5-tert-Butyl 3-ethyl 1-isopropyl-4,5,6,7-tetra­hydro-1H-pyrazolo­[4,3-c]pyridine-3,5-dicarboxyl­ate

Guo, H.-M.

doi:10.1107/S1600536811046332

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3239

https://doi.org/10.1107/S1600536811046332

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5-tert-Butyl 3-ethyl 1-isopropyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine-3,5-dicarboxylate

Huan-Mei Guo ^a ^*

^aMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: huanmeiguo@163.com

(Received 26 October 2011; accepted 3 November 2011; online 9 November 2011)

In the title compound, C₁₇H₂₇N₃O₄, the six-membered ring adopts a half-chair conformation with the N atom and the adjacent methylene C atom displaced by −0.391 (2) and 0.358 (2) Å, respectively, from the plane of the other four atoms. In the crystal, molecules are linked by weak C—H⋯O interactions.

Related literature

For a related structure and background references to heterocycles as pharmaceuticals, see: Guo (2011 ).

Experimental

Crystal data

C₁₇H₂₇N₃O₄
M_r = 337.42
Monoclinic, P 2₁ /c
a = 13.017 (3) Å
b = 12.771 (3) Å
c = 11.952 (3) Å
β = 115.760 (3)°
V = 1789.4 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 173 K
0.21 × 0.17 × 0.06 mm

Data collection

Rigaku MM007-HF CCD (Saturn 724+) diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ) T_min = 0.981, T_max = 0.995
7844 measured reflections
4013 independent reflections
3330 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.128
S = 1.09
4013 reflections
223 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5B⋯O1ⁱ	0.99	2.51	3.303 (3)	137
C11—H11A⋯O1ⁱⁱ	0.98	2.57	3.320 (3)	133
Symmetry codes: (i) -x+2, -y, -z+2; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811046332/hb6476sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811046332/hb6476Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811046332/hb6476Isup3.cml

checkCIF report

Comment top

As part of our ongoing studies of heterocycles (Guo, 2011), herein we report the structure of the title compound.

In the molecule (Fig. 1), all bond lengths and angles are within normal ranges.The atoms N1, N2, C1, C2, C3, C4 and C6 lie in a plan(p1), with a maximum deviation of 0.0100 (15)Å; atoms N3, C13, O3, O4, and C14 lie in a plan(p2) too, the maximum deviation is 0.0552 (12)Å. The dihedral angle between p1 and p2 is 75.44 (5)°.

Related literature top

For a related structure and background references to heterocycles as pharmaceuticals, see: Guo (2011).

Experimental top

The title compound was synthesized with 5-tert-butyl 3-ethyl 6,7-dihydro-1H- pyrazolo[4,3-c]pyridine-3,5(4H)- dicarboxylate (1 eq), NaH (2.5 eq) and 2-bromopropane (1.2 eq) in THF at 273 K to room temperature. Single crystals of the compound suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.

Structure description top

As part of our ongoing studies of heterocycles (Guo, 2011), herein we report the structure of the title compound.

For a related structure and background references to heterocycles as pharmaceuticals, see: Guo (2011).

Computing details top

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear (Rigaku, 2007); data reduction: CrystalClear (Rigaku, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.

5-tert-Butyl 3-ethyl 1-isopropyl-4,5,6,7-tetrahydro-1H- pyrazolo[4,3-c]pyridine-3,5-dicarboxylate top

Crystal data top

C₁₇H₂₇N₃O₄	F(000) = 728
M_r = 337.42	D_x = 1.252 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5928 reflections
a = 13.017 (3) Å	θ = 1.6–27.5°
b = 12.771 (3) Å	µ = 0.09 mm⁻¹
c = 11.952 (3) Å	T = 173 K
β = 115.760 (3)°	Block, colorless
V = 1789.4 (7) Å³	0.21 × 0.17 × 0.06 mm
Z = 4

Data collection top

Rigaku MM007-HF CCD (Saturn 724+) diffractometer	4013 independent reflections
Radiation source: rotating anode	3330 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.039
ω scans at fixed χ = 45°	θ_max = 27.4°, θ_min = 1.7°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	h = −16→14
T_min = 0.981, T_max = 0.995	k = −16→15
7844 measured reflections	l = −8→15

