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The structure of {3-[(4-fluoro­phenyl)­methyl]-1H-benzimidazol-2-ylidene}{1-[2-(4-meth­oxy­phenyl)­ethyl]-4-piperidin-1-io}ammonium tetra­chloro­cuprate(II), (C28H33FN4O)[CuCl4], contains diprotonated cations of astemizole hydrogen bonded to three Cl atoms in two different CuCl42− anions, with Cl...N distances in the range 3.166 (4)–3.203 (4) Å. The geometry around copper is flattened tetrahedral with significantly different Cu—Cl distances which lie in the range 2.1968 (14)–2.2861 (12) Å. The phenyl­ethyl C atoms of the (4-methoxy­phenyl­)ethyl group are disordered indicating the presence of two conformers in the crystals.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100007733/fr1280sup1.cif
Contains datablocks Global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100007733/fr1280Isup2.hkl
Contains datablock I

CCDC reference: 152602

Comment top

Astemizole is the active ingredient of `hismanal', a potent antihistaminic drug which has been classified as a long-lasting drug with 24 h effectiveness and has very little or no drowsiness effects (Casy, 1991). A lack of sedation effects may be attributed to the presence of 4-methoxyphenylethyl-4-piperidinyl moiety in astemizole which may hinder the penetration of the central nervous system by this drug (Richards et al., 1984). Continuing our studies on the influence of anions of transition metals, e.g. CuCl42−, on the conformation of antihistamines effective on H1-receptors (Parvez & Sabir, 1997a,b,c, 1998; Parvez, 1998), we have prepared a dihydro cationic salt of astemizole. In this paper, we report the crystal structure of astemizole tetrachlorocuprate(II), (I). The crystal structure of astemizole in its free form has already been reported (Peeters et al., 1995). \sch

Figure 1 shows an ORTEPII (Johnson, 1976) drawing of (I). The structure is composed of dihydro cations of astemizole and CuCl42− anions. The molecular dimensions in the dihydro astemizole cation are normal and agree well with the corresponding dimensions reported in the literature (Allen et al., 1987). The phenylethyl C atoms are disordered over C20—C27 and C20'-C27' with site occupancy factors 0.490 (6) and 0.510 (6), respectively, indicating the presence of two conformers in the crystals. The separation between pairs of C atoms of the phenylethyl ring is in the range 0.12 Å for C25 and 1.27 Å for C21. The important bond distances are: Csp2—F 1.366 (5), mean Csp3—Csp3 1.515 (10), Csp3—Csp2 1.510 (10), and C—Caromatic 1.383 (12) Å; C22—C27 and C22'-C27' aromatic ring distances were constrained at 1.39 (1) Å. It is interesting to note that C1—N3 [1.316 (5) Å] is clearly a double bond and that in the benzimidazole ring, the mean distances N—Csp2 and N—Caromatic, 1.355 (4) and 1.397 (3) Å, respectively, are significantly different from each other. Moreover, the mean Nsp3—C distance is 1.500 (9) Å, while N—Csp3 and C—Nsp2 distances are 1.481 (5) and 1.452 (5) Å, respectively.

The benzimidazole and fluorophenyl rings are essentially planar with maximum deviations of atoms from the least-squares planes being 0.033 (3) and 0.005 (3) Å, respectively. The dihedral angle between these planes is 67.77 (11)°; the corresponding angle in the two molecules of astemizole are around 79° (Peeters et al., 1995). The six-membered piperidinyl ring in (I) has a classical chair conformation with puckering parameters (Cremer & Pople, 1975) Q = 0.573 (5) Å, θ = 1.9 (5) and ϕ = 67 (17)°. The mean-plane of the methoxy group, which is not disordered, is inclined at 11.7 (7) and 21.5 (6)°, with the phenyl rings C22—C27 and C22'-C27', respectively, for the two conformers present in the crystal. The dihedral angle between the mean-planes of these phenyl rings is 29.2 (3)°.

The CuCl42- anion exhibits a flattened tetrahedral geometry with Cu—Cl distances in the range 2.1968 (14) and 2.2861 (12) Å; the shortest distance being the one for the Cl not involved in any hydrogen bond. There are two types of Cl—Cu—Cl angles in the anion, four angles in the range 97.86 (5)–99.93 (5)° and the remaining two are 130.27 (5) and 137.91 (6)°. Similar geometry for CuCl42- has been reported in the tetrachlorocuprate salts of clemizole (Parvez & Sabir, 1997a), chlorpyramine (Parvez & Sabir, 1997b), triprolidine (Parvez & Sabir, 1997c), dicytosine (Ogawa et al., 1979) and fenethazine (Obata et al., 1985).

The dihydro cation of astemizole is hydrogen bonded to two Cl atoms of the same anion, via its ammonium H atoms [N···Cl 3.203 (4) and 3.166 (4) Å]. It is also hydrogen bonded to a Cl atom of a symmetry-related anion involving the H atom attached to N2 of its benzimidazole ring [N···Cl 3.190 (4) Å]. The details of hydrogen-bonding geometry in (I) have been provided in Table 2.

Experimental top

The title compound was synthesized by adding CuCl2·2H20 (1.0 mmol) to astemizole (2.0 mmol) (Sigma Inc.) in HCl (15 ml, 6.0 M) and boiling for 10 min. The solution was allowed to stand at room temperature yielding yellow prismatic crystals after a few days.

Refinement top

The phenylethyl C atoms of the 4-methoxyphenyl-ethyl group were disordered over two sites C20—C27 and C20'-C27' with site occupancy factors 0.490 (6) and 0.510 (6), respectively, indicating the presence of two conformers in the crystals. The N4—C20/C20', C20/C20'-C21/C21' and C—Caromatic distances in the 4-methoxyphenylethyl group were fixed at 1.48 (1), 1.50 (1) and 1.39 (1) Å, respectively, using the command DFIX and the disordered atoms were refined with isotropic displacement parameters. The H atoms were included in the refinement at idealized positions with C—H 0.95, 0.98 and 0.99 and N—H 0.88 & 0.93 Å and isotropic temperature factors of H atoms were tied to the atoms to which they were bonded.

