A novel two-dimensional (4,4) network based on dinuclear cadmium secondary building units: poly[([mu]₅-ben­zene-1,4-diacetato)[[mu]₂-1,4-bis­(1,2,4-triazol-1-yl)butane]cadmium(II)]

In the title mixed-ligand metal-organic polymeric compound, [Cd(C₁₀H₈O₄)(C₈H₁₂N₆)]_n or [Cd(PBEA)(BTB)]_n [H₂PBEA is benzene-1,4-diacetic acid and BTB is 1,4-bis­(1,2,4-triazol-1-yl)butane], the asymmetric unit contains one Cd^II ion, one BTB mol­ecule and one PBEA^2- anion. The Cd^II ion is in a slightly distorted penta­gonal-bipyramidal geometry, coordinated by five carboxyl­ate O atoms from three distinct PBEA^2- anions and by two BTB N atoms. There are two coordination patterns for the carboxyl­ate groups of the PBEA^2- ligand, one being a [mu]₁-[eta]¹:[eta]¹ chelating mode and the other a [mu]₂-[eta]²:[eta]¹ bridging mode, while the BTB mol­ecule shows a trans-trans-trans conformation. The crystal structure is constructed from the secondary building unit (SBU) [Cd₂(CO₂)₄N₂O₂], in which the two metal centres are held together by two PBEA^2- linkers. The SBU is connected by BTB and PBEA^2- bridges to form a two-dimensional grid-like (4,4) layer with meshes of dimensions 14.69 × 11.28 Å.

S1. Comment

Considerable attention has been paid to the construction of highly connected metal–organic frameworks (MOFs) with enhanced stability and stable porosity, not only because of their fascinating structures and topologies but also owing to their potential applications in many fields (Kitagawa et al., 2004; Ferey et al., 2005; Roy et al., 2009; Zhang et al., 2009; Jiang et al., 2010). A feasible pathway toward highly connected MOFs is to use the polynuclear metal cluster as a secondary building unit (SBU), because this cluster can effectively reduce the steric hindrance between organic ligands. The mainstream method of constructing such clusters is to utilize carboxylate-containing ligands, since carboxylate groups have excellent coordination capability and flexible coordination patterns. Furthermore, carboxylate groups can prompt core aggregation via bridging metal ions (Eddaoudi et al., 2001).

Compared with the corresponding rigid terephthalic acid, benzene-1,4-diacetic acid (H₂PBEA) may show a variety of coordination modes and conformations owing to the increased flexibility of its two carboxylate groups (Pan et al., 2003; Chen et al., 2006; Braverman & LaDuca, 2007; Wang, Yang et al., 2008 or Wang, Zhang et al., 2008). Meanwhile, 1,4-bis(1,2,4-triazol-1-yl)butane (BTB) can adopt different conformations on the basis of the relative orientation of its CH₂ groups (Li et al., 2006; Gu et al., 2008; Wang, Yang et al., 2008 or Wang, Zhang et al., 2008; Zhu et al., 2009). However, to the best of our knowledge, coordination polymers constructed from H₂PBEA and BTB ligands have not been documented so far. Here, we have selected H₂PBEA and BTB as organic linkers, generating the title new Cd^II coordination polymer, [Cd(BTB)(PBEA)]_n, (I), the crystal structure of which we now report.

Compound (I) crystallizes in the monoclinic space group P21/c, and the asymmetric unit contains one Cd^II ion, one PBEA^2- ligand and one BTB molecule. Each Cd^II centre is seven-coordinated by two triazole N atoms (N1 and N4^v [(iii) in Fig. 1?]) from two different BTB ligands and five O atoms (O1, O2, O3ⁱ, O4ⁱ and O4ⁱⁱ) from three distinct PBEA^2- ligands, resulting in a distorted pentagonal-bipyramid geometry (Fig. 1) [symmetry codes: (i) x - 1, y, z - 1; (ii) -x + 2, -y + 1, -z + 1; (v) [(iii)?] x, y, z - 1]. The equatorial plane is defined by the carboxylate O atoms, while the axial positions are occupied by two BTB N atoms. The Cd—N bond lengths are 2.323 (2) and 2.324 (2) Å, while the Cd—O bond lengths vary greatly from 2.3175 (17) to 2.4986(17 Å. The average Cd—O and Cd—N distances in (I) are comparable with those reported for Cd-based compounds (Liu et al., 2008).