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0346P)² + 1.0152P] where P = (F_o² + 2F_c²)/3
4013 reflections	(Δ/σ)_max = 0.001
223 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₇H₂₇N₃O₄	V = 1789.4 (7) Å³
M_r = 337.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.017 (3) Å	µ = 0.09 mm⁻¹
b = 12.771 (3) Å	T = 173 K
c = 11.952 (3) Å	0.21 × 0.17 × 0.06 mm
β = 115.760 (3)°

Data collection top

Rigaku MM007-HF CCD (Saturn 724+) diffractometer	4013 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	3330 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.995	R_int = 0.039
7844 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.128	H-atom parameters constrained
S = 1.09	Δρ_max = 0.27 e Å⁻³
4013 reflections	Δρ_min = −0.22 e Å⁻³
223 parameters

Special details top

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	0.89479 (12)	0.21624 (10)	0.88381 (12)	0.0305 (3)
O2	0.83497 (11)	0.09119 (10)	0.73679 (11)	0.0270 (3)
O3	0.59568 (12)	−0.19414 (12)	0.66795 (13)	0.0379 (4)
O4	0.62019 (11)	−0.32250 (10)	0.80972 (12)	0.0272 (3)
N1	0.86219 (13)	−0.02179 (11)	1.09856 (13)	0.0214 (3)
N2	0.87328 (12)	0.06944 (11)	1.04856 (13)	0.0208 (3)
N3	0.77214 (13)	−0.23478 (12)	0.81927 (14)	0.0231 (3)
C1	0.86041 (14)	0.04334 (13)	0.93459 (16)	0.0191 (4)
C2	0.83954 (14)	−0.06483 (14)	0.91134 (16)	0.0194 (4)
C3	0.84147 (14)	−0.10378 (14)	1.01911 (16)	0.0202 (4)
C4	0.82646 (16)	−0.21603 (14)	1.04464 (17)	0.0236 (4)
H4A	0.7507	−0.2267	1.0436	0.028*
H4B	0.8859	−0.2369	1.1272	0.028*
C5	0.83677 (16)	−0.28141 (14)	0.94246 (17)	0.0241 (4)
H5B	0.9181	−0.2869	0.9595	0.029*
H5A	0.8080	−0.3530	0.9433	0.029*
C6	0.82002 (16)	−0.13484 (14)	0.80231 (17)	0.0245 (4)
H6A	0.7665	−0.1010	0.7241	0.029*
H6B	0.8930	−0.1474	0.7974	0.029*
C7	0.86696 (14)	0.12674 (14)	0.85268 (16)	0.0206 (4)
C8	0.83558 (18)	0.16686 (16)	0.64603 (17)	0.0307 (4)
H8B	0.9146	0.1795	0.6575	0.037*
H8A	0.8028	0.2342	0.6559	0.037*
C9	0.7652 (2)	0.12184 (19)	0.51993 (18)	0.0409 (5)
H9B	0.7695	0.1678	0.4565	0.061*
H9A	0.6856	0.1159	0.5067	0.061*
H9C	0.7943	0.0523	0.5141	0.061*
C10	0.85336 (16)	−0.02244 (14)	1.21705 (16)	0.0241 (4)
H10	0.8639	−0.0962	1.2482	0.029*
C11	0.94661 (17)	0.04410 (16)	1.31347 (17)	0.0298 (4)
H11B	1.0211	0.0209	1.3211	0.045*
H11C	0.9441	0.0366	1.3939	0.045*
H11A	0.9348	0.1177	1.2877	0.045*
C12	0.73472 (17)	0.01270 (18)	1.19462 (19)	0.0365 (5)
H12B	0.7229	0.0853	1.1652	0.055*
