N,N′-Bis­[(4-ethoxy­phenyl)­amino­acetyl]-4,5-di­methyl-o-phenyl­enedi­amine

All interatomic distances in the title compound, C₂₈H₃₄N₄O₄, are normal. The (4-ethoxy­phenyl)­amino parts of the side branches are almost ideally planar. The overall arrangement of the side branches seems to be imposed by hydrogen bonds. The substituents are stabilized by interbranch N—H...O hydrogen bonds. The structure of the title compound is assembled by intermolecular N—H...O hydrogen bonds, forming a two-dimensional framework.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.048
• wR factor = 0.175
• Data-to-parameter ratio = 17.0

checkCIF results

No syntax errors found



ADDSYM reports no extra symmetry


 Alert Level C:



RADNW_01  Alert C The radiation wavelength lies outside the expected range
          for the supplied radiation type. Expected range 1.54175-1.54180
          Wavelength given =    1.54052

General Notes



RADNW_01  The radiation wavelength given implies that Cu Kalpha1 has
          been used. Please check that this is correct.
          Wavelength given =    1.54052


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

S1. Comment

The present work is a continuation of our previous studies on derivatives of 2,3,4,5,6,7-hexahydro-1H-1,4,7-benzotriazone-2,5-dione. Upon introduction of pharmacophoric substituents for a desired activity into those systems, it is expected that derivatives will be obtained exhibiting numerous favourable properties, such as analeptic activity or possible anticancer and anti-HIV activities (Bartczak et al., 1995). Within this area of research, the preliminary results of determining the crystal structure of the title compound were previously published (Mikiciuk-Olasik et al., 1993), but the complete structure was never determined. Thus, we now present a full structure of the N,N'-bis[(4-ethoxyphenyl)aminoacetyl]-4,5-dimethyl-o-phenylenediamine [Cambridge Structural Database (CSD; Allen and Kennard, 1993) refcode: WEWPIX (the preliminary studies)].

The perspective view of the title compound, (III), together with the atom-numbering scheme is shown in Fig. 1. A l l interatomic distances can be considered normal. Atoms C7, C8 and C30 show signs of disorder (particularly high values of U_eq), but all attempts to find model of disorder fail. Thus, it can be supposed dynamical character of disorder. The all atoms of the (4-ethoxyphenyl)amino parts of the respective side branches are almost coplanar. The maximum deviation in the N11 branch is 0.058 (2) Å for O12 (branch A hereafter) and the maximum deviation in the N21 branch is 0.046 (2) Å for O22 (branch B hereafter). The next bonded C atom Cx2 deviates by 0.740 (2) and 0.425 (2) Å from the above planes, respectively (where x = 1 for the atoms of the branch A and x = 2 for the atoms of the branch B). These planes make a dihedral angle of 27.37 (5)°. The main difference between branches A and B is the conformation of the chain consisting of Nx1, Cx1, Cx2 and Nx2 (best described by the torsion angles, see Table 1 for details). The overall arrangement of the side branches seems to be imposed partly by the N12—H12···O11 hydrogen bond and the C5—H5···O21 weak hydrogen bond (Desiraju & Steiner, 1999) (branch A), and by the N21—H21···N22 hydrogen bond (branch B); for details, see Table 2. The substituents are stabilized by interbranch N21—H21···O11 hydrogen bond (Jeffrey & Saenger, 1994). The N21 atom acts as a donor for two intramolecular hydrogen bonds and these hydrogen bonds are created via the same hydrogen atom (H21). The structure of the title compound is assembled by intermolecular N—H···O hydrogen bonds, to form a two-dimensional framework (Fig. 2 and Table 2). There are no unusual intermolecular short contacts, except for the hydrogen bonds described in Table 2.

S2. Experimental

Compound (III) was prepared according to the method depicted on Scheme 1. A mixture 0.015 mol (4.00 g) of (I) and 0.030 mol (4.20 g) of p-phenetidine in 600 ml of anhydrous etanol in the presence of anhydrous sodium carbonate (0.075 mol, 8.00 g) was heated under reflux for 10 h (Mikiciuk-Olasik et al., 1993, 1994). The mixture was filtered and the solvent was distilled off. Compounds (II), (III) and a small amount of (IV) were isolated by fractional crystallization of the solid residue. Data for (III): yield 20%; m.p. 454.2 K. Elemental analyis (calculated/found): C 68.55/68.53%, H 6.98/7.09%, N 11.42/11.24%. IR (cm^-1): 3200, 1590 (NH); 1670, 1520 (NH—CO). ¹H NMR (in DMSO/TMS, chemical shifts in p.p.m.): 1.4 (t,6H, 2CH₃CH₂, J = 7 Hz), 2.35 (s, 6H, 2CH₃Ph), 3.7 (d, 4H, 2CH₂NH, J = 6 Hz), 4.05 (q, 4H, 2CH₂CH₃, J = 7 Hz), 5.65 (t,2H, 2NHCH₂, J = 6 Hz) 6.9 (m, 10 H_ar), 9.6 (s, 2 H, NHCO).

