2,3-Di­phenyl­male­imide 1-methyl­pyrrol­idin-2-one monosolvate

Bulatov, E.; Boyarskaya, D.; Chulkova, T.; Haukka, M.

doi:10.1107/S1600536814002372

organic compounds

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ISSN: 2056-9890

Volume 70| Part 3| March 2014| Page o260

doi:10.1107/S1600536814002372

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2,3-Diphenylmaleimide 1-methylpyrrolidin-2-one monosolvate

Evgeny Bulatov,^a,^b Dina Boyarskaya,^a Tatiana Chulkova ^a ^* and Matti Haukka ^b

^aDepartment of Chemistry, Saint Petersburg State University, Universitetsky Pr. 26, 198504 Stary Petergof, Russian Federation, and ^bDepartment of Chemistry, University of Jyvaskyla, PO Box 35 FI-40014, Jyvaskyla, Finland
^*Correspondence e-mail: t.chulkova@spbu.ru

(Received 7 January 2014; accepted 1 February 2014; online 8 February 2014)

In the title compound, C₁₆H₁₁NO₂·C₅H₉NO, the dihedral angles between the maleimide and phenyl rings are 34.7 (2) and 64.8 (2)°. In the crystal, the 2,3-diphenylmaleimide and 1-methylpyrrolidin-2-one molecules form centrosymmetrical dimers via pairs of strong N—H⋯O hydrogen bonds and π–π stacking interactions between the two neighboring maleimide rings [centroid–centroid distance = 3.495 (2) Å]. The dimers are further linked by weak C—H⋯O and C—H⋯π hydrogen bonds into a three-dimensional framework.

CCDC reference: 978501

Related literature

For general background to maleimides, see: Yeh et al. (2004 ); Billiet et al. (2011 ); Zhu et al. (2012 ); Parsons & Du Bois (2013 ). For the crystal structures of related compounds, see: Zhang et al. (2004 ); Mitzi & Afzali (2007 ).

Experimental

Crystal data

C₁₆H₁₁NO₂·C₅H₉NO
M_r = 348.39
Monoclinic, P 2₁ /n
a = 13.1962 (3) Å
b = 10.0002 (2) Å
c = 13.5600 (3) Å
β = 100.469 (3)°
V = 1759.65 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 170 K
0.54 × 0.40 × 0.24 mm

Data collection

Agilent SuperNova (Single source at offset, Eos) diffractometer
Absorption correction: multi-scan (CrysAlis PRO, Agilent, 2013 ) T_min = 0.815, T_max = 1.000
22206 measured reflections
8818 independent reflections
5708 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.204
S = 1.03
8818 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C3–C8 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3ⁱ	0.88	1.95	2.7800 (15)	156
C5—H5⋯O1ⁱⁱ	0.95	2.41	3.3639 (17)	179
C21—H21A⋯O1ⁱⁱⁱ	0.98	2.59	3.498 (2)	154
C21—H21B⋯O1^iv	0.98	2.73	3.436 (2)	129
C15—H15⋯Cg2^v	0.95	2.96	3.8081 (14)	149
C20—H20A⋯Cg3ⁱⁱⁱ	0.99	2.91	3.6508 (18)	133
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x, y-1, z; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (v) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: CrystalMaker (CrystalMaker, 2011 ); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009 ) and SHELXLE (Hübschle et al., 2011 ).

Supporting information

CCDC reference: 978501

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814002372/kq2011sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814002372/kq2011Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814002372/kq2011Isup3.cml

checkCIF report

Comment top

Maleimide derivatives can be used as building blocks in the synthesis of a wide range of biologically active compounds (Parsons et al., 2013), polymeric materials (Billiet et al., 2011), nanoparticles (Zhu et al., 2012), etc.

The present work describes the synthesis and crystal structure of 2,3-diphenylmaleimide 1-methylpyrrolidin-2-one monosolvate, C₁₆H₁₁NO₂^.C₅H₉NO (Fig. 1). The bond lengths and angles within the 2,3-diphenylmaleimide molecule (Table 1) are in a good agreement with those found in the related compounds (Zhang et al. (2004); Mitzi et al. (2007)). The dihedral angles between the maleimide and phenyl rings are 34.7 (2)° and 64.8 (2)°. In the crystal, the 2,3-diphenylmaleimide and 1-methylpyrrolidin-2-one molecules form centrosymmetrical dimeric associates via strong N—H···O hydrogen bonds (Table 2) and π-π stacking interactions between the two neighboring maleimide rings (the centroid-centroid distance is 3.495 (2) Å). Further the associates are linked by weak C—H···O (Table 2) and C—H···π hydrogen bonds into three-dimensional framework (Fig. 2).

