The quinoline fragment of the title compound, C21H21ClN2O (PK11195), is planar; the dihedral angle between this plane and the chlorophenyl plane is 78.6 (1)°. In the crystal structure, there are two disordered alternative molecules that have different relative stereochemistry of the disordered parts.
Supporting information
CCDC reference: 165641
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- Disorder in main residue
- R factor = 0.069
- wR factor = 0.164
- Data-to-parameter ratio = 12.3
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
PLAT_301 Alert C Main Residue Disorder ........................ 19.00 Perc.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Colourless crystals were grown from an acetone solution by slow evaporation.
The sum of the site-occupancy factors for the disordered fragments was
constrained to unity. The Cl atom of less occupancy was refined isotropically.
Constraints were applied to the geometry (bond lengths and angles), as well as
to the anisotropic displacement parameters of the less occupied fragments.
Data collection: CAD-4 Software(Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: ENPROC (Rettig, 1978); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989).
1-(2-Chlorophenyl)-
N-methyl-
N-(1-methylpropyl)isoquinoline-3-carboxamide
top
Crystal data top
C21H21ClN2O | F(000) = 744 |
Mr = 352.85 | Dx = 1.240 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
a = 10.365 (2) Å | Cell parameters from 25 reflections |
b = 15.529 (4) Å | θ = 11–23° |
c = 11.767 (3) Å | µ = 1.86 mm−1 |
β = 93.33 (2)° | T = 293 K |
V = 1890.8 (8) Å3 | Block, colourless |
Z = 4 | 0.15 × 0.1 × 0.1 mm |
Data collection top
CAD4-F four-circle diffractometer | Rint = 0.074 |
Radiation source: fine-focus sealed tube | θmax = 67.5°, θmin = 4.3° |
Ni-filter monochromator | h = 0→12 |
ω/2θ scans | k = −14→18 |
7214 measured reflections | l = −12→14 |
3385 independent reflections | 2 standard reflections every 33 min |
2278 reflections with I > 2σ(I) | intensity decay: 5% |
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)] = 0.069 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.164 | H-atom parameters constrained |
S = 1.29 | w = 1/[σ2(Fo2) + (0.005P)2 + 0.5P] where P = (Fo2 + 2Fc2)/3 |
3385 reflections | (Δ/σ)max = 0.003 |
276 parameters | Δρmax = 0.64 e Å−3 |
19 restraints | Δρmin = −0.51 e Å−3 |
Crystal data top
C21H21ClN2O | V = 1890.8 (8) Å3 |
