4-(4-Bromo­phen­yl)-4,5,6,7-tetra­hydro-3-methyl-6-oxo-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile ethanol solvate

Fan, X.-S.; Li, X.-Y.; Wang, X.; Li, D.-F.; Zhang, X.-Y.

doi:10.1107/S1600536808028638

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1925

doi:10.1107/S1600536808028638

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4-(4-Bromophenyl)-4,5,6,7-tetrahydro-3-methyl-6-oxo-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile ethanol solvate

Xue-Sen Fan,^a ^* Xiao-Yan Li,^a Xia Wang,^a Dong-Fang Li ^a and Xin-Ying Zhang ^a

^aSchool of Chemistry and Environmental Sciences, Henan Key Laboratory for Environmental Pollution Control, Henan Normal University, Xinxiang, Henan 453007, People's Republic of China
^*Correspondence e-mail: xuesen.fan@yahoo.com

(Received 1 September 2008; accepted 7 September 2008; online 13 September 2008)

In the structure of the title compound, C₂₀H₁₅BrN₄O·C₂H₆O, the hydrogenated pyridinone ring adopts an envelope conformation. The dihedral angle between the bromo-substituted phenyl ring and the pyrazole ring is 79.6 (1)°, and that between the non-substituted phenyl ring and the pyrazole ring is 51.2 (1)°. In the crystal structure, molecules are linked via intermolecular N—H⋯O and O—H⋯N hydrogen bonds. A short intermolecular N⋯Br contact [3.213 (4) Å] is present in the crystal structure.

Related literature

For general background, see: Falcó et al. (2005 ); Kung & Wager (2007 ).

Experimental

Crystal data

C₂₀H₁₅BrN₄O·C₂H₆O
M_r = 453.34
Monoclinic, P 2₁ /c
a = 21.871 (9) Å
b = 9.209 (4) Å
c = 10.552 (5) Å
β = 90.370 (5)°
V = 2125.4 (15) Å³
Z = 4
Mo Kα radiation
μ = 1.96 mm⁻¹
T = 295 (2) K
0.31 × 0.24 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.586, T_max = 0.770
10428 measured reflections
3947 independent reflections
2414 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.121
S = 1.01
3947 reflections
265 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1ⁱ	0.82	2.06	2.874 (4)	171
N3—H3D⋯O2	0.97	1.84	2.786 (3)	166
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808028638/xu2452sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808028638/xu2452Isup2.hkl

checkCIF report

Comment top

Pyrazolo[3,4-b]pyridine-6-ones as a subunit of pyrazolo[3,4-b]pyridine acted as potential hypnotic drugs in many cases (Falcó et al., 2005). Hydrogenated pyrazolo[3,4-b]pyridin-6-ones have been found with good biological activity such as GSK-3 inhibitors (Kung et al., 2007) and have the potential to be used as novel building blocks to construct new nitrogen-containing molecules. The title compound is one of the hydrogenated pyrazolo[3,4-b]pyridin-6-one derivatives. Its crystal structure is presented here.

In the title compound (Fig. 1) there are four rings, three planar rings and one nonplanar hydrogenated pyridinone ring. The hydrogenated pyridinone ring is fused to the pyrazole ring and adopts an envelope conformation with C4 at flap position. The dihedral angle between the bromo-substituted benzene ring and the pyrazole ring is 79.6 (1)° and that between the non-substituted phenyl ring and the pyrazole ring is 51.2 (1)°.

Intermolecular N—H···O and O—H···N hydrogen bonding (Table 1) and the weak intermolecular Br1···N4ⁱ contact present in the crystal structure [symmetry code: (i) 1-x, -1/2+y, 1/2-z].

Related literature top

For general background, see: Falcó et al. (2005); Kung et al. (2007).

Experimental top

4-Bromobenzaldehyde (1 mmol) and ethyl cyanoacetate (1 mmol) were added to 1 ml of 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim][BF₄]). The mixture was stirred at 353 K until the disappearance of bromobenzaldehyde. Upon cooling to room temperature, 5-amino-3-methyl-1-phenylpyrazole (1 mmol) was added and the mixture was stirred at room temperature for a certain period of time to complete the reaction (monitored by TLC). The reaction time was 9 h totally. Upon completion, the product was not separated from the reaction system; instead, 4 ml of ethanol was added. Single crystals of the title compound were obtained by slow evaporation of the solvent.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997)'; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. Dashed line indicates hydrogen bonding.

4-(4-Bromophenyl)-4,5,6,7-tetrahydro-3-methyl-6-oxo-1-phenyl-1H- pyrazolo[3,4-b]pyridine-5-carbonitrile ethanol solvate top

Crystal data top

C₂₀H₁₅BrN₄O·C₂H₆O	F(000) = 928
M_r = 453.34	D_x = 1.417 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2154 reflections
a = 21.871 (9) Å	θ = 2.4–22.3°
b = 9.209 (4) Å	µ = 1.96 mm⁻¹
c = 10.552 (5) Å	T = 295 K
β = 90.370 (5)°	Block, colourless
V = 2125.4 (15) Å³	0.31 × 0.24 × 0.14 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3947 independent reflections
Radiation source: fine-focus sealed tube	2414 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −26→26
T_min = 0.586, T_max = 0.770	k = −11→9
10428 measured reflections	l = −12→12

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0415P)² + 1.3425P] where P = (F_o² + 2F_c²)/3
3947 reflections	(Δ/σ)_max = 0.001
265 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

C₂₀H₁₅BrN₄O·C₂H₆O	V = 2125.4 (15) Å³
M_r = 453.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 21.871 (9) Å	µ = 1.96 mm⁻¹
b = 9.209 (4) Å	T = 295 K
c = 10.552 (5) Å	0.31 × 0.24 × 0.14 mm
β = 90.370 (5)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3947 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	2414 reflections with I > 2σ(I)
T_min = 0.586, T_max = 0.770	R_int = 0.035
10428 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.01	Δρ_max = 0.53 e Å⁻³
3947 reflections	Δρ_min = −0.51 e Å⁻³
265 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
Br1	0.449857 (19)	0.58567 (7)	0.18723 (5)	0.1023 (3)
O1	0.77687 (11)	0.8095 (2)	0.2363 (2)	0.0553 (6)
O2	0.83439 (11)	0.5202 (3)	0.0508 (2)	0.0558 (6)
H2	0.8220	0.4430	0.0218	0.084*
N1	0.77906 (13)	0.2474 (3)	0.4696 (2)	0.0478 (7)
N2	0.80852 (12)	0.3344 (3)	0.3832 (2)	0.0431 (6)
N3	0.79796 (12)	0.5800 (3)	0.2978 (2)	0.0434 (6)
H3D	0.8174	0.5606	0.2174	0.065*
N4	0.67632 (15)	0.9759 (4)	0.4375 (3)	0.0732 (9)
C1	0.73512 (15)	0.3303 (4)	0.5195 (3)	0.0442 (8)
C2	0.73547 (14)	0.4703 (3)	0.4646 (3)	0.0404 (7)
C3	0.69597 (14)	0.6023 (3)	0.4808 (3)	0.0414 (8)
H3	0.6870	0.6128	0.5712	0.050*
C4	0.73741 (14)	0.7328 (3)	0.4401 (3)	0.0407 (8)
H4	0.7688	0.7432	0.5061	0.049*
C5	0.77157 (14)	0.7129 (4)	0.3138 (3)	0.0418 (8)
C6	0.78163 (14)	0.4672 (3)	0.3795 (3)	0.0387 (7)
C7	0.70350 (16)	0.8703 (4)	0.4370 (3)	0.0487 (8)
C8	0.69393 (18)	0.2752 (4)	0.6197 (3)	0.0648 (10)
H8A	0.6546	0.2537	0.5833	0.097*
H8B	0.6895	0.3477	0.6843	0.097*
H8C	0.7110	0.1886	0.6561	0.097*
C9	0.63578 (14)	0.5971 (3)	0.4089 (3)	0.0426 (8)
C10	0.58214 (16)	0.6426 (4)	0.4648 (3)	0.0628 (10)
H10	0.5830	0.6750	0.5482	0.075*
C11	0.52737 (17)	0.6412 (5)	0.3997 (4)	0.0771 (13)
H11	0.4918	0.6721	0.4391	0.092*
C12	0.52561 (16)	0.5939 (4)	0.2764 (4)	0.0626 (10)
C13	0.57776 (16)	0.5502 (4)	0.2179 (3)	0.0661 (11)
H13	0.5765	0.5189	0.1341	0.079*
C14	0.63241 (16)	0.5528 (4)	0.2835 (3)	0.0586 (10)
H14	0.6680	0.5240	0.2427	0.070*
C15	0.85626 (15)	0.2756 (4)	0.3081 (3)	0.0456 (8)
C16	0.84675 (18)	0.1459 (4)	0.2460 (3)	0.0559 (9)
H16	0.8097	0.0969	0.2529	0.067*
C17	0.8936 (2)	0.0902 (5)	0.1732 (4)	0.0769 (13)
H17	0.8880	0.0026	0.1309	0.092*
C18	0.9477 (2)	0.1616 (6)	0.1624 (4)	0.0854 (14)
H18	0.9786	0.1231	0.1125	0.103*
C19	0.95680 (19)	0.2899 (6)	0.2249 (4)	0.0816 (13)
H19	0.9939	0.3384	0.2175	0.098*
C20	0.91114 (17)	0.3477 (4)	0.2990 (4)	0.0627 (10)
H20	0.9174	0.4344	0.3423	0.075*
C21	0.89214 (19)	0.5522 (5)	−0.0008 (4)	0.0750 (12)
H21A	0.8879	0.5692	−0.0911	0.090*
H21B	0.9192	0.4699	0.0114	0.090*
C22	0.9183 (3)	0.6785 (6)	0.0587 (6)	0.128 (2)
H22A	0.8972	0.7637	0.0298	0.192*
H22B	0.9607	0.6855	0.0371	0.192*
H22C	0.9144	0.6704	0.1490	0.192*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0484 (3)	0.1630 (6)	0.0952 (4)	0.0022 (3)	−0.0134 (2)	−0.0219 (3)
O1	0.0811 (17)	0.0401 (14)	0.0446 (13)	−0.0010 (13)	0.0004 (11)	0.0073 (11)
O2	0.0628 (16)	0.0541 (16)	0.0508 (13)	−0.0062 (13)	0.0098 (11)	−0.0147 (12)
N1	0.0548 (17)	0.0385 (16)	0.0503 (16)	−0.0019 (14)	0.0086 (13)	0.0083 (13)
N2	0.0485 (16)	0.0365 (16)	0.0444 (14)	0.0022 (14)	0.0089 (12)	0.0029 (13)
N3	0.0540 (16)	0.0375 (16)	0.0387 (14)	0.0027 (13)	0.0093 (12)	0.0032 (12)
N4	0.065 (2)	0.049 (2)	0.105 (3)	0.0064 (18)	−0.0053 (18)	−0.0055 (19)
C1	0.0478 (19)	0.039 (2)	0.0458 (18)	−0.0049 (17)	0.0068 (15)	0.0041 (16)
C2	0.0456 (18)	0.039 (2)	0.0366 (16)	0.0001 (16)	0.0007 (14)	0.0015 (14)
C3	0.0476 (18)	0.042 (2)	0.0344 (15)	−0.0009 (16)	0.0043 (13)	−0.0030 (14)
C4	0.0491 (18)	0.0367 (19)	0.0364 (16)	0.0024 (16)	−0.0051 (14)	−0.0046 (14)
C5	0.0486 (19)	0.040 (2)	0.0371 (16)	−0.0037 (16)	−0.0039 (14)	0.0000 (16)
C6	0.0447 (18)	0.0332 (19)	0.0383 (16)	0.0012 (15)	0.0017 (14)	0.0015 (14)
C7	0.052 (2)	0.040 (2)	0.054 (2)	−0.0029 (18)	−0.0030 (16)	−0.0052 (16)
C8	0.074 (3)	0.053 (2)	0.068 (2)	−0.001 (2)	0.024 (2)	0.0119 (19)
C9	0.0445 (18)	0.0367 (19)	0.0466 (18)	0.0004 (15)	0.0051 (14)	−0.0050 (15)
C10	0.055 (2)	0.084 (3)	0.049 (2)	−0.001 (2)	0.0105 (17)	−0.0201 (19)
C11	0.043 (2)	0.117 (4)	0.072 (3)	0.004 (2)	0.0126 (19)	−0.022 (3)
C12	0.043 (2)	0.075 (3)	0.069 (2)	−0.001 (2)	−0.0050 (18)	−0.009 (2)
C13	0.054 (2)	0.087 (3)	0.057 (2)	0.005 (2)	−0.0018 (18)	−0.025 (2)
C14	0.047 (2)	0.073 (3)	0.056 (2)	0.0102 (19)	0.0020 (16)	−0.0236 (19)
C15	0.050 (2)	0.043 (2)	0.0433 (17)	0.0105 (17)	0.0019 (15)	0.0024 (16)
C16	0.071 (2)	0.046 (2)	0.051 (2)	0.0061 (19)	0.0051 (18)	−0.0011 (17)
C17	0.119 (4)	0.052 (3)	0.060 (2)	0.021 (3)	0.017 (2)	−0.004 (2)
C18	0.091 (4)	0.086 (4)	0.080 (3)	0.038 (3)	0.034 (3)	0.012 (3)
C19	0.054 (3)	0.093 (4)	0.098 (3)	0.008 (3)	0.017 (2)	0.007 (3)
C20	0.054 (2)	0.062 (3)	0.072 (2)	0.002 (2)	0.0058 (19)	−0.001 (2)
C21	0.071 (3)	0.079 (3)	0.075 (3)	−0.010 (2)	0.016 (2)	−0.015 (2)
C22	0.105 (4)	0.127 (5)	0.152 (5)	−0.062 (4)	0.036 (4)	−0.049 (4)

Geometric parameters (Å, º) top

Br1—C12	1.901 (4)	C9—C14	1.386 (4)
O1—C5	1.215 (3)	C10—C11	1.377 (5)
O2—C21	1.409 (4)	C10—H10	0.9300
O2—H2	0.8200	C11—C12	1.373 (5)
N1—C1	1.338 (4)	C11—H11	0.9300
N1—N2	1.377 (3)	C12—C13	1.361 (5)
N2—C6	1.357 (4)	C13—C14	1.378 (5)
N2—C15	1.422 (4)	C13—H13	0.9300
N3—C5	1.364 (4)	C14—H14	0.9300
N3—C6	1.398 (4)	C15—C20	1.376 (5)
N3—H3D	0.9687	C15—C16	1.377 (5)
N4—C7	1.140 (4)	C16—C17	1.383 (5)
C1—C2	1.414 (4)	C16—H16	0.9300
C1—C8	1.482 (4)	C17—C18	1.359 (6)
C2—C6	1.356 (4)	C17—H17	0.9300
C2—C3	1.502 (4)	C18—C19	1.367 (6)
C3—C9	1.516 (4)	C18—H18	0.9300
C3—C4	1.567 (4)	C19—C20	1.379 (5)
C3—H3	0.9800	C19—H19	0.9300
C4—C7	1.468 (5)	C20—H20	0.9300
C4—C5	1.544 (4)	C21—C22	1.438 (6)
C4—H4	0.9800	C21—H21A	0.9700
C8—H8A	0.9600	C21—H21B	0.9700
C8—H8B	0.9600	C22—H22A	0.9600
C8—H8C	0.9600	C22—H22B	0.9600
C9—C10	1.381 (5)	C22—H22C	0.9600

C21—O2—H2	109.5	C9—C10—H10	119.2
C1—N1—N2	105.7 (2)	C12—C11—C10	119.6 (3)
C6—N2—N1	109.8 (2)	C12—C11—H11	120.2
C6—N2—C15	130.3 (3)	C10—C11—H11	120.2
N1—N2—C15	119.7 (3)	C13—C12—C11	120.4 (3)
C5—N3—C6	118.8 (3)	C13—C12—Br1	119.6 (3)
C5—N3—H3D	117.5	C11—C12—Br1	120.0 (3)
C6—N3—H3D	121.2	C12—C13—C14	119.6 (3)
N1—C1—C2	110.6 (3)	C12—C13—H13	120.2
N1—C1—C8	121.8 (3)	C14—C13—H13	120.2
C2—C1—C8	127.5 (3)	C13—C14—C9	121.7 (3)
C6—C2—C1	105.0 (3)	C13—C14—H14	119.1
C6—C2—C3	121.6 (3)	C9—C14—H14	119.1
C1—C2—C3	133.4 (3)	C20—C15—C16	121.0 (3)
C2—C3—C9	114.6 (3)	C20—C15—N2	120.0 (3)
C2—C3—C4	104.8 (2)	C16—C15—N2	119.1 (3)
C9—C3—C4	112.9 (2)	C15—C16—C17	118.4 (4)
C2—C3—H3	108.1	C15—C16—H16	120.8
C9—C3—H3	108.1	C17—C16—H16	120.8
C4—C3—H3	108.1	C18—C17—C16	121.0 (4)
C7—C4—C5	109.3 (3)	C18—C17—H17	119.5
C7—C4—C3	112.0 (3)	C16—C17—H17	119.5
C5—C4—C3	115.4 (2)	C17—C18—C19	120.1 (4)
C7—C4—H4	106.5	C17—C18—H18	119.9
C5—C4—H4	106.5	C19—C18—H18	119.9
C3—C4—H4	106.5	C18—C19—C20	120.2 (4)
O1—C5—N3	122.1 (3)	C18—C19—H19	119.9
O1—C5—C4	122.9 (3)	C20—C19—H19	119.9
N3—C5—C4	114.9 (3)	C15—C20—C19	119.3 (4)
C2—C6—N2	108.9 (3)	C15—C20—H20	120.4
C2—C6—N3	125.9 (3)	C19—C20—H20	120.4
N2—C6—N3	125.1 (3)	O2—C21—C22	110.8 (3)
N4—C7—C4	178.1 (4)	O2—C21—H21A	109.5
C1—C8—H8A	109.5	C22—C21—H21A	109.5
C1—C8—H8B	109.5	O2—C21—H21B	109.5
H8A—C8—H8B	109.5	C22—C21—H21B	109.5
C1—C8—H8C	109.5	H21A—C21—H21B	108.1
H8A—C8—H8C	109.5	C21—C22—H22A	109.5
H8B—C8—H8C	109.5	C21—C22—H22B	109.5
C10—C9—C14	117.1 (3)	H22A—C22—H22B	109.5
C10—C9—C3	121.0 (3)	C21—C22—H22C	109.5
C14—C9—C3	121.8 (3)	H22A—C22—H22C	109.5
C11—C10—C9	121.6 (3)	H22B—C22—H22C	109.5
C11—C10—H10	119.2

C1—N1—N2—C6	−1.3 (3)	C5—N3—C6—C2	9.3 (4)
C1—N1—N2—C15	−176.8 (3)	C5—N3—C6—N2	−172.9 (3)
N2—N1—C1—C2	0.7 (3)	C5—C4—C7—N4	168 (11)
N2—N1—C1—C8	−178.6 (3)	C3—C4—C7—N4	39 (12)
N1—C1—C2—C6	0.0 (3)	C2—C3—C9—C10	137.1 (3)
C8—C1—C2—C6	179.4 (3)	C4—C3—C9—C10	−103.1 (4)
N1—C1—C2—C3	177.5 (3)	C2—C3—C9—C14	−45.7 (4)
C8—C1—C2—C3	−3.1 (6)	C4—C3—C9—C14	74.2 (4)
C6—C2—C3—C9	97.3 (3)	C14—C9—C10—C11	1.3 (6)
C1—C2—C3—C9	−79.9 (4)	C3—C9—C10—C11	178.7 (4)
C6—C2—C3—C4	−27.0 (4)	C9—C10—C11—C12	−0.1 (7)
C1—C2—C3—C4	155.8 (3)	C10—C11—C12—C13	−0.8 (7)
C2—C3—C4—C7	173.7 (2)	C10—C11—C12—Br1	178.0 (3)
C9—C3—C4—C7	48.4 (3)	C11—C12—C13—C14	0.5 (6)
C2—C3—C4—C5	47.8 (3)	Br1—C12—C13—C14	−178.4 (3)
C9—C3—C4—C5	−77.5 (3)	C12—C13—C14—C9	0.8 (6)
C6—N3—C5—O1	−169.4 (3)	C10—C9—C14—C13	−1.7 (6)
C6—N3—C5—C4	13.4 (4)	C3—C9—C14—C13	−179.0 (3)
C7—C4—C5—O1	11.5 (4)	C6—N2—C15—C20	54.7 (5)
C3—C4—C5—O1	138.8 (3)	N1—N2—C15—C20	−130.8 (3)
C7—C4—C5—N3	−171.3 (3)	C6—N2—C15—C16	−125.7 (4)
C3—C4—C5—N3	−44.0 (4)	N1—N2—C15—C16	48.7 (4)
C1—C2—C6—N2	−0.8 (3)	C20—C15—C16—C17	−0.6 (5)
C3—C2—C6—N2	−178.7 (3)	N2—C15—C16—C17	179.9 (3)
C1—C2—C6—N3	177.2 (3)	C15—C16—C17—C18	−0.2 (6)
C3—C2—C6—N3	−0.6 (5)	C16—C17—C18—C19	0.6 (7)
N1—N2—C6—C2	1.3 (3)	C17—C18—C19—C20	−0.1 (7)
C15—N2—C6—C2	176.2 (3)	C16—C15—C20—C19	1.0 (5)
N1—N2—C6—N3	−176.7 (3)	N2—C15—C20—C19	−179.5 (3)
C15—N2—C6—N3	−1.8 (5)	C18—C19—C20—C15	−0.7 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1ⁱ	0.82	2.06	2.874 (4)	171
N3—H3D···O2	0.97	1.84	2.786 (3)	166

Symmetry code: (i) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₅BrN₄O·C₂H₆O
M_r	453.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	21.871 (9), 9.209 (4), 10.552 (5)
β (°)	90.370 (5)
V (Å³)	2125.4 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.96
Crystal size (mm)	0.31 × 0.24 × 0.14

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.586, 0.770
No. of measured, independent and observed [I > 2σ(I)] reflections	10428, 3947, 2414
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.121, 1.01
No. of reflections	3947
No. of parameters	265
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.51

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997)', SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1ⁱ	0.82	2.06	2.874 (4)	170.6
N3—H3D···O2	0.97	1.84	2.786 (3)	165.6

Symmetry code: (i) x, −y+1/2, z−1/2.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 20772025) and the Program for Science and Technology Innovation Talents in Universities of Henan Province (No. 2008HASTIT006).

References

Bruker (1997). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Falcó, J. L., Lloveras, M., Buira, I., Teixidó, J., Borrell, J. I., Méndez, E., Terencio, J., Palomer, A. & Guglietta, A. (2005). Eur. J. Med. Chem. 40, 1179–1187. Web of Science PubMed Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Kung, D. W. & Wager, T. T. (2007). US Patent 7 300 944. 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 64| Part 10| October 2008| Page o1925

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

4-(4-Bromo­phen­yl)-4,5,6,7-tetra­hydro-3-methyl-6-oxo-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbo­nitrile ethanol solvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-(4-Bromophenyl)-4,5,6,7-tetrahydro-3-methyl-6-oxo-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile ethanol solvate