(2S,3S)-3-Hydro­xy-1-(4-methoxy­benzyl)­piperidine-2-carbox­amide

The title compound, C₁₄H₂₀N₂O₃, has been obtained as an unexpected product when attempting to prepare (2S,3S)-3-hydroxy-1-(4-methoxy­benzyl)­piperidine-2-carboxyl­ic acid. The crystal structure involves intermolecular N—H...O and O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• R factor = 0.044
• wR factor = 0.124
• Data-to-parameter ratio = 7.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.76
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C14 H20 N2 O3

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           25.00
           From the CIF: _reflns_number_total               1335
           Count of symmetry unique reflns         1339
           Completeness (_total/calc)             99.70%
           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
   4 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 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
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and ViewerPro (Accelrys, 2001); software used to prepare material for publication: SHELXL97.

(2S,3S)-3-hydroxy-1-(4-methoxybenzyl)piperidine-2-carboxamide

Crystal data

C14H20N2O3	F(000) = 284
Mr = 264.32	Dx = 1.259 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4825 reflections
a = 6.0743 (13) Å	θ = 2.6–28.6°
b = 7.2436 (16) Å	µ = 0.09 mm^−1
c = 15.916 (3) Å	T = 293 K
β = 95.334 (4)°	Plate, colorless
V = 697.3 (3) Å^3	0.23 × 0.15 × 0.09 mm
Z = 2

Data collection

Bruker SMART APEX CCD diffractometer	1335 independent reflections
Radiation source: fine-focus sealed tube	1331 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −7→7
Tmin = 0.980, Tmax = 0.992	k = −8→8
6682 measured reflections	l = −18→18

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.124	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0647P)^2 + 0.3487P] where P = (Fo^2 + 2Fc^2)/3
1335 reflections	(Δ/σ)max = 0.006
172 parameters	Δρmax = 0.20 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
C1	−0.8321 (5)	−0.4697 (5)	−0.62285 (19)	0.0318 (7)
H1A	−0.9769	−0.4211	−0.6115	0.038*
C2	−0.8109 (5)	−0.6674 (5)	−0.5911 (2)	0.0348 (8)
H2A	−0.6640	−0.7145	−0.6006	0.042*
C3	−0.9825 (7)	−0.7881 (5)	−0.6364 (2)	0.0445 (9)
H3A	−1.1284	−0.7495	−0.6233	0.053*
H3B	−0.9603	−0.9150	−0.6181	0.053*
C4	−0.9666 (7)	−0.7747 (6)	−0.7297 (2)	0.0483 (10)
H4A	−1.0844	−0.8461	−0.7595	0.058*
H4B	−0.8264	−0.8250	−0.7435	0.058*
C5	−0.9851 (7)	−0.5760 (6)	−0.7569 (2)	0.0451 (9)
H5A	−0.9744	−0.5682	−0.8172	0.054*
H5B	−1.1286	−0.5284	−0.7455	0.054*
C6	−0.8261 (7)	−0.2768 (5)	−0.7445 (2)	0.0438 (9)
H6A	−0.7178	−0.2018	−0.7114	0.053*
H6B	−0.9714	−0.2272	−0.7372	0.053*
C7	−0.6535 (5)	−0.3552 (5)	−0.57586 (17)	0.0286 (7)
C8	−0.7855 (6)	−0.2641 (5)	−0.8358 (2)	0.0396 (8)
C9	−0.5966 (7)	−0.3329 (6)	−0.8636 (2)	0.0480 (9)
H9A	−0.4910	−0.3853	−0.8247	0.058*
C10	−0.5573 (6)	−0.3276 (6)	−0.9464 (2)	0.0477 (10)
H10A	−0.4269	−0.3764	−0.9634	0.057*
C11	−0.7107 (6)	−0.2500 (5)	−1.0047 (2)	0.0391 (8)
C12	−0.8994 (6)	−0.1768 (6)	−0.9776 (2)	0.0438 (9)
H12A	−1.0031	−0.1209	−1.0161	0.053*
C13	−0.9366 (6)	−0.1853 (5)	−0.8947 (2)	0.0427 (8)
H13A	−1.0670	−0.1367	−0.8776	0.051*
C14	−0.4992 (8)	−0.3102 (8)	−1.1187 (3)	0.0608 (12)
H14A	−0.5063	−0.2925	−1.1787	0.091*
H14B	−0.4883	−0.4396	−1.1062	0.091*
H14C	−0.3720	−0.2474	−1.0922	0.091*
N2	−0.7225 (5)	−0.2099 (4)	−0.53619 (17)	0.0388 (7)
H2B	−0.6286	−0.1391	−0.5083	0.047*
H2C	−0.8615	−0.1859	−0.5382	0.047*
O2	−0.4598 (3)	−0.3969 (4)	−0.57557 (14)	0.0401 (6)
O3	−0.8310 (4)	−0.6608 (4)	−0.50344 (13)	0.0384 (6)
H3C	−0.7425	−0.7327	−0.4790	0.058*
O4	−0.6915 (4)	−0.2383 (5)	−1.08810 (14)	0.0517 (7)
N1	−0.8132 (5)	−0.4640 (4)	−0.71323 (17)	0.0364 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0346 (16)	0.0333 (17)	0.0272 (15)	0.0048 (14)	0.0010 (12)	0.0012 (14)
C2	0.0335 (16)	0.039 (2)	0.0316 (15)	0.0039 (15)	0.0003 (12)	0.0054 (16)
C3	0.056 (2)	0.0336 (19)	0.0431 (19)	−0.0080 (17)	−0.0008 (15)	0.0061 (16)
C4	0.065 (2)	0.038 (2)	0.040 (2)	−0.0098 (19)	−0.0044 (16)	−0.0055 (17)
C5	0.059 (2)	0.044 (2)	0.0301 (17)	−0.0061 (19)	−0.0097 (15)	0.0014 (16)
C6	0.066 (2)	0.0326 (18)	0.0318 (18)	0.0006 (18)	−0.0003 (16)	−0.0023 (15)
C7	0.0332 (16)	0.0293 (17)	0.0229 (13)	−0.0019 (13)	0.0002 (11)	0.0030 (13)
C8	0.054 (2)	0.0282 (18)	0.0357 (17)	−0.0016 (16)	−0.0020 (14)	0.0018 (15)
C9	0.059 (2)	0.042 (2)	0.0402 (19)	0.0072 (19)	−0.0076 (16)	0.0091 (18)
C10	0.050 (2)	0.045 (2)	0.048 (2)	0.0102 (18)	0.0034 (16)	0.0035 (18)
C11	0.0458 (19)	0.0358 (19)	0.0346 (16)	−0.0069 (17)	−0.0015 (14)	0.0013 (16)
C12	0.0442 (18)	0.052 (2)	0.0328 (16)	−0.0006 (19)	−0.0074 (13)	0.0104 (17)
C13	0.0436 (18)	0.041 (2)	0.0437 (19)	0.0032 (17)	0.0022 (14)	0.0024 (17)
C14	0.073 (3)	0.065 (3)	0.046 (2)	0.008 (2)	0.016 (2)	0.002 (2)
N2	0.0342 (14)	0.0427 (18)	0.0386 (15)	−0.0039 (13)	−0.0015 (11)	−0.0088 (14)
O2	0.0283 (11)	0.0491 (15)	0.0418 (12)	−0.0010 (12)	−0.0038 (9)	−0.0073 (12)
O3	0.0414 (12)	0.0457 (14)	0.0277 (11)	0.0023 (11)	0.0003 (9)	0.0069 (11)
O4	0.0593 (15)	0.0624 (18)	0.0331 (12)	0.0048 (15)	0.0033 (11)	0.0053 (13)
N1	0.0477 (16)	0.0334 (15)	0.0266 (14)	−0.0024 (13)	−0.0039 (12)	0.0015 (13)

Geometric parameters (Å, º)

C1—N1	1.454 (4)	C7—O2	1.214 (4)
C1—C7	1.508 (4)	C7—N2	1.315 (4)
C1—C2	1.520 (5)	C8—C9	1.362 (6)
C1—H1A	0.9800	C8—C13	1.374 (5)
C2—O3	1.413 (4)	C9—C10	1.361 (5)
C2—C3	1.493 (5)	C9—H9A	0.9300
C2—H2A	0.9800	C10—C11	1.374 (5)
C3—C4	1.500 (5)	C10—H10A	0.9300
C3—H3A	0.9700	C11—O4	1.345 (4)
C3—H3B	0.9700	C11—C12	1.369 (5)
C4—C5	1.504 (6)	C12—C13	1.360 (5)
C4—H4A	0.9700	C12—H12A	0.9300
C4—H4B	0.9700	C13—H13A	0.9300
C5—N1	1.448 (5)	C14—O4	1.406 (5)
C5—H5A	0.9700	C14—H14A	0.9600
C5—H5B	0.9700	C14—H14B	0.9600
C6—N1	1.444 (5)	C14—H14C	0.9600
C6—C8	1.500 (5)	N2—H2B	0.8600
C6—H6A	0.9700	N2—H2C	0.8600
C6—H6B	0.9700	O3—H3C	0.8200
N1—C1—C7	110.8 (3)	O2—C7—N2	123.3 (3)
N1—C1—C2	110.1 (3)	O2—C7—C1	121.1 (3)
C7—C1—C2	108.6 (3)	N2—C7—C1	115.6 (3)
N1—C1—H1A	109.1	C9—C8—C13	117.4 (3)
C7—C1—H1A	109.1	C9—C8—C6	120.7 (3)
C2—C1—H1A	109.1	C13—C8—C6	121.8 (3)
O3—C2—C3	112.1 (3)	C10—C9—C8	122.2 (3)
O3—C2—C1	106.5 (3)	C10—C9—H9A	118.9
C3—C2—C1	110.9 (3)	C8—C9—H9A	118.9
O3—C2—H2A	109.1	C9—C10—C11	119.8 (4)
C3—C2—H2A	109.1	C9—C10—H10A	120.1
C1—C2—H2A	109.1	C11—C10—H10A	120.1
C2—C3—C4	109.5 (3)	O4—C11—C12	116.0 (3)
C2—C3—H3A	109.8	O4—C11—C10	125.2 (3)
C4—C3—H3A	109.8	C12—C11—C10	118.7 (3)
C2—C3—H3B	109.8	C13—C12—C11	120.5 (3)
C4—C3—H3B	109.8	C13—C12—H12A	119.7
H3A—C3—H3B	108.2	C11—C12—H12A	119.7
C3—C4—C5	109.7 (3)	C12—C13—C8	121.3 (3)
C3—C4—H4A	109.7	C12—C13—H13A	119.3
C5—C4—H4A	109.7	C8—C13—H13A	119.3
C3—C4—H4B	109.7	O4—C14—H14A	109.5
C5—C4—H4B	109.7	O4—C14—H14B	109.5
H4A—C4—H4B	108.2	H14A—C14—H14B	109.5
N1—C5—C4	111.5 (3)	O4—C14—H14C	109.5
N1—C5—H5A	109.3	H14A—C14—H14C	109.5
C4—C5—H5A	109.3	H14B—C14—H14C	109.5
N1—C5—H5B	109.3	C7—N2—H2B	120.0
C4—C5—H5B	109.3	C7—N2—H2C	120.0
H5A—C5—H5B	108.0	H2B—N2—H2C	120.0
N1—C6—C8	112.5 (3)	C2—O3—H3C	109.5
N1—C6—H6A	109.1	C11—O4—C14	118.0 (3)
C8—C6—H6A	109.1	C6—N1—C5	110.3 (3)
N1—C6—H6B	109.1	C6—N1—C1	111.2 (3)
C8—C6—H6B	109.1	C5—N1—C1	109.8 (3)
H6A—C6—H6B	107.8
N1—C1—C2—O3	−180.0 (2)	C9—C10—C11—O4	−179.3 (4)
C7—C1—C2—O3	58.5 (3)	C9—C10—C11—C12	1.0 (6)
N1—C1—C2—C3	−57.8 (4)	O4—C11—C12—C13	178.6 (4)
C7—C1—C2—C3	−179.3 (3)	C10—C11—C12—C13	−1.7 (6)
O3—C2—C3—C4	174.5 (3)	C11—C12—C13—C8	1.1 (6)
C1—C2—C3—C4	55.6 (4)	C9—C8—C13—C12	0.2 (6)
C2—C3—C4—C5	−55.4 (4)	C6—C8—C13—C12	−179.1 (4)
C3—C4—C5—N1	58.9 (5)	C12—C11—O4—C14	179.4 (4)
N1—C1—C7—O2	−65.0 (4)	C10—C11—O4—C14	−0.3 (6)
C2—C1—C7—O2	56.1 (4)	C8—C6—N1—C5	−63.4 (4)
N1—C1—C7—N2	115.0 (3)	C8—C6—N1—C1	174.5 (3)
C2—C1—C7—N2	−123.9 (3)	C4—C5—N1—C6	176.3 (3)
N1—C6—C8—C9	−55.6 (5)	C4—C5—N1—C1	−60.9 (4)
N1—C6—C8—C13	123.6 (4)	C7—C1—N1—C6	−58.1 (4)
C13—C8—C9—C10	−0.9 (6)	C2—C1—N1—C6	−178.2 (3)
C6—C8—C9—C10	178.4 (4)	C7—C1—N1—C5	179.5 (3)
C8—C9—C10—C11	0.3 (6)	C2—C1—N1—C5	59.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O2^i	0.86	2.24	3.027 (4)	153
N2—H2C···O3^ii	0.86	2.05	2.864 (4)	158
O3—H3C···O2^iii	0.82	1.87	2.686 (3)	180

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