tert-Butyl 3-carbamoyl-4-methoxy-imino-3-methyl-piperidine-1-carboxyl-ate.

In the title compound, C(13)H(23)N(3)O(4), the piperidine ring adopts a chair conformation. An intra-molecular N-H⋯O hydrogen bond is observed between the carbamoyl and carboxyl-ate groups. In the crystal structure, mol-ecules form inversion dimers linked by pairs of N-H⋯O hydrogen bonds.

Related literature

For the synthesis and properties of quinolone derivatives, see: Anderson & Osheroff (2001 ▶); Ball et al. (1998 ▶); Choi et al. (2004 ▶); Ray et al. (2005 ▶); Wang, Guo & Wang (2008 ▶); Wang, Liu & Cao (2008 ▶).

Experimental

Crystal data

C13H23N3O4

M = 285.34

Triclinic,

a = 7.3750 (14) Å

b = 10.0132 (16) Å

c = 11.3383 (18) Å

α = 79.5710 (10)°

β = 73.0340 (10)°

γ = 84.973 (2)°

V = 787.1 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 298 (2) K

0.50 × 0.45 × 0.44 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (; Sheldrick, 1996 ▶) T min = 0.946, T max = 0.963

4100 measured reflections

2727 independent reflections

1535 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.176

S = 1.04

2727 reflections

187 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809000634/is2378sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000634/is2378Isup2.hkl

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

C13H23N3O4	Z = 2
Mr = 285.34	F(000) = 308
Triclinic, P1	Dx = 1.204 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3750 (14) Å	Cell parameters from 1147 reflections
b = 10.0132 (16) Å	θ = 2.6–23.6°
c = 11.3383 (18) Å	µ = 0.09 mm−1
α = 79.571 (1)°	T = 298 K
β = 73.034 (1)°	Block, colorless
γ = 84.973 (2)°	0.50 × 0.45 × 0.44 mm
V = 787.1 (2) Å3

Bruker SMART APEX CCD diffractometer	2727 independent reflections
Radiation source: fine-focus sealed tube	1535 reflections with I > 2σ(I)
graphite	Rint = 0.041
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→8
Tmin = 0.946, Tmax = 0.963	k = −11→10
4100 measured reflections	l = −12→13

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)] = 0.056	H-atom parameters constrained
wR(F2) = 0.176	w = 1/[σ2(Fo2) + (0.0793P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
2727 reflections	Δρmax = 0.22 e Å−3
187 parameters	Δρmin = −0.18 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.052 (9)

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.

	x	y	z	Uiso*/Ueq
N1	0.3951 (3)	0.3430 (2)	0.4995 (2)	0.0486 (6)
N2	0.0625 (3)	0.1810 (2)	0.4744 (2)	0.0647 (8)
H2A	0.0302	0.1251	0.4355	0.078*
H2B	0.0918	0.2623	0.4374	0.078*
N3	0.1916 (3)	0.1524 (2)	0.8514 (2)	0.0485 (6)
O1	0.6155 (3)	0.3495 (2)	0.31633 (18)	0.0636 (6)
O2	0.3110 (3)	0.4119 (2)	0.32090 (19)	0.0649 (6)
O3	0.0266 (4)	0.0264 (2)	0.6479 (2)	0.0825 (8)
O4	0.3333 (3)	0.0907 (2)	0.90663 (17)	0.0580 (6)
C1	0.4323 (4)	0.3706 (3)	0.3737 (3)	0.0504 (7)
C2	0.2080 (4)	0.3727 (3)	0.5782 (3)	0.0502 (7)
H2C	0.1290	0.4149	0.5257	0.060*
H2D	0.2180	0.4373	0.6301	0.060*
C3	0.1121 (4)	0.2457 (3)	0.6625 (2)	0.0453 (7)
C4	0.2516 (4)	0.1757 (3)	0.7326 (2)	0.0426 (7)
C5	0.4480 (4)	0.1488 (3)	0.6534 (3)	0.0533 (8)
H5A	0.4454	0.0802	0.6036	0.064*
H5B	0.5289	0.1142	0.7067	0.064*
C6	0.5292 (4)	0.2785 (3)	0.5672 (3)	0.0549 (8)
H6A	0.5545	0.3409	0.6163	0.066*
H6B	0.6480	0.2567	0.5082	0.066*
C7	0.0673 (4)	0.1420 (3)	0.5911 (3)	0.0523 (7)
C8	−0.0772 (4)	0.2898 (3)	0.7492 (3)	0.0632 (9)
H8A	−0.1396	0.2111	0.8017	0.095*
H8B	−0.1565	0.3366	0.6999	0.095*
H8C	−0.0538	0.3494	0.8003	0.095*
C9	0.2502 (5)	0.0608 (4)	1.0379 (3)	0.0750 (10)
H9A	0.2237	0.1438	1.0719	0.112*
H9B	0.3364	0.0036	1.0756	0.112*
H9C	0.1342	0.0148	1.0548	0.112*
C10	0.6835 (5)	0.3554 (3)	0.1795 (3)	0.0698 (10)
C11	0.5789 (7)	0.2537 (4)	0.1411 (4)	0.1179 (17)
H11A	0.5946	0.1648	0.1865	0.177*
H11B	0.6297	0.2525	0.0530	0.177*
H11C	0.4464	0.2796	0.1594	0.177*
C12	0.6609 (5)	0.4976 (3)	0.1139 (3)	0.0817 (11)
H12A	0.5286	0.5235	0.1307	0.123*
H12B	0.7158	0.5015	0.0255	0.123*
H12C	0.7241	0.5588	0.1436	0.123*
C13	0.8911 (6)	0.3152 (5)	0.1616 (4)	0.1190 (17)
H13A	0.9503	0.3801	0.1898	0.179*
H13B	0.9521	0.3132	0.0746	0.179*
H13C	0.9025	0.2267	0.2090	0.179*

	U11	U22	U33	U12	U13	U23
N1	0.0479 (14)	0.0503 (14)	0.0474 (14)	−0.0055 (11)	−0.0176 (11)	0.0010 (11)
N2	0.088 (2)	0.0558 (15)	0.0618 (17)	−0.0246 (13)	−0.0409 (15)	0.0035 (12)
N3	0.0467 (14)	0.0515 (14)	0.0507 (15)	0.0004 (10)	−0.0223 (12)	−0.0041 (11)
O1	0.0670 (15)	0.0675 (14)	0.0497 (13)	−0.0009 (11)	−0.0118 (11)	−0.0012 (10)
O2	0.0748 (15)	0.0634 (13)	0.0592 (13)	−0.0091 (11)	−0.0332 (12)	0.0098 (10)
O3	0.130 (2)	0.0610 (15)	0.0685 (15)	−0.0418 (14)	−0.0493 (15)	0.0113 (11)
O4	0.0497 (12)	0.0750 (14)	0.0472 (12)	0.0076 (10)	−0.0202 (9)	0.0013 (10)
C1	0.060 (2)	0.0407 (16)	0.0516 (18)	−0.0073 (14)	−0.0207 (16)	0.0003 (13)
C2	0.0539 (18)	0.0430 (16)	0.0570 (18)	0.0003 (13)	−0.0233 (15)	−0.0048 (13)
C3	0.0460 (16)	0.0454 (15)	0.0483 (16)	−0.0040 (12)	−0.0214 (13)	−0.0028 (12)
C4	0.0469 (16)	0.0385 (14)	0.0454 (17)	−0.0041 (12)	−0.0180 (13)	−0.0050 (12)
C5	0.0521 (17)	0.0562 (18)	0.0506 (17)	0.0067 (14)	−0.0195 (14)	−0.0023 (14)
C6	0.0487 (17)	0.0651 (19)	0.0513 (18)	−0.0047 (14)	−0.0197 (14)	−0.0001 (14)
C7	0.0566 (18)	0.0502 (18)	0.0550 (19)	−0.0094 (14)	−0.0271 (15)	0.0013 (14)
C8	0.0476 (18)	0.072 (2)	0.066 (2)	0.0032 (15)	−0.0190 (15)	−0.0008 (16)
C9	0.067 (2)	0.106 (3)	0.0469 (19)	0.0100 (19)	−0.0218 (17)	0.0019 (18)
C10	0.091 (3)	0.061 (2)	0.0489 (19)	−0.0032 (18)	−0.0078 (18)	−0.0056 (15)
C11	0.183 (5)	0.084 (3)	0.081 (3)	−0.036 (3)	−0.008 (3)	−0.031 (2)
C12	0.109 (3)	0.071 (2)	0.059 (2)	−0.018 (2)	−0.020 (2)	0.0060 (17)
C13	0.123 (4)	0.124 (4)	0.072 (3)	0.029 (3)	0.012 (3)	0.001 (2)

N1—C1	1.352 (3)	C5—H5B	0.9700
N1—C2	1.447 (3)	C6—H6A	0.9700
N1—C6	1.461 (3)	C6—H6B	0.9700
N2—C7	1.320 (3)	C8—H8A	0.9600
N2—H2A	0.8600	C8—H8B	0.9600
N2—H2B	0.8600	C8—H8C	0.9600
N3—C4	1.274 (3)	C9—H9A	0.9600
N3—O4	1.412 (3)	C9—H9B	0.9600
O1—C1	1.334 (3)	C9—H9C	0.9600
O1—C10	1.477 (4)	C10—C12	1.502 (4)
O2—C1	1.220 (3)	C10—C13	1.512 (5)
O3—C7	1.234 (3)	C10—C11	1.522 (5)
O4—C9	1.421 (3)	C11—H11A	0.9600
C2—C3	1.534 (3)	C11—H11B	0.9600
C2—H2C	0.9700	C11—H11C	0.9600
C2—H2D	0.9700	C12—H12A	0.9600
C3—C4	1.526 (3)	C12—H12B	0.9600
C3—C8	1.536 (4)	C12—H12C	0.9600
C3—C7	1.537 (4)	C13—H13A	0.9600
C4—C5	1.496 (4)	C13—H13B	0.9600
C5—C6	1.528 (4)	C13—H13C	0.9600
C5—H5A	0.9700
C1—N1—C2	120.1 (2)	O3—C7—N2	122.2 (3)
C1—N1—C6	125.2 (2)	O3—C7—C3	118.3 (2)
C2—N1—C6	114.7 (2)	N2—C7—C3	119.4 (2)
C7—N2—H2A	120.0	C3—C8—H8A	109.5
C7—N2—H2B	120.0	C3—C8—H8B	109.5
H2A—N2—H2B	120.0	H8A—C8—H8B	109.5
C4—N3—O4	112.3 (2)	C3—C8—H8C	109.5
C1—O1—C10	121.1 (2)	H8A—C8—H8C	109.5
N3—O4—C9	108.1 (2)	H8B—C8—H8C	109.5
O2—C1—O1	125.0 (3)	O4—C9—H9A	109.5
O2—C1—N1	123.0 (3)	O4—C9—H9B	109.5
O1—C1—N1	112.0 (3)	H9A—C9—H9B	109.5
N1—C2—C3	112.9 (2)	O4—C9—H9C	109.5
N1—C2—H2C	109.0	H9A—C9—H9C	109.5
C3—C2—H2C	109.0	H9B—C9—H9C	109.5
N1—C2—H2D	109.0	O1—C10—C12	110.4 (3)
C3—C2—H2D	109.0	O1—C10—C13	101.3 (3)
H2C—C2—H2D	107.8	C12—C10—C13	110.6 (3)
C4—C3—C2	106.7 (2)	O1—C10—C11	109.4 (3)
C4—C3—C8	113.3 (2)	C12—C10—C11	112.3 (3)
C2—C3—C8	108.6 (2)	C13—C10—C11	112.2 (3)
C4—C3—C7	107.2 (2)	C10—C11—H11A	109.5
C2—C3—C7	114.1 (2)	C10—C11—H11B	109.5
C8—C3—C7	107.1 (2)	H11A—C11—H11B	109.5
N3—C4—C5	127.1 (2)	C10—C11—H11C	109.5
N3—C4—C3	117.0 (2)	H11A—C11—H11C	109.5
C5—C4—C3	115.8 (2)	H11B—C11—H11C	109.5
C4—C5—C6	110.8 (2)	C10—C12—H12A	109.5
C4—C5—H5A	109.5	C10—C12—H12B	109.5
C6—C5—H5A	109.5	H12A—C12—H12B	109.5
C4—C5—H5B	109.5	C10—C12—H12C	109.5
C6—C5—H5B	109.5	H12A—C12—H12C	109.5
H5A—C5—H5B	108.1	H12B—C12—H12C	109.5
N1—C6—C5	110.2 (2)	C10—C13—H13A	109.5
N1—C6—H6A	109.6	C10—C13—H13B	109.5
C5—C6—H6A	109.6	H13A—C13—H13B	109.5
N1—C6—H6B	109.6	C10—C13—H13C	109.5
C5—C6—H6B	109.6	H13A—C13—H13C	109.5
H6A—C6—H6B	108.1	H13B—C13—H13C	109.5
C4—N3—O4—C9	−176.3 (2)	C2—C3—C4—C5	−51.9 (3)
C10—O1—C1—O2	−9.5 (4)	C8—C3—C4—C5	−171.3 (2)
C10—O1—C1—N1	171.7 (2)	C7—C3—C4—C5	70.7 (3)
C2—N1—C1—O2	−5.1 (4)	N3—C4—C5—C6	−124.0 (3)
C6—N1—C1—O2	172.4 (3)	C3—C4—C5—C6	52.5 (3)
C2—N1—C1—O1	173.8 (2)	C1—N1—C6—C5	−122.0 (3)
C6—N1—C1—O1	−8.8 (4)	C2—N1—C6—C5	55.6 (3)
C1—N1—C2—C3	119.1 (3)	C4—C5—C6—N1	−50.8 (3)
C6—N1—C2—C3	−58.6 (3)	C4—C3—C7—O3	47.7 (3)
N1—C2—C3—C4	52.9 (3)	C2—C3—C7—O3	165.5 (3)
N1—C2—C3—C8	175.4 (2)	C8—C3—C7—O3	−74.2 (3)
N1—C2—C3—C7	−65.3 (3)	C4—C3—C7—N2	−136.3 (3)
O4—N3—C4—C5	−2.0 (4)	C2—C3—C7—N2	−18.5 (4)
O4—N3—C4—C3	−178.5 (2)	C8—C3—C7—N2	101.7 (3)
C2—C3—C4—N3	124.9 (2)	C1—O1—C10—C12	66.9 (3)
C8—C3—C4—N3	5.5 (3)	C1—O1—C10—C13	−175.9 (3)
C7—C3—C4—N3	−112.4 (3)	C1—O1—C10—C11	−57.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O2	0.86	2.25	3.026 (3)	150
N2—H2A···O3i	0.86	2.06	2.913 (3)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O2	0.86	2.25	3.026 (3)	150
N2—H2A⋯O3i	0.86	2.06	2.913 (3)	173

Symmetry code: (i) .