Crystal structure of 2-[(3S,4S)-4-(anthracen-9-yl)-1-(4-meth-oxy-phen-yl)-2-oxoazetidin-3-yl]-2-aza-2H-phenalene-1,3-dione unknown solvate.

The central β-lactam ring of the title compound, C36H24N2O4, is almost planar (r.m.s. deviation = 0.003 Å) and makes dihedral angles of 17.17 (19), 89.76 (17) and 78.44 (17)° with the benzene ring, the anthracene ring (r.m.s. deviation = 0.003 Å) and the 1H-benzo[de]iso-quinoline-1,3(2H)-dione moiety, which is nearly planar [maximum deviation = 0.098 (2) Å], respectively. The mol-ecular structure is stabilized by an intra-molecular C-H⋯N hydrogen bond. In the crystal, mol-ecules are linked via C-H⋯π and π-π stacking inter-actions [centroid-centroid distances = 3.5270 (19) and 3.779 (2) Å], forming a three-dimensional structure. A region of disordered electron density, probably disordered solvent mol-ecules, was treated with the SQUEEZE procedure in PLATON [Spek (2015 ▶). Acta Cryst. C71, 9-18], which indicated a solvent cavity of 322 Å(3) containing approximately 91 electrons. Their formula mass and unit-cell characteristics were not taken into account during the refinement.

Related literature

For general background to β-lactams and their biological properties, see: Fischbach & Walsh (2009 ▸); Georg (1992 ▸); Kim et al. (2014 ▸); Ocampo & Dolbier (2004 ▸); Palomo et al. (2004 ▸); Smith et al. (2014 ▸); Soengas et al. (2011 ▸); von Nussbaum et al. (2006 ▸); Walsh & Wencewicz (2014 ▸). For related structures, see: Çelik et al. (2015 ▸); Atioğlu et al. (2014 ▸); Butcher et al. (2011 ▸); Jarrahpour et al. (2012 ▸); Jarrahpoor & Khalili (2007 ▸); Jarrahpour & Ebrahimi (2010 ▸). For details of the SQUEEZE procedure in PLATON, see: Spek (2015 ▸).

Experimental

Crystal data

C36H24N2O4

M = 548.57

Monoclinic,

a = 9.9880 (1) Å

b = 29.1281 (4) Å

c = 11.0751 (2) Å

β = 101.367 (1)°

V = 3158.89 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.35 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

33697 measured reflections

6431 independent reflections

3502 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.072

wR(F 2) = 0.242

S = 1.10

6431 reflections

349 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.39 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: SHELXS2014 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: SHELXL2014 and PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015002959/su5084sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015002959/su5084Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015002959/su5084Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015002959/su5084fig1.tif

Perspective view of the mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Click here for additional data file.

a . DOI: 10.1107/S2056989015002959/su5084fig2.tif

View along a-axis of the crystal packing of the title compound.

CCDC reference: 1048898

Additional supporting information: crystallographic information; 3D view; checkCIF report

C36H24N2O4	F(000) = 1144
Mr = 548.57	Dx = 1.153 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4703 reflections
a = 9.9880 (1) Å	θ = 2.5–21.8°
b = 29.1281 (4) Å	µ = 0.08 mm−1
c = 11.0751 (2) Å	T = 296 K
β = 101.367 (1)°	Prism, yellow
V = 3158.89 (8) Å3	0.35 × 0.20 × 0.15 mm
Z = 4

Bruker APEXII CCD diffractometer	3502 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.045
Graphite monochromator	θmax = 26.4°, θmin = 1.4°
φ and ω scans	h = −12→12
33697 measured reflections	k = −36→36
6431 independent reflections	l = −13→13

Refinement on F2	2 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.072	H-atom parameters constrained
wR(F2) = 0.242	w = 1/[σ2(Fo2) + (0.1309P)2] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
6431 reflections	Δρmax = 0.39 e Å−3
349 parameters	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 on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
O1	0.4190 (2)	0.35039 (7)	0.24633 (19)	0.0692 (8)
O2	0.46467 (19)	0.36965 (7)	0.52700 (19)	0.0693 (8)
O3	0.0898 (2)	0.45145 (8)	0.3595 (3)	0.1045 (10)
O4	0.4750 (3)	0.12563 (9)	0.3656 (3)	0.1069 (11)
N1	0.2807 (2)	0.30426 (7)	0.3470 (2)	0.0543 (8)
N2	0.2815 (2)	0.41138 (7)	0.4404 (2)	0.0572 (8)
C1	0.3327 (3)	0.34368 (9)	0.3064 (3)	0.0563 (9)
C2	0.2321 (3)	0.37334 (9)	0.3612 (3)	0.0554 (9)
C3	0.1920 (2)	0.32787 (9)	0.4197 (3)	0.0526 (9)
C4	0.4052 (3)	0.40621 (10)	0.5227 (3)	0.0588 (10)
C5	0.4560 (3)	0.44602 (11)	0.5995 (3)	0.0728 (6)
C6	0.5807 (3)	0.44420 (11)	0.6764 (3)	0.0728 (6)
C7	0.6296 (4)	0.48285 (15)	0.7508 (4)	0.0961 (17)
C8	0.5545 (5)	0.52161 (15)	0.7453 (4)	0.0965 (17)
C9	0.4259 (4)	0.52484 (12)	0.6675 (3)	0.0839 (14)
C10	0.3769 (3)	0.48620 (11)	0.5934 (3)	0.0728 (6)
C11	0.2496 (3)	0.48927 (11)	0.5132 (3)	0.0728 (6)
C12	0.1705 (4)	0.52855 (12)	0.5103 (5)	0.1133 (13)
C13	0.2184 (4)	0.56608 (13)	0.5837 (5)	0.1133 (13)
C14	0.3441 (5)	0.56448 (13)	0.6599 (4)	0.1056 (18)
C15	0.1979 (3)	0.45068 (10)	0.4311 (3)	0.0724 (13)
C16	0.0415 (2)	0.31708 (8)	0.4028 (2)	0.0495 (9)
C17	−0.0176 (3)	0.31832 (10)	0.5074 (3)	0.0564 (9)
C18	0.0568 (3)	0.32229 (14)	0.6311 (3)	0.0874 (13)
C19	−0.0069 (4)	0.3238 (2)	0.7281 (4)	0.1318 (16)
C20	−0.1489 (4)	0.3223 (2)	0.7123 (4)	0.1318 (16)
C21	−0.2248 (3)	0.31779 (16)	0.5989 (4)	0.0983 (18)
C22	−0.1647 (3)	0.31528 (10)	0.4932 (3)	0.0639 (11)
C23	−0.2446 (3)	0.31168 (10)	0.3770 (3)	0.0657 (11)
C24	−0.1887 (3)	0.30945 (10)	0.2726 (3)	0.0591 (10)
C25	−0.2736 (3)	0.30603 (14)	0.1548 (3)	0.0866 (13)
C26	−0.2207 (4)	0.30221 (16)	0.0529 (4)	0.1054 (18)
C27	−0.0786 (4)	0.30242 (15)	0.0617 (3)	0.0986 (16)
C28	0.0072 (3)	0.30741 (13)	0.1722 (3)	0.0786 (13)
C29	−0.0427 (3)	0.31138 (9)	0.2845 (3)	0.0562 (10)
C30	0.3253 (2)	0.25829 (9)	0.3516 (2)	0.0479 (8)
C31	0.2942 (3)	0.22912 (10)	0.4384 (3)	0.0611 (10)
C32	0.3417 (3)	0.18386 (11)	0.4453 (3)	0.0708 (11)
C33	0.4222 (3)	0.16891 (11)	0.3658 (3)	0.0694 (11)
C34	0.4512 (3)	0.19801 (11)	0.2776 (3)	0.0669 (11)
C35	0.4034 (3)	0.24258 (10)	0.2700 (3)	0.0589 (10)
C36	0.4632 (7)	0.09623 (15)	0.4623 (5)	0.140 (3)
H2	0.15700	0.38340	0.29570	0.0660*
H3	0.23420	0.32690	0.50740	0.0630*
H6	0.63360	0.41780	0.68020	0.0870*
H7	0.71420	0.48140	0.80390	0.1150*
H8	0.58870	0.54660	0.79400	0.1160*
H12	0.08480	0.52980	0.45890	0.1360*
H13	0.16490	0.59230	0.58100	0.1360*
H14	0.37590	0.59000	0.70750	0.1270*
H18	0.15160	0.32390	0.64540	0.1050*
H19	0.04530	0.32580	0.80730	0.1580*
H20	−0.19060	0.32450	0.78010	0.1580*
H21	−0.31930	0.31630	0.58930	0.1180*
H23	−0.33910	0.31070	0.36870	0.0790*
H25	−0.36790	0.30640	0.14770	0.1040*
H26	−0.27820	0.29940	−0.02370	0.1270*
H27	−0.04280	0.29910	−0.00920	0.1180*
H28	0.10090	0.30830	0.17520	0.0940*
H31	0.24110	0.23940	0.49320	0.0730*
H32	0.31880	0.16390	0.50360	0.0850*
H34	0.50360	0.18770	0.22240	0.0800*
H35	0.42380	0.26210	0.20970	0.0710*
H36A	0.50430	0.06720	0.45060	0.2110*
H36B	0.50860	0.10950	0.53880	0.2110*
H36C	0.36840	0.09170	0.46410	0.2110*

	U11	U22	U33	U12	U13	U23
O1	0.0567 (11)	0.0759 (14)	0.0813 (14)	−0.0105 (10)	0.0287 (11)	0.0031 (11)
O2	0.0529 (11)	0.0635 (13)	0.0879 (15)	0.0010 (9)	0.0048 (10)	0.0021 (10)
O3	0.0591 (14)	0.0813 (16)	0.162 (2)	0.0163 (12)	−0.0051 (16)	−0.0168 (16)
O4	0.146 (2)	0.0762 (16)	0.1096 (19)	0.0450 (15)	0.0521 (18)	0.0099 (15)
N1	0.0392 (11)	0.0551 (14)	0.0709 (15)	0.0010 (9)	0.0166 (11)	0.0024 (11)
N2	0.0437 (12)	0.0479 (13)	0.0800 (16)	−0.0018 (9)	0.0120 (11)	−0.0019 (11)
C1	0.0409 (14)	0.0601 (17)	0.0673 (18)	−0.0064 (12)	0.0093 (13)	0.0001 (14)
C2	0.0407 (13)	0.0516 (15)	0.0742 (18)	0.0021 (11)	0.0121 (13)	0.0030 (13)
C3	0.0440 (14)	0.0528 (15)	0.0634 (17)	0.0015 (11)	0.0162 (13)	−0.0020 (12)
C4	0.0447 (15)	0.0578 (18)	0.0767 (19)	−0.0046 (13)	0.0185 (14)	0.0030 (14)
C5	0.0643 (9)	0.0668 (10)	0.0908 (12)	−0.0112 (8)	0.0237 (8)	−0.0039 (9)
C6	0.0643 (9)	0.0668 (10)	0.0908 (12)	−0.0112 (8)	0.0237 (8)	−0.0039 (9)
C7	0.092 (3)	0.105 (3)	0.086 (3)	−0.034 (2)	0.005 (2)	−0.002 (2)
C8	0.109 (3)	0.090 (3)	0.096 (3)	−0.035 (2)	0.034 (3)	−0.020 (2)
C9	0.083 (2)	0.078 (2)	0.099 (3)	−0.0250 (19)	0.038 (2)	−0.0199 (19)
C10	0.0643 (9)	0.0668 (10)	0.0908 (12)	−0.0112 (8)	0.0237 (8)	−0.0039 (9)
C11	0.0643 (9)	0.0668 (10)	0.0908 (12)	−0.0112 (8)	0.0237 (8)	−0.0039 (9)
C12	0.0867 (19)	0.0623 (16)	0.197 (3)	0.0013 (14)	0.043 (2)	−0.0180 (18)
C13	0.0867 (19)	0.0623 (16)	0.197 (3)	0.0013 (14)	0.043 (2)	−0.0180 (18)
C14	0.114 (3)	0.066 (2)	0.153 (4)	−0.019 (2)	0.066 (3)	−0.032 (2)
C15	0.0497 (17)	0.0564 (18)	0.112 (3)	−0.0007 (13)	0.0181 (18)	−0.0051 (17)
C16	0.0392 (13)	0.0479 (14)	0.0624 (17)	0.0054 (10)	0.0124 (13)	0.0035 (12)
C17	0.0415 (14)	0.0648 (17)	0.0644 (18)	0.0123 (12)	0.0138 (13)	0.0084 (13)
C18	0.0500 (17)	0.143 (3)	0.070 (2)	0.0187 (19)	0.0141 (17)	0.006 (2)
C19	0.0717 (16)	0.255 (4)	0.0734 (18)	0.042 (2)	0.0260 (16)	0.025 (2)
C20	0.0717 (16)	0.255 (4)	0.0734 (18)	0.042 (2)	0.0260 (16)	0.025 (2)
C21	0.0488 (18)	0.162 (4)	0.092 (3)	0.023 (2)	0.0334 (19)	0.029 (2)
C22	0.0419 (15)	0.080 (2)	0.073 (2)	0.0101 (13)	0.0193 (15)	0.0148 (15)
C23	0.0366 (14)	0.077 (2)	0.085 (2)	0.0002 (13)	0.0157 (15)	0.0066 (16)
C24	0.0407 (14)	0.0654 (17)	0.0695 (19)	−0.0064 (12)	0.0071 (14)	0.0018 (14)
C25	0.0479 (17)	0.125 (3)	0.084 (2)	−0.0092 (18)	0.0056 (18)	−0.001 (2)
C26	0.069 (2)	0.163 (4)	0.076 (3)	−0.009 (2)	−0.006 (2)	−0.007 (2)
C27	0.074 (2)	0.156 (4)	0.064 (2)	−0.003 (2)	0.0090 (19)	−0.013 (2)
C28	0.0540 (18)	0.110 (3)	0.073 (2)	0.0051 (17)	0.0155 (17)	−0.0026 (18)
C29	0.0432 (14)	0.0580 (16)	0.0682 (19)	−0.0004 (12)	0.0133 (14)	0.0002 (13)
C30	0.0343 (12)	0.0510 (15)	0.0572 (15)	−0.0027 (10)	0.0062 (11)	−0.0019 (12)
C31	0.0573 (16)	0.0622 (18)	0.0669 (18)	0.0035 (13)	0.0201 (14)	−0.0074 (14)
C32	0.083 (2)	0.0640 (19)	0.068 (2)	0.0059 (16)	0.0216 (17)	0.0058 (15)
C33	0.078 (2)	0.0605 (19)	0.070 (2)	0.0130 (15)	0.0157 (17)	−0.0077 (16)
C34	0.0632 (18)	0.073 (2)	0.069 (2)	0.0064 (15)	0.0242 (15)	−0.0094 (16)
C35	0.0480 (15)	0.0676 (19)	0.0627 (17)	0.0014 (13)	0.0146 (13)	−0.0012 (14)
C36	0.208 (6)	0.084 (3)	0.144 (4)	0.060 (3)	0.071 (4)	0.033 (3)

O1—C1	1.204 (4)	C24—C25	1.412 (5)
O2—C4	1.216 (4)	C24—C29	1.439 (4)
O3—C15	1.207 (4)	C25—C26	1.342 (5)
O4—C33	1.367 (4)	C26—C27	1.403 (6)
O4—C36	1.394 (6)	C27—C28	1.356 (5)
N1—C1	1.372 (3)	C28—C29	1.433 (5)
N1—C3	1.479 (3)	C30—C31	1.364 (4)
N1—C30	1.409 (3)	C30—C35	1.383 (4)
N2—C2	1.439 (4)	C31—C32	1.398 (4)
N2—C4	1.391 (4)	C32—C33	1.375 (4)
N2—C15	1.409 (4)	C33—C34	1.367 (5)
C1—C2	1.538 (4)	C34—C35	1.380 (4)
C2—C3	1.561 (4)	C2—H2	0.9800
C3—C16	1.511 (3)	C3—H3	0.9800
C4—C5	1.468 (4)	C6—H6	0.9300
C5—C6	1.364 (4)	C7—H7	0.9300
C5—C10	1.406 (4)	C8—H8	0.9300
C6—C7	1.424 (5)	C12—H12	0.9300
C7—C8	1.350 (6)	C13—H13	0.9300
C8—C9	1.402 (6)	C14—H14	0.9300
C9—C10	1.422 (5)	C18—H18	0.9300
C9—C14	1.407 (6)	C19—H19	0.9300
C10—C11	1.403 (4)	C20—H20	0.9300
C11—C12	1.387 (5)	C21—H21	0.9300
C11—C15	1.474 (4)	C23—H23	0.9300
C12—C13	1.390 (6)	C25—H25	0.9300
C13—C14	1.369 (7)	C26—H26	0.9300
C16—C17	1.401 (4)	C27—H27	0.9300
C16—C29	1.420 (4)	C28—H28	0.9300
C17—C18	1.429 (5)	C31—H31	0.9300
C17—C22	1.449 (4)	C32—H32	0.9300
C18—C19	1.353 (5)	C34—H34	0.9300
C19—C20	1.395 (6)	C35—H35	0.9300
C20—C21	1.339 (6)	C36—H36A	0.9600
C21—C22	1.419 (5)	C36—H36B	0.9600
C22—C23	1.378 (5)	C36—H36C	0.9600
C23—C24	1.381 (5)
C33—O4—C36	118.3 (3)	C16—C29—C28	124.5 (3)
C1—N1—C3	95.5 (2)	C24—C29—C28	115.9 (3)
C1—N1—C30	132.1 (2)	N1—C30—C31	120.2 (2)
C3—N1—C30	129.9 (2)	N1—C30—C35	120.4 (2)
C2—N2—C4	118.0 (2)	C31—C30—C35	119.4 (3)
C2—N2—C15	117.0 (2)	C30—C31—C32	120.3 (3)
C4—N2—C15	125.0 (2)	C31—C32—C33	119.9 (3)
O1—C1—N1	132.5 (3)	O4—C33—C32	124.6 (3)
O1—C1—C2	136.2 (3)	O4—C33—C34	115.8 (3)
N1—C1—C2	91.3 (2)	C32—C33—C34	119.6 (3)
N2—C2—C1	120.1 (2)	C33—C34—C35	120.5 (3)
N2—C2—C3	119.1 (3)	C30—C35—C34	120.3 (3)
C1—C2—C3	85.88 (19)	N2—C2—H2	110.00
N1—C3—C2	86.47 (19)	C1—C2—H2	110.00
N1—C3—C16	121.6 (2)	C3—C2—H2	110.00
C2—C3—C16	117.1 (2)	N1—C3—H3	110.00
O2—C4—N2	119.0 (3)	C2—C3—H3	110.00
O2—C4—C5	124.0 (3)	C16—C3—H3	110.00
N2—C4—C5	117.1 (3)	C5—C6—H6	120.00
C4—C5—C6	120.0 (3)	C7—C6—H6	120.00
C4—C5—C10	120.2 (3)	C6—C7—H7	120.00
C6—C5—C10	119.8 (3)	C8—C7—H7	120.00
C5—C6—C7	119.8 (3)	C7—C8—H8	119.00
C6—C7—C8	120.7 (4)	C9—C8—H8	119.00
C7—C8—C9	121.2 (4)	C11—C12—H12	120.00
C8—C9—C10	118.1 (3)	C13—C12—H12	120.00
C8—C9—C14	122.9 (4)	C12—C13—H13	120.00
C10—C9—C14	119.0 (3)	C14—C13—H13	120.00
C5—C10—C9	120.3 (3)	C9—C14—H14	119.00
C5—C10—C11	120.9 (3)	C13—C14—H14	119.00
C9—C10—C11	118.7 (3)	C17—C18—H18	119.00
C10—C11—C12	120.5 (3)	C19—C18—H18	119.00
C10—C11—C15	120.4 (3)	C18—C19—H19	119.00
C12—C11—C15	119.1 (3)	C20—C19—H19	119.00
C11—C12—C13	120.4 (4)	C19—C20—H20	120.00
C12—C13—C14	120.1 (4)	C21—C20—H20	120.00
C9—C14—C13	121.1 (4)	C20—C21—H21	119.00
O3—C15—N2	120.2 (3)	C22—C21—H21	119.00
O3—C15—C11	123.4 (3)	C22—C23—H23	119.00
N2—C15—C11	116.4 (3)	C24—C23—H23	119.00
C3—C16—C17	117.6 (2)	C24—C25—H25	119.00
C3—C16—C29	122.2 (2)	C26—C25—H25	119.00
C17—C16—C29	119.8 (2)	C25—C26—H26	120.00
C16—C17—C18	124.8 (3)	C27—C26—H26	120.00
C16—C17—C22	119.5 (3)	C26—C27—H27	120.00
C18—C17—C22	115.7 (3)	C28—C27—H27	120.00
C17—C18—C19	121.8 (3)	C27—C28—H28	119.00
C18—C19—C20	121.7 (4)	C29—C28—H28	119.00
C19—C20—C21	119.6 (4)	C30—C31—H31	120.00
C20—C21—C22	121.7 (3)	C32—C31—H31	120.00
C17—C22—C21	119.5 (3)	C31—C32—H32	120.00
C17—C22—C23	119.6 (3)	C33—C32—H32	120.00
C21—C22—C23	120.9 (3)	C33—C34—H34	120.00
C22—C23—C24	122.0 (3)	C35—C34—H34	120.00
C23—C24—C25	120.6 (3)	C30—C35—H35	120.00
C23—C24—C29	119.4 (3)	C34—C35—H35	120.00
C25—C24—C29	120.0 (3)	O4—C36—H36A	110.00
C24—C25—C26	121.2 (3)	O4—C36—H36B	110.00
C25—C26—C27	120.1 (4)	O4—C36—H36C	109.00
C26—C27—C28	120.9 (3)	H36A—C36—H36B	109.00
C27—C28—C29	121.7 (3)	H36A—C36—H36C	109.00
C16—C29—C24	119.6 (3)	H36B—C36—H36C	109.00
C36—O4—C33—C32	−9.3 (6)	C10—C9—C14—C13	0.7 (6)
C36—O4—C33—C34	172.3 (4)	C9—C10—C11—C15	177.4 (3)
C3—N1—C1—C2	−7.7 (2)	C5—C10—C11—C15	−1.6 (5)
C30—N1—C1—C2	−170.2 (3)	C9—C10—C11—C12	−2.8 (5)
C1—N1—C30—C31	152.4 (3)	C5—C10—C11—C12	178.2 (3)
C3—N1—C30—C31	−4.7 (4)	C15—C11—C12—C13	−177.9 (4)
C1—N1—C30—C35	−26.2 (4)	C12—C11—C15—O3	0.8 (5)
C3—N1—C30—C35	176.7 (3)	C10—C11—C12—C13	2.3 (6)
C3—N1—C1—O1	175.5 (4)	C12—C11—C15—N2	−178.6 (3)
C30—N1—C1—O1	12.9 (6)	C10—C11—C15—O3	−179.4 (3)
C30—N1—C3—C2	170.7 (2)	C10—C11—C15—N2	1.2 (4)
C1—N1—C3—C16	127.4 (3)	C11—C12—C13—C14	−0.2 (7)
C30—N1—C3—C16	−69.4 (4)	C12—C13—C14—C9	−1.3 (7)
C1—N1—C3—C2	7.6 (2)	C29—C16—C17—C18	177.7 (3)
C15—N2—C2—C1	144.1 (3)	C3—C16—C17—C22	170.5 (2)
C2—N2—C15—O3	0.3 (4)	C3—C16—C17—C18	−9.8 (4)
C15—N2—C4—C5	−4.3 (4)	C29—C16—C17—C22	−2.0 (4)
