trans-Bis(2-amino-1,3-benzo­thia­zole-κN³)­di­chloro­copper(II)

The title complex, [CuCl₂(C₇H₆N₂S)₂], contains a Cu centre with a distorted square-planar coordination geometry, involving two Cl ligands and two endocyclic N atoms from the thia­zole moieties [Cu—Cl = 2.275 (2) and 2.297 (2) Å, and Cu—N = 1.986 (5) and 1.988 (5) Å]. The amino groups participate in intra- and intermolecular N—H...Cl hydrogen bonds, with N...Cl distances in the range 3.202 (6)–3.316 (6) Å.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.011 Å
• R factor = 0.038
• wR factor = 0.087
• Data-to-parameter ratio = 9.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.17
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         11
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  S1       =       3.43 Ang.

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           27.56
           From the CIF: _reflns_number_total               1933
           Count of symmetry unique reflns         1935
           Completeness (_total/calc)             99.90%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present          yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: P3 Software (Siemens, 1993); cell refinement: P3 Software; data reduction: XDISK in SHELXTL/PC (Sheldrick, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

trans-Bis(2-amino-1,3-benzothiazole-κN³)dichlorocopper(II)

Crystal data

[CuCl2(C7H6N2S)2]	F(000) = 438
Mr = 434.87	Dx = 1.799 Mg m^−3 Dm = 1.75 (3) Mg m^−3 Dm measured by by flotation
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 15 reflections
a = 6.443 (1) Å	θ = 10.0–15.0°
b = 13.032 (3) Å	µ = 1.96 mm^−1
c = 9.987 (2) Å	T = 293 K
β = 106.85 (2)°	Needle, brown
V = 802.6 (3) Å^3	0.4 × 0.1 × 0.1 mm
Z = 2

Data collection

Siemens P3 diffractometer	1649 reflections with I > 2σ(I)
Radiation source: FK60-10 Siemens Mo tube	Rint = 0.026
Graphite monochromator	θmax = 27.6°, θmin = 2.1°
ω–2θ scans	h = −8→8
Absorption correction: ψ scan (North et al., 1968)	k = 0→16
Tmin = 0.721, Tmax = 0.822	l = 0→12
2096 measured reflections	3 standard reflections every 50 reflections
1933 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.087	w = 1/[σ^2(Fo^2) + (0.0445P)^2 + 0.5431P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
1933 reflections	Δρmax = 0.96 e Å^−3
209 parameters	Δρmin = −0.44 e Å^−3
0 restraints	Absolute structure: Flack (1983)
0 constraints	Absolute structure parameter: 0.08 (3)
Primary atom site location: structure-invariant direct methods

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
Cu	0.73783 (11)	0.05079 (7)	0.61331 (7)	0.0196 (2)
Cl1	0.8332 (3)	−0.11686 (12)	0.65459 (18)	0.0288 (5)
Cl2	0.6521 (3)	0.22182 (12)	0.58044 (19)	0.0316 (5)
S1	0.2715 (3)	0.00982 (14)	0.86922 (19)	0.0332 (5)
S11	1.1973 (3)	0.08683 (13)	0.35171 (18)	0.0327 (5)
N1	0.5828 (8)	0.0435 (5)	0.7584 (5)	0.0225 (12)
N2	0.3261 (8)	−0.0776 (5)	0.6389 (5)	0.0272 (17)
N11	0.8864 (7)	0.0589 (5)	0.4648 (5)	0.0217 (12)
N12	1.1403 (9)	0.1844 (5)	0.5741 (6)	0.0291 (17)
C1	0.4737 (12)	0.0963 (5)	0.9529 (7)	0.0304 (19)
C2	0.6304 (10)	0.1039 (5)	0.8800 (6)	0.0264 (17)
C3	0.8065 (11)	0.1660 (5)	0.9305 (7)	0.030 (2)
C4	0.8340 (14)	0.2187 (6)	1.0554 (8)	0.044 (3)
C5	0.6807 (15)	0.2109 (6)	1.1272 (7)	0.038 (2)
C6	0.4980 (15)	0.1493 (6)	1.0768 (8)	0.044 (3)
C7	0.4045 (10)	−0.0107 (5)	0.7415 (7)	0.0235 (19)
C11	1.0018 (11)	−0.0041 (5)	0.2771 (7)	0.030 (2)
C12	0.8450 (10)	−0.0083 (4)	0.3498 (6)	0.0218 (17)
C13	0.6662 (11)	−0.0730 (5)	0.3036 (7)	0.0303 (19)
C14	0.6463 (12)	−0.1312 (5)	0.1839 (7)	0.035 (2)
C15	0.8005 (15)	−0.1250 (7)	0.1127 (8)	0.042 (3)
C16	0.9807 (13)	−0.0629 (6)	0.1589 (7)	0.040 (2)
C17	1.0626 (10)	0.1143 (4)	0.4768 (6)	0.0228 (17)
H1	0.39330	−0.08900	0.57750	0.0330*
H2	0.20760	−0.10970	0.63430	0.0330*
H3	0.90840	0.17280	0.88150	0.0360*
H4	0.95630	0.25930	1.09080	0.0530*
H5	0.69920	0.24730	1.21000	0.0450*
H6	0.39380	0.14370	1.12420	0.0530*
H11	1.07470	0.19650	0.63610	0.0350*
H12	1.25620	0.21770	0.57560	0.0350*
H13	0.56380	−0.07790	0.35250	0.0360*
H14	0.52770	−0.17460	0.15120	0.0420*
H15	0.78210	−0.16370	0.03180	0.0500*
H16	1.08420	−0.06060	0.11050	0.0470*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu	0.0208 (3)	0.0173 (3)	0.0232 (3)	−0.0009 (3)	0.0102 (2)	0.0001 (3)
Cl1	0.0298 (9)	0.0202 (8)	0.0394 (10)	0.0037 (7)	0.0146 (8)	0.0040 (7)
Cl2	0.0314 (9)	0.0218 (8)	0.0462 (10)	0.0043 (7)	0.0184 (8)	0.0073 (7)
S1	0.0401 (10)	0.0339 (8)	0.0342 (9)	−0.0026 (8)	0.0243 (8)	0.0009 (7)
S11	0.0349 (9)	0.0359 (9)	0.0358 (9)	−0.0040 (7)	0.0238 (7)	0.0010 (7)
N1	0.028 (2)	0.020 (2)	0.023 (2)	−0.005 (2)	0.0131 (19)	−0.003 (2)
N2	0.023 (3)	0.029 (3)	0.031 (3)	−0.007 (2)	0.010 (2)	−0.005 (2)
N11	0.024 (2)	0.019 (2)	0.024 (2)	0.002 (3)	0.0098 (18)	0.004 (3)
N12	0.026 (3)	0.027 (3)	0.039 (3)	−0.007 (2)	0.017 (2)	−0.006 (2)
C1	0.047 (4)	0.024 (3)	0.025 (3)	0.006 (3)	0.018 (3)	0.004 (3)
C2	0.031 (3)	0.023 (3)	0.025 (3)	0.002 (3)	0.008 (3)	0.003 (3)
C3	0.035 (4)	0.028 (4)	0.027 (3)	0.001 (3)	0.007 (3)	0.000 (3)
C4	0.061 (5)	0.029 (4)	0.036 (4)	−0.002 (4)	0.004 (4)	−0.001 (3)
C5	0.063 (5)	0.033 (4)	0.015 (3)	0.010 (4)	0.008 (3)	0.001 (3)
C6	0.069 (6)	0.038 (4)	0.034 (4)	0.010 (4)	0.028 (4)	0.003 (3)
C7	0.023 (3)	0.025 (4)	0.025 (3)	0.003 (3)	0.011 (3)	0.003 (3)
C11	0.038 (4)	0.028 (4)	0.027 (3)	0.000 (3)	0.014 (3)	0.001 (3)
C12	0.032 (3)	0.015 (3)	0.021 (3)	0.004 (3)	0.012 (3)	0.003 (2)
C13	0.034 (4)	0.026 (3)	0.030 (3)	0.001 (3)	0.008 (3)	0.000 (3)
C14	0.045 (4)	0.024 (4)	0.030 (4)	−0.009 (3)	0.001 (3)	−0.001 (3)
C15	0.062 (5)	0.037 (4)	0.029 (4)	0.002 (4)	0.015 (4)	−0.013 (3)
C16	0.050 (4)	0.047 (5)	0.027 (3)	0.008 (4)	0.018 (3)	−0.003 (3)
C17	0.025 (3)	0.020 (3)	0.024 (3)	0.003 (2)	0.008 (2)	0.007 (2)

Geometric parameters (Å, º)

Cu—Cl1	2.2747 (19)	C1—C2	1.409 (10)
Cu—Cl2	2.2969 (19)	C2—C3	1.366 (10)
Cu—N1	1.986 (5)	C3—C4	1.390 (10)
Cu—N11	1.988 (5)	C4—C5	1.382 (13)
S1—C1	1.742 (7)	C5—C6	1.393 (13)
S1—C7	1.751 (7)	C11—C12	1.406 (10)
S11—C11	1.733 (7)	C11—C16	1.381 (10)
S11—C17	1.752 (6)	C12—C13	1.394 (9)
N1—C2	1.405 (8)	C13—C14	1.390 (9)
N1—C7	1.317 (9)	C14—C15	1.382 (12)
N2—C7	1.329 (9)	C15—C16	1.380 (12)
N11—C12	1.407 (8)	C3—H3	0.9299
N11—C17	1.321 (8)	C4—H4	0.9297
N12—C17	1.322 (8)	C5—H5	0.9305
N2—H2	0.8601	C6—H6	0.9297
N2—H1	0.8599	C13—H13	0.9299
N12—H11	0.8594	C14—H14	0.9305
N12—H12	0.8601	C15—H15	0.9304
C1—C6	1.386 (10)	C16—H16	0.9306
Cl1···S1^i	3.433 (3)
Cl1—Cu—Cl2	177.58 (7)	N1—C7—N2	125.0 (6)
Cl1—Cu—N1	89.34 (19)	S1—C7—N2	120.3 (5)
Cl1—Cu—N11	91.32 (19)	S11—C11—C12	110.3 (5)
Cl2—Cu—N1	89.98 (19)	C12—C11—C16	120.8 (7)
Cl2—Cu—N11	89.41 (19)	S11—C11—C16	128.8 (6)
N1—Cu—N11	178.7 (2)	C11—C12—C13	120.1 (6)
C1—S1—C7	89.6 (3)	N11—C12—C13	126.1 (6)
C11—S11—C17	89.9 (3)	N11—C12—C11	113.8 (5)
Cu—N1—C2	125.0 (5)	C12—C13—C14	118.4 (7)
Cu—N1—C7	122.5 (4)	C13—C14—C15	120.7 (7)
C2—N1—C7	112.0 (5)	C14—C15—C16	121.5 (7)
Cu—N11—C12	123.9 (4)	C11—C16—C15	118.4 (7)
Cu—N11—C17	123.3 (4)	N11—C17—N12	125.2 (6)
C12—N11—C17	111.6 (5)	S11—C17—N11	114.4 (4)
H1—N2—H2	120.04	S11—C17—N12	120.3 (5)
C7—N2—H1	120.39	C2—C3—H3	119.99
C7—N2—H2	119.57	C4—C3—H3	119.97
H11—N12—H12	120.05	C3—C4—H4	119.74
C17—N12—H12	120.23	C5—C4—H4	119.93
C17—N12—H11	119.73	C4—C5—H5	119.79
C2—C1—C6	120.9 (7)	C6—C5—H5	119.48
S1—C1—C2	110.2 (5)	C1—C6—H6	120.28
S1—C1—C6	128.8 (7)	C5—C6—H6	121.37
N1—C2—C1	113.4 (6)	C12—C13—H13	120.79
N1—C2—C3	127.0 (6)	C14—C13—H13	120.77
C1—C2—C3	119.6 (6)	C13—C14—H14	119.68
C2—C3—C4	120.0 (7)	C15—C14—H14	119.66
C3—C4—C5	120.3 (8)	C14—C15—H15	119.05
C4—C5—C6	120.7 (7)	C16—C15—H15	119.42
C1—C6—C5	118.4 (8)	C11—C16—H16	121.23
S1—C7—N1	114.7 (5)	C15—C16—H16	120.34
Cl1—Cu—N1—C2	119.9 (5)	C17—N11—C12—C13	−176.3 (6)
Cl1—Cu—N1—C7	−68.8 (5)	Cu—N11—C17—S11	166.2 (3)
Cl2—Cu—N1—C2	−57.8 (5)	Cu—N11—C17—N12	−12.7 (9)
Cl2—Cu—N1—C7	113.6 (5)	C12—N11—C17—S11	−1.6 (7)
Cl1—Cu—N11—C12	54.2 (5)	C12—N11—C17—N12	179.4 (6)
Cl1—Cu—N11—C17	−112.2 (5)	S1—C1—C2—C3	−178.3 (5)
Cl2—Cu—N11—C12	−128.1 (5)	C6—C1—C2—N1	178.7 (6)
Cl2—Cu—N11—C17	65.5 (5)	C6—C1—C2—C3	−1.4 (10)
C7—S1—C1—C2	−0.5 (5)	S1—C1—C6—C5	176.7 (6)
C7—S1—C1—C6	−177.1 (7)	C2—C1—C6—C5	0.4 (11)
C1—S1—C7—N1	−1.0 (6)	S1—C1—C2—N1	1.7 (7)
C1—S1—C7—N2	178.2 (6)	N1—C2—C3—C4	−178.0 (7)
C17—S11—C11—C12	0.4 (5)	C1—C2—C3—C4	2.1 (10)
C17—S11—C11—C16	176.5 (7)	C2—C3—C4—C5	−1.8 (11)
C11—S11—C17—N11	0.7 (5)	C3—C4—C5—C6	0.8 (12)
C11—S11—C17—N12	179.7 (5)	C4—C5—C6—C1	−0.1 (12)
Cu—N1—C2—C1	169.7 (5)	S11—C11—C12—N11	−1.4 (7)
Cu—N1—C2—C3	−10.3 (10)	S11—C11—C12—C13	177.0 (5)
C7—N1—C2—C1	−2.4 (8)	C16—C11—C12—N11	−177.8 (6)
C7—N1—C2—C3	177.6 (7)	S11—C11—C16—C15	−174.9 (6)
Cu—N1—C7—S1	−170.3 (3)	C12—C11—C16—C15	0.8 (11)
Cu—N1—C7—N2	10.6 (10)	C16—C11—C12—C13	0.5 (10)
C2—N1—C7—S1	2.1 (7)	N11—C12—C13—C14	177.2 (6)
C2—N1—C7—N2	−177.1 (6)	C11—C12—C13—C14	−1.0 (9)
Cu—N11—C12—C11	−165.8 (4)	C12—C13—C14—C15	0.1 (10)
Cu—N11—C12—C13	15.9 (9)	C13—C14—C15—C16	1.3 (12)
C17—N11—C12—C11	2.0 (8)	C14—C15—C16—C11	−1.7 (12)

Symmetry code: (i) x+1, y, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···Cl1	0.86	2.74	3.266 (6)	121
N2—H2···Cl1^ii	0.86	2.48	3.265 (6)	152
N12—H11···Cl2	0.86	2.64	3.202 (6)	124
N12—H12···Cl2^i	0.86	2.54	3.316 (6)	151

Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z.