Crystal structure of 1-(5-amino-2H-tetra­zol-2-yl)-2-methyl­propan-2-ol

Park, H.S.; Ryu, J.Y.; Lee, J.

doi:10.1107/S2056989015023713

organic compounds

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ISSN: 2056-9890

Volume 71| Part 12| December 2015| Pages o1057-o1058

https://doi.org/10.1107/S2056989015023713

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Crystal structure of 1-(5-amino-2H-tetrazol-2-yl)-2-methylpropan-2-ol

Hyun Sik Park,^a Ji Yeon Ryu ^a and Junseong Lee ^a ^*

^aDepartment of Chemistry, Chonnam National University, Gwangju 500-757, Republic of Korea
^*Correspondence e-mail: leespy@jnu.ac.kr

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 5 December 2015; accepted 10 December 2015; online 16 December 2015)

The title compound, C₅H₁₁N₅O, crystallized with two independent molecules in the asymmetric unit. The two molecules differ in the orientation of the 2-methylpropan-2-ol unit, with the hydroxy H atoms pointing in opposite directions. In the crystal, molecules are linked via O—H⋯O and N—H⋯O hydrogen bonds, forming ribbons propagating along [10-1]. The ribbons are linked via N—H⋯N hydrogen bonds, forming a three-dimensional structure.

Keywords: crystal structure; 5-aminotetrazole; 2-methylpropan-2-ol; hydrogen bonding.

CCDC reference: 1441577

1. Related literature

For the crystal structure of 5-aminotetrazole monohydrate, see: Britts & Karle (1967 ); and for that of 5-aminotetrazole, see: Fujihisa et al. (2011 ). For the crystal structures of alkali salts of 5-aminotetrazole, see: Ernst et al. (2007 ). For the crystal structure of 5-azido-1H-tetrazole, a highly explosive compound, see: Stierstorfer et al. (2008 ). For some examples of the use of 5-aminotetrazole in the synthesis of metal–organic frameworks, see: Karaghiosoff et al. (2009 ); Liu et al. (2013 ).

2. Experimental

2.1. Crystal data

C₅H₁₁N₅O
M_r = 157.19
Triclinic, $[P \overline 1]$
a = 8.2472 (19) Å
b = 9.731 (2) Å
c = 10.087 (2) Å
α = 90.30 (1)°
β = 96.228 (10)°
γ = 96.259 (10)°
V = 799.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.12 × 0.10 × 0.08 mm

2.2. Data collection

Bruker SMART 1K CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2006 ) T_min = 0.90, T_max = 0.95
11190 measured reflections
2953 independent reflections
2148 reflections with I > 2σ(I)
R_int = 0.047

2.3. Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.122
S = 1.06
2953 reflections
227 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O2ⁱ	0.91 (3)	2.04 (3)	2.946 (2)	171 (2)
N1—H1A⋯O2ⁱⁱ	0.92 (2)	2.53 (2)	3.243 (2)	135 (2)
N1—H1A⋯N9ⁱⁱ	0.92 (2)	2.58 (2)	3.287 (3)	134 (2)
N1—H1B⋯N10ⁱⁱⁱ	0.84 (2)	2.24 (2)	3.082 (2)	173 (2)
O2—H2O⋯N2ⁱⁱ	0.82 (3)	2.14 (3)	2.930 (2)	162 (3)
N6—H6A⋯O1^iv	0.93 (2)	2.22 (2)	3.114 (3)	161 (2)
N6—H6B⋯N5^v	0.82 (2)	2.41 (2)	3.213 (2)	167 (2)
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+1, -z+2; (iii) x, y, z+1; (iv) -x, -y+1, -z+1; (v) x, y, z-1.

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ); molecular graphics: Mercury (Macrae et al., 2008 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL2014 and PLATON.

Supporting information

CCDC reference: 1441577

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S2056989015023713/su5257sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015023713/su5257Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015023713/su5257Isup3.cml

checkCIF report

Comments top

Tetrazole compounds are useful building blocks for the construction of high dimensional metal-organic frameworks, and they have provided various binding modes toward metal centers (Karaghiosoff et al., 2009; Liu et al., 2013). The title compound was easily prepared by the reaction of 5-aminotetrazole and iso-butylene oxide, and introduces an hydroxyl group which we hope will be useful as an additional coordination center.

The title compound, Fig. 1, crystallized with two independent molecules(A and B) in the asymmetric unit. The two molecules differ in the orientation of the 2-methylpropan-2-ol unit, with the hydroxyl H atoms pointing in opposite directions (Fig. 2).

In the crystal, molecules are linked via O—H···O and N—H···O hydrogen bonds (Table 1) forming ribbons propagating along direction [101]. The ribbons are linked via N—H···N hydrogen bonds forming a three-dimensional structure (Table 1 and Fig. 3).

Synthesis and crystallization top

The title compound was synthesized by heating 5-aminotetrazole with an excess amount of iso-butylene oxide, without solvent, at 333 K. Crystals were obtained on cooling the reaction mixture.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. The OH and NH₂ H atoms were located in difference Fourier maps and freely refined. The C-bound H atoms were positioned geometrically and refined using a riding model: C—H = 0.96-0.97 Å with U_iso(H) = 1.5U_eq(C-methyl) and 1.2U_eq(C) for other H atoms.

Related literature top

For the crystal structure of 5-aminotetrazole monohydrate, see: Britts & Karle (1967); and for that of 5-aminotetrazole, see: Fujihisa et al. (2011). For the crystal structures of alkali salts of 5-aminotetrazole, see: Ernst et al. (2007). For the crystal structure of 5-azido-1H-tetrazole, a highly explosive compound, see: Stierstorfer et al. (2008). For some examples of the use of 5-aminotetrazole in the synthesis of metal–organic frameworks, see: Karaghiosoff et al. (2009); Liu et al. (2013).

Structure description top

For the crystal structure of 5-aminotetrazole monohydrate, see: Britts & Karle (1967); and for that of 5-aminotetrazole, see: Fujihisa et al. (2011). For the crystal structures of alkali salts of 5-aminotetrazole, see: Ernst et al. (2007). For the crystal structure of 5-azido-1H-tetrazole, a highly explosive compound, see: Stierstorfer et al. (2008). For some examples of the use of 5-aminotetrazole in the synthesis of metal–organic frameworks, see: Karaghiosoff et al. (2009); Liu et al. (2013).

Synthesis and crystallization top

The title compound was synthesized by heating 5-aminotetrazole with an excess amount of iso-butylene oxide, without solvent, at 333 K. Crystals were obtained on cooling the reaction mixture.

Refinement details top

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the two independent molecules (A and B) of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view of the molecular overlap of molecules A (black) and B (red); calculated using the AutoMolfit routine in PLATON (Spek, 2009).
	Fig. 3. A view along the c axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1). H atoms not involved in hydrogen bonding have been omitted for clarity.

1-(5-Amino-2H-tetrazol-2-yl)-2-methylpropan-2-ol top

Crystal data top

C₅H₁₁N₅O	Z = 4
M_r = 157.19	F(000) = 336
Triclinic, P1	D_x = 1.305 Mg m⁻³
a = 8.2472 (19) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.731 (2) Å	Cell parameters from 4382 reflections
c = 10.087 (2) Å	θ = 2.0–29.9°
α = 90.30 (1)°	µ = 0.10 mm⁻¹
β = 96.228 (10)°	T = 296 K
γ = 96.259 (10)°	Block, colourless
V = 799.8 (3) Å³	0.12 × 0.10 × 0.08 mm

Data collection top

Bruker SMART 1K CCD diffractometer	2953 independent reflections
Radiation source: fine-focus sealed tube	2148 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
profile data from ω scans	θ_max = 25.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −9→9
T_min = 0.90, T_max = 0.95	k = −11→11
11190 measured reflections	l = −12→12

