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The crystal structure of the title mixed azine, C17H17ClN2O, contains four independent mol­ecules, A-D, and mol­ecule B is disordered. All four mol­ecules have an N-N gauche conformation, with C-N-N-C torsion angles of 136.5 (4), 137.0 (4), -134.7 (4) and -134.7 (4)°, respectively. The phenyl rings are also somewhat twisted with respect to the plane defined by Cipso and the imine bond. On average, the combined effect of these twists results in an angle of 64.7° between the best planes of the two phenyl rings. Arene-arene double T-contacts are the dominant intermolecular inter­action. The methoxy-substituted phenyl ring of one azine mol­ecule interacts to form a T-contact with the methoxy-substituted phenyl ring of an adjacent mol­ecule and, similarly, two chloro-substituted phenyl rings of neighboring mol­ecules interact to form another T-contact. The only exception is for mol­ecule B, for which the disorder leads to the formation of T-­contacts between methoxy- and chloro-substituted phenyl rings. The prevailing structural motif of T-contact formation between like-substituted arene rings results in a highly dipole-parallel-aligned crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270199011737/fr1211sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270199011737/fr1211Isup2.hkl
Contains datablock I

CCDC reference: 143276

Comment top

We have been investigating the stereochemistry (Glaser et al., 1993, 1995; Chen et al., 1995), electronics (Glaser et al., 1993; Chen et al., 1995; Glaser & Chen, 1998) and crystal packing (Glaser et al., 1993; Chen et al., 1995; Lewis et al., 1998, 1999) of symmetric and unsymmetric azines. An azine is the condensation product of two carbonyl molecules and hydrazine. The azines that we have studied have the general structure shown in Scheme 1 and they are called symmetric if X equals Y, and unsymmetric or mixed if X does not equal Y. All of the mixed azines that we have investigated [R = Me, X = OCH3, Y = Br, CN, or NO2; Glaser et al. (1995); R = Me, X = NH2, Y = F; Lewis et al., (1998)] have an N—N gauche conformation about the azine bridge. The N—N gauche conformation, in conjunction with a phenyl-ring twist, causes the two phenyl rings to be nearly orthogonal and this allows for the arene–arene double T-contact throughout the crystal structures of the previously studied mixed azines. A T-contact describes the edge-to-face interaction between two phenyl rings. Such arrangements are typically characterized by distances of 3.5–5.0 Å between the midpoints of the benzene rings (Hobza et al., 1994). A double T-contact occurs when the two phenyl rings of one spacer-connected biphenyl system interact with the two phenyl rings of another such molecule to form two intermolecular arene-arene T-contacts. Scheme 2 illustrates four types of double arene–arene contacts; I–III are all double T-contacts and IV is a double face-to-face contact. Type I has a planar spacer and the two phenyl rings in each molecule are coplanar. Types II and III contain a twisted spacer and the two phenyl rings in each molecule are twisted with respect to each other. Note that the double T-contacts II and III are structure isomers and differ only in the choice of the benzene edges used in the double T-contact. The double face-to-face contact, illustrated by IV, occurs when the two phenyl rings of each molecule interact in a face-to-face fashion. The double T-contacts present in all of the mixed azines that we have prepared to date have the conformations shown in (II) and (III), with inter-ring distances of 3.5–5.0 Å.

We are interested in mixed azines with the structure shown in Scheme 1 because of their promise as non-linear optical (NLO) materials. In order for a crystal to exhibit an NLO response, there are two necessary conditions. First, the crystals must be non-centrosymmetric or chiral, and this is a requirement for all types of polar effects of crystals (NLO activity, piezo- and pyroelectricity, ferroelectricity, ferroelasticity and many others). Non-centrosymmetry, in fact, occurs in approximately 20° of organic crystals (Sakamoto, 1997). The second condition, the central issue in the aggregation of crystals with macroscopic polarizations, is the parallel alignment of the dipole moments of the individual chromophores, and this is a challenge orders of magnitude greater than the simple quest for non-centrosymmetry. We have previously prepared 4-bromoacetophenone (4-methoxyphenylethylidene)hydrazone, (2) (X = OCH3, Y = Br, R = CH3; Chen et al., 1995). The crystal structure of (2) is highly anisotropic, with the long axes of all of the azine molecules pointing in the same direction, and moreover it has a high degree of dipole parallel-alignment, with all of the dipole moments also pointing in the same direction. In this report we discuss the crystal structure of 4-chloroacetophenone [1-(4-methoxyphenyl)ethylidene]hydrazone, (1) (X = OCH3, Y = Cl, R = CH3). As in the case of (2), azine (1) is an extremely anisotropic material, albeit with a somewhat lower degree of dipole parallel-alignment due to the disorder of molecules B.

Mixed azine (1) is the condensation product of a para-methoxyacetophenone molecule, a para-chloroacetophenone molecule and hydrazine. The bromine analog (2) was prepared previously and its crystal structure reported by Chen et al. (1995). The crystal structure of azine (2) is monoclinic with P21 symmetry [a = 7.766, b = 31.949 and c = 6.339 Å, β = 95.38° and Z = 4]. The similarity of the cell dimensions with those of azine (1) led us to assume that (1) and (2) were isostructural. Refinement of (1) in P21 gave a model in which one of the two independent molecules was disordered and the refinement converged to R = 13%. The merging R factor in the monoclinic setting, however, was 10% and an unconstrained refinement of the cell dimensions gave α and γ angles that deviated significantly from 90°. Refinement of the structure in the triclinic setting in space group P1 gave an R factor of 5%. In the triclinic structure there are four independent molecules in the unit cell (Fig. 1, molecules A—D) and the disorder is limited to only one molecule (B). Because of the deviation of unit-cell parameters from monoclinic and because the disorder is more localized, the crystal structure of (1) is better described in the triclinic setting.

The crystal structure of (1) is layered (Fig. 2), with molecules A and C always residing in one layer and molecules B and D in the other. Molecule B is disordered such that in 43% of the molecules the chloro group is pointing in the same direction as the chloro group of molecule D. For the other 57% of the molecules, the chloro group is pointing in the opposite direction. The layers in (1) are at an angle of approximately 35° with respect to each other. The conformation about the azine bridge in (1) (Fig. 1) is N—N gauche for all four independent molecules. The torsion angles C1—N1—N2—C9 are 136.5 (4), 137.0 (4), -134.7 (4) and -134.7 (4)° for molecules A—D, respectively. Our previous electronic investigations into the N—N gauche conformation of mixed azines showed that the azine bridge is essentially a conjugation stopper (Glaser & Chen, 1998). Crystallographic and ab initio studies showed that the bond distances and populations of one phenyl ring are virtually unaffected by the substitution pattern on the other phenyl ring. The N—N gauche conformation in (1) would suggest that the azine bridge is once again acting as a conjugation stopper. If this is true then we would expect little contribution from resonance form (1a) in the ground state structure of (1).

The importance of resonance form (1a) should be manifest through a structural comparison of mixed azine (1) with the symmetrical azines 4-methoxyacetophenone azine, (3) (R = CH3, X = Y = OMe; Glaser et al., 1995) and 4-chloroacetophenone azine, (4) (R = CH3, X = Y = Cl; Glaser et al., 1993). If there existed a substantial decrease in the C13—O1, C10—C9 and N2—N1 bond lengths and a significant increase in the C9N2 bond length in (1) with respect to (3), then this would suggest that conjugation played a role in the ground state of (1). Likewise, a decrease in the C2—C1 and N1—N2 bond lengths and an increase in the Cl1—C5 and C1N2 bond lengths in (1) with respect to (4) would also suggest that conjugation plays a significant role in the ground state of (1). We compared the four pertinent bond lengths for (1) and (3) [C13—O1, C9—N2, C9—C10 and N1—N2] and for (1) and (4) (Cl1—C5, C1—N1, C2—C1 and N1—N2) and in all cases the deviations are no greater than 0.02 Å. Moreover, the directions of these small changes are not consistent with contribution from resonance form (1a) to the ground state of (1). Thus, the azine bridge in (1) is operating as a conjugation stopper. The half of azine (1) with the methoxy-substituted phenyl ring is impervious to the substituent located on the phenyl ring in the other half, and the same statement can be made about the half of azine (1) with the chloro-substituted phenyl ring.

