[Diphenyldi(pyrazol-1-yl)methane]-dinitratocobalt(II).

In the title compound, [Co(NO(3))(2)(C(19)H(16)N(4))], the diphenyl-dipyrazolylmethane ligand coordinates to Co(II) in a bidentate fashion forming a six-membered ring with an approximate boat configuration. The mean planes of the two pyrazolyl rings are separated by an angle of 39.6 (2)°. The coordination at the Co(II) center is best described as distorted octa-hedral with two NO(3) (-) anions serving as bidentate ligands for charge balance. The dihedral angle between the mean planes of the two nitrate rings is 85.0 (1)° and that between the mean planes of the two phenyl rings is 73.7 (1)°. The crystal structure is stabilized by weak inter-molecular C-H⋯O and intra-molecular C-H⋯N hydrogen-bond inter-actions.

Related literature

For related structures incorporating diphenyl­dipyrazolyl­methane ligands, see: Shiu et al. (1993 ▶); Tsuji et al. (1999 ▶); Reger et al. (2004 ▶); Shaw et al. (2004 ▶, 2005 ▶, 2009 ▶); Baho & Zargarian (2007a ▶,b ▶).

Experimental

Crystal data

[Co(NO3)2(C19H16N4)]

M = 483.31

Monoclinic,

a = 8.5476 (14) Å

b = 14.8058 (17) Å

c = 16.818 (3) Å

β = 103.383 (4)°

V = 2070.6 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.88 mm−1

T = 200 K

0.50 × 0.30 × 0.30 mm

Data collection

Bruker SMART X2S benchtop diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ▶) T min = 0.668, T max = 0.778

13223 measured reflections

3666 independent reflections

3042 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.118

S = 0.96

3666 reflections

289 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.45 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: APEX2 and SAINT (Bruker, 2009 ▶); data reduction: SAINT and XPREP (Bruker, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b ▶); molecular graphics: SHELXTL (Sheldrick, 2008b ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810000565/jj2017sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000565/jj2017Isup2.hkl

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

[Co(NO3)2(C19H16N4)]	F(000) = 988
Mr = 483.31	Dx = 1.550 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5780 reflections
a = 8.5476 (14) Å	θ = 2.5–24.7°
b = 14.8058 (17) Å	µ = 0.88 mm−1
c = 16.818 (3) Å	T = 200 K
β = 103.383 (4)°	Block, red
V = 2070.6 (5) Å3	0.50 × 0.30 × 0.30 mm
Z = 4

Bruker SMART X2S benchtop diffractometer	3666 independent reflections
Radiation source: microfocus sealed tube	3042 reflections with I > 2σ(I)
doubly curved silicon crystal	Rint = 0.035
ω scans	θmax = 25.1°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −10→10
Tmin = 0.668, Tmax = 0.778	k = −13→17
13223 measured reflections	l = −19→19

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 0.96	w = 1/[σ2(Fo2) + (0.0648P)2 + 0.2696P] where P = (Fo2 + 2Fc2)/3
3666 reflections	(Δ/σ)max = 0.001
289 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.45 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 > 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.

