#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2007281.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_2007281
loop_
_publ_author_name
'Branco, M. C.'
'Rodrigues, A. M. Goncalves D.'
'do Gambardella, M. T.'
'Muzzi, R. M.'
'Ferraz, H. M. C.'
_publ_section_title
;
 \D^4^-7,7-Ethylenedioxy-10-methyloctal-1-one
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              664
_journal_page_last               666
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C13 H18 O3'
_chemical_formula_sum            'C13 H18 O3'
_chemical_formula_weight         222.27
_chemical_name_systematic
;
\D^4^-7,7-ethylenedioxy-10-methyl-octal-1-one
;
_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'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 100.142(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.3409(10)
_cell_length_b                   5.8353(5)
_cell_length_c                   15.0408(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.20
_cell_measurement_theta_min      9.60
_cell_volume                     1152.60(15)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'MolEN (Fair, 1990)'
_computing_molecular_graphics    'ZORTEP and XPMA (Zsolnai, 1994)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       \w/2\q
_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  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0676
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            2435
_diffrn_reflns_theta_max         26.29
_diffrn_reflns_theta_min         3.75
_diffrn_standards_decay_%        3.1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       thin_plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.277
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.023
_refine_ls_goodness_of_fit_obs   1.120
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2330
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_restrained_S_obs      1.120
_refine_ls_R_factor_all          0.1224
_refine_ls_R_factor_obs          0.0530
_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^)+(0.0886P)^2^+0.2067P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1737
_refine_ls_wR_factor_obs         0.1389
_reflns_number_observed          1303
_reflns_number_total             2330
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    sx1036.cif
_[local]_cod_data_source_block   sx1036
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
_cod_original_cell_volume        1152.6(2)
_cod_database_code               2007281
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 0.0593(14) 0.154(3) 0.081(2) 0.041(2) 0.0171(12) 0.013(2)
O2 0.0409(10) 0.0489(12) 0.0709(13) 0.0062(9) -0.0041(9) 0.0057(10)
O3 0.0485(11) 0.0388(11) 0.0611(12) 0.0002(9) -0.0088(8) 0.0003(9)
C1 0.0375(13) 0.0368(14) 0.0414(13) -0.0005(11) 0.0039(10) -0.0077(11)
C2 0.042(2) 0.063(2) 0.056(2) 0.0044(14) 0.0040(13) -0.0123(14)
C3 0.059(2) 0.089(3) 0.057(2) 0.012(2) -0.0193(14) -0.017(2)
C4 0.084(2) 0.054(2) 0.045(2) 0.008(2) -0.0117(15) -0.0070(13)
C5 0.068(2) 0.053(2) 0.0386(14) -0.0031(15) 0.0116(12) -0.0057(13)
C6 0.0449(14) 0.0400(15) 0.0352(13) 0.0035(11) 0.0080(10) -0.0090(11)
C7 0.0439(15) 0.053(2) 0.0450(15) 0.0019(13) 0.0133(12) -0.0041(13)
C8 0.0362(13) 0.0346(14) 0.0475(14) 0.0067(11) -0.0002(10) -0.0016(11)
C9 0.045(2) 0.062(2) 0.068(2) -0.0099(14) 0.0001(13) 0.0155(15)
C10 0.052(2) 0.054(2) 0.054(2) -0.0117(14) -0.0055(13) 0.0032(14)
C11 0.0516(15) 0.046(2) 0.0347(12) 0.0086(13) 0.0035(11) 0.0037(12)
C12 0.0420(14) 0.046(2) 0.0391(13) -0.0007(12) 0.0106(10) -0.0005(11)
C13 0.059(2) 0.039(2) 0.085(2) -0.0046(14) 0.006(2) -0.0116(15)
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 -0.1936(2) -0.1305(6) 0.8185(2) 0.0974(10) Uani d . 1 O
O2 0.28923(13) -0.2190(3) 0.93007(13) 0.0553(6) Uani d . 1 O
O3 0.18782(13) 0.0925(3) 0.89147(12) 0.0517(5) Uani d . 1 O
