Propane-1,2-diaminium bis-(pyridine-2,6-dicarboxyl-ato-κO,N,O)cadmate dihydrate.

The reaction of cadmium nitrate dihydrate, propane-1,2-diamine and pyridine-2,6-dicarb-oxy-lic acid in a 1:1:2 molar ratio in an aqueous solution resulted in the formation of the title compound, (C(3)H(12)N(2))[Cd(C(7)H(3)NO(4))(2)]·2H(2)O or (p-1,2-daH(2))-[Cd(pydc)(2)]·2H(2)O (where p-1,2-da is propane-1,2-diamine and pydcH(2) is pyridine-2,6-dicarb-oxy-lic acid). The Cd(II) ion is coordinated by four O and two N atoms of two pydc ligands in a distorted octa-hedral environment. The structure also contains two uncoordinated water mol-ecules. In the crystal, there are several inter-molecular N-H⋯O, O-H⋯O and weak C-H⋯O hydrogen bonds. There are also π-π stacking inter-actions between the pyridine rings of pydc units, with centroid-centroid distances of 3.4708 (16) Å.

Related literature

For related proton-transfer compounds reported by our group, see: Aghabozorg et al. (2008a ▶,b ▶,c ▶,d ▶); Pasdar et al. (2011 ▶).

Experimental

Crystal data

(C3H12N2)[Cd(C7H3NO4)2]·2H2O

M = 554.80

Triclinic,

a = 8.6227 (17) Å

b = 10.133 (2) Å

c = 13.448 (3) Å

α = 81.36 (3)°

β = 76.73 (3)°

γ = 65.38 (3)°

V = 1037.7 (5) Å3

Z = 2

Mo Kα radiation

μ = 1.12 mm−1

T = 298 K

0.30 × 0.20 × 0.15 mm

Data collection

Stoe IPDS 2T diffractometer

Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005 ▶)T min = 0.764, T max = 0.842

11690 measured reflections

5554 independent reflections

4562 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.063

S = 1.02

5554 reflections

330 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 e Å−3

Δρmin = −0.37 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; 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/S160053681102438X/bt5545sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681102438X/bt5545Isup2.hkl

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

(C3H12N2)[Cd(C7H3NO4)2]·2H2O	Z = 2
Mr = 554.80	F(000) = 560
Triclinic, P1	Dx = 1.776 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6227 (17) Å	Cell parameters from 5554 reflections
b = 10.133 (2) Å	θ = 2.2–29.2°
c = 13.448 (3) Å	µ = 1.12 mm−1
α = 81.36 (3)°	T = 298 K
β = 76.73 (3)°	Plate, colorless
γ = 65.38 (3)°	0.3 × 0.2 × 0.15 mm
V = 1037.7 (5) Å3

Stoe IPDS 2T diffractometer	5554 independent reflections
Radiation source: fine-focus sealed tube	4562 reflections with I > 2σ(I)
graphite	Rint = 0.035
Detector resolution: 0.15 mm pixels mm-1	θmax = 29.2°, θmin = 2.2°
rotation method scans	h = −10→11
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005)	k = −13→13
Tmin = 0.764, Tmax = 0.842	l = −18→18
11690 measured reflections

