Download citation
Download citation
link to html
In the title structure, C14H20NO3+·Cl, as expected, the pipiridine ring adopts a chair conformation and the carboxylic acid group and the benzene ring are essentially coplanar, forming a conjugated system. In the crystal structure, extended chains are formed through N—H...Cl and O—H...Cl hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805033520/lh6514sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805033520/lh6514Isup2.hkl
Contains datablock I

CCDC reference: 289801

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.032
  • wR factor = 0.073
  • Data-to-parameter ratio = 19.2

checkCIF/PLATON results

No syntax errors found



Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C14 H20 Cl1 N1 O3 Atom count from _chemical_formula_moiety:C14 H20 N1 O3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

1-[2-(4-Carboxyphenoxy)ethyl]piperidinium chloride top
Crystal data top
C14H20NO3+·ClDx = 1.310 Mg m3
Mr = 285.77Melting point: 277 K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ac 2abCell parameters from 20969 reflections
a = 16.777 (4) Åθ = 3.0–27.5°
b = 7.4464 (15) ŵ = 0.27 mm1
c = 23.192 (5) ÅT = 296 K
V = 2897.3 (11) Å3Block, colorless
Z = 80.30 × 0.20 × 0.20 mm
F(000) = 1216.00
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2190 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.036
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 2121
Tmin = 0.918, Tmax = 0.948k = 98
26060 measured reflectionsl = 3030
3317 independent reflections
Refinement top
Refinement on F2 w = 1/[0.0001Fo2 + σ(Fo2)]/(4Fo2)
R[F2 > 2σ(F2)] = 0.032(Δ/σ)max < 0.001
wR(F2) = 0.073Δρmax = 0.22 e Å3
S = 1.00Δρmin = 0.22 e Å3
3317 reflectionsExtinction correction: Larson (1970)
173 parametersExtinction coefficient: 438 (28)
H-atom parameters constrained
Special details top

