5,7,9,10-Tetra­hydro-5β,10β-methano-3aα,8aα-methyl­propenocyclo­octa­[1,2-c:5,6-c′]dipyrazole-3,8(2H,4H)-dione monohydrate

Djaidi, D.; Bishop, R.; Craig, D.C.; Scudder, M.L.

doi:10.1107/S1600536808013512

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1055

doi:10.1107/S1600536808013512

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5,7,9,10-Tetrahydro-5β,10β-methano-3aα,8aα-methylpropenocycloocta[1,2-c:5,6-c′]dipyrazole-3,8(2H,4H)-dione monohydrate

Djamal Djaidi,^a Roger Bishop,^a Donald C. Craig ^a and Marcia L. Scudder ^a ^*

^aSchool of Chemistry, University of New South Wales, Sydney, Australia 2052
^*Correspondence e-mail: m.scudder@unsw.edu.au

(Received 5 May 2008; accepted 7 May 2008; online 10 May 2008)

The racemic title compound, C₁₅H₁₆N₄O₂·H₂O, crystallizes as a hydrogen-bonded layer structure incorporating the solvent water molecules. Within the layers, there are three distinct hydrogen-bonding motifs which can be classified as R₂²(8), R₄²(8) and R₄⁴(12).

Related literature

For related literature, see: Chan et al. (2008 ); Yue et al. (1997 , 2000 , 2007 ). For hydrogen-bonding analysis, see: Etter (1990 ).

Experimental

Crystal data

C₁₅H₁₆N₄O₂·H₂O
M_r = 302.3
Triclinic, $[P \overline 1]$
a = 6.478 (1) Å
b = 8.157 (1) Å
c = 14.812 (2) Å
α = 85.412 (9)°
β = 88.369 (8)°
γ = 67.089 (11)°
V = 718.6 (2) Å³
Z = 2
Cu Kα radiation
μ = 0.82 mm⁻¹
T = 294 K
0.30 × 0.25 × 0.22 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
2695 measured reflections
2695 independent reflections
2365 reflections with I > 2σ(I)
1 standard reflections frequency: 30 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.089
S = 1.64
2357 reflections
200 parameters
H-atom parameters not refined
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—HN2⋯OWⁱ	1.00	1.83	2.763 (3)	154
N4—HN4⋯O2ⁱⁱ	1.00	2.00	2.858 (2)	143
OW—H1OW⋯O1	1.00	1.85	2.844 (2)	169
OW—H2OW⋯O1ⁱⁱⁱ	1.00	1.81	2.796 (2)	169
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x+1, -y, -z; (iii) -x, -y+2, -z+1.

Data collection: CAD-4 (Schagen et al., 1989 ); cell refinement: CAD-4; data reduction: local program; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: RAELS (Rae, 2000 ); molecular graphics: ORTEPII (Johnson, 1976 ) and CrystalMaker (CrystalMaker Software, 2005 ); software used to prepare material for publication: local programs.

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536808013512/tk2269sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808013512/tk2269Isup2.hkl

checkCIF report

Comment top

The structural core of the title compound (I) is the rare tricyclo[5.3.1.1^3,9]dodecane ring system, the chemistry of which has been described by us earlier (Yue et al. 1997, 2000, 2007; Chan et al. 2008). Compound (I), Fig. 1, forms hydrogen bonded layers that lie in the (1 - 2 1) plane, Fig. 2 & Table 1. There are three motifs, all of which are centrosymmetric, which repeat within the layer. The first of these incorporates pairs of N—H···O=C hydrogen bonds. The second and third alternate along a, one comprising cycles of O—H···O=C hydrogen bonds and involving the lattice water molecules, and the other including N—H···O (water) interactions as well. In Etter's notation, the three cycles can be described as R₂²(8), R₄²(8) and R₄⁴(12), respectively (Etter, 1990).

Related literature top

For related literature, see: Chan et al. (2008); Yue et al. (1997, 2000, 2007). For hydrogen-bonding analysis, see: Etter (1990).

Experimental top

Racemic 3,7-bis(methoxycarbonyl)-5-methylidenetricyclo[5.3.1.1^3,9]dodecane-2,8-dione (Yue et al., 1997) (1.00 g, 3.24 mmol) was ground into a fine powder and then a small volume of hydrazine hydrate added. After stirring the mixture for 30 min, the resulting solid was filtered, washed with a small amount of diethyl ether and dried. The creamy material was recrystallized from methanol to give shiny crystals of the dipyrazole product (0.60 g, 68%), m.p. 335–343°C (decomp.). Found: C 61.90, H 6.24, N 20.97; C₁₅H₁₆N₄O₂.H₂O requires C 61.75, H 5.93, N 20.58%. X-ray quality crystals were obtained from a methanol solution of (I).

Computing details top

Data collection: CAD-4 (Schagen et al., 1989); cell refinement: CAD-4 (Schagen et al., 1989); data reduction: Local program; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: RAELS (Rae, 2000); molecular graphics: ORTEPII (Johnson, 1976) and CrystalMaker (CrystalMaker Software, 2005); software used to prepare material for publication: Local programs.

Figures top

	Fig. 1. Molecular structure of (I) showing atom numbering scheme and dispacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Part of one hydrogen bonded layer in the crystal structure of (I) showing the three hydrogen bonded packing motifs. Enantiomers are distinguished by C shading and hydrogen bonds are shown as dashed bonds.

(I) top

Crystal data top

C₁₅H₁₆N₄O₂·H₂O	Z = 2
M_r = 302.3	F(000) = 320.0
Triclinic, P1	D_x = 1.40 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 6.478 (1) Å	Cell parameters from 10 reflections
b = 8.157 (1) Å	θ = 20–25°
c = 14.812 (2) Å	µ = 0.82 mm⁻¹
α = 85.412 (9)°	T = 294 K
β = 88.369 (8)°	Irregular, colourless
γ = 67.089 (11)°	0.30 × 0.25 × 0.22 mm
V = 718.6 (2) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	h = −7→7
ω–2θ scans	k = −9→9
2695 measured reflections	l = 0→18
2695 independent reflections	1 standard reflections every 30 min
2365 reflections with I > 2σ(I)	intensity decay: none
θ_max = 70°

Refinement top

Refinement on F	0 restraints
R[F² > 2σ(F²)] = 0.045	H-atom parameters not refined
wR(F²) = 0.089	w = 1/[σ²(F) + 0.0004F²]
S = 1.64	(Δ/σ)_max = 0.003
2357 reflections	Δρ_max = 0.34 e Å⁻³
200 parameters	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₅H₁₆N₄O₂·H₂O	γ = 67.089 (11)°
M_r = 302.3	V = 718.6 (2) Å³
Triclinic, P1	Z = 2
a = 6.478 (1) Å	Cu Kα radiation
b = 8.157 (1) Å	µ = 0.82 mm⁻¹
c = 14.812 (2) Å	T = 294 K
α = 85.412 (9)°	0.30 × 0.25 × 0.22 mm
β = 88.369 (8)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2365 reflections with I > 2σ(I)
2695 measured reflections	1 standard reflections every 30 min
2695 independent reflections	intensity decay: none

