#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/34/2223429.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_2223429
loop_
_publ_author_name
'Loghmani-Khouzani, Hossein'
'Abdul Rahman, Noorsaadah'
'Robinson, Ward T.'
'Yaeghoobi, Marzieh'
'Kia, Reza'
_publ_section_title
(E)-3-(6-Nitrobenzo[d][1,3]dioxol-5-yl)-1-(2,4,6-trimethoxyphenyl)prop-2-en-1-one
_journal_coeditor_code           HK2765
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2545
_journal_paper_doi               10.1107/S1600536809036435
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C19 H17 N O8'
_chemical_formula_moiety         'C19 H17 N O8'
_chemical_formula_sum            'C19 H17 N O8'
_chemical_formula_weight         387.34
_chemical_melting_point          497
_chemical_name_common
;
(E)-3-(6-Nitrobenzo[d][1,3]dioxol-5-yl)-1-(2,4,6-
trimethoxy)prop-2-en-1-one
;
_chemical_name_systematic
;
(E)-3-(6-Nitrobenzo[d][1,3]dioxol-5-yl)-1-(2,4,6-
trimethoxyphenyl) prop-2-en-1-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.1120(10)
_cell_angle_beta                 103.9590(10)
_cell_angle_gamma                105.3840(10)
_cell_formula_units_Z            2
_cell_length_a                   7.30440(10)
_cell_length_b                   10.12640(10)
_cell_length_c                   12.8600(2)
_cell_measurement_reflns_used    3206
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      32.5
_cell_measurement_theta_min      2.45
_cell_volume                     882.91(2)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector diffractometer
;
_diffrn_measurement_method       'φ and ω scans'
_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  0.0126
_diffrn_reflns_av_sigmaI/netI    0.0221
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4805
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.10
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.9886
_exptl_absorpt_correction_T_min  0.9729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.218
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3038
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0319
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0394P)²+0.3499P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0829
_reflns_number_gt                2733
_reflns_number_total             3038
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2765.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '497 K' was changed to '497' - the
value should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '497 K' was changed to '497' - the
value should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2223429
_cod_database_fobs_code          2223429
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_disorder_assembly
_atom_site_disorder_group
O O1 0.15752(13) 0.44029(9) 0.12868(7) 0.0209(2) Uani d . 1 . .
O O2 0.54955(19) 1.20445(11) 0.27950(9) 0.0430(3) Uani d . 1 . .
O O3 0.37219(16) 1.00784(10) 0.30427(8) 0.0309(3) Uani d . 1 . .
O O4 0.11057(18) 1.00352(10) -0.19561(8) 0.0355(3) Uani d . 1 . .
O O5 0.21032(16) 1.22795(10) -0.11005(8) 0.0298(3) Uani d . 1 . .
O O6 0.58160(13) 0.48499(9) 0.17340(7) 0.0198(2) Uani d . 1 . .
O O7 0.86143(14) 0.63490(10) 0.54849(7) 0.0249(2) Uani d . 1 . .
O O8 0.23749(13) 0.69600(10) 0.35796(7) 0.0210(2) Uani d . 1 . .
N N1 0.42880(18) 1.09155(12) 0.24520(9) 0.0240(3) Uani d . 1 . .
C C1 0.25053(18) 0.55935(13) 0.16689(10) 0.0163(3) Uani d . 1 . .
C C2 0.20715(19) 0.67463(13) 0.11028(10) 0.0180(3) Uani d . 1 . .
H H2A 0.0969 0.6553 0.0515 0.022 Uiso calc R 1 . .
C C3 0.31798(19) 0.80537(13) 0.13907(10) 0.0186(3) Uani d . 1 . .
H H3A 0.4224 0.8247 0.2010 0.022 Uiso calc R 1 . .
C C4 0.28680(19) 0.92101(13) 0.07998(10) 0.0185(3) Uani d . 1 . .
C C5 0.34552(19) 1.05839(14) 0.12818(10) 0.0191(3) Uani d . 1 . .
C C6 0.3278(2) 1.17065(14) 0.07231(11) 0.0210(3) Uani d . 1 . .
H H6A 0.3692 1.2607 0.1069 0.025 Uiso calc R 1 . .
C C7 0.24566(19) 1.13955(14) -0.03640(11) 0.0207(3) Uani d . 1 . .
C C8 0.1851(2) 1.00527(14) -0.08729(11) 0.0224(3) Uani d . 1 . .
C C9 0.2033(2) 0.89551(14) -0.03263(11) 0.0217(3) Uani d . 1 . .
H H9A 0.1616 0.8063 -0.0688 0.026 Uiso calc R 1 . .
C C10 0.41339(19) 0.58819(13) 0.26927(10) 0.0169(3) Uani d . 1 . .
C C11 0.40319(19) 0.65461(13) 0.36469(10) 0.0177(3) Uani d . 1 . .
C C12 0.55162(19) 0.67427(13) 0.46034(10) 0.0193(3) Uani d . 1 . .
H H12A 0.5443 0.7196 0.5234 0.023 Uiso calc R 1 . .
C C13 0.71059(19) 0.62434(13) 0.45897(11) 0.0195(3) Uani d . 1 . .
C C14 0.72776(19) 0.55933(13) 0.36521(11) 0.0194(3) Uani d . 1 . .
H H14A 0.8367 0.5281 0.3656 0.023 Uiso calc R 1 . .
C C15 0.57876(19) 0.54221(13) 0.27107(10) 0.0169(3) Uani d . 1 . .
C C16 0.1199(2) 1.14409(14) -0.21227(11) 0.0261(3) Uani d . 1 . .
H H16A 0.1968 1.1736 -0.2631 0.031 Uiso calc R 1 . .
H H16B -0.0115 1.1523 -0.2414 0.031 Uiso calc R 1 . .
C C17 0.7629(2) 0.46353(15) 0.16380(12) 0.0242(3) Uani d . 1 . .
H H17A 0.7548 0.4414 0.0890 0.036 Uiso calc R 1 . .
H H17B 0.7868 0.3887 0.2025 0.036 Uiso calc R 1 . .
H H17C 0.8687 0.5460 0.1934 0.036 Uiso calc R 1 . .
C C18 0.8713(2) 0.72180(16) 0.64213(12) 0.0313(4) Uani d . 1 . .
H H18A 0.9939 0.7326 0.6950 0.047 Uiso calc R 1 . .
H H18B 0.7640 0.6807 0.6718 0.047 Uiso calc R 1 . .
H H18C 0.8627 0.8105 0.6226 0.047 Uiso calc R 1 . .
C C19 0.2283(2) 0.77177(15) 0.45311(11) 0.0245(3) Uani d . 1 . .
H H19A 0.1095 0.7994 0.4380 0.037 Uiso calc R 1 . .
H H19B 0.3401 0.8522 0.4749 0.037 Uiso calc R 1 . .
H H19C 0.2289 0.7144 0.5102 0.037 Uiso calc R 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'
N N 0.0061 0.0033 '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
_geom_angle_publ_flag
C8 O4 C16 . . 106.10(10) ?
C7 O5 C16 . . 106.10(10) ?
C15 O6 C17 . . 117.41(10) ?
C13 O7 C18 . . 117.45(11) ?
C11 O8 C19 . . 116.76(10) ?
O2 N1 O3 . . 123.06(12) ?
O2 N1 C5 . . 117.74(11) ?
O3 N1 C5 . . 119.18(11) ?
O1 C1 C2 . . 119.91(12) ?
O1 C1 C10 . . 120.19(11) ?
C2 C1 C10 . . 119.86(11) ?
C3 C2 C1 . . 123.32(12) ?
C3 C2 H2A . . 118.3 ?
C1 C2 H2A . . 118.3 ?
C2 C3 C4 . . 124.64(12) ?
C2 C3 H3A . . 117.7 ?
C4 C3 H3A . . 117.7 ?
C5 C4 C9 . . 117.26(12) ?
C5 C4 C3 . . 123.70(12) ?
C9 C4 C3 . . 118.94(12) ?
C6 C5 C4 . . 124.53(12) ?
C6 C5 N1 . . 115.44(11) ?
C4 C5 N1 . . 120.02(12) ?
C7 C6 C5 . . 115.53(12) ?
C7 C6 H6A . . 122.2 ?
C5 C6 H6A . . 122.2 ?
C6 C7 O5 . . 127.98(12) ?
C6 C7 C8 . . 121.86(12) ?
O5 C7 C8 . . 110.16(12) ?
O4 C8 C9 . . 127.62(12) ?
O4 C8 C7 . . 109.79(12) ?
C9 C8 C7 . . 122.58(12) ?
C8 C9 C4 . . 118.24(12) ?
C8 C9 H9A . . 120.9 ?
C4 C9 H9A . . 120.9 ?
C11 C10 C15 . . 118.31(12) ?
C11 C10 C1 . . 122.38(11) ?
C15 C10 C1 . . 119.26(11) ?
O8 C11 C12 . . 122.95(12) ?
O8 C11 C10 . . 115.53(11) ?
C12 C11 C10 . . 121.51(12) ?
C13 C12 C11 . . 118.22(12) ?
C13 C12 H12A . . 120.9 ?
C11 C12 H12A . . 120.9 ?
O7 C13 C12 . . 123.09(12) ?
O7 C13 C14 . . 114.85(12) ?
C12 C13 C14 . . 122.06(12) ?
C15 C14 C13 . . 118.46(12) ?
C15 C14 H14A . . 120.8 ?
C13 C14 H14A . . 120.8 ?
O6 C15 C14 . . 124.12(12) ?
O6 C15 C10 . . 114.43(11) ?
C14 C15 C10 . . 121.42(12) ?
O5 C16 O4 . . 107.78(10) ?
O5 C16 H16A . . 110.1 ?
O4 C16 H16A . . 110.1 ?
O5 C16 H16B . . 110.1 ?
O4 C16 H16B . . 110.1 ?
H16A C16 H16B . . 108.5 ?
O6 C17 H17A . . 109.5 ?
O6 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
O6 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
O7 C18 H18A . . 109.5 ?
O7 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
O7 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
O8 C19 H19A . . 109.5 ?