Geometry. The geometry of the title compound is linear

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.60784 (2)0.15467 (5)0.188580 (10)0.04496 (9)
O10.72054 (6)0.28477 (16)0.54758 (4)0.0651 (3)
O20.61229 (6)0.45127 (13)0.56284 (4)0.0579 (3)
O30.64593 (6)0.61350 (12)0.29911 (4)0.0505 (2)
N10.60721 (6)0.57138 (14)0.17082 (4)0.0372 (2)
C10.67032 (9)0.38568 (19)0.52976 (6)0.0451 (4)
C20.66449 (8)0.44739 (17)0.46900 (6)0.0388 (3)
C30.72244 (9)0.39612 (18)0.43019 (6)0.0447 (4)
C40.71908 (9)0.44754 (19)0.37279 (6)0.0452 (4)
C50.65582 (9)0.55105 (17)0.35432 (6)0.0402 (3)
C60.59629 (9)0.60075 (19)0.39258 (6)0.0451 (4)
C70.60125 (9)0.55098 (18)0.44966 (6)0.0428 (3)
C80.70016 (8)0.5544 (2)0.25620 (6)0.0464 (4)
C90.68015 (9)0.6428 (2)0.19964 (6)0.0478 (4)
C100.61381 (10)0.5954 (2)0.10674 (6)0.0542 (4)
C110.54184 (11)0.5223 (2)0.07616 (6)0.0596 (5)
C120.46492 (11)0.6004 (2)0.09901 (6)0.0675 (5)
C130.46019 (9)0.5762 (2)0.16346 (6)0.0601 (4)
C140.53204 (9)0.6522 (2)0.19371 (6)0.0529 (4)
H30.76700.32190.44360.053*
H40.76070.41010.34570.054*
H60.55090.67140.37880.054*
H70.55990.58940.47680.051*
H820.75430.58400.26750.055*
H810.69530.42530.25170.055*
H1010.61810.72280.09850.065*
H1020.66120.53430.09300.065*
H1210.46380.72790.09040.081*
H1220.41980.54200.08070.081*
H1320.41230.63380.17780.072*
H1310.45790.44850.17160.072*
H1410.52790.63020.23480.064*
H1420.53380.78050.18670.064*
H910.72500.62940.17360.057*
H920.67120.76920.20720.057*
H1120.54610.54860.03530.072*
H1110.54040.39320.08180.071*
H2010.61910.42200.60140.070*
H2220.60520.45800.17780.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0478 (2)0.04361 (19)0.04346 (19)0.00131 (18)0.00013 (16)0.00247 (14)
O10.0619 (7)0.0771 (7)0.0563 (6)0.0199 (6)0.0085 (5)0.0112 (5)
O20.0637 (7)0.0634 (6)0.0467 (5)0.0107 (6)0.0057 (5)0.0098 (5)
O30.0536 (6)0.0571 (6)0.0409 (5)0.0143 (5)0.0003 (4)0.0022 (4)
N10.0386 (6)0.0362 (5)0.0367 (5)0.0035 (5)0.0010 (5)0.0013 (4)
C10.0444 (8)0.0415 (8)0.0493 (8)0.0037 (7)0.0050 (7)0.0004 (6)
C20.0368 (7)0.0339 (6)0.0458 (7)0.0036 (6)0.0047 (6)0.0015 (6)
C30.0420 (8)0.0424 (7)0.0496 (8)0.0084 (6)0.0071 (6)0.0007 (6)
C40.0410 (8)0.0485 (8)0.0460 (7)0.0084 (7)0.0005 (6)0.0061 (6)
C50.0416 (8)0.0360 (6)0.0429 (7)0.0001 (6)0.0050 (6)0.0014 (6)
C60.0397 (8)0.0444 (8)0.0511 (8)0.0105 (6)0.0027 (6)0.0034 (6)
C70.0390 (8)0.0414 (7)0.0479 (7)0.0029 (6)0.0041 (6)0.0001 (6)
C80.0373 (8)0.0564 (8)0.0455 (7)0.0008 (7)0.0033 (6)0.0052 (7)
C90.0403 (8)0.0567 (9)0.0463 (8)0.0121 (7)0.0013 (6)0.0004 (7)
C100.0607 (10)0.0632 (10)0.0386 (7)0.0084 (8)0.0025 (7)0.0089 (6)
C110.0675 (11)0.0731 (11)0.0380 (8)0.0062 (9)0.0093 (7)0.0045 (7)
C120.0648 (11)0.0633 (11)0.0745 (11)0.0120 (9)0.0287 (9)0.0023 (8)
C130.0379 (8)0.0723 (10)0.0699 (10)0.0092 (8)0.0043 (7)0.0187 (9)
C140.0442 (9)0.0567 (9)0.0579 (9)0.0029 (8)0.0019 (7)0.0167 (7)
Geometric parameters (Å, º) top
O1—C11.2022 (18)N1—H2220.860
O2—C11.3323 (18)C3—H30.980
O3—C51.3723 (16)C4—H40.980
O3—C81.4184 (16)C6—H60.980
N1—C91.4922 (18)C7—H70.980
N1—C101.5010 (16)C8—H820.970
N1—C141.4947 (18)C8—H810.970
C1—C21.4854 (19)C9—H910.970
C2—C31.3788 (19)C9—H920.970
C2—C71.3863 (19)C10—H1010.970
C3—C41.3863 (19)C10—H1020.970
C4—C51.380 (2)C11—H1120.970
C5—C61.386 (2)C11—H1110.970
C6—C71.3772 (19)C12—H1210.970
C8—C91.505 (2)C12—H1220.970
C10—C111.502 (2)C13—H1320.970
C11—C121.511 (2)C13—H1310.970
C12—C131.508 (2)C14—H1410.970
C13—C141.505 (2)C14—H1420.970
O2—H2010.928
Cl1···O23.0219 (9)H7···H33.468
Cl1···N13.1302 (11)H7···H72.639
Cl1···C93.5672 (15)H7···H1013.298
O1···C13.5150 (18)H7···H1213.375
O1···C103.2252 (19)H7···H1213.137
O2···Cl13.0219 (9)H7···H1123.026
O2···C73.5942 (19)H7···H1113.130
O2···C103.5260 (19)H7···H2013.510
N1···Cl13.1302 (11)H82···Cl12.996
C1···O13.5150 (18)H82···C83.594
C7···O23.5942 (19)H82···H43.041
C9···Cl13.5672 (15)H82···H812.703
C10···O13.2252 (19)H82···H1322.962
C10···O23.5260 (19)H82···H923.002
Cl1···H63.089H81···Cl12.891
Cl1···H822.996H81···C83.274
Cl1···H812.891H81···C93.202
Cl1···H1323.120H81···H822.703
Cl1···H1313.358H81···H1323.262
Cl1···H1412.894H81···H913.151
Cl1···H1423.050H81···H922.727
Cl1···H912.832H101···O12.954
Cl1···H923.091H101···O22.566
Cl1···H1113.252H101···C13.437
Cl1···H2012.109H101···H73.298
Cl1···H2222.273H101···H2012.646
O1···H1012.954H102···O12.783
O1···H1022.783H102···O12.619
O1···H1022.619H102···C13.457
O1···H913.128H102···C13.239
O1···H1113.394H102···H2013.476
O2···H63.188H121···O23.511
O2···H73.047H121···C23.033
O2···H1012.566H121···C33.400
O2···H1213.511H121···C43.580
O2···H1112.869H121···C53.385
O3···H42.915H121···C62.980
O3···H1313.117H121···C72.801
C1···H1013.437H121···H63.388
C1···H1023.457H121···H73.375
C1···H1023.239H121···H73.137
C1···H1113.244H121···H1123.573
C2···H33.074H122···C23.528
C2···H1213.033H122···C33.566
C2···H1223.528H122···C33.495
C3···H33.191H122···C63.355
C3···H1213.400H122···H33.095
C3···H1223.566H122···H43.318
C3···H1223.495H122···H62.956
C4···H33.243H122···H1122.833
C4···H43.518H132···Cl13.120
C4···H1213.580H132···C43.420
C4···H1323.420H132···C53.393
C5···H33.167H132···H43.599
C5···H43.026H132···H43.089
C5···H1213.385H132···H822.962
C5···H1323.393H132···H813.262
C5···H1313.572H131···Cl13.358
C6···H33.061H131···O33.117
C6···H43.500H131···C53.572
C6···H1212.980H131···C63.123
C6···H1223.355H131···H43.345
C6···H1313.123H131···H62.376
C6···H1113.218H131···H1413.222
C7···H32.996H131···H1423.519
C7···H73.363H141···Cl12.894
C7···H1212.801H141···H1313.222
C7···H1113.560H141···H1423.341
C8···H43.428H142···Cl13.050
C8···H823.594H142···H63.577
C8···H813.274H142···H1313.519
C8···H923.234H142···H1413.341
C9···H813.202H142···H2013.296
C10···H2013.597H91···Cl12.832
C11···H63.215H91···O13.128
C11···H1123.024H91···H813.151
C12···H63.246H91···H923.292
C12···H1123.312H91···H2013.128
C13···H43.575H92···Cl13.091
C13···H63.175H92···C83.234
H3···C23.074H92···H43.566
H3···C33.191H92···H823.002
H3···C43.243H92···H812.727
H3···C53.167H92···H913.292
H3···C63.061H92···H2013.474
H3···C72.996H112···C113.024
H3···H63.585H112···C123.312
H3···H73.468H112···H73.026
H3···H1223.095H112···H1213.573
H4···O32.915H112···H1222.833
H4···C43.518H112···H1122.367
H4···C53.026H112···H1113.109
H4···C63.500H111···Cl13.252
H4···C83.428H111···O13.394
H4···C133.575H111···O22.869
H4···H823.041H111···C13.244
H4···H1223.318H111···C63.218
H4···H1323.599H111···C73.560
H4···H1323.089H111···H62.431
H4···H1313.345H111···H73.130
H4···H923.566H111···H1123.109
H6···Cl13.089H111···H2012.732
H6···O23.188H201···Cl12.109
H6···C113.215H201···C103.597
H6···C123.246H201···H62.971
H6···C133.175H201···H73.510
H6···H33.585H201···H1012.646
H6···H1213.388H201···H1023.476
H6···H1222.956H201···H1423.296
H6···H1312.376H201···H913.128
H6···H1423.577H201···H923.474
H6···H1112.431H201···H1112.732
H6···H2012.971H201···H2223.346
H7···O23.047H222···Cl12.273
H7···C73.363H222···H2013.346
C5—O3—C8118.16 (10)O3—C8—H82109.9
C9—N1—C10109.91 (10)O3—C8—H81109.2
C9—N1—C14112.92 (10)C9—C8—H82110.1
C10—N1—C14111.47 (10)C9—C8—H81108.7
O1—C1—O2122.91 (12)H82—C8—H81109.5
O1—C1—C2124.45 (13)N1—C9—H91108.7
O2—C1—C2112.63 (11)N1—C9—H92107.4
C1—C2—C3119.16 (12)C8—C9—H91108.9
C1—C2—C7121.97 (12)C8—C9—H92107.5
C3—C2—C7118.85 (12)H91—C9—H92109.5
C2—C3—C4121.45 (13)N1—C10—H101108.4
C3—C4—C5118.92 (13)N1—C10—H102109.3
O3—C5—C4124.89 (12)C11—C10—H101108.7
O3—C5—C6114.81 (12)C11—C10—H102109.4
C4—C5—C6120.30 (12)H101—C10—H102109.5
C5—C6—C7119.99 (13)C10—C11—H112109.2
C2—C7—C6120.46 (13)C10—C11—H111108.4
O3—C8—C9109.43 (11)C12—C11—H112109.1
N1—C9—C8114.67 (11)C12—C11—H111108.2
N1—C10—C11111.41 (12)H112—C11—H111109.5
C10—C11—C12112.41 (13)C11—C12—H121108.7
C11—C12—C13110.28 (13)C11—C12—H122109.9
C12—C13—C14112.03 (13)C13—C12—H121108.7
N1—C14—C13111.03 (11)C13—C12—H122109.8
C1—O2—H201112.3H121—C12—H122109.5
C9—N1—H222107.3C12—C13—H132109.4
C10—N1—H222107.8C12—C13—H131108.2
C14—N1—H222107.2C14—C13—H132109.7
C2—C3—H3119.2C14—C13—H131108.0
C4—C3—H3119.4H132—C13—H131109.5
C3—C4—H4120.6N1—C14—H141110.0
C5—C4—H4120.5N1—C14—H142108.1
C5—C6—H6119.6C13—C14—H141109.7
C7—C6—H6120.4C13—C14—H142108.5
C2—C7—H7119.7H141—C14—H142109.5
C6—C7—H7119.8
C5—O3—C8—C9178.32 (11)C1—C2—C7—C6177.76 (13)
C8—O3—C5—C46.33 (19)C3—C2—C7—C60.4 (2)
C8—O3—C5—C6174.09 (11)C7—C2—C3—C40.7 (2)
C9—N1—C10—C11179.12 (12)C2—C3—C4—C50.5 (2)
C10—N1—C9—C8152.26 (12)C3—C4—C5—O3178.84 (12)
C9—N1—C14—C13179.95 (11)C3—C4—C5—C60.7 (2)
C14—N1—C9—C882.59 (14)O3—C5—C6—C7177.81 (12)
C10—N1—C14—C1355.74 (15)C4—C5—C6—C71.8 (2)
C14—N1—C10—C1154.90 (16)C5—C6—C7—C21.6 (2)
O1—C1—C2—C34.0 (2)O3—C8—C9—N173.73 (14)
O1—C1—C2—C7174.10 (14)N1—C10—C11—C1254.20 (17)
O2—C1—C2—C3177.40 (12)C10—C11—C12—C1353.60 (18)
O2—C1—C2—C74.47 (18)C11—C12—C13—C1454.44 (18)
C1—C2—C3—C4178.91 (12)C12—C13—C14—N156.07 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H201···Cl1i0.932.113.0219 (9)168
N1—H222···Cl10.862.273.1302 (11)174
Symmetry code: (i) x, y+1/2, z+1/2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds