Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680703351X/bq2027sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680703351X/bq2027Isup2.hkl |
CCDC reference: 657744
Key indicators
- Single-crystal X-ray study
- T = 203 K
- Mean (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
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.
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.
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).
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).
C15H13N3 | F(000) = 496 |
Mr = 235.28 | Dx = 1.319 Mg m−3 |
Monoclinic, P21/c | Melting point: 416(1) K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 11.6553 (8) Å | Cell parameters from 2712 reflections |
b = 5.7418 (3) Å | θ = 4.8–32.4° |
c = 18.0804 (12) Å | µ = 0.08 mm−1 |
β = 101.796 (6)° | T = 203 K |
V = 1184.43 (13) Å3 | Plate, light_brown |
Z = 4 | 0.51 × 0.43 × 0.37 mm |
Oxford Diffraction Gemini diffractometer | 3939 independent reflections |
Radiation source: fine-focus sealed tube | 1587 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
Detector resolution: 10.5081 pixels mm-1 | θmax = 32.4°, θmin = 4.8° |
φ and ω scans | h = −16→12 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | k = −8→8 |
Tmin = 0.868, Tmax = 1.000 | l = −26→27 |
11247 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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.096 | H 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 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C15H13N3 | V = 1184.43 (13) Å3 |
Mr = 235.28 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.6553 (8) Å | µ = 0.08 mm−1 |
b = 5.7418 (3) Å | T = 203 K |
c = 18.0804 (12) Å | 0.51 × 0.43 × 0.37 mm |
β = 101.796 (6)° |
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 = 1.000 | Rint = 0.047 |
11247 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.096 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.81 | Δρmax = 0.18 e Å−3 |
3939 reflections | Δρmin = −0.21 e Å−3 |
172 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1 | 0.43672 (9) | 0.39900 (18) | 0.20431 (6) | 0.0308 (4) | |
N2 | 0.47899 (9) | 0.57711 (17) | 0.16614 (5) | 0.0313 (3) | |
N10 | 0.28403 (9) | −0.04257 (18) | 0.23365 (6) | 0.0301 (3) | |
C3 | 0.41609 (11) | 0.5733 (2) | 0.09612 (6) | 0.0289 (4) | |
C3A | 0.33286 (10) | 0.3874 (2) | 0.08653 (6) | 0.0273 (4) | |
C4 | 0.24616 (11) | 0.2997 (2) | 0.02588 (6) | 0.0321 (4) | |
C5 | 0.18152 (11) | 0.1101 (2) | 0.03769 (6) | 0.0324 (4) | |
C5A | 0.19858 (10) | 0.0022 (2) | 0.10985 (6) | 0.0283 (4) | |
C5B | 0.14567 (10) | −0.1954 (2) | 0.13948 (6) | 0.0300 (4) | |
C6 | 0.05963 (11) | −0.3574 (2) | 0.10872 (7) | 0.0377 (4) | |
C7 | 0.03272 (12) | −0.5330 (2) | 0.15464 (8) | 0.0426 (5) | |
C8 | 0.09011 (12) | −0.5508 (2) | 0.22997 (8) | 0.0417 (5) | |
C9 | 0.17617 (11) | −0.3965 (2) | 0.26261 (7) | 0.0344 (4) | |
C9A | 0.20113 (10) | −0.2182 (2) | 0.21583 (7) | 0.0291 (4) | |
C10A | 0.28287 (10) | 0.0885 (2) | 0.16958 (6) | 0.0261 (4) | |
C11 | 0.35017 (10) | 0.2806 (2) | 0.15764 (6) | 0.0263 (4) | |
C31 | 0.43731 (12) | 0.7499 (2) | 0.03983 (7) | 0.0374 (4) | |
C91 | 0.24276 (13) | −0.4178 (3) | 0.34279 (7) | 0.0503 (6) | |
H1 | 0.4739 (12) | 0.358 (2) | 0.2515 (7) | 0.048 (4)* | |
H4 | 0.23351 | 0.37154 | −0.02181 | 0.0385* | |
H5 | 0.12498 | 0.05020 | −0.00244 | 0.0388* | |
H6 | 0.02084 | −0.34717 | 0.05786 | 0.0452* | |
H7 | −0.02538 | −0.64237 | 0.13466 | 0.0510* | |
H8 | 0.06942 | −0.67235 | 0.25954 | 0.0500* | |
H10 | 0.3347 (13) | −0.015 (2) | 0.2779 (7) | 0.053 (4)* | |
H31A | 0.49975 | 0.85390 | 0.06335 | 0.0560* | 0.500 |
H31B | 0.36626 | 0.83888 | 0.02215 | 0.0560* | 0.500 |
H31C | 0.45969 | 0.67151 | −0.00261 | 0.0560* | 0.500 |
H31D | 0.38405 | 0.72230 | −0.00809 | 0.0560* | 0.500 |
H31E | 0.51754 | 0.73732 | 0.03311 | 0.0560* | 0.500 |
H31F | 0.42411 | 0.90468 | 0.05787 | 0.0560* | 0.500 |
H91A | 0.21018 | −0.54402 | 0.36762 | 0.0754* | |
H91B | 0.23653 | −0.27322 | 0.36946 | 0.0754* | |
H91C | 0.32456 | −0.44983 | 0.34305 | 0.0754* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0319 (6) | 0.0337 (7) | 0.0245 (6) | −0.0023 (5) | 0.0006 (5) | 0.0018 (5) |
N2 | 0.0321 (6) | 0.0309 (6) | 0.0301 (6) | −0.0016 (5) | 0.0043 (5) | 0.0025 (5) |
N10 | 0.0270 (6) | 0.0348 (6) | 0.0274 (6) | −0.0005 (5) | 0.0027 (5) | 0.0021 (5) |
C3 | 0.0299 (7) | 0.0297 (7) | 0.0273 (7) | 0.0069 (6) | 0.0060 (5) | 0.0003 (6) |
C3A | 0.0276 (7) | 0.0287 (7) | 0.0259 (6) | 0.0058 (6) | 0.0059 (5) | −0.0022 (5) |
C4 | 0.0340 (7) | 0.0383 (8) | 0.0221 (6) | 0.0067 (7) | 0.0016 (5) | −0.0004 (6) |
C5 | 0.0293 (7) | 0.0367 (8) | 0.0283 (7) | 0.0027 (6) | −0.0008 (5) | −0.0057 (6) |
C5A | 0.0258 (7) | 0.0289 (7) | 0.0291 (7) | 0.0049 (6) | 0.0029 (5) | −0.0031 (6) |
C5B | 0.0244 (7) | 0.0298 (7) | 0.0360 (7) | 0.0024 (6) | 0.0066 (5) | −0.0049 (6) |
C6 | 0.0289 (7) | 0.0399 (8) | 0.0426 (8) | 0.0008 (6) | 0.0037 (6) | −0.0087 (7) |
C7 | 0.0336 (8) | 0.0353 (8) | 0.0606 (10) | −0.0067 (7) | 0.0139 (7) | −0.0103 (7) |
