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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
CCDC reference: 170298
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
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)-7
H-pyrrolo[2,3-
d]pyrimidine-4-ylamine
top
Crystal data top
C23H22N4O | F(000) = 1568 |
Mr = 370.45 | Dx = 1.275 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 25 reflections |
a = 11.914 (2) Å | θ = 3.1–10.6° |
b = 12.399 (5) Å | µ = 0.08 mm−1 |
c = 26.133 (5) Å | T = 293 K |
V = 3860.4 (18) Å3 | Prism, colourless |
Z = 8 | 0.20 × 0.16 × 0.15 mm |
Data collection top
Enraf-Nonius CAD-4 diffractometer | Rint = 0.000 |
Radiation source: X-ray tube | θmax = 26.3°, θmin = 2.3° |
Graphite monochromator | h = 0→14 |
ω/2θ scans | k = −15→0 |
3910 measured reflections | l = 0→32 |
3910 independent reflections | 3 standard reflections every 120 min |
819 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.136 | See text |
S = 0.84 | w = 1/[σ2(Fo2) + (0.0182P)2] where P = (Fo2 + 2Fc2)/3 |
3910 reflections | (Δ/σ)max = 0.001 |
253 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O16 | 0.2541 (4) | −0.1436 (4) | 0.68577 (16) | 0.0727 (19) | |
N1 | −0.2088 (4) | 0.3298 (3) | 0.52631 (17) | 0.0390 (17) | |
N3 | −0.2389 (4) | 0.1407 (4) | 0.51220 (18) | 0.0440 (17) | |
N7 | −0.0508 (4) | 0.3681 (4) | 0.58142 (18) | 0.0433 (19) | |
N41 | −0.1340 (4) | 0.0086 (3) | 0.54859 (15) | 0.051 (2) | |
C2 | −0.2611 (4) | 0.2454 (5) | 0.5062 (2) | 0.049 (2) | |
C4 | −0.1503 (5) | 0.1147 (5) | 0.5410 (2) | 0.035 (2) | |
C5 | 0.0086 (5) | 0.2000 (5) | 0.5984 (2) | 0.038 (3) | |
C6 | 0.0265 (4) | 0.3071 (5) | 0.6072 (2) | 0.043 (3) | |
C8 | −0.1191 (5) | 0.2997 (5) | 0.5546 (2) | 0.037 (2) | |
C9 | −0.0834 (5) | 0.1944 (5) | 0.5634 (2) | 0.033 (2) | |
C10 | 0.0740 (5) | 0.1104 (5) | 0.6210 (2) | 0.035 (2) | |
C11 | 0.1189 (4) | 0.0271 (4) | 0.5922 (2) | 0.041 (2) | |
C12 | 0.1759 (4) | −0.0555 (5) | 0.6151 (2) | 0.042 (2) | |
C13 | 0.1929 (5) | −0.0577 (5) | 0.6675 (3) | 0.047 (3) | |
C14 | 0.1537 (5) | 0.0264 (5) | 0.6967 (2) | 0.053 (3) | |
C15 | 0.0930 (5) | 0.1086 (4) | 0.6737 (2) | 0.047 (3) | |
C17 | 0.2673 (6) | −0.1556 (5) | 0.7384 (3) | 0.048 (3) | |
C18 | 0.2003 (6) | −0.2244 (6) | 0.7635 (3) | 0.063 (3) | |
C19 | 0.2193 (6) | −0.2440 (6) | 0.8148 (3) | 0.073 (3) | |
