7-Methyl-1-phenyl-1,10-di-hydro-pyrazolo-[3,4-a]carbazole.

In the title mol-ecule, C20H15N3, the atoms in the carbazole unit deviate from planarity [maximum deviation from mean plane = 0.1082 (15) Å]. The pyrrole ring makes dihedral angles of 3.17 (8)/4.10 (9), 7.20 (9) and 44.62 (9)° with the fused benzene, pyrazole and phenyl rings, respectively. In the crystal, mol-ecules are linked via N-H⋯N hydrogen bonds, forming an infinite chain along [010]. Mol-ecules are further linked by nine π-π [centroid-centroid distances vary from 3.6864 (11) to 3.9802 (11) Å] and one C-H⋯π inter-action, forming a three-dimensional network.

Related literature

For related structures and the biological and pharmacological activity of carbazole alkaloids, see: Archana et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C20H15N3

M = 297.35

Monoclinic,

a = 12.0727 (6) Å

b = 7.5934 (3) Å

c = 16.8355 (8) Å

β = 104.087 (5)°

V = 1496.95 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 123 K

0.43 × 0.35 × 0.30 mm

Data collection

Agilent Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.967, T max = 0.977

6773 measured reflections

3212 independent reflections

2354 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.115

S = 1.03

3212 reflections

213 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813010994/bg2506sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813010994/bg2506Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813010994/bg2506Isup3.cdx

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813010994/bg2506Isup4.cml

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

C20H15N3	F(000) = 624
Mr = 297.35	Dx = 1.319 Mg m−3
Monoclinic, P21/c	Melting point: 509 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.0727 (6) Å	Cell parameters from 2152 reflections
b = 7.5934 (3) Å	θ = 3.2–28.7°
c = 16.8355 (8) Å	µ = 0.08 mm−1
β = 104.087 (5)°	T = 123 K
V = 1496.95 (12) Å3	Block, colourless
Z = 4	0.43 × 0.35 × 0.30 mm

Agilent Xcalibur Ruby Gemini diffractometer	3212 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2354 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 10.5081 pixels mm-1	θmax = 28.8°, θmin = 3.2°
ω scans	h = −11→15
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −9→9
Tmin = 0.967, Tmax = 0.977	l = −22→17
6773 measured reflections

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0374P)2 + 0.6346P] where P = (Fo2 + 2Fc2)/3
3212 reflections	(Δ/σ)max = 0.001
213 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 > 2σ(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	0.02985 (12)	1.03390 (19)	0.21043 (9)	0.0239 (4)
N2	−0.00637 (13)	1.1004 (2)	0.13198 (9)	0.0282 (5)
N10	0.20532 (12)	0.85847 (19)	0.37045 (9)	0.0218 (5)
C3	0.08613 (15)	1.1075 (2)	0.10345 (11)	0.0279 (6)
C3A	0.18491 (15)	1.0494 (2)	0.16110 (10)	0.0226 (5)
C4	0.30269 (15)	1.0405 (3)	0.16171 (11)	0.0276 (6)
C5	0.37898 (16)	0.9927 (3)	0.23251 (11)	0.0296 (6)
C5A	0.33861 (14)	0.9308 (2)	0.30042 (11)	0.0229 (5)
C5B	0.39645 (14)	0.8572 (2)	0.37826 (10)	0.0216 (5)
C6	0.51173 (15)	0.8333 (2)	0.41785 (11)	0.0244 (5)
C7	0.54120 (15)	0.7615 (2)	0.49534 (11)	0.0255 (5)
C8	0.45442 (16)	0.7109 (2)	0.53306 (11)	0.0270 (6)
C9	0.33971 (15)	0.7336 (2)	0.49600 (11)	0.0255 (6)
C9A	0.31196 (14)	0.8101 (2)	0.41843 (10)	0.0217 (5)
C10A	0.22194 (14)	0.9297 (2)	0.29845 (10)	0.0210 (5)
C10B	0.14522 (14)	1.0011 (2)	0.22935 (10)	0.0199 (5)
C11	−0.04799 (14)	1.0332 (2)	0.26172 (11)	0.0229 (5)
C12	−0.01450 (16)	1.0956 (2)	0.34141 (11)	0.0263 (5)
C13	−0.09314 (17)	1.0990 (3)	0.38894 (12)	0.0322 (6)
C14	−0.20453 (17)	1.0443 (3)	0.35701 (13)	0.0360 (7)
C15	−0.23685 (17)	0.9846 (3)	0.27740 (13)	0.0350 (7)
C16	−0.15914 (15)	0.9769 (2)	0.22938 (12)	0.0290 (6)
C17	0.66497 (15)	0.7377 (3)	0.54049 (12)	0.0315 (6)
H3	0.08626	1.14732	0.04998	0.0334*
H4	0.32788	1.06729	0.11384	0.0331*
H5	0.45869	1.00054	0.23653	0.0355*
H6	0.56955	0.86651	0.39130	0.0292*
H8	0.47522	0.65913	0.58598	0.0324*
H9	0.28215	0.69847	0.52242	0.0306*
H10	0.1399 (17)	0.809 (3)	0.3743 (12)	0.034 (6)*
H12	0.06146	1.13546	0.36304	0.0316*
H13	−0.07056	1.13924	0.44395	0.0387*
H14	−0.25836	1.04795	0.38980	0.0431*
H15	−0.31347	0.94826	0.25532	0.0420*
H16	−0.18151	0.93355	0.17487	0.0348*
H17A	0.68418	0.61209	0.54327	0.0473*
H17B	0.67687	0.78502	0.59609	0.0473*
H17C	0.71401	0.80058	0.51136	0.0473*

	U11	U22	U33	U12	U13	U23
N1	0.0196 (7)	0.0276 (8)	0.0234 (8)	0.0030 (7)	0.0032 (6)	0.0019 (6)
N2	0.0261 (8)	0.0322 (9)	0.0243 (8)	0.0044 (7)	0.0025 (7)	0.0044 (7)
N10	0.0192 (8)	0.0238 (8)	0.0222 (8)	−0.0024 (7)	0.0046 (7)	0.0009 (6)
C3	0.0307 (10)	0.0284 (10)	0.0246 (10)	0.0024 (9)	0.0068 (8)	0.0013 (8)
C3A	0.0254 (9)	0.0205 (9)	0.0212 (9)	0.0002 (8)	0.0042 (8)	−0.0021 (7)
C4	0.0277 (10)	0.0350 (11)	0.0216 (9)	−0.0024 (9)	0.0092 (8)	0.0000 (8)
C5	0.0225 (9)	0.0362 (11)	0.0324 (11)	0.0012 (9)	0.0113 (9)	0.0046 (9)
C5A	0.0204 (9)	0.0216 (9)	0.0260 (10)	0.0005 (8)	0.0046 (8)	−0.0014 (7)
C5B	0.0217 (9)	0.0186 (8)	0.0241 (9)	0.0005 (8)	0.0050 (8)	−0.0030 (7)
C6	0.0210 (9)	0.0213 (9)	0.0302 (10)	0.0004 (8)	0.0051 (8)	−0.0028 (8)
C7	0.0269 (9)	0.0175 (9)	0.0282 (10)	0.0025 (8)	−0.0007 (8)	−0.0056 (7)
C8	0.0334 (10)	0.0212 (9)	0.0230 (10)	0.0021 (8)	0.0005 (8)	0.0000 (8)
C9	0.0288 (10)	0.0223 (9)	0.0255 (10)	−0.0016 (8)	0.0069 (8)	−0.0028 (8)
C9A	0.0226 (9)	0.0187 (9)	0.0224 (9)	−0.0008 (8)	0.0029 (8)	−0.0033 (7)
C10A	0.0220 (9)	0.0199 (9)	0.0211 (9)	−0.0006 (7)	0.0052 (8)	−0.0017 (7)
C10B	0.0170 (9)	0.0196 (9)	0.0223 (9)	0.0000 (7)	0.0031 (7)	−0.0032 (7)
C11	0.0215 (9)	0.0197 (9)	0.0279 (10)	0.0037 (8)	0.0069 (8)	0.0032 (8)
C12	0.0244 (9)	0.0232 (9)	0.0311 (10)	0.0003 (8)	0.0062 (8)	−0.0014 (8)
C13	0.0381 (11)	0.0279 (10)	0.0342 (11)	0.0022 (9)	0.0155 (9)	−0.0014 (9)
C14	0.0351 (11)	0.0308 (11)	0.0488 (13)	0.0008 (9)	0.0234 (10)	0.0013 (10)
C15	0.0230 (10)	0.0297 (10)	0.0532 (14)	−0.0016 (9)	0.0109 (10)	0.0030 (10)
C16	0.0233 (10)	0.0268 (10)	0.0348 (11)	−0.0008 (8)	0.0030 (8)	−0.0007 (8)
C17	0.0282 (10)	0.0279 (10)	0.0324 (11)	0.0064 (9)	−0.0044 (9)	−0.0059 (8)

