Bis(μ-6-hydroxy-naphthalene-1-carboxyl-ato)bis-[(6-hydroxy-naphthalene-1-car-box-yl-ato)(1,10-phenanthroline)cadmium(II)] tetra-hydrate.

The title complex, [Cd(2)(C(11)H(7)O(3))(4)(C(12)H(8)N(2))(2)]·4H(2)O, has a centrosymmetric binuclear structure in which two Cd(II) atoms are both six-coordinated and bridged by 6-hydroxy-naphthalene-1-carboxyl-ate ligands, with a Cd⋯Cd separation of 3.671 (1) Å. The remaining coordination sites are occupied by two N atoms of a 1,10-phenanthroline ligand and two O atoms of a 6-hydroxy-naphthalene-1-carboxyl-ate ligand. The crystal packing is stabilized by O-H⋯O hydrogen-bonding inter-actions.

Related literature

For the preparation of functional coordination architectures, see: Barnett & Champness (2003 ▶); Comba & Schiek (2003 ▶); Telfer & Kuroda (2003 ▶); Robin & Fromm (2006 ▶); Tranchemontagne et al. (2009 ▶). For complexes with carboxylic acid ligands, see: Bania et al. (2007 ▶); Liu et al. (2006 ▶); Marsh (2004 ▶); Paz & Klinowski (2004 ▶); Qin et al. (2008 ▶); Shi et al. (2005 ▶); Wu et al. (2006 ▶); Xu et al. (2005 ▶); Ye et al. (2005 ▶).

Experimental

Crystal data

[Cd2(C11H7O3)4(C12H8N2)2]·4H2O

M = 1405.96

Monoclinic,

a = 11.7382 (11) Å

b = 15.1433 (14) Å

c = 18.2059 (13) Å

β = 116.430 (4)°

V = 2897.9 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.81 mm−1

T = 296 K

0.28 × 0.21 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.804, T max = 0.868

20423 measured reflections

5096 independent reflections

4064 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.063

S = 1.03

5096 reflections

406 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.41 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809043475/bt5107sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043475/bt5107Isup2.hkl

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

[Cd2(C11H7O3)4(C12H8N2)2]·4H2O	F(000) = 1424
Mr = 1405.96	Dx = 1.611 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.7382 (11) Å	Cell parameters from 5160 reflections
b = 15.1433 (14) Å	θ = 2.4–23.9°
c = 18.2059 (13) Å	µ = 0.81 mm−1
β = 116.430 (4)°	T = 296 K
V = 2897.9 (4) Å3	Block, yellow
Z = 2	0.28 × 0.21 × 0.18 mm

Bruker SMART CCD area-detector diffractometer	5096 independent reflections
Radiation source: fine-focus sealed tube	4064 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.804, Tmax = 0.868	k = −18→18
20423 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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.063	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.022P)2 + 1.6679P] where P = (Fo2 + 2Fc2)/3
5096 reflections	(Δ/σ)max = 0.002
406 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.40 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
Cd1	0.648118 (18)	0.537570 (13)	0.499232 (12)	0.03367 (7)
O1	0.64852 (18)	0.68046 (12)	0.45742 (12)	0.0398 (5)
O2	0.65340 (19)	0.67592 (12)	0.57928 (12)	0.0462 (5)
O3	0.56800 (17)	0.45469 (13)	0.57326 (11)	0.0410 (5)
O4	0.51162 (19)	0.46283 (14)	0.67285 (12)	0.0490 (5)
O5	0.5108 (2)	1.04569 (13)	0.70518 (13)	0.0550 (6)
H5B	0.5048	1.0182	0.7421	0.082*
O6	1.0184 (2)	0.17488 (14)	0.63847 (15)	0.0648 (7)
H6B	1.0940	0.1780	0.6711	0.097*
N1	0.7308 (2)	0.42210 (15)	0.45474 (14)	0.0359 (5)
N2	0.8635 (2)	0.52345 (14)	0.59125 (13)	0.0332 (5)
C1	0.6666 (3)	0.3693 (2)	0.39153 (19)	0.0494 (8)
H1A	0.5793	0.3778	0.3619	0.059*
C2	0.7228 (3)	0.3020 (2)	0.3672 (2)	0.0591 (9)
H2A	0.6736	0.2655	0.3234	0.071*
C3	0.8509 (3)	0.2903 (2)	0.4086 (2)	0.0570 (9)
H3A	0.8906	0.2469	0.3920	0.068*
C4	0.9226 (3)	0.34400 (19)	0.47602 (18)	0.0410 (7)
C5	1.0570 (3)	0.3349 (2)	0.5234 (2)	0.0498 (8)
H5A	1.1002	0.2935	0.5075	0.060*
C6	1.1222 (3)	0.3842 (2)	0.5897 (2)	0.0486 (8)
H6A	1.2097	0.3767	0.6191	0.058*
C7	1.0592 (2)	0.44858 (19)	0.61633 (17)	0.0380 (7)
C8	1.1219 (3)	0.4995 (2)	0.6869 (2)	0.0549 (9)
H8A	1.2089	0.4925	0.7190	0.066*
C9	1.0569 (3)	0.5592 (2)	0.7088 (2)	0.0566 (9)
H9A	1.0981	0.5926	0.7563	0.068*
C10	0.9269 (3)	0.5697 (2)	0.65892 (18)	0.0433 (7)
H10A	0.8828	0.6113	0.6740	0.052*
C11	0.9278 (2)	0.46242 (17)	0.56963 (16)	0.0307 (6)
C12	0.8583 (3)	0.40913 (17)	0.49782 (16)	0.0323 (6)
C13	0.6536 (2)	0.71904 (18)	0.52027 (18)	0.0363 (7)
C14	0.6668 (2)	0.81874 (18)	0.52391 (16)	0.0347 (6)
C15	0.7268 (3)	0.85596 (19)	0.48148 (17)	0.0386 (7)
H15A	0.7517	0.8200	0.4498	0.046*
C16	0.7511 (3)	0.94664 (19)	0.48501 (18)	0.0427 (7)
H16A	0.7918	0.9704	0.4559	0.051*
C17	0.7152 (3)	1.0001 (2)	0.53121 (17)	0.0423 (7)
H17A	0.7340	1.0601	0.5347	0.051*
C18	0.6500 (2)	0.96592 (18)	0.57379 (16)	0.0340 (6)
C19	0.6096 (3)	1.02198 (19)	0.61936 (17)	0.0404 (7)
H19A	0.6262	1.0822	0.6213	0.048*
C20	0.5467 (3)	0.98935 (19)	0.66048 (17)	0.0398 (7)
C21	0.5185 (3)	0.89926 (19)	0.65634 (18)	0.0442 (7)
H21A	0.4743	0.8774	0.6840	0.053*
C22	0.5550 (3)	0.84284 (19)	0.61223 (18)	0.0410 (7)
H22A	0.5339	0.7833	0.6095	0.049*
C23	0.6245 (2)	0.87360 (17)	0.57055 (16)	0.0335 (6)
C24	0.5938 (3)	0.44834 (18)	0.64928 (17)	0.0367 (7)
C25	0.7267 (3)	0.42322 (18)	0.70921 (16)	0.0347 (6)
C26	0.7973 (3)	0.35801 (17)	0.69061 (16)	0.0338 (6)
C27	0.7474 (3)	0.30337 (18)	0.61980 (18)	0.0424 (7)
H27A	0.6619	0.3082	0.5827	0.051*
C28	0.8219 (3)	0.24406 (19)	0.60497 (19)	0.0480 (8)
H28A	0.7865	0.2093	0.5580	0.058*
C29	0.9512 (3)	0.23452 (19)	0.6594 (2)	0.0472 (8)
C30	1.0025 (3)	0.28396 (19)	0.72909 (18)	0.0435 (7)
H30A	1.0880	0.2771	0.7655	0.052*
C31	0.9281 (3)	0.34535 (18)	0.74713 (17)	0.0365 (7)
C32	0.9808 (3)	0.3957 (2)	0.81986 (17)	0.0436 (7)
H32A	1.0659	0.3879	0.8567	0.052*
C33	0.9095 (3)	0.4554 (2)	0.83720 (17)	0.0464 (8)
H33A	0.9455	0.4872	0.8859	0.056*
C34	0.7818 (3)	0.4687 (2)	0.78147 (17)	0.0426 (7)
H34A	0.7335	0.5093	0.7939	0.051*
O1W	0.5418 (2)	0.73556 (15)	0.79947 (13)	0.0609 (6)
H1	0.5421	0.6825	0.8149	0.073*
H2	0.5660	0.7580	0.8469	0.073*
O2W	0.7302 (2)	0.68503 (16)	0.75316 (14)	0.0703 (7)
H3	0.6802	0.7035	0.7721	0.084*
H4	0.7056	0.6987	0.7031	0.084*

