N,N′-Bis(4-nitro­phen­yl)biphenyl-2,2′-dicarboxamide

Wang, G.-Y.; Qin, D.-B.; Guo, L.-H.; Luo, J.-W.

doi:10.1107/S1600536810005283

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o644

doi:10.1107/S1600536810005283

Open

access

N,N′-Bis(4-nitrophenyl)biphenyl-2,2′-dicarboxamide

Gui-Yu Wang,^a Da-Bin Qin,^a ^* Li-Hui Guo ^a and Jie-Wei Luo ^a

^aSchool of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
^*Correspondence e-mail: qindabincwnu@yahoo.com.cn

(Received 12 January 2010; accepted 9 February 2010; online 17 February 2010)

In the title compound, C₂₆H₁₈N₄O₆, the amide units are approximately coplanar with the benzene ring bonded to the N atom [dihedral angles of 10.59 (10) and 24.00 (12)°], but twisted significantly out of the plane of the benzene ring bonded to the carbonyl C atom [dihedral angles of 57.82 (9) and 58.05 (9)°]. The dihedral angle between the two rings of the biphenyl unit is 77.66 (4)°. Intramolecular N—H⋯O hydrogen bonds and weak C—H⋯O interactions occur. The crystal structure is stabilized by intermolecular N—H⋯O hydrogen bonds and C—H⋯O contacts.

Related literature

For the synthesis, see: Gao et al. (2002 ); Redlich & Hossain (2004 ). For related structures, see: Wang et al. (2004 ); Huang & Yang (2008 ).

Experimental

Crystal data

C₂₆H₁₈N₄O₆
M_r = 482.44
Monoclinic, P 2₁ /n
a = 12.568 (3) Å
b = 12.003 (3) Å
c = 14.858 (4) Å
β = 95.324 (2)°
V = 2231.8 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 113 K
0.22 × 0.20 × 0.18 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004 ) T_min = 0.977, T_max = 0.981
11020 measured reflections
4108 independent reflections
3412 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.098
S = 1.02
4108 reflections
334 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O4ⁱ	0.90 (1)	2.01 (1)	2.8763 (17)	160 (1)
N3—H3A⋯O3	0.90 (1)	1.99 (1)	2.8878 (17)	178 (1)
C5—H5⋯O3	0.95	2.34	2.9137 (18)	119
C6—H6⋯O1ⁱⁱ	0.95	2.59	3.2340 (19)	125
C22—H22⋯O4	0.95	2.22	2.8353 (19)	121
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2004); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004).

Supporting information

Crystal structure: contains datablocks shelxl, I. DOI: 10.1107/S1600536810005283/bt5169sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810005283/bt5169Isup2.hkl

checkCIF report

Comment top

In the title compound the amide units are fairly coplanar with the phenyl ring bonded to the N atom [10.59 (10)° and 24.00 (12)°], but significantly twisted out of the plane of the phenyl ring bonded to the carbonyl C atom [57.82 (9)° and 58.05 (9)°]. The dihedral angle between the two rings of the biphenyl unit is 77.66 (4)°. The crystal structure is stabilized by intramolecular and intermolecular N—H···O hydrogen bonds. In addition, there are short intramolecular and intermolecular C—H···O contacts (Table 1).

Related literature top

For the synthesis, see: Gao et al. (2002); Redlich & Hossain (2004). For related structures, see: Wang et al. (2004); Huang & Yang (2008).

Experimental top

The title compound was prepared according to the reported procedure of Gao et al. (2002) and Redlich & Hossain (2004). Colorless single crystals suitable for X-ray diffraction were obtained by recrystallization from acetonitrile.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2004); cell refinement: CrystalClear (Rigaku/MSC, 2004); data reduction: CrystalClear (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004).

Figures top

Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering.

N,N'-Bis(4-nitrophenyl)biphenyl-2,2'-dicarboxamide top

Crystal data top

C₂₆H₁₈N₄O₆	F(000) = 1000
M_r = 482.44	D_x = 1.436 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71070 Å
a = 12.568 (3) Å	Cell parameters from 5737 reflections
b = 12.003 (3) Å	θ = 1.7–27.9°
c = 14.858 (4) Å	µ = 0.11 mm⁻¹
β = 95.324 (2)°	T = 113 K
V = 2231.8 (11) Å³	Prism, colorless
Z = 4	0.22 × 0.20 × 0.18 mm

Data collection top

Rigaku Saturn diffractometer	4108 independent reflections
Radiation source: Rotating anode	3412 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.034
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.5°, θ_min = 2.0°
ω scans	h = −15→11
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004)	k = −13→14
T_min = 0.977, T_max = 0.981	l = −12→17
11020 measured reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0639P)²] where P = (F_o² + 2F_c²)/3
4108 reflections	(Δ/σ)_max < 0.001
334 parameters	Δρ_max = 0.20 e Å⁻³
2 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₆H₁₈N₄O₆	V = 2231.8 (11) Å³
M_r = 482.44	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.568 (3) Å	µ = 0.11 mm⁻¹
b = 12.003 (3) Å	T = 113 K
c = 14.858 (4) Å	0.22 × 0.20 × 0.18 mm
β = 95.324 (2)°

Data collection top

Rigaku Saturn diffractometer	4108 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004)	3412 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.981	R_int = 0.034
11020 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	2 restraints
wR(F²) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.20 e Å⁻³
4108 reflections	Δρ_min = −0.27 e Å⁻³
334 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
N1	0.22874 (9)	0.61297 (10)	−0.24831 (8)	0.0245 (3)
N2	0.17963 (9)	0.37120 (10)	0.06868 (8)	0.0191 (3)
N3	0.39547 (9)	0.03271 (10)	0.15619 (8)	0.0209 (3)
N4	0.45085 (10)	−0.31187 (10)	−0.09135 (8)	0.0268 (3)
O1	0.19449 (8)	0.70898 (9)	−0.25307 (8)	0.0328 (3)
O2	0.26451 (9)	0.56407 (9)	−0.31202 (7)	0.0331 (3)
O3	0.30986 (7)	0.23718 (8)	0.07673 (6)	0.0258 (2)
O4	0.44656 (8)	−0.04883 (8)	0.29288 (7)	0.0261 (2)
O5	0.48585 (9)	−0.40159 (9)	−0.06211 (8)	0.0390 (3)
O6	0.42693 (9)	−0.29307 (9)	−0.17211 (7)	0.0350 (3)
C1	0.22503 (10)	0.55285 (11)	−0.16268 (9)	0.0197 (3)
C2	0.17265 (11)	0.60088 (12)	−0.09468 (10)	0.0242 (3)
H2	0.1444	0.6741	−0.1013	0.029*
C3	0.16220 (11)	0.54058 (12)	−0.01700 (10)	0.0228 (3)
H3	0.1261	0.5724	0.0302	0.027*
C4	0.20437 (10)	0.43306 (11)	−0.00715 (9)	0.0176 (3)
C5	0.26065 (10)	0.38784 (11)	−0.07520 (9)	0.0187 (3)
H5	0.2923	0.3162	−0.0677	0.022*
C6	0.27002 (10)	0.44780 (11)	−0.15348 (10)	0.0202 (3)
H6	0.3071	0.4171	−0.2006	0.024*
C7	0.22510 (10)	0.27388 (11)	0.10011 (9)	0.0192 (3)
C8	0.16061 (11)	0.20871 (11)	0.16179 (9)	0.0196 (3)
C9	0.05533 (11)	0.18147 (12)	0.13161 (10)	0.0228 (3)
H9	0.0232	0.2130	0.0771	0.027*
C10	−0.00279 (11)	0.10879 (12)	0.18054 (10)	0.0250 (3)
H10	−0.0746	0.0910	0.1598	0.030*
C11	0.04420 (11)	0.06229 (12)	0.25960 (10)	0.0257 (3)
H11	0.0055	0.0105	0.2923	0.031*
C12	0.14757 (11)	0.09124 (12)	0.29113 (10)	0.0228 (3)
H12	0.1785	0.0602	0.3463	0.027*
C13	0.20747 (11)	0.16517 (11)	0.24363 (9)	0.0198 (3)
C14	0.31259 (10)	0.20675 (12)	0.28613 (9)	0.0199 (3)
C15	0.31442 (12)	0.31004 (12)	0.32959 (10)	0.0270 (3)
H15	0.2511	0.3536	0.3266	0.032*
C16	0.40666 (13)	0.35024 (14)	0.37692 (10)	0.0308 (4)
H16	0.4061	0.4206	0.4062	0.037*
C17	0.49948 (12)	0.28782 (13)	0.38149 (10)	0.0287 (4)
H17	0.5631	0.3153	0.4134	0.034*
C18	0.49917 (11)	0.18540 (13)	0.33941 (9)	0.0255 (3)
H18	0.5627	0.1422	0.3430	0.031*
C19	0.40649 (11)	0.14455 (11)	0.29155 (9)	0.0199 (3)
C20	0.41647 (10)	0.03335 (12)	0.24765 (9)	0.0203 (3)
C21	0.40998 (10)	−0.05654 (11)	0.09698 (9)	0.0195 (3)
C22	0.46411 (10)	−0.15411 (12)	0.12407 (10)	0.0226 (3)
H22	0.4922	−0.1633	0.1852	0.027*
C23	0.47664 (11)	−0.23714 (12)	0.06188 (10)	0.0235 (3)
H23	0.5132	−0.3039	0.0799	0.028*
C24	0.43563 (11)	−0.22264 (12)	−0.02687 (9)	0.0224 (3)
C25	0.38144 (11)	−0.12659 (12)	−0.05546 (10)	0.0247 (3)
H25	0.3538	−0.1181	−0.1168	0.030*
C26	0.36826 (11)	−0.04339 (12)	0.00675 (9)	0.0226 (3)
H26	0.3309	0.0228	−0.0116	0.027*
H2A	0.1284 (10)	0.3995 (13)	0.1007 (10)	0.030 (4)*
H3A	0.3673 (12)	0.0956 (10)	0.1315 (10)	0.032 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0246 (6)	0.0244 (7)	0.0242 (7)	−0.0037 (5)	0.0001 (5)	0.0051 (5)
N2	0.0198 (6)	0.0199 (6)	0.0181 (6)	0.0026 (5)	0.0044 (5)	0.0019 (5)
N3	0.0223 (6)	0.0222 (6)	0.0185 (6)	0.0058 (5)	0.0036 (5)	0.0046 (5)
N4	0.0285 (7)	0.0276 (7)	0.0246 (7)	−0.0078 (6)	0.0045 (5)	−0.0019 (6)
O1	0.0371 (6)	0.0241 (6)	0.0371 (6)	0.0037 (5)	0.0034 (5)	0.0123 (5)
O2	0.0468 (7)	0.0330 (6)	0.0202 (6)	−0.0023 (5)	0.0059 (5)	0.0015 (5)
O3	0.0225 (5)	0.0294 (6)	0.0265 (6)	0.0061 (4)	0.0077 (4)	0.0091 (4)
O4	0.0310 (6)	0.0267 (6)	0.0211 (5)	0.0076 (5)	0.0053 (4)	0.0071 (4)
O5	0.0576 (8)	0.0245 (6)	0.0347 (7)	0.0028 (5)	0.0027 (5)	−0.0042 (5)
O6	0.0451 (7)	0.0392 (7)	0.0208 (6)	−0.0076 (5)	0.0039 (5)	−0.0028 (5)
C1	0.0194 (7)	0.0206 (7)	0.0184 (7)	−0.0036 (6)	−0.0012 (5)	0.0036 (6)
C2	0.0277 (8)	0.0183 (7)	0.0261 (8)	0.0037 (6)	0.0001 (6)	0.0027 (6)
C3	0.0274 (8)	0.0204 (7)	0.0211 (7)	0.0031 (6)	0.0046 (6)	−0.0010 (6)
C4	0.0156 (7)	0.0195 (7)	0.0171 (7)	−0.0023 (5)	−0.0013 (5)	0.0012 (6)
C5	0.0177 (7)	0.0168 (7)	0.0216 (7)	0.0002 (6)	0.0020 (5)	0.0013 (6)
C6	0.0180 (7)	0.0210 (7)	0.0220 (7)	−0.0021 (6)	0.0038 (5)	−0.0006 (6)
C7	0.0178 (7)	0.0217 (7)	0.0179 (7)	0.0000 (6)	−0.0002 (5)	0.0007 (6)
C8	0.0203 (7)	0.0184 (7)	0.0205 (7)	0.0034 (6)	0.0044 (6)	0.0018 (6)
C9	0.0228 (8)	0.0233 (8)	0.0223 (7)	0.0030 (6)	0.0024 (6)	0.0011 (6)
C10	0.0206 (7)	0.0240 (8)	0.0309 (8)	−0.0008 (6)	0.0046 (6)	−0.0001 (6)
C11	0.0266 (8)	0.0208 (7)	0.0313 (8)	−0.0004 (6)	0.0113 (6)	0.0035 (6)
C12	0.0251 (8)	0.0216 (7)	0.0225 (7)	0.0045 (6)	0.0060 (6)	0.0042 (6)
C13	0.0204 (7)	0.0192 (7)	0.0203 (7)	0.0049 (6)	0.0055 (5)	0.0011 (6)
C14	0.0221 (8)	0.0224 (7)	0.0158 (7)	0.0005 (6)	0.0048 (5)	0.0049 (6)
C15	0.0274 (8)	0.0248 (8)	0.0298 (8)	0.0026 (6)	0.0071 (6)	0.0000 (7)
C16	0.0397 (9)	0.0268 (8)	0.0268 (8)	−0.0067 (7)	0.0070 (7)	−0.0044 (7)
C17	0.0295 (8)	0.0364 (9)	0.0195 (8)	−0.0081 (7)	−0.0003 (6)	0.0011 (7)
C18	0.0214 (8)	0.0341 (8)	0.0206 (8)	0.0010 (6)	0.0009 (6)	0.0060 (6)
C19	0.0215 (7)	0.0224 (7)	0.0164 (7)	0.0006 (6)	0.0051 (5)	0.0054 (6)
C20	0.0155 (7)	0.0262 (8)	0.0196 (7)	0.0018 (6)	0.0043 (5)	0.0042 (6)
C21	0.0170 (7)	0.0231 (7)	0.0192 (7)	−0.0016 (6)	0.0052 (5)	0.0024 (6)
C22	0.0207 (7)	0.0264 (8)	0.0207 (7)	0.0043 (6)	0.0019 (6)	0.0034 (6)
C23	0.0216 (7)	0.0257 (8)	0.0239 (8)	0.0033 (6)	0.0048 (6)	0.0033 (6)
C24	0.0209 (7)	0.0240 (7)	0.0229 (8)	−0.0043 (6)	0.0062 (6)	−0.0008 (6)
C25	0.0258 (8)	0.0300 (8)	0.0182 (7)	−0.0046 (7)	0.0009 (6)	0.0041 (6)
C26	0.0229 (7)	0.0232 (7)	0.0218 (8)	0.0013 (6)	0.0019 (6)	0.0062 (6)

Geometric parameters (Å, º) top

N1—O1	1.2299 (16)	C10—C11	1.383 (2)
N1—O2	1.2337 (16)	C10—H10	0.9500
N1—C1	1.4672 (18)	C11—C12	1.384 (2)
N2—C7	1.3636 (18)	C11—H11	0.9500
N2—C4	1.4080 (17)	C12—C13	1.3966 (19)
N2—H2A	0.902 (9)	C12—H12	0.9500
N3—C20	1.3601 (18)	C13—C14	1.4962 (19)
N3—C21	1.4088 (18)	C14—C19	1.3925 (19)
N3—H3A	0.898 (9)	C14—C15	1.397 (2)
N4—O5	1.2273 (17)	C15—C16	1.386 (2)
N4—O6	1.2306 (16)	C15—H15	0.9500
N4—C24	1.4613 (19)	C16—C17	1.383 (2)
O3—C7	1.2322 (16)	C16—H16	0.9500
O4—C20	1.2330 (17)	C17—C18	1.379 (2)
C1—C2	1.3821 (19)	C17—H17	0.9500
C1—C6	1.3835 (19)	C18—C19	1.396 (2)
C2—C3	1.379 (2)	C18—H18	0.9500
C2—H2	0.9500	C19—C20	1.496 (2)
C3—C4	1.3977 (19)	C21—C22	1.3948 (19)
C3—H3	0.9500	C21—C26	1.402 (2)
C4—C5	1.3964 (18)	C22—C23	1.378 (2)
C5—C6	1.3820 (19)	C22—H22	0.9500
C5—H5	0.9500	C23—C24	1.382 (2)
C6—H6	0.9500	C23—H23	0.9500
C7—C8	1.4988 (18)	C24—C25	1.386 (2)
C8—C9	1.396 (2)	C25—C26	1.381 (2)
C8—C13	1.4021 (19)	C25—H25	0.9500
C9—C10	1.3862 (19)	C26—H26	0.9500
C9—H9	0.9500

O1—N1—O2	123.52 (12)	C11—C12—C13	121.44 (14)
O1—N1—C1	118.14 (12)	C11—C12—H12	119.3
O2—N1—C1	118.33 (12)	C13—C12—H12	119.3
C7—N2—C4	127.52 (11)	C12—C13—C8	118.19 (13)
C7—N2—H2A	116.1 (10)	C12—C13—C14	119.67 (12)
C4—N2—H2A	116.4 (10)	C8—C13—C14	121.67 (12)
C20—N3—C21	127.15 (12)	C19—C14—C15	118.14 (13)
C20—N3—H3A	115.9 (11)	C19—C14—C13	123.78 (13)
C21—N3—H3A	116.9 (11)	C15—C14—C13	117.85 (12)
O5—N4—O6	123.58 (13)	C16—C15—C14	121.38 (14)
O5—N4—C24	118.39 (12)	C16—C15—H15	119.3
O6—N4—C24	118.03 (13)	C14—C15—H15	119.3
C2—C1—C6	121.73 (13)	C17—C16—C15	119.90 (15)
C2—C1—N1	118.98 (12)	C17—C16—H16	120.0
C6—C1—N1	119.24 (12)	C15—C16—H16	120.0
C3—C2—C1	118.81 (13)	C18—C17—C16	119.60 (14)
C3—C2—H2	120.6	C18—C17—H17	120.2
C1—C2—H2	120.6	C16—C17—H17	120.2
C2—C3—C4	120.51 (13)	C17—C18—C19	120.74 (14)
C2—C3—H3	119.7	C17—C18—H18	119.6
C4—C3—H3	119.7	C19—C18—H18	119.6
C5—C4—C3	119.71 (12)	C14—C19—C18	120.24 (13)
C5—C4—N2	122.60 (12)	C14—C19—C20	123.93 (13)
C3—C4—N2	117.45 (12)	C18—C19—C20	115.83 (12)
C6—C5—C4	119.70 (13)	O4—C20—N3	124.15 (13)
C6—C5—H5	120.1	O4—C20—C19	120.66 (12)
C4—C5—H5	120.1	N3—C20—C19	115.11 (12)
C5—C6—C1	119.46 (13)	C22—C21—C26	119.97 (13)
C5—C6—H6	120.3	C22—C21—N3	123.10 (13)
C1—C6—H6	120.3	C26—C21—N3	116.93 (12)
O3—C7—N2	123.74 (12)	C23—C22—C21	119.78 (13)
O3—C7—C8	121.10 (12)	C23—C22—H22	120.1
N2—C7—C8	115.04 (11)	C21—C22—H22	120.1
C9—C8—C13	120.04 (12)	C22—C23—C24	119.55 (13)
C9—C8—C7	118.43 (12)	C22—C23—H23	120.2
C13—C8—C7	121.16 (12)	C24—C23—H23	120.2
C10—C9—C8	120.59 (14)	C23—C24—C25	121.78 (14)
C10—C9—H9	119.7	C23—C24—N4	118.26 (13)
C8—C9—H9	119.7	C25—C24—N4	119.95 (13)
C11—C10—C9	119.69 (13)	C26—C25—C24	118.85 (13)
C11—C10—H10	120.2	C26—C25—H25	120.6
C9—C10—H10	120.2	C24—C25—H25	120.6
C10—C11—C12	119.98 (13)	C25—C26—C21	120.06 (13)
C10—C11—H11	120.0	C25—C26—H26	120.0
C12—C11—H11	120.0	C21—C26—H26	120.0

O1—N1—C1—C2	7.31 (19)	C12—C13—C14—C15	−96.39 (16)
O2—N1—C1—C2	−171.63 (12)	C8—C13—C14—C15	75.56 (17)
O1—N1—C1—C6	−175.39 (12)	C19—C14—C15—C16	0.0 (2)
O2—N1—C1—C6	5.67 (18)	C13—C14—C15—C16	174.64 (13)
C6—C1—C2—C3	−2.2 (2)	C14—C15—C16—C17	0.2 (2)
N1—C1—C2—C3	175.07 (12)	C15—C16—C17—C18	−0.5 (2)
C1—C2—C3—C4	0.3 (2)	C16—C17—C18—C19	0.6 (2)
C2—C3—C4—C5	2.2 (2)	C15—C14—C19—C18	0.05 (19)
C2—C3—C4—N2	−172.40 (13)	C13—C14—C19—C18	−174.22 (12)
C7—N2—C4—C5	17.4 (2)	C15—C14—C19—C20	−179.36 (12)
C7—N2—C4—C3	−168.16 (13)	C13—C14—C19—C20	6.4 (2)
C3—C4—C5—C6	−2.92 (19)	C17—C18—C19—C14	−0.4 (2)
N2—C4—C5—C6	171.38 (12)	C17—C18—C19—C20	179.09 (12)
C4—C5—C6—C1	1.14 (19)	C21—N3—C20—O4	−4.3 (2)
C2—C1—C6—C5	1.4 (2)	C21—N3—C20—C19	172.44 (12)
N1—C1—C6—C5	−175.80 (12)	C14—C19—C20—O4	−123.24 (15)
C4—N2—C7—O3	15.2 (2)	C18—C19—C20—O4	57.33 (17)
C4—N2—C7—C8	−160.85 (12)	C14—C19—C20—N3	59.93 (17)
O3—C7—C8—C9	−121.93 (15)	C18—C19—C20—N3	−119.51 (13)
N2—C7—C8—C9	54.26 (17)	C20—N3—C21—C22	−9.9 (2)
O3—C7—C8—C13	51.05 (19)	C20—N3—C21—C26	170.91 (12)
N2—C7—C8—C13	−132.75 (13)	C26—C21—C22—C23	0.2 (2)
C13—C8—C9—C10	−1.9 (2)	N3—C21—C22—C23	−178.94 (12)
C7—C8—C9—C10	171.13 (13)	C21—C22—C23—C24	0.2 (2)
C8—C9—C10—C11	−0.4 (2)	C22—C23—C24—C25	−0.3 (2)
C9—C10—C11—C12	2.2 (2)	C22—C23—C24—N4	179.58 (12)
C10—C11—C12—C13	−1.5 (2)	O5—N4—C24—C23	9.98 (19)
C11—C12—C13—C8	−0.9 (2)	O6—N4—C24—C23	−170.63 (12)
C11—C12—C13—C14	171.37 (12)	O5—N4—C24—C25	−170.15 (13)
C9—C8—C13—C12	2.56 (19)	O6—N4—C24—C25	9.23 (19)
C7—C8—C13—C12	−170.31 (12)	C23—C24—C25—C26	0.0 (2)
C9—C8—C13—C14	−169.51 (12)	N4—C24—C25—C26	−179.89 (12)
C7—C8—C13—C14	17.62 (19)	C24—C25—C26—C21	0.4 (2)
C12—C13—C14—C19	77.90 (17)	C22—C21—C26—C25	−0.5 (2)
C8—C13—C14—C19	−110.15 (15)	N3—C21—C26—C25	178.68 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O4ⁱ	0.90 (1)	2.01 (1)	2.8763 (17)	160 (1)
N3—H3A···O3	0.90 (1)	1.99 (1)	2.8878 (17)	178 (1)
C5—H5···O3	0.95	2.34	2.9137 (18)	119
C6—H6···O1ⁱⁱ	0.95	2.59	3.2340 (19)	125
C22—H22···O4	0.95	2.22	2.8353 (19)	121

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

Experimental details

Crystal data
Chemical formula	C₂₆H₁₈N₄O₆
M_r	482.44
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	113
a, b, c (Å)	12.568 (3), 12.003 (3), 14.858 (4)
β (°)	95.324 (2)
V (Å³)	2231.8 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.22 × 0.20 × 0.18

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2004)
T_min, T_max	0.977, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	11020, 4108, 3412
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.098, 1.02
No. of reflections	4108
No. of parameters	334
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.27

Computer programs: CrystalClear (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Sheldrick, 2008), CrystalStructure (Rigaku/MSC, 2004).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O4ⁱ	0.902 (14)	2.012 (14)	2.8763 (17)	160.1 (13)
N3—H3A···O3	0.898 (13)	1.991 (13)	2.8878 (17)	178.0 (14)
C5—H5···O3	0.95	2.34	2.9137 (18)	119
C6—H6···O1ⁱⁱ	0.95	2.59	3.2340 (19)	125
C22—H22···O4	0.95	2.22	2.8353 (19)	121

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

Acknowledgements

The authors thank the Scientific Researching Fund Projects of China West Normal University (grant No. 06B003) and the Youth Fund Projects of Sichuan Educational Department (grant No. 2006B039).

References

Gao, M. Z., Gao, J., Xu, Z. L. & Zingaro, R. A. (2002). Tetrahedron Lett. 43, 5001–5003. Web of Science CrossRef CAS Google Scholar
Huang, W.-W. & Yang, S.-P. (2008). Acta Cryst. E64, m525–m526. Web of Science CSD CrossRef IUCr Journals Google Scholar
Redlich, M. & Hossain, M. M. (2004). Tetrahedron Lett. 45, 8987–8990. Web of Science CrossRef CAS Google Scholar
Rigaku/MSC (2004). CrystalClear and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, R. H., Han, L., Sun, Y. Q., Gong, Y. Q., Yuan, D. Q. & Hong, M. C. (2004). J. Mol. Struct. 694, 79–83. Web of Science CSD CrossRef CAS Google Scholar