#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201978 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/63/2226380.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_2226380
loop_
_publ_author_name
'Çolak, Naki'
'Yıldırır, Yılmaz'
'Tercan, Barış'
'Ermiş, Emel'
'Hökelek, Tuncer'
_publ_section_title
;
 4-[2-(2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)hydrazin-1-yl]benzonitrile
;
_journal_coeditor_code           CI5104
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1784
_journal_page_last               o1785
_journal_paper_doi               10.1107/S1600536810024025
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H11 N3 O4'
_chemical_formula_moiety         'C13 H11 N3 O4'
_chemical_formula_sum            'C13 H11 N3 O4'
_chemical_formula_weight         273.25
_chemical_name_systematic
;
4-[2-(2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)hydrazin-1-yl]benzonitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 93.7960(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7617(2)
_cell_length_b                   11.0023(2)
_cell_length_c                   11.4753(3)
_cell_measurement_reflns_used    4103
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.37
_cell_measurement_theta_min      2.57
_cell_volume                     1229.76(5)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'Bruker Kappa 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  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11746
_diffrn_reflns_theta_full        28.45
_diffrn_reflns_theta_max         28.45
_diffrn_reflns_theta_min         2.57
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.9682
_exptl_absorpt_correction_T_min  0.9502
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.242
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3098
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0382
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0626P)²+0.2729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1076
_reflns_number_gt                2591
_reflns_number_total             3098
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci5104.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2226380
_cod_database_fobs_code          2226380
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.16363(8) 0.74524(7) 0.85585(7) 0.0172(2) Uani d . 1 . .
O O2 0.17892(8) 0.56739(7) 0.97179(7) 0.01470(19) Uani d . 1 . .
O O3 0.35656(9) 0.44276(8) 0.96914(7) 0.0187(2) Uani d . 1 . .
O O4 0.32521(9) 0.79574(8) 0.73794(8) 0.0249(2) Uani d . 1 . .
N N1 0.44403(10) 0.56888(9) 0.76510(9) 0.0165(2) Uani d . 1 . .
N N2 0.51381(10) 0.46953(9) 0.78943(9) 0.0159(2) Uani d . 1 . .
H H2 0.4942(16) 0.4243(15) 0.8538(15) 0.028(4) Uiso d . 1 . .
N N3 1.03756(11) 0.29578(10) 0.47015(10) 0.0232(2) Uani d . 1 . .
C C1 0.08704(11) 0.64589(10) 0.90176(10) 0.0143(2) Uani d . 1 . .
C C2 0.27845(12) 0.71950(11) 0.79881(10) 0.0172(2) Uani d . 1 . .
C C3 0.34022(12) 0.59901(10) 0.82608(10) 0.0155(2) Uani d . 1 . .
C C4 0.29477(11) 0.52812(10) 0.92521(10) 0.0144(2) Uani d . 1 . .
C C5 0.62374(11) 0.43844(10) 0.72180(10) 0.0148(2) Uani d . 1 . .
C C6 0.64458(13) 0.49922(11) 0.61746(10) 0.0173(2) Uani d . 1 . .
H H6 0.5852(15) 0.5636(14) 0.5904(13) 0.020(4) Uiso d . 1 . .
C C7 0.75216(13) 0.46401(11) 0.55177(10) 0.0175(2) Uani d . 1 . .
H H7 0.7668(15) 0.5059(14) 0.4788(13) 0.024(4) Uiso d . 1 . .
C C8 0.83788(12) 0.36875(11) 0.59035(10) 0.0155(2) Uani d . 1 . .
C C9 0.81720(12) 0.30898(11) 0.69557(10) 0.0161(2) Uani d . 1 . .
H H9 0.8752(14) 0.2457(14) 0.7224(12) 0.020(4) Uiso d . 1 . .
C C10 0.70992(12) 0.34407(11) 0.76131(10) 0.0159(2) Uani d . 1 . .
H H10 0.6926(14) 0.3023(14) 0.8350(13) 0.021(4) Uiso d . 1 . .
C C11 0.01442(13) 0.57371(11) 0.80405(10) 0.0178(2) Uani d . 1 . .
H H111 0.0795(15) 0.5338(14) 0.7556(13) 0.022(4) Uiso d . 1 . .
H H112 -0.0444(15) 0.5101(14) 0.8393(13) 0.023(4) Uiso d . 1 . .
H H113 -0.0456(15) 0.6270(15) 0.7544(14) 0.026(4) Uiso d . 1 . .
C C12 -0.00717(13) 0.70098(11) 0.98606(10) 0.0169(2) Uani d . 1 . .
H H121 0.0494(16) 0.7364(15) 1.0534(13) 0.026(4) Uiso d . 1 . .
H H122 -0.0616(15) 0.7636(14) 0.9446(13) 0.021(4) Uiso d . 1 . .
H H123 -0.0673(16) 0.6388(16) 1.0133(15) 0.035(4) Uiso d . 1 . .
C C13 0.94875(12) 0.32918(11) 0.52248(10) 0.0177(2) 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
C2 O1 C1 . . 118.66(9) ?
C4 O2 C1 . . 118.29(8) ?
N2 N1 C3 . . 120.47(10) ?
N1 N2 C5 . . 119.38(10) ?
N1 N2 H2 . . 119.3(10) ?
C5 N2 H2 . . 121.1(10) ?
O1 C1 O2 . . 109.71(9) ?
O1 C1 C11 . . 110.85(9) ?
O1 C1 C12 . . 106.43(9) ?
O2 C1 C11 . . 109.92(9) ?
O2 C1 C12 . . 105.40(9) ?
C12 C1 C11 . . 114.31(10) ?
O1 C2 C3 . . 114.85(10) ?
O4 C2 O1 . . 119.33(11) ?
O4 C2 C3 . . 125.66(11) ?
N1 C3 C2 . . 115.57(10) ?
N1 C3 C4 . . 124.16(11) ?
C4 C3 C2 . . 119.88(10) ?
O2 C4 C3 . . 116.02(10) ?
O3 C4 O2 . . 119.38(10) ?
O3 C4 C3 . . 124.52(10) ?
C6 C5 N2 . . 121.03(11) ?
C10 C5 N2 . . 117.89(10) ?
C10 C5 C6 . . 121.08(10) ?
C5 C6 H6 . . 120.9(9) ?
C7 C6 C5 . . 119.34(11) ?
C7 C6 H6 . . 119.7(9) ?
C6 C7 C8 . . 119.80(11) ?
C6 C7 H7 . . 119.6(9) ?
C8 C7 H7 . . 120.6(9) ?
C7 C8 C9 . . 120.56(10) ?
C7 C8 C13 . . 120.76(10) ?
C9 C8 C13 . . 118.68(11) ?
C8 C9 H9 . . 120.9(9) ?
C10 C9 C8 . . 119.72(11) ?
C10 C9 H9 . . 119.4(9) ?
C5 C10 H10 . . 119.5(9) ?
C9 C10 C5 . . 119.50(10) ?
C9 C10 H10 . . 121.0(9) ?
C1 C11 H111 . . 111.6(9) ?
C1 C11 H113 . . 110.4(9) ?
C1 C11 H112 . . 108.6(9) ?
H111 C11 H112 . . 109.0(12) ?
H111 C11 H113 . . 108.9(13) ?
H113 C11 H112 . . 108.3(12) ?
C1 C12 H121 . . 108.9(9) ?
C1 C12 H122 . . 107.9(8) ?
C1 C12 H123 . . 109.4(10) ?
H121 C12 H123 . . 110.0(13) ?
H122 C12 H121 . . 110.9(13) ?
H122 C12 H123 . . 109.6(13) ?
N3 C13 C8 . . 178.56(13) ?
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 . 1.4435(13) ?
O1 C2 . 1.3645(13) ?
O2 C1 . 1.4493(13) ?
O2 C4 . 1.3533(13) ?
