Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
In the title compound, [Ca(C9H11N6O5)2(H2O)3], the Ca atom lies on a twofold rotation axis in C2/c and the three water mol­ecules are all disordered, each over two sites having equal occupancy. The anion acts as a bridging ligand between pairs of Ca sites on the same twofold axis, thus forming a one-dimensional coordination polymer, with the chains lying along the twofold axes. These chains are linked by multiple O—H...O and N—H...O hydrogen bonds into a single three-dimensional framework.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101004267/gg1048sup1.cif
Contains datablocks global, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101004267/gg1048IIsup2.hkl
Contains datablock II

CCDC reference: 166962

Comment top

The potassium salt of the pyrimidylglycylglycine [(I), LH] crystallizes as a monohydrate, K+L-·H2O, in which the cations and anions form a three-dimensional coordination polymer network, where the water molecules play no significant structural role (Low, Arranz et al., 2001). By contrast, in the calcium salt, which crystallizes as the trihydrate Ca2+(L-)2·3H2O, (II), the cations and anions form a one-dimensional coordination polymer; the individual strands of this polymer are connected into a single three-dimensional framework by means of a series of hydrogen bonds, dominated by those formed by the water molecules.

Compound (II) crystallizes in space group C2/c with Z' = 0.5; the Ca atom lies on a twofold rotation axis, selected for convenience to be that along (1/2, y, 1/4) with the anion in a general position. There are three water molecules coordinated to the calcium, each disordered over two sites with equal occupancy (Fig. 1). The water molecules can only adopt one of the two possible arrangements about the Ca2+ through geometry considerations, in order to avoid unacceptably short O···O distances between water molecules bound to the same Ca [O1···O2i 1.802 (7) Å and O3···O2i 1.289 (6) Å; symmetry code: (i) 1 - x, y, 0.5 - z].

The Ca atom is also coordinated by four O atoms, two carboxylic acid and two amidic, each from a different anionic ligand (Table 1 and Fig. 2), and the resulting CaO4 unit can be described as a slight distortion of square planar towards tetrahedral. Overall, the coordination geometry at calcium, including the three water molecules, is distorted pentagonal bipyramidal (Fig. 3). The Ca—O distances involving water span those involving the anionic ligands (Table 1); the carboxylate distance Ca—O23 is, unexpectedly, longer than the amidic distance Ca—O21. This coordination behaviour of the anion L- towards calcium may be contrasted with its behaviour towards potassium where, in addition to all three of the O atoms in the glycylglycinate side chain, the nitrosyl O5 atom also acts as one of the ligating atoms (Low, Arranz et al., 2001). The mean value of the Ca—O distances is 2.420 (4) Å; if the outlier value for the rather weakly bound O1 is omitted, the mean value of the other six Ca—O distances is 2.377 (4) Å; the mean value of the K—O distances in the analogous K+L-·H2O is 2.731 (2) Å (Low, Arranz et al., 2001). The difference between the mean Ca—O and K—O distances, ca 0.31 Å if Ca is regarded as seven-coordinate or ca 0.35 Å if it is regarded as six-coordinate, precisely reflect the differences between the corresponding ionic radii, as tabulated by Shannon & Prewitt (1970): K+ (six-coordinate) 1.38, Ca2+ (seven-coordinate) 1.07 and Ca2+ (six-coordinate) 1.00 Å.

The supramolecular structure can be most readily analysed and described using the substructure approach (Gregson et al., 2000). Each anion acts as a bridging ligand between adjacent Ca centres on a given twofold axis, thus generating a chain of 14-membered rings, fused in spiro fashion at the Ca atom (Fig. 2). Four of these chains run through each unit cell, along the lines (1/2, y, 1/4), (1/2, y, 3/4), (1, y, 1/4) and (1, y, 3/4), and each chain is linked to four neighbouring chains by means of O—H···O hydrogen bonds in which the coordinated water molecules act as the donors (Table 2). It is necessary to emphasize at this point, in respect of the disorder of the water sites, that although the site occupancies are fully correlated at each individual Ca centre, as described earlier, there are no such constraints on the water-site occupancies at neighbouring Ca sites along a chain, or on those at Ca sites in different chains.

