Download citation
Download citation
link to html
The title compound, C22H20ClN3O, (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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805009487/dn6209sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805009487/dn6209Isup2.hkl
Contains datablock I

CCDC reference: 270319

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](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

Computing details top

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
C22H20ClN3OF(000) = 792
Mr = 377.86Dx = 1.298 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 35462 reflections
a = 8.9729 (4) Åθ = 2.4–27.9°
b = 22.6232 (9) ŵ = 0.21 mm1
c = 9.9288 (5) ÅT = 173 K
β = 106.427 (4)°Block, colourless
V = 1933.23 (15) Å30.32 × 0.25 × 0.22 mm
Z = 4
Data collection top
Stoe IPDS-II two-circle
diffractometer
4448 independent reflections
Radiation source: fine-focus sealed tube4037 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
ω scansθmax = 27.7°, θmin = 2.3°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 1111
Tmin = 0.923, Tmax = 0.955k = 2929
31411 measured 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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H-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 parametersΔρmax = 0.51 e Å3
0 restraintsΔρmin = 0.42 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
Cl10.30260 (5)0.815687 (19)0.28852 (5)0.05432 (15)
C10.56545 (15)0.61083 (5)0.46761 (14)0.0266 (3)
H1A0.67880.60770.51220.032*
H1B0.54250.59290.37300.032*
N10.52046 (12)0.67400 (5)0.45370 (12)0.0253 (2)
C20.41095 (15)0.70051 (6)0.34126 (15)0.0303 (3)
C30.41141 (16)0.75900 (6)0.38232 (16)0.0338 (3)
N40.51175 (14)0.76936 (5)0.50970 (13)0.0328 (3)
C50.57655 (15)0.71658 (6)0.55069 (14)0.0272 (3)
C60.69707 (17)0.70626 (6)0.68690 (15)0.0328 (3)
H6A0.77120.67590.67350.039*
H6B0.64650.69090.75640.039*
C70.78594 (17)0.76271 (6)0.74404 (16)0.0351 (3)
H7A0.82870.77960.67080.042*
H7B0.71210.79180.76310.042*
C80.9166 (2)0.75399 (8)0.87568 (18)0.0488 (4)
H8A0.98910.72380.85850.059*
H8B0.87410.73910.95100.059*
C91.0054 (3)0.81133 (9)0.9240 (2)0.0595 (5)
H9A1.08920.80401.01010.089*
H9B0.93430.84110.94250.089*
H9C1.04960.82570.85040.089*
C100.32151 (17)0.67307 (7)0.21157 (16)0.0363 (3)
H100.25510.69820.14390.044*
O100.32308 (14)0.62101 (5)0.18080 (12)0.0441 (3)
C110.48048 (14)0.57667 (5)0.55444 (13)0.0234 (2)
C120.55815 (14)0.55719 (6)0.68901 (14)0.0271 (3)
H120.66540.56590.72730.033*
C130.48063 (15)0.52510 (6)0.76797 (13)0.0267 (3)
H130.53550.51200.85950.032*
C140.32270 (14)0.51194 (5)0.71406 (13)0.0229 (2)
C150.24575 (14)0.53124 (6)0.57833 (13)0.0264 (3)
H150.13870.52230.53950.032*
C160.32321 (15)0.56319 (6)0.49953 (13)0.0267 (3)
H160.26880.57600.40760.032*
C210.24103 (14)0.47628 (5)0.79727 (13)0.0238 (2)
C220.08868 (15)0.48978 (6)0.80110 (14)0.0266 (3)
C230.00994 (17)0.45370 (6)0.87355 (15)0.0328 (3)
H230.09400.46260.87190.039*
C240.0842 (2)0.40516 (6)0.94735 (16)0.0369 (3)
H240.03140.38050.99630.044*
C250.23617 (19)0.39262 (6)0.94952 (15)0.0345 (3)
H250.28830.36011.00300.041*
C260.31313 (17)0.42718 (6)0.87426 (14)0.0289 (3)
H260.41630.41730.87520.035*
C270.01240 (15)0.54319 (6)0.73823 (15)0.0307 (3)
N270.05056 (16)0.58592 (6)0.69268 (16)0.0436 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0480 (2)0.0374 (2)0.0645 (3)0.00853 (17)0.0053 (2)0.01587 (19)
C10.0278 (6)0.0215 (6)0.0335 (6)0.0000 (5)0.0133 (5)0.0012 (5)
N10.0244 (5)0.0223 (5)0.0300 (5)0.0012 (4)0.0088 (4)0.0026 (4)
C20.0253 (6)0.0309 (7)0.0335 (7)0.0026 (5)0.0068 (5)0.0059 (5)
C30.0277 (6)0.0290 (7)0.0420 (8)0.0009 (5)0.0055 (6)0.0089 (6)
N40.0307 (6)0.0234 (5)0.0414 (6)0.0017 (4)0.0054 (5)0.0033 (5)
C50.0253 (6)0.0221 (6)0.0342 (7)0.0012 (5)0.0085 (5)0.0008 (5)
C60.0345 (7)0.0247 (6)0.0353 (7)0.0020 (5)0.0035 (6)0.0003 (5)
C70.0355 (7)0.0286 (7)0.0380 (7)0.0007 (5)0.0051 (6)0.0018 (6)
C80.0518 (10)0.0467 (9)0.0396 (8)0.0022 (8)0.0007 (7)0.0015 (7)
C90.0557 (11)0.0604 (12)0.0501 (10)0.0142 (9)0.0049 (9)0.0107 (9)
C100.0324 (7)0.0416 (8)0.0330 (7)0.0080 (6)0.0060 (6)0.0055 (6)
O100.0477 (6)0.0448 (6)0.0376 (6)0.0144 (5)0.0085 (5)0.0036 (5)
C110.0256 (6)0.0172 (5)0.0289 (6)0.0001 (4)0.0102 (5)0.0027 (4)
C120.0213 (6)0.0260 (6)0.0328 (6)0.0016 (4)0.0055 (5)0.0011 (5)
C130.0262 (6)0.0258 (6)0.0259 (6)0.0000 (5)0.0037 (5)0.0007 (5)
C140.0247 (6)0.0189 (5)0.0256 (6)0.0001 (4)0.0077 (5)0.0023 (4)
C150.0224 (6)0.0280 (6)0.0274 (6)0.0033 (5)0.0049 (5)0.0011 (5)
C160.0267 (6)0.0265 (6)0.0259 (6)0.0011 (5)0.0057 (5)0.0009 (5)
C210.0276 (6)0.0204 (5)0.0231 (6)0.0029 (5)0.0064 (5)0.0031 (4)
C220.0295 (6)0.0233 (6)0.0279 (6)0.0030 (5)0.0094 (5)0.0028 (5)
C230.0364 (7)0.0302 (7)0.0359 (7)0.0076 (5)0.0169 (6)0.0047 (5)
C240.0547 (9)0.0269 (7)0.0344 (7)0.0109 (6)0.0212 (7)0.0018 (5)
C250.0521 (9)0.0225 (6)0.0284 (7)0.0010 (6)0.0106 (6)0.0013 (5)
C260.0351 (7)0.0236 (6)0.0271 (6)0.0011 (5)0.0071 (5)0.0010 (5)
C270.0251 (6)0.0329 (7)0.0368 (7)0.0007 (5)0.0129 (5)0.0000 (5)
N270.0343 (7)0.0416 (7)0.0582 (9)0.0105 (6)0.0182 (6)0.0104 (6)
Geometric parameters (Å, º) top
Cl1—C31.7179 (14)C10—H100.9500
C1—N11.4808 (16)C11—C121.3923 (18)
C1—C111.5144 (17)C11—C161.3952 (17)
C1—H1A0.9900C12—C131.3907 (18)
C1—H1B0.9900C12—H120.9500
N1—C51.3544 (17)C13—C141.3980 (17)
N1—C21.3969 (17)C13—H130.9500
C2—C31.384 (2)C14—C151.3990 (18)
C2—C101.450 (2)C14—C211.4875 (17)
C3—N41.3495 (19)C15—C161.3876 (18)
N4—C51.3401 (17)C15—H150.9500
C5—C61.4919 (19)C16—H160.9500
C6—C71.5274 (19)C21—C261.3990 (18)
C6—H6A0.9900C21—C221.4117 (18)
C6—H6B0.9900C22—C231.4037 (18)
C7—C81.502 (2)C22—C271.4409 (19)
C7—H7A0.9900C23—C241.382 (2)
C7—H7B0.9900C23—H230.9500
C8—C91.527 (3)C24—C251.387 (2)
C8—H8A0.9900C24—H240.9500
C8—H8B0.9900C25—C261.3922 (19)
C9—H9A0.9800C25—H250.9500
C9—H9B0.9800C26—H260.9500
C9—H9C0.9800C27—N271.146 (2)
C10—O101.218 (2)
N1—C1—C11112.19 (10)H9B—C9—H9C109.5
N1—C1—H1A109.2O10—C10—C2126.44 (14)
C11—C1—H1A109.2O10—C10—H10116.8
N1—C1—H1B109.2C2—C10—H10116.8
C11—C1—H1B109.2C12—C11—C16118.83 (11)
H1A—C1—H1B107.9C12—C11—C1120.79 (11)
C5—N1—C2107.39 (11)C16—C11—C1120.37 (11)
C5—N1—C1125.69 (11)C13—C12—C11120.78 (12)
C2—N1—C1126.91 (11)C13—C12—H12119.6
C3—C2—N1103.43 (12)C11—C12—H12119.6
C3—C2—C10128.72 (13)C12—C13—C14120.65 (12)
N1—C2—C10127.83 (13)C12—C13—H13119.7
N4—C3—C2112.82 (12)C14—C13—H13119.7
N4—C3—Cl1120.31 (11)C13—C14—C15118.23 (11)
C2—C3—Cl1126.87 (11)C13—C14—C21120.54 (11)
C5—N4—C3104.30 (12)C15—C14—C21121.18 (11)
N4—C5—N1112.07 (12)C16—C15—C14121.08 (12)
N4—C5—C6123.76 (12)C16—C15—H15119.5
N1—C5—C6124.17 (12)C14—C15—H15119.5
C5—C6—C7111.99 (11)C15—C16—C11120.41 (12)
C5—C6—H6A109.2C15—C16—H16119.8
C7—C6—H6A109.2C11—C16—H16119.8
C5—C6—H6B109.2C26—C21—C22117.31 (12)
C7—C6—H6B109.2C26—C21—C14120.64 (11)
H6A—C6—H6B107.9C22—C21—C14122.04 (11)
C8—C7—C6114.23 (13)C23—C22—C21121.30 (12)
C8—C7—H7A108.7C23—C22—C27117.60 (12)
C6—C7—H7A108.7C21—C22—C27120.98 (11)
C8—C7—H7B108.7C24—C23—C22119.78 (13)
C6—C7—H7B108.7C24—C23—H23120.1
H7A—C7—H7B107.6C22—C23—H23120.1
C7—C8—C9111.80 (15)C23—C24—C25119.67 (13)
C7—C8—H8A109.3C23—C24—H24120.2
C9—C8—H8A109.3C25—C24—H24120.2
C7—C8—H8B109.3C24—C25—C26120.77 (13)
C9—C8—H8B109.3C24—C25—H25119.6
H8A—C8—H8B107.9C26—C25—H25119.6
C8—C9—H9A109.5C25—C26—C21121.08 (13)
C8—C9—H9B109.5C25—C26—H26119.5
H9A—C9—H9B109.5C21—C26—H26119.5
C8—C9—H9C109.5N27—C27—C22177.30 (15)
H9A—C9—H9C109.5
C11—C1—N1—C581.09 (15)C16—C11—C12—C130.33 (19)
C11—C1—N1—C297.27 (15)C1—C11—C12—C13179.09 (11)
C5—N1—C2—C30.15 (14)C11—C12—C13—C140.27 (19)
C1—N1—C2—C3178.75 (12)C12—C13—C14—C150.79 (19)
C5—N1—C2—C10178.88 (13)C12—C13—C14—C21178.41 (11)
C1—N1—C2—C102.5 (2)C13—C14—C15—C160.71 (19)
N1—C2—C3—N40.11 (16)C21—C14—C15—C16178.32 (12)
C10—C2—C3—N4178.82 (14)C14—C15—C16—C110.12 (19)
N1—C2—C3—Cl1179.15 (11)C12—C11—C16—C150.40 (19)
C10—C2—C3—Cl10.4 (2)C1—C11—C16—C15179.17 (11)
C2—C3—N4—C50.02 (16)C13—C14—C21—C2640.78 (17)
Cl1—C3—N4—C5179.29 (10)C15—C14—C21—C26136.77 (13)
C3—N4—C5—N10.08 (15)C13—C14—C21—C22139.90 (13)
C3—N4—C5—C6179.70 (13)C15—C14—C21—C2242.55 (17)
C2—N1—C5—N40.15 (15)C26—C21—C22—C233.08 (18)
C1—N1—C5—N4178.77 (11)C14—C21—C22—C23176.26 (12)
C2—N1—C5—C6179.76 (12)C26—C21—C22—C27172.91 (12)
C1—N1—C5—C61.6 (2)C14—C21—C22—C277.75 (19)
N4—C5—C6—C724.01 (19)C21—C22—C23—C242.5 (2)
N1—C5—C6—C7155.57 (13)C27—C22—C23—C24173.62 (13)
C5—C6—C7—C8175.75 (14)C22—C23—C24—C250.2 (2)
C6—C7—C8—C9177.47 (16)C23—C24—C25—C262.2 (2)
C3—C2—C10—O10178.75 (15)C24—C25—C26—C211.6 (2)
N1—C2—C10—O102.8 (2)C22—C21—C26—C251.04 (19)
N1—C1—C11—C12108.39 (13)C14—C21—C26—C25178.31 (12)
N1—C1—C11—C1672.87 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1B···O100.992.413.0642 (18)123
C6—H6A···N27i0.992.563.5312 (19)166
Symmetry code: (i) x+1, y, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds