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Acta Cryst. (2011). E67, m765    [ doi:10.1107/S1600536811017752 ]

Chlorido(1H-imidazole-[kappa]N3)bis(triphenylphosphane-[kappa]P)copper(I)

M. Hossaini Sadr, R. Kia and B. Soltani

Abstract top

In the title complex, [CuCl(C3H4N2)(C18H15P)2], the coordination geometry around CuI is distorted tetrahedral formed by two triphenylphosphane ligands, an imidazole ligand and a chloride group. An intramolecular C-H...Cl interaction occurs. The crystal packing is stabilized by intermolecular N-H...Cl hydrogen bonds, which form an extended chain parallel to [010].

Comment top

The chemistry of copper complexes with nitrogen-containing ligands especially pyrazole and imidazole derived ligands has been attracting continuous attention due to their rich coordination properties (Trofimenko, 1993; Sadimenko et al., 1996) and show good models of the active sites of copper proteins (Pettinari, 2001; Hossaini Sadr et al., 2005; Kitajima, 1992; Kitajima et al., 1989).

The asymmetric unit of the title complex, Fig. 1, comprises one molecule of the complex. The bond lengths (Allen, et al., 1987) and angles are within the normal ranges. The geometry around CuI is that of distorted tetrahedral which is coordinated by two triphenylphosphanes, imidazole and chloro groups. The crystal packing is stabilized by the intermolecular N—H···Cl hydrogen bonds (Table 2) which makes an extended chain along the [0 1 0] direction (Fig. 2).

Related literature top

For standard bond lengths, see: Allen et al. (1987). For background to the use of imidazole-derived ligands in coordination chemistry, see, for example; Trofimenko (1993); Sadimenko & Basson (1996); Pettinari (2001); Hossaini Sadr et al. (2005); Kitajima (1992); Kitajima et al. (1989).

Experimental top

PPh3 (2 mmol, 0.53 g) was added to a solution of CuCl (1 mmol, 0.09 g) and imidazole (2 mmol, 0.07 g) in dry CH3OH/CH3CN (1:1) (30 ml) and stirred for 12 h under N2 atmosphere. The filtrate of the resulting mixture was left to evaporate slowly at ambient temperature. Single crystals suitable for X-ray diffraction analysis were obtained after 4 days.

