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In the title compound, C12H10N4O2·2H2O, the hydrazine component lies across a twofold rotation axis. The mol­ecular components are linked into a complex three-dimensional framework by a combination of N—H...O, O—H...O, O—H...N and C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807010112/gg3079sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807010112/gg3079Isup2.hkl
Contains datablock I

CCDC reference: 642991

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.066
  • wR factor = 0.201
  • Data-to-parameter ratio = 9.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.53 From the CIF: _reflns_number_total 833 Count of symmetry unique reflns 839 Completeness (_total/calc) 99.28% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: Authors Portilla and Quiroga prepared and crystallised the compound; authors de la Torre and Cobo collected the diffraction data; author Low solved and refined the structure; authors Glidewell & Cobo analysed the structure and wrote the paper.


1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999) and WinGX (Farrugia, 1999); program(s) used to refine structure: OSCAIL (McArdle, 2003) and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

N,N'-Bis(isonicotinoyl)hydrazine dihydrate top
Crystal data top
C12H10N4O2·2H2ODx = 1.462 Mg m3
Mr = 278.27Melting point: 540 K
Orthorhombic, Fdd2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2dCell parameters from 833 reflections
a = 28.1492 (15) Åθ = 4.5–27.5°
b = 24.1628 (13) ŵ = 0.11 mm1
c = 3.7181 (5) ÅT = 120 K
V = 2528.9 (4) Å3Block, colourless
Z = 80.35 × 0.20 × 0.20 mm
F(000) = 1168
Data collection top
Nonius KappaCCD area-detector
diffractometer
833 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode675 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
φ and ω scansθmax = 27.5°, θmin = 4.5°
Absorption correction: multi-scan
[SADABS (Sheldrick, 2003) and EvalCCD (Duisenberg et al., 2003)]
h = 3636
Tmin = 0.937, Tmax = 0.978k = 3030
15302 measured reflectionsl = 44
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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.201H-atom parameters constrained
S = 1.14 w = 1/[σ2(Fo2) + (0.1226P)2 + 7.0985P]
where P = (Fo2 + 2Fc2)/3
833 reflections(Δ/σ)max < 0.001
91 parametersΔρmax = 0.41 e Å3
1 restraintΔρmin = 0.32 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.35707 (13)0.26019 (16)0.2482 (12)0.0257 (9)
C20.36390 (15)0.31526 (16)0.3314 (13)0.0306 (10)
C30.41024 (13)0.33563 (17)0.3426 (14)0.0319 (10)
N40.44886 (12)0.30459 (14)0.2753 (12)0.0343 (9)
C50.44154 (13)0.25193 (18)0.1957 (15)0.0340 (10)
C60.39693 (14)0.22780 (17)0.1814 (14)0.0315 (10)
C70.30916 (14)0.23363 (16)0.2290 (14)0.0281 (9)
O70.30409 (10)0.18720 (11)0.0982 (10)0.0337 (8)
N10.27270 (10)0.26211 (13)0.3668 (11)0.0279 (8)
O10.26980 (10)0.36509 (11)0.7349 (10)0.0327 (8)
H20.33760.33880.37990.037*
H30.41480.37350.40090.038*
H50.46840.22940.14550.041*
H60.39360.18960.12670.038*
H10.27250.29570.45800.033*
H1A0.24930.34770.92290.039*
H1B0.25160.39820.65160.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0228 (17)0.0288 (18)0.0255 (19)0.0014 (14)0.0002 (17)0.0026 (18)
C20.0261 (19)0.030 (2)0.036 (2)0.0017 (14)0.0000 (19)0.0038 (19)
C30.0276 (19)0.0273 (18)0.041 (2)0.0041 (15)0.001 (2)0.002 (2)
N40.0261 (16)0.0341 (18)0.043 (2)0.0028 (13)0.0026 (18)0.0040 (17)
C50.0234 (18)0.036 (2)0.043 (3)0.0003 (15)0.004 (2)0.008 (2)
C60.0245 (19)0.0288 (18)0.041 (3)0.0000 (14)0.0014 (19)0.002 (2)
C70.0246 (18)0.0271 (18)0.033 (2)0.0004 (13)0.0001 (18)0.0018 (18)
O70.0276 (14)0.0287 (15)0.0449 (18)0.0003 (10)0.0013 (15)0.0065 (14)
N10.0193 (16)0.0260 (16)0.038 (2)0.0019 (12)0.0009 (15)0.0038 (16)
O10.0282 (14)0.0269 (14)0.0429 (18)0.0017 (10)0.0017 (14)0.0001 (15)
Geometric parameters (Å, º) top
C1—C21.380 (6)C5—H50.95
C1—C61.390 (5)C6—H60.95
C1—C71.495 (5)C7—O71.231 (5)
C2—C31.395 (5)C7—N11.338 (5)
C2—H20.95N1—N1i1.405 (6)
C3—N41.344 (5)N1—H10.88
C3—H30.95O1—H1A1.00
N4—C51.322 (6)O1—H1B1.00
C5—C61.386 (5)
C2—C1—C6118.1 (4)C6—C5—H5118.2
C2—C1—C7123.4 (3)C5—C6—C1119.2 (4)
C6—C1—C7118.5 (3)C5—C6—H6120.4
C1—C2—C3118.5 (4)C1—C6—H6120.4
C1—C2—H2120.7O7—C7—N1122.1 (4)
C3—C2—H2120.7O7—C7—C1121.0 (3)
N4—C3—C2123.6 (4)N1—C7—C1116.9 (3)
N4—C3—H3118.2C7—N1—N1i118.9 (3)
C2—C3—H3118.2C7—N1—H1128.9
C5—N4—C3116.9 (3)N1i—N1—H1112.2
N4—C5—C6123.7 (4)H1A—O1—H1B104.9
N4—C5—H5118.2
C6—C1—C2—C30.3 (7)C2—C1—C7—O7168.1 (5)
C7—C1—C2—C3179.8 (5)C6—C1—C7—O712.4 (7)
C1—C2—C3—N40.3 (8)C7—N1—N1i—C7i128.1 (5)
C2—C3—N4—C50.2 (8)C1—C7—N1—N1i177.7 (3)
C3—N4—C5—C60.5 (8)C2—C1—C7—N113.3 (7)
N4—C5—C6—C11.0 (8)C6—C1—C7—N1166.2 (5)
C2—C1—C6—C50.9 (7)O7—C7—N1—N1i0.9 (6)
C7—C1—C6—C5179.5 (5)
Symmetry code: (i) x+1/2, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.881.972.841 (4)171
O1—H1A···O7ii1.001.842.783 (4)156
O1—H1B···N4iii1.001.932.892 (5)161
C2—H2···O10.952.413.274 (5)152
C3—H3···O7iv0.952.433.250 (5)145
Symmetry codes: (ii) x+1/2, y+1/2, z+1; (iii) x1/4, y+3/4, z+1/4; (iv) x+3/4, y+1/4, z+3/4.
 

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