Download citation
Download citation
link to html
In the title compound, C21H25N3O, the six-membered ring that is fused to two other six-membered rings in the estrane moiety adopts an envelope conformation. The compound shows intermolecular hydrogen bonding of the amine group to an N atom of the pyrimidine moiety, as well as weak intermolecular interactions involving H atoms in the hydro­phobic residue of the mol­ecule.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270104012326/ga1051sup1.cif
Contains datablocks General, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270104012326/ga1051Isup2.hkl
Contains datablock I

CCDC reference: 245890

Comment top

Over the years, several steroidal derivatives with an additional ring (E) fused at either the C2,3 or the C16,17 positions have been prepared (Siddiqui et al., 1995; Camoutsis, 1996; Singh & Singh, 1999). These compounds exhibit a variety of biological properties, such as steroidal receptor antagonistic activity and/or antiinflammatory activity. The title compound, (I), was synthesized in order to study the influence of ring annelation of aminopyrimidine to the oestrane framework on the binding affinity to the oestrogen receptor (ERα). Furthermore, a number of tripeptides have been linked to the amine group as potential ligands for 99m-technetium or 186-rhenium and 188-rhenium radionuclides (Matsumoto et al., 2003). These compounds are to be assayed as potential radiodiagnostics, e.g. for minimal oestrogen positive breast cancer. \sch

In order to investigate the conformation of (I) as the steroid component of these oestrane-tripeptide hybrids, an X-ray structural analysis was carried out. There is one independent molecule per asymmetric unit (Fig. 1). Ring A shows little distortion from planarity, as is evident in other oestrones and oestradiols for which X-ray crystal structural analyses have been carried out. Ring C, with trans fusion to rings B and D, has a chair conformation. As a cyclohexene, ring B in oestranes is usually conformationally more flexible (Bucourt & Hainault, 1967; Yamamoto et al., 2004). In (I), ring B has an envelope conformation, as characterized by the Cremer & Pople (1975) puckering parameters Q = 0.533 (2) Å, θ = 52.0 (3)° and ϕ = 172.1 (3)° [for a perfect envelope conformation, θ = 54.7° and ϕ = k × 60°; for a perfect half-chair conformation (the next closest conformation), θ = 50.8° and ϕ = k × 60° + 30° (Boeyens, 1978)]. This configuration is also in accordance with the relative signs of the endocyclic torsion angles within ring B (see Boeyens, 1978).

Ring D has an envelope conformation [Q = 0.378 (2) Å and ϕ = 211.0 (3)°], with atom C14 as the flap, a pseudorotation angle Δ = 12.8 (2)° and a maximum torsion angle ϕm = 38.2 (1)° (Rao et al., 1981) for the atom sequence C13—C17. The aminopyrimidine ring shows a minor distortion from planarity [C16—C19—N1···N3 torsion angle 4.7 (4)°], which may be due to the hydrogen bonding involving both atom N1 and one of the H atoms on N3 (see below). While the C19—N1 [1.335 (3) Å] and C17—N2 [1.326 (3) Å] bond distances, as well as the N1—C20 [1.350 (3) Å] and N2—C20 [1.358 (3) Å] bond distances, are similar to one another and to the corresponding bond lengths found in the parent compound 2-aminopyrimidine (Furberg et al., 1979), the C16—C17 bond length [1.404 (3) Å] is longer than both the corresponding bond length in 2-aminopyrimidine (Furberg et al., 1979) and the corresponding typical bond lengths found in 16,17-unsaturated steroids, e.g., in 5α-androst-16-en-3-one (1.302 Å; Cox & Turner, 1984) and in 17-(3-oxazolin-4-yl)androsta-4,16-dien-3-one (1.342 Å; Meetsma et al., 1993). These differences may be rationalized by taking into account that a hydrogen bond to N1 as donor favours the iminodiazacyclohexadiene ring having a single bond at C16—C17 over other resonance forms for the aminopyrimidine unit.

In the crystal structure (Fig. 2), molecules of (I) pack in chains of two rows of molecules, where parallel chains are arranged in a stepwise fashion. Another arrangement of parallel chains, tilted by 81.02 (7)°, is also ordered in a stepwise fashion. The governing factor is the hydrogen bond formed by the amine group of the aminopyrimidine moiety with one of the pyrimidine N atoms of a neighbouring molecule. It is clear from the X-ray data that only one H atom of the amine group bound to atom C20 forms a strong hydrogen bond with one adjacent atom, N1 (Table 1). The N3—H25···N2ii interaction is weaker, with an H25···N2 distance of 2.48 Å (Table 1).

From an AM1 calculation of the pyrimidine fragment of I1), it is evident that the electrostatic potential at atom N1 (−0.310) is higher than that at the other N atoms, especially at atom N2 (−0.273 for N2 and −0.235 for the NH2 N atom). This result strongly suggests that any protic interaction will take place predominantely at atom N1. This fact is not only important in evaluating the crystal structure of (I), but can also be used to argue the possible conformations of (I)-tripeptide hybrids.

The arrangement of molecules of (I) in the crystal forces neighbouring molecules on the same side of the chain to lie close together, as shown by the intermolecular contacts (Table 1).

Experimental top

Compound (I) was prepared by condensation of 3-methoxy-16-(N-methyl-N-phenylaminomethylidene)oestra-1,3,5(10)-trien-17-one with guanidine hydrochoride (Matsumoto et al., 2003). The crystal used for the X-ray structure analysis was obtained by recrystallization of (I) from dichloromethane-ether-hexane(1:1:1). Analysis, found: C 75.13, H 7.48, N 12.45%; calculated for C21H25N3O: C 75.19, H 7.51, N 12.53%,

Refinement top

All H atoms were refined as riding on their parent atoms, with Uiso(H) values set at 1.2Ueq of the parent O and C atoms. The final difference-map peak is 1.69 Å from atom H3. The absolute configuration could not be determined from the X-ray data but was known from the synthetic route.

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: CrystalStructure.

Figures top
[Figure 1] Fig. 1. A view of the molecule of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. The unit cell of (I), viewed down the a axis.
2'-Amino-3-methoxypyrimidino[5',4':16,17]oestra-1,3,5(10),16-tetraene top
Crystal data top
C21H25N3OF(000) = 720.00
Mr = 335.45Dx = 1.290 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2ac 2abCell parameters from 4940 reflections
a = 8.198 (2) Åθ = 3.1–27.5°
b = 9.303 (2) ŵ = 0.08 mm1
c = 22.644 (5) ÅT = 123 K
V = 1727.0 (6) Å3Prism, colourless
Z = 40.12 × 0.10 × 0.08 mm
Data collection top
Rigaku Saturn
diffractometer
2690 reflections with F2 > 2σ(F2)
Detector resolution: 7.31 pixels mm-1Rint = 0.038
ω scansθmax = 27.5°
Absorption correction: multi-scan
(Jacobson, 1998)
h = 108
Tmin = 0.919, Tmax = 0.994k = 1110
14004 measured reflectionsl = 2929
3850 independent reflections
Refinement top
Refinement on F2 w = 1/[0.0007Fo2 + 0.5σ(Fo2)]/(4Fo2)
R[F2 > 2σ(F2)] = 0.041(Δ/σ)max < 0.001
wR(F2) = 0.112Δρmax = 0.64 e Å3
S = 1.01Δρmin = 0.58 e Å3
3850 reflectionsExtinction correction: Larson (1970)
253 parametersExtinction coefficient: 107.2 (39)
H-atom parameters constrained
Crystal data top
C21H25N3OV = 1727.0 (6) Å3
Mr = 335.45Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.198 (2) ŵ = 0.08 mm1
b = 9.303 (2) ÅT = 123 K
c = 22.644 (5) Å0.12 × 0.10 × 0.08 mm
Data collection top
Rigaku Saturn
diffractometer
3850 independent reflections
Absorption correction: multi-scan
(Jacobson, 1998)
2690 reflections with F2 > 2σ(F2)
Tmin = 0.919, Tmax = 0.994Rint = 0.038
14004 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.041253 parameters
wR(F2) = 0.112H-atom parameters constrained
S = 1.01Δρmax = 0.64 e Å3
3850 reflectionsΔρmin = 0.58 e Å3
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 using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.0736 (2)0.3739 (2)0.22700 (7)0.0297 (4)
N10.9514 (2)0.6197 (2)0.04325 (8)0.0234 (5)
N20.6604 (2)0.5812 (2)0.03685 (8)0.0213 (4)
N30.7855 (2)0.7799 (2)0.00536 (8)0.0275 (5)
C10.1463 (3)0.0712 (2)0.12471 (9)0.0221 (5)
C20.0607 (3)0.1765 (2)0.15485 (9)0.0231 (6)
C30.1427 (3)0.2638 (2)0.19481 (9)0.0227 (5)
C40.3084 (3)0.2449 (2)0.20293 (9)0.0226 (5)
C50.3946 (3)0.1393 (2)0.17243 (9)0.0221 (5)
C60.5757 (3)0.1293 (2)0.18440 (10)0.0284 (6)
C70.6647 (3)0.0218 (2)0.14596 (10)0.0262 (6)
C80.5599 (3)0.1102 (2)0.13504 (9)0.0206 (5)
C90.4081 (2)0.0666 (2)0.09916 (9)0.0194 (5)
C100.3136 (3)0.0485 (2)0.13279 (9)0.0204 (5)
C110.3055 (3)0.1972 (2)0.08000 (9)0.0217 (5)
C120.4070 (3)0.3193 (2)0.05066 (9)0.0222 (5)
C130.5497 (2)0.3615 (2)0.09065 (9)0.0197 (5)
C140.6523 (2)0.2252 (2)0.10146 (9)0.0206 (5)
C150.8181 (3)0.2789 (2)0.12501 (10)0.0254 (6)
