4,4′-Dinitro-2,2′-[propane-1,3-diylbis(iminiumylmethanylyl­idene)]diphenolate

Ha, K.

doi:10.1107/S1600536812015504

organic compounds

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Volume 68| Part 5| May 2012| Page o1399

doi:10.1107/S1600536812015504

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4,4′-Dinitro-2,2′-[propane-1,3-diylbis(iminiumylmethanylylidene)]diphenolate

Kwang Ha ^a ^*

^aSchool of Applied Chemical Engineering, The Research Institute of Catalysis, Chonnam National University, Gwangju 500-757, Republic of Korea
^*Correspondence e-mail: hakwang@chonnam.ac.kr

(Received 10 April 2012; accepted 10 April 2012; online 18 April 2012)

The title compound, C₁₇H₁₆N₄O₆, is a Schiff base, which is found as a bis-zwitterion in the solid state. The geometry around the iminium N atom indicates sp²-hybridization. The diiminiumpropylene chain is in an approximate double-gauche conformation, with average N—C—C—C torsion angles of 69.3°. The zwitterion shows strong intramolecular N—H⋯O hydrogen bonds between the iminium N and phenolate O atom. In the crystal, bifurcated N—H⋯(O,O) hydrogen bonds assemble pairs of molecules into inversion dimers.

Related literature

For the crystal structure of the related zwitterion, 4-nitro-2-{[(tricyclo[3.3.1.1^3,7]decan-1-yl)iminiumyl]methyl}phenolate, see: Ha (2012 ).

Experimental

Crystal data

C₁₇H₁₆N₄O₆
M_r = 372.34
Orthorhombic, P b c a
a = 11.5698 (5) Å
b = 13.0393 (6) Å
c = 22.0393 (10) Å
V = 3324.9 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 200 K
0.31 × 0.17 × 0.15 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.890, T_max = 1.000
23432 measured reflections
4120 independent reflections
2286 reflections with I > 2σ(I)
R_int = 0.084

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.138
S = 1.03
4120 reflections
252 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H3N⋯O1	0.93 (3)	1.77 (3)	2.583 (2)	145 (3)
N3—H2N⋯O4	0.90 (3)	1.93 (3)	2.642 (2)	135 (2)
N3—H2N⋯O4ⁱ	0.90 (3)	2.17 (3)	2.891 (2)	136 (2)
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812015504/zl2472sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812015504/zl2472Isup2.hkl

checkCIF report

Comment top

The title compound, C₁₇H₁₆N₄O₆, is a tetradentate Schiff base, which can act as a dibasic ligand, that is, the N₂O₂ donor atoms can coordinate to a metal ion. In the crystal structure, the Schiff base is found as a bis(zwitterion) in the phenolate-iminium forms (Fig. 1), similar to the structure of the related zwitterion 4-nitro-2-{[(tricyclo[3.3.1.1^3,7]decan-1-yl)iminiumyl]methyl}phenolate (Ha, 2012). It seems that the acid strength of the phenol was reinforced by the inductive effects of the electron-withdrawing NO₂ group.

The N—C bond lengths and the C—N—C bond angles indicate that the iminium N atoms are sp²-hybridized [N2═C7 = 1.292 (2) Å, N2—C8 = 1.456 (3) Å, <C7—N2—C8 = 125.25 (19)°; N3═C11 = 1.293 (3) Å, N3—C10 = 1.457 (3) Å, <C11—N3—C10 = 124.97 (18)°]. The dihedral angles for the four atoms within the diiminiumpropylene chain display that the chain is approximately in the double gauche conformation [<N2—C8—C9—C10 = 69.6 (2)° and <C8—C9—C10—N3 = 69.0 (2)°]. The zwitterion shows strong intramolecular N—H···O hydrogen bonds between the iminium N atom and the phenolate O atom, with N···O distances of 2.583 (2) Å and 2.642 (2) Å, forming nearly planar six-membered rings (Fig. 2, Table 1). Two ions are assembled by additional intermolecular N—H···O hydrogen bonds with N···O = 2.891 (2) Å, forming a dimer-type species (Fig. 2, Table 1). In the crystal structure, the benzene rings are not parallel, the dihedral angle between the rings being 11.45 (2)°. Several π-π interactions between the adjacent benzene rings are present, the shortest centroid-centroid distance being 3.5432 (11) Å.

Related literature top

For the crystal structure of the related zwitterion, 4-nitro-2-{[(tricyclo[3.3.1.1^3,7]decan-1-yl)iminiumyl]methyl}phenolate, see: Ha (2012).

Experimental top

1,3-Diaminopropane (0.3704 g, 5.00 mmol) and 5-nitrosalicylaldehyde (1.6719 g, 10.00 mmol) in EtOH (20 ml) were stirred for 2 h at room temparature. After addition of pentane (30 ml) to the reaction mixture, the formed precipitate was separated by filtration, washed with ether (50 ml), and dried at 323 K, to give a yellow powder (1.8169 g). Yellow block-like crystals, suitable for X-ray analysis, were obtained by slow evaporation of a CH₃CN solution at room temparature.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom numbering. Displacement ellipsoids are drawn at the 50% probability level for non-H atoms.
	Fig. 2. A partial view along the b axis of the crystal packing of the title compound. Intra- and intermolecular N—H···O hydrogen-bonds are shown as dashed lines (see Table 1 for details).

4,4'-Dinitro-2,2'-[propane-1,3-diylbis(iminiumylmethanylylidene)]diphenolate top

Crystal data top

C₁₇H₁₆N₄O₆	F(000) = 1552
M_r = 372.34	D_x = 1.488 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3572 reflections
a = 11.5698 (5) Å	θ = 2.5–25.3°
b = 13.0393 (6) Å	µ = 0.12 mm⁻¹
c = 22.0393 (10) Å	T = 200 K
V = 3324.9 (3) Å³	Block, yellow
Z = 8	0.31 × 0.17 × 0.15 mm

Data collection top

Bruker SMART 1000 CCD diffractometer	4120 independent reflections
Radiation source: fine-focus sealed tube	2286 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.084
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −15→15
T_min = 0.890, T_max = 1.000	k = −14→17
23432 measured reflections	l = −28→29

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0572P)² + 0.0212P] where P = (F_o² + 2F_c²)/3
4120 reflections	(Δ/σ)_max < 0.001
252 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₇H₁₆N₄O₆	V = 3324.9 (3) Å³
M_r = 372.34	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 11.5698 (5) Å	µ = 0.12 mm⁻¹
b = 13.0393 (6) Å	T = 200 K
c = 22.0393 (10) Å	0.31 × 0.17 × 0.15 mm

Data collection top

Bruker SMART 1000 CCD diffractometer	4120 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2286 reflections with I > 2σ(I)
T_min = 0.890, T_max = 1.000	R_int = 0.084
23432 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.28 e Å⁻³
4120 reflections	Δρ_min = −0.30 e Å⁻³
252 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	0.18305 (12)	0.22185 (11)	0.21082 (6)	0.0397 (4)
O2	0.63010 (14)	0.28176 (13)	0.05617 (7)	0.0495 (4)
O3	0.50263 (15)	0.25797 (13)	−0.01460 (7)	0.0522 (5)
O4	0.62220 (12)	−0.00556 (11)	0.48734 (6)	0.0383 (4)
O5	0.96696 (14)	−0.02327 (15)	0.27155 (8)	0.0636 (5)
O6	1.08562 (13)	−0.02659 (13)	0.34711 (8)	0.0536 (5)
N1	0.52991 (16)	0.26527 (13)	0.03929 (9)	0.0372 (4)
N2	0.34001 (16)	0.22765 (13)	0.29410 (8)	0.0325 (4)
H2N	0.491 (2)	0.0128 (18)	0.4342 (13)	0.061 (8)*
N3	0.48198 (14)	0.01663 (13)	0.39362 (9)	0.0300 (4)
H3N	0.266 (3)	0.2203 (19)	0.2781 (13)	0.079 (9)*
N4	0.98619 (16)	−0.02418 (14)	0.32658 (9)	0.0388 (5)
C1	0.26324 (17)	0.23326 (14)	0.17156 (9)	0.0293 (5)
C2	0.23969 (18)	0.23465 (14)	0.10807 (9)	0.0321 (5)
H2	0.1619	0.2290	0.0947	0.038*
C3	0.32499 (18)	0.24381 (14)	0.06613 (9)	0.0320 (5)
H3	0.3065	0.2433	0.0241	0.038*
C4	0.44063 (18)	0.25404 (14)	0.08474 (9)	0.0296 (5)
C5	0.46937 (17)	0.25358 (14)	0.14490 (9)	0.0294 (5)
H5	0.5479	0.2608	0.1567	0.035*
C6	0.38325 (17)	0.24253 (14)	0.18915 (9)	0.0270 (4)
C7	0.41546 (18)	0.23887 (14)	0.25139 (9)	0.0305 (5)
H7	0.4948	0.2449	0.2619	0.037*
C8	0.36602 (19)	0.22306 (16)	0.35868 (9)	0.0349 (5)
H8A	0.3365	0.2858	0.3787	0.042*
H8B	0.4508	0.2208	0.3644	0.042*
C9	0.31172 (18)	0.12934 (15)	0.38808 (9)	0.0330 (5)
H9A	0.2285	0.1280	0.3777	0.040*
H9B	0.3179	0.1364	0.4327	0.040*
C10	0.36533 (17)	0.02741 (15)	0.36953 (9)	0.0320 (5)
H10A	0.3166	−0.0295	0.3847	0.038*
H10B	0.3678	0.0229	0.3247	0.038*
C11	0.57442 (17)	0.00744 (14)	0.36110 (9)	0.0274 (4)
H11	0.5665	0.0098	0.3182	0.033*
C12	0.68702 (17)	−0.00597 (14)	0.38544 (8)	0.0261 (4)
C13	0.70501 (18)	−0.01066 (14)	0.45046 (9)	0.0281 (4)
C14	0.82265 (18)	−0.02299 (16)	0.47050 (9)	0.0353 (5)
H14	0.8382	−0.0277	0.5127	0.042*
C15	0.91170 (18)	−0.02810 (16)	0.43079 (9)	0.0347 (5)
H15	0.9885	−0.0358	0.4453	0.042*
C16	0.89073 (17)	−0.02195 (15)	0.36768 (9)	0.0293 (4)
C17	0.78028 (17)	−0.01169 (14)	0.34546 (9)	0.0293 (5)
H17	0.7675	−0.0085	0.3029	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0255 (8)	0.0574 (10)	0.0362 (9)	−0.0014 (7)	0.0025 (7)	0.0090 (7)
O2	0.0335 (9)	0.0701 (12)	0.0450 (10)	0.0044 (8)	0.0064 (8)	0.0105 (8)
O3	0.0570 (11)	0.0726 (12)	0.0269 (9)	0.0072 (8)	0.0058 (8)	−0.0012 (7)
O4	0.0334 (8)	0.0565 (10)	0.0250 (8)	0.0030 (7)	0.0042 (7)	0.0031 (6)
O5	0.0469 (11)	0.1112 (16)	0.0326 (10)	0.0119 (10)	0.0109 (8)	0.0110 (9)
O6	0.0278 (9)	0.0770 (13)	0.0560 (11)	0.0016 (8)	0.0043 (8)	0.0064 (9)
N1	0.0380 (11)	0.0407 (11)	0.0330 (11)	0.0072 (8)	0.0040 (9)	0.0031 (8)
N2	0.0311 (10)	0.0420 (11)	0.0243 (10)	0.0018 (8)	−0.0008 (8)	0.0051 (7)
N3	0.0304 (10)	0.0370 (10)	0.0225 (10)	0.0030 (7)	−0.0016 (8)	−0.0009 (7)
N4	0.0323 (11)	0.0474 (12)	0.0367 (11)	0.0026 (8)	0.0050 (9)	0.0073 (8)
C1	0.0265 (11)	0.0295 (11)	0.0318 (11)	−0.0006 (8)	−0.0022 (9)	0.0047 (8)
C2	0.0304 (11)	0.0321 (12)	0.0336 (12)	−0.0020 (9)	−0.0048 (9)	0.0041 (9)
C3	0.0391 (13)	0.0284 (11)	0.0285 (11)	−0.0002 (9)	−0.0043 (9)	0.0018 (8)
C4	0.0306 (12)	0.0312 (11)	0.0271 (11)	0.0023 (9)	0.0029 (9)	0.0029 (8)
C5	0.0241 (10)	0.0316 (12)	0.0324 (12)	0.0015 (8)	−0.0017 (9)	0.0024 (8)
C6	0.0260 (10)	0.0279 (11)	0.0272 (11)	0.0023 (8)	−0.0019 (9)	0.0040 (8)
C7	0.0285 (11)	0.0314 (11)	0.0315 (11)	0.0009 (9)	0.0011 (9)	0.0022 (8)
C8	0.0368 (12)	0.0418 (13)	0.0260 (12)	0.0022 (10)	−0.0015 (9)	0.0002 (9)
C9	0.0315 (12)	0.0400 (13)	0.0274 (11)	0.0029 (9)	0.0019 (9)	0.0022 (9)
C10	0.0278 (11)	0.0425 (13)	0.0256 (11)	0.0015 (9)	−0.0017 (9)	0.0013 (9)
C11	0.0324 (11)	0.0280 (11)	0.0218 (10)	0.0010 (8)	−0.0012 (9)	−0.0004 (8)
C12	0.0288 (11)	0.0263 (11)	0.0233 (10)	0.0014 (8)	−0.0002 (8)	0.0009 (7)
C13	0.0317 (11)	0.0276 (11)	0.0251 (11)	−0.0018 (8)	0.0004 (9)	0.0010 (8)
C14	0.0331 (12)	0.0469 (13)	0.0260 (11)	−0.0042 (10)	−0.0033 (9)	0.0041 (9)
C15	0.0284 (11)	0.0414 (13)	0.0344 (13)	−0.0037 (10)	−0.0029 (9)	0.0040 (9)
C16	0.0300 (11)	0.0306 (11)	0.0274 (11)	−0.0010 (8)	0.0036 (9)	0.0036 (8)
C17	0.0346 (12)	0.0297 (11)	0.0236 (10)	−0.0003 (9)	0.0011 (9)	0.0015 (8)

Geometric parameters (Å, º) top

O1—C1	1.277 (2)	C5—H5	0.9500
O2—N1	1.236 (2)	C6—C7	1.422 (3)
O3—N1	1.233 (2)	C7—H7	0.9500
O4—C13	1.258 (2)	C8—C9	1.519 (3)
O5—N4	1.233 (2)	C8—H8A	0.9900
O6—N4	1.237 (2)	C8—H8B	0.9900
N1—C4	1.446 (3)	C9—C10	1.523 (3)
N2—C7	1.292 (2)	C9—H9A	0.9900
N2—C8	1.456 (3)	C9—H9B	0.9900
N2—H3N	0.93 (3)	C10—H10A	0.9900
N3—C11	1.293 (3)	C10—H10B	0.9900
N3—C10	1.457 (3)	C11—C12	1.420 (3)
N3—H2N	0.90 (3)	C11—H11	0.9500
N4—C16	1.429 (3)	C12—C17	1.395 (3)
C1—C2	1.426 (3)	C12—C13	1.449 (3)
C1—C6	1.447 (3)	C13—C14	1.440 (3)
C2—C3	1.357 (3)	C14—C15	1.353 (3)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.406 (3)	C15—C16	1.414 (3)
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.367 (3)	C16—C17	1.375 (3)
C5—C6	1.402 (3)	C17—H17	0.9500

O3—N1—O2	122.92 (18)	N2—C8—H8B	109.4
O3—N1—C4	118.46 (18)	C9—C8—H8B	109.4
O2—N1—C4	118.62 (18)	H8A—C8—H8B	108.0
C7—N2—C8	125.25 (19)	C8—C9—C10	114.79 (17)
C7—N2—H3N	110.9 (18)	C8—C9—H9A	108.6
C8—N2—H3N	123.8 (18)	C10—C9—H9A	108.6
C11—N3—C10	124.97 (18)	C8—C9—H9B	108.6
C11—N3—H2N	116.4 (16)	C10—C9—H9B	108.6
C10—N3—H2N	118.5 (16)	H9A—C9—H9B	107.5
O5—N4—O6	121.87 (18)	N3—C10—C9	111.32 (17)
O5—N4—C16	118.95 (18)	N3—C10—H10A	109.4
O6—N4—C16	119.19 (19)	C9—C10—H10A	109.4
O1—C1—C2	121.84 (18)	N3—C10—H10B	109.4
O1—C1—C6	121.70 (18)	C9—C10—H10B	109.4
C2—C1—C6	116.44 (18)	H10A—C10—H10B	108.0
C3—C2—C1	122.04 (19)	N3—C11—C12	124.13 (18)
C3—C2—H2	119.0	N3—C11—H11	117.9
C1—C2—H2	119.0	C12—C11—H11	117.9
C2—C3—C4	120.12 (19)	C17—C12—C11	118.54 (17)
C2—C3—H3	119.9	C17—C12—C13	120.74 (18)
C4—C3—H3	119.9	C11—C12—C13	120.70 (17)
C5—C4—C3	120.94 (19)	O4—C13—C14	121.84 (18)
C5—C4—N1	119.89 (19)	O4—C13—C12	121.81 (18)
C3—C4—N1	119.17 (18)	C14—C13—C12	116.34 (18)
C4—C5—C6	120.15 (18)	C15—C14—C13	121.78 (19)
C4—C5—H5	119.9	C15—C14—H14	119.1
C6—C5—H5	119.9	C13—C14—H14	119.1
C5—C6—C7	119.23 (18)	C14—C15—C16	120.17 (19)
C5—C6—C1	120.30 (18)	C14—C15—H15	119.9
C7—C6—C1	120.47 (18)	C16—C15—H15	119.9
N2—C7—C6	121.97 (19)	C17—C16—C15	121.02 (18)
N2—C7—H7	119.0	C17—C16—N4	119.63 (18)
C6—C7—H7	119.0	C15—C16—N4	119.33 (18)
N2—C8—C9	111.38 (17)	C16—C17—C12	119.93 (18)
N2—C8—H8A	109.4	C16—C17—H17	120.0
C9—C8—H8A	109.4	C12—C17—H17	120.0

O1—C1—C2—C3	−178.08 (18)	C11—N3—C10—C9	−118.0 (2)
C6—C1—C2—C3	0.2 (3)	C8—C9—C10—N3	69.0 (2)
C1—C2—C3—C4	−1.1 (3)	C10—N3—C11—C12	−178.09 (18)
C2—C3—C4—C5	0.9 (3)	N3—C11—C12—C17	−178.00 (18)
C2—C3—C4—N1	−179.06 (17)	N3—C11—C12—C13	0.3 (3)
O3—N1—C4—C5	174.81 (18)	C17—C12—C13—O4	179.94 (17)
O2—N1—C4—C5	−5.2 (3)	C11—C12—C13—O4	1.7 (3)
O3—N1—C4—C3	−5.2 (3)	C17—C12—C13—C14	−0.9 (3)
O2—N1—C4—C3	174.75 (18)	C11—C12—C13—C14	−179.17 (17)
C3—C4—C5—C6	0.2 (3)	O4—C13—C14—C15	−179.76 (19)
N1—C4—C5—C6	−179.88 (17)	C12—C13—C14—C15	1.1 (3)
C4—C5—C6—C7	177.95 (18)	C13—C14—C15—C16	−0.4 (3)
C4—C5—C6—C1	−1.0 (3)	C14—C15—C16—C17	−0.6 (3)
O1—C1—C6—C5	179.14 (18)	C14—C15—C16—N4	178.00 (18)
C2—C1—C6—C5	0.8 (3)	O5—N4—C16—C17	−4.5 (3)
O1—C1—C6—C7	0.2 (3)	O6—N4—C16—C17	175.25 (19)
C2—C1—C6—C7	−178.14 (17)	O5—N4—C16—C15	176.89 (18)
C8—N2—C7—C6	179.92 (17)	O6—N4—C16—C15	−3.4 (3)
C5—C6—C7—N2	−179.22 (18)	C15—C16—C17—C12	0.8 (3)
C1—C6—C7—N2	−0.2 (3)	N4—C16—C17—C12	−177.83 (17)
C7—N2—C8—C9	−128.3 (2)	C11—C12—C17—C16	178.29 (17)
N2—C8—C9—C10	69.6 (2)	C13—C12—C17—C16	0.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H3N···O1	0.93 (3)	1.77 (3)	2.583 (2)	145 (3)
N3—H2N···O4	0.90 (3)	1.93 (3)	2.642 (2)	135 (2)
N3—H2N···O4ⁱ	0.90 (3)	2.17 (3)	2.891 (2)	136 (2)

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆N₄O₆
M_r	372.34
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	200
a, b, c (Å)	11.5698 (5), 13.0393 (6), 22.0393 (10)
V (Å³)	3324.9 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.31 × 0.17 × 0.15

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.890, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	23432, 4120, 2286
R_int	0.084
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.138, 1.03
No. of reflections	4120
No. of parameters	252
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.30

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H3N···O1	0.93 (3)	1.77 (3)	2.583 (2)	145 (3)
N3—H2N···O4	0.90 (3)	1.93 (3)	2.642 (2)	135 (2)
N3—H2N···O4ⁱ	0.90 (3)	2.17 (3)	2.891 (2)	136 (2)

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

This work was supported by the Priority Research Centers Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (2011–0030747).

References

Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Ha, K. (2012). Acta Cryst. E68, o1221. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar