(Z)-4-(2-Hy-droxy-benzyl-idene)-1-methyl-2-phenyl-1H-imidazol-5(4H)-one.

In the title compound, C(17)H(14)N(2)O(2), the asymmetric unit comprises two mol-ecules that are comformationally similar [the dihedral angles between the phenyl rings in each are 46.35 (2) and 48.04 (3)°], with the conformation stabilized by intra-molecular O-H⋯N hydrogen bonds, which generate S(7) rings. In the crystal, inversion-related mol-ecules are linked by pairs of weak C-H⋯O hydrogen bonds, forming dimers with an R(2) (2)(16) graph-set motif. Weak inter-ring π-π stacking is observed in the structure, the shortest centroid-to-centroid distance being 3.7480 (13) Å.

Related literature

For the spectroscopy and preparation of the title compound, see: Chuang et al. (2011 ▶). For the applications of proton-transfer dyes, see: Chen & Pang (2010 ▶); Gryko et al. (2010 ▶); Han et al. (2010 ▶); Helal et al. (2010 ▶); Ikeda et al. (2010 ▶); Ito et al. (2011 ▶); Lim et al. (2011 ▶); Lins et al. (2010 ▶); Maupin et al. (2011 ▶); Santos et al. (2011 ▶); Tang et al. (2011 ▶). For a related structure, see: Chen et al. (2007 ▶). For graph-set theory of hydrogen bonds, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C17H14N2O2

M = 278.30

Triclinic,

a = 9.7843 (4) Å

b = 9.8972 (3) Å

c = 15.4313 (6) Å

α = 72.086 (2)°

β = 79.301 (2)°

γ = 70.500 (2)°

V = 1334.57 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 150 K

0.32 × 0.28 × 0.14 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.889, T max = 0.984

20392 measured reflections

4699 independent reflections

2273 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.101

S = 0.80

4699 reflections

382 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.36 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; 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, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812007921/zs2183sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007921/zs2183Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812007921/zs2183Isup3.cml

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

C17H14N2O2	Z = 4
Mr = 278.30	F(000) = 584
Triclinic, P1	Dx = 1.385 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7843 (4) Å	Cell parameters from 3314 reflections
b = 9.8972 (3) Å	θ = 2.5–25.0°
c = 15.4313 (6) Å	µ = 0.09 mm−1
α = 72.086 (2)°	T = 150 K
β = 79.301 (2)°	Prism, yellow
γ = 70.500 (2)°	0.32 × 0.28 × 0.14 mm
V = 1334.57 (9) Å3

Bruker SMART CCD diffractometer	4699 independent reflections
Radiation source: fine-focus sealed tube	2273 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
φ and ω scans	θmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→11
Tmin = 0.889, Tmax = 0.984	k = −11→10
20392 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)] = 0.037	H-atom parameters constrained
wR(F2) = 0.101	w = 1/[σ2(Fo2) + (0.049P)2] where P = (Fo2 + 2Fc2)/3
S = 0.80	(Δ/σ)max < 0.001
4699 reflections	Δρmax = 0.35 e Å−3
382 parameters	Δρmin = −0.36 e Å−3
0 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: 0.037 (2)

