#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/36/2223627.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_2223627
loop_
_publ_author_name
'Pereira Silva, P. S.'
'Ghalib, Raza Murad'
'Mehdi, Sayed Hasan'
'Hashim, Rokiah'
'Sulaiman, Othman'
_publ_section_title
;Redetermination of ethyl
 (3a-cis)-3a,8b-dihydroxy-2-methyl-4-oxo-3a,8b-dihydro-4H-indeno[1,2-b]furan-3-carboxylate
 monohydrate
;
_journal_coeditor_code           BT5075
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2616
_journal_paper_doi               10.1107/S1600536809039403
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H14 O6, H2 O1'
_chemical_formula_moiety         'C15 H14 O6, H2 O1'
_chemical_formula_sum            'C15 H16 O7'
_chemical_formula_weight         308.28
_chemical_melting_point_gt       373
_chemical_melting_point_lt       376
_chemical_name_systematic
;
ethyl (3a-cis)-3a,8b-dihydroxy-2-methyl-
4-oxo-3a,8b-dihydro-4H-indeno[1,2-b]furan-3-carboxylate
monohydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 98.833(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9740(4)
_cell_length_b                   16.7524(8)
_cell_length_c                   11.0041(5)
_cell_measurement_reflns_used    5159
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.8569
_cell_measurement_theta_min      2.2329
_cell_volume                     1452.53(12)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'APEX2 (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0127
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            21608
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.98
_diffrn_reflns_theta_min         2.23
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepipedic
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.382
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3509
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0553
_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)+(0.0682P)²+0.9584P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1407
_refine_ls_wR_factor_ref         0.1543
_reflns_number_gt                2820
_reflns_number_total             3509
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5075.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2223627
_cod_database_fobs_code          2223627
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'
loop_
_atom_site_type_symbol
_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
O O8 0.60398(14) 0.49466(7) 0.73529(11) 0.0366(3) Uani d . 1 . .
O O13 0.19037(18) 0.31575(9) 0.78551(16) 0.0590(4) Uani d . 1 A .
O O14 0.69530(14) 0.43316(7) 0.92132(11) 0.0353(3) Uani d . 1 . .
H H14 0.6687 0.4710 0.9617 0.053 Uiso calc R 1 . .
O O17 0.04534(18) 0.49231(10) 0.79040(16) 0.0641(5) Uani d . 1 . .
O O18 0.10479(19) 0.57149(12) 0.64190(19) 0.0820(6) Uani d D 1 . .
O O21 0.36289(15) 0.43437(7) 0.95007(10) 0.0354(3) Uani d . 1 . .
H H21 0.2683 0.4176 0.9572 0.053 Uiso calc R 1 . .
C C1 0.4633(2) 0.30757(10) 0.71894(16) 0.0368(4) Uani d . 1 A .
C C2 0.4601(3) 0.23627(12) 0.65306(19) 0.0488(5) Uani d . 1 . .
H H2 0.3606 0.2069 0.6338 0.059 Uiso calc R 1 . .
C C3 0.6090(3) 0.21116(13) 0.6179(2) 0.0568(5) Uani d . 1 . .
H H3 0.6102 0.1642 0.5729 0.068 Uiso calc R 1 . .
C C4 0.7575(3) 0.25430(13) 0.6479(2) 0.0552(5) Uani d . 1 . .
H H4 0.8572 0.2349 0.6247 0.066 Uiso calc R 1 . .
C C5 0.7612(2) 0.32559(12) 0.71189(18) 0.0443(4) Uani d . 1 . .
H H5 0.8609 0.3549 0.7308 0.053 Uiso calc R 1 . .
C C6 0.6107(2) 0.35153(10) 0.74655(15) 0.0331(3) Uani d . 1 . .
C C7 0.58235(19) 0.42670(9) 0.81511(15) 0.0298(3) Uani d . 1 . .
C C9 0.4506(2) 0.52675(10) 0.69420(16) 0.0353(4) Uani d . 1 A .
C C10 0.3220(2) 0.49272(10) 0.74201(15) 0.0349(4) Uani d . 1 . .
