organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

1-Benzyl-3-(2-furylmeth­yl)-1,2,3,4,5,6-hexa­hydro­spiro­[benzo[h]quinazoline-5,1′-cyclo­hexa­ne]-2,4-dione

aMolecular Structure Research Center, National Academy of Sciences RA, Azatutyan ave. 26, 375014 Yerevan, Republic of Armenia, and bInstitute of Fine Organic Chemistry, National Academy of Sciences RA, Azatutyan ave. 26, 375014 Yerevan, Republic of Armenia
*Correspondence e-mail: rafael@msrc.am

(Received 13 March 2008; accepted 19 March 2008; online 29 March 2008)

The title compound, C29H28N2O3, displays anti­depressant and anti­cancer activities. The furan ring is disordered over two orientations [site occupancies 0.690 (12)/0.310 (12)] related by a rotation of 180°. The ring conformations are chair for the cyclo­hexane ring, boat for the cyclo­hexa­diene ring and twist for the pyrimidine ring. The crystal packing is determined solely by van der Waals inter­actions.

Related literature

For the synthesis and biological properties of related compounds, see: Markosyan et al. (1991[Markosyan, A. I., Kuroyan, R. H., Hovhanisyan, M. H., Sukasyan, R. S., Arzanunts, E. M., Sarkisyan, I. S., Chachoyan, A. A. & Gharibdjanyan, B. T. (1991). Khim. Farm. Zh. 25, 18-21.], 1995[Markosyan, A. I., Dilanyan, S. V., Kuroyan, R. H., Chachoyan, A. A. & Gharibdjanyan, B. T. (1995). Khim. Farm. Zh. 29, 32-34.]). For reference structural data, see: Markosyan et al. (1999[Markosyan, A. I., Kuroyan, R. H., Dilanyan, S. V., Hovhanisyan, A. Sh., Karapetyan, H. A. & Struchkov, Yu. T. (1999). Chem. Heterocycl. C. (Latvia), 35, 105-110.], 2000[Markosyan, A. I., Kuroyan, R. H., Dilanyan, S. V., Alexanyan, M. S., Karapetyan, H. A. & Struchkov, Yu. T. (2000). Chem. Heterocycl. C. (Latvia), 36, 658-662.]). For related literature, see: Kuroyan et al. (1989[Kuroyan, R. H., Markosyan, A. I., Hovhannisyan, A. Sh. & Hovhannisyan, M. H. (1989). Armenian Chem. J. 42, 527-529.]).

[Scheme 1]

Experimental

Crystal data
  • C29H28N2O3

  • Mr = 452.53

  • Triclinic, [P \overline 1]

  • a = 10.615 (2) Å

  • b = 11.472 (2) Å

  • c = 11.923 (2) Å

  • α = 109.90 (2)°

  • β = 97.95 (2)°

  • γ = 115.41 (2)°

  • V = 1162.0 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 293 (2) K

  • 0.42 × 0.4 × 0.3 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: none

  • 7089 measured reflections

  • 6747 independent reflections

  • 4438 reflections with I > 2σ(I)

  • Rint = 0.012

  • 3 standard reflections frequency: 180 min intensity decay: none

Refinement
  • R[F2 > 2σ(F2)] = 0.060

  • wR(F2) = 0.148

  • S = 1.14

  • 6747 reflections

  • 444 parameters

  • 13 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.19 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1988[Enraf-Nonius (1988). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: HELENA (Meetsma & Spek, 2000[Meetsma, A. & Spek, A. L. (2000). HELENA. University of Groningen, The Netherlands.]; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The title compound (Fig. 1) shows antidepressant and anticancer activities. All the bond lengths and angles are in good agreement with reference values (Allen et al., 1995). In the crystal structure the two orientations of furan ring are observed in the ratio 0.7 : 0.3, which are related by rotation about C29—C30 bond for 180° (Fig. 2). The crystal packing is realised through van der Waals interactions (Fig. 3).

Related literature top

For the synthesis and biological properties of related compounds, see: Markosyan et al. (1991, 1995). For reference structural data, see: Markosyan et al. (1999, 2000). For related literature, see: Kuroyan et al. (1989).

Experimental top

The title compound was synthesized in the three step reaction: (i) The mixture of 28.5 g (0.1 mol) 4-amino-3-ethoxycarbonyl-1,2- dihydrospiro(naphtalene-2,1'-cyclohexane) (Kuroyan et al. 1989) and 15.6 g (0.1 mol) phenylchloroformate in 100 ml dry benzene was boiled with back-flow condenser for 7 h. After solvent distillation the residue phenylester of 3-ethoxicarbonyl-1,2-dihydrospiro(naphtalene-2,1'-cyclohexane) -2-carbaminic acid was recrystallized from mixture ethanol-water (3: 1); (ii) The mixture of 4.0 g (0,01 mol) phenylester of 3-ethoxicarbonyl- 1,2-dihydrospiro(naphtalene-2,1'-cyclohexane)-2-carbaminic acid and 9.71 g (0.01 mol) furan-2-ylmethylamine in 20 ml absolute ethanol was boiled with back-flow condenser for 7 h. To the reaction mixture 1.1 g (0.02 mol) KOH in 10 ml water was added and again boiled for 3 h. The reaction mixture was cooled to 283 K and acidulated by HCl. (iii) The mixture of 1.81 g (0.005 mol) 3-(furan-2-ylmethyl)-1,2,3,4,5,6-hexahydrospiro(benzo[h]quinazoline- 5,1'-cyclohexane)-2,4-dione, 0.34 g (0.006 mol) KOH, and 0.64 g (0.005 mol) benzylchloride in 30 ml absolute ethanol was boiled with back-flow condenser for 10 h. After cooling to room temperature 20 ml water was added and the precipitate of 1-benzyl-3-(furan-2-ylmethyl)-1,2,3,4,5,6-hexahydrospiro(benzo[h]quinazoline- 5,1'-cyclohexane)-2,4-dione was filtered off and recrystallized from butanole.

Refinement top

The analysis of difference Fourier maps indicated disorder for furan group. Because of disorder of furan ring (C31, C32, C33 and O34) SADI instructions were aplied on corresponding interatomic distances in furan ring. The H atom positions except of those belonging to furan ring were determined from difference Fourier maps and their positions and Uiso values were freely refined. H atoms of furan group were positioned geometrically and refined using a riding model with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1988); cell refinement: CAD-4 Software (Enraf–Nonius, 1988); data reduction: HELENA (Meetsma & Spek, 2000; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure with displacement ellipsoids drawn at the 50% probability level (H atoms omitted for clarity).
[Figure 2] Fig. 2. A disorder model of furan ring.
[Figure 3] Fig. 3. The crystal packing of I via van der Waals interactions, only.
1-Benzyl-3-(2-furylmethyl)-1,2,3,4,5,6- hexahydrospiro[benzo[h]quinazoline-5,1'-cyclohexane]-2,4-dione top
Crystal data top
C29H28N2O3Z = 2
Mr = 452.53F(000) = 480
Triclinic, P1Dx = 1.293 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.615 (2) ÅCell parameters from 22 reflections
b = 11.472 (2) Åθ = 13–16°
c = 11.923 (2) ŵ = 0.08 mm1
α = 109.90 (2)°T = 293 K
β = 97.95 (2)°Prism, colourless
γ = 115.41 (2)°0.42 × 0.4 × 0.3 mm
V = 1162.0 (5) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.012
Radiation source: fine-focus sealed tubeθmax = 30.0°, θmin = 1.9°
Graphite monochromatorh = 014
θ/2θ scansk = 1614
7089 measured reflectionsl = 1616
6747 independent reflections3 standard reflections every 180 min
4438 reflections with I > 2σ(I) intensity decay: none
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)] = 0.060Hydrogen site location: difference Fourier map
wR(F2) = 0.148H atoms treated by a mixture of independent and constrained refinement
S = 1.14 w = 1/[σ2(Fo2) + (0.0526P)2 + 0.5819P]
where P = (Fo2 + 2Fc2)/3
6747 reflections(Δ/σ)max < 0.001
444 parametersΔρmax = 0.20 e Å3
13 restraintsΔρmin = 0.19 e Å3
Crystal data top
C29H28N2O3γ = 115.41 (2)°
Mr = 452.53V = 1162.0 (5) Å3
Triclinic, P1Z = 2
a = 10.615 (2) ÅMo Kα radiation
b = 11.472 (2) ŵ = 0.08 mm1
c = 11.923 (2) ÅT = 293 K
α = 109.90 (2)°0.42 × 0.4 × 0.3 mm
β = 97.95 (2)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.012
7089 measured reflections3 standard reflections every 180 min
6747 independent reflections intensity decay: none
4438 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.06013 restraints
wR(F2) = 0.148H atoms treated by a mixture of independent and constrained refinement
S = 1.14Δρmax = 0.20 e Å3
6747 reflectionsΔρmin = 0.19 e Å3
444 parameters
Special details top

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)
N11.08120 (15)0.21666 (16)0.48300 (13)0.0419 (3)
C21.13299 (19)0.14849 (19)0.39899 (17)0.0449 (4)
N31.04486 (15)0.07554 (16)0.27309 (14)0.0432 (3)
C40.89672 (18)0.03776 (19)0.23022 (17)0.0420 (4)
C50.83797 (18)0.08654 (18)0.32815 (16)0.0394 (4)
C60.93588 (18)0.18943 (19)0.44529 (16)0.0395 (4)
C70.8947 (2)0.2859 (2)0.52898 (16)0.0444 (4)
C80.9960 (3)0.4318 (2)0.60849 (18)0.0532 (5)
H81.099 (2)0.470 (2)0.6160 (19)0.053 (6)*
C90.9475 (3)0.5213 (3)0.6720 (2)0.0674 (6)
H91.022 (3)0.625 (3)0.730 (3)0.096 (9)*
C100.7987 (4)0.4663 (3)0.6557 (2)0.0754 (8)
H100.763 (3)0.529 (3)0.702 (3)0.094 (9)*
C110.6971 (3)0.3226 (3)0.5753 (2)0.0657 (6)
H110.594 (3)0.281 (2)0.560 (2)0.070 (7)*
C120.7436 (2)0.2304 (2)0.51091 (18)0.0505 (5)
C130.6409 (2)0.0748 (3)0.4216 (2)0.0543 (5)
H13A0.539 (3)0.051 (2)0.404 (2)0.063 (6)*
H13B0.650 (2)0.012 (2)0.458 (2)0.066 (7)*
C140.67232 (18)0.0313 (2)0.29541 (17)0.0417 (4)
C150.6232 (2)0.0922 (2)0.21252 (19)0.0457 (4)
H15A0.670 (2)0.196 (2)0.2642 (18)0.047 (5)*
H15B0.662 (2)0.077 (2)0.1407 (18)0.045 (5)*
C160.4546 (2)0.0179 (3)0.1570 (2)0.0569 (5)
H16A0.413 (2)0.041 (2)0.226 (2)0.066 (7)*
H16B0.433 (2)0.060 (2)0.102 (2)0.061 (6)*
C170.3820 (2)0.1444 (3)0.0866 (2)0.0623 (6)
H17A0.276 (3)0.190 (2)0.052 (2)0.062 (6)*
H17B0.416 (2)0.170 (2)0.012 (2)0.060 (6)*
C180.4207 (2)0.2040 (3)0.1724 (3)0.0637 (6)
H18A0.377 (3)0.311 (3)0.127 (2)0.076 (7)*
H18B0.379 (3)0.187 (2)0.242 (2)0.070 (7)*
C190.5887 (2)0.1354 (2)0.2251 (2)0.0549 (5)
H19A0.626 (2)0.163 (2)0.154 (2)0.063 (7)*
H19B0.614 (2)0.172 (2)0.286 (2)0.069 (7)*
O201.25037 (15)0.15498 (16)0.43382 (14)0.0613 (4)
O210.83070 (15)0.02697 (16)0.11618 (12)0.0576 (4)
C221.1571 (2)0.2637 (2)0.61735 (18)0.0465 (4)
H22A1.172 (2)0.185 (2)0.6173 (19)0.052 (6)*
H22B1.088 (2)0.270 (2)0.6644 (19)0.053 (6)*
C231.30282 (19)0.40402 (19)0.68204 (16)0.0432 (4)
C241.3708 (3)0.4532 (2)0.80950 (19)0.0587 (5)
H241.322 (2)0.397 (2)0.854 (2)0.066 (7)*
C251.5049 (3)0.5808 (3)0.8754 (2)0.0734 (7)
H251.544 (3)0.612 (3)0.966 (3)0.101 (9)*
C261.5726 (3)0.6612 (3)0.8161 (2)0.0684 (7)
H261.669 (3)0.753 (3)0.865 (2)0.081 (7)*
C271.5061 (3)0.6136 (3)0.6900 (2)0.0652 (6)
H271.550 (3)0.667 (3)0.644 (2)0.085 (8)*
C281.3712 (2)0.4848 (2)0.6228 (2)0.0562 (5)
H281.325 (3)0.451 (3)0.534 (2)0.074 (7)*
C291.1047 (2)0.0178 (2)0.17737 (19)0.0465 (4)
H29A1.079 (2)0.038 (2)0.104 (2)0.061 (6)*
H29B1.209 (2)0.072 (2)0.217 (2)0.056 (6)*
C301.0443 (2)0.1381 (2)0.13117 (17)0.0478 (4)
C310.9483 (10)0.2341 (9)0.0171 (7)0.088 (3)0.690 (12)
H310.90640.21830.04590.105*0.690 (12)
C320.9225 (10)0.3754 (10)0.0129 (10)0.098 (3)0.690 (12)
H320.86490.46660.05530.118*0.690 (12)
C330.9995 (11)0.3411 (8)0.1272 (8)0.096 (4)0.690 (12)
H330.99680.40910.15410.116*0.690 (12)
O341.0839 (7)0.1958 (6)0.2025 (5)0.0702 (19)0.690 (12)
O34A0.9428 (10)0.2586 (10)0.0228 (9)0.069 (4)0.310 (12)
C31A1.1165 (16)0.1635 (14)0.2101 (15)0.043 (3)0.310 (12)
H31A1.19210.09670.28710.052*0.310 (12)
C33A0.9426 (18)0.3671 (17)0.046 (2)0.091 (8)0.310 (12)
H33A0.87240.46380.00580.109*0.310 (12)
C32A1.0492 (16)0.3246 (14)0.1478 (17)0.061 (3)0.310 (12)
H32A1.07630.38040.17460.073*0.310 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0344 (7)0.0459 (8)0.0370 (7)0.0204 (6)0.0044 (6)0.0127 (6)
C20.0342 (8)0.0422 (9)0.0465 (10)0.0186 (7)0.0052 (7)0.0119 (8)
N30.0328 (7)0.0456 (8)0.0415 (8)0.0208 (6)0.0086 (6)0.0098 (6)
C40.0336 (8)0.0414 (9)0.0445 (9)0.0200 (7)0.0071 (7)0.0133 (8)
C50.0321 (8)0.0429 (9)0.0429 (9)0.0211 (7)0.0095 (7)0.0174 (7)
C60.0386 (8)0.0425 (9)0.0400 (9)0.0225 (7)0.0122 (7)0.0193 (7)
C70.0543 (10)0.0537 (11)0.0363 (9)0.0344 (9)0.0166 (8)0.0223 (8)
C80.0695 (14)0.0562 (12)0.0409 (10)0.0380 (11)0.0195 (9)0.0211 (9)
C90.101 (2)0.0645 (15)0.0490 (12)0.0547 (15)0.0256 (13)0.0226 (11)
C100.115 (2)0.095 (2)0.0566 (14)0.0813 (19)0.0412 (15)0.0354 (14)
C110.0774 (16)0.102 (2)0.0561 (13)0.0665 (16)0.0361 (12)0.0431 (14)
C120.0579 (11)0.0719 (13)0.0422 (10)0.0430 (11)0.0236 (9)0.0315 (10)
C130.0416 (10)0.0761 (15)0.0568 (12)0.0321 (10)0.0223 (9)0.0369 (11)
C140.0306 (8)0.0490 (10)0.0476 (10)0.0218 (7)0.0120 (7)0.0225 (8)
C150.0406 (9)0.0538 (11)0.0487 (10)0.0279 (9)0.0146 (8)0.0245 (9)
C160.0431 (10)0.0814 (16)0.0610 (13)0.0392 (11)0.0172 (9)0.0376 (12)
C170.0341 (10)0.0795 (16)0.0625 (14)0.0240 (10)0.0091 (9)0.0298 (12)
C180.0361 (10)0.0613 (14)0.0780 (16)0.0150 (10)0.0098 (10)0.0311 (12)
C190.0364 (9)0.0485 (11)0.0710 (14)0.0184 (9)0.0077 (9)0.0257 (10)
O200.0404 (7)0.0691 (9)0.0610 (9)0.0328 (7)0.0034 (6)0.0136 (7)
O210.0463 (7)0.0715 (9)0.0397 (7)0.0336 (7)0.0043 (6)0.0082 (6)
C220.0413 (10)0.0501 (11)0.0410 (9)0.0202 (9)0.0054 (8)0.0201 (8)
C230.0417 (9)0.0427 (9)0.0380 (9)0.0222 (8)0.0055 (7)0.0127 (7)
C240.0644 (13)0.0550 (12)0.0400 (10)0.0236 (10)0.0025 (9)0.0185 (9)
C250.0755 (16)0.0595 (14)0.0471 (12)0.0223 (12)0.0109 (11)0.0117 (11)
C260.0519 (12)0.0483 (12)0.0713 (15)0.0160 (10)0.0048 (11)0.0138 (11)
C270.0569 (13)0.0543 (13)0.0678 (14)0.0181 (11)0.0167 (11)0.0248 (11)
C280.0536 (12)0.0540 (12)0.0439 (11)0.0179 (10)0.0086 (9)0.0196 (9)
C290.0356 (9)0.0496 (11)0.0483 (10)0.0223 (8)0.0151 (8)0.0144 (9)
C300.0433 (10)0.0529 (11)0.0508 (11)0.0299 (9)0.0204 (8)0.0181 (9)
C310.116 (6)0.060 (3)0.081 (5)0.046 (4)0.023 (4)0.028 (3)
C320.098 (6)0.048 (3)0.104 (5)0.017 (3)0.050 (5)0.008 (3)
C330.146 (10)0.101 (6)0.145 (8)0.096 (7)0.116 (8)0.095 (6)
O340.110 (4)0.067 (3)0.062 (3)0.055 (3)0.048 (2)0.039 (3)
O34A0.036 (3)0.041 (5)0.079 (6)0.021 (3)0.024 (4)0.014 (4)
C31A0.041 (4)0.029 (4)0.044 (5)0.012 (3)0.010 (3)0.010 (3)
C33A0.045 (5)0.044 (6)0.130 (16)0.028 (5)0.011 (8)0.011 (8)
C32A0.053 (5)0.047 (5)0.091 (7)0.033 (4)0.043 (5)0.022 (5)
Geometric parameters (Å, º) top
N1—C21.380 (2)C18—H18A1.00 (3)
N1—C61.406 (2)C18—H18B1.00 (2)
N1—C221.479 (2)C19—H19A1.00 (2)
C2—O201.219 (2)C19—H19B1.01 (2)
C2—N31.383 (2)C22—C231.505 (3)
N3—C41.401 (2)C22—H22A0.98 (2)
N3—C291.480 (2)C22—H22B0.99 (2)
C4—O211.222 (2)C23—C281.376 (3)
C4—C51.457 (2)C23—C241.383 (3)
C5—C61.359 (2)C24—C251.380 (3)
C5—C141.527 (2)C24—H240.99 (2)
C6—C71.482 (2)C25—C261.373 (4)
C7—C81.397 (3)C25—H250.97 (3)
C7—C121.400 (3)C26—C271.369 (3)
C8—C91.388 (3)C26—H261.00 (3)
C8—H80.96 (2)C27—C281.392 (3)
C9—C101.380 (4)C27—H270.97 (3)
C9—H91.00 (3)C28—H280.97 (2)
C10—C111.382 (4)C29—C301.471 (3)
C10—H101.00 (3)C29—H29A1.01 (2)
C11—C121.397 (3)C29—H29B0.95 (2)
C11—H110.95 (2)C30—C31A1.317 (6)
C12—C131.491 (3)C30—C311.317 (6)
C13—C141.548 (3)C30—O341.363 (4)
C13—H13A0.96 (2)C30—O34A1.364 (4)
C13—H13B0.99 (2)C31—C321.505 (8)
C14—C151.541 (3)C31—H310.9300
C14—C191.547 (3)C32—C331.316 (6)
C15—C161.532 (3)C32—H320.9300
C15—H15A0.98 (2)C33—O341.365 (4)
C15—H15B0.99 (2)C33—H330.9300
C16—C171.513 (4)O34A—C33A1.365 (4)
C16—H16A1.00 (2)C31A—C32A1.505 (8)
C16—H16B0.99 (2)C31A—H31A0.9300
C17—C181.511 (3)C33A—C32A1.316 (6)
C17—H17A0.97 (2)C33A—H33A0.9300
C17—H17B1.00 (2)C32A—H32A0.9300
C18—C191.531 (3)
C2—N1—C6121.11 (14)C19—C18—H18A107.3 (14)
C2—N1—C22114.30 (15)C17—C18—H18B109.7 (14)
C6—N1—C22119.42 (15)C19—C18—H18B111.1 (13)
O20—C2—N1121.86 (17)H18A—C18—H18B106.0 (19)
O20—C2—N3122.46 (17)C18—C19—C14113.22 (18)
N1—C2—N3115.66 (15)C18—C19—H19A109.4 (13)
C2—N3—C4124.67 (15)C14—C19—H19A107.7 (13)
C2—N3—C29117.84 (14)C18—C19—H19B109.9 (13)
C4—N3—C29117.07 (15)C14—C19—H19B108.3 (13)
O21—C4—N3118.32 (16)H19A—C19—H19B108.2 (18)
O21—C4—C5126.01 (16)N1—C22—C23116.35 (16)
N3—C4—C5115.61 (15)N1—C22—H22A104.9 (12)
C6—C5—C4117.92 (15)C23—C22—H22A109.7 (12)
C6—C5—C14121.80 (16)N1—C22—H22B107.8 (12)
C4—C5—C14120.10 (15)C23—C22—H22B109.3 (12)
C5—C6—N1121.11 (16)H22A—C22—H22B108.6 (17)
C5—C6—C7119.36 (15)C28—C23—C24118.73 (19)
N1—C6—C7119.14 (16)C28—C23—C22124.40 (17)
C8—C7—C12120.01 (18)C24—C23—C22116.87 (18)
C8—C7—C6122.61 (18)C25—C24—C23120.3 (2)
C12—C7—C6116.64 (17)C25—C24—H24120.1 (13)
C9—C8—C7120.1 (2)C23—C24—H24119.6 (14)
C9—C8—H8120.7 (13)C26—C25—C24120.8 (2)
C7—C8—H8119.2 (12)C26—C25—H25122.8 (17)
C10—C9—C8119.9 (3)C24—C25—H25116.4 (17)
C10—C9—H9121.0 (16)C27—C26—C25119.4 (2)
C8—C9—H9119.0 (17)C27—C26—H26120.6 (15)
C9—C10—C11120.5 (2)C25—C26—H26120.0 (15)
C9—C10—H10120.7 (16)C26—C27—C28120.2 (2)
C11—C10—H10118.9 (16)C26—C27—H27122.2 (16)
C10—C11—C12120.6 (2)C28—C27—H27117.7 (16)
C10—C11—H11123.3 (15)C23—C28—C27120.6 (2)
C12—C11—H11116.1 (15)C23—C28—H28119.3 (14)
C11—C12—C7118.9 (2)C27—C28—H28120.0 (14)
C11—C12—C13123.8 (2)C30—C29—N3112.69 (16)
C7—C12—C13117.29 (17)C30—C29—H29A109.4 (12)
C12—C13—C14112.36 (17)N3—C29—H29A107.8 (12)
C12—C13—H13A111.2 (13)C30—C29—H29B112.1 (13)
C14—C13—H13A109.3 (13)N3—C29—H29B105.6 (13)
C12—C13—H13B111.5 (13)H29A—C29—H29B109.0 (17)
C14—C13—H13B106.2 (13)C31A—C30—C31125.7 (9)
H13A—C13—H13B106.0 (18)C31—C30—O34114.2 (5)
C5—C14—C15111.34 (15)O34—C30—O34A101.9 (6)
C5—C14—C19107.97 (15)C31A—C30—C29110.5 (6)
C15—C14—C19110.40 (16)C31—C30—C29123.0 (5)
C5—C14—C13107.42 (15)O34—C30—C29122.9 (3)
C15—C14—C13111.66 (16)O34A—C30—C29135.2 (6)
C19—C14—C13107.89 (17)C30—C31—C32103.6 (7)
C16—C15—C14112.83 (17)C30—C31—H31128.2
C16—C15—H15A112.2 (11)C32—C31—H31128.2
C14—C15—H15A107.6 (11)C33—C32—C31104.7 (8)
C16—C15—H15B107.7 (11)C33—C32—H32127.7
C14—C15—H15B108.5 (11)C31—C32—H32127.7
H15A—C15—H15B107.9 (15)C32—C33—O34113.3 (7)
C17—C16—C15111.99 (18)C32—C33—H33123.4
C17—C16—H16A108.3 (13)O34—C33—H33123.4
C15—C16—H16A109.8 (13)C30—O34—C33103.9 (4)
C17—C16—H16B112.1 (12)C30—O34A—C33A102.7 (10)
C15—C16—H16B107.4 (12)C30—C31A—C32A104.6 (10)
H16A—C16—H16B107.2 (18)C30—C31A—H31A127.7
C18—C17—C16110.7 (2)C32A—C31A—H31A127.7
C18—C17—H17A110.2 (13)C32A—C33A—O34A115.0 (15)
C16—C17—H17A110.9 (13)C32A—C33A—H33A122.5
C18—C17—H17B109.5 (13)O34A—C33A—H33A122.5
C16—C17—H17B109.6 (13)C33A—C32A—C31A102.8 (15)
H17A—C17—H17B105.7 (18)C33A—C32A—H32A128.6
C17—C18—C19110.35 (19)C31A—C32A—H32A128.6
C17—C18—H18A112.3 (14)
C6—N1—C2—O20169.53 (18)C5—C14—C15—C16169.10 (17)
C22—N1—C2—O2015.1 (3)C19—C14—C15—C1649.2 (2)
C6—N1—C2—N311.9 (3)C13—C14—C15—C1670.8 (2)
C22—N1—C2—N3166.29 (16)C14—C15—C16—C1753.5 (2)
O20—C2—N3—C4165.43 (19)C15—C16—C17—C1857.6 (3)
N1—C2—N3—C416.0 (3)C16—C17—C18—C1958.2 (3)
O20—C2—N3—C296.9 (3)C17—C18—C19—C1456.0 (3)
N1—C2—N3—C29171.69 (16)C5—C14—C19—C18172.93 (19)
C2—N3—C4—O21179.91 (18)C15—C14—C19—C1851.0 (3)
C29—N3—C4—O217.5 (3)C13—C14—C19—C1871.3 (2)
C2—N3—C4—C52.8 (3)C2—N1—C22—C2381.6 (2)
C29—N3—C4—C5175.20 (16)C6—N1—C22—C23123.49 (18)
O21—C4—C5—C6162.17 (19)N1—C22—C23—C283.5 (3)
N3—C4—C5—C614.9 (2)N1—C22—C23—C24176.44 (18)
O21—C4—C5—C1413.0 (3)C28—C23—C24—C250.3 (3)
N3—C4—C5—C14169.97 (15)C22—C23—C24—C25179.7 (2)
C4—C5—C6—N119.1 (3)C23—C24—C25—C260.4 (4)
C14—C5—C6—N1165.81 (16)C24—C25—C26—C270.3 (4)
C4—C5—C6—C7153.65 (16)C25—C26—C27—C280.1 (4)
C14—C5—C6—C721.4 (3)C24—C23—C28—C270.0 (3)
C2—N1—C6—C55.5 (3)C22—C23—C28—C27180.0 (2)
C22—N1—C6—C5147.66 (17)C26—C27—C28—C230.1 (4)
C2—N1—C6—C7167.29 (16)C2—N3—C29—C30101.6 (2)
C22—N1—C6—C739.6 (2)C4—N3—C29—C3071.3 (2)
C5—C6—C7—C8142.40 (19)N3—C29—C30—C31A82.3 (10)
N1—C6—C7—C830.5 (3)N3—C29—C30—C31107.7 (7)
C5—C6—C7—C1227.8 (2)N3—C29—C30—O3472.8 (4)
N1—C6—C7—C12159.32 (16)N3—C29—C30—O34A104.9 (8)
C12—C7—C8—C91.5 (3)C31A—C30—C31—C3210.5 (15)
C6—C7—C8—C9171.33 (18)O34—C30—C31—C320.6 (10)
C7—C8—C9—C100.5 (3)O34A—C30—C31—C3210 (4)
C8—C9—C10—C110.8 (4)C29—C30—C31—C32178.9 (5)
C9—C10—C11—C121.1 (4)C30—C31—C32—C333.9 (11)
C10—C11—C12—C70.1 (3)C31—C32—C33—O346.0 (11)
C10—C11—C12—C13179.3 (2)C31A—C30—O34—C33145 (5)
C8—C7—C12—C111.2 (3)C31—C30—O34—C332.8 (9)
C6—C7—C12—C11171.64 (17)O34A—C30—O34—C330.7 (8)
C8—C7—C12—C13178.10 (18)C29—C30—O34—C33177.7 (4)
C6—C7—C12—C137.7 (2)C32—C33—O34—C305.6 (10)
C11—C12—C13—C14132.1 (2)C31A—C30—O34A—C33A7.5 (16)
C7—C12—C13—C1447.2 (2)C31—C30—O34A—C33A169 (5)
C6—C5—C14—C15105.2 (2)O34—C30—O34A—C33A1.9 (13)
C4—C5—C14—C1569.8 (2)C29—C30—O34A—C33A179.9 (11)
C6—C5—C14—C19133.43 (19)C31—C30—C31A—C32A7 (2)
C4—C5—C14—C1951.6 (2)O34—C30—C31A—C32A36 (4)
C6—C5—C14—C1317.3 (2)O34A—C30—C31A—C32A2.5 (18)
C4—C5—C14—C13167.71 (17)C29—C30—C31A—C32A177.0 (10)
C12—C13—C14—C549.9 (2)C30—O34A—C33A—C32A10 (2)
C12—C13—C14—C1572.5 (2)O34A—C33A—C32A—C31A9 (3)
C12—C13—C14—C19166.05 (16)C30—C31A—C32A—C33A4 (2)

Experimental details

Crystal data
Chemical formulaC29H28N2O3
Mr452.53
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)10.615 (2), 11.472 (2), 11.923 (2)
α, β, γ (°)109.90 (2), 97.95 (2), 115.41 (2)
V3)1162.0 (5)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.42 × 0.4 × 0.3
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
7089, 6747, 4438
Rint0.012
(sin θ/λ)max1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.148, 1.14
No. of reflections6747
No. of parameters444
No. of restraints13
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.20, 0.19

Computer programs: CAD-4 Software (Enraf–Nonius, 1988), HELENA (Meetsma & Spek, 2000, SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

References

First citationEnraf–Nonius (1988). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
First citationKuroyan, R. H., Markosyan, A. I., Hovhannisyan, A. Sh. & Hovhannisyan, M. H. (1989). Armenian Chem. J. 42, 527–529.  CAS Google Scholar
First citationMarkosyan, A. I., Dilanyan, S. V., Kuroyan, R. H., Chachoyan, A. A. & Gharibdjanyan, B. T. (1995). Khim. Farm. Zh. 29, 32–34.  Google Scholar
First citationMarkosyan, A. I., Kuroyan, R. H., Dilanyan, S. V., Alexanyan, M. S., Karapetyan, H. A. & Struchkov, Yu. T. (2000). Chem. Heterocycl. C. (Latvia), 36, 658–662.  Google Scholar
First citationMarkosyan, A. I., Kuroyan, R. H., Dilanyan, S. V., Hovhanisyan, A. Sh., Karapetyan, H. A. & Struchkov, Yu. T. (1999). Chem. Heterocycl. C. (Latvia), 35, 105–110.  Google Scholar
First citationMarkosyan, A. I., Kuroyan, R. H., Hovhanisyan, M. H., Sukasyan, R. S., Arzanunts, E. M., Sarkisyan, I. S., Chachoyan, A. A. & Gharibdjanyan, B. T. (1991). Khim. Farm. Zh. 25, 18–21.  CAS Google Scholar
First citationMeetsma, A. & Spek, A. L. (2000). HELENA. University of Groningen, The Netherlands.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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