1,3-Bis(2-ethoxy-phen-yl)triazene.

The title compound, C(16)H(19)N(3)O(2), exhibits a trans geometry about the N=N double bond in the triazene unit in the solid state, and individual mol-ecules are close to planar with r.m.s. deviations from planarity of 0.065 Å and 0.242 Å for the two independent molecules in the asymmetric unit. Distinct inter-molecular N-H⋯N hydrogen bonds lead to the formation of dimers with an R(2) (2)(8) graph-set motif. The steric demands of the eth-oxy groups in the ortho position prevent a coplanar arrangement of the two mol-ecules in the dimers and these instead consist of two inter-locked mol-ecules that are related by a non-crystallographic pseudo-twofold rotation axis. Weak C-H⋯π inter-actions between the CH groups and the aromatic phenyl rings also occur.

Related literature

For aryl triazenes, their structural properties and metal complexes, see: Meldola et al. (1888 ▶); Leman et al. (1993 ▶); Chen et al. (2002 ▶); Vrieze et al. (1987 ▶). For a similar structure with cyano instead of eth­oxy groups, see: Melardi et al. (2008 ▶). For the synthesis and characterization of a similar structure with meth­oxy instead of eth­oxy groups, see: Rofouei et al. (2006 ▶). For the synthesis and crystal structures of mercury(II) and silver(I) complexes with 1,3-bis­(2-methoxy­phen­yl)tri­azene, see: Hematyar et al. (2008 ▶) and Payehghadr et al. (2007 ▶), respectively. For the investigation of hydrogen-bond patterns and related graph sets, see: Grell et al. (2002 ▶).

Experimental

Crystal data

C16H19N3O2

M = 285.34

Triclinic,

a = 11.3971 (7) Å

b = 11.8696 (7) Å

c = 14.0627 (9) Å

α = 106.467 (5)°

β = 98.598 (5)°

γ = 116.512 (5)°

V = 1545.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 120 K

0.30 × 0.20 × 0.15 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.973, T max = 0.982

17109 measured reflections

8181 independent reflections

4988 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.138

S = 1.00

8181 reflections

383 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809008034/zl2178sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008034/zl2178Isup2.hkl

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

C16H19N3O2	Z = 4
Mr = 285.34	F(000) = 608
Triclinic, P1	Dx = 1.226 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.3971 (7) Å	Cell parameters from 887 reflections
b = 11.8696 (7) Å	θ = 3–30°
c = 14.0627 (9) Å	µ = 0.08 mm−1
α = 106.467 (5)°	T = 120 K
β = 98.598 (5)°	Prism, orange
γ = 116.512 (5)°	0.30 × 0.20 × 0.15 mm
V = 1545.7 (2) Å3

Bruker SMART 1000 CCD area-detector diffractometer	8181 independent reflections
Radiation source: fine-focus sealed tube	4988 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 29.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −15→15
Tmin = 0.973, Tmax = 0.982	k = −16→16
17109 measured reflections	l = −19→19

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)] = 0.058	Hydrogen site location: mixed
wR(F2) = 0.138	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0517P)2 + 0.497P] where P = (Fo2 + 2Fc2)/3
8181 reflections	(Δ/σ)max < 0.001
383 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.31 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
N1	0.65754 (14)	0.89887 (15)	0.26280 (11)	0.0273 (3)
H1N	0.6187	0.8521	0.3017	0.033*
N2	0.57346 (14)	0.91539 (14)	0.20038 (10)	0.0247 (3)
N3	0.44508 (14)	0.83193 (14)	0.18591 (11)	0.0253 (3)
O1	0.81959 (12)	0.82358 (12)	0.34265 (9)	0.0309 (3)
O2	0.17841 (12)	0.66700 (12)	0.14955 (9)	0.0308 (3)
C1	0.80038 (16)	0.98331 (17)	0.28546 (12)	0.0244 (4)
C2	0.88658 (17)	0.94198 (17)	0.32698 (13)	0.0256 (4)
C3	1.02882 (17)	1.01982 (18)	0.34861 (14)	0.0304 (4)
H3A	1.0873	0.9918	0.3765	0.036*
C4	1.08542 (18)	1.13829 (18)	0.32955 (14)	0.0323 (4)
H4A	1.1827	1.1913	0.3445	0.039*
C5	1.00087 (18)	1.17975 (18)	0.28886 (14)	0.0317 (4)
H5A	1.0401	1.2610	0.2758	0.038*
C6	0.85879 (17)	1.10262 (17)	0.26714 (13)	0.0277 (4)
H6A	0.8010	1.1315	0.2396	0.033*
C7	0.90069 (18)	0.77429 (18)	0.38370 (14)	0.0314 (4)
H7A	0.9703	0.8444	0.4523	0.038*
H7B	0.9498	0.7535	0.3353	0.038*
C8	0.8034 (2)	0.6466 (2)	0.39582 (15)	0.0386 (5)
H8A	0.8561	0.6107	0.4247	0.058*
H8B	0.7358	0.5775	0.3273	0.058*
H8C	0.7548	0.6682	0.4434	0.058*
C9	0.35033 (16)	0.84446 (16)	0.11871 (12)	0.0217 (3)
C10	0.20907 (17)	0.75634 (16)	0.10018 (13)	0.0244 (3)
C11	0.10996 (17)	0.76308 (17)	0.03477 (13)	0.0278 (4)
H11A	0.0143	0.7043	0.0226	0.033*
C12	0.15150 (18)	0.85612 (18)	−0.01262 (14)	0.0294 (4)
H12A	0.0837	0.8594	−0.0582	0.035*
C13	0.29049 (18)	0.94394 (17)	0.00583 (13)	0.0279 (4)
H13A	0.3180	1.0074	−0.0268	0.034*
C14	0.38903 (17)	0.93889 (17)	0.07190 (12)	0.0245 (3)
H14A	0.4845	1.0006	0.0857	0.029*
C15	0.03901 (18)	0.59545 (18)	0.14986 (14)	0.0310 (4)
H15A	−0.0245	0.5332	0.0776	0.037*
H15B	0.0101	0.6613	0.1796	0.037*
