Literature DB >> 21582550

4,8-Dimethyl-pyrano[2,3-a]carbazol-2(11H)-one.

M Sridharan, K J Rajendra Prasad, A Thomas Gunaseelan, A Thiruvalluvar, R J Butcher.   

Abstract

The mol-ecule of the title compound, C(17)H(13)NO(2), is nearly planar, the r.m.s. deviation for all non-H atoms excluding the two methyl C atoms being 0.089 Å. Inter-molecular N-H⋯O and C-H⋯O hydrogen bonds are found in the crystal structure. C-H⋯π inter-actions are also found. The H atoms of the methyl group attached to the benzene ring are disordered equally over two positions.

Entities:  

Year:  2009        PMID： 21582550      PMCID： PMC2968986          DOI： 10.1107/S1600536809009854

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the synthesis of 2-methyl- and 2-phenyl-pyrano[2,3-a]carbazol-4-ones and their derivatives, see: Kavitha & Rajendra Prasad (2003 ▶). For related crystal structures, see: Sridharan et al. (2007 ▶); Sridharan et al. (2008a ▶,b ▶); Sridharan et al. (2008 ▶).

Experimental

Crystal data

C17H13NO2 M = 263.28 Monoclinic, a = 26.8502 (4) Å b = 6.8202 (1) Å c = 15.8265 (3) Å β = 115.531 (2)° V = 2615.21 (9) Å3 Z = 8 Cu Kα radiation μ = 0.71 mm−1 T = 295 K 0.48 × 0.45 × 0.18 mm

