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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): m1559–m1560.
Published online 2010 November 13. doi:  10.1107/S1600536810046258
PMCID: PMC3011491

Bis[μ-4-(methyl­amino)­benzoato]-κ3 O,O′:O3 O:O,O′-bis­{aqua­[4-(methyl­amino)­benzoato-κ2 O,O′](nicotinamide-κN)cadmium(II)}

Abstract

In the dinuclear centrosymmetric CdII compound, [Cd2(C8H8NO2)4(C6H6N2O)2(H2O)2], the metal atom is chelated by two carboxyl­ate groups from 4-(methyl­amino)­benzoate (PMAB) anions, and coordinated by one nicotinamide and one water mol­ecule; a carboxyl­ate O atom from the adjacent PMAB anion bridges to the Cd atom, completing the irregular seven-coordination geometry. In the crystal, inter­molecular O—H(...)O, N—H(...)O and C—H(...)O hydrogen bonds link the mol­ecules into a three-dimensional network. π–π contacts between the pyridine rings [centroid–centroid distance = 3.965 (1) Å] may further stabilize the structure. A weak C—H(...)π inter­action also occurs.

Related literature

For niacin, see: Krishnamachari (1974 [triangle]). For N,N-diethyl­nicotinamide, see: Bigoli et al. (1972 [triangle]). For related structures, see: Greenaway et al. (1984 [triangle]); Hökelek & Necefoğlu (1996 [triangle]); Hökelek et al. (2009a [triangle],b [triangle],c [triangle],d [triangle], 2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1559-scheme1.jpg

Experimental

Crystal data

  • [Cd2(C8H8NO2)4(C6H6N2O)2(H2O)2]
  • M r = 1105.72
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1559-efi1.jpg
  • a = 9.5286 (2) Å
  • b = 10.1734 (2) Å
  • c = 13.2876 (3) Å
  • α = 72.831 (3)°
  • β = 75.741 (3)°
  • γ = 67.172 (2)°
  • V = 1121.51 (5) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 1.02 mm−1
  • T = 100 K
  • 0.37 × 0.26 × 0.10 mm

Data collection

  • Bruker Kappa APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.734, T max = 0.901
  • 20025 measured reflections
  • 5581 independent reflections
  • 5250 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.024
  • wR(F 2) = 0.061
  • S = 1.08
  • 5581 reflections
  • 324 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 1.77 e Å−3
  • Δρmin = −0.48 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: Mercury (Macrae et al., 2006 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON (Spek, 2009 [triangle]).

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810046258/xu5083sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046258/xu5083Isup2.hkl

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

Acknowledgments

The authors are indebted to Anadolu University and the Medicinal Plants and Medicine Research Centre of Anadolu University, Eskişehir, Turkey, for the use of X-ray diffractometer. This work was supported financially by Kafkas University Research Fund (grant No. 2009-FEF-03).

supplementary crystallographic information

Comment

As a part of our ongoing investigation on transition metal complexes of nicotinamide (NA), one form of niacin (Krishnamachari, 1974), and/or the nicotinic acid derivative N,N-diethylnicotinamide (DENA), an important respiratory stimulant (Bigoli et al., 1972), the title compound was synthesized and its crystal structure is reported herein.

The title compound, (I), consists of dimeric units located around a crystallographic symmetry centre and made up of two Cd cations, four 4-methylaminobenzoate (PMAB) anions, two nicotinamide (NA) ligands and two water molecules (Fig. 1). Each Cd(II) unit is chelated by the carboxylate O atoms of the two PMAB anions, and the two monomeric units are bridged through the two oxygen atoms of the two carboxylate groups about an inversion center. The coordination number of each CdII atom is seven. The Cd1···Cd1i distance is 3.8204 (14) Å and O4-Cd1-O4i angle is 77.12 (5)° (symmetry code: (i) -x, -y, 1 - z).

The average Cd-O bond length (Table 1) is 2.4013 (14) Å, and the Cd atom is displaced out of the least-squares planes of the carboxylate groups (O1/C1/O2) and (O3/C9/O4) by 0.4159 (1) and 0.4085 (1) Å, respectively. In (I), the O1-Cd1-O2 and O3-Cd1-O4 angles are 55.71 (5) and 117.52 (4) °, respectively. The corresponding O-M-O (where M is a metal) angles are 55.96 (4)° and 53.78 (4)° in [Cd2(DMAB)4(NA)2(H2O)2] (Hökelek et al., 2010), 52.91 (4)° and 53.96 (4)° in [Cd(FB)2(INA)2(H2O)].H2O (Hökelek et al., 2009a), 60.70 (4)° in [Co(DMAB)2(INA)(H2O)2] (Hökelek et al., 2009b), 58.45 (9)° in [Mn(DMAB)2(INA)(H2O)2] (Hökelek et al., 2009c), 60.03 (6)° in [Zn(MAB)2(INA)2].H2O (Hökelek et al., 2009d), 58.3 (3)° in [Zn2(DENA)2(HB)4].2H2O (Hökelek & Necefoğlu, 1996) [where NA, INA, DENA, HB, FB, MAB and DMAB are nicotinamide, isonicotinamide, N,N-diethylnicotinamide, 4-hydroxybenzoate, 4-formylbenzoate, 4-methylaminobenzoate and 4-dimethylaminobenzoate, respectively] and 55.2 (1)° in [Cu(Asp)2(py)2] (where Asp is acetylsalicylate and py is pyridine) (Greenaway et al., 1984).

The dihedral angles between the planar carboxylate groups and the adjacent benzene rings A (C2-C7) and B (C10-C15) are 9.86 (16) and 11.74 (11) °, respectively, while those between rings A, B, C (N1/C17-C21), D (Cd1/O1/O2/C1) and E (Cd1/O3/O4/C9) are A/B = 88.35 (6), A/C = 62.90 (7), B/C = 73.43 (6) and D/E = 63.44 (5)°.

In the crystal structure, intermolecular O-H···O, N-H···O and C-H···O hydrogen bonds (Table 2) link the molecules into a three-dimensional network, in which they may be effective in the stabilization of the structure. The π–π contact between the pyridine rings, Cg3—Cg3i [symmetry code: (i) 1 - x, -1 - y, 1 - z, where Cg3 is the centroid of the ring C (N3/C17-C21)] may further stabilize the structure, with centroid-centroid distance of 3.965 (1) Å. There also exists a weak C-H···π interaction (Table 2).

Experimental

The title compound was prepared by the reaction of 3CdSO4.H2O (1.08 g, 5 mmol) in H2O (30 ml) and NA (1.22 g, 10 mmol) in H2O (20 ml) with sodium 4-(methylamino)benzoate (1.73 g, 10 mmol) in H2O (150 ml). The mixture was filtered and set aside to crystallize at ambient temperature for one week, giving colorless single crystals.

Refinement

Atoms H3A, H4A (for NH), H2A, H2B (for NH2) and H61, H62 (for H2O) were located in a difference Fourier map and refined isotropically. The remaining H atoms were positioned geometrically with C—H = 0.93 and 0.96 Å for aromatic and methyl H atoms and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for aromatic H atoms.

Figures

Fig. 1.
The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level. Primed atoms are generated by the symmetry operators: (') - x, - y, 1 - z.

Crystal data

[Cd2(C8H8NO2)4(C6H6N2O)2(H2O)2]Z = 1
Mr = 1105.72F(000) = 560
Triclinic, P1Dx = 1.637 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.5286 (2) ÅCell parameters from 9941 reflections
b = 10.1734 (2) Åθ = 2.4–28.4°
c = 13.2876 (3) ŵ = 1.02 mm1
α = 72.831 (3)°T = 100 K
β = 75.741 (3)°Block, colorless
γ = 67.172 (2)°0.37 × 0.26 × 0.10 mm
V = 1121.51 (5) Å3

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer5581 independent reflections
Radiation source: fine-focus sealed tube5250 reflections with I > 2σ(I)
graphiteRint = 0.023
[var phi] and ω scansθmax = 28.4°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −12→12
Tmin = 0.734, Tmax = 0.901k = −13→13
20025 measured reflectionsl = −17→16

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.024Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.061H atoms treated by a mixture of independent and constrained refinement
S = 1.08w = 1/[σ2(Fo2) + (0.0294P)2 + 0.9733P] where P = (Fo2 + 2Fc2)/3
5581 reflections(Δ/σ)max < 0.001
324 parametersΔρmax = 1.77 e Å3
1 restraintΔρmin = −0.48 e Å3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Cd10.183285 (14)0.043205 (13)0.484176 (10)0.01391 (5)
O10.08486 (15)0.16573 (15)0.62175 (12)0.0210 (3)
O20.32071 (15)0.00805 (14)0.62305 (11)0.0175 (3)
O30.04603 (16)0.29436 (15)0.38267 (12)0.0234 (3)
O4−0.01778 (15)0.10432 (14)0.39110 (11)0.0175 (3)
O50.37181 (18)−0.60649 (17)0.33609 (16)0.0357 (4)
O60.37108 (16)0.12104 (15)0.36256 (12)0.0188 (3)
H610.357 (3)0.205 (4)0.357 (2)0.039 (8)*
H620.462 (4)0.084 (3)0.366 (2)0.042 (8)*
N10.32666 (17)−0.18369 (16)0.44351 (13)0.0157 (3)
N20.1327 (2)−0.4634 (2)0.38591 (18)0.0281 (4)
H2A0.071 (3)−0.385 (3)0.400 (2)0.037 (7)*
H2B0.099 (3)−0.528 (3)0.380 (2)0.039 (8)*
N30.1429 (3)0.0766 (2)1.10668 (16)0.0335 (4)
H3A0.051 (4)0.113 (4)1.137 (3)0.053 (9)*
N4−0.3405 (3)0.5412 (3)−0.00800 (18)0.0413 (5)
H4A−0.345 (5)0.491 (5)−0.048 (3)0.100 (17)*
C10.2004 (2)0.09189 (19)0.66971 (15)0.0155 (3)
C20.1916 (2)0.0959 (2)0.78140 (15)0.0170 (3)
C30.0524 (2)0.1725 (2)0.83657 (17)0.0232 (4)
H3−0.03110.22870.80040.028*
C40.0371 (2)0.1661 (2)0.94354 (18)0.0276 (4)
H4−0.05650.21790.97850.033*
C50.1613 (2)0.0820 (2)1.00047 (16)0.0240 (4)
C60.3012 (2)0.0073 (2)0.94509 (17)0.0251 (4)
H60.3854−0.04780.98080.030*
C70.3151 (2)0.0148 (2)0.83732 (16)0.0227 (4)
H70.4091−0.03540.80170.027*
C80.2541 (4)−0.0243 (3)1.1746 (2)0.0446 (6)
H8A0.2118−0.01991.24740.067*
H8B0.34560.00141.15540.067*
H8C0.2792−0.12181.16610.067*
C9−0.0265 (2)0.23868 (19)0.35120 (15)0.0163 (3)
C10−0.1183 (2)0.32451 (19)0.26270 (15)0.0171 (3)
C11−0.2098 (2)0.2690 (2)0.23138 (16)0.0207 (4)
H11−0.22120.18060.27100.025*
C12−0.2835 (2)0.3414 (2)0.14353 (18)0.0265 (4)
H12−0.34390.30150.12510.032*
C13−0.2687 (2)0.4745 (2)0.08146 (18)0.0288 (5)
C14−0.1827 (3)0.5343 (2)0.1148 (2)0.0324 (5)
H14−0.17490.62460.07690.039*
C15−0.1087 (2)0.4601 (2)0.20394 (18)0.0248 (4)
H15−0.05200.50160.22460.030*
C16−0.3123 (3)0.6668 (3)−0.0834 (2)0.0487 (7)
H16A−0.36100.6892−0.14460.073*
H16B−0.20340.6454−0.10520.073*
H16C−0.35380.7491−0.05060.073*
C170.2634 (2)−0.26755 (19)0.42175 (15)0.0157 (3)
H170.1566−0.24110.43350.019*
C180.3509 (2)−0.39229 (19)0.38237 (15)0.0164 (3)
C190.5101 (2)−0.4288 (2)0.36180 (18)0.0221 (4)
H190.5715−0.50920.33280.027*
C200.5760 (2)−0.3436 (2)0.38513 (19)0.0244 (4)
H200.6823−0.36630.37250.029*
C210.4810 (2)−0.2241 (2)0.42749 (17)0.0193 (4)
H210.5258−0.16940.44560.023*
C220.2834 (2)−0.4945 (2)0.36559 (16)0.0188 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cd10.01123 (7)0.01258 (7)0.01849 (7)−0.00263 (5)−0.00261 (5)−0.00593 (5)
O10.0179 (6)0.0192 (6)0.0262 (7)−0.0015 (5)−0.0074 (5)−0.0088 (6)
O20.0140 (6)0.0195 (6)0.0188 (6)−0.0045 (5)−0.0017 (5)−0.0063 (5)
O30.0197 (7)0.0205 (7)0.0329 (8)−0.0079 (5)−0.0083 (6)−0.0050 (6)
O40.0160 (6)0.0144 (6)0.0197 (7)−0.0047 (5)−0.0032 (5)−0.0003 (5)
O50.0222 (7)0.0254 (8)0.0654 (12)−0.0095 (6)0.0063 (7)−0.0276 (8)
O60.0144 (6)0.0140 (6)0.0246 (7)−0.0028 (5)−0.0022 (5)−0.0031 (5)
N10.0139 (7)0.0135 (7)0.0195 (8)−0.0047 (6)−0.0023 (6)−0.0035 (6)
N20.0165 (8)0.0182 (8)0.0551 (13)−0.0045 (7)−0.0054 (8)−0.0178 (8)
N30.0388 (11)0.0394 (11)0.0193 (9)−0.0110 (9)0.0017 (8)−0.0103 (8)
N40.0413 (12)0.0427 (13)0.0295 (11)−0.0085 (10)−0.0138 (9)0.0059 (10)
C10.0152 (8)0.0129 (7)0.0199 (9)−0.0072 (6)−0.0012 (7)−0.0037 (7)
C20.0170 (8)0.0171 (8)0.0187 (9)−0.0080 (7)−0.0005 (7)−0.0054 (7)
C30.0185 (9)0.0243 (9)0.0265 (10)−0.0051 (7)−0.0019 (8)−0.0092 (8)
C40.0214 (10)0.0338 (11)0.0274 (11)−0.0078 (9)0.0038 (8)−0.0146 (9)
C50.0299 (10)0.0247 (9)0.0199 (10)−0.0138 (8)0.0017 (8)−0.0070 (8)
C60.0236 (10)0.0280 (10)0.0213 (10)−0.0049 (8)−0.0052 (8)−0.0060 (8)
C70.0184 (9)0.0268 (10)0.0211 (10)−0.0043 (8)−0.0016 (7)−0.0085 (8)
C80.0619 (18)0.0446 (15)0.0201 (11)−0.0107 (13)−0.0055 (11)−0.0079 (10)
C90.0109 (8)0.0155 (8)0.0193 (9)−0.0021 (6)0.0002 (6)−0.0045 (7)
C100.0143 (8)0.0138 (8)0.0188 (9)−0.0019 (6)−0.0010 (7)−0.0024 (7)
C110.0209 (9)0.0163 (8)0.0233 (10)−0.0036 (7)−0.0057 (7)−0.0037 (7)
C120.0258 (10)0.0246 (10)0.0279 (11)−0.0039 (8)−0.0096 (8)−0.0061 (8)
C130.0226 (10)0.0263 (10)0.0242 (10)0.0016 (8)−0.0048 (8)0.0011 (8)
C140.0267 (11)0.0198 (10)0.0364 (13)−0.0050 (8)−0.0034 (9)0.0093 (9)
C150.0200 (9)0.0173 (9)0.0328 (11)−0.0068 (7)−0.0034 (8)0.0007 (8)
C160.0348 (14)0.0494 (16)0.0388 (15)−0.0064 (12)−0.0058 (11)0.0129 (12)
C170.0125 (8)0.0144 (8)0.0200 (9)−0.0045 (6)−0.0021 (6)−0.0039 (7)
C180.0157 (8)0.0123 (8)0.0210 (9)−0.0056 (6)−0.0021 (7)−0.0029 (7)
C190.0161 (9)0.0146 (8)0.0334 (11)−0.0036 (7)0.0009 (8)−0.0081 (8)
C200.0118 (8)0.0186 (9)0.0414 (12)−0.0052 (7)0.0001 (8)−0.0079 (8)
C210.0152 (8)0.0142 (8)0.0292 (10)−0.0061 (7)−0.0047 (7)−0.0035 (7)
C220.0185 (9)0.0140 (8)0.0245 (10)−0.0058 (7)−0.0035 (7)−0.0046 (7)

Geometric parameters (Å, °)

Cd1—N12.3265 (15)C6—H60.9300
Cd1—O12.3170 (14)C7—C61.387 (3)
Cd1—O22.3844 (13)C7—H70.9300
Cd1—O32.5099 (15)C8—H8A0.9600
Cd1—O42.3185 (14)C8—H8B0.9600
Cd1—O4i2.5625 (13)C8—H8C0.9600
Cd1—O62.3152 (14)C9—C101.489 (3)
Cd1—C12.7077 (18)C10—C111.397 (3)
O1—C11.267 (2)C10—C151.395 (3)
O2—C11.276 (2)C11—C121.376 (3)
O3—C91.249 (2)C11—H110.9300
O4—C91.289 (2)C12—C131.402 (3)
O5—C221.232 (2)C12—H120.9300
O6—H610.80 (3)C13—N41.381 (3)
O6—H620.81 (3)C13—C141.401 (4)
N1—C171.344 (2)C14—H140.9300
N1—C211.343 (2)C15—C141.393 (3)
N2—C221.319 (3)C15—H150.9300
N2—H2A0.83 (3)C16—N41.444 (3)
N2—H2B0.86 (3)C16—H16A0.9600
N3—C51.366 (3)C16—H16B0.9600
N3—C81.439 (4)C16—H16C0.9600
N3—H3A0.86 (3)C17—C181.391 (2)
N4—H4A0.86 (4)C17—H170.9300
C2—C11.478 (3)C19—C181.390 (3)
C2—C31.400 (3)C19—C201.385 (3)
C2—C71.390 (3)C19—H190.9300
C3—H30.9300C20—H200.9300
C4—C31.377 (3)C21—C201.383 (3)
C4—H40.9300C21—H210.9300
C5—C41.407 (3)C22—C181.507 (2)
C5—C61.399 (3)
O1—Cd1—O255.71 (5)C3—C4—H4119.6
O1—Cd1—O380.21 (5)C5—C4—H4119.6
O1—Cd1—O4106.64 (5)N3—C5—C4119.6 (2)
O1—Cd1—O4i79.05 (5)N3—C5—C6122.2 (2)
O1—Cd1—N1143.81 (5)C6—C5—C4118.18 (19)
O1—Cd1—C127.83 (5)C5—C6—H6119.8
O2—Cd1—O3121.55 (5)C7—C6—C5120.5 (2)
O2—Cd1—O4i91.77 (4)C7—C6—H6119.8
O2—Cd1—C128.12 (5)C2—C7—H7119.3
O3—Cd1—O4i117.52 (4)C6—C7—C2121.35 (18)
O3—Cd1—C1103.17 (5)C6—C7—H7119.3
O4—Cd1—O2161.16 (5)N3—C8—H8A109.5
O4—Cd1—O354.22 (4)N3—C8—H8B109.5
O4—Cd1—O4i77.12 (5)N3—C8—H8C109.5
O4—Cd1—N198.06 (5)H8A—C8—H8B109.5
O4—Cd1—C1133.53 (5)H8A—C8—H8C109.5
O4i—Cd1—C182.17 (5)H8B—C8—H8C109.5
O6—Cd1—O1112.54 (5)O3—C9—O4120.79 (17)
O6—Cd1—O288.69 (5)O3—C9—C10120.31 (17)
O6—Cd1—O373.74 (5)O4—C9—C10118.82 (16)
O6—Cd1—O4105.81 (5)C11—C10—C9121.45 (17)
O6—Cd1—O4i165.88 (5)C15—C10—C9120.91 (18)
O6—Cd1—N184.67 (5)C15—C10—C11117.54 (18)
O6—Cd1—C1104.26 (5)C10—C11—H11119.1
N1—Cd1—O295.16 (5)C12—C11—C10121.82 (19)
N1—Cd1—O3135.97 (5)C12—C11—H11119.1
N1—Cd1—O4i81.23 (5)C11—C12—C13120.8 (2)
N1—Cd1—C1119.34 (6)C11—C12—H12119.6
C1—O1—Cd193.51 (11)C13—C12—H12119.6
C1—O2—Cd190.17 (11)N4—C13—C12119.0 (2)
C9—O3—Cd188.13 (11)N4—C13—C14123.2 (2)
Cd1—O4—Cd1i102.88 (5)C14—C13—C12117.8 (2)
C9—O4—Cd195.93 (11)C13—C14—H14119.6
C9—O4—Cd1i139.46 (11)C15—C14—C13120.8 (2)
Cd1—O6—H61113 (2)C15—C14—H14119.6
Cd1—O6—H62124 (2)C10—C15—H15119.5
H61—O6—H62102 (3)C14—C15—C10121.1 (2)
C17—N1—Cd1123.06 (12)C14—C15—H15119.5
C21—N1—Cd1118.29 (12)N4—C16—H16A109.5
C21—N1—C17118.08 (15)N4—C16—H16B109.5
C22—N2—H2A123 (2)N4—C16—H16C109.5
C22—N2—H2B116.2 (19)H16A—C16—H16B109.5
H2A—N2—H2B120 (3)H16A—C16—H16C109.5
C5—N3—C8123.2 (2)H16B—C16—H16C109.5
C5—N3—H3A117 (2)N1—C17—C18122.70 (16)
C8—N3—H3A117 (2)N1—C17—H17118.6
C13—N4—C16121.7 (2)C18—C17—H17118.6
C13—N4—H4A122 (3)C17—C18—C22123.63 (16)
C16—N4—H4A103 (3)C19—C18—C17118.41 (17)
O1—C1—Cd158.66 (9)C19—C18—C22117.89 (16)
O1—C1—O2119.58 (17)C18—C19—H19120.5
O1—C1—C2119.89 (16)C20—C19—C18119.07 (17)
O2—C1—Cd161.71 (10)C20—C19—H19120.5
O2—C1—C2120.41 (17)C19—C20—H20120.6
C2—C1—Cd1167.59 (12)C21—C20—C19118.87 (17)
C3—C2—C1120.01 (17)C21—C20—H20120.6
C7—C2—C1121.66 (17)N1—C21—C20122.78 (17)
C7—C2—C3118.10 (18)N1—C21—H21118.6
C2—C3—H3119.4C20—C21—H21118.6
C4—C3—C2121.1 (2)O5—C22—N2122.37 (18)
C4—C3—H3119.4O5—C22—C18118.50 (17)
C3—C4—C5120.76 (19)N2—C22—C18119.10 (16)
O2—Cd1—O1—C1−5.82 (10)O6—Cd1—C1—C2−161.5 (6)
O3—Cd1—O1—C1−145.30 (11)N1—Cd1—C1—O1−156.66 (10)
O4—Cd1—O1—C1166.82 (10)N1—Cd1—C1—O233.58 (12)
O4i—Cd1—O1—C193.97 (11)N1—Cd1—C1—C2−69.7 (6)
O6—Cd1—O1—C1−77.59 (11)Cd1—O1—C1—O210.37 (17)
N1—Cd1—O1—C135.80 (15)Cd1—O1—C1—C2−165.67 (14)
O1—Cd1—O2—C15.76 (10)Cd1—O2—C1—O1−10.05 (16)
O3—Cd1—O2—C154.46 (11)Cd1—O2—C1—C2165.96 (14)
O4—Cd1—O2—C1−16.57 (19)Cd1—O3—C9—O49.37 (17)
O4i—Cd1—O2—C1−69.69 (10)Cd1—O3—C9—C10−167.39 (15)
O6—Cd1—O2—C1124.42 (10)Cd1—O4—C9—O3−10.20 (18)
N1—Cd1—O2—C1−151.05 (10)Cd1i—O4—C9—O3107.6 (2)
O1—Cd1—O3—C9−124.35 (11)Cd1—O4—C9—C10166.61 (13)
O2—Cd1—O3—C9−163.39 (10)Cd1i—O4—C9—C10−75.6 (2)
O4—Cd1—O3—C9−5.50 (10)Cd1—N1—C17—C18170.27 (14)
O4i—Cd1—O3—C9−52.25 (12)C21—N1—C17—C18−0.8 (3)
O6—Cd1—O3—C9118.55 (11)Cd1—N1—C21—C20−168.42 (16)
N1—Cd1—O3—C954.71 (13)C17—N1—C21—C203.1 (3)
C1—Cd1—O3—C9−140.19 (11)C8—N3—C5—C4169.5 (2)
O1—Cd1—O4—Cd1i−74.23 (6)C8—N3—C5—C6−11.1 (4)
O1—Cd1—O4—C969.63 (11)C3—C2—C1—Cd1−75.0 (6)
O2—Cd1—O4—Cd1i−55.11 (15)C3—C2—C1—O14.7 (3)
O2—Cd1—O4—C988.75 (17)C3—C2—C1—O2−171.30 (17)
O3—Cd1—O4—Cd1i−138.50 (7)C7—C2—C1—Cd199.4 (6)
O3—Cd1—O4—C95.36 (10)C7—C2—C1—O1179.06 (17)
O4i—Cd1—O4—Cd1i0.0C7—C2—C1—O23.1 (3)
O4i—Cd1—O4—C9143.86 (12)C1—C2—C3—C4173.52 (18)
O6—Cd1—O4—Cd1i165.74 (5)C7—C2—C3—C4−1.0 (3)
O6—Cd1—O4—C9−50.40 (11)C1—C2—C7—C6−173.35 (18)
N1—Cd1—O4—Cd1i79.03 (5)C3—C2—C7—C61.1 (3)
N1—Cd1—O4—C9−137.11 (11)C5—C4—C3—C20.0 (3)
C1—Cd1—O4—Cd1i−65.79 (7)N3—C5—C4—C3−179.5 (2)
C1—Cd1—O4—C978.07 (12)C6—C5—C4—C31.0 (3)
O1—Cd1—N1—C17105.36 (15)N3—C5—C6—C7179.6 (2)
O1—Cd1—N1—C21−83.55 (16)C4—C5—C6—C7−1.0 (3)
O2—Cd1—N1—C17138.80 (14)C2—C7—C6—C5−0.1 (3)
O2—Cd1—N1—C21−50.11 (15)O3—C9—C10—C11−175.08 (17)
O3—Cd1—N1—C17−73.07 (16)O3—C9—C10—C158.7 (3)
O3—Cd1—N1—C2198.02 (15)O4—C9—C10—C118.1 (3)
O4—Cd1—N1—C17−27.75 (15)O4—C9—C10—C15−168.09 (17)
O4i—Cd1—N1—C1747.80 (14)C9—C10—C11—C12−173.83 (18)
O4—Cd1—N1—C21143.34 (14)C15—C10—C11—C122.5 (3)
O4i—Cd1—N1—C21−141.11 (15)C9—C10—C15—C14173.80 (19)
O6—Cd1—N1—C17−133.01 (15)C11—C10—C15—C14−2.5 (3)
O6—Cd1—N1—C2138.08 (14)C10—C11—C12—C130.3 (3)
C1—Cd1—N1—C17123.62 (14)C11—C12—C13—N4177.9 (2)
C1—Cd1—N1—C21−65.29 (15)C11—C12—C13—C14−3.0 (3)
O1—Cd1—C1—O2−169.76 (17)C12—C13—N4—C16−171.1 (2)
O1—Cd1—C1—C287.0 (6)C14—C13—N4—C169.9 (4)
O2—Cd1—C1—O1169.76 (17)N4—C13—C14—C15−178.1 (2)
O2—Cd1—C1—C2−103.2 (6)C12—C13—C14—C152.9 (3)
O3—Cd1—C1—O135.18 (11)C10—C15—C14—C13−0.1 (3)
O3—Cd1—C1—O2−134.59 (10)N1—C17—C18—C19−2.0 (3)
O3—Cd1—C1—C2122.2 (6)N1—C17—C18—C22174.98 (18)
O4—Cd1—C1—O1−17.53 (13)C20—C19—C18—C172.6 (3)
O4i—Cd1—C1—O1−81.36 (11)C20—C19—C18—C22−174.56 (19)
O4—Cd1—C1—O2172.70 (9)C18—C19—C20—C21−0.5 (3)
O4i—Cd1—C1—O2108.88 (10)N1—C21—C20—C19−2.5 (3)
O4—Cd1—C1—C269.5 (6)O5—C22—C18—C17−175.9 (2)
O4i—Cd1—C1—C25.6 (6)O5—C22—C18—C191.1 (3)
O6—Cd1—C1—O1111.46 (11)N2—C22—C18—C172.1 (3)
O6—Cd1—C1—O2−58.31 (11)N2—C22—C18—C19179.1 (2)

Symmetry codes: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2A···O1i0.83 (3)2.13 (3)2.921 (2)160 (2)
N2—H2B···O3ii0.86 (3)2.05 (3)2.901 (3)170 (3)
O6—H61···O5iii0.79 (4)1.91 (4)2.692 (2)167 (3)
O6—H62···O2iv0.81 (4)1.94 (4)2.743 (2)179 (3)
C11—H11···O2i0.932.393.299 (2)165
C17—H17···O1i0.932.363.216 (3)153
C21—H21···O2iv0.932.453.252 (3)145
C19—H19···Cg3v0.932.743.537 (2)144

Symmetry codes: (i) −x, −y, −z+1; (ii) x, y−1, z; (iii) x, y+1, z; (iv) −x+1, −y, −z+1; (v) x+1, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5083).

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