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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1652.
Published online 2008 July 31. doi:  10.1107/S1600536808023866
PMCID: PMC2962249

3-[4-(Dimethylamino)phenyl]-1,5-di­phenylpentane-1,5-dione

Abstract

The asymmetric unit of the title compound, C25H25NO2, contains two independent mol­ecules. The crystal packing exhibits weak inter­molecular C—H(...)O, C—H(...)π and π–π inter­actions.

Related literature

For crystal structures of related compounds, see Das et al. (1994 [triangle]); Huang et al. (2006 [triangle]). For general background, see Bose et al. (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1652-scheme1.jpg

Experimental

Crystal data

  • C25H25NO2
  • M r = 371.46
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1652-efi1.jpg
  • a = 9.926 (1) Å
  • b = 11.3749 (14) Å
  • c = 18.853 (2) Å
  • α = 90.443 (10)°
  • β = 94.782 (10)°
  • γ = 99.862 (2)°
  • V = 2089.3 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 298 (2) K
  • 0.49 × 0.40 × 0.29 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.965, T max = 0.979
  • 11011 measured reflections
  • 7259 independent reflections
  • 3113 reflections with I > 2σ(I)
  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.052
  • wR(F 2) = 0.139
  • S = 0.99
  • 7259 reflections
  • 505 parameters
  • H-atom parameters constrained
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.15 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Centroid(...)centroid distance (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808023866/cv2435sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023866/cv2435Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors acknowledge the financial support of the Natural Science Foundation of Liaocheng University (grant No. X071013).

supplementary crystallographic information

Comment

The "Grindstone Chemistry" method for conducting exothermic reactions in the solvent-free mode has been recently published (Bose et al., 2004). When this protocol was applied to the Pechmann synthesis on a multi-molar scale, the expected coumarins were obtained in a few minutes as pure products in high yield by solvent-free grinding. Since this reaction proved to be exothermic, we tested energy-saving procedures developed in our laboratory for the preparation of 1,5-diketones starting from the fragrant aldehydes and fragrant ketones in the presence of NaOH under solvent-free conditions. Using this method, we obtained the title compound, (I). Herewith we present its crystal structure.

In (I), all bond lengths and angles are normal and correspond to those observed in 1,3,5-triphenyl-pentane-1,5-diketone (Das et al., 1994) and 1,5-diphenyl-3-(2-pyridyl)pentane-1,5-dione (Huang et al.cv2222435, 2006). The asymmetric unit of (I) contains two independent molecules (Fig. 1) with different conformations - the dihedral angles formed by two phenyl rings in each molecule are 85.48 (7) and 71.26 (7)°, respectively.

The weak intermolecular π–π (Table 1) and C—H···π (Table 2) interactions, and C—H···O hydrogen bonds (Table 2) contribute to the crystal packing stabilization.

Experimental

Acetophenone (6.25 mmol) and 4-(dimethylamino)benzaldehyde (3.125 mmol), NaOH (6.25 mmol) were aggregated with glass paddle in an open flask. The resulting mixture was washed with water for several times for removing NaOH, and recrystalized from ethanol, and afforded the title compound as a crystalline solid. Elemental analysis: calculated for C25 H25 NO2: C 80.83, H 6.78, N 3.77%; Found: C80.88, H 6.83, N3.65%.

Refinement

All H atoms were positioned geometrically (C—H 0.93–0.98 Å) and refined using a riding model, with Uiso(H) = 1.2-1.5Ueq(C).

Figures

Fig. 1.
Two independent molecules of (I) with the atom numbering scheme and 30% probability displacement ellipsoids. Hydrogen atoms are omitted for clarity

Crystal data

C25H25NO2Z = 4
Mr = 371.46F000 = 792
Triclinic, P1Dx = 1.181 Mg m3
a = 9.9260 (10) ÅMo Kα radiation λ = 0.71073 Å
b = 11.3749 (14) ÅCell parameters from 1876 reflections
c = 18.853 (2) Åθ = 2.3–21.9º
α = 90.4430 (10)ºµ = 0.07 mm1
β = 94.7820 (10)ºT = 298 (2) K
γ = 99.862 (2)ºNeedle, orange
V = 2089.3 (4) Å30.49 × 0.40 × 0.29 mm

Data collection

Bruker SMART CCD area-detector diffractometer7259 independent reflections
Radiation source: fine-focus sealed tube3113 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.032
T = 298(2) Kθmax = 25.0º
phi and ω scansθmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −11→11
Tmin = 0.965, Tmax = 0.979k = −13→11
11011 measured reflectionsl = −21→22

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.139  w = 1/[σ2(Fo2) + (0.0484P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max = 0.001
7259 reflectionsΔρmax = 0.17 e Å3
505 parametersΔρmin = −0.15 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

xyzUiso*/Ueq
N1−0.2518 (3)0.1016 (2)0.07384 (14)0.0746 (8)
N20.7107 (3)0.3289 (3)0.54492 (15)0.0770 (8)
O10.3269 (2)0.29812 (16)0.24964 (10)0.0591 (6)
O20.3520 (2)0.69008 (17)0.22151 (11)0.0672 (6)
O30.9223 (2)0.7410 (2)0.31919 (13)0.0890 (8)
O40.7803 (2)0.5520 (2)0.12546 (11)0.0851 (8)
C10.1699 (3)0.4704 (2)0.20068 (15)0.0484 (8)
H10.25180.46980.17510.058*
C20.0584 (3)0.3716 (2)0.16849 (15)0.0442 (7)
C3−0.0406 (3)0.3083 (2)0.20687 (15)0.0538 (8)
H3−0.03840.32470.25540.065*
C4−0.1433 (3)0.2212 (2)0.17590 (15)0.0548 (8)
H4−0.20840.18110.20390.066*
C5−0.1514 (3)0.1923 (2)0.10427 (15)0.0504 (8)
C6−0.0526 (3)0.2565 (3)0.06505 (15)0.0638 (9)
H6−0.05490.24080.01640.077*
C70.0484 (3)0.3429 (3)0.09681 (15)0.0586 (9)
H70.11290.38390.06880.070*
C8−0.2579 (4)0.0717 (3)0.00048 (18)0.1051 (14)
H8A−0.27230.1397−0.02710.158*
H8B−0.33220.0068−0.01120.158*
H8C−0.17310.0483−0.01000.158*
C9−0.3612 (3)0.0485 (3)0.11383 (19)0.0898 (12)
H9A−0.32610.00170.15090.135*
H9B−0.4293−0.00200.08300.135*
H9C−0.40180.10990.13450.135*
C100.2091 (3)0.4528 (2)0.27920 (14)0.0517 (8)
H10A0.27780.52000.29690.062*
H10B0.12880.45240.30530.062*
C110.2644 (3)0.3393 (2)0.29382 (15)0.0438 (7)
C120.2454 (3)0.2790 (3)0.36266 (14)0.0455 (7)
C130.2109 (3)0.3365 (3)0.42188 (16)0.0600 (9)
H130.19700.41520.41880.072*
C140.1968 (3)0.2784 (4)0.48502 (18)0.0782 (11)
H140.17610.31800.52500.094*
C150.2138 (4)0.1613 (4)0.48865 (19)0.0938 (13)
H150.20280.12110.53110.113*
C160.2465 (4)0.1033 (3)0.4305 (2)0.0950 (13)
H160.25740.02380.43340.114*
C170.2635 (3)0.1622 (3)0.36776 (17)0.0728 (10)
H170.28730.12290.32850.087*
C180.1245 (3)0.5911 (2)0.18845 (16)0.0560 (8)
H18A0.08510.59220.13970.067*
H18B0.05240.59760.21920.067*
C190.2346 (3)0.6992 (2)0.20144 (15)0.0475 (8)
C200.1967 (3)0.8179 (2)0.18730 (14)0.0469 (7)
C210.2981 (3)0.9170 (3)0.19303 (14)0.0594 (9)
H210.38840.90770.20490.071*
C220.2693 (4)1.0295 (3)0.18159 (17)0.0695 (10)
H220.33981.09520.18510.083*
C230.1376 (5)1.0446 (3)0.16508 (18)0.0801 (11)
H230.11751.12090.15840.096*
C240.0341 (4)0.9469 (3)0.15827 (19)0.0836 (11)
H24−0.05600.95700.14640.100*
C250.0640 (3)0.8339 (3)0.16907 (17)0.0682 (9)
H25−0.00620.76800.16400.082*
C260.7350 (3)0.5403 (3)0.26971 (15)0.0563 (8)
H260.82980.54660.25720.068*
C270.7282 (3)0.4872 (2)0.34239 (16)0.0505 (8)
C280.8433 (3)0.4613 (2)0.38126 (17)0.0553 (8)
H280.92780.48060.36240.066*
C290.8387 (3)0.4083 (3)0.44654 (17)0.0580 (9)
H290.91930.39210.47010.070*
C300.7166 (3)0.3785 (3)0.47788 (17)0.0551 (8)
C310.6001 (3)0.4050 (3)0.43978 (17)0.0716 (10)
H310.51550.38650.45860.086*
C320.6080 (3)0.4582 (3)0.37451 (17)0.0678 (10)
H320.52780.47530.35090.081*
C330.8266 (4)0.2791 (3)0.57485 (19)0.0954 (12)
H33A0.84110.21500.54460.143*
H33B0.80890.24940.62130.143*
H33C0.90710.33990.57860.143*
C340.5808 (4)0.2732 (4)0.5674 (2)0.1185 (16)
H34A0.51910.32970.56570.178*
H34B0.59340.24630.61530.178*
H34C0.54300.20620.53640.178*
C350.6987 (3)0.6660 (3)0.26728 (16)0.0640 (9)
H35A0.68140.68650.21790.077*
H35B0.61450.66510.29000.077*
C360.8079 (3)0.7616 (3)0.30282 (15)0.0579 (9)
C370.7755 (4)0.8824 (3)0.31653 (14)0.0547 (8)
C380.8810 (4)0.9747 (3)0.33986 (16)0.0742 (10)
H380.97100.96100.34420.089*
C390.8547 (5)1.0854 (3)0.35654 (18)0.0856 (12)
H390.92651.14580.37240.103*
C400.7232 (5)1.1073 (3)0.34998 (19)0.0929 (13)
H400.70551.18240.36190.111*
C410.6170 (4)1.0184 (4)0.32569 (19)0.0912 (12)
H410.52741.03320.32060.109*
C420.6445 (4)0.9068 (3)0.30883 (16)0.0691 (10)
H420.57260.84700.29190.083*
C430.6433 (3)0.4592 (3)0.21342 (14)0.0594 (9)
H43A0.64640.37680.22510.071*
H43B0.54940.47150.21560.071*
C440.6818 (3)0.4790 (3)0.13862 (16)0.0596 (9)
C450.5958 (4)0.4051 (3)0.07981 (15)0.0560 (8)
C460.4716 (4)0.3347 (3)0.09015 (16)0.0652 (9)
H460.44070.32930.13540.078*
C470.3927 (4)0.2721 (3)0.0337 (2)0.0849 (12)
H470.30920.22470.04110.102*
C480.4374 (5)0.2799 (3)−0.0329 (2)0.0950 (14)
H480.38360.2386−0.07090.114*
C490.5601 (5)0.3476 (4)−0.0439 (2)0.0997 (14)
H490.59020.3514−0.08930.120*
C500.6408 (4)0.4110 (3)0.01199 (19)0.0811 (11)
H500.72470.45720.00410.097*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.076 (2)0.073 (2)0.0634 (19)−0.0123 (17)−0.0067 (16)−0.0099 (15)
N20.069 (2)0.091 (2)0.068 (2)0.0095 (18)−0.0050 (17)0.0116 (17)
O10.0684 (15)0.0540 (13)0.0604 (13)0.0197 (11)0.0191 (11)0.0048 (10)
O20.0488 (14)0.0509 (13)0.0990 (17)0.0065 (11)−0.0074 (13)0.0100 (11)
O30.0569 (16)0.0780 (17)0.124 (2)0.0050 (13)−0.0276 (15)0.0143 (14)
O40.0693 (17)0.0997 (19)0.0812 (16)−0.0029 (14)0.0096 (13)0.0295 (14)
C10.0450 (19)0.0388 (18)0.061 (2)0.0068 (15)0.0029 (15)0.0055 (14)
C20.0478 (19)0.0331 (17)0.0509 (19)0.0072 (14)−0.0012 (15)0.0051 (14)
C30.061 (2)0.0469 (19)0.0516 (18)0.0044 (17)0.0039 (17)−0.0019 (15)
C40.052 (2)0.053 (2)0.056 (2)−0.0037 (16)0.0100 (16)0.0003 (16)
C50.051 (2)0.0440 (19)0.054 (2)0.0041 (16)−0.0040 (16)−0.0008 (16)
C60.079 (3)0.061 (2)0.0468 (19)0.001 (2)0.0007 (18)−0.0006 (17)
C70.069 (2)0.051 (2)0.053 (2)−0.0005 (18)0.0084 (17)0.0082 (16)
C80.129 (4)0.096 (3)0.072 (3)−0.021 (3)−0.012 (2)−0.021 (2)
C90.070 (3)0.075 (3)0.113 (3)−0.015 (2)0.000 (2)−0.015 (2)
C100.053 (2)0.0395 (18)0.062 (2)0.0083 (15)0.0004 (16)−0.0042 (15)
C110.0385 (18)0.0359 (18)0.0550 (19)0.0024 (14)0.0009 (15)−0.0048 (15)
C120.0433 (19)0.0454 (19)0.0472 (19)0.0081 (15)−0.0004 (15)0.0015 (15)
C130.060 (2)0.068 (2)0.054 (2)0.0176 (18)0.0000 (17)−0.0043 (18)
C140.082 (3)0.105 (3)0.050 (2)0.020 (2)0.0064 (19)−0.004 (2)
C150.118 (4)0.106 (4)0.053 (2)0.007 (3)0.007 (2)0.021 (2)
C160.143 (4)0.067 (3)0.074 (3)0.018 (2)0.002 (3)0.021 (2)
C170.105 (3)0.055 (2)0.062 (2)0.023 (2)0.007 (2)0.0072 (18)
C180.046 (2)0.0402 (18)0.079 (2)0.0042 (15)−0.0013 (17)0.0052 (15)
C190.045 (2)0.0433 (19)0.0547 (19)0.0074 (16)0.0055 (16)0.0053 (14)
C200.050 (2)0.0403 (19)0.0510 (18)0.0101 (16)0.0035 (16)0.0072 (14)
C210.065 (2)0.045 (2)0.065 (2)0.0048 (18)−0.0004 (17)0.0017 (16)
C220.087 (3)0.043 (2)0.076 (2)0.007 (2)0.005 (2)0.0001 (17)
C230.106 (3)0.047 (2)0.095 (3)0.028 (2)0.020 (3)0.0124 (19)
C240.068 (3)0.068 (3)0.124 (3)0.033 (2)0.015 (2)0.022 (2)
C250.063 (2)0.047 (2)0.096 (3)0.0117 (18)0.009 (2)0.0137 (18)
C260.044 (2)0.060 (2)0.064 (2)0.0085 (16)0.0022 (16)0.0021 (17)
C270.0353 (19)0.056 (2)0.059 (2)0.0082 (15)0.0001 (16)−0.0059 (16)
C280.038 (2)0.058 (2)0.070 (2)0.0100 (16)0.0025 (17)−0.0009 (17)
C290.043 (2)0.060 (2)0.070 (2)0.0120 (17)−0.0063 (18)−0.0004 (18)
C300.049 (2)0.059 (2)0.055 (2)0.0056 (17)−0.0039 (18)−0.0038 (16)
C310.044 (2)0.106 (3)0.062 (2)0.0048 (19)0.0057 (18)0.005 (2)
C320.040 (2)0.100 (3)0.063 (2)0.0158 (19)−0.0046 (18)0.004 (2)
C330.089 (3)0.105 (3)0.089 (3)0.016 (2)−0.009 (2)0.035 (2)
C340.090 (3)0.163 (4)0.101 (3)0.006 (3)0.022 (3)0.051 (3)
C350.053 (2)0.064 (2)0.071 (2)0.0066 (18)−0.0096 (17)0.0012 (17)
C360.049 (2)0.066 (2)0.0541 (19)0.0009 (19)−0.0065 (17)0.0113 (17)
C370.061 (2)0.054 (2)0.0440 (18)−0.0014 (19)−0.0017 (17)0.0060 (15)
C380.074 (3)0.072 (3)0.067 (2)−0.010 (2)−0.0039 (19)0.0096 (19)
C390.106 (4)0.064 (3)0.076 (3)−0.011 (3)−0.005 (3)−0.001 (2)
C400.122 (4)0.070 (3)0.083 (3)0.008 (3)0.005 (3)−0.013 (2)
C410.091 (3)0.080 (3)0.104 (3)0.022 (3)0.007 (2)−0.018 (2)
C420.067 (3)0.068 (3)0.069 (2)0.006 (2)0.000 (2)−0.0034 (18)
C430.059 (2)0.064 (2)0.055 (2)0.0085 (17)0.0050 (17)0.0033 (16)
C440.058 (2)0.058 (2)0.066 (2)0.0190 (18)0.0085 (19)0.0140 (18)
C450.074 (2)0.053 (2)0.049 (2)0.0256 (18)0.0162 (18)0.0104 (16)
C460.086 (3)0.055 (2)0.054 (2)0.0110 (19)0.0068 (19)0.0005 (17)
C470.114 (3)0.063 (2)0.072 (3)0.008 (2)−0.007 (2)−0.007 (2)
C480.162 (5)0.066 (3)0.058 (3)0.031 (3)−0.009 (3)−0.005 (2)
C490.162 (5)0.096 (3)0.052 (3)0.047 (3)0.020 (3)0.001 (2)
C500.103 (3)0.082 (3)0.068 (3)0.033 (2)0.028 (2)0.019 (2)

Geometric parameters (Å, °)

N1—C51.389 (3)C23—C241.376 (4)
N1—C81.416 (4)C23—H230.9300
N1—C91.425 (4)C24—C251.381 (4)
N2—C301.390 (4)C24—H240.9300
N2—C341.435 (4)C25—H250.9300
N2—C331.443 (4)C26—C271.503 (4)
O1—C111.216 (3)C26—C431.530 (3)
O2—C191.217 (3)C26—C351.534 (4)
O3—C361.214 (3)C26—H260.9800
O4—C441.213 (3)C27—C321.374 (4)
C1—C21.519 (3)C27—C281.382 (4)
C1—C101.523 (3)C28—C291.376 (4)
C1—C181.529 (4)C28—H280.9300
C1—H10.9800C29—C301.383 (4)
C2—C31.376 (3)C29—H290.9300
C2—C71.379 (3)C30—C311.389 (4)
C3—C41.381 (3)C31—C321.378 (4)
C3—H30.9301C31—H310.9300
C4—C51.380 (4)C32—H320.9300
C4—H40.9300C33—H33A0.9600
C5—C61.388 (4)C33—H33B0.9600
C6—C71.372 (3)C33—H33C0.9600
C6—H60.9301C34—H34A0.9600
C7—H70.9300C34—H34B0.9600
C8—H8A0.9600C34—H34C0.9600
C8—H8B0.9600C35—C361.506 (4)
C8—H8C0.9600C35—H35A0.9700
C9—H9A0.9600C35—H35B0.9700
C9—H9B0.9600C36—C371.489 (4)
C9—H9C0.9600C37—C421.371 (4)
C10—C111.506 (4)C37—C381.390 (4)
C10—H10A0.9700C38—C391.368 (4)
C10—H10B0.9700C38—H380.9300
C11—O11.216 (3)C39—C401.366 (5)
C11—C121.484 (4)C39—H390.9300
C12—C171.374 (4)C40—C411.375 (4)
C12—C131.386 (4)C40—H400.9300
C13—C141.371 (4)C41—C421.384 (4)
C13—H130.9300C41—H410.9300
C14—C151.372 (5)C42—H420.9300
C14—H140.9300C43—C441.500 (4)
C15—C161.366 (5)C43—H43A0.9700
C15—H150.9300C43—H43B0.9700
C16—C171.372 (4)C44—C451.499 (4)
C16—H160.9300C45—C461.380 (4)
C17—H170.9300C45—C501.387 (4)
C18—C191.503 (3)C46—C471.382 (4)
C18—H18A0.9700C46—H460.9299
C18—H18B0.9700C47—C481.364 (5)
C19—C201.483 (4)C47—H470.9300
C20—C211.374 (3)C48—C491.357 (5)
C20—C251.376 (4)C48—H480.9299
C21—C221.373 (4)C49—C501.386 (5)
C21—H210.9300C49—H490.9298
C22—C231.359 (4)C50—H500.9300
C22—H220.9300
Cg1···Cg1i3.773 (4)
C5—N1—C8120.7 (3)C20—C25—C24120.6 (3)
C5—N1—C9120.1 (3)C20—C25—H25119.7
C8—N1—C9118.7 (3)C24—C25—H25119.7
C30—N2—C34119.6 (3)C27—C26—C43111.4 (2)
C30—N2—C33118.6 (3)C27—C26—C35112.9 (2)
C34—N2—C33114.6 (3)C43—C26—C35109.9 (2)
C2—C1—C10112.8 (2)C27—C26—H26107.5
C2—C1—C18109.4 (2)C43—C26—H26107.5
C10—C1—C18111.5 (2)C35—C26—H26107.5
C2—C1—H1107.6C32—C27—C28114.9 (3)
C10—C1—H1107.6C32—C27—C26123.1 (3)
C18—C1—H1107.6C28—C27—C26122.0 (3)
C3—C2—C7115.7 (3)C29—C28—C27123.0 (3)
C3—C2—C1123.5 (3)C29—C28—H28118.5
C7—C2—C1120.8 (3)C27—C28—H28118.5
C2—C3—C4122.3 (3)C28—C29—C30121.4 (3)
C2—C3—H3118.8C28—C29—H29119.3
C4—C3—H3118.8C30—C29—H29119.3
C5—C4—C3121.5 (3)C29—C30—C31116.3 (3)
C5—C4—H4119.3C29—C30—N2122.2 (3)
C3—C4—H4119.3C31—C30—N2121.4 (3)
C4—C5—C6116.5 (3)C32—C31—C30120.9 (3)
C4—C5—N1121.3 (3)C32—C31—H31119.5
C6—C5—N1122.2 (3)C30—C31—H31119.5
C7—C6—C5121.1 (3)C27—C32—C31123.5 (3)
C7—C6—H6119.5C27—C32—H32118.3
C5—C6—H6119.5C31—C32—H32118.3
C6—C7—C2122.9 (3)N2—C33—H33A109.5
C6—C7—H7118.6N2—C33—H33B109.5
C2—C7—H7118.6H33A—C33—H33B109.5
N1—C8—H8A109.5N2—C33—H33C109.5
N1—C8—H8B109.5H33A—C33—H33C109.5
H8A—C8—H8B109.5H33B—C33—H33C109.5
N1—C8—H8C109.5N2—C34—H34A109.5
H8A—C8—H8C109.5N2—C34—H34B109.5
H8B—C8—H8C109.5H34A—C34—H34B109.5
N1—C9—H9A109.5N2—C34—H34C109.5
N1—C9—H9B109.5H34A—C34—H34C109.5
H9A—C9—H9B109.5H34B—C34—H34C109.5
N1—C9—H9C109.5C36—C35—C26114.4 (3)
H9A—C9—H9C109.5C36—C35—H35A108.7
H9B—C9—H9C109.5C26—C35—H35A108.7
C11—C10—C1113.8 (2)C36—C35—H35B108.7
C11—C10—H10A108.8C26—C35—H35B108.7
C1—C10—H10A108.8H35A—C35—H35B107.6
C11—C10—H10B108.8O3—C36—C37120.1 (3)
C1—C10—H10B108.8O3—C36—C35120.3 (3)
H10A—C10—H10B107.7C37—C36—C35119.6 (3)
O1—C11—C12119.9 (3)C42—C37—C38117.8 (3)
O1—C11—C12119.9 (3)C42—C37—C36122.9 (3)
O1—C11—C10120.0 (3)C38—C37—C36119.3 (3)
O1—C11—C10120.0 (3)C39—C38—C37121.1 (4)
C12—C11—C10120.2 (3)C39—C38—H38119.4
C17—C12—C13119.0 (3)C37—C38—H38119.4
C17—C12—C11118.6 (3)C40—C39—C38120.2 (4)
C13—C12—C11122.3 (3)C40—C39—H39119.9
C14—C13—C12120.6 (3)C38—C39—H39119.9
C14—C13—H13119.7C39—C40—C41119.9 (4)
C12—C13—H13119.7C39—C40—H40120.0
C13—C14—C15119.3 (3)C41—C40—H40120.0
C13—C14—H14120.3C40—C41—C42119.5 (4)
C15—C14—H14120.3C40—C41—H41120.3
C16—C15—C14120.6 (4)C42—C41—H41120.3
C16—C15—H15119.7C37—C42—C41121.4 (3)
C14—C15—H15119.7C37—C42—H42119.3
C15—C16—C17120.0 (4)C41—C42—H42119.3
C15—C16—H16120.0C44—C43—C26114.6 (2)
C17—C16—H16120.0C44—C43—H43A108.6
C16—C17—C12120.4 (3)C26—C43—H43A108.6
C16—C17—H17119.8C44—C43—H43B108.6
C12—C17—H17119.8C26—C43—H43B108.6
C19—C18—C1116.0 (2)H43A—C43—H43B107.6
C19—C18—H18A108.3O4—C44—C45120.3 (3)
C1—C18—H18A108.3O4—C44—C43121.5 (3)
C19—C18—H18B108.3C45—C44—C43118.2 (3)
C1—C18—H18B108.3C46—C45—C50118.9 (3)
H18A—C18—H18B107.4C46—C45—C44122.4 (3)
O2—C19—C20120.8 (3)C50—C45—C44118.6 (3)
O2—C19—C18121.3 (3)C45—C46—C47120.5 (3)
C20—C19—C18117.9 (3)C45—C46—H46119.8
C21—C20—C25118.2 (3)C47—C46—H46119.8
C21—C20—C19118.8 (3)C48—C47—C46120.0 (4)
C25—C20—C19123.1 (3)C48—C47—H47120.0
C22—C21—C20121.6 (3)C46—C47—H47120.0
C22—C21—H21119.2C49—C48—C47120.3 (4)
C20—C21—H21119.2C49—C48—H48119.8
C23—C22—C21119.9 (3)C47—C48—H48119.8
C23—C22—H22120.1CG1—C48—H48179.5
C21—C22—H22120.1C48—C49—C50120.6 (4)
C22—C23—C24119.9 (3)C48—C49—H49119.7
C22—C23—H23120.1C50—C49—H49119.7
C24—C23—H23120.1C49—C50—C45119.7 (4)
C23—C24—C25120.0 (3)C49—C50—H50120.2
C23—C24—H24120.0C45—C50—H50120.2
C25—C24—H24120.0

Symmetry codes: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C46—H46···O10.932.513.436 (4)172
C23—H23···Cg2ii0.932.673.535 (4)155

Symmetry codes: (ii) x, y+1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2435).

References

  • Bose, A. K., Pednekar, S., Ganguly, S. N., Chakraborty, G. & Manhas, M. S. (2004). Tetrahedron Lett.45, 8351–8353..
  • Das, G. C., Hursthouse, M. B., Malik, K. M. A., Rahman, M. M., Rahman, M. T. & Olsson, T. (1994). J. Chem. Cryst.24, 511–515.
  • Huang, X.-Q., Wang, D.-Q., Dou, J.-M. & Wang, J.-X. (2006). Acta Cryst. E62, o60–o61.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

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