H12C	0.7267	0.0079	1.2723	0.055*
H12A	0.6779	−0.0324	1.1318	0.055*
C13	0.65564 (16)	−0.24563 (15)	0.75820 (17)	0.0246 (4)
C14	0.49694 (16)	−0.34246 (16)	0.76793 (18)	0.0293 (4)
C15	0.49744 (19)	−0.43108 (18)	0.8521 (2)	0.0433 (6)
H15A	0.4187	−0.4506	0.8330	0.065*
H15C	0.5368	−0.4085	0.9389	0.065*
H15B	0.5371	−0.4916	0.8389	0.065*
C16	0.44174 (18)	−0.3756 (2)	0.6327 (2)	0.0434 (6)
H16B	0.3628	−0.3971	0.6094	0.065*
H16C	0.4843	−0.4345	0.6207	0.065*
H16A	0.4425	−0.3167	0.5805	0.065*
C17	0.44277 (19)	−0.24554 (19)	0.7929 (2)	0.0410 (5)
H17A	0.4487	−0.1872	0.7428	0.062*
H17C	0.4823	−0.2273	0.8811	0.062*
H17B	0.3622	−0.2595	0.7708	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0424 (8)	0.0206 (7)	0.0280 (7)	−0.0067 (6)	0.0148 (6)	−0.0004 (5)
O2	0.0420 (8)	0.0206 (7)	0.0205 (6)	−0.0026 (6)	0.0154 (6)	0.0015 (5)
O3	0.0346 (8)	0.0423 (9)	0.0303 (8)	−0.0006 (7)	0.0079 (7)	0.0120 (7)
O4	0.0233 (7)	0.0266 (7)	0.0301 (7)	−0.0030 (5)	0.0099 (6)	0.0028 (6)
N1	0.0283 (8)	0.0172 (7)	0.0201 (7)	−0.0012 (6)	0.0119 (7)	0.0001 (6)
N2	0.0246 (8)	0.0177 (7)	0.0211 (7)	−0.0008 (6)	0.0108 (6)	0.0007 (6)
N3	0.0275 (8)	0.0192 (7)	0.0226 (8)	−0.0042 (6)	0.0110 (7)	−0.0027 (6)
C1	0.0179 (8)	0.0192 (9)	0.0202 (8)	−0.0008 (7)	0.0085 (7)	0.0001 (7)
C2	0.0199 (8)	0.0194 (9)	0.0198 (8)	−0.0022 (7)	0.0094 (7)	−0.0015 (7)
C3	0.0215 (9)	0.0183 (9)	0.0209 (8)	−0.0013 (7)	0.0092 (7)	−0.0012 (7)
C4	0.0294 (10)	0.0199 (9)	0.0219 (9)	−0.0032 (8)	0.0114 (8)	0.0010 (7)
C5	0.0263 (9)	0.0193 (9)	0.0248 (9)	−0.0005 (7)	0.0093 (8)	−0.0005 (7)
C6	0.0340 (10)	0.0205 (9)	0.0233 (9)	−0.0065 (8)	0.0164 (8)	−0.0037 (7)
C7	0.0191 (8)	0.0204 (9)	0.0225 (9)	0.0005 (7)	0.0093 (7)	0.0022 (7)
C8	0.0410 (12)	0.0279 (10)	0.0263 (10)	−0.0007 (9)	0.0176 (9)	0.0068 (8)
C9	0.0554 (14)	0.0414 (13)	0.0237 (10)	−0.0036 (11)	0.0152 (10)	0.0064 (9)
C10	0.0354 (10)	0.0223 (9)	0.0177 (8)	0.0003 (8)	0.0143 (8)	0.0017 (7)
C11	0.0368 (11)	0.0302 (11)	0.0210 (9)	0.0016 (9)	0.0113 (9)	−0.0022 (8)
C12	0.0343 (11)	0.0490 (13)	0.0320 (11)	−0.0023 (10)	0.0198 (9)	0.0007 (10)
C13	0.0285 (10)	0.0229 (9)	0.0231 (9)	−0.0023 (8)	0.0118 (8)	−0.0022 (8)
C14	0.0223 (9)	0.0337 (11)	0.0321 (10)	−0.0019 (8)	0.0121 (8)	−0.0006 (9)
C15	0.0356 (12)	0.0398 (13)	0.0555 (15)	−0.0079 (10)	0.0207 (11)	0.0071 (11)
C16	0.0289 (11)	0.0602 (16)	0.0395 (12)	−0.0135 (11)	0.0133 (10)	−0.0149 (11)
C17	0.0385 (12)	0.0445 (13)	0.0453 (13)	0.0071 (10)	0.0231 (11)	−0.0003 (11)

Geometric parameters (Å, º) top

O1—C7	1.208 (2)	C8—H8B	0.9900
O2—C7	1.340 (2)	C8—H8A	0.9900
O2—C8	1.455 (2)	C9—H9B	0.9800
O3—C13	1.214 (2)	C9—H9A	0.9800
O4—C13	1.343 (2)	C9—H9C	0.9800
O4—C14	1.480 (2)	C10—C12	1.516 (3)
N1—N2	1.345 (2)	C10—C11	1.519 (3)
N1—C3	1.360 (2)	C10—H10	1.0000
N1—C10	1.470 (2)	C11—H11B	0.9800
N2—C1	1.340 (2)	C11—H11C	0.9800
N3—C13	1.375 (2)	C11—H11A	0.9800
N3—C5	1.468 (2)	C12—H12B	0.9800
N3—C6	1.472 (2)	C12—H12C	0.9800
C1—C2	1.412 (2)	C12—H12A	0.9800
C1—C7	1.474 (2)	C14—C15	1.512 (3)
C2—C3	1.371 (2)	C14—C16	1.516 (3)
C2—C6	1.508 (2)	C14—C17	1.517 (3)
C3—C4	1.496 (2)	C15—H15A	0.9800
C4—C5	1.533 (2)	C15—H15C	0.9800
C4—H4A	0.9900	C15—H15B	0.9800
C4—H4B	0.9900	C16—H16B	0.9800
C5—H5B	0.9900	C16—H16C	0.9800
C5—H5A	0.9900	C16—H16A	0.9800
C6—H6A	0.9900	C17—H17A	0.9800
C6—H6B	0.9900	C17—H17C	0.9800
C8—C9	1.497 (3)	C17—H17B	0.9800

C7—O2—C8	116.44 (14)	C8—C9—H9C	109.5
C13—O4—C14	120.61 (14)	H9B—C9—H9C	109.5
N2—N1—C3	112.56 (14)	H9A—C9—H9C	109.5
N2—N1—C10	120.08 (14)	N1—C10—C12	109.16 (15)
C3—N1—C10	126.43 (15)	N1—C10—C11	110.89 (15)
C1—N2—N1	104.24 (14)	C12—C10—C11	112.66 (17)
C13—N3—C5	120.72 (15)	N1—C10—H10	108.0
C13—N3—C6	116.71 (15)	C12—C10—H10	108.0
C5—N3—C6	113.42 (14)	C11—C10—H10	108.0
N2—C1—C2	111.82 (15)	C10—C11—H11B	109.5
N2—C1—C7	118.53 (15)	C10—C11—H11C	109.5
C2—C1—C7	129.64 (16)	H11B—C11—H11C	109.5
C3—C2—C1	104.29 (15)	C10—C11—H11A	109.5
C3—C2—C6	121.62 (16)	H11B—C11—H11A	109.5
C1—C2—C6	134.09 (16)	H11C—C11—H11A	109.5
N1—C3—C2	107.09 (15)	C10—C12—H12B	109.5
N1—C3—C4	126.83 (15)	C10—C12—H12C	109.5
C2—C3—C4	126.07 (16)	H12B—C12—H12C	109.5
C3—C4—C5	107.16 (14)	C10—C12—H12A	109.5
C3—C4—H4A	110.3	H12B—C12—H12A	109.5
C5—C4—H4A	110.3	H12C—C12—H12A	109.5
C3—C4—H4B	110.3	O3—C13—O4	125.96 (18)
C5—C4—H4B	110.3	O3—C13—N3	123.52 (17)
H4A—C4—H4B	108.5	O4—C13—N3	110.48 (15)
N3—C5—C4	111.58 (15)	O4—C14—C15	102.34 (15)
N3—C5—H5B	109.3	O4—C14—C16	110.48 (15)
C4—C5—H5B	109.3	C15—C14—C16	111.31 (19)
N3—C5—H5A	109.3	O4—C14—C17	108.74 (16)
C4—C5—H5A	109.3	C15—C14—C17	110.36 (18)
H5B—C5—H5A	108.0	C16—C14—C17	113.07 (18)
N3—C6—C2	108.50 (14)	C14—C15—H15A	109.5
N3—C6—H6A	110.0	C14—C15—H15C	109.5
C2—C6—H6A	110.0	H15A—C15—H15C	109.5
N3—C6—H6B	110.0	C14—C15—H15B	109.5
C2—C6—H6B	110.0	H15A—C15—H15B	109.5
H6A—C6—H6B	108.4	H15C—C15—H15B	109.5
O1—C7—O2	123.77 (16)	C14—C16—H16B	109.5
O1—C7—C1	125.12 (17)	C14—C16—H16C	109.5
O2—C7—C1	111.09 (15)	H16B—C16—H16C	109.5
O2—C8—C9	107.22 (16)	C14—C16—H16A	109.5
O2—C8—H8B	110.3	H16B—C16—H16A	109.5
C9—C8—H8B	110.3	H16C—C16—H16A	109.5
O2—C8—H8A	110.3	C14—C17—H17A	109.5
C9—C8—H8A	110.3	C14—C17—H17C	109.5
H8B—C8—H8A	108.5	H17A—C17—H17C	109.5
C8—C9—H9B	109.5	C14—C17—H17B	109.5
C8—C9—H9A	109.5	H17A—C17—H17B	109.5
H9B—C9—H9A	109.5	H17C—C17—H17B	109.5

C3—N1—N2—C1	−0.73 (19)	C3—C2—C6—N3	16.5 (2)
C10—N1—N2—C1	−170.41 (15)	C1—C2—C6—N3	−164.66 (18)
N1—N2—C1—C2	0.77 (19)	C8—O2—C7—O1	0.4 (3)
N1—N2—C1—C7	179.55 (14)	C8—O2—C7—C1	178.84 (15)
N2—C1—C2—C3	−0.5 (2)	N2—C1—C7—O1	8.1 (3)
C7—C1—C2—C3	−179.14 (17)	C2—C1—C7—O1	−173.39 (18)
N2—C1—C2—C6	−179.51 (18)	N2—C1—C7—O2	−170.33 (15)
C7—C1—C2—C6	1.9 (3)	C2—C1—C7—O2	8.2 (3)
N2—N1—C3—C2	0.4 (2)	C7—O2—C8—C9	−163.00 (16)
C10—N1—C3—C2	169.31 (16)	N2—N1—C10—C12	75.7 (2)
N2—N1—C3—C4	179.00 (16)	C3—N1—C10—C12	−92.4 (2)
C10—N1—C3—C4	−12.1 (3)	N2—N1—C10—C11	−49.0 (2)
C1—C2—C3—N1	0.07 (18)	C3—N1—C10—C11	142.90 (17)
C6—C2—C3—N1	179.20 (15)	C14—O4—C13—O3	−8.2 (3)
C1—C2—C3—C4	−178.52 (17)	C14—O4—C13—N3	174.12 (15)
C6—C2—C3—C4	0.6 (3)	C5—N3—C13—O3	166.25 (18)
N1—C3—C4—C5	−165.31 (16)	C6—N3—C13—O3	21.5 (3)
C2—C3—C4—C5	13.0 (2)	C5—N3—C13—O4	−16.0 (2)
C13—N3—C5—C4	−77.8 (2)	C6—N3—C13—O4	−160.74 (14)
C6—N3—C5—C4	67.98 (19)	C13—O4—C14—C15	−178.30 (17)
C3—C4—C5—N3	−44.5 (2)	C13—O4—C14—C16	63.1 (2)
C13—N3—C6—C2	97.36 (18)	C13—O4—C14—C17	−61.5 (2)
C5—N3—C6—C2	−49.90 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5B···O1ⁱ	0.99	2.51	3.303 (3)	137
C11—H11A···O1ⁱⁱ	0.98	2.57	3.320 (3)	133

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

Experimental details

Crystal data
Chemical formula	C₁₇H₂₇N₃O₄
M_r	337.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	13.017 (3), 12.771 (3), 11.952 (3)
β (°)	115.760 (3)
V (Å³)	1789.4 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.21 × 0.17 × 0.06

Data collection
Diffractometer	Rigaku MM007-HF CCD (Saturn 724+)
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2007)
T_min, T_max	0.981, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	7844, 4013, 3330
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.128, 1.09
No. of reflections	4013
No. of parameters	223
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.22

Computer programs: CrystalClear (Rigaku, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5B···O1ⁱ	0.99	2.51	3.303 (3)	137
C11—H11A···O1ⁱⁱ	0.98	2.57	3.320 (3)	133

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

Acknowledgements

The author would like to thank Shandong Provincial Natural Science Foundation, China (Y2008B29) and Yuandu Scholar of Weifang City.

References

Guo, H.-M. (2011). Acta Cryst. E67, o2516. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 12| December 2011| Page o3239

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

5-tert-Butyl 3-ethyl 1-iso­propyl-4,5,6,7-tetra­hydro-1H-pyrazolo­[4,3-c]pyridine-3,5-di­carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

5-tert-Butyl 3-ethyl 1-isopropyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine-3,5-dicarboxylate