C8 | 0.0370 (8) | 0.0338 (8) | 0.0595 (10) | 0.0011 (7) | 0.0219 (7) | 0.0033 (7) |
C9 | 0.0313 (7) | 0.0329 (8) | 0.0419 (8) | 0.0032 (6) | 0.0143 (6) | 0.0029 (6) |
C9A | 0.0253 (7) | 0.0289 (7) | 0.0340 (7) | 0.0035 (6) | 0.0083 (5) | −0.0020 (6) |
C10A | 0.0269 (7) | 0.0273 (7) | 0.0241 (6) | 0.0048 (6) | 0.0049 (5) | −0.0001 (5) |
C11 | 0.0246 (6) | 0.0288 (7) | 0.0245 (6) | 0.0035 (6) | 0.0024 (5) | −0.0033 (6) |
C31 | 0.0419 (8) | 0.0352 (8) | 0.0359 (7) | 0.0020 (7) | 0.0100 (6) | 0.0042 (6) |
C91 | 0.0505 (10) | 0.0557 (10) | 0.0467 (9) | 0.0045 (8) | 0.0147 (7) | 0.0151 (7) |
N1—N2 | 1.3798 (14) | C8—C9 | 1.3774 (18) |
N1—C11 | 1.3579 (16) | C9—C9A | 1.3960 (17) |
N2—C3 | 1.3271 (14) | C9—C91 | 1.5030 (18) |
N10—C9A | 1.3882 (16) | C10A—C11 | 1.3956 (16) |
N10—C10A | 1.3792 (15) | C4—H4 | 0.9400 |
N1—H1 | 0.906 (13) | C5—H5 | 0.9400 |
N10—H10 | 0.906 (13) | C6—H6 | 0.9400 |
C3—C3A | 1.4289 (17) | C7—H7 | 0.9400 |
C3—C31 | 1.4927 (17) | C8—H8 | 0.9400 |
C3A—C4 | 1.4227 (16) | C31—H31A | 0.9700 |
C3A—C11 | 1.4013 (15) | C31—H31B | 0.9700 |
C4—C5 | 1.3653 (17) | C31—H31C | 0.9700 |
C5—C5A | 1.4211 (15) | C31—H31D | 0.9700 |
C5A—C5B | 1.4456 (16) | C31—H31E | 0.9700 |
C5A—C10A | 1.3940 (16) | C31—H31F | 0.9700 |
C5B—C6 | 1.3972 (17) | C91—H91A | 0.9700 |
C5B—C9A | 1.4056 (16) | C91—H91B | 0.9700 |
C6—C7 | 1.3823 (18) | C91—H91C | 0.9700 |
C7—C8 | 1.393 (2) | ||
N1···N10 | 3.2036 (15) | C10A···H31Fiv | 3.0400 |
N1···N2i | 2.9878 (14) | C11···H31Fiv | 3.0500 |
N1···N10ii | 3.2360 (15) | C31···H31Cv | 2.8400 |
N2···N10ii | 3.0558 (15) | C91···H10 | 2.896 (13) |
N2···N1ii | 2.9878 (14) | C91···H7vii | 3.0800 |
N10···N1i | 3.2360 (15) | C91···H31Dviii | 3.0700 |
N10···N1 | 3.2036 (15) | H1···N1i | 2.886 (12) |
N10···N2i | 3.0558 (15) | H1···N2i | 2.188 (12) |
N1···H10ii | 2.664 (15) | H1···N10ii | 2.837 (14) |
N1···H1ii | 2.886 (12) | H1···H10ii | 2.51 (2) |
N2···H1ii | 2.188 (12) | H5···H6vi | 2.4700 |
N2···H10ii | 2.263 (15) | H6···C5vi | 2.9600 |
N10···H91B | 2.9400 | H6···H5vi | 2.4700 |
N10···H1i | 2.837 (14) | H7···C91ix | 3.0800 |
C3···C5Aiii | 3.5792 (17) | H7···H91Bix | 2.5600 |
C3A···C5Biii | 3.5027 (17) | H8···H91A | 2.4000 |
C4···C6iii | 3.4897 (18) | H8···C7ix | 2.9800 |
C5A···C31iv | 3.5894 (18) | H8···C8ix | 2.8900 |
C5A···C7iii | 3.4865 (17) | H8···C9ix | 3.0900 |
C5A···C3iv | 3.5792 (17) | H10···C91 | 2.896 (13) |
C5B···C3Aiv | 3.5027 (17) | H10···N1i | 2.664 (15) |
C6···C4iv | 3.4897 (18) | H10···N2i | 2.263 (15) |