Importantly, each H₂PBEA ligand in (I) is completely deprotonated and links three Cd^II atoms, while there are two coordination patterns for the PBEA^2- ligand, one in a µ₁-η¹:η¹ chelating mode and the other in a µ₂-η²:η¹ briding mode. Two crystallographically equivalent Cd^II atoms are bridged by two tridentate bridging carboxylate groups to form a binuclear motif (the SBU), with a Cd—Cd separation of 3.985 (3) Å, and the SBUs are joined by PBEA^2- ligands to form an infinite ladder-like one-dimensional chain along (110). The separation between the SBUs in the chain is 11.2773 (6) Å. Furthermore, a two-dimensional layer (Fig. 2) perpendicular to the b axis is formed by SBUs double-joined by both BTB and PBEA^2- units. The Miller indices of this plane are (220), in which the BTB molecule shows a trans-trans-trans conformation with a Cd···Cd separation of 14.6837 (8). These sheets are further arranged parallel to the (100) plane and connected by hydrogen bonds, which are formed between alkyl atom C3 and a neighbouring carboxylate atom O3 [C3—H3B···O3^vi; symmetry code: (vi) -1 + x, 1/2 - y, -1/2 + z].

In conclusion, we have synthesized a two-dimensional coordination polymer based on the secondary building unit [Cd₂(CO₂)₄N₂O₂], in which the PBEA^2- ligand forms a one-dimensional chain based on a dinuclear Cd₂ SBU and the BTB ligand is used to extend the framework.

Related literature

For related literature, see: Braverman & LaDuca (2007); Chen et al. (2006); Eddaoudi et al. (2001); Ferey et al. (2005); Gu et al. (2008); Jiang et al. (2010); Kitagawa et al. (2004); Li et al. (2006); Liu et al. (2008); Pan et al. (2003); Roy et al. (2009); Wang, Yang, Liu, Li & Zhang (2008); Wang, Zhang, Yue & Zhang (2008); Zhang et al. (2009); Zhu et al. (2009).

S2. Experimental

A mixture of Cd(NO₃)₂.6H₂O (34.5 mg, 0.1 mmol), H₂PBEA (19.4 mg, 0.1 mmol), BTB (19.2 mg, 0.1 mmol) and NaOH (8.0 mg, 0.2 mmol) in H₂O (10 ml) was sealed in a 16 ml Teflon-lined stainless steel container and heated at 413 K for 72 h. After cooling to room temperature, colourless [White given in CIF - please clarify] block crystals of (I) were collected by filtration and washed several times with water and ethanol (yield 32.5%, based on H₂PBEA). Elemental analysis for C₁₈H₂₀CdN₆O₄ (M_r = 496.81): C 43.52, H 4.06, N 16.92%; found: 43.61, H 4.08, N 16.94%.

S3. Refinement

H atoms were placed in calculated positions and refined using a riding model, with C—H = 0.93 (triazole) or 0.97 Å (methylene), and with U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: SMART (Bruker 2000); cell refinement: SAINT (Bruker 2000); data reduction: SAINT (Bruker 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures

	Fig. 1. A view of the local coordination of the Cd^II cations in (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry codes: (i) x - 1, y, z - 1; (ii) -x + 2, -y + 1, -z + 1; (v) [Should this be (iii)?] x, y, z - 1.] [Please provide a revised plot showing a sharper image and with no atom labels touching atoms or bonds]
	Fig. 2. A view of the two-dimensional framework of (I). [Please provide a sharper plot on a white background to improve clarity]

poly[(µ₅-benzene-1,4-diacetato)[µ₂-1,4-bis(1,2,4-triazol- 1-yl)butane]cadmium(II)]

Crystal data

[Cd(C10H8O4)(C8H12N6)]	F(000) = 1000
Mr = 496.81	Dx = 1.743 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5534 reflections
a = 9.8072 (5) Å	θ = 2.2–28.1°
b = 17.1235 (9) Å	µ = 1.19 mm^−1
c = 14.6837 (6) Å	T = 290 K
β = 129.866 (2)°	Block, white
V = 1892.68 (17) Å^3	0.25 × 0.21 × 0.17 mm
Z = 4

