#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2007328.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_2007328
loop_
_publ_author_name
'Parvez, M.'
'Sultana, N.'
'Sarfaraz, T. B.'
'Husain, S. A.'
_publ_section_title
;
 7-Oxaspiro[5.9]pentadecane-1,8,13-trione
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              789
_journal_page_last               790
_journal_volume                  54
_journal_year                    1998
_chemical_formula_analytical     'C14 H20 O4'
_chemical_formula_moiety         'C14 H20 O4'
_chemical_formula_structural     'C14 H20 O4'
_chemical_formula_sum            'C14 H20 O4'
_chemical_formula_weight         252.30
_chemical_melting_point          402.5(5)
_chemical_name_common            'macrocyclic lactone'
_chemical_name_systematic
;
7-Oxa-spiro[5,9]pentadecane-1,8,13-trione
;
_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'
_cell_angle_alpha                90.00
_cell_angle_beta                 97.02(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.667(3)
_cell_length_b                   7.292(2)
_cell_length_c                   15.275(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    200.0(10)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      18
_cell_volume                     1289.8(5)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software (Molecular Structure
Corporation, 1988)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1994)'
_computing_molecular_graphics    TEXSAN
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SAPI91 (Fan, 1991)'
_diffrn_ambient_temperature      200.0(10)
_diffrn_measurement_device       'Rigaku AFC-6S'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.046
_diffrn_reflns_av_sigmaI/netI    0.031
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            2395
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         4.0
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  180
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       'block, cut from a large needle'
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.235
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.160
_refine_ls_goodness_of_fit_obs   1.171
_refine_ls_hydrogen_treatment    'H atoms riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2273
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.278
_refine_ls_restrained_S_obs      1.171
_refine_ls_R_factor_all          0.066
_refine_ls_R_factor_obs          0.037
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.05P)^2^+0.65P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.139
_refine_ls_wR_factor_obs         0.107
_reflns_number_observed          1662
_reflns_number_total             2279
_reflns_observed_criterion       I>2\s(I)
_[local]_cod_data_source_file    fg1408.cif
_[local]_cod_data_source_block   trione
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '402-403' was changed to '402.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2007328
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.0194(7) 0.0248(7) 0.0283(7) -0.0008(6) 0.0006(5) 0.0026(6)
O2 0.0371(9) 0.0288(8) 0.0335(8) -0.0048(7) 0.0047(7) 0.0045(7)
O3 0.0543(11) 0.0367(10) 0.0572(11) -0.0127(8) 0.0200(9) 0.0042(8)
O4 0.0268(8) 0.0490(10) 0.0485(10) -0.0105(7) 0.0100(7) -0.0038(8)
C1 0.0300(11) 0.0214(10) 0.0259(11) -0.0016(9) -0.0005(8) -0.0031(9)
C2 0.0305(12) 0.0358(13) 0.0452(14) 0.0032(10) -0.0072(10) 0.0028(11)
C3 0.0235(11) 0.0471(14) 0.0408(13) -0.0029(10) 0.0004(9) -0.0018(11)
C4 0.0370(13) 0.0481(15) 0.0388(13) -0.0124(11) -0.0024(10) -0.0045(12)
C5 0.0417(13) 0.0383(13) 0.0297(12) -0.0131(11) 0.0049(10) -0.0085(10)
C6 0.0455(13) 0.0219(11) 0.0376(12) -0.0112(10) 0.0119(10) -0.0093(10)
C7 0.0475(14) 0.0230(11) 0.0383(13) 0.0010(10) 0.0102(10) -0.0042(10)
C8 0.0285(11) 0.0292(11) 0.0335(12) 0.0008(9) 0.0069(9) -0.0033(9)
C9 0.0169(10) 0.0250(10) 0.0300(11) 0.0021(8) 0.0021(8) 0.0016(9)
C10 0.0231(11) 0.0304(11) 0.0297(11) -0.0019(9) -0.0012(8) 0.0045(9)
C11 0.0298(12) 0.0317(12) 0.0402(13) -0.0046(9) -0.0010(9) -0.0067(10)
C12 0.0342(13) 0.052(2) 0.0312(12) 0.0032(11) -0.0030(10) -0.0083(11)
C13 0.0342(12) 0.0447(14) 0.0238(11) 0.0066(10) 0.0011(9) 0.0050(10)
C14 0.0282(11) 0.0308(12) 0.0315(12) 0.0043(9) 0.0022(9) 0.0052(9)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
O1 0.58907(11) -0.0067(2) 0.31011(9) 0.0244(3) Uani d . 1 O
O2 0.54527(13) -0.2154(2) 0.40902(10) 0.0331(4) Uani d . 1 O
O3 0.6927(2) 0.4052(2) 0.34343(12) 0.0483(5) Uani d . 1 O
O4 0.29805(13) -0.1276(2) 0.30529(11) 0.0410(4) Uani d . 1 O
C1 0.6166(2) -0.1320(3) 0.37420(13) 0.0261(5) Uani d . 1 C
C2 0.7452(2) -0.1562(3) 0.3932(2) 0.0381(6) Uani d . 1 C
C3 0.8171(2) 0.0180(3) 0.3943(2) 0.0374(6) Uani d . 1 C
C4 0.8036(2) 0.1513(4) 0.4694(2) 0.0419(6) Uani d . 1 C
C5 0.6825(2) 0.2273(3) 0.47311(15) 0.0365(6) Uani d . 1 C
C6 0.6320(2) 0.3323(3) 0.3923(2) 0.0344(5) Uani d . 1 C
C7 0.5018(2) 0.3513(3) 0.3770(2) 0.0358(6) Uani d . 1 C
C8 0.4339(2) 0.1708(3) 0.36311(14) 0.0301(5) Uani d . 1 C
C9 0.4676(2) 0.0494(3) 0.29005(13) 0.0240(5) Uani d . 1 C
C10 0.3887(2) -0.1199(3) 0.27442(13) 0.0281(5) Uani d . 1 C
C11 0.4208(2) -0.2528(3) 0.20653(15) 0.0344(5) Uani d . 1 C
C12 0.4161(2) -0.1495(4) 0.11879(15) 0.0397(6) Uani d . 1 C
C13 0.4949(2) 0.0179(3) 0.12826(13) 0.0345(5) Uani d . 1 C
C14 0.4644(2) 0.1459(3) 0.20079(14) 0.0303(5) Uani d . 1 C
H2A 0.7695 -0.2368 0.3502 0.043(2) Uiso calc R 1 H
H2B 0.7617 -0.2145 0.4490 0.043(2) Uiso calc R 1 H
H3A 0.7973 0.0803 0.3399 0.043(2) Uiso calc R 1 H
H3B 0.8962 -0.0157 0.3975 0.043(2) Uiso calc R 1 H
H4A 0.8277 0.0909 0.5236 0.043(2) Uiso calc R 1 H
H4B 0.8545 0.2516 0.4649 0.043(2) Uiso calc R 1 H
H5A 0.6324 0.1281 0.4820 0.043(2) Uiso calc R 1 H
H5B 0.6845 0.3059 0.52286 0.043(2) Uiso calc R 1 H
H7A 0.4822 0.4267 0.3266 0.043(2) Uiso calc R 1 H
H7B 0.4772 0.4131 0.4262 0.043(2) Uiso calc R 1 H
H8A 0.4441 0.1034 0.4167 0.043(2) Uiso calc R 1 H
H8B 0.3541 0.1993 0.3507 0.043(2) Uiso calc R 1 H
H11A 0.3683 -0.3529 0.2010 0.043(2) Uiso calc R 1 H
H11B 0.4964 -0.2992 0.2234 0.043(2) Uiso calc R 1 H
H12A 0.4393 -0.2290 0.0749 0.043(2) Uiso calc R 1 H
H12B 0.3390 -0.1117 0.1004 0.043(2) Uiso calc R 1 H
H13A 0.5728 -0.0211 0.1416 0.043(2) Uiso calc R 1 H
H13B 0.4884 0.0825 0.0739 0.043(2) Uiso calc R 1 H
H14A 0.3892 0.1943 0.1844 0.043(2) Uiso calc R 1 H
H14B 0.5171 0.2456 0.2063 0.043(2) Uiso calc R 1 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
_geom_angle_publ_flag
C1 O1 C9 118.5(2) n
O2 C1 O1 123.1(2) n
O2 C1 C2 125.6(2) n
O1 C1 C2 111.3(2) n
C1 C2 C3 116.1(2) n
C2 C3 C4 115.6(2) n
C5 C4 C3 116.2(2) n
C6 C5 C4 115.1(2) n
O3 C6 C5 121.8(2) n
O3 C6 C7 121.0(2) n
C5 C6 C7 117.2(2) n
C6 C7 C8 115.7(2) n
C9 C8 C7 115.3(2) n
O1 C9 C8 109.8(2) n
O1 C9 C14 103.4(2) n
C8 C9 C14 114.0(2) n
O1 C9 C10 110.6(2) n
C8 C9 C10 112.3(2) n
C14 C9 C10 106.3(2) n
O4 C10 C11 122.9(2) n
O4 C10 C9 120.7(2) n
C11 C10 C9 115.5(2) n
C10 C11 C12 107.6(2) n
C13 C12 C11 110.7(2) n
C14 C13 C12 111.5(2) n
C13 C14 C9 112.6(2) n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.349(2) n
O1 C9 1.471(2) n
O2 C1 1.206(2) n
O3 C6 1.212(3) n
O4 C10 1.211(3) n
C1 C2 1.504(3) n
C2 C3 1.521(3) n
C3 C4 1.526(3) n
C4 C5 1.525(3) n
C5 C6 1.510(3) n
C6 C7 1.515(3) n
C7 C8 1.537(3) n
C8 C9 1.514(3) n
C9 C14 1.531(3) n
C9 C10 1.541(3) n
C10 C11 1.500(3) n
C11 C12 1.532(3) n
C12 C13 1.525(3) n
C13 C14 1.524(3) n
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
_geom_torsion_publ_flag
C9 O1 C1 O2 8.6(3) n
C9 O1 C1 C2 -173.2(2) n
O2 C1 C2 C3 -141.3(2) n
O1 C1 C2 C3 40.6(3) n
C1 C2 C3 C4 67.3(3) n
C2 C3 C4 C5 -60.5(3) n
C3 C4 C5 C6 -59.5(3) n
C4 C5 C6 O3 -24.5(3) n
C4 C5 C6 C7 158.5(2) n
O3 C6 C7 C8 121.0(2) n
C5 C6 C7 C8 -62.0(3) n
C6 C7 C8 C9 -54.8(3) n
C1 O1 C9 C8 73.1(2) n
C1 O1 C9 C14 -164.8(2) n
C1 O1 C9 C10 -51.4(2) n
C7 C8 C9 O1 61.8(2) n
C7 C8 C9 C14 -53.8(2) n
C7 C8 C9 C10 -174.8(2) n
O1 C9 C10 O4 137.3(2) n
C8 C9 C10 O4 14.3(3) n
C14 C9 C10 O4 -111.1(2) n
O1 C9 C10 C11 -53.5(2) n
C8 C9 C10 C11 -176.6(2) n
C14 C9 C10 C11 58.1(2) n
O4 C10 C11 C12 108.9(2) n
C9 C10 C11 C12 -60.0(2) n
C10 C11 C12 C13 56.6(2) n
C11 C12 C13 C14 -56.7(2) n
C12 C13 C14 C9 56.4(2) n
O1 C9 C14 C13 62.6(2) n
C8 C9 C14 C13 -178.1(2) n
C10 C9 C14 C13 -53.9(2) n