Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807028334/om2133sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807028334/om2133Isup2.hkl |
CCDC reference: 654977
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.045
- wR factor = 0.125
- Data-to-parameter ratio = 21.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 300 Deg. PLAT333_ALERT_2_C Large Average Benzene C-C Dist. C4 -C13 1.45 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Cl2 .. O4 .. 3.22 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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
For values of bond lengths and angles, see Allen et al. (1987). For ring conformations, see Cremer & Pople (1975). For related structures, see for example, Fun et al. (2007). For naturally occurring quinones and activities, see for example, Patai & Rappoport (1988); Thomson (1997); Bolton et al. (2000); Hu et al. (2006); Fun et al. (2007).
A mixture of 2,3-dichloro-1,4-naphthoquinone (1.1 mmol), 3-(4-methoxyphenylamino)-5,5-dimethylcyclohex-2-enone (1 mmol) and Na2CO3 (2.5 mmol) in dimethylformamide (15 ml) was stirred at 353 K for 6 h. After evaporation of the solvent, the title compound was isolated using silica-gel column chromatography with petroleum ether-ethyl acetate (4:1) as eluents (yield 83%). Single crystals of the title compound in yellow block shape were obtained by slow evaporation of a petroleum ether/ethyl acetate (3:1 v/v) solution of the title compound; m. p. 531–533 K.
All H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H distances in the range 0.93–0.98 Å. The Uiso values were constrained to be 1.5Ueq of the carrier atom for methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups. The highest residual peak is located 0.75 Å from Cl3 and the deepest hole is located 0.69 Å from Cl3.
Naturally occurring quinones constitute an important class of natural products (Patai & Rappoport, 1988; Thomson, 1997) that have a wide range of biological activities (Bolton et al., 2000). A basic structural unit in these quinine natural products is the indolequinone moiety. Synthesis of the benzannulated indolequinones, benzo[b]carbazole-6,11-dione, attracts much current attention (Hu et al., 2006). As an extension of our research on the direct one-pot syntheses of benzo[b]carbazole-6,11-dione derivatives, the title compound was synthesized by a C,N-dialkylation reaction between 2,3-dichloro-1,4-naphthoquinone and 3-(4-methoxyphenylamino)-5,5- dimethylcyclohex-2-enone. An X-ray crystallographic analysis was undertaken to elucidate its three-dimensional structure.
In the asymmetric unit of the title compound in Fig. 1, the indolequinone moiety [N1/O2–O3/C3–C14] is essentially planar with atom C12 having the maximum deviation of 0.094 (1) Å and the cyclohexene-1-one ring [O4/C1–C3/C14–C16 ring adopts an envelope conformation (Cremer & Pople, 1975) with atom C1 displaced from the C2–C3/C14–C16 mean plane by -0.3155 (17) Å and with the puckering parameters Q = 0.454 (2) Å, θ = 132.1 (4)° and φ = 169.3 (3)°. The methoxy group is slightly deviated from the plane of C17–C22 benzene ring as indicated by the torsion angle C19/C20/O1/C23 = 4.5 (2)°. The methoxyphenyl is almost perpendicularly attached at atom N1, the dihedral angle between the indole and methoxyphenyl rings is 81.78 (8)°. All bond lengths and angles are in normal ranges (Allen et al., 1987).
The crystal packing (Fig. 2) shows that the molecules are linked via weak C10—H10A···O3 [symmetry code; -1 - x, 2 - y, 2 - z] and C18—H18A···O3 [symmetry code; -x, 2 - y, 2 - z] weak interactions to form dimers and these dimers are arranged into chains running approximately along the b axis (Fig. 2). The crystal is stabilized by weak C—H···O intermolecular interactions and C—H···π interactions (Table 1); Cg1 and Cg2 are the centroids of C6–C11 and C17–C22 benzene rings, respectively.
For values of bond lengths and angles, see Allen et al. (1987). For ring conformations, see Cremer & Pople (1975). For related structures, see for example, Fun et al. (2007). For naturally occurring quinones and activities, see for example, Patai & Rappoport (1988); Thomson (1997); Bolton et al. (2000); 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 and PLATON (Spek, 2003).
C25H21NO4·CHCl3 | Z = 2 |
Mr = 518.80 | F(000) = 536 |
Triclinic, P1 | Dx = 1.466 Mg m−3 |
Hall symbol: -P 1 | Melting point = 531–533 K |
a = 8.9167 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.1639 (5) Å | Cell parameters from 6780 reflections |
c = 14.3550 (8) Å | θ = 2.2–30.0° |
α = 71.547 (3)° | µ = 0.43 mm−1 |
β = 72.281 (3)° | T = 100 K |
γ = 85.367 (3)° | Block, yellow |
V = 1175.36 (11) Å3 | 0.58 × 0.34 × 0.24 mm |
Bruker SMART APEXII CCD area-detector diffractometer | 6780 independent reflections |
Radiation source: fine-focus sealed tube | 5521 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
Detector resolution: 8.33 pixels mm-1 | θmax = 30.0°, θmin = 2.2° |
ω scans | h = −12→12 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −14→14 |
Tmin = 0.791, Tmax = 0.903 | l = −20→20 |
16460 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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.125 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0639P)2 + 0.385P] where P = (Fo2 + 2Fc2)/3 |
6780 reflections | (Δ/σ)max = 0.001 |
310 parameters | Δρmax = 0.59 e Å−3 |
0 restraints | Δρmin = −0.48 e Å−3 |
C25H21NO4·CHCl3 | γ = 85.367 (3)° |
Mr = 518.80 | V = 1175.36 (11) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.9167 (5) Å | Mo Kα radiation |
b = 10.1639 (5) Å | µ = 0.43 mm−1 |
c = 14.3550 (8) Å | T = 100 K |
α = 71.547 (3)° | 0.58 × 0.34 × 0.24 mm |
β = 72.281 (3)° |
Bruker SMART APEXII CCD area-detector diffractometer | 6780 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 5521 reflections with I > 2σ(I) |
Tmin = 0.791, Tmax = 0.903 | Rint = 0.038 |
16460 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.125 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.59 e Å−3 |
6780 reflections | Δρmin = −0.48 e Å−3 |
310 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 | ||
Cl1 | 0.23402 (7) | 0.79707 (5) | 0.48120 (3) | 0.03451 (13) | |
Cl2 | 0.24023 (5) | 0.79013 (5) | 0.27970 (4) | 0.02991 (12) | |
Cl3 | 0.04991 (6) | 0.99133 (5) | 0.36617 (4) | 0.03617 (13) | |
C26 | 0.2247 (2) | 0.89613 (18) | 0.35806 (13) | 0.0234 (3) | |
H26A | 0.3139 | 0.9620 | 0.3264 | 0.028* | |
O3 | −0.27979 (13) | 1.05545 (11) | 0.98946 (9) | 0.0188 (2) | |
O4 | −0.11827 (14) | 1.32503 (12) | 0.86984 (10) | 0.0232 (3) | |
N1 | 0.21722 (15) | 0.97595 (12) | 0.79625 (9) | 0.0133 (2) | |
C1 | 0.27863 (18) | 1.36341 (15) | 0.69063 (11) | 0.0158 (3) | |
C2 | 0.34101 (18) | 1.21556 (15) | 0.72643 (11) | 0.0161 (3) | |
H2A | 0.4042 | 1.1894 | 0.6671 | 0.019* | |
H2B | 0.4076 | 1.2138 | 0.7691 | 0.019* | |
C3 | 0.20809 (17) | 1.11473 (14) | 0.78568 (11) | 0.0135 (3) | |
C4 | 0.07375 (17) | 0.91363 (14) | 0.85738 (10) | 0.0132 (3) | |
C5 | 0.03251 (18) | 0.76871 (15) | 0.87948 (11) | 0.0155 (3) | |
C6 | −0.13426 (18) | 0.72965 (15) | 0.94308 (11) | 0.0148 (3) | |
C7 | −0.18473 (19) | 0.59248 (15) | 0.96924 (12) | 0.0172 (3) | |
H7A | −0.1148 | 0.5272 | 0.9483 | 0.021* | |
C8 | −0.3395 (2) | 0.55401 (16) | 1.02656 (12) | 0.0195 (3) | |
H8A | −0.3727 | 0.4624 | 1.0450 | 0.023* | |
C9 | −0.44544 (19) | 0.65209 (17) | 1.05668 (12) | 0.0194 (3) | |
H9A | −0.5497 | 0.6263 | 1.0934 | 0.023* | |
C10 | −0.39547 (18) | 0.78851 (16) | 1.03195 (11) | 0.0173 (3) | |
H10A | −0.4661 | 0.8534 | 1.0529 | 0.021* | |
C11 | −0.23914 (17) | 0.82815 (15) | 0.97570 (11) | 0.0139 (3) | |
C12 | −0.18920 (17) | 0.97554 (15) | 0.95264 (11) | 0.0138 (3) | |
C13 | −0.02768 (17) | 1.01407 (14) | 0.88585 (11) | 0.0129 (3) | |
C14 | 0.05774 (17) | 1.14358 (14) | 0.83969 (11) | 0.0132 (3) | |
C15 | 0.01523 (18) | 1.28831 (15) | 0.83443 (11) | 0.0151 (3) | |
C16 | 0.15193 (19) | 1.39154 (15) | 0.78256 (12) | 0.0167 (3) | |
H16A | 0.2021 | 1.3928 | 0.8335 | 0.020* | |
H16B | 0.1103 | 1.4832 | 0.7590 | 0.020* | |
C17 | 0.35632 (17) | 0.90683 (14) | 0.75367 (11) | 0.0137 (3) | |
C18 | 0.45051 (18) | 0.83945 (15) | 0.81394 (11) | 0.0164 (3) | |
H18A | 0.4260 | 0.8409 | 0.8814 | 0.020* | |
C19 | 0.58302 (18) | 0.76889 (16) | 0.77371 (12) | 0.0178 (3) | |
H19A | 0.6470 | 0.7234 | 0.8141 | 0.021* | |
C20 | 0.61841 (18) | 0.76729 (15) | 0.67262 (12) | 0.0166 (3) | |
C21 | 0.52359 (19) | 0.83835 (16) | 0.61160 (12) | 0.0191 (3) | |
H21A | 0.5487 | 0.8389 | 0.5437 | 0.023* | |
C22 | 0.39252 (18) | 0.90782 (15) | 0.65204 (11) | 0.0167 (3) | |
H22A | 0.3291 | 0.9548 | 0.6116 | 0.020* | |
C23 | 0.8358 (2) | 0.6179 (2) | 0.68665 (15) | 0.0313 (4) | |
H23A | 0.9141 | 0.5713 | 0.6464 | 0.047* | |
H23B | 0.7698 | 0.5506 | 0.7453 | 0.047* | |
H23C | 0.8865 | 0.6765 | 0.7094 | 0.047* | |
C24 | 0.4156 (2) | 1.46772 (16) | 0.65440 (13) | 0.0219 (3) | |
H24A | 0.4970 | 1.4486 | 0.5989 | 0.033* | |
H24B | 0.4570 | 1.4595 | 0.7104 | 0.033* | |
H24C | 0.3785 | 1.5601 | 0.6313 | 0.033* | |
C25 | 0.2105 (2) | 1.37711 (16) | 0.60257 (12) | 0.0204 (3) | |
H25A | 0.2907 | 1.3582 | 0.5465 | 0.031* | |
H25B | 0.1733 | 1.4696 | 0.5801 | 0.031* | |
H25C | 0.1246 | 1.3121 | 0.6258 | 0.031* | |
O1 | 0.74217 (14) | 0.70017 (13) | 0.62578 (9) | 0.0232 (3) | |
O2 | 0.12306 (14) | 0.68601 (12) | 0.84612 (10) | 0.0236 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0441 (3) | 0.0347 (2) | 0.0262 (2) | 0.0059 (2) | −0.01755 (19) | −0.00567 (17) |
Cl2 | 0.0242 (2) | 0.0402 (2) | 0.0363 (2) | 0.00893 (18) | −0.01432 (17) | −0.02350 (19) |
Cl3 | 0.0386 (3) | 0.0423 (3) | 0.0352 (2) | 0.0203 (2) | −0.0178 (2) | −0.0204 (2) |
C26 | 0.0266 (8) | 0.0230 (7) | 0.0231 (7) | 0.0032 (7) | −0.0114 (6) | −0.0076 (6) |
O3 | 0.0156 (5) | 0.0176 (5) | 0.0237 (5) | 0.0040 (4) | −0.0034 (4) | −0.0099 (4) |
O4 | 0.0182 (5) | 0.0169 (5) | 0.0336 (6) | 0.0049 (4) | −0.0032 (5) | −0.0119 (4) |
N1 | 0.0127 (5) | 0.0117 (5) | 0.0159 (5) | 0.0022 (4) | −0.0041 (4) | −0.0051 (4) |
C1 | 0.0175 (7) | 0.0121 (6) | 0.0175 (6) | 0.0011 (5) | −0.0051 (5) | −0.0044 (5) |
C2 | 0.0140 (6) | 0.0140 (6) | 0.0191 (6) | 0.0015 (5) | −0.0038 (5) | −0.0046 (5) |
C3 | 0.0146 (6) | 0.0118 (6) | 0.0157 (6) | 0.0027 (5) | −0.0064 (5) | −0.0053 (5) |
C4 | 0.0130 (6) | 0.0127 (6) | 0.0145 (6) | 0.0023 (5) | −0.0042 (5) | −0.0054 (5) |
C5 | 0.0160 (6) | 0.0135 (6) | 0.0183 (6) | 0.0022 (5) | −0.0056 (5) | −0.0064 (5) |
C6 | 0.0152 (6) | 0.0141 (6) | 0.0161 (6) | 0.0004 (5) | −0.0055 (5) | −0.0053 (5) |
C7 | 0.0205 (7) | 0.0144 (6) | 0.0194 (6) | 0.0008 (5) | −0.0088 (6) | −0.0063 (5) |
C8 | 0.0213 (7) | 0.0179 (7) | 0.0216 (7) | −0.0034 (6) | −0.0094 (6) | −0.0053 (5) |
C9 | 0.0161 (7) | 0.0238 (7) | 0.0189 (7) | −0.0026 (6) | −0.0064 (6) | −0.0053 (6) |
C10 | 0.0141 (7) | 0.0213 (7) | 0.0175 (6) | 0.0017 (6) | −0.0059 (5) | −0.0067 (5) |
C11 | 0.0129 (6) | 0.0156 (6) | 0.0139 (6) | 0.0010 (5) | −0.0045 (5) | −0.0050 (5) |
C12 | 0.0145 (6) | 0.0151 (6) | 0.0139 (6) | 0.0034 (5) | −0.0061 (5) | −0.0061 (5) |
C13 | 0.0128 (6) | 0.0128 (6) | 0.0146 (6) | 0.0014 (5) | −0.0049 (5) | −0.0057 (5) |
C14 | 0.0136 (6) | 0.0117 (6) | 0.0165 (6) | 0.0028 (5) | −0.0056 (5) | −0.0069 (5) |
C15 | 0.0186 (7) | 0.0126 (6) | 0.0167 (6) | 0.0035 (5) | −0.0071 (5) | −0.0066 (5) |
C16 | 0.0193 (7) | 0.0117 (6) | 0.0201 (6) | 0.0014 (5) | −0.0059 (6) | −0.0065 (5) |
C17 | 0.0133 (6) | 0.0116 (6) | 0.0168 (6) | 0.0030 (5) | −0.0043 (5) | −0.0060 (5) |
C18 | 0.0179 (7) | 0.0166 (6) | 0.0158 (6) | 0.0050 (5) | −0.0056 (5) | −0.0073 (5) |
C19 | 0.0159 (7) | 0.0189 (7) | 0.0199 (7) | 0.0074 (6) | −0.0071 (6) | −0.0075 (5) |
C20 | 0.0141 (6) | 0.0150 (6) | 0.0205 (7) | 0.0032 (5) | −0.0029 (5) | −0.0080 (5) |
C21 | 0.0207 (7) | 0.0206 (7) | 0.0161 (6) | 0.0045 (6) | −0.0038 (6) | −0.0084 (5) |
C22 | 0.0162 (7) | 0.0182 (6) | 0.0171 (6) | 0.0045 (5) | −0.0066 (5) | −0.0067 (5) |
C23 | 0.0262 (9) | 0.0337 (9) | 0.0335 (9) | 0.0189 (8) | −0.0087 (7) | −0.0141 (7) |
C24 | 0.0217 (8) | 0.0165 (7) | 0.0248 (7) | −0.0030 (6) | −0.0048 (6) | −0.0040 (6) |
C25 | 0.0248 (8) | 0.0192 (7) | 0.0178 (6) | 0.0027 (6) | −0.0079 (6) | −0.0055 (5) |
O1 | 0.0198 (5) | 0.0269 (6) | 0.0232 (5) | 0.0118 (5) | −0.0045 (5) | −0.0126 (5) |
O2 | 0.0204 (6) | 0.0153 (5) | 0.0331 (6) | 0.0024 (4) | −0.0008 (5) | −0.0120 (4) |
Cl1—C26 | 1.7591 (18) | C10—H10A | 0.9300 |
Cl2—C26 | 1.7588 (18) | C11—C12 | 1.502 (2) |
Cl3—C26 | 1.7598 (18) | C12—C13 | 1.470 (2) |
C26—H26A | 0.9800 | C13—C14 | 1.433 (2) |
O3—C12 | 1.2237 (17) | C14—C15 | 1.4732 (19) |
O4—C15 | 1.2226 (19) | C15—C16 | 1.517 (2) |
N1—C3 | 1.3686 (17) | C16—H16A | 0.9700 |
N1—C4 | 1.3797 (18) | C16—H16B | 0.9700 |
N1—C17 | 1.4404 (17) | C17—C18 | 1.377 (2) |
C1—C25 | 1.526 (2) | C17—C22 | 1.392 (2) |
C1—C24 | 1.536 (2) | C18—C19 | 1.3977 (19) |
C1—C16 | 1.542 (2) | C18—H18A | 0.9300 |
C1—C2 | 1.543 (2) | C19—C20 | 1.393 (2) |
C2—C3 | 1.486 (2) | C19—H19A | 0.9300 |
C2—H2A | 0.9700 | C20—O1 | 1.3611 (17) |
C2—H2B | 0.9700 | C20—C21 | 1.398 (2) |
C3—C14 | 1.3900 (19) | C21—C22 | 1.384 (2) |
C4—C13 | 1.3845 (18) | C21—H21A | 0.9300 |
C4—C5 | 1.458 (2) | C22—H22A | 0.9300 |
C5—O2 | 1.2238 (17) | C23—O1 | 1.424 (2) |
C5—C6 | 1.497 (2) | C23—H23A | 0.9600 |
C6—C7 | 1.398 (2) | C23—H23B | 0.9600 |
C6—C11 | 1.4054 (19) | C23—H23C | 0.9600 |
C7—C8 | 1.388 (2) | C24—H24A | 0.9600 |
C7—H7A | 0.9300 | C24—H24B | 0.9600 |
C8—C9 | 1.395 (2) | C24—H24C | 0.9600 |
C8—H8A | 0.9300 | C25—H25A | 0.9600 |
C9—C10 | 1.392 (2) | C25—H25B | 0.9600 |
C9—H9A | 0.9300 | C25—H25C | 0.9600 |
C10—C11 | 1.399 (2) | ||
Cl2—C26—Cl1 | 111.01 (9) | C4—C13—C12 | 120.10 (13) |
Cl2—C26—Cl3 | 110.59 (10) | C14—C13—C12 | 132.78 (12) |
Cl1—C26—Cl3 | 110.73 (9) | C3—C14—C13 | 106.38 (12) |
Cl2—C26—H26A | 108.1 | C3—C14—C15 | 119.49 (13) |
Cl1—C26—H26A | 108.1 | C13—C14—C15 | 134.00 (13) |
Cl3—C26—H26A | 108.1 | O4—C15—C14 | 123.93 (14) |
C3—N1—C4 | 108.67 (11) | O4—C15—C16 | 121.28 (13) |
C3—N1—C17 | 125.14 (12) | C14—C15—C16 | 114.78 (12) |
C4—N1—C17 | 126.15 (12) | C15—C16—C1 | 115.60 (12) |
C25—C1—C24 | 109.86 (13) | C15—C16—H16A | 108.4 |
C25—C1—C16 | 110.76 (13) | C1—C16—H16A | 108.4 |
C24—C1—C16 | 108.88 (13) | C15—C16—H16B | 108.4 |
C25—C1—C2 | 109.91 (13) | C1—C16—H16B | 108.4 |
C24—C1—C2 | 108.67 (13) | H16A—C16—H16B | 107.4 |
C16—C1—C2 | 108.73 (11) | C18—C17—C22 | 120.88 (13) |
C3—C2—C1 | 110.49 (12) | C18—C17—N1 | 119.88 (13) |
C3—C2—H2A | 109.6 | C22—C17—N1 | 119.24 (13) |
C1—C2—H2A | 109.6 | C17—C18—C19 | 119.99 (14) |
