Disodium 3-oxobutane-2,2-diylbis(diazeniumdiolate) dihydrate

Arulsamy, N.; Bohle, D.S.

doi:10.1107/S1600536805009803

Disodium 3-oxobutane-2,2-diylbis(diazeniumdiolate) dihydrate

The two diazeniumdiolate substitutents in the anion of the title compound, 2Na⁺·C₄H₆N₄O₅^2-·2H₂O, adopt a Z configuration and are chelated to the Na⁺ cations. The water molecules are also coordinated to the cations.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805009803/om6232sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805009803/om6232Isup2.hkl Contains datablock I

CCDC reference: 272061

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R factor = 0.043
wR factor = 0.117
Data-to-parameter ratio = 10.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.76 mm
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C1
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.61 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XSCANS (Bruker, Year?); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Disodium 3-oxobutane-2,2-diylbis(diazeniumdiolate) dihydrate top

Crystal data top

2Na⁺·C₄H₆N₄O₅²⁻·2H₂O	Z = 2
M_r = 272.14	F(000) = 280
Triclinic, P1	D_x = 1.692 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.625 (1) Å	Cell parameters from 27 reflections
b = 8.525 (1) Å	θ = 4.8–12.5°
c = 9.821 (2) Å	µ = 0.22 mm⁻¹
α = 92.62 (1)°	T = 298 K
β = 103.42 (1)°	Chunk, colorless
γ = 96.89 (1)°	0.76 × 0.52 × 0.44 mm
V = 534.07 (15) Å³

Data collection top

Bruker P4 diffractometer	R_int = 0.011
Radiation source: fine-focus sealed tube	θ_max = 25.0°, θ_min = 2.1°
Graphite monochromator	h = −7→1
ω scans	k = −10→10
2371 measured reflections	l = −11→11
1854 independent reflections	3 standard reflections every 97 reflections
1751 reflections with I > 2σ(I)	intensity decay: 1%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0571P)² + 0.5532P] where P = (F_o² + 2F_c²)/3
1854 reflections	(Δ/σ)_max = 0.003
170 parameters	Δρ_max = 0.66 e Å⁻³
0 restraints	Δρ_min = −0.56 e Å⁻³

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

	x	y	z	U_iso*/U_eq
Na1	0.07100 (16)	−0.16434 (11)	0.87931 (11)	0.0384 (3)
Na2	0.28453 (14)	0.52215 (11)	1.09131 (10)	0.0334 (3)
C1	0.4168 (6)	0.2147 (4)	0.4625 (3)	0.0605 (9)
H1A	0.5478	0.2490	0.4400	0.091*
H1B	0.3036	0.2331	0.3867	0.091*
H1C	0.4069	0.1036	0.4766	0.091*
C2	0.4048 (4)	0.3053 (3)	0.5936 (3)	0.0355 (6)
O2C	0.5380 (3)	0.4121 (2)	0.6510 (2)	0.0484 (5)
C3	0.2051 (3)	0.2673 (2)	0.6479 (2)	0.0249 (5)
N1	0.1975 (3)	0.1101 (2)	0.70473 (18)	0.0228 (4)
O1	0.0239 (2)	0.04829 (18)	0.73319 (18)	0.0306 (4)
N2	0.3711 (3)	0.0503 (2)	0.7332 (2)	0.0287 (4)
O2	0.3599 (3)	−0.08151 (19)	0.79023 (19)	0.0361 (4)
N3	0.2110 (3)	0.3804 (2)	0.76766 (18)	0.0231 (4)
O3	0.3506 (2)	0.37198 (19)	0.88527 (15)	0.0299 (4)
N4	0.0706 (3)	0.4745 (2)	0.7505 (2)	0.0298 (4)
O4	0.0762 (3)	0.56230 (19)	0.86220 (17)	0.0362 (4)
C4	0.0132 (4)	0.2700 (3)	0.5280 (3)	0.0409 (6)
H4A	−0.0024	0.1790	0.4633	0.061*
H4B	0.0301	0.3647	0.4803	0.061*
H4C	−0.1092	0.2679	0.5649	0.061*
O1W	0.2078 (3)	−0.2060 (2)	1.1189 (2)	0.0375 (4)
H1	0.133 (6)	−0.167 (4)	1.162 (4)	0.058 (10)*
H2	0.321 (6)	−0.157 (4)	1.155 (4)	0.056 (10)*
O2W	−0.2700 (4)	−0.1986 (4)	0.9056 (3)	0.0699 (8)
H3	−0.287 (6)	−0.212 (4)	0.990 (4)	0.064 (11)*
H4	−0.356 (9)	−0.154 (6)	0.874 (6)	0.107 (18)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Na1	0.0400 (6)	0.0338 (5)	0.0504 (6)	0.0122 (4)	0.0225 (5)	0.0168 (4)
Na2	0.0320 (5)	0.0341 (5)	0.0344 (5)	0.0055 (4)	0.0087 (4)	−0.0023 (4)
C1	0.070 (2)	0.063 (2)	0.0520 (18)	−0.0056 (16)	0.0316 (16)	−0.0109 (15)
C2	0.0413 (14)	0.0315 (12)	0.0327 (12)	0.0012 (11)	0.0086 (10)	0.0039 (10)
O2C	0.0502 (11)	0.0493 (11)	0.0436 (11)	−0.0062 (9)	0.0138 (9)	0.0004 (9)
C3	0.0335 (11)	0.0197 (10)	0.0205 (10)	0.0042 (8)	0.0046 (9)	−0.0004 (8)
N1	0.0230 (9)	0.0197 (8)	0.0257 (9)	0.0021 (7)	0.0066 (7)	−0.0009 (7)
O1	0.0228 (8)	0.0264 (8)	0.0451 (9)	0.0037 (6)	0.0128 (7)	0.0046 (7)
N2	0.0252 (10)	0.0260 (9)	0.0366 (10)	0.0070 (7)	0.0086 (8)	0.0048 (8)
O2	0.0319 (9)	0.0321 (9)	0.0489 (10)	0.0135 (7)	0.0126 (8)	0.0146 (8)
N3	0.0272 (9)	0.0203 (8)	0.0207 (9)	0.0044 (7)	0.0028 (7)	0.0011 (7)
O3	0.0315 (8)	0.0351 (9)	0.0199 (8)	0.0068 (7)	−0.0006 (6)	−0.0014 (6)
N4	0.0363 (11)	0.0249 (9)	0.0298 (10)	0.0089 (8)	0.0087 (8)	0.0017 (8)
O4	0.0483 (10)	0.0288 (8)	0.0348 (9)	0.0118 (7)	0.0146 (8)	−0.0038 (7)
C4	0.0504 (15)	0.0367 (13)	0.0290 (12)	0.0110 (11)	−0.0054 (11)	−0.0018 (10)
O1W	0.0288 (9)	0.0365 (10)	0.0460 (11)	0.0030 (8)	0.0097 (8)	−0.0099 (8)
O2W	0.0448 (13)	0.115 (2)	0.0723 (17)	0.0435 (14)	0.0324 (12)	0.0616 (16)

Geometric parameters (Å, º) top

Na1—O2W	2.318 (2)	C2—C3	1.543 (3)
Na1—O2	2.3317 (19)	O2C—Na2ⁱⁱⁱ	2.536 (2)
Na1—O4ⁱ	2.3336 (19)	C3—N1	1.475 (3)
Na1—O1	2.3682 (18)	C3—N3	1.476 (3)
Na1—O1W	2.377 (2)	C3—C4	1.523 (3)
Na1—Na2ⁱ	3.6781 (14)	N1—N2	1.290 (3)
Na1—Na2ⁱⁱ	3.6889 (14)	N1—O1	1.303 (2)
Na1—Na1ⁱⁱ	3.926 (2)	N2—O2	1.280 (2)
Na2—O4	2.414 (2)	N3—N4	1.287 (3)
Na2—O3ⁱⁱⁱ	2.4311 (19)	N3—O3	1.312 (2)
Na2—O1W^iv	2.448 (2)	O3—Na2ⁱⁱⁱ	2.4311 (19)
Na2—O3	2.4968 (18)	N4—O4	1.290 (2)
Na2—O2Cⁱⁱⁱ	2.536 (2)	O4—Na1^iv	2.3336 (19)
Na2—O4^v	2.561 (2)	O4—Na2^v	2.561 (2)
Na2—O2Wⁱⁱ	2.750 (3)	C4—H4A	0.9600
Na2—Na1^iv	3.6781 (14)	C4—H4B	0.9600
Na2—Na1ⁱⁱ	3.6889 (14)	C4—H4C	0.9600
Na2—Na2^v	3.7457 (19)	O1W—Na2ⁱ	2.448 (2)
Na2—Na2ⁱⁱⁱ	3.7528 (19)	O1W—H1	0.81 (4)
C1—C2	1.494 (4)	O1W—H2	0.80 (4)
C1—H1A	0.9600	O2W—Na2ⁱⁱ	2.750 (3)
C1—H1B	0.9600	O2W—H3	0.87 (4)
C1—H1C	0.9600	O2W—H4	0.74 (6)
C2—O2C	1.206 (3)

