3,5a,9-Trimethyl-8-(2-phenylhydrazin-1-ylidene)-4,5,5a,9b-tetrahydro-3aH,8H-naphtho[1,2-b]furan-2(3H)-one

Yousuf, S.; Younas, S.M.; Ambreen, N.; Khan, K.M.; Miana, G.A.

doi:10.1107/S1600536812023847

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2112

https://doi.org/10.1107/S1600536812023847

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3,5a,9-Trimethyl-8-(2-phenylhydrazin-1-ylidene)-4,5,5a,9b-tetrahydro-3aH,8H-naphtho[1,2-b]furan-2(3H)-one

Sammer Yousuf,^a ^* Syed M. Younas,^b Nida Ambreen,^a Khalid M. Khan ^a and Ghulam A. Miana ^c

^aH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan, ^bDepartment of Chemistry, Allama Iqbal Open University, Islamabad, and ^cRiphah Institute of Pharmaceutical Sciences, Riphah International University, 7th Avenue G-7/4, Islamabad, Pakistan
^*Correspondence e-mail: dr.sammer.yousuf@gmail.com

(Received 12 May 2012; accepted 25 May 2012; online 16 June 2012)

The title compound, C₂₁H₂₄N₂O₂, is a phenyl hydrazine derivative of the well known anthelminthic agent α-santonin, which is composed of three fused rings (benzodieneone, cyclohexane and γ-lactone). The cyclohexadienone ring adopts a boat conformation, the cyclohexane ring is in a chair conformation and the trans-fused γ-lactone ring adopts a C-envelope conformation. In the crystal, molecules are linked by N—H⋯O and C—H⋯O hydrogen bonds, forming chains along the a axis.

Related literature

For the isolation of α-santonin, see: Kahler (1830 ). For the crystal structure and stereochemistry of α-santonin, see: White & Sim (1975 ); Coggon & Sim (1969 ). For puckering parameters, see: Cremer & Pople (1981 ).

Experimental

Crystal data

C₂₁H₂₄N₂O₂
M_r = 336.42
Orthorhombic, P 2₁ 2₁ 2₁
a = 10.5104 (12) Å
b = 11.5726 (14) Å
c = 15.4401 (18) Å
V = 1878.0 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 273 K
0.41 × 0.12 × 0.11 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.969, T_max = 0.992
11178 measured reflections
1999 independent reflections
1370 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.099
S = 1.04
1999 reflections
229 parameters
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.11 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1ⁱ	0.88	2.12	2.978 (4)	164
C8—H8A⋯O1ⁱ	0.93	2.43	3.290 (4)	153
Symmetry code: (i) x-1, y, z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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, PARST (Nardelli, 1995 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812023847/pv2547sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812023847/pv2547Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812023847/pv2547Isup3.cml

checkCIF report

Comment top

α-Santonin is an anthelminthic agent, first isolated by Kahler in 1830 from Artemisia santonica. The title compound is a derivative of α-santonin which was synthesized by reacting its dienone with phenyl hydrazine to study its biological activities.

The title molecule (Fig. 1) is composed of a phenyl hydrazine moeity (N1–N2/C1–C6) attached to the α-santonin which is composed of three fused rings. The cyclohexadienone ring (C7–C10/C17–C18) adopts a boat conformation C7 and C10 atoms 0.116 (3) and 0.140 (3) Å out of the plane formed by the remaining ring atoms (C8–C9/C17–C18). The cyclohexane ring (C10–C13/C16/C17) adopts a chair conformation with ring puckering parameters (Cremer & Pople, 1981): Q = 0.552 (3) Å, θ = 11.3 (3)° and φ = 171.3 (18)°. The trans fused γ lactone ring (O2/C13–C16 ) adopts a C13-envelope conformation with C13 0.614 (5) Å out of the plane formed by the rest of the ring atoms. The two methyl substituents on C10 and C14 exist in axial and pseudo equatorial orientations, respectively. In the crystal structure, the molecules are linked by N2–H2A···O1 and C8–H8A···O1 interactions to form infinite chains running along the a-axis (Fig. 2 and Tab. 1). The molecular dimensions in the title compound are similar to those found in structurally related compounds (White & Sim, 1975; Coggon & Sim, 1969). The stereochemistry was assigned on the basis of the published α-santonin crystal data (White & Sim, 1975; Coggon & Sim, 1969).

