Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The mechanisms of inter­action of inorganic complexes with DNA are important in the design and development of new metal-based drug mol­ecules. The limitations of cis-platin have encouraged the design and development of new metal-based target-specific anti­cancer drugs having reduced side effects. The com­plex cis-di­chlorido­bis­(1,2,5-thia­diazolo[3,4-f][1,10]phenanthroline-κ2N1,N10)copper(II), [CuCl2(C12H6N4S)2], has been synthesized and characterized. The complex crystallizes in the monoclinic space group C2/c. The covalent binding of the complex with DNA was studied by absorption spectroscopy. The anti­cancer activity of the complex on the Human Lung Carcinoma (A549) cell line was investigated by MTT assay. The complex exhibits higher toxicity than cis-platin and induces an apoptotic mode of cell death.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617018551/fp3044sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617018551/fp3044Isup2.hkl
Contains datablock I

CCDC reference: 1563768

Computing details top

Data collection: SMART (Bruker, 2014); cell refinement: SMART (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

cis-Dichloridobis(1,2,5-thiadiazolo[3,4-f][1,10]phenanthroline-κ2N1,N10)copper(II) top
Crystal data top
[CuCl2(C12H6N4S)2]F(000) = 1228
Mr = 610.98Dx = 1.775 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 8.181 (4) ÅCell parameters from 4383 reflections
b = 12.168 (5) Åθ = 3.0–25.7°
c = 22.99 (1) ŵ = 1.41 mm1
β = 92.197 (7)°T = 298 K
V = 2286.8 (17) Å3Plate, blue
Z = 40.28 × 0.24 × 0.16 mm
Data collection top
Bruker SMART CCD area detector
diffractometer
1974 reflections with I > 2σ(I)
phi and ω scansRint = 0.033
Absorption correction: empirical (using intensity measurements)
sadabs
θmax = 26.1°, θmin = 1.8°
Tmin = 0.694, Tmax = 0.806h = 1010
11562 measured reflectionsk = 1414
2250 independent reflectionsl = 2828
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.116 w = 1/[σ2(Fo2) + (0.059P)2 + 4.722P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
2250 reflectionsΔρmax = 0.59 e Å3
168 parametersΔρmin = 0.60 e Å3
0 restraints
Special details top

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 (Å2) top
xyzUiso*/Ueq
Cu10.50000.57810 (5)0.75000.0462 (2)
Cl10.66036 (11)0.72346 (9)0.80884 (4)0.0685 (3)
S10.66218 (14)0.34721 (8)0.45450 (4)0.0648 (3)
N10.6788 (3)0.5646 (2)0.69073 (10)0.0417 (6)
N20.3942 (3)0.4572 (2)0.68896 (12)0.0530 (7)
N30.7753 (4)0.4210 (2)0.49855 (11)0.0518 (7)
N40.5045 (4)0.3292 (2)0.49399 (13)0.0588 (7)
C50.6413 (3)0.5034 (2)0.64287 (12)0.0362 (6)
C40.7471 (3)0.4960 (2)0.59694 (12)0.0372 (6)
C110.6915 (4)0.4333 (2)0.54656 (12)0.0400 (6)
C60.4837 (3)0.4471 (2)0.64110 (13)0.0391 (6)
C30.8977 (4)0.5490 (3)0.60191 (13)0.0454 (7)
H30.97070.54490.57200.054*
C70.4298 (4)0.3880 (2)0.59198 (14)0.0441 (7)
C120.5365 (4)0.3814 (2)0.54411 (13)0.0446 (7)
C10.8235 (4)0.6141 (3)0.69432 (13)0.0484 (7)
H10.85000.65560.72730.058*
C20.9369 (4)0.6071 (3)0.65127 (14)0.0508 (8)
H21.03820.64140.65590.061*
C80.2742 (4)0.3401 (3)0.5925 (2)0.0632 (10)
H80.23230.30200.56030.076*
C100.2498 (5)0.4079 (3)0.6886 (2)0.0701 (12)
H100.18860.41220.72180.084*
C90.1856 (4)0.3503 (3)0.6409 (2)0.0759 (13)
H90.08220.31880.64210.091*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0457 (3)0.0633 (4)0.0304 (3)0.0000.0113 (2)0.000
Cl10.0583 (5)0.0901 (7)0.0585 (5)0.0259 (5)0.0216 (4)0.0145 (5)
S10.0986 (8)0.0612 (6)0.0344 (4)0.0161 (5)0.0014 (4)0.0080 (4)
N10.0422 (13)0.0533 (14)0.0300 (12)0.0028 (11)0.0043 (10)0.0009 (10)
N20.0418 (14)0.0692 (18)0.0493 (16)0.0116 (13)0.0177 (12)0.0173 (13)
N30.0660 (18)0.0557 (16)0.0345 (13)0.0086 (13)0.0153 (12)0.0011 (11)
N40.0701 (19)0.0513 (16)0.0538 (16)0.0059 (14)0.0147 (14)0.0089 (13)
C50.0359 (14)0.0429 (15)0.0301 (13)0.0053 (11)0.0051 (10)0.0030 (11)
C40.0362 (14)0.0425 (15)0.0331 (14)0.0039 (11)0.0061 (11)0.0031 (11)
C110.0446 (16)0.0428 (15)0.0329 (14)0.0064 (12)0.0050 (12)0.0024 (11)
C60.0334 (14)0.0443 (15)0.0400 (15)0.0052 (11)0.0079 (11)0.0077 (12)
C30.0359 (15)0.0567 (18)0.0444 (17)0.0031 (13)0.0116 (12)0.0035 (13)
C70.0365 (15)0.0390 (15)0.0568 (18)0.0014 (12)0.0008 (13)0.0071 (13)
C120.0499 (17)0.0393 (15)0.0442 (16)0.0050 (13)0.0046 (13)0.0002 (13)
C10.0472 (17)0.0589 (19)0.0388 (16)0.0002 (14)0.0021 (13)0.0054 (14)
C20.0375 (16)0.0615 (19)0.0532 (19)0.0056 (14)0.0004 (14)0.0007 (16)
C80.0439 (18)0.0489 (19)0.096 (3)0.0049 (15)0.0023 (18)0.0049 (19)
C100.048 (2)0.077 (3)0.088 (3)0.0127 (18)0.032 (2)0.032 (2)
C90.0360 (18)0.061 (2)0.131 (4)0.0055 (16)0.015 (2)0.024 (2)
Geometric parameters (Å, º) top
Cu1—Cl12.5579 (14)C4—C111.446 (4)
Cu1—Cl1i2.5579 (14)C4—C31.391 (4)
Cu1—N12.043 (2)C11—C121.415 (4)
Cu1—N1i2.043 (2)C6—C71.396 (4)
Cu1—N22.189 (3)C3—H30.9300
Cu1—N2i2.189 (3)C3—C21.365 (4)
S1—N31.617 (3)C7—C121.433 (4)
S1—N41.620 (4)C7—C81.401 (4)
N1—C51.354 (4)C1—H10.9300
N1—C11.329 (4)C1—C21.385 (4)
N2—C61.350 (4)C2—H20.9300
N2—C101.324 (5)C8—H80.9300
N3—C111.330 (4)C8—C91.356 (6)
N4—C121.333 (4)C10—H100.9300
C5—C41.394 (4)C10—C91.387 (6)
C5—C61.460 (4)C9—H90.9300
Cl1i—Cu1—Cl192.51 (6)N3—C11—C4124.6 (3)
N1i—Cu1—Cl193.93 (8)N3—C11—C12114.0 (3)
N1—Cu1—Cl1i93.93 (8)C12—C11—C4121.4 (3)
N1—Cu1—Cl192.44 (8)N2—C6—C5116.1 (3)
N1i—Cu1—Cl1i92.44 (8)N2—C6—C7122.8 (3)
N1—Cu1—N1i170.78 (15)C7—C6—C5121.0 (3)
N1i—Cu1—N295.62 (10)C4—C3—H3120.4
N1—Cu1—N2i95.62 (10)C2—C3—C4119.2 (3)
N1—Cu1—N278.11 (10)C2—C3—H3120.4
N1i—Cu1—N2i78.11 (10)C6—C7—C12117.9 (3)
N2—Cu1—Cl1170.44 (7)C6—C7—C8117.7 (3)
N2—Cu1—Cl1i86.76 (8)C8—C7—C12124.4 (3)
N2i—Cu1—Cl1i170.44 (7)N4—C12—C11113.1 (3)
N2i—Cu1—Cl186.76 (8)N4—C12—C7125.8 (3)
N2—Cu1—N2i95.52 (15)C11—C12—C7121.0 (3)
N3—S1—N499.95 (14)N1—C1—H1118.4
C5—N1—Cu1116.15 (19)N1—C1—C2123.2 (3)
C1—N1—Cu1125.5 (2)C2—C1—H1118.4
C1—N1—C5118.3 (3)C3—C2—C1118.9 (3)
C6—N2—Cu1111.7 (2)C3—C2—H2120.5
C10—N2—Cu1129.8 (3)C1—C2—H2120.5
C10—N2—C6117.7 (3)C7—C8—H8120.5
C11—N3—S1106.3 (2)C9—C8—C7119.0 (4)
C12—N4—S1106.6 (2)C9—C8—H8120.5
N1—C5—C4121.6 (3)N2—C10—H10118.5
N1—C5—C6116.9 (2)N2—C10—C9123.0 (4)
C4—C5—C6121.5 (3)C9—C10—H10118.5
C5—C4—C11117.1 (3)C8—C9—C10119.7 (3)
C3—C4—C5118.8 (3)C8—C9—H9120.1
C3—C4—C11124.1 (3)C10—C9—H9120.1
Symmetry code: (i) x+1, y, z+3/2.
 

Subscribe to Acta Crystallographica Section C: Structural Chemistry

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds