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Acta Cryst. (2007). E63, o3471
https://doi.org/10.1107/S160053680703351X
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1,10-Dihydro-3,9-dimethyl­pyrazolo[3,4-a]carbazole

A. E. Martin, A. T. Gunaseelan, A. Thiruvalluvar, K. J. R. Prasad and R. J. Butcher
The heterofused carbazole unit of the title compound, C15H13N3, is planar. The planar pyrazole ring forms dihedral angles of 1.08 (7), 0.64 (6) and 2.60 (7)° with the pyrrole, fused benzene and methyl-substituted benzene rings, respectively. The methyl group on the five-membered ring is disordered equally over two positions. In the crystal structure, the mol­ecules are stabilized by inter­molecular N—H...N hydrogen bonds.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680703351X/bq2027sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680703351X/bq2027Isup2.hkl
Contains datablock I

CCDC reference: 657744

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 203 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.043
  • wR factor = 0.096
  • Data-to-parameter ratio = 22.9

checkCIF/PLATON results

No syntax errors found




Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.868     1.000
            Tmin(prime) and Tmax expected:      0.959     0.970
            RR(prime) =      0.879
            Please check that your absorption correction is appropriate.
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         40 Perc.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.88
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.97


   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check
Comment top

Our recent work on the x-ray structural studies of simple substituted carbazoles (Gunaseelan et al., 2007 a, b & c; Thiruvalluvar et al., 2007) directed us towards the structural studies of heterofused carbazoles (Gunaseelan et al., 2007). The hetero-ring fused carbazoles have found an important place in the medicinal chemistry because of their high pharmacological properties (Hedin et al., 2000, Hirata et al., 1999, Haider et al., 1998, Knolker & Reddy, 2002). The study of three dimensional arrangement of such compounds will provide some valuable information on synthetic as well as structure activity relationship (SAR) studies (Knolker & Reddy, 2002, Di Fabio et al., 2006). In view of these discussions, here, we present the crystal structure of such a heterofused carbazole, the title compound, (I).

The molecular structure of (I), with atomic numbering scheme, is shown in Fig. 1. The heterofused carbazole unit is planar. The planar pyrazole ring forms dihedral angles of 1.08 (7)°, 0.64 (6)° and 2.60 (7)° with pyrrole, fused benzene and methyl substituted benzene ring, respectively. The methyl group at position 3 is disordered over two positions. In the crystal structure, the molecules are stabilized by intermolecular N—H···N (-x + 1, y - 1/2, -z + 1/2) hydrogen bonds (see Fig. 2).

Related literature top

For related literature, see: Di Fabio et al. (2006); Gunaseelan et al. (2007a,b,c); Gunaseelan et al. (2007); Haider et al. (1998); Hedin et al. (2000); Hirata et al. (1999); Knolker & Reddy (2002); Thiruvalluvar et al. (2007).

Experimental top

Hydrazine hydrate (0.1 ml, 0.002 mol) was added to the solution of 2-acetyl-2,3,4,9-tetrahydro-1H-carbazol-1-one (240 mg, 0.001 mol) in glacial acetic acid (15 ml) and refluxed on oil bath for 1 h. The reaction was monitored by thin-layer chromatography. After the completion of the reaction it was poured into crushed ice. The precipitate was filtered, washed with water and dried to get the brown residue of crude compound (I), which was purified as a white powder by column chromatography over silica gel using petroleum ether-ethyl acetate (98:2 v/v) as eluant (50 mg, 20%) and recrystallized from glacial acetic.

Refinement top

H atoms bonded to N1 and N10 were located in a difference Fourier map and refined isotropically. Other H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.94–0.97 Å and Uiso(H) = 1.2–1.5 times Ueq(C). The methyl group at position 3 was found to be disordered over two positions.

Structure description top

Our recent work on the x-ray structural studies of simple substituted carbazoles (Gunaseelan et al., 2007 a, b & c; Thiruvalluvar et al., 2007) directed us towards the structural studies of heterofused carbazoles (Gunaseelan et al., 2007). The hetero-ring fused carbazoles have found an important place in the medicinal chemistry because of their high pharmacological properties (Hedin et al., 2000, Hirata et al., 1999, Haider et al., 1998, Knolker & Reddy, 2002). The study of three dimensional arrangement of such compounds will provide some valuable information on synthetic as well as structure activity relationship (SAR) studies (Knolker & Reddy, 2002, Di Fabio et al., 2006). In view of these discussions, here, we present the crystal structure of such a heterofused carbazole, the title compound, (I).

The molecular structure of (I), with atomic numbering scheme, is shown in Fig. 1. The heterofused carbazole unit is planar. The planar pyrazole ring forms dihedral angles of 1.08 (7)°, 0.64 (6)° and 2.60 (7)° with pyrrole, fused benzene and methyl substituted benzene ring, respectively. The methyl group at position 3 is disordered over two positions. In the crystal structure, the molecules are stabilized by intermolecular N—H···N (-x + 1, y - 1/2, -z + 1/2) hydrogen bonds (see Fig. 2).

For related literature, see: Di Fabio et al. (2006); Gunaseelan et al. (2007a,b,c); Gunaseelan et al. (2007); Haider et al. (1998); Hedin et al. (2000); Hirata et al. (1999); Knolker & Reddy (2002); Thiruvalluvar et al. (2007).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. The molecular packing of (I), viewed down the b axis. Dashed lines indicate hydrogen bonds. Symmetry code for both a and b: -x + 1, y - 1/2, -z + 1/2
1,10-Dihydro-3,9-dimethylpyrazolo[3,4-a]carbazole top
Crystal data top
C15H13N3F(000) = 496
Mr = 235.28Dx = 1.319 Mg m−3
Monoclinic, P21/cMelting point: 416(1) K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 11.6553 (8) ÅCell parameters from 2712 reflections
b = 5.7418 (3) Åθ = 4.8–32.4°
c = 18.0804 (12) ŵ = 0.08 mm−1
β = 101.796 (6)°T = 203 K
V = 1184.43 (13) Å3Plate, light_brown
Z = 40.51 × 0.43 × 0.37 mm
Data collection top
Oxford Diffraction Gemini
diffractometer		3939 independent reflections
Radiation source: fine-focus sealed tube1587 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
Detector resolution: 10.5081 pixels mm-1θmax = 32.4°, θmin = 4.8°
φ and ω scansh = −16→12
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)		k = −8→8
Tmin = 0.868, Tmax = 1.000l = −26→27
11247 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 0.81 w = 1/[σ2(Fo2) + (0.045P)2]
where P = (Fo2 + 2Fc2)/3
3939 reflections(Δ/σ)max < 0.001
172 parametersΔρmax = 0.18 e Å−3
0 restraintsΔρmin = −0.21 e Å−3
Crystal data top
C15H13N3V = 1184.43 (13) Å3
Mr = 235.28Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.6553 (8) ŵ = 0.08 mm−1
b = 5.7418 (3) ÅT = 203 K
c = 18.0804 (12) Å0.51 × 0.43 × 0.37 mm
β = 101.796 (6)°
Data collection top
Oxford Diffraction Gemini
diffractometer		3939 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)		1587 reflections with I > 2σ(I)
Tmin = 0.868, Tmax = 1.000Rint = 0.047
11247 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 0.81Δρmax = 0.18 e Å−3
3939 reflectionsΔρmin = −0.21 e Å−3
172 parameters
Special details top

