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In the title compound, C14H18N2O4·H2O, a potential antiamnesic agent, the morpholine ring adopts a symmetric chair conformation. The conformation of the mol­ecule in the crystal structure and that of the energy-minimized free mol­ecule do not differ significantly. In the crystalline state, the mol­ecules are stabilized by inter­molecular N—H...O, O—H...O and weak C—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680601289X/ci2046sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680601289X/ci2046Isup2.hkl
Contains datablock I

CCDC reference: 608587

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.042
  • wR factor = 0.119
  • Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.97
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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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), PLATON (Spek, 2003) and QMOL (Gans & Shalloway, 2001); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

N-[4-(Morpholinocarbonylmethoxy)phenyl]acetamide monohydrate top
Crystal data top
C14H18N2O4·H2OF(000) = 632
Mr = 296.32Dx = 1.336 Mg m3
Monoclinic, P21/nMelting point = 418–420 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 7.6438 (18) ÅCell parameters from 534 reflections
b = 17.170 (5) Åθ = 2.3–27.1°
c = 11.597 (3) ŵ = 0.10 mm1
β = 104.520 (7)°T = 298 K
V = 1473.4 (7) Å3Block, brown
Z = 40.4 × 0.4 × 0.3 mm
Data collection top
Bruker SMART CCD 1K area-detector
diffractometer
3024 independent reflections
Radiation source: fine-focus sealed tube2354 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
ω scansθmax = 26.4°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.927, Tmax = 1.000k = 2121
17319 measured reflectionsl = 1414
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.120 w = 1/[σ2(Fo2) + (0.0588P)2 + 0.2971P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
3024 reflectionsΔρmax = 0.21 e Å3
204 parametersΔρmin = 0.16 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.022 (2)
Special details top

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 (Å2) top
xyzUiso*/Ueq
N10.86700 (17)0.16751 (7)0.61189 (12)0.0456 (3)
H10.953 (3)0.1638 (10)0.6773 (17)0.062 (5)*
C10.80917 (18)0.09454 (8)0.55704 (12)0.0400 (3)
C20.7216 (2)0.08571 (9)0.43782 (13)0.0518 (4)
H20.69330.12930.38910.062*
C30.6764 (2)0.01229 (9)0.39123 (13)0.0523 (4)
H30.61730.00690.31110.063*
C40.71769 (19)0.05317 (8)0.46198 (13)0.0416 (3)
C50.8051 (2)0.04468 (9)0.58087 (13)0.0508 (4)
H50.83350.08830.62960.061*
C60.8503 (2)0.02899 (9)0.62720 (13)0.0505 (4)
H60.90960.03440.70730.061*
O10.66919 (15)0.12377 (6)0.40627 (9)0.0517 (3)
C70.7090 (2)0.19064 (8)0.47917 (13)0.0453 (4)
H7A0.83750.19280.51680.054*
H7B0.64420.18880.54110.054*
C80.65216 (19)0.26190 (8)0.40129 (13)0.0432 (3)
O20.58703 (17)0.25621 (6)0.29368 (10)0.0600 (3)
N20.68251 (17)0.33101 (7)0.45778 (11)0.0459 (3)
C90.6152 (2)0.40284 (9)0.39387 (15)0.0568 (4)
H9A0.49610.41480.40440.068*
H9B0.60470.39580.30940.068*
C100.7419 (3)0.46904 (10)0.44012 (17)0.0670 (5)
H10A0.85630.45960.42060.080*
H10B0.69160.51690.40090.080*
O40.77289 (17)0.47837 (7)0.56542 (11)0.0666 (4)
C110.8522 (2)0.40935 (10)0.62343 (16)0.0583 (4)
H11A0.87670.41640.70900.070*
H11B0.96650.40000.60370.070*
C120.7322 (2)0.34008 (10)0.58783 (14)0.0539 (4)
H12A0.79420.29360.62450.065*
H12B0.62370.34650.61590.065*
C130.8000 (2)0.23827 (8)0.57813 (14)0.0449 (3)
O30.67561 (16)0.24933 (6)0.48884 (11)0.0602 (3)
C140.8845 (3)0.30444 (9)0.65711 (17)0.0630 (5)
H14A0.80740.31920.70720.094*
H14B0.99990.28840.70570.094*
H14C0.90040.34800.60890.094*
O5W0.81975 (17)0.15111 (7)0.19445 (12)0.0566 (3)
H1W0.743 (4)0.1687 (16)0.228 (3)0.119 (10)*
H2W0.813 (3)0.1823 (14)0.132 (2)0.091 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0485 (7)0.0378 (7)0.0439 (7)0.0024 (5)0.0004 (6)0.0005 (5)
C10.0389 (7)0.0382 (7)0.0405 (7)0.0022 (6)0.0052 (6)0.0008 (6)
C20.0651 (10)0.0423 (8)0.0409 (8)0.0017 (7)0.0004 (7)0.0049 (6)
C30.0656 (10)0.0474 (9)0.0366 (8)0.0011 (7)0.0010 (7)0.0004 (6)
C40.0437 (8)0.0402 (8)0.0401 (7)0.0003 (6)0.0092 (6)0.0032 (6)
C50.0667 (10)0.0387 (8)0.0405 (8)0.0023 (7)0.0012 (7)0.0039 (6)
C60.0606 (9)0.0450 (8)0.0377 (8)0.0020 (7)0.0030 (7)0.0002 (6)
O10.0722 (7)0.0370 (6)0.0410 (6)0.0018 (5)0.0048 (5)0.0023 (4)
C70.0527 (8)0.0397 (8)0.0417 (8)0.0006 (6)0.0081 (6)0.0005 (6)
C80.0451 (8)0.0422 (8)0.0413 (8)0.0012 (6)0.0087 (6)0.0019 (6)
O20.0848 (9)0.0487 (6)0.0395 (6)0.0058 (6)0.0026 (5)0.0001 (5)
N20.0544 (7)0.0382 (6)0.0404 (6)0.0022 (5)0.0032 (5)0.0027 (5)
C90.0618 (10)0.0435 (9)0.0558 (10)0.0059 (7)0.0030 (8)0.0059 (7)
C100.0791 (12)0.0416 (9)0.0716 (12)0.0008 (8)0.0028 (9)0.0090 (8)
O40.0752 (8)0.0439 (6)0.0701 (8)0.0024 (5)0.0013 (6)0.0076 (5)
C110.0570 (10)0.0526 (9)0.0570 (10)0.0028 (7)0.0010 (8)0.0034 (8)
C120.0643 (10)0.0515 (9)0.0423 (8)0.0070 (7)0.0069 (7)0.0015 (7)
C130.0434 (8)0.0418 (8)0.0497 (8)0.0020 (6)0.0117 (7)0.0052 (6)
O30.0583 (7)0.0513 (6)0.0628 (7)0.0073 (5)0.0002 (6)0.0108 (5)
C140.0703 (11)0.0425 (9)0.0716 (12)0.0004 (8)0.0095 (9)0.0032 (8)
O5W0.0591 (7)0.0577 (7)0.0487 (7)0.0000 (6)0.0055 (6)0.0013 (6)
Geometric parameters (Å, º) top
N1—C131.3384 (19)N2—C121.4683 (19)
N1—C11.4244 (18)C9—C101.503 (2)
N1—H10.872 (19)C9—H9A0.97
C1—C61.378 (2)C9—H9B0.97
C1—C21.385 (2)C10—O41.422 (2)
C2—C31.381 (2)C10—H10A0.97
C2—H20.93C10—H10B0.97
C3—C41.381 (2)O4—C111.421 (2)
C3—H30.93C11—C121.496 (2)
C4—O11.3799 (16)C11—H11A0.97
C4—C51.381 (2)C11—H11B0.97
C5—C61.384 (2)C12—H12A0.97
C5—H50.93C12—H12B0.97
C6—H60.93C13—O31.2321 (18)
O1—C71.4129 (17)C13—C141.500 (2)
C7—C81.5182 (19)C14—H14A0.96
C7—H7A0.97C14—H14B0.96
C7—H7B0.97C14—H14C0.96
C8—O21.2260 (18)O5W—H1W0.84 (3)
C8—N21.3471 (18)O5W—H2W0.89 (3)
N2—C91.4643 (19)
C13—N1—C1127.93 (13)N2—C9—H9A109.6
C13—N1—H1118.1 (12)C10—C9—H9A109.6
C1—N1—H1113.9 (12)N2—C9—H9B109.6
C6—C1—C2118.79 (13)C10—C9—H9B109.6
C6—C1—N1117.09 (13)H9A—C9—H9B108.2
C2—C1—N1124.07 (13)O4—C10—C9112.16 (15)
C3—C2—C1120.09 (14)O4—C10—H10A109.2
C3—C2—H2120.0C9—C10—H10A109.2
C1—C2—H2120.0O4—C10—H10B109.2
C4—C3—C2120.87 (14)C9—C10—H10B109.2
C4—C3—H3119.6H10A—C10—H10B107.9
C2—C3—H3119.6C11—O4—C10109.37 (13)
O1—C4—C3116.25 (12)O4—C11—C12111.89 (13)
O1—C4—C5124.49 (13)O4—C11—H11A109.2
C3—C4—C5119.26 (13)C12—C11—H11A109.2
C4—C5—C6119.70 (13)O4—C11—H11B109.2
C4—C5—H5120.2C12—C11—H11B109.2
C6—C5—H5120.2H11A—C11—H11B107.9
C1—C6—C5121.29 (14)N2—C12—C11110.52 (13)
C1—C6—H6119.4N2—C12—H12A109.5
C5—C6—H6119.4C11—C12—H12A109.5
C4—O1—C7116.19 (11)N2—C12—H12B109.5
O1—C7—C8108.20 (11)C11—C12—H12B109.5
O1—C7—H7A110.1H12A—C12—H12B108.1
C8—C7—H7A110.1O3—C13—N1122.95 (14)
O1—C7—H7B110.1O3—C13—C14121.33 (14)
C8—C7—H7B110.1N1—C13—C14115.72 (14)
H7A—C7—H7B108.4C13—C14—H14A109.5
O2—C8—N2122.79 (13)C13—C14—H14B109.5
O2—C8—C7121.60 (13)H14A—C14—H14B109.5
N2—C8—C7115.59 (12)C13—C14—H14C109.5
C8—N2—C9120.00 (12)H14A—C14—H14C109.5
C8—N2—C12124.17 (12)H14B—C14—H14C109.5
C9—N2—C12113.46 (12)H1W—O5W—H2W105 (2)
N2—C9—C10110.06 (13)
C13—N1—C1—C6157.34 (15)O1—C7—C8—N2179.58 (12)
C13—N1—C1—C225.3 (2)O2—C8—N2—C98.3 (2)
C6—C1—C2—C30.3 (2)C7—C8—N2—C9173.38 (13)
N1—C1—C2—C3177.60 (14)O2—C8—N2—C12169.64 (15)
C1—C2—C3—C40.2 (3)C7—C8—N2—C1212.1 (2)
C2—C3—C4—O1178.98 (14)C8—N2—C9—C10147.40 (16)
C2—C3—C4—C50.1 (2)C12—N2—C9—C1049.4 (2)
O1—C4—C5—C6178.87 (15)N2—C9—C10—O455.0 (2)
C3—C4—C5—C60.2 (2)C9—C10—O4—C1160.78 (19)
C2—C1—C6—C50.3 (2)C10—O4—C11—C1260.67 (19)
N1—C1—C6—C5177.82 (15)C8—N2—C12—C11147.92 (15)
C4—C5—C6—C10.3 (3)C9—N2—C12—C1149.67 (19)
C3—C4—O1—C7179.06 (13)O4—C11—C12—N255.03 (19)
C5—C4—O1—C71.9 (2)C1—N1—C13—O31.8 (2)
C4—O1—C7—C8177.97 (12)C1—N1—C13—C14177.56 (14)
O1—C7—C8—O21.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O30.932.382.910 (2)116
O5W—H1W···O20.84 (3)2.17 (3)2.9617 (19)157 (3)
O5W—H2W···O3i0.89 (3)1.85 (3)2.7348 (19)174 (2)
N1—H1···O5Wii0.87 (2)2.00 (2)2.8566 (18)169 (2)
C10—H10B···O5Wi0.972.553.473 (2)159
Symmetry codes: (i) x+3/2, y+1/2, z+1/2; (ii) x+2, y, z+1.
 

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