2-(3-Cyano-4-{3-[1-(2-hy-droxy-eth-yl)-3,3-dimethyl-1,3-di-hydro-indol-2-yl-idene]prop-2-en-yl}-5,5-dimethyl-5H-furan-2-yl-idene)malono-nitrile.

The title compound, C25H24N4O2, adopts a cisoid configuration and has twofold orientational disorder of the 2-hy-droxy-ethyl group. The mol-ecule is twisted from planarity so that the dihedral angle between the terminating indol-2-yl-idene and the furan-2-yl-idene moiety mean planes is 12.75 (7)°. Conformational disorder occurs at the indol-2-yl-idene N atom, which results in two orientations for the hy-droxy-ethyl group [occupancy ratio = 0.896 (2):0.104 (2)], and the hy-droxy O atom of the 2-hy-droxy-ethyl group is located over three sites [occupancy ratio = 0.548 (2):0.348 (2):0.104 (2)]. An intra-molecular C-H⋯O hydrogen bond involving the lowest occupancy hy-droxy O atom is observed. In the crystal, the mol-ecules pack in parallel dimeric sheets about centres of symmetry, utilizing O-H⋯N(cyano), C-H⋯N(cyano) and O-H⋯O hydrogen bonds, in two sets parallel to (02-1) and (021) planes.

Related literature

For general background to organic non-linear optical (NLO) materials and details of similar structures, see: Kay et al. (2004 ▶); Dalton et al. (1999 ▶); Harper et al. (1999 ▶); Kay et al. (2001a ▶,b ▶); Bhuiyan et al. (2011 ▶); Gainsford et al. (2011 ▶); Ma et al. (2002 ▶); Mao et al. (1998 ▶); Smith et al. (2010 ▶); Teshome et al. (2009 ▶). For the synthesis of the title compound, see: Bhuiyan et al. (2011 ▶). For the definition of bond-length alternation (BLA), see: Marder et al. (1993 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For details of the Cambridge Structural Database (CSD), see: Allen (2002 ▶).

Experimental

Crystal data

C25H24N4O2

M = 412.48

Monoclinic,

a = 9.4276 (4) Å

b = 21.5486 (9) Å

c = 11.1178 (5) Å

β = 103.916 (2)°

V = 2192.31 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 120 K

0.65 × 0.31 × 0.13 mm

Data collection

Bruker–Nonius APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.629, T max = 0.746

50145 measured reflections

6431 independent reflections

4754 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.155

S = 1.03

6431 reflections

311 parameters

8 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.52 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL2012, PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2006 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813033242/pk2507sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813033242/pk2507Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813033242/pk2507Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

C25H24N4O2	F(000) = 872
Mr = 412.48	Dx = 1.250 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9996 reflections
a = 9.4276 (4) Å	θ = 2.4–30.0°
b = 21.5486 (9) Å	µ = 0.08 mm−1
c = 11.1178 (5) Å	T = 120 K
β = 103.916 (2)°	Block, blue
V = 2192.31 (16) Å3	0.65 × 0.31 × 0.13 mm
Z = 4

Bruker–Nonius APEXII CCD area-detector diffractometer	6431 independent reflections
Radiation source: fine-focus sealed tube	4754 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 8.333 pixels mm-1	θmax = 30.2°, θmin = 2.7°
φ and ω scans	h = −13→12
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −30→30
Tmin = 0.629, Tmax = 0.746	l = −15→15
50145 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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0688P)2 + 1.0008P] where P = (Fo2 + 2Fc2)/3
6431 reflections	(Δ/σ)max < 0.001
311 parameters	Δρmax = 0.38 e Å−3
8 restraints	Δρmin = −0.52 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	Occ. (<1)
O1	0.63766 (11)	0.63737 (5)	0.49304 (11)	0.0335 (2)
N1	0.14137 (16)	0.57222 (8)	0.39517 (18)	0.0514 (4)
N2	0.36701 (16)	0.73490 (7)	0.56984 (15)	0.0421 (3)
N3	0.34340 (16)	0.48266 (8)	0.24877 (17)	0.0518 (4)
C1	0.25102 (16)	0.59701 (7)	0.42748 (15)	0.0344 (3)
C2	0.38498 (15)	0.62889 (7)	0.46900 (14)	0.0302 (3)
C3	0.37879 (16)	0.68746 (7)	0.52649 (14)	0.0319 (3)
C4	0.68760 (15)	0.55350 (6)	0.37397 (13)	0.0273 (3)
C5	0.75963 (14)	0.60753 (7)	0.45254 (14)	0.0281 (3)
C6	0.51422 (15)	0.60667 (7)	0.44612 (13)	0.0282 (3)
C7	0.53982 (15)	0.55468 (7)	0.37537 (13)	0.0283 (3)
C8	0.81902 (17)	0.65591 (7)	0.37893 (16)	0.0361 (3)
H8A	0.7422	0.6683	0.3067	0.054*
H8B	0.9018	0.6385	0.3511	0.054*
H8C	0.8516	0.6923	0.4313	0.054*
C9	0.87158 (16)	0.58711 (7)	0.56768 (14)	0.0335 (3)
H9A	0.9087	0.6235	0.6184	0.050*
H9B	0.9527	0.5661	0.5435	0.050*
H9C	0.8258	0.5585	0.6156	0.050*
C10	0.42912 (16)	0.51515 (8)	0.30741 (15)	0.0342 (3)
C11	0.76702 (15)	0.51590 (7)	0.31209 (14)	0.0300 (3)
H11	0.8687	0.5239	0.3253	0.036*
C12	0.70918 (15)	0.46773 (7)	0.23262 (13)	0.0288 (3)
H12	0.6101	0.4564	0.2253	0.035*
C13	0.78859 (16)	0.43509 (7)	0.16310 (14)	0.0324 (3)
H13	0.8894	0.4447	0.1757	0.039*
C14	0.73222 (15)	0.38957 (7)	0.07677 (13)	0.0289 (3)
C15	0.57736 (15)	0.36373 (6)	0.03954 (13)	0.0260 (3)
