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The carbazole unit of the title mol­ecule, C13H13NO, is not planar. The dihedral angle between the benzene ring and the fused pyrrole ring is 2.5 (1)°. The cyclo­hexene ring is in an envelope form. There is an intra­molecular C—H...O hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807034307/ww2091sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807034307/ww2091Isup2.hkl
Contains datablock I

CCDC reference: 657788

Key indicators

  • Single-crystal X-ray study
  • T = 203 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.044
  • wR factor = 0.106
  • Data-to-parameter ratio = 10.8

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: 0.798 1.000 Tmin(prime) and Tmax expected: 0.967 0.977 RR(prime) = 0.806 Please check that your absorption correction is appropriate. PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.81 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98
Alert level G REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values From the CIF: _diffrn_reflns_theta_max 30.51 From the CIF: _reflns_number_total 1464 From the CIF: _diffrn_reflns_limit_ max hkl 10. 19. 12. From the CIF: _diffrn_reflns_limit_ min hkl 0. 0. 0. TEST1: Expected hkl limits for theta max Calculated maximum hkl 10. 21. 12. Calculated minimum hkl -10. -21. -12. REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 30.51 From the CIF: _reflns_number_total 1464 Count of symmetry unique reflns 1628 Completeness (_total/calc) 89.93% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 1 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 4 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Indole and its various substituted products have long been known for their interesting chemical and biological activities (Chandrakantha et al., 1992). The indole ring system is present in a number of natural products, many of which are found to possess pharmacological properties like anti-microbial, anti-inflammatory and anti-implantation activities (Rodriguez et al., 1985; Ebenezer Martin & Rajendra Prasad, 2006; Balamurali & Rajendra Prasad, 2001). Carbazoles formed by the fusion of indole ring with aromatic six-membered ring, are also widely used in many areas in biological sciences. The structures of these derivatives are analogous to that of ellipticine, a plant alkaloid having pronounced anti-tumour activity and are found to have DNA intercalating properties (Courseille et al., 1974). Synthetic approaches to substituted carbazoles are of special interest and contemporary importance since the growing variety of carbazole alkaloids isolated show anti-microbial, anti-viral (Tubingensin A) and cytotoxic properties (Tubingensin B: a cytotoxic Carbazole alkaloid) against consumption of the sclerotia by insects (Govindasamy et al., 2003). Benzo- and pyrido-annulated carbazoles are pharmacologically interesting since such compounds have potential for the development of compounds with anti-tumor activity. From the above findings it is concluded that the title compound can act as an important synthon to derive such active carbazoles.

Gunaseelan et al. (2007a,b) have reported crystal structures of substituted carbazole derivatives, wherein the carbazole units are not planar. The molecular structure of the title compound, with atomic numbering scheme, is shown in Fig. 1. The carbazole unit is not planar. The dihedral angle between the benzene ring and the fused pyrrole ring is 2.5 (1)°. The cyclohexene ring is in envelope form. There is an intramolecular C9—H9A···O1 hydrogen bond.

Related literature top

Several authors (Chandrakantha et al., 1992; Rodriguez et al., 1985; Ebenezer Martin & Rajendra Prasad, 2006; Balamurali & Rajendra Prasad, 2001; Courseille et al., 1974; Govindasamy et al., 2003; Gunaseelan et al., 2007a,b) have reported crystal structures of substituted carbazole derivatives, wherein the carbazole units are not planar.

Experimental top

The mixture of 2,3,4,9-tetrahydro-1H-carbazol-1-one (185 mg, 0.001 mol), methyl iodide (1 ml) and ignited potassium carbonate (276 mg, 0.002 mol) in dry acetone (20 ml) was refluxed on a steam bath for 3 h. The reaction was monitored by TLC. After completion of the reaction, the solvent was removed by distillation and the mixture was poured into crushed ice. The solid obtained was filtered, washed with water and dried. It was purified by column chromatography over silica gel (60–120 mesh) using petroleum ether/ethyl acetate (98:2) as eluant to get the pure title compound (106 mg, 54%). It was recrystallized from petroleum ether/ethylacetate (90:10).

Refinement top

Owing to the absence of any anomalous scatterers in the molecule, the Friedel pairs were merged. The absolute structure in the present model have been chosen arbitrarily. H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.94–0.98 Å and Uiso(H) = 1.2–1.5 times Ueq(C). The methyl group was treated as an idealized disordered methyl group over two positions; coordinates riding with C—H = 0.97 Å and Uiso(H) = 1.5times Ueq(C9).

Structure description top

Indole and its various substituted products have long been known for their interesting chemical and biological activities (Chandrakantha et al., 1992). The indole ring system is present in a number of natural products, many of which are found to possess pharmacological properties like anti-microbial, anti-inflammatory and anti-implantation activities (Rodriguez et al., 1985; Ebenezer Martin & Rajendra Prasad, 2006; Balamurali & Rajendra Prasad, 2001). Carbazoles formed by the fusion of indole ring with aromatic six-membered ring, are also widely used in many areas in biological sciences. The structures of these derivatives are analogous to that of ellipticine, a plant alkaloid having pronounced anti-tumour activity and are found to have DNA intercalating properties (Courseille et al., 1974). Synthetic approaches to substituted carbazoles are of special interest and contemporary importance since the growing variety of carbazole alkaloids isolated show anti-microbial, anti-viral (Tubingensin A) and cytotoxic properties (Tubingensin B: a cytotoxic Carbazole alkaloid) against consumption of the sclerotia by insects (Govindasamy et al., 2003). Benzo- and pyrido-annulated carbazoles are pharmacologically interesting since such compounds have potential for the development of compounds with anti-tumor activity. From the above findings it is concluded that the title compound can act as an important synthon to derive such active carbazoles.

Gunaseelan et al. (2007a,b) have reported crystal structures of substituted carbazole derivatives, wherein the carbazole units are not planar. The molecular structure of the title compound, with atomic numbering scheme, is shown in Fig. 1. The carbazole unit is not planar. The dihedral angle between the benzene ring and the fused pyrrole ring is 2.5 (1)°. The cyclohexene ring is in envelope form. There is an intramolecular C9—H9A···O1 hydrogen bond.

Several authors (Chandrakantha et al., 1992; Rodriguez et al., 1985; Ebenezer Martin & Rajendra Prasad, 2006; Balamurali & Rajendra Prasad, 2001; Courseille et al., 1974; Govindasamy et al., 2003; Gunaseelan et al., 2007a,b) have reported crystal structures of substituted carbazole derivatives, wherein the carbazole units are not planar.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2007); 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 the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level. Only one component of the disordered methyl group was shown.
9-Methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one top
Crystal data top
C13H13NODx = 1.312 Mg m3
Mr = 199.24Melting point: 453(1) K
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 2548 reflections
a = 7.4974 (5) Åθ = 4.7–30.4°
b = 14.9690 (11) ŵ = 0.08 mm1
c = 8.9885 (10) ÅT = 203 K
V = 1008.77 (15) Å3Block, light-brown
Z = 40.39 × 0.37 × 0.28 mm
F(000) = 424
Data collection top
Oxford Diffraction Gemini
diffractometer
1464 independent reflections
Radiation source: fine-focus sealed tube1056 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
Detector resolution: 10.5081 pixels mm-1θmax = 30.5°, θmin = 5.3°
φ and ω scansh = 010
Absorption correction: multi-scan
(CrysAlis CCD or RED?; Oxford Diffraction, 2007)
k = 019
Tmin = 0.798, Tmax = 1.000l = 012
4884 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.106 w = 1/[σ2(Fo2) + (0.0626P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
1464 reflectionsΔρmax = 0.21 e Å3
136 parametersΔρmin = 0.30 e Å3
1 restraintAbsolute structure: see Refinement section in supplementary materials
Primary atom site location: structure-invariant direct methods
Crystal data top
C13H13NOV = 1008.77 (15) Å3
Mr = 199.24Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 7.4974 (5) ŵ = 0.08 mm1
b = 14.9690 (11) ÅT = 203 K
c = 8.9885 (10) Å0.39 × 0.37 × 0.28 mm
Data collection top
Oxford Diffraction Gemini
diffractometer
1464 independent reflections
Absorption correction: multi-scan
(CrysAlis CCD or RED?; Oxford Diffraction, 2007)
1056 reflections with I > 2σ(I)
Tmin = 0.798, Tmax = 1.000Rint = 0.052
4884 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0441 restraint
wR(F2) = 0.106H-atom parameters constrained
S = 1.02Δρmax = 0.21 e Å3
1464 reflectionsΔρmin = 0.30 e Å3
136 parametersAbsolute structure: see Refinement section in supplementary materials
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)
N90.2382 (2)0.25379 (10)0.0201 (2)0.0289 (4)
C4B0.2697 (2)0.39912 (14)0.0453 (3)0.0260 (5)
C4A0.1978 (3)0.39569 (13)0.1011 (3)0.0250 (5)
C9A0.1816 (3)0.30606 (12)0.1380 (3)0.0259 (5)
C50.3245 (3)0.46894 (13)0.1400 (3)0.0308 (6)
H50.31150.52890.11090.037*
C8A0.2933 (3)0.30931 (14)0.0925 (3)0.0283 (5)
O10.1064 (2)0.19597 (10)0.3163 (2)0.0496 (5)
C10.1188 (3)0.27520 (13)0.2818 (3)0.0310 (5)
C40.1455 (3)0.46920 (13)0.2044 (3)0.0300 (6)
H4A0.02220.48740.18460.036*
H4B0.22310.52110.18880.036*
C80.3655 (3)0.28846 (14)0.2314 (3)0.0358 (6)
H80.37800.22880.26250.043*
C70.4178 (3)0.35812 (15)0.3211 (3)0.0389 (6)
H70.46810.34570.41470.047*
C60.3975 (3)0.44756 (15)0.2758 (3)0.0370 (6)
H60.43460.49370.33970.044*
C90.2415 (3)0.15656 (12)0.0102 (4)0.0390 (6)
H9A0.19770.13120.10260.058*0.50
H9B0.36280.13660.00700.058*0.50
H9C0.16620.13730.07140.058*0.50
H9D0.28670.13880.08650.058*0.50
H9E0.12160.13340.02310.058*0.50
H9F0.31830.13270.08750.058*0.50
C20.0641 (3)0.34836 (14)0.3883 (3)0.0376 (6)
H2A0.08560.32790.49030.045*
H2B0.06430.35890.37770.045*
C30.1626 (3)0.43645 (15)0.3643 (3)0.0384 (6)
H3A0.11390.48170.43180.046*
H3B0.28900.42840.38850.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0612 (10)0.0345 (8)0.0532 (13)0.0010 (7)0.0077 (11)0.0149 (8)
N90.0321 (8)0.0220 (7)0.0327 (9)0.0002 (7)0.0026 (8)0.0005 (9)
C10.0236 (9)0.0336 (11)0.0358 (15)0.0005 (8)0.0037 (10)0.0056 (9)
C20.0394 (11)0.0390 (11)0.0345 (14)0.0025 (9)0.0046 (11)0.0026 (10)
C30.0478 (12)0.0348 (12)0.0327 (15)0.0042 (10)0.0016 (12)0.0029 (10)
C40.0314 (10)0.0261 (10)0.0326 (16)0.0001 (7)0.0009 (11)0.0024 (9)
C4A0.0230 (9)0.0243 (9)0.0277 (13)0.0002 (8)0.0048 (10)0.0011 (9)
C4B0.0223 (8)0.0253 (10)0.0304 (12)0.0017 (7)0.0043 (10)0.0019 (9)
C50.0274 (9)0.0273 (10)0.0377 (16)0.0027 (8)0.0016 (11)0.0077 (10)
C60.0334 (10)0.0410 (11)0.0366 (16)0.0035 (9)0.0007 (12)0.0140 (11)
C70.0355 (12)0.0545 (14)0.0267 (13)0.0091 (9)0.0027 (11)0.0002 (11)
C80.0345 (10)0.0374 (12)0.0355 (16)0.0041 (9)0.0041 (11)0.0101 (11)
C8A0.0243 (9)0.0283 (10)0.0321 (15)0.0018 (8)0.0059 (10)0.0016 (9)
C90.0431 (11)0.0213 (9)0.0526 (16)0.0018 (9)0.0100 (12)0.0033 (11)
C9A0.0219 (9)0.0274 (10)0.0285 (14)0.0003 (8)0.0045 (9)0.0013 (9)
Geometric parameters (Å, º) top
O1—C11.229 (3)C2—H2A0.9800
N9—C8A1.373 (3)C2—H2B0.9800
N9—C91.458 (2)C3—H3A0.9800
N9—C9A1.384 (3)C3—H3B0.9800
C1—C21.511 (3)C4—H4A0.9800
C1—C9A1.451 (4)C4—H4B0.9800
C2—C31.527 (3)C5—H50.9400
C3—C41.524 (4)C6—H60.9400
C4—C4A1.492 (3)C7—H70.9400
C4A—C4B1.423 (4)C8—H80.9400
C4A—C9A1.387 (3)C9—H9A0.9700
C4B—C51.409 (3)C9—H9B0.9700
C4B—C8A1.421 (3)C9—H9C0.9700
C5—C61.376 (4)C9—H9D0.9700
C6—C71.408 (3)C9—H9E0.9700
C7—C81.375 (3)C9—H9F0.9700
C8—C8A1.396 (4)
O1···N92.969 (3)H3A···H9Dv2.4700
O1···C92.991 (4)H3B···C7x2.9800
O1···H9A2.2600H3B···C9A3.0100
O1···H9E2.8000H3B···H7x2.5400
O1···H9F2.7700H4A···H3Axii2.5300
O1···H5i2.6600H4A···H9Fiv2.5200
O1···H2Bii2.6600H4B···C6xiii2.9000
O1···H7iii2.7000H4B···H6xiii2.5900
N9···O12.969 (3)H5···H2Bxii2.5000
C8A···C9ii3.522 (3)H5···O1vi2.6600
C9···O12.991 (4)H6···H4Bvii2.5900
C9···C9Aii3.538 (3)H6···C9vi3.0800
C9···C8Aiv3.522 (3)H6···H9Avi2.3400
C9A···C9iv3.538 (3)H6···H9Evi2.4700
C1···H9A2.7600H7···H3Bviii2.5400
C3···H9Dv3.0900H7···O1xiv2.7000
C4···H9Fiv3.0700H8···C92.8700
C4A···H9Biv2.7400H8···H9D2.1900
C4A···H9Fiv2.8800H9A···O12.2600
C4B···H9Eii2.7500H9A···C12.7600
C4B···H9Cii3.0300H9A···C6i3.0400
C5···H9Cii3.0800H9A···H6i2.3400
C5···H9Eii3.0800H9B···C83.0400
C6···H9Avi3.0400H9B···H3Aix2.3900
C6···H4Bvii2.9000H9B···C4Aii2.7400
C6···H9Cii3.0100H9B···C9Aii2.8500
C7···H3Bviii2.9800H9C···C83.0700
C7···H9Cii2.9200H9C···C4Biv3.0300
C7···H2Aviii3.0500H9C···C5iv3.0800
C8···H9Cii2.9000H9C···C6iv3.0100
C8···H9C3.0700H9C···C7iv2.9200
C8···H9D2.6600H9C···C8iv2.9000
C8···H9B3.0400H9C···C8Aiv2.9100
C8A···H9Eii2.8100H9D···C82.6600
C8A···H9Cii2.9100H9D···H82.1900
C9···H6i3.0800H9D···C3ix3.0900
C9···H3Aix2.9200H9D···H3Aix2.4700
C9···H82.8700H9E···O12.8000
C9A···H3B3.0100H9E···H6i2.4700
C9A···H9Biv2.8500H9E···C4Biv2.7500
C9A···H9Fiv2.9100H9E···C5iv3.0800
H2A···C7x3.0500H9E···C8Aiv2.8100
H2B···H5xi2.5000H9F···O12.7700
H2B···O1iv2.6600H9F···C4ii3.0700
H3A···H4Axi2.5300H9F···C4Aii2.8800
H3A···C9v2.9200H9F···C9Aii2.9100
H3A···H9Bv2.3900H9F···H4Aii2.5200
C8A—N9—C9123.7 (2)C3—C4—H4A110.00
C8A—N9—C9A108.33 (16)C3—C4—H4B110.00
C9—N9—C9A128.0 (2)C4A—C4—H4A110.00
O1—C1—C2121.3 (2)C4A—C4—H4B110.00
O1—C1—C9A123.8 (2)H4A—C4—H4B108.00
C2—C1—C9A114.93 (18)C4B—C5—H5121.00
C1—C2—C3113.9 (2)C6—C5—H5121.00
C2—C3—C4111.7 (2)C5—C6—H6119.00
C3—C4—C4A109.12 (18)C7—C6—H6119.00
C4—C4A—C4B130.42 (19)C6—C7—H7119.00
C4—C4A—C9A122.8 (2)C8—C7—H7119.00
C4B—C4A—C9A106.8 (2)C7—C8—H8121.00
C4A—C4B—C5134.1 (2)C8A—C8—H8121.00
C4A—C4B—C8A106.8 (2)N9—C9—H9A109.00
C5—C4B—C8A119.0 (2)N9—C9—H9B109.00
C4B—C5—C6118.7 (2)N9—C9—H9C109.00
C5—C6—C7121.4 (2)N9—C9—H9D109.00
C6—C7—C8121.4 (2)N9—C9—H9E109.00
C7—C8—C8A117.7 (2)N9—C9—H9F109.00
N9—C8A—C4B108.4 (2)H9A—C9—H9B109.00
N9—C8A—C8129.8 (2)H9A—C9—H9C109.00
C4B—C8A—C8121.8 (2)H9A—C9—H9D141.00
N9—C9A—C1126.99 (17)H9A—C9—H9E56.00
N9—C9A—C4A109.7 (2)H9A—C9—H9F56.00
C1—C9A—C4A123.3 (2)H9B—C9—H9C109.00
C1—C2—H2A109.00H9B—C9—H9D56.00
C1—C2—H2B109.00H9B—C9—H9E141.00
C3—C2—H2A109.00H9B—C9—H9F56.00
C3—C2—H2B109.00H9C—C9—H9D56.00
H2A—C2—H2B108.00H9C—C9—H9E56.00
C2—C3—H3A109.00H9C—C9—H9F141.00
C2—C3—H3B109.00H9D—C9—H9E109.00
C4—C3—H3A109.00H9D—C9—H9F109.00
C4—C3—H3B109.00H9E—C9—H9F109.00
H3A—C3—H3B108.00
C9—N9—C8A—C4B179.30 (19)C4—C4A—C4B—C8A179.6 (2)
C9—N9—C8A—C82.2 (4)C9A—C4A—C4B—C5176.2 (2)
C9A—N9—C8A—C4B0.4 (2)C9A—C4A—C4B—C8A0.5 (2)
C9A—N9—C8A—C8178.1 (2)C4—C4A—C9A—N9179.3 (2)
C8A—N9—C9A—C1177.6 (2)C4—C4A—C9A—C12.4 (4)
C8A—N9—C9A—C4A0.7 (3)C4B—C4A—C9A—N90.7 (3)
C9—N9—C9A—C12.7 (4)C4B—C4A—C9A—C1177.6 (2)
C9—N9—C9A—C4A179.0 (2)C4A—C4B—C5—C6176.9 (2)
O1—C1—C2—C3152.8 (2)C8A—C4B—C5—C60.6 (3)
C9A—C1—C2—C328.5 (3)C4A—C4B—C8A—N90.0 (2)
O1—C1—C9A—N90.9 (4)C4A—C4B—C8A—C8178.7 (2)
O1—C1—C9A—C4A178.9 (2)C5—C4B—C8A—N9177.21 (18)
C2—C1—C9A—N9179.5 (2)C5—C4B—C8A—C81.5 (3)
C2—C1—C9A—C4A2.4 (3)C4B—C5—C6—C70.1 (3)
C1—C2—C3—C454.6 (3)C5—C6—C7—C80.0 (4)
C2—C3—C4—C4A51.8 (2)C6—C7—C8—C8A0.8 (3)
C3—C4—C4A—C4B152.8 (2)C7—C8—C8A—N9176.8 (2)
C3—C4—C4A—C9A27.2 (3)C7—C8—C8A—C4B1.5 (3)
C4—C4A—C4B—C53.8 (4)
Symmetry codes: (i) x+1/2, y1/2, z+1/2; (ii) x+1/2, y+1/2, z; (iii) x1/2, y+1/2, z+1; (iv) x1/2, y+1/2, z; (v) x+1/2, y+1/2, z+1/2; (vi) x+1/2, y+1/2, z1/2; (vii) x+1, y+1, z1/2; (viii) x, y, z1; (ix) x+1/2, y1/2, z1/2; (x) x, y, z+1; (xi) x, y+1, z+1/2; (xii) x, y+1, z1/2; (xiii) x+1, y+1, z+1/2; (xiv) x+1/2, y+1/2, z1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···O10.972.262.991 (4)131

Experimental details

Crystal data
Chemical formulaC13H13NO
Mr199.24
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)203
a, b, c (Å)7.4974 (5), 14.9690 (11), 8.9885 (10)
V3)1008.77 (15)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.39 × 0.37 × 0.28
Data collection
DiffractometerOxford Diffraction Gemini
Absorption correctionMulti-scan
(CrysAlis CCD or RED?; Oxford Diffraction, 2007)
Tmin, Tmax0.798, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
4884, 1464, 1056
Rint0.052
(sin θ/λ)max1)0.714
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.106, 1.02
No. of reflections1464
No. of parameters136
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.30
Absolute structureSee Refinement section in supplementary materials

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis CCD, CrysAlis RED (Oxford Diffraction, 2007), 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
C9—H9A···O10.97002.26002.991 (4)131.00
 

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