Polythia­zide

Gelbrich, T.; Haddow, M.F.; Griesser, U.J.

doi:10.1107/S1600536810022105

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Pages o1663-o1664

doi:10.1107/S1600536810022105

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Polythiazide

Thomas Gelbrich,^a ^* Mairi F. Haddow ^a ‡ and Ulrich J. Griesser ^a

^aInstitute of Pharmacy, University of Innsbruck, Innrain 52, 6020 Innsbruck, Austria
^*Correspondence e-mail: thomas.gelbrich@uibk.ac.at

(Received 1 June 2010; accepted 9 June 2010; online 16 June 2010)

The crystal structure of the title compound, C₁₁H₁₃ClF₃N₃O₄S₃ (systematic name: 6-chloro-2-methyl-3-{[(2,2,2-trifluoroethyl)sulfanyl]methyl}-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide; CRN: 346–18–9), exhibits a two-dimensional network of hydrogen-bonded molecules parallel to ( $[\overline{1}]$ 01). The NH and NH₂ groups act as donor sites and the sulfonyl O atoms as acceptor sites in N—H⋯O hydrogen bonds, and a C—H⋯O interaction also occurs. The thiadiazine ring adopts an envelope conformation with the N atom bonded to sulfur at the tip of the flap, and the methyl substituent is in an axial position.

Related literature

For the preparation of polythiazide, see: McManus (1961 ). For a comprehensive description of polythiazide, see: Negendra Vara et al. (1991 ). For a preliminary crystallographic study at room temperature, see Dupont & Dideberg (1970 ). For crystal structures of polymorphs and solvates of related thiazide compounds, see: Zhou et al. (2006 ); Johnston et al. (2007a ,b ); Johnston et al. (2007 ); Fernandes, Florence et al. (2006 ); Fernandes, Shankland et al. (2007 ); Johnston et al. (2008 ); Fabbiani et al. (2007 ); Fernandes, Johnston et al. (2007 ); Fernandes, Leech et al. (2007 ).

Experimental

Crystal data

C₁₁H₁₃ClF₃N₃O₄S₃
M_r = 439.87
Monoclinic, C c
a = 14.6659 (7) Å
b = 9.5498 (6) Å
c = 13.6720 (7) Å
β = 116.149 (3)°
V = 1718.87 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.64 mm⁻¹
T = 120 K
0.12 × 0.10 × 0.06 mm

Data collection

Bruker-Nonius Roper CCD camera on κ-goniostat diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.927, T_max = 0.963
9021 measured reflections
3197 independent reflections
2768 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.098
S = 1.06
3197 reflections
239 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.41 e Å⁻³
Absolute structure: Flack (1983 ), 1504 Friedel pairs
Flack parameter: 0.12 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N⋯O4ⁱ	0.88 (2)	2.21 (4)	2.906 (4)	135 (4)
N2—H1N⋯O1ⁱⁱ	0.88 (2)	2.59 (4)	3.230 (4)	130 (4)
N3—H3N⋯O2ⁱⁱⁱ	0.88 (2)	2.11 (3)	2.929 (5)	154 (5)
C10—H10B⋯O2^iv	0.99	2.31	3.267 (5)	163
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+1, z+{\script{1\over 2}}]$ ; (iii) x, y-1, z; (iv) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810022105/kj2150sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810022105/kj2150Isup2.hkl

checkCIF report

Comment top

The title compound is a thiazide diuretic drug. The asymmetric unit contains a single molecule (see Fig. 1), and the lattice parameters are consistent with a preliminary crystallographic study (Dupont & Dideberg, 1970). The geometrical parameters of the thiazide unit are in concert with other structures of the same class of compounds (see section Related literature). The S2—N3 bond of the sulfonyl group is gauche with respect to the C5—C6 bond of the phenyl ring. The conformation of C—S—C—C side chain of the heterocyclic ring is characterized by the torsions angles N1—C1—C9—S3 = 170.8 (3)°, C1—C9 —S3—C10 = 162.6 (3)° and C9—S3—C10—C11 = 94.5 (4)°.

