Download citation
Download citation
link to html
In the title compound, C14H15ClN2O, the benzene and pyrimidine rings are nearly perpendicular, the dihedral angle between them being 84.7 (2)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805017460/is6079sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805017460/is6079Isup2.hkl
Contains datablock I

CCDC reference: 277700

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.055
  • wR factor = 0.134
  • Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C11
Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT301_ALERT_3_C Main Residue Disorder ......................... 14.00 Perc.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 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 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker 1999); software used to prepare material for publication: SHELXTL.

4-(4-tert-Butylphenoxy)-2-chloropyrimidine top
Crystal data top
C14H15ClN2OF(000) = 1104
Mr = 262.73Dx = 1.262 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 602 reflections
a = 20.692 (11) Åθ = 2.2–21.2°
b = 12.456 (6) ŵ = 0.27 mm1
c = 11.792 (6) ÅT = 294 K
β = 114.510 (8)°Block, yellow
V = 2765 (2) Å30.20 × 0.18 × 0.16 mm
Z = 8
Data collection top
Bruker SMART CCD area-detector
diffractometer
2788 independent reflections
Radiation source: fine-focus sealed tube1384 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
φ and ω scansθmax = 26.3°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2525
Tmin = 0.932, Tmax = 0.958k = 915
6731 measured reflectionsl = 1214
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0558P)2 + 0.1813P]
where P = (Fo2 + 2Fc2)/3
2788 reflections(Δ/σ)max = 0.001
182 parametersΔρmax = 0.18 e Å3
21 restraintsΔρmin = 0.20 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*/UeqOcc. (<1)
Cl10.40694 (5)1.22543 (6)0.25627 (7)0.0777 (3)
O10.38020 (12)0.84917 (15)0.31959 (18)0.0769 (7)
N10.39398 (12)1.02521 (17)0.3017 (2)0.0529 (6)
N20.41741 (13)1.14932 (17)0.4668 (2)0.0638 (7)
C10.40606 (14)1.1210 (2)0.3531 (3)0.0517 (7)
C20.41597 (16)1.0671 (2)0.5384 (3)0.0651 (8)
H20.42361.08170.62040.078*
C30.40400 (15)0.9630 (2)0.4990 (3)0.0569 (8)
H30.40350.90720.55110.068*
C40.39272 (14)0.9461 (2)0.3766 (3)0.0512 (7)
C50.37069 (18)0.7597 (2)0.3837 (3)0.0564 (8)
C60.30387 (17)0.7328 (2)0.3701 (3)0.0635 (8)
H60.26540.77640.32400.076*
C70.29395 (15)0.6402 (2)0.4257 (3)0.0570 (8)
H70.24840.62250.41640.068*
C80.34992 (14)0.5727 (2)0.4948 (2)0.0460 (7)
C90.41660 (15)0.6037 (2)0.5063 (3)0.0584 (8)
H90.45540.56070.55230.070*
C100.42759 (16)0.6963 (2)0.4520 (3)0.0636 (8)
