N,N′-Bis(isonicotino­yl)hydrazine dihydrate at 120 (2) K: a three-dimensional framework built from N—H...O, O—H...O, O—H...N and C—H...O hydrogen bonds

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.

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

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Computing details

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

Crystal data

C12H10N4O2·2H2O	Dx = 1.462 Mg m^−3
Mr = 278.27	Melting point: 540 K
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 833 reflections
a = 28.1492 (15) Å	θ = 4.5–27.5°
b = 24.1628 (13) Å	µ = 0.11 mm^−1
c = 3.7181 (5) Å	T = 120 K
V = 2528.9 (4) Å^3	Block, colourless
Z = 8	0.35 × 0.20 × 0.20 mm
F(000) = 1168

Data collection

Nonius KappaCCD area-detector diffractometer	833 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	675 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
φ and ω scans	θmax = 27.5°, θmin = 4.5°
Absorption correction: multi-scan [SADABS (Sheldrick, 2003) and EvalCCD (Duisenberg et al., 2003)]	h = −36→36
Tmin = 0.937, Tmax = 0.978	k = −30→30
15302 measured reflections	l = −4→4

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.201	H-atom parameters constrained
S = 1.14	w = 1/[σ^2(Fo^2) + (0.1226P)^2 + 7.0985P] where P = (Fo^2 + 2Fc^2)/3
833 reflections	(Δ/σ)max < 0.001
91 parameters	Δρmax = 0.41 e Å^−3
1 restraint	Δρmin = −0.32 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.35707 (13)	0.26019 (16)	0.2482 (12)	0.0257 (9)
C2	0.36390 (15)	0.31526 (16)	0.3314 (13)	0.0306 (10)
C3	0.41024 (13)	0.33563 (17)	0.3426 (14)	0.0319 (10)
N4	0.44886 (12)	0.30459 (14)	0.2753 (12)	0.0343 (9)
C5	0.44154 (13)	0.25193 (18)	0.1957 (15)	0.0340 (10)
C6	0.39693 (14)	0.22780 (17)	0.1814 (14)	0.0315 (10)
C7	0.30916 (14)	0.23363 (16)	0.2290 (14)	0.0281 (9)
O7	0.30409 (10)	0.18720 (11)	0.0982 (10)	0.0337 (8)
N1	0.27270 (10)	0.26211 (13)	0.3668 (11)	0.0279 (8)
O1	0.26980 (10)	0.36509 (11)	0.7349 (10)	0.0327 (8)
H2	0.3376	0.3388	0.3799	0.037*
H3	0.4148	0.3735	0.4009	0.038*
H5	0.4684	0.2294	0.1455	0.041*
H6	0.3936	0.1896	0.1267	0.038*
H1	0.2725	0.2957	0.4580	0.033*
H1A	0.2493	0.3477	0.9229	0.039*
H1B	0.2516	0.3982	0.6516	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0228 (17)	0.0288 (18)	0.0255 (19)	−0.0014 (14)	−0.0002 (17)	0.0026 (18)
C2	0.0261 (19)	0.030 (2)	0.036 (2)	0.0017 (14)	0.0000 (19)	−0.0038 (19)
C3	0.0276 (19)	0.0273 (18)	0.041 (2)	−0.0041 (15)	0.001 (2)	−0.002 (2)
N4	0.0261 (16)	0.0341 (18)	0.043 (2)	−0.0028 (13)	0.0026 (18)	−0.0040 (17)
C5	0.0234 (18)	0.036 (2)	0.043 (3)	−0.0003 (15)	0.004 (2)	−0.008 (2)
C6	0.0245 (19)	0.0288 (18)	0.041 (3)	0.0000 (14)	0.0014 (19)	−0.002 (2)
C7	0.0246 (18)	0.0271 (18)	0.033 (2)	−0.0004 (13)	0.0001 (18)	−0.0018 (18)
O7	0.0276 (14)	0.0287 (15)	0.0449 (18)	−0.0003 (10)	0.0013 (15)	−0.0065 (14)
N1	0.0193 (16)	0.0260 (16)	0.038 (2)	−0.0019 (12)	0.0009 (15)	−0.0038 (16)
O1	0.0282 (14)	0.0269 (14)	0.0429 (18)	0.0017 (10)	0.0017 (14)	−0.0001 (15)

Geometric parameters (Å, º)

C1—C2	1.380 (6)	C5—H5	0.95
C1—C6	1.390 (5)	C6—H6	0.95
C1—C7	1.495 (5)	C7—O7	1.231 (5)
C2—C3	1.395 (5)	C7—N1	1.338 (5)
C2—H2	0.95	N1—N1^i	1.405 (6)
C3—N4	1.344 (5)	N1—H1	0.88
C3—H3	0.95	O1—H1A	1.00
N4—C5	1.322 (6)	O1—H1B	1.00
C5—C6	1.386 (5)
C2—C1—C6	118.1 (4)	C6—C5—H5	118.2
C2—C1—C7	123.4 (3)	C5—C6—C1	119.2 (4)
C6—C1—C7	118.5 (3)	C5—C6—H6	120.4
C1—C2—C3	118.5 (4)	C1—C6—H6	120.4
C1—C2—H2	120.7	O7—C7—N1	122.1 (4)
C3—C2—H2	120.7	O7—C7—C1	121.0 (3)
N4—C3—C2	123.6 (4)	N1—C7—C1	116.9 (3)
N4—C3—H3	118.2	C7—N1—N1^i	118.9 (3)
C2—C3—H3	118.2	C7—N1—H1	128.9
C5—N4—C3	116.9 (3)	N1^i—N1—H1	112.2
N4—C5—C6	123.7 (4)	H1A—O1—H1B	104.9
N4—C5—H5	118.2
C6—C1—C2—C3	0.3 (7)	C2—C1—C7—O7	168.1 (5)
C7—C1—C2—C3	179.8 (5)	C6—C1—C7—O7	−12.4 (7)
C1—C2—C3—N4	0.3 (8)	C7—N1—N1^i—C7^i	−128.1 (5)
C2—C3—N4—C5	−0.2 (8)	C1—C7—N1—N1^i	−177.7 (3)
C3—N4—C5—C6	−0.5 (8)	C2—C1—C7—N1	−13.3 (7)
N4—C5—C6—C1	1.0 (8)	C6—C1—C7—N1	166.2 (5)
C2—C1—C6—C5	−0.9 (7)	O7—C7—N1—N1^i	0.9 (6)
C7—C1—C6—C5	179.5 (5)

Symmetry code: (i) −x+1/2, −y+1/2, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.88	1.97	2.841 (4)	171
O1—H1A···O7^ii	1.00	1.84	2.783 (4)	156
O1—H1B···N4^iii	1.00	1.93	2.892 (5)	161
C2—H2···O1	0.95	2.41	3.274 (5)	152
C3—H3···O7^iv	0.95	2.43	3.250 (5)	145

Symmetry codes: (ii) −x+1/2, −y+1/2, z+1; (iii) x−1/4, −y+3/4, z+1/4; (iv) −x+3/4, y+1/4, z+3/4.