Refinement top

All hydrogen atoms were positioned geometrically with C–H = 0.93 Å and included in a riding model approximation with Uiso (H) = 1.2 Ueq (C), except the N-bound H atom which was located from the difference Fourier map and constrained to refine with the parent atom with Uiso (H) = 1.2 Ueq (N).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2009); cell refinement: X-AREA (Stoe & Cie, 2009); data reduction: X-AREA (Stoe & Cie, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The ORTEP plot of the title compound, showing 40% probability displacement ellipsoids and the atomic numbering.
[Figure 2] Fig. 2. The packing diagram of the title compound viewed down the c-axis showing an extended chain along the b-axis. The dashed lines show the hyrogen bonding interactions.
Chloro(1H-imidazole-N)bis(triphenylphosphane)copper(I) top
Crystal data top
[CuCl(C3H4N2)(C18H15P)2]F(000) = 1432
Mr = 691.61Dx = 1.347 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ynCell parameters from 5052 reflections
a = 13.674 (5) Åθ = 1.9–29.5°
b = 12.407 (5) ŵ = 0.84 mm−1
c = 20.353 (5) ÅT = 296 K
β = 98.956 (5)°Block, pale-yellow
V = 3411 (2) Å30.42 × 0.41 × 0.35 mm
Z = 4
Data collection top
Stoe IPDS 2T Image Plate
diffractometer		9190 independent reflections
Radiation source: fine-focus sealed tube6720 reflections with I > 2σ(I)
graphiteRint = 0.053
Detector resolution: 0.15 mm pixels mm-1θmax = 29.2°, θmin = 1.7°
ω scansh = −18→18
Absorption correction: multi-scan
(MULABS in PLATON; Blessing, 1995; Spek, 2009)		k = −16→15
Tmin = 0.879, Tmax = 1.000l = −27→27
24488 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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0542P)2 + 0.4442P]
where P = (Fo2 + 2Fc2)/3
9190 reflections(Δ/σ)max = 0.002
409 parametersΔρmax = 0.42 e Å−3
0 restraintsΔρmin = −0.58 e Å−3
Crystal data top
[CuCl(C3H4N2)(C18H15P)2]V = 3411 (2) Å3
Mr = 691.61Z = 4
Monoclinic, P21/nMo Kα radiation
a = 13.674 (5) ŵ = 0.84 mm−1
b = 12.407 (5) ÅT = 296 K
c = 20.353 (5) Å0.42 × 0.41 × 0.35 mm
β = 98.956 (5)°
Data collection top
Stoe IPDS 2T Image Plate
diffractometer		9190 independent reflections
Absorption correction: multi-scan
(MULABS in PLATON; Blessing, 1995; Spek, 2009)		6720 reflections with I > 2σ(I)
Tmin = 0.879, Tmax = 1.000Rint = 0.053
24488 measured reflectionsθmax = 29.2°
Refinement top
R[F2 > 2σ(F2)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.112Δρmax = 0.42 e Å−3
S = 1.02Δρmin = −0.58 e Å−3
9190 reflectionsAbsolute structure: ?
409 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.841807 (18)0.32155 (2)0.629310 (13)0.03820 (8)
Cl10.79523 (5)0.50608 (5)0.61438 (3)0.05424 (16)
P10.78372 (4)0.23056 (5)0.53392 (3)0.03740 (12)
P21.00039 (4)0.31129 (5)0.68142 (3)0.03835 (12)
N10.75543 (15)0.27483 (17)0.69960 (10)0.0480 (5)
N20.6971 (2)0.1876 (2)0.77835 (12)0.0645 (7)
H20.692 (2)0.141 (3)0.8046 (17)0.077*
C10.6682 (2)0.3194 (2)0.70903 (15)0.0613 (7)
H1A0.63840.37830.68580.074*
C20.6310 (3)0.2653 (3)0.75720 (18)0.0791 (10)
H2A0.57160.27900.77260.095*
C30.7705 (2)0.1959 (2)0.74322 (13)0.0551 (6)
H3A0.82600.15150.74870.066*
C40.64932 (15)0.2413 (2)0.50960 (12)0.0442 (5)
C50.6049 (2)0.3378 (3)0.5176 (2)0.0946 (14)
H5A0.64220.39530.53720.114*
C60.5037 (3)0.3503 (3)0.4965 (3)0.139 (2)
H6A0.47470.41740.50020.167*
C70.4468 (2)0.2669 (3)0.4707 (2)0.0949 (13)
H7A0.37910.27610.45710.114*
C80.4895 (2)0.1700 (3)0.4650 (2)0.0797 (10)
H8A0.45080.11160.44840.096*
C90.59015 (19)0.1571 (3)0.48383 (17)0.0677 (8)
H9A0.61860.09000.47900.081*
C100.80015 (15)0.08445 (19)0.54037 (12)0.0437 (5)
C110.7684 (2)0.0338 (2)0.59392 (16)0.0611 (7)
H11A0.74320.07530.62550.073*
C120.7731 (2)−0.0765 (2)0.60157 (18)0.0713 (8)
H12A0.7500−0.10900.63740.086*
C130.8120 (2)−0.1378 (3)0.5563 (2)0.0774 (9)
H13A0.8155−0.21230.56120.093*
C140.8456 (3)−0.0897 (3)0.5040 (2)0.0855 (10)
H14A0.8725−0.13170.47350.103*
C150.8403 (2)0.0216 (2)0.49573 (16)0.0667 (8)
H15A0.86390.05350.45990.080*
C160.83088 (15)0.26438 (18)0.45733 (11)0.0408 (5)
C170.7717 (2)0.2776 (3)0.39636 (13)0.0675 (8)
H17A0.70400.26510.39240.081*
C180.8118 (2)0.3093 (3)0.34108 (15)0.0787 (10)
H18A0.77060.31870.30060.094*
C190.9107 (2)0.3267 (2)0.34536 (15)0.0645 (7)
H19A0.93710.34750.30790.077*
C200.9710 (2)0.3138 (2)0.40473 (16)0.0634 (7)
H20A1.03870.32600.40780.076*
C210.93172 (17)0.2824 (2)0.46077 (13)0.0519 (6)
H21A0.97350.27330.50100.062*
C221.09967 (15)0.33598 (18)0.63312 (11)0.0399 (5)
C231.08348 (18)0.4148 (2)0.58503 (12)0.0495 (5)
H23A1.02280.45020.57780.059*
C241.1553 (2)0.4422 (2)0.54744 (15)0.0617 (7)
H24A1.14290.49560.51510.074*
C251.2447 (2)0.3910 (2)0.55775 (15)0.0637 (7)
H25A1.29310.40910.53220.076*
C261.26349 (19)0.3128 (3)0.60565 (16)0.0650 (8)
H26A1.32480.27870.61270.078*
C271.19130 (18)0.2841 (2)0.64382 (14)0.0533 (6)
H27A1.20410.23080.67620.064*
C281.03301 (17)0.40460 (19)0.75114 (11)0.0443 (5)
C291.13038 (19)0.4304 (2)0.77678 (14)0.0593 (7)
H29A1.18200.39880.75880.071*
C301.1511 (2)0.5028 (3)0.82877 (15)0.0708 (8)
H30A1.21650.51870.84600.085*
C311.0763 (3)0.5510 (3)0.85505 (15)0.0723 (9)
H31A1.09070.59910.89030.087*
C320.9796 (3)0.5282 (3)0.82932 (16)0.0743 (9)
H32A0.92870.56180.84680.089*
C330.9575 (2)0.4556 (2)0.77755 (13)0.0593 (7)
H33A0.89180.44080.76040.071*
C341.02986 (16)0.1780 (2)0.71692 (13)0.0484 (5)
