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In the title hydrated molecular salt, 2C4H8N3O+·C8H3NO62−·H2O, the dihedral angles between the benzene ring and the nitro group and the carboxylate groups are 48.0 (2), 55.3 (2) and 60.7 (2)°, respectively. In the crystal, the components are linked by N—H...O, O—H...O and C—H...O hydrogen bonds, generating a two-dimensional network parallel to (102).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314616009895/sj4041sup1.cif
Contains datablocks C3NP, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314616009895/sj4041Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314616009895/sj4041Isup3.cml
Supplementary material

CCDC reference: 1486234

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.034
  • wR factor = 0.097
  • Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.595 2 Report
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 3 Note PLAT005_ALERT_5_G No Embedded Refinement Details found in the CIF Please Do ! PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 6 Report PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings Differ Please Check PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 2 Note PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd. # 4 Note H2 O PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 3 Note PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still 74 % PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min) 1 Note PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF .... 1 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density 6 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 1 ALERT level C = Check. Ensure it is not caused by an omission or oversight 12 ALERT level G = General information/check it is not something unexpected 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 2 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Bis(2-amino-1-methyl-4-oxo-1H-imidazol-3-ium) 3-nitrobenzene-1,2-dioate monohydrate top
Crystal data top
2C4H8N3O+·C8H3NO62·H2OF(000) = 952
Mr = 455.40Dx = 1.471 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3032 reflections
a = 7.6682 (3) Åθ = 2.5–25.0°
b = 16.5504 (6) ŵ = 0.12 mm1
c = 16.2358 (7) ÅT = 295 K
β = 93.775 (1)°Block, colourless
V = 2056.04 (14) Å30.30 × 0.25 × 0.20 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer
3620 independent reflections
Radiation source: fine-focus sealed tube3202 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
Detector resolution: 0 pixels mm-1θmax = 25.0°, θmin = 2.5°
ω and φ scansh = 99
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1919
Tmin = 0.964, Tmax = 0.975l = 1919
30566 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0511P)2 + 0.6212P]
where P = (Fo2 + 2Fc2)/3
3620 reflections(Δ/σ)max < 0.001
