(1R,3S)-1,1'-(1,3-Dihydro-2-benzofuran-1,3-diyl)bis(1,3-dimethyl-urea).

In the mol-ecule of the title compound, C(14)H(20)N(4)O(3), the five-membered ring adopts an envelope conformation with the O atom displaced by 0.207 (3) Å from the plane of the other ring atoms. Intra-molecular C-H⋯O hydrogen bonds result in the formation of three five-membered rings having envelope conformations. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules, forming R(2) (2)(20) ring motifs, which produce two-dimensional polymeric sheets extending along the b axis. There are also two C-H⋯π inter-actions. The H atoms of one of the methyl groups are disordered over two positions and were refined with occupancies of 0.50.

Related literature

For general background, see: Veeraraghavan et al. (1996 ▶); Lin et al. (2005 ▶); Roy & Sarkar (2005 ▶); Harper et al. (2003 ▶); Tsi & Tan (1997 ▶). For related structures, see: Maliha et al. (2007 ▶, 2009 ▶); Maliha, Hussain et al. (2008 ▶); Maliha, Tariq et al. (2008 ▶). For ring-motifs, see: Bernstein et al. (1995 ▶).For bond lengths and angles in 3-[(2-hydr­oxy-5-nitro­phen­yl)amino]-2-benzofuran-1(3H)-one monohydrate, see: Odabaşoğlu & Büyükgüngör (2006 ▶).

Experimental

Crystal data

C14H20N4O3

M = 292.34

Orthorhombic,

a = 14.6322 (6) Å

b = 9.1014 (3) Å

c = 21.2307 (9) Å

V = 2827.37 (19) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 296 (2) K

0.30 × 0.10 × 0.06 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.982, T max = 0.989

19271 measured reflections

3257 independent reflections

2741 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.150

S = 1.02

3257 reflections

206 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808040828/hk2591sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040828/hk2591Isup2.hkl

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

C14H20N4O3	F(000) = 1008
Mr = 292.34	Dx = 1.374 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2741 reflections
a = 14.6322 (6) Å	θ = 1.9–27.6°
b = 9.1014 (3) Å	µ = 0.10 mm−1
c = 21.2307 (9) Å	T = 296 K
V = 2827.37 (19) Å3	Needle, colorless
Z = 8	0.30 × 0.10 × 0.06 mm

Bruker Kappa APEXII CCD diffractometer	3257 independent reflections
Radiation source: fine-focus sealed tube	2741 reflections with I > 2σ(I)
graphite	Rint = 0.033
Detector resolution: 7.50 pixels mm-1	θmax = 27.6°, θmin = 1.9°
ω scans	h = −18→19
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −11→11
Tmin = 0.982, Tmax = 0.989	l = −27→27
19271 measured reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.1147P)2 + 0.2587P] where P = (Fo2 + 2Fc2)/3
3257 reflections	(Δ/σ)max = 0.001
206 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

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 e.s.d.'s 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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.41467 (6)	0.45600 (11)	0.23235 (4)	0.0174 (3)
O2	0.34799 (7)	0.54659 (10)	0.39413 (5)	0.0198 (3)
O3	0.51470 (7)	0.55115 (10)	0.08040 (4)	0.0182 (3)
N1	0.34567 (8)	0.35646 (12)	0.32370 (5)	0.0172 (3)
N2	0.38830 (8)	0.31870 (14)	0.42697 (5)	0.0192 (3)
N3	0.45143 (8)	0.35663 (12)	0.13270 (5)	0.0166 (3)
N4	0.58841 (8)	0.33324 (13)	0.07804 (6)	0.0184 (3)
C1	0.39065 (9)	0.45278 (15)	0.16603 (6)	0.0158 (4)
C2	0.29157 (9)	0.40893 (14)	0.16576 (6)	0.0156 (4)
C3	0.23533 (9)	0.37551 (15)	0.11520 (7)	0.0190 (4)
C4	0.14426 (10)	0.34209 (16)	0.12735 (7)	0.0216 (4)
C5	0.11093 (9)	0.34332 (15)	0.18873 (7)	0.0202 (4)
C6	0.16762 (9)	0.37606 (15)	0.23927 (7)	0.0183 (4)
C7	0.25847 (9)	0.40992 (15)	0.22654 (6)	0.0157 (4)
C8	0.33352 (9)	0.45371 (15)	0.27125 (6)	0.0161 (3)
C9	0.35403 (9)	0.19953 (15)	0.31148 (6)	0.0180 (4)
C10	0.36122 (9)	0.41503 (15)	0.38270 (6)	0.0163 (4)
C11	0.40137 (10)	0.36344 (17)	0.49181 (7)	0.0229 (4)
C12	0.45527 (10)	0.20371 (14)	0.15296 (7)	0.0187 (4)
C13	0.51929 (9)	0.42070 (14)	0.09633 (6)	0.0151 (3)
C14	0.65525 (9)	0.38690 (17)	0.03293 (7)	0.0216 (4)
H1	0.3955 (12)	0.5527 (19)	0.1483 (8)	0.0190*
H2N	0.4057 (14)	0.238 (2)	0.4170 (9)	0.0287*
H3	0.25789	0.37544	0.07425	0.0228*
H4	0.10534	0.31875	0.09419	0.0259*
H4N	0.5954 (13)	0.244 (2)	0.0902 (9)	0.0276*
H5	0.04970	0.32187	0.19602	0.0243*
H6	0.14554	0.37537	0.28035	0.0220*
H8	0.3231 (12)	0.5534 (18)	0.2901 (8)	0.0193*
H9A	0.32072	0.14578	0.34289	0.0269*
H9B	0.32957	0.17763	0.27058	0.0269*
H9C	0.41729	0.17176	0.31291	0.0269*
H11A	0.37241	0.45675	0.49861	0.0344*	0.500
H11B	0.37481	0.29147	0.51934	0.0344*	0.500
H11C	0.46556	0.37176	0.50047	0.0344*	0.500
H11D	0.43611	0.28991	0.51367	0.0344*	0.500
H11E	0.43371	0.45518	0.49294	0.0344*	0.500
H11F	0.34296	0.37489	0.51181	0.0344*	0.500
H12A	0.49792	0.19423	0.18707	0.0280*
H12B	0.39578	0.17296	0.16673	0.0280*
H12C	0.47463	0.14323	0.11840	0.0280*
H14A	0.68780	0.46846	0.05079	0.0324*
H14B	0.69754	0.30969	0.02295	0.0324*
H14C	0.62456	0.41798	−0.00475	0.0324*

	U11	U22	U33	U12	U13	U23
O1	0.0130 (5)	0.0212 (5)	0.0180 (5)	−0.0019 (3)	0.0006 (3)	−0.0010 (4)
O2	0.0210 (5)	0.0152 (5)	0.0231 (5)	−0.0014 (4)	0.0019 (4)	−0.0037 (4)
O3	0.0177 (5)	0.0155 (5)	0.0214 (5)	−0.0014 (3)	0.0001 (4)	0.0022 (4)
N1	0.0202 (6)	0.0135 (6)	0.0179 (6)	0.0002 (4)	−0.0003 (4)	−0.0011 (4)
N2	0.0206 (6)	0.0189 (6)	0.0180 (6)	0.0029 (4)	−0.0016 (5)	−0.0031 (5)
N3	0.0153 (6)	0.0130 (5)	0.0216 (6)	0.0005 (4)	0.0032 (4)	0.0012 (4)
N4	0.0149 (6)	0.0172 (6)	0.0232 (6)	0.0019 (4)	0.0025 (4)	0.0031 (5)
C1	0.0149 (6)	0.0149 (7)	0.0176 (6)	0.0004 (5)	0.0007 (5)	−0.0003 (5)
C2	0.0144 (6)	0.0121 (6)	0.0204 (7)	0.0015 (5)	0.0001 (5)	0.0008 (5)
C3	0.0189 (7)	0.0185 (7)	0.0195 (6)	0.0014 (5)	−0.0011 (5)	0.0009 (5)
C4	0.0184 (7)	0.0186 (7)	0.0278 (8)	0.0001 (5)	−0.0063 (5)	−0.0010 (6)
C5	0.0131 (6)	0.0157 (7)	0.0318 (8)	−0.0006 (5)	−0.0009 (5)	−0.0009 (5)
C6	0.0167 (7)	0.0145 (6)	0.0238 (7)	0.0002 (5)	0.0037 (5)	0.0001 (5)
C7	0.0151 (6)	0.0111 (6)	0.0209 (7)	0.0009 (5)	0.0002 (5)	0.0001 (5)
C8	0.0136 (6)	0.0154 (6)	0.0193 (6)	−0.0005 (5)	0.0013 (5)	0.0000 (5)
C9	0.0201 (7)	0.0138 (7)	0.0200 (6)	−0.0014 (5)	−0.0013 (5)	−0.0008 (5)
C10	0.0115 (6)	0.0174 (7)	0.0199 (6)	−0.0020 (5)	0.0020 (5)	−0.0017 (5)
C11	0.0233 (7)	0.0261 (8)	0.0194 (7)	−0.0018 (6)	−0.0034 (5)	−0.0018 (5)
C12	0.0198 (7)	0.0138 (7)	0.0224 (6)	0.0007 (5)	0.0031 (5)	0.0016 (5)
C13	0.0136 (6)	0.0154 (6)	0.0162 (6)	−0.0012 (5)	−0.0020 (5)	−0.0003 (5)
C14	0.0157 (7)	0.0251 (8)	0.0240 (7)	−0.0003 (5)	0.0036 (5)	0.0006 (6)