Related literature top

For general background to maleimides, see: Yeh et al. (2004); Billiet et al. (2011); Zhu et al. (2012); Parsons & Du Bois (2013). For the crystal structures of related compounds, see: Zhang et al. (2004); Mitzi & Afzali (2007).

Experimental top

3,4-Diphenylpyrrol-2,5-diimine (0.810 mmol, 0.20 g) was hydrolyzed in 80% aqueous methanol (10 mL) for 24 h at room temperature. The yellow solid was obtained from the reaction mixture. The crystals of the title compound suitable for single crystal X-ray diffraction were obtained by recrystallization from 1-methylpyrrolidin-2-one.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: CrystalMaker (CrystalMaker, 2011); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) and SHELXLE (Hübschle et al., 2011).

Figures top

	Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Crystal packing along the crystallographic a axis. All hydrogen atoms have been omitted for clarity.

2,3-Diphenylmaleimide 1-methylpyrrolidin-2-one monosolvate top

Crystal data top

C₁₆H₁₁NO₂·C₅H₉NO	F(000) = 736
M_r = 348.39	D_x = 1.315 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.1962 (3) Å	Cell parameters from 5604 reflections
b = 10.0002 (2) Å	θ = 3.7–36.7°
c = 13.5600 (3) Å	µ = 0.09 mm⁻¹
β = 100.469 (3)°	T = 170 K
V = 1759.65 (7) Å³	Block, colourless
Z = 4	0.54 × 0.40 × 0.24 mm

Data collection top

Agilent SuperNova (Single source at offset, Eos) diffractometer	8818 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	5708 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.028
Detector resolution: 16.0107 pixels mm^-1	θ_max = 37.5°, θ_min = 3.1°
φ scans and ω scans with κ offset	h = −22→22
Absorption correction: multi-scan (CrysAlis PRO, Agilent, 2013)	k = −13→16
T_min = 0.815, T_max = 1.000	l = −22→23
22206 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.064	H-atom parameters constrained
wR(F²) = 0.204	w = 1/[σ²(F_o²) + (0.0916P)² + 0.4242P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
8818 reflections	Δρ_max = 0.63 e Å⁻³
236 parameters	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₆H₁₁NO₂·C₅H₉NO	V = 1759.65 (7) Å³
M_r = 348.39	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.1962 (3) Å	µ = 0.09 mm⁻¹
b = 10.0002 (2) Å	T = 170 K
c = 13.5600 (3) Å	0.54 × 0.40 × 0.24 mm
β = 100.469 (3)°

Data collection top

Agilent SuperNova (Single source at offset, Eos) diffractometer	8818 independent reflections
Absorption correction: multi-scan (CrysAlis PRO, Agilent, 2013)	5708 reflections with I > 2σ(I)
T_min = 0.815, T_max = 1.000	R_int = 0.028
22206 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.204	H-atom parameters constrained
S = 1.03	Δρ_max = 0.63 e Å⁻³
8818 reflections	Δρ_min = −0.30 e Å⁻³
236 parameters

Special details top

Experimental. Absorption correction: CrysAlis PRO (Agilent, 2013); Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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.

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

	x	y	z	U_iso*/U_eq
O1	0.06128 (8)	0.79304 (9)	0.09092 (7)	0.0333 (2)
O2	0.16449 (8)	0.38928 (10)	−0.01022 (8)	0.0365 (2)
N1	0.10893 (8)	0.60420 (10)	0.01257 (7)	0.0272 (2)
H1	0.1127	0.6383	−0.0465	0.033*
C1	0.13055 (9)	0.47257 (12)	0.04002 (9)	0.0260 (2)
C2	0.10664 (8)	0.45632 (11)	0.14421 (8)	0.0230 (2)
C3	0.12077 (8)	0.33036 (11)	0.20052 (9)	0.0240 (2)
C4	0.09962 (10)	0.20708 (12)	0.15227 (10)	0.0300 (2)
H4	0.0764	0.2042	0.0818	0.036*
C5	0.11244 (11)	0.08926 (13)	0.20683 (12)	0.0366 (3)
H5	0.0982	0.0059	0.1736	0.044*
C6	0.14610 (11)	0.09271 (14)	0.31006 (12)	0.0370 (3)
H6	0.1540	0.0118	0.3473	0.044*
C7	0.16818 (10)	0.21392 (14)	0.35876 (11)	0.0334 (3)
H7	0.1918	0.2160	0.4292	0.040*
C8	0.15569 (9)	0.33222 (13)	0.30448 (9)	0.0275 (2)
H8	0.1709	0.4152	0.3381	0.033*
C9	0.07716 (8)	0.57673 (11)	0.17357 (8)	0.02304 (19)
C10	0.04640 (8)	0.61711 (11)	0.26815 (8)	0.0232 (2)
C11	−0.04123 (10)	0.56355 (15)	0.29686 (10)	0.0324 (3)
H11	−0.0829	0.5013	0.2547	0.039*
C12	−0.06732 (11)	0.60162 (19)	0.38744 (12)	0.0418 (3)
H12	−0.1276	0.5662	0.4067	0.050*
C13	−0.00602 (12)	0.69086 (17)	0.44990 (11)	0.0406 (3)
H13	−0.0241	0.7158	0.5121	0.049*
C14	0.08136 (12)	0.74379 (15)	0.42201 (10)	0.0362 (3)
H14	0.1237	0.8042	0.4653	0.043*
C15	0.10711 (10)	0.70841 (13)	0.33056 (9)	0.0290 (2)
H15	0.1661	0.7465	0.3105	0.035*
C16	0.08056 (9)	0.67456 (12)	0.09100 (9)	0.0254 (2)
O3	0.67483 (9)	0.76077 (11)	0.35649 (9)	0.0429 (3)
N2	0.65279 (9)	0.53588 (12)	0.32844 (9)	0.0348 (2)
C17	0.66039 (10)	0.66246 (14)	0.30065 (11)	0.0333 (3)
C18	0.64860 (19)	0.66600 (18)	0.18720 (12)	0.0554 (5)
H18A	0.5915	0.7263	0.1580	0.066*
H18B	0.7129	0.6983	0.1672	0.066*
C19	0.62610 (16)	0.52685 (18)	0.15209 (12)	0.0483 (4)
H19A	0.6767	0.4966	0.1112	0.058*
H19B	0.5562	0.5208	0.1109	0.058*
C20	0.63358 (14)	0.44090 (16)	0.24659 (13)	0.0447 (4)
H20A	0.5685	0.3917	0.2467	0.054*
H20B	0.6908	0.3758	0.2514	0.054*
C21	0.65804 (14)	0.4951 (2)	0.43134 (12)	0.0479 (4)
H21A	0.5906	0.4613	0.4404	0.072*
H21B	0.6773	0.5719	0.4757	0.072*
H21C	0.7098	0.4244	0.4478	0.072*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0447 (5)	0.0228 (4)	0.0320 (4)	0.0014 (4)	0.0059 (4)	0.0003 (3)
O2	0.0443 (5)	0.0350 (5)	0.0337 (5)	0.0028 (4)	0.0161 (4)	−0.0076 (4)
N1	0.0337 (5)	0.0265 (5)	0.0219 (4)	−0.0021 (4)	0.0062 (4)	−0.0016 (4)
C1	0.0263 (5)	0.0271 (5)	0.0247 (5)	−0.0012 (4)	0.0050 (4)	−0.0041 (4)
C2	0.0235 (4)	0.0221 (5)	0.0232 (4)	−0.0005 (3)	0.0039 (4)	−0.0028 (4)
C3	0.0219 (4)	0.0218 (4)	0.0283 (5)	0.0014 (4)	0.0046 (4)	−0.0026 (4)
C4	0.0304 (5)	0.0230 (5)	0.0355 (6)	0.0006 (4)	0.0028 (5)	−0.0054 (4)
C5	0.0329 (6)	0.0221 (5)	0.0536 (8)	0.0002 (4)	0.0049 (6)	−0.0022 (5)
C6	0.0316 (6)	0.0278 (6)	0.0515 (8)	0.0042 (5)	0.0074 (6)	0.0094 (6)
C7	0.0300 (5)	0.0358 (6)	0.0341 (6)	0.0071 (5)	0.0047 (5)	0.0060 (5)
C8	0.0277 (5)	0.0254 (5)	0.0292 (5)	0.0035 (4)	0.0040 (4)	−0.0002 (4)
C9	0.0242 (4)	0.0219 (4)	0.0230 (4)	−0.0008 (4)	0.0043 (4)	−0.0018 (4)
C10	0.0249 (4)	0.0219 (4)	0.0234 (4)	0.0016 (4)	0.0054 (4)	−0.0007 (4)
C11	0.0268 (5)	0.0382 (7)	0.0331 (6)	−0.0036 (5)	0.0077 (4)	−0.0008 (5)
C12	0.0332 (6)	0.0589 (10)	0.0371 (7)	−0.0004 (6)	0.0163 (5)	0.0034 (7)
C13	0.0460 (8)	0.0513 (9)	0.0275 (6)	0.0078 (6)	0.0148 (6)	−0.0004 (6)
C14	0.0479 (7)	0.0354 (7)	0.0258 (5)	−0.0018 (6)	0.0083 (5)	−0.0061 (5)
C15	0.0345 (6)	0.0270 (5)	0.0264 (5)	−0.0047 (4)	0.0081 (4)	−0.0038 (4)
C16	0.0275 (5)	0.0244 (5)	0.0239 (5)	−0.0018 (4)	0.0036 (4)	−0.0020 (4)
O3	0.0568 (6)	0.0368 (5)	0.0397 (5)	−0.0118 (5)	0.0214 (5)	−0.0127 (4)
N2	0.0366 (5)	0.0342 (6)	0.0347 (6)	−0.0033 (4)	0.0091 (4)	−0.0007 (5)
C17	0.0317 (5)	0.0324 (6)	0.0368 (6)	−0.0018 (5)	0.0085 (5)	−0.0040 (5)
C18	0.0896 (14)	0.0413 (9)	0.0326 (7)	−0.0106 (9)	0.0043 (8)	0.0021 (6)
C19	0.0630 (10)	0.0473 (9)	0.0359 (7)	−0.0088 (8)	0.0126 (7)	−0.0103 (7)
C20	0.0566 (9)	0.0310 (7)	0.0478 (8)	−0.0027 (6)	0.0134 (7)	−0.0093 (6)
C21	0.0487 (8)	0.0598 (10)	0.0359 (7)	−0.0088 (8)	0.0098 (6)	0.0105 (7)

Geometric parameters (Å, º) top

O1—C16	1.2118 (15)	C11—H11	0.9500
O2—C1	1.2121 (15)	C12—C13	1.385 (2)
N1—C16	1.3824 (15)	C12—H12	0.9500
N1—C1	1.3835 (16)	C13—C14	1.383 (2)
N1—H1	0.8800	C13—H13	0.9500
C1—C2	1.5113 (16)	C14—C15	1.3898 (18)
C2—C9	1.3476 (16)	C14—H14	0.9500
C2—C3	1.4672 (16)	C15—H15	0.9500
C3—C4	1.3998 (16)	O3—C17	1.2344 (17)
C3—C8	1.4013 (17)	N2—C17	1.3296 (19)
C4—C5	1.3851 (19)	N2—C21	1.4433 (19)
C4—H4	0.9500	N2—C20	1.448 (2)
C5—C6	1.390 (2)	C17—C18	1.518 (2)
C5—H5	0.9500	C18—C19	1.483 (2)
C6—C7	1.386 (2)	C18—H18A	0.9900
C6—H6	0.9500	C18—H18B	0.9900
C7—C8	1.3872 (18)	C19—C20	1.531 (2)
C7—H7	0.9500	C19—H19A	0.9900
C8—H8	0.9500	C19—H19B	0.9900
C9—C10	1.4703 (15)	C20—H20A	0.9900
C9—C16	1.4936 (16)	C20—H20B	0.9900
C10—C11	1.3926 (17)	C21—H21A	0.9800
C10—C15	1.3947 (16)	C21—H21B	0.9800
C11—C12	1.388 (2)	C21—H21C	0.9800

