Crystal structure of (E)-2-(2-{5-[(2-acet­oxy­eth­yl)(meth­yl)amino]­thio­phen-2-yl}vin­yl)-3-methyl­benzo­thia­zolium iodide monohydrate

Sun, X.-S.; Wang, M.-M.; Li, D.-D.

doi:10.1107/S1600536814020121

Crystal structure of (E)-2-(2-{5-[(2-acetoxyethyl)(methyl)amino]thiophen-2-yl}vinyl)-3-methylbenzothiazolium iodide monohydrate

In the cation of the title hydrated salt, C₁₉H₂₁N₂O₂S₂⁺·I⁻·H₂O, the benzothiazolium ring system is approximately planar [maximum deviation = 0.0251 (15) Å], and it makes a small dihedral angle of 1.16 (18)° with the plane of the thiophene ring. In the crystal, the cations, anions and crystalline water molecules are linked by classical O—H

O, O—H

I and weak C—H

O hydrogn bonds, forming a three-dimensional supramolecular network. π–π stacking is observed between parallel thiazole rings of adjacent cations [centroid–centroid distance = 3.5945 (16) Å].

Keywords: crystal structure; benzothiazolium iodide salt; hydrogen bonding.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536814020121/xu5820sup1.cif Contains datablocks I, Global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536814020121/xu5820Isup2.hkl Contains datablock I

CCDC reference: 1023218

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.028
wR factor = 0.071
Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......      0.974 Note
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.26 Report
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O1     --  C18     ..        5.5 su
PLAT242_ALERT_2_C Low       Ueq as Compared to Neighbors for .....        C18 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         39 Report

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ..........    0.00100 Degree
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         74 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

Comment top

Interest in organic compounds with non-linear optical (NLO) properties is driven by the prospective of their applications in optical information technologies. The most common design of molecules with large NLO-active comprises strong electron-donors and acceptors connected by a π-conjugated system (Hao et al., 2009; Zhou et al., 2011). Besides, the introduction about the highpolarizability of sulfur atoms in thiophene rings leads to a stabilization of the conjugated chain and to excellent charge transport properties. In the title compound (I) (Fig. 1), the benzothiazolium-CH═CH-thiophene part of the molecule is nearly coplanar (plane of CH═CH makes angles of 0.663 (8)° and 0.847 (1)° with the planes of the benzothiazolium and the thiophene rings), while in related benzothiazolium derivatives (Quist et al. 2009), the corresponding angles are 5.61 (18)° and 1.78 (19)°, respectively.

Related literature top

For background to this study, see: Hao et al. (2009); Zhou et al. (2011). For the crystal structures of related benzothiazolium derivatives, see: Quist et al. (2009).

Experimental top

A mixture of 2,3-dimethylbenzothiazolium iodide (1 mmol), 5-[(2-hydroxyethyl)methylamino]thiophene-2-carbaldehyde (1 mmol) and acetic anhydride (20 ml) was refluxed for 20 min, than poured into a warm solution of potassium iodide (4 mmol) in water (20 ml). The precipitated product was filtered, washed with water and recrystallized from a methanol/water solution. ¹H NMR: (400 Hz, DMSO-d₆), d(p.p.m.):8.14 (d, 1H), 8.11 (d, 1H), 7.89 (d, 1H), 7.83 (s, 1H), 7.66 (t, 1H), 7.53 (t, 1H), 6.73 (s, 1H), 6.54 (d, 1H), 4.33 (t, 2H), 4.00 (s, 3H), 3.85 (t, 2H), 3.24 (s, 3H), 1.94 (s, 3H).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. : The molecular structure of the title compound (I) showing 30% probability displacement ellipsoids.

(E)-2-(2-{5-[(2-Acetoxyethyl)(methyl)amino]thiophen-2-yl}vinyl)-3-methylbenzothiazolium iodide monohydrate top

Crystal data top

C₁₉H₂₁N₂O₂S₂⁺·I⁻·H₂O	Z = 2
M_r = 518.43	F(000) = 520
Triclinic, P1	D_x = 1.566 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6689 (9) Å	Cell parameters from 3223 reflections
b = 11.1237 (11) Å	θ = 2.6–26.8°
c = 11.1693 (11) Å	µ = 1.67 mm⁻¹
α = 94.420 (1)°	T = 293 K
β = 110.067 (1)°	Block, red
γ = 99.919 (1)°	0.20 × 0.20 × 0.18 mm
V = 1099.40 (18) Å³

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3638 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.016
Graphite monochromator	θ_max = 26.0°, θ_min = 1.9°
phi and ω scans	h = −11→11
8450 measured reflections	k = −13→13
4211 independent reflections	l = −13→13

Refinement top

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.071	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.036P)² + 0.5766P] where P = (F_o² + 2F_c²)/3
4211 reflections	(Δ/σ)_max < 0.001
247 parameters	Δρ_max = 0.67 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₉H₂₁N₂O₂S₂⁺·I⁻·H₂O	γ = 99.919 (1)°
M_r = 518.43	V = 1099.40 (18) Å³
Triclinic, P1	Z = 2
a = 9.6689 (9) Å	Mo Kα radiation
b = 11.1237 (11) Å	µ = 1.67 mm⁻¹
c = 11.1693 (11) Å	T = 293 K
α = 94.420 (1)°	0.20 × 0.20 × 0.18 mm
β = 110.067 (1)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3638 reflections with I > 2σ(I)
8450 measured reflections	R_int = 0.016
4211 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.071	H-atom parameters constrained
S = 0.97	Δρ_max = 0.67 e Å⁻³
4211 reflections	Δρ_min = −0.30 e Å⁻³
247 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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.

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

	x	y	z	U_iso*/U_eq
C1	0.8392 (4)	1.1137 (3)	1.1880 (3)	0.0617 (8)
H1	0.9151	1.1225	1.1540	0.074*
C2	0.8380 (4)	1.2036 (3)	1.2804 (4)	0.0735 (10)
H2	0.9138	1.2747	1.3076	0.088*
C3	0.7274 (4)	1.1903 (3)	1.3330 (3)	0.0710 (9)
H3	0.7318	1.2513	1.3968	0.085*
C4	0.6105 (4)	1.0881 (3)	1.2926 (3)	0.0608 (8)
H4	0.5353	1.0797	1.3274	0.073*
C5	0.6088 (3)	0.9985 (2)	1.1986 (3)	0.0476 (6)
C6	0.7227 (3)	1.0101 (3)	1.1481 (3)	0.0483 (6)
C7	0.8124 (4)	0.8983 (3)	0.9953 (3)	0.0698 (9)
H7A	0.7863	0.8181	0.9452	0.105*
H7B	0.9112	0.9100	1.0600	0.105*
H7C	0.8113	0.9604	0.9401	0.105*
C8	0.5782 (3)	0.8216 (2)	1.0354 (2)	0.0432 (6)
C9	0.5304 (3)	0.7106 (3)	0.9491 (3)	0.0481 (6)
H9	0.5890	0.6925	0.9021	0.058*
C10	0.4006 (3)	0.6289 (3)	0.9325 (3)	0.0485 (6)
H10	0.3468	0.6512	0.9824	0.058*
C11	0.3379 (3)	0.5172 (3)	0.8514 (3)	0.0498 (6)
C12	0.2052 (3)	0.4370 (3)	0.8388 (3)	0.0565 (7)
H12	0.1471	0.4533	0.8869	0.068*
C13	0.1650 (3)	0.3322 (3)	0.7507 (3)	0.0553 (7)
H13	0.0780	0.2720	0.7329	0.066*
C14	0.2699 (3)	0.3259 (3)	0.6907 (3)	0.0481 (6)
C15	0.1367 (4)	0.1291 (3)	0.5589 (3)	0.0627 (8)
H15A	0.1256	0.0933	0.6314	0.094*
H15B	0.1532	0.0685	0.5022	0.094*
H15C	0.0469	0.1569	0.5134	0.094*
C16	0.3834 (4)	0.2325 (3)	0.5509 (3)	0.0616 (8)
H16A	0.4097	0.1522	0.5533	0.074*
H16B	0.4725	0.2934	0.6045	0.074*
C17	0.3371 (4)	0.2598 (3)	0.4147 (3)	0.0679 (9)
H17A	0.4175	0.2563	0.3821	0.081*
H17B	0.2482	0.1996	0.3597	0.081*
C18	0.2295 (4)	0.4128 (3)	0.3042 (4)	0.0652 (9)
C19	0.1969 (5)	0.5379 (4)	0.3189 (5)	0.1004 (14)
H19A	0.1788	0.5703	0.2390	0.151*
H19B	0.2815	0.5915	0.3852	0.151*
H19C	0.1093	0.5326	0.3420	0.151*
I1	0.77902 (2)	0.097609 (18)	0.70194 (2)	0.06164 (9)
N1	0.7029 (3)	0.9082 (2)	1.0575 (2)	0.0474 (5)
N2	0.2650 (3)	0.2336 (2)	0.6039 (2)	0.0543 (6)
O1	0.3053 (3)	0.38152 (19)	0.4157 (2)	0.0676 (6)
O2	0.0975 (4)	0.6590 (3)	0.0227 (3)	0.1165 (11)
H2A	0.0901	0.7284	0.0548	0.175*
H2C	0.0115	0.6207	−0.0300	0.175*
O3	0.1931 (4)	0.3467 (3)	0.2039 (3)	0.1068 (10)
S1	0.47604 (8)	0.86129 (6)	1.12820 (7)	0.04896 (17)
S2	0.41617 (9)	0.45592 (7)	0.74660 (7)	0.05390 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0601 (19)	0.0565 (18)	0.0615 (19)	0.0025 (15)	0.0177 (16)	0.0112 (15)
C2	0.076 (2)	0.0509 (19)	0.074 (2)	−0.0031 (17)	0.0110 (19)	0.0046 (16)
C3	0.081 (2)	0.0509 (18)	0.070 (2)	0.0110 (17)	0.0186 (19)	−0.0075 (16)
C4	0.068 (2)	0.0529 (17)	0.0599 (18)	0.0168 (15)	0.0211 (16)	0.0001 (14)
C5	0.0508 (16)	0.0426 (14)	0.0440 (15)	0.0127 (12)	0.0091 (12)	0.0068 (12)
C6	0.0536 (16)	0.0468 (15)	0.0409 (14)	0.0120 (13)	0.0110 (12)	0.0107 (12)
C7	0.066 (2)	0.082 (2)	0.066 (2)	0.0033 (18)	0.0367 (17)	0.0024 (17)
C8	0.0467 (15)	0.0472 (15)	0.0371 (13)	0.0148 (12)	0.0143 (11)	0.0091 (11)
C9	0.0509 (16)	0.0527 (16)	0.0423 (14)	0.0135 (13)	0.0187 (12)	0.0030 (12)
C10	0.0521 (16)	0.0505 (15)	0.0436 (15)	0.0154 (13)	0.0172 (12)	0.0015 (12)
C11	0.0511 (16)	0.0530 (16)	0.0466 (15)	0.0145 (13)	0.0192 (13)	0.0008 (12)
C12	0.0516 (17)	0.0603 (18)	0.0597 (18)	0.0108 (14)	0.0255 (14)	−0.0024 (14)
C13	0.0455 (16)	0.0543 (17)	0.0610 (18)	0.0055 (13)	0.0174 (14)	−0.0010 (14)
C14	0.0468 (15)	0.0492 (15)	0.0424 (14)	0.0137 (13)	0.0080 (12)	0.0025 (12)
C15	0.067 (2)	0.0493 (17)	0.0566 (18)	0.0091 (15)	0.0084 (15)	−0.0061 (14)
C16	0.0627 (19)	0.0632 (19)	0.0597 (18)	0.0244 (16)	0.0203 (15)	−0.0024 (15)
C17	0.097 (3)	0.0546 (18)	0.063 (2)	0.0304 (18)	0.0367 (19)	0.0014 (15)
C18	0.067 (2)	0.0576 (19)	0.076 (2)	0.0120 (16)	0.0336 (19)	0.0065 (18)
C19	0.114 (4)	0.069 (2)	0.126 (4)	0.039 (2)	0.042 (3)	0.019 (2)
I1	0.06545 (15)	0.05325 (13)	0.06963 (15)	0.00855 (9)	0.03333 (11)	−0.00352 (9)
N1	0.0494 (13)	0.0504 (13)	0.0425 (12)	0.0090 (11)	0.0174 (10)	0.0077 (10)
N2	0.0555 (14)	0.0523 (14)	0.0496 (13)	0.0115 (11)	0.0149 (11)	−0.0053 (11)
O1	0.0943 (17)	0.0500 (12)	0.0587 (13)	0.0227 (12)	0.0266 (12)	−0.0024 (10)
O2	0.121 (3)	0.121 (3)	0.106 (2)	0.028 (2)	0.044 (2)	−0.013 (2)
O3	0.150 (3)	0.093 (2)	0.0662 (17)	0.045 (2)	0.0181 (18)	−0.0002 (15)
S1	0.0494 (4)	0.0476 (4)	0.0501 (4)	0.0109 (3)	0.0197 (3)	−0.0004 (3)
S2	0.0526 (4)	0.0543 (4)	0.0534 (4)	0.0047 (3)	0.0237 (3)	−0.0065 (3)

Geometric parameters (Å, º) top

C1—C2	1.384 (5)	C12—C13	1.372 (4)
C1—C6	1.387 (4)	C12—H12	0.9300
C1—H1	0.9300	C13—C14	1.403 (4)
C2—C3	1.379 (5)	C13—H13	0.9300
C2—H2	0.9300	C14—N2	1.340 (3)
C3—C4	1.379 (5)	C14—S2	1.741 (3)
C3—H3	0.9300	C15—N2	1.459 (4)
C4—C5	1.385 (4)	C15—H15A	0.9600
C4—H4	0.9300	C15—H15B	0.9600
C5—C6	1.391 (4)	C15—H15C	0.9600
C5—S1	1.745 (3)	C16—N2	1.459 (4)
C6—N1	1.401 (3)	C16—C17	1.503 (5)
C7—N1	1.465 (4)	C16—H16A	0.9700
C7—H7A	0.9600	C16—H16B	0.9700
C7—H7B	0.9600	C17—O1	1.439 (4)
C7—H7C	0.9600	C17—H17A	0.9700
C8—N1	1.343 (3)	C17—H17B	0.9700
C8—C9	1.408 (4)	C18—O3	1.196 (4)
C8—S1	1.740 (3)	C18—O1	1.318 (4)
C9—C10	1.362 (4)	C18—C19	1.489 (5)
C9—H9	0.9300	C19—H19A	0.9600
C10—C11	1.387 (4)	C19—H19B	0.9600
C10—H10	0.9300	C19—H19C	0.9600
C11—C12	1.387 (4)	O2—H2A	0.8500
C11—S2	1.752 (3)	O2—H2C	0.8500

C2—C1—C6	117.4 (3)	C14—C13—H13	123.8
C2—C1—H1	121.3	N2—C14—C13	126.6 (3)
C6—C1—H1	121.3	N2—C14—S2	122.6 (2)
C3—C2—C1	121.7 (3)	C13—C14—S2	110.8 (2)
C3—C2—H2	119.2	N2—C15—H15A	109.5
C1—C2—H2	119.2	N2—C15—H15B	109.5
C2—C3—C4	121.1 (3)	H15A—C15—H15B	109.5
C2—C3—H3	119.4	N2—C15—H15C	109.5
C4—C3—H3	119.4	H15A—C15—H15C	109.5
C3—C4—C5	117.8 (3)	H15B—C15—H15C	109.5
C3—C4—H4	121.1	N2—C16—C17	112.6 (3)
C5—C4—H4	121.1	N2—C16—H16A	109.1
C4—C5—C6	121.1 (3)	C17—C16—H16A	109.1
C4—C5—S1	128.1 (3)	N2—C16—H16B	109.1
C6—C5—S1	110.7 (2)	C17—C16—H16B	109.1
C1—C6—C5	120.8 (3)	H16A—C16—H16B	107.8
C1—C6—N1	126.9 (3)	O1—C17—C16	107.5 (2)
C5—C6—N1	112.3 (2)	O1—C17—H17A	110.2
N1—C7—H7A	109.5	C16—C17—H17A	110.2
N1—C7—H7B	109.5	O1—C17—H17B	110.2
H7A—C7—H7B	109.5	C16—C17—H17B	110.2
N1—C7—H7C	109.5	H17A—C17—H17B	108.5
H7A—C7—H7C	109.5	O3—C18—O1	122.8 (3)
H7B—C7—H7C	109.5	O3—C18—C19	125.1 (4)
N1—C8—C9	126.3 (2)	O1—C18—C19	112.2 (3)
N1—C8—S1	111.84 (19)	C18—C19—H19A	109.5
C9—C8—S1	121.9 (2)	C18—C19—H19B	109.5
C10—C9—C8	121.8 (2)	H19A—C19—H19B	109.5
C10—C9—H9	119.1	C18—C19—H19C	109.5
C8—C9—H9	119.1	H19A—C19—H19C	109.5
C9—C10—C11	128.8 (3)	H19B—C19—H19C	109.5
C9—C10—H10	115.6	C8—N1—C6	114.3 (2)
C11—C10—H10	115.6	C8—N1—C7	123.9 (2)
C10—C11—C12	126.4 (3)	C6—N1—C7	121.8 (2)
C10—C11—S2	124.4 (2)	C14—N2—C15	119.5 (3)
C12—C11—S2	109.2 (2)	C14—N2—C16	122.8 (3)
C13—C12—C11	115.8 (3)	C15—N2—C16	117.7 (2)
C13—C12—H12	122.1	C18—O1—C17	117.4 (2)
C11—C12—H12	122.1	H2A—O2—H2C	109.5
C12—C13—C14	112.4 (3)	C8—S1—C5	90.83 (14)
C12—C13—H13	123.8	C14—S2—C11	91.88 (14)

C6—C1—C2—C3	1.2 (5)	C9—C8—N1—C7	−1.4 (4)
C1—C2—C3—C4	−2.0 (6)	S1—C8—N1—C7	178.5 (2)
C2—C3—C4—C5	0.8 (5)	C1—C6—N1—C8	−178.9 (3)
C3—C4—C5—C6	1.1 (4)	C5—C6—N1—C8	1.3 (3)
C3—C4—C5—S1	−179.4 (3)	C1—C6—N1—C7	2.1 (4)
C2—C1—C6—C5	0.6 (4)	C5—C6—N1—C7	−177.7 (3)
C2—C1—C6—N1	−179.2 (3)	C13—C14—N2—C15	3.2 (4)
C4—C5—C6—C1	−1.8 (4)	S2—C14—N2—C15	−178.3 (2)
S1—C5—C6—C1	178.6 (2)	C13—C14—N2—C16	−177.0 (3)
C4—C5—C6—N1	178.0 (3)	S2—C14—N2—C16	1.5 (4)
S1—C5—C6—N1	−1.6 (3)	C17—C16—N2—C14	−105.5 (3)
N1—C8—C9—C10	−179.3 (3)	C17—C16—N2—C15	74.3 (4)
S1—C8—C9—C10	0.7 (4)	O3—C18—O1—C17	−3.4 (5)
C8—C9—C10—C11	179.5 (3)	C19—C18—O1—C17	177.0 (3)
C9—C10—C11—C12	179.7 (3)	C16—C17—O1—C18	−164.4 (3)
C9—C10—C11—S2	−0.9 (5)	N1—C8—S1—C5	−0.4 (2)
C10—C11—C12—C13	179.2 (3)	C9—C8—S1—C5	179.6 (2)
S2—C11—C12—C13	−0.3 (4)	C4—C5—S1—C8	−178.4 (3)
C11—C12—C13—C14	0.8 (4)	C6—C5—S1—C8	1.1 (2)
C12—C13—C14—N2	177.7 (3)	N2—C14—S2—C11	−178.0 (2)
C12—C13—C14—S2	−1.0 (3)	C13—C14—S2—C11	0.7 (2)
N2—C16—C17—O1	61.2 (4)	C10—C11—S2—C14	−179.8 (3)
C9—C8—N1—C6	179.6 (3)	C12—C11—S2—C14	−0.3 (2)
S1—C8—N1—C6	−0.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···I1ⁱ	0.85	2.95	3.647 (3)	140
O2—H2C···O3ⁱⁱ	0.85	2.35	3.056 (5)	140
C7—H7A···O3ⁱ	0.96	2.46	3.364 (5)	157
C19—H19A···O2	0.96	2.60	3.554 (6)	173

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