l-Valine l-valinium perchlorate monohydrate

Pandiarajan, S.; Sridhar, B.; Rajaram, R.K.

doi:10.1107/S160053680100681X

L-Valine L-valinium perchlorate monohydrate

S. Pandiarajan, B. Sridhar and R. K. Rajaram

In the title compound, C₅H₁₂NO₂⁺·ClO₄⁻·C₅H₁₁NO₂·H₂O, the valine as a zwitterion and valinium are bonded through a strong O—H

O hydrogen bond. Their ammonium groups and the perchlorate ion are held together by hydrogen bonds. Both valine and valinium show gauche-II forms.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680100681X/ob6036sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680100681X/ob6036Isup2.hkl Contains datablock I

CCDC reference: 165673

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
Disorder in solvent or counterion
R factor = 0.037
wR factor = 0.110
Data-to-parameter ratio = 7.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_302  Alert C Anion/Solvent Disorder .......................       8.00 Perc.

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           24.98
         From the CIF: _reflns_number_total               1665
         Count of symmetry unique reflns         1668
         Completeness (_total/calc)             99.82%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present          yes
          WARNING: Large fraction of Friedel related reflns may
                   be needed to determine absolute structure


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

Comment top

Valine is an essential amino acid. The crystal structures of L-valine (Torri et al., 1970), DL-valine (Mallikarjunan & Rao, 1969), L-valine hydrochloride monohydrate (Rao, 1969), L-valine hydrochloride (Parathasarathy, 1966; Ando et al., 1967), DL-valine hydrochloride (Di Blasio et al., 1977) and L-valine nitrate (Srinivasan & Rajaram, 1997) have been reported. In the present study, (I), the structure of valine with perchloric acid was undertaken.

All three possible rotational isomers of the valine molecule, viz. trans, gauche-I, gauche-II have been found in the crystalline state (Torri & Iitaka, 1970). In (I), both valine and valinium molecules are in gauche-II form. The amino N atom deviates from the carboxyl plane by 0.050 (6) Å in the valine molecule and 0.024 (7) Å in the valinium molecule, which corresponds to the twisting of the C—N bond out of the plane of the carboxyl group by 3.5 (4)° in valine and -1.8 (5)° in the valinium molecule. This tendency of twisting of the C—N bonds are found in various amino acids (Lakshminarayanan et al., 1967).

The valine and valinium molecules are bonded through a strong O—H···O hydrogen bond [O2B···O1B distance 2.562 (4) Å]. The perchlorate ion plays a vital role in forming hydrogen bonds with valine and valinium molecules, and stabilizing the structure. The water molecule links the ammonium group of the valinium molecule with perchlorate. A bifurcated hydrogen bond is observed in the case of the water molecule with perchlorate O atoms (Jeffrey & Saenger, 1991). The valine molecule is engaged in a head-to-tail straight (S2) sequence since the N11—H11A···O1B(x, y + 1, z) hydrogen bond connects two amino acids separated by a unit cell along the b axis, and a zigzag (Z1) sequence since N11—H11C···O2A(1 - x, y + 1/2, 1 - z) connects two 2₁-related amino acids (Vijayan, 1988).

Experimental top

Colorless needle-shaped crystals of (I) were obtained by the slow evaporation of an aqueous solution of L-valine and perchloric acid in a stoichiometric ratio of 2:1.

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. The molecular structure of (I) with the atom-numbering scheme and 50% probability displacement ellipsoids (Johnson, 1976).

L-Valine L-Valinium Perchlorate monohydrate top

Crystal data top

C₅H₁₁NO₂⁺·ClO₄⁻·C₅H₁₂NO₂·H₂O	F(000) = 376
M_r = 352.77	D_x = 1.366 Mg m⁻³ D_m = 1.369 Mg m⁻³ D_m measured by flotation in a mixture of carbon tetrachloride and xylene
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 11.235 (3) Å	Cell parameters from 25 reflections
b = 5.8312 (14) Å	θ = 8.1–13.7°
c = 13.0948 (19) Å	µ = 0.27 mm⁻¹
β = 91.282 (16)°	T = 293 K
V = 857.7 (3) Å³	Needles, colorless
Z = 2	0.25 × 0.23 × 0.13 mm

Data collection top

Enraf-Nonius sealed tube diffractometer	R_int = 0.011
Radiation source: fine-focus sealed tube	θ_max = 25.0°, θ_min = 2.4°
Graphite monochromator	h = 0→13
ω–2θ scans	k = 0→6
1751 measured reflections	l = −15→15
1665 independent reflections	3 standard reflections every 60 min
1481 reflections with I > 2σ(I)	intensity decay: none

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.037	w = 1/[σ²(F_o²) + (0.0658P)² + 0.132P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.110	(Δ/σ)_max = 0.002
S = 1.17	Δρ_max = 0.21 e Å⁻³
1665 reflections	Δρ_min = −0.26 e Å⁻³
228 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.030 (6)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.06 (11)

Crystal data top

C₅H₁₁NO₂⁺·ClO₄⁻·C₅H₁₂NO₂·H₂O	V = 857.7 (3) Å³
M_r = 352.77	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 11.235 (3) Å	µ = 0.27 mm⁻¹
b = 5.8312 (14) Å	T = 293 K
c = 13.0948 (19) Å	0.25 × 0.23 × 0.13 mm
β = 91.282 (16)°

Data collection top

Enraf-Nonius sealed tube diffractometer	R_int = 0.011
1751 measured reflections	3 standard reflections every 60 min
1665 independent reflections	intensity decay: none
1481 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.110	Δρ_max = 0.21 e Å⁻³
S = 1.17	Δρ_min = −0.26 e Å⁻³
1665 reflections	Absolute structure: Flack (1983)
228 parameters	Absolute structure parameter: 0.06 (11)
1 restraint

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	Occ. (<1)
Cl1	0.32517 (7)	0.02913 (19)	0.09205 (6)	0.0528 (3)
O1	0.2394 (3)	−0.0572 (11)	0.0241 (3)	0.1091 (18)
O3	0.2751 (5)	0.0918 (11)	0.1838 (3)	0.1308 (19)
O2	0.3962 (13)	0.197 (4)	0.0469 (13)	0.112 (6)	0.65 (5)
O4	0.4124 (9)	−0.132 (3)	0.133 (2)	0.124 (6)	0.65 (5)
O2'	0.368 (5)	0.231 (7)	0.055 (3)	0.178 (16)	0.35 (5)
O4'	0.4038 (19)	−0.147 (4)	0.084 (3)	0.112 (7)	0.35 (5)
O1A	0.4708 (3)	0.4853 (5)	0.3769 (2)	0.0628 (8)
O1B	0.3434 (3)	0.3121 (4)	0.4765 (2)	0.0605 (8)
C11	0.3832 (3)	0.4873 (6)	0.4311 (2)	0.0385 (8)
C12	0.3191 (3)	0.7135 (6)	0.4498 (3)	0.0335 (7)
H12	0.3297	0.7530	0.5222	0.040*
N11	0.3775 (2)	0.8941 (5)	0.3884 (2)	0.0380 (6)
H11A	0.3410	1.0276	0.3980	0.057*
H11B	0.3728	0.8567	0.3225	0.057*
H11C	0.4536	0.9061	0.4079	0.057*
C13	0.1852 (3)	0.6948 (7)	0.4259 (3)	0.0516 (9)
H13	0.1543	0.5767	0.4715	0.062*
C14	0.1204 (4)	0.9175 (10)	0.4518 (5)	0.0815 (16)
H14A	0.1406	0.9619	0.5206	0.122*
H14B	0.0359	0.8940	0.4454	0.122*
H14C	0.1439	1.0362	0.4056	0.122*
C15	0.1584 (4)	0.6139 (10)	0.3180 (4)	0.0811 (15)
H15A	0.0738	0.6049	0.3069	0.122*
H15B	0.1930	0.4651	0.3082	0.122*
H15C	0.1914	0.7202	0.2704	0.122*
O2A	0.3947 (2)	0.5095 (6)	0.69524 (19)	0.0576 (7)
O2B	0.2391 (3)	0.2967 (6)	0.6483 (2)	0.0647 (8)
H2B	0.2688	0.3051	0.5918	0.097*
C21	0.3045 (3)	0.4107 (7)	0.7145 (3)	0.0437 (8)
C22	0.2528 (3)	0.4105 (7)	0.8206 (3)	0.0421 (8)
H22	0.2531	0.2517	0.8452	0.050*
N21	0.3369 (2)	0.5432 (7)	0.88663 (19)	0.0498 (7)
H21A	0.3103	0.5470	0.9501	0.075*
H21B	0.3428	0.6856	0.8628	0.075*
H21C	0.4082	0.4766	0.8866	0.075*
C23	0.1250 (3)	0.4973 (9)	0.8235 (3)	0.0602 (10)
H23	0.0779	0.4046	0.7749	0.072*
C24	0.0737 (4)	0.4601 (13)	0.9282 (5)	0.097 (2)
H24A	0.0825	0.3019	0.9472	0.145*
H24B	−0.0092	0.5001	0.9265	0.145*
H24C	0.1153	0.5548	0.9772	0.145*
C25	0.1139 (5)	0.7465 (11)	0.7894 (5)	0.0901 (17)
H25A	0.0322	0.7935	0.7922	0.135*
H25B	0.1410	0.7612	0.7207	0.135*
H25C	0.1616	0.8418	0.8340	0.135*
OW1	0.5770 (3)	0.4660 (5)	0.1852 (2)	0.0578 (8)
HW1	0.519 (4)	0.503 (12)	0.153 (4)	0.083 (17)*
HW2	0.543 (4)	0.449 (10)	0.245 (4)	0.068 (14)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0524 (5)	0.0638 (6)	0.0419 (4)	−0.0023 (5)	−0.0037 (3)	0.0025 (5)
O1	0.0665 (18)	0.177 (5)	0.083 (2)	−0.021 (3)	−0.0084 (16)	−0.043 (3)
O3	0.189 (4)	0.139 (5)	0.066 (2)	0.002 (4)	0.039 (2)	−0.020 (3)
O2	0.102 (7)	0.150 (14)	0.084 (7)	−0.070 (7)	−0.020 (5)	0.042 (7)
O4	0.080 (4)	0.120 (8)	0.170 (13)	−0.019 (6)	−0.060 (6)	0.065 (8)
O2'	0.29 (4)	0.113 (17)	0.13 (2)	−0.04 (2)	−0.08 (2)	0.096 (17)
O4'	0.095 (10)	0.111 (11)	0.127 (17)	0.067 (11)	−0.059 (10)	−0.042 (12)
O1A	0.0708 (16)	0.0456 (17)	0.0731 (17)	0.0148 (14)	0.0253 (14)	−0.0042 (14)
O1B	0.107 (2)	0.0256 (13)	0.0498 (15)	0.0036 (15)	0.0198 (15)	0.0005 (12)
C11	0.0523 (17)	0.0316 (18)	0.0315 (14)	0.0059 (15)	−0.0015 (13)	−0.0056 (14)
C12	0.0405 (16)	0.0248 (15)	0.0353 (16)	0.0001 (14)	0.0034 (13)	−0.0006 (13)
N11	0.0407 (13)	0.0269 (13)	0.0466 (15)	−0.0021 (12)	0.0059 (11)	−0.0032 (11)
C13	0.0384 (17)	0.0375 (19)	0.079 (3)	−0.0039 (16)	0.0071 (17)	0.0009 (18)
C14	0.046 (2)	0.068 (3)	0.131 (4)	0.016 (2)	0.009 (2)	−0.015 (3)
C15	0.070 (3)	0.075 (3)	0.097 (3)	−0.010 (3)	−0.032 (2)	−0.015 (3)
O2A	0.0586 (14)	0.0598 (16)	0.0550 (13)	−0.0118 (16)	0.0198 (11)	−0.0046 (15)
O2B	0.0749 (18)	0.071 (2)	0.0489 (14)	−0.0180 (17)	0.0104 (12)	−0.0075 (16)
C21	0.0466 (17)	0.0368 (17)	0.0480 (18)	0.0015 (16)	0.0106 (15)	0.0026 (16)
C22	0.0404 (16)	0.0381 (17)	0.0481 (18)	0.0022 (16)	0.0085 (13)	0.0084 (16)
N21	0.0476 (14)	0.060 (2)	0.0420 (13)	0.0017 (17)	0.0038 (11)	0.0070 (16)
C23	0.0392 (16)	0.067 (3)	0.075 (2)	0.004 (2)	0.0068 (15)	−0.007 (3)
C24	0.063 (3)	0.105 (5)	0.125 (4)	−0.003 (3)	0.053 (3)	−0.006 (4)
C25	0.075 (3)	0.079 (4)	0.116 (4)	0.038 (3)	−0.015 (3)	0.008 (3)
OW1	0.0605 (16)	0.058 (2)	0.0550 (15)	−0.0017 (14)	0.0053 (13)	0.0006 (14)