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 > 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
xyzUiso*/UeqOcc. (<1)
N10.43672 (9)0.39900 (18)0.20431 (6)0.0308 (4)
N20.47899 (9)0.57711 (17)0.16614 (5)0.0313 (3)
N100.28403 (9)−0.04257 (18)0.23365 (6)0.0301 (3)
C30.41609 (11)0.5733 (2)0.09612 (6)0.0289 (4)
C3A0.33286 (10)0.3874 (2)0.08653 (6)0.0273 (4)
C40.24616 (11)0.2997 (2)0.02588 (6)0.0321 (4)
C50.18152 (11)0.1101 (2)0.03769 (6)0.0324 (4)
C5A0.19858 (10)0.0022 (2)0.10985 (6)0.0283 (4)
C5B0.14567 (10)−0.1954 (2)0.13948 (6)0.0300 (4)
C60.05963 (11)−0.3574 (2)0.10872 (7)0.0377 (4)
C70.03272 (12)−0.5330 (2)0.15464 (8)0.0426 (5)
C80.09011 (12)−0.5508 (2)0.22997 (8)0.0417 (5)
C90.17617 (11)−0.3965 (2)0.26261 (7)0.0344 (4)
C9A0.20113 (10)−0.2182 (2)0.21583 (7)0.0291 (4)
C10A0.28287 (10)0.0885 (2)0.16958 (6)0.0261 (4)
C110.35017 (10)0.2806 (2)0.15764 (6)0.0263 (4)
C310.43731 (12)0.7499 (2)0.03983 (7)0.0374 (4)
C910.24276 (13)−0.4178 (3)0.34279 (7)0.0503 (6)
H10.4739 (12)0.358 (2)0.2515 (7)0.048 (4)*
H40.233510.37154−0.021810.0385*
H50.124980.05020−0.002440.0388*
H60.02084−0.347170.057860.0452*
H7−0.02538−0.642370.134660.0510*
H80.06942−0.672350.259540.0500*
H100.3347 (13)−0.015 (2)0.2779 (7)0.053 (4)*
H31A0.499750.853900.063350.0560*0.500
H31B0.366260.838880.022150.0560*0.500
H31C0.459690.67151−0.002610.0560*0.500
H31D0.384050.72230−0.008090.0560*0.500
H31E0.517540.737320.033110.0560*0.500
H31F0.424110.904680.057870.0560*0.500
H91A0.21018−0.544020.367620.0754*
H91B0.23653−0.273220.369460.0754*
H91C0.32456−0.449830.343050.0754*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0319 (6)0.0337 (7)0.0245 (6)−0.0023 (5)0.0006 (5)0.0018 (5)
N20.0321 (6)0.0309 (6)0.0301 (6)−0.0016 (5)0.0043 (5)0.0025 (5)
N100.0270 (6)0.0348 (6)0.0274 (6)−0.0005 (5)0.0027 (5)0.0021 (5)
C30.0299 (7)0.0297 (7)0.0273 (7)0.0069 (6)0.0060 (5)0.0003 (6)
C3A0.0276 (7)0.0287 (7)0.0259 (6)0.0058 (6)0.0059 (5)−0.0022 (5)
C40.0340 (7)0.0383 (8)0.0221 (6)0.0067 (7)0.0016 (5)−0.0004 (6)
C50.0293 (7)0.0367 (8)0.0283 (7)0.0027 (6)−0.0008 (5)−0.0057 (6)
C5A0.0258 (7)0.0289 (7)0.0291 (7)0.0049 (6)0.0029 (5)−0.0031 (6)
C5B0.0244 (7)0.0298 (7)0.0360 (7)0.0024 (6)0.0066 (5)−0.0049 (6)
C60.0289 (7)0.0399 (8)0.0426 (8)0.0008 (6)0.0037 (6)−0.0087 (7)
C70.0336 (8)0.0353 (8)0.0606 (10)−0.0067 (7)0.0139 (7)−0.0103 (7)
C80.0370 (8)0.0338 (8)0.0595 (10)0.0011 (7)0.0219 (7)0.0033 (7)
C90.0313 (7)0.0329 (8)0.0419 (8)0.0032 (6)0.0143 (6)0.0029 (6)
C9A0.0253 (7)0.0289 (7)0.0340 (7)0.0035 (6)0.0083 (5)−0.0020 (6)
C10A0.0269 (7)0.0273 (7)0.0241 (6)0.0048 (6)0.0049 (5)−0.0001 (5)
C110.0246 (6)0.0288 (7)0.0245 (6)0.0035 (6)0.0024 (5)−0.0033 (6)
C310.0419 (8)0.0352 (8)0.0359 (7)0.0020 (7)0.0100 (6)0.0042 (6)
C910.0505 (10)0.0557 (10)0.0467 (9)0.0045 (8)0.0147 (7)0.0151 (7)
Geometric parameters (Å, º) top
N1—N21.3798 (14)C8—C91.3774 (18)
N1—C111.3579 (16)C9—C9A1.3960 (17)
N2—C31.3271 (14)C9—C911.5030 (18)
N10—C9A1.3882 (16)C10A—C111.3956 (16)
N10—C10A1.3792 (15)C4—H40.9400