Related literature top

For the isolation of α-santonin, see: Kahler (1830). For the crystal structure and stereochemistry of α-santonin, see: White & Sim (1975); Coggon & Sim (1969). For puckering parameters, see: Cremer & Pople (1981).

Experimental top

In a 100 ml round bottomed-flask toluene (25 ml) and α-santonin (400 mg, 1.6 mmol) were taken and than added phenyl hydrazine (1.1 ml, 11.2 mmol) with contineous stirring. The reaction mixture was refluxed and monitored by TLC. After 24 h the reaction was completed, it was cooled and extracted with water. The organic phase was dried over anhydrous sodium sulfate, filtered and the solvent was evaporated under vacuum on a rotary evaporator. The crude product was chromatographed on a silica gel column using n-hexane:ethyl acetate (7:3) as an eluent to obtain pure yellow crystals of the title compound in 80% yield.

Structure description top

For the isolation of α-santonin, see: Kahler (1830). For the crystal structure and stereochemistry of α-santonin, see: White & Sim (1975); Coggon & Sim (1969). For puckering parameters, see: Cremer & Pople (1981).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 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), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. A view of the N—H···O and C—H···O hydrogen bonds (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity.

3,5a,9-Trimethyl-8-(2-phenylhydrazin-1-ylidene)-4,5,5a,9b- tetrahydro-3aH,8H-naphtho[1,2-b]furan-2(3H)-one top

Crystal data top

C₂₁H₂₄N₂O₂	F(000) = 720
M_r = 336.42	D_x = 1.190 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1104 reflections
a = 10.5104 (12) Å	θ = 2.2–18.1°
b = 11.5726 (14) Å	µ = 0.08 mm⁻¹
c = 15.4401 (18) Å	T = 273 K
V = 1878.0 (4) Å³	Block, yellow
Z = 4	0.41 × 0.12 × 0.11 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	1999 independent reflections
Radiation source: fine-focus sealed tube	1370 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
ω scan	θ_max = 25.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −12→11
T_min = 0.969, T_max = 0.992	k = −14→14
11178 measured reflections	l = −18→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.099	w = 1/[σ²(F_o²) + (0.0404P)² + 0.0789P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
1999 reflections	Δρ_max = 0.12 e Å⁻³
229 parameters	Δρ_min = −0.11 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1491 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0 (10)

Crystal data top

C₂₁H₂₄N₂O₂	V = 1878.0 (4) Å³
M_r = 336.42	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 10.5104 (12) Å	µ = 0.08 mm⁻¹
b = 11.5726 (14) Å	T = 273 K
c = 15.4401 (18) Å	0.41 × 0.12 × 0.11 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	1999 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1370 reflections with I > 2σ(I)
T_min = 0.969, T_max = 0.992	R_int = 0.056
11178 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.099	Δρ_max = 0.12 e Å⁻³
S = 1.04	Δρ_min = −0.11 e Å⁻³
1999 reflections	Absolute structure: Flack (1983), 1491 Friedel pairs
229 parameters	Absolute structure parameter: 0 (10)
0 restraints

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
O1	0.6908 (2)	0.2836 (2)	0.39485 (19)	0.0860 (9)
O2	0.4891 (2)	0.31375 (18)	0.35869 (14)	0.0599 (6)
N1	0.0266 (2)	0.4301 (2)	0.44717 (16)	0.0536 (7)
N2	−0.1011 (3)	0.4328 (2)	0.46280 (17)	0.0604 (8)
H2A	−0.1513	0.3781	0.4430	0.073*
C1	−0.2860 (3)	0.5333 (3)	0.5113 (2)	0.0641 (10)
H1B	−0.3359	0.4719	0.4925	0.077*
C2	−0.3417 (4)	0.6278 (4)	0.5491 (2)	0.0807 (12)
H2B	−0.4294	0.6290	0.5569	0.097*
C3	−0.2708 (5)	0.7203 (4)	0.5756 (3)	0.0867 (13)
H3A	−0.3099	0.7843	0.6006	0.104*
C4	−0.1405 (4)	0.7178 (3)	0.5648 (2)	0.0763 (11)
H4A	−0.0915	0.7804	0.5825	0.092*
C5	−0.0824 (4)	0.6230 (3)	0.52795 (19)	0.0615 (10)
H5A	0.0055	0.6219	0.5212	0.074*
C6	−0.1541 (3)	0.5297 (3)	0.50100 (19)	0.0525 (8)
C7	0.0722 (3)	0.3454 (3)	0.4016 (2)	0.0514 (8)
C8	−0.0011 (3)	0.2516 (3)	0.3661 (3)	0.0810 (12)
H8A	−0.0833	0.2388	0.3862	0.097*
C9	0.0463 (3)	0.1832 (4)	0.3053 (3)	0.0892 (14)
H9A	−0.0044	0.1232	0.2849	0.107*
C10	0.1765 (3)	0.1967 (3)	0.2675 (2)	0.0590 (9)
C11	0.2292 (3)	0.0739 (3)	0.2527 (2)	0.0661 (10)
H11A	0.2156	0.0288	0.3049	0.079*
H11B	0.1812	0.0377	0.2064	0.079*
C12	0.3705 (3)	0.0699 (3)	0.2297 (2)	0.0677 (10)
H12A	0.3996	−0.0096	0.2271	0.081*
H12B	0.3847	0.1055	0.1736	0.081*
C13	0.4414 (3)	0.1346 (3)	0.29870 (19)	0.0468 (8)
H13A	0.4208	0.0986	0.3544	0.056*
C14	0.5848 (3)	0.1514 (3)	0.2955 (2)	0.0528 (9)
H14A	0.6076	0.1756	0.2367	0.063*
C15	0.5995 (3)	0.2533 (3)	0.3539 (2)	0.0585 (9)
C16	0.3967 (3)	0.2589 (3)	0.30242 (19)	0.0485 (8)
H16A	0.4075	0.2919	0.2444	0.058*
C17	0.2590 (3)	0.2721 (3)	0.32667 (19)	0.0462 (8)
C18	0.2099 (3)	0.3460 (2)	0.3847 (2)	0.0489 (8)
C19	0.2862 (3)	0.4331 (3)	0.4352 (2)	0.0676 (10)
H19A	0.3618	0.4525	0.4036	0.101*
H19B	0.3092	0.4008	0.4903	0.101*
H19C	0.2361	0.5015	0.4440	0.101*
C20	0.1620 (4)	0.2591 (4)	0.1789 (2)	0.0962 (14)
H20A	0.1238	0.3335	0.1876	0.144*
H20B	0.1089	0.2137	0.1414	0.144*
H20C	0.2443	0.2685	0.1528	0.144*
C21	0.6686 (3)	0.0503 (3)	0.3200 (3)	0.0778 (11)
H21A	0.7553	0.0758	0.3243	0.117*
H21B	0.6622	−0.0086	0.2764	0.117*
H21C	0.6416	0.0196	0.3747	0.117*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0446 (16)	0.0785 (18)	0.135 (2)	−0.0044 (14)	−0.0081 (16)	−0.0317 (17)
O2	0.0391 (13)	0.0468 (12)	0.0939 (16)	−0.0028 (11)	0.0040 (13)	−0.0164 (12)
N1	0.0413 (17)	0.0588 (16)	0.0606 (16)	0.0050 (14)	0.0022 (14)	−0.0076 (15)
N2	0.0418 (17)	0.0653 (18)	0.0742 (19)	0.0057 (15)	0.0050 (15)	−0.0194 (16)
C1	0.054 (2)	0.071 (2)	0.067 (2)	0.0120 (19)	0.0064 (19)	−0.007 (2)
C2	0.065 (3)	0.094 (3)	0.083 (3)	0.022 (2)	0.011 (2)	−0.013 (3)
C3	0.094 (4)	0.082 (3)	0.084 (3)	0.030 (3)	0.007 (3)	−0.022 (2)
C4	0.090 (3)	0.073 (3)	0.065 (2)	0.009 (2)	−0.004 (2)	−0.018 (2)
C5	0.066 (3)	0.068 (2)	0.051 (2)	0.008 (2)	−0.0021 (18)	−0.0071 (18)
C6	0.053 (2)	0.061 (2)	0.0441 (18)	0.0110 (18)	0.0035 (17)	−0.0011 (17)
C7	0.040 (2)	0.052 (2)	0.062 (2)	0.0034 (15)	0.0010 (16)	−0.0070 (18)
C8	0.037 (2)	0.078 (3)	0.128 (3)	−0.003 (2)	0.009 (2)	−0.039 (3)
C9	0.042 (2)	0.088 (3)	0.138 (4)	−0.009 (2)	0.000 (2)	−0.055 (3)
C10	0.050 (2)	0.061 (2)	0.066 (2)	0.0008 (18)	−0.0068 (18)	−0.0180 (18)
C11	0.056 (2)	0.067 (2)	0.075 (2)	−0.0019 (19)	−0.0070 (19)	−0.0314 (19)
C12	0.064 (3)	0.067 (2)	0.073 (2)	0.0121 (19)	−0.005 (2)	−0.027 (2)
C13	0.046 (2)	0.0500 (18)	0.0440 (17)	0.0033 (14)	0.0070 (16)	−0.0049 (16)
C14	0.044 (2)	0.057 (2)	0.0566 (19)	0.0050 (16)	0.0108 (17)	−0.0030 (17)
C15	0.038 (2)	0.054 (2)	0.084 (2)	−0.0033 (18)	0.0100 (19)	−0.006 (2)
C16	0.0470 (19)	0.0466 (18)	0.0518 (17)	0.0021 (15)	0.0030 (16)	0.0021 (17)
C17	0.0387 (19)	0.0442 (18)	0.0557 (18)	−0.0011 (14)	−0.0006 (15)	−0.0051 (16)
C18	0.043 (2)	0.0490 (19)	0.0546 (19)	0.0014 (16)	−0.0012 (16)	−0.0066 (16)
C19	0.049 (2)	0.069 (2)	0.085 (2)	0.0004 (19)	0.004 (2)	−0.030 (2)
C20	0.103 (3)	0.100 (3)	0.085 (3)	0.018 (3)	−0.043 (3)	−0.016 (3)
C21	0.065 (2)	0.063 (2)	0.105 (3)	0.014 (2)	−0.007 (2)	−0.020 (2)

Geometric parameters (Å, º) top

O1—C15	1.202 (4)	C10—C20	1.554 (5)
O2—C15	1.357 (4)	C11—C12	1.528 (4)
O2—C16	1.449 (4)	C11—H11A	0.9700
N1—C7	1.298 (4)	C11—H11B	0.9700
N1—N2	1.365 (3)	C12—C13	1.501 (4)
N2—C6	1.385 (4)	C12—H12A	0.9700
N2—H2A	0.8779	C12—H12B	0.9700
C1—C2	1.371 (4)	C13—C16	1.515 (4)
C1—C6	1.396 (4)	C13—C14	1.520 (4)
C1—H1B	0.9300	C13—H13A	0.9800
C2—C3	1.367 (6)	C14—C15	1.492 (4)
C2—H2B	0.9300	C14—C21	1.513 (4)
C3—C4	1.380 (5)	C14—H14A	0.9800
C3—H3A	0.9300	C16—C17	1.502 (4)
C4—C5	1.378 (5)	C16—H16A	0.9800
C4—H4A	0.9300	C17—C18	1.341 (4)
C5—C6	1.381 (5)	C18—C19	1.506 (4)
C5—H5A	0.9300	C19—H19A	0.9600
C7—C8	1.440 (4)	C19—H19B	0.9600
C7—C18	1.471 (4)	C19—H19C	0.9600
C8—C9	1.325 (5)	C20—H20A	0.9600
C8—H8A	0.9300	C20—H20B	0.9600
C9—C10	1.495 (5)	C20—H20C	0.9600
C9—H9A	0.9300	C21—H21A	0.9600
C10—C17	1.533 (4)	C21—H21B	0.9600
C10—C11	1.542 (5)	C21—H21C	0.9600

C15—O2—C16	108.3 (2)	C11—C12—H12B	110.2
C7—N1—N2	118.4 (3)	H12A—C12—H12B	108.5
N1—N2—C6	119.3 (3)	C12—C13—C16	110.3 (3)
N1—N2—H2A	120.9	C12—C13—C14	122.2 (3)
C6—N2—H2A	119.4	C16—C13—C14	100.8 (2)
C2—C1—C6	119.8 (4)	C12—C13—H13A	107.6
C2—C1—H1B	120.1	C16—C13—H13A	107.6
C6—C1—H1B	120.1	C14—C13—H13A	107.6
C3—C2—C1	121.3 (4)	C15—C14—C21	113.5 (3)
C3—C2—H2B	119.4	C15—C14—C13	100.6 (3)
C1—C2—H2B	119.4	C21—C14—C13	118.1 (3)
C2—C3—C4	119.2 (4)	C15—C14—H14A	108.0
C2—C3—H3A	120.4	C21—C14—H14A	108.0
C4—C3—H3A	120.4	C13—C14—H14A	108.0
C5—C4—C3	120.5 (4)	O1—C15—O2	120.2 (3)
C5—C4—H4A	119.8	O1—C15—C14	129.2 (3)
C3—C4—H4A	119.8	O2—C15—C14	110.6 (3)
C4—C5—C6	120.3 (4)	O2—C16—C17	116.9 (2)
C4—C5—H5A	119.8	O2—C16—C13	103.3 (2)
C6—C5—H5A	119.8	C17—C16—C13	113.9 (3)
C5—C6—N2	122.9 (3)	O2—C16—H16A	107.4
C5—C6—C1	119.0 (3)	C17—C16—H16A	107.4
N2—C6—C1	118.1 (3)	C13—C16—H16A	107.4
N1—C7—C8	125.3 (3)	C18—C17—C16	127.0 (3)
N1—C7—C18	117.1 (3)	C18—C17—C10	122.9 (3)
C8—C7—C18	117.6 (3)	C16—C17—C10	109.8 (3)
C9—C8—C7	121.2 (3)	C17—C18—C7	119.6 (3)
C9—C8—H8A	119.4	C17—C18—C19	124.6 (3)
C7—C8—H8A	119.4	C7—C18—C19	115.8 (3)
C8—C9—C10	123.9 (4)	C18—C19—H19A	109.5
C8—C9—H9A	118.0	C18—C19—H19B	109.5
C10—C9—H9A	118.0	H19A—C19—H19B	109.5
C9—C10—C17	110.2 (3)	C18—C19—H19C	109.5
C9—C10—C11	106.8 (3)	H19A—C19—H19C	109.5
C17—C10—C11	114.2 (3)	H19B—C19—H19C	109.5
C9—C10—C20	107.6 (3)	C10—C20—H20A	109.5
C17—C10—C20	108.4 (3)	C10—C20—H20B	109.5
C11—C10—C20	109.4 (3)	H20A—C20—H20B	109.5
C12—C11—C10	114.3 (3)	C10—C20—H20C	109.5
C12—C11—H11A	108.7	H20A—C20—H20C	109.5
C10—C11—H11A	108.7	H20B—C20—H20C	109.5
C12—C11—H11B	108.7	C14—C21—H21A	109.5
C10—C11—H11B	108.7	C14—C21—H21B	109.5
H11A—C11—H11B	107.6	H21A—C21—H21B	109.5
C13—C12—C11	107.6 (3)	C14—C21—H21C	109.5
C13—C12—H12A	110.2	H21A—C21—H21C	109.5
C11—C12—H12A	110.2	H21B—C21—H21C	109.5
C13—C12—H12B	110.2

C7—N1—N2—C6	−171.3 (3)	C16—O2—C15—C14	−1.8 (3)
C6—C1—C2—C3	1.4 (6)	C21—C14—C15—O1	28.7 (5)
C1—C2—C3—C4	−0.7 (6)	C13—C14—C15—O1	155.9 (4)
C2—C3—C4—C5	−0.1 (6)	C21—C14—C15—O2	−150.0 (3)
C3—C4—C5—C6	0.3 (5)	C13—C14—C15—O2	−22.8 (3)
C4—C5—C6—N2	179.3 (3)	C15—O2—C16—C17	151.9 (3)
C4—C5—C6—C1	0.3 (5)	C15—O2—C16—C13	26.1 (3)
N1—N2—C6—C5	−3.0 (5)	C12—C13—C16—O2	−169.4 (2)
N1—N2—C6—C1	176.0 (3)	C14—C13—C16—O2	−38.9 (3)
C2—C1—C6—C5	−1.2 (5)	C12—C13—C16—C17	62.9 (3)
C2—C1—C6—N2	179.8 (3)	C14—C13—C16—C17	−166.7 (3)
N2—N1—C7—C8	−0.7 (5)	O2—C16—C17—C18	13.5 (5)
N2—N1—C7—C18	179.0 (3)	C13—C16—C17—C18	133.9 (3)
N1—C7—C8—C9	165.1 (4)	O2—C16—C17—C10	−172.9 (2)
C18—C7—C8—C9	−14.7 (5)	C13—C16—C17—C10	−52.4 (3)
C7—C8—C9—C10	−0.8 (7)	C9—C10—C17—C18	−21.6 (5)
C8—C9—C10—C17	17.8 (6)	C11—C10—C17—C18	−141.8 (3)
C8—C9—C10—C11	142.3 (4)	C20—C10—C17—C18	95.9 (4)
C8—C9—C10—C20	−100.2 (5)	C9—C10—C17—C16	164.4 (3)
C9—C10—C11—C12	−169.5 (3)	C11—C10—C17—C16	44.3 (4)
C17—C10—C11—C12	−47.5 (4)	C20—C10—C17—C16	−78.0 (3)
C20—C10—C11—C12	74.3 (4)	C16—C17—C18—C7	−178.8 (3)
C10—C11—C12—C13	54.0 (4)	C10—C17—C18—C7	8.3 (5)
C11—C12—C13—C16	−60.2 (4)	C16—C17—C18—C19	1.7 (5)
C11—C12—C13—C14	−178.2 (3)	C10—C17—C18—C19	−171.2 (3)
C12—C13—C14—C15	159.0 (3)	N1—C7—C18—C17	−169.1 (3)
C16—C13—C14—C15	36.5 (3)	C8—C7—C18—C17	10.7 (5)
C12—C13—C14—C21	−76.9 (4)	N1—C7—C18—C19	10.4 (4)
C16—C13—C14—C21	160.6 (3)	C8—C7—C18—C19	−169.8 (3)
C16—O2—C15—O1	179.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.88	2.12	2.978 (4)	164
C8—H8A···O1ⁱ	0.93	2.43	3.290 (4)	153

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₄N₂O₂
M_r	336.42
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	273
a, b, c (Å)	10.5104 (12), 11.5726 (14), 15.4401 (18)
V (Å³)	1878.0 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.41 × 0.12 × 0.11

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.969, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	11178, 1999, 1370
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.099, 1.04
No. of reflections	1999
No. of parameters	229
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.11
Absolute structure	Flack (1983), 1491 Friedel pairs
Absolute structure parameter	0 (10)

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.8800	2.1200	2.978 (4)	164.00
C8—H8A···O1ⁱ	0.9300	2.4300	3.290 (4)	153.00

Symmetry code: (i) x−1, y, z.

Acknowledgements

The authors gratefully acknowledge the Pakistan Academy of Sciences for funding project reference No. 5–9/PAS/1335 entitled "Biology-Oriented Syntheses (BIOS) Based Synthesis of Libraries of Santonin".

References

Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Coggon, P. & Sim, G. A. (1969). J. Chem. Soc. B., pp. 237–242. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Kahler, M. (1830). Arch. Pharm. 34, 318. CrossRef Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals 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
White, D. N. J. & Sim, G. A. (1975). J. Chem. Soc. Perkin Trans 2., pp. 1826–1831. CrossRef Google Scholar

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

3,5a,9-Tri­methyl-8-(2-phenylhydrazin-1-yl­idene)-4,5,5a,9b-tetra­hydro-3aH,8H-naphtho[1,2-b]furan-2(3H)-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3,5a,9-Trimethyl-8-(2-phenylhydrazin-1-ylidene)-4,5,5a,9b-tetrahydro-3aH,8H-naphtho[1,2-b]furan-2(3H)-one