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.063	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.030P)2 + 0.1592P] where P = (Fo2 + 2Fc2)/3
5554 reflections	(Δ/σ)max = 0.002
330 parameters	Δρmax = 0.50 e Å−3
1 restraint	Δρmin = −0.37 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
N3	1.0640 (3)	1.0203 (2)	0.73941 (18)	0.0427 (4)
Cd1	0.66437 (2)	0.504594 (16)	0.721726 (12)	0.03837 (6)
O2	0.2288 (2)	0.84128 (17)	0.89531 (14)	0.0470 (4)
O1	0.3826 (2)	0.68084 (17)	0.77635 (13)	0.0459 (4)
C2	0.5023 (3)	0.66583 (19)	0.92189 (15)	0.0292 (4)
N1	0.6429 (2)	0.55580 (16)	0.88029 (12)	0.0291 (3)
C6	0.7749 (3)	0.4828 (2)	0.92965 (15)	0.0296 (4)
O5	0.7653 (2)	0.69575 (17)	0.65361 (13)	0.0472 (4)
C1	0.3595 (3)	0.7347 (2)	0.85908 (16)	0.0345 (4)
O3	0.8962 (2)	0.31965 (15)	0.79612 (12)	0.0404 (3)
O7	0.6154 (2)	0.31945 (16)	0.67431 (12)	0.0443 (4)
N2	0.7307 (2)	0.50583 (17)	0.55184 (12)	0.0318 (3)
O4	1.0562 (2)	0.29857 (19)	0.91131 (16)	0.0581 (5)
O6	0.8533 (3)	0.80395 (19)	0.50805 (16)	0.0598 (5)
C5	0.7702 (3)	0.5199 (2)	1.02547 (16)	0.0363 (4)
H5	0.8626	0.4691	1.0595	0.044*
C9	0.7864 (3)	0.6038 (2)	0.49661 (16)	0.0352 (4)
C4	0.6252 (3)	0.6340 (2)	1.06974 (16)	0.0385 (5)
H4	0.6193	0.6606	1.1342	0.046*
C3	0.4892 (3)	0.7083 (2)	1.01798 (16)	0.0355 (4)
H3	0.3909	0.7851	1.0469	0.043*
C7	0.9229 (3)	0.3556 (2)	0.87480 (16)	0.0340 (4)
C14	0.6464 (3)	0.3028 (2)	0.58002 (17)	0.0382 (5)
C13	0.7083 (3)	0.4078 (2)	0.50696 (16)	0.0330 (4)
C8	0.8043 (3)	0.7107 (2)	0.55696 (19)	0.0408 (5)
O8	0.6343 (3)	0.20351 (18)	0.54186 (14)	0.0550 (5)
N4	0.6575 (3)	0.9894 (2)	0.71014 (17)	0.0395 (4)
C16	0.7838 (3)	0.9958 (2)	0.76668 (16)	0.0362 (4)
H16	0.7338	1.0911	0.7957	0.043*
C12	0.7429 (3)	0.4046 (3)	0.40160 (17)	0.0416 (5)
H12	0.7277	0.3358	0.3706	0.050*
C15	0.9497 (3)	0.9831 (2)	0.69164 (18)	0.0410 (5)
H15A	1.0104	0.8845	0.6697	0.049*
H15B	0.9212	1.0482	0.6317	0.049*
C11	0.8002 (3)	0.5050 (3)	0.34338 (18)	0.0505 (6)
H11	0.8236	0.5048	0.2724	0.061*
C10	0.8232 (3)	0.6062 (3)	0.39052 (18)	0.0450 (5)
H10	0.8623	0.6743	0.3520	0.054*
C17	0.8098 (4)	0.8803 (3)	0.8543 (2)	0.0649 (8)
H17A	0.7007	0.8971	0.8997	0.097*
H17B	0.8906	0.8847	0.8910	0.097*
H17C	0.8545	0.7861	0.8277	0.097*
O9	0.3551 (3)	0.0640 (3)	0.8606 (2)	0.0659 (6)
O10	0.3774 (3)	0.9659 (3)	0.60376 (17)	0.0623 (5)
H4C	0.553 (4)	1.013 (3)	0.754 (2)	0.050 (8)*
H4B	0.696 (4)	0.906 (3)	0.690 (2)	0.057 (8)*
H4A	0.651 (4)	1.054 (3)	0.655 (2)	0.059 (8)*
H9A	0.276 (6)	0.135 (5)	0.869 (3)	0.090 (13)*
H10B	0.404 (5)	0.899 (4)	0.577 (3)	0.076 (13)*
H10A	0.341 (8)	1.039 (7)	0.558 (5)	0.16 (2)*
H9B	0.317 (5)	−0.001 (4)	0.883 (3)	0.081 (12)*
H3C	1.100 (4)	0.957 (3)	0.7943 (18)	0.061 (9)*
H3A	1.159 (4)	1.011 (3)	0.693 (2)	0.057 (8)*
H3B	1.013 (4)	1.108 (4)	0.758 (2)	0.061 (9)*

	U11	U22	U33	U12	U13	U23
N3	0.0314 (10)	0.0350 (10)	0.0587 (13)	−0.0071 (8)	−0.0084 (10)	−0.0124 (9)
Cd1	0.05293 (11)	0.03011 (8)	0.02906 (8)	−0.01047 (6)	−0.01066 (6)	−0.00649 (5)
O2	0.0355 (9)	0.0356 (8)	0.0624 (11)	−0.0006 (7)	−0.0148 (8)	−0.0127 (7)
O1	0.0479 (9)	0.0413 (8)	0.0447 (9)	−0.0050 (7)	−0.0223 (7)	−0.0084 (7)
C2	0.0304 (10)	0.0243 (8)	0.0341 (9)	−0.0113 (7)	−0.0054 (8)	−0.0048 (7)
N1	0.0313 (9)	0.0251 (7)	0.0312 (8)	−0.0094 (6)	−0.0077 (7)	−0.0048 (6)
C6	0.0282 (10)	0.0279 (8)	0.0342 (9)	−0.0127 (7)	−0.0053 (8)	−0.0022 (7)
O5	0.0632 (11)	0.0349 (8)	0.0474 (9)	−0.0195 (7)	−0.0135 (8)	−0.0092 (7)
C1	0.0345 (11)	0.0270 (9)	0.0423 (11)	−0.0099 (8)	−0.0119 (9)	−0.0027 (8)
O3	0.0421 (9)	0.0311 (7)	0.0386 (8)	−0.0030 (6)	−0.0073 (7)	−0.0093 (6)
O7	0.0632 (11)	0.0335 (7)	0.0388 (8)	−0.0203 (7)	−0.0113 (8)	−0.0035 (6)
N2	0.0331 (9)	0.0270 (7)	0.0313 (8)	−0.0056 (7)	−0.0093 (7)	−0.0040 (6)
O4	0.0351 (9)	0.0504 (10)	0.0833 (14)	0.0012 (8)	−0.0240 (9)	−0.0222 (9)
O6	0.0699 (13)	0.0428 (9)	0.0738 (13)	−0.0306 (9)	−0.0176 (11)	0.0068 (9)
C5	0.0360 (11)	0.0402 (10)	0.0379 (11)	−0.0172 (9)	−0.0134 (9)	−0.0018 (8)
C9	0.0294 (10)	0.0316 (9)	0.0384 (10)	−0.0051 (8)	−0.0084 (8)	−0.0022 (8)
C4	0.0453 (13)	0.0426 (11)	0.0329 (10)	−0.0197 (10)	−0.0074 (9)	−0.0111 (8)
C3	0.0352 (11)	0.0335 (9)	0.0371 (10)	−0.0121 (8)	−0.0028 (9)	−0.0108 (8)
C7	0.0301 (10)	0.0257 (9)	0.0429 (11)	−0.0085 (8)	−0.0045 (9)	−0.0036 (8)
C14	0.0404 (12)	0.0270 (9)	0.0453 (12)	−0.0053 (8)	−0.0168 (10)	−0.0070 (8)
C13	0.0308 (10)	0.0286 (9)	0.0352 (10)	−0.0026 (8)	−0.0111 (8)	−0.0089 (7)
C8	0.0362 (12)	0.0285 (9)	0.0538 (13)	−0.0067 (8)	−0.0123 (10)	−0.0037 (9)
O8	0.0795 (13)	0.0384 (8)	0.0578 (10)	−0.0255 (9)	−0.0245 (10)	−0.0093 (7)
N4	0.0381 (11)	0.0341 (10)	0.0483 (11)	−0.0121 (8)	−0.0127 (9)	−0.0080 (8)
C16	0.0352 (11)	0.0325 (10)	0.0414 (11)	−0.0106 (8)	−0.0103 (9)	−0.0072 (8)
C12	0.0379 (12)	0.0452 (12)	0.0369 (11)	−0.0055 (9)	−0.0115 (9)	−0.0147 (9)
C15	0.0353 (12)	0.0378 (11)	0.0477 (12)	−0.0093 (9)	−0.0085 (10)	−0.0110 (9)
C11	0.0472 (14)	0.0666 (16)	0.0287 (10)	−0.0145 (12)	−0.0042 (10)	−0.0058 (10)
C10	0.0390 (12)	0.0520 (13)	0.0385 (11)	−0.0160 (10)	−0.0037 (10)	0.0018 (10)
C17	0.0664 (19)	0.0728 (19)	0.0647 (18)	−0.0363 (16)	−0.0286 (15)	0.0201 (15)
O9	0.0449 (11)	0.0434 (10)	0.0973 (17)	−0.0131 (9)	0.0117 (11)	−0.0213 (11)
O10	0.0782 (15)	0.0666 (14)	0.0503 (11)	−0.0389 (12)	−0.0044 (10)	−0.0085 (11)

N3—C15	1.483 (3)	C9—C8	1.522 (3)
N3—H3C	0.924 (18)	C4—C3	1.381 (3)
N3—H3A	0.89 (3)	C4—H4	0.9300
N3—H3B	0.86 (3)	C3—H3	0.9300
Cd1—N1	2.2185 (16)	C14—O8	1.246 (3)
Cd1—N2	2.2236 (17)	C14—C13	1.517 (3)
Cd1—O7	2.2906 (16)	C13—C12	1.382 (3)
Cd1—O1	2.364 (2)	N4—C16	1.490 (3)
Cd1—O3	2.3965 (18)	N4—H4C	0.91 (3)
Cd1—O5	2.4197 (18)	N4—H4B	0.83 (3)
O2—C1	1.252 (3)	N4—H4A	0.91 (3)
O1—C1	1.251 (3)	C16—C17	1.515 (3)
C2—N1	1.333 (3)	C16—C15	1.518 (3)
C2—C3	1.388 (3)	C16—H16	0.9800
C2—C1	1.517 (3)	C12—C11	1.376 (4)
N1—C6	1.334 (3)	C12—H12	0.9300
C6—C5	1.383 (3)	C15—H15A	0.9700
C6—C7	1.522 (3)	C15—H15B	0.9700
O5—C8	1.268 (3)	C11—C10	1.384 (4)
O3—C7	1.266 (3)	C11—H11	0.9300
O7—C14	1.257 (3)	C10—H10	0.9300
N2—C9	1.334 (3)	C17—H17A	0.9600
N2—C13	1.335 (3)	C17—H17B	0.9600
O4—C7	1.231 (3)	C17—H17C	0.9600
O6—C8	1.234 (3)	O9—H9A	0.76 (4)
C5—C4	1.384 (3)	O9—H9B	0.84 (4)
C5—H5	0.9300	O10—H10B	0.74 (4)
C9—C10	1.387 (3)	O10—H10A	0.88 (6)
C15—N3—H3C	112.1 (19)	C4—C3—H3	120.7
C15—N3—H3A	107.1 (19)	C2—C3—H3	120.7
H3C—N3—H3A	107 (3)	O4—C7—O3	126.7 (2)
C15—N3—H3B	111 (2)	O4—C7—C6	116.74 (19)
H3C—N3—H3B	110 (3)	O3—C7—C6	116.52 (18)
H3A—N3—H3B	110 (3)	O8—C14—O7	124.7 (2)
N1—Cd1—N2	160.33 (6)	O8—C14—C13	117.2 (2)
N1—Cd1—O7	126.63 (6)	O7—C14—C13	118.04 (18)
N2—Cd1—O7	72.61 (6)	N2—C13—C12	120.8 (2)
N1—Cd1—O1	71.23 (7)	N2—C13—C14	114.95 (17)
N2—Cd1—O1	110.88 (7)	C12—C13—C14	124.22 (19)
O7—Cd1—O1	103.92 (7)	O6—C8—O5	126.1 (2)
N1—Cd1—O3	70.42 (6)	O6—C8—C9	117.6 (2)
N2—Cd1—O3	110.59 (7)	O5—C8—C9	116.27 (19)
O7—Cd1—O3	86.77 (6)	C16—N4—H4C	107.8 (18)
O1—Cd1—O3	138.50 (6)	C16—N4—H4B	108 (2)
N1—Cd1—O5	90.60 (6)	H4C—N4—H4B	113 (3)
N2—Cd1—O5	70.02 (6)	C16—N4—H4A	108.2 (19)
O7—Cd1—O5	142.62 (6)	H4C—N4—H4A	111 (3)
O1—Cd1—O5	90.16 (7)	H4B—N4—H4A	109 (3)
O3—Cd1—O5	105.44 (6)	N4—C16—C17	109.4 (2)
C1—O1—Cd1	115.64 (14)	N4—C16—C15	108.95 (18)
N1—C2—C3	120.81 (19)	C17—C16—C15	114.1 (2)
N1—C2—C1	115.44 (17)	N4—C16—H16	108.1
C3—C2—C1	123.71 (18)	C17—C16—H16	108.1
C2—N1—C6	121.19 (17)	C15—C16—H16	108.1
C2—N1—Cd1	118.94 (13)	C11—C12—C13	118.8 (2)
C6—N1—Cd1	119.73 (13)	C11—C12—H12	120.6
N1—C6—C5	120.86 (19)	C13—C12—H12	120.6
N1—C6—C7	115.26 (17)	N3—C15—C16	110.77 (19)
C5—C6—C7	123.83 (19)	N3—C15—H15A	109.5
C8—O5—Cd1	116.58 (14)	C16—C15—H15A	109.5
O1—C1—O2	126.0 (2)	N3—C15—H15B	109.5
O1—C1—C2	117.64 (18)	C16—C15—H15B	109.5
O2—C1—C2	116.35 (18)	H15A—C15—H15B	108.1
C7—O3—Cd1	114.43 (12)	C12—C11—C10	120.0 (2)
C14—O7—Cd1	116.65 (14)	C12—C11—H11	120.0
C9—N2—C13	121.17 (18)	C10—C11—H11	120.0
C9—N2—Cd1	121.10 (14)	C11—C10—C9	118.5 (2)
C13—N2—Cd1	117.70 (14)	C11—C10—H10	120.8
C6—C5—C4	118.7 (2)	C9—C10—H10	120.8
C6—C5—H5	120.6	C16—C17—H17A	109.5
C4—C5—H5	120.6	C16—C17—H17B	109.5
N2—C9—C10	120.7 (2)	H17A—C17—H17B	109.5
N2—C9—C8	116.00 (18)	C16—C17—H17C	109.5
C10—C9—C8	123.3 (2)	H17A—C17—H17C	109.5
C3—C4—C5	119.84 (19)	H17B—C17—H17C	109.5
C3—C4—H4	120.1	H9A—O9—H9B	104 (4)
C5—C4—H4	120.1	H10B—O10—H10A	106 (4)
C4—C3—C2	118.59 (19)
N1—Cd1—O1—C1	9.37 (15)	O3—Cd1—N2—C9	−100.88 (15)
N2—Cd1—O1—C1	−149.82 (15)	O5—Cd1—N2—C9	−1.33 (15)
O7—Cd1—O1—C1	133.77 (16)	N1—Cd1—N2—C13	170.20 (16)
O3—Cd1—O1—C1	32.7 (2)	O7—Cd1—N2—C13	1.35 (14)
O5—Cd1—O1—C1	−81.21 (16)	O1—Cd1—N2—C13	−97.29 (15)
C3—C2—N1—C6	0.3 (3)	O3—Cd1—N2—C13	80.95 (15)
C1—C2—N1—C6	−177.55 (17)	O5—Cd1—N2—C13	−179.50 (16)
C3—C2—N1—Cd1	−175.32 (14)	N1—C6—C5—C4	0.3 (3)
C1—C2—N1—Cd1	6.9 (2)	C7—C6—C5—C4	−177.21 (19)
N2—Cd1—N1—C2	91.3 (2)	C13—N2—C9—C10	−0.2 (3)
O7—Cd1—N1—C2	−101.95 (15)	Cd1—N2—C9—C10	−178.30 (16)
O1—Cd1—N1—C2	−8.29 (14)	C13—N2—C9—C8	179.24 (18)
O3—Cd1—N1—C2	−172.14 (16)	Cd1—N2—C9—C8	1.1 (2)
O5—Cd1—N1—C2	81.67 (15)	C6—C5—C4—C3	−0.1 (3)
N2—Cd1—N1—C6	−84.3 (2)	C5—C4—C3—C2	−0.1 (3)
O7—Cd1—N1—C6	82.38 (16)	N1—C2—C3—C4	0.0 (3)
O1—Cd1—N1—C6	176.04 (16)	C1—C2—C3—C4	177.62 (19)
O3—Cd1—N1—C6	12.20 (13)	Cd1—O3—C7—O4	−160.3 (2)
O5—Cd1—N1—C6	−93.99 (15)	Cd1—O3—C7—C6	19.5 (2)
C2—N1—C6—C5	−0.4 (3)	N1—C6—C7—O4	170.5 (2)
Cd1—N1—C6—C5	175.12 (15)	C5—C6—C7—O4	−11.9 (3)
C2—N1—C6—C7	177.30 (17)	N1—C6—C7—O3	−9.4 (3)
Cd1—N1—C6—C7	−7.1 (2)	C5—C6—C7—O3	168.28 (19)
N1—Cd1—O5—C8	178.02 (17)	Cd1—O7—C14—O8	176.57 (18)
N2—Cd1—O5—C8	1.47 (16)	Cd1—O7—C14—C13	−1.5 (3)
O7—Cd1—O5—C8	2.8 (2)	C9—N2—C13—C12	0.2 (3)
O1—Cd1—O5—C8	−110.75 (17)	Cd1—N2—C13—C12	178.42 (15)
O3—Cd1—O5—C8	108.19 (17)	C9—N2—C13—C14	179.35 (18)
Cd1—O1—C1—O2	170.55 (18)	Cd1—N2—C13—C14	−2.5 (2)
Cd1—O1—C1—C2	−9.2 (2)	O8—C14—C13—N2	−175.54 (19)
N1—C2—C1—O1	2.1 (3)	O7—C14—C13—N2	2.6 (3)
C3—C2—C1—O1	−175.7 (2)	O8—C14—C13—C12	3.5 (3)
N1—C2—C1—O2	−177.69 (19)	O7—C14—C13—C12	−178.3 (2)
C3—C2—C1—O2	4.6 (3)	Cd1—O5—C8—O6	177.91 (19)
N1—Cd1—O3—C7	−17.16 (14)	Cd1—O5—C8—C9	−1.4 (2)
N2—Cd1—O3—C7	141.91 (15)	N2—C9—C8—O6	−179.1 (2)
O7—Cd1—O3—C7	−148.03 (15)	C10—C9—C8—O6	0.3 (3)
O1—Cd1—O3—C7	−40.58 (19)	N2—C9—C8—O5	0.3 (3)
O5—Cd1—O3—C7	67.86 (15)	C10—C9—C8—O5	179.7 (2)
N1—Cd1—O7—C14	−175.19 (15)	N2—C13—C12—C11	−0.3 (3)
N2—Cd1—O7—C14	0.15 (15)	C14—C13—C12—C11	−179.3 (2)
O1—Cd1—O7—C14	108.04 (17)	N4—C16—C15—N3	167.86 (18)
O3—Cd1—O7—C14	−112.60 (17)	C17—C16—C15—N3	−69.6 (3)
O5—Cd1—O7—C14	−1.2 (2)	C13—C12—C11—C10	0.3 (4)
N1—Cd1—N2—C9	−11.6 (3)	C12—C11—C10—C9	−0.3 (4)
O7—Cd1—N2—C9	179.53 (17)	N2—C9—C10—C11	0.2 (3)
O1—Cd1—N2—C9	80.88 (16)	C8—C9—C10—C11	−179.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O10i	0.89 (3)	1.90 (3)	2.780 (3)	172 (3)
N3—H3B···O3ii	0.86 (3)	2.04 (3)	2.899 (3)	177 (3)
N3—H3C···O2i	0.92 (2)	1.89 (2)	2.790 (3)	164 (3)
N4—H4A···O8ii	0.91 (3)	1.96 (3)	2.870 (3)	176 (3)
N4—H4B···O5	0.83 (3)	2.06 (3)	2.889 (3)	172 (3)
N4—H4C···O9ii	0.91 (3)	1.90 (3)	2.803 (3)	170 (3)
O9—H9A···O4iii	0.76 (4)	1.96 (4)	2.708 (3)	170 (4)
O9—H9B···O2iv	0.84 (4)	2.00 (4)	2.827 (3)	165 (4)
O10—H10A···O6v	0.88 (6)	2.04 (6)	2.848 (4)	151 (6)
O10—H10B···O8vi	0.74 (4)	2.19 (4)	2.835 (3)	147 (4)
C10—H10···O3vii	0.93	2.54	3.298 (3)	139
C12—H12···O1vi	0.93	2.44	3.200 (3)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O10i	0.89 (3)	1.90 (3)	2.780 (3)	172 (3)
N3—H3B⋯O3ii	0.86 (3)	2.04 (3)	2.899 (3)	177 (3)
N3—H3C⋯O2i	0.92 (2)	1.89 (2)	2.790 (3)	164 (3)
N4—H4A⋯O8ii	0.91 (3)	1.96 (3)	2.870 (3)	176 (3)
N4—H4B⋯O5	0.83 (3)	2.06 (3)	2.889 (3)	172 (3)
N4—H4C⋯O9ii	0.91 (3)	1.90 (3)	2.803 (3)	170 (3)
O9—H9A⋯O4iii	0.76 (4)	1.96 (4)	2.708 (3)	170 (4)
O9—H9B⋯O2iv	0.84 (4)	2.00 (4)	2.827 (3)	165 (4)
O10—H10A⋯O6v	0.88 (6)	2.04 (6)	2.848 (4)	151 (6)
O10—H10B⋯O8vi	0.74 (4)	2.19 (4)	2.835 (3)	147 (4)
C10—H10⋯O3vii	0.93	2.54	3.298 (3)	139
C12—H12⋯O1vi	0.93	2.44	3.200 (3)	139

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