Data collection

Oxford Diffraction Gemini R diffractometer Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.313, T max = 1.000 (expected range = 0.276–0.880) 6122 measured reflections 2703 independent reflections 2218 reflections with I > 2σ(I) R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.044 wR(F 2) = 0.132 S = 1.07 2703 reflections 186 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.22 e Å−3 Δρmin = −0.18 e Å−3 Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809009854/wn2315sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009854/wn2315Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C17H13NO2F(000) = 1104
Mr = 263.28Dx = 1.337 Mg m−3
Monoclinic, C2/cMelting point: 506(1) K
Hall symbol: -C 2ycCu Kα radiation, λ = 1.54184 Å
a = 26.8502 (4) ÅCell parameters from 3727 reflections
b = 6.8202 (1) Åθ = 5.7–77.3°
c = 15.8265 (3) ŵ = 0.71 mm−1
β = 115.531 (2)°T = 295 K
V = 2615.21 (9) Å3Plate, colourless
Z = 80.48 × 0.45 × 0.18 mm
Oxford Diffraction Gemini R diffractometer2703 independent reflections
Radiation source: fine-focus sealed tube2218 reflections with I > 2σ(I)
graphiteRint = 0.018
Detector resolution: 10.5081 pixels mm-1θmax = 77.8°, θmin = 5.7°
φ and ω scansh = −33→34
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)k = −8→6
Tmin = 0.313, Tmax = 1.000l = −19→18
6122 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H atoms treated by a mixture of independent and constrained refinement
S = 1.07w = 1/[σ2(Fo2) + (0.0834P)2 + 0.3277P] where P = (Fo2 + 2Fc2)/3
2703 reflections(Δ/σ)max = 0.001
186 parametersΔρmax = 0.22 e Å−3
0 restraintsΔρmin = −0.18 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.
xyzUiso*/UeqOcc. (<1)
O10.29530 (4)1.01921 (13)0.07257 (7)0.0519 (3)
O20.35050 (5)1.19047 (16)0.03063 (9)0.0686 (4)
N110.19050 (5)0.97178 (18)0.07986 (8)0.0519 (3)
C20.34394 (6)1.0397 (2)0.06525 (10)0.0537 (4)
C30.38333 (6)0.8836 (2)0.10052 (10)0.0556 (4)
C40.37356 (5)0.7174 (2)0.13688 (9)0.0514 (4)
C4A0.32087 (5)0.69352 (19)0.13969 (9)0.0481 (4)
C50.30472 (6)0.5221 (2)0.17213 (9)0.0543 (4)
C60.25386 (6)0.5074 (2)0.17191 (9)0.0545 (4)
C6A0.21696 (5)0.6649 (2)0.13986 (9)0.0487 (4)
C6B0.16178 (6)0.7006 (2)0.12955 (9)0.0516 (4)
C70.12374 (6)0.5877 (3)0.14701 (10)0.0605 (5)
C80.07214 (6)0.6638 (3)0.12677 (11)0.0691 (5)
C90.05908 (6)0.8535 (3)0.09007 (11)0.0696 (6)
C100.09551 (6)0.9699 (3)0.07195 (11)0.0620 (5)
C10A0.14709 (5)0.8902 (2)0.09203 (9)0.0517 (4)
C11A0.23240 (5)0.83643 (18)0.10748 (9)0.0469 (4)
C11B0.28383 (5)0.84912 (18)0.10697 (8)0.0462 (4)
C140.41674 (6)0.5602 (3)0.17296 (12)0.0658 (5)
C180.02959 (8)0.5430 (4)0.14272 (16)0.0991 (9)
H30.417170.897750.098210.0667*
H50.329220.417560.194010.0651*
H60.243860.393320.192940.0653*
H70.133100.462340.172050.0726*
H90.024340.903510.077300.0835*
H100.085981.095600.047480.0744*
H110.1888 (7)1.081 (3)0.0516 (13)0.070 (5)*
H14A0.449160.602400.166910.0988*
H14B0.402810.442340.137390.0988*
H14C0.425900.535280.237690.0988*
H18A−0.003620.618180.125050.1487*0.500
H18B0.043770.508290.207720.1487*0.500
H18C0.021680.425920.105500.1487*0.500
H18D0.044840.416740.167130.1487*0.500
H18E−0.002550.526630.084460.1487*0.500
H18F0.019540.609010.186680.1487*0.500
U11U22U33U12U13U23
O10.0547 (5)0.0430 (5)0.0602 (5)−0.0053 (4)0.0269 (4)0.0030 (4)
O20.0681 (6)0.0510 (6)0.0928 (8)−0.0093 (4)0.0404 (6)0.0104 (5)
N110.0551 (6)0.0481 (6)0.0560 (6)−0.0014 (5)0.0272 (5)0.0044 (5)
C20.0561 (7)0.0484 (7)0.0580 (8)−0.0117 (6)0.0259 (6)−0.0030 (6)
C30.0475 (6)0.0582 (8)0.0595 (8)−0.0086 (6)0.0216 (6)−0.0022 (6)
C40.0502 (7)0.0539 (7)0.0453 (6)−0.0042 (5)0.0160 (5)−0.0018 (5)
C4A0.0526 (7)0.0481 (7)0.0410 (6)−0.0042 (5)0.0178 (5)0.0003 (5)
C50.0599 (8)0.0501 (7)0.0503 (7)0.0015 (6)0.0214 (6)0.0090 (5)
C60.0647 (8)0.0506 (7)0.0483 (7)−0.0050 (6)0.0246 (6)0.0095 (5)
C6A0.0554 (7)0.0514 (7)0.0405 (6)−0.0081 (5)0.0218 (5)0.0006 (5)
C6B0.0551 (7)0.0593 (8)0.0413 (6)−0.0089 (6)0.0216 (5)−0.0007 (5)
C70.0614 (8)0.0707 (9)0.0519 (7)−0.0122 (7)0.0268 (6)0.0055 (7)
C80.0588 (8)0.0958 (12)0.0556 (8)−0.0151 (8)0.0273 (7)0.0064 (8)
C90.0526 (7)0.0983 (13)0.0605 (9)0.0001 (8)0.0268 (7)0.0068 (8)
C100.0580 (8)0.0713 (9)0.0593 (8)0.0015 (7)0.0277 (6)0.0046 (7)
C10A0.0545 (7)0.0574 (7)0.0459 (6)−0.0063 (6)0.0241 (5)−0.0014 (5)
C11A0.0536 (7)0.0455 (6)0.0419 (6)−0.0041 (5)0.0208 (5)−0.0009 (5)
C11B0.0537 (7)0.0436 (6)0.0413 (6)−0.0071 (5)0.0205 (5)−0.0009 (4)
C140.0527 (7)0.0678 (9)0.0709 (9)0.0052 (7)0.0210 (7)0.0094 (7)
C180.0691 (10)0.137 (2)0.0963 (14)−0.0196 (12)0.0406 (10)0.0270 (14)
O1—C21.367 (2)C8—C181.515 (3)
O1—C11B1.3717 (16)C9—C101.382 (3)
O2—C21.2132 (18)C10—C10A1.391 (2)
N11—C10A1.378 (2)C11A—C11B1.387 (2)
N11—C11A1.3730 (19)C3—H30.9300
N11—H110.86 (2)C5—H50.9300
C2—C31.433 (2)C6—H60.9300
C3—C41.347 (2)C7—H70.9300
C4—C4A1.444 (2)C9—H90.9300
C4—C141.500 (2)C10—H100.9300
C4A—C11B1.3927 (19)C14—H14A0.9600
C4A—C51.418 (2)C14—H14B0.9600
C5—C61.368 (2)C14—H14C0.9600
C6—C6A1.400 (2)C18—H18A0.9600
C6A—C11A1.4093 (19)C18—H18B0.9600
C6A—C6B1.440 (2)C18—H18C0.9600
C6B—C71.399 (2)C18—H18D0.9600
C6B—C10A1.4066 (19)C18—H18E0.9600
C7—C81.382 (3)C18—H18F0.9600
C8—C91.400 (3)
O1···N112.8837 (19)C5···H14C2.9600
O2···N11i2.8136 (17)C5···H14B2.9600
O2···C14ii3.338 (2)C6A···H6v2.8500
O1···H112.77 (2)C6B···H5v3.0800
O2···H14Bii2.3900C9···H14Cv2.8600
O2···H10i2.9000C11A···H6v2.9700
O2···H11i2.01 (2)C14···H52.6900
N11···O12.8837 (19)C18···H3vii2.9600
N11···O2i2.8136 (17)H3···H14A2.2700
N11···C4iii3.3621 (17)H3···C18viii2.9600
C2···C6iii3.548 (2)H3···H18Aviii2.4900
C2···C6Aiii3.2532 (19)H3···H18Eviii2.4200
C2···C6Biii3.436 (2)H5···C142.6900
C3···C10Aiii3.3608 (19)H5···H14B2.5000
C3···C6Biii3.3546 (19)H5···H14C2.5100
C4···N11iii3.3621 (17)H5···C6Biv3.0800
C4···C10Aiii3.4985 (18)H6···C6Aiv2.8500
C4A···C11Aiii3.5450 (18)H6···C11Aiv2.9700
C5···C10Aiv3.5003 (18)H7···H18D2.3600
C6···C6Aiv3.5963 (19)H9···H18A2.3300
C6···C11Aiv3.5463 (19)H9···H9ix2.5800
C6···C2iii3.548 (2)H10···O2i2.9000
C6A···C6v3.5963 (19)H11···O12.77 (2)
C6A···C2iii3.2532 (19)H11···O2i2.01 (2)
C6B···C2iii3.436 (2)H11···C2i3.08 (2)
C6B···C3iii3.3546 (19)H14A···H32.2700
C10A···C4iii3.4985 (18)H14B···O2vi2.3900
C10A···C3iii3.3608 (19)H14B···C52.9600
C10A···C5v3.5003 (18)H14B···H52.5000
C11A···C6v3.5463 (19)H14C···C52.9600
C11A···C11Biii3.4692 (18)H14C···H52.5100
C11A···C4Aiii3.5450 (18)H14C···C9iv2.8600
C11B···C11Biii3.3601 (16)H18A···H92.3300
C11B···C11Aiii3.4692 (18)H18A···H3vii2.4900
C14···O2vi3.338 (2)H18B···C3iv2.9400
C2···H11i3.08 (2)H18D···H72.3600
C3···H18Bv2.9400H18E···H3vii2.4200
C2—O1—C11B120.41 (11)C4—C3—H3119.00
C10A—N11—C11A108.09 (12)C4A—C5—H5119.00
C11A—N11—H11126.9 (14)C6—C5—H5119.00
C10A—N11—H11124.3 (14)C5—C6—H6120.00
O1—C2—C3117.55 (13)C6A—C6—H6120.00
O1—C2—O2117.06 (14)C6B—C7—H7120.00
O2—C2—C3125.38 (17)C8—C7—H7120.00
C2—C3—C4122.99 (16)C8—C9—H9119.00
C4A—C4—C14120.98 (13)C10—C9—H9119.00
C3—C4—C14120.22 (15)C9—C10—H10122.00
C3—C4—C4A118.81 (13)C10A—C10—H10122.00
C4—C4A—C5124.12 (13)C4—C14—H14A109.00
C4—C4A—C11B117.05 (12)C4—C14—H14B109.00
C5—C4A—C11B118.82 (14)C4—C14—H14C109.00
C4A—C5—C6121.36 (13)H14A—C14—H14B109.00
C5—C6—C6A119.64 (13)H14A—C14—H14C109.00
C6—C6A—C11A119.71 (14)H14B—C14—H14C109.00
C6B—C6A—C11A105.55 (12)C8—C18—H18A109.00
C6—C6A—C6B134.74 (13)C8—C18—H18B109.00
C7—C6B—C10A119.59 (15)C8—C18—H18C109.00
C6A—C6B—C7133.48 (14)C8—C18—H18D109.00
C6A—C6B—C10A106.92 (13)C8—C18—H18E109.00
C6B—C7—C8119.48 (17)C8—C18—H18F109.00
C9—C8—C18119.98 (17)H18A—C18—H18B109.00
C7—C8—C18120.65 (19)H18A—C18—H18C109.00
C7—C8—C9119.36 (17)H18A—C18—H18D141.00
C8—C9—C10122.95 (17)H18A—C18—H18E56.00
C9—C10—C10A116.87 (17)H18A—C18—H18F56.00
N11—C10A—C10128.99 (14)H18B—C18—H18C109.00
N11—C10A—C6B109.27 (13)H18B—C18—H18D56.00
C6B—C10A—C10121.74 (15)H18B—C18—H18E141.00
N11—C11A—C11B129.60 (12)H18B—C18—H18F56.00
C6A—C11A—C11B120.23 (12)H18C—C18—H18D56.00
N11—C11A—C6A110.17 (13)H18C—C18—H18E56.00
C4A—C11B—C11A120.23 (12)H18C—C18—H18F141.00
O1—C11B—C4A123.06 (13)H18D—C18—H18E109.00
O1—C11B—C11A116.71 (12)H18D—C18—H18F109.00
C2—C3—H3118.00H18E—C18—H18F109.00
C11B—O1—C2—O2176.99 (12)C6—C6A—C6B—C7−1.0 (3)
C11B—O1—C2—C3−4.14 (18)C6—C6A—C6B—C10A−179.50 (15)
C2—O1—C11B—C4A2.84 (18)C11A—C6A—C6B—C7178.38 (15)
C2—O1—C11B—C11A−176.72 (12)C11A—C6A—C6B—C10A−0.12 (14)
C11A—N11—C10A—C6B0.99 (15)C6—C6A—C11A—N11−179.77 (12)
C11A—N11—C10A—C10−178.52 (14)C6—C6A—C11A—C11B0.25 (19)
C10A—N11—C11A—C6A−1.08 (15)C6B—C6A—C11A—N110.74 (15)
C10A—N11—C11A—C11B178.89 (13)C6B—C6A—C11A—C11B−179.24 (12)
O1—C2—C3—C42.4 (2)C6A—C6B—C7—C8−178.08 (15)
O2—C2—C3—C4−178.81 (15)C10A—C6B—C7—C80.3 (2)
C2—C3—C4—C4A0.7 (2)C6A—C6B—C10A—N11−0.53 (15)
C2—C3—C4—C14−179.72 (14)C6A—C6B—C10A—C10179.03 (13)
C3—C4—C4A—C5176.95 (13)C7—C6B—C10A—N11−179.27 (12)
C3—C4—C4A—C11B−2.11 (19)C7—C6B—C10A—C100.3 (2)
C14—C4—C4A—C5−2.6 (2)C6B—C7—C8—C9−0.7 (2)
C14—C4—C4A—C11B178.34 (13)C6B—C7—C8—C18178.49 (16)
C4—C4A—C5—C6−179.13 (13)C7—C8—C9—C100.6 (3)
C11B—C4A—C5—C6−0.09 (19)C18—C8—C9—C10−178.59 (17)
C4—C4A—C11B—O10.40 (18)C8—C9—C10—C10A−0.1 (2)
C4—C4A—C11B—C11A179.94 (13)C9—C10—C10A—N11179.08 (14)
C5—C4A—C11B—O1−178.72 (11)C9—C10—C10A—C6B−0.4 (2)
C5—C4A—C11B—C11A0.83 (18)N11—C11A—C11B—O1−1.3 (2)
C4A—C5—C6—C6A−0.6 (2)N11—C11A—C11B—C4A179.12 (13)
C5—C6—C6A—C6B179.79 (14)C6A—C11A—C11B—O1178.66 (11)
C5—C6—C6A—C11A0.48 (19)C6A—C11A—C11B—C4A−0.91 (19)
D—H···AD—HH···AD···AD—H···A
N11—H11···O2i0.86 (2)2.01 (2)2.814 (2)154.5 (19)
C14—H14B···O2vi0.962.393.338 (2)168
C6—H6···Cg1iv0.932.903.389 (1)114
C5—H5···Cg2iv0.932.983.626 (1)128
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N11—H11⋯O2i0.86 (2)2.01 (2)2.814 (2)154.5 (19)
C14—H14B⋯O2ii0.962.393.338 (2)168
C6—H6⋯Cg1iii0.932.903.389 (1)114
C5—H5⋯Cg2iii0.932.983.626 (1)128

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the pyrrole ring and Cg2 is the centroid of the C6B–C10A ring.

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Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

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Authors:  Makuteswaran Sridharan; Karnam J Rajendra Prasad; Aimable Ngendahimana; Matthias Zeller
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-10-22

3.  2,2,9-Trimethyl-2,3-dihydro-pyrano[2,3-a]carbazol-4-(11H)-one.

Authors:  Makuteswaran Sridharan; Karnam J Rajendra Prasad; Matthias Zeller
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-10-22

4.  2,2,10-Trimethyl-2,3-dihydro-pyrano[2,3-a]carbazol-4(11H)-one.

Authors:  Makuteswaran Sridharan; Karnam J Rajendra Prasad; Aimable Ngendahimana; Matthias Zeller
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-10-22

5.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
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1.  10-Methyl-2-oxo-4-phenyl-2,11-di-hydro-pyrano[2,3-a]carbazole-3-carbo-nitrile.

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