#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/42/2234222.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_2234222
loop_
_publ_author_name
'Asiri, Abdullah M.'
'Faidallah, Hassan M.'
'Al-Nemari, Khulud F.'
'Ng, Seik Weng'
'Tiekink, Edward R. T.'
_publ_section_title
;
 (2E)-2-[(2H-1,3-Benzodioxol-5-yl)methylidene]-2,3-dihydro-1H-inden-1-one
;
_journal_coeditor_code           HB6667
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1015
_journal_paper_doi               10.1107/S1600536812009464
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C17 H12 O3'
_chemical_formula_moiety         'C17 H12 O3'
_chemical_formula_sum            'C17 H12 O3'
_chemical_formula_weight         264.27
_chemical_name_systematic
;
(2E)-2-[(2H-1,3-Benzodioxol-5-yl)methylidene]-2,3-dihydro-
1H-inden-1-one
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.6102(12)
_cell_length_b                   7.3497(10)
_cell_length_c                   26.569(4)
_cell_measurement_reflns_used    930
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5019
_cell_measurement_theta_min      2.8048
_cell_volume                     2462.4(6)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
'Agilent SuperNova Dual diffractometer with an Atlas detector'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_sigmaI/netI    0.0832
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            6424
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         3.23
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9951
_exptl_absorpt_correction_T_min  0.9666
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2011)'
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.258
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2820
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.0553
_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)+(0.0502P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1355
_reflns_number_gt                1697
_reflns_number_total             2820
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6667.cif
_cod_data_source_block           I
_cod_original_cell_volume        2462.5(5)
_cod_database_code               2234222
_cod_database_fobs_code          2234222
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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 0.92949(12) 0.5693(2) 0.65488(6) 0.0275(4) Uani d . 1 1
O O2 0.61242(12) 0.2489(2) 0.41852(5) 0.0283(4) Uani d . 1 1
O O3 0.75515(12) 0.1445(2) 0.37080(6) 0.0283(4) Uani d . 1 1
C C1 0.83441(19) 0.5422(3) 0.64704(8) 0.0212(5) Uani d . 1 1
C C2 0.74657(18) 0.5690(3) 0.68310(8) 0.0197(5) Uani d . 1 1
C C3 0.75035(19) 0.6274(3) 0.73287(8) 0.0231(5) Uani d . 1 1
H H3 0.8154 0.6647 0.7476 0.028 Uiso calc R 1 1
C C4 0.65715(19) 0.6298(3) 0.76036(8) 0.0267(6) Uani d . 1 1
H H4 0.6578 0.6709 0.7943 0.032 Uiso calc R 1 1
C C5 0.5625(2) 0.5723(3) 0.73861(9) 0.0291(6) Uani d . 1 1
H H5 0.4996 0.5711 0.7583 0.035 Uiso calc R 1 1
C C6 0.55825(19) 0.5165(3) 0.68870(8) 0.0263(6) Uani d . 1 1
H H6 0.4931 0.4781 0.6742 0.032 Uiso calc R 1 1
C C7 0.65094(18) 0.5179(3) 0.66035(8) 0.0210(5) Uani d . 1 1
C C8 0.66690(17) 0.4682(3) 0.60554(8) 0.0200(5) Uani d . 1 1
H H8A 0.6391 0.3449 0.5983 0.024 Uiso calc R 1 1
H H8B 0.6314 0.5569 0.5831 0.024 Uiso calc R 1 1
C C9 0.78635(18) 0.4750(3) 0.59906(8) 0.0199(5) Uani d . 1 1
C C10 0.84909(18) 0.4281(3) 0.56046(8) 0.0207(5) Uani d . 1 1
H H10 0.9227 0.4445 0.5665 0.025 Uiso calc R 1 1
C C11 0.82372(18) 0.3562(3) 0.51066(8) 0.0194(5) Uani d . 1 1
C C12 0.90839(19) 0.2975(3) 0.48054(8) 0.0254(5) Uani d . 1 1
H H12 0.9785 0.3069 0.4934 0.030 Uiso calc R 1 1
C C13 0.89343(19) 0.2255(3) 0.43228(8) 0.0266(5) Uani d . 1 1
H H13 0.9514 0.1870 0.4121 0.032 Uiso calc R 1 1
C C14 0.79071(19) 0.2135(3) 0.41575(8) 0.0221(5) Uani d . 1 1
C C15 0.70630(17) 0.2729(3) 0.44464(8) 0.0197(5) Uani d . 1 1
C C16 0.71892(18) 0.3447(3) 0.49167(8) 0.0210(5) Uani d . 1 1
H H16 0.6599 0.3851 0.5109 0.025 Uiso calc R 1 1
C C17 0.64264(19) 0.1752(4) 0.37035(8) 0.0296(6) Uani d . 1 1
H H17A 0.6048 0.0593 0.3642 0.036 Uiso calc R 1 1
H H17B 0.6239 0.2616 0.3432 0.036 Uiso calc R 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
C15 O2 C17 105.49(17)
C14 O3 C17 105.78(16)
O1 C1 C2 126.7(2)
O1 C1 C9 126.3(2)
C2 C1 C9 107.04(19)
C3 C2 C7 121.5(2)
C3 C2 C1 129.2(2)
C7 C2 C1 109.26(19)
C4 C3 C2 118.5(2)
C4 C3 H3 120.8
C2 C3 H3 120.8
C3 C4 C5 120.3(2)
C3 C4 H4 119.8
C5 C4 H4 119.8
C6 C5 C4 121.3(2)
C6 C5 H5 119.4
C4 C5 H5 119.4
C7 C6 C5 118.9(2)
C7 C6 H6 120.6
C5 C6 H6 120.6
C6 C7 C2 119.5(2)
C6 C7 C8 129.1(2)
C2 C7 C8 111.42(19)
C9 C8 C7 103.49(17)
C9 C8 H8A 111.1
C7 C8 H8A 111.1
C9 C8 H8B 111.1
C7 C8 H8B 111.1
H8A C8 H8B 109.0
C10 C9 C1 119.9(2)
C10 C9 C8 131.7(2)
C1 C9 C8 108.44(18)
C9 C10 C11 131.1(2)
C9 C10 H10 114.5
C11 C10 H10 114.5
C12 C11 C16 119.2(2)
C12 C11 C10 117.5(2)
C16 C11 C10 123.3(2)
C13 C12 C11 122.4(2)
C13 C12 H12 118.8
C11 C12 H12 118.8
C14 C13 C12 116.4(2)
C14 C13 H13 121.8
C12 C13 H13 121.8
C13 C14 O3 127.7(2)
C13 C14 C15 121.9(2)
O3 C14 C15 110.4(2)
C16 C15 C14 122.7(2)
C16 C15 O2 127.4(2)
C14 C15 O2 109.86(19)
C15 C16 C11 117.2(2)
C15 C16 H16 121.4
C11 C16 H16 121.4
O3 C17 O2 108.22(17)
O3 C17 H17A 110.1
O2 C17 H17A 110.1
O3 C17 H17B 110.1
O2 C17 H17B 110.1
H17A C17 H17B 108.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.233(3)
O2 C15 1.384(3)
O2 C17 1.441(3)
O3 C14 1.373(3)
O3 C17 1.437(3)
C1 C2 1.478(3)
C1 C9 1.496(3)
C2 C3 1.391(3)
C2 C7 1.400(3)
C3 C4 1.384(3)
C3 H3 0.9500
C4 C5 1.392(3)
C4 H4 0.9500
C5 C6 1.389(3)
C5 H5 0.9500
C6 C7 1.391(3)
C6 H6 0.9500
C7 C8 1.515(3)
C8 C9 1.517(3)
C8 H8A 0.9900
C8 H8B 0.9900
C9 C10 1.340(3)
C10 C11 1.460(3)
C10 H10 0.9500
C11 C12 1.402(3)
C11 C16 1.417(3)
C12 C13 1.400(3)
C12 H12 0.9500
C13 C14 1.371(3)
C13 H13 0.9500
C14 C15 1.383(3)
C15 C16 1.366(3)
C16 H16 0.9500
C17 H17A 0.9900
C17 H17B 0.9900
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
C5 H5 O1 6_557 0.95 2.47 3.290(3) 144
C17 H17A O1 4_456 0.99 2.46 3.302(3) 143
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
O1 C1 C2 C3 -0.8(4)
C9 C1 C2 C3 179.0(2)
O1 C1 C2 C7 -178.2(2)
C9 C1 C2 C7 1.6(2)
C7 C2 C3 C4 1.6(3)
C1 C2 C3 C4 -175.5(2)
C2 C3 C4 C5 1.0(3)
C3 C4 C5 C6 -2.0(4)
C4 C5 C6 C7 0.3(3)
C5 C6 C7 C2 2.2(3)
C5 C6 C7 C8 -178.5(2)
C3 C2 C7 C6 -3.2(3)
C1 C2 C7 C6 174.43(19)
C3 C2 C7 C8 177.4(2)
C1 C2 C7 C8 -5.0(2)
C6 C7 C8 C9 -173.2(2)
C2 C7 C8 C9 6.1(2)
O1 C1 C9 C10 3.9(3)
C2 C1 C9 C10 -175.9(2)
O1 C1 C9 C8 -177.9(2)
C2 C1 C9 C8 2.3(2)
C7 C8 C9 C10 172.9(2)
C7 C8 C9 C1 -4.9(2)
C1 C9 C10 C11 178.6(2)
C8 C9 C10 C11 1.0(4)
C9 C10 C11 C12 -171.8(2)
C9 C10 C11 C16 8.7(4)
C16 C11 C12 C13 -0.7(3)
C10 C11 C12 C13 179.7(2)
C11 C12 C13 C14 -0.5(3)
C12 C13 C14 O3 -178.3(2)
C12 C13 C14 C15 1.4(3)
C17 O3 C14 C13 -175.9(2)
C17 O3 C14 C15 4.3(2)
C13 C14 C15 C16 -1.1(4)
O3 C14 C15 C16 178.7(2)
C13 C14 C15 O2 178.5(2)
O3 C14 C15 O2 -1.7(3)
C17 O2 C15 C16 177.9(2)
C17 O2 C15 C14 -1.7(2)
C14 C15 C16 C11 -0.2(3)
O2 C15 C16 C11 -179.78(19)
C12 C11 C16 C15 1.1(3)
C10 C11 C16 C15 -179.4(2)
C14 O3 C17 O2 -5.3(2)
C15 O2 C17 O3 4.3(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4949635
