Bis(1,2,3-benzotriazolium) sulfate dihydrate.

In the asymmetric unit of the title hydrated salt, 2C6H6N3 (+)·SO4 (2-)·2H2O, there are two independent sulfate ions, one lying on a twofold axis, and the other in a general position. There are three independent benzotriazolium cations and three independent water mol-ecules. The sulfate ion in a general position forms hydrogen-bonded chains of stoichiometry SO4 (2-)·3H2O in the b-axis direction. The sulfate on the twofold axis is unhydrated and accepts hydrogen bonds from four surrounding benzotriazoles. The benzotriazolium cations form two types of stacks along b. One stack contains only one type of independent cation, related by inversion centers. The other stack contains two alternating independent cations and no symmetry. The two types of stacks have orientations which are rotated by about 79° in the ac plane. 12 symmetrically distinct hydrogen bonds of type N-H⋯O(sulfate), N-H⋯O(water), O-H⋯O(sulfate) and O-H⋯O(water), with donor-acceptor distances in the range 2.5490 (13)-2.7871 (12) Å, form a three-dimensional array.

Related literature

For the structure of benzotriazole hydrogensulfate, see: Giordano (1980 ▶); Meléndez et al. (1996 ▶); Ramos-Organillo & Contreras (2007 ▶). For the structure of benzotriazolium dihydrogen phosphate, see: Emsley et al. (1985 ▶) and for the structure of benzotriazolium perchlorate monohydrate, see: Sieroń (2007 ▶). For the preparation and purification of benzotriazole with discussion of impurities, see: Damschroder & Peterson (1955 ▶); Miller & Schlaudecker (1958 ▶); Howard & Popplewell (1967 ▶); Spatz & Evans (1973 ▶). For a purification method for aryl­triazoles as their sulfate salts, see: Belter (2013 ▶).

Experimental

Crystal data

2C6H6N3 +·SO4 2−·2H2O

M = 372.37

Monoclinic,

a = 38.312 (3) Å

b = 6.7621 (10) Å

c = 20.987 (2) Å

β = 113.410 (5)°

V = 4989.5 (10) Å3

Z = 12

Mo Kα radiation

μ = 0.24 mm−1

T = 90 K

0.28 × 0.22 × 0.18 mm

Data collection

Bruker Kappa APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.936, T max = 0.958

33853 measured reflections

9017 independent reflections

7722 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.098

S = 1.03

9017 reflections

375 parameters

30 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.56 e Å−3

Δρmin = −0.46 e Å−3

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: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813007472/zl2540sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007472/zl2540Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813007472/zl2540Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

2C6H6N3+·SO42−·2H2O	F(000) = 2328
Mr = 372.37	Dx = 1.487 Mg m−3
Monoclinic, C2/c	Melting point: 387 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 38.312 (3) Å	Cell parameters from 9903 reflections
b = 6.7621 (10) Å	θ = 3.1–32.5°
c = 20.987 (2) Å	µ = 0.24 mm−1
β = 113.410 (5)°	T = 90 K
V = 4989.5 (10) Å3	Needle fragment, colourless
Z = 12	0.28 × 0.22 × 0.18 mm

Bruker Kappa APEXII DUO CCD diffractometer	9017 independent reflections
Radiation source: fine-focus sealed tube	7722 reflections with I > 2σ(I)
TRIUMPH curved graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 32.6°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −57→58
Tmin = 0.936, Tmax = 0.958	k = −10→8
33853 measured reflections	l = −31→30

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0567P)2 + 2.9928P] where P = (Fo2 + 2Fc2)/3
9017 reflections	(Δ/σ)max = 0.001
375 parameters	Δρmax = 0.56 e Å−3
30 restraints	Δρmin = −0.46 e Å−3

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.

	x	y	z	Uiso*/Ueq
N1	0.67711 (2)	0.46488 (13)	0.46788 (4)	0.01481 (14)
H1N	0.6750 (4)	0.478 (2)	0.5115 (6)	0.018*
N2	0.71156 (2)	0.45131 (13)	0.46877 (4)	0.01585 (15)
N3	0.70747 (2)	0.43361 (12)	0.40372 (4)	0.01438 (14)
H3N	0.7307 (3)	0.423 (2)	0.3965 (7)	0.017*
C1	0.64988 (3)	0.45610 (14)	0.40201 (5)	0.01312 (15)
C2	0.66993 (2)	0.43532 (13)	0.35953 (5)	0.01262 (15)
C3	0.65153 (3)	0.42098 (14)	0.28708 (5)	0.01530 (16)
H3	0.6651	0.4051	0.2581	0.018*
C4	0.61243 (3)	0.43150 (15)	0.26072 (5)	0.01780 (18)
H4	0.5986	0.4238	0.2119	0.021*
C5	0.59194 (3)	0.45342 (15)	0.30363 (5)	0.01893 (18)
H5	0.5650	0.4598	0.2826	0.023*
C6	0.61000 (3)	0.46569 (15)	0.37485 (5)	0.01706 (17)
H6	0.5963	0.4797	0.4037	0.020*
N4	0.56493 (2)	0.74001 (12)	0.53044 (4)	0.01388 (14)
H4N	0.5909 (3)	0.737 (2)	0.5631 (6)	0.017*
N5	0.55857 (2)	0.72941 (13)	0.46390 (4)	0.01556 (15)
N6	0.52140 (2)	0.73277 (13)	0.42951 (4)	0.01439 (14)
H6N	0.5123 (4)	0.720 (2)	0.3812 (6)	0.017*
C7	0.53172 (2)	0.74983 (13)	0.54006 (5)	0.01227 (15)
C8	0.50299 (2)	0.74511 (14)	0.47330 (5)	0.01227 (15)
C9	0.46433 (3)	0.75356 (14)	0.46170 (5)	0.01505 (16)
H9	0.4447	0.7508	0.4163	0.018*
C10	0.45658 (3)	0.76613 (15)	0.52029 (5)	0.01654 (17)
H10	0.4308	0.7714	0.5151	0.020*
C11	0.48569 (3)	0.77145 (15)	0.58815 (5)	0.01650 (17)
H11	0.4788	0.7803	0.6269	0.020*
C12	0.52368 (3)	0.76409 (14)	0.59952 (5)	0.01481 (16)
H12	0.5432	0.7684	0.6449	0.018*
N7	0.62831 (2)	0.09067 (12)	0.71668 (4)	0.01345 (14)
H7N	0.6316 (4)	0.110 (2)	0.6751 (6)	0.016*
N8	0.59310 (2)	0.08433 (13)	0.71241 (4)	0.01494 (15)
N9	0.59523 (2)	0.06704 (12)	0.77634 (4)	0.01462 (14)
H9N	0.5716 (3)	0.057 (2)	0.7817 (7)	0.018*
C13	0.65399 (2)	0.07740 (13)	0.78380 (5)	0.01246 (15)
C14	0.63215 (2)	0.06263 (13)	0.82335 (5)	0.01298 (15)
C15	0.64890 (3)	0.04931 (15)	0.89610 (5)	0.01695 (17)
H15	0.6342	0.0411	0.9233	0.020*
C16	0.68810 (3)	0.04896 (16)	0.92546 (5)	0.01979 (19)
H16	0.7008	0.0398	0.9745	0.024*
C17	0.71011 (3)	0.06174 (16)	0.88508 (5)	0.01946 (19)
H17	0.7371	0.0598	0.9080	0.023*
C18	0.69386 (3)	0.07690 (15)	0.81376 (5)	0.01660 (17)
H18	0.7087	0.0864	0.7867	0.020*
S1	0.667426 (6)	0.69362 (3)	0.616423 (10)	0.01027 (5)
O1	0.67023 (2)	0.85284 (11)	0.57055 (4)	0.01523 (13)
O2	0.700031 (19)	0.69702 (11)	0.68344 (4)	0.01676 (14)
O3	0.66609 (2)	0.50055 (10)	0.58176 (4)	0.01686 (13)
O4	0.632125 (19)	0.71736 (11)	0.62831 (3)	0.01558 (13)
S2	0.5000	0.17120 (5)	0.7500	0.01520 (7)
O5	0.53233 (2)	0.04538 (13)	0.79305 (4)	0.02273 (16)
O6	0.51148 (2)	0.29683 (12)	0.70401 (4)	0.02015 (15)
O1W	0.73087 (2)	0.31970 (12)	0.71948 (4)	0.01937 (14)
H11W	0.7519 (4)	0.323 (2)	0.7544 (7)	0.029*
H12W	0.7236 (4)	0.4369 (19)	0.7109 (8)	0.029*
O2W	0.73056 (2)	0.10807 (13)	0.61293 (5)	0.02518 (17)
H21W	0.7140 (4)	0.019 (2)	0.6024 (9)	0.038*
H22W	0.7300 (5)	0.174 (2)	0.6458 (8)	0.038*
O3W	0.63174 (2)	0.16552 (11)	0.59721 (4)	0.01566 (13)
H31W	0.6424 (4)	0.2700 (19)	0.5942 (8)	0.023*
H32W	0.6421 (4)	0.079 (2)	0.5841 (8)	0.023*

	U11	U22	U33	U12	U13	U23
N1	0.0177 (3)	0.0159 (4)	0.0116 (3)	−0.0010 (3)	0.0067 (3)	−0.0015 (3)
N2	0.0166 (3)	0.0175 (4)	0.0129 (3)	−0.0016 (3)	0.0052 (3)	−0.0011 (3)
N3	0.0143 (3)	0.0165 (4)	0.0127 (3)	−0.0016 (3)	0.0058 (3)	−0.0015 (3)
C1	0.0152 (4)	0.0124 (4)	0.0127 (4)	−0.0003 (3)	0.0066 (3)	−0.0011 (3)
C2	0.0143 (3)	0.0123 (4)	0.0119 (3)	−0.0012 (3)	0.0060 (3)	−0.0009 (3)
C3	0.0203 (4)	0.0142 (4)	0.0113 (4)	−0.0023 (3)	0.0060 (3)	−0.0012 (3)
C4	0.0199 (4)	0.0154 (4)	0.0139 (4)	−0.0018 (3)	0.0023 (3)	−0.0009 (3)
C5	0.0151 (4)	0.0167 (4)	0.0216 (4)	0.0004 (3)	0.0038 (3)	−0.0006 (3)
C6	0.0154 (4)	0.0167 (4)	0.0206 (4)	0.0007 (3)	0.0088 (3)	−0.0010 (3)
N4	0.0120 (3)	0.0156 (4)	0.0133 (3)	0.0006 (3)	0.0043 (3)	0.0002 (3)
N5	0.0150 (3)	0.0170 (4)	0.0146 (3)	0.0007 (3)	0.0059 (3)	0.0004 (3)
N6	0.0144 (3)	0.0162 (4)	0.0121 (3)	0.0008 (3)	0.0048 (3)	0.0004 (3)
C7	0.0122 (3)	0.0110 (4)	0.0128 (4)	0.0002 (3)	0.0041 (3)	−0.0001 (3)
C8	0.0129 (3)	0.0116 (4)	0.0115 (3)	0.0004 (3)	0.0040 (3)	0.0005 (3)
C9	0.0116 (3)	0.0144 (4)	0.0166 (4)	0.0003 (3)	0.0028 (3)	0.0011 (3)
C10	0.0137 (4)	0.0151 (4)	0.0217 (4)	0.0013 (3)	0.0079 (3)	0.0014 (3)
C11	0.0187 (4)	0.0156 (4)	0.0176 (4)	0.0009 (3)	0.0097 (3)	0.0003 (3)
C12	0.0166 (4)	0.0151 (4)	0.0122 (4)	0.0002 (3)	0.0051 (3)	−0.0003 (3)
N7	0.0130 (3)	0.0153 (3)	0.0124 (3)	−0.0001 (3)	0.0054 (3)	−0.0010 (3)
N8	0.0131 (3)	0.0168 (4)	0.0147 (3)	−0.0005 (3)	0.0054 (3)	−0.0018 (3)
N9	0.0136 (3)	0.0164 (4)	0.0150 (3)	0.0004 (3)	0.0069 (3)	−0.0006 (3)
C13	0.0128 (3)	0.0119 (4)	0.0128 (4)	0.0004 (3)	0.0051 (3)	−0.0006 (3)
C14	0.0140 (3)	0.0124 (4)	0.0131 (4)	0.0008 (3)	0.0061 (3)	−0.0007 (3)
C15	0.0233 (4)	0.0153 (4)	0.0134 (4)	0.0022 (3)	0.0086 (3)	0.0006 (3)
C16	0.0242 (4)	0.0175 (4)	0.0135 (4)	0.0027 (4)	0.0030 (3)	0.0011 (3)
C17	0.0151 (4)	0.0194 (4)	0.0190 (4)	0.0013 (3)	0.0015 (3)	0.0011 (3)
C18	0.0132 (4)	0.0180 (4)	0.0180 (4)	0.0007 (3)	0.0056 (3)	0.0003 (3)
S1	0.01024 (9)	0.01164 (10)	0.00885 (9)	−0.00031 (6)	0.00372 (7)	−0.00058 (7)
O1	0.0187 (3)	0.0137 (3)	0.0150 (3)	−0.0005 (2)	0.0085 (2)	0.0023 (2)
O2	0.0125 (3)	0.0202 (3)	0.0128 (3)	−0.0007 (2)	−0.0001 (2)	−0.0005 (2)
O3	0.0262 (3)	0.0126 (3)	0.0154 (3)	−0.0030 (3)	0.0120 (3)	−0.0030 (2)
O4	0.0120 (3)	0.0237 (4)	0.0123 (3)	0.0019 (2)	0.0062 (2)	0.0018 (2)
S2	0.01142 (12)	0.02288 (16)	0.01203 (13)	0.000	0.00544 (10)	0.000
O5	0.0154 (3)	0.0314 (4)	0.0247 (4)	0.0064 (3)	0.0115 (3)	0.0105 (3)
O6	0.0196 (3)	0.0289 (4)	0.0114 (3)	−0.0045 (3)	0.0055 (3)	0.0018 (3)
O1W	0.0163 (3)	0.0192 (3)	0.0177 (3)	0.0024 (3)	0.0016 (3)	0.0022 (3)
O2W	0.0202 (3)	0.0281 (4)	0.0335 (4)	−0.0091 (3)	0.0172 (3)	−0.0119 (3)
O3W	0.0173 (3)	0.0141 (3)	0.0177 (3)	−0.0001 (2)	0.0092 (3)	0.0004 (2)

N1—N2	1.3159 (11)	C12—H12	0.9500
N1—C1	1.3626 (12)	N7—N8	1.3167 (11)
N1—H1N	0.955 (11)	N7—C13	1.3634 (11)
N2—N3	1.3162 (11)	N7—H7N	0.940 (11)
N3—C2	1.3671 (11)	N8—N9	1.3167 (11)
N3—H3N	0.963 (11)	N9—C14	1.3661 (11)
C1—C2	1.3959 (12)	N9—H9N	0.956 (11)
C1—C6	1.4044 (13)	C13—C14	1.3969 (12)
C2—C3	1.4023 (12)	C13—C18	1.4017 (12)
C3—C4	1.3772 (13)	C14—C15	1.4044 (13)
C3—H3	0.9500	C15—C16	1.3781 (14)
C4—C5	1.4183 (15)	C15—H15	0.9500
C4—H4	0.9500	C16—C17	1.4158 (15)
C5—C6	1.3775 (14)	C16—H16	0.9500
C5—H5	0.9500	C17—C18	1.3777 (14)
C6—H6	0.9500	C17—H17	0.9500
N4—N5	1.3207 (11)	C18—H18	0.9500
N4—C7	1.3668 (11)	S1—O2	1.4639 (7)
N4—H4N	0.959 (11)	S1—O1	1.4765 (7)
N5—N6	1.3163 (11)	S1—O4	1.4783 (7)
N6—C8	1.3652 (12)	S1—O3	1.4855 (7)
N6—H6N	0.935 (11)	S2—O6i	1.4779 (8)
C7—C8	1.3965 (12)	S2—O6	1.4779 (8)
C7—C12	1.4024 (13)	S2—O5	1.4783 (8)
C8—C9	1.4036 (12)	S2—O5i	1.4783 (8)
C9—C10	1.3775 (14)	O1W—H11W	0.846 (12)
C9—H9	0.9500	O1W—H12W	0.835 (12)
C10—C11	1.4181 (14)	O2W—H21W	0.841 (13)
C10—H10	0.9500	O2W—H22W	0.830 (13)
C11—C12	1.3792 (13)	O3W—H31W	0.830 (12)
C11—H11	0.9500	O3W—H32W	0.812 (12)
N2—N1—C1	111.75 (8)	C12—C11—H11	119.1
N2—N1—H1N	117.3 (8)	C10—C11—H11	119.1
C1—N1—H1N	130.9 (8)	C11—C12—C7	115.99 (8)
N1—N2—N3	106.63 (7)	C11—C12—H12	122.0
N2—N3—C2	111.26 (8)	C7—C12—H12	122.0
N2—N3—H3N	115.7 (8)	N8—N7—C13	111.56 (8)
C2—N3—H3N	133.0 (8)	N8—N7—H7N	117.0 (8)
N1—C1—C2	104.99 (8)	C13—N7—H7N	131.3 (8)
N1—C1—C6	132.90 (9)	N7—N8—N9	106.65 (7)
C2—C1—C6	122.10 (8)	N8—N9—C14	111.41 (8)
N3—C2—C1	105.37 (8)	N8—N9—H9N	116.6 (8)
N3—C2—C3	132.46 (9)	C14—N9—H9N	132.0 (8)
C1—C2—C3	122.17 (8)	N7—C13—C14	105.18 (8)
C4—C3—C2	115.46 (9)	N7—C13—C18	132.38 (9)
C4—C3—H3	122.3	C14—C13—C18	122.44 (8)
C2—C3—H3	122.3	N9—C14—C13	105.20 (8)
C3—C4—C5	122.59 (9)	N9—C14—C15	132.95 (9)
C3—C4—H4	118.7	C13—C14—C15	121.85 (8)
C5—C4—H4	118.7	C16—C15—C14	115.62 (9)
C6—C5—C4	121.94 (9)	C16—C15—H15	122.2
C6—C5—H5	119.0	C14—C15—H15	122.2
C4—C5—H5	119.0	C15—C16—C17	122.32 (9)
C5—C6—C1	115.73 (9)	C15—C16—H16	118.8
C5—C6—H6	122.1	C17—C16—H16	118.8
C1—C6—H6	122.1	C18—C17—C16	122.35 (9)
N5—N4—C7	111.54 (7)	C18—C17—H17	118.8
N5—N4—H4N	117.3 (8)	C16—C17—H17	118.8
C7—N4—H4N	131.2 (8)	C17—C18—C13	115.42 (9)
N6—N5—N4	106.49 (8)	C17—C18—H18	122.3
N5—N6—C8	111.57 (8)	C13—C18—H18	122.3
N5—N6—H6N	116.7 (9)	O2—S1—O1	111.08 (4)
C8—N6—H6N	131.6 (9)	O2—S1—O4	108.95 (4)
N4—C7—C8	105.05 (8)	O1—S1—O4	109.84 (4)
N4—C7—C12	132.93 (8)	O2—S1—O3	109.54 (4)
C8—C7—C12	122.02 (8)	O1—S1—O3	108.59 (4)
N6—C8—C7	105.35 (8)	O4—S1—O3	108.81 (4)
N6—C8—C9	132.65 (8)	O6i—S2—O6	109.83 (7)
C7—C8—C9	122.00 (8)	O6i—S2—O5	109.04 (4)
C10—C9—C8	115.75 (8)	O6—S2—O5	109.60 (4)
C10—C9—H9	122.1	O6i—S2—O5i	109.60 (4)
C8—C9—H9	122.1	O6—S2—O5i	109.04 (4)
C9—C10—C11	122.39 (8)	O5—S2—O5i	109.73 (7)
C9—C10—H10	118.8	H11W—O1W—H12W	106.4 (15)
C11—C10—H10	118.8	H21W—O2W—H22W	109.9 (17)
C12—C11—C10	121.84 (9)	H31W—O3W—H32W	105.2 (15)
C1—N1—N2—N3	0.04 (11)	C12—C7—C8—C9	−0.26 (14)
N1—N2—N3—C2	−0.07 (11)	N6—C8—C9—C10	−179.81 (10)
N2—N1—C1—C2	0.01 (11)	C7—C8—C9—C10	−0.20 (13)
N2—N1—C1—C6	−179.36 (10)	C8—C9—C10—C11	0.36 (14)
N2—N3—C2—C1	0.07 (11)	C9—C10—C11—C12	−0.07 (15)
N2—N3—C2—C3	−179.97 (10)	C10—C11—C12—C7	−0.38 (14)
N1—C1—C2—N3	−0.05 (10)	N4—C7—C12—C11	179.76 (10)
C6—C1—C2—N3	179.41 (9)	C8—C7—C12—C11	0.54 (14)
N1—C1—C2—C3	179.99 (9)	C13—N7—N8—N9	0.04 (10)
C6—C1—C2—C3	−0.56 (14)	N7—N8—N9—C14	0.23 (10)
N3—C2—C3—C4	−179.11 (10)	N8—N7—C13—C14	−0.28 (10)
C1—C2—C3—C4	0.84 (14)	N8—N7—C13—C18	179.76 (10)
C2—C3—C4—C5	−0.58 (14)	N8—N9—C14—C13	−0.40 (10)
C3—C4—C5—C6	0.02 (16)	N8—N9—C14—C15	178.88 (10)
C4—C5—C6—C1	0.31 (15)	N7—C13—C14—N9	0.39 (10)
N1—C1—C6—C5	179.24 (10)	C18—C13—C14—N9	−179.64 (9)
