#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/32/2223253.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_2223253
loop_
_publ_author_name
'Zhou, Meng'
'Li, Rui'
'Ding, Zhen-Yu'
_publ_section_title
;
 2,2-Dimethyl-5-[(3-nitroanilino)methylene]-1,3-dioxane-4,6-dione
;
_journal_coeditor_code           ZQ2002
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2171
_journal_paper_doi               10.1107/S1600536809031535
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H12 N2 O6'
_chemical_formula_moiety         'C13 H12 N2 O6'
_chemical_formula_sum            'C13 H12 N2 O6'
_chemical_formula_weight         292.25
_chemical_name_systematic
;
2,2-Dimethyl-5-[(3-nitroanilino)methylene]-1,3-dioxane-4,6-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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.8640(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7900(13)
_cell_length_b                   8.7699(9)
_cell_length_c                   14.0614(15)
_cell_measurement_reflns_used    4305
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      2.3
_cell_volume                     1329.6(2)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0135
_diffrn_reflns_av_sigmaI/netI    0.0157
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8116
_diffrn_reflns_theta_full        27.6
_diffrn_reflns_theta_max         27.6
_diffrn_reflns_theta_min         2.8
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.18
_refine_ls_extinction_coef       0.0195(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         3052
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.043
_refine_ls_R_factor_gt           0.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.045P)²+0.3157P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.095
_refine_ls_wR_factor_ref         0.101
_reflns_number_gt                2572
_reflns_number_total             3052
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zq2002.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               2223253
_cod_database_fobs_code          2223253
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
O O1 0.45433(8) -0.09916(10) 1.23372(6) 0.0370(2) Uani d . 1 . .
O O3 0.47419(8) -0.05487(12) 1.08661(7) 0.0440(2) Uani d . 1 . .
O O2 0.25826(8) -0.13984(11) 1.23681(6) 0.0401(2) Uani d . 1 . .
C C4 0.40464(11) -0.06725(13) 1.13054(9) 0.0322(2) Uani d . 1 . .
N N1 0.26298(10) 0.01843(13) 0.91248(8) 0.0359(2) Uani d . 1 . .
C C8 0.19585(11) 0.06369(14) 0.80763(9) 0.0342(3) Uani d . 1 . .
C C9 0.24224(11) 0.02544(14) 0.73506(9) 0.0347(3) Uani d . 1 . .
H H9 0.3148 -0.0312 0.7538 0.042 Uiso calc R 1 . .
C C3 0.37852(11) -0.07324(14) 1.29110(9) 0.0337(3) Uani d . 1 . .
O O4 0.08565(9) -0.12773(15) 1.09442(8) 0.0584(3) Uani d . 1 . .
C C7 0.21114(11) -0.01291(14) 0.97781(9) 0.0350(3) Uani d . 1 . .
H H7 0.1252 -0.0055 0.9519 0.042 Uiso calc R 1 . .
O O5 0.30012(13) -0.07262(15) 0.57581(10) 0.0684(3) Uani d . 1 . .
C C6 0.19637(11) -0.10611(15) 1.13438(9) 0.0381(3) Uani d . 1 . .
C C5 0.27159(11) -0.05534(14) 1.08029(9) 0.0333(3) Uani d . 1 . .
C C10 0.17796(12) 0.07365(16) 0.63388(9) 0.0403(3) Uani d . 1 . .
C C13 0.08587(14) 0.14495(19) 0.77793(11) 0.0510(4) Uani d . 1 . .
H H13 0.0545 0.1705 0.8268 0.061 Uiso calc R 1 . .
C C2 0.43836(14) -0.16096(17) 1.39116(10) 0.0459(3) Uani d . 1 . .
H H2A 0.3876 -0.1539 1.4299 0.069 Uiso calc R 1 . .
H H2B 0.5188 -0.1189 1.4315 0.069 Uiso calc R 1 . .
H H2C 0.4468 -0.2660 1.3759 0.069 Uiso calc R 1 . .
N N2 0.22862(12) 0.03454(17) 0.55739(9) 0.0535(3) Uani d . 1 . .
C C1 0.36712(15) 0.09463(15) 1.30692(11) 0.0481(3) Uani d . 1 . .
H H1A 0.3285 0.1440 1.2406 0.072 Uiso calc R 1 . .
H H1B 0.4481 0.1372 1.3444 0.072 Uiso calc R 1 . .
H H1C 0.3174 0.1099 1.3459 0.072 Uiso calc R 1 . .
C C11 0.06978(15) 0.1552(2) 0.60191(11) 0.0586(4) Uani d . 1 . .
H H11 0.0293 0.1874 0.5334 0.070 Uiso calc R 1 . .
O O6 0.19778(16) 0.1124(2) 0.47934(10) 0.0992(6) Uani d . 1 . .
C C12 0.02320(15) 0.1877(2) 0.67512(13) 0.0672(5) Uani d . 1 . .
H H12 -0.0518 0.2393 0.6550 0.081 Uiso calc R 1 . .
H H1 0.3441(15) 0.0100(18) 0.9339(12) 0.051(4) Uiso 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
C4 O1 C3 . . 117.92(9) ?
C6 O2 C3 . . 117.84(9) ?
O3 C4 O1 . . 118.31(11) ?
O3 C4 C5 . . 124.71(11) ?
O1 C4 C5 . . 116.96(10) ?
C7 N1 C8 . . 124.04(10) ?
C7 N1 H1 . . 119.2(10) ?
C8 N1 H1 . . 116.7(10) ?
C9 C8 C13 . . 120.26(11) ?
C9 C8 N1 . . 118.62(11) ?
C13 C8 N1 . . 121.12(11) ?
C8 C9 C10 . . 118.11(11) ?
C8 C9 H9 . . 120.9 ?
C10 C9 H9 . . 120.9 ?
O2 C3 O1 . . 109.91(9) ?
O2 C3 C1 . . 110.44(11) ?
O1 C3 C1 . . 110.45(10) ?
O2 C3 C2 . . 106.13(10) ?
O1 C3 C2 . . 106.25(10) ?
C1 C3 C2 . . 113.48(11) ?
N1 C7 C5 . . 126.51(11) ?
N1 C7 H7 . . 116.7 ?
C5 C7 H7 . . 116.7 ?
O4 C6 O2 . . 118.33(11) ?
O4 C6 C5 . . 125.30(12) ?
O2 C6 C5 . . 116.25(10) ?
C7 C5 C4 . . 122.25(10) ?
C7 C5 C6 . . 117.66(11) ?
C4 C5 C6 . . 119.70(10) ?
C11 C10 C9 . . 123.24(12) ?
C11 C10 N2 . . 118.87(12) ?
C9 C10 N2 . . 117.88(12) ?
C12 C13 C8 . . 119.52(13) ?
C12 C13 H13 . . 120.2 ?
C8 C13 H13 . . 120.2 ?
C3 C2 H2A . . 109.5 ?
C3 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
C3 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
O6 N2 O5 . . 123.59(14) ?
O6 N2 C10 . . 117.94(14) ?
O5 N2 C10 . . 118.46(12) ?
C3 C1 H1A . . 109.5 ?
C3 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C3 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C10 C11 C12 . . 117.54(13) ?
C10 C11 H11 . . 121.2 ?
C12 C11 H11 . . 121.2 ?
C11 C12 C13 . . 121.26(14) ?
C11 C12 H12 . . 119.4 ?
C13 C12 H12 . . 119.4 ?
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 C4 . 1.3560(14) ?
O1 C3 . 1.4441(14) ?
O3 C4 . 1.2147(14) ?
O2 C6 . 1.3580(15) ?
O2 C3 . 1.4348(15) ?
C4 C5 . 1.4401(17) ?
N1 C7 . 1.3219(15) ?
N1 C8 . 1.4190(15) ?
N1 H1 . 0.882(16) ?
C8 C9 . 1.3800(17) ?
C8 C13 . 1.3875(18) ?
C9 C10 . 1.3802(17) ?
C9 H9 . 0.9300 ?
C3 C1 . 1.5030(18) ?
C3 C2 . 1.5053(17) ?
O4 C6 . 1.2092(16) ?
C7 C5 . 1.3754(16) ?
C7 H7 . 0.9300 ?
O5 N2 . 1.2183(18) ?
C6 C5 . 1.4524(16) ?
C10 C11 . 1.370(2) ?
C10 N2 . 1.4665(17) ?
C13 C12 . 1.383(2) ?
C13 H13 . 0.9300 ?
C2 H2A . 0.9600 ?
C2 H2B . 0.9600 ?
C2 H2C . 0.9600 ?
N2 O6 . 1.2164(17) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C11 C12 . 1.378(2) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
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
N1 H1 O3 . 0.882(16) 2.150(15) 2.7705(14) 126.8(13)
N1 H1 O3 3_657 0.882(16) 2.308(16) 3.1101(14) 151.2(13)
C7 H7 O4 . 0.93 2.48 2.8026(18) 101
C7 H7 O4 3_557 0.93 2.58 3.4527(18) 156
C11 H11 O4 2_556 0.93 2.39 3.242(2) 152
C13 H13 O4 3_557 0.93 2.36 3.205(2) 151
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
C3 O1 C4 O3 . . . . 163.48(11) ?
C3 O1 C4 C5 . . . . -18.46(15) ?
C7 N1 C8 C9 . . . . -149.73(12) ?
C7 N1 C8 C13 . . . . 30.4(2) ?
C13 C8 C9 C10 . . . . 1.64(19) ?
N1 C8 C9 C10 . . . . -178.26(11) ?
C6 O2 C3 O1 . . . . -50.49(14) ?
C6 O2 C3 C1 . . . . 71.61(13) ?
C6 O2 C3 C2 . . . . -164.99(10) ?
C4 O1 C3 O2 . . . . 48.46(13) ?
C4 O1 C3 C1 . . . . -73.64(14) ?
C4 O1 C3 C2 . . . . 162.88(10) ?
C8 N1 C7 C5 . . . . -179.14(12) ?
C3 O2 C6 O4 . . . . -161.51(12) ?
C3 O2 C6 C5 . . . . 22.23(16) ?
N1 C7 C5 C4 . . . . 1.6(2) ?
N1 C7 C5 C6 . . . . -171.23(12) ?
O3 C4 C5 C7 . . . . -6.8(2) ?
O1 C4 C5 C7 . . . . 175.30(11) ?
O3 C4 C5 C6 . . . . 165.88(12) ?
O1 C4 C5 C6 . . . . -12.04(17) ?
O4 C6 C5 C7 . . . . 7.2(2) ?
O2 C6 C5 C7 . . . . -176.78(11) ?
O4 C6 C5 C4 . . . . -165.75(14) ?
O2 C6 C5 C4 . . . . 10.23(18) ?
C8 C9 C10 C11 . . . . -1.1(2) ?
C8 C9 C10 N2 . . . . 179.15(11) ?
C9 C8 C13 C12 . . . . -0.1(2) ?
N1 C8 C13 C12 . . . . 179.74(15) ?
C11 C10 N2 O6 . . . . 22.6(2) ?
C9 C10 N2 O6 . . . . -157.58(15) ?
C11 C10 N2 O5 . . . . -158.17(16) ?
C9 C10 N2 O5 . . . . 21.6(2) ?
C9 C10 C11 C12 . . . . -1.0(3) ?
N2 C10 C11 C12 . . . . 178.78(16) ?
C10 C11 C12 C13 . . . . 2.5(3) ?
C8 C13 C12 C11 . . . . -2.0(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9002764