The water O1 atom at (x, y, z) acts as hydrogen-bond donor, via H1AW, forming a rather long weak hydrogen bond, to O22 at (1 - x, y, 0.5 - z), which is part of the same [010] chain; similarly O3 at (x, y, z) acts as donor, via H3AW, to O22 at (1 - x, 1 + y, 0.5 - z), also part of the same chain. The other four O—H···O hydrogen bonds all serve to link adjacent chains. The water O2 atom at (x, y, z) is a component of the chain along (1/2, y, 1/4); O2 acts as hydrogen-bond donor, via H2AW, to O22 at (1.5 - x, 0.5 + y, 0.5 - z), which is a component of the chain along (1, y, 1/4), and it also acts as hydrogen-bond donor, via H2BW, to O5 at (x, -y, 0.5 + z), which is a component of the chain along (1/2, y, 3/4). Propagation by the space group of the these two interchain O—H···O hydrogen bonds, both formed by the water O2 atom, would of itself be sufficient to link all of the chains into a single framework. There are, however, several more hydrogen bonds which further reinforce the links between the chains. The water O3 atom at (x, y, z) acts as donor, via H3BW, to O22 at (-0.5 + x, 0.5 + y, z), which is a component of the chain along (0, y, 1/4), and the water O1 atom at (x, y, z) acts as donor, via H1BW and in a rather weak hydrogen bond, to O5 at (1 - x, -y, -z), a component of the chain along (1/2, y, -0.25). Thus, by means of these four O—H···O hydrogen bonds, the reference chain along (1/2, y, 1/4) is directly linked to those along (1/2, y, -0.25) and (1/2, y, 3/4) and to those along (1, y, 1/4) and (0, y, 1/4). Three hydrogen bonds with N—H donors provide further links (Table 2); N21 at (x, y, z) in the chain along (1/2, y, 1/4) acts as donor to O23 at (0.5 + x, 0.5 + y, z) in the chain along (1, y, 1/4), while N6 at (x, y, z) acts as donor, via H6A, to O4 at (-0.5 + x, 0.5 + y, z) in the chain along (0, y, 1/4), and finally, N22 at (x, y, z) forms a rather weaker hydrogen bond to N5 at (1.5 - x, -0.5 - y, -z), a component of the chain along (1, y, -0.25). Each Ca(H2O)3 unit along each chain gives rise to a similar set of hydrogen bonds, hence tying all the metal–anion chains into a single bundle.

The bond distances (Table 1) within the heterocyclic ring show evidence of a marked polarization of the electronic structure of this ring, as noted in previous studies (Low et al., 2000; Low, Moreno Sánchez et al., 2001; Low, Arranz et al., 2001). In particular, the C2—N1 bond is the longest of the C—N bonds in the sequence N2—C2—N1—C6—N6, although it is the only such bond which is represented as a double bond in the conventional representation (IIIa); bonds C4—C5 and C5—C6, respectively single and double bonds in form (IIIa), do not differ significantly in length, and the difference between the C5—N5 and N5—O5 nitroso distances is far smaller than expected from (IIIa) (Low et al., 2000). All of these observations point to the importance of the polarized form (IIIb), confirmed by the behaviour of O5 as a hydrogen-bond acceptor.

In the glycylglycinate side chain, the two C—O distances in the carboxylate group are very similar, and the amidic C—O distance is identical, within experimental uncertainty, to the amidic distance C4—O4. The conformation of the side chain (Table 1), which shows some unexpected torsion angles, is probably largely determined by combination of the requirements of O21 and O23 in coordinating to different Ca sites, and the extensive hydrogen bonding involving both donor and acceptor sites in the side chain.

Related literature top

For related literature, see: Gregson et al. (2000); Low et al. (2000, 2001); Shannon & Prewitt (1970).

Experimental top

Crystals of compound (II) were obtained adventitiously during preparation of the potassium salt derived from the ligand HL, (I) (Low, Arranz et al., 2001).

Refinement top

Compound (II) crystallized in the monoclinic system. Space groups Cc and C2/c were permitted by the systematic absences; C2/c was chosen and confirmed by the successful structure analysis. H atoms were treated as riding atoms with C—H distances of 0.98 (CH2) or 0.99 Å (CH3), and an N—H distance of 0.88 Å. Water molecules were initially handled via DFIX with an O—H distance of 0.87 (3) Å, and after this refinement had fully converged, the H atoms were treated as riding atoms using AFIX.

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) PRPKAPPA (Ferguson, 1999).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of compound (II) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Part of the crystal structure of (II) showing the formation of the one of the [010] chains formed by the cations and anions. For the sake of clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk (*), hash (#) or dollar sign ($) are at the symmetry positions (1 - x, y, 0.5 - z), (x, 1 + y, z), and (1 - x, 1 + y, 0.5 - z), respectively.
[Figure 3] Fig. 3. Part of the crystal structure of (II) showing the coordination at calcium. Atoms marked with an asterisk (*), hash (#) or dollar sign ($) are at the symmetry positions (1 - x, y, 0.5 - z), (x, 1 + y, z), and (1 - x, 1 + y, 0.5 - z), respectively. Only one set of positions for O1, O2 and O3 is shown (see text).
Triaqua-bis[N-(6-amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidin-2- yl)glycylglycinato]calcium top
Crystal data top
[Ca(C9H11N6O5)2(H2O)3]F(000) = 1376
Mr = 660.60Dx = 1.708 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 12.7815 (7) ÅCell parameters from 2553 reflections
b = 7.7010 (7) Åθ = 1.6–26.3°
c = 26.271 (2) ŵ = 0.34 mm1
β = 96.418 (5)°T = 150 K
V = 2569.7 (4) Å3Plate, colourless
Z = 40.15 × 0.08 × 0.01 mm
Data collection top
KappaCCD
diffractometer
2553 independent reflections
Radiation source: fine-focus sealed X-ray tube1641 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.090
ϕ scans, and ω scans with κ offsetsθmax = 26.3°, θmin = 1.6°
Absorption correction: multi-scan
)SORTAV; Blessing, 1995, 1997)
h = 1515
Tmin = 0.951, Tmax = 0.997k = 99
17345 measured reflectionsl = 3232
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0683P)2 + 1.8308P]
where P = (Fo2 + 2Fc2)/3
2553 reflections(Δ/σ)max < 0.001
214 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
[Ca(C9H11N6O5)2(H2O)3]V = 2569.7 (4) Å3
Mr = 660.60Z = 4
Monoclinic, C2/cMo Kα radiation
a = 12.7815 (7) ŵ = 0.34 mm1
b = 7.7010 (7) ÅT = 150 K
c = 26.271 (2) Å0.15 × 0.08 × 0.01 mm
β = 96.418 (5)°
Data collection top
KappaCCD
diffractometer
2553 independent reflections
Absorption correction: multi-scan
)SORTAV; Blessing, 1995, 1997)
1641 reflections with I > 2σ(I)
Tmin = 0.951, Tmax = 0.997Rint = 0.090
17345 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.135H-atom parameters constrained
S = 1.00Δρmax = 0.32 e Å3
2553 reflectionsΔρmin = 0.36 e Å3
214 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Ca10.50000.26170 (14)0.25000.0340 (3)
N10.71309 (17)0.0713 (3)0.04356 (9)0.0232 (6)
C20.80029 (19)0.0093 (4)0.07061 (11)0.0211 (6)
N210.81256 (17)0.0356 (3)0.12074 (9)0.0235 (6)
H210.86750.01020.13910.028*
O210.57497 (16)0.1272 (3)0.18061 (9)0.0366 (6)
C210.7382 (2)0.1377 (4)0.14670 (11)0.0247 (7)
H21A0.71760.24060.12530.030*
H21B0.77520.18040.17940.030*
N220.62534 (18)0.1190 (3)0.14391 (9)0.0250 (6)
H22A0.67350.16740.12710.030*
C220.6389 (2)0.0455 (4)0.15817 (11)0.0235 (7)
C230.5362 (2)0.2237 (4)0.15430 (12)0.0280 (7)
H23A0.50350.27450.12170.034*
H23B0.48320.14770.16780.034*
C240.5645 (2)0.3702 (4)0.19252 (11)0.0239 (7)
O220.64762 (16)0.3587 (3)0.22229 (9)0.0432 (6)
O230.49875 (14)0.4923 (3)0.19159 (7)0.0271 (5)
N30.87758 (16)0.0826 (3)0.04927 (9)0.0207 (5)
C30.9703 (2)0.1513 (4)0.08167 (11)0.0282 (7)
H3A1.02020.05680.09080.042*
H3B1.00430.24090.06280.042*
H3C0.94780.20190.11290.042*
C40.8704 (2)0.1138 (4)0.00318 (11)0.0225 (7)
O40.94132 (14)0.1910 (3)0.02184 (8)0.0281 (5)
C50.7752 (2)0.0524 (4)0.03337 (11)0.0210 (6)
N50.76720 (18)0.0941 (3)0.08314 (9)0.0274 (6)
O50.68578 (15)0.0401 (3)0.11212 (8)0.0350 (6)
C60.6993 (2)0.0414 (4)0.00688 (11)0.0222 (6)
N60.61208 (17)0.0987 (3)0.03334 (10)0.0300 (6)
H6A0.56490.15480.01770.036*
H6B0.60120.08070.06660.036*
O10.3833 (3)0.0182 (6)0.22220 (19)0.0398 (11)0.50
H1AW0.36380.11570.23750.048*0.50
H1BW0.32860.01230.20060.048*0.50
O20.6553 (3)0.1986 (6)0.29770 (16)0.0276 (10)0.50
H2AW0.71640.18920.28640.033*0.50
H2BW0.65350.14040.32520.033*0.50
O30.3257 (3)0.3417 (6)0.22504 (19)0.0392 (12)0.50
H3AW0.32470.44610.23950.047*0.50
H3BW0.26200.29780.22620.047*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ca10.0218 (5)0.0597 (7)0.0204 (5)0.0000.0022 (3)0.000
N10.0210 (12)0.0223 (14)0.0265 (14)0.0006 (10)0.0037 (10)0.0018 (11)
C20.0208 (14)0.0181 (16)0.0244 (17)0.0019 (11)0.0034 (11)0.0021 (13)
N210.0234 (12)0.0216 (14)0.0255 (14)0.0006 (10)0.0023 (10)0.0024 (11)
O210.0330 (12)0.0258 (13)0.0532 (15)0.0019 (10)0.0148 (10)0.0049 (11)
C210.0299 (16)0.0206 (17)0.0241 (16)0.0027 (12)0.0054 (12)0.0004 (13)
N220.0269 (13)0.0185 (15)0.0304 (15)0.0013 (10)0.0068 (10)0.0004 (11)
C220.0254 (15)0.0223 (18)0.0223 (16)0.0034 (12)0.0006 (12)0.0034 (13)
C230.0228 (15)0.0246 (18)0.0359 (18)0.0032 (12)0.0002 (12)0.0023 (14)
C240.0247 (16)0.0283 (18)0.0196 (16)0.0002 (13)0.0063 (12)0.0026 (13)
O220.0295 (12)0.0566 (17)0.0406 (14)0.0149 (11)0.0089 (10)0.0194 (12)
O230.0316 (11)0.0249 (12)0.0246 (12)0.0058 (9)0.0028 (8)0.0007 (9)
N30.0190 (12)0.0206 (14)0.0221 (13)0.0017 (9)0.0009 (9)0.0010 (10)
C30.0283 (16)0.0289 (18)0.0258 (17)0.0086 (13)0.0038 (12)0.0006 (14)
C40.0219 (15)0.0191 (16)0.0266 (17)0.0019 (12)0.0034 (12)0.0009 (13)
O40.0257 (11)0.0316 (13)0.0275 (12)0.0082 (9)0.0049 (8)0.0006 (10)
C50.0211 (14)0.0174 (16)0.0244 (17)0.0006 (11)0.0023 (11)0.0021 (13)
N50.0286 (13)0.0243 (15)0.0284 (15)0.0000 (10)0.0006 (11)0.0021 (12)
O50.0367 (12)0.0357 (14)0.0296 (13)0.0035 (10)0.0092 (9)0.0003 (10)
C60.0216 (14)0.0173 (16)0.0275 (17)0.0014 (11)0.0015 (11)0.0015 (13)
N60.0251 (13)0.0320 (16)0.0317 (15)0.0088 (11)0.0016 (11)0.0011 (12)
O10.042 (3)0.036 (3)0.039 (3)0.006 (2)0.003 (2)0.000 (2)
O20.019 (2)0.038 (3)0.026 (2)0.0005 (18)0.0038 (16)0.013 (2)
O30.030 (2)0.037 (3)0.049 (3)0.005 (2)0.002 (2)0.000 (3)
Geometric parameters (Å, º) top
Ca1—O12.676 (4)C22—O211.232 (3)
Ca1—O22.278 (4)C22—N221.327 (4)
Ca1—O32.334 (4)N22—C231.447 (4)
Ca1—O212.388 (2)C23—C241.526 (4)
Ca1—O23i2.437 (2)C24—O221.250 (3)
Ca1—O1ii2.676 (4)C24—O231.260 (3)
Ca1—O2ii2.278 (4)N21—H210.88
Ca1—O3ii2.334 (4)C21—H21A0.99
Ca1—O21ii2.388 (2)C21—H21B0.99
Ca1—O23iii2.437 (2)N22—H22A0.88
N1—C21.341 (3)C23—H23A0.99
C2—N31.384 (3)C23—H23B0.99
N3—C41.392 (4)C3—H3A0.98
C4—C51.455 (4)C3—H3B0.98
C5—C61.449 (4)C3—H3C0.98
C6—N11.337 (4)N6—H6A0.88
C2—N211.324 (4)N6—H6B0.88
N3—C31.477 (3)O1—H1AW0.90
C4—O41.231 (3)O1—H1BW0.88
C5—N51.339 (4)O2—H2AW0.87
N5—O51.288 (3)O2—H2BW0.85
C6—N61.322 (3)O3—H3AW0.89
N21—C211.460 (4)O3—H3BW0.89
C21—C221.513 (4)
O21—Ca1—O21ii128.61 (11)O21—C22—C21118.1 (3)
O23i—Ca1—O23iii77.97 (10)N22—C22—C21118.5 (3)
O21—Ca1—O23i80.29 (7)N22—C23—C24113.7 (2)
O21—Ca1—O23iii147.44 (7)N22—C23—H23A108.8
O1—Ca1—O2113.79 (16)C24—C23—H23A108.8
O1—Ca1—O369.53 (15)N22—C23—H23B108.8
O2—Ca1—O3163.04 (16)C24—C23—H23B108.8
O21—Ca1—O172.63 (12)H23A—C23—H23B107.7
O21—Ca1—O285.89 (12)O22—C24—O23125.7 (3)
O21—Ca1—O3110.60 (13)O22—C24—C23118.8 (3)
O23i—Ca1—O1119.34 (11)O23—C24—C23115.5 (2)
O23i—Ca1—O2117.14 (12)C24—O23—Ca1iv127.65 (17)
O23i—Ca1—O371.28 (13)C2—N3—C4121.2 (2)
O2ii—Ca1—O2183.50 (11)C2—N3—C3120.8 (2)
O3ii—Ca1—O2182.93 (13)C4—N3—C3117.9 (2)
O2—Ca1—O21ii83.50 (11)N3—C3—H3A109.5
O3—Ca1—O21ii82.93 (13)N3—C3—H3B109.5
O2ii—Ca1—O23i82.83 (12)H3A—C3—H3B109.5
O3ii—Ca1—O23i84.87 (13)N3—C3—H3C109.5
O21ii—Ca1—O23i147.44 (7)H3A—C3—H3C109.5
O2—Ca1—O23iii82.83 (12)H3B—C3—H3C109.5
O3—Ca1—O23iii84.87 (13)O4—C4—N3120.5 (2)
O21ii—Ca1—O166.43 (12)O4—C4—C5123.2 (3)
O23iii—Ca1—O1139.65 (11)N3—C4—C5116.3 (2)
O21—Ca1—O1ii66.43 (12)N5—C5—C6127.3 (2)
O23i—Ca1—O1ii139.65 (11)N5—C5—C4115.0 (2)
C6—N1—C2118.3 (2)C6—C5—C4117.7 (2)
N21—C2—N1118.1 (2)O5—N5—C5117.9 (2)
N21—C2—N3118.1 (2)N6—C6—N1118.3 (3)
N1—C2—N3123.8 (3)N6—C6—C5119.0 (3)
C2—N21—C21122.4 (2)N1—C6—C5122.7 (2)
C2—N21—H21118.8C6—N6—H6A120.0
C21—N21—H21118.8C6—N6—H6B120.0
C22—O21—Ca1158.5 (2)H6A—N6—H6B120.0
N21—C21—C22116.4 (2)Ca1—O1—H1AW136
N21—C21—H21A108.2Ca1—O1—H1BW110
C22—C21—H21A108.2H1AW—O1—H1BW106
N21—C21—H21B108.2Ca1—O2—H2AW126
C22—C21—H21B108.2Ca1—O2—H2BW118
H21A—C21—H21B107.3H2AW—O2—H2BW111
C22—N22—C23124.0 (2)Ca1—O3—H3AW100
C22—N22—H22A118.0Ca1—O3—H3BW138
C23—N22—H22A118.0H3AW—O3—H3BW106
O21—C22—N22123.3 (3)
C6—N1—C2—N21178.5 (2)O22—C24—O23—Ca1iv4.9 (4)
C6—N1—C2—N30.6 (4)C23—C24—O23—Ca1iv173.51 (18)
N1—C2—N21—C213.8 (4)N21—C2—N3—C4179.4 (2)
O2ii—Ca1—O21—C22150.5 (6)N1—C2—N3—C41.5 (4)
O2—Ca1—O21—C227.2 (6)N21—C2—N3—C30.8 (4)
O3ii—Ca1—O21—C2239.7 (6)N1—C2—N3—C3178.3 (3)
O3—Ca1—O21—C22168.7 (5)C2—N3—C4—O4177.7 (3)
O21ii—Ca1—O21—C2271.1 (5)C3—N3—C4—O42.5 (4)
O23i—Ca1—O21—C22125.7 (5)C2—N3—C4—C53.1 (4)
O23iii—Ca1—O21—C2277.0 (6)C3—N3—C4—C5176.7 (2)
O1—Ca1—O21—C22109.3 (6)O4—C4—C5—N53.4 (4)
O1ii—Ca1—O21—C2231.0 (5)N3—C4—C5—N5175.8 (2)
Ca1—O21—C22—N22102.7 (5)O4—C4—C5—C6178.1 (3)
Ca1—O21—C22—C2176.9 (6)N3—C4—C5—C62.7 (4)
C23—N22—C22—O212.1 (4)C6—C5—N5—O53.2 (4)
N21—C21—C22—O21179.1 (2)C4—C5—N5—O5178.5 (2)
N3—C2—N21—C21177.1 (2)C2—N1—C6—N6178.3 (2)
C2—N21—C21—C2280.8 (3)C2—N1—C6—C50.9 (4)
N21—C21—C22—N220.5 (4)N5—C5—C6—N61.7 (4)
C21—C22—N22—C23177.5 (3)C4—C5—C6—N6180.0 (3)
C22—N22—C23—C24111.7 (3)N5—C5—C6—N1177.5 (3)
N22—C23—C24—O2221.3 (4)C4—C5—C6—N10.8 (4)
N22—C23—C24—O23160.1 (2)
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z+1/2; (iii) x+1, y+1, z+1/2; (iv) x, y1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1AW···O22ii0.902.163.048 (5)168
O1—H1BW···O5v0.882.322.962 (5)130
O2—H2AW···O22vi0.871.822.667 (4)166
O2—H2BW···O5vii0.851.822.655 (5)164
O3—H3AW···O22iii0.891.822.692 (5)166
O3—H3BW···O22viii0.891.892.744 (5)162
N6—H6B···O50.881.942.598 (3)131
N6—H6A···O4viii0.881.972.761 (3)149
N21—H21···O23ix0.882.052.861 (3)152
N22—H22A···N5x0.882.343.132 (3)150
Symmetry codes: (ii) x+1, y, z+1/2; (iii) x+1, y+1, z+1/2; (v) x+1, y, z; (vi) x+3/2, y+1/2, z+1/2; (vii) x, y, z+1/2; (viii) x1/2, y+1/2, z; (ix) x+1/2, y+1/2, z; (x) x+3/2, y1/2, z.

Experimental details

Crystal data
Chemical formula[Ca(C9H11N6O5)2(H2O)3]
Mr660.60
Crystal system, space groupMonoclinic, C2/c
Temperature (K)150
a, b, c (Å)12.7815 (7), 7.7010 (7), 26.271 (2)
β (°) 96.418 (5)
V3)2569.7 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.34
Crystal size (mm)0.15 × 0.08 × 0.01
Data collection
DiffractometerKappaCCD
diffractometer
Absorption correctionMulti-scan
)SORTAV; Blessing, 1995, 1997)
Tmin, Tmax0.951, 0.997
No. of measured, independent and
observed [I > 2σ(I)] reflections
17345, 2553, 1641
Rint0.090
(sin θ/λ)max1)0.623
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.135, 1.00
No. of reflections2553
No. of parameters214
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.32, 0.36

Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXS97 (Sheldrick, 1997), PLATON (Spek, 2001), SHELXL97 (Sheldrick, 1997) PRPKAPPA (Ferguson, 1999).

Selected geometric parameters (Å, º) top
Ca1—O12.676 (4)C4—O41.231 (3)
Ca1—O22.278 (4)C5—N51.339 (4)
Ca1—O32.334 (4)N5—O51.288 (3)
Ca1—O212.388 (2)C6—N61.322 (3)
Ca1—O23i2.437 (2)N21—C211.460 (4)
N1—C21.341 (3)C21—C221.513 (4)
C2—N31.384 (3)C22—O211.232 (3)
N3—C41.392 (4)C22—N221.327 (4)
C4—C51.455 (4)N22—C231.447 (4)
C5—C61.449 (4)C23—C241.526 (4)
C6—N11.337 (4)C24—O221.250 (3)
C2—N211.324 (4)C24—O231.260 (3)
N3—C31.477 (3)
O21—Ca1—O21ii128.61 (11)O21—Ca1—O172.63 (12)
O23i—Ca1—O23iii77.97 (10)O21—Ca1—O285.89 (12)
O21—Ca1—O23i80.29 (7)O21—Ca1—O3110.60 (13)
O21—Ca1—O23iii147.44 (7)O23i—Ca1—O1119.34 (11)
O1—Ca1—O2113.79 (16)O23i—Ca1—O2117.14 (12)
O1—Ca1—O369.53 (15)O23i—Ca1—O371.28 (13)
O2—Ca1—O3163.04 (16)
N3—C2—N21—C21177.1 (2)C22—N22—C23—C24111.7 (3)
C2—N21—C21—C2280.8 (3)N22—C23—C24—O2221.3 (4)
N21—C21—C22—N220.5 (4)N22—C23—C24—O23160.1 (2)
C21—C22—N22—C23177.5 (3)
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z+1/2; (iii) x+1, y+1, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1AW···O22ii0.902.163.048 (5)168
O1—H1BW···O5iv0.882.322.962 (5)130
O2—H2AW···O22v0.871.822.667 (4)166
O2—H2BW···O5vi0.851.822.655 (5)164
O3—H3AW···O22iii0.891.822.692 (5)166
O3—H3BW···O22vii0.891.892.744 (5)162
N6—H6B···O50.881.942.598 (3)131
N6—H6A···O4vii0.881.972.761 (3)149
N21—H21···O23viii0.882.052.861 (3)152
N22—H22A···N5ix0.882.343.132 (3)150
Symmetry codes: (ii) x+1, y, z+1/2; (iii) x+1, y+1, z+1/2; (iv) x+1, y, z; (v) x+3/2, y+1/2, z+1/2; (vi) x, y, z+1/2; (vii) x1/2, y+1/2, z; (viii) x+1/2, y+1/2, z; (ix) x+3/2, y1/2, z.
 

Subscribe to Acta Crystallographica Section C: Structural Chemistry

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds