4-Chloro-N-[(E)-(3,4-dimeth-oxy-phen-yl)methyl-idene]aniline.

The asymmetric unit of the title compound, C(15)H(14)ClNO(2), contains two mol-ecules with significantly different conformations: the dihedral angles between the 4-chloro-aniline and 3,4-dimeth-oxy-phenyl (excluding C atoms) moieties are 19.68 (7) and 45.54 (4)°. In the crystal, the mol-ecules are linked by C-H⋯O hydrogen bonds and weak C-H⋯π inter-actions.

Related literature

For related structures, see: Dehno Khalaji et al. (2009 ▶); Shang & Tan (2007 ▶).

Experimental

Crystal data

C15H14ClNO2

M = 275.72

Monoclinic,

a = 12.4227 (4) Å

b = 7.3638 (2) Å

c = 30.4583 (13) Å

β = 96.080 (2)°

V = 2770.60 (17) Å3

Z = 8

Mo Kα radiation

μ = 0.27 mm−1

T = 296 K

0.35 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.932, T max = 0.950

20975 measured reflections

5007 independent reflections

3456 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.120

S = 1.05

5007 reflections

347 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810032782/hb5610sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032782/hb5610Isup2.hkl

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

C15H14ClNO2	F(000) = 1152
Mr = 275.72	Dx = 1.322 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3456 reflections
a = 12.4227 (4) Å	θ = 1.7–25.3°
b = 7.3638 (2) Å	µ = 0.27 mm−1
c = 30.4583 (13) Å	T = 296 K
β = 96.080 (2)°	Prism, light yellow
V = 2770.60 (17) Å3	0.35 × 0.22 × 0.20 mm
Z = 8

Bruker Kappa APEXII CCD diffractometer	5007 independent reflections
Radiation source: fine-focus sealed tube	3456 reflections with I > 2σ(I)
graphite	Rint = 0.026
Detector resolution: 8.10 pixels mm-1	θmax = 25.3°, θmin = 1.7°
ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −8→8
Tmin = 0.932, Tmax = 0.950	l = −36→29
20975 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0465P)2 + 1.0036P] where P = (Fo2 + 2Fc2)/3
5007 reflections	(Δ/σ)max < 0.001
347 parameters	Δρmax = 0.19 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
Cl1	−0.47381 (6)	0.59742 (12)	0.19551 (3)	0.1029 (3)
O1	0.34541 (11)	0.7300 (2)	0.00839 (5)	0.0666 (6)
O2	0.15540 (11)	0.7756 (2)	−0.03006 (4)	0.0622 (5)
N1	−0.10335 (14)	0.6680 (2)	0.09001 (5)	0.0531 (6)
C1	−0.18906 (15)	0.6522 (3)	0.11683 (6)	0.0480 (6)
C2	−0.27949 (16)	0.5526 (3)	0.10049 (7)	0.0534 (7)
C3	−0.36655 (17)	0.5352 (3)	0.12478 (7)	0.0582 (8)
C4	−0.36430 (18)	0.6199 (3)	0.16498 (8)	0.0597 (8)
C5	−0.27691 (19)	0.7213 (3)	0.18141 (7)	0.0641 (8)
C6	−0.18948 (17)	0.7378 (3)	0.15726 (7)	0.0572 (8)
C7	−0.00599 (17)	0.6629 (3)	0.10774 (7)	0.0547 (7)
C8	0.08663 (16)	0.6815 (3)	0.08263 (7)	0.0505 (7)
C9	0.07247 (15)	0.7174 (3)	0.03730 (6)	0.0481 (7)
C10	0.15987 (16)	0.7355 (3)	0.01380 (6)	0.0477 (6)
C11	0.26563 (16)	0.7137 (3)	0.03515 (7)	0.0505 (7)
C12	0.27930 (17)	0.6779 (3)	0.07967 (7)	0.0595 (8)
C13	0.19067 (17)	0.6630 (3)	0.10334 (7)	0.0606 (8)
C14	0.45431 (17)	0.7121 (4)	0.02793 (9)	0.0797 (10)
C15	0.05181 (18)	0.8106 (4)	−0.05280 (7)	0.0704 (9)
Cl2	−0.28854 (6)	0.13333 (12)	0.26687 (2)	0.0916 (3)
O3	0.34354 (11)	0.2151 (2)	0.04035 (5)	0.0685 (6)
O4	0.53216 (11)	0.1383 (2)	0.07674 (5)	0.0614 (5)
N2	0.08863 (14)	0.1523 (2)	0.16357 (6)	0.0538 (6)
C16	0.00252 (16)	0.1438 (3)	0.19048 (6)	0.0474 (7)
C17	−0.09141 (16)	0.2363 (3)	0.17535 (7)	0.0526 (7)
C18	−0.18002 (17)	0.2347 (3)	0.19879 (7)	0.0575 (7)
C19	−0.17623 (17)	0.1391 (3)	0.23760 (7)	0.0535 (7)
C20	−0.08492 (18)	0.0463 (3)	0.25324 (7)	0.0614 (8)
C21	0.00371 (17)	0.0481 (3)	0.22977 (7)	0.0572 (7)
C22	0.18473 (17)	0.1189 (3)	0.17922 (7)	0.0597 (8)
C23	0.27594 (16)	0.1226 (3)	0.15321 (7)	0.0547 (7)
C24	0.26207 (16)	0.1687 (3)	0.10854 (7)	0.0511 (7)
C25	0.34811 (16)	0.1725 (3)	0.08394 (7)	0.0502 (7)
C26	0.45269 (15)	0.1286 (3)	0.10403 (7)	0.0515 (7)
C27	0.46640 (17)	0.0814 (3)	0.14774 (8)	0.0654 (8)
C28	0.37878 (18)	0.0795 (4)	0.17212 (8)	0.0700 (9)
C29	0.23950 (17)	0.2317 (3)	0.01634 (7)	0.0672 (8)
C30	0.63635 (16)	0.0663 (3)	0.09192 (8)	0.0675 (9)
H2	−0.28136	0.49722	0.07297	0.0640*
H3	−0.42638	0.46651	0.11397	0.0699*
H5	−0.27641	0.77864	0.20863	0.0769*
H6	−0.13016	0.80729	0.16828	0.0686*
H7	0.00653	0.64637	0.13813	0.0656*
H9	0.00291	0.72905	0.02296	0.0577*
H12	0.34870	0.66362	0.09400	0.0714*
H13	0.20112	0.64022	0.13353	0.0727*
H14A	0.46754	0.79754	0.05169	0.1193*
H14B	0.50294	0.73565	0.00611	0.1193*
H14C	0.46581	0.59102	0.03914	0.1193*
H15A	0.00931	0.70152	−0.05403	0.1056*
H15B	0.05986	0.85091	−0.08225	0.1056*
H15C	0.01616	0.90321	−0.03750	0.1056*
H17	−0.09447	0.30033	0.14893	0.0631*
H18	−0.24229	0.29817	0.18840	0.0690*
H20	−0.08271	−0.01779	0.27963	0.0737*
H21	0.06554	−0.01593	0.24041	0.0687*
H22	0.19776	0.09042	0.20906	0.0716*
H24	0.19328	0.19723	0.09526	0.0614*
H27	0.53481	0.05060	0.16104	0.0785*
H28	0.38922	0.04869	0.20187	0.0840*
H29A	0.19869	0.12289	0.01982	0.1007*
H29B	0.24729	0.24997	−0.01437	0.1007*
H29C	0.20224	0.33350	0.02736	0.1007*
H30A	0.66641	0.13300	0.11741	0.1012*
H30B	0.68330	0.07689	0.06896	0.1012*
H30C	0.62931	−0.05923	0.09960	0.1012*

