Bis{2-[bis­(3,5-dimethyl-1H-pyrazol-1-yl-κN ²)meth­yl]pyridine-κN}cobalt(II) dinitrate

Abstract

The central Co^II ion in the title complex, [Co(C₁₆H₁₉N₅)₂](NO₃)₂, is located on a twofold rotation axis and has a slightly distorted octa­hedral coordination sphere. It is bonded to six N atoms from two 2-[bis­(3,5-dimethyl-1H-pyrazol-1-yl)meth­yl]pyridine ligands. In the crystal, mol­ecules are linked by weak C—H⋯O inter­actions.

Related literature  

For potential applications of similar rigid ligands in electrochemistry, see: Morin et al. (2011 ▶), in catalysis, see: Zhang et al. (2009 ▶), and for their fluxional behaviour, see: Otten et al. (2009 ▶); Arroyo et al. (2000 ▶). For N-heterocyclic rigid scorpion-type ligands, see: Reger et al. (2005 ▶); Liu et al. (2011 ▶).

Experimental  

Crystal data  

• [Co(C₁₆H₁₉N₅)₂](NO₃)₂

• M _r = 745.67

• Monoclinic,

• a = 17.700 (14) Å

• b = 10.965 (9) Å

• c = 18.37 (2) Å

• β = 90.431 (6)°

• V = 3565 (6) ų

• Z = 4

• Mo Kα radiation

• μ = 0.54 mm⁻¹

• T = 296 K

• 0.40 × 0.36 × 0.32 mm

Data collection  

• Bruker APEXII CCD diffractometer

• Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.805, T _max = 0.841

• 8860 measured reflections

• 3297 independent reflections

• 2334 reflections with I > 2σ(I)

• R _int = 0.033

Refinement  

• R[F ² > 2σ(F ²)] = 0.043

• wR(F ²) = 0.131

• S = 1.10

• 3297 reflections

• 235 parameters

• H-atom parameters constrained

• Δρ_max = 0.46 e Å⁻³

• Δρ_min = −0.40 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O3i	0.93	2.45	3.345 (6)	162
C5—H5A⋯O2ii	0.96	2.56	3.405 (7)	147
C10—H10B⋯O3iii	0.96	2.56	3.498 (7)	167
C10—H10C⋯O3ii	0.96	2.29	3.197 (7)	156
C12—H12⋯O1iv	0.93	2.39	3.193 (6)	145
C13—H13⋯O1v	0.93	2.57	3.286 (7)	134
C14—H14⋯O3ii	0.93	2.47	3.322 (6)	152

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

supplementary crystallographic information

Comment

Rigid ligands have captivated attention not only because of their various coordination possibilities and high structural stability, but also because of their potential applications in electrochemistry (Morin et al., 2011), catalysis (Zhang et al., 2009), and fluxional behaviour (Otten et al., 2009; Arroyo et al., 2000). In addition, N-heterocyclic rigid scorpion-type ligands have attracted increased attention due to their nitrogen coordination sites (Reger et al., 2005; Liu et al., 2011). Herein, we report on the synthesis and crystal structure the title complex, [C_O(bpz*mpy)₂](NO₃)₂, synthesized by the reaction of 2-(bis(3,5-dimethyl-1H-pyrazol-1-yl)methyl)pyridine (bpz*mpy), with Co(NO₃).6H₂O.

The molecular structure of the title complex is shown in Fig. 1. The Co atom is situated on a twofold rotation axis and is coordinated by 6 N- atoms from two (bpz*mpy) ligands. The Co—N bond lengths range from 2.131 (2) to 2.149 (3) Å, hence the central cobalt ion has a slightly distorted octahedral coordination sphere.

In the crystal, molecules are linked by weak C—H···O interactions (Table 1 and Fig. 2).

