Dipropyl 4,8-dioxo-1H,5H-2,6-dioxa-3a,4a,7a,8a-tetra-azacyclo-penta-[def]fluorene-8b,8c-dicarboxyl-ate.

The title compound, C(16)H(22)N(4)O(8), is a glycoluril derivative with two propoxycarbonyl substituents on the convex face of the glycoluril system. The dihedral angle between the five-membered rings in the glycoluril unit is 72.70 (2)°. The oxadiazinane six-membered ring displays a normal chair conformation. One of the propyl groups is disordered over two positions with site occupancies of 0.557 (7) and 0.443 (7). Inter-molecular C-H⋯O hydrogen bonds are effective in the stabilization of the crystal structure.

Related literature

For related structures, see: Branda et al. (1995 ▶); Elemans et al. (1999 ▶); Gao & Sun (2007 ▶); Isaacs & Witt (2002 ▶); Isaacs et al. (1999 ▶); Li et al. (2007 ▶); Rebek (1999 ▶); Rowan et al. (1999 ▶); She & Xi (2007 ▶); Witt et al. (2000 ▶); Wu et al. (2002 ▶).

Experimental

Crystal data

C16H22N4O8

M = 398.38

Orthorhombic,

a = 8.6399 (4) Å

b = 13.401 (7) Å

c = 16.0445 (8) Å

V = 1857.7 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 294 (2) K

0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: none

17272 measured reflections

2315 independent reflections

1967 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.123

S = 1.07

2315 reflections

263 parameters

4 restraints

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; 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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807065853/is2262sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065853/is2262Isup2.hkl

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

C16H22N4O8	F000 = 840
Mr = 398.38	Dx = 1.424 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3466 reflections
a = 8.6399 (4) Å	θ = 2.5–21.5º
b = 13.401 (7) Å	µ = 0.12 mm−1
c = 16.0445 (8) Å	T = 294 (2) K
V = 1857.7 (10) Å3	Block, colorless
Z = 4	0.20 × 0.10 × 0.10 mm

Bruker SMART APEX CCD area-detector diffractometer	1967 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.041
Monochromator: graphite	θmax = 27.0º
T = 294(2) K	θmin = 2.5º
φ and ω scans	h = −11→9
Absorption correction: none	k = −16→17
17272 measured reflections	l = −19→20
2315 independent reflections

