Butane-1,4-diammonium bis-(pyridine-2,6-dicarboxyl-ato-κO,N,O)cadmate(II) dihydrate.

In the title compound, (C(4)H(14)N(2))[Cd(C(7)H(3)NO(4))(2)]·2H(2)O, the Cd(II) ion is coordinated by four O atoms [Cd-O = 2.2399 (17)-2.2493 (17) Å] and two N atoms [Cd-N = 2.3113 (15) and 2.3917 (15) Å] from two tridentate pyridine-2,6-dicarboxyl-ato ligands in a distorted octa-hedral geometry. The uncoordinated water mol-ecules are involved in O-H⋯O and N-H⋯O hydrogen bonds, which contribute to the formation of a three-dimensional supra-molecular structure, along with π-π stacking inter-actions [centroid-centroid distances of 3.5313 (13) and 3.6028 (11) Å between the pyridine rings of neighbouring dianions].

Related literature

For related literature, see: Aghabozorg, Firoozi et al. (2008 ▶); Aghabozorg, Manteghi et al. (2008 ▶); Odoko et al. (2002 ▶).

Experimental

Crystal data

(C4H14N2)[n class="Chemical">Cd(C7H3NO4)2]·2H2O

M = 568.81

Monoclinic,

a = 11.0357 (4) Å

b = 28.7181 (10) Å

c = 7.1116 (3) Å

β = 108.544 (1)°

V = 2136.82 (14) Å3

Z = 4

Mo Kα radiation

μ = 1.09 mm−1

T = 100 (2) K

0.28 × 0.07 × 0.05 mm

Data collection

Bruker SMART APEXII CCD area detector diffractometer

Absorption correction: multi-scan (APEX2; Bruker, 2005 ▶) T min = 0.802, T max = 0.944

25988 measured reflections

5676 independent reflections

4655 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.066

S = 0.99

5676 reflections

298 parameters

H-atom parameters constrained

Δρmax = 0.59 e Å−3

Δρmin = −0.71 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808029395/cv2442sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029395/cv2442Isup2.hkl

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

(C4H14N2)[Cd(C7H3NO4)2]·2H2O	F(000) = 1152
Mr = 568.81	Dx = 1.768 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6372 reflections
a = 11.0357 (4) Å	θ = 2.8–32.1°
b = 28.7181 (10) Å	µ = 1.09 mm−1
c = 7.1116 (3) Å	T = 100 K
β = 108.544 (1)°	Prism, colourless
V = 2136.82 (14) Å3	0.28 × 0.07 × 0.05 mm
Z = 4

Bruker SMART APEX II CCD area detector diffractometer	5676 independent reflections
Radiation source: fine-focus sealed tube	4655 reflections with I > 2σ(I)
graphite	Rint = 0.044
phi and ω scans	θmax = 29.0°, θmin = 2.0°
Absorption correction: multi-scan (APEX2; Bruker, 2005)	h = −15→15
Tmin = 0.802, Tmax = 0.944	k = −39→39
25988 measured reflections	l = −9→9

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)] = 0.027	Hydrogen site location: mixed
wR(F2) = 0.066	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0369P)2 + 0.2951P] where P = (Fo2 + 2Fc2)/3
5676 reflections	(Δ/σ)max = 0.001
298 parameters	Δρmax = 0.59 e Å−3
0 restraints	Δρmin = −0.71 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	0.653305 (14)	0.865460 (5)	0.02554 (2)	0.01027 (5)
O1	0.54740 (15)	0.88396 (5)	0.2485 (2)	0.0163 (3)
O2	0.49107 (15)	0.94185 (5)	0.4137 (2)	0.0177 (3)
O3	0.74579 (14)	0.90014 (5)	−0.1942 (2)	0.0133 (3)
O4	0.80812 (14)	0.96709 (5)	−0.2947 (2)	0.0148 (3)
O5	0.46311 (14)	0.83512 (5)	−0.1895 (2)	0.0130 (3)
O6	0.35049 (14)	0.77036 (5)	−0.2989 (2)	0.0134 (3)
O7	0.85227 (14)	0.84106 (5)	0.2568 (2)	0.0135 (3)
O8	0.97512 (14)	0.77840 (5)	0.3736 (2)	0.0140 (3)
N1	0.66045 (16)	0.94278 (6)	0.0692 (2)	0.0107 (3)
N2	0.66196 (16)	0.78722 (6)	0.0372 (2)	0.0094 (3)
C1	0.61249 (19)	0.96095 (7)	0.2039 (3)	0.0106 (4)
C2	0.6181 (2)	1.00835 (7)	0.2422 (3)	0.0130 (4)
H2A	0.5863	1.0207	0.3381	0.016*
C3	0.6726 (2)	1.03710 (7)	0.1332 (3)	0.0144 (4)
H3A	0.6780	1.0690	0.1560	0.017*
C4	0.7193 (2)	1.01781 (7)	−0.0105 (3)	0.0137 (4)
H4A	0.7546	1.0366	−0.0861	0.016*
C5	0.71190 (19)	0.96990 (7)	−0.0379 (3)	0.0106 (4)
C6	0.5459 (2)	0.92595 (7)	0.2994 (3)	0.0119 (4)
C7	0.75859 (19)	0.94381 (7)	−0.1888 (3)	0.0108 (4)
C8	0.56098 (19)	0.76257 (7)	−0.0730 (3)	0.0096 (4)
C9	0.5627 (2)	0.71438 (7)	−0.0708 (3)	0.0119 (4)
H9A	0.4929	0.6975	−0.1489	0.014*
C10	0.67082 (19)	0.69158 (7)	0.0503 (3)	0.0120 (4)
H10A	0.6738	0.6592	0.0553	0.014*
C11	0.7742 (2)	0.71772 (7)	0.1635 (3)	0.0117 (4)
H11A	0.8473	0.7032	0.2451	0.014*
C12	0.76656 (19)	0.76590 (7)	0.1527 (3)	0.0100 (4)
C13	0.44812 (19)	0.79128 (7)	−0.1984 (3)	0.0106 (4)
C14	0.87469 (19)	0.79762 (7)	0.2713 (3)	0.0108 (4)
N3	−0.04463 (17)	0.90758 (6)	0.5575 (2)	0.0125 (3)
H3NA	0.0079	0.9221	0.5045	0.019*
H3NB	−0.0818	0.8834	0.4763	0.019*
H3NC	−0.1029	0.9278	0.5727	0.019*
N4	0.20003 (17)	0.80268 (6)	1.2890 (3)	0.0129 (4)
H4NA	0.1477	0.7916	1.3553	0.019*
H4NB	0.2523	0.7791	1.2663	0.019*
H4NC	0.2430	0.8260	1.3538	0.019*
C15	0.0263 (2)	0.89086 (8)	0.7619 (3)	0.0140 (4)
H15B	−0.0345	0.8793	0.8238	0.017*
H15C	0.0716	0.9169	0.8404	0.017*
C16	0.1212 (2)	0.85258 (8)	0.7631 (3)	0.0131 (4)
H16B	0.1777	0.8631	0.6915	0.016*
H16C	0.0753	0.8255	0.6947	0.016*
C17	0.2010 (2)	0.83878 (8)	0.9735 (3)	0.0137 (4)
H17A	0.2623	0.8152	0.9671	0.016*
H17B	0.2482	0.8657	1.0409	0.016*
C18	0.11864 (19)	0.82013 (8)	1.0923 (3)	0.0130 (4)
H18A	0.0632	0.8447	1.1110	0.016*
H18B	0.0652	0.7950	1.0195	0.016*
O1W	0.32860 (14)	0.88159 (5)	0.4844 (2)	0.0142 (3)
H1WA	0.3663	0.8704	0.5821	0.021*
H1WB	0.3741	0.8990	0.4520	0.021*
O2W	0.12203 (15)	0.94242 (6)	0.3694 (2)	0.0211 (4)
H2WA	0.1440	0.9692	0.3542	0.032*
H2WB	0.1883	0.9273	0.4046	0.032*

	U11	U22	U33	U12	U13	U23
Cd1	0.01105 (8)	0.00794 (7)	0.01223 (8)	−0.00025 (6)	0.00430 (5)	−0.00009 (6)
O1	0.0229 (8)	0.0108 (7)	0.0201 (8)	0.0005 (6)	0.0135 (7)	0.0013 (6)
O2	0.0222 (8)	0.0159 (8)	0.0205 (8)	−0.0007 (6)	0.0148 (7)	0.0002 (6)
O3	0.0156 (7)	0.0113 (7)	0.0159 (7)	−0.0016 (6)	0.0091 (6)	−0.0021 (6)
O4	0.0179 (8)	0.0141 (8)	0.0159 (7)	−0.0007 (6)	0.0102 (6)	0.0015 (6)
O5	0.0121 (7)	0.0112 (7)	0.0144 (7)	0.0005 (6)	0.0025 (6)	0.0019 (6)
O6	0.0105 (7)	0.0154 (8)	0.0126 (7)	−0.0021 (6)	0.0012 (6)	−0.0001 (6)
O7	0.0126 (7)	0.0115 (7)	0.0144 (7)	−0.0007 (6)	0.0015 (6)	−0.0006 (6)
O8	0.0094 (7)	0.0175 (8)	0.0138 (7)	0.0000 (6)	0.0017 (6)	0.0019 (6)
N1	0.0109 (8)	0.0102 (8)	0.0118 (8)	0.0001 (6)	0.0048 (7)	0.0001 (6)
N2	0.0100 (8)	0.0106 (8)	0.0079 (8)	0.0002 (6)	0.0033 (6)	−0.0012 (6)
C1	0.0101 (9)	0.0128 (10)	0.0089 (9)	0.0011 (8)	0.0030 (7)	0.0005 (8)
C2	0.0135 (10)	0.0135 (10)	0.0126 (10)	−0.0012 (8)	0.0051 (8)	−0.0041 (8)
C3	0.0179 (11)	0.0110 (10)	0.0161 (10)	−0.0017 (8)	0.0080 (8)	−0.0017 (8)
C4	0.0141 (10)	0.0130 (10)	0.0152 (10)	−0.0025 (8)	0.0062 (8)	0.0007 (8)
C5	0.0095 (9)	0.0122 (10)	0.0108 (9)	0.0000 (7)	0.0042 (7)	0.0006 (7)
C6	0.0134 (10)	0.0120 (10)	0.0100 (9)	0.0006 (8)	0.0034 (8)	0.0029 (8)
C7	0.0094 (9)	0.0116 (10)	0.0115 (9)	−0.0002 (7)	0.0035 (8)	−0.0013 (7)
C8	0.0099 (10)	0.0123 (10)	0.0082 (9)	−0.0004 (7)	0.0050 (7)	0.0016 (7)
C9	0.0138 (10)	0.0121 (10)	0.0110 (9)	−0.0015 (8)	0.0059 (8)	−0.0005 (8)
C10	0.0160 (11)	0.0092 (9)	0.0122 (10)	0.0005 (8)	0.0066 (8)	0.0002 (7)
C11	0.0118 (10)	0.0133 (10)	0.0109 (9)	0.0036 (8)	0.0046 (8)	0.0030 (8)
C12	0.0102 (9)	0.0129 (10)	0.0078 (9)	0.0002 (7)	0.0040 (7)	0.0006 (7)
C13	0.0104 (10)	0.0134 (10)	0.0091 (9)	0.0009 (8)	0.0045 (8)	0.0013 (7)
C14	0.0111 (10)	0.0135 (10)	0.0091 (9)	−0.0017 (8)	0.0050 (8)	−0.0005 (7)
N3	0.0126 (8)	0.0126 (9)	0.0126 (8)	−0.0006 (7)	0.0046 (7)	0.0000 (7)
N4	0.0126 (9)	0.0141 (9)	0.0121 (8)	0.0005 (7)	0.0042 (7)	0.0002 (7)
C15	0.0133 (10)	0.0181 (11)	0.0108 (10)	−0.0004 (8)	0.0042 (8)	−0.0019 (8)
C16	0.0122 (10)	0.0155 (10)	0.0126 (10)	0.0012 (8)	0.0054 (8)	0.0010 (8)
C17	0.0121 (10)	0.0159 (11)	0.0143 (10)	0.0014 (8)	0.0058 (8)	0.0010 (8)
C18	0.0093 (10)	0.0171 (11)	0.0119 (10)	0.0001 (8)	0.0023 (8)	0.0018 (8)
O1W	0.0137 (8)	0.0153 (7)	0.0135 (7)	−0.0005 (6)	0.0044 (6)	0.0037 (6)
O2W	0.0187 (8)	0.0174 (8)	0.0304 (9)	0.0010 (6)	0.0123 (7)	0.0074 (7)

Cd1—N1	2.2399 (17)	C9—H9A	0.9300
Cd1—N2	2.2493 (17)	C10—C11	1.388 (3)
Cd1—O1	2.3113 (15)	C10—H10A	0.9300
Cd1—O5	2.3370 (15)	C11—C12	1.387 (3)
Cd1—O3	2.3433 (14)	C11—H11A	0.9300
Cd1—O7	2.3917 (15)	C12—C14	1.525 (3)
O1—C6	1.261 (3)	N3—C15	1.494 (3)
O2—C6	1.244 (3)	N3—H3NA	0.8893
O3—C7	1.262 (2)	N3—H3NB	0.9137
O4—C7	1.255 (2)	N3—H3NC	0.8970
O5—C13	1.269 (2)	N4—C18	1.488 (3)
O6—C13	1.242 (2)	N4—H4NA	0.9110
O7—C14	1.269 (2)	N4—H4NB	0.9372
O8—C14	1.245 (2)	N4—H4NC	0.8628
N1—C5	1.336 (3)	C15—C16	1.517 (3)
N1—C1	1.339 (3)	C15—H15B	0.9700
N2—C12	1.334 (3)	C15—H15C	0.9700
N2—C8	1.342 (3)	C16—C17	1.528 (3)
C1—C2	1.386 (3)	C16—H16B	0.9700
C1—C6	1.526 (3)	C16—H16C	0.9700
C2—C3	1.394 (3)	C17—C18	1.521 (3)
C2—H2A	0.9300	C17—H17A	0.9700
C3—C4	1.397 (3)	C17—H17B	0.9700
C3—H3A	0.9300	C18—H18A	0.9700
C4—C5	1.388 (3)	C18—H18B	0.9700
C4—H4A	0.9300	O1W—H1WA	0.7580
C5—C7	1.526 (3)	O1W—H1WB	0.7927
C8—C9	1.384 (3)	O2W—H2WA	0.8246
C8—C13	1.523 (3)	O2W—H2WB	0.8183
C9—C10	1.393 (3)
N1—Cd1—N2	170.37 (6)	C11—C10—H10A	120.4
N1—Cd1—O1	71.35 (6)	C9—C10—H10A	120.4
N2—Cd1—O1	103.25 (6)	C12—C11—C10	118.90 (19)
N1—Cd1—O5	116.42 (6)	C12—C11—H11A	120.5
N2—Cd1—O5	70.76 (5)	C10—C11—H11A	120.5
O1—Cd1—O5	89.41 (6)	N2—C12—C11	121.14 (19)
N1—Cd1—O3	70.59 (6)	N2—C12—C14	115.98 (18)
N2—Cd1—O3	115.25 (5)	C11—C12—C14	122.87 (18)
O1—Cd1—O3	141.50 (5)	O6—C13—O5	125.73 (19)
O5—Cd1—O3	102.30 (5)	O6—C13—C8	118.25 (18)
N1—Cd1—O7	102.18 (6)	O5—C13—C8	116.01 (17)
N2—Cd1—O7	70.31 (5)	O8—C14—O7	126.69 (19)
O1—Cd1—O7	98.60 (5)	O8—C14—C12	116.93 (18)
O5—Cd1—O7	141.06 (5)	O7—C14—C12	116.37 (18)
O3—Cd1—O7	94.81 (5)	C15—N3—H3NA	110.6
C6—O1—Cd1	118.20 (13)	C15—N3—H3NB	111.2
C7—O3—Cd1	118.05 (12)	H3NA—N3—H3NB	108.0
C13—O5—Cd1	118.57 (13)	C15—N3—H3NC	105.3
C14—O7—Cd1	117.15 (13)	H3NA—N3—H3NC	109.7
C5—N1—C1	121.14 (18)	H3NB—N3—H3NC	111.9
C5—N1—Cd1	120.09 (14)	C18—N4—H4NA	108.1
C1—N1—Cd1	118.76 (13)	C18—N4—H4NB	107.6
C12—N2—C8	120.84 (18)	H4NA—N4—H4NB	111.3
C12—N2—Cd1	119.97 (13)	C18—N4—H4NC	107.8
C8—N2—Cd1	119.19 (13)	H4NA—N4—H4NC	108.9
N1—C1—C2	121.36 (19)	H4NB—N4—H4NC	112.9
N1—C1—C6	114.67 (18)	N3—C15—C16	112.65 (17)
C2—C1—C6	123.87 (18)	N3—C15—H15B	109.1
C1—C2—C3	118.22 (19)	C16—C15—H15B	109.1
C1—C2—H2A	120.9	N3—C15—H15C	109.1
C3—C2—H2A	120.9	C16—C15—H15C	109.1
C2—C3—C4	119.8 (2)	H15B—C15—H15C	107.8
C2—C3—H3A	120.1	C15—C16—C17	112.01 (17)
C4—C3—H3A	120.1	C15—C16—H16B	109.2
C5—C4—C3	118.46 (19)	C17—C16—H16B	109.2
C5—C4—H4A	120.8	C15—C16—H16C	109.2
C3—C4—H4A	120.8	C17—C16—H16C	109.2
N1—C5—C4	120.96 (19)	H16B—C16—H16C	107.9
N1—C5—C7	114.49 (18)	C18—C17—C16	112.08 (17)
C4—C5—C7	124.55 (18)	C18—C17—H17A	109.2
O2—C6—O1	126.3 (2)	C16—C17—H17A	109.2
O2—C6—C1	116.86 (18)	C18—C17—H17B	109.2
O1—C6—C1	116.76 (18)	C16—C17—H17B	109.2
O4—C7—O3	125.23 (19)	H17A—C17—H17B	107.9
O4—C7—C5	118.00 (18)	N4—C18—C17	110.61 (17)
O3—C7—C5	116.76 (17)	N4—C18—H18A	109.5
N2—C8—C9	120.98 (18)	C17—C18—H18A	109.5
N2—C8—C13	115.40 (17)	N4—C18—H18B	109.5
C9—C8—C13	123.63 (18)	C17—C18—H18B	109.5
C8—C9—C10	118.89 (19)	H18A—C18—H18B	108.1
C8—C9—H9A	120.6	H1WA—O1W—H1WB	108.6
C10—C9—H9A	120.6	H2WA—O2W—H2WB	105.3
C11—C10—C9	119.24 (19)
N1—Cd1—O1—C6	−3.07 (15)	C1—N1—C5—C7	−178.33 (17)
N2—Cd1—O1—C6	168.63 (15)	Cd1—N1—C5—C7	1.7 (2)
O5—Cd1—O1—C6	−121.31 (16)	C3—C4—C5—N1	0.5 (3)
O3—Cd1—O1—C6	−12.1 (2)	C3—C4—C5—C7	179.94 (19)
O7—Cd1—O1—C6	96.96 (16)	Cd1—O1—C6—O2	178.27 (17)
N1—Cd1—O3—C7	0.66 (14)	Cd1—O1—C6—C1	1.3 (2)
N2—Cd1—O3—C7	−171.05 (14)	N1—C1—C6—O2	−174.47 (18)
O1—Cd1—O3—C7	9.71 (18)	C2—C1—C6—O2	2.0 (3)
O5—Cd1—O3—C7	114.61 (14)	N1—C1—C6—O1	2.8 (3)
O7—Cd1—O3—C7	−100.58 (14)	C2—C1—C6—O1	179.3 (2)
N1—Cd1—O5—C13	−170.64 (14)	Cd1—O3—C7—O4	178.78 (16)
N2—Cd1—O5—C13	2.38 (14)	Cd1—O3—C7—C5	0.0 (2)
O1—Cd1—O5—C13	−101.88 (14)	N1—C5—C7—O4	−179.97 (18)
O3—Cd1—O5—C13	115.11 (14)	C4—C5—C7—O4	0.6 (3)
O7—Cd1—O5—C13	1.14 (18)	N1—C5—C7—O3	−1.1 (3)
N1—Cd1—O7—C14	177.80 (14)	C4—C5—C7—O3	179.49 (19)
N2—Cd1—O7—C14	4.07 (14)	C12—N2—C8—C9	−0.4 (3)
O1—Cd1—O7—C14	105.15 (14)	Cd1—N2—C8—C9	179.68 (14)
O5—Cd1—O7—C14	5.33 (18)	C12—N2—C8—C13	−179.87 (17)
O3—Cd1—O7—C14	−111.05 (14)	Cd1—N2—C8—C13	0.2 (2)
O1—Cd1—N1—C5	−175.36 (16)	N2—C8—C9—C10	0.9 (3)
O5—Cd1—N1—C5	−95.72 (15)	C13—C8—C9—C10	−179.67 (18)
O3—Cd1—N1—C5	−1.29 (14)	C8—C9—C10—C11	−0.7 (3)
O7—Cd1—N1—C5	89.55 (15)	C9—C10—C11—C12	0.1 (3)
O1—Cd1—N1—C1	4.68 (14)	C8—N2—C12—C11	−0.3 (3)
O5—Cd1—N1—C1	84.32 (15)	Cd1—N2—C12—C11	179.66 (14)
O3—Cd1—N1—C1	178.74 (16)	C8—N2—C12—C14	−179.80 (17)
O7—Cd1—N1—C1	−90.41 (15)	Cd1—N2—C12—C14	0.1 (2)
O1—Cd1—N2—C12	−96.51 (15)	C10—C11—C12—N2	0.4 (3)
O5—Cd1—N2—C12	178.85 (16)	C10—C11—C12—C14	179.90 (18)
O3—Cd1—N2—C12	83.98 (15)	Cd1—O5—C13—O6	176.78 (16)
O7—Cd1—N2—C12	−1.98 (14)	Cd1—O5—C13—C8	−3.1 (2)
O1—Cd1—N2—C8	83.43 (15)	N2—C8—C13—O6	−177.92 (17)
O5—Cd1—N2—C8	−1.21 (13)	C9—C8—C13—O6	2.6 (3)
O3—Cd1—N2—C8	−96.08 (14)	N2—C8—C13—O5	1.9 (3)
O7—Cd1—N2—C8	177.96 (16)	C9—C8—C13—O5	−177.53 (19)
C5—N1—C1—C2	−2.2 (3)	Cd1—O7—C14—O8	175.41 (16)
Cd1—N1—C1—C2	177.80 (15)	Cd1—O7—C14—C12	−5.4 (2)
C5—N1—C1—C6	174.40 (18)	N2—C12—C14—O8	−177.06 (17)
Cd1—N1—C1—C6	−5.6 (2)	C11—C12—C14—O8	3.4 (3)
N1—C1—C2—C3	1.4 (3)	N2—C12—C14—O7	3.6 (3)
C6—C1—C2—C3	−174.79 (19)	C11—C12—C14—O7	−175.88 (19)
C1—C2—C3—C4	0.2 (3)	N3—C15—C16—C17	175.10 (17)
C2—C3—C4—C5	−1.2 (3)	C15—C16—C17—C18	61.0 (2)
C1—N1—C5—C4	1.1 (3)	C16—C17—C18—N4	174.37 (17)
Cd1—N1—C5—C4	−178.82 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3NA···O2W	0.89	1.90	2.782 (2)	169
N3—H3NB···O7i	0.91	1.93	2.823 (2)	166
N3—H3NC···O4ii	0.90	1.93	2.784 (2)	159
N4—H4NA···O8ii	0.91	1.99	2.821 (3)	152
N4—H4NB···O6iii	0.94	1.93	2.865 (2)	176
N4—H4NC···O1Wiv	0.86	1.94	2.797 (2)	175
O1W—H1WA···O5iv	0.76	1.92	2.678 (2)	173
O1W—H1WB···O2	0.79	1.87	2.653 (2)	172
O2W—H2WA···O4v	0.82	1.99	2.809 (2)	175
O2W—H2WB···O1W	0.82	1.97	2.781 (2)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3NA⋯O2W	0.89	1.90	2.782 (2)	169
N3—H3NB⋯O7i	0.91	1.93	2.823 (2)	166
N3—H3NC⋯O4ii	0.90	1.93	2.784 (2)	159
N4—H4NA⋯O8ii	0.91	1.99	2.821 (3)	152
N4—H4NB⋯O6iii	0.94	1.93	2.865 (2)	176
N4—H4NC⋯O1Wiv	0.86	1.94	2.797 (2)	175
O1W—H1WA⋯O5iv	0.76	1.92	2.678 (2)	173
O1W—H1WB⋯O2	0.79	1.87	2.653 (2)	172
O2W—H2WA⋯O4v	0.82	1.99	2.809 (2)	175
O2W—H2WB⋯O1W	0.82	1.97	2.781 (2)	170

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