#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/28/2212831.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_2212831
loop_
_publ_author_name
'Pérez-Mayoral, E.'
'Soriano, E.'
'Pacheco-Torres, J.'
'Ballesteros, P.'
_publ_section_title
;
 Dimethyl
 (2E)-2-(4-nitro-1H-imidazol-1-yl)but-2-enedioate
;
_journal_coeditor_code           CV2200
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1790
_journal_page_last               o1791
_journal_paper_doi               10.1107/S160053680701121X
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C9 H9 N3 O6'
_chemical_formula_moiety         'C9 H9 N3 O6'
_chemical_formula_sum            'C9 H9 N3 O6'
_chemical_formula_weight         255.19
_chemical_name_systematic
;
Dimethyl (2E)-2-(4-nitro-1H-imidazol-1-yl)but-2-enedioate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.9310(10)
_cell_angle_beta                 96.3300(10)
_cell_angle_gamma                100.0340(10)
_cell_formula_units_Z            2
_cell_length_a                   4.77040(10)
_cell_length_b                   10.50200(10)
_cell_length_c                   11.28730(10)
_cell_measurement_reflns_used    3781
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.217
_cell_measurement_theta_min      4.108
_cell_volume                     530.829(14)
_computing_cell_refinement       'SAINT-Plus-NT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT-Plus-NT
_computing_molecular_graphics    'SHELXTL-NT  (Bruker, 2000)'
_computing_publication_material  SHELXTL-NT
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0126
_diffrn_reflns_av_sigmaI/netI    0.0148
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4928
_diffrn_reflns_theta_full        68.21
_diffrn_reflns_theta_max         68.21
_diffrn_reflns_theta_min         4.11
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.190
_exptl_absorpt_correction_T_max  0.867
_exptl_absorpt_correction_T_min  0.692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.201
_refine_ls_extinction_coef       0.0046(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         1846
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0282
_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)+(0.051P)²+0.1508P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0792
_reflns_number_gt                1752
_reflns_number_total             1846
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2200.cif
_cod_data_source_block           I
_cod_original_cell_volume        530.828(13)
_cod_database_code               2212831
_cod_database_fobs_code          2212831
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_occupancy
C C1 0.1700(2) 0.38551(11) 0.19217(10) 0.0161(3) Uani d 1
C C2 0.3147(2) 0.50023(11) 0.17376(10) 0.0162(3) Uani d 1
C C3 0.5335(3) 0.44767(11) 0.33258(11) 0.0175(3) Uani d 1
C C4 0.7794(2) 0.65440(11) 0.28152(10) 0.0152(2) Uani d 1
C C5 0.8180(2) 0.71553(11) 0.19278(10) 0.0165(3) Uani d 1
C C6 1.0720(2) 0.82595(11) 0.20908(10) 0.0160(3) Uani d 1
C C7 1.2768(3) 1.00387(12) 0.13513(12) 0.0204(3) Uani d 1
C C8 0.9775(2) 0.69715(11) 0.40549(10) 0.0160(3) Uani d 1
C C9 1.1740(3) 0.87724(14) 0.58268(12) 0.0268(3) Uani d 1
N N1 -0.0990(2) 0.30561(9) 0.11932(9) 0.0169(2) Uani d 1
N N2 0.3031(2) 0.35152(10) 0.28957(9) 0.0183(2) Uani d 1
N N3 0.5529(2) 0.54118(9) 0.26479(8) 0.0150(2) Uani d 1
O O1 -0.21413(19) 0.34984(9) 0.03896(8) 0.0221(2) Uani d 1
O O2 -0.20049(19) 0.19975(8) 0.13956(8) 0.0232(2) Uani d 1
O O3 1.03086(18) 0.89764(8) 0.12910(7) 0.0187(2) Uani d 1
O O4 1.29029(18) 0.84583(9) 0.28240(8) 0.0226(2) Uani d 1
O O5 0.96040(18) 0.81862(8) 0.47006(7) 0.0201(2) Uani d 1
O O6 1.12434(18) 0.62581(8) 0.43763(7) 0.0208(2) Uani d 1
H H2 0.271(3) 0.5458(15) 0.1152(14) 0.023(4) Uiso d 1
H H3 0.676(3) 0.4536(14) 0.4001(14) 0.020(3) Uiso d 1
H H5 0.685(3) 0.6901(14) 0.1131(14) 0.018(3) Uiso d 1
H H7A 1.296(3) 1.0735(16) 0.2121(15) 0.027(4) Uiso d 1
H H7B 1.444(4) 0.9654(16) 0.1266(15) 0.028(4) Uiso d 1
H H7C 1.227(3) 1.0362(15) 0.0662(14) 0.023(4) Uiso d 1
H H9A 1.139(4) 0.8318(18) 0.6427(17) 0.041(5) Uiso d 1
H H9B 1.159(4) 0.9681(18) 0.6085(16) 0.033(4) Uiso d 1
H H9C 1.365(4) 0.8709(17) 0.5631(16) 0.035(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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C2 C1 N2 113.53(10)
C2 C1 N1 124.78(10)
N2 C1 N1 121.68(10)
C1 C2 N3 104.03(10)
C1 C2 H2 130.9(9)
N3 C2 H2 125.1(10)
N2 C3 N3 112.07(10)
N2 C3 H3 125.3(9)
N3 C3 H3 122.6(9)
C5 C4 N3 122.10(10)
C5 C4 C8 123.00(10)
N3 C4 C8 114.87(9)
C4 C5 C6 120.67(11)
C4 C5 H5 123.2(8)
C6 C5 H5 116.1(8)
O4 C6 O3 124.54(11)
O4 C6 C5 124.46(11)
O3 C6 C5 110.96(10)
O3 C7 H7A 108.2(10)
O3 C7 H7B 108.8(10)
H7A C7 H7B 113.5(13)
O3 C7 H7C 104.5(9)
H7A C7 H7C 110.7(13)
H7B C7 H7C 110.6(13)
O6 C8 O5 126.61(10)
O6 C8 C4 122.68(10)
O5 C8 C4 110.70(9)
O5 C9 H9A 111.4(11)
O5 C9 H9B 104.4(10)
H9A C9 H9B 113.0(15)
O5 C9 H9C 109.6(10)
H9A C9 H9C 108.1(15)
H9B C9 H9C 110.3(15)
O2 N1 O1 124.03(10)
O2 N1 C1 118.96(10)
O1 N1 C1 117.01(9)
C3 N2 C1 103.58(9)
C2 N3 C3 106.79(10)
C2 N3 C4 125.78(10)
C3 N3 C4 127.38(10)
C6 O3 C7 114.25(9)
C8 O5 C9 114.86(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.3571(16)
C1 N2 1.3661(15)
C1 N1 1.4366(15)
C2 N3 1.3699(15)
C2 H2 0.937(16)
C3 N2 1.3062(15)
C3 N3 1.3892(15)
C3 H3 0.944(16)
C4 C5 1.3343(16)
C4 N3 1.4172(15)
C4 C8 1.5129(16)
C5 C6 1.4827(16)
C5 H5 0.986(15)
C6 O4 1.2074(15)
C6 O3 1.3353(14)
C7 O3 1.4535(14)
C7 H7A 0.964(17)
C7 H7B 0.960(17)
C7 H7C 0.949(16)
C8 O6 1.2045(14)
C8 O5 1.3172(14)
C9 O5 1.4578(15)
C9 H9A 0.937(19)
C9 H9B 0.942(18)
C9 H9C 0.970(18)
N1 O2 1.2208(13)
N1 O1 1.2394(13)
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
C2 H2 O1 2_565 0.936(16) 2.299(16) 3.2298(15) 172.7(13) yes
C3 H3 O6 2_766 0.945(15) 2.374(15) 3.2440(15) 152.9(13) 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
N2 C1 C2 N3 -0.03(13)
N1 C1 C2 N3 179.28(10)
N3 C4 C5 C6 -174.53(9)
C8 C4 C5 C6 3.54(17)
C4 C5 C6 O4 19.57(17)
C4 C5 C6 O3 -162.47(10)
C5 C4 C8 O6 -115.07(13)
N3 C4 C8 O6 63.12(14)
C5 C4 C8 O5 65.79(14)
N3 C4 C8 O5 -116.02(10)
C2 C1 N1 O2 175.51(10)
N2 C1 N1 O2 -5.23(16)
C2 C1 N1 O1 -4.57(16)
N2 C1 N1 O1 174.68(9)
N3 C3 N2 C1 -0.62(12)
C2 C1 N2 C3 0.40(13)
N1 C1 N2 C3 -178.93(10)
C1 C2 N3 C3 -0.34(11)
C1 C2 N3 C4 177.20(10)
N2 C3 N3 C2 0.64(13)
N2 C3 N3 C4 -176.86(10)
C5 C4 N3 C2 -15.99(17)
C8 C4 N3 C2 165.80(10)
C5 C4 N3 C3 161.05(11)
C8 C4 N3 C3 -17.16(15)
O4 C6 O3 C7 0.87(16)
C5 C6 O3 C7 -177.09(9)
O6 C8 O5 C9 9.68(16)
C4 C8 O5 C9 -171.23(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21185385