The crystal packing of mixed azine (1) (Fig. 2) is dominated by double T-contacts of the types described by II and III (Scheme 2). In the layer that contains molecules A and C, in which all of the molecules are ordered, the methoxy-substituted phenyl ring of azine molecule A is always involved in a T-contact with a methoxy-substituted ring of an adjacent azine molecule C. Likewise, the chloro-substituted phenyl ring of azine molecule A is always involved in a T-contact with a chloro-substituted phenyl ring of a neighboring azine molecule C. In this manner, each azine molecule A takes part in two type-II double T-contacts and one type-III double T-contact with neighboring azine C molecules. A similar motif is found for the layer containing molecules B and D, except that molecule B is disordered. Thus, in 43% of cases, the methoxy-substituted phenyl ring in azine molecule B is involved in a T-contact with the methoxy-substituted phenyl ring of an adjacent azine molecule D. In the other 57% of cases it is involved in a T-contact with the chloro-substituted phenyl ring of an adjacent azine molecule D. As was the case for the layer containing azine molecules A and C, each azine molecule in the layer containing molecules B and D takes part in two type-II double T-contacts and one type-III double T-contact.

The crystal structure of (1) has a high degree of dipole parallel-alignment. Ab initio molecular orbital calculations show that the vectors of the dipole moments of molecules A—D are all essentially along the long axis of each azine molecule. Furthermore, the direction of the N—N bond in each azine is also collinear with the long axis of the molecule and all of the N—N bonds are almost perfectly parallel. Thus, within the layer containing molecules A and C, the degree of dipole parallel-alignment is essentially complete. The disorder in molecule B detracts somewhat from the dipole parallel-alignment of the layer containing molecules B and D. After taking into account the disorder at molecule B, the degree of dipole parallel-alignment in the crystal structure of (1) is approximately 71.5% of the dipole parallel-alignment of (2). The crystal structure of (1), however, promises to be a better candidate for understanding the electronic factors involved in dipole parallel-alignment. Why is there disorder and why is the disorder so highly `organized' that it affects only molecules B? Molecule B exists in a crystal environment that is at the junction between dipole parallel-alignment and dipole antiparallel-alignment, and we are currently studying this phenomenon with ab initio molecular orbital theory.

The positional parameters of the disordered Cl and methoxy groups were not constrained or restrained during refinement, leading to less than ideal geometry for these moieties. In particular, the C—Cl bond distances are longer than those in the ordered molecules.

Experimental top

Diethylphosphite and hydrazine hydrate were reacted in a solution of tetrachloromethane, dichloromethane and potassium carbonate with a catalytic amount of triethylbenzylammonium chloride to give diethylphosphite hydrazine. The diethylphosphite hydrazine was then coupled with para-methoxyacetophenone in benzene to give diethylphosphine (4-methoxyphenylethylidene)hydrazone. The diethylphosphine (4-methoxyphenylethylidene)hydrazone was then coupled with para-chloroacetophenone to yield (1). Crystals of (1) were obtained by slow diffusion of hexane into a solution of (1) in chloroform.

Refinement top

H atoms were placed in calculated positions with C—H 0.95 Å (0.98 Å for methyl H) and Uiso = 1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SMART; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. ORTEPII (Johnson, 1976) drawing of molecules A—D of mixed azine (1) with 50% probability ellipsoids. H atoms are shown as spheres of arbitrary radii.
[Figure 2] Fig. 2. The crystal packing of mixed azine (1). The view is approximately down the a axis, with the origin at the lower right, b up and c to the left.
4-Chloroacetophenone [1-(4-methoxyphenyl)ethylidene]hydrazone top
Crystal data top
C17H17ClN2OZ = 4
Mr = 300.78F(000) = 632
Triclinic, P1Dx = 1.316 Mg m3
a = 6.3260 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 31.465 (2) ÅCell parameters from 7704 reflections
c = 7.6680 (4) Åθ = 1.3–27.0°
α = 90.264 (1)°µ = 0.25 mm1
β = 95.891 (1)°T = 173 K
γ = 90.154 (1)°Prism, yellow
V = 1518.21 (14) Å30.40 × 0.25 × 0.15 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
7038 reflections with I > 2σ(I)
ω scan b/P/bRint = 0.017
Absorption correction: empirical (using intensity measurements)
(SADABS; Blessing, 1995)
θmax = 27°
Tmin = 0.81, Tmax = 0.96h = 86
7704 measured reflectionsk = 4030
7704 independent reflectionsl = 89
Refinement top
Refinement on F2w = 1/[σ2(Fo2) + (0.0378P)2 + 1.7102P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.05(Δ/σ)max = 0.004
wR(F2) = 0.13Δρmax = 0.32 e Å3
S = 1.11Δρmin = 0.30 e Å3
7704 reflectionsAbsolute structure: Flack (1983)
760 parametersAbsolute structure parameter: 0.02 (7)
H-atom parameters constrained
Crystal data top
C17H17ClN2Oγ = 90.154 (1)°
Mr = 300.78V = 1518.21 (14) Å3
Triclinic, P1Z = 4
a = 6.3260 (3) ÅMo Kα radiation
b = 31.465 (2) ŵ = 0.25 mm1
c = 7.6680 (4) ÅT = 173 K
α = 90.264 (1)°0.40 × 0.25 × 0.15 mm
β = 95.891 (1)°
Data collection top
Siemens SMART CCD area-detector
diffractometer
7704 independent reflections
Absorption correction: empirical (using intensity measurements)
(SADABS; Blessing, 1995)
7038 reflections with I > 2σ(I)
Tmin = 0.81, Tmax = 0.96Rint = 0.017
7704 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05H-atom parameters constrained
wR(F2) = 0.13Δρmax = 0.32 e Å3
S = 1.11Δρmin = 0.30 e Å3
7704 reflectionsAbsolute structure: Flack (1983)
760 parametersAbsolute structure parameter: 0.02 (7)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl1A0.5483 (3)0.03558 (5)0.59592 (19)0.0566 (4)
O1A0.0149 (6)0.45699 (11)1.1130 (4)0.0424 (9)
N1A0.2856 (6)0.23509 (11)0.7822 (5)0.0270 (8)
N2A0.1932 (6)0.27336 (12)0.8265 (5)0.0277 (8)
C1A0.1637 (7)0.20195 (14)0.7896 (5)0.0245 (9)
C2A0.2553 (7)0.16070 (14)0.7385 (6)0.0263 (9)
C3A0.1627 (8)0.12171 (15)0.7798 (6)0.0364 (11)
H3A0.03680.12170.83750.044*
C4A0.2515 (9)0.08350 (16)0.7377 (7)0.0406 (12)
H4A0.18780.05740.76670.049*
C5A0.4338 (9)0.08347 (15)0.6533 (6)0.0359 (11)
C6A0.5279 (8)0.12096 (15)0.6095 (6)0.0309 (10)
H6A0.65360.12040.55150.037*
C7A0.4383 (7)0.15952 (14)0.6505 (6)0.0277 (9)
H7A0.50190.18530.61840.033*
C8A0.0506 (8)0.20329 (16)0.8549 (7)0.0386 (11)
H8A30.14840.18480.78190.046*
H8A20.10410.23250.84910.046*
H8A10.03980.19350.97660.046*
C9A0.3161 (6)0.29812 (14)0.9279 (5)0.0237 (9)
C10A0.2268 (7)0.33970 (13)0.9732 (5)0.0230 (8)
C11A0.3352 (7)0.36629 (14)1.1011 (5)0.0254 (9)
H11A0.46770.35751.15890.030*
C12A0.2511 (8)0.40499 (15)1.1434 (6)0.0312 (10)
H12A0.32690.42261.22940.037*
C13A0.0568 (7)0.41841 (14)1.0614 (6)0.0261 (9)
C14A0.0528 (7)0.39230 (15)0.9355 (6)0.0308 (10)
H14A0.18580.40120.87880.037*
C15A0.0308 (7)0.35357 (15)0.8928 (6)0.0268 (9)
H15A0.04620.33600.80710.032*
C16A0.5382 (7)0.28680 (15)1.0019 (6)0.0326 (10)
H16C0.63310.31100.98930.039*
H16B0.58730.26220.93840.039*
H16A0.53880.27981.12640.039*
C17A0.2137 (9)0.47129 (18)1.0318 (7)0.0534 (16)
H17C0.32780.45361.06980.064*
H17B0.21470.46930.90420.064*
H17A0.23570.50091.06550.064*
Cl1B0.9858 (6)0.97327 (8)0.5058 (4)0.0513 (11)0.575 (7)
O1B0.4226 (10)0.54570 (17)0.9444 (8)0.0335 (15)*0.575 (7)
N1B0.7216 (6)0.77698 (13)0.7598 (5)0.0327 (9)
N2B0.6283 (6)0.73830 (12)0.8017 (5)0.0303 (8)
C1B0.6008 (7)0.80158 (15)0.6610 (6)0.0297 (10)
C2B0.6892 (7)0.84334 (15)0.6181 (6)0.0297 (10)
C3B0.5800 (8)0.87041 (16)0.4950 (6)0.0363 (11)
H3B0.44650.86170.43780.044*
C4B0.6619 (9)0.90906 (17)0.4557 (7)0.0420 (13)
H4B0.58530.92680.37170.050*
C5B0.8556 (8)0.92243 (15)0.5377 (7)0.0375 (12)
C6B0.9703 (9)0.89646 (16)0.6608 (7)0.0416 (12)
H6B1.10380.90550.71710.050*
C7B0.8855 (8)0.85694 (16)0.6999 (7)0.0346 (11)
H7B0.96250.83910.78330.042*
C8B0.3812 (8)0.78975 (16)0.5825 (7)0.0387 (11)
H8B30.28470.81360.59530.046*
H8B20.33160.76490.64320.046*
H8B10.38410.78310.45780.046*
C9B0.7500 (7)0.70532 (14)0.7940 (5)0.0271 (9)
C10B0.6602 (7)0.66388 (14)0.8423 (5)0.0267 (9)
C11B0.7503 (8)0.62573 (15)0.7930 (6)0.0328 (11)
H11B0.87430.62630.73290.039*
C12B0.6609 (8)0.58712 (15)0.8307 (6)0.0363 (12)
H12B0.72470.56150.79700.044*
C13B0.4782 (8)0.58552 (14)0.9176 (6)0.0311 (10)
C14B0.3894 (8)0.62323 (14)0.9693 (6)0.0327 (10)
H14B0.26670.62251.03100.039*
C15B0.4782 (8)0.66184 (14)0.9317 (6)0.0321 (10)
H15B0.41490.68740.96710.039*
C16B0.9657 (8)0.70702 (17)0.7308 (8)0.0428 (12)
H16F1.04850.68240.77520.051*
H16E1.03830.73320.77340.051*
H16D0.95150.70660.60230.051*
C17B0.2360 (14)0.5425 (3)1.0342 (12)0.039 (2)*0.575 (7)
Cl1C0.1034 (2)0.00180 (4)0.06669 (18)0.0490 (4)
O1C0.4585 (5)0.42402 (9)0.5654 (4)0.0284 (7)
N1C0.1536 (6)0.19253 (11)0.3647 (5)0.0274 (8)
N2C0.2441 (6)0.23104 (11)0.4103 (5)0.0277 (8)
C1C0.2740 (7)0.16819 (13)0.2629 (5)0.0240 (9)
C2C0.1846 (7)0.12643 (13)0.2164 (6)0.0248 (9)
C3C0.2977 (8)0.09919 (15)0.0976 (7)0.0365 (11)
H3C0.43540.10690.04660.044*
C4C0.2094 (8)0.06039 (15)0.0529 (7)0.0402 (12)
H4C0.28740.04170.02740.048*
C5C0.0092 (8)0.04947 (14)0.1257 (6)0.0357 (11)
C6C0.1045 (8)0.07580 (16)0.2442 (6)0.0353 (11)
H6C0.24190.06780.29500.042*
C7C0.0166 (8)0.11406 (15)0.2886 (6)0.0319 (10)
H7C0.09540.13230.37030.038*
C8C0.4930 (7)0.17986 (15)0.1837 (7)0.0351 (11)
H8C30.48920.18640.05920.042*
H8C20.54260.20480.24460.042*
H8C10.59020.15600.19560.042*
C9C0.1227 (7)0.26371 (13)0.4003 (5)0.0231 (9)
C10C0.2113 (6)0.30536 (13)0.4492 (5)0.0214 (8)
C11C0.1216 (7)0.34374 (13)0.3972 (5)0.0246 (9)
H11C0.00050.34290.33360.030*
C12C0.2073 (7)0.38264 (13)0.4376 (6)0.0260 (9)
H12C0.14500.40820.40160.031*
C13C0.3853 (6)0.38415 (13)0.5313 (5)0.0216 (8)
C14C0.4771 (6)0.34658 (13)0.5824 (5)0.0236 (9)
H14C0.59870.34740.64540.028*
C15C0.3900 (6)0.30789 (14)0.5408 (5)0.0246 (9)
H15C0.45410.28240.57580.029*
C16C0.0923 (7)0.26221 (15)0.3365 (7)0.0354 (11)
H16I0.08190.27080.21330.043*
H16H0.14790.23320.34760.043*
H16G0.18830.28160.40690.043*
C17C0.6431 (8)0.42766 (15)0.6533 (7)0.0365 (11)
H17F0.61920.41390.76800.044*
H17E0.76260.41380.58360.044*
H17D0.67570.45780.66930.044*
Cl1D0.8064 (2)0.50219 (4)0.50457 (16)0.0472 (3)
O1D1.3775 (5)0.92542 (10)0.0350 (5)0.0379 (8)
N1D1.0625 (6)0.69414 (12)0.2186 (5)0.0285 (8)
N2D1.1529 (6)0.73258 (12)0.1756 (5)0.0300 (8)
C1D1.1849 (7)0.66975 (13)0.3210 (5)0.0242 (9)
C2D1.0918 (7)0.62773 (13)0.3634 (6)0.0238 (9)
C3D1.2045 (8)0.60038 (15)0.4832 (6)0.0333 (11)
H3D1.34110.60850.53620.040*
C4D1.1183 (8)0.56150 (15)0.5254 (7)0.0346 (11)
H4D1.19580.54300.60590.042*
C5D0.9194 (8)0.55004 (14)0.4491 (6)0.0322 (11)
C6D0.8082 (8)0.57656 (15)0.3306 (6)0.0309 (10)
H6D0.67210.56820.27750.037*
C7D0.8921 (7)0.61500 (14)0.2882 (6)0.0289 (10)
H7D0.81310.63300.20680.035*
C8D1.4021 (7)0.68109 (16)0.3979 (7)0.0343 (11)
H8D31.39970.68800.52240.041*
H8D21.45300.70570.33650.041*
H8D11.49730.65700.38580.041*
C9D1.0328 (7)0.76529 (14)0.1862 (6)0.0251 (9)
C10D1.1206 (7)0.80666 (14)0.1391 (6)0.0257 (9)
C11D1.0362 (8)0.84507 (15)0.1939 (6)0.0312 (10)
H11D0.91550.84440.25810.037*
C12D1.1233 (8)0.88368 (15)0.1575 (6)0.0330 (11)
H12D1.06230.90920.19580.040*
C13D1.3015 (7)0.88540 (14)0.0640 (6)0.0287 (10)
C14D1.3931 (7)0.84795 (14)0.0112 (6)0.0281 (9)
H14D1.51620.84880.05010.034*
C15D1.3021 (7)0.80937 (14)0.0493 (6)0.0252 (9)
H15D1.36530.78390.01330.030*
C16D0.8165 (7)0.76361 (15)0.2503 (7)0.0353 (11)
H16L0.83120.76390.37880.042*
H16K0.74340.73750.20750.042*
H16J0.73370.78830.20650.042*
C17D1.5652 (9)0.92907 (17)0.0536 (9)0.0490 (14)
H17I1.54170.91500.16820.059*
H17H1.68440.91550.01660.059*
H17G1.59790.95920.06970.059*
Cl1E0.3339 (6)0.53723 (11)0.9759 (4)0.0422 (12)*0.425 (7)
O1E0.9066 (16)0.9593 (3)0.4747 (12)0.045 (3)*0.425 (7)
C17E1.115 (2)0.9733 (5)0.553 (2)0.055 (4)*0.425 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.0847 (11)0.0313 (7)0.0549 (9)0.0184 (7)0.0122 (7)0.0019 (6)
O1A0.056 (2)0.041 (2)0.0287 (18)0.0090 (16)0.0014 (15)0.0087 (15)
N1A0.030 (2)0.0226 (19)0.029 (2)0.0013 (15)0.0069 (15)0.0019 (14)
N2A0.029 (2)0.0252 (19)0.0292 (19)0.0010 (15)0.0068 (16)0.0011 (15)
C1A0.026 (2)0.028 (2)0.019 (2)0.0009 (17)0.0011 (17)0.0008 (16)
C2A0.029 (2)0.026 (2)0.023 (2)0.0023 (17)0.0000 (17)0.0012 (17)
C3A0.041 (3)0.033 (3)0.037 (3)0.002 (2)0.013 (2)0.005 (2)
C4A0.055 (3)0.030 (3)0.039 (3)0.007 (2)0.009 (2)0.004 (2)
C5A0.056 (3)0.023 (2)0.028 (2)0.009 (2)0.000 (2)0.0045 (18)
C6A0.035 (3)0.031 (2)0.027 (2)0.0015 (19)0.0042 (19)0.0023 (18)
C7A0.032 (2)0.028 (2)0.023 (2)0.0032 (18)0.0021 (18)0.0005 (17)
C8A0.031 (3)0.033 (3)0.054 (3)0.0043 (19)0.013 (2)0.005 (2)
C9A0.022 (2)0.030 (2)0.020 (2)0.0005 (16)0.0048 (16)0.0060 (16)
C10A0.029 (2)0.025 (2)0.0160 (19)0.0019 (16)0.0055 (16)0.0026 (15)
C11A0.027 (2)0.031 (2)0.0176 (19)0.0010 (17)0.0031 (16)0.0005 (16)
C12A0.040 (3)0.035 (3)0.018 (2)0.001 (2)0.0005 (18)0.0027 (17)
C13A0.031 (2)0.023 (2)0.025 (2)0.0015 (17)0.0032 (18)0.0001 (16)
C14A0.032 (2)0.030 (2)0.030 (2)0.0071 (19)0.0048 (19)0.0026 (18)
C15A0.023 (2)0.030 (2)0.028 (2)0.0020 (17)0.0027 (17)0.0014 (17)
C16A0.030 (2)0.032 (2)0.034 (2)0.0038 (19)0.002 (2)0.0038 (19)
C17A0.065 (4)0.047 (3)0.047 (3)0.030 (3)0.002 (3)0.008 (3)
Cl1B0.076 (3)0.0295 (14)0.0515 (16)0.0007 (14)0.0230 (16)0.0120 (11)
N1B0.035 (2)0.030 (2)0.035 (2)0.0048 (16)0.0128 (17)0.0069 (16)
N2B0.033 (2)0.0268 (19)0.032 (2)0.0017 (16)0.0058 (16)0.0042 (15)
C1B0.034 (2)0.033 (2)0.024 (2)0.0082 (19)0.0106 (18)0.0003 (18)
C2B0.031 (2)0.035 (2)0.024 (2)0.0096 (19)0.0079 (18)0.0019 (18)
C3B0.040 (3)0.040 (3)0.029 (2)0.007 (2)0.003 (2)0.006 (2)
C4B0.055 (3)0.041 (3)0.032 (3)0.017 (2)0.013 (2)0.013 (2)
C5B0.050 (3)0.029 (2)0.038 (3)0.008 (2)0.024 (2)0.010 (2)
C6B0.045 (3)0.035 (3)0.049 (3)0.005 (2)0.021 (2)0.008 (2)
