Benzyl 5-phenyl-pyrazolo-[5,1-a]isoquino-line-1-carboxyl-ate.

In the title compound, C(25)H(18)N(2)O(2), the pyrazolo-[5,1-a]iso-quin-oline ring system is approximately planar [maximum deviation = 0.027 (2) Å] and is oriented at dihedral angles of 57.22 (6) and 71.36 (7)° with respect to the two phenyl rings. The phenyl rings are twisted to each other by a dihedral angle of 66.33 (8)°. A weak intra-molecular C-H⋯O hydrogen bond occurs. In the crystal, weak C-H⋯π inter-actions are present.

Related literature

For the biological activity of fused isoquinoline compounds, see: Aubry et al. (2004 ▶); Marco et al. (2005 ▶); Reddy et al. (1999 ▶). For related structures, see: Chen & Wu (2010 ▶); Ye et al. (2010 ▶); Yu et al. (2011a ▶,b ▶). For selected examples of multi-component reactions, see: Dömling & Ugi (2000 ▶); Nair et al. (2003 ▶); Ramon & Yus (2005 ▶).

Experimental

Crystal data

C25H18N2O2

M = 378.41

Monoclinic,

a = 9.161 (3) Å

b = 18.397 (6) Å

c = 11.621 (4) Å

β = 98.132 (6)°

V = 1938.9 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 173 K

0.22 × 0.15 × 0.11 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

9583 measured reflections

3378 independent reflections

1852 reflections with I > 2σ(I)

R int = 0.098

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.116

S = 0.87

3378 reflections

263 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.24 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536811050586/xu5395sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050586/xu5395Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C25H18N2O2	F(000) = 792
Mr = 378.41	Dx = 1.296 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3378 reflections
a = 9.161 (3) Å	θ = 2.1–25.0°
b = 18.397 (6) Å	µ = 0.08 mm−1
c = 11.621 (4) Å	T = 173 K
β = 98.132 (6)°	Block, colorless
V = 1938.9 (12) Å3	0.22 × 0.15 × 0.11 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	1852 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.098
graphite	θmax = 25.0°, θmin = 2.1°
Detector resolution: 10 pixels mm-1	h = −9→10
ω scans	k = −20→21
9583 measured reflections	l = −13→13
3378 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050	H-atom parameters constrained
wR(F2) = 0.116	w = 1/[σ2(Fo2) + (0.P)2] where P = (Fo2 + 2Fc2)/3
S = 0.87	(Δ/σ)max < 0.001
3378 reflections	Δρmax = 0.18 e Å−3
263 parameters	Δρmin = −0.24 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0076 (11)

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.