S3. Refinement

Because collected data were relatively weak, there is a large amount of reflections with small intensities, and thus a part of reflections was marked as unobserved. This affect fraction of unique reflections observed (out to θ = 80.79°) which is equal to 96%.

All H atoms, except of these bonded to N atoms, were set in calculated positions. The H atoms bonded to N atoms were located in difference Fourier syntheses, calculated after four cycles of anistropic refinement. All H atoms were treated as riding on the adjacent C atom. The methyl groups were allowed to rotate about their local threefold axis.

Computing details

Data collection: KM-4 Software (Kuma, 1993); cell refinement: KM-4 Software; data reduction: DATAPROC (Gałdecki et al., 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1990b) and ORTEP-3 (Farrugia, 1997).

Figures

	Fig. 1. The molecular structure of title compound (III). Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity.
	Fig. 2. The part of the molecular packing of (III) showing intermolecular hydrogen bonds creating a two-dimensional net structure. Carbon-bonded H atoms have been omitted for clarity. Hydrogen bonds are indicated by dashed lines.

N,N'-Bis[(4-ethoxyphenyl)aminoacetyl]-4,5-dimethyl-o-phenylenediamine

Crystal data

C28H34N4O4	F(000) = 1048
Mr = 490.59	Dx = 1.225 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54052 Å
a = 14.6542 (11) Å	Cell parameters from 99 reflections
b = 14.3344 (14) Å	θ = 5–60°
c = 12.7220 (12) Å	µ = 0.67 mm^−1
β = 95.606 (9)°	T = 293 K
V = 2659.6 (4) Å^3	Sphere, colourless
Z = 4	0.46 mm (radius)

