1,5-Dimethyl-4-{[(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl-idene)(thio-phen-2-yl)meth-yl]amino}-2-phenyl-1H-pyrazol-3(2H)-one.

In the title compound, C(26)H(23)N(5)O(2)S, an intra-molecular N-H⋯O inter-action generates an S(6) ring. The essentially planar S(6) and pyrazole rings [maximum deviations = -0.0270 (14) and 0.0195 (15) Å, respectively] are nearly coplanar, making a dihedral angle of 3.94 (6)°. The S(6) ring makes dihedral angles of 23.79 (6), 78.53 (6) and 67.91 (6)° with the pyrazolone ring, the pyrazole ring and the benzene ring of anti-pyrine, respectively. The structure exhibits a thienyl-ring flip disorder with occupancy factors in the ratio 0.82:0.18.

Related literature

For general background to pyrazolo­nes, see: Casas et al. (2007 ▶). For the anti­bacterial activity of pyrazolone Schiff bases, see: Zhang et al. (2008 ▶); Li et al. (2000 ▶). For our previous work in this area, see: Zhu et al. (2010a ▶,b ▶). For related structures, see: Shi et al. (2005 ▶); Goh et al. (2009 ▶). For disordered thienyl rings, see: Crundwell et al. (2003 ▶).

Experimental

Crystal data

C26H23N5O2S

M = 469.55

Monoclinic,

a = 27.098 (3) Å

b = 7.9045 (8) Å

c = 22.308 (2) Å

β = 99.011 (8)°

V = 4719.4 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.17 mm−1

T = 293 K

0.42 × 0.36 × 0.34 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ▶) T min = 0.932, T max = 0.944

22080 measured reflections

5570 independent reflections

3806 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.144

S = 1.02

5570 reflections

322 parameters

22 restraints

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); 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: ORTEPIII (Burnett & Johnson, 1996 ▶) and ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811002467/dn2653sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811002467/dn2653Isup2.hkl

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

C26H23N5O2S	F(000) = 1968
Mr = 469.55	Dx = 1.322 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -C 2yc	Cell parameters from 5913 reflections
a = 27.098 (3) Å	θ = 2.6–27.9°
b = 7.9045 (8) Å	µ = 0.17 mm−1
c = 22.308 (2) Å	T = 293 K
β = 99.011 (8)°	Prism, colourless
V = 4719.4 (9) Å3	0.42 × 0.36 × 0.34 mm
Z = 8

