2-(3-Cyano-4-{7-[1-(2-hy-droxy-eth-yl)-3,3-dimethyl-indolin-2-yl-idene]hepta-1,3,5-trien-yl}-5,5-dimethyl-2,5-dihydro-furan-2-yl-idene)malononitrile.

The title compound, C(29)H(28)N(4)O(2), excluding the hydroxyethyl and methyl groups, is slightly twisted from planarity so that the terminating indol-2-yl-idene and furan-2-yl-idene moiety planes subtend a dihedral angle of 6.27 (8)°. A small inwards fold in the polymethine atom chain is consistent with centrosymmetric dimer formation via O-H⋯N(cyano) hydrogen bonds. In the crystal, the mol-ecules pack in layers approximately parallel to the (10[Formula: see text]) plane via pairs of O-H⋯N and C-H⋯N(cyano) inter-actions.

Related literature

For general background to NLO chromophores containing an indoline donor with a 2-(3-cyano-4,5,5-trimethyl-5H-furan-2-yl­idene)-malontrile unit, see Gainsford et al. (2007 ▶, 2008 ▶, 2009 ▶). For closely related structures, see Bhuiyan et al. (2011 ▶). For hydrogen-motifs see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C29H28N4O2

M = 464.55

Triclinic,

a = 9.3157 (4) Å

b = 10.5376 (4) Å

c = 13.4474 (6) Å

α = 101.338 (2)°

β = 100.087 (2)°

γ = 100.570 (2)°

V = 1241.42 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 124 K

0.57 × 0.38 × 0.18 mm

Data collection

Nonius APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.642, T max = 0.746

34665 measured reflections

7739 independent reflections

5982 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.130

S = 1.02

7739 reflections

323 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); 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 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009) ▶ and Mercury.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811042036/im2321sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042036/im2321Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811042036/im2321Isup3.cml

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

C29H28N4O2	Z = 2
Mr = 464.55	F(000) = 492
Triclinic, P1	Dx = 1.243 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3157 (4) Å	Cell parameters from 9900 reflections
b = 10.5376 (4) Å	θ = 2.3–31.0°
c = 13.4474 (6) Å	µ = 0.08 mm−1
α = 101.338 (2)°	T = 124 K
β = 100.087 (2)°	Triangular, green
γ = 100.570 (2)°	0.57 × 0.38 × 0.18 mm
V = 1241.42 (9) Å3

