Ethyl (3-nitro-2-oxo-1,2-dihydro­pyridin-1-yl)acetate

The title compound, C₉H₁₀N₂O₅, crystallizes with two crystallographically independent mol­ecules in the asymmetric unit. In the crystal structure, the nitro­pyridone rings are connected by weak C—H...O inter­actions, forming sheet-like arrays, which are in turn linked by C—H...π and π–π inter­actions between the nitro­pyridone rings on one side, and by C—H...O and van der Waals inter­actions between the ester groups on the other.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.045
• wR factor = 0.143
• Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.84 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C8
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N13
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C18
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C9     -   C10    ...       1.41 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5     ..  O32     ..       2.64 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H172   ..  O132    ..       2.67 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C9 H10 N2 O5

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 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
   6 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
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: MSC/AFC7 Diffractometer Control Software (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC7 Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 2001); program(s) used to solve structure: TEXSAN for Windows; program(s) used to refine structure: TEXSAN for Windows and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN for Windows and PLATON (Spek, 2003).

Ethyl (3-nitro-2-oxo-1,2-dihydropyridin-1-yl)acetate

Crystal data

C9H10N2O5	F(000) = 944
Mr = 226.19	Dx = 1.428 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 23 reflections
a = 20.175 (4) Å	θ = 12.7–16.7°
b = 8.333 (3) Å	µ = 0.12 mm^−1
c = 12.729 (4) Å	T = 295 K
β = 100.49 (2)°	Prismatic, yellow
V = 2104.2 (11) Å^3	0.40 × 0.30 × 0.20 mm
Z = 8

Data collection

Rigaku AFC-7R diffractometer	Rint = 0.027
Radiation source: Rigaku rotating anode	θmax = 25.0°, θmin = 2.7°
Graphite monochromator	h = −11→23
ω/2θ scans	k = 0→9
4183 measured reflections	l = −15→14
3689 independent reflections	3 standard reflections every 150 reflections
1988 reflections with I > 2σ(I)	intensity decay: 1.1%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.143	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.058P)^2 + 0.4402P] where P = (Fo^2 + 2Fc^2)/3
3689 reflections	(Δ/σ)max = 0.010
289 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Special details

Experimental. The scan width was (1.63 + 0.30tanθ)° with an ω scan speed of 16° per minute (up to 4 scans to achieve I/σ(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

IR (ν_max, KBr, cm^-1): 3085, 1748, 1671, 1534, 1297, 1214

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 (Ų)

	x	y	z	Uiso*/Ueq
O2	0.34456 (11)	−0.1499 (2)	0.79913 (14)	0.0687 (8)
O8	0.47409 (12)	0.1158 (3)	0.89107 (19)	0.0925 (10)
O9	0.43057 (10)	0.2171 (3)	0.73198 (15)	0.0733 (8)
O31	0.33100 (14)	−0.4934 (3)	1.0256 (2)	0.0951 (10)
O32	0.30469 (13)	−0.4403 (3)	0.85870 (19)	0.0858 (10)
N1	0.34604 (10)	0.0403 (2)	0.92549 (15)	0.0437 (7)
N3	0.32261 (12)	−0.3981 (3)	0.9518 (2)	0.0574 (8)
C2	0.34050 (13)	−0.1208 (3)	0.89165 (19)	0.0436 (8)
C3	0.33221 (13)	−0.2291 (3)	0.97570 (19)	0.0433 (8)
C4	0.33290 (13)	−0.1817 (3)	1.07785 (19)	0.0512 (9)
C5	0.33973 (15)	−0.0202 (4)	1.1040 (2)	0.0599 (11)
C6	0.34569 (14)	0.0866 (3)	1.0268 (2)	0.0542 (10)
C7	0.35540 (14)	0.1577 (3)	0.8440 (2)	0.0543 (10)
C8	0.42699 (15)	0.1590 (3)	0.8272 (2)	0.0535 (10)
C9	0.49605 (19)	0.2295 (5)	0.7013 (3)	0.0966 (16)
C10	0.5037 (2)	0.1128 (6)	0.6237 (4)	0.123 (2)
O12	0.17287 (11)	−0.2220 (3)	0.53491 (16)	0.0749 (8)
O18	0.04113 (12)	−0.3485 (3)	0.6644 (2)	0.0882 (10)
O19	0.07657 (10)	−0.6004 (2)	0.64946 (17)	0.0737 (9)
O131	0.21195 (15)	0.2573 (3)	0.5656 (3)	0.1175 (13)
O132	0.16398 (16)	0.0791 (4)	0.4549 (2)	0.1203 (15)
N11	0.16965 (11)	−0.2334 (3)	0.71095 (17)	0.0526 (8)
N13	0.18579 (15)	0.1253 (4)	0.5448 (3)	0.0799 (12)
C12	0.17389 (13)	−0.1481 (3)	0.6180 (2)	0.0509 (10)
C13	0.18096 (13)	0.0221 (3)	0.6356 (2)	0.0558 (10)
C14	0.18157 (15)	0.0896 (4)	0.7326 (3)	0.0682 (13)
C15	0.17498 (16)	−0.0051 (5)	0.8198 (2)	0.0735 (14)
C16	0.16933 (15)	−0.1648 (4)	0.8062 (2)	0.0636 (11)
C17	0.15896 (15)	−0.4068 (4)	0.6997 (3)	0.0663 (11)
C18	0.08560 (16)	−0.4447 (4)	0.6695 (2)	0.0605 (11)
C19	0.00639 (16)	−0.6572 (4)	0.6270 (3)	0.0821 (14)
C20	0.00628 (18)	−0.8240 (5)	0.5896 (3)	0.0984 (16)
H4	0.32870	−0.25870	1.13120	0.0610*
H5	0.34020	0.01450	1.17530	0.0720*
H6	0.34970	0.19740	1.04430	0.0650*
H71	0.32670	0.13080	0.77860	0.0650*
H72	0.34400	0.26130	0.86620	0.0650*
H91	0.50050	0.33350	0.67270	0.1170*
H92	0.53000	0.21450	0.76280	0.1170*
H101	0.53960	0.14380	0.58910	0.1470*
H102	0.46320	0.10530	0.57300	0.1470*
H103	0.51380	0.01220	0.65790	0.1470*
H14	0.18650	0.20250	0.74110	0.0820*
H15	0.17440	0.04180	0.88770	0.0880*
H16	0.16500	−0.23070	0.86540	0.0760*
H171	0.18170	−0.44590	0.64570	0.0800*
H172	0.17660	−0.45750	0.76560	0.0800*
H191	−0.01230	−0.65210	0.69020	0.0990*
H192	−0.01940	−0.59200	0.57330	0.0990*
H201	−0.03820	−0.86540	0.58030	0.1170*
H202	0.03520	−0.88640	0.64100	0.1170*
H203	0.02170	−0.82700	0.52350	0.1170*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.1140 (17)	0.0561 (12)	0.0401 (11)	0.0035 (11)	0.0250 (11)	−0.0066 (9)
O8	0.0683 (15)	0.118 (2)	0.0891 (17)	0.0083 (14)	0.0087 (12)	0.0397 (15)
O9	0.0725 (14)	0.0860 (16)	0.0649 (13)	−0.0108 (12)	0.0217 (11)	0.0183 (12)
O31	0.137 (2)	0.0456 (13)	0.0979 (18)	0.0018 (13)	0.0083 (15)	0.0236 (13)
O32	0.121 (2)	0.0540 (14)	0.0791 (16)	−0.0108 (13)	0.0091 (14)	−0.0211 (12)
N1	0.0549 (13)	0.0354 (11)	0.0430 (12)	0.0034 (10)	0.0144 (10)	0.0011 (10)
N3	0.0630 (15)	0.0404 (13)	0.0677 (16)	0.0021 (11)	0.0094 (12)	0.0003 (13)
C2	0.0539 (16)	0.0390 (14)	0.0391 (14)	0.0054 (12)	0.0113 (11)	−0.0027 (11)
C3	0.0510 (15)	0.0352 (14)	0.0432 (14)	0.0015 (11)	0.0072 (11)	0.0022 (11)
C4	0.0580 (17)	0.0550 (17)	0.0416 (15)	−0.0016 (14)	0.0116 (12)	0.0068 (13)
C5	0.080 (2)	0.064 (2)	0.0379 (15)	−0.0080 (16)	0.0166 (14)	−0.0098 (14)
C6	0.0672 (18)	0.0437 (16)	0.0546 (17)	−0.0034 (13)	0.0185 (14)	−0.0132 (13)
C7	0.0636 (18)	0.0429 (15)	0.0584 (17)	0.0066 (13)	0.0162 (14)	0.0113 (13)
C8	0.0619 (19)	0.0412 (15)	0.0584 (18)	−0.0007 (14)	0.0136 (14)	0.0075 (13)
C9	0.083 (2)	0.118 (3)	0.101 (3)	−0.028 (2)	0.049 (2)	−0.002 (2)
C10	0.095 (3)	0.135 (4)	0.153 (4)	−0.003 (3)	0.057 (3)	−0.031 (3)
O12	0.0931 (16)	0.0795 (15)	0.0524 (12)	0.0037 (12)	0.0137 (11)	−0.0155 (12)
O18	0.0665 (15)	0.0758 (16)	0.121 (2)	0.0005 (13)	0.0133 (14)	−0.0138 (14)
O19	0.0637 (14)	0.0567 (13)	0.0987 (17)	−0.0092 (11)	0.0096 (12)	0.0022 (11)
O131	0.125 (2)	0.0655 (17)	0.176 (3)	−0.0125 (16)	0.065 (2)	0.0161 (18)
O132	0.143 (3)	0.131 (3)	0.0842 (19)	−0.012 (2)	0.0133 (18)	0.0423 (19)
N11	0.0555 (14)	0.0502 (14)	0.0501 (13)	−0.0004 (11)	0.0042 (11)	0.0012 (11)
N13	0.075 (2)	0.069 (2)	0.101 (2)	0.0037 (16)	0.0302 (18)	0.0214 (18)
C12	0.0495 (16)	0.0552 (18)	0.0477 (16)	0.0006 (13)	0.0079 (12)	−0.0025 (14)
C13	0.0485 (17)	0.0530 (18)	0.0659 (19)	0.0021 (13)	0.0107 (14)	0.0053 (15)
C14	0.0560 (19)	0.0559 (19)	0.091 (3)	0.0030 (15)	0.0092 (17)	−0.0179 (18)
C15	0.066 (2)	0.097 (3)	0.0552 (19)	0.0059 (19)	0.0049 (15)	−0.0238 (19)
C16	0.0620 (19)	0.080 (2)	0.0468 (17)	0.0010 (17)	0.0044 (13)	−0.0013 (16)
C17	0.064 (2)	0.0530 (18)	0.077 (2)	−0.0021 (15)	−0.0005 (16)	0.0103 (16)
C18	0.063 (2)	0.060 (2)	0.0582 (18)	−0.0056 (17)	0.0099 (15)	0.0050 (15)
C19	0.060 (2)	0.079 (2)	0.107 (3)	−0.0164 (18)	0.0146 (18)	0.004 (2)
C20	0.076 (2)	0.085 (3)	0.129 (3)	−0.016 (2)	0.005 (2)	−0.020 (2)

Geometric parameters (Å, º)

O2—C2	1.220 (3)	C4—H4	0.9500
O8—C8	1.188 (4)	C5—H5	0.9500
O9—C8	1.319 (3)	C6—H6	0.9500
O9—C9	1.448 (4)	C7—H72	0.9500
O31—N3	1.218 (4)	C7—H71	0.9500
O32—N3	1.226 (3)	C9—H92	0.9500
O12—C12	1.221 (3)	C9—H91	0.9500
O18—C18	1.196 (4)	C10—H101	0.9500
O19—C19	1.471 (4)	C10—H102	0.9500
O19—C18	1.328 (4)	C10—H103	0.9500
O131—N13	1.228 (4)	C12—C13	1.439 (4)
O132—N13	1.212 (5)	C13—C14	1.355 (4)
N1—C2	1.408 (3)	C14—C15	1.388 (5)
N1—C6	1.347 (3)	C15—C16	1.344 (5)
N1—C7	1.463 (3)	C17—C18	1.494 (5)
N3—C3	1.446 (4)	C19—C20	1.469 (5)
N11—C12	1.396 (3)	C14—H14	0.9500
N11—C16	1.342 (4)	C15—H15	0.9500
N11—C17	1.464 (4)	C16—H16	0.9500
N13—C13	1.458 (4)	C17—H171	0.9500
C2—C3	1.433 (3)	C17—H172	0.9500
C3—C4	1.357 (3)	C19—H191	0.9500
C4—C5	1.387 (4)	C19—H192	0.9500
C5—C6	1.347 (4)	C20—H201	0.9500
C7—C8	1.498 (4)	C20—H202	0.9500
C9—C10	1.415 (6)	C20—H203	0.9500
O2···O32	2.702 (3)	C5···O9^ix	3.362 (4)
O2···N3	2.926 (3)	C5···O131^ix	3.350 (4)
O2···C8	3.050 (3)	C6···O8	3.374 (4)
O2···C9^i	3.370 (5)	C6···O9^ix	3.287 (3)
O2···C4^ii	3.117 (3)	C6···O131^ix	3.115 (4)
O8···C6	3.374 (4)	C7···C14	3.581 (4)
O8···N1	2.770 (3)	C8···O2	3.050 (3)
O8···C2	3.340 (4)	C9···O2^x	3.370 (5)
O9···C6^iii	3.287 (3)	C12···O18	3.300 (4)
O9···C5^iii	3.362 (4)	C14···O19^viii	3.386 (4)
O12···C16^ii	3.049 (4)	C14···C7	3.581 (4)
O12···C18	3.252 (4)	C15···C2	3.436 (4)
O12···N13	2.906 (4)	C16···O12^vi	3.049 (4)
O12···C4^ii	3.275 (4)	C16···O18	3.254 (4)
O12···O132	2.702 (4)	C16···C2	3.446 (4)
O18···C16	3.254 (4)	C17···O32	3.264 (4)
O18···C19^iv	3.382 (5)	C18···O12	3.252 (4)
O18···C12	3.300 (4)	C19···O18^xi	3.382 (5)
O18···N11	2.727 (4)	C2···H101^i	3.0900
O19···C14^v	3.386 (4)	C3···H101^i	3.0400
O31···N13^vi	3.180 (4)	C8···H91^i	3.0800
O32···O2	2.702 (3)	C9···H103^x	2.9900
O32···C17	3.264 (4)	C13···H202^viii	3.0500
O2···H4^ii	2.2400	C14···H202^viii	2.9800
O2···H71	2.3700	C14···H71	2.9000
O8···H91^i	2.5700	H4···O2^vi	2.2400
O8···H92	2.3000	H4···O31	2.3800
O9···H6^iii	2.7300	H5···O9^ix	2.8900
O9···H5^iii	2.8900	H5···O32^vi	2.6400
O12···H16^ii	2.1700	H6···O31^viii	2.6100
O12···H171	2.3300	H6···O131^ix	2.8700
O18···H192	2.5400	H6···H72	2.3100
O18···H203^vii	2.8900	H6···O9^ix	2.7300
O18···H191	2.7900	H14···O131	2.4200
O18···H191^iv	2.6100	H14···O19^viii	2.8300
O19···H14^v	2.8300	H15···O131^ix	2.8100
O31···H4	2.3800	H16···H172	2.3100
O131···C6^iii	3.115 (4)	H16···O12^vi	2.1700
O131···C5^iii	3.350 (4)	H71···O2	2.3700
O31···H6^v	2.6100	H71···C14	2.9000
O31···H102^vi	2.7900	H72···O32^viii	2.6100
O32···H72^v	2.6100	H72···H6	2.3100
O32···H5^ii	2.6400	H91···O8^x	2.5700
O132···O12	2.702 (4)	H91···C8^x	3.0800
O32···H172	2.6400	H92···O8	2.3000
O131···H15^iii	2.8100	H101···N3^x	2.9400
O131···H171^viii	2.7800	H101···C2^x	3.0900
O131···H14	2.4200	H101···C3^x	3.0400
O131···H6^iii	2.8700	H102···O31^ii	2.7900
O132···H172^ii	2.6700	H103···C9^i	2.9900
N1···O8	2.770 (3)	H171···O12	2.3300
N3···O2	2.926 (3)	H171···O131^v	2.7800
N11···O18	2.727 (4)	H172···O32	2.6400
N13···O12	2.906 (4)	H172···H16	2.3100
N13···O31^ii	3.180 (4)	H172···O132^vi	2.6700
N3···H101^i	2.9400	H191···O18	2.7900
C2···C15	3.436 (4)	H191···O18^xi	2.6100
C2···O8	3.340 (4)	H192···O18	2.5400
C2···C16	3.446 (4)	H202···C13^v	3.0500
C4···O2^vi	3.117 (3)	H202···C14^v	2.9800
C4···O12^vi	3.275 (4)	H203···O18^vii	2.8900
C8—O9—C9	118.6 (2)	H91—C9—H92	109.00
C18—O19—C19	116.4 (2)	C9—C10—H101	109.00
C2—N1—C6	123.5 (2)	C9—C10—H102	109.00
C6—N1—C7	120.73 (19)	C9—C10—H103	109.00
C2—N1—C7	115.72 (19)	H101—C10—H102	110.00
O31—N3—O32	122.3 (3)	H101—C10—H103	110.00
O32—N3—C3	119.2 (2)	H102—C10—H103	110.00
O31—N3—C3	118.6 (2)	O12—C12—N11	118.9 (2)
C12—N11—C17	116.8 (2)	O12—C12—C13	128.1 (2)
C16—N11—C17	119.0 (3)	N11—C12—C13	112.9 (2)
C12—N11—C16	124.1 (3)	N13—C13—C12	118.5 (2)
O132—N13—C13	119.7 (3)	N13—C13—C14	119.1 (3)
O131—N13—O132	123.8 (4)	C12—C13—C14	122.4 (3)
O131—N13—C13	116.5 (3)	C13—C14—C15	120.4 (3)
O2—C2—N1	118.0 (2)	C14—C15—C16	118.6 (3)
O2—C2—C3	129.3 (2)	N11—C16—C15	121.6 (3)
N1—C2—C3	112.7 (2)	N11—C17—C18	110.8 (3)
N3—C3—C2	119.1 (2)	O18—C18—O19	124.7 (3)
N3—C3—C4	117.6 (2)	O18—C18—C17	124.8 (3)
C2—C3—C4	123.4 (2)	O19—C18—C17	110.5 (3)
C3—C4—C5	119.7 (2)	O19—C19—C20	108.2 (3)
C4—C5—C6	119.0 (2)	C13—C14—H14	120.00
N1—C6—C5	121.7 (2)	C15—C14—H14	120.00
N1—C7—C8	111.0 (2)	C14—C15—H15	121.00
O8—C8—C7	124.9 (3)	C16—C15—H15	121.00
O9—C8—C7	110.4 (2)	N11—C16—H16	119.00
O8—C8—O9	124.7 (3)	C15—C16—H16	119.00
O9—C9—C10	111.1 (3)	N11—C17—H171	109.00
C3—C4—H4	120.00	N11—C17—H172	109.00
C5—C4—H4	120.00	C18—C17—H171	109.00
