Bosentan monohydrate.

In the title compound, C27H29N5O6S·H2O {systematic name: 4-tert-butyl-N-[6-(2-hy-droxy-eth-oxy)-5-(2-meth-oxy-phen-oxy)-2-(pyrimidin-2-yl)pyrimidin-4-yl]benzene-1-sulfonamide monohydrate], the dihedral angle between the mean planes of the pyrimidine rings is 27.0 (1)°. The dihedral angle between the mean planes of the benzene rings is 47.7 (8)°, forming a U-shaped channel around the chain of twisted pyrimidine rings. The crystal packing is stabilized by O-H⋯O, O-H⋯N and N-H⋯O hydrogen bonds with a single water mol-ecule, and weak O-H⋯N inter-molecular inter-actions between the hy-droxy group and one of the pyrimidine rings producing an two-dimensional supra-molecular array in the bc plane. The title compound studied was a merohedral twin with the major component being approximately 57%.

Related literature

For reviews of bosentan in the management of pulmonary arterial hypertension and systemic sclerosis, see: Gabbay et al. (2007 ▶); Kumar et al. (2011 ▶); Oldfield & Lyseng-Williamson (2006 ▶). For related structures, see: Singh et al. (1985 ▶); El-Ghamry et al. (2008 ▶); Kant et al. (2012 ▶).

Experimental

Crystal data

C27H29N5O6S·H2O

M = 569.63

Monoclinic,

a = 12.3393 (4) Å

b = 15.1238 (6) Å

c = 14.6988 (4) Å

β = 95.037 (3)°

V = 2732.46 (16) Å3

Z = 4

Cu Kα radiation

μ = 1.52 mm−1

T = 123 K

0.79 × 0.43 × 0.22 mm

Data collection

Agilent Xcalibur (Ruby, Gemini) diffractometer

Absorption correction: analytical (CrysAlis RED; Agilent, 2012 ▶) T min = 0.535, T max = 0.766

9563 measured reflections

9563 independent reflections

7477 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.163

S = 1.03

9563 reflections

373 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.77 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812048969/tk5176sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812048969/tk5176Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812048969/tk5176Isup3.cml

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

C27H29N5O6S·H2O	F(000) = 1200
Mr = 569.63	Dx = 1.385 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 3219 reflections
a = 12.3393 (4) Å	θ = 2.9–75.5°
b = 15.1238 (6) Å	µ = 1.52 mm−1
c = 14.6988 (4) Å	T = 123 K
β = 95.037 (3)°	Prism, colourless
V = 2732.46 (16) Å3	0.79 × 0.43 × 0.22 mm
Z = 4

Agilent Xcalibur (Ruby, Gemini) diffractometer	9563 independent reflections
Radiation source: Enhance (Cu) X-ray Source	7477 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
Detector resolution: 10.5081 pixels mm-1	θmax = 76.1°, θmin = 3.6°
ω scans	h = −15→14
Absorption correction: analytical (CrysAlis PRO; Agilent, 2012)	k = −18→18
Tmin = 0.535, Tmax = 0.766	l = −18→18
9563 measured reflections

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.1185P)2] where P = (Fo2 + 2Fc2)/3
9563 reflections	(Δ/σ)max < 0.001
373 parameters	Δρmax = 0.44 e Å−3
3 restraints	Δρmin = −0.77 e Å−3

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.