299 parametersΔρmax = 0.23 e Å3
3 restraintsΔρmin = 0.19 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O40.31739 (13)0.24338 (6)0.37689 (7)0.0426 (3)
O20.20496 (15)0.39851 (6)0.44152 (7)0.0468 (3)
O10.05094 (16)0.36012 (6)0.33692 (7)0.0500 (3)
O70.12906 (18)0.00022 (8)0.32383 (8)0.0623 (4)
O30.26695 (14)0.34371 (6)0.46389 (7)0.0455 (3)
O80.37908 (18)0.23485 (8)0.30455 (8)0.0650 (4)
N40.04747 (17)0.14441 (7)0.19650 (8)0.0411 (3)
N50.50199 (16)0.15212 (7)0.21091 (8)0.0382 (3)
H50.54310.18820.17940.046*
C10.09432 (17)0.26573 (8)0.44182 (8)0.0292 (3)
C50.08351 (17)0.15554 (8)0.48841 (8)0.0306 (3)
O60.36494 (17)0.16305 (9)0.54522 (9)0.0698 (4)
N10.25658 (17)0.12099 (8)0.50719 (9)0.0455 (3)
N70.43615 (16)0.03075 (8)0.25712 (7)0.0392 (3)
N20.15811 (18)0.06240 (8)0.09368 (8)0.0446 (3)
H2A0.19820.10280.06750.054*
H2B0.17110.01410.07550.054*
C60.07245 (17)0.23258 (7)0.45540 (7)0.0275 (3)
N60.59974 (16)0.04045 (7)0.13985 (8)0.0406 (3)
H6A0.60650.01110.13430.049*
H6B0.64790.07180.10570.049*
N30.01716 (15)0.01224 (7)0.20550 (7)0.0367 (3)
H3A0.02750.03800.19320.044*
O50.28472 (18)0.05264 (8)0.48399 (11)0.0811 (5)
C20.24056 (18)0.22093 (9)0.45977 (9)0.0357 (3)
H20.35120.24360.45130.043*
C140.07773 (18)0.07435 (8)0.16086 (8)0.0341 (3)
C40.05969 (19)0.11000 (8)0.50609 (9)0.0364 (3)
H40.04640.05840.52820.044*
C80.23328 (17)0.27727 (8)0.43044 (8)0.0314 (3)
C30.22333 (19)0.14322 (9)0.49004 (9)0.0387 (3)
H30.32240.11320.49970.046*
C70.11757 (18)0.34859 (8)0.40421 (9)0.0338 (3)
C90.3674 (2)0.08763 (10)0.31486 (9)0.0468 (4)
H9A0.24200.08150.31720.056*
H9B0.42290.08070.36980.056*
C110.51691 (17)0.07093 (8)0.19967 (8)0.0333 (3)
C100.4126 (2)0.16844 (10)0.27923 (10)0.0445 (4)
C130.0626 (2)0.04049 (10)0.27279 (9)0.0423 (4)
C150.4564 (2)0.05471 (10)0.27549 (11)0.0492 (4)
H15A0.55080.06210.31660.074*
H15B0.35020.07520.29580.074*
H15C0.48140.08330.22620.074*
C120.0482 (2)0.13135 (10)0.26946 (10)0.0480 (4)
H12A0.16270.15640.26380.058*
H12B0.01550.15240.31850.058*
C160.0946 (3)0.22366 (10)0.16828 (11)0.0602 (5)
H16A0.19490.21950.13610.090*
H16B0.12170.25800.21500.090*
H16C0.00130.24620.13490.090*
O9W0.3299 (2)0.38052 (7)0.59774 (8)0.0656 (4)
H9WA0.302 (3)0.3802 (13)0.5476 (7)0.090 (8)*
H9WB0.358 (3)0.3319 (8)0.6078 (13)0.100 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O40.0439 (6)0.0355 (5)0.0506 (6)0.0020 (4)0.0200 (5)0.0028 (5)
O20.0563 (7)0.0333 (6)0.0528 (6)0.0121 (5)0.0187 (5)0.0086 (5)
O10.0735 (8)0.0375 (6)0.0411 (6)0.0100 (5)0.0192 (5)0.0112 (5)
O70.0802 (9)0.0622 (8)0.0472 (7)0.0035 (7)0.0254 (6)0.0062 (6)
O30.0558 (7)0.0379 (6)0.0445 (6)0.0188 (5)0.0165 (5)0.0095 (5)
O80.0799 (9)0.0548 (8)0.0619 (8)0.0041 (6)0.0164 (7)0.0222 (6)
N40.0553 (8)0.0328 (6)0.0353 (7)0.0030 (5)0.0038 (6)0.0046 (5)
N50.0414 (7)0.0341 (7)0.0400 (7)0.0036 (5)0.0093 (5)0.0023 (5)
C10.0342 (7)0.0271 (7)0.0267 (6)0.0014 (5)0.0042 (5)0.0002 (5)
C50.0335 (7)0.0272 (7)0.0317 (7)0.0031 (5)0.0064 (5)0.0003 (5)
O60.0455 (7)0.0771 (9)0.0840 (10)0.0088 (7)0.0164 (7)0.0045 (8)
N10.0419 (7)0.0367 (7)0.0590 (8)0.0083 (6)0.0114 (6)0.0131 (6)
N70.0424 (7)0.0408 (7)0.0352 (6)0.0059 (5)0.0086 (5)0.0018 (5)
N20.0640 (9)0.0340 (7)0.0374 (7)0.0006 (6)0.0153 (6)0.0025 (5)
C60.0337 (7)0.0244 (6)0.0247 (6)0.0016 (5)0.0049 (5)0.0023 (5)
N60.0464 (7)0.0322 (6)0.0452 (7)0.0007 (5)0.0177 (6)0.0027 (5)
N30.0438 (7)0.0333 (6)0.0334 (6)0.0011 (5)0.0052 (5)0.0034 (5)
O50.0613 (8)0.0378 (7)0.1471 (15)0.0172 (6)0.0299 (9)0.0047 (8)
C20.0308 (7)0.0379 (8)0.0388 (8)0.0019 (6)0.0050 (6)0.0017 (6)
C140.0377 (7)0.0343 (7)0.0298 (7)0.0011 (6)0.0026 (6)0.0021 (6)
C40.0458 (8)0.0231 (6)0.0418 (8)0.0001 (6)0.0133 (6)0.0031 (6)
C80.0330 (7)0.0298 (7)0.0317 (7)0.0012 (5)0.0037 (5)0.0018 (5)
C30.0374 (8)0.0354 (8)0.0445 (8)0.0078 (6)0.0130 (6)0.0005 (6)
C70.0357 (7)0.0311 (7)0.0344 (7)0.0015 (6)0.0023 (6)0.0048 (6)
C90.0486 (9)0.0593 (10)0.0334 (8)0.0110 (8)0.0093 (7)0.0081 (7)
C110.0293 (7)0.0360 (7)0.0347 (7)0.0029 (5)0.0020 (5)0.0006 (6)
C100.0438 (9)0.0494 (9)0.0404 (8)0.0025 (7)0.0039 (7)0.0123 (7)
C130.0460 (8)0.0488 (9)0.0322 (8)0.0065 (7)0.0036 (6)0.0006 (7)
C150.0487 (9)0.0476 (9)0.0517 (9)0.0067 (7)0.0064 (7)0.0135 (8)
C120.0629 (10)0.0468 (9)0.0350 (8)0.0098 (8)0.0073 (7)0.0077 (7)
C160.0952 (15)0.0345 (9)0.0512 (10)0.0020 (9)0.0069 (9)0.0022 (7)
O9W0.1076 (11)0.0374 (7)0.0546 (8)0.0013 (7)0.0266 (8)0.0016 (6)
Geometric parameters (Å, º) top
O4—C81.2491 (16)C6—C81.5159 (18)
O2—C71.2458 (17)N6—C111.2970 (18)
O1—C71.2508 (17)N6—H6A0.8600
O7—C131.2065 (19)N6—H6B0.8600
O3—C81.2459 (17)N3—C141.3573 (19)
O8—C101.2072 (19)N3—C131.3690 (19)
N4—C141.3232 (18)N3—H3A0.8600
N4—C161.443 (2)C2—C31.380 (2)
N4—C121.450 (2)C2—H20.9300
N5—C111.3617 (18)C4—C31.379 (2)
N5—C101.369 (2)C4—H40.9300
N5—H50.8600C3—H30.9300
C1—C21.3911 (19)C9—C101.507 (2)
C1—C61.3957 (18)C9—H9A0.9700
C1—C71.5070 (18)C9—H9B0.9700
C5—C41.3775 (19)C13—C121.509 (2)
C5—C61.3836 (18)C15—H15A0.9600
C5—N11.4587 (18)C15—H15B0.9600
O6—N11.2200 (19)C15—H15C0.9600
N1—O51.2161 (18)C12—H12A0.9700
N7—C111.3311 (18)C12—H12B0.9700
N7—C151.452 (2)C16—H16A0.9600
N7—C91.452 (2)C16—H16B0.9600
N2—C141.3028 (19)C16—H16C0.9600
N2—H2A0.8600O9W—H9WA0.855 (9)
N2—H2B0.8600O9W—H9WB0.852 (9)
C14—N4—C16127.06 (14)O4—C8—C6115.68 (12)
C14—N4—C12109.84 (12)C4—C3—C2120.23 (13)
C16—N4—C12123.07 (13)C4—C3—H3119.9
C11—N5—C10110.75 (12)C2—C3—H3119.9
C11—N5—H5124.6O2—C7—O1125.96 (13)
C10—N5—H5124.6O2—C7—C1117.35 (12)
C2—C1—C6120.02 (12)O1—C7—C1116.65 (12)
C2—C1—C7119.63 (12)N7—C9—C10103.02 (12)
C6—C1—C7120.29 (11)N7—C9—H9A111.2
C4—C5—C6123.75 (12)C10—C9—H9A111.2
C4—C5—N1117.95 (12)N7—C9—H9B111.2
C6—C5—N1118.29 (12)C10—C9—H9B111.2