Data collection

Bruker SMART? CCD area-detector diffractometer	3380 independent reflections
Radiation source: fine-focus sealed tube	2930 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
ϕ and ω scans	θmax = 25.1°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→7
Tmin = 0.75, Tmax = 0.816	k = −20→20
9517 measured reflections	l = −8→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.060	H atoms treated by a mixture of independent and constrained refinement
S = 0.90	w = 1/[σ^2(Fo^2) + (0.0387P)^2] where P = (Fo^2 + 2Fc^2)/3
3380 reflections	(Δ/σ)max = 0.004
266 parameters	Δρmax = 0.66 e Å^−3
0 restraints	Δρmin = −0.69 e Å^−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 (Ų)

	x	y	z	Uiso*/Ueq
N4	0.7533 (3)	0.40203 (12)	0.97579 (19)	0.0372 (5)
C7	0.9193 (4)	0.39807 (18)	1.0123 (3)	0.0491 (7)
H7	1.0191	0.3910	1.0914	0.059*
N5	0.9295 (3)	0.40501 (15)	0.9278 (2)	0.0555 (7)
C8	0.6561 (4)	0.41168 (15)	0.8605 (3)	0.0416 (6)
N6	0.7559 (3)	0.41408 (11)	0.82959 (19)	0.0388 (5)
C6	0.7063 (4)	0.43112 (16)	0.7140 (2)	0.0439 (6)
Cd1	0.672989 (19)	0.413547 (9)	0.093614 (13)	0.02599 (8)
O1	0.9121 (2)	0.31542 (10)	0.22481 (15)	0.0437 (4)
O2	0.9654 (2)	0.44107 (10)	0.25622 (15)	0.0395 (4)
O3	1.4234 (2)	0.32343 (10)	0.95406 (15)	0.0416 (4)
O4	1.3812 (2)	0.44795 (10)	0.92418 (15)	0.0475 (5)
N1	0.5945 (3)	0.38750 (13)	0.21005 (18)	0.0372 (5)
N2	0.4250 (3)	0.37661 (13)	0.26298 (19)	0.0422 (5)
N3	0.5930 (3)	0.34905 (11)	0.35077 (17)	0.0332 (4)
C1	0.4337 (4)	0.39860 (15)	0.1806 (2)	0.0378 (6)
H1	0.3374	0.4199	0.1084	0.045*
C2	0.6891 (3)	0.35636 (15)	0.3173 (2)	0.0396 (6)
H2	0.8076	0.3416	0.3629	0.048*
C3	0.6424 (3)	0.31997 (14)	0.4616 (2)	0.0381 (6)
H3A	0.7525	0.2908	0.5042	0.046*
H3B	0.5510	0.2849	0.4445	0.046*
C4	0.6657 (3)	0.38653 (15)	0.5381 (2)	0.0338 (5)
H4A	0.5630	0.4206	0.4903	0.041*
H4B	0.7692	0.4167	0.5647	0.041*
C5	0.6885 (3)	0.35974 (14)	0.6472 (2)	0.0344 (5)
H5A	0.5862	0.3293	0.6223	0.041*
H5B	0.7936	0.3273	0.6979	0.041*
H6A	0.7956	0.4654	0.7263	0.041*
H6B	0.5944	0.4591	0.6664	0.041*
C9	1.0126 (3)	0.37081 (14)	0.2853 (2)	0.0305 (5)
C10	1.1984 (3)	0.35538 (15)	0.4023 (2)	0.0375 (6)
H10A	1.2402	0.3047	0.3998	0.045*
H10B	1.2802	0.3949	0.4153	0.045*
C11	1.1911 (3)	0.35738 (14)	0.5017 (2)	0.0323 (5)
C12	1.1880 (4)	0.28948 (15)	0.5520 (2)	0.0464 (7)
H12	1.1967	0.2414	0.5265	0.056*
C13	1.1724 (4)	0.29185 (15)	0.6388 (2)	0.0455 (7)
H13	1.1726	0.2453	0.6717	0.055*
C14	1.1564 (3)	0.36186 (13)	0.67815 (19)	0.0298 (5)
C15	1.1600 (4)	0.43003 (14)	0.6287 (2)	0.0385 (6)
H15	1.1505	0.4780	0.6539	0.046*
C16	1.1776 (4)	0.42781 (14)	0.5424 (2)	0.0385 (6)
H16	1.1804	0.4744	0.5110	0.046*
C17	1.1427 (3)	0.36511 (14)	0.7745 (2)	0.0328 (5)
H17A	1.0947	0.3164	0.7769	0.039*
H17B	1.0634	0.4070	0.7585	0.039*
C18	1.3254 (3)	0.37895 (15)	0.89228 (19)	0.0283 (5)
H8	0.533 (4)	0.4153 (14)	0.804 (3)	0.052 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N4	0.0407 (12)	0.0471 (13)	0.0331 (12)	0.0077 (9)	0.0280 (11)	0.0051 (9)
C7	0.0410 (16)	0.077 (2)	0.0337 (15)	0.0099 (14)	0.0259 (14)	0.0081 (14)
N5	0.0481 (15)	0.088 (2)	0.0446 (15)	0.0125 (12)	0.0365 (14)	0.0116 (13)
C8	0.0374 (15)	0.0565 (18)	0.0354 (15)	0.0056 (12)	0.0254 (14)	0.0037 (12)
N6	0.0462 (13)	0.0463 (13)	0.0353 (13)	0.0107 (9)	0.0313 (12)	0.0066 (9)
C6	0.0589 (17)	0.0515 (16)	0.0366 (15)	0.0124 (13)	0.0376 (14)	0.0109 (12)
Cd1	0.02463 (11)	0.03296 (12)	0.02093 (11)	0.00226 (6)	0.01485 (9)	0.00190 (6)
O1	0.0374 (9)	0.0393 (10)	0.0387 (10)	−0.0009 (8)	0.0173 (9)	−0.0012 (8)
O2	0.0369 (9)	0.0343 (9)	0.0349 (10)	0.0067 (8)	0.0173 (8)	0.0022 (8)
O3	0.0347 (10)	0.0367 (10)	0.0356 (10)	0.0058 (8)	0.0144 (9)	0.0030 (8)
O4	0.0363 (9)	0.0284 (10)	0.0425 (11)	0.0005 (8)	0.0091 (9)	−0.0027 (8)
N1	0.0377 (12)	0.0489 (12)	0.0311 (11)	−0.0029 (10)	0.0249 (10)	0.0005 (10)
N2	0.0409 (12)	0.0551 (14)	0.0404 (13)	0.0016 (11)	0.0306 (11)	0.0036 (11)
N3	0.0371 (11)	0.0391 (11)	0.0300 (11)	−0.0030 (9)	0.0245 (10)	−0.0019 (9)
C1	0.0382 (14)	0.0465 (15)	0.0313 (14)	0.0000 (11)	0.0234 (13)	−0.0003 (11)
C2	0.0357 (13)	0.0557 (16)	0.0337 (14)	0.0014 (12)	0.0251 (12)	0.0026 (12)
C3	0.0460 (14)	0.0417 (15)	0.0373 (14)	−0.0012 (11)	0.0317 (13)	0.0050 (11)
C4	0.0327 (13)	0.0430 (13)	0.0298 (13)	−0.0030 (11)	0.0220 (12)	0.0019 (11)
C5	0.0327 (12)	0.0460 (15)	0.0310 (13)	0.0013 (11)	0.0235 (11)	0.0056 (11)
C9	0.0295 (12)	0.0428 (15)	0.0244 (12)	0.0075 (11)	0.0197 (11)	0.0061 (11)
C10	0.0291 (12)	0.0455 (15)	0.0333 (14)	0.0099 (11)	0.0179 (12)	0.0047 (11)
C11	0.0232 (11)	0.0396 (14)	0.0239 (12)	0.0056 (10)	0.0104 (10)	0.0025 (10)
C12	0.0653 (18)	0.0315 (14)	0.0421 (15)	0.0099 (12)	0.0344 (15)	0.0003 (12)
C13	0.0655 (18)	0.0294 (13)	0.0410 (15)	0.0016 (12)	0.0338 (15)	0.0039 (11)
C14	0.0228 (11)	0.0324 (13)	0.0232 (12)	−0.0028 (9)	0.0097 (10)	−0.0011 (9)
C15	0.0465 (15)	0.0293 (13)	0.0335 (14)	0.0011 (11)	0.0229 (13)	−0.0032 (10)
C16	0.0478 (15)	0.0295 (13)	0.0346 (14)	−0.0019 (11)	0.0249 (13)	0.0036 (10)
C17	0.0255 (12)	0.0374 (14)	0.0292 (13)	−0.0014 (10)	0.0146 (11)	−0.0009 (10)
C18	0.0283 (12)	0.0324 (13)	0.0263 (12)	−0.0032 (10)	0.0184 (11)	−0.0061 (10)