C7B0.035 (3)0.031 (3)0.041 (3)0.003 (2)0.015 (2)0.010 (2)
C8B0.040 (3)0.036 (3)0.039 (3)0.004 (2)0.001 (2)0.003 (2)
C9B0.031 (2)0.031 (2)0.019 (2)0.0054 (18)0.0041 (17)0.0022 (17)
C10B0.031 (2)0.029 (2)0.020 (2)0.0061 (18)0.0033 (17)0.0013 (17)
C11B0.039 (3)0.035 (3)0.025 (2)0.012 (2)0.0044 (19)0.0007 (18)
C12B0.046 (3)0.029 (3)0.033 (3)0.013 (2)0.003 (2)0.0052 (19)
C13B0.048 (3)0.020 (2)0.024 (2)0.0022 (19)0.002 (2)0.0004 (16)
C14B0.043 (3)0.028 (2)0.029 (2)0.004 (2)0.010 (2)0.0034 (18)
C15B0.044 (3)0.023 (2)0.030 (2)0.0082 (19)0.010 (2)0.0040 (18)
C16B0.039 (3)0.041 (3)0.050 (3)0.006 (2)0.015 (2)0.009 (2)
Cl1C0.0747 (10)0.0220 (6)0.0539 (8)0.0117 (6)0.0231 (7)0.0008 (5)
O1C0.0302 (17)0.0221 (15)0.0332 (17)0.0016 (12)0.0044 (13)0.0011 (12)
N1C0.030 (2)0.0225 (19)0.030 (2)0.0034 (15)0.0058 (16)0.0004 (15)
N2C0.031 (2)0.0204 (18)0.033 (2)0.0030 (15)0.0077 (16)0.0011 (15)
C1C0.031 (2)0.021 (2)0.021 (2)0.0006 (16)0.0071 (17)0.0009 (16)
C2C0.027 (2)0.022 (2)0.026 (2)0.0016 (16)0.0060 (17)0.0025 (16)
C3C0.038 (3)0.028 (3)0.043 (3)0.002 (2)0.002 (2)0.003 (2)
C4C0.045 (3)0.026 (3)0.049 (3)0.003 (2)0.002 (2)0.010 (2)
C5C0.056 (3)0.019 (2)0.035 (3)0.009 (2)0.017 (2)0.0005 (18)
C6C0.039 (3)0.034 (3)0.033 (3)0.011 (2)0.007 (2)0.000 (2)
C7C0.041 (3)0.027 (2)0.028 (2)0.0057 (19)0.001 (2)0.0059 (18)
C8C0.032 (3)0.030 (2)0.043 (3)0.0050 (19)0.000 (2)0.002 (2)
C9C0.024 (2)0.024 (2)0.020 (2)0.0002 (16)0.0016 (16)0.0021 (16)
C10C0.023 (2)0.024 (2)0.0172 (19)0.0011 (15)0.0013 (15)0.0030 (15)
C11C0.024 (2)0.027 (2)0.023 (2)0.0051 (16)0.0049 (17)0.0001 (16)
C12C0.029 (2)0.023 (2)0.027 (2)0.0058 (16)0.0054 (18)0.0017 (17)
C13C0.020 (2)0.024 (2)0.0186 (19)0.0041 (15)0.0056 (16)0.0004 (15)
C14C0.021 (2)0.028 (2)0.022 (2)0.0015 (16)0.0051 (16)0.0009 (16)
C15C0.025 (2)0.025 (2)0.024 (2)0.0056 (16)0.0029 (17)0.0031 (16)
C16C0.031 (3)0.029 (2)0.048 (3)0.0035 (19)0.012 (2)0.001 (2)
C17C0.039 (3)0.027 (2)0.045 (3)0.0044 (19)0.014 (2)0.004 (2)
Cl1D0.0806 (10)0.0235 (6)0.0402 (7)0.0120 (6)0.0196 (6)0.0012 (5)
O1D0.0399 (19)0.0214 (16)0.056 (2)0.0018 (13)0.0207 (16)0.0004 (14)
N1D0.032 (2)0.0230 (19)0.031 (2)0.0005 (15)0.0069 (16)0.0037 (15)
N2D0.037 (2)0.0242 (19)0.030 (2)0.0014 (16)0.0076 (16)0.0050 (15)
C1D0.030 (2)0.019 (2)0.025 (2)0.0001 (16)0.0099 (17)0.0033 (16)
C2D0.031 (2)0.0171 (19)0.024 (2)0.0003 (16)0.0062 (17)0.0020 (15)
C3D0.039 (3)0.028 (2)0.033 (3)0.002 (2)0.003 (2)0.0057 (19)
C4D0.046 (3)0.024 (2)0.033 (3)0.001 (2)0.001 (2)0.0046 (19)
C5D0.053 (3)0.014 (2)0.031 (2)0.0064 (19)0.014 (2)0.0008 (17)
C6D0.037 (3)0.032 (2)0.024 (2)0.0069 (19)0.0029 (19)0.0048 (18)
C7D0.039 (3)0.026 (2)0.021 (2)0.0004 (18)0.0005 (18)0.0002 (17)
C8D0.035 (3)0.030 (3)0.039 (3)0.0007 (19)0.009 (2)0.003 (2)
C9D0.030 (2)0.025 (2)0.021 (2)0.0004 (17)0.0037 (16)0.0003 (16)
C10D0.029 (2)0.023 (2)0.025 (2)0.0025 (17)0.0037 (17)0.0014 (16)
C11D0.038 (3)0.027 (2)0.031 (2)0.0068 (19)0.017 (2)0.0027 (18)
C12D0.039 (3)0.024 (2)0.039 (3)0.0077 (19)0.016 (2)0.0031 (19)
C13D0.035 (2)0.021 (2)0.031 (2)0.0052 (18)0.0074 (19)0.0038 (17)
C14D0.031 (2)0.022 (2)0.033 (2)0.0009 (17)0.0128 (19)0.0007 (17)
C15D0.028 (2)0.022 (2)0.026 (2)0.0042 (17)0.0043 (17)0.0009 (16)
C16D0.030 (2)0.030 (3)0.047 (3)0.0021 (19)0.012 (2)0.007 (2)
C17D0.047 (3)0.031 (3)0.075 (4)0.003 (2)0.028 (3)0.011 (3)
Geometric parameters (Å, º) top
Cl1A—C5A1.748 (5)C17B—Cl1E0.818 (9)
O1A—C13A1.368 (5)Cl1C—C5C1.740 (4)
O1A—C17A1.420 (6)O1C—C13C1.372 (5)
N1A—C1A1.300 (6)O1C—C17C1.412 (6)
N1A—N2A1.396 (5)N1C—C1C1.283 (5)
N2A—C9A1.297 (6)N1C—N2C1.400 (5)
C1A—C2A1.490 (6)N2C—C9C1.289 (6)
C1A—C8A1.493 (6)C1C—C2C1.488 (5)
C2A—C7A1.399 (6)C1C—C8C1.502 (6)
C2A—C3A1.409 (7)C2C—C3C1.390 (6)
C3A—C4A1.379 (7)C2C—C7C1.392 (6)
C3A—H3A0.9500C3C—C4C1.400 (6)
C4A—C5A1.379 (7)C3C—H3C0.9500
C4A—H4A0.9500C4C—C5C1.376 (7)
C5A—C6A1.378 (7)C4C—H4C0.9500
C6A—C7A1.389 (6)C5C—C6C1.373 (7)
C6A—H6A0.9500C6C—C7C1.383 (6)
C7A—H7A0.9500C6C—H6C0.9500
C8A—H8A30.9800C7C—H7C0.9500
C8A—H8A20.9800C8C—H8C30.9800
C8A—H8A10.9800C8C—H8C20.9800
C9A—C10A1.481 (6)C8C—H8C10.9800
C9A—C16A1.505 (6)C9C—C10C1.488 (5)
C10A—C15A1.399 (6)C9C—C16C1.493 (6)
C10A—C11A1.408 (6)C10C—C15C1.394 (6)
C11A—C12A1.381 (6)C10C—C11C1.409 (6)
C11A—H11A0.9500C11C—C12C1.387 (6)
C12A—C13A1.390 (6)C11C—H11C0.9500
C12A—H12A0.9500C12C—C13C1.397 (6)
C13A—C14A1.393 (6)C12C—H12C0.9500
C14A—C15A1.381 (6)C13C—C14C1.391 (6)
C14A—H14A0.9500C14C—C15C1.387 (6)
C15A—H15A0.9500C14C—H14C0.9500
C16A—H16C0.9800C15C—H15C0.9500
C16A—H16B0.9800C16C—H16I0.9800
C16A—H16A0.9800C16C—H16H0.9800
C17A—H17C0.9800C16C—H16G0.9800
C17A—H17B0.9800C17C—H17F0.9800
C17A—H17A0.9800C17C—H17E0.9800
Cl1B—O1E0.689 (9)C17C—H17D0.9800
Cl1B—C17E0.861 (14)Cl1D—C5D1.738 (5)
Cl1B—C5B1.826 (6)O1D—C13D1.374 (5)
O1B—Cl1E0.687 (6)O1D—C17D1.432 (6)
O1B—C13B1.323 (7)N1D—C1D1.299 (5)
O1B—C17B1.430 (11)N1D—N2D1.392 (5)
N1B—C1B1.284 (6)N2D—C9D1.288 (5)
N1B—N2B1.404 (5)C1D—C8D1.481 (7)
N2B—C9B1.299 (5)C1D—C2D1.497 (6)
C1B—C2B1.478 (7)C2D—C7D1.391 (6)
C1B—C8B1.501 (7)C2D—C3D1.403 (6)
C2B—C7B1.398 (7)C3D—C4D1.391 (7)
C2B—C3B1.404 (6)C3D—H3D0.9500
C3B—C4B1.368 (7)C4D—C5D1.378 (7)
C3B—H3B0.9500C4D—H4D0.9500
C4B—C5B1.382 (8)C5D—C6D1.377 (7)
C4B—H4B0.9500C6D—C7D1.373 (6)
C5B—O1E1.311 (9)C6D—H6D0.9500
C5B—C6B1.398 (7)C7D—H7D0.9500