C20 | 0.3041 (7) | −0.1921 (6) | 0.8393 (3) | 0.071 (3) | |
C21 | 0.3716 (6) | −0.1223 (6) | 0.8139 (3) | 0.083 (4) | |
C22 | 0.3536 (7) | −0.1054 (6) | 0.7630 (3) | 0.077 (4) | |
C71 | −0.0632 (5) | 0.4861 (4) | 0.5846 (2) | 0.051 (3) | |
C72 | −0.0838 (6) | 0.5261 (5) | 0.6392 (2) | 0.078 (3) | |
C73 | 0.0152 (7) | 0.5947 (6) | 0.6527 (3) | 0.093 (4) | |
C74 | 0.0557 (6) | 0.6381 (6) | 0.6025 (3) | 0.095 (4) | |
C75 | 0.0411 (5) | 0.5452 (5) | 0.5660 (2) | 0.063 (3) | |
H2 | −0.32160 | 0.26140 | 0.48500 | 0.0580* | |
H6 | 0.08320 | 0.33470 | 0.62790 | 0.0520* | |
H11 | 0.11000 | 0.02730 | 0.55690 | 0.0490* | |
H12 | 0.20390 | −0.11140 | 0.59500 | 0.0510* | |
H14 | 0.16790 | 0.02830 | 0.73170 | 0.0640* | |
H15 | 0.06410 | 0.16380 | 0.69390 | 0.0570* | |
H18 | 0.14160 | −0.25860 | 0.74660 | 0.0750* | |
H19 | 0.17430 | −0.29260 | 0.83250 | 0.0870* | |
H20 | 0.31600 | −0.20450 | 0.87390 | 0.0860* | |
H21 | 0.42910 | −0.08650 | 0.83090 | 0.1000* | |
H22 | 0.40070 | −0.05930 | 0.74490 | 0.0930* | |
H41A | −0.17920 | −0.03740 | 0.53520 | 0.0600* | |
H41B | −0.07830 | −0.01310 | 0.56680 | 0.0600* | |
H71 | −0.12690 | 0.50780 | 0.56320 | 0.0600* | |
H72A | −0.15250 | 0.56790 | 0.64090 | 0.0940* | |
H72B | −0.08990 | 0.46570 | 0.66260 | 0.0940* | |
H73A | 0.07310 | 0.55210 | 0.66910 | 0.1110* | |
H73B | −0.00670 | 0.65280 | 0.67540 | 0.1110* | |
H74A | 0.13380 | 0.65970 | 0.60460 | 0.1140* | |
H74B | 0.01120 | 0.69970 | 0.59180 | 0.1140* | |
H75A | 0.10610 | 0.49810 | 0.56690 | 0.0750* | |
H75B | 0.03080 | 0.57110 | 0.53130 | 0.0750* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O16 | 0.093 (4) | 0.080 (3) | 0.045 (3) | 0.044 (3) | −0.003 (3) | 0.006 (3) |
N1 | 0.036 (3) | 0.039 (3) | 0.042 (3) | 0.003 (3) | −0.002 (3) | −0.006 (3) |
N3 | 0.043 (3) | 0.032 (3) | 0.057 (3) | 0.000 (3) | −0.017 (3) | 0.000 (3) |
N7 | 0.043 (3) | 0.027 (3) | 0.060 (4) | 0.003 (3) | −0.011 (3) | −0.004 (3) |
N41 | 0.054 (4) | 0.029 (3) | 0.069 (4) | −0.007 (3) | −0.016 (3) | −0.003 (3) |
C2 | 0.042 (4) | 0.051 (4) | 0.053 (4) | 0.006 (4) | −0.008 (4) | 0.001 (4) |
C4 | 0.045 (4) | 0.028 (4) | 0.033 (4) | −0.005 (4) | 0.011 (3) | 0.002 (3) |
C5 | 0.047 (5) | 0.033 (4) | 0.034 (4) | 0.003 (4) | 0.002 (3) | 0.003 (4) |
C6 | 0.031 (4) | 0.052 (5) | 0.046 (4) | −0.007 (4) | −0.006 (3) | −0.009 (4) |
C8 | 0.039 (4) | 0.033 (4) | 0.038 (4) | −0.011 (4) | 0.001 (4) | 0.000 (4) |
C9 | 0.038 (4) | 0.029 (4) | 0.031 (4) | −0.004 (4) | 0.002 (3) | −0.004 (3) |
C10 | 0.033 (4) | 0.040 (4) | 0.033 (4) | −0.005 (4) | 0.001 (3) | 0.001 (4) |
C11 | 0.031 (4) | 0.048 (4) | 0.044 (4) | 0.005 (3) | −0.007 (3) | 0.007 (4) |
C12 | 0.046 (4) | 0.050 (4) | 0.031 (4) | 0.003 (4) | 0.005 (4) | −0.008 (4) |
C13 | 0.044 (5) | 0.051 (5) | 0.046 (5) | 0.007 (4) | 0.001 (4) | 0.000 (4) |
C14 | 0.058 (5) | 0.063 (5) | 0.038 (4) | 0.014 (4) | −0.001 (4) | −0.009 (4) |
C15 | 0.044 (5) | 0.044 (4) | 0.054 (5) | 0.016 (4) | 0.004 (4) | −0.008 (4) |
C17 | 0.060 (6) | 0.042 (4) | 0.042 (5) | 0.025 (4) | 0.005 (5) | 0.010 (4) |
C18 | 0.058 (5) | 0.077 (6) | 0.053 (5) | 0.001 (5) | 0.000 (4) | 0.004 (5) |
C19 | 0.063 (6) | 0.084 (6) | 0.072 (6) | 0.000 (5) | 0.023 (5) | 0.027 (5) |
C20 | 0.063 (6) | 0.095 (6) | 0.055 (5) | 0.037 (5) | −0.007 (5) | 0.015 (5) |
C21 | 0.077 (7) | 0.106 (7) | 0.066 (6) | −0.013 (5) | −0.005 (5) | 0.002 (6) |
C22 | 0.086 (7) | 0.084 (6) | 0.062 (6) | −0.024 (5) | 0.010 (5) | 0.013 (5) |
C71 | 0.053 (5) | 0.031 (4) | 0.068 (5) | −0.001 (4) | −0.012 (4) | −0.003 (4) |
C72 | 0.113 (7) | 0.046 (5) | 0.076 (6) | −0.008 (5) | 0.033 (6) | −0.020 (4) |
C73 | 0.099 (7) | 0.079 (6) | 0.100 (7) | 0.020 (5) | −0.038 (6) | −0.030 (6) |
C74 | 0.091 (6) | 0.065 (6) | 0.129 (8) | −0.027 (5) | 0.006 (6) | −0.033 (6) |
C75 | 0.071 (5) | 0.047 (4) | 0.070 (5) | −0.016 (4) | 0.009 (5) | −0.001 (4) |
Geometric parameters (Å, º) top
O16—C13 | 1.376 (8) | C20—C21 | 1.355 (11) |
O16—C17 | 1.392 (9) | C21—C22 | 1.364 (11) |
N1—C2 | 1.326 (7) | C71—C75 | 1.522 (8) |
N1—C8 | 1.352 (7) | C71—C72 | 1.530 (8) |
N3—C2 | 1.334 (8) | C72—C73 | 1.496 (11) |
N3—C4 | 1.336 (7) | C73—C74 | 1.498 (11) |
N7—C6 | 1.369 (7) | C74—C75 | 1.506 (10) |
N7—C8 | 1.368 (8) | C2—H2 | 0.9305 |
N7—C71 | 1.473 (7) | C6—H6 | 0.9306 |
N41—C4 | 1.345 (7) | C11—H11 | 0.9286 |
N41—H41A | 0.8589 | C12—H12 | 0.9314 |
N41—H41B | 0.8598 | C14—H14 | 0.9305 |
C4—C9 | 1.398 (8) | C15—H15 | 0.9304 |
C5—C9 | 1.429 (8) | C18—H18 | 0.9295 |
C5—C10 | 1.480 (8) | C19—H19 | 0.9298 |
C5—C6 | 1.364 (9) | C20—H20 | 0.9281 |
C8—C9 | 1.392 (9) | C21—H21 | 0.9294 |
C10—C15 | 1.396 (7) | C22—H22 | 0.9302 |
C10—C11 | 1.385 (8) | C71—H71 | 0.9804 |
C11—C12 | 1.367 (8) | C72—H72A | 0.9698 |
C12—C13 | 1.385 (9) | C72—H72B | 0.9696 |
C13—C14 | 1.374 (9) | C73—H73A | 0.9688 |
C14—C15 | 1.387 (8) | C73—H73B | 0.9690 |
C17—C18 | 1.340 (10) | C74—H74A | 0.9698 |
C17—C22 | 1.363 (11) | C74—H74B | 0.9709 |
C18—C19 | 1.381 (11) | C75—H75A | 0.9702 |
C19—C20 | 1.358 (11) | C75—H75B | 0.9698 |
| | | |
O16···C6i | 3.380 (7) | H2···C5xi | 3.0119 |
O16···H6i | 2.4732 | H6···C15 | 3.0505 |
N1···N41ii | 2.960 (6) | H6···H75A | 2.5924 |
N41···C11 | 3.230 (7) | H6···O16vii | 2.4732 |
N41···C10 | 3.364 (7) | H11···N41 | 2.9243 |
N41···N1iii | 2.960 (6) | H11···H41B | 2.3132 |
N1···H75Biv | 2.8764 | H11···N41vi | 2.8071 |
N1···H20v | 2.9347 | H11···H41Avi | 2.5472 |
N1···H71 | 2.5985 | H12···N3vi | 2.8555 |
N1···H41Aii | 2.1321 | H14···C17 | 2.5753 |
N3···H71iii | 2.6548 | H14···C22 | 2.8831 |
N3···H12vi | 2.8555 | H15···C6 | 2.9140 |
N41···H11 | 2.9243 | H19···C5viii | 2.8315 |
N41···H11vi | 2.8071 | H19···C9viii | 2.9325 |
N41···H71iii | 2.8741 | H20···N1viii | 2.9347 |
C6···O16vii | 3.380 (7) | H20···C8viii | 2.9995 |
C8···C20v | 3.543 (10) | H22···H73Ai | 2.4350 |
C10···N41 | 3.364 (7) | H41A···H11vi | 2.5472 |
C11···N41 | 3.230 (7) | H41A···N1iii | 2.1321 |
C14···C22 | 3.368 (10) | H41A···C2iii | 2.8867 |
C20···C8viii | 3.543 (10) | H41A···H71iii | 2.4872 |
C22···C14 | 3.368 (10) | H41B···C5 | 2.9555 |
C2···H41Aii | 2.8867 | H41B···C10 | 2.7647 |
C4···H71iii | 3.0232 | H41B···C11 | 2.4918 |
C5···H41B | 2.9555 | H41B···H11 | 2.3132 |
C5···H19v | 2.8315 | H71···N1 | 2.5985 |
C5···H2ix | 3.0119 | H71···N3ii | 2.6548 |
C6···H75A | 2.7599 | H71···N41ii | 2.8741 |
C6···H15 | 2.9140 | H71···C4ii | 3.0232 |
C6···H72B | 2.8082 | H71···H41Aii | 2.4872 |
C8···H20v | 2.9995 | H72A···C19xii | 3.0187 |
C8···H75Biv | 2.9516 | H72A···C20xii | 3.0644 |
C9···H19v | 2.9325 | H72B···C6 | 2.8082 |
C10···H41B | 2.7647 | H72B···C19v | 3.0799 |
C11···H41B | 2.4918 | H73A···H22vii | 2.4350 |
C12···H75Ai | 2.9621 | H73B···C20xii | 2.9878 |
C15···H6 | 3.0505 | H75A···C6 | 2.7599 |
C17···H14 | 2.5753 | H75A···H6 | 2.5924 |
C19···H72Bviii | 3.0799 | H75A···C12vii | 2.9621 |
C19···H72Ax | 3.0187 | H75B···N1iv | 2.8764 |
C20···H72Ax | 3.0644 | H75B···C8iv | 2.9516 |
C20···H73Bx | 2.9878 | H75B···C75iv | 3.0461 |
C22···H14 | 2.8831 | H75B···H75Biv | 2.5147 |
C75···H75Biv | 3.0461 | | |
| | | |
C13—O16—C17 | 119.0 (5) | C71—C75—C74 | 105.1 (5) |
C2—N1—C8 | 111.7 (4) | N1—C2—H2 | 115.57 |
C2—N3—C4 | 117.2 (5) | N3—C2—H2 | 115.53 |
C6—N7—C8 | 108.0 (5) | N7—C6—H6 | 124.84 |
C6—N7—C71 | 126.1 (5) | C5—C6—H6 | 124.70 |
C8—N7—C71 | 125.8 (5) | C10—C11—H11 | 119.58 |
H41A—N41—H41B | 120.11 | C12—C11—H11 | 119.58 |
C4—N41—H41A | 119.94 | C11—C12—H12 | 119.25 |
C4—N41—H41B | 119.96 | C13—C12—H12 | 119.39 |
N1—C2—N3 | 128.9 (5) | C13—C14—H14 | 120.22 |
N41—C4—C9 | 123.2 (5) | C15—C14—H14 | 120.15 |
N3—C4—N41 | 115.7 (5) | C10—C15—H15 | 119.21 |
N3—C4—C9 | 121.1 (6) | C14—C15—H15 | 119.19 |
C6—C5—C9 | 106.0 (5) | C17—C18—H18 | 120.40 |
C6—C5—C10 | 125.5 (5) | C19—C18—H18 | 120.28 |
C9—C5—C10 | 128.5 (5) | C18—C19—H19 | 120.16 |
N7—C6—C5 | 110.5 (5) | C20—C19—H19 | 120.10 |
N7—C8—C9 | 108.4 (5) | C19—C20—H20 | 119.63 |
N1—C8—C9 | 126.2 (5) | C21—C20—H20 | 119.50 |
N1—C8—N7 | 125.4 (5) | C20—C21—H21 | 120.55 |
C5—C9—C8 | 107.1 (5) | C22—C21—H21 | 120.59 |
C4—C9—C8 | 114.8 (5) | C17—C22—H22 | 119.72 |
C4—C9—C5 | 137.7 (6) | C21—C22—H22 | 119.71 |
C5—C10—C11 | 123.1 (5) | N7—C71—H71 | 108.55 |
C5—C10—C15 | 119.4 (5) | C72—C71—H71 | 108.59 |
C11—C10—C15 | 117.5 (5) | C75—C71—H71 | 108.52 |
C10—C11—C12 | 120.8 (5) | C71—C72—H72A | 110.56 |
C11—C12—C13 | 121.4 (5) | C71—C72—H72B | 110.47 |
O16—C13—C14 | 125.1 (6) | C73—C72—H72A | 110.53 |
O16—C13—C12 | 115.8 (6) | C73—C72—H72B | 110.45 |
C12—C13—C14 | 119.0 (6) | H72A—C72—H72B | 108.70 |
C13—C14—C15 | 119.6 (5) | C72—C73—H73A | 110.83 |
C10—C15—C14 | 121.6 (5) | C72—C73—H73B | 110.77 |
C18—C17—C22 | 120.6 (7) | C74—C73—H73A | 110.73 |
O16—C17—C18 | 119.0 (6) | C74—C73—H73B | 110.85 |
O16—C17—C22 | 120.2 (6) | H73A—C73—H73B | 109.04 |
C17—C18—C19 | 119.3 (7) | C73—C74—H74A | 111.02 |
C18—C19—C20 | 119.7 (7) | C73—C74—H74B | 111.04 |
C19—C20—C21 | 120.9 (7) | C75—C74—H74A | 110.98 |
C20—C21—C22 | 118.9 (7) | C75—C74—H74B | 110.87 |
C17—C22—C21 | 120.6 (7) | H74A—C74—H74B | 108.84 |
C72—C71—C75 | 105.8 (5) | C71—C75—H75A | 110.74 |
N7—C71—C72 | 113.0 (4) | C71—C75—H75B | 110.77 |
N7—C71—C75 | 112.2 (5) | C74—C75—H75A | 110.67 |
C71—C72—C73 | 106.1 (5) | C74—C75—H75B | 110.71 |
C72—C73—C74 | 104.6 (6) | H75A—C75—H75B | 108.84 |
C73—C74—C75 | 104.1 (6) | | |
| | | |
N1—C8—C9—C5 | −175.5 (5) | C6—C5—C9—C8 | −2.4 (6) |
N7—C8—C9—C4 | 176.0 (5) | C10—C5—C9—C4 | 6.0 (11) |
C6—C5—C10—C11 | −130.1 (6) | C9—C5—C6—N7 | 2.1 (6) |
C6—C5—C10—C15 | 49.4 (8) | C10—C5—C9—C8 | 178.1 (5) |
C9—C5—C10—C11 | 49.3 (9) | N1—C8—C9—C4 | −1.3 (8) |
C9—C5—C10—C15 | −131.2 (6) | N7—C8—C9—C5 | 1.8 (6) |
C12—C13—O16—C17 | −175.2 (5) | C15—C10—C11—C12 | 2.4 (8) |
C14—C13—O16—C17 | 8.3 (9) | C5—C10—C15—C14 | 180.0 (9) |
C13—O16—C17—C18 | 98.4 (7) | C5—C10—C11—C12 | −178.1 (5) |
C13—O16—C17—C22 | −87.4 (8) | C11—C10—C15—C14 | −0.5 (9) |
C6—N7—C71—C72 | −57.3 (7) | C10—C11—C12—C13 | −1.4 (8) |
C6—N7—C71—C75 | 62.2 (7) | C11—C12—C13—O16 | −178.3 (5) |
C8—N7—C71—C72 | 118.3 (6) | C11—C12—C13—C14 | −1.5 (9) |
C8—N7—C71—C75 | −122.1 (6) | C12—C13—C14—C15 | 3.4 (9) |
C2—N1—C8—C9 | −0.9 (8) | O16—C13—C14—C15 | 179.9 (7) |
C8—N1—C2—N3 | 2.9 (8) | C13—C14—C15—C10 | −2.4 (9) |
C2—N1—C8—N7 | −177.8 (5) | O16—C17—C22—C21 | −175.7 (7) |
C4—N3—C2—N1 | −2.2 (8) | C18—C17—C22—C21 | −1.6 (11) |
C2—N3—C4—C9 | −0.6 (8) | O16—C17—C18—C19 | 174.3 (6) |
C2—N3—C4—N41 | 176.4 (5) | C22—C17—C18—C19 | 0.1 (12) |
C8—N7—C6—C5 | −1.1 (6) | C17—C18—C19—C20 | 1.1 (11) |
C71—N7—C6—C5 | 175.2 (5) | C18—C19—C20—C21 | −1.0 (12) |
C6—N7—C8—N1 | 176.8 (5) | C19—C20—C21—C22 | −0.5 (12) |
C6—N7—C8—C9 | −0.5 (6) | C20—C21—C22—C17 | 1.8 (11) |
C71—N7—C8—N1 | 0.5 (9) | N7—C71—C75—C74 | −140.1 (5) |
C71—N7—C8—C9 | −176.8 (5) | C72—C71—C75—C74 | −16.4 (6) |
N3—C4—C9—C8 | 2.1 (8) | N7—C71—C72—C73 | 116.2 (6) |
N41—C4—C9—C5 | −3.0 (11) | C75—C71—C72—C73 | −7.0 (6) |
N41—C4—C9—C8 | −174.7 (5) | C71—C72—C73—C74 | 27.9 (7) |
N3—C4—C9—C5 | 173.8 (6) | C72—C73—C74—C75 | −38.3 (7) |
C6—C5—C9—C4 | −174.5 (7) | C73—C74—C75—C71 | 33.8 (7) |
C10—C5—C6—N7 | −178.4 (5) | | |
Symmetry codes: (i) −x+1/2, y−1/2, z; (ii) −x−1/2, y+1/2, z; (iii) −x−1/2, y−1/2, 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, y−1/2, −z+3/2; (ix) x+1/2, −y+1/2, −z+1; (x) x+1/2, y−1, −z+3/2; (xi) x−1/2, −y+1/2, −z+1; (xii) x−1/2, y+1, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N41—H41A···N1iii | 0.86 | 2.13 | 2.960 (6) | 162 |
C6—H6···O16vii | 0.93 | 2.47 | 3.380 (7) | 165 |
C71—H71···N1 | 0.98 | 2.60 | 3.014 (7) | 106 |
Symmetry codes: (iii) −x−1/2, y−1/2, z; (vii) −x+1/2, y+1/2, z. |
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