[N,N'-Bis(5-bromo­salicyl­idene)-1,3-di­amino­propane]­nickel(II) and [N,N'-­bis(5-chloro­salicyl­idene)-1,3-­di­amino­propane]copper(II)

The title compounds, {4,4'-di­bromo-2,2'-[1,3-propane­diyl­bis(nitrilo­methyl­idyne-N)]­diphenolato-O,O'}nickel(II), [Ni(C₁₇­H₁₄­Br₂­N₂O₂)], and {4,4'-di­chloro-2,2'-[1,3-pro­pane­diyl­bis­(ni­trilo­methyl­idyne-N)]­di­phen­ol­ato-O,O'}­copper(II), [Cu­(C₁₇­H₁₄­Cl₂­N₂O₂)], lie on crystallographic twofold axes. In both structures, the metal coordination sphere is a tetrahedrally distorted square plane formed by the four-coordinate N₂O₂ donor set of the Schiff base imine-phenol ligands. In the Ni compound, the Ni-O and Ni-N distances are 1.908 (3) and 1.959 (4) Å, respectively, while in the Cu compound, the Cu-O and Cu-N distances are 1.907 (2) and 1.960 (2) Å, respectively. The two Schiff base moieties, which themselves are nearly planar, are inclined at an angle of 29.26 (7)° for the Ni compound and 29.26 (5)° for the Cu compound.

Computing details

For both compounds, data collection: CAD-4 Diffractometer Control Software (Enraf-Nonius, 1993); cell refinement: CAD-4 Diffractometer Control Software; data reduction: REDU4 (Stoe & Cie, 1991); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997).

(I)

Crystal data

[Ni(C17H14Br2N2O2)]	F(000) = 976
Mr = 496.83	Dx = 1.985 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 21.466 (3) Å	Cell parameters from 25 reflections
b = 8.167 (1) Å	θ = 2.7–13.3°
c = 9.495 (3) Å	µ = 5.99 mm^−1
β = 93.07 (2)°	T = 293 K
V = 1662.2 (6) Å^3	Needle, dark blue
Z = 4	0.40 × 0.05 × 0.03 mm

Data collection

Enraf-Nonius CAD4 diffractometer	1016 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
Graphite monochromator	θmax = 26.0°, θmin = 1.9°
ω–2θ scans	h = −26→26
Absorption correction: ψ scan (North et al., 1968)	k = −10→0
Tmin = 0.75, Tmax = 0.84	l = −11→3
2249 measured reflections	3 standard reflections every 120 min
1628 independent reflections	intensity decay: 2.0%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.085	H-atom parameters constrained
