Bis[4-amino-N-(pyrimidin-2-yl-κN)benzene-sulfonamidato-κN](4,4'-di-methyl-2,2'-bipyridine-κN,N')cadmium dimethyl-formamide disolvate.

In the title compound, [Cd(C(10)H(9)N(4)O(2)S)(2)(C(12)H(12)N(2))]·2C(3)H(7)NO, the Cd(II) ion lies on a twofold rotation axis, is six-coordinated by N atoms, and displays a trigonal-prismatic geometry arising from the two sulfadiazinate ligands and one 4,4'-dimethyl-2,2'-bipyridine ligand. Both ligands are bidentate and coordinate via their N atoms. The O and carbonyl C atoms of the dimethyl-formamide mol-ecule show disorder and were modelled with two different orientations and with site occupancies of 0.584 (10):0.416 (10). The geometry around the sulfadiazine S atom is distorted tetra-hedral. The crystal structure involves N-H⋯O hydrogen bonds which link mol-ecules into a three-dimensional network. Weak C-H⋯O hydrogen bonds are also observed.

Related literature

For the comparison of the N—H bond distance of the terminal amine group and the C—S—N—C torsion angle, see: Heren et al. (2006 ▶); Hossain & Amoroso (2007 ▶); Hossain (2011 ▶). For the hydrogen bonds of sulfadiazinate anions, see: Paşaoğlu et al. (2008 ▶). For the comparison of the dihedral angle between the aromatic rings of the anion, see: Hossain & Amoroso (2007 ▶); Hossain (2011 ▶). For the comparison of Cd—N bond distances, see: Kalateh et al. (2010 ▶); Hossain (2011 ▶).

Experimental

Crystal data

[Cd(C10H9N4O2S)2(C12H12N2)]·2C3H7NO

M = 941.37

Monoclinic,

a = 17.4428 (4) Å

b = 16.2753 (4) Å

c = 16.3873 (4) Å

β = 118.3334 (11)°

V = 4094.81 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.70 mm−1

T = 150 K

0.20 × 0.20 × 0.18 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.873, T max = 0.885

18995 measured reflections

4685 independent reflections

3855 reflections with I > 2σ(I)

R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.093

S = 1.04

4685 reflections

297 parameters

30 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.55 e Å−3

Δρmin = −0.59 e Å−3

Data collection: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT (Hooft, 1998 ▶); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812004412/rn2090sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004412/rn2090Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cd(C10H9N4O2S)2(C12H12N2)]·2C3H7NO	F(000) = 1936
Mr = 941.37	Dx = 1.527 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4685 reflections
a = 17.4428 (4) Å	θ = 2.9–27.5°
b = 16.2753 (4) Å	µ = 0.70 mm−1
c = 16.3873 (4) Å	T = 150 K
β = 118.3334 (11)°	Block, white
V = 4094.81 (17) Å3	0.20 × 0.20 × 0.18 mm
Z = 4

Nonius KappaCCD diffractometer	4685 independent reflections
Radiation source: fine-focus sealed tube	3855 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.070
ω scans	θmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan (Blessing, 1995)	h = −22→22
Tmin = 0.873, Tmax = 0.885	k = −20→21
18995 measured reflections	l = −21→21

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0369P)2 + 6.0396P] where P = (Fo2 + 2Fc2)/3
4685 reflections	(Δ/σ)max < 0.001
297 parameters	Δρmax = 0.55 e Å−3
30 restraints	Δρmin = −0.59 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cd1	0.5000	0.285613 (15)	0.2500	0.02672 (10)
S11	0.30729 (4)	0.17732 (4)	0.20921 (4)	0.02384 (15)
O11	0.24693 (12)	0.19449 (12)	0.24412 (14)	0.0332 (4)
O12	0.28358 (12)	0.20915 (11)	0.11776 (12)	0.0311 (4)
N11	0.40303 (13)	0.21330 (12)	0.27493 (14)	0.0242 (5)
N12	0.53497 (14)	0.21773 (13)	0.40087 (14)	0.0253 (5)
N13	0.42490 (14)	0.13244 (14)	0.40597 (14)	0.0282 (5)
N14	0.34151 (18)	−0.18335 (14)	0.19655 (18)	0.0384 (6)
C11	0.45350 (16)	0.18555 (15)	0.36375 (17)	0.0231 (5)
C12	0.59239 (18)	0.19244 (18)	0.48605 (18)	0.0330 (6)
H12	0.6500	0.2136	0.5142	0.040*
C13	0.56952 (19)	0.13622 (19)	0.53386 (19)	0.0368 (7)
H13	0.6105	0.1171	0.5936	0.044*
C14	0.48492 (19)	0.10921 (18)	0.49108 (18)	0.0331 (6)
H14	0.4677	0.0717	0.5238	0.040*
C15	0.31751 (15)	0.07013 (15)	0.20727 (16)	0.0222 (5)
C16	0.26797 (16)	0.01885 (16)	0.23138 (17)	0.0262 (5)
H16	0.2286	0.0417	0.2500	0.031*
C17	0.27577 (16)	−0.06534 (16)	0.22831 (17)	0.0268 (6)
H17	0.2412	−0.1000	0.2444	0.032*
C18	0.33400 (17)	−0.10060 (16)	0.20182 (16)	0.0264 (6)
C19	0.38526 (18)	−0.04727 (16)	0.17978 (18)	0.0290 (6)
H19	0.4262	−0.0696	0.1630	0.035*
C20	0.37690 (17)	0.03677 (16)	0.18217 (17)	0.0259 (5)
H20	0.4116	0.0719	0.1667	0.031*
N1	0.42193 (15)	0.40137 (14)	0.17391 (15)	0.0305 (5)
C1	0.45450 (17)	0.47574 (16)	0.21050 (18)	0.0266 (6)
C2	0.40492 (17)	0.54691 (16)	0.17667 (18)	0.0270 (6)
H2	0.4285	0.5985	0.2043	0.032*
C3	0.32125 (17)	0.54268 (18)	0.10280 (18)	0.0298 (6)
C4	0.29046 (19)	0.46709 (19)	0.0646 (2)	0.0375 (7)
H4	0.2341	0.4620	0.0127	0.045*
C5	0.34180 (19)	0.39805 (19)	0.1019 (2)	0.0391 (7)
H5	0.3190	0.3460	0.0750	0.047*
C6	0.26532 (18)	0.61872 (18)	0.0669 (2)	0.0358 (7)
H6A	0.2244	0.6211	0.0921	0.054*
H6B	0.2328	0.6167	−0.0010	0.054*
H6C	0.3025	0.6676	0.0863	0.054*
N2	0.52238 (17)	0.33948 (15)	0.96056 (17)	0.0372 (6)
C8	0.4460 (2)	0.3874 (3)	0.9325 (4)	0.0815 (15)
H8A	0.3993	0.3653	0.8745	0.122*
H8B	0.4580	0.4444	0.9228	0.122*
H8C	0.4280	0.3856	0.9807	0.122*
C9	0.5952 (2)	0.3585 (2)	1.0476 (2)	0.0591 (10)
H9A	0.6398	0.3159	1.0638	0.089*
H9B	0.5766	0.3610	1.0953	0.089*
H9C	0.6194	0.4118	1.0435	0.089*
C7	0.5088 (5)	0.2855 (3)	0.8943 (4)	0.0388 (16)	0.584 (10)
H7	0.4531	0.2804	0.8415	0.047*	0.584 (10)
O1	0.5723 (3)	0.2409 (3)	0.9032 (3)	0.0543 (17)	0.584 (10)
C7D	0.5528 (7)	0.2831 (6)	0.9201 (7)	0.049 (2)	0.416 (10)
H7'	0.6071	0.2589	0.9614	0.058*	0.416 (10)
O1D	0.5248 (4)	0.2615 (4)	0.8480 (5)	0.054 (3)	0.416 (10)
H14A	0.3127 (18)	−0.2243 (13)	0.213 (2)	0.044 (9)*
H14B	0.3791 (19)	−0.2145 (17)	0.182 (3)	0.060 (11)*

