research communications

Acta Cryst. (2016). E72, 1827–1829 https://doi.org/10.1107/S2056989016018247 1827

Received 8 November 2016

Accepted 14 November 2016

Edited by M. Weil, Vienna University of

Technology, Austria

Keywords: crystal structure; cadmium; transition

metal complexes of benzoic acid and nicotina-

mide derivatives.

CCDC reference: 1517222

Supporting information: this article has

supporting information at journals.iucr.org/e

Crystal structure of trans-diaquabis(4-cyano-
benzoato-jO)bis(N,N-diethylnicotinamide-jN)-
cadmium

Nurcan Akduran,a Mustafa Sertçelik,b Ömer Aydoğdu,c Hacali Necefoğluc,d and

Tuncer Hökeleke*

aSANAEM, Saray Mahallesi, Atom Caddesi, No:27, 06980 Saray-Kazan, Ankara, Turkey, bDepartment of Chemical

Engineering, Kafkas University, 36100 Kars, Turkey, cDepartment of Chemistry, Kafkas University, 36100 Kars, Turkey,
dInternational Scientific Research Centre, Baku State University, 1148 Baku, Azerbaijan, and eDepartment of Physics,

Hacettepe University, 06800 Beytepe, Ankara, Turkey. *Correspondence e-mail: merzifon@hacettepe.edu.tr

The mononuclear title cadmium complex, [Cd(C10H14N2O)2(C8H4NO2)2-

(H2O)2], is centrosymmetric and contains two water molecules, two 4-cyano-

benzoate (CB) ligands and two diethylnicotinamide (DENA) ligands. All the

ligands are coordinated to the CdII atom in a monodentate mode. The four

nearest O atoms around the CdII atom form a slightly distorted square-planar

arrangement, with the distorted octahedral coordination sphere being

completed by the two pyridine N atoms of the DENA ligands at distances of

2.3336 (13) Å. The dihedral angle between the carboxylate group and the

adjacent benzene ring is 8.75 (16)�, while the benzene and pyridine rings are

oriented at a dihedral angle of 57.83 (5)�. The water molecules exhibit both

intramolecular [to the non-coordinating carboxylate O atom, enclosing an S(6)

hydrogen-bonding motif, where O� � �O = 2.670 (2) Å] and intermolecular [to the

amide carbonyl O atom, enclosing an R2
2(16) ring motif, where O� � �O =

2.781 (2) Å] O—H� � �O hydrogen bonds. The latter lead to the formation of

supramolecular chains propagating along [110].

1. Chemical context

Nicotinamide (NA) is one form of niacin. A deficiency of this

vitamin leads to loss of copper from the body, known as

pellagra disease. Pellagra patients show unusually high serum

and urinary copper levels (Krishnamachari, 1974). The nico-

tinic acid derivative N,N0-diethylnicotinamide (DENA) is an

important respiratory stimulant (Bigoli et al., 1972). The

crystal structures of some complexes obtained from the

reactions of transition metal(II) ions with NA or DENA as

ligands, e.g. [Ni(NA)2(C7H4ClO2)2(H2O)2] (Hökelek et al.,

2009a) and [Ni(DENA)2(C7H4ClO2)2(H2O)2] (Hökelek et al.,

2009b), have been determined in our laboratory.

The structure–function–coordination relationships of the

arylcarboxylate ion in CdII complexes of benzoic acid deriv-

atives may change depending on the nature and position of the

substituent groups on the benzene ring, the nature of the

additional ligand molecule or solvent, and the pH and

temperature of synthesis (Shnulin et al., 1981; Nadzhafov et al.,

1981; Antsyshkina et al., 1980; Adiwidjaja et al., 1978). When

pyridine and its derivatives are used instead of water mol-

ecules, the structure is completely different (Catterick et al.,

1974). In this context, we synthesized a CdII-containing

compound with 4-cyanobenzoate (CB) and DENA ligands,

namely trans-diaquabis(4-cyanobenzoato-�O)bis(N,N0-di-

ISSN 2056-9890

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ethylnicotinamide-�N)cadmium, [Cd(CB)2(DENA)2(H2O)2],

and report herein its crystal structure.

