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

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ISSN: 2056-9890

4-Cyano-N-ethyl­spiro­[chromene-2,4′-piperidine]-1′-carboxamide

aDepartment of Physics, Thiagarajar College, Madurai 625 009, India
*Correspondence e-mail: vasan692000@yahoo.co.in

(Received 10 November 2012; accepted 18 December 2012; online 22 December 2012)

The title compound, C17H19N3O2, crystallizes with two independent mol­ecules (A and B) in the asymmetric unit. In both mol­ecules, the pyran ring has a twisted conformation (5S4), with Q = 0.301 (3) Å, θ = 116.7 (6) and φ= 213.6 (7)° for mol­ecule A, and Q = 0.364 (2) Å, θ = 113.7 (3) and φ = 213.0 (4)° for mol­ecule B. In mol­ecule B, the terminal ethyl group is disordered over two orientations with an occupancy ratio of 0.55 (1):0.45 (1). In the crystal, mol­ecules A and B form very similar but separate R12(7) motifs through N—H⋯O and C—H⋯O hydrogen bonds. The resulting chains along [001] are inter­linked by weaker C—H⋯O and C—H⋯π inter­actions, forming layers parallel to the bc plane.

Related literature

For related structures, see: Rajalakshmi et al. (2012[Rajalakshmi, P., Srinivasan, N. & Krishnakumar, R. V. (2012). Acta Cryst. E68, o2732.]). For their biological activity, see: Kemnitzer et al. (2004[Kemnitzer, W., Drewe, J., Jiang, S., Zhang, H., Wang, Y. & Zhao, J. (2004). J. Med. Chem. 47, 6299-6310.]); Mahdavi et al. (2011[Mahdavi, M., Davoodi, J., Zali, M. R. & Foroumadi, A. (2011). Biomed. Pharm. 65, 175-182.]); Patil et al. (2012[Patil, D. U., Nikum, P. A., Nagle, S. P. & Mahulikar, P. P. (2012). J. Pharm. Res. 5, 1383-1386.]); Vosooghi et al. (2010[Vosooghi, M., Rajabalian, S., Sorkhi, M., Badinloo, M., Nakhjiri, M., Negahbani, A. S., Asadipour, A., Mahdavi, M., Shafiee, A. & Foroumadi, A. (2010). J. Res. Pharm. Sci. 5, 9-14.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C17H19N3O2

  • Mr = 297.35

  • Monoclinic, P 21 /c

  • a = 22.7845 (8) Å

  • b = 14.3370 (5) Å

  • c = 9.8442 (3) Å

  • β = 90.783 (1)°

  • V = 3215.42 (19) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 298 K

  • 0.35 × 0.30 × 0.25 mm

Data collection
  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) Tmin = 0.972, Tmax = 0.980

  • 26353 measured reflections

  • 5377 independent reflections

  • 3664 reflections with I > 2σ(I)

  • Rint = 0.028

Refinement
  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 0.177

  • S = 1.04

  • 5377 reflections

  • 455 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.20 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C4B–C9B benzene ring

D—H⋯A D—H H⋯A DA D—H⋯A
N3A—H1N3⋯O2Ai 0.81 (3) 2.12 (3) 2.915 (3) 170 (3)
N3B—H2N3⋯O2Bii 0.83 (2) 2.19 (3) 2.983 (3) 160 (2)
C11A—H11B⋯O2Ai 1.00 (3) 2.27 (3) 3.246 (3) 165 (2)
C11B—H11C⋯O2Bii 0.95 (3) 2.50 (3) 3.344 (3) 147 (2)
C9B—H9B⋯O2Biii 0.92 (3) 2.58 (3) 3.473 (3) 163 (2)
C13A—H13BCg1iv 0.97 2.91 3.843 (3) 163
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iii) -x+2, -y+1, -z+2; (iv) [x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison Wisconsin, USA.]); data reduction: SAINT; 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: PLUTON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Chromene with piperidine derivatives are potent agents inducing apoptosis (Kemnitzer et al., 2004). They also exhibit cytotoxic (Vosooghi et al., 2010), antifungal (Mahdavi et al., 2011) and antimycobacterial activities (Patil et al., 2012). In a continuation to our study of the structural features of 1'-benzyl spiro[chromene-2,4'-piperidine]-4-carbonitrile (Rajalakshmi et al., 2012), we report here the crystal structure of the title compound: 4-cyano-N-ethylspiro[chromene-2,4'-piperidine]- 1'-carboxamide.

The title compound contains two molecules in the asymmetric unit (Fig. 1). The piperidine ring forms dihedral angles of 11.9 (2)° and 78.2 (1)° for molecule A, 7.9 (8)° and 74.3 (1)° for molecule B, with the N-ethyl carboxamide group and chroman ring, respectively. The pyran ring in the molecules A and B (C8/C7/C2/O1/C1/C9) adopts a twisted conformation (5S4) with O1 and C1 atoms deviating respectively from the mean plane defined by the rest of the atoms by -0.1926 (5) Å and 0.2626 (5) Å in molecule A, and by -0.2375 (4) Å and 0.3063 (5) Å in molecule B. The piperidine ring (C1/C10/C11/N2/C12/C13) adopts a chair conformation (1C4) with C1 and N2 atoms deviating respectively from the rest of the atoms by -0.6644 (3) Å and 0.6065 (3) Å in molecule A and by -0.6418 (4) Å and 0.6263 (4)Å in molecule B (Cremer & Pople, 1975). In molecule B, the terminal ethyl group is disordered over two positions with refined occupancy ratios of 0.55 (1):0.45 (1).

Molecules A and B form separate chains along [001] through similar R21(7) motifs (Bernstein et al., 1995) through N—H···O and C—H···O hydrogen bonds. The chains made of molecules B form layers parallel to bc plane owing to formation of an additional C9B—H9B···O2B hydrogen bond. The crystal structure also has a noteworthy C—H···π interaction that appears to be a weaker link between molecules A and B resulting in layers parallel to the (100) plane (Fig.2 and Fig.3).

Related literature top

For related structures, see: Rajalakshmi et al. (2012). For their biological activity, see: Kemnitzer et al. (2004); Mahdavi et al. (2011); Patil et al. (2012); Vosooghi et al. (2010). For puckering parameters, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

Trimethylsilylcyanide (1.2 mmol) was added to a mixture of N-ethyl-4-oxospiro[chroman-2,4'-piperidine]-1'-carboxamide (1.0 mmol) and catalytic amount of ZnI2 in dichloromethane (10 vol) under a nitrogen atmosphere. The reaction mixture was stirred at 50°C for 6 h and then cooled down to the room temperature; then diluted HCl (5 ml) was added and stirring continued for additional 2 h. The solution was extracted with ethylacetate (20 ml), dried over Na2SO4 and evaporated to dryness. The crude product was dissolved in benzene (10 ml), to which tosic acid (0.1 mmol) had been added, and the solution was heated to reflux for 2 h. After completion of the reaction as indicated by TLC, the reaction mixture was concentrated under reduced pressure. The residue was diluted with ethylacetate (20 ml), washed with bicarbonate solution (10 ml) dried and concentrated. The crude product was purified by column chromatography to provide the desired product as colorless solid. Crystals of the title compound were grown from its solution in ethanol by slow evaporation at room temperature.

Refinement top

The positions of the hydrogen atoms bound to N3A, C11A, C13A, N3B, C9B and C11B were allowed to refine with isotropic temperature factors since they participate in the hydrogen-bonding. All other hydrogen atoms were included into the model at geometrically calculated positions (C—H target distance 0.96 Å for methyl hydrogen atoms, 0.93 Å for all others) and refined using a riding model with their Uiso constrained to 1.2 times Ueq (1.5 times for methyl H atoms) of the respective atom to which the hydrogen atom binds. The methyl H atoms involving the C16 atom of molecules A and B were allowed to refine with their torsion angles optimized. In molecule B, the terminal ethyl group C15B and C16B is disordered over two sets of sites the treatment of which converged with occupancy values of 0.55 (1) and 0.45 (1) for the major and minor components, respectively.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLUTON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecules of the title compound with atom-labeling scheme. Displacement ellipsoids are drawn at 30% probability. For the sake of clarity, H atoms are not shown.
[Figure 2] Fig. 2. Packing diagram of the title compound, showing formation of the separate R21 (7) motifs by molecules A and B (molecules A are shown in red, molecules B - in black). The cyano and ethyl groups were omitted for clarity as well as the H atoms not involved in the hydrogen bonding.
[Figure 3] Fig. 3. The layers formed by molecules B along (100) plane. Non-essential groups and most hydrogen atoms were omitted for clarity.
4-Cyano-N-ethylspiro[chromene-2,4'-piperidine]-1'-carboxamide top
Crystal data top
C17H19N3O2F(000) = 1264
Mr = 297.35Dx = 1.228 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5377 reflections
a = 22.7845 (8) Åθ = 2–24.5°
b = 14.3370 (5) ŵ = 0.08 mm1
c = 9.8442 (3) ÅT = 298 K
β = 90.783 (1)°Block, colourless
V = 3215.42 (19) Å30.35 × 0.30 × 0.25 mm
Z = 8
Data collection top
Bruker Kappa APEXII
diffractometer
5377 independent reflections
Radiation source: fine-focus sealed tube3664 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
ϕ and ω scansθmax = 24.5°, θmin = 1.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2008)
h = 2626
Tmin = 0.972, Tmax = 0.980k = 1616
26353 measured reflectionsl = 1111
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.177H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0985P)2 + 0.7688P]
where P = (Fo2 + 2Fc2)/3
5377 reflections(Δ/σ)max < 0.001
455 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.20 e Å3
Crystal data top
C17H19N3O2V = 3215.42 (19) Å3
Mr = 297.35Z = 8
Monoclinic, P21/cMo Kα radiation
a = 22.7845 (8) ŵ = 0.08 mm1
b = 14.3370 (5) ÅT = 298 K
c = 9.8442 (3) Å0.35 × 0.30 × 0.25 mm
β = 90.783 (1)°
Data collection top
Bruker Kappa APEXII
diffractometer
5377 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2008)
3664 reflections with I > 2σ(I)
Tmin = 0.972, Tmax = 0.980Rint = 0.028
26353 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.177H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.29 e Å3
5377 reflectionsΔρmin = 0.20 e Å3
455 parameters
Special details top

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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

21.7749 (0.0093) x - 3.7501 (0.0221) y + 1.2007 (0.0105) z = 19.0074 (0.0242)

* 0.0040 (0.0012) C10B * -0.0040 (0.0012) C11B * 0.0040 (0.0012) C12B * -0.0040 (0.0012) C13B 0.6065 (0.0031) N2B -0.6644 (0.0031) C1B

Rms deviation of fitted atoms = 0.0040

- 7.4187 (0.0441) x + 12.7666 (0.0128) y + 3.1729 (0.0124) z = 1.9928 (0.0318)

Angle to previous plane (with approximate esd) = 59.92 ( 0.15 )

* -0.0108 (0.0016) C10A * 0.0109 (0.0016) C11A * -0.0109 (0.0016) C12A * 0.0108 (0.0016) C13A -0.6263 (0.0038) N2A 0.6418 (0.0039) C1A

Rms deviation of fitted atoms = 0.0109

4.5322 (0.0409) x - 8.3873 (0.0214) y + 7.7125 (0.0087) z = 2.7977 (0.0417)

Angle to previous plane (with approximate esd) = 70.38 ( 0.11 )

* 0.0378 (0.0016) C7A * 0.0217 (0.0009) C9A * -0.0402 (0.0017) C8A * -0.0193 (0.0008) C2A 0.2626 (0.0051) C1A -0.1926 (0.0048) O1A

Rms deviation of fitted atoms = 0.0312

5.5265 (0.0340) x - 2.7276 (0.0239) y + 9.3313 (0.0033) z = 11.8513 (0.0329)

Angle to previous plane (with approximate esd) = 24.84 ( 0.15 )

* 0.0573 (0.0014) C7B * 0.0322 (0.0008) C9B * -0.0600 (0.0015) C8B * -0.0295 (0.0007) C2B 0.3063 (0.0047) C1B -0.2375 (0.0041) O1B

Rms deviation of fitted atoms = 0.0469

13.1321 (0.0221) x - 10.5040 (0.0116) y - 3.6406 (0.0129) z = 2.2898 (0.0197)

Angle to previous plane (with approximate esd) = 86.26 ( 0.11 )

* 0.2282 (0.0021) C10A * -0.2326 (0.0021) C11A * -0.2132 (0.0023) C12A * 0.2074 (0.0023) C13A * 0.2229 (0.0020) N2A * -0.2128 (0.0019) C1A

Rms deviation of fitted atoms = 0.2197

16.1311 (0.0326) x - 9.6533 (0.0246) y - 2.1927 (0.0143) z = 5.2730 (0.0209)

Angle to previous plane (with approximate esd) = 11.90 ( 0.24 )

* 0.0010 (0.0008) O2A * -0.0020 (0.0016) C14A * 0.0019 (0.0015) N3A * -0.0009 (0.0007) C15A

Rms deviation of fitted atoms = 0.0015

13.1321 (0.0221) x - 10.5040 (0.0116) y - 3.6406 (0.0129) z = 2.2898 (0.0197)

Angle to previous plane (with approximate esd) = 11.90 ( 0.24 )

* 0.2282 (0.0021) C10A * -0.2326 (0.0021) C11A * -0.2132 (0.0023) C12A * 0.2074 (0.0023) C13A * 0.2229 (0.0020) N2A * -0.2128 (0.0019) C1A

Rms deviation of fitted atoms = 0.2197

4.0940 (0.0233) x - 7.7943 (0.0130) y + 8.0459 (0.0062) z = 3.0223 (0.0189)

Angle to previous plane (with approximate esd) = 78.16 ( 0.09 )

* -0.0636 (0.0019) C9A * 0.1923 (0.0017) C1A * -0.0711 (0.0019) C8A * 0.0861 (0.0018) C7A * 0.0441 (0.0018) C2A * -0.1878 (0.0017) O1A

Rms deviation of fitted atoms = 0.1229

19.4554 (0.0116) x - 7.4511 (0.0119) y + 0.1595 (0.0105) z = 13.7691 (0.0188)

Angle to previous plane (with approximate esd) = 62.69 ( 0.09 )

* 0.2327 (0.0017) C10B * -0.2207 (0.0017) C11B * -0.2127 (0.0017) C12B * 0.2240 (0.0017) C13B * 0.2129 (0.0017) N2B * -0.2363 (0.0016) C1B

Rms deviation of fitted atoms = 0.2234

19.0116 (0.1135) x - 7.7504 (0.1004) y - 1.1689 (0.0356) z = 12.1762 (0.2227)

Angle to previous plane (with approximate esd) = 7.92 ( 0.76 )

* 0.0316 (0.0019) O2B * -0.0581 (0.0036) C14B * 0.0512 (0.0032) N3B * -0.0247 (0.0015) C15B_a

Rms deviation of fitted atoms = 0.0436

19.4554 (0.0116) x - 7.4511 (0.0119) y + 0.1595 (0.0105) z = 13.7691 (0.0188)

Angle to previous plane (with approximate esd) = 7.92 ( 0.76 )

* 0.2327 (0.0017) C10B * -0.2207 (0.0017) C11B * -0.2127 (0.0017) C12B * 0.2240 (0.0017) C13B * 0.2129 (0.0017) N2B * -0.2363 (0.0016) C1B

Rms deviation of fitted atoms = 0.2234

4.1399 (0.0218) x - 2.4193 (0.0136) y + 9.5114 (0.0026) z = 11.0331 (0.0176)

Angle to previous plane (with approximate esd) = 74.34 ( 0.08 )

* -0.0681 (0.0018) C9B * 0.2285 (0.0016) C1B * -0.0966 (0.0017) C8B * 0.1149 (0.0015) C7B * 0.0475 (0.0015) C2B * -0.2262 (0.0014) O1B

Rms deviation of fitted atoms = 0.1488

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*/UeqOcc. (<1)
O1A0.64156 (8)0.54792 (13)0.5566 (2)0.0827 (6)
O2A0.54458 (9)0.21606 (13)0.64983 (17)0.0765 (5)
N1A0.86504 (18)0.6414 (3)0.5007 (5)0.1602 (17)
N2A0.59436 (10)0.32206 (14)0.52456 (19)0.0636 (6)
N3A0.52207 (10)0.22847 (16)0.4292 (2)0.0679 (6)
C1A0.67909 (12)0.47355 (17)0.5127 (3)0.0631 (7)
C2A0.66403 (15)0.61628 (18)0.6402 (3)0.0770 (8)
C3A0.62636 (19)0.6657 (2)0.7180 (3)0.1049 (11)
H3A0.58680.64980.72080.126*
C4A0.6473 (3)0.7387 (3)0.7913 (4)0.1313 (18)
C5A0.7030 (4)0.7632 (3)0.7908 (5)0.150 (2)
H5A0.71550.81430.84180.179*
C6A0.7447 (2)0.7118 (2)0.7122 (4)0.1209 (16)
H6A0.78430.72790.71300.145*
C7A0.72431 (15)0.63792 (17)0.6358 (3)0.0767 (9)
C8A0.75991 (13)0.5822 (2)0.5441 (3)0.0773 (8)
C9A0.73837 (15)0.5081 (2)0.4842 (3)0.0775 (8)
C10A0.64728 (14)0.43474 (18)0.3889 (3)0.0733 (8)
H10A0.64230.48420.32250.088*
H10B0.67140.38660.34850.088*
C11A0.58882 (14)0.3948 (2)0.4199 (3)0.0722 (8)
C12A0.62276 (14)0.3556 (2)0.6501 (3)0.0826 (9)
H12A0.62780.30390.71270.099*
H12B0.59780.40150.69270.099*
C13A0.68102 (13)0.3981 (2)0.6220 (3)0.0744 (8)
H13A0.70770.34930.59390.089*
H13B0.69660.42500.70540.089*
C14A0.55232 (11)0.25439 (16)0.5395 (2)0.0550 (6)
C15A0.47839 (14)0.1548 (2)0.4335 (3)0.0863 (9)
H15A0.47970.12620.52280.104*
H15B0.43980.18230.42100.104*
C16A0.48610 (19)0.0829 (3)0.3323 (5)0.1428 (18)
H16A0.48250.10980.24330.214*
H16B0.45660.03580.34320.214*
H16C0.52430.05540.34330.214*
C17A0.81935 (18)0.6132 (3)0.5193 (4)0.1113 (13)
O1B0.82241 (6)0.54557 (10)0.91701 (17)0.0585 (4)
O2B1.00094 (7)0.69692 (11)1.21492 (17)0.0658 (5)
N1B0.78919 (13)0.18872 (18)0.8024 (3)0.1075 (10)
N2B0.95277 (8)0.63343 (12)1.03499 (18)0.0512 (5)
N3B1.01500 (10)0.75979 (14)1.0100 (3)0.0654 (6)
C1B0.87563 (9)0.48999 (15)0.9275 (2)0.0506 (6)
C2B0.77116 (9)0.50472 (16)0.9577 (2)0.0509 (6)
C3B0.72738 (11)0.56214 (19)1.0024 (3)0.0669 (7)
H3B0.73370.62601.01060.080*
C4B0.67375 (12)0.5239 (2)1.0350 (3)0.0795 (8)
H4B0.64380.56261.06450.095*
C5B0.66405 (12)0.4301 (2)1.0248 (3)0.0782 (8)
H5B0.62790.40521.04820.094*
C6B0.70809 (11)0.37264 (19)0.9795 (2)0.0649 (7)
H6B0.70150.30880.97230.078*
C7B0.76231 (9)0.40935 (16)0.9444 (2)0.0523 (6)
C8B0.81077 (10)0.35561 (16)0.8874 (3)0.0594 (6)
C9B0.86373 (11)0.39305 (17)0.8769 (3)0.0617 (7)
C10B0.91981 (10)0.54055 (15)0.8409 (2)0.0536 (6)
H10C0.90460.54510.74860.064*
H10D0.95590.50460.83870.064*
C11B0.93324 (12)0.63759 (17)0.8938 (2)0.0545 (6)
C12B0.91192 (11)0.58582 (17)1.1254 (2)0.0606 (6)
H12C0.87600.62181.13150.073*
H12D0.92920.58151.21570.073*
C13B0.89774 (10)0.48906 (16)1.0738 (2)0.0583 (6)
H13C0.86810.46141.13090.070*
H13D0.93270.45061.08020.070*
C14B0.98940 (9)0.69875 (14)1.0919 (2)0.0485 (5)
C15B1.0460 (8)0.8346 (14)1.0830 (13)0.070 (3)0.550 (10)
H15C1.06810.80971.15970.083*0.550 (10)
H15D1.01850.88081.11580.083*0.550 (10)
C16B1.0868 (4)0.8769 (6)0.9786 (7)0.116 (4)0.550 (10)
H16D1.06410.90030.90310.175*0.550 (10)
H16E1.11350.83000.94730.175*0.550 (10)
H16F1.10860.92711.01950.175*0.550 (10)
C15C1.0598 (9)0.8312 (15)1.0386 (15)0.066 (4)0.450 (10)
H15E1.07750.82031.12740.079*0.450 (10)
H15F1.09050.82790.97130.079*0.450 (10)
C16C1.0324 (5)0.9228 (5)1.0349 (9)0.106 (4)0.450 (10)
H16G1.06080.96941.06010.159*0.450 (10)
H16H1.00050.92431.09750.159*0.450 (10)
H16I1.01790.93530.94480.159*0.450 (10)
C17B0.79915 (12)0.2625 (2)0.8393 (3)0.0758 (8)
H9A0.7620 (14)0.477 (2)0.420 (4)0.101 (11)*
H1N30.5307 (12)0.2494 (18)0.356 (3)0.066 (8)*
H4A0.6205 (17)0.779 (3)0.852 (4)0.133 (13)*
H11A0.5669 (13)0.455 (2)0.456 (3)0.093 (9)*
H11B0.5679 (12)0.3651 (18)0.341 (3)0.081 (8)*
H2N31.0026 (10)0.7676 (16)0.932 (3)0.052 (7)*
H9B0.8947 (12)0.3614 (18)0.840 (3)0.072 (8)*
H11C0.9634 (12)0.6634 (17)0.839 (3)0.069 (7)*
H11D0.8987 (11)0.6814 (17)0.889 (2)0.061 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0796 (13)0.0716 (12)0.0965 (15)0.0050 (9)0.0153 (10)0.0284 (10)
O2A0.1061 (15)0.0809 (12)0.0426 (10)0.0100 (10)0.0012 (9)0.0106 (8)
N1A0.112 (3)0.164 (4)0.204 (4)0.044 (3)0.022 (3)0.075 (3)
N2A0.0885 (15)0.0635 (12)0.0384 (10)0.0106 (11)0.0159 (10)0.0057 (9)
N3A0.0779 (15)0.0810 (15)0.0448 (13)0.0190 (12)0.0040 (11)0.0060 (11)
C1A0.0778 (17)0.0551 (14)0.0563 (15)0.0037 (12)0.0063 (13)0.0072 (11)
C2A0.118 (3)0.0527 (15)0.0595 (16)0.0125 (16)0.0162 (16)0.0056 (12)
C3A0.152 (3)0.076 (2)0.087 (2)0.030 (2)0.013 (2)0.0171 (18)
C4A0.235 (6)0.072 (3)0.086 (3)0.027 (3)0.034 (3)0.025 (2)
C5A0.295 (8)0.065 (2)0.087 (3)0.026 (4)0.059 (4)0.017 (2)
C6A0.205 (4)0.071 (2)0.086 (2)0.043 (3)0.057 (3)0.0088 (19)
C7A0.120 (3)0.0477 (15)0.0611 (17)0.0121 (15)0.0343 (17)0.0111 (12)
C8A0.091 (2)0.0588 (16)0.081 (2)0.0131 (15)0.0197 (16)0.0239 (15)
C9A0.092 (2)0.0634 (18)0.077 (2)0.0001 (16)0.0027 (17)0.0111 (15)
C10A0.112 (2)0.0593 (15)0.0487 (15)0.0092 (15)0.0067 (14)0.0058 (11)
C11A0.107 (2)0.0584 (16)0.0508 (15)0.0139 (16)0.0289 (15)0.0066 (12)
C12A0.099 (2)0.104 (2)0.0443 (14)0.0282 (17)0.0189 (14)0.0074 (14)
C13A0.0867 (19)0.0840 (18)0.0522 (15)0.0136 (15)0.0161 (13)0.0115 (13)
C14A0.0685 (15)0.0546 (13)0.0419 (13)0.0066 (11)0.0011 (11)0.0011 (10)
C15A0.083 (2)0.103 (2)0.0737 (19)0.0332 (17)0.0007 (15)0.0026 (17)
C16A0.120 (3)0.124 (3)0.186 (5)0.062 (3)0.051 (3)0.057 (3)
C17A0.102 (3)0.103 (3)0.128 (3)0.022 (2)0.021 (2)0.048 (2)
O1B0.0451 (9)0.0468 (9)0.0835 (12)0.0008 (7)0.0023 (8)0.0072 (8)
O2B0.0766 (12)0.0687 (11)0.0517 (11)0.0012 (8)0.0092 (8)0.0092 (8)
N1B0.109 (2)0.0665 (17)0.146 (3)0.0219 (15)0.0115 (18)0.0188 (16)
N2B0.0563 (11)0.0536 (11)0.0437 (10)0.0097 (8)0.0004 (9)0.0001 (8)
N3B0.0703 (14)0.0572 (13)0.0681 (15)0.0167 (10)0.0219 (12)0.0083 (11)
C1B0.0402 (11)0.0490 (12)0.0626 (15)0.0002 (9)0.0025 (10)0.0007 (10)
C2B0.0428 (12)0.0586 (14)0.0512 (13)0.0002 (10)0.0053 (10)0.0092 (10)
C3B0.0570 (15)0.0717 (16)0.0721 (17)0.0086 (12)0.0044 (13)0.0073 (13)
C4B0.0570 (17)0.103 (2)0.079 (2)0.0101 (15)0.0143 (14)0.0103 (17)
C5B0.0547 (16)0.110 (2)0.0702 (18)0.0109 (16)0.0091 (14)0.0177 (16)
C6B0.0627 (16)0.0757 (17)0.0560 (15)0.0176 (13)0.0053 (12)0.0149 (12)
C7B0.0498 (13)0.0591 (14)0.0476 (13)0.0053 (11)0.0102 (10)0.0085 (10)
C8B0.0592 (15)0.0477 (13)0.0709 (16)0.0048 (11)0.0127 (12)0.0031 (11)
C9B0.0483 (14)0.0514 (14)0.0853 (19)0.0042 (11)0.0031 (13)0.0038 (12)
C10B0.0497 (13)0.0592 (14)0.0517 (13)0.0053 (10)0.0033 (10)0.0056 (10)
C11B0.0581 (15)0.0580 (15)0.0473 (14)0.0105 (12)0.0012 (12)0.0026 (10)
C12B0.0589 (14)0.0733 (16)0.0498 (14)0.0075 (12)0.0068 (11)0.0032 (11)
C13B0.0517 (13)0.0593 (14)0.0640 (16)0.0062 (11)0.0015 (11)0.0127 (11)
C14B0.0501 (12)0.0438 (12)0.0517 (14)0.0066 (10)0.0043 (10)0.0042 (10)
C15B0.075 (8)0.071 (4)0.063 (7)0.024 (5)0.001 (5)0.005 (6)
C16B0.129 (7)0.128 (6)0.092 (5)0.075 (6)0.017 (5)0.023 (4)
C15C0.069 (9)0.070 (6)0.058 (9)0.028 (6)0.003 (6)0.011 (7)
C16C0.142 (9)0.063 (5)0.114 (7)0.022 (5)0.008 (6)0.008 (4)
C17B0.0683 (17)0.0597 (17)0.099 (2)0.0108 (13)0.0089 (15)0.0035 (15)
Geometric parameters (Å, º) top
O1A—C2A1.374 (3)N2B—C14B1.369 (3)
O1A—C1A1.437 (3)N2B—C11B1.455 (3)
O2A—C14A1.232 (3)N2B—C12B1.465 (3)
N1A—C17A1.134 (4)N3B—C14B1.330 (3)
N2A—C14A1.373 (3)N3B—C15B1.466 (19)
N2A—C12A1.468 (3)N3B—C15C1.47 (2)
N2A—C11A1.470 (3)N3B—H2N30.83 (2)
N3A—C14A1.331 (3)C1B—C9B1.500 (3)
N3A—C15A1.452 (4)C1B—C10B1.513 (3)
N3A—H1N30.81 (3)C1B—C13B1.519 (3)
C1A—C9A1.469 (4)C2B—C3B1.371 (3)
C1A—C10A1.516 (3)C2B—C7B1.388 (3)
C1A—C13A1.526 (4)C3B—C4B1.381 (4)
C2A—C3A1.358 (4)C3B—H3B0.9300
C2A—C7A1.409 (4)C4B—C5B1.365 (4)
C3A—C4A1.354 (6)C4B—H4B0.9300
C3A—H3A0.9300C5B—C6B1.378 (4)
C4A—C5A1.318 (8)C5B—H5B0.9300
C4A—H4A1.03 (4)C6B—C7B1.391 (3)
C5A—C6A1.437 (8)C6B—H6B0.9300
C5A—H5A0.9300C7B—C8B1.464 (3)
C6A—C7A1.377 (4)C8B—C9B1.326 (3)
C6A—H6A0.9300C8B—C17B1.440 (4)
C7A—C8A1.459 (4)C9B—H9B0.92 (3)
C8A—C9A1.307 (4)C10B—C11B1.515 (3)
C8A—C17A1.449 (5)C10B—H10C0.9700
C9A—H9A0.94 (3)C10B—H10D0.9700
C10A—C11A1.486 (4)C11B—H11C0.95 (3)
C10A—H10A0.9700C11B—H11D1.01 (2)
C10A—H10B0.9700C12B—C13B1.511 (3)
C11A—H11A1.06 (3)C12B—H12C0.9700
C11A—H11B1.00 (3)C12B—H12D0.9700
C12A—C13A1.490 (4)C13B—H13C0.9700
C12A—H12A0.9700C13B—H13D0.9700
C12A—H12B0.9700C15B—C16B1.522 (14)
C13A—H13A0.9700C15B—H15C0.9700
C13A—H13B0.9700C15B—H15D0.9700
C15A—C16A1.446 (5)C16B—H16D0.9600
C15A—H15A0.9700C16B—H16E0.9600
C15A—H15B0.9700C16B—H16F0.9600
C16A—H16A0.9600C15C—C16C1.46 (2)
C16A—H16B0.9600C15C—H15E0.9700
C16A—H16C0.9600C15C—H15F0.9700
O1B—C2B1.371 (3)C16C—H16G0.9600
O1B—C1B1.454 (2)C16C—H16H0.9600
O2B—C14B1.236 (3)C16C—H16I0.9600
N1B—C17B1.140 (3)
C2A—O1A—C1A119.4 (2)C14B—N3B—C15B113.3 (5)
C14A—N2A—C12A116.2 (2)C14B—N3B—C15C130.6 (6)
C14A—N2A—C11A121.5 (2)C14B—N3B—H2N3120.6 (16)
C12A—N2A—C11A113.0 (2)C15B—N3B—H2N3121.0 (17)
C14A—N3A—C15A121.8 (2)C15C—N3B—H2N3108.1 (18)
C14A—N3A—H1N3120 (2)O1B—C1B—C9B109.72 (17)
C15A—N3A—H1N3118.2 (19)O1B—C1B—C10B104.95 (17)
O1A—C1A—C9A111.1 (2)C9B—C1B—C10B112.0 (2)
O1A—C1A—C10A103.6 (2)O1B—C1B—C13B109.74 (18)
C9A—C1A—C10A113.6 (2)C9B—C1B—C13B111.29 (19)
O1A—C1A—C13A109.0 (2)C10B—C1B—C13B108.90 (17)
C9A—C1A—C13A110.8 (2)C3B—C2B—O1B117.6 (2)
C10A—C1A—C13A108.4 (2)C3B—C2B—C7B121.1 (2)
C3A—C2A—O1A118.5 (3)O1B—C2B—C7B121.1 (2)
C3A—C2A—C7A121.8 (3)C2B—C3B—C4B119.1 (3)
O1A—C2A—C7A119.6 (3)C2B—C3B—H3B120.5
C4A—C3A—C2A118.9 (5)C4B—C3B—H3B120.5
C4A—C3A—H3A120.6C5B—C4B—C3B121.1 (3)
C2A—C3A—H3A120.6C5B—C4B—H4B119.5
C5A—C4A—C3A122.5 (5)C3B—C4B—H4B119.5
C5A—C4A—H4A116 (2)C4B—C5B—C6B119.7 (3)
C3A—C4A—H4A122 (3)C4B—C5B—H5B120.2
C4A—C5A—C6A120.6 (4)C6B—C5B—H5B120.2
C4A—C5A—H5A119.7C5B—C6B—C7B120.5 (3)
C6A—C5A—H5A119.7C5B—C6B—H6B119.8
C7A—C6A—C5A117.9 (4)C7B—C6B—H6B119.8
C7A—C6A—H6A121.0C2B—C7B—C6B118.5 (2)
C5A—C6A—H6A121.0C2B—C7B—C8B116.42 (19)
C6A—C7A—C2A118.3 (4)C6B—C7B—C8B125.0 (2)
C6A—C7A—C8A124.9 (4)C9B—C8B—C17B120.9 (2)
C2A—C7A—C8A116.7 (2)C9B—C8B—C7B120.6 (2)
C9A—C8A—C17A121.3 (4)C17B—C8B—C7B118.5 (2)
C9A—C8A—C7A121.0 (3)C8B—C9B—C1B120.6 (2)
C17A—C8A—C7A117.7 (3)C8B—C9B—H9B122.4 (16)
C8A—C9A—C1A121.9 (3)C1B—C9B—H9B117.0 (16)
C8A—C9A—H9A118 (2)C1B—C10B—C11B112.3 (2)
C1A—C9A—H9A120 (2)C1B—C10B—H10C109.1
C11A—C10A—C1A113.4 (2)C11B—C10B—H10C109.1
C11A—C10A—H10A108.9C1B—C10B—H10D109.1
C1A—C10A—H10A108.9C11B—C10B—H10D109.1
C11A—C10A—H10B108.9H10C—C10B—H10D107.9
C1A—C10A—H10B108.9N2B—C11B—C10B110.37 (19)
H10A—C10A—H10B107.7N2B—C11B—H11C110.2 (15)
N2A—C11A—C10A110.4 (2)C10B—C11B—H11C107.7 (15)
N2A—C11A—H11A112.2 (16)N2B—C11B—H11D107.3 (13)
C10A—C11A—H11A100.4 (16)C10B—C11B—H11D113.7 (13)
N2A—C11A—H11B106.1 (15)H11C—C11B—H11D107 (2)
C10A—C11A—H11B115.1 (15)N2B—C12B—C13B110.99 (19)
H11A—C11A—H11B113 (2)N2B—C12B—H12C109.4
N2A—C12A—C13A111.2 (2)C13B—C12B—H12C109.4
N2A—C12A—H12A109.4N2B—C12B—H12D109.4
C13A—C12A—H12A109.4C13B—C12B—H12D109.4
N2A—C12A—H12B109.4H12C—C12B—H12D108.0
C13A—C12A—H12B109.4C12B—C13B—C1B112.18 (19)
H12A—C12A—H12B108.0C12B—C13B—H13C109.2
C12A—C13A—C1A113.8 (2)C1B—C13B—H13C109.2
C12A—C13A—H13A108.8C12B—C13B—H13D109.2
C1A—C13A—H13A108.8C1B—C13B—H13D109.2
C12A—C13A—H13B108.8H13C—C13B—H13D107.9
C1A—C13A—H13B108.8O2B—C14B—N3B121.2 (2)
H13A—C13A—H13B107.7O2B—C14B—N2B120.5 (2)
O2A—C14A—N3A121.0 (2)N3B—C14B—N2B118.1 (2)
O2A—C14A—N2A121.2 (2)N3B—C15B—C16B104.8 (8)
N3A—C14A—N2A117.7 (2)N3B—C15B—H15C110.8
C16A—C15A—N3A114.1 (3)C16B—C15B—H15C110.8
C16A—C15A—H15A108.7N3B—C15B—H15D110.8
N3A—C15A—H15A108.7C16B—C15B—H15D110.8
C16A—C15A—H15B108.7H15C—C15B—H15D108.9
N3A—C15A—H15B108.7C16C—C15C—N3B109.1 (14)
H15A—C15A—H15B107.6C16C—C15C—H15E109.9
C15A—C16A—H16A109.5N3B—C15C—H15E109.9
C15A—C16A—H16B109.5C16C—C15C—H15F109.9
H16A—C16A—H16B109.5N3B—C15C—H15F109.9
C15A—C16A—H16C109.5H15E—C15C—H15F108.3
H16A—C16A—H16C109.5C15C—C16C—H16G109.5
H16B—C16A—H16C109.5C15C—C16C—H16H109.5
N1A—C17A—C8A177.0 (5)H16G—C16C—H16H109.5
C2B—O1B—C1B117.26 (16)C15C—C16C—H16I109.5
C14B—N2B—C11B122.66 (18)H16G—C16C—H16I109.5
C14B—N2B—C12B117.30 (18)H16H—C16C—H16I109.5
C11B—N2B—C12B114.26 (18)N1B—C17B—C8B178.9 (4)
C2A—O1A—C1A—C9A38.2 (3)C1B—O1B—C2B—C3B153.4 (2)
C2A—O1A—C1A—C10A160.6 (2)C1B—O1B—C2B—C7B31.4 (3)
C2A—O1A—C1A—C13A84.2 (3)O1B—C2B—C3B—C4B175.5 (2)
C1A—O1A—C2A—C3A157.3 (3)C7B—C2B—C3B—C4B0.3 (4)
C1A—O1A—C2A—C7A27.4 (4)C2B—C3B—C4B—C5B0.7 (4)
O1A—C2A—C3A—C4A174.1 (3)C3B—C4B—C5B—C6B0.8 (4)
C7A—C2A—C3A—C4A1.1 (5)C4B—C5B—C6B—C7B0.1 (4)
C2A—C3A—C4A—C5A0.5 (6)C3B—C2B—C7B—C6B1.0 (3)
C3A—C4A—C5A—C6A0.8 (7)O1B—C2B—C7B—C6B176.04 (19)
C4A—C5A—C6A—C7A1.4 (6)C3B—C2B—C7B—C8B176.1 (2)
C5A—C6A—C7A—C2A0.8 (4)O1B—C2B—C7B—C8B1.1 (3)
C5A—C6A—C7A—C8A176.1 (3)C5B—C6B—C7B—C2B0.8 (3)
C3A—C2A—C7A—C6A0.4 (4)C5B—C6B—C7B—C8B176.0 (2)
O1A—C2A—C7A—C6A174.7 (2)C2B—C7B—C8B—C9B13.7 (3)
C3A—C2A—C7A—C8A177.5 (3)C6B—C7B—C8B—C9B169.4 (2)
O1A—C2A—C7A—C8A2.4 (4)C2B—C7B—C8B—C17B164.4 (2)
C6A—C7A—C8A—C9A173.9 (3)C6B—C7B—C8B—C17B12.5 (4)
C2A—C7A—C8A—C9A9.2 (4)C17B—C8B—C9B—C1B179.8 (2)
C6A—C7A—C8A—C17A7.6 (4)C7B—C8B—C9B—C1B2.1 (4)
C2A—C7A—C8A—C17A169.3 (2)O1B—C1B—C9B—C8B29.7 (3)
C17A—C8A—C9A—C1A177.4 (3)C10B—C1B—C9B—C8B145.8 (2)
C7A—C8A—C9A—C1A4.2 (4)C13B—C1B—C9B—C8B92.0 (3)
O1A—C1A—C9A—C8A26.8 (4)O1B—C1B—C10B—C11B62.5 (2)
C10A—C1A—C9A—C8A143.1 (3)C9B—C1B—C10B—C11B178.47 (19)
C13A—C1A—C9A—C8A94.6 (3)C13B—C1B—C10B—C11B54.9 (2)
O1A—C1A—C10A—C11A62.8 (3)C14B—N2B—C11B—C10B152.5 (2)
C9A—C1A—C10A—C11A176.5 (2)C12B—N2B—C11B—C10B55.1 (3)
C13A—C1A—C10A—C11A52.8 (3)C1B—C10B—C11B—N2B55.4 (3)
C14A—N2A—C11A—C10A158.1 (2)C14B—N2B—C12B—C13B151.31 (19)
C12A—N2A—C11A—C10A56.5 (3)C11B—N2B—C12B—C13B54.7 (3)
C1A—C10A—C11A—N2A56.3 (3)N2B—C12B—C13B—C1B53.9 (3)
C14A—N2A—C12A—C13A157.7 (2)O1B—C1B—C13B—C12B60.2 (2)
C11A—N2A—C12A—C13A54.9 (3)C9B—C1B—C13B—C12B178.10 (19)
N2A—C12A—C13A—C1A52.8 (3)C10B—C1B—C13B—C12B54.1 (2)
O1A—C1A—C13A—C12A61.0 (3)C15B—N3B—C14B—O2B13.1 (8)
C9A—C1A—C13A—C12A176.4 (3)C15C—N3B—C14B—O2B1.9 (11)
C10A—C1A—C13A—C12A51.0 (3)C15B—N3B—C14B—N2B171.4 (8)
C15A—N3A—C14A—O2A0.5 (4)C15C—N3B—C14B—N2B173.7 (10)
C15A—N3A—C14A—N2A177.4 (3)C11B—N2B—C14B—O2B173.9 (2)
C12A—N2A—C14A—O2A9.0 (4)C12B—N2B—C14B—O2B22.2 (3)
C11A—N2A—C14A—O2A153.3 (3)C11B—N2B—C14B—N3B10.5 (3)
C12A—N2A—C14A—N3A174.1 (2)C12B—N2B—C14B—N3B162.2 (2)
C11A—N2A—C14A—N3A29.8 (3)C14B—N3B—C15B—C16B162.7 (8)
C14A—N3A—C15A—C16A128.1 (4)C15C—N3B—C15B—C16B15 (3)
C2B—O1B—C1B—C9B43.8 (3)C14B—N3B—C15C—C16C106.6 (11)
C2B—O1B—C1B—C10B164.34 (18)C15B—N3B—C15C—C16C66 (4)
C2B—O1B—C1B—C13B78.8 (2)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C4B–C9B benzene ring
D—H···AD—HH···AD···AD—H···A
N3A—H1N3···O2Ai0.81 (3)2.12 (3)2.915 (3)170 (3)
N3B—H2N3···O2Bii0.83 (2)2.19 (3)2.983 (3)160 (2)
C11A—H11B···O2Ai1.00 (3)2.27 (3)3.246 (3)165 (2)
C11B—H11C···O2Bii0.95 (3)2.50 (3)3.344 (3)147 (2)
C9B—H9B···O2Biii0.92 (3)2.58 (3)3.473 (3)163 (2)
C13A—H13B···Cg1iv0.972.913.843 (3)163
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x, y+3/2, z1/2; (iii) x+2, y+1, z+2; (iv) x, y1/2, z3/2.

Experimental details

Crystal data
Chemical formulaC17H19N3O2
Mr297.35
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)22.7845 (8), 14.3370 (5), 9.8442 (3)
β (°) 90.783 (1)
V3)3215.42 (19)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.35 × 0.30 × 0.25
Data collection
DiffractometerBruker Kappa APEXII
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2008)
Tmin, Tmax0.972, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections
26353, 5377, 3664
Rint0.028
(sin θ/λ)max1)0.584
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.177, 1.04
No. of reflections5377
No. of parameters455
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.29, 0.20

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLUTON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C4B–C9B benzene ring
D—H···AD—HH···AD···AD—H···A
N3A—H1N3···O2Ai0.81 (3)2.12 (3)2.915 (3)170 (3)
N3B—H2N3···O2Bii0.83 (2)2.19 (3)2.983 (3)160 (2)
C11A—H11B···O2Ai1.00 (3)2.27 (3)3.246 (3)165 (2)
C11B—H11C···O2Bii0.95 (3)2.50 (3)3.344 (3)147 (2)
C9B—H9B···O2Biii0.92 (3)2.58 (3)3.473 (3)163 (2)
C13A—H13B···Cg1iv0.972.913.843 (3)163
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x, y+3/2, z1/2; (iii) x+2, y+1, z+2; (iv) x, y1/2, z3/2.
 

Acknowledgements

The authors thank the SAIF, IIT, Madras, India, for the X-ray intensity data collection facility.

References

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