C7···C5Aiv | 3.4865 (17) | H10···H1i | 2.51 (2) |
C8···C10Aiv | 3.3959 (18) | H31B···C4iii | 3.0000 |
C9···C11iv | 3.5674 (17) | H31B···C5iii | 2.7200 |
C10A···C8iii | 3.3959 (18) | H31B···C5Aiii | 2.9100 |
C11···C9iii | 3.5674 (17) | H31C···C3v | 2.8200 |
C31···C5Aiii | 3.5894 (18) | H31C···C31v | 2.8400 |
C3···H31Cv | 2.8200 | H31D···C4 | 3.0400 |
C3A···H31Fiv | 3.0500 | H31D···C91x | 3.0700 |
C4···H31Fiv | 3.0500 | H31D···H91Bx | 2.5300 |
C4···H31Biv | 3.0000 | H31F···C3Aiii | 3.0500 |
C4···H31D | 3.0400 | H31F···C4iii | 3.0500 |
C5···H31Biv | 2.7200 | H31F···C5iii | 3.0200 |
C5···H6vi | 2.9600 | H31F···C5Aiii | 3.0200 |
C5···H31Fiv | 3.0200 | H31F···C10Aiii | 3.0400 |
C5A···H31Fiv | 3.0200 | H31F···C11iii | 3.0500 |
C5A···H31Biv | 2.9100 | H91A···H8 | 2.4000 |
C7···H8vii | 2.9800 | H91B···N10 | 2.9400 |
C8···H8vii | 2.8900 | H91B···H7vii | 2.5600 |
C9···H8vii | 3.0900 | H91B···H31Dviii | 2.5300 |
N2—N1—C11 | 110.86 (10) | C5—C4—H4 | 120.00 |
N1—N2—C3 | 106.31 (10) | C4—C5—H5 | 120.00 |
C9A—N10—C10A | 108.34 (10) | C5A—C5—H5 | 120.00 |
C11—N1—H1 | 127.4 (8) | C5B—C6—H6 | 121.00 |
N2—N1—H1 | 120.9 (8) | C7—C6—H6 | 121.00 |
C9A—N10—H10 | 129.0 (8) | C6—C7—H7 | 119.00 |
C10A—N10—H10 | 122.6 (8) | C8—C7—H7 | 119.00 |
N2—C3—C31 | 120.20 (11) | C7—C8—H8 | 119.00 |
C3A—C3—C31 | 128.88 (10) | C9—C8—H8 | 119.00 |
N2—C3—C3A | 110.92 (10) | C3—C31—H31A | 109.00 |
C3—C3A—C11 | 104.40 (10) | C3—C31—H31B | 109.00 |
C4—C3A—C11 | 119.91 (11) | C3—C31—H31C | 109.00 |
C3—C3A—C4 | 135.69 (10) | C3—C31—H31D | 109.00 |
C3A—C4—C5 | 119.30 (10) | C3—C31—H31E | 109.00 |
C4—C5—C5A | 120.87 (10) | C3—C31—H31F | 109.00 |
C5—C5A—C5B | 133.80 (11) | H31A—C31—H31B | 109.00 |
C5—C5A—C10A | 120.03 (11) | H31A—C31—H31C | 109.00 |
C5B—C5A—C10A | 106.16 (9) | H31A—C31—H31D | 141.00 |
C5A—C5B—C9A | 106.96 (10) | H31A—C31—H31E | 56.00 |
C6—C5B—C9A | 118.52 (11) | H31A—C31—H31F | 56.00 |
C5A—C5B—C6 | 134.50 (10) | H31B—C31—H31C | 109.00 |
C5B—C6—C7 | 118.62 (11) | H31B—C31—H31D | 56.00 |
C6—C7—C8 | 121.21 (12) | H31B—C31—H31E | 141.00 |
C7—C8—C9 | 122.26 (12) | H31B—C31—H31F | 56.00 |
C8—C9—C91 | 123.24 (12) | H31C—C31—H31D | 56.00 |
C9A—C9—C91 | 120.90 (12) | H31C—C31—H31E | 56.00 |
C8—C9—C9A | 115.84 (12) | H31C—C31—H31F | 141.00 |
N10—C9A—C5B | 108.59 (10) | H31D—C31—H31E | 109.00 |
N10—C9A—C9 | 127.84 (11) | H31D—C31—H31F | 109.00 |
C5B—C9A—C9 | 123.53 (11) | H31E—C31—H31F | 109.00 |
N10—C10A—C5A | 109.94 (10) | C9—C91—H91A | 109.00 |
N10—C10A—C11 | 130.68 (10) | C9—C91—H91B | 109.00 |