2. Structural commentary

The asymmetric unit of the mononuclear title complex

contains one CdII atom located on an inversion centre, one CB

ligand, one DENA ligand as well as one water molecule, all

ligands coordinating to the CdII atom in a monodentate mode

(Fig. 1).

The two carboxylate O atoms (O2 and O2i) [symmetry

code: (i) �x, �y, �z] of the two symmetry-related mono-

dentate CB anions and water O atoms (O4 and O4i) form a

slightly distorted square-planar arrangement around the Cd1

atom, while the slightly distorted octahedral coordination

sphere is completed by the two pyridine N atoms (N1 and N1i)

of two DENA ligands (Fig. 1). The Cd—O bond lengths

involving the water O atoms [2.3192 (14) Å] are ca 0.06 Å

longer than those involving the benzoate oxygen atoms

[2.2588 (12) Å]; the Cd—N bond length is the longest with

2.3336 (13) Å in the CdO4N2 octahedron. The Cd1 atom lies

0.7558 (1) Å below the planar (O1/O2/C1) carboxylate group.

The O—Cd—O and O—Cd—N bond angles range from

87.54 (5) to 92.46 (5)�. In the carboxylate groups, the C—O

bonds of the coordinating O atoms [C1—O1 = 1.244 (2) Å and

C1—O2 = 1.259 (2) Å] are 0.015 (2) Å longer than those of

the non-coordinating ones, indicating delocalized bonding

arrangements rather than localized single and double bonds.

The dihedral angle between the carboxylate group (O1/O2/

C1) and the adjacent benzene (C2–C7) ring is 8.75 (16)�, while

the benzene and pyridine (N1/C9–C13) rings are oriented at a

dihedral angle of 57.83 (5)�.

3. Supramolecular features

Intramolecular O—Hw� � �Oc (w = water, c = non-coordinating

carboxylate O atom) hydrogen bonds (Table 1) link the water

molecules by one of their H atoms to the CB anions, enclosing

S(6) hydrogen-bonding motifs (Fig. 1). The other water H

atom is involved in intermolecular O—Hw� � �ODENA (ODENA =

carbonyl O atom of N,N0-diethylnicotinamide) hydrogen

bonds (Table 1), enclosing R2
2(16) ring motifs, leading to the

formation of infinite chains (Fig. 2) propagating along the

[110] direction (Fig. 3).

1828 Akduran et al. � [Cd(C10H14N2O)2(C8H4NO2)2(H2O)2] Acta Cryst. (2016). E72, 1827–1829

research communications

Figure 1
The molecular structure of the title complex with the atom-numbering
scheme for the asymmetric unit. Unlabelled atoms are generated by
symmetry operation (�x, �y, �z). Displacement ellipsoids are drawn at
the 50% probability level. Intramolecular O—Hw� � �Oc (w = water, c =
non-coordinating carboxylate O atom) hydrogen bonds, enclosing S(6)
hydrogen-bonding motifs, are shown as dashed lines.

Table 1
Hydrogen-bond geometry (Å, �).

D—H� � �A D—H H� � �A D� � �A D—H� � �A

O4—H41� � �O3i 0.78 (3) 2.01 (3) 2.781 (2) 169 (3)
O4—H42� � �O1ii 0.87 (3) 1.84 (3) 2.670 (2) 159 (3)

Symmetry codes: (i) x þ 1; y� 1; z; (ii) �x;�y;�z.

Figure 2
Part of the supramolecular chain of the title compound. Intermolecular
O—Hw � � � ODENA (ODENA = carbonyl O atom of N,N0-diethyl-
nicotinamide) hydrogen bonds, enclosing R2

2(16) ring motifs, are shown
as dashed lines. Non-bonding H atoms have been omitted for clarity.



