#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/70/4117093.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_4117093
loop_
_publ_author_name
'Kazuhisa Hiratani'
'Kazuyuki Kasuga'
'Midori Goto'
'Hirotaka Uzawa'
_publ_section_title
;
 Tandem Claisen Rearrangement: A Novel, One-Step Synthesis of Calixarene
 Analogues from Macrocyclic Polyethers
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12677
_journal_page_last               12678
_journal_paper_doi               10.1021/ja9722887
_journal_volume                  119
_journal_year                    1997
_chemical_compound_source        synthesis
_chemical_formula_moiety         ' C54 O12 H64 '
_chemical_formula_sum            'C54 H64 O12'
_chemical_formula_weight         905.09
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_type_scat_source           'International Tables (1974)'
_cell_angle_alpha                109.31(1)
_cell_angle_beta                 96.70(1)
_cell_angle_gamma                116.34(1)
_cell_formula_units_Z            1
_cell_length_a                   11.018(2)
_cell_length_b                   11.137(2)
_cell_length_c                   12.817(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    23
_cell_measurement_theta_max      30
_cell_measurement_theta_min      20
_cell_volume                     1264.0(4)
_computing_cell_refinement       Crystan-GM
_computing_data_collection       Crystan-GM
_computing_data_reduction        Crystan-GM
_computing_molecular_graphics    Crystan-GM
_computing_publication_material  Crystan-GM
_computing_structure_refinement  Crystan-GM
_computing_structure_solution    Crystan-GM
_diffrn_measurement_device       'Mac Science MXC18'
_diffrn_measurement_method       theta/omega
_diffrn_radiation_type           ' Mo K\a '
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.03
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6187
_diffrn_reflns_theta_max         25
_exptl_absorpt_coefficient_mu    0.08
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            nocolour
_exptl_crystal_density_diffrn    1.19
_exptl_crystal_description       prizm
_exptl_crystal_size_max          0.400000
_exptl_crystal_size_mid          0.200000
_exptl_crystal_size_min          0.200000
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.28
_refine_ls_extinction_coef       0.0000
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   0.12510E+01
_refine_ls_hydrogen_treatment    D-Fourier
_refine_ls_number_reflns         2852
_refine_ls_R_factor_obs          0.0613
_refine_ls_shift/esd_max         0.4695
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      ' Count statistics    '
_refine_ls_wR_factor_obs         0.1025
_reflns_number_observed          5010
_reflns_number_total             5706
_reflns_observed_criterion       refl_observed_if_F_>_3.00_sigma(F)
_cod_data_source_file            ja9722887_2.cif
_cod_data_source_block           goto4a_2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value ' triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value ' none ' changed
to 'none' according to the built-in table from CIF Core dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1264(1)
_cod_original_sg_symbol_H-M      ' P -1'
_cod_original_formula_sum        ' C54 O12 H64 '
_cod_database_code               4117093
loop_
_symmetry_equiv_pos_as_xyz
' +x, +y,  +z'
' -x, -y,  -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_thermal_displace_type
C(1) 0.6117(5) -0.2811(4) 0.1789(3) 0.074 1.000 Uij
C(2) 0.6159(3) -0.2946(3) 0.2928(3) 0.066 1.000 Uij
C(3) 0.7463(4) -0.2366(3) 0.3747(3) 0.068 1.000 Uij
C(4) 0.7559(3) -0.2308(3) 0.4847(3) 0.066 1.000 Uij
C(5) 0.6308(3) -0.2834(3) 0.5139(3) 0.062 1.000 Uij
C(6) 0.4977(3) -0.3452(3) 0.4360(2) 0.054 1.000 Uij
C(7) 0.4922(3) -0.3524(3) 0.3243(3) 0.056 1.000 Uij
C(8) 0.3636(3) -0.4001(3) 0.4698(3) 0.057 1.000 Uij
C(9) 0.3834(3) -0.3049(3) 0.5934(3) 0.057 1.000 Uij
C(10) 0.3928(3) -0.3494(3) 0.6817(3) 0.066 1.000 Uij
C(11) 0.4171(4) -0.2599(4) 0.7962(3) 0.073 1.000 Uij
C(12) 0.4369(4) -0.1201(4) 0.8207(3) 0.070 1.000 Uij
C(13) 0.4303(3) -0.0682(3) 0.7360(3) 0.060 1.000 Uij
C(14) 0.3986(3) -0.1648(3) 0.6215(3) 0.056 1.000 Uij
C(15) 0.4670(3) 0.0916(3) 0.7720(3) 0.060 1.000 Uij
C(16) 0.3543(3) 0.1250(3) 0.8019(3) 0.065 1.000 Uij
C(17) 0.2347(5) 0.0316(5) 0.8098(4) 0.097 1.000 Uij
C(18) 0.2849(5) -0.5622(5) 0.1782(4) 0.084 1.000 Uij
C(19) 0.1773(5) -0.6016(6) 0.0720(4) 0.104 1.000 Uij
C(20) -0.0398(9) -0.7962(11) -0.0758(7) 0.168 1.000 Uij
C(21) -0.1545(11) -0.9375(20) -0.0974(10) 0.230 1.000 Uij
C(22) 0.8973(4) -0.1661(5) 0.5719(4) 0.092 1.000 Uij
C(23) 0.2988(4) -0.0768(4) 0.5070(3) 0.074 1.000 Uij
C(24) 0.1653(4) -0.1920(4) 0.4099(3) 0.086 1.000 Uij
C(25) -0.0117(7) -0.4471(6) 0.3025(12) 0.173 1.000 Uij
C(26) -0.0401(8) -0.5829(7) 0.2987(13) 0.183 1.000 Uij
C(27) 0.4204(6) -0.3133(5) 0.8898(3) 0.116 1.000 Uij
O(1) 0.3624(2) -0.4075(2) 0.2441(2) 0.068 1.000 Uij
O(2) 0.1861(6) -0.5207(6) 0.0288(4) 0.201 1.000 Uij
O(3) 0.0720(4) -0.7403(4) 0.0309(3) 0.117 1.000 Uij
O(4) 0.3960(2) -0.1231(2) 0.5311(2) 0.065 1.000 Uij
O(5) 0.1023(5) -0.1636(4) 0.3487(3) 0.152 1.000 Uij
O(6) 0.1167(3) -0.3261(3) 0.4019(3) 0.107 1.000 Uij
H(1A) 0.519(4) -0.354(4) 0.122(3) 0.050 1.000 Uiso
H(1B) 0.672(4) -0.300(5) 0.149(4) 0.07 1.000 Uiso
H(3) 0.829(5) -0.202(5) 0.358(3) 0.07 1.000 Uiso
H(5) 0.636(5) -0.274(5) 0.593(4) 0.08 1.000 Uiso
H(8A) 0.294(4) -0.393(4) 0.423(3) 0.045 1.000 Uiso
H(8B) 0.331(4) -0.495(4) 0.457(3) 0.050 1.000 Uiso
H(10) 0.387(3) -0.444(4) 0.664(3) 0.050 1.000 Uiso
H(12) 0.453(4) -0.059(4) 0.896(3) 0.06 1.000 Uiso
H(15A) 0.558(4) 0.154(4) 0.843(3) 0.051 1.000 Uiso
H(15B) 0.485(3) 0.110(3) 0.708(3) 0.042 1.000 Uiso
H(17A) 0.166(4) 0.062(5) 0.827(3) 0.07 1.000 Uiso
H(17B) 0.196(5) -0.078(5) 0.783(4) 0.08 1.000 Uiso
H(18A) 0.245(6) -0.613(7) 0.218(5) 0.11 1.000 Uiso
H(18B) 0.342(7) -0.607(8) 0.156(5) 0.13 1.000 Uiso
H(21A) -0.22601 -0.97164 -0.16779 0.16 1.000 Uiso
H(21B) -0.19271 -0.93114 -0.03349 0.25 1.000 Uiso
H(21C) -0.11851 -1.00334 -0.10589 0.21 1.000 Uiso
H(22A) 0.98349 -0.12999 0.55127 0.17 1.000 Uiso
H(22B) 0.89189 -0.24019 0.59677 0.19 1.000 Uiso
H(22C) 0.90779 -0.08379 0.63657 0.21 1.000 Uiso
H(23A) 0.277(4) -0.036(4) 0.571(3) 0.06 1.000 Uiso
H(23B) 0.343(4) -0.007(5) 0.490(3) 0.06 1.000 Uiso
H(25A) 0.00421 -0.44504 0.23092 0.28 1.000 Uiso
H(25B) -0.09139 -0.43454 0.31042 0.11 1.000 Uiso
H(26A) 0.029(8) -0.608(7) 0.293(6) 0.13 1.000 Uiso
H(26B) -0.036(8) -0.559(10) 0.385(6) 0.14 1.000 Uiso
H(26C) -0.131(12) -0.672(12) 0.250(9) 0.22 1.000 Uiso
H(27A) 0.43732 -0.25112 0.96903 0.19 1.000 Uiso
H(27B) 0.49362 -0.33792 0.89003 0.21 1.000 Uiso
H(27C) 0.32982 -0.40222 0.86593 0.23 1.000 Uiso
H(20A) -0.00158 -0.80255 -0.13973 0.20 1.000 Uiso
H(20B) -0.07578 -0.73035 -0.06733 0.14 1.000 Uiso
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
_geom_angle_publ_flag
C(2) C(1) C(16) 109.9(3) 2_656 yes
C(2) C(1) H(1A) 110.1(23) . yes
C(2) C(1) H(1B) 111.0(28) . yes
C(16) C(1) H(1A) 110.2(24) . yes
C(16) C(1) H(1B) 109.9(29) . yes
H(1A) C(1) H(1B) 105.6(36) . yes
C(1) C(2) C(3) 120.5(4) . yes
C(1) C(2) C(7) 121.5(4) . yes
C(3) C(2) C(7) 117.8(3) . yes
C(2) C(3) C(4) 122.2(4) . yes
C(2) C(3) H(3) 121.6(27) . yes
C(4) C(3) H(3) 116.2(27) . yes
C(3) C(4) C(5) 118.0(4) . yes
C(3) C(4) C(22) 121.3(4) . yes
C(5) C(4) C(22) 120.6(4) . yes
C(4) C(5) C(6) 122.7(3) . yes
C(4) C(5) H(5) 119.0(28) . yes
C(6) C(5) H(5) 118.3(28) . yes
C(5) C(6) C(7) 117.6(3) . yes
C(5) C(6) C(8) 121.8(3) . yes
C(7) C(6) C(8) 120.6(3) . yes
C(2) C(7) C(6) 121.7(3) . yes
C(2) C(7) O(1) 118.1(3) . yes
C(6) C(7) O(1) 120.0(3) . yes
C(6) C(8) C(9) 113.3(3) . yes
C(6) C(8) H(8A) 108.8(21) . yes
C(6) C(8) H(8B) 107.9(24) . yes
C(9) C(8) H(8A) 104.4(21) . yes
C(9) C(8) H(8B) 112.0(22) . yes
H(8A) C(8) H(8B) 110.3(30) . yes
C(8) C(9) C(10) 121.8(3) . yes
C(8) C(9) C(14) 119.5(3) . yes
C(10) C(9) C(14) 118.6(3) . yes
C(9) C(10) C(11) 122.1(4) . yes
C(9) C(10) H(10) 119.3(20) . yes
C(11) C(10) H(10) 118.5(20) . yes
C(10) C(11) C(12) 117.3(4) . yes
C(10) C(11) C(27) 121.1(4) . yes
C(12) C(11) C(27) 121.5(4) . yes
C(11) C(12) C(13) 123.3(4) . yes
C(11) C(12) H(12) 118.8(26) . yes
C(13) C(12) H(12) 117.9(26) . yes
C(12) C(13) C(14) 117.2(3) . yes
C(12) C(13) C(15) 119.8(3) . yes
C(14) C(13) C(15) 122.9(3) . yes
C(9) C(14) C(13) 121.3(3) . yes
C(9) C(14) O(4) 116.0(3) . yes
C(13) C(14) O(4) 122.3(3) . yes
C(13) C(15) C(16) 116.4(3) . yes
C(13) C(15) H(15A) 105.2(21) . yes
C(13) C(15) H(15B) 104.0(21) . yes
C(16) C(15) H(15A) 110.3(21) . yes
C(16) C(15) H(15B) 109.4(21) . yes
H(15A)- C(15) H(15B) 111.3(29) . yes
C(1) C(16) C(15) 114.1(3) . yes
C(1) C(16) C(17) 120.9(4) . yes
C(15) C(16) C(17) 124.9(4) . yes
C(16) C(17) H(17A) 119.1(26) . yes
C(16) C(17) H(17B) 125.0(27) . yes
H(17A)- C(17) H(17B) 114.6(37) . yes
C(19) C(18) O(1) 109.4(4) . yes
C(19) C(18) H(18A) 111.5(40) . yes
C(19) C(18) H(18B) 109.2(37) . yes
O(1) C(18) H(18A) 114.1(40) . yes
O(1) C(18) H(18B) 115.3(41) . yes
H(18A)- C(18) H(18B) 96.8(58) . yes
C(18) C(19) O(2) 124.7(6) . yes
C(18) C(19) O(3) 110.9(5) . yes
O(2) C(19) O(3) 124.4(5) . yes
C(21) C(20) O(3) 109.5(9) . yes
C(21) C(20) H(20A) 110.6(9) . yes
C(21) C(20) H(20B) 108.0(10) . yes
O(3) C(20) H(20A) 109.6(8) . yes
O(3) C(20) H(20B) 110.0(8) . yes
H(20A)- C(20) H(20B) 109.0(10) . yes
C(20) C(21) H(21A) 107.8(15) . yes
C(20) C(21) H(21B) 110.6(13) . yes
C(20) C(21) H(21C) 108.0(12) . yes
H(21A)- C(21) H(21B) 110.7(13) . yes
H(21A)- C(21) H(21C) 110.7(14) . yes
H(21B)- C(21) H(21C) 109.0(16) . yes
C(4) C(22) H(22A) 120.4(5) . yes
C(4) C(22) H(22B) 107.6(4) . yes
C(4) C(22) H(22C) 105.9(4) . yes
H(22A)- C(22) H(22B) 106.8(5) . yes
H(22A)- C(22) H(22C) 106.8(5) . yes
H(22B)- C(22) H(22C) 109.1(5) . yes
C(24) C(23) O(4) 115.1(4) . yes
C(24) C(23) H(23A) 109.4(25) . yes
C(24) C(23) H(23B) 108.6(28) . yes
O(4) C(23) H(23A) 113.0(25) . yes
O(4) C(23) H(23B) 105.4(29) . yes
H(23A)- C(23) H(23B) 104.5(38) . yes
C(23) C(24) O(5) 123.0(4) . yes
C(23) C(24) O(6) 114.4(4) . yes
O(5) C(24) O(6) 122.5(5) . yes
C(26) C(25) O(6) 109.8(9) . yes
C(26) C(25) H(25A) 108.2(11) . yes
C(26) C(25) H(25B) 110.3(7) . yes
O(6) C(25) H(25A) 109.9(7) . yes
O(6) C(25) H(25B) 109.6(10) . yes
H(25A)- C(25) H(25B) 109.0(11) . yes
C(25) C(26) H(26A) 119.2(45) . yes
C(25) C(26) H(26B) 97.5(52) . yes
C(25) C(26) H(26C) 120.5(70) . yes
H(26A)- C(26) H(26B) 102.1(64) . yes
H(26A)- C(26) H(26C) 106.8(82) . yes
H(26B)- C(26) H(26C) 108.0(81) . yes
C(11) C(27) H(27A) 121.0(5) . yes
C(11) C(27) H(27B) 106.4(5) . yes
C(11) C(27) H(27C) 106.5(4) . yes
H(27A)- C(27) H(27B) 106.8(5) . yes
H(27A)- C(27) H(27C) 106.8(5) . yes
H(27B)- C(27) H(27C) 109.0(5) . yes
C(7) O(1) C(18) 114.8(3) . yes
C(19) O(3) C(20) 117.0(6) . yes
C(14) O(4) C(23) 119.0(3) . yes
C(24) O(6) C(25) 116.9(5) . yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C(1) C(2) 1.515(5) 1_555 1_555 yes
C(1) C(16) 1.529(5) 1_555 2_656 yes
C(1) H(1A) 0.97(4) . . yes
C(1) H(1B) 0.88(5) . . yes
C(2) C(3) 1.400(5) . . yes
C(2) C(7) 1.398(5) . . yes
C(3) C(4) 1.379(6) . . yes
C(3) H(3) 0.90(5) . . yes
C(4) C(5) 1.390(5) . . yes
C(4) C(22) 1.503(5) . . yes
C(5) C(6) 1.390(5) . . yes
C(5) H(5) 0.98(5) . . yes
C(6) C(7) 1.399(5) . . yes
C(6) C(8) 1.507(5) . . yes
C(7) O(1) 1.393(4) . . yes
C(8) C(9) 1.511(5) . . yes
C(8) H(8A) 0.97(4) . . yes
C(8) H(8B) 0.90(5) . . yes
C(9) C(10) 1.387(5) . . yes
C(9) C(14) 1.406(5) . . yes
C(10) C(11) 1.386(5) . . yes
C(10) H(10) 0.98(4) . . yes
C(11) C(12) 1.389(5) . . yes
C(11) C(27) 1.509(6) . . yes
C(12) C(13) 1.398(5) . . yes
C(12) H(12) 0.92(4) . . yes
C(13) C(14) 1.390(5) . . yes
C(13) C(15) 1.523(5) . . yes
C(14) O(4) 1.385(4) . . yes
C(15) C(16) 1.502(6) . . yes
C(15) H(15A) 1.03(4) . . yes
C(15) H(15B) 0.93(4) . . yes
C(16) C(17) 1.309(6) . . yes
C(17) H(17A) 0.98(5) . . yes
C(17) H(17B) 1.01(6) . . yes
C(18) C(19) 1.490(7) . . yes
C(18) O(1) 1.405(5) . . yes
C(18) H(18A) 0.89(7) . . yes
C(18) H(18B) 0.98(8) . . yes
C(19) O(2) 1.180(8) . . yes
C(19) O(3) 1.319(7) . . yes
C(20) C(21) 1.421(19) . . yes
C(20) O(3) 1.463(9) . . yes
C(20) H(20A) 0.960(10) . . yes
C(20) H(20B) 0.960(10) . . yes
C(21) H(21A) 0.960(11) . . yes
C(21) H(21B) 0.960(13) . . yes
C(21) H(21C) 0.960(18) . . yes
C(22) H(22A) 0.961(5) . . yes
C(22) H(22B) 0.960(5) . . yes
C(22) H(22C) 0.960(5) . . yes
C(23) C(24) 1.483(5) . . yes
C(23) O(4) 1.424(5) . . yes
C(23) H(23A) 0.91(5) . . yes
C(23) H(23B) 0.84(5) . . yes
C(24) O(5) 1.196(6) . . yes
C(24) O(6) 1.306(5) . . yes
C(25) C(26) 1.384(11) . . yes
C(25) O(6) 1.481(10) . . yes
C(25) H(25A) 0.960(15) . . yes
C(25) H(25B) 0.960(8) . . yes
C(26) H(26A) 0.92(8) . . yes
C(26) H(26B) 1.03(8) . . yes
C(26) H(26C) 0.96(11) . . yes
C(27) H(27A) 0.960(5) . . yes
C(27) H(27B) 0.960(6) . . yes
C(27) H(27C) 0.960(6) . . yes