C6B—C7B1.399 (7)C8D—H8D30.9800
C6B—H6B0.9500C8D—H8D20.9800
C7B—H7B0.9500C8D—H8D10.9800
C8B—H8B30.9800C9D—C10D1.475 (6)
C8B—H8B20.9800C9D—C16D1.502 (6)
C8B—H8B10.9800C10D—C15D1.401 (6)
C9B—C10B1.485 (6)C10D—C11D1.403 (6)
C9B—C16B1.495 (7)C11D—C12D1.374 (7)
C10B—C11B1.398 (6)C11D—H11D0.9500
C10B—C15B1.401 (7)C12D—C13D1.398 (7)
C11B—C12B1.383 (7)C12D—H12D0.9500
C11B—H11B0.9500C13D—C14D1.391 (6)
C12B—C13B1.393 (7)C14D—C15D1.387 (6)
C12B—H12B0.9500C14D—H14D0.9500
C13B—C14B1.388 (6)C15D—H15D0.9500
C13B—Cl1E1.850 (6)C16D—H16L0.9800
C14B—C15B1.381 (7)C16D—H16K0.9800
C14B—H14B0.9500C16D—H16J0.9800
C15B—H15B0.9500C17D—H17I0.9800
C16B—H16F0.9800C17D—H17H0.9800
C16B—H16E0.9800C17D—H17G0.9800
C16B—H16D0.9800O1E—C17E1.459 (14)
C13A—O1A—C17A117.6 (4)C1C—N1C—N2C115.6 (3)
C1A—N1A—N2A114.5 (4)C9C—N2C—N1C114.4 (4)
C9A—N2A—N1A114.8 (3)N1C—C1C—C2C116.9 (4)
N1A—C1A—C2A115.9 (4)N1C—C1C—C8C124.3 (4)
N1A—C1A—C8A123.7 (4)C2C—C1C—C8C118.7 (4)
C2A—C1A—C8A120.3 (4)C3C—C2C—C7C118.3 (4)
C7A—C2A—C3A118.0 (4)C3C—C2C—C1C121.0 (4)
C7A—C2A—C1A120.9 (4)C7C—C2C—C1C120.7 (4)
C3A—C2A—C1A121.1 (4)C2C—C3C—C4C120.2 (4)
C4A—C3A—C2A121.2 (5)C2C—C3C—H3C119.9
C4A—C3A—H3A119.4C4C—C3C—H3C119.9
C2A—C3A—H3A119.4C5C—C4C—C3C119.8 (4)
C3A—C4A—C5A119.4 (5)C5C—C4C—H4C120.1
C3A—C4A—H4A120.3C3C—C4C—H4C120.1
C5A—C4A—H4A120.3C6C—C5C—C4C120.9 (4)
C6A—C5A—C4A121.1 (4)C6C—C5C—Cl1C119.2 (4)
C6A—C5A—Cl1A118.4 (4)C4C—C5C—Cl1C119.9 (4)
C4A—C5A—Cl1A120.5 (4)C5C—C6C—C7C119.2 (4)
C5A—C6A—C7A119.7 (4)C5C—C6C—H6C120.4
C5A—C6A—H6A120.1C7C—C6C—H6C120.4
C7A—C6A—H6A120.1C6C—C7C—C2C121.6 (4)
C6A—C7A—C2A120.6 (4)C6C—C7C—H7C119.2
C6A—C7A—H7A119.7C2C—C7C—H7C119.2
C2A—C7A—H7A119.7C1C—C8C—H8C3109.5
C1A—C8A—H8A3109.5C1C—C8C—H8C2109.5
C1A—C8A—H8A2109.5H8C3—C8C—H8C2109.5
H8A3—C8A—H8A2109.5C1C—C8C—H8C1109.5
C1A—C8A—H8A1109.5H8C3—C8C—H8C1109.5
H8A3—C8A—H8A1109.5H8C2—C8C—H8C1109.5
H8A2—C8A—H8A1109.5N2C—C9C—C10C116.4 (4)
N2A—C9A—C10A116.6 (4)N2C—C9C—C16C124.2 (4)
N2A—C9A—C16A124.2 (4)C10C—C9C—C16C119.4 (4)
C10A—C9A—C16A119.2 (4)C15C—C10C—C11C117.7 (4)
C15A—C10A—C11A117.8 (4)C15C—C10C—C9C121.6 (4)
C15A—C10A—C9A121.2 (4)C11C—C10C—C9C120.7 (4)
C11A—C10A—C9A121.0 (4)C12C—C11C—C10C121.0 (4)
C12A—C11A—C10A120.8 (4)C12C—C11C—H11C119.5
C12A—C11A—H11A119.6C10C—C11C—H11C119.5
C10A—C11A—H11A119.6C11C—C12C—C13C119.9 (4)
C11A—C12A—C13A120.6 (4)C11C—C12C—H12C120.0
C11A—C12A—H12A119.7C13C—C12C—H12C120.0
C13A—C12A—H12A119.7O1C—C13C—C14C124.4 (4)
O1A—C13A—C12A116.5 (4)O1C—C13C—C12C115.8 (4)
O1A—C13A—C14A124.3 (4)C14C—C13C—C12C119.9 (4)
C12A—C13A—C14A119.2 (4)C15C—C14C—C13C119.6 (4)
C15A—C14A—C13A120.4 (4)C15C—C14C—H14C120.2
C15A—C14A—H14A119.8C13C—C14C—H14C120.2
C13A—C14A—H14A119.8C14C—C15C—C10C121.9 (4)
C14A—C15A—C10A121.2 (4)C14C—C15C—H15C119.1
C14A—C15A—H15A119.4C10C—C15C—H15C119.1
C10A—C15A—H15A119.4C9C—C16C—H16I109.5
C9A—C16A—H16C109.5C9C—C16C—H16H109.5
C9A—C16A—H16B109.5H16I—C16C—H16H109.5
H16C—C16A—H16B109.5C9C—C16C—H16G109.5
C9A—C16A—H16A109.5H16I—C16C—H16G109.5
H16C—C16A—H16A109.5H16H—C16C—H16G109.5
H16B—C16A—H16A109.5O1C—C17C—H17F109.5
O1A—C17A—H17C109.5O1C—C17C—H17E109.5
O1A—C17A—H17B109.5H17F—C17C—H17E109.5
H17C—C17A—H17B109.5O1C—C17C—H17D109.5
O1A—C17A—H17A109.5H17F—C17C—H17D109.5
H17C—C17A—H17A109.5H17E—C17C—H17D109.5
H17B—C17A—H17A109.5C13D—O1D—C17D118.1 (4)
O1E—Cl1B—C17E140.5 (13)C1D—N1D—N2D115.2 (4)
O1E—Cl1B—C5B33.8 (7)C9D—N2D—N1D114.9 (4)
C17E—Cl1B—C5B111.3 (10)N1D—C1D—C8D124.8 (4)
Cl1E—O1B—C13B131.4 (8)N1D—C1D—C2D115.7 (4)
Cl1E—O1B—C17B19.8 (6)C8D—C1D—C2D119.5 (4)
C13B—O1B—C17B112.8 (6)C7D—C2D—C3D118.4 (4)
C1B—N1B—N2B115.0 (4)C7D—C2D—C1D121.4 (4)
C9B—N2B—N1B114.7 (4)C3D—C2D—C1D120.2 (4)
N1B—C1B—C2B117.1 (4)C4D—C3D—C2D120.7 (5)
N1B—C1B—C8B124.0 (5)C4D—C3D—H3D119.6
C2B—C1B—C8B118.9 (4)C2D—C3D—H3D119.6
C7B—C2B—C3B118.1 (5)C5D—C4D—C3D119.4 (4)
C7B—C2B—C1B120.5 (4)C5D—C4D—H4D120.3
C3B—C2B—C1B121.5 (4)C3D—C4D—H4D120.3
C4B—C3B—C2B121.4 (5)C6D—C5D—C4D120.3 (4)
C4B—C3B—H3B119.3C6D—C5D—Cl1D119.7 (4)
C2B—C3B—H3B119.3C4D—C5D—Cl1D120.0 (4)
C3B—C4B—C5B120.3 (4)C7D—C6D—C5D120.7 (4)
C3B—C4B—H4B119.9C7D—C6D—H6D119.7
C5B—C4B—H4B119.9C5D—C6D—H6D119.7
O1E—C5B—C4B109.7 (6)C6D—C7D—C2D120.6 (4)
O1E—C5B—C6B129.8 (6)C6D—C7D—H7D119.7
C4B—C5B—C6B120.3 (5)C2D—C7D—H7D119.7
O1E—C5B—Cl1B17.0 (4)C1D—C8D—H8D3109.5
C4B—C5B—Cl1B126.3 (4)C1D—C8D—H8D2109.5
C6B—C5B—Cl1B113.3 (4)H8D3—C8D—H8D2109.5
C5B—C6B—C7B119.0 (5)C1D—C8D—H8D1109.5
C5B—C6B—H6B120.5H8D3—C8D—H8D1109.5
C7B—C6B—H6B120.5H8D2—C8D—H8D1109.5
C2B—C7B—C6B121.0 (5)N2D—C9D—C10D116.9 (4)
C2B—C7B—H7B119.5N2D—C9D—C16D123.8 (4)
C6B—C7B—H7B119.5C10D—C9D—C16D119.3 (4)
C1B—C8B—H8B3109.5C15D—C10D—C11D116.8 (4)
C1B—C8B—H8B2109.5C15D—C10D—C9D121.5 (4)
H8B3—C8B—H8B2109.5C11D—C10D—C9D121.5 (4)
C1B—C8B—H8B1109.5C12D—C11D—C10D121.8 (4)
H8B3—C8B—H8B1109.5C12D—C11D—H11D119.1
H8B2—C8B—H8B1109.5C10D—C11D—H11D119.1
N2B—C9B—C10B116.6 (4)C11D—C12D—C13D120.0 (4)
N2B—C9B—C16B123.5 (4)C11D—C12D—H12D120.0
C10B—C9B—C16B119.8 (4)C13D—C12D—H12D120.0
C11B—C10B—C15B118.2 (4)O1D—C13D—C14D124.5 (4)
C11B—C10B—C9B120.6 (4)O1D—C13D—C12D115.6 (4)
C15B—C10B—C9B121.2 (4)C14D—C13D—C12D119.9 (4)
C12B—C11B—C10B120.7 (5)C15D—C14D—C13D119.0 (4)
C12B—C11B—H11B119.6C15D—C14D—H14D120.5
C10B—C11B—H11B119.6C13D—C14D—H14D120.5
C11B—C12B—C13B120.6 (4)C14D—C15D—C10D122.4 (4)
C11B—C12B—H12B119.7C14D—C15D—H15D118.8
C13B—C12B—H12B119.7C10D—C15D—H15D118.8
O1B—C13B—C14B130.0 (5)C9D—C16D—H16L109.5
O1B—C13B—C12B110.8 (5)C9D—C16D—H16K109.5
C14B—C13B—C12B119.1 (4)H16L—C16D—H16K109.5
O1B—C13B—Cl1E16.2 (3)C9D—C16D—H16J109.5
C14B—C13B—Cl1E114.1 (4)H16L—C16D—H16J109.5
C12B—C13B—Cl1E126.8 (4)H16K—C16D—H16J109.5
C15B—C14B—C13B120.5 (5)O1D—C17D—H17I109.5
C15B—C14B—H14B119.8O1D—C17D—H17H109.5
C13B—C14B—H14B119.8H17I—C17D—H17H109.5
C14B—C15B—C10B121.0 (4)O1D—C17D—H17G109.5
C14B—C15B—H15B119.5H17I—C17D—H17G109.5
C10B—C15B—H15B119.5H17H—C17D—H17G109.5
C9B—C16B—H16F109.5O1B—Cl1E—C17B143.7 (10)
C9B—C16B—H16E109.5O1B—Cl1E—C13B32.4 (5)
H16F—C16B—H16E109.5C17B—Cl1E—C13B112.7 (7)
C9B—C16B—H16D109.5Cl1B—O1E—C5B129.2 (10)
H16F—C16B—H16D109.5Cl1B—O1E—C17E22.0 (8)
H16E—C16B—H16D109.5C5B—O1E—C17E110.9 (8)
Cl1E—C17B—O1B16.5 (5)Cl1B—C17E—O1E17.5 (6)
C13C—O1C—C17C118.5 (3)
C1A—N1A—N2A—C9A136.5 (4)N2C—N1C—C1C—C8C4.3 (6)
N2A—N1A—C1A—C2A178.4 (3)N1C—C1C—C2C—C3C175.6 (4)
N2A—N1A—C1A—C8A5.3 (6)C8C—C1C—C2C—C3C2.1 (6)
N1A—C1A—C2A—C7A14.2 (6)N1C—C1C—C2C—C7C3.2 (6)
C8A—C1A—C2A—C7A169.3 (4)C8C—C1C—C2C—C7C179.1 (4)
N1A—C1A—C2A—C3A164.7 (4)C7C—C2C—C3C—C4C0.0 (7)
C8A—C1A—C2A—C3A11.7 (6)C1C—C2C—C3C—C4C178.8 (5)
C7A—C2A—C3A—C4A1.2 (7)C2C—C3C—C4C—C5C0.6 (8)
C1A—C2A—C3A—C4A177.8 (4)C3C—C4C—C5C—C6C1.0 (8)
C2A—C3A—C4A—C5A0.3 (8)C3C—C4C—C5C—Cl1C178.6 (4)
C3A—C4A—C5A—C6A0.3 (7)C4C—C5C—C6C—C7C0.8 (8)
C3A—C4A—C5A—Cl1A179.2 (4)Cl1C—C5C—C6C—C7C178.8 (4)
C4A—C5A—C6A—C7A0.1 (7)C5C—C6C—C7C—C2C0.2 (8)
Cl1A—C5A—C6A—C7A178.8 (3)C3C—C2C—C7C—C6C0.3 (7)
C5A—C6A—C7A—C2A1.1 (7)C1C—C2C—C7C—C6C178.6 (4)
C3A—C2A—C7A—C6A1.6 (6)N1C—N2C—C9C—C10C179.5 (3)
C1A—C2A—C7A—C6A177.4 (4)N1C—N2C—C9C—C16C3.3 (6)
N1A—N2A—C9A—C10A178.0 (3)N2C—C9C—C10C—C15C15.4 (6)
N1A—N2A—C9A—C16A2.8 (6)C16C—C9C—C10C—C15C167.2 (4)
N2A—C9A—C10A—C15A7.9 (6)N2C—C9C—C10C—C11C161.9 (4)
C16A—C9A—C10A—C15A172.9 (4)C16C—C9C—C10C—C11C15.5 (6)
N2A—C9A—C10A—C11A171.1 (4)C15C—C10C—C11C—C12C0.6 (6)
C16A—C9A—C10A—C11A8.1 (6)C9C—C10C—C11C—C12C178.0 (4)
C15A—C10A—C11A—C12A0.8 (6)C10C—C11C—C12C—C13C0.0 (6)
C9A—C10A—C11A—C12A179.8 (4)C17C—O1C—C13C—C14C2.1 (6)
C10A—C11A—C12A—C13A0.4 (7)C17C—O1C—C13C—C12C177.5 (4)
C17A—O1A—C13A—C12A179.7 (5)C11C—C12C—C13C—O1C179.9 (4)
C17A—O1A—C13A—C14A0.3 (7)C11C—C12C—C13C—C14C0.6 (6)
C11A—C12A—C13A—O1A179.4 (4)O1C—C13C—C14C—C15C179.9 (4)
C11A—C12A—C13A—C14A0.0 (7)C12C—C13C—C14C—C15C0.4 (6)
O1A—C13A—C14A—C15A179.3 (4)C13C—C14C—C15C—C10C0.2 (6)
C12A—C13A—C14A—C15A0.0 (7)C11C—C10C—C15C—C14C0.8 (6)
C13A—C14A—C15A—C10A0.4 (7)C9C—C10C—C15C—C14C178.1 (4)
C11A—C10A—C15A—C14A0.8 (7)C1D—N1D—N2D—C9D134.7 (4)
C9A—C10A—C15A—C14A179.8 (4)N2D—N1D—C1D—C8D3.0 (6)
C1B—N1B—N2B—C9B137.0 (4)N2D—N1D—C1D—C2D178.1 (3)
N2B—N1B—C1B—C2B178.0 (4)N1D—C1D—C2D—C7D3.9 (6)
N2B—N1B—C1B—C8B4.4 (6)C8D—C1D—C2D—C7D177.2 (4)
N1B—C1B—C2B—C7B7.6 (6)N1D—C1D—C2D—C3D175.2 (4)
C8B—C1B—C2B—C7B174.6 (4)C8D—C1D—C2D—C3D3.8 (6)
N1B—C1B—C2B—C3B172.4 (4)C7D—C2D—C3D—C4D0.1 (7)
C8B—C1B—C2B—C3B5.4 (6)C1D—C2D—C3D—C4D179.2 (4)
C7B—C2B—C3B—C4B0.1 (7)C2D—C3D—C4D—C5D0.5 (7)
C1B—C2B—C3B—C4B179.9 (4)C3D—C4D—C5D—C6D0.9 (7)
C2B—C3B—C4B—C5B0.2 (8)C3D—C4D—C5D—Cl1D178.3 (4)
C3B—C4B—C5B—O1E177.3 (7)C4D—C5D—C6D—C7D0.9 (7)
C3B—C4B—C5B—C6B0.4 (8)Cl1D—C5D—C6D—C7D178.3 (4)
C3B—C4B—C5B—Cl1B178.4 (4)C5D—C6D—C7D—C2D0.4 (7)
C17E—Cl1B—C5B—O1E155 (2)C3D—C2D—C7D—C6D0.0 (6)
O1E—Cl1B—C5B—C4B13.8 (17)C1D—C2D—C7D—C6D179.1 (4)
C17E—Cl1B—C5B—C4B168.9 (12)N1D—N2D—C9D—C10D179.0 (4)
O1E—Cl1B—C5B—C6B167.3 (18)N1D—N2D—C9D—C16D3.7 (6)
C17E—Cl1B—C5B—C6B12.2 (13)N2D—C9D—C10D—C15D14.4 (6)
O1E—C5B—C6B—C7B176.5 (8)C16D—C9D—C10D—C15D168.2 (4)
C4B—C5B—C6B—C7B0.2 (8)N2D—C9D—C10D—C11D160.5 (4)
Cl1B—C5B—C6B—C7B178.7 (4)C16D—C9D—C10D—C11D16.8 (6)
C3B—C2B—C7B—C6B0.3 (7)C15D—C10D—C11D—C12D1.8 (7)
C1B—C2B—C7B—C6B179.7 (4)C9D—C10D—C11D—C12D176.9 (4)
C5B—C6B—C7B—C2B0.1 (8)C10D—C11D—C12D—C13D0.3 (7)
N1B—N2B—C9B—C10B178.3 (4)C17D—O1D—C13D—C14D0.8 (7)
N1B—N2B—C9B—C16B5.2 (6)C17D—O1D—C13D—C12D177.4 (5)
N2B—C9B—C10B—C11B162.0 (4)C11D—C12D—C13D—O1D179.6 (4)
C16B—C9B—C10B—C11B14.6 (6)C11D—C12D—C13D—C14D1.3 (7)
N2B—C9B—C10B—C15B15.2 (6)O1D—C13D—C14D—C15D179.5 (4)
C16B—C9B—C10B—C15B168.1 (4)C12D—C13D—C14D—C15D1.4 (7)
C15B—C10B—C11B—C12B0.4 (6)C13D—C14D—C15D—C10D0.1 (7)
C9B—C10B—C11B—C12B177.0 (4)C11D—C10D—C15D—C14D1.7 (6)
C10B—C11B—C12B—C13B0.5 (7)C9D—C10D—C15D—C14D176.9 (4)
Cl1E—O1B—C13B—C14B10.9 (14)C13B—O1B—Cl1E—C17B22 (2)
C17B—O1B—C13B—C14B3.1 (9)C17B—O1B—Cl1E—C13B22 (2)
Cl1E—O1B—C13B—C12B172.5 (10)O1B—C17B—Cl1E—C13B12.5 (13)
C17B—O1B—C13B—C12B179.7 (5)C14B—C13B—Cl1E—O1B170.9 (12)
C17B—O1B—C13B—Cl1E7.8 (8)C12B—C13B—Cl1E—O1B8.8 (11)
C11B—C12B—C13B—O1B178.4 (5)O1B—C13B—Cl1E—C17B166.2 (15)
C11B—C12B—C13B—C14B1.4 (7)C14B—C13B—Cl1E—C17B4.7 (9)
C11B—C12B—C13B—Cl1E178.9 (4)C12B—C13B—Cl1E—C17B175.0 (8)
O1B—C13B—C14B—C15B177.8 (5)C17E—Cl1B—O1E—C5B38 (3)
C12B—C13B—C14B—C15B1.4 (7)C5B—Cl1B—O1E—C17E38 (3)
Cl1E—C13B—C14B—C15B178.9 (4)C4B—C5B—O1E—Cl1B168.2 (15)
C13B—C14B—C15B—C10B0.6 (7)C6B—C5B—O1E—Cl1B15 (2)
C11B—C10B—C15B—C14B0.4 (6)C4B—C5B—O1E—C17E177.5 (9)
C9B—C10B—C15B—C14B177.0 (4)C6B—C5B—O1E—C17E0.9 (14)
C13B—O1B—C17B—Cl1E162.4 (19)Cl1B—C5B—O1E—C17E14.4 (12)
C1C—N1C—N2C—C9C134.7 (4)C5B—Cl1B—C17E—O1E21.6 (17)
N2C—N1C—C1C—C2C178.2 (4)C5B—O1E—C17E—Cl1B149 (2)

Experimental details

Crystal data
Chemical formulaC17H17ClN2O
Mr300.78
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)6.3260 (3), 31.465 (2), 7.6680 (4)
α, β, γ (°)90.264 (1), 95.891 (1), 90.154 (1)
V3)1518.21 (14)
Z4
Radiation typeMo Kα
µ (mm1)0.25
Crystal size (mm)0.40 × 0.25 × 0.15
Data collection
DiffractometerSiemens SMART CCD area-detector
diffractometer
Absorption correctionEmpirical (using intensity measurements)
(SADABS; Blessing, 1995)
Tmin, Tmax0.81, 0.96
No. of measured, independent and
observed [I > 2σ(I)] reflections
7704, 7704, 7038
Rint0.017
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.05, 0.13, 1.11
No. of reflections7704
No. of parameters760
No. of restraints?
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.32, 0.30
Absolute structureFlack (1983)
Absolute structure parameter0.02 (7)

Computer programs: SMART (Bruker, 1998), SMART, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97.

Selected geometric parameters (Å, º) top
Cl1A—C5A1.748 (5)Cl1C—C5C1.740 (4)
O1A—C13A1.368 (5)O1C—C13C1.372 (5)
N1A—C1A1.300 (6)N1C—C1C1.283 (5)
N1A—N2A1.396 (5)N1C—N2C1.400 (5)
N2A—C9A1.297 (6)N2C—C9C1.289 (6)
C1A—C2A1.490 (6)C1C—C2C1.488 (5)
C9A—C10A1.481 (6)C9C—C10C1.488 (5)
Cl1B—C5B1.826 (6)Cl1D—C5D1.738 (5)
O1B—C13B1.323 (7)O1D—C13D1.374 (5)
N1B—C1B1.284 (6)N1D—C1D1.299 (5)
N1B—N2B1.404 (5)N1D—N2D1.392 (5)
N2B—C9B1.299 (5)N2D—C9D1.288 (5)
C1B—C2B1.478 (7)C1D—C2D1.497 (6)
C9B—C10B1.485 (6)C9D—C10D1.475 (6)
C1A—N1A—N2A114.5 (4)C1C—N1C—N2C115.6 (3)
C9A—N2A—N1A114.8 (3)C9C—N2C—N1C114.4 (4)
N1A—C1A—C2A115.9 (4)N1C—C1C—C2C116.9 (4)
N2A—C9A—C10A116.6 (4)N2C—C9C—C10C116.4 (4)
C1B—N1B—N2B115.0 (4)C1D—N1D—N2D115.2 (4)
C9B—N2B—N1B114.7 (4)C9D—N2D—N1D114.9 (4)
N1B—C1B—C2B117.1 (4)N1D—C1D—C2D115.7 (4)
N2B—C9B—C10B116.6 (4)N2D—C9D—C10D116.9 (4)
C1A—N1A—N2A—C9A136.5 (4)C1C—N1C—N2C—C9C134.7 (4)
N2A—N1A—C1A—C2A178.4 (3)N2C—N1C—C1C—C2C178.2 (4)
N1A—C1A—C2A—C3A164.7 (4)N1C—C1C—C2C—C3C175.6 (4)
N1A—N2A—C9A—C10A178.0 (3)N1C—N2C—C9C—C10C179.5 (3)
N2A—C9A—C10A—C15A7.9 (6)N2C—C9C—C10C—C15C15.4 (6)
C1B—N1B—N2B—C9B137.0 (4)C1D—N1D—N2D—C9D134.7 (4)
N2B—N1B—C1B—C2B178.0 (4)N2D—N1D—C1D—C2D178.1 (3)
N1B—C1B—C2B—C3B172.4 (4)N1D—C1D—C2D—C3D175.2 (4)
N1B—N2B—C9B—C10B178.3 (4)N1D—N2D—C9D—C10D179.0 (4)
N2B—C9B—C10B—C15B15.2 (6)N2D—C9D—C10D—C15D14.4 (6)
 

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