Experimental

To a solution of 2-(bis(3,5-dimethyl-1H-pyrazol-1-yl)methyl)pyridine (0.2 mmol, 56.3 mg) in 10 ml of methanol, Co(NO₃).6H₂O (0.1 mmol, 29.1 mg) was added. The solution was stirred at r.t. for 30 min. Yellow and block-like crystals were obtained by evaporation after one week [Yield: 46 wt%].

Refinement

All the H atoms were included in calculated position and refined in the riding-model approximation: C—H = 0.93, 0.96 and 0.98 Å CH(aromatic), CH₃ and CH(methine), respectively, with U_iso(H)= k ×U_eq(C), where k = 1.5 for CH₃ H atoms and = 1.2 for other H atoms.

Figures

Fig. 1.

The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level [only one of the nitrate anions is shown; H atoms have been omitted for clarity].

Fig. 2.

The crystal packing of the title compound, viewed along the b axis. Weak C-H···O and C-H···N interaction are shown as dashed lines.

Crystal data

[Co(C16H19N5)2](NO3)2	F(000) = 1556
Mr = 745.67	Dx = 1.389 Mg m−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -I 2ya	Cell parameters from 3198 reflections
a = 17.700 (14) Å	θ = 3.1–25.0°
b = 10.965 (9) Å	µ = 0.54 mm−1
c = 18.37 (2) Å	T = 296 K
β = 90.431 (6)°	Block, yellow
V = 3565 (6) Å3	0.40 × 0.36 × 0.32 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer	3297 independent reflections
Radiation source: fine-focus sealed tube	2334 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −21→20
Tmin = 0.805, Tmax = 0.841	k = −13→13
8860 measured reflections	l = −22→14

Refinement

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.048P)2 + 5.1694P] where P = (Fo2 + 2Fc2)/3
3297 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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.