C351.0459 (2)0.1579 (3)0.78493 (16)0.0744 (9)
H35A1.04390.21380.81520.089*
C361.0649 (3)0.0526 (4)0.8071 (2)0.1134 (17)
H36A1.07570.03830.85250.136*
C371.0679 (3)−0.0304 (3)0.7627 (3)0.1120 (17)
H37A1.0827−0.09990.77840.134*
C381.0494 (3)−0.0118 (3)0.6959 (2)0.0887 (11)
H38A1.0499−0.06840.66600.106*
C391.0300 (2)0.0912 (2)0.67346 (17)0.0652 (7)
H39A1.01660.10360.62790.078*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.03717 (13)0.04272 (15)0.03490 (14)−0.00243 (11)0.00620 (10)−0.00078 (12)
Cl10.0774 (4)0.0389 (3)0.0486 (3)0.0017 (3)0.0166 (3)−0.0012 (3)
P10.0326 (2)0.0410 (3)0.0380 (3)−0.0004 (2)0.0035 (2)−0.0058 (2)
P20.0369 (3)0.0426 (3)0.0343 (3)−0.0024 (2)0.0017 (2)0.0001 (2)
N10.0501 (10)0.0520 (12)0.0441 (10)−0.0047 (9)0.0144 (8)0.0072 (9)
N20.0835 (17)0.0596 (15)0.0553 (14)−0.0193 (13)0.0257 (12)0.0128 (12)
C10.0656 (16)0.0573 (16)0.0669 (17)0.0049 (13)0.0290 (14)0.0147 (14)
C20.083 (2)0.077 (2)0.089 (2)0.0050 (17)0.0530 (19)0.0175 (19)
C30.0586 (14)0.0569 (15)0.0504 (14)−0.0049 (12)0.0105 (11)0.0117 (12)
C40.0331 (10)0.0519 (13)0.0474 (12)−0.0006 (9)0.0060 (9)−0.0091 (11)
C50.0411 (14)0.0577 (19)0.179 (4)0.0039 (12)−0.0005 (19)−0.032 (2)
C60.0459 (17)0.081 (3)0.280 (7)0.0192 (17)−0.004 (3)−0.054 (4)
C70.0331 (13)0.107 (3)0.141 (4)0.0036 (15)0.0012 (17)−0.040 (3)
C80.0421 (13)0.088 (2)0.104 (3)−0.0121 (14)−0.0022 (15)−0.029 (2)
C90.0454 (13)0.0660 (18)0.087 (2)0.0011 (12)−0.0038 (13)−0.0250 (16)
C100.0361 (10)0.0427 (12)0.0501 (13)0.0011 (9)−0.0002 (9)−0.0070 (10)
C110.0649 (16)0.0502 (15)0.0710 (18)−0.0048 (12)0.0199 (14)−0.0026 (14)
C120.0708 (18)0.0534 (17)0.089 (2)−0.0063 (14)0.0104 (16)0.0109 (16)
C130.0659 (18)0.0459 (16)0.116 (3)0.0061 (13)−0.0002 (18)−0.0003 (18)
C140.096 (2)0.0576 (19)0.106 (3)0.0208 (17)0.026 (2)−0.0171 (19)
C150.0796 (19)0.0543 (16)0.0686 (19)0.0126 (14)0.0187 (15)−0.0082 (14)
C160.0374 (10)0.0439 (12)0.0408 (11)0.0020 (9)0.0048 (8)−0.0045 (10)
C170.0475 (14)0.108 (2)0.0440 (14)−0.0136 (15)−0.0012 (11)0.0036 (16)
C180.0737 (19)0.120 (3)0.0405 (14)−0.0134 (19)0.0038 (13)0.0014 (17)
C190.0763 (19)0.0666 (18)0.0568 (16)0.0084 (15)0.0296 (14)0.0046 (14)
C200.0471 (13)0.0696 (18)0.079 (2)0.0083 (12)0.0257 (13)0.0076 (16)
C210.0375 (11)0.0632 (15)0.0545 (14)0.0064 (10)0.0055 (10)0.0048 (12)
C220.0396 (10)0.0418 (12)0.0374 (11)−0.0018 (8)0.0026 (8)−0.0023 (9)
C230.0491 (12)0.0506 (14)0.0495 (13)0.0009 (10)0.0096 (10)0.0051 (11)
C240.0745 (18)0.0568 (16)0.0589 (16)−0.0055 (14)0.0259 (14)0.0065 (13)
C250.0661 (16)0.0640 (17)0.0680 (18)−0.0150 (14)0.0329 (14)−0.0115 (15)
C260.0436 (13)0.0723 (19)0.082 (2)0.0039 (12)0.0178 (13)−0.0128 (17)
