#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/05/2220561.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_2220561
loop_
_publ_author_name
'Wu, Chuanbing'
_publ_section_title
;
 3-(3-Nitrobenzylidene)pentane-2,4-dione
;
_journal_coeditor_code           IS2374
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o210
_journal_paper_doi               10.1107/S1600536808043456
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C12 H11 N O4'
_chemical_formula_moiety         'C12 H11 N O4'
_chemical_formula_sum            'C12 H11 N O4'
_chemical_formula_weight         233.22
_chemical_name_systematic
;
3-(3-Nitrobenzylidene)pentane-2,4-dione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 114.1170(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.0634(9)
_cell_length_b                   5.2470(3)
_cell_length_c                   14.9774(9)
_cell_measurement_reflns_used    1131
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.32
_cell_measurement_theta_min      2.73
_cell_volume                     1152.18(12)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker SMART 4K CCD area-detector'
_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  0.0477
_diffrn_reflns_av_sigmaI/netI    0.0606
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4779
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.73
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.165
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         1998
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.1008
_refine_ls_R_factor_gt           0.0681
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.085P)²+0.2322P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1598
_refine_ls_wR_factor_ref         0.1707
_reflns_number_gt                1400
_reflns_number_total             1998
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2374.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2220561
_cod_database_fobs_code          2220561
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
C C1 0.37414(19) -0.0732(5) 0.46603(19) 0.0328(7) Uani d . 1 . .
C C2 0.31796(19) 0.1238(5) 0.4642(2) 0.0359(7) Uani d . 1 . .
C C3 0.30722(19) 0.1886(5) 0.54900(19) 0.0348(7) Uani d . 1 . .
C C4 0.3576(2) 0.0531(6) 0.6342(2) 0.0405(8) Uani d . 1 . .
C C5 0.4149(2) -0.1425(6) 0.6345(2) 0.0458(8) Uani d . 1 . .
C C6 0.4239(2) -0.2098(6) 0.5501(2) 0.0399(8) Uani d . 1 . .
C C7 0.2427(2) 0.3821(5) 0.5535(2) 0.0389(8) Uani d . 1 . .
C C8 0.1758(2) 0.5058(5) 0.4812(2) 0.0361(7) Uani d . 1 . .
C C9 0.1551(2) 0.4824(5) 0.3737(2) 0.0374(7) Uani d . 1 . .
C C10 0.0895(2) 0.2825(6) 0.3165(2) 0.0536(9) Uani d . 1 . .
C C11 0.1120(2) 0.6808(6) 0.5006(2) 0.0434(8) Uani d . 1 . .
C C12 0.1252(3) 0.7457(7) 0.6020(2) 0.0606(10) Uani d . 1 . .
H H2 0.2871 0.2142 0.4066 0.043 Uiso calc R 1 . .
H H4 0.3524 0.0957 0.6919 0.049 Uiso calc R 1 . .
H H5 0.4478 -0.2299 0.6923 0.055 Uiso calc R 1 . .
H H6 0.4621 -0.3426 0.5496 0.048 Uiso calc R 1 . .
H H7 0.2494 0.4254 0.6163 0.047 Uiso calc R 1 . .
H H10A 0.0808 0.2920 0.2492 0.080 Uiso calc R 1 . .
H H10B 0.0322 0.3087 0.3211 0.080 Uiso calc R 1 . .
H H10C 0.1132 0.1177 0.3423 0.080 Uiso calc R 1 . .
H H12A 0.0831 0.8774 0.6004 0.091 Uiso calc R 1 . .
H H12B 0.1865 0.8045 0.6380 0.091 Uiso calc R 1 . .
H H12C 0.1146 0.5971 0.6333 0.091 Uiso calc R 1 . .
O O1 0.34549(17) -0.0057(5) 0.30328(15) 0.0605(7) Uani d . 1 . .
O O2 0.4208(2) -0.3406(5) 0.37212(17) 0.0735(9) Uani d . 1 . .
O O3 0.19108(17) 0.6251(4) 0.33704(16) 0.0612(7) Uani d . 1 . .
O O4 0.04744(19) 0.7640(5) 0.43075(17) 0.0764(9) Uani d . 1 . .
N N1 0.38064(17) -0.1449(5) 0.37404(18) 0.0446(7) Uani d . 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
C1 C6 H6 . . 121.2 ?
C1 C2 C3 . . 119.6(3) ?
C1 C2 H2 . . 120.2 ?
C2 C3 C4 . . 117.9(3) ?
C2 C3 C7 . . 124.2(2) ?
C2 C1 C6 . . 122.8(3) ?
C2 C1 N1 . . 118.3(2) ?
C3 C2 H2 . . 120.2 ?
C3 C7 H7 . . 114.9 ?
C3 C4 H4 . . 119.3 ?
C4 C3 C7 . . 117.8(3) ?
C4 C5 H5 . . 119.7 ?
C5 C6 C1 . . 117.7(3) ?
C5 C6 H6 . . 121.1 ?
C5 C4 C3 . . 121.4(3) ?
C5 C4 H4 . . 119.3 ?
C6 C1 N1 . . 118.9(3) ?
C6 C5 C4 . . 120.6(3) ?
C6 C5 H5 . . 119.7 ?
C7 C8 C11 . . 121.9(3) ?
C7 C8 C9 . . 125.2(3) ?
C8 C7 C3 . . 130.1(3) ?
C8 C7 H7 . . 114.9 ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
C10 C9 C8 . . 117.8(3) ?
C11 C8 C9 . . 112.9(2) ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
C12 C11 C8 . . 121.2(3) ?
H10A C10 H10B . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
H12A C12 H12B . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
O1 N1 O2 . . 123.1(3) ?
O1 N1 C1 . . 118.4(2) ?
O2 N1 C1 . . 118.5(3) ?
O3 C9 C10 . . 122.4(3) ?
O3 C9 C8 . . 119.8(3) ?
O4 C11 C12 . . 120.9(3) ?
O4 C11 C8 . . 117.8(3) ?
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
C1 C6 . 1.384(4) ?
C2 C1 . 1.365(4) ?
C2 H2 . 0.9300 ?
C3 C2 . 1.392(4) ?
C3 C4 . 1.394(4) ?
C3 C7 . 1.472(4) ?
C4 C5 . 1.377(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.376(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C7 . 1.341(4) ?
C8 C11 . 1.490(4) ?
C8 C9 . 1.511(4) ?
C9 C10 . 1.485(4) ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 C12 . 1.486(4) ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
O3 C9 . 1.206(4) ?
O4 C11 . 1.214(3) ?
N1 O1 . 1.219(3) ?
N1 O2 . 1.219(3) ?
N1 C1 . 1.472(4) ?
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
C6 H6 O2 3_646 0.93 2.42 3.282(4) 153
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
C2 C1 C6 C5 . . . . 0.5(5) ?
C2 C3 C4 C5 . . . . -1.3(5) ?
C2 C3 C7 C8 . . . . 9.8(5) ?
C3 C2 C1 C6 . . . . -1.9(5) ?
C3 C2 C1 N1 . . . . 177.1(2) ?
C3 C4 C5 C6 . . . . -0.1(5) ?
C4 C5 C6 C1 . . . . 0.5(5) ?
C4 C3 C2 C1 . . . . 2.3(4) ?
C4 C3 C7 C8 . . . . -167.0(3) ?
C7 C3 C4 C5 . . . . 175.7(3) ?
C7 C8 C9 O3 . . . . -90.5(4) ?
C7 C3 C2 C1 . . . . -174.5(3) ?
C7 C8 C9 C10 . . . . 90.1(4) ?
C7 C8 C11 O4 . . . . -172.3(3) ?
C7 C8 C11 C12 . . . . 6.0(5) ?
C9 C8 C11 O4 . . . . 6.7(4) ?
C9 C8 C11 C12 . . . . -175.1(3) ?
C9 C8 C7 C3 . . . . -4.2(5) ?
C11 C8 C7 C3 . . . . 174.6(3) ?
C11 C8 C9 O3 . . . . 90.6(4) ?
C11 C8 C9 C10 . . . . -88.8(3) ?
O1 N1 C1 C2 . . . . 9.6(4) ?
O1 N1 C1 C6 . . . . -171.4(3) ?
O2 N1 C1 C6 . . . . 8.7(4) ?
O2 N1 C1 C2 . . . . -170.3(3) ?
N1 C1 C6 C5 . . . . -178.5(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 86658