O5—N1—O6123.96 (15)H9A—C9—H9B109.1
O5—N1—C5118.51 (14)N6—C11—N7127.13 (13)
O6—N1—C5117.52 (13)N6—C11—N5122.26 (13)
C11—N7—C15125.62 (13)N7—C11—N5110.61 (12)
C11—N7—C9109.51 (12)O8—C10—N5125.80 (16)
C15—N7—C9122.51 (13)O8—C10—C9128.18 (15)
C14—N2—H2A120.0N5—C10—C9106.03 (13)
C14—N2—H2B120.0O7—C13—N3126.04 (15)
H2A—N2—H2B120.0O7—C13—C12128.05 (14)
C5—C6—C1117.10 (12)N3—C13—C12105.90 (13)
C5—C6—C8121.54 (12)N7—C15—H15A109.5
C1—C6—C8121.27 (11)N7—C15—H15B109.5
C11—N6—H6A120.0H15A—C15—H15B109.5
C11—N6—H6B120.0N7—C15—H15C109.5
H6A—N6—H6B120.0H15A—C15—H15C109.5
C14—N3—C13110.74 (12)H15B—C15—H15C109.5
C14—N3—H3A124.6N4—C12—C13102.71 (12)
C13—N3—H3A124.6N4—C12—H12A111.2
C3—C2—C1120.78 (13)C13—C12—H12A111.2
C3—C2—H2119.6N4—C12—H12B111.2
C1—C2—H2119.6C13—C12—H12B111.2
N2—C14—N4127.26 (14)H12A—C12—H12B109.1
N2—C14—N3121.98 (13)N4—C16—H16A109.5
N4—C14—N3110.74 (12)N4—C16—H16B109.5
C5—C4—C3118.06 (12)H16A—C16—H16B109.5
C5—C4—H4121.0N4—C16—H16C109.5
C3—C4—H4121.0H16A—C16—H16C109.5
O3—C8—O4126.73 (13)H16B—C16—H16C109.5
O3—C8—C6117.58 (12)H9WA—O9W—H9WB105.1 (14)
C4—C5—N1—O549.1 (2)C1—C6—C8—O4117.14 (14)
C6—C5—N1—O5132.09 (15)C5—C4—C3—C22.1 (2)
C4—C5—N1—O6131.17 (15)C1—C2—C3—C42.6 (2)
C6—C5—N1—O647.61 (19)C2—C1—C7—O255.03 (18)
C4—C5—C6—C11.80 (19)C6—C1—C7—O2127.68 (14)
N1—C5—C6—C1176.91 (12)C2—C1—C7—O1123.06 (15)
C4—C5—C6—C8174.78 (13)C6—C1—C7—O154.23 (18)
N1—C5—C6—C86.51 (19)C11—N7—C9—C102.97 (16)
C2—C1—C6—C51.31 (19)C15—N7—C9—C10166.41 (14)
C7—C1—C6—C5178.58 (12)C15—N7—C11—N614.4 (2)
C2—C1—C6—C8175.28 (12)C9—N7—C11—N6177.21 (14)
C7—C1—C6—C82.00 (18)C15—N7—C11—N5165.78 (14)
C6—C1—C2—C30.8 (2)C9—N7—C11—N52.98 (16)
C7—C1—C2—C3176.46 (13)C10—N5—C11—N6178.51 (13)
C16—N4—C14—N21.0 (3)C10—N5—C11—N71.67 (17)
C12—N4—C14—N2179.12 (15)C11—N5—C10—O8179.93 (16)
C16—N4—C14—N3179.08 (16)C11—N5—C10—C90.30 (17)
C12—N4—C14—N32.76 (17)N7—C9—C10—O8178.31 (17)
C13—N3—C14—N2179.73 (14)N7—C9—C10—N51.93 (16)
C13—N3—C14—N42.03 (16)C14—N3—C13—O7179.98 (16)
C6—C5—C4—C30.1 (2)C14—N3—C13—C120.45 (16)
N1—C5—C4—C3178.63 (13)C14—N4—C12—C132.32 (17)
C5—C6—C8—O3121.68 (14)C16—N4—C12—C13179.43 (15)
C1—C6—C8—O361.89 (17)O7—C13—C12—N4178.47 (16)
C5—C6—C8—O459.29 (17)N3—C13—C12—N41.08 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O9W—H9WA···O20.86 (1)1.94 (2)2.7856 (18)168 (2)
O9W—H9WB···O8i0.85 (1)2.16 (2)2.9241 (18)149 (2)
N2—H2A···O3ii0.862.002.7899 (17)152
N2—H2B···O2iii0.861.952.8000 (17)168
N3—H3A···O1iii0.861.772.6275 (15)177
N5—H5···O4iv0.861.842.6836 (16)166
N6—H6A···O9Wv0.861.962.7952 (17)163
N6—H6B···O3iv0.861.942.7900 (16)171
C4—H4···O5i0.932.593.2071 (19)124
C9—H9B···O6vi0.972.473.212 (2)133
Symmetry codes: (i) x, y, z+1; (ii) x, y+1/2, z1/2; (iii) x, y1/2, z+1/2; (iv) x+1, y1/2, z+1/2; (v) x+1, y+1/2, z1/2; (vi) x+1, y, z+1.
 

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