tert-Butyl 4-(3,4-dichloro-anilino)piperidine-1-carboxyl-ate.

In the title compound, C(16)H(22)Cl(2)N(2)O(2), the substituted piperidine ring adopts a chair conformation with both substituents in equatorial positions. In the crystal, N-H⋯O and C-H⋯O hydrogen bonds connect mol-ecules into ribbons along the a-axis direction.

Related literature

For the biological activity of piperazine derivatives, see: Hamed et al. (2012 ▶); Joergen et al. (1997 ▶); Peter et al. (2009 ▶). For the synthesis of the title compound, see: Vardanyan et al. (2009 ▶).

Experimental

Crystal data

C16H22Cl2N2O2

M = 345.25

Orthorhombic,

a = 9.7825 (6) Å

b = 10.6075 (6) Å

c = 16.8215 (10) Å

V = 1745.53 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.38 mm−1

T = 100 K

0.40 × 0.40 × 0.30 mm

Data collection

Bruker Kappa APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.662, T max = 0.749

34136 measured reflections

13197 independent reflections

11079 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.079

S = 1.00

13197 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶), 6110 Friedel pairs

Flack parameter: −0.01 (2)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812051896/zl2529sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812051896/zl2529Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812051896/zl2529Isup3.cml

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

C16H22Cl2N2O2	Dx = 1.302 Mg m−3
Mr = 345.25	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 9939 reflections
a = 9.7825 (6) Å	θ = 2.8–40.0°
b = 10.6075 (6) Å	µ = 0.38 mm−1
c = 16.8215 (10) Å	T = 100 K
V = 1745.53 (18) Å3	Rod, clear colourless
Z = 4	0.40 × 0.40 × 0.30 mm
F(000) = 728

Bruker Kappa APEXII DUO CCD diffractometer	13197 independent reflections
Radiation source: fine-focus sealed tube	11079 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 8.3333 pixels mm-1	θmax = 43.7°, θmin = 2.3°
φ and ω scans	h = −19→17
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −20→15
Tmin = 0.662, Tmax = 0.749	l = −32→22
34136 measured reflections

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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.079	w = 1/[σ2(Fo2) + (0.0361P)2 + 0.1129P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.002
13197 reflections	Δρmax = 0.44 e Å−3
202 parameters	Δρmin = −0.19 e Å−3
0 restraints	Absolute structure: Flack (1983), ???? Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.01 (2)

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
Cl1	−0.08164 (2)	0.97197 (2)	0.972015 (11)	0.02294 (4)
Cl2	0.13863 (19)	0.75577 (18)	0.941766 (10)	0.01982 (3)
O1	0.10534 (5)	0.83348 (5)	0.29230 (3)	0.01589 (9)
O2	−0.11737 (5)	0.79311 (6)	0.32343 (3)	0.01988 (10)
C14	0.06777 (12)	0.63102 (8)	0.22473 (6)	0.03006 (19)
H14A	0.1276	0.595	0.2655	0.045*
H14B	0.0822	0.5867	0.1743	0.045*
H14C	−0.0278	0.6217	0.2412	0.045*
C3	0.13364 (7)	0.82954 (6)	0.78917 (4)	0.01425 (10)
H3	0.2006	0.7658	0.7815	0.017*
C13	0.10078 (8)	0.77016 (7)	0.21416 (4)	0.01681 (11)
C12	−0.00406 (7)	0.83543 (6)	0.34047 (4)	0.01344 (10)
N2	0.02566 (6)	0.89021 (6)	0.41112 (4)	0.01450 (9)
C10	0.15552 (7)	0.95171 (7)	0.43015 (4)	0.01648 (11)
H10A	0.1433	1.0444	0.4296	0.02*
H10B	0.2247	0.9295	0.3895	0.02*
C11	0.20526 (7)	0.90986 (8)	0.51199 (4)	0.01733 (12)
H11A	0.2881	0.9585	0.5263	0.021*
H11B	0.2306	0.8196	0.5099	0.021*
C7	0.09632 (7)	0.92909 (7)	0.57613 (4)	0.01480 (10)
H7	0.0784	1.0215	0.5816	0.018*
N1	0.14933 (7)	0.88223 (7)	0.65131 (4)	0.01898 (11)
H1	0.2255	0.8381	0.6502	0.023*
C4	0.08893 (7)	0.90197 (6)	0.72395 (4)	0.01433 (10)
C5	−0.01262 (8)	0.99380 (7)	0.73731 (4)	0.01686 (12)
H5	−0.0468	1.0417	0.6939	0.02*
C6	−0.06310 (7)	1.01490 (7)	0.81332 (4)	0.01730 (11)
H6	−0.1303	1.0783	0.8215	0.021*
C1	−0.01660 (7)	0.94440 (7)	0.87772 (4)	0.01538 (11)
C2	0.08092 (7)	0.85036 (6)	0.86435 (4)	0.01397 (10)
C9	−0.08241 (7)	0.91113 (7)	0.46944 (4)	0.01573 (10)
H9A	−0.1662	0.8659	0.4528	0.019*
H9B	−0.1039	1.0022	0.4724	0.019*
C8	−0.03699 (7)	0.86400 (7)	0.55099 (4)	0.01653 (11)
H8A	−0.0228	0.7716	0.549	0.02*
H8B	−0.1092	0.8818	0.5906	0.02*
C16	0.24662 (8)	0.78782 (8)	0.18424 (5)	0.02256 (14)
H16A	0.2688	0.8779	0.1832	0.034*
H16B	0.2547	0.753	0.1305	0.034*
H16C	0.3101	0.7439	0.2198	0.034*
