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Acta Crystallogr Sect E Struct Rep Online. 2012 March 1; 68(Pt 3): o839.
Published online 2012 February 24. doi:  10.1107/S1600536812007283
PMCID: PMC3297897

1-[5-(2-Chloro­phen­yl)-5-hy­droxy-3-methyl-4,5-dihydro-1H-pyrazol-1-yl]­ethanone

Abstract

The title compound, C12H13ClN2O2, crystallizes with two independent but very similar mol­ecules (A and B) in the asymmetric unit. The pyrazole ring in each mol­ecule has an envelope conformation. The dihedral angle between the pyrazole ring mean plane and the benzene ring is 86.07 (14)° in A and 85.99 (14)° in B. In the crystal, the A and B mol­ecules are linked via a pair of O—H(...)O hydrogen bonds, forming dimers. These dimers are further linked via C—H(...)O inter­actions to form –ABAB– chains propagating along the c-axis direction.

Related literature  

For the bioactivities of 5-hy­droxy­pyrazolines, see: Sauzem et al. (2008 [triangle]); Zhao et al. (2009 [triangle]); Idrees et al. (2009 [triangle]). For the crystal structures of related 5-hy­droxy­pyrazolines, see: Kargar, Kia, Froozandeh et al. (2011 [triangle]); Kargar, Kia, Moghadamm et al. (2011 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-68-0o839-scheme1.jpg

Experimental  

Crystal data  

  • C12H13ClN2O2
  • M r = 252.70
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-68-0o839-efi1.jpg
  • a = 10.320 (3) Å
  • b = 14.916 (4) Å
  • c = 16.346 (4) Å
  • β = 95.158 (3)°
  • V = 2506.0 (12) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.30 mm−1
  • T = 296 K
  • 0.39 × 0.25 × 0.15 mm

Data collection  

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2007 [triangle]) T min = 0.893, T max = 0.957
  • 16979 measured reflections
  • 4663 independent reflections
  • 3077 reflections with I > 2σ(I)
  • R int = 0.038

Refinement  

  • R[F 2 > 2σ(F 2)] = 0.053
  • wR(F 2) = 0.159
  • S = 1.02
  • 4663 reflections
  • 313 parameters
  • H-atom parameters constrained
  • Δρmax = 0.39 e Å−3
  • Δρmin = −0.35 e Å−3

Data collection: SMART (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [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 datablock(s) I, global. DOI: 10.1107/S1600536812007283/su2378sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007283/su2378Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812007283/su2378Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536812007283/su2378Isup4.cml

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

Acknowledgments

This work was supported by the National Natural Science Foundation of China (grant No. 21172057).

supplementary crystallographic information

Comment

5-Hydroxypyrazolines have drawn much attention due to their interesting biological properties such as anti-inflammatory, antibiotic, and hypolipidemic activities (Sauzem et al., 2008; Zhao et al., 2009; Idrees et al., 2009). Crystal structures of some 5-hydroxypyrazoline derivatives have been reported (Kargar, Kia, Froozandeh et al., 2011; Kargar, Kia, Moghadamm et al., 2011). Herein, we report on the crystal structure of the new title 5-hydroxypyrazoline derivative.

The title compound crystallizes with two independent but very similar molecules (A and B) in the asymmetric unit (Fig. 1). All the bond lengths and bond angles are within normal ranges. The five-membered pyrazole rings have envelope conformations with atom C7 as the flap in molecule A, and atom C19 as the flap in molecule B. The dihedral angle between the pyrazole ring mean plane and the phenyl ring is 86.07 (14) ° in A and 85.99 (14) ° in B.

In the crystal, the A and B molecules are linked via a pair of O—H···O hydrogen bonds forming dimers. These dimers are further linked via C-H···O interactions to form -A-B-A-B- chains propagating along the c axis direction (Table 1 and Fig. 2).

Experimental

1-(2-chlorophenyl)butane-1,3-dione (1.0 mmol), acetohydrazide (1.0 mmol), and a drop of concentrated H2SO4 were mixed and ground for 10 min in a mortar. Upon completion of the reaction, monitored by TLC, ethyl acetate and water were added to the reaction mixture. Then, the organic layer was washed with Na2CO3 solution and water, and dried over anhydrous Na2SO4. Ethyl acetate was removed under reduced pressure and the residue was purified by chromatography on silica-gel to provide the title product as a white solid. Colourless block-like crystals of the title compound, suitable for X-ray diffraction analysis, were obtained by slow evaporation of the solvent from a dichloromethane solution at room temperature.

Refinement

The H atoms were included in calculated positions and were refined as riding atoms: O—H = 0.82 Å, and C—H = 0.93, 0.97, 0.96 Å for aromatic, methylene and methyl H atoms, respectively, with Uiso(H) = k ×Ueq(O,C), where k = 1.5 for OH and methyl H atoms, and k = 1.2 for all other H atoms.

Figures

Fig. 1.
Molecular structure of the two independent molecules (A right; B left) of the title compound, with displacement ellipsoids drawn at the 30% probability level.
Fig. 2.
Crystal packing of the title compound, viewed along the a axis. The O—H···O hydrogen bonds and C-H···O interactions are shown as dashed lines (see Table 1 for details; H atoms not involved in these ...

Crystal data

C12H13ClN2O2F(000) = 1056
Mr = 252.70Dx = 1.340 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3669 reflections
a = 10.320 (3) Åθ = 2.4–25.9°
b = 14.916 (4) ŵ = 0.30 mm1
c = 16.346 (4) ÅT = 296 K
β = 95.158 (3)°Block, colourless
V = 2506.0 (12) Å30.39 × 0.25 × 0.15 mm
Z = 8

Data collection

Bruker SMART CCD area-detector diffractometer4663 independent reflections
Radiation source: fine-focus sealed tube3077 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
phi and ω scansθmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2007)h = −12→12
Tmin = 0.893, Tmax = 0.957k = −18→18
16979 measured reflectionsl = −19→19

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0804P)2 + 0.8196P] where P = (Fo2 + 2Fc2)/3
4663 reflections(Δ/σ)max = 0.001
313 parametersΔρmax = 0.39 e Å3
0 restraintsΔρmin = −0.35 e Å3

Special details

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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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)

xyzUiso*/Ueq
C10.5236 (3)0.2945 (2)0.27457 (16)0.0630 (8)
C20.6517 (3)0.32278 (17)0.26911 (14)0.0484 (6)
C30.6858 (3)0.40628 (19)0.30087 (17)0.0643 (8)
H30.77010.42720.29770.077*
C40.5966 (5)0.4597 (2)0.3375 (2)0.0904 (12)
H40.62140.51540.35910.109*
C50.4714 (5)0.4294 (3)0.3415 (2)0.1025 (15)
H50.41120.46530.36500.123*
C60.4349 (4)0.3468 (3)0.3110 (2)0.0891 (12)
H60.35060.32610.31480.107*
C70.7497 (2)0.27082 (16)0.22292 (14)0.0427 (6)
C80.7104 (2)0.26559 (16)0.12996 (14)0.0452 (6)
H8A0.62040.28330.11720.054*
H8B0.76560.30350.09970.054*
C90.7293 (2)0.16951 (17)0.11060 (15)0.0470 (6)
C100.7195 (3)0.1336 (2)0.02506 (16)0.0630 (8)
H10A0.72760.06950.02670.094*
H10B0.78790.1585−0.00400.094*
H10C0.63680.1497−0.00260.094*
C110.7751 (3)0.14051 (18)0.32065 (16)0.0514 (6)
C120.7807 (4)0.0402 (2)0.32863 (19)0.0811 (10)
H12A0.85600.01810.30470.122*
H12B0.70380.01440.30060.122*
H12C0.78570.02400.38570.122*
C130.3110 (3)0.3263 (2)−0.02266 (16)0.0621 (8)
C140.1813 (3)0.34881 (17)−0.01755 (14)0.0470 (6)
C150.1388 (3)0.43010 (17)−0.05224 (17)0.0658 (8)
H150.05290.4476−0.04910.079*
C160.2215 (5)0.4854 (2)−0.0913 (2)0.0941 (13)
H160.19040.5387−0.11510.113*
C170.3479 (5)0.4620 (3)−0.0950 (2)0.1070 (15)
H170.40320.4998−0.12070.128*
C180.3958 (4)0.3819 (3)−0.0606 (2)0.0906 (12)
H180.48250.3659−0.06280.109*
C190.0867 (2)0.29137 (16)0.02655 (14)0.0427 (6)
C200.1250 (2)0.27892 (16)0.11897 (14)0.0459 (6)
H20A0.21420.29750.13350.055*
H20B0.06800.31280.15150.055*
C210.1094 (2)0.18061 (16)0.13134 (15)0.0457 (6)
C220.1166 (3)0.13570 (19)0.21316 (15)0.0564 (7)
H22A0.11150.07190.20570.085*
H22B0.04550.15550.24270.085*
H22C0.19740.15080.24380.085*
C230.0645 (2)0.16960 (16)−0.07964 (15)0.0455 (6)
C240.0633 (3)0.07144 (18)−0.09644 (19)0.0707 (9)
H24A0.05790.0615−0.15470.106*
H24B−0.01060.0447−0.07420.106*
H24C0.14170.0449−0.07120.106*
Cl10.46874 (8)0.19108 (7)0.23531 (5)0.0841 (3)
Cl20.37469 (8)0.22580 (7)0.01857 (5)0.0865 (3)
N10.7575 (2)0.17426 (13)0.24382 (12)0.0457 (5)
N20.7540 (2)0.11902 (14)0.17364 (13)0.0522 (5)
N30.0850 (2)0.19699 (13)−0.00094 (11)0.0443 (5)
N40.0897 (2)0.13575 (14)0.06455 (12)0.0508 (5)
O10.87374 (17)0.30941 (12)0.23266 (10)0.0525 (5)
H10.90880.29680.27820.079*
O20.7846 (2)0.19093 (13)0.37965 (11)0.0621 (5)
O3−0.03948 (17)0.32648 (13)0.01884 (10)0.0548 (5)
H3A−0.07050.3216−0.02890.082*