Each polythiazide molecule is N—H···O bonded to two neighbouring molecules so that a hydrogen bonded sheet parallel to (-101) is formed (see Fig. 2). The NH group and one sulfonamide O atom are engaged in an N2—H···O4(x + 1/2, -y + 1/2) interaction. An N3—H···O2(x, y - 1, z) bond links two molecules via the sulfonamide NH₂ group and a thiazide sulfonyl O atom. Each N—H···O bonded sheet contains an additional short C10—H···O2(x + 1/2, -y + 3/2, z + 1/2) contact (see Table 1). A longer N2—H···O1(x, -y + 1, z + 1/2) contact between neighbouring sheets, in which the NH group is involved again, is also worth mentioning. The closest intermolecular contact of the second NH₂ H atom is to the S atom of the side chain, H2N···S3(x, -y + 1, z - 1/2) = 2.93 (4) Å.

Related literature top

For the preparation of polythiazide, see: McManus (1961). For a comprehensive description of polythiazide, see: Negendra Vara et al. (1991). For a preliminary crystallographic study at room temperature, see Dupont & Dideberg (1970). For crystal structures of polymorphs and solvates of related thiazide compounds, see: Zhou et al. (2006); Johnston et al. (2007a,b); Johnston et al. (2007); Fernandes, Florence et al. (2006); Fernandes, Shankland et al. (2007); Johnston et al. (2008); Fabbiani et al. (2007); Fernandes, Johnston et al. (2007); Fernandes, Leech et al. (2007).

Experimental top

The investigated crystals were obtained from a polythiazide sample from Pfizer (Brussels, Belgium).

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary size.
	Fig. 2. Portion of a hydrogen bonded sheet parallel to (-101) and defined by N—H···O (dashed lines) and additional C—H···O (dotted lines) contacts. H and O atoms directly involved in these interactions are drawn as balls, and hydrogen attached to C atoms are omitted for clarity.

6-chloro-2-methyl-3-{[(2,2,2-trifluoroethyl)sulfanyl]methyl}-3,4-dihydro- 2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide top

Crystal data top

C₁₁H₁₃ClF₃N₃O₄S₃	F(000) = 896
M_r = 439.87	D_x = 1.700 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 11202 reflections
a = 14.6659 (7) Å	θ = 2.9–27.5°
b = 9.5498 (6) Å	µ = 0.64 mm⁻¹
c = 13.6720 (7) Å	T = 120 K
β = 116.149 (3)°	Plate, colourless
V = 1718.87 (16) Å³	0.12 × 0.10 × 0.06 mm
Z = 4

Data collection top

Bruker-Nonius Roper CCD camera on κ-goniostat diffractometer	3197 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode	2768 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
Detector resolution: 9.091 pixels mm^-1	θ_max = 26.0°, θ_min = 3.3°
ϕ & ω scans	h = −17→18
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −11→11
T_min = 0.927, T_max = 0.963	l = −15→16
9021 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.098	w = 1/[σ²(F_o²) + (0.0435P)² + 0.009P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3197 reflections	Δρ_max = 0.32 e Å⁻³
239 parameters	Δρ_min = −0.41 e Å⁻³
5 restraints	Absolute structure: Flack (1983), 1504 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.12 (8)

Crystal data top

C₁₁H₁₃ClF₃N₃O₄S₃	V = 1718.87 (16) Å³
M_r = 439.87	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 14.6659 (7) Å	µ = 0.64 mm⁻¹
b = 9.5498 (6) Å	T = 120 K
c = 13.6720 (7) Å	0.12 × 0.10 × 0.06 mm
β = 116.149 (3)°

Data collection top

Bruker-Nonius Roper CCD camera on κ-goniostat diffractometer	3197 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	2768 reflections with I > 2σ(I)
T_min = 0.927, T_max = 0.963	R_int = 0.055
9021 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.098	Δρ_max = 0.32 e Å⁻³
S = 1.06	Δρ_min = −0.41 e Å⁻³
3197 reflections	Absolute structure: Flack (1983), 1504 Friedel pairs
239 parameters	Absolute structure parameter: 0.12 (8)
5 restraints

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
Cl1	0.88627 (8)	0.03391 (10)	0.90846 (8)	0.0280 (2)
S1	0.94030 (7)	0.63949 (10)	0.76867 (7)	0.0226 (2)
S2	0.77245 (7)	0.12532 (10)	0.65142 (8)	0.0241 (2)
S3	1.04262 (8)	0.75479 (12)	1.17195 (8)	0.0262 (2)
O1	0.9673 (2)	0.6291 (3)	0.6804 (2)	0.0285 (7)
O2	0.8556 (2)	0.7293 (3)	0.7536 (2)	0.0272 (7)
O3	0.7388 (2)	0.2033 (3)	0.5523 (2)	0.0348 (7)
O4	0.6988 (2)	0.0628 (3)	0.6808 (2)	0.0344 (7)
N1	1.0394 (2)	0.6927 (4)	0.8780 (3)	0.0228 (7)
N2	1.0131 (3)	0.5322 (3)	0.9992 (3)	0.0214 (7)
H1N	1.043 (4)	0.502 (6)	1.067 (2)	0.052 (16)*
N3	0.8417 (3)	−0.0017 (4)	0.6449 (3)	0.0255 (8)
H2N	0.892 (3)	0.022 (5)	0.631 (4)	0.050 (16)*
H3N	0.856 (4)	−0.066 (4)	0.696 (3)	0.041 (15)*
C1	1.0167 (3)	0.6786 (4)	0.9736 (3)	0.0233 (9)
H1	0.9479	0.7195	0.9531	0.028*
C2	0.9619 (3)	0.4380 (4)	0.9200 (3)	0.0192 (8)
C3	0.9196 (3)	0.4722 (4)	0.8079 (3)	0.0193 (8)
C4	0.8626 (3)	0.3757 (4)	0.7286 (3)	0.0188 (8)
H4	0.8328	0.4027	0.6541	0.023*
C5	0.8483 (3)	0.2403 (4)	0.7563 (3)	0.0199 (8)
C6	0.8960 (3)	0.2032 (4)	0.8677 (3)	0.0192 (8)
C7	0.9523 (3)	0.2976 (4)	0.9475 (3)	0.0206 (8)
H7	0.9849	0.2686	1.0215	0.025*
C8	1.1391 (3)	0.6397 (5)	0.8917 (3)	0.0289 (10)
H8A	1.1933	0.6981	0.9447	0.043*
H8B	1.1421	0.6430	0.8216	0.043*
H8C	1.1480	0.5428	0.9180	0.043*
C9	1.0919 (3)	0.7580 (4)	1.0712 (3)	0.0251 (9)
H9A	1.0985	0.8557	1.0509	0.030*
H9B	1.1595	0.7129	1.1004	0.030*
C10	1.1529 (3)	0.8004 (6)	1.2942 (3)	0.0360 (11)
H10A	1.1519	0.7472	1.3558	0.043*
H10B	1.2143	0.7715	1.2865	0.043*
C11	1.1605 (4)	0.9502 (6)	1.3201 (4)	0.0438 (13)
F1	1.2461 (3)	0.9823 (5)	1.4089 (3)	0.0842 (14)
F2	1.1618 (3)	1.0300 (4)	1.2398 (3)	0.0708 (10)
F3	1.0838 (2)	0.9967 (4)	1.3395 (3)	0.0656 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0427 (6)	0.0181 (5)	0.0234 (5)	−0.0054 (4)	0.0147 (4)	−0.0008 (4)
S1	0.0297 (5)	0.0179 (5)	0.0215 (5)	0.0026 (4)	0.0125 (4)	0.0038 (4)
S2	0.0276 (5)	0.0226 (6)	0.0185 (5)	−0.0012 (5)	0.0069 (4)	−0.0028 (4)
S3	0.0322 (5)	0.0254 (6)	0.0257 (5)	−0.0050 (4)	0.0172 (4)	−0.0072 (4)
O1	0.0404 (17)	0.0296 (17)	0.0201 (15)	−0.0011 (13)	0.0175 (13)	0.0038 (12)
O2	0.0278 (15)	0.0215 (16)	0.0331 (17)	0.0057 (13)	0.0141 (13)	0.0059 (13)
O3	0.0458 (18)	0.0267 (17)	0.0168 (15)	0.0028 (14)	0.0000 (12)	−0.0001 (12)
O4	0.0300 (16)	0.0406 (19)	0.0346 (18)	−0.0126 (15)	0.0161 (14)	−0.0130 (15)
N1	0.0321 (19)	0.0193 (18)	0.0214 (18)	−0.0022 (15)	0.0157 (15)	−0.0036 (14)
N2	0.0327 (18)	0.0143 (17)	0.0176 (18)	−0.0026 (14)	0.0116 (15)	0.0015 (13)
N3	0.034 (2)	0.020 (2)	0.025 (2)	0.0027 (16)	0.0156 (16)	−0.0014 (15)
C1	0.036 (2)	0.017 (2)	0.021 (2)	−0.0040 (18)	0.0165 (17)	−0.0021 (16)
C2	0.0214 (19)	0.019 (2)	0.017 (2)	0.0023 (16)	0.0083 (16)	−0.0020 (16)
C3	0.024 (2)	0.016 (2)	0.019 (2)	0.0041 (16)	0.0111 (16)	0.0020 (16)
C4	0.0179 (18)	0.019 (2)	0.017 (2)	0.0053 (16)	0.0061 (15)	0.0013 (16)
C5	0.022 (2)	0.019 (2)	0.019 (2)	−0.0006 (17)	0.0092 (17)	−0.0054 (16)
C6	0.0242 (19)	0.017 (2)	0.018 (2)	0.0004 (16)	0.0109 (16)	0.0005 (16)
C7	0.028 (2)	0.019 (2)	0.0131 (19)	−0.0031 (17)	0.0075 (15)	0.0003 (15)
C8	0.021 (2)	0.041 (3)	0.025 (2)	0.0011 (19)	0.0104 (17)	0.0052 (19)
C9	0.032 (2)	0.023 (2)	0.021 (2)	0.0007 (18)	0.0118 (17)	−0.0009 (17)
C10	0.033 (2)	0.054 (3)	0.020 (2)	0.004 (2)	0.0101 (18)	−0.002 (2)
C11	0.040 (3)	0.054 (4)	0.044 (3)	−0.020 (2)	0.024 (2)	−0.021 (3)
F1	0.066 (2)	0.128 (4)	0.062 (2)	−0.063 (2)	0.0310 (18)	−0.056 (2)
F2	0.095 (2)	0.052 (2)	0.072 (2)	−0.0414 (19)	0.043 (2)	−0.0140 (18)
F3	0.069 (2)	0.052 (2)	0.095 (3)	−0.0182 (17)	0.053 (2)	−0.0440 (19)

Geometric parameters (Å, º) top

Cl1—C6	1.736 (4)	C2—C3	1.415 (5)
S1—O1	1.429 (3)	C2—C7	1.416 (6)
S1—O2	1.448 (3)	C3—C4	1.388 (5)
S1—N1	1.640 (3)	C4—C5	1.390 (5)
S1—C3	1.753 (4)	C4—H4	0.9500
S2—O3	1.430 (3)	C5—C6	1.412 (5)
S2—O4	1.437 (3)	C6—C7	1.375 (5)
S2—N3	1.610 (4)	C7—H7	0.9500
S2—C5	1.759 (4)	C8—H8A	0.9800
S3—C10	1.794 (4)	C8—H8B	0.9800
S3—C9	1.816 (4)	C8—H8C	0.9800
N1—C8	1.480 (5)	C9—H9A	0.9900
N1—C1	1.490 (5)	C9—H9B	0.9900
N2—C2	1.353 (5)	C10—C11	1.467 (7)
N2—C1	1.447 (5)	C10—H10A	0.9900
N2—H1N	0.88 (2)	C10—H10B	0.9900
N3—H2N	0.87 (2)	C11—F3	1.340 (6)
N3—H3N	0.884 (19)	C11—F2	1.343 (6)
C1—C9	1.508 (5)	C11—F1	1.343 (6)
C1—H1	1.0000

O1—S1—O2	117.39 (17)	C3—C4—H4	119.5
O1—S1—N1	109.12 (17)	C5—C4—H4	119.5
O2—S1—N1	107.83 (17)	C4—C5—C6	117.7 (3)
O1—S1—C3	110.15 (18)	C4—C5—S2	118.4 (3)
O2—S1—C3	109.29 (18)	C6—C5—S2	123.9 (3)
N1—S1—C3	101.91 (18)	C7—C6—C5	122.0 (4)
O3—S2—O4	119.56 (19)	C7—C6—Cl1	117.5 (3)
O3—S2—N3	107.61 (19)	C5—C6—Cl1	120.5 (3)
O4—S2—N3	105.8 (2)	C6—C7—C2	120.3 (3)
O3—S2—C5	106.11 (18)	C6—C7—H7	119.8
O4—S2—C5	108.34 (18)	C2—C7—H7	119.8
N3—S2—C5	109.11 (19)	N1—C8—H8A	109.5
C10—S3—C9	101.8 (2)	N1—C8—H8B	109.5
C8—N1—C1	116.6 (3)	H8A—C8—H8B	109.5
C8—N1—S1	116.0 (3)	N1—C8—H8C	109.5
C1—N1—S1	108.8 (2)	H8A—C8—H8C	109.5
C2—N2—C1	121.0 (3)	H8B—C8—H8C	109.5
C2—N2—H1N	118 (4)	C1—C9—S3	106.4 (3)
C1—N2—H1N	121 (4)	C1—C9—H9A	110.5
S2—N3—H2N	116 (4)	S3—C9—H9A	110.5
S2—N3—H3N	115 (3)	C1—C9—H9B	110.5
H2N—N3—H3N	115 (5)	S3—C9—H9B	110.5
N2—C1—N1	110.2 (3)	H9A—C9—H9B	108.6
N2—C1—C9	111.2 (3)	C11—C10—S3	113.7 (4)
N1—C1—C9	111.8 (3)	C11—C10—H10A	108.8
N2—C1—H1	107.8	S3—C10—H10A	108.8
N1—C1—H1	107.8	C11—C10—H10B	108.8
C9—C1—H1	107.8	S3—C10—H10B	108.8
N2—C2—C3	122.5 (4)	H10A—C10—H10B	107.7
N2—C2—C7	120.1 (3)	F3—C11—F2	106.8 (5)
C3—C2—C7	117.3 (3)	F3—C11—F1	106.1 (4)
C4—C3—C2	121.2 (4)	F2—C11—F1	105.4 (4)
C4—C3—S1	119.5 (3)	F3—C11—C10	113.0 (4)
C2—C3—S1	119.3 (3)	F2—C11—C10	112.5 (4)
C3—C4—C5	121.1 (3)	F1—C11—C10	112.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N···O4ⁱ	0.88 (2)	2.21 (4)	2.906 (4)	135 (4)
N2—H1N···O1ⁱⁱ	0.88 (2)	2.59 (4)	3.230 (4)	130 (4)
N3—H3N···O2ⁱⁱⁱ	0.88 (2)	2.11 (3)	2.929 (5)	154 (5)
C10—H10B···O2^iv	0.99	2.31	3.267 (5)	163

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x, −y+1, z+1/2; (iii) x, y−1, z; (iv) x+1/2, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₃ClF₃N₃O₄S₃
M_r	439.87
Crystal system, space group	Monoclinic, Cc
Temperature (K)	120
a, b, c (Å)	14.6659 (7), 9.5498 (6), 13.6720 (7)
β (°)	116.149 (3)
V (Å³)	1718.87 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.64
Crystal size (mm)	0.12 × 0.10 × 0.06

Data collection
Diffractometer	Bruker-Nonius Roper CCD camera on κ-goniostat diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.927, 0.963
No. of measured, independent and observed [I > 2σ(I)] reflections	9021, 3197, 2768
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.098, 1.06
No. of reflections	3197
No. of parameters	239
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.41
Absolute structure	Flack (1983), 1504 Friedel pairs
Absolute structure parameter	0.12 (8)

Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N···O4ⁱ	0.88 (2)	2.21 (4)	2.906 (4)	135 (4)
N2—H1N···O1ⁱⁱ	0.88 (2)	2.59 (4)	3.230 (4)	130 (4)
N3—H3N···O2ⁱⁱⁱ	0.884 (19)	2.11 (3)	2.929 (5)	154 (5)
C10—H10B···O2^iv	0.99	2.31	3.267 (5)	163.4

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x, −y+1, z+1/2; (iii) x, y−1, z; (iv) x+1/2, −y+3/2, z+1/2.

Footnotes

‡Current address: School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, England.

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