(3RS)-2′-Amino-2,5′-dioxo-1,2-dihydro-5′H-spiro­[indole-3,4′-pyrano[3,2-c]chromene]-3′-carbonitrile

Zhu, S.-L.; Ji, S.-J.; Zhang, Y.

doi:10.1107/S1600536807034174

(3RS)-2′-Amino-2,5′-dioxo-1,2-dihydro-5′H-spiro[indole-3,4′-pyrano[3,2-c]chromene]-3′-carbonitrile

The title compound, C₂₀H₁₁N₃O₄, was synthesized by one-pot reaction of isatin, malononitrile and 4-hydroxycoumarin in water. In the title molecule, the angle between the pyran plane and the indole ring system with a common spiro C atom is 88.23 (8)°. The molecules are linked into a three-dimensional framework by the formation of moderate N—H

O and N—H

N hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807034174/fb2056sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807034174/fb2056Isup2.hkl Contains datablock I

CCDC reference: 299591

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R factor = 0.048
wR factor = 0.107
Data-to-parameter ratio = 12.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C3     = ...          S

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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

The indole nucleus is a well known heterocycle (da Silva et al., 2001). Compounds carrying the indole moiety exhibit antibacterial and fungicidal activities (Joshi & Chand, 1982). Spirooxindole ring systems are found in a number of alkaloids like horsifiline, spirotryprostatin and elacomine (Abdel-Rahman et al., 2004). As a part of our program devoted to the preparation of heterocyclic compounds involving indole derivatives (Wang et al., 2006), we have synthesized a series of spirooxindoles via reactions of substituted isatins together with malononitrile and 4-hydroxycoumarin in water. Herein we report the crystal structure of the title compound, (I) (Fig. 1).

In (I), the atoms of the pyran ring (C1/C2/C3/C4/C5/O1) are almost coplanar with the largest deviation of O1 being 0.067 (1) Å from the mean plane (Spek, 2003).

The angle between the pyran plane and the indole ring with a common spiro atom C3 is 88.23 (8)°.

The molecules are linked into a three-dimensional framework structure by the formation of the moderate N—H···O and N—H···N hydrogen bonds. The atom N3 donates a hydrogen H3B to the atom O4ⁱ [Symmetry code: (i) -x + 1/2, y + 1/2, -z + 1/2.] forming thus a graph set C(7) - (Fig. 2) (Bernstein et al., 1995). The adjacent chains are connected by the pairs of N1—H1···O2ⁱⁱ hydrogen bonds forming a sheet with a cyclic motif R₂²(14) (Fig. 3). [Symmetry code: (ii) -x + 1, -y, -z + 1.] The sheet is parallel to (001).

The sheets also interact via N3—H3A···N2ⁱⁱⁱ with a graph set R₂²(12), forming thus a three-dimensional network structure. [Symmetry code: (iii) -x + 1/2, -y + 1/2, -z + 1.]

Related literature top

For general background, see: Abdel-Rahman et al. (2004); da Silva et al. (2001); Joshi & Chand, (1982); Wang & Ji (2006).

For related literature, see: Bernstein et al. (1995); Spek (2003).

Experimental top

The title compound was prepared by the reaction of isatin (1 mmol), malononitrile (1 mmol) and 4-hydroxycoumarin (1 mmol) in water (5 ml). The reaction was catalyzed by TEBA (triethylbenzylammonium chloride, 1 mmol). After stirring at 333 K for 2 h, the reaction mixture was cooled and washed with small amount of ethanol. The crude product was filtered and single crystals of the title compound were obtained from 95% aqueous ethanol solution by slow evaporation at room temperature (yield 80%; m.p. 563–564 K). Spectroscopic analysis: IR (KBr, n, cm^-1): 3357, 3303, 3195, 2955, 2199, 1721, 1667, 1613, 1523, 1474, 1366, 1227, 1132, 1072, 972, 864, 748, 563 ¹H NMR (400 MHz, DMSO-d₆): 7.95 (d, 1H, J = 8.0 Hz, ArH), 7.77 (t, 1H, J = 7.6 Hz, ArH), 7.67 (br s, 2H, NH2), 7.57 (t, 1H, J = 7.6 Hz, ArH), 7.50 (d, 1H, J = 8.4 Hz, ArH), 7.22 (t, 2H, J = 7.6 Hz, ArH), 6.93 (t, 1H, J = 7.6 Hz, ArH), 6.85 (d, 1H, J = 8.0 Hz, ArH).

Structure description top

In (I), the atoms of the pyran ring (C1/C2/C3/C4/C5/O1) are almost coplanar with the largest deviation of O1 being 0.067 (1) Å from the mean plane (Spek, 2003).

The angle between the pyran plane and the indole ring with a common spiro atom C3 is 88.23 (8)°.

The sheets also interact via N3—H3A···N2ⁱⁱⁱ with a graph set R₂²(12), forming thus a three-dimensional network structure. [Symmetry code: (iii) -x + 1/2, -y + 1/2, -z + 1.]

For general background, see: Abdel-Rahman et al. (2004); da Silva et al. (2001); Joshi & Chand, (1982); Wang & Ji (2006).

For related literature, see: Bernstein et al. (1995); Spek (2003).

Computing details top

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. The molecular structure of the title structure, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. Part of the title crystal structure, showing the a (001) sheet with the N—H···O hydrogen bonds. For the sake of clarity, the H atoms bonded to C atoms have been omitted. O, N, C atoms are depicted in red, blue and black, respectively. [Symmetry codes: (i) -x + 1/2, y + 1/2, -z + 1/2; (ii) -x + 1, -y, -z + 1.]
	Fig. 3. Part of the title crystal structure, showing a cyclic motif R₂²(14) of the N1—H1···O2ⁱⁱ hydrogen bond pattern. O, N, C atoms are depicted in red, blue and black, respectively. [Symmetry code: (ii) -x + 1, -y, -z + 1.]

(3RS)-2'-Amino-2,5'-dioxo-1,2-dihydro-5'H-spiro[indole-3,4'- pyrano[3,2-c]chromene]-3'-carbonitrile top

Crystal data top

C₂₀H₁₁N₃O₄	F(000) = 1472
M_r = 357.32	D_x = 1.416 Mg m⁻³
Monoclinic, C2/c	Melting point = 563–564 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 25.265 (4) Å	Cell parameters from 5284 reflections
b = 11.0076 (12) Å	θ = 3.0–25.3°
c = 14.864 (2) Å	µ = 0.10 mm⁻¹
β = 125.820 (3)°	T = 173 K
V = 3351.9 (8) Å³	Block, colourless
Z = 8	0.31 × 0.30 × 0.20 mm

Data collection top

Rigaku Mercury diffractometer	3068 independent reflections
Radiation source: fine-focus sealed tube	2674 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.4°, θ_min = 3.0°
ω scans	h = −30→30
Absorption correction: multi-scan (Jacobson, 1998)	k = −13→12
T_min = 0.969, T_max = 0.980	l = −17→17
16029 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.107	w = 1/[σ²(F_o²) + (0.0419P)² + 2.3453P] where P = (F_o² + 2F_c²)/3
S = 1.15	(Δ/σ)_max < 0.001
3068 reflections	Δρ_max = 0.20 e Å⁻³
255 parameters	Δρ_min = −0.22 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
35 constraints	Extinction coefficient: 0.0011 (2)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₂₀H₁₁N₃O₄	V = 3351.9 (8) Å³
M_r = 357.32	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 25.265 (4) Å	µ = 0.10 mm⁻¹
b = 11.0076 (12) Å	T = 173 K
c = 14.864 (2) Å	0.31 × 0.30 × 0.20 mm
β = 125.820 (3)°

Data collection top

Rigaku Mercury diffractometer	3068 independent reflections
Absorption correction: multi-scan (Jacobson, 1998)	2674 reflections with I > 2σ(I)
T_min = 0.969, T_max = 0.980	R_int = 0.035
16029 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	Δρ_max = 0.20 e Å⁻³
3068 reflections	Δρ_min = −0.22 e Å⁻³
255 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	0.27661 (6)	0.34373 (11)	0.22134 (10)	0.0312 (3)
O2	0.48118 (6)	0.16044 (12)	0.36788 (11)	0.0377 (4)
O3	0.42608 (6)	0.24176 (13)	0.20112 (11)	0.0383 (3)
O4	0.37375 (6)	−0.00143 (12)	0.37643 (11)	0.0392 (4)
N1	0.46001 (7)	0.07244 (14)	0.54446 (12)	0.0292 (4)
H1	0.4763 (9)	0.0014 (19)	0.5746 (17)	0.035*
N2	0.31587 (8)	0.17282 (17)	0.55027 (14)	0.0411 (4)
N3	0.21451 (7)	0.32125 (16)	0.28103 (14)	0.0337 (4)
H3A	0.2087 (10)	0.3088 (19)	0.3354 (19)	0.040*
H3B	0.1874 (10)	0.369 (2)	0.2224 (18)	0.040*
C1	0.32893 (8)	0.31103 (16)	0.22205 (15)	0.0274 (4)
C2	0.38132 (8)	0.25213 (16)	0.30683 (14)	0.0267 (4)
C3	0.38915 (8)	0.21902 (15)	0.41237 (14)	0.0254 (4)
C4	0.32491 (8)	0.24481 (16)	0.39560 (14)	0.0267 (4)
C5	0.27354 (8)	0.30078 (16)	0.30509 (14)	0.0275 (4)
C6	0.43259 (9)	0.21535 (16)	0.29663 (15)	0.0302 (4)
C7	0.37258 (9)	0.30335 (17)	0.11484 (15)	0.0331 (4)
C8	0.37033 (10)	0.32238 (19)	0.02064 (17)	0.0407 (5)
H8	0.4044	0.2945	0.0165	0.049*
C9	0.31716 (11)	0.38302 (19)	−0.06707 (17)	0.0433 (5)
H9	0.3148	0.3971	−0.1324	0.052*
C10	0.26699 (10)	0.42402 (19)	−0.06187 (17)	0.0423 (5)
H10	0.2308	0.4657	−0.1233	0.051*
C11	0.26960 (9)	0.40437 (18)	0.03233 (15)	0.0365 (5)
H11	0.2354	0.4326	0.0360	0.044*
C12	0.32293 (9)	0.34260 (16)	0.12260 (14)	0.0301 (4)
C13	0.40581 (8)	0.08170 (16)	0.43953 (15)	0.0281 (4)
C14	0.48718 (8)	0.18667 (16)	0.59080 (15)	0.0287 (4)
C15	0.54420 (9)	0.21274 (19)	0.69336 (16)	0.0370 (5)
H15	0.5713	0.1499	0.7432	0.044*
C16	0.56031 (10)	0.3339 (2)	0.72057 (17)	0.0435 (5)
H16	0.5991	0.3547	0.7905	0.052*
C17	0.52090 (10)	0.42502 (19)	0.64776 (17)	0.0428 (5)
H17	0.5328	0.5075	0.6687	0.051*
C18	0.46399 (9)	0.39779 (17)	0.54424 (16)	0.0342 (4)
H18	0.4371	0.4605	0.4940	0.041*
C19	0.44769 (8)	0.27733 (16)	0.51654 (14)	0.0258 (4)
C20	0.31907 (8)	0.20584 (17)	0.47984 (15)	0.0299 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0286 (7)	0.0382 (8)	0.0272 (6)	0.0093 (5)	0.0166 (6)	0.0074 (6)
O2	0.0327 (7)	0.0409 (8)	0.0439 (8)	0.0105 (6)	0.0248 (7)	0.0131 (6)
O3	0.0372 (8)	0.0490 (8)	0.0364 (8)	0.0095 (6)	0.0259 (7)	0.0107 (6)
O4	0.0398 (8)	0.0314 (7)	0.0386 (8)	−0.0057 (6)	0.0185 (7)	−0.0072 (6)
N1	0.0286 (8)	0.0256 (8)	0.0289 (8)	0.0044 (6)	0.0142 (7)	0.0056 (7)
N2	0.0298 (9)	0.0597 (12)	0.0331 (9)	0.0053 (8)	0.0181 (8)	0.0090 (8)
N3	0.0268 (8)	0.0467 (10)	0.0262 (8)	0.0111 (7)	0.0147 (7)	0.0074 (8)
C1	0.0262 (9)	0.0274 (9)	0.0278 (9)	0.0010 (7)	0.0154 (8)	0.0003 (8)
C2	0.0267 (9)	0.0258 (9)	0.0268 (9)	−0.0001 (7)	0.0152 (8)	0.0011 (7)
C3	0.0225 (9)	0.0266 (9)	0.0252 (9)	0.0020 (7)	0.0129 (7)	0.0018 (7)
C4	0.0242 (9)	0.0303 (10)	0.0241 (9)	0.0023 (7)	0.0133 (8)	0.0011 (7)
C5	0.0271 (9)	0.0310 (10)	0.0239 (9)	0.0011 (7)	0.0146 (8)	−0.0023 (7)
C6	0.0310 (10)	0.0296 (10)	0.0330 (10)	0.0011 (8)	0.0203 (9)	0.0032 (8)
C7	0.0343 (10)	0.0341 (10)	0.0302 (10)	−0.0011 (8)	0.0184 (8)	0.0021 (8)
C8	0.0469 (12)	0.0455 (12)	0.0393 (11)	−0.0030 (10)	0.0306 (10)	0.0017 (10)
C9	0.0580 (13)	0.0429 (12)	0.0324 (11)	−0.0093 (10)	0.0283 (10)	0.0014 (9)
C10	0.0499 (12)	0.0372 (12)	0.0320 (11)	−0.0015 (9)	0.0196 (10)	0.0082 (9)
C11	0.0382 (11)	0.0341 (11)	0.0329 (10)	0.0003 (8)	0.0184 (9)	0.0039 (9)
C12	0.0334 (10)	0.0292 (10)	0.0265 (9)	−0.0015 (8)	0.0169 (8)	0.0022 (8)
C13	0.0280 (9)	0.0299 (10)	0.0294 (9)	−0.0008 (8)	0.0186 (8)	−0.0004 (8)
C14	0.0244 (9)	0.0333 (10)	0.0287 (9)	0.0023 (7)	0.0156 (8)	0.0012 (8)
C15	0.0258 (10)	0.0473 (12)	0.0291 (10)	0.0026 (8)	0.0112 (8)	0.0022 (9)
C16	0.0314 (11)	0.0545 (14)	0.0329 (11)	−0.0094 (9)	0.0122 (9)	−0.0074 (10)
C17	0.0438 (12)	0.0385 (12)	0.0433 (12)	−0.0128 (9)	0.0238 (10)	−0.0089 (10)
C18	0.0352 (10)	0.0308 (10)	0.0367 (10)	−0.0016 (8)	0.0210 (9)	0.0005 (9)
C19	0.0244 (9)	0.0288 (9)	0.0252 (9)	0.0002 (7)	0.0151 (8)	0.0008 (7)
C20	0.0197 (9)	0.0376 (11)	0.0281 (10)	0.0023 (7)	0.0116 (8)	0.0016 (8)

Geometric parameters (Å, º) top

O1—C1	1.364 (2)	C4—C20	1.411 (3)
O1—C5	1.375 (2)	C7—C8	1.384 (3)
O2—C6	1.213 (2)	C7—C12	1.394 (3)
O3—C6	1.361 (2)	C8—C9	1.378 (3)
O3—C7	1.379 (2)	C8—H8	0.9500
O4—C13	1.218 (2)	C9—C10	1.390 (3)
N1—C13	1.348 (2)	C9—H9	0.9500
N1—C14	1.405 (2)	C10—C11	1.380 (3)
N1—H1	0.88 (2)	C10—H10	0.9500
N2—C20	1.155 (2)	C11—C12	1.401 (3)
N3—C5	1.334 (2)	C11—H11	0.9500
N3—H3A	0.91 (2)	C14—C15	1.382 (3)
N3—H3B	0.90 (2)	C14—C19	1.386 (2)
C1—C2	1.345 (2)	C15—C16	1.384 (3)
C1—C12	1.438 (2)	C15—H15	0.9500
C2—C6	1.447 (2)	C16—C17	1.381 (3)
C2—C3	1.507 (2)	C16—H16	0.9500
C3—C4	1.518 (2)	C17—C18	1.391 (3)
C3—C19	1.522 (2)	C17—H17	0.9500
C3—C13	1.558 (2)	C18—C19	1.378 (3)
C4—C5	1.353 (2)	C18—H18	0.9500

C1—O1—C5	118.03 (13)	C8—C9—C10	121.36 (19)
C6—O3—C7	121.95 (14)	C8—C9—H9	119.3
C13—N1—C14	111.93 (15)	C10—C9—H9	119.3
C13—N1—H1	120.9 (13)	C11—C10—C9	120.14 (19)
C14—N1—H1	126.9 (13)	C11—C10—H10	119.9
C5—N3—H3A	118.2 (13)	C9—C10—H10	119.9
C5—N3—H3B	117.1 (13)	C10—C11—C12	119.74 (19)
H3A—N3—H3B	121.4 (19)	C10—C11—H11	120.1
C2—C1—O1	123.54 (16)	C12—C11—H11	120.1
C2—C1—C12	122.25 (16)	C7—C12—C11	118.61 (17)
O1—C1—C12	114.19 (15)	C7—C12—C1	116.86 (16)
C1—C2—C6	119.16 (16)	C11—C12—C1	124.45 (17)
C1—C2—C3	123.35 (16)	O4—C13—N1	126.97 (17)
C6—C2—C3	117.47 (15)	O4—C13—C3	124.92 (16)
C2—C3—C4	107.92 (14)	N1—C13—C3	108.10 (15)
C2—C3—C19	114.49 (14)	C15—C14—C19	121.91 (18)
C4—C3—C19	113.41 (14)	C15—C14—N1	128.42 (17)
C2—C3—C13	110.83 (14)	C19—C14—N1	109.67 (15)
C4—C3—C13	108.96 (14)	C14—C15—C16	117.44 (18)
C19—C3—C13	101.03 (13)	C14—C15—H15	121.3
C5—C4—C20	118.91 (16)	C16—C15—H15	121.3
C5—C4—C3	124.04 (16)	C17—C16—C15	121.13 (18)
C20—C4—C3	117.04 (15)	C17—C16—H16	119.4
N3—C5—C4	127.95 (17)	C15—C16—H16	119.4
N3—C5—O1	110.22 (15)	C16—C17—C18	120.98 (19)
C4—C5—O1	121.82 (15)	C16—C17—H17	119.5
O2—C6—O3	117.36 (16)	C18—C17—H17	119.5
O2—C6—C2	123.94 (17)	C19—C18—C17	118.20 (18)
O3—C6—C2	118.69 (15)	C19—C18—H18	120.9
O3—C7—C8	116.93 (17)	C17—C18—H18	120.9
O3—C7—C12	121.00 (16)	C18—C19—C14	120.33 (17)
C8—C7—C12	122.07 (18)	C18—C19—C3	130.72 (16)
C9—C8—C7	118.07 (19)	C14—C19—C3	108.94 (15)
C9—C8—H8	121.0	N2—C20—C4	178.28 (19)
C7—C8—H8	121.0