S = 0.97	w = 1/[σ^2(Fo^2) + (0.0349P)^2 + 4.1291P] where P = (Fo^2 + 2Fc^2)/3
1628 reflections	(Δ/σ)max < 0.001
114 parameters	Δρmax = 0.71 e Å^−3
1 restraint	Δρmin = −0.38 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ni1	0.5000	0.01666 (9)	0.2500	0.0343 (2)
Br1	0.26976 (3)	0.25243 (7)	−0.31466 (6)	0.0653 (2)
O1	0.44154 (14)	0.1858 (4)	0.2007 (3)	0.0443 (8)
N1	0.45946 (17)	−0.1417 (4)	0.1200 (4)	0.0426 (9)
C1	0.40088 (19)	0.1893 (5)	0.0941 (5)	0.0372 (10)
C2	0.3642 (2)	0.3315 (6)	0.0701 (5)	0.0463 (11)
H2	0.3670	0.4164	0.1354	0.056*
C3	0.3248 (2)	0.3469 (6)	−0.0469 (5)	0.0476 (12)
H3	0.3014	0.4419	−0.0604	0.057*
C4	0.3195 (2)	0.2223 (6)	−0.1454 (5)	0.0446 (11)
C5	0.35041 (19)	0.0772 (6)	−0.1216 (5)	0.0415 (11)
H5	0.3446	−0.0087	−0.1853	0.050*
C6	0.39094 (19)	0.0575 (5)	−0.0010 (4)	0.0372 (10)
C7	0.4187 (2)	−0.1009 (5)	0.0216 (5)	0.0410 (11)
H7	0.4060	−0.1829	−0.0416	0.049*
C8	0.4750 (3)	−0.3182 (6)	0.1268 (6)	0.0656 (16)
H8A	0.4422	−0.3825	0.0794	0.098*	0.50
H8B	0.5139	−0.3403	0.0828	0.098*	0.50
H8C	0.4372	−0.3782	0.1438	0.098*	0.50
H8D	0.4891	−0.3536	0.0364	0.098*	0.50
C9	0.4803 (4)	−0.3760 (10)	0.2739 (8)	0.043 (2)	0.50
H9A	0.4403	−0.3575	0.3138	0.064*	0.50
H9B	0.4859	−0.4937	0.2698	0.064*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0430 (4)	0.0248 (4)	0.0342 (4)	0.000	−0.0050 (3)	0.000
Br1	0.0626 (3)	0.0788 (4)	0.0522 (3)	0.0079 (3)	−0.0189 (2)	0.0031 (3)
O1	0.0536 (19)	0.0359 (16)	0.0417 (18)	0.0043 (14)	−0.0123 (15)	−0.0032 (14)
N1	0.054 (2)	0.032 (2)	0.041 (2)	−0.0004 (17)	−0.0037 (19)	−0.0011 (17)
C1	0.037 (2)	0.040 (2)	0.035 (2)	−0.0031 (19)	0.004 (2)	0.004 (2)
C2	0.048 (3)	0.042 (3)	0.049 (3)	0.004 (2)	0.000 (2)	−0.003 (2)
C3	0.043 (3)	0.049 (3)	0.050 (3)	0.009 (2)	−0.001 (2)	0.002 (3)
C4	0.033 (2)	0.057 (3)	0.043 (3)	0.000 (2)	−0.003 (2)	0.001 (2)
C5	0.042 (3)	0.046 (3)	0.036 (3)	−0.005 (2)	0.002 (2)	−0.005 (2)
C6	0.038 (2)	0.041 (3)	0.033 (2)	−0.0041 (19)	0.0002 (19)	−0.002 (2)
C7	0.051 (3)	0.035 (2)	0.037 (3)	−0.009 (2)	0.002 (2)	−0.005 (2)
C8	0.106 (5)	0.030 (3)	0.060 (4)	0.013 (3)	−0.001 (3)	−0.004 (3)
C9	0.048 (6)	0.033 (5)	0.049 (6)	−0.007 (4)	0.014 (5)	0.004 (4)

Geometric parameters (Å, º)

Ni1—O1^i	1.908 (3)	C3—H3	0.9300
Ni1—O1	1.908 (3)	C4—C5	1.371 (6)
Ni1—N1	1.959 (4)	C5—C6	1.410 (6)
Ni1—N1^i	1.959 (4)	C5—H5	0.9300
Br1—C4	1.897 (4)	C6—C7	1.436 (6)
O1—C1	1.300 (5)	C7—H7	0.9300
O1—Ni1^i	1.908 (3)	C8—C9	1.473 (7)
N1—C7	1.289 (6)	C8—H8A	0.9700
N1—C8	1.480 (6)	C8—H8B	0.9700
N1—Ni1^i	1.959 (4)	C8—H8C	0.9700
C1—C2	1.415 (6)	C8—H8D	0.9700
C1—C6	1.414 (6)	C9—C8^i	1.390 (10)
C2—C3	1.365 (6)	C9—H8C	1.5041
C2—H2	0.9300	C9—H9A	0.9700
C3—C4	1.383 (6)	C9—H9B	0.9700
O1^i—Ni1—O1	87.23 (18)	C1—C6—C7	122.9 (4)
O1^i—Ni1—N1	153.75 (14)	N1—C7—C6	127.0 (4)
O1—Ni1—N1	93.39 (14)	N1—C7—H7	116.5
O1^i—Ni1—N1^i	93.39 (14)	C6—C7—H7	116.5
O1—Ni1—N1^i	153.75 (14)	C9—C8—N1	111.0 (5)
N1—Ni1—N1^i	97.4 (2)	C9—C8—H8A	106.5
C1—O1—Ni1^i	127.8 (3)	N1—C8—H8A	110.5
C1—O1—Ni1	127.8 (3)	C9—C8—H8B	108.9
C7—N1—C8	115.2 (4)	N1—C8—H8B	111.1
C7—N1—Ni1^i	123.2 (3)	H8A—C8—H8B	108.6
C8—N1—Ni1^i	121.6 (3)	C9—C8—H8C	72.7
C7—N1—Ni1	123.2 (3)	N1—C8—H8C	108.0
C8—N1—Ni1	121.6 (3)	H8A—C8—H8C	37.8
O1—C1—C2	119.2 (4)	H8B—C8—H8C	136.5
O1—C1—C6	123.5 (4)	C9—C8—H8D	137.0
C2—C1—C6	117.3 (4)	N1—C8—H8D	109.4
C3—C2—C1	121.5 (4)	H8A—C8—H8D	71.4
C3—C2—H2	119.3	H8B—C8—H8D	41.1
C1—C2—H2	119.3	H8C—C8—H8D	107.5
C2—C3—C4	120.5 (4)	C8^i—C9—C8	123.4 (7)
C2—C3—H3	119.7	C8^i—C9—H8C	158.9
C4—C3—H3	119.7	C8—C9—H8C	38.0
C5—C4—C3	120.2 (4)	C8^i—C9—H9A	106.0
C5—C4—Br1	119.8 (4)	C8—C9—H9A	107.2
C3—C4—Br1	120.0 (3)	H8C—C9—H9A	78.6
C4—C5—C6	120.3 (4)	C8^i—C9—H9B	106.4
C4—C5—H5	119.9	C8—C9—H9B	106.4
C6—C5—H5	119.9	H8C—C9—H9B	91.6
C5—C6—C1	119.9 (4)	H9A—C9—H9B	106.5
C5—C6—C7	117.2 (4)
O1^i—Ni1—O1—C1	140.6 (4)	C3—C4—C5—C6	−4.1 (7)
N1—Ni1—O1—C1	−13.2 (4)	Br1—C4—C5—C6	175.6 (3)
N1^i—Ni1—O1—C1	−127.4 (4)	C4—C5—C6—C1	−1.5 (6)
O1^i—Ni1—N1—C7	−76.2 (5)	C4—C5—C6—C7	176.3 (4)
O1—Ni1—N1—C7	14.4 (4)	O1—C1—C6—C5	−173.7 (4)
N1^i—Ni1—N1—C7	170.4 (4)	C2—C1—C6—C5	6.2 (6)
O1^i—Ni1—N1—C8	102.3 (5)	O1—C1—C6—C7	8.7 (7)
O1—Ni1—N1—C8	−167.1 (4)	C2—C1—C6—C7	−171.5 (4)
N1^i—Ni1—N1—C8	−11.1 (3)	C8—N1—C7—C6	173.8 (5)
Ni1^i—O1—C1—C2	−175.8 (3)	Ni1^i—N1—C7—C6	−7.5 (7)
Ni1—O1—C1—C2	−175.8 (3)	Ni1—N1—C7—C6	−7.5 (7)
Ni1^i—O1—C1—C6	4.1 (6)	C5—C6—C7—N1	175.8 (4)
Ni1—O1—C1—C6	4.1 (6)	C1—C6—C7—N1	−6.6 (7)
O1—C1—C2—C3	174.3 (4)	C7—N1—C8—C9	−138.5 (6)
C6—C1—C2—C3	−5.6 (7)	Ni1^i—N1—C8—C9	42.8 (7)
C1—C2—C3—C4	0.3 (7)	Ni1—N1—C8—C9	42.8 (7)
C2—C3—C4—C5	4.7 (7)	N1—C8—C9—C8^i	−63.1 (8)
C2—C3—C4—Br1	−174.9 (4)

Symmetry code: (i) −x+1, y, −z+1/2.

(II)

Crystal data

[Cu(C17H14Cl2N2O2)]	F(000) = 836
Mr = 412.74	Dx = 1.706 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 21.022 (3) Å	Cell parameters from 25 reflections
b = 8.140 (2) Å	θ = 1.9–15.9°
c = 9.416 (3) Å	µ = 1.70 mm^−1
β = 94.06 (2)°	T = 293 K
V = 1607.2 (7) Å^3	Needle, blue
Z = 4	0.30 × 0.08 × 0.08 mm

Data collection

Enraf-Nonius CAD4 diffractometer	1274 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.017
Graphite monochromator	θmax = 26.0°, θmin = 1.9°
ω–2θ scans	h = −25→25
Absorption correction: ψ scan (North et al., 1968)	k = −10→0
Tmin = 0.79, Tmax = 0.87	l = −11→2
1946 measured reflections	3 standard reflections every 90 min
1568 independent reflections	intensity decay: 3.0%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.106	H-atom parameters constrained
S = 1.13	w = 1/[σ^2(Fo^2) + (0.0648P)^2 + 0.4477P] where P = (Fo^2 + 2Fc^2)/3
1568 reflections	(Δ/σ)max < 0.001
114 parameters	Δρmax = 0.57 e Å^−3
0 restraints	Δρmin = −0.51 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.5000	0.01949 (5)	0.2500	0.0383 (2)
Cl1	0.26844 (4)	0.25493 (13)	−0.31366 (10)	0.0677 (3)
O1	0.43986 (10)	0.1888 (2)	0.1998 (2)	0.0437 (5)
N1	0.45778 (12)	−0.1393 (3)	0.1182 (3)	0.0414 (6)
C1	0.39829 (13)	0.1928 (3)	0.0911 (3)	0.0385 (6)
C2	0.36059 (14)	0.3360 (4)	0.0647 (4)	0.0451 (7)
H2	0.3632	0.4208	0.1310	0.054*
C3	0.32081 (14)	0.3526 (4)	−0.0549 (4)	0.0493 (7)
H3	0.2973	0.4485	−0.0701	0.059*
C4	0.31524 (14)	0.2263 (4)	−0.1545 (3)	0.0460 (7)
C5	0.34610 (14)	0.0812 (4)	−0.1291 (3)	0.0443 (7)
H5	0.3397	−0.0052	−0.1932	0.053*
C6	0.38767 (13)	0.0608 (4)	−0.0063 (3)	0.0383 (6)
C7	0.41575 (14)	−0.0988 (3)	0.0187 (3)	0.0417 (7)
H7	0.4019	−0.1817	−0.0440	0.050*
C8	0.4736 (2)	−0.3162 (4)	0.1249 (4)	0.0666 (10)
H8A	0.4401	−0.3787	0.0734	0.100*	0.50
H8B	0.5129	−0.3377	0.0803	0.100*	0.50
H8C	0.4347	−0.3718	0.1475	0.100*	0.50
H8D	0.4841	−0.3562	0.0324	0.100*	0.50
C9	0.4800 (3)	−0.3741 (7)	0.2732 (6)	0.0434 (14)	0.50
H9A	0.4392	−0.3549	0.3125	0.065*	0.50
H9B	0.4854	−0.4924	0.2690	0.065*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0500 (3)	0.0293 (3)	0.0349 (3)	0.000	−0.0022 (2)	0.000
Cl1	0.0667 (6)	0.0803 (7)	0.0528 (5)	0.0089 (4)	−0.0193 (4)	0.0026 (4)
O1	0.0588 (12)	0.0342 (10)	0.0364 (11)	0.0039 (9)	−0.0085 (9)	−0.0036 (8)
N1	0.0562 (14)	0.0299 (11)	0.0376 (13)	−0.0006 (10)	0.0001 (11)	−0.0023 (10)
C1	0.0405 (14)	0.0384 (14)	0.0369 (15)	−0.0044 (11)	0.0047 (12)	0.0027 (12)
C2	0.0491 (16)	0.0395 (15)	0.0467 (17)	0.0027 (12)	0.0033 (13)	−0.0019 (13)
C3	0.0465 (16)	0.0493 (17)	0.0512 (19)	0.0060 (13)	−0.0018 (14)	0.0034 (15)
C4	0.0386 (15)	0.0571 (19)	0.0418 (17)	−0.0010 (13)	−0.0010 (12)	0.0010 (14)
C5	0.0458 (16)	0.0512 (16)	0.0357 (15)	−0.0076 (13)	0.0029 (13)	−0.0026 (13)
C6	0.0404 (14)	0.0397 (14)	0.0351 (15)	−0.0048 (11)	0.0053 (12)	0.0002 (12)
C7	0.0553 (17)	0.0359 (14)	0.0342 (15)	−0.0105 (13)	0.0043 (13)	−0.0048 (12)
C8	0.111 (3)	0.0299 (15)	0.059 (2)	0.0099 (17)	0.000 (2)	−0.0050 (15)
C9	0.056 (4)	0.030 (3)	0.045 (4)	−0.002 (2)	0.005 (3)	0.002 (2)

Geometric parameters (Å, º)

Cu1—O1^i	1.907 (2)	C4—C5	1.361 (4)
Cu1—O1	1.907 (2)	C5—C6	1.409 (4)
Cu1—N1	1.960 (2)	C5—H5	0.9300
Cu1—N1^i	1.960 (2)	C6—C7	1.439 (4)
Cl1—C4	1.749 (3)	C7—H7	0.9300
O1—C1	1.298 (4)	C8—C9	1.471 (6)
N1—C7	1.284 (4)	C8—H8A	0.9700
N1—C8	1.478 (4)	C8—H8B	0.9700
C1—C6	1.420 (4)	C8—H8C	0.9700
C1—C2	1.422 (4)	C8—H8D	0.9700
C2—C3	1.361 (4)	C9—C8^i	1.401 (7)
C2—H2	0.9300	C9—H8C	1.4651
C3—C4	1.391 (5)	C9—H9A	0.9700
C3—H3	0.9300	C9—H9B	0.9700
O1^i—Cu1—O1	87.44 (12)	N1—C7—C6	127.2 (3)
O1^i—Cu1—N1	153.63 (10)	N1—C7—H7	116.4
O1—Cu1—N1	93.27 (10)	C6—C7—H7	116.4
O1^i—Cu1—N1^i	93.27 (10)	N1—C8—C9	111.0 (3)
O1—Cu1—N1^i	153.63 (10)	N1—C8—H8A	109.7
N1—Cu1—N1^i	97.51 (14)	C9—C8—H8A	108.7
C1—O1—Cu1	127.66 (18)	N1—C8—H8B	110.7
C7—N1—C8	115.0 (3)	C9—C8—H8B	109.2
C7—N1—Cu1	123.34 (19)	H8A—C8—H8B	107.5
C8—N1—Cu1	121.7 (2)	N1—C8—H8C	105.9
O1—C1—C6	123.8 (3)	C9—C8—H8C	70.4
O1—C1—C2	119.6 (3)	H8A—C8—H8C	43.4
C6—C1—C2	116.5 (3)	H8B—C8—H8C	140.2
C3—C2—C1	121.9 (3)	N1—C8—H8D	110.7
C3—C2—H2	119.1	C9—C8—H8D	137.2
C1—C2—H2	119.1	H8A—C8—H8D	65.1
C2—C3—C4	120.1 (3)	H8B—C8—H8D	45.1
C2—C3—H3	119.9	H8C—C8—H8D	106.9
C4—C3—H3	119.9	C8^i—C9—C8	123.7 (4)
C5—C4—C3	120.4 (3)	C8^i—C9—H8C	158.4
C5—C4—Cl1	119.9 (3)	C8—C9—H8C	38.6
C3—C4—Cl1	119.6 (3)	C8^i—C9—H9A	106.0
C4—C5—C6	120.5 (3)	C8—C9—H9A	106.6
C4—C5—H5	119.8	H8C—C9—H9A	76.4
C6—C5—H5	119.8	C8^i—C9—H9B	106.5
C5—C6—C1	120.1 (3)	C8—C9—H9B	106.4
C5—C6—C7	117.6 (3)	H8C—C9—H9B	92.9
C1—C6—C7	122.2 (3)	H9A—C9—H9B	106.5
O1^i—Cu1—O1—C1	139.6 (3)	C3—C4—C5—C6	−4.5 (5)
N1—Cu1—O1—C1	−14.0 (2)	Cl1—C4—C5—C6	175.3 (2)
N1^i—Cu1—O1—C1	−128.2 (3)	C4—C5—C6—C1	−0.8 (4)
O1^i—Cu1—N1—C7	−76.4 (3)	C4—C5—C6—C7	176.3 (3)
O1—Cu1—N1—C7	14.5 (3)	O1—C1—C6—C5	−173.8 (3)
N1^i—Cu1—N1—C7	170.4 (3)	C2—C1—C6—C5	5.9 (4)
O1^i—Cu1—N1—C8	102.3 (3)	O1—C1—C6—C7	9.3 (4)
O1—Cu1—N1—C8	−166.9 (3)	C2—C1—C6—C7	−171.0 (3)
N1^i—Cu1—N1—C8	−11.0 (2)	C8—N1—C7—C6	174.8 (3)
Cu1—O1—C1—C6	4.7 (4)	Cu1—N1—C7—C6	−6.5 (4)
Cu1—O1—C1—C2	−175.0 (2)	C5—C6—C7—N1	174.9 (3)
O1—C1—C2—C3	173.6 (3)	C1—C6—C7—N1	−8.1 (5)
C6—C1—C2—C3	−6.2 (4)	C7—N1—C8—C9	−138.7 (4)
C1—C2—C3—C4	1.1 (5)	Cu1—N1—C8—C9	42.6 (5)
C2—C3—C4—C5	4.4 (5)	N1—C8—C9—C8^i	−62.9 (6)
C2—C3—C4—Cl1	−175.4 (3)

Symmetry code: (i) −x+1, y, −z+1/2.