5-(tert-Butylamino)-5-oxopentanoic acid

The title novel carboxylic acid derivative, C₉H₁₇NO₃, containing the tert-butyl­carbamoyl group, has been synthesized by the reaction of glutaric anhydride and tert-butyl­amine. In the crystal structure, this compound forms intermolecular hydrogen bonds between the amide and carboxyl groups. However, it does not form a hydrogen-bonded dimer involving two carboxylic acid groups.

Key indicators

• Single-crystal X-ray study
• T = 200 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.034
• wR factor = 0.088
• Data-to-parameter ratio = 10.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.99
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         C6

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               1246
           Count of symmetry unique reflns         1263
           Completeness (_total/calc)             98.65%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

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

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

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Computing details

Data collection: PROCESS-AUTO (Rigaku Corporation, 1998); cell refinement: PROCESS-AUTO; data reduction: TEXSAN (Molecular Structure Corporation, 2000); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: TEXSAN and Mercury (Bruno et al., 2002); software used to prepare material for publication: TEXSAN and Mercury.

5-(tert-Butylamino)-5-oxopentanoic acid

Crystal data

C9H17NO3	F(000) = 204
Mr = 187.24	Dx = 1.187 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2yb	Cell parameters from 5001 reflections
a = 6.066 (3) Å	θ = 2.6–27.5°
b = 11.076 (6) Å	µ = 0.09 mm^−1
c = 7.797 (3) Å	T = 200 K
β = 91.56 (4)°	Block, colourless
V = 523.7 (4) Å^3	0.50 × 0.50 × 0.20 mm
Z = 2

Data collection

Rigaku RAXIS-RAPID imaging-plate diffractometer	1128 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
Graphite monochromator	θmax = 27.5°, θmin = 2.6°
Detector resolution: 10.00 pixels mm^-1	h = −7→7
ω scans	k = −14→14
5164 measured reflections	l = −10→8
1246 independent reflections

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.088	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0647P)^2] where P = (Fo^2 + 2Fc^2)/3
1246 reflections	(Δ/σ)max < 0.001
119 parameters	Δρmax = 0.14 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
O1	0.1747 (2)	0.26696 (13)	0.22341 (18)	0.0406 (3)
O2	0.6773 (2)	0.03690 (14)	0.58867 (19)	0.0413 (3)
O3	0.4779 (2)	−0.10768 (12)	0.7046 (2)	0.0425 (4)
H2	0.6030	−0.1364	0.7294	0.051*
N1	−0.1188 (2)	0.15204 (13)	0.28805 (18)	0.0290 (3)
H1	−0.2022	0.1282	0.3722	0.035*
C1	0.5006 (3)	−0.00441 (15)	0.6245 (2)	0.0299 (4)
C2	0.2831 (3)	0.05516 (16)	0.5802 (3)	0.0339 (4)
H3	0.1707	0.0253	0.6596	0.041*
H4	0.2361	0.0314	0.4624	0.041*
C3	0.2926 (3)	0.19240 (15)	0.5907 (3)	0.0342 (4)
H5	0.4195	0.2216	0.5253	0.041*
H6	0.3168	0.2167	0.7120	0.041*
C4	0.0811 (3)	0.25237 (16)	0.5199 (2)	0.0324 (4)
H7	−0.0468	0.2225	0.5837	0.039*
H8	0.0911	0.3408	0.5367	0.039*
C5	0.0466 (3)	0.22501 (15)	0.3306 (2)	0.0292 (4)
C6	−0.1795 (3)	0.10586 (17)	0.1145 (2)	0.0321 (4)
C7	−0.2371 (5)	0.2093 (2)	−0.0059 (3)	0.0602 (7)
H9	−0.3585	0.2563	0.0409	0.072*
H10	−0.2821	0.1771	−0.1186	0.072*
H11	−0.1079	0.2615	−0.0180	0.072*
C8	0.0072 (4)	0.0316 (3)	0.0460 (3)	0.0556 (6)
H12	0.1364	0.0833	0.0312	0.067*
H13	−0.0380	−0.0035	−0.0649	0.067*
H14	0.0444	−0.0333	0.1272	0.067*
C9	−0.3794 (4)	0.0256 (3)	0.1382 (3)	0.0633 (7)
H15	−0.5005	0.0738	0.1829	0.076*
H16	−0.3415	−0.0391	0.2195	0.076*
H17	−0.4250	−0.0096	0.0275	0.076*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0476 (8)	0.0375 (7)	0.0370 (7)	−0.0165 (6)	0.0043 (5)	−0.0043 (6)
O2	0.0344 (7)	0.0402 (7)	0.0491 (8)	−0.0006 (6)	0.0006 (5)	0.0108 (6)
O3	0.0407 (7)	0.0304 (7)	0.0567 (9)	0.0055 (6)	0.0071 (6)	0.0138 (6)
N1	0.0295 (7)	0.0289 (7)	0.0285 (7)	−0.0007 (5)	−0.0009 (5)	0.0004 (5)
C1	0.0349 (9)	0.0273 (8)	0.0274 (9)	0.0004 (6)	−0.0004 (6)	0.0015 (6)
C2	0.0322 (9)	0.0285 (9)	0.0409 (10)	−0.0012 (7)	−0.0022 (7)	0.0038 (7)
C3	0.0384 (9)	0.0266 (8)	0.0373 (10)	−0.0011 (7)	−0.0079 (7)	−0.0020 (7)
C4	0.0381 (9)	0.0262 (8)	0.0326 (9)	0.0022 (7)	−0.0033 (6)	−0.0039 (7)
C5	0.0320 (8)	0.0218 (7)	0.0336 (9)	0.0031 (6)	−0.0014 (6)	−0.0019 (6)
C6	0.0317 (9)	0.0328 (9)	0.0316 (9)	−0.0016 (7)	−0.0025 (6)	−0.0055 (7)
C7	0.100 (2)	0.0452 (12)	0.0343 (12)	0.0103 (13)	−0.0198 (12)	−0.0030 (9)
C8	0.0464 (11)	0.0584 (14)	0.0616 (15)	0.0100 (11)	−0.0049 (10)	−0.0297 (12)
C9	0.0531 (13)	0.088 (2)	0.0482 (13)	−0.0350 (14)	−0.0031 (10)	−0.0129 (13)

Geometric parameters (Å, º)

O1—C5	1.247 (2)	C4—H7	0.9900
O2—C1	1.205 (2)	C4—H8	0.9900
O3—C1	1.312 (2)	C6—C8	1.509 (3)
O3—H2	0.8400	C6—C7	1.516 (3)
N1—C5	1.323 (2)	C6—C9	1.519 (3)
N1—C6	1.484 (2)	C7—H9	0.9800
N1—H1	0.8800	C7—H10	0.9800
C1—C2	1.507 (3)	C7—H11	0.9800
C2—C3	1.523 (2)	C8—H12	0.9800
C2—H3	0.9900	C8—H13	0.9800
C2—H4	0.9900	C8—H14	0.9800
C3—C4	1.534 (3)	C9—H15	0.9800
C3—H5	0.9900	C9—H16	0.9800
C3—H6	0.9900	C9—H17	0.9800
C4—C5	1.515 (3)
C1—O3—H2	109.5	O1—C5—C4	120.41 (16)
C5—N1—C6	127.37 (15)	N1—C5—C4	116.76 (16)
C5—N1—H1	116.3	N1—C6—C8	109.92 (16)
C6—N1—H1	116.3	N1—C6—C7	110.59 (16)
O2—C1—O3	123.13 (16)	C8—C6—C7	110.8 (2)
O2—C1—C2	124.01 (16)	N1—C6—C9	105.66 (16)
O3—C1—C2	112.85 (15)	C8—C6—C9	109.5 (2)
C1—C2—C3	113.15 (15)	C7—C6—C9	110.3 (2)
C1—C2—H3	108.9	C6—C7—H9	109.5
C3—C2—H3	108.9	C6—C7—H10	109.5
C1—C2—H4	108.9	H9—C7—H10	109.5
C3—C2—H4	108.9	C6—C7—H11	109.5
H3—C2—H4	107.8	H9—C7—H11	109.5
C2—C3—C4	112.51 (15)	H10—C7—H11	109.5
C2—C3—H5	109.1	C6—C8—H12	109.5
C4—C3—H5	109.1	C6—C8—H13	109.5
C2—C3—H6	109.1	H12—C8—H13	109.5
C4—C3—H6	109.1	C6—C8—H14	109.5
H5—C3—H6	107.8	H12—C8—H14	109.5
C5—C4—C3	110.88 (15)	H13—C8—H14	109.5
C5—C4—H7	109.5	C6—C9—H15	109.5
C3—C4—H7	109.5	C6—C9—H16	109.5
C5—C4—H8	109.5	H15—C9—H16	109.5
C3—C4—H8	109.5	C6—C9—H17	109.5
H7—C4—H8	108.1	H15—C9—H17	109.5
O1—C5—N1	122.78 (17)	H16—C9—H17	109.5
O2—C1—C2—C3	−35.7 (3)	C3—C4—C5—O1	−67.5 (2)
O3—C1—C2—C3	145.20 (18)	C3—C4—C5—N1	110.05 (18)
C1—C2—C3—C4	171.43 (15)	C5—N1—C6—C8	61.5 (3)
C2—C3—C4—C5	−63.0 (2)	C5—N1—C6—C7	−61.1 (2)
C6—N1—C5—O1	1.3 (3)	C5—N1—C6—C9	179.6 (2)
C6—N1—C5—C4	−176.27 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H2···O1^i	0.84	1.75	2.573 (2)	165
N1—H1···O2^ii	0.88	2.11	2.968 (2)	163

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