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 > 2sigma(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
S1	0.61088 (3)	0.25246 (3)	0.77145 (3)	0.02158 (12)
O1	0.52137 (11)	0.26956 (9)	0.70499 (10)	0.0278 (3)
O2	0.60422 (11)	0.17933 (9)	0.83307 (9)	0.0286 (3)
O3	0.90811 (10)	0.17574 (9)	0.64520 (9)	0.0223 (3)
O4	1.00833 (11)	0.03046 (9)	0.69883 (10)	0.0319 (3)
O5	0.96944 (10)	0.26749 (8)	0.49814 (9)	0.0211 (3)
O6	1.06737 (13)	0.43628 (11)	0.54935 (14)	0.0466 (5)
H6	1.0995	0.4851	0.5474	0.056*
O1W	0.80006 (14)	0.07096 (12)	0.78315 (12)	0.0431 (4)
H1W	0.8518 (18)	0.0432 (19)	0.772 (2)	0.065*
H2W	0.774 (2)	0.050 (2)	0.8265 (16)	0.065*
N1	0.72198 (13)	0.23031 (11)	0.72150 (11)	0.0240 (3)
H1A	0.7601	0.1839	0.7413	0.029*
N2	0.70609 (12)	0.35062 (10)	0.62171 (10)	0.0201 (3)
N3	0.83084 (11)	0.37054 (10)	0.50764 (10)	0.0193 (3)
N4	0.69029 (12)	0.49778 (11)	0.43244 (10)	0.0228 (3)
N5	0.63133 (12)	0.51751 (10)	0.58109 (11)	0.0216 (3)
C1	0.63930 (15)	0.34843 (13)	0.83661 (13)	0.0234 (4)
C2	0.61384 (14)	0.43168 (13)	0.80149 (12)	0.0229 (4)
H2A	0.5839	0.4383	0.7401	0.027*
C3	0.63269 (15)	0.50540 (13)	0.85735 (13)	0.0254 (4)
H3A	0.6144	0.5624	0.8337	0.031*
C4	0.67792 (16)	0.49731 (14)	0.94734 (13)	0.0274 (4)
C5	0.7032 (2)	0.41272 (16)	0.97988 (15)	0.0376 (5)
H5A	0.7348	0.4058	1.0407	0.045*
C6	0.68348 (19)	0.33858 (15)	0.92605 (15)	0.0354 (5)
H6A	0.7001	0.2814	0.9501	0.042*
C7	0.70065 (18)	0.57723 (14)	1.01064 (14)	0.0315 (4)
C8	0.6619 (3)	0.66378 (17)	0.96631 (19)	0.0588 (8)
H8A	0.5833	0.6609	0.9501	0.088*
H8B	0.6993	0.6736	0.9110	0.088*
H8C	0.6783	0.7126	1.0092	0.088*
C9	0.8239 (2)	0.5843 (2)	1.03558 (19)	0.0508 (7)
H9A	0.8390	0.6337	1.0779	0.076*
H9B	0.8607	0.5944	0.9801	0.076*
H9C	0.8507	0.5292	1.0647	0.076*
C10	0.6441 (2)	0.56343 (18)	1.09732 (16)	0.0451 (6)
H10A	0.5657	0.5565	1.0816	0.068*
H10B	0.6571	0.6148	1.1375	0.068*
H10C	0.6729	0.5102	1.1288	0.068*
C11	0.76040 (14)	0.27812 (12)	0.65145 (12)	0.0193 (4)
C12	0.85494 (14)	0.25075 (12)	0.61345 (12)	0.0194 (3)
C13	0.88431 (14)	0.29866 (12)	0.53861 (12)	0.0193 (3)
C14	0.74497 (13)	0.39270 (12)	0.55183 (12)	0.0189 (4)
C15	0.68504 (13)	0.47494 (12)	0.51997 (12)	0.0192 (3)
C16	0.63172 (15)	0.56851 (13)	0.40389 (13)	0.0251 (4)
H16A	0.6321	0.5865	0.3420	0.030*
C17	0.57088 (15)	0.61632 (12)	0.46094 (14)	0.0249 (4)
H17A	0.5281	0.6655	0.4395	0.030*
C18	0.57539 (14)	0.58898 (12)	0.55099 (14)	0.0244 (4)
H18A	0.5374	0.6222	0.5929	0.029*
C19	1.01482 (14)	0.18540 (13)	0.68486 (12)	0.0221 (4)
C20	1.06708 (15)	0.10674 (13)	0.71295 (13)	0.0252 (4)
C21	1.17366 (16)	0.11063 (15)	0.75333 (13)	0.0301 (4)
H21A	1.2102	0.0578	0.7729	0.036*
C22	1.22647 (16)	0.19136 (16)	0.76497 (13)	0.0328 (5)
H22A	1.2990	0.1936	0.7925	0.039*
C23	1.17412 (16)	0.26824 (15)	0.73685 (14)	0.0300 (4)
H23A	1.2105	0.3234	0.7451	0.036*
C24	1.06718 (15)	0.26529 (13)	0.69604 (12)	0.0245 (4)
H24A	1.0311	0.3183	0.6762	0.029*
C25	1.06856 (19)	−0.05017 (16)	0.7061 (2)	0.0476 (7)
H25A	1.0213	−0.0994	0.6847	0.071*
H25B	1.0954	−0.0601	0.7701	0.071*
H25C	1.1303	−0.0464	0.6687	0.071*
C26	1.02013 (15)	0.32487 (12)	0.43522 (12)	0.0233 (4)
H26A	0.9652	0.3658	0.4056	0.028*
H26B	1.0502	0.2890	0.3870	0.028*
C27	1.10957 (16)	0.37666 (15)	0.48616 (15)	0.0323 (5)
H27A	1.1613	0.3355	0.5195	0.039*
H27B	1.1498	0.4104	0.4422	0.039*

	U11	U22	U33	U12	U13	U23
S1	0.0224 (2)	0.0212 (2)	0.0225 (2)	−0.00108 (16)	0.00979 (17)	0.00304 (17)
O1	0.0249 (6)	0.0310 (7)	0.0278 (7)	−0.0014 (6)	0.0043 (5)	0.0023 (6)
O2	0.0328 (7)	0.0243 (7)	0.0309 (7)	−0.0008 (5)	0.0143 (6)	0.0062 (6)
O3	0.0210 (6)	0.0199 (6)	0.0267 (6)	0.0018 (5)	0.0055 (5)	0.0054 (5)
O4	0.0299 (7)	0.0247 (7)	0.0424 (8)	0.0056 (6)	0.0109 (6)	0.0106 (6)
O5	0.0216 (6)	0.0202 (6)	0.0228 (6)	0.0026 (5)	0.0095 (5)	0.0023 (5)
O6	0.0369 (8)	0.0366 (9)	0.0694 (12)	−0.0127 (7)	0.0228 (8)	−0.0265 (9)
O1W	0.0474 (9)	0.0412 (10)	0.0453 (10)	0.0189 (7)	0.0300 (8)	0.0228 (8)
N1	0.0266 (8)	0.0201 (8)	0.0271 (8)	0.0047 (6)	0.0125 (6)	0.0057 (6)
N2	0.0211 (7)	0.0189 (7)	0.0209 (7)	0.0013 (6)	0.0060 (6)	0.0008 (6)
N3	0.0213 (7)	0.0196 (7)	0.0174 (7)	0.0011 (6)	0.0050 (6)	0.0005 (6)
N4	0.0250 (7)	0.0230 (8)	0.0211 (7)	0.0019 (6)	0.0056 (6)	0.0018 (6)
N5	0.0216 (7)	0.0201 (7)	0.0238 (7)	0.0004 (6)	0.0055 (6)	−0.0004 (6)
C1	0.0250 (8)	0.0220 (9)	0.0244 (9)	0.0010 (7)	0.0082 (7)	0.0005 (7)
C2	0.0248 (8)	0.0247 (9)	0.0200 (8)	0.0008 (7)	0.0070 (7)	0.0040 (7)
C3	0.0276 (9)	0.0258 (9)	0.0238 (9)	0.0020 (7)	0.0075 (7)	0.0051 (8)
C4	0.0318 (10)	0.0272 (10)	0.0238 (9)	0.0008 (8)	0.0053 (8)	−0.0014 (8)
C5	0.0529 (13)	0.0321 (11)	0.0262 (10)	0.0074 (10)	−0.0055 (9)	0.0013 (9)
C6	0.0473 (12)	0.0284 (11)	0.0295 (11)	0.0073 (9)	−0.0014 (9)	0.0056 (9)
C7	0.0409 (11)	0.0285 (11)	0.0255 (10)	0.0000 (9)	0.0046 (8)	−0.0042 (9)
C8	0.105 (2)	0.0305 (13)	0.0398 (14)	0.0115 (14)	−0.0028 (15)	−0.0075 (11)
C9	0.0438 (13)	0.0553 (16)	0.0545 (16)	−0.0129 (12)	0.0121 (12)	−0.0205 (14)
C10	0.0534 (14)	0.0508 (15)	0.0335 (12)	−0.0131 (12)	0.0168 (11)	−0.0133 (11)
C11	0.0226 (8)	0.0179 (8)	0.0183 (8)	−0.0028 (6)	0.0061 (7)	−0.0018 (7)
C12	0.0210 (8)	0.0168 (8)	0.0207 (9)	0.0009 (6)	0.0040 (7)	0.0011 (7)
C13	0.0208 (8)	0.0193 (8)	0.0184 (8)	−0.0015 (6)	0.0053 (6)	−0.0020 (7)
C14	0.0206 (8)	0.0191 (9)	0.0173 (8)	−0.0012 (6)	0.0042 (6)	−0.0010 (7)
C15	0.0184 (7)	0.0183 (8)	0.0213 (8)	−0.0014 (6)	0.0045 (6)	−0.0004 (7)
C16	0.0273 (9)	0.0232 (9)	0.0247 (9)	0.0001 (7)	0.0026 (7)	0.0051 (8)
C17	0.0222 (8)	0.0183 (9)	0.0342 (10)	0.0006 (7)	0.0017 (7)	0.0025 (8)
C18	0.0226 (8)	0.0187 (8)	0.0326 (10)	0.0020 (7)	0.0062 (7)	−0.0028 (8)
C19	0.0212 (8)	0.0287 (10)	0.0175 (8)	0.0046 (7)	0.0071 (7)	0.0034 (7)
C20	0.0258 (9)	0.0285 (10)	0.0230 (9)	0.0068 (7)	0.0110 (7)	0.0074 (8)
C21	0.0293 (9)	0.0401 (12)	0.0220 (9)	0.0123 (8)	0.0078 (8)	0.0075 (8)
C22	0.0267 (10)	0.0491 (13)	0.0226 (9)	0.0051 (9)	0.0027 (8)	0.0023 (9)
C23	0.0277 (9)	0.0385 (12)	0.0239 (10)	−0.0031 (8)	0.0033 (7)	−0.0014 (9)
C24	0.0260 (9)	0.0296 (10)	0.0182 (9)	0.0025 (7)	0.0046 (7)	0.0007 (7)
C25	0.0388 (12)	0.0261 (11)	0.0796 (19)	0.0088 (9)	0.0140 (12)	0.0183 (12)
C26	0.0282 (9)	0.0229 (9)	0.0206 (9)	0.0027 (7)	0.0132 (7)	0.0016 (7)
C27	0.0274 (9)	0.0297 (11)	0.0422 (12)	−0.0023 (8)	0.0163 (9)	−0.0050 (9)