C4—C5—H5	120.00	C18—C17—H172	109.00
C6—C5—H5	121.00	H171—C17—H172	110.00
N1—C6—H6	119.00	O19—C19—H191	110.00
C5—C6—H6	119.00	O19—C19—H192	110.00
N1—C7—H71	109.00	C20—C19—H191	110.00
C8—C7—H72	109.00	C20—C19—H192	110.00
N1—C7—H72	109.00	H191—C19—H192	110.00
C8—C7—H71	109.00	C19—C20—H201	109.00
H71—C7—H72	109.00	C19—C20—H202	109.00
C10—C9—H92	109.00	C19—C20—H203	109.00
O9—C9—H91	109.00	H201—C20—H202	110.00
O9—C9—H92	109.00	H201—C20—H203	110.00
C10—C9—H91	109.00	H202—C20—H203	110.00
C9—O9—C8—O8	0.3 (4)	C12—N11—C16—C15	−1.8 (4)
C9—O9—C8—C7	179.4 (3)	O132—N13—C13—C12	22.4 (4)
C8—O9—C9—C10	107.6 (4)	O131—N13—C13—C14	23.4 (4)
C18—O19—C19—C20	170.7 (3)	O132—N13—C13—C14	−156.0 (3)
C19—O19—C18—C17	175.3 (3)	O131—N13—C13—C12	−158.2 (3)
C19—O19—C18—O18	−4.5 (4)	O2—C2—C3—N3	−4.5 (4)
C7—N1—C2—C3	179.3 (2)	N1—C2—C3—C4	−3.0 (4)
C6—N1—C2—C3	2.0 (4)	N1—C2—C3—N3	177.1 (2)
C7—N1—C2—O2	0.8 (3)	O2—C2—C3—C4	175.4 (3)
C2—N1—C6—C5	−0.2 (4)	C2—C3—C4—C5	2.2 (4)
C6—N1—C2—O2	−176.6 (3)	N3—C3—C4—C5	−177.9 (3)
C6—N1—C7—C8	98.9 (3)	C3—C4—C5—C6	−0.1 (4)
C7—N1—C6—C5	−177.4 (3)	C4—C5—C6—N1	−0.9 (4)
C2—N1—C7—C8	−78.5 (3)	N1—C7—C8—O8	−23.6 (4)
O32—N3—C3—C2	−18.5 (4)	N1—C7—C8—O9	157.4 (2)
O31—N3—C3—C4	−16.6 (4)	O12—C12—C13—N13	1.9 (4)
O32—N3—C3—C4	161.6 (3)	O12—C12—C13—C14	−179.8 (3)
O31—N3—C3—C2	163.4 (3)	N11—C12—C13—C14	−1.6 (4)
C12—N11—C17—C18	−85.9 (3)	N11—C12—C13—N13	−179.9 (2)
C16—N11—C12—C13	2.6 (4)	C12—C13—C14—C15	−0.3 (5)
C17—N11—C12—C13	177.0 (2)	N13—C13—C14—C15	178.0 (3)
C16—N11—C12—O12	−179.0 (3)	C13—C14—C15—C16	1.3 (5)
C16—N11—C17—C18	88.8 (3)	C14—C15—C16—N11	−0.3 (5)
C17—N11—C16—C15	−176.1 (3)	N11—C17—C18—O18	−6.2 (4)
C17—N11—C12—O12	−4.6 (4)	N11—C17—C18—O19	174.1 (2)

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x, −y−1/2, z−1/2; (iii) x, −y+1/2, z−1/2; (iv) −x, y+1/2, −z+3/2; (v) x, y−1, z; (vi) x, −y−1/2, z+1/2; (vii) −x, −y−1, −z+1; (viii) x, y+1, z; (ix) x, −y+1/2, z+1/2; (x) −x+1, y+1/2, −z+3/2; (xi) −x, y−1/2, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2^vi	0.95	2.24	3.117 (3)	154
C5—H5···O32^vi	0.95	2.64	3.457 (4)	145
C16—H16···O12^vi	0.95	2.17	3.049 (4)	153
C17—H172···O132^vi	0.95	2.67	3.536 (4)	152
C9—H91···O8^x	0.95	2.57	3.517 (5)	173

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