Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027213/wn2149sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027213/wn2149Isup2.hkl |
CCDC reference: 654907
Key indicators
- Single-crystal X-ray study
- T = 105 K
- Mean (C-C) = 0.002 Å
- R factor = 0.052
- wR factor = 0.131
- Data-to-parameter ratio = 20.5
checkCIF/PLATON results
No syntax errors found
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
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.
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).
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).
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).
C24H19NO3 | F(000) = 776 |
Mr = 369.40 | Dx = 1.368 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4781 reflections |
a = 10.0097 (4) Å | θ = 2.2–30.0° |
b = 10.3559 (3) Å | µ = 0.09 mm−1 |
c = 18.8030 (6) Å | T = 105 K |
β = 113.032 (2)° | Block, yellow |
V = 1793.74 (11) Å3 | 0.44 × 0.44 × 0.21 mm |
Z = 4 |
Bruker SMART APEX II CCD diffractometer | 5227 independent reflections |
Radiation source: fine-focus sealed tube | 3937 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
Detector resolution: 8.33 pixels mm-1 | θmax = 30.0°, θmin = 2.2° |
ω scans | h = −14→10 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −14→14 |
Tmin = 0.923, Tmax = 0.981 | l = −23→26 |
20016 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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.131 | H-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 parameters | Δρmax = 0.40 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
C24H19NO3 | V = 1793.74 (11) Å3 |
Mr = 369.40 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.0097 (4) Å | µ = 0.09 mm−1 |
b = 10.3559 (3) Å | T = 105 K |
c = 18.8030 (6) Å | 0.44 × 0.44 × 0.21 mm |
β = 113.032 (2)° |
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 = 0.981 | Rint = 0.045 |
20016 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.131 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.40 e Å−3 |
5227 reflections | Δρmin = −0.25 e Å−3 |
255 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.88629 (12) | 0.46854 (10) | 0.06989 (7) | 0.0276 (3) | |
O2 | 0.48911 (12) | 0.84168 (10) | 0.04046 (7) | 0.0294 (3) | |
O3 | 0.29406 (13) | 0.73100 (11) | 0.10322 (8) | 0.0364 (3) | |
N1 | 0.65186 (13) | 0.43131 (11) | 0.12615 (7) | 0.0167 (2) | |
C1 | 0.67700 (15) | 0.53791 (13) | 0.08874 (8) | 0.0165 (3) | |
C2 | 0.79625 (15) | 0.55284 (13) | 0.06292 (8) | 0.0188 (3) | |
C3 | 0.80114 (15) | 0.68082 (13) | 0.02733 (8) | 0.0177 (3) | |
C4 | 0.91277 (16) | 0.70517 (14) | 0.00263 (8) | 0.0216 (3) | |
H4A | 0.9824 | 0.6422 | 0.0082 | 0.026* | |
C5 | 0.92026 (17) | 0.82360 (15) | −0.03028 (9) | 0.0257 (3) | |
H5A | 0.9950 | 0.8398 | −0.0467 | 0.031* | |
C6 | 0.81637 (17) | 0.91787 (15) | −0.03875 (9) | 0.0256 (3) | |
H6A | 0.8215 | 0.9968 | −0.0612 | 0.031* | |
C7 | 0.70500 (17) | 0.89488 (14) | −0.01394 (8) | 0.0213 (3) | |
H7A | 0.6361 | 0.9585 | −0.0194 | 0.026* | |
C8 | 0.69637 (15) | 0.77623 (13) | 0.01928 (8) | 0.0179 (3) | |
C9 | 0.57515 (15) | 0.75543 (13) | 0.04574 (8) | 0.0181 (3) | |
C10 | 0.56930 (15) | 0.62804 (13) | 0.07879 (8) | 0.0164 (3) | |
C11 | 0.47292 (15) | 0.57373 (13) | 0.11076 (8) | 0.0172 (3) | |
C12 | 0.34326 (16) | 0.62263 (14) | 0.12104 (9) | 0.0211 (3) | |
C13 | 0.27163 (16) | 0.52641 (14) | 0.15548 (9) | 0.0221 (3) | |
H13A | 0.2027 | 0.4760 | 0.1137 | 0.027* | |
H13B | 0.2170 | 0.5739 | 0.1796 | 0.027* | |
C14 | 0.37449 (16) | 0.43246 (13) | 0.21565 (8) | 0.0197 (3) | |
C15 | 0.46719 (15) | 0.36058 (13) | 0.17948 (8) | 0.0185 (3) | |
H15A | 0.5454 | 0.3151 | 0.2195 | 0.022* | |
H15B | 0.4077 | 0.2974 | 0.1426 | 0.022* | |
C16 | 0.52900 (15) | 0.45310 (13) | 0.13976 (8) | 0.0168 (3) | |
C17 | 0.75680 (15) | 0.33105 (13) | 0.16409 (8) | 0.0179 (3) | |
C18 | 0.77517 (17) | 0.22589 (14) | 0.12389 (9) | 0.0233 (3) | |
H18A | 0.7206 | 0.2173 | 0.0712 | 0.028* | |
C19 | 0.87714 (18) | 0.13282 (15) | 0.16385 (10) | 0.0285 (4) | |
H19A | 0.8896 | 0.0603 | 0.1379 | 0.034* | |
C20 | 0.95985 (18) | 0.14733 (16) | 0.24163 (10) | 0.0313 (4) | |
H20A | 1.0289 | 0.0853 | 0.2677 | 0.038* | |
C21 | 0.94077 (18) | 0.25331 (16) | 0.28107 (10) | 0.0299 (4) | |
H21A | 0.9970 | 0.2628 | 0.3335 | 0.036* | |
C22 | 0.83737 (16) | 0.34590 (14) | 0.24236 (9) | 0.0227 (3) | |
H22A | 0.8226 | 0.4168 | 0.2687 | 0.027* | |
C23 | 0.47307 (18) | 0.50570 (15) | 0.28774 (9) | 0.0262 (3) | |
H23A | 0.5320 | 0.4453 | 0.3258 | 0.039* | |
H23D | 0.4146 | 0.5542 | 0.3083 | 0.039* | |
H23B | 0.5344 | 0.5635 | 0.2743 | 0.039* | |
C24 | 0.28358 (18) | 0.33466 (15) | 0.23837 (10) | 0.0267 (3) | |
H24D | 0.3466 | 0.2730 | 0.2738 | 0.040* | |
H24A | 0.2189 | 0.2907 | 0.1930 | 0.040* | |
H24B | 0.2281 | 0.3789 | 0.2625 | 0.040* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0270 (6) | 0.0222 (5) | 0.0408 (6) | 0.0090 (4) | 0.0211 (5) | 0.0088 (5) |
O2 | 0.0330 (6) | 0.0195 (5) | 0.0423 (7) | 0.0108 (5) | 0.0219 (5) | 0.0095 (5) |
O3 | 0.0316 (7) | 0.0221 (5) | 0.0662 (9) | 0.0117 (5) | 0.0309 (6) | 0.0124 (6) |
N1 | 0.0182 (6) | 0.0132 (5) | 0.0197 (6) | 0.0024 (4) | 0.0085 (5) | 0.0021 (4) |
C1 | 0.0164 (7) | 0.0144 (6) | 0.0181 (6) | 0.0015 (5) | 0.0061 (5) | 0.0005 (5) |
C2 | 0.0182 (7) | 0.0177 (6) | 0.0200 (7) | 0.0016 (5) | 0.0070 (6) | 0.0002 (5) |
C3 | 0.0179 (7) | 0.0172 (6) | 0.0168 (6) | −0.0006 (5) | 0.0055 (5) | −0.0006 (5) |
C4 | 0.0199 (7) | 0.0224 (7) | 0.0233 (7) | 0.0000 (6) | 0.0094 (6) | −0.0001 (6) |
C5 | 0.0256 (8) | 0.0258 (7) | 0.0287 (8) | −0.0055 (6) | 0.0139 (7) | 0.0001 (6) |