N1—H10.906 (13)C5—H50.9400
N10—H100.906 (13)C6—H60.9400
C3—C3A1.4289 (17)C7—H70.9400
C3—C311.4927 (17)C8—H80.9400
C3A—C41.4227 (16)C31—H31A0.9700
C3A—C111.4013 (15)C31—H31B0.9700
C4—C51.3653 (17)C31—H31C0.9700
C5—C5A1.4211 (15)C31—H31D0.9700
C5A—C5B1.4456 (16)C31—H31E0.9700
C5A—C10A1.3940 (16)C31—H31F0.9700
C5B—C61.3972 (17)C91—H91A0.9700
C5B—C9A1.4056 (16)C91—H91B0.9700
C6—C71.3823 (18)C91—H91C0.9700
C7—C81.393 (2)
N1···N103.2036 (15)C10A···H31Fiv3.0400
N1···N2i2.9878 (14)C11···H31Fiv3.0500
N1···N10ii3.2360 (15)C31···H31Cv2.8400
N2···N10ii3.0558 (15)C91···H102.896 (13)
N2···N1ii2.9878 (14)C91···H7vii3.0800
N10···N1i3.2360 (15)C91···H31Dviii3.0700
N10···N13.2036 (15)H1···N1i2.886 (12)
N10···N2i3.0558 (15)H1···N2i2.188 (12)
N1···H10ii2.664 (15)H1···N10ii2.837 (14)
N1···H1ii2.886 (12)H1···H10ii2.51 (2)
N2···H1ii2.188 (12)H5···H6vi2.4700
N2···H10ii2.263 (15)H6···C5vi2.9600
N10···H91B2.9400H6···H5vi2.4700
N10···H1i2.837 (14)H7···C91ix3.0800
C3···C5Aiii3.5792 (17)H7···H91Bix2.5600
C3A···C5Biii3.5027 (17)H8···H91A2.4000
C4···C6iii3.4897 (18)H8···C7ix2.9800
C5A···C31iv3.5894 (18)H8···C8ix2.8900
C5A···C7iii3.4865 (17)H8···C9ix3.0900
C5A···C3iv3.5792 (17)H10···C912.896 (13)
C5B···C3Aiv3.5027 (17)H10···N1i2.664 (15)
C6···C4iv3.4897 (18)H10···N2i2.263 (15)
C7···C5Aiv3.4865 (17)H10···H1i2.51 (2)
C8···C10Aiv3.3959 (18)H31B···C4iii3.0000
C9···C11iv3.5674 (17)H31B···C5iii2.7200
C10A···C8iii3.3959 (18)H31B···C5Aiii2.9100
C11···C9iii3.5674 (17)H31C···C3v2.8200
C31···C5Aiii3.5894 (18)H31C···C31v2.8400
C3···H31Cv2.8200H31D···C43.0400
C3A···H31Fiv3.0500H31D···C91x3.0700
C4···H31Fiv3.0500H31D···H91Bx2.5300
C4···H31Biv3.0000H31F···C3Aiii3.0500
C4···H31D3.0400H31F···C4iii3.0500
C5···H31Biv2.7200H31F···C5iii3.0200
C5···H6vi2.9600H31F···C5Aiii3.0200
C5···H31Fiv3.0200H31F···C10Aiii3.0400
C5A···H31Fiv3.0200H31F···C11iii3.0500
C5A···H31Biv2.9100H91A···H82.4000
C7···H8vii2.9800H91B···N102.9400
C8···H8vii2.8900H91B···H7vii2.5600
C9···H8vii3.0900H91B···H31Dviii2.5300
N2—N1—C11110.86 (10)C5—C4—H4120.00
N1—N2—C3106.31 (10)C4—C5—H5120.00
C9A—N10—C10A108.34 (10)C5A—C5—H5120.00
C11—N1—H1127.4 (8)C5B—C6—H6121.00
N2—N1—H1120.9 (8)C7—C6—H6121.00
C9A—N10—H10129.0 (8)C6—C7—H7119.00
C10A—N10—H10122.6 (8)C8—C7—H7119.00
N2—C3—C31120.20 (11)C7—C8—H8119.00
C3A—C3—C31128.88 (10)C9—C8—H8119.00
N2—C3—C3A110.92 (10)C3—C31—H31A109.00
C3—C3A—C11104.40 (10)C3—C31—H31B109.00
C4—C3A—C11119.91 (11)C3—C31—H31C109.00
C3—C3A—C4135.69 (10)C3—C31—H31D109.00
C3A—C4—C5119.30 (10)C3—C31—H31E109.00
C4—C5—C5A120.87 (10)C3—C31—H31F109.00
C5—C5A—C5B133.80 (11)H31A—C31—H31B109.00
C5—C5A—C10A120.03 (11)H31A—C31—H31C109.00
C5B—C5A—C10A106.16 (9)H31A—C31—H31D141.00
C5A—C5B—C9A106.96 (10)H31A—C31—H31E56.00
C6—C5B—C9A118.52 (11)H31A—C31—H31F56.00
C5A—C5B—C6134.50 (10)H31B—C31—H31C109.00
C5B—C6—C7118.62 (11)H31B—C31—H31D56.00
C6—C7—C8121.21 (12)H31B—C31—H31E141.00
C7—C8—C9122.26 (12)H31B—C31—H31F56.00
C8—C9—C91123.24 (12)H31C—C31—H31D56.00
C9A—C9—C91120.90 (12)H31C—C31—H31E56.00
C8—C9—C9A115.84 (12)H31C—C31—H31F141.00
N10—C9A—C5B108.59 (10)H31D—C31—H31E109.00
N10—C9A—C9127.84 (11)H31D—C31—H31F109.00
C5B—C9A—C9123.53 (11)H31E—C31—H31F109.00
N10—C10A—C5A109.94 (10)C9—C91—H91A109.00
N10—C10A—C11130.68 (10)C9—C91—H91B109.00
C5A—C10A—C11119.37 (10)C9—C91—H91C109.00
N1—C11—C10A132.01 (10)H91A—C91—H91B109.00
C3A—C11—C10A120.51 (10)H91A—C91—H91C109.00
N1—C11—C3A107.48 (10)H91B—C91—H91C109.00
C3A—C4—H4120.00
C11—N1—N2—C31.77 (13)C10A—C5A—C5B—C6−178.14 (13)
N2—N1—C11—C3A−1.32 (13)C10A—C5A—C5B—C9A−0.06 (14)
N2—N1—C11—C10A179.04 (12)C5—C5A—C10A—N10−179.96 (11)
N1—N2—C3—C3A−1.52 (13)C5—C5A—C10A—C11−0.21 (17)
N1—N2—C3—C31178.28 (11)C5B—C5A—C10A—N10−0.44 (13)
C10A—N10—C9A—C5B−0.82 (13)C5B—C5A—C10A—C11179.31 (11)
C10A—N10—C9A—C9177.07 (12)C5A—C5B—C6—C7177.92 (13)
C9A—N10—C10A—C5A0.79 (14)C9A—C5B—C6—C70.00 (19)
C9A—N10—C10A—C11−178.93 (12)C5A—C5B—C9A—N100.54 (13)
N2—C3—C3A—C4−179.12 (13)C5A—C5B—C9A—C9−177.46 (11)
N2—C3—C3A—C110.74 (14)C6—C5B—C9A—N10178.97 (11)
C31—C3—C3A—C41.1 (2)C6—C5B—C9A—C90.97 (18)
C31—C3—C3A—C11−179.03 (12)C5B—C6—C7—C8−0.41 (19)
C3—C3A—C4—C5179.16 (13)C6—C7—C8—C9−0.1 (2)
C11—C3A—C4—C5−0.69 (18)C7—C8—C9—C9A1.05 (19)
C3—C3A—C11—N10.36 (13)C7—C8—C9—C91−177.40 (13)
C3—C3A—C11—C10A−179.94 (12)C8—C9—C9A—N10−179.07 (12)
C4—C3A—C11—N1−179.75 (11)C8—C9—C9A—C5B−1.48 (18)
C4—C3A—C11—C10A−0.06 (18)C91—C9—C9A—N10−0.6 (2)
C3A—C4—C5—C5A0.98 (18)C91—C9—C9A—C5B177.01 (12)
C4—C5—C5A—C5B−179.90 (13)N10—C10A—C11—N1−0.2 (2)
C4—C5—C5A—C10A−0.54 (18)N10—C10A—C11—C3A−179.81 (12)
C5—C5A—C5B—C61.3 (2)C5A—C10A—C11—N1−179.90 (12)
C5—C5A—C5B—C9A179.36 (13)C5A—C10A—C11—C3A0.49 (17)
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) x, y+1, z; (iv) x, y−1, z; (v) −x+1, −y+1, −z; (vi) −x, −y, −z; (vii) −x, y+1/2, −z+1/2; (viii) x, −y+1/2, z+1/2; (ix) −x, y−1/2, −z+1/2; (x) x, −y+1/2, z−1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N2i0.906 (13)2.188 (12)2.9878 (14)147.0 (10)
N10—H10···N2i0.906 (13)2.263 (15)3.0558 (15)145.9 (12)
Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formulaC15H13N3
Mr235.28
Crystal system, space groupMonoclinic, P21/c
Temperature (K)203
a, b, c (Å)11.6553 (8), 5.7418 (3), 18.0804 (12)
β (°) 101.796 (6)
V (Å3)1184.43 (13)
Z4
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.51 × 0.43 × 0.37
Data collection
DiffractometerOxford Diffraction Gemini
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2007)
Tmin, Tmax0.868, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		11247, 3939, 1587
Rint0.047
(sin θ/λ)max (Å−1)0.755
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.096, 0.81
No. of reflections3939
No. of parameters172
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.18, −0.21

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), CrysAlis RED, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N2i0.906 (13)2.188 (12)2.9878 (14)147.0 (10)
N10—H10···N2i0.906 (13)2.263 (15)3.0558 (15)145.9 (12)
Symmetry code: (i) −x+1, y−1/2, −z+1/2.
 

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