H100.47310.71520.46180.076*
C110.33683 (15)0.4698 (2)0.5517 (2)0.0542 (7)
C120.3003 (3)0.4941 (3)0.6372 (5)0.1043 (15)0.87
H12A0.33130.53610.70670.157*0.87
H12B0.28900.42800.66690.157*0.87
H12C0.25730.53360.59200.157*0.87
C130.4038 (2)0.4055 (3)0.6253 (5)0.1038 (15)0.87
H13A0.43520.44760.69430.156*0.87
H13B0.42690.38760.57210.156*0.87
H13C0.39130.34080.65580.156*0.87
C140.2884 (3)0.3951 (3)0.4465 (4)0.1115 (17)0.87
H14A0.24460.43130.39800.167*0.87
H14B0.27870.33110.48210.167*0.87
H14C0.31180.37640.39390.167*0.87
C12'0.3797 (12)0.487 (2)0.6911 (10)0.084 (8)*0.13
H12D0.42940.48840.70930.126*0.13
H12E0.37030.42980.73650.126*0.13
H12F0.36640.55430.71530.126*0.13
C13'0.3649 (14)0.3776 (17)0.503 (3)0.113 (11)*0.13
H13D0.34450.31170.51510.170*0.13
H13E0.41560.37450.54710.170*0.13
H13F0.35240.38790.41570.170*0.13
C14'0.2591 (6)0.453 (2)0.526 (3)0.105 (10)*0.13
H14D0.25530.39810.57950.158*0.13
H14E0.23320.43200.44030.158*0.13
H14F0.23980.51900.54060.158*0.13
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1021 (7)0.0595 (5)0.0724 (6)0.0104 (4)0.0370 (5)0.0079 (4)
O10.131 (2)0.0497 (12)0.0607 (13)0.0141 (11)0.0507 (13)0.0059 (10)
N10.0622 (16)0.0494 (14)0.0475 (14)0.0061 (11)0.0231 (12)0.0029 (12)
N20.0817 (19)0.0556 (15)0.0615 (17)0.0106 (12)0.0371 (15)0.0099 (13)
C10.0490 (18)0.0523 (18)0.055 (2)0.0010 (13)0.0229 (15)0.0013 (15)
C20.079 (2)0.071 (2)0.0504 (19)0.0125 (16)0.0312 (17)0.0101 (17)
C30.070 (2)0.0546 (19)0.0501 (19)0.0068 (14)0.0282 (16)0.0008 (14)
C40.0559 (19)0.0501 (18)0.0497 (18)0.0032 (13)0.0240 (15)0.0039 (14)
C50.081 (2)0.0430 (17)0.0503 (18)0.0033 (16)0.0325 (18)0.0028 (14)
C60.068 (2)0.0557 (18)0.062 (2)0.0172 (16)0.0225 (17)0.0092 (15)
C70.0489 (19)0.0568 (18)0.0633 (19)0.0055 (14)0.0211 (16)0.0065 (15)
C80.0459 (18)0.0483 (16)0.0429 (16)0.0006 (13)0.0174 (14)0.0081 (12)
C90.052 (2)0.0579 (18)0.0586 (19)0.0063 (14)0.0164 (16)0.0029 (15)
C100.057 (2)0.068 (2)0.068 (2)0.0131 (16)0.0289 (18)0.0075 (16)
C110.061 (2)0.0488 (16)0.0493 (17)0.0046 (14)0.0192 (16)0.0031 (14)
C120.154 (5)0.080 (3)0.127 (4)0.019 (3)0.107 (4)0.027 (3)
C130.094 (3)0.084 (3)0.128 (4)0.027 (2)0.041 (3)0.052 (3)
C140.157 (5)0.071 (3)0.084 (3)0.046 (3)0.028 (3)0.004 (2)
Geometric parameters (Å, º) top
Cl1—C11.736 (3)C11—C131.521 (4)
O1—C41.354 (3)C11—C14'1.521 (9)
O1—C51.406 (3)C11—C121.522 (4)
N1—C11.315 (3)C11—C12'1.525 (9)
N1—C41.330 (3)C11—C141.541 (4)
N2—C11.310 (3)C12—H12A0.9600
N2—C21.336 (3)C12—H12B0.9600
C2—C31.365 (3)C12—H12C0.9600
C2—H20.9300C13—H13A0.9600
C3—C41.380 (4)C13—H13B0.9600
C3—H30.9300C13—H13C0.9600
C5—C61.366 (4)C14—H14A0.9600
C5—C101.368 (4)C14—H14B0.9600
C6—C71.383 (3)C14—H14C0.9600
C6—H60.9300C12'—H12D0.9600
C7—C81.389 (4)C12'—H12E0.9600
C7—H70.9300C12'—H12F0.9600
C8—C91.384 (4)C13'—H13D0.9600
C8—C111.523 (3)C13'—H13E0.9600
C9—C101.382 (4)C13'—H13F0.9600
C9—H90.9300C14'—H14D0.9600
C10—H100.9300C14'—H14E0.9600
C11—C13'1.504 (9)C14'—H14F0.9600
C4—O1—C5118.8 (2)C14'—C11—C8113.1 (11)
C1—N1—C4114.8 (2)C12—C11—C8110.6 (2)
C1—N2—C2113.5 (2)C13'—C11—C12'112.1 (10)
N2—C1—N1129.4 (2)C13—C11—C12'58.3 (9)
N2—C1—Cl1115.2 (2)C14'—C11—C12'109.3 (9)
N1—C1—Cl1115.4 (2)C12—C11—C12'59.0 (9)
N2—C2—C3124.2 (3)C8—C11—C12'103.0 (10)
N2—C2—H2117.9C13'—C11—C1457.1 (10)
C3—C2—H2117.9C13—C11—C14106.0 (3)
C2—C3—C4115.4 (3)C14'—C11—C1458.4 (10)
C2—C3—H3122.3C12—C11—C14108.5 (3)
C4—C3—H3122.3C8—C11—C14109.2 (2)
N1—C4—O1112.6 (2)C12'—C11—C14147.8 (10)
N1—C4—C3122.7 (2)C11—C12—H12A109.5
O1—C4—C3124.7 (2)C11—C12—H12B109.5
C6—C5—C10120.6 (3)C11—C12—H12C109.5
C6—C5—O1119.5 (3)C11—C13—H13A109.5
C10—C5—O1119.7 (3)C11—C13—H13B109.5
C5—C6—C7119.4 (3)C11—C13—H13C109.5
C5—C6—H6120.3C11—C14—H14A109.5
C7—C6—H6120.3C11—C14—H14B109.5
C6—C7—C8122.1 (3)C11—C14—H14C109.5
C6—C7—H7119.0C11—C12'—H12D109.5
C8—C7—H7119.0C11—C12'—H12E109.5
C9—C8—C7116.3 (3)H12D—C12'—H12E109.5
C9—C8—C11122.9 (2)C11—C12'—H12F109.5
C7—C8—C11120.7 (2)H12D—C12'—H12F109.5
C10—C9—C8122.4 (3)H12E—C12'—H12F109.5
C10—C9—H9118.8C11—C13'—H13D109.5
C8—C9—H9118.8C11—C13'—H13E109.5
C5—C10—C9119.2 (3)H13D—C13'—H13E109.5
C5—C10—H10120.4C11—C13'—H13F109.5
C9—C10—H10120.4H13D—C13'—H13F109.5
C13'—C11—C1354.0 (10)H13E—C13'—H13F109.5
C13'—C11—C14'111.3 (10)C11—C14'—H14D109.5
C13—C11—C14'132.8 (11)C11—C14'—H14E109.5
C13'—C11—C12141.5 (11)H14D—C14'—H14E109.5
C13—C11—C12108.2 (3)C11—C14'—H14F109.5
C14'—C11—C1252.1 (10)H14D—C14'—H14F109.5
C13'—C11—C8107.9 (11)H14E—C14'—H14F109.5
C13—C11—C8114.1 (3)
C2—N2—C1—N10.2 (4)C6—C7—C8—C11178.3 (2)
C2—N2—C1—Cl1179.7 (2)C7—C8—C9—C100.3 (4)
C4—N1—C1—N20.5 (4)C11—C8—C9—C10178.6 (2)
C4—N1—C1—Cl1179.3 (2)C6—C5—C10—C90.7 (4)
C1—N2—C2—C30.1 (4)O1—C5—C10—C9174.8 (2)
N2—C2—C3—C40.2 (4)C8—C9—C10—C50.4 (4)
C1—N1—C4—O1179.9 (2)C9—C8—C11—C13'56.2 (12)
C1—N1—C4—C30.7 (4)C7—C8—C11—C13'122.6 (12)
C5—O1—C4—N1174.0 (3)C9—C8—C11—C131.6 (4)
C5—O1—C4—C36.8 (4)C7—C8—C11—C13179.6 (3)
C2—C3—C4—N10.6 (4)C9—C8—C11—C14'179.7 (12)
C2—C3—C4—O1179.7 (3)C7—C8—C11—C14'0.9 (12)
C4—O1—C5—C691.2 (3)C9—C8—C11—C12123.8 (3)
C4—O1—C5—C1093.2 (3)C7—C8—C11—C1257.3 (4)
C10—C5—C6—C70.4 (4)C9—C8—C11—C12'62.4 (10)
O1—C5—C6—C7175.2 (2)C7—C8—C11—C12'118.7 (10)
C5—C6—C7—C80.3 (4)C9—C8—C11—C14116.8 (3)
C6—C7—C8—C90.6 (4)C7—C8—C11—C1462.1 (4)
 

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