C C11 0.38915(19) 0.42608(9) 0.82712(14) 0.0295(3) Uani d . 1 A .
C C12 0.3265(2) 0.34408(10) 0.77556(16) 0.0364(4) Uani d . 1 . .
C C15 0.4550(3) 0.59275(13) 0.6050(2) 0.0521(5) Uani d . 1 . .
H H15A 0.4636 0.5710 0.5255 0.078 Uiso calc R 1 A .
H H15B 0.5514 0.6262 0.6316 0.078 Uiso calc R 1 . .
H H15C 0.3530 0.6237 0.6003 0.078 Uiso calc R 1 . .
C C16 0.1456(2) 0.51738(12) 0.72845(19) 0.0473(5) Uani d . 1 A .
C C19A -0.0681(3) 0.6050(2) 0.6333(4) 0.0752(11) Uani d PDU 0.815(6) A 1
H H19A -0.1528 0.5633 0.6168 0.090 Uiso calc PR 0.815(6) A 1
H H19B -0.0826 0.6318 0.7092 0.090 Uiso calc PR 0.815(6) A 1
C C20A -0.0827(4) 0.6619(2) 0.5313(4) 0.0808(11) Uani d PDU 0.815(6) A 1
H H20A -0.1885 0.6900 0.5258 0.121 Uiso calc PR 0.815(6) A 1
H H20B -0.0787 0.6336 0.4559 0.121 Uiso calc PR 0.815(6) A 1
H H22C 0.0094 0.6993 0.5452 0.121 Uiso calc PR 0.815(6) A 1
C C19B -0.0660(10) 0.5823(6) 0.5692(13) 0.0752(11) Uani d PDU 0.185(6) A 2
H H19C -0.0656 0.5693 0.4833 0.090 Uiso calc PR 0.185(6) A 2
H H19D -0.1491 0.5491 0.6008 0.090 Uiso calc PR 0.185(6) A 2
C C20B -0.1022(16) 0.6673(7) 0.5842(16) 0.0808(11) Uani d PDU 0.185(6) A 2
H H20D -0.2188 0.6779 0.5520 0.121 Uiso calc PR 0.185(6) A 2
H H20E -0.0302 0.6988 0.5406 0.121 Uiso calc PR 0.185(6) A 2
H H20F -0.0811 0.6809 0.6700 0.121 Uiso calc PR 0.185(6) A 2
O O22 0.0700(2) 0.39329(12) 1.03321(17) 0.0620(4) Uani d . 1 . .
H H22A -0.014(4) 0.385(2) 0.981(3) 0.093 Uiso d . 1 . .
H H22B 0.057(4) 0.4267(19) 1.094(3) 0.093 Uiso d . 1 . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 O8 C7 . . 109.07(12) ?
C7 O14 H14 . . 109.5 ?
C16 O18 C19A . . 115.58(18) ?
C16 O18 C19B . . 125.4(6) ?
C19A O18 C19B . . 31.6(5) ?
C11 O21 H21 . . 109.5 ?
C6 C1 C2 . . 121.21(17) ?
C6 C1 C12 . . 110.30(15) ?
C2 C1 C12 . . 128.35(17) ?
C3 C2 C1 . . 117.51(19) ?
C3 C2 H2 . . 121.2 ?
C1 C2 H2 . . 121.2 ?
C2 C3 C4 . . 121.28(18) ?
C2 C3 H3 . . 119.4 ?
C4 C3 H3 . . 119.4 ?
C3 C4 C5 . . 121.52(19) ?
C3 C4 H4 . . 119.2 ?
C5 C4 H4 . . 119.2 ?
C6 C5 C4 . . 117.34(18) ?
C6 C5 H5 . . 121.3 ?
C4 C5 H5 . . 121.3 ?
C1 C6 C5 . . 121.12(16) ?
C1 C6 C7 . . 111.65(14) ?
C5 C6 C7 . . 127.23(16) ?
O14 C7 O8 . . 109.19(12) ?
O14 C7 C6 . . 111.45(13) ?
O8 C7 C6 . . 108.04(13) ?
O14 C7 C11 . . 117.14(13) ?
O8 C7 C11 . . 105.29(12) ?
C6 C7 C11 . . 105.22(12) ?
O8 C9 C10 . . 113.90(15) ?
O8 C9 C15 . . 113.99(15) ?
C10 C9 C15 . . 132.10(17) ?
C9 C10 C16 . . 128.49(16) ?
C9 C10 C11 . . 109.76(14) ?
C16 C10 C11 . . 121.49(15) ?
O21 C11 C10 . . 115.77(13) ?
O21 C11 C12 . . 110.76(13) ?
C10 C11 C12 . . 111.65(13) ?
O21 C11 C7 . . 111.96(12) ?
C10 C11 C7 . . 101.73(12) ?
C12 C11 C7 . . 104.03(12) ?
O13 C12 C1 . . 127.76(16) ?
O13 C12 C11 . . 124.31(16) ?
C1 C12 C11 . . 107.89(13) ?
C9 C15 H15A . . 109.5 ?
C9 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C9 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
O17 C16 O18 . . 122.50(18) ?
O17 C16 C10 . . 124.07(18) ?
O18 C16 C10 . . 113.43(16) ?
C20A C19A O18 . . 105.1(2) ?
C20A C19A H19A . . 110.7 ?
O18 C19A H19A . . 110.7 ?
C20A C19A H19B . . 110.7 ?
O18 C19A H19B . . 110.7 ?
H19A C19A H19B . . 108.8 ?
C19A C20A H20A . . 109.5 ?
C19A C20A H20B . . 109.5 ?
H20A C20A H20B . . 109.5 ?
C19A C20A H22C . . 109.5 ?
H20A C20A H22C . . 109.5 ?
H20B C20A H22C . . 109.5 ?
C20B C19B O18 . . 103.8(5) ?
C20B C19B H19C . . 111.0 ?
O18 C19B H19C . . 111.0 ?
C20B C19B H19D . . 111.0 ?
O18 C19B H19D . . 111.0 ?
H19C C19B H19D . . 109.0 ?
C19B C20B H20D . . 109.5 ?
C19B C20B H20E . . 109.5 ?
H20D C20B H20E . . 109.5 ?
C19B C20B H20F . . 109.5 ?
H20D C20B H20F . . 109.5 ?
H20E C20B H20F . . 109.5 ?
H22A O22 H22B . . 117(3) ?
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
O8 C9 . 1.349(2) ?
O8 C7 . 1.4643(19) ?
O13 C12 . 1.205(2) ?
O14 C7 . 1.3658(19) ?
O14 H14 . 0.8200 ?
O17 C16 . 1.203(2) ?
O18 C16 . 1.319(2) ?
O18 C19A . 1.478(3) ?
O18 C19B . 1.481(5) ?
O21 C11 . 1.4073(19) ?
O21 H21 . 0.8200 ?
C1 C6 . 1.380(2) ?
C1 C2 . 1.395(2) ?
C1 C12 . 1.470(2) ?
C2 C3 . 1.370(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.384(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.384(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.384(2) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.503(2) ?
C7 C11 . 1.566(2) ?
C9 C10 . 1.349(2) ?
C9 C15 . 1.482(3) ?
C10 C16 . 1.452(2) ?
C10 C11 . 1.502(2) ?
C11 C12 . 1.540(2) ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C19A C20A . 1.463(4) ?
C19A H19A . 0.9700 ?
C19A H19B . 0.9700 ?
C20A H20A . 0.9600 ?
C20A H20B . 0.9600 ?
C20A H22C . 0.9600 ?
C19B C20B . 1.468(6) ?
C19B H19C . 0.9700 ?
C19B H19D . 0.9700 ?
C20B H20D . 0.9600 ?
C20B H20E . 0.9600 ?
C20B H20F . 0.9600 ?
O22 H22A . 0.83(3) ?
O22 H22B . 0.89(3) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O14 H14 O21 3_667 0.82 1.90 2.7103(17) 171.5
O21 H21 O22 . 0.82 1.94 2.724(2) 159.2
O22 H22A O14 1_455 0.83(3) 2.45(3) 3.124(2) 140(3)
O22 H22B O17 3_567 0.89(3) 2.11(3) 2.972(3) 163(3)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0.6(3) ?
C12 C1 C2 C3 . . . . -174.61(19) ?
C1 C2 C3 C4 . . . . 0.9(3) ?
C2 C3 C4 C5 . . . . -1.7(4) ?
C3 C4 C5 C6 . . . . 1.1(3) ?
C2 C1 C6 C5 . . . . -1.3(3) ?
C12 C1 C6 C5 . . . . 174.74(16) ?
C2 C1 C6 C7 . . . . 178.60(16) ?
C12 C1 C6 C7 . . . . -5.4(2) ?
C4 C5 C6 C1 . . . . 0.4(3) ?
C4 C5 C6 C7 . . . . -179.43(17) ?
C9 O8 C7 O14 . . . . -131.60(14) ?
C9 O8 C7 C6 . . . . 107.02(14) ?
C9 O8 C7 C11 . . . . -5.02(16) ?
C1 C6 C7 O14 . . . . 127.18(15) ?
C5 C6 C7 O14 . . . . -52.9(2) ?
C1 C6 C7 O8 . . . . -112.85(15) ?
C5 C6 C7 O8 . . . . 67.0(2) ?
C1 C6 C7 C11 . . . . -0.76(18) ?
C5 C6 C7 C11 . . . . 179.11(17) ?
C7 O8 C9 C10 . . . . 4.1(2) ?
C7 O8 C9 C15 . . . . -175.85(15) ?
O8 C9 C10 C16 . . . . 172.92(18) ?
C15 C9 C10 C16 . . . . -7.1(3) ?
O8 C9 C10 C11 . . . . -1.3(2) ?
C15 C9 C10 C11 . . . . 178.71(19) ?
C9 C10 C11 O21 . . . . 119.75(16) ?
C16 C10 C11 O21 . . . . -54.9(2) ?
C9 C10 C11 C12 . . . . -112.29(16) ?
C16 C10 C11 C12 . . . . 73.0(2) ?
C9 C10 C11 C7 . . . . -1.87(18) ?
C16 C10 C11 C7 . . . . -176.54(16) ?
O14 C7 C11 O21 . . . . 1.34(19) ?
O8 C7 C11 O21 . . . . -120.20(13) ?
C6 C7 C11 O21 . . . . 125.78(13) ?
O14 C7 C11 C10 . . . . 125.58(14) ?
O8 C7 C11 C10 . . . . 4.03(15) ?
C6 C7 C11 C10 . . . . -109.99(14) ?
O14 C7 C11 C12 . . . . -118.30(14) ?
O8 C7 C11 C12 . . . . 120.15(13) ?
C6 C7 C11 C12 . . . . 6.13(16) ?
C6 C1 C12 O13 . . . . -168.21(19) ?
C2 C1 C12 O13 . . . . 7.4(3) ?
C6 C1 C12 C11 . . . . 9.40(19) ?
C2 C1 C12 C11 . . . . -174.95(18) ?
O21 C11 C12 O13 . . . . 47.9(2) ?
C10 C11 C12 O13 . . . . -82.7(2) ?
C7 C11 C12 O13 . . . . 168.40(18) ?
O21 C11 C12 C1 . . . . -129.76(14) ?
C10 C11 C12 C1 . . . . 99.64(15) ?
C7 C11 C12 C1 . . . . -9.31(17) ?
C19A O18 C16 O17 . . . . 5.4(4) ?
C19B O18 C16 O17 . . . . -29.6(7) ?
C19A O18 C16 C10 . . . . -173.7(3) ?
C19B O18 C16 C10 . . . . 151.3(7) ?
C9 C10 C16 O17 . . . . -166.7(2) ?
C11 C10 C16 O17 . . . . 6.9(3) ?
C9 C10 C16 O18 . . . . 12.3(3) ?
C11 C10 C16 O18 . . . . -174.08(18) ?
C16 O18 C19A C20A . . . . -179.3(3) ?
C19B O18 C19A C20A . . . . -62.8(10) ?
C16 O18 C19B C20B . . . . 127.2(10) ?
C19A O18 C19B C20B . . . . 45.5(9) ?