	U11	U22	U33	U12	U13	U23
Cl1	0.0819 (5)	0.1266 (7)	0.1086 (6)	0.0040 (4)	0.0499 (4)	0.0131 (5)
O1	0.0419 (8)	0.0932 (12)	0.0652 (10)	−0.0014 (8)	0.0074 (7)	0.0011 (9)
O2	0.0502 (8)	0.0884 (11)	0.0482 (8)	0.0024 (8)	0.0058 (7)	0.0031 (8)
N1	0.0510 (10)	0.0576 (10)	0.0509 (10)	−0.0004 (8)	0.0067 (8)	0.0022 (8)
C1	0.0490 (11)	0.0469 (11)	0.0480 (11)	0.0033 (9)	0.0048 (9)	0.0062 (9)
C2	0.0576 (13)	0.0507 (12)	0.0512 (12)	0.0006 (10)	0.0028 (10)	0.0015 (10)
C3	0.0496 (12)	0.0575 (13)	0.0664 (14)	−0.0020 (10)	0.0005 (10)	0.0109 (11)
C4	0.0568 (13)	0.0607 (14)	0.0640 (14)	0.0086 (11)	0.0179 (11)	0.0117 (11)
C5	0.0749 (16)	0.0635 (14)	0.0554 (13)	0.0048 (12)	0.0139 (12)	−0.0054 (11)
C6	0.0574 (13)	0.0566 (13)	0.0572 (13)	−0.0035 (10)	0.0045 (10)	−0.0052 (10)
C7	0.0574 (13)	0.0604 (13)	0.0464 (11)	0.0015 (10)	0.0059 (10)	0.0051 (10)
C8	0.0492 (12)	0.0535 (12)	0.0487 (11)	0.0007 (9)	0.0043 (9)	0.0026 (9)
C9	0.0419 (11)	0.0496 (12)	0.0518 (12)	0.0011 (9)	0.0001 (9)	−0.0002 (9)
C10	0.0482 (11)	0.0469 (11)	0.0472 (11)	0.0005 (9)	0.0015 (9)	−0.0022 (9)
C11	0.0450 (11)	0.0514 (12)	0.0548 (12)	−0.0009 (9)	0.0043 (9)	−0.0033 (10)
C12	0.0438 (11)	0.0724 (15)	0.0601 (14)	0.0015 (10)	−0.0049 (10)	−0.0011 (11)
C13	0.0588 (13)	0.0740 (15)	0.0478 (12)	0.0017 (11)	0.0000 (10)	0.0064 (11)
C14	0.0445 (13)	0.113 (2)	0.0814 (17)	−0.0016 (13)	0.0054 (12)	−0.0137 (16)
C15	0.0656 (15)	0.0966 (18)	0.0477 (12)	0.0126 (13)	0.0000 (11)	−0.0030 (12)
Cl2	0.0734 (4)	0.1239 (6)	0.0828 (5)	0.0051 (4)	0.0329 (3)	−0.0075 (4)
O3	0.0441 (8)	0.1016 (12)	0.0596 (9)	0.0077 (8)	0.0045 (7)	0.0180 (9)
O4	0.0406 (8)	0.0748 (10)	0.0686 (10)	0.0043 (7)	0.0045 (7)	0.0094 (8)
N2	0.0529 (10)	0.0587 (11)	0.0503 (10)	0.0024 (8)	0.0072 (8)	0.0034 (8)
C16	0.0516 (12)	0.0447 (11)	0.0452 (11)	0.0001 (9)	0.0023 (9)	−0.0007 (9)
C17	0.0593 (13)	0.0538 (12)	0.0432 (11)	0.0071 (10)	−0.0019 (9)	0.0047 (9)
C18	0.0528 (12)	0.0617 (13)	0.0562 (13)	0.0120 (10)	−0.0030 (10)	−0.0051 (11)
C19	0.0538 (12)	0.0565 (12)	0.0509 (12)	0.0000 (10)	0.0094 (10)	−0.0085 (10)
C20	0.0689 (15)	0.0616 (14)	0.0543 (13)	0.0024 (11)	0.0092 (11)	0.0119 (11)
C21	0.0549 (12)	0.0573 (13)	0.0586 (13)	0.0091 (10)	0.0021 (10)	0.0126 (11)
C22	0.0588 (14)	0.0723 (15)	0.0474 (12)	0.0005 (11)	0.0035 (10)	0.0030 (11)
C23	0.0500 (12)	0.0606 (13)	0.0531 (12)	0.0010 (10)	0.0031 (10)	0.0013 (10)
C24	0.0425 (11)	0.0537 (12)	0.0564 (12)	0.0045 (9)	0.0016 (9)	0.0031 (10)
C25	0.0471 (11)	0.0496 (12)	0.0531 (12)	0.0015 (9)	0.0011 (9)	0.0050 (10)
C26	0.0423 (11)	0.0512 (12)	0.0600 (13)	0.0006 (9)	0.0005 (9)	0.0018 (10)
C27	0.0440 (12)	0.0853 (17)	0.0642 (14)	0.0044 (11)	−0.0073 (10)	0.0105 (12)
C28	0.0580 (14)	0.0963 (18)	0.0538 (13)	0.0041 (12)	−0.0028 (11)	0.0113 (13)
C29	0.0576 (13)	0.0810 (16)	0.0606 (14)	0.0047 (12)	−0.0046 (11)	0.0085 (12)
C30	0.0416 (12)	0.0733 (15)	0.0867 (17)	0.0067 (10)	0.0029 (11)	0.0070 (13)

Cl1—C4	1.735 (2)	C13—H13	0.9300
Cl2—C19	1.734 (2)	C14—H14A	0.9600
O1—C11	1.354 (2)	C14—H14B	0.9600
O1—C14	1.425 (3)	C14—H14C	0.9600
O2—C15	1.419 (3)	C15—H15A	0.9600
O2—C10	1.364 (2)	C15—H15B	0.9600
O3—C25	1.360 (3)	C15—H15C	0.9600
O3—C29	1.421 (3)	C16—C17	1.387 (3)
O4—C30	1.430 (3)	C16—C21	1.388 (3)
O4—C26	1.358 (2)	C17—C18	1.374 (3)
N1—C7	1.272 (3)	C18—C19	1.372 (3)
N1—C1	1.414 (2)	C19—C20	1.366 (3)
N2—C22	1.262 (3)	C20—C21	1.375 (3)
N2—C16	1.416 (3)	C22—C23	1.450 (3)
C1—C6	1.384 (3)	C23—C24	1.395 (3)
C1—C2	1.389 (3)	C23—C28	1.382 (3)
C2—C3	1.380 (3)	C24—C25	1.369 (3)
C3—C4	1.372 (3)	C25—C26	1.414 (3)
C4—C5	1.368 (3)	C26—C27	1.369 (3)
C5—C6	1.380 (3)	C27—C28	1.381 (3)
C7—C8	1.454 (3)	C17—H17	0.9300
C8—C9	1.398 (3)	C18—H18	0.9300
C8—C13	1.384 (3)	C20—H20	0.9300
C9—C10	1.369 (3)	C21—H21	0.9300
C10—C11	1.412 (3)	C22—H22	0.9300
C11—C12	1.374 (3)	C24—H24	0.9300
C12—C13	1.383 (3)	C27—H27	0.9300
C2—H2	0.9300	C28—H28	0.9300
C3—H3	0.9300	C29—H29A	0.9600
C5—H5	0.9300	C29—H29B	0.9600
C6—H6	0.9300	C29—H29C	0.9600
C7—H7	0.9300	C30—H30A	0.9600
C9—H9	0.9300	C30—H30B	0.9600
C12—H12	0.9300	C30—H30C	0.9600
C11—O1—C14	117.62 (17)	H15A—C15—H15B	109.00
C10—O2—C15	117.28 (15)	O2—C15—H15A	109.00
C25—O3—C29	117.64 (16)	O2—C15—H15B	109.00
C26—O4—C30	118.33 (17)	N2—C16—C17	116.51 (17)
C1—N1—C7	119.52 (17)	N2—C16—C21	125.58 (19)
C16—N2—C22	121.01 (18)	C17—C16—C21	117.89 (19)
N1—C1—C6	123.42 (18)	C16—C17—C18	121.0 (2)
N1—C1—C2	117.81 (17)	C17—C18—C19	119.7 (2)
C2—C1—C6	118.70 (18)	Cl2—C19—C18	119.96 (17)
C1—C2—C3	120.48 (19)	Cl2—C19—C20	119.48 (17)
C2—C3—C4	119.6 (2)	C18—C19—C20	120.6 (2)
C3—C4—C5	121.0 (2)	C19—C20—C21	119.7 (2)
Cl1—C4—C3	119.47 (17)	C16—C21—C20	121.2 (2)
Cl1—C4—C5	119.53 (18)	N2—C22—C23	123.6 (2)
C4—C5—C6	119.5 (2)	C22—C23—C24	120.96 (18)
C1—C6—C5	120.8 (2)	C22—C23—C28	120.6 (2)
N1—C7—C8	122.94 (19)	C24—C23—C28	118.41 (19)
C7—C8—C9	120.89 (18)	C23—C24—C25	121.05 (19)