Rigaku Saturn diffractometer	5570 independent reflections
Radiation source: rotating anode	3806 reflections with I > 2σ(I)
multilayer	Rint = 0.037
Detector resolution: 7.31 pixels mm-1	θmax = 27.9°, θmin = 2.6°
ω scans	h = −35→35
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	k = −10→8
Tmin = 0.932, Tmax = 0.944	l = −29→29
22080 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0825P)2] where P = (Fo2 + 2Fc2)/3
5570 reflections	(Δ/σ)max = 0.003
322 parameters	Δρmax = 0.23 e Å−3
22 restraints	Δρmin = −0.25 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 > 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	Occ. (<1)
O1	0.25433 (4)	1.02510 (13)	0.08661 (6)	0.0607 (3)
O2	0.08792 (4)	0.72515 (16)	−0.01432 (5)	0.0574 (3)
N1	0.30507 (4)	0.78662 (15)	0.09168 (6)	0.0454 (3)
N2	0.29718 (5)	0.61104 (15)	0.09307 (6)	0.0453 (3)
N3	0.17055 (5)	0.75910 (17)	0.06681 (6)	0.0490 (3)
H3	0.1558	0.7573	0.0298	0.059*
N4	0.01707 (5)	0.77052 (16)	0.03130 (6)	0.0483 (3)
N5	0.00673 (5)	0.81903 (18)	0.08851 (7)	0.0531 (4)
C1	0.25902 (6)	0.87031 (19)	0.08467 (7)	0.0440 (4)
C2	0.22290 (5)	0.73667 (18)	0.07704 (7)	0.0418 (3)
C3	0.24689 (6)	0.58580 (18)	0.07935 (7)	0.0431 (3)
C4	0.22546 (7)	0.4148 (2)	0.06696 (9)	0.0652 (5)
H4A	0.1900	0.4190	0.0665	0.098*
H4B	0.2402	0.3383	0.0981	0.098*
H4C	0.2323	0.3762	0.0283	0.098*
C5	0.35010 (6)	0.8549 (2)	0.12487 (7)	0.0473 (4)
C6	0.36892 (6)	1.0029 (2)	0.10435 (8)	0.0560 (4)
H6	0.3523	1.0563	0.0698	0.067*
C7	0.41249 (7)	1.0712 (3)	0.13541 (11)	0.0717 (6)
H7	0.4250	1.1720	0.1223	0.086*
C8	0.43721 (8)	0.9902 (3)	0.18544 (12)	0.0836 (7)
H8	0.4667	1.0357	0.2060	0.100*
C9	0.41887 (8)	0.8425 (3)	0.20554 (10)	0.0843 (6)
H9	0.4363	0.7876	0.2392	0.101*
C10	0.37464 (7)	0.7747 (3)	0.17596 (9)	0.0655 (5)
H10	0.3616	0.6765	0.1903	0.079*
C11	0.33387 (7)	0.4992 (2)	0.07232 (9)	0.0628 (5)
H11A	0.3337	0.3918	0.0924	0.094*
H11B	0.3665	0.5489	0.0816	0.094*
H11C	0.3256	0.4832	0.0293	0.094*
C12	0.14164 (6)	0.78314 (18)	0.11001 (7)	0.0431 (4)
S1	0.16071 (3)	0.63681 (8)	0.22363 (3)	0.0702 (2)	0.82
C13	0.16636 (6)	0.79831 (19)	0.17339 (7)	0.0468 (4)	0.82
C14	0.19533 (11)	0.9188 (3)	0.20297 (12)	0.0704 (8)	0.82
H14	0.2031	1.0169	0.1834	0.085*	0.82
C15	0.21288 (18)	0.8917 (6)	0.26270 (14)	0.0765 (8)	0.82
H15	0.2330	0.9675	0.2874	0.092*	0.82
C16	0.19767 (14)	0.7430 (5)	0.28143 (13)	0.0709 (9)	0.82
H16	0.2060	0.7018	0.3208	0.085*	0.82
S1'	0.20046 (19)	0.9710 (5)	0.1965 (2)	0.0702 (2)	0.18
C13'	0.16636 (6)	0.79831 (19)	0.17339 (7)	0.0468 (4)	0.18
C14'	0.1637 (5)	0.6894 (16)	0.2181 (5)	0.0704 (8)	0.18
H14'	0.1463	0.5877	0.2123	0.085*	0.18
C15'	0.1879 (8)	0.738 (2)	0.2721 (6)	0.0765 (8)	0.18
H15'	0.1895	0.6745	0.3075	0.092*	0.18
C16'	0.2097 (7)	0.889 (2)	0.2692 (6)	0.0709 (9)	0.18
H16'	0.2278	0.9432	0.3025	0.085*	0.18
C17	0.06744 (5)	0.75638 (19)	0.03103 (7)	0.0449 (4)
C18	0.09039 (6)	0.78841 (18)	0.09237 (7)	0.0437 (4)
C19	0.04936 (6)	0.8289 (2)	0.12425 (8)	0.0504 (4)
C20	0.05032 (7)	0.8851 (3)	0.18855 (9)	0.0727 (6)
H20A	0.0181	0.9285	0.1934	0.109*
H20B	0.0750	0.9721	0.1982	0.109*
H20C	0.0585	0.7907	0.2153	0.109*
C21	−0.02273 (6)	0.75001 (19)	−0.01723 (7)	0.0468 (4)
C22	−0.01595 (7)	0.6573 (2)	−0.06807 (8)	0.0579 (4)
H22	0.0149	0.6082	−0.0706	0.069*
C23	−0.05544 (7)	0.6384 (2)	−0.11491 (9)	0.0648 (5)
H23	−0.0511	0.5759	−0.1490	0.078*
C24	−0.10124 (7)	0.7112 (2)	−0.11174 (9)	0.0650 (5)
H24	−0.1276	0.6986	−0.1436	0.078*
C25	−0.10744 (7)	0.8021 (2)	−0.06118 (9)	0.0618 (5)
H25	−0.1383	0.8510	−0.0588	0.074*
C26	−0.06879 (6)	0.8225 (2)	−0.01381 (9)	0.0540 (4)
H26	−0.0735	0.8844	0.0203	0.065*

	U11	U22	U33	U12	U13	U23
O1	0.0648 (7)	0.0375 (6)	0.0805 (9)	0.0072 (5)	0.0132 (6)	0.0016 (5)
O2	0.0493 (6)	0.0790 (8)	0.0465 (7)	0.0004 (6)	0.0160 (5)	−0.0109 (6)
N1	0.0438 (7)	0.0364 (7)	0.0564 (8)	0.0001 (5)	0.0095 (6)	−0.0004 (5)
N2	0.0477 (8)	0.0353 (7)	0.0541 (8)	0.0042 (5)	0.0122 (6)	−0.0015 (5)
N3	0.0451 (7)	0.0643 (8)	0.0390 (7)	0.0024 (6)	0.0108 (6)	−0.0003 (6)
N4	0.0422 (7)	0.0559 (8)	0.0494 (8)	−0.0021 (6)	0.0152 (6)	−0.0073 (6)
N5	0.0494 (8)	0.0609 (9)	0.0531 (8)	−0.0029 (6)	0.0206 (7)	−0.0073 (6)
C1	0.0466 (9)	0.0403 (8)	0.0462 (9)	0.0041 (7)	0.0108 (7)	0.0004 (6)
C2	0.0427 (8)	0.0444 (8)	0.0395 (8)	0.0028 (6)	0.0100 (6)	0.0004 (6)
C3	0.0506 (9)	0.0411 (8)	0.0393 (8)	−0.0014 (7)	0.0122 (7)	0.0008 (6)
C4	0.0727 (12)	0.0466 (10)	0.0756 (13)	−0.0091 (9)	0.0088 (10)	−0.0026 (8)
C5	0.0449 (9)	0.0492 (9)	0.0496 (9)	−0.0004 (7)	0.0132 (7)	−0.0053 (7)
C6	0.0548 (10)	0.0545 (10)	0.0615 (11)	−0.0064 (8)	0.0180 (8)	−0.0054 (8)
C7	0.0580 (12)	0.0731 (13)	0.0879 (15)	−0.0165 (10)	0.0234 (11)	−0.0217 (11)
C8	0.0542 (12)	0.1040 (18)	0.0905 (17)	−0.0113 (12)	0.0047 (12)	−0.0319 (14)
C9	0.0697 (14)	0.1072 (18)	0.0688 (14)	0.0025 (13)	−0.0116 (11)	−0.0062 (13)
C10	0.0655 (12)	0.0736 (13)	0.0562 (11)	−0.0005 (10)	0.0059 (9)	0.0044 (9)
C11	0.0650 (11)	0.0491 (10)	0.0797 (13)	0.0140 (8)	0.0277 (10)	−0.0015 (9)
C12	0.0502 (9)	0.0384 (8)	0.0426 (8)	−0.0014 (6)	0.0134 (7)	0.0004 (6)
S1	0.0933 (5)	0.0628 (5)	0.0532 (4)	−0.0107 (4)	0.0077 (3)	0.0143 (3)
C13	0.0493 (9)	0.0510 (9)	0.0418 (8)	0.0006 (7)	0.0129 (7)	−0.0007 (7)
C14	0.111 (2)	0.0564 (18)	0.0461 (14)	−0.0152 (16)	0.0183 (13)	0.0058 (12)
C15	0.0871 (19)	0.096 (2)	0.0469 (15)	−0.0203 (15)	0.0134 (14)	−0.0138 (14)
C16	0.079 (2)	0.093 (2)	0.0389 (14)	0.0077 (16)	0.0025 (13)	0.0086 (14)
S1'	0.0933 (5)	0.0628 (5)	0.0532 (4)	−0.0107 (4)	0.0077 (3)	0.0143 (3)
C13'	0.0493 (9)	0.0510 (9)	0.0418 (8)	0.0006 (7)	0.0129 (7)	−0.0007 (7)
C14'	0.111 (2)	0.0564 (18)	0.0461 (14)	−0.0152 (16)	0.0183 (13)	0.0058 (12)
C15'	0.0871 (19)	0.096 (2)	0.0469 (15)	−0.0203 (15)	0.0134 (14)	−0.0138 (14)
C16'	0.079 (2)	0.093 (2)	0.0389 (14)	0.0077 (16)	0.0025 (13)	0.0086 (14)
C17	0.0441 (9)	0.0447 (8)	0.0481 (9)	−0.0024 (7)	0.0144 (7)	−0.0034 (6)
C18	0.0440 (9)	0.0450 (8)	0.0447 (8)	−0.0030 (6)	0.0149 (7)	−0.0023 (6)
C19	0.0507 (10)	0.0533 (9)	0.0509 (9)	−0.0034 (7)	0.0197 (8)	−0.0041 (7)
C20	0.0693 (12)	0.0975 (16)	0.0566 (11)	0.0001 (10)	0.0262 (9)	−0.0158 (10)
C21	0.0442 (9)	0.0437 (8)	0.0537 (9)	−0.0050 (7)	0.0113 (7)	0.0004 (7)
C22	0.0509 (10)	0.0610 (11)	0.0621 (11)	0.0011 (8)	0.0097 (8)	−0.0105 (8)
C23	0.0668 (12)	0.0650 (12)	0.0613 (12)	−0.0039 (9)	0.0056 (9)	−0.0120 (9)
C24	0.0592 (11)	0.0631 (12)	0.0688 (12)	−0.0045 (9)	−0.0019 (9)	0.0008 (9)
C25	0.0492 (10)	0.0544 (11)	0.0810 (14)	0.0022 (8)	0.0077 (9)	0.0043 (9)
C26	0.0488 (10)	0.0487 (9)	0.0660 (11)	−0.0009 (7)	0.0138 (8)	−0.0033 (8)

O1—C1	1.2316 (17)	C12—C18	1.384 (2)
O2—C17	1.2524 (16)	C12—C13	1.472 (2)
N1—C1	1.3994 (19)	S1—C13	1.7213 (16)
N1—N2	1.4054 (17)	S1—C16	1.722 (3)
N1—C5	1.430 (2)	C13—C14	1.340 (3)
N2—C3	1.3637 (19)	C14—C15	1.360 (4)
N2—C11	1.4590 (19)	C14—H14	0.9300
N3—C12	1.3471 (18)	C15—C16	1.335 (3)
N3—C2	1.412 (2)	C15—H15	0.9300
N3—H3	0.8600	C16—H16	0.9300
N4—C17	1.3703 (19)	S1'—C16'	1.728 (10)
N4—N5	1.4023 (17)	C14'—C15'	1.336 (8)
N4—C21	1.413 (2)	C14'—H14'	0.9300
N5—C19	1.299 (2)	C15'—C16'	1.336 (8)
C1—C2	1.432 (2)	C15'—H15'	0.9300
C2—C3	1.355 (2)	C16'—H16'	0.9300
C3—C4	1.480 (2)	C17—C18	1.434 (2)
C4—H4A	0.9600	C18—C19	1.446 (2)
C4—H4B	0.9600	C19—C20	1.498 (2)
C4—H4C	0.9600	C20—H20A	0.9600
C5—C10	1.380 (2)	C20—H20B	0.9600
C5—C6	1.383 (2)	C20—H20C	0.9600
C6—C7	1.382 (3)	C21—C26	1.386 (2)
C6—H6	0.9300	C21—C22	1.387 (2)
C7—C8	1.368 (3)	C22—C23	1.382 (3)
C7—H7	0.9300	C22—H22	0.9300
C8—C9	1.371 (3)	C23—C24	1.380 (3)
C8—H8	0.9300	C23—H23	0.9300
C9—C10	1.382 (3)	C24—C25	1.370 (3)
C9—H9	0.9300	C24—H24	0.9300
C10—H10	0.9300	C25—C26	1.376 (3)
C11—H11A	0.9600	C25—H25	0.9300
C11—H11B	0.9600	C26—H26	0.9300
C11—H11C	0.9600
C1—N1—N2	109.46 (11)	C18—C12—C13	123.81 (13)
C1—N1—C5	123.58 (12)	C13—S1—C16	91.47 (12)
N2—N1—C5	118.79 (12)	C14—C13—C12	132.40 (16)
C3—N2—N1	106.84 (11)	C14—C13—S1	108.14 (15)
C3—N2—C11	123.14 (13)	C12—C13—S1	119.45 (12)
N1—N2—C11	118.55 (12)	C13—C14—C15	117.3 (3)
C12—N3—C2	125.74 (14)	C13—C14—H14	121.3
C12—N3—H3	117.1	C15—C14—H14	121.3
C2—N3—H3	117.1	C16—C15—C14	111.6 (3)
C17—N4—N5	111.56 (13)	C16—C15—H15	124.2
C17—N4—C21	128.95 (13)	C14—C15—H15	124.2
N5—N4—C21	119.43 (12)	C15—C16—S1	111.5 (3)
C19—N5—N4	106.83 (12)	C15—C16—H16	124.2
O1—C1—N1	124.12 (14)	S1—C16—H16	124.2
O1—C1—C2	131.66 (14)	C15'—C14'—H14'	122.8
N1—C1—C2	104.21 (12)	C16'—C15'—C14'	111.7 (12)
C3—C2—N3	125.48 (14)	C16'—C15'—H15'	124.1
C3—C2—C1	109.25 (13)	C14'—C15'—H15'	124.1
N3—C2—C1	125.25 (13)	C15'—C16'—S1'	112.5 (11)
C2—C3—N2	109.66 (13)	C15'—C16'—H16'	123.7
C2—C3—C4	128.65 (15)	S1'—C16'—H16'	123.7
N2—C3—C4	121.65 (14)	O2—C17—N4	125.97 (15)
C3—C4—H4A	109.5	O2—C17—C18	128.66 (14)
C3—C4—H4B	109.5	N4—C17—C18	105.36 (12)
H4A—C4—H4B	109.5	C12—C18—C17	122.15 (13)
C3—C4—H4C	109.5	C12—C18—C19	132.96 (15)
H4A—C4—H4C	109.5	C17—C18—C19	104.85 (13)
H4B—C4—H4C	109.5	N5—C19—C18	111.29 (14)
C10—C5—C6	120.45 (17)	N5—C19—C20	119.07 (14)
C10—C5—N1	121.06 (15)	C18—C19—C20	129.57 (16)
C6—C5—N1	118.48 (15)	C19—C20—H20A	109.5
C7—C6—C5	119.67 (19)	C19—C20—H20B	109.5
C7—C6—H6	120.2	H20A—C20—H20B	109.5
C5—C6—H6	120.2	C19—C20—H20C	109.5
C8—C7—C6	119.8 (2)	H20A—C20—H20C	109.5
C8—C7—H7	120.1	H20B—C20—H20C	109.5
C6—C7—H7	120.1	C26—C21—C22	119.95 (16)
C7—C8—C9	120.6 (2)	C26—C21—N4	119.76 (15)
C7—C8—H8	119.7	C22—C21—N4	120.29 (14)
C9—C8—H8	119.7	C23—C22—C21	119.30 (16)
C8—C9—C10	120.4 (2)	C23—C22—H22	120.3
C8—C9—H9	119.8	C21—C22—H22	120.3
C10—C9—H9	119.8	C24—C23—C22	120.84 (18)
C5—C10—C9	119.1 (2)	C24—C23—H23	119.6
C5—C10—H10	120.5	C22—C23—H23	119.6
C9—C10—H10	120.5	C25—C24—C23	119.24 (18)
N2—C11—H11A	109.5	C25—C24—H24	120.4
N2—C11—H11B	109.5	C23—C24—H24	120.4
H11A—C11—H11B	109.5	C24—C25—C26	121.12 (17)
N2—C11—H11C	109.5	C24—C25—H25	119.4
H11A—C11—H11C	109.5	C26—C25—H25	119.4
H11B—C11—H11C	109.5	C25—C26—C21	119.55 (17)
N3—C12—C18	118.10 (14)	C25—C26—H26	120.2
N3—C12—C13	118.08 (14)	C21—C26—H26	120.2
C1—N1—N2—C3	7.51 (15)	N3—C12—C13—S1	−109.04 (14)
C5—N1—N2—C3	157.23 (12)	C18—C12—C13—S1	69.48 (18)
C1—N1—N2—C11	152.10 (15)	C16—S1—C13—C14	0.23 (16)
C5—N1—N2—C11	−58.19 (19)	C16—S1—C13—C12	179.22 (18)
C17—N4—N5—C19	−2.41 (18)	C12—C13—C14—C15	−179.3 (2)
C21—N4—N5—C19	−179.86 (14)	S1—C13—C14—C15	−0.51 (16)
N2—N1—C1—O1	174.18 (15)	C13—C14—C15—C16	0.6 (2)
C5—N1—C1—O1	26.2 (2)	C14—C15—C16—S1	−0.4 (2)
N2—N1—C1—C2	−4.47 (15)	C13—S1—C16—C15	0.1 (2)
C5—N1—C1—C2	−152.43 (14)	C14'—C15'—C16'—S1'	−1.0 (5)
C12—N3—C2—C3	97.57 (19)	N5—N4—C17—O2	−175.43 (15)
C12—N3—C2—C1	−84.5 (2)	C21—N4—C17—O2	1.7 (3)
O1—C1—C2—C3	−178.69 (17)	N5—N4—C17—C18	3.33 (16)
N1—C1—C2—C3	−0.18 (16)	C21—N4—C17—C18	−179.53 (14)
O1—C1—C2—N3	3.1 (3)	N3—C12—C18—C17	4.9 (2)
N1—C1—C2—N3	−178.36 (13)	C13—C12—C18—C17	−173.64 (14)
N3—C2—C3—N2	−176.91 (13)	N3—C12—C18—C19	−172.35 (16)
C1—C2—C3—N2	4.92 (17)	C13—C12—C18—C19	9.1 (3)
N3—C2—C3—C4	5.7 (3)	O2—C17—C18—C12	−2.1 (3)
C1—C2—C3—C4	−172.46 (16)	N4—C17—C18—C12	179.21 (14)
N1—N2—C3—C2	−7.60 (16)	O2—C17—C18—C19	175.83 (16)
C11—N2—C3—C2	−150.16 (14)	N4—C17—C18—C19	−2.88 (16)
N1—N2—C3—C4	170.00 (14)	N4—N5—C19—C18	0.41 (18)
C11—N2—C3—C4	27.4 (2)	N4—N5—C19—C20	177.69 (15)
C1—N1—C5—C10	117.51 (17)	C12—C18—C19—N5	179.15 (16)
N2—N1—C5—C10	−27.7 (2)	C17—C18—C19—N5	1.57 (18)
C1—N1—C5—C6	−63.0 (2)	C12—C18—C19—C20	2.2 (3)
N2—N1—C5—C6	151.78 (13)	C17—C18—C19—C20	−175.35 (18)
C10—C5—C6—C7	−0.2 (2)	C17—N4—C21—C26	−158.43 (15)
N1—C5—C6—C7	−179.70 (14)	N5—N4—C21—C26	18.5 (2)
C5—C6—C7—C8	1.3 (3)	C17—N4—C21—C22	21.8 (2)
C6—C7—C8—C9	−0.7 (3)	N5—N4—C21—C22	−161.24 (15)
C7—C8—C9—C10	−1.0 (3)	C26—C21—C22—C23	0.1 (3)
C6—C5—C10—C9	−1.4 (3)	N4—C21—C22—C23	179.81 (15)
N1—C5—C10—C9	178.03 (16)	C21—C22—C23—C24	0.3 (3)
C8—C9—C10—C5	2.0 (3)	C22—C23—C24—C25	−0.4 (3)
C2—N3—C12—C18	−174.54 (14)	C23—C24—C25—C26	0.2 (3)
C2—N3—C12—C13	4.1 (2)	C24—C25—C26—C21	0.1 (3)
N3—C12—C13—C14	69.7 (2)	C22—C21—C26—C25	−0.2 (2)
C18—C12—C13—C14	−111.8 (2)	N4—C21—C26—C25	−179.99 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O2	0.86	1.96	2.6631 (18)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O2	0.86	1.96	2.6631 (18)	138