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.089	H-atom parameters not refined
S = 1.64	Δρ_max = 0.34 e Å⁻³
2357 reflections	Δρ_min = −0.22 e Å⁻³
200 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.2515 (2)	0.7918 (2)	0.4385 (1)	0.0547 (4)
O2	0.5206 (3)	0.2155 (2)	−0.00820 (9)	0.0554 (5)
N1	0.7574 (3)	0.6073 (2)	0.3265 (1)	0.0467 (4)
N2	0.6047 (3)	0.7257 (2)	0.3836 (1)	0.0444 (4)
N3	0.3972 (3)	0.0850 (2)	0.2088 (1)	0.0454 (4)
N4	0.4023 (3)	0.0817 (2)	0.1133 (1)	0.0450 (4)
C1	0.7515 (3)	0.2116 (3)	0.3103 (1)	0.0473 (5)
C2	0.7756 (3)	0.3578 (3)	0.2444 (1)	0.0423 (5)
C3	0.6519 (3)	0.5264 (2)	0.2887 (1)	0.0357 (4)
C4	0.4109 (3)	0.5822 (2)	0.3178 (1)	0.0327 (4)
C5	0.3650 (3)	0.4204 (2)	0.3612 (1)	0.0389 (4)
C6	0.5016 (3)	0.2421 (2)	0.3198 (1)	0.0398 (4)
C7	0.4370 (3)	0.2210 (2)	0.2270 (1)	0.0355 (4)
C8	0.4732 (3)	0.3268 (2)	0.1447 (1)	0.0344 (4)
C9	0.6971 (3)	0.3513 (3)	0.1481 (1)	0.0420 (5)
C10	0.2364 (3)	0.7009 (2)	0.2481 (1)	0.0407 (5)
C11	0.1748 (3)	0.6505 (2)	0.1653 (1)	0.0399 (4)
C12	0.2665 (3)	0.4969 (2)	0.1200 (1)	0.0414 (5)
C13	−0.0245 (4)	0.7972 (3)	0.1192 (2)	0.0680 (7)
C14	0.4063 (3)	0.7116 (2)	0.3883 (1)	0.0379 (4)
C15	0.4741 (3)	0.2025 (2)	0.0724 (1)	0.0386 (4)
OW	0.1914 (3)	1.1247 (2)	0.5054 (1)	0.0586 (5)
HN2	0.6410	0.8123	0.4175	0.044
HN4	0.3574	−0.0013	0.0801	0.045
H1C1	0.8130	0.2158	0.3709	0.047
H2C1	0.8364	0.0923	0.2867	0.047
HC2	0.9377	0.3389	0.2415	0.042
H1C5	0.2021	0.4462	0.3535	0.039
H2C5	0.4019	0.4063	0.4272	0.039
HC6	0.4903	0.1431	0.3614	0.040
H1C9	0.6792	0.4657	0.1126	0.042
H2C9	0.8150	0.2493	0.1194	0.042
H1C10	0.2861	0.8001	0.2289	0.041
H2C10	0.0935	0.7491	0.2830	0.041
HC12	0.1872	0.4965	0.0631	0.041
H1C13	−0.0602	0.7554	0.0622	0.068
H2C13	−0.1567	0.8285	0.1606	0.068
H3C13	0.0115	0.9048	0.1042	0.068
H1OW	0.2311	1.0064	0.4799	0.059
H2OW	0.0335	1.1680	0.5279	0.059