Geometric parameters (Å, º)

N4—C8	1.316 (3)	N3—C2	1.320 (3)
N4—C7	1.351 (4)	N3—C3	1.456 (3)
N4—Cd1^i	2.324 (2)	C1—H1	0.9300
C7—N5	1.311 (4)	C2—H2	0.9300
C7—H7	0.9300	C3—C4	1.511 (3)
N5—N6	1.362 (3)	C3—H3A	0.9700
C8—N6	1.317 (3)	C3—H3B	0.9700
C8—H8	0.93 (3)	C4—C5	1.539 (3)
N6—C6	1.464 (3)	C4—H4A	0.9700
C6—C5	1.505 (3)	C4—H4B	0.9700
C6—H6A	0.9700	C5—H5A	0.9700
C6—H6B	0.9690	C5—H5B	0.9700
Cd1—O2	2.3171 (17)	C9—C10	1.526 (3)
Cd1—N4^ii	2.324 (2)	C10—C11	1.506 (3)
Cd1—N1	2.3243 (19)	C10—H10A	0.9700
Cd1—O4^iii	2.3662 (17)	C10—H10B	0.9700
Cd1—O4^iv	2.4077 (17)	C11—C16	1.389 (3)
Cd1—O3^iii	2.4780 (17)	C11—C12	1.388 (4)
Cd1—O1	2.4984 (17)	C12—C13	1.380 (4)
O1—C9	1.240 (3)	C12—H12	0.9300
O2—C9	1.261 (3)	C13—C14	1.382 (3)
O3—C18	1.238 (3)	C13—H13	0.9300
O3—Cd1^v	2.4780 (17)	C14—C15	1.387 (3)
O4—C18	1.260 (3)	C14—C17	1.506 (3)
O4—Cd1^v	2.3662 (17)	C15—C16	1.385 (4)
O4—Cd1^iv	2.4077 (17)	C15—H15	0.9300
N1—C2	1.323 (3)	C16—H16	0.9300
N1—C1	1.355 (3)	C17—C18	1.512 (3)
N2—C1	1.320 (3)	C17—H17A	0.9700
N2—N3	1.369 (3)	C17—H17B	0.9700
C8—N4—C7	102.2 (2)	N3—C2—H2	124.5
C8—N4—Cd1^i	129.44 (18)	N1—C2—H2	124.5
C7—N4—Cd1^i	127.35 (18)	N3—C3—C4	110.9 (2)
N5—C7—N4	115.0 (3)	N3—C3—H3A	109.5
N5—C7—H7	122.5	C4—C3—H3A	109.5
N4—C7—H7	122.5	N3—C3—H3B	109.5
C7—N5—N6	102.2 (2)	C4—C3—H3B	109.5
N4—C8—N6	111.2 (2)	H3A—C3—H3B	108.1
N4—C8—H8	128.3 (18)	C3—C4—C5	113.6 (2)
N6—C8—H8	120.5 (18)	C3—C4—H4A	108.8
C8—N6—N5	109.4 (2)	C5—C4—H4A	108.8
C8—N6—C6	129.6 (2)	C3—C4—H4B	108.8
N5—N6—C6	120.8 (2)	C5—C4—H4B	108.8
N6—C6—C5	114.0 (2)	H4A—C4—H4B	107.7
N6—C6—H6A	108.4	C6—C5—C4	108.36 (19)
C5—C6—H6A	109.0	C6—C5—H5A	110.0
N6—C6—H6B	108.5	C4—C5—H5A	110.0
C5—C6—H6B	109.1	C6—C5—H5B	110.0
H6A—C6—H6B	107.7	C4—C5—H5B	110.0
O2—Cd1—N4^ii	89.90 (7)	H5A—C5—H5B	108.4
O2—Cd1—N1	93.20 (7)	O1—C9—O2	122.4 (2)
N4^ii—Cd1—N1	164.07 (8)	O1—C9—C10	120.1 (2)
O2—Cd1—O4^iii	153.73 (7)	O2—C9—C10	117.4 (2)
N4^ii—Cd1—O4^iii	89.83 (7)	C11—C10—C9	108.84 (18)
N1—Cd1—O4^iii	94.22 (7)	C11—C10—H10A	109.9
O2—Cd1—O4^iv	87.29 (6)	C9—C10—H10A	109.9
N4^ii—Cd1—O4^iv	99.17 (7)	C11—C10—H10B	109.9
N1—Cd1—O4^iv	96.59 (7)	C9—C10—H10B	109.9
O4^iii—Cd1—O4^iv	66.84 (7)	H10A—C10—H10B	108.3
O2—Cd1—O3^iii	153.22 (6)	C16—C11—C12	117.3 (2)
N4^ii—Cd1—O3^iii	87.58 (7)	C16—C11—C10	120.8 (2)
N1—Cd1—O3^iii	82.62 (7)	C12—C11—C10	121.8 (2)
O4^iii—Cd1—O3^iii	52.97 (5)	C13—C12—C11	121.4 (2)
O4^iv—Cd1—O3^iii	119.43 (6)	C13—C12—H12	119.3
O2—Cd1—O1	54.00 (6)	C11—C12—H12	119.3
N4^ii—Cd1—O1	85.33 (7)	C12—C13—C14	121.4 (2)
N1—Cd1—O1	83.89 (7)	C12—C13—H13	119.3
O4^iii—Cd1—O1	152.00 (6)	C14—C13—H13	119.3
O4^iv—Cd1—O1	141.16 (6)	C13—C14—C15	117.6 (2)
O3^iii—Cd1—O1	99.21 (6)	C13—C14—C17	121.8 (2)
C9—O1—Cd1	87.72 (14)	C15—C14—C17	120.6 (2)
C9—O2—Cd1	95.64 (14)	C14—C15—C16	121.1 (2)
C18—O3—Cd1^v	91.11 (14)	C14—C15—H15	119.5
C18—O4—Cd1^v	95.84 (14)	C16—C15—H15	119.5
C18—O4—Cd1^iv	150.54 (15)	C11—C16—C15	121.3 (2)
Cd1^v—O4—Cd1^iv	113.16 (7)	C11—C16—H16	119.4
C2—N1—C1	102.8 (2)	C15—C16—H16	119.4
C2—N1—Cd1	129.93 (17)	C14—C17—C18	109.06 (18)
C1—N1—Cd1	127.22 (17)	C14—C17—H17A	109.9
C1—N2—N3	102.5 (2)	C18—C17—H17A	109.9
C2—N3—N2	109.38 (19)	C14—C17—H17B	109.9
C2—N3—C3	130.1 (2)	C18—C17—H17B	109.9
N2—N3—C3	120.53 (18)	H17A—C17—H17B	108.3
N2—C1—N1	114.4 (2)	O3—C18—O4	120.0 (2)
N2—C1—H1	122.8	O3—C18—C17	120.8 (2)
N1—C1—H1	122.8	O4—C18—C17	119.1 (2)
N3—C2—N1	111.0 (2)

Symmetry codes: (i) x, y, z+1; (ii) x, y, z−1; (iii) x−1, y, z−1; (iv) −x+2, −y+1, −z+1; (v) x+1, y, z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···O3^vi	0.97	2.29	3.220 (3)	160

Symmetry code: (vi) x−1, −y+1/2, z−1/2.