The title compound, C
22H
20ClN
3O, (I), is used as an intermediate for the synthesis of the antihypertensive drug losartan. Bond lengths and angles are unexceptional. The crystal packing is stabilized by one C—H
O and one C—H
N contact. It is noteworthy that (I) is isomorphous with a closely related compound which differs in having a but-2-enyl chain instead of a butyl chain on the imidazole ring.
Supporting information
CCDC reference: 270319
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.002 Å
- R factor = 0.042
- wR factor = 0.112
- Data-to-parameter ratio = 18.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.59 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for C22 - C27 .. 5.49 su
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C22 - C27 ... 1.44 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 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
3 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
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON and SHELXL97.
4'-(2-Butyl-4-chloro-5-formylimidazol-1-ylmethyl)biphenyl-2-carbonitrile
top
Crystal data top
C22H20ClN3O | F(000) = 792 |
Mr = 377.86 | Dx = 1.298 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 35462 reflections |
a = 8.9729 (4) Å | θ = 2.4–27.9° |
b = 22.6232 (9) Å | µ = 0.21 mm−1 |
c = 9.9288 (5) Å | T = 173 K |
β = 106.427 (4)° | Block, colourless |
V = 1933.23 (15) Å3 | 0.32 × 0.25 × 0.22 mm |
Z = 4 | |
Data collection top
Stoe IPDS-II two-circle diffractometer | 4448 independent reflections |
Radiation source: fine-focus sealed tube | 4037 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
ω scans | θmax = 27.7°, θmin = 2.3° |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −11→11 |
Tmin = 0.923, Tmax = 0.955 | k = −29→29 |
31411 measured reflections | l = −12→12 |
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) = 0.112 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.053P)2 + 0.8177P] where P = (Fo2 + 2Fc2)/3 |
4448 reflections | (Δ/σ)max = 0.001 |
244 parameters | Δρmax = 0.51 e Å−3 |
0 restraints | Δρmin = −0.42 e Å−3 |
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 | 0.30260 (5) | 0.815687 (19) | 0.28852 (5) | 0.05432 (15) | |
C1 | 0.56545 (15) | 0.61083 (5) | 0.46761 (14) | 0.0266 (3) | |
H1A | 0.6788 | 0.6077 | 0.5122 | 0.032* | |
H1B | 0.5425 | 0.5929 | 0.3730 | 0.032* | |
