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In the title compound, C24H19NO3, the six-membered ring with the methyl substituents is in an envelope conformation. The crystal structure is stabilized by C—H...O, C—H...π and π–π inter­actions; the latter involve centroid–centroid distances of 3.680 (1) and 3.802 (1) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027213/wn2149sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027213/wn2149Isup2.hkl
Contains datablock I

CCDC reference: 654907

Key indicators

  • Single-crystal X-ray study
  • T = 105 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.052
  • wR factor = 0.131
  • Data-to-parameter ratio = 20.5

checkCIF/PLATON results

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Alert level C PLAT333_ALERT_2_C Large Average Benzene C-C Dist. C1 -C10 1.45 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Benzo[b]carbazole-6,11-diones, as bisannulated indoloquinones, are important synthetic targets (Cone et al., 1989). However, a majority of the present synthetic methods for them are based on rather long reaction sequences. We have recently reported a direct one-pot synthesis of benzo[b]carbazole-6,11-diones (Hu et al., 2006). The title compound, a derivative of benzo[b]carbazole-6,11-dione, was isolated from the C,N-dialkylation of the cyclic β-enaminone of 5,5-dimethyl-3-(phenylamino)cyclohex-2-en-1-one by 2,3-dichloro-1,4-naphthalenedione.

Bond lengths and angles in the title compound have normal values (Allen et al., 1987), comparable to a related structure (Fun et al., 2007). The C11—C16 ring adopts an envelope conformation, with C14 deviating from the plane of the other five atoms by 0.621 (1) Å. The puckering parameters are Q = 0.453 (2) Å, θ = 50.1 (3)° and φ = 170.7 (3)° (Cremer & Pople, 1975). The C17—C22 ring is almost perpendicular to the pyrrole ring; the dihedral angle between the N1/C1/C10/C11/C16 and C17—C22 rings is 77.92 (8)°.

The crystal structure is stabilized by intermolecular C—H···O interactions (Fig. 2 and Table 1) and also C—H···π interactions involving the C3—C8 ring (centroid Cg1) (Table 1). π-π interactions provide additional stability; the centroid-centroid distance between the N1/C1/C10/C11/C16 rings at (x, y, z) and (1 - x, 1 - y, -z) is 3.802 (1) Å, and that between the N1/C1/C10/C11/C16 rings at (x, y, z) and the C1—C3/C8—C10 ring at (1 - x, 1 - y, -z) is 3.680 (1) Å.

Related literature top

For bond-length data, see: Allen et al. (1987). For related literature, see: Cone et al. (1989); Cremer & Pople (1975); Hu et al. (2006); Fun et al. (2007).

Experimental top

A mixture of 2,3-dichloro-1,4-naphthalenedione (1.1 mmol), 5,5-dimethyl-3-(phenylamino)cyclohex-2-en-1-one (1 mmol) and Na2CO3 (2.5 mmol) in DMF (15 ml) was heated under reflux for 6 h with magnetic stirring and TLC monitoring of the reaction. The solvent was removed under reduced pressure, and the residual solid was separated by flash chromatography on a silica gel column, with petroleum ether-ethyl acetate as eluents, to give the title compound. Single crystals were obtained by slow evaporation of a petroleum ether-ethyl acetate (3:1) solvent system (yield 75%); m.p 532–533 K.

Refinement top

H atoms were positioned geometrically and treated as riding, with C—H = 0.93–0.97 Å and the Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Structure description top

Benzo[b]carbazole-6,11-diones, as bisannulated indoloquinones, are important synthetic targets (Cone et al., 1989). However, a majority of the present synthetic methods for them are based on rather long reaction sequences. We have recently reported a direct one-pot synthesis of benzo[b]carbazole-6,11-diones (Hu et al., 2006). The title compound, a derivative of benzo[b]carbazole-6,11-dione, was isolated from the C,N-dialkylation of the cyclic β-enaminone of 5,5-dimethyl-3-(phenylamino)cyclohex-2-en-1-one by 2,3-dichloro-1,4-naphthalenedione.

Bond lengths and angles in the title compound have normal values (Allen et al., 1987), comparable to a related structure (Fun et al., 2007). The C11—C16 ring adopts an envelope conformation, with C14 deviating from the plane of the other five atoms by 0.621 (1) Å. The puckering parameters are Q = 0.453 (2) Å, θ = 50.1 (3)° and φ = 170.7 (3)° (Cremer & Pople, 1975). The C17—C22 ring is almost perpendicular to the pyrrole ring; the dihedral angle between the N1/C1/C10/C11/C16 and C17—C22 rings is 77.92 (8)°.

The crystal structure is stabilized by intermolecular C—H···O interactions (Fig. 2 and Table 1) and also C—H···π interactions involving the C3—C8 ring (centroid Cg1) (Table 1). π-π interactions provide additional stability; the centroid-centroid distance between the N1/C1/C10/C11/C16 rings at (x, y, z) and (1 - x, 1 - y, -z) is 3.802 (1) Å, and that between the N1/C1/C10/C11/C16 rings at (x, y, z) and the C1—C3/C8—C10 ring at (1 - x, 1 - y, -z) is 3.680 (1) Å.

For bond-length data, see: Allen et al. (1987). For related literature, see: Cone et al. (1989); Cremer & Pople (1975); Hu et al. (2006); Fun et al. (2007).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed down the a axis. H atoms not involved in intermolecular hydrogen bonding (dashed lines) have been omitted.
3,3-Dimethyl-5-phenyl-3,4-dihydro-1H-benzo[b]carbazole-1,6,11(2H,5H)-trione top
Crystal data top
C24H19NO3F(000) = 776
Mr = 369.40Dx = 1.368 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4781 reflections
a = 10.0097 (4) Åθ = 2.2–30.0°
b = 10.3559 (3) ŵ = 0.09 mm1
c = 18.8030 (6) ÅT = 105 K
β = 113.032 (2)°Block, yellow
V = 1793.74 (11) Å30.44 × 0.44 × 0.21 mm
Z = 4
Data collection top
Bruker SMART APEX II CCD
diffractometer
5227 independent reflections
Radiation source: fine-focus sealed tube3937 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
Detector resolution: 8.33 pixels mm-1θmax = 30.0°, θmin = 2.2°
ω scansh = 1410
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1414
Tmin = 0.923, Tmax = 0.981l = 2326
20016 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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.058P)2 + 0.6108P]
where P = (Fo2 + 2Fc2)/3
5227 reflections(Δ/σ)max < 0.001
255 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
C24H19NO3V = 1793.74 (11) Å3
Mr = 369.40Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.0097 (4) ŵ = 0.09 mm1
b = 10.3559 (3) ÅT = 105 K
c = 18.8030 (6) Å0.44 × 0.44 × 0.21 mm