C16	0.58984 (16)	0.31748 (6)	−0.05962 (13)	0.0280 (3)
C17	0.48672 (18)	0.27866 (7)	−0.13049 (15)	0.0358 (3)
H17	0.3902	0.2770	−0.1189	0.043*
C18	0.5276 (2)	0.24182 (8)	−0.21974 (16)	0.0418 (4)
H18	0.4575	0.2153	−0.2705	0.050*
C19	0.6681 (2)	0.24341 (9)	−0.23514 (16)	0.0451 (4)
H19	0.6932	0.2181	−0.2969	0.054*
C20	0.7737 (2)	0.28110 (9)	−0.16259 (16)	0.0445 (4)
H20	0.8713	0.2817	−0.1717	0.053*
C21	0.72999 (17)	0.31800 (8)	−0.07588 (14)	0.0344 (3)
C22	0.46596 (17)	0.41387 (8)	−0.01844 (16)	0.0374 (3)
H22A	0.5009	0.4360	−0.0827	0.056*
H22B	0.4543	0.4432	0.0458	0.056*
H22C	0.3717	0.3943	−0.0554	0.056*
C23	0.5323 (2)	0.33128 (8)	0.14723 (16)	0.0458 (4)
H23A	0.4404	0.3089	0.1158	0.069*
H23B	0.5190	0.3623	0.2080	0.069*
H23C	0.6087	0.3019	0.1868	0.069*
N4A	0.81429 (15)	0.35927 (7)	0.01028 (14)	0.0290 (3)	0.896 (2)
C24A	0.96803 (18)	0.37120 (9)	0.01489 (17)	0.0356 (4)	0.896 (2)
H24A	1.0180	0.3315	0.0076	0.043*	0.896 (2)
H24B	1.0155	0.3901	0.0957	0.043*	0.896 (2)
C25A	0.9838 (3)	0.41401 (13)	−0.0880 (3)	0.0596 (6)*	0.896 (2)
H25A	1.0890	0.4183	−0.0856	0.072*	0.548 (2)
H25B	0.9358	0.3946	−0.1682	0.072*	0.548 (2)
O2A1	0.9263 (3)	0.47186 (17)	−0.0833 (3)	0.0675 (9)	0.548 (2)
H211	0.844 (4)	0.469 (3)	−0.136 (5)	0.101*	0.548 (2)
O2A2	1.1107 (5)	0.4305 (2)	−0.0912 (4)	0.0596 (6)*	0.348 (2)
H212	1.139 (9)	0.447 (4)	−0.021 (4)	0.089*	0.348 (2)
H25C	0.959 (8)	0.386 (3)	−0.161 (5)	0.089*	0.348 (2)
H25D	0.905 (8)	0.444 (4)	−0.120 (10)	0.089*	0.348 (2)
N4B	0.7997 (16)	0.3841 (8)	−0.0305 (15)	0.0384 (19)*	0.104 (2)
C24B	0.9155 (19)	0.4140 (8)	−0.0540 (16)	0.0384 (19)*	0.104 (2)
H24C	0.9153	0.4570	−0.0226	0.046*	0.104 (2)
H24D	0.9011	0.4167	−0.1451	0.046*	0.104 (2)
C25B	1.0719 (17)	0.3854 (8)	0.0016 (12)	0.0384 (19)*	0.104 (2)
H25E	1.0732	0.3417	−0.0258	0.046*	0.104 (2)
H25F	1.1455	0.4086	−0.0307	0.046*	0.104 (2)
O2B	1.1083 (12)	0.3875 (5)	0.1268 (10)	0.0384 (19)*	0.104 (2)
H2B	1.0676	0.4182	0.1509	0.058*	0.104 (2)

	U11	U22	U33	U12	U13	U23
O1	0.0254 (5)	0.0339 (5)	0.0413 (6)	0.0018 (4)	0.0080 (4)	−0.0115 (5)
N1	0.0296 (7)	0.0499 (9)	0.0738 (11)	0.0026 (6)	0.0107 (7)	−0.0096 (8)
N2	0.0428 (8)	0.0404 (8)	0.0472 (8)	0.0028 (6)	0.0186 (6)	−0.0045 (6)
N3	0.0327 (7)	0.0672 (11)	0.0592 (10)	−0.0116 (7)	0.0184 (7)	−0.0276 (8)
C1	0.0285 (7)	0.0352 (8)	0.0401 (8)	0.0078 (6)	0.0094 (6)	−0.0005 (6)
C2	0.0278 (7)	0.0325 (7)	0.0312 (7)	0.0042 (5)	0.0086 (5)	−0.0001 (6)
C3	0.0293 (7)	0.0372 (8)	0.0315 (7)	0.0037 (6)	0.0119 (6)	0.0022 (6)
C4	0.0252 (6)	0.0279 (6)	0.0273 (7)	0.0021 (5)	0.0032 (5)	−0.0018 (5)
C5	0.0221 (6)	0.0286 (7)	0.0334 (7)	0.0027 (5)	0.0063 (5)	−0.0055 (5)
C6	0.0261 (6)	0.0304 (7)	0.0276 (7)	0.0025 (5)	0.0053 (5)	0.0002 (5)
C7	0.0249 (6)	0.0304 (7)	0.0289 (7)	0.0016 (5)	0.0051 (5)	−0.0024 (5)
C8	0.0343 (7)	0.0324 (7)	0.0415 (9)	0.0020 (6)	0.0090 (6)	0.0018 (6)
C9	0.0301 (7)	0.0350 (8)	0.0326 (7)	0.0008 (6)	0.0020 (6)	−0.0045 (6)
C10	0.0265 (7)	0.0414 (8)	0.0368 (8)	−0.0010 (6)	0.0114 (6)	−0.0074 (7)
C11	0.0236 (6)	0.0328 (7)	0.0325 (7)	0.0026 (5)	0.0046 (5)	−0.0055 (6)
C12	0.0254 (6)	0.0308 (7)	0.0294 (7)	0.0027 (5)	0.0050 (5)	−0.0037 (5)
C13	0.0250 (6)	0.0367 (8)	0.0357 (8)	0.0010 (5)	0.0077 (5)	−0.0079 (6)
C14	0.0273 (6)	0.0324 (7)	0.0276 (7)	0.0044 (5)	0.0077 (5)	−0.0021 (5)
C15	0.0285 (6)	0.0254 (6)	0.0245 (6)	0.0022 (5)	0.0072 (5)	0.0017 (5)
C16	0.0342 (7)	0.0250 (6)	0.0238 (6)	0.0051 (5)	0.0050 (5)	0.0021 (5)
C17	0.0409 (8)	0.0308 (7)	0.0334 (8)	0.0008 (6)	0.0046 (6)	−0.0004 (6)
C18	0.0541 (10)	0.0329 (8)	0.0327 (8)	0.0037 (7)	−0.0003 (7)	−0.0061 (6)
C19	0.0556 (10)	0.0445 (9)	0.0315 (8)	0.0129 (8)	0.0034 (7)	−0.0115 (7)
C20	0.0431 (9)	0.0535 (10)	0.0363 (9)	0.0114 (8)	0.0088 (7)	−0.0128 (8)
C21	0.0357 (7)	0.0380 (8)	0.0284 (7)	0.0066 (6)	0.0059 (6)	−0.0054 (6)
C22	0.0326 (7)	0.0357 (8)	0.0395 (8)	0.0093 (6)	0.0003 (6)	−0.0047 (7)
C23	0.0701 (12)	0.0383 (9)	0.0351 (9)	−0.0105 (8)	0.0246 (8)	−0.0007 (7)
N4A	0.0284 (7)	0.0327 (7)	0.0270 (7)	0.0038 (5)	0.0088 (5)	−0.0032 (6)
C24A	0.0288 (8)	0.0422 (9)	0.0379 (9)	0.0061 (7)	0.0121 (7)	−0.0006 (7)
O2A1	0.0470 (15)	0.081 (2)	0.069 (2)	−0.0066 (14)	0.0018 (13)	0.0281 (17)

O1—C6	1.3312 (17)	C16—C17	1.377 (2)
O1—C5	1.4790 (16)	C17—C18	1.395 (2)
N1—C1	1.142 (2)	C17—H17	0.9500
N2—C3	1.147 (2)	C18—C19	1.377 (3)
N3—C10	1.147 (2)	C18—H18	0.9500
C1—C2	1.414 (2)	C19—C20	1.384 (3)
C2—C6	1.3883 (19)	C19—H19	0.9500
C2—C3	1.422 (2)	C20—C21	1.386 (2)
C4—C11	1.3922 (19)	C20—H20	0.9500
C4—C7	1.3972 (19)	C21—N4A	1.405 (2)
C4—C5	1.5148 (19)	C21—N4B	1.599 (16)
C5—C8	1.513 (2)	C22—H22A	0.9800
C5—C9	1.515 (2)	C22—H22B	0.9800
C6—C7	1.423 (2)	C22—H22C	0.9800
C7—C10	1.416 (2)	C23—H23A	0.9800
C8—H8A	0.9800	C23—H23B	0.9800
C8—H8B	0.9800	C23—H23C	0.9800
C8—H8C	0.9800	N4A—C24A	1.461 (2)
C9—H9A	0.9800	C24A—C25A	1.504 (3)
C9—H9B	0.9800	C24A—H24A	0.9900
C9—H9C	0.9800	C24A—H24B	0.9900
C11—C12	1.387 (2)	C25A—O2A1	1.365 (4)
C11—H11	0.9500	C25A—H25A	0.9900
C12—C13	1.389 (2)	C25A—H25B	0.9900
C12—H12	0.9500	O2A1—H211	0.85 (3)
C13—C14	1.386 (2)	O2A2—H212	0.84 (3)
C13—H13	0.9500	N4B—C24B	1.35 (2)
C14—N4A	1.3588 (19)	C24B—C25B	1.58 (2)
C14—N4B	1.485 (16)	C24B—H24C	0.9900
C14—C15	1.524 (2)	C24B—H24D	0.9900
C15—C16	1.5116 (19)	C25B—O2B	1.352 (13)
C15—C23	1.532 (2)	C25B—H25E	0.9900
C15—C22	1.536 (2)	C25B—H25F	0.9900
C16—C21	1.376 (2)	O2B—H2B	0.8400
C6—O1—C5	109.57 (11)	C18—C17—H17	120.8
N1—C1—C2	178.50 (18)	C19—C18—C17	120.84 (16)
C6—C2—C1	121.79 (14)	C19—C18—H18	119.6
C6—C2—C3	121.41 (14)	C17—C18—H18	119.6
C1—C2—C3	116.61 (13)	C18—C19—C20	121.40 (16)
N2—C3—C2	176.76 (17)	C18—C19—H19	119.3
C11—C4—C7	132.24 (13)	C20—C19—H19	119.3
C11—C4—C5	120.83 (12)	C19—C20—C21	116.72 (16)
C7—C4—C5	106.83 (12)	C19—C20—H20	121.6
O1—C5—C8	106.32 (11)	C21—C20—H20	121.6
O1—C5—C4	103.66 (10)	C16—C21—C20	122.82 (15)
C8—C5—C4	112.99 (13)	C16—C21—N4A	108.60 (13)
O1—C5—C9	107.67 (12)	C20—C21—N4A	128.55 (15)
C8—C5—C9	112.56 (12)	C16—C21—N4B	107.5 (6)
C4—C5—C9	112.85 (12)	C20—C21—N4B	124.2 (6)
O1—C6—C2	118.67 (13)	C15—C22—H22A	109.5
O1—C6—C7	111.07 (12)	C15—C22—H22B	109.5
C2—C6—C7	130.24 (14)	H22A—C22—H22B	109.5
C4—C7—C10	126.29 (13)	C15—C22—H22C	109.5
C4—C7—C6	108.83 (12)	H22A—C22—H22C	109.5
C10—C7—C6	124.56 (13)	H22B—C22—H22C	109.5
C5—C8—H8A	109.5	C15—C23—H23A	109.5
C5—C8—H8B	109.5	C15—C23—H23B	109.5
H8A—C8—H8B	109.5	H23A—C23—H23B	109.5
C5—C8—H8C	109.5	C15—C23—H23C	109.5
H8A—C8—H8C	109.5	H23A—C23—H23C	109.5
H8B—C8—H8C	109.5	H23B—C23—H23C	109.5
C5—C9—H9A	109.5	C14—N4A—C21	111.86 (13)
C5—C9—H9B	109.5	C14—N4A—C24A	125.91 (14)
H9A—C9—H9B	109.5	C21—N4A—C24A	121.93 (13)
C5—C9—H9C	109.5	N4A—C24A—C25A	111.10 (17)
H9A—C9—H9C	109.5	N4A—C24A—H24A	109.4
H9B—C9—H9C	109.5	C25A—C24A—H24A	109.4
N3—C10—C7	176.92 (17)	N4A—C24A—H24B	109.4
C12—C11—C4	125.07 (13)	C25A—C24A—H24B	109.4
C12—C11—H11	117.5	H24A—C24A—H24B	108.0
C4—C11—H11	117.5	O2A1—C25A—C24A	114.7 (2)
C11—C12—C13	123.45 (13)	O2A1—C25A—H25A	108.6
C11—C12—H12	118.3	C24A—C25A—H25A	108.6
C13—C12—H12	118.3	O2A1—C25A—H25B	108.6
C14—C13—C12	125.12 (13)	C24A—C25A—H25B	108.6
C14—C13—H13	117.4	H25A—C25A—H25B	107.6
C12—C13—H13	117.4	C25A—O2A1—H211	103 (5)
N4A—C14—C13	122.90 (13)	C24B—N4B—C14	130.0 (13)
C13—C14—N4B	116.4 (6)	C24B—N4B—C21	131.0 (13)
N4A—C14—C15	108.08 (12)	C14—N4B—C21	95.8 (9)
C13—C14—C15	129.02 (13)	N4B—C24B—C25B	117.4 (15)
N4B—C14—C15	108.7 (6)	N4B—C24B—H24C	107.9
C16—C15—C14	101.62 (11)	C25B—C24B—H24C	107.9
C16—C15—C23	110.73 (12)	N4B—C24B—H24D	107.9
C14—C15—C23	112.45 (13)	C25B—C24B—H24D	107.9
C16—C15—C22	108.84 (12)	H24C—C24B—H24D	107.2
C14—C15—C22	111.76 (12)	O2B—C25B—C24B	111.8 (13)
C23—C15—C22	111.03 (13)	O2B—C25B—H25E	109.3
C21—C16—C17	119.85 (14)	C24B—C25B—H25E	109.3
C21—C16—C15	109.64 (13)	O2B—C25B—H25F	109.3
C17—C16—C15	130.50 (14)	C24B—C25B—H25F	109.3
C16—C17—C18	118.35 (16)	H25E—C25B—H25F	107.9
C16—C17—H17	120.8	C25B—O2B—H2B	109.5
C6—O1—C5—C8	119.01 (13)	C21—C16—C17—C18	−1.6 (2)
C6—O1—C5—C4	−0.33 (15)	C15—C16—C17—C18	177.65 (14)
C6—O1—C5—C9	−120.13 (13)	C16—C17—C18—C19	1.1 (2)
C11—C4—C5—O1	175.98 (13)	C17—C18—C19—C20	0.4 (3)
C7—C4—C5—O1	−0.88 (15)	C18—C19—C20—C21	−1.4 (3)
C11—C4—C5—C8	61.32 (18)	C17—C16—C21—C20	0.6 (2)
C7—C4—C5—C8	−115.54 (13)	C15—C16—C21—C20	−178.78 (15)
C11—C4—C5—C9	−67.82 (18)	C17—C16—C21—N4A	−177.63 (14)
C7—C4—C5—C9	115.32 (13)	C15—C16—C21—N4A	2.97 (17)
C5—O1—C6—C2	−177.33 (13)	C17—C16—C21—N4B	155.4 (6)
C5—O1—C6—C7	1.43 (16)	C15—C16—C21—N4B	−24.0 (7)
C1—C2—C6—O1	−176.75 (14)	C19—C20—C21—C16	0.9 (3)
C3—C2—C6—O1	8.5 (2)	C19—C20—C21—N4A	178.75 (17)
C1—C2—C6—C7	4.8 (3)	C19—C20—C21—N4B	−149.7 (7)
C3—C2—C6—C7	−169.99 (15)	C13—C14—N4A—C21	−176.54 (15)
C11—C4—C7—C10	−0.9 (3)	N4B—C14—N4A—C21	−91.8 (13)
C5—C4—C7—C10	175.45 (15)	C15—C14—N4A—C21	4.19 (18)
C11—C4—C7—C6	−174.63 (16)	C13—C14—N4A—C24A	−2.7 (3)
C5—C4—C7—C6	1.72 (16)	N4B—C14—N4A—C24A	82.0 (13)
O1—C6—C7—C4	−2.04 (17)	C15—C14—N4A—C24A	177.99 (15)
C2—C6—C7—C4	176.53 (15)	C16—C21—N4A—C14	−4.59 (19)
O1—C6—C7—C10	−175.90 (14)	C20—C21—N4A—C14	177.29 (17)
C2—C6—C7—C10	2.7 (3)	N4B—C21—N4A—C14	87.2 (13)
C7—C4—C11—C12	−0.2 (3)	C16—C21—N4A—C24A	−178.68 (15)
C5—C4—C11—C12	−176.12 (14)	C20—C21—N4A—C24A	3.2 (3)
C4—C11—C12—C13	173.48 (15)	N4B—C21—N4A—C24A	−86.9 (13)
C11—C12—C13—C14	−175.49 (15)	C14—N4A—C24A—C25A	−96.2 (2)
C12—C13—C14—N4A	179.46 (16)	C21—N4A—C24A—C25A	77.1 (2)
C12—C13—C14—N4B	148.2 (7)	N4A—C24A—C25A—O2A1	62.7 (3)
C12—C13—C14—C15	−1.4 (3)	N4A—C14—N4B—C24B	−106 (2)
N4A—C14—C15—C16	−2.18 (15)	C13—C14—N4B—C24B	5 (2)
C13—C14—C15—C16	178.62 (15)	C15—C14—N4B—C24B	160.6 (16)
N4B—C14—C15—C16	27.1 (7)	N4A—C14—N4B—C21	55.0 (10)
N4A—C14—C15—C23	116.24 (15)	C13—C14—N4B—C21	166.0 (4)
C13—C14—C15—C23	−63.0 (2)	C15—C14—N4B—C21	−38.5 (9)
N4B—C14—C15—C23	145.5 (7)	C16—C21—N4B—C24B	−161.1 (16)
N4A—C14—C15—C22	−118.10 (14)	C20—C21—N4B—C24B	−7 (2)
C13—C14—C15—C22	62.7 (2)	N4A—C21—N4B—C24B	102 (2)
N4B—C14—C15—C22	−88.8 (7)	C16—C21—N4B—C14	38.2 (9)
C14—C15—C16—C21	−0.53 (15)	C20—C21—N4B—C14	−167.5 (3)
C23—C15—C16—C21	−120.18 (15)	N4A—C21—N4B—C14	−58.5 (10)
C22—C15—C16—C21	117.51 (14)	C14—N4B—C24B—C25B	87 (2)
C14—C15—C16—C17	−179.84 (15)	C21—N4B—C24B—C25B	−68 (2)
C23—C15—C16—C17	60.5 (2)	N4B—C24B—C25B—O2B	−65.8 (19)
C22—C15—C16—C17	−61.81 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O2A1—H211···N3i	0.85 (3)	2.17 (4)	2.925 (3)	148 (6)
O2A2—H212···O2A1ii	0.84	2.27	2.939 (4)	137
C8—H8B···N1iii	0.98	2.62	3.501 (2)	150
C9—H9C···N3iv	0.98	2.60	3.539 (2)	160
C13—H13···O2B	0.95	2.57	3.299 (11)	134
C20—H20···N2v	0.95	2.65	3.442 (2)	141
C24A—H24A···N2v	0.99	2.59	3.555 (2)	166
C25A—H25B···N1i	0.99	2.55	3.348 (3)	137
C25B—H25E···N2v	0.99	2.45	3.420 (17)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2A1—H211⋯N3i	0.85 (3)	2.17 (4)	2.925 (3)	148 (6)
O2A2—H212⋯O2A1ii	0.84	2.27	2.939 (4)	137
C8—H8B⋯N1iii	0.98	2.62	3.501 (2)	150
C9—H9C⋯N3iv	0.98	2.60	3.539 (2)	160
C13—H13⋯O2B	0.95	2.57	3.299 (11)	134
C20—H20⋯N2v	0.95	2.65	3.442 (2)	141
C24A—H24A⋯N2v	0.99	2.59	3.555 (2)	166
C25A—H25B⋯N1i	0.99	2.55	3.348 (3)	137
C25B—H25E⋯N2v	0.99	2.45	3.420 (17)	167

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