Crystal structure of 2-[4-(4-chloro-phen-yl)-1-(4-meth-oxy-phen-yl)-2-oxoazetidin-3-yl]benzo[de]iso-quinoline-1,3-dione dimethyl sulfoxide monosolvate.

In the title solvated compound, C28H19N2O4·C2H6OS, the central β-lactam ring is almost planar (r.m.s. deviation = 0.002 Å). It makes dihedral angles of 1.92 (11), 83.23 (12) and 74.90 (10)° with the meth-oxy- and chloro-phenyl rings and the ring plane of the 1H-benzo[de]iso-quinoline-1,3(2H)-dione group [maximum deviation = 0.089 (1)], respectively. An intra-molecular C-H⋯O hydrogen bond closes an S(6) ring and helps to establish the near coplanarity of the β-lactam and meth-oxy-benzene rings. In the crystal, the components are linked by C-H⋯O hydrogen bonds, C-H⋯π inter-actions and aromatic π-π stacking inter-actions [centroid-to-centroid distances = 3.6166 (10) and 3.7159 (10) Å], resulting in a three-dimensional network, The dimethyl sulfoxide solvent mol-ecule is disordered over two sets of sites in a 0.847 (2):0.153 (2) ratio.

Related literature

For general background to β-lactams, see: Alcaide & Almendros (2004 ▸); Alcala et al. (2011 ▸); Li et al. (2011 ▸); Long & Turos (2002 ▸); MacIntyre et al. (2010 ▸); Rogers & Kelly (1999 ▸); Sawa et al. (2006 ▸); Southgate (1994 ▸); Zhang & Zhou (2011 ▸); Zhang et al. (2011 ▸). For related structures, see: Atioğlu et al. (2014 ▸); Butcher et al. (2011 ▸); Jarrahpour et al. (2012 ▸); Zarei (2