β = 113.032 (2)°
Data collection top
Bruker SMART APEX II CCD
diffractometer
5227 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
3937 reflections with I > 2σ(I)
Tmin = 0.923, Tmax = 0.981Rint = 0.045
20016 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0520 restraints
wR(F2) = 0.131H-atom parameters constrained
S = 1.04Δρmax = 0.40 e Å3
5227 reflectionsΔρmin = 0.25 e Å3
255 parameters
Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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*/Ueq
O10.88629 (12)0.46854 (10)0.06989 (7)0.0276 (3)
O20.48911 (12)0.84168 (10)0.04046 (7)0.0294 (3)
O30.29406 (13)0.73100 (11)0.10322 (8)0.0364 (3)
N10.65186 (13)0.43131 (11)0.12615 (7)0.0167 (2)
C10.67700 (15)0.53791 (13)0.08874 (8)0.0165 (3)
C20.79625 (15)0.55284 (13)0.06292 (8)0.0188 (3)
C30.80114 (15)0.68082 (13)0.02733 (8)0.0177 (3)
C40.91277 (16)0.70517 (14)0.00263 (8)0.0216 (3)
H4A0.98240.64220.00820.026*
C50.92026 (17)0.82360 (15)0.03028 (9)0.0257 (3)
H5A0.99500.83980.04670.031*
C60.81637 (17)0.91787 (15)0.03875 (9)0.0256 (3)
H6A0.82150.99680.06120.031*
C70.70500 (17)0.89488 (14)0.01394 (8)0.0213 (3)
H7A0.63610.95850.01940.026*
C80.69637 (15)0.77623 (13)0.01928 (8)0.0179 (3)
C90.57515 (15)0.75543 (13)0.04574 (8)0.0181 (3)
C100.56930 (15)0.62804 (13)0.07879 (8)0.0164 (3)
C110.47292 (15)0.57373 (13)0.11076 (8)0.0172 (3)
C120.34326 (16)0.62263 (14)0.12104 (9)0.0211 (3)
C130.27163 (16)0.52641 (14)0.15548 (9)0.0221 (3)
H13A0.20270.47600.11370.027*
H13B0.21700.57390.17960.027*
C140.37449 (16)0.43246 (13)0.21565 (8)0.0197 (3)
C150.46719 (15)0.36058 (13)0.17948 (8)0.0185 (3)
H15A0.54540.31510.21950.022*
H15B0.40770.29740.14260.022*
C160.52900 (15)0.45310 (13)0.13976 (8)0.0168 (3)
C170.75680 (15)0.33105 (13)0.16409 (8)0.0179 (3)
C180.77517 (17)0.22589 (14)0.12389 (9)0.0233 (3)
H18A0.72060.21730.07120.028*
C190.87714 (18)0.13282 (15)0.16385 (10)0.0285 (4)
H19A0.88960.06030.13790.034*
C200.95985 (18)0.14733 (16)0.24163 (10)0.0313 (4)
H20A1.02890.08530.26770.038*
C210.94077 (18)0.25331 (16)0.28107 (10)0.0299 (4)
H21A0.99700.26280.33350.036*
C220.83737 (16)0.34590 (14)0.24236 (9)0.0227 (3)
H22A0.82260.41680.26870.027*
C230.47307 (18)0.50570 (15)0.28774 (9)0.0262 (3)
H23A0.53200.44530.32580.039*
H23D0.41460.55420.30830.039*
H23B0.53440.56350.27430.039*
C240.28358 (18)0.33466 (15)0.23837 (10)0.0267 (3)
H24D0.34660.27300.27380.040*
H24A0.21890.29070.19300.040*
H24B0.22810.37890.26250.040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0270 (6)0.0222 (5)0.0408 (6)0.0090 (4)0.0211 (5)0.0088 (5)
O20.0330 (6)0.0195 (5)0.0423 (7)0.0108 (5)0.0219 (5)0.0095 (5)
O30.0316 (7)0.0221 (5)0.0662 (9)0.0117 (5)0.0309 (6)0.0124 (6)
N10.0182 (6)0.0132 (5)0.0197 (6)0.0024 (4)0.0085 (5)0.0021 (4)
C10.0164 (7)0.0144 (6)0.0181 (6)0.0015 (5)0.0061 (5)0.0005 (5)
C20.0182 (7)0.0177 (6)0.0200 (7)0.0016 (5)0.0070 (6)0.0002 (5)
C30.0179 (7)0.0172 (6)0.0168 (6)0.0006 (5)0.0055 (5)0.0006 (5)
C40.0199 (7)0.0224 (7)0.0233 (7)0.0000 (6)0.0094 (6)0.0001 (6)
C50.0256 (8)0.0258 (7)0.0287 (8)0.0055 (6)0.0139 (7)0.0001 (6)
C60.0292 (8)0.0196 (7)0.0285 (8)0.0049 (6)0.0119 (7)0.0028 (6)
C70.0254 (8)0.0157 (6)0.0224 (7)0.0001 (5)0.0089 (6)0.0001 (5)
C80.0201 (7)0.0150 (6)0.0169 (6)0.0004 (5)0.0054 (5)0.0009 (5)
C90.0198 (7)0.0158 (6)0.0184 (6)0.0020 (5)0.0070 (5)0.0002 (5)
C100.0174 (7)0.0146 (6)0.0171 (6)0.0015 (5)0.0065 (5)0.0005 (5)
C110.0172 (7)0.0146 (6)0.0194 (6)0.0013 (5)0.0069 (5)0.0009 (5)
C120.0199 (7)0.0182 (6)0.0268 (7)0.0024 (5)0.0110 (6)0.0001 (6)
C130.0200 (7)0.0201 (7)0.0297 (8)0.0014 (5)0.0135 (6)0.0018 (6)
C140.0211 (7)0.0169 (6)0.0248 (7)0.0002 (5)0.0130 (6)0.0015 (5)
C150.0180 (7)0.0158 (6)0.0236 (7)0.0006 (5)0.0102 (6)0.0000 (5)
C160.0165 (7)0.0152 (6)0.0192 (6)0.0006 (5)0.0075 (5)0.0013 (5)
C170.0159 (7)0.0143 (6)0.0247 (7)0.0022 (5)0.0093 (6)0.0050 (5)
C180.0231 (8)0.0204 (7)0.0277 (8)0.0038 (6)0.0112 (6)0.0011 (6)
C190.0318 (9)0.0191 (7)0.0425 (9)0.0096 (6)0.0232 (8)0.0074 (7)
C200.0254 (8)0.0310 (8)0.0430 (10)0.0135 (7)0.0195 (8)0.0204 (7)
C210.0227 (8)0.0362 (9)0.0279 (8)0.0055 (7)0.0067 (7)0.0120 (7)
C220.0205 (7)0.0225 (7)0.0254 (7)0.0009 (6)0.0093 (6)0.0030 (6)
C230.0347 (9)0.0212 (7)0.0248 (7)0.0019 (6)0.0139 (7)0.0028 (6)
C240.0306 (8)0.0218 (7)0.0340 (8)0.0012 (6)0.0192 (7)0.0012 (6)
Geometric parameters (Å, º) top
O1—C21.2244 (17)C13—H13A0.9700
O2—C91.2176 (17)C13—H13B0.9700
O3—C121.2187 (17)C14—C231.530 (2)
N1—C161.3693 (18)C14—C241.530 (2)
N1—C11.3839 (17)C14—C151.5398 (19)
N1—C171.4505 (17)C15—C161.4901 (19)
C1—C101.3822 (18)C15—H15A0.9700
C1—C21.4622 (19)C15—H15B0.9700
C2—C31.4942 (19)C17—C181.378 (2)
C3—C41.391 (2)C17—C221.382 (2)
C3—C81.4052 (19)C18—C191.391 (2)
C4—C51.389 (2)C18—H18A0.9300
C4—H4A0.9300C19—C201.378 (2)
C5—C61.389 (2)C19—H19A0.9300
C5—H5A0.9300C20—C211.379 (2)
C6—C71.387 (2)C20—H20A0.9300
C6—H6A0.9300C21—C221.390 (2)
C7—C81.3963 (19)C21—H21A0.9300
C7—H7A0.9300C22—H22A0.9300