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0468 (8)	0.0597 (9)	0.0644 (9)	−0.0226 (7)	0.0129 (7)	−0.0380 (7)
O2	0.086 (1)	0.0521 (8)	0.0354 (7)	−0.0325 (8)	0.0048 (7)	−0.0159 (6)
N1	0.0379 (8)	0.057 (1)	0.052 (1)	−0.0223 (7)	0.0050 (7)	−0.0231 (8)
N2	0.0428 (9)	0.0485 (9)	0.0496 (9)	−0.0229 (7)	0.0022 (7)	−0.0214 (7)
N3	0.058 (1)	0.0384 (8)	0.0434 (9)	−0.0206 (7)	0.0035 (7)	−0.0110 (6)
N4	0.059 (1)	0.0396 (8)	0.0417 (9)	−0.0229 (7)	0.0003 (7)	−0.0146 (6)
C1	0.043 (1)	0.038 (1)	0.047 (1)	0.0006 (8)	−0.0128 (8)	−0.0096 (8)
C2	0.0272 (8)	0.049 (1)	0.048 (1)	−0.0082 (7)	0.0010 (7)	−0.0206 (8)
C3	0.0312 (8)	0.0399 (9)	0.0380 (9)	−0.0143 (7)	0.0002 (7)	−0.0114 (7)
C4	0.0288 (8)	0.0329 (8)	0.0362 (9)	−0.0098 (6)	0.0000 (6)	−0.0135 (7)
C5	0.046 (1)	0.0374 (9)	0.0350 (9)	−0.0174 (8)	0.0046 (7)	−0.0101 (7)
C6	0.052 (1)	0.0319 (9)	0.0327 (9)	−0.0129 (8)	−0.0029 (7)	−0.0040 (6)
C7	0.0396 (9)	0.0294 (8)	0.0360 (9)	−0.0108 (7)	0.0010 (7)	−0.0073 (6)
C8	0.0405 (9)	0.0307 (8)	0.0312 (8)	−0.0116 (7)	−0.0004 (6)	−0.0090 (6)
C9	0.041 (1)	0.046 (1)	0.041 (1)	−0.0179 (8)	0.0087 (7)	−0.0176 (7)
C10	0.0388 (9)	0.0309 (9)	0.049 (1)	−0.0086 (7)	−0.0059 (8)	−0.0092 (7)
C11	0.0380 (9)	0.0348 (9)	0.0404 (9)	−0.0071 (7)	−0.0043 (7)	−0.0018 (7)
C12	0.047 (1)	0.0337 (9)	0.0417 (9)	−0.0115 (8)	−0.0104 (8)	−0.0063 (7)
C13	0.063 (1)	0.051 (1)	0.065 (2)	0.007 (1)	−0.023 (1)	−0.012 (1)
C14	0.0400 (9)	0.0360 (9)	0.0396 (9)	−0.0146 (7)	−0.0001 (7)	−0.0148 (7)
C15	0.046 (1)	0.0344 (9)	0.0350 (9)	−0.0133 (7)	−0.0017 (7)	−0.0107 (7)
OW	0.0515 (8)	0.062 (1)	0.074 (1)	−0.0306 (7)	0.0046 (7)	−0.0305 (8)

Geometric parameters (Å, º) top

O1—C14	1.229 (2)	C5—H1C5	1.000
O2—C15	1.229 (2)	C5—H2C5	1.000
N1—N2	1.402 (2)	C6—C7	1.491 (2)
N1—C3	1.284 (2)	C6—HC6	1.000
N2—C14	1.333 (2)	C7—C8	1.503 (2)
N2—HN2	1.000	C8—C9	1.542 (2)
N3—N4	1.415 (2)	C8—C12	1.534 (2)
N3—C7	1.283 (2)	C8—C15	1.531 (2)
N4—C15	1.342 (3)	C9—H1C9	1.000
N4—HN4	1.000	C9—H2C9	1.000
C1—C2	1.533 (3)	C10—C11	1.438 (3)
C1—C6	1.543 (3)	C10—H1C10	1.000
C1—H1C1	1.000	C10—H2C10	1.000
C1—H2C1	1.000	C11—C12	1.380 (3)
C2—C3	1.490 (2)	C11—C13	1.510 (3)
C2—C9	1.540 (3)	C12—HC12	1.000
C2—HC2	1.000	C13—H1C13	1.000
C3—C4	1.507 (2)	C13—H2C13	1.000
C4—C5	1.550 (2)	C13—H3C13	1.000
C4—C10	1.528 (2)	OW—H1OW	1.000
C4—C14	1.535 (2)	OW—H2OW	1.000
C5—C6	1.543 (2)

N2—N1—C3	107.0 (1)	N3—C7—C6	121.8 (2)
N1—N2—C14	113.5 (1)	N3—C7—C8	113.9 (2)
N1—N2—HN2	123.2	C6—C7—C8	122.4 (2)
C14—N2—HN2	123.2	C7—C8—C9	112.6 (1)
N4—N3—C7	106.9 (2)	C7—C8—C12	112.7 (2)
N3—N4—C15	112.4 (1)	C7—C8—C15	99.0 (1)
N3—N4—HN4	123.8	C9—C8—C12	115.6 (2)
C15—N4—HN4	123.8	C9—C8—C15	112.0 (1)
C2—C1—C6	109.5 (1)	C12—C8—C15	103.3 (1)
C2—C1—H1C1	109.5	C2—C9—C8	114.2 (2)
C2—C1—H2C1	109.5	C2—C9—H1C9	108.3
C6—C1—H1C1	109.5	C2—C9—H2C9	108.3
C6—C1—H2C1	109.5	C8—C9—H1C9	108.3
H1C1—C1—H2C1	109.5	C8—C9—H2C9	108.3
C1—C2—C3	104.3 (2)	H1C9—C9—H2C9	109.5
C1—C2—C9	112.1 (2)	C4—C10—C11	127.5 (2)
C1—C2—HC2	108.2	C4—C10—H1C10	104.8
C3—C2—C9	115.7 (2)	C4—C10—H2C10	104.8
C3—C2—HC2	108.2	C11—C10—H1C10	104.8
C9—C2—HC2	108.2	C11—C10—H2C10	104.8
N1—C3—C2	120.9 (2)	H1C10—C10—H2C10	109.5
N1—C3—C4	113.8 (2)	C10—C11—C12	132.2 (2)
C2—C3—C4	122.7 (1)	C10—C11—C13	112.7 (2)
C3—C4—C5	111.0 (1)	C12—C11—C13	115.1 (2)
C3—C4—C10	115.8 (2)	C8—C12—C11	129.0 (2)
C3—C4—C14	98.9 (1)	C8—C12—HC12	115.5
C5—C4—C10	114.7 (1)	C11—C12—HC12	115.5
C5—C4—C14	111.9 (1)	C11—C13—H1C13	109.5
C10—C4—C14	103.2 (1)	C11—C13—H2C13	109.5
C4—C5—C6	114.4 (1)	C11—C13—H3C13	109.5
C4—C5—H1C5	108.2	H1C13—C13—H2C13	109.5
C4—C5—H2C5	108.2	H1C13—C13—H3C13	109.5
C6—C5—H1C5	108.2	H2C13—C13—H3C13	109.5
C6—C5—H2C5	108.2	O1—C14—N2	125.5 (2)
H1C5—C5—H2C5	109.5	O1—C14—C4	128.1 (2)
C1—C6—C5	111.6 (2)	N2—C14—C4	106.4 (1)
C1—C6—C7	103.6 (2)	O2—C15—N4	126.6 (2)
C1—C6—HC6	108.1	O2—C15—C8	127.0 (2)
C5—C6—C7	116.9 (1)	N4—C15—C8	106.3 (2)
C5—C6—HC6	108.1	H1OW—OW—H2OW	109.5
C7—C6—HC6	108.1

C3—N1—N2—C14	5.0 (2)	C5—C4—C10—H2C10	62.5
C3—N1—N2—HN2	−175.0	C14—C4—C10—C11	178.2 (2)
N2—N1—C3—C2	−162.8 (2)	C14—C4—C10—H1C10	55.8
N2—N1—C3—C4	−0.5 (2)	C14—C4—C10—H2C10	−59.5
N1—N2—C14—O1	174.6 (2)	C3—C4—C14—O1	−175.7 (2)
N1—N2—C14—C4	−7.0 (2)	C3—C4—C14—N2	5.9 (2)
HN2—N2—C14—O1	−5.4	C5—C4—C14—O1	−58.8 (3)
HN2—N2—C14—C4	173.0	C5—C4—C14—N2	122.8 (2)
C7—N3—N4—C15	8.1 (2)	C10—C4—C14—O1	65.0 (2)
C7—N3—N4—HN4	−171.9	C10—C4—C14—N2	−113.4 (2)
N4—N3—C7—C6	−164.3 (2)	C4—C5—C6—C1	47.2 (2)
N4—N3—C7—C8	0.2 (2)	C4—C5—C6—C7	−71.8 (2)
N3—N4—C15—O2	170.8 (2)	C4—C5—C6—HC6	166.0
N3—N4—C15—C8	−12.5 (2)	H1C5—C5—C6—C1	167.9
HN4—N4—C15—O2	−9.2	H1C5—C5—C6—C7	49.0
HN4—N4—C15—C8	167.5	H1C5—C5—C6—HC6	−73.3
C6—C1—C2—C3	62.4 (2)	H2C5—C5—C6—C1	−73.5
C6—C1—C2—C9	−63.5 (2)	H2C5—C5—C6—C7	167.5
C6—C1—C2—HC2	177.4	H2C5—C5—C6—HC6	45.3
H1C1—C1—C2—C3	−57.6	C1—C6—C7—N3	108.8 (2)
H1C1—C1—C2—C9	176.5	C1—C6—C7—C8	−54.4 (2)
H1C1—C1—C2—HC2	57.4	C5—C6—C7—N3	−128.1 (2)
H2C1—C1—C2—C3	−177.6	C5—C6—C7—C8	68.8 (2)
H2C1—C1—C2—C9	56.5	HC6—C6—C7—N3	−5.9
H2C1—C1—C2—HC2	−62.6	HC6—C6—C7—C8	−169.0
C2—C1—C6—C5	−63.1 (2)	N3—C7—C8—C9	−125.5 (2)
C2—C1—C6—C7	63.5 (2)	N3—C7—C8—C12	101.6 (2)
C2—C1—C6—HC6	178.1	N3—C7—C8—C15	−7.0 (2)
H1C1—C1—C6—C5	56.9	C6—C7—C8—C9	38.9 (2)
H1C1—C1—C6—C7	−176.5	C6—C7—C8—C12	−94.0 (2)
H1C1—C1—C6—HC6	−61.9	C6—C7—C8—C15	157.4 (2)
H2C1—C1—C6—C5	176.9	C7—C8—C9—C2	−30.6 (2)
H2C1—C1—C6—C7	−56.5	C7—C8—C9—H1C9	−151.3
H2C1—C1—C6—HC6	58.1	C7—C8—C9—H2C9	90.1
C1—C2—C3—N1	105.6 (2)	C12—C8—C9—C2	100.9 (2)
C1—C2—C3—C4	−55.1 (2)	C12—C8—C9—H1C9	−19.8
C9—C2—C3—N1	−130.8 (2)	C12—C8—C9—H2C9	−138.4
C9—C2—C3—C4	68.4 (2)	C15—C8—C9—C2	−141.2 (2)
HC2—C2—C3—N1	−9.4	C15—C8—C9—H1C9	98.2
HC2—C2—C3—C4	−170.1	C15—C8—C9—H2C9	−20.5
C1—C2—C9—C8	45.0 (2)	C7—C8—C12—C11	69.6 (3)
C1—C2—C9—H1C9	165.7	C7—C8—C12—HC12	−110.4
C1—C2—C9—H2C9	−75.7	C9—C8—C12—C11	−61.8 (3)
C3—C2—C9—C8	−74.4 (2)	C9—C8—C12—HC12	118.2
C3—C2—C9—H1C9	46.3	C15—C8—C12—C11	175.5 (2)
C3—C2—C9—H2C9	164.9	C15—C8—C12—HC12	−4.5
HC2—C2—C9—C8	164.1	C7—C8—C15—O2	−172.1 (2)
HC2—C2—C9—H1C9	−75.2	C7—C8—C15—N4	11.2 (2)
HC2—C2—C9—H2C9	43.4	C9—C8—C15—O2	−53.2 (3)
N1—C3—C4—C5	−120.9 (2)	C9—C8—C15—N4	130.1 (2)
N1—C3—C4—C10	106.1 (2)	C12—C8—C15—O2	71.9 (2)
N1—C3—C4—C14	−3.3 (2)	C12—C8—C15—N4	−104.9 (2)
C2—C3—C4—C5	41.1 (2)	C4—C10—C11—C12	−9.2 (3)
C2—C3—C4—C10	−91.9 (2)	C4—C10—C11—C13	172.8 (2)
C2—C3—C4—C14	158.7 (2)	H1C10—C10—C11—C12	113.2
C3—C4—C5—C6	−33.8 (2)	H1C10—C10—C11—C13	−64.9
C3—C4—C5—H1C5	−154.5	H2C10—C10—C11—C12	−131.6
C3—C4—C5—H2C5	87.0	H2C10—C10—C11—C13	50.4
C10—C4—C5—C6	99.7 (2)	C10—C11—C12—C8	−0.9 (4)
C10—C4—C5—H1C5	−21.0	C10—C11—C12—HC12	179.1
C10—C4—C5—H2C5	−139.5	C13—C11—C12—C8	177.1 (2)
C14—C4—C5—C6	−143.1 (1)	C13—C11—C12—HC12	−2.9
C14—C4—C5—H1C5	96.1	C10—C11—C13—H1C13	−180.0
C14—C4—C5—H2C5	−22.4	C10—C11—C13—H2C13	−60.0
C3—C4—C10—C11	71.3 (2)	C10—C11—C13—H3C13	60.0
C3—C4—C10—H1C10	−51.0	C12—C11—C13—H1C13	1.6
C3—C4—C10—H2C10	−166.3	C12—C11—C13—H2C13	121.6
C5—C4—C10—C11	−59.9 (2)	C12—C11—C13—H3C13	−118.4
C5—C4—C10—H1C10	177.7

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—HN2···OWⁱ	1.00	1.83	2.763 (3)	154
N4—HN4···O2ⁱⁱ	1.00	2.00	2.858 (2)	143
OW—H1OW···O1	1.00	1.85	2.844 (2)	169
OW—H2OW···O1ⁱⁱⁱ	1.00	1.81	2.796 (2)	169

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₆N₄O₂·H₂O
M_r	302.3
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	6.478 (1), 8.157 (1), 14.812 (2)
α, β, γ (°)	85.412 (9), 88.369 (8), 67.089 (11)
V (Å³)	718.6 (2)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.82
Crystal size (mm)	0.30 × 0.25 × 0.22

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	2695, 2695, 2365
R_int	?
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.089, 1.64
No. of reflections	2357
No. of parameters	200
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.22

Computer programs: CAD-4 (Schagen et al., 1989), SIR92 (Altomare et al., 1994), RAELS (Rae, 2000), ORTEPII (Johnson, 1976) and CrystalMaker (CrystalMaker Software, 2005), Local programs.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—HN2···OWⁱ	1.00	1.83	2.763 (3)	154
N4—HN4···O2ⁱⁱ	1.00	2.00	2.858 (2)	143
OW—H1OW···O1	1.00	1.85	2.844 (2)	169
OW—H2OW···O1ⁱⁱⁱ	1.00	1.81	2.796 (2)	169

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

Acknowledgements

This research was supported by the Australian Research Council.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. CrossRef Web of Science IUCr Journals Google Scholar
Chan, I. Y. H., Bishop, R., Craig, D. C., Scudder, M. L. & Yue, W. (2008). Acta Cryst. E64, o841. Web of Science CSD CrossRef IUCr Journals Google Scholar
CrystalMaker Software (2005). CrystalMaker. CrystalMaker Software, Bicester, Oxfordshire, England. www.CrystalMaker.co.uk. Google Scholar
Etter, M. C. (1990). Acc. Chem. Res. 23, 120–126. CrossRef CAS Web of Science Google Scholar
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Rae, A. D. (2000). RAELS. Australian National University, Canberra. Google Scholar
Schagen, J. D., Straver, L., van Meurs, F. & Williams, G. (1989). CAD-4 Manual. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Yue, W., Bishop, R., Craig, D. C. & Scudder, M. L. (2000). Tetrahedron, 56, 6667–6673. Web of Science CSD CrossRef CAS Google Scholar
Yue, W., Bishop, R., Craig, D. C. & Scudder, M. L. (2007). Acta Cryst. E63, o4689. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yue, W., Bishop, R., Scudder, M. L. & Craig, D. C. (1997). J. Chem. Soc., Perkin Trans. 1, pp. 2937–2946. Google Scholar

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Volume 64| Part 6| June 2008| Page o1055

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

5,7,9,10-Tetra­hydro-5β,10β-methano-3aα,8aα-methyl­propeno­cyclo­octa­[1,2-c:5,6-c′]di­pyrazole-3,8(2H,4H)-dione monohydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

5,7,9,10-Tetrahydro-5β,10β-methano-3aα,8aα-methylpropenocycloocta[1,2-c:5,6-c′]dipyrazole-3,8(2H,4H)-dione monohydrate