Aquadi-n-but­yl(5-methyl­pyrazine-2-carboxyl­ato)tin(IV) methanol solvate

In the monomeric title compound, [Sn(C₄H₉)₂(C₆H₅N₂O₂)₂(H₂O)]·CH₃OH, the Sn atom is seven-coordinate, displaying a distorted penta­gonal bipyramidal SnC₂N₂O₃ geometry with the two C atoms in the axial sites. In the crystal structure, inter­molecular O—H...O hydrogen bonds link the complex and solvent mol­ecules into infinite chains.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.036
• wR factor = 0.122
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.22 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.59 Ratio

Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C14
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Sn1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C15
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         10
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C13    -   C14    ...       1.39 Ang.
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C19    -   C20    ...       1.37 Ang.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.95
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C12

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         12

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

Self-assembled organotin derivatives of carboxylic acid ligands have been extensively studied due to their biological activities (Gielen et al., 1988). 2-Methylpyrazine-5-carboxylic acid is a good bridging ligand that can sometimes be used to generate unexpected and interesting coordination polymers, and small changes in experimental conditions can lead to very different architectures.

The title compound, (I), consists of two butyl, two N,O-bidentate 2-methylpyrazine-5-carboxylate groups and a water molecule bonded to the Sn atom and has a monomeric structure. The Sn atom is seven-coordinate with a distorted pentagonal bipyramidal SnC₂N₂O₃ geometry (Table 1, Fig. 1). Around the central Sn atom, atoms C13 and C17 of the two butyl groups occupy the axial position, while O and N atoms lie in equatorial positions. The sum of the angles between the tin atom and the equatorial atoms is 360.4°. The axial bond angle C17—Sn1—C13 [161.6 (3)°] deviates from linearity by over 18°, which shows that these atoms have significant deviations from ideal pentagonal bipyramidal geometry. Otherwise, the bond lenghts and angles in (I) are similar to those in related structures (Ma et al., 2004).

In the crystal, strong intermolecular O—H···O hydrogen bonds (Table 2) between O atoms of the carboxyl groups, methanol and coordinate water molecules result in the formation of one-dimensional polymeric chains (Fig. 2).

Related literature

For general background, see: Gielen et al. (1988). For a related structure, see: Ma et al. (2004).

S2. Experimental

A mixture of dibutyltin dichloride (1.0 mmol, 0.304 g), 2-methylpyrazine-5-carboxylic acid (2.0 mmol, 0.276 g) and sodium ethoxide (0.136 g, 2.0 mmol) in ethanol (with 5% water) (80 ml) was heated under reflux for 8 h at 303 K. The resulting clear solution was evaporated under vacuum and the product recrystallized from a mixture of methanol to yield colourless, blocks of (I). Yield 0.452 g, 78%, m.p. 438 K, analysis, calculated for C₂₁H₃₄N₄O₆Sn: C 45.26, H, 6.15; N 10.05%; found: C 45.39, H 6.29, N, 10.12%.

S3. Refinement

The H atoms were positioned geometrically (C—H = 0.93–0.97 Å, O—H = 0.82–0.85 Å) and refined as riding with U_iso(H) = 1.2U_eq(C/O) or 1.5U_eq(methyl C)

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures

	Fig. 1. The molecular structure of (I), with displacement ellipsoids for the non-hydrogen atoms drawn at the 30% probability level. The hydrogen bond is indicated by a double-dashed line.
	Fig. 2. Packing diagram of the crystal structure of (I), showing the one-dimensional chains that form along the c axis. H atoms are omitted for clarity and dashed lines link the donor and acceptor O atoms of the hydrogen bonds.

Aquadi-n-butyl(5-methylpyrazine-2-carboxylato)tin(IV) methanol solvate

Crystal data

[Sn(C4H9)2(C6H5N2O2)2(H2O)]·CH4O	F(000) = 2288
Mr = 557.21	Dx = 1.456 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4606 reflections
a = 20.609 (5) Å	θ = 2.4–25.3°
b = 17.119 (4) Å	µ = 1.05 mm^−1
c = 14.558 (3) Å	T = 298 K
β = 98.178 (3)°	Block, colourless
V = 5084 (2) Å^3	0.58 × 0.56 × 0.49 mm
Z = 8

Data collection

Bruker SMART CCD diffractometer	4462 independent reflections
Radiation source: fine-focus sealed tube	2981 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −15→24
Tmin = 0.582, Tmax = 0.628	k = −20→20
12959 measured reflections	l = −17→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H-atom parameters constrained
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0455P)^2 + 11.2132P] where P = (Fo^2 + 2Fc^2)/3
4462 reflections	(Δ/σ)max = 0.002
289 parameters	Δρmax = 0.58 e Å^−3
12 restraints	Δρmin = −0.67 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Sn1	0.256428 (17)	1.005653 (19)	0.41391 (2)	0.05022 (15)
N1	0.3679 (2)	0.9489 (2)	0.4509 (3)	0.0496 (10)
N2	0.4975 (2)	0.9001 (3)	0.4682 (4)	0.0746 (15)
N3	0.1453 (2)	1.0475 (3)	0.4696 (3)	0.0597 (12)
N4	0.0240 (3)	1.1105 (4)	0.4929 (4)	0.0858 (17)
O1	0.30863 (18)	1.0137 (2)	0.2956 (2)	0.0579 (9)
O2	0.4017 (2)	1.0160 (3)	0.2351 (3)	0.0784 (12)
O3	0.18771 (19)	1.0558 (2)	0.3031 (3)	0.0673 (11)
O4	0.09289 (19)	1.1052 (3)	0.2392 (3)	0.0757 (12)
O5	0.26009 (19)	0.9499 (2)	0.5931 (3)	0.0736 (11)
H1	0.2327	0.9135	0.5983	0.088*
H2	0.2730	0.9647	0.6484	0.088*
C1	0.3704 (3)	1.0012 (3)	0.2976 (4)	0.0529 (13)
C2	0.4039 (3)	0.9618 (3)	0.3833 (4)	0.0513 (13)
C3	0.4686 (3)	0.9380 (4)	0.3940 (4)	0.0679 (16)
H3	0.4932	0.9491	0.3467	0.082*
C4	0.4612 (3)	0.8866 (3)	0.5350 (4)	0.0620 (15)
C5	0.3965 (3)	0.9124 (3)	0.5273 (4)	0.0591 (14)
H5	0.3727	0.9042	0.5762	0.071*
C6	0.4918 (3)	0.8426 (4)	0.6191 (4)	0.090 (2)
H6A	0.5364	0.8300	0.6129	0.135*
H6B	0.4677	0.7953	0.6250	0.135*
H6C	0.4910	0.8743	0.6733	0.135*
C7	0.1295 (3)	1.0804 (3)	0.3063 (4)	0.0586 (14)
C8	0.1057 (3)	1.0790 (3)	0.3989 (4)	0.0532 (13)
C9	0.0454 (3)	1.1085 (4)	0.4106 (5)	0.0747 (18)
H9	0.0183	1.1279	0.3591	0.090*
C10	0.0627 (3)	1.0788 (4)	0.5628 (5)	0.0722 (17)
C11	0.1233 (3)	1.0474 (4)	0.5517 (4)	0.0729 (17)
H11	0.1492	1.0256	0.6027	0.087*
C12	0.0393 (4)	1.0786 (5)	0.6554 (5)	0.103 (3)
H12A	−0.0033	1.1022	0.6499	0.155*
H12B	0.0694	1.1076	0.6989	0.155*
H12C	0.0368	1.0258	0.6767	0.155*
C13	0.2915 (4)	1.1117 (4)	0.4756 (5)	0.091 (2)
H13A	0.3165	1.1364	0.4319	0.110*
H13B	0.2532	1.1442	0.4778	0.110*
C14	0.3295 (5)	1.1185 (4)	0.5624 (6)	0.128 (3)
H14A	0.3671	1.0843	0.5633	0.153*
H14B	0.3038	1.0990	0.6084	0.153*
C15	0.3547 (4)	1.1996 (4)	0.5931 (7)	0.111 (3)
H15A	0.3814	1.2197	0.5488	0.133*
H15B	0.3178	1.2346	0.5938	0.133*
C16	0.3937 (5)	1.1977 (5)	0.6860 (7)	0.139 (4)
H16A	0.4091	1.2494	0.7029	0.208*
H16B	0.4305	1.1634	0.6854	0.208*
H16C	0.3670	1.1792	0.7303	0.208*
C17	0.2167 (3)	0.8926 (3)	0.3962 (4)	0.0697 (17)
H17A	0.2404	0.8590	0.4431	0.084*
H17B	0.1716	0.8946	0.4079	0.084*
C18	0.2177 (4)	0.8561 (4)	0.3060 (5)	0.107 (3)
