1-(2-Benzoyl-1-phenyl-eth-yl)-4-[(2-hy-droxy-1-naphth-yl)methyl-idene-amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione.

In the title compound, C(29)H(24)N(4)O(2)S, intra-molecular O-H⋯N hydrogen bonding influences the mol-ecular conform-ation; the naphthol system and triazole ring form a dihedral angle of 3.88 (7)°. In the crystal, π-π inter-actions between the five- and six-membered rings of neighbouring mol-ecules [centroid-centroid distances = 3.541 (3) and 3.711 (3) Å] consolidate the crystal packing.

Related literature

For details of the pharmacological properties of Mannich bases, see: Joshi et al. (2004 ▶); Ferlin et al. (2002 ▶); Holla et al. (2003 ▶). For their application in the polymer indusry, see: Negm et al. (2005 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C29H24N4O2S

M = 492.58

Monoclinic,

a = 7.8192 (16) Å

b = 20.248 (4) Å

c = 15.360 (3) Å

β = 94.69 (3)°

V = 2423.7 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.17 mm−1

T = 153 K

0.18 × 0.16 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.970, T max = 0.983

23596 measured reflections

5746 independent reflections

4491 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.127

S = 0.96

5746 reflections

331 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810052979/cv5020sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052979/cv5020Isup2.hkl

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

C29H24N4O2S	F(000) = 1032
Mr = 492.58	Dx = 1.350 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6032 reflections
a = 7.8192 (16) Å	θ = 1.7–27.9°
b = 20.248 (4) Å	µ = 0.17 mm−1
c = 15.360 (3) Å	T = 153 K
β = 94.69 (3)°	Prism, colourless
V = 2423.7 (8) Å3	0.18 × 0.16 × 0.10 mm
Z = 4

Rigaku Saturn CCD area-detector diffractometer	5746 independent reflections
Radiation source: rotating anode	4491 reflections with I > 2σ(I)
multilayer	Rint = 0.048
Detector resolution: 7.31 pixels mm-1	θmax = 27.9°, θmin = 1.7°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −26→26
Tmin = 0.970, Tmax = 0.983	l = −17→20
23596 measured reflections

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)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.127	w = 1/[σ2(Fo2) + (0.06P)2 + 1.1394P] where P = (Fo2 + 2Fc2)/3
S = 0.96	(Δ/σ)max = 0.001
5746 reflections	Δρmax = 0.31 e Å−3
331 parameters	Δρmin = −0.30 e Å−3
3 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0261 (17)

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
S1	0.28857 (5)	0.20831 (2)	−0.04504 (3)	0.02895 (15)
O1	0.77192 (16)	−0.01503 (7)	−0.07589 (10)	0.0358 (3)
H1	0.760 (3)	0.0246 (14)	−0.0519 (16)	0.071 (9)*
O2	0.64680 (17)	0.36195 (7)	−0.03561 (8)	0.0396 (4)
N1	0.61510 (18)	0.09480 (7)	−0.04258 (9)	0.0249 (3)
N2	0.60991 (17)	0.15359 (7)	0.00352 (9)	0.0210 (3)
N3	0.55703 (17)	0.24391 (7)	0.06788 (9)	0.0227 (3)
N4	0.72369 (17)	0.22717 (7)	0.09686 (9)	0.0249 (3)
C1	0.4776 (2)	0.07206 (9)	−0.08296 (11)	0.0246 (4)
H1A	0.3737	0.0963	−0.0827	0.030*
C2	0.4795 (2)	0.00970 (8)	−0.12901 (11)	0.0237 (4)
C3	0.3266 (2)	−0.01202 (9)	−0.17983 (11)	0.0252 (4)
C4	0.1714 (2)	0.02452 (9)	−0.18680 (12)	0.0288 (4)
H4	0.1656	0.0655	−0.1570	0.035*
C5	0.0298 (3)	0.00162 (10)	−0.23590 (12)	0.0351 (5)
H5	−0.0730	0.0269	−0.2393	0.042*
C6	0.0336 (3)	−0.05847 (11)	−0.28135 (12)	0.0401 (5)
H6	−0.0655	−0.0736	−0.3155	0.048*
C7	0.1806 (3)	−0.09494 (10)	−0.27597 (12)	0.0374 (5)
H7	0.1831	−0.1357	−0.3065	0.045*
C8	0.3299 (2)	−0.07301 (9)	−0.22563 (11)	0.0310 (4)
C9	0.4830 (3)	−0.11108 (9)	−0.21919 (12)	0.0350 (5)
H9	0.4860	−0.1515	−0.2505	0.042*
C10	0.6248 (3)	−0.09121 (9)	−0.16955 (13)	0.0340 (5)
H10	0.7247	−0.1181	−0.1654	0.041*
C11	0.6248 (2)	−0.03069 (9)	−0.12387 (11)	0.0280 (4)
C12	0.4817 (2)	0.20104 (8)	0.00885 (11)	0.0218 (4)
C13	0.7525 (2)	0.17231 (9)	0.05596 (11)	0.0228 (4)
C14	0.9162 (2)	0.13542 (9)	0.06260 (12)	0.0287 (4)
H14A	0.9996	0.1582	0.1032	0.043*
H14B	0.9607	0.1329	0.0049	0.043*
H14C	0.8968	0.0907	0.0841	0.043*
C15	0.4795 (2)	0.30482 (8)	0.09933 (11)	0.0250 (4)
H15	0.3971	0.3220	0.0515	0.030*
C16	0.3790 (2)	0.29017 (8)	0.17815 (11)	0.0246 (4)
C17	0.2021 (2)	0.28203 (9)	0.16602 (12)	0.0304 (4)
H17	0.1450	0.2880	0.1096	0.037*
C18	0.1083 (2)	0.26531 (10)	0.23552 (13)	0.0343 (5)
H18	−0.0125	0.2598	0.2264	0.041*
C19	0.1902 (2)	0.25662 (10)	0.31833 (13)	0.0350 (5)
H19	0.1264	0.2444	0.3658	0.042*
C20	0.3654 (2)	0.26592 (10)	0.33109 (12)	0.0329 (4)
H20	0.4217	0.2607	0.3878	0.039*
C21	0.4598 (2)	0.28280 (9)	0.26172 (12)	0.0297 (4)
H21	0.5802	0.2894	0.2713	0.036*
C22	0.6197 (2)	0.35606 (9)	0.11750 (11)	0.0282 (4)
H22A	0.5679	0.3971	0.1386	0.034*
H22B	0.7029	0.3396	0.1645	0.034*
C23	0.7142 (2)	0.37200 (9)	0.03791 (12)	0.0292 (4)
C24	0.8901 (2)	0.39992 (8)	0.05155 (11)	0.0267 (4)
C25	0.9478 (2)	0.42988 (9)	0.13012 (12)	0.0313 (4)
H25	0.8764	0.4305	0.1773	0.038*
C26	1.1086 (2)	0.45870 (10)	0.13988 (12)	0.0343 (5)
H26	1.1462	0.4801	0.1931	0.041*
C27	1.2149 (2)	0.45643 (10)	0.07221 (13)	0.0339 (4)
H27	1.3257	0.4760	0.0790	0.041*
C28	1.1596 (2)	0.42573 (10)	−0.00498 (13)	0.0356 (5)
H28	1.2336	0.4235	−0.0509	0.043*
C29	0.9982 (2)	0.39815 (9)	−0.01643 (12)	0.0332 (4)
H29	0.9606	0.3780	−0.0705	0.040*

	U11	U22	U33	U12	U13	U23
S1	0.0224 (3)	0.0312 (3)	0.0323 (3)	0.00355 (18)	−0.00375 (19)	−0.00608 (19)
O1	0.0287 (8)	0.0362 (8)	0.0423 (8)	0.0057 (6)	0.0020 (6)	−0.0040 (7)
O2	0.0469 (8)	0.0435 (9)	0.0273 (8)	−0.0095 (7)	−0.0036 (6)	0.0027 (6)
N1	0.0272 (8)	0.0238 (8)	0.0241 (8)	0.0011 (6)	0.0048 (6)	−0.0021 (6)
N2	0.0205 (7)	0.0225 (7)	0.0203 (7)	0.0015 (6)	0.0026 (6)	−0.0005 (5)
N3	0.0197 (7)	0.0238 (7)	0.0241 (8)	0.0012 (6)	−0.0013 (6)	−0.0012 (6)
N4	0.0200 (7)	0.0269 (8)	0.0273 (8)	0.0017 (6)	−0.0018 (6)	0.0015 (6)
C1	0.0253 (9)	0.0251 (9)	0.0238 (9)	0.0022 (7)	0.0037 (7)	0.0000 (7)
C2	0.0283 (9)	0.0220 (8)	0.0216 (9)	0.0004 (7)	0.0065 (7)	0.0022 (7)
C3	0.0316 (10)	0.0252 (9)	0.0194 (9)	−0.0038 (7)	0.0069 (7)	0.0012 (7)
C4	0.0320 (10)	0.0292 (9)	0.0253 (9)	−0.0031 (8)	0.0025 (8)	0.0015 (7)
C5	0.0347 (11)	0.0413 (11)	0.0284 (10)	−0.0054 (9)	−0.0017 (8)	0.0047 (8)
C6	0.0463 (13)	0.0472 (13)	0.0260 (10)	−0.0173 (10)	−0.0031 (9)	0.0020 (9)
C7	0.0547 (13)	0.0327 (11)	0.0252 (10)	−0.0127 (10)	0.0052 (9)	−0.0018 (8)
C8	0.0441 (12)	0.0273 (9)	0.0228 (9)	−0.0063 (8)	0.0094 (8)	0.0015 (7)
C9	0.0551 (13)	0.0219 (9)	0.0298 (10)	0.0003 (9)	0.0151 (9)	−0.0016 (7)
C10	0.0409 (11)	0.0252 (9)	0.0374 (11)	0.0073 (8)	0.0121 (9)	0.0006 (8)
C11	0.0316 (10)	0.0273 (9)	0.0260 (9)	0.0021 (8)	0.0088 (8)	0.0034 (7)
C12	0.0206 (9)	0.0230 (8)	0.0222 (9)	−0.0010 (7)	0.0037 (7)	−0.0003 (7)
C13	0.0207 (8)	0.0256 (9)	0.0223 (9)	−0.0023 (7)	0.0019 (7)	0.0033 (7)
C14	0.0220 (9)	0.0307 (10)	0.0332 (10)	0.0021 (8)	0.0010 (7)	0.0031 (8)
C15	0.0257 (9)	0.0224 (9)	0.0265 (9)	0.0034 (7)	0.0005 (7)	−0.0020 (7)
C16	0.0276 (9)	0.0201 (8)	0.0260 (9)	0.0029 (7)	0.0012 (7)	−0.0030 (7)
C17	0.0287 (10)	0.0328 (10)	0.0291 (10)	0.0024 (8)	−0.0015 (8)	−0.0029 (8)
C18	0.0266 (10)	0.0385 (11)	0.0383 (11)	0.0007 (8)	0.0059 (8)	−0.0059 (9)
C19	0.0383 (11)	0.0366 (11)	0.0312 (11)	−0.0004 (9)	0.0103 (9)	−0.0065 (8)
C20	0.0379 (11)	0.0353 (11)	0.0252 (10)	0.0014 (9)	0.0016 (8)	−0.0040 (8)
C21	0.0287 (10)	0.0304 (10)	0.0297 (10)	0.0011 (8)	0.0003 (8)	−0.0050 (8)
C22	0.0321 (10)	0.0252 (9)	0.0270 (10)	−0.0006 (8)	0.0005 (8)	−0.0038 (7)
C23	0.0381 (11)	0.0226 (9)	0.0263 (10)	0.0009 (8)	−0.0002 (8)	0.0015 (7)
C24	0.0332 (10)	0.0199 (8)	0.0271 (9)	0.0015 (7)	0.0038 (8)	0.0015 (7)
C25	0.0342 (10)	0.0316 (10)	0.0284 (10)	0.0008 (8)	0.0055 (8)	−0.0037 (8)
C26	0.0354 (11)	0.0331 (10)	0.0342 (11)	−0.0013 (9)	0.0008 (8)	−0.0050 (8)
C27	0.0309 (10)	0.0299 (10)	0.0417 (11)	0.0006 (8)	0.0064 (8)	0.0041 (8)
C28	0.0388 (11)	0.0369 (11)	0.0328 (11)	0.0050 (9)	0.0129 (9)	0.0045 (9)
C29	0.0430 (11)	0.0313 (10)	0.0252 (10)	0.0011 (9)	0.0032 (8)	0.0006 (8)

S1—C12	1.6679 (18)	C14—H14A	0.9800
O1—C11	1.352 (2)	C14—H14B	0.9800
O1—H1	0.89 (3)	C14—H14C	0.9800
O2—C23	1.223 (2)	C15—C22	1.518 (2)
N1—C1	1.282 (2)	C15—C16	1.526 (2)
N1—N2	1.3873 (19)	C15—H15	1.0000
N2—C13	1.374 (2)	C16—C17	1.390 (2)
N2—C12	1.396 (2)	C16—C21	1.392 (3)
N3—C12	1.355 (2)	C17—C18	1.386 (3)
N3—N4	1.3842 (19)	C17—H17	0.9500
N3—C15	1.473 (2)	C18—C19	1.388 (3)
N4—C13	1.305 (2)	C18—H18	0.9500
C1—C2	1.448 (2)	C19—C20	1.380 (3)
C1—H1A	0.9500	C19—H19	0.9500
C2—C11	1.397 (2)	C20—C21	1.388 (2)
C2—C3	1.442 (2)	C20—H20	0.9500
C3—C4	1.418 (2)	C21—H21	0.9500
C3—C8	1.423 (2)	C22—C23	1.514 (2)
C4—C5	1.369 (3)	C22—H22A	0.9900
C4—H4	0.9500	C22—H22B	0.9900
C5—C6	1.404 (3)	C23—C24	1.486 (2)
C5—H5	0.9500	C24—C25	1.393 (2)
C6—C7	1.363 (3)	C24—C29	1.397 (2)
C6—H6	0.9500	C25—C26	1.383 (3)
C7—C8	1.417 (3)	C25—H25	0.9500
C7—H7	0.9500	C26—C27	1.384 (3)
C8—C9	1.421 (3)	C26—H26	0.9500
C9—C10	1.354 (3)	C27—C28	1.377 (3)
C9—H9	0.9500	C27—H27	0.9500
C10—C11	1.412 (2)	C28—C29	1.378 (3)
C10—H10	0.9500	C28—H28	0.9500
C13—C14	1.478 (2)	C29—H29	0.9500
Cg1···Cg1i	3.541 (3)	Cg2···Cg3ii	3.711 (3)
C11—O1—H1	109.0 (16)	H14B—C14—H14C	109.5
C1—N1—N2	119.78 (14)	N3—C15—C22	108.79 (13)
C13—N2—N1	118.65 (13)	N3—C15—C16	110.50 (14)
C13—N2—C12	109.15 (14)	C22—C15—C16	113.46 (14)
N1—N2—C12	132.19 (14)	N3—C15—H15	108.0
C12—N3—N4	113.88 (14)	C22—C15—H15	108.0
C12—N3—C15	125.99 (14)	C16—C15—H15	108.0
N4—N3—C15	120.09 (13)	C17—C16—C21	118.86 (16)
C13—N4—N3	104.41 (13)	C17—C16—C15	119.23 (15)
N1—C1—C2	120.53 (16)	C21—C16—C15	121.88 (16)
N1—C1—H1A	119.7	C18—C17—C16	120.61 (17)
C2—C1—H1A	119.7	C18—C17—H17	119.7
C11—C2—C3	119.12 (16)	C16—C17—H17	119.7
C11—C2—C1	121.57 (16)	C17—C18—C19	120.22 (18)
C3—C2—C1	119.30 (15)	C17—C18—H18	119.9
C4—C3—C8	117.74 (16)	C19—C18—H18	119.9
C4—C3—C2	123.25 (16)	C20—C19—C18	119.41 (18)
C8—C3—C2	119.01 (16)	C20—C19—H19	120.3
C5—C4—C3	120.92 (18)	C18—C19—H19	120.3
C5—C4—H4	119.5	C19—C20—C21	120.57 (18)
C3—C4—H4	119.5	C19—C20—H20	119.7
C4—C5—C6	121.22 (19)	C21—C20—H20	119.7
C4—C5—H5	119.4	C20—C21—C16	120.30 (17)
C6—C5—H5	119.4	C20—C21—H21	119.8
C7—C6—C5	119.41 (19)	C16—C21—H21	119.8
C7—C6—H6	120.3	C23—C22—C15	112.96 (14)
C5—C6—H6	120.3	C23—C22—H22A	109.0
C6—C7—C8	121.07 (19)	C15—C22—H22A	109.0
C6—C7—H7	119.5	C23—C22—H22B	109.0
C8—C7—H7	119.5	C15—C22—H22B	109.0
C7—C8—C9	121.31 (18)	H22A—C22—H22B	107.8
C7—C8—C3	119.64 (18)	O2—C23—C24	121.14 (16)
C9—C8—C3	119.05 (17)	O2—C23—C22	120.53 (16)
C10—C9—C8	121.64 (18)	C24—C23—C22	118.33 (15)
C10—C9—H9	119.2	C25—C24—C29	119.08 (17)
C8—C9—H9	119.2	C25—C24—C23	121.24 (16)
C9—C10—C11	120.27 (18)	C29—C24—C23	119.65 (16)
C9—C10—H10	119.9	C26—C25—C24	120.33 (17)
C11—C10—H10	119.9	C26—C25—H25	119.8
O1—C11—C2	123.05 (17)	C24—C25—H25	119.8
O1—C11—C10	116.08 (16)	C25—C26—C27	120.08 (18)
C2—C11—C10	120.87 (17)	C25—C26—H26	120.0
N3—C12—N2	101.83 (14)	C27—C26—H26	120.0
N3—C12—S1	127.02 (13)	C28—C27—C26	119.75 (18)
N2—C12—S1	131.07 (13)	C28—C27—H27	120.1
N4—C13—N2	110.67 (15)	C26—C27—H27	120.1
N4—C13—C14	125.43 (16)	C27—C28—C29	120.85 (17)
N2—C13—C14	123.88 (16)	C27—C28—H28	119.6
C13—C14—H14A	109.5	C29—C28—H28	119.6
C13—C14—H14B	109.5	C28—C29—C24	119.88 (17)
H14A—C14—H14B	109.5	C28—C29—H29	120.1
C13—C14—H14C	109.5	C24—C29—H29	120.1
H14A—C14—H14C	109.5
C1—N1—N2—C13	171.14 (15)	N3—N4—C13—N2	−0.84 (18)
C1—N1—N2—C12	−8.5 (3)	N3—N4—C13—C14	177.86 (15)
C12—N3—N4—C13	−0.75 (19)	N1—N2—C13—N4	−177.60 (14)
C15—N3—N4—C13	−178.93 (14)	C12—N2—C13—N4	2.09 (19)
N2—N1—C1—C2	−177.96 (14)	N1—N2—C13—C14	3.7 (2)
N1—C1—C2—C11	6.5 (3)	C12—N2—C13—C14	−176.63 (15)
N1—C1—C2—C3	−174.89 (15)	C12—N3—C15—C22	−146.60 (16)
C11—C2—C3—C4	178.02 (15)	N4—N3—C15—C22	31.3 (2)
C1—C2—C3—C4	−0.6 (2)	C12—N3—C15—C16	88.2 (2)
C11—C2—C3—C8	−2.0 (2)	N4—N3—C15—C16	−93.84 (17)
C1—C2—C3—C8	179.36 (15)	N3—C15—C16—C17	−98.27 (18)
C8—C3—C4—C5	0.1 (2)	C22—C15—C16—C17	139.25 (17)
C2—C3—C4—C5	−179.94 (16)	N3—C15—C16—C21	79.84 (19)
C3—C4—C5—C6	−0.4 (3)	C22—C15—C16—C21	−42.6 (2)
C4—C5—C6—C7	0.5 (3)	C21—C16—C17—C18	−1.5 (3)
C5—C6—C7—C8	−0.3 (3)	C15—C16—C17—C18	176.63 (17)
C6—C7—C8—C9	179.46 (17)	C16—C17—C18—C19	0.1 (3)
C6—C7—C8—C3	0.0 (3)	C17—C18—C19—C20	1.1 (3)
C4—C3—C8—C7	0.1 (2)	C18—C19—C20—C21	−1.0 (3)
C2—C3—C8—C7	−179.90 (15)	C19—C20—C21—C16	−0.4 (3)
C4—C3—C8—C9	−179.36 (15)	C17—C16—C21—C20	1.7 (3)
C2—C3—C8—C9	0.7 (2)	C15—C16—C21—C20	−176.46 (16)
C7—C8—C9—C10	−178.40 (17)	N3—C15—C22—C23	58.68 (19)
C3—C8—C9—C10	1.0 (3)	C16—C15—C22—C23	−177.89 (14)
C8—C9—C10—C11	−1.3 (3)	C15—C22—C23—O2	22.8 (2)
C3—C2—C11—O1	−178.19 (15)	C15—C22—C23—C24	−157.10 (15)
C1—C2—C11—O1	0.4 (3)	O2—C23—C24—C25	160.25 (18)
C3—C2—C11—C10	1.7 (2)	C22—C23—C24—C25	−19.9 (2)
C1—C2—C11—C10	−179.67 (16)	O2—C23—C24—C29	−17.6 (3)
C9—C10—C11—O1	179.87 (16)	C22—C23—C24—C29	162.27 (17)
C9—C10—C11—C2	−0.1 (3)	C29—C24—C25—C26	1.4 (3)
N4—N3—C12—N2	1.92 (18)	C23—C24—C25—C26	−176.53 (17)
C15—N3—C12—N2	179.96 (14)	C24—C25—C26—C27	−1.6 (3)
N4—N3—C12—S1	−175.26 (12)	C25—C26—C27—C28	0.4 (3)
C15—N3—C12—S1	2.8 (2)	C26—C27—C28—C29	1.2 (3)
C13—N2—C12—N3	−2.33 (17)	C27—C28—C29—C24	−1.4 (3)
N1—N2—C12—N3	177.30 (15)	C25—C24—C29—C28	0.1 (3)
C13—N2—C12—S1	174.67 (13)	C23—C24—C29—C28	178.06 (17)
N1—N2—C12—S1	−5.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.89 (3)	1.83 (3)	2.610 (2)	145 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.89 (3)	1.83 (3)	2.610 (2)	145 (2)