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In the title compound, C
9H
10ClN
3·HC(O)NH
2, the benzene and imidazole rings make a dihedral angle of 43.3 (1)°. In the crystal structure, molecules are linked through weak intermolecular N—H
O, N—H
N and C—H
N hydrogen bonds, forming a three-dimensional framework.
Supporting information
CCDC reference: 647251
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.003 Å
- R factor = 0.042
- wR factor = 0.111
- Data-to-parameter ratio = 18.3
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT415_ALERT_2_B Short Inter D-H..H-X H4B .. H9B .. 2.00 Ang.
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3
PLAT420_ALERT_2_C D-H Without Acceptor N4 - H4B ... ?
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: COLLECT (Nonius, 1999); cell refinement: EVALCCD (Duisenberg et al., 2003); data reduction: SADABS (Sheldrick, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
N-(4-Chlorophenyl)-
N-(4,5-dihydro-1
H-imidazol-2-yl)amine
formamide solvate
top
Crystal data top
C9H10ClN3·CH3NO | F(000) = 504 |
Mr = 240.69 | Dx = 1.472 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2 y b c | Cell parameters from 204 reflections |
a = 8.5840 (5) Å | θ = 6–20° |
b = 13.2740 (4) Å | µ = 0.34 mm−1 |
c = 9.9080 (7) Å | T = 150 K |
β = 105.789 (5)° | Block, colourless |
V = 1086.4 (1) Å3 | 0.32 × 0.09 × 0.07 mm |
Z = 4 | |
Data collection top
Bruker–Nonius KappaCCD diffractometer | 2655 independent reflections |
Radiation source: fine-focus sealed tube | 2034 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
Detector resolution: 9 pixels mm-1 | θmax = 28.5°, θmin = 3.7° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | k = −17→15 |
Tmin = 0.900, Tmax = 0.977 | l = −13→13 |
15967 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0631P)2 + 0.4854P] where P = (Fo2 + 2Fc2)/3 |
2655 reflections | (Δ/σ)max < 0.001 |
145 parameters | Δρmax = 0.51 e Å−3 |
0 restraints | Δρmin = −0.57 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The observed criterion of F2 > σ(F2)
is used only for calculating -R-factor-obs 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 | x | y | z | Uiso*/Ueq | |
Cl1 | 0.03223 (5) | 0.13649 (3) | 1.04443 (5) | 0.0247 (1) | |
N1 | 0.57929 (19) | 0.26234 (11) | 0.82569 (16) | 0.0194 (4) | |
N2 | 0.78067 (19) | 0.23704 (11) | 0.71283 (16) | 0.0202 (4) | |
N3 | 0.64043 (18) | 0.10273 (12) | 0.74120 (16) | 0.0191 (4) | |
C1 | 0.4638 (2) | 0.14431 (13) | 0.96409 (18) | 0.0191 (5) | |
C2 | 0.3325 (2) | 0.11613 (14) | 1.01374 (19) | 0.0207 (5) | |
C3 | 0.1971 (2) | 0.17666 (14) | 0.98729 (17) | 0.0183 (5) | |
C4 | 0.1892 (2) | 0.26713 (14) | 0.91624 (19) | 0.0202 (5) | |
C5 | 0.3184 (2) | 0.29344 (14) | 0.86291 (19) | 0.0203 (5) | |
C6 | 0.4535 (2) | 0.23145 (13) | 0.88365 (18) | 0.0167 (5) | |
C7 | 0.6622 (2) | 0.20147 (13) | 0.76214 (17) | 0.0161 (4) | |
C8 | 0.8552 (2) | 0.15664 (14) | 0.6514 (2) | 0.0210 (5) | |
C9 | 0.7509 (2) | 0.06467 (14) | 0.6622 (2) | 0.0234 (5) | |
O1 | 0.61744 (16) | 0.46791 (9) | 0.79428 (14) | 0.0220 (4) | |
N4 | 0.87429 (17) | 0.43528 (11) | 0.79633 (17) | 0.0201 (4) | |
C10 | 0.7618 (2) | 0.49239 (13) | 0.80339 (18) | 0.0194 (5) | |
H1 | 0.55720 | 0.10520 | 0.98460 | 0.0230* | |
H1A | 0.60460 | 0.32520 | 0.83170 | 0.0230* | |
H2 | 0.33650 | 0.05680 | 1.06440 | 0.0250* | |
H3 | 0.57220 | 0.06670 | 0.76950 | 0.0230* | |
H4 | 0.10010 | 0.30940 | 0.90430 | 0.0240* | |
H5 | 0.31400 | 0.35310 | 0.81290 | 0.0240* | |
H8A | 0.96710 | 0.14630 | 0.70400 | 0.0250* | |
H8B | 0.85070 | 0.17130 | 0.55450 | 0.0250* | |
H9A | 0.69110 | 0.04120 | 0.56990 | 0.0280* | |
H9B | 0.81710 | 0.01000 | 0.71200 | 0.0280* | |
H4A | 0.85710 | 0.37170 | 0.78400 | 0.0240* | |
H4B | 0.96920 | 0.45940 | 0.80380 | 0.0240* | |
H10 | 0.78690 | 0.56050 | 0.81680 | 0.0230* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0240 (2) | 0.0244 (2) | 0.0301 (2) | −0.0013 (2) | 0.0149 (2) | 0.0001 (2) |
N1 | 0.0196 (7) | 0.0125 (7) | 0.0277 (8) | 0.0005 (6) | 0.0093 (6) | 0.0009 (6) |
N2 | 0.0183 (7) | 0.0163 (7) | 0.0286 (8) | −0.0007 (6) | 0.0109 (6) | 0.0001 (6) |
N3 | 0.0184 (7) | 0.0166 (7) | 0.0255 (8) | −0.0009 (6) | 0.0115 (6) | −0.0008 (6) |
C1 | 0.0218 (8) | 0.0151 (8) | 0.0211 (8) | 0.0061 (7) | 0.0071 (7) | 0.0013 (7) |
C2 | 0.0289 (9) | 0.0164 (8) | 0.0200 (8) | 0.0049 (7) | 0.0119 (7) | 0.0033 (6) |
C3 | 0.0196 (8) | 0.0196 (8) | 0.0170 (8) | −0.0016 (7) | 0.0071 (7) | −0.0025 (7) |
C4 | 0.0166 (8) | 0.0186 (8) | 0.0254 (9) | 0.0052 (7) | 0.0055 (7) | 0.0030 (7) |
C5 | 0.0206 (9) | 0.0170 (8) | 0.0241 (9) | 0.0030 (7) | 0.0073 (7) | 0.0041 (7) |
C6 | 0.0175 (8) | 0.0146 (8) | 0.0177 (8) | −0.0002 (6) | 0.0044 (6) | −0.0013 (6) |
C7 | 0.0147 (7) | 0.0150 (8) | 0.0172 (8) | 0.0000 (6) | 0.0019 (6) | 0.0025 (6) |
C8 | 0.0192 (8) | 0.0199 (9) | 0.0264 (9) | −0.0010 (7) | 0.0105 (7) | −0.0019 (7) |
C9 | 0.0275 (9) | 0.0170 (8) | 0.0308 (9) | −0.0021 (7) | 0.0164 (8) | −0.0033 (7) |
O1 | 0.0185 (6) | 0.0155 (6) | 0.0334 (7) | 0.0011 (5) | 0.0094 (5) | 0.0015 (5) |
N4 | 0.0112 (7) | 0.0126 (7) | 0.0392 (9) | −0.0012 (5) | 0.0117 (6) | −0.0035 (6) |
C10 | 0.0204 (8) | 0.0139 (8) | 0.0251 (8) | −0.0009 (7) | 0.0081 (7) | 0.0006 (7) |
Geometric parameters (Å, º) top
Cl1—C3 | 1.7446 (18) | C2—C3 | 1.378 (3) |
O1—C10 | 1.260 (2) | C3—C4 | 1.384 (3) |
N1—C6 | 1.415 (2) | C4—C5 | 1.397 (3) |
N1—C7 | 1.342 (2) | C5—C6 | 1.391 (3) |
N2—C8 | 1.460 (2) | C8—C9 | 1.535 (3) |
N2—C7 | 1.329 (2) | C1—H1 | 0.9300 |
N3—C7 | 1.332 (2) | C2—H2 | 0.9300 |
N3—C9 | 1.473 (2) | C4—H4 | 0.9300 |
N1—H1A | 0.8600 | C5—H5 | 0.9300 |
N3—H3 | 0.8600 | C8—H8B | 0.9700 |
N4—C10 | 1.245 (2) | C8—H8A | 0.9700 |
N4—H4A | 0.8600 | C9—H9A | 0.9700 |
N4—H4B | 0.8600 | C9—H9B | 0.9700 |
C1—C2 | 1.398 (3) | C10—H10 | 0.9300 |
C1—C6 | 1.394 (2) | | |
| | | |
Cl1···C5i | 3.5550 (19) | C10···H1A | 2.6500 |
Cl1···N2ii | 3.4966 (17) | H1···N3 | 2.7000 |
Cl1···N4ii | 3.2888 (17) | H1···C7 | 2.9000 |
Cl1···C8ii | 3.4423 (19) | H1···H2iii | 2.4400 |
Cl1···H9Biii | 3.1000 | H1···H3 | 2.2300 |
Cl1···H4Aii | 3.1400 | H1···C2iii | 3.0900 |
Cl1···H4Bii | 3.0500 | H1A···O1 | 1.9400 |
Cl1···H5i | 3.0700 | H1A···N4 | 2.8400 |
Cl1···H8Bii | 3.0100 | H1A···C10 | 2.6500 |
O1···N3iv | 2.793 (2) | H1A···H4A | 2.4200 |
O1···C1iv | 3.399 (2) | H1A···H5 | 2.4800 |
O1···N1 | 2.7759 (19) | H2···H3iii | 2.3000 |
O1···C2v | 3.355 (2) | H2···O1i | 2.8500 |
O1···H2v | 2.8500 | H2···H1iii | 2.4400 |
O1···H3iv | 2.0500 | H2···N3iii | 2.8300 |
O1···H1A | 1.9400 | H3···H1 | 2.2300 |
O1···H9Ai | 2.6300 | H3···C1 | 2.5700 |
N1···O1 | 2.7759 (19) | H3···C6 | 2.7800 |
N2···Cl1vi | 3.4966 (17) | H3···H2iii | 2.3000 |
N2···N4 | 2.809 (2) | H3···O1vii | 2.0500 |
N3···O1vii | 2.793 (2) | H3···C10vii | 2.9300 |
N3···C1 | 3.050 (2) | H4···N4x | 2.5600 |
N4···N2 | 2.809 (2) | H4···H4Ax | 2.2600 |
N4···Cl1vi | 3.2888 (17) | H4···H4Bx | 2.3700 |
N1···H8Bi | 2.9100 | H4A···H4ix | 2.2600 |
N1···H4A | 2.9200 | H4A···N1 | 2.9200 |
N2···H4A | 1.9700 | H4A···N2 | 1.9700 |
N3···H2iii | 2.8300 | H4A···C7 | 2.7800 |
N3···H1 | 2.7000 | H4A···H1A | 2.4200 |
N4···H1A | 2.8400 | H4A···Cl1vi | 3.1400 |
N4···H9Bviii | 2.8500 | H4B···Cl1vi | 3.0500 |
N4···H4ix | 2.5600 | H4B···H4ix | 2.3700 |
C1···N3 | 3.050 (2) | H4B···C8viii | 2.9900 |
C1···C10vii | 3.471 (2) | H4B···C9viii | 2.7200 |
C1···O1vii | 3.399 (2) | H4B···H8Aviii | 2.5500 |
C2···O1i | 3.355 (2) | H4B···H9Bviii | 2.0000 |
C2···C10vii | 3.441 (3) | H5···H1A | 2.4800 |
C5···Cl1v | 3.5550 (19) | H5···Cl1v | 3.0700 |
C8···Cl1vi | 3.4423 (19) | H5···C9iv | 2.8900 |
C10···C2iv | 3.441 (3) | H5···H9Biv | 2.3500 |
C10···C1iv | 3.471 (2) | H5···C2v | 3.0400 |
C1···H3 | 2.5700 | H8A···H4Bxi | 2.5500 |
C2···H1iii | 3.0900 | H8A···C3ix | 2.9900 |
C2···H5i | 3.0400 | H8A···C4ix | 2.9100 |
C3···H8Ax | 2.9900 | H8A···H10xi | 2.4600 |
C4···H8Ax | 2.9100 | H8B···N1v | 2.9100 |
C6···H3 | 2.7800 | H8B···Cl1vi | 3.0100 |
C7···H4A | 2.7800 | H9A···O1v | 2.6300 |
C7···H1 | 2.9000 | H9A···C10v | 2.9000 |
C8···H4Bxi | 2.9900 | H9B···Cl1iii | 3.1000 |
C9···H5vii | 2.8900 | H9B···N4xi | 2.8500 |
C9···H4Bxi | 2.7200 | H9B···H4Bxi | 2.0000 |
C10···H3iv | 2.9300 | H9B···H5vii | 2.3500 |
C10···H9Ai | 2.9000 | H10···H8Aviii | 2.4600 |
| | | |
C6—N1—C7 | 125.24 (15) | N2—C8—C9 | 102.85 (14) |
C7—N2—C8 | 111.07 (14) | N3—C9—C8 | 103.67 (15) |
C7—N3—C9 | 109.68 (15) | C2—C1—H1 | 120.00 |
C6—N1—H1A | 117.00 | C6—C1—H1 | 120.00 |
C7—N1—H1A | 117.00 | C1—C2—H2 | 120.00 |
C7—N3—H3 | 125.00 | C3—C2—H2 | 120.00 |
C9—N3—H3 | 125.00 | C5—C4—H4 | 121.00 |
C10—N4—H4A | 120.00 | C3—C4—H4 | 121.00 |
C10—N4—H4B | 120.00 | C4—C5—H5 | 120.00 |
H4A—N4—H4B | 120.00 | C6—C5—H5 | 120.00 |
C2—C1—C6 | 119.44 (16) | N2—C8—H8A | 111.00 |
C1—C2—C3 | 119.74 (17) | N2—C8—H8B | 111.00 |
Cl1—C3—C4 | 119.89 (14) | C9—C8—H8A | 111.00 |
C2—C3—C4 | 121.64 (17) | C9—C8—H8B | 111.00 |
Cl1—C3—C2 | 118.47 (14) | H8A—C8—H8B | 109.00 |
C3—C4—C5 | 118.38 (17) | C8—C9—H9A | 111.00 |
C4—C5—C6 | 120.81 (17) | H9A—C9—H9B | 109.00 |
C1—C6—C5 | 119.74 (16) | N3—C9—H9B | 111.00 |
N1—C6—C5 | 117.80 (15) | C8—C9—H9B | 111.00 |
N1—C6—C1 | 122.41 (16) | N3—C9—H9A | 111.00 |
N1—C7—N2 | 121.02 (16) | O1—C10—N4 | 126.99 (17) |
N2—C7—N3 | 112.41 (16) | O1—C10—H10 | 116.00 |
N1—C7—N3 | 126.57 (16) | N4—C10—H10 | 117.00 |
| | | |
C7—N1—C6—C1 | 43.5 (3) | C2—C1—C6—C5 | 5.0 (3) |
C7—N1—C6—C5 | −139.01 (18) | C2—C1—C6—N1 | −177.58 (16) |
C6—N1—C7—N2 | −178.83 (16) | C1—C2—C3—C4 | −2.2 (3) |
C6—N1—C7—N3 | 0.7 (3) | C1—C2—C3—Cl1 | 177.33 (14) |
C8—N2—C7—N1 | 178.67 (16) | C2—C3—C4—C5 | 4.2 (3) |
C8—N2—C7—N3 | −0.9 (2) | Cl1—C3—C4—C5 | −175.32 (14) |
C7—N2—C8—C9 | 4.11 (19) | C3—C4—C5—C6 | −1.6 (3) |
C9—N3—C7—N2 | −3.0 (2) | C4—C5—C6—C1 | −3.0 (3) |
C7—N3—C9—C8 | 5.26 (19) | C4—C5—C6—N1 | 179.47 (16) |
C9—N3—C7—N1 | 177.49 (17) | N2—C8—C9—N3 | −5.40 (18) |
C6—C1—C2—C3 | −2.5 (3) | | |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x−1, −y+1/2, z+1/2; (iii) −x+1, −y, −z+2; (iv) −x+1, y+1/2, −z+3/2; (v) x, −y+1/2, z−1/2; (vi) x+1, −y+1/2, z−1/2; (vii) −x+1, y−1/2, −z+3/2; (viii) −x+2, y+1/2, −z+3/2; (ix) x+1, y, z; (x) x−1, y, z; (xi) −x+2, y−1/2, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1 | 0.86 | 1.94 | 2.7759 (19) | 164 |
N3—H3···O1vii | 0.86 | 2.05 | 2.793 (2) | 144 |
N4—H4A···N2 | 0.86 | 1.97 | 2.809 (2) | 166 |
C4—H4···N4x | 0.93 | 2.56 | 3.457 (2) | 162 |
Symmetry codes: (vii) −x+1, y−1/2, −z+3/2; (x) x−1, y, z. |
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