2-{[5-(Pyridin-4-yl)-4-p-tolyl-4H-1,2,4-triazol-3-yl]meth-yl}acrylic acid hemi-hydrate.

The asymmetric unit of the title compound, 2C18H16N4O2·H2O, consists of two organic molecules and one solvent molecule. The symmetry-independent organic mol-ecules have slightly different conformations: the 1,2,4-triazole ring forms dihedral angles of 84.61 (4), 89.68 (5) and 22.38 (6)°, respectively, with the 2-propenecarbocylic, p-tolyl and 4-pyridyl groups in one independent molecule, and 71.35 (4), 82.13 (5) and 24.82 (6)°, respectively, in the second. In the crystal, mol-ecules ralated by the 21 screw axes are assembled via O-H⋯N and O-H⋯O hydrogen bonds into infinite chains and these are linked by further O-H⋯N hydrogen bonds into undulating sheets parallel to the bc plane. Adjacent sheets are connected by weak C-H⋯O inter-actions, forming a three-dimensional structure.

Related literature

For the pharmacological activity of 1,2,4-triazole derivatives, see: Amir & Shikha (2004 ▶); El-Serwy et al. (2013 ▶); McDowell et al. (2010 ▶); Modzelewska-Banachiewicz, Paprocka et al. (2012 ▶); Modzelewska-Banachiewicz, Ucherek et al. (2012 ▶); Siddiqui & Ahsan (2010 ▶); Sztanke et al. (2008 ▶); Wang et al. (2000 ▶).

Experimental

Crystal data

2C18H16N4O2·H2O

M = 658.71

Monoclinic,

a = 10.0344 (1) Å

b = 16.1485 (2) Å

c = 20.1650 (3) Å

β = 98.699 (1)°

V = 3229.96 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 130 K

0.55 × 0.30 × 0.10 mm

Data collection

Agilent Xcalibur Atlas diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.991, T max = 1.000

22090 measured reflections

7724 independent reflections

6542 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.119

S = 1.03

7724 reflections

460 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.80 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, publication_text. DOI: 10.1107/S1600536813034077/bt6951sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813034077/bt6951Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813034077/bt6951Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

2C18H16N4O2·H2O	F(000) = 1384
Mr = 658.71	Dx = 1.355 Mg m−3
Monoclinic, P21/n	Melting point = 416–418 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 10.0344 (1) Å	Cell parameters from 9224 reflections
b = 16.1485 (2) Å	θ = 2.0–29.1°
c = 20.1650 (3) Å	µ = 0.09 mm−1
β = 98.699 (1)°	T = 130 K
V = 3229.96 (7) Å3	Lath, colourless
Z = 4	0.55 × 0.30 × 0.10 mm

Agilent Xcalibur Atlas diffractometer	7724 independent reflections
Radiation source: Enhance (Mo) X-ray Source	6542 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
Detector resolution: 10.3088 pixels mm-1	θmax = 29.2°, θmin = 2.2°
ω scans	h = −13→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −18→21
Tmin = 0.991, Tmax = 1.000	l = −26→27
22090 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0533P)2 + 1.7812P] where P = (Fo2 + 2Fc2)/3
7724 reflections	(Δ/σ)max < 0.001
460 parameters	Δρmax = 0.80 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

