4,7-Phenanthrolinium perchlorate–5-methyl-1,2,4-triazolo[1,5-a]pyrimidin-7(4H)-one–water (1/1/2)

Caballero, A.B.; Quirós, M.; Salas, J.M.

doi:10.1107/S1600536810002564

organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Pages o459-o460

https://doi.org/10.1107/S1600536810002564

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4,7-Phenanthrolinium perchlorate–5-methyl-1,2,4-triazolo[1,5-a]pyrimidin-7(4H)-one–water (1/1/2)

Ana B. Caballero,^a Miguel Quirós ^a ^* and Juan M. Salas ^a

^aDepartamento de Química Inorgánica, Facultad de Ciencias, Universidad de Granada, 18071 Granada, Spain
^*Correspondence e-mail: mquiros@ugr.es

(Received 15 January 2010; accepted 20 January 2010; online 27 January 2010)

The asymmetric unit of the title compound, C₁₂H₉N₂⁺·ClO₄⁻·C₆H₆N₄O·2H₂O, contains a monoprotonated 4,7-phenanthrolinium (47phen) cation, a perchlorate anion balancing its charge, a neutral molecule of 5-methyl-1,2,4-triazolo[1,5-a]pyrimidin-7(4H)-one (HmtpO) and two interstitial water molecules. In the crystal structure, the acidic H atoms of 47phenH⁺ and HmtpO form strong hydrogen bonds with the water molecules, which in turn act as hydrogen-bond donors, forming links between them and towards the carbonyl O atom of HmtpO, the non-protonated N atom of 47phen⁺ and one of the O atoms of the anion.

Related literature

For other structures containing perchlorate and protonated 4,7-phenanthroline, see: Shang et al. (2006 ); Gillard et al. (1998 ). For other structures containing neutral and non-coordinated 5-methyl-1,2,4-triazolo[1,5-a]pyrimidin-7(4H)-one, see: Navarro et al. (1997 ); Salas et al. (1996 ).

Experimental

Crystal data

C₁₂H₉N₂⁺·ClO₄⁻·C₆H₆N₄O·2H₂O
M_r = 466.84
Monoclinic, P 2₁ /c
a = 8.6082 (8) Å
b = 14.7723 (14) Å
c = 16.8079 (17) Å
β = 104.609 (2)°
V = 2068.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 298 K
0.42 × 0.38 × 0.13 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ) T_min = 0.764, T_max = 0.969
12883 measured reflections
4653 independent reflections
3687 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.152
S = 1.03
4653 reflections
302 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯O2W	0.86	1.89	2.743 (2)	173
N4P—H4P⋯O1W	0.86	1.84	2.699 (3)	175
O1W—H11W⋯O7ⁱ	0.82 (1)	1.96 (2)	2.733 (3)	158 (3)
O1W—H12W⋯O2Wⁱⁱ	0.82 (1)	2.10 (1)	2.913 (3)	173 (3)
O2W—H21W⋯O3ⁱⁱⁱ	0.82 (1)	2.09 (1)	2.875 (3)	162 (3)
O2W—H22W⋯N7P^iv	0.82 (1)	1.96 (1)	2.771 (3)	177 (3)
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) x, y, z+1.

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Xtal_GX (Hall & du Boulay, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810002564/lh2981sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810002564/lh2981Isup2.hkl

checkCIF report

Comment top

The title compound was obtained as a by-product when trying to synthesize a copper complex containing both heterocycles, as indicated in the preparation section. The formula of the compound is (47phenH)(HmtpO)(ClO₄).2H₂O (47phen = 4,7-phenanthroline and HmtpO = 5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-7(4H)-one), which also correspond to the contents of the asymmetric unit which is shown in Figure 1. The geometrical parameters of both heterocycles do not significantly differ from other compounds with protonated 47phen (Shang et al., 2006, Gillard et al., 1998) or neutral HmtpO (Navarro et al., 1997, Salas et al. 1996). The species are linked in the crystal mainly by hydrogen bonds, water molecules being the main actors of the H-bond network. One of the independent water molecules (O1W) accepts an H-bond from the extra proton of 47phen (N4P—H) and donates towards the carbonyl O-atom (O7) of the triazolopyrimidine moiety and towards the other water molecule (O2W). The later also accepts an H-bond from the acidic H-atom of HmtpO (N4—H) acting as donor for the perchlorate anion and for the non-protonated N atom of 47phen (N7P). This builds a two-dimensional hydrogen bond network, which includes, among other motifs, centrosymmetric (HmtpO)₂(H₂O)₄ boxes, with both HmtpO molecules stacked with a separation of 3.4 Å and linked by two chains with two water molecules each, starting at N4P of one of the heterocycles and ending at O7 of the other: N4P—H···O1W—H···O2W—H···O7.

Related literature top

For other structures containing perchlorate and protonated 4,7-phenanthroline, see: Shang et al. (2006); Gillard et al. (1998). For structures containing neutral and non-coordinated 5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-7(4H)-one, see: Navarro et al. (1997); Salas et al. (1996).

Experimental top

The compound was fortuitously obtained as a by-product when trying to synthesize a ternary complex of Cu(II) with 5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-7(4H)-one (HmtpO) and 4,7-phenanthroline (47phen). An aqueous solution (10 ml.) of Cu(ClO₄)₂.6H₂O (0,75 g, 2 mmol), another aqueous solution (20 ml.) of HmtpO (0,61 g, 4 mmol) and a ethanolic solution (10 ml.) of 47phen (0,73 g, 4 mmol) were mixed and the mixture was refluxed for 2 h, a green precipitate (a Cu-Hmtpo complex) appearing which was filtered off. The mother liquor was left to stand at room temperature for two weeks, when a mixture of green and pale yellow crystals was obtained, which was filtered off. It was possible to separate both types of crystals under a lens, the green crystals turning out to be a Cu-phen complex whereas the pale yellow ones are the title compound, the structure of which is presented in this article. Elemental analysis data for C₁₈H₁₉ClN₆O₇. % Found (Calc.): C 46.17 (46.31), H 4.52 (4.10), N 17.79 (18.00).

Structure description top

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Xtal_GX (Hall & du Boulay, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. View of the asymmetric unit of the title compound with the displacement ellipsoids shown at the 50% probability level. Hydrogen bonds are shown as dashed lines.

4,7-Phenanthrolinium perchlorate–5-methyl-1,2,4-triazolo[1,5-a]pyrimidin-7(4H)-one– water (1/1/2) top

Crystal data top

C₁₂H₉N₂⁺·ClO₄⁻·C₆H₆N₄O·2H₂O	F(000) = 968
M_r = 466.84	D_x = 1.499 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3841 reflections
a = 8.6082 (8) Å	θ = 2.4–24.6°
b = 14.7723 (14) Å	µ = 0.24 mm⁻¹
c = 16.8079 (17) Å	T = 298 K
β = 104.609 (2)°	Irregular, pale yellow
V = 2068.2 (3) Å³	0.42 × 0.38 × 0.13 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	4653 independent reflections
Radiation source: fine-focus sealed tube	3687 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 8.26 pixels mm^-1	θ_max = 28.3°, θ_min = 1.9°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 1999)	k = −18→16
T_min = 0.764, T_max = 0.969	l = −22→13
12883 measured reflections

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)] = 0.054	Hydrogen site location: mixed
wR(F²) = 0.152	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.080P)² + 0.7P] where P = (F_o² + 2F_c²)/3
4653 reflections	(Δ/σ)_max = 0.001
302 parameters	Δρ_max = 0.40 e Å⁻³
4 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₂H₉N₂⁺·ClO₄⁻·C₆H₆N₄O·2H₂O	V = 2068.2 (3) Å³
M_r = 466.84	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.6082 (8) Å	µ = 0.24 mm⁻¹
b = 14.7723 (14) Å	T = 298 K
c = 16.8079 (17) Å	0.42 × 0.38 × 0.13 mm
β = 104.609 (2)°

Data collection top

Bruker SMART APEX CCD diffractometer	4653 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	3687 reflections with I > 2σ(I)
T_min = 0.764, T_max = 0.969	R_int = 0.029
12883 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	4 restraints
wR(F²) = 0.152	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.40 e Å⁻³
4653 reflections	Δρ_min = −0.37 e Å⁻³
302 parameters

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
Cl	0.45313 (6)	0.33264 (4)	0.31768 (3)	0.04631 (18)
O1	0.3034 (3)	0.31480 (17)	0.33511 (15)	0.0894 (7)
O2	0.4656 (3)	0.42667 (14)	0.30285 (15)	0.0838 (6)
O3	0.4615 (4)	0.28347 (18)	0.24717 (16)	0.1138 (10)
O4	0.5784 (3)	0.30880 (19)	0.38506 (17)	0.1111 (9)
N1	0.0430 (2)	0.68226 (12)	0.53673 (12)	0.0482 (5)
C2	0.0189 (3)	0.67004 (16)	0.61003 (16)	0.0521 (6)
H2	−0.0348	0.7130	0.6336	0.063*
N3	0.0760 (2)	0.59263 (13)	0.65035 (12)	0.0470 (4)
C3A	0.1429 (2)	0.55371 (13)	0.59692 (12)	0.0372 (4)
N4	0.2222 (2)	0.47442 (11)	0.60339 (10)	0.0390 (4)
H4	0.2287	0.4404	0.6456	0.047*
C5	0.2917 (3)	0.44833 (14)	0.54280 (13)	0.0416 (5)
C51	0.3840 (3)	0.36204 (17)	0.55767 (17)	0.0591 (6)
H51	0.4143	0.3444	0.5087	0.071*
H52	0.3184	0.3156	0.5725	0.071*
H53	0.4786	0.3704	0.6016	0.071*
C6	0.2757 (3)	0.49988 (15)	0.47456 (13)	0.0456 (5)
H6	0.3213	0.4791	0.4334	0.055*
C7	0.1924 (3)	0.58373 (15)	0.46251 (13)	0.0438 (5)
O7	0.1771 (2)	0.63513 (13)	0.40383 (10)	0.0629 (5)
N8	0.1250 (2)	0.60466 (11)	0.52801 (10)	0.0375 (4)
C1P	0.2195 (3)	0.60343 (16)	0.13977 (14)	0.0509 (6)
H1P	0.2555	0.6615	0.1325	0.061*
C1AP	0.2186 (2)	0.53636 (14)	0.08008 (12)	0.0388 (4)
C2P	0.1672 (3)	0.58385 (19)	0.20817 (15)	0.0608 (7)
H2P	0.1682	0.6283	0.2475	0.073*
C3P	0.1126 (3)	0.49785 (19)	0.21863 (15)	0.0565 (6)
H3P	0.0758	0.4847	0.2648	0.068*
N4P	0.1128 (2)	0.43452 (14)	0.16298 (11)	0.0480 (5)
H4P	0.0784	0.3814	0.1707	0.058*
C4AP	0.1650 (2)	0.44961 (14)	0.09408 (13)	0.0401 (5)
C5P	0.1638 (3)	0.37718 (15)	0.03805 (14)	0.0488 (5)
H5P	0.1270	0.3202	0.0482	0.059*
C6P	0.2157 (3)	0.39210 (15)	−0.02966 (14)	0.0501 (5)
H6P	0.2193	0.3440	−0.0648	0.060*
C6AP	0.2661 (2)	0.47963 (15)	−0.04881 (13)	0.0423 (5)
N7P	0.3086 (3)	0.48934 (14)	−0.12090 (12)	0.0548 (5)
C8P	0.3516 (3)	0.57049 (19)	−0.14009 (16)	0.0611 (7)
H8P	0.3800	0.5776	−0.1896	0.073*
C9P	0.3551 (3)	0.64575 (18)	−0.09078 (16)	0.0617 (7)
H9P	0.3864	0.7016	−0.1071	0.074*
C10P	0.3139 (3)	0.63783 (17)	−0.01789 (15)	0.0539 (6)
H10P	0.3155	0.6880	0.0157	0.065*
C0AP	0.2681 (2)	0.55214 (14)	0.00543 (13)	0.0397 (5)
O1W	0.0223 (2)	0.26333 (13)	0.18493 (13)	0.0679 (5)
H11W	−0.045 (3)	0.237 (2)	0.1499 (15)	0.081*
H12W	0.095 (3)	0.2279 (18)	0.2039 (19)	0.081*
O2W	0.2656 (3)	0.37456 (12)	0.74489 (11)	0.0640 (5)
H21W	0.335 (3)	0.3355 (16)	0.7542 (19)	0.077*
H22W	0.275 (4)	0.4077 (17)	0.7846 (13)	0.077*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.0445 (3)	0.0470 (3)	0.0486 (3)	−0.0056 (2)	0.0139 (2)	−0.0066 (2)
O1	0.0712 (13)	0.1078 (18)	0.1028 (18)	−0.0295 (12)	0.0472 (13)	−0.0301 (14)
O2	0.0952 (16)	0.0500 (11)	0.1048 (17)	−0.0044 (10)	0.0228 (14)	0.0031 (11)
O3	0.171 (3)	0.0986 (18)	0.1052 (18)	−0.0598 (18)	0.0961 (19)	−0.0507 (15)
O4	0.0844 (17)	0.1027 (19)	0.120 (2)	0.0050 (14)	−0.0229 (15)	0.0294 (16)
N1	0.0501 (11)	0.0397 (10)	0.0580 (12)	0.0076 (8)	0.0193 (9)	0.0062 (8)
C2	0.0545 (13)	0.0445 (12)	0.0642 (15)	0.0067 (10)	0.0273 (12)	−0.0001 (11)
N3	0.0546 (11)	0.0445 (10)	0.0475 (11)	0.0028 (8)	0.0232 (9)	0.0028 (8)
C3A	0.0364 (10)	0.0377 (10)	0.0383 (10)	−0.0050 (8)	0.0109 (8)	0.0017 (8)
N4	0.0458 (9)	0.0350 (9)	0.0354 (9)	0.0014 (7)	0.0089 (7)	0.0048 (7)
C5	0.0440 (11)	0.0378 (11)	0.0431 (11)	0.0009 (9)	0.0110 (9)	−0.0030 (9)
C51	0.0713 (16)	0.0464 (13)	0.0624 (15)	0.0156 (12)	0.0223 (13)	0.0041 (12)
C6	0.0550 (13)	0.0458 (12)	0.0388 (11)	0.0042 (10)	0.0174 (10)	−0.0018 (9)
C7	0.0468 (11)	0.0483 (12)	0.0363 (11)	0.0011 (9)	0.0109 (9)	0.0023 (9)
O7	0.0826 (13)	0.0654 (11)	0.0457 (9)	0.0198 (9)	0.0254 (9)	0.0208 (8)
N8	0.0400 (9)	0.0337 (8)	0.0385 (9)	0.0012 (7)	0.0094 (7)	0.0034 (7)
C1P	0.0661 (15)	0.0418 (12)	0.0479 (13)	0.0001 (11)	0.0200 (11)	−0.0025 (10)
C1AP	0.0404 (10)	0.0384 (11)	0.0378 (11)	0.0008 (8)	0.0101 (9)	0.0010 (8)
C2P	0.0820 (18)	0.0600 (15)	0.0460 (13)	0.0092 (13)	0.0266 (13)	−0.0063 (12)
C3P	0.0645 (15)	0.0705 (17)	0.0407 (12)	0.0067 (13)	0.0250 (11)	0.0086 (12)
N4P	0.0493 (10)	0.0505 (11)	0.0458 (11)	−0.0016 (8)	0.0153 (8)	0.0108 (9)
C4AP	0.0383 (10)	0.0419 (11)	0.0396 (11)	0.0020 (8)	0.0090 (9)	0.0051 (9)
C5P	0.0572 (13)	0.0363 (11)	0.0530 (13)	−0.0077 (10)	0.0140 (11)	0.0004 (10)
C6P	0.0644 (14)	0.0394 (12)	0.0474 (13)	−0.0040 (10)	0.0157 (11)	−0.0078 (10)
C6AP	0.0454 (11)	0.0429 (11)	0.0396 (11)	−0.0017 (9)	0.0127 (9)	−0.0007 (9)
N7P	0.0691 (13)	0.0574 (12)	0.0421 (11)	−0.0034 (10)	0.0217 (10)	−0.0055 (9)
C8P	0.0750 (17)	0.0690 (17)	0.0456 (13)	−0.0101 (14)	0.0271 (13)	0.0053 (12)
C9P	0.0794 (18)	0.0540 (14)	0.0570 (15)	−0.0140 (13)	0.0271 (14)	0.0073 (12)
C10P	0.0715 (16)	0.0418 (12)	0.0513 (13)	−0.0093 (11)	0.0210 (12)	−0.0009 (10)
C0AP	0.0405 (10)	0.0399 (11)	0.0390 (11)	−0.0018 (8)	0.0106 (9)	−0.0001 (9)
O1W	0.0710 (13)	0.0532 (11)	0.0702 (13)	−0.0163 (9)	0.0007 (10)	0.0043 (9)
O2W	0.1006 (15)	0.0453 (10)	0.0443 (10)	0.0124 (10)	0.0149 (10)	0.0037 (8)

Geometric parameters (Å, º) top

Cl—O4	1.398 (2)	C1AP—C0AP	1.442 (3)
Cl—O3	1.407 (2)	C2P—C3P	1.381 (4)
Cl—O1	1.416 (2)	C2P—H2P	0.9300
Cl—O2	1.420 (2)	C3P—N4P	1.323 (3)
N1—C2	1.313 (3)	C3P—H3P	0.9300
N1—N8	1.374 (2)	N4P—C4AP	1.362 (3)
C2—N3	1.357 (3)	N4P—H4P	0.8600
C2—H2	0.9300	C4AP—C5P	1.424 (3)
N3—C3A	1.315 (3)	C5P—C6P	1.341 (3)
C3A—N4	1.346 (3)	C5P—H5P	0.9300
C3A—N8	1.357 (3)	C6P—C6AP	1.426 (3)
N4—C5	1.361 (3)	C6P—H6P	0.9300
N4—H4	0.8600	C6AP—N7P	1.359 (3)
C5—C6	1.354 (3)	C6AP—C0AP	1.404 (3)
C5—C51	1.489 (3)	N7P—C8P	1.318 (3)
C51—H51	0.9600	C8P—C9P	1.382 (4)
C51—H52	0.9600	C8P—H8P	0.9300
C51—H53	0.9600	C9P—C10P	1.364 (3)
C6—C7	1.420 (3)	C9P—H9P	0.9300
C6—H6	0.9300	C10P—C0AP	1.411 (3)
C7—O7	1.225 (3)	C10P—H10P	0.9300
C7—N8	1.402 (3)	O1W—H11W	0.816 (10)
C1P—C2P	1.367 (3)	O1W—H12W	0.819 (10)
C1P—C1AP	1.409 (3)	O2W—H21W	0.818 (10)
C1P—H1P	0.9300	O2W—H22W	0.816 (10)
C1AP—C4AP	1.402 (3)

O4—Cl—O3	111.1 (2)	C4AP—C1AP—C0AP	118.41 (19)
O4—Cl—O1	110.00 (17)	C1P—C1AP—C0AP	123.79 (19)
O3—Cl—O1	108.70 (14)	C1P—C2P—C3P	119.8 (2)
O4—Cl—O2	108.15 (15)	C1P—C2P—H2P	120.1
O3—Cl—O2	109.56 (15)	C3P—C2P—H2P	120.1
O1—Cl—O2	109.35 (15)	N4P—C3P—C2P	119.9 (2)
C2—N1—N8	101.11 (17)	N4P—C3P—H3P	120.3
N1—C2—N3	117.5 (2)	C2P—C3P—H3P	119.8
N1—C2—H2	121.3	C3P—N4P—C4AP	123.0 (2)
N3—C2—H2	121.2	C3P—N4P—H4P	118.5
C3A—N3—C2	101.16 (18)	C4AP—N4P—H4P	118.5
N3—C3A—N4	128.72 (19)	N4P—C4AP—C1AP	119.04 (19)
N3—C3A—N8	111.43 (18)	N4P—C4AP—C5P	119.39 (19)
N4—C3A—N8	119.85 (17)	C1AP—C4AP—C5P	121.57 (19)
C3A—N4—C5	119.71 (17)	C6P—C5P—C4AP	119.3 (2)
C3A—N4—H4	120.1	C6P—C5P—H5P	120.4
C5—N4—H4	120.2	C4AP—C5P—H5P	120.3
C6—C5—N4	120.29 (19)	C5P—C6P—C6AP	121.7 (2)
C6—C5—C51	124.0 (2)	C5P—C6P—H6P	119.0
N4—C5—C51	115.68 (19)	C6AP—C6P—H6P	119.2
C5—C51—H51	109.7	N7P—C6AP—C0AP	122.4 (2)
C5—C51—H52	109.4	N7P—C6AP—C6P	117.6 (2)
H51—C51—H52	109.5	C0AP—C6AP—C6P	119.99 (19)
C5—C51—H53	109.4	C8P—N7P—C6AP	118.0 (2)
H51—C51—H53	109.5	N7P—C8P—C9P	123.3 (2)
H52—C51—H53	109.5	N7P—C8P—H8P	118.3
C5—C6—C7	123.46 (19)	C9P—C8P—H8P	118.3
C5—C6—H6	118.2	C10P—C9P—C8P	119.9 (2)
C7—C6—H6	118.3	C10P—C9P—H9P	120.1
O7—C7—N8	120.9 (2)	C8P—C9P—H9P	120.0
O7—C7—C6	127.1 (2)	C9P—C10P—C0AP	118.7 (2)
N8—C7—C6	111.98 (18)	C9P—C10P—H10P	120.6
C3A—N8—N1	108.82 (16)	C0AP—C10P—H10P	120.6
C3A—N8—C7	124.57 (17)	C6AP—C0AP—C10P	117.58 (19)
N1—N8—C7	126.40 (17)	C6AP—C0AP—C1AP	118.92 (19)
C2P—C1P—C1AP	120.4 (2)	C10P—C0AP—C1AP	123.5 (2)
C2P—C1P—H1P	119.8	H11W—O1W—H12W	108 (3)
C1AP—C1P—H1P	119.8	H21W—O2W—H22W	111 (3)
C4AP—C1AP—C1P	117.80 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O2W	0.86	1.89	2.743 (2)	173
N4P—H4P···O1W	0.86	1.84	2.699 (3)	175
O1W—H11W···O7ⁱ	0.82 (1)	1.96 (2)	2.733 (3)	158 (3)
O1W—H12W···O2Wⁱⁱ	0.82 (1)	2.10 (1)	2.913 (3)	173 (3)
O2W—H21W···O3ⁱⁱⁱ	0.82 (1)	2.09 (1)	2.875 (3)	162 (3)
O2W—H22W···N7P^iv	0.82 (1)	1.96 (1)	2.771 (3)	177 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₂H₉N₂⁺·ClO₄⁻·C₆H₆N₄O·2H₂O
M_r	466.84
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	8.6082 (8), 14.7723 (14), 16.8079 (17)
β (°)	104.609 (2)
V (Å³)	2068.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.42 × 0.38 × 0.13

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.764, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	12883, 4653, 3687
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.152, 1.03
No. of reflections	4653
No. of parameters	302
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.37

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Xtal_GX (Hall & du Boulay, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O2W	0.86	1.89	2.743 (2)	172.8
N4P—H4P···O1W	0.86	1.84	2.699 (3)	174.5
O1W—H11W···O7ⁱ	0.816 (10)	1.960 (16)	2.733 (3)	158 (3)
O1W—H12W···O2Wⁱⁱ	0.819 (10)	2.098 (11)	2.913 (3)	173 (3)
O2W—H21W···O3ⁱⁱⁱ	0.818 (10)	2.086 (14)	2.875 (3)	162 (3)
O2W—H22W···N7P^iv	0.816 (10)	1.956 (10)	2.771 (3)	177 (3)

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

Acknowledgements

We acknowledge financial support from the Spanish Ministerio de Ciencia y Tecnología (project CTQ2008–00037/PPQ) and from the Junta de Andalucía (research group FQM 195). ABC is grateful for a FPU grant from the Spanish Ministerio de Educación y Ciencia.

References

Bruker (1999). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Winsconsin, USA. Google Scholar
Gillard, R. D., Hursthouse, M. B., Abdul-Malik, K. M. & Paisey, S. (1998). J. Chem. Crystallogr. 28, 611–619. Web of Science CSD CrossRef CAS Google Scholar
Hall, S. R. & du Boulay, D. (1997). Xtal_GX. University of Western Australia, Perth, Australia. Google Scholar
Navarro, J. A. R., Romero, M. A., Salas, J. M., Faure, R. & Solans, X. (1997). J. Chem. Soc. Dalton Trans. pp. 2321–2326. CSD CrossRef Web of Science Google Scholar
Salas, J. M., Romero, M. A., Rodríguez, J. A. & Faure, R. (1996). J. Chem. Crystallogr. 26, 847–851. CSD CrossRef CAS Web of Science Google Scholar
Shang, R.-L., Du, L. & Sun, B.-W. (2006). Acta Cryst. E62, o2920–o2921. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 66| Part 2| February 2010| Pages o459-o460

https://doi.org/10.1107/S1600536810002564

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4,7-Phenanthrolinium perchlorate–5-methyl-1,2,4-triazolo[1,5-a]pyrimidin-7(4H)-one–water (1/1/2)

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