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
O1	0.13687 (16)	−0.12970 (16)	0.02374 (11)	0.0292 (4)
O2	0.24941 (16)	0.01412 (16)	0.32193 (9)	0.0331 (5)
H2	0.1962	−0.0125	0.2996	0.050*
O3	0.15388 (16)	0.37862 (16)	0.01672 (11)	0.0299 (4)
O4	0.23819 (17)	0.52664 (17)	0.32188 (10)	0.0410 (5)
H4	0.1961	0.4877	0.2999	0.061*
N1	−0.00550 (19)	−0.16641 (18)	0.16225 (12)	0.0229 (5)
N2	0.09021 (19)	−0.07230 (18)	0.24367 (12)	0.0219 (5)
N3	0.00423 (19)	0.34215 (18)	0.15218 (12)	0.0228 (5)
N4	0.10847 (19)	0.41218 (18)	0.24187 (12)	0.0227 (5)
C1	−0.0086 (2)	−0.1355 (2)	0.24468 (15)	0.0223 (6)
C2	0.1046 (2)	−0.1190 (2)	0.10228 (16)	0.0227 (6)
C3	0.1655 (2)	−0.0577 (2)	0.15660 (15)	0.0206 (6)
C4	−0.1125 (2)	−0.2116 (2)	0.13239 (15)	0.0306 (6)
H4A	−0.1132	−0.1750	0.0671	0.046*
H4B	−0.2073	−0.1713	0.1609	0.046*
H4C	−0.0875	−0.3181	0.1495	0.046*
C5	0.2778 (2)	−0.0006 (2)	0.12414 (15)	0.0215 (6)
H5	0.3074	0.0033	0.0628	0.026*
C6	0.3625 (2)	0.0560 (2)	0.16442 (15)	0.0193 (6)
C7	0.3494 (2)	0.0583 (2)	0.25650 (16)	0.0232 (6)
C8	0.4470 (3)	0.1070 (2)	0.28520 (16)	0.0307 (7)
H8	0.4385	0.1081	0.3460	0.037*
C9	0.5556 (3)	0.1535 (2)	0.22577 (16)	0.0312 (7)
H9	0.6200	0.1846	0.2469	0.037*
C10	0.5697 (2)	0.1544 (2)	0.13480 (16)	0.0288 (6)
H10	0.6424	0.1868	0.0941	0.035*
C11	0.4740 (2)	0.1065 (2)	0.10597 (15)	0.0251 (6)
H11	0.4834	0.1074	0.0447	0.030*
C13	−0.1095 (2)	−0.1721 (2)	0.32475 (15)	0.0213 (6)
C14	−0.1679 (2)	−0.0741 (2)	0.37879 (15)	0.0259 (6)
H14	−0.1459	0.0154	0.3627	0.031*
C15	−0.2590 (2)	−0.1091 (2)	0.45685 (16)	0.0316 (7)
H15	−0.2995	−0.0424	0.4925	0.038*
C16	−0.2899 (3)	−0.2423 (3)	0.48168 (16)	0.0335 (7)
H16	−0.3511	−0.2654	0.5342	0.040*
C17	−0.2304 (3)	−0.3420 (3)	0.42909 (17)	0.0403 (7)
H17	−0.2504	−0.4327	0.4465	0.048*
C18	−0.1414 (3)	−0.3063 (2)	0.35063 (16)	0.0342 (7)
H18	−0.1023	−0.3729	0.3147	0.041*
C21	0.0052 (2)	0.3587 (2)	0.23784 (15)	0.0213 (6)
C22	0.1193 (2)	0.3853 (2)	0.09563 (16)	0.0224 (6)
C23	0.1837 (2)	0.4354 (2)	0.15464 (15)	0.0218 (6)
C24	−0.0927 (2)	0.2851 (2)	0.12174 (15)	0.0300 (6)
H24A	−0.0467	0.2512	0.0685	0.045*
H24B	−0.1819	0.3626	0.1071	0.045*
H24C	−0.1133	0.2037	0.1696	0.045*
C25	0.2933 (2)	0.4973 (2)	0.12575 (15)	0.0241 (6)
H25	0.3284	0.5009	0.0650	0.029*
C26	0.3682 (2)	0.5595 (2)	0.16923 (16)	0.0219 (6)
C27	0.3378 (2)	0.5747 (2)	0.25873 (16)	0.0238 (6)
C28	0.4158 (3)	0.6439 (2)	0.28910 (16)	0.0288 (6)
H28	0.3938	0.6553	0.3482	0.035*
C29	0.5248 (3)	0.6955 (2)	0.23309 (17)	0.0314 (7)
H29	0.5759	0.7410	0.2544	0.038*
C30	0.5579 (2)	0.6795 (2)	0.14511 (17)	0.0319 (7)
H30	0.6319	0.7136	0.1071	0.038*
C31	0.4811 (2)	0.6132 (2)	0.11422 (16)	0.0289 (6)
H31	0.5042	0.6032	0.0548	0.035*
C33	−0.0964 (2)	0.3198 (2)	0.31732 (15)	0.0221 (6)
C34	−0.0444 (3)	0.2553 (2)	0.40301 (16)	0.0295 (6)
H34	0.0537	0.2357	0.4088	0.035*
C35	−0.1373 (3)	0.2200 (2)	0.47980 (16)	0.0334 (7)
H35	−0.1012	0.1757	0.5368	0.040*
C36	−0.2833 (3)	0.2502 (2)	0.47222 (16)	0.0290 (6)
H36	−0.3458	0.2261	0.5239	0.035*
C37	−0.3360 (3)	0.3161 (2)	0.38798 (16)	0.0282 (6)
H37	−0.4348	0.3376	0.3830	0.034*
C38	−0.2438 (2)	0.3510 (2)	0.31025 (15)	0.0254 (6)
H38	−0.2807	0.3952	0.2535	0.030*

	U11	U22	U33	U12	U13	U23
O1	0.0265 (10)	0.0404 (10)	0.0249 (11)	−0.0125 (8)	0.0015 (8)	−0.0138 (9)
O2	0.0353 (11)	0.0523 (11)	0.0223 (10)	−0.0289 (9)	0.0055 (9)	−0.0123 (8)
O3	0.0312 (11)	0.0353 (10)	0.0240 (11)	−0.0109 (9)	0.0004 (9)	−0.0096 (9)
O4	0.0483 (12)	0.0557 (12)	0.0318 (11)	−0.0307 (10)	0.0043 (10)	−0.0175 (9)
N1	0.0195 (12)	0.0289 (12)	0.0253 (13)	−0.0123 (10)	0.0000 (10)	−0.0099 (10)
N2	0.0184 (12)	0.0245 (11)	0.0230 (13)	−0.0092 (10)	0.0017 (10)	−0.0055 (9)
N3	0.0228 (13)	0.0275 (12)	0.0217 (12)	−0.0112 (10)	−0.0014 (10)	−0.0079 (10)
N4	0.0206 (12)	0.0259 (11)	0.0228 (13)	−0.0098 (10)	0.0011 (10)	−0.0068 (9)
C1	0.0199 (15)	0.0205 (14)	0.0256 (16)	−0.0033 (12)	−0.0017 (12)	−0.0078 (12)
C2	0.0187 (15)	0.0232 (14)	0.0241 (16)	−0.0041 (12)	−0.0015 (13)	−0.0061 (12)
C3	0.0170 (14)	0.0212 (13)	0.0217 (15)	−0.0042 (11)	−0.0019 (12)	−0.0044 (11)
C4	0.0265 (16)	0.0392 (16)	0.0340 (17)	−0.0156 (13)	−0.0043 (13)	−0.0136 (13)
C5	0.0208 (15)	0.0233 (14)	0.0171 (14)	−0.0032 (12)	−0.0008 (11)	−0.0049 (11)
C6	0.0164 (14)	0.0186 (13)	0.0208 (15)	−0.0044 (11)	−0.0010 (12)	−0.0036 (11)
C7	0.0217 (15)	0.0229 (14)	0.0244 (16)	−0.0086 (12)	0.0017 (12)	−0.0054 (12)
C8	0.0332 (16)	0.0412 (16)	0.0242 (16)	−0.0164 (14)	−0.0004 (13)	−0.0133 (13)
C9	0.0283 (16)	0.0406 (16)	0.0325 (17)	−0.0189 (13)	−0.0029 (13)	−0.0113 (13)
C10	0.0197 (15)	0.0357 (15)	0.0334 (17)	−0.0145 (13)	0.0025 (13)	−0.0084 (13)
C11	0.0227 (15)	0.0282 (14)	0.0239 (15)	−0.0070 (12)	0.0010 (12)	−0.0084 (12)
C13	0.0176 (14)	0.0243 (14)	0.0231 (15)	−0.0084 (12)	−0.0009 (12)	−0.0058 (12)
C14	0.0264 (15)	0.0258 (14)	0.0269 (15)	−0.0106 (12)	−0.0003 (12)	−0.0068 (12)
C15	0.0316 (16)	0.0329 (16)	0.0312 (17)	−0.0101 (13)	0.0045 (13)	−0.0135 (13)
C16	0.0296 (17)	0.0405 (16)	0.0319 (17)	−0.0190 (14)	0.0078 (13)	−0.0086 (14)
C17	0.0440 (18)	0.0402 (17)	0.0427 (18)	−0.0269 (15)	0.0126 (15)	−0.0134 (14)
C18	0.0376 (17)	0.0318 (16)	0.0386 (17)	−0.0162 (13)	0.0071 (14)	−0.0166 (13)
C21	0.0220 (15)	0.0184 (14)	0.0222 (16)	−0.0052 (12)	−0.0017 (12)	−0.0048 (12)
C22	0.0222 (15)	0.0193 (14)	0.0215 (16)	−0.0027 (11)	−0.0011 (13)	−0.0038 (12)
C23	0.0192 (14)	0.0233 (14)	0.0210 (15)	−0.0058 (12)	0.0015 (12)	−0.0057 (12)
C24	0.0318 (16)	0.0322 (15)	0.0303 (16)	−0.0111 (13)	−0.0054 (13)	−0.0109 (12)
C25	0.0229 (15)	0.0230 (14)	0.0227 (15)	−0.0039 (12)	0.0026 (12)	−0.0068 (12)
C26	0.0202 (15)	0.0194 (14)	0.0256 (16)	−0.0047 (12)	−0.0013 (12)	−0.0073 (12)
C27	0.0217 (15)	0.0236 (14)	0.0243 (16)	−0.0090 (12)	0.0012 (12)	−0.0032 (12)
C28	0.0324 (16)	0.0286 (14)	0.0257 (16)	−0.0059 (13)	−0.0073 (13)	−0.0081 (12)
C29	0.0250 (16)	0.0274 (15)	0.0443 (19)	−0.0077 (13)	−0.0107 (14)	−0.0087 (14)
C30	0.0205 (15)	0.0297 (15)	0.0430 (19)	−0.0080 (12)	0.0009 (13)	−0.0080 (14)
C31	0.0249 (16)	0.0252 (14)	0.0363 (17)	−0.0089 (12)	−0.0019 (13)	−0.0066 (13)
C33	0.0229 (15)	0.0215 (14)	0.0234 (16)	−0.0087 (12)	−0.0009 (12)	−0.0068 (12)
C34	0.0245 (15)	0.0384 (16)	0.0283 (16)	−0.0130 (13)	−0.0031 (13)	−0.0080 (13)
C35	0.0361 (17)	0.0436 (17)	0.0226 (16)	−0.0178 (14)	−0.0025 (13)	−0.0050 (13)
C36	0.0299 (17)	0.0327 (15)	0.0253 (16)	−0.0139 (13)	0.0061 (13)	−0.0091 (13)
C37	0.0207 (15)	0.0283 (15)	0.0354 (17)	−0.0094 (12)	0.0015 (13)	−0.0079 (13)
C38	0.0248 (15)	0.0257 (14)	0.0248 (15)	−0.0080 (12)	−0.0035 (12)	−0.0043 (12)

O1—C2	1.222 (2)	C14—H14	0.9300
O2—C7	1.347 (2)	C15—C16	1.373 (3)
O2—H2	0.8200	C15—H15	0.9300
O3—C22	1.218 (2)	C16—C17	1.380 (3)
O4—C27	1.341 (2)	C16—H16	0.9300
O4—H4	0.8200	C17—C18	1.378 (3)
N1—C2	1.392 (3)	C17—H17	0.9300
N1—C1	1.390 (3)	C18—H18	0.9300
N1—C4	1.458 (2)	C21—C33	1.467 (3)
N2—C1	1.311 (2)	C22—C23	1.474 (3)
N2—C3	1.397 (3)	C23—C25	1.348 (3)
N3—C21	1.383 (3)	C24—H24A	0.9600
N3—C22	1.392 (3)	C24—H24B	0.9600
N3—C24	1.458 (2)	C24—H24C	0.9600
N4—C21	1.306 (2)	C25—C26	1.450 (3)
N4—C23	1.400 (3)	C25—H25	0.9300
C1—C13	1.464 (3)	C26—C27	1.402 (3)
C2—C3	1.471 (3)	C26—C31	1.410 (3)
C3—C5	1.347 (3)	C27—C28	1.396 (3)
C4—H4A	0.9600	C28—C29	1.376 (3)
C4—H4B	0.9600	C28—H28	0.9300
C4—H4C	0.9600	C29—C30	1.381 (3)
C5—C6	1.449 (3)	C29—H29	0.9300
C5—H5	0.9300	C30—C31	1.371 (3)
C6—C11	1.406 (3)	C30—H30	0.9300
C6—C7	1.409 (3)	C31—H31	0.9300
C7—C8	1.392 (3)	C33—C34	1.388 (3)
C8—C9	1.374 (3)	C33—C38	1.389 (3)
C8—H8	0.9300	C34—C35	1.382 (3)
C9—C10	1.382 (3)	C34—H34	0.9300
C9—H9	0.9300	C35—C36	1.378 (3)
C10—C11	1.372 (3)	C35—H35	0.9300
C10—H10	0.9300	C36—C37	1.373 (3)
C11—H11	0.9300	C36—H36	0.9300
C13—C14	1.383 (3)	C37—C38	1.387 (3)
C13—C18	1.388 (3)	C37—H37	0.9300
C14—C15	1.385 (3)	C38—H38	0.9300
C7—O2—H2	109.5	C18—C17—H17	120.2
C27—O4—H4	109.5	C16—C17—H17	120.2
C2—N1—C1	108.23 (18)	C17—C18—C13	120.6 (2)
C2—N1—C4	122.40 (19)	C17—C18—H18	119.7
C1—N1—C4	128.31 (19)	C13—C18—H18	119.7
C1—N2—C3	106.55 (18)	N4—C21—N3	112.87 (19)
C21—N3—C22	108.32 (18)	N4—C21—C33	122.4 (2)
C21—N3—C24	128.78 (18)	N3—C21—C33	124.7 (2)
C22—N3—C24	122.86 (19)	O3—C22—N3	125.6 (2)
C21—N4—C23	106.86 (19)	O3—C22—C23	130.9 (2)
N2—C1—N1	112.80 (19)	N3—C22—C23	103.46 (19)
N2—C1—C13	123.5 (2)	C25—C23—N4	127.5 (2)
N1—C1—C13	123.68 (19)	C25—C23—C22	124.1 (2)
O1—C2—N1	125.2 (2)	N4—C23—C22	108.41 (18)
O1—C2—C3	131.3 (2)	N3—C24—H24A	109.5
N1—C2—C3	103.43 (19)	N3—C24—H24B	109.5
C5—C3—N2	128.0 (2)	H24A—C24—H24B	109.5
C5—C3—C2	123.0 (2)	N3—C24—H24C	109.5
N2—C3—C2	108.99 (18)	H24A—C24—H24C	109.5
N1—C4—H4A	109.5	H24B—C24—H24C	109.5
N1—C4—H4B	109.5	C23—C25—C26	133.6 (2)
H4A—C4—H4B	109.5	C23—C25—H25	113.2
N1—C4—H4C	109.5	C26—C25—H25	113.2
H4A—C4—H4C	109.5	C27—C26—C31	117.1 (2)
H4B—C4—H4C	109.5	C27—C26—C25	126.9 (2)
C3—C5—C6	133.7 (2)	C31—C26—C25	115.9 (2)
C3—C5—H5	113.2	O4—C27—C28	114.2 (2)
C6—C5—H5	113.2	O4—C27—C26	125.9 (2)
C11—C6—C7	117.1 (2)	C28—C27—C26	120.0 (2)
C11—C6—C5	116.0 (2)	C29—C28—C27	121.1 (2)
C7—C6—C5	126.9 (2)	C29—C28—H28	119.4
O2—C7—C8	115.5 (2)	C27—C28—H28	119.4
O2—C7—C6	125.2 (2)	C28—C29—C30	119.8 (2)
C8—C7—C6	119.3 (2)	C28—C29—H29	120.1
C9—C8—C7	121.5 (2)	C30—C29—H29	120.1
C9—C8—H8	119.2	C31—C30—C29	119.5 (2)
C7—C8—H8	119.2	C31—C30—H30	120.2
C8—C9—C10	120.4 (2)	C29—C30—H30	120.2
C8—C9—H9	119.8	C30—C31—C26	122.4 (2)
C10—C9—H9	119.8	C30—C31—H31	118.8
C11—C10—C9	118.4 (2)	C26—C31—H31	118.8
C11—C10—H10	120.8	C34—C33—C38	118.9 (2)
C9—C10—H10	120.8	C34—C33—C21	118.9 (2)
C10—C11—C6	123.3 (2)	C38—C33—C21	122.2 (2)
C10—C11—H11	118.4	C35—C34—C33	120.6 (2)
C6—C11—H11	118.4	C35—C34—H34	119.7
C14—C13—C18	119.2 (2)	C33—C34—H34	119.7
C14—C13—C1	119.10 (19)	C36—C35—C34	120.2 (2)
C18—C13—C1	121.6 (2)	C36—C35—H35	119.9
C13—C14—C15	120.1 (2)	C34—C35—H35	119.9
C13—C14—H14	119.9	C37—C36—C35	119.6 (2)
C15—C14—H14	119.9	C37—C36—H36	120.2
C16—C15—C14	120.1 (2)	C35—C36—H36	120.2
C16—C15—H15	119.9	C36—C37—C38	120.8 (2)
C14—C15—H15	119.9	C36—C37—H37	119.6
C15—C16—C17	120.3 (2)	C38—C37—H37	119.6
C15—C16—H16	119.8	C33—C38—C37	119.9 (2)
C17—C16—H16	119.8	C33—C38—H38	120.1
C18—C17—C16	119.6 (2)	C37—C38—H38	120.1
C2—N1—C1—N2	−0.1 (2)	C3—C5—C6—C7	3.3 (4)
C2—N1—C1—C13	−179.03 (19)	C3—C5—C6—C11	179.8 (2)
C4—N1—C1—N2	−168.39 (19)	C5—C6—C7—O2	−3.5 (3)
C1—N1—C2—O1	179.9 (2)	C5—C6—C7—C8	175.3 (2)
C1—N1—C2—C3	0.0 (2)	C11—C6—C7—O2	−179.95 (18)
C4—N1—C2—O1	−11.0 (3)	C11—C6—C7—C8	−1.1 (3)
C4—N1—C2—C3	169.06 (17)	C5—C6—C11—C10	−175.71 (19)
C3—N2—C1—N1	0.3 (2)	C7—C6—C11—C10	1.1 (3)
C3—N2—C1—C13	179.15 (19)	O2—C7—C8—C9	179.22 (19)
C1—N2—C3—C2	−0.3 (2)	C6—C7—C8—C9	0.3 (3)
C1—N2—C3—C5	−179.1 (2)	C7—C8—C9—C10	0.7 (3)
N1—C1—C13—C14	−142.3 (2)	C8—C9—C10—C11	−0.7 (3)
N1—C1—C13—C18	41.4 (3)	C9—C10—C11—C6	−0.2 (3)
N2—C1—C13—C14	38.9 (3)	C1—C13—C14—C15	−177.4 (2)
N2—C1—C13—C18	−137.4 (2)	C18—C13—C14—C15	−1.1 (3)
O1—C2—C3—N2	−179.8 (2)	C1—C13—C18—C17	176.4 (2)
O1—C2—C3—C5	−0.8 (4)	C14—C13—C18—C17	0.1 (4)
N1—C2—C3—N2	0.2 (2)	C13—C14—C15—C16	1.0 (3)
N1—C2—C3—C5	179.09 (19)	C14—C15—C16—C17	0.0 (4)
N2—C3—C5—C6	3.6 (4)	C15—C16—C17—C18	−1.0 (4)
C2—C3—C5—C6	−175.1 (2)	C16—C17—C18—C13	0.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2	0.82	1.80	2.615 (2)	176
O4—H4···N4	0.82	1.79	2.612 (3)	175
C4—H4A···O1	0.96	2.56	2.896 (3)	100
C10—H10···O1i	0.93	2.58	3.403 (3)	148
C30—H30···O3ii	0.93	2.68	3.421 (3)	137
C24—H24A···O3	0.96	2.56	2.902 (3)	101

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N2	0.82	1.80	2.615 (2)	176
O4—H4⋯N4	0.82	1.79	2.612 (3)	175
C10—H10⋯O1i	0.93	2.58	3.403 (3)	148
C30—H30⋯O3ii	0.93	2.68	3.421 (3)	137

Symmetry codes: (i) ; (ii) .