Mr = 352.85 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 10.365 (2) Å | µ = 1.86 mm−1 |
b = 15.529 (4) Å | T = 293 K |
c = 11.767 (3) Å | 0.15 × 0.1 × 0.1 mm |
β = 93.33 (2)° | |
Data collection top
CAD4-F four-circle diffractometer | Rint = 0.074 |
7214 measured reflections | 2 standard reflections every 33 min |
3385 independent reflections | intensity decay: 5% |
2278 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.069 | 19 restraints |
wR(F2) = 0.164 | H-atom parameters constrained |
S = 1.29 | Δρmax = 0.64 e Å−3 |
3385 reflections | Δρmin = −0.51 e Å−3 |
276 parameters | |
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 | Occ. (<1) |
C1 | 0.9486 (3) | 0.23215 (18) | 0.4205 (2) | 0.0469 (7) | |
C1' | 0.8930 (3) | 0.1463 (2) | 0.4479 (3) | 0.0564 (8) | |
C2' | 0.8570 (3) | 0.0891 (2) | 0.3638 (3) | 0.0612 (9) | |
H2B | 0.8634 | 0.1049 | 0.2882 | 0.073* | 0.064 (2) |
Cl2A | 0.86755 (12) | 0.11831 (7) | 0.22397 (8) | 0.0801 (4) | 0.936 (2) |
C3' | 0.8107 (4) | 0.0073 (2) | 0.3891 (4) | 0.0853 (13) | |
H3' | 0.7860 | −0.0311 | 0.3312 | 0.102* | |
C4' | 0.8025 (4) | −0.0151 (3) | 0.5000 (5) | 0.0910 (13) | |
H4' | 0.7745 | −0.0701 | 0.5176 | 0.109* | |
C5' | 0.8338 (5) | 0.0403 (3) | 0.5851 (4) | 0.1032 (15) | |
H5' | 0.8251 | 0.0229 | 0.6599 | 0.124* | |
C6' | 0.8797 (3) | 0.1243 (3) | 0.5641 (4) | 0.0957 (15) | |
H6A | 0.9000 | 0.1630 | 0.6228 | 0.115* | 0.936 (2) |
Cl6B | 0.9168 (13) | 0.1953 (7) | 0.6710 (9) | 0.122* | 0.064 (2) |
N2 | 1.0708 (2) | 0.23158 (15) | 0.3962 (2) | 0.0501 (6) | |
C3 | 1.1277 (3) | 0.30875 (19) | 0.3754 (2) | 0.0453 (7) | |
C4 | 1.0654 (3) | 0.38537 (19) | 0.3793 (2) | 0.0472 (7) | |
H4 | 1.1094 | 0.4363 | 0.3662 | 0.057* | |
C4a | 0.9335 (3) | 0.38763 (18) | 0.4033 (2) | 0.0446 (7) | |
C5 | 0.8620 (3) | 0.46484 (19) | 0.4094 (3) | 0.0540 (8) | |
H5 | 0.9021 | 0.5173 | 0.3973 | 0.065* | |
C6 | 0.7356 (3) | 0.4631 (2) | 0.4329 (3) | 0.0605 (8) | |
H6 | 0.6895 | 0.5142 | 0.4370 | 0.073* | |
C7 | 0.6741 (3) | 0.3842 (2) | 0.4510 (3) | 0.0620 (9) | |
H7 | 0.5869 | 0.3834 | 0.4654 | 0.074* | |
C8 | 0.7401 (3) | 0.3093 (2) | 0.4478 (3) | 0.0540 (8) | |
H8 | 0.6980 | 0.2576 | 0.4608 | 0.065* | |
C8a | 0.8725 (3) | 0.30848 (18) | 0.4247 (2) | 0.0441 (7) | |
C31 | 1.2704 (3) | 0.3049 (2) | 0.3562 (3) | 0.0496 (7) | |
O31 | 1.3445 (2) | 0.34467 (16) | 0.4223 (2) | 0.0708 (7) | |
N31 | 1.3089 (2) | 0.2586 (2) | 0.2697 (3) | 0.0685 (9) | |
C32A | 1.2164 (11) | 0.2327 (9) | 0.1757 (11) | 0.076 (4) | 0.624 (9) |
H32A | 1.2606 | 0.1997 | 0.1210 | 0.092* | 0.624 (9) |
H32B | 1.1795 | 0.2832 | 0.1397 | 0.092* | 0.624 (9) |
H32C | 1.1490 | 0.1985 | 0.2054 | 0.092* | 0.624 (9) |
C33A | 1.4472 (7) | 0.2607 (6) | 0.2448 (8) | 0.063 (2) | 0.624 (9) |
H33A | 1.4951 | 0.2772 | 0.3156 | 0.076* | 0.624 (9) |
C34A | 1.4848 (16) | 0.3240 (7) | 0.1547 (15) | 0.102 (4) | 0.624 (9) |
H34A | 1.4576 | 0.3808 | 0.1748 | 0.123* | 0.624 (9) |
H34B | 1.4438 | 0.3081 | 0.0825 | 0.123* | 0.624 (9) |
H34C | 1.5769 | 0.3233 | 0.1497 | 0.123* | 0.624 (9) |
C35A | 1.4883 (8) | 0.1691 (5) | 0.2180 (7) | 0.081 (2) | 0.624 (9) |
H35A | 1.5805 | 0.1687 | 0.2080 | 0.097* | 0.624 (9) |
H35B | 1.4450 | 0.1516 | 0.1463 | 0.097* | 0.624 (9) |
C36A | 1.459 (2) | 0.1030 (7) | 0.3091 (16) | 0.124 (5) | 0.624 (9) |
H36A | 1.4868 | 0.0470 | 0.2862 | 0.149* | 0.624 (9) |
H36B | 1.3672 | 0.1018 | 0.3185 | 0.149* | 0.624 (9) |
H36C | 1.5032 | 0.1185 | 0.3799 | 0.149* | 0.624 (9) |
C32B | 1.2261 (17) | 0.1992 (14) | 0.199 (2) | 0.085 (8) | 0.376 (9) |
H32D | 1.2764 | 0.1734 | 0.1416 | 0.102* | 0.376 (9) |
H32E | 1.1556 | 0.2309 | 0.1624 | 0.102* | 0.376 (9) |
H32F | 1.1929 | 0.1550 | 0.2459 | 0.102* | 0.376 (9) |
C33B | 1.4506 (11) | 0.2290 (9) | 0.2770 (13) | 0.064 (4) | 0.376 (9) |
H33B | 1.4941 | 0.2577 | 0.3429 | 0.077* | 0.376 (9) |
C34B | 1.472 (2) | 0.1334 (11) | 0.291 (3) | 0.124 (10) | 0.376 (9) |
H34D | 1.4351 | 0.1145 | 0.3601 | 0.149* | 0.376 (9) |
H34E | 1.5628 | 0.1214 | 0.2955 | 0.149* | 0.376 (9) |
H34F | 1.4309 | 0.1036 | 0.2275 | 0.149* | 0.376 (9) |
C35B | 1.5071 (12) | 0.2652 (10) | 0.1705 (12) | 0.097 (5) | 0.376 (9) |
H35C | 1.5985 | 0.2514 | 0.1728 | 0.117* | 0.376 (9) |
H35D | 1.4663 | 0.2364 | 0.1046 | 0.117* | 0.376 (9) |
C36B | 1.492 (4) | 0.3609 (13) | 0.154 (3) | 0.155 (13) | 0.376 (9) |
H36D | 1.5289 | 0.3778 | 0.0850 | 0.186* | 0.376 (9) |
H36E | 1.5350 | 0.3904 | 0.2174 | 0.186* | 0.376 (9) |
H36F | 1.4016 | 0.3754 | 0.1506 | 0.186* | 0.376 (9) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0415 (16) | 0.0483 (16) | 0.0516 (18) | −0.0031 (13) | 0.0072 (13) | −0.0017 (13) |
C1' | 0.0427 (17) | 0.0470 (17) | 0.080 (2) | −0.0012 (14) | 0.0105 (15) | 0.0035 (16) |
C2' | 0.057 (2) | 0.0512 (18) | 0.077 (2) | −0.0019 (16) | 0.0192 (17) | 0.0016 (16) |
Cl2A | 0.1093 (9) | 0.0711 (6) | 0.0606 (6) | −0.0157 (6) | 0.0105 (5) | −0.0101 (5) |
C3' | 0.096 (3) | 0.050 (2) | 0.113 (3) | −0.005 (2) | 0.031 (3) | −0.011 (2) |
C4' | 0.096 (3) | 0.070 (3) | 0.109 (4) | −0.013 (2) | 0.025 (3) | 0.020 (3) |
C5' | 0.113 (4) | 0.099 (3) | 0.100 (4) | −0.021 (3) | 0.019 (3) | 0.035 (3) |
C6' | 0.073 (3) | 0.101 (3) | 0.116 (3) | −0.005 (2) | 0.031 (2) | 0.062 (3) |
N2 | 0.0417 (14) | 0.0480 (14) | 0.0615 (16) | −0.0001 (11) | 0.0105 (11) | 0.0022 (11) |
C3 | 0.0371 (15) | 0.0526 (17) | 0.0466 (16) | −0.0034 (13) | 0.0065 (12) | −0.0034 (13) |
C4 | 0.0403 (16) | 0.0483 (16) | 0.0537 (17) | −0.0071 (13) | 0.0088 (13) | −0.0043 (13) |
C4a | 0.0406 (15) | 0.0469 (15) | 0.0464 (16) | −0.0017 (13) | 0.0046 (12) | −0.0035 (12) |
C5 | 0.0530 (19) | 0.0434 (16) | 0.066 (2) | 0.0018 (14) | 0.0049 (15) | −0.0053 (14) |
C6 | 0.0509 (19) | 0.059 (2) | 0.071 (2) | 0.0109 (16) | 0.0046 (16) | −0.0082 (16) |
C7 | 0.0392 (16) | 0.077 (2) | 0.070 (2) | 0.0054 (17) | 0.0081 (14) | −0.0095 (18) |
C8 | 0.0418 (17) | 0.0591 (19) | 0.062 (2) | −0.0070 (15) | 0.0073 (14) | −0.0054 (15) |
C8a | 0.0383 (15) | 0.0485 (16) | 0.0455 (16) | −0.0003 (13) | 0.0031 (12) | −0.0017 (12) |
C31 | 0.0369 (16) | 0.0550 (18) | 0.0573 (19) | −0.0054 (14) | 0.0074 (13) | −0.0029 (14) |
O31 | 0.0451 (13) | 0.0879 (17) | 0.0802 (16) | −0.0133 (12) | 0.0093 (11) | −0.0301 (13) |
N31 | 0.0360 (14) | 0.101 (2) | 0.0692 (19) | −0.0028 (14) | 0.0094 (13) | −0.0330 (16) |
C32A | 0.046 (4) | 0.120 (9) | 0.062 (6) | −0.005 (5) | −0.006 (3) | −0.036 (7) |
C33A | 0.038 (4) | 0.087 (6) | 0.065 (5) | −0.001 (4) | 0.012 (3) | −0.011 (4) |
C34A | 0.083 (7) | 0.095 (8) | 0.134 (10) | −0.006 (7) | 0.056 (7) | 0.027 (8) |
C35A | 0.054 (4) | 0.094 (6) | 0.095 (6) | 0.013 (4) | 0.012 (4) | −0.020 (4) |
C36A | 0.146 (11) | 0.083 (8) | 0.143 (11) | 0.031 (8) | 0.002 (9) | 0.003 (8) |
C32B | 0.042 (7) | 0.142 (19) | 0.072 (10) | 0.007 (9) | 0.020 (7) | −0.023 (11) |
C33B | 0.038 (6) | 0.073 (8) | 0.082 (10) | 0.000 (5) | 0.011 (6) | −0.018 (6) |
C34B | 0.070 (11) | 0.074 (11) | 0.23 (3) | 0.015 (10) | −0.009 (16) | −0.018 (12) |
C35B | 0.054 (7) | 0.157 (15) | 0.083 (9) | −0.025 (9) | 0.018 (6) | −0.027 (9) |
C36B | 0.14 (2) | 0.19 (2) | 0.134 (18) | 0.02 (2) | 0.023 (15) | 0.087 (19) |
Geometric parameters (Å, º) top
C1—N2 | 1.315 (4) | C6—C7 | 1.403 (5) |
C1—C8a | 1.426 (4) | C7—C8 | 1.351 (4) |
C1—C1' | 1.495 (4) | C8—C8a | 1.414 (4) |
C1'—C2' | 1.366 (5) | C3—C31 | 1.510 (4) |
C1'—C6' | 1.423 (5) | C31—O31 | 1.228 (3) |
C2'—C3' | 1.395 (5) | C31—N31 | 1.327 (4) |
C2'—Cl2A | 1.717 (4) | N31—C32A | 1.476 (8) |
C3'—C4' | 1.358 (6) | N31—C33A | 1.479 (7) |
C4'—C5' | 1.345 (6) | N31—C32B | 1.48 (1) |
C5'—C6' | 1.416 (5) | N31—C33B | 1.54 (1) |
C6'—Cl6B | 1.70 (1) | C33A—C34A | 1.51 (1) |
N2—C3 | 1.364 (3) | C33A—C35A | 1.52 (1) |
C3—C4 | 1.356 (4) | C35A—C36A | 1.53 (1) |
C4—C4a | 1.412 (4) | C33B—C34B | 1.51 (2) |
C4a—C8a | 1.412 (4) | C33B—C35B | 1.52 (1) |
C4a—C5 | 1.414 (4) | C35B—C36B | 1.51 (2) |
C5—C6 | 1.355 (4) | | |
| | | |
N2—C1—C8a | 123.7 (3) | C8—C7—C6 | 120.8 (3) |
N2—C1—C1' | 115.4 (3) | C7—C8—C8a | 120.7 (3) |
C8a—C1—C1' | 120.9 (2) | C4a—C8a—C8 | 118.5 (3) |
C2'—C1'—C6' | 120.2 (3) | C4a—C8a—C1 | 117.6 (2) |
C2'—C1'—C1 | 121.1 (3) | C8—C8a—C1 | 124.0 (3) |
C6'—C1'—C1 | 118.7 (3) | O31—C31—N31 | 123.6 (3) |
C1'—C2'—C3' | 121.4 (4) | O31—C31—C3 | 117.8 (3) |
C1'—C2'—Cl2A | 119.5 (3) | N31—C31—C3 | 118.5 (3) |
C3'—C2'—Cl2A | 119.1 (3) | C31—N31—C32A | 120.7 (6) |
C4'—C3'—C2' | 118.6 (4) | C31—N31—C33A | 118.6 (5) |
C5'—C4'—C3' | 121.7 (4) | C32A—N31—C33A | 116.9 (7) |
C4'—C5'—C6' | 121.9 (4) | C31—N31—C32B | 125.4 (9) |
C5'—C6'—C1' | 116.1 (4) | C33A—N31—C32B | 116 (1) |
C5'—C6'—Cl6B | 122.2 (6) | C31—N31—C33B | 116.6 (7) |
C1'—C6'—Cl6B | 121.7 (5) | C32A—N31—C33B | 123 (1) |
C1—N2—C3 | 117.7 (2) | C32B—N31—C33B | 111.4 (9) |
C4—C3—N2 | 123.6 (3) | N31—C33A—C34A | 116.4 (8) |
C4—C3—C31 | 120.9 (3) | N31—C33A—C35A | 107.8 (6) |
N2—C3—C31 | 115.4 (3) | C34A—C33A—C35A | 112.0 (8) |
C3—C4—C4a | 119.8 (3) | C33A—C35A—C36A | 114.3 (8) |
C4—C4a—C8a | 117.6 (3) | C34B—C33B—C35B | 113 (1) |
C4—C4a—C5 | 123.2 (3) | C34B—C33B—N31 | 116 (1) |
C8a—C4a—C5 | 119.2 (3) | C35B—C33B—N31 | 104.8 (8) |
C6—C5—C4a | 120.6 (3) | C36B—C35B—C33B | 115 (1) |
C5—C6—C7 | 120.1 (3) | | |
| | | |
N2—C1—C1'—C2' | −78.3 (4) | C5—C6—C7—C8 | 1.4 (5) |
C8a—C1—C1'—C2' | 103.5 (4) | C6—C7—C8—C8a | −0.7 (5) |
N2—C1—C1'—C6' | 100.9 (3) | C4—C4a—C8a—C8 | −179.4 (3) |
C8a—C1—C1'—C6' | −77.3 (4) | C5—C4a—C8a—C8 | 2.2 (4) |
C6'—C1'—C2'—C3' | −2.2 (5) | C4—C4a—C8a—C1 | 0.0 (4) |
C1—C1'—C2'—C3' | 177.0 (3) | C5—C4a—C8a—C1 | −178.5 (3) |
C6'—C1'—C2'—Cl2A | 177.4 (3) | C7—C8—C8a—C4a | −1.0 (5) |
C1—C1'—C2'—Cl2A | −3.5 (4) | C7—C8—C8a—C1 | 179.6 (3) |
C1'—C2'—C3'—C4' | −0.3 (6) | N2—C1—C8a—C4a | −1.1 (4) |
Cl2A—C2'—C3'—C4' | −179.9 (3) | C1'—C1—C8a—C4a | 176.9 (3) |
C2'—C3'—C4'—C5' | 2.1 (7) | N2—C1—C8a—C8 | 178.2 (3) |
C3'—C4'—C5'—C6' | −1.4 (8) | C1'—C1—C8a—C8 | −3.8 (5) |
C4'—C5'—C6'—C1' | −1.1 (6) | O31—C31—N31—C32A | −162.7 (8) |
C4'—C5'—C6'—Cl6B | 178.8 (6) | C3—C31—N31—C32A | 17.6 (8) |
C2'—C1'—C6'—C5' | 2.8 (5) | O31—C31—N31—C33A | −5.5 (6) |
C1—C1'—C6'—C5' | −176.4 (3) | C3—C31—N31—C33A | 174.9 (4) |
C2'—C1'—C6'—Cl6B | −177.1 (5) | O31—C31—N31—C32B | 170 (1) |
C1—C1'—C6'—Cl6B | 3.7 (4) | C3—C31—N31—C32B | −9 (1) |
C8A—C1—N2—C3 | 0.9 (4) | O31—C31—N31—C33B | 21.2 (7) |
C1'—C1—N2—C3 | −177.2 (3) | C3—C31—N31—C33B | −158.4 (5) |
C1—N2—C3—C4 | 0.4 (4) | C31—N31—C33A—C34A | −95 (1) |
C1—N2—C3—C31 | 175.8 (3) | C32A—N31—C33A—C34A | 63 (1) |
C4—C3—C31—O31 | 56.3 (4) | C31—N31—C33A—C35A | 137.7 (6) |
N2—C3—C31—O31 | −119.2 (3) | C32A—N31—C33A—C35A | −64 (1) |
C4—C3—C31—N31 | −124.0 (3) | N31—C33A—C35A—C36A | −54 (1) |
N2—C3—C31—N31 | 60.5 (4) | C34A—C33A—C35A—C36A | 177 (1) |
N2—C3—C4—C4a | −1.5 (4) | C31—N31—C33B—C34B | 112 (2) |
C31—C3—C4—C4a | −176.7 (3) | C32B—N31—C33B—C34B | −41 (2) |
C3—C4—C4a—C8a | 1.3 (4) | C31—N31—C33B—C35B | −122.6 (9) |
C3—C4—C4a—C5 | 179.6 (3) | C32B—N31—C33B—C35B | 84 (1) |
C4—C4a—C5—C6 | −179.9 (3) | C34B—C33B—C35B—C36B | −178 (2) |
C8a—C4a—C5—C6 | −1.6 (4) | N31—C33B—C35B—C36B | 55 (2) |
C4a—C5—C6—C7 | −0.2 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···Cl2Ai | 0.93 | 3.03 | 3.891 (3) | 154 |
C5—H5···Cl2Ai | 0.93 | 3.25 | 4.064 (3) | 147 |
C6—H6···O31ii | 0.93 | 2.78 | 3.560 (4) | 142 |
C7—H7···O31iii | 0.93 | 2.60 | 3.468 (4) | 155 |
Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) −x+2, −y+1, −z+1; (iii) x−1, y, z. |
Experimental details
Crystal data |
Chemical formula | C21H21ClN2O |
Mr | 352.85 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 10.365 (2), 15.529 (4), 11.767 (3) |
β (°) | 93.33 (2) |
V (Å3) | 1890.8 (8) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 1.86 |
Crystal size (mm) | 0.15 × 0.1 × 0.1 |
|
Data collection |
Diffractometer | CAD4-F four-circle diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7214, 3385, 2278 |
Rint | 0.074 |
(sin θ/λ)max (Å−1) | 0.599 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.069, 0.164, 1.29 |
No. of reflections | 3385 |
No. of parameters | 276 |
No. of restraints | 19 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.64, −0.51 |
Selected torsion angles (º) topN2—C1—C1'—C2' | −78.3 (4) | C32A—N31—C33A—C35A | −64 (1) |
C8a—C1—C1'—C2' | 103.5 (4) | N31—C33A—C35A—C36A | −54 (1) |
N2—C1—C1'—C6' | 100.9 (3) | C34A—C33A—C35A—C36A | 177 (1) |
C8a—C1—C1'—C6' | −77.3 (4) | C31—N31—C33B—C34B | 112 (2) |
C4—C3—C31—N31 | −124.0 (3) | C31—N31—C33B—C35B | −122.6 (9) |
N2—C3—C31—N31 | 60.5 (4) | C34B—C33B—C35B—C36B | −178 (2) |
C3—C31—N31—C33A | 174.9 (4) | N31—C33B—C35B—C36B | 55 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···Cl2Ai | 0.93 | 3.03 | 3.891 (3) | 154.1 |
C5—H5···Cl2Ai | 0.93 | 3.25 | 4.064 (3) | 146.7 |
C6—H6···O31ii | 0.93 | 2.78 | 3.560 (4) | 142.0 |
C7—H7···O31iii | 0.93 | 2.60 | 3.468 (4) | 154.8 |
Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) −x+2, −y+1, −z+1; (iii) x−1, y, z. |
The title compound, PK11195 [(I) in Scheme below], is the first specific non-benzodiazepine ligand which was found to bind the peripheral benzodiazepine receptors with nanomolar affinity (Dubroeucq et al., 1984; LeFur, Perrier et al., 1983; LeFur, Guilloux et al., 1983), and is commonly used as the radioligand for these receptors. Structural, conformational and electronic requirements for recognition and binding processes were widely studied (for example, Cappelli et al. 1997, and references therein).
Here, we report the results of X-ray crystallographic studies of PK11195. Unfortunately, the crystal structure is highly disordered: the methylpropyl substituent was found in two different positions (hereinafter denoted as A and B, Fig. 1) with site-occupation factors of 0.62 (1) and 0.38 (1) for the A and B fragments, respectively. Moreover, the Cl substituent in the chlorophenyl fragment was also found in two positions (2' and 6'), with site-occupation factors of 0.94 (1) and 0.06 (1), respectively.
Both disordered methylpropyl fragments define different relative stereochemistry of the chiral C33 atom. Attempts to refine the structure in a chiral space group P21 gave no significant improvement; the structure could be solved with two different molecules in the asymmetric part of the unit cell, but the refinement was unstable and, what is more important, both independent molecules also showed significant disorder.
Fig. 2 shows a perspective view of the molecule A. The quinoline moiety and the phenyl ring are planar, the maximum deviations from their least-squares planes are 0.019 (3) Å for the former and 0.012 (3) Å for the latter. The dihedral angle between these planes is 78.63 (12)°, close to the value of 74.6° found by molecular mechanics for the receptor-bound molecule (Fiorini et al., 1994). The amide plane C3/C31/O31/N31 makes a dihedral angle of 58.40 (12)° with the quinoline plane.
The crystal packing is mainly determined by van der Waals forces and very weak C—H···Cl and C—H···O interactions.