Methyl 4-(4-chloro­phen­yl)-1-methyl­piperidine-4-carboxyl­ate

The title compound, C₁₄H₁₈ClNO₂, was synthesized by the reaction of arecoline with 4-chloro­phenyl­magnesium bromide. In the crystal structure, a single weak inter­molecular C—H...O hydrogen bond links mol­ecules into one-dimensional chains along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.040
• wR factor = 0.112
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT391_ALERT_3_C Deviating Methyl C11     H-C-H Bond Angle ......     118.00 Deg.

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

   0 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2003); software used to prepare material for publication: SHELXTL.

methyl 4-(4-chlorophenyl)-1-methylpiperidine-4-carboxylate

Crystal data

C14H18ClNO2	Z = 2
Mr = 267.74	F(000) = 284
Triclinic, P1	Dx = 1.264 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.4546 (11) Å	Cell parameters from 2050 reflections
b = 10.238 (2) Å	θ = 3.1–27.5°
c = 13.615 (3) Å	µ = 0.27 mm^−1
α = 69.01 (3)°	T = 298 K
β = 84.09 (3)°	Prism, colorless
γ = 83.24 (3)°	0.25 × 0.22 × 0.18 mm
V = 703.4 (3) Å^3

Data collection

Bruker SMART CCD APEX-II diffractometer	3187 independent reflections
Radiation source: fine-focus sealed tube	2350 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
Detector resolution: 8.20 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −7→6
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→13
Tmin = 0.93, Tmax = 0.95	l = −17→17
6981 measured 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	All H-atom parameters refined
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0567P)^2 + 0.0857P] where P = (Fo^2 + 2Fc^2)/3
3187 reflections	(Δ/σ)max = 0.002
235 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.19 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
Cl	0.43404 (12)	0.67712 (6)	0.27134 (4)	0.0794 (2)
O1	0.06892 (19)	0.62876 (12)	0.73732 (9)	0.0558 (3)
O2	0.25666 (19)	0.48660 (10)	0.87963 (8)	0.0469 (3)
N1	0.3172 (3)	0.82552 (14)	0.87380 (10)	0.0506 (3)
C1	0.2488 (3)	0.79405 (19)	0.41425 (13)	0.0542 (4)
H18	0.112 (4)	0.827 (2)	0.3727 (16)	0.066 (5)*
C2	0.6381 (3)	0.65966 (18)	0.44864 (14)	0.0535 (4)
H17	0.772 (4)	0.605 (2)	0.4300 (17)	0.078 (6)*
C3	0.3212 (5)	0.95217 (18)	0.77948 (15)	0.0606 (5)
H16	0.481 (4)	0.996 (2)	0.7699 (16)	0.073 (6)*
H15	0.201 (4)	1.020 (2)	0.7900 (16)	0.070 (6)*
C4	0.2779 (4)	0.92191 (16)	0.68180 (13)	0.0500 (4)
H14	0.112 (3)	0.8902 (17)	0.6893 (13)	0.049 (4)*
H13	0.289 (3)	1.008 (2)	0.6198 (15)	0.059 (5)*
C5	0.4705 (2)	0.67748 (14)	0.76952 (10)	0.0361 (3)
H12	0.609 (3)	0.6114 (16)	0.7637 (12)	0.038 (4)*
C6	0.6423 (3)	0.69100 (17)	0.53889 (12)	0.0472 (4)
H11	0.776 (3)	0.6566 (18)	0.5811 (14)	0.056 (5)*
C7	0.2549 (3)	0.82377 (18)	0.50507 (12)	0.0496 (4)
H10	0.125 (4)	0.881 (2)	0.5223 (15)	0.060 (5)*
C8	0.2422 (2)	0.59953 (14)	0.79079 (10)	0.0361 (3)
C9	0.5120 (3)	0.72103 (17)	0.86209 (12)	0.0451 (3)
H9	0.513 (3)	0.6380 (18)	0.9289 (14)	0.047 (4)*
H8	0.678 (3)	0.7572 (18)	0.8494 (14)	0.056 (5)*
C10	0.4412 (3)	0.71253 (16)	0.38681 (12)	0.0488 (4)
C11	0.0520 (4)	0.4003 (2)	0.90636 (17)	0.0599 (5)
H7	0.044 (4)	0.371 (2)	0.851 (2)	0.082 (7)*
H6	0.078 (4)	0.332 (3)	0.972 (2)	0.091 (7)*
H5	−0.112 (5)	0.458 (3)	0.913 (2)	0.107 (8)*
C12	0.4511 (2)	0.77338 (14)	0.56916 (11)	0.0387 (3)
C13	0.4679 (3)	0.80729 (15)	0.66755 (11)	0.0392 (3)
H4	0.628 (3)	0.8388 (16)	0.6619 (12)	0.042 (4)*
C14	0.3544 (6)	0.8595 (3)	0.96614 (17)	0.0740 (6)
H3	0.235 (5)	0.927 (3)	0.974 (2)	0.093 (8)*
H2	0.351 (4)	0.773 (3)	1.030 (2)	0.086 (7)*
H1	0.506 (5)	0.902 (3)	0.9574 (19)	0.086 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.1200 (5)	0.0762 (3)	0.0539 (3)	−0.0072 (3)	−0.0113 (3)	−0.0362 (2)
O1	0.0389 (5)	0.0663 (7)	0.0513 (6)	−0.0139 (5)	−0.0125 (5)	−0.0018 (5)
O2	0.0509 (6)	0.0456 (6)	0.0393 (5)	−0.0138 (5)	−0.0071 (4)	−0.0048 (4)
N1	0.0651 (8)	0.0518 (7)	0.0404 (7)	−0.0121 (6)	0.0023 (6)	−0.0221 (6)
C1	0.0537 (9)	0.0648 (10)	0.0420 (8)	−0.0036 (8)	−0.0105 (7)	−0.0148 (7)
C2	0.0578 (10)	0.0527 (9)	0.0502 (9)	0.0023 (8)	0.0000 (8)	−0.0212 (7)
C3	0.0848 (13)	0.0448 (9)	0.0556 (10)	−0.0068 (9)	0.0011 (9)	−0.0230 (8)
C4	0.0641 (10)	0.0386 (8)	0.0427 (8)	−0.0013 (7)	−0.0009 (7)	−0.0104 (6)
C5	0.0324 (6)	0.0400 (7)	0.0355 (7)	−0.0034 (6)	−0.0050 (5)	−0.0121 (6)
C6	0.0439 (8)	0.0520 (8)	0.0432 (8)	0.0007 (7)	−0.0047 (7)	−0.0144 (7)
C7	0.0445 (8)	0.0606 (9)	0.0411 (8)	0.0040 (7)	−0.0028 (7)	−0.0173 (7)
C8	0.0358 (6)	0.0386 (7)	0.0328 (6)	−0.0027 (6)	−0.0014 (5)	−0.0115 (5)
C9	0.0477 (8)	0.0512 (8)	0.0386 (7)	−0.0139 (7)	−0.0060 (6)	−0.0145 (7)
C10	0.0657 (10)	0.0451 (8)	0.0369 (7)	−0.0117 (7)	−0.0019 (7)	−0.0140 (6)
C11	0.0648 (11)	0.0584 (10)	0.0511 (10)	−0.0279 (9)	−0.0009 (9)	−0.0066 (9)
C12	0.0375 (7)	0.0412 (7)	0.0336 (7)	−0.0095 (6)	0.0024 (5)	−0.0078 (5)
C13	0.0377 (7)	0.0423 (7)	0.0362 (7)	−0.0094 (6)	−0.0004 (6)	−0.0106 (6)
C14	0.1032 (18)	0.0792 (14)	0.0556 (12)	−0.0241 (14)	0.0020 (11)	−0.0399 (11)

Geometric parameters (Å, º)

Cl—C10	1.7404 (16)	C5—C8	1.5048 (19)
O1—C8	1.1968 (17)	C5—C9	1.524 (2)
O2—C8	1.3424 (17)	C5—C13	1.540 (2)
O2—C11	1.441 (2)	C5—H12	0.971 (15)
N1—C9	1.455 (2)	C6—C12	1.386 (2)
N1—C14	1.458 (2)	C6—H11	0.933 (19)
N1—C3	1.462 (2)	C7—C12	1.383 (2)
C1—C10	1.369 (2)	C7—H10	0.932 (19)
C1—C7	1.380 (2)	C9—H9	0.998 (17)
C1—H18	0.94 (2)	C9—H8	0.995 (19)
C2—C10	1.371 (2)	C11—H7	0.92 (2)
C2—C6	1.380 (2)	C11—H6	0.93 (3)
C2—H17	0.94 (2)	C11—H5	1.03 (3)
C3—C4	1.516 (2)	C12—C13	1.513 (2)
C3—H16	1.00 (2)	C13—H4	0.954 (16)
C3—H15	0.93 (2)	C14—H3	0.92 (3)
C4—C13	1.525 (2)	C14—H2	1.00 (2)
C4—H14	0.980 (18)	C14—H1	0.96 (3)
C4—H13	0.984 (19)
C8—O2—C11	115.99 (12)	O1—C8—O2	122.44 (13)
C9—N1—C14	109.43 (16)	O1—C8—C5	126.71 (12)
C9—N1—C3	109.83 (14)	O2—C8—C5	110.84 (11)
C14—N1—C3	109.95 (15)	N1—C9—C5	110.70 (12)
C10—C1—C7	119.32 (15)	N1—C9—H9	108.6 (9)
C10—C1—H18	120.4 (12)	C5—C9—H9	110.3 (10)
C7—C1—H18	120.3 (12)	N1—C9—H8	111.8 (10)
C10—C2—C6	119.14 (15)	C5—C9—H8	107.8 (10)
C10—C2—H17	121.6 (13)	H9—C9—H8	107.5 (14)
C6—C2—H17	119.2 (13)	C1—C10—C2	120.86 (15)
N1—C3—C4	111.63 (14)	C1—C10—Cl	119.10 (13)
N1—C3—H16	110.8 (12)	C2—C10—Cl	120.04 (13)
C4—C3—H16	110.5 (12)	O2—C11—H7	106.3 (15)
N1—C3—H15	108.5 (13)	O2—C11—H6	106.9 (15)
C4—C3—H15	110.9 (13)	H7—C11—H6	118 (2)
H16—C3—H15	104.3 (17)	O2—C11—H5	110.7 (15)
C3—C4—C13	110.64 (15)	H7—C11—H5	107 (2)
C3—C4—H14	109.1 (10)	H6—C11—H5	108 (2)
C13—C4—H14	108.8 (10)	C7—C12—C6	117.41 (14)
C3—C4—H13	109.2 (11)	C7—C12—C13	123.11 (13)
C13—C4—H13	109.9 (10)	C6—C12—C13	119.46 (13)
H14—C4—H13	109.1 (14)	C12—C13—C4	115.37 (12)
C8—C5—C9	111.16 (11)	C12—C13—C5	113.68 (12)
C8—C5—C13	113.57 (11)	C4—C13—C5	109.85 (12)
C9—C5—C13	109.44 (12)	C12—C13—H4	105.8 (10)
C8—C5—H12	106.4 (9)	C4—C13—H4	107.9 (9)
C9—C5—H12	106.9 (9)	C5—C13—H4	103.3 (9)
C13—C5—H12	109.1 (9)	N1—C14—H3	110.4 (17)
C2—C6—C12	121.65 (15)	N1—C14—H2	109.5 (14)
C2—C6—H11	119.9 (11)	H3—C14—H2	111 (2)
C12—C6—H11	118.5 (11)	N1—C14—H1	111.1 (14)
C1—C7—C12	121.61 (15)	H3—C14—H1	104 (2)
C1—C7—H10	118.6 (12)	H2—C14—H1	111.3 (19)
C12—C7—H10	119.8 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H12···O1^i	0.970 (12)	2.516 (17)	3.2518 (17)	132.7 (13)

Symmetry code: (i) x+1, y, z.