H18A	0.2627	0.8497	0.2950	0.129*
H18B	0.1955	0.8895	0.2577	0.129*
C19	0.1832 (6)	0.7749 (5)	0.3022 (7)	0.148 (4)
H19A	0.2050	0.7431	0.3525	0.178*
H19B	0.1384	0.7826	0.3133	0.178*
C20	0.1821 (7)	0.7340 (7)	0.2212 (9)	0.217 (7)
H20A	0.1597	0.6853	0.2258	0.326*
H20B	0.2262	0.7240	0.2103	0.326*
H20C	0.1596	0.7640	0.1707	0.326*
C21	0.1267 (4)	0.7823 (4)	0.5608 (5)	0.104 (3)
H21A	0.1147	0.7483	0.6081	0.156*
H21B	0.1551	0.7550	0.5249	0.156*
H21C	0.0879	0.7986	0.5210	0.156*
O6	0.1586 (3)	0.8466 (3)	0.6014 (4)	0.123 (2)
H6	0.1340	0.8703	0.6312	0.147*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.0454 (2)	0.0530 (2)	0.0517 (2)	0.00077 (18)	0.00511 (16)	−0.00375 (17)
N1	0.048 (2)	0.050 (2)	0.051 (3)	0.001 (2)	0.006 (2)	−0.002 (2)
N2	0.057 (3)	0.092 (4)	0.074 (3)	0.017 (3)	0.004 (3)	0.000 (3)
N3	0.055 (3)	0.062 (3)	0.062 (3)	0.010 (2)	0.010 (2)	0.000 (2)
N4	0.066 (3)	0.111 (5)	0.084 (4)	0.014 (3)	0.024 (3)	0.010 (3)
O1	0.046 (2)	0.077 (2)	0.050 (2)	0.0019 (19)	0.0050 (17)	0.0063 (18)
O2	0.065 (3)	0.114 (3)	0.059 (3)	0.007 (2)	0.018 (2)	0.018 (2)
O3	0.056 (2)	0.088 (3)	0.058 (2)	0.019 (2)	0.0097 (19)	0.005 (2)
O4	0.057 (2)	0.110 (3)	0.058 (3)	0.018 (2)	0.002 (2)	0.011 (2)
O5	0.072 (3)	0.078 (3)	0.069 (3)	−0.014 (2)	0.003 (2)	0.000 (2)
C1	0.053 (3)	0.058 (3)	0.047 (3)	0.001 (3)	0.007 (3)	−0.003 (3)
C2	0.049 (3)	0.056 (3)	0.049 (3)	0.004 (3)	0.006 (3)	−0.007 (2)
C3	0.061 (4)	0.083 (4)	0.061 (4)	0.012 (3)	0.012 (3)	−0.006 (3)
C4	0.061 (4)	0.058 (3)	0.063 (4)	0.009 (3)	−0.005 (3)	−0.001 (3)
C5	0.058 (4)	0.064 (3)	0.054 (3)	−0.002 (3)	0.002 (3)	−0.007 (3)
C6	0.087 (5)	0.103 (5)	0.077 (5)	0.022 (4)	0.000 (4)	0.009 (4)
C7	0.051 (3)	0.063 (3)	0.060 (4)	0.000 (3)	0.001 (3)	−0.004 (3)
C8	0.048 (3)	0.054 (3)	0.058 (3)	0.002 (3)	0.007 (3)	−0.004 (3)
C9	0.052 (4)	0.096 (5)	0.075 (4)	0.011 (3)	0.006 (3)	0.009 (4)
C10	0.072 (4)	0.076 (4)	0.073 (4)	0.006 (4)	0.024 (4)	0.002 (3)
C11	0.074 (4)	0.082 (4)	0.062 (4)	0.016 (4)	0.010 (3)	0.001 (3)
C12	0.101 (6)	0.129 (7)	0.090 (5)	0.021 (5)	0.048 (5)	0.011 (5)
C13	0.122 (6)	0.059 (4)	0.084 (5)	0.006 (4)	−0.020 (5)	−0.013 (3)
C14	0.136 (8)	0.087 (6)	0.148 (8)	−0.019 (5)	−0.023 (7)	−0.027 (5)
C15	0.102 (6)	0.070 (5)	0.157 (8)	−0.022 (4)	0.007 (6)	−0.034 (5)
C16	0.165 (10)	0.097 (6)	0.153 (9)	−0.007 (6)	0.016 (8)	−0.028 (6)
C17	0.071 (4)	0.053 (3)	0.083 (4)	−0.013 (3)	0.005 (3)	−0.003 (3)
C18	0.131 (7)	0.083 (5)	0.108 (6)	−0.028 (5)	0.021 (5)	−0.037 (4)
C19	0.191 (11)	0.111 (7)	0.142 (9)	−0.040 (7)	0.023 (8)	−0.055 (6)
C20	0.265 (17)	0.138 (10)	0.244 (16)	−0.054 (11)	0.022 (13)	−0.074 (11)
C21	0.115 (6)	0.093 (5)	0.107 (6)	−0.020 (5)	0.028 (5)	−0.019 (5)
O6	0.118 (4)	0.129 (4)	0.134 (4)	−0.045 (4)	0.065 (3)	−0.047 (3)

Geometric parameters (Å, º)

Sn1—C17	2.103 (5)	C10—C12	1.494 (9)
Sn1—C13	2.107 (6)	C11—H11	0.9300
Sn1—O1	2.161 (4)	C12—H12A	0.9600
Sn1—O3	2.167 (4)	C12—H12B	0.9600
Sn1—N1	2.481 (4)	C12—H12C	0.9600
Sn1—N3	2.635 (5)	C13—C14	1.392 (9)
Sn1—O5	2.770 (4)	C13—H13A	0.9700
N1—C2	1.331 (6)	C13—H13B	0.9700
N1—C5	1.337 (6)	C14—C15	1.526 (8)
N2—C3	1.326 (7)	C14—H14A	0.9700
N2—C4	1.330 (8)	C14—H14B	0.9700
N3—C8	1.333 (6)	C15—C16	1.473 (10)
N3—C11	1.337 (7)	C15—H15A	0.9700
N4—C10	1.317 (8)	C15—H15B	0.9700
N4—C9	1.334 (8)	C16—H16A	0.9600
O1—C1	1.288 (6)	C16—H16B	0.9600
O2—C1	1.215 (7)	C16—H16C	0.9600
O3—C7	1.278 (6)	C17—C18	1.456 (8)
O4—C7	1.223 (6)	C17—H17A	0.9700
O5—H2	0.8500	C17—H17B	0.9700
O5—H1	0.8500	C18—C19	1.558 (9)
C1—C2	1.498 (7)	C18—H18A	0.9700
C2—C3	1.383 (7)	C18—H18B	0.9700
C3—H3	0.9300	C19—C20	1.369 (11)
C4—C5	1.395 (8)	C19—H19A	0.9700
C4—C6	1.498 (8)	C19—H19B	0.9700
C5—H5	0.9300	C20—H20A	0.9600
C6—H6A	0.9600	C20—H20B	0.9600
C6—H6B	0.9600	C20—H20C	0.9600
C6—H6C	0.9600	C21—O6	1.372 (8)
C7—C8	1.498 (8)	C21—H21A	0.9600
C8—C9	1.376 (8)	C21—H21B	0.9600
C9—H9	0.9300	C21—H21C	0.9600
C10—C11	1.390 (8)	O6—H6	0.8200
C17—Sn1—C13	161.7 (3)	N4—C10—C12	117.4 (6)
C17—Sn1—O1	100.9 (2)	C11—C10—C12	121.0 (6)
C13—Sn1—O1	96.1 (2)	N3—C11—C10	121.9 (6)
C17—Sn1—O3	94.1 (2)	N3—C11—H11	119.0
C13—Sn1—O3	97.1 (2)	C10—C11—H11	119.0
O1—Sn1—O3	74.24 (14)	C10—C12—H12A	109.5
C17—Sn1—N1	89.9 (2)	C10—C12—H12B	109.5
C13—Sn1—N1	89.6 (2)	H12A—C12—H12B	109.5
O1—Sn1—N1	69.34 (14)	C10—C12—H12C	109.5
O3—Sn1—N1	143.46 (14)	H12A—C12—H12C	109.5
C17—Sn1—N3	87.0 (2)	H12B—C12—H12C	109.5
C13—Sn1—N3	84.0 (2)	C14—C13—Sn1	125.0 (5)
O1—Sn1—N3	141.33 (14)	C14—C13—H13A	106.1
O3—Sn1—N3	67.44 (15)	Sn1—C13—H13A	106.1
N1—Sn1—N3	149.10 (14)	C14—C13—H13B	106.1
C17—Sn1—O5	75.89 (18)	Sn1—C13—H13B	106.1
C13—Sn1—O5	86.2 (2)	H13A—C13—H13B	106.3
O1—Sn1—O5	145.38 (13)	C13—C14—C15	117.7 (7)
O3—Sn1—O5	139.93 (13)	C13—C14—H14A	107.9
N1—Sn1—O5	76.15 (13)	C15—C14—H14A	107.9
N3—Sn1—O5	73.29 (13)	C13—C14—H14B	107.9
C2—N1—C5	117.8 (5)	C15—C14—H14B	107.9
C2—N1—Sn1	111.8 (3)	H14A—C14—H14B	107.2
C5—N1—Sn1	130.4 (4)	C16—C15—C14	111.6 (7)
C3—N2—C4	116.5 (5)	C16—C15—H15A	109.3
C8—N3—C11	116.3 (5)	C14—C15—H15A	109.3
C8—N3—Sn1	109.6 (3)	C16—C15—H15B	109.3
C11—N3—Sn1	134.0 (4)	C14—C15—H15B	109.3
C10—N4—C9	116.3 (6)	H15A—C15—H15B	108.0
C1—O1—Sn1	125.1 (3)	C15—C16—H16A	109.5
C7—O3—Sn1	128.4 (4)	C15—C16—H16B	109.5
H2—O5—Sn1	138.8	H16A—C16—H16B	109.5
Sn1—O5—H1	113.9	C15—C16—H16C	109.5
Sn1—O5—H2	138.8	H16A—C16—H16C	109.5
H1—O5—H2	105.0	H16B—C16—H16C	109.5
O2—C1—O1	125.3 (5)	C18—C17—Sn1	116.8 (4)
O2—C1—C2	119.2 (5)	C18—C17—H17A	108.1
O1—C1—C2	115.5 (5)	Sn1—C17—H17A	108.1
N1—C2—C3	119.9 (5)	C18—C17—H17B	108.1
N1—C2—C1	116.8 (5)	Sn1—C17—H17B	108.1
C3—C2—C1	123.3 (5)	H17A—C17—H17B	107.3
N2—C3—C2	123.4 (6)	C17—C18—C19	110.5 (6)
N2—C3—H3	118.3	C17—C18—H18A	109.6
C2—C3—H3	118.3	C19—C18—H18A	109.6
N2—C4—C5	121.1 (5)	C17—C18—H18B	109.6
N2—C4—C6	118.0 (5)	C19—C18—H18B	109.6
C5—C4—C6	120.9 (6)	H18A—C18—H18B	108.1
N1—C5—C4	121.2 (6)	C20—C19—C18	116.0 (9)
N1—C5—H5	119.4	C20—C19—H19A	108.3
C4—C5—H5	119.4	C18—C19—H19A	108.3
C4—C6—H6A	109.5	C20—C19—H19B	108.3
C4—C6—H6B	109.5	C18—C19—H19B	108.3
H6A—C6—H6B	109.5	H19A—C19—H19B	107.4
C4—C6—H6C	109.5	C19—C20—H20A	109.5
H6A—C6—H6C	109.5	C19—C20—H20B	109.5
H6B—C6—H6C	109.5	H20A—C20—H20B	109.5
O4—C7—O3	124.2 (6)	C19—C20—H20C	109.5
O4—C7—C8	118.7 (5)	H20A—C20—H20C	109.5
O3—C7—C8	117.2 (5)	H20B—C20—H20C	109.5
N3—C8—C9	121.1 (5)	O6—C21—H21A	109.5
N3—C8—C7	117.3 (5)	O6—C21—H21B	109.5
C9—C8—C7	121.6 (5)	H21A—C21—H21B	109.5
N4—C9—C8	122.8 (6)	O6—C21—H21C	109.5
N4—C9—H9	118.6	H21A—C21—H21C	109.5
C8—C9—H9	118.6	H21B—C21—H21C	109.5
N4—C10—C11	121.6 (6)	C21—O6—H6	109.3

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1···O6	0.85	1.92	2.755 (6)	169
O5—H2···O1^i	0.85	2.19	3.039 (5)	172
O6—H6···O4^i	0.82	1.93	2.703 (6)	156

Symmetry code: (i) x, −y+2, z+1/2.