C2—C1—C6—C5	−0.04 (14)	N7—C13—C14—C15	−178.98 (9)
C7—N4—N5—N6	0.19 (11)	C18—C13—C14—C15	0.98 (15)
N4—N5—N6—C8	−0.16 (11)	N9—C14—C15—C16	179.94 (10)
N5—N4—C7—C8	−0.14 (10)	C13—C14—C15—C16	−0.89 (14)
N5—N4—C7—C12	−179.45 (10)	C14—C15—C16—C17	0.17 (15)
N5—N6—C8—C7	0.08 (11)	C15—C16—C17—C18	0.50 (17)
N5—N6—C8—C9	179.73 (10)	C16—C17—C18—C13	−0.44 (15)
N4—C7—C8—N6	0.03 (10)	N7—C13—C18—C17	179.67 (10)
C12—C7—C8—N6	179.44 (9)	C14—C13—C18—C17	−0.29 (14)
N4—C7—C8—C9	−179.67 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3	0.96 (1)	1.65 (1)	2.5981 (11)	173 (1)
N3—H3N···O2Wii	0.96 (1)	1.59 (1)	2.5492 (11)	176 (1)
N4—H4N···O4	0.96 (1)	1.63 (1)	2.5822 (10)	170 (1)
N6—H6N···O6iii	0.94 (1)	1.66 (1)	2.5834 (11)	170 (1)
N7—H7N···O3W	0.94 (1)	1.68 (1)	2.6119 (11)	172 (1)
N9—H9N···O5	0.96 (1)	1.62 (1)	2.5735 (11)	178 (1)
O1W—H11W···O2iv	0.85 (1)	1.98 (1)	2.7498 (10)	151 (2)
O1W—H12W···O2	0.84 (1)	1.96 (1)	2.7871 (11)	172 (2)
O2W—H21W···O1v	0.84 (1)	1.90 (1)	2.7345 (11)	170 (2)
O2W—H22W···O1W	0.83 (1)	1.82 (1)	2.6507 (12)	178 (2)
O3W—H31W···O3	0.83 (1)	1.87 (1)	2.7034 (10)	176 (2)
O3W—H32W···O1v	0.81 (1)	1.96 (1)	2.7594 (11)	169 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3	0.96 (1)	1.65 (1)	2.5981 (11)	173 (1)
N3—H3N⋯O2W i	0.96 (1)	1.59 (1)	2.5492 (11)	176 (1)
N4—H4N⋯O4	0.96 (1)	1.63 (1)	2.5822 (10)	170 (1)
N6—H6N⋯O6ii	0.94 (1)	1.66 (1)	2.5834 (11)	170 (1)
N7—H7N⋯O3W	0.94 (1)	1.68 (1)	2.6119 (11)	172 (1)
N9—H9N⋯O5	0.96 (1)	1.62 (1)	2.5735 (11)	178 (1)
O1W—H11W⋯O2iii	0.85 (1)	1.98 (1)	2.7498 (10)	151 (2)
O1W—H12W⋯O2	0.84 (1)	1.96 (1)	2.7871 (11)	172 (2)
O2W—H21W⋯O1iv	0.84 (1)	1.90 (1)	2.7345 (11)	170 (2)
O2W—H22W⋯O1W	0.83 (1)	1.82 (1)	2.6507 (12)	178 (2)
O3W—H31W⋯O3	0.83 (1)	1.87 (1)	2.7034 (10)	176 (2)
O3W—H32W⋯O1iv	0.81 (1)	1.96 (1)	2.7594 (11)	169 (2)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .