1-Methyl­piperidin-4-yl hydroxy­diphenyl­acetate

The title compound, C₂₀H₂₃NO₃, is a metabolite and an important inter­mediate in the synthesis of propiverine hydro­chloride. The crystal packing is stabilized by inter­molecular O—H...N and C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 113 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.043
• wR factor = 0.109
• Data-to-parameter ratio = 18.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT737_ALERT_1_C D...A   Calc  3.4096(14), Rep    3.410(3) ......       2.14 su-Ra
              C5   -O2      1.555   8.557
PLAT745_ALERT_1_C D-H     Calc   0.908(18), Rep     0.90800 ......    Missing su
              O1   -H1      1.555   1.555
PLAT746_ALERT_1_C H...A   Calc   1.903(17), Rep     1.90200 ......    Missing su
              H1   -N1      1.555   4.554

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

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

---

Computing details

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalStructure (Rigaku/MSC, 2005); software used to prepare material for publication: CrystalStructure.

1-Methylpiperidin-4-yl hydroxydiphenylacetate

Crystal data

C20H23NO3	Dx = 1.243 Mg m^−3
Mr = 325.39	Melting point = 432–433 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71070 Å
a = 15.3791 (17) Å	Cell parameters from 8889 reflections
b = 13.2941 (14) Å	θ = 1.8–27.9°
c = 17.0078 (19) Å	µ = 0.08 mm^−1
V = 3477.3 (7) Å^3	T = 113 K
Z = 8	Block, colorless
F(000) = 1392	0.32 × 0.22 × 0.14 mm

Data collection

Rigaku Saturn diffractometer	4139 independent reflections
Radiation source: rotating anode	3419 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.044
Detector resolution: 7.31 pixels mm^-1	θmax = 27.9°, θmin = 2.4°
ω scans	h = −20→20
Absorption correction: multi-scan (Jacobson, 1998)	k = −17→10
Tmin = 0.970, Tmax = 0.989	l = −22→22
30893 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.109	w = 1/[σ^2(Fo^2) + (0.0599P)^2 + 0.15P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.001
4139 reflections	Δρmax = 0.31 e Å^−3
223 parameters	Δρmin = −0.22 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0133 (13)

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	0.19730 (5)	0.09183 (6)	0.55220 (5)	0.0182 (2)
O2	0.32242 (5)	0.04368 (7)	0.65787 (5)	0.0254 (2)
O3	0.22350 (5)	−0.00933 (7)	0.74601 (5)	0.0232 (2)
N1	0.19352 (6)	0.00817 (8)	0.94817 (6)	0.0209 (2)
C1	0.16862 (7)	0.04632 (8)	0.62280 (6)	0.0159 (2)
C2	0.24833 (7)	0.02823 (8)	0.67675 (7)	0.0178 (2)
C3	0.10768 (7)	0.12141 (8)	0.66371 (7)	0.0166 (2)
C4	0.05196 (7)	0.09108 (9)	0.72402 (7)	0.0195 (3)
H4	0.0505	0.0224	0.7395	0.023*
C5	−0.00138 (7)	0.16041 (9)	0.76163 (7)	0.0229 (3)
H5	−0.0392	0.1389	0.8025	0.027*
C6	0.00037 (8)	0.26062 (10)	0.73974 (8)	0.0253 (3)
H6	−0.0358	0.3081	0.7657	0.030*
C7	0.05534 (8)	0.29139 (9)	0.67970 (8)	0.0262 (3)
H7	0.0566	0.3601	0.6643	0.031*
C8	0.10861 (7)	0.22203 (9)	0.64194 (7)	0.0208 (3)
H8	0.1460	0.2437	0.6008	0.025*
C9	0.12578 (7)	−0.05451 (8)	0.60359 (6)	0.0159 (2)
C10	0.03956 (7)	−0.05741 (9)	0.57778 (7)	0.0188 (3)
H10	0.0052	0.0020	0.5795	0.023*
C11	0.00356 (8)	−0.14601 (9)	0.54963 (7)	0.0221 (3)
H11	−0.0550	−0.1470	0.5320	0.026*
C12	0.05292 (8)	−0.23304 (9)	0.54725 (7)	0.0235 (3)
H12	0.0284	−0.2935	0.5274	0.028*
C13	0.13827 (8)	−0.23194 (9)	0.57384 (7)	0.0239 (3)
H13	0.1721	−0.2918	0.5729	0.029*
C14	0.17398 (7)	−0.14299 (9)	0.60184 (7)	0.0202 (3)
H14	0.2324	−0.1425	0.6201	0.024*
C15	0.29088 (8)	−0.03155 (10)	0.80476 (7)	0.0262 (3)
H15	0.3458	−0.0538	0.7785	0.031*
C16	0.30702 (8)	0.06142 (11)	0.85422 (8)	0.0281 (3)
H16A	0.3251	0.1176	0.8197	0.034*
H16B	0.3549	0.0480	0.8916	0.034*
C17	0.22593 (8)	0.09166 (9)	0.89959 (7)	0.0238 (3)
H17A	0.2395	0.1499	0.9338	0.029*
H17B	0.1801	0.1125	0.8621	0.029*
C18	0.17393 (8)	−0.08022 (9)	0.89909 (7)	0.0251 (3)
H18A	0.1272	−0.0630	0.8614	0.030*
H18B	0.1526	−0.1356	0.9329	0.030*
C19	0.25370 (9)	−0.11530 (10)	0.85416 (7)	0.0297 (3)
H19A	0.2983	−0.1390	0.8918	0.036*
H19B	0.2377	−0.1725	0.8198	0.036*
C20	0.11455 (8)	0.03935 (12)	0.98938 (8)	0.0330 (3)
H20A	0.1273	0.0979	1.0224	0.040*
H20B	0.0937	−0.0160	1.0224	0.040*
H20C	0.0696	0.0571	0.9509	0.040*
H1	0.2300 (11)	0.0472 (14)	0.5247 (10)	0.055 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0201 (4)	0.0196 (4)	0.0148 (4)	0.0008 (3)	0.0042 (3)	0.0015 (3)
O2	0.0164 (4)	0.0350 (5)	0.0248 (5)	−0.0028 (4)	−0.0010 (3)	0.0009 (4)
O3	0.0191 (4)	0.0358 (5)	0.0148 (4)	0.0035 (4)	−0.0015 (3)	0.0038 (4)
N1	0.0200 (5)	0.0266 (6)	0.0161 (5)	0.0022 (4)	−0.0011 (4)	0.0007 (4)
C1	0.0163 (5)	0.0185 (6)	0.0129 (5)	0.0000 (4)	0.0016 (4)	0.0011 (4)
C2	0.0188 (5)	0.0183 (5)	0.0164 (5)	0.0001 (5)	0.0000 (4)	−0.0029 (5)
C3	0.0154 (5)	0.0192 (6)	0.0152 (6)	−0.0004 (4)	−0.0021 (4)	−0.0023 (5)
C4	0.0197 (6)	0.0202 (6)	0.0187 (6)	−0.0005 (5)	0.0007 (4)	−0.0001 (5)
C5	0.0193 (6)	0.0294 (7)	0.0199 (6)	−0.0010 (5)	0.0037 (4)	−0.0038 (5)
C6	0.0241 (6)	0.0254 (6)	0.0262 (7)	0.0049 (5)	0.0037 (5)	−0.0077 (5)
C7	0.0304 (7)	0.0183 (6)	0.0299 (7)	0.0013 (5)	0.0016 (5)	−0.0029 (5)
C8	0.0212 (6)	0.0205 (6)	0.0207 (6)	−0.0021 (5)	0.0021 (4)	−0.0004 (5)
C9	0.0183 (5)	0.0178 (6)	0.0117 (5)	−0.0003 (4)	0.0013 (4)	0.0008 (4)
C10	0.0188 (5)	0.0197 (6)	0.0180 (6)	0.0022 (4)	−0.0003 (4)	0.0009 (5)
C11	0.0195 (6)	0.0255 (6)	0.0212 (6)	−0.0032 (5)	−0.0013 (4)	−0.0008 (5)
C12	0.0278 (6)	0.0193 (6)	0.0233 (6)	−0.0048 (5)	0.0015 (5)	−0.0025 (5)
C13	0.0278 (6)	0.0190 (6)	0.0248 (6)	0.0034 (5)	0.0023 (5)	0.0000 (5)
C14	0.0170 (5)	0.0228 (6)	0.0206 (6)	0.0026 (5)	−0.0002 (4)	0.0004 (5)
C15	0.0204 (6)	0.0420 (8)	0.0163 (6)	0.0104 (5)	−0.0035 (4)	0.0010 (6)
C16	0.0203 (6)	0.0419 (8)	0.0221 (7)	−0.0063 (5)	−0.0039 (5)	0.0043 (6)
C17	0.0282 (6)	0.0230 (6)	0.0202 (6)	−0.0015 (5)	−0.0043 (5)	0.0011 (5)
C18	0.0307 (7)	0.0251 (6)	0.0196 (6)	−0.0058 (5)	−0.0052 (5)	0.0053 (5)
C19	0.0423 (8)	0.0261 (7)	0.0207 (6)	0.0106 (6)	−0.0088 (6)	−0.0019 (5)
C20	0.0236 (6)	0.0514 (9)	0.0241 (7)	0.0103 (6)	0.0012 (5)	0.0022 (6)

Geometric parameters (Å, º)

O1—C1	1.4151 (13)	C10—H10	0.9500
O1—H1	0.908 (19)	C11—C12	1.3845 (17)
O2—C2	1.2015 (13)	C11—H11	0.9500
O3—C2	1.3352 (14)	C12—C13	1.3884 (17)
O3—C15	1.4695 (14)	C12—H12	0.9500
N1—C20	1.4622 (15)	C13—C14	1.3880 (16)
N1—C17	1.4706 (15)	C13—H13	0.9500
N1—C18	1.4725 (15)	C14—H14	0.9500
C1—C9	1.5289 (15)	C15—C19	1.5075 (19)
C1—C3	1.5359 (15)	C15—C16	1.5155 (19)
C1—C2	1.5499 (15)	C15—H15	1.0000
C3—C8	1.3881 (16)	C16—C17	1.5206 (17)
C3—C4	1.3960 (15)	C16—H16A	0.9900
C4—C5	1.3898 (16)	C16—H16B	0.9900
C4—H4	0.9500	C17—H17A	0.9900
C5—C6	1.3836 (18)	C17—H17B	0.9900
C5—H5	0.9500	C18—C19	1.5187 (18)
C6—C7	1.3874 (18)	C18—H18A	0.9900
C6—H6	0.9500	C18—H18B	0.9900
C7—C8	1.3907 (16)	C19—H19A	0.9900
C7—H7	0.9500	C19—H19B	0.9900
C8—H8	0.9500	C20—H20A	0.9800
C9—C14	1.3908 (16)	C20—H20B	0.9800
C9—C10	1.3972 (15)	C20—H20C	0.9800
C10—C11	1.3868 (16)
C1—O1—H1	109.3 (11)	C13—C12—H12	120.0
C2—O3—C15	118.26 (9)	C14—C13—C12	119.66 (11)
C20—N1—C17	109.69 (10)	C14—C13—H13	120.2
C20—N1—C18	109.15 (10)	C12—C13—H13	120.2
C17—N1—C18	110.68 (9)	C13—C14—C9	121.13 (11)
O1—C1—C9	109.14 (9)	C13—C14—H14	119.4
O1—C1—C3	107.26 (9)	C9—C14—H14	119.4
C9—C1—C3	113.80 (9)	O3—C15—C19	105.07 (10)
O1—C1—C2	108.80 (8)	O3—C15—C16	109.21 (10)
C9—C1—C2	109.35 (9)	C19—C15—C16	110.80 (10)
C3—C1—C2	108.38 (9)	O3—C15—H15	110.5
O2—C2—O3	124.81 (10)	C19—C15—H15	110.5
O2—C2—C1	124.43 (10)	C16—C15—H15	110.5
O3—C2—C1	110.74 (9)	C15—C16—C17	111.28 (10)
C8—C3—C4	118.73 (10)	C15—C16—H16A	109.4
C8—C3—C1	119.95 (10)	C17—C16—H16A	109.4
C4—C3—C1	121.31 (10)	C15—C16—H16B	109.4
C5—C4—C3	120.60 (11)	C17—C16—H16B	109.4
C5—C4—H4	119.7	H16A—C16—H16B	108.0
C3—C4—H4	119.7	N1—C17—C16	111.32 (10)
C6—C5—C4	120.21 (11)	N1—C17—H17A	109.4
C6—C5—H5	119.9	C16—C17—H17A	109.4
C4—C5—H5	119.9	N1—C17—H17B	109.4
C5—C6—C7	119.59 (11)	C16—C17—H17B	109.4
C5—C6—H6	120.2	H17A—C17—H17B	108.0
C7—C6—H6	120.2	N1—C18—C19	111.41 (10)
C6—C7—C8	120.23 (12)	N1—C18—H18A	109.3
C6—C7—H7	119.9	C19—C18—H18A	109.3
C8—C7—H7	119.9	N1—C18—H18B	109.3
C3—C8—C7	120.64 (11)	C19—C18—H18B	109.3
C3—C8—H8	119.7	H18A—C18—H18B	108.0
C7—C8—H8	119.7	C15—C19—C18	111.09 (10)
C14—C9—C10	118.41 (10)	C15—C19—H19A	109.4
C14—C9—C1	121.09 (10)	C18—C19—H19A	109.4
C10—C9—C1	120.02 (10)	C15—C19—H19B	109.4
C11—C10—C9	120.72 (11)	C18—C19—H19B	109.4
C11—C10—H10	119.6	H19A—C19—H19B	108.0
C9—C10—H10	119.6	N1—C20—H20A	109.5
C12—C11—C10	120.06 (11)	N1—C20—H20B	109.5
C12—C11—H11	120.0	H20A—C20—H20B	109.5
C10—C11—H11	120.0	N1—C20—H20C	109.5
C11—C12—C13	120.00 (11)	H20A—C20—H20C	109.5
C11—C12—H12	120.0	H20B—C20—H20C	109.5
C15—O3—C2—O2	1.52 (17)	C2—C1—C9—C14	−28.34 (14)
C15—O3—C2—C1	179.82 (9)	O1—C1—C9—C10	−81.34 (12)
O1—C1—C2—O2	−5.30 (15)	C3—C1—C9—C10	38.42 (14)
C9—C1—C2—O2	113.81 (12)	C2—C1—C9—C10	159.75 (10)
C3—C1—C2—O2	−121.62 (12)	C14—C9—C10—C11	−1.27 (17)
O1—C1—C2—O3	176.39 (9)	C1—C9—C10—C11	170.86 (10)
C9—C1—C2—O3	−64.50 (11)	C9—C10—C11—C12	0.35 (18)
C3—C1—C2—O3	60.07 (12)	C10—C11—C12—C13	0.69 (18)
O1—C1—C3—C8	−17.37 (13)	C11—C12—C13—C14	−0.79 (18)
C9—C1—C3—C8	−138.18 (10)	C12—C13—C14—C9	−0.16 (18)
C2—C1—C3—C8	99.94 (12)	C10—C9—C14—C13	1.17 (17)
O1—C1—C3—C4	163.94 (10)	C1—C9—C14—C13	−170.86 (10)
C9—C1—C3—C4	43.13 (14)	C2—O3—C15—C19	−152.33 (10)
C2—C1—C3—C4	−78.75 (12)	C2—O3—C15—C16	88.77 (12)
C8—C3—C4—C5	−0.16 (17)	O3—C15—C16—C17	62.54 (13)
C1—C3—C4—C5	178.55 (10)	C19—C15—C16—C17	−52.73 (13)
C3—C4—C5—C6	−0.16 (18)	C20—N1—C17—C16	−178.69 (10)
C4—C5—C6—C7	0.36 (18)	C18—N1—C17—C16	−58.20 (12)
C5—C6—C7—C8	−0.24 (19)	C15—C16—C17—N1	55.54 (13)
C4—C3—C8—C7	0.28 (17)	C20—N1—C18—C19	179.44 (10)
C1—C3—C8—C7	−178.45 (10)	C17—N1—C18—C19	58.62 (12)
C6—C7—C8—C3	−0.08 (18)	O3—C15—C19—C18	−64.86 (12)
O1—C1—C9—C14	90.56 (12)	C16—C15—C19—C18	52.97 (13)
C3—C1—C9—C14	−149.68 (10)	N1—C18—C19—C15	−56.26 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1^i	0.908	1.902	2.7780 (13)	161.4
C5—H5···O2^ii	0.95	2.57	3.410 (3)	148

Symmetry codes: (i) −x+1/2, −y, z−1/2; (ii) x−1/2, y, −z+3/2.