Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801021389/ww6000sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801021389/ww6000Isup2.hkl |
CCDC reference: 180556
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.008 Å
- R factor = 0.065
- wR factor = 0.190
- Data-to-parameter ratio = 14.2
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 67.24 From the CIF: _reflns_number_total 9044 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 10025 Completeness (_total/calc) 90.21% Alert C: < 95% complete
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
The sample of GBR12909 was obtained from the National Institutes of Health. Crystals were grown at NRL by slow evaporation from a mixture of 2-propanol and ethyl acetate.
GBR12909 crystal exhibit non-merohedral twinning. Program ROTAX, found in the CRYSTALS (Watkin, 2001) suite of programs was used to determine the twin law (-1,0,0/0,1,0/0,0.4,-1). Program ROTWIN (Young, 2001) was used to generate a new reflection file for refinement with SHELXTL (Bruker, 2001). Without twinning the refinement converged at an R factor of 0.094. Adding the single twin reduced the R factor to 0.065.
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).
C28H34Cl2F2N2O | Z = 4 |
Mr = 523.47 | F(000) = 1104 |
Triclinic, P1 | Dx = 1.242 Mg m−3 |
a = 8.5449 (4) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 14.3779 (7) Å | Cell parameters from 5787 reflections |
c = 23.2700 (12) Å | θ = 3.1–61.4° |
α = 83.131 (3)° | µ = 2.38 mm−1 |
β = 80.554 (3)° | T = 293 K |
γ = 89.963 (3)° | Plate, colorless |
V = 2799.4 (2) Å3 | 0.40 × 0.35 × 0.02 mm |
Bruker SMART 6000 diffractometer | 9044 independent reflections |
Radiation source: Rigaku rotating anode | 6598 reflections with I > 2σ(I) |
Gobel mirrors monochromator | Rint = 0.000 |
ω scans | θmax = 67.2°, θmin = 3.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −10→10 |
Tmin = 0.386, Tmax = 0.953 | k = −16→14 |
9044 measured reflections | l = −26→25 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.065 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.190 | w = 1/[σ2(Fo2) + (0.128P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max = 0.047 |
9044 reflections | Δρmax = 0.42 e Å−3 |
635 parameters | Δρmin = −0.26 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0015 (3) |
C28H34Cl2F2N2O | γ = 89.963 (3)° |
Mr = 523.47 | V = 2799.4 (2) Å3 |
Triclinic, P1 | Z = 4 |
a = 8.5449 (4) Å | Cu Kα radiation |
b = 14.3779 (7) Å | µ = 2.38 mm−1 |
c = 23.2700 (12) Å | T = 293 K |
α = 83.131 (3)° | 0.40 × 0.35 × 0.02 mm |
β = 80.554 (3)° |
Bruker SMART 6000 diffractometer | 9044 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 6598 reflections with I > 2σ(I) |
Tmin = 0.386, Tmax = 0.953 | Rint = 0.000 |
9044 measured reflections |
R[F2 > 2σ(F2)] = 0.065 | 0 restraints |
wR(F2) = 0.190 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.97 | Δρmax = 0.42 e Å−3 |
9044 reflections | Δρmin = −0.26 e Å−3 |
635 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.27110 (13) | 0.90445 (7) | 0.47245 (6) | 0.0747 (4) | |
Cl2 | 0.41303 (13) | 1.34098 (8) | 0.32311 (5) | 0.0681 (3) | |
Cl3 | 0.22716 (13) | 0.39355 (8) | 0.52857 (6) | 0.0755 (4) | |
Cl4 | 0.08945 (13) | 0.77499 (8) | 0.67581 (5) | 0.0652 (3) | |
N1 | 0.0308 (3) | 0.5724 (2) | 0.65959 (14) | 0.0508 (8) | |
H1A | 0.0326 | 0.6321 | 0.6688 | 0.061* | |
C2 | 0.1963 (5) | 0.5385 (3) | 0.65222 (19) | 0.0567 (11) | |
H2A | 0.1966 | 0.4735 | 0.6450 | 0.068* | |
H2B | 0.2386 | 0.5421 | 0.6882 | 0.068* | |
C3 | 0.3010 (4) | 0.5957 (3) | 0.60207 (18) | 0.0549 (11) | |
H3A | 0.3098 | 0.6593 | 0.6113 | 0.066* | |
H3B | 0.4064 | 0.5696 | 0.5974 | 0.066* | |
N4 | 0.2384 (3) | 0.5976 (2) | 0.54592 (14) | 0.0482 (8) | |
H4A | 0.2330 | 0.5374 | 0.5379 | 0.058* | |
C5 | 0.0742 (4) | 0.6335 (3) | 0.55385 (18) | 0.0513 (10) | |
H5A | 0.0318 | 0.6329 | 0.5177 | 0.062* | |
H5B | 0.0761 | 0.6978 | 0.5625 | 0.062* | |
C6 | −0.0317 (4) | 0.5752 (3) | 0.60283 (18) | 0.0554 (10) | |
H6A | −0.1373 | 0.6010 | 0.6075 | 0.066* | |
H6B | −0.0396 | 0.5119 | 0.5929 | 0.066* | |
C7 | −0.0783 (5) | 0.5151 (3) | 0.70787 (19) | 0.0618 (11) | |
H7A | −0.1864 | 0.5234 | 0.7007 | 0.074* | |
H7B | −0.0535 | 0.4495 | 0.7064 | 0.074* | |
C8 | −0.0700 (5) | 0.5386 (3) | 0.7682 (2) | 0.0687 (13) | |
H8A | −0.0852 | 0.6053 | 0.7692 | 0.082* | |
H8B | −0.1548 | 0.5055 | 0.7959 | 0.082* | |
O9 | 0.0781 (3) | 0.5137 (2) | 0.78506 (13) | 0.0692 (8) | |
C10 | 0.0713 (5) | 0.5056 (3) | 0.8470 (2) | 0.0681 (12) | |
H10A | 0.0031 | 0.5549 | 0.8623 | 0.082* | |
C1A | 0.2379 (6) | 0.5219 (4) | 0.8596 (2) | 0.0713 (13) | |
C2A | 0.2860 (8) | 0.4809 (5) | 0.9099 (3) | 0.115 (2) | |
H2AA | 0.2176 | 0.4392 | 0.9359 | 0.138* | |
C3A | 0.4356 (9) | 0.5004 (6) | 0.9229 (3) | 0.130 (3) | |
H3AA | 0.4692 | 0.4701 | 0.9562 | 0.156* | |
C4A | 0.5298 (7) | 0.5641 (5) | 0.8860 (3) | 0.0940 (17) | |
F4A | 0.6743 (4) | 0.5850 (3) | 0.89910 (18) | 0.1257 (13) | |
C5A | 0.4898 (6) | 0.6025 (4) | 0.8350 (3) | 0.0777 (14) | |
H5AA | 0.5604 | 0.6424 | 0.8086 | 0.093* | |
C6A | 0.3428 (6) | 0.5820 (3) | 0.8226 (2) | 0.0703 (13) | |
H6AA | 0.3139 | 0.6100 | 0.7878 | 0.084* | |
C1B | −0.0001 (5) | 0.4114 (4) | 0.8757 (2) | 0.0692 (13) | |
C2B | −0.1125 (7) | 0.4034 (4) | 0.9255 (2) | 0.0958 (18) | |
H2BA | −0.1487 | 0.4574 | 0.9414 | 0.115* | |
C3B | −0.1738 (8) | 0.3170 (6) | 0.9528 (3) | 0.110 (2) | |
H3BA | −0.2510 | 0.3126 | 0.9862 | 0.132* | |
C4B | −0.1187 (9) | 0.2398 (5) | 0.9296 (3) | 0.102 (2) | |
F4B | −0.1763 (6) | 0.1556 (3) | 0.95712 (18) | 0.1528 (16) | |
C5B | −0.0096 (8) | 0.2433 (4) | 0.8815 (3) | 0.1020 (19) | |
H5BA | 0.0244 | 0.1884 | 0.8663 | 0.122* | |
C6B | 0.0528 (6) | 0.3288 (4) | 0.8543 (2) | 0.0883 (16) | |
H6BA | 0.1311 | 0.3313 | 0.8212 | 0.106* | |
C11 | 0.3443 (5) | 0.6517 (3) | 0.49536 (18) | 0.0553 (11) | |
H11A | 0.3403 | 0.7176 | 0.5007 | 0.066* | |
H11B | 0.4526 | 0.6319 | 0.4959 | 0.066* | |
C12 | 0.3030 (5) | 0.6407 (3) | 0.4368 (2) | 0.0671 (12) | |
H12A | 0.1979 | 0.6649 | 0.4345 | 0.081* | |
H12B | 0.3015 | 0.5748 | 0.4317 | 0.081* | |
C13 | 0.4235 (6) | 0.6932 (3) | 0.3882 (2) | 0.0742 (13) | |
H13A | 0.4268 | 0.7585 | 0.3948 | 0.089* | |
H13B | 0.5277 | 0.6679 | 0.3908 | 0.089* | |
C1C | 0.3904 (5) | 0.6885 (3) | 0.32774 (19) | 0.0559 (11) | |
C2C | 0.4639 (6) | 0.6252 (3) | 0.2926 (3) | 0.0769 (14) | |
H2CA | 0.5369 | 0.5841 | 0.3066 | 0.092* | |
C3C | 0.4297 (7) | 0.6224 (4) | 0.2364 (3) | 0.0891 (17) | |
H3CA | 0.4848 | 0.5817 | 0.2125 | 0.107* | |
C4C | 0.3174 (7) | 0.6780 (4) | 0.2158 (3) | 0.0900 (16) | |
H4CA | 0.2921 | 0.6742 | 0.1788 | 0.108* | |
C5C | 0.2434 (7) | 0.7388 (4) | 0.2507 (3) | 0.0939 (17) | |
H5CA | 0.1675 | 0.7781 | 0.2370 | 0.113* | |
C6C | 0.2776 (6) | 0.7440 (4) | 0.3054 (2) | 0.0842 (16) | |
H6CA | 0.2232 | 0.7861 | 0.3284 | 0.101* | |
N1' | 0.4683 (3) | 1.1324 (2) | 0.34190 (14) | 0.0516 (8) | |
H1'A | 0.4671 | 1.1956 | 0.3322 | 0.062* | |
C2' | 0.3010 (5) | 1.0963 (3) | 0.3494 (2) | 0.0590 (11) | |
H2'A | 0.2999 | 1.0284 | 0.3569 | 0.071* | |
H2'B | 0.2591 | 1.1136 | 0.3134 | 0.071* | |
C3' | 0.1964 (4) | 1.1350 (3) | 0.39949 (18) | 0.0573 (11) | |
H3'A | 0.1878 | 1.2022 | 0.3899 | 0.069* | |
H3'B | 0.0909 | 1.1073 | 0.4045 | 0.069* | |
N4' | 0.2601 (4) | 1.1156 (2) | 0.45541 (14) | 0.0514 (8) | |
H4'A | 0.2652 | 1.0523 | 0.4636 | 0.062* | |
C5' | 0.4253 (4) | 1.1544 (3) | 0.44745 (18) | 0.0530 (10) | |
H5'A | 0.4677 | 1.1398 | 0.4836 | 0.064* | |
H5'B | 0.4240 | 1.2220 | 0.4386 | 0.064* | |
C6' | 0.5303 (4) | 1.1141 (3) | 0.39856 (18) | 0.0548 (10) | |
H6'A | 0.6361 | 1.1415 | 0.3937 | 0.066* | |
H6'B | 0.5378 | 1.0471 | 0.4089 | 0.066* | |
C7' | 0.5766 (5) | 1.0928 (3) | 0.29382 (19) | 0.0608 (11) | |
H7'A | 0.6844 | 1.0961 | 0.3016 | 0.073* | |
H7'B | 0.5487 | 1.0272 | 0.2948 | 0.073* | |
C8' | 0.5720 (5) | 1.1412 (3) | 0.23349 (19) | 0.0671 (12) | |
H8'A | 0.5947 | 1.2076 | 0.2325 | 0.080* | |
H8'B | 0.6532 | 1.1161 | 0.2056 | 0.080* | |
O9' | 0.4213 (3) | 1.1291 (2) | 0.21703 (14) | 0.0731 (9) | |
C10' | 0.4290 (5) | 1.1425 (4) | 0.1542 (2) | 0.0693 (13) | |
H10B | 0.5032 | 1.1945 | 0.1379 | 0.083* | |
C1A' | 0.2654 (6) | 1.1698 (3) | 0.1416 (2) | 0.0719 (13) | |
C2A' | 0.2335 (8) | 1.1684 (6) | 0.0859 (3) | 0.142 (3) | |
H2AB | 0.3104 | 1.1478 | 0.0573 | 0.170* | |
C3A' | 0.0882 (8) | 1.1973 (7) | 0.0712 (3) | 0.149 (3) | |
H3AB | 0.0676 | 1.1969 | 0.0332 | 0.178* | |
C4A' | −0.0224 (6) | 1.2259 (4) | 0.1138 (3) | 0.0930 (18) | |
F4A' | −0.1672 (4) | 1.2535 (3) | 0.09961 (16) | 0.1190 (12) | |
C5A' | 0.0055 (6) | 1.2304 (3) | 0.1680 (2) | 0.0732 (13) | |
H5AB | −0.0720 | 1.2513 | 0.1963 | 0.088* | |
C6A' | 0.1518 (5) | 1.2034 (3) | 0.1817 (2) | 0.0678 (12) | |
H6AB | 0.1732 | 1.2083 | 0.2191 | 0.081* | |
C1B' | 0.4889 (6) | 1.0560 (4) | 0.1274 (2) | 0.0679 (13) | |
C2B' | 0.4229 (7) | 0.9695 (4) | 0.1495 (2) | 0.0942 (17) | |
H2BB | 0.3407 | 0.9637 | 0.1814 | 0.113* | |
C3B' | 0.4788 (8) | 0.8905 (4) | 0.1242 (3) | 0.106 (2) | |
H3BB | 0.4327 | 0.8319 | 0.1386 | 0.127* | |
C4B' | 0.5998 (9) | 0.8989 (4) | 0.0789 (3) | 0.1005 (19) | |
F4B' | 0.6527 (6) | 0.8212 (3) | 0.05545 (17) | 0.1501 (17) | |
C5B' | 0.6678 (8) | 0.9820 (5) | 0.0564 (2) | 0.1008 (19) | |
H5BB | 0.7507 | 0.9863 | 0.0248 | 0.121* | |
C6B' | 0.6126 (6) | 1.0626 (4) | 0.0812 (2) | 0.0852 (16) | |
H6BB | 0.6598 | 1.1206 | 0.0662 | 0.102* | |
C11' | 0.1544 (5) | 1.1506 (3) | 0.50592 (19) | 0.0576 (11) | |
H11C | 0.0461 | 1.1305 | 0.5057 | 0.069* | |
H11D | 0.1577 | 1.2185 | 0.5003 | 0.069* | |
C12' | 0.1977 (5) | 1.1175 (3) | 0.56468 (19) | 0.0643 (12) | |
H12C | 0.3018 | 1.1423 | 0.5669 | 0.077* | |
H12D | 0.2023 | 1.0496 | 0.5697 | 0.077* | |
C13' | 0.0754 (5) | 1.1496 (4) | 0.6136 (2) | 0.0781 (14) | |
H13C | 0.0670 | 1.2171 | 0.6064 | 0.094* | |
H13D | −0.0271 | 1.1224 | 0.6115 | 0.094* | |
C1C' | 0.1102 (5) | 1.1249 (3) | 0.6738 (2) | 0.0594 (11) | |
C2C' | 0.0399 (6) | 1.0483 (4) | 0.7108 (3) | 0.0792 (14) | |
H2CB | −0.0339 | 1.0116 | 0.6980 | 0.095* | |
C3C' | 0.0766 (7) | 1.0254 (4) | 0.7659 (3) | 0.0884 (17) | |
H3CB | 0.0250 | 0.9749 | 0.7903 | 0.106* | |
C4C' | 0.1874 (7) | 1.0759 (5) | 0.7849 (3) | 0.0946 (18) | |
H4CB | 0.2134 | 1.0596 | 0.8220 | 0.114* | |
C5C' | 0.2597 (7) | 1.1501 (5) | 0.7494 (3) | 0.0985 (18) | |
H5CB | 0.3364 | 1.1849 | 0.7621 | 0.118* | |
C6C' | 0.2211 (6) | 1.1746 (4) | 0.6949 (3) | 0.0851 (16) | |
H6CB | 0.2713 | 1.2264 | 0.6714 | 0.102* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0644 (7) | 0.0477 (6) | 0.1170 (10) | 0.0016 (5) | −0.0350 (7) | −0.0020 (6) |
Cl2 | 0.0604 (7) | 0.0594 (7) | 0.0845 (8) | 0.0051 (5) | −0.0168 (6) | −0.0016 (5) |
Cl3 | 0.0649 (7) | 0.0548 (7) | 0.1176 (10) | 0.0078 (5) | −0.0366 (7) | −0.0239 (6) |
Cl4 | 0.0584 (6) | 0.0620 (7) | 0.0775 (8) | −0.0007 (5) | −0.0134 (6) | −0.0147 (5) |
N1 | 0.0427 (18) | 0.045 (2) | 0.066 (2) | −0.0005 (15) | −0.0140 (17) | −0.0051 (15) |
C2 | 0.049 (2) | 0.057 (3) | 0.066 (3) | 0.010 (2) | −0.017 (2) | −0.003 (2) |
C3 | 0.044 (2) | 0.060 (3) | 0.066 (3) | 0.005 (2) | −0.021 (2) | −0.011 (2) |
N4 | 0.0447 (18) | 0.0421 (19) | 0.061 (2) | 0.0023 (15) | −0.0136 (17) | −0.0112 (15) |
C5 | 0.043 (2) | 0.055 (3) | 0.060 (3) | 0.0072 (19) | −0.018 (2) | −0.0077 (19) |
C6 | 0.041 (2) | 0.062 (3) | 0.066 (3) | −0.001 (2) | −0.018 (2) | −0.007 (2) |
C7 | 0.056 (3) | 0.062 (3) | 0.066 (3) | −0.006 (2) | −0.014 (2) | 0.005 (2) |
C8 | 0.057 (3) | 0.072 (3) | 0.073 (3) | 0.001 (2) | −0.011 (2) | 0.005 (2) |
O9 | 0.0576 (19) | 0.088 (2) | 0.059 (2) | −0.0008 (16) | −0.0110 (16) | 0.0027 (15) |
C10 | 0.065 (3) | 0.078 (3) | 0.060 (3) | 0.000 (3) | −0.009 (2) | −0.003 (2) |
C1A | 0.072 (3) | 0.078 (3) | 0.062 (3) | −0.005 (3) | −0.012 (3) | 0.000 (2) |
C2A | 0.105 (5) | 0.153 (6) | 0.083 (4) | −0.044 (4) | −0.035 (4) | 0.027 (4) |
C3A | 0.129 (6) | 0.161 (7) | 0.104 (5) | −0.038 (6) | −0.061 (5) | 0.029 (5) |
C4A | 0.090 (4) | 0.100 (5) | 0.099 (5) | −0.010 (4) | −0.038 (4) | −0.010 (4) |
F4A | 0.097 (2) | 0.136 (3) | 0.152 (3) | −0.016 (2) | −0.057 (2) | 0.000 (3) |
C5A | 0.069 (3) | 0.070 (3) | 0.093 (4) | 0.007 (3) | −0.009 (3) | −0.012 (3) |
C6A | 0.069 (3) | 0.069 (3) | 0.074 (3) | 0.015 (3) | −0.017 (3) | −0.007 (2) |
C1B | 0.062 (3) | 0.082 (4) | 0.063 (3) | 0.009 (3) | −0.014 (2) | −0.001 (2) |
C2B | 0.097 (4) | 0.096 (4) | 0.083 (4) | 0.004 (3) | 0.007 (3) | 0.002 (3) |
C3B | 0.100 (5) | 0.117 (6) | 0.095 (5) | −0.017 (4) | 0.013 (4) | 0.027 (4) |
C4B | 0.124 (6) | 0.082 (5) | 0.097 (5) | −0.024 (4) | −0.031 (4) | 0.020 (4) |
F4B | 0.190 (4) | 0.116 (3) | 0.140 (3) | −0.045 (3) | −0.036 (3) | 0.047 (3) |
C5B | 0.129 (6) | 0.077 (4) | 0.100 (5) | 0.010 (4) | −0.024 (4) | −0.004 (3) |
C6B | 0.085 (4) | 0.088 (4) | 0.087 (4) | 0.010 (3) | −0.005 (3) | −0.003 (3) |
C11 | 0.046 (2) | 0.044 (2) | 0.074 (3) | −0.0102 (19) | −0.006 (2) | −0.0063 (19) |
C12 | 0.055 (3) | 0.075 (3) | 0.071 (3) | −0.007 (2) | −0.013 (2) | −0.003 (2) |
C13 | 0.065 (3) | 0.067 (3) | 0.086 (4) | −0.010 (2) | −0.007 (3) | 0.000 (2) |
C1C | 0.053 (3) | 0.055 (3) | 0.056 (3) | 0.000 (2) | −0.003 (2) | −0.0025 (19) |
C2C | 0.074 (3) | 0.058 (3) | 0.100 (4) | 0.010 (2) | −0.016 (3) | −0.012 (3) |
C3C | 0.085 (4) | 0.081 (4) | 0.098 (5) | −0.002 (3) | 0.009 (3) | −0.029 (3) |
C4C | 0.101 (4) | 0.088 (4) | 0.078 (4) | −0.023 (4) | −0.013 (3) | 0.001 (3) |
C5C | 0.097 (4) | 0.096 (4) | 0.084 (4) | 0.019 (3) | −0.015 (3) | 0.012 (3) |
C6C | 0.080 (4) | 0.092 (4) | 0.076 (4) | 0.026 (3) | −0.003 (3) | −0.004 (3) |
N1' | 0.0439 (18) | 0.051 (2) | 0.061 (2) | 0.0020 (16) | −0.0127 (17) | −0.0070 (15) |
C2' | 0.050 (2) | 0.060 (3) | 0.070 (3) | −0.002 (2) | −0.020 (2) | −0.007 (2) |
C3' | 0.046 (2) | 0.063 (3) | 0.065 (3) | −0.002 (2) | −0.017 (2) | −0.001 (2) |
N4' | 0.0463 (19) | 0.045 (2) | 0.063 (2) | 0.0022 (15) | −0.0135 (17) | −0.0028 (15) |
C5' | 0.048 (2) | 0.053 (3) | 0.062 (3) | −0.0059 (19) | −0.018 (2) | −0.0081 (19) |
C6' | 0.044 (2) | 0.057 (3) | 0.063 (3) | 0.0005 (19) | −0.015 (2) | −0.0004 (19) |
C7' | 0.053 (3) | 0.063 (3) | 0.069 (3) | 0.007 (2) | −0.012 (2) | −0.017 (2) |
C8' | 0.057 (3) | 0.083 (3) | 0.063 (3) | 0.007 (2) | −0.009 (2) | −0.017 (2) |
O9' | 0.0554 (18) | 0.105 (3) | 0.061 (2) | 0.0018 (17) | −0.0120 (16) | −0.0185 (17) |
C10' | 0.063 (3) | 0.088 (4) | 0.056 (3) | −0.004 (3) | −0.009 (2) | −0.008 (2) |
C1A' | 0.067 (3) | 0.085 (4) | 0.067 (3) | 0.006 (3) | −0.015 (3) | −0.015 (2) |
C2A' | 0.119 (5) | 0.241 (9) | 0.085 (5) | 0.076 (6) | −0.040 (4) | −0.069 (5) |
C3A' | 0.129 (6) | 0.245 (9) | 0.099 (5) | 0.100 (6) | −0.062 (5) | −0.071 (6) |
C4A' | 0.072 (4) | 0.114 (5) | 0.100 (5) | 0.017 (3) | −0.024 (3) | −0.030 (4) |
F4A' | 0.094 (2) | 0.154 (3) | 0.127 (3) | 0.042 (2) | −0.051 (2) | −0.044 (2) |
C5A' | 0.065 (3) | 0.072 (3) | 0.086 (4) | 0.003 (3) | −0.014 (3) | −0.018 (3) |
C6A' | 0.068 (3) | 0.071 (3) | 0.066 (3) | −0.004 (2) | −0.014 (3) | −0.012 (2) |
C1B' | 0.072 (3) | 0.074 (3) | 0.056 (3) | 0.003 (3) | −0.008 (2) | −0.006 (2) |
C2B' | 0.094 (4) | 0.099 (5) | 0.081 (4) | −0.013 (4) | 0.008 (3) | −0.007 (3) |
C3B' | 0.147 (6) | 0.076 (4) | 0.092 (5) | −0.029 (4) | −0.014 (4) | −0.008 (3) |
C4B' | 0.148 (6) | 0.079 (4) | 0.071 (4) | 0.007 (4) | −0.008 (4) | −0.012 (3) |
F4B' | 0.235 (5) | 0.097 (3) | 0.118 (3) | 0.033 (3) | −0.011 (3) | −0.041 (2) |
C5B' | 0.119 (5) | 0.098 (5) | 0.077 (4) | 0.013 (4) | 0.018 (3) | −0.018 (3) |
C6B' | 0.093 (4) | 0.080 (4) | 0.077 (4) | −0.005 (3) | 0.007 (3) | −0.012 (3) |
C11' | 0.047 (2) | 0.052 (3) | 0.074 (3) | 0.005 (2) | −0.008 (2) | −0.013 (2) |
C12' | 0.056 (3) | 0.074 (3) | 0.066 (3) | 0.007 (2) | −0.011 (2) | −0.016 (2) |
C13' | 0.064 (3) | 0.089 (4) | 0.081 (4) | 0.012 (3) | −0.002 (3) | −0.020 (3) |
C1C' | 0.046 (2) | 0.070 (3) | 0.060 (3) | −0.004 (2) | −0.001 (2) | −0.014 (2) |
C2C' | 0.073 (3) | 0.064 (3) | 0.100 (4) | −0.007 (3) | −0.015 (3) | −0.008 (3) |
C3C' | 0.085 (4) | 0.071 (4) | 0.098 (5) | −0.002 (3) | −0.003 (4) | 0.019 (3) |
C4C' | 0.097 (5) | 0.113 (5) | 0.076 (4) | 0.022 (4) | −0.016 (4) | −0.014 (4) |
C5C' | 0.096 (4) | 0.117 (5) | 0.087 (5) | −0.020 (4) | −0.019 (4) | −0.025 (4) |
C6C' | 0.085 (4) | 0.081 (4) | 0.083 (4) | −0.028 (3) | −0.001 (3) | −0.004 (3) |
N1—C2 | 1.486 (5) | N1'—C6' | 1.495 (5) |
N1—C7 | 1.498 (5) | N1'—C2' | 1.497 (5) |
N1—C6 | 1.500 (5) | N1'—C7' | 1.498 (5) |
C2—C3 | 1.505 (6) | C2'—C3' | 1.510 (5) |
C3—N4 | 1.488 (5) | C3'—N4' | 1.487 (5) |
N4—C5 | 1.485 (4) | N4'—C5' | 1.493 (5) |
N4—C11 | 1.498 (5) | N4'—C11' | 1.498 (5) |
C5—C6 | 1.502 (6) | C5'—C6' | 1.502 (5) |
C7—C8 | 1.494 (6) | C7'—C8' | 1.497 (6) |
C8—O9 | 1.418 (5) | C8'—O9' | 1.419 (5) |
O9—C10 | 1.424 (5) | O9'—C10' | 1.441 (5) |
C10—C1B | 1.517 (7) | C10'—C1B' | 1.509 (6) |
C10—C1A | 1.523 (6) | C10'—C1A' | 1.517 (6) |
C1A—C6A | 1.365 (7) | C1A'—C6A' | 1.363 (6) |
C1A—C2A | 1.370 (7) | C1A'—C2A' | 1.370 (7) |
C2A—C3A | 1.397 (8) | C2A'—C3A' | 1.391 (8) |
C3A—C4A | 1.345 (9) | C3A'—C4A' | 1.353 (8) |
C4A—C5A | 1.344 (7) | C4A'—C5A' | 1.332 (7) |
C4A—F4A | 1.361 (6) | C4A'—F4A' | 1.379 (6) |
C5A—C6A | 1.374 (7) | C5A'—C6A' | 1.384 (6) |
C1B—C2B | 1.372 (7) | C1B'—C2B' | 1.372 (7) |
C1B—C6B | 1.389 (7) | C1B'—C6B' | 1.373 (6) |
C2B—C3B | 1.387 (8) | C2B'—C3B' | 1.391 (8) |
C3B—C4B | 1.343 (9) | C3B'—C4B' | 1.344 (8) |
C4B—C5B | 1.330 (8) | C4B'—C5B' | 1.338 (8) |
C4B—F4B | 1.353 (7) | C4B'—F4B' | 1.348 (6) |
C5B—C6B | 1.379 (8) | C5B'—C6B' | 1.402 (7) |
C11—C12 | 1.489 (6) | C11'—C12' | 1.498 (6) |
C12—C13 | 1.525 (6) | C12'—C13' | 1.528 (6) |
C13—C1C | 1.490 (6) | C13'—C1C' | 1.482 (7) |
C1C—C6C | 1.377 (6) | C1C'—C6C' | 1.373 (7) |
C1C—C2C | 1.378 (6) | C1C'—C2C' | 1.385 (7) |
C2C—C3C | 1.392 (7) | C2C'—C3C' | 1.372 (7) |
C3C—C4C | 1.360 (7) | C3C'—C4C' | 1.354 (8) |
C4C—C5C | 1.350 (7) | C4C'—C5C' | 1.352 (8) |
C5C—C6C | 1.364 (7) | C5C'—C6C' | 1.369 (8) |
C2—N1—C7 | 113.1 (3) | C6'—N1'—C2' | 110.2 (3) |
C2—N1—C6 | 110.0 (3) | C6'—N1'—C7' | 110.6 (3) |
C7—N1—C6 | 110.3 (3) | C2'—N1'—C7' | 113.0 (3) |
N1—C2—C3 | 111.5 (3) | N1'—C2'—C3' | 111.6 (3) |
N4—C3—C2 | 112.2 (3) | N4'—C3'—C2' | 111.8 (3) |
C5—N4—C3 | 109.2 (3) | C3'—N4'—C5' | 109.7 (3) |
C5—N4—C11 | 112.3 (3) | C3'—N4'—C11' | 112.4 (3) |
C3—N4—C11 | 112.6 (3) | C5'—N4'—C11' | 112.2 (3) |
N4—C5—C6 | 111.3 (3) | N4'—C5'—C6' | 110.9 (3) |
N1—C6—C5 | 111.4 (3) | N1'—C6'—C5' | 111.8 (3) |
C8—C7—N1 | 114.8 (4) | C8'—C7'—N1' | 114.7 (3) |
O9—C8—C7 | 111.4 (4) | O9'—C8'—C7' | 111.0 (4) |
C8—O9—C10 | 112.2 (3) | C8'—O9'—C10' | 112.1 (3) |
O9—C10—C1B | 110.6 (4) | O9'—C10'—C1B' | 111.0 (4) |
O9—C10—C1A | 108.3 (4) | O9'—C10'—C1A' | 107.9 (4) |
C1B—C10—C1A | 112.7 (4) | C1B'—C10'—C1A' | 112.8 (4) |
C6A—C1A—C2A | 117.2 (5) | C6A'—C1A'—C2A' | 117.7 (5) |
C6A—C1A—C10 | 121.1 (4) | C6A'—C1A'—C10' | 123.1 (4) |
C2A—C1A—C10 | 121.6 (5) | C2A'—C1A'—C10' | 119.0 (5) |
C1A—C2A—C3A | 121.4 (6) | C1A'—C2A'—C3A' | 121.3 (6) |
C4A—C3A—C2A | 118.3 (6) | C4A'—C3A'—C2A' | 118.2 (6) |
C5A—C4A—C3A | 121.9 (6) | C5A'—C4A'—C3A' | 122.4 (6) |
C5A—C4A—F4A | 119.4 (6) | C5A'—C4A'—F4A' | 119.2 (5) |
C3A—C4A—F4A | 118.6 (6) | C3A'—C4A'—F4A' | 118.4 (6) |
C4A—C5A—C6A | 118.9 (6) | C4A'—C5A'—C6A' | 118.8 (5) |
C1A—C6A—C5A | 122.1 (5) | C1A'—C6A'—C5A' | 121.6 (5) |
C2B—C1B—C6B | 117.1 (5) | C2B'—C1B'—C6B' | 119.0 (5) |
C2B—C1B—C10 | 121.8 (5) | C2B'—C1B'—C10' | 120.6 (4) |
C6B—C1B—C10 | 121.0 (5) | C6B'—C1B'—C10' | 120.4 (5) |
C1B—C2B—C3B | 121.8 (6) | C1B'—C2B'—C3B' | 120.0 (5) |
C4B—C3B—C2B | 118.2 (6) | C4B'—C3B'—C2B' | 119.8 (6) |
C5B—C4B—C3B | 122.6 (6) | C5B'—C4B'—C3B' | 121.9 (6) |
C5B—C4B—F4B | 119.4 (7) | C5B'—C4B'—F4B' | 119.4 (6) |
C3B—C4B—F4B | 118.0 (7) | C3B'—C4B'—F4B' | 118.6 (6) |
C4B—C5B—C6B | 119.5 (6) | C4B'—C5B'—C6B' | 119.2 (5) |
C5B—C6B—C1B | 120.7 (5) | C1B'—C6B'—C5B' | 120.2 (5) |
C12—C11—N4 | 114.4 (3) | N4'—C11'—C12' | 114.1 (3) |
C11—C12—C13 | 110.4 (4) | C11'—C12'—C13' | 110.3 (4) |
C1C—C13—C12 | 114.6 (4) | C1C'—C13'—C12' | 115.2 (4) |
C6C—C1C—C2C | 116.7 (4) | C6C'—C1C'—C2C' | 116.2 (5) |
C6C—C1C—C13 | 121.3 (4) | C6C'—C1C'—C13' | 121.3 (5) |
C2C—C1C—C13 | 121.9 (4) | C2C'—C1C'—C13' | 122.4 (4) |
C1C—C2C—C3C | 120.5 (5) | C3C'—C2C'—C1C' | 121.5 (5) |
C4C—C3C—C2C | 121.2 (5) | C4C'—C3C'—C2C' | 120.5 (6) |
C5C—C4C—C3C | 118.1 (6) | C5C'—C4C'—C3C' | 119.3 (6) |
C4C—C5C—C6C | 121.5 (5) | C4C'—C5C'—C6C' | 120.5 (6) |
C5C—C6C—C1C | 121.9 (5) | C5C'—C6C'—C1C' | 122.0 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···Cl4 | 0.91 | 2.14 | 3.034 (3) | 166 |
N4—H4A···Cl3 | 0.91 | 2.11 | 3.012 (3) | 174 |
N1′—H1′A···Cl2 | 0.91 | 2.13 | 3.027 (3) | 167 |
N4′—H4′A···Cl1 | 0.91 | 2.11 | 3.018 (3) | 173 |
Experimental details
Crystal data | |
Chemical formula | C28H34Cl2F2N2O |
Mr | 523.47 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 8.5449 (4), 14.3779 (7), 23.2700 (12) |
α, β, γ (°) | 83.131 (3), 80.554 (3), 89.963 (3) |
V (Å3) | 2799.4 (2) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 2.38 |
Crystal size (mm) | 0.40 × 0.35 × 0.02 |
Data collection | |
Diffractometer | Bruker SMART 6000 diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.386, 0.953 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9044, 9044, 6598 |
Rint | 0.000 |
(sin θ/λ)max (Å−1) | 0.598 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.065, 0.190, 0.97 |
No. of reflections | 9044 |
No. of parameters | 635 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.42, −0.26 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL (Bruker, 2001).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···Cl4 | 0.91 | 2.14 | 3.034 (3) | 166.1 |
N4—H4A···Cl3 | 0.91 | 2.11 | 3.012 (3) | 173.6 |
N1'—H1'A···Cl2 | 0.91 | 2.13 | 3.027 (3) | 166.7 |
N4'—H4'A···Cl1 | 0.91 | 2.11 | 3.018 (3) | 173.1 |
Cocaine is one of the most widely abused drugs in the world. The reinforcing and locomotor stimulating properties of cocaine are said to be mainly mediated by the binding of cocaine to the dopamine transporter (DAT) and subsequent blockade of dopamine reuptake into presynaptic terminals resulting in increased neurotransmission in the mesolimbic dopaminergic system (Kuhar et al., 1991; Rothman et al., 1989). Studies have been aimed at the discovery and development of potent and selective DAT ligands, (Zhang et al., 2000; Newman et al., 1994) that may reduce the effects of cocaine and, therefore, could be used for the treatment of cocaine abuse (Glowa at al., 1995a,b). GBR12909, (I), a potent if not overly selective DAT ligand, is now being examined in man for its toxicity and efficacy prior to exploration of its potential as a cocaine-treatment agent. The X-ray structure of GBR12909 will provide some of the necessary information for structure-activity studies that might lead to a new generation of more potent and selective cocaine-treatment agents.
GBR12909 crystallizes with two molecules per asymmetric unit. The two independent molecules are almost identical with the only difference being the relative twist of the two fluorophenyl groups. The difference between the C1B—C10—C1A—C2A torsion angle and the corresponding torsion in the second molecule in the asymmetric unit is approximately 16°. The central six-membered ring has a normal chair conformation. Both N atoms in the ring are positively charged and hydrogen bond to a Cl ion (see Table 1). There are no other intermolecular interactions. Both aromatic moieties are extended away from the central ring and from each other. The 4-fluorophenyl rings are approximately perpendicular to one another (angle between the ring planes of 88.5 (1) and 88.6 (2)° for the two independent molecules). The third aromatic ring is approximately perpendicular to the plane formed by N4, C11, C12 and C13 [82.3 (3) and 82.2 (2)° for the two independent molecules].