Crystal structure of 13-phenyl-2,3,4,13-tetra-hydro-1H-indazolo[1,2-b]phthalazine-1,6,11-trione.

The title compound, C21H16N2O3, consists of an indazolone moiety, bearing a phenyl group, fused to a phthalazine ring system (r.m.s. deviation = 0.018 Å). The phenyl ring is almost normal to the mean plane of the five-membered ring of the indazolone moiety, making a dihedral angle of 89.64 (7)°. The six-membered ring of the indazolone moiety has an envelope conformation, with the central methyl-ene C atom as the flap. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds, forming slabs parallel to the bc plane. The slabs are linked via C-H⋯π and π-π inter-actions [the shortest inter-centroid distance involving rings of pyrazolo-phthalazine moieties is 3.6430 (8) Å], forming a three-dimensional structure.

Related literature

For application of phthalazine derivatives see: Mosaddegh & Hassankhani (2011 ▸); Hasaninejed et al. (2012 ▸); Keshipour et al. (2012 ▸). For the synthesis of this class of compounds, see: Carling et al. (2004 ▸); Cashman & Ghirmai (2009 ▸); Hall et al. (1992 ▸, 2001 ▸); Bouraiou et al. (2015 ▸); Nomoto et al. (1990 ▸). For the synthesis of the title compound, see: Bouraiou et al. (2015 ▸); Khurana & Magoo (2009 ▸); Nagarapu et al. (2009 ▸).

Experimental

Crystal data

C21H16N2O3

M = 344.36

Monoclinic,

a = 8.9028 (2) Å

b = 11.4507 (3) Å

c = 17.0274 (4) Å

β = 104.618 (1)°

V = 1679.64 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.13 × 0.09 × 0.05 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2011 ▸) T min = 0.957, T max = 0.986

4873 measured reflections

4873 independent reflections

3617 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.182

S = 1.12

4873 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.6 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2011 ▸); cell refinement: SAINT (Bruker, 2011 ▸); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015023452/su5255sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015023452/su5255Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015023452/su5255Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015023452/su5255fig1.tif

The mol­ecule structure of the title compound, with atom labelling. Displacement are drawn at the 50% probability level.

Click here for additional data file.

a . DOI: 10.1107/S2056989015023452/su5255fig2.tif

A view along the a axis of the crystal packing of the title compound, showing the C—H⋯O hydrogen bonds as dashed lines (see Table 1).

CCDC reference: 1440831

Additional supporting information: crystallographic information; 3D view; checkCIF report

C21H16N2O3	F(000) = 720
Mr = 344.36	Dx = 1.362 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4002 reflections
a = 8.9028 (2) Å	θ = 3.0–30.5°
b = 11.4507 (3) Å	µ = 0.09 mm−1
c = 17.0274 (4) Å	T = 295 K
β = 104.618 (1)°	Prism, yellow
V = 1679.64 (7) Å3	0.13 × 0.09 × 0.05 mm
Z = 4

Bruker APEXII diffractometer	4873 independent reflections
Radiation source: Enraf Nonius FR590	3617 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0
CCD rotation images, thick slices scans	θmax = 30.6°, θmin = 3.4°
Absorption correction: multi-scan (SADABS; Bruker, 2011)	h = −12→12
Tmin = 0.957, Tmax = 0.986	k = 0→16
4873 measured reflections	l = 0→23

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) = 0.182	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.1115P)2 + 0.0058P] where P = (Fo2 + 2Fc2)/3
4873 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.6 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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
C1	0.75069 (15)	0.02395 (11)	0.00764 (7)	0.0373 (3)
C2	0.68676 (14)	−0.05024 (11)	0.06179 (7)	0.0350 (3)
C3	0.69309 (16)	−0.17117 (12)	0.05347 (9)	0.0452 (3)
H3	0.7353	−0.2031	0.0136	0.054*
C4	0.63708 (18)	−0.24340 (13)	0.10405 (10)	0.0519 (4)
H4	0.6422	−0.324	0.0986	0.062*
C5	0.57284 (17)	−0.19596 (15)	0.16328 (10)	0.0525 (4)
H5	0.5359	−0.245	0.1977	0.063*
C6	0.56360 (16)	−0.07659 (14)	0.17128 (9)	0.0455 (3)
H6	0.5189	−0.0454	0.2105	0.055*
C7	0.62114 (13)	−0.00234 (12)	0.12069 (7)	0.0359 (3)
C8	0.60888 (14)	0.12553 (12)	0.12975 (7)	0.0369 (3)
C9	0.66558 (13)	0.31891 (11)	0.07410 (7)	0.0332 (3)
H9	0.5574	0.3454	0.0611	0.04*
C10	0.73305 (14)	0.33728 (11)	0.00262 (7)	0.0350 (3)
C11	0.74291 (16)	0.44774 (12)	−0.03792 (8)	0.0425 (3)
C12	0.8090 (2)	0.43883 (17)	−0.11124 (11)	0.0664 (5)
H12A	0.7242	0.4281	−0.1592	0.08*
H12B	0.8599	0.5119	−0.1175	0.08*
C13	0.9230 (3)	0.34114 (17)	−0.10670 (12)	0.0689 (5)
H13A	1.0152	0.358	−0.0639	0.083*
H13B	0.9534	0.3375	−0.1575	0.083*
C14	0.85967 (17)	0.22277 (14)	−0.09042 (8)	0.0464 (3)
H14A	0.7873	0.1942	−0.1392	0.056*
H14B	0.9439	0.167	−0.0747	0.056*
C15	0.77933 (14)	0.23569 (11)	−0.02380 (7)	0.0347 (3)
C16	0.75871 (13)	0.37878 (11)	0.15078 (7)	0.0329 (3)
C17	0.91360 (15)	0.35115 (14)	0.18289 (8)	0.0455 (3)
H17	0.9599	0.2926	0.1593	0.055*
C18	1.00001 (17)	0.41101 (16)	0.25044 (8)	0.0532 (4)
H18	1.1036	0.3916	0.2723	0.064*
C19	0.93283 (19)	0.49868 (14)	0.28486 (8)	0.0504 (4)
H19	0.9917	0.5398	0.3291	0.06*
C20	0.7781 (2)	0.52582 (13)	0.25386 (8)	0.0510 (4)
H20	0.7319	0.5841	0.2778	0.061*
C21	0.69169 (16)	0.46548 (12)	0.18660 (8)	0.0414 (3)
H21	0.5875	0.4839	0.1656	0.05*
N1	0.74174 (12)	0.14291 (9)	0.02082 (6)	0.0351 (2)
N2	0.67235 (12)	0.19043 (10)	0.07981 (6)	0.0355 (2)
O1	0.80699 (15)	−0.01280 (10)	−0.04590 (6)	0.0574 (3)
O2	0.54814 (13)	0.17285 (10)	0.17821 (6)	0.0539 (3)
O3	0.69339 (14)	0.53847 (10)	−0.01668 (7)	0.0591 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0465 (6)	0.0302 (6)	0.0353 (6)	0.0009 (5)	0.0105 (5)	0.0003 (5)
C2	0.0378 (6)	0.0291 (6)	0.0350 (6)	−0.0002 (5)	0.0031 (4)	0.0034 (4)
C3	0.0509 (7)	0.0333 (7)	0.0476 (7)	0.0004 (6)	0.0055 (6)	0.0010 (5)
C4	0.0562 (8)	0.0319 (7)	0.0630 (9)	−0.0035 (6)	0.0064 (7)	0.0072 (6)
C5	0.0506 (7)	0.0452 (8)	0.0599 (9)	−0.0093 (7)	0.0109 (6)	0.0166 (7)
C6	0.0442 (7)	0.0452 (8)	0.0483 (7)	−0.0045 (6)	0.0139 (5)	0.0077 (6)
C7	0.0345 (6)	0.0353 (7)	0.0359 (6)	−0.0030 (5)	0.0049 (4)	0.0035 (5)
C8	0.0389 (6)	0.0371 (7)	0.0362 (6)	−0.0031 (5)	0.0120 (4)	0.0007 (5)
C9	0.0361 (5)	0.0289 (6)	0.0347 (6)	0.0007 (5)	0.0093 (4)	−0.0005 (4)
C10	0.0397 (6)	0.0333 (7)	0.0314 (5)	−0.0019 (5)	0.0079 (4)	0.0008 (4)
C11	0.0483 (7)	0.0347 (7)	0.0437 (7)	−0.0015 (6)	0.0103 (5)	0.0054 (5)
C12	0.0946 (13)	0.0509 (10)	0.0660 (10)	0.0039 (9)	0.0433 (9)	0.0181 (8)
C13	0.0916 (13)	0.0537 (11)	0.0784 (11)	−0.0096 (9)	0.0530 (10)	0.0009 (9)
C14	0.0575 (8)	0.0435 (8)	0.0449 (7)	−0.0030 (7)	0.0254 (6)	−0.0026 (6)
C15	0.0395 (6)	0.0325 (6)	0.0325 (6)	−0.0035 (5)	0.0097 (4)	−0.0003 (5)
C16	0.0388 (6)	0.0304 (6)	0.0307 (5)	−0.0023 (5)	0.0110 (4)	0.0020 (4)
C17	0.0405 (6)	0.0532 (9)	0.0426 (6)	0.0032 (6)	0.0101 (5)	−0.0055 (6)
C18	0.0423 (7)	0.0717 (12)	0.0419 (7)	−0.0076 (7)	0.0037 (5)	0.0002 (7)
C19	0.0636 (9)	0.0497 (8)	0.0348 (6)	−0.0164 (7)	0.0068 (6)	−0.0031 (6)
C20	0.0734 (10)	0.0380 (7)	0.0417 (7)	0.0005 (7)	0.0145 (6)	−0.0052 (6)
C21	0.0491 (7)	0.0354 (7)	0.0399 (6)	0.0057 (6)	0.0115 (5)	0.0002 (5)
N1	0.0445 (5)	0.0300 (5)	0.0341 (5)	−0.0001 (4)	0.0159 (4)	−0.0015 (4)
N2	0.0449 (5)	0.0295 (5)	0.0362 (5)	−0.0021 (4)	0.0178 (4)	−0.0020 (4)
O1	0.0895 (8)	0.0395 (6)	0.0544 (6)	0.0026 (6)	0.0389 (6)	−0.0047 (5)
O2	0.0670 (7)	0.0471 (7)	0.0603 (6)	−0.0031 (5)	0.0394 (5)	−0.0030 (5)
O3	0.0773 (8)	0.0356 (6)	0.0685 (7)	0.0087 (5)	0.0262 (6)	0.0081 (5)

C1—O1	1.2206 (16)	C11—C12	1.512 (2)
C1—N1	1.3861 (16)	C12—C13	1.499 (3)
C1—C2	1.4700 (18)	C12—H12A	0.97
C2—C7	1.3942 (19)	C12—H12B	0.97
C2—C3	1.3945 (19)	C13—C14	1.520 (2)
C3—C4	1.375 (2)	C13—H13A	0.97
C3—H3	0.93	C13—H13B	0.97
C4—C5	1.389 (3)	C14—C15	1.4932 (19)
C4—H4	0.93	C14—H14A	0.97
C5—C6	1.378 (2)	C14—H14B	0.97
C5—H5	0.93	C15—N1	1.3951 (16)
C6—C7	1.3964 (18)	C16—C21	1.3775 (18)
C6—H6	0.93	C16—C17	1.3857 (18)
C7—C8	1.4793 (19)	C17—C18	1.3921 (19)
C8—O2	1.2215 (16)	C17—H17	0.93
C8—N2	1.3554 (16)	C18—C19	1.373 (2)
C9—N2	1.4746 (17)	C18—H18	0.93
C9—C10	1.5019 (17)	C19—C20	1.381 (2)
C9—C16	1.5217 (16)	C19—H19	0.93
C9—H9	0.98	C20—C21	1.3915 (19)
C10—C15	1.3487 (18)	C20—H20	0.93
C10—C11	1.4541 (18)	C21—H21	0.93
C11—O3	1.2187 (18)	N1—N2	1.4142 (14)
O1—C1—N1	120.73 (12)	H12A—C12—H12B	107.6
O1—C1—C2	124.48 (13)	C12—C13—C14	113.43 (16)
N1—C1—C2	114.78 (11)	C12—C13—H13A	108.9
C7—C2—C3	119.92 (13)	C14—C13—H13A	108.9
C7—C2—C1	121.51 (12)	C12—C13—H13B	108.9
C3—C2—C1	118.57 (13)	C14—C13—H13B	108.9
C4—C3—C2	120.21 (15)	H13A—C13—H13B	107.7
C4—C3—H3	119.9	C15—C14—C13	108.72 (12)
C2—C3—H3	119.9	C15—C14—H14A	109.9
C3—C4—C5	120.01 (15)	C13—C14—H14A	109.9
C3—C4—H4	120	C15—C14—H14B	109.9
C5—C4—H4	120	C13—C14—H14B	109.9
C6—C5—C4	120.36 (14)	H14A—C14—H14B	108.3
C6—C5—H5	119.8	C10—C15—N1	109.86 (11)
C4—C5—H5	119.8	C10—C15—C14	125.73 (12)
C5—C6—C7	120.17 (15)	N1—C15—C14	124.41 (12)
C5—C6—H6	119.9	C21—C16—C17	119.28 (12)
C7—C6—H6	119.9	C21—C16—C9	120.10 (11)
C2—C7—C6	119.32 (13)	C17—C16—C9	120.54 (11)
C2—C7—C8	121.32 (11)	C16—C17—C18	120.07 (14)
C6—C7—C8	119.35 (12)	C16—C17—H17	120
O2—C8—N2	120.42 (13)	C18—C17—H17	120
O2—C8—C7	124.50 (12)	C19—C18—C17	120.21 (13)
N2—C8—C7	115.08 (11)	C19—C18—H18	119.9
N2—C9—C10	100.09 (10)	C17—C18—H18	119.9
N2—C9—C16	112.86 (9)	C18—C19—C20	120.09 (13)
C10—C9—C16	112.92 (10)	C18—C19—H19	120
N2—C9—H9	110.2	C20—C19—H19	120
C10—C9—H9	110.2	C19—C20—C21	119.60 (14)
C16—C9—H9	110.2	C19—C20—H20	120.2
C15—C10—C11	122.13 (12)	C21—C20—H20	120.2
C15—C10—C9	111.58 (11)	C16—C21—C20	120.74 (13)
C11—C10—C9	126.22 (12)	C16—C21—H21	119.6
O3—C11—C10	122.07 (13)	C20—C21—H21	119.6
O3—C11—C12	123.22 (13)	C1—N1—C15	128.95 (11)
C10—C11—C12	114.58 (13)	C1—N1—N2	123.12 (11)
C13—C12—C11	114.02 (14)	C15—N1—N2	107.56 (10)
C13—C12—H12A	108.7	C8—N2—N1	124.10 (11)
C11—C12—H12A	108.7	C8—N2—C9	124.87 (11)
C13—C12—H12B	108.7	N1—N2—C9	110.79 (9)
C11—C12—H12B	108.7

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2i	0.93	2.59	3.488 (2)	163
C9—H9···O3ii	0.98	2.54	3.501 (2)	165
C18—H18···Cg3iii	0.93	2.68	3.552 (2)	156

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2i	0.93	2.59	3.488 (2)	163
C9—H9⋯O3ii	0.98	2.54	3.501 (2)	165
C18—H18⋯Cg3iii	0.93	2.68	3.552 (2)	156

Symmetry codes: (i) ; (ii) ; (iii) .