5-tert-Butyl 1-ethyl 3-amino-1,4,5,6-tetra­hydro­pyrrolo­[3,4-c]pyrazole-1,5-dicarboxyl­ate

Xia, W.-B.; Bai, X.-G.; Liu, H.-T.; Wang, J.-X.

doi:10.1107/S1600536811013444

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1150

doi:10.1107/S1600536811013444

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5-tert-Butyl 1-ethyl 3-amino-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole-1,5-dicarboxylate

Wen-Bin Xia,^a Xiao-Guang Bai,^b Hong-Tao Liu ^b and Ju-Xian Wang ^b ^*

^aSchool of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, People's Republic of China, and ^bInstitute of Medicinal Biotechnology, Chinese Academy of Medical Sciences, and Peking Union Medical College, Beijing 100050, People's Republic of China
^*Correspondence e-mail: imbjxwang@gmail.com

(Received 29 March 2011; accepted 11 April 2011; online 16 April 2011)

The asymmetric unit of the title compound, C₁₃H₂₀N₄O₄, contains two crystallographically independent molecules in which the dihedral angles between the fused pyrrole and pyrazole rings are 5.06 (8) and 1.12 (8)°. In the crystal, molecules are linked by intermolecular N—H⋯O and N—H⋯N hydrogen bonds into chains parallel to the b axis.

Related literature

For general background to potential anticancer kinase inhibitors, see: Fancelli et al. (2005 ); Gadekar et al. (1968 ). For the structure of a related compound synthesized by our group, see: Guo et al. (2010 ).

Experimental

Crystal data

C₁₃H₂₀N₄O₄
M_r = 296.33
Triclinic, $[P \overline 1]$
a = 10.772 (3) Å
b = 12.180 (4) Å
c = 12.986 (4) Å
α = 70.845 (5)°
β = 65.875 (4)°
γ = 85.821 (5)°
V = 1465.2 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.06 × 0.05 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.994, T_max = 0.996
7444 measured reflections
5102 independent reflections
3915 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.128
S = 1.03
5102 reflections
387 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N8—H8"⋯O4ⁱ	0.86	2.25	3.069 (3)	160
N8—H8′⋯N2ⁱⁱ	0.86	2.26	3.087 (3)	163
N4—H4′⋯N6ⁱⁱⁱ	0.90	2.25	3.104 (3)	157
N4—H4"⋯O8^iv	0.90	2.36	3.233 (3)	163
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1, z; (iii) x-1, y-1, z; (iv) x-1, y, z.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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 I, global. DOI: 10.1107/S1600536811013444/rz2580sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811013444/rz2580Isup2.hkl

checkCIF report

Comment top

As an extension of our work (Guo et al., 2010) on the development of potential anticancer kinase inhibitors (Fancelli et al., 2005; Gadekar et al., 1968), we have synthesized the title compound and report its crystal structure herein.

The asymmetric unit of the title compound (Fig. 1) contains two crystallographically independent molecules. All bond lengths and angles have normal values. The dihedral angles between the fused pyrrole and pyrazole rings are 5.06 (8) and 1.12 (8)°. The C6/O1/O2/C7 and C9/O4/O3/C10 mean planes form dihedral angles of 5.83(0.09)° and 14.86(0.10) °, respectively, with the mean plane through N1/N2/C2/C1/C3/C4/C5/N3, whereas the O8/C22/O7/C23 and C18/O5/O6/C17 mean planes form dihedral angles of 6.20(0.12) ° and 5.12(0.13) °, respectively, with the N5/N6/C14/C15/C16/C20/C21/N7 mean plane. In the crystal structure (Fig.2), molecules are linked by intermolecular N—H···O and N—H···N hydrogen bonds (Table 1) to form chains running parallel to the b axis.

Related literature top

For general background to potential anticancer kinase inhibitors, see: Fancelli et al. (2005); Gadekar et al. (1968). For the structure of a related compound synthesized by our group, see: Guo et al. (2010).

