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In the title mol­ecule, C9H9N3O6, all bond lengths and angles are normal. The crystal packing shows inter­molecular C—H...O hydrogen bonds, with H...O distances of 2.299 (16) and 2.374 (15) Å, which link the mol­ecules into ribbons.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680701121X/cv2200sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680701121X/cv2200Isup2.hkl
Contains datablock I

CCDC reference: 642954

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.028
  • wR factor = 0.079
  • Data-to-parameter ratio = 9.2

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95
Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 68.21 From the CIF: _diffrn_reflns_theta_full 68.21 From the CIF: _reflns_number_total 1846 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 1948 Completeness (_total/calc) 94.76% PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.95 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.23 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT142_ALERT_4_C su on b - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT143_ALERT_4_C su on c - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) . 10 Ang. PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 6 PLAT432_ALERT_2_C Short Inter X...Y Contact O2 .. C7 .. 2.93 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus-NT (Bruker, 2001); data reduction: SAINT-Plus-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-NT (Bruker, 2000); software used to prepare material for publication: SHELXTL-NT.

Dimethyl (2E)-2-(4-nitro-1H-imidazol-1-yl)but-2-enedioate top
Crystal data top
C9H9N3O6Z = 2
Mr = 255.19F(000) = 264
Triclinic, P1Dx = 1.597 Mg m3
a = 4.7704 (1) ÅCu Kα radiation, λ = 1.54178 Å
b = 10.5020 (1) ÅCell parameters from 3781 reflections
c = 11.2873 (1) Åθ = 4.1–68.2°
α = 104.931 (1)°µ = 1.19 mm1
β = 96.330 (1)°T = 100 K
γ = 100.034 (1)°Prism, colourless
V = 530.83 (1) Å30.35 × 0.30 × 0.12 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1846 independent reflections
Radiation source: fine-focus sealed tube1752 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.013
φ and ω scansθmax = 68.2°, θmin = 4.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 55
Tmin = 0.692, Tmax = 0.867k = 1212
4928 measured reflectionsl = 1313
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028All H-atom parameters refined
wR(F2) = 0.079 w = 1/[σ2(Fo2) + (0.051P)2 + 0.1508P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
1846 reflectionsΔρmax = 0.22 e Å3
200 parametersΔρmin = 0.20 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0046 (9)
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.1700 (2)0.38551 (11)0.19217 (10)0.0161 (3)
C20.3147 (2)0.50023 (11)0.17376 (10)0.0162 (3)
C30.5335 (3)0.44767 (11)0.33258 (11)0.0175 (3)
C40.7794 (2)0.65440 (11)0.28152 (10)0.0152 (2)
C50.8180 (2)0.71553 (11)0.19278 (10)0.0165 (3)
C61.0720 (2)0.82595 (11)0.20908 (10)0.0160 (3)
C71.2768 (3)1.00387 (12)0.13513 (12)0.0204 (3)
C80.9775 (2)0.69715 (11)0.40549 (10)0.0160 (3)
C91.1740 (3)0.87724 (14)0.58268 (12)0.0268 (3)
N10.0990 (2)0.30561 (9)0.11932 (9)0.0169 (2)
N20.3031 (2)0.35152 (10)0.28957 (9)0.0183 (2)
N30.5529 (2)0.54118 (9)0.26479 (8)0.0150 (2)
O10.21413 (19)0.34984 (9)0.03896 (8)0.0221 (2)
O20.20049 (19)0.19975 (8)0.13956 (8)0.0232 (2)
O31.03086 (18)0.89764 (8)0.12910 (7)0.0187 (2)
O41.29029 (18)0.84583 (9)0.28240 (8)0.0226 (2)
O50.96040 (18)0.81862 (8)0.47006 (7)0.0201 (2)
O61.12434 (18)0.62581 (8)0.43763 (7)0.0208 (2)
H20.271 (3)0.5458 (15)0.1152 (14)0.023 (4)*
H30.676 (3)0.4536 (14)0.4001 (14)0.020 (3)*
H50.685 (3)0.6901 (14)0.1131 (14)0.018 (3)*
H7A1.296 (3)1.0735 (16)0.2121 (15)0.027 (4)*
H7B1.444 (4)0.9654 (16)0.1266 (15)0.028 (4)*
H7C1.227 (3)1.0362 (15)0.0662 (14)0.023 (4)*
H9A1.139 (4)0.8318 (18)0.6427 (17)0.041 (5)*
H9B1.159 (4)0.9681 (18)0.6085 (16)0.033 (4)*
H9C1.365 (4)0.8709 (17)0.5631 (16)0.035 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0155 (6)0.0172 (5)0.0148 (5)0.0019 (4)0.0024 (4)0.0040 (4)
C20.0158 (6)0.0186 (6)0.0144 (5)0.0036 (4)0.0021 (4)0.0055 (4)
C30.0189 (6)0.0188 (6)0.0158 (5)0.0034 (4)0.0015 (5)0.0072 (4)
C40.0135 (6)0.0152 (5)0.0169 (5)0.0036 (4)0.0026 (4)0.0041 (4)
C50.0155 (6)0.0177 (6)0.0156 (6)0.0024 (4)0.0007 (4)0.0051 (4)
C60.0170 (6)0.0170 (6)0.0143 (5)0.0036 (4)0.0038 (5)0.0044 (4)
C70.0196 (6)0.0183 (6)0.0222 (6)0.0025 (5)0.0020 (5)0.0089 (5)
C80.0151 (6)0.0182 (6)0.0150 (5)0.0001 (4)0.0034 (4)0.0069 (4)
C90.0341 (8)0.0237 (7)0.0163 (6)0.0000 (5)0.0044 (5)0.0023 (5)
N10.0169 (5)0.0182 (5)0.0148 (5)0.0012 (4)0.0037 (4)0.0043 (4)
N20.0191 (5)0.0186 (5)0.0176 (5)0.0022 (4)0.0025 (4)0.0073 (4)
N30.0145 (5)0.0157 (5)0.0143 (5)0.0012 (4)0.0015 (4)0.0053 (4)
O10.0212 (5)0.0253 (5)0.0194 (4)0.0024 (3)0.0017 (3)0.0092 (3)
O20.0241 (5)0.0206 (4)0.0225 (5)0.0041 (3)0.0034 (4)0.0080 (3)
O30.0170 (4)0.0192 (4)0.0197 (4)0.0012 (3)0.0003 (3)0.0096 (3)
O40.0174 (5)0.0273 (5)0.0225 (4)0.0005 (3)0.0014 (4)0.0112 (4)
O50.0247 (5)0.0183 (4)0.0154 (4)0.0032 (3)0.0003 (3)0.0033 (3)
O60.0209 (5)0.0222 (4)0.0199 (4)0.0047 (3)0.0003 (3)0.0081 (3)
Geometric parameters (Å, º) top
C1—C21.3571 (16)C6—O31.3353 (14)
C1—N21.3661 (15)C7—O31.4535 (14)
C1—N11.4366 (15)C7—H7A0.964 (17)
C2—N31.3699 (15)C7—H7B0.960 (17)
C2—H20.937 (16)C7—H7C0.949 (16)
C3—N21.3062 (15)C8—O61.2045 (14)
C3—N31.3892 (15)C8—O51.3172 (14)
C3—H30.944 (16)C9—O51.4578 (15)
C4—C51.3343 (16)C9—H9A0.937 (19)
C4—N31.4172 (15)C9—H9B0.942 (18)
C4—C81.5129 (16)C9—H9C0.970 (18)
C5—C61.4827 (16)N1—O21.2208 (13)
C5—H50.986 (15)N1—O11.2394 (13)
C6—O41.2074 (15)
C2—C1—N2113.53 (10)O3—C7—H7C104.5 (9)
C2—C1—N1124.78 (10)H7A—C7—H7C110.7 (13)
N2—C1—N1121.68 (10)H7B—C7—H7C110.6 (13)
C1—C2—N3104.03 (10)O6—C8—O5126.61 (10)
C1—C2—H2130.9 (9)O6—C8—C4122.68 (10)
N3—C2—H2125.1 (10)O5—C8—C4110.70 (9)
N2—C3—N3112.07 (10)O5—C9—H9A111.4 (11)
N2—C3—H3125.3 (9)O5—C9—H9B104.4 (10)
N3—C3—H3122.6 (9)H9A—C9—H9B113.0 (15)
C5—C4—N3122.10 (10)O5—C9—H9C109.6 (10)
C5—C4—C8123.00 (10)H9A—C9—H9C108.1 (15)
N3—C4—C8114.87 (9)H9B—C9—H9C110.3 (15)
C4—C5—C6120.67 (11)O2—N1—O1124.03 (10)
C4—C5—H5123.2 (8)O2—N1—C1118.96 (10)
C6—C5—H5116.1 (8)O1—N1—C1117.01 (9)
O4—C6—O3124.54 (11)C3—N2—C1103.58 (9)
O4—C6—C5124.46 (11)C2—N3—C3106.79 (10)
O3—C6—C5110.96 (10)C2—N3—C4125.78 (10)
O3—C7—H7A108.2 (10)C3—N3—C4127.38 (10)
O3—C7—H7B108.8 (10)C6—O3—C7114.25 (9)
H7A—C7—H7B113.5 (13)C8—O5—C9114.86 (10)
N2—C1—C2—N30.03 (13)C2—C1—N2—C30.40 (13)
N1—C1—C2—N3179.28 (10)N1—C1—N2—C3178.93 (10)
N3—C4—C5—C6174.53 (9)C1—C2—N3—C30.34 (11)
C8—C4—C5—C63.54 (17)C1—C2—N3—C4177.20 (10)
C4—C5—C6—O419.57 (17)N2—C3—N3—C20.64 (13)
C4—C5—C6—O3162.47 (10)N2—C3—N3—C4176.86 (10)
C5—C4—C8—O6115.07 (13)C5—C4—N3—C215.99 (17)
N3—C4—C8—O663.12 (14)C8—C4—N3—C2165.80 (10)
C5—C4—C8—O565.79 (14)C5—C4—N3—C3161.05 (11)
N3—C4—C8—O5116.02 (10)C8—C4—N3—C317.16 (15)
C2—C1—N1—O2175.51 (10)O4—C6—O3—C70.87 (16)
N2—C1—N1—O25.23 (16)C5—C6—O3—C7177.09 (9)
C2—C1—N1—O14.57 (16)O6—C8—O5—C99.68 (16)
N2—C1—N1—O1174.68 (9)C4—C8—O5—C9171.23 (10)
N3—C3—N2—C10.62 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O1i0.936 (16)2.299 (16)3.2298 (15)172.7 (13)
C3—H3···O6ii0.945 (15)2.374 (15)3.2440 (15)152.9 (13)
Symmetry codes: (i) x, y+1, z; (ii) x+2, y+1, z+1.
 

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