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.122	w = 1/[σ²(F_o²) + (0.0588P)² + 0.018P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2953 reflections	Δρ_max = 0.17 e Å⁻³
227 parameters	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₅H₁₁N₅O	γ = 96.259 (10)°
M_r = 157.19	V = 799.8 (3) Å³
Triclinic, P1	Z = 4
a = 8.2472 (19) Å	Mo Kα radiation
b = 9.731 (2) Å	µ = 0.10 mm⁻¹
c = 10.087 (2) Å	T = 296 K
α = 90.30 (1)°	0.12 × 0.10 × 0.08 mm
β = 96.228 (10)°

Data collection top

Bruker SMART 1K CCD diffractometer	2953 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2006)	2148 reflections with I > 2σ(I)
T_min = 0.90, T_max = 0.95	R_int = 0.047
11190 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.17 e Å⁻³
2953 reflections	Δρ_min = −0.19 e Å⁻³
227 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.28249 (16)	0.86314 (15)	0.81161 (14)	0.0536 (4)
H1O	0.270 (3)	0.952 (3)	0.789 (3)	0.101 (9)*
N1	0.4219 (2)	0.6570 (2)	1.28100 (17)	0.0530 (5)
H1A	0.527 (3)	0.690 (2)	1.315 (2)	0.063 (7)*
H1B	0.378 (2)	0.592 (2)	1.3251 (19)	0.048 (6)*
N2	0.48661 (17)	0.69286 (15)	1.05833 (15)	0.0405 (4)
N3	0.40258 (18)	0.64638 (14)	0.94250 (14)	0.0383 (4)
N4	0.26829 (19)	0.56520 (15)	0.95690 (15)	0.0463 (4)
N5	0.25930 (18)	0.55592 (16)	1.08764 (15)	0.0458 (4)
C1	0.3924 (2)	0.63485 (18)	1.14668 (18)	0.0376 (4)
C2	0.4501 (2)	0.68157 (18)	0.80986 (18)	0.0456 (5)
H2A	0.3810	0.6223	0.7440	0.055*
H2B	0.5624	0.6622	0.8062	0.055*
C3	0.4370 (2)	0.83230 (18)	0.77215 (18)	0.0432 (5)
C4	0.5765 (2)	0.9290 (2)	0.8434 (2)	0.0572 (6)
H4A	0.5651	1.0223	0.8165	0.086*
H4B	0.6794	0.9034	0.8208	0.086*
H4C	0.5732	0.9226	0.9380	0.086*
C5	0.4359 (3)	0.8413 (2)	0.6213 (2)	0.0730 (7)
H5A	0.3447	0.7815	0.5786	0.110*
H5B	0.5363	0.8133	0.5957	0.110*
H5C	0.4260	0.9348	0.5945	0.110*
O2	0.24050 (17)	0.15721 (15)	0.77069 (15)	0.0509 (4)
H2O	0.301 (4)	0.198 (3)	0.831 (3)	0.131 (13)*
N6	0.0533 (3)	0.3192 (2)	0.24056 (16)	0.0523 (5)
H6A	−0.054 (3)	0.283 (2)	0.214 (2)	0.065 (7)*
H6B	0.093 (2)	0.377 (2)	0.191 (2)	0.057 (7)*
N7	0.00343 (18)	0.29922 (16)	0.46818 (14)	0.0436 (4)
N8	0.09725 (18)	0.34753 (14)	0.57877 (14)	0.0382 (4)
N9	0.23381 (19)	0.42091 (16)	0.55631 (15)	0.0505 (4)