Geometric parameters (Å, º) top

Cl1—O4'	1.360 (17)	C15—H15C	0.9600
Cl1—O2'	1.37 (3)	O2A—C21	1.197 (4)
Cl1—O3	1.387 (4)	O2B—C21	1.305 (5)
Cl1—O1	1.391 (4)	O2B—H2B	0.8200
Cl1—O2	1.402 (12)	C21—C22	1.519 (5)
Cl1—O4	1.456 (11)	C22—N21	1.485 (5)
O1A—C11	1.225 (4)	C22—C23	1.523 (5)
O1B—C11	1.268 (4)	C22—H22	0.9800
C11—C12	1.525 (5)	N21—H21A	0.8900
C12—N11	1.486 (4)	N21—H21B	0.8900
C12—C13	1.534 (5)	N21—H21C	0.8900
C12—H12	0.9800	C23—C24	1.515 (7)
N11—H11A	0.8900	C23—C25	1.524 (8)
N11—H11B	0.8900	C23—H23	0.9800
N11—H11C	0.8900	C24—H24A	0.9600
C13—C15	1.513 (6)	C24—H24B	0.9600
C13—C14	1.531 (6)	C24—H24C	0.9600
C13—H13	0.9800	C25—H25A	0.9600
C14—H14A	0.9600	C25—H25B	0.9600
C14—H14B	0.9600	C25—H25C	0.9600
C14—H14C	0.9600	OW1—HW1	0.80 (5)
C15—H15A	0.9600	OW1—HW2	0.89 (5)
C15—H15B	0.9600

O4'—Cl1—O2'	113 (2)	C13—C15—H15A	109.5
O4'—Cl1—O3	122.7 (16)	C13—C15—H15B	109.5
O2'—Cl1—O3	104 (2)	H15A—C15—H15B	109.5
O4'—Cl1—O1	96.9 (11)	C13—C15—H15C	109.5
O2'—Cl1—O1	109.2 (16)	H15A—C15—H15C	109.5
O3—Cl1—O1	111.2 (3)	H15B—C15—H15C	109.5
O4'—Cl1—O2	96.8 (13)	C21—O2B—H2B	109.5
O2'—Cl1—O2	16 (3)	O2A—C21—O2B	124.9 (3)
O3—Cl1—O2	115.3 (9)	O2A—C21—C22	122.4 (3)
O1—Cl1—O2	112.1 (7)	O2B—C21—C22	112.7 (3)
O4'—Cl1—O4	26.6 (9)	N21—C22—C21	106.3 (3)
O2'—Cl1—O4	117 (2)	N21—C22—C23	113.6 (3)
O3—Cl1—O4	97.5 (12)	C21—C22—C23	113.7 (3)
O1—Cl1—O4	117.0 (10)	N21—C22—H22	107.6
O2—Cl1—O4	103.0 (9)	C21—C22—H22	107.6
O1A—C11—O1B	124.0 (3)	C23—C22—H22	107.6
O1A—C11—C12	119.3 (3)	C22—N21—H21A	109.5
O1B—C11—C12	116.7 (3)	C22—N21—H21B	109.5
N11—C12—C11	108.1 (2)	H21A—N21—H21B	109.5
N11—C12—C13	112.5 (3)	C22—N21—H21C	109.5
C11—C12—C13	111.7 (3)	H21A—N21—H21C	109.5
N11—C12—H12	108.1	H21B—N21—H21C	109.5
C11—C12—H12	108.1	C24—C23—C22	110.6 (4)
C13—C12—H12	108.1	C24—C23—C25	111.8 (5)
C12—N11—H11A	109.5	C22—C23—C25	112.4 (4)
C12—N11—H11B	109.5	C24—C23—H23	107.3
H11A—N11—H11B	109.5	C22—C23—H23	107.3
C12—N11—H11C	109.5	C25—C23—H23	107.3
H11A—N11—H11C	109.5	C23—C24—H24A	109.5
H11B—N11—H11C	109.5	C23—C24—H24B	109.5
C15—C13—C14	112.7 (4)	H24A—C24—H24B	109.5
C15—C13—C12	112.7 (3)	C23—C24—H24C	109.5
C14—C13—C12	111.3 (3)	H24A—C24—H24C	109.5
C15—C13—H13	106.5	H24B—C24—H24C	109.5
C14—C13—H13	106.5	C23—C25—H25A	109.5
C12—C13—H13	106.5	C23—C25—H25B	109.5
C13—C14—H14A	109.5	H25A—C25—H25B	109.5
C13—C14—H14B	109.5	C23—C25—H25C	109.5
H14A—C14—H14B	109.5	H25A—C25—H25C	109.5
C13—C14—H14C	109.5	H25B—C25—H25C	109.5
H14A—C14—H14C	109.5	HW1—OW1—HW2	98 (4)
H14B—C14—H14C	109.5

O1A—C11—C12—N11	3.5 (4)	O2A—C21—C22—N21	−1.8 (5)
O1B—C11—C12—N11	−178.7 (3)	O2B—C21—C22—N21	179.4 (3)
O1A—C11—C12—C13	127.7 (3)	O2A—C21—C22—C23	124.0 (4)
O1B—C11—C12—C13	−54.4 (4)	O2B—C21—C22—C23	−54.8 (5)
N11—C12—C13—C15	65.7 (4)	N21—C22—C23—C24	−66.4 (5)
C11—C12—C13—C15	−56.1 (5)	C21—C22—C23—C24	171.8 (4)
N11—C12—C13—C14	−62.1 (4)	N21—C22—C23—C25	59.3 (5)
C11—C12—C13—C14	176.1 (4)	C21—C22—C23—C25	−62.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11A···O1Bⁱ	0.89	1.95	2.727 (4)	145
N11—H11B···O3ⁱ	0.89	2.51	3.113 (6)	126
N11—H11B···O4ⁱ	0.89	2.53	3.37 (3)	159
N11—H11C···O2Aⁱⁱ	0.89	2.28	2.886 (4)	125
O2B—H2B···O1B	0.82	1.74	2.562 (4)	175
N21—H21A···O2′ⁱⁱⁱ	0.89	2.38	2.87 (3)	115
N21—H21A···O1^iv	0.89	2.63	3.156 (6)	118
N21—H21B···OW1ⁱⁱ	0.89	1.98	2.818 (5)	157
N21—H21C···O4ⁱⁱ	0.89	2.13	3.013 (11)	169
N21—H21C···O4′ⁱⁱ	0.89	2.26	3.13 (2)	168
OW1—HW1···O4ⁱ	0.80 (5)	2.45 (7)	3.050 (12)	133 (6)
OW1—HW1···O4′ⁱ	0.80 (5)	2.57 (7)	3.24 (3)	143 (6)
OW1—HW1···O2	0.80 (5)	2.63 (6)	3.115 (15)	120 (6)
OW1—HW1···O2′	0.80 (5)	2.63 (7)	3.18 (4)	127 (6)
OW1—HW2···O1A	0.89 (5)	1.93 (5)	2.806 (4)	167 (5)

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

Experimental details

Crystal data
Chemical formula	C₅H₁₁NO₂⁺·ClO₄⁻·C₅H₁₂NO₂·H₂O
M_r	352.77
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	11.235 (3), 5.8312 (14), 13.0948 (19)
β (°)	91.282 (16)
V (Å³)	857.7 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.25 × 0.23 × 0.13

Data collection
Diffractometer	Enraf-Nonius sealed tube diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	1751, 1665, 1481
R_int	0.011
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.110, 1.17
No. of reflections	1665
No. of parameters	228
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.26
Absolute structure	Flack (1983)
Absolute structure parameter	0.06 (11)

Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 1999), SHELXL97.

Selected geometric parameters (Å, º) top

O1A—C11	1.225 (4)	O2A—C21	1.197 (4)
O1B—C11	1.268 (4)	O2B—C21	1.305 (5)

O1A—C11—C12—N11	3.5 (4)	O2A—C21—C22—N21	−1.8 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11A···O1Bⁱ	0.89	1.95	2.727 (4)	144.8
N11—H11B···O3ⁱ	0.89	2.51	3.113 (6)	125.7
N11—H11B···O4ⁱ	0.89	2.53	3.37 (3)	159.3
N11—H11C···O2Aⁱⁱ	0.89	2.28	2.886 (4)	125.3
O2B—H2B···O1B	0.82	1.74	2.562 (4)	175.0
N21—H21A···O2'ⁱⁱⁱ	0.89	2.38	2.87 (3)	115.2
N21—H21A···O1^iv	0.89	2.63	3.156 (6)	118.4
N21—H21B···OW1ⁱⁱ	0.89	1.98	2.818 (5)	157.1
N21—H21C···O4ⁱⁱ	0.89	2.13	3.013 (11)	169.1
N21—H21C···O4'ⁱⁱ	0.89	2.26	3.13 (2)	168.0
OW1—HW1···O4ⁱ	0.80 (5)	2.45 (7)	3.050 (12)	133 (6)
OW1—HW1···O4'ⁱ	0.80 (5)	2.57 (7)	3.24 (3)	143 (6)
OW1—HW1···O2	0.80 (5)	2.63 (6)	3.115 (15)	120 (6)
OW1—HW1···O2'	0.80 (5)	2.63 (7)	3.18 (4)	127 (6)
OW1—HW2···O1A	0.89 (5)	1.93 (5)	2.806 (4)	167 (5)

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

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		RefMan
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		CIF
		SGML
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		Plain Text

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