C16—N1—C1	110.41 (10)	C12—C13—H13	119.9
C16—N1—H1	124.8	C13—C14—C15	119.86 (13)
C1—N1—H1	124.8	C13—C14—H14	120.1
O2—C1—N1	125.57 (12)	C15—C14—H14	120.1
O2—C1—C2	127.79 (12)	C14—C15—C10	120.10 (12)
N1—C1—C2	106.62 (10)	C14—C15—H15	120.0
C9—C2—C3	129.02 (11)	C10—C15—H15	120.0
C9—C2—C1	107.49 (10)	O1—C16—N1	125.67 (12)
C3—C2—C1	123.40 (10)	O1—C16—C9	127.31 (11)
C4—C3—C8	118.88 (11)	N1—C16—C9	107.01 (10)
C4—C3—C2	121.14 (11)	C17—N2—C21	123.38 (14)
C8—C3—C2	119.97 (10)	C17—N2—C20	114.78 (13)
C5—C4—C3	120.32 (13)	C21—N2—C20	121.78 (14)
C5—C4—H4	119.8	O3—C17—N2	126.55 (14)
C3—C4—H4	119.8	O3—C17—C18	125.38 (14)
C4—C5—C6	120.16 (13)	N2—C17—C18	108.07 (13)
C4—C5—H5	119.9	C19—C18—C17	106.32 (14)
C6—C5—H5	119.9	C19—C18—H18A	110.5
C7—C6—C5	120.18 (13)	C17—C18—H18A	110.5
C7—C6—H6	119.9	C19—C18—H18B	110.5
C5—C6—H6	119.9	C17—C18—H18B	110.5
C6—C7—C8	119.91 (13)	H18A—C18—H18B	108.7
C6—C7—H7	120.0	C18—C19—C20	106.22 (13)
C8—C7—H7	120.0	C18—C19—H19A	110.5
C7—C8—C3	120.54 (12)	C20—C19—H19A	110.5
C7—C8—H8	119.7	C18—C19—H19B	110.5
C3—C8—H8	119.7	C20—C19—H19B	110.5
C2—C9—C10	130.04 (11)	H19A—C19—H19B	108.7
C2—C9—C16	108.31 (10)	N2—C20—C19	104.41 (13)
C10—C9—C16	121.64 (10)	N2—C20—H20A	110.9
C11—C10—C15	119.78 (11)	C19—C20—H20A	110.9
C11—C10—C9	120.87 (11)	N2—C20—H20B	110.9
C15—C10—C9	119.33 (10)	C19—C20—H20B	110.9
C12—C11—C10	119.61 (13)	H20A—C20—H20B	108.9
C12—C11—H11	120.2	N2—C21—H21A	109.5
C10—C11—H11	120.2	N2—C21—H21B	109.5
C13—C12—C11	120.44 (13)	H21A—C21—H21B	109.5
C13—C12—H12	119.8	N2—C21—H21C	109.5
C11—C12—H12	119.8	H21A—C21—H21C	109.5
C14—C13—C12	120.19 (13)	H21B—C21—H21C	109.5
C14—C13—H13	119.9

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C3–C8 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.88	1.95	2.7800 (15)	156
C5—H5···O1ⁱⁱ	0.95	2.41	3.3639 (17)	179
C21—H21A···O1ⁱⁱⁱ	0.98	2.59	3.498 (2)	154
C21—H21B···O1^iv	0.98	2.73	3.436 (2)	129
C15—H15···Cg2^v	0.95	2.96	3.8081 (14)	149
C20—H20A···Cg3ⁱⁱⁱ	0.99	2.91	3.6508 (18)	133

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

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C3–C8 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.88	1.95	2.7800 (15)	156.0
C5—H5···O1ⁱⁱ	0.95	2.41	3.3639 (17)	179.3
C21—H21A···O1ⁱⁱⁱ	0.98	2.59	3.498 (2)	153.6
C21—H21B···O1^iv	0.98	2.73	3.436 (2)	128.9
C15—H15···Cg2^v	0.95	2.96	3.8081 (14)	149
C20—H20A···Cg3ⁱⁱⁱ	0.99	2.91	3.6508 (18)	133

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

Acknowledgements

The authors are obliged to the Ministry of Education and Science of the Russian Federation for the Scholarship of the President of the Russian Federation for Students and PhD Students Training Abroad (2013–2014).

References

Agilent (2013). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Billiet, L., Gok, O., Dove, A. P., Sanyal, A., Nguyen, L.-T. T. & Du Prez, F. E. (2011). Macromolecules, 44, 7874–7878. Web of Science CrossRef CAS Google Scholar
CrystalMaker (2011). CrystalMaker. CrystalMaker Software Ltd, Yarnton, England. Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Hübschle, C. B., Sheldrick, G. M. & Dittrich, B. (2011). J. Appl. Cryst. 44, 1281–1284. Web of Science CrossRef IUCr Journals Google Scholar
Mitzi, D. B. & Afzali, A. (2007). Cryst. Growth Des. 7, 691–697. Web of Science CSD CrossRef CAS Google Scholar
Parsons, W. H. & Du Bois, J. (2013). J. Am. Chem. Soc. 135, 10582–10585. Web of Science CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yeh, H.-C., Wu, W.-C., Wen, Y.-S., Dai, D.-C., Wang, J.-K. & Chen, C.-T. (2004). J. Org. Chem. 69, 6455–6462. Web of Science CSD CrossRef PubMed CAS Google Scholar
Zhang, Z.-Q., Uth, S., Sandman, D. J. & Foxman, B. M. (2004). J. Phys. Org. Chem. 17, 769–776. Web of Science CSD CrossRef CAS Google Scholar
Zhu, J., Waengler, C., Lennox, R. B. & Schirrmacher, R. (2012). Langmuir, 28, 5508–5512. Web of Science CrossRef CAS PubMed Google Scholar

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