S1—O1	1.4324 (14)	C7—C9	1.537 (3)
S1—O2	1.4365 (14)	C8—H8A	0.9800
S1—N1	1.6455 (15)	C8—H8B	0.9800
S1—C1	1.757 (2)	C8—H8C	0.9800
O3—C12	1.372 (2)	C9—H9A	0.9800
O3—C19	1.400 (2)	C9—H9B	0.9800
O4—C20	1.369 (2)	C9—H9C	0.9800
O4—C25	1.427 (2)	C10—H10A	0.9800
O5—C13	1.338 (2)	C10—H10B	0.9800
O5—C26	1.450 (2)	C10—H10C	0.9800
O6—C27	1.425 (2)	C11—C12	1.400 (2)
O6—H6	0.8400	C12—C13	1.392 (2)
O1W—H1W	0.795 (16)	C14—C15	1.501 (2)
O1W—H2W	0.805 (16)	C16—C17	1.378 (3)
N1—C11	1.376 (2)	C16—H16A	0.9500
N1—H1A	0.8800	C17—C18	1.383 (3)
N2—C14	1.333 (2)	C17—H17A	0.9500
N2—C11	1.338 (2)	C18—H18A	0.9500
N3—C13	1.331 (2)	C19—C24	1.373 (3)
N3—C14	1.333 (2)	C19—C20	1.398 (3)
N4—C16	1.338 (2)	C20—C21	1.396 (3)
N4—C15	1.339 (2)	C21—C22	1.387 (3)
N5—C15	1.329 (2)	C21—H21A	0.9500
N5—C18	1.337 (2)	C22—C23	1.376 (3)
C1—C6	1.386 (3)	C22—H22A	0.9500
C1—C2	1.386 (3)	C23—C24	1.401 (3)
C2—C3	1.392 (3)	C23—H23A	0.9500
C2—H2A	0.9500	C24—H24A	0.9500
C3—C4	1.395 (3)	C25—H25A	0.9800
C3—H3A	0.9500	C25—H25B	0.9800
C4—C5	1.391 (3)	C25—H25C	0.9800
C4—C7	1.536 (3)	C26—C27	1.499 (3)
C5—C6	1.381 (3)	C26—H26A	0.9900
C5—H5A	0.9500	C26—H26B	0.9900
C6—H6A	0.9500	C27—H27A	0.9900
C7—C10	1.520 (3)	C27—H27B	0.9900
C7—C8	1.520 (3)
O1—S1—O2	119.06 (9)	N2—C11—N1	118.65 (15)
O1—S1—N1	110.81 (8)	N2—C11—C12	121.54 (16)
O2—S1—N1	102.75 (8)	N1—C11—C12	119.81 (17)
O1—S1—C1	109.13 (9)	O3—C12—C13	123.34 (16)
O2—S1—C1	108.18 (9)	O3—C12—C11	119.96 (16)
N1—S1—C1	106.09 (9)	C13—C12—C11	116.46 (16)
C12—O3—C19	117.36 (14)	N3—C13—O5	121.38 (15)
C20—O4—C25	116.32 (16)	N3—C13—C12	122.68 (16)
C13—O5—C26	118.20 (14)	O5—C13—C12	115.93 (16)
C27—O6—H6	109.5	N2—C14—N3	127.63 (17)
H1W—O1W—H2W	110 (2)	N2—C14—C15	115.81 (15)
C11—N1—S1	125.60 (13)	N3—C14—C15	116.56 (15)
C11—N1—H1A	117.2	N5—C15—N4	126.42 (17)
S1—N1—H1A	117.2	N5—C15—C14	116.86 (16)
C14—N2—C11	116.05 (15)	N4—C15—C14	116.71 (15)
C13—N3—C14	115.46 (15)	N4—C16—C17	122.46 (18)
C16—N4—C15	115.93 (16)	N4—C16—H16A	118.8
C15—N5—C18	116.21 (16)	C17—C16—H16A	118.8
C6—C1—C2	120.54 (18)	C16—C17—C18	116.55 (17)
C6—C1—S1	118.11 (15)	C16—C17—H17A	121.7
C2—C1—S1	121.29 (15)	C18—C17—H17A	121.7
C1—C2—C3	119.15 (17)	N5—C18—C17	122.32 (17)
C1—C2—H2A	120.4	N5—C18—H18A	118.8
C3—C2—H2A	120.4	C17—C18—H18A	118.8
C2—C3—C4	121.41 (18)	C24—C19—C20	120.89 (18)
C2—C3—H3A	119.3	C24—C19—O3	123.86 (17)
C4—C3—H3A	119.3	C20—C19—O3	115.26 (17)
C5—C4—C3	117.74 (19)	O4—C20—C21	124.53 (18)
C5—C4—C7	119.46 (18)	O4—C20—C19	116.62 (17)
C3—C4—C7	122.81 (19)	C21—C20—C19	118.85 (19)
C6—C5—C4	121.77 (19)	C22—C21—C20	120.29 (19)
C6—C5—H5A	119.1	C22—C21—H21A	119.9
C4—C5—H5A	119.1	C20—C21—H21A	119.9
C5—C6—C1	119.39 (19)	C23—C22—C21	120.24 (19)
C5—C6—H6A	120.3	C23—C22—H22A	119.9
C1—C6—H6A	120.3	C21—C22—H22A	119.9
C10—C7—C8	109.1 (2)	C22—C23—C24	120.1 (2)
C10—C7—C4	109.08 (18)	C22—C23—H23A	120.0
C8—C7—C4	112.58 (18)	C24—C23—H23A	120.0
C10—C7—C9	109.1 (2)	C19—C24—C23	119.65 (19)
C8—C7—C9	108.1 (2)	C19—C24—H24A	120.2
C4—C7—C9	108.85 (18)	C23—C24—H24A	120.2
C7—C8—H8A	109.5	O4—C25—H25A	109.5
C7—C8—H8B	109.5	O4—C25—H25B	109.5
H8A—C8—H8B	109.5	H25A—C25—H25B	109.5
C7—C8—H8C	109.5	O4—C25—H25C	109.5
H8A—C8—H8C	109.5	H25A—C25—H25C	109.5
H8B—C8—H8C	109.5	H25B—C25—H25C	109.5
C7—C9—H9A	109.5	O5—C26—C27	109.51 (15)
C7—C9—H9B	109.5	O5—C26—H26A	109.8
H9A—C9—H9B	109.5	C27—C26—H26A	109.8
C7—C9—H9C	109.5	O5—C26—H26B	109.8
H9A—C9—H9C	109.5	C27—C26—H26B	109.8
H9B—C9—H9C	109.5	H26A—C26—H26B	108.2
C7—C10—H10A	109.5	O6—C27—C26	111.16 (16)
C7—C10—H10B	109.5	O6—C27—H27A	109.4
H10A—C10—H10B	109.5	C26—C27—H27A	109.4
C7—C10—H10C	109.5	O6—C27—H27B	109.4
H10A—C10—H10C	109.5	C26—C27—H27B	109.4
H10B—C10—H10C	109.5	H27A—C27—H27B	108.0
O1—S1—N1—C11	47.22 (18)	C26—O5—C13—C12	−165.22 (15)
O2—S1—N1—C11	175.43 (16)	O3—C12—C13—N3	178.87 (16)
C1—S1—N1—C11	−71.10 (18)	C11—C12—C13—N3	4.5 (3)
O1—S1—C1—C6	150.77 (16)	O3—C12—C13—O5	−0.3 (3)
O2—S1—C1—C6	19.86 (18)	C11—C12—C13—O5	−174.61 (16)
N1—S1—C1—C6	−89.80 (17)	C11—N2—C14—N3	0.7 (3)
O1—S1—C1—C2	−26.27 (17)	C11—N2—C14—C15	−178.84 (15)
O2—S1—C1—C2	−157.18 (15)	C13—N3—C14—N2	−1.2 (3)
N1—S1—C1—C2	93.16 (16)	C13—N3—C14—C15	178.36 (15)
C6—C1—C2—C3	−0.3 (3)	C18—N5—C15—N4	1.6 (3)
S1—C1—C2—C3	176.65 (13)	C18—N5—C15—C14	−177.86 (15)
C1—C2—C3—C4	0.9 (3)	C16—N4—C15—N5	−2.9 (3)
C2—C3—C4—C5	−0.4 (3)	C16—N4—C15—C14	176.55 (15)
C2—C3—C4—C7	179.51 (17)	N2—C14—C15—N5	26.1 (2)
C3—C4—C5—C6	−0.7 (3)	N3—C14—C15—N5	−153.49 (16)
C7—C4—C5—C6	179.4 (2)	N2—C14—C15—N4	−153.35 (16)
C4—C5—C6—C1	1.2 (4)	N3—C14—C15—N4	27.0 (2)
C2—C1—C6—C5	−0.7 (3)	C15—N4—C16—C17	1.1 (3)
S1—C1—C6—C5	−177.78 (18)	N4—C16—C17—C18	1.7 (3)
C5—C4—C7—C10	−55.2 (3)	C15—N5—C18—C17	1.6 (3)
C3—C4—C7—C10	124.9 (2)	C16—C17—C18—N5	−3.1 (3)
C5—C4—C7—C8	−176.5 (2)	C12—O3—C19—C24	2.1 (2)
C3—C4—C7—C8	3.7 (3)	C12—O3—C19—C20	−177.61 (15)
C5—C4—C7—C9	63.8 (3)	C25—O4—C20—C21	−15.3 (3)
C3—C4—C7—C9	−116.1 (2)	C25—O4—C20—C19	165.06 (19)
C14—N2—C11—N1	−177.91 (16)	C24—C19—C20—O4	−179.91 (16)
C14—N2—C11—C12	2.5 (3)	O3—C19—C20—O4	−0.2 (2)
S1—N1—C11—N2	2.0 (3)	C24—C19—C20—C21	0.4 (3)
S1—N1—C11—C12	−178.44 (14)	O3—C19—C20—C21	−179.89 (15)
C19—O3—C12—C13	68.0 (2)	O4—C20—C21—C22	−179.81 (18)
C19—O3—C12—C11	−117.88 (18)	C19—C20—C21—C22	−0.2 (3)
N2—C11—C12—O3	−179.54 (16)	C20—C21—C22—C23	0.1 (3)
N1—C11—C12—O3	0.9 (3)	C21—C22—C23—C24	−0.2 (3)
N2—C11—C12—C13	−5.0 (3)	C20—C19—C24—C23	−0.5 (3)
N1—C11—C12—C13	175.48 (16)	O3—C19—C24—C23	179.80 (16)
C14—N3—C13—O5	177.48 (16)	C22—C23—C24—C19	0.4 (3)
C14—N3—C13—C12	−1.6 (3)	C13—O5—C26—C27	90.58 (19)
C26—O5—C13—N3	15.6 (2)	O5—C26—C27—O6	−65.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···N3i	0.84	2.51	3.317 (2)	162
O6—H6···N4i	0.84	2.60	3.141 (2)	124
O1W—H1W···O4	0.80 (2)	2.30 (2)	3.013 (2)	150 (3)
O1W—H2W···N4ii	0.81 (2)	2.07 (2)	2.873 (2)	174 (3)
N1—H1A···O1W	0.88	1.87	2.721 (2)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6⋯N3i	0.84	2.51	3.317 (2)	162
O6—H6⋯N4i	0.84	2.60	3.141 (2)	124
O1W—H1W⋯O4	0.80 (2)	2.30 (2)	3.013 (2)	150 (3)
O1W—H2W⋯N4ii	0.81 (2)	2.07 (2)	2.873 (2)	174 (3)
N1—H1A⋯O1W	0.88	1.87	2.721 (2)	163

Symmetry codes: (i) ; (ii) .