Hydro­chloro­thia­zide–aniline (1/1)

Johnston, A.; Florence, A.J.; Kennedy, A.R.

doi:10.1107/S1600536805021914

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 61| Part 8| August 2005| Pages o2520-o2522

https://doi.org/10.1107/S1600536805021914

Hydrochlorothiazide–aniline (1/1)

Andrea Johnston,^a Alastair J. Florence ^a ^* and Alan R. Kennedy ^b

^aDepartment of Pharmaceutical Sciences, University of Strathclyde, 27 Taylor Street, Glasgow G4 0NR, Scotland, and ^bWestCHEM, Department of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland
^*Correspondence e-mail: alastair.florence@strath.ac.uk

(Received 23 June 2005; accepted 7 July 2005; online 13 July 2005)

Hydrochlorothiazide forms a 1:1 solvate with aniline, C₇H₈ClN₃O₄S₂·C₆H₇N. The crystal structure contains a hydrogen-bonding network comprising two N—H⋯N and three N—H⋯O contacts.

Comment

Hydrochlorothiazide (HCT) is a thiazide diuretic which is known to crystallize in at least one non-solvated form (Dupont & Dideberg, 1972 ). The aniline solvate, (I), was produced during an automated parallel crystallization polymorph screen on HCT. The sample was identified as a novel form using multisample X-ray powder diffraction analysis of all recrystallized samples (Florence et al., 2003 ). Subsequent manual recrystallization from a saturated 1:1 acetone–aniline solution by slow evaporation at 278 K yielded samples of (I) suitable for single-crystal X-ray analysis (Fig. 1).

In (I), the N1—S1—C1—N2—C2—C7 six-membered ring in HCT adopts a non-planar conformation, with atoms S1 and N1 having deviations of 0.271 (1) and 0.843 (1) Å, respectively, from the least-squares plane through atoms C2–C7. The sulfonamide side chain adopts a torsion angle N3—S2—C5—C4 of 69.05 (12)°, such that atom O4 eclipses H6 and atoms O3 and N3 are staggered with respect to Cl1. In the non-solvated structure (Dupont & Dideberg, 1972), this group is rotated by approximately 130° compared to (I) such that the amine group lies on the opposite side of the benzothiadiazine moiety. The aniline molecule is planar, the greatest deviation of any non-H atom from the least-squares plane through C8–C13/N4 being 0.013 (1) Å for C8.

The crystal structure is stabilized by a network of hydrogen bonds interconnecting (a) HCT molecules (Fig. 2, contacts 1 and 2) and (b) HCT and solvent molecules (contacts 3, 4 and 5). Two C—H⋯O contacts also exist between HCT molecules (contacts 6 and 7). Contact 1 (N3—H3N⋯O2) forms a centrosymmetric R₂²(16) motif between molecules of HCT, whilst contacts 4 and 5 (N4—H5N⋯N3 and N4—H6N⋯O4) combine to form an R₄⁴(12) motif between aniline and HCT (Fig. 3). Hydrophobic interactions between HCT and aniline include a C—H⋯π contact and an offset face-to-face (off) π–π approach (Fig. 4).

Figure 1
Plot of the asymmetric unit contents with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

Figure 2
A packing diagram of (I)

. Dashed lines indicate hydrogen bonds and unique contacts are labelled as follows: 1 = N3⋯O2 [2.9725 (16) Å, O2 in the molecule at (1 − x, 1 − y, 2 − z)]; 2 = N3⋯O1 [2.9390 (15) Å, O1 in the molecule at ( $[{1\over 2}]$ + x, $[{1\over 2}]$ − y, − $[{1\over 2}]$ + z)]; 3 = N1⋯N4 [2.9652 (17) Å]; 4 = N4⋯N3 [3.3944 (18) Å, in the molecule at (−1 + x, y, z)]; 5 = N4⋯O4 [3.1000 (17) Å, O4 in the molecule at (1 − x, 1 − y, 2 − z)]; 6 = C1⋯O3 [3.2535 (18) Å, O3 in the molecule at (1 − x, −y, 2 − z)]; 7 = C1⋯O3 [3.2852 (17) Å, O3 in the molecule at (−1 + x, y, z)]. Contacts calculated and illustrated using PLATON (Spek, 2003

; program version 280604)

Figure 3
The R₂²(16) (left) and R₄⁴(12) hydrogen-bond motifs in the crystal structure of (I)

Figure 4
Hydrophobic interactions in (I)

, showing a C3—H3⋯centroid contact to the centroid of the benzene ring of aniline [C3⋯centroid = 3.618 (2) Å] (top) and a π–π off-stacking interaction between HCT and aniline with a centroid–centroid distance of 3.6955 (8) Å (bottom). Contacts are illustrated using dashed lines.

Experimental

A single-crystal sample of the title compound was recrystallized from a 1:1 acetone–aniline solution by slow evaporation at 278 K.

Crystal data

C₇H₈ClN₃O₄S₂·C₆H₇N
M_r = 390.86
Monoclinic, P 2₁ /n
a = 9.7757 (3) Å
b = 10.5004 (3) Å
c = 15.6093 (4) Å
β = 91.692 (2)°
V = 1601.58 (8) Å³
Z = 4
D_x = 1.621 Mg m⁻³
Mo Kα radiation
Cell parameters from 5824 reflections
θ = 1.0–32.0°
μ = 0.53 mm⁻¹
T = 123 (2) K
Prism, colourless
0.38 × 0.30 × 0.18 mm

Data collection

Nonius KappaCCD diffractometer
ω and φ scans
Absorption correction: none
10766 measured reflections
5573 independent reflections
4379 reflections with I > 2σ(I)
R_int = 0.027
θ_max = 32.0°
h = −14 → 14
k = −15 → 15
l = −23 → 23

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.084
S = 1.02
5573 reflections
241 parameters
H atoms treated by a mixture of independent and constrained refinement
w = 1/[σ²(F_o²) + (0.036P)² + 0.781P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.002
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N4	0.87 (2)	2.10 (2)	2.9652 (17)	174 (2)
N3—H3N⋯O2ⁱ	0.85 (2)	2.13 (2)	2.9725 (16)	169 (2)
N3—H4N⋯O1ⁱⁱ	0.90 (2)	2.09 (2)	2.9390 (15)	157 (2)
N4—H5N⋯N3ⁱⁱⁱ	0.89 (2)	2.52 (2)	3.3944 (18)	169 (2)
N4—H6N⋯O4ⁱ	0.83 (2)	2.28 (2)	3.1000 (17)	173 (2)
C1—H1A⋯O3^iv	0.99	2.37	3.2535 (18)	148
C1—H1B⋯O3ⁱⁱⁱ	0.99	2.47	3.2852 (17)	139
C6—H6⋯O4	0.95	2.38	2.8101 (16)	107
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) x-1, y, z; (iv) -x+1, -y, -z+2.

The N-bound H atoms were found in difference maps and refined freely [N—H = 0.77 (2)–0.90 (2) Å]. The remaining H atoms were positioned geometrically at distances of 0.95 (CH) and 0.99 Å (CH₂) from the parent C atoms; a riding model was used [U_iso(H) = 1.2U_eq(C)] during the refinement process.

Data collection: COLLECT (Hooft, 1988 ) and DENZO (Otwinowski & Minor, 1997 ); cell refinement: DENZO and COLLECT; data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536805021914/hk6025sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536805021914/hk6025Isup2.hkl

Computing details top

Data collection: COLLECT (Hooft, 1988) and DENZO (Otwinowski & Minor, 1997); cell refinement: DENZO and COLLECT; data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Hydrochlorothiazide–aniline (1/1) top

Crystal data top

C₇H₈ClN₃O₄S₂·C₆H₇N	F(000) = 808
M_r = 390.86	D_x = 1.621 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5824 reflections
a = 9.7757 (3) Å	θ = 1.0–32.0°
b = 10.5004 (3) Å	µ = 0.53 mm⁻¹
c = 15.6093 (4) Å	T = 123 K
β = 91.692 (2)°	Prism, colourless
V = 1601.58 (8) Å³	0.38 × 0.30 × 0.18 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	4379 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.027
Graphite monochromator	θ_max = 32.0°, θ_min = 2.3°
ω and φ scans	h = −14→14
10766 measured reflections	k = −15→15
5573 independent reflections	l = −23→23

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.036P)² + 0.781P] where P = (F_o² + 2F_c²)/3
5573 reflections	(Δ/σ)_max = 0.002
241 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.53 e Å⁻³

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	0.60656 (4)	0.10198 (3)	0.76024 (2)	0.02108 (8)
S1	0.31003 (3)	0.26967 (3)	1.08865 (2)	0.01544 (7)
S2	0.77750 (3)	0.24797 (3)	0.91533 (2)	0.01472 (7)
O1	0.32719 (11)	0.18921 (11)	1.16255 (6)	0.0239 (2)
O2	0.34691 (11)	0.40187 (10)	1.09743 (7)	0.0236 (2)
O3	0.85848 (10)	0.14419 (10)	0.88491 (6)	0.0208 (2)
O4	0.81363 (10)	0.30354 (10)	0.99740 (6)	0.0201 (2)
N1	0.15186 (12)	0.26228 (12)	1.05407 (7)	0.0174 (2)
N2	0.19235 (13)	0.10009 (12)	0.94740 (8)	0.0197 (2)
N3	0.78744 (12)	0.36009 (12)	0.84548 (7)	0.0169 (2)
N4	0.10950 (14)	0.44391 (13)	0.91027 (8)	0.0213 (2)
C1	0.11769 (14)	0.13361 (14)	1.02355 (9)	0.0186 (3)
H1A	0.1397	0.0714	1.0696	0.022*
H1B	0.0182	0.1286	1.0103	0.022*
C2	0.32626 (13)	0.13305 (13)	0.93952 (8)	0.0154 (2)
C3	0.39693 (14)	0.10032 (13)	0.86510 (8)	0.0168 (2)
H3	0.3510	0.0541	0.8205	0.020*
C4	0.53177 (14)	0.13466 (12)	0.85650 (8)	0.0153 (2)
C5	0.60499 (13)	0.19994 (12)	0.92215 (8)	0.0144 (2)
C6	0.53557 (13)	0.23532 (13)	0.99458 (8)	0.0145 (2)
H6	0.5823	0.2815	1.0389	0.017*
C7	0.39858 (13)	0.20412 (12)	1.00318 (8)	0.0143 (2)
C8	0.19792 (14)	0.41456 (13)	0.84290 (8)	0.0176 (3)
C9	0.15625 (15)	0.33026 (14)	0.77775 (9)	0.0210 (3)
H9	0.0674	0.2936	0.7780	0.025*
C10	0.24467 (17)	0.30030 (15)	0.71291 (9)	0.0253 (3)
H10	0.2160	0.2423	0.6693	0.030*
C11	0.37402 (17)	0.35352 (16)	0.71078 (10)	0.0266 (3)
H11	0.4332	0.3336	0.6655	0.032*
C12	0.41639 (16)	0.43643 (16)	0.77571 (10)	0.0264 (3)
H12	0.5049	0.4736	0.7748	0.032*
C13	0.32954 (15)	0.46523 (14)	0.84205 (10)	0.0219 (3)
H13	0.3603	0.5199	0.8871	0.026*
H1N	0.1400 (19)	0.3198 (19)	1.0149 (12)	0.028 (5)*
H2N	0.152 (2)	0.076 (2)	0.9075 (13)	0.034 (5)*
H3N	0.740 (2)	0.426 (2)	0.8565 (13)	0.038 (6)*
H4N	0.777 (2)	0.334 (2)	0.7909 (13)	0.036 (5)*
H5N	0.023 (2)	0.434 (2)	0.8934 (13)	0.039 (6)*
H6N	0.126 (2)	0.515 (2)	0.9315 (12)	0.030 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.02599 (17)	0.02251 (16)	0.01513 (14)	−0.00209 (13)	0.00727 (11)	−0.00585 (12)
S1	0.01651 (15)	0.01855 (15)	0.01136 (13)	0.00149 (12)	0.00224 (10)	−0.00156 (11)
S2	0.01443 (14)	0.01536 (15)	0.01445 (14)	0.00048 (12)	0.00169 (10)	0.00067 (11)
O1	0.0255 (5)	0.0336 (6)	0.0129 (4)	0.0078 (5)	0.0032 (4)	0.0041 (4)
O2	0.0244 (5)	0.0211 (5)	0.0255 (5)	−0.0013 (4)	0.0048 (4)	−0.0089 (4)
O3	0.0187 (5)	0.0184 (5)	0.0254 (5)	0.0046 (4)	0.0034 (4)	0.0008 (4)
O4	0.0185 (5)	0.0260 (5)	0.0157 (4)	−0.0035 (4)	−0.0012 (4)	−0.0012 (4)
N1	0.0160 (5)	0.0192 (6)	0.0169 (5)	0.0017 (4)	0.0012 (4)	0.0015 (4)
N2	0.0194 (6)	0.0228 (6)	0.0168 (5)	−0.0055 (5)	0.0021 (4)	−0.0043 (5)
N3	0.0201 (6)	0.0151 (5)	0.0157 (5)	0.0008 (4)	0.0045 (4)	0.0015 (4)
N4	0.0229 (6)	0.0213 (6)	0.0196 (6)	0.0003 (5)	0.0012 (5)	0.0001 (5)
C1	0.0182 (6)	0.0193 (6)	0.0186 (6)	−0.0012 (5)	0.0041 (5)	0.0011 (5)
C2	0.0180 (6)	0.0133 (6)	0.0149 (5)	−0.0024 (5)	0.0016 (4)	0.0001 (4)
C3	0.0206 (6)	0.0154 (6)	0.0143 (5)	−0.0034 (5)	0.0017 (5)	−0.0026 (5)
C4	0.0207 (6)	0.0129 (6)	0.0125 (5)	−0.0001 (5)	0.0039 (4)	−0.0014 (4)
C5	0.0155 (6)	0.0141 (6)	0.0136 (5)	−0.0002 (5)	0.0019 (4)	0.0002 (4)
C6	0.0162 (6)	0.0162 (6)	0.0111 (5)	−0.0002 (5)	−0.0002 (4)	−0.0004 (4)
C7	0.0173 (6)	0.0143 (6)	0.0112 (5)	0.0005 (5)	0.0023 (4)	−0.0002 (4)
C8	0.0203 (6)	0.0159 (6)	0.0167 (6)	0.0015 (5)	−0.0016 (5)	0.0034 (5)
C9	0.0232 (7)	0.0188 (7)	0.0208 (6)	−0.0025 (5)	−0.0042 (5)	0.0024 (5)
C10	0.0357 (8)	0.0218 (7)	0.0183 (6)	0.0040 (6)	−0.0042 (6)	−0.0014 (5)
C11	0.0306 (8)	0.0283 (8)	0.0213 (7)	0.0092 (7)	0.0045 (6)	0.0064 (6)
C12	0.0205 (7)	0.0266 (8)	0.0320 (8)	0.0001 (6)	0.0010 (6)	0.0064 (6)
C13	0.0221 (7)	0.0184 (6)	0.0250 (7)	−0.0020 (5)	−0.0037 (5)	0.0001 (5)

Geometric parameters (Å, º) top

Cl1—C4	1.7248 (13)	C1—H1B	0.9900
S1—O1	1.4357 (10)	C2—C3	1.4114 (18)
S1—O2	1.4398 (11)	C2—C7	1.4151 (18)
S1—N1	1.6244 (12)	C3—C4	1.3769 (19)
S1—C7	1.7524 (13)	C3—H3	0.9500
S2—O3	1.4359 (10)	C4—C5	1.4103 (18)
S2—O4	1.4421 (10)	C5—C6	1.3864 (17)
S2—N3	1.6095 (12)	C6—C7	1.3890 (18)
S2—C5	1.7665 (13)	C6—H6	0.9500
N1—C1	1.4678 (18)	C8—C13	1.393 (2)
N1—H1N	0.86 (2)	C8—C9	1.3997 (19)
N2—C2	1.3631 (18)	C9—C10	1.386 (2)
N2—C1	1.4564 (17)	C9—H9	0.9500
N2—H2N	0.77 (2)	C10—C11	1.384 (2)
N3—H3N	0.85 (2)	C10—H10	0.9500
N3—H4N	0.90 (2)	C11—C12	1.390 (2)
N4—C8	1.4148 (18)	C11—H11	0.9500
N4—H5N	0.89 (2)	C12—C13	1.392 (2)
N4—H6N	0.83 (2)	C12—H12	0.9500
C1—H1A	0.9900	C13—H13	0.9500

O1—S1—O2	117.90 (7)	C4—C3—C2	120.64 (12)
O1—S1—N1	109.05 (6)	C4—C3—H3	119.7
O2—S1—N1	108.12 (6)	C2—C3—H3	119.7
O1—S1—C7	109.38 (6)	C3—C4—C5	121.55 (12)
O2—S1—C7	108.86 (6)	C3—C4—Cl1	117.67 (10)
N1—S1—C7	102.42 (6)	C5—C4—Cl1	120.70 (10)
O3—S2—O4	118.55 (6)	C6—C5—C4	118.21 (12)
O3—S2—N3	106.63 (6)	C6—C5—S2	117.63 (10)
O4—S2—N3	106.73 (6)	C4—C5—S2	124.05 (10)
O3—S2—C5	109.87 (6)	C5—C6—C7	120.81 (12)
O4—S2—C5	105.74 (6)	C5—C6—H6	119.6
N3—S2—C5	109.06 (6)	C7—C6—H6	119.6
C1—N1—S1	110.92 (9)	C6—C7—C2	121.30 (11)
C1—N1—H1N	112.9 (13)	C6—C7—S1	118.70 (10)
S1—N1—H1N	107.9 (13)	C2—C7—S1	119.60 (10)
C2—N2—C1	121.20 (12)	C13—C8—C9	118.93 (13)
C2—N2—H2N	118.6 (15)	C13—C8—N4	120.58 (13)
C1—N2—H2N	119.0 (15)	C9—C8—N4	120.44 (13)
S2—N3—H3N	114.2 (14)	C10—C9—C8	119.97 (14)
S2—N3—H4N	114.1 (13)	C10—C9—H9	120.0
H3N—N3—H4N	113.3 (19)	C8—C9—H9	120.0
C8—N4—H5N	110.7 (13)	C11—C10—C9	121.05 (14)
C8—N4—H6N	112.1 (14)	C11—C10—H10	119.5
H5N—N4—H6N	113.4 (19)	C9—C10—H10	119.5
N2—C1—N1	111.88 (11)	C10—C11—C12	119.23 (14)
N2—C1—H1A	109.2	C10—C11—H11	120.4
N1—C1—H1A	109.2	C12—C11—H11	120.4
N2—C1—H1B	109.2	C11—C12—C13	120.23 (14)
N1—C1—H1B	109.2	C11—C12—H12	119.9
H1A—C1—H1B	107.9	C13—C12—H12	119.9
N2—C2—C3	120.47 (12)	C12—C13—C8	120.54 (14)
N2—C2—C7	122.12 (12)	C12—C13—H13	119.7
C3—C2—C7	117.38 (12)	C8—C13—H13	119.7