C160.8339 (3)0.4160 (2)0.08978 (9)0.0223 (5)
C170.6823 (3)0.4618 (2)0.06789 (9)0.0196 (5)
C180.4865 (3)0.4335 (2)0.14756 (10)0.0274 (6)
C190.9657 (3)0.5009 (2)0.07590 (10)0.0248 (6)
C200.7994 (3)0.6558 (2)0.02564 (9)0.0209 (5)
C210.0993 (3)0.3773 (3)0.23098 (11)0.0339 (7)
H10.08930.01200.09750.026*
H20.05290.18880.14840.027*
H30.36470.30500.23000.027*
H40.59060.10260.22450.034*
H50.62240.22140.17790.035*
H60.76240.00680.16530.031*
H70.69070.06540.10920.032*
H80.52570.14840.17190.024*
H90.44680.02260.06400.023*
H100.22560.16570.05250.026*
H110.25290.23540.11400.026*
H120.44820.28640.01390.027*
H130.33930.40080.04440.027*
H140.67360.18580.06350.024*
H150.81490.29720.16630.030*
H160.90390.21340.11660.031*
H170.47910.53430.14150.034*
H180.56000.41450.17900.034*
H190.38180.39650.15720.034*
H201.07040.47420.09010.029*
H210.13330.32360.26450.042*
H220.13530.47390.23480.042*
H230.14500.33630.19630.042*
H240.67130.79300.01940.033*
H250.88330.82090.01940.033*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0210 (8)0.0271 (8)0.0410 (9)0.0004 (7)0.0008 (7)0.0123 (7)
N10.0194 (9)0.0249 (9)0.0258 (9)0.0002 (8)0.0001 (8)0.0022 (8)
N20.0188 (9)0.0223 (9)0.0228 (9)0.0014 (7)0.0001 (7)0.0003 (7)
N30.0204 (9)0.0266 (9)0.0354 (10)0.0031 (8)0.0006 (8)0.0073 (8)
C10.0209 (11)0.0205 (10)0.0247 (11)0.0036 (9)0.0050 (9)0.0012 (8)
C20.0173 (11)0.0220 (10)0.0299 (12)0.0008 (9)0.0027 (9)0.0028 (9)
C30.0245 (11)0.0190 (10)0.0247 (11)0.0004 (9)0.0017 (9)0.0017 (8)
C40.0222 (12)0.0203 (11)0.0255 (11)0.0026 (9)0.0020 (9)0.0022 (8)
C50.0196 (11)0.0240 (10)0.0227 (11)0.0019 (9)0.0009 (8)0.0006 (9)
C60.0193 (11)0.0286 (11)0.0374 (13)0.0016 (10)0.0047 (10)0.0100 (10)
C70.0183 (11)0.0272 (11)0.0331 (12)0.0023 (9)0.0007 (10)0.0032 (10)
C80.0178 (10)0.0214 (10)0.0225 (10)0.0002 (8)0.0009 (8)0.0001 (8)
C90.0168 (10)0.0211 (10)0.0202 (10)0.0002 (9)0.0022 (8)0.0002 (8)
C100.0214 (11)0.0183 (10)0.0214 (10)0.0023 (9)0.0013 (9)0.0026 (8)
C110.0160 (11)0.0221 (11)0.0270 (11)0.0015 (9)0.0043 (9)0.0035 (9)
C120.0184 (10)0.0223 (10)0.0260 (11)0.0001 (9)0.0019 (9)0.0025 (9)
C130.0159 (10)0.0195 (10)0.0238 (11)0.0000 (9)0.0003 (8)0.0002 (8)
C140.0159 (10)0.0233 (10)0.0227 (10)0.0004 (9)0.0017 (8)0.0007 (8)
C150.0175 (11)0.0269 (11)0.0318 (12)0.0005 (10)0.0040 (9)0.0052 (9)
C160.0210 (11)0.0237 (11)0.0223 (10)0.0001 (9)0.0014 (9)0.0004 (8)
C170.0170 (10)0.0204 (10)0.0215 (10)0.0002 (9)0.0014 (9)0.0027 (8)
C180.0235 (11)0.0263 (11)0.0325 (12)0.0008 (9)0.0003 (10)0.0037 (10)
C190.0160 (11)0.0286 (11)0.0298 (12)0.0005 (9)0.0012 (9)0.0005 (9)
C200.0205 (11)0.0194 (10)0.0228 (10)0.0005 (9)0.0007 (9)0.0024 (8)
C210.0236 (12)0.0378 (13)0.040 (1)0.0031 (11)0.0016 (11)0.0072 (11)
Geometric parameters (Å, º) top
