5-(4-Methyl­benzo­yl)-4-p-tolyl-1-(1-p-tolyl­ethyl­ideneamino)pyrimidin-2(1H)-one

Dinçer, M.; Özdemir, N.; Önal, Z.; Korkusuz, E.

doi:10.1107/S1600536807059284

5-(4-Methylbenzoyl)-4-p-tolyl-1-(1-p-tolylethylideneamino)pyrimidin-2(1H)-one

M. Dinçer, N. Özdemir, Z. Önal and E. Korkusuz

The title compound, C₂₈H₂₅N₃O₂, contains four rings that are not coplanar. The pyrimidine ring is slightly distorted from planarity, with a maximum deviation of 0.1032 (9) Å, and adopts the half-chair conformation. The molecules are linked to each other by two C—H

O interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807059284/hg2349sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807059284/hg2349Isup2.hkl Contains datablock I

CCDC reference: 673001

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R factor = 0.044
wR factor = 0.127
Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.75 mm
PLAT432_ALERT_2_C Short Inter X...Y Contact  C2     ..  C2      ..       3.14 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

4-Aroyl-5-aryl-2,3-dihydro-2,3-furandiones represent easily accessible building blocks for the synthesis of heterocyclic systems (Altural et al., 1989; Kollenz et al., 1991; Sarıpınar et al., 2000; Hökelek et al., 2002; Yıldırım et al., 2002). In general, pyrimidines have been found much interest for their widespread potential biological activities (Kleemann & Engel, 1982) and medicinal applications, thus their chemistry has been investigated extensively (Brown, 1984, 1985). Some of them are frequently encountered in many drugs used for the treatment of hypothyroidism, hypertension, cancer chemotherapy or HIV infection (Burdge, 2000). Furthermore many condensed heterocyclic systems, especially when linked to a pyrimidine ring, play an important role as analgesic, antipyretic and anti-inflammatory drugs (Vega et al., 1990), and also as herbicides (Chakaravorty et al., 1992), and plant growth regulators (Shishoo & Jain, 1992). In view of these important properties, we have undertaken the X-ray diffraction study of the title compound, (I).

The structure of the title compound, (I), is shown in Fig. 1. The structure of (I) contains one central pyrimidine ring (N1/N3/C2/C4—C6) with a p-tolylethylideneamino group (N11/C11—C19) substituted at N1, an O atom substituted at C2, a p-tolyl group (C41—C47) substituted at C4 and a methylbenzoyl group substituted at C5. The plane of the pyrimidine ring makes dihedral angles of 35.86 (6), 41.57 (4) and 52.18 (4)° with the (C13—C18), (C41—C46) and (C52—C57) phenyl rings, respectively·The pyrimidine ring is not planar with a maximum deviation of -0.1032 (9) Å for atom C2. The interatomic distances and angles show no anomalies.

In the molecular structure, there is a π—π stacking interaction between the (C41—C46) and (C52—C57) phenyl rings with a distance of 3.749 Å between the ring centroids, and a perpendicular distance between the rings of 3.483 Å. In the crystal structure of (I), atom C53 in the molecule at (x, y, z) acts as hydrogen-bond donor to the O2 atom in the molecule at (1 - x, 1 - y, 2 - z), so generating by inversion a dimeric unit characterized by an R₂²(18) motif (Bernstein et al., 1995). The dimers are connected to one another via another C—H···O interactions in which atom C19 in the molecule at (x, y, z) acts as hydrogen-bond donor to the O2 atom in the molecule at (x, y - 1, z), forming one dimensional dimeric chain along the [010] direction.

Related literature top

For related literature, see: Altural et al. (1989); Bernstein et al. (1995); Brown (1984, 1985); Burdge (2000); Chakaravorty et al. (1992); Hökelek et al. (2002); Kleemann & Engel (1982); Kollenz et al. (1991); Sarıpınar et al. (2000); Shishoo & Jain (1992); Vega et al. (1990); Yıldırım et al. (2002); Ziegler et al. (1967).

Experimental top

An equimolar mixture of 4-(4-methylbenzoyl)-5-(4-methylphenyl)furan-2,3-dione (0.50 g), easily obtained from oxalyl dichloride and 4,4'-dimethyldibenzoylmethan, as described by Ziegler et al. (1967), and 4-methylacetophenone semicarbazone (0.34 g) (molar ratio 1:1) were refluxed in 30 ml boiling toluene for 4 h. After evaporation of the solvent, the oily residue was treated with dry diethyl ether to give a yellow precipitate, which was filtered off and recrystallized from ethanol (yield: 0.35 g, 50%; m.p. 488 K). IR (KBr, ν, cm^-1): 3050, 3044, 2920 (aromatic and aliphatic C—H), 1690, 1645 (s, C═O), 1602–1473 (m, C═C and C═N aromatic rings); ¹H NMR (200 MHz, DMSO, p.p.m.): δ 8.47 (s, 1H at C-6), 7.94–7.13 (m, 12H, Ar—H), 2.39, 2.33, 2.31, 2.27 (s, 12H, 4xCH₃). Analysis Calculated for C₂₈H₂₅N₃O₂: C 77.21, H 5.78, N 9.64%; found: C 77.40, H 5.57, N 9.50%.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Figures top

	Fig. 1. An ORTEP-3 (Farrugia, 1997) drawing of (I), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 40% probability level.
	Fig. 2. A projection of the crystal structure of (I) along the a axis. Dashed lines show the C—H···O intermolecular interactions. For the sake of clarity, H atoms have been omitted unless they are involved in hydrogen bonding.

5-(4-Methylbenzoyl)-4-p-tolyl-1-(1-p-tolylethylideneamino)pyrimidin-2(1H)-one top

Crystal data top

C₂₈H₂₅N₃O₂	Z = 2
M_r = 435.51	F(000) = 460
Triclinic, P1	D_x = 1.235 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0337 (6) Å	Cell parameters from 18925 reflections
b = 10.5159 (8) Å	θ = 2.4–27.9°
c = 14.6372 (11) Å	µ = 0.08 mm⁻¹
α = 90.814 (6)°	T = 296 K
β = 103.780 (5)°	Prism, yellow
γ = 102.235 (6)°	0.75 × 0.57 × 0.29 mm
V = 1170.97 (15) Å³

Data collection top

Stoe IPDS2 diffractometer	5518 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	4001 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.059
Detector resolution: 6.67 pixels mm^-1	θ_max = 27.9°, θ_min = 2.4°
ω scans	h = −10→10
Absorption correction: integration X-RED32 (Stoe & Cie, 2002)	k = −13→13
T_min = 0.951, T_max = 0.980	l = −19→19
17054 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.127	w = 1/[σ²(F_o²) + (0.0563P)² + 0.1024P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
5518 reflections	Δρ_max = 0.18 e Å⁻³
303 parameters	Δρ_min = −0.13 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.018 (3)

Crystal data top

C₂₈H₂₅N₃O₂	γ = 102.235 (6)°
M_r = 435.51	V = 1170.97 (15) Å³
Triclinic, P1	Z = 2
a = 8.0337 (6) Å	Mo Kα radiation
b = 10.5159 (8) Å	µ = 0.08 mm⁻¹
c = 14.6372 (11) Å	T = 296 K
α = 90.814 (6)°	0.75 × 0.57 × 0.29 mm
β = 103.780 (5)°

Data collection top

Stoe IPDS2 diffractometer	5518 independent reflections
Absorption correction: integration X-RED32 (Stoe & Cie, 2002)	4001 reflections with I > 2σ(I)
T_min = 0.951, T_max = 0.980	R_int = 0.059
17054 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.05	Δρ_max = 0.18 e Å⁻³
5518 reflections	Δρ_min = −0.13 e Å⁻³
303 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
O2	0.36136 (14)	0.45935 (11)	1.07609 (7)	0.0605 (3)
O5	0.1090 (2)	0.29263 (11)	0.65039 (8)	0.0858 (4)
N1	0.25410 (15)	0.32241 (11)	0.94305 (8)	0.0485 (3)
N3	0.26204 (15)	0.54801 (11)	0.93782 (7)	0.0478 (3)
N11	0.27934 (16)	0.20825 (11)	0.98928 (8)	0.0517 (3)
C2	0.29839 (17)	0.44711 (14)	0.99159 (9)	0.0481 (3)
C4	0.22738 (16)	0.53503 (13)	0.84561 (9)	0.0446 (3)
C5	0.21944 (18)	0.41521 (13)	0.79567 (9)	0.0483 (3)
C6	0.22964 (19)	0.31113 (13)	0.84897 (9)	0.0511 (3)
H6	0.2194	0.2299	0.8196	0.061*
C11	0.19358 (16)	0.17533 (13)	1.05206 (9)	0.0460 (3)
C12	0.0720 (2)	0.24654 (16)	1.08184 (12)	0.0612 (4)
H12A	0.0269	0.2975	1.0318	0.092*
H12B	0.1342	0.3031	1.1369	0.092*
H12C	−0.0237	0.1851	1.0961	0.092*
C13	0.22176 (16)	0.05315 (13)	1.09645 (9)	0.0464 (3)
C14	0.1693 (2)	0.01848 (16)	1.17784 (11)	0.0605 (4)
H14	0.1162	0.0733	1.2060	0.073*
C15	0.1946 (2)	−0.09636 (17)	1.21779 (11)	0.0679 (4)
H15	0.1600	−0.1167	1.2731	0.081*
C16	0.2702 (2)	−0.18145 (15)	1.17752 (11)	0.0599 (4)
C17	0.3223 (2)	−0.14700 (15)	1.09630 (11)	0.0602 (4)
H17	0.3739	−0.2026	1.0679	0.072*
C18	0.2995 (2)	−0.03240 (15)	1.05655 (10)	0.0555 (3)
H18	0.3367	−0.0116	1.0020	0.067*
C19	0.2925 (3)	−0.30805 (19)	1.21997 (15)	0.0899 (6)
H19A	0.2090	−0.3333	1.2572	0.135*
H19B	0.4095	−0.2972	1.2593	0.135*
H19C	0.2735	−0.3744	1.1705	0.135*
C41	0.19553 (16)	0.65154 (12)	0.79447 (9)	0.0440 (3)
C42	0.30585 (18)	0.77205 (14)	0.82568 (10)	0.0509 (3)
H42	0.3928	0.7808	0.8816	0.061*
C43	0.2875 (2)	0.87876 (15)	0.77436 (11)	0.0609 (4)
H43	0.3638	0.9588	0.7956	0.073*
C44	0.1573 (2)	0.86939 (16)	0.69154 (11)	0.0630 (4)
C45	0.0431 (2)	0.74996 (16)	0.66348 (11)	0.0624 (4)
H45	−0.0480	0.7423	0.6094	0.075*
C46	0.06107 (19)	0.64227 (15)	0.71359 (10)	0.0544 (3)
H46	−0.0173	0.5628	0.6932	0.065*
C47	0.1430 (4)	0.9854 (2)	0.63299 (17)	0.1050 (8)
H47A	0.1624	0.9671	0.5724	0.158*
H47B	0.2296	1.0603	0.6644	0.158*
H47C	0.0278	1.0025	0.6249	0.158*
C51	0.2031 (2)	0.39281 (14)	0.69258 (10)	0.0561 (4)
C52	0.3062 (2)	0.49146 (14)	0.64407 (9)	0.0517 (3)
C53	0.4596 (2)	0.57584 (16)	0.69096 (10)	0.0582 (4)
H53	0.5064	0.5687	0.7547	0.070*
C54	0.5438 (2)	0.67092 (18)	0.64341 (11)	0.0679 (4)
H54	0.6482	0.7268	0.6756	0.081*
C55	0.4767 (2)	0.68502 (18)	0.54924 (12)	0.0698 (4)
C56	0.3253 (3)	0.59822 (19)	0.50232 (11)	0.0762 (5)
H56	0.2794	0.6052	0.4384	0.091*
C57	0.2411 (2)	0.50158 (17)	0.54816 (10)	0.0661 (4)
H57	0.1403	0.4428	0.5150	0.079*
C58	0.5664 (3)	0.7934 (2)	0.49902 (17)	0.1040 (7)
H58A	0.6373	0.8624	0.5443	0.156*
H58B	0.4792	0.8265	0.4550	0.156*
H58C	0.6395	0.7602	0.4659	0.156*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0677 (6)	0.0647 (7)	0.0429 (5)	0.0096 (5)	0.0062 (4)	0.0063 (4)
O5	0.1368 (12)	0.0523 (7)	0.0549 (6)	−0.0028 (7)	0.0193 (7)	−0.0048 (5)
N1	0.0577 (6)	0.0464 (6)	0.0450 (6)	0.0151 (5)	0.0156 (5)	0.0111 (5)
N3	0.0536 (6)	0.0450 (6)	0.0444 (6)	0.0104 (5)	0.0119 (5)	0.0043 (4)
N11	0.0622 (7)	0.0493 (7)	0.0496 (6)	0.0184 (5)	0.0197 (5)	0.0149 (5)
C2	0.0483 (7)	0.0513 (8)	0.0447 (7)	0.0093 (6)	0.0129 (5)	0.0051 (6)
C4	0.0435 (6)	0.0440 (7)	0.0457 (6)	0.0082 (5)	0.0113 (5)	0.0049 (5)
C5	0.0573 (8)	0.0446 (7)	0.0438 (6)	0.0124 (6)	0.0131 (6)	0.0069 (5)
C6	0.0638 (8)	0.0452 (8)	0.0461 (7)	0.0133 (6)	0.0155 (6)	0.0039 (6)
C11	0.0437 (6)	0.0490 (7)	0.0437 (6)	0.0074 (5)	0.0102 (5)	0.0055 (5)
C12	0.0541 (8)	0.0634 (9)	0.0752 (10)	0.0186 (7)	0.0278 (7)	0.0163 (8)
C13	0.0461 (7)	0.0478 (7)	0.0442 (6)	0.0062 (6)	0.0126 (5)	0.0069 (5)
C14	0.0769 (10)	0.0570 (9)	0.0570 (8)	0.0179 (7)	0.0314 (7)	0.0120 (7)
C15	0.0916 (12)	0.0647 (10)	0.0566 (8)	0.0180 (9)	0.0348 (8)	0.0197 (7)
C16	0.0709 (9)	0.0518 (8)	0.0544 (8)	0.0112 (7)	0.0120 (7)	0.0116 (6)
C17	0.0736 (10)	0.0563 (9)	0.0567 (8)	0.0218 (7)	0.0209 (7)	0.0077 (7)
C18	0.0651 (9)	0.0570 (9)	0.0495 (7)	0.0154 (7)	0.0217 (6)	0.0100 (6)
C19	0.1304 (18)	0.0670 (12)	0.0829 (13)	0.0356 (12)	0.0336 (12)	0.0292 (10)
C41	0.0472 (7)	0.0426 (7)	0.0446 (6)	0.0122 (5)	0.0140 (5)	0.0044 (5)
C42	0.0514 (7)	0.0489 (8)	0.0505 (7)	0.0080 (6)	0.0113 (6)	0.0039 (6)
C43	0.0679 (9)	0.0448 (8)	0.0688 (9)	0.0062 (7)	0.0201 (7)	0.0082 (7)
C44	0.0821 (11)	0.0539 (9)	0.0612 (9)	0.0259 (8)	0.0228 (8)	0.0166 (7)
C45	0.0720 (10)	0.0600 (10)	0.0536 (8)	0.0256 (8)	0.0021 (7)	0.0065 (7)
C46	0.0554 (8)	0.0494 (8)	0.0548 (8)	0.0133 (6)	0.0055 (6)	0.0023 (6)
C47	0.152 (2)	0.0719 (13)	0.0965 (15)	0.0379 (14)	0.0266 (15)	0.0392 (12)
C51	0.0787 (10)	0.0454 (8)	0.0450 (7)	0.0182 (7)	0.0127 (7)	0.0044 (6)
C52	0.0691 (9)	0.0507 (8)	0.0393 (6)	0.0216 (7)	0.0137 (6)	0.0052 (5)
C53	0.0596 (8)	0.0765 (10)	0.0418 (7)	0.0217 (7)	0.0125 (6)	0.0102 (7)
C54	0.0619 (9)	0.0845 (12)	0.0567 (9)	0.0100 (8)	0.0189 (7)	0.0079 (8)
C55	0.0836 (11)	0.0732 (11)	0.0582 (9)	0.0176 (9)	0.0275 (8)	0.0168 (8)
C56	0.0997 (13)	0.0848 (12)	0.0402 (7)	0.0163 (11)	0.0125 (8)	0.0165 (8)
C57	0.0854 (11)	0.0652 (10)	0.0409 (7)	0.0101 (8)	0.0081 (7)	0.0036 (7)
C58	0.1195 (18)	0.1058 (18)	0.0881 (14)	0.0085 (14)	0.0414 (13)	0.0367 (13)

Geometric parameters (Å, º) top

O2—C2	1.2133 (16)	C19—H19C	0.9600
O5—C51	1.2185 (19)	C41—C42	1.3837 (19)
N1—C6	1.3437 (16)	C41—C46	1.3859 (19)
N1—N11	1.4146 (15)	C42—C43	1.374 (2)
N1—C2	1.4165 (18)	C42—H42	0.9300
N3—C4	1.3105 (16)	C43—C44	1.386 (2)
N3—C2	1.3696 (17)	C43—H43	0.9300
N11—C11	1.2840 (16)	C44—C45	1.380 (2)
C4—C5	1.4295 (18)	C44—C47	1.509 (2)
C4—C41	1.4815 (17)	C45—C46	1.373 (2)
C5—C6	1.3583 (18)	C45—H45	0.9300
C5—C51	1.4941 (18)	C46—H46	0.9300
C6—H6	0.9300	C47—H47A	0.9600
C11—C13	1.4836 (18)	C47—H47B	0.9600
C11—C12	1.4863 (19)	C47—H47C	0.9600
C12—H12A	0.9600	C51—C52	1.484 (2)
C12—H12B	0.9600	C52—C53	1.376 (2)
C12—H12C	0.9600	C52—C57	1.3907 (19)
C13—C14	1.3844 (18)	C53—C54	1.378 (2)
C13—C18	1.392 (2)	C53—H53	0.9300
C14—C15	1.382 (2)	C54—C55	1.378 (2)
C14—H14	0.9300	C54—H54	0.9300
C15—C16	1.379 (2)	C55—C56	1.377 (3)
C15—H15	0.9300	C55—C58	1.512 (2)
C16—C17	1.380 (2)	C56—C57	1.373 (2)
C16—C19	1.504 (2)	C56—H56	0.9300
C17—C18	1.374 (2)	C57—H57	0.9300
C17—H17	0.9300	C58—H58A	0.9600
C18—H18	0.9300	C58—H58B	0.9600
C19—H19A	0.9600	C58—H58C	0.9600
C19—H19B	0.9600

C6—N1—N11	114.84 (11)	C42—C41—C4	119.64 (12)
C6—N1—C2	120.41 (11)	C46—C41—C4	121.51 (12)
N11—N1—C2	122.59 (11)	C43—C42—C41	120.26 (13)
C4—N3—C2	121.04 (11)	C43—C42—H42	119.9
C11—N11—N1	116.95 (11)	C41—C42—H42	119.9
O2—C2—N3	123.89 (13)	C42—C43—C44	121.28 (15)
O2—C2—N1	120.12 (12)	C42—C43—H43	119.4
N3—C2—N1	115.97 (11)	C44—C43—H43	119.4
N3—C4—C5	122.47 (12)	C45—C44—C43	117.86 (14)
N3—C4—C41	116.60 (11)	C45—C44—C47	121.05 (17)
C5—C4—C41	120.93 (11)	C43—C44—C47	121.08 (17)
C6—C5—C4	115.61 (12)	C46—C45—C44	121.42 (14)
C6—C5—C51	117.06 (12)	C46—C45—H45	119.3
C4—C5—C51	127.32 (12)	C44—C45—H45	119.3
N1—C6—C5	121.76 (12)	C45—C46—C41	120.26 (14)
N1—C6—H6	119.1	C45—C46—H46	119.9
C5—C6—H6	119.1	C41—C46—H46	119.9
N11—C11—C13	114.57 (11)	C44—C47—H47A	109.5
N11—C11—C12	126.30 (13)	C44—C47—H47B	109.5
C13—C11—C12	119.13 (11)	H47A—C47—H47B	109.5
C11—C12—H12A	109.5	C44—C47—H47C	109.5
C11—C12—H12B	109.5	H47A—C47—H47C	109.5
H12A—C12—H12B	109.5	H47B—C47—H47C	109.5
C11—C12—H12C	109.5	O5—C51—C52	121.22 (13)
H12A—C12—H12C	109.5	O5—C51—C5	119.49 (13)
H12B—C12—H12C	109.5	C52—C51—C5	119.26 (13)
C14—C13—C18	117.41 (13)	C53—C52—C57	119.04 (14)
C14—C13—C11	121.58 (12)	C53—C52—C51	122.56 (12)
C18—C13—C11	121.00 (11)	C57—C52—C51	118.35 (14)
C15—C14—C13	120.92 (14)	C52—C53—C54	119.99 (14)
C15—C14—H14	119.5	C52—C53—H53	120.0
C13—C14—H14	119.5	C54—C53—H53	120.0
C16—C15—C14	121.47 (13)	C55—C54—C53	121.40 (17)
C16—C15—H15	119.3	C55—C54—H54	119.3
C14—C15—H15	119.3	C53—C54—H54	119.3
C15—C16—C17	117.60 (14)	C56—C55—C54	118.22 (15)
C15—C16—C19	121.10 (15)	C56—C55—C58	120.97 (17)
C17—C16—C19	121.30 (15)	C54—C55—C58	120.81 (19)
C18—C17—C16	121.42 (14)	C57—C56—C55	121.18 (15)
C18—C17—H17	119.3	C57—C56—H56	119.4
C16—C17—H17	119.3	C55—C56—H56	119.4
C17—C18—C13	121.17 (13)	C56—C57—C52	120.10 (16)
C17—C18—H18	119.4	C56—C57—H57	120.0
C13—C18—H18	119.4	C52—C57—H57	120.0
C16—C19—H19A	109.5	C55—C58—H58A	109.5
C16—C19—H19B	109.5	C55—C58—H58B	109.5
H19A—C19—H19B	109.5	H58A—C58—H58B	109.5
C16—C19—H19C	109.5	C55—C58—H58C	109.5
H19A—C19—H19C	109.5	H58A—C58—H58C	109.5
H19B—C19—H19C	109.5	H58B—C58—H58C	109.5
C42—C41—C46	118.80 (12)

C6—N1—N11—C11	−134.63 (13)	C11—C13—C18—C17	−178.55 (13)
C2—N1—N11—C11	62.05 (17)	N3—C4—C41—C42	44.96 (17)
C4—N3—C2—O2	166.33 (13)	C5—C4—C41—C42	−135.29 (14)
C4—N3—C2—N1	−15.11 (18)	N3—C4—C41—C46	−137.44 (13)
C6—N1—C2—O2	−162.09 (13)	C5—C4—C41—C46	42.31 (18)
N11—N1—C2—O2	0.33 (19)	C46—C41—C42—C43	−3.4 (2)
C6—N1—C2—N3	19.29 (18)	C4—C41—C42—C43	174.26 (12)
N11—N1—C2—N3	−178.29 (11)	C41—C42—C43—C44	1.1 (2)
C2—N3—C4—C5	2.15 (19)	C42—C43—C44—C45	1.8 (2)
C2—N3—C4—C41	−178.09 (11)	C42—C43—C44—C47	−177.08 (17)
N3—C4—C5—C6	7.43 (19)	C43—C44—C45—C46	−2.5 (2)
C41—C4—C5—C6	−172.32 (12)	C47—C44—C45—C46	176.43 (17)
N3—C4—C5—C51	−171.91 (14)	C44—C45—C46—C41	0.2 (2)
C41—C4—C5—C51	8.3 (2)	C42—C41—C46—C45	2.8 (2)
N11—N1—C6—C5	−173.97 (12)	C4—C41—C46—C45	−174.85 (13)
C2—N1—C6—C5	−10.3 (2)	C6—C5—C51—O5	40.4 (2)
C4—C5—C6—N1	−3.1 (2)	C4—C5—C51—O5	−140.30 (16)
C51—C5—C6—N1	176.34 (13)	C6—C5—C51—C52	−137.87 (14)
N1—N11—C11—C13	178.54 (11)	C4—C5—C51—C52	41.5 (2)
N1—N11—C11—C12	−0.9 (2)	O5—C51—C52—C53	−153.66 (16)
N11—C11—C13—C14	166.44 (14)	C5—C51—C52—C53	24.5 (2)
C12—C11—C13—C14	−14.1 (2)	O5—C51—C52—C57	28.7 (2)
N11—C11—C13—C18	−14.75 (19)	C5—C51—C52—C57	−153.05 (14)
C12—C11—C13—C18	164.70 (14)	C57—C52—C53—C54	1.7 (2)
C18—C13—C14—C15	0.4 (2)	C51—C52—C53—C54	−175.85 (14)
C11—C13—C14—C15	179.27 (15)	C52—C53—C54—C55	0.8 (3)
C13—C14—C15—C16	−1.1 (3)	C53—C54—C55—C56	−2.3 (3)
C14—C15—C16—C17	0.9 (3)	C53—C54—C55—C58	177.37 (19)
C14—C15—C16—C19	−178.23 (18)	C54—C55—C56—C57	1.3 (3)
C15—C16—C17—C18	−0.2 (2)	C58—C55—C56—C57	−178.4 (2)
C19—C16—C17—C18	178.96 (17)	C55—C56—C57—C52	1.3 (3)
C16—C17—C18—C13	−0.4 (2)	C53—C52—C57—C56	−2.8 (3)
C14—C13—C18—C17	0.3 (2)	C51—C52—C57—C56	174.93 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C53—H53···O2ⁱ	0.93	2.50	3.4289 (17)	177
C19—H19C···O2ⁱⁱ	0.96	2.53	3.421 (2)	155

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

Experimental details

Crystal data
Chemical formula	C₂₈H₂₅N₃O₂
M_r	435.51
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.0337 (6), 10.5159 (8), 14.6372 (11)
α, β, γ (°)	90.814 (6), 103.780 (5), 102.235 (6)
V (Å³)	1170.97 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.75 × 0.57 × 0.29

Data collection
Diffractometer	Stoe IPDS2 diffractometer
Absorption correction	Integration X-RED32 (Stoe & Cie, 2002)
T_min, T_max	0.951, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	17054, 5518, 4001
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.127, 1.05
No. of reflections	5518
No. of parameters	303
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.13

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2003).