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GBR12909, C28H34F2N2O, is one of the earliest agents found to have high affinity and selectivity for the dop­amine transporter (DAT). The triclinic crystal, of the hydro­chloride salt of GBR12909, C28H34F2N2O2+·2Cl-, exhibited non-merohedral twinning.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801021389/ww6000sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801021389/ww6000Isup2.hkl
Contains datablock I

CCDC reference: 180556

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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


Yellow Alert 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

Comment top

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].

Experimental top

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.

Refinement top

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.

Computing details top

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).

Figures top
[Figure 1] Fig. 1. View of GBR12909 with 20% probability ellipsoids showing one of the two independent molecules in the asymmetric unit.
[Figure 2] Fig. 2. The asymmetric unit showing each independent molecule hydrogen bonded to two Cl atoms.
(I) top
Crystal data top
C28H34Cl2F2N2OZ = 4
Mr = 523.47F(000) = 1104
Triclinic, P1Dx = 1.242 Mg m3
a = 8.5449 (4) ÅCu Kα radiation, λ = 1.54178 Å
b = 14.3779 (7) ÅCell parameters from 5787 reflections
c = 23.2700 (12) Åθ = 3.1–61.4°
α = 83.131 (3)°µ = 2.38 mm1
β = 80.554 (3)°T = 293 K
γ = 89.963 (3)°Plate, colorless
V = 2799.4 (2) Å30.40 × 0.35 × 0.02 mm
Data collection top
Bruker SMART 6000
diffractometer
9044 independent reflections
Radiation source: Rigaku rotating anode6598 reflections with I > 2σ(I)
Gobel mirrors monochromatorRint = 0.000
ω scansθmax = 67.2°, θmin = 3.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1010
Tmin = 0.386, Tmax = 0.953k = 1614
9044 measured reflectionsl = 2625
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.065H 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 reflectionsΔρmax = 0.42 e Å3
635 parametersΔρmin = 0.26 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0015 (3)
Crystal data top
C28H34Cl2F2N2Oγ = 89.963 (3)°
Mr = 523.47V = 2799.4 (2) Å3
Triclinic, P1Z = 4
a = 8.5449 (4) ÅCu Kα radiation
b = 14.3779 (7) ŵ = 2.38 mm1
c = 23.2700 (12) ÅT = 293 K
α = 83.131 (3)°0.40 × 0.35 × 0.02 mm
β = 80.554 (3)°
Data collection top
Bruker SMART 6000
diffractometer
9044 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
6598 reflections with I > 2σ(I)
Tmin = 0.386, Tmax = 0.953Rint = 0.000
9044 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0650 restraints
wR(F2) = 0.190H atoms treated by a mixture of independent and constrained refinement
S = 0.97Δρmax = 0.42 e Å3
9044 reflectionsΔρmin = 0.26 e Å3
635 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.27110 (13)0.90445 (7)0.47245 (6)0.0747 (4)
Cl20.41303 (13)1.34098 (8)0.32311 (5)0.0681 (3)
Cl30.22716 (13)0.39355 (8)0.52857 (6)0.0755 (4)
Cl40.08945 (13)0.77499 (8)0.67581 (5)0.0652 (3)
N10.0308 (3)0.5724 (2)0.65959 (14)0.0508 (8)
H1A0.03260.63210.66880.061*
C20.1963 (5)0.5385 (3)0.65222 (19)0.0567 (11)
H2A0.19660.47350.64500.068*
H2B0.23860.54210.68820.068*
C30.3010 (4)0.5957 (3)0.60207 (18)0.0549 (11)
H3A0.30980.65930.61130.066*
H3B0.40640.56960.59740.066*
N40.2384 (3)0.5976 (2)0.54592 (14)0.0482 (8)
H4A0.23300.53740.53790.058*
C50.0742 (4)0.6335 (3)0.55385 (18)0.0513 (10)
H5A0.03180.63290.51770.062*
H5B0.07610.69780.56250.062*
C60.0317 (4)0.5752 (3)0.60283 (18)0.0554 (10)
H6A0.13730.60100.60750.066*
H6B0.03960.51190.59290.066*
C70.0783 (5)0.5151 (3)0.70787 (19)0.0618 (11)
H7A0.18640.52340.70070.074*
H7B0.05350.44950.70640.074*
C80.0700 (5)0.5386 (3)0.7682 (2)0.0687 (13)
H8A0.08520.60530.76920.082*
H8B0.15480.50550.79590.082*
O90.0781 (3)0.5137 (2)0.78506 (13)0.0692 (8)
C100.0713 (5)0.5056 (3)0.8470 (2)0.0681 (12)
H10A0.00310.55490.86230.082*
C1A0.2379 (6)0.5219 (4)0.8596 (2)0.0713 (13)
C2A0.2860 (8)0.4809 (5)0.9099 (3)0.115 (2)
H2AA0.21760.43920.93590.138*
C3A0.4356 (9)0.5004 (6)0.9229 (3)0.130 (3)
H3AA0.46920.47010.95620.156*
C4A0.5298 (7)0.5641 (5)0.8860 (3)0.0940 (17)
F4A0.6743 (4)0.5850 (3)0.89910 (18)0.1257 (13)
C5A0.4898 (6)0.6025 (4)0.8350 (3)0.0777 (14)
H5AA0.56040.64240.80860.093*
C6A0.3428 (6)0.5820 (3)0.8226 (2)0.0703 (13)
H6AA0.31390.61000.78780.084*
C1B0.0001 (5)0.4114 (4)0.8757 (2)0.0692 (13)
C2B0.1125 (7)0.4034 (4)0.9255 (2)0.0958 (18)
H2BA0.14870.45740.94140.115*
C3B0.1738 (8)0.3170 (6)0.9528 (3)0.110 (2)
H3BA0.25100.31260.98620.132*
C4B0.1187 (9)0.2398 (5)0.9296 (3)0.102 (2)
F4B0.1763 (6)0.1556 (3)0.95712 (18)0.1528 (16)
C5B0.0096 (8)0.2433 (4)0.8815 (3)0.1020 (19)
H5BA0.02440.18840.86630.122*
C6B0.0528 (6)0.3288 (4)0.8543 (2)0.0883 (16)
H6BA0.13110.33130.82120.106*
C110.3443 (5)0.6517 (3)0.49536 (18)0.0553 (11)
H11A0.34030.71760.50070.066*
H11B0.45260.63190.49590.066*
C120.3030 (5)0.6407 (3)0.4368 (2)0.0671 (12)
H12A0.19790.66490.43450.081*
H12B0.30150.57480.43170.081*
C130.4235 (6)0.6932 (3)0.3882 (2)0.0742 (13)
H13A0.42680.75850.39480.089*
H13B0.52770.66790.39080.089*
C1C0.3904 (5)0.6885 (3)0.32774 (19)0.0559 (11)
C2C0.4639 (6)0.6252 (3)0.2926 (3)0.0769 (14)
H2CA0.53690.58410.30660.092*
C3C0.4297 (7)0.6224 (4)0.2364 (3)0.0891 (17)
H3CA0.48480.58170.21250.107*
C4C0.3174 (7)0.6780 (4)0.2158 (3)0.0900 (16)
H4CA0.29210.67420.17880.108*
C5C0.2434 (7)0.7388 (4)0.2507 (3)0.0939 (17)
H5CA0.16750.77810.23700.113*
C6C0.2776 (6)0.7440 (4)0.3054 (2)0.0842 (16)
H6CA0.22320.78610.32840.101*
N1'0.4683 (3)1.1324 (2)0.34190 (14)0.0516 (8)
H1'A0.46711.19560.33220.062*
C2'0.3010 (5)1.0963 (3)0.3494 (2)0.0590 (11)
H2'A0.29991.02840.35690.071*
H2'B0.25911.11360.31340.071*
C3'0.1964 (4)1.1350 (3)0.39949 (18)0.0573 (11)
H3'A0.18781.20220.38990.069*
H3'B0.09091.10730.40450.069*
N4'0.2601 (4)1.1156 (2)0.45541 (14)0.0514 (8)
H4'A0.26521.05230.46360.062*
C5'0.4253 (4)1.1544 (3)0.44745 (18)0.0530 (10)
H5'A0.46771.13980.48360.064*
H5'B0.42401.22200.43860.064*
C6'0.5303 (4)1.1141 (3)0.39856 (18)0.0548 (10)
H6'A0.63611.14150.39370.066*
H6'B0.53781.04710.40890.066*
C7'0.5766 (5)1.0928 (3)0.29382 (19)0.0608 (11)
H7'A0.68441.09610.30160.073*
H7'B0.54871.02720.29480.073*
C8'0.5720 (5)1.1412 (3)0.23349 (19)0.0671 (12)
H8'A0.59471.20760.23250.080*
H8'B0.65321.11610.20560.080*
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)
H10B0.50321.19450.13790.083*
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)
H2AB0.31041.14780.05730.170*
C3A'0.0882 (8)1.1973 (7)0.0712 (3)0.149 (3)
H3AB0.06761.19690.03320.178*
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)
H5AB0.07201.25130.19630.088*
C6A'0.1518 (5)1.2034 (3)0.1817 (2)0.0678 (12)
H6AB0.17321.20830.21910.081*
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)
H2BB0.34070.96370.18140.113*
C3B'0.4788 (8)0.8905 (4)0.1242 (3)0.106 (2)
H3BB0.43270.83190.13860.127*
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)
H5BB0.75070.98630.02480.121*
C6B'0.6126 (6)1.0626 (4)0.0812 (2)0.0852 (16)
H6BB0.65981.12060.06620.102*
C11'0.1544 (5)1.1506 (3)0.50592 (19)0.0576 (11)
H11C0.04611.13050.50570.069*
H11D0.15771.21850.50030.069*
C12'0.1977 (5)1.1175 (3)0.56468 (19)0.0643 (12)
H12C0.30181.14230.56690.077*
H12D0.20231.04960.56970.077*
C13'0.0754 (5)1.1496 (4)0.6136 (2)0.0781 (14)
H13C0.06701.21710.60640.094*
H13D0.02711.12240.61150.094*
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)
H2CB0.03391.01160.69800.095*
C3C'0.0766 (7)1.0254 (4)0.7659 (3)0.0884 (17)
H3CB0.02500.97490.79030.106*
C4C'0.1874 (7)1.0759 (5)0.7849 (3)0.0946 (18)
H4CB0.21341.05960.82200.114*
C5C'0.2597 (7)1.1501 (5)0.7494 (3)0.0985 (18)
H5CB0.33641.18490.76210.118*
C6C'0.2211 (6)1.1746 (4)0.6949 (3)0.0851 (16)
H6CB0.27131.22640.67140.102*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0644 (7)0.0477 (6)0.1170 (10)0.0016 (5)0.0350 (7)0.0020 (6)
Cl20.0604 (7)0.0594 (7)0.0845 (8)0.0051 (5)0.0168 (6)0.0016 (5)
Cl30.0649 (7)0.0548 (7)0.1176 (10)0.0078 (5)0.0366 (7)0.0239 (6)
Cl40.0584 (6)0.0620 (7)0.0775 (8)0.0007 (5)0.0134 (6)0.0147 (5)
N10.0427 (18)0.045 (2)0.066 (2)0.0005 (15)0.0140 (17)0.0051 (15)
C20.049 (2)0.057 (3)0.066 (3)0.010 (2)0.017 (2)0.003 (2)
C30.044 (2)0.060 (3)0.066 (3)0.005 (2)0.021 (2)0.011 (2)
N40.0447 (18)0.0421 (19)0.061 (2)0.0023 (15)0.0136 (17)0.0112 (15)
C50.043 (2)0.055 (3)0.060 (3)0.0072 (19)0.018 (2)0.0077 (19)
C60.041 (2)0.062 (3)0.066 (3)0.001 (2)0.018 (2)0.007 (2)
C70.056 (3)0.062 (3)0.066 (3)0.006 (2)0.014 (2)0.005 (2)
C80.057 (3)0.072 (3)0.073 (3)0.001 (2)0.011 (2)0.005 (2)
O90.0576 (19)0.088 (2)0.059 (2)0.0008 (16)0.0110 (16)0.0027 (15)
C100.065 (3)0.078 (3)0.060 (3)0.000 (3)0.009 (2)0.003 (2)
C1A0.072 (3)0.078 (3)0.062 (3)0.005 (3)0.012 (3)0.000 (2)
C2A0.105 (5)0.153 (6)0.083 (4)0.044 (4)0.035 (4)0.027 (4)
C3A0.129 (6)0.161 (7)0.104 (5)0.038 (6)0.061 (5)0.029 (5)
C4A0.090 (4)0.100 (5)0.099 (5)0.010 (4)0.038 (4)0.010 (4)
F4A0.097 (2)0.136 (3)0.152 (3)0.016 (2)0.057 (2)0.000 (3)
C5A0.069 (3)0.070 (3)0.093 (4)0.007 (3)0.009 (3)0.012 (3)
C6A0.069 (3)0.069 (3)0.074 (3)0.015 (3)0.017 (3)0.007 (2)
C1B0.062 (3)0.082 (4)0.063 (3)0.009 (3)0.014 (2)0.001 (2)
C2B0.097 (4)0.096 (4)0.083 (4)0.004 (3)0.007 (3)0.002 (3)
C3B0.100 (5)0.117 (6)0.095 (5)0.017 (4)0.013 (4)0.027 (4)
C4B0.124 (6)0.082 (5)0.097 (5)0.024 (4)0.031 (4)0.020 (4)
F4B0.190 (4)0.116 (3)0.140 (3)0.045 (3)0.036 (3)0.047 (3)
C5B0.129 (6)0.077 (4)0.100 (5)0.010 (4)0.024 (4)0.004 (3)
C6B0.085 (4)0.088 (4)0.087 (4)0.010 (3)0.005 (3)0.003 (3)
C110.046 (2)0.044 (2)0.074 (3)0.0102 (19)0.006 (2)0.0063 (19)
C120.055 (3)0.075 (3)0.071 (3)0.007 (2)0.013 (2)0.003 (2)
C130.065 (3)0.067 (3)0.086 (4)0.010 (2)0.007 (3)0.000 (2)
C1C0.053 (3)0.055 (3)0.056 (3)0.000 (2)0.003 (2)0.0025 (19)
C2C0.074 (3)0.058 (3)0.100 (4)0.010 (2)0.016 (3)0.012 (3)
C3C0.085 (4)0.081 (4)0.098 (5)0.002 (3)0.009 (3)0.029 (3)
C4C0.101 (4)0.088 (4)0.078 (4)0.023 (4)0.013 (3)0.001 (3)
C5C0.097 (4)0.096 (4)0.084 (4)0.019 (3)0.015 (3)0.012 (3)
C6C0.080 (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)
Geometric parameters (Å, º) top
N1—C21.486 (5)N1'—C6'1.495 (5)
N1—C71.498 (5)N1'—C2'1.497 (5)
N1—C61.500 (5)N1'—C7'1.498 (5)
C2—C31.505 (6)C2'—C3'1.510 (5)
C3—N41.488 (5)C3'—N4'1.487 (5)
N4—C51.485 (4)N4'—C5'1.493 (5)
N4—C111.498 (5)N4'—C11'1.498 (5)
C5—C61.502 (6)C5'—C6'1.502 (5)
C7—C81.494 (6)C7'—C8'1.497 (6)
C8—O91.418 (5)C8'—O9'1.419 (5)
O9—C101.424 (5)O9'—C10'1.441 (5)
C10—C1B1.517 (7)C10'—C1B'1.509 (6)
C10—C1A1.523 (6)C10'—C1A'1.517 (6)
C1A—C6A1.365 (7)C1A'—C6A'1.363 (6)
C1A—C2A1.370 (7)C1A'—C2A'1.370 (7)
C2A—C3A1.397 (8)C2A'—C3A'1.391 (8)
C3A—C4A1.345 (9)C3A'—C4A'1.353 (8)
C4A—C5A1.344 (7)C4A'—C5A'1.332 (7)
C4A—F4A1.361 (6)C4A'—F4A'1.379 (6)
C5A—C6A1.374 (7)C5A'—C6A'1.384 (6)
C1B—C2B1.372 (7)C1B'—C2B'1.372 (7)
C1B—C6B1.389 (7)C1B'—C6B'1.373 (6)
C2B—C3B1.387 (8)C2B'—C3B'1.391 (8)
C3B—C4B1.343 (9)C3B'—C4B'1.344 (8)
C4B—C5B1.330 (8)C4B'—C5B'1.338 (8)
C4B—F4B1.353 (7)C4B'—F4B'1.348 (6)
C5B—C6B1.379 (8)C5B'—C6B'1.402 (7)
C11—C121.489 (6)C11'—C12'1.498 (6)
C12—C131.525 (6)C12'—C13'1.528 (6)
C13—C1C1.490 (6)C13'—C1C'1.482 (7)
C1C—C6C1.377 (6)C1C'—C6C'1.373 (7)
C1C—C2C1.378 (6)C1C'—C2C'1.385 (7)
C2C—C3C1.392 (7)C2C'—C3C'1.372 (7)
C3C—C4C1.360 (7)C3C'—C4C'1.354 (8)
C4C—C5C1.350 (7)C4C'—C5C'1.352 (8)
C5C—C6C1.364 (7)C5C'—C6C'1.369 (8)
C2—N1—C7113.1 (3)C6'—N1'—C2'110.2 (3)
C2—N1—C6110.0 (3)C6'—N1'—C7'110.6 (3)
C7—N1—C6110.3 (3)C2'—N1'—C7'113.0 (3)
N1—C2—C3111.5 (3)N1'—C2'—C3'111.6 (3)
N4—C3—C2112.2 (3)N4'—C3'—C2'111.8 (3)
C5—N4—C3109.2 (3)C3'—N4'—C5'109.7 (3)
C5—N4—C11112.3 (3)C3'—N4'—C11'112.4 (3)
C3—N4—C11112.6 (3)C5'—N4'—C11'112.2 (3)
N4—C5—C6111.3 (3)N4'—C5'—C6'110.9 (3)
N1—C6—C5111.4 (3)N1'—C6'—C5'111.8 (3)
C8—C7—N1114.8 (4)C8'—C7'—N1'114.7 (3)
O9—C8—C7111.4 (4)O9'—C8'—C7'111.0 (4)
C8—O9—C10112.2 (3)C8'—O9'—C10'112.1 (3)
O9—C10—C1B110.6 (4)O9'—C10'—C1B'111.0 (4)
O9—C10—C1A108.3 (4)O9'—C10'—C1A'107.9 (4)
C1B—C10—C1A112.7 (4)C1B'—C10'—C1A'112.8 (4)
C6A—C1A—C2A117.2 (5)C6A'—C1A'—C2A'117.7 (5)
C6A—C1A—C10121.1 (4)C6A'—C1A'—C10'123.1 (4)
C2A—C1A—C10121.6 (5)C2A'—C1A'—C10'119.0 (5)
C1A—C2A—C3A121.4 (6)C1A'—C2A'—C3A'121.3 (6)
C4A—C3A—C2A118.3 (6)C4A'—C3A'—C2A'118.2 (6)
C5A—C4A—C3A121.9 (6)C5A'—C4A'—C3A'122.4 (6)
C5A—C4A—F4A119.4 (6)C5A'—C4A'—F4A'119.2 (5)
C3A—C4A—F4A118.6 (6)C3A'—C4A'—F4A'118.4 (6)
C4A—C5A—C6A118.9 (6)C4A'—C5A'—C6A'118.8 (5)
C1A—C6A—C5A122.1 (5)C1A'—C6A'—C5A'121.6 (5)
C2B—C1B—C6B117.1 (5)C2B'—C1B'—C6B'119.0 (5)
C2B—C1B—C10121.8 (5)C2B'—C1B'—C10'120.6 (4)
C6B—C1B—C10121.0 (5)C6B'—C1B'—C10'120.4 (5)
C1B—C2B—C3B121.8 (6)C1B'—C2B'—C3B'120.0 (5)
C4B—C3B—C2B118.2 (6)C4B'—C3B'—C2B'119.8 (6)
C5B—C4B—C3B122.6 (6)C5B'—C4B'—C3B'121.9 (6)
C5B—C4B—F4B119.4 (7)C5B'—C4B'—F4B'119.4 (6)
C3B—C4B—F4B118.0 (7)C3B'—C4B'—F4B'118.6 (6)
C4B—C5B—C6B119.5 (6)C4B'—C5B'—C6B'119.2 (5)
C5B—C6B—C1B120.7 (5)C1B'—C6B'—C5B'120.2 (5)
C12—C11—N4114.4 (3)N4'—C11'—C12'114.1 (3)
C11—C12—C13110.4 (4)C11'—C12'—C13'110.3 (4)
C1C—C13—C12114.6 (4)C1C'—C13'—C12'115.2 (4)
C6C—C1C—C2C116.7 (4)C6C'—C1C'—C2C'116.2 (5)
C6C—C1C—C13121.3 (4)C6C'—C1C'—C13'121.3 (5)
C2C—C1C—C13121.9 (4)C2C'—C1C'—C13'122.4 (4)
C1C—C2C—C3C120.5 (5)C3C'—C2C'—C1C'121.5 (5)
C4C—C3C—C2C121.2 (5)C4C'—C3C'—C2C'120.5 (6)
C5C—C4C—C3C118.1 (6)C5C'—C4C'—C3C'119.3 (6)
C4C—C5C—C6C121.5 (5)C4C'—C5C'—C6C'120.5 (6)
C5C—C6C—C1C121.9 (5)C5C'—C6C'—C1C'122.0 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Cl40.912.143.034 (3)166
N4—H4A···Cl30.912.113.012 (3)174
N1—H1A···Cl20.912.133.027 (3)167
N4—H4A···Cl10.912.113.018 (3)173

Experimental details

Crystal data
Chemical formulaC28H34Cl2F2N2O
Mr523.47
Crystal system, space groupTriclinic, 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)
V3)2799.4 (2)
Z4
Radiation typeCu Kα
µ (mm1)2.38
Crystal size (mm)0.40 × 0.35 × 0.02
Data collection
DiffractometerBruker SMART 6000
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.386, 0.953
No. of measured, independent and
observed [I > 2σ(I)] reflections
9044, 9044, 6598
Rint0.000
(sin θ/λ)max1)0.598
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.065, 0.190, 0.97
No. of reflections9044
No. of parameters635
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.42, 0.26

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL (Bruker, 2001).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Cl40.912.143.034 (3)166.1
N4—H4A···Cl30.912.113.012 (3)173.6
N1'—H1'A···Cl20.912.133.027 (3)166.7
N4'—H4'A···Cl10.912.113.018 (3)173.1
 

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