2-Diethyl­amino-3-(3-methyl­phen­yl)-1-benzofuro[3,2-d]pyrimidin-4(3H)-one

Liu, M.-G.; Yuan, J.-Z.; Hu, Y.-G.; Xu, S.-Z.

doi:10.1107/S1600536805040377

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2-Diethylamino-3-(3-methylphenyl)-1-benzofuro[3,2-d]pyrimidin-4(3H)-one

M.-G. Liu, J.-Z. Yuan, Y.-G. Hu and S.-Z. Xu

In the title compound, C₂₁H₂₁N₃O₂, the three fused rings of the 1-benzofuro[3,2-d]pyrimidine system are almost coplanar. The packing of the molecules in the crystal structure is mainly governed by π–π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805040377/sj6175sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805040377/sj6175Isup2.hkl Contains datablock I

CCDC reference: 296663

checkCIF report

Key indicators

Single-crystal X-ray study
T = 292 K
Mean (C-C)= 0.004 Å
R factor = 0.060
wR factor = 0.145
Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Comment top

The derivatives of benzofuropyrimidines are of great importance because of their remarkable biological properties (Bodke & Sangapure, 2003). In recent years, we have been engaged in the preparation of the derivatives of heterocycles via an aza-Wittig reaction (Ding et al., 2004a,b). The heterocyclic title compound, (I), may be used as a new precursor for obtaining bioactive molecules and its structure is presented here (Fig. 1). The three fused rings of the benzofuro[3,2-d]pyrimidine system are almost coplanar, with a maximum deviation of −0.079 (2) Å for C9. This plane is at an angle of 63.79 (11)° to the substituted benzene ring. Bond lengths and angles (Table 1) are in agreement with reported literature values (Allen et al.,1987). [NB: the scheme is for a different compound; please replace]

The centroid-to-centroid distances are 3.5173 (2) for rings A (O1, C1 C6, C7, C8) and Bⁱ (C1, C2, C3, C4, C5, C6) [symmetry code: (i) = 2 − x, 2 − y, 2 − z] and 3.6726 (3) Å for rings B and Aⁱⁱ [symmetry code: (ii) = 2 − x, 1 − y, 2 − z]. The corresponding dihedral angles are 0.03 (2) and 1.26 (2)°, respectively. The contribution of π–π stacking interactions to the stability of the crystal is further demonstrated by the angles between the ring-centroid vectors [7.84 (2) for A to Bⁱ and 20.42 (3)° for B to Aⁱⁱ] and the angles between the ring normals [8.58 (3) and 20.87 (2)° (Janiak, 2000)].

Experimental top

To a solution of iminophosphorane (1.40 g, 3 mmol) in dry dichloromethane (15 ml) was added phenyl isocyanate (3 mmol) under nitrogen at room temperature. After standing for 10 h at 273–278 K, the solvent was removed under reduced pressure and ether/petroleum ether (1:2, 20 ml) was added to precipitate triphenylphosphine oxide. After filtration the solvent was removed to give the carbodiimide, (II), which was used directly without further purification. To the solution of (II) prepared above in dichloromethane (15 ml) was added diethylamine (3 mmol). After the reaction mixture was allowed to stand for 0.5 h, the solvent was removed and anhydrous ethanol (10 ml) and several drops of EtONa in EtOH were added. The mixture was stirred for 3 h at room temperature, concentrated under reduced pressure and the residue recrystallized from ethanol to give the title compound (I) (yield 0.81 g, 78%, m.p. 420 K). Suitable crystals were obtained by vapor diffusion of ethanol and dichloromethane at room temperature. Spectroscopic analysis:¹H NMR (CDCl₃, 400 MHz): 0.84–0.88(t, 6H, CH3, J=7.2 Hz), 2.42 (s, 3H, CH3), 3.12–3.17 (q, 4H, CH2, J = 6.8 Hz), 7.14–8.03 (m, 8H, Ar—H). MS (EI 70 eV) m/z(%): 347 (M⁺, 62), 318 (86), 275 (65), 130 (84), 91 (100). Elemental analysis: calculated for C₂₁H₂₁N₃O₂: C 72.60, H 6.09, N 12.10%; found: C 72.52, H 6.16, N 12.07%.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. View of (I), showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. H-atoms are represented by circles of arbitrary size.
	Fig. 2. Packing diagram for (I), showing the π–π stacking interactions.

2-Diethylamino-3-(3-methylphenyl)-1-benzofuro[3,2-d]pyrimidin-4(3H)-one top

Crystal data top

C₂₁H₂₁N₃O₂	F(000) = 736
M_r = 347.41	D_x = 1.262 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 420 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 16.164 (2) Å	Cell parameters from 1397 reflections
b = 7.0063 (9) Å	θ = 2.5–21.6°
c = 17.627 (2) Å	µ = 0.08 mm⁻¹
β = 113.685 (2)°	T = 292 K
V = 1828.1 (4) Å³	Block, colorless
Z = 4	0.30 × 0.20 × 0.16 mm

Data collection top

Bruker CCD area-detector diffractometer	1941 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.069
Graphite monochromator	θ_max = 26.0°, θ_min = 2.5°
ϕ and ω scans	h = −19→19
11487 measured reflections	k = −8→8
3590 independent reflections	l = −19→21

Refinement top

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.145	H-atom parameters constrained
S = 0.94	w = 1/[σ²(F_o²) + (0.0572P)²] where P = (F_o² + 2F_c²)/3
3590 reflections	(Δ/σ)_max = 0.001
238 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₁H₂₁N₃O₂	V = 1828.1 (4) Å³
M_r = 347.41	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 16.164 (2) Å	µ = 0.08 mm⁻¹
b = 7.0063 (9) Å	T = 292 K
c = 17.627 (2) Å	0.30 × 0.20 × 0.16 mm
β = 113.685 (2)°

Data collection top

Bruker CCD area-detector diffractometer	1941 reflections with I > 2σ(I)
11487 measured reflections	R_int = 0.069
3590 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.145	H-atom parameters constrained
S = 0.94	Δρ_max = 0.20 e Å⁻³
3590 reflections	Δρ_min = −0.16 e Å⁻³
238 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.95360 (17)	0.7410 (3)	0.98052 (16)	0.0438 (6)
C2	0.87591 (18)	0.7069 (4)	0.99426 (19)	0.0570 (8)
H2	0.8197	0.6966	0.9504	0.068*
C3	0.8853 (2)	0.6889 (4)	1.0754 (2)	0.0694 (9)
H3	0.8346	0.6654	1.0865	0.083*
C4	0.9698 (3)	0.7056 (4)	1.1407 (2)	0.0711 (9)
H4	0.9738	0.6945	1.1946	0.085*
C5	1.0471 (2)	0.7376 (4)	1.12877 (18)	0.0586 (8)
H5	1.1032	0.7485	1.1728	0.070*
C6	1.03678 (18)	0.7524 (3)	1.04780 (16)	0.0457 (6)
C7	0.97333 (15)	0.7684 (3)	0.90768 (16)	0.0408 (6)
C8	1.06472 (15)	0.7894 (3)	0.93737 (16)	0.0429 (6)
C9	1.11201 (17)	0.8024 (4)	0.88575 (17)	0.0494 (7)
C10	0.95607 (15)	0.8036 (3)	0.77603 (16)	0.0418 (6)
C11	0.81104 (16)	0.7555 (4)	0.66205 (18)	0.0625 (8)
H11A	0.7780	0.7999	0.6057	0.075*
H11B	0.7832	0.8114	0.6964	0.075*
C12	0.8040 (2)	0.5421 (5)	0.6641 (2)	0.0952 (12)
H12A	0.8283	0.4864	0.6277	0.143*
H12B	0.7417	0.5062	0.6464	0.143*
H12C	0.8374	0.4973	0.7195	0.143*
C13	0.91523 (18)	0.9989 (4)	0.65194 (16)	0.0583 (8)
H13A	0.9735	1.0553	0.6850	0.070*
H13B	0.8688	1.0882	0.6507	0.070*
C14	0.9083 (2)	0.9687 (5)	0.56471 (18)	0.0911 (11)
H14A	0.9580	0.8917	0.5661	0.137*
H14B	0.9100	1.0900	0.5400	0.137*
H14C	0.8525	0.9053	0.5326	0.137*
C15	1.09034 (16)	0.7812 (4)	0.74123 (16)	0.0457 (6)
C16	1.14573 (17)	0.9188 (4)	0.73121 (17)	0.0579 (8)
H16	1.1564	1.0317	0.7614	0.069*
C17	1.18547 (18)	0.8880 (5)	0.67595 (19)	0.0664 (9)
H17	1.2226	0.9808	0.6685	0.080*
C18	1.17019 (19)	0.7215 (5)	0.63244 (19)	0.0667 (9)
H18	1.1977	0.7027	0.5958	0.080*
C19	1.11495 (17)	0.5793 (4)	0.64104 (17)	0.0544 (7)
C20	1.07530 (16)	0.6136 (4)	0.69651 (16)	0.0499 (7)
H20	1.0377	0.5213	0.7037	0.060*
C21	1.0999 (2)	0.3947 (5)	0.5943 (2)	0.0851 (10)
H21A	1.0808	0.4207	0.5363	0.128*
H21B	1.0540	0.3223	0.6031	0.128*
H21C	1.1551	0.3229	0.6137	0.128*
N1	0.91649 (13)	0.7793 (3)	0.82638 (13)	0.0443 (5)
N2	1.04982 (12)	0.8066 (3)	0.80046 (12)	0.0436 (5)
N3	0.90515 (13)	0.8210 (3)	0.69147 (13)	0.0476 (6)
O1	1.10616 (11)	0.7816 (2)	1.02253 (10)	0.0494 (5)
O2	1.19323 (11)	0.8035 (3)	0.90580 (11)	0.0702 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0516 (15)	0.0299 (14)	0.0528 (18)	0.0072 (11)	0.0241 (14)	0.0018 (12)
C2	0.0572 (17)	0.0525 (18)	0.068 (2)	0.0084 (13)	0.0316 (16)	0.0056 (15)
C3	0.089 (2)	0.055 (2)	0.089 (3)	0.0060 (17)	0.062 (2)	0.0077 (18)
C4	0.110 (3)	0.051 (2)	0.064 (2)	0.0071 (18)	0.048 (2)	0.0059 (16)
C5	0.083 (2)	0.0458 (18)	0.0457 (19)	0.0045 (15)	0.0242 (16)	0.0022 (14)
C6	0.0590 (17)	0.0345 (15)	0.0423 (17)	0.0043 (12)	0.0191 (14)	−0.0003 (12)
C7	0.0405 (14)	0.0335 (15)	0.0453 (17)	0.0036 (11)	0.0140 (13)	−0.0007 (12)
C8	0.0400 (14)	0.0449 (16)	0.0363 (16)	0.0022 (11)	0.0076 (12)	−0.0021 (12)
C9	0.0379 (14)	0.0582 (19)	0.0455 (18)	0.0008 (13)	0.0097 (14)	0.0025 (13)
C10	0.0355 (13)	0.0394 (15)	0.0421 (17)	0.0007 (11)	0.0067 (13)	−0.0029 (12)
C11	0.0404 (15)	0.069 (2)	0.056 (2)	−0.0023 (14)	−0.0035 (14)	0.0012 (15)
C12	0.071 (2)	0.069 (2)	0.105 (3)	−0.0172 (18)	−0.007 (2)	0.007 (2)
C13	0.0553 (17)	0.0578 (19)	0.0468 (18)	0.0031 (14)	0.0049 (14)	0.0060 (14)
C14	0.107 (3)	0.104 (3)	0.044 (2)	−0.006 (2)	0.0106 (19)	0.0175 (19)
C15	0.0423 (14)	0.0521 (18)	0.0384 (16)	0.0030 (12)	0.0118 (12)	0.0041 (13)
C16	0.0499 (16)	0.065 (2)	0.056 (2)	−0.0104 (14)	0.0187 (15)	0.0002 (15)
C17	0.0541 (18)	0.080 (2)	0.067 (2)	−0.0060 (16)	0.0263 (16)	0.0140 (18)
C18	0.0565 (18)	0.092 (3)	0.057 (2)	0.0103 (18)	0.0284 (16)	0.0110 (19)
C19	0.0451 (15)	0.067 (2)	0.0501 (18)	0.0096 (14)	0.0176 (14)	0.0012 (15)
C20	0.0423 (15)	0.0549 (19)	0.0500 (18)	0.0047 (13)	0.0159 (14)	0.0074 (14)
C21	0.090 (2)	0.086 (3)	0.085 (3)	0.013 (2)	0.040 (2)	−0.012 (2)
N1	0.0365 (11)	0.0484 (14)	0.0432 (14)	0.0034 (9)	0.0109 (11)	0.0003 (10)
N2	0.0345 (11)	0.0543 (14)	0.0382 (13)	0.0006 (9)	0.0105 (10)	−0.0002 (10)
N3	0.0400 (12)	0.0493 (14)	0.0416 (14)	−0.0010 (10)	0.0038 (11)	0.0029 (11)
O1	0.0493 (10)	0.0553 (12)	0.0365 (11)	0.0003 (8)	0.0098 (9)	−0.0008 (8)
O2	0.0339 (10)	0.1161 (18)	0.0540 (13)	−0.0010 (10)	0.0106 (9)	0.0058 (11)

Geometric parameters (Å, º) top

C1—C2	1.392 (3)	C12—H12A	0.9600
C1—C6	1.393 (3)	C12—H12B	0.9600
C1—C7	1.455 (3)	C12—H12C	0.9600
C2—C3	1.381 (4)	C13—N3	1.469 (3)
C2—H2	0.9300	C13—C14	1.511 (3)
C3—C4	1.394 (4)	C13—H13A	0.9700
C3—H3	0.9300	C13—H13B	0.9700
C4—C5	1.365 (4)	C14—H14A	0.9600
C4—H4	0.9300	C14—H14B	0.9600
C5—C6	1.373 (3)	C14—H14C	0.9600
C5—H5	0.9300	C15—C16	1.374 (3)
C6—O1	1.378 (3)	C15—C20	1.380 (3)
C7—N1	1.359 (3)	C15—N2	1.449 (3)
C7—C8	1.363 (3)	C16—C17	1.382 (4)
C8—O1	1.378 (3)	C16—H16	0.9300
C8—C9	1.407 (3)	C17—C18	1.363 (4)
C9—O2	1.215 (3)	C17—H17	0.9300
C9—N2	1.434 (3)	C18—C19	1.386 (4)
C10—N1	1.297 (3)	C18—H18	0.9300
C10—N3	1.389 (3)	C19—C20	1.388 (3)
C10—N2	1.399 (3)	C19—C21	1.500 (4)
C11—N3	1.470 (3)	C20—H20	0.9300
C11—C12	1.501 (4)	C21—H21A	0.9600
C11—H11A	0.9700	C21—H21B	0.9600
C11—H11B	0.9700	C21—H21C	0.9600

C2—C1—C6	119.5 (2)	N3—C13—H13A	109.0
C2—C1—C7	135.2 (3)	C14—C13—H13A	109.0
C6—C1—C7	105.4 (2)	N3—C13—H13B	109.0
C3—C2—C1	117.7 (3)	C14—C13—H13B	109.0
C3—C2—H2	121.2	H13A—C13—H13B	107.8
C1—C2—H2	121.2	C13—C14—H14A	109.5
C2—C3—C4	120.7 (3)	C13—C14—H14B	109.5
C2—C3—H3	119.6	H14A—C14—H14B	109.5
C4—C3—H3	119.6	C13—C14—H14C	109.5
C5—C4—C3	122.7 (3)	H14A—C14—H14C	109.5
C5—C4—H4	118.7	H14B—C14—H14C	109.5
C3—C4—H4	118.7	C16—C15—C20	119.8 (2)
C4—C5—C6	115.9 (3)	C16—C15—N2	120.8 (2)
C4—C5—H5	122.1	C20—C15—N2	119.3 (2)
C6—C5—H5	122.1	C15—C16—C17	119.5 (3)
C5—C6—O1	124.9 (3)	C15—C16—H16	120.3
C5—C6—C1	123.6 (3)	C17—C16—H16	120.3
O1—C6—C1	111.5 (2)	C18—C17—C16	120.0 (3)
N1—C7—C8	124.6 (2)	C18—C17—H17	120.0
N1—C7—C1	130.0 (2)	C16—C17—H17	120.0
C8—C7—C1	105.3 (2)	C17—C18—C19	122.2 (3)
C7—C8—O1	113.1 (2)	C17—C18—H18	118.9
C7—C8—C9	123.1 (2)	C19—C18—H18	118.9
O1—C8—C9	123.7 (2)	C18—C19—C20	116.9 (3)
O2—C9—C8	128.1 (2)	C18—C19—C21	122.0 (3)
O2—C9—N2	121.7 (2)	C20—C19—C21	121.1 (3)
C8—C9—N2	110.2 (2)	C15—C20—C19	121.6 (3)
N1—C10—N3	120.2 (2)	C15—C20—H20	119.2
N1—C10—N2	124.2 (2)	C19—C20—H20	119.2
N3—C10—N2	115.5 (2)	C19—C21—H21A	109.5
N3—C11—C12	112.4 (2)	C19—C21—H21B	109.5
N3—C11—H11A	109.1	H21A—C21—H21B	109.5
C12—C11—H11A	109.1	C19—C21—H21C	109.5
N3—C11—H11B	109.1	H21A—C21—H21C	109.5
C12—C11—H11B	109.1	H21B—C21—H21C	109.5
H11A—C11—H11B	107.9	C10—N1—C7	114.8 (2)
C11—C12—H12A	109.5	C10—N2—C9	122.6 (2)
C11—C12—H12B	109.5	C10—N2—C15	121.6 (2)
H12A—C12—H12B	109.5	C9—N2—C15	115.05 (18)
C11—C12—H12C	109.5	C10—N3—C13	116.9 (2)
H12A—C12—H12C	109.5	C10—N3—C11	115.8 (2)
H12B—C12—H12C	109.5	C13—N3—C11	113.2 (2)
N3—C13—C14	112.8 (2)	C8—O1—C6	104.81 (19)

C6—C1—C2—C3	1.0 (4)	C18—C19—C20—C15	−0.2 (4)
C7—C1—C2—C3	−179.9 (3)	C21—C19—C20—C15	178.5 (3)
C1—C2—C3—C4	0.3 (4)	N3—C10—N1—C7	−178.6 (2)
C2—C3—C4—C5	−0.9 (5)	N2—C10—N1—C7	4.0 (3)
C3—C4—C5—C6	0.0 (4)	C8—C7—N1—C10	3.0 (3)
C4—C5—C6—O1	−179.0 (2)	C1—C7—N1—C10	−179.6 (2)
C4—C5—C6—C1	1.5 (4)	N1—C10—N2—C9	−6.6 (4)
C2—C1—C6—C5	−2.0 (4)	N3—C10—N2—C9	175.9 (2)
C7—C1—C6—C5	178.7 (2)	N1—C10—N2—C15	162.6 (2)
C2—C1—C6—O1	178.4 (2)	N3—C10—N2—C15	−14.8 (3)
C7—C1—C6—O1	−1.0 (3)	O2—C9—N2—C10	179.4 (2)
C2—C1—C7—N1	4.2 (5)	C8—C9—N2—C10	1.8 (3)
C6—C1—C7—N1	−176.6 (2)	O2—C9—N2—C15	9.5 (4)
C2—C1—C7—C8	−178.0 (3)	C8—C9—N2—C15	−168.1 (2)
C6—C1—C7—C8	1.2 (3)	C16—C15—N2—C10	121.6 (3)
N1—C7—C8—O1	176.9 (2)	C20—C15—N2—C10	−60.6 (3)
C1—C7—C8—O1	−1.0 (3)	C16—C15—N2—C9	−68.4 (3)
N1—C7—C8—C9	−7.9 (4)	C20—C15—N2—C9	109.4 (3)
C1—C7—C8—C9	174.2 (2)	N1—C10—N3—C13	120.2 (3)
C7—C8—C9—O2	−172.5 (3)	N2—C10—N3—C13	−62.2 (3)
O1—C8—C9—O2	2.2 (4)	N1—C10—N3—C11	−17.2 (3)
C7—C8—C9—N2	4.9 (3)	N2—C10—N3—C11	160.4 (2)
O1—C8—C9—N2	179.6 (2)	C14—C13—N3—C10	145.1 (2)
C20—C15—C16—C17	0.4 (4)	C14—C13—N3—C11	−76.5 (3)
N2—C15—C16—C17	178.1 (2)	C12—C11—N3—C10	−71.8 (3)
C15—C16—C17—C18	−0.6 (4)	C12—C11—N3—C13	149.3 (3)
C16—C17—C18—C19	0.4 (5)	C7—C8—O1—C6	0.5 (3)
C17—C18—C19—C20	0.0 (4)	C9—C8—O1—C6	−174.7 (2)
C17—C18—C19—C21	−178.7 (3)	C5—C6—O1—C8	−179.2 (2)
C16—C15—C20—C19	0.0 (4)	C1—C6—O1—C8	0.4 (3)
N2—C15—C20—C19	−177.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···N2	0.97	2.59	2.971 (3)	104

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁N₃O₂
M_r	347.41
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	292
a, b, c (Å)	16.164 (2), 7.0063 (9), 17.627 (2)
β (°)	113.685 (2)
V (Å³)	1828.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.20 × 0.16

Data collection
Diffractometer	Bruker CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11487, 3590, 1941
R_int	0.069
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.145, 0.94
No. of reflections	3590
No. of parameters	238
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.16

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

Selected geometric parameters (Å, º) top

C1—C2	1.392 (3)	C10—N3	1.389 (3)
C1—C6	1.393 (3)	C10—N2	1.399 (3)
C1—C7	1.455 (3)	C11—N3	1.470 (3)
C5—C6	1.373 (3)	C13—N3	1.469 (3)
C6—O1	1.378 (3)	C15—C16	1.374 (3)
C7—N1	1.359 (3)	C15—C20	1.380 (3)
C7—C8	1.363 (3)	C15—N2	1.449 (3)
C8—O1	1.378 (3)	C16—C17	1.382 (4)
C8—C9	1.407 (3)	C17—C18	1.363 (4)
C9—O2	1.215 (3)	C18—C19	1.386 (4)
C9—N2	1.434 (3)	C19—C20	1.388 (3)
C10—N1	1.297 (3)	C19—C21	1.500 (4)

C2—C1—C6	119.5 (2)	C7—C8—C9	123.1 (2)
C2—C1—C7	135.2 (3)	O1—C8—C9	123.7 (2)
C6—C1—C7	105.4 (2)	O2—C9—C8	128.1 (2)
C3—C2—C1	117.7 (3)	O2—C9—N2	121.7 (2)
C2—C3—C4	120.7 (3)	C8—C9—N2	110.2 (2)
C5—C4—C3	122.7 (3)	N1—C10—N3	120.2 (2)
C5—C6—O1	124.9 (3)	N1—C10—N2	124.2 (2)
C5—C6—C1	123.6 (3)	N3—C10—N2	115.5 (2)
O1—C6—C1	111.5 (2)	C16—C15—N2	120.8 (2)
N1—C7—C8	124.6 (2)	C20—C15—N2	119.3 (2)
N1—C7—C1	130.0 (2)	C10—N3—C13	116.9 (2)
C8—C7—C1	105.3 (2)	C10—N3—C11	115.8 (2)
C7—C8—O1	113.1 (2)	C8—O1—C6	104.81 (19)

C6—C1—C2—C3	1.0 (4)	C2—C1—C7—C8	−178.0 (3)
C7—C1—C2—C3	−179.9 (3)	C6—C1—C7—C8	1.2 (3)
C4—C5—C6—O1	−179.0 (2)	C1—C7—C8—O1	−1.0 (3)
C4—C5—C6—C1	1.5 (4)	O1—C8—C9—O2	2.2 (4)
C2—C1—C6—C5	−2.0 (4)	O1—C8—C9—N2	179.6 (2)
C7—C1—C6—C5	178.7 (2)	C1—C7—N1—C10	−179.6 (2)
C2—C1—C6—O1	178.4 (2)	O2—C9—N2—C10	179.4 (2)
C7—C1—C6—O1	−1.0 (3)	C8—C9—N2—C10	1.8 (3)
C6—C1—C7—N1	−176.6 (2)	C8—C9—N2—C15	−168.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···N2	0.97	2.59	2.971 (3)	104

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