Experimental top

A solution of ethyl chlorocarbonate (2.90 g, 12 mmol) in THF (30 ml) was slowly added dropwise to a mixture of tert-butyl 3-aminopyrrolo[3,4-c]pyrazole-5(1H,4H,6H)-carboxylate (3.3 g, 11 mmol) and DIEA (8.54 g, 66 mmol) in THF (60 ml) at 0~5 °C. The reaction was kept at the same temperature for 2 h, allowed to reach r.t., and stirred overnight. The obtained mixture was evaporated to dryness and the resulting residue extracted with AcOEt and water. The organic layer was separated, dried over sodium sulfate, and evaporated to dryness. The residue was purified by flash chromatography to give 1.8 g (55%) of the title compound as a white solid. Colourless block crystals suitable for X-ray diffraction were obtained in 2 days by slow evaporation of a methanol solution.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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.
	Fig. 2. Packing diagram of the title compound viewed along the c axis. Hydrogen bonds are shown as dashed lines.

5-tert-Butyl 1-ethyl 3-amino-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole-1,5-dicarboxylate top

Crystal data top

C₁₃H₂₀N₄O₄	Z = 4
M_r = 296.33	F(000) = 632
Triclinic, P1	D_x = 1.343 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.772 (3) Å	Cell parameters from 2737 reflections
b = 12.180 (4) Å	θ = 2.6–28.0°
c = 12.986 (4) Å	µ = 0.10 mm⁻¹
α = 70.845 (5)°	T = 296 K
β = 65.875 (4)°	Block, colourless
γ = 85.821 (5)°	0.06 × 0.05 × 0.04 mm
V = 1465.2 (7) Å³

Data collection top

Bruker APEXII CCD diffractometer	5102 independent reflections
Radiation source: fine-focus sealed tube	3915 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→10
T_min = 0.994, T_max = 0.996	k = −12→14
7444 measured reflections	l = −15→10

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0632P)² + 0.4323P] where P = (F_o² + 2F_c²)/3
5102 reflections	(Δ/σ)_max < 0.001
387 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₃H₂₀N₄O₄	γ = 85.821 (5)°
M_r = 296.33	V = 1465.2 (7) Å³
Triclinic, P1	Z = 4
a = 10.772 (3) Å	Mo Kα radiation
b = 12.180 (4) Å	µ = 0.10 mm⁻¹
c = 12.986 (4) Å	T = 296 K
α = 70.845 (5)°	0.06 × 0.05 × 0.04 mm
β = 65.875 (4)°

Data collection top

Bruker APEXII CCD diffractometer	5102 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3915 reflections with I > 2σ(I)
T_min = 0.994, T_max = 0.996	R_int = 0.026
7444 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.128	H-atom parameters constrained
S = 1.03	Δρ_max = 0.26 e Å⁻³
5102 reflections	Δρ_min = −0.32 e Å⁻³
387 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	0.26829 (15)	0.40073 (13)	0.06447 (14)	0.0348 (4)
O2	0.15420 (17)	0.22918 (13)	0.11483 (14)	0.0383 (4)
O3	0.18836 (13)	0.80172 (12)	0.11637 (12)	0.0248 (3)
O4	−0.02679 (14)	0.86224 (13)	0.15737 (14)	0.0303 (4)
O5	0.28280 (14)	1.06702 (13)	0.45631 (14)	0.0333 (4)
O6	0.39625 (15)	1.23659 (13)	0.41233 (14)	0.0348 (4)
O7	0.33735 (13)	0.66947 (12)	0.40945 (12)	0.0263 (3)
O8	0.54850 (14)	0.63169 (12)	0.29063 (12)	0.0264 (3)
N1	0.04383 (17)	0.39313 (15)	0.13325 (15)	0.0266 (4)
N2	−0.08554 (17)	0.34058 (15)	0.17464 (16)	0.0278 (4)
N3	0.03062 (16)	0.69338 (14)	0.12056 (15)	0.0252 (4)
N4	−0.30512 (18)	0.40713 (16)	0.22648 (17)	0.0334 (5)
H4"	−0.3627	0.4607	0.2482	0.050*
H4'	−0.3438	0.3339	0.2641	0.050*
N5	0.50579 (16)	1.08232 (14)	0.36264 (15)	0.0240 (4)
N6	0.63493 (17)	1.14050 (15)	0.30111 (15)	0.0259 (4)
N7	0.51226 (16)	0.79033 (14)	0.34994 (15)	0.0238 (4)
N8	0.85181 (18)	1.08823 (16)	0.19749 (17)	0.0363 (5)
H8'	0.8873	1.1559	0.1818	0.044*
H8"	0.9026	1.0366	0.1726	0.044*
C1	0.0358 (2)	0.50843 (17)	0.12258 (17)	0.0240 (5)
C2	−0.1695 (2)	0.42522 (18)	0.18909 (18)	0.0265 (5)
C3	−0.0945 (2)	0.53222 (18)	0.15632 (18)	0.0239 (5)
C4	−0.1110 (2)	0.65547 (17)	0.15288 (19)	0.0252 (5)
H4D	−0.1435	0.6998	0.0929	0.030*
H4E	−0.1721	0.6611	0.2300	0.030*
C5	0.1312 (2)	0.60819 (17)	0.08967 (18)	0.0247 (5)
H5A	0.1848	0.5907	0.1369	0.030*
H5B	0.1914	0.6337	0.0054	0.030*
C6	0.1580 (2)	0.33069 (19)	0.10486 (18)	0.0289 (5)
C7	0.3986 (2)	0.3522 (2)	0.0194 (2)	0.0403 (6)
H7A	0.4667	0.4144	−0.0399	0.048*
H7B	0.3917	0.2983	−0.0191	0.048*
C8	0.4422 (3)	0.2901 (3)	0.1178 (2)	0.0500 (7)
H8D	0.4388	0.3408	0.1619	0.075*
H8E	0.5337	0.2679	0.0845	0.075*
H8F	0.3822	0.2218	0.1703	0.075*
C9	0.0578 (2)	0.79265 (17)	0.13261 (18)	0.0233 (5)
C10	0.24457 (19)	0.90541 (17)	0.12164 (18)	0.0230 (5)
C11	0.3866 (2)	0.87316 (18)	0.10925 (19)	0.0286 (5)
H11A	0.3815	0.8011	0.1707	0.043*
H11B	0.4315	0.9335	0.1168	0.043*
H11C	0.4371	0.8643	0.0324	0.043*
C12	0.1652 (2)	0.9233 (2)	0.24050 (18)	0.0303 (5)
H12A	0.0756	0.9455	0.2468	0.046*
H12B	0.2116	0.9837	0.2466	0.046*
H12C	0.1577	0.8522	0.3038	0.046*
C13	0.2481 (2)	1.00881 (18)	0.01703 (18)	0.0279 (5)
H13A	0.2999	0.9927	−0.0559	0.042*
H13B	0.2899	1.0760	0.0166	0.042*
H13C	0.1567	1.0235	0.0239	0.042*
C14	0.7175 (2)	1.06333 (17)	0.26074 (18)	0.0242 (5)
C15	0.6416 (2)	0.95619 (17)	0.29503 (17)	0.0223 (4)
C16	0.5126 (2)	0.97181 (17)	0.35743 (17)	0.0226 (4)
C17	0.3930 (2)	1.13870 (19)	0.41168 (18)	0.0272 (5)
C18	0.1527 (2)	1.1110 (2)	0.5106 (2)	0.0393 (6)
H18A	0.1624	1.1630	0.5500	0.047*
H18B	0.0880	1.0467	0.5704	0.047*
C19	0.0999 (3)	1.1747 (3)	0.4194 (2)	0.0500 (7)
H19A	0.1563	1.2452	0.3675	0.075*
H19B	0.0080	1.1935	0.4585	0.075*
H19C	0.1014	1.1266	0.3734	0.075*
C20	0.4166 (2)	0.86791 (17)	0.40609 (18)	0.0245 (5)
H20A	0.3799	0.8369	0.4926	0.029*
H20B	0.3426	0.8839	0.3802	0.029*
C21	0.65594 (19)	0.83642 (17)	0.28762 (18)	0.0227 (4)
H21A	0.6951	0.8374	0.2055	0.027*
H21B	0.7108	0.7922	0.3283	0.027*
C22	0.4724 (2)	0.69102 (17)	0.34557 (17)	0.0223 (4)
C23	0.2682 (2)	0.55632 (18)	0.43977 (19)	0.0269 (5)
C24	0.3325 (2)	0.45964 (18)	0.5035 (2)	0.0318 (5)
H24A	0.4243	0.4547	0.4499	0.048*
H24B	0.2809	0.3872	0.5303	0.048*
H24C	0.3335	0.4753	0.5710	0.048*
C25	0.2688 (2)	0.5414 (2)	0.3285 (2)	0.0366 (6)
H25A	0.2313	0.6073	0.2891	0.055*
H25B	0.2148	0.4717	0.3500	0.055*
H25C	0.3607	0.5358	0.2756	0.055*
C26	0.1261 (2)	0.5688 (2)	0.5249 (2)	0.0355 (6)
H26A	0.1310	0.5911	0.5876	0.053*
H26B	0.0732	0.4958	0.5588	0.053*
H26C	0.0837	0.6274	0.4825	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0307 (8)	0.0283 (9)	0.0448 (9)	0.0079 (7)	−0.0123 (7)	−0.0166 (7)
O2	0.0497 (10)	0.0235 (9)	0.0474 (10)	0.0099 (7)	−0.0223 (8)	−0.0171 (7)
O3	0.0228 (7)	0.0174 (7)	0.0364 (8)	0.0017 (6)	−0.0129 (6)	−0.0105 (6)
O4	0.0246 (8)	0.0212 (8)	0.0471 (9)	0.0035 (6)	−0.0139 (7)	−0.0151 (7)
O5	0.0252 (8)	0.0301 (9)	0.0415 (9)	0.0043 (7)	−0.0074 (7)	−0.0165 (7)
O6	0.0394 (9)	0.0243 (9)	0.0429 (9)	0.0074 (7)	−0.0140 (7)	−0.0184 (7)
O7	0.0257 (8)	0.0195 (8)	0.0348 (8)	−0.0016 (6)	−0.0130 (6)	−0.0089 (6)
O8	0.0308 (8)	0.0185 (8)	0.0308 (8)	0.0028 (6)	−0.0126 (6)	−0.0094 (6)
N1	0.0303 (9)	0.0179 (9)	0.0328 (10)	0.0031 (7)	−0.0125 (8)	−0.0106 (8)
N2	0.0319 (10)	0.0197 (9)	0.0331 (10)	0.0011 (8)	−0.0137 (8)	−0.0096 (8)
N3	0.0234 (9)	0.0187 (9)	0.0354 (10)	0.0032 (7)	−0.0120 (8)	−0.0115 (8)
N4	0.0298 (10)	0.0221 (10)	0.0455 (11)	−0.0031 (8)	−0.0124 (9)	−0.0103 (9)
N5	0.0252 (9)	0.0170 (9)	0.0291 (9)	0.0010 (7)	−0.0101 (7)	−0.0081 (7)
N6	0.0258 (9)	0.0191 (9)	0.0313 (10)	0.0001 (7)	−0.0100 (8)	−0.0083 (8)
N7	0.0241 (9)	0.0186 (9)	0.0309 (9)	0.0018 (7)	−0.0117 (7)	−0.0103 (7)
N8	0.0266 (10)	0.0200 (10)	0.0557 (13)	−0.0013 (8)	−0.0077 (9)	−0.0156 (9)
C1	0.0319 (11)	0.0191 (11)	0.0244 (10)	0.0021 (9)	−0.0134 (9)	−0.0088 (9)
C2	0.0340 (12)	0.0213 (11)	0.0256 (11)	−0.0009 (9)	−0.0134 (9)	−0.0070 (9)
C3	0.0274 (11)	0.0205 (11)	0.0269 (11)	0.0030 (9)	−0.0128 (9)	−0.0096 (9)
C4	0.0264 (11)	0.0188 (11)	0.0325 (11)	0.0003 (8)	−0.0133 (9)	−0.0090 (9)
C5	0.0267 (11)	0.0209 (11)	0.0290 (11)	0.0040 (9)	−0.0116 (9)	−0.0113 (9)
C6	0.0391 (13)	0.0229 (12)	0.0278 (11)	0.0068 (10)	−0.0148 (10)	−0.0116 (9)
C7	0.0344 (13)	0.0409 (15)	0.0446 (14)	0.0137 (11)	−0.0116 (11)	−0.0210 (12)
C8	0.0479 (15)	0.0555 (18)	0.0545 (17)	0.0147 (13)	−0.0253 (13)	−0.0244 (14)
C9	0.0248 (10)	0.0175 (10)	0.0254 (10)	−0.0007 (9)	−0.0097 (9)	−0.0047 (8)
C10	0.0221 (10)	0.0180 (10)	0.0280 (11)	−0.0034 (8)	−0.0092 (8)	−0.0068 (8)
C11	0.0268 (11)	0.0234 (11)	0.0346 (12)	0.0006 (9)	−0.0130 (9)	−0.0077 (9)
C12	0.0285 (11)	0.0338 (13)	0.0294 (11)	−0.0005 (9)	−0.0108 (9)	−0.0118 (10)
C13	0.0295 (11)	0.0211 (11)	0.0305 (11)	0.0025 (9)	−0.0107 (9)	−0.0074 (9)
C14	0.0284 (11)	0.0176 (11)	0.0270 (11)	0.0006 (9)	−0.0122 (9)	−0.0064 (9)
C15	0.0257 (11)	0.0175 (10)	0.0236 (10)	0.0007 (8)	−0.0108 (9)	−0.0055 (8)
C16	0.0284 (11)	0.0180 (10)	0.0237 (10)	0.0017 (8)	−0.0131 (9)	−0.0064 (8)
C17	0.0314 (12)	0.0255 (12)	0.0273 (11)	0.0054 (9)	−0.0125 (9)	−0.0119 (9)
C18	0.0292 (12)	0.0452 (15)	0.0402 (13)	0.0077 (11)	−0.0044 (10)	−0.0234 (12)
C19	0.0383 (14)	0.0593 (18)	0.0593 (17)	0.0192 (13)	−0.0192 (13)	−0.0320 (15)
C20	0.0247 (10)	0.0210 (11)	0.0285 (11)	0.0015 (8)	−0.0103 (9)	−0.0096 (9)
C21	0.0246 (10)	0.0169 (10)	0.0267 (11)	0.0009 (8)	−0.0110 (9)	−0.0065 (8)
C22	0.0276 (11)	0.0186 (10)	0.0225 (10)	−0.0001 (9)	−0.0148 (9)	−0.0027 (8)
C23	0.0323 (11)	0.0185 (11)	0.0330 (11)	−0.0043 (9)	−0.0175 (10)	−0.0054 (9)
C24	0.0380 (12)	0.0220 (12)	0.0354 (12)	−0.0013 (10)	−0.0192 (10)	−0.0033 (10)
C25	0.0477 (14)	0.0295 (13)	0.0372 (13)	−0.0068 (11)	−0.0231 (11)	−0.0075 (10)
C26	0.0305 (12)	0.0313 (13)	0.0441 (13)	−0.0056 (10)	−0.0174 (10)	−0.0073 (11)

Geometric parameters (Å, º) top

O1—C6	1.327 (3)	C7—H7B	0.9700
O1—C7	1.447 (3)	C8—H8D	0.9600
O2—C6	1.202 (3)	C8—H8E	0.9600
O3—C9	1.341 (2)	C8—H8F	0.9600
O3—C10	1.473 (2)	C10—C11	1.507 (3)
O4—C9	1.216 (2)	C10—C13	1.508 (3)
O5—C17	1.328 (2)	C10—C12	1.509 (3)
O5—C18	1.442 (3)	C11—H11A	0.9600
O6—C17	1.198 (3)	C11—H11B	0.9600
O7—C22	1.341 (2)	C11—H11C	0.9600
O7—C23	1.471 (2)	C12—H12A	0.9600
O8—C22	1.216 (2)	C12—H12B	0.9600
N1—C1	1.365 (3)	C12—H12C	0.9600
N1—C6	1.379 (3)	C13—H13A	0.9600
N1—N2	1.390 (2)	C13—H13B	0.9600
N2—C2	1.330 (3)	C13—H13C	0.9600
N3—C9	1.336 (3)	C14—C15	1.430 (3)
N3—C5	1.471 (3)	C15—C16	1.329 (3)
N3—C4	1.472 (2)	C15—C21	1.486 (3)
N4—C2	1.347 (3)	C16—C20	1.484 (3)
N4—H4"	0.8999	C18—C19	1.486 (4)
N4—H4'	0.8999	C18—H18A	0.9700
N5—C16	1.365 (3)	C18—H18B	0.9700
N5—C17	1.373 (3)	C19—H19A	0.9600
N5—N6	1.393 (2)	C19—H19B	0.9600
N6—C14	1.330 (3)	C19—H19C	0.9600
N7—C22	1.339 (3)	C20—H20A	0.9700
N7—C21	1.473 (2)	C20—H20B	0.9700
N7—C20	1.477 (3)	C21—H21A	0.9700
N8—C14	1.338 (3)	C21—H21B	0.9700
N8—H8'	0.8600	C23—C24	1.504 (3)
N8—H8"	0.8600	C23—C26	1.511 (3)
C1—C3	1.329 (3)	C23—C25	1.512 (3)
C1—C5	1.482 (3)	C24—H24A	0.9600
C2—C3	1.429 (3)	C24—H24B	0.9600
C3—C4	1.487 (3)	C24—H24C	0.9600
C4—H4D	0.9700	C25—H25A	0.9600
C4—H4E	0.9700	C25—H25B	0.9600
C5—H5A	0.9700	C25—H25C	0.9600
C5—H5B	0.9700	C26—H26A	0.9600
C7—C8	1.494 (4)	C26—H26B	0.9600
C7—H7A	0.9700	C26—H26C	0.9600

C6—O1—C7	116.59 (18)	C10—C12—H12A	109.5
C9—O3—C10	120.85 (15)	C10—C12—H12B	109.5
C17—O5—C18	117.13 (18)	H12A—C12—H12B	109.5
C22—O7—C23	121.69 (16)	C10—C12—H12C	109.5
C1—N1—C6	128.99 (18)	H12A—C12—H12C	109.5
C1—N1—N2	110.17 (16)	H12B—C12—H12C	109.5
C6—N1—N2	120.78 (17)	C10—C13—H13A	109.5
C2—N2—N1	104.91 (16)	C10—C13—H13B	109.5
C9—N3—C5	124.64 (17)	H13A—C13—H13B	109.5
C9—N3—C4	120.16 (17)	C10—C13—H13C	109.5
C5—N3—C4	114.81 (15)	H13A—C13—H13C	109.5
C2—N4—H4"	121.4	H13B—C13—H13C	109.5
C2—N4—H4'	119.3	N6—C14—N8	122.08 (18)
H4"—N4—H4'	112.9	N6—C14—C15	110.37 (17)
C16—N5—C17	128.92 (17)	N8—C14—C15	127.55 (19)
C16—N5—N6	110.18 (16)	C16—C15—C14	106.07 (18)
C17—N5—N6	120.77 (16)	C16—C15—C21	111.02 (17)
C14—N6—N5	104.90 (16)	C14—C15—C21	142.89 (19)
C22—N7—C21	121.67 (17)	C15—C16—N5	108.47 (17)
C22—N7—C20	123.51 (16)	C15—C16—C20	114.67 (18)
C21—N7—C20	114.55 (15)	N5—C16—C20	136.80 (18)
C14—N8—H8'	120.0	O6—C17—O5	126.8 (2)
C14—N8—H8"	120.0	O6—C17—N5	124.59 (19)
H8'—N8—H8"	120.0	O5—C17—N5	108.57 (17)
C3—C1—N1	108.48 (18)	O5—C18—C19	110.85 (19)
C3—C1—C5	114.49 (19)	O5—C18—H18A	109.5
N1—C1—C5	136.95 (19)	C19—C18—H18A	109.5
N2—C2—N4	121.98 (19)	O5—C18—H18B	109.5
N2—C2—C3	110.42 (18)	C19—C18—H18B	109.5
N4—C2—C3	127.6 (2)	H18A—C18—H18B	108.1
C1—C3—C2	106.00 (19)	C18—C19—H19A	109.5
C1—C3—C4	111.15 (17)	C18—C19—H19B	109.5
C2—C3—C4	142.74 (19)	H19A—C19—H19B	109.5
N3—C4—C3	100.28 (16)	C18—C19—H19C	109.5
N3—C4—H4D	111.7	H19A—C19—H19C	109.5
C3—C4—H4D	111.7	H19B—C19—H19C	109.5
N3—C4—H4E	111.7	N7—C20—C16	98.60 (15)
C3—C4—H4E	111.7	N7—C20—H20A	112.0
H4D—C4—H4E	109.5	C16—C20—H20A	112.0
N3—C5—C1	98.69 (16)	N7—C20—H20B	112.0
N3—C5—H5A	112.0	C16—C20—H20B	112.0
C1—C5—H5A	112.0	H20A—C20—H20B	109.7
N3—C5—H5B	112.0	N7—C21—C15	100.59 (16)
C1—C5—H5B	112.0	N7—C21—H21A	111.7
H5A—C5—H5B	109.7	C15—C21—H21A	111.7
O2—C6—O1	127.0 (2)	N7—C21—H21B	111.7
O2—C6—N1	123.8 (2)	C15—C21—H21B	111.7
O1—C6—N1	109.18 (18)	H21A—C21—H21B	109.4
O1—C7—C8	111.1 (2)	O8—C22—N7	124.23 (18)
O1—C7—H7A	109.4	O8—C22—O7	126.38 (18)
C8—C7—H7A	109.4	N7—C22—O7	109.38 (18)
O1—C7—H7B	109.4	O7—C23—C24	110.13 (16)
C8—C7—H7B	109.4	O7—C23—C26	101.64 (17)
H7A—C7—H7B	108.0	C24—C23—C26	109.97 (18)
C7—C8—H8D	109.5	O7—C23—C25	109.88 (16)
C7—C8—H8E	109.5	C24—C23—C25	112.93 (19)
H8D—C8—H8E	109.5	C26—C23—C25	111.72 (18)
C7—C8—H8F	109.5	C23—C24—H24A	109.5
H8D—C8—H8F	109.5	C23—C24—H24B	109.5
H8E—C8—H8F	109.5	H24A—C24—H24B	109.5
O4—C9—N3	123.50 (18)	C23—C24—H24C	109.5
O4—C9—O3	126.06 (18)	H24A—C24—H24C	109.5
N3—C9—O3	110.43 (18)	H24B—C24—H24C	109.5
O3—C10—C11	102.22 (16)	C23—C25—H25A	109.5
O3—C10—C13	108.64 (16)	C23—C25—H25B	109.5
C11—C10—C13	111.19 (16)	H25A—C25—H25B	109.5
O3—C10—C12	111.02 (15)	C23—C25—H25C	109.5
C11—C10—C12	110.14 (18)	H25A—C25—H25C	109.5
C13—C10—C12	113.09 (18)	H25B—C25—H25C	109.5
C10—C11—H11A	109.5	C23—C26—H26A	109.5
C10—C11—H11B	109.5	C23—C26—H26B	109.5
H11A—C11—H11B	109.5	H26A—C26—H26B	109.5
C10—C11—H11C	109.5	C23—C26—H26C	109.5
H11A—C11—H11C	109.5	H26A—C26—H26C	109.5
H11B—C11—H11C	109.5	H26B—C26—H26C	109.5

C1—N1—N2—C2	−0.5 (2)	C9—O3—C10—C13	−67.0 (2)
C6—N1—N2—C2	−178.02 (18)	C9—O3—C10—C12	58.0 (2)
C16—N5—N6—C14	−0.5 (2)	N5—N6—C14—N8	−179.34 (19)
C17—N5—N6—C14	−176.67 (18)	N5—N6—C14—C15	0.6 (2)
C6—N1—C1—C3	177.6 (2)	N6—C14—C15—C16	−0.5 (2)
N2—N1—C1—C3	0.4 (2)	N8—C14—C15—C16	179.4 (2)
C6—N1—C1—C5	−5.9 (4)	N6—C14—C15—C21	−179.0 (3)
N2—N1—C1—C5	176.8 (2)	N8—C14—C15—C21	0.9 (4)
N1—N2—C2—N4	178.65 (18)	C14—C15—C16—N5	0.2 (2)
N1—N2—C2—C3	0.4 (2)	C21—C15—C16—N5	179.20 (16)
N1—C1—C3—C2	−0.1 (2)	C14—C15—C16—C20	−177.62 (17)
C5—C1—C3—C2	−177.45 (17)	C21—C15—C16—C20	1.4 (3)
N1—C1—C3—C4	177.00 (17)	C17—N5—C16—C15	175.96 (19)
C5—C1—C3—C4	−0.4 (3)	N6—N5—C16—C15	0.2 (2)
N2—C2—C3—C1	−0.2 (2)	C17—N5—C16—C20	−7.0 (4)
N4—C2—C3—C1	−178.3 (2)	N6—N5—C16—C20	177.3 (2)
N2—C2—C3—C4	−175.7 (3)	C18—O5—C17—O6	0.6 (3)
N4—C2—C3—C4	6.1 (4)	C18—O5—C17—N5	−179.03 (17)
C9—N3—C4—C3	−165.54 (18)	C16—N5—C17—O6	−180.0 (2)
C5—N3—C4—C3	7.5 (2)	N6—N5—C17—O6	−4.6 (3)
C1—C3—C4—N3	−4.2 (2)	C16—N5—C17—O5	−0.4 (3)
C2—C3—C4—N3	171.2 (3)	N6—N5—C17—O5	175.03 (16)
C9—N3—C5—C1	165.14 (19)	C17—O5—C18—C19	86.1 (3)
C4—N3—C5—C1	−7.6 (2)	C22—N7—C20—C16	−166.46 (18)
C3—C1—C5—N3	4.7 (2)	C21—N7—C20—C16	7.7 (2)
N1—C1—C5—N3	−171.7 (2)	C15—C16—C20—N7	−5.4 (2)
C7—O1—C6—O2	4.9 (3)	N5—C16—C20—N7	177.7 (2)
C7—O1—C6—N1	−174.19 (18)	C22—N7—C21—C15	167.14 (18)
C1—N1—C6—O2	−178.0 (2)	C20—N7—C21—C15	−7.1 (2)
N2—N1—C6—O2	−0.9 (3)	C16—C15—C21—N7	3.3 (2)
C1—N1—C6—O1	1.1 (3)	C14—C15—C21—N7	−178.2 (3)
N2—N1—C6—O1	178.17 (16)	C21—N7—C22—O8	−0.6 (3)
C6—O1—C7—C8	−86.4 (2)	C20—N7—C22—O8	173.13 (19)
C5—N3—C9—O4	179.44 (19)	C21—N7—C22—O7	−179.94 (16)
C4—N3—C9—O4	−8.2 (3)	C20—N7—C22—O7	−6.2 (3)
C5—N3—C9—O3	−2.0 (3)	C23—O7—C22—O8	12.3 (3)
C4—N3—C9—O3	170.39 (16)	C23—O7—C22—N7	−168.41 (16)
C10—O3—C9—O4	−3.2 (3)	C22—O7—C23—C24	55.5 (2)
C10—O3—C9—N3	178.21 (16)	C22—O7—C23—C26	172.01 (17)
C9—O3—C10—C11	175.42 (17)	C22—O7—C23—C25	−69.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8"···O4ⁱ	0.86	2.25	3.069 (3)	160
N8—H8′···N2ⁱⁱ	0.86	2.26	3.087 (3)	163
N4—H4′···N6ⁱⁱⁱ	0.90	2.25	3.104 (3)	157
N4—H4"···O8^iv	0.90	2.36	3.233 (3)	163

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

Experimental details

Crystal data
Chemical formula	C₁₃H₂₀N₄O₄
M_r	296.33
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	10.772 (3), 12.180 (4), 12.986 (4)
α, β, γ (°)	70.845 (5), 65.875 (4), 85.821 (5)
V (Å³)	1465.2 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.06 × 0.05 × 0.04

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.994, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	7444, 5102, 3915
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.128, 1.03
No. of reflections	5102
No. of parameters	387
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.32

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), 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
N8—H8"···O4ⁱ	0.86	2.25	3.069 (3)	160
N8—H8'···N2ⁱⁱ	0.86	2.26	3.087 (3)	163
N4—H4'···N6ⁱⁱⁱ	0.90	2.25	3.104 (3)	157
N4—H4"···O8^iv	0.90	2.36	3.233 (3)	163

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

Acknowledgements

This work was supported by the National Natural Science Foundation (81072577).

References

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fancelli, D., et al. (2005). J. Med. Chem. 48, 3080–3084. Web of Science CrossRef PubMed CAS Google Scholar
Gadekar, S. M., Johnson, B. D. & Cohen, E. (1968). J. Med. Chem. 11, 616–618. CrossRef CAS PubMed Web of Science Google Scholar
Guo, X., Bai, X. G., Li, Y. L. & Wang, Y. C. (2010). Acta Cryst. E66, o1108. 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

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

5-tert-Butyl 1-ethyl 3-amino-1,4,5,6-tetra­hydro­pyrrolo­[3,4-c]pyrazole-1,5-di­carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

5-tert-Butyl 1-ethyl 3-amino-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole-1,5-dicarboxylate