	U11	U22	U33	U12	U13	U23
Cd1	0.02669 (11)	0.03283 (12)	0.04132 (13)	0.00375 (9)	0.01496 (9)	0.00190 (10)
O1	0.0447 (12)	0.0340 (11)	0.0414 (12)	0.0026 (9)	0.0198 (10)	−0.0031 (9)
O2	0.0598 (14)	0.0343 (11)	0.0479 (13)	0.0056 (10)	0.0270 (11)	0.0014 (10)
O3	0.0316 (10)	0.0542 (13)	0.0301 (11)	−0.0029 (9)	0.0075 (9)	0.0117 (9)
O4	0.0383 (12)	0.0630 (14)	0.0435 (12)	0.0081 (11)	0.0163 (10)	−0.0038 (11)
O5	0.0792 (16)	0.0432 (13)	0.0489 (13)	0.0118 (12)	0.0342 (12)	−0.0012 (10)
O6	0.0744 (16)	0.0466 (14)	0.0730 (17)	0.0131 (12)	0.0324 (14)	−0.0038 (12)
N1	0.0318 (13)	0.0312 (13)	0.0397 (14)	0.0015 (10)	0.0115 (11)	0.0006 (11)
N2	0.0292 (12)	0.0337 (13)	0.0361 (13)	0.0014 (10)	0.0139 (10)	−0.0006 (10)
C1	0.0446 (18)	0.0463 (19)	0.0471 (19)	−0.0024 (15)	0.0114 (16)	−0.0044 (16)
C2	0.067 (2)	0.046 (2)	0.056 (2)	−0.0020 (18)	0.0203 (19)	−0.0174 (17)
C3	0.069 (2)	0.0444 (19)	0.061 (2)	0.0089 (18)	0.033 (2)	−0.0127 (17)
C4	0.0452 (18)	0.0364 (16)	0.0466 (18)	0.0077 (14)	0.0252 (15)	0.0014 (14)
C5	0.050 (2)	0.0442 (19)	0.066 (2)	0.0179 (16)	0.0366 (18)	0.0073 (17)
C6	0.0339 (17)	0.057 (2)	0.058 (2)	0.0144 (15)	0.0232 (16)	0.0130 (17)
C7	0.0286 (15)	0.0434 (17)	0.0413 (17)	0.0048 (13)	0.0150 (13)	0.0091 (14)
C8	0.0307 (16)	0.073 (2)	0.048 (2)	0.0028 (16)	0.0065 (15)	−0.0003 (18)
C9	0.0446 (19)	0.070 (2)	0.0421 (19)	−0.0030 (17)	0.0071 (16)	−0.0167 (17)
C10	0.0415 (18)	0.0455 (17)	0.0406 (18)	0.0021 (14)	0.0163 (15)	−0.0077 (14)
C11	0.0273 (14)	0.0303 (14)	0.0359 (15)	0.0041 (12)	0.0153 (12)	0.0036 (13)
C12	0.0336 (15)	0.0288 (14)	0.0366 (15)	0.0026 (12)	0.0175 (13)	0.0048 (13)
C13	0.0286 (15)	0.0334 (16)	0.0427 (18)	0.0056 (12)	0.0121 (14)	0.0006 (14)
C14	0.0280 (14)	0.0348 (15)	0.0349 (16)	0.0049 (12)	0.0083 (13)	0.0021 (12)
C15	0.0352 (16)	0.0419 (17)	0.0360 (16)	0.0018 (13)	0.0134 (13)	0.0005 (13)
C16	0.0426 (17)	0.0462 (19)	0.0410 (17)	−0.0068 (14)	0.0202 (15)	0.0031 (14)
C17	0.0462 (18)	0.0326 (15)	0.0426 (18)	−0.0050 (14)	0.0148 (15)	0.0028 (14)
C18	0.0309 (14)	0.0323 (15)	0.0297 (14)	0.0017 (13)	0.0053 (12)	0.0023 (13)
C19	0.0437 (17)	0.0351 (17)	0.0333 (16)	0.0014 (14)	0.0091 (14)	0.0011 (13)
C20	0.0432 (17)	0.0392 (17)	0.0327 (16)	0.0085 (14)	0.0130 (14)	0.0006 (13)
C21	0.0475 (18)	0.0427 (18)	0.0476 (18)	0.0024 (15)	0.0259 (15)	0.0053 (15)
C22	0.0408 (17)	0.0339 (16)	0.0490 (18)	0.0008 (13)	0.0206 (15)	0.0017 (14)
C23	0.0309 (15)	0.0321 (15)	0.0309 (15)	0.0026 (12)	0.0078 (12)	0.0038 (12)
C24	0.0340 (16)	0.0339 (16)	0.0351 (16)	−0.0029 (13)	0.0091 (13)	0.0011 (13)
C25	0.0339 (15)	0.0378 (15)	0.0297 (15)	0.0010 (13)	0.0118 (13)	0.0065 (13)
C26	0.0359 (15)	0.0317 (15)	0.0300 (15)	−0.0030 (12)	0.0111 (13)	0.0048 (12)
C27	0.0440 (17)	0.0339 (16)	0.0391 (17)	−0.0035 (14)	0.0095 (14)	0.0031 (14)
C28	0.062 (2)	0.0311 (16)	0.0436 (18)	−0.0045 (15)	0.0170 (17)	−0.0027 (14)
C29	0.062 (2)	0.0304 (16)	0.055 (2)	0.0074 (15)	0.0315 (18)	0.0066 (15)
C30	0.0400 (17)	0.0386 (17)	0.0448 (19)	0.0066 (14)	0.0124 (15)	0.0089 (15)
C31	0.0370 (16)	0.0338 (16)	0.0342 (16)	0.0014 (13)	0.0119 (13)	0.0077 (13)
C32	0.0370 (16)	0.0505 (19)	0.0340 (16)	0.0031 (15)	0.0076 (14)	0.0050 (14)
C33	0.0462 (18)	0.055 (2)	0.0288 (15)	−0.0015 (16)	0.0087 (14)	−0.0054 (15)
C34	0.0422 (17)	0.0482 (18)	0.0359 (16)	0.0041 (15)	0.0161 (14)	0.0001 (15)
O1W	0.0763 (16)	0.0583 (15)	0.0430 (13)	−0.0083 (13)	0.0220 (12)	−0.0003 (11)
O2W	0.0676 (16)	0.0829 (18)	0.0647 (16)	0.0084 (14)	0.0332 (13)	0.0077 (14)

