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Crystals of orthorhombic acet­amide, C2H5NO, were obtained from a mixture of ethyl­ acetate and dilute ammonia. The previously reported structure [Hamilton (1965). Acta Cryst. 18, 866–870] was confirmed, with two mol­ecules in the asymmetric unit. The mol­ecules are hydrogen bonded to form columns. Neighboring columns are connected by weak intermolecular C—H...O interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803019494/su6043sup1.cif
Contains datablocks default, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803019494/su6043Isup2.hkl
Contains datablock I

CCDC reference: 225718

Key indicators

  • Single-crystal X-ray study
  • T = 146 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.058
  • wR factor = 0.116
  • Data-to-parameter ratio = 19.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.99 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1996); software used to prepare material for publication: SHELXL97.

acetamide top
Crystal data top
C2H5NOF(000) = 512
Mr = 59.07Dx = 1.169 Mg m3
Orthorhombic, PccnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2acCell parameters from 213 reflections
a = 19.021 (4) Åθ = 3–26°
b = 7.5084 (14) ŵ = 0.09 mm1
c = 9.4038 (16) ÅT = 146 K
V = 1343.0 (4) Å3Rod, colorless
Z = 160.50 × 0.16 × 0.08 mm
Data collection top
SIEMENS_SMART_1K_CCD
diffractometer
1134 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tubeRint = 0.074
Graphite monochromatorθmax = 29.0°, θmin = 2.1°
ω scansh = 2623
12606 measured reflectionsk = 109
1767 independent reflectionsl = 1212
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: difference Fourier map
wR(F2) = 0.116H atoms treated by a mixture of independent and constrained refinement
S = 1.11 w = 1/[σ2(Fo2) + (0.05P)2]
where P = (Fo2 + 2Fc2)/3
1767 reflections(Δ/σ)max = 0.001
91 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.25 e Å3
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
O10.55232 (6)0.14563 (14)0.29156 (11)0.0318 (3)
N10.57489 (8)0.17989 (19)0.52416 (15)0.0298 (4)
C10.53372 (8)0.19720 (19)0.41127 (15)0.0252 (4)
C20.46294 (8)0.2816 (2)0.43387 (17)0.0338 (4)
H2A0.45750.38280.36890.054*
H2B0.45920.32330.53230.054*
H2C0.42600.19380.41510.054*
H010.6181 (10)0.134 (2)0.5123 (19)0.041 (5)*
H020.5617 (8)0.228 (3)0.604 (2)0.044 (5)*
O20.71375 (6)0.02080 (16)0.48261 (11)0.0377 (3)
N20.70150 (8)0.03422 (18)0.24500 (14)0.0315 (4)
C30.73947 (8)0.00898 (19)0.36143 (16)0.0265 (4)
C40.81577 (9)0.0366 (2)0.34175 (17)0.0359 (4)
H4A0.84490.06400.37240.057*
H4B0.82490.06190.24120.057*
H4C0.82740.14180.39890.057*
H030.6530 (10)0.058 (2)0.2564 (18)0.045 (5)*
H040.7234 (8)0.024 (2)0.1652 (18)0.035 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0333 (7)0.0419 (7)0.0202 (6)0.0015 (5)0.0009 (5)0.0004 (5)
N10.0289 (9)0.0404 (8)0.0202 (7)0.0042 (6)0.0015 (6)0.0021 (6)
C10.0290 (9)0.0237 (8)0.0229 (8)0.0030 (7)0.0034 (7)0.0035 (6)
C20.0291 (9)0.0352 (9)0.0372 (10)0.0039 (7)0.0002 (7)0.0005 (7)
O20.0305 (7)0.0606 (8)0.0221 (6)0.0069 (5)0.0009 (5)0.0019 (5)
N20.0251 (8)0.0489 (9)0.0204 (8)0.0012 (6)0.0011 (6)0.0005 (6)
C30.0268 (9)0.0284 (8)0.0242 (8)0.0005 (7)0.0003 (7)0.0021 (6)
C40.0277 (9)0.0446 (10)0.0353 (10)0.0017 (8)0.0008 (7)0.0021 (8)
Geometric parameters (Å, º) top
O1—C11.2419 (17)O2—C31.2433 (18)
N1—C11.326 (2)N2—C31.3253 (19)
N1—H010.898 (18)N2—H030.945 (19)
N1—H020.87 (2)N2—H040.862 (17)
C1—C21.503 (2)C3—C41.503 (2)
C2—H2A0.9800C4—H4A0.9800
C2—H2B0.9800C4—H4B0.9800
C2—H2C0.9800C4—H4C0.9800
C1—N1—H01118.6 (11)C3—N2—H03117.7 (11)
C1—N1—H02118.8 (11)C3—N2—H04116.3 (11)
H01—N1—H02121.9 (16)H03—N2—H04126.0 (15)
O1—C1—N1121.81 (15)O2—C3—N2122.17 (15)
O1—C1—C2120.98 (14)O2—C3—C4120.62 (14)
N1—C1—C2117.20 (14)N2—C3—C4117.21 (14)
C1—C2—H2A109.5C3—C4—H4A109.5
C1—C2—H2B109.5C3—C4—H4B109.5
H2A—C2—H2B109.5H4A—C4—H4B109.5
C1—C2—H2C109.5C3—C4—H4C109.5
H2A—C2—H2C109.5H4A—C4—H4C109.5
H2B—C2—H2C109.5H4B—C4—H4C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H01···O20.90 (2)2.03 (2)2.925 (2)177.6 (15)
N1—H02···O1i0.87 (2)2.01 (2)2.868 (2)168.1 (15)
N2—H03···O10.95 (2)2.05 (2)2.991 (2)171.6 (14)
N2—H04···O2ii0.86 (2)2.09 (2)2.949 (2)172.7 (14)
C2—H2A···O1iii0.982.493.471 (2)178
C4—H4B···O2ii0.982.623.451 (2)143
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+3/2, y, z1/2; (iii) x+1, y+1/2, z+1/2.
 

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