Experimental. none

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
N1A	0.13167 (12)	0.47922 (8)	0.35710 (6)	0.0239 (3)
N2A	0.03447 (12)	0.43871 (8)	0.38651 (6)	0.0246 (3)
C3A	−0.06428 (14)	0.42016 (8)	0.33856 (7)	0.0210 (3)
N4A	−0.03617 (11)	0.44814 (7)	0.27792 (6)	0.0194 (2)
C5A	0.08908 (13)	0.48407 (8)	0.29241 (7)	0.0201 (3)
C6A	−0.18670 (14)	0.37179 (9)	0.34822 (7)	0.0234 (3)
H6A1	−0.2355	0.3558	0.3049	0.028*
H6A2	−0.2457	0.4060	0.3706	0.028*
C7A	−0.14745 (13)	0.29541 (9)	0.38961 (7)	0.0213 (3)
C8A	−0.17641 (16)	0.28325 (11)	0.45081 (8)	0.0326 (3)
H8A1	−0.1459	0.2358	0.4745	0.039*
H8A2	−0.2272	0.3221	0.4701	0.039*
C9A	−0.06644 (13)	0.23433 (9)	0.35751 (7)	0.0202 (3)
O10A	−0.03092 (11)	0.24626 (7)	0.30337 (5)	0.0292 (2)
O11A	−0.03137 (11)	0.16726 (7)	0.39398 (5)	0.0257 (2)
H11A	0.033 (3)	0.1388 (16)	0.3757 (12)	0.067 (7)*
C12A	−0.11815 (13)	0.43501 (8)	0.21379 (7)	0.0197 (3)
C13A	−0.21393 (14)	0.49326 (9)	0.18935 (8)	0.0274 (3)
H13A	−0.2255	0.5407	0.2140	0.033*
C14A	−0.29256 (15)	0.48007 (10)	0.12756 (8)	0.0299 (3)
H14A	−0.3558	0.5197	0.1104	0.036*
C15A	−0.27859 (14)	0.40888 (10)	0.09086 (7)	0.0253 (3)
C16A	−0.18208 (17)	0.35127 (10)	0.11710 (7)	0.0298 (3)
H16A	−0.1715	0.3032	0.0931	0.036*
C17A	−0.10138 (16)	0.36387 (9)	0.17820 (7)	0.0271 (3)
H17A	−0.0368	0.3249	0.1950	0.033*
C18A	−0.36508 (17)	0.39371 (12)	0.02439 (8)	0.0362 (4)
H18A	−0.4299	0.4375	0.0153	0.054*
H18B	−0.4113	0.3418	0.0257	0.054*
H18C	−0.3094	0.3921	−0.0103	0.054*
C19A	0.17137 (13)	0.51971 (8)	0.24532 (7)	0.0200 (3)
C20A	0.12086 (14)	0.54991 (9)	0.18206 (7)	0.0252 (3)
H20A	0.0289	0.5482	0.1664	0.030*
C21A	0.20962 (15)	0.58253 (9)	0.14279 (8)	0.0271 (3)
H21A	0.1746	0.6030	0.1006	0.033*
N22A	0.34290 (12)	0.58630 (8)	0.16195 (6)	0.0254 (3)
C23A	0.39050 (14)	0.55747 (9)	0.22296 (8)	0.0268 (3)
H23A	0.4830	0.5600	0.2372	0.032*
C24A	0.31073 (14)	0.52426 (9)	0.26586 (7)	0.0244 (3)
H24A	0.3488	0.5051	0.3080	0.029*
N1B	0.37740 (12)	0.80883 (8)	0.70883 (6)	0.0239 (3)
N2B	0.45728 (12)	0.77341 (8)	0.66600 (6)	0.0246 (3)
C3B	0.56239 (14)	0.74131 (9)	0.70340 (7)	0.0213 (3)
N4B	0.55646 (11)	0.75461 (7)	0.77019 (6)	0.0203 (2)
C5B	0.43786 (13)	0.79731 (8)	0.77051 (7)	0.0204 (3)
C6B	0.67580 (14)	0.69625 (10)	0.67849 (7)	0.0259 (3)
H6B1	0.6900	0.6435	0.7015	0.031*
H6B2	0.7579	0.7284	0.6890	0.031*
C7B	0.64739 (14)	0.68143 (9)	0.60410 (7)	0.0246 (3)
C8B	0.72326 (16)	0.71225 (11)	0.56226 (9)	0.0337 (4)
H8B1	0.7074	0.6975	0.5172	0.040*
H8B2	0.7927	0.7487	0.5778	0.040*
C9B	0.53499 (14)	0.62252 (9)	0.57998 (7)	0.0221 (3)
O10B	0.48977 (10)	0.57518 (7)	0.61765 (5)	0.0273 (2)
O11B	0.49295 (11)	0.62687 (7)	0.51487 (5)	0.0279 (2)
H11B	0.419 (2)	0.5879 (14)	0.5013 (11)	0.053 (6)*
C12B	0.64672 (14)	0.72110 (9)	0.82592 (7)	0.0206 (3)
C13B	0.61305 (16)	0.64845 (9)	0.85523 (8)	0.0270 (3)
H13B	0.5334	0.6210	0.8388	0.032*
C14B	0.69968 (17)	0.61681 (10)	0.90969 (8)	0.0320 (3)
H14B	0.6775	0.5676	0.9294	0.038*
C15B	0.81822 (16)	0.65707 (11)	0.93523 (8)	0.0316 (3)
C16B	0.84978 (16)	0.73014 (11)	0.90471 (8)	0.0325 (3)
H16B	0.9288	0.7581	0.9214	0.039*
C17B	0.76551 (15)	0.76198 (10)	0.84992 (8)	0.0280 (3)
H17B	0.7885	0.8104	0.8294	0.034*
C18B	0.9097 (2)	0.62366 (14)	0.99552 (9)	0.0495 (5)
H18D	0.8716	0.5739	1.0107	0.074*
H18E	0.9192	0.6642	1.0308	0.074*
H18F	0.9966	0.6116	0.9834	0.074*
C19B	0.38527 (14)	0.83183 (8)	0.82898 (7)	0.0207 (3)
C20B	0.46609 (15)	0.85228 (9)	0.88900 (7)	0.0258 (3)
H20B	0.5573	0.8390	0.8961	0.031*
C21B	0.40785 (16)	0.89298 (10)	0.93822 (8)	0.0285 (3)
H21B	0.4625	0.9062	0.9783	0.034*
N22B	0.27817 (13)	0.91411 (8)	0.93119 (6)	0.0284 (3)
C23B	0.20068 (15)	0.89272 (10)	0.87382 (8)	0.0281 (3)
H23B	0.1097	0.9064	0.8684	0.034*
C24B	0.24830 (15)	0.85145 (9)	0.82223 (7)	0.0249 (3)
H24B	0.1901	0.8369	0.7836	0.030*
O25	0.28894 (12)	0.53329 (7)	0.47820 (6)	0.0319 (3)
H25A	0.254 (2)	0.5184 (13)	0.4385 (12)	0.045 (6)*
H25B	0.274 (2)	0.4899 (16)	0.5073 (12)	0.064 (7)*

	U11	U22	U33	U12	U13	U23
N1A	0.0241 (6)	0.0267 (6)	0.0205 (6)	−0.0052 (5)	0.0021 (5)	−0.0002 (5)
N2A	0.0250 (6)	0.0275 (6)	0.0214 (6)	−0.0050 (5)	0.0034 (5)	0.0003 (5)
C3A	0.0222 (6)	0.0203 (6)	0.0206 (7)	0.0014 (5)	0.0038 (5)	0.0000 (5)
N4A	0.0187 (5)	0.0199 (5)	0.0192 (6)	−0.0007 (4)	0.0019 (4)	−0.0013 (4)
C5A	0.0202 (6)	0.0188 (6)	0.0208 (6)	−0.0008 (5)	0.0013 (5)	−0.0011 (5)
C6A	0.0194 (6)	0.0257 (7)	0.0253 (7)	0.0004 (5)	0.0044 (5)	0.0006 (6)
C7A	0.0171 (6)	0.0241 (7)	0.0228 (7)	−0.0034 (5)	0.0034 (5)	−0.0009 (5)
C8A	0.0334 (8)	0.0355 (9)	0.0308 (8)	0.0030 (7)	0.0110 (7)	0.0028 (7)
C9A	0.0175 (6)	0.0241 (7)	0.0180 (6)	−0.0030 (5)	−0.0010 (5)	−0.0010 (5)
O10A	0.0352 (6)	0.0332 (6)	0.0205 (5)	0.0071 (5)	0.0084 (4)	0.0026 (4)
O11A	0.0264 (5)	0.0267 (5)	0.0244 (5)	0.0035 (4)	0.0057 (4)	0.0039 (4)
C12A	0.0184 (6)	0.0211 (6)	0.0189 (6)	−0.0020 (5)	0.0011 (5)	0.0000 (5)
C13A	0.0241 (7)	0.0243 (7)	0.0321 (8)	0.0030 (6)	−0.0016 (6)	−0.0065 (6)
C14A	0.0235 (7)	0.0306 (8)	0.0330 (8)	0.0066 (6)	−0.0039 (6)	−0.0006 (7)
C15A	0.0235 (7)	0.0320 (8)	0.0199 (7)	−0.0034 (6)	0.0017 (5)	0.0013 (6)
C16A	0.0432 (9)	0.0254 (7)	0.0199 (7)	0.0043 (6)	0.0016 (6)	−0.0033 (6)
C17A	0.0345 (8)	0.0254 (7)	0.0207 (7)	0.0087 (6)	0.0016 (6)	0.0007 (6)
C18A	0.0346 (8)	0.0482 (10)	0.0234 (8)	0.0012 (7)	−0.0030 (6)	−0.0034 (7)
C19A	0.0213 (6)	0.0170 (6)	0.0215 (7)	−0.0012 (5)	0.0025 (5)	−0.0011 (5)
C20A	0.0201 (6)	0.0269 (7)	0.0277 (7)	0.0007 (5)	0.0011 (5)	0.0046 (6)
C21A	0.0268 (7)	0.0279 (7)	0.0258 (7)	−0.0003 (6)	0.0018 (6)	0.0062 (6)
N22A	0.0251 (6)	0.0246 (6)	0.0266 (6)	−0.0043 (5)	0.0045 (5)	0.0012 (5)
C23A	0.0203 (6)	0.0298 (8)	0.0293 (8)	−0.0039 (6)	0.0007 (6)	−0.0006 (6)
C24A	0.0245 (7)	0.0258 (7)	0.0215 (7)	−0.0033 (6)	−0.0012 (5)	0.0014 (6)
N1B	0.0249 (6)	0.0262 (6)	0.0203 (6)	0.0031 (5)	0.0028 (5)	−0.0024 (5)
N2B	0.0255 (6)	0.0275 (6)	0.0208 (6)	0.0030 (5)	0.0039 (5)	−0.0034 (5)
C3B	0.0232 (6)	0.0212 (7)	0.0191 (6)	−0.0021 (5)	0.0015 (5)	−0.0034 (5)
N4B	0.0207 (5)	0.0219 (6)	0.0178 (5)	0.0012 (4)	0.0013 (4)	−0.0014 (4)
C5B	0.0208 (6)	0.0198 (6)	0.0203 (6)	0.0006 (5)	0.0019 (5)	−0.0003 (5)
C6B	0.0222 (7)	0.0302 (7)	0.0249 (7)	−0.0009 (6)	0.0025 (5)	−0.0067 (6)
C7B	0.0217 (6)	0.0267 (7)	0.0254 (7)	0.0008 (5)	0.0036 (5)	−0.0060 (6)
C8B	0.0313 (8)	0.0373 (9)	0.0331 (8)	−0.0058 (7)	0.0072 (7)	−0.0080 (7)
C9B	0.0204 (6)	0.0244 (7)	0.0212 (7)	0.0028 (5)	0.0024 (5)	−0.0023 (5)
O10B	0.0262 (5)	0.0300 (6)	0.0249 (5)	−0.0029 (4)	0.0018 (4)	0.0022 (4)
O11B	0.0282 (5)	0.0326 (6)	0.0218 (5)	−0.0067 (5)	0.0001 (4)	−0.0004 (4)
C12B	0.0231 (6)	0.0214 (7)	0.0168 (6)	0.0038 (5)	0.0011 (5)	−0.0020 (5)
C13B	0.0294 (7)	0.0241 (7)	0.0273 (7)	−0.0013 (6)	0.0035 (6)	−0.0011 (6)
C14B	0.0410 (9)	0.0277 (8)	0.0279 (8)	0.0073 (7)	0.0072 (7)	0.0066 (6)
C15B	0.0352 (8)	0.0384 (9)	0.0205 (7)	0.0154 (7)	0.0020 (6)	−0.0020 (6)
C16B	0.0260 (7)	0.0380 (9)	0.0306 (8)	0.0034 (6)	−0.0051 (6)	−0.0062 (7)
C17B	0.0269 (7)	0.0268 (7)	0.0287 (8)	−0.0015 (6)	−0.0006 (6)	0.0001 (6)
C18B	0.0492 (11)	0.0654 (13)	0.0305 (9)	0.0223 (10)	−0.0048 (8)	0.0064 (9)
C19B	0.0252 (7)	0.0183 (6)	0.0189 (6)	0.0016 (5)	0.0043 (5)	0.0017 (5)
C20B	0.0255 (7)	0.0282 (7)	0.0231 (7)	0.0045 (6)	0.0018 (6)	−0.0021 (6)
C21B	0.0333 (8)	0.0309 (8)	0.0209 (7)	0.0031 (6)	0.0026 (6)	−0.0023 (6)
N22B	0.0345 (7)	0.0300 (7)	0.0219 (6)	0.0056 (5)	0.0078 (5)	0.0005 (5)
C23B	0.0266 (7)	0.0328 (8)	0.0257 (7)	0.0054 (6)	0.0068 (6)	0.0020 (6)
C24B	0.0260 (7)	0.0275 (7)	0.0210 (7)	0.0024 (6)	0.0027 (5)	0.0007 (6)
O25	0.0368 (6)	0.0364 (6)	0.0203 (5)	−0.0149 (5)	−0.0025 (5)	0.0010 (5)

N1A—C5A	1.3121 (18)	N1B—N2B	1.3875 (16)
N1A—N2A	1.3806 (16)	N2B—C3B	1.3073 (19)
N2A—C3A	1.3102 (18)	C3B—N4B	1.3740 (17)
C3A—N4A	1.3722 (17)	C3B—C6B	1.4999 (19)
C3A—C6A	1.4932 (19)	N4B—C5B	1.3763 (17)
N4A—C5A	1.3750 (17)	N4B—C12B	1.4381 (17)
N4A—C12A	1.4396 (17)	C5B—C19B	1.4722 (19)
C5A—C19A	1.4670 (18)	C6B—C7B	1.503 (2)
C6A—C7A	1.508 (2)	C6B—H6B1	0.9700
C6A—H6A1	0.9700	C6B—H6B2	0.9700
C6A—H6A2	0.9700	C7B—C8B	1.317 (2)
C7A—C8A	1.325 (2)	C7B—C9B	1.499 (2)
C7A—C9A	1.4871 (19)	C8B—H8B1	0.9300
C8A—H8A1	0.9300	C8B—H8B2	0.9300
C8A—H8A2	0.9300	C9B—O10B	1.2132 (17)
C9A—O10A	1.2140 (17)	C9B—O11B	1.3187 (17)
C9A—O11A	1.3263 (17)	O11B—H11B	0.98 (2)
O11A—H11A	0.91 (3)	C12B—C13B	1.379 (2)
C12A—C17A	1.378 (2)	C12B—C17B	1.384 (2)
C12A—C13A	1.381 (2)	C13B—C14B	1.391 (2)
C13A—C14A	1.387 (2)	C13B—H13B	0.9300
C13A—H13A	0.9300	C14B—C15B	1.385 (2)
C14A—C15A	1.386 (2)	C14B—H14B	0.9300
C14A—H14A	0.9300	C15B—C16B	1.389 (2)
C15A—C16A	1.389 (2)	C15B—C18B	1.508 (2)
C15A—C18A	1.503 (2)	C16B—C17B	1.385 (2)
C16A—C17A	1.383 (2)	C16B—H16B	0.9300
C16A—H16A	0.9300	C17B—H17B	0.9300
C17A—H17A	0.9300	C18B—H18D	0.9600
C18A—H18A	0.9600	C18B—H18E	0.9600
C18A—H18B	0.9600	C18B—H18F	0.9600
C18A—H18C	0.9600	C19B—C20B	1.391 (2)
C19A—C20A	1.388 (2)	C19B—C24B	1.397 (2)
C19A—C24A	1.3991 (19)	C20B—C21B	1.391 (2)
C20A—C21A	1.382 (2)	C20B—H20B	0.9300
C20A—H20A	0.9300	C21B—N22B	1.332 (2)
C21A—N22A	1.3362 (19)	C21B—H21B	0.9300
C21A—H21A	0.9300	N22B—C23B	1.338 (2)
N22A—C23A	1.3344 (19)	C23B—C24B	1.380 (2)
C23A—C24A	1.373 (2)	C23B—H23B	0.9300
C23A—H23A	0.9300	C24B—H24B	0.9300
C24A—H24A	0.9300	O25—H25A	0.86 (2)
N1B—C5B	1.3120 (18)	O25—H25B	0.94 (3)
C5A—N1A—N2A	108.07 (11)	C3B—N2B—N1B	107.22 (11)
C3A—N2A—N1A	107.22 (11)	N2B—C3B—N4B	110.65 (12)
N2A—C3A—N4A	110.36 (12)	N2B—C3B—C6B	125.87 (13)
N2A—C3A—C6A	124.65 (13)	N4B—C3B—C6B	123.48 (12)
N4A—C3A—C6A	124.93 (12)	C3B—N4B—C5B	104.39 (11)
C3A—N4A—C5A	104.72 (11)	C3B—N4B—C12B	126.28 (11)
C3A—N4A—C12A	125.84 (11)	C5B—N4B—C12B	128.88 (11)
C5A—N4A—C12A	129.25 (11)	N1B—C5B—N4B	110.05 (12)
N1A—C5A—N4A	109.63 (12)	N1B—C5B—C19B	122.35 (12)
N1A—C5A—C19A	122.44 (12)	N4B—C5B—C19B	127.47 (12)
N4A—C5A—C19A	127.87 (12)	C3B—C6B—C7B	111.87 (12)
C3A—C6A—C7A	110.42 (11)	C3B—C6B—H6B1	109.2
C3A—C6A—H6A1	109.6	C7B—C6B—H6B1	109.2
C7A—C6A—H6A1	109.6	C3B—C6B—H6B2	109.2
C3A—C6A—H6A2	109.6	C7B—C6B—H6B2	109.2
C7A—C6A—H6A2	109.6	H6B1—C6B—H6B2	107.9
H6A1—C6A—H6A2	108.1	C8B—C7B—C9B	120.77 (14)
C8A—C7A—C9A	121.23 (14)	C8B—C7B—C6B	122.58 (14)
C8A—C7A—C6A	124.14 (14)	C9B—C7B—C6B	116.40 (13)
C9A—C7A—C6A	114.58 (12)	C7B—C8B—H8B1	120.0
C7A—C8A—H8A1	120.0	C7B—C8B—H8B2	120.0
C7A—C8A—H8A2	120.0	H8B1—C8B—H8B2	120.0
H8A1—C8A—H8A2	120.0	O10B—C9B—O11B	124.29 (13)
O10A—C9A—O11A	122.60 (13)	O10B—C9B—C7B	122.07 (13)
O10A—C9A—C7A	122.70 (13)	O11B—C9B—C7B	113.63 (12)
O11A—C9A—C7A	114.65 (12)	C9B—O11B—H11B	111.0 (13)
C9A—O11A—H11A	109.4 (16)	C13B—C12B—C17B	120.66 (13)
C17A—C12A—C13A	121.00 (13)	C13B—C12B—N4B	119.28 (13)
C17A—C12A—N4A	119.49 (12)	C17B—C12B—N4B	120.06 (13)
C13A—C12A—N4A	119.50 (12)	C12B—C13B—C14B	119.13 (14)
C12A—C13A—C14A	119.11 (14)	C12B—C13B—H13B	120.4
C12A—C13A—H13A	120.4	C14B—C13B—H13B	120.4
C14A—C13A—H13A	120.4	C15B—C14B—C13B	121.37 (15)
C15A—C14A—C13A	121.16 (14)	C15B—C14B—H14B	119.3
C15A—C14A—H14A	119.4	C13B—C14B—H14B	119.3
C13A—C14A—H14A	119.4	C14B—C15B—C16B	118.32 (14)
C14A—C15A—C16A	118.25 (14)	C14B—C15B—C18B	121.06 (17)
C14A—C15A—C18A	121.34 (14)	C16B—C15B—C18B	120.60 (17)
C16A—C15A—C18A	120.40 (14)	C17B—C16B—C15B	121.08 (15)
C17A—C16A—C15A	121.42 (14)	C17B—C16B—H16B	119.5
C17A—C16A—H16A	119.3	C15B—C16B—H16B	119.5
C15A—C16A—H16A	119.3	C12B—C17B—C16B	119.43 (15)
C12A—C17A—C16A	119.03 (14)	C12B—C17B—H17B	120.3
C12A—C17A—H17A	120.5	C16B—C17B—H17B	120.3
C16A—C17A—H17A	120.5	C15B—C18B—H18D	109.5
C15A—C18A—H18A	109.5	C15B—C18B—H18E	109.5
C15A—C18A—H18B	109.5	H18D—C18B—H18E	109.5
H18A—C18A—H18B	109.5	C15B—C18B—H18F	109.5
C15A—C18A—H18C	109.5	H18D—C18B—H18F	109.5
H18A—C18A—H18C	109.5	H18E—C18B—H18F	109.5
H18B—C18A—H18C	109.5	C20B—C19B—C24B	117.81 (13)
C20A—C19A—C24A	117.60 (13)	C20B—C19B—C5B	123.66 (12)
C20A—C19A—C5A	124.74 (12)	C24B—C19B—C5B	118.32 (12)
C24A—C19A—C5A	117.66 (12)	C21B—C20B—C19B	118.73 (14)
C21A—C20A—C19A	118.89 (13)	C21B—C20B—H20B	120.6
C21A—C20A—H20A	120.6	C19B—C20B—H20B	120.6
C19A—C20A—H20A	120.6	N22B—C21B—C20B	123.66 (14)
N22A—C21A—C20A	123.72 (14)	N22B—C21B—H21B	118.2
N22A—C21A—H21A	118.1	C20B—C21B—H21B	118.2
C20A—C21A—H21A	118.1	C21B—N22B—C23B	117.17 (13)
C23A—N22A—C21A	116.99 (13)	N22B—C23B—C24B	123.65 (14)
N22A—C23A—C24A	123.75 (13)	N22B—C23B—H23B	118.2
N22A—C23A—H23A	118.1	C24B—C23B—H23B	118.2
C24A—C23A—H23A	118.1	C23B—C24B—C19B	118.93 (14)
C23A—C24A—C19A	119.05 (13)	C23B—C24B—H24B	120.5
C23A—C24A—H24A	120.5	C19B—C24B—H24B	120.5
C19A—C24A—H24A	120.5	H25A—O25—H25B	107 (2)
C5B—N1B—N2B	107.69 (11)
C5A—N1A—N2A—C3A	0.04 (16)	C5B—N1B—N2B—C3B	0.47 (16)
N1A—N2A—C3A—N4A	−0.71 (16)	N1B—N2B—C3B—N4B	−0.51 (16)
N1A—N2A—C3A—C6A	176.50 (13)	N1B—N2B—C3B—C6B	179.78 (13)
N2A—C3A—N4A—C5A	1.06 (15)	N2B—C3B—N4B—C5B	0.36 (16)
C6A—C3A—N4A—C5A	−176.14 (13)	C6B—C3B—N4B—C5B	−179.92 (13)
N2A—C3A—N4A—C12A	176.44 (12)	N2B—C3B—N4B—C12B	173.18 (13)
C6A—C3A—N4A—C12A	−0.8 (2)	C6B—C3B—N4B—C12B	−7.1 (2)
N2A—N1A—C5A—N4A	0.63 (16)	N2B—N1B—C5B—N4B	−0.25 (16)
N2A—N1A—C5A—C19A	−176.64 (12)	N2B—N1B—C5B—C19B	175.94 (12)
C3A—N4A—C5A—N1A	−1.02 (15)	C3B—N4B—C5B—N1B	−0.05 (15)
C12A—N4A—C5A—N1A	−176.18 (13)	C12B—N4B—C5B—N1B	−172.62 (13)
C3A—N4A—C5A—C19A	176.06 (13)	C3B—N4B—C5B—C19B	−176.00 (13)
C12A—N4A—C5A—C19A	0.9 (2)	C12B—N4B—C5B—C19B	11.4 (2)
N2A—C3A—C6A—C7A	−47.08 (19)	N2B—C3B—C6B—C7B	−7.6 (2)
N4A—C3A—C6A—C7A	129.72 (14)	N4B—C3B—C6B—C7B	172.73 (13)
C3A—C6A—C7A—C8A	113.07 (16)	C3B—C6B—C7B—C8B	118.41 (16)
C3A—C6A—C7A—C9A	−64.30 (15)	C3B—C6B—C7B—C9B	−67.30 (17)
C8A—C7A—C9A—O10A	−175.09 (15)	C8B—C7B—C9B—O10B	158.02 (15)
C6A—C7A—C9A—O10A	2.37 (19)	C6B—C7B—C9B—O10B	−16.4 (2)
C8A—C7A—C9A—O11A	2.28 (19)	C8B—C7B—C9B—O11B	−21.1 (2)
C6A—C7A—C9A—O11A	179.74 (11)	C6B—C7B—C9B—O11B	164.47 (12)
C3A—N4A—C12A—C17A	−86.66 (17)	C3B—N4B—C12B—C13B	−93.89 (17)
C5A—N4A—C12A—C17A	87.56 (18)	C5B—N4B—C12B—C13B	77.17 (19)
C3A—N4A—C12A—C13A	92.27 (17)	C3B—N4B—C12B—C17B	86.56 (18)
C5A—N4A—C12A—C13A	−93.51 (17)	C5B—N4B—C12B—C17B	−102.38 (17)
C17A—C12A—C13A—C14A	−1.0 (2)	C17B—C12B—C13B—C14B	0.4 (2)
N4A—C12A—C13A—C14A	−179.92 (13)	N4B—C12B—C13B—C14B	−179.14 (13)
C12A—C13A—C14A—C15A	1.4 (2)	C12B—C13B—C14B—C15B	0.5 (2)
C13A—C14A—C15A—C16A	−0.9 (2)	C13B—C14B—C15B—C16B	−0.5 (2)
C13A—C14A—C15A—C18A	179.02 (15)	C13B—C14B—C15B—C18B	178.25 (15)
C14A—C15A—C16A—C17A	0.0 (2)	C14B—C15B—C16B—C17B	−0.3 (2)
C18A—C15A—C16A—C17A	−179.95 (15)	C18B—C15B—C16B—C17B	−179.07 (16)
C13A—C12A—C17A—C16A	0.1 (2)	C13B—C12B—C17B—C16B	−1.2 (2)
N4A—C12A—C17A—C16A	179.02 (13)	N4B—C12B—C17B—C16B	178.34 (13)
C15A—C16A—C17A—C12A	0.4 (2)	C15B—C16B—C17B—C12B	1.2 (2)
N1A—C5A—C19A—C20A	−159.06 (14)	N1B—C5B—C19B—C20B	−151.82 (15)
N4A—C5A—C19A—C20A	24.2 (2)	N4B—C5B—C19B—C20B	23.7 (2)
N1A—C5A—C19A—C24A	20.3 (2)	N1B—C5B—C19B—C24B	22.8 (2)
N4A—C5A—C19A—C24A	−156.40 (14)	N4B—C5B—C19B—C24B	−161.69 (14)
C24A—C19A—C20A—C21A	0.1 (2)	C24B—C19B—C20B—C21B	−1.8 (2)
C5A—C19A—C20A—C21A	179.52 (14)	C5B—C19B—C20B—C21B	172.90 (14)
C19A—C20A—C21A—N22A	0.5 (2)	C19B—C20B—C21B—N22B	−0.3 (2)
C20A—C21A—N22A—C23A	−0.8 (2)	C20B—C21B—N22B—C23B	1.6 (2)
C21A—N22A—C23A—C24A	0.5 (2)	C21B—N22B—C23B—C24B	−0.8 (2)
N22A—C23A—C24A—C19A	0.1 (2)	N22B—C23B—C24B—C19B	−1.3 (2)
C20A—C19A—C24A—C23A	−0.4 (2)	C20B—C19B—C24B—C23B	2.5 (2)
C5A—C19A—C24A—C23A	−179.87 (13)	C5B—C19B—C24B—C23B	−172.47 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O11A—H11A···N22Ai	0.92 (3)	1.77 (3)	2.6838 (17)	178 (2)
O11B—H11B···O25	0.98 (2)	1.59 (2)	2.5619 (16)	174 (2)
O25—H25A···N1A	0.86 (2)	2.00 (2)	2.8373 (17)	166 (2)
O25—H25B···N22Bii	0.94 (2)	1.87 (2)	2.8050 (18)	171 (2)
C6A—H6A2···O10Biii	0.97	2.51	3.3300 (18)	142
C24A—H24A···O10Biv	0.93	2.41	3.2683 (18)	153
C24B—H24B···O10Aiii	0.93	2.57	3.4628 (18)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O11A—H11A⋯N22A i	0.92 (3)	1.77 (3)	2.6838 (17)	178 (2)
O11B—H11B⋯O25	0.98 (2)	1.59 (2)	2.5619 (16)	174 (2)
O25—H25A⋯N1A	0.86 (2)	2.00 (2)	2.8373 (17)	166 (2)
O25—H25B⋯N22B ii	0.94 (2)	1.87 (2)	2.8050 (18)	171 (2)
C6A—H6A2⋯O10B iii	0.97	2.51	3.3300 (18)	142
C24A—H24A⋯O10B iv	0.93	2.41	3.2683 (18)	153
C24B—H24B⋯O10A iii	0.93	2.57	3.4628 (18)	162

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