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The molecular and crystal structures of the potent and selective lck tyrosine kinase inhibitor, C23H22N4O, have been determined by single-crystal X-ray diffraction. The pyrrolo­pyrimidine and phenyl rings are planar while the cyclo­pentyl ring adopts a conformation between envelope and half-chair. The overall conformation is defined by the spatial arrangement of the ring moieties.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801007917/na6079sup1.cif
Contains datablocks global, plr

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801007917/na6079Isup2.hkl
Contains datablock I

CCDC reference: 170298

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.061
  • wR factor = 0.136
  • Data-to-parameter ratio = 15.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry
Yellow Alert Alert Level C:
PLAT_420 Alert C D-H Without Acceptor N(41) - H(41B) ?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: EXPRESS in CAD-4 Software (Enraf-Nonius, 1989); cell refinement: SET4 and CELDIM in CAD-4 Software; data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1998); software used to prepare material for publication: PLATON.

7-Cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine-4-ylamine top
Crystal data top
C23H22N4OF(000) = 1568
Mr = 370.45Dx = 1.275 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ac 2abCell parameters from 25 reflections
a = 11.914 (2) Åθ = 3.1–10.6°
b = 12.399 (5) ŵ = 0.08 mm1
c = 26.133 (5) ÅT = 293 K
V = 3860.4 (18) Å3Prism, colourless
Z = 80.20 × 0.16 × 0.15 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.000
Radiation source: X-ray tubeθmax = 26.3°, θmin = 2.3°
Graphite monochromatorh = 014
ω/2θ scansk = 150
3910 measured reflectionsl = 032
3910 independent reflections3 standard reflections every 120 min
819 reflections with I > 2σ(I) intensity decay: none
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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136See text
S = 0.84 w = 1/[σ2(Fo2) + (0.0182P)2]
where P = (Fo2 + 2Fc2)/3
3910 reflections(Δ/σ)max = 0.001
253 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.23 e Å3
0 constraints
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'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
xyzUiso*/Ueq
O160.2541 (4)0.1436 (4)0.68577 (16)0.0727 (19)
N10.2088 (4)0.3298 (3)0.52631 (17)0.0390 (17)
N30.2389 (4)0.1407 (4)0.51220 (18)0.0440 (17)
N70.0508 (4)0.3681 (4)0.58142 (18)0.0433 (19)
N410.1340 (4)0.0086 (3)0.54859 (15)0.051 (2)
C20.2611 (4)0.2454 (5)0.5062 (2)0.049 (2)
C40.1503 (5)0.1147 (5)0.5410 (2)0.035 (2)
C50.0086 (5)0.2000 (5)0.5984 (2)0.038 (3)
C60.0265 (4)0.3071 (5)0.6072 (2)0.043 (3)
C80.1191 (5)0.2997 (5)0.5546 (2)0.037 (2)
C90.0834 (5)0.1944 (5)0.5634 (2)0.033 (2)
C100.0740 (5)0.1104 (5)0.6210 (2)0.035 (2)
C110.1189 (4)0.0271 (4)0.5922 (2)0.041 (2)
C120.1759 (4)0.0555 (5)0.6151 (2)0.042 (2)
C130.1929 (5)0.0577 (5)0.6675 (3)0.047 (3)
