#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/38/2233839.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_2233839
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Quah, Ching Kheng'
'Attia, Mohamed I.'
'El-Behairy, Mohammed F.'
'Al-Deeb, Omar A.'
_publ_section_title
;
 (E)-1-(1,3-Benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-one
;
_journal_coeditor_code           HB6621
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o634
_journal_paper_doi               10.1107/S1600536812004242
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C14 H16 O3'
_chemical_formula_moiety         'C14 H16 O3'
_chemical_formula_sum            'C14 H16 O3'
_chemical_formula_weight         232.27
_chemical_name_systematic
;
(E)-1-(1,3-Benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-one
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.6760(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.53050(10)
_cell_length_b                   6.67980(10)
_cell_length_c                   13.7264(2)
_cell_measurement_reflns_used    4988
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      32.74
_cell_measurement_theta_min      2.99
_cell_volume                     594.719(15)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_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  0.0177
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8645
_diffrn_reflns_theta_full        32.74
_diffrn_reflns_theta_max         32.74
_diffrn_reflns_theta_min         2.99
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9778
_exptl_absorpt_correction_T_min  0.9630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.421
_exptl_crystal_size_mid          0.315
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.282
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2336
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0370
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0687P)²+0.0862P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1103
_reflns_number_gt                2117
_reflns_number_total             2336
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6621.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2233839
_cod_database_fobs_code          2233839
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
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_symmetry_multiplicity
O O1 -0.08309(10) 0.7500 0.73220(5) 0.01756(15) Uani d S 1 2
O O2 0.23387(11) 0.7500 0.67099(5) 0.02109(16) Uani d S 1 2
O O3 -0.10343(12) 0.7500 0.11962(5) 0.0284(2) Uani d S 1 2
C C1 -0.27995(14) 0.7500 0.46990(7) 0.01734(18) Uani d S 1 2
C C2 -0.29527(14) 0.7500 0.57113(7) 0.01815(18) Uani d S 1 2
C C3 -0.11215(14) 0.7500 0.63184(6) 0.01431(16) Uani d S 1 2
C C4 0.13580(14) 0.7500 0.75950(6) 0.01731(17) Uani d S 1 2
C C5 0.07776(13) 0.7500 0.59505(6) 0.01401(16) Uani d S 1 2
C C6 0.09473(13) 0.7500 0.49674(6) 0.01446(16) Uani d S 1 2
C C7 -0.08980(13) 0.7500 0.43188(6) 0.01338(16) Uani d S 1 2
C C8 -0.08717(14) 0.7500 0.32577(6) 0.01474(16) Uani d S 1 2
C C9 0.08137(14) 0.7500 0.27781(6) 0.01558(17) Uani d S 1 2
C C10 0.06467(14) 0.7500 0.16901(6) 0.01549(17) Uani d S 1 2
C C11 0.26558(13) 0.7500 0.12174(6) 0.01458(16) Uani d S 1 2
C C12 0.21897(17) 0.7500 0.01018(7) 0.0271(2) Uani d S 1 2
C C13 0.39093(12) 0.56198(11) 0.15410(6) 0.02431(16) Uani d . 1 1
H H1A -0.406(3) 0.7500 0.4256(12) 0.032(4) Uiso d S 1 2
H H2A -0.424(3) 0.7500 0.5974(12) 0.031(4) Uiso d S 1 2
H H4A 0.1728(15) 0.6272(15) 0.7976(7) 0.018(2) Uiso d . 1 1
H H6A 0.239(2) 0.7500 0.4738(11) 0.025(4) Uiso d S 1 2
H H8A -0.220(3) 0.7500 0.2883(12) 0.034(4) Uiso d S 1 2
H H9A 0.218(3) 0.7500 0.3117(12) 0.032(4) Uiso d S 1 2
H H12A 0.138(2) 0.631(2) -0.0117(9) 0.041(3) Uiso d . 1 1
H H12B 0.350(3) 0.7500 -0.0180(12) 0.030(4) Uiso d S 1 2
H H13A 0.4241(18) 0.5522(18) 0.2246(9) 0.034(3) Uiso d . 1 1
H H13B 0.3154(19) 0.4437(18) 0.1331(8) 0.033(3) Uiso d . 1 1
H H13C 0.5215(17) 0.5639(16) 0.1247(8) 0.026(3) Uiso d . 1 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'
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
C3 O1 C4 . . 106.27(6)
C5 O2 C4 . . 106.12(7)
C7 C1 C2 . . 122.43(8)
C7 C1 H1A . . 119.6(10)
C2 C1 H1A . . 117.9(10)
C3 C2 C1 . . 116.25(8)
C3 C2 H2A . . 120.9(10)
C1 C2 H2A . . 122.9(10)
O1 C3 C2 . . 128.23(8)
O1 C3 C5 . . 109.87(8)
C2 C3 C5 . . 121.90(8)
O1 C4 O2 . . 107.90(7)
O1 C4 H4A . . 108.2(6)
O2 C4 H4A . . 110.0(6)
C6 C5 O2 . . 127.76(8)
C6 C5 C3 . . 122.41(8)
O2 C5 C3 . . 109.83(7)
C5 C6 C7 . . 117.46(8)
C5 C6 H6A . . 119.0(9)
C7 C6 H6A . . 123.5(9)
C1 C7 C6 . . 119.55(8)
C1 C7 C8 . . 119.05(8)
C6 C7 C8 . . 121.41(7)
C9 C8 C7 . . 126.39(8)
C9 C8 H8A . . 118.6(10)
C7 C8 H8A . . 115.0(10)
C8 C9 C10 . . 121.54(8)
C8 C9 H9A . . 122.2(10)
C10 C9 H9A . . 116.3(10)
O3 C10 C9 . . 120.97(8)
O3 C10 C11 . . 121.63(8)
C9 C10 C11 . . 117.40(7)
C12 C11 C10 . . 110.16(8)
C12 C11 C13 . 4_575 109.12(5)
C10 C11 C13 . 4_575 109.38(5)
C12 C11 C13 . . 109.12(5)
C10 C11 C13 . . 109.38(5)
C13 C11 C13 4_575 . 109.67(8)
C11 C12 H12A . . 110.1(7)
C11 C12 H12B . . 108.4(10)
H12A C12 H12B . . 110.1(9)
C11 C13 H13A . . 113.2(7)
C11 C13 H13B . . 110.4(7)
H13A C13 H13B . . 107.0(10)
C11 C13 H13C . . 109.2(6)
H13A C13 H13C . . 107.8(9)
H13B C13 H13C . . 109.1(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C3 . 1.3685(10)
O1 C4 . 1.4350(11)
O2 C5 . 1.3706(11)
O2 C4 . 1.4378(11)
O3 C10 . 1.2214(11)
C1 C7 . 1.4018(12)
C1 C2 . 1.4046(12)
C1 H1A . 0.967(17)
C2 C3 . 1.3758(13)
C2 H2A . 0.952(17)
C3 C5 . 1.3924(11)
C4 H4A . 0.988(10)
C5 C6 . 1.3668(11)
C6 C7 . 1.4125(12)
C6 H6A . 1.026(16)
C7 C8 . 1.4587(12)
C8 C9 . 1.3465(12)
C8 H8A . 0.956(18)
C9 C10 . 1.4848(12)
C9 H9A . 0.960(17)
C10 C11 . 1.5298(12)
C11 C12 . 1.5262(13)
C11 C13 4_575 1.5363(9)
C11 C13 . 1.5363(9)
C12 H12A . 0.985(13)
C12 H12B . 0.980(17)
C13 H13A . 0.969(12)
C13 H13B . 0.958(12)
C13 H13C . 0.985(11)
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
_geom_hbond_publ_flag
C2 H2A O2 1_455 0.953(19) 2.557(19) 3.5092(12) 179.0(14) yes
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_4
_geom_torsion
C7 C1 C2 C3 . 0.0
C4 O1 C3 C2 . 180.0
C4 O1 C3 C5 . 0.0
C1 C2 C3 O1 . 180.0
C1 C2 C3 C5 . 0.0
C3 O1 C4 O2 . 0.0
C5 O2 C4 O1 . 0.0
C4 O2 C5 C6 . 180.0
C4 O2 C5 C3 . 0.0
O1 C3 C5 C6 . 180.0
C2 C3 C5 C6 . 0.0
O1 C3 C5 O2 . 0.0
C2 C3 C5 O2 . 180.0
O2 C5 C6 C7 . 180.0
C3 C5 C6 C7 . 0.0
C2 C1 C7 C6 . 0.0
C2 C1 C7 C8 . 180.0
C5 C6 C7 C1 . 0.0
C5 C6 C7 C8 . 180.0
C1 C7 C8 C9 . 180.0
C6 C7 C8 C9 . 0.0
C7 C8 C9 C10 . 180.0
C8 C9 C10 O3 . 0.0
C8 C9 C10 C11 . 180.0
O3 C10 C11 C12 . 0.0
C9 C10 C11 C12 . 180.0
O3 C10 C11 C13 4_575 119.93(5)
C9 C10 C11 C13 4_575 -60.07(5)
O3 C10 C11 C13 . -119.93(5)
C9 C10 C11 C13 . 60.07(5)
