organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

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[Gao, M. Z., Gao, J., Xu, Z. L. & Zingaro, R. A. (2002). Tetrahedron Lett. 43, 5001-5003.]); Redlich & Hossain (2004[Redlich, M. & Hossain, M. M. (2004). Tetrahedron Lett. 45, 8987-8990.]). For related structures, see: Wang et al. (2004[Wang, R. H., Han, L., Sun, Y. Q., Gong, Y. Q., Yuan, D. Q. & Hong, M. C. (2004). J. Mol. Struct. 694, 79-83.]); Huang & Yang (2008[Huang, W.-W. & Yang, S.-P. (2008). Acta Cryst. E64, m525-m526.]).

[Scheme 1]

Experimental

Crystal data
  • C26H18N4O6

  • Mr = 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[Rigaku/MSC (2004). CrystalClear and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]) Tmin = 0.977, Tmax = 0.981

  • 11020 measured reflections

  • 4108 independent reflections

  • 3412 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Rigaku/MSC (2004). CrystalClear and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004[Rigaku/MSC (2004). CrystalClear and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]).

Supporting information


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.

Refinement top

H atoms bonded to C were placed in calculated positions with C—H = 0.95 Å and refined as riding model with Uiso(H) = 1.2Ueq(C). H atoms bonded to N were refined isotropically.

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
[Figure 1] 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
C26H18N4O6F(000) = 1000
Mr = 482.44Dx = 1.436 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71070 Å
a = 12.568 (3) ÅCell parameters from 5737 reflections
b = 12.003 (3) Åθ = 1.7–27.9°
c = 14.858 (4) ŵ = 0.11 mm1
β = 95.324 (2)°T = 113 K
V = 2231.8 (11) Å3Prism, colorless
Z = 40.22 × 0.20 × 0.18 mm
Data collection top
Rigaku Saturn
diffractometer
4108 independent reflections
Radiation source: Rotating anode3412 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.034
Detector resolution: 7.31 pixels mm-1θmax = 25.5°, θmin = 2.0°
ω scansh = 1511
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2004)
k = 1314
Tmin = 0.977, Tmax = 0.981l = 1217
11020 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0639P)2]
where P = (Fo2 + 2Fc2)/3
4108 reflections(Δ/σ)max < 0.001
334 parametersΔρmax = 0.20 e Å3
2 restraintsΔρmin = 0.27 e Å3
Crystal data top
C26H18N4O6V = 2231.8 (11) Å3
Mr = 482.44Z = 4
Monoclinic, P21/nMo Kα radiation
a = 12.568 (3) ŵ = 0.11 mm1
b = 12.003 (3) ÅT = 113 K
c = 14.858 (4) Å0.22 × 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)
Tmin = 0.977, Tmax = 0.981Rint = 0.034
11020 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0382 restraints
wR(F2) = 0.098H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.20 e Å3
4108 reflectionsΔρmin = 0.27 e Å3
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
xyzUiso*/Ueq
N10.22874 (9)0.61297 (10)0.24831 (8)0.0245 (3)
N20.17963 (9)0.37120 (10)0.06868 (8)0.0191 (3)
N30.39547 (9)0.03271 (10)0.15619 (8)0.0209 (3)
N40.45085 (10)0.31187 (10)0.09135 (8)0.0268 (3)
O10.19449 (8)0.70898 (9)0.25307 (8)0.0328 (3)
O20.26451 (9)0.56407 (9)0.31202 (7)0.0331 (3)
O30.30986 (7)0.23718 (8)0.07673 (6)0.0258 (2)
O40.44656 (8)0.04883 (8)0.29288 (7)0.0261 (2)
O50.48585 (9)0.40159 (9)0.06211 (8)0.0390 (3)
O60.42693 (9)0.29307 (9)0.17211 (7)0.0350 (3)
C10.22503 (10)0.55285 (11)0.16268 (9)0.0197 (3)
C20.17265 (11)0.60088 (12)0.09468 (10)0.0242 (3)
H20.14440.67410.10130.029*
C30.16220 (11)0.54058 (12)0.01700 (10)0.0228 (3)
H30.12610.57240.03020.027*
C40.20437 (10)0.43306 (11)0.00715 (9)0.0176 (3)
C50.26065 (10)0.38784 (11)0.07520 (9)0.0187 (3)
H50.29230.31620.06770.022*
C60.27002 (10)0.44780 (11)0.15348 (10)0.0202 (3)
H60.30710.41710.20060.024*
C70.22510 (10)0.27388 (11)0.10011 (9)0.0192 (3)
C80.16061 (11)0.20871 (11)0.16179 (9)0.0196 (3)
C90.05533 (11)0.18147 (12)0.13161 (10)0.0228 (3)
H90.02320.21300.07710.027*
C100.00279 (11)0.10879 (12)0.18054 (10)0.0250 (3)
H100.07460.09100.15980.030*
C110.04420 (11)0.06229 (12)0.25960 (10)0.0257 (3)
H110.00550.01050.29230.031*
C120.14757 (11)0.09124 (12)0.29113 (10)0.0228 (3)
H120.17850.06020.34630.027*
C130.20747 (11)0.16517 (11)0.24363 (9)0.0198 (3)
C140.31259 (10)0.20675 (12)0.28613 (9)0.0199 (3)
C150.31442 (12)0.31004 (12)0.32959 (10)0.0270 (3)
H150.25110.35360.32660.032*
C160.40666 (13)0.35024 (14)0.37692 (10)0.0308 (4)
H160.40610.42060.40620.037*
C170.49948 (12)0.28782 (13)0.38149 (10)0.0287 (4)
