Aqua-(4,5-dihydroxy-benzene-1,3-disulfonato-κO)bis-(1,10-phenanthroline-κN,N')cadmium(II) monohydrate.

In the title compound, [Cd(C(6)H(4)O(8)S(2))(C(12)H(8)N(2))(2)(H(2)O)]·H(2)O, each Cd(II) ion is coordinated by four N atoms [Cd-N = 2.310 (7)-2.341 (7) Å] from two 1,10-phenanthroline ligands, one O atom [Cd-O = 2.300 (6) Å] from a 4,5-dihydroxy-benzene-1,3-disulfonate ligand and one aqua O atom [Cd-O = 2.288 (7) Å] in a distorted octa-hedral geometry. The crystal packing exhibits inter-molecular O-H⋯O and C-H⋯O hydrogen bonds and π-π inter-actions evidenced by relatively short distances [3.525 (5)-3.937 (6) Å] between the centroids of the six-membered rings of neighbouring mol-ecules.

Related literature

For related literature, see: Haddad & Raymond (1986 ▶); Riley et al. (1983 ▶); Sheriff et al. (2003 ▶); Sun et al. (1995 ▶).

Experimental

Crystal data

[Cd(C6H4O8S2)(C12H8N2)2(H2O)]·H2O

M = 777.05

Monoclinic,

a = 16.570 (5) Å

b = 9.330 (3) Å

c = 24.585 (6) Å

β = 127.199 (16)°

V = 3027.5 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.93 mm−1

T = 293 (2) K

0.30 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.816, T max = 0.851

6494 measured reflections

5155 independent reflections

3318 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.223

S = 1.16

5155 reflections

426 parameters

H-atom parameters constrained

Δρmax = 1.32 e Å−3

Δρmin = −2.31 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a ▶); molecular graphics: SHELXTL (Sheldrick, 1997b ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807067918/cv2375sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807067918/cv2375Isup2.hkl

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

[Cd(C6H4O8S2)(C12H8N2)2(H2O)]·H2O	F000 = 1568
Mr = 777.05	Dx = 1.705 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 672 reflections
a = 16.570 (5) Å	θ = 2.4–22.8º
b = 9.330 (3) Å	µ = 0.93 mm−1
c = 24.585 (6) Å	T = 293 (2) K
β = 127.199 (16)º	Block, colourless
V = 3027.5 (15) Å3	0.30 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	5155 independent reflections
Radiation source: fine-focus sealed tube	3318 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.031
T = 293(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.5º
Absorption correction: multi-scan(SADABS; Bruker, 2001)	h = −1→19
Tmin = 0.816, Tmax = 0.851	k = −11→1
6494 measured reflections	l = −29→24

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.067	H-atom parameters constrained
wR(F2) = 0.223	w = 1/[σ2(Fo2) + (0.084P)2 + 19.1074P] where P = (Fo2 + 2Fc2)/3
S = 1.16	(Δ/σ)max < 0.001
5155 reflections	Δρmax = 1.32 e Å−3
426 parameters	Δρmin = −2.31 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
Cd1	0.78090 (4)	0.74745 (7)	0.54487 (3)	0.0437 (2)
S1	0.87188 (16)	0.4361 (3)	0.64067 (11)	0.0466 (5)
S2	0.59688 (16)	0.4432 (3)	0.69352 (12)	0.0534 (6)
O1	0.6654 (5)	0.5671 (8)	0.4872 (4)	0.090 (3)
H1A	0.6817	0.4823	0.4953	0.135*
H1B	0.6063	0.5669	0.4528	0.135*
O2	0.8517 (5)	0.5903 (7)	0.6349 (3)	0.0574 (17)
O3	0.8155 (5)	0.3681 (8)	0.5744 (3)	0.0665 (19)
O4	0.9804 (5)	0.4051 (8)	0.6832 (4)	0.0633 (19)
O5	0.5308 (5)	0.4812 (11)	0.6236 (4)	0.084 (3)
O6	0.6305 (7)	0.5630 (14)	0.7383 (6)	0.149 (6)
O7	0.5553 (7)	0.3294 (12)	0.7104 (6)	0.123 (4)
O8	0.7292 (6)	0.1973 (10)	0.7903 (4)	0.072 (2)
H8	0.6746	0.2320	0.7770	0.108*
O9	0.8930 (5)	0.0926 (8)	0.8130 (3)	0.0590 (18)
H9	0.9284	0.0469	0.8062	0.088*
N1	0.6745 (5)	0.9283 (9)	0.4689 (4)	0.0518 (19)
N2	0.7183 (5)	0.8708 (9)	0.5940 (4)	0.0498 (18)
N3	0.9266 (5)	0.8882 (9)	0.5947 (3)	0.0489 (18)
N4	0.8570 (5)	0.6863 (9)	0.4945 (4)	0.0472 (17)
C1	0.6530 (7)	0.9512 (13)	0.4087 (5)	0.064 (3)
H1	0.6733	0.8847	0.3910	0.077*
C2	0.6005 (8)	1.0726 (15)	0.3710 (6)	0.076 (3)
H2	0.5879	1.0885	0.3292	0.092*
C3	0.5669 (8)	1.1702 (14)	0.3957 (6)	0.072 (3)
H3	0.5320	1.2520	0.3707	0.086*
C4	0.5858 (7)	1.1449 (11)	0.4582 (5)	0.057 (2)
C5	0.6410 (6)	1.0214 (10)	0.4939 (5)	0.049 (2)
C6	0.6605 (6)	0.9861 (10)	0.5582 (5)	0.048 (2)
C7	0.5465 (8)	1.2313 (11)	0.4849 (7)	0.066 (3)
H7	0.5101	1.3136	0.4614	0.079*
C8	0.5600 (7)	1.1980 (13)	0.5419 (6)	0.069 (3)
H8A	0.5327	1.2569	0.5576	0.082*
C9	0.6166 (7)	1.0715 (11)	0.5808 (5)	0.054 (2)
C10	0.6308 (8)	1.0324 (13)	0.6411 (6)	0.067 (3)
H10	0.6020	1.0862	0.6572	0.080*
C11	0.6879 (8)	0.9133 (14)	0.6760 (6)	0.066 (3)
H11	0.6971	0.8839	0.7155	0.080*
C12	0.7314 (8)	0.8380 (12)	0.6515 (5)	0.062 (3)
H12	0.7722	0.7598	0.6766	0.074*
C13	0.9588 (7)	0.9896 (11)	0.6411 (5)	0.057 (2)
H13	0.9199	1.0091	0.6559	0.069*
C14	1.0458 (8)	1.0686 (12)	0.6690 (5)	0.071 (3)
H14	1.0646	1.1392	0.7014	0.086*
C15	1.1042 (7)	1.0399 (12)	0.6476 (6)	0.071 (3)
H15	1.1638	1.0905	0.6656	0.085*
C16	1.0720 (7)	0.9326 (12)	0.5979 (5)	0.062 (3)
C17	0.9822 (6)	0.8634 (9)	0.5726 (4)	0.0409 (19)
C18	0.9451 (6)	0.7565 (9)	0.5191 (4)	0.045 (2)
C19	1.1266 (7)	0.9027 (14)	0.5705 (6)	0.072 (3)
H19	1.1869	0.9505	0.5878	0.087*
C20	1.0910 (9)	0.8066 (17)	0.5204 (7)	0.080 (4)
H20	1.1272	0.7883	0.5035	0.096*
C21	0.9986 (8)	0.7317 (11)	0.4924 (5)	0.058 (3)
C22	0.9556 (9)	0.6364 (14)	0.4378 (6)	0.074 (4)
H22	0.9876	0.6206	0.4177	0.089*
C23	0.8671 (10)	0.5656 (12)	0.4130 (6)	0.069 (3)
H23	0.8398	0.4996	0.3776	0.083*
C24	0.8199 (8)	0.5964 (11)	0.4429 (5)	0.060 (3)
H24	0.7587	0.5512	0.4257	0.072*
C25	0.7074 (5)	0.3669 (9)	0.7078 (4)	0.0366 (17)
C26	0.7595 (6)	0.2558 (9)	0.7554 (4)	0.0394 (18)
C27	0.8460 (6)	0.1997 (10)	0.7667 (4)	0.044 (2)
C28	0.8808 (6)	0.2563 (9)	0.7321 (4)	0.0389 (18)
H28	0.9399	0.2209	0.7405	0.047*
C29	0.8279 (6)	0.3649 (9)	0.6853 (4)	0.0371 (18)
C30	0.7408 (6)	0.4223 (10)	0.6727 (4)	0.0425 (19)
H30	0.7059	0.4963	0.6414	0.051*
O10	0.3768 (9)	0.3091 (18)	0.7042 (7)	0.171 (6)
H10A	0.4004	0.2821	0.7429	0.257*
H10B	0.4159	0.2782	0.6971	0.257*

	U11	U22	U33	U12	U13	U23
Cd1	0.0384 (4)	0.0485 (4)	0.0461 (4)	0.0018 (3)	0.0264 (3)	0.0014 (3)
S1	0.0409 (11)	0.0553 (14)	0.0491 (12)	0.0034 (10)	0.0300 (10)	0.0058 (11)
S2	0.0349 (11)	0.0722 (17)	0.0523 (13)	0.0129 (11)	0.0259 (10)	0.0076 (12)
O1	0.054 (4)	0.060 (5)	0.088 (6)	−0.013 (4)	0.007 (4)	0.008 (4)
O2	0.055 (4)	0.063 (4)	0.054 (4)	0.008 (3)	0.033 (3)	0.008 (3)
O3	0.075 (5)	0.076 (5)	0.059 (4)	0.005 (4)	0.046 (4)	−0.004 (4)
O4	0.041 (3)	0.065 (5)	0.092 (5)	0.009 (3)	0.044 (4)	0.013 (4)
O5	0.042 (4)	0.130 (8)	0.071 (5)	0.031 (4)	0.029 (4)	0.031 (5)
O6	0.056 (5)	0.181 (12)	0.154 (9)	0.017 (6)	0.034 (6)	−0.089 (9)
O7	0.078 (6)	0.142 (9)	0.194 (11)	0.045 (6)	0.107 (7)	0.087 (9)
O8	0.062 (4)	0.098 (6)	0.073 (5)	0.017 (4)	0.050 (4)	0.029 (4)
O9	0.054 (4)	0.074 (5)	0.058 (4)	0.027 (3)	0.039 (3)	0.025 (4)
N1	0.034 (4)	0.075 (6)	0.044 (4)	0.002 (4)	0.022 (3)	0.000 (4)
N2	0.041 (4)	0.063 (5)	0.049 (4)	−0.001 (4)	0.029 (3)	−0.004 (4)
N3	0.036 (4)	0.059 (5)	0.039 (4)	−0.002 (3)	0.016 (3)	−0.001 (4)
N4	0.047 (4)	0.049 (4)	0.044 (4)	−0.003 (4)	0.027 (3)	−0.002 (4)
C1	0.051 (5)	0.087 (8)	0.063 (6)	0.002 (6)	0.038 (5)	0.005 (6)
C2	0.058 (6)	0.104 (10)	0.067 (7)	0.019 (7)	0.038 (6)	0.025 (7)
C3	0.052 (6)	0.073 (8)	0.071 (7)	0.008 (6)	0.027 (5)	0.014 (6)
C4	0.043 (5)	0.054 (6)	0.069 (6)	0.002 (4)	0.031 (5)	−0.001 (5)
C5	0.032 (4)	0.050 (6)	0.060 (5)	−0.004 (4)	0.025 (4)	−0.002 (4)
C6	0.032 (4)	0.053 (6)	0.057 (5)	−0.003 (4)	0.026 (4)	−0.001 (4)
C7	0.050 (6)	0.046 (6)	0.084 (8)	0.006 (4)	0.032 (6)	−0.009 (5)
C8	0.044 (5)	0.064 (7)	0.087 (8)	−0.005 (5)	0.034 (6)	−0.026 (6)
C9	0.040 (5)	0.059 (6)	0.057 (5)	−0.017 (4)	0.026 (4)	−0.017 (5)
C10	0.054 (6)	0.084 (8)	0.073 (7)	−0.019 (6)	0.044 (6)	−0.034 (6)
C11	0.067 (6)	0.090 (9)	0.061 (6)	−0.014 (6)	0.048 (6)	−0.017 (6)
C12	0.057 (6)	0.066 (7)	0.058 (6)	0.000 (5)	0.033 (5)	0.004 (5)
C13	0.055 (5)	0.057 (6)	0.046 (5)	−0.004 (5)	0.024 (4)	−0.011 (5)
C14	0.056 (6)	0.052 (6)	0.060 (6)	−0.007 (5)	0.011 (5)	−0.007 (5)
C15	0.039 (5)	0.061 (7)	0.069 (7)	−0.009 (5)	0.010 (5)	0.005 (6)
C16	0.034 (5)	0.070 (7)	0.057 (6)	0.014 (5)	0.016 (4)	0.017 (5)
C17	0.029 (4)	0.034 (4)	0.044 (5)	0.005 (3)	0.015 (4)	0.012 (4)
C18	0.043 (4)	0.049 (5)	0.044 (4)	0.008 (4)	0.027 (4)	0.014 (4)
C19	0.042 (5)	0.087 (9)	0.090 (8)	−0.001 (5)	0.041 (6)	0.039 (7)
C20	0.054 (6)	0.110 (10)	0.092 (9)	0.017 (7)	0.052 (7)	0.023 (8)
C21	0.058 (5)	0.068 (7)	0.061 (6)	0.018 (5)	0.043 (5)	0.032 (5)
C22	0.094 (9)	0.094 (9)	0.064 (7)	0.040 (7)	0.063 (7)	0.024 (7)
C23	0.092 (8)	0.058 (7)	0.065 (7)	0.006 (6)	0.052 (7)	0.006 (5)
C24	0.065 (6)	0.057 (6)	0.054 (6)	0.003 (5)	0.034 (5)	−0.004 (5)
C25	0.028 (4)	0.042 (5)	0.035 (4)	0.005 (3)	0.016 (3)	−0.003 (4)
C26	0.037 (4)	0.051 (5)	0.034 (4)	0.001 (4)	0.023 (3)	−0.007 (4)
C27	0.033 (4)	0.054 (5)	0.037 (4)	0.008 (4)	0.017 (4)	0.004 (4)
C28	0.031 (4)	0.047 (5)	0.040 (4)	0.010 (4)	0.021 (3)	−0.006 (4)
C29	0.032 (4)	0.044 (5)	0.032 (4)	−0.003 (3)	0.018 (3)	0.000 (4)
C30	0.033 (4)	0.051 (5)	0.039 (4)	0.007 (4)	0.020 (4)	0.007 (4)
O10	0.119 (10)	0.232 (16)	0.159 (12)	0.043 (11)	0.082 (9)	0.040 (12)

Cd1—O1	2.285 (7)	C7—H7	0.9300
Cd1—O2	2.299 (6)	C8—C9	1.450 (16)
Cd1—N4	2.310 (7)	C8—H8A	0.9300
Cd1—N2	2.319 (7)	C9—C10	1.400 (15)
Cd1—N1	2.337 (8)	C10—C11	1.372 (16)
Cd1—N3	2.341 (7)	C10—H10	0.9300
S1—O3	1.446 (7)	C11—C12	1.378 (14)
S1—O4	1.461 (6)	C11—H11	0.9300
S1—O2	1.464 (7)	C12—H12	0.9300
S1—C29	1.772 (8)	C13—C14	1.376 (15)
S2—O5	1.415 (7)	C13—H13	0.9300
S2—O6	1.425 (10)	C14—C15	1.380 (17)
S2—O7	1.455 (9)	C14—H14	0.9300
S2—C25	1.791 (7)	C15—C16	1.411 (16)
O1—H1A	0.8205	C15—H15	0.9300
O1—H1B	0.8202	C16—C17	1.377 (13)
O8—C26	1.343 (11)	C16—C19	1.445 (15)
O8—H8	0.8200	C17—C18	1.457 (12)
O9—C27	1.352 (11)	C18—C21	1.406 (13)
O9—H9	0.8200	C19—C20	1.337 (18)
N1—C1	1.312 (12)	C19—H19	0.9300
N1—C5	1.363 (12)	C20—C21	1.425 (16)
N2—C12	1.330 (12)	C20—H20	0.9300
N2—C6	1.353 (12)	C21—C22	1.394 (16)
N3—C13	1.320 (12)	C22—C23	1.370 (17)
N3—C17	1.343 (11)	C22—H22	0.9300
N4—C24	1.322 (12)	C23—C24	1.390 (15)
N4—C18	1.362 (11)	C23—H23	0.9300
C1—C2	1.387 (16)	C24—H24	0.9300
C1—H1	0.9300	C25—C30	1.377 (11)
C2—C3	1.385 (16)	C25—C26	1.403 (11)
C2—H2	0.9300	C26—C27	1.387 (11)
C3—C4	1.390 (15)	C27—C28	1.389 (12)
C3—H3	0.9300	C28—C29	1.378 (11)
C4—C5	1.402 (14)	C28—H28	0.9300
C4—C7	1.422 (15)	C29—C30	1.388 (11)
C5—C6	1.445 (13)	C30—H30	0.9300
C6—C9	1.402 (13)	O10—H10A	0.8197
C7—C8	1.315 (17)	O10—H10B	0.8197
Cg1···Cg4i	3.734 (7)	Cg3···Cg3iv	3.900 (7)
Cg1···Cg6ii	3.937 (6)	Cg4···Cg4i	3.533 (7)
Cg2···Cg6iii	3.525 (5)	Cg5···Cg5v	3.606 (7)
O1—Cd1—O2	82.9 (3)	C9—C8—H8A	119.3
O1—Cd1—N4	90.6 (3)	C10—C9—C6	118.4 (10)
O2—Cd1—N4	103.4 (3)	C10—C9—C8	122.6 (10)
O1—Cd1—N2	102.6 (3)	C6—C9—C8	118.9 (9)
O2—Cd1—N2	86.8 (3)	C11—C10—C9	119.0 (10)
N4—Cd1—N2	164.4 (3)	C11—C10—H10	120.5
O1—Cd1—N1	95.3 (3)	C9—C10—H10	120.5
O2—Cd1—N1	158.3 (2)	C10—C11—C12	119.0 (10)
N4—Cd1—N1	98.2 (3)	C10—C11—H11	120.5
N2—Cd1—N1	72.5 (3)	C12—C11—H11	120.5
O1—Cd1—N3	161.8 (3)	N2—C12—C11	123.6 (11)
O2—Cd1—N3	95.1 (2)	N2—C12—H12	118.2
N4—Cd1—N3	72.2 (3)	C11—C12—H12	118.2
N2—Cd1—N3	95.4 (3)	N3—C13—C14	124.7 (10)
N1—Cd1—N3	93.1 (3)	N3—C13—H13	117.7
O3—S1—O4	113.4 (4)	C14—C13—H13	117.7
O3—S1—O2	111.6 (4)	C13—C14—C15	118.1 (10)
O4—S1—O2	112.0 (4)	C13—C14—H14	121.0
O3—S1—C29	107.9 (4)	C15—C14—H14	121.0
O4—S1—C29	105.7 (4)	C14—C15—C16	118.8 (10)
O2—S1—C29	105.9 (4)	C14—C15—H15	120.6
O5—S2—O6	113.4 (7)	C16—C15—H15	120.6
O5—S2—O7	112.1 (6)	C17—C16—C15	117.6 (10)
O6—S2—O7	112.6 (8)	C17—C16—C19	120.6 (10)
O5—S2—C25	106.7 (4)	C15—C16—C19	121.6 (11)
O6—S2—C25	106.5 (5)	N3—C17—C16	123.7 (9)
O7—S2—C25	104.9 (5)	N3—C17—C18	117.6 (7)
Cd1—O1—H1A	122.0	C16—C17—C18	118.7 (8)
Cd1—O1—H1B	132.2	N4—C18—C21	121.5 (9)
H1A—O1—H1B	105.1	N4—C18—C17	119.0 (7)
S1—O2—Cd1	132.3 (4)	C21—C18—C17	119.5 (8)
C26—O8—H8	109.5	C20—C19—C16	120.4 (10)
C27—O9—H9	109.5	C20—C19—H19	119.8
C1—N1—C5	119.9 (9)	C16—C19—H19	119.8
C1—N1—Cd1	125.3 (7)	C19—C20—C21	121.5 (11)
C5—N1—Cd1	114.5 (6)	C19—C20—H20	119.3
C12—N2—C6	118.2 (8)	C21—C20—H20	119.3
C12—N2—Cd1	127.0 (7)	C22—C21—C18	117.1 (10)
C6—N2—Cd1	114.8 (6)	C22—C21—C20	123.6 (10)
C13—N3—C17	117.1 (8)	C18—C21—C20	119.3 (11)
C13—N3—Cd1	127.2 (7)	C23—C22—C21	121.5 (10)
C17—N3—Cd1	115.7 (6)	C23—C22—H22	119.3
C24—N4—C18	118.9 (8)	C21—C22—H22	119.3
C24—N4—Cd1	125.6 (7)	C22—C23—C24	117.3 (11)
C18—N4—Cd1	115.4 (6)	C22—C23—H23	121.4
N1—C1—C2	121.3 (11)	C24—C23—H23	121.4
N1—C1—H1	119.4	N4—C24—C23	123.7 (10)
C2—C1—H1	119.4	N4—C24—H24	118.2
C3—C2—C1	120.0 (11)	C23—C24—H24	118.2
C3—C2—H2	120.0	C30—C25—C26	121.5 (7)
C1—C2—H2	120.0	C30—C25—S2	118.6 (6)
C2—C3—C4	119.5 (11)	C26—C25—S2	119.8 (6)
C2—C3—H3	120.3	O8—C26—C27	117.3 (8)
C4—C3—H3	120.3	O8—C26—C25	123.7 (7)
C3—C4—C5	117.2 (10)	C27—C26—C25	119.0 (7)
C3—C4—C7	123.7 (10)	O9—C27—C26	116.5 (8)
C5—C4—C7	119.0 (10)	O9—C27—C28	123.7 (7)
N1—C5—C4	122.0 (9)	C26—C27—C28	119.7 (8)
N1—C5—C6	117.8 (8)	C29—C28—C27	120.1 (7)
C4—C5—C6	120.1 (9)	C29—C28—H28	120.0
N2—C6—C9	121.8 (9)	C27—C28—H28	120.0
N2—C6—C5	119.7 (8)	C28—C29—C30	121.3 (7)
C9—C6—C5	118.5 (9)	C28—C29—S1	120.1 (6)
C8—C7—C4	121.8 (11)	C30—C29—S1	118.6 (6)
C8—C7—H7	119.1	C25—C30—C29	118.3 (8)
C4—C7—H7	119.1	C25—C30—H30	120.9
C7—C8—C9	121.4 (10)	C29—C30—H30	120.9
C7—C8—H8A	119.3	H10A—O10—H10B	104.8
O3—S1—O2—Cd1	−16.4 (7)	N2—C6—C9—C8	176.7 (8)
O4—S1—O2—Cd1	111.8 (5)	C5—C6—C9—C8	−4.7 (12)
C29—S1—O2—Cd1	−133.5 (5)	C7—C8—C9—C10	−179.0 (10)
O1—Cd1—O2—S1	44.5 (6)	C7—C8—C9—C6	2.2 (15)
N4—Cd1—O2—S1	−44.4 (6)	C6—C9—C10—C11	0.7 (14)
N2—Cd1—O2—S1	147.6 (5)	C8—C9—C10—C11	−178.1 (9)
N1—Cd1—O2—S1	130.8 (7)	C9—C10—C11—C12	1.5 (15)
N3—Cd1—O2—S1	−117.3 (5)	C6—N2—C12—C11	1.2 (15)
O1—Cd1—N1—C1	−76.7 (8)	Cd1—N2—C12—C11	−177.0 (8)
O2—Cd1—N1—C1	−160.6 (8)	C10—C11—C12—N2	−2.6 (16)
N4—Cd1—N1—C1	14.7 (8)	C17—N3—C13—C14	−1.5 (15)
N2—Cd1—N1—C1	−178.2 (9)	Cd1—N3—C13—C14	179.5 (8)
N3—Cd1—N1—C1	87.1 (8)	N3—C13—C14—C15	−0.3 (17)
O1—Cd1—N1—C5	108.9 (6)	C13—C14—C15—C16	0.6 (16)
O2—Cd1—N1—C5	25.0 (11)	C14—C15—C16—C17	1.0 (15)
N4—Cd1—N1—C5	−159.7 (6)	C14—C15—C16—C19	176.5 (10)
N2—Cd1—N1—C5	7.4 (6)	C13—N3—C17—C16	3.3 (13)
N3—Cd1—N1—C5	−87.3 (6)	Cd1—N3—C17—C16	−177.7 (7)
O1—Cd1—N2—C12	82.3 (8)	C13—N3—C17—C18	−177.2 (8)
O2—Cd1—N2—C12	0.3 (8)	Cd1—N3—C17—C18	1.9 (9)
N4—Cd1—N2—C12	−131.1 (10)	C15—C16—C17—N3	−3.0 (14)
N1—Cd1—N2—C12	173.9 (8)	C19—C16—C17—N3	−178.6 (8)
N3—Cd1—N2—C12	−94.5 (8)	C15—C16—C17—C18	177.4 (8)
O1—Cd1—N2—C6	−96.0 (6)	C19—C16—C17—C18	1.8 (13)
O2—Cd1—N2—C6	−178.0 (6)	C24—N4—C18—C21	−2.1 (13)
N4—Cd1—N2—C6	50.6 (12)	Cd1—N4—C18—C21	−178.9 (6)
N1—Cd1—N2—C6	−4.4 (6)	C24—N4—C18—C17	175.5 (8)
N3—Cd1—N2—C6	87.2 (6)	Cd1—N4—C18—C17	−1.2 (10)
O1—Cd1—N3—C13	−163.2 (9)	N3—C17—C18—N4	−0.5 (11)
O2—Cd1—N3—C13	−80.4 (8)	C16—C17—C18—N4	179.1 (8)
N4—Cd1—N3—C13	177.1 (8)	N3—C17—C18—C21	177.2 (8)
N2—Cd1—N3—C13	6.8 (8)	C16—C17—C18—C21	−3.2 (12)
N1—Cd1—N3—C13	79.5 (8)	C17—C16—C19—C20	−0.4 (16)
O1—Cd1—N3—C17	17.8 (12)	C15—C16—C19—C20	−175.8 (11)
O2—Cd1—N3—C17	100.6 (6)	C16—C19—C20—C21	0.3 (18)
N4—Cd1—N3—C17	−1.8 (6)	N4—C18—C21—C22	2.5 (13)
N2—Cd1—N3—C17	−172.1 (6)	C17—C18—C21—C22	−175.2 (8)
N1—Cd1—N3—C17	−99.4 (6)	N4—C18—C21—C20	−179.3 (9)
O1—Cd1—N4—C24	11.1 (8)	C17—C18—C21—C20	3.1 (13)
O2—Cd1—N4—C24	93.9 (8)	C19—C20—C21—C22	176.4 (11)
N2—Cd1—N4—C24	−136.4 (10)	C19—C20—C21—C18	−1.7 (17)
N1—Cd1—N4—C24	−84.3 (8)	C18—C21—C22—C23	−2.6 (15)
N3—Cd1—N4—C24	−174.9 (8)	C20—C21—C22—C23	179.3 (11)
O1—Cd1—N4—C18	−172.4 (6)	C21—C22—C23—C24	2.3 (16)
O2—Cd1—N4—C18	−89.6 (6)	C18—N4—C24—C23	1.8 (15)
N2—Cd1—N4—C18	40.1 (12)	Cd1—N4—C24—C23	178.2 (8)
N1—Cd1—N4—C18	92.2 (6)	C22—C23—C24—N4	−1.9 (16)
N3—Cd1—N4—C18	1.6 (6)	O5—S2—C25—C30	35.7 (8)
C5—N1—C1—C2	3.1 (15)	O6—S2—C25—C30	−85.7 (9)
Cd1—N1—C1—C2	−171.0 (8)	O7—S2—C25—C30	154.8 (8)
N1—C1—C2—C3	−2.1 (17)	O5—S2—C25—C26	−146.1 (7)
C1—C2—C3—C4	−0.3 (17)	O6—S2—C25—C26	92.5 (9)
C2—C3—C4—C5	1.5 (15)	O7—S2—C25—C26	−27.0 (9)
C2—C3—C4—C7	−173.9 (10)	C30—C25—C26—O8	−179.2 (8)
C1—N1—C5—C4	−1.8 (13)	S2—C25—C26—O8	2.6 (12)
Cd1—N1—C5—C4	172.9 (7)	C30—C25—C26—C27	−0.7 (12)
C1—N1—C5—C6	175.7 (8)	S2—C25—C26—C27	−178.9 (6)
Cd1—N1—C5—C6	−9.6 (10)	O8—C26—C27—O9	−1.2 (12)
C3—C4—C5—N1	−0.5 (14)	C25—C26—C27—O9	−179.8 (8)
C7—C4—C5—N1	175.2 (9)	O8—C26—C27—C28	−179.9 (8)
C3—C4—C5—C6	−178.0 (9)	C25—C26—C27—C28	1.5 (13)
C7—C4—C5—C6	−2.3 (13)	O9—C27—C28—C29	179.5 (8)
C12—N2—C6—C9	1.2 (13)	C26—C27—C28—C29	−1.9 (13)
Cd1—N2—C6—C9	179.7 (6)	C27—C28—C29—C30	1.5 (12)
C12—N2—C6—C5	−177.3 (8)	C27—C28—C29—S1	−179.5 (6)
Cd1—N2—C6—C5	1.1 (10)	O3—S1—C29—C28	98.1 (7)
N1—C5—C6—N2	5.9 (12)	O4—S1—C29—C28	−23.4 (8)
C4—C5—C6—N2	−176.6 (8)	O2—S1—C29—C28	−142.3 (7)
N1—C5—C6—C9	−172.7 (8)	O3—S1—C29—C30	−82.8 (8)
C4—C5—C6—C9	4.9 (13)	O4—S1—C29—C30	155.6 (7)
C3—C4—C7—C8	175.0 (11)	O2—S1—C29—C30	36.7 (8)
C5—C4—C7—C8	−0.4 (15)	C26—C25—C30—C29	0.3 (12)
C4—C7—C8—C9	0.4 (16)	S2—C25—C30—C29	178.5 (6)
N2—C6—C9—C10	−2.2 (13)	C28—C29—C30—C25	−0.7 (12)
C5—C6—C9—C10	176.4 (8)	S1—C29—C30—C25	−179.7 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O3	0.82	2.15	2.790 (10)	135
O1—H1B···O5vi	0.82	1.93	2.735 (10)	167
O10—H10A···O6vii	0.82	2.22	2.737 (19)	121
O10—H10B···O7	0.82	2.18	2.876 (15)	143
O8—H8···O7	0.82	1.87	2.614 (11)	150
O9—H9···O4viii	0.82	1.90	2.690 (9)	160
C23—H23···O8ix	0.93	2.57	3.465 (15)	163
C23—H23···O9ix	0.93	2.40	3.112 (17)	134

Table 1

Centroid-to-centroid distances (Å)

Cg1, Cg2, Cg3, Cg4, Cg5 and Cg6 are the centroids of N2/C6/C9–C12, N3/C13–C17, N4/C18/C21–C24, C4–C9, C16–C21 and C25–C30, respectively

Cg1⋯Cg4i	3.734 (7)
Cg1⋯Cg6ii	3.937 (6)
Cg2⋯Cg6iii	3.525 (5)
Cg3⋯Cg3iv	3.900 (7)
Cg4⋯Cg4i	3.533 (7)
Cg5⋯Cg5v	3.606 (7)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O3	0.82	2.15	2.790 (10)	135
O1—H1B⋯O5vi	0.82	1.93	2.735 (10)	167
O10—H10A⋯O6vii	0.82	2.22	2.737 (19)	121
O10—H10B⋯O7	0.82	2.18	2.876 (15)	143
O8—H8⋯O7	0.82	1.87	2.614 (11)	150
O9—H9⋯O4viii	0.82	1.90	2.690 (9)	160
C23—H23⋯O8ix	0.93	2.57	3.465 (15)	163
C23—H23⋯O9ix	0.93	2.40	3.112 (17)	134

Symmetry codes: (vi) ; (vii) ; (viii) ; (ix) .