C16	0.0351 (2)	0.5146 (2)	0.21591 (15)	0.0396 (5)
H16A	−0.0596	0.4627	0.2168	0.059*
H16B	0.0970	0.5775	0.2876	0.059*
H16C	0.0656	0.4511	0.1864	0.059*
N4	0.50110 (14)	0.71697 (14)	0.36671 (10)	0.0249 (3)
N5	0.42582 (13)	0.58882 (14)	0.30543 (10)	0.0230 (3)
N6	0.39770 (14)	0.57030 (13)	0.20569 (10)	0.0246 (3)
H6N	0.4166	0.6468	0.1933	0.030*
O3	0.65249 (12)	0.97589 (11)	0.49894 (9)	0.0283 (3)
O4	0.36188 (12)	0.53622 (11)	0.00756 (8)	0.0262 (3)
C17	0.52863 (16)	0.74425 (16)	0.47504 (12)	0.0220 (3)
C18	0.60555 (16)	0.88364 (17)	0.54400 (13)	0.0238 (3)
C19	0.62867 (17)	0.91875 (18)	0.65110 (13)	0.0277 (4)
H19A	0.6786	1.0125	0.6978	0.033*
C20	0.57898 (18)	0.81711 (19)	0.68985 (13)	0.0305 (4)
H20A	0.5950	0.8417	0.7630	0.037*
C21	0.50605 (18)	0.67988 (19)	0.62246 (13)	0.0303 (4)
H21A	0.4743	0.6106	0.6494	0.036*
C22	0.47978 (17)	0.64436 (17)	0.51545 (13)	0.0261 (4)
H22A	0.4276	0.5503	0.4692	0.031*
C23	0.70481 (18)	1.11735 (17)	0.56228 (13)	0.0290 (4)
H23A	0.7870	1.1528	0.6224	0.035*
H23B	0.6332	1.1272	0.5895	0.035*
C24	0.74328 (19)	1.19540 (18)	0.49298 (14)	0.0328 (4)
H24A	0.7725	1.2913	0.5318	0.049*
H24B	0.6629	1.1546	0.4309	0.049*
H24C	0.8194	1.1910	0.4713	0.049*
C25	0.31797 (16)	0.43556 (16)	0.12976 (12)	0.0217 (3)
C26	0.30226 (16)	0.41821 (16)	0.02469 (12)	0.0222 (3)
C27	0.22978 (17)	0.28660 (17)	−0.05366 (13)	0.0251 (4)
H27A	0.2193	0.2742	−0.1248	0.030*
C28	0.17266 (17)	0.17315 (17)	−0.02762 (13)	0.0274 (4)
H28A	0.1229	0.0834	−0.0813	0.033*
C29	0.18774 (17)	0.19007 (17)	0.07571 (13)	0.0269 (4)
H29A	0.1484	0.1122	0.0929	0.032*
C30	0.26063 (16)	0.32121 (17)	0.15456 (13)	0.0243 (3)
H30A	0.2713	0.3328	0.2256	0.029*
C31	0.35336 (17)	0.52266 (17)	−0.09816 (12)	0.0250 (4)
H31A	0.2552	0.4705	−0.1429	0.030*
H31B	0.3990	0.4729	−0.1264	0.030*
C32	0.42454 (19)	0.66412 (18)	−0.09738 (14)	0.0319 (4)
H32A	0.4228	0.6579	−0.1686	0.048*
H32B	0.5208	0.7156	−0.0514	0.048*
H32C	0.3765	0.7112	−0.0716	0.048*

	U11	U22	U33	U12	U13	U23
N1	0.0217 (7)	0.0325 (8)	0.0272 (7)	0.0116 (6)	0.0069 (6)	0.0158 (6)
N2	0.0240 (7)	0.0241 (7)	0.0238 (7)	0.0121 (6)	0.0067 (6)	0.0079 (6)
N3	0.0201 (7)	0.0265 (7)	0.0267 (7)	0.0104 (6)	0.0061 (6)	0.0106 (6)
O1	0.0236 (6)	0.0315 (7)	0.0372 (7)	0.0129 (5)	0.0067 (5)	0.0170 (6)
O2	0.0227 (6)	0.0320 (7)	0.0383 (7)	0.0114 (5)	0.0107 (5)	0.0189 (6)
C1	0.0208 (8)	0.0277 (9)	0.0197 (8)	0.0104 (7)	0.0064 (6)	0.0066 (7)
C2	0.0225 (8)	0.0259 (9)	0.0239 (8)	0.0106 (7)	0.0073 (7)	0.0073 (7)
C3	0.0232 (9)	0.0350 (10)	0.0314 (9)	0.0156 (8)	0.0068 (7)	0.0109 (8)
C4	0.0202 (8)	0.0325 (10)	0.0338 (10)	0.0071 (8)	0.0093 (7)	0.0098 (8)
C5	0.0274 (9)	0.0282 (9)	0.0328 (10)	0.0090 (8)	0.0112 (8)	0.0116 (8)
C6	0.0255 (9)	0.0286 (9)	0.0277 (9)	0.0128 (8)	0.0085 (7)	0.0112 (7)
C7	0.0317 (10)	0.0348 (10)	0.0280 (9)	0.0203 (8)	0.0061 (8)	0.0095 (8)
C8	0.0453 (12)	0.0378 (11)	0.0335 (10)	0.0230 (10)	0.0090 (9)	0.0147 (9)
C9	0.0214 (8)	0.0211 (8)	0.0214 (8)	0.0116 (7)	0.0063 (6)	0.0059 (6)
C10	0.0241 (8)	0.0226 (8)	0.0260 (8)	0.0116 (7)	0.0100 (7)	0.0086 (7)
C11	0.0212 (8)	0.0252 (9)	0.0325 (9)	0.0112 (7)	0.0062 (7)	0.0080 (7)
C12	0.0273 (9)	0.0314 (10)	0.0327 (9)	0.0193 (8)	0.0057 (7)	0.0118 (8)
C13	0.0297 (9)	0.0267 (9)	0.0303 (9)	0.0162 (8)	0.0100 (7)	0.0121 (7)
C14	0.0219 (8)	0.0234 (8)	0.0270 (9)	0.0112 (7)	0.0087 (7)	0.0087 (7)
C15	0.0246 (9)	0.0292 (9)	0.0327 (10)	0.0101 (8)	0.0117 (7)	0.0088 (8)
C16	0.0380 (11)	0.0346 (11)	0.0339 (10)	0.0085 (9)	0.0141 (9)	0.0132 (9)
N4	0.0262 (7)	0.0235 (7)	0.0200 (7)	0.0110 (6)	0.0065 (6)	0.0056 (6)
N5	0.0222 (7)	0.0240 (7)	0.0226 (7)	0.0124 (6)	0.0073 (6)	0.0080 (6)
N6	0.0311 (8)	0.0194 (7)	0.0207 (7)	0.0117 (6)	0.0068 (6)	0.0074 (6)
O3	0.0328 (7)	0.0205 (6)	0.0257 (6)	0.0112 (5)	0.0091 (5)	0.0055 (5)
O4	0.0327 (7)	0.0221 (6)	0.0201 (6)	0.0118 (5)	0.0081 (5)	0.0074 (5)
C17	0.0213 (8)	0.0255 (8)	0.0215 (8)	0.0145 (7)	0.0068 (6)	0.0081 (7)
C18	0.0220 (8)	0.0262 (9)	0.0252 (8)	0.0139 (7)	0.0089 (7)	0.0095 (7)
C19	0.0259 (9)	0.0292 (9)	0.0231 (8)	0.0140 (8)	0.0062 (7)	0.0049 (7)
C20	0.0320 (10)	0.0398 (11)	0.0214 (8)	0.0206 (9)	0.0089 (7)	0.0108 (8)
C21	0.0332 (10)	0.0340 (10)	0.0288 (9)	0.0190 (8)	0.0120 (8)	0.0155 (8)
C22	0.0274 (9)	0.0252 (9)	0.0248 (8)	0.0137 (7)	0.0084 (7)	0.0085 (7)
C23	0.0275 (9)	0.0235 (9)	0.0289 (9)	0.0131 (7)	0.0046 (7)	0.0034 (7)
C24	0.0338 (10)	0.0253 (9)	0.0356 (10)	0.0151 (8)	0.0087 (8)	0.0088 (8)
C25	0.0196 (8)	0.0198 (8)	0.0234 (8)	0.0105 (7)	0.0057 (6)	0.0055 (6)
C26	0.0192 (8)	0.0208 (8)	0.0255 (8)	0.0102 (7)	0.0065 (6)	0.0082 (7)
C27	0.0240 (8)	0.0261 (9)	0.0217 (8)	0.0128 (7)	0.0055 (7)	0.0059 (7)
C28	0.0239 (9)	0.0205 (8)	0.0301 (9)	0.0105 (7)	0.0056 (7)	0.0031 (7)
C29	0.0221 (8)	0.0215 (8)	0.0351 (10)	0.0097 (7)	0.0101 (7)	0.0106 (7)
C30	0.0229 (8)	0.0277 (9)	0.0237 (8)	0.0135 (7)	0.0089 (7)	0.0104 (7)
C31	0.0245 (8)	0.0277 (9)	0.0203 (8)	0.0124 (7)	0.0077 (7)	0.0078 (7)
C32	0.0373 (10)	0.0334 (10)	0.0275 (9)	0.0181 (8)	0.0142 (8)	0.0133 (8)

N1—N2	1.3196 (18)	N4—N5	1.2896 (18)
N1—C1	1.401 (2)	N4—C17	1.418 (2)
N1—H1N	0.9100	N5—N6	1.3214 (18)
N2—N3	1.2909 (18)	N6—C25	1.403 (2)
N3—C9	1.414 (2)	N6—H6N	0.9100
O1—C2	1.369 (2)	O3—C18	1.3634 (19)
O1—C7	1.430 (2)	O3—C23	1.4380 (19)
O2—C10	1.3739 (19)	O4—C26	1.3684 (19)
O2—C15	1.430 (2)	O4—C31	1.4327 (18)
C1—C6	1.390 (2)	C17—C22	1.388 (2)
C1—C2	1.403 (2)	C17—C18	1.410 (2)
C2—C3	1.389 (2)	C18—C19	1.392 (2)
C3—C4	1.386 (2)	C19—C20	1.389 (2)
C3—H3A	0.9500	C19—H19A	0.9500
C4—C5	1.384 (3)	C20—C21	1.387 (2)
C4—H4A	0.9500	C20—H20A	0.9500
C5—C6	1.387 (2)	C21—C22	1.387 (2)
C5—H5A	0.9500	C21—H21A	0.9500
C6—H6A	0.9500	C22—H22A	0.9500
C7—C8	1.503 (3)	C23—C24	1.509 (2)
C7—H7A	0.9900	C23—H23A	0.9900
C7—H7B	0.9900	C23—H23B	0.9900
C8—H8A	0.9800	C24—H24A	0.9800
C8—H8B	0.9800	C24—H24B	0.9800
C8—H8C	0.9800	C24—H24C	0.9800
C9—C14	1.396 (2)	C25—C30	1.391 (2)
C9—C10	1.404 (2)	C25—C26	1.405 (2)
C10—C11	1.393 (2)	C26—C27	1.392 (2)
C11—C12	1.390 (2)	C27—C28	1.393 (2)
C11—H11A	0.9500	C27—H27A	0.9500
C12—C13	1.383 (2)	C28—C29	1.382 (2)
C12—H12A	0.9500	C28—H28A	0.9500
C13—C14	1.381 (2)	C29—C30	1.391 (2)
C13—H13A	0.9500	C29—H29A	0.9500
C14—H14A	0.9500	C30—H30A	0.9500
C15—C16	1.505 (3)	C31—C32	1.499 (2)
C15—H15A	0.9900	C31—H31A	0.9900
C15—H15B	0.9900	C31—H31B	0.9900
C16—H16A	0.9800	C32—H32A	0.9800
C16—H16B	0.9800	C32—H32B	0.9800
C16—H16C	0.9800	C32—H32C	0.9800
N2—N1—C1	117.93 (14)	N5—N4—C17	114.76 (13)
N2—N1—H1N	115.2	N4—N5—N6	111.94 (13)
C1—N1—H1N	124.3	N5—N6—C25	118.29 (13)
N3—N2—N1	111.87 (13)	N5—N6—H6N	115.3
N2—N3—C9	114.20 (13)	C25—N6—H6N	125.1
C2—O1—C7	118.23 (13)	C18—O3—C23	117.69 (13)
C10—O2—C15	117.52 (13)	C26—O4—C31	117.43 (12)
C6—C1—N1	123.34 (15)	C22—C17—C18	119.30 (15)
C6—C1—C2	119.40 (15)	C22—C17—N4	124.46 (15)
N1—C1—C2	117.25 (15)	C18—C17—N4	116.16 (14)
O1—C2—C3	125.06 (15)	O3—C18—C19	124.44 (15)
O1—C2—C1	115.10 (14)	O3—C18—C17	116.05 (14)
C3—C2—C1	119.84 (15)	C19—C18—C17	119.51 (15)
C4—C3—C2	120.06 (16)	C20—C19—C18	120.20 (16)
C4—C3—H3A	120.0	C20—C19—H19A	119.9
C2—C3—H3A	120.0	C18—C19—H19A	119.9
C5—C4—C3	120.33 (16)	C21—C20—C19	120.42 (16)
C5—C4—H4A	119.8	C21—C20—H20A	119.8
C3—C4—H4A	119.8	C19—C20—H20A	119.8
C4—C5—C6	119.94 (16)	C20—C21—C22	119.60 (16)
C4—C5—H5A	120.0	C20—C21—H21A	120.2
C6—C5—H5A	120.0	C22—C21—H21A	120.2
C5—C6—C1	120.43 (16)	C21—C22—C17	120.93 (16)
C5—C6—H6A	119.8	C21—C22—H22A	119.5
C1—C6—H6A	119.8	C17—C22—H22A	119.5
O1—C7—C8	107.45 (15)	O3—C23—C24	106.93 (14)
O1—C7—H7A	110.2	O3—C23—H23A	110.3
C8—C7—H7A	110.2	C24—C23—H23A	110.3
O1—C7—H7B	110.2	O3—C23—H23B	110.3
C8—C7—H7B	110.2	C24—C23—H23B	110.3
H7A—C7—H7B	108.5	H23A—C23—H23B	108.6
C7—C8—H8A	109.5	C23—C24—H24A	109.5
C7—C8—H8B	109.5	C23—C24—H24B	109.5
H8A—C8—H8B	109.5	H24A—C24—H24B	109.5
C7—C8—H8C	109.5	C23—C24—H24C	109.5
H8A—C8—H8C	109.5	H24A—C24—H24C	109.5
H8B—C8—H8C	109.5	H24B—C24—H24C	109.5
C14—C9—C10	119.11 (14)	C30—C25—N6	123.08 (14)
C14—C9—N3	124.14 (14)	C30—C25—C26	119.77 (14)
C10—C9—N3	116.74 (14)	N6—C25—C26	117.08 (14)
O2—C10—C11	124.14 (15)	O4—C26—C27	124.58 (14)
O2—C10—C9	116.04 (14)	O4—C26—C25	115.80 (14)
C11—C10—C9	119.82 (15)	C27—C26—C25	119.62 (14)
C12—C11—C10	119.79 (15)	C26—C27—C28	119.93 (15)
C12—C11—H11A	120.1	C26—C27—H27A	120.0
C10—C11—H11A	120.1	C28—C27—H27A	120.0
C13—C12—C11	120.73 (16)	C29—C28—C27	120.51 (15)
C13—C12—H12A	119.6	C29—C28—H28A	119.7
C11—C12—H12A	119.6	C27—C28—H28A	119.7
C14—C13—C12	119.60 (16)	C28—C29—C30	119.94 (15)
C14—C13—H13A	120.2	C28—C29—H29A	120.0
C12—C13—H13A	120.2	C30—C29—H29A	120.0
C13—C14—C9	120.92 (15)	C29—C30—C25	120.22 (15)
C13—C14—H14A	119.5	C29—C30—H30A	119.9
C9—C14—H14A	119.5	C25—C30—H30A	119.9
O2—C15—C16	107.22 (15)	O4—C31—C32	107.73 (13)
O2—C15—H15A	110.3	O4—C31—H31A	110.2
C16—C15—H15A	110.3	C32—C31—H31A	110.2
O2—C15—H15B	110.3	O4—C31—H31B	110.2
C16—C15—H15B	110.3	C32—C31—H31B	110.2
H15A—C15—H15B	108.5	H31A—C31—H31B	108.5
C15—C16—H16A	109.5	C31—C32—H32A	109.5
C15—C16—H16B	109.5	C31—C32—H32B	109.5
H16A—C16—H16B	109.5	H32A—C32—H32B	109.5
C15—C16—H16C	109.5	C31—C32—H32C	109.5
H16A—C16—H16C	109.5	H32A—C32—H32C	109.5
H16B—C16—H16C	109.5	H32B—C32—H32C	109.5
C1—N1—N2—N3	−179.87 (14)	C17—N4—N5—N6	176.67 (13)
N1—N2—N3—C9	−179.45 (13)	N4—N5—N6—C25	179.15 (13)
N2—N1—C1—C6	15.8 (2)	N5—N4—C17—C22	−0.5 (2)
N2—N1—C1—C2	−163.08 (14)	N5—N4—C17—C18	−177.30 (14)
C7—O1—C2—C3	−0.5 (2)	C23—O3—C18—C19	−13.0 (2)
C7—O1—C2—C1	179.30 (14)	C23—O3—C18—C17	166.92 (14)
C6—C1—C2—O1	179.75 (14)	C22—C17—C18—O3	178.74 (14)
N1—C1—C2—O1	−1.4 (2)	N4—C17—C18—O3	−4.3 (2)
C6—C1—C2—C3	−0.5 (2)	C22—C17—C18—C19	−1.3 (2)
N1—C1—C2—C3	178.44 (15)	N4—C17—C18—C19	175.66 (14)
O1—C2—C3—C4	180.00 (15)	O3—C18—C19—C20	−178.65 (15)
C1—C2—C3—C4	0.2 (3)	C17—C18—C19—C20	1.4 (2)
C2—C3—C4—C5	0.0 (3)	C18—C19—C20—C21	0.0 (3)
C3—C4—C5—C6	0.1 (3)	C19—C20—C21—C22	−1.6 (3)
C4—C5—C6—C1	−0.3 (3)	C20—C21—C22—C17	1.7 (3)
N1—C1—C6—C5	−178.32 (16)	C18—C17—C22—C21	−0.2 (2)
C2—C1—C6—C5	0.5 (2)	N4—C17—C22—C21	−176.97 (16)
C2—O1—C7—C8	178.55 (14)	C18—O3—C23—C24	−177.46 (14)
N2—N3—C9—C14	−0.7 (2)	N5—N6—C25—C30	3.8 (2)
N2—N3—C9—C10	−179.91 (14)	N5—N6—C25—C26	−173.27 (14)
C15—O2—C10—C11	−12.3 (2)	C31—O4—C26—C27	−2.5 (2)
C15—O2—C10—C9	167.79 (14)	C31—O4—C26—C25	177.30 (13)
C14—C9—C10—O2	−179.35 (14)	C30—C25—C26—O4	179.94 (14)
N3—C9—C10—O2	−0.1 (2)	N6—C25—C26—O4	−2.9 (2)
C14—C9—C10—C11	0.8 (2)	C30—C25—C26—C27	−0.2 (2)
N3—C9—C10—C11	179.99 (15)	N6—C25—C26—C27	176.98 (14)
O2—C10—C11—C12	−179.23 (16)	O4—C26—C27—C28	−179.79 (15)
C9—C10—C11—C12	0.6 (2)	C25—C26—C27—C28	0.4 (2)
C10—C11—C12—C13	−1.1 (3)	C26—C27—C28—C29	−0.2 (2)
C11—C12—C13—C14	0.1 (3)	C27—C28—C29—C30	−0.1 (2)
C12—C13—C14—C9	1.3 (3)	C28—C29—C30—C25	0.3 (2)
C10—C9—C14—C13	−1.8 (2)	N6—C25—C30—C29	−177.13 (15)
N3—C9—C14—C13	179.08 (15)	C26—C25—C30—C29	−0.1 (2)
C10—O2—C15—C16	−175.19 (14)	C26—O4—C31—C32	179.72 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N4	0.91	2.12	3.018 (2)	170
N6—H6N···N3	0.91	2.11	3.008 (2)	170
C4—H4A···Cg1i	0.95	2.85	3.686 (2)	147
C32—H32B···Cg2ii	0.98	2.78	3.549 (3)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N4	0.91	2.12	3.018 (2)	170
N6—H6N⋯N3	0.91	2.11	3.008 (2)	170
C4—H4A⋯Cg1i	0.95	2.85	3.686 (2)	147
C32—H32B⋯Cg2ii	0.98	2.78	3.549 (3)	136

Symmetry codes: (i) ; (ii) . Cg1 and Cg2 are the centroids of the C17–C22 and C25–C30 rings, respectively.