#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/17/8101753.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8101753
loop_
_publ_author_name
'M. D. Crozet'
'M. Giorgi'
'T. Terme'
'P. Vanelle'
_publ_section_title
;
Crystal structure of diethyl 2-(1-methyl-5-nitro-1H-imidazol-4-ylmethylene)
malonate, C₁₂H₁₅N₃O₆
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              217
_journal_page_last               218
_journal_volume                  220
_journal_year                    2005
_chemical_formula_moiety         'C12 H15 N3 O6'
_chemical_formula_sum            'C12 H15 N3 O6'
_chemical_formula_weight         297.27
_chemical_name_systematic
'diethyl 2-(1-methyl-5-nitro-1H-imidazol-4-ylmethylene)malonate'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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
_cell_angle_alpha                90.
_cell_angle_beta                 93.8120(10)
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   14.7940(7)
_cell_length_b                   5.46100(10)
_cell_length_c                   18.0420(9)
_cell_measurement_reflns_used    3006
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.32
_cell_measurement_theta_min      1.
_cell_volume                     1454.39(10)
_computing_cell_refinement
'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD (Bruker-Nonius, 1998)'
_computing_data_reduction
'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.909
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       phi
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.054
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8345
_diffrn_reflns_theta_full        25.8
_diffrn_reflns_theta_max         25.8
_diffrn_reflns_theta_min         3.45
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          .4
_exptl_crystal_size_mid          .3
_exptl_crystal_size_min          .3
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.029
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2692
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0453
_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)+(0.0569P)²+0.4245P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1206
_reflns_number_gt                2311
_reflns_number_total             2692
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-1495.cff
_cod_data_source_block           malo1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' 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 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'geom and difmap' was changed
to 'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               8101753
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O8 O 0.44994(9) -0.2344(3) 0.76944(7) 0.0658(4) Uani 1 4 e d . . .
O9 O 0.33564(10) -0.0029(3) 0.73796(7) 0.0723(4) Uani 1 4 e d . . .
O13 O 0.30392(8) 0.8386(2) 0.96799(7) 0.0556(3) Uani 1 4 e d . . .
O14 O 0.22277(8) 0.5023(2) 0.99027(6) 0.0504(3) Uani 1 4 e d . . .
O18 O 0.14402(10) 0.6481(3) 0.76165(8) 0.0806(5) Uani 1 4 e d . . .
O19 O 0.12951(8) 0.8636(3) 0.86533(7) 0.0645(4) Uani 1 4 e d . . .
N2 N 0.42245(9) 0.3833(3) 0.92898(7) 0.0436(3) Uani 1 4 e d . . .
N4 N 0.49909(8) 0.0655(2) 0.88783(7) 0.0392(3) Uani 1 4 e d . . .
N7 N 0.40212(10) -0.0552(3) 0.77891(7) 0.0477(4) Uani 1 4 e d . . .
C1 C 0.37683(10) 0.2976(3) 0.86602(8) 0.0392(3) Uani 1 4 e d . . .
C3 C 0.49444(10) 0.2424(3) 0.93948(8) 0.0416(4) Uani 1 4 e d . . .
H3 H 0.5410 0.2538 0.9790 0.050 Uiso 1 4 e d R . .
C5 C 0.57559(12) -0.1035(3) 0.88404(10) 0.0520(4) Uani 1 4 e d . . .
H5A H 0.5641 -0.2120 0.8427 0.062 Uiso 0.50 4 e d PR . .
H5B H 0.5824 -0.1972 0.9291 0.062 Uiso 0.50 4 e d PR . .
H5C H 0.6301 -0.0128 0.8778 0.062 Uiso 0.50 4 e d PR . .
H5D H 0.6171 -0.0528 0.9316 0.062 Uiso 0.50 4 e d PR . .
H5E H 0.6051 -0.0691 0.8320 0.062 Uiso 0.50 4 e d PR . .
H5F H 0.5526 -0.2979 0.8886 0.062 Uiso 0.50 4 e d PR . .
C6 C 0.42397(10) 0.1002(3) 0.84041(8) 0.0386(3) Uani 1 4 e d . . .
C10 C 0.29600(10) 0.4162(3) 0.83377(9) 0.0448(4) Uani 1 4 e d . . .
H10 H 0.2745 0.3783 0.7837 0.054 Uiso 1 4 e d R . .
C11 C 0.24685(10) 0.5819(3) 0.86736(9) 0.0446(4) Uani 1 4 e d . . .
C12 C 0.26311(10) 0.6595(3) 0.94678(9) 0.0423(4) Uani 1 4 e d . . .
C15 C 0.22934(13) 0.5520(4) 1.06940(10) 0.0592(5) Uani 1 4 e d . . .
H15A H 0.2921 0.5517 1.0868 0.071 Uiso 1 4 e d R . .
H15B H 0.2036 0.7100 1.0781 0.071 Uiso 1 4 e d R . .
C16 C 0.17818(17) 0.3570(5) 1.10560(13) 0.0805(7) Uani 1 4 e d . . .
H16A H 0.1803 0.3798 1.1584 0.097 Uiso 1 4 e d R . .
H16B H 0.2048 0.2020 1.0946 0.097 Uiso 1 4 e d R . .
H16C H 0.1163 0.3603 1.0859 0.097 Uiso 1 4 e d R . .
C17 C 0.16864(11) 0.6984(4) 0.82421(10) 0.0533(4) Uani 1 4 e d . . .
C20 C 0.05505(14) 1.0032(5) 0.83011(13) 0.0786(7) Uani 1 4 e d . . .
H20A H 0.0766 1.0930 0.7891 0.094 Uiso 1 4 e d R . .
H20B H 0.0088 0.8906 0.8122 0.094 Uiso 1 4 e d R . .
C21 C 0.02142(16) 1.1700(5) 0.88523(15) 0.0901(8) Uani 1 4 e d . . .
H21A H -0.0284 1.2659 0.8645 0.108 Uiso 1 4 e d R . .
H21B H 0.0698 1.2767 0.9027 0.108 Uiso 1 4 e d R . .
H21C H 0.0020 1.0743 0.9259 0.108 Uiso 1 4 e d R . .
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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O14 C15 117.15(14) . . ?
C17 O19 C20 117.37(15) . . ?
C3 N2 C1 105.63(13) . . ?
C3 N4 C6 104.87(12) . . ?
C3 N4 C5 123.98(13) . . ?
C6 N4 C5 130.90(13) . . ?
O9 N7 O8 123.36(14) . . ?
O9 N7 C6 117.74(15) . . ?
O8 N7 C6 118.90(14) . . ?
N2 C1 C6 108.28(13) . . ?
N2 C1 C10 122.03(14) . . ?
C6 C1 C10 129.59(14) . . ?
N2 C3 N4 113.41(13) . . ?
N2 C3 H3 127.0 . . ?
N4 C3 H3 119.6 . . ?
N4 C5 H5A 109.1 . . ?
N4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.4 . . ?
N4 C5 H5C 109.7 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N4 C5 H5D 101.9 . . ?
H5A C5 H5D 148.8 . . ?
H5B C5 H5D 55.3 . . ?
H5C C5 H5D 60.9 . . ?
N4 C5 H5E 106.8 . . ?
H5A C5 H5E 59.4 . . ?
H5B C5 H5E 143.6 . . ?
H5C C5 H5E 54.2 . . ?
H5D C5 H5E 114.4 . . ?
N4 C5 H5F 110.8 . . ?
H5A C5 H5F 55.4 . . ?
H5B C5 H5F 56.5 . . ?
H5C C5 H5F 139.5 . . ?
H5D C5 H5F 110.6 . . ?
H5E C5 H5F 111.8 . . ?
N4 C6 C1 107.80(12) . . ?
N4 C6 N7 122.67(14) . . ?
C1 C6 N7 129.48(14) . . ?
C11 C10 C1 125.63(14) . . ?
C11 C10 H10 114.7 . . ?
C1 C10 H10 119.7 . . ?
C10 C11 C17 118.68(15) . . ?
C10 C11 C12 124.73(14) . . ?
C17 C11 C12 116.58(15) . . ?
O13 C12 O14 125.05(15) . . ?
O13 C12 C11 125.58(16) . . ?
O14 C12 C11 109.35(14) . . ?
O14 C15 C16 107.24(17) . . ?
O14 C15 H15A 108.8 . . ?
C16 C15 H15A 111.4 . . ?
O14 C15 H15B 109.2 . . ?
C16 C15 H15B 110.7 . . ?
H15A C15 H15B 109.5 . . ?
C15 C16 H16A 111.1 . . ?
C15 C16 H16B 108.3 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.0 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O18 C17 O19 124.63(16) . . ?
O18 C17 C11 124.85(18) . . ?
O19 C17 C11 110.52(14) . . ?
O19 C20 C21 108.22(18) . . ?
O19 C20 H20A 109.0 . . ?
C21 C20 H20A 110.6 . . ?
O19 C20 H20B 108.3 . . ?
C21 C20 H20B 111.2 . . ?
H20A C20 H20B 109.5 . . ?
C20 C21 H21A 111.3 . . ?
C20 C21 H21B 108.8 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 108.3 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O8 N7 1.2262(19) . ?
O9 N7 1.2239(19) . ?
O13 C12 1.199(2) . ?
O14 C12 1.331(2) . ?
O14 C15 1.450(2) . ?
O18 C17 1.195(2) . ?
O19 C17 1.325(2) . ?
O19 C20 1.451(2) . ?
N2 C3 1.318(2) . ?
N2 C1 1.3650(19) . ?
N4 C3 1.347(2) . ?
N4 C6 1.3698(19) . ?
N4 C5 1.466(2) . ?
N7 C6 1.417(2) . ?
C1 C6 1.380(2) . ?
C1 C10 1.448(2) . ?
C3 H3 0.9600 . ?
C5 H5A 0.9592 . ?
C5 H5B 0.9597 . ?
C5 H5C 0.9595 . ?
C5 H5D 1.0579 . ?
C5 H5E 1.0784 . ?
C5 H5F 1.1193 . ?
C10 C11 1.331(2) . ?
C10 H10 0.9600 . ?
C11 C17 1.493(2) . ?
C11 C12 1.498(2) . ?
C15 C16 1.483(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C16 H16A 0.9598 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C20 C21 1.460(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C21 H21A 0.9599 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C3 H3 N2 3_667 0.96 2.62 3.307(2) 128.9
C5 H5D O13 3_667 1.06 2.39 3.430(2) 165.7