O3 C4 . 1.2081(14) ?
O4 C2 . 1.2009(14) ?
N1 N2 . 1.3082(14) ?
N1 C3 . 1.3116(14) ?
N2 C5 . 1.4075(14) ?
N2 H2 . 0.922(17) ?
N3 C13 . 1.1473(15) ?
C1 C12 . 1.5055(15) ?
C2 C3 . 1.4812(16) ?
C3 C4 . 1.4718(15) ?
C5 C6 . 1.3981(16) ?
C5 C10 . 1.3932(17) ?
C6 C7 . 1.3878(16) ?
C6 H6 . 0.954(15) ?
C7 C8 . 1.3949(17) ?
C7 H7 . 0.974(15) ?
C8 C9 . 1.4012(16) ?
C8 C13 . 1.4418(15) ?
C9 C10 . 1.3854(15) ?
C9 H9 . 0.936(15) ?
C10 H10 . 0.986(15) ?
C11 C1 . 1.5117(16) ?
C11 H111 . 0.976(15) ?
C11 H113 . 0.984(16) ?
C11 H112 . 1.007(16) ?
C12 H122 . 0.975(15) ?
C12 H121 . 0.999(16) ?
C12 H123 . 0.967(17) ?
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
_geom_hbond_publ_flag
N2 H2 O3 . 0.92(2) 1.958(16) 2.6674(13) 132.0(10) yes
C9 H9 N1 2_646 0.94(2) 2.624(15) 3.5320(16) 164.0(10) yes
C10 H10 N3 4_566 0.99(2) 2.485(15) 3.3876(16) 152.0(10) yes
C12 H123 O2 3_567 0.97(2) 2.527(17) 3.4454(15) 159.0(10) yes
C12 H122 Cg1 2_645 0.98(2) 2.491(15) 3.4575(13) 171.0(10) yes
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 O1 C1 O2 . . . . 51.23(12) ?
C2 O1 C1 C11 . . . . -70.35(13) ?
C2 O1 C1 C12 . . . . 164.79(10) ?
C1 O1 C2 O4 . . . . 163.20(11) ?
C1 O1 C2 C3 . . . . -21.07(14) ?
C4 O2 C1 O1 . . . . -50.36(12) ?
C4 O2 C1 C12 . . . . -164.59(9) ?
C4 O2 C1 C11 . . . . 71.77(12) ?
C1 O2 C4 O3 . . . . -163.46(10) ?
C1 O2 C4 C3 . . . . 19.68(14) ?
C3 N1 N2 C5 . . . . 179.24(10) ?
N2 N1 C3 C2 . . . . 173.80(10) ?
N2 N1 C3 C4 . . . . 0.97(18) ?
N1 N2 C5 C6 . . . . -11.37(17) ?
N1 N2 C5 C10 . . . . 169.52(10) ?
O1 C2 C3 N1 . . . . 174.77(10) ?
O1 C2 C3 C4 . . . . -12.07(16) ?
O4 C2 C3 N1 . . . . -9.81(19) ?
O4 C2 C3 C4 . . . . 163.35(12) ?
N1 C3 C4 O2 . . . . -174.73(10) ?
N1 C3 C4 O3 . . . . 8.59(19) ?
C2 C3 C4 O2 . . . . 12.73(16) ?
C2 C3 C4 O3 . . . . -163.95(11) ?
N2 C5 C6 C7 . . . . -178.47(10) ?
C10 C5 C6 C7 . . . . 0.62(18) ?
N2 C5 C10 C9 . . . . 178.44(10) ?
C6 C5 C10 C9 . . . . -0.67(18) ?
C5 C6 C7 C8 . . . . 0.05(18) ?
C6 C7 C8 C9 . . . . -0.65(18) ?
C6 C7 C8 C13 . . . . 178.87(11) ?
C7 C8 C9 C10 . . . . 0.60(18) ?
C13 C8 C9 C10 . . . . -178.93(11) ?
C8 C9 C10 C5 . . . . 0.06(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745383
