Methyl N-cyclo­hexyl­carbamate

The structure of the title compound, C₈H₁₅NO₂, is normal and contains a six-membered ring with a chair conformation. The crystal structure is stabilized by inter­molecular N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.038
• wR factor = 0.105
• Data-to-parameter ratio = 10.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.48
           From the CIF: _reflns_number_total               1079
           Count of symmetry unique reflns         1078
           Completeness (_total/calc)            100.09%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         1
           Fraction of Friedel pairs measured     0.001
           Are heavy atom types Z>Si present         no
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Methyl N-cyclohexylcarbamate

Crystal data

C8H15NO2	Dx = 1.176 Mg m^−3
Mr = 157.21	Melting point: 349.65 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 6439 reflections
a = 10.031 (2) Å	θ = 3.1–27.5°
b = 8.7863 (18) Å	µ = 0.08 mm^−1
c = 10.070 (2) Å	T = 293 K
V = 887.6 (3) Å^3	Block, colorless
Z = 4	0.26 × 0.25 × 0.18 mm
F(000) = 344

Data collection

Rigkau R-AXIS RAPID IP area-detector diffractometer	1079 independent reflections
Radiation source: rotating anode	885 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −13→12
Tmin = 0.979, Tmax = 0.985	k = −11→11
8264 measured reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.105	H-atom parameters constrained
S = 1.16	w = 1/[σ^2(Fo^2) + (0.0639P)^2] where P = (Fo^2 + 2Fc^2)/3
1079 reflections	(Δ/σ)max < 0.001
100 parameters	Δρmax = 0.10 e Å^−3
1 restraint	Δρmin = −0.17 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.67522 (15)	0.2360 (2)	0.70059 (19)	0.0566 (5)
H1A	0.7519	0.2557	0.6664	0.068*
O1	0.46094 (12)	0.1748 (2)	0.6534 (2)	0.0667 (4)
O2	0.61010 (16)	0.22375 (18)	0.49088 (17)	0.0659 (4)
C1	0.7721 (2)	0.1373 (3)	0.9074 (2)	0.0589 (5)
H1B	0.7640	0.0333	0.8761	0.071*
H1C	0.8585	0.1755	0.8799	0.071*
C2	0.7638 (2)	0.1390 (3)	1.0574 (3)	0.0697 (6)
H2A	0.8381	0.0819	1.0938	0.084*
H2B	0.6820	0.0895	1.0852	0.084*
C3	0.7668 (3)	0.2997 (3)	1.1118 (3)	0.0765 (7)
H3A	0.7551	0.2971	1.2074	0.092*
H3B	0.8528	0.3456	1.0931	0.092*
C4	0.6579 (3)	0.3943 (3)	1.0499 (3)	0.0743 (7)
H4A	0.5719	0.3545	1.0771	0.089*
H4B	0.6647	0.4981	1.0821	0.089*
C5	0.6659 (2)	0.3945 (3)	0.9004 (3)	0.0628 (6)
H5A	0.7475	0.4446	0.8729	0.075*
H5B	0.5914	0.4517	0.8646	0.075*
C6	0.66334 (18)	0.2338 (2)	0.8446 (2)	0.0488 (5)
H6A	0.5771	0.1882	0.8671	0.059*
C7	0.57362 (17)	0.2090 (2)	0.6192 (2)	0.0485 (4)
C8	0.5082 (3)	0.1943 (4)	0.3950 (3)	0.0745 (7)
H8A	0.5436	0.2086	0.3073	0.112*
H8B	0.4352	0.2631	0.4089	0.112*
H8C	0.4775	0.0914	0.4045	0.112*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0387 (8)	0.0845 (12)	0.0466 (10)	−0.0105 (7)	0.0019 (7)	−0.0024 (9)
O1	0.0417 (7)	0.1019 (11)	0.0564 (9)	−0.0094 (7)	0.0022 (7)	−0.0086 (9)
O2	0.0574 (8)	0.0942 (10)	0.0459 (9)	−0.0081 (7)	−0.0010 (7)	−0.0015 (8)
C1	0.0504 (10)	0.0626 (11)	0.0636 (13)	0.0031 (9)	−0.0004 (10)	0.0043 (10)
C2	0.0622 (13)	0.0843 (16)	0.0626 (13)	−0.0117 (12)	−0.0073 (12)	0.0169 (12)
C3	0.0670 (13)	0.1077 (18)	0.0548 (13)	−0.0207 (12)	−0.0126 (12)	−0.0041 (14)
C4	0.0743 (15)	0.0792 (17)	0.0694 (15)	−0.0045 (12)	−0.0033 (13)	−0.0249 (13)
C5	0.0638 (12)	0.0587 (12)	0.0661 (13)	−0.0015 (9)	−0.0055 (11)	−0.0051 (11)
C6	0.0403 (8)	0.0606 (11)	0.0455 (10)	−0.0054 (8)	0.0006 (8)	−0.0027 (9)
C7	0.0422 (9)	0.0552 (9)	0.0480 (11)	0.0014 (7)	0.0029 (8)	−0.0030 (8)
C8	0.0722 (14)	0.1008 (18)	0.0506 (13)	−0.0019 (13)	−0.0127 (12)	−0.0004 (13)

Geometric parameters (Å, º)

N1—C7	1.329 (3)	C3—C4	1.508 (4)
N1—C6	1.455 (3)	C3—H3A	0.9700
N1—H1A	0.8600	C3—H3B	0.9700
O1—C7	1.219 (2)	C4—C5	1.508 (4)
O2—C7	1.349 (3)	C4—H4A	0.9700
O2—C8	1.429 (3)	C4—H4B	0.9700
C1—C2	1.513 (4)	C5—C6	1.520 (3)
C1—C6	1.520 (3)	C5—H5A	0.9700
C1—H1B	0.9700	C5—H5B	0.9700
C1—H1C	0.9700	C6—H6A	0.9800
C2—C3	1.515 (4)	C8—H8A	0.9600
C2—H2A	0.9700	C8—H8B	0.9600
C2—H2B	0.9700	C8—H8C	0.9600
C7—N1—C6	123.34 (17)	C5—C4—H4B	109.2
C7—N1—H1A	118.3	C3—C4—H4B	109.2
C6—N1—H1A	118.3	H4A—C4—H4B	107.9
C7—O2—C8	115.81 (19)	C4—C5—C6	111.6 (2)
C2—C1—C6	111.8 (2)	C4—C5—H5A	109.3
C2—C1—H1B	109.3	C6—C5—H5A	109.3
C6—C1—H1B	109.3	C4—C5—H5B	109.3
C2—C1—H1C	109.3	C6—C5—H5B	109.3
C6—C1—H1C	109.3	H5A—C5—H5B	108.0
H1B—C1—H1C	107.9	N1—C6—C1	111.31 (18)
C1—C2—C3	111.7 (2)	N1—C6—C5	110.81 (18)
C1—C2—H2A	109.3	C1—C6—C5	110.61 (18)
C3—C2—H2A	109.3	N1—C6—H6A	108.0
C1—C2—H2B	109.3	C1—C6—H6A	108.0
C3—C2—H2B	109.3	C5—C6—H6A	108.0
H2A—C2—H2B	107.9	O1—C7—N1	125.5 (2)
C4—C3—C2	110.5 (2)	O1—C7—O2	123.10 (19)
C4—C3—H3A	109.6	N1—C7—O2	111.45 (15)
C2—C3—H3A	109.6	O2—C8—H8A	109.5
C4—C3—H3B	109.6	O2—C8—H8B	109.5
C2—C3—H3B	109.6	H8A—C8—H8B	109.5
H3A—C3—H3B	108.1	O2—C8—H8C	109.5
C5—C4—C3	112.0 (2)	H8A—C8—H8C	109.5
C5—C4—H4A	109.2	H8B—C8—H8C	109.5
C3—C4—H4A	109.2
C6—C1—C2—C3	−55.2 (3)	C2—C1—C6—C5	54.2 (2)
C1—C2—C3—C4	55.2 (3)	C4—C5—C6—N1	−178.28 (19)
C2—C3—C4—C5	−55.6 (3)	C4—C5—C6—C1	−54.3 (3)
C3—C4—C5—C6	55.8 (3)	C6—N1—C7—O1	−2.5 (3)
C7—N1—C6—C1	130.7 (2)	C6—N1—C7—O2	177.63 (18)
C7—N1—C6—C5	−105.7 (2)	C8—O2—C7—O1	−0.9 (3)
C2—C1—C6—N1	177.84 (19)	C8—O2—C7—N1	178.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1^i	0.86	2.19	3.009 (2)	160

Symmetry code: (i) x+1/2, −y+1/2, z.