C6 | 0.0292 (8) | 0.0196 (7) | 0.0285 (8) | −0.0049 (6) | 0.0119 (7) | 0.0028 (6) |
C7 | 0.0254 (8) | 0.0157 (6) | 0.0224 (7) | 0.0001 (5) | 0.0089 (6) | 0.0001 (5) |
C8 | 0.0201 (7) | 0.0150 (6) | 0.0169 (6) | −0.0004 (5) | 0.0054 (5) | −0.0009 (5) |
C9 | 0.0198 (7) | 0.0158 (6) | 0.0184 (6) | 0.0020 (5) | 0.0070 (5) | 0.0002 (5) |
C10 | 0.0174 (7) | 0.0146 (6) | 0.0171 (6) | 0.0015 (5) | 0.0065 (5) | −0.0005 (5) |
C11 | 0.0172 (7) | 0.0146 (6) | 0.0194 (6) | 0.0013 (5) | 0.0069 (5) | −0.0009 (5) |
C12 | 0.0199 (7) | 0.0182 (6) | 0.0268 (7) | 0.0024 (5) | 0.0110 (6) | −0.0001 (6) |
C13 | 0.0200 (7) | 0.0201 (7) | 0.0297 (8) | 0.0014 (5) | 0.0135 (6) | 0.0018 (6) |
C14 | 0.0211 (7) | 0.0169 (6) | 0.0248 (7) | −0.0002 (5) | 0.0130 (6) | −0.0015 (5) |
C15 | 0.0180 (7) | 0.0158 (6) | 0.0236 (7) | −0.0006 (5) | 0.0102 (6) | 0.0000 (5) |
C16 | 0.0165 (7) | 0.0152 (6) | 0.0192 (6) | 0.0006 (5) | 0.0075 (5) | −0.0013 (5) |
C17 | 0.0159 (7) | 0.0143 (6) | 0.0247 (7) | 0.0022 (5) | 0.0093 (6) | 0.0050 (5) |
C18 | 0.0231 (8) | 0.0204 (7) | 0.0277 (8) | 0.0038 (6) | 0.0112 (6) | 0.0011 (6) |
C19 | 0.0318 (9) | 0.0191 (7) | 0.0425 (9) | 0.0096 (6) | 0.0232 (8) | 0.0074 (7) |
C20 | 0.0254 (8) | 0.0310 (8) | 0.0430 (10) | 0.0135 (7) | 0.0195 (8) | 0.0204 (7) |
C21 | 0.0227 (8) | 0.0362 (9) | 0.0279 (8) | 0.0055 (7) | 0.0067 (7) | 0.0120 (7) |
C22 | 0.0205 (7) | 0.0225 (7) | 0.0254 (7) | 0.0009 (6) | 0.0093 (6) | 0.0030 (6) |
C23 | 0.0347 (9) | 0.0212 (7) | 0.0248 (7) | −0.0019 (6) | 0.0139 (7) | −0.0028 (6) |
C24 | 0.0306 (8) | 0.0218 (7) | 0.0340 (8) | −0.0012 (6) | 0.0192 (7) | 0.0012 (6) |
O1—C2 | 1.2244 (17) | C13—H13A | 0.9700 |
O2—C9 | 1.2176 (17) | C13—H13B | 0.9700 |
O3—C12 | 1.2187 (17) | C14—C23 | 1.530 (2) |
N1—C16 | 1.3693 (18) | C14—C24 | 1.530 (2) |
N1—C1 | 1.3839 (17) | C14—C15 | 1.5398 (19) |
N1—C17 | 1.4505 (17) | C15—C16 | 1.4901 (19) |
C1—C10 | 1.3822 (18) | C15—H15A | 0.9700 |
C1—C2 | 1.4622 (19) | C15—H15B | 0.9700 |
C2—C3 | 1.4942 (19) | C17—C18 | 1.378 (2) |
C3—C4 | 1.391 (2) | C17—C22 | 1.382 (2) |
C3—C8 | 1.4052 (19) | C18—C19 | 1.391 (2) |
C4—C5 | 1.389 (2) | C18—H18A | 0.9300 |
C4—H4A | 0.9300 | C19—C20 | 1.378 (2) |
C5—C6 | 1.389 (2) | C19—H19A | 0.9300 |
C5—H5A | 0.9300 | C20—C21 | 1.379 (2) |
C6—C7 | 1.387 (2) | C20—H20A | 0.9300 |
C6—H6A | 0.9300 | C21—C22 | 1.390 (2) |
C7—C8 | 1.3963 (19) | C21—H21A | 0.9300 |
C7—H7A | 0.9300 | C22—H22A | 0.9300 |
C8—C9 | 1.496 (2) | C23—H23A | 0.9600 |
C9—C10 | 1.4691 (18) | C23—H23D | 0.9600 |
C10—C11 | 1.4362 (19) | C23—H23B | 0.9600 |
C11—C16 | 1.3905 (18) | C24—H24D | 0.9600 |
C11—C12 | 1.4745 (19) | C24—H24A | 0.9600 |
C12—C13 | 1.513 (2) | C24—H24B | 0.9600 |
C13—C14 | 1.541 (2) | ||
C16—N1—C1 | 108.59 (11) | C23—C14—C24 | 109.19 (12) |
C16—N1—C17 | 123.82 (11) | C23—C14—C15 | 109.86 (12) |
C1—N1—C17 | 125.47 (11) | C24—C14—C15 | 109.29 (12) |
C10—C1—N1 | 108.68 (12) | C23—C14—C13 | 110.58 (12) |
C10—C1—C2 | 125.34 (12) | C24—C14—C13 | 108.87 (12) |
N1—C1—C2 | 125.98 (12) | C15—C14—C13 | 109.02 (12) |
O1—C2—C1 | 123.46 (13) | C16—C15—C14 | 110.52 (11) |
O1—C2—C3 | 121.92 (13) | C16—C15—H15A | 109.5 |
C1—C2—C3 | 114.62 (12) | C14—C15—H15A | 109.5 |
C4—C3—C8 | 119.99 (13) | C16—C15—H15B | 109.5 |
C4—C3—C2 | 118.80 (13) | C14—C15—H15B | 109.5 |
C8—C3—C2 | 121.21 (12) | H15A—C15—H15B | 108.1 |
C5—C4—C3 | 119.96 (14) | N1—C16—C11 | 109.22 (12) |
C5—C4—H4A | 120.0 | N1—C16—C15 | 124.55 (12) |
C3—C4—H4A | 120.0 | C11—C16—C15 | 126.24 (12) |
C4—C5—C6 | 120.21 (14) | C18—C17—C22 | 121.62 (13) |
C4—C5—H5A | 119.9 | C18—C17—N1 | 121.47 (13) |
C6—C5—H5A | 119.9 | C22—C17—N1 | 116.91 (12) |
C7—C6—C5 | 120.32 (14) | C17—C18—C19 | 118.57 (14) |
C7—C6—H6A | 119.8 | C17—C18—H18A | 120.7 |
C5—C6—H6A | 119.8 | C19—C18—H18A | 120.7 |
C6—C7—C8 | 120.00 (14) | C20—C19—C18 | 120.46 (15) |
C6—C7—H7A | 120.0 | C20—C19—H19A | 119.8 |
C8—C7—H7A | 120.0 | C18—C19—H19A | 119.8 |
C7—C8—C3 | 119.52 (13) | C19—C20—C21 | 120.35 (14) |
C7—C8—C9 | 118.40 (13) | C19—C20—H20A | 119.8 |
C3—C8—C9 | 122.08 (12) | C21—C20—H20A | 119.8 |
O2—C9—C10 | 123.31 (13) | C20—C21—C22 | 119.93 (15) |
O2—C9—C8 | 120.47 (13) | C20—C21—H21A | 120.0 |
C10—C9—C8 | 116.21 (12) | C22—C21—H21A | 120.0 |
C1—C10—C11 | 107.15 (12) | C17—C22—C21 | 119.05 (14) |
C1—C10—C9 | 120.38 (12) | C17—C22—H22A | 120.5 |
C11—C10—C9 | 132.31 (12) | C21—C22—H22A | 120.5 |
C16—C11—C10 | 106.36 (12) | C14—C23—H23A | 109.5 |
C16—C11—C12 | 119.88 (13) | C14—C23—H23D | 109.5 |
C10—C11—C12 | 133.65 (12) | H23A—C23—H23D | 109.5 |
O3—C12—C11 | 124.19 (14) | C14—C23—H23B | 109.5 |
O3—C12—C13 | 121.06 (13) | H23A—C23—H23B | 109.5 |
C11—C12—C13 | 114.75 (12) | H23D—C23—H23B | 109.5 |
C12—C13—C14 | 115.95 (12) | C14—C24—H24D | 109.5 |
C12—C13—H13A | 108.3 | C14—C24—H24A | 109.5 |
C14—C13—H13A | 108.3 | H24D—C24—H24A | 109.5 |
C12—C13—H13B | 108.3 | C14—C24—H24B | 109.5 |
C14—C13—H13B | 108.3 | H24D—C24—H24B | 109.5 |
H13A—C13—H13B | 107.4 | H24A—C24—H24B | 109.5 |
C16—N1—C1—C10 | 0.16 (15) | C1—C10—C11—C12 | 176.89 (15) |
C17—N1—C1—C10 | −163.70 (12) | C9—C10—C11—C12 | 1.6 (3) |
C16—N1—C1—C2 | −179.09 (13) | C16—C11—C12—O3 | 173.72 (15) |
C17—N1—C1—C2 | 17.0 (2) | C10—C11—C12—O3 | −1.9 (3) |
C10—C1—C2—O1 | −176.81 (14) | C16—C11—C12—C13 | −6.89 (19) |
N1—C1—C2—O1 | 2.3 (2) | C10—C11—C12—C13 | 177.52 (14) |
C10—C1—C2—C3 | 3.6 (2) | O3—C12—C13—C14 | −146.12 (15) |
N1—C1—C2—C3 | −177.25 (12) | C11—C12—C13—C14 | 34.47 (18) |
O1—C2—C3—C4 | −1.0 (2) | C12—C13—C14—C23 | 65.39 (16) |
C1—C2—C3—C4 | 178.52 (13) | C12—C13—C14—C24 | −174.65 (12) |
O1—C2—C3—C8 | 179.56 (14) | C12—C13—C14—C15 | −55.50 (16) |
C1—C2—C3—C8 | −0.87 (19) | C23—C14—C15—C16 | −73.91 (15) |
C8—C3—C4—C5 | −0.3 (2) | C24—C14—C15—C16 | 166.31 (12) |
C2—C3—C4—C5 | −179.67 (13) | C13—C14—C15—C16 | 47.42 (15) |
C3—C4—C5—C6 | −0.1 (2) | C1—N1—C16—C11 | 0.41 (15) |
C4—C5—C6—C7 | 0.5 (2) | C17—N1—C16—C11 | 164.60 (12) |
C5—C6—C7—C8 | −0.4 (2) | C1—N1—C16—C15 | −179.61 (13) |
C6—C7—C8—C3 | 0.0 (2) | C17—N1—C16—C15 | −15.4 (2) |
C6—C7—C8—C9 | 179.64 (13) | C10—C11—C16—N1 | −0.79 (15) |
C4—C3—C8—C7 | 0.3 (2) | C12—C11—C16—N1 | −177.47 (12) |
C2—C3—C8—C7 | 179.69 (12) | C10—C11—C16—C15 | 179.23 (13) |
C4—C3—C8—C9 | −179.28 (13) | C12—C11—C16—C15 | 2.6 (2) |
C2—C3—C8—C9 | 0.1 (2) | C14—C15—C16—N1 | 155.83 (13) |
C7—C8—C9—O2 | −2.2 (2) | C14—C15—C16—C11 | −24.20 (19) |
C3—C8—C9—O2 | 177.36 (14) | C16—N1—C17—C18 | 111.91 (16) |
C7—C8—C9—C10 | 178.78 (12) | C1—N1—C17—C18 | −86.59 (17) |
C3—C8—C9—C10 | −1.62 (19) | C16—N1—C17—C22 | −68.08 (17) |
N1—C1—C10—C11 | −0.64 (15) | C1—N1—C17—C22 | 93.42 (16) |
C2—C1—C10—C11 | 178.62 (13) | C22—C17—C18—C19 | 0.3 (2) |
N1—C1—C10—C9 | 175.32 (12) | N1—C17—C18—C19 | −179.65 (13) |
C2—C1—C10—C9 | −5.4 (2) | C17—C18—C19—C20 | −1.3 (2) |
O2—C9—C10—C1 | −174.82 (14) | C18—C19—C20—C21 | 1.1 (2) |
C8—C9—C10—C1 | 4.13 (19) | C19—C20—C21—C22 | 0.2 (2) |
O2—C9—C10—C11 | 0.0 (2) | C18—C17—C22—C21 | 0.9 (2) |
C8—C9—C10—C11 | 178.92 (14) | N1—C17—C22—C21 | −179.09 (13) |
C1—C10—C11—C16 | 0.88 (15) | C20—C21—C22—C17 | −1.2 (2) |
C9—C10—C11—C16 | −174.42 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···O1i | 0.93 | 2.59 | 3.360 (2) | 140 |
C7—H7A···O2ii | 0.93 | 2.37 | 3.272 (2) | 163 |
C18—H18A···O2iii | 0.93 | 2.40 | 3.262 (2) | 155 |
C15—H15B···Cg1iii | 0.97 | 2.82 | 3.742 (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 formula | C24H19NO3 |
Mr | 369.40 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 105 |
a, b, c (Å) | 10.0097 (4), 10.3559 (3), 18.8030 (6) |
β (°) | 113.032 (2) |
V (Å3) | 1793.74 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.44 × 0.44 × 0.21 |
Data collection | |
Diffractometer | Bruker SMART APEX II CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.923, 0.981 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20016, 5227, 3937 |
Rint | 0.045 |
(sin θ/λ)max (Å−1) | 0.703 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.131, 1.04 |
No. of reflections | 5227 |
No. of parameters | 255 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.40, −0.25 |
Computer programs: APEX2 (Bruker, 2005), APEX2, SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···O1i | 0.93 | 2.59 | 3.360 (2) | 140 |
C7—H7A···O2ii | 0.93 | 2.37 | 3.272 (2) | 163 |
C18—H18A···O2iii | 0.93 | 2.40 | 3.262 (2) | 155 |
C15—H15B···Cg1iii | 0.97 | 2.82 | 3.742 (2) | 158 |
Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+1, −y+2, −z; (iii) −x+1, −y+1, −z. |
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.