In the title compound, C
17H
19ClN
2O
3, the dihedral angles formed by the butyl group and the imidazole ring with the benzene ring are 86.4 (4) and 88.9 (3)°, respectively. The dihedral angle between the imidazole ring and the butyl group is 77.1 (5)°. The structure is stabilized by C—H
O and C—H
π interactions.
Supporting information
CCDC reference: 259558
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.059
- wR factor = 0.178
- Data-to-parameter ratio = 14.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.13 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.45 Ratio
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C16
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C1 - C2 ... 1.38 Ang.
PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C3 - C4 ... 1.42 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 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
4 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
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989; program(s) used to solve structure: SHELXTL/PC (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC; software used to prepare material for publication: WinGX (Farrugia, 1999).
Methyl 4-[(2-butyl-4-chloro-5-formyl-1
H-imidazol-1-yl)methyl]benzoate
top
Crystal data top
C17H19ClN2O3 | F(000) = 704 |
Mr = 334.79 | Dx = 1.274 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -p 2yn | Cell parameters from 25 reflections |
a = 11.946 (2) Å | θ = 4–14° |
b = 9.7085 (19) Å | µ = 0.23 mm−1 |
c = 15.247 (3) Å | T = 293 K |
β = 99.26 (3)° | Prism, colorless |
V = 1745.2 (6) Å3 | 0.30 × 0.30 × 0.20 mm |
Z = 4 | |
Data collection top
Enraf-Nonius CAD-4 diffractometer | Rint = 0.036 |
Radiation source: fine-focus sealed tube | θmax = 25.1°, θmin = 2.0° |
Graphite monochromator | h = −14→0 |
ω scans | k = −11→0 |
3226 measured reflections | l = −17→18 |
3070 independent reflections | 3 standard reflections every 100 reflections |
1705 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.059 | H-atom parameters constrained |
wR(F2) = 0.178 | w = 1/[σ2(Fo2) + (0.0459P)2 + 1.4956P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
3070 reflections | Δρmax = 0.29 e Å−3 |
209 parameters | Δρmin = −0.21 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0047 (14) |
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 | x | y | z | Uiso*/Ueq | |
Cl1 | 0.47494 (11) | 0.14162 (12) | 0.59477 (7) | 0.1022 (5) | |
O1 | 0.1915 (3) | 0.0439 (4) | 0.3706 (2) | 0.1134 (11) | |
O2 | 0.3367 (4) | −0.1800 (4) | −0.0474 (2) | 0.1437 (15) | |
O3 | 0.5031 (4) | −0.2043 (3) | 0.0403 (2) | 0.1085 (10) | |
N1 | 0.5073 (3) | 0.3125 (4) | 0.4655 (2) | 0.0857 (10) | |
N2 | 0.3664 (3) | 0.2608 (3) | 0.35546 (19) | 0.0707 (8) | |
C1 | 0.7336 (7) | 0.5211 (11) | 0.2032 (5) | 0.214 (4) | |
H1B | 0.7546 | 0.6010 | 0.1725 | 0.321* | |
H1C | 0.7166 | 0.4466 | 0.1617 | 0.321* | |
H1D | 0.7953 | 0.4950 | 0.2486 | 0.321* | |
C2 | 0.6394 (6) | 0.5505 (8) | 0.2414 (4) | 0.158 (3) | |
H2A | 0.5780 | 0.5786 | 0.1953 | 0.189* | |
H2B | 0.6566 | 0.6272 | 0.2821 | 0.189* | |
C3 | 0.5988 (5) | 0.4245 (6) | 0.2934 (4) | 0.131 (2) | |
H3A | 0.5850 | 0.3464 | 0.2535 | 0.157* | |
H3B | 0.6588 | 0.3992 | 0.3414 | 0.157* | |
C4 | 0.4986 (4) | 0.4535 (5) | 0.3291 (3) | 0.1140 (16) | |
H4A | 0.4387 | 0.4760 | 0.2803 | 0.137* | |
H4B | 0.5121 | 0.5347 | 0.3664 | 0.137* | |
C5 | 0.4573 (4) | 0.3413 (4) | 0.3822 (3) | 0.0820 (11) | |
C6 | 0.4437 (3) | 0.2119 (4) | 0.4904 (2) | 0.0732 (10) | |
C7 | 0.3548 (3) | 0.1745 (4) | 0.4261 (2) | 0.0686 (10) | |
C8 | 0.2686 (4) | 0.0731 (4) | 0.4286 (3) | 0.0873 (12) | |
H8A | 0.2725 | 0.0240 | 0.4814 | 0.105* | |
C9 | 0.2941 (3) | 0.2599 (4) | 0.2676 (2) | 0.0823 (12) | |
H9A | 0.2995 | 0.3490 | 0.2397 | 0.099* | |
H9B | 0.2159 | 0.2469 | 0.2755 | 0.099* | |
C10 | 0.3250 (3) | 0.1501 (4) | 0.2067 (2) | 0.0685 (10) | |
C11 | 0.2511 (3) | 0.1251 (5) | 0.1278 (3) | 0.0839 (12) | |
H11A | 0.1837 | 0.1745 | 0.1152 | 0.101* | |
C12 | 0.2765 (4) | 0.0288 (5) | 0.0689 (3) | 0.0907 (13) | |
H12A | 0.2260 | 0.0133 | 0.0167 | 0.109* | |
C13 | 0.3759 (4) | −0.0459 (4) | 0.0852 (2) | 0.0793 (11) | |
C14 | 0.4509 (3) | −0.0219 (4) | 0.1635 (2) | 0.0788 (11) | |
H14A | 0.5184 | −0.0710 | 0.1756 | 0.095* | |
C15 | 0.4243 (3) | 0.0755 (4) | 0.2230 (2) | 0.0773 (11) | |
H15A | 0.4745 | 0.0910 | 0.2753 | 0.093* | |
C16 | 0.4002 (5) | −0.1493 (5) | 0.0186 (3) | 0.0947 (13) | |
C17 | 0.5356 (6) | −0.3073 (5) | −0.0202 (4) | 0.143 (2) | |
H17A | 0.6109 | −0.3396 | 0.0018 | 0.214* | |
H17B | 0.5340 | −0.2671 | −0.0780 | 0.214* | |
H17C | 0.4835 | −0.3832 | −0.0245 | 0.214* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.1386 (11) | 0.0974 (8) | 0.0639 (6) | −0.0001 (7) | −0.0046 (6) | 0.0080 (6) |
O1 | 0.109 (2) | 0.124 (3) | 0.102 (2) | −0.029 (2) | 0.0004 (19) | −0.016 (2) |
O2 | 0.161 (3) | 0.172 (4) | 0.096 (2) | −0.038 (3) | 0.015 (2) | −0.051 (3) |
O3 | 0.157 (3) | 0.085 (2) | 0.092 (2) | 0.000 (2) | 0.043 (2) | −0.0120 (17) |
N1 | 0.095 (2) | 0.077 (2) | 0.077 (2) | −0.009 (2) | −0.0086 (18) | 0.0058 (18) |
N2 | 0.080 (2) | 0.0671 (19) | 0.0614 (17) | 0.0053 (17) | 0.0019 (15) | −0.0002 (16) |
C1 | 0.171 (7) | 0.291 (11) | 0.190 (8) | −0.034 (8) | 0.057 (6) | 0.027 (8) |
C2 | 0.148 (5) | 0.199 (7) | 0.140 (5) | −0.024 (5) | 0.063 (4) | 0.013 (5) |
C3 | 0.133 (5) | 0.155 (5) | 0.111 (4) | 0.007 (4) | 0.044 (4) | 0.034 (4) |
C4 | 0.113 (4) | 0.111 (4) | 0.115 (4) | −0.008 (3) | 0.009 (3) | 0.032 (3) |
C5 | 0.092 (3) | 0.075 (3) | 0.077 (3) | −0.002 (2) | 0.004 (2) | 0.010 (2) |
C6 | 0.091 (3) | 0.066 (2) | 0.060 (2) | 0.006 (2) | 0.003 (2) | −0.0031 (19) |
C7 | 0.080 (2) | 0.062 (2) | 0.063 (2) | 0.004 (2) | 0.0081 (18) | −0.0057 (18) |
C8 | 0.102 (3) | 0.083 (3) | 0.076 (3) | −0.009 (3) | 0.011 (2) | −0.008 (2) |
C9 | 0.084 (3) | 0.088 (3) | 0.069 (2) | 0.016 (2) | −0.005 (2) | 0.005 (2) |
C10 | 0.072 (2) | 0.077 (2) | 0.0533 (19) | 0.000 (2) | 0.0015 (17) | 0.0098 (18) |
C11 | 0.077 (3) | 0.106 (3) | 0.065 (2) | 0.001 (2) | −0.0022 (19) | 0.005 (2) |
C12 | 0.085 (3) | 0.119 (4) | 0.062 (2) | −0.019 (3) | −0.005 (2) | 0.000 (3) |
C13 | 0.100 (3) | 0.080 (3) | 0.060 (2) | −0.024 (2) | 0.020 (2) | −0.005 (2) |
C14 | 0.086 (3) | 0.081 (3) | 0.068 (2) | 0.003 (2) | 0.006 (2) | 0.004 (2) |
C15 | 0.086 (3) | 0.085 (3) | 0.054 (2) | 0.007 (2) | −0.0068 (18) | 0.000 (2) |
C16 | 0.114 (4) | 0.094 (3) | 0.080 (3) | −0.023 (3) | 0.028 (3) | −0.002 (3) |
C17 | 0.235 (7) | 0.087 (3) | 0.124 (4) | −0.001 (4) | 0.081 (4) | −0.017 (3) |
Geometric parameters (Å, º) top
Cl1—C6 | 1.717 (4) | C4—H4B | 0.970 |
O1—C8 | 1.204 (5) | C6—C7 | 1.373 (5) |
O2—C16 | 1.196 (5) | C7—C8 | 1.429 (5) |
O3—C16 | 1.332 (6) | C8—H8A | 0.930 |
O3—C17 | 1.455 (5) | C9—C10 | 1.498 (5) |
N1—C6 | 1.329 (5) | C9—H9A | 0.970 |
N1—C5 | 1.343 (5) | C9—H9B | 0.970 |
N2—C5 | 1.347 (5) | C10—C15 | 1.378 (5) |
N2—C7 | 1.389 (4) | C10—C11 | 1.395 (5) |
N2—C9 | 1.473 (4) | C11—C12 | 1.364 (6) |
C1—C2 | 1.379 (8) | C11—H11A | 0.930 |
C1—H1B | 0.960 | C12—C13 | 1.379 (6) |
C1—H1C | 0.960 | C12—H12A | 0.930 |
C1—H1D | 0.960 | C13—C14 | 1.392 (5) |
C2—C3 | 1.575 (8) | C13—C16 | 1.489 (6) |
C2—H2A | 0.970 | C14—C15 | 1.383 (5) |
C2—H2B | 0.970 | C14—H14A | 0.930 |
C3—C4 | 1.421 (6) | C15—H15A | 0.930 |
C3—H3A | 0.970 | C17—H17A | 0.960 |
C3—H3B | 0.970 | C17—H17B | 0.960 |
C4—C5 | 1.488 (6) | C17—H17C | 0.960 |
C4—H4A | 0.970 | | |
| | | |
C16—O3—C17 | 116.6 (4) | N2—C7—C8 | 126.7 (3) |
C6—N1—C5 | 103.6 (3) | O1—C8—C7 | 127.7 (4) |
C5—N2—C7 | 106.9 (3) | O1—C8—H8A | 116.1 |
C5—N2—C9 | 127.3 (3) | C7—C8—H8A | 116.1 |
C7—N2—C9 | 125.8 (3) | N2—C9—C10 | 113.7 (3) |
C2—C1—H1B | 109.5 | N2—C9—H9A | 108.8 |
C2—C1—H1C | 109.5 | C10—C9—H9A | 108.8 |
H1B—C1—H1C | 109.5 | N2—C9—H9B | 108.8 |
C2—C1—H1D | 109.5 | C10—C9—H9B | 108.8 |
H1B—C1—H1D | 109.5 | H9A—C9—H9B | 107.7 |
H1C—C1—H1D | 109.5 | C15—C10—C11 | 118.1 (4) |
C1—C2—C3 | 113.0 (7) | C15—C10—C9 | 123.6 (3) |
C1—C2—H2A | 109.0 | C11—C10—C9 | 118.3 (3) |
C3—C2—H2A | 109.0 | C12—C11—C10 | 120.7 (4) |
C1—C2—H2B | 109.0 | C12—C11—H11A | 119.7 |
C3—C2—H2B | 109.0 | C10—C11—H11A | 119.7 |
H2A—C2—H2B | 107.8 | C11—C12—C13 | 121.2 (4) |
C4—C3—C2 | 112.7 (5) | C11—C12—H12A | 119.4 |
C4—C3—H3A | 109.1 | C13—C12—H12A | 119.4 |
C2—C3—H3A | 109.1 | C12—C13—C14 | 118.9 (4) |
C4—C3—H3B | 109.1 | C12—C13—C16 | 119.2 (4) |
C2—C3—H3B | 109.1 | C14—C13—C16 | 121.9 (5) |
H3A—C3—H3B | 107.8 | C15—C14—C13 | 119.6 (4) |
C3—C4—C5 | 115.9 (5) | C15—C14—H14A | 120.2 |
C3—C4—H4A | 108.3 | C13—C14—H14A | 120.2 |
C5—C4—H4A | 108.3 | C10—C15—C14 | 121.5 (3) |
C3—C4—H4B | 108.3 | C10—C15—H15A | 119.2 |
C5—C4—H4B | 108.3 | C14—C15—H15A | 119.2 |
H4A—C4—H4B | 107.4 | O2—C16—O3 | 122.9 (5) |
N1—C5—N2 | 112.3 (3) | O2—C16—C13 | 125.1 (5) |
N1—C5—C4 | 122.1 (4) | O3—C16—C13 | 112.0 (4) |
N2—C5—C4 | 125.5 (4) | O3—C17—H17A | 109.5 |
N1—C6—C7 | 113.8 (3) | O3—C17—H17B | 109.5 |
N1—C6—Cl1 | 120.5 (3) | H17A—C17—H17B | 109.5 |
C7—C6—Cl1 | 125.7 (3) | O3—C17—H17C | 109.5 |
C6—C7—N2 | 103.4 (3) | H17A—C17—H17C | 109.5 |
C6—C7—C8 | 129.9 (4) | H17B—C17—H17C | 109.5 |
| | | |
C1—C2—C3—C4 | −177.2 (6) | N2—C7—C8—O1 | 0.5 (7) |
C2—C3—C4—C5 | −177.7 (5) | C5—N2—C9—C10 | 97.1 (5) |
C6—N1—C5—N2 | −0.6 (5) | C7—N2—C9—C10 | −80.8 (5) |
C6—N1—C5—C4 | 177.6 (4) | N2—C9—C10—C15 | −12.7 (6) |
C7—N2—C5—N1 | 0.8 (5) | N2—C9—C10—C11 | 169.5 (3) |
C9—N2—C5—N1 | −177.5 (3) | C15—C10—C11—C12 | 0.3 (6) |
C7—N2—C5—C4 | −177.4 (4) | C9—C10—C11—C12 | 178.2 (4) |
C9—N2—C5—C4 | 4.4 (7) | C10—C11—C12—C13 | −0.3 (6) |
C3—C4—C5—N1 | 75.9 (6) | C11—C12—C13—C14 | 0.1 (6) |
C3—C4—C5—N2 | −106.1 (6) | C11—C12—C13—C16 | −179.7 (4) |
C5—N1—C6—C7 | 0.2 (5) | C12—C13—C14—C15 | 0.2 (6) |
C5—N1—C6—Cl1 | −179.3 (3) | C16—C13—C14—C15 | 179.9 (4) |
N1—C6—C7—N2 | 0.2 (4) | C11—C10—C15—C14 | −0.1 (6) |
Cl1—C6—C7—N2 | 179.7 (3) | C9—C10—C15—C14 | −177.8 (4) |
N1—C6—C7—C8 | −179.1 (4) | C13—C14—C15—C10 | −0.2 (6) |
Cl1—C6—C7—C8 | 0.4 (6) | C17—O3—C16—O2 | −1.0 (7) |
C5—N2—C7—C6 | −0.6 (4) | C17—O3—C16—C13 | 179.8 (3) |
C9—N2—C7—C6 | 177.7 (3) | C12—C13—C16—O2 | −4.5 (7) |
C5—N2—C7—C8 | 178.8 (4) | C14—C13—C16—O2 | 175.7 (5) |
C9—N2—C7—C8 | −3.0 (6) | C12—C13—C16—O3 | 174.7 (4) |
C6—C7—C8—O1 | 179.6 (4) | C14—C13—C16—O3 | −5.1 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9A···O1i | 0.97 | 2.55 | 3.491 (5) | 165 |
C9—H9B···O1 | 0.97 | 2.49 | 2.998 (5) | 112 |
Symmetry code: (i) −x+1/2, y+1/2, −z+1/2. |