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

	x	y	z	Uiso*/Ueq
Co1	0.25000	0.48144 (5)	0.50000	0.0385 (2)
N1	0.30500 (13)	0.4768 (2)	0.39615 (13)	0.0435 (8)
N2	0.25949 (14)	0.4837 (2)	0.33569 (13)	0.0437 (8)
N3	0.17509 (14)	0.6129 (2)	0.45372 (14)	0.0471 (9)
N4	0.15529 (14)	0.5976 (2)	0.38206 (14)	0.0440 (9)
N5	0.17558 (14)	0.3508 (2)	0.45023 (13)	0.0408 (8)
C1	0.37561 (18)	0.4765 (3)	0.37070 (18)	0.0493 (11)
C2	0.3744 (2)	0.4835 (3)	0.2951 (2)	0.0619 (14)
C3	0.3009 (2)	0.4882 (3)	0.27378 (18)	0.0570 (11)
C4	0.4428 (2)	0.4700 (4)	0.4198 (2)	0.0730 (15)
C5	0.2655 (3)	0.4970 (5)	0.1993 (2)	0.098 (2)
C6	0.14640 (19)	0.7205 (3)	0.4735 (2)	0.0584 (14)
C7	0.1088 (2)	0.7730 (3)	0.4140 (3)	0.0724 (16)
C8	0.11550 (19)	0.6944 (3)	0.3566 (2)	0.0604 (14)
C9	0.1552 (3)	0.7711 (4)	0.5482 (2)	0.0830 (17)
C10	0.0875 (3)	0.7046 (4)	0.2799 (3)	0.096 (2)
C11	0.1499 (2)	0.2504 (3)	0.48366 (18)	0.0521 (11)
C12	0.0989 (2)	0.1722 (3)	0.4522 (2)	0.0626 (14)
C13	0.0733 (2)	0.1950 (3)	0.3826 (2)	0.0647 (14)
C14	0.09957 (19)	0.2970 (3)	0.34717 (18)	0.0532 (11)
C15	0.14991 (16)	0.3725 (3)	0.38241 (15)	0.0378 (9)
C16	0.17815 (17)	0.4864 (3)	0.34485 (16)	0.0411 (9)
O1	0.9501 (3)	0.9744 (3)	0.40558 (19)	0.1213 (19)
O2	0.8920 (2)	0.8352 (4)	0.3465 (2)	0.137 (2)
O3	0.9660 (2)	0.9549 (3)	0.29408 (17)	0.1124 (15)
N6	0.93398 (18)	0.9236 (3)	0.34876 (17)	0.0573 (11)
H2	0.41620	0.48470	0.26470	0.0740*
H4A	0.42860	0.49340	0.46820	0.1090*
H4B	0.48120	0.52430	0.40250	0.1090*
H4C	0.46200	0.38810	0.42050	0.1090*
H5A	0.23610	0.42510	0.18980	0.1460*
H5B	0.30440	0.50400	0.16340	0.1460*
H5C	0.23340	0.56750	0.19700	0.1460*
H7	0.08390	0.84760	0.41360	0.0870*
H9A	0.16930	0.70690	0.58120	0.1250*
H9B	0.10830	0.80640	0.56340	0.1250*
H9C	0.19380	0.83260	0.54830	0.1250*
H10A	0.12970	0.71300	0.24770	0.1430*
H10B	0.05530	0.77470	0.27540	0.1430*
H10C	0.05950	0.63260	0.26730	0.1430*
H11	0.16760	0.23320	0.53030	0.0630*
H12	0.08180	0.10440	0.47760	0.0750*
H13	0.03900	0.14280	0.36000	0.0770*