C140.1537 (5)0.0264 (5)0.6967 (2)0.053 (3)
C150.0930 (5)0.1086 (4)0.6737 (2)0.047 (3)
C170.2673 (6)0.1556 (5)0.7384 (3)0.048 (3)
C180.2003 (6)0.2244 (6)0.7635 (3)0.063 (3)
C190.2193 (6)0.2440 (6)0.8148 (3)0.073 (3)
C200.3041 (7)0.1921 (6)0.8393 (3)0.071 (3)
C210.3716 (6)0.1223 (6)0.8139 (3)0.083 (4)
C220.3536 (7)0.1054 (6)0.7630 (3)0.077 (4)
C710.0632 (5)0.4861 (4)0.5846 (2)0.051 (3)
C720.0838 (6)0.5261 (5)0.6392 (2)0.078 (3)
C730.0152 (7)0.5947 (6)0.6527 (3)0.093 (4)
C740.0557 (6)0.6381 (6)0.6025 (3)0.095 (4)
C750.0411 (5)0.5452 (5)0.5660 (2)0.063 (3)
H20.321600.261400.485000.0580*
H60.083200.334700.627900.0520*
H110.110000.027300.556900.0490*
H120.203900.111400.595000.0510*
H140.167900.028300.731700.0640*
H150.064100.163800.693900.0570*
H180.141600.258600.746600.0750*
H190.174300.292600.832500.0870*
H200.316000.204500.873900.0860*
H210.429100.086500.830900.1000*
H220.400700.059300.744900.0930*
H41A0.179200.037400.535200.0600*
H41B0.078300.013100.566800.0600*
H710.126900.507800.563200.0600*
H72A0.152500.567900.640900.0940*
H72B0.089900.465700.662600.0940*
H73A0.073100.552100.669100.1110*
H73B0.006700.652800.675400.1110*
H74A0.133800.659700.604600.1140*
H74B0.011200.699700.591800.1140*
H75A0.106100.498100.566900.0750*
H75B0.030800.571100.531300.0750*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O160.093 (4)0.080 (3)0.045 (3)0.044 (3)0.003 (3)0.006 (3)
N10.036 (3)0.039 (3)0.042 (3)0.003 (3)0.002 (3)0.006 (3)
N30.043 (3)0.032 (3)0.057 (3)0.000 (3)0.017 (3)0.000 (3)
N70.043 (3)0.027 (3)0.060 (4)0.003 (3)0.011 (3)0.004 (3)
N410.054 (4)0.029 (3)0.069 (4)0.007 (3)0.016 (3)0.003 (3)
C20.042 (4)0.051 (4)0.053 (4)0.006 (4)0.008 (4)0.001 (4)
C40.045 (4)0.028 (4)0.033 (4)0.005 (4)0.011 (3)0.002 (3)
C50.047 (5)0.033 (4)0.034 (4)0.003 (4)0.002 (3)0.003 (4)
C60.031 (4)0.052 (5)0.046 (4)0.007 (4)0.006 (3)0.009 (4)
C80.039 (4)0.033 (4)0.038 (4)0.011 (4)0.001 (4)0.000 (4)
C90.038 (4)0.029 (4)0.031 (4)0.004 (4)0.002 (3)0.004 (3)
C100.033 (4)0.040 (4)0.033 (4)0.005 (4)0.001 (3)0.001 (4)
C110.031 (4)0.048 (4)0.044 (4)0.005 (3)0.007 (3)0.007 (4)
C120.046 (4)0.050 (4)0.031 (4)0.003 (4)0.005 (4)0.008 (4)
C130.044 (5)0.051 (5)0.046 (5)0.007 (4)0.001 (4)0.000 (4)
C140.058 (5)0.063 (5)0.038 (4)0.014 (4)0.001 (4)0.009 (4)
C150.044 (5)0.044 (4)0.054 (5)0.016 (4)0.004 (4)0.008 (4)
C170.060 (6)0.042 (4)0.042 (5)0.025 (4)0.005 (5)0.010 (4)
C180.058 (5)0.077 (6)0.053 (5)0.001 (5)0.000 (4)0.004 (5)
C190.063 (6)0.084 (6)0.072 (6)0.000 (5)0.023 (5)0.027 (5)
C200.063 (6)0.095 (6)0.055 (5)0.037 (5)0.007 (5)0.015 (5)
C210.077 (7)0.106 (7)0.066 (6)0.013 (5)0.005 (5)0.002 (6)
C220.086 (7)0.084 (6)0.062 (6)0.024 (5)0.010 (5)0.013 (5)
C710.053 (5)0.031 (4)0.068 (5)0.001 (4)0.012 (4)0.003 (4)
C720.113 (7)0.046 (5)0.076 (6)0.008 (5)0.033 (6)0.020 (4)
C730.099 (7)0.079 (6)0.100 (7)0.020 (5)0.038 (6)0.030 (6)
C740.091 (6)0.065 (6)0.129 (8)0.027 (5)0.006 (6)0.033 (6)
C750.071 (5)0.047 (4)0.070 (5)0.016 (4)0.009 (5)0.001 (4)
Geometric parameters (Å, º) top
O16—C131.376 (8)C20—C211.355 (11)
O16—C171.392 (9)C21—C221.364 (11)
N1—C21.326 (7)C71—C751.522 (8)
N1—C81.352 (7)C71—C721.530 (8)
N3—C21.334 (8)C72—C731.496 (11)
N3—C41.336 (7)C73—C741.498 (11)
N7—C61.369 (7)C74—C751.506 (10)
N7—C81.368 (8)C2—H20.9305
N7—C711.473 (7)C6—H60.9306
N41—C41.345 (7)C11—H110.9286
N41—H41A0.8589C12—H120.9314
N41—H41B0.8598C14—H140.9305
C4—C91.398 (8)C15—H150.9304
C5—C91.429 (8)C18—H180.9295
C5—C101.480 (8)C19—H190.9298
C5—C61.364 (9)C20—H200.9281
C8—C91.392 (9)C21—H210.9294
C10—C151.396 (7)C22—H220.9302
C10—C111.385 (8)C71—H710.9804
C11—C121.367 (8)C72—H72A0.9698
C12—C131.385 (9)C72—H72B0.9696
C13—C141.374 (9)C73—H73A0.9688
C14—C151.387 (8)C73—H73B0.9690
C17—C181.340 (10)C74—H74A0.9698
C17—C221.363 (11)C74—H74B0.9709
C18—C191.381 (11)C75—H75A0.9702
C19—C201.358 (11)C75—H75B0.9698
O16···C6i3.380 (7)H2···C5xi3.0119
O16···H6i2.4732H6···C153.0505
N1···N41ii2.960 (6)H6···H75A2.5924
N41···C113.230 (7)H6···O16vii2.4732
N41···C103.364 (7)H11···N412.9243
N41···N1iii2.960 (6)H11···H41B2.3132
N1···H75Biv2.8764H11···N41vi2.8071
N1···H20v2.9347H11···H41Avi2.5472
N1···H712.5985H12···N3vi2.8555
N1···H41Aii2.1321H14···C172.5753
N3···H71iii2.6548H14···C222.8831
N3···H12vi2.8555H15···C62.9140
N41···H112.9243H19···C5viii2.8315
N41···H11vi2.8071H19···C9viii2.9325
N41···H71iii2.8741H20···N1viii2.9347
C6···O16vii3.380 (7)H20···C8viii2.9995
C8···C20v3.543 (10)H22···H73Ai2.4350
C10···N413.364 (7)H41A···H11vi2.5472
C11···N413.230 (7)H41A···N1iii2.1321
C14···C223.368 (10)H41A···C2iii2.8867
C20···C8viii3.543 (10)H41A···H71iii2.4872
C22···C143.368 (10)H41B···C52.9555
C2···H41Aii2.8867H41B···C102.7647
C4···H71iii3.0232H41B···C112.4918
C5···H41B2.9555H41B···H112.3132
C5···H19v2.8315H71···N12.5985
C5···H2ix3.0119H71···N3ii2.6548
C6···H75A2.7599H71···N41ii2.8741
C6···H152.9140H71···C4ii3.0232
C6···H72B2.8082H71···H41Aii2.4872
C8···H20v2.9995H72A···C19xii3.0187
C8···H75Biv2.9516H72A···C20xii3.0644
C9···H19v2.9325H72B···C62.8082
C10···H41B2.7647H72B···C19v3.0799
C11···H41B2.4918H73A···H22vii2.4350
C12···H75Ai2.9621H73B···C20xii2.9878
C15···H63.0505H75A···C62.7599
C17···H142.5753H75A···H62.5924
C19···H72Bviii3.0799H75A···C12vii2.9621
C19···H72Ax3.0187H75B···N1iv2.8764
C20···H72Ax3.0644H75B···C8iv2.9516
C20···H73Bx2.9878H75B···C75iv3.0461
C22···H142.8831H75B···H75Biv2.5147
C75···H75Biv3.0461
C13—O16—C17119.0 (5)C71—C75—C74105.1 (5)
C2—N1—C8111.7 (4)N1—C2—H2115.57
C2—N3—C4117.2 (5)N3—C2—H2115.53
C6—N7—C8108.0 (5)N7—C6—H6124.84
C6—N7—C71126.1 (5)C5—C6—H6124.70
C8—N7—C71125.8 (5)C10—C11—H11119.58
H41A—N41—H41B120.11C12—C11—H11119.58
C4—N41—H41A119.94C11—C12—H12119.25
C4—N41—H41B119.96C13—C12—H12119.39
N1—C2—N3128.9 (5)C13—C14—H14120.22
N41—C4—C9123.2 (5)C15—C14—H14120.15
N3—C4—N41115.7 (5)C10—C15—H15119.21
N3—C4—C9121.1 (6)C14—C15—H15119.19
C6—C5—C9106.0 (5)C17—C18—H18120.40
C6—C5—C10125.5 (5)C19—C18—H18120.28
C9—C5—C10128.5 (5)C18—C19—H19120.16
N7—C6—C5110.5 (5)C20—C19—H19120.10
N7—C8—C9108.4 (5)C19—C20—H20119.63
N1—C8—C9126.2 (5)C21—C20—H20119.50
N1—C8—N7125.4 (5)C20—C21—H21120.55
C5—C9—C8107.1 (5)C22—C21—H21120.59
C4—C9—C8114.8 (5)C17—C22—H22119.72
C4—C9—C5137.7 (6)C21—C22—H22119.71
C5—C10—C11123.1 (5)N7—C71—H71108.55
C5—C10—C15119.4 (5)C72—C71—H71108.59
C11—C10—C15117.5 (5)C75—C71—H71108.52
C10—C11—C12120.8 (5)C71—C72—H72A110.56
C11—C12—C13121.4 (5)C71—C72—H72B110.47
O16—C13—C14125.1 (6)C73—C72—H72A110.53
O16—C13—C12115.8 (6)C73—C72—H72B110.45
C12—C13—C14119.0 (6)H72A—C72—H72B108.70
C13—C14—C15119.6 (5)C72—C73—H73A110.83
C10—C15—C14121.6 (5)C72—C73—H73B110.77
C18—C17—C22120.6 (7)C74—C73—H73A110.73
O16—C17—C18119.0 (6)C74—C73—H73B110.85
O16—C17—C22120.2 (6)H73A—C73—H73B109.04
C17—C18—C19119.3 (7)C73—C74—H74A111.02
C18—C19—C20119.7 (7)C73—C74—H74B111.04
C19—C20—C21120.9 (7)C75—C74—H74A110.98
C20—C21—C22118.9 (7)C75—C74—H74B110.87
C17—C22—C21120.6 (7)H74A—C74—H74B108.84
C72—C71—C75105.8 (5)C71—C75—H75A110.74
N7—C71—C72113.0 (4)C71—C75—H75B110.77
N7—C71—C75112.2 (5)C74—C75—H75A110.67
C71—C72—C73106.1 (5)C74—C75—H75B110.71
C72—C73—C74104.6 (6)H75A—C75—H75B108.84
C73—C74—C75104.1 (6)
N1—C8—C9—C5175.5 (5)C6—C5—C9—C82.4 (6)
N7—C8—C9—C4176.0 (5)C10—C5—C9—C46.0 (11)
C6—C5—C10—C11130.1 (6)C9—C5—C6—N72.1 (6)
C6—C5—C10—C1549.4 (8)C10—C5—C9—C8178.1 (5)
C9—C5—C10—C1149.3 (9)N1—C8—C9—C41.3 (8)
C9—C5—C10—C15131.2 (6)N7—C8—C9—C51.8 (6)
C12—C13—O16—C17175.2 (5)C15—C10—C11—C122.4 (8)
C14—C13—O16—C178.3 (9)C5—C10—C15—C14180.0 (9)
C13—O16—C17—C1898.4 (7)C5—C10—C11—C12178.1 (5)
C13—O16—C17—C2287.4 (8)C11—C10—C15—C140.5 (9)
C6—N7—C71—C7257.3 (7)C10—C11—C12—C131.4 (8)
C6—N7—C71—C7562.2 (7)C11—C12—C13—O16178.3 (5)
C8—N7—C71—C72118.3 (6)C11—C12—C13—C141.5 (9)
C8—N7—C71—C75122.1 (6)C12—C13—C14—C153.4 (9)
C2—N1—C8—C90.9 (8)O16—C13—C14—C15179.9 (7)
C8—N1—C2—N32.9 (8)C13—C14—C15—C102.4 (9)
C2—N1—C8—N7177.8 (5)O16—C17—C22—C21175.7 (7)
C4—N3—C2—N12.2 (8)C18—C17—C22—C211.6 (11)
C2—N3—C4—C90.6 (8)O16—C17—C18—C19174.3 (6)
C2—N3—C4—N41176.4 (5)C22—C17—C18—C190.1 (12)
C8—N7—C6—C51.1 (6)C17—C18—C19—C201.1 (11)
C71—N7—C6—C5175.2 (5)C18—C19—C20—C211.0 (12)
C6—N7—C8—N1176.8 (5)C19—C20—C21—C220.5 (12)
C6—N7—C8—C90.5 (6)C20—C21—C22—C171.8 (11)
C71—N7—C8—N10.5 (9)N7—C71—C75—C74140.1 (5)
C71—N7—C8—C9176.8 (5)C72—C71—C75—C7416.4 (6)
N3—C4—C9—C82.1 (8)N7—C71—C72—C73116.2 (6)
N41—C4—C9—C53.0 (11)C75—C71—C72—C737.0 (6)
N41—C4—C9—C8174.7 (5)C71—C72—C73—C7427.9 (7)
N3—C4—C9—C5173.8 (6)C72—C73—C74—C7538.3 (7)
C6—C5—C9—C4174.5 (7)C73—C74—C75—C7133.8 (7)
C10—C5—C6—N7178.4 (5)
Symmetry codes: (i) x+1/2, y1/2, z; (ii) x1/2, y+1/2, z; (iii) x1/2, y1/2, z; (iv) x, y+1, z+1; (v) x, y+1/2, z+3/2; (vi) x, y, z+1; (vii) x+1/2, y+1/2, z; (viii) x, y1/2, z+3/2; (ix) x+1/2, y+1/2, z+1; (x) x+1/2, y1, z+3/2; (xi) x1/2, y+1/2, z+1; (xii) x1/2, y+1, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N41—H41A···N1iii0.862.132.960 (6)162
C6—H6···O16vii0.932.473.380 (7)165
C71—H71···N10.982.603.014 (7)106
Symmetry codes: (iii) x1/2, y1/2, z; (vii) x+1/2, y+1/2, z.
 

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