C270.0457 (12)0.0578 (15)0.0563 (15)0.0030 (11)0.0079 (11)−0.0002 (12)
C280.0492 (12)0.0478 (13)0.0345 (11)−0.0056 (10)0.0019 (9)0.0005 (10)
C290.0520 (14)0.0678 (18)0.0548 (15)−0.0040 (12)−0.0024 (11)−0.0105 (13)
C300.0719 (18)0.078 (2)0.0575 (17)−0.0211 (16)−0.0073 (14)−0.0140 (16)
C310.101 (2)0.0676 (19)0.0473 (16)−0.0198 (17)0.0103 (16)−0.0161 (14)
C320.087 (2)0.080 (2)0.0597 (18)−0.0072 (17)0.0245 (16)−0.0227 (16)
C330.0596 (15)0.0727 (18)0.0467 (14)−0.0055 (13)0.0118 (12)−0.0107 (13)
C340.0382 (11)0.0486 (13)0.0548 (14)−0.0080 (10)−0.0037 (10)0.0095 (12)
C350.086 (2)0.069 (2)0.0578 (17)−0.0182 (16)−0.0219 (15)0.0199 (15)
C360.139 (4)0.086 (3)0.093 (3)−0.034 (3)−0.049 (3)0.044 (2)
C370.107 (3)0.058 (2)0.150 (4)−0.018 (2)−0.045 (3)0.039 (3)
C380.085 (2)0.0477 (17)0.128 (4)−0.0038 (16)−0.001 (2)0.005 (2)
C390.0669 (17)0.0502 (16)0.077 (2)−0.0024 (13)0.0069 (15)0.0041 (15)
Geometric parameters (Å, °) top
Cu1—N12.0746 (18)C17—C181.382 (4)
Cu1—P22.2643 (9)C17—H17A0.9300
Cu1—P12.2792 (8)C18—C191.359 (4)
Cu1—Cl12.3831 (11)C18—H18A0.9300
P1—C161.826 (2)C19—C201.362 (4)
P1—C101.829 (3)C19—H19A0.9300
P1—C41.832 (2)C20—C211.390 (4)
P2—C221.822 (2)C20—H20A0.9300
P2—C341.824 (3)C21—H21A0.9300
P2—C281.832 (2)C22—C231.376 (3)
N1—C31.316 (3)C22—C271.395 (3)
N1—C11.355 (3)C23—C241.379 (3)
N2—C31.324 (3)C23—H23A0.9300
N2—C21.346 (4)C24—C251.365 (4)
N2—H20.80 (3)C24—H24A0.9300
C1—C21.351 (4)C25—C261.371 (4)
C1—H1A0.9300C25—H25A0.9300
C2—H2A0.9300C26—C271.394 (4)
C3—H3A0.9300C26—H26A0.9300
C4—C51.364 (4)C27—H27A0.9300
C4—C91.375 (4)C28—C331.389 (3)
C5—C61.392 (5)C28—C291.390 (3)
C5—H5A0.9300C29—C301.383 (4)
C6—C71.351 (5)C29—H29A0.9300
C6—H6A0.9300C30—C311.363 (4)
C7—C81.349 (5)C30—H30A0.9300
C7—H7A0.9300C31—C321.373 (5)
C8—C91.380 (4)C31—H31A0.9300
C8—H8A0.9300C32—C331.383 (4)
C9—H9A0.9300C32—H32A0.9300
C10—C151.375 (3)C33—H33A0.9300
C10—C111.385 (4)C34—C351.390 (4)
C11—C121.379 (4)C34—C391.394 (4)
C11—H11A0.9300C35—C361.394 (5)
C12—C131.365 (5)C35—H35A0.9300
C12—H12A0.9300C36—C371.374 (7)
C13—C141.361 (5)C36—H36A0.9300
C13—H13A0.9300C37—C381.363 (6)
C14—C151.392 (4)C37—H37A0.9300
C14—H14A0.9300C38—C391.370 (4)
C15—H15A0.9300C38—H38A0.9300
C16—C171.381 (3)C39—H39A0.9300
C16—C211.388 (3)
N1—Cu1—P2105.54 (6)C21—C16—P1118.29 (18)
N1—Cu1—P1106.78 (6)C16—C17—C18121.0 (3)
P2—Cu1—P1123.54 (2)C16—C17—H17A119.5
N1—Cu1—Cl1100.77 (6)C18—C17—H17A119.5
P2—Cu1—Cl1109.34 (3)C19—C18—C17120.6 (3)
P1—Cu1—Cl1108.45 (3)C19—C18—H18A119.7
C16—P1—C10103.49 (10)C17—C18—H18A119.7
C16—P1—C4103.02 (11)C18—C19—C20119.8 (3)
C10—P1—C4101.45 (10)C18—C19—H19A120.1
C16—P1—Cu1119.39 (8)C20—C19—H19A120.1
C10—P1—Cu1114.03 (8)C19—C20—C21120.2 (3)
C4—P1—Cu1113.32 (8)C19—C20—H20A119.9
C22—P2—C34103.23 (11)C21—C20—H20A119.9
C22—P2—C28101.52 (10)C16—C21—C20120.8 (2)
C34—P2—C28104.71 (12)C16—C21—H21A119.6
C22—P2—Cu1118.53 (8)C20—C21—H21A119.6
C34—P2—Cu1111.89 (7)C23—C22—C27118.7 (2)
C28—P2—Cu1115.29 (8)C23—C22—P2116.89 (17)
C3—N1—C1104.9 (2)C27—C22—P2124.39 (18)
C3—N1—Cu1128.80 (18)C22—C23—C24121.4 (2)
C1—N1—Cu1126.30 (17)C22—C23—H23A119.3
C3—N2—C2107.4 (2)C24—C23—H23A119.3
C3—N2—H2125 (2)C25—C24—C23119.9 (3)
C2—N2—H2128 (2)C25—C24—H24A120.1
C2—C1—N1109.9 (3)C23—C24—H24A120.1
C2—C1—H1A125.1C24—C25—C26120.2 (2)
N1—C1—H1A125.1C24—C25—H25A119.9
N2—C2—C1106.1 (3)C26—C25—H25A119.9
N2—C2—H2A127.0C25—C26—C27120.5 (3)
C1—C2—H2A127.0C25—C26—H26A119.8
N1—C3—N2111.7 (3)C27—C26—H26A119.8
N1—C3—H3A124.1C26—C27—C22119.5 (3)
N2—C3—H3A124.1C26—C27—H27A120.3
C5—C4—C9117.8 (2)C22—C27—H27A120.3
C5—C4—P1118.6 (2)C33—C28—C29118.5 (2)
C9—C4—P1123.61 (19)C33—C28—P2118.78 (18)
C4—C5—C6120.1 (3)C29—C28—P2122.68 (19)
C4—C5—H5A120.0C30—C29—C28120.4 (3)
C6—C5—H5A120.0C30—C29—H29A119.8
C7—C6—C5121.3 (3)C28—C29—H29A119.8
C7—C6—H6A119.4C31—C30—C29120.6 (3)
C5—C6—H6A119.4C31—C30—H30A119.7
C8—C7—C6119.0 (3)C29—C30—H30A119.7
C8—C7—H7A120.5C30—C31—C32119.7 (3)
C6—C7—H7A120.5C30—C31—H31A120.1
C7—C8—C9120.5 (3)C32—C31—H31A120.1
C7—C8—H8A119.8C31—C32—C33120.6 (3)
C9—C8—H8A119.8C31—C32—H32A119.7
C4—C9—C8121.3 (3)C33—C32—H32A119.7
C4—C9—H9A119.4C32—C33—C28120.2 (3)
C8—C9—H9A119.4C32—C33—H33A119.9
C15—C10—C11118.0 (3)C28—C33—H33A119.9
C15—C10—P1124.9 (2)C35—C34—C39118.6 (3)
C11—C10—P1117.12 (19)C35—C34—P2123.2 (2)
C12—C11—C10121.6 (3)C39—C34—P2118.1 (2)
C12—C11—H11A119.2C34—C35—C36118.8 (4)
C10—C11—H11A119.2C34—C35—H35A120.6
C13—C12—C11119.6 (3)C36—C35—H35A120.6
C13—C12—H12A120.2C37—C36—C35120.9 (4)
C11—C12—H12A120.2C37—C36—H36A119.5
C14—C13—C12119.9 (3)C35—C36—H36A119.5
C14—C13—H13A120.1C38—C37—C36120.5 (4)
C12—C13—H13A120.1C38—C37—H37A119.7
C13—C14—C15120.9 (3)C36—C37—H37A119.7
C13—C14—H14A119.6C37—C38—C39119.2 (4)
C15—C14—H14A119.6C37—C38—H38A120.4
C10—C15—C14120.1 (3)C39—C38—H38A120.4
C10—C15—H15A120.0C38—C39—C34121.9 (3)
C14—C15—H15A120.0C38—C39—H39A119.0
C17—C16—C21117.7 (2)C34—C39—H39A119.0
C17—C16—P1123.99 (17)
N1—Cu1—P1—C16171.86 (10)C13—C14—C15—C10−0.4 (6)
P2—Cu1—P1—C16−65.76 (9)C10—P1—C16—C1797.1 (3)
Cl1—Cu1—P1—C1664.03 (9)C4—P1—C16—C17−8.2 (3)
N1—Cu1—P1—C10−65.17 (10)Cu1—P1—C16—C17−134.9 (2)
P2—Cu1—P1—C1057.21 (8)C10—P1—C16—C21−85.7 (2)
Cl1—Cu1—P1—C10−173.00 (8)C4—P1—C16—C21168.98 (19)
N1—Cu1—P1—C450.22 (11)Cu1—P1—C16—C2142.3 (2)
P2—Cu1—P1—C4172.60 (9)C21—C16—C17—C18−0.9 (5)
Cl1—Cu1—P1—C4−57.61 (9)P1—C16—C17—C18176.3 (3)
N1—Cu1—P2—C22175.02 (10)C16—C17—C18—C190.8 (6)
P1—Cu1—P2—C2252.08 (9)C17—C18—C19—C20−0.5 (5)
Cl1—Cu1—P2—C22−77.34 (9)C18—C19—C20—C210.3 (5)
N1—Cu1—P2—C3455.07 (11)C17—C16—C21—C200.7 (4)
P1—Cu1—P2—C34−67.87 (10)P1—C16—C21—C20−176.7 (2)
Cl1—Cu1—P2—C34162.71 (10)C19—C20—C21—C16−0.4 (4)
N1—Cu1—P2—C28−64.44 (11)C34—P2—C22—C23161.39 (19)
P1—Cu1—P2—C28172.63 (8)C28—P2—C22—C23−90.3 (2)
Cl1—Cu1—P2—C2843.21 (9)Cu1—P2—C22—C2337.1 (2)
P2—Cu1—N1—C3−41.3 (2)C34—P2—C22—C27−21.6 (2)
P1—Cu1—N1—C391.7 (2)C28—P2—C22—C2786.7 (2)
Cl1—Cu1—N1—C3−155.1 (2)Cu1—P2—C22—C27−145.94 (19)
P2—Cu1—N1—C1140.4 (2)C27—C22—C23—C240.5 (4)
P1—Cu1—N1—C1−86.6 (2)P2—C22—C23—C24177.6 (2)
Cl1—Cu1—N1—C126.6 (2)C22—C23—C24—C25−0.1 (4)
C3—N1—C1—C2−1.3 (4)C23—C24—C25—C26−0.4 (5)
Cu1—N1—C1—C2177.4 (2)C24—C25—C26—C270.6 (5)
C3—N2—C2—C1−0.3 (4)C25—C26—C27—C22−0.3 (4)
N1—C1—C2—N21.0 (4)C23—C22—C27—C26−0.3 (4)
C1—N1—C3—N21.1 (3)P2—C22—C27—C26−177.2 (2)
Cu1—N1—C3—N2−177.48 (18)C22—P2—C28—C33144.4 (2)
C2—N2—C3—N1−0.6 (4)C34—P2—C28—C33−108.5 (2)
C16—P1—C4—C5−91.1 (3)Cu1—P2—C28—C3314.9 (2)
C10—P1—C4—C5162.0 (3)C22—P2—C28—C29−32.6 (2)
Cu1—P1—C4—C539.4 (3)C34—P2—C28—C2974.6 (2)
C16—P1—C4—C989.2 (3)Cu1—P2—C28—C29−162.0 (2)
C10—P1—C4—C9−17.7 (3)C33—C28—C29—C302.0 (4)
Cu1—P1—C4—C9−140.3 (2)P2—C28—C29—C30178.9 (2)
C9—C4—C5—C6−3.6 (7)C28—C29—C30—C31−0.9 (5)
P1—C4—C5—C6176.7 (4)C29—C30—C31—C32−0.5 (5)
C4—C5—C6—C73.1 (9)C30—C31—C32—C330.9 (5)
C5—C6—C7—C8−0.5 (9)C31—C32—C33—C280.2 (5)
C6—C7—C8—C9−1.5 (7)C29—C28—C33—C32−1.6 (4)
C5—C4—C9—C81.6 (5)P2—C28—C33—C32−178.7 (2)
P1—C4—C9—C8−178.7 (3)C22—P2—C34—C35121.6 (2)
C7—C8—C9—C41.0 (6)C28—P2—C34—C3515.7 (3)
C16—P1—C10—C150.5 (3)Cu1—P2—C34—C35−109.8 (2)
C4—P1—C10—C15107.1 (2)C22—P2—C34—C39−62.6 (2)
Cu1—P1—C10—C15−130.7 (2)C28—P2—C34—C39−168.5 (2)
C16—P1—C10—C11−178.6 (2)Cu1—P2—C34—C3966.0 (2)
C4—P1—C10—C11−72.0 (2)C39—C34—C35—C362.3 (5)
Cu1—P1—C10—C1150.2 (2)P2—C34—C35—C36178.0 (3)
C15—C10—C11—C12−2.3 (4)C34—C35—C36—C370.0 (6)
P1—C10—C11—C12176.9 (2)C35—C36—C37—C38−1.9 (7)
C10—C11—C12—C131.5 (5)C36—C37—C38—C391.5 (6)
C11—C12—C13—C140.0 (5)C37—C38—C39—C340.8 (5)
C12—C13—C14—C15−0.5 (6)C35—C34—C39—C38−2.7 (4)
C11—C10—C15—C141.7 (4)P2—C34—C39—C38−178.7 (2)
P1—C10—C15—C14−177.4 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2···Cl1i0.80 (4)2.34 (4)3.127 (3)171 (3)
C5—H5A···Cl10.932.783.663 (4)160
Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2···Cl1i0.80 (4)2.34 (4)3.127 (3)171 (3)
C5—H5A···Cl10.932.783.663 (4)160
Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2.
Acknowledgements top

This research was supported by research fund No. 403/313 from Azarbaijan University of Tarbiat Moallem (MHS and BS).

references
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