N1—N2	1.382 (2)	C10A—C10B	1.407 (2)
N1—C10B	1.374 (2)	C11—C16	1.387 (3)
N1—C11	1.423 (2)	C11—C12	1.387 (2)
N2—C3	1.320 (2)	C12—C13	1.383 (3)
N10—C9A	1.392 (2)	C13—C14	1.385 (3)
N10—C10A	1.386 (2)	C14—C15	1.378 (3)
N10—H10	0.89 (2)	C15—C16	1.381 (3)
C3—C3A	1.413 (2)	C3—H3	0.9500
C3A—C4	1.421 (3)	C4—H4	0.9500
C3A—C10B	1.397 (2)	C5—H5	0.9500
C4—C5	1.366 (3)	C6—H6	0.9500
C5—C5A	1.427 (3)	C8—H8	0.9500
C5A—C5B	1.439 (2)	C9—H9	0.9500
C5A—C10A	1.401 (2)	C12—H12	0.9500
C5B—C9A	1.401 (2)	C13—H13	0.9500
C5B—C6	1.401 (3)	C14—H14	0.9500
C6—C7	1.378 (2)	C15—H15	0.9500
C7—C8	1.404 (3)	C16—H16	0.9500
C7—C17	1.513 (3)	C17—H17A	0.9800
C8—C9	1.384 (3)	C17—H17B	0.9800
C9—C9A	1.394 (2)	C17—H17C	0.9800
N2—N1—C10B	110.79 (14)	C12—C11—C16	120.75 (17)
N2—N1—C11	118.65 (14)	N1—C11—C16	118.80 (16)
C10B—N1—C11	129.85 (15)	C11—C12—C13	119.11 (18)
N1—N2—C3	105.30 (15)	C12—C13—C14	120.56 (18)
C9A—N10—C10A	107.47 (14)	C13—C14—C15	119.63 (19)
C9A—N10—H10	123.9 (14)	C14—C15—C16	120.76 (19)
C10A—N10—H10	123.2 (13)	C11—C16—C15	119.17 (18)
N2—C3—C3A	112.63 (16)	N2—C3—H3	124.00
C4—C3A—C10B	121.63 (16)	C3A—C3—H3	124.00
C3—C3A—C4	134.09 (16)	C3A—C4—H4	121.00
C3—C3A—C10B	104.23 (16)	C5—C4—H4	121.00
C3A—C4—C5	118.68 (17)	C4—C5—H5	120.00
C4—C5—C5A	119.82 (18)	C5A—C5—H5	120.00
C5B—C5A—C10A	106.35 (15)	C5B—C6—H6	120.00
C5—C5A—C10A	121.36 (16)	C7—C6—H6	120.00
C5—C5A—C5B	132.27 (17)	C7—C8—H8	119.00
C5A—C5B—C6	133.56 (16)	C9—C8—H8	119.00
C5A—C5B—C9A	106.85 (15)	C8—C9—H9	121.00
C6—C5B—C9A	119.55 (15)	C9A—C9—H9	121.00
C5B—C6—C7	119.95 (17)	C11—C12—H12	120.00
C8—C7—C17	119.62 (16)	C13—C12—H12	120.00
C6—C7—C8	119.15 (17)	C12—C13—H13	120.00
C6—C7—C17	121.23 (17)	C14—C13—H13	120.00
C7—C8—C9	122.46 (16)	C13—C14—H14	120.00
C8—C9—C9A	117.40 (16)	C15—C14—H14	120.00
N10—C9A—C9	129.13 (16)	C14—C15—H15	120.00
N10—C9A—C5B	109.38 (14)	C16—C15—H15	120.00
C5B—C9A—C9	121.45 (16)	C11—C16—H16	120.00
C5A—C10A—C10B	118.22 (15)	C15—C16—H16	120.00
N10—C10A—C10B	131.84 (16)	C7—C17—H17A	109.00
N10—C10A—C5A	109.90 (15)	C7—C17—H17B	109.00
N1—C10B—C3A	107.04 (14)	C7—C17—H17C	109.00