4. Synthesis and crystallization

The title compound was prepared by the reaction of CdSO4�-

8/3H2O (0.64 g, 2.5 mmol) in H2O (50 ml) and diethyl-

nicotinamide (0.89 g, 5 mmol) in H2O (10 ml) with sodium 4-

cyanobenzoate (0.85 g, 5 mmol) in H2O (100 ml). The mixture

was filtered and set aside to crystallize at ambient temperature

for several days, giving colourless single crystals.

5. Refinement

Experimental details including the crystal data, data collection

and refinement are summarized in Table 2. Atoms H41 and

H42 (for H2O) were located in a difference Fourier map and

were refined freely. The C-bound H atoms were positioned

geometrically with C—H = 0.93, 0.97 and 0.96 Å, for aromatic,

methylene and methyl H atoms, respectively, and constrained

to ride on their parent atoms, with Uiso(H) = k � Ueq(C),

where k = 1.5 for methyl H atoms and k = 1.2 for aromatic and

methylene H-atoms.

Acknowledgements

The authors acknowledge the Scientific and Technological

Research Application and Research Center, Sinop University,

Turkey, for the use of the Bruker D8 QUEST diffractometer.

This work was supported financially by Kafkas University,

Scientific Research Projects Coordinator (project No. 2016-

FM-49).

References

Adiwidjaja, G., Rossmanith, E. & Küppers, H. (1978). Acta Cryst.
B34, 3079–3083.

Antsyshkina, A. S., Chiragov, F. M. & Poray-Koshits, M. A. (1980).
Koord. Khim. 15, 1098–1103.

Bigoli, F., Braibanti, A., Pellinghelli, M. A. & Tiripicchio, A. (1972).
Acta Cryst. B28, 962–966.

Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc.
Madison, Wisconsin, USA.

Catterick (neé Drew), J., Hursthouse, M. B., New, D. B. & Thornton,
P. (1974). J. Chem. Soc. Chem. Commun. pp. 843–844.

Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.
Hökelek, T., Dal, H., Tercan, B., Özbek, F. E. & Necefoğlu, H.

(2009a). Acta Cryst. E65, m466–m467.
Hökelek, T., Dal, H., Tercan, B., Özbek, F. E. & Necefoğlu, H.

(2009b). Acta Cryst. E65, m545–m546.
Krishnamachari, K. A. V. R. (1974). Am. J. Clin. Nutr. 27, 108–111.
Nadzhafov, G. N., Shnulin, A. N. & Mamedov, Kh. S. (1981). Zh.

Strukt. Khim. 22, 124–128.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Shnulin, A. N., Nadzhafov, G. N., Amiraslanov, I. R., Usubaliev, B. T.

& Mamedov, Kh. S. (1981). Koord. Khim. 7, 1409–1416.
Spek, A. L. (2009). Acta Cryst. D65, 148–155.

research communications

Acta Cryst. (2016). E72, 1827–1829 Akduran et al. � [Cd(C10H14N2O)2(C8H4NO2)2(H2O)2] 1829

Table 2
Experimental details.

Crystal data
Chemical formula [Cd(C10H14N2O)2(C8H4NO2)2-

(H2O)2]
Mr 797.16
Crystal system, space group Triclinic, P1
Temperature (K) 296
a, b, c (Å) 7.5125 (2), 8.6671 (3), 15.3079 (5)
�, �, � (�) 86.198 (3), 76.249 (4), 74.730 (3)
V (Å3) 933.97 (5)
Z 1
Radiation type Mo K�
� (mm�1) 0.64
Crystal size (mm) 0.15 � 0.11 � 0.10

Data collection
Diffractometer Bruker APEXII CCD
Absorption correction Multi-scan (SADABS; Bruker,

2012)
Tmin, Tmax 0.595, 0.746
No. of measured, independent and

observed [I > 2�(I)] reflections
46611, 4638, 4538

Rint 0.044
(sin �/	)max (�1) 0.669

Refinement
R[F 2 > 2�(F 2)], wR(F 2), S 0.027, 0.068, 1.09
No. of reflections 4638
No. of parameters 243
H-atom treatment H atoms treated by a mixture of

independent and constrained
refinement

�
max, �
min (e �3) 0.42, �1.02

Computer programs: APEX2 and SAINT (Bruker, 2012), SHELXS97 and SHELXL97
(Sheldrick, 2008), ORTEP-3 for Windows and WinGX (Farrugia, 2012) and PLATON
(Spek, 2009).

Figure 3
Part of the crystal structure. Intra- and intermolecular [O–Hw � � � Oc and
O—Hw � � � ODENA, respectively] hydrogen bonds are shown as dashed
lines (see Table 1). Non-bonding H atoms have been omitted for clarity.

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supporting information

sup-1Acta Cryst. (2016). E72, 1827-1829    

supporting information

Acta Cryst. (2016). E72, 1827-1829    [https://doi.org/10.1107/S2056989016018247]

Crystal structure of trans-diaquabis(4-cyanobenzoato-κO)bis(N,N-diethyl-

nicotinamide-κN)cadmium

Nurcan Akduran, Mustafa Sertçelik, Ömer Aydoğdu, Hacali Necefoğlu and Tuncer Hökelek

Computing details 

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); 

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 (Farrugia, 2012) and PLATON (Spek, 2009).

trans-Diaquabis(4-cyanobenzoato-κO)bis(N,N-diethylnicotinamide-κN)cadmium 

Crystal data 

[Cd(C10H14N2O)2(C8H4NO2)2(H2O)2]
Mr = 797.16
Triclinic, P1
Hall symbol: -P 1
a = 7.5125 (2) Å
b = 8.6671 (3) Å
c = 15.3079 (5) Å
α = 86.198 (3)°
β = 76.249 (4)°
γ = 74.730 (3)°
V = 933.97 (5) Å3

Z = 1
F(000) = 410
Dx = 1.417 Mg m−3

Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 9549 reflections
θ = 3.3–28.4°
µ = 0.64 mm−1

T = 296 K
Block, colourless
0.15 × 0.11 × 0.10 mm

Data collection 

Bruker APEXII CCD 
diffractometer

Radiation source: fine-focus sealed tube
Graphite monochromator
φ and ω scans
Absorption correction: multi-scan 

(SADABS; Bruker, 2012)
Tmin = 0.595, Tmax = 0.746

46611 measured reflections
4638 independent reflections
4538 reflections with I > 2σ(I)
Rint = 0.044
θmax = 28.4°, θmin = 3.3°
h = −10→10
k = −11→11
l = −20→20

Refinement 

Refinement on F2

Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.027
wR(F2) = 0.068
S = 1.09
4638 reflections
243 parameters
0 restraints

Primary atom site location: structure-invariant 
direct methods

Secondary atom site location: difference Fourier 
map

Hydrogen site location: inferred from 
neighbouring sites

H atoms treated by a mixture of independent 
and constrained refinement



supporting information

sup-2Acta Cryst. (2016). E72, 1827-1829    

w = 1/[σ2(Fo
2) + (0.0332P)2 + 0.4012P] 

where P = (Fo
2 + 2Fc

2)/3
(Δ/σ)max = 0.001
Δρmax = 0.42 e Å−3

Δρmin = −1.02 e Å−3

Extinction correction: SHELXL97 (Sheldrick, 
2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4

Extinction coefficient: 0.063 (3)

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) 

x y z Uiso*/Ueq

Cd1 0.0000 0.0000 0.0000 0.03023 (7)
O1 0.1214 (2) 0.0630 (2) −0.22948 (11) 0.0618 (4)
O2 0.25363 (17) 0.01600 (17) −0.11090 (8) 0.0414 (3)
O3 −0.5079 (2) 0.6289 (2) 0.12687 (10) 0.0600 (4)
O4 0.1904 (2) −0.1246 (2) 0.09660 (10) 0.0536 (4)
H41 0.281 (4) −0.194 (3) 0.0977 (17) 0.054 (7)*
H42 0.106 (4) −0.123 (3) 0.147 (2) 0.064 (8)*
N1 −0.01528 (19) 0.24366 (16) 0.06156 (9) 0.0312 (3)
N2 −0.4728 (2) 0.58766 (18) 0.27019 (10) 0.0400 (3)
N3 1.1521 (3) −0.2028 (3) −0.46792 (15) 0.0799 (7)
C1 0.2592 (2) 0.0188 (2) −0.19381 (12) 0.0349 (3)
C2 0.4546 (2) −0.03711 (19) −0.25493 (11) 0.0324 (3)
C3 0.6144 (2) −0.0663 (2) −0.21992 (12) 0.0388 (4)
H3 0.6008 −0.0560 −0.1584 0.047*
C4 0.7941 (3) −0.1105 (2) −0.27535 (13) 0.0431 (4)
H4 0.9008 −0.1289 −0.2515 0.052*
C5 0.8134 (3) −0.1272 (2) −0.36706 (12) 0.0412 (4)
C6 0.6546 (3) −0.1021 (3) −0.40264 (13) 0.0498 (5)
H6 0.6684 −0.1152 −0.4639 0.060*
C7 0.4760 (3) −0.0575 (3) −0.34684 (13) 0.0449 (4)
H7 0.3694 −0.0409 −0.3706 0.054*
C8 1.0022 (3) −0.1694 (3) −0.42433 (14) 0.0546 (5)
C9 −0.1852 (2) 0.33349 (19) 0.10302 (11) 0.0317 (3)
H9 −0.2919 0.2972 0.1045 0.038*
C10 −0.2092 (2) 0.47761 (19) 0.14372 (11) 0.0322 (3)
C11 −0.0502 (3) 0.5326 (2) 0.13986 (13) 0.0410 (4)
H11 −0.0611 0.6289 0.1666 0.049*
C12 0.1253 (3) 0.4418 (2) 0.09551 (13) 0.0413 (4)
H12 0.2339 0.4768 0.0916 0.050*
C13 0.1368 (2) 0.2986 (2) 0.05715 (11) 0.0347 (3)
H13 0.2549 0.2382 0.0272 0.042*



supporting information

sup-3Acta Cryst. (2016). E72, 1827-1829    

C14 −0.4097 (2) 0.57261 (19) 0.18114 (11) 0.0357 (3)
C15 −0.3659 (3) 0.5045 (3) 0.33602 (13) 0.0504 (5)
H15A −0.2440 0.4405 0.3041 0.060*
H15B −0.4343 0.4325 0.3716 0.060*
C16 −0.3345 (4) 0.6172 (4) 0.39795 (18) 0.0699 (7)
H16A −0.2536 0.5578 0.4353 0.105*
H16B −0.4540 0.6715 0.4351 0.105*
H16C −0.2757 0.6942 0.3630 0.105*
C17 −0.6711 (3) 0.6737 (3) 0.30629 (14) 0.0497 (5)
H17A −0.7148 0.7492 0.2615 0.060*
H17B −0.6784 0.7340 0.3588 0.060*
C18 −0.7992 (4) 0.5630 (5) 0.3320 (3) 0.0889 (9)
H18A −0.9278 0.6245 0.3520 0.133*
H18B −0.7624 0.4932 0.3796 0.133*
H18C −0.7892 0.5003 0.2808 0.133*

Atomic displacement parameters (Å2) 

U11 U22 U33 U12 U13 U23

Cd1 0.02713 (10) 0.02936 (10) 0.03006 (10) −0.00088 (6) −0.00360 (6) −0.00758 (6)
O1 0.0332 (7) 0.0956 (13) 0.0485 (8) −0.0023 (7) −0.0093 (6) −0.0017 (8)
O2 0.0319 (6) 0.0535 (7) 0.0368 (6) −0.0134 (5) 0.0008 (5) −0.0081 (5)
O3 0.0519 (8) 0.0668 (10) 0.0434 (7) 0.0231 (7) −0.0171 (6) −0.0088 (7)
O4 0.0356 (7) 0.0698 (10) 0.0435 (8) 0.0135 (7) −0.0154 (6) −0.0032 (7)
N1 0.0306 (6) 0.0294 (6) 0.0299 (6) −0.0027 (5) −0.0043 (5) −0.0043 (5)
N2 0.0396 (8) 0.0360 (7) 0.0348 (7) 0.0049 (6) −0.0053 (6) −0.0024 (6)
N3 0.0532 (12) 0.0997 (18) 0.0569 (12) 0.0069 (12) 0.0145 (10) 0.0032 (12)
C1 0.0303 (8) 0.0347 (8) 0.0379 (8) −0.0093 (6) −0.0026 (6) −0.0019 (6)
C2 0.0316 (8) 0.0321 (7) 0.0316 (7) −0.0088 (6) −0.0025 (6) −0.0002 (6)
C3 0.0349 (8) 0.0493 (10) 0.0304 (8) −0.0102 (7) −0.0034 (6) −0.0040 (7)
C4 0.0319 (8) 0.0531 (11) 0.0403 (9) −0.0068 (7) −0.0045 (7) −0.0029 (8)
C5 0.0382 (9) 0.0396 (9) 0.0366 (9) −0.0040 (7) 0.0030 (7) −0.0005 (7)
C6 0.0509 (11) 0.0634 (13) 0.0281 (8) −0.0073 (9) −0.0025 (7) −0.0041 (8)
C7 0.0399 (9) 0.0581 (11) 0.0353 (9) −0.0084 (8) −0.0102 (7) −0.0019 (8)
C8 0.0476 (11) 0.0586 (12) 0.0410 (10) 0.0007 (9) 0.0049 (9) 0.0023 (9)
C9 0.0305 (7) 0.0277 (7) 0.0343 (8) −0.0040 (6) −0.0053 (6) −0.0027 (6)
C10 0.0369 (8) 0.0266 (7) 0.0286 (7) 0.0011 (6) −0.0087 (6) −0.0012 (6)
C11 0.0485 (10) 0.0296 (8) 0.0475 (10) −0.0071 (7) −0.0173 (8) −0.0066 (7)
C12 0.0383 (9) 0.0404 (9) 0.0499 (10) −0.0132 (7) −0.0154 (8) 0.0004 (8)
C13 0.0309 (8) 0.0366 (8) 0.0330 (8) −0.0033 (6) −0.0065 (6) −0.0001 (6)
C14 0.0382 (8) 0.0266 (7) 0.0358 (8) 0.0039 (6) −0.0086 (7) −0.0048 (6)
C15 0.0534 (11) 0.0517 (11) 0.0361 (9) 0.0024 (9) −0.0098 (8) 0.0041 (8)
C16 0.0641 (15) 0.0883 (19) 0.0550 (13) −0.0054 (13) −0.0218 (12) −0.0106 (13)
C17 0.0414 (10) 0.0518 (11) 0.0422 (10) 0.0050 (8) −0.0007 (8) −0.0062 (8)
C18 0.0602 (16) 0.111 (3) 0.097 (2) −0.0325 (17) −0.0083 (16) −0.003 (2)



supporting information

sup-4Acta Cryst. (2016). E72, 1827-1829    

Geometric parameters (Å, º) 

Cd1—O2 2.2588 (12) C6—H6 0.9300
Cd1—O2i 2.2588 (12) C7—H7 0.9300
Cd1—O4 2.3192 (14) C8—N3 1.138 (3)
Cd1—O4i 2.3192 (14) C9—C10 1.383 (2)
Cd1—N1 2.3336 (13) C9—H9 0.9300
Cd1—N1i 2.3336 (13) C10—C11 1.386 (3)
O2—C1 1.259 (2) C10—C14 1.508 (2)
O3—C14 1.233 (2) C11—C12 1.384 (3)
O4—H41 0.78 (3) C11—H11 0.9300
O4—H42 0.87 (3) C12—H12 0.9300
N1—C9 1.340 (2) C13—C12 1.382 (3)
N1—C13 1.335 (2) C13—H13 0.9300
N2—C15 1.471 (2) C14—N2 1.336 (2)
N2—C17 1.469 (2) C15—C16 1.503 (3)
C1—O1 1.244 (2) C15—H15A 0.9700
C2—C1 1.516 (2) C15—H15B 0.9700
C2—C3 1.386 (2) C16—H16A 0.9600
C2—C7 1.395 (2) C16—H16B 0.9600
C3—C4 1.384 (2) C16—H16C 0.9600
C3—H3 0.9300 C17—C18 1.503 (4)
C4—H4 0.9300 C17—H17A 0.9700
C5—C4 1.390 (3) C17—H17B 0.9700
C5—C6 1.387 (3) C18—H18A 0.9600
C5—C8 1.446 (3) C18—H18B 0.9600
C6—C7 1.380 (3) C18—H18C 0.9600

O2i—Cd1—O2 180.00 (6) C6—C7—H7 119.9
O2—Cd1—O4 92.15 (5) N3—C8—C5 178.6 (3)
O2i—Cd1—O4 87.85 (5) N1—C9—C10 123.03 (15)
O2—Cd1—O4i 87.85 (5) N1—C9—H9 118.5
O2i—Cd1—O4i 92.15 (5) C10—C9—H9 118.5
O2—Cd1—N1 92.46 (5) C9—C10—C11 118.26 (15)
O2i—Cd1—N1 87.54 (5) C9—C10—C14 117.30 (15)
O2—Cd1—N1i 87.54 (5) C11—C10—C14 124.12 (15)
O2i—Cd1—N1i 92.46 (5) C10—C11—H11 120.5
O4—Cd1—O4i 180.00 (5) C12—C11—C10 118.93 (16)
O4—Cd1—N1 87.91 (6) C12—C11—H11 120.5
O4i—Cd1—N1 92.09 (6) C11—C12—H12 120.5
O4—Cd1—N1i 92.09 (6) C13—C12—C11 119.07 (16)
O4i—Cd1—N1i 87.91 (6) C13—C12—H12 120.5
N1i—Cd1—N1 180.00 (11) N1—C13—C12 122.42 (16)
C1—O2—Cd1 125.35 (11) N1—C13—H13 118.8
Cd1—O4—H41 141.0 (19) C12—C13—H13 118.8
Cd1—O4—H42 101.5 (18) O3—C14—N2 123.71 (16)
H41—O4—H42 110 (3) O3—C14—C10 117.33 (15)
C9—N1—Cd1 118.45 (11) N2—C14—C10 118.94 (14)



supporting information

sup-5Acta Cryst. (2016). E72, 1827-1829    

C13—N1—Cd1 123.28 (11) N2—C15—C16 112.93 (19)
C13—N1—C9 118.27 (14) N2—C15—H15A 109.0
C14—N2—C15 124.30 (15) N2—C15—H15B 109.0
C14—N2—C17 118.61 (15) C16—C15—H15A 109.0
C17—N2—C15 116.50 (16) C16—C15—H15B 109.0
O1—C1—O2 126.45 (16) H15A—C15—H15B 107.8
O1—C1—C2 117.84 (16) C15—C16—H16A 109.5
O2—C1—C2 115.71 (15) C15—C16—H16B 109.5
C3—C2—C1 120.04 (15) C15—C16—H16C 109.5
C3—C2—C7 119.33 (16) H16A—C16—H16B 109.5
C7—C2—C1 120.63 (16) H16A—C16—H16C 109.5
C2—C3—H3 119.6 H16B—C16—H16C 109.5
C4—C3—C2 120.80 (16) N2—C17—C18 112.4 (2)
C4—C3—H3 119.6 N2—C17—H17A 109.1
C3—C4—C5 119.28 (17) N2—C17—H17B 109.1
C3—C4—H4 120.4 C18—C17—H17A 109.1
C5—C4—H4 120.4 C18—C17—H17B 109.1
C4—C5—C8 118.55 (19) H17A—C17—H17B 107.9
C6—C5—C4 120.48 (17) C17—C18—H18A 109.5
C6—C5—C8 120.97 (18) C17—C18—H18B 109.5
C5—C6—H6 120.1 C17—C18—H18C 109.5
C7—C6—C5 119.80 (17) H18A—C18—H18B 109.5
C7—C6—H6 120.1 H18A—C18—H18C 109.5
C2—C7—H7 119.9 H18B—C18—H18C 109.5
C6—C7—C2 120.28 (17)

O2—Cd1—N1—C9 148.84 (12) C7—C2—C1—O2 172.21 (17)
O2i—Cd1—N1—C9 −31.16 (12) C1—C2—C3—C4 −177.11 (17)
O2—Cd1—N1—C13 −30.80 (13) C7—C2—C3—C4 2.0 (3)
O2i—Cd1—N1—C13 149.20 (13) C1—C2—C7—C6 177.33 (19)
O4—Cd1—N1—C9 −119.09 (12) C3—C2—C7—C6 −1.7 (3)
O4i—Cd1—N1—C9 60.91 (12) C2—C3—C4—C5 −0.6 (3)
O4—Cd1—N1—C13 61.26 (13) C6—C5—C4—C3 −0.9 (3)
O4i—Cd1—N1—C13 −118.74 (13) C8—C5—C4—C3 178.4 (2)
O4—Cd1—O2—C1 152.29 (15) C4—C5—C6—C7 1.2 (3)
O4i—Cd1—O2—C1 −27.71 (15) C8—C5—C6—C7 −178.2 (2)
N1—Cd1—O2—C1 −119.71 (14) C5—C6—C7—C2 0.2 (3)
N1i—Cd1—O2—C1 60.29 (14) N1—C9—C10—C11 1.2 (2)
Cd1—O2—C1—O1 24.2 (3) N1—C9—C10—C14 175.06 (15)
Cd1—O2—C1—C2 −156.03 (11) C9—C10—C11—C12 0.1 (3)
Cd1—N1—C9—C10 178.26 (12) C14—C10—C11—C12 −173.25 (17)
C13—N1—C9—C10 −2.1 (2) C9—C10—C14—O3 −67.2 (2)
Cd1—N1—C13—C12 −178.75 (13) C9—C10—C14—N2 111.03 (19)
C9—N1—C13—C12 1.6 (2) C11—C10—C14—O3 106.3 (2)
C14—N2—C15—C16 122.5 (2) C11—C10—C14—N2 −75.5 (2)
C17—N2—C15—C16 −66.5 (3) C10—C11—C12—C13 −0.6 (3)
C14—N2—C17—C18 95.2 (3) N1—C13—C12—C11 −0.3 (3)
C15—N2—C17—C18 −76.3 (3) O3—C14—N2—C17 1.0 (3)



supporting information

sup-6Acta Cryst. (2016). E72, 1827-1829    

C3—C2—C1—O1 171.04 (18) O3—C14—N2—C15 171.9 (2)
C3—C2—C1—O2 −8.7 (2) C10—C14—N2—C17 −177.05 (17)
C7—C2—C1—O1 −8.0 (3) C10—C14—N2—C15 −6.2 (3)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º) 

D—H···A D—H H···A D···A D—H···A

O4—H41···O3ii 0.78 (3) 2.01 (3) 2.781 (2) 169 (3)
O4—H42···O1i 0.87 (3) 1.84 (3) 2.670 (2) 159 (3)

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