Tert-butyl 3-oxo-2,3,4,5,6,7-hexa­hydro-1H-pyrazolo[4,3-c]pyridine-5-carboxyl­ate

Shahani, T.; Fun, H.-K.; Ragavan, R.V.; Vijayakumar, V.; Sarveswari, S.

doi:10.1107/S1600536809053021

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 1| January 2010| Pages o142-o143

doi:10.1107/S1600536809053021

Open

access

Tert-butyl 3-oxo-2,3,4,5,6,7-hexahydro-1H-pyrazolo[4,3-c]pyridine-5-carboxylate

Tara Shahani,^a Hoong-Kun Fun,^a ^*‡ R. Venkat Ragavan,^b V. Vijayakumar ^b and S. Sarveswari ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bOrganic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, India
^*Correspondence e-mail: hkfun@usm.my

(Received 9 December 2009; accepted 9 December 2009; online 16 December 2009)

In the title compound, C₁₁H₁₇N₃O₃, the pyrazole ring is approximately planar, with a maximum deviation of 0.005 (2) Å, and forms a dihedral angle of 5.69 (13)° with the plane through the six atoms of the piperidine ring. In the crystal, pairs of intermolecular N—H⋯O hydrogen bonds form dimers with neighbouring molecules, generating R₂²(8) ring motifs. These dimers are further linked into two-dimensional arrays parallel to the bc plane by intermolecular N—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For the biological activity of pyrazolone derivatives, see: Al-Haiza et al. (2001 ); Brogden, (1986 ); Coersmeier et al. (1986 ); Gursoy et al. (2000 ). For myocardial ischemia, see: Wu et al. (2002 ). For brain ischemia, see: Watanabe et al. (1984 ); Kawai et al. (1997 ). For new compounds with the pyrazolone unit, see: Al-Haiza et al. (2001). For a related structure, see: Shahani et al. (2009 ). For ring conformations, see: Cremer & Pople (1975 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₁H₁₇N₃O₃
M_r = 239.28
Monoclinic, P 2₁ /c
a = 18.6250 (12) Å
b = 6.0893 (5) Å
c = 10.7414 (7) Å
β = 104.100 (4)°
V = 1181.51 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.97 × 0.35 × 0.14 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.910, T_max = 0.986
13101 measured reflections
2690 independent reflections
2136 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.172
S = 1.24
2690 reflections
222 parameters
All H-atom parameters refined
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O2ⁱ	0.99 (3)	1.77 (3)	2.748 (3)	171 (3)
N2—H1N2⋯O2ⁱⁱ	0.94 (3)	1.75 (4)	2.665 (3)	167 (3)
C1—H1B⋯O2ⁱⁱⁱ	0.98 (3)	2.57 (3)	3.492 (3)	157 (3)
C11—H11C⋯O3^iv	0.97 (3)	2.60 (3)	3.504 (3)	156 (3)
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x, -y+2, -z+1; (iii) x, y-1, z; (iv) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809053021/ng2705sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809053021/ng2705Isup2.hkl

checkCIF report

Comment top

Pyrazolone derivatives have a broad spectrum of biological activities being used as analgesic, antipyretic and anti-inflammatory therapeutical drugs (Brogden, 1986; Gursoy et al., 2000). A class of new compounds with pyrazolone moiety was synthesized and reported for their antibacterial, antifungal activities by Al-Haiza et al. (2001). A new pyrazolone derivative, edaravone (3-methyl-1-phenyl-2-pyrazoline-5-one) is being used as a drug in clinical practice for brain ischemia (Watanabe et al., 1984; Kawai et al., 1997) and the same has been found to be effective against myocardial ischemia (Wu et al., 2002).

In the crystal structure (Fig. 1), the pyrazole ring (C3/N1/N2/C4/C5) is approximately planar, with a maximum deviation of 0.005 (2) Å at atom N2. The piperidine ring (C1/C2/C3/C5/C6/N3) adopts a half-boat conformation (Cremer & Pople, 1975) with puckering of Q = 0.465 (2) Å, Θ = 52.9 (2)° & ϕ = 39.8 (4)°. The maximum deviation in this piperidine ring is 0.286 Å at atom N3. The dihedral angle formed between the mean planes of pyrazole and piperidine rings is 5.69 (13)°. The bond lengths (Allen et al., 1987) and angles are within normal ranges and comparable to a closely related structure (Shahani et al., 2009).

In the crystal packing (Fig. 2), pairs of intermolecular N2—H1N2···O2 hydrogen bonds form dimers with neighbouring molecules, generating R²₂(8) ring motifs (Bernstein et al., 1995). These dimers are further linked into two-dimensional arrays parallel to the bc plane by intermolecular N1—H1N1···O2, C1—H1B···O2 and C11—H11C···O3 hydrogen bonds.

Related literature top

For the biological activity of pyrazolone derivatives, see: Al-Haiza et al. (2001); Brogden, (1986); Coersmeier et al. (1986); Gursoy et al. (2000). For myocardial ischemia, see: Wu et al. (2002). For brain ischemia, see: Watanabe et al. (1984); Kawai et al. (1997). For new compounds with the pyrazolone unit, see: Al-Haiza et al. (2001). For a related structure, see: Shahani et al. (2009). For ring conformations, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

LiHMDS (1.0 M solution in toluene, 11 mmol) was added quickly to a solution of tert-butyl 4-oxopiperidine-1-carboxylate (10 mmol 15 ml of toluene) using syringe at 273 K with stirring for 10 minutes. Ethyl chloro formate (11 mmol) was then added quickly. The reaction mixture was slowly (10 minutes) brought to room temperature and stirred for 10 minutes. Acetic acid (2 ml), ethanol (15 ml), and hydrazine hydrate (30 mmol) were added and refluxed for 15 minutes. The reaction mixture was concentrated to dryness under reduced pressure and re-dissolved in ethyl acetate. The organic layer was washed with saturated brine solution, dried over Na₂SO₄, evaporated under reduced pressure and purified by crystallizing using ethanol (white solid). The recrystallization was done using 1:1 mixture of ethanol and acetone. Yield: 78%. M.p. 498.5–500.5 K. MS calculated for C₁₁H₁₇N₃O₃: 239.126. Found: 239.80 (M+).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom numbering scheme.
	Fig. 2. The crystal packing of the title compound, viewed along b axis, showing two-dimensional arrays parallel to the bc plane.

Tert-butyl 3-oxo-2,3,4,5,6,7-hexahydro-1H- pyrazolo[4,3-c]pyridine-5-carboxylate top

Crystal data top

C₁₁H₁₇N₃O₃	F(000) = 512
M_r = 239.28	D_x = 1.345 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7287 reflections
a = 18.6250 (12) Å	θ = 2.3–33.5°
b = 6.0893 (5) Å	µ = 0.10 mm⁻¹
c = 10.7414 (7) Å	T = 100 K
β = 104.100 (4)°	Plate, colourless
V = 1181.51 (15) Å³	0.97 × 0.35 × 0.14 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2690 independent reflections
Radiation source: fine-focus sealed tube	2136 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −24→24
T_min = 0.910, T_max = 0.986	k = −7→7
13101 measured reflections	l = −13→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.172	All H-atom parameters refined
S = 1.24	w = 1/[σ²(F_o²) + (0.0688P)² + 1.2823P] where P = (F_o² + 2F_c²)/3
2690 reflections	(Δ/σ)_max < 0.001
222 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₁H₁₇N₃O₃	V = 1181.51 (15) Å³
M_r = 239.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 18.6250 (12) Å	µ = 0.10 mm⁻¹
b = 6.0893 (5) Å	T = 100 K
c = 10.7414 (7) Å	0.97 × 0.35 × 0.14 mm
β = 104.100 (4)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2690 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2136 reflections with I > 2σ(I)
T_min = 0.910, T_max = 0.986	R_int = 0.035
13101 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.172	All H-atom parameters refined
S = 1.24	Δρ_max = 0.39 e Å⁻³
2690 reflections	Δρ_min = −0.31 e Å⁻³
222 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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

	x	y	z	U_iso*/U_eq
O1	0.30793 (9)	0.5995 (3)	0.33483 (16)	0.0205 (4)
O2	0.04609 (9)	0.9437 (3)	0.36561 (15)	0.0205 (4)
O3	0.34752 (9)	0.2971 (3)	0.45801 (16)	0.0231 (4)
N1	0.07659 (11)	0.5955 (4)	0.62882 (18)	0.0191 (4)
N2	0.04170 (11)	0.7682 (4)	0.55702 (19)	0.0186 (4)
N3	0.23023 (11)	0.4313 (3)	0.43120 (19)	0.0191 (4)
C1	0.20586 (14)	0.2460 (4)	0.4972 (2)	0.0215 (5)
C2	0.17706 (14)	0.3233 (4)	0.6127 (2)	0.0225 (5)
C3	0.12708 (12)	0.5145 (4)	0.5701 (2)	0.0185 (5)
C4	0.06920 (12)	0.7945 (4)	0.4514 (2)	0.0167 (5)
C5	0.12428 (12)	0.6319 (4)	0.4598 (2)	0.0172 (5)
C6	0.17364 (13)	0.5912 (4)	0.3715 (2)	0.0190 (5)
C7	0.30029 (12)	0.4308 (4)	0.4123 (2)	0.0180 (5)
C8	0.38126 (12)	0.6603 (4)	0.3140 (2)	0.0186 (5)
C9	0.43236 (15)	0.7313 (5)	0.4403 (3)	0.0258 (6)
C10	0.36107 (14)	0.8534 (5)	0.2231 (3)	0.0249 (6)
C11	0.41358 (14)	0.4723 (5)	0.2519 (2)	0.0215 (5)
H1A	0.2501 (16)	0.144 (5)	0.527 (3)	0.027 (7)*
H1B	0.1645 (16)	0.173 (5)	0.437 (3)	0.025 (7)*
H2A	0.1514 (16)	0.203 (6)	0.639 (3)	0.032 (8)*
H2B	0.2187 (16)	0.364 (5)	0.682 (3)	0.026 (7)*
H6A	0.1980 (15)	0.727 (5)	0.353 (3)	0.023 (7)*
H6B	0.1445 (14)	0.539 (5)	0.286 (3)	0.021 (7)*
H9A	0.4124 (16)	0.854 (5)	0.476 (3)	0.026 (8)*
H9B	0.4808 (16)	0.779 (5)	0.428 (3)	0.026 (7)*
H9C	0.4426 (16)	0.611 (6)	0.504 (3)	0.035 (9)*
H10A	0.4080 (17)	0.909 (5)	0.201 (3)	0.035 (8)*
H10B	0.3254 (17)	0.809 (5)	0.139 (3)	0.033 (8)*
H10C	0.3394 (19)	0.970 (6)	0.264 (3)	0.049 (10)*
H11A	0.4596 (16)	0.530 (5)	0.227 (3)	0.031 (8)*
H11B	0.4299 (15)	0.344 (5)	0.313 (3)	0.027 (7)*
H11C	0.3819 (18)	0.421 (6)	0.172 (3)	0.042 (9)*
H1N1	0.0676 (18)	0.566 (6)	0.714 (3)	0.043 (9)*
H1N2	0.0081 (18)	0.852 (6)	0.589 (3)	0.046 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0230 (8)	0.0192 (9)	0.0230 (8)	0.0028 (7)	0.0124 (6)	0.0066 (7)
O2	0.0288 (8)	0.0201 (9)	0.0164 (8)	0.0054 (7)	0.0128 (6)	0.0019 (7)
O3	0.0267 (8)	0.0206 (10)	0.0245 (9)	0.0053 (7)	0.0109 (7)	0.0061 (8)
N1	0.0267 (10)	0.0186 (11)	0.0152 (9)	−0.0001 (8)	0.0111 (7)	0.0008 (8)
N2	0.0246 (9)	0.0184 (11)	0.0160 (9)	0.0018 (8)	0.0110 (7)	0.0002 (8)
N3	0.0250 (10)	0.0148 (11)	0.0210 (10)	0.0028 (8)	0.0121 (8)	0.0043 (9)
C1	0.0285 (12)	0.0144 (12)	0.0253 (12)	0.0000 (10)	0.0138 (10)	0.0016 (11)
C2	0.0299 (12)	0.0177 (13)	0.0237 (12)	0.0001 (10)	0.0134 (10)	0.0069 (11)
C3	0.0235 (11)	0.0153 (12)	0.0192 (11)	−0.0036 (9)	0.0103 (9)	−0.0027 (10)
C4	0.0212 (10)	0.0163 (12)	0.0153 (10)	−0.0027 (9)	0.0099 (8)	−0.0018 (9)
C5	0.0224 (10)	0.0151 (12)	0.0164 (10)	−0.0015 (9)	0.0094 (8)	−0.0019 (9)
C6	0.0259 (11)	0.0182 (13)	0.0166 (11)	0.0041 (10)	0.0121 (9)	0.0014 (10)
C7	0.0244 (11)	0.0150 (12)	0.0167 (10)	0.0001 (10)	0.0089 (8)	−0.0012 (10)
C8	0.0222 (11)	0.0162 (12)	0.0213 (11)	−0.0014 (9)	0.0127 (9)	0.0010 (10)
C9	0.0327 (13)	0.0248 (15)	0.0224 (13)	−0.0028 (11)	0.0115 (10)	−0.0041 (12)
C10	0.0298 (12)	0.0237 (14)	0.0250 (13)	0.0024 (11)	0.0140 (10)	0.0053 (11)
C11	0.0265 (12)	0.0208 (13)	0.0198 (12)	0.0023 (10)	0.0106 (9)	−0.0032 (11)

Geometric parameters (Å, º) top

O1—C7	1.351 (3)	C3—C5	1.374 (3)
O1—C8	1.484 (3)	C4—C5	1.413 (3)
O2—C4	1.290 (3)	C5—C6	1.494 (3)
O3—C7	1.212 (3)	C6—H6A	0.98 (3)
N1—C3	1.347 (3)	C6—H6B	1.00 (3)
N1—N2	1.371 (3)	C8—C10	1.516 (4)
N1—H1N1	0.99 (3)	C8—C9	1.518 (4)
N2—C4	1.364 (3)	C8—C11	1.521 (3)
N2—H1N2	0.94 (4)	C9—H9A	0.96 (3)
N3—C7	1.369 (3)	C9—H9B	0.99 (3)
N3—C1	1.462 (3)	C9—H9C	0.99 (3)
N3—C6	1.463 (3)	C10—H10A	1.02 (3)
C1—C2	1.540 (3)	C10—H10B	1.02 (3)
C1—H1A	1.02 (3)	C10—H10C	0.97 (4)
C1—H1B	0.98 (3)	C11—H11A	1.02 (3)
C2—C3	1.491 (4)	C11—H11B	1.02 (3)
C2—H2A	0.95 (3)	C11—H11C	0.97 (3)
C2—H2B	0.97 (3)

C7—O1—C8	121.42 (18)	N3—C6—H6A	109.1 (16)
C3—N1—N2	107.86 (19)	C5—C6—H6A	111.8 (17)
C3—N1—H1N1	132 (2)	N3—C6—H6B	111.4 (16)
N2—N1—H1N1	120 (2)	C5—C6—H6B	110.9 (15)
C4—N2—N1	109.62 (19)	H6A—C6—H6B	105 (2)
C4—N2—H1N2	132 (2)	O3—C7—O1	125.9 (2)
N1—N2—H1N2	118 (2)	O3—C7—N3	124.4 (2)
C7—N3—C1	119.4 (2)	O1—C7—N3	109.70 (19)
C7—N3—C6	123.2 (2)	O1—C8—C10	101.39 (18)
C1—N3—C6	116.77 (19)	O1—C8—C9	109.63 (18)
N3—C1—C2	111.4 (2)	C10—C8—C9	111.0 (2)
N3—C1—H1A	107.4 (17)	O1—C8—C11	110.8 (2)
C2—C1—H1A	110.2 (16)	C10—C8—C11	111.3 (2)
N3—C1—H1B	108.7 (17)	C9—C8—C11	112.2 (2)
C2—C1—H1B	107.2 (16)	C8—C9—H9A	111.1 (17)
H1A—C1—H1B	112 (2)	C8—C9—H9B	110.9 (16)
C3—C2—C1	107.8 (2)	H9A—C9—H9B	106 (2)
C3—C2—H2A	111.7 (19)	C8—C9—H9C	112.3 (19)
C1—C2—H2A	107.4 (19)	H9A—C9—H9C	110 (2)
C3—C2—H2B	111.2 (19)	H9B—C9—H9C	106 (2)
C1—C2—H2B	108.9 (17)	C8—C10—H10A	108.3 (18)
H2A—C2—H2B	110 (3)	C8—C10—H10B	111.7 (19)
N1—C3—C5	109.2 (2)	H10A—C10—H10B	107 (2)
N1—C3—C2	126.6 (2)	C8—C10—H10C	110 (2)
C5—C3—C2	124.1 (2)	H10A—C10—H10C	110 (3)
O2—C4—N2	123.3 (2)	H10B—C10—H10C	110 (3)
O2—C4—C5	130.5 (2)	C8—C11—H11A	107.7 (18)
N2—C4—C5	106.2 (2)	C8—C11—H11B	112.6 (17)
C3—C5—C4	107.13 (19)	H11A—C11—H11B	107 (2)
C3—C5—C6	124.1 (2)	C8—C11—H11C	114 (2)
C4—C5—C6	128.7 (2)	H11A—C11—H11C	105 (3)
N3—C6—C5	108.74 (19)	H11B—C11—H11C	110 (3)

C3—N1—N2—C4	1.0 (3)	O2—C4—C5—C6	2.0 (4)
C7—N3—C1—C2	125.7 (2)	N2—C4—C5—C6	−177.9 (2)
C6—N3—C1—C2	−63.6 (3)	C7—N3—C6—C5	−148.5 (2)
N3—C1—C2—C3	45.8 (3)	C1—N3—C6—C5	41.2 (3)
N2—N1—C3—C5	−0.9 (3)	C3—C5—C6—N3	−7.8 (3)
N2—N1—C3—C2	−178.8 (2)	C4—C5—C6—N3	170.1 (2)
C1—C2—C3—N1	162.0 (2)	C8—O1—C7—O3	−10.1 (4)
C1—C2—C3—C5	−15.7 (3)	C8—O1—C7—N3	170.38 (19)
N1—N2—C4—O2	179.3 (2)	C1—N3—C7—O3	−8.0 (4)
N1—N2—C4—C5	−0.8 (3)	C6—N3—C7—O3	−178.1 (2)
N1—C3—C5—C4	0.4 (3)	C1—N3—C7—O1	171.5 (2)
C2—C3—C5—C4	178.4 (2)	C6—N3—C7—O1	1.4 (3)
N1—C3—C5—C6	178.6 (2)	C7—O1—C8—C10	−179.8 (2)
C2—C3—C5—C6	−3.4 (4)	C7—O1—C8—C9	−62.4 (3)
O2—C4—C5—C3	−179.8 (2)	C7—O1—C8—C11	61.9 (3)
N2—C4—C5—C3	0.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2ⁱ	0.99 (3)	1.77 (3)	2.748 (3)	171 (3)
N2—H1N2···O2ⁱⁱ	0.94 (3)	1.75 (4)	2.665 (3)	167 (3)
C1—H1B···O2ⁱⁱⁱ	0.98 (3)	2.57 (3)	3.492 (3)	157 (3)
C11—H11C···O3^iv	0.97 (3)	2.60 (3)	3.504 (3)	156 (3)

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x, −y+2, −z+1; (iii) x, y−1, z; (iv) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₇N₃O₃
M_r	239.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	18.6250 (12), 6.0893 (5), 10.7414 (7)
β (°)	104.100 (4)
V (Å³)	1181.51 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.97 × 0.35 × 0.14

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.910, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	13101, 2690, 2136
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.172, 1.24
No. of reflections	2690
No. of parameters	222
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.31

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2ⁱ	0.99 (3)	1.77 (3)	2.748 (3)	171 (3)
N2—H1N2···O2ⁱⁱ	0.94 (3)	1.75 (4)	2.665 (3)	167 (3)
C1—H1B···O2ⁱⁱⁱ	0.98 (3)	2.57 (3)	3.492 (3)	157 (3)
C11—H11C···O3^iv	0.97 (3)	2.60 (3)	3.504 (3)	156 (3)

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x, −y+2, −z+1; (iii) x, y−1, z; (iv) x, −y+1/2, z−1/2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and TSH thank Universiti Sains Malaysia (USM) for the Research University Golden Goose Grant (1001/PFIZIK/811012). VV is grateful to DST-India for funding through the Young Scientist Scheme (Fast Track Proposal).

References

Al-Haiza, M. A., El-Assiery, S. A. & Sayed, G. H. (2001). Acta Pharm. 51, 251–261. CAS Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Brogden, R. N. (1986). Drugs, 32, 60–70. CrossRef PubMed Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wiscosin, USA. Google Scholar
Coersmeier, C., Wittenberg, H. R., Aehringhaus, U., Dreyling, K. W., Peskar, B. M., Brune, K. & Pesker, B. A. (1986). Agents Actions Suppl. 19, 137–153. CAS PubMed Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Gursoy, A., Demirayak, S., Capan, G., Erol, K. & Vural, K. (2000). Eur. J. Med. Chem. 35, 359–364. Web of Science CrossRef PubMed CAS Google Scholar
Kawai, H., Nakai, H., Suga, M., Yuki, S., Watanabe, T. & Saito, K. I. (1997). J. Pharmcol. Exp. Ther. 281, 921–927. CAS Google Scholar
Shahani, T., Fun, H.-K., Ragavan, R. V., Vijayakumar, V. & Sarveswari, S. (2009). Acta Cryst. E65, o3249–o3250. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Watanabe, T., Yuki, S., Egawa, M. & Nishi, H. (1984). J. Pharmacol. Exp. Ther. 268, 1597–1604. Google Scholar
Wu, T. W., Zeng, L. H., Wu, J. & Fung, K. P. (2002). Life Sci. 71, 2249–2255. Web of Science CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 1| January 2010| Pages o142-o143

doi:10.1107/S1600536809053021

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

Tert-butyl 3-oxo-2,3,4,5,6,7-hexa­hydro-1H-pyrazolo[4,3-c]pyridine-5-carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

Tert-butyl 3-oxo-2,3,4,5,6,7-hexahydro-1H-pyrazolo[4,3-c]pyridine-5-carboxylate