#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/03/2010337.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2010337
loop_
_publ_author_name
'Paulus, E.F.'
'Dornberger, K.'
'Werner, W.'
'Fenske, D.'
_publ_section_title
;
 Madurahydroxylactone
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2064
_journal_page_last               2067
_journal_paper_doi               10.1107/S0108270194003185
_journal_volume                  50
_journal_year                    1994
_chemical_formula_moiety         'C26 H18 O10,C2 H3 N1'
_chemical_formula_sum            'C28 H21 N O10'
_chemical_formula_weight         531.48
_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_type_scat_source           IntTabIV
_cell_angle_alpha                90.
_cell_angle_beta                 103.95(5)
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   12.849(3)
_cell_length_b                   12.675(3)
_cell_length_c                   15.076(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      12.3
_cell_measurement_theta_min      2.3
_cell_volume                     2382.9(11)
_diffrn_measurement_device       'One circle with image plate (Stoe)'
_diffrn_measurement_method       XX
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.148
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            31701
_diffrn_reflns_theta_max         25.8
_diffrn_standards_number         No
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_description       needle
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.37
_refine_diff_density_min         -0.43
_refine_ls_goodness_of_fit_obs   2.22
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     364
_refine_ls_number_reflns         4207
_refine_ls_R_factor_obs          0.149
_refine_ls_shift/esd_max         0.004
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      unit
_refine_ls_wR_factor_obs         0.120
_reflns_number_observed          4201
_reflns_number_total             4211
_reflns_observed_criterion       F>\s(F)
_cod_data_source_file            se1045.cif
_cod_data_source_block           se1045a
_cod_original_cell_volume        2382.9
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C28 H21 N1 O10'
_cod_database_code               2010337
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2+x,1/2-y,1/2+z
-x,-y,-z
1/2-x,1/2+y,1/2-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
C(01) .4095(5) .4237(5) .5894(4) 0.47(2)
C(02) .2996(5) .4482(5) .5630(4) .047(2)
C(03) .2363(5) .4241(5) .4774(4) .049(2)
C(04) .2852(5) .3756(5) .4142(4) .047(2)
C(05) .3970(5) .3526(5) .4362(4) .046(2)
C(06) .4573(4) .3764(5) .5257(4) .042(2)
C(07) .4453(5) .3062(5) .3679(5) .053(2)
C(08) .5633(5) .2851(5) .3930(4) .045(2)
C(09) .6233(4) .3041(5) .4843(4) .042(2)
C(10) .5735(5) .3518(5) .5521(4) .047(2)
C(11) .6185(5) .2504(5) .3286(4) .043(2)
C(12) .7299(5) .2301(4) .3542(4) .041(2)
C(13) .7862(5) .2344(5) .4462(4) .042(2)
C(14) .7333(5) .2794(5) .5101(4) .045(2)
C(15) .7923(5) .2083(5) .2838(4) .046(2)
C(16) .9061(5) .2550(5) .3138(4) .050(2)
C(17) .9596(5) .2075(5) .4060(4) .048(2)
C(18) .8984(4) .1962(5) .4707(4) .042(2)
C(19) 1.0670(5) .1747(5) .4242(4) .052(2)
C(20) 1.1108(5) .1290(5) .5072(4) .047(2)
C(21) 1.0513(4) .1127(5) .5711(4) .043(2)
C(22) .9425(5) .1435(5) .5527(4) .043(2)
C(23) .1184(5) .4508(6) .4539(5) .058(2)
C(24) .5432(5) .1342(5) .2080(5) .057(2)
C(25) 1.2237(5) .0892(6) .5485(4) .054(2)
C(26) 1.1163(5) .0627(5) .6534(5) .052(2)
O(01) 0.2505(3) .4977(3) .6227(3) .0340(10)
O(02) .2223(3) .3527(4) .3304(3) .0380(10)
O(03) .3905(3) .2857(5) .2899(3) .053(2)
O(04) .6249(3) .3723(4) .6316(3) .040(2)
O(05) .5688(3) .2409(3) .2375(3) .0320(10)
O(06) .7929(3) .3047(3) .5940(3) .0360(10)
O(07) .8838(3) .1151(3) .6133(3) .0320(10)
O(08) 1.2966(3) .1681(4) .5553(3) .050(2)
O(09) 1.2180(3) .0516(3) .6406(3) .0360(10)
O(10) 1.0950(3) .0351(3) .7227(3) .0360(10)
C(1) 1.6818(8) -.0303(9) .6638(8) .091(4)
C(2) 1.5862(8) .0308(9) .6321(7) .095(4)
N(1) 1.5058(8) .0774(9) .6042(7) .166(5)
H(231) .0998 .4837 .5053 .080
H(232) .1018 .4977 .4024 .080
H(233) .0781 .3867 .4390 .080
H(241) .5081 .1332 .1441 .080
H(242) .6084 .0941 .2181 .080
H(243) .4969 .1038 .2424 .080
H(01A) .2965 .5108 .6723 .080
H(02) .2614 .3257 .2982 .080
H(06) .7531 .3320 .6254 .080
H(07) .8441 .1668 .6199 .080
H(08) 1.3586 .1434 .5786 .080
H(01) .4658 .4362 .6526 .050
H(151) .7521 .2386 .2265 .050
H(152) .7947 .1204 .2734 .050
H(161) .9533 .2426 .2600 .050
H(162) .8917 .3389 .3186 .050
H(19) 1.1156 .1824 .3819 .050
H(25) 1.2613 .0295 .5092 .050
H(11) 1.747(10) .032(10) .652(9) .18(5)
H(12) 1.701(10) -.023(11) .755(10) .21(6)
H(13) 1.656(11) -.117(12) .614(10) .22(6)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(02) C(01) C(06) 118.6(5) yes
C(01) C(02) C(03) 122.6(6) yes
C(01) C(02) O(01) 120.3(5) yes
C(03) C(02) O(01) 117.1(5) yes
C(02) C(03) C(04) 118.2(5) yes
C(02) C(03) C(23) 120.0(6) yes
C(04) C(03) C(23) 121.8(5) yes
C(03) C(04) C(05) 121.6(5) yes
C(03) C(04) O(02) 117.6(5) yes
C(05) C(04) O(02) 120.8(6) yes
C(04) C(05) C(06) 117.8(6) yes
C(04) C(05) C(07) 119.9(5) yes
C(06) C(05) C(07) 122.3(5) yes
C(01) C(06) C(05) 121.1(5) yes
C(01) C(06) C(10) 119.2(5) yes
C(05) C(06) C(10) 119.6(5) yes
C(05) C(07) C(08) 118.4(5) yes
C(05) C(07) O(03) 121.0(6) yes
C(08) C(07) O(03) 120.6(6) yes
C(07) C(08) C(09) 119.5(6) yes
C(07) C(08) C(11) 122.1(5) yes
C(09) C(08) C(11) 118.4(5) yes
C(08) C(09) C(10) 121.3(5) yes
C(08) C(09) C(14) 120.1(6) yes
C(10) C(09) C14) 118.6(5) yes
C(06) C(10) C(09) 118.8(5) yes
C(06) C(10) O(04) 118.7(6) yes
C(09) C(10) O(04) 122.5(5) yes
C(08) C(11) C(12) 121.0(5) yes
C(08) C(11) O(05) 121.9(5) yes
C(12) C(11) O(05) 117.0(5) yes
C(11) C(12) C(13) 120.7(6) yes
C(11) C(12) C(15) 121.2(5) yes
C(13) C(12) C(15) 118.1(5) yes
C(12) C(13) C(14) 117.9(5) yes
C(12) C(13) C(18) 118.2(5) yes
C(14) C(13) C(18) 123.8(5) yes
C(09) C(14) C(13) 120.9(5) yes
C(09) C(14) O(06) 120.7(6) yes
C(13) C(14) O(06) 118.3(5) yes
C(12) C(15) C(16) 110.6(5) yes
C(15) C(16) C(17) 107.7(5) yes
C(16) C(17) C(18) 118.2(5) yes
C(16) C(17) C(19) 120.2(6) yes
C(18) C(17) C(19) 121.7(5) yes
C(13) C(18) C(17) 117.9(5) yes
C(13) C(18) C(22) 122.7(6) yes
C(17) C(18) C(22) 119.2(5) yes
C(17) C(19) C(20) 118.1(6) yes
C(19) C(20) C(21) 121.7(6) yes
C(19) C(20) C(25) 131.0(6) yes
C(21) C(20) C(25) 107.3(5) yes
C(20) C(21) C(22) 120.5(5) yes
C(20) C(21) C(26) 111.0(5) yes
C(22) C(21) C(26) 128.5(6) yes
C(18) C(22) C(21) 118.5(6) yes
C(18) C(22) O(07) 123.0(5) yes
C(21) C(22) O(07) 118.4(5) yes
C(20) C(25) O(08) 111.1(5) yes
C(20) C(25) O(09) 103.4(5) yes
O(08) C(25) O(09) 110.8(5) yes
C(21) C(26) O(09) 107.1(6) yes
C(21) C(26) O(10) 131.6(6) yes
O(09) C(26) O(10) 121.3(5) yes
C(11) O(05) C(24) 114.1(4) yes
C(25) O(09) C(26) 111.2(4) yes
C(1) C(2) N(1) 177.3(11) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C(01) C(02) . . 1.406(8) yes
C(01) C(06) . . 1.394(9) yes
C(02) C(03) . . 1.383(8) yes
C(02) O(01) . . 1.370(8) yes
C(03) C(04) . . 1.402(9) yes
C(03) C(23) . . 1.510(8) yes
C(04) C(05) . . 1.425(8) yes
C(04) O(02) . . 1.357(7) yes
C(05) C(06) . . 1.417(7) yes
C(05) C(07) . . 1.448(10) yes
C(06) C(10) . . 1.483(8) yes
C(07) C(08) . . 1.496(8) yes
C(07) O(03) . . 1.245(7) yes
C(08) C(09) . . 1.427(7) yes
C(08) C(11) . . 1.404(9) yes
C(09) C(10) . . 1.461(9) yes
C(09) C(14) . . 1.408(8) yes
C(10) O(04) . . 1.248(7) yes
C(11) C(12) . . 1.414(8) yes
C(11) O(05) . . 1.373(6) yes
C(12) C(13) . . 1.402(7) yes
C(12) C(15) . . 1.503(9) yes
C(13) C(14) . . 1.424(9) yes
C(13) C(18) . . 1.480(8) yes
C(14) O(06) . . 1.350(6) yes
C(15) C(16) . . 1.540(8) yes
C(16) C(17) . . 1.519(8) yes
C(17) C(18) . . 1.400(9) yes
C(17) C(19) . . 1.403(9) yes
C(18) C(22) . . 1.398(8) yes
C(19) C(20) . . 1.370(8) yes
C(20) C(21) . . 1.383(9) yes
C(20) C(25) . . 1.521(8) yes
C(21) C(22) . . 1.414(8) yes
C(21) C(26) . . 1.462(8) yes
C(22) O(07) . . 1.365(8) yes
C(24) O(05) . . 1.437(8) yes
C(25) O(08) . . 1.357(8) yes
C(25) O(09) . . 1.487(8) yes
C(26) O(09) . . 1.373(8) yes
C(26) O(10) . . 1.195(9) yes
C(1) C(2) . . 1.433(14) yes
C(2) N(1) . . 1.177(14) yes