O1—C1	1.4515 (15)	C7—C8	1.5053 (18)
O1—C8	1.4465 (16)	C1—H1	0.987 (17)
O2—C10	1.2370 (16)	C3—H3	0.9300
O3—C13	1.2363 (16)	C4—H4	0.9300
N1—C8	1.4335 (17)	C5—H5	0.9300
N1—C9	1.4568 (17)	C6—H6	0.9300
N1—C10	1.3802 (17)	C8—H8	1.003 (17)
N2—C10	1.3450 (18)	C9—H9A	0.9600
N2—C11	1.4482 (18)	C9—H9B	0.9600
N3—C1	1.4344 (17)	C9—H9C	0.9600
N3—C12	1.4578 (17)	C11—H11A	0.9600
N3—C13	1.3864 (17)	C11—H11B	0.9600
N4—C13	1.3444 (18)	C11—H11C	0.9600
N4—C14	1.4534 (19)	C11—H11D	0.9600
N2—H2N	0.806 (19)	C11—H11E	0.9600
N4—H4N	0.858 (18)	C11—H11F	0.9600
C1—C2	1.5037 (19)	C12—H12A	0.9600
C2—C7	1.3783 (18)	C12—H12B	0.9600
C2—C3	1.3863 (19)	C12—H12C	0.9600
C3—C4	1.391 (2)	C14—H14A	0.9600
C4—C5	1.392 (2)	C14—H14B	0.9600
C5—C6	1.389 (2)	C14—H14C	0.9600
C6—C7	1.3911 (19)
O2···C12i	3.3662 (18)	H1···C4iv	2.734 (17)
O2···N4i	2.8322 (15)	H1···C5iv	2.782 (17)
O3···N2i	2.8229 (16)	H2N···C9	2.390 (19)
O3···C9i	3.2836 (16)	H2N···H9A	2.1700
O1···H5ii	2.7800	H2N···H9C	2.3000
O1···H12A	2.8400	H2N···O3vi	2.062 (19)
O2···H11A	2.3900	H3···H11Bvii	2.5700
O2···H11E	2.5800	H4N···C12	2.473 (19)
O2···H8	2.239 (17)	H4N···H12A	2.5400
O2···H14Aiii	2.7100	H4N···H12C	2.0800
O2···H9Aiv	2.8400	H4N···O2vi	2.006 (18)
O2···H4Ni	2.006 (18)	H5···O1iii	2.7800
O2···H12Ci	2.7500	H5···C9iii	3.0800
O3···H14C	2.7100	H5···H9Ciii	2.3800
O3···H1	2.263 (17)	H6···C9iv	3.0200
O3···H14A	2.7200	H8···O2	2.239 (17)
O3···H2Ni	2.062 (19)	H8···C9iv	2.948 (17)
O3···H9Ci	2.7100	H8···H9Aiv	2.5300
O3···H14Cv	2.6100	H8···H9Biv	2.5400
N2···O3vi	2.8229 (16)	H9A···N2	2.5800
N4···O2vi	2.8322 (15)	H9A···H2N	2.1700
N2···H9A	2.5800	H9A···O2viii	2.8400
N2···H9C	2.8000	H9A···H8viii	2.5300
N3···H11Dvii	2.8700	H9B···C6	3.0500
N4···H12C	2.5500	H9B···C7	2.5400
N4···H11Dvii	2.8400	H9B···H12B	2.4100
C1···C5iv	3.5871 (19)	H9B···C6viii	2.8200
C5···C12iv	3.5034 (19)	H9B···C7viii	2.9100
C5···C1viii	3.5871 (19)	H9B···H8viii	2.5400
C6···C9iv	3.3344 (19)	H9C···N2	2.8000
C6···C9	3.5173 (19)	H9C···H2N	2.3000
C7···C9iv	3.5930 (19)	H9C···O3vi	2.7100
C9···C7viii	3.5930 (19)	H9C···H5ii	2.3800
C9···O3vi	3.2836 (16)	H11A···O2	2.3900
C9···C6viii	3.3344 (19)	H11B···C12ix	3.0700
C9···C6	3.5173 (19)	H11B···H3ix	2.5700
C10···C14iii	3.5153 (19)	H11C···H12Cix	2.5100
C11···C12ix	3.564 (2)	H11D···N3ix	2.8700
C12···O2vi	3.3662 (18)	H11D···N4ix	2.8400
C12···C11vii	3.564 (2)	H11D···C12ix	2.9700
C12···C5viii	3.5034 (19)	H11D···C13ix	2.8700
C14···C10ii	3.5153 (19)	H11D···H12Cix	2.3700
C2···H12B	2.6300	H11E···O2	2.5800
C4···H1viii	2.734 (17)	H11E···C11x	2.9400
C5···H12Biv	3.0400	H11F···C14iii	2.9100
C5···H1viii	2.782 (17)	H11F···H14Biii	2.3300
C6···H9Biv	2.8200	H12A···O1	2.8400
C6···H9B	3.0500	H12A···H4N	2.5400
C7···H9Biv	2.9100	H12B···C2	2.6300
C7···H9B	2.5400	H12B···H9B	2.4100
C9···H8viii	2.948 (17)	H12B···C5viii	3.0400
C9···H5ii	3.0800	H12C···N4	2.5500
C9···H6viii	3.0200	H12C···H4N	2.0800
C9···H2N	2.390 (19)	H12C···O2vi	2.7500
C10···H14Aiii	2.9400	H12C···C11vii	2.8900
C11···H14Biii	3.0400	H12C···H11Cvii	2.5100
C11···H12Cix	2.8900	H12C···H11Dvii	2.3700
C11···H11Ex	2.9400	H14A···O3	2.7200
C12···H11Bvii	3.0700	H14A···O2ii	2.7100
C12···H11Dvii	2.9700	H14A···C10ii	2.9400
C12···H4N	2.473 (19)	H14B···C11ii	3.0400
C13···H11Dvii	2.8700	H14B···H11Fii	2.3300
C14···H11Fii	2.9100	H14C···O3	2.7100
H1···O3	2.263 (17)	H14C···O3v	2.6100
C1—O1—C8	110.78 (9)	C5—C6—H6	121.00
C8—N1—C9	118.52 (10)	C7—C6—H6	121.00
C8—N1—C10	119.14 (11)	O1—C8—H8	109.8 (10)
C9—N1—C10	121.77 (11)	N1—C8—H8	105.5 (10)
C10—N2—C11	121.32 (12)	C7—C8—H8	112.3 (10)
C1—N3—C12	117.44 (11)	N1—C9—H9A	109.00
C1—N3—C13	117.53 (11)	N1—C9—H9B	109.00
C12—N3—C13	122.57 (11)	N1—C9—H9C	109.00
C13—N4—C14	119.84 (12)	H9A—C9—H9B	109.00
C10—N2—H2N	120.3 (14)	H9A—C9—H9C	109.00
C11—N2—H2N	117.7 (14)	H9B—C9—H9C	109.00
C13—N4—H4N	124.3 (13)	N2—C11—H11A	109.00
C14—N4—H4N	115.9 (13)	N2—C11—H11B	109.00
O1—C1—N3	109.92 (10)	N2—C11—H11C	109.00
O1—C1—C2	104.04 (10)	N2—C11—H11D	109.00
N3—C1—C2	115.72 (11)	N2—C11—H11E	109.00
C1—C2—C7	109.48 (11)	N2—C11—H11F	109.00
C3—C2—C7	121.18 (12)	H11A—C11—H11B	109.00
C1—C2—C3	129.31 (12)	H11A—C11—H11C	109.00
C2—C3—C4	118.23 (13)	H11A—C11—H11D	141.00
C3—C4—C5	120.51 (13)	H11A—C11—H11E	56.00
C4—C5—C6	121.07 (13)	H11A—C11—H11F	56.00
C5—C6—C7	117.92 (13)	H11B—C11—H11C	109.00
C2—C7—C8	109.62 (11)	H11B—C11—H11D	56.00
C6—C7—C8	129.29 (12)	H11B—C11—H11E	141.00
C2—C7—C6	121.08 (12)	H11B—C11—H11F	56.00
O1—C8—N1	110.52 (11)	H11C—C11—H11D	56.00
O1—C8—C7	104.04 (10)	H11C—C11—H11E	56.00
N1—C8—C7	114.64 (11)	H11C—C11—H11F	141.00
O2—C10—N1	121.74 (12)	H11D—C11—H11E	109.00
O2—C10—N2	122.68 (12)	H11D—C11—H11F	109.00
N1—C10—N2	115.53 (12)	H11E—C11—H11F	109.00
O3—C13—N4	122.04 (12)	N3—C12—H12A	109.00
N3—C13—N4	116.78 (11)	N3—C12—H12B	109.00
O3—C13—N3	121.16 (12)	N3—C12—H12C	109.00
O1—C1—H1	109.5 (10)	H12A—C12—H12B	109.00
N3—C1—H1	109.2 (10)	H12A—C12—H12C	109.00
C2—C1—H1	108.2 (10)	H12B—C12—H12C	109.00
C2—C3—H3	121.00	N4—C14—H14A	109.00
C4—C3—H3	121.00	N4—C14—H14B	109.00
C3—C4—H4	120.00	N4—C14—H14C	109.00
C5—C4—H4	120.00	H14A—C14—H14B	109.00
C4—C5—H5	119.00	H14A—C14—H14C	109.00
C6—C5—H5	119.00	H14B—C14—H14C	109.00
C8—O1—C1—N3	−138.76 (11)	C14—N4—C13—O3	−6.6 (2)
C8—O1—C1—C2	−14.26 (13)	C14—N4—C13—N3	171.61 (12)
C1—O1—C8—N1	137.61 (11)	O1—C1—C2—C3	−173.35 (13)
C1—O1—C8—C7	14.08 (13)	O1—C1—C2—C7	8.71 (14)
C9—N1—C8—O1	−66.82 (14)	N3—C1—C2—C3	−52.67 (19)
C9—N1—C8—C7	50.35 (16)	N3—C1—C2—C7	129.39 (12)
C10—N1—C8—O1	104.63 (13)	C1—C2—C3—C4	−178.04 (13)
C10—N1—C8—C7	−138.20 (12)	C7—C2—C3—C4	−0.3 (2)
C8—N1—C10—O2	13.95 (19)	C1—C2—C7—C6	178.74 (12)
C8—N1—C10—N2	−168.36 (12)	C1—C2—C7—C8	−0.30 (15)
C9—N1—C10—O2	−174.89 (12)	C3—C2—C7—C6	0.6 (2)
C9—N1—C10—N2	2.80 (18)	C3—C2—C7—C8	−178.44 (12)
C11—N2—C10—O2	1.7 (2)	C2—C3—C4—C5	0.4 (2)
C11—N2—C10—N1	−176.00 (12)	C3—C4—C5—C6	−0.8 (2)
C12—N3—C1—O1	58.72 (15)	C4—C5—C6—C7	1.0 (2)
C12—N3—C1—C2	−58.73 (15)	C5—C6—C7—C2	−0.9 (2)
C13—N3—C1—O1	−103.94 (13)	C5—C6—C7—C8	177.90 (13)
C13—N3—C1—C2	138.62 (12)	C2—C7—C8—O1	−8.26 (14)
C1—N3—C13—O3	−17.51 (18)	C2—C7—C8—N1	−129.07 (12)
C1—N3—C13—N4	164.25 (12)	C6—C7—C8—O1	172.81 (13)
C12—N3—C13—O3	−179.21 (12)	C6—C7—C8—N1	51.99 (19)
C12—N3—C13—N4	2.54 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O3vi	0.806 (19)	2.062 (19)	2.8229 (16)	157.4 (19)
N4—H4N···O2vi	0.858 (18)	2.006 (18)	2.8322 (15)	161.2 (18)
C1—H1···O3	0.987 (17)	2.263 (17)	2.7205 (16)	107.0 (12)
C8—H8···O2	1.003 (17)	2.239 (17)	2.7505 (17)	110.1 (12)
C11—H11A···O2	0.96	2.39	2.7730 (18)	103.0
C9—H9B···CgA	0.96	2.6600	3.0207 (14)	103.0
C12—H12B···CgA	0.96	2.7200	3.0046 (15)	98.0

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O3i	0.806 (19)	2.062 (19)	2.8229 (16)	157.4 (19)
N4—H4N⋯O2i	0.858 (18)	2.006 (18)	2.8322 (15)	161.2 (18)
C1—H1⋯O3	0.987 (17)	2.263 (17)	2.7205 (16)	107.0 (12)
C8—H8⋯O2	1.003 (17)	2.239 (17)	2.7505 (17)	110.1 (12)
C11—H11A⋯O2	0.96	2.39	2.7730 (18)	103.0
C9—H9B⋯CgA	0.96	2.6600	3.0207 (14)	103.0
C12—H12B⋯CgA	0.96	2.7200	3.0046 (15)	98.0

Symmetry code: (i) . CgA is the centroid of the O1/C1/C2/C7/C8 ring.