O8 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
O8 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
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 C1 . 1.2234(16) ?
O2 N1 . 1.2257(16) ?
O3 N1 . 1.2257(16) ?
O4 C8 . 1.3651(16) ?
O4 C16 . 1.4372(17) ?
O5 C7 . 1.3644(16) ?
O5 C16 . 1.4310(17) ?
O6 C15 . 1.3615(15) ?
O6 C17 . 1.4299(16) ?
O7 C13 . 1.3649(16) ?
O7 C18 . 1.4280(17) ?
O8 C11 . 1.3677(15) ?
O8 C19 . 1.4339(16) ?
N1 C5 . 1.4637(17) ?
C1 C2 . 1.4732(18) ?
C1 C10 . 1.5007(18) ?
C2 C3 . 1.3337(19) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.4680(18) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.4017(19) ?
C4 C9 . 1.4092(18) ?
C5 C6 . 1.3954(19) ?
C6 C7 . 1.3642(19) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.3847(19) ?
C8 C9 . 1.3657(19) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.3946(18) ?
C10 C15 . 1.4009(18) ?
C11 C12 . 1.3941(19) ?
C12 C13 . 1.3874(19) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.3905(19) ?
C14 C15 . 1.3862(19) ?
C14 H14A . 0.9300 ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
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
C2 H2A O1 2_565 0.93 2.55 3.4512(16) 164.4
C6 H6A O6 1_565 0.93 2.36 3.2429(16) 158.0
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C3 . . . . -171.07(12) ?
C10 C1 C2 C3 . . . . 6.82(19) ?
C1 C2 C3 C4 . . . . 175.54(12) ?
C2 C3 C4 C5 . . . . 153.75(13) ?
C2 C3 C4 C9 . . . . -29.9(2) ?
C9 C4 C5 C6 . . . . -0.4(2) ?
C3 C4 C5 C6 . . . . 176.01(12) ?
C9 C4 C5 N1 . . . . 178.47(12) ?
C3 C4 C5 N1 . . . . -5.2(2) ?
O2 N1 C5 C6 . . . . -31.32(18) ?
O3 N1 C5 C6 . . . . 146.93(13) ?
O2 N1 C5 C4 . . . . 149.75(14) ?
O3 N1 C5 C4 . . . . -32.00(19) ?
C4 C5 C6 C7 . . . . 0.4(2) ?
N1 C5 C6 C7 . . . . -178.43(11) ?
C5 C6 C7 O5 . . . . 179.77(13) ?
C5 C6 C7 C8 . . . . -0.2(2) ?
C16 O5 C7 C6 . . . . -179.08(14) ?
C16 O5 C7 C8 . . . . 0.93(15) ?
C16 O4 C8 C9 . . . . 178.84(14) ?
C16 O4 C8 C7 . . . . -1.85(16) ?
C6 C7 C8 O4 . . . . -179.39(13) ?
O5 C7 C8 O4 . . . . 0.60(17) ?
C6 C7 C8 C9 . . . . 0.0(2) ?
O5 C7 C8 C9 . . . . 179.95(13) ?
O4 C8 C9 C4 . . . . 179.36(13) ?
C7 C8 C9 C4 . . . . 0.1(2) ?
C5 C4 C9 C8 . . . . 0.05(19) ?
C3 C4 C9 C8 . . . . -176.50(12) ?
O1 C1 C10 C11 . . . . -114.47(14) ?
C2 C1 C10 C11 . . . . 67.64(16) ?
O1 C1 C10 C15 . . . . 62.88(17) ?
C2 C1 C10 C15 . . . . -115.00(13) ?
C19 O8 C11 C12 . . . . 4.76(18) ?
C19 O8 C11 C10 . . . . -176.43(11) ?
C15 C10 C11 O8 . . . . -179.48(11) ?
C1 C10 C11 O8 . . . . -2.09(18) ?
C15 C10 C11 C12 . . . . -0.65(19) ?
C1 C10 C11 C12 . . . . 176.73(12) ?
O8 C11 C12 C13 . . . . 177.98(11) ?
C10 C11 C12 C13 . . . . -0.76(19) ?
C18 O7 C13 C12 . . . . -11.05(19) ?
C18 O7 C13 C14 . . . . 168.92(12) ?
C11 C12 C13 O7 . . . . -178.33(12) ?
C11 C12 C13 C14 . . . . 1.7(2) ?
O7 C13 C14 C15 . . . . 178.85(11) ?
C12 C13 C14 C15 . . . . -1.19(19) ?
C17 O6 C15 C14 . . . . -11.24(17) ?
C17 O6 C15 C10 . . . . 166.67(11) ?
C13 C14 C15 O6 . . . . 177.46(11) ?
C13 C14 C15 C10 . . . . -0.30(19) ?
C11 C10 C15 O6 . . . . -176.77(10) ?
C1 C10 C15 O6 . . . . 5.76(17) ?
C11 C10 C15 C14 . . . . 1.19(19) ?
C1 C10 C15 C14 . . . . -176.27(11) ?
C7 O5 C16 O4 . . . . -2.04(15) ?
C8 O4 C16 O5 . . . . 2.40(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743292