C15	0.00084 (9)	0.83714 (10)	0.15914 (5)	0.02569 (16)
H15A	−0.0908	0.8352	0.1826	0.039*
H15B	−0.0007	0.7944	0.1075	0.039*
H15C	0.0297	0.9249	0.1519	0.039*

	U11	U22	U33	U12	U13	U23
Cl1	0.01965 (7)	0.03505 (10)	0.01412 (7)	0.00661 (7)	0.00311 (6)	0.00055 (6)
Cl2	0.02267 (7)	0.02154 (7)	0.01526 (6)	0.00232 (6)	−0.00074 (6)	0.00598 (6)
O1	0.0154 (2)	0.0189 (2)	0.01340 (19)	−0.00364 (16)	0.00210 (15)	−0.00379 (17)
O2	0.0162 (2)	0.0272 (3)	0.0163 (2)	−0.00867 (19)	−0.00053 (17)	−0.00255 (19)
C14	0.0419 (5)	0.0163 (3)	0.0320 (4)	−0.0073 (3)	0.0078 (4)	−0.0062 (3)
C3	0.0142 (2)	0.0149 (2)	0.0137 (2)	0.0010 (2)	−0.0004 (2)	0.0009 (2)
C13	0.0203 (3)	0.0166 (3)	0.0135 (2)	−0.0034 (2)	0.0022 (2)	−0.0035 (2)
C12	0.0144 (2)	0.0139 (2)	0.0120 (2)	−0.0024 (2)	−0.00017 (19)	0.00076 (19)
N2	0.0122 (2)	0.0189 (2)	0.0124 (2)	−0.00349 (18)	0.00084 (17)	−0.00202 (18)
C10	0.0145 (2)	0.0219 (3)	0.0131 (2)	−0.0061 (2)	−0.0004 (2)	0.0001 (2)
C11	0.0132 (2)	0.0253 (3)	0.0135 (3)	0.0000 (2)	−0.0002 (2)	−0.0005 (2)
C7	0.0151 (2)	0.0174 (3)	0.0119 (2)	0.0014 (2)	−0.00057 (19)	0.0005 (2)
N1	0.0201 (3)	0.0252 (3)	0.0116 (2)	0.0098 (2)	0.0005 (2)	0.0014 (2)
C4	0.0145 (2)	0.0160 (2)	0.0124 (2)	0.0019 (2)	0.0001 (2)	0.00067 (19)
C5	0.0173 (3)	0.0190 (3)	0.0142 (3)	0.0052 (2)	0.0003 (2)	0.0022 (2)
C6	0.0166 (3)	0.0199 (3)	0.0155 (3)	0.0044 (2)	0.0011 (2)	0.0010 (2)
C1	0.0140 (2)	0.0188 (3)	0.0133 (2)	0.0005 (2)	0.0013 (2)	0.0004 (2)
C2	0.0135 (2)	0.0150 (2)	0.0134 (2)	−0.0005 (2)	−0.0013 (2)	0.00250 (19)
C9	0.0132 (2)	0.0197 (3)	0.0143 (2)	−0.0003 (2)	0.0008 (2)	−0.0017 (2)
C8	0.0159 (3)	0.0197 (3)	0.0140 (3)	−0.0014 (2)	0.0024 (2)	0.0007 (2)
C16	0.0219 (3)	0.0250 (3)	0.0208 (3)	−0.0014 (3)	0.0062 (3)	−0.0042 (3)
C15	0.0246 (3)	0.0378 (4)	0.0147 (3)	0.0000 (3)	−0.0006 (3)	0.0007 (3)

Cl1—C1	1.7338 (7)	C7—N1	1.4544 (9)
Cl2—C2	1.7382 (7)	C7—C8	1.5350 (10)
O1—C12	1.3425 (8)	C7—H7	1.0
O1—C13	1.4767 (8)	N1—C4	1.3734 (9)
O2—C12	1.2298 (8)	N1—H1	0.88
C14—C13	1.5213 (11)	C4—C5	1.4093 (10)
C14—H14A	0.98	C5—C6	1.3888 (10)
C14—H14B	0.98	C5—H5	0.95
C14—H14C	0.98	C6—C1	1.3928 (10)
C3—C2	1.3835 (10)	C6—H6	0.95
C3—C4	1.4090 (9)	C1—C2	1.3984 (10)
C3—H3	0.95	C9—C8	1.5261 (10)
C13—C15	1.5223 (12)	C9—H9A	0.99
C13—C16	1.5244 (11)	C9—H9B	0.99
C12—N2	1.3545 (9)	C8—H8A	0.99
N2—C9	1.4592 (9)	C8—H8B	0.99
N2—C10	1.4635 (9)	C16—H16A	0.98
C10—C11	1.5260 (10)	C16—H16B	0.98
C10—H10A	0.99	C16—H16C	0.98
C10—H10B	0.99	C15—H15A	0.98
C11—C7	1.5302 (10)	C15—H15B	0.98
C11—H11A	0.99	C15—H15C	0.98
C11—H11B	0.99
C12—O1—C13	121.34 (5)	C4—N1—H1	117.7
C13—C14—H14A	109.5	C7—N1—H1	117.7
C13—C14—H14B	109.5	N1—C4—C3	118.43 (6)
H14A—C14—H14B	109.5	N1—C4—C5	123.40 (6)
C13—C14—H14C	109.5	C3—C4—C5	118.14 (6)
H14A—C14—H14C	109.5	C6—C5—C4	120.58 (6)
H14B—C14—H14C	109.5	C6—C5—H5	119.7
C2—C3—C4	120.59 (6)	C4—C5—H5	119.7
C2—C3—H3	119.7	C5—C6—C1	120.90 (7)
C4—C3—H3	119.7	C5—C6—H6	119.6
O1—C13—C15	110.38 (6)	C1—C6—H6	119.6
O1—C13—C16	102.11 (6)	C6—C1—C2	118.73 (6)
C15—C13—C16	110.06 (7)	C6—C1—Cl1	120.08 (5)
O1—C13—C14	110.10 (6)	C2—C1—Cl1	121.19 (5)
C15—C13—C14	112.80 (7)	C3—C2—C1	121.01 (6)
C16—C13—C14	110.89 (7)	C3—C2—Cl2	118.14 (5)
O2—C12—O1	124.91 (6)	C1—C2—Cl2	120.85 (5)
O2—C12—N2	123.67 (6)	N2—C9—C8	110.10 (6)
O1—C12—N2	111.42 (6)	N2—C9—H9A	109.6
C12—N2—C9	119.98 (6)	C8—C9—H9A	109.6
C12—N2—C10	124.71 (6)	N2—C9—H9B	109.6
C9—N2—C10	114.45 (6)	C8—C9—H9B	109.6
N2—C10—C11	110.14 (6)	H9A—C9—H9B	108.2
N2—C10—H10A	109.6	C9—C8—C7	110.34 (6)
C11—C10—H10A	109.6	C9—C8—H8A	109.6
N2—C10—H10B	109.6	C7—C8—H8A	109.6
C11—C10—H10B	109.6	C9—C8—H8B	109.6
H10A—C10—H10B	108.1	C7—C8—H8B	109.6
C10—C11—C7	112.04 (6)	H8A—C8—H8B	108.1
C10—C11—H11A	109.2	C13—C16—H16A	109.5
C7—C11—H11A	109.2	C13—C16—H16B	109.5
C10—C11—H11B	109.2	H16A—C16—H16B	109.5
C7—C11—H11B	109.2	C13—C16—H16C	109.5
H11A—C11—H11B	107.9	H16A—C16—H16C	109.5
N1—C7—C11	108.61 (6)	H16B—C16—H16C	109.5
N1—C7—C8	112.88 (6)	C13—C15—H15A	109.5
C11—C7—C8	109.72 (6)	C13—C15—H15B	109.5
N1—C7—H7	108.5	H15A—C15—H15B	109.5
C11—C7—H7	108.5	C13—C15—H15C	109.5
C8—C7—H7	108.5	H15A—C15—H15C	109.5
C4—N1—C7	124.62 (6)	H15B—C15—H15C	109.5
C12—O1—C13—C15	65.40 (8)	C2—C3—C4—N1	176.69 (7)
C12—O1—C13—C16	−177.61 (6)	C2—C3—C4—C5	−1.34 (10)
C12—O1—C13—C14	−59.79 (9)	N1—C4—C5—C6	−175.62 (7)
C13—O1—C12—O2	−4.42 (11)	C3—C4—C5—C6	2.31 (11)
C13—O1—C12—N2	175.50 (6)	C4—C5—C6—C1	−1.23 (12)
O2—C12—N2—C9	−5.18 (11)	C5—C6—C1—C2	−0.86 (11)
O1—C12—N2—C9	174.90 (6)	C5—C6—C1—Cl1	−179.73 (6)
O2—C12—N2—C10	−174.00 (7)	C4—C3—C2—C1	−0.72 (11)
O1—C12—N2—C10	6.08 (10)	C4—C3—C2—Cl2	178.95 (5)
C12—N2—C10—C11	−134.30 (7)	C6—C1—C2—C3	1.83 (11)
C9—N2—C10—C11	56.33 (8)	Cl1—C1—C2—C3	−179.31 (6)
N2—C10—C11—C7	−53.30 (8)	C6—C1—C2—Cl2	−177.83 (6)
C10—C11—C7—N1	177.63 (6)	Cl1—C1—C2—Cl2	1.03 (9)
C10—C11—C7—C8	53.82 (8)	C12—N2—C9—C8	131.49 (7)
C11—C7—N1—C4	169.17 (7)	C10—N2—C9—C8	−58.59 (8)
C8—C7—N1—C4	−68.92 (9)	N2—C9—C8—C7	56.87 (7)
C7—N1—C4—C3	166.47 (7)	N1—C7—C8—C9	−176.41 (6)
C7—N1—C4—C5	−15.61 (12)	C11—C7—C8—C9	−55.13 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.88	2.12	2.9740 (8)	163
C3—H3···O2i	0.95	2.58	3.3486 (9)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.88	2.12	2.9740 (8)	163
C3—H3⋯O2i	0.95	2.58	3.3486 (9)	138

Symmetry code: (i) .