	U11	U22	U33	U12	U13	U23
Cd1	0.02882 (16)	0.01675 (15)	0.03504 (16)	0.000	0.01553 (12)	0.000
S11	0.0178 (3)	0.0207 (3)	0.0262 (3)	0.0004 (2)	0.0049 (2)	−0.0001 (2)
O11	0.0238 (9)	0.0312 (10)	0.0451 (11)	0.0031 (8)	0.0167 (8)	−0.0055 (9)
O12	0.0249 (9)	0.0288 (10)	0.0266 (9)	0.0017 (8)	0.0016 (7)	0.0067 (8)
N11	0.0202 (10)	0.0206 (11)	0.0244 (10)	−0.0030 (8)	0.0047 (8)	−0.0018 (9)
N12	0.0205 (10)	0.0239 (11)	0.0252 (10)	−0.0010 (9)	0.0057 (8)	−0.0039 (9)
N13	0.0298 (11)	0.0270 (12)	0.0243 (11)	−0.0017 (9)	0.0101 (9)	−0.0010 (9)
N14	0.0512 (16)	0.0190 (12)	0.0487 (15)	−0.0013 (11)	0.0268 (13)	0.0009 (11)
C11	0.0221 (12)	0.0189 (12)	0.0240 (12)	0.0014 (10)	0.0074 (10)	−0.0032 (10)
C12	0.0257 (13)	0.0362 (16)	0.0269 (13)	0.0034 (12)	0.0043 (11)	−0.0045 (12)
C13	0.0341 (15)	0.0438 (17)	0.0228 (13)	0.0078 (13)	0.0057 (11)	0.0012 (12)
C14	0.0428 (16)	0.0298 (15)	0.0280 (13)	0.0024 (13)	0.0179 (12)	0.0028 (12)
C15	0.0188 (12)	0.0200 (12)	0.0222 (11)	−0.0014 (9)	0.0050 (9)	−0.0004 (10)
C16	0.0197 (12)	0.0293 (14)	0.0265 (12)	−0.0015 (10)	0.0085 (10)	0.0000 (11)
C17	0.0231 (13)	0.0280 (14)	0.0255 (12)	−0.0051 (11)	0.0084 (10)	0.0032 (11)
C18	0.0300 (14)	0.0233 (13)	0.0199 (11)	−0.0032 (11)	0.0068 (10)	0.0011 (10)
C19	0.0341 (15)	0.0267 (14)	0.0309 (13)	0.0002 (12)	0.0191 (12)	−0.0018 (11)
C20	0.0282 (13)	0.0241 (13)	0.0286 (13)	−0.0048 (11)	0.0159 (11)	−0.0008 (11)
N1	0.0304 (12)	0.0213 (11)	0.0362 (12)	−0.0023 (9)	0.0128 (10)	−0.0008 (10)
C1	0.0267 (14)	0.0255 (13)	0.0290 (13)	−0.0021 (11)	0.0143 (11)	−0.0015 (11)
C2	0.0315 (14)	0.0211 (13)	0.0296 (13)	−0.0046 (11)	0.0154 (11)	−0.0025 (11)
C3	0.0259 (13)	0.0370 (16)	0.0270 (13)	0.0012 (12)	0.0129 (11)	0.0004 (12)
C4	0.0290 (15)	0.0374 (17)	0.0379 (16)	−0.0034 (13)	0.0092 (12)	0.0008 (13)
C5	0.0338 (16)	0.0275 (15)	0.0447 (16)	−0.0060 (12)	0.0095 (13)	−0.0008 (13)
C6	0.0289 (14)	0.0339 (16)	0.0377 (15)	0.0005 (12)	0.0103 (12)	−0.0018 (13)
N2	0.0423 (14)	0.0328 (13)	0.0374 (13)	−0.0080 (11)	0.0195 (11)	−0.0039 (11)
C8	0.041 (2)	0.056 (3)	0.106 (4)	−0.0036 (19)	0.002 (2)	0.013 (2)
C9	0.0377 (18)	0.059 (2)	0.054 (2)	−0.0155 (17)	0.0009 (16)	0.0119 (18)
C7	0.0388 (18)	0.0393 (18)	0.0386 (18)	−0.0027 (10)	0.0186 (11)	0.0007 (10)
O1	0.0560 (19)	0.0551 (19)	0.0553 (19)	0.0001 (10)	0.0294 (12)	−0.0005 (9)
C7D	0.049 (3)	0.048 (3)	0.049 (3)	0.0000 (10)	0.0236 (14)	0.0008 (10)
O1D	0.055 (3)	0.055 (3)	0.055 (3)	−0.0006 (10)	0.0273 (15)	−0.0027 (10)

Cd1—N1	2.312 (2)	C19—H19	0.9500
Cd1—N11	2.251 (2)	C20—H20	0.9500
Cd1—N11i	2.251 (2)	N1—C5	1.336 (4)
Cd1—N1i	2.312 (2)	N1—C1	1.350 (3)
Cd1—N12i	2.505 (2)	C1—C2	1.394 (4)
Cd1—N12	2.505 (2)	C1—C1i	1.498 (5)
S11—O11	1.444 (2)	C2—C3	1.387 (4)
S11—O12	1.448 (2)	C2—H2	0.9500
S11—N11	1.608 (2)	C3—C4	1.369 (4)
S11—C15	1.755 (3)	C3—C6	1.512 (4)
N11—C11	1.372 (3)	C4—C5	1.385 (4)
N12—C12	1.339 (3)	C4—H4	0.9500
N12—C11	1.358 (3)	C5—H5	0.9500
N13—C14	1.341 (3)	C6—H6A	0.9800
N13—C11	1.342 (3)	C6—H6B	0.9800
N14—C18	1.360 (3)	C6—H6C	0.9800
N14—H14A	0.948 (3)	N2—C7	1.328 (6)
N14—H14B	0.948 (3)	N2—C7D	1.377 (9)
C12—C13	1.381 (4)	N2—C8	1.418 (5)
C12—H12	0.9500	N2—C9	1.422 (4)
C13—C14	1.371 (4)	C8—H8A	0.9800
C13—H13	0.9500	C8—H8B	0.9800
C14—H14	0.9500	C8—H8C	0.9800
C15—C16	1.387 (4)	C9—H9A	0.9800
C15—C20	1.393 (4)	C9—H9B	0.9800
C16—C17	1.380 (4)	C9—H9C	0.9800
C16—H16	0.9500	C7—O1	1.274 (9)
C17—C18	1.403 (4)	C7—H7	0.9500
C17—H17	0.9500	C7D—O1D	1.101 (11)
C18—C19	1.411 (4)	C7D—H7'	0.9500
C19—C20	1.378 (4)
N11i—Cd1—N11	116.97 (11)	C20—C19—C18	121.0 (2)
N11i—Cd1—N1i	102.88 (8)	C20—C19—H19	119.5
N11—Cd1—N1i	128.97 (8)	C18—C19—H19	119.5
N11i—Cd1—N1	128.97 (8)	C19—C20—C15	119.9 (2)
N11—Cd1—N1	102.88 (8)	C19—C20—H20	120.0
N1i—Cd1—N1	70.87 (11)	C15—C20—H20	120.0
N11i—Cd1—N12i	56.10 (7)	C5—N1—C1	118.2 (2)
N11—Cd1—N12i	95.54 (7)	C5—N1—Cd1	123.03 (19)
N1i—Cd1—N12i	134.18 (8)	C1—N1—Cd1	118.35 (17)
N1—Cd1—N12i	91.26 (7)	N1—C1—C2	121.2 (2)
N11i—Cd1—N12	95.54 (7)	N1—C1—C1i	115.69 (15)
N11—Cd1—N12	56.10 (7)	C2—C1—C1i	123.14 (15)
N1i—Cd1—N12	91.26 (7)	C3—C2—C1	120.2 (2)
N1—Cd1—N12	134.18 (8)	C3—C2—H2	119.9
N12i—Cd1—N12	127.65 (9)	C1—C2—H2	119.9
O11—S11—O12	115.91 (12)	C4—C3—C2	117.8 (3)
O11—S11—N11	112.65 (12)	C4—C3—C6	121.1 (2)
O12—S11—N11	104.99 (11)	C2—C3—C6	121.1 (3)
O11—S11—C15	107.39 (12)	C3—C4—C5	119.7 (3)
O12—S11—C15	108.56 (11)	C3—C4—H4	120.1
N11—S11—C15	106.97 (11)	C5—C4—H4	120.1
C11—N11—S11	122.04 (18)	N1—C5—C4	122.9 (3)
C11—N11—Cd1	101.86 (15)	N1—C5—H5	118.5
S11—N11—Cd1	134.42 (12)	C4—C5—H5	118.5
C12—N12—C11	117.0 (2)	C3—C6—H6A	109.5
C12—N12—Cd1	151.11 (19)	C3—C6—H6B	109.5
C11—N12—Cd1	90.87 (14)	H6A—C6—H6B	109.5
C14—N13—C11	114.8 (2)	C3—C6—H6C	109.5
C18—N14—H14A	126.8 (19)	H6A—C6—H6C	109.5
C18—N14—H14B	130 (2)	H6B—C6—H6C	109.5
H14A—N14—H14B	103 (2)	C7—N2—C7D	29.0 (4)
N13—C11—N12	125.7 (2)	C7—N2—C8	108.8 (4)
N13—C11—N11	123.4 (2)	C7D—N2—C8	136.6 (5)
N12—C11—N11	110.9 (2)	C7—N2—C9	133.8 (4)
N12—C12—C13	121.4 (3)	C7D—N2—C9	105.2 (5)
N12—C12—H12	119.3	C8—N2—C9	117.4 (3)
C13—C12—H12	119.3	N2—C8—H8A	109.5
C14—C13—C12	116.9 (2)	N2—C8—H8B	109.5
C14—C13—H13	121.5	H8A—C8—H8B	109.5
C12—C13—H13	121.5	N2—C8—H8C	109.5
N13—C14—C13	124.1 (3)	H8A—C8—H8C	109.5
N13—C14—H14	117.9	H8B—C8—H8C	109.5
C13—C14—H14	117.9	N2—C9—H9A	109.5
C16—C15—C20	120.0 (2)	N2—C9—H9B	109.5
C16—C15—S11	120.7 (2)	H9A—C9—H9B	109.5
C20—C15—S11	119.26 (19)	N2—C9—H9C	109.5
C17—C16—C15	120.1 (2)	H9A—C9—H9C	109.5
C17—C16—H16	119.9	H9B—C9—H9C	109.5
C15—C16—H16	119.9	O1—C7—N2	118.4 (6)
C16—C17—C18	121.0 (2)	O1—C7—H7	120.8
C16—C17—H17	119.5	N2—C7—H7	120.8
C18—C17—H17	119.5	O1D—C7D—N2	130.8 (10)
N14—C18—C17	122.0 (2)	O1D—C7D—H7'	114.6
N14—C18—C19	120.1 (3)	N2—C7D—H7'	114.6
C17—C18—C19	117.9 (2)
O11—S11—N11—C11	64.3 (2)	N11—S11—C15—C16	124.8 (2)
O12—S11—N11—C11	−168.7 (2)	O11—S11—C15—C20	−175.67 (19)
C15—S11—N11—C11	−53.5 (2)	O12—S11—C15—C20	58.3 (2)
O11—S11—N11—Cd1	−133.41 (16)	N11—S11—C15—C20	−54.5 (2)
O12—S11—N11—Cd1	−6.41 (19)	C20—C15—C16—C17	−1.6 (4)
C15—S11—N11—Cd1	108.82 (17)	S11—C15—C16—C17	179.10 (19)
N11i—Cd1—N11—C11	74.58 (14)	C15—C16—C17—C18	0.6 (4)
N1i—Cd1—N11—C11	−62.58 (18)	C16—C17—C18—N14	−178.7 (2)
N1—Cd1—N11—C11	−138.26 (15)	C16—C17—C18—C19	0.9 (4)
N12i—Cd1—N11—C11	129.18 (15)	N14—C18—C19—C20	178.2 (2)
N12—Cd1—N11—C11	−3.22 (13)	C17—C18—C19—C20	−1.5 (4)
N11i—Cd1—N11—S11	−90.16 (16)	C18—C19—C20—C15	0.4 (4)
N1i—Cd1—N11—S11	132.68 (15)	C16—C15—C20—C19	1.1 (4)
N1—Cd1—N11—S11	57.01 (18)	S11—C15—C20—C19	−179.6 (2)
N12i—Cd1—N11—S11	−35.56 (17)	N11i—Cd1—N1—C5	93.2 (2)
N12—Cd1—N11—S11	−168.0 (2)	N11—Cd1—N1—C5	−48.3 (2)
N11i—Cd1—N12—C12	49.8 (4)	N1i—Cd1—N1—C5	−175.5 (3)
N11—Cd1—N12—C12	168.7 (4)	N12i—Cd1—N1—C5	47.6 (2)
N1i—Cd1—N12—C12	−53.3 (4)	N12—Cd1—N1—C5	−103.2 (2)
N1—Cd1—N12—C12	−117.5 (4)	N11i—Cd1—N1—C1	−94.7 (2)
N12i—Cd1—N12—C12	100.5 (4)	N11—Cd1—N1—C1	123.7 (2)
N11i—Cd1—N12—C11	−115.75 (15)	N1i—Cd1—N1—C1	−3.43 (14)
N11—Cd1—N12—C11	3.18 (13)	N12i—Cd1—N1—C1	−140.3 (2)
N1i—Cd1—N12—C11	141.18 (15)	N12—Cd1—N1—C1	68.8 (2)
N1—Cd1—N12—C11	77.01 (17)	C5—N1—C1—C2	2.5 (4)
N12i—Cd1—N12—C11	−65.01 (13)	Cd1—N1—C1—C2	−169.96 (19)
C14—N13—C11—N12	−1.9 (4)	C5—N1—C1—C1i	−178.4 (3)
C14—N13—C11—N11	176.8 (2)	Cd1—N1—C1—C1i	9.1 (4)
C12—N12—C11—N13	2.0 (4)	N1—C1—C2—C3	−1.5 (4)
Cd1—N12—C11—N13	174.2 (2)	C1i—C1—C2—C3	179.5 (3)
C12—N12—C11—N11	−176.8 (2)	C1—C2—C3—C4	−0.8 (4)
Cd1—N12—C11—N11	−4.64 (19)	C1—C2—C3—C6	178.1 (2)
S11—N11—C11—N13	−6.4 (3)	C2—C3—C4—C5	1.9 (4)
Cd1—N11—C11—N13	−173.6 (2)	C6—C3—C4—C5	−177.0 (3)
S11—N11—C11—N12	172.46 (17)	C1—N1—C5—C4	−1.3 (5)
Cd1—N11—C11—N12	5.3 (2)	Cd1—N1—C5—C4	170.8 (2)
C11—N12—C12—C13	−0.1 (4)	C3—C4—C5—N1	−1.0 (5)
Cd1—N12—C12—C13	−163.8 (3)	C7D—N2—C7—O1	8.8 (9)
N12—C12—C13—C14	−1.6 (4)	C8—N2—C7—O1	174.5 (5)
C11—N13—C14—C13	−0.1 (4)	C9—N2—C7—O1	−3.4 (8)
C12—C13—C14—N13	1.7 (4)	C7—N2—C7D—O1D	24.3 (8)
O11—S11—C15—C16	3.6 (2)	C8—N2—C7D—O1D	4.4 (16)
O12—S11—C15—C16	−122.4 (2)	C9—N2—C7D—O1D	−164.8 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N14—H14B···O1Dii	0.95 (1)	2.10 (1)	3.034 (7)	169 (3)
N14—H14B···O1ii	0.95 (1)	1.99 (2)	2.853 (5)	151 (3)
N14—H14A···O11iii	0.95 (1)	2.00 (1)	2.950 (3)	176 (3)
C12—H12···O12iv	0.95	2.48	3.393 (3)	162
C6—H6C···O1v	0.98	2.58	3.487 (5)	154
C6—H6A···N13vi	0.98	2.63	3.558 (4)	159
C8—H8A···O11vii	0.98	2.55	3.497 (4)	161

Cd1—N1	2.312 (2)
Cd1—N11	2.251 (2)
Cd1—N12	2.505 (2)
N14—C18	1.360 (3)

N11i—Cd1—N11	116.97 (11)
N11—Cd1—N1i	128.97 (8)
N11—Cd1—N1	102.88 (8)
N1i—Cd1—N1	70.87 (11)
N11—Cd1—N12i	95.54 (7)
N1—Cd1—N12i	91.26 (7)
N11—Cd1—N12	56.10 (7)
N1—Cd1—N12	134.18 (8)
N12i—Cd1—N12	127.65 (9)
N13—C11—N12	125.7 (2)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N14—H14B⋯O1Dii	0.95 (1)	2.10 (1)	3.034 (7)	169 (3)
N14—H14B⋯O1ii	0.95 (1)	1.99 (2)	2.853 (5)	151 (3)
N14—H14A⋯O11iii	0.95 (1)	2.00 (1)	2.950 (3)	176 (3)
C12—H12⋯O12iv	0.95	2.48	3.393 (3)	162
C6—H6C⋯O1v	0.98	2.58	3.487 (5)	154
C6—H6A⋯N13vi	0.98	2.63	3.558 (4)	159
C8—H8A⋯O11vii	0.98	2.55	3.497 (4)	161

Symmetry codes: (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .