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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): o2116.
Published online 2009 August 8. doi:  10.1107/S160053680902950X
PMCID: PMC2970147

4-{(Z)-(sec-Butyl­amino)(phen­yl)methyl­ene}-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Abstract

In the title compound, C21H23N3O, the dihedral angles formed by the pyrazolone ring with two phenyl rings are 10.38 (8) and 76.94 (6)°. The sec-butyl­amino group is disordered over two positions, with refined site-occupancy factors of 0.730 (4) and 0.270 (4). The compound could potentially be ligand stabilized in the solid state in a keto–enamine tautomeric form. The amine functionality is involved in an intra­molecular N—H(...)O hydrogen bond, while weak inter­molecular C—H(...)O and C—H(...)N hydrogen bonds participate in the formation of the crystal structure.

Related literature

For the anti­bacterial, biological and analgesic activity of metal complexes of 1-phenyl-3-methyl-4-benzoyl­pyrazolon-5-one, see: Li et al. (1997 [triangle]); Liu et al. (1980 [triangle]); Zhou et al. (1999 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2116-scheme1.jpg

Experimental

Crystal data

  • C21H23N3O
  • M r = 333.42
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2116-efi1.jpg
  • a = 9.3631 (19) Å
  • b = 10.077 (2) Å
  • c = 10.687 (2) Å
  • α = 107.07 (3)°
  • β = 100.30 (3)°
  • γ = 100.14 (3)°
  • V = 920.0 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 113 K
  • 0.20 × 0.18 × 0.16 mm

Data collection

  • Rigaku Saturn CCD area-detector diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.985, T max = 0.988
  • 8309 measured reflections
  • 4296 independent reflections
  • 2944 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.135
  • S = 1.08
  • 4296 reflections
  • 272 parameters
  • 16 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.32 e Å−3
  • Δρmin = −0.21 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; 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
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680902950X/bh2238sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902950X/bh2238Isup2.hkl

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

Acknowledgments

The authors gratefully acknowledge financial support from the National Natural Science Foundation of China (grant No. 20772066).

supplementary crystallographic information

Comment

1-Phenyl-3-methyl-4-benzoylpyrazolon-5-one (HPMBP), an effective β-diketonate, is widely used and well known for its extractive ability. In recent years, HPMBP and its metal complexes have also been found to have good antibacterial and biological properties. Its metal complexes have analgesic activity (Liu et al., 1980; Li et al., 1997; Zhou et al., 1999). In order to develop new medicines, we have synthesized the title compound, (I), and its structure is reported here.

The structure of (I) is shown in Fig. 1. The dihedral angles formed by the pyrazolone ring with the two phenyl rings C1···C6 and C12···C17 are 10.38 (8) and 76.94 (6)°, respectively. The O atom of the 3-methyl-1-phenylpyrazol-5-one moiety and the N atom of the sec-butylamino group are available for coordination with metals. The pyrazole ring is planar and atoms O1, C7, C8, C11 and N3 (or N3') are almost coplanar, the largest deviation being 0.0323 (13) Å [or 0.201 (3) Å] for atom C11. The dihedral angle between this mean plane and the pyrazoline ring of PMBP is 3.00 (11)° [or 12.10 (18)°]. The bond lengths within this part of the molecule (Table 1) lie between classical single- and double-bond lengths, indicating extensive conjugation. A strong intramolecular N3—H3···O1 hydrogen bond (Table 2) is observed, leading to a keto-enamine form. The molecule is further stabilized by C—H···O and C—H···N intramolecular hydrogen bonds (Table 2), while the crystal structure includes C—H···O and C—H···N intermolecular hydrogen bonds (Table 2 and Fig. 2).

Experimental

Compound (I) was synthesized by refluxing a mixture of 1-phenyl-3- methyl-4-benzoylpyrazol-5-one (10 mmol) and sec-butylamine (10 mmol) in ethanol (80 ml) over a steam bath for about 4 h. Excess solvent was removed by evaporation and the solution was cooled to room temperature. After 2 days a yellow solid was obtained and this was dried in air. The product was recrystallized from ethanol, to afford yellow crystals of (I) suitable for X-ray analysis.

Refinement

The sec-butylamino group shows positional disorder. At the final stage of the refinement, the occupancy factors of two possible sites, N3/C18/C19/C20/C21 and N3'/C18'/C19'/C20'/C21', converged to 0.730 (4) and 0.270 (4), respectively. The geometry of this disordered group was regularized using 16 restraints. C-bonded H atoms were positioned geometrically, with C—H = 0.95–1.00 Å and amine H atoms (H3 and H3') were found in a difference map. Amine H atoms were refined freely, while C-bonded H atoms were included in the final cycles of refinement using a riding model, with Uiso(H) = 1.2Ueq(CH2 and CH) or 1.5Ueq(CH3).

Figures

Fig. 1.
View of the title compound, with displacement ellipsoids drawn at the 30% probability level.
Fig. 2.
Intermolecular hydrogen bonds (dashed line) in the structure of (I).

Crystal data

C21H23N3OZ = 2
Mr = 333.42F(000) = 356
Triclinic, P1Dx = 1.204 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.3631 (19) ÅCell parameters from 2809 reflections
b = 10.077 (2) Åθ = 2.2–27.9°
c = 10.687 (2) ŵ = 0.08 mm1
α = 107.07 (3)°T = 113 K
β = 100.30 (3)°Block, yellow
γ = 100.14 (3)°0.20 × 0.18 × 0.16 mm
V = 920.0 (4) Å3

Data collection

Rigaku Saturn CCD area-detector diffractometer4296 independent reflections
Radiation source: rotating anode2944 reflections with I > 2σ(I)
confocalRint = 0.026
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 2.2°
ω and [var phi] scansh = −12→12
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)k = −11→13
Tmin = 0.985, Tmax = 0.988l = −14→13
8309 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.135w = 1/[σ2(Fo2) + (0.0708P)2 + 0.0483P] where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.005
4296 reflectionsΔρmax = 0.32 e Å3
272 parametersΔρmin = −0.21 e Å3
16 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraintsExtinction coefficient: 0.155 (17)
Primary atom site location: structure-invariant direct methods

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
O10.22643 (10)0.11615 (12)0.45573 (9)0.0366 (3)
N10.35369 (12)0.31219 (12)0.64961 (11)0.0281 (3)
N20.49444 (13)0.40916 (13)0.69807 (12)0.0337 (3)
C10.25255 (16)0.31996 (14)0.73383 (13)0.0273 (3)
C20.10503 (16)0.24104 (16)0.68465 (15)0.0331 (3)
H2A0.07050.17940.59340.040*
C30.00826 (17)0.25261 (16)0.76926 (16)0.0377 (4)
H3A−0.09260.19820.73550.045*
C40.05684 (19)0.34266 (16)0.90262 (16)0.0385 (4)
H4A−0.01030.35100.95990.046*
C50.20343 (19)0.41966 (16)0.95079 (15)0.0387 (4)
H5A0.23770.48061.04230.046*
C60.30202 (17)0.40978 (15)0.86797 (14)0.0332 (3)
H6A0.40290.46400.90250.040*
C70.33879 (15)0.21606 (14)0.52318 (13)0.0261 (3)
C80.47946 (14)0.25477 (14)0.49077 (13)0.0260 (3)
C90.56792 (16)0.37451 (14)0.60449 (14)0.0293 (3)
C100.72210 (17)0.46179 (17)0.62636 (16)0.0402 (4)
H10A0.75090.53660.71530.060*
H10B0.72440.50610.55620.060*
H10C0.79240.40000.62200.060*
C110.50824 (15)0.17900 (16)0.36892 (14)0.0325 (4)
C120.65777 (15)0.20895 (15)0.33908 (13)0.0282 (3)
C130.70609 (16)0.32385 (15)0.29807 (14)0.0321 (3)
H13A0.64240.38500.28570.039*
C140.84815 (17)0.34901 (16)0.27525 (15)0.0359 (4)
H14A0.88230.42820.24810.043*
C150.93991 (16)0.25914 (16)0.29191 (15)0.0352 (4)
H15A1.03710.27690.27640.042*
C160.89140 (16)0.14361 (16)0.33096 (15)0.0354 (4)
H16A0.95460.08140.34110.042*
C170.75037 (16)0.11839 (16)0.35532 (15)0.0336 (4)
H17A0.71700.03940.38310.040*
N30.4045 (2)0.0595 (2)0.2841 (2)0.0280 (5)0.730 (4)
H30.3183 (15)0.043 (2)0.310 (2)0.033 (5)*0.730 (4)
C180.4079 (7)−0.1799 (5)0.1378 (6)0.0449 (11)0.730 (4)
H18A0.5018−0.17930.19600.067*0.730 (4)
H18B0.4014−0.23650.04420.067*0.730 (4)
H18C0.3232−0.22220.16740.067*0.730 (4)
C190.4035 (2)−0.0265 (2)0.14681 (18)0.0280 (6)0.730 (4)
H190.49400.01750.12220.034*0.730 (4)
C200.2651 (2)−0.0251 (3)0.0494 (2)0.0409 (7)0.730 (4)
H20A0.1751−0.06640.07470.049*0.730 (4)
H20B0.2624−0.0866−0.04270.049*0.730 (4)
C210.2595 (8)0.1239 (7)0.0476 (11)0.0692 (17)0.730 (4)
H21A0.24950.18210.13540.104*0.730 (4)
H21B0.17350.1176−0.02320.104*0.730 (4)
H21C0.35180.16840.02950.104*0.730 (4)
N3'0.3875 (6)0.1202 (8)0.2699 (5)0.0319 (14)0.270 (4)
H3'0.300 (3)0.126 (6)0.294 (5)0.033 (5)*0.270 (4)
C18'0.297 (3)0.1380 (19)0.049 (3)0.0692 (17)0.270 (4)
H18D0.19660.13060.06620.104*0.270 (4)
H18E0.28740.0952−0.04800.104*0.270 (4)
H18F0.35020.23900.07970.104*0.270 (4)
C19'0.3832 (6)0.0589 (6)0.1254 (4)0.0332 (17)0.270 (4)
H19'0.48760.07230.11320.040*0.270 (4)
C20'0.3103 (7)−0.0988 (6)0.0803 (6)0.0424 (19)0.270 (4)
H20C0.3058−0.1420−0.01680.051*0.270 (4)
H20D0.2063−0.11090.09050.051*0.270 (4)
C21'0.391 (2)−0.1790 (15)0.1582 (19)0.0449 (11)0.270 (4)
H21D0.4973−0.15890.15730.067*0.270 (4)
H21E0.3467−0.28200.11600.067*0.270 (4)
H21F0.3820−0.14790.25170.067*0.270 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0214 (5)0.0490 (6)0.0292 (5)−0.0004 (4)0.0063 (4)0.0034 (4)
N10.0238 (6)0.0280 (6)0.0298 (6)0.0032 (5)0.0074 (5)0.0070 (5)
N20.0286 (7)0.0283 (6)0.0382 (7)0.0003 (5)0.0107 (5)0.0047 (5)
C10.0295 (7)0.0259 (7)0.0307 (7)0.0102 (5)0.0121 (6)0.0109 (5)
C20.0309 (8)0.0336 (8)0.0338 (7)0.0073 (6)0.0117 (6)0.0078 (6)
C30.0328 (8)0.0373 (8)0.0440 (8)0.0071 (6)0.0174 (7)0.0114 (7)
C40.0463 (10)0.0359 (8)0.0423 (8)0.0144 (7)0.0254 (7)0.0149 (7)
C50.0504 (10)0.0354 (8)0.0321 (7)0.0123 (7)0.0169 (7)0.0088 (6)
C60.0346 (8)0.0325 (8)0.0320 (7)0.0077 (6)0.0093 (6)0.0096 (6)
C70.0231 (7)0.0311 (7)0.0248 (6)0.0068 (6)0.0051 (5)0.0105 (5)
C80.0216 (7)0.0303 (7)0.0272 (7)0.0065 (5)0.0054 (5)0.0113 (6)
C90.0267 (7)0.0266 (7)0.0339 (7)0.0047 (6)0.0079 (6)0.0099 (6)
C100.0342 (9)0.0356 (8)0.0400 (8)−0.0042 (7)0.0107 (7)0.0031 (7)
C110.0228 (7)0.0447 (9)0.0275 (7)0.0034 (6)0.0054 (6)0.0116 (6)
C120.0213 (7)0.0356 (8)0.0247 (6)0.0028 (6)0.0053 (5)0.0082 (6)
C130.0306 (8)0.0326 (7)0.0357 (7)0.0100 (6)0.0108 (6)0.0123 (6)
C140.0345 (8)0.0323 (8)0.0414 (8)0.0028 (6)0.0152 (7)0.0127 (6)
C150.0206 (7)0.0378 (8)0.0409 (8)0.0011 (6)0.0092 (6)0.0061 (6)
C160.0223 (7)0.0378 (8)0.0419 (8)0.0082 (6)0.0016 (6)0.0105 (7)
C170.0274 (8)0.0366 (8)0.0353 (7)0.0018 (6)0.0023 (6)0.0166 (6)
N30.0215 (10)0.0311 (11)0.0271 (9)0.0031 (9)0.0079 (7)0.0040 (8)
C180.054 (2)0.0336 (9)0.048 (2)0.0125 (9)0.0204 (15)0.0082 (11)
C190.0251 (11)0.0284 (12)0.0262 (10)0.0039 (9)0.0080 (8)0.0032 (8)
C200.0368 (13)0.0511 (15)0.0311 (11)0.0160 (11)0.0051 (10)0.0071 (10)
C210.096 (5)0.0693 (18)0.0589 (14)0.044 (2)0.019 (3)0.0321 (16)
N3'0.023 (3)0.043 (4)0.028 (3)0.012 (3)0.007 (2)0.007 (3)
C18'0.096 (5)0.0693 (18)0.0589 (14)0.044 (2)0.019 (3)0.0321 (16)
C19'0.025 (3)0.046 (4)0.031 (3)0.006 (3)0.011 (2)0.015 (3)
C20'0.035 (4)0.043 (4)0.039 (3)0.000 (3)0.008 (3)0.007 (3)
C21'0.054 (2)0.0336 (9)0.048 (2)0.0125 (9)0.0204 (15)0.0082 (11)

Geometric parameters (Å, °)

O1—C71.2529 (17)C16—C171.386 (2)
N1—C71.3785 (18)C16—H16A0.9500
N1—N21.4019 (17)C17—H17A0.9500
N1—C11.4150 (18)N3—C191.466 (3)
N2—C91.3119 (19)N3—H30.902 (10)
C1—C21.387 (2)N3—H3'1.28 (4)
C1—C61.394 (2)C18—C191.528 (4)
C2—C31.386 (2)C18—H18A0.9800
C2—H2A0.9500C18—H18B0.9800
C3—C41.387 (2)C18—H18C0.9800
C3—H3A0.9500C19—C201.516 (3)
C4—C51.374 (2)C19—H191.0000
C4—H4A0.9500C20—C211.517 (5)
C5—C61.385 (2)C20—H20A0.9900
C5—H5A0.9500C20—H20B0.9900
C6—H6A0.9500C21—H21A0.9800
C7—C81.4382 (19)C21—H21B0.9800
C8—C111.402 (2)C21—H21C0.9800
C8—C91.430 (2)N3'—C19'1.475 (6)
C9—C101.491 (2)N3'—H31.149 (18)
C10—H10A0.9800N3'—H3'0.904 (10)
C10—H10B0.9800C18'—C19'1.527 (9)
C10—H10C0.9800C18'—H18D0.9800
C11—N3'1.311 (5)C18'—H18E0.9800
C11—N31.359 (2)C18'—H18F0.9800
C11—C121.4901 (19)C19'—C20'1.508 (7)
C12—C131.386 (2)C19'—H19'1.0000
C12—C171.390 (2)C20'—C21'1.519 (9)
C13—C141.388 (2)C20'—H20C0.9900
C13—H13A0.9500C20'—H20D0.9900
C14—C151.380 (2)C21'—H21D0.9800
C14—H14A0.9500C21'—H21E0.9800
C15—C161.379 (2)C21'—H21F0.9800
C15—H15A0.9500
C7—N1—N2111.72 (11)C15—C16—C17119.92 (14)
C7—N1—C1129.43 (12)C15—C16—H16A120.0
N2—N1—C1118.78 (11)C17—C16—H16A120.0
C9—N2—N1106.50 (11)C16—C17—C12119.82 (14)
C2—C1—C6119.64 (14)C16—C17—H17A120.1
C2—C1—N1121.12 (12)C12—C17—H17A120.1
C6—C1—N1119.24 (13)C11—N3—C19128.01 (18)
C3—C2—C1119.69 (14)C11—N3—H3114.1 (14)
C3—C2—H2A120.2C19—N3—H3116.6 (13)
C1—C2—H2A120.2C11—N3—H3'91 (2)
C2—C3—C4120.83 (14)C19—N3—H3'116 (2)
C2—C3—H3A119.6H3—N3—H3'47 (2)
C4—C3—H3A119.6N3—C19—C20109.15 (17)
C5—C4—C3119.10 (15)N3—C19—C18111.0 (3)
C5—C4—H4A120.4C20—C19—C18110.6 (3)
C3—C4—H4A120.4N3—C19—H19108.7
C4—C5—C6121.02 (14)C20—C19—H19108.7
C4—C5—H5A119.5C18—C19—H19108.7
C6—C5—H5A119.5C19—C20—C21113.0 (3)
C5—C6—C1119.71 (14)C19—C20—H20A109.0
C5—C6—H6A120.1C21—C20—H20A109.0
C1—C6—H6A120.1C19—C20—H20B109.0
O1—C7—N1126.01 (13)C21—C20—H20B109.0
O1—C7—C8129.17 (13)H20A—C20—H20B107.8
N1—C7—C8104.80 (12)C11—N3'—C19'126.0 (5)
C11—C8—C9132.65 (13)C11—N3'—H3102.0 (11)
C11—C8—C7121.77 (13)C19'—N3'—H3113.7 (11)
C9—C8—C7105.58 (12)C11—N3'—H3'115 (4)
N2—C9—C8111.40 (13)C19'—N3'—H3'119 (4)
N2—C9—C10118.92 (13)H3—N3'—H3'52 (4)
C8—C9—C10129.65 (14)C19'—C18'—H18D109.5
C9—C10—H10A109.5C19'—C18'—H18E109.5
C9—C10—H10B109.5H18D—C18'—H18E109.5
H10A—C10—H10B109.5C19'—C18'—H18F109.5
C9—C10—H10C109.5H18D—C18'—H18F109.5
H10A—C10—H10C109.5H18E—C18'—H18F109.5
H10B—C10—H10C109.5N3'—C19'—C20'107.5 (5)
N3'—C11—C8113.3 (3)N3'—C19'—C18'108.1 (14)
N3—C11—C8118.82 (15)C20'—C19'—C18'112.7 (8)
N3'—C11—C12120.1 (3)N3'—C19'—H19'109.5
N3—C11—C12117.86 (15)C20'—C19'—H19'109.5
C8—C11—C12122.46 (13)C18'—C19'—H19'109.5
C13—C12—C17120.12 (13)C19'—C20'—C21'113.7 (7)
C13—C12—C11122.04 (13)C19'—C20'—H20C108.8
C17—C12—C11117.84 (13)C21'—C20'—H20C108.8
C12—C13—C14119.60 (14)C19'—C20'—H20D108.8
C12—C13—H13A120.2C21'—C20'—H20D108.8
C14—C13—H13A120.2H20C—C20'—H20D107.7
C15—C14—C13120.10 (14)C20'—C21'—H21D109.5
C15—C14—H14A119.9C20'—C21'—H21E109.5
C13—C14—H14A119.9H21D—C21'—H21E109.5
C16—C15—C14120.43 (14)C20'—C21'—H21F109.5
C16—C15—H15A119.8H21D—C21'—H21F109.5
C14—C15—H15A119.8H21E—C21'—H21F109.5
C7—N1—N2—C9−0.44 (16)C7—C8—C11—N3−5.0 (2)
C1—N1—N2—C9176.80 (12)C9—C8—C11—C124.8 (2)
C7—N1—C1—C2−12.6 (2)C7—C8—C11—C12−174.22 (13)
N2—N1—C1—C2170.69 (12)N3'—C11—C12—C1376.6 (4)
C7—N1—C1—C6168.11 (13)N3—C11—C12—C13111.8 (2)
N2—N1—C1—C6−8.57 (19)C8—C11—C12—C13−78.87 (19)
C6—C1—C2—C30.2 (2)N3'—C11—C12—C17−104.2 (4)
N1—C1—C2—C3−179.08 (13)N3—C11—C12—C17−69.0 (2)
C1—C2—C3—C40.3 (2)C8—C11—C12—C17100.28 (17)
C2—C3—C4—C5−0.7 (2)C17—C12—C13—C14−0.9 (2)
C3—C4—C5—C60.8 (2)C11—C12—C13—C14178.22 (13)
C4—C5—C6—C1−0.3 (2)C12—C13—C14—C150.7 (2)
C2—C1—C6—C5−0.1 (2)C13—C14—C15—C160.2 (2)
N1—C1—C6—C5179.13 (13)C14—C15—C16—C17−0.8 (2)
N2—N1—C7—O1178.94 (13)C15—C16—C17—C120.6 (2)
C1—N1—C7—O12.1 (2)C13—C12—C17—C160.3 (2)
N2—N1—C7—C80.35 (15)C11—C12—C17—C16−178.90 (13)
C1—N1—C7—C8−176.52 (12)N3'—C11—N3—C1985.3 (6)
O1—C7—C8—C110.6 (2)C8—C11—N3—C19172.81 (19)
N1—C7—C8—C11179.14 (12)C12—C11—N3—C19−17.5 (3)
O1—C7—C8—C9−178.66 (14)C11—N3—C19—C20−118.9 (3)
N1—C7—C8—C9−0.13 (14)C11—N3—C19—C18118.9 (4)
N1—N2—C9—C80.35 (16)N3—C19—C20—C2161.1 (5)
N1—N2—C9—C10178.68 (12)C18—C19—C20—C21−176.5 (5)
C11—C8—C9—N2−179.29 (15)N3—C11—N3'—C19'−85.2 (8)
C7—C8—C9—N2−0.14 (16)C8—C11—N3'—C19'167.1 (5)
C11—C8—C9—C102.6 (3)C12—C11—N3'—C19'9.5 (9)
C7—C8—C9—C10−178.24 (15)C11—N3'—C19'—C20'116.6 (7)
C9—C8—C11—N3'−152.2 (4)C11—N3'—C19'—C18'−121.5 (11)
C7—C8—C11—N3'28.8 (4)N3'—C19'—C20'—C21'−58.9 (10)
C9—C8—C11—N3174.01 (18)C18'—C19'—C20'—C21'−177.9 (17)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3'—H3'···O10.90 (1)1.99 (4)2.705 (6)135 (5)
N3—H3···O10.90 (1)1.93 (2)2.699 (2)142 (2)
C2—H2A···O10.952.292.9243 (19)123
C6—H6A···N20.952.442.777 (2)101
C16—H16A···O1i0.952.533.2743 (19)135
C13—H13A···N2ii0.952.603.537 (2)167

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2238).

References

  • Li, J.-Z., Yu, W.-J. & Du, X.-Y. (1997). Chin. J. Appl. Chem.14, 98–100.
  • Liu, J.-M., Yang, R.-D. & Ma, T.-R. (1980). Chem. J. Chin. Univ.1, 23–29.
  • Rigaku (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zhou, Y.-P., Yang, Zh.-Y., Yu, H.-J. & Yang, R.-D. (1999). Chin. J. Appl. Chem.16, 37–41.

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