N1—C10B—C10A	133.44 (16)	H17A—C17—H17B	109.00
C3A—C10B—C10A	119.50 (16)	H17A—C17—H17C	109.00
N1—C11—C12	120.38 (16)	H17B—C17—H17C	109.00
C10B—N1—N2—C3	0.15 (18)	C5—C5A—C10A—N10	178.07 (16)
C11—N1—N2—C3	171.43 (14)	C5—C5A—C10A—C10B	−3.7 (2)
N2—N1—C10B—C3A	0.50 (18)	C5B—C5A—C10A—N10	−0.41 (18)
N2—N1—C10B—C10A	−177.71 (17)	C5B—C5A—C10A—C10B	177.85 (14)
C11—N1—C10B—C3A	−169.53 (15)	C5A—C5B—C6—C7	178.06 (17)
C11—N1—C10B—C10A	12.3 (3)	C9A—C5B—C6—C7	0.9 (2)
N2—N1—C11—C12	−132.06 (16)	C5A—C5B—C9A—N10	−2.61 (18)
N2—N1—C11—C16	44.9 (2)	C5A—C5B—C9A—C9	179.74 (14)
C10B—N1—C11—C12	37.3 (2)	C6—C5B—C9A—N10	175.22 (14)
C10B—N1—C11—C16	−145.69 (17)	C6—C5B—C9A—C9	−2.4 (2)
N1—N2—C3—C3A	−0.76 (18)	C5B—C6—C7—C8	0.9 (2)
C10A—N10—C9A—C5B	2.37 (18)	C5B—C6—C7—C17	−178.63 (16)
C10A—N10—C9A—C9	179.78 (16)	C6—C7—C8—C9	−1.3 (2)
C9A—N10—C10A—C5A	−1.18 (18)	C17—C7—C8—C9	178.20 (16)
C9A—N10—C10A—C10B	−179.12 (16)	C7—C8—C9—C9A	−0.1 (2)
N2—C3—C3A—C4	−176.18 (19)	C8—C9—C9A—N10	−175.15 (16)
N2—C3—C3A—C10B	1.05 (18)	C8—C9—C9A—C5B	2.0 (2)
C3—C3A—C4—C5	173.19 (19)	N10—C10A—C10B—N1	4.0 (3)
C10B—C3A—C4—C5	−3.7 (3)	N10—C10A—C10B—C3A	−174.02 (16)
C3—C3A—C10B—N1	−0.89 (17)	C5A—C10A—C10B—N1	−173.79 (17)
C3—C3A—C10B—C10A	177.62 (14)	C5A—C10A—C10B—C3A	8.2 (2)
C4—C3A—C10B—N1	176.78 (16)	N1—C11—C12—C13	177.78 (16)
C4—C3A—C10B—C10A	−4.7 (2)	C16—C11—C12—C13	0.8 (2)
C3A—C4—C5—C5A	8.2 (3)	N1—C11—C16—C15	−176.60 (16)
C4—C5—C5A—C5B	173.34 (19)	C12—C11—C16—C15	0.4 (2)
C4—C5—C5A—C10A	−4.7 (3)	C11—C12—C13—C14	−1.3 (3)
C5—C5A—C5B—C6	6.2 (3)	C12—C13—C14—C15	0.6 (3)
C5—C5A—C5B—C9A	−176.42 (19)	C13—C14—C15—C16	0.7 (3)
C10A—C5A—C5B—C6	−175.56 (17)	C14—C15—C16—C11	−1.2 (3)
C10A—C5A—C5B—C9A	1.83 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N10—H10···N2i	0.89 (2)	2.24 (2)	3.092 (2)	159 (2)
C17—H17B···Cg2ii	0.98	2.70	3.401 (2)	129

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the N10/C10A/C5A/C5B/C9A pyrrole ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N10—H10⋯N2i	0.89 (2)	2.24 (2)	3.092 (2)	159 (2)
C17—H17B⋯Cg2ii	0.98	2.70	3.401 (2)	129

Symmetry codes: (i) ; (ii) .