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The title compound, C34H33NO5·0.5H2O, has been synthesized by reacting 3,4,5-trimethoxy­benzaldehyde, 5,5-dimethyl-3-(p-tolyl­amino)cyclo­hex-2-enone and indan-1,3-dione, under microwave irradiation, in a mixture of glycol and acetic acid as solvent. The central N-substituted ring adopts a boat conformation. The uncoordinated water mol­ecule is disordered over two positions, both lying on a twofold symmetry axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806018289/bh2018sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806018289/bh2018Isup2.hkl
Contains datablock I

CCDC reference: 602003

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.006 Å
  • Disorder in main residue
  • R factor = 0.073
  • wR factor = 0.239
  • Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 39 Perc. PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.84 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.49 Ratio PLAT420_ALERT_2_B D-H Without Acceptor >O6 - >H1 ... ?
Alert level C DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 0.676 Test value = 0.600 DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.90 PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.68 e/A   3 PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ... 6179.00 Ang-3 PLAT301_ALERT_3_C Main Residue Disorder ......................... 2.00 Perc. PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C23
0 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 13 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 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

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

7,8-Dihydro-7,7-dimethyl-5-p-tolyl-10-(3,4,5-trimethoxyphenyl)-5H- indeno[1,2-b]quinoline-9,11(6H,10H)-dione hemihydrate top
Crystal data top
C34H33NO5·0.5H2OF(000) = 2312
Mr = 544.62Dx = 1.171 Mg m3
Monoclinic, C2/cMelting point = 471–473 K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 25.094 (6) ÅCell parameters from 1509 reflections
b = 12.755 (3) Åθ = 2.2–20.2°
c = 19.891 (5) ŵ = 0.08 mm1
β = 103.926 (4)°T = 298 K
V = 6179 (3) Å3Block, red
Z = 80.50 × 0.46 × 0.26 mm
Data collection top
Bruker CCD area-detector
diffractometer
5381 independent reflections
Radiation source: fine-focus sealed tube2112 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.097
φ and ω scansθmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2529
Tmin = 0.962, Tmax = 0.980k = 1515
15711 measured reflectionsl = 2321
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)] = 0.073H-atom parameters constrained
wR(F2) = 0.239 w = 1/[σ2(Fo2) + (0.1027P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
5381 reflectionsΔρmax = 0.68 e Å3
378 parametersΔρmin = 0.23 e Å3
180 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0011 (3)
Special details top

Experimental. 1H NMR (DMSO-d6): δ 7.48–7.54 (m, 4H, ArH), 7.27 (d, 1H, ArH, J = 6.8 Hz), 7.18 (t, 1H, ArH, J = 7.4 Hz), 7.01 (t, 1H, ArH, J = 7.6 Hz), 6.59 (s, 2H, ArH), 5.19 (d, 1H, ArH, J = 7.6 Hz), 4.82 (s, 1H, CH), 3.76 (s, 6H, CH3), 3.61 (s, 3H, CH3), 2.50 (s, 3H, CH3), 2.48 (d, 1H, CH2, J = 16.4 Hz), 2.31 (d, 1H, CH2, J = 17.6 Hz), 2.10 (d, 1H, CH2, J = 16.4 Hz), 2.03 (d, 1H, CH2, J = 17.6 Hz), 0.97 (s, 3H, CH3) and 0.93 (s, 3H, CH3)

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*/UeqOcc. (<1)
N10.80371 (13)0.5195 (3)0.35946 (16)0.0425 (9)
O10.61153 (13)0.5437 (3)0.33095 (16)0.0755 (11)
O20.72996 (12)0.7576 (3)0.18020 (15)0.0601 (9)
O30.71910 (19)0.3102 (3)0.08801 (19)0.0872 (12)
O40.61106 (17)0.2947 (3)0.05068 (18)0.0925 (13)
O50.54590 (18)0.4247 (4)0.1004 (2)0.1112 (15)
O61.00000.3007 (10)0.25000.210 (6)0.725 (10)
H11.00870.34110.22040.252*0.725 (10)
O6'1.00000.448 (3)0.25000.210 (6)0.275 (10)
H21.00250.48840.21690.252*0.275 (10)
C10.75220 (17)0.5035 (3)0.3699 (2)0.0411 (11)
C20.73784 (17)0.4512 (3)0.43060 (19)0.0411 (11)
C30.76821 (19)0.4018 (4)0.4890 (2)0.0535 (13)
H30.80610.39510.49680.064*
C40.7399 (2)0.3622 (4)0.5360 (2)0.0585 (13)
H40.75980.32870.57560.070*
C50.6847 (2)0.3704 (4)0.5265 (2)0.0599 (13)
H50.66730.34400.55910.072*
C60.6550 (2)0.4191 (4)0.4670 (2)0.0608 (14)
H60.61700.42400.45880.073*
C70.68140 (17)0.4599 (3)0.4207 (2)0.0445 (11)
C80.65950 (19)0.5183 (4)0.3545 (2)0.0496 (12)
C90.70627 (16)0.5402 (3)0.32543 (19)0.0411 (11)
C100.70595 (15)0.5906 (3)0.25808 (19)0.0412 (11)
H100.68230.65260.25340.049*
C110.76404 (16)0.6276 (3)0.26144 (19)0.0405 (11)
C120.77045 (18)0.7143 (3)0.2165 (2)0.0421 (11)
C130.82681 (16)0.7531 (3)0.2176 (2)0.0463 (12)
H13A0.83520.81170.24950.056*
H13B0.82710.77900.17180.056*
C140.87172 (17)0.6709 (4)0.2387 (2)0.0476 (12)
C150.86603 (16)0.6208 (4)0.3067 (2)0.0491 (12)
H15A0.88960.55960.31590.059*
H15B0.87900.67030.34410.059*
C160.80873 (16)0.5887 (3)0.30684 (19)0.0382 (10)
C170.85150 (16)0.4813 (4)0.4101 (2)0.0474 (12)
C180.87370 (19)0.5419 (4)0.4674 (2)0.0610 (13)
H180.85960.60810.47250.073*
C190.9173 (2)0.5022 (5)0.5170 (2)0.0726 (16)
H190.93250.54300.55560.087*
C200.9386 (2)0.4061 (5)0.5116 (3)0.0705 (15)
C210.91634 (19)0.3479 (4)0.4535 (3)0.0732 (15)
H210.93100.28220.44840.088*
C220.87260 (17)0.3842 (4)0.4021 (2)0.0588 (13)
H220.85800.34370.36310.071*
C230.9854 (2)0.3631 (6)0.5680 (3)0.109 (2)