H14	0.08350	0.31460	0.30000	0.0640*
H16	0.15530	0.48820	0.29610	0.0490*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
Co1	0.0381 (3)	0.0442 (3)	0.0330 (3)	0.0000	−0.0040 (2)	0.0000
N1	0.0362 (14)	0.0570 (16)	0.0372 (14)	−0.0025 (11)	−0.0030 (11)	0.0051 (12)
N2	0.0422 (14)	0.0556 (16)	0.0332 (14)	−0.0038 (12)	−0.0014 (11)	0.0093 (12)
N3	0.0456 (15)	0.0466 (16)	0.0491 (17)	0.0057 (12)	−0.0076 (12)	−0.0009 (12)
N4	0.0404 (14)	0.0433 (15)	0.0480 (16)	−0.0011 (11)	−0.0096 (12)	0.0079 (12)
N5	0.0487 (15)	0.0442 (15)	0.0296 (13)	−0.0063 (11)	−0.0017 (11)	0.0055 (11)
C1	0.0429 (18)	0.0565 (19)	0.0487 (19)	0.0004 (15)	0.0063 (15)	0.0060 (16)
C2	0.054 (2)	0.080 (3)	0.052 (2)	0.0016 (18)	0.0191 (17)	0.0083 (18)
C3	0.065 (2)	0.068 (2)	0.0382 (18)	−0.0038 (18)	0.0082 (16)	0.0114 (16)
C4	0.0379 (19)	0.102 (3)	0.079 (3)	0.0016 (19)	−0.0014 (18)	0.005 (2)
C5	0.097 (3)	0.159 (5)	0.037 (2)	0.004 (3)	0.005 (2)	0.020 (3)
C6	0.051 (2)	0.047 (2)	0.077 (3)	0.0039 (16)	−0.0050 (18)	−0.0030 (18)
C7	0.054 (2)	0.042 (2)	0.121 (4)	0.0073 (16)	−0.016 (2)	0.010 (2)
C8	0.050 (2)	0.047 (2)	0.084 (3)	−0.0003 (16)	−0.0178 (19)	0.0205 (19)
C9	0.092 (3)	0.063 (3)	0.094 (3)	0.020 (2)	−0.003 (3)	−0.023 (2)
C10	0.108 (4)	0.077 (3)	0.101 (4)	0.005 (3)	−0.052 (3)	0.031 (3)
C11	0.071 (2)	0.0503 (19)	0.0351 (18)	−0.0071 (17)	0.0008 (16)	0.0088 (15)
C12	0.081 (3)	0.052 (2)	0.055 (2)	−0.0218 (19)	0.0063 (19)	0.0017 (17)
C13	0.076 (3)	0.061 (2)	0.057 (2)	−0.0229 (19)	−0.004 (2)	−0.0063 (18)
C14	0.057 (2)	0.060 (2)	0.0425 (19)	−0.0131 (17)	−0.0052 (16)	−0.0012 (16)
C15	0.0388 (16)	0.0419 (16)	0.0326 (16)	−0.0018 (12)	−0.0008 (13)	0.0026 (13)
C16	0.0446 (17)	0.0462 (17)	0.0324 (15)	−0.0060 (13)	−0.0084 (13)	0.0086 (13)
O1	0.212 (5)	0.093 (2)	0.059 (2)	−0.021 (3)	0.018 (2)	−0.0085 (18)
O2	0.152 (4)	0.151 (4)	0.107 (3)	−0.085 (3)	0.006 (3)	0.013 (3)
O3	0.151 (3)	0.129 (3)	0.0576 (19)	−0.058 (3)	0.021 (2)	0.0059 (19)
N6	0.069 (2)	0.0579 (18)	0.0448 (19)	0.0007 (16)	−0.0044 (15)	0.0120 (15)

Geometric parameters (Å, º)

Co1—N1	2.149 (3)	C8—C10	1.494 (7)
Co1—N3	2.131 (3)	C11—C12	1.370 (5)
Co1—N5	2.146 (3)	C12—C13	1.376 (5)
Co1—N1i	2.149 (3)	C13—C14	1.377 (5)
Co1—N3i	2.131 (3)	C14—C15	1.375 (5)
Co1—N5i	2.146 (3)	C15—C16	1.514 (5)
O1—N6	1.215 (5)	C2—H2	0.9300
O2—N6	1.222 (5)	C4—H4A	0.9600
O3—N6	1.207 (5)	C4—H4B	0.9600
N1—N2	1.369 (4)	C4—H4C	0.9600
N1—C1	1.338 (4)	C5—H5C	0.9600
N2—C3	1.359 (4)	C5—H5A	0.9600
N2—C16	1.451 (4)	C5—H5B	0.9600
N3—N4	1.370 (4)	C7—H7	0.9300
N3—C6	1.336 (4)	C9—H9A	0.9600
N4—C16	1.457 (4)	C9—H9B	0.9600
N4—C8	1.355 (4)	C9—H9C	0.9600
N5—C11	1.342 (4)	C10—H10A	0.9600
N5—C15	1.344 (4)	C10—H10B	0.9600
C1—C2	1.391 (5)	C10—H10C	0.9600
C1—C4	1.489 (5)	C11—H11	0.9300
C2—C3	1.357 (5)	C12—H12	0.9300
C3—C5	1.504 (5)	C13—H13	0.9300
C6—C7	1.399 (6)	C14—H14	0.9300
C6—C9	1.487 (5)	C16—H16	0.9800
C7—C8	1.368 (6)
N1—Co1—N3	86.93 (9)	C11—C12—C13	119.3 (3)
N1—Co1—N5	83.49 (9)	C12—C13—C14	118.5 (3)
N1—Co1—N1i	177.29 (9)	C13—C14—C15	119.1 (3)
N1—Co1—N3i	94.91 (9)	C14—C15—C16	119.8 (3)
N1—Co1—N5i	94.69 (9)	N5—C15—C16	117.3 (3)
N3—Co1—N5	84.46 (9)	N5—C15—C14	122.9 (3)
N1i—Co1—N3	94.91 (9)	N2—C16—N4	110.5 (2)
N3—Co1—N3i	94.88 (9)	N2—C16—C15	111.6 (2)
N3—Co1—N5i	178.29 (9)	N4—C16—C15	112.5 (2)
N1i—Co1—N5	94.69 (9)	C1—C2—H2	126.00
N3i—Co1—N5	178.29 (9)	C3—C2—H2	126.00
N5—Co1—N5i	96.25 (9)	C1—C4—H4C	110.00
N1i—Co1—N3i	86.93 (9)	H4A—C4—H4C	109.00
N1i—Co1—N5i	83.49 (9)	H4B—C4—H4C	109.00
N3i—Co1—N5i	84.46 (9)	H4A—C4—H4B	109.00
Co1—N1—N2	116.82 (17)	C1—C4—H4A	110.00
Co1—N1—C1	137.8 (2)	C1—C4—H4B	110.00
N2—N1—C1	105.2 (2)	H5A—C5—H5B	109.00
N1—N2—C3	111.3 (2)	H5A—C5—H5C	109.00
N1—N2—C16	119.0 (2)	H5B—C5—H5C	109.00
C3—N2—C16	129.7 (3)	C3—C5—H5A	110.00
Co1—N3—N4	117.03 (17)	C3—C5—H5B	110.00
Co1—N3—C6	136.5 (2)	C3—C5—H5C	110.00
N4—N3—C6	105.9 (2)	C6—C7—H7	126.00
N3—N4—C8	111.4 (2)	C8—C7—H7	126.00
N3—N4—C16	118.9 (2)	C6—C9—H9A	109.00
C8—N4—C16	129.7 (3)	H9A—C9—H9C	109.00
Co1—N5—C11	124.2 (2)	H9B—C9—H9C	109.00
Co1—N5—C15	118.61 (19)	C6—C9—H9C	109.00
C11—N5—C15	117.1 (3)	H9A—C9—H9B	109.00
O1—N6—O2	122.1 (4)	C6—C9—H9B	110.00
O1—N6—O3	118.4 (4)	C8—C10—H10A	110.00
O2—N6—O3	119.1 (3)	C8—C10—H10B	109.00
C2—C1—C4	127.9 (3)	H10B—C10—H10C	109.00
N1—C1—C4	122.2 (3)	H10A—C10—H10C	109.00
N1—C1—C2	110.0 (3)	C8—C10—H10C	109.00
C1—C2—C3	107.3 (3)	H10A—C10—H10B	110.00
C2—C3—C5	131.1 (4)	N5—C11—H11	118.00
N2—C3—C5	122.7 (3)	C12—C11—H11	119.00
N2—C3—C2	106.2 (3)	C11—C12—H12	120.00
N3—C6—C7	109.3 (3)	C13—C12—H12	120.00
N3—C6—C9	122.9 (3)	C12—C13—H13	121.00
C7—C6—C9	127.8 (3)	C14—C13—H13	121.00
C6—C7—C8	107.4 (3)	C15—C14—H14	120.00
C7—C8—C10	130.5 (3)	C13—C14—H14	120.00
N4—C8—C7	106.0 (3)	N2—C16—H16	107.00
N4—C8—C10	123.5 (3)	N4—C16—H16	107.00
N5—C11—C12	123.0 (3)	C15—C16—H16	107.00
N3—Co1—N1—N2	−38.51 (18)	C6—N3—N4—C8	0.7 (3)
N3—Co1—N1—C1	136.0 (3)	N4—N3—C6—C7	−0.3 (3)
N5—Co1—N1—N2	46.26 (18)	Co1—N3—C6—C9	−9.4 (5)
N5—Co1—N1—C1	−139.3 (3)	C6—N3—N4—C16	−179.3 (3)
N3i—Co1—N1—N2	−133.15 (18)	Co1—N3—N4—C8	−172.3 (2)
N3i—Co1—N1—C1	41.3 (3)	Co1—N3—C6—C7	170.7 (2)
N5i—Co1—N1—N2	142.02 (18)	Co1—N3—N4—C16	7.7 (3)
N5i—Co1—N1—C1	−43.5 (3)	N4—N3—C6—C9	179.7 (3)
N1—Co1—N3—N4	36.26 (19)	C8—N4—C16—C15	−122.9 (3)
N1—Co1—N3—C6	−133.9 (3)	N3—N4—C8—C10	178.8 (3)
N5—Co1—N3—N4	−47.50 (19)	N3—N4—C16—N2	−68.3 (3)
N5—Co1—N3—C6	142.3 (3)	N3—N4—C8—C7	−0.9 (4)
N1i—Co1—N3—N4	−141.75 (19)	C16—N4—C8—C7	179.2 (3)
N1i—Co1—N3—C6	48.1 (3)	N3—N4—C16—C15	57.1 (3)
N3i—Co1—N3—N4	130.92 (19)	C8—N4—C16—N2	111.6 (3)
N3i—Co1—N3—C6	−39.3 (3)	C16—N4—C8—C10	−1.1 (5)
N1—Co1—N5—C11	137.7 (3)	C11—N5—C15—C16	179.4 (3)
N1—Co1—N5—C15	−45.4 (2)	Co1—N5—C15—C16	2.3 (3)
N3—Co1—N5—C11	−134.8 (3)	C15—N5—C11—C12	−0.9 (5)
N3—Co1—N5—C15	42.1 (2)	C11—N5—C15—C14	−0.1 (4)
N1i—Co1—N5—C11	−40.3 (3)	Co1—N5—C15—C14	−177.2 (2)
N1i—Co1—N5—C15	136.6 (2)	Co1—N5—C11—C12	176.0 (3)
N5i—Co1—N5—C11	43.7 (3)	C4—C1—C2—C3	−179.7 (4)
N5i—Co1—N5—C15	−139.5 (2)	N1—C1—C2—C3	0.0 (4)
Co1—N1—N2—C3	175.87 (19)	C1—C2—C3—N2	−0.2 (4)
Co1—N1—N2—C16	−3.6 (3)	C1—C2—C3—C5	179.7 (4)
C1—N1—N2—C3	−0.3 (3)	N3—C6—C7—C8	−0.3 (4)
C1—N1—N2—C16	−179.7 (3)	C9—C6—C7—C8	179.8 (4)
N2—N1—C1—C4	179.9 (3)	C6—C7—C8—C10	−179.0 (4)
Co1—N1—C1—C2	−174.7 (2)	C6—C7—C8—N4	0.7 (4)
N2—N1—C1—C2	0.2 (3)	N5—C11—C12—C13	1.3 (5)
Co1—N1—C1—C4	5.0 (5)	C11—C12—C13—C14	−0.6 (5)
C3—N2—C16—C15	120.1 (3)	C12—C13—C14—C15	−0.3 (5)
N1—N2—C16—C15	−60.6 (3)	C13—C14—C15—C16	−178.8 (3)
N1—N2—C3—C2	0.3 (3)	C13—C14—C15—N5	0.7 (5)
C16—N2—C3—C5	−0.2 (5)	N5—C15—C16—N2	61.6 (3)
N1—N2—C3—C5	−179.6 (3)	C14—C15—C16—N2	−119.0 (3)
C3—N2—C16—N4	−113.9 (3)	C14—C15—C16—N4	116.2 (3)
C16—N2—C3—C2	179.6 (3)	N5—C15—C16—N4	−63.3 (3)
N1—N2—C16—N4	65.4 (3)

Symmetry code: (i) −x+1/2, y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3ii	0.93	2.45	3.345 (6)	162
C5—H5A···O2iii	0.96	2.56	3.405 (7)	147
C10—H10B···O3iv	0.96	2.56	3.498 (7)	167
C10—H10C···O3iii	0.96	2.29	3.197 (7)	156
C12—H12···O1v	0.93	2.39	3.193 (6)	145
C13—H13···O1vi	0.93	2.57	3.286 (7)	134
C14—H14···O3iii	0.93	2.47	3.322 (6)	152

Symmetry codes: (ii) −x+3/2, −y+3/2, −z+1/2; (iii) −x+1, y−1/2, −z+1/2; (iv) x−1, y, z; (v) −x+1, −y+1, −z+1; (vi) x−1, y−1, z.