Nonius APEXII CCD area-detector diffractometer	7739 independent reflections
Radiation source: fine-focus sealed tube	5982 reflections with I > 2σ(I)
graphite	Rint = 0.034
Detector resolution: 8.192 pixels mm-1	θmax = 31.0°, θmin = 1.6°
φ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2006)	k = −15→15
Tmin = 0.642, Tmax = 0.746	l = −19→19
34665 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0718P)2 + 0.2125P] where P = (Fo2 + 2Fc2)/3
7739 reflections	(Δ/σ)max = 0.001
323 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.20 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
O1	0.71795 (8)	0.82289 (7)	0.92717 (6)	0.02507 (16)
O2	−0.35065 (10)	−0.26989 (9)	0.19623 (8)	0.0373 (2)
H2O	−0.4383 (19)	−0.2514 (16)	0.1842 (13)	0.045*
N1	0.66590 (15)	1.24644 (11)	0.87339 (10)	0.0448 (3)
N2	0.93528 (13)	1.09871 (10)	1.10997 (9)	0.0392 (3)
N3	0.45206 (12)	0.98613 (11)	0.66154 (9)	0.0366 (2)
N4	−0.02761 (10)	−0.24219 (8)	0.24132 (7)	0.02330 (18)
C1	0.70116 (13)	1.15797 (11)	0.90100 (9)	0.0303 (2)
C2	0.74324 (12)	1.04986 (10)	0.93699 (9)	0.0257 (2)
C3	0.84953 (13)	1.07704 (10)	1.03239 (9)	0.0284 (2)
C4	0.55395 (11)	0.72345 (10)	0.76525 (8)	0.02158 (19)
C5	0.64214 (11)	0.69063 (9)	0.85922 (8)	0.0221 (2)
C6	0.67975 (11)	0.91863 (10)	0.88274 (8)	0.0227 (2)
C7	0.57921 (12)	0.86372 (10)	0.78615 (8)	0.0231 (2)
C8	0.54462 (13)	0.62225 (11)	0.92134 (9)	0.0296 (2)
H8A	0.6078	0.6126	0.9846	0.044*
H8B	0.4896	0.5343	0.8793	0.044*
H8C	0.4735	0.6757	0.9403	0.044*
C9	0.76526 (13)	0.62185 (12)	0.83557 (10)	0.0331 (3)
H9A	0.8286	0.6736	0.7998	0.050*
H9B	0.7210	0.5328	0.7909	0.050*
H9C	0.8260	0.6146	0.9006	0.050*
C10	0.51171 (12)	0.93438 (10)	0.71858 (9)	0.0260 (2)
C11	0.46959 (12)	0.63644 (10)	0.67482 (8)	0.0242 (2)
H11	0.4263	0.6745	0.6218	0.029*
C12	0.44121 (11)	0.49721 (10)	0.65314 (8)	0.0236 (2)
H12	0.4773	0.4566	0.7067	0.028*
C13	0.36367 (11)	0.41618 (10)	0.55813 (8)	0.0236 (2)
H13	0.3289	0.4567	0.5042	0.028*
C14	0.33368 (11)	0.27742 (10)	0.53722 (8)	0.0231 (2)
H14	0.3719	0.2376	0.5906	0.028*
C15	0.25179 (11)	0.19435 (10)	0.44357 (8)	0.0237 (2)
H15	0.2183	0.2325	0.3879	0.028*
C16	0.21690 (11)	0.05615 (10)	0.42834 (8)	0.0239 (2)
H16	0.2631	0.0179	0.4802	0.029*
C17	0.11797 (12)	−0.02769 (10)	0.34110 (8)	0.0245 (2)
H17	0.0762	0.0114	0.2883	0.029*
C18	0.07525 (11)	−0.16581 (10)	0.32523 (8)	0.02182 (19)
C19	0.13282 (11)	−0.25464 (10)	0.39245 (8)	0.02175 (19)
C20	0.03818 (11)	−0.38962 (10)	0.33335 (8)	0.0231 (2)
C21	0.02942 (13)	−0.51323 (11)	0.35538 (9)	0.0282 (2)
H21	0.0881	−0.5230	0.4175	0.034*
C22	−0.06712 (13)	−0.62311 (11)	0.28469 (10)	0.0310 (2)
H22	−0.0736	−0.7088	0.2985	0.037*
C23	−0.15338 (13)	−0.60900 (11)	0.19486 (10)	0.0313 (2)
H23	−0.2172	−0.6856	0.1473	0.038*
C24	−0.14916 (12)	−0.48553 (11)	0.17230 (9)	0.0291 (2)
H24	−0.2096	−0.4754	0.1110	0.035*
C25	−0.05204 (11)	−0.37760 (10)	0.24393 (8)	0.0236 (2)
C26	−0.11143 (12)	−0.19416 (10)	0.15981 (8)	0.0255 (2)
H26A	−0.1409	−0.2645	0.0946	0.031*
H26B	−0.0462	−0.1162	0.1472	0.031*
C27	−0.25032 (13)	−0.15534 (11)	0.18821 (10)	0.0303 (2)
H27A	−0.2226	−0.0883	0.2553	0.036*
H27B	−0.2992	−0.1158	0.1343	0.036*
C28	0.10768 (13)	−0.22202 (12)	0.50358 (9)	0.0312 (2)
H28A	0.0018	−0.2228	0.5011	0.047*
H28B	0.1688	−0.1339	0.5407	0.047*
H28C	0.1365	−0.2886	0.5399	0.047*
C29	0.29911 (11)	−0.25018 (11)	0.39367 (9)	0.0274 (2)
H29A	0.3305	−0.3181	0.4273	0.041*
H29B	0.3593	−0.1623	0.4323	0.041*
H29C	0.3134	−0.2673	0.3222	0.041*

	U11	U22	U33	U12	U13	U23
O1	0.0285 (4)	0.0173 (3)	0.0231 (4)	0.0011 (3)	−0.0028 (3)	0.0013 (3)
O2	0.0313 (4)	0.0392 (5)	0.0459 (5)	0.0108 (4)	0.0072 (4)	0.0191 (4)
N1	0.0584 (7)	0.0291 (5)	0.0429 (7)	0.0147 (5)	−0.0008 (5)	0.0053 (5)
N2	0.0450 (6)	0.0222 (4)	0.0384 (6)	0.0009 (4)	−0.0083 (5)	0.0012 (4)
N3	0.0394 (5)	0.0324 (5)	0.0355 (6)	0.0090 (4)	0.0001 (4)	0.0090 (4)
N4	0.0228 (4)	0.0189 (4)	0.0235 (4)	0.0038 (3)	−0.0027 (3)	0.0018 (3)
C1	0.0355 (6)	0.0228 (5)	0.0280 (6)	0.0067 (4)	0.0021 (4)	−0.0003 (4)
C2	0.0282 (5)	0.0187 (4)	0.0254 (5)	0.0033 (4)	0.0005 (4)	0.0005 (4)
C3	0.0322 (5)	0.0161 (4)	0.0312 (6)	0.0021 (4)	0.0012 (4)	0.0009 (4)
C4	0.0229 (4)	0.0192 (4)	0.0200 (5)	0.0020 (3)	0.0038 (4)	0.0020 (3)
C5	0.0236 (4)	0.0168 (4)	0.0208 (5)	−0.0002 (3)	0.0009 (4)	0.0007 (3)
C6	0.0240 (4)	0.0189 (4)	0.0229 (5)	0.0032 (4)	0.0037 (4)	0.0020 (4)
C7	0.0259 (5)	0.0195 (4)	0.0210 (5)	0.0037 (4)	0.0023 (4)	0.0018 (4)
C8	0.0312 (5)	0.0296 (5)	0.0231 (5)	−0.0034 (4)	0.0020 (4)	0.0074 (4)
C9	0.0277 (5)	0.0281 (5)	0.0380 (6)	0.0076 (4)	0.0015 (5)	−0.0010 (5)
C10	0.0287 (5)	0.0213 (4)	0.0244 (5)	0.0041 (4)	0.0028 (4)	0.0013 (4)
C11	0.0267 (5)	0.0213 (4)	0.0206 (5)	0.0027 (4)	0.0018 (4)	0.0015 (4)
C12	0.0235 (4)	0.0214 (4)	0.0218 (5)	0.0014 (4)	0.0017 (4)	0.0018 (4)
C13	0.0224 (4)	0.0216 (4)	0.0225 (5)	0.0032 (4)	0.0000 (4)	0.0010 (4)
C14	0.0199 (4)	0.0214 (4)	0.0238 (5)	0.0023 (3)	0.0012 (4)	0.0014 (4)
C15	0.0215 (4)	0.0211 (4)	0.0247 (5)	0.0034 (4)	0.0014 (4)	0.0011 (4)
C16	0.0215 (4)	0.0216 (4)	0.0248 (5)	0.0040 (4)	0.0011 (4)	0.0007 (4)
C17	0.0244 (5)	0.0198 (4)	0.0248 (5)	0.0035 (4)	−0.0005 (4)	0.0014 (4)
C18	0.0192 (4)	0.0207 (4)	0.0223 (5)	0.0042 (3)	0.0005 (3)	0.0014 (4)
C19	0.0195 (4)	0.0224 (4)	0.0214 (5)	0.0043 (3)	0.0008 (3)	0.0043 (4)
C20	0.0210 (4)	0.0215 (4)	0.0260 (5)	0.0052 (4)	0.0042 (4)	0.0042 (4)
C21	0.0292 (5)	0.0261 (5)	0.0316 (6)	0.0089 (4)	0.0064 (4)	0.0095 (4)
C22	0.0326 (5)	0.0218 (5)	0.0400 (6)	0.0063 (4)	0.0111 (5)	0.0077 (4)
C23	0.0280 (5)	0.0210 (5)	0.0394 (6)	0.0022 (4)	0.0045 (5)	0.0003 (4)
C24	0.0265 (5)	0.0226 (5)	0.0317 (6)	0.0035 (4)	−0.0018 (4)	0.0005 (4)
C25	0.0218 (4)	0.0187 (4)	0.0275 (5)	0.0041 (4)	0.0019 (4)	0.0028 (4)
C26	0.0273 (5)	0.0232 (5)	0.0223 (5)	0.0050 (4)	−0.0025 (4)	0.0046 (4)
C27	0.0292 (5)	0.0281 (5)	0.0315 (6)	0.0090 (4)	−0.0008 (4)	0.0069 (4)
C28	0.0317 (5)	0.0339 (6)	0.0253 (5)	0.0035 (4)	0.0070 (4)	0.0040 (4)
C29	0.0205 (4)	0.0302 (5)	0.0316 (6)	0.0067 (4)	0.0033 (4)	0.0085 (4)