N10	0.23478 (19)	0.42088 (17)	0.42439 (15)	0.0516 (5)
C6	0.0940 (2)	0.34662 (18)	0.37369 (17)	0.0377 (4)
C7	0.0495 (2)	0.32626 (18)	0.71339 (17)	0.0416 (5)
H7A	−0.0649	0.3416	0.7126	0.050*
H7B	0.1138	0.3952	0.7729	0.050*
C8	0.0714 (2)	0.18313 (18)	0.76967 (17)	0.0386 (4)
C9	0.0260 (3)	0.1839 (2)	0.9121 (2)	0.0652 (7)
H9A	0.0504	0.0992	0.9542	0.098*
H9B	−0.0891	0.1923	0.9108	0.098*
H9C	0.0881	0.2607	0.9610	0.098*
C10	−0.0294 (3)	0.0686 (2)	0.6850 (2)	0.0573 (6)
H10A	0.0133	0.0630	0.6005	0.086*
H10B	−0.1416	0.0880	0.6710	0.086*
H10C	−0.0237	−0.0178	0.7298	0.086*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0434 (8)	0.0474 (9)	0.0716 (10)	0.0081 (7)	0.0097 (7)	0.0127 (7)
N1	0.0503 (12)	0.0632 (12)	0.0421 (11)	−0.0055 (10)	0.0018 (9)	0.0068 (9)
N2	0.0397 (9)	0.0411 (9)	0.0389 (9)	0.0004 (7)	0.0010 (7)	0.0029 (7)
N3	0.0432 (9)	0.0329 (8)	0.0379 (9)	0.0030 (7)	0.0023 (7)	0.0032 (7)
N4	0.0500 (10)	0.0425 (9)	0.0436 (10)	−0.0031 (8)	0.0008 (7)	0.0055 (7)
N5	0.0436 (10)	0.0482 (10)	0.0436 (10)	−0.0011 (8)	0.0021 (7)	0.0076 (7)
C1	0.0356 (10)	0.0374 (10)	0.0395 (11)	0.0052 (8)	0.0015 (8)	0.0049 (8)
C2	0.0558 (12)	0.0436 (11)	0.0389 (11)	0.0073 (9)	0.0095 (9)	0.0002 (9)
C3	0.0446 (11)	0.0401 (11)	0.0454 (11)	0.0035 (9)	0.0083 (9)	0.0069 (9)
C4	0.0513 (13)	0.0492 (13)	0.0705 (15)	−0.0013 (10)	0.0098 (11)	0.0077 (11)
C5	0.0948 (19)	0.0761 (17)	0.0485 (13)	0.0069 (14)	0.0111 (13)	0.0190 (12)
O2	0.0433 (8)	0.0501 (9)	0.0586 (10)	0.0054 (7)	0.0015 (7)	0.0067 (7)
N6	0.0598 (12)	0.0577 (12)	0.0362 (10)	−0.0039 (10)	0.0007 (9)	0.0061 (8)
N7	0.0432 (9)	0.0492 (10)	0.0355 (9)	−0.0032 (7)	−0.0013 (7)	0.0030 (7)
N8	0.0410 (9)	0.0374 (9)	0.0347 (9)	0.0003 (7)	0.0010 (7)	0.0052 (7)
N9	0.0506 (10)	0.0563 (11)	0.0403 (10)	−0.0081 (8)	−0.0015 (8)	0.0093 (8)
N10	0.0489 (10)	0.0637 (11)	0.0390 (9)	−0.0062 (8)	0.0027 (8)	0.0102 (8)
C6	0.0413 (11)	0.0361 (10)	0.0357 (10)	0.0051 (8)	0.0030 (8)	0.0059 (8)
C7	0.0529 (12)	0.0379 (11)	0.0348 (10)	0.0059 (9)	0.0078 (9)	0.0018 (8)
C8	0.0396 (11)	0.0383 (11)	0.0380 (10)	0.0031 (8)	0.0056 (8)	0.0049 (8)
C9	0.0835 (17)	0.0633 (15)	0.0513 (13)	0.0076 (12)	0.0191 (12)	0.0159 (11)
C10	0.0582 (14)	0.0447 (12)	0.0648 (14)	−0.0055 (10)	−0.0005 (11)	0.0037 (10)

Geometric parameters (Å, º) top

O1—C3	1.437 (2)	O2—C8	1.443 (2)
O1—H1O	0.91 (3)	O2—H2O	0.82 (3)
N1—C1	1.362 (2)	N6—C6	1.366 (2)
N1—H1A	0.92 (2)	N6—H6A	0.93 (2)
N1—H1B	0.844 (19)	N6—H6B	0.82 (2)
N2—C1	1.333 (2)	N7—C6	1.328 (2)
N2—N3	1.342 (2)	N7—N8	1.339 (2)
N3—N4	1.310 (2)	N8—N9	1.308 (2)
N3—C2	1.466 (2)	N8—C7	1.464 (2)
N4—N5	1.332 (2)	N9—N10	1.332 (2)
N5—C1	1.349 (2)	N10—C6	1.347 (2)
C2—C3	1.529 (3)	C7—C8	1.528 (2)
C2—H2A	0.9700	C7—H7A	0.9700
C2—H2B	0.9700	C7—H7B	0.9700
C3—C4	1.518 (3)	C8—C10	1.515 (3)
C3—C5	1.524 (3)	C8—C9	1.524 (2)
C4—H4A	0.9600	C9—H9A	0.9600
C4—H4B	0.9600	C9—H9B	0.9600
C4—H4C	0.9600	C9—H9C	0.9600
C5—H5A	0.9600	C10—H10A	0.9600
C5—H5B	0.9600	C10—H10B	0.9600
C5—H5C	0.9600	C10—H10C	0.9600

C3—O1—H1O	107.4 (15)	C8—O2—H2O	113 (2)
C1—N1—H1A	117.3 (13)	C6—N6—H6A	116.9 (13)
C1—N1—H1B	113.0 (14)	C6—N6—H6B	114.9 (15)
H1A—N1—H1B	114.2 (18)	H6A—N6—H6B	115.5 (19)
C1—N2—N3	101.66 (14)	C6—N7—N8	101.56 (14)
N4—N3—N2	113.70 (14)	N9—N8—N7	114.12 (14)
N4—N3—C2	121.24 (15)	N9—N8—C7	122.32 (15)
N2—N3—C2	125.06 (14)	N7—N8—C7	123.51 (14)
N3—N4—N5	106.41 (14)	N8—N9—N10	105.90 (15)
N4—N5—C1	105.97 (13)	N9—N10—C6	106.18 (14)
N2—C1—N5	112.25 (16)	N7—C6—N10	112.23 (16)
N2—C1—N1	124.33 (17)	N7—C6—N6	124.23 (18)
N5—C1—N1	123.35 (16)	N10—C6—N6	123.49 (16)
N3—C2—C3	114.27 (14)	N8—C7—C8	114.86 (14)
N3—C2—H2A	108.7	N8—C7—H7A	108.6
C3—C2—H2A	108.7	C8—C7—H7A	108.6
N3—C2—H2B	108.7	N8—C7—H7B	108.6
C3—C2—H2B	108.7	C8—C7—H7B	108.6
H2A—C2—H2B	107.6	H7A—C7—H7B	107.5
O1—C3—C4	110.33 (16)	O2—C8—C10	106.22 (15)
O1—C3—C5	110.39 (16)	O2—C8—C9	109.55 (15)
C4—C3—C5	111.14 (16)	C10—C8—C9	112.03 (15)
O1—C3—C2	105.38 (14)	O2—C8—C7	109.61 (13)
C4—C3—C2	111.81 (16)	C10—C8—C7	112.28 (15)
C5—C3—C2	107.60 (16)	C9—C8—C7	107.14 (15)
C3—C4—H4A	109.5	C8—C9—H9A	109.5
C3—C4—H4B	109.5	C8—C9—H9B	109.5
H4A—C4—H4B	109.5	H9A—C9—H9B	109.5
C3—C4—H4C	109.5	C8—C9—H9C	109.5
H4A—C4—H4C	109.5	H9A—C9—H9C	109.5
H4B—C4—H4C	109.5	H9B—C9—H9C	109.5
C3—C5—H5A	109.5	C8—C10—H10A	109.5
C3—C5—H5B	109.5	C8—C10—H10B	109.5
H5A—C5—H5B	109.5	H10A—C10—H10B	109.5
C3—C5—H5C	109.5	C8—C10—H10C	109.5
H5A—C5—H5C	109.5	H10A—C10—H10C	109.5
H5B—C5—H5C	109.5	H10B—C10—H10C	109.5

C1—N2—N3—N4	−0.60 (19)	C6—N7—N8—N9	1.0 (2)
C1—N2—N3—C2	178.59 (15)	C6—N7—N8—C7	178.36 (15)
N2—N3—N4—N5	0.2 (2)	N7—N8—N9—N10	−1.1 (2)
C2—N3—N4—N5	−178.98 (14)	C7—N8—N9—N10	−178.47 (14)
N3—N4—N5—C1	0.23 (19)	N8—N9—N10—C6	0.6 (2)
N3—N2—C1—N5	0.74 (19)	N8—N7—C6—N10	−0.5 (2)
N3—N2—C1—N1	−176.40 (17)	N8—N7—C6—N6	177.00 (17)
N4—N5—C1—N2	−0.6 (2)	N9—N10—C6—N7	−0.1 (2)
N4—N5—C1—N1	176.53 (17)	N9—N10—C6—N6	−177.61 (17)
N4—N3—C2—C3	110.47 (19)	N9—N8—C7—C8	−104.44 (19)
N2—N3—C2—C3	−68.7 (2)	N7—N8—C7—C8	78.4 (2)
N3—C2—C3—O1	−44.3 (2)	N8—C7—C8—O2	57.7 (2)
N3—C2—C3—C4	75.5 (2)	N8—C7—C8—C10	−60.1 (2)
N3—C2—C3—C5	−162.14 (16)	N8—C7—C8—C9	176.52 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2ⁱ	0.91 (3)	2.04 (3)	2.946 (2)	171 (2)
N1—H1A···O2ⁱⁱ	0.92 (2)	2.53 (2)	3.243 (2)	135 (2)
N1—H1A···N9ⁱⁱ	0.92 (2)	2.58 (2)	3.287 (3)	134 (2)
N1—H1B···N10ⁱⁱⁱ	0.84 (2)	2.24 (2)	3.082 (2)	173 (2)
O2—H2O···N2ⁱⁱ	0.82 (3)	2.14 (3)	2.930 (2)	162 (3)
N6—H6A···O1^iv	0.93 (2)	2.22 (2)	3.114 (3)	161 (2)
N6—H6B···N5^v	0.82 (2)	2.41 (2)	3.213 (2)	167 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2ⁱ	0.91 (3)	2.04 (3)	2.946 (2)	171 (2)
N1—H1A···O2ⁱⁱ	0.92 (2)	2.53 (2)	3.243 (2)	135 (2)
N1—H1A···N9ⁱⁱ	0.92 (2)	2.58 (2)	3.287 (3)	134 (2)
N1—H1B···N10ⁱⁱⁱ	0.84 (2)	2.24 (2)	3.082 (2)	173 (2)
O2—H2O···N2ⁱⁱ	0.82 (3)	2.14 (3)	2.930 (2)	162 (3)
N6—H6A···O1^iv	0.93 (2)	2.22 (2)	3.114 (3)	161 (2)
N6—H6B···N5^v	0.82 (2)	2.41 (2)	3.213 (2)	167 (2)

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

Acknowledgements

This work was supported by a Chonnam National University research grant in 2014.

References

Britts, K. & Karle, I. L. (1967). Acta Cryst. 22, 308–312. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ernst, V., Klapötke, T. M. & Stierstorfer, J. (2007). Z. Anorg. Allg. Chem. 633, 879–887. Web of Science CSD CrossRef CAS Google Scholar
Fujihisa, H., Honda, K., Obata, S., Yamawaki, H., Takeya, S., Gotoh, Y. & Matsunaga, T. (2011). CrystEngComm, 13, 99–102. Web of Science CSD CrossRef CAS Google Scholar
Karaghiosoff, K., Klapötke, T. M. & Miró Sabaté, C. (2009). Chem. Eur. J. 15, 1164–1176. Web of Science CSD CrossRef PubMed CAS Google Scholar
Liu, Z.-Y., Zou, H.-A., Hou, Z.-J., Yang, E.-C. & Zhao, X.-J. (2013). Dalton Trans. 42, 15716–15725. Web of Science CSD CrossRef CAS PubMed Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stierstorfer, J., Klapötke, T. M., Hammerl, A. & Chapman, R. D. (2008). Z. Anorg. Allg. Chem. 634, 1051–1057. Web of Science CSD CrossRef CAS Google Scholar

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