O1—S1—N1—C1	−64.70 (10)	S2—C5—C6—C7	178.11 (10)
O2—S1—N1—C1	165.97 (9)	C5—C6—C7—C2	1.4 (2)
C7—S1—N1—C1	51.12 (10)	C5—C6—C7—S1	−171.34 (10)
C2—N2—C1—N1	40.07 (18)	N2—C2—C7—C6	179.10 (13)
S1—N1—C1—N2	−66.52 (13)	C3—C2—C7—C6	−2.93 (19)
C1—N2—C2—C3	−179.71 (13)	N2—C2—C7—S1	−8.21 (18)
C1—N2—C2—C7	−1.8 (2)	C3—C2—C7—S1	169.76 (10)
N2—C2—C3—C4	179.28 (13)	O1—S1—C7—C6	−87.71 (12)
C7—C2—C3—C4	1.3 (2)	O2—S1—C7—C6	42.40 (12)
C2—C3—C4—C5	1.9 (2)	N1—S1—C7—C6	156.72 (11)
C2—C3—C4—Cl1	−175.03 (10)	O1—S1—C7—C2	99.41 (11)
C3—C4—C5—C6	−3.4 (2)	O2—S1—C7—C2	−130.48 (11)
Cl1—C4—C5—C6	173.40 (10)	N1—S1—C7—C2	−16.17 (12)
C3—C4—C5—S2	−179.53 (11)	C13—C8—C9—C10	−1.2 (2)
Cl1—C4—C5—S2	−2.69 (17)	N4—C8—C9—C10	−178.78 (13)
O3—S2—C5—C6	136.39 (11)	C8—C9—C10—C11	−0.7 (2)
O4—S2—C5—C6	7.36 (12)	C9—C10—C11—C12	1.2 (2)
N3—S2—C5—C6	−107.07 (11)	C10—C11—C12—C13	0.1 (2)
O3—S2—C5—C4	−47.49 (13)	C11—C12—C13—C8	−2.0 (2)
O4—S2—C5—C4	−176.52 (11)	C9—C8—C13—C12	2.5 (2)
N3—S2—C5—C4	69.04 (13)	N4—C8—C13—C12	−179.93 (13)
C4—C5—C6—C7	1.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N4	0.865 (19)	2.104 (19)	2.9652 (17)	174.0 (18)
N3—H3N···O2ⁱ	0.85 (2)	2.13 (2)	2.9725 (16)	168.6 (18)
N3—H4N···O1ⁱⁱ	0.90 (2)	2.09 (2)	2.9390 (15)	157.1 (17)
N4—H5N···N3ⁱⁱⁱ	0.89 (2)	2.52 (2)	3.3944 (18)	168.6 (18)
N4—H6N···O4ⁱ	0.83 (2)	2.28 (2)	3.1000 (17)	173.1 (17)
C1—H1A···O3^iv	0.99	2.37	3.2535 (18)	148
C1—H1B···O3ⁱⁱⁱ	0.99	2.47	3.2852 (17)	139
C6—H6···O4	0.95	2.38	2.8101 (16)	107

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

Acknowledgements

The authors thank the Basic Technology programme of the UK Research Councils for funding this work under the project Control and Prediction of the Organic Solid State (URL: www.cposs.org.uk).

References

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