rac-3-{4-[(2-Hy-droxy-benzyl-idene)amino]-3-phenyl-5-sulfanyl-idene-4,5-dihydro-1H-1,2,4-triazol-1-yl}-1,3-diphenyl-propan-1-one.

In the title compound, C(30)H(24)N(4)O(2)S, the four phenyl rings of the substituent groups make dihedral angles of 88.1 (2), 81.0 (2), 21.4 (2) and 44.6 (2)° with the triazole group. An intra-molecular hy-droxy-imino O-H⋯N hydrogen bond results in the formation of an approximately planar (r.m.s deviation = 0.0230 Å) six-membered ring.

Related literature

For the crystal structures of related 1,2,4-triazole-5(4H)-thione derivatives, see: Al-Tamimi et al. (2010 ▶); Fun et al. (2009 ▶); Gao et al. (2011 ▶); Tan et al. (2010 ▶); Wang et al. (2011 ▶); Zhao et al. (2010 ▶).

Experimental

Crystal data

C30H24N4O2S

M = 504.59

Triclinic,

a = 6.770 (2) Å

b = 13.170 (5) Å

c = 14.851 (5) Å

α = 78.114 (12)°

β = 81.715 (15)°

γ = 87.318 (16)°

V = 1282.0 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.16 mm−1

T = 113 K

0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.968, T max = 0.981

16609 measured reflections

6076 independent reflections

3749 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.094

S = 0.95

6076 reflections

338 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.21 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 datablock(s) global, I. DOI: 10.1107/S1600536811035203/zs2139sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035203/zs2139Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811035203/zs2139Isup3.cml

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

C30H24N4O2S	Z = 2
Mr = 504.59	F(000) = 528
Triclinic, P1	Dx = 1.307 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.770 (2) Å	Cell parameters from 4176 reflections
b = 13.170 (5) Å	θ = 1.4–28.1°
c = 14.851 (5) Å	µ = 0.16 mm−1
α = 78.114 (12)°	T = 113 K
β = 81.715 (15)°	Prism, colorless
γ = 87.318 (16)°	0.20 × 0.18 × 0.12 mm
V = 1282.0 (7) Å3

Rigaku Saturn CCD area-detector diffractometer	6076 independent reflections
Radiation source: rotating anode	3749 reflections with I > 2σ(I)
multilayer	Rint = 0.043
Detector resolution: 14.63 pixels mm-1	θmax = 27.9°, θmin = 1.4°
φ and ω scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −17→17
Tmin = 0.968, Tmax = 0.981	l = −18→19
16609 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ2(Fo2) + (0.0415P)2] where P = (Fo2 + 2Fc2)/3
6076 reflections	(Δ/σ)max = 0.001
338 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.21 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
S1	1.23731 (6)	0.74106 (3)	0.66002 (2)	0.02837 (11)
O1	1.1833 (2)	0.82091 (11)	0.92569 (8)	0.0578 (4)
O2	0.83353 (15)	0.41453 (9)	0.60325 (8)	0.0347 (3)
H2	0.828 (3)	0.470 (2)	0.6402 (16)	0.113 (9)*
N1	0.75550 (17)	0.71629 (9)	0.84047 (8)	0.0248 (3)
N2	0.92480 (17)	0.76425 (9)	0.79086 (7)	0.0227 (3)
N3	0.92676 (16)	0.61510 (9)	0.75493 (7)	0.0212 (3)
N4	0.95198 (17)	0.53608 (9)	0.70367 (7)	0.0224 (3)
C1	1.0334 (2)	0.70663 (11)	0.73499 (9)	0.0223 (3)
C2	0.7565 (2)	0.62593 (11)	0.81636 (9)	0.0218 (3)
C3	0.9499 (2)	0.87572 (11)	0.78459 (9)	0.0233 (3)
H3	1.0950	0.8915	0.7666	0.028*
C4	0.8830 (2)	0.90266 (11)	0.87934 (9)	0.0282 (3)
H4A	0.8801	0.9790	0.8728	0.034*
H4B	0.7457	0.8776	0.9023	0.034*
C5	1.0196 (3)	0.85503 (12)	0.95006 (11)	0.0355 (4)
C6	0.9467 (3)	0.85086 (12)	1.05085 (10)	0.0382 (4)
C7	0.7628 (3)	0.89039 (14)	1.08254 (11)	0.0455 (5)
H7	0.6782	0.9243	1.0394	0.055*
C8	0.7012 (3)	0.88071 (16)	1.17744 (12)	0.0597 (6)
H8	0.5743	0.9072	1.1993	0.072*
C9	0.8262 (4)	0.83231 (17)	1.23954 (13)	0.0711 (7)
H9	0.7835	0.8245	1.3043	0.085*
C10	1.0123 (4)	0.79515 (16)	1.20885 (13)	0.0680 (7)
H10	1.0989	0.7638	1.2521	0.082*
C11	1.0712 (3)	0.80400 (13)	1.11513 (11)	0.0518 (5)
H11	1.1986	0.7778	1.0938	0.062*
C12	0.8368 (2)	0.93823 (11)	0.71014 (9)	0.0240 (3)
C13	0.6371 (2)	0.92297 (14)	0.70853 (11)	0.0398 (4)
H13	0.5671	0.8718	0.7553	0.048*
C14	0.5375 (3)	0.98140 (14)	0.63950 (12)	0.0455 (5)
H14	0.4007	0.9690	0.6389	0.055*
C15	0.6345 (3)	1.05683 (13)	0.57213 (11)	0.0400 (4)
H15	0.5645	1.0986	0.5264	0.048*
C16	0.8329 (3)	1.07093 (14)	0.57177 (12)	0.0521 (5)
H16	0.9025	1.1215	0.5243	0.062*
C17	0.9338 (3)	1.01215 (14)	0.64007 (11)	0.0447 (5)
H17	1.0721	1.0229	0.6386	0.054*
C18	0.5920 (2)	0.55264 (11)	0.84967 (9)	0.0232 (3)
C19	0.6105 (2)	0.44711 (12)	0.84903 (10)	0.0325 (4)
H19	0.7353	0.4187	0.8268	0.039*
C20	0.4476 (2)	0.38335 (13)	0.88066 (11)	0.0381 (4)
H20	0.4609	0.3115	0.8794	0.046*
C21	0.2664 (2)	0.42313 (13)	0.91398 (10)	0.0350 (4)
H21	0.1550	0.3791	0.9356	0.042*
C22	0.2481 (2)	0.52800 (13)	0.91564 (10)	0.0318 (4)
H22	0.1237	0.5556	0.9392	0.038*
C23	0.4081 (2)	0.59262 (12)	0.88353 (9)	0.0267 (3)
H23	0.3933	0.6645	0.8844	0.032*
C24	1.1334 (2)	0.50562 (11)	0.68280 (9)	0.0227 (3)
H24	1.2383	0.5311	0.7077	0.027*
C25	1.1778 (2)	0.43255 (11)	0.62150 (9)	0.0221 (3)
C26	1.0299 (2)	0.39283 (11)	0.58138 (10)	0.0241 (3)
C27	1.0835 (2)	0.32828 (12)	0.51852 (10)	0.0300 (4)
H27	0.9836	0.3018	0.4912	0.036*
C28	1.2809 (2)	0.30257 (12)	0.49579 (10)	0.0338 (4)
H28	1.3162	0.2587	0.4524	0.041*
C29	1.4298 (2)	0.33974 (13)	0.53524 (11)	0.0358 (4)
H29	1.5658	0.3209	0.5198	0.043*
C30	1.3763 (2)	0.40458 (12)	0.59726 (10)	0.0303 (4)
H30	1.4773	0.4308	0.6240	0.036*

	U11	U22	U33	U12	U13	U23
S1	0.0274 (2)	0.0312 (2)	0.0263 (2)	−0.00792 (17)	0.00275 (16)	−0.00803 (16)
O1	0.0705 (9)	0.0658 (10)	0.0453 (8)	0.0350 (8)	−0.0258 (7)	−0.0258 (7)
O2	0.0215 (6)	0.0371 (7)	0.0515 (7)	0.0004 (5)	−0.0089 (5)	−0.0206 (6)
N1	0.0280 (7)	0.0198 (6)	0.0251 (6)	−0.0032 (5)	0.0028 (5)	−0.0047 (5)
N2	0.0278 (7)	0.0175 (6)	0.0221 (6)	−0.0035 (5)	0.0009 (5)	−0.0047 (5)
N3	0.0226 (7)	0.0191 (6)	0.0225 (6)	−0.0021 (5)	0.0007 (5)	−0.0078 (5)
N4	0.0251 (7)	0.0198 (6)	0.0236 (6)	−0.0014 (5)	0.0000 (5)	−0.0096 (5)
C1	0.0259 (8)	0.0215 (8)	0.0205 (7)	−0.0013 (6)	−0.0057 (6)	−0.0049 (6)
C2	0.0240 (8)	0.0194 (7)	0.0207 (7)	0.0012 (6)	0.0005 (6)	−0.0040 (6)
C3	0.0277 (8)	0.0173 (7)	0.0253 (8)	−0.0048 (6)	−0.0026 (6)	−0.0047 (6)
C4	0.0402 (9)	0.0197 (8)	0.0260 (8)	0.0002 (7)	−0.0060 (7)	−0.0072 (6)
C5	0.0568 (12)	0.0214 (8)	0.0319 (9)	0.0065 (8)	−0.0132 (8)	−0.0101 (7)
C6	0.0720 (13)	0.0184 (8)	0.0267 (9)	−0.0022 (8)	−0.0124 (9)	−0.0060 (7)
C7	0.0737 (14)	0.0363 (10)	0.0284 (9)	−0.0090 (10)	−0.0047 (9)	−0.0107 (8)
C8	0.0915 (17)	0.0539 (13)	0.0347 (11)	−0.0183 (12)	0.0057 (11)	−0.0172 (10)
C9	0.137 (2)	0.0507 (14)	0.0249 (10)	−0.0321 (15)	−0.0065 (13)	−0.0031 (10)
C10	0.132 (2)	0.0381 (12)	0.0351 (11)	−0.0064 (14)	−0.0262 (13)	0.0014 (9)
C11	0.0972 (16)	0.0258 (10)	0.0354 (10)	0.0024 (10)	−0.0230 (10)	−0.0042 (8)
C12	0.0305 (9)	0.0191 (7)	0.0238 (7)	−0.0030 (6)	−0.0042 (6)	−0.0067 (6)
C13	0.0358 (10)	0.0415 (11)	0.0363 (9)	−0.0082 (8)	−0.0037 (8)	0.0066 (8)
C14	0.0349 (10)	0.0502 (12)	0.0492 (11)	−0.0031 (9)	−0.0146 (8)	0.0018 (9)
C15	0.0531 (12)	0.0288 (9)	0.0403 (10)	0.0004 (8)	−0.0211 (9)	−0.0020 (8)
C16	0.0608 (13)	0.0387 (11)	0.0505 (11)	−0.0201 (10)	−0.0215 (10)	0.0191 (9)
C17	0.0413 (11)	0.0404 (11)	0.0488 (11)	−0.0176 (9)	−0.0163 (9)	0.0102 (9)
C18	0.0278 (8)	0.0205 (8)	0.0205 (7)	−0.0030 (6)	−0.0005 (6)	−0.0036 (6)
C19	0.0320 (9)	0.0239 (8)	0.0378 (9)	−0.0032 (7)	0.0070 (7)	−0.0051 (7)
C20	0.0455 (11)	0.0235 (9)	0.0433 (10)	−0.0108 (8)	0.0063 (8)	−0.0082 (7)
C21	0.0347 (10)	0.0381 (10)	0.0300 (9)	−0.0178 (8)	0.0036 (7)	−0.0037 (7)
C22	0.0268 (9)	0.0382 (10)	0.0283 (8)	−0.0036 (7)	0.0030 (7)	−0.0058 (7)
C23	0.0283 (9)	0.0254 (8)	0.0252 (8)	−0.0012 (7)	0.0002 (6)	−0.0048 (6)
C24	0.0224 (8)	0.0233 (8)	0.0232 (7)	−0.0013 (6)	−0.0033 (6)	−0.0061 (6)
C25	0.0220 (8)	0.0226 (8)	0.0220 (7)	−0.0013 (6)	−0.0005 (6)	−0.0067 (6)
C26	0.0222 (8)	0.0237 (8)	0.0267 (8)	−0.0010 (6)	−0.0033 (6)	−0.0057 (6)
C27	0.0351 (9)	0.0273 (9)	0.0314 (8)	−0.0008 (7)	−0.0103 (7)	−0.0110 (7)
C28	0.0414 (10)	0.0326 (9)	0.0296 (8)	0.0026 (8)	−0.0004 (7)	−0.0150 (7)
C29	0.0253 (9)	0.0417 (10)	0.0428 (10)	0.0041 (8)	0.0012 (7)	−0.0193 (8)
C30	0.0223 (8)	0.0345 (9)	0.0370 (9)	−0.0011 (7)	−0.0041 (7)	−0.0136 (7)

S1—C1	1.6608 (15)	C13—C14	1.387 (2)
O1—C5	1.2104 (19)	C13—H13	0.9500
O2—C26	1.3538 (17)	C14—C15	1.371 (2)
O2—H2	1.00 (2)	C14—H14	0.9500
N1—C2	1.3110 (17)	C15—C16	1.364 (2)
N1—N2	1.3741 (16)	C15—H15	0.9500
N2—C1	1.3551 (17)	C16—C17	1.386 (2)
N2—C3	1.4681 (18)	C16—H16	0.9500
N3—C2	1.3841 (17)	C17—H17	0.9500
N3—C1	1.3910 (18)	C18—C19	1.392 (2)
N3—N4	1.4015 (15)	C18—C23	1.3958 (19)
N4—C24	1.2890 (17)	C19—C20	1.385 (2)
C2—C18	1.4703 (19)	C19—H19	0.9500
C3—C12	1.516 (2)	C20—C21	1.377 (2)
C3—C4	1.5225 (19)	C20—H20	0.9500
C3—H3	1.0000	C21—C22	1.386 (2)
C4—C5	1.519 (2)	C21—H21	0.9500
C4—H4A	0.9900	C22—C23	1.377 (2)
C4—H4B	0.9900	C22—H22	0.9500
C5—C6	1.498 (2)	C23—H23	0.9500
C6—C7	1.383 (2)	C24—C25	1.4493 (19)
C6—C11	1.394 (2)	C24—H24	0.9500
C7—C8	1.392 (2)	C25—C30	1.3923 (19)
C7—H7	0.9500	C25—C26	1.4076 (19)
C8—C9	1.380 (3)	C26—C27	1.3878 (19)
C8—H8	0.9500	C27—C28	1.375 (2)
C9—C10	1.380 (3)	C27—H27	0.9500
C9—H9	0.9500	C28—C29	1.391 (2)
C10—C11	1.374 (2)	C28—H28	0.9500
C10—H10	0.9500	C29—C30	1.381 (2)
C11—H11	0.9500	C29—H29	0.9500
C12—C13	1.380 (2)	C30—H30	0.9500
C12—C17	1.381 (2)
C26—O2—H2	105.6 (13)	C14—C13—H13	119.6
C2—N1—N2	105.10 (11)	C15—C14—C13	120.74 (16)
C1—N2—N1	113.68 (11)	C15—C14—H14	119.6
C1—N2—C3	124.75 (12)	C13—C14—H14	119.6
N1—N2—C3	119.92 (11)	C16—C15—C14	118.96 (16)
C2—N3—C1	109.06 (11)	C16—C15—H15	120.5
C2—N3—N4	122.82 (11)	C14—C15—H15	120.5
C1—N3—N4	125.91 (11)	C15—C16—C17	120.56 (16)
C24—N4—N3	115.83 (12)	C15—C16—H16	119.7
N2—C1—N3	102.24 (11)	C17—C16—H16	119.7
N2—C1—S1	127.65 (11)	C12—C17—C16	121.15 (16)
N3—C1—S1	130.08 (11)	C12—C17—H17	119.4
N1—C2—N3	109.77 (12)	C16—C17—H17	119.4
N1—C2—C18	122.42 (12)	C19—C18—C23	119.04 (14)
N3—C2—C18	127.77 (12)	C19—C18—C2	123.69 (14)
N2—C3—C12	110.20 (11)	C23—C18—C2	117.27 (13)
N2—C3—C4	109.44 (11)	C20—C19—C18	120.17 (15)
C12—C3—C4	112.21 (12)	C20—C19—H19	119.9
N2—C3—H3	108.3	C18—C19—H19	119.9
C12—C3—H3	108.3	C21—C20—C19	120.59 (16)
C4—C3—H3	108.3	C21—C20—H20	119.7
C5—C4—C3	112.33 (13)	C19—C20—H20	119.7
C5—C4—H4A	109.1	C20—C21—C22	119.37 (15)
C3—C4—H4A	109.1	C20—C21—H21	120.3
C5—C4—H4B	109.1	C22—C21—H21	120.3
C3—C4—H4B	109.1	C23—C22—C21	120.75 (15)
H4A—C4—H4B	107.9	C23—C22—H22	119.6
O1—C5—C6	120.73 (15)	C21—C22—H22	119.6
O1—C5—C4	120.89 (14)	C22—C23—C18	120.07 (15)
C6—C5—C4	118.38 (15)	C22—C23—H23	120.0
C7—C6—C11	119.05 (16)	C18—C23—H23	120.0
C7—C6—C5	123.21 (15)	N4—C24—C25	120.16 (13)
C11—C6—C5	117.73 (17)	N4—C24—H24	119.9
C6—C7—C8	120.28 (18)	C25—C24—H24	119.9
C6—C7—H7	119.9	C30—C25—C26	118.44 (13)
C8—C7—H7	119.9	C30—C25—C24	118.69 (13)
C9—C8—C7	119.4 (2)	C26—C25—C24	122.78 (13)
C9—C8—H8	120.3	O2—C26—C27	118.16 (13)
C7—C8—H8	120.3	O2—C26—C25	121.82 (13)
C10—C9—C8	120.97 (19)	C27—C26—C25	120.02 (13)
C10—C9—H9	119.5	C28—C27—C26	120.05 (14)
C8—C9—H9	119.5	C28—C27—H27	120.0
C11—C10—C9	119.3 (2)	C26—C27—H27	120.0
C11—C10—H10	120.4	C27—C28—C29	121.10 (15)
C9—C10—H10	120.4	C27—C28—H28	119.4
C10—C11—C6	121.0 (2)	C29—C28—H28	119.4
C10—C11—H11	119.5	C30—C29—C28	118.73 (15)
C6—C11—H11	119.5	C30—C29—H29	120.6
C13—C12—C17	117.74 (14)	C28—C29—H29	120.6
C13—C12—C3	122.08 (13)	C29—C30—C25	121.65 (14)
C17—C12—C3	120.17 (14)	C29—C30—H30	119.2
C12—C13—C14	120.78 (15)	C25—C30—H30	119.2
C12—C13—H13	119.6
C2—N1—N2—C1	0.44 (15)	N2—C3—C12—C13	52.78 (19)
C2—N1—N2—C3	166.47 (11)	C4—C3—C12—C13	−69.45 (18)
C2—N3—N4—C24	−150.62 (12)	N2—C3—C12—C17	−126.17 (15)
C1—N3—N4—C24	48.15 (18)	C4—C3—C12—C17	111.60 (16)
N1—N2—C1—N3	−2.54 (15)	C17—C12—C13—C14	−1.0 (2)
C3—N2—C1—N3	−167.79 (12)	C3—C12—C13—C14	179.99 (15)
N1—N2—C1—S1	175.64 (10)	C12—C13—C14—C15	−1.1 (3)
C3—N2—C1—S1	10.4 (2)	C13—C14—C15—C16	2.6 (3)
C2—N3—C1—N2	3.62 (14)	C14—C15—C16—C17	−2.0 (3)
N4—N3—C1—N2	167.00 (12)	C13—C12—C17—C16	1.6 (3)
C2—N3—C1—S1	−174.50 (11)	C3—C12—C17—C16	−179.37 (16)
N4—N3—C1—S1	−11.1 (2)	C15—C16—C17—C12	−0.1 (3)
N2—N1—C2—N3	1.96 (15)	N1—C2—C18—C19	−160.38 (14)
N2—N1—C2—C18	−175.88 (12)	N3—C2—C18—C19	22.2 (2)
C1—N3—C2—N1	−3.66 (16)	N1—C2—C18—C23	19.7 (2)
N4—N3—C2—N1	−167.66 (12)	N3—C2—C18—C23	−157.76 (13)
C1—N3—C2—C18	174.03 (13)	C23—C18—C19—C20	0.7 (2)
N4—N3—C2—C18	10.0 (2)	C2—C18—C19—C20	−179.24 (13)
C1—N2—C3—C12	82.90 (17)	C18—C19—C20—C21	−0.7 (2)
N1—N2—C3—C12	−81.50 (15)	C19—C20—C21—C22	0.0 (2)
C1—N2—C3—C4	−153.26 (13)	C20—C21—C22—C23	0.7 (2)
N1—N2—C3—C4	42.35 (16)	C21—C22—C23—C18	−0.7 (2)
N2—C3—C4—C5	67.58 (16)	C19—C18—C23—C22	0.0 (2)
C12—C3—C4—C5	−169.76 (12)	C2—C18—C23—C22	179.93 (13)
C3—C4—C5—O1	15.4 (2)	N3—N4—C24—C25	−173.25 (12)
C3—C4—C5—C6	−164.39 (14)	N4—C24—C25—C30	177.34 (13)
O1—C5—C6—C7	178.74 (16)	N4—C24—C25—C26	0.9 (2)
C4—C5—C6—C7	−1.5 (2)	C30—C25—C26—O2	178.39 (13)
O1—C5—C6—C11	−1.7 (2)	C24—C25—C26—O2	−5.1 (2)
C4—C5—C6—C11	178.03 (14)	C30—C25—C26—C27	−0.7 (2)
C11—C6—C7—C8	−1.8 (3)	C24—C25—C26—C27	175.84 (13)
C5—C6—C7—C8	177.74 (16)	O2—C26—C27—C28	−178.70 (13)
C6—C7—C8—C9	0.7 (3)	C25—C26—C27—C28	0.4 (2)
C7—C8—C9—C10	1.2 (3)	C26—C27—C28—C29	0.4 (2)
C8—C9—C10—C11	−1.9 (3)	C27—C28—C29—C30	−0.9 (2)
C9—C10—C11—C6	0.7 (3)	C28—C29—C30—C25	0.6 (2)
C7—C6—C11—C10	1.1 (3)	C26—C25—C30—C29	0.2 (2)
C5—C6—C11—C10	−178.46 (17)	C24—C25—C30—C29	−176.46 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N4	1.00 (3)	1.73 (2)	2.6226 (19)	147.4 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N4	1.00 (3)	1.73 (2)	2.6226 (19)	147.4 (19)