C1 -0.0264(2) -0.2658(4) 0.8094(2) 0.0389(6) Uani d . 1 C
C2 -0.1312(2) -0.1679(5) 0.7712(2) 0.0543(7) Uani d . 1 C
C3 -0.1569(2) -0.1543(6) 0.6696(2) 0.0721(10) Uani d . 1 C
H3A -0.1601(2) -0.3078(6) 0.6445(2) 0.086 Uiso calc R 1 H
H3B -0.2234(2) -0.0841(6) 0.6520(2) 0.086 Uiso calc R 1 H
C4 -0.0787(2) -0.0163(5) 0.6318(2) 0.0640(9) Uani d . 1 C
H4A -0.0845(2) -0.0495(5) 0.5679(2) 0.077 Uiso calc R 1 H
H4B -0.0926(2) 0.1455(5) 0.6380(2) 0.077 Uiso calc R 1 H
C5 0.0270(2) -0.0661(5) 0.6780(2) 0.0527(7) Uani d . 1 C
H5 0.0800(2) -0.0113(5) 0.6512(2) 0.063 Uiso calc R 1 H
C6 0.0515(2) -0.1825(4) 0.7545(2) 0.0399(6) Uani d . 1 C
C7 0.1606(2) -0.2350(5) 0.7948(2) 0.0467(7) Uani d . 1 C
H7A 0.2052(2) -0.1624(5) 0.7588(2) 0.056 Uiso calc R 1 H
H7B 0.1716(2) -0.3992(5) 0.7932(2) 0.056 Uiso calc R 1 H
C8 0.1879(2) -0.1515(4) 0.8917(2) 0.0403(6) Uani d . 1 C
C9 0.3486(2) -0.0182(5) 0.9494(2) 0.0594(8) Uani d . 1 C
H9A 0.3856(2) 0.0165(5) 0.9010(2) 0.071 Uiso calc R 1 H
H9B 0.3968(2) -0.0344(5) 1.0054(2) 0.071 Uiso calc R 1 H
C10 0.2714(2) 0.1637(5) 0.9574(2) 0.0553(8) Uani d . 1 C
H10A 0.2539(2) 0.1660(5) 1.0173(2) 0.066 Uiso calc R 1 H
H10B 0.2955(2) 0.3141(5) 0.9435(2) 0.066 Uiso calc R 1 H
C11 0.1146(2) -0.2443(5) 0.9489(2) 0.0446(6) Uani d . 1 C
H11A 0.1309(2) -0.1802(5) 1.0093(2) 0.054 Uiso calc R 1 H
H11B 0.1217(2) -0.4094(5) 0.9538(2) 0.054 Uiso calc R 1 H
C12 0.0053(2) -0.1842(5) 0.9077(2) 0.0420(6) Uani d . 1 C
H12A -0.0030(2) -0.0193(5) 0.9096(2) 0.050 Uiso calc R 1 H
H12B -0.0400(2) -0.2524(5) 0.9441(2) 0.050 Uiso calc R 1 H
C13 -0.0355(2) -0.5293(5) 0.8064(2) 0.0616(8) Uani d . 1 C
H13A -0.0802(12) -0.5783(5) 0.8463(10) 0.092 Uiso calc R 1 H
H13B 0.0306(3) -0.5962(5) 0.8253(13) 0.092 Uiso calc R 1 H
H13C -0.0625(14) -0.5774(5) 0.7459(3) 0.092 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
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
5 1 3
-3 2 4
-2 -2 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
C9 O2 C8 108.1(2) y
C10 O3 C8 106.9(2) y
C6 C1 C2 110.2(2) y
C6 C1 C12 109.0(2) y
C2 C1 C12 108.9(2) y
C6 C1 C13 111.2(2) y
C2 C1 C13 107.5(2) y
C12 C1 C13 110.0(2) y
O1 C2 C3 122.0(3) y
O1 C2 C1 121.9(3) y
C3 C2 C1 115.5(2) y
C4 C3 C2 111.1(2) y
C5 C4 C3 112.5(3) y
C6 C5 C4 125.0(3) y
C5 C6 C7 121.8(2) y
C5 C6 C1 123.2(2) y
C7 C6 C1 115.0(2) y
C6 C7 C8 111.8(2) y
O3 C8 O2 106.1(2) y
O3 C8 C11 111.1(2) y
O2 C8 C11 109.4(2) y
O3 C8 C7 108.6(2) y
O2 C8 C7 110.4(2) y
C11 C8 C7 111.2(2) y
O2 C9 C10 103.6(2) y
O3 C10 C9 101.8(2) y
C8 C11 C12 110.8(2) y
C11 C12 C1 113.7(2) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 1.206(3) y
O2 C9 1.416(3) y
O2 C8 1.429(3) y
O3 C10 1.417(3) y
O3 C8 1.424(3) y
C1 C6 1.517(3) y
C1 C2 1.525(4) y
C1 C12 1.540(3) y
C1 C13 1.542(4) y
C2 C3 1.509(4) y
C3 C4 1.506(5) y
C4 C5 1.486(4) y
C5 C6 1.327(4) y
C6 C7 1.507(3) y
C7 C8 1.519(3) y
C8 C11 1.511(3) y
C9 C10 1.499(4) y
C11 C12 1.522(3) y
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
C6 C1 C2 O1 -150.1(3) ?
C12 C1 C2 O1 -30.6(4) ?
C13 C1 C2 O1 88.5(4) ?
C6 C1 C2 C3 38.6(3) ?
C12 C1 C2 C3 158.1(2) n
C13 C1 C2 C3 -82.7(3) ?
O1 C2 C3 C4 132.1(3) ?
C1 C2 C3 C4 -56.6(4) ?
C2 C3 C4 C5 41.1(4) ?
C3 C4 C5 C6 -12.4(4) ?
C4 C5 C6 C7 177.1(3) n
C4 C5 C6 C1 -4.9(4) n
C2 C1 C6 C5 -8.0(3) ?
C12 C1 C6 C5 -127.4(3) ?
C13 C1 C6 C5 111.1(3) ?
C2 C1 C6 C7 170.1(2) ?
C12 C1 C6 C7 50.7(3) ?
C13 C1 C6 C7 -70.8(3) ?
C5 C6 C7 C8 125.0(3) n
C1 C6 C7 C8 -53.1(3) ?
C10 O3 C8 O2 -21.7(3) ?
C10 O3 C8 C11 97.1(2) n
C10 O3 C8 C7 -140.3(2) n
C9 O2 C8 O3 -1.8(3) ?
C9 O2 C8 C11 -121.7(2) n
C9 O2 C8 C7 115.6(2) n
C6 C7 C8 O3 -68.5(3) n
C6 C7 C8 O2 175.7(2) n
C6 C7 C8 C11 54.0(3) ?
C8 O2 C9 C10 22.9(3) ?
C8 O3 C10 C9 35.0(3) ?
O2 C9 C10 O3 -35.2(3) ?
O3 C8 C11 C12 65.7(3) n
O2 C8 C11 C12 -177.5(2) n
C7 C8 C11 C12 -55.3(3) ?
C8 C11 C12 C1 55.7(3) ?
C6 C1 C12 C11 -51.9(3) ?
C2 C1 C12 C11 -172.2(2) n
C13 C1 C12 C11 70.2(3) ?