2-(4-Methyl-cyclo-hex-3-en-yl)propan-2-yl N-phenyl-carbamate.

In the title carbamate compound, C(17)H(23)NO(2), one of the Csp(3) atoms of the cyclo-hexene 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 inter-planar 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 cyclo-hexene rings. In the crystal structure, adjacent mol-ecules are linked into chains along [001] via inter-molecular N-H⋯O hydrogen bonds. The crystal structure is further stabilized by weak inter-molecular C-H⋯π inter-actions.

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 = 273.36

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.154

S = 1.15

2205 reflections

187 parameters

4 restraints

H-atom parameters constrained

Δρmax = 0.68 e Å−3

Δρmin = −0.76 e Å−3

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 ▶).

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025080/hb5524Isup2.hkl

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

C17H23NO2	F(000) = 592
Mr = 273.36	Dx = 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

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

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(Fo2) + (0.0981P)2 + 0.223P] where P = (Fo2 + 2Fc2)/3
S = 1.15	(Δ/σ)max < 0.001
2205 reflections	Δρmax = 0.68 e Å−3
187 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq	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*

	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)

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)

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

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) ; (ii) .