2-(4-Methyl­cyclo­hex-3-en­yl)propan-2-yl N-phenyl­carbamate

Ghalib, R.M.; Sulaiman, O.; Mehdi, S.H.; Goh, J.H.; Fun, H.-K.

doi:10.1107/S1600536810025080

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 8| August 2010| Pages o1889-o1890

https://doi.org/10.1107/S1600536810025080

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2-(4-Methylcyclohex-3-enyl)propan-2-yl N-phenylcarbamate

Raza Murad Ghalib,^a Othman Sulaiman,^a Sayed Hasan Mehdi,^a Jia Hao Goh ^b ‡ and Hoong-Kun Fun ^b ^*§

^aSchool of Industrial Technology, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 25 June 2010; accepted 25 June 2010; online 3 July 2010)

In the title carbamate compound, C₁₇H₂₃NO₂, one of the Csp³ atoms of the cyclohexene ring is disordered over two sites with refined occupancies of 0.55 (2) and 0.45 (2), both disorder components resulting in half-boat conformations. The mean plane through the carbamate unit is inclined at interplanar angles of 14.80 (13), 18.30 (17) and 24.0 (2)°, respectively, with respect to the phenyl ring, and the major and minor disorder component cyclohexene rings. In the crystal structure, adjacent molecules are linked into chains along [001] via intermolecular N—H⋯O hydrogen bonds. The crystal structure is further stabilized by weak intermolecular C—H⋯π interactions.

Related literature

For general background to and applications of the title compound, see: Banerjee et al. (1978 ); Graia et al. (2009 ); Ibuka et al. (1985 ); Lapidus et al. (1987 ); Loev & Kormendy (1963 ); Muradov et al. (1986 ); Niu et al. (2007 ); Ibuka et al. (1985). For related carbamate structures, see: Garden et al. (2007 ); Graia et al. (2009). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₇H₂₃NO₂
M_r = 273.36
Monoclinic, C c
a = 19.3067 (19) Å
b = 9.0058 (9) Å
c = 8.9521 (9) Å
β = 100.964 (3)°
V = 1528.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.58 × 0.20 × 0.10 mm

Data collection

Bruker APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.957, T_max = 0.992
8744 measured reflections
2205 independent reflections
2053 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.154
S = 1.15
2205 reflections
187 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.76 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O2ⁱ	0.86	2.12	2.969 (3)	170
C13—H13A⋯Cg1ⁱⁱ	0.97	2.62	3.566 (3)	166
Symmetry codes: (i) $[x, -y+2, z-{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810025080/hb5524sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810025080/hb5524Isup2.hkl

checkCIF report

Comment top

Carbamates are well-known class of compounds with biological activity (Muradov et al., 1986). They can be prepared by different methods, for example by nickel-catalyzed coupling of CO₂ and amines (Niu et al., 2007), by stirring of alcohols including steroids as well as primary and secondary alcohols, polyols, phenols with sodium cynate, and trifluoroacetic acid (Loev & Kormendy, 1963), by carbonylation of aromatic nitro compounds (Lapidus et al., 1987), by the reaction of isocynates with alcohols (Ibuka et al., 1985) in the presence of lewis acid and by the reaction of an amine and an alcohol with phosgene. Phytosterol, β-Sitosterol, stigmasterol and cholesterol react with phenyl isocyanate to give carbamate (Banerjee et al., 1978; Graia et al., 2009). In this study the title compound has been synthesized by the reaction of α-terpineol with phenylisocyanate in the presence of catalytic amount of HCl in chloroform solvent.

In the title carbamate compound (Fig. 1), atom C10 of the cyclohexene ring (C9-C14) is disordered over two sites with a refined occupancy ratio of 0.55 (2):0.45 (2). The major (C9/C10A/C11-C14) and minor (C9/C10B/C11-C14) disordered cyclohexene rings adopt the same conformation, that is the half-boat conformation; puckering parameters Q = 0.427 (4) Å, θ = 57.4 (5)°, φ = 335.9 (7)° for major disordered component and Q = 0.651 (6) Å, θ = 131.6 (4)° and φ = 161.7 (7)° for minor disordered component. The mean plane through the carbamate moiety (N1/C7/O1/O2) is inclined at interplanar angles of 14.80 (13), 18.30 (17) and 24.0 (2)°, respectively, with respect to the C1-C6 phenyl ring, major and minor disordered cyclohexene rings. The bond lengths and angles are comparable to those related carbamate structures (Garden et al., 2007; Graia et al., 2009).

In the crystal structure, intermolecular N1—H1N1···O2 hydrogen bonds (Table 1) link adjacent molecules into one-dimensional chains running along the [001] direction (Fig. 2). Further stabilization of the crystal structure is provided by weak intermolecular C13—H13A···Cg1 interactions (Table 1) involving the centroid of the C1-C6 phenyl ring.

Related literature top

For general background to and applications of the title compound, see: Banerjee et al. (1978); Graia et al. (2009); Ibuka et al. (1985); Lapidus et al. (1987); Loev & Kormendy (1963); Muradov et al. (1986); Niu et al. (2007); Ibuka et al. (1985). For related carbamate structures, see: Garden et al. (2007); Graia et al. (2009). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of α-terpineol (1.640 ml) and phenylisocyanate (1.087 ml) in 1:1 molar ratio were stirred in chloroform for 30 minutes in the presence of catalytic amount of HCl. The reaction mixture was dried on rota vapor at low pressure and then chromatographed over silica gel column loaded in light petroleum ether. The column was eluted only with light petroleum ether to give five fractions of the title compound. These fractions were mixed together on the basis of same TLC results and crystallized with chloroform:alcohol (1:1) to give the colourless needles of (I) (1.93 g, M.p. 378 K). The melting point was taken on Thermo Fisher digital melting point apparatus of IA9000 series and is uncorrected. Open column chromatography was performed on silica gel 60 (Merck, 0.040–0.063 mm, 230–400 mesh ASTM) and Sephadex LH-20 (Pharmacia). TLCs were taken on silica gel plates (silica gel 60 F₂₅₄ on aluminum foil, Merck).

Structure description top

For general background to and applications of the title compound, see: Banerjee et al. (1978); Graia et al. (2009); Ibuka et al. (1985); Lapidus et al. (1987); Loev & Kormendy (1963); Muradov et al. (1986); Niu et al. (2007); Ibuka et al. (1985). For related carbamate structures, see: Garden et al. (2007); Graia et al. (2009). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I), showing 30 % probability displacement ellipsoids. Open bonds indicate the minor disordered component.
	Fig. 2. The crystal structure of (I), viewed down the b axis, showing molecules being linked into one-dimensional chains along the c axis. Minor disordered component and H atoms not involved in intermolecular hydrogen bonds (dashed lines) have been omitted for clarity.

2-(4-Methylcyclohex-3-enyl)propan-2-yl N-phenylcarbamate top

Crystal data top

C₁₇H₂₃NO₂	F(000) = 592
M_r = 273.36	D_x = 1.188 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 2414 reflections
a = 19.3067 (19) Å	θ = 3.3–32.4°
b = 9.0058 (9) Å	µ = 0.08 mm⁻¹
c = 8.9521 (9) Å	T = 100 K
β = 100.964 (3)°	Needle, colourless
V = 1528.1 (3) Å³	0.58 × 0.20 × 0.10 mm
Z = 4

Data collection top

Bruker APEXII DUO CCD diffractometer	2205 independent reflections
Radiation source: fine-focus sealed tube	2053 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
φ and ω scans	θ_max = 30.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −26→27
T_min = 0.957, T_max = 0.992	k = −12→11
8744 measured reflections	l = −12→12

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)] = 0.050	H-atom parameters constrained
wR(F²) = 0.154	w = 1/[σ²(F_o²) + (0.0981P)² + 0.223P] where P = (F_o² + 2F_c²)/3
S = 1.15	(Δ/σ)_max < 0.001
2205 reflections	Δρ_max = 0.68 e Å⁻³
187 parameters	Δρ_min = −0.76 e Å⁻³
4 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.044 (6)

Crystal data top

C₁₇H₂₃NO₂	V = 1528.1 (3) Å³
M_r = 273.36	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 19.3067 (19) Å	µ = 0.08 mm⁻¹
b = 9.0058 (9) Å	T = 100 K
c = 8.9521 (9) Å	0.58 × 0.20 × 0.10 mm
β = 100.964 (3)°

Data collection top

Bruker APEXII DUO CCD diffractometer	2205 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2053 reflections with I > 2σ(I)
T_min = 0.957, T_max = 0.992	R_int = 0.049
8744 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	4 restraints
wR(F²) = 0.154	H-atom parameters constrained
S = 1.15	Δρ_max = 0.68 e Å⁻³
2205 reflections	Δρ_min = −0.76 e Å⁻³
187 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
O1	0.15396 (9)	0.88990 (19)	0.87624 (19)	0.0181 (4)
O2	0.08897 (11)	0.8780 (2)	1.0641 (2)	0.0208 (4)
N1	0.07470 (11)	1.0610 (2)	0.8828 (2)	0.0164 (4)
H1N1	0.0841	1.0796	0.7946	0.020*
C1	−0.00477 (14)	1.1337 (3)	1.0559 (3)	0.0212 (5)
H1A	−0.0006	1.0410	1.1025	0.025*
C2	−0.04625 (16)	1.2429 (3)	1.1041 (3)	0.0272 (6)
H2A	−0.0697	1.2221	1.1834	0.033*
C3	−0.05361 (16)	1.3820 (3)	1.0371 (4)	0.0286 (6)
H3A	−0.0810	1.4547	1.0716	0.034*
C4	−0.01903 (15)	1.4106 (3)	0.9166 (3)	0.0264 (6)
H4A	−0.0244	1.5025	0.8684	0.032*
C5	0.02310 (14)	1.3035 (3)	0.8685 (3)	0.0224 (5)
H5A	0.0467	1.3246	0.7897	0.027*
C6	0.03042 (11)	1.1636 (3)	0.9376 (3)	0.0155 (4)
C7	0.10429 (12)	0.9363 (3)	0.9525 (3)	0.0165 (4)
C8	0.19360 (13)	0.7514 (3)	0.9145 (3)	0.0180 (5)
C9	0.24506 (13)	0.7554 (3)	0.8015 (3)	0.0161 (4)
H9A	0.2783	0.8351	0.8398	0.019*	0.55 (2)
H9B	0.2736	0.8434	0.8163	0.019*	0.45 (2)
C10A	0.2126 (3)	0.8036 (10)	0.6393 (5)	0.0169 (17)	0.55 (2)
H10A	0.1711	0.7435	0.6029	0.020*	0.55 (2)
H10B	0.1974	0.9062	0.6412	0.020*	0.55 (2)
C10B	0.2058 (3)	0.7435 (16)	0.6365 (7)	0.025 (2)*	0.45 (2)
H10C	0.1653	0.8094	0.6189	0.030*	0.45 (2)
H10D	0.1895	0.6426	0.6136	0.030*	0.45 (2)
C11	0.26080 (18)	0.7903 (4)	0.5329 (3)	0.0338 (7)
H11A	0.2476	0.8317	0.4365	0.041*	0.55 (2)
H11B	0.2506	0.8616	0.4521	0.041*	0.45 (2)
C12	0.32574 (14)	0.7183 (3)	0.5690 (3)	0.0205 (5)
C13	0.34562 (13)	0.6355 (3)	0.7083 (3)	0.0227 (5)
H13A	0.3867	0.6828	0.7687	0.027*
H13B	0.3598	0.5369	0.6825	0.027*
C14	0.2908 (2)	0.6188 (4)	0.8067 (4)	0.0392 (9)
H14A	0.3141	0.6005	0.9110	0.047*
H14B	0.2612	0.5336	0.7724	0.047*
C15	0.14268 (18)	0.6215 (3)	0.8893 (5)	0.0355 (7)
H15A	0.1125	0.6249	0.9629	0.053*
H15B	0.1688	0.5301	0.9002	0.053*
H15C	0.1146	0.6272	0.7887	0.053*
C16	0.23442 (17)	0.7591 (4)	1.0772 (3)	0.0316 (7)
H16A	0.2020	0.7563	1.1463	0.047*
H16B	0.2610	0.8497	1.0915	0.047*
H16C	0.2660	0.6760	1.0966	0.047*
C17	0.37752 (17)	0.7262 (3)	0.4634 (3)	0.0271 (5)
H17A	0.3578	0.7843	0.3757	0.041*
H17B	0.3874	0.6278	0.4321	0.041*
H17C	0.4204	0.7716	0.5151	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0224 (8)	0.0176 (8)	0.0163 (8)	0.0042 (6)	0.0091 (6)	0.0011 (6)
O2	0.0282 (9)	0.0201 (9)	0.0167 (8)	0.0026 (7)	0.0113 (7)	0.0013 (6)
N1	0.0198 (9)	0.0193 (10)	0.0116 (8)	0.0022 (7)	0.0069 (7)	−0.0003 (7)
C1	0.0232 (11)	0.0244 (13)	0.0184 (11)	0.0048 (9)	0.0095 (9)	0.0040 (9)
C2	0.0319 (14)	0.0304 (15)	0.0241 (12)	0.0080 (10)	0.0172 (11)	0.0051 (10)
C3	0.0343 (14)	0.0255 (14)	0.0302 (14)	0.0102 (11)	0.0166 (12)	0.0004 (10)
C4	0.0309 (13)	0.0208 (12)	0.0306 (14)	0.0034 (10)	0.0137 (11)	0.0018 (10)
C5	0.0237 (11)	0.0207 (13)	0.0258 (12)	0.0019 (9)	0.0126 (9)	0.0028 (9)
C6	0.0141 (9)	0.0177 (11)	0.0152 (9)	−0.0004 (8)	0.0042 (7)	−0.0019 (8)
C7	0.0176 (10)	0.0186 (11)	0.0140 (10)	−0.0009 (8)	0.0051 (8)	−0.0041 (8)
C8	0.0220 (11)	0.0145 (11)	0.0191 (11)	0.0041 (8)	0.0081 (8)	0.0015 (8)
C9	0.0184 (9)	0.0163 (11)	0.0147 (10)	0.0013 (8)	0.0057 (8)	−0.0006 (8)
C10A	0.020 (2)	0.018 (4)	0.014 (2)	0.0052 (19)	0.0056 (14)	0.0028 (15)
C11	0.0466 (17)	0.0417 (17)	0.0160 (12)	0.0201 (14)	0.0135 (12)	0.0090 (11)
C12	0.0223 (11)	0.0227 (12)	0.0180 (10)	0.0001 (9)	0.0079 (9)	−0.0042 (9)
C13	0.0210 (11)	0.0260 (13)	0.0227 (12)	0.0058 (9)	0.0079 (9)	−0.0001 (9)
C14	0.0482 (17)	0.0328 (16)	0.0466 (19)	0.0244 (14)	0.0343 (16)	0.0214 (14)
C15	0.0387 (15)	0.0185 (13)	0.057 (2)	−0.0059 (11)	0.0284 (15)	−0.0076 (12)
C16	0.0340 (14)	0.0489 (18)	0.0134 (11)	0.0186 (13)	0.0082 (10)	0.0086 (11)
C17	0.0346 (13)	0.0235 (13)	0.0273 (13)	−0.0006 (10)	0.0163 (11)	−0.0031 (10)

Geometric parameters (Å, º) top

O1—C7	1.345 (3)	C10A—C11	1.458 (5)
O1—C8	1.470 (3)	C10A—H10A	0.9700
O2—C7	1.214 (3)	C10A—H10B	0.9700
N1—C7	1.356 (3)	C10B—C11	1.594 (7)
N1—C6	1.409 (3)	C10B—H10C	0.9700
N1—H1N1	0.8600	C10B—H10D	0.9700
C1—C2	1.388 (4)	C11—C12	1.393 (4)
C1—C6	1.389 (3)	C11—H11A	0.9300
C1—H1A	0.9300	C11—H11B	0.9600
C2—C3	1.385 (4)	C12—C13	1.441 (4)
C2—H2A	0.9300	C12—C17	1.502 (3)
C3—C4	1.396 (4)	C13—C14	1.509 (4)
C3—H3A	0.9300	C13—H13A	0.9700
C4—C5	1.383 (4)	C13—H13B	0.9700
C4—H4A	0.9300	C14—H14A	0.9700
C5—C6	1.399 (4)	C14—H14B	0.9700
C5—H5A	0.9300	C15—H15A	0.9600
C8—C15	1.517 (4)	C15—H15B	0.9600
C8—C16	1.520 (4)	C15—H15C	0.9600
C8—C9	1.547 (3)	C16—H16A	0.9600
C9—C14	1.510 (4)	C16—H16B	0.9600
C9—C10B	1.531 (6)	C16—H16C	0.9600
C9—C10A	1.531 (5)	C17—H17A	0.9600
C9—H9A	0.9800	C17—H17B	0.9600
C9—H9B	0.9600	C17—H17C	0.9600

C7—O1—C8	122.38 (19)	H10A—C10A—H10B	107.7
C7—N1—C6	127.81 (19)	C9—C10B—C11	106.2 (5)
C7—N1—H1N1	116.1	C9—C10B—H10C	110.5
C6—N1—H1N1	116.1	C11—C10B—H10C	110.5
C2—C1—C6	119.6 (2)	C9—C10B—H10D	110.5
C2—C1—H1A	120.2	C11—C10B—H10D	110.5
C6—C1—H1A	120.2	H10C—C10B—H10D	108.7
C3—C2—C1	121.6 (3)	C12—C11—C10A	123.1 (3)
C3—C2—H2A	119.2	C12—C11—C10B	114.4 (4)
C1—C2—H2A	119.2	C12—C11—H11A	118.5
C2—C3—C4	118.5 (3)	C10A—C11—H11A	118.5
C2—C3—H3A	120.8	C10B—C11—H11A	123.4
C4—C3—H3A	120.8	C12—C11—H11B	122.2
C5—C4—C3	120.5 (3)	C10A—C11—H11B	111.8
C5—C4—H4A	119.7	C10B—C11—H11B	123.4
C3—C4—H4A	119.7	C11—C12—C13	121.4 (2)
C4—C5—C6	120.4 (2)	C11—C12—C17	120.6 (2)
C4—C5—H5A	119.8	C13—C12—C17	118.0 (2)
C6—C5—H5A	119.8	C12—C13—C14	117.1 (2)
C1—C6—C5	119.3 (2)	C12—C13—H13A	108.0
C1—C6—N1	123.8 (2)	C14—C13—H13A	108.0
C5—C6—N1	117.0 (2)	C12—C13—H13B	108.0
O2—C7—O1	126.3 (2)	C14—C13—H13B	108.0
O2—C7—N1	126.1 (2)	H13A—C13—H13B	107.3
O1—C7—N1	107.62 (19)	C13—C14—C9	111.8 (2)
O1—C8—C15	109.0 (2)	C13—C14—H14A	109.3
O1—C8—C16	109.7 (2)	C9—C14—H14A	109.3
C15—C8—C16	112.4 (3)	C13—C14—H14B	109.3
O1—C8—C9	101.42 (18)	C9—C14—H14B	109.3
C15—C8—C9	113.5 (2)	H14A—C14—H14B	107.9
C16—C8—C9	110.2 (2)	C8—C15—H15A	109.5
C14—C9—C10B	98.7 (5)	C8—C15—H15B	109.5
C14—C9—C10A	113.1 (3)	H15A—C15—H15B	109.5
C14—C9—C8	113.9 (2)	C8—C15—H15C	109.5
C10B—C9—C8	111.6 (3)	H15A—C15—H15C	109.5
C10A—C9—C8	115.4 (2)	H15B—C15—H15C	109.5
C14—C9—H9A	104.3	C8—C16—H16A	109.5
C10B—C9—H9A	124.1	C8—C16—H16B	109.5
C10A—C9—H9A	104.3	H16A—C16—H16B	109.5
C8—C9—H9A	104.3	C8—C16—H16C	109.5
C14—C9—H9B	110.6	H16A—C16—H16C	109.5
C10B—C9—H9B	111.0	H16B—C16—H16C	109.5
C10A—C9—H9B	91.0	C12—C17—H17A	109.5
C8—C9—H9B	110.7	C12—C17—H17B	109.5
C11—C10A—C9	113.5 (3)	H17A—C17—H17B	109.5
C11—C10A—H10A	108.9	C12—C17—H17C	109.5
C9—C10A—H10A	108.9	H17A—C17—H17C	109.5
C11—C10A—H10B	108.9	H17B—C17—H17C	109.5
C9—C10A—H10B	108.9

C6—C1—C2—C3	0.0 (5)	O1—C8—C9—C10A	−43.0 (5)
C1—C2—C3—C4	1.0 (5)	C15—C8—C9—C10A	73.8 (5)
C2—C3—C4—C5	−1.7 (5)	C16—C8—C9—C10A	−159.1 (4)
C3—C4—C5—C6	1.4 (5)	C14—C9—C10A—C11	−40.1 (8)
C2—C1—C6—C5	−0.3 (4)	C10B—C9—C10A—C11	−89.5 (9)
C2—C1—C6—N1	178.8 (2)	C8—C9—C10A—C11	−173.6 (5)
C4—C5—C6—C1	−0.4 (4)	C14—C9—C10B—C11	−74.1 (7)
C4—C5—C6—N1	−179.5 (2)	C10A—C9—C10B—C11	60.9 (8)
C7—N1—C6—C1	−17.3 (4)	C8—C9—C10B—C11	165.8 (5)
C7—N1—C6—C5	161.8 (2)	C9—C10A—C11—C12	9.9 (9)
C8—O1—C7—O2	4.6 (4)	C9—C10A—C11—C10B	80.2 (9)
C8—O1—C7—N1	−175.8 (2)	C9—C10B—C11—C12	49.7 (9)
C6—N1—C7—O2	12.6 (4)	C9—C10B—C11—C10A	−70.3 (9)
C6—N1—C7—O1	−166.9 (2)	C10A—C11—C12—C13	8.1 (7)
C7—O1—C8—C15	62.9 (3)	C10B—C11—C12—C13	−13.0 (6)
C7—O1—C8—C16	−60.6 (3)	C10A—C11—C12—C17	−171.4 (5)
C7—O1—C8—C9	−177.0 (2)	C10B—C11—C12—C17	167.5 (5)
O1—C8—C9—C14	−176.2 (3)	C11—C12—C13—C14	5.2 (4)
C15—C8—C9—C14	−59.4 (3)	C17—C12—C13—C14	−175.3 (3)
C16—C8—C9—C14	67.7 (3)	C12—C13—C14—C9	−35.1 (4)
O1—C8—C9—C10B	−65.4 (6)	C10B—C9—C14—C13	68.3 (5)
C15—C8—C9—C10B	51.3 (6)	C10A—C9—C14—C13	52.4 (5)
C16—C8—C9—C10B	178.4 (6)	C8—C9—C14—C13	−173.4 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of C1–C6 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2ⁱ	0.86	2.12	2.969 (3)	170
C13—H13A···Cg1ⁱⁱ	0.97	2.62	3.566 (3)	166

Symmetry codes: (i) x, −y+2, z−1/2; (ii) x+1/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₃NO₂
M_r	273.36
Crystal system, space group	Monoclinic, Cc
Temperature (K)	100
a, b, c (Å)	19.3067 (19), 9.0058 (9), 8.9521 (9)
β (°)	100.964 (3)
V (Å³)	1528.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.58 × 0.20 × 0.10

Data collection
Diffractometer	Bruker APEXII DUO CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.957, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	8744, 2205, 2053
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.154, 1.15
No. of reflections	2205
No. of parameters	187
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.68, −0.76

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of C1–C6 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2ⁱ	0.86	2.12	2.969 (3)	170
C13—H13A···Cg1ⁱⁱ	0.97	2.62	3.566 (3)	166

Symmetry codes: (i) x, −y+2, z−1/2; (ii) x+1/2, y−1/2, z.

Footnotes

‡Thomson Reuters ResearcherID: C-7576-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors would like to acknowledge Universiti Sains Malaysia (USM) for the University Grant (No. 1001/PTEKIND/8140152). HKF and JHG thank USM for the Research University Golden Goose Grant (No. 1001/PFIZIK/811012). JHG also thanks USM for the award of a USM fellowship.

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