H23A0.99580.41420.60420.163*
H23B1.01620.34780.54890.163*
H23C0.97360.30010.58660.163*
C240.68206 (17)0.5171 (3)0.1977 (2)0.0423 (11)
C250.71465 (19)0.4507 (4)0.1701 (2)0.0502 (12)
H250.75270.45370.18570.060*
C260.6907 (2)0.3792 (4)0.1188 (2)0.0577 (13)
C270.6344 (2)0.3732 (4)0.0966 (2)0.0666 (15)
C280.6018 (2)0.4398 (5)0.1250 (3)0.0708 (16)
C290.62586 (18)0.5123 (4)0.1736 (2)0.0580 (13)
H290.60390.55920.19050.070*
C300.7762 (3)0.3193 (5)0.1032 (4)0.109 (2)
H30A0.79090.26720.07780.164*
H30B0.79100.30910.15190.164*
H30C0.78600.38780.09020.164*
C310.6057 (18)0.3174 (16)0.0213 (10)0.087 (6)0.56 (6)
H31A0.58940.25840.04870.130*0.56 (6)
H31B0.64130.33110.02930.130*0.56 (6)
H31C0.58270.37780.03410.130*0.56 (6)
C31'0.5779 (19)0.333 (3)0.0163 (14)0.087 (7)0.44 (6)
H31D0.56320.27490.04520.131*0.44 (6)
H31E0.60070.37460.03860.131*0.44 (6)
H31F0.54840.37590.00860.131*0.44 (6)
C320.5112 (3)0.4824 (7)0.1355 (4)0.146 (3)
H32A0.47340.46680.11460.220*
H32B0.51750.55620.13180.220*
H32C0.51970.46260.18350.220*
C330.86638 (19)0.5878 (4)0.1818 (2)0.0673 (15)
H33A0.83100.55490.17400.101*
H33B0.89460.53590.19590.101*
H33C0.87020.62060.13970.101*
C340.92793 (18)0.7216 (4)0.2511 (3)0.0712 (15)
H34A0.93160.77350.28690.107*
H34B0.93200.75450.20920.107*
H34C0.95580.66910.26500.107*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.030 (2)0.056 (2)0.0381 (19)0.0003 (17)0.0034 (16)0.0114 (18)
O10.035 (2)0.120 (3)0.073 (2)0.0171 (19)0.0162 (16)0.019 (2)
O20.054 (2)0.071 (2)0.0538 (19)0.0135 (17)0.0104 (16)0.0178 (17)
O30.110 (3)0.074 (3)0.086 (3)0.007 (2)0.038 (2)0.024 (2)
O40.126 (3)0.075 (3)0.058 (2)0.034 (2)0.016 (2)0.001 (2)
O50.063 (3)0.138 (4)0.109 (3)0.022 (3)0.026 (2)0.016 (3)
O60.187 (11)0.159 (10)0.256 (13)0.0000.001 (10)0.000
O6'0.187 (11)0.159 (10)0.256 (13)0.0000.001 (10)0.000
C10.040 (3)0.043 (3)0.039 (2)0.002 (2)0.007 (2)0.003 (2)
C20.050 (3)0.043 (3)0.032 (2)0.007 (2)0.012 (2)0.003 (2)
C30.051 (3)0.063 (3)0.046 (3)0.006 (2)0.010 (2)0.007 (2)
C40.071 (4)0.063 (4)0.042 (3)0.006 (3)0.015 (3)0.001 (2)
C50.074 (4)0.063 (4)0.049 (3)0.009 (3)0.028 (3)0.000 (3)
C60.054 (3)0.076 (4)0.058 (3)0.000 (3)0.026 (3)0.004 (3)
C70.040 (3)0.054 (3)0.041 (3)0.001 (2)0.014 (2)0.006 (2)
C80.039 (3)0.062 (3)0.047 (3)0.004 (2)0.011 (2)0.006 (2)
C90.033 (2)0.053 (3)0.037 (2)0.005 (2)0.009 (2)0.002 (2)
C100.030 (2)0.049 (3)0.043 (2)0.008 (2)0.0059 (19)0.004 (2)
C110.036 (3)0.048 (3)0.037 (2)0.003 (2)0.0078 (19)0.002 (2)
C120.047 (3)0.043 (3)0.036 (2)0.006 (2)0.010 (2)0.001 (2)
C130.048 (3)0.049 (3)0.043 (2)0.001 (2)0.014 (2)0.007 (2)
C140.042 (3)0.059 (3)0.043 (3)0.007 (2)0.014 (2)0.002 (2)
C150.036 (3)0.062 (3)0.049 (3)0.002 (2)0.009 (2)0.008 (2)
C160.037 (3)0.044 (3)0.033 (2)0.001 (2)0.0084 (19)0.003 (2)
C170.031 (2)0.062 (3)0.046 (3)0.003 (2)0.003 (2)0.015 (2)
C180.054 (3)0.072 (3)0.049 (3)0.008 (3)0.004 (2)0.006 (3)
C190.061 (3)0.093 (4)0.053 (3)0.014 (3)0.007 (3)0.011 (3)
C200.041 (3)0.095 (4)0.070 (3)0.002 (3)0.001 (3)0.034 (3)
C210.046 (3)0.079 (4)0.092 (4)0.015 (3)0.010 (3)0.033 (3)
C220.038 (3)0.063 (3)0.070 (3)0.005 (2)0.002 (2)0.013 (3)
C230.059 (4)0.160 (6)0.096 (4)0.005 (4)0.005 (3)0.063 (4)
C240.036 (3)0.050 (3)0.040 (2)0.002 (2)0.008 (2)0.006 (2)
C250.047 (3)0.057 (3)0.045 (3)0.006 (3)0.008 (2)0.009 (2)
C260.071 (4)0.055 (3)0.048 (3)0.004 (3)0.018 (3)0.002 (3)
C270.078 (4)0.064 (4)0.046 (3)0.024 (3)0.006 (3)0.001 (3)
C280.047 (3)0.085 (4)0.067 (3)0.011 (3)0.015 (3)0.007 (3)
C290.036 (3)0.073 (4)0.057 (3)0.001 (2)0.004 (2)0.003 (3)
C300.119 (6)0.083 (5)0.145 (6)0.004 (4)0.069 (5)0.025 (4)
C310.111 (14)0.078 (9)0.057 (7)0.005 (10)0.009 (10)0.006 (6)
C31'0.086 (15)0.106 (13)0.059 (9)0.009 (12)0.005 (11)0.021 (9)
C320.057 (5)0.157 (8)0.202 (8)0.015 (5)0.014 (5)0.027 (7)
C330.064 (3)0.079 (4)0.063 (3)0.008 (3)0.024 (3)0.006 (3)
C340.046 (3)0.096 (4)0.074 (3)0.015 (3)0.019 (3)0.010 (3)
Geometric parameters (Å, º) top
N1—C11.373 (5)C15—H15A0.9700
N1—C161.398 (5)C15—H15B0.9700
N1—C171.452 (5)C17—C221.371 (6)
O1—C81.225 (5)C17—C181.378 (6)
O2—C121.227 (4)C18—C191.381 (6)
O3—C261.367 (6)C18—H180.9300
O3—C301.396 (7)C19—C201.353 (7)
O4—C271.387 (5)C19—H190.9300
O4—C311.43 (2)C20—C211.374 (7)
O4—C31'1.47 (3)C20—C231.517 (6)
O5—C281.383 (6)C21—C221.387 (6)
O5—C321.442 (8)C21—H210.9300
O6—H10.8500C22—H220.9300
O6'—H20.8500C23—H23A0.9600
C1—C91.356 (5)C23—H23B0.9600
C1—C21.497 (5)C23—H23C0.9600
C2—C31.378 (5)C24—C291.377 (5)
C2—C71.387 (6)C24—C251.380 (6)
C3—C41.398 (6)C25—C261.392 (6)
C3—H30.9300C25—H250.9300
C4—C51.355 (6)C26—C271.377 (7)
C4—H40.9300C27—C281.390 (7)
C5—C61.384 (6)C28—C291.369 (7)
C5—H50.9300C29—H290.9300
C6—C71.361 (6)C30—H30A0.9600
C6—H60.9300C30—H30B0.9600
C7—C81.498 (6)C30—H30C0.9600
C8—C91.454 (6)C31—H31A0.9600
C9—C101.484 (5)C31—H31B0.9600
C10—C111.518 (5)C31—H31C0.9600
C10—C241.528 (6)C31'—H31D0.9600
C10—H100.9800C31'—H31E0.9600
C11—C161.354 (5)C31'—H31F0.9600
C11—C121.455 (6)C32—H32A0.9600
C12—C131.494 (6)C32—H32B0.9600
C13—C141.523 (6)C32—H32C0.9600
C13—H13A0.9700C33—H33A0.9600
C13—H13B0.9700C33—H33B0.9600
C14—C341.517 (6)C33—H33C0.9600
C14—C151.533 (6)C34—H34A0.9600
C14—C331.534 (6)C34—H34B0.9600
C15—C161.496 (5)C34—H34C0.9600
C1—N1—C16117.7 (3)C20—C19—C18122.3 (5)
C1—N1—C17119.7 (3)C20—C19—H19118.8
C16—N1—C17121.5 (3)C18—C19—H19118.8
C26—O3—C30118.0 (4)C19—C20—C21118.0 (5)
C27—O4—C31115.8 (9)C19—C20—C23121.2 (6)
C27—O4—C31'114.2 (12)C21—C20—C23120.8 (6)
C28—O5—C32115.8 (5)C20—C21—C22121.9 (5)
C9—C1—N1122.2 (4)C20—C21—H21119.1
C9—C1—C2110.4 (4)C22—C21—H21119.1
N1—C1—C2127.3 (3)C17—C22—C21118.4 (5)
C3—C2—C7119.7 (4)C17—C22—H22120.8
C3—C2—C1133.7 (4)C21—C22—H22120.8
C7—C2—C1106.6 (3)C20—C23—H23A109.5
C2—C3—C4117.5 (4)C20—C23—H23B109.5
C2—C3—H3121.3H23A—C23—H23B109.5
C4—C3—H3121.3C20—C23—H23C109.5
C5—C4—C3123.0 (4)H23A—C23—H23C109.5
C5—C4—H4118.5H23B—C23—H23C109.5
C3—C4—H4118.5C29—C24—C25119.3 (4)
C4—C5—C6118.4 (4)C29—C24—C10118.4 (4)
C4—C5—H5120.8C25—C24—C10122.1 (4)
C6—C5—H5120.8C24—C25—C26120.0 (4)
C7—C6—C5120.0 (5)C24—C25—H25120.0
C7—C6—H6120.0C26—C25—H25120.0
C5—C6—H6120.0O3—C26—C27115.2 (5)
C6—C7—C2121.3 (4)O3—C26—C25124.7 (5)
C6—C7—C8130.6 (4)C27—C26—C25120.0 (5)
C2—C7—C8108.1 (4)C26—C27—O4119.3 (6)
O1—C8—C9127.6 (4)C26—C27—C28119.6 (5)
O1—C8—C7125.9 (4)O4—C27—C28120.8 (5)
C9—C8—C7106.5 (4)C29—C28—O5125.6 (6)
C1—C9—C8108.4 (4)C29—C28—C27119.8 (5)
C1—C9—C10123.9 (4)O5—C28—C27114.6 (5)
C8—C9—C10127.7 (4)C28—C29—C24121.1 (5)
C9—C10—C11107.4 (3)C28—C29—H29119.4
C9—C10—C24111.1 (3)C24—C29—H29119.4
C11—C10—C24114.6 (3)O3—C30—H30A109.5
C9—C10—H10107.9O3—C30—H30B109.5
C11—C10—H10107.9H30A—C30—H30B109.5
C24—C10—H10107.9O3—C30—H30C109.5
C16—C11—C12119.5 (4)H30A—C30—H30C109.5
C16—C11—C10123.2 (4)H30B—C30—H30C109.5
C12—C11—C10117.2 (3)O4—C31—H31A109.5
O2—C12—C11120.3 (4)O4—C31—H31B109.5
O2—C12—C13120.4 (4)H31A—C31—H31B109.5
C11—C12—C13119.2 (4)O4—C31—H31C109.5
C12—C13—C14114.3 (4)H31A—C31—H31C109.5
C12—C13—H13A108.7H31B—C31—H31C109.5
C14—C13—H13A108.7O4—C31'—H31D109.5
C12—C13—H13B108.7O4—C31'—H31E109.5
C14—C13—H13B108.7H31D—C31'—H31E109.5
H13A—C13—H13B107.6O4—C31'—H31F109.5
C34—C14—C13110.4 (4)H31D—C31'—H31F109.5
C34—C14—C15108.3 (3)H31E—C31'—H31F109.5
C13—C14—C15108.1 (3)O5—C32—H32A109.5
C34—C14—C33109.1 (4)O5—C32—H32B109.5
C13—C14—C33110.2 (3)H32A—C32—H32B109.5
C15—C14—C33110.7 (4)O5—C32—H32C109.5
C16—C15—C14114.2 (3)H32A—C32—H32C109.5
C16—C15—H15A108.7H32B—C32—H32C109.5
C14—C15—H15A108.7C14—C33—H33A109.5
C16—C15—H15B108.7C14—C33—H33B109.5
C14—C15—H15B108.7H33A—C33—H33B109.5
H15A—C15—H15B107.6C14—C33—H33C109.5
C11—C16—N1121.5 (4)H33A—C33—H33C109.5
C11—C16—C15122.7 (4)H33B—C33—H33C109.5
N1—C16—C15115.7 (3)C14—C34—H34A109.5
C22—C17—C18120.8 (4)C14—C34—H34B109.5
C22—C17—N1120.0 (4)H34A—C34—H34B109.5
C18—C17—N1119.2 (4)C14—C34—H34C109.5
C17—C18—C19118.6 (5)H34A—C34—H34C109.5
C17—C18—H18120.7H34B—C34—H34C109.5
C19—C18—H18120.7
 

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