Cd1—O3i	2.2827 (18)	C11—C12	1.441 (4)
Cd1—O1	2.2945 (18)	C13—C14	1.516 (4)
Cd1—N1	2.314 (2)	C14—C15	1.377 (4)
Cd1—O3	2.3247 (18)	C14—C23	1.426 (4)
Cd1—N2	2.339 (2)	C15—C16	1.398 (4)
Cd1—O2	2.5370 (19)	C15—H15A	0.9300
Cd1—C13	2.771 (3)	C16—C17	1.363 (4)
Cd1—O4i	2.846 (2)	C16—H16A	0.9300
Cd1—Cd1i	3.6706 (5)	C17—C18	1.408 (4)
O1—C13	1.262 (3)	C17—H17A	0.9300
O2—C13	1.258 (3)	C18—C19	1.409 (4)
O3—C24	1.282 (3)	C18—C23	1.425 (4)
O3—Cd1i	2.2827 (18)	C19—C20	1.357 (4)
O4—C24	1.238 (3)	C19—H19A	0.9300
O4—Cd1i	2.846 (2)	C20—C21	1.398 (4)
O5—C20	1.369 (3)	C21—C22	1.366 (4)
O5—H5B	0.8200	C21—H21A	0.9300
O6—C29	1.360 (3)	C22—C23	1.418 (4)
O6—H6B	0.8200	C22—H22A	0.9300
N1—C1	1.326 (4)	C24—C25	1.501 (4)
N1—C12	1.360 (3)	C25—C34	1.366 (4)
N2—C10	1.322 (3)	C25—C26	1.424 (4)
N2—C11	1.358 (3)	C26—C27	1.420 (4)
C1—C2	1.389 (4)	C26—C31	1.431 (4)
C1—H1A	0.9300	C27—C28	1.362 (4)
C2—C3	1.361 (4)	C27—H27A	0.9300
C2—H2A	0.9300	C28—C29	1.403 (4)
C3—C4	1.399 (4)	C28—H28A	0.9300
C3—H3A	0.9300	C29—C30	1.362 (4)
C4—C12	1.402 (4)	C30—C31	1.411 (4)
C4—C5	1.428 (4)	C30—H30A	0.9300
C5—C6	1.334 (4)	C31—C32	1.410 (4)
C5—H5A	0.9300	C32—C33	1.360 (4)
C6—C7	1.432 (4)	C32—H32A	0.9300
C6—H6A	0.9300	C33—C34	1.402 (4)
C7—C8	1.394 (4)	C33—H33A	0.9300
C7—C11	1.406 (4)	C34—H34A	0.9300
C8—C9	1.353 (4)	O1W—H1	0.8500
C8—H8A	0.9300	O1W—H2	0.8500
C9—C10	1.395 (4)	O2W—H3	0.8499
C9—H9A	0.9300	O2W—H4	0.8502
C10—H10A	0.9300
O3i—Cd1—O1	85.73 (7)	C9—C10—H10A	118.5
O3i—Cd1—N1	111.57 (8)	N2—C11—C7	121.9 (2)
O1—Cd1—N1	122.24 (7)	N2—C11—C12	118.7 (2)
O3i—Cd1—O3	74.38 (7)	C7—C11—C12	119.4 (2)
O1—Cd1—O3	139.69 (7)	N1—C12—C4	122.1 (3)
N1—Cd1—O3	97.80 (8)	N1—C12—C11	118.4 (2)
O3i—Cd1—N2	170.86 (7)	C4—C12—C11	119.5 (2)
O1—Cd1—N2	99.36 (7)	O2—C13—O1	121.1 (3)
N1—Cd1—N2	72.17 (8)	O2—C13—C14	121.2 (3)
O3—Cd1—N2	97.04 (7)	O1—C13—C14	117.6 (3)
O3i—Cd1—O2	91.52 (7)	O2—C13—Cd1	66.08 (15)
O1—Cd1—O2	53.75 (7)	O1—C13—Cd1	55.04 (14)
N1—Cd1—O2	156.67 (7)	C14—C13—Cd1	171.5 (2)
O3—Cd1—O2	91.47 (7)	C15—C14—C23	119.8 (3)
N2—Cd1—O2	85.51 (7)	C15—C14—C13	116.8 (3)
O3i—Cd1—C13	88.87 (7)	C23—C14—C13	123.4 (3)
O1—Cd1—C13	26.80 (7)	C14—C15—C16	121.4 (3)
N1—Cd1—C13	144.11 (8)	C14—C15—H15A	119.3
O3—Cd1—C13	116.46 (8)	C16—C15—H15A	119.3
N2—Cd1—C13	92.32 (8)	C17—C16—C15	119.9 (3)
O2—Cd1—C13	26.95 (7)	C17—C16—H16A	120.0
O3i—Cd1—O4i	49.13 (6)	C15—C16—H16A	120.0
O1—Cd1—O4i	74.60 (6)	C16—C17—C18	121.0 (3)
N1—Cd1—O4i	77.68 (7)	C16—C17—H17A	119.5
O3—Cd1—O4i	113.50 (6)	C18—C17—H17A	119.5
N2—Cd1—O4i	139.51 (7)	C17—C18—C19	120.7 (3)
O2—Cd1—O4i	118.02 (6)	C17—C18—C23	119.6 (3)
C13—Cd1—O4i	96.75 (7)	C19—C18—C23	119.7 (3)
O3i—Cd1—Cd1i	37.58 (5)	C20—C19—C18	120.9 (3)
O1—Cd1—Cd1i	115.89 (5)	C20—C19—H19A	119.5
N1—Cd1—Cd1i	108.34 (6)	C18—C19—H19A	119.5
O3—Cd1—Cd1i	36.79 (4)	C19—C20—O5	119.2 (3)
N2—Cd1—Cd1i	133.75 (5)	C19—C20—C21	120.0 (3)
O2—Cd1—Cd1i	91.87 (5)	O5—C20—C21	120.8 (3)
C13—Cd1—Cd1i	105.66 (6)	C22—C21—C20	120.9 (3)
O4i—Cd1—Cd1i	81.11 (4)	C22—C21—H21A	119.5
C13—O1—Cd1	98.15 (17)	C20—C21—H21A	119.5
C13—O2—Cd1	86.96 (16)	C21—C22—C23	121.0 (3)
C24—O3—Cd1i	107.21 (16)	C21—C22—H22A	119.5
C24—O3—Cd1	134.76 (17)	C23—C22—H22A	119.5
Cd1i—O3—Cd1	105.62 (7)	C22—C23—C18	117.4 (3)
C24—O4—Cd1i	81.45 (16)	C22—C23—C14	124.3 (3)
C20—O5—H5B	109.5	C18—C23—C14	118.3 (3)
C29—O6—H6B	109.5	O4—C24—O3	121.0 (3)
C1—N1—C12	117.9 (2)	O4—C24—C25	120.7 (3)
C1—N1—Cd1	126.5 (2)	O3—C24—C25	118.3 (2)
C12—N1—Cd1	115.64 (17)	C34—C25—C26	120.2 (3)
C10—N2—C11	118.4 (2)	C34—C25—C24	117.8 (3)
C10—N2—Cd1	126.87 (19)	C26—C25—C24	122.0 (2)
C11—N2—Cd1	114.69 (16)	C27—C26—C25	124.9 (3)
N1—C1—C2	123.5 (3)	C27—C26—C31	116.8 (3)
N1—C1—H1A	118.3	C25—C26—C31	118.3 (2)
C2—C1—H1A	118.3	C28—C27—C26	121.5 (3)
C3—C2—C1	119.0 (3)	C28—C27—H27A	119.2
C3—C2—H2A	120.5	C26—C27—H27A	119.2
C1—C2—H2A	120.5	C27—C28—C29	121.1 (3)
C2—C3—C4	119.6 (3)	C27—C28—H28A	119.4
C2—C3—H3A	120.2	C29—C28—H28A	119.4
C4—C3—H3A	120.2	O6—C29—C30	123.7 (3)
C3—C4—C12	117.9 (3)	O6—C29—C28	116.8 (3)
C3—C4—C5	123.0 (3)	C30—C29—C28	119.5 (3)
C12—C4—C5	119.1 (3)	C29—C30—C31	121.1 (3)
C6—C5—C4	121.9 (3)	C29—C30—H30A	119.4
C6—C5—H5A	119.1	C31—C30—H30A	119.4
C4—C5—H5A	119.1	C32—C31—C30	121.1 (3)
C5—C6—C7	120.8 (3)	C32—C31—C26	119.0 (3)
C5—C6—H6A	119.6	C30—C31—C26	119.9 (3)
C7—C6—H6A	119.6	C33—C32—C31	121.3 (3)
C8—C7—C11	117.5 (3)	C33—C32—H32A	119.4
C8—C7—C6	123.2 (3)	C31—C32—H32A	119.4
C11—C7—C6	119.3 (3)	C32—C33—C34	119.9 (3)
C9—C8—C7	120.4 (3)	C32—C33—H33A	120.1
C9—C8—H8A	119.8	C34—C33—H33A	120.1
C7—C8—H8A	119.8	C25—C34—C33	121.3 (3)
C8—C9—C10	118.8 (3)	C25—C34—H34A	119.3
C8—C9—H9A	120.6	C33—C34—H34A	119.3
C10—C9—H9A	120.6	H1—O1W—H2	95.3
N2—C10—C9	123.1 (3)	H3—O2W—H4	112.8
N2—C10—H10A	118.5
O3i—Cd1—O1—C13	95.96 (16)	C3—C4—C12—N1	−1.3 (4)
N1—Cd1—O1—C13	−151.16 (15)	C5—C4—C12—N1	179.1 (3)
O3—Cd1—O1—C13	36.3 (2)	C3—C4—C12—C11	176.6 (3)
N2—Cd1—O1—C13	−76.40 (17)	C5—C4—C12—C11	−3.0 (4)
O2—Cd1—O1—C13	0.94 (15)	N2—C11—C12—N1	−0.2 (4)
O4i—Cd1—O1—C13	144.66 (17)	C7—C11—C12—N1	178.4 (2)
Cd1i—Cd1—O1—C13	72.82 (16)	N2—C11—C12—C4	−178.1 (2)
O3i—Cd1—O2—C13	−84.52 (16)	C7—C11—C12—C4	0.4 (4)
O1—Cd1—O2—C13	−0.94 (15)	Cd1—O2—C13—O1	1.6 (3)
N1—Cd1—O2—C13	87.3 (2)	Cd1—O2—C13—C14	−175.2 (2)
O3—Cd1—O2—C13	−158.93 (16)	Cd1—O1—C13—O2	−1.8 (3)
N2—Cd1—O2—C13	104.13 (16)	Cd1—O1—C13—C14	175.09 (19)
O4i—Cd1—O2—C13	−41.20 (17)	O3i—Cd1—C13—O2	95.57 (16)
Cd1i—Cd1—O2—C13	−122.12 (15)	O1—Cd1—C13—O2	178.3 (3)
O3i—Cd1—O3—C24	−135.2 (3)	N1—Cd1—C13—O2	−137.55 (16)
O1—Cd1—O3—C24	−71.9 (3)	O3—Cd1—C13—O2	23.67 (17)
N1—Cd1—O3—C24	114.5 (3)	N2—Cd1—C13—O2	−75.37 (16)
N2—Cd1—O3—C24	41.6 (3)	O4i—Cd1—C13—O2	144.16 (15)
O2—Cd1—O3—C24	−44.1 (3)	Cd1i—Cd1—C13—O2	61.53 (16)
C13—Cd1—O3—C24	−54.6 (3)	O3i—Cd1—C13—O1	−82.76 (16)
O4i—Cd1—O3—C24	−165.6 (2)	N1—Cd1—C13—O1	44.1 (2)
Cd1i—Cd1—O3—C24	−135.2 (3)	O3—Cd1—C13—O1	−154.66 (15)
O3i—Cd1—O3—Cd1i	0.0	N2—Cd1—C13—O1	106.30 (16)
O1—Cd1—O3—Cd1i	63.32 (13)	O2—Cd1—C13—O1	−178.3 (3)
N1—Cd1—O3—Cd1i	−110.30 (9)	O4i—Cd1—C13—O1	−34.17 (16)
N2—Cd1—O3—Cd1i	176.82 (8)	Cd1i—Cd1—C13—O1	−116.79 (15)
O2—Cd1—O3—Cd1i	91.16 (8)	O2—C13—C14—C15	148.9 (3)
C13—Cd1—O3—Cd1i	80.68 (9)	O1—C13—C14—C15	−28.0 (4)
O4i—Cd1—O3—Cd1i	−30.40 (10)	O2—C13—C14—C23	−28.9 (4)
O3i—Cd1—N1—C1	4.9 (3)	O1—C13—C14—C23	154.2 (3)
O1—Cd1—N1—C1	−94.0 (2)	C23—C14—C15—C16	2.0 (4)
O3—Cd1—N1—C1	81.1 (2)	C13—C14—C15—C16	−175.9 (3)
N2—Cd1—N1—C1	176.0 (3)	C14—C15—C16—C17	0.0 (4)
O2—Cd1—N1—C1	−166.4 (2)	C15—C16—C17—C18	−2.0 (4)
C13—Cd1—N1—C1	−115.8 (2)	C16—C17—C18—C19	−178.0 (3)
O4i—Cd1—N1—C1	−31.4 (2)	C16—C17—C18—C23	1.9 (4)
Cd1i—Cd1—N1—C1	44.8 (2)	C17—C18—C19—C20	180.0 (3)
O3i—Cd1—N1—C12	−176.18 (17)	C23—C18—C19—C20	0.1 (4)
O1—Cd1—N1—C12	84.91 (19)	C18—C19—C20—O5	178.9 (2)
O3—Cd1—N1—C12	−99.96 (18)	C18—C19—C20—C21	−1.6 (4)
N2—Cd1—N1—C12	−5.04 (18)	C19—C20—C21—C22	0.9 (4)
O2—Cd1—N1—C12	12.6 (3)	O5—C20—C21—C22	−179.6 (3)
C13—Cd1—N1—C12	63.1 (2)	C20—C21—C22—C23	1.2 (4)
O4i—Cd1—N1—C12	147.59 (19)	C21—C22—C23—C18	−2.5 (4)
Cd1i—Cd1—N1—C12	−136.24 (17)	C21—C22—C23—C14	179.5 (3)
O1—Cd1—N2—C10	61.9 (2)	C17—C18—C23—C22	−178.0 (3)
N1—Cd1—N2—C10	−177.1 (2)	C19—C18—C23—C22	1.9 (4)
O2—Cd1—N2—C10	9.8 (2)	C17—C18—C23—C14	0.2 (4)
C13—Cd1—N2—C10	35.9 (2)	C19—C18—C23—C14	−180.0 (2)
O4i—Cd1—N2—C10	139.1 (2)	C15—C14—C23—C22	176.0 (3)
Cd1i—Cd1—N2—C10	−78.5 (2)	C13—C14—C23—C22	−6.3 (4)
O1—Cd1—N2—C11	−116.08 (18)	C15—C14—C23—C18	−2.1 (4)
N1—Cd1—N2—C11	4.91 (17)	C13—C14—C23—C18	175.7 (2)
O2—Cd1—N2—C11	−168.20 (18)	Cd1i—O4—C24—O3	9.9 (2)
C13—Cd1—N2—C11	−142.10 (18)	Cd1i—O4—C24—C25	−170.3 (3)
O4i—Cd1—N2—C11	−38.9 (2)	Cd1i—O3—C24—O4	−12.9 (3)
Cd1i—Cd1—N2—C11	103.51 (17)	Cd1—O3—C24—O4	121.9 (3)
C12—N1—C1—C2	−0.1 (4)	Cd1i—O3—C24—C25	167.38 (19)
Cd1—N1—C1—C2	178.8 (2)	Cd1—O3—C24—C25	−57.8 (4)
N1—C1—C2—C3	−1.8 (5)	O4—C24—C25—C34	−43.3 (4)
C1—C2—C3—C4	2.1 (5)	O3—C24—C25—C34	136.4 (3)
C2—C3—C4—C12	−0.7 (5)	O4—C24—C25—C26	140.3 (3)
C2—C3—C4—C5	178.9 (3)	O3—C24—C25—C26	−40.0 (4)
C3—C4—C5—C6	−176.8 (3)	C34—C25—C26—C27	176.1 (3)
C12—C4—C5—C6	2.8 (5)	C24—C25—C26—C27	−7.6 (4)
C4—C5—C6—C7	0.2 (5)	C34—C25—C26—C31	−3.4 (4)
C5—C6—C7—C8	177.5 (3)	C24—C25—C26—C31	172.8 (2)
C5—C6—C7—C11	−2.8 (4)	C25—C26—C27—C28	178.1 (3)
C11—C7—C8—C9	0.5 (5)	C31—C26—C27—C28	−2.4 (4)
C6—C7—C8—C9	−179.9 (3)	C26—C27—C28—C29	0.1 (4)
C7—C8—C9—C10	−1.1 (5)	C27—C28—C29—O6	−178.7 (3)
C11—N2—C10—C9	0.4 (4)	C27—C28—C29—C30	1.5 (5)
Cd1—N2—C10—C9	−177.5 (2)	O6—C29—C30—C31	179.5 (3)
C8—C9—C10—N2	0.7 (5)	C28—C29—C30—C31	−0.7 (4)
C10—N2—C11—C7	−1.0 (4)	C29—C30—C31—C32	179.1 (3)
Cd1—N2—C11—C7	177.1 (2)	C29—C30—C31—C26	−1.6 (4)
C10—N2—C11—C12	177.4 (2)	C27—C26—C31—C32	−177.7 (2)
Cd1—N2—C11—C12	−4.4 (3)	C25—C26—C31—C32	1.9 (4)
C8—C7—C11—N2	0.6 (4)	C27—C26—C31—C30	3.1 (4)
C6—C7—C11—N2	−179.0 (3)	C25—C26—C31—C30	−177.3 (2)
C8—C7—C11—C12	−177.9 (3)	C30—C31—C32—C33	179.6 (3)
C6—C7—C11—C12	2.5 (4)	C26—C31—C32—C33	0.3 (4)
C1—N1—C12—C4	1.7 (4)	C31—C32—C33—C34	−1.1 (5)
Cd1—N1—C12—C4	−177.4 (2)	C26—C25—C34—C33	2.7 (4)
C1—N1—C12—C11	−176.2 (2)	C24—C25—C34—C33	−173.7 (3)
Cd1—N1—C12—C11	4.7 (3)	C32—C33—C34—C25	−0.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1···O5ii	0.85	2.15	2.934 (3)	154
O1W—H2···O1iii	0.85	2.03	2.872 (3)	170
O2W—H3···O1W	0.85	1.96	2.801 (4)	170
O2W—H4···O2	0.85	2.08	2.883 (3)	156
O5—H5B···O4iv	0.82	1.84	2.664 (3)	176
O6—H6B···O2Wv	0.82	1.91	2.728 (4)	180

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1⋯O5i	0.85	2.15	2.934 (3)	154
O1W—H2⋯O1ii	0.85	2.03	2.872 (3)	170
O2W—H3⋯O1W	0.85	1.96	2.801 (4)	170
O2W—H4⋯O2	0.85	2.08	2.883 (3)	156
O5—H5B⋯O4iii	0.82	1.84	2.664 (3)	176
O6—H6B⋯O2Wiv	0.82	1.91	2.728 (4)	180

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