O40.04921 (19)0.22575 (12)−0.13467 (10)0.0562 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0586 (18)0.090 (2)0.0407 (16)0.0137 (15)0.0055 (13)0.0096 (14)
C20.0569 (16)0.0557 (16)0.0319 (13)0.0083 (12)0.0006 (11)0.0080 (11)
C30.092 (2)0.0540 (17)0.0465 (16)0.0113 (15)0.0059 (15)0.0048 (13)
C40.148 (4)0.068 (2)0.056 (2)0.040 (2)0.015 (2)0.0058 (17)
C50.125 (4)0.124 (4)0.061 (2)0.076 (3)0.025 (2)0.014 (2)
C60.072 (2)0.133 (3)0.064 (2)0.037 (2)0.0174 (17)0.017 (2)
C70.0456 (14)0.0472 (14)0.0348 (13)−0.0022 (10)0.0012 (10)0.0062 (10)
C80.0484 (14)0.0532 (15)0.0333 (13)−0.0031 (11)0.0005 (10)0.0055 (11)
C90.0489 (15)0.0547 (15)0.0366 (13)−0.0019 (11)0.0000 (11)0.0008 (11)
C100.077 (2)0.0695 (18)0.0415 (15)0.0044 (15)−0.0013 (14)−0.0070 (13)
C110.0562 (16)0.0556 (16)0.0412 (15)−0.0062 (12)−0.0019 (12)0.0097 (12)
C120.123 (3)0.0602 (19)0.0563 (18)−0.0050 (18)−0.0099 (19)0.0154 (15)
C130.0633 (19)0.084 (2)0.0388 (15)−0.0168 (15)0.0021 (13)−0.0014 (14)
C140.0620 (17)0.0494 (15)0.0295 (12)−0.0092 (12)0.0039 (11)−0.0054 (10)
C150.103 (2)0.0453 (16)0.0503 (17)−0.0065 (15)0.0106 (16)−0.0037 (13)
C160.161 (4)0.057 (2)0.067 (2)−0.032 (2)0.019 (2)0.0005 (16)
C170.145 (4)0.108 (3)0.072 (2)−0.068 (3)0.029 (3)0.000 (2)
C180.080 (2)0.133 (3)0.061 (2)−0.039 (2)0.0171 (18)−0.007 (2)
C190.0475 (14)0.0461 (13)0.0340 (13)0.0015 (10)0.0010 (10)−0.0024 (10)
C200.0494 (15)0.0553 (15)0.0323 (13)−0.0012 (11)0.0003 (11)−0.0026 (11)
C210.0447 (14)0.0539 (15)0.0383 (14)0.0022 (11)0.0022 (11)0.0031 (11)
C220.0665 (18)0.0631 (17)0.0398 (14)0.0044 (14)0.0052 (12)0.0092 (12)
C230.0493 (15)0.0513 (14)0.0355 (13)0.0007 (11)0.0009 (11)−0.0032 (11)
C240.109 (3)0.0518 (17)0.0513 (17)0.0034 (16)0.0051 (16)−0.0105 (13)
Cl10.0578 (5)0.1235 (8)0.0712 (6)−0.0265 (4)0.0062 (4)−0.0022 (5)
Cl20.0548 (5)0.1328 (8)0.0718 (6)0.0203 (5)0.0049 (4)0.0159 (5)
N10.0562 (13)0.0474 (12)0.0329 (11)−0.0004 (9)−0.0002 (9)0.0033 (9)
N20.0632 (14)0.0517 (13)0.0409 (12)−0.0004 (10)0.0007 (10)−0.0042 (10)
N30.0593 (13)0.0433 (11)0.0297 (10)−0.0032 (9)0.0010 (9)0.0015 (8)
N40.0657 (14)0.0487 (12)0.0375 (12)−0.0013 (10)0.0016 (10)0.0055 (10)
O10.0500 (11)0.0672 (12)0.0394 (10)−0.0108 (8)−0.0015 (8)0.0060 (8)
O20.0814 (14)0.0671 (12)0.0357 (10)−0.0027 (10)−0.0057 (9)0.0036 (9)
O30.0541 (11)0.0728 (12)0.0372 (10)0.0132 (9)0.0018 (8)−0.0012 (9)
O40.0762 (13)0.0562 (11)0.0345 (10)−0.0032 (9)−0.0052 (9)0.0011 (8)

Geometric parameters (Å, º)

C1—C61.378 (4)C13—Cl21.748 (3)
C1—C21.398 (4)C14—C151.393 (4)
C1—Cl11.746 (3)C14—C191.527 (3)
C2—C31.383 (4)C15—C161.383 (5)
C2—C71.527 (3)C15—H150.9300
C3—C41.393 (5)C16—C171.357 (6)
C3—H30.9300C16—H160.9300
C4—C51.375 (6)C17—C181.391 (6)
C4—H40.9300C17—H170.9300
C5—C61.369 (6)C18—H180.9300
C5—H50.9300C19—O31.399 (3)
C6—H60.9300C19—N31.477 (3)
C7—O11.400 (3)C19—C201.538 (3)
C7—N11.481 (3)C20—C211.491 (3)
C7—C81.539 (3)C20—H20A0.9700
C8—C91.484 (4)C20—H20B0.9700
C8—H8A0.9700C21—N41.281 (3)
C8—H8B0.9700C21—C221.492 (3)
C9—N21.283 (3)C22—H22A0.9600
C9—C101.492 (3)C22—H22B0.9600
C10—H10A0.9600C22—H22C0.9600
C10—H10B0.9600C23—O41.229 (3)
C10—H10C0.9600C23—N31.348 (3)
C11—O21.220 (3)C23—C241.490 (4)
C11—N11.350 (3)C24—H24A0.9600
C11—C121.503 (4)C24—H24B0.9600
C12—H12A0.9600C24—H24C0.9600
C12—H12B0.9600N1—N21.410 (3)
C12—H12C0.9600N3—N41.405 (3)
C13—C141.389 (4)O1—H10.8200
C13—C181.391 (4)O3—H3A0.8200
C6—C1—C2121.7 (3)C15—C14—C19119.3 (3)
C6—C1—Cl1116.9 (3)C16—C15—C14121.5 (4)
C2—C1—Cl1121.3 (2)C16—C15—H15119.3
C3—C2—C1117.2 (3)C14—C15—H15119.3
C3—C2—C7119.0 (2)C17—C16—C15120.2 (4)
C1—C2—C7123.4 (2)C17—C16—H16119.9
C2—C3—C4121.4 (3)C15—C16—H16119.9
C2—C3—H3119.3C16—C17—C18120.7 (3)
C4—C3—H3119.3C16—C17—H17119.6
C5—C4—C3119.5 (4)C18—C17—H17119.6
C5—C4—H4120.3C13—C18—C17118.5 (4)
C3—C4—H4120.3C13—C18—H18120.8
C6—C5—C4120.5 (3)C17—C18—H18120.8
C6—C5—H5119.7O3—C19—N3110.10 (19)
C4—C5—H5119.7O3—C19—C14112.1 (2)
C5—C6—C1119.6 (4)N3—C19—C14112.44 (19)
C5—C6—H6120.2O3—C19—C20106.78 (19)
C1—C6—H6120.2N3—C19—C20100.30 (18)
O1—C7—N1110.09 (19)C14—C19—C20114.4 (2)
O1—C7—C2112.0 (2)C21—C20—C19103.33 (19)
N1—C7—C2113.86 (19)C21—C20—H20A111.1
O1—C7—C8106.87 (19)C19—C20—H20A111.1
N1—C7—C8100.51 (18)C21—C20—H20B111.1
C2—C7—C8112.74 (19)C19—C20—H20B111.1
C9—C8—C7103.38 (19)H20A—C20—H20B109.1
C9—C8—H8A111.1N4—C21—C20114.1 (2)
C7—C8—H8A111.1N4—C21—C22121.4 (2)
C9—C8—H8B111.1C20—C21—C22124.5 (2)
C7—C8—H8B111.1C21—C22—H22A109.5
H8A—C8—H8B109.1C21—C22—H22B109.5
N2—C9—C8114.6 (2)H22A—C22—H22B109.5
N2—C9—C10122.3 (2)C21—C22—H22C109.5
C8—C9—C10123.2 (2)H22A—C22—H22C109.5
C9—C10—H10A109.5H22B—C22—H22C109.5
C9—C10—H10B109.5O4—C23—N3119.4 (2)
H10A—C10—H10B109.5O4—C23—C24122.5 (2)
C9—C10—H10C109.5N3—C23—C24118.2 (2)
H10A—C10—H10C109.5C23—C24—H24A109.5
H10B—C10—H10C109.5C23—C24—H24B109.5
O2—C11—N1120.0 (2)H24A—C24—H24B109.5
O2—C11—C12123.1 (2)C23—C24—H24C109.5
N1—C11—C12116.9 (2)H24A—C24—H24C109.5
C11—C12—H12A109.5H24B—C24—H24C109.5
C11—C12—H12B109.5C11—N1—N2122.0 (2)
H12A—C12—H12B109.5C11—N1—C7125.3 (2)
C11—C12—H12C109.5N2—N1—C7112.58 (18)
H12A—C12—H12C109.5C9—N2—N1107.4 (2)
H12B—C12—H12C109.5C23—N3—N4121.4 (2)
C14—C13—C18122.1 (3)C23—N3—C19125.1 (2)
C14—C13—Cl2121.0 (2)N4—N3—C19112.90 (18)
C18—C13—Cl2116.9 (3)C21—N4—N3107.6 (2)
C13—C14—C15117.1 (3)C7—O1—H1109.5
C13—C14—C19123.6 (2)C19—O3—H3A109.5
C6—C1—C2—C3−0.8 (4)C15—C14—C19—N3130.6 (2)
Cl1—C1—C2—C3179.10 (19)C13—C14—C19—C2061.5 (3)
C6—C1—C2—C7−174.6 (2)C15—C14—C19—C20−115.9 (3)
Cl1—C1—C2—C75.4 (3)O3—C19—C20—C21102.6 (2)
C1—C2—C3—C40.6 (4)N3—C19—C20—C21−12.3 (2)
C7—C2—C3—C4174.6 (2)C14—C19—C20—C21−132.8 (2)
C2—C3—C4—C5−0.7 (5)C19—C20—C21—N49.7 (3)
C3—C4—C5—C61.1 (5)C19—C20—C21—C22−170.9 (2)
C4—C5—C6—C1−1.4 (5)O2—C11—N1—N2176.0 (2)
C2—C1—C6—C51.2 (5)C12—C11—N1—N2−4.6 (4)
Cl1—C1—C6—C5−178.7 (3)O2—C11—N1—C70.7 (4)
C3—C2—C7—O111.4 (3)C12—C11—N1—C7−179.8 (3)
C1—C2—C7—O1−175.0 (2)O1—C7—N1—C1175.2 (3)
C3—C2—C7—N1137.2 (2)C2—C7—N1—C11−51.5 (3)
C1—C2—C7—N1−49.2 (3)C8—C7—N1—C11−172.3 (2)
C3—C2—C7—C8−109.1 (2)O1—C7—N1—N2−100.4 (2)
C1—C2—C7—C864.5 (3)C2—C7—N1—N2132.8 (2)
O1—C7—C8—C9103.5 (2)C8—C7—N1—N212.0 (2)
N1—C7—C8—C9−11.4 (2)C8—C9—N2—N1−1.1 (3)
C2—C7—C8—C9−133.0 (2)C10—C9—N2—N1179.5 (2)
C7—C8—C9—N28.5 (3)C11—N1—N2—C9176.7 (2)
C7—C8—C9—C10−172.0 (2)C7—N1—N2—C9−7.5 (3)
C18—C13—C14—C150.0 (4)O4—C23—N3—N4173.4 (2)
Cl2—C13—C14—C15−179.9 (2)C24—C23—N3—N4−7.5 (4)
C18—C13—C14—C19−177.4 (3)O4—C23—N3—C192.1 (4)
Cl2—C13—C14—C192.7 (3)C24—C23—N3—C19−178.8 (2)
C13—C14—C15—C161.0 (4)O3—C19—N3—C2372.1 (3)
C19—C14—C15—C16178.6 (3)C14—C19—N3—C23−53.7 (3)
C14—C15—C16—C17−1.4 (5)C20—C19—N3—C23−175.6 (2)
C15—C16—C17—C180.8 (6)O3—C19—N3—N4−99.7 (2)
C14—C13—C18—C17−0.7 (5)C14—C19—N3—N4134.4 (2)
Cl2—C13—C18—C17179.2 (3)C20—C19—N3—N412.5 (3)
C16—C17—C18—C130.3 (6)C20—C21—N4—N3−1.9 (3)
C13—C14—C19—O3−176.7 (2)C22—C21—N4—N3178.6 (2)
C15—C14—C19—O35.9 (3)C23—N3—N4—C21−179.6 (2)
C13—C14—C19—N3−52.0 (3)C19—N3—N4—C21−7.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···AD—HH···AD···AD—H···A
O1—–H1···..O4i0.821.972.748 (3)159
O3—–H3A···..O2ii0.822.032.792 (3)155
C8—–H8B···..O3iii0.972.533.410 (3)151
C20—–H20B···..O1iv0.972.503.354 (3)147

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2378).

References

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