H170.56310.31530.41340.034*
C180.49917 (11)0.18540 (13)0.33941 (9)0.0255 (3)
H180.56270.14220.34300.031*
C190.40649 (11)0.14455 (11)0.29155 (9)0.0199 (3)
C200.41647 (10)0.03335 (12)0.24765 (9)0.0203 (3)
C210.40998 (10)0.05654 (11)0.09698 (9)0.0195 (3)
C220.46411 (10)0.15411 (12)0.12407 (10)0.0226 (3)
H220.49220.16330.18520.027*
C230.47664 (11)0.23714 (12)0.06188 (10)0.0235 (3)
H230.51320.30390.07990.028*
C240.43563 (11)0.22264 (12)0.02687 (9)0.0224 (3)
C250.38144 (11)0.12659 (12)0.05546 (10)0.0247 (3)
H250.35380.11810.11680.030*
C260.36826 (11)0.04339 (12)0.00675 (9)0.0226 (3)
H260.33090.02280.01160.027*
H2A0.1284 (10)0.3995 (13)0.1007 (10)0.030 (4)*
H3A0.3673 (12)0.0956 (10)0.1315 (10)0.032 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0246 (6)0.0244 (7)0.0242 (7)0.0037 (5)0.0001 (5)0.0051 (5)
N20.0198 (6)0.0199 (6)0.0181 (6)0.0026 (5)0.0044 (5)0.0019 (5)
N30.0223 (6)0.0222 (6)0.0185 (6)0.0058 (5)0.0036 (5)0.0046 (5)
N40.0285 (7)0.0276 (7)0.0246 (7)0.0078 (6)0.0045 (5)0.0019 (6)
O10.0371 (6)0.0241 (6)0.0371 (6)0.0037 (5)0.0034 (5)0.0123 (5)
O20.0468 (7)0.0330 (6)0.0202 (6)0.0023 (5)0.0059 (5)0.0015 (5)
O30.0225 (5)0.0294 (6)0.0265 (6)0.0061 (4)0.0077 (4)0.0091 (4)
O40.0310 (6)0.0267 (6)0.0211 (5)0.0076 (5)0.0053 (4)0.0071 (4)
O50.0576 (8)0.0245 (6)0.0347 (7)0.0028 (5)0.0027 (5)0.0042 (5)
O60.0451 (7)0.0392 (7)0.0208 (6)0.0076 (5)0.0039 (5)0.0028 (5)
C10.0194 (7)0.0206 (7)0.0184 (7)0.0036 (6)0.0012 (5)0.0036 (6)
C20.0277 (8)0.0183 (7)0.0261 (8)0.0037 (6)0.0001 (6)0.0027 (6)
C30.0274 (8)0.0204 (7)0.0211 (7)0.0031 (6)0.0046 (6)0.0010 (6)
C40.0156 (7)0.0195 (7)0.0171 (7)0.0023 (5)0.0013 (5)0.0012 (6)
C50.0177 (7)0.0168 (7)0.0216 (7)0.0002 (6)0.0020 (5)0.0013 (6)
C60.0180 (7)0.0210 (7)0.0220 (7)0.0021 (6)0.0038 (5)0.0006 (6)
C70.0178 (7)0.0217 (7)0.0179 (7)0.0000 (6)0.0002 (5)0.0007 (6)
C80.0203 (7)0.0184 (7)0.0205 (7)0.0034 (6)0.0044 (6)0.0018 (6)
C90.0228 (8)0.0233 (8)0.0223 (7)0.0030 (6)0.0024 (6)0.0011 (6)
C100.0206 (7)0.0240 (8)0.0309 (8)0.0008 (6)0.0046 (6)0.0001 (6)
C110.0266 (8)0.0208 (7)0.0313 (8)0.0004 (6)0.0113 (6)0.0035 (6)
C120.0251 (8)0.0216 (7)0.0225 (7)0.0045 (6)0.0060 (6)0.0042 (6)
C130.0204 (7)0.0192 (7)0.0203 (7)0.0049 (6)0.0055 (5)0.0011 (6)
C140.0221 (8)0.0224 (7)0.0158 (7)0.0005 (6)0.0048 (5)0.0049 (6)
C150.0274 (8)0.0248 (8)0.0298 (8)0.0026 (6)0.0071 (6)0.0000 (7)
C160.0397 (9)0.0268 (8)0.0268 (8)0.0067 (7)0.0070 (7)0.0044 (7)
C170.0295 (8)0.0364 (9)0.0195 (8)0.0081 (7)0.0003 (6)0.0011 (7)
C180.0214 (8)0.0341 (8)0.0206 (8)0.0010 (6)0.0009 (6)0.0060 (6)
C190.0215 (7)0.0224 (7)0.0164 (7)0.0006 (6)0.0051 (5)0.0054 (6)
C200.0155 (7)0.0262 (8)0.0196 (7)0.0018 (6)0.0043 (5)0.0042 (6)
C210.0170 (7)0.0231 (7)0.0192 (7)0.0016 (6)0.0052 (5)0.0024 (6)
C220.0207 (7)0.0264 (8)0.0207 (7)0.0043 (6)0.0019 (6)0.0034 (6)
C230.0216 (7)0.0257 (8)0.0239 (8)0.0033 (6)0.0048 (6)0.0033 (6)
C240.0209 (7)0.0240 (7)0.0229 (8)0.0043 (6)0.0062 (6)0.0008 (6)
C250.0258 (8)0.0300 (8)0.0182 (7)0.0046 (7)0.0009 (6)0.0041 (6)
C260.0229 (7)0.0232 (7)0.0218 (8)0.0013 (6)0.0019 (6)0.0062 (6)
Geometric parameters (Å, º) top
N1—O11.2299 (16)C10—C111.383 (2)
N1—O21.2337 (16)C10—H100.9500
N1—C11.4672 (18)C11—C121.384 (2)
N2—C71.3636 (18)C11—H110.9500
N2—C41.4080 (17)C12—C131.3966 (19)
N2—H2A0.902 (9)C12—H120.9500
N3—C201.3601 (18)C13—C141.4962 (19)
N3—C211.4088 (18)C14—C191.3925 (19)
N3—H3A0.898 (9)C14—C151.397 (2)
N4—O51.2273 (17)C15—C161.386 (2)
N4—O61.2306 (16)C15—H150.9500
N4—C241.4613 (19)C16—C171.383 (2)
O3—C71.2322 (16)C16—H160.9500
O4—C201.2330 (17)C17—C181.379 (2)
C1—C21.3821 (19)C17—H170.9500
C1—C61.3835 (19)C18—C191.396 (2)
C2—C31.379 (2)C18—H180.9500
C2—H20.9500C19—C201.496 (2)
C3—C41.3977 (19)C21—C221.3948 (19)
C3—H30.9500C21—C261.402 (2)
C4—C51.3964 (18)C22—C231.378 (2)
C5—C61.3820 (19)C22—H220.9500
C5—H50.9500C23—C241.382 (2)
C6—H60.9500C23—H230.9500
C7—C81.4988 (18)C24—C251.386 (2)
C8—C91.396 (2)C25—C261.381 (2)
C8—C131.4021 (19)C25—H250.9500
C9—C101.3862 (19)C26—H260.9500
C9—H90.9500
O1—N1—O2123.52 (12)C11—C12—C13121.44 (14)
O1—N1—C1118.14 (12)C11—C12—H12119.3
O2—N1—C1118.33 (12)C13—C12—H12119.3
C7—N2—C4127.52 (11)C12—C13—C8118.19 (13)
C7—N2—H2A116.1 (10)C12—C13—C14119.67 (12)
C4—N2—H2A116.4 (10)C8—C13—C14121.67 (12)
C20—N3—C21127.15 (12)C19—C14—C15118.14 (13)
C20—N3—H3A115.9 (11)C19—C14—C13123.78 (13)
C21—N3—H3A116.9 (11)C15—C14—C13117.85 (12)
O5—N4—O6123.58 (13)C16—C15—C14121.38 (14)
O5—N4—C24118.39 (12)C16—C15—H15119.3
O6—N4—C24118.03 (13)C14—C15—H15119.3
C2—C1—C6121.73 (13)C17—C16—C15119.90 (15)
C2—C1—N1118.98 (12)C17—C16—H16120.0
C6—C1—N1119.24 (12)C15—C16—H16120.0
C3—C2—C1118.81 (13)C18—C17—C16119.60 (14)
C3—C2—H2120.6C18—C17—H17120.2
C1—C2—H2120.6C16—C17—H17120.2
C2—C3—C4120.51 (13)C17—C18—C19120.74 (14)
C2—C3—H3119.7C17—C18—H18119.6
C4—C3—H3119.7C19—C18—H18119.6
C5—C4—C3119.71 (12)C14—C19—C18120.24 (13)
C5—C4—N2122.60 (12)C14—C19—C20123.93 (13)
C3—C4—N2117.45 (12)C18—C19—C20115.83 (12)
C6—C5—C4119.70 (13)O4—C20—N3124.15 (13)
C6—C5—H5120.1O4—C20—C19120.66 (12)
C4—C5—H5120.1N3—C20—C19115.11 (12)
C5—C6—C1119.46 (13)C22—C21—C26119.97 (13)
C5—C6—H6120.3C22—C21—N3123.10 (13)
C1—C6—H6120.3C26—C21—N3116.93 (12)
O3—C7—N2123.74 (12)C23—C22—C21119.78 (13)
O3—C7—C8121.10 (12)C23—C22—H22120.1
N2—C7—C8115.04 (11)C21—C22—H22120.1
C9—C8—C13120.04 (12)C22—C23—C24119.55 (13)
C9—C8—C7118.43 (12)C22—C23—H23120.2
C13—C8—C7121.16 (12)C24—C23—H23120.2
C10—C9—C8120.59 (14)C23—C24—C25121.78 (14)
C10—C9—H9119.7C23—C24—N4118.26 (13)
C8—C9—H9119.7C25—C24—N4119.95 (13)
C11—C10—C9119.69 (13)C26—C25—C24118.85 (13)
C11—C10—H10120.2C26—C25—H25120.6
C9—C10—H10120.2C24—C25—H25120.6
C10—C11—C12119.98 (13)C25—C26—C21120.06 (13)
C10—C11—H11120.0C25—C26—H26120.0
C12—C11—H11120.0C21—C26—H26120.0
O1—N1—C1—C27.31 (19)C12—C13—C14—C1596.39 (16)
O2—N1—C1—C2171.63 (12)C8—C13—C14—C1575.56 (17)
O1—N1—C1—C6175.39 (12)C19—C14—C15—C160.0 (2)
O2—N1—C1—C65.67 (18)C13—C14—C15—C16174.64 (13)
C6—C1—C2—C32.2 (2)C14—C15—C16—C170.2 (2)
N1—C1—C2—C3175.07 (12)C15—C16—C17—C180.5 (2)
C1—C2—C3—C40.3 (2)C16—C17—C18—C190.6 (2)
C2—C3—C4—C52.2 (2)C15—C14—C19—C180.05 (19)
C2—C3—C4—N2172.40 (13)C13—C14—C19—C18174.22 (12)
C7—N2—C4—C517.4 (2)C15—C14—C19—C20179.36 (12)
C7—N2—C4—C3168.16 (13)C13—C14—C19—C206.4 (2)
C3—C4—C5—C62.92 (19)C17—C18—C19—C140.4 (2)
N2—C4—C5—C6171.38 (12)C17—C18—C19—C20179.09 (12)
C4—C5—C6—C11.14 (19)C21—N3—C20—O44.3 (2)
C2—C1—C6—C51.4 (2)C21—N3—C20—C19172.44 (12)
N1—C1—C6—C5175.80 (12)C14—C19—C20—O4123.24 (15)
C4—N2—C7—O315.2 (2)C18—C19—C20—O457.33 (17)
C4—N2—C7—C8160.85 (12)C14—C19—C20—N359.93 (17)
O3—C7—C8—C9121.93 (15)C18—C19—C20—N3119.51 (13)
N2—C7—C8—C954.26 (17)C20—N3—C21—C229.9 (2)
O3—C7—C8—C1351.05 (19)C20—N3—C21—C26170.91 (12)
N2—C7—C8—C13132.75 (13)C26—C21—C22—C230.2 (2)
C13—C8—C9—C101.9 (2)N3—C21—C22—C23178.94 (12)
C7—C8—C9—C10171.13 (13)C21—C22—C23—C240.2 (2)
C8—C9—C10—C110.4 (2)C22—C23—C24—C250.3 (2)
C9—C10—C11—C122.2 (2)C22—C23—C24—N4179.58 (12)
C10—C11—C12—C131.5 (2)O5—N4—C24—C239.98 (19)
C11—C12—C13—C80.9 (2)O6—N4—C24—C23170.63 (12)
C11—C12—C13—C14171.37 (12)O5—N4—C24—C25170.15 (13)
C9—C8—C13—C122.56 (19)O6—N4—C24—C259.23 (19)
C7—C8—C13—C12170.31 (12)C23—C24—C25—C260.0 (2)
C9—C8—C13—C14169.51 (12)N4—C24—C25—C26179.89 (12)
C7—C8—C13—C1417.62 (19)C24—C25—C26—C210.4 (2)
C12—C13—C14—C1977.90 (17)C22—C21—C26—C250.5 (2)
C8—C13—C14—C19110.15 (15)N3—C21—C26—C25178.68 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O4i0.90 (1)2.01 (1)2.8763 (17)160 (1)
N3—H3A···O30.90 (1)1.99 (1)2.8878 (17)178 (1)
C5—H5···O30.952.342.9137 (18)119
C6—H6···O1ii0.952.593.2340 (19)125
C22—H22···O40.952.222.8353 (19)121
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x+1/2, y1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC26H18N4O6
Mr482.44
Crystal system, space groupMonoclinic, P21/n
Temperature (K)113
a, b, c (Å)12.568 (3), 12.003 (3), 14.858 (4)
β (°) 95.324 (2)
V3)2231.8 (11)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.22 × 0.20 × 0.18
Data collection
DiffractometerRigaku Saturn
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2004)
Tmin, Tmax0.977, 0.981
No. of measured, independent and
observed [I > 2σ(I)] reflections
11020, 4108, 3412
Rint0.034
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.098, 1.02
No. of reflections4108
No. of parameters334
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N2—H2A···O4i0.902 (14)2.012 (14)2.8763 (17)160.1 (13)
N3—H3A···O30.898 (13)1.991 (13)2.8878 (17)178.0 (14)
C5—H5···O30.952.342.9137 (18)119
C6—H6···O1ii0.952.593.2340 (19)125
C22—H22···O40.952.222.8353 (19)121
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x+1/2, y1/2, z1/2.
 

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

First citationGao, M. Z., Gao, J., Xu, Z. L. & Zingaro, R. A. (2002). Tetrahedron Lett. 43, 5001–5003.  Web of Science CrossRef CAS Google Scholar
First citationHuang, W.-W. & Yang, S.-P. (2008). Acta Cryst. E64, m525–m526.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationRedlich, M. & Hossain, M. M. (2004). Tetrahedron Lett. 45, 8987–8990.  Web of Science CrossRef CAS Google Scholar
First citationRigaku/MSC (2004). CrystalClear and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWang, 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

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