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)] = 0.050	H-atom parameters constrained
wR(F2) = 0.123	w = 1/[σ2(Fo2) + (0.0681P)2 + 0.2494P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.002
2315 reflections	Δρmax = 0.26 e Å−3
263 parameters	Δρmin = −0.18 e Å−3
4 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	Occ. (<1)
C1	0.4167 (4)	0.2297 (2)	0.2432 (2)	0.0501 (8)
H1A	0.3680	0.2906	0.2239	0.060*
H1B	0.3651	0.1739	0.2165	0.060*
C2	0.4676 (4)	0.1327 (2)	0.3595 (2)	0.0539 (9)
H2A	0.4169	0.0760	0.3338	0.065*
H2B	0.4532	0.1278	0.4193	0.065*
C3	0.6597 (3)	0.31946 (18)	0.22249 (17)	0.0357 (6)
C4	0.7391 (4)	0.1724 (2)	0.3941 (2)	0.0484 (8)
C5	0.9211 (4)	0.3717 (2)	0.2653 (3)	0.0605 (10)
H5A	1.0236	0.3599	0.2427	0.073*
H5B	0.8884	0.4380	0.2487	0.073*
C6	0.9781 (5)	0.2689 (3)	0.3785 (3)	0.0685 (11)
H6A	0.9851	0.2662	0.4388	0.082*
H6B	1.0804	0.2564	0.3559	0.082*
C7	0.6721 (3)	0.14966 (18)	0.25409 (16)	0.0325 (6)
C8	0.6681 (3)	0.05026 (18)	0.20526 (17)	0.0356 (6)
C9	0.5560 (5)	−0.0444 (2)	0.0969 (2)	0.0569 (9)
H9A	0.5447	−0.1000	0.1352	0.068*
H9B	0.6490	−0.0549	0.0642	0.068*
C10	0.4189 (6)	−0.0385 (3)	0.0411 (3)	0.0821 (13)
H10A	0.3995	−0.1045	0.0187	0.098*
H10B	0.3299	−0.0202	0.0746	0.098*
C11	0.4299 (8)	0.0317 (5)	−0.0287 (4)	0.116 (2)
H11A	0.4263	0.0988	−0.0080	0.174*
H11B	0.3448	0.0209	−0.0662	0.174*
H11C	0.5256	0.0212	−0.0578	0.174*
C12	0.8373 (3)	0.19597 (19)	0.26092 (18)	0.0350 (6)
C13	0.9645 (4)	0.1474 (2)	0.2084 (2)	0.0426 (7)
C14	1.0282 (6)	0.1060 (3)	0.0683 (3)	0.0803 (14)
H14A	1.0758	0.0455	0.0893	0.096*	0.557 (7)
H14B	1.1091	0.1541	0.0566	0.096*	0.557 (7)
H14C	1.0186	0.0339	0.0664	0.096*	0.443 (7)
H14D	1.1337	0.1222	0.0838	0.096*	0.443 (7)
C15	0.9389 (12)	0.0845 (6)	−0.0080 (5)	0.094 (3)	0.557 (7)
H15A	0.8691	0.0294	0.0033	0.113*	0.557 (7)
H15B	1.0101	0.0630	−0.0511	0.113*	0.557 (7)
C16	0.844 (2)	0.1729 (11)	−0.0413 (12)	0.130 (5)	0.557 (7)
H16A	0.7547	0.1828	−0.0065	0.194*	0.557 (7)
H16B	0.8109	0.1589	−0.0973	0.194*	0.557 (7)
H16C	0.9064	0.2320	−0.0410	0.194*	0.557 (7)
C15'	0.9949 (14)	0.1470 (8)	−0.0134 (5)	0.094 (3)	0.443 (7)
H15C	1.0705	0.1237	−0.0537	0.113*	0.443 (7)
H15D	0.9984	0.2193	−0.0117	0.113*	0.443 (7)
C16'	0.833 (2)	0.1113 (16)	−0.0377 (16)	0.130 (5)	0.443 (7)
H16D	0.8219	0.0418	−0.0245	0.194*	0.443 (7)
H16E	0.8173	0.1209	−0.0964	0.194*	0.443 (7)
H16F	0.7566	0.1490	−0.0074	0.194*	0.443 (7)
N1	0.5792 (3)	0.23013 (15)	0.21957 (15)	0.0347 (5)
N2	0.6315 (3)	0.13036 (17)	0.34032 (15)	0.0426 (6)
N3	0.8136 (3)	0.29806 (16)	0.23239 (16)	0.0390 (6)
N4	0.8717 (3)	0.1929 (2)	0.34926 (16)	0.0471 (6)
O1	0.3994 (3)	0.22198 (15)	0.33015 (16)	0.0533 (6)
O2	0.9261 (3)	0.36549 (18)	0.35326 (18)	0.0682 (7)
O3	0.6044 (3)	0.40152 (14)	0.21303 (15)	0.0511 (6)
O4	0.7212 (4)	0.1841 (2)	0.46809 (15)	0.0726 (8)
O5	0.7493 (3)	−0.01743 (15)	0.22604 (17)	0.0561 (6)
O6	0.5676 (3)	0.05015 (13)	0.14370 (13)	0.0442 (5)
O7	1.0852 (3)	0.11865 (18)	0.23472 (19)	0.0643 (7)
O8	0.9201 (3)	0.14622 (19)	0.12965 (14)	0.0631 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0357 (17)	0.0445 (16)	0.070 (2)	0.0030 (13)	−0.0040 (16)	−0.0090 (14)
C2	0.058 (2)	0.0406 (15)	0.063 (2)	−0.0100 (15)	0.0269 (18)	−0.0051 (14)
C3	0.0426 (17)	0.0291 (12)	0.0355 (14)	0.0015 (11)	0.0017 (13)	0.0004 (10)
C4	0.066 (2)	0.0432 (16)	0.0356 (17)	0.0154 (15)	−0.0011 (16)	0.0018 (12)
C5	0.046 (2)	0.0427 (16)	0.093 (3)	−0.0112 (14)	0.003 (2)	−0.0124 (17)
C6	0.054 (2)	0.075 (2)	0.076 (3)	0.0048 (19)	−0.026 (2)	−0.023 (2)
C7	0.0319 (15)	0.0294 (12)	0.0362 (14)	0.0018 (10)	0.0036 (12)	−0.0029 (10)
C8	0.0348 (15)	0.0306 (12)	0.0413 (16)	0.0015 (11)	0.0051 (13)	−0.0027 (11)
C9	0.076 (3)	0.0388 (15)	0.056 (2)	−0.0057 (17)	0.0001 (19)	−0.0154 (14)
C10	0.076 (3)	0.081 (3)	0.089 (3)	−0.009 (2)	−0.007 (3)	−0.036 (2)
C11	0.133 (5)	0.117 (4)	0.099 (4)	0.021 (4)	−0.035 (4)	−0.004 (3)
C12	0.0306 (15)	0.0321 (12)	0.0421 (15)	0.0002 (11)	−0.0016 (12)	−0.0021 (11)
C13	0.0306 (16)	0.0367 (13)	0.060 (2)	0.0026 (12)	0.0053 (14)	−0.0013 (13)
C14	0.085 (3)	0.081 (3)	0.075 (3)	0.026 (2)	0.043 (3)	−0.002 (2)
C15	0.126 (7)	0.078 (5)	0.079 (5)	−0.022 (4)	0.064 (5)	−0.015 (4)
C16	0.151 (8)	0.170 (15)	0.068 (4)	0.011 (13)	0.023 (5)	−0.002 (12)
C15'	0.126 (7)	0.078 (5)	0.079 (5)	−0.022 (4)	0.064 (5)	−0.015 (4)
C16'	0.151 (8)	0.170 (15)	0.068 (4)	0.011 (13)	0.023 (5)	−0.002 (12)
N1	0.0300 (12)	0.0312 (10)	0.0429 (13)	0.0033 (9)	−0.0012 (11)	−0.0021 (9)
N2	0.0523 (16)	0.0358 (11)	0.0397 (13)	−0.0004 (11)	0.0086 (12)	0.0027 (10)
N3	0.0336 (13)	0.0293 (10)	0.0542 (14)	−0.0028 (9)	0.0012 (11)	−0.0011 (10)
N4	0.0431 (15)	0.0521 (14)	0.0461 (15)	0.0096 (12)	−0.0126 (13)	−0.0050 (12)
O1	0.0414 (13)	0.0464 (11)	0.0721 (16)	−0.0010 (10)	0.0205 (11)	−0.0158 (10)
O2	0.0538 (16)	0.0610 (14)	0.0899 (19)	−0.0064 (12)	−0.0132 (15)	−0.0325 (13)
O3	0.0548 (15)	0.0308 (9)	0.0676 (14)	0.0080 (9)	−0.0019 (12)	0.0057 (9)
O4	0.098 (2)	0.0832 (17)	0.0361 (13)	0.0226 (17)	−0.0014 (14)	0.0007 (12)
O5	0.0535 (13)	0.0359 (10)	0.0788 (16)	0.0124 (10)	−0.0078 (13)	−0.0107 (10)
O6	0.0537 (13)	0.0353 (9)	0.0435 (11)	−0.0003 (9)	−0.0031 (11)	−0.0082 (8)
O7	0.0360 (14)	0.0604 (14)	0.0966 (19)	0.0096 (11)	−0.0057 (14)	−0.0154 (13)
O8	0.0587 (16)	0.0793 (16)	0.0515 (14)	0.0268 (13)	0.0173 (13)	−0.0024 (12)

C1—O1	1.407 (4)	C9—H9B	0.9700
C1—N1	1.454 (4)	C10—C11	1.467 (7)
C1—H1A	0.9700	C10—H10A	0.9700
C1—H1B	0.9700	C10—H10B	0.9700
C2—O1	1.414 (4)	C11—H11A	0.9600
C2—N2	1.449 (4)	C11—H11B	0.9600
C2—H2A	0.9700	C11—H11C	0.9600
C2—H2B	0.9700	C12—N4	1.449 (4)
C3—O3	1.209 (3)	C12—N3	1.457 (3)
C3—N3	1.369 (4)	C12—C13	1.530 (4)
C3—N1	1.385 (3)	C13—O7	1.189 (4)
C4—O4	1.207 (4)	C13—O8	1.321 (4)
C4—N4	1.381 (5)	C14—C15'	1.450 (8)
C4—N2	1.388 (4)	C14—O8	1.460 (4)
C5—O2	1.414 (5)	C14—C15	1.475 (8)
C5—N3	1.455 (4)	C14—H14A	0.9700
C5—H5A	0.9700	C14—H14B	0.9700
C5—H5B	0.9700	C14—H14C	0.9700
C6—O2	1.429 (5)	C14—H14D	0.9700
C6—N4	1.450 (4)	C15—C16	1.538 (9)
C6—H6A	0.9700	C15—H15A	0.9700
C6—H6B	0.9700	C15—H15B	0.9700
C7—N2	1.451 (4)	C16—H16A	0.9600
C7—N1	1.454 (3)	C16—H16B	0.9600
C7—C8	1.546 (3)	C16—H16C	0.9600
C7—C12	1.561 (4)	C15'—C16'	1.532 (10)
C8—O5	1.194 (3)	C15'—H15C	0.9700
C8—O6	1.315 (3)	C15'—H15D	0.9700
C9—O6	1.477 (3)	C16'—H16D	0.9600
C9—C10	1.486 (6)	C16'—H16E	0.9600
C9—H9A	0.9700	C16'—H16F	0.9600
O1—C1—N1	111.2 (3)	N3—C12—C13	109.1 (2)
O1—C1—H1A	109.4	N4—C12—C7	104.2 (2)
N1—C1—H1A	109.4	N3—C12—C7	102.9 (2)
O1—C1—H1B	109.4	C13—C12—C7	116.7 (2)
N1—C1—H1B	109.4	O7—C13—O8	126.1 (3)
H1A—C1—H1B	108.0	O7—C13—C12	124.9 (3)
O1—C2—N2	110.8 (3)	O8—C13—C12	108.9 (3)
O1—C2—H2A	109.5	C15'—C14—O8	110.1 (5)
N2—C2—H2A	109.5	O8—C14—C15	107.3 (5)
O1—C2—H2B	109.5	C15'—C14—H14A	135.6
N2—C2—H2B	109.5	O8—C14—H14A	110.3
H2A—C2—H2B	108.1	C15—C14—H14A	110.3
O3—C3—N3	126.1 (3)	C15'—C14—H14B	73.5
O3—C3—N1	125.7 (3)	O8—C14—H14B	110.3
N3—C3—N1	108.1 (2)	C15—C14—H14B	110.3
O4—C4—N4	126.4 (4)	H14A—C14—H14B	108.5
O4—C4—N2	125.3 (4)	C15'—C14—H14C	109.4
N4—C4—N2	108.2 (3)	O8—C14—H14C	109.5
O2—C5—N3	110.0 (3)	C15'—C14—H14D	109.4
O2—C5—H5A	109.7	O8—C14—H14D	110.2
N3—C5—H5A	109.7	H14C—C14—H14D	108.1
O2—C5—H5B	109.7	C14—C15—C16	114.7 (9)
N3—C5—H5B	109.7	C16—C15—H14C	148.2
H5A—C5—H5B	108.2	C14—C15—H15A	108.6
O2—C6—N4	110.2 (3)	C16—C15—H15A	108.6
O2—C6—H6A	109.6	H14C—C15—H15A	78.3
N4—C6—H6A	109.6	C14—C15—H15B	108.6
O2—C6—H6B	109.6	C16—C15—H15B	108.6
N4—C6—H6B	109.6	H14C—C15—H15B	98.0
H6A—C6—H6B	108.1	H15A—C15—H15B	107.6
N2—C7—N1	111.2 (2)	C14—C15'—C16'	107.1 (12)
N2—C7—C8	108.9 (2)	C14—C15'—H15C	110.3
N1—C7—C8	115.7 (2)	C16'—C15'—H15C	110.3
N2—C7—C12	103.0 (2)	C14—C15'—H15D	110.3
N1—C7—C12	103.7 (2)	C16'—C15'—H15D	110.3
C8—C7—C12	113.5 (2)	H15C—C15'—H15D	108.6
O5—C8—O6	126.6 (2)	C15'—C16'—H16D	109.5
O5—C8—C7	120.0 (3)	C15'—C16'—H16E	109.5
O6—C8—C7	113.3 (2)	H16D—C16'—H16E	109.5
O6—C9—C10	108.3 (3)	C15'—C16'—H16F	109.5
O6—C9—H9A	110.0	H16D—C16'—H16F	109.5
C10—C9—H9A	110.0	H16E—C16'—H16F	109.5
O6—C9—H9B	110.0	C3—N1—C1	118.7 (2)
C10—C9—H9B	110.0	C3—N1—C7	110.5 (2)
H9A—C9—H9B	108.4	C1—N1—C7	115.5 (2)
C11—C10—C9	116.3 (4)	C4—N2—C2	120.9 (3)
C11—C10—H10A	108.2	C4—N2—C7	111.0 (2)
C9—C10—H10A	108.2	C2—N2—C7	115.8 (3)
C11—C10—H10B	108.2	C3—N3—C5	121.3 (2)
C9—C10—H10B	108.2	C3—N3—C12	111.7 (2)
H10A—C10—H10B	107.4	C5—N3—C12	115.7 (2)
C10—C11—H11A	109.5	C4—N4—C12	110.2 (3)
C10—C11—H11B	109.5	C4—N4—C6	119.8 (3)
H11A—C11—H11B	109.5	C12—N4—C6	115.3 (3)
C10—C11—H11C	109.5	C1—O1—C2	110.4 (2)
H11A—C11—H11C	109.5	C5—O2—C6	110.2 (3)
H11B—C11—H11C	109.5	C8—O6—C9	115.3 (2)
N4—C12—N3	111.3 (2)	C13—O8—C14	117.6 (3)
N4—C12—C13	112.3 (2)
N2—C7—C8—O5	−59.0 (4)	O1—C2—N2—C7	−51.7 (3)
N1—C7—C8—O5	174.8 (3)	N1—C7—N2—C4	−101.6 (3)
C12—C7—C8—O5	55.1 (4)	C8—C7—N2—C4	129.7 (2)
N2—C7—C8—O6	119.5 (3)	C12—C7—N2—C4	8.9 (3)
N1—C7—C8—O6	−6.6 (3)	N1—C7—N2—C2	41.1 (3)
C12—C7—C8—O6	−126.4 (3)	C8—C7—N2—C2	−87.6 (3)
O6—C9—C10—C11	69.0 (5)	C12—C7—N2—C2	151.7 (2)
N2—C7—C12—N4	2.4 (2)	O3—C3—N3—C5	25.0 (5)
N1—C7—C12—N4	118.5 (2)	N1—C3—N3—C5	−158.9 (3)
C8—C7—C12—N4	−115.2 (2)	O3—C3—N3—C12	167.0 (3)
N2—C7—C12—N3	−113.8 (2)	N1—C3—N3—C12	−17.0 (3)
N1—C7—C12—N3	2.3 (3)	O2—C5—N3—C3	88.6 (3)
C8—C7—C12—N3	128.6 (2)	O2—C5—N3—C12	−52.0 (4)
N2—C7—C12—C13	126.8 (2)	N4—C12—N3—C3	−102.3 (3)
N1—C7—C12—C13	−117.1 (2)	C13—C12—N3—C3	133.3 (3)
C8—C7—C12—C13	9.2 (3)	C7—C12—N3—C3	8.7 (3)
N4—C12—C13—O7	−6.8 (4)	N4—C12—N3—C5	42.0 (4)
N3—C12—C13—O7	117.0 (3)	C13—C12—N3—C5	−82.4 (3)
C7—C12—C13—O7	−127.0 (3)	C7—C12—N3—C5	153.0 (3)
N4—C12—C13—O8	175.3 (2)	O4—C4—N4—C12	−164.3 (3)
N3—C12—C13—O8	−60.8 (3)	N2—C4—N4—C12	19.2 (3)
C7—C12—C13—O8	55.1 (3)	O4—C4—N4—C6	−27.0 (5)
C15'—C14—C15—C16	−47.2 (12)	N2—C4—N4—C6	156.5 (3)
O8—C14—C15—C16	53.5 (10)	N3—C12—N4—C4	97.1 (3)
O8—C14—C15'—C16'	−63.6 (12)	C13—C12—N4—C4	−140.3 (2)
C15—C14—C15'—C16'	29.3 (12)	C7—C12—N4—C4	−13.1 (3)
O3—C3—N1—C1	−28.7 (4)	N3—C12—N4—C6	−42.3 (4)
N3—C3—N1—C1	155.2 (3)	C13—C12—N4—C6	80.3 (3)
O3—C3—N1—C7	−165.5 (3)	C7—C12—N4—C6	−152.5 (3)
N3—C3—N1—C7	18.4 (3)	O2—C6—N4—C4	−82.6 (4)
O1—C1—N1—C3	−83.7 (3)	O2—C6—N4—C12	52.7 (4)
O1—C1—N1—C7	51.1 (3)	N1—C1—O1—C2	−60.0 (3)
N2—C7—N1—C3	97.6 (3)	N2—C2—O1—C1	60.1 (4)
C8—C7—N1—C3	−137.4 (2)	N3—C5—O2—C6	60.9 (4)
C12—C7—N1—C3	−12.4 (3)	N4—C6—O2—C5	−61.5 (4)
N2—C7—N1—C1	−40.6 (3)	O5—C8—O6—C9	0.3 (4)
C8—C7—N1—C1	84.4 (3)	C7—C8—O6—C9	−178.1 (3)
C12—C7—N1—C1	−150.7 (2)	C10—C9—O6—C8	169.5 (3)
O4—C4—N2—C2	25.2 (5)	O7—C13—O8—C14	0.0 (5)
N4—C4—N2—C2	−158.2 (3)	C12—C13—O8—C14	177.8 (3)
O4—C4—N2—C7	165.8 (3)	C15'—C14—O8—C13	−155.8 (6)
N4—C4—N2—C7	−17.6 (3)	C15—C14—O8—C13	163.3 (4)
O1—C2—N2—C4	87.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O2i	0.97	2.58	3.482 (5)	155
C9—H9B···O4ii	0.97	2.58	3.388 (4)	141
C5—H5B···O7iii	0.97	2.45	3.310 (4)	148
C9—H9A···O1iv	0.97	2.50	3.364 (4)	149
C2—H2A···O3iv	0.97	2.46	3.368 (4)	155
C1—H1B···O7v	0.97	2.55	3.231 (4)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯O2i	0.97	2.58	3.482 (5)	155
C9—H9B⋯O4ii	0.97	2.58	3.388 (4)	141
C5—H5B⋯O7iii	0.97	2.45	3.310 (4)	148
C9—H9A⋯O1iv	0.97	2.50	3.364 (4)	149
C2—H2A⋯O3iv	0.97	2.46	3.368 (4)	155
C1—H1B⋯O7v	0.97	2.55	3.231 (4)	128

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .