13-Hydr­oxy-4,16-dimethyl-4,16-diaza­penta­cyclo­[12.3.1.01,5.05,13.07,12]octa­deca-7(12),8,10-triene-6,18-dione

Suresh, J.; Gurunathan, K.; Kumar, R.S.; Perumal, S.; Lakshman, P.L.N.

doi:10.1107/S1600536809015293

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 5| May 2009| Pages o1163-o1164

doi:10.1107/S1600536809015293

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access

13-Hydroxy-4,16-dimethyl-4,16-diazapentacyclo[12.3.1.0^1,5.0^5,13.0^7,12]octadeca-7(12),8,10-triene-6,18-dione

J. Suresh,^a K. Gurunathan,^a R. Suresh Kumar,^b S. Perumal ^b and P. L. Nilantha Lakshman ^c ^*

^aDepartment of Physics, The Madura College, Madurai 625 011, India, ^bSchool of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, and ^cDepartment of Food Science and Technology, Faculty of Agriculture, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
^*Correspondence e-mail: nilanthalakshman@yahoo.co.uk

(Received 20 April 2009; accepted 23 April 2009; online 30 April 2009)

In the title compound, C₁₈H₂₀N₂O₃, the N-methylpiperidone ring adopts a chair conformation. The pyrrolidine ring and the five-membered cyclopentane rings adopt envelope conformations. The five-membered ring of the ninhydrin system adopts an envelope conformation with the central C atom deviating by 0.217 (1)Å from the mean plane through the other atoms. The molecular packing is characterized by intermolecular C—H⋯O and intramolecular C—H⋯O and O—H⋯N interactions.

Related literature

For the cytotoxic and anticancer properties of piperidinones, see: Dimmock et al. (1990 , 2001 ). Piperidinone derivatives have attracted attention due to their predicted mode of interaction with cellular thiols, having little or no affinity for the hydroxy and amino groups found in nucleic acids, see: Baluja et al. (1964 ); Mutus et al. (1989 ). Ninhydrin is used to monitor deprotection in solid phase peptide synthesis (Kaiser et al., 1970 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₈H₂₀N₂O₃
M_r = 312.36
Monoclinic, P 2₁ /n
a = 11.0862 (5) Å
b = 11.6152 (5) Å
c = 12.5670 (6) Å
β = 102.851 (9)°
V = 1577.70 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.18 × 0.13 × 0.11 mm

Data collection

Nonius MACH-3 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.984, T_max = 0.990
3226 measured reflections
2764 independent reflections
1978 reflections with I > 2σ(I)
R_int = 0.046
2 standard reflections frequency: 60 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.120
S = 1.04
2764 reflections
211 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N2	0.82	2.12	2.655 (2)	123
C18—H18B⋯O3ⁱ	0.96	2.39	3.288 (3)	155
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809015293/at2770sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809015293/at2770Isup2.hkl

checkCIF report

Comment top

Piperidinones belong to an important class of heterocycles which are found to possess a variety of biological activities, including cytotoxic and anticancer properties (Dimmock et al., 1990, 2001). Derivatives of piperidinones have also attracted wide attention from chemists and biologists due to their predicted mode of interaction with cellular thiols, having little or no affinity for the hydroxy and amino groups found in nucleic acids (Baluja et al., 1964; Mutus et al., 1989). Ninhydrin is used to monitor deprotection in solid phase peptide synthesis (Kaiser et al., 1970).

The molecular structure of the title compound is shown in Fig.1. The n-methyl piperidone ring adopts a chair conformation [Q=0.6668 (19) Å, θ= 13.62 (16)°, Φ= 152.0 (7)°; Cremer and Pople, 1975]. The pyrrolidine ring A(N2—C16) and the five membered cyclopentane ring B(C1—C4) adopt envelope conformations [puckering parameters Q=0.327 (2) Å, Φ=178.8 (4)° and Q=0.483 (2) Å, Φ=162.3 (2)° respectively, Cremer and Pople, 1975]. In the ninhydrin system, in the five membered ring the flap atom C7 deviate from the mean plane formed by other atoms C6/C8/C9/C10/C11/C12/C13/C14 by 0.217 (1)Å adopting an envelope conformation. The sum of the angle at the atom N2 is 338.17 (2)° is in accordance with sp³ hybridization.

Fig. 2 shows the packing viewed down the c—axis. The molecular interaction through C—H···O (Table 1) hydrogen bonds, generating a graph set motif of C₁¹(7) along the b—axis, stabilize the crystal structure. There are neither a marked C—H···π nor π···π interactions in the structure.

Related literature top

For the cytotoxic and anticancer properties of piperidinones, see: Dimmock et al. (1990, 2001). Piperidinone derivatives have attracted attention due to their predicted mode of interaction with cellular thiols, having little or no affinity for the hydroxy and amino groups found in nucleic acids, see: Baluja et al. (1964); Mutus et al. (1989). Ninhydrin is used to monitor deprotection in solid phase peptide synthesis (Kaiser et al., 1970). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

A mixture of 1-methyl-4-piperidinone 0.200 g (0.002 mol), ninhydrin 0.315 g (0.002 mol) and sarcosine 0.156 g (0.002 mol) in methanol (30 ml) were refluxed in a water bath for 10 h. After completion of the reaction as monitored by TLC, the excess solvent was removed under vacuum and the residue subjected to flash column chromatography using petroleum ether:ethyl acetate mixture (8:2 v/v) as eluent to obtain crystals of title compound in 8% yield along with a other product. Yield: 8%, melting point: 435–436 K.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. Packing diagram viewed down the c axis.

13-Hydroxy-4,16-dimethyl-4,16- diazapentacyclo[12.3.1.0^1,5.0^5,13.0^7,12]octadeca- 7(12),8,10-triene-6,18-dione top

Crystal data top

C₁₈H₂₀N₂O₃	F(000) = 664
M_r = 312.36	D_x = 1.315 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 11.0862 (5) Å	θ = 2–25°
b = 11.6152 (5) Å	µ = 0.09 mm⁻¹
c = 12.5670 (6) Å	T = 293 K
β = 102.851 (9)°	Needle, colourless
V = 1577.70 (12) Å³	0.18 × 0.13 × 0.11 mm
Z = 4

Data collection top

Nonius MACH-3 diffractometer	1978 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.046
Graphite monochromator	θ_max = 25.0°, θ_min = 2.2°
ω–2θ scans	h = 0→13
Absorption correction: ψ scan (North et al., 1968)	k = −1→13
T_min = 0.984, T_max = 0.990	l = −14→14
3226 measured reflections	2 standard reflections every 60 min
2764 independent reflections	intensity decay: none

Refinement top

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0616P)² + 0.2971P] where P = (F_o² + 2F_c²)/3
2764 reflections	(Δ/σ)_max < 0.001
211 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₈H₂₀N₂O₃	V = 1577.70 (12) Å³
M_r = 312.36	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.0862 (5) Å	µ = 0.09 mm⁻¹
b = 11.6152 (5) Å	T = 293 K
c = 12.5670 (6) Å	0.18 × 0.13 × 0.11 mm
β = 102.851 (9)°

Data collection top

Nonius MACH-3 diffractometer	1978 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.046
T_min = 0.984, T_max = 0.990	2 standard reflections every 60 min
3226 measured reflections	intensity decay: none
2764 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 1.04	Δρ_max = 0.16 e Å⁻³
2764 reflections	Δρ_min = −0.18 e Å⁻³
211 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

	x	y	z	U_iso*/U_eq
C1	0.37990 (16)	0.05350 (16)	0.64487 (16)	0.0558 (5)
C2	0.25684 (15)	0.03912 (14)	0.56351 (16)	0.0496 (4)
C3	0.15940 (16)	0.06258 (15)	0.63055 (15)	0.0517 (4)
H3A	0.0772	0.0460	0.5874	0.062*
H3B	0.1744	0.0143	0.6951	0.062*
C4	0.39217 (16)	0.18110 (16)	0.66421 (15)	0.0537 (5)
H4	0.4750	0.2026	0.7051	0.064*
C5	0.29116 (17)	0.21625 (17)	0.72388 (14)	0.0554 (5)
H5A	0.3067	0.1796	0.7950	0.067*
H5B	0.2935	0.2989	0.7349	0.067*
C6	0.36690 (14)	0.22296 (15)	0.54459 (15)	0.0471 (4)
C7	0.26099 (14)	0.14067 (15)	0.48444 (13)	0.0461 (4)
C8	0.14614 (15)	0.21810 (16)	0.45590 (13)	0.0471 (4)
C9	0.18837 (16)	0.33902 (15)	0.47548 (14)	0.0475 (4)
C10	0.31366 (16)	0.34242 (15)	0.52472 (14)	0.0472 (4)
C11	0.37277 (19)	0.44677 (16)	0.54870 (16)	0.0595 (5)
H11	0.4564	0.4498	0.5824	0.071*
C12	0.3053 (2)	0.54695 (17)	0.52175 (17)	0.0680 (6)
H12	0.3445	0.6178	0.5363	0.082*
C13	0.1808 (2)	0.54309 (18)	0.47352 (17)	0.0688 (6)
H13	0.1369	0.6114	0.4570	0.083*
C14	0.12088 (19)	0.43966 (18)	0.44954 (16)	0.0602 (5)
H14	0.0370	0.4372	0.4167	0.072*
C15	0.24197 (18)	−0.07110 (18)	0.49582 (19)	0.0671 (6)
H15A	0.3119	−0.1222	0.5203	0.080*
H15B	0.1667	−0.1113	0.5006	0.080*
C16	0.2361 (2)	−0.0302 (2)	0.3805 (2)	0.0798 (7)
H16A	0.2811	−0.0824	0.3431	0.096*
H16B	0.1509	−0.0260	0.3397	0.096*
C17	0.2705 (2)	0.1496 (2)	0.28884 (17)	0.0845 (7)
H17A	0.1830	0.1563	0.2602	0.127*
H17B	0.3075	0.1103	0.2369	0.127*
H17C	0.3061	0.2249	0.3025	0.127*
C18	0.06767 (19)	0.2233 (2)	0.70672 (18)	0.0693 (6)
H18A	−0.0089	0.2123	0.6544	0.104*
H18B	0.0787	0.3036	0.7240	0.104*
H18C	0.0660	0.1808	0.7719	0.104*
N1	0.16914 (13)	0.18280 (12)	0.66132 (11)	0.0479 (4)
N2	0.29314 (14)	0.08429 (15)	0.39070 (13)	0.0603 (4)
O1	0.04209 (10)	0.18577 (12)	0.41422 (11)	0.0618 (4)
O2	0.47670 (10)	0.20956 (13)	0.50608 (13)	0.0650 (4)
H2	0.4673	0.1578	0.4606	0.098*
O3	0.45072 (13)	−0.02185 (13)	0.68415 (14)	0.0810 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0474 (10)	0.0498 (11)	0.0671 (12)	0.0042 (8)	0.0059 (9)	0.0104 (9)
C2	0.0446 (9)	0.0392 (9)	0.0636 (11)	−0.0012 (7)	0.0093 (8)	−0.0055 (8)
C3	0.0506 (10)	0.0463 (10)	0.0576 (11)	−0.0046 (8)	0.0110 (8)	0.0019 (8)
C4	0.0431 (9)	0.0535 (11)	0.0569 (11)	−0.0048 (8)	−0.0055 (8)	0.0016 (9)
C5	0.0653 (11)	0.0536 (11)	0.0430 (9)	−0.0058 (9)	0.0026 (8)	0.0004 (8)
C6	0.0342 (8)	0.0477 (10)	0.0585 (10)	−0.0011 (7)	0.0082 (7)	0.0006 (8)
C7	0.0390 (9)	0.0495 (10)	0.0493 (10)	−0.0009 (7)	0.0089 (7)	−0.0065 (8)
C8	0.0395 (9)	0.0594 (11)	0.0416 (9)	0.0023 (8)	0.0073 (7)	0.0001 (8)
C9	0.0505 (10)	0.0509 (10)	0.0434 (9)	0.0056 (8)	0.0150 (7)	0.0053 (8)
C10	0.0504 (10)	0.0472 (10)	0.0463 (9)	−0.0013 (8)	0.0155 (8)	0.0038 (8)
C11	0.0648 (12)	0.0516 (12)	0.0635 (12)	−0.0107 (9)	0.0171 (9)	0.0023 (9)
C12	0.0982 (17)	0.0463 (12)	0.0655 (13)	−0.0053 (11)	0.0311 (12)	0.0055 (10)
C13	0.0958 (17)	0.0522 (13)	0.0640 (13)	0.0185 (11)	0.0300 (12)	0.0143 (10)
C14	0.0639 (12)	0.0639 (13)	0.0544 (11)	0.0184 (10)	0.0168 (9)	0.0104 (9)
C15	0.0553 (11)	0.0494 (11)	0.0965 (16)	−0.0015 (9)	0.0170 (11)	−0.0161 (11)
C16	0.0767 (15)	0.0750 (16)	0.0899 (17)	−0.0090 (11)	0.0229 (12)	−0.0364 (13)
C17	0.0865 (16)	0.117 (2)	0.0548 (13)	0.0058 (14)	0.0251 (11)	−0.0107 (13)
C18	0.0730 (13)	0.0697 (14)	0.0681 (13)	0.0075 (11)	0.0222 (10)	−0.0097 (11)
N1	0.0508 (8)	0.0466 (8)	0.0461 (8)	−0.0003 (6)	0.0105 (6)	−0.0013 (6)
N2	0.0567 (9)	0.0692 (11)	0.0584 (10)	0.0002 (8)	0.0201 (7)	−0.0161 (8)
O1	0.0403 (7)	0.0767 (10)	0.0626 (8)	−0.0001 (6)	−0.0011 (6)	−0.0024 (7)
O2	0.0405 (7)	0.0683 (10)	0.0891 (11)	−0.0026 (6)	0.0207 (6)	−0.0079 (8)
O3	0.0642 (9)	0.0617 (9)	0.1068 (13)	0.0116 (7)	−0.0029 (8)	0.0202 (8)

Geometric parameters (Å, º) top

C1—O3	1.206 (2)	C10—C11	1.379 (3)
C1—C4	1.503 (3)	C11—C12	1.384 (3)
C1—C2	1.521 (2)	C11—H11	0.9300
C2—C15	1.526 (3)	C12—C13	1.379 (3)
C2—C3	1.535 (3)	C12—H12	0.9300
C2—C7	1.549 (3)	C13—C14	1.374 (3)
C3—N1	1.446 (2)	C13—H13	0.9300
C3—H3A	0.9700	C14—H14	0.9300
C3—H3B	0.9700	C15—C16	1.513 (3)
C4—C5	1.535 (3)	C15—H15A	0.9700
C4—C6	1.545 (3)	C15—H15B	0.9700
C4—H4	0.9800	C16—N2	1.466 (3)
C5—N1	1.458 (2)	C16—H16A	0.9700
C5—H5A	0.9700	C16—H16B	0.9700
C5—H5B	0.9700	C17—N2	1.461 (3)
C6—O2	1.415 (2)	C17—H17A	0.9600
C6—C10	1.507 (2)	C17—H17B	0.9600
C6—C7	1.571 (2)	C17—H17C	0.9600
C7—N2	1.460 (2)	C18—N1	1.448 (2)
C7—C8	1.535 (2)	C18—H18A	0.9600
C8—O1	1.2154 (19)	C18—H18B	0.9600
C8—C9	1.484 (3)	C18—H18C	0.9600
C9—C14	1.387 (3)	O2—H2	0.8200
C9—C10	1.390 (2)

O3—C1—C4	128.48 (17)	C11—C10—C6	128.58 (16)
O3—C1—C2	126.90 (18)	C9—C10—C6	111.31 (14)
C4—C1—C2	104.62 (14)	C10—C11—C12	118.75 (19)
C1—C2—C15	115.87 (15)	C10—C11—H11	120.6
C1—C2—C3	104.30 (15)	C12—C11—H11	120.6
C15—C2—C3	116.94 (15)	C13—C12—C11	120.90 (19)
C1—C2—C7	101.38 (13)	C13—C12—H12	119.6
C15—C2—C7	107.23 (16)	C11—C12—H12	119.6
C3—C2—C7	109.99 (14)	C14—C13—C12	120.86 (19)
N1—C3—C2	107.36 (14)	C14—C13—H13	119.6
N1—C3—H3A	110.2	C12—C13—H13	119.6
C2—C3—H3A	110.2	C13—C14—C9	118.43 (19)
N1—C3—H3B	110.2	C13—C14—H14	120.8
C2—C3—H3B	110.2	C9—C14—H14	120.8
H3A—C3—H3B	108.5	C16—C15—C2	104.31 (17)
C1—C4—C5	106.95 (15)	C16—C15—H15A	110.9
C1—C4—C6	99.36 (15)	C2—C15—H15A	110.9
C5—C4—C6	113.42 (14)	C16—C15—H15B	110.9
C1—C4—H4	112.1	C2—C15—H15B	110.9
C5—C4—H4	112.1	H15A—C15—H15B	108.9
C6—C4—H4	112.1	N2—C16—C15	105.95 (17)
N1—C5—C4	110.85 (14)	N2—C16—H16A	110.5
N1—C5—H5A	109.5	C15—C16—H16A	110.5
C4—C5—H5A	109.5	N2—C16—H16B	110.5
N1—C5—H5B	109.5	C15—C16—H16B	110.5
C4—C5—H5B	109.5	H16A—C16—H16B	108.7
H5A—C5—H5B	108.1	N2—C17—H17A	109.5
O2—C6—C10	112.31 (14)	N2—C17—H17B	109.5
O2—C6—C4	108.33 (14)	H17A—C17—H17B	109.5
C10—C6—C4	115.51 (15)	N2—C17—H17C	109.5
O2—C6—C7	112.10 (14)	H17A—C17—H17C	109.5
C10—C6—C7	104.91 (13)	H17B—C17—H17C	109.5
C4—C6—C7	103.35 (13)	N1—C18—H18A	109.5
N2—C7—C8	114.40 (14)	N1—C18—H18B	109.5
N2—C7—C2	102.91 (14)	H18A—C18—H18B	109.5
C8—C7—C2	117.03 (14)	N1—C18—H18C	109.5
N2—C7—C6	111.76 (13)	H18A—C18—H18C	109.5
C8—C7—C6	104.37 (14)	H18B—C18—H18C	109.5
C2—C7—C6	106.28 (13)	C3—N1—C18	113.60 (15)
O1—C8—C9	126.74 (16)	C3—N1—C5	113.99 (14)
O1—C8—C7	125.32 (17)	C18—N1—C5	114.19 (15)
C9—C8—C7	107.53 (13)	C7—N2—C17	116.69 (17)
C14—C9—C10	120.94 (17)	C7—N2—C16	107.45 (16)
C14—C9—C8	128.68 (16)	C17—N2—C16	114.03 (18)
C10—C9—C8	110.36 (14)	C6—O2—H2	109.5
C11—C10—C9	120.10 (17)

O3—C1—C2—C15	−22.8 (3)	C6—C7—C8—O1	−175.36 (16)
C4—C1—C2—C15	157.13 (17)	N2—C7—C8—C9	−110.88 (16)
O3—C1—C2—C3	107.2 (2)	C2—C7—C8—C9	128.67 (15)
C4—C1—C2—C3	−72.83 (18)	C6—C7—C8—C9	11.57 (17)
O3—C1—C2—C7	−138.5 (2)	O1—C8—C9—C14	−1.2 (3)
C4—C1—C2—C7	41.44 (18)	C7—C8—C9—C14	171.71 (17)
C1—C2—C3—N1	66.97 (17)	O1—C8—C9—C10	−179.96 (17)
C15—C2—C3—N1	−163.63 (15)	C7—C8—C9—C10	−7.01 (19)
C7—C2—C3—N1	−41.05 (18)	C14—C9—C10—C11	0.1 (3)
O3—C1—C4—C5	−112.9 (2)	C8—C9—C10—C11	178.94 (16)
C2—C1—C4—C5	67.20 (18)	C14—C9—C10—C6	−179.82 (16)
O3—C1—C4—C6	129.0 (2)	C8—C9—C10—C6	−1.0 (2)
C2—C1—C4—C6	−50.92 (17)	O2—C6—C10—C11	−49.6 (2)
C1—C4—C5—N1	−56.50 (19)	C4—C6—C10—C11	75.3 (2)
C6—C4—C5—N1	52.0 (2)	C7—C6—C10—C11	−171.64 (18)
C1—C4—C6—O2	−80.09 (16)	O2—C6—C10—C9	130.29 (15)
C5—C4—C6—O2	166.74 (14)	C4—C6—C10—C9	−104.79 (17)
C1—C4—C6—C10	152.95 (14)	C7—C6—C10—C9	8.28 (18)
C5—C4—C6—C10	39.8 (2)	C9—C10—C11—C12	−0.7 (3)
C1—C4—C6—C7	38.98 (16)	C6—C10—C11—C12	179.21 (17)
C5—C4—C6—C7	−74.19 (17)	C10—C11—C12—C13	1.1 (3)
C1—C2—C7—N2	102.34 (15)	C11—C12—C13—C14	−0.9 (3)
C15—C2—C7—N2	−19.57 (17)	C12—C13—C14—C9	0.3 (3)
C3—C2—C7—N2	−147.71 (14)	C10—C9—C14—C13	0.1 (3)
C1—C2—C7—C8	−131.31 (15)	C8—C9—C14—C13	−178.51 (17)
C15—C2—C7—C8	106.79 (17)	C1—C2—C15—C16	−113.14 (18)
C3—C2—C7—C8	−21.4 (2)	C3—C2—C15—C16	123.18 (18)
C1—C2—C7—C6	−15.26 (17)	C7—C2—C15—C16	−0.81 (19)
C15—C2—C7—C6	−137.16 (14)	C2—C15—C16—N2	21.1 (2)
C3—C2—C7—C6	94.70 (15)	C2—C3—N1—C18	168.67 (15)
O2—C6—C7—N2	−9.8 (2)	C2—C3—N1—C5	−58.18 (19)
C10—C6—C7—N2	112.33 (16)	C4—C5—N1—C3	53.1 (2)
C4—C6—C7—N2	−126.26 (15)	C4—C5—N1—C18	−174.04 (16)
O2—C6—C7—C8	−133.98 (15)	C8—C7—N2—C17	35.0 (2)
C10—C6—C7—C8	−11.83 (17)	C2—C7—N2—C17	163.01 (16)
C4—C6—C7—C8	109.58 (15)	C6—C7—N2—C17	−83.3 (2)
O2—C6—C7—C2	101.72 (16)	C8—C7—N2—C16	−94.49 (19)
C10—C6—C7—C2	−136.13 (14)	C2—C7—N2—C16	33.53 (18)
C4—C6—C7—C2	−14.72 (16)	C6—C7—N2—C16	147.18 (16)
N2—C7—C8—O1	62.2 (2)	C15—C16—N2—C7	−35.3 (2)
C2—C7—C8—O1	−58.3 (2)	C15—C16—N2—C17	−166.26 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2	0.82	2.12	2.655 (2)	123
C15—H15A···O3	0.97	2.56	2.974 (3)	106
C18—H18B···O3ⁱ	0.96	2.39	3.288 (3)	155

Symmetry code: (i) −x+1/2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₀N₂O₃
M_r	312.36
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	11.0862 (5), 11.6152 (5), 12.5670 (6)
β (°)	102.851 (9)
V (Å³)	1577.70 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.18 × 0.13 × 0.11

Data collection
Diffractometer	Nonius MACH-3 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.984, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	3226, 2764, 1978
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.120, 1.04
No. of reflections	2764
No. of parameters	211
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.18

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2	0.82	2.12	2.655 (2)	123
C15—H15A···O3	0.97	2.56	2.974 (3)	106
C18—H18B···O3ⁱ	0.96	2.39	3.288 (3)	155

Symmetry code: (i) −x+1/2, y+1/2, −z+3/2.

Acknowledgements

JS and SG thank the Management of The Madura College, Madurai, for their constant support.

References

Baluja, G., Municio, A. M. & Vega, S. (1964). Chem. Ind. pp. 2053–2054. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Dimmock, J. R., Arora, V. K., Wonko, S. L., Hamon, N. W., Quail, J. W., Jia, Z., Warrington, R. C., Fang, W. D. & Lee, J. S. (1990). Drug. Des. Deliv. 6, 183–194. CAS PubMed Google Scholar
Dimmock, J. R., Padmanilayam, M. P., Puthucode, R. N., Nazarali, A. J., Motaganahalli, N. L., Zello, G. A., Quail, J. W., Oloo, E. O., Kraatz, H. B., Prisciak, J. S., Allen, T. M., Santos, C. L., Balsarini, J., Clercq, E. D. & Manavathu, E. K. (2001). J. Med. Chem. 44, 586–593. Web of Science CSD CrossRef PubMed CAS Google Scholar
Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1996). XCAD4. University of Marburg, Germany. Google Scholar
Kaiser, E., Colescott, R. L., Bossinger, C. D. & Cook, P. I. (1970). Anal. Biochem. 34, 595–598. CrossRef CAS PubMed Web of Science Google Scholar
Mutus, B., Wagner, J. D., Talpas, C. J., Dimmock, J. R., Phillips, O. A. & Reid, R. S. (1989). Anal. Biochem. 177, 237–243. CrossRef CAS PubMed Web of Science Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 5| May 2009| Pages o1163-o1164

doi:10.1107/S1600536809015293

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

13-Hydr­­oxy-4,16-di­methyl-4,16-di­aza­penta­cyclo­[12.3.1.01,5.05,13.07,12]octa­deca-7(12),8,10-triene-6,18-dione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

13-Hydroxy-4,16-dimethyl-4,16-diazapentacyclo[12.3.1.0^1,5.0^5,13.0^7,12]octadeca-7(12),8,10-triene-6,18-dione