O2W—Na1—O2	160.36 (9)	O2Cⁱⁱⁱ—Na2—Na2^v	129.81 (6)
O2W—Na1—O4ⁱ	91.43 (9)	O4^v—Na2—Na2^v	39.70 (4)
O2—Na1—O4ⁱ	99.60 (7)	O2Wⁱⁱ—Na2—Na2^v	90.78 (6)
O2W—Na1—O1	95.10 (8)	Na1^iv—Na2—Na2^v	59.58 (3)
O2—Na1—O1	66.06 (6)	Na1ⁱⁱ—Na2—Na2^v	59.30 (3)
O4ⁱ—Na1—O1	139.92 (8)	O4—Na2—Na2ⁱⁱⁱ	85.63 (6)
O2W—Na1—O1W	91.92 (9)	O3ⁱⁱⁱ—Na2—Na2ⁱⁱⁱ	41.05 (4)
O2—Na1—O1W	105.93 (8)	O1W^iv—Na2—Na2ⁱⁱⁱ	114.61 (7)
O4ⁱ—Na1—O1W	79.80 (7)	O3—Na2—Na2ⁱⁱⁱ	39.75 (4)
O1—Na1—O1W	139.18 (8)	O2Cⁱⁱⁱ—Na2—Na2ⁱⁱⁱ	106.05 (6)
O2W—Na1—Na2ⁱ	100.03 (7)	O4^v—Na2—Na2ⁱⁱⁱ	153.19 (6)
O2—Na1—Na2ⁱ	98.85 (5)	O2Wⁱⁱ—Na2—Na2ⁱⁱⁱ	82.39 (6)
O4ⁱ—Na1—Na2ⁱ	40.02 (5)	Na1^iv—Na2—Na2ⁱⁱⁱ	95.48 (4)
O1—Na1—Na2ⁱ	164.86 (5)	Na1ⁱⁱ—Na2—Na2ⁱⁱⁱ	118.33 (4)
O1W—Na1—Na2ⁱ	41.06 (5)	Na2^v—Na2—Na2ⁱⁱⁱ	124.14 (5)
O2W—Na1—Na2ⁱⁱ	48.12 (8)	C2—C1—H1A	109.5
O2—Na1—Na2ⁱⁱ	141.73 (6)	C2—C1—H1B	109.5
O4ⁱ—Na1—Na2ⁱⁱ	43.48 (5)	H1A—C1—H1B	109.5
O1—Na1—Na2ⁱⁱ	131.58 (6)	C2—C1—H1C	109.5
O1W—Na1—Na2ⁱⁱ	80.70 (6)	H1A—C1—H1C	109.5
Na2ⁱ—Na1—Na2ⁱⁱ	61.12 (3)	H1B—C1—H1C	109.5
O2W—Na1—Na1ⁱⁱ	64.33 (9)	O2C—C2—C1	122.1 (3)
O2—Na1—Na1ⁱⁱ	113.62 (6)	O2C—C2—C3	120.1 (2)
O4ⁱ—Na1—Na1ⁱⁱ	139.97 (6)	C1—C2—C3	117.6 (2)
O1—Na1—Na1ⁱⁱ	76.78 (5)	C2—O2C—Na2ⁱⁱⁱ	130.70 (17)
O1W—Na1—Na1ⁱⁱ	70.34 (6)	N1—C3—N3	105.18 (16)
Na2ⁱ—Na1—Na1ⁱⁱ	110.09 (4)	N1—C3—C4	109.51 (18)
Na2ⁱⁱ—Na1—Na1ⁱⁱ	104.17 (4)	N3—C3—C4	112.41 (18)
O4—Na2—O3ⁱⁱⁱ	110.66 (7)	N1—C3—C2	110.63 (18)
O4—Na2—O1W^iv	76.85 (7)	N3—C3—C2	109.71 (18)
O3ⁱⁱⁱ—Na2—O1W^iv	88.57 (7)	C4—C3—C2	109.34 (19)
O4—Na2—O3	62.74 (6)	N2—N1—O1	124.89 (17)
O3ⁱⁱⁱ—Na2—O3	80.81 (6)	N2—N1—C3	116.45 (17)
O1W^iv—Na2—O3	130.56 (7)	O1—N1—C3	118.40 (17)
O4—Na2—O2Cⁱⁱⁱ	157.05 (7)	N1—O1—Na1	112.62 (12)
O3ⁱⁱⁱ—Na2—O2Cⁱⁱⁱ	70.61 (6)	O2—N2—N1	114.19 (17)
O1W^iv—Na2—O2Cⁱⁱⁱ	80.30 (7)	N2—O2—Na1	119.91 (13)
O3—Na2—O2Cⁱⁱⁱ	137.63 (7)	N4—N3—O3	124.93 (17)
O4—Na2—O4^v	82.37 (7)	N4—N3—C3	117.00 (17)
O3ⁱⁱⁱ—Na2—O4^v	164.26 (7)	O3—N3—C3	117.97 (16)
O1W^iv—Na2—O4^v	85.84 (7)	N3—O3—Na2ⁱⁱⁱ	120.39 (13)
O3—Na2—O4^v	113.85 (6)	N3—O3—Na2	113.70 (12)
O2Cⁱⁱⁱ—Na2—O4^v	93.92 (7)	Na2ⁱⁱⁱ—O3—Na2	99.19 (6)
O4—Na2—O2Wⁱⁱ	104.45 (8)	N3—N4—O4	113.62 (18)
O3ⁱⁱⁱ—Na2—O2Wⁱⁱ	106.42 (7)	N4—O4—Na1^iv	126.84 (14)
O1W^iv—Na2—O2Wⁱⁱ	162.94 (8)	N4—O4—Na2	123.29 (13)
O3—Na2—O2Wⁱⁱ	61.69 (7)	Na1^iv—O4—Na2	101.54 (7)
O2Cⁱⁱⁱ—Na2—O2Wⁱⁱ	96.76 (8)	N4—O4—Na2^v	102.52 (13)
O4^v—Na2—O2Wⁱⁱ	77.57 (6)	Na1^iv—O4—Na2^v	97.70 (7)
O4—Na2—Na1^iv	38.44 (4)	Na2—O4—Na2^v	97.63 (7)
O3ⁱⁱⁱ—Na2—Na1^iv	95.18 (5)	C3—C4—H4A	109.5
O1W^iv—Na2—Na1^iv	39.62 (5)	C3—C4—H4B	109.5
O3—Na2—Na1^iv	93.20 (5)	H4A—C4—H4B	109.5
O2Cⁱⁱⁱ—Na2—Na1^iv	119.35 (6)	C3—C4—H4C	109.5
O4^v—Na2—Na1^iv	89.88 (5)	H4A—C4—H4C	109.5
O2Wⁱⁱ—Na2—Na1^iv	142.63 (7)	H4B—C4—H4C	109.5
O4—Na2—Na1ⁱⁱ	91.97 (5)	Na1—O1W—Na2ⁱ	99.32 (7)
O3ⁱⁱⁱ—Na2—Na1ⁱⁱ	144.02 (5)	Na1—O1W—H1	106 (2)
O1W^iv—Na2—Na1ⁱⁱ	124.66 (6)	Na2ⁱ—O1W—H1	132 (3)
O3—Na2—Na1ⁱⁱ	85.72 (5)	Na1—O1W—H2	116 (3)
O2Cⁱⁱⁱ—Na2—Na1ⁱⁱ	99.29 (6)	Na2ⁱ—O1W—H2	103 (3)
O4^v—Na2—Na1ⁱⁱ	38.82 (4)	H1—O1W—H2	102 (3)
O2Wⁱⁱ—Na2—Na1ⁱⁱ	38.87 (5)	Na1—O2W—Na2ⁱⁱ	93.01 (9)
Na1^iv—Na2—Na1ⁱⁱ	118.88 (3)	Na1—O2W—H3	117 (2)
O4—Na2—Na2^v	42.67 (5)	Na2ⁱⁱ—O2W—H3	79 (2)
O3ⁱⁱⁱ—Na2—Na2^v	152.31 (6)	Na1—O2W—H4	128 (4)
O1W^iv—Na2—Na2^v	78.68 (6)	Na2ⁱⁱ—O2W—H4	127 (4)
O3—Na2—Na2^v	88.93 (5)	H3—O2W—H4	104 (5)

O1—N1—N2—O2	1.9 (3)	O3—N3—N4—O4	−0.7 (3)

Symmetry codes: (i) x, y−1, z; (ii) −x, −y, −z+2; (iii) −x+1, −y+1, −z+2; (iv) x, y+1, z; (v) −x, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1···O1ⁱⁱ	0.81 (4)	1.96 (4)	2.761 (3)	173 (3)
O2W—H3···O3ⁱⁱ	0.87 (4)	1.94 (4)	2.699 (3)	144 (3)
O2W—H4···O2^vi	0.74 (6)	2.05 (6)	2.774 (3)	166 (6)

Symmetry codes: (ii) −x, −y, −z+2; (vi) x−1, y, z.

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page