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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): o1360.
Published online 2010 May 15. doi:  10.1107/S1600536810017198
PMCID: PMC2979573

(E)-5-[(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino­meth­yl]-2-methoxy­phenyl 4-bromo­benzene­sulfonate

Abstract

In the title compound, C25H22BrN3O5S, the central benzene ring makes dihedral angles of 32.02 (14), 37.49 (18) and 80.52 (13)°, respectively, with the pyrazolone ring, the bromo­benzene ring and the terminal phenyl ring. This conformation features a short intramolecular C—H(...)O contact that generates an S(6) ring. In the crystal, inversion dimers linked by pairs of C—H(...)O=C hydrogen bonds occur.

Related literature

For general background to Schiff bases, see: Santos et al. (2001 [triangle]). For related structures, see: Chen & Yu (2006 [triangle]); Zhang et al. (2006 [triangle]). For reference structural data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1360-scheme1.jpg

Experimental

Crystal data

  • C25H22BrN3O5S
  • M r = 556.43
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1360-efi1.jpg
  • a = 11.102 (2) Å
  • b = 10.336 (2) Å
  • c = 22.160 (4) Å
  • β = 98.81 (3)°
  • V = 2512.9 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.76 mm−1
  • T = 294 K
  • 0.24 × 0.20 × 0.12 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.628, T max = 0.810
  • 12656 measured reflections
  • 4431 independent reflections
  • 2007 reflections with I > 2σ(I)
  • R int = 0.080

Refinement

  • R[F 2 > 2σ(F 2)] = 0.057
  • wR(F 2) = 0.163
  • S = 1.00
  • 4431 reflections
  • 320 parameters
  • H-atom parameters constrained
  • Δρmax = 0.98 e Å−3
  • Δρmin = −0.82 e Å−3

Data collection: SMART (Bruker, 1999 [triangle]); cell refinement: SAINT (Bruker, 1999 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810017198/hb5442sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017198/hb5442Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

There has been steady growth of interest in the synthesis, structure, and reactivity of Schiff bases due to their potentially biological activities such as protein and enzyme mimics (Santos et al., 2001). Among the large number of compounds, 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one forms a variety of Schiff bases with aldehydes, and the synthesis and crystal structures of some of them, such as (E)-5-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro- 1H-pyrazol-4-yliminomethyl)-2-methoxyphenyl benzenesulfonate (Chen & Yu, 2006) and (E)-4-(2-(4-Chlorobenzyloxy)benzylideneamino) -2,3-dimethyl-1-phenyl-1,2-dihydropyrazol-5-one (Zhang et al., 2006) have been reported.

Structural information is useful when investigating the coordination properties of Schiff bases functioning as ligands. We report here the synthesis and molecular structure of the title Schiff base compound, (I), (Fig. 1)

In the title molecule (Fig. 1), bond lengths and angles are within normal ranges (Allen et al., 1987). The pyrazolone ring (C15—C17/N1—N3/O5) is almost planar, with an r.m.s. deviation for fitted atoms of 0.0331 Å. It makes a dihedral angle of 51.63 (17)° with the attached phenyl ring (C20—C25). The central benzene ring (C7—C12/C14/O3/O4) is nearly planar, with an r.m.s. deviation for fitted atoms of 0.0371 Å. This group makes dihedral angles of 32.02 (14)°, 37.49 (18)° and 80.52 (13)°, respectively, with the the pyrazolone ring (C15—C17/N1—N3/O5), the bromobenzene ring (C1—C6) and the terminal phenyl ring (C20—C25).

An intramolecular C14—H14···O5═C16 hydrogen bond is found in (I) (Table 1), which helps to stabilize the conformation of the molecule. Packing is stabilised by weak, non-classical intermolecular C9—H9···O5═C16 hydrogen bonds that form inversion related dimers (Table 1, Fig. 2).

Experimental

An anhydrous ethanol solution (50 ml) of 5-formyl-2-methoxyphenyl 4-bromobenzenesulfonate (3.71 g, 10 mmol) was added to an anhydrous ethanol solution (50 ml) of 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one (2.03 g, 10 mmol) and the mixture stirred at 350 K for 3 h under N2, giving a yellow precipitate. The product was isolated, recrystallized from acetonitrile, and then dried in a vacuum to give pure compound (I) in 83% yield. Yellow blocks of (I) were obtained by slow evaporation of an acetonitrile solution.

Refinement

The H atoms were included in calculated positions and refined using a riding model approximation. Constrained C—H bond lengths and isotropic U parameters: 0.93 Å and Uiso(H) = 1.2Ueq(C) for Csp2—H; 0.96 Å and Uiso(H) = 1.5Ueq(C) for methyl C—H.

Figures

Fig. 1.
The structure of (I), with displacement ellipsoids for non-H atoms drawn at the 50% probability level.
Fig. 2.
A packing diagram for (I), with hydrogen bonds drawn as dashed lines.

Crystal data

C25H22BrN3O5SF(000) = 1136
Mr = 556.43Dx = 1.471 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1629 reflections
a = 11.102 (2) Åθ = 2.2–19.4°
b = 10.336 (2) ŵ = 1.76 mm1
c = 22.160 (4) ÅT = 294 K
β = 98.81 (3)°Block, yellow
V = 2512.9 (8) Å30.24 × 0.20 × 0.12 mm
Z = 4

Data collection

Bruker SMART APEX CCD diffractometer4431 independent reflections
Radiation source: fine-focus sealed tube2007 reflections with I > 2σ(I)
graphiteRint = 0.080
[var phi] and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −8→13
Tmin = 0.628, Tmax = 0.810k = −12→11
12656 measured reflectionsl = −26→25

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.163w = 1/[σ2(Fo2) + (0.0562P)2 + 2.7821P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
4431 reflectionsΔρmax = 0.98 e Å3
320 parametersΔρmin = −0.82 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0027 (4)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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)

xyzUiso*/Ueq
Br1−0.02396 (8)−0.56145 (7)0.12388 (5)0.1174 (5)
S1−0.05698 (13)0.05809 (14)0.13190 (8)0.0487 (4)
N10.3100 (4)0.3198 (4)0.0051 (2)0.0395 (11)
N20.4162 (4)0.4909 (4)−0.1195 (2)0.0452 (12)
N30.3891 (4)0.5927 (4)−0.0811 (2)0.0417 (12)
O1−0.1268 (4)0.1008 (4)0.1771 (2)0.0718 (13)
O2−0.0793 (3)0.1107 (4)0.07154 (18)0.0615 (12)
O30.0813 (3)0.0930 (3)0.16212 (16)0.0422 (9)
O40.2066 (3)−0.1252 (3)0.19075 (17)0.0508 (10)
O50.4261 (3)0.2660 (3)−0.11424 (18)0.0584 (11)
C1−0.0754 (5)−0.1852 (6)0.1783 (3)0.0611 (18)
H1−0.0927−0.14400.21330.073*
C2−0.0685 (6)−0.3191 (7)0.1770 (4)0.070 (2)
H2−0.0824−0.36820.21040.084*
C3−0.0402 (6)−0.3780 (7)0.1246 (4)0.071 (2)
C4−0.0228 (6)−0.3070 (7)0.0741 (4)0.069 (2)
H4−0.0055−0.34830.03920.083*
C5−0.0314 (5)−0.1730 (6)0.0759 (3)0.0566 (17)
H5−0.0200−0.12400.04200.068*
C6−0.0571 (5)−0.1124 (5)0.1284 (3)0.0449 (15)
C70.1760 (4)0.0594 (5)0.1284 (2)0.0356 (13)
C80.2399 (4)−0.0569 (5)0.1435 (2)0.0370 (13)
C90.3316 (5)−0.0897 (5)0.1096 (3)0.0421 (14)
H90.3750−0.16630.11780.050*
C100.3579 (5)−0.0081 (5)0.0636 (3)0.0449 (15)
H100.4177−0.03310.04080.054*
C110.2986 (4)0.1100 (5)0.0501 (2)0.0379 (13)
C120.2050 (5)0.1420 (5)0.0842 (2)0.0388 (14)
H120.16280.21950.07670.047*
C130.2697 (5)−0.2459 (5)0.2063 (3)0.0636 (18)
H13A0.2586−0.30220.17140.095*
H13B0.2374−0.28630.23940.095*
H13C0.3551−0.22920.21840.095*
C140.3353 (5)0.1982 (5)0.0048 (3)0.0429 (14)
H140.37790.1660−0.02500.052*
C150.3472 (4)0.4037 (5)−0.0382 (2)0.0361 (13)
C160.3973 (5)0.3721 (5)−0.0931 (3)0.0403 (14)
C170.3399 (5)0.5359 (5)−0.0341 (2)0.0406 (14)
C180.2903 (5)0.6155 (5)0.0127 (3)0.0573 (17)
H18A0.25460.55970.03970.086*
H18B0.22930.6736−0.00720.086*
H18C0.35500.66450.03570.086*
C190.3517 (6)0.7179 (5)−0.1087 (3)0.0663 (19)
H19A0.28170.7063−0.13940.099*
H19B0.41730.7539−0.12690.099*
H19C0.33170.7757−0.07780.099*
C200.4861 (5)0.5129 (5)−0.1677 (3)0.0415 (14)
C210.4518 (5)0.4494 (5)−0.2229 (3)0.0518 (16)
H210.38470.3944−0.22800.062*
C220.5180 (6)0.4683 (6)−0.2703 (3)0.0634 (19)
H220.49580.4249−0.30710.076*
C230.6173 (7)0.5514 (7)−0.2633 (3)0.074 (2)
H230.66010.5658−0.29570.089*
C240.6519 (6)0.6123 (6)−0.2083 (3)0.0669 (19)
H240.71960.6664−0.20340.080*
C250.5879 (5)0.5945 (5)−0.1599 (3)0.0543 (16)
H250.61210.6362−0.12290.065*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.1074 (7)0.0431 (5)0.1895 (12)0.0027 (4)−0.0163 (6)−0.0076 (5)
S10.0404 (9)0.0425 (8)0.0666 (12)0.0128 (7)0.0188 (8)0.0081 (8)
N10.038 (3)0.042 (3)0.040 (3)−0.002 (2)0.007 (2)0.008 (2)
N20.054 (3)0.035 (3)0.053 (3)0.006 (2)0.027 (3)0.001 (2)
N30.050 (3)0.031 (3)0.046 (3)0.008 (2)0.013 (2)0.005 (2)
O10.063 (3)0.065 (3)0.099 (4)0.025 (2)0.048 (3)0.002 (3)
O20.057 (3)0.067 (3)0.060 (3)0.015 (2)0.006 (2)0.032 (2)
O30.041 (2)0.037 (2)0.052 (3)0.0062 (16)0.0158 (18)−0.0046 (18)
O40.051 (2)0.047 (2)0.054 (3)0.0093 (18)0.010 (2)0.016 (2)
O50.074 (3)0.039 (2)0.068 (3)0.006 (2)0.031 (2)−0.004 (2)
C10.058 (4)0.056 (4)0.073 (5)0.000 (3)0.020 (4)0.008 (4)
C20.062 (5)0.053 (5)0.093 (6)−0.006 (3)0.005 (4)0.027 (4)
C30.049 (4)0.049 (4)0.107 (7)0.000 (3)−0.012 (4)−0.004 (5)
C40.060 (5)0.061 (5)0.081 (6)0.007 (3)−0.007 (4)−0.021 (4)
C50.046 (4)0.064 (5)0.055 (5)0.001 (3)−0.008 (3)−0.001 (4)
C60.039 (3)0.038 (3)0.057 (4)0.001 (3)0.006 (3)0.007 (3)
C70.039 (3)0.029 (3)0.039 (3)0.006 (2)0.005 (3)−0.001 (3)
C80.036 (3)0.031 (3)0.043 (4)−0.001 (2)0.003 (3)0.005 (3)
C90.039 (3)0.029 (3)0.057 (4)0.009 (2)0.003 (3)−0.004 (3)
C100.041 (3)0.042 (3)0.056 (4)0.007 (3)0.019 (3)−0.001 (3)
C110.034 (3)0.037 (3)0.044 (4)−0.001 (2)0.009 (3)0.001 (3)
C120.040 (3)0.028 (3)0.047 (4)0.003 (2)0.004 (3)0.000 (3)
C130.069 (4)0.045 (4)0.076 (5)0.014 (3)0.009 (3)0.020 (4)
C140.040 (4)0.044 (3)0.048 (4)0.003 (3)0.017 (3)0.002 (3)
C150.030 (3)0.035 (3)0.044 (4)0.005 (2)0.007 (3)−0.001 (3)
C160.039 (3)0.034 (3)0.049 (4)0.002 (3)0.010 (3)0.003 (3)
C170.041 (3)0.040 (3)0.040 (4)0.004 (3)0.003 (3)0.001 (3)
C180.066 (4)0.048 (4)0.061 (4)0.008 (3)0.016 (3)−0.001 (3)
C190.085 (5)0.041 (4)0.078 (5)0.018 (3)0.029 (4)0.016 (3)
C200.043 (4)0.042 (3)0.040 (4)0.008 (3)0.009 (3)0.007 (3)
C210.052 (4)0.056 (4)0.048 (4)0.011 (3)0.009 (3)0.004 (3)
C220.074 (5)0.077 (5)0.040 (4)0.028 (4)0.010 (4)0.004 (4)
C230.082 (5)0.089 (5)0.061 (5)0.024 (5)0.040 (4)0.031 (5)
C240.060 (4)0.074 (5)0.071 (5)−0.003 (3)0.023 (4)0.012 (4)
C250.057 (4)0.054 (4)0.054 (4)−0.003 (3)0.016 (3)0.004 (3)

Geometric parameters (Å, °)

Br1—C31.905 (7)C9—H90.9300
S1—O11.427 (4)C10—C111.398 (7)
S1—O21.430 (4)C10—H100.9300
S1—O31.619 (4)C11—C121.415 (7)
S1—C61.764 (6)C11—C141.461 (7)
N1—C141.287 (6)C12—H120.9300
N1—C151.403 (6)C13—H13A0.9600
N2—C161.390 (6)C13—H13B0.9600
N2—N31.414 (6)C13—H13C0.9600
N2—C201.433 (7)C14—H140.9300
N3—C171.378 (6)C15—C171.373 (7)
N3—C191.464 (6)C15—C161.449 (7)
O3—C71.423 (6)C17—C181.495 (7)
O4—C81.359 (6)C18—H18A0.9600
O4—C131.446 (6)C18—H18B0.9600
O5—C161.253 (6)C18—H18C0.9600
C1—C61.378 (8)C19—H19A0.9600
C1—C21.386 (8)C19—H19B0.9600
C1—H10.9300C19—H19C0.9600
C2—C31.389 (9)C20—C211.388 (7)
C2—H20.9300C20—C251.399 (7)
C3—C41.375 (9)C21—C221.386 (8)
C4—C51.389 (8)C21—H210.9300
C4—H40.9300C22—C231.387 (9)
C5—C61.388 (8)C22—H220.9300
C5—H50.9300C23—C241.374 (9)
C7—C121.374 (7)C23—H230.9300
C7—C81.410 (6)C24—C251.386 (8)
C8—C91.397 (7)C24—H240.9300
C9—C101.388 (7)C25—H250.9300
O1—S1—O2120.2 (3)C11—C12—H12119.8
O1—S1—O3102.9 (2)O4—C13—H13A109.5
O2—S1—O3108.7 (2)O4—C13—H13B109.5
O1—S1—C6110.1 (3)H13A—C13—H13B109.5
O2—S1—C6109.9 (3)O4—C13—H13C109.5
O3—S1—C6103.6 (2)H13A—C13—H13C109.5
C14—N1—C15120.8 (5)H13B—C13—H13C109.5
C16—N2—N3110.2 (4)N1—C14—C11121.4 (5)
C16—N2—C20126.0 (4)N1—C14—H14119.3
N3—N2—C20121.4 (4)C11—C14—H14119.3
C17—N3—N2106.4 (4)C17—C15—N1122.9 (5)
C17—N3—C19124.9 (4)C17—C15—C16108.3 (5)
N2—N3—C19118.6 (4)N1—C15—C16128.7 (4)
C7—O3—S1117.3 (3)O5—C16—N2123.5 (5)
C8—O4—C13116.9 (4)O5—C16—C15131.6 (5)
C6—C1—C2120.9 (7)N2—C16—C15104.8 (4)
C6—C1—H1119.6C15—C17—N3109.9 (5)
C2—C1—H1119.6C15—C17—C18128.7 (5)
C1—C2—C3118.4 (7)N3—C17—C18121.4 (5)
C1—C2—H2120.8C17—C18—H18A109.5
C3—C2—H2120.8C17—C18—H18B109.5
C4—C3—C2121.5 (7)H18A—C18—H18B109.5
C4—C3—Br1119.9 (6)C17—C18—H18C109.5
C2—C3—Br1118.5 (6)H18A—C18—H18C109.5
C3—C4—C5119.3 (7)H18B—C18—H18C109.5
C3—C4—H4120.3N3—C19—H19A109.5
C5—C4—H4120.3N3—C19—H19B109.5
C6—C5—C4119.8 (6)H19A—C19—H19B109.5
C6—C5—H5120.1N3—C19—H19C109.5
C4—C5—H5120.1H19A—C19—H19C109.5
C1—C6—C5120.0 (6)H19B—C19—H19C109.5
C1—C6—S1120.6 (5)C21—C20—C25120.1 (5)
C5—C6—S1119.3 (5)C21—C20—N2118.4 (5)
C12—C7—C8122.4 (5)C25—C20—N2121.5 (5)
C12—C7—O3119.6 (4)C22—C21—C20119.7 (6)
C8—C7—O3117.9 (4)C22—C21—H21120.2
O4—C8—C9126.5 (5)C20—C21—H21120.2
O4—C8—C7116.1 (5)C21—C22—C23120.5 (6)
C9—C8—C7117.4 (5)C21—C22—H22119.7
C10—C9—C8120.0 (5)C23—C22—H22119.7
C10—C9—H9120.0C24—C23—C22119.4 (6)
C8—C9—H9120.0C24—C23—H23120.3
C9—C10—C11122.9 (5)C22—C23—H23120.3
C9—C10—H10118.6C23—C24—C25121.3 (6)
C11—C10—H10118.6C23—C24—H24119.4
C10—C11—C12116.8 (5)C25—C24—H24119.4
C10—C11—C14121.4 (5)C24—C25—C20119.0 (6)
C12—C11—C14121.8 (5)C24—C25—H25120.5
C7—C12—C11120.4 (5)C20—C25—H25120.5
C7—C12—H12119.8
C16—N2—N3—C17−6.8 (5)O3—C7—C12—C11−179.8 (4)
C20—N2—N3—C17−170.1 (5)C10—C11—C12—C70.3 (7)
C16—N2—N3—C19−154.0 (5)C14—C11—C12—C7−177.2 (5)
C20—N2—N3—C1942.7 (7)C15—N1—C14—C11179.2 (4)
O1—S1—O3—C7178.7 (3)C10—C11—C14—N1−158.1 (5)
O2—S1—O3—C7−52.8 (4)C12—C11—C14—N119.3 (8)
C6—S1—O3—C764.0 (4)C14—N1—C15—C17−169.3 (5)
C6—C1—C2—C31.2 (10)C14—N1—C15—C1611.0 (8)
C1—C2—C3—C4−1.9 (10)N3—N2—C16—O5−172.4 (5)
C1—C2—C3—Br1177.4 (5)C20—N2—C16—O5−10.1 (9)
C2—C3—C4—C51.2 (10)N3—N2—C16—C154.5 (5)
Br1—C3—C4—C5−178.1 (4)C20—N2—C16—C15166.9 (5)
C3—C4—C5—C60.2 (9)C17—C15—C16—O5175.9 (6)
C2—C1—C6—C50.1 (9)N1—C15—C16—O5−4.3 (9)
C2—C1—C6—S1−176.2 (5)C17—C15—C16—N2−0.6 (6)
C4—C5—C6—C1−0.8 (8)N1—C15—C16—N2179.1 (5)
C4—C5—C6—S1175.5 (4)N1—C15—C17—N3176.6 (4)
O1—S1—C6—C1−25.1 (6)C16—C15—C17—N3−3.6 (6)
O2—S1—C6—C1−159.7 (4)N1—C15—C17—C18−2.3 (9)
O3—S1—C6—C184.3 (5)C16—C15—C17—C18177.5 (5)
O1—S1—C6—C5158.6 (4)N2—N3—C17—C156.3 (6)
O2—S1—C6—C524.0 (5)C19—N3—C17—C15150.8 (5)
O3—S1—C6—C5−91.9 (5)N2—N3—C17—C18−174.7 (5)
S1—O3—C7—C1284.6 (5)C19—N3—C17—C18−30.1 (8)
S1—O3—C7—C8−97.6 (5)C16—N2—C20—C2159.0 (7)
C13—O4—C8—C9−2.1 (7)N3—N2—C20—C21−140.4 (5)
C13—O4—C8—C7179.0 (4)C16—N2—C20—C25−120.0 (6)
C12—C7—C8—O4175.9 (5)N3—N2—C20—C2540.6 (7)
O3—C7—C8—O4−1.8 (7)C25—C20—C21—C22−0.7 (8)
C12—C7—C8—C9−3.1 (7)N2—C20—C21—C22−179.7 (5)
O3—C7—C8—C9179.2 (4)C20—C21—C22—C23−0.8 (9)
O4—C8—C9—C10−178.0 (5)C21—C22—C23—C241.9 (9)
C7—C8—C9—C100.9 (7)C22—C23—C24—C25−1.5 (10)
C8—C9—C10—C111.9 (8)C23—C24—C25—C200.0 (9)
C9—C10—C11—C12−2.5 (8)C21—C20—C25—C241.1 (8)
C9—C10—C11—C14175.0 (5)N2—C20—C25—C24−179.9 (5)
C8—C7—C12—C112.5 (8)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C14—H14···O50.932.363.046 (7)130
C9—H9···O5i0.932.453.238 (6)143

Symmetry codes: (i) −x+1, −y, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5442).

References

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  • Chen, X. & Yu, M. (2006). Acta Cryst. E62, o4592–o4593.
  • Santos, M. L. P., Bagatin, I. A., Pereira, E. M. & Ferreira, A. M. D. C. (2001). J. Chem. Soc. Dalton Trans. pp. 838–844.
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  • Zhang, Q.-Z., Zhao, Y.-L., Chen, X. & Yu, M. (2006). Acta Cryst. E62, o5252–o5254.

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