O1—C6	1.3400 (13)	C14—H14	0.9500
O1—C5	1.4793 (12)	C15—C16	1.3980 (14)
O2—C27	1.4194 (14)	C15—H15	0.9500
O2—H2O	0.869 (17)	C16—C17	1.3861 (14)
N1—C1	1.1491 (16)	C16—H16	0.9500
N2—C3	1.1515 (16)	C17—C18	1.3993 (14)
N3—C10	1.1493 (15)	C17—H17	0.9500
N4—C18	1.3492 (13)	C18—C19	1.5258 (14)
N4—C25	1.4115 (13)	C19—C20	1.5106 (14)
N4—C26	1.4596 (13)	C19—C28	1.5351 (15)
C1—C2	1.4142 (16)	C19—C29	1.5383 (14)
C2—C6	1.3952 (14)	C20—C21	1.3829 (14)
C2—C3	1.4195 (16)	C20—C25	1.3831 (15)
C4—C11	1.3783 (14)	C21—C22	1.3924 (16)
C4—C7	1.4160 (14)	C21—H21	0.9500
C4—C5	1.5178 (14)	C22—C23	1.3790 (18)
C5—C9	1.5114 (16)	C22—H22	0.9500
C5—C8	1.5182 (14)	C23—C24	1.3881 (16)
C6—C7	1.4066 (14)	C23—H23	0.9500
C7—C10	1.4189 (15)	C24—C25	1.3880 (14)
C8—H8A	0.9800	C24—H24	0.9500
C8—H8B	0.9800	C26—C27	1.5142 (16)
C8—H8C	0.9800	C26—H26A	0.9900
C9—H9A	0.9800	C26—H26B	0.9900
C9—H9B	0.9800	C27—H27A	0.9900
C9—H9C	0.9800	C27—H27B	0.9900
C11—C12	1.4036 (14)	C28—H28A	0.9800
C11—H11	0.9500	C28—H28B	0.9800
C12—C13	1.3801 (14)	C28—H28C	0.9800
C12—H12	0.9500	C29—H29A	0.9800
C13—C14	1.3986 (14)	C29—H29B	0.9800
C13—H13	0.9500	C29—H29C	0.9800
C14—C15	1.3854 (14)
C6—O1—C5	110.13 (8)	C15—C16—H16	118.5
C27—O2—H2O	104.6 (11)	C16—C17—C18	124.68 (10)
C18—N4—C25	111.32 (9)	C16—C17—H17	117.7
C18—N4—C26	125.79 (9)	C18—C17—H17	117.7
C25—N4—C26	122.80 (8)	N4—C18—C17	122.27 (10)
N1—C1—C2	178.71 (14)	N4—C18—C19	109.07 (8)
C6—C2—C1	121.63 (10)	C17—C18—C19	128.64 (9)
C6—C2—C3	119.86 (10)	C20—C19—C18	101.24 (8)
C1—C2—C3	118.48 (9)	C20—C19—C28	110.34 (8)
N2—C3—C2	179.68 (14)	C18—C19—C28	113.67 (9)
C11—C4—C7	125.61 (10)	C20—C19—C29	110.24 (9)
C11—C4—C5	127.83 (9)	C18—C19—C29	110.21 (8)
C7—C4—C5	106.52 (8)	C28—C19—C29	110.77 (9)
O1—C5—C9	106.02 (8)	C21—C20—C25	119.45 (10)
O1—C5—C4	103.28 (7)	C21—C20—C19	131.01 (10)
C9—C5—C4	113.74 (9)	C25—C20—C19	109.53 (9)
O1—C5—C8	105.87 (8)	C20—C21—C22	118.71 (11)
C9—C5—C8	113.07 (9)	C20—C21—H21	120.6
C4—C5—C8	113.70 (9)	C22—C21—H21	120.6
O1—C6—C2	117.20 (9)	C23—C22—C21	120.74 (10)
O1—C6—C7	110.88 (8)	C23—C22—H22	119.6
C2—C6—C7	131.91 (10)	C21—C22—H22	119.6
C6—C7—C4	109.13 (9)	C22—C23—C24	121.58 (10)
C6—C7—C10	126.75 (9)	C22—C23—H23	119.2
C4—C7—C10	124.12 (9)	C24—C23—H23	119.2
C5—C8—H8A	109.5	C25—C24—C23	116.57 (11)
C5—C8—H8B	109.5	C25—C24—H24	121.7
H8A—C8—H8B	109.5	C23—C24—H24	121.7
C5—C8—H8C	109.5	C20—C25—C24	122.91 (10)
H8A—C8—H8C	109.5	C20—C25—N4	108.74 (9)
H8B—C8—H8C	109.5	C24—C25—N4	128.34 (10)
C5—C9—H9A	109.5	N4—C26—C27	112.10 (9)
C5—C9—H9B	109.5	N4—C26—H26A	109.2
H9A—C9—H9B	109.5	C27—C26—H26A	109.2
C5—C9—H9C	109.5	N4—C26—H26B	109.2
H9A—C9—H9C	109.5	C27—C26—H26B	109.2
H9B—C9—H9C	109.5	H26A—C26—H26B	107.9
N3—C10—C7	176.75 (12)	O2—C27—C26	109.27 (9)
C4—C11—C12	126.54 (10)	O2—C27—H27A	109.8
C4—C11—H11	116.7	C26—C27—H27A	109.8
C12—C11—H11	116.7	O2—C27—H27B	109.8
C13—C12—C11	123.42 (10)	C26—C27—H27B	109.8
C13—C12—H12	118.3	H27A—C27—H27B	108.3
C11—C12—H12	118.3	C19—C28—H28A	109.5
C12—C13—C14	123.30 (10)	C19—C28—H28B	109.5
C12—C13—H13	118.4	H28A—C28—H28B	109.5
C14—C13—H13	118.4	C19—C28—H28C	109.5
C15—C14—C13	124.16 (10)	H28A—C28—H28C	109.5
C15—C14—H14	117.9	H28B—C28—H28C	109.5
C13—C14—H14	117.9	C19—C29—H29A	109.5
C14—C15—C16	122.12 (10)	C19—C29—H29B	109.5
C14—C15—H15	118.9	H29A—C29—H29B	109.5
C16—C15—H15	118.9	C19—C29—H29C	109.5
C17—C16—C15	123.03 (10)	H29A—C29—H29C	109.5
C17—C16—H16	118.5	H29B—C29—H29C	109.5
C6—O1—C5—C9	120.90 (9)	C26—N4—C18—C19	178.39 (9)
C6—O1—C5—C4	1.02 (10)	C16—C17—C18—N4	176.41 (10)
C6—O1—C5—C8	−118.74 (9)	C16—C17—C18—C19	−4.91 (18)
C11—C4—C5—O1	175.76 (10)	N4—C18—C19—C20	−2.72 (11)
C7—C4—C5—O1	−2.02 (10)	C17—C18—C19—C20	178.46 (10)
C11—C4—C5—C9	61.33 (14)	N4—C18—C19—C28	−121.01 (10)
C7—C4—C5—C9	−116.45 (10)	C17—C18—C19—C28	60.16 (14)
C11—C4—C5—C8	−70.00 (14)	N4—C18—C19—C29	113.96 (10)
C7—C4—C5—C8	112.22 (10)	C17—C18—C19—C29	−64.86 (14)
C5—O1—C6—C2	−179.48 (9)	C18—C19—C20—C21	−176.50 (11)
C5—O1—C6—C7	0.39 (11)	C28—C19—C20—C21	−55.82 (15)
C1—C2—C6—O1	−174.82 (10)	C29—C19—C20—C21	66.84 (14)
C3—C2—C6—O1	3.24 (15)	C18—C19—C20—C25	2.87 (11)
C1—C2—C6—C7	5.35 (19)	C28—C19—C20—C25	123.54 (10)
C3—C2—C6—C7	−176.59 (11)	C29—C19—C20—C25	−113.79 (10)
O1—C6—C7—C4	−1.78 (12)	C25—C20—C21—C22	2.05 (16)
C2—C6—C7—C4	178.06 (11)	C19—C20—C21—C22	−178.64 (10)
O1—C6—C7—C10	178.17 (10)	C20—C21—C22—C23	−0.56 (17)
C2—C6—C7—C10	−2.00 (19)	C21—C22—C23—C24	−1.00 (18)
C11—C4—C7—C6	−175.50 (10)	C22—C23—C24—C25	0.98 (17)
C5—C4—C7—C6	2.34 (11)	C21—C20—C25—C24	−2.12 (16)
C11—C4—C7—C10	4.55 (17)	C19—C20—C25—C24	178.43 (10)
C5—C4—C7—C10	−177.60 (10)	C21—C20—C25—N4	177.37 (9)
C7—C4—C11—C12	−178.93 (10)	C19—C20—C25—N4	−2.08 (12)
C5—C4—C11—C12	3.69 (18)	C23—C24—C25—C20	0.58 (17)
C4—C11—C12—C13	−175.59 (10)	C23—C24—C25—N4	−178.81 (11)
C11—C12—C13—C14	−179.04 (10)	C18—N4—C25—C20	0.23 (12)
C12—C13—C14—C15	177.74 (10)	C26—N4—C25—C20	−176.59 (9)
C13—C14—C15—C16	−176.01 (10)	C18—N4—C25—C24	179.69 (11)
C14—C15—C16—C17	170.58 (10)	C26—N4—C25—C24	2.87 (17)
C15—C16—C17—C18	−177.05 (10)	C18—N4—C26—C27	−85.16 (12)
C25—N4—C18—C17	−179.40 (10)	C25—N4—C26—C27	91.18 (12)
C26—N4—C18—C17	−2.69 (16)	N4—C26—C27—O2	−64.57 (12)
C25—N4—C18—C19	1.69 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···N1i	0.87 (2)	2.14 (2)	2.993 (2)	166.8 (16)
C26—H26B···N2ii	0.99	2.44	3.254 (3)	139
C29—H29C···N1iii	0.98	2.72	3.670 (2)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯N1i	0.87 (2)	2.14 (2)	2.993 (2)	166.8 (16)
C26—H26B⋯N2ii	0.99	2.44	3.254 (3)	139
C29—H29C⋯N1iii	0.98	2.72	3.670 (2)	164

Symmetry codes: (i) ; (ii) ; (iii) .