C7—C8—C13	120.26 (19)	O3—C25—C24	125.80 (19)
C9—C8—C13	118.85 (19)	O3—C25—C26	114.64 (17)
C8—C9—C10	120.72 (18)	C24—C25—C26	119.57 (19)
O2—C10—C11	114.53 (17)	O4—C26—C25	114.67 (18)
O2—C10—C9	125.53 (18)	O4—C26—C27	125.80 (18)
C9—C10—C11	119.93 (17)	C25—C26—C27	119.54 (19)
O1—C11—C10	114.68 (18)	C26—C27—C28	120.1 (2)
O1—C11—C12	126.11 (19)	C23—C28—C27	121.3 (2)
C10—C11—C12	119.21 (19)	C16—C17—H17	119.00
C11—C12—C13	120.5 (2)	C18—C17—H17	119.00
C8—C13—C12	120.8 (2)	C17—C18—H18	120.00
C1—C2—H2	120.00	C19—C18—H18	120.00
C3—C2—H2	120.00	C19—C20—H20	120.00
C2—C3—H3	120.00	C21—C20—H20	120.00
C4—C3—H3	120.00	C16—C21—H21	119.00
C4—C5—H5	120.00	C20—C21—H21	119.00
C6—C5—H5	120.00	N2—C22—H22	118.00
C1—C6—H6	120.00	C23—C22—H22	118.00
C5—C6—H6	120.00	C23—C24—H24	119.00
C8—C7—H7	119.00	C25—C24—H24	119.00
N1—C7—H7	119.00	C26—C27—H27	120.00
C8—C9—H9	120.00	C28—C27—H27	120.00
C10—C9—H9	120.00	C23—C28—H28	119.00
C11—C12—H12	120.00	C27—C28—H28	119.00
C13—C12—H12	120.00	O3—C29—H29A	109.00
C12—C13—H13	120.00	O3—C29—H29B	109.00
C8—C13—H13	120.00	O3—C29—H29C	109.00
O1—C14—H14B	109.00	H29A—C29—H29B	109.00
H14A—C14—H14C	109.00	H29A—C29—H29C	109.00
O1—C14—H14C	109.00	H29B—C29—H29C	109.00
H14A—C14—H14B	109.00	O4—C30—H30A	109.00
O1—C14—H14A	109.00	O4—C30—H30B	109.00
H14B—C14—H14C	109.00	O4—C30—H30C	109.00
O2—C15—H15C	109.00	H30A—C30—H30B	109.00
H15A—C15—H15C	109.00	H30A—C30—H30C	109.00
H15B—C15—H15C	109.00	H30B—C30—H30C	110.00
C14—O1—C11—C10	179.1 (2)	O2—C10—C11—O1	−2.1 (3)
C14—O1—C11—C12	−1.3 (3)	O2—C10—C11—C12	178.25 (19)
C15—O2—C10—C9	3.4 (3)	C9—C10—C11—O1	178.4 (2)
C15—O2—C10—C11	−176.1 (2)	C9—C10—C11—C12	−1.3 (3)
C29—O3—C25—C26	169.99 (18)	O1—C11—C12—C13	−179.5 (2)
C29—O3—C25—C24	−9.7 (3)	C10—C11—C12—C13	0.1 (3)
C30—O4—C26—C25	−169.27 (18)	C11—C12—C13—C8	0.8 (3)
C30—O4—C26—C27	10.8 (3)	N2—C16—C17—C18	179.24 (19)
C1—N1—C7—C8	−178.84 (19)	C21—C16—C17—C18	0.7 (3)
C7—N1—C1—C6	41.7 (3)	N2—C16—C21—C20	−179.1 (2)
C7—N1—C1—C2	−141.6 (2)	C17—C16—C21—C20	−0.6 (3)
C22—N2—C16—C21	−21.7 (3)	C16—C17—C18—C19	−0.5 (3)
C16—N2—C22—C23	179.0 (2)	C17—C18—C19—Cl2	−178.91 (17)
C22—N2—C16—C17	159.9 (2)	C17—C18—C19—C20	0.3 (3)
N1—C1—C6—C5	178.2 (2)	Cl2—C19—C20—C21	178.95 (17)
C6—C1—C2—C3	−1.9 (3)	C18—C19—C20—C21	−0.3 (3)
N1—C1—C2—C3	−178.78 (19)	C19—C20—C21—C16	0.5 (3)
C2—C1—C6—C5	1.5 (3)	N2—C22—C23—C24	1.6 (3)
C1—C2—C3—C4	1.2 (3)	N2—C22—C23—C28	−178.1 (2)
C2—C3—C4—Cl1	−179.88 (17)	C22—C23—C24—C25	179.9 (2)
C2—C3—C4—C5	−0.1 (3)	C28—C23—C24—C25	−0.4 (3)
Cl1—C4—C5—C6	179.46 (17)	C22—C23—C28—C27	179.6 (2)
C3—C4—C5—C6	−0.3 (3)	C24—C23—C28—C27	0.0 (4)
C4—C5—C6—C1	−0.4 (3)	C23—C24—C25—O3	179.9 (2)
N1—C7—C8—C9	3.9 (3)	C23—C24—C25—C26	0.2 (3)
N1—C7—C8—C13	−175.8 (2)	O3—C25—C26—O4	0.8 (3)
C7—C8—C9—C10	179.8 (2)	O3—C25—C26—C27	−179.21 (19)
C9—C8—C13—C12	−0.6 (3)	C24—C25—C26—O4	−179.42 (19)
C13—C8—C9—C10	−0.5 (3)	C24—C25—C26—C27	0.5 (3)
C7—C8—C13—C12	179.1 (2)	O4—C26—C27—C28	179.0 (2)
C8—C9—C10—C11	1.5 (3)	C25—C26—C27—C28	−1.0 (3)
C8—C9—C10—O2	−178.0 (2)	C26—C27—C28—C23	0.7 (4)

Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C8–C13 and C16–C21 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···O3i	0.96	2.52	3.468 (3)	170
C6—H6···Cg3ii	0.93	2.85	3.602 (2)	139
C18—H18···Cg1	0.93	2.89	3.588 (2)	133
C21—H21···Cg3iii	0.93	2.88	3.549 (2)	130
C29—H29C···Cg2	0.96	2.88	3.782 (2)	157
C30—H30C···Cg1iv	0.96	2.76	3.613 (2)	148

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C8–C13 and C16–C21 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14B⋯O3i	0.96	2.52	3.468 (3)	170
C6—H6⋯Cg3ii	0.93	2.85	3.602 (2)	139
C18—H18⋯Cg1	0.93	2.89	3.588 (2)	133
C21—H21⋯Cg3iii	0.93	2.88	3.549 (2)	130
C29—H29C⋯Cg2	0.96	2.88	3.782 (2)	157
C30—H30C⋯Cg1iv	0.96	2.76	3.613 (2)	148

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