C4—N2—C2—C3	65.2 (3)	C3—C16—C29—C24	−168.8 (2)
C4—N2—C2—C1	−38.0 (4)	C17—C16—C29—C28	−176.8 (3)
C15—N2—C2—C3	−112.9 (3)	C17—C16—C29—C24	3.4 (4)
C4—N2—C15—O3	−177.5 (3)	C3—C16—C29—C28	11.0 (4)
C2—N2—C4—O2	−2.0 (4)	C16—C17—C22—C21	−178.3 (3)
C2—N2—C15—C11	179.7 (3)	C16—C17—C22—C23	−0.7 (4)
C2—N2—C4—C5	177.9 (3)	C18—C17—C22—C21	1.9 (5)
C4—N2—C15—C11	1.9 (4)	C18—C17—C22—C23	179.6 (3)
C15—N2—C4—O2	175.9 (3)	C22—C17—C18—C19	−1.0 (6)
O1—C1—C2—N2	−54.7 (5)	C16—C17—C18—C19	179.3 (4)
O1—C1—C2—C3	−176.1 (4)	C17—C18—C19—C20	−1.1 (8)
N1—C1—C2—N2	128.6 (3)	C18—C19—C20—C21	2.2 (9)
N1—C1—C2—C3	7.3 (2)	C19—C20—C21—C22	−1.1 (8)
N2—C2—C3—C16	107.0 (3)	C20—C21—C22—C23	−178.5 (4)
C1—C2—C3—N1	−6.7 (2)	C20—C21—C22—C17	−0.9 (6)
N2—C2—C3—N1	−129.1 (3)	C21—C22—C23—C24	179.6 (3)
C1—C2—C3—C16	−130.7 (3)	C17—C22—C23—C24	2.0 (4)
N1—C3—C16—C17	144.6 (3)	C22—C23—C24—C25	−179.6 (3)
C2—C3—C16—C17	−111.9 (3)	C22—C23—C24—C29	−0.6 (4)
C2—C3—C16—C29	60.4 (3)	C23—C24—C29—C16	−2.1 (4)
N1—C3—C16—C29	−43.1 (4)	C23—C24—C29—C28	178.1 (3)
N2—C4—C5—C10	3.7 (4)	C29—C24—C25—C26	3.4 (6)
O2—C4—C5—C6	4.0 (5)	C25—C24—C29—C28	−2.9 (4)
N2—C4—C5—C6	−175.8 (3)	C25—C24—C29—C16	176.9 (3)
O2—C4—C5—C10	−176.5 (3)	C23—C24—C25—C26	−177.6 (4)
C4—C5—C10—C9	−179.9 (3)	C24—C25—C26—C27	−1.2 (7)
C6—C5—C10—C11	178.7 (3)	C25—C26—C27—C28	−1.4 (7)
C10—C5—C6—C7	0.5 (5)	C26—C27—C28—C29	1.8 (6)
C4—C5—C6—C7	−180.0 (3)	C27—C28—C29—C24	0.4 (5)
C4—C5—C10—C11	−0.9 (5)	C27—C28—C29—C16	−179.4 (3)
C6—C5—C10—C9	−0.4 (5)	N1—C30—C35—C34	177.6 (3)
C5—C6—C7—C8	−0.7 (6)	C31—C30—C35—C34	−1.0 (4)
C6—C7—C8—C9	0.7 (7)	N1—C30—C31—C32	−178.2 (3)
C7—C8—C9—C10	−0.5 (6)	C35—C30—C31—C32	0.5 (4)
C7—C8—C9—C14	179.5 (4)	C30—C31—C32—C33	1.2 (5)
C8—C9—C10—C5	0.4 (5)	C31—C32—C33—C34	−2.3 (5)
C14—C9—C10—C5	−179.7 (3)	C31—C32—C33—O4	179.3 (3)
C14—C9—C10—C11	1.3 (5)	O4—C33—C34—C35	−179.7 (3)
C8—C9—C10—C11	−178.7 (3)	C32—C33—C34—C35	1.8 (5)
C8—C9—C14—C13	−179.3 (4)	C33—C34—C35—C30	−0.1 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28···N1	0.93	2.35	3.022 (4)	129
C13—H13···Cg5i	0.93	2.84	3.713 (4)	158

Table 1

Hydrogen-bond geometry (, )

Cg5 is the centroid of the C16/C17/C22C24/C29 benzene ring.

DHA	DH	HA	D A	DHA
C28H28N1	0.93	2.35	3.022(4)	129
C13H13Cg5i	0.93	2.84	3.713(4)	158

Symmetry code: (i) .