Computing details top

Data collection: SMART (Siemens, 1994); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: TEXSAN (Molecular Structure Corporation, 1994); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. ORTEPII (Johnson, 1976) drawing of (I) with 50% probability ellipsoids; the disordered atoms C20'-C27' are not shown.
1-[(4-Fluorophenyl)methyl]-N-{1-[2-(4-methoxyphenyl)ethyl]-4-piperidin-4-yl}- 1H-benzimidazol-2-ammonium tetrachloro copper(II). top
Crystal data top
(C28H33FN4O)[CuCl4]F(000) = 1372
Mr = 665.92Dx = 1.512 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 9.1099 (7) ÅCell parameters from 3724 reflections
b = 15.9279 (15) Åθ = 1.6–26.4°
c = 20.5073 (19) ŵ = 1.15 mm1
β = 100.445 (2)°T = 193 K
V = 2926.2 (4) Å3Prism, yellow
Z = 40.17 × 0.13 × 0.05 mm
Data collection top
Bruker P4/RA SMART 1000 CCD
diffractometer
5981 independent reflections
Radiation source: Rotating Anode2704 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.097
Detector resolution: SMART 1000 CCD pixels mm-1θmax = 26.4°, θmin = 1.6°
ω scansh = 411
Absorption correction: multi-scan
(SADABS: Sheldrick, 1996)
k = 1819
Tmin = 0.83, Tmax = 0.95l = 2523
14320 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-atom parameters constrained
S = 0.81 w = 1/[σ2(Fo2) + (0.0236P)2]
where P = (Fo2 + 2Fc2)/3
5981 reflections(Δ/σ)max < 0.001
346 parametersΔρmax = 0.40 e Å3
28 restraintsΔρmin = 0.37 e Å3
Crystal data top
(C28H33FN4O)[CuCl4]V = 2926.2 (4) Å3
Mr = 665.92Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.1099 (7) ŵ = 1.15 mm1
b = 15.9279 (15) ÅT = 193 K
c = 20.5073 (19) Å0.17 × 0.13 × 0.05 mm
β = 100.445 (2)°
Data collection top
Bruker P4/RA SMART 1000 CCD
diffractometer
5981 independent reflections
Absorption correction: multi-scan
(SADABS: Sheldrick, 1996)
2704 reflections with I > 2σ(I)
Tmin = 0.83, Tmax = 0.95Rint = 0.097
14320 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05128 restraints
wR(F2) = 0.101H-atom parameters constrained
S = 0.81Δρmax = 0.40 e Å3
5981 reflectionsΔρmin = 0.37 e Å3
346 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cu10.80119 (6)0.49808 (4)0.74242 (3)0.03002 (16)
Cl10.83502 (15)0.63462 (8)0.74197 (7)0.0567 (4)
Cl20.93417 (15)0.38160 (8)0.73436 (6)0.0542 (4)
Cl30.64178 (12)0.48740 (8)0.64293 (5)0.0401 (3)
Cl40.75888 (13)0.48089 (8)0.84655 (6)0.0444 (4)
F10.6171 (3)0.07953 (19)0.46391 (17)0.0733 (10)
N10.2355 (4)0.3927 (2)0.53508 (17)0.0277 (9)
N20.0790 (4)0.3793 (2)0.60390 (18)0.0292 (9)
H2N0.04350.37340.64080.035*
N30.3390 (4)0.3883 (2)0.64984 (17)0.0298 (9)
H3N0.42630.40280.64070.036*
N40.4683 (4)0.3779 (3)0.85948 (17)0.0432 (11)
H4N0.54680.41220.85260.052*
C10.2257 (5)0.3867 (3)0.5999 (2)0.0265 (11)
C20.0063 (5)0.3824 (3)0.5402 (2)0.0293 (11)
C30.1584 (5)0.3817 (3)0.5184 (2)0.0354 (12)
H30.22570.37590.54850.042*
C40.2094 (5)0.3897 (3)0.4511 (2)0.0380 (13)
H40.31370.39000.43450.046*
C50.1102 (5)0.3974 (3)0.4072 (2)0.0354 (12)
H50.14840.40210.36110.042*
C60.0437 (5)0.3983 (3)0.4294 (2)0.0304 (11)
H60.11150.40390.39950.036*
C70.0924 (5)0.3909 (3)0.4962 (2)0.0253 (11)
C80.3767 (4)0.3956 (3)0.5089 (2)0.0319 (12)
H8A0.45190.42730.54040.038*
H8B0.35910.42640.46630.038*
C90.4393 (5)0.3091 (3)0.4980 (2)0.0286 (11)
C100.5230 (5)0.2649 (3)0.5491 (2)0.0381 (13)
H100.54110.28830.59240.046*
C110.5818 (5)0.1865 (3)0.5386 (3)0.0474 (15)
H110.63840.15560.57410.057*
C120.5553 (5)0.1552 (4)0.4749 (3)0.0481 (15)
C130.4745 (5)0.1966 (3)0.4226 (3)0.0461 (14)
H130.45920.17320.37930.055*
C140.4142 (5)0.2751 (3)0.4343 (2)0.0398 (13)
H140.35600.30520.39880.048*
C150.3339 (5)0.3686 (3)0.7185 (2)0.0269 (11)
H150.24490.33230.71990.032*
C160.3224 (5)0.4478 (3)0.7599 (2)0.0347 (12)
H16A0.40570.48640.75620.042*
H16B0.22750.47720.74290.042*
C170.3285 (6)0.4244 (3)0.8314 (2)0.0449 (14)
H17A0.32260.47600.85760.054*
H17B0.24110.38900.83510.054*
C180.4793 (5)0.3004 (3)0.8200 (2)0.0426 (13)
H18A0.39630.26210.82460.051*
H18B0.57420.27130.83760.051*
C190.4731 (5)0.3203 (3)0.7475 (2)0.0346 (12)
H19A0.56200.35370.74240.041*
H19B0.47580.26720.72250.041*
C200.5085 (12)0.3474 (5)0.9297 (3)0.035 (3)*0.490 (6)
H20A0.59580.30940.93410.042*0.490 (6)
H20B0.42390.31550.94160.042*0.490 (6)
C210.5450 (10)0.4216 (5)0.9760 (3)0.034 (3)*0.490 (6)
H21A0.63180.45200.96480.041*0.490 (6)
H21B0.45900.46060.96970.041*0.490 (6)
C220.5798 (9)0.3945 (7)1.0472 (4)0.032 (3)*0.490 (6)
C230.7241 (12)0.3697 (9)1.0749 (5)0.033 (4)*0.490 (6)
H230.79930.36701.04830.040*0.490 (6)
C240.7574 (13)0.3490 (7)1.1415 (5)0.032 (4)*0.490 (6)
H240.85840.33921.16150.038*0.490 (6)
C250.6464 (10)0.3423 (15)1.1801 (7)0.019 (9)*0.490 (6)
C260.5024 (10)0.3639 (6)1.1507 (4)0.026 (3)*0.490 (6)
H260.42510.36271.17620.032*0.490 (6)
C270.4693 (9)0.3874 (6)1.0845 (4)0.030 (3)*0.490 (6)
H270.36880.39881.06470.036*0.490 (6)
C20'0.4534 (8)0.3711 (6)0.9315 (3)0.032 (3)*0.510 (6)
H20C0.38120.32630.93700.038*0.510 (6)
H20D0.41660.42480.94680.038*0.510 (6)
C21'0.6052 (9)0.3506 (6)0.9717 (4)0.042 (3)*0.510 (6)
H21C0.63450.29420.95830.051*0.510 (6)
H21D0.67800.39130.95970.051*0.510 (6)
C22'0.6194 (9)0.3511 (6)1.0461 (4)0.030 (2)*0.510 (6)
C23'0.7514 (11)0.3763 (8)1.0865 (5)0.028 (4)*0.510 (6)
H23'0.82910.39861.06640.034*0.510 (6)
C24'0.7736 (12)0.3699 (7)1.1546 (5)0.025 (3)*0.510 (6)
H24'0.86880.38111.18070.030*0.510 (6)
C25'0.6540 (12)0.3466 (15)1.1844 (7)0.034 (11)*0.510 (6)
C26'0.5177 (10)0.3259 (6)1.1458 (4)0.026 (2)*0.510 (6)
H26'0.43650.30941.16620.032*0.510 (6)
C27'0.5007 (9)0.3294 (6)1.0772 (4)0.034 (3)*0.510 (6)
H27'0.40630.31681.05090.040*0.510 (6)
O10.6871 (3)0.3313 (2)1.24857 (16)0.0478 (9)
C280.5697 (5)0.3247 (3)1.2852 (2)0.0444 (14)
H28A0.50690.37501.27780.067*
H28B0.61180.31961.33250.067*
H28C0.50930.27501.27060.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0293 (3)0.0359 (3)0.0248 (3)0.0008 (3)0.0046 (2)0.0024 (3)
