2-Amino-6-[(2,6-dichloro-phen-yl)imino]-3-oxocyclo-hexa-1,4-dienecarbaldehyde.

The title compound, C(13)H(8)Cl(2)N(2)O(2), was obtained by the oxidation of diclofenac {systematic name: 2-[2-(2,6-dichloro-phenyl-amino)-phen-yl]acetic acid}, an anti-inflammatory drug, with hydrogen peroxide catalysed by chlorido[5,10,15,20-tetra-kis-(2,6-dichloro-phen-yl)porphyrinato]manganese(III), using ammonium acetate as co-catalyst. The asymmetric unit contains two crystallographically independent mol-ecules of the title compound (Z' = 2). The close packing of individual mol-ecules is mediated by a series of strong and rather directional N-H⋯Cl and N-H⋯O hydrogen bonds, plus weak π-π [distance between the individual double bonds of symmetry-related imino-quinone rings = 3.7604 (13) Å] and Cl⋯O inter-actions [3.0287 (18) Å].

Related literature

For background to diclofenac oxidation reactions using metalloporphyrins as catalysts, see: Othman et al. (2000 ▶). For oxidation of other drugs and other organic compounds by hydrogen peroxide catalysed by metalloporphyrins, see: Othman et al. (2000 ▶); Bernadou & Meunier (2004 ▶); Mansuy (2007 ▶); Neves et al. (2011 ▶); Simões et al. (2009 ▶); Rebelo et al. (2004a ▶,b ▶, 2005 ▶). For crystallographic studies from our research group of compounds with biological activity, see: Fernandes et al. (2010 ▶, 2011 ▶); Loughzail et al. (2011 ▶). For a description of the graph-set notation, see: Grell et al. (1999 ▶).

Experimental

Crystal data

C13H8Cl2N2O2

M = 295.11

Monoclinic,

a = 17.1738 (14) Å

b = 10.5718 (8) Å

c = 14.1457 (11) Å

β = 101.192 (5)°

V = 2519.4 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.51 mm−1

T = 150 K

0.07 × 0.04 × 0.01 mm

Data collection

Bruker X8 KappaCCD APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.965, T max = 0.995

24324 measured reflections

4600 independent reflections

3466 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.085

S = 1.02

4600 reflections

355 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT-Plus (Bruker, 2005 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811042619/tk2799sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042619/tk2799Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811042619/tk2799Isup3.cml

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

C13H8Cl2N2O2	F(000) = 1200
Mr = 295.11	Dx = 1.556 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5810 reflections
a = 17.1738 (14) Å	θ = 2.4–25.3°
b = 10.5718 (8) Å	µ = 0.51 mm−1
c = 14.1457 (11) Å	T = 150 K
β = 101.192 (5)°	Plate, red
V = 2519.4 (3) Å3	0.07 × 0.04 × 0.01 mm
Z = 8

Bruker X8 KappaCCD APEXII diffractometer	4600 independent reflections
Radiation source: fine-focus sealed tube	3466 reflections with I > 2σ(I)
graphite	Rint = 0.040
ω and φ scans	θmax = 25.4°, θmin = 3.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −20→20
Tmin = 0.965, Tmax = 0.995	k = −12→11
24324 measured reflections	l = −16→17

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0396P)2 + 1.1952P] where P = (Fo2 + 2Fc2)/3
4600 reflections	(Δ/σ)max = 0.001
355 parameters	Δρmax = 0.24 e Å−3
6 restraints	Δρmin = −0.24 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
Cl1	0.49916 (4)	0.47039 (5)	0.65986 (4)	0.03327 (15)
Cl2	0.26299 (4)	0.18196 (7)	0.74680 (4)	0.04150 (17)
Cl3	−0.05691 (3)	0.62367 (6)	0.53847 (4)	0.03368 (16)
Cl4	0.12169 (4)	0.98217 (6)	0.40871 (5)	0.04362 (18)
O1	0.58372 (8)	0.22644 (14)	1.02574 (10)	0.0271 (3)
O2	0.36779 (9)	0.51109 (15)	1.11813 (10)	0.0308 (4)
O3	0.13914 (10)	0.96716 (17)	0.83068 (11)	0.0381 (4)
O4	0.36096 (9)	0.70522 (15)	0.73428 (10)	0.0317 (4)
N1	0.42445 (10)	0.31116 (17)	0.78706 (12)	0.0254 (4)
N2	0.49446 (10)	0.36348 (17)	1.12812 (12)	0.0234 (4)
H2X	0.4811 (12)	0.396 (2)	1.1829 (11)	0.035*
H2Y	0.5399 (9)	0.3149 (19)	1.1359 (14)	0.035*
N3	0.06269 (10)	0.83177 (18)	0.56257 (12)	0.0282 (4)
N4	0.27682 (11)	0.84936 (19)	0.83330 (12)	0.0294 (4)
H4X	0.3282 (7)	0.826 (2)	0.8623 (15)	0.044*
H4Y	0.2502 (11)	0.900 (2)	0.8693 (14)	0.044*
C1	0.37540 (13)	0.3337 (2)	0.69673 (14)	0.0246 (5)
C2	0.40534 (13)	0.4033 (2)	0.62735 (15)	0.0264 (5)
C3	0.36328 (15)	0.4175 (2)	0.53380 (15)	0.0324 (6)
H3	0.3847	0.4657	0.4883	0.039*
C4	0.28988 (15)	0.3606 (2)	0.50764 (15)	0.0351 (6)
H4	0.2604	0.3707	0.4439	0.042*
C5	0.25886 (14)	0.2893 (2)	0.57318 (16)	0.0340 (6)
H5	0.2086	0.2496	0.5547	0.041*
C6	0.30200 (13)	0.2760 (2)	0.66665 (15)	0.0293 (5)
C7	0.41077 (12)	0.36167 (19)	0.86545 (14)	0.0208 (4)
C8	0.46514 (12)	0.33341 (19)	0.95584 (14)	0.0189 (4)
C9	0.45032 (12)	0.38251 (19)	1.04179 (14)	0.0205 (4)
C10	0.37993 (12)	0.4683 (2)	1.04199 (15)	0.0234 (5)
C11	0.33030 (13)	0.4983 (2)	0.94897 (15)	0.0266 (5)
H11	0.2869	0.5547	0.9464	0.032*
C12	0.34440 (12)	0.4484 (2)	0.86732 (15)	0.0241 (5)
H12	0.3103	0.4699	0.8083	0.029*
C13	0.53477 (12)	0.25818 (19)	0.95380 (15)	0.0223 (5)
H13	0.5436	0.2311	0.8927	0.027*
C14	0.03131 (12)	0.7975 (2)	0.46603 (14)	0.0260 (5)
C15	−0.02731 (13)	0.7046 (2)	0.44466 (14)	0.0273 (5)
C16	−0.06283 (14)	0.6751 (2)	0.35062 (15)	0.0312 (5)
H16	−0.1021	0.6107	0.3381	0.037*
C17	−0.04074 (14)	0.7399 (2)	0.27537 (15)	0.0340 (6)
H17	−0.0651	0.7203	0.2109	0.041*
C18	0.01639 (14)	0.8329 (2)	0.29324 (15)	0.0322 (6)
H18	0.0317	0.8772	0.2413	0.039*
C19	0.05143 (13)	0.8613 (2)	0.38746 (16)	0.0295 (5)
C20	0.13475 (12)	0.8026 (2)	0.60230 (14)	0.0228 (5)
C21	0.16673 (12)	0.8469 (2)	0.69960 (14)	0.0224 (5)
C22	0.24313 (12)	0.8152 (2)	0.74440 (14)	0.0228 (5)
C23	0.29463 (13)	0.7359 (2)	0.69351 (15)	0.0253 (5)
C24	0.26042 (14)	0.6948 (2)	0.59531 (15)	0.0317 (5)
H24	0.2919	0.6462	0.5605	0.038*
C25	0.18613 (13)	0.7242 (2)	0.55375 (15)	0.0286 (5)
H25	0.1656	0.6936	0.4907	0.034*
C26	0.11859 (13)	0.9265 (2)	0.74825 (16)	0.0299 (5)
H26	0.0673	0.9490	0.7140	0.036*

	U11	U22	U33	U12	U13	U23
Cl1	0.0426 (3)	0.0302 (3)	0.0295 (3)	0.0019 (3)	0.0133 (3)	−0.0011 (2)
Cl2	0.0421 (4)	0.0542 (4)	0.0276 (3)	−0.0097 (3)	0.0050 (3)	0.0044 (3)
Cl3	0.0358 (3)	0.0457 (4)	0.0196 (3)	−0.0011 (3)	0.0053 (2)	0.0034 (2)
Cl4	0.0342 (3)	0.0497 (4)	0.0439 (4)	−0.0070 (3)	−0.0002 (3)	0.0110 (3)
O1	0.0270 (8)	0.0292 (8)	0.0224 (8)	0.0023 (7)	−0.0018 (7)	0.0026 (7)
O2	0.0319 (9)	0.0377 (9)	0.0247 (8)	0.0008 (7)	0.0101 (7)	−0.0064 (7)
O3	0.0365 (9)	0.0512 (11)	0.0256 (8)	0.0079 (8)	0.0039 (7)	−0.0143 (8)
O4	0.0248 (8)	0.0420 (10)	0.0261 (8)	0.0089 (7)	−0.0003 (7)	0.0023 (7)
N1	0.0298 (10)	0.0297 (10)	0.0165 (9)	0.0040 (8)	0.0036 (8)	0.0028 (8)
N2	0.0255 (10)	0.0270 (10)	0.0174 (9)	−0.0026 (8)	0.0036 (8)	−0.0011 (8)
N3	0.0258 (10)	0.0383 (11)	0.0189 (9)	0.0050 (9)	0.0008 (8)	−0.0034 (8)
N4	0.0281 (10)	0.0381 (12)	0.0190 (9)	0.0055 (9)	−0.0028 (8)	−0.0049 (8)
C1	0.0306 (12)	0.0250 (12)	0.0173 (10)	0.0116 (10)	0.0023 (9)	0.0003 (9)
C2	0.0377 (13)	0.0222 (12)	0.0207 (10)	0.0101 (10)	0.0087 (9)	−0.0006 (9)
C3	0.0524 (16)	0.0274 (13)	0.0182 (11)	0.0140 (12)	0.0093 (10)	0.0022 (10)
C4	0.0501 (16)	0.0367 (14)	0.0155 (10)	0.0157 (12)	−0.0014 (10)	−0.0010 (10)
C5	0.0338 (13)	0.0406 (14)	0.0250 (12)	0.0088 (11)	−0.0007 (10)	−0.0064 (11)
C6	0.0341 (13)	0.0324 (13)	0.0209 (11)	0.0082 (11)	0.0038 (10)	0.0028 (10)
C7	0.0212 (11)	0.0206 (11)	0.0205 (10)	−0.0022 (9)	0.0040 (9)	0.0032 (9)
C8	0.0204 (10)	0.0177 (10)	0.0182 (10)	−0.0027 (8)	0.0027 (8)	0.0023 (8)
C9	0.0209 (10)	0.0197 (11)	0.0206 (10)	−0.0065 (9)	0.0032 (9)	0.0026 (9)
C10	0.0230 (11)	0.0233 (11)	0.0248 (11)	−0.0064 (9)	0.0067 (9)	−0.0017 (9)
C11	0.0230 (11)	0.0273 (12)	0.0288 (11)	0.0018 (10)	0.0033 (9)	0.0004 (10)
C12	0.0246 (11)	0.0236 (11)	0.0224 (11)	0.0023 (9)	0.0002 (9)	0.0019 (9)
C13	0.0261 (11)	0.0194 (11)	0.0212 (10)	−0.0030 (9)	0.0041 (9)	0.0000 (9)
C14	0.0220 (11)	0.0367 (13)	0.0186 (10)	0.0096 (10)	0.0018 (9)	−0.0012 (10)
C15	0.0266 (12)	0.0361 (13)	0.0188 (10)	0.0048 (10)	0.0036 (9)	0.0015 (10)
C16	0.0308 (13)	0.0394 (14)	0.0221 (11)	0.0013 (11)	0.0016 (10)	−0.0003 (10)
C17	0.0362 (13)	0.0468 (15)	0.0164 (10)	0.0046 (12)	−0.0011 (10)	−0.0023 (10)
C18	0.0332 (13)	0.0421 (14)	0.0210 (11)	0.0095 (11)	0.0046 (10)	0.0074 (10)
C19	0.0220 (11)	0.0357 (13)	0.0298 (12)	0.0043 (10)	0.0029 (9)	0.0028 (10)
C20	0.0233 (11)	0.0257 (12)	0.0193 (10)	0.0016 (9)	0.0035 (9)	0.0024 (9)
C21	0.0239 (11)	0.0247 (12)	0.0189 (10)	0.0009 (9)	0.0046 (9)	−0.0011 (9)
C22	0.0229 (11)	0.0256 (11)	0.0194 (10)	−0.0007 (9)	0.0031 (9)	0.0008 (9)
C23	0.0245 (12)	0.0289 (12)	0.0219 (10)	0.0032 (10)	0.0029 (9)	0.0029 (9)
C24	0.0323 (13)	0.0386 (14)	0.0234 (11)	0.0126 (11)	0.0032 (10)	−0.0069 (10)
C25	0.0321 (12)	0.0335 (13)	0.0188 (10)	0.0060 (10)	0.0015 (9)	−0.0054 (10)
C26	0.0245 (12)	0.0380 (14)	0.0265 (12)	0.0036 (10)	0.0030 (9)	−0.0023 (11)

Cl1—C2	1.738 (2)	C7—C12	1.467 (3)
Cl2—C6	1.737 (2)	C8—C9	1.390 (3)
Cl3—C15	1.736 (2)	C8—C13	1.441 (3)
Cl4—C19	1.743 (2)	C9—C10	1.512 (3)
O1—C13	1.234 (2)	C10—C11	1.457 (3)
O2—C10	1.223 (2)	C11—C12	1.334 (3)
O3—C26	1.229 (3)	C11—H11	0.9500
O4—C23	1.217 (2)	C12—H12	0.9500
N1—C7	1.293 (3)	C13—H13	0.9500
N1—C1	1.408 (3)	C14—C15	1.397 (3)
N2—C9	1.322 (2)	C14—C19	1.400 (3)
N2—H2X	0.917 (9)	C15—C16	1.387 (3)
N2—H2Y	0.922 (9)	C16—C17	1.380 (3)
N3—C20	1.293 (3)	C16—H16	0.9500
N3—C14	1.414 (3)	C17—C18	1.377 (3)
N4—C22	1.328 (3)	C17—H17	0.9500
N4—H4X	0.931 (9)	C18—C19	1.385 (3)
N4—H4Y	0.921 (9)	C18—H18	0.9500
C1—C6	1.390 (3)	C20—C21	1.456 (3)
C1—C2	1.402 (3)	C20—C25	1.474 (3)
C2—C3	1.387 (3)	C21—C22	1.383 (3)
C3—C4	1.381 (3)	C21—C26	1.444 (3)
C3—H3	0.9500	C22—C23	1.501 (3)
C4—C5	1.380 (3)	C23—C24	1.465 (3)
C4—H4	0.9500	C24—C25	1.334 (3)
C5—C6	1.392 (3)	C24—H24	0.9500
C5—H5	0.9500	C25—H25	0.9500
C7—C8	1.460 (3)	C26—H26	0.9500
C7—N1—C1	122.17 (18)	C7—C12—H12	118.8
C9—N2—H2X	122.1 (13)	O1—C13—C8	124.65 (19)
C9—N2—H2Y	121.0 (13)	O1—C13—H13	117.7
H2X—N2—H2Y	116.9 (14)	C8—C13—H13	117.7
C20—N3—C14	120.77 (18)	C15—C14—C19	116.48 (19)
C22—N4—H4X	123.3 (13)	C15—C14—N3	120.83 (19)
C22—N4—H4Y	120.7 (13)	C19—C14—N3	122.5 (2)
H4X—N4—H4Y	116.0 (14)	C16—C15—C14	122.0 (2)
C6—C1—C2	116.73 (19)	C16—C15—Cl3	118.86 (18)
C6—C1—N1	123.4 (2)	C14—C15—Cl3	119.13 (16)
C2—C1—N1	119.2 (2)	C17—C16—C15	119.5 (2)
C3—C2—C1	122.0 (2)	C17—C16—H16	120.2
C3—C2—Cl1	119.52 (18)	C15—C16—H16	120.2
C1—C2—Cl1	118.43 (16)	C18—C17—C16	120.4 (2)
C4—C3—C2	119.2 (2)	C18—C17—H17	119.8
C4—C3—H3	120.4	C16—C17—H17	119.8
C2—C3—H3	120.4	C17—C18—C19	119.5 (2)
C5—C4—C3	120.6 (2)	C17—C18—H18	120.2
C5—C4—H4	119.7	C19—C18—H18	120.2
C3—C4—H4	119.7	C18—C19—C14	122.1 (2)
C4—C5—C6	119.3 (2)	C18—C19—Cl4	118.83 (18)
C4—C5—H5	120.3	C14—C19—Cl4	119.07 (17)
C6—C5—H5	120.3	N3—C20—C21	119.18 (19)
C1—C6—C5	122.1 (2)	N3—C20—C25	122.72 (19)
C1—C6—Cl2	119.52 (16)	C21—C20—C25	118.09 (18)
C5—C6—Cl2	118.42 (19)	C22—C21—C26	120.17 (19)
N1—C7—C8	118.35 (18)	C22—C21—C20	120.36 (19)
N1—C7—C12	123.02 (19)	C26—C21—C20	119.46 (18)
C8—C7—C12	118.62 (18)	N4—C22—C21	124.6 (2)
C9—C8—C13	121.14 (18)	N4—C22—C23	114.66 (18)
C9—C8—C7	119.67 (18)	C21—C22—C23	120.70 (18)
C13—C8—C7	119.16 (17)	O4—C23—C24	122.5 (2)
N2—C9—C8	125.56 (19)	O4—C23—C22	120.41 (19)
N2—C9—C10	113.89 (18)	C24—C23—C22	117.07 (18)
C8—C9—C10	120.53 (18)	C25—C24—C23	121.5 (2)
O2—C10—C11	123.0 (2)	C25—C24—H24	119.3
O2—C10—C9	119.78 (19)	C23—C24—H24	119.3
C11—C10—C9	117.17 (18)	C24—C25—C20	122.3 (2)
C12—C11—C10	121.5 (2)	C24—C25—H25	118.9
C12—C11—H11	119.2	C20—C25—H25	118.9
C10—C11—H11	119.2	O3—C26—C21	124.8 (2)
C11—C12—C7	122.34 (19)	O3—C26—H26	117.6
C11—C12—H12	118.8	C21—C26—H26	117.6
C7—N1—C1—C6	−77.3 (3)	C20—N3—C14—C15	110.1 (2)
C7—N1—C1—C2	111.9 (2)	C20—N3—C14—C19	−75.8 (3)
C6—C1—C2—C3	1.7 (3)	C19—C14—C15—C16	1.2 (3)
N1—C1—C2—C3	173.0 (2)	N3—C14—C15—C16	175.7 (2)
C6—C1—C2—Cl1	−176.76 (16)	C19—C14—C15—Cl3	−178.67 (16)
N1—C1—C2—Cl1	−5.4 (3)	N3—C14—C15—Cl3	−4.2 (3)
C1—C2—C3—C4	−0.4 (3)	C14—C15—C16—C17	−0.8 (3)
Cl1—C2—C3—C4	177.98 (17)	Cl3—C15—C16—C17	179.07 (18)
C2—C3—C4—C5	−0.8 (3)	C15—C16—C17—C18	0.3 (4)
C3—C4—C5—C6	0.7 (3)	C16—C17—C18—C19	−0.2 (3)
C2—C1—C6—C5	−1.8 (3)	C17—C18—C19—C14	0.7 (3)
N1—C1—C6—C5	−172.7 (2)	C17—C18—C19—Cl4	−178.31 (18)
C2—C1—C6—Cl2	177.02 (16)	C15—C14—C19—C18	−1.1 (3)
N1—C1—C6—Cl2	6.1 (3)	N3—C14—C19—C18	−175.5 (2)
