#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/89/2228941.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_2228941
loop_
_publ_author_name
'Shi, Jian-you'
'Li, Jin-qi'
'Tong, Rong-sheng'
'Lin, He'
'Lu, Chen'
_publ_section_title
;
 2,2-Dimethyl-5-[(pyridin-2-ylamino)methylidene]-1,3-dioxane-4,6-dione
;
_journal_coeditor_code           BH2327
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o253
_journal_paper_doi               10.1107/S1600536810053250
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C12 H12 N2 O4'
_chemical_formula_moiety         'C12 H12 N2 O4'
_chemical_formula_sum            'C12 H12 N2 O4'
_chemical_formula_weight         248.24
_chemical_name_systematic
;
2,2-Dimethyl-5-[(pyridin-2-ylamino)methylidene]-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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.601(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7344(10)
_cell_length_b                   13.9712(15)
_cell_length_c                   9.4744(11)
_cell_measurement_reflns_used    1780
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1459
_cell_measurement_theta_min      3.0463
_cell_volume                     1152.4(2)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
'Oxford Diffraction Xcalibur diffractometer with an Eos CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4873
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.38
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.99713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.140
_refine_ls_extinction_coef       0.0060(9)
_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   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2334
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0396
_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)+(0.0383P)²+0.0655P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0959
_reflns_number_gt                1659
_reflns_number_total             2334
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2327.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228941
_cod_database_fobs_code          2228941
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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 O3 0.21039(13) 0.15916(7) 0.50800(11) 0.0497(3) Uani d . 1 . .
O O4 0.37760(12) 0.11610(7) 0.33485(12) 0.0504(3) Uani d . 1 . .
C C6 0.22965(17) -0.10004(11) 0.49185(16) 0.0421(4) Uani d U 1 . .
H H6 0.1613 -0.1134 0.5596 0.050 Uiso calc R 1 . .
O O1 0.10857(14) 0.05240(7) 0.64457(11) 0.0556(3) Uani d . 1 . .
O O2 0.44968(12) -0.03377(8) 0.30745(12) 0.0559(3) Uani d . 1 . .
N N2 0.29233(14) -0.17386(8) 0.43038(13) 0.0455(3) Uani d . 1 . .
H H2 0.3571 -0.1614 0.3692 0.055 Uiso calc R 1 . .
C C7 0.25719(16) -0.00541(10) 0.46383(15) 0.0388(3) Uani d U 1 . .
N N1 0.17056(15) -0.28950(8) 0.55799(13) 0.0474(4) Uani d . 1 . .
C C1 0.1423(2) -0.38227(11) 0.58158(18) 0.0532(4) Uani d . 1 . .
H H1 0.0776 -0.3976 0.6515 0.064 Uiso calc R 1 . .
C C9 0.18429(18) 0.06634(10) 0.54492(16) 0.0428(4) Uani d . 1 . .
C C8 0.36562(17) 0.02142(11) 0.36380(16) 0.0434(4) Uani d . 1 . .
C C5 0.26224(16) -0.27096(10) 0.45637(16) 0.0400(4) Uani d . 1 . .
C C3 0.2993(2) -0.43431(11) 0.40519(18) 0.0547(5) Uani d . 1 . .
H H3 0.3432 -0.4829 0.3548 0.066 Uiso calc R 1 . .
C C4 0.32929(19) -0.34013(11) 0.37743(17) 0.0487(4) Uani d . 1 . .
H H4 0.3930 -0.3233 0.3074 0.058 Uiso calc R 1 . .
C C12 0.11654(19) 0.16341(11) 0.26210(16) 0.0493(4) Uani d . 1 . .
H H12B 0.1452 0.1783 0.1689 0.074 Uiso calc R 1 . .
H H12C 0.0343 0.2048 0.2851 0.074 Uiso calc R 1 . .
H H12A 0.0833 0.0980 0.2649 0.074 Uiso calc R 1 . .
C C11 0.3145(2) 0.27839(11) 0.36841(19) 0.0606(5) Uani d . 1 . .
H H11A 0.3519 0.2923 0.2781 0.091 Uiso calc R 1 . .
H H11C 0.3969 0.2843 0.4412 0.091 Uiso calc R 1 . .
H H11B 0.2342 0.3226 0.3864 0.091 Uiso calc R 1 . .
C C2 0.2036(2) -0.45560(11) 0.50844(18) 0.0582(5) Uani d . 1 . .
H H2A 0.1806 -0.5189 0.5286 0.070 Uiso calc R 1 . .
C C10 0.25227(18) 0.17780(10) 0.36764(16) 0.0439(4) 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
O3 C9 C7 . . 115.68(13) ?
O3 C10 O4 . . 110.21(11) ?
O3 C10 C12 . . 110.33(13) ?
O3 C10 C11 . . 106.51(12) ?
O4 C8 C7 . . 116.85(13) ?
O4 C10 C12 . . 110.35(12) ?
O4 C10 C11 . . 106.15(13) ?
C6 N2 H2 . . 117.1 ?
C6 N2 C5 . . 125.74(13) ?
C6 C7 C9 . . 118.33(13) ?
C6 C7 C8 . . 120.77(14) ?
O1 C9 O3 . . 117.68(13) ?
O1 C9 C7 . . 126.57(14) ?
O2 C8 O4 . . 118.03(13) ?
O2 C8 C7 . . 125.08(14) ?
N2 C6 H6 . . 117.3 ?
N2 C6 C7 . . 125.42(14) ?
C7 C6 H6 . . 117.3 ?
N1 C1 H1 . . 118.2 ?
N1 C1 C2 . . 123.64(15) ?
N1 C5 N2 . . 116.58(13) ?
N1 C5 C4 . . 124.30(14) ?
C1 C2 H2A . . 120.5 ?
C9 O3 C10 . . 118.08(11) ?
C9 C7 C8 . . 120.72(13) ?
C8 O4 C10 . . 117.75(11) ?
C5 N2 H2 . . 117.1 ?
C5 N1 C1 . . 116.06(13) ?
C5 C4 H4 . . 120.9 ?
C3 C4 C5 . . 118.16(15) ?
C3 C4 H4 . . 120.9 ?
C3 C2 C1 . . 118.99(15) ?
C3 C2 H2A . . 120.5 ?
C4 C5 N2 . . 119.12(13) ?
C4 C3 H3 . . 120.6 ?
C12 C10 C11 . . 113.15(13) ?
H12B C12 H12C . . 109.5 ?
H12B C12 H12A . . 109.5 ?
H12C C12 H12A . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11A C11 H11B . . 109.5 ?
H11C C11 H11B . . 109.5 ?
C2 C1 H1 . . 118.2 ?
C2 C3 H3 . . 120.6 ?
C2 C3 C4 . . 118.84(15) ?
C10 C12 H12B . . 109.5 ?
C10 C12 H12C . . 109.5 ?
C10 C12 H12A . . 109.5 ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11C . . 109.5 ?
C10 C11 H11B . . 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
O3 C9 . 1.3671(16) ?
O3 C10 . 1.4311(18) ?
O4 C8 . 1.3567(17) ?
O4 C10 . 1.4465(18) ?
C6 H6 . 0.9300 ?
C6 N2 . 1.3242(18) ?
C6 C7 . 1.374(2) ?
O1 C9 . 1.2112(17) ?
O2 C8 . 1.2172(17) ?
N2 H2 . 0.8600 ?
N2 C5 . 1.4072(18) ?
C7 C9 . 1.442(2) ?
C7 C8 . 1.442(2) ?
N1 C1 . 1.3415(19) ?
N1 C5 . 1.3263(18) ?
C1 H1 . 0.9300 ?
C1 C2 . 1.370(2) ?
C5 C4 . 1.381(2) ?
C3 H3 . 0.9300 ?
C3 C4 . 1.371(2) ?
C3 C2 . 1.370(2) ?
C4 H4 . 0.9300 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C12 H12A . 0.9600 ?
C12 C10 . 1.502(2) ?
C11 H11A . 0.9600 ?
C11 H11C . 0.9600 ?
C11 H11B . 0.9600 ?
C11 C10 . 1.507(2) ?
C2 H2A . 0.9300 ?
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
C6 N2 C5 N1 . . . . -4.6(2) ?
C6 N2 C5 C4 . . . . 175.96(15) ?
C6 C7 C9 O3 . . . . -177.16(12) ?
C6 C7 C9 O1 . . . . 6.0(2) ?
C6 C7 C8 O4 . . . . 175.36(13) ?
C6 C7 C8 O2 . . . . -7.0(2) ?
N2 C6 C7 C9 . . . . -177.35(14) ?
N2 C6 C7 C8 . . . . -2.2(2) ?
N2 C5 C4 C3 . . . . 179.53(14) ?
C7 C6 N2 C5 . . . . -178.57(14) ?
N1 C1 C2 C3 . . . . 0.0(3) ?
N1 C5 C4 C3 . . . . 0.2(2) ?
C1 N1 C5 N2 . . . . 179.83(13) ?
C1 N1 C5 C4 . . . . -0.8(2) ?
C9 O3 C10 O4 . . . . -50.35(17) ?
C9 O3 C10 C12 . . . . 71.76(16) ?
C9 O3 C10 C11 . . . . -165.07(13) ?
C9 C7 C8 O4 . . . . -9.6(2) ?
C9 C7 C8 O2 . . . . 168.03(15) ?
C8 O4 C10 O3 . . . . 47.99(17) ?
C8 O4 C10 C12 . . . . -74.10(16) ?
C8 O4 C10 C11 . . . . 162.95(12) ?
C8 C7 C9 O3 . . . . 7.7(2) ?
C8 C7 C9 O1 . . . . -169.19(15) ?
C5 N1 C1 C2 . . . . 0.7(2) ?
C4 C3 C2 C1 . . . . -0.7(3) ?
C2 C3 C4 C5 . . . . 0.6(2) ?
C10 O3 C9 O1 . . . . -159.37(14) ?
C10 O3 C9 C7 . . . . 23.48(19) ?
C10 O4 C8 O2 . . . . 162.84(14) ?
C10 O4 C8 C7 . . . . -19.38(19) ?
