tert-Butyl (3-oxo­cyclo­pent­yl)carbamate

In the title compound, C₁₀H₁₇NO₃, the five-membered ring is in a slightly twisted envelope conformation. The carbonyl group is disordered over two sites on the five-membered ring, with refined occupancies of 0.906 (4) and 0.094 (4). In the crystal, mol­ecules are linked via N—H...O hydrogen bonds forming C(4) chains along [001].

Key indicators

• Single-crystal X-ray study
• T = 147 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.050
• wR factor = 0.130
• Data-to-parameter ratio = 18.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         C7 Check
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.827 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          4 Note
PLAT128_ALERT_4_G Alternate Setting for Input Space Group     C2/c       I2/a Note
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          2 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          1 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1)..        21% Note
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          2 Note
PLAT793_ALERT_4_G The Model has Chirality at C1      (Centro SPGR)          S Verify
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         19 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  10 ALERT level G = General information/check it is not something unexpected

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

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Computing details

Data collection: APEX2 (Bruker, 2014); cell refinement: APEX2 (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

tert-Butyl (3-oxocyclopentyl)carbamate

Crystal data

C10H17NO3	F(000) = 864
Mr = 199.24	Dx = 1.181 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 20.6617 (14) Å	Cell parameters from 1745 reflections
b = 11.6924 (9) Å	θ = 2.7–23.5°
c = 9.9566 (7) Å	µ = 0.09 mm^−1
β = 111.295 (4)°	T = 147 K
V = 2241.1 (3) Å^3	Plate, colourless
Z = 8	0.25 × 0.18 × 0.03 mm

Data collection

Bruker Kappa APEX DUO CCD diffractometer	1695 reflections with I > 2σ(I)
Radiation source: sealed tube with Bruker Triumph monochromator	Rint = 0.039
φ and ω scans	θmax = 27.6°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −25→26
Tmin = 0.707, Tmax = 0.746	k = −12→15
8250 measured reflections	l = −12→12
2586 independent reflections

Refinement

Refinement on F^2	1 restraint
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.130	w = 1/[σ^2(Fo^2) + (0.0552P)^2 + 1.179P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
2586 reflections	Δρmax = 0.25 e Å^−3
139 parameters	Δρmin = −0.19 e Å^−3

Special details

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. H atoms were placed in calculated positions with C–H = 0.98–1.00 Å and included in the refinement with U_iso(H)=1.2U_eq(C) or 1.5U_eq(C_methyl). The H atom bonded to N was refined independently with an isotropic displacement parameter.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.52124 (7)	0.36776 (15)	0.60633 (18)	0.0513 (6)	0.906 (4)
C3	0.41982 (10)	0.25014 (18)	0.5483 (2)	0.0392 (5)	0.906 (4)
H3A	0.4309	0.2073	0.6397	0.047*	0.906 (4)
H3B	0.4315	0.2019	0.4785	0.047*	0.906 (4)
C4	0.45871 (10)	0.35970 (18)	0.5731 (2)	0.0401 (5)	0.906 (4)
O1A	0.4615 (8)	0.1760 (13)	0.6013 (19)	0.070 (7)*	0.094 (4)
C3A	0.41982 (10)	0.25014 (18)	0.5483 (2)	0.0392 (5)	0.094 (4)
C4A	0.45871 (10)	0.35970 (18)	0.5731 (2)	0.0401 (5)	0.094 (4)
H4A1	0.4820	0.3682	0.5025	0.048*	0.094 (4)
H4A2	0.4947	0.3607	0.6713	0.048*	0.094 (4)
O2	0.25826 (7)	0.51394 (12)	0.68422 (12)	0.0382 (4)
O3	0.18971 (6)	0.57509 (11)	0.46075 (12)	0.0313 (3)
N1	0.27867 (7)	0.46337 (13)	0.48373 (15)	0.0267 (3)
C1	0.34193 (8)	0.39996 (15)	0.55617 (17)	0.0243 (4)
H1A	0.3463	0.3875	0.6585	0.029*
C2	0.34363 (10)	0.28369 (17)	0.4884 (2)	0.0430 (5)
H2A	0.3150	0.2273	0.5163	0.052*
H2B	0.3263	0.2893	0.3819	0.052*
C5	0.40809 (10)	0.45669 (18)	0.5565 (3)	0.0470 (6)
H5A	0.3996	0.4983	0.4651	0.056*
H5B	0.4261	0.5112	0.6377	0.056*
C6	0.24354 (8)	0.51738 (14)	0.55445 (16)	0.0227 (4)
C7	0.14221 (9)	0.64310 (16)	0.50923 (18)	0.0293 (4)
C8	0.18093 (10)	0.73408 (17)	0.6154 (2)	0.0385 (5)
H8A	0.1477	0.7890	0.6279	0.058*
H8B	0.2129	0.7739	0.5789	0.058*
H8C	0.2073	0.6985	0.7083	0.058*
C9	0.10128 (12)	0.56591 (19)	0.5703 (3)	0.0579 (7)
H9A	0.0678	0.6116	0.5962	0.087*
H9B	0.1330	0.5273	0.6564	0.087*
H9C	0.0765	0.5087	0.4981	0.087*
C10	0.09596 (12)	0.6992 (2)	0.3699 (2)	0.0571 (7)
H10A	0.0612	0.7470	0.3888	0.086*
H10B	0.0724	0.6400	0.2994	0.086*
H10C	0.1243	0.7468	0.3317	0.086*
H1N	0.2658 (10)	0.4773 (17)	0.395 (2)	0.034 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0249 (9)	0.0658 (12)	0.0656 (11)	0.0069 (8)	0.0195 (7)	0.0193 (9)
C3	0.0333 (11)	0.0373 (12)	0.0456 (11)	0.0133 (9)	0.0125 (9)	−0.0024 (9)
C4	0.0285 (10)	0.0502 (13)	0.0451 (11)	0.0095 (9)	0.0174 (8)	0.0094 (10)
C3A	0.0333 (11)	0.0373 (12)	0.0456 (11)	0.0133 (9)	0.0125 (9)	−0.0024 (9)
C4A	0.0285 (10)	0.0502 (13)	0.0451 (11)	0.0095 (9)	0.0174 (8)	0.0094 (10)
O2	0.0476 (8)	0.0512 (9)	0.0206 (6)	0.0204 (7)	0.0183 (5)	0.0060 (6)
O3	0.0293 (7)	0.0413 (8)	0.0226 (6)	0.0156 (6)	0.0086 (5)	−0.0021 (5)
N1	0.0281 (7)	0.0372 (9)	0.0167 (6)	0.0114 (7)	0.0105 (6)	0.0039 (6)
C1	0.0238 (8)	0.0283 (9)	0.0234 (8)	0.0074 (7)	0.0116 (6)	0.0041 (7)
C2	0.0302 (10)	0.0325 (11)	0.0626 (13)	0.0048 (9)	0.0124 (10)	−0.0066 (10)
C5	0.0332 (11)	0.0328 (11)	0.0752 (15)	0.0024 (9)	0.0201 (11)	0.0059 (11)
C6	0.0230 (8)	0.0242 (9)	0.0232 (8)	0.0030 (7)	0.0109 (6)	0.0012 (7)
C7	0.0227 (8)	0.0340 (10)	0.0329 (9)	0.0082 (8)	0.0122 (7)	−0.0047 (8)
C8	0.0363 (10)	0.0341 (11)	0.0453 (11)	0.0060 (9)	0.0150 (9)	−0.0077 (9)
C9	0.0421 (12)	0.0432 (13)	0.104 (2)	−0.0013 (11)	0.0458 (13)	0.0002 (13)
C10	0.0492 (13)	0.0732 (17)	0.0403 (11)	0.0360 (13)	0.0060 (10)	−0.0055 (11)

Geometric parameters (Å, º)

O1—C4	1.215 (2)	C1—C2	1.524 (3)
C3—C4	1.484 (3)	C1—H1A	1.0000
C3—C2	1.518 (3)	C2—H2A	0.9900
C3—H3A	0.9900	C2—H2B	0.9900
C3—H3B	0.9900	C5—H5A	0.9900
C4—C5	1.510 (3)	C5—H5B	0.9900
O1A—C3A	1.201 (9)	C7—C9	1.508 (3)
C3A—C4A	1.484 (3)	C7—C8	1.508 (3)
C3A—C2	1.518 (3)	C7—C10	1.518 (3)
C4A—C5	1.510 (3)	C8—H8A	0.9800
C4A—H4A1	0.9900	C8—H8B	0.9800
C4A—H4A2	0.9900	C8—H8C	0.9800
O2—C6	1.2158 (18)	C9—H9A	0.9800
O3—C6	1.3451 (19)	C9—H9B	0.9800
O3—C7	1.4739 (19)	C9—H9C	0.9800
N1—C6	1.339 (2)	C10—H10A	0.9800
N1—C1	1.447 (2)	C10—H10B	0.9800
N1—H1N	0.84 (2)	C10—H10C	0.9800
C1—C5	1.518 (3)
C4—C3—C2	105.30 (16)	C4A—C5—C1	105.03 (16)
C4—C3—H3A	110.7	C4—C5—C1	105.03 (16)
C2—C3—H3A	110.7	C4—C5—H5A	110.7
C4—C3—H3B	110.7	C1—C5—H5A	110.7
C2—C3—H3B	110.7	C4—C5—H5B	110.7
H3A—C3—H3B	108.8	C1—C5—H5B	110.7
O1—C4—C3	124.75 (19)	H5A—C5—H5B	108.8
O1—C4—C5	126.7 (2)	O2—C6—N1	124.69 (15)
C3—C4—C5	108.55 (16)	O2—C6—O3	125.33 (14)
O1A—C3A—C4A	106.9 (10)	N1—C6—O3	109.98 (13)
O1A—C3A—C2	146.6 (10)	O3—C7—C9	110.30 (15)
C4A—C3A—C2	105.30 (16)	O3—C7—C8	111.30 (14)
C3A—C4A—C5	108.55 (16)	C9—C7—C8	111.84 (17)
C3A—C4A—H4A1	110.0	O3—C7—C10	101.94 (14)
C5—C4A—H4A1	110.0	C9—C7—C10	111.60 (18)
C3A—C4A—H4A2	110.0	C8—C7—C10	109.46 (17)
C5—C4A—H4A2	110.0	C7—C8—H8A	109.5
H4A1—C4A—H4A2	108.4	C7—C8—H8B	109.5
C6—O3—C7	121.65 (12)	H8A—C8—H8B	109.5
C6—N1—C1	122.93 (14)	C7—C8—H8C	109.5
C6—N1—H1N	115.9 (14)	H8A—C8—H8C	109.5
C1—N1—H1N	120.4 (13)	H8B—C8—H8C	109.5
N1—C1—C5	115.27 (15)	C7—C9—H9A	109.5
N1—C1—C2	113.47 (14)	C7—C9—H9B	109.5
C5—C1—C2	103.01 (14)	H9A—C9—H9B	109.5
N1—C1—H1A	108.3	C7—C9—H9C	109.5
C5—C1—H1A	108.3	H9A—C9—H9C	109.5
C2—C1—H1A	108.3	H9B—C9—H9C	109.5
C3A—C2—C1	104.11 (15)	C7—C10—H10A	109.5
C3—C2—C1	104.11 (15)	C7—C10—H10B	109.5
C3—C2—H2A	110.9	H10A—C10—H10B	109.5
C1—C2—H2A	110.9	C7—C10—H10C	109.5
C3—C2—H2B	110.9	H10A—C10—H10C	109.5
C1—C2—H2B	110.9	H10B—C10—H10C	109.5
H2A—C2—H2B	109.0
C2—C3—C4—O1	−171.8 (2)	O1—C4—C5—C1	−164.6 (2)
C2—C3—C4—C5	10.6 (2)	C3—C4—C5—C1	12.9 (2)
O1A—C3A—C4A—C5	−160.6 (10)	N1—C1—C5—C4A	−155.20 (15)
C2—C3A—C4A—C5	10.6 (2)	C2—C1—C5—C4A	−31.1 (2)
C6—N1—C1—C5	−106.9 (2)	N1—C1—C5—C4	−155.20 (15)
C6—N1—C1—C2	134.68 (18)	C2—C1—C5—C4	−31.1 (2)
O1A—C3A—C2—C1	134.5 (17)	C1—N1—C6—O2	−4.3 (3)
C4A—C3A—C2—C1	−30.1 (2)	C1—N1—C6—O3	175.97 (15)
C4—C3—C2—C1	−30.1 (2)	C7—O3—C6—O2	0.7 (3)
N1—C1—C2—C3A	163.07 (15)	C7—O3—C6—N1	−179.64 (15)
C5—C1—C2—C3A	37.8 (2)	C6—O3—C7—C9	−66.5 (2)
N1—C1—C2—C3	163.07 (15)	C6—O3—C7—C8	58.3 (2)
C5—C1—C2—C3	37.8 (2)	C6—O3—C7—C10	174.87 (17)
C3A—C4A—C5—C1	12.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2^i	0.84 (2)	2.05 (2)	2.8684 (17)	164.4 (19)

Symmetry code: (i) x, −y+1, z−1/2.