	x	y	z	Uiso*/Ueq
N1	0.4210 (2)	0.36318 (10)	0.06266 (15)	0.0314 (5)
N2	0.2711 (2)	0.36122 (10)	0.01947 (16)	0.0355 (5)
O1	0.41215 (19)	0.59556 (8)	0.15872 (15)	0.0450 (5)
O2	0.17077 (19)	0.56806 (8)	0.10441 (14)	0.0401 (5)
C1	0.3320 (3)	0.16526 (14)	−0.1618 (2)	0.0455 (7)
H1A	0.2871	0.1641	−0.2407	0.055*
C2	0.3482 (3)	0.10140 (14)	−0.0978 (2)	0.0486 (7)
H2B	0.3152	0.0567	−0.1332	0.058*
C3	0.4124 (3)	0.10268 (13)	0.0176 (2)	0.0476 (7)
H3A	0.4236	0.0589	0.0612	0.057*
C4	0.4604 (3)	0.16836 (12)	0.0697 (2)	0.0405 (7)
H4A	0.5029	0.1693	0.1491	0.049*
C5	0.4462 (3)	0.23300 (12)	0.0054 (2)	0.0339 (6)
C6	0.3809 (3)	0.23078 (13)	−0.1113 (2)	0.0414 (7)
H6A	0.3701	0.2743	−0.1557	0.050*
C7	0.5104 (3)	0.30141 (12)	0.06079 (19)	0.0335 (6)
C8	0.6539 (3)	0.30793 (12)	0.1091 (2)	0.0387 (6)
H8A	0.7168	0.2669	0.1095	0.046*
C9	0.7137 (3)	0.37483 (13)	0.1595 (2)	0.0359 (6)
C10	0.6211 (3)	0.43691 (12)	0.16259 (19)	0.0320 (6)
C11	0.4672 (3)	0.43004 (12)	0.11022 (19)	0.0298 (6)
C12	0.8650 (3)	0.38081 (14)	0.2056 (2)	0.0468 (7)
H12A	0.9282	0.3402	0.2021	0.056*
C13	0.9217 (3)	0.44468 (14)	0.2553 (2)	0.0496 (7)
H13A	1.0236	0.4480	0.2851	0.059*
C14	0.8296 (3)	0.50468 (14)	0.2621 (2)	0.0463 (7)
H14A	0.8684	0.5480	0.2992	0.056*
C15	0.6817 (3)	0.50136 (12)	0.2150 (2)	0.0384 (7)
H15A	0.6208	0.5429	0.2180	0.046*
C16	0.3387 (3)	0.47398 (12)	0.09507 (19)	0.0308 (6)
C17	0.2256 (3)	0.42822 (12)	0.0405 (2)	0.0363 (6)
H17A	0.1263	0.4437	0.0207	0.044*
C18	0.3186 (3)	0.55095 (13)	0.1236 (2)	0.0352 (6)
C19	0.1330 (3)	0.64296 (12)	0.1286 (2)	0.0403 (7)
H19A	0.0503	0.6591	0.0700	0.048*
H19B	0.2187	0.6747	0.1218	0.048*
C20	0.0897 (3)	0.65106 (12)	0.2487 (2)	0.0366 (6)
C21	−0.0315 (3)	0.69401 (12)	0.2649 (2)	0.0462 (7)
H21A	−0.0878	0.7166	0.1998	0.055*
C22	−0.0709 (3)	0.70417 (14)	0.3754 (3)	0.0585 (9)
H22A	−0.1525	0.7343	0.3851	0.070*
C23	0.0080 (4)	0.67062 (15)	0.4707 (3)	0.0622 (9)
H23A	−0.0197	0.6773	0.5457	0.075*
C24	0.1283 (3)	0.62686 (15)	0.4565 (2)	0.0548 (8)
H24A	0.1831	0.6037	0.5219	0.066*
C25	0.1679 (3)	0.61719 (13)	0.3465 (2)	0.0434 (7)
H25A	0.2496	0.5870	0.3374	0.052*