C3—C2—H2B | 109.6 | C17—C18—H18A | 120.0 |
C1—C2—H2B | 109.6 | C19—C18—H18A | 120.0 |
H2A—C2—H2B | 108.1 | C20—C19—C18 | 119.46 (14) |
N1—C3—C14 | 109.19 (13) | C20—C19—H19A | 120.3 |
N1—C3—C2 | 124.21 (12) | C18—C19—H19A | 120.3 |
C14—C3—C2 | 126.59 (13) | O1—C20—C19 | 124.76 (14) |
N1—C4—C13 | 108.65 (12) | O1—C20—C21 | 115.24 (13) |
N1—C4—C5 | 125.15 (12) | C19—C20—C21 | 120.00 (13) |
C13—C4—C5 | 125.95 (13) | C22—C21—C20 | 120.16 (14) |
O2—C5—C4 | 123.65 (14) | C22—C21—H21A | 119.9 |
O2—C5—C6 | 121.99 (14) | C20—C21—H21A | 119.9 |
C4—C5—C6 | 114.31 (12) | C21—C22—C17 | 119.48 (14) |
C7—C6—C11 | 120.22 (14) | C21—C22—H22A | 120.3 |
C7—C6—C5 | 118.61 (13) | C17—C22—H22A | 120.3 |
C11—C6—C5 | 121.17 (13) | O1—C23—H23A | 109.5 |
C8—C7—C6 | 119.81 (14) | O1—C23—H23B | 109.5 |
C8—C7—H7A | 120.1 | H23A—C23—H23B | 109.5 |
C6—C7—H7A | 120.1 | O1—C23—H23C | 109.5 |
C7—C8—C9 | 120.29 (15) | H23A—C23—H23C | 109.5 |
C7—C8—H8A | 119.9 | H23B—C23—H23C | 109.5 |
C9—C8—H8A | 119.9 | C1—C24—H24A | 109.5 |
C10—C9—C8 | 120.18 (14) | C1—C24—H24B | 109.5 |
C10—C9—H9A | 119.9 | H24A—C24—H24B | 109.5 |
C8—C9—H9A | 119.9 | C1—C24—H24C | 109.5 |
C9—C10—C11 | 120.11 (14) | H24A—C24—H24C | 109.5 |
C9—C10—H10A | 119.9 | H24B—C24—H24C | 109.5 |
C11—C10—H10A | 119.9 | C1—C25—H25A | 109.5 |
C10—C11—C6 | 119.36 (14) | C1—C25—H25B | 109.5 |
C10—C11—C12 | 118.41 (13) | H25A—C25—H25B | 109.5 |
C6—C11—C12 | 122.24 (13) | C1—C25—H25C | 109.5 |
O3—C12—C13 | 123.66 (13) | H25A—C25—H25C | 109.5 |
O3—C12—C11 | 120.47 (13) | H25B—C25—H25C | 109.5 |
C13—C12—C11 | 115.86 (12) | C20—O1—C23 | 117.51 (13) |
C4—C13—C14 | 107.12 (12) | ||
C25—C1—C2—C3 | −73.84 (16) | C5—C4—C13—C12 | 6.2 (2) |
C24—C1—C2—C3 | 165.91 (13) | O3—C12—C13—C4 | 172.17 (15) |
C16—C1—C2—C3 | 47.54 (17) | C11—C12—C13—C4 | −7.0 (2) |
C4—N1—C3—C14 | −0.31 (17) | O3—C12—C13—C14 | −7.1 (3) |
C17—N1—C3—C14 | −177.96 (14) | C11—C12—C13—C14 | 173.71 (16) |
C4—N1—C3—C2 | 178.90 (14) | N1—C3—C14—C13 | 0.41 (17) |
C17—N1—C3—C2 | 1.2 (2) | C2—C3—C14—C13 | −178.77 (15) |
C1—C2—C3—N1 | 155.67 (14) | N1—C3—C14—C15 | −175.94 (13) |
C1—C2—C3—C14 | −25.3 (2) | C2—C3—C14—C15 | 4.9 (2) |
C3—N1—C4—C13 | 0.07 (17) | C4—C13—C14—C3 | −0.37 (17) |
C17—N1—C4—C13 | 177.69 (14) | C12—C13—C14—C3 | 179.00 (16) |
C3—N1—C4—C5 | 174.60 (14) | C4—C13—C14—C15 | 175.22 (16) |
C17—N1—C4—C5 | −7.8 (2) | C12—C13—C14—C15 | −5.4 (3) |
N1—C4—C5—O2 | 0.6 (3) | C3—C14—C15—O4 | 171.65 (15) |
C13—C4—C5—O2 | 174.24 (16) | C13—C14—C15—O4 | −3.5 (3) |
N1—C4—C5—C6 | −176.57 (14) | C3—C14—C15—C16 | −9.4 (2) |
C13—C4—C5—C6 | −3.0 (2) | C13—C14—C15—C16 | 175.42 (16) |
O2—C5—C6—C7 | 3.4 (2) | O4—C15—C16—C1 | −144.74 (15) |
C4—C5—C6—C7 | −179.37 (14) | C14—C15—C16—C1 | 36.32 (19) |
O2—C5—C6—C11 | −176.26 (16) | C25—C1—C16—C15 | 64.85 (17) |
C4—C5—C6—C11 | 1.0 (2) | C24—C1—C16—C15 | −174.25 (13) |
C11—C6—C7—C8 | 0.8 (2) | C2—C1—C16—C15 | −56.02 (18) |
C5—C6—C7—C8 | −178.84 (14) | C3—N1—C17—C18 | 97.14 (18) |
C6—C7—C8—C9 | 1.1 (2) | C4—N1—C17—C18 | −80.1 (2) |
C7—C8—C9—C10 | −1.9 (3) | C3—N1—C17—C22 | −83.6 (2) |
C8—C9—C10—C11 | 0.8 (2) | C4—N1—C17—C22 | 99.11 (18) |
C9—C10—C11—C6 | 1.1 (2) | C22—C17—C18—C19 | −1.1 (2) |
C9—C10—C11—C12 | −178.68 (14) | N1—C17—C18—C19 | 178.14 (14) |
C7—C6—C11—C10 | −1.9 (2) | C17—C18—C19—C20 | −0.1 (2) |
C5—C6—C11—C10 | 177.76 (14) | C18—C19—C20—O1 | −178.73 (15) |
C7—C6—C11—C12 | 177.89 (14) | C18—C19—C20—C21 | 1.3 (2) |
C5—C6—C11—C12 | −2.5 (2) | O1—C20—C21—C22 | 178.64 (15) |
C10—C11—C12—O3 | 5.9 (2) | C19—C20—C21—C22 | −1.4 (2) |
C6—C11—C12—O3 | −173.84 (15) | C20—C21—C22—C17 | 0.3 (2) |
C10—C11—C12—C13 | −174.91 (14) | C18—C17—C22—C21 | 1.0 (2) |
C6—C11—C12—C13 | 5.3 (2) | N1—C17—C22—C21 | −178.23 (14) |
N1—C4—C13—C14 | 0.19 (17) | C19—C20—O1—C23 | 4.5 (2) |
C5—C4—C13—C14 | −174.29 (14) | C21—C20—O1—C23 | −175.56 (16) |
N1—C4—C13—C12 | −179.28 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10A···O3i | 0.93 | 2.55 | 3.238 (2) | 131 |
C18—H18A···O3ii | 0.93 | 2.41 | 3.2333 (19) | 148 |
C16—H16A···Cg1ii | 0.97 | 2.60 | 3.5242 (18) | 160 |
C19—H19A···Cg1iii | 0.93 | 2.81 | 3.6035 (17) | 143 |
C26—H26A···Cg2iv | 0.98 | 2.61 | 3.565 (2) | 164 |
Symmetry codes: (i) −x−1, −y+2, −z+2; (ii) −x, −y+2, −z+2; (iii) x+1, y, z; (iv) −x+1, −y+2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C25H21NO4·CHCl3 |
Mr | 518.80 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 8.9167 (5), 10.1639 (5), 14.3550 (8) |
α, β, γ (°) | 71.547 (3), 72.281 (3), 85.367 (3) |
V (Å3) | 1175.36 (11) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.43 |
Crystal size (mm) | 0.58 × 0.34 × 0.24 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.791, 0.903 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16460, 6780, 5521 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.703 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.125, 1.05 |
No. of reflections | 6780 |
No. of parameters | 310 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.59, −0.48 |
Computer programs: APEX2 (Bruker, 2005), APEX2, SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998), SHELXTL and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10A···O3i | 0.93 | 2.5505 | 3.238 (2) | 131 |
C18—H18A···O3ii | 0.93 | 2.4061 | 3.2333 (19) | 148 |
C16—H16A···Cg1ii | 0.97 | 2.5988 | 3.5242 (18) | 160 |
C19—H19A···Cg1iii | 0.93 | 2.8137 | 3.6035 (17) | 143 |
C26—H26A···Cg2iv | 0.98 | 2.6139 | 3.565 (2) | 164 |
Symmetry codes: (i) −x−1, −y+2, −z+2; (ii) −x, −y+2, −z+2; (iii) x+1, y, z; (iv) −x+1, −y+2, −z+1. |
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Naturally occurring quinones constitute an important class of natural products (Patai & Rappoport, 1988; Thomson, 1997) that have a wide range of biological activities (Bolton et al., 2000). A basic structural unit in these quinine natural products is the indolequinone moiety. Synthesis of the benzannulated indolequinones, benzo[b]carbazole-6,11-dione, attracts much current attention (Hu et al., 2006). As an extension of our research on the direct one-pot syntheses of benzo[b]carbazole-6,11-dione derivatives, the title compound was synthesized by a C,N-dialkylation reaction between 2,3-dichloro-1,4-naphthoquinone and 3-(4-methoxyphenylamino)-5,5- dimethylcyclohex-2-enone. An X-ray crystallographic analysis was undertaken to elucidate its three-dimensional structure.
In the asymmetric unit of the title compound in Fig. 1, the indolequinone moiety [N1/O2–O3/C3–C14] is essentially planar with atom C12 having the maximum deviation of 0.094 (1) Å and the cyclohexene-1-one ring [O4/C1–C3/C14–C16 ring adopts an envelope conformation (Cremer & Pople, 1975) with atom C1 displaced from the C2–C3/C14–C16 mean plane by -0.3155 (17) Å and with the puckering parameters Q = 0.454 (2) Å, θ = 132.1 (4)° and φ = 169.3 (3)°. The methoxy group is slightly deviated from the plane of C17–C22 benzene ring as indicated by the torsion angle C19/C20/O1/C23 = 4.5 (2)°. The methoxyphenyl is almost perpendicularly attached at atom N1, the dihedral angle between the indole and methoxyphenyl rings is 81.78 (8)°. All bond lengths and angles are in normal ranges (Allen et al., 1987).
The crystal packing (Fig. 2) shows that the molecules are linked via weak C10—H10A···O3 [symmetry code; -1 - x, 2 - y, 2 - z] and C18—H18A···O3 [symmetry code; -x, 2 - y, 2 - z] weak interactions to form dimers and these dimers are arranged into chains running approximately along the b axis (Fig. 2). The crystal is stabilized by weak C—H···O intermolecular interactions and C—H···π interactions (Table 1); Cg1 and Cg2 are the centroids of C6–C11 and C17–C22 benzene rings, respectively.