tert-Butyl N-{4-methyl-3-[4-(3-pyrid­yl)pyrimidin-2-yl­oxy]phen­yl}carbamate

Tang, S.-G.; Wang, J.-Q.; Guo, C.

doi:10.1107/S1600536809025604

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1849

doi:10.1107/S1600536809025604

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tert-Butyl N-{4-methyl-3-[4-(3-pyridyl)pyrimidin-2-yloxy]phenyl}carbamate

Shi-Gui Tang,^a Jian-Qiang Wang ^a and Cheng Guo ^a ^*

^aCollege of Science, Nanjing University of Technolgy, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: guocheng@njut.edu.cn

(Received 26 June 2009; accepted 1 July 2009; online 11 July 2009)

In the molecule of the title compound, C₂₁H₂₂N₄O₃, the pyrimidine ring is oriented at dihedral angles of 0.51 (3) and 50.76 (3)° to the pyridine and benzene rings, respectively. In the crystal structure, intermolecular N—H⋯N hydrogen bonds link the molecules into centrosymmetric dimers, forming R₂²(24) ring motifs; the dimers are linked by intermolecular C—H⋯O hydrogen bonds into a two-dimensional network. π–π contacts between the benzene rings and between the pyrimidine and pyridine rings [centroid–centroid distances = 3.891 (1) and 3.646 (1) Å, respectively] may further stabilize the structure. Two weak C—H⋯π interactions are also present.

Related literature

For bond-length data, see: Allen et al. (1987 ). For ring-motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₁H₂₂N₄O₃
M_r = 378.43
Triclinic, $[P \overline 1]$
a = 9.951 (2) Å
b = 10.733 (2) Å
c = 11.577 (2) Å
α = 114.74 (3)°
β = 107.14 (3)°
γ = 99.97 (3)°
V = 1008.6 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 294 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.975, T_max = 0.992
3882 measured reflections
3652 independent reflections
2333 reflections with I > 2σ(I)
R_int = 0.026
3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.184
S = 1.01
3652 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N4ⁱ	0.86	2.10	2.944 (4)	165
C15—H15A⋯O2ⁱⁱ	0.93	2.45	3.382 (4)	177
C18—H18A⋯O2ⁱⁱ	0.93	2.39	3.319 (4)	174
C3—H3B⋯Cg1ⁱ	0.96	2.86	3.560 (3)	131
C12—H12B⋯Cg2ⁱⁱⁱ	0.96	2.90	3.788 (3)	154
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x, -y+1, -z+1; (iii) -x+1, -y+2, -z+2. Cg1 and Cg2 are the centroids of the C6–C11 and N2/N3/C13–C16 rings, respectively.

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809025604/hk2725sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809025604/hk2725Isup2.hkl

checkCIF report

Comment top

Some derivatives of phenol are important chemical materials. We report herein the crystal structure of the title compound.

In the molecule of the title compound (Fig 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C6-C11), B (N2/N3/C13-C16) and C (N4/C17-C21) are, of course, planar and the dihedral angles between them are A/B = 50.76 (3), A/C = 50.58 (3) and B/C = 0.51 (3) °.

In the crystal structure, intermolecular N-H···N hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers forming R₂²(24) ring motifs (Bernstein et al., 1995), and then intermolecular C-H···O hydrogen bonds (Table 1) link them into a two dimensional network (Fig. 2), in which they may be effective in the stabilization of the structure. The π–π contacts between the phenyl rings and between the pyrimidine and the pyridine rings, Cg1—Cg1ⁱ and Cg2—Cg3ⁱⁱ [symmetry codes: (i) 1 - x, 2 - y, 1 - z, (ii) -x, 1 - y, 1 - z, where Cg1, Cg2 and Cg3 are centroids of the rings A (C6-C11), B (N2/N3/C13-C16) and C (N4/C17-C21), respectively] may further stabilize the structure, with centroid-centroid distances of 3.891 (1) and 3.646 (1) Å, respectively. There also exist two weak C—H···π interactions (Table 1).