Cl10.0670 (10)0.0407 (9)0.0562 (10)0.0175 (7)0.0054 (8)0.0020 (7)
Cl20.0674 (9)0.0599 (10)0.0428 (9)0.0283 (7)0.0299 (8)0.0135 (7)
Cl30.0406 (7)0.0546 (9)0.0231 (6)0.0156 (6)0.0007 (5)0.0034 (6)
Cl40.0471 (8)0.0628 (10)0.0256 (7)0.0023 (6)0.0131 (6)0.0005 (6)
F10.062 (2)0.073 (3)0.090 (3)0.0163 (18)0.028 (2)0.016 (2)
N10.035 (2)0.033 (2)0.016 (2)0.0040 (18)0.0083 (19)0.0040 (18)
N20.031 (2)0.039 (2)0.020 (2)0.0044 (18)0.0104 (19)0.0002 (19)
N30.030 (2)0.044 (3)0.016 (2)0.0032 (19)0.0046 (19)0.0007 (19)
N40.060 (3)0.051 (3)0.015 (2)0.020 (2)0.002 (2)0.008 (2)
C10.034 (3)0.027 (3)0.018 (3)0.006 (2)0.005 (2)0.002 (2)
C20.038 (3)0.030 (3)0.020 (3)0.005 (2)0.006 (2)0.003 (2)
C30.025 (3)0.044 (3)0.038 (3)0.004 (2)0.007 (2)0.003 (3)
C40.027 (3)0.049 (3)0.034 (3)0.008 (2)0.005 (3)0.005 (3)
C50.043 (3)0.041 (3)0.019 (3)0.004 (2)0.003 (2)0.002 (2)
C60.034 (3)0.032 (3)0.025 (3)0.002 (2)0.006 (2)0.001 (2)
C70.028 (3)0.032 (3)0.015 (3)0.003 (2)0.000 (2)0.002 (2)
C80.025 (3)0.048 (3)0.024 (3)0.014 (2)0.006 (2)0.000 (2)
C90.019 (2)0.042 (3)0.027 (3)0.008 (2)0.009 (2)0.002 (2)
C100.027 (3)0.058 (4)0.030 (3)0.001 (3)0.007 (2)0.007 (3)
C110.032 (3)0.066 (4)0.046 (4)0.006 (3)0.010 (3)0.007 (3)
C120.029 (3)0.052 (4)0.068 (5)0.002 (3)0.023 (3)0.007 (3)
C130.038 (3)0.063 (4)0.041 (4)0.011 (3)0.018 (3)0.022 (3)
C140.034 (3)0.058 (4)0.027 (3)0.015 (3)0.005 (3)0.006 (3)
C150.038 (3)0.028 (3)0.014 (3)0.001 (2)0.003 (2)0.005 (2)
C160.054 (3)0.030 (3)0.020 (3)0.001 (2)0.008 (3)0.002 (2)
C170.068 (4)0.044 (3)0.025 (3)0.001 (3)0.015 (3)0.003 (3)
C180.053 (3)0.038 (3)0.033 (3)0.000 (3)0.002 (3)0.007 (3)
C190.050 (3)0.029 (3)0.024 (3)0.004 (2)0.003 (3)0.001 (2)
O10.043 (2)0.073 (3)0.026 (2)0.0016 (19)0.0014 (17)0.0157 (19)
C280.059 (3)0.057 (4)0.019 (3)0.018 (3)0.013 (3)0.000 (3)
Geometric parameters (Å, º) top
Cu1—Cl12.1968 (14)C16—H16B0.9900
Cu1—Cl22.2382 (13)C17—H17A0.9900
Cu1—Cl42.2545 (13)C17—H17B0.9900
Cu1—Cl32.2861 (12)C18—C191.511 (6)
F1—C121.366 (5)C18—H18A0.9900
N1—C11.352 (5)C18—H18B0.9900
N1—C71.400 (5)C19—H19A0.9900
N1—C81.481 (5)C19—H19B0.9900
N2—C11.359 (5)C20—C211.514 (6)
N2—C21.394 (5)C20—H20A0.9900
N2—H2N0.8800C20—H20B0.9900
N3—C11.316 (5)C21—C221.500 (6)
N3—C151.452 (5)C21—H21A0.9900
N3—H3N0.8800C21—H21B0.9900
N4—C181.490 (5)C22—C271.375 (6)
N4—C171.496 (6)C22—C231.392 (7)
N4—C201.501 (6)C23—C241.385 (6)
N4—C20'1.512 (6)C23—H230.9500
N4—H4N0.9300C24—C251.396 (6)
C2—C31.377 (5)C24—H240.9500
C2—C71.392 (5)C25—C261.385 (7)
C3—C41.379 (6)C25—O11.396 (14)
C3—H30.9500C26—C271.388 (6)
C4—C51.392 (6)C26—H260.9500
C4—H40.9500C27—H270.9500
C5—C61.393 (5)C20'—C21'1.512 (6)
C5—H50.9500C20'—H20C0.9900
C6—C71.367 (6)C20'—H20D0.9900
C6—H60.9500C21'—C22'1.507 (6)
C8—C91.524 (6)C21'—H21C0.9900
C8—H8A0.9900C21'—H21D0.9900
C8—H8B0.9900C22'—C23'1.389 (6)
C9—C101.373 (6)C22'—C27'1.395 (6)
C9—C141.393 (6)C23'—C24'1.379 (6)
C10—C111.390 (6)C23'—H23'0.9500
C10—H100.9500C24'—C25'1.393 (6)
C11—C121.377 (7)C24'—H24'0.9500
C11—H110.9500C25'—O11.319 (15)
C12—C131.358 (7)C25'—C26'1.386 (7)
C13—C141.404 (6)C26'—C27'1.388 (6)
C13—H130.9500C26'—H26'0.9500
C14—H140.9500C27'—H27'0.9500
C15—C191.510 (5)O1—C281.418 (5)
C15—C161.535 (5)C28—H28A0.9800
C15—H151.0000C28—H28B0.9800
C16—C171.502 (6)C28—H28C0.9800
C16—H16A0.9900
Cl1—Cu1—Cl2137.91 (6)N4—C17—H17B109.2
Cl1—Cu1—Cl499.93 (5)C16—C17—H17B109.2
Cl2—Cu1—Cl499.04 (5)H17A—C17—H17B107.9
Cl1—Cu1—Cl397.86 (5)N4—C18—C19111.6 (4)
Cl2—Cu1—Cl397.89 (5)N4—C18—H18A109.3
Cl4—Cu1—Cl3130.27 (5)C19—C18—H18A109.3
C1—N1—C7109.7 (3)N4—C18—H18B109.3
C1—N1—C8125.1 (4)C19—C18—H18B109.3
C7—N1—C8125.1 (3)H18A—C18—H18B108.0
C1—N2—C2109.1 (4)C15—C19—C18111.9 (4)
C1—N2—H2N125.5C15—C19—H19A109.2
C2—N2—H2N125.5C18—C19—H19A109.2
C1—N3—C15126.3 (4)C15—C19—H19B109.2
C1—N3—H3N116.8C18—C19—H19B109.2
C15—N3—H3N116.8H19A—C19—H19B107.9
C18—N4—C17109.7 (4)N4—C20—C21109.7 (6)
C18—N4—C20103.0 (4)N4—C20—H20A109.7
C17—N4—C20124.9 (5)C21—C20—H20A109.7
C18—N4—C20'119.9 (5)N4—C20—H20B109.7
C17—N4—C20'101.0 (4)C21—C20—H20B109.7
C20—N4—C20'24.3 (4)H20A—C20—H20B108.2
C18—N4—H4N105.9C22—C21—C20111.7 (7)
C17—N4—H4N105.9C22—C21—H21A109.3
C20—N4—H4N105.9C20—C21—H21A109.3
C20'—N4—H4N113.4C22—C21—H21B109.3
N3—C1—N1125.5 (4)C20—C21—H21B109.3
N3—C1—N2126.6 (4)H21A—C21—H21B107.9
N1—C1—N2107.9 (4)C27—C22—C23118.8 (8)
C3—C2—C7121.3 (4)C27—C22—C21121.2 (8)
C3—C2—N2131.4 (4)C23—C22—C21119.8 (8)
C7—C2—N2107.2 (4)C24—C23—C22119.5 (10)
C2—C3—C4117.5 (4)C24—C23—H23120.3
C2—C3—H3121.3C22—C23—H23120.3
C4—C3—H3121.3C23—C24—C25121.7 (12)
C3—C4—C5121.0 (4)C23—C24—H24119.1
C3—C4—H4119.5C25—C24—H24119.1
C5—C4—H4119.5C26—C25—C24117.4 (12)
C4—C5—C6121.5 (4)C26—C25—O1121.8 (9)
C4—C5—H5119.2C24—C25—O1119.4 (9)
C6—C5—H5119.2C25—C26—C27120.9 (10)
C7—C6—C5116.8 (4)C25—C26—H26119.6
C7—C6—H6121.6C27—C26—H26119.6
C5—C6—H6121.6C22—C27—C26121.1 (8)
C6—C7—C2121.9 (4)C22—C27—H27119.5
C6—C7—N1132.0 (4)C26—C27—H27119.5
C2—C7—N1106.1 (4)N4—C20'—C21'108.3 (6)
N1—C8—C9113.5 (3)N4—C20'—H20C110.0
N1—C8—H8A108.9C21'—C20'—H20C110.0
C9—C8—H8A108.9N4—C20'—H20D110.0
N1—C8—H8B108.9C21'—C20'—H20D110.0
C9—C8—H8B108.9H20C—C20'—H20D108.4
H8A—C8—H8B107.7C22'—C21'—C20'117.0 (6)
C10—C9—C14119.4 (5)C22'—C21'—H21C108.1
C10—C9—C8121.4 (4)C20'—C21'—H21C108.1
C14—C9—C8119.1 (4)C22'—C21'—H21D108.1
C9—C10—C11121.2 (5)C20'—C21'—H21D108.1
C9—C10—H10119.4H21C—C21'—H21D107.3
C11—C10—H10119.4C23'—C22'—C27'117.2 (8)
C12—C11—C10117.8 (5)C23'—C22'—C21'120.7 (7)
C12—C11—H11121.1C27'—C22'—C21'122.0 (7)
C10—C11—H11121.1C24'—C23'—C22'122.3 (9)
C13—C12—F1118.6 (5)C24'—C23'—H23'118.8
C13—C12—C11123.4 (5)C22'—C23'—H23'118.8
F1—C12—C11118.0 (5)C23'—C24'—C25'118.8 (11)
C12—C13—C14118.0 (5)C23'—C24'—H24'120.6
C12—C13—H13121.0C25'—C24'—H24'120.6
C14—C13—H13121.0O1—C25'—C26'123.0 (10)
C9—C14—C13120.2 (5)O1—C25'—C24'115.6 (9)
C9—C14—H14119.9C26'—C25'—C24'120.3 (12)
C13—C14—H14119.9C25'—C26'—C27'119.5 (10)
N3—C15—C19108.6 (3)C25'—C26'—H26'120.3
N3—C15—C16112.1 (3)C27'—C26'—H26'120.3
C19—C15—C16109.8 (4)C26'—C27'—C22'121.4 (8)
N3—C15—H15108.8C26'—C27'—H27'119.3
C19—C15—H15108.8C22'—C27'—H27'119.3
C16—C15—H15108.8C25'—O1—C254.0 (16)
C17—C16—C15110.0 (4)C25'—O1—C28119.0 (6)
C17—C16—H16A109.7C25—O1—C28117.0 (5)
C15—C16—H16A109.7O1—C28—H28A109.5
C17—C16—H16B109.7O1—C28—H28B109.5
C15—C16—H16B109.7H28A—C28—H28B109.5
H16A—C16—H16B108.2O1—C28—H28C109.5
N4—C17—C16112.2 (4)H28A—C28—H28C109.5
N4—C17—H17A109.2H28B—C28—H28C109.5
C16—C17—H17A109.2
C15—N3—C1—N1169.3 (4)C17—N4—C18—C1956.4 (5)
C15—N3—C1—N211.1 (7)C20—N4—C18—C19168.6 (5)
C7—N1—C1—N3178.4 (4)C20'—N4—C18—C19172.5 (5)
C8—N1—C1—N35.0 (7)N3—C15—C19—C18177.6 (4)
C7—N1—C1—N21.2 (5)C16—C15—C19—C1854.7 (5)
C8—N1—C1—N2175.4 (4)N4—C18—C19—C1556.2 (5)
C2—N2—C1—N3178.4 (4)C18—N4—C20—C21164.2 (7)
C2—N2—C1—N11.3 (5)C17—N4—C20—C2170.1 (9)
C1—N2—C2—C3176.5 (5)C20'—N4—C20—C2158.7 (11)
C1—N2—C2—C70.8 (5)N4—C20—C21—C22177.6 (7)
C7—C2—C3—C40.1 (7)C20—C21—C22—C2789.6 (12)
N2—C2—C3—C4177.0 (4)C20—C21—C22—C2385.4 (13)
C2—C3—C4—C50.6 (7)C27—C22—C23—C248.3 (19)
C3—C4—C5—C60.8 (7)C21—C22—C23—C24176.6 (10)
C4—C5—C6—C70.3 (7)C22—C23—C24—C258 (2)
C5—C6—C7—C20.2 (6)C23—C24—C25—C265 (3)
C5—C6—C7—N1177.1 (4)C23—C24—C25—O1172.4 (14)
C3—C2—C7—C60.4 (7)C24—C25—C26—C273 (3)
N2—C2—C7—C6178.0 (4)O1—C25—C26—C27169.8 (13)
C3—C2—C7—N1177.6 (4)C23—C22—C27—C266.3 (16)
N2—C2—C7—N10.1 (5)C21—C22—C27—C26178.7 (9)
C1—N1—C7—C6177.0 (5)C25—C26—C27—C223.7 (19)
C8—N1—C7—C66.4 (7)C18—N4—C20'—C21'77.1 (8)
C1—N1—C7—C20.7 (5)C17—N4—C20'—C21'162.3 (7)
C8—N1—C7—C2175.9 (4)C20—N4—C20'—C21'27.2 (10)
C1—N1—C8—C985.8 (5)N4—C20'—C21'—C22'172.9 (7)
C7—N1—C8—C990.3 (5)C20'—C21'—C22'—C23'146.4 (10)
N1—C8—C9—C1082.5 (5)C20'—C21'—C22'—C27'31.4 (13)
N1—C8—C9—C1499.1 (5)C27'—C22'—C23'—C24'8.5 (16)
C14—C9—C10—C110.6 (7)C21'—C22'—C23'—C24'173.5 (10)
C8—C9—C10—C11179.0 (4)C22'—C23'—C24'—C25'8 (2)
C9—C10—C11—C121.0 (7)C23'—C24'—C25'—O1171.7 (13)
C10—C11—C12—C130.4 (8)C23'—C24'—C25'—C26'3 (3)
C10—C11—C12—F1177.8 (4)O1—C25'—C26'—C27'168.0 (14)
F1—C12—C13—C14178.7 (4)C24'—C25'—C26'—C27'1 (3)
C11—C12—C13—C140.5 (8)C25'—C26'—C27'—C22'1.9 (18)
C10—C9—C14—C130.3 (6)C23'—C22'—C27'—C26'5.6 (15)
C8—C9—C14—C13178.1 (4)C21'—C22'—C27'—C26'176.5 (9)
C12—C13—C14—C90.8 (7)C26'—C25'—O1—C2535 (18)
C1—N3—C15—C19140.7 (4)C24'—C25'—O1—C25132 (21)
C1—N3—C15—C1697.8 (5)C26'—C25'—O1—C2825 (2)
N3—C15—C16—C17176.0 (4)C24'—C25'—O1—C28166.8 (12)
C19—C15—C16—C1755.2 (5)C26—C25—O1—C25'108 (21)
C18—N4—C17—C1658.4 (5)C24—C25—O1—C25'59 (18)
C20—N4—C17—C16178.9 (5)C26—C25—O1—C2814 (2)
C20'—N4—C17—C16174.1 (5)C24—C25—O1—C28179.9 (14)
C15—C16—C17—N458.0 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···Cl2i0.882.323.190 (4)170
N3—H3N···Cl30.882.373.203 (4)157
N4—H4N···Cl40.932.243.166 (4)171
Symmetry code: (i) x1, y, z.

Experimental details

Crystal data
Chemical formula(C28H33FN4O)[CuCl4]
Mr665.92
Crystal system, space groupMonoclinic, P21/n
Temperature (K)193
a, b, c (Å)9.1099 (7), 15.9279 (15), 20.5073 (19)
β (°) 100.445 (2)
V3)2926.2 (4)
Z4
Radiation typeMo Kα
µ (mm1)1.15
Crystal size (mm)0.17 × 0.13 × 0.05
Data collection
DiffractometerBruker P4/RA SMART 1000 CCD
diffractometer
Absorption correctionMulti-scan
(SADABS: Sheldrick, 1996)
Tmin, Tmax0.83, 0.95
No. of measured, independent and
observed [I > 2σ(I)] reflections
14320, 5981, 2704
Rint0.097
(sin θ/λ)max1)0.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.101, 0.81
No. of reflections5981
No. of parameters346
No. of restraints28
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.40, 0.37

Computer programs: SMART (Siemens, 1994), SAINT (Siemens, 1995), SAINT, SAPI91 (Fan, 1991), SHELXTL (Sheldrick, 1997), TEXSAN (Molecular Structure Corporation, 1994), SHELXTL.

Selected geometric parameters (Å, º) top
Cu1—Cl12.1968 (14)N2—C11.359 (5)
Cu1—Cl22.2382 (13)N2—C21.394 (5)
Cu1—Cl42.2545 (13)N3—C11.316 (5)
Cu1—Cl32.2861 (12)N3—C151.452 (5)
F1—C121.366 (5)N4—C181.490 (5)
N1—C11.352 (5)N4—C171.496 (6)
N1—C71.400 (5)N4—C201.501 (6)
N1—C81.481 (5)N4—C20'1.512 (6)
Cl1—Cu1—Cl2137.91 (6)C7—N1—C8125.1 (3)
Cl1—Cu1—Cl499.93 (5)C1—N2—C2109.1 (4)
Cl2—Cu1—Cl499.04 (5)C1—N3—C15126.3 (4)
Cl1—Cu1—Cl397.86 (5)C18—N4—C17109.7 (4)
Cl2—Cu1—Cl397.89 (5)C18—N4—C20103.0 (4)
Cl4—Cu1—Cl3130.27 (5)C17—N4—C20124.9 (5)
C1—N1—C7109.7 (3)C18—N4—C20'119.9 (5)
C1—N1—C8125.1 (4)C17—N4—C20'101.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···Cl2i0.882.323.190 (4)170
N3—H3N···Cl30.882.373.203 (4)157
N4—H4N···Cl40.932.243.166 (4)171
Symmetry code: (i) x1, y, z.
 

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