Bis{μ-2,2′-[(3,4-di­thia­hexane-1,6-di­yl)bis­(nitrilo­methanylyl­idene)]bis­(4-bromo­phenolato)-κ⁴O,N,N′,O′}dicopper(II)

The crystal structure of a novel binuclear copper(II) complex with a dianionic Schiff base derived from 5-bromo­salicylic aldehyde and cyste­amine prepared by direct synthesis is reported.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.046
• wR factor = 0.098
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00669 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact Br1      ..S1        .       3.51 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      7.010 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT004_ALERT_5_G Polymeric Structure Found with Maximum Dimension          1 Info
PLAT012_ALERT_1_G N.O.K.   _shelx_res_checksum Found in CIF ......     Please Check
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT045_ALERT_1_G Calculated and Reported Z Differ by a Factor ...       2.00 Check
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          2 Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   3 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
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Bis{µ-2,2'-[(3,4-dithiahexane-1,6-diyl)bis(nitrilomethanylylidene)]bis(4-bromophenolato)-κ⁴O,N,N',O'}dicopper(II)

Crystal data

[Cu2(C18H16Br2N2O2S2)2]	F(000) = 1140
Mr = 1159.61	Dx = 1.923 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.3596 (5) Å	Cell parameters from 2534 reflections
b = 8.3442 (3) Å	θ = 2.7–23.6°
c = 19.5002 (7) Å	µ = 5.31 mm^−1
β = 95.156 (2)°	T = 296 K
V = 2002.94 (13) Å^3	Needle, green
Z = 2	0.45 × 0.10 × 0.06 mm

Data collection

Bruker SMART APEXII diffractometer	3939 independent reflections
Radiation source: sealed tube	2644 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.075
phi and ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan sadabs	h = −15→8
Tmin = 0.36, Tmax = 0.74	k = −10→10
18553 measured reflections	l = −23→24

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.098	w = 1/[σ^2(Fo^2) + (0.0426P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.004
3939 reflections	Δρmax = 0.82 e Å^−3
244 parameters	Δρmin = −0.66 e Å^−3

Special details

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
BR1	1.46222 (5)	0.24549 (7)	0.82836 (3)	0.04443 (19)
BR2	0.40450 (5)	0.21977 (8)	1.11957 (3)	0.0456 (2)
CU1	0.95419 (5)	0.30506 (7)	1.00084 (3)	0.01799 (16)
N1	1.0809 (3)	0.1638 (4)	1.03365 (18)	0.0184 (9)
N2	0.8169 (3)	0.3643 (4)	0.94366 (18)	0.0174 (9)
O1	1.0408 (2)	0.4239 (3)	0.94197 (15)	0.0184 (7)
O2	0.8768 (3)	0.2123 (4)	1.07014 (16)	0.0239 (8)
S1	1.10722 (11)	−0.01078 (14)	1.23102 (6)	0.0231 (3)
S2	1.21861 (10)	−0.17845 (15)	1.20755 (6)	0.0229 (3)
C1	1.1308 (4)	0.3764 (5)	0.9170 (2)	0.0187 (11)
C2	1.1648 (4)	0.4542 (5)	0.8585 (2)	0.0241 (12)
H2	1.120805	0.533137	0.836940	0.029*
C3	1.2610 (4)	0.4166 (6)	0.8324 (2)	0.0279 (13)
H3	1.282029	0.470919	0.794135	0.033*
C4	1.3278 (4)	0.2961 (6)	0.8634 (3)	0.0265 (12)
C5	1.2960 (4)	0.2146 (6)	0.9191 (3)	0.0261 (12)
H5	1.340017	0.133916	0.939219	0.031*
C6	1.1973 (4)	0.2517 (5)	0.9464 (2)	0.0205 (11)
C7	1.1680 (4)	0.1571 (5)	1.0031 (2)	0.0184 (11)
H7	1.218760	0.081147	1.019849	0.022*
C8	0.7732 (4)	0.2183 (5)	1.0778 (2)	0.0193 (11)
C9	0.7380 (4)	0.1630 (6)	1.1407 (2)	0.0260 (12)
H9	0.788849	0.123649	1.174609	0.031*
C10	0.6303 (4)	0.1663 (6)	1.1528 (3)	0.0247 (12)
H10	0.608900	0.131899	1.194901	0.030*
C11	0.5537 (4)	0.2208 (6)	1.1021 (3)	0.0282 (12)
C12	0.5833 (4)	0.2746 (6)	1.0406 (3)	0.0287 (13)
H12	0.530635	0.311494	1.007245	0.034*
C13	0.6938 (4)	0.2746 (5)	1.0273 (2)	0.0214 (11)
C14	0.7216 (4)	0.3439 (5)	0.9635 (2)	0.0206 (11)
H14	0.663784	0.377719	0.933102	0.025*
C15	1.0733 (4)	0.0487 (5)	1.0908 (2)	0.0191 (11)
H15A	1.121681	−0.040961	1.085098	0.023*
H15B	0.999770	0.007538	1.089495	0.023*
C16	1.1034 (4)	0.1278 (6)	1.1595 (2)	0.0222 (12)
H16A	1.051164	0.211612	1.166482	0.027*
H16B	1.174199	0.177672	1.158804	0.027*
C17	0.8220 (4)	0.4465 (5)	0.8773 (2)	0.0219 (11)
H17A	0.865362	0.542817	0.884674	0.026*
H17B	0.749153	0.478879	0.860140	0.026*
C18	0.8697 (4)	0.3449 (5)	0.8229 (2)	0.0212 (11)
H18A	0.939036	0.302111	0.841906	0.025*
H18B	0.883066	0.412405	0.784101	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
BR1	0.0376 (4)	0.0474 (4)	0.0522 (4)	−0.0041 (3)	0.0256 (3)	−0.0010 (3)
BR2	0.0234 (3)	0.0744 (5)	0.0400 (4)	−0.0008 (3)	0.0092 (3)	−0.0080 (3)
CU1	0.0192 (3)	0.0175 (3)	0.0170 (3)	0.0009 (3)	0.0002 (2)	0.0026 (3)
N1	0.028 (2)	0.017 (2)	0.010 (2)	−0.0013 (18)	−0.0003 (18)	−0.0023 (16)
N2	0.024 (2)	0.015 (2)	0.013 (2)	0.0012 (17)	−0.0001 (18)	−0.0034 (16)
O1	0.0209 (19)	0.0170 (18)	0.0174 (17)	0.0007 (14)	0.0019 (15)	0.0013 (14)
O2	0.0197 (19)	0.029 (2)	0.0229 (18)	0.0018 (15)	0.0025 (15)	0.0086 (15)
S1	0.0316 (7)	0.0187 (7)	0.0190 (7)	0.0033 (6)	0.0029 (6)	0.0010 (5)
S2	0.0253 (7)	0.0192 (7)	0.0229 (7)	0.0026 (6)	−0.0044 (6)	−0.0016 (6)
C1	0.022 (3)	0.018 (3)	0.015 (3)	−0.001 (2)	−0.002 (2)	−0.004 (2)
C2	0.037 (3)	0.018 (3)	0.018 (3)	−0.007 (2)	0.004 (2)	0.002 (2)
C3	0.040 (3)	0.026 (3)	0.020 (3)	−0.009 (3)	0.010 (3)	−0.003 (2)
C4	0.029 (3)	0.027 (3)	0.025 (3)	−0.003 (2)	0.010 (2)	−0.006 (2)
C5	0.027 (3)	0.020 (3)	0.031 (3)	−0.001 (2)	0.005 (2)	−0.003 (2)
C6	0.020 (3)	0.022 (3)	0.020 (3)	−0.004 (2)	0.003 (2)	−0.007 (2)
C7	0.017 (3)	0.019 (3)	0.018 (3)	0.004 (2)	−0.002 (2)	0.000 (2)
C8	0.021 (3)	0.014 (3)	0.024 (3)	0.000 (2)	0.004 (2)	−0.006 (2)
C9	0.029 (3)	0.027 (3)	0.022 (3)	0.003 (2)	0.001 (2)	0.004 (2)
C10	0.023 (3)	0.026 (3)	0.026 (3)	−0.006 (2)	0.008 (2)	−0.001 (2)
C11	0.024 (3)	0.033 (3)	0.029 (3)	−0.002 (2)	0.009 (2)	−0.006 (2)
C12	0.021 (3)	0.033 (3)	0.030 (3)	0.001 (2)	−0.003 (2)	−0.003 (2)
C13	0.021 (3)	0.021 (3)	0.022 (3)	−0.002 (2)	−0.002 (2)	−0.002 (2)
C14	0.018 (3)	0.019 (3)	0.023 (3)	0.006 (2)	−0.005 (2)	−0.002 (2)
C15	0.014 (3)	0.017 (3)	0.026 (3)	0.002 (2)	0.002 (2)	0.002 (2)
C16	0.026 (3)	0.021 (3)	0.019 (3)	0.002 (2)	−0.002 (2)	0.003 (2)
C17	0.029 (3)	0.021 (3)	0.015 (3)	0.004 (2)	−0.004 (2)	0.003 (2)
C18	0.024 (3)	0.022 (3)	0.018 (3)	−0.004 (2)	0.001 (2)	0.004 (2)

Geometric parameters (Å, º)

BR1—C4	1.900 (5)	C6—C7	1.433 (6)
BR2—C11	1.905 (5)	C7—H7	0.9300
CU1—O2	1.890 (3)	C8—C13	1.408 (6)
CU1—O1	1.915 (3)	C8—C9	1.415 (6)
CU1—N2	2.006 (4)	C9—C10	1.372 (6)
CU1—N1	2.018 (4)	C9—H9	0.9300
CU1—O1^i	2.520 (3)	C10—C11	1.382 (7)
N1—C7	1.277 (5)	C10—H10	0.9300
N1—C15	1.480 (5)	C11—C12	1.362 (7)
N2—C14	1.284 (5)	C12—C13	1.413 (6)
N2—C17	1.471 (5)	C12—H12	0.9300
O1—C1	1.315 (5)	C13—C14	1.441 (6)
O2—C8	1.304 (5)	C14—H14	0.9300
S1—C16	1.808 (5)	C15—C16	1.511 (6)
S1—S2	2.0435 (17)	C15—H15A	0.9700
S2—C18^ii	1.832 (5)	C15—H15B	0.9700
C1—C2	1.410 (6)	C16—H16A	0.9700
C1—C6	1.415 (6)	C16—H16B	0.9700
C2—C3	1.371 (6)	C17—C18	1.517 (6)
C2—H2	0.9300	C17—H17A	0.9700
C3—C4	1.403 (7)	C17—H17B	0.9700
C3—H3	0.9300	C18—S2^ii	1.832 (5)
C4—C5	1.369 (7)	C18—H18A	0.9700
C5—C6	1.407 (6)	C18—H18B	0.9700
C5—H5	0.9300
O2—CU1—O1	170.63 (14)	C13—C8—C9	117.8 (4)
O2—CU1—N2	92.36 (15)	C10—C9—C8	121.4 (5)
O1—CU1—N2	91.68 (14)	C10—C9—H9	119.3
O2—CU1—N1	87.85 (14)	C8—C9—H9	119.3
O1—CU1—N1	91.88 (14)	C9—C10—C11	119.7 (5)
N2—CU1—N1	156.01 (14)	C9—C10—H10	120.1
O2—CU1—O1^i	92.59 (12)	C11—C10—H10	120.1
O1—CU1—O1^i	78.91 (12)	C12—C11—C10	121.2 (5)
N2—CU1—O1^i	90.61 (12)	C12—C11—BR2	120.0 (4)
N1—CU1—O1^i	113.35 (13)	C10—C11—BR2	118.8 (4)
C7—N1—C15	115.8 (4)	C11—C12—C13	120.2 (5)
C7—N1—CU1	122.7 (3)	C11—C12—H12	119.9
C15—N1—CU1	121.2 (3)	C13—C12—H12	119.9
C14—N2—C17	116.0 (4)	C8—C13—C12	119.7 (4)
C14—N2—CU1	123.6 (3)	C8—C13—C14	122.2 (4)
C17—N2—CU1	120.2 (3)	C12—C13—C14	117.9 (4)
C1—O1—CU1	127.1 (3)	N2—C14—C13	127.6 (4)
C8—O2—CU1	129.2 (3)	N2—C14—H14	116.2
C16—S1—S2	103.67 (16)	C13—C14—H14	116.2
C18^ii—S2—S1	101.41 (16)	N1—C15—C16	110.9 (4)
O1—C1—C2	119.0 (4)	N1—C15—H15A	109.5
O1—C1—C6	123.5 (4)	C16—C15—H15A	109.5
C2—C1—C6	117.5 (4)	N1—C15—H15B	109.5
C3—C2—C1	121.8 (5)	C16—C15—H15B	109.5
C3—C2—H2	119.1	H15A—C15—H15B	108.0
C1—C2—H2	119.1	C15—C16—S1	113.1 (3)
C2—C3—C4	120.0 (4)	C15—C16—H16A	109.0
C2—C3—H3	120.0	S1—C16—H16A	109.0
C4—C3—H3	120.0	C15—C16—H16B	109.0
C5—C4—C3	119.9 (5)	S1—C16—H16B	109.0
C5—C4—BR1	119.9 (4)	H16A—C16—H16B	107.8
C3—C4—BR1	120.2 (4)	N2—C17—C18	113.8 (4)
C4—C5—C6	120.7 (5)	N2—C17—H17A	108.8
C4—C5—H5	119.7	C18—C17—H17A	108.8
C6—C5—H5	119.7	N2—C17—H17B	108.8
C5—C6—C1	120.1 (4)	C18—C17—H17B	108.8
C5—C6—C7	117.3 (4)	H17A—C17—H17B	107.7
C1—C6—C7	122.7 (4)	C17—C18—S2^ii	113.1 (3)
N1—C7—C6	128.2 (4)	C17—C18—H18A	109.0
N1—C7—H7	115.9	S2^ii—C18—H18A	109.0
C6—C7—H7	115.9	C17—C18—H18B	109.0
O2—C8—C13	124.2 (4)	S2^ii—C18—H18B	109.0
O2—C8—C9	118.0 (4)	H18A—C18—H18B	107.8

Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+2, −y, −z+2.