C4—C5—C6—C1	0.7 (3)	C15—C14—C19—Cl4	177.85 (17)
C4—C5—C6—Cl2	−178.15 (17)	N3—C14—C19—Cl4	3.5 (3)
C1—N1—C7—C8	−179.69 (19)	C14—N3—C20—C21	175.9 (2)
C1—N1—C7—C12	−1.3 (3)	C14—N3—C20—C25	−5.1 (3)
N1—C7—C8—C9	−177.60 (19)	N3—C20—C21—C22	178.9 (2)
C12—C7—C8—C9	3.9 (3)	C25—C20—C21—C22	−0.2 (3)
N1—C7—C8—C13	4.4 (3)	N3—C20—C21—C26	−2.5 (3)
C12—C7—C8—C13	−174.09 (18)	C25—C20—C21—C26	178.5 (2)
C13—C8—C9—N2	−2.5 (3)	C26—C21—C22—N4	2.5 (3)
C7—C8—C9—N2	179.58 (19)	C20—C21—C22—N4	−178.8 (2)
C13—C8—C9—C10	175.95 (18)	C26—C21—C22—C23	−178.1 (2)
C7—C8—C9—C10	−2.0 (3)	C20—C21—C22—C23	0.5 (3)
N2—C9—C10—O2	−1.2 (3)	N4—C22—C23—O4	1.6 (3)
C8—C9—C10—O2	−179.80 (19)	C21—C22—C23—O4	−177.8 (2)
N2—C9—C10—C11	177.42 (18)	N4—C22—C23—C24	179.7 (2)
C8—C9—C10—C11	−1.2 (3)	C21—C22—C23—C24	0.3 (3)
O2—C10—C11—C12	−178.9 (2)	O4—C23—C24—C25	176.6 (2)
C9—C10—C11—C12	2.5 (3)	C22—C23—C24—C25	−1.5 (3)
C10—C11—C12—C7	−0.6 (3)	C23—C24—C25—C20	1.9 (4)
N1—C7—C12—C11	178.9 (2)	N3—C20—C25—C24	179.9 (2)
C8—C7—C12—C11	−2.7 (3)	C21—C20—C25—C24	−1.0 (3)
C9—C8—C13—O1	3.6 (3)	C22—C21—C26—O3	−2.6 (4)
C7—C8—C13—O1	−178.44 (19)	C20—C21—C26—O3	178.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2X···Cl1i	0.92 (1)	2.60 (1)	3.4590 (18)	156.(2)
N2—H2Y···O1	0.92 (1)	2.08 (2)	2.722 (2)	126.(2)
N2—H2Y···O4i	0.92 (1)	2.26 (2)	2.933 (2)	130.(2)
N4—H4X···O1i	0.93 (1)	2.04 (1)	2.916 (2)	155 (2)
N4—H4Y···O3	0.92 (1)	2.01 (2)	2.666 (3)	127.(2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2X⋯Cl1i	0.92 (1)	2.60 (1)	3.4590 (18)	156 (2)
N2—H2Y⋯O1	0.92 (1)	2.08 (2)	2.722 (2)	126 (2)
N2—H2Y⋯O4i	0.92 (1)	2.26 (2)	2.933 (2)	130 (2)
N4—H4X⋯O1i	0.93 (1)	2.04 (1)	2.916 (2)	155 (2)
N4—H4Y⋯O3	0.92 (1)	2.01 (2)	2.666 (3)	127 (2)

Symmetry code: (i) .