	x	y	z	Uiso*/Ueq
Co1	1.03355 (4)	0.17196 (2)	0.34055 (2)	0.02457 (16)
N1	0.7926 (2)	0.22829 (13)	0.18460 (12)	0.0213 (5)
N2	0.9396 (3)	0.24461 (14)	0.23606 (13)	0.0235 (5)
N3	0.6768 (2)	0.14506 (15)	0.28100 (13)	0.0237 (5)
N4	0.8088 (2)	0.13421 (15)	0.34433 (13)	0.0265 (5)
C1	1.0006 (3)	0.31437 (17)	0.20321 (17)	0.0291 (6)
H1	1.0991	0.3413	0.2258	0.035*
C2	0.8968 (4)	0.34157 (18)	0.13031 (18)	0.0318 (6)
H2	0.9123	0.3885	0.0961	0.038*
C3	0.7677 (3)	0.28493 (17)	0.11973 (16)	0.0278 (6)
H3	0.6786	0.2852	0.0758	0.033*
C4	0.7511 (3)	0.1164 (2)	0.40996 (17)	0.0337 (7)
H4	0.8141	0.1070	0.4623	0.040*
C5	0.5849 (4)	0.1140 (2)	0.38961 (18)	0.0393 (7)
H5	0.5170	0.1029	0.4244	0.047*
C6	0.5413 (3)	0.1313 (2)	0.30753 (17)	0.0311 (6)
H6	0.4368	0.1331	0.2757	0.037*
C7	0.6991 (3)	0.14624 (17)	0.19537 (15)	0.0220 (5)
C8	0.5318 (3)	0.15306 (17)	0.13787 (15)	0.0229 (6)
C9	0.4379 (3)	0.22968 (18)	0.14071 (17)	0.0292 (6)
H9	0.4780	0.2764	0.1766	0.035*
C10	0.2851 (3)	0.23643 (19)	0.09023 (16)	0.0316 (6)
H10	0.2225	0.2874	0.0923	0.038*
C11	0.2264 (3)	0.16684 (19)	0.03673 (18)	0.0325 (7)
H11	0.1240	0.1710	0.0027	0.039*
C12	0.3187 (3)	0.0916 (2)	0.03361 (17)	0.0329 (6)
H12	0.2783	0.0450	−0.0023	0.039*
C13	0.4716 (3)	0.08490 (18)	0.08371 (16)	0.0267 (6)
H13	0.5339	0.0341	0.0808	0.032*
C14	0.7942 (3)	0.06191 (17)	0.18337 (15)	0.0212 (5)
C15	0.7524 (3)	−0.02053 (18)	0.21221 (17)	0.0288 (6)
H15	0.6694	−0.0235	0.2394	0.035*
C16	0.8343 (3)	−0.09812 (19)	0.20048 (18)	0.0356 (7)
H16	0.8047	−0.1533	0.2190	0.043*
C17	0.9592 (3)	−0.0945 (2)	0.16159 (16)	0.0314 (7)
H17	1.0155	−0.1466	0.1550	0.038*
C18	1.0000 (3)	−0.01311 (18)	0.13258 (16)	0.0291 (6)
H18	1.0840	−0.0105	0.1061	0.035*
C19	0.9174 (3)	0.06503 (17)	0.14234 (15)	0.0248 (6)
H19	0.9445	0.1195	0.1214	0.030*
N5	1.2003 (3)	0.03089 (17)	0.38553 (19)	0.0432 (7)
O1	1.1748 (2)	0.06871 (14)	0.31497 (13)	0.0377 (5)
O2	1.1390 (3)	0.07016 (16)	0.43733 (14)	0.0486 (6)
O3	1.2805 (3)	−0.03780 (16)	0.4002 (2)	0.0696 (8)
N6	1.1981 (3)	0.29851 (17)	0.42180 (14)	0.0350 (6)
O4	1.0646 (2)	0.26855 (14)	0.43302 (12)	0.0370 (5)
O5	1.2473 (2)	0.26008 (14)	0.36490 (13)	0.0382 (5)
O6	1.2721 (3)	0.35837 (17)	0.46355 (14)	0.0579 (7)

	U11	U22	U33	U12	U13	U23
Co1	0.0188 (2)	0.0290 (3)	0.0254 (2)	−0.00224 (13)	0.00403 (16)	−0.00001 (14)
N1	0.0205 (11)	0.0212 (11)	0.0222 (11)	−0.0004 (8)	0.0047 (9)	−0.0017 (8)
N2	0.0210 (11)	0.0229 (11)	0.0272 (11)	−0.0030 (9)	0.0067 (9)	−0.0025 (9)
N3	0.0207 (11)	0.0298 (11)	0.0210 (11)	−0.0023 (9)	0.0058 (9)	−0.0030 (9)
N4	0.0220 (11)	0.0344 (12)	0.0223 (11)	−0.0030 (10)	0.0032 (9)	−0.0003 (9)
C1	0.0282 (15)	0.0282 (14)	0.0326 (15)	−0.0059 (11)	0.0102 (12)	−0.0035 (11)
C2	0.0368 (16)	0.0267 (14)	0.0337 (16)	−0.0023 (12)	0.0123 (13)	0.0057 (12)
C3	0.0329 (15)	0.0267 (14)	0.0240 (14)	0.0036 (11)	0.0072 (12)	0.0009 (11)
C4	0.0313 (15)	0.0478 (18)	0.0224 (14)	−0.0073 (13)	0.0076 (12)	−0.0004 (12)
C5	0.0329 (16)	0.059 (2)	0.0305 (16)	−0.0096 (15)	0.0170 (13)	−0.0008 (14)
C6	0.0218 (14)	0.0407 (16)	0.0330 (15)	−0.0029 (12)	0.0109 (12)	−0.0035 (13)
C7	0.0207 (13)	0.0245 (13)	0.0209 (13)	−0.0034 (10)	0.0048 (10)	−0.0021 (10)
C8	0.0206 (13)	0.0260 (13)	0.0228 (13)	0.0004 (10)	0.0065 (11)	0.0006 (10)
C9	0.0270 (14)	0.0292 (15)	0.0316 (15)	0.0006 (11)	0.0070 (12)	−0.0032 (11)
C10	0.0240 (14)	0.0357 (15)	0.0358 (16)	0.0083 (12)	0.0081 (12)	0.0009 (12)
C11	0.0221 (14)	0.0448 (18)	0.0289 (15)	−0.0013 (12)	0.0025 (12)	0.0013 (12)
C12	0.0291 (15)	0.0357 (16)	0.0319 (15)	−0.0050 (12)	0.0029 (12)	−0.0092 (12)
C13	0.0264 (14)	0.0253 (13)	0.0280 (14)	0.0016 (11)	0.0054 (11)	−0.0025 (11)
C14	0.0193 (12)	0.0233 (13)	0.0206 (12)	0.0001 (10)	0.0035 (10)	−0.0017 (10)
C15	0.0274 (14)	0.0293 (15)	0.0311 (15)	0.0018 (11)	0.0100 (12)	0.0050 (11)
C16	0.0411 (17)	0.0235 (14)	0.0426 (17)	0.0040 (12)	0.0106 (14)	0.0090 (12)
C17	0.0324 (15)	0.0278 (15)	0.0314 (15)	0.0090 (11)	0.0022 (13)	−0.0019 (11)
C18	0.0241 (13)	0.0350 (15)	0.0291 (14)	0.0019 (11)	0.0082 (12)	−0.0069 (12)
C19	0.0257 (13)	0.0238 (13)	0.0247 (13)	−0.0027 (11)	0.0055 (11)	−0.0012 (10)
N5	0.0272 (13)	0.0356 (14)	0.0631 (19)	−0.0012 (11)	0.0030 (13)	0.0115 (13)
O1	0.0304 (11)	0.0371 (11)	0.0450 (12)	0.0022 (9)	0.0073 (9)	−0.0004 (10)
O2	0.0457 (13)	0.0550 (14)	0.0452 (13)	0.0062 (11)	0.0108 (11)	0.0152 (11)
O3	0.0546 (16)	0.0409 (14)	0.112 (2)	0.0174 (12)	0.0161 (16)	0.0256 (14)
N6	0.0356 (14)	0.0373 (14)	0.0293 (13)	−0.0105 (11)	0.0020 (11)	−0.0006 (11)
O4	0.0335 (11)	0.0477 (12)	0.0304 (11)	−0.0102 (9)	0.0087 (9)	−0.0085 (9)
O5	0.0325 (11)	0.0439 (12)	0.0383 (12)	−0.0100 (9)	0.0081 (9)	−0.0036 (9)
O6	0.0704 (17)	0.0561 (14)	0.0429 (13)	−0.0357 (13)	0.0045 (12)	−0.0139 (11)

Co1—N4	2.015 (2)	C8—C9	1.397 (4)
Co1—O1	2.054 (2)	C9—C10	1.387 (4)
Co1—N2	2.058 (2)	C9—H9	0.9300
Co1—O4	2.0841 (19)	C10—C11	1.383 (4)
Co1—O5	2.205 (2)	C10—H10	0.9300
Co1—O2	2.248 (2)	C11—C12	1.372 (4)
N1—C3	1.353 (3)	C11—H11	0.9300
N1—N2	1.372 (3)	C12—C13	1.385 (4)
N1—C7	1.488 (3)	C12—H12	0.9300
N2—C1	1.333 (3)	C13—H13	0.9300
N3—C6	1.350 (3)	C14—C19	1.387 (3)
N3—N4	1.370 (3)	C14—C15	1.390 (4)
N3—C7	1.496 (3)	C15—C16	1.383 (4)
N4—C4	1.335 (3)	C15—H15	0.9300
C1—C2	1.396 (4)	C16—C17	1.376 (4)
C1—H1	0.9300	C16—H16	0.9300
C2—C3	1.364 (4)	C17—C18	1.375 (4)
C2—H2	0.9300	C17—H17	0.9300
C3—H3	0.9300	C18—C19	1.385 (4)
C4—C5	1.382 (4)	C18—H18	0.9300
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.368 (4)	N5—O3	1.219 (3)
C5—H5	0.9300	N5—O2	1.258 (4)
C6—H6	0.9300	N5—O1	1.284 (3)
C7—C14	1.528 (3)	N6—O6	1.214 (3)
C7—C8	1.533 (3)	N6—O5	1.266 (3)
C8—C13	1.377 (4)	N6—O4	1.278 (3)
N4—Co1—O1	114.25 (9)	N3—C7—C8	107.4 (2)
N4—Co1—N2	89.17 (9)	C14—C7—C8	114.7 (2)
O1—Co1—N2	110.01 (8)	C13—C8—C9	119.2 (2)
N4—Co1—O4	97.15 (8)	C13—C8—C7	121.4 (2)
O1—Co1—O4	133.44 (8)	C9—C8—C7	119.4 (2)
N2—Co1—O4	103.62 (8)	C10—C9—C8	120.3 (2)
N4—Co1—O5	155.92 (9)	C10—C9—H9	119.8
O1—Co1—O5	88.71 (8)	C8—C9—H9	119.8
N2—Co1—O5	89.55 (8)	C11—C10—C9	119.5 (3)
O4—Co1—O5	59.90 (8)	C11—C10—H10	120.2
N4—Co1—O2	90.96 (9)	C9—C10—H10	120.2
O1—Co1—O2	59.74 (9)	C12—C11—C10	120.3 (3)
N2—Co1—O2	168.60 (9)	C12—C11—H11	119.9
O4—Co1—O2	87.67 (9)	C10—C11—H11	119.9
O5—Co1—O2	94.93 (8)	C11—C12—C13	120.3 (3)
C3—N1—N2	110.5 (2)	C11—C12—H12	119.8
C3—N1—C7	128.0 (2)	C13—C12—H12	119.8
N2—N1—C7	120.40 (19)	C8—C13—C12	120.3 (2)
C1—N2—N1	105.3 (2)	C8—C13—H13	119.8
C1—N2—Co1	130.24 (18)	C12—C13—H13	119.8
N1—N2—Co1	124.46 (15)	C19—C14—C15	119.3 (2)
C6—N3—N4	109.9 (2)	C19—C14—C7	121.8 (2)
C6—N3—C7	129.1 (2)	C15—C14—C7	118.9 (2)
N4—N3—C7	119.0 (2)	C16—C15—C14	120.0 (2)
C4—N4—N3	105.7 (2)	C16—C15—H15	120.0
C4—N4—Co1	128.17 (18)	C14—C15—H15	120.0
N3—N4—Co1	124.22 (16)	C17—C16—C15	120.6 (3)
N2—C1—C2	110.9 (2)	C17—C16—H16	119.7
N2—C1—H1	124.5	C15—C16—H16	119.7
C2—C1—H1	124.5	C18—C17—C16	119.4 (2)
C3—C2—C1	105.5 (2)	C18—C17—H17	120.3
C3—C2—H2	127.2	C16—C17—H17	120.3
C1—C2—H2	127.2	C17—C18—C19	120.8 (2)
N1—C3—C2	107.7 (2)	C17—C18—H18	119.6
N1—C3—H3	126.1	C19—C18—H18	119.6
C2—C3—H3	126.1	C18—C19—C14	119.9 (2)
N4—C4—C5	110.8 (2)	C18—C19—H19	120.1
N4—C4—H4	124.6	C14—C19—H19	120.1
C5—C4—H4	124.6	O3—N5—O2	123.3 (3)
C6—C5—C4	105.6 (3)	O3—N5—O1	121.2 (3)
C6—C5—H5	127.2	O2—N5—O1	115.4 (2)
C4—C5—H5	127.2	N5—O1—Co1	96.51 (17)
N3—C6—C5	107.9 (2)	N5—O2—Co1	88.28 (16)
N3—C6—H6	126.0	O6—N6—O5	123.1 (3)
C5—C6—H6	126.0	O6—N6—O4	122.1 (3)
N1—C7—N3	108.57 (19)	O5—N6—O4	114.8 (2)
N1—C7—C14	109.52 (19)	N6—O4—Co1	95.26 (15)
N3—C7—C14	107.9 (2)	N6—O5—Co1	90.03 (15)
N1—C7—C8	108.6 (2)
C3—N1—N2—C1	2.5 (3)	C14—C7—C8—C13	3.7 (4)
C7—N1—N2—C1	171.1 (2)	N1—C7—C8—C9	−53.9 (3)
C3—N1—N2—Co1	−177.56 (16)	N3—C7—C8—C9	63.3 (3)
C7—N1—N2—Co1	−8.9 (3)	C14—C7—C8—C9	−176.7 (2)
N4—Co1—N2—C1	157.3 (2)	C13—C8—C9—C10	0.8 (4)
O1—Co1—N2—C1	−87.1 (2)	C7—C8—C9—C10	−178.8 (2)
O4—Co1—N2—C1	60.2 (2)	C8—C9—C10—C11	−0.3 (4)
O5—Co1—N2—C1	1.4 (2)	C9—C10—C11—C12	0.0 (4)
O2—Co1—N2—C1	−111.9 (4)	C10—C11—C12—C13	−0.3 (4)
N4—Co1—N2—N1	−22.63 (19)	C9—C8—C13—C12	−1.0 (4)
O1—Co1—N2—N1	92.95 (19)	C7—C8—C13—C12	178.6 (2)
O4—Co1—N2—N1	−119.78 (18)	C11—C12—C13—C8	0.8 (4)
O5—Co1—N2—N1	−178.58 (19)	N1—C7—C14—C19	−19.7 (3)
O2—Co1—N2—N1	68.1 (5)	N3—C7—C14—C19	−137.7 (2)
C6—N3—N4—C4	−1.9 (3)	C8—C7—C14—C19	102.6 (3)
C7—N3—N4—C4	−167.1 (2)	N1—C7—C14—C15	162.4 (2)
C6—N3—N4—Co1	−167.12 (19)	N3—C7—C14—C15	44.4 (3)
C7—N3—N4—Co1	27.7 (3)	C8—C7—C14—C15	−75.3 (3)
O1—Co1—N4—C4	99.7 (3)	C19—C14—C15—C16	0.5 (4)
N2—Co1—N4—C4	−148.7 (3)	C7—C14—C15—C16	178.6 (2)
O4—Co1—N4—C4	−45.1 (3)	C14—C15—C16—C17	1.1 (4)
O5—Co1—N4—C4	−61.7 (3)	C15—C16—C17—C18	−1.5 (4)
O2—Co1—N4—C4	42.7 (3)	C16—C17—C18—C19	0.3 (4)
O1—Co1—N4—N3	−98.5 (2)	C17—C18—C19—C14	1.4 (4)
N2—Co1—N4—N3	13.1 (2)	C15—C14—C19—C18	−1.8 (4)
O4—Co1—N4—N3	116.75 (19)	C7—C14—C19—C18	−179.7 (2)
O5—Co1—N4—N3	100.1 (3)	O3—N5—O1—Co1	178.8 (2)
O2—Co1—N4—N3	−155.5 (2)	O2—N5—O1—Co1	−2.1 (3)
N1—N2—C1—C2	−1.5 (3)	N4—Co1—O1—N5	−74.82 (17)
Co1—N2—C1—C2	178.50 (18)	N2—Co1—O1—N5	−173.28 (15)
N2—C1—C2—C3	0.1 (3)	O4—Co1—O1—N5	53.1 (2)
N2—N1—C3—C2	−2.5 (3)	O5—Co1—O1—N5	97.67 (16)
C7—N1—C3—C2	−170.1 (2)	O2—Co1—O1—N5	1.20 (15)
C1—C2—C3—N1	1.4 (3)	O3—N5—O2—Co1	−179.0 (3)
N3—N4—C4—C5	1.1 (3)	O1—N5—O2—Co1	1.9 (2)
Co1—N4—C4—C5	165.6 (2)	N4—Co1—O2—N5	116.54 (17)
N4—C4—C5—C6	0.0 (4)	O1—Co1—O2—N5	−1.22 (15)
N4—N3—C6—C5	1.9 (3)	N2—Co1—O2—N5	26.0 (5)
C7—N3—C6—C5	165.2 (3)	O4—Co1—O2—N5	−146.35 (17)
C4—C5—C6—N3	−1.1 (3)	O5—Co1—O2—N5	−86.83 (17)
C3—N1—C7—N3	−138.1 (2)	O6—N6—O4—Co1	−178.9 (3)
N2—N1—C7—N3	55.4 (3)	O5—N6—O4—Co1	0.1 (2)
C3—N1—C7—C14	104.3 (3)	N4—Co1—O4—N6	−172.34 (16)
N2—N1—C7—C14	−62.2 (3)	O1—Co1—O4—N6	54.13 (19)
C3—N1—C7—C8	−21.6 (3)	N2—Co1—O4—N6	−81.46 (17)
N2—N1—C7—C8	171.9 (2)	O5—Co1—O4—N6	−0.08 (14)
C6—N3—C7—N1	131.7 (3)	O2—Co1—O4—N6	96.98 (16)
N4—N3—C7—N1	−66.4 (3)	O6—N6—O5—Co1	178.9 (3)
C6—N3—C7—C14	−109.7 (3)	O4—N6—O5—Co1	−0.1 (2)
N4—N3—C7—C14	52.3 (3)	N4—Co1—O5—N6	19.2 (3)
C6—N3—C7—C8	14.4 (4)	O1—Co1—O5—N6	−143.82 (16)
N4—N3—C7—C8	176.4 (2)	N2—Co1—O5—N6	106.16 (16)
N1—C7—C8—C13	126.5 (2)	O4—Co1—O5—N6	0.08 (14)
N3—C7—C8—C13	−116.3 (3)	O2—Co1—O5—N6	−84.34 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O5i	0.93	2.54	3.413 (3)	157
C10—H10···O3ii	0.93	2.59	3.399 (4)	146
C3—H3···O4iii	0.93	2.50	3.313 (3)	146
C19—H19···N1	0.93	2.46	2.799 (3)	102

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯O5i	0.93	2.54	3.413 (3)	157
C10—H10⋯O3ii	0.93	2.59	3.399 (4)	146
C3—H3⋯O4iii	0.93	2.50	3.313 (3)	146
C19—H19⋯N1	0.93	2.46	2.799 (3)	102

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