Data collection

Kuma KM-4 diffractometer	3352 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.040
Graphite monochromator	θmax = 80.8°, θmin = 3.0°
ω–2θ scans	h = −18→18
Absorption correction: numerical X-RED. Stoe & Cie (1999)	k = −18→0
Tmin = 0.713, Tmax = 0.789	l = −16→0
6127 measured reflections	2 standard reflections every 100 reflections
5857 independent reflections	intensity decay: −3.1%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.175	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.1016P)^2] where P = (Fo^2 + 2Fc^2)/3
5857 reflections	(Δ/σ)max = 0.001
345 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.42 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N11	0.84417 (12)	0.11954 (12)	0.21384 (13)	0.0456 (4)
H11	0.8428 (18)	0.1569 (19)	0.156 (2)	0.072 (8)*
N12	1.02773 (13)	−0.03087 (13)	0.14878 (16)	0.0529 (5)
H12	1.0132 (18)	−0.063 (2)	0.206 (2)	0.073 (8)*
N22	1.04211 (14)	0.11570 (14)	0.50303 (15)	0.0559 (5)
H22	1.0650 (18)	0.071 (2)	0.542 (2)	0.074 (8)*
N21	0.86368 (13)	0.13160 (13)	0.43812 (13)	0.0478 (4)
H21	0.9119 (17)	0.0977 (18)	0.4173 (19)	0.064 (7)*
C11	0.90943 (14)	0.05421 (13)	0.22644 (14)	0.0410 (4)
O11	0.91098 (10)	−0.00658 (10)	0.29543 (11)	0.0508 (4)
C12	0.98489 (15)	0.06012 (14)	0.15401 (16)	0.0468 (5)
H12A	0.9597	0.0793	0.0840	0.056*
H12B	1.0301	0.1059	0.1807	0.056*
C13	1.12020 (15)	−0.03765 (14)	0.13222 (16)	0.0474 (5)
C14	1.16247 (16)	0.02484 (17)	0.06861 (18)	0.0561 (5)
H14	1.1288	0.0738	0.0363	0.067*
C15	1.25334 (17)	0.01484 (19)	0.0531 (2)	0.0630 (6)
H15	1.2803	0.0574	0.0104	0.076*
C16	1.30561 (15)	−0.05708 (17)	0.09968 (19)	0.0559 (5)
C17	1.26422 (17)	−0.11996 (16)	0.1618 (2)	0.0615 (6)
H17	1.2980	−0.1692	0.1932	0.074*
C18	1.17292 (17)	−0.11017 (16)	0.1775 (2)	0.0596 (6)
H18	1.1460	−0.1533	0.2196	0.072*
O22	1.27930 (12)	0.24313 (14)	0.21812 (15)	0.0742 (5)
C19	1.45375 (18)	−0.1258 (2)	0.1353 (3)	0.0798 (8)
H19A	1.4326	−0.1887	0.1189	0.096*
H19B	1.4527	−0.1158	0.2105	0.096*
C20	1.54883 (18)	−0.1138 (2)	0.1055 (3)	0.0856 (9)
H20A	1.5872	−0.1623	0.1374	0.128*
H20B	1.5722	−0.0542	0.1299	0.128*
H20C	1.5484	−0.1170	0.0301	0.128*
C21	0.88984 (17)	0.18740 (15)	0.51997 (15)	0.0508 (5)
O21	0.83888 (13)	0.24215 (13)	0.55980 (14)	0.0735 (5)
C22	0.98910 (17)	0.17713 (18)	0.56309 (17)	0.0592 (6)
H22A	1.0175	0.2383	0.5657	0.071*
H22B	0.9914	0.1539	0.6349	0.071*
C23	1.09861 (15)	0.15168 (15)	0.42914 (16)	0.0499 (5)
C24	1.08878 (17)	0.24018 (15)	0.38781 (18)	0.0554 (5)
H24	1.0425	0.2788	0.4079	0.066*
C25	1.14737 (16)	0.27251 (17)	0.3162 (2)	0.0594 (6)
H25	1.1401	0.3326	0.2890	0.071*
C26	1.21589 (16)	0.21646 (18)	0.28515 (19)	0.0581 (6)
C27	1.22402 (17)	0.12631 (17)	0.3228 (2)	0.0616 (6)
H27	1.2688	0.0871	0.3003	0.074*
C28	1.16621 (17)	0.09416 (16)	0.3935 (2)	0.0600 (6)
H28	1.1721	0.0331	0.4180	0.072*
O12	1.39578 (11)	−0.06082 (14)	0.07858 (16)	0.0763 (5)
C29	1.2681 (2)	0.3325 (2)	0.1692 (3)	0.0807 (8)
H29A	1.2708	0.3810	0.2225	0.097*
H29B	1.2090	0.3361	0.1277	0.097*
C30	1.3430 (2)	0.3454 (3)	0.1000 (3)	0.1025 (12)
H30A	1.3368	0.4053	0.0662	0.154*
H30B	1.3396	0.2973	0.0473	0.154*
H30C	1.4012	0.3421	0.1417	0.154*
C1	0.76626 (13)	0.12260 (13)	0.27291 (16)	0.0435 (4)
C6	0.77559 (14)	0.12718 (13)	0.38237 (15)	0.0440 (4)
C5	0.69742 (17)	0.12808 (16)	0.4351 (2)	0.0591 (6)
H5	0.7034	0.1291	0.5086	0.071*
C4	0.61043 (17)	0.12750 (16)	0.3814 (3)	0.0666 (7)
C3	0.60123 (16)	0.12781 (18)	0.2717 (2)	0.0680 (7)
C2	0.67977 (16)	0.12368 (17)	0.2198 (2)	0.0601 (6)
H2	0.6740	0.1216	0.1464	0.072*
C7	0.5083 (2)	0.1321 (3)	0.2096 (4)	0.1143 (14)
H7A	0.4762	0.1866	0.2298	0.171*
H7B	0.4738	0.0773	0.2238	0.171*
H7C	0.5157	0.1350	0.1355	0.171*
C8	0.5283 (2)	0.1255 (2)	0.4459 (4)	0.1080 (13)
H8A	0.5493	0.1253	0.5198	0.162*
H8B	0.4928	0.0702	0.4289	0.162*
H8C	0.4909	0.1796	0.4297	0.162*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0532 (9)	0.0457 (9)	0.0388 (8)	0.0084 (8)	0.0084 (7)	0.0050 (7)
N12	0.0510 (10)	0.0451 (10)	0.0655 (12)	0.0029 (8)	0.0200 (9)	−0.0016 (9)
N22	0.0651 (12)	0.0507 (10)	0.0510 (10)	0.0043 (9)	0.0013 (9)	0.0081 (9)
N21	0.0565 (10)	0.0498 (10)	0.0375 (8)	0.0048 (8)	0.0071 (7)	−0.0063 (7)
C11	0.0488 (10)	0.0365 (9)	0.0379 (9)	0.0017 (8)	0.0053 (8)	−0.0026 (7)
O11	0.0651 (9)	0.0435 (7)	0.0456 (7)	0.0102 (7)	0.0145 (7)	0.0068 (6)
C12	0.0556 (12)	0.0425 (10)	0.0434 (10)	0.0033 (9)	0.0107 (9)	0.0017 (8)
C13	0.0543 (11)	0.0417 (10)	0.0474 (11)	0.0004 (9)	0.0102 (9)	−0.0047 (8)
C14	0.0533 (12)	0.0603 (13)	0.0555 (13)	0.0068 (10)	0.0088 (10)	0.0122 (10)
C15	0.0582 (14)	0.0683 (15)	0.0642 (14)	0.0016 (12)	0.0155 (11)	0.0157 (12)
C16	0.0485 (12)	0.0547 (12)	0.0655 (13)	0.0031 (10)	0.0111 (10)	0.0022 (10)
C17	0.0598 (14)	0.0466 (12)	0.0798 (16)	0.0081 (10)	0.0151 (12)	0.0087 (11)
C18	0.0622 (14)	0.0478 (12)	0.0721 (15)	0.0025 (10)	0.0236 (12)	0.0079 (11)
O22	0.0676 (11)	0.0784 (12)	0.0792 (12)	0.0094 (9)	0.0200 (10)	0.0166 (10)
C19	0.0602 (15)	0.0691 (17)	0.112 (2)	0.0124 (13)	0.0162 (15)	0.0152 (16)
C20	0.0543 (14)	0.087 (2)	0.116 (2)	0.0091 (14)	0.0095 (15)	0.0121 (18)
C21	0.0719 (14)	0.0493 (11)	0.0320 (9)	−0.0004 (10)	0.0092 (9)	0.0001 (8)
O21	0.0829 (12)	0.0740 (12)	0.0649 (10)	0.0080 (9)	0.0134 (9)	−0.0281 (9)
C22	0.0723 (15)	0.0632 (14)	0.0407 (10)	−0.0007 (12)	−0.0018 (10)	−0.0030 (10)
C23	0.0569 (12)	0.0453 (11)	0.0451 (10)	0.0019 (9)	−0.0064 (9)	0.0008 (8)
C24	0.0590 (12)	0.0479 (12)	0.0584 (13)	0.0074 (10)	0.0019 (10)	0.0048 (10)
C25	0.0615 (13)	0.0512 (12)	0.0649 (14)	0.0067 (11)	0.0030 (11)	0.0101 (11)
C26	0.0552 (13)	0.0609 (13)	0.0572 (13)	0.0018 (11)	0.0010 (10)	0.0028 (11)
C27	0.0592 (13)	0.0570 (14)	0.0684 (15)	0.0129 (11)	0.0066 (11)	0.0015 (11)
C28	0.0662 (14)	0.0447 (11)	0.0679 (14)	0.0087 (10)	0.0000 (12)	0.0035 (10)
O12	0.0483 (9)	0.0812 (12)	0.1014 (14)	0.0065 (8)	0.0171 (9)	0.0273 (11)
C29	0.0644 (16)	0.093 (2)	0.0837 (19)	0.0072 (15)	0.0042 (14)	0.0300 (16)
C30	0.078 (2)	0.132 (3)	0.102 (2)	0.005 (2)	0.0269 (18)	0.044 (2)
C1	0.0459 (10)	0.0372 (9)	0.0481 (10)	0.0049 (8)	0.0084 (8)	−0.0021 (8)
C6	0.0475 (10)	0.0402 (10)	0.0455 (10)	0.0030 (8)	0.0109 (8)	0.0000 (8)
C5	0.0672 (15)	0.0525 (12)	0.0615 (13)	0.0017 (11)	0.0254 (12)	0.0025 (10)
C4	0.0555 (13)	0.0457 (12)	0.103 (2)	0.0029 (10)	0.0302 (14)	−0.0008 (13)
C3	0.0475 (12)	0.0561 (14)	0.099 (2)	0.0056 (10)	0.0013 (13)	−0.0187 (13)
C2	0.0542 (13)	0.0564 (13)	0.0675 (14)	0.0109 (10)	−0.0045 (11)	−0.0123 (11)
C7	0.0560 (16)	0.122 (3)	0.159 (4)	0.0217 (18)	−0.020 (2)	−0.045 (3)
C8	0.0648 (18)	0.089 (2)	0.181 (4)	0.0046 (16)	0.070 (2)	0.010 (2)

Geometric parameters (Å, º)

N11—C11	1.337 (2)	C21—O21	1.226 (3)
N11—C1	1.427 (2)	C21—C22	1.511 (3)
N11—H11	0.91 (3)	C22—H22A	0.9700
N12—C13	1.395 (3)	C22—H22B	0.9700
N12—C12	1.452 (3)	C23—C24	1.375 (3)
N12—H12	0.91 (3)	C23—C28	1.398 (3)
N22—C23	1.410 (3)	C24—C25	1.391 (3)
N22—C22	1.442 (3)	C24—H24	0.9300
N22—H22	0.85 (3)	C25—C26	1.374 (3)
N21—C21	1.339 (3)	C25—H25	0.9300
N21—C6	1.412 (3)	C26—C27	1.380 (3)
N21—H21	0.92 (3)	C27—C28	1.374 (3)
C11—O11	1.235 (2)	C27—H27	0.9300
C11—C12	1.509 (3)	C28—H28	0.9300
C12—H12A	0.9700	C29—C30	1.485 (4)
C12—H12B	0.9700	C29—H29A	0.9700
C13—C18	1.387 (3)	C29—H29B	0.9700
C13—C14	1.392 (3)	C30—H30A	0.9600
C14—C15	1.372 (3)	C30—H30B	0.9600
C14—H14	0.9300	C30—H30C	0.9600
C15—C16	1.383 (3)	C1—C2	1.377 (3)
C15—H15	0.9300	C1—C6	1.387 (3)
C16—O12	1.375 (3)	C6—C5	1.383 (3)
C16—C17	1.378 (3)	C5—C4	1.386 (4)
C17—C18	1.379 (3)	C5—H5	0.9300
C17—H17	0.9300	C4—C3	1.389 (4)
C18—H18	0.9300	C4—C8	1.522 (3)
O22—C26	1.375 (3)	C3—C2	1.383 (3)
O22—C29	1.427 (3)	C3—C7	1.508 (4)
C19—O12	1.410 (3)	C2—H2	0.9300
C19—C20	1.489 (4)	C7—H7A	0.9600
C19—H19A	0.9700	C7—H7B	0.9600
C19—H19B	0.9700	C7—H7C	0.9600
C20—H20A	0.9600	C8—H8A	0.9600
C20—H20B	0.9600	C8—H8B	0.9600
C20—H20C	0.9600	C8—H8C	0.9600
C11—N11—C1	123.91 (17)	C24—C23—C28	118.1 (2)
C11—N11—H11	117.9 (17)	C24—C23—N22	123.1 (2)
C1—N11—H11	117.0 (17)	C28—C23—N22	118.8 (2)
C13—N12—C12	120.02 (18)	C23—C24—C25	120.6 (2)
C13—N12—H12	113.1 (17)	C23—C24—H24	119.7
C12—N12—H12	106.8 (17)	C25—C24—H24	119.7
C23—N22—C22	120.8 (2)	C26—C25—C24	120.6 (2)
C23—N22—H22	115.6 (18)	C26—C25—H25	119.7
C22—N22—H22	110.7 (19)	C24—C25—H25	119.7
C21—N21—C6	126.54 (19)	C25—C26—O22	124.9 (2)
C21—N21—H21	111.8 (16)	C25—C26—C27	119.3 (2)
C6—N21—H21	121.5 (16)	O22—C26—C27	115.8 (2)
O11—C11—N11	122.85 (18)	C28—C27—C26	120.3 (2)
O11—C11—C12	120.64 (17)	C28—C27—H27	119.9
N11—C11—C12	116.46 (17)	C26—C27—H27	119.9
N12—C12—C11	108.87 (17)	C27—C28—C23	121.1 (2)
N12—C12—H12A	109.9	C27—C28—H28	119.5
C11—C12—H12A	109.9	C23—C28—H28	119.5
N12—C12—H12B	109.9	C16—O12—C19	117.9 (2)
C11—C12—H12B	109.9	O22—C29—C30	108.1 (3)
H12A—C12—H12B	108.3	O22—C29—H29A	110.1
C18—C13—C14	117.5 (2)	C30—C29—H29A	110.1
C18—C13—N12	120.0 (2)	O22—C29—H29B	110.1
C14—C13—N12	122.5 (2)	C30—C29—H29B	110.1
C15—C14—C13	120.6 (2)	H29A—C29—H29B	108.4
C15—C14—H14	119.7	C29—C30—H30A	109.5
C13—C14—H14	119.7	C29—C30—H30B	109.5
C14—C15—C16	121.4 (2)	H30A—C30—H30B	109.5
C14—C15—H15	119.3	C29—C30—H30C	109.5
C16—C15—H15	119.3	H30A—C30—H30C	109.5
O12—C16—C17	124.9 (2)	H30B—C30—H30C	109.5
O12—C16—C15	116.6 (2)	C2—C1—C6	119.20 (19)
C17—C16—C15	118.5 (2)	C2—C1—N11	119.15 (19)
C16—C17—C18	120.3 (2)	C6—C1—N11	121.62 (18)
C16—C17—H17	119.9	C5—C6—C1	118.8 (2)
C18—C17—H17	119.9	C5—C6—N21	121.04 (19)
C17—C18—C13	121.7 (2)	C1—C6—N21	120.11 (17)
C17—C18—H18	119.2	C6—C5—C4	121.7 (2)
C13—C18—H18	119.2	C6—C5—H5	119.1
C26—O22—C29	117.6 (2)	C4—C5—H5	119.1
O12—C19—C20	109.0 (2)	C5—C4—C3	119.3 (2)
O12—C19—H19A	109.9	C5—C4—C8	118.2 (3)
C20—C19—H19A	109.9	C3—C4—C8	122.5 (3)
O12—C19—H19B	109.9	C2—C3—C4	118.4 (2)
C20—C19—H19B	109.9	C2—C3—C7	120.2 (3)
H19A—C19—H19B	108.3	C4—C3—C7	121.4 (3)
C19—C20—H20A	109.5	C1—C2—C3	122.3 (2)
C19—C20—H20B	109.5	C1—C2—H2	118.8
H20A—C20—H20B	109.5	C3—C2—H2	118.8
C19—C20—H20C	109.5	C3—C7—H7A	109.5
H20A—C20—H20C	109.5	C3—C7—H7B	109.5
H20B—C20—H20C	109.5	H7A—C7—H7B	109.5
O21—C21—N21	124.3 (2)	C3—C7—H7C	109.5
O21—C21—C22	121.1 (2)	H7A—C7—H7C	109.5
N21—C21—C22	114.61 (19)	H7B—C7—H7C	109.5
N22—C22—C21	114.62 (18)	C4—C8—H8A	109.5
N22—C22—H22A	108.6	C4—C8—H8B	109.5
C21—C22—H22A	108.6	H8A—C8—H8B	109.5
N22—C22—H22B	108.6	C4—C8—H8C	109.5
C21—C22—H22B	108.6	H8A—C8—H8C	109.5
H22A—C22—H22B	107.6	H8B—C8—H8C	109.5
C6—C1—N11—C11	57.6 (3)	N21—C21—C22—N22	5.8 (3)
C1—N11—C11—C12	177.75 (18)	C21—C22—N22—C23	98.6 (3)
N11—C11—C12—N12	−158.31 (18)	C22—N22—C23—C24	−18.6 (3)
C11—C12—N12—C13	−149.63 (19)	C15—C16—O12—C19	172.0 (3)
C12—N12—C13—C14	−34.7 (3)	C16—O12—C19—C20	−176.3 (3)
C1—C6—N21—C21	136.3 (2)	C25—C26—O22—C29	−6.2 (4)
C6—N21—C21—C22	−179.5 (2)	C26—O22—C29—C30	−179.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O21^i	0.91 (3)	1.89 (3)	2.783 (2)	166 (2)
N12—H12···O11	0.91 (3)	2.13 (3)	2.675 (2)	118 (2)
N22—H22···O11^ii	0.85 (3)	2.27 (3)	3.025 (2)	148 (3)
N21—H21···N22	0.92 (3)	2.12 (3)	2.674 (3)	118 (2)
N21—H21···O11	0.92 (3)	2.15 (3)	2.819 (2)	129 (2)
C5—H5···O21	0.93	2.60	2.974 (3)	105

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+2, −y, −z+1.