C5—O1—C1—C2	−8.6 (2)	O3—C7—C12—C11	−179.78 (17)
C5—O1—C1—C12	170.11 (15)	C8—C7—C12—C11	−0.7 (3)
O1—C1—C2—C6	176.44 (16)	O3—C7—C12—C1	−2.7 (3)
C12—C1—C2—C6	−2.1 (3)	C8—C7—C12—C1	176.34 (18)
O1—C1—C2—C3	−2.0 (3)	C10—C11—C12—C7	0.6 (3)
C12—C1—C2—C3	179.40 (16)	C10—C11—C12—C1	−176.26 (18)
C1—C2—C3—C4	9.1 (2)	C2—C1—C12—C7	3.5 (3)
C6—C2—C3—C4	−169.42 (15)	O1—C1—C12—C7	−175.24 (15)
C1—C2—C3—C19	−118.24 (19)	C2—C1—C12—C11	−179.66 (18)
C6—C2—C3—C19	63.3 (2)	O1—C1—C12—C11	1.6 (3)
C1—C2—C3—C13	128.30 (18)	C14—N1—C13—O4	175.88 (18)
C6—C2—C3—C13	−50.2 (2)	C14—N1—C13—C3	−5.80 (19)
C2—C3—C4—C5	−6.8 (2)	C2—C3—C13—O4	−54.4 (2)
C19—C3—C4—C5	121.10 (19)	C4—C3—C13—O4	64.2 (2)
C13—C3—C4—C5	−127.24 (18)	C19—C3—C13—O4	−176.12 (17)
C2—C3—C4—C20	172.28 (16)	C2—C3—C13—N1	127.26 (15)
C19—C3—C4—C20	−59.8 (2)	C4—C3—C13—N1	−114.14 (15)
C13—C3—C4—C20	51.9 (2)	C19—C3—C13—N1	5.52 (18)
C20—C4—C5—N3	−2.9 (3)	C13—N1—C14—C15	−176.13 (18)
C3—C4—C5—N3	176.17 (17)	C13—N1—C14—C19	3.6 (2)
C20—C4—C5—O1	178.32 (16)	C19—C14—C15—C16	1.0 (3)
C3—C4—C5—O1	−2.6 (3)	N1—C14—C15—C16	−179.36 (18)
C1—O1—C5—N3	−168.19 (15)	C14—C15—C16—C17	−0.1 (3)
C1—O1—C5—C4	10.8 (2)	C15—C16—C17—C18	−0.6 (3)
C7—O3—C6—O2	179.72 (16)	C16—C17—C18—C19	0.5 (3)
C7—O3—C6—C2	0.7 (3)	C17—C18—C19—C14	0.3 (3)
C1—C2—C6—O2	−178.94 (18)	C17—C18—C19—C3	178.86 (18)
C3—C2—C6—O2	−0.4 (3)	C15—C14—C19—C18	−1.1 (3)
C1—C2—C6—O3	0.0 (3)	N1—C14—C19—C18	179.20 (16)
C3—C2—C6—O3	178.58 (15)	C15—C14—C19—C3	−179.91 (16)
C6—O3—C7—C8	−178.35 (17)	N1—C14—C19—C3	0.4 (2)
C6—O3—C7—C12	0.8 (3)	C2—C3—C19—C18	58.7 (2)
O3—C7—C8—C9	179.59 (17)	C4—C3—C19—C18	−65.7 (2)
C12—C7—C8—C9	0.5 (3)	C13—C3—C19—C18	177.87 (18)
C7—C8—C9—C10	−0.1 (3)	C2—C3—C19—C14	−122.58 (16)
C8—C9—C10—C11	0.0 (3)	C4—C3—C19—C14	112.97 (17)
C9—C10—C11—C12	−0.2 (3)	C13—C3—C19—C14	−3.45 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O4ⁱ	0.90 (2)	1.98 (2)	2.855 (2)	164.2 (19)
N1—H1···O2ⁱⁱ	0.88 (2)	2.00 (2)	2.865 (2)	172.2 (19)
N3—H3A···N2ⁱⁱⁱ	0.91 (2)	2.13 (2)	3.022 (2)	164.7 (18)

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₁N₃O₄
M_r	357.32
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	173
a, b, c (Å)	25.265 (4), 11.0076 (12), 14.864 (2)
β (°)	125.820 (3)
V (Å³)	3351.9 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.31 × 0.30 × 0.20

Data collection
Diffractometer	Rigaku Mercury
Absorption correction	Multi-scan (Jacobson, 1998)
T_min, T_max	0.969, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	16029, 3068, 2674
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.107, 1.15
No. of reflections	3068
No. of parameters	255
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.22

Computer programs: CrystalClear (Molecular Structure Corporation & Rigaku, 2001), CrystalClear, CrystalStructure (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97.