Related literature top

For bond-length data, see: Allen et al. (1987). For ring-motifs, see: Bernstein et al. (1995). Cg1 and Cg2 are centroids of the C6–C11 and N2/N3/C13–C16 rings, respectively.

Experimental top

To a mixture of 2-(methylsulfonyl)-4-(pyridin-3-yl)pyrimidine (47.1 g, 0.2 mol) in DMF (75 ml) and tert-butyl-3-hydroxy-4-methylphenylcarbamate (44.7 g, 0.2 mol) in DMF (150 ml) was added sodium hydride (44.4 g) slowly and was stirred for 18 h at room temperature. After acidified with citric acid the reaction mixture was poured into ice-water (2000 ml). The precipitate was filtered, washed with water and was extracted with dichloromethane.The dichloromethane layer was dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was recrystallized from ethyl ether to give the title compound (yield; 73.4 g). Crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

tert-Butyl N-{4-methyl-3-[4-(3-pyridyl)pyrimidin-2- yloxy]phenyl}carbamate top

Crystal data top

C₂₁H₂₂N₄O₃	Z = 2
M_r = 378.43	F(000) = 400
Triclinic, P1	D_x = 1.246 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.951 (2) Å	Cell parameters from 25 reflections
b = 10.733 (2) Å	θ = 9–13°
c = 11.577 (2) Å	µ = 0.09 mm⁻¹
α = 114.74 (3)°	T = 294 K
β = 107.14 (3)°	Block, colorless
γ = 99.97 (3)°	0.30 × 0.20 × 0.10 mm
V = 1008.6 (6) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	2333 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.026
Graphite monochromator	θ_max = 25.3°, θ_min = 2.1°
ω/2θ scans	h = 0→11
Absorption correction: ψ scan (North et al., 1968)	k = −12→12
T_min = 0.975, T_max = 0.992	l = −13→13
3882 measured reflections	3 standard reflections every 120 min
3652 independent reflections	intensity decay: 1%

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)] = 0.058	H-atom parameters constrained
wR(F²) = 0.184	w = 1/[σ²(F_o²) + (0.1P)² + 0.07P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
3652 reflections	Δρ_max = 0.29 e Å⁻³
254 parameters	Δρ_min = −0.27 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.033 (5)

Crystal data top

C₂₁H₂₂N₄O₃	γ = 99.97 (3)°
M_r = 378.43	V = 1008.6 (6) Å³
Triclinic, P1	Z = 2
a = 9.951 (2) Å	Mo Kα radiation
b = 10.733 (2) Å	µ = 0.09 mm⁻¹
c = 11.577 (2) Å	T = 294 K
α = 114.74 (3)°	0.30 × 0.20 × 0.10 mm
β = 107.14 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2333 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.026
T_min = 0.975, T_max = 0.992	3 standard reflections every 120 min
3882 measured reflections	intensity decay: 1%
3652 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.184	H-atom parameters constrained
S = 1.01	Δρ_max = 0.29 e Å⁻³
3652 reflections	Δρ_min = −0.27 e Å⁻³
254 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
O1	0.0153 (2)	0.8866 (2)	0.2102 (2)	0.0600 (6)
O2	0.0613 (2)	0.7528 (2)	0.3167 (2)	0.0719 (7)
O3	0.4840 (2)	0.8449 (2)	0.7311 (2)	0.0594 (6)
N1	0.2087 (2)	0.9880 (2)	0.4085 (2)	0.0498 (6)
H1A	0.2141	1.0599	0.3929	0.060*
N2	0.2426 (2)	0.7463 (2)	0.7031 (2)	0.0429 (5)
N3	0.4351 (3)	0.6437 (3)	0.7463 (3)	0.0574 (7)
N4	−0.1874 (3)	0.7568 (2)	0.6228 (3)	0.0567 (7)
C1	−0.1644 (4)	0.8538 (4)	0.0096 (4)	0.0910 (12)
H1B	−0.1731	0.9458	0.0640	0.136*
H1C	−0.2570	0.7920	−0.0708	0.136*
H1D	−0.0855	0.8694	−0.0200	0.136*
C2	−0.1138 (4)	0.6358 (4)	0.0150 (4)	0.0862 (11)
H2B	−0.0922	0.5919	0.0724	0.129*
H2C	−0.0339	0.6503	−0.0136	0.129*
H2D	−0.2057	0.5727	−0.0659	0.129*
C3	−0.2421 (4)	0.7685 (5)	0.1575 (4)	0.0929 (12)
H3B	−0.2485	0.8630	0.2080	0.139*
H3C	−0.2119	0.7312	0.2196	0.139*
H3D	−0.3381	0.7032	0.0834	0.139*
C4	−0.1288 (3)	0.7813 (3)	0.0971 (3)	0.0550 (8)
C5	0.0919 (3)	0.8649 (3)	0.3128 (3)	0.0490 (7)
C6	0.3229 (3)	1.0147 (3)	0.5304 (3)	0.0417 (6)
C7	0.4275 (3)	1.1551 (3)	0.6155 (3)	0.0515 (7)
H7A	0.4202	1.2258	0.5898	0.062*
C8	0.5415 (3)	1.1899 (3)	0.7372 (3)	0.0573 (8)
H8A	0.6102	1.2844	0.7926	0.069*
C9	0.5577 (3)	1.0880 (3)	0.7807 (3)	0.0505 (7)
C10	0.4535 (3)	0.9502 (3)	0.6937 (3)	0.0449 (6)
C11	0.3367 (3)	0.9096 (3)	0.5703 (3)	0.0459 (7)
H11A	0.2689	0.8147	0.5150	0.055*
C12	0.6828 (4)	1.1258 (4)	0.9146 (3)	0.0766 (10)
H12A	0.6742	1.0413	0.9256	0.115*
H12B	0.6764	1.2028	0.9920	0.115*
H12C	0.7773	1.1573	0.9114	0.115*
C13	0.3789 (3)	0.7420 (3)	0.7256 (3)	0.0446 (6)
C14	0.3369 (3)	0.5396 (3)	0.7410 (3)	0.0610 (8)
H14A	0.3692	0.4692	0.7562	0.073*
C15	0.1907 (3)	0.5281 (3)	0.7147 (3)	0.0569 (8)
H15A	0.1244	0.4510	0.7090	0.068*
C16	0.1453 (3)	0.6373 (3)	0.6967 (2)	0.0404 (6)
C17	−0.0094 (3)	0.6389 (3)	0.6684 (3)	0.0404 (6)
C18	−0.1188 (3)	0.5330 (3)	0.6602 (3)	0.0507 (7)
H18A	−0.0970	0.4574	0.6725	0.061*
C19	−0.2597 (3)	0.5405 (3)	0.6339 (3)	0.0571 (8)
H19A	−0.3347	0.4697	0.6277	0.068*
C20	−0.2896 (3)	0.6538 (3)	0.6167 (3)	0.0525 (7)
H20A	−0.3854	0.6584	0.6000	0.063*
C21	−0.0505 (3)	0.7479 (3)	0.6477 (3)	0.0519 (7)
H21A	0.0217	0.8189	0.6514	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0613 (12)	0.0482 (11)	0.0602 (12)	0.0112 (10)	0.0039 (10)	0.0353 (10)
O2	0.0703 (14)	0.0469 (12)	0.0834 (15)	0.0087 (10)	0.0013 (12)	0.0443 (11)
O3	0.0419 (11)	0.0666 (13)	0.0880 (15)	0.0232 (10)	0.0201 (10)	0.0567 (12)
N1	0.0556 (14)	0.0365 (12)	0.0589 (14)	0.0166 (11)	0.0147 (12)	0.0307 (11)
N2	0.0440 (13)	0.0406 (12)	0.0466 (13)	0.0166 (10)	0.0146 (10)	0.0258 (10)
N3	0.0573 (15)	0.0581 (15)	0.0733 (17)	0.0319 (13)	0.0248 (13)	0.0435 (14)
N4	0.0489 (14)	0.0506 (14)	0.0806 (18)	0.0231 (12)	0.0241 (13)	0.0406 (14)
C1	0.089 (3)	0.086 (3)	0.079 (2)	0.018 (2)	0.000 (2)	0.053 (2)
C2	0.101 (3)	0.064 (2)	0.071 (2)	0.030 (2)	0.023 (2)	0.0216 (19)
C3	0.068 (2)	0.119 (3)	0.106 (3)	0.039 (2)	0.037 (2)	0.066 (3)
C4	0.0508 (17)	0.0516 (17)	0.0580 (18)	0.0161 (14)	0.0135 (15)	0.0299 (15)
C5	0.0509 (16)	0.0428 (15)	0.0578 (17)	0.0181 (13)	0.0175 (14)	0.0313 (14)
C6	0.0423 (14)	0.0407 (14)	0.0512 (16)	0.0192 (12)	0.0210 (13)	0.0275 (13)
C7	0.0546 (17)	0.0417 (15)	0.0616 (18)	0.0178 (13)	0.0215 (15)	0.0296 (14)
C8	0.0544 (17)	0.0427 (16)	0.0601 (18)	0.0088 (13)	0.0149 (15)	0.0219 (14)
C9	0.0457 (15)	0.0533 (17)	0.0540 (17)	0.0176 (14)	0.0182 (13)	0.0293 (14)
C10	0.0398 (14)	0.0521 (16)	0.0591 (17)	0.0218 (13)	0.0230 (13)	0.0375 (14)
C11	0.0455 (15)	0.0396 (14)	0.0556 (17)	0.0150 (12)	0.0194 (13)	0.0271 (13)
C12	0.066 (2)	0.079 (2)	0.065 (2)	0.0115 (18)	0.0066 (17)	0.0370 (19)
C13	0.0442 (15)	0.0469 (15)	0.0458 (15)	0.0180 (12)	0.0138 (12)	0.0278 (13)
C14	0.064 (2)	0.0559 (18)	0.086 (2)	0.0355 (16)	0.0306 (17)	0.0495 (18)
C15	0.0608 (19)	0.0468 (16)	0.078 (2)	0.0229 (14)	0.0281 (16)	0.0424 (16)
C16	0.0502 (15)	0.0341 (13)	0.0380 (14)	0.0169 (12)	0.0157 (12)	0.0193 (11)
C17	0.0445 (15)	0.0343 (13)	0.0423 (14)	0.0150 (11)	0.0142 (12)	0.0210 (11)
C18	0.0527 (17)	0.0448 (15)	0.0610 (18)	0.0179 (13)	0.0187 (14)	0.0343 (14)
C19	0.0512 (17)	0.0516 (17)	0.072 (2)	0.0109 (14)	0.0213 (15)	0.0392 (16)
C20	0.0439 (15)	0.0542 (17)	0.0623 (18)	0.0186 (13)	0.0200 (14)	0.0321 (15)
C21	0.0466 (16)	0.0412 (15)	0.073 (2)	0.0157 (12)	0.0196 (14)	0.0363 (15)

Geometric parameters (Å, º) top

O1—C4	1.463 (3)	C6—C7	1.391 (4)
O1—C5	1.344 (3)	C6—C11	1.399 (3)
O2—C5	1.211 (3)	C7—C8	1.373 (4)
O3—C10	1.418 (3)	C7—H7A	0.9300
O3—C13	1.349 (3)	C8—C9	1.396 (4)
N1—C5	1.345 (3)	C8—H8A	0.9300
N1—C6	1.403 (3)	C9—C10	1.372 (4)
N1—H1A	0.8600	C9—C12	1.509 (4)
N3—C13	1.349 (3)	C10—C11	1.380 (4)
N3—C14	1.318 (4)	C11—H11A	0.9300
N4—C20	1.327 (3)	C12—H12A	0.9600
N4—C21	1.336 (3)	C12—H12B	0.9600
C1—C4	1.518 (4)	C12—H12C	0.9600
C1—H1B	0.9600	C14—C15	1.367 (4)
C1—H1C	0.9600	C14—H14A	0.9300
C1—H1D	0.9600	C15—C16	1.397 (3)
N2—C13	1.317 (3)	C15—H15A	0.9300
N2—C16	1.344 (3)	C16—C17	1.482 (4)
C2—C4	1.512 (4)	C17—C18	1.380 (4)
C2—H2B	0.9600	C17—C21	1.391 (3)
C2—H2C	0.9600	C18—C19	1.368 (4)
C2—H2D	0.9600	C18—H18A	0.9300
C3—C4	1.507 (5)	C19—C20	1.379 (4)
C3—H3B	0.9600	C19—H19A	0.9300
C3—H3C	0.9600	C20—H20A	0.9300
C3—H3D	0.9600	C21—H21A	0.9300

C5—O1—C4	122.7 (2)	C9—C8—H8A	118.9
C13—O3—C10	123.90 (19)	C10—C9—C8	116.0 (3)
C5—N1—C6	128.6 (2)	C10—C9—C12	121.7 (3)
C5—N1—H1A	115.7	C8—C9—C12	122.3 (3)
C6—N1—H1A	115.7	C9—C10—C11	124.2 (2)
C13—N2—C16	116.2 (2)	C9—C10—O3	114.6 (2)
C14—N3—C13	113.6 (2)	C11—C10—O3	120.9 (2)
C4—C1—H1B	109.5	C10—C11—C6	118.4 (2)
C4—C1—H1C	109.5	C10—C11—H11A	120.8
H1B—C1—H1C	109.5	C6—C11—H11A	120.8
C4—C1—H1D	109.5	C9—C12—H12A	109.5
H1B—C1—H1D	109.5	C9—C12—H12B	109.5
H1C—C1—H1D	109.5	H12A—C12—H12B	109.5
C4—C2—H2B	109.5	C9—C12—H12C	109.5
C4—C2—H2C	109.5	H12A—C12—H12C	109.5
H2B—C2—H2C	109.5	H12B—C12—H12C	109.5
C4—C2—H2D	109.5	N2—C13—O3	120.7 (2)
H2B—C2—H2D	109.5	N2—C13—N3	128.4 (3)
H2C—C2—H2D	109.5	O3—C13—N3	110.9 (2)
C4—C3—H3B	109.5	N3—C14—C15	124.3 (3)
C4—C3—H3C	109.5	N3—C14—H14A	117.8
H3B—C3—H3C	109.5	C15—C14—H14A	117.8
C4—C3—H3D	109.5	C14—C15—C16	117.1 (3)
H3B—C3—H3D	109.5	C14—C15—H15A	121.4
H3C—C3—H3D	109.5	C16—C15—H15A	121.4
C20—N4—C21	117.2 (2)	N2—C16—C15	120.4 (2)
O1—C4—C3	109.0 (3)	N2—C16—C17	116.8 (2)
O1—C4—C2	110.8 (2)	C15—C16—C17	122.8 (2)
C3—C4—C2	112.3 (3)	C18—C17—C21	117.2 (2)
O1—C4—C1	102.0 (2)	C18—C17—C16	122.0 (2)
C3—C4—C1	111.1 (3)	C21—C17—C16	120.8 (2)
C2—C4—C1	111.1 (3)	C19—C18—C17	119.3 (2)
O2—C5—O1	125.6 (3)	C19—C18—H18A	120.3
O2—C5—N1	126.3 (3)	C17—C18—H18A	120.3
O1—C5—N1	108.1 (2)	C18—C19—C20	119.4 (3)
C7—C6—C11	118.9 (2)	C18—C19—H19A	120.3
C7—C6—N1	117.0 (2)	C20—C19—H19A	120.3
C11—C6—N1	124.0 (2)	N4—C20—C19	122.8 (3)
C8—C7—C6	120.3 (3)	N4—C20—H20A	118.6
C8—C7—H7A	119.8	C19—C20—H20A	118.6
C6—C7—H7A	119.8	N4—C21—C17	124.0 (2)
C7—C8—C9	122.2 (3)	N4—C21—H21A	118.0
C7—C8—H8A	118.9	C17—C21—H21A	118.0

C5—O1—C4—C3	64.0 (3)	C16—N2—C13—O3	178.7 (2)
C5—O1—C4—C2	−60.1 (4)	C16—N2—C13—N3	−1.6 (4)
C5—O1—C4—C1	−178.5 (3)	C10—O3—C13—N2	−9.7 (4)
C4—O1—C5—O2	8.5 (5)	C10—O3—C13—N3	170.6 (2)
C4—O1—C5—N1	−172.4 (2)	C14—N3—C13—N2	0.8 (4)
C6—N1—C5—O2	2.1 (5)	C14—N3—C13—O3	−179.5 (2)
C6—N1—C5—O1	−177.0 (2)	C13—N3—C14—C15	1.1 (5)
C5—N1—C6—C7	−177.0 (3)	N3—C14—C15—C16	−2.0 (5)
C5—N1—C6—C11	2.9 (4)	C13—N2—C16—C15	0.5 (4)
C11—C6—C7—C8	−0.6 (4)	C13—N2—C16—C17	−178.7 (2)
N1—C6—C7—C8	179.3 (3)	C14—C15—C16—N2	1.1 (4)
C6—C7—C8—C9	0.0 (5)	C14—C15—C16—C17	−179.7 (3)
C7—C8—C9—C10	0.6 (4)	N2—C16—C17—C18	−179.7 (2)
C7—C8—C9—C12	−179.9 (3)	C15—C16—C17—C18	1.1 (4)
C8—C9—C10—C11	−0.7 (4)	N2—C16—C17—C21	0.9 (4)
C12—C9—C10—C11	179.9 (3)	C15—C16—C17—C21	−178.3 (3)
C8—C9—C10—O3	172.1 (2)	C21—C17—C18—C19	−0.6 (4)
C12—C9—C10—O3	−7.3 (4)	C16—C17—C18—C19	180.0 (2)
C13—O3—C10—C9	138.8 (3)	C17—C18—C19—C20	−0.3 (4)
C13—O3—C10—C11	−48.2 (4)	C21—N4—C20—C19	−0.4 (4)
C9—C10—C11—C6	0.1 (4)	C18—C19—C20—N4	0.8 (5)
O3—C10—C11—C6	−172.3 (2)	C20—N4—C21—C17	−0.6 (4)
C7—C6—C11—C10	0.6 (4)	C18—C17—C21—N4	1.1 (4)
N1—C6—C11—C10	−179.3 (2)	C16—C17—C21—N4	−179.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N4ⁱ	0.86	2.10	2.944 (4)	165
C15—H15A···O2ⁱⁱ	0.93	2.45	3.382 (4)	177
C18—H18A···O2ⁱⁱ	0.93	2.39	3.319 (4)	174
C3—H3B···Cg1ⁱ	0.96	2.86	3.560 (3)	131
C12—H12B···Cg2ⁱⁱⁱ	0.96	2.90	3.788 (3)	154

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₂N₄O₃
M_r	378.43
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	9.951 (2), 10.733 (2), 11.577 (2)
α, β, γ (°)	114.74 (3), 107.14 (3), 99.97 (3)
V (Å³)	1008.6 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.975, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	3882, 3652, 2333
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.184, 1.01
No. of reflections	3652
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.27

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N4ⁱ	0.86	2.10	2.944 (4)	165
C15—H15A···O2ⁱⁱ	0.93	2.45	3.382 (4)	177
C18—H18A···O2ⁱⁱ	0.93	2.39	3.319 (4)	174
C3—H3B···Cg1ⁱ	0.96	2.86	3.560 (3)	131
C12—H12B···Cg2ⁱⁱⁱ	0.96	2.90	3.788 (3)	154

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

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

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