N1 | 0.52046 (12) | 0.67400 (5) | 0.45370 (12) | 0.0253 (2) | |
C2 | 0.41095 (15) | 0.70051 (6) | 0.34126 (15) | 0.0303 (3) | |
C3 | 0.41141 (16) | 0.75900 (6) | 0.38232 (16) | 0.0338 (3) | |
N4 | 0.51175 (14) | 0.76936 (5) | 0.50970 (13) | 0.0328 (3) | |
C5 | 0.57655 (15) | 0.71658 (6) | 0.55069 (14) | 0.0272 (3) | |
C6 | 0.69707 (17) | 0.70626 (6) | 0.68690 (15) | 0.0328 (3) | |
H6A | 0.7712 | 0.6759 | 0.6735 | 0.039* | |
H6B | 0.6465 | 0.6909 | 0.7564 | 0.039* | |
C7 | 0.78594 (17) | 0.76271 (6) | 0.74404 (16) | 0.0351 (3) | |
H7A | 0.8287 | 0.7796 | 0.6708 | 0.042* | |
H7B | 0.7121 | 0.7918 | 0.7631 | 0.042* | |
C8 | 0.9166 (2) | 0.75399 (8) | 0.87568 (18) | 0.0488 (4) | |
H8A | 0.9891 | 0.7238 | 0.8585 | 0.059* | |
H8B | 0.8741 | 0.7391 | 0.9510 | 0.059* | |
C9 | 1.0054 (3) | 0.81133 (9) | 0.9240 (2) | 0.0595 (5) | |
H9A | 1.0892 | 0.8040 | 1.0101 | 0.089* | |
H9B | 0.9343 | 0.8411 | 0.9425 | 0.089* | |
H9C | 1.0496 | 0.8257 | 0.8504 | 0.089* | |
C10 | 0.32151 (17) | 0.67307 (7) | 0.21157 (16) | 0.0363 (3) | |
H10 | 0.2551 | 0.6982 | 0.1439 | 0.044* | |
O10 | 0.32308 (14) | 0.62101 (5) | 0.18080 (12) | 0.0441 (3) | |
C11 | 0.48048 (14) | 0.57667 (5) | 0.55444 (13) | 0.0234 (2) | |
C12 | 0.55815 (14) | 0.55719 (6) | 0.68901 (14) | 0.0271 (3) | |
H12 | 0.6654 | 0.5659 | 0.7273 | 0.033* | |
C13 | 0.48063 (15) | 0.52510 (6) | 0.76797 (13) | 0.0267 (3) | |
H13 | 0.5355 | 0.5120 | 0.8595 | 0.032* | |
C14 | 0.32270 (14) | 0.51194 (5) | 0.71406 (13) | 0.0229 (2) | |
C15 | 0.24575 (14) | 0.53124 (6) | 0.57833 (13) | 0.0264 (3) | |
H15 | 0.1387 | 0.5223 | 0.5395 | 0.032* | |
C16 | 0.32321 (15) | 0.56319 (6) | 0.49953 (13) | 0.0267 (3) | |
H16 | 0.2688 | 0.5760 | 0.4076 | 0.032* | |
C21 | 0.24103 (14) | 0.47628 (5) | 0.79727 (13) | 0.0238 (2) | |
C22 | 0.08868 (15) | 0.48978 (6) | 0.80110 (14) | 0.0266 (3) | |
C23 | 0.00994 (17) | 0.45370 (6) | 0.87355 (15) | 0.0328 (3) | |
H23 | −0.0940 | 0.4626 | 0.8719 | 0.039* | |
C24 | 0.0842 (2) | 0.40516 (6) | 0.94735 (16) | 0.0369 (3) | |
H24 | 0.0314 | 0.3805 | 0.9963 | 0.044* | |
C25 | 0.23617 (19) | 0.39262 (6) | 0.94952 (15) | 0.0345 (3) | |
H25 | 0.2883 | 0.3601 | 1.0030 | 0.041* | |
C26 | 0.31313 (17) | 0.42718 (6) | 0.87426 (14) | 0.0289 (3) | |
H26 | 0.4163 | 0.4173 | 0.8752 | 0.035* | |
C27 | 0.01240 (15) | 0.54319 (6) | 0.73823 (15) | 0.0307 (3) | |
N27 | −0.05056 (16) | 0.58592 (6) | 0.69268 (16) | 0.0436 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0480 (2) | 0.0374 (2) | 0.0645 (3) | 0.00853 (17) | −0.0053 (2) | 0.01587 (19) |
C1 | 0.0278 (6) | 0.0215 (6) | 0.0335 (6) | 0.0000 (5) | 0.0133 (5) | −0.0012 (5) |
N1 | 0.0244 (5) | 0.0223 (5) | 0.0300 (5) | −0.0012 (4) | 0.0088 (4) | 0.0026 (4) |
C2 | 0.0253 (6) | 0.0309 (7) | 0.0335 (7) | −0.0026 (5) | 0.0068 (5) | 0.0059 (5) |
C3 | 0.0277 (6) | 0.0290 (7) | 0.0420 (8) | 0.0009 (5) | 0.0055 (6) | 0.0089 (6) |
N4 | 0.0307 (6) | 0.0234 (5) | 0.0414 (6) | 0.0017 (4) | 0.0054 (5) | 0.0033 (5) |
C5 | 0.0253 (6) | 0.0221 (6) | 0.0342 (7) | −0.0012 (5) | 0.0085 (5) | 0.0008 (5) |
C6 | 0.0345 (7) | 0.0247 (6) | 0.0353 (7) | 0.0020 (5) | 0.0035 (6) | 0.0003 (5) |
C7 | 0.0355 (7) | 0.0286 (7) | 0.0380 (7) | 0.0007 (5) | 0.0051 (6) | −0.0018 (6) |
C8 | 0.0518 (10) | 0.0467 (9) | 0.0396 (8) | −0.0022 (8) | −0.0007 (7) | 0.0015 (7) |
C9 | 0.0557 (11) | 0.0604 (12) | 0.0501 (10) | −0.0142 (9) | −0.0049 (9) | −0.0107 (9) |
C10 | 0.0324 (7) | 0.0416 (8) | 0.0330 (7) | −0.0080 (6) | 0.0060 (6) | 0.0055 (6) |
O10 | 0.0477 (6) | 0.0448 (6) | 0.0376 (6) | −0.0144 (5) | 0.0085 (5) | −0.0036 (5) |
C11 | 0.0256 (6) | 0.0172 (5) | 0.0289 (6) | −0.0001 (4) | 0.0102 (5) | −0.0027 (4) |
C12 | 0.0213 (6) | 0.0260 (6) | 0.0328 (6) | −0.0016 (4) | 0.0055 (5) | −0.0011 (5) |
C13 | 0.0262 (6) | 0.0258 (6) | 0.0259 (6) | 0.0000 (5) | 0.0037 (5) | 0.0007 (5) |
C14 | 0.0247 (6) | 0.0189 (5) | 0.0256 (6) | −0.0001 (4) | 0.0077 (5) | −0.0023 (4) |
C15 | 0.0224 (6) | 0.0280 (6) | 0.0274 (6) | −0.0033 (5) | 0.0049 (5) | −0.0011 (5) |
C16 | 0.0267 (6) | 0.0265 (6) | 0.0259 (6) | −0.0011 (5) | 0.0057 (5) | 0.0009 (5) |
C21 | 0.0276 (6) | 0.0204 (5) | 0.0231 (6) | −0.0029 (5) | 0.0064 (5) | −0.0031 (4) |
C22 | 0.0295 (6) | 0.0233 (6) | 0.0279 (6) | −0.0030 (5) | 0.0094 (5) | −0.0028 (5) |
C23 | 0.0364 (7) | 0.0302 (7) | 0.0359 (7) | −0.0076 (5) | 0.0169 (6) | −0.0047 (5) |
C24 | 0.0547 (9) | 0.0269 (7) | 0.0344 (7) | −0.0109 (6) | 0.0212 (7) | −0.0018 (5) |
C25 | 0.0521 (9) | 0.0225 (6) | 0.0284 (7) | −0.0010 (6) | 0.0106 (6) | 0.0013 (5) |
C26 | 0.0351 (7) | 0.0236 (6) | 0.0271 (6) | 0.0011 (5) | 0.0071 (5) | −0.0010 (5) |
C27 | 0.0251 (6) | 0.0329 (7) | 0.0368 (7) | −0.0007 (5) | 0.0129 (5) | 0.0000 (5) |
N27 | 0.0343 (7) | 0.0416 (7) | 0.0582 (9) | 0.0105 (6) | 0.0182 (6) | 0.0104 (6) |
Geometric parameters (Å, º) top
Cl1—C3 | 1.7179 (14) | C10—H10 | 0.9500 |
C1—N1 | 1.4808 (16) | C11—C12 | 1.3923 (18) |
C1—C11 | 1.5144 (17) | C11—C16 | 1.3952 (17) |
C1—H1A | 0.9900 | C12—C13 | 1.3907 (18) |
C1—H1B | 0.9900 | C12—H12 | 0.9500 |
N1—C5 | 1.3544 (17) | C13—C14 | 1.3980 (17) |
N1—C2 | 1.3969 (17) | C13—H13 | 0.9500 |
C2—C3 | 1.384 (2) | C14—C15 | 1.3990 (18) |
C2—C10 | 1.450 (2) | C14—C21 | 1.4875 (17) |
C3—N4 | 1.3495 (19) | C15—C16 | 1.3876 (18) |
N4—C5 | 1.3401 (17) | C15—H15 | 0.9500 |
C5—C6 | 1.4919 (19) | C16—H16 | 0.9500 |
C6—C7 | 1.5274 (19) | C21—C26 | 1.3990 (18) |
C6—H6A | 0.9900 | C21—C22 | 1.4117 (18) |
C6—H6B | 0.9900 | C22—C23 | 1.4037 (18) |
C7—C8 | 1.502 (2) | C22—C27 | 1.4409 (19) |
C7—H7A | 0.9900 | C23—C24 | 1.382 (2) |
C7—H7B | 0.9900 | C23—H23 | 0.9500 |
C8—C9 | 1.527 (3) | C24—C25 | 1.387 (2) |
C8—H8A | 0.9900 | C24—H24 | 0.9500 |
C8—H8B | 0.9900 | C25—C26 | 1.3922 (19) |
C9—H9A | 0.9800 | C25—H25 | 0.9500 |
C9—H9B | 0.9800 | C26—H26 | 0.9500 |
C9—H9C | 0.9800 | C27—N27 | 1.146 (2) |
C10—O10 | 1.218 (2) | | |
| | | |
N1—C1—C11 | 112.19 (10) | H9B—C9—H9C | 109.5 |
N1—C1—H1A | 109.2 | O10—C10—C2 | 126.44 (14) |
C11—C1—H1A | 109.2 | O10—C10—H10 | 116.8 |
N1—C1—H1B | 109.2 | C2—C10—H10 | 116.8 |
C11—C1—H1B | 109.2 | C12—C11—C16 | 118.83 (11) |
H1A—C1—H1B | 107.9 | C12—C11—C1 | 120.79 (11) |
C5—N1—C2 | 107.39 (11) | C16—C11—C1 | 120.37 (11) |
C5—N1—C1 | 125.69 (11) | C13—C12—C11 | 120.78 (12) |
C2—N1—C1 | 126.91 (11) | C13—C12—H12 | 119.6 |
C3—C2—N1 | 103.43 (12) | C11—C12—H12 | 119.6 |
C3—C2—C10 | 128.72 (13) | C12—C13—C14 | 120.65 (12) |
N1—C2—C10 | 127.83 (13) | C12—C13—H13 | 119.7 |
N4—C3—C2 | 112.82 (12) | C14—C13—H13 | 119.7 |
N4—C3—Cl1 | 120.31 (11) | C13—C14—C15 | 118.23 (11) |
C2—C3—Cl1 | 126.87 (11) | C13—C14—C21 | 120.54 (11) |
C5—N4—C3 | 104.30 (12) | C15—C14—C21 | 121.18 (11) |
N4—C5—N1 | 112.07 (12) | C16—C15—C14 | 121.08 (12) |
N4—C5—C6 | 123.76 (12) | C16—C15—H15 | 119.5 |
N1—C5—C6 | 124.17 (12) | C14—C15—H15 | 119.5 |
C5—C6—C7 | 111.99 (11) | C15—C16—C11 | 120.41 (12) |
C5—C6—H6A | 109.2 | C15—C16—H16 | 119.8 |
C7—C6—H6A | 109.2 | C11—C16—H16 | 119.8 |
C5—C6—H6B | 109.2 | C26—C21—C22 | 117.31 (12) |
C7—C6—H6B | 109.2 | C26—C21—C14 | 120.64 (11) |
H6A—C6—H6B | 107.9 | C22—C21—C14 | 122.04 (11) |
C8—C7—C6 | 114.23 (13) | C23—C22—C21 | 121.30 (12) |
C8—C7—H7A | 108.7 | C23—C22—C27 | 117.60 (12) |
C6—C7—H7A | 108.7 | C21—C22—C27 | 120.98 (11) |
C8—C7—H7B | 108.7 | C24—C23—C22 | 119.78 (13) |
C6—C7—H7B | 108.7 | C24—C23—H23 | 120.1 |
H7A—C7—H7B | 107.6 | C22—C23—H23 | 120.1 |
C7—C8—C9 | 111.80 (15) | C23—C24—C25 | 119.67 (13) |
C7—C8—H8A | 109.3 | C23—C24—H24 | 120.2 |
C9—C8—H8A | 109.3 | C25—C24—H24 | 120.2 |
C7—C8—H8B | 109.3 | C24—C25—C26 | 120.77 (13) |
C9—C8—H8B | 109.3 | C24—C25—H25 | 119.6 |
H8A—C8—H8B | 107.9 | C26—C25—H25 | 119.6 |
C8—C9—H9A | 109.5 | C25—C26—C21 | 121.08 (13) |
C8—C9—H9B | 109.5 | C25—C26—H26 | 119.5 |
H9A—C9—H9B | 109.5 | C21—C26—H26 | 119.5 |
C8—C9—H9C | 109.5 | N27—C27—C22 | 177.30 (15) |
H9A—C9—H9C | 109.5 | | |
| | | |
C11—C1—N1—C5 | 81.09 (15) | C16—C11—C12—C13 | −0.33 (19) |
C11—C1—N1—C2 | −97.27 (15) | C1—C11—C12—C13 | −179.09 (11) |
C5—N1—C2—C3 | 0.15 (14) | C11—C12—C13—C14 | −0.27 (19) |
C1—N1—C2—C3 | 178.75 (12) | C12—C13—C14—C15 | 0.79 (19) |
C5—N1—C2—C10 | 178.88 (13) | C12—C13—C14—C21 | 178.41 (11) |
C1—N1—C2—C10 | −2.5 (2) | C13—C14—C15—C16 | −0.71 (19) |
N1—C2—C3—N4 | −0.11 (16) | C21—C14—C15—C16 | −178.32 (12) |
C10—C2—C3—N4 | −178.82 (14) | C14—C15—C16—C11 | 0.12 (19) |
N1—C2—C3—Cl1 | 179.15 (11) | C12—C11—C16—C15 | 0.40 (19) |
C10—C2—C3—Cl1 | 0.4 (2) | C1—C11—C16—C15 | 179.17 (11) |
C2—C3—N4—C5 | 0.02 (16) | C13—C14—C21—C26 | −40.78 (17) |
Cl1—C3—N4—C5 | −179.29 (10) | C15—C14—C21—C26 | 136.77 (13) |
C3—N4—C5—N1 | 0.08 (15) | C13—C14—C21—C22 | 139.90 (13) |
C3—N4—C5—C6 | 179.70 (13) | C15—C14—C21—C22 | −42.55 (17) |
C2—N1—C5—N4 | −0.15 (15) | C26—C21—C22—C23 | −3.08 (18) |
C1—N1—C5—N4 | −178.77 (11) | C14—C21—C22—C23 | 176.26 (12) |
C2—N1—C5—C6 | −179.76 (12) | C26—C21—C22—C27 | 172.91 (12) |
C1—N1—C5—C6 | 1.6 (2) | C14—C21—C22—C27 | −7.75 (19) |
N4—C5—C6—C7 | −24.01 (19) | C21—C22—C23—C24 | 2.5 (2) |
N1—C5—C6—C7 | 155.57 (13) | C27—C22—C23—C24 | −173.62 (13) |
C5—C6—C7—C8 | −175.75 (14) | C22—C23—C24—C25 | 0.2 (2) |
C6—C7—C8—C9 | 177.47 (16) | C23—C24—C25—C26 | −2.2 (2) |
C3—C2—C10—O10 | −178.75 (15) | C24—C25—C26—C21 | 1.6 (2) |
N1—C2—C10—O10 | 2.8 (2) | C22—C21—C26—C25 | 1.04 (19) |
N1—C1—C11—C12 | −108.39 (13) | C14—C21—C26—C25 | −178.31 (12) |
N1—C1—C11—C16 | 72.87 (15) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1B···O10 | 0.99 | 2.41 | 3.0642 (18) | 123 |
C6—H6A···N27i | 0.99 | 2.56 | 3.5312 (19) | 166 |
Symmetry code: (i) x+1, y, z. |