396(2) ?
  C1 C2 . 1.400(3) ?
  C1 C28 . 1.522(3) ?
  C2 C3 . 1.375(3) ?
  C2 H02 . 0.9500 ?
  C3 C4 . 1.378(3) ?
  C3 H03 . 0.9500 ?
  C4 C5 . 1.391(3) ?
  C4 H04 . 0.9500 ?
  C5 C6 . 1.395(2) ?
  C5 C7 . 1.520(3) ?
  C7 C8 . 1.518(2) ?
  C7 H7A . 0.9900 ?
  C7 H7B . 0.9900 ?
  C8 C9 . 1.391(2) ?
  C8 C13 . 1.405(2) ?
  C9 C10 . 1.386(3) ?
  C9 H9 . 0.9500 ?
  C10 C11 . 1.380(3) ?
  C10 H10 . 0.9500 ?
  C11 C12 . 1.391(2) ?
  C11 H11 . 0.9500 ?
  C12 C13 . 1.400(2) ?
  C12 C14 . 1.514(2) ?
  C14 C15 . 1.518(2) ?
  C14 H14A . 0.9900 ?
  C14 H14B . 0.9900 ?
  C15 C16 . 1.397(2) ?
  C15 C20 . 1.398(2) ?
  C16 C17 . 1.382(3) ?
  C16 H16 . 0.9500 ?
  C17 C18 . 1.384(3) ?
  C17 H17 . 0.9500 ?
  C18 C19 . 1.396(3) ?
  C18 H18 . 0.9500 ?
  C19 C20 . 1.393(2) ?
  C19 C21 . 1.518(3) ?
  C21 C22 . 1.521(3) ?
  C21 H21A . 0.9900 ?
  C21 H22B . 0.9900 ?
  C22 C23 . 1.395(3) ?
  C22 C27 . 1.396(3) ?
  C23 C24 . 1.389(3) ?
  C23 H23 . 0.9500 ?
  C24 C25 . 1.382(3) ?
  C24 H24 . 0.9500 ?
  C25 C26 . 1.390(2) ?
  C25 H25 . 0.9500 ?
  C26 C27 . 1.404(3) ?
  C26 C28 . 1.514(3) ?
  C28 H28A . 0.9900 ?
  C28 H28B . 0.9900 ?
  C29 C30 . 1.500(2) ?
  C29 H29A . 0.9900 ?
  C29 H29B . 0.9900 ?
  C31 C32 . 1.495(3) ?
  C31 H31A . 0.9900 ?
  C31 H31B . 0.9900 ?
  C32 H32A . 0.9800 ?
  C32 H32B . 0.9800 ?
  C32 H32C . 0.9800 ?
  C33 C34 . 1.502(3) ?
  C33 H33A . 0.9900 ?
  C33 H33B . 0.9900 ?
  C35 C36 . 1.503(3) ?
  C35 H35A . 0.9900 ?
  C35 H35B . 0.9900 ?
  C36 H36A . 0.9800 ?
  C36 H36B . 0.9800 ?
  C36 H36C . 0.9800 ?
_cod_database_code 2013322