C5A—C10A—C11 | 119.37 (10) | C9—C91—H91C | 109.00 |
N1—C11—C10A | 132.01 (10) | H91A—C91—H91B | 109.00 |
C3A—C11—C10A | 120.51 (10) | H91A—C91—H91C | 109.00 |
N1—C11—C3A | 107.48 (10) | H91B—C91—H91C | 109.00 |
C3A—C4—H4 | 120.00 | ||
C11—N1—N2—C3 | 1.77 (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—C10A | 179.04 (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—C31 | 178.28 (11) | C5B—C5A—C10A—N10 | −0.44 (13) |
C10A—N10—C9A—C5B | −0.82 (13) | C5B—C5A—C10A—C11 | 179.31 (11) |
C10A—N10—C9A—C9 | 177.07 (12) | C5A—C5B—C6—C7 | 177.92 (13) |
C9A—N10—C10A—C5A | 0.79 (14) | C9A—C5B—C6—C7 | 0.00 (19) |
C9A—N10—C10A—C11 | −178.93 (12) | C5A—C5B—C9A—N10 | 0.54 (13) |
N2—C3—C3A—C4 | −179.12 (13) | C5A—C5B—C9A—C9 | −177.46 (11) |
N2—C3—C3A—C11 | 0.74 (14) | C6—C5B—C9A—N10 | 178.97 (11) |
C31—C3—C3A—C4 | 1.1 (2) | C6—C5B—C9A—C9 | 0.97 (18) |
C31—C3—C3A—C11 | −179.03 (12) | C5B—C6—C7—C8 | −0.41 (19) |
C3—C3A—C4—C5 | 179.16 (13) | C6—C7—C8—C9 | −0.1 (2) |
C11—C3A—C4—C5 | −0.69 (18) | C7—C8—C9—C9A | 1.05 (19) |
C3—C3A—C11—N1 | 0.36 (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—C5A | 0.98 (18) | C91—C9—C9A—C5B | 177.01 (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—C6 | 1.3 (2) | C5A—C10A—C11—N1 | −179.90 (12) |
C5—C5A—C5B—C9A | 179.36 (13) | C5A—C10A—C11—C3A | 0.49 (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. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N2i | 0.906 (13) | 2.188 (12) | 2.9878 (14) | 147.0 (10) |
N10—H10···N2i | 0.906 (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 formula | C15H13N3 |
Mr | 235.28 |
Crystal system, space group | Monoclinic, 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) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.51 × 0.43 × 0.37 |
Data collection | |
Diffractometer | Oxford Diffraction Gemini |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2007) |
Tmin, Tmax | 0.868, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11247, 3939, 1587 |
Rint | 0.047 |
(sin θ/λ)max (Å−1) | 0.755 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.096, 0.81 |
No. of reflections | 3939 |
No. of parameters | 172 |
H-atom treatment | H 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).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N2i | 0.906 (13) | 2.188 (12) | 2.9878 (14) | 147.0 (10) |
N10—H10···N2i | 0.906 (13) | 2.263 (15) | 3.0558 (15) | 145.9 (12) |
Symmetry code: (i) −x+1, y−1/2, −z+1/2. |
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).