	U11	U22	U33	U12	U13	U23
N1	0.0286 (13)	0.0336 (11)	0.0314 (12)	−0.0006 (10)	0.0014 (9)	−0.0017 (9)
N2	0.0279 (13)	0.0405 (12)	0.0365 (12)	0.0008 (11)	−0.0010 (9)	0.0006 (9)
O1	0.0367 (12)	0.0391 (10)	0.0573 (12)	−0.0019 (9)	0.0002 (9)	−0.0078 (8)
O2	0.0341 (11)	0.0390 (10)	0.0454 (11)	0.0070 (9)	−0.0014 (8)	−0.0059 (8)
C1	0.0453 (19)	0.0571 (17)	0.0327 (16)	0.0032 (15)	0.0011 (13)	−0.0113 (13)
C2	0.0451 (19)	0.0430 (16)	0.056 (2)	−0.0034 (14)	0.0031 (15)	−0.0117 (14)
C3	0.050 (2)	0.0409 (16)	0.0511 (19)	0.0027 (14)	0.0032 (15)	0.0019 (13)
C4	0.0387 (17)	0.0444 (15)	0.0364 (15)	0.0014 (14)	−0.0012 (12)	−0.0027 (12)
C5	0.0309 (16)	0.0379 (14)	0.0327 (15)	0.0050 (12)	0.0039 (11)	−0.0019 (11)
C6	0.0427 (18)	0.0430 (15)	0.0372 (16)	0.0037 (13)	0.0016 (12)	−0.0028 (12)
C7	0.0348 (17)	0.0340 (14)	0.0313 (15)	0.0058 (13)	0.0030 (12)	−0.0011 (11)
C8	0.0380 (17)	0.0358 (14)	0.0408 (16)	0.0084 (14)	0.0005 (12)	0.0008 (11)
C9	0.0320 (16)	0.0419 (15)	0.0326 (15)	0.0000 (13)	0.0004 (12)	0.0023 (11)
C10	0.0298 (16)	0.0376 (14)	0.0282 (14)	−0.0023 (13)	0.0031 (11)	0.0054 (11)
C11	0.0310 (16)	0.0323 (13)	0.0259 (13)	−0.0017 (12)	0.0033 (11)	0.0011 (10)
C12	0.0360 (18)	0.0512 (17)	0.0509 (18)	0.0050 (15)	−0.0018 (13)	0.0007 (13)
C13	0.0307 (17)	0.0597 (18)	0.0552 (19)	−0.0032 (16)	−0.0046 (13)	−0.0001 (15)
C14	0.0427 (19)	0.0461 (16)	0.0466 (17)	−0.0047 (15)	−0.0061 (14)	−0.0030 (12)
C15	0.0354 (17)	0.0373 (15)	0.0407 (16)	−0.0003 (13)	−0.0004 (12)	0.0004 (12)
C16	0.0308 (16)	0.0344 (14)	0.0267 (14)	−0.0002 (13)	0.0021 (11)	−0.0014 (11)
C17	0.0344 (17)	0.0389 (15)	0.0348 (15)	0.0046 (13)	0.0023 (12)	−0.0019 (11)
C18	0.0343 (17)	0.0422 (16)	0.0284 (14)	0.0039 (14)	0.0026 (12)	0.0027 (11)
C19	0.0403 (17)	0.0348 (14)	0.0427 (16)	0.0098 (13)	−0.0045 (12)	−0.0019 (11)
C20	0.0291 (16)	0.0317 (14)	0.0479 (17)	−0.0012 (13)	0.0018 (12)	−0.0028 (12)
C21	0.0360 (18)	0.0400 (15)	0.063 (2)	0.0044 (14)	0.0078 (14)	0.0011 (13)
C22	0.052 (2)	0.0469 (17)	0.082 (3)	0.0066 (16)	0.0289 (18)	−0.0035 (16)
C23	0.070 (2)	0.0604 (19)	0.063 (2)	−0.0046 (19)	0.0314 (19)	−0.0062 (17)
C24	0.055 (2)	0.0675 (19)	0.0416 (18)	−0.0006 (17)	0.0048 (15)	0.0052 (14)
C25	0.0349 (17)	0.0518 (16)	0.0436 (17)	−0.0002 (14)	0.0065 (13)	−0.0037 (13)

N1—C11	1.390 (3)	C11—C16	1.418 (3)
N1—N2	1.394 (3)	C12—C13	1.379 (3)
N1—C7	1.403 (3)	C12—H12A	0.9500
N2—C17	1.335 (3)	C13—C14	1.398 (3)
O1—C18	1.215 (3)	C13—H13A	0.9500
O2—C18	1.377 (3)	C14—C15	1.389 (3)
O2—C19	1.458 (2)	C14—H14A	0.9500
C1—C2	1.387 (3)	C15—H15A	0.9500
C1—C6	1.387 (3)	C16—C17	1.414 (3)
C1—H1A	0.9500	C16—C18	1.472 (3)
C2—C3	1.387 (4)	C17—H17A	0.9500
C2—H2B	0.9500	C19—C20	1.511 (3)
C3—C4	1.394 (3)	C19—H19A	0.9900
C3—H3A	0.9500	C19—H19B	0.9900
C4—C5	1.400 (3)	C20—C21	1.397 (3)
C4—H4A	0.9500	C20—C25	1.401 (3)
C5—C6	1.403 (3)	C21—C22	1.395 (4)
C5—C7	1.496 (3)	C21—H21A	0.9500
C6—H6A	0.9500	C22—C23	1.379 (4)
C7—C8	1.360 (3)	C22—H22A	0.9500
C8—C9	1.438 (3)	C23—C24	1.394 (4)
C8—H8A	0.9500	C23—H23A	0.9500
C9—C12	1.417 (3)	C24—C25	1.389 (3)
C9—C10	1.427 (3)	C24—H24A	0.9500
C10—C15	1.410 (3)	C25—H25A	0.9500
C10—C11	1.460 (3)
C11—N1—N2	113.26 (18)	C12—C13—H13A	119.9
C11—N1—C7	125.3 (2)	C14—C13—H13A	119.9
N2—N1—C7	121.39 (18)	C15—C14—C13	120.4 (2)
C17—N2—N1	103.16 (19)	C15—C14—H14A	119.8
C18—O2—C19	116.05 (19)	C13—C14—H14A	119.8
C2—C1—C6	120.3 (2)	C14—C15—C10	120.7 (2)
C2—C1—H1A	119.8	C14—C15—H15A	119.7
C6—C1—H1A	119.8	C10—C15—H15A	119.7
C3—C2—C1	120.2 (2)	C17—C16—C11	105.01 (19)
C3—C2—H2B	119.9	C17—C16—C18	124.5 (2)
C1—C2—H2B	119.9	C11—C16—C18	130.4 (2)
C2—C3—C4	119.9 (2)	N2—C17—C16	113.8 (2)
C2—C3—H3A	120.0	N2—C17—H17A	123.1
C4—C3—H3A	120.0	C16—C17—H17A	123.1
C3—C4—C5	120.3 (2)	O1—C18—O2	122.1 (2)
C3—C4—H4A	119.8	O1—C18—C16	128.4 (2)
C5—C4—H4A	119.8	O2—C18—C16	109.6 (2)
C4—C5—C6	119.0 (2)	O2—C19—C20	111.82 (18)
C4—C5—C7	119.0 (2)	O2—C19—H19A	109.3
C6—C5—C7	121.9 (2)	C20—C19—H19A	109.3
C1—C6—C5	120.2 (2)	O2—C19—H19B	109.3
C1—C6—H6A	119.9	C20—C19—H19B	109.3
C5—C6—H6A	119.9	H19A—C19—H19B	107.9
C8—C7—N1	117.0 (2)	C21—C20—C25	117.8 (2)
C8—C7—C5	123.4 (2)	C21—C20—C19	119.9 (2)
N1—C7—C5	119.6 (2)	C25—C20—C19	122.3 (2)
C7—C8—C9	122.3 (2)	C22—C21—C20	121.0 (3)
C7—C8—H8A	118.9	C22—C21—H21A	119.5
C9—C8—H8A	118.9	C20—C21—H21A	119.5
C12—C9—C10	118.8 (2)	C23—C22—C21	120.3 (3)
C12—C9—C8	121.1 (2)	C23—C22—H22A	119.9
C10—C9—C8	120.1 (2)	C21—C22—H22A	119.9
C15—C10—C9	119.0 (2)	C22—C23—C24	119.9 (3)
C15—C10—C11	123.4 (2)	C22—C23—H23A	120.1
C9—C10—C11	117.6 (2)	C24—C23—H23A	120.1
N1—C11—C16	104.8 (2)	C25—C24—C23	119.7 (3)
