#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:52:38 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301791 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/72/2007281.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, Marcelo Cardoso'
'Rodrigues, Ana Maria Goncalves D.'
'Gambardella, Maria Teresa do P.'
'Muzzi, Rosana M.'
'Ferraz, Helena 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_paper_doi               10.1107/S0108270197019173
_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      ?
_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          .0530
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0886P)^2^+0.2067P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1737
_refine_ls_wR_factor_obs         .1389
_reflns_number_observed          1303
_reflns_number_total             2330
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            sx1036.cif
_cod_data_source_block           sx1036
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0886P)^2^+0.2067P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0886P)^2^+0.2067P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1152.6(2)
_cod_original_sg_symbol_H-M      'P 21/n'
_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 .0593(14) .154(3) .081(2) .041(2) .0171(12) .013(2)
O2 .0409(10) .0489(12) .0709(13) .0062(9) -.0041(9) .0057(10)
O3 .0485(11) .0388(11) .0611(12) .0002(9) -.0088(8) .0003(9)
C1 .0375(13) .0368(14) .0414(13) -.0005(11) .0039(10) -.0077(11)
C2 .042(2) .063(2) .056(2) .0044(14) .0040(13) -.0123(14)
C3 .059(2) .089(3) .057(2) .012(2) -.0193(14) -.017(2)
C4 .084(2) .054(2) .045(2) .008(2) -.0117(15) -.0070(13)
C5 .068(2) .053(2) .0386(14) -.0031(15) .0116(12) -.0057(13)
C6 .0449(14) .0400(15) .0352(13) .0035(11) .0080(10) -.0090(11)
C7 .0439(15) .053(2) .0450(15) .0019(13) .0133(12) -.0041(13)
C8 .0362(13) .0346(14) .0475(14) .0067(11) -.0002(10) -.0016(11)
C9 .045(2) .062(2) .068(2) -.0099(14) .0001(13) .0155(15)
C10 .052(2) .054(2) .054(2) -.0117(14) -.0055(13) .0032(14)
C11 .0516(15) .046(2) .0347(12) .0086(13) .0035(11) .0037(12)
C12 .0420(14) .046(2) .0391(13) -.0007(12) .0106(10) -.0005(11)
C13 .059(2) .039(2) .085(2) -.0046(14) .006(2) -.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_disorder_group
_atom_site_type_symbol
O1 -.1936(2) -.1305(6) .8185(2) .0974(10) Uani d . 1 . O
O2 .28923(13) -.2190(3) .93007(13) .0553(6) Uani d . 1 . O
O3 .18782(13) .0925(3) .89147(12) .0517(5) Uani d . 1 . O
C1 -.0264(2) -.2658(4) .8094(2) .0389(6) Uani d . 1 . C
C2 -.1312(2) -.1679(5) .7712(2) .0543(7) Uani d . 1 . C
C3 -.1569(2) -.1543(6) .6696(2) .0721(10) Uani d . 1 . C
H3A -.1601(2) -.3078(6) .6445(2) .086 Uiso calc R 1 . H
H3B -.2234(2) -.0841(6) .6520(2) .086 Uiso calc R 1 . H
C4 -.0787(2) -.0163(5) .6318(2) .0640(9) Uani d . 1 . C
H4A -.0845(2) -.0495(5) .5679(2) .077 Uiso calc R 1 . H
H4B -.0926(2) .1455(5) .6380(2) .077 Uiso calc R 1 . H
C5 .0270(2) -.0661(5) .6780(2) .0527(7) Uani d . 1 . C
H5 .0800(2) -.0113(5) .6512(2) .063 Uiso calc R 1 . H
C6 .0515(2) -.1825(4) .7545(2) .0399(6) Uani d . 1 . C
C7 .1606(2) -.2350(5) .7948(2) .0467(7) Uani d . 1 . C
H7A .2052(2) -.1624(5) .7588(2) .056 Uiso calc R 1 . H
H7B .1716(2) -.3992(5) .7932(2) .056 Uiso calc R 1 . H
C8 .1879(2) -.1515(4) .8917(2) .0403(6) Uani d . 1 . C
C9 .3486(2) -.0182(5) .9494(2) .0594(8) Uani d . 1 . C
H9A .3856(2) .0165(5) .9010(2) .071 Uiso calc R 1 . H
H9B .3968(2) -.0344(5) 1.0054(2) .071 Uiso calc R 1 . H
C10 .2714(2) .1637(5) .9574(2) .0553(8) Uani d . 1 . C
H10A .2539(2) .1660(5) 1.0173(2) .066 Uiso calc R 1 . H
H10B .2955(2) .3141(5) .9435(2) .066 Uiso calc R 1 . H
C11 .1146(2) -.2443(5) .9489(2) .0446(6) Uani d . 1 . C
H11A .1309(2) -.1802(5) 1.0093(2) .054 Uiso calc R 1 . H
H11B .1217(2) -.4094(5) .9538(2) .054 Uiso calc R 1 . H
C12 .0053(2) -.1842(5) .9077(2) .0420(6) Uani d . 1 . C
H12A -.0030(2) -.0193(5) .9096(2) .050 Uiso calc R 1 . H
H12B -.0400(2) -.2524(5) .9441(2) .050 Uiso calc R 1 . H
C13 -.0355(2) -.5293(5) .8064(2) .0616(8) Uani d . 1 . C
H13A -.0802(12) -.5783(5) .8463(10) .092 Uiso calc R 1 . H
H13B .0306(3) -.5962(5) .8253(13) .092 Uiso calc R 1 . H
H13C -.0625(14) -.5774(5) .7459(3) .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_site_symmetry_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) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 11183650
