N-[(3-Methyl-5-phen-oxy-1-phenyl-pyrazol-4-yl)carbon-yl]-N'-(5-propyl-1,3,4-thia-diazol-2-yl)thio-urea.

In the crystal structure of the title compound, C(23)H(22)N(6)O(2)S(2), there are two intra-molecular N-H⋯O hydrogen bonds. The propyl chain is disordered over two sites, with occupancy factors of 0.639 (5) and 0.361 (5).

Related literature

For pharmacological and biological properties, see: Ranise et al. (2003 ▶); Akbas et al. (2005 ▶); Daidone et al. (2004 ▶); Park et al. (2005 ▶); Thomasco et al. (2003 ▶); Foroumadi et al. (2002 ▶); Supuran & Scozzafava (2000 ▶).

Experimental

Crystal data

C23H22N6O2S2

M = 478.58

Triclinic,

a = 8.4489 (3) Å

b = 9.9099 (4) Å

c = 14.3492 (5) Å

α = 86.089 (1)°

β = 74.048 (1)°

γ = 81.591 (1)°

V = 1142.25 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.27 mm−1

T = 153 (2) K

0.32 × 0.15 × 0.13 mm

Data collection

Rigaku R-AXIS SPIDER diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.919, T max = 0.966

11326 measured reflections

5171 independent reflections

3376 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.165

S = 1.05

5171 reflections

317 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.54 e Å−3

Data collection: RAPID-AUTO (Rigaku 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807068353/rk2066sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068353/rk2066Isup2.hkl

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

C23H22N6O2S2	Z = 2
Mr = 478.58	F000 = 500
Triclinic, P1	Dx = 1.391 Mg m−3
Hall symbol: -P 1	Melting point = 461–463 K
a = 8.4489 (3) Å	Mo Kα radiation λ = 0.71073 Å
b = 9.9099 (4) Å	Cell parameters from 7971 reflections
c = 14.3492 (5) Å	θ = 3.1–27.5º
α = 86.089 (1)º	µ = 0.27 mm−1
β = 74.048 (1)º	T = 153 (2) K
γ = 81.591 (1)º	Block, yellow
V = 1142.25 (7) Å3	0.32 × 0.15 × 0.13 mm

Rigaku R-AXIS Spider diffractometer	5171 independent reflections
Radiation source: fine-focus sealed tube	3376 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.024
T = 153(2) K	θmax = 27.5º
ω scans	θmin = 3.1º
Absorption correction: empirical (using intensity measurements)(ABSCOR; Higashi, 1995)	h = −10→10
Tmin = 0.919, Tmax = 0.966	k = −12→12
11326 measured reflections	l = −18→18

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)] = 0.042	H-atom parameters constrained
wR(F2) = 0.165	w = 1/[σ2(Fo2) + (0.1061P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
5171 reflections	Δρmax = 0.36 e Å−3
317 parameters	Δρmin = −0.54 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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 > 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	Occ. (<1)
S1	0.56160 (7)	0.15893 (6)	0.37164 (4)	0.04016 (19)
S2	0.56697 (9)	0.18955 (7)	0.58112 (5)	0.0511 (2)
O1	0.72651 (18)	0.43251 (15)	0.78717 (10)	0.0330 (3)
O2	0.7995 (2)	0.57769 (18)	0.48360 (11)	0.0438 (4)
N1	0.8356 (2)	0.63699 (19)	0.78887 (13)	0.0328 (4)
N2	0.8911 (2)	0.74382 (19)	0.72761 (13)	0.0360 (4)
N3	0.6887 (2)	0.4151 (2)	0.59251 (13)	0.0346 (4)
H3A	0.6652	0.3916	0.6546	0.042*
N4	0.6649 (2)	0.3756 (2)	0.44130 (13)	0.0357 (4)
H4A	0.7085	0.4522	0.4261	0.043*
N5	0.6442 (3)	0.3835 (2)	0.28420 (14)	0.0439 (5)
N6	0.6035 (3)	0.3101 (2)	0.21699 (14)	0.0480 (5)
C1	0.9603 (3)	0.6775 (3)	0.91597 (18)	0.0408 (5)
H1A	1.0540	0.7037	0.8681	0.049*
C2	0.9530 (3)	0.6782 (3)	1.01344 (19)	0.0467 (6)
H2B	1.0420	0.7061	1.0326	0.056*
C3	0.8177 (3)	0.6388 (3)	1.08327 (18)	0.0452 (6)
H3B	0.8146	0.6389	1.1500	0.054*
C4	0.6870 (3)	0.5994 (3)	1.05608 (17)	0.0418 (6)
H4B	0.5946	0.5714	1.1041	0.050*
C5	0.6905 (3)	0.6005 (2)	0.95854 (16)	0.0364 (5)
H5B	0.5996	0.5761	0.9395	0.044*
C6	0.8294 (3)	0.6380 (2)	0.88941 (16)	0.0336 (5)
C7	0.9194 (3)	0.8149 (3)	0.55833 (18)	0.0433 (6)
H7A	0.9635	0.8908	0.5786	0.065*
H7B	0.8206	0.8502	0.5366	0.065*
H7C	1.0040	0.7683	0.5050	0.065*
C8	0.8741 (3)	0.7167 (2)	0.64179 (16)	0.0354 (5)
C9	0.8061 (3)	0.5921 (2)	0.64604 (15)	0.0325 (5)
C10	0.7862 (3)	0.5469 (2)	0.74127 (16)	0.0320 (5)
C11	0.8364 (3)	0.3093 (2)	0.77255 (14)	0.0283 (4)
C12	0.7675 (3)	0.1955 (3)	0.81626 (19)	0.0417 (6)
H12A	0.6567	0.2036	0.8563	0.050*
C13	0.8630 (3)	0.0697 (3)	0.8006 (2)	0.0516 (7)
H13A	0.8178	−0.0100	0.8302	0.062*
C14	1.0242 (3)	0.0589 (3)	0.7422 (2)	0.0530 (7)
H14A	1.0888	−0.0282	0.7308	0.064*
C15	1.0906 (3)	0.1736 (3)	0.70074 (19)	0.0473 (6)
H15A	1.2016	0.1657	0.6609	0.057*
C16	0.9973 (3)	0.3014 (3)	0.71634 (16)	0.0370 (5)
H16A	1.0438	0.3814	0.6887	0.044*
C17	0.7669 (3)	0.5307 (2)	0.56726 (16)	0.0329 (5)
C18	0.6421 (3)	0.3310 (2)	0.53439 (16)	0.0335 (5)
C19	0.6281 (3)	0.3158 (2)	0.36680 (16)	0.0351 (5)
C20	0.5602 (3)	0.1932 (3)	0.25151 (17)	0.0428 (6)
C21	0.5096 (4)	0.0933 (3)	0.1944 (2)	0.0555 (7)
H21A	0.4153	0.0522	0.2383	0.067*
H21B	0.4675	0.1455	0.1428	0.067*
C22	0.6339 (5)	−0.0172 (4)	0.1491 (3)	0.0465 (11)	0.639 (5)
H22A	0.5827	−0.0767	0.1163	0.056*	0.639 (5)
H22B	0.6754	−0.0730	0.1995	0.056*	0.639 (5)
C23	0.7787 (7)	0.0383 (5)	0.0753 (3)	0.0568 (13)	0.639 (5)
H23A	0.8616	−0.0378	0.0465	0.085*	0.639 (5)
H23B	0.8293	0.0972	0.1077	0.085*	0.639 (5)
H23C	0.7381	0.0912	0.0243	0.085*	0.639 (5)
C22'	0.6510 (12)	0.0828 (9)	0.0931 (5)	0.053 (2)	0.361 (5)
H22C	0.6563	0.1730	0.0591	0.064*	0.361 (5)
H22D	0.7611	0.0490	0.1038	0.064*	0.361 (5)
C23'	0.6019 (12)	−0.0149 (10)	0.0362 (6)	0.064 (3)	0.361 (5)
H23D	0.6845	−0.0268	−0.0267	0.096*	0.361 (5)
H23E	0.4931	0.0205	0.0260	0.096*	0.361 (5)
H23F	0.5954	−0.1029	0.0715	0.096*	0.361 (5)

	U11	U22	U33	U12	U13	U23
S1	0.0411 (3)	0.0325 (3)	0.0431 (3)	−0.0066 (2)	−0.0042 (3)	−0.0007 (2)
S2	0.0611 (4)	0.0503 (4)	0.0486 (4)	−0.0317 (3)	−0.0178 (3)	0.0171 (3)
O1	0.0335 (8)	0.0240 (8)	0.0338 (8)	−0.0074 (6)	0.0049 (6)	0.0028 (6)
O2	0.0581 (11)	0.0374 (10)	0.0327 (8)	−0.0179 (8)	−0.0026 (8)	0.0059 (7)
N1	0.0345 (9)	0.0273 (10)	0.0335 (9)	−0.0100 (8)	−0.0016 (8)	0.0017 (8)
N2	0.0399 (10)	0.0260 (10)	0.0380 (10)	−0.0109 (8)	−0.0015 (8)	0.0055 (8)
N3	0.0350 (10)	0.0361 (11)	0.0306 (9)	−0.0125 (8)	−0.0027 (8)	0.0046 (8)
N4	0.0368 (10)	0.0328 (11)	0.0341 (9)	−0.0113 (8)	−0.0009 (8)	0.0025 (8)
N5	0.0511 (12)	0.0401 (12)	0.0344 (10)	−0.0093 (10)	0.0008 (9)	−0.0035 (9)
N6	0.0606 (14)	0.0455 (14)	0.0335 (10)	−0.0092 (11)	−0.0020 (10)	−0.0095 (9)
C1	0.0337 (12)	0.0384 (14)	0.0479 (13)	−0.0099 (10)	−0.0050 (11)	0.0007 (11)
C2	0.0472 (14)	0.0464 (16)	0.0520 (15)	−0.0117 (12)	−0.0202 (12)	−0.0003 (12)
C3	0.0545 (15)	0.0401 (15)	0.0429 (13)	−0.0073 (12)	−0.0157 (12)	−0.0015 (11)
C4	0.0441 (13)	0.0412 (14)	0.0363 (12)	−0.0096 (11)	−0.0024 (11)	−0.0015 (10)
C5	0.0322 (11)	0.0381 (13)	0.0357 (11)	−0.0091 (10)	−0.0016 (9)	−0.0014 (10)
C6	0.0359 (11)	0.0248 (11)	0.0356 (11)	−0.0041 (9)	−0.0029 (9)	0.0021 (9)
C7	0.0466 (13)	0.0353 (14)	0.0425 (13)	−0.0110 (11)	−0.0026 (11)	0.0099 (10)
C8	0.0352 (11)	0.0273 (12)	0.0376 (11)	−0.0055 (9)	0.0004 (10)	0.0014 (9)
C9	0.0313 (11)	0.0259 (11)	0.0332 (11)	−0.0043 (9)	0.0029 (9)	0.0013 (9)
C10	0.0296 (10)	0.0242 (11)	0.0367 (11)	−0.0054 (8)	0.0007 (9)	0.0005 (9)
C11	0.0316 (10)	0.0262 (11)	0.0272 (9)	−0.0060 (8)	−0.0065 (8)	−0.0029 (8)
C12	0.0357 (12)	0.0302 (13)	0.0578 (15)	−0.0106 (10)	−0.0077 (11)	0.0013 (11)
C13	0.0462 (14)	0.0266 (13)	0.084 (2)	−0.0097 (11)	−0.0190 (14)	0.0010 (13)
C14	0.0469 (15)	0.0330 (14)	0.080 (2)	0.0041 (12)	−0.0211 (14)	−0.0101 (13)
C15	0.0344 (12)	0.0494 (16)	0.0518 (14)	0.0023 (11)	−0.0049 (11)	−0.0035 (12)
C16	0.0361 (12)	0.0368 (13)	0.0359 (11)	−0.0075 (10)	−0.0057 (10)	0.0041 (10)
C17	0.0287 (10)	0.0288 (11)	0.0342 (11)	−0.0025 (9)	0.0028 (9)	−0.0005 (9)
C18	0.0266 (10)	0.0362 (13)	0.0346 (11)	−0.0069 (9)	−0.0024 (9)	0.0031 (9)
C19	0.0318 (11)	0.0286 (12)	0.0372 (11)	−0.0041 (9)	0.0035 (9)	−0.0013 (9)
C20	0.0478 (14)	0.0350 (14)	0.0384 (12)	−0.0033 (11)	0.0005 (11)	−0.0074 (10)
C21	0.0705 (19)	0.0468 (17)	0.0462 (15)	−0.0094 (14)	−0.0078 (14)	−0.0112 (13)
C22	0.051 (2)	0.038 (2)	0.054 (2)	−0.0081 (18)	−0.019 (2)	−0.0067 (19)
C23	0.063 (3)	0.052 (3)	0.046 (2)	−0.013 (2)	0.006 (2)	−0.015 (2)
C22'	0.064 (6)	0.050 (5)	0.042 (4)	−0.015 (4)	−0.004 (4)	−0.013 (4)
C23'	0.093 (6)	0.064 (6)	0.042 (4)	−0.034 (5)	−0.017 (4)	−0.006 (4)

S1—C19	1.719 (2)	C7—H7C	0.9800
S1—C20	1.737 (2)	C8—C9	1.427 (3)
S2—C18	1.648 (2)	C9—C10	1.381 (3)
O1—C10	1.362 (3)	C9—C17	1.455 (3)
O1—C11	1.411 (3)	C11—C16	1.371 (3)
O2—C17	1.230 (3)	C11—C12	1.378 (3)
N1—C10	1.337 (3)	C12—C13	1.378 (4)
N1—N2	1.380 (2)	C12—H12A	0.9500
N1—C6	1.430 (3)	C13—C14	1.382 (4)
N2—C8	1.328 (3)	C13—H13A	0.9500
N3—C17	1.383 (3)	C14—C15	1.368 (4)
N3—C18	1.384 (3)	C14—H14A	0.9500
N3—H3A	0.8800	C15—C16	1.387 (3)
N4—C18	1.349 (3)	C15—H15A	0.9500
N4—C19	1.384 (3)	C16—H16A	0.9500
N4—H4A	0.8800	C20—C21	1.503 (4)
N5—C19	1.305 (3)	C21—C22	1.453 (5)
N5—N6	1.389 (3)	C21—C22'	1.607 (8)
N6—C20	1.292 (3)	C21—H21A	0.9900
C1—C6	1.379 (3)	C21—H21B	0.9900
C1—C2	1.383 (3)	C22—C23	1.525 (6)
C1—H1A	0.9500	C22—H22A	0.9900
C2—C3	1.382 (4)	C22—H22B	0.9900
C2—H2B	0.9500	C23—H23A	0.9800
C3—C4	1.381 (3)	C23—H23B	0.9800
C3—H3B	0.9500	C23—H23C	0.9800
C4—C5	1.391 (3)	C22'—C23'	1.479 (10)
C4—H4B	0.9500	C22'—H22C	0.9900
C5—C6	1.392 (3)	C22'—H22D	0.9900
C5—H5B	0.9500	C23'—H23D	0.9800
C7—C8	1.492 (3)	C23'—H23E	0.9800
C7—H7A	0.9800	C23'—H23F	0.9800
C7—H7B	0.9800
C19—S1—C20	85.87 (11)	C15—C14—C13	120.0 (2)
C10—O1—C11	116.95 (16)	C15—C14—H14A	120.0
C10—N1—N2	110.63 (17)	C13—C14—H14A	120.0
C10—N1—C6	129.28 (19)	C14—C15—C16	120.6 (2)
N2—N1—C6	120.00 (17)	C14—C15—H15A	119.7
C8—N2—N1	105.57 (18)	C16—C15—H15A	119.7
C17—N3—C18	129.42 (18)	C11—C16—C15	118.4 (2)
C17—N3—H3A	115.3	C11—C16—H16A	120.8
C18—N3—H3A	115.3	C15—C16—H16A	120.8
C18—N4—C19	128.0 (2)	O2—C17—N3	121.6 (2)
C18—N4—H4A	116.0	O2—C17—C9	122.9 (2)
C19—N4—H4A	116.0	N3—C17—C9	115.49 (19)
C19—N5—N6	111.0 (2)	N4—C18—N3	114.41 (19)
C20—N6—N5	112.6 (2)	N4—C18—S2	125.85 (18)
C6—C1—C2	118.9 (2)	N3—C18—S2	119.73 (16)
C6—C1—H1A	120.5	N5—C19—N4	117.9 (2)
C2—C1—H1A	120.5	N5—C19—S1	115.74 (18)
C3—C2—C1	120.8 (2)	N4—C19—S1	126.40 (17)
C3—C2—H2B	119.6	N6—C20—C21	123.7 (2)
C1—C2—H2B	119.6	N6—C20—S1	114.75 (18)
C4—C3—C2	120.0 (2)	C21—C20—S1	121.5 (2)
C4—C3—H3B	120.0	C22—C21—C20	118.1 (3)
C2—C3—H3B	120.0	C22—C21—C22'	47.1 (4)
C3—C4—C5	120.1 (2)	C20—C21—C22'	104.9 (3)
C3—C4—H4B	119.9	C22—C21—H21A	107.8
C5—C4—H4B	119.9	C20—C21—H21A	107.8
C4—C5—C6	118.9 (2)	C22'—C21—H21A	146.2
C4—C5—H5B	120.6	C22—C21—H21B	107.8
C6—C5—H5B	120.6	C20—C21—H21B	107.8
C1—C6—C5	121.3 (2)	C22'—C21—H21B	69.9
C1—C6—N1	119.4 (2)	H21A—C21—H21B	107.1
C5—C6—N1	119.32 (19)	C21—C22—C23	110.9 (4)
C8—C7—H7A	109.5	C21—C22—H22A	109.5
C8—C7—H7B	109.5	C23—C22—H22A	109.5
H7A—C7—H7B	109.5	C21—C22—H22B	109.5
C8—C7—H7C	109.5	C23—C22—H22B	109.5
H7A—C7—H7C	109.5	H22A—C22—H22B	108.0
H7B—C7—H7C	109.5	C22—C23—H23A	109.5
N2—C8—C9	111.13 (19)	C22—C23—H23B	109.5
N2—C8—C7	119.6 (2)	H23A—C23—H23B	109.5
C9—C8—C7	129.2 (2)	C22—C23—H23C	109.5
C10—C9—C8	103.68 (19)	H23A—C23—H23C	109.5
C10—C9—C17	129.3 (2)	H23B—C23—H23C	109.5
C8—C9—C17	127.0 (2)	C23'—C22'—C21	105.3 (6)
N1—C10—O1	121.07 (19)	C23'—C22'—H22C	110.7
N1—C10—C9	108.98 (19)	C21—C22'—H22C	110.7
O1—C10—C9	130.0 (2)	C23'—C22'—H22D	110.7
C16—C11—C12	122.1 (2)	C21—C22'—H22D	110.7
C16—C11—O1	123.2 (2)	H22C—C22'—H22D	108.8
C12—C11—O1	114.70 (18)	C22'—C23'—H23D	109.5
C11—C12—C13	118.6 (2)	C22'—C23'—H23E	109.5
C11—C12—H12A	120.7	H23D—C23'—H23E	109.5
C13—C12—H12A	120.7	C22'—C23'—H23F	109.5
C12—C13—C14	120.3 (2)	H23D—C23'—H23F	109.5
C12—C13—H13A	119.8	H23E—C23'—H23F	109.5
C14—C13—H13A	119.8
C10—N1—N2—C8	0.1 (2)	C11—C12—C13—C14	−0.1 (4)
C6—N1—N2—C8	−176.87 (19)	C12—C13—C14—C15	1.1 (4)
C19—N5—N6—C20	−0.2 (3)	C13—C14—C15—C16	−0.4 (4)
C6—C1—C2—C3	0.6 (4)	C12—C11—C16—C15	2.3 (3)
C1—C2—C3—C4	−0.6 (4)	O1—C11—C16—C15	−175.1 (2)
C2—C3—C4—C5	−0.6 (4)	C14—C15—C16—C11	−1.3 (4)
C3—C4—C5—C6	1.9 (4)	C18—N3—C17—O2	3.3 (4)
C2—C1—C6—C5	0.6 (4)	C18—N3—C17—C9	−177.0 (2)
C2—C1—C6—N1	179.9 (2)	C10—C9—C17—O2	−175.8 (2)
C4—C5—C6—C1	−1.9 (4)	C8—C9—C17—O2	5.0 (4)
C4—C5—C6—N1	178.8 (2)	C10—C9—C17—N3	4.6 (3)
C10—N1—C6—C1	140.6 (2)	C8—C9—C17—N3	−174.7 (2)
N2—N1—C6—C1	−43.1 (3)	C19—N4—C18—N3	−178.9 (2)
C10—N1—C6—C5	−40.1 (3)	C19—N4—C18—S2	1.5 (3)
N2—N1—C6—C5	136.3 (2)	C17—N3—C18—N4	−5.9 (3)
N1—N2—C8—C9	0.4 (2)	C17—N3—C18—S2	173.78 (18)
N1—N2—C8—C7	178.47 (19)	N6—N5—C19—N4	179.78 (19)
N2—C8—C9—C10	−0.7 (2)	N6—N5—C19—S1	−0.4 (3)
C7—C8—C9—C10	−178.6 (2)	C18—N4—C19—N5	173.0 (2)
N2—C8—C9—C17	178.7 (2)	C18—N4—C19—S1	−6.8 (3)
C7—C8—C9—C17	0.9 (4)	C20—S1—C19—N5	0.63 (19)
N2—N1—C10—O1	179.90 (18)	C20—S1—C19—N4	−179.6 (2)
C6—N1—C10—O1	−3.5 (3)	N5—N6—C20—C21	179.9 (2)
N2—N1—C10—C9	−0.6 (2)	N5—N6—C20—S1	0.7 (3)
C6—N1—C10—C9	176.1 (2)	C19—S1—C20—N6	−0.7 (2)
C11—O1—C10—N1	−101.1 (2)	C19—S1—C20—C21	−179.9 (2)
C11—O1—C10—C9	79.5 (3)	N6—C20—C21—C22	97.3 (4)
C8—C9—C10—N1	0.7 (2)	S1—C20—C21—C22	−83.6 (3)
C17—C9—C10—N1	−178.7 (2)	N6—C20—C21—C22'	48.3 (5)
C8—C9—C10—O1	−179.8 (2)	S1—C20—C21—C22'	−132.6 (4)
C17—C9—C10—O1	0.8 (4)	C20—C21—C22—C23	−61.3 (4)
C10—O1—C11—C16	0.9 (3)	C22'—C21—C22—C23	23.1 (5)
C10—O1—C11—C12	−176.69 (18)	C22—C21—C22'—C23'	65.6 (6)
C16—C11—C12—C13	−1.7 (4)	C20—C21—C22'—C23'	−179.7 (6)
O1—C11—C12—C13	175.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.88	2.18	2.917 (2)	141
N4—H4A···O2	0.88	1.89	2.623 (2)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1	0.88	2.18	2.917 (2)	141
N4—H4A⋯O2	0.88	1.89	2.623 (2)	139