O1—C31.379 (2)C16—C171.404 (3)
O1—C211.421 (3)C16—C191.374 (3)
N1—C191.335 (3)N3—H240.9957
N1—C201.350 (3)N3—H250.9436
N2—C171.326 (3)C1—H10.9499
N2—C201.358 (3)C2—H20.9500
N3—C201.356 (3)C4—H30.9500
C1—C21.385 (3)C6—H40.9499
C1—C101.400 (3)C6—H50.9500
C2—C31.390 (3)C7—H60.9500
C3—C41.381 (3)C7—H70.9500
C4—C51.394 (3)C8—H80.9500
C5—C61.512 (3)C9—H90.9500
C5—C101.400 (3)C11—H100.9500
C6—C71.513 (3)C11—H110.9501
C7—C81.519 (3)C12—H120.9499
C8—C91.540 (3)C12—H130.9500
C8—C141.515 (3)C14—H140.9501
C9—C101.525 (3)C15—H150.9499
C9—C111.540 (3)C15—H160.9500
C11—C121.557 (3)C18—H170.9500
C12—C131.531 (3)C18—H180.9500
C13—C141.541 (3)C18—H190.9500
C13—C171.523 (3)C19—H200.9500
C13—C181.542 (3)C21—H210.9499
C14—C151.544 (3)C21—H220.9500
C15—C161.510 (3)C21—H230.9499
O1—C3—C2125.4 (2)H25—N3—H24129.9485
O1—C3—C4115.4 (2)C1—C2—H2120.4231
C21—O1—C3117.4 (2)H1—C1—C2118.7730
N2—C17—C13126.6 (2)H1—C1—C10118.6300
N2—C17—C16124.1 (2)H2—C2—C3120.2725
C20—N2—C17114.4 (2)C3—C4—H3119.2854
N2—C20—N1126.3 (2)H3—C4—C5119.2198
N2—C20—N3117.4 (2)C5—C6—H4108.2917
N1—C19—C16122.2 (2)C5—C6—H5108.1867
C20—N1—C19116.8 (2)H4—C6—C7108.3790
N1—C20—N3116.2 (2)H5—C6—C7108.1847
C1—C2—C3119.3 (2)C6—C7—H6109.0701
C10—C1—C2122.6 (2)C6—C7—H7109.2664
C1—C10—C5117.2 (2)H5—C6—H4109.4631
C1—C10—C9122.6 (2)H6—C7—C8108.9874
C2—C3—C4119.2 (2)H7—C7—C8109.2436
C3—C4—C5121.5 (2)C7—C8—H8109.0585
C4—C5—C10120.2 (2)H7—C7—H6109.4672
C4—C5—C6116.9 (2)C8—C9—H9106.6153
C10—C5—C6122.9 (2)H8—C8—C9108.8839
C5—C6—C7114.3 (2)H8—C8—C14108.9288
C5—C10—C9120.2 (2)C8—C14—H14105.8929
C6—C7—C8110.8 (2)H9—C9—C10106.6012
C7—C8—C9109.3 (2)H9—C9—C11106.6114
C7—C8—C14111.7 (2)C9—C11—H10108.5447
C8—C9—C10109.4 (2)C9—C11—H11108.3389
C8—C9—C11112.5 (2)C11—C12—H12109.2523
C14—C8—C9109.0 (2)C11—C12—H13109.5181
C8—C14—C13112.8 (2)H10—C11—C12108.2864
C8—C14—C15119.7 (2)H11—C11—C12108.3491
C11—C9—C10114.6 (2)H11—C11—H10109.4626
C9—C11—C12113.8 (2)H12—C12—C13109.2209
C11—C12—C13110.1 (2)H13—C12—C13109.3073
C12—C13—C17120.2 (2)H13—C12—H12109.4591
C12—C13—C18110.4 (2)C13—C14—H14105.8954
C12—C13—C14107.5 (2)C13—C18—H17109.2299
C17—C13—C1499.7 (2)C13—C18—H18109.4164
C18—C13—C14114.1 (2)C13—C18—H19109.7766
C13—C14—C15105.6 (2)H14—C14—C15105.9498
C13—C17—C16109.0 (2)C14—C15—H15111.9072
C18—C13—C17104.8 (2)C14—C15—H16111.9685
C14—C15—C1699.6 (2)H15—C15—C16111.7858
C15—C16—C17111.6 (2)H16—C15—C16111.8937
C15—C16—C19132.3 (2)H16—C15—H15109.4574
C19—C16—C17116.1 (2)C16—C19—H20118.8644
O1—C21—H21109.3545H18—C18—H17109.4726
O1—C21—H22109.6639H19—C18—H17109.4680
O1—C21—H23109.3960H19—C18—H18109.4633
N1—C19—H20118.9273H22—C21—H21109.4703
H24—N3—C20110.3702H23—C21—H21109.4644
H25—N3—C20116.5734H23—C21—H22109.4780
C21—O1—C3—C216.1 (3)C9—C8—C14—C15174.7 (2)
C21—O1—C3—C4165.9 (2)C8—C9—C10—C1155.2 (2)
C20—N1—C19—C161.9 (3)C8—C9—C10—C526.6 (2)
C19—N1—C20—N21.5 (3)C11—C9—C10—C127.8 (3)
C19—N1—C20—N3177.3 (2)C11—C9—C10—C5154.0 (2)
C20—N2—C17—C13175.7 (2)C8—C9—C11—C1249.2 (2)
C20—N2—C17—C162.2 (3)C10—C9—C11—C12174.9 (2)
C17—N2—C20—N10.4 (3)C9—C11—C12—C1352.7 (2)
C17—N2—C20—N3179.3 (2)C11—C12—C13—C1457.6 (2)
C10—C1—C2—C30.0 (3)C11—C12—C13—C17170.5 (2)
C2—C1—C10—C51.1 (3)C11—C12—C13—C1867.4 (2)
C2—C1—C10—C9179.4 (2)C12—C13—C14—C864.2 (2)
C1—C2—C3—O1178.9 (2)C12—C13—C14—C15163.3 (2)
C1—C2—C3—C40.9 (3)C17—C13—C14—C8169.8 (2)
O1—C3—C4—C5178.9 (2)C17—C13—C14—C1537.2 (2)
C2—C3—C4—C50.7 (3)C18—C13—C14—C858.6 (2)
C3—C4—C5—C6179.4 (2)C18—C13—C14—C1573.9 (2)
C3—C4—C5—C100.5 (3)C12—C13—C17—N243.7 (3)
C4—C5—C6—C7174.8 (2)C12—C13—C17—C16142.0 (2)
C10—C5—C6—C75.2 (3)C14—C13—C17—N2160.5 (2)
C4—C5—C10—C11.4 (3)C14—C13—C17—C1625.1 (2)
C4—C5—C10—C9179.7 (2)C18—C13—C17—N281.2 (2)
C6—C5—C10—C1178.6 (2)C18—C13—C17—C1693.2 (2)
C6—C5—C10—C90.2 (3)C8—C14—C15—C16163.6 (2)
C5—C6—C7—C837.0 (2)C13—C14—C15—C1635.1 (2)
C6—C7—C8—C964.7 (2)C14—C15—C16—C1719.6 (2)
C6—C7—C8—C14174.7 (2)C14—C15—C16—C19160.5 (2)
C7—C8—C9—C1058.1 (2)C15—C16—C17—N2178.1 (2)
C7—C8—C9—C11173.3 (2)C15—C16—C17—C133.6 (2)
C14—C8—C9—C10179.6 (2)C19—C16—C17—N21.9 (3)
C14—C8—C9—C1151.1 (2)C19—C16—C17—C13176.4 (2)
C7—C8—C14—C13179.0 (2)C15—C16—C19—N1179.7 (2)
C7—C8—C14—C1553.9 (2)C17—C16—C19—N10.3 (3)
C9—C8—C14—C1360.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H24···N1i1.002.053.019 (3)164
N3—H25···N2ii0.942.483.409 (3)169
Symmetry codes: (i) x1/2, y+3/2, z; (ii) x+1/2, y+3/2, z.

Experimental details

Crystal data
Chemical formulaC21H25N3O
Mr335.45
Crystal system, space groupOrthorhombic, P212121
Temperature (K)123
a, b, c (Å)8.198 (2), 9.303 (2), 22.644 (5)
V3)1727.0 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.12 × 0.10 × 0.08
Data collection
DiffractometerRigaku Saturn
diffractometer
Absorption correctionMulti-scan
(Jacobson, 1998)
Tmin, Tmax0.919, 0.994
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections
14004, 3850, 2690
Rint0.038
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.112, 1.01
No. of reflections3850
No. of parameters253
No. of restraints?
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.64, 0.58

Computer programs: CrystalClear (Rigaku, 1999), CrystalClear, CrystalStructure (Rigaku/MSC, 2004), SIR97 (Altomare et al., 1999), CRYSTALS (Watkin et al., 1996), PLATON (Spek, 2003), CrystalStructure.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H24···N1i1.002.053.019 (3)164
N3—H25···N2ii0.942.483.409 (3)169
Symmetry codes: (i) x1/2, y+3/2, z; (ii) x+1/2, y+3/2, z.
 

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