N1—C11—C10	117.6 (2)	C25—C24—H24A	120.1
C16—C11—C10	137.6 (2)	C23—C24—H24A	120.1
C13—C12—C9	121.0 (2)	C24—C25—C20	121.4 (3)
C13—C12—H12A	119.5	C24—C25—H25A	119.3
C9—C12—H12A	119.5	C20—C25—H25A	119.3
C12—C13—C14	120.1 (2)
C11—N1—N2—C17	0.4 (2)	C9—C10—C11—C16	178.3 (2)
C7—N1—N2—C17	177.82 (19)	C10—C9—C12—C13	1.7 (4)
C6—C1—C2—C3	0.5 (4)	C8—C9—C12—C13	−179.1 (2)
C1—C2—C3—C4	0.2 (4)	C9—C12—C13—C14	0.7 (4)
C2—C3—C4—C5	−1.0 (4)	C12—C13—C14—C15	−2.5 (4)
C3—C4—C5—C6	1.0 (4)	C13—C14—C15—C10	1.9 (4)
C3—C4—C5—C7	−174.8 (2)	C9—C10—C15—C14	0.5 (3)
C2—C1—C6—C5	−0.5 (4)	C11—C10—C15—C14	−179.2 (2)
C4—C5—C6—C1	−0.3 (4)	N1—C11—C16—C17	0.8 (2)
C7—C5—C6—C1	175.4 (2)	C10—C11—C16—C17	−176.7 (2)
C11—N1—C7—C8	−0.3 (3)	N1—C11—C16—C18	−177.4 (2)
N2—N1—C7—C8	−177.46 (19)	C10—C11—C16—C18	5.1 (4)
C11—N1—C7—C5	−179.4 (2)	N1—N2—C17—C16	0.2 (2)
N2—N1—C7—C5	3.4 (3)	C11—C16—C17—N2	−0.7 (3)
C4—C5—C7—C8	54.6 (3)	C18—C16—C17—N2	177.6 (2)
C6—C5—C7—C8	−121.1 (3)	C19—O2—C18—O1	0.0 (3)
C4—C5—C7—N1	−126.4 (2)	C19—O2—C18—C16	−179.81 (17)
C6—C5—C7—N1	58.0 (3)	C17—C16—C18—O1	−171.4 (2)
N1—C7—C8—C9	−0.4 (3)	C11—C16—C18—O1	6.5 (4)
C5—C7—C8—C9	178.6 (2)	C17—C16—C18—O2	8.4 (3)
C7—C8—C9—C12	−177.7 (2)	C11—C16—C18—O2	−173.7 (2)
C7—C8—C9—C10	1.5 (4)	C18—O2—C19—C20	−96.2 (2)
C12—C9—C10—C15	−2.2 (3)	O2—C19—C20—C21	−137.2 (2)
C8—C9—C10—C15	178.5 (2)	O2—C19—C20—C25	43.3 (3)
C12—C9—C10—C11	177.5 (2)	C25—C20—C21—C22	1.5 (3)
C8—C9—C10—C11	−1.7 (3)	C19—C20—C21—C22	−178.0 (2)
N2—N1—C11—C16	−0.8 (2)	C20—C21—C22—C23	−1.2 (4)
C7—N1—C11—C16	−178.12 (19)	C21—C22—C23—C24	0.5 (4)
N2—N1—C11—C10	177.36 (18)	C22—C23—C24—C25	−0.1 (4)
C7—N1—C11—C10	0.0 (3)	C23—C24—C25—C20	0.5 (4)
C15—C10—C11—N1	−179.3 (2)	C21—C20—C25—C24	−1.2 (3)
C9—C10—C11—N1	1.0 (3)	C19—C20—C25—C24	178.4 (2)
C15—C10—C11—C16	−1.9 (4)

Cg1 and Cg2 are the centroids of the N1/N2C11/C16/C17 and C20–C25 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O1	0.95	2.17	3.012 (3)	148
C1—H1A···Cg1i	0.95	2.76	3.484 (3)	134
C14—H14A···Cg2ii	0.95	2.68	3.594 (3)	161

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N1/N2C11/C16/C17 and C20–C25 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O1	0.95	2.17	3.012 (3)	148
C1—H1A⋯Cg1i	0.95	2.76	3.484 (3)	134
C14—H14A⋯Cg2ii	0.95	2.68	3.594 (3)	161

Symmetry codes: (i) ; (ii) .