C8—C91.496 (2)C23—H23A0.9600
C9—C101.4691 (18)C23—H23D0.9600
C10—C111.4362 (19)C23—H23B0.9600
C11—C161.3905 (18)C24—H24D0.9600
C11—C121.4745 (19)C24—H24A0.9600
C12—C131.513 (2)C24—H24B0.9600
C13—C141.541 (2)
C16—N1—C1108.59 (11)C23—C14—C24109.19 (12)
C16—N1—C17123.82 (11)C23—C14—C15109.86 (12)
C1—N1—C17125.47 (11)C24—C14—C15109.29 (12)
C10—C1—N1108.68 (12)C23—C14—C13110.58 (12)
C10—C1—C2125.34 (12)C24—C14—C13108.87 (12)
N1—C1—C2125.98 (12)C15—C14—C13109.02 (12)
O1—C2—C1123.46 (13)C16—C15—C14110.52 (11)
O1—C2—C3121.92 (13)C16—C15—H15A109.5
C1—C2—C3114.62 (12)C14—C15—H15A109.5
C4—C3—C8119.99 (13)C16—C15—H15B109.5
C4—C3—C2118.80 (13)C14—C15—H15B109.5
C8—C3—C2121.21 (12)H15A—C15—H15B108.1
C5—C4—C3119.96 (14)N1—C16—C11109.22 (12)
C5—C4—H4A120.0N1—C16—C15124.55 (12)
C3—C4—H4A120.0C11—C16—C15126.24 (12)
C4—C5—C6120.21 (14)C18—C17—C22121.62 (13)
C4—C5—H5A119.9C18—C17—N1121.47 (13)
C6—C5—H5A119.9C22—C17—N1116.91 (12)
C7—C6—C5120.32 (14)C17—C18—C19118.57 (14)
C7—C6—H6A119.8C17—C18—H18A120.7
C5—C6—H6A119.8C19—C18—H18A120.7
C6—C7—C8120.00 (14)C20—C19—C18120.46 (15)
C6—C7—H7A120.0C20—C19—H19A119.8
C8—C7—H7A120.0C18—C19—H19A119.8
C7—C8—C3119.52 (13)C19—C20—C21120.35 (14)
C7—C8—C9118.40 (13)C19—C20—H20A119.8
C3—C8—C9122.08 (12)C21—C20—H20A119.8
O2—C9—C10123.31 (13)C20—C21—C22119.93 (15)
O2—C9—C8120.47 (13)C20—C21—H21A120.0
C10—C9—C8116.21 (12)C22—C21—H21A120.0
C1—C10—C11107.15 (12)C17—C22—C21119.05 (14)
C1—C10—C9120.38 (12)C17—C22—H22A120.5
C11—C10—C9132.31 (12)C21—C22—H22A120.5
C16—C11—C10106.36 (12)C14—C23—H23A109.5
C16—C11—C12119.88 (13)C14—C23—H23D109.5
C10—C11—C12133.65 (12)H23A—C23—H23D109.5
O3—C12—C11124.19 (14)C14—C23—H23B109.5
O3—C12—C13121.06 (13)H23A—C23—H23B109.5
C11—C12—C13114.75 (12)H23D—C23—H23B109.5
C12—C13—C14115.95 (12)C14—C24—H24D109.5
C12—C13—H13A108.3C14—C24—H24A109.5
C14—C13—H13A108.3H24D—C24—H24A109.5
C12—C13—H13B108.3C14—C24—H24B109.5
C14—C13—H13B108.3H24D—C24—H24B109.5
H13A—C13—H13B107.4H24A—C24—H24B109.5
C16—N1—C1—C100.16 (15)C1—C10—C11—C12176.89 (15)
C17—N1—C1—C10163.70 (12)C9—C10—C11—C121.6 (3)
C16—N1—C1—C2179.09 (13)C16—C11—C12—O3173.72 (15)
C17—N1—C1—C217.0 (2)C10—C11—C12—O31.9 (3)
C10—C1—C2—O1176.81 (14)C16—C11—C12—C136.89 (19)
N1—C1—C2—O12.3 (2)C10—C11—C12—C13177.52 (14)
C10—C1—C2—C33.6 (2)O3—C12—C13—C14146.12 (15)
N1—C1—C2—C3177.25 (12)C11—C12—C13—C1434.47 (18)
O1—C2—C3—C41.0 (2)C12—C13—C14—C2365.39 (16)
C1—C2—C3—C4178.52 (13)C12—C13—C14—C24174.65 (12)
O1—C2—C3—C8179.56 (14)C12—C13—C14—C1555.50 (16)
C1—C2—C3—C80.87 (19)C23—C14—C15—C1673.91 (15)
C8—C3—C4—C50.3 (2)C24—C14—C15—C16166.31 (12)
C2—C3—C4—C5179.67 (13)C13—C14—C15—C1647.42 (15)
C3—C4—C5—C60.1 (2)C1—N1—C16—C110.41 (15)
C4—C5—C6—C70.5 (2)C17—N1—C16—C11164.60 (12)
C5—C6—C7—C80.4 (2)C1—N1—C16—C15179.61 (13)
C6—C7—C8—C30.0 (2)C17—N1—C16—C1515.4 (2)
C6—C7—C8—C9179.64 (13)C10—C11—C16—N10.79 (15)
C4—C3—C8—C70.3 (2)C12—C11—C16—N1177.47 (12)
C2—C3—C8—C7179.69 (12)C10—C11—C16—C15179.23 (13)
C4—C3—C8—C9179.28 (13)C12—C11—C16—C152.6 (2)
C2—C3—C8—C90.1 (2)C14—C15—C16—N1155.83 (13)
C7—C8—C9—O22.2 (2)C14—C15—C16—C1124.20 (19)
C3—C8—C9—O2177.36 (14)C16—N1—C17—C18111.91 (16)
C7—C8—C9—C10178.78 (12)C1—N1—C17—C1886.59 (17)
C3—C8—C9—C101.62 (19)C16—N1—C17—C2268.08 (17)
N1—C1—C10—C110.64 (15)C1—N1—C17—C2293.42 (16)
C2—C1—C10—C11178.62 (13)C22—C17—C18—C190.3 (2)
N1—C1—C10—C9175.32 (12)N1—C17—C18—C19179.65 (13)
C2—C1—C10—C95.4 (2)C17—C18—C19—C201.3 (2)
O2—C9—C10—C1174.82 (14)C18—C19—C20—C211.1 (2)
C8—C9—C10—C14.13 (19)C19—C20—C21—C220.2 (2)
O2—C9—C10—C110.0 (2)C18—C17—C22—C210.9 (2)
C8—C9—C10—C11178.92 (14)N1—C17—C22—C21179.09 (13)
C1—C10—C11—C160.88 (15)C20—C21—C22—C171.2 (2)
C9—C10—C11—C16174.42 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4A···O1i0.932.593.360 (2)140
C7—H7A···O2ii0.932.373.272 (2)163
C18—H18A···O2iii0.932.403.262 (2)155
C15—H15B···Cg1iii0.972.823.742 (2)158
Symmetry codes: (i) x+2, y+1, z; (ii) x+1, y+2, z; (iii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC24H19NO3
Mr369.40
Crystal system, space groupMonoclinic, P21/c
Temperature (K)105
a, b, c (Å)10.0097 (4), 10.3559 (3), 18.8030 (6)
β (°) 113.032 (2)
V3)1793.74 (11)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.44 × 0.44 × 0.21
Data collection
DiffractometerBruker SMART APEX II CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.923, 0.981
No. of measured, independent and
observed [I > 2σ(I)] reflections
20016, 5227, 3937
Rint0.045
(sin θ/λ)max1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.131, 1.04
No. of reflections5227
No. of parameters255
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.40, 0.25

Computer programs: APEX2 (Bruker, 2005), APEX2, SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4A···O1i0.932.593.360 (2)140
C7—H7A···O2ii0.932.373.272 (2)163
C18—H18A···O2iii0.932.403.262 (2)155
C15—H15B···Cg1iii0.972.823.742 (2)158
Symmetry codes: (i) x+2, y+1, z; (ii) x+1, y+2, z; (iii) x+1, y+1, z.
 

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