catena-Poly[[aqua-bis-(4-formyl-benzoato-κ(2) O (1),O (1'))cadmium]-μ-pyrazine-κ(2) N:N'].

The polymeric title compound, [Cd(C8H5O3)2(C4H4N2)(H2O)] n , contains two 4-formyl-benzoate (FB) anions, one pyrazine mol-ecule and one coordinating water mol-ecule; the FB anions act as bidentate ligands. The O atom, the aldehyde H atom and the benzene ring of one of the FB anions are disordered over two positions. The O atoms were freely refined [refined occupancy ratio 0.79 (2):0.21 (2)], while the aldehyde H atoms and the benzene ring atoms were refined with fixed occupancy ratios of 0.8:0.2 and 0.5:0.5, respectively. In the ordered FB anion, the carboxyl-ate group is twisted away from the attached benzene ring (A) by 22.7 (8)°. In the disordered FB anion, the corresponding angles are 15.6 (10) and 11.4 (11)° for rings B and B', respectively. Benzene rings A and B are oriented at a dihedral angle of 24.2 (7), A and B' at 43.0 (8)°. The pyrazine ring makes dihedral angles of 67.5 (4), 89.6 (7) and 86.2 (7)°, respectively, with benzene rings A, B and B'. The pyrazine ligands bridge the Cd(II) cations, forming polymeric chains running along the b-axis direction. In the crystal, O-Hwater ⋯ Ocarboxyl-ate hydrogen bonds link adjacent chains into layers parallel to the bc plane. These layers are linked via C-Hpyrazine ⋯ Oform-yl hydrogen bonds, forming a three-dimensional network. π-π interactions [centroid-centroid distances = 3.870 (11)-3.951 (5) Å] further stabilize the crystal structure. There is also a weak C-H⋯π inter-action present.

Related literature

For structural functions and coordination relationships of the aryl­carboxyl­ate ion in transition metal complexes of benzoic acid derivatives, see: Nadzhafov et al. (1981 ▶); Shnulin et al. (1981 ▶). For applications of transition metal complexes with biochemical mol­ecules in biological systems, see: Antolini et al. (1982 ▶). Some benzoic acid derivatives such as 4-amino­benzoic acid have been extensively reported in coordination chemistry, as bifunctional organic ligands, due to the varieties of their coordination modes, see: Chen & Chen (2002 ▶); Amiraslanov et al. (1979 ▶); Hauptmann et al. (2000 ▶). For related structures, see: Hökelek et al. (2009 ▶); Sertçelik et al. (2013 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

[Cd(C8H5O3)2(C4H4N2)(H2O)]

M = 508.76

Monoclinic,

a = 22.6016 (5) Å

b = 7.4947 (2) Å

c = 11.9196 (3) Å

β = 99.673 (4)°

V = 1990.38 (9) Å3

Z = 4

Mo Kα radiation

μ = 1.14 mm−1

T = 294 K

0.45 × 0.35 × 0.15 mm

Data collection

Bruker SMART BREEZE CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2012 ▶) T min = 0.625, T max = 0.842

40178 measured reflections

3587 independent reflections

3497 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.144

S = 1.35

3587 reflections

287 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.77 e Å−3

Δρmin = −1.85 e Å−3

Data collection: APEX2 (Bruker, 2012 ▶); cell refinement: SAINT (Bruker, 2012 ▶); data reduction: SAINT; 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, 2012 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813035010/su2679sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813035010/su2679Isup2.hkl

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Cd(C8H5O3)2(C4H4N2)(H2O)]	F(000) = 1016
Mr = 508.76	Dx = 1.684 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9816 reflections
a = 22.6016 (5) Å	θ = 2.7–28.4°
b = 7.4947 (2) Å	µ = 1.14 mm−1
c = 11.9196 (3) Å	T = 294 K
β = 99.673 (4)°	Plate, colourless
V = 1990.38 (9) Å3	0.45 × 0.35 × 0.15 mm
Z = 4

Bruker SMART BREEZE CCD diffractometer	3587 independent reflections
Radiation source: fine-focus sealed tube	3497 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
φ and ω scans	θmax = 25.3°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −27→27
Tmin = 0.625, Tmax = 0.842	k = −8→8
40178 measured reflections	l = −14→14

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 1.35	w = 1/[σ2(Fo2) + (0.0316P)2 + 14.8406P] where P = (Fo2 + 2Fc2)/3
3587 reflections	(Δ/σ)max < 0.001
287 parameters	Δρmax = 1.77 e Å−3
3 restraints	Δρmin = −1.85 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.25229 (2)	0.17641 (6)	0.12918 (4)	0.02711 (18)
O1	0.3237 (2)	0.1914 (8)	0.2983 (4)	0.0451 (13)
O2	0.3601 (2)	0.1504 (9)	0.1430 (5)	0.0567 (16)
O3	0.6257 (4)	0.2685 (15)	0.5777 (8)	0.105 (3)
O4	0.1447 (2)	0.1687 (9)	0.0798 (5)	0.0551 (16)
O5	0.1829 (2)	0.1597 (8)	0.2594 (5)	0.0503 (15)
O6A	−0.1449 (4)	0.134 (2)	0.2280 (11)	0.124 (6)	0.79 (2)
O6B	−0.111 (2)	0.139 (9)	0.378 (6)	0.16 (3)	0.21 (2)
O7	0.2521 (2)	0.1713 (7)	−0.0625 (4)	0.0362 (11)
H71	0.263 (3)	0.278 (4)	−0.054 (7)	0.056*
H72	0.221 (2)	0.168 (9)	−0.109 (6)	0.056*
N1	0.2519 (2)	0.4797 (9)	0.1242 (4)	0.0299 (13)
N2	0.2503 (2)	0.8645 (6)	0.1216 (5)	0.0263 (11)
C1	0.3678 (3)	0.1700 (9)	0.2472 (6)	0.0330 (15)
C2	0.4297 (3)	0.1712 (9)	0.3143 (6)	0.0304 (14)
C3	0.4421 (3)	0.2522 (11)	0.4201 (6)	0.0406 (17)
H3	0.4112	0.3025	0.4521	0.049*
C4	0.5005 (4)	0.2584 (12)	0.4780 (6)	0.047 (2)
H4	0.5089	0.3158	0.5480	0.056*
C5	0.5460 (3)	0.1806 (12)	0.4330 (7)	0.047 (2)
C6	0.5336 (4)	0.0950 (14)	0.3294 (8)	0.059 (2)
H6	0.5645	0.0402	0.2996	0.071*
C7	0.4760 (3)	0.0897 (12)	0.2694 (7)	0.0452 (19)
H7	0.4681	0.0321	0.1993	0.054*
C8	0.6082 (4)	0.1889 (19)	0.4960 (10)	0.082 (4)
H8	0.6366	0.1221	0.4662	0.099*
C9	0.1387 (3)	0.1613 (9)	0.1813 (6)	0.0335 (15)
C10	0.0767 (3)	0.1475 (10)	0.2111 (6)	0.0351 (16)
C13	−0.0386 (4)	0.1296 (14)	0.2620 (8)	0.054 (2)
C11A	0.0653 (14)	0.171 (3)	0.320 (3)	0.050 (4)	0.50
H11A	0.0972	0.1880	0.3797	0.060*	0.50
C12A	0.0074 (12)	0.170 (3)	0.342 (2)	0.050 (4)	0.50
H12A	0.0005	0.1985	0.4151	0.060*	0.50
C14A	−0.0278 (12)	0.089 (3)	0.153 (2)	0.050 (4)	0.50
H14A	−0.0592	0.0529	0.0966	0.060*	0.50
C15A	0.0301 (13)	0.104 (3)	0.128 (3)	0.050 (4)	0.50
H15A	0.0369	0.0829	0.0548	0.060*	0.50
C11B	0.0702 (14)	0.106 (4)	0.319 (3)	0.057 (5)	0.50
H11B	0.1038	0.0856	0.3747	0.068*	0.50
C12B	0.0126 (12)	0.093 (3)	0.348 (2)	0.057 (5)	0.50
H12B	0.0076	0.0606	0.4208	0.068*	0.50
C14B	−0.0305 (12)	0.171 (3)	0.153 (2)	0.057 (5)	0.50
H14B	−0.0635	0.1966	0.0976	0.068*	0.50
C15B	0.0255 (13)	0.174 (3)	0.126 (3)	0.057 (5)	0.50
H15B	0.0303	0.1945	0.0515	0.068*	0.50
C16	−0.0996 (5)	0.1259 (19)	0.2908 (12)	0.081 (3)
H16A	−0.1021	0.1161	0.3677	0.097*	0.80
H16B	−0.1313	0.1104	0.2310	0.097*	0.20
C17	0.2264 (3)	0.5861 (11)	0.0310 (7)	0.0441 (18)
H17	0.2087	0.5283	−0.0352	0.053*
C18	0.2260 (3)	0.7705 (9)	0.0313 (6)	0.0391 (17)
H18	0.2080	0.8306	−0.0339	0.047*
C19	0.2755 (3)	0.7728 (10)	0.2113 (6)	0.0381 (17)
H19	0.2933	0.8340	0.2762	0.046*
C20	0.2764 (3)	0.5877 (9)	0.2121 (6)	0.0375 (16)
H20	0.2954	0.5323	0.2783	0.045*

	U11	U22	U33	U12	U13	U23
Cd1	0.0334 (3)	0.0204 (3)	0.0268 (3)	−0.00118 (19)	0.00312 (19)	−0.00010 (18)
O1	0.031 (3)	0.060 (4)	0.045 (3)	0.007 (2)	0.007 (2)	−0.010 (3)
O2	0.042 (3)	0.092 (5)	0.035 (3)	−0.008 (3)	0.002 (2)	−0.001 (3)
O3	0.068 (5)	0.147 (9)	0.084 (6)	−0.017 (5)	−0.030 (4)	0.003 (6)
O4	0.036 (3)	0.087 (5)	0.043 (3)	0.002 (3)	0.008 (2)	0.009 (3)
O5	0.034 (3)	0.071 (4)	0.045 (3)	−0.006 (3)	0.001 (2)	−0.021 (3)
O6A	0.036 (6)	0.233 (17)	0.102 (10)	0.008 (7)	0.013 (5)	0.026 (10)
O6B	0.10 (4)	0.21 (7)	0.20 (7)	0.00 (4)	0.10 (4)	0.04 (5)
O7	0.044 (3)	0.037 (3)	0.027 (2)	0.000 (2)	0.004 (2)	0.002 (2)
N1	0.010 (2)	0.068 (4)	0.011 (2)	0.000 (2)	−0.0008 (17)	−0.005 (3)
N2	0.035 (3)	0.006 (2)	0.038 (3)	0.002 (2)	0.003 (2)	−0.001 (2)
C1	0.035 (4)	0.023 (4)	0.041 (4)	−0.001 (3)	0.004 (3)	0.002 (3)
C2	0.035 (3)	0.024 (3)	0.033 (3)	−0.003 (3)	0.007 (3)	0.004 (3)
C3	0.039 (4)	0.048 (5)	0.037 (4)	0.003 (3)	0.012 (3)	−0.008 (3)
C4	0.047 (4)	0.060 (6)	0.031 (4)	−0.007 (4)	0.000 (3)	−0.006 (4)
C5	0.034 (4)	0.057 (5)	0.050 (5)	−0.001 (4)	0.001 (3)	0.010 (4)
C6	0.038 (4)	0.078 (7)	0.064 (6)	0.008 (4)	0.014 (4)	−0.006 (5)
C7	0.040 (4)	0.054 (5)	0.043 (4)	0.003 (4)	0.012 (3)	−0.008 (4)
C8	0.042 (5)	0.123 (11)	0.075 (7)	−0.004 (6)	−0.011 (5)	0.002 (7)
C9	0.037 (4)	0.021 (3)	0.042 (4)	0.001 (3)	0.006 (3)	−0.004 (3)
C10	0.034 (4)	0.035 (4)	0.034 (4)	−0.002 (3)	0.002 (3)	−0.003 (3)
C13	0.041 (4)	0.068 (6)	0.057 (5)	0.002 (4)	0.013 (4)	−0.006 (5)
C11A	0.039 (6)	0.070 (11)	0.042 (6)	0.009 (8)	0.006 (4)	0.002 (8)
C12A	0.039 (6)	0.070 (11)	0.042 (6)	0.009 (8)	0.006 (4)	0.002 (8)
C14A	0.039 (6)	0.070 (11)	0.042 (6)	0.009 (8)	0.006 (4)	0.002 (8)
C15A	0.039 (6)	0.070 (11)	0.042 (6)	0.009 (8)	0.006 (4)	0.002 (8)
C11B	0.039 (6)	0.089 (14)	0.040 (6)	0.012 (10)	0.002 (4)	0.004 (10)
C12B	0.039 (6)	0.089 (14)	0.040 (6)	0.012 (10)	0.002 (4)	0.004 (10)
C14B	0.039 (6)	0.089 (14)	0.040 (6)	0.012 (10)	0.002 (4)	0.004 (10)
C15B	0.039 (6)	0.089 (14)	0.040 (6)	0.012 (10)	0.002 (4)	0.004 (10)
C16	0.055 (7)	0.117 (10)	0.075 (7)	−0.005 (6)	0.023 (6)	0.002 (7)
C17	0.045 (4)	0.036 (4)	0.047 (4)	−0.004 (3)	−0.003 (3)	−0.013 (3)
C18	0.049 (4)	0.022 (4)	0.041 (4)	−0.005 (3)	−0.007 (3)	0.005 (3)
C19	0.056 (5)	0.026 (4)	0.030 (4)	−0.011 (3)	−0.002 (3)	0.002 (3)
C20	0.051 (4)	0.023 (4)	0.037 (4)	−0.001 (3)	0.004 (3)	0.006 (3)

Cd1—N1	2.274 (6)	C6—H6	0.9300
Cd1—O7	2.284 (5)	C7—H7	0.9300
Cd1—N2i	2.340 (5)	C8—H8	0.9300
Cd1—O1	2.364 (5)	C9—C10	1.505 (10)
Cd1—O5	2.388 (5)	C10—C15A	1.36 (3)
Cd1—O4	2.405 (5)	C10—C11B	1.36 (3)
Cd1—O2	2.423 (6)	C10—C11A	1.38 (3)
Cd1—C9	2.744 (7)	C10—C15B	1.42 (3)
Cd1—C1	2.750 (7)	C13—C12A	1.33 (3)
O1—C1	1.262 (9)	C13—C14B	1.38 (3)
O2—C1	1.234 (9)	C13—C14A	1.40 (3)
O3—C8	1.154 (14)	C13—C12B	1.44 (3)
O4—C9	1.242 (9)	C13—C16	1.475 (13)
O5—C9	1.247 (9)	C11A—C12A	1.38 (3)
O6A—C16	1.165 (15)	C11A—H11A	0.9300
O6A—H16B	0.3504	C12A—H12A	0.9300
O6B—C16	1.12 (6)	C14A—C15A	1.39 (3)
O7—H71	0.83 (2)	C14A—H14A	0.9300
O7—H72	0.82 (2)	C15A—H15A	0.9300
N1—C20	1.365 (9)	C11B—C12B	1.40 (3)
N1—C17	1.410 (10)	C11B—H11B	0.9300
N2—C19	1.318 (9)	C12B—H12B	0.9300
N2—C18	1.326 (9)	C14B—C15B	1.36 (3)
N2—Cd1ii	2.340 (5)	C14B—H14B	0.9300
C1—C2	1.491 (9)	C15B—H15B	0.9300
C2—C3	1.385 (10)	C16—H16A	0.9300
C2—C7	1.394 (10)	C16—H16B	0.9300
C3—C4	1.383 (11)	C17—C18	1.382 (11)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.368 (12)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.387 (10)
C5—C6	1.378 (12)	C19—H19	0.9300
C5—C8	1.479 (12)	C20—H20	0.9300
C6—C7	1.376 (11)
N1—Cd1—O7	89.51 (17)	C6—C7—H7	120.2
N1—Cd1—N2i	176.30 (17)	C2—C7—H7	120.2
O7—Cd1—N2i	87.02 (18)	O3—C8—C5	127.7 (12)
N1—Cd1—O1	88.49 (18)	O3—C8—H8	116.1
O7—Cd1—O1	137.71 (18)	C5—C8—H8	116.1
N2i—Cd1—O1	94.94 (19)	O4—C9—O5	121.6 (7)
N1—Cd1—O5	93.98 (19)	O4—C9—C10	119.4 (6)
O7—Cd1—O5	139.32 (18)	O5—C9—C10	119.0 (6)
N2i—Cd1—O5	87.8 (2)	O4—C9—Cd1	61.2 (4)
O1—Cd1—O5	82.94 (17)	O5—C9—Cd1	60.4 (4)
N1—Cd1—O4	91.1 (2)	C10—C9—Cd1	178.3 (5)
O7—Cd1—O4	85.57 (18)	C15A—C10—C11B	116 (2)
N2i—Cd1—O4	87.4 (2)	C15A—C10—C11A	118.0 (17)
O1—Cd1—O4	136.69 (18)	C11B—C10—C15B	120.2 (17)
O5—Cd1—O4	53.88 (18)	C11A—C10—C15B	113.1 (19)
N1—Cd1—O2	94.7 (2)	C15A—C10—C9	119.1 (14)
O7—Cd1—O2	84.23 (18)	C11B—C10—C9	119.6 (14)
N2i—Cd1—O2	86.3 (2)	C11A—C10—C9	122.9 (15)
O1—Cd1—O2	53.89 (17)	C15B—C10—C9	120.3 (14)
O5—Cd1—O2	135.59 (18)	C12A—C13—C14B	114.6 (19)
O4—Cd1—O2	168.3 (2)	C12A—C13—C14A	119.0 (16)
N1—Cd1—C9	92.74 (18)	C14B—C13—C12B	119.6 (15)
O7—Cd1—C9	112.4 (2)	C14A—C13—C12B	112.0 (17)
N2i—Cd1—C9	87.41 (19)	C12A—C13—C16	119.1 (14)
O1—Cd1—C9	109.87 (19)	C14B—C13—C16	120.2 (14)
O5—Cd1—C9	26.99 (19)	C14A—C13—C16	122.0 (14)
O4—Cd1—C9	26.9 (2)	C12B—C13—C16	120.2 (14)
O2—Cd1—C9	161.8 (2)	C12A—C11A—C10	121 (2)
N1—Cd1—C1	91.69 (18)	C12A—C11A—H11A	119.5
O7—Cd1—C1	110.7 (2)	C10—C11A—H11A	119.5
N2i—Cd1—C1	90.73 (19)	C13—C12A—C11A	121.2 (19)
O1—Cd1—C1	27.25 (19)	C13—C12A—H12A	119.4
O5—Cd1—C1	109.70 (19)	C11A—C12A—H12A	119.4
O4—Cd1—C1	163.5 (2)	C15A—C14A—C13	119.6 (18)
O2—Cd1—C1	26.64 (19)	C15A—C14A—H14A	120.2
C9—Cd1—C1	136.7 (2)	C13—C14A—H14A	120.2
C1—O1—Cd1	93.7 (4)	C10—C15A—C14A	121 (2)
C1—O2—Cd1	91.7 (4)	C10—C15A—H15A	119.6
C9—O4—Cd1	91.9 (4)	C14A—C15A—H15A	119.6
C9—O5—Cd1	92.6 (4)	C10—C11B—C12B	120 (2)
Cd1—O7—H71	85 (6)	C10—C11B—H11B	120.1
Cd1—O7—H72	123 (6)	C12B—C11B—H11B	120.1
H71—O7—H72	108 (3)	C11B—C12B—C13	119.2 (19)
C20—N1—C17	109.2 (6)	C11B—C12B—H12B	120.4
C20—N1—Cd1	125.0 (4)	C13—C12B—H12B	120.4
C17—N1—Cd1	125.8 (4)	C15B—C14B—C13	120.3 (18)
C19—N2—C18	116.5 (5)	C15B—C14B—H14B	119.9
C19—N2—Cd1ii	119.1 (4)	C13—C14B—H14B	119.9
C18—N2—Cd1ii	124.4 (4)	C14B—C15B—C10	121 (2)
O2—C1—O1	120.8 (7)	C14B—C15B—H15B	119.5
O2—C1—C2	120.1 (6)	C10—C15B—H15B	119.5
O1—C1—C2	119.1 (6)	O6B—C16—O6A	106 (3)
O2—C1—Cd1	61.7 (4)	O6B—C16—C13	126 (3)
O1—C1—Cd1	59.1 (4)	O6A—C16—C13	127.2 (13)
C2—C1—Cd1	177.9 (5)	O6A—C16—H16A	116.4
C3—C2—C7	119.5 (7)	C13—C16—H16A	116.4
C3—C2—C1	121.2 (6)	O6B—C16—H16B	117.0
C7—C2—C1	119.3 (6)	C13—C16—H16B	117.0
C4—C3—C2	119.9 (7)	H16A—C16—H16B	125.4
C4—C3—H3	120.0	C18—C17—N1	124.4 (7)
C2—C3—H3	120.0	C18—C17—H17	117.8
C5—C4—C3	120.5 (7)	N1—C17—H17	117.8
C5—C4—H4	119.8	N2—C18—C17	122.0 (7)
C3—C4—H4	119.8	N2—C18—H18	119.0
C4—C5—C6	119.7 (7)	C17—C18—H18	119.0
C4—C5—C8	119.7 (9)	N2—C19—C20	122.1 (7)
C6—C5—C8	120.5 (9)	N2—C19—H19	119.0
C7—C6—C5	120.8 (8)	C20—C19—H19	119.0
C7—C6—H6	119.6	N1—C20—C19	125.7 (7)
C5—C6—H6	119.6	N1—C20—H20	117.1
C6—C7—C2	119.5 (7)	C19—C20—H20	117.1
N1—Cd1—O1—C1	−96.7 (4)	Cd1—O5—C9—O4	0.4 (7)
O7—Cd1—O1—C1	−9.0 (6)	Cd1—O5—C9—C10	178.2 (5)
N2i—Cd1—O1—C1	82.0 (4)	N1—Cd1—C9—O4	87.0 (5)
O5—Cd1—O1—C1	169.1 (5)	O7—Cd1—C9—O4	−3.6 (5)
O4—Cd1—O1—C1	173.4 (4)	N2i—Cd1—C9—O4	−89.3 (5)
O2—Cd1—O1—C1	0.2 (4)	O1—Cd1—C9—O4	176.3 (4)
C9—Cd1—O1—C1	171.0 (4)	O5—Cd1—C9—O4	−179.6 (7)
N1—Cd1—O2—C1	84.5 (5)	O2—Cd1—C9—O4	−159.0 (7)
O7—Cd1—O2—C1	173.5 (5)	C1—Cd1—C9—O4	−177.7 (4)
N2i—Cd1—O2—C1	−99.1 (5)	N1—Cd1—C9—O5	−93.4 (4)
O1—Cd1—O2—C1	−0.2 (4)	O7—Cd1—C9—O5	176.0 (4)
O5—Cd1—O2—C1	−16.1 (6)	N2i—Cd1—C9—O5	90.3 (4)
O4—Cd1—O2—C1	−156.6 (9)	O1—Cd1—C9—O5	−4.0 (5)
C9—Cd1—O2—C1	−29.3 (10)	O4—Cd1—C9—O5	179.6 (7)
N1—Cd1—O4—C9	−94.0 (5)	O2—Cd1—C9—O5	20.6 (9)
O7—Cd1—O4—C9	176.6 (5)	C1—Cd1—C9—O5	2.0 (6)
N2i—Cd1—O4—C9	89.4 (5)	O4—C9—C10—C15A	14.6 (15)
O1—Cd1—O4—C9	−5.0 (6)	O5—C9—C10—C15A	−163.3 (13)
O5—Cd1—O4—C9	0.2 (4)	O4—C9—C10—C11B	167.6 (15)
O2—Cd1—O4—C9	146.8 (9)	O5—C9—C10—C11B	−10.3 (16)
C1—Cd1—O4—C9	5.7 (10)	O4—C9—C10—C11A	−167.9 (13)
N1—Cd1—O5—C9	88.2 (4)	O5—C9—C10—C11A	14.2 (15)
O7—Cd1—O5—C9	−5.7 (6)	O4—C9—C10—C15B	−11.1 (16)
N2i—Cd1—O5—C9	−88.6 (4)	O5—C9—C10—C15B	171.0 (13)
O1—Cd1—O5—C9	176.2 (5)	C15A—C10—C11A—C12A	−7 (2)
O4—Cd1—O5—C9	−0.2 (4)	C11B—C10—C11A—C12A	−97 (8)
O2—Cd1—O5—C9	−171.0 (4)	C15B—C10—C11A—C12A	17 (3)
C1—Cd1—O5—C9	−178.6 (4)	C9—C10—C11A—C12A	175.2 (14)
O7—Cd1—N1—C20	−150.7 (5)	C14B—C13—C12A—C11A	−29 (2)
O1—Cd1—N1—C20	−13.0 (5)	C14A—C13—C12A—C11A	−1 (3)
O5—Cd1—N1—C20	69.8 (5)	C12B—C13—C12A—C11A	79 (5)
O4—Cd1—N1—C20	123.7 (5)	C16—C13—C12A—C11A	178.4 (16)
O2—Cd1—N1—C20	−66.6 (5)	C10—C11A—C12A—C13	7 (3)
C9—Cd1—N1—C20	96.9 (5)	C12A—C13—C14A—C15A	−4 (2)
C1—Cd1—N1—C20	−40.0 (5)	C14B—C13—C14A—C15A	83 (5)
O7—Cd1—N1—C17	29.5 (5)	C12B—C13—C14A—C15A	−30 (2)
O1—Cd1—N1—C17	167.3 (5)	C16—C13—C14A—C15A	176.7 (15)
O5—Cd1—N1—C17	−109.9 (5)	C11B—C10—C15A—C14A	26 (3)
O4—Cd1—N1—C17	−56.0 (5)	C11A—C10—C15A—C14A	2 (2)
O2—Cd1—N1—C17	113.7 (5)	C15B—C10—C15A—C14A	−81 (6)
C9—Cd1—N1—C17	−82.9 (5)	C9—C10—C15A—C14A	179.9 (14)
C1—Cd1—N1—C17	140.2 (5)	C13—C14A—C15A—C10	3 (3)
Cd1—O2—C1—O1	0.4 (7)	C15A—C10—C11B—C12B	−26 (3)
Cd1—O2—C1—C2	−178.8 (5)	C11A—C10—C11B—C12B	75 (7)
Cd1—O1—C1—O2	−0.4 (8)	C15B—C10—C11B—C12B	−1 (3)
Cd1—O1—C1—C2	178.8 (5)	C9—C10—C11B—C12B	180.0 (16)
N1—Cd1—C1—O2	−97.0 (5)	C10—C11B—C12B—C13	−2 (3)
O7—Cd1—C1—O2	−6.9 (5)	C12A—C13—C12B—C11B	−83 (5)
N2i—Cd1—C1—O2	80.2 (5)	C14B—C13—C12B—C11B	2 (3)
O1—Cd1—C1—O2	179.6 (7)	C14A—C13—C12B—C11B	29 (3)
O5—Cd1—C1—O2	168.1 (5)	C16—C13—C12B—C11B	−176.9 (17)
O4—Cd1—C1—O2	163.5 (7)	C12A—C13—C14B—C15B	28 (3)
C9—Cd1—C1—O2	167.2 (4)	C14A—C13—C14B—C15B	−78 (5)
N1—Cd1—C1—O1	83.4 (4)	C12B—C13—C14B—C15B	1 (3)
O7—Cd1—C1—O1	173.5 (4)	C16—C13—C14B—C15B	−180.0 (17)
N2i—Cd1—C1—O1	−99.4 (4)	C13—C14B—C15B—C10	−4 (3)
O5—Cd1—C1—O1	−11.5 (5)	C15A—C10—C15B—C14B	90 (7)
O4—Cd1—C1—O1	−16.1 (10)	C11B—C10—C15B—C14B	5 (3)
O2—Cd1—C1—O1	−179.6 (7)	C11A—C10—C15B—C14B	−18 (3)
C9—Cd1—C1—O1	−12.4 (6)	C9—C10—C15B—C14B	−176.8 (16)
O2—C1—C2—C3	157.1 (7)	C12A—C13—C16—O6B	−8 (5)
O1—C1—C2—C3	−22.1 (10)	C14B—C13—C16—O6B	−159 (5)
O2—C1—C2—C7	−22.7 (10)	C14A—C13—C16—O6B	171 (5)
O1—C1—C2—C7	158.2 (7)	C12B—C13—C16—O6B	21 (5)
C7—C2—C3—C4	2.7 (11)	C12A—C13—C16—O6A	160.9 (19)
C1—C2—C3—C4	−177.0 (7)	C14B—C13—C16—O6A	10 (3)
C2—C3—C4—C5	−1.8 (13)	C14A—C13—C16—O6A	−20 (3)
C3—C4—C5—C6	−0.2 (14)	C12B—C13—C16—O6A	−171 (2)
C3—C4—C5—C8	179.8 (9)	C20—N1—C17—C18	−1.0 (10)
C4—C5—C6—C7	1.2 (15)	Cd1—N1—C17—C18	178.8 (6)
C8—C5—C6—C7	−178.8 (10)	C19—N2—C18—C17	0.5 (11)
C5—C6—C7—C2	−0.3 (14)	Cd1ii—N2—C18—C17	179.5 (6)
C3—C2—C7—C6	−1.7 (12)	N1—C17—C18—N2	0.2 (13)
C1—C2—C7—C6	178.0 (8)	C18—N2—C19—C20	−0.3 (11)
C4—C5—C8—O3	−7.4 (19)	Cd1ii—N2—C19—C20	−179.4 (6)
C6—C5—C8—O3	172.6 (13)	C17—N1—C20—C19	1.2 (10)
Cd1—O4—C9—O5	−0.4 (7)	Cd1—N1—C20—C19	−178.6 (6)
Cd1—O4—C9—C10	−178.2 (6)	N2—C19—C20—N1	−0.6 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H72···O5iii	0.82 (2)	2.10 (6)	2.727 (7)	133 (7)
C18—H18···O6Aiv	0.93	2.52	3.394 (14)	157
C19—H19···O3v	0.93	2.43	3.085 (10)	127
C8—H8···Cg1vi	0.93	2.93	3.691 (10)	147

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the pyrazine ring N1/N2/C17—C20.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H72⋯O5i	0.82 (2)	2.10 (6)	2.727 (7)	133 (7)
C18—H18⋯O6A ii	0.93	2.52	3.394 (14)	157
C19—H19⋯O3iii	0.93	2.43	3.085 (10)	127
C8—H8⋯Cg1iv	0.93	2.93	3.691 (10)	147

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