1,2,13,14,14a,15,16,17,18,18a-Decahydro-1,14-methano-4H,6H,8H-1,3,5-oxadiazino[3′,4′:3,3a]benzimidazo[1,7a-b][2,4]benzodiazepine-6,19-dione

She, N.; Xi, H.

doi:10.1107/S1600536807052038

1,2,13,14,14a,15,16,17,18,18a-Decahydro-1,14-methano-4H,6H,8H-1,3,5-oxadiazino[3′,4′:3,3a]benzimidazo[1,7a-b][2,4]benzodiazepine-6,19-dione

In the title compound, C₁₈H₂₀N₄O₃, a glycoluril derivative, the oxadiazinane six-membered ring displays a chair conformation and the bridgehead cyclohexane ring a boat conformation. In the crystal structure, intermolecular C—H

O hydrogen bonds may help to establish the packing.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807052038/hb2603sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807052038/hb2603Isup2.hkl Contains datablock I

CCDC reference: 667444

checkCIF report

Key indicators

Single-crystal X-ray study
T = 297 K
Mean (C-C) = 0.002 Å
R factor = 0.045
wR factor = 0.129
Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     -   C4      ..       6.04 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   0 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

Glycolurils, due to their special pre-formed skeletal structures, are widely used as platforms or building blocks to construct a series of compounds with more sophisticated structures (e. g. Reek et al., 2003). In recent years a series of receptors derived from glycoluril have been developed (Jansen et al., 2001).

We report here the structure of the title glycoluril derivative, (I) (Fig. 1), which is an important intermediate for the preparation of glycoluril receptors (Wu et al., 2002). The bond lengths and angles present in (I) show no unusual features and are similar to those found in other similar compounds (Fettinger et al., 2004; Cao et al., 2006).

The imidazole ring A (N1/N3/C9/C11/C16) and ring B (N2/N4/C10–11/C16) are close to flat, the maximum deviation from the mean plane being 0.085 (2) Å and 0.093 (2) Å for atom C9 or N2. The dihedral angle between them is 72.28 (7)°. The C₃N₂O oxadiazinane six-membered ring displays a chair conformation.

In the crystal, weak intermolecular C—H···O hydrogen bonds lead to the formation of a tape-like structure (Fig. 2).

Related literature top

For related structures, see: Fettinger et al. (2004); Cao et al. (2006). For background, see: Jansen et al. (2001); Wu et al. (2002); Reek et al. (2003).

Experimental top

The title compound was synthesized according to the procedure of Wu et al. (2002). Colourless blocks of (I) were obtained by slow evaporation of a dichloromethane solution at 283 K.

Structure description top

In the crystal, weak intermolecular C—H···O hydrogen bonds lead to the formation of a tape-like structure (Fig. 2).

For related structures, see: Fettinger et al. (2004); Cao et al. (2006). For background, see: Jansen et al. (2001); Wu et al. (2002); Reek et al. (2003).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Figures top

	Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level for the non-hydrogen atoms.
	Fig. 2. A packing diagram for (I). C—H···O hydrogen bonds are shown as dashed lines.

1,2,13,14,14a,15,16,17,18,18a-Decahydro-1,14-methano-4H,6H,8H- 1,3,5-oxadiazino[3',4':3,3a]benzimidazo[1,7a-b][2,4]benzodiazepine- 6,19-dione top

Crystal data top

C₁₈H₂₀N₄O₃	F(000) = 720
M_r = 340.38	D_x = 1.405 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4769 reflections
a = 11.8315 (12) Å	θ = 2.4–28.2°
b = 11.3603 (11) Å	µ = 0.10 mm⁻¹
c = 11.9716 (12) Å	T = 297 K
β = 90.261 (2)°	Block, colorless
V = 1609.1 (3) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART 4K CCD diffractometer	2964 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.020
Graphite monochromator	θ_max = 27.0°, θ_min = 2.4°
ω scans	h = −13→15
9429 measured reflections	k = −10→14
3494 independent reflections	l = −14→15

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0769P)² + 0.2493P] where P = (F_o² + 2F_c²)/3
3494 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₈H₂₀N₄O₃	V = 1609.1 (3) Å³
M_r = 340.38	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.8315 (12) Å	µ = 0.10 mm⁻¹
b = 11.3603 (11) Å	T = 297 K
c = 11.9716 (12) Å	0.30 × 0.20 × 0.20 mm
β = 90.261 (2)°

Data collection top

Bruker SMART 4K CCD diffractometer	2964 reflections with I > 2σ(I)
9429 measured reflections	R_int = 0.020
3494 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.05	Δρ_max = 0.22 e Å⁻³
3494 reflections	Δρ_min = −0.24 e Å⁻³
226 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
N2	1.00013 (9)	0.16297 (9)	0.17388 (9)	0.0371 (3)
N3	0.87562 (9)	0.04324 (10)	0.39525 (9)	0.0393 (3)
O1	0.93433 (10)	0.18108 (9)	0.52572 (8)	0.0525 (3)
C11	1.02131 (10)	0.07801 (11)	0.26298 (10)	0.0329 (3)
C9	0.94842 (11)	0.12802 (11)	0.43866 (11)	0.0384 (3)
O2	0.84406 (10)	0.26030 (10)	0.10290 (9)	0.0566 (3)
N1	1.03911 (9)	0.13619 (10)	0.36993 (9)	0.0380 (3)
O3	0.70042 (9)	0.13063 (10)	0.34834 (11)	0.0599 (3)
N4	0.82993 (9)	0.08765 (10)	0.20448 (10)	0.0409 (3)
C16	0.90377 (10)	0.01906 (11)	0.27860 (10)	0.0341 (3)
C10	0.88658 (12)	0.18055 (12)	0.15638 (11)	0.0399 (3)
C12	1.11293 (11)	−0.01106 (13)	0.23557 (12)	0.0435 (3)
H12A	1.1827	0.0304	0.2195	0.052*
H12B	1.1261	−0.0607	0.3002	0.052*
C15	0.90251 (12)	−0.11112 (11)	0.24948 (12)	0.0395 (3)
H15A	0.8251	−0.1391	0.2461	0.047*
H15B	0.9420	−0.1553	0.3069	0.047*
C6	1.08589 (11)	0.35691 (12)	0.22752 (12)	0.0419 (3)
C13	1.08184 (14)	−0.08793 (14)	0.13630 (14)	0.0526 (4)
H13A	1.1315	−0.1559	0.1353	0.063*
H13B	1.0947	−0.0438	0.0682	0.063*
C7	1.08185 (13)	0.25468 (13)	0.14646 (11)	0.0447 (3)
H7A	1.0642	0.2850	0.0727	0.054*
H7B	1.1564	0.2194	0.1431	0.054*
C8	1.13119 (12)	0.21882 (13)	0.38893 (12)	0.0460 (3)
H8A	1.1995	0.1872	0.3559	0.055*
H8B	1.1442	0.2258	0.4687	0.055*
C17	0.75673 (13)	0.04987 (15)	0.42045 (14)	0.0538 (4)
H17A	0.7231	−0.0275	0.4123	0.065*
H17B	0.7471	0.0747	0.4974	0.065*
C5	1.06832 (13)	0.47048 (14)	0.18786 (16)	0.0544 (4)
H5	1.0519	0.4822	0.1126	0.065*
C1	1.10963 (11)	0.34032 (13)	0.34123 (12)	0.0429 (3)
C18	0.71283 (12)	0.09427 (15)	0.23565 (15)	0.0544 (4)
H18A	0.6741	0.1496	0.1870	0.065*
H18B	0.6780	0.0177	0.2258	0.065*
C14	0.95944 (13)	−0.13044 (13)	0.13732 (12)	0.0468 (3)
H14A	0.9172	−0.0890	0.0799	0.056*
H14B	0.9576	−0.2137	0.1194	0.056*
C3	1.09754 (15)	0.55057 (15)	0.37046 (19)	0.0662 (5)
H3	1.1015	0.6148	0.4184	0.079*
C4	1.07500 (14)	0.56673 (15)	0.2592 (2)	0.0672 (5)
H4	1.0641	0.6423	0.2313	0.081*
C2	1.11438 (14)	0.43785 (15)	0.41086 (16)	0.0569 (4)
H2	1.1292	0.4272	0.4865	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N2	0.0430 (6)	0.0330 (5)	0.0352 (5)	−0.0025 (5)	−0.0016 (4)	0.0022 (4)
N3	0.0402 (6)	0.0360 (6)	0.0417 (6)	−0.0005 (5)	0.0086 (4)	−0.0033 (5)
O1	0.0746 (7)	0.0445 (6)	0.0384 (5)	0.0023 (5)	0.0057 (5)	−0.0076 (4)
C11	0.0354 (6)	0.0303 (6)	0.0331 (6)	−0.0004 (5)	−0.0008 (5)	0.0000 (5)
C9	0.0487 (8)	0.0312 (6)	0.0354 (6)	0.0035 (5)	0.0003 (5)	0.0010 (5)
O2	0.0676 (7)	0.0432 (6)	0.0590 (7)	0.0108 (5)	−0.0153 (5)	0.0088 (5)
N1	0.0428 (6)	0.0380 (6)	0.0332 (5)	−0.0068 (5)	−0.0018 (4)	−0.0007 (4)
O3	0.0417 (6)	0.0529 (7)	0.0850 (8)	0.0110 (5)	0.0086 (5)	−0.0094 (6)
N4	0.0357 (6)	0.0355 (6)	0.0514 (7)	0.0032 (4)	−0.0069 (5)	0.0001 (5)
C16	0.0334 (6)	0.0308 (6)	0.0380 (6)	0.0016 (5)	0.0003 (5)	−0.0007 (5)
C10	0.0479 (7)	0.0324 (7)	0.0393 (7)	0.0046 (5)	−0.0071 (5)	−0.0042 (5)
C12	0.0364 (7)	0.0408 (7)	0.0533 (8)	0.0045 (6)	0.0057 (6)	0.0031 (6)
C15	0.0419 (7)	0.0294 (6)	0.0471 (7)	−0.0013 (5)	0.0005 (5)	−0.0016 (5)
C6	0.0343 (6)	0.0362 (7)	0.0553 (8)	−0.0047 (5)	0.0063 (6)	0.0020 (6)
C13	0.0620 (9)	0.0405 (8)	0.0553 (9)	0.0048 (7)	0.0191 (7)	−0.0053 (7)
C7	0.0531 (8)	0.0430 (8)	0.0381 (7)	−0.0070 (6)	0.0059 (6)	0.0051 (6)
C8	0.0472 (8)	0.0471 (8)	0.0437 (7)	−0.0101 (6)	−0.0076 (6)	−0.0024 (6)
C17	0.0461 (8)	0.0502 (9)	0.0652 (10)	−0.0006 (7)	0.0181 (7)	−0.0042 (7)
C5	0.0410 (8)	0.0422 (8)	0.0801 (11)	−0.0021 (6)	0.0037 (7)	0.0106 (8)
C1	0.0367 (7)	0.0406 (7)	0.0514 (8)	−0.0081 (6)	0.0076 (6)	−0.0064 (6)
C18	0.0357 (7)	0.0482 (9)	0.0791 (11)	0.0037 (6)	−0.0071 (7)	−0.0054 (8)
C14	0.0612 (9)	0.0366 (7)	0.0427 (7)	0.0046 (6)	−0.0013 (6)	−0.0060 (6)
C3	0.0530 (9)	0.0454 (9)	0.1005 (15)	−0.0072 (7)	0.0239 (9)	−0.0274 (9)
C4	0.0434 (9)	0.0354 (8)	0.1228 (18)	0.0020 (6)	0.0160 (9)	0.0013 (9)
C2	0.0521 (9)	0.0534 (9)	0.0653 (10)	−0.0136 (7)	0.0150 (7)	−0.0190 (8)

Geometric parameters (Å, º) top

N2—C10	1.3734 (17)	C6—C5	1.390 (2)
N2—C11	1.4593 (16)	C6—C1	1.401 (2)
N2—C7	1.4598 (17)	C6—C7	1.514 (2)
N3—C9	1.3912 (17)	C13—C14	1.527 (2)
N3—C17	1.4419 (18)	C13—H13A	0.9700
N3—C16	1.4631 (17)	C13—H13B	0.9700
O1—C9	1.2161 (16)	C7—H7A	0.9700
C11—N1	1.4554 (16)	C7—H7B	0.9700
C11—C12	1.5198 (18)	C8—C1	1.515 (2)
C11—C16	1.5556 (17)	C8—H8A	0.9700
C9—N1	1.3582 (17)	C8—H8B	0.9700
O2—C10	1.2169 (16)	C17—H17A	0.9700
N1—C8	1.4552 (17)	C17—H17B	0.9700
O3—C18	1.419 (2)	C5—C4	1.390 (3)
O3—C17	1.423 (2)	C5—H5	0.9300
N4—C10	1.3777 (19)	C1—C2	1.387 (2)
N4—C18	1.4384 (18)	C18—H18A	0.9700
N4—C16	1.4665 (16)	C18—H18B	0.9700
C16—C15	1.5195 (18)	C14—H14A	0.9700
C12—C13	1.519 (2)	C14—H14B	0.9700
C12—H12A	0.9700	C3—C4	1.369 (3)
C12—H12B	0.9700	C3—C2	1.383 (3)
C15—C14	1.521 (2)	C3—H3	0.9300
C15—H15A	0.9700	C4—H4	0.9300
C15—H15B	0.9700	C2—H2	0.9300

C10—N2—C11	111.86 (10)	C12—C13—H13B	108.8
C10—N2—C7	120.69 (11)	C14—C13—H13B	108.8
C11—N2—C7	121.65 (11)	H13A—C13—H13B	107.7
C9—N3—C17	119.25 (11)	N2—C7—C6	114.99 (11)
C9—N3—C16	110.08 (10)	N2—C7—H7A	108.5
C17—N3—C16	115.85 (11)	C6—C7—H7A	108.5
N1—C11—N2	111.49 (10)	N2—C7—H7B	108.5
N1—C11—C12	113.07 (10)	C6—C7—H7B	108.5
N2—C11—C12	113.75 (10)	H7A—C7—H7B	107.5
N1—C11—C16	102.45 (9)	N1—C8—C1	113.84 (11)
N2—C11—C16	102.83 (9)	N1—C8—H8A	108.8
C12—C11—C16	112.23 (10)	C1—C8—H8A	108.8
O1—C9—N1	126.66 (13)	N1—C8—H8B	108.8
O1—C9—N3	125.18 (13)	C1—C8—H8B	108.8
N1—C9—N3	108.09 (11)	H8A—C8—H8B	107.7
C9—N1—C8	122.84 (11)	O3—C17—N3	111.18 (12)
C9—N1—C11	112.98 (10)	O3—C17—H17A	109.4
C8—N1—C11	122.39 (11)	N3—C17—H17A	109.4
C18—O3—C17	109.80 (11)	O3—C17—H17B	109.4
C10—N4—C18	122.64 (12)	N3—C17—H17B	109.4
C10—N4—C16	111.74 (10)	H17A—C17—H17B	108.0
C18—N4—C16	116.27 (12)	C4—C5—C6	120.82 (18)
N3—C16—N4	109.89 (10)	C4—C5—H5	119.6
N3—C16—C15	113.56 (11)	C6—C5—H5	119.6
N4—C16—C15	111.91 (11)	C2—C1—C6	118.92 (15)
N3—C16—C11	103.97 (10)	C2—C1—C8	119.66 (14)
N4—C16—C11	103.23 (10)	C6—C1—C8	121.43 (12)
C15—C16—C11	113.53 (10)	O3—C18—N4	111.45 (12)
O2—C10—N2	126.18 (14)	O3—C18—H18A	109.3
O2—C10—N4	126.12 (13)	N4—C18—H18A	109.3
N2—C10—N4	107.59 (11)	O3—C18—H18B	109.3
C13—C12—C11	112.42 (12)	N4—C18—H18B	109.3
C13—C12—H12A	109.1	H18A—C18—H18B	108.0
C11—C12—H12A	109.1	C15—C14—C13	112.66 (12)
C13—C12—H12B	109.1	C15—C14—H14A	109.1
C11—C12—H12B	109.1	C13—C14—H14A	109.1
H12A—C12—H12B	107.9	C15—C14—H14B	109.1
C16—C15—C14	109.82 (11)	C13—C14—H14B	109.1
C16—C15—H15A	109.7	H14A—C14—H14B	107.8
C14—C15—H15A	109.7	C4—C3—C2	119.43 (16)
C16—C15—H15B	109.7	C4—C3—H3	120.3
C14—C15—H15B	109.7	C2—C3—H3	120.3
H15A—C15—H15B	108.2	C3—C4—C5	120.17 (17)
C5—C6—C1	119.05 (14)	C3—C4—H4	119.9
C5—C6—C7	119.26 (14)	C5—C4—H4	119.9
C1—C6—C7	121.67 (13)	C3—C2—C1	121.59 (18)
C12—C13—C14	113.71 (12)	C3—C2—H2	119.2
C12—C13—H13A	108.8	C1—C2—H2	119.2
C14—C13—H13A	108.8

C10—N2—C11—N1	−94.60 (12)	C7—N2—C10—O2	12.3 (2)
C7—N2—C11—N1	58.67 (15)	C11—N2—C10—N4	−17.78 (14)
C10—N2—C11—C12	136.10 (12)	C7—N2—C10—N4	−171.35 (11)
C7—N2—C11—C12	−70.62 (15)	C18—N4—C10—O2	−24.9 (2)
C10—N2—C11—C16	14.50 (13)	C16—N4—C10—O2	−170.16 (13)
C7—N2—C11—C16	167.77 (11)	C18—N4—C10—N2	158.67 (12)
C17—N3—C9—O1	28.9 (2)	C16—N4—C10—N2	13.46 (15)
C16—N3—C9—O1	166.34 (13)	N1—C11—C12—C13	168.61 (11)
C17—N3—C9—N1	−154.01 (12)	N2—C11—C12—C13	−62.90 (15)
C16—N3—C9—N1	−16.56 (14)	C16—C11—C12—C13	53.32 (15)
O1—C9—N1—C8	−4.4 (2)	N3—C16—C15—C14	−166.31 (11)
N3—C9—N1—C8	178.55 (11)	N4—C16—C15—C14	68.56 (14)
O1—C9—N1—C11	−169.48 (13)	C11—C16—C15—C14	−47.82 (15)
N3—C9—N1—C11	13.47 (15)	C11—C12—C13—C14	−42.71 (18)
N2—C11—N1—C9	104.29 (12)	C10—N2—C7—C6	75.03 (16)
C12—C11—N1—C9	−126.05 (12)	C11—N2—C7—C6	−75.93 (16)
C16—C11—N1—C9	−5.05 (13)	C5—C6—C7—N2	−123.34 (14)
N2—C11—N1—C8	−60.86 (15)	C1—C6—C7—N2	58.23 (18)
C12—C11—N1—C8	68.80 (16)	C9—N1—C8—C1	−85.48 (16)
C16—C11—N1—C8	−170.20 (12)	C11—N1—C8—C1	78.21 (16)
C9—N3—C16—N4	−96.99 (12)	C18—O3—C17—N3	59.77 (16)
C17—N3—C16—N4	42.05 (15)	C9—N3—C17—O3	82.31 (16)
C9—N3—C16—C15	136.81 (11)	C16—N3—C17—O3	−52.80 (16)
C17—N3—C16—C15	−84.16 (14)	C1—C6—C5—C4	0.5 (2)
C9—N3—C16—C11	12.94 (13)	C7—C6—C5—C4	−177.93 (14)
C17—N3—C16—C11	151.98 (11)	C5—C6—C1—C2	0.3 (2)
C10—N4—C16—N3	106.11 (12)	C7—C6—C1—C2	178.71 (13)
C18—N4—C16—N3	−41.49 (15)	C5—C6—C1—C8	−179.11 (13)
C10—N4—C16—C15	−126.76 (12)	C7—C6—C1—C8	−0.7 (2)
C18—N4—C16—C15	85.64 (14)	N1—C8—C1—C2	123.37 (14)
C10—N4—C16—C11	−4.30 (14)	N1—C8—C1—C6	−57.23 (18)
C18—N4—C16—C11	−151.90 (11)	C17—O3—C18—N4	−59.14 (16)
N1—C11—C16—N3	−4.75 (12)	C10—N4—C18—O3	−92.18 (16)
N2—C11—C16—N3	−120.54 (10)	C16—N4—C18—O3	51.59 (17)
C12—C11—C16—N3	116.83 (11)	C16—C15—C14—C13	59.16 (16)
N1—C11—C16—N4	110.00 (10)	C12—C13—C14—C15	−13.33 (18)
N2—C11—C16—N4	−5.79 (12)	C2—C3—C4—C5	0.5 (3)
C12—C11—C16—N4	−128.42 (11)	C6—C5—C4—C3	−0.9 (2)
N1—C11—C16—C15	−128.64 (11)	C4—C3—C2—C1	0.4 (3)
N2—C11—C16—C15	115.58 (11)	C6—C1—C2—C3	−0.7 (2)
C12—C11—C16—C15	−7.06 (15)	C8—C1—C2—C3	178.67 (14)
C11—N2—C10—O2	165.84 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15B···O1ⁱ	0.97	2.49	3.3991 (18)	156
C17—H17A···O2ⁱⁱ	0.97	2.54	3.510 (2)	174
C12—H12B···O1ⁱ	0.97	2.60	3.4963 (18)	155
C3—H3···O1ⁱⁱⁱ	0.93	2.45	3.3144 (19)	155

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+3/2, y−1/2, −z+1/2; (iii) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₀N₄O₃
M_r	340.38
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	297
a, b, c (Å)	11.8315 (12), 11.3603 (11), 11.9716 (12)
β (°)	90.261 (2)
V (Å³)	1609.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART 4K CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9429, 3494, 2964
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.129, 1.05
No. of reflections	3494
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.24

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXTL (Bruker, 2001).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15B···O1ⁱ	0.97	2.49	3.3991 (18)	156
C17—H17A···O2ⁱⁱ	0.97	2.54	3.510 (2)	174
C12—H12B···O1ⁱ	0.97	2.60	3.4963 (18)	155
C3—H3···O1ⁱⁱⁱ	0.93	2.45	3.3144 (19)	155

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+3/2, y−1/2, −z+1/2; (iii) −x+2, −y+1, −z+1.

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