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At 294 K, the C=C(H)—C=O grouping and the imidazoline ring of the title compound, C11H11ClN2O, are coplanar as a result of an intra­molecular N—H...O hydrogen bond and the conjugation, while the 4-chloro­phenyl ring is twisted from the plane by 23.5 (2)°. Inter­molecular N—H...O hydrogen bonding helps to establish the crystal packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806019805/hb2059sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806019805/hb2059Isup2.hkl
Contains datablock I

CCDC reference: 613689

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.036
  • wR factor = 0.095
  • Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry ..... 80 PerFit
Alert level C STRVA01_ALERT_4_C Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.350 From the CIF: _refine_ls_abs_structure_Flack_su 0.090 PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... 0.35 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for N2 PLAT352_ALERT_3_C Short N-H Bond (0.87A) N1 - H1 ... 0.74 Ang.
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 26.54 From the CIF: _reflns_number_total 1996 Count of symmetry unique reflns 1192 Completeness (_total/calc) 167.45% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 804 Fraction of Friedel pairs measured 0.674 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 6 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 3 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 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXTL.

1-(4-Chlorophenyl)-2-(imidazolidin-2-ylidene)ethanone top
Crystal data top
C11H11ClN2ODx = 1.397 Mg m3
Mr = 222.67Melting point: 511 K
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 6.5657 (17) ÅCell parameters from 1409 reflections
b = 6.976 (2) Åθ = 3.1–26.2°
c = 11.602 (3) ŵ = 0.33 mm1
β = 94.981 (4)°T = 294 K
V = 529.4 (2) Å3Prism, colorless
Z = 20.24 × 0.18 × 0.16 mm
F(000) = 232
Data collection top
Bruker SMART CCD
diffractometer
1996 independent reflections
Radiation source: fine-focus sealed tube1676 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
ω scansθmax = 26.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 88
Tmin = 0.924, Tmax = 0.949k = 78
3013 measured reflectionsl = 148
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.036 w = 1/[σ2(Fo2) + (0.0486P)2 + 0.064P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.095(Δ/σ)max = 0.001
S = 1.05Δρmax = 0.18 e Å3
1996 reflectionsΔρmin = 0.20 e Å3
146 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.040 (6)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 804 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.35 (9)
Special details top

Experimental. IR (KBr, ν cm-1): 3340, 3160, 1605, 1540; 1H NMR (CDCl3): δ 9.20 (br, 1H), 7.45 (m, 5H), 7.40 (br, 1H), 5.22 (s, 1H), 3.75 (s, 4H); 13C NMR (CDCl3): δ 180.1, 165.0, 139.9, 133.4,127.4, 127.2, 72.8, 42.3.

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
Cl10.88618 (11)0.72632 (13)0.23600 (5)0.0698 (3)
N10.4995 (3)0.7641 (4)0.48199 (15)0.0451 (5)
N20.1841 (3)0.7930 (5)0.41534 (18)0.0632 (9)
O10.7841 (2)0.7512 (4)0.32938 (12)0.0565 (5)
C10.3939 (4)0.7716 (4)0.58667 (18)0.0459 (6)
H1A0.42860.88680.63080.055*
H1B0.42480.66020.63510.055*
C20.1707 (3)0.7729 (5)0.53831 (18)0.0505 (7)
H2A0.10300.65420.55600.061*
H2B0.09750.87960.56890.061*
C30.3755 (3)0.7778 (4)0.38634 (17)0.0359 (5)
C40.4355 (3)0.7787 (4)0.27344 (16)0.0370 (6)
H40.33580.78840.21170.044*
C50.6390 (3)0.7654 (4)0.25089 (16)0.0350 (5)
C60.6934 (3)0.7590 (4)0.12747 (17)0.0333 (5)
C70.5692 (4)0.8305 (4)0.0349 (2)0.0400 (6)
H70.44470.88620.04820.048*
C80.6264 (4)0.8209 (4)0.0773 (2)0.0463 (6)
H80.54150.86980.13870.056*
C90.8112 (3)0.7377 (5)0.09638 (17)0.0438 (6)
C100.9370 (4)0.6655 (4)0.0065 (2)0.0483 (7)
H101.06110.60950.02040.058*
C110.8788 (4)0.6762 (4)0.1048 (2)0.0430 (6)
H110.96490.62740.16570.052*
H10.611 (4)0.760 (6)0.476 (2)0.060 (9)*
H20.089 (4)0.791 (4)0.371 (2)0.053 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0832 (5)0.0871 (6)0.0437 (3)0.0124 (5)0.0323 (3)0.0115 (4)
N10.0342 (10)0.0697 (16)0.0312 (9)0.0019 (13)0.0021 (8)0.0005 (10)
N20.0276 (10)0.132 (3)0.0309 (10)0.0048 (14)0.0070 (8)0.0062 (13)
O10.0263 (7)0.1049 (17)0.0381 (8)0.0026 (12)0.0017 (6)0.0061 (11)
C10.0586 (14)0.0491 (17)0.0304 (10)0.0020 (14)0.0073 (9)0.0037 (11)
C20.0457 (13)0.072 (2)0.0363 (11)0.0018 (15)0.0145 (10)0.0013 (13)
C30.0303 (10)0.0442 (16)0.0334 (10)0.0003 (11)0.0029 (8)0.0001 (10)
C40.0271 (10)0.0566 (17)0.0270 (10)0.0012 (12)0.0016 (7)0.0001 (10)
C50.0343 (11)0.0369 (14)0.0343 (10)0.0005 (12)0.0060 (8)0.0003 (10)
C60.0312 (10)0.0350 (13)0.0346 (10)0.0009 (11)0.0088 (7)0.0011 (10)
C70.0376 (12)0.0429 (15)0.0406 (12)0.0062 (10)0.0099 (10)0.0014 (10)
C80.0538 (14)0.0493 (17)0.0366 (12)0.0002 (12)0.0087 (11)0.0055 (10)
C90.0558 (14)0.0430 (15)0.0355 (11)0.0065 (16)0.0207 (10)0.0044 (13)
C100.0408 (13)0.0530 (18)0.0542 (15)0.0044 (12)0.0215 (11)0.0022 (12)
C110.0378 (12)0.0471 (17)0.0453 (13)0.0066 (11)0.0106 (10)0.0056 (11)
Geometric parameters (Å, º) top
C3—C41.400 (3)C2—H2B0.9700
C4—C51.387 (3)C4—H40.9300
C3—N11.322 (3)C5—C61.506 (3)
C3—N21.333 (3)C6—C71.384 (3)
C5—O11.263 (2)C6—C111.393 (3)
Cl1—C91.7354 (19)C7—C81.387 (3)
N1—C11.451 (3)C7—H70.9300
N1—H10.74 (3)C8—C91.380 (4)
N2—C21.444 (3)C8—H80.9300
N2—H20.78 (3)C9—C101.368 (4)
C1—C21.523 (3)C10—C111.380 (3)
C1—H1A0.9700C10—H100.9300
C1—H1B0.9700C11—H110.9300
C2—H2A0.9700
C3—N1—C1113.33 (19)C3—C4—H4119.0
C3—N1—H1117 (2)O1—C5—C4123.23 (17)
C1—N1—H1129 (2)O1—C5—C6117.16 (16)
C3—N2—C2112.43 (19)C4—C5—C6119.56 (16)
C3—N2—H2123.6 (19)C7—C6—C11117.9 (2)
C2—N2—H2122.7 (19)C7—C6—C5123.69 (18)
N1—C1—C2101.90 (16)C11—C6—C5118.36 (18)
N1—C1—H1A111.4C6—C7—C8121.5 (2)
C2—C1—H1A111.4C6—C7—H7119.3
N1—C1—H1B111.4C8—C7—H7119.3
C2—C1—H1B111.4C9—C8—C7118.9 (2)
H1A—C1—H1B109.3C9—C8—H8120.5
N2—C2—C1103.01 (17)C7—C8—H8120.5
N2—C2—H2A111.2C10—C9—C8120.90 (19)
C1—C2—H2A111.2C10—C9—Cl1119.53 (18)
N2—C2—H2B111.2C8—C9—Cl1119.56 (19)
C1—C2—H2B111.2C9—C10—C11119.7 (2)
H2A—C2—H2B109.1C9—C10—H10120.2
N1—C3—N2108.61 (19)C11—C10—H10120.2
N1—C3—C4125.66 (19)C10—C11—C6121.1 (2)
N2—C3—C4125.72 (18)C10—C11—H11119.5
C5—C4—C3122.02 (17)C6—C11—H11119.5
C5—C4—H4119.0
C3—N1—C1—C25.5 (3)O1—C5—C6—C1121.1 (3)
C3—N2—C2—C18.3 (4)C4—C5—C6—C11156.3 (3)
N1—C1—C2—N27.7 (3)C11—C6—C7—C80.1 (4)
C1—N1—C3—N20.6 (3)C5—C6—C7—C8179.9 (2)
C1—N1—C3—C4178.6 (2)C6—C7—C8—C90.1 (4)
C2—N2—C3—N15.1 (4)C7—C8—C9—C100.1 (4)
C2—N2—C3—C4175.6 (3)C7—C8—C9—Cl1179.4 (2)
N1—C3—C4—C50.3 (4)C8—C9—C10—C110.1 (4)
N2—C3—C4—C5178.9 (3)Cl1—C9—C10—C11179.3 (2)
C3—C4—C5—O10.2 (4)C9—C10—C11—C60.2 (4)
C3—C4—C5—C6177.5 (2)C7—C6—C11—C100.1 (4)
O1—C5—C6—C7159.0 (3)C5—C6—C11—C10179.8 (2)
C4—C5—C6—C723.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.74 (3)2.12 (3)2.685 (3)133 (3)
N2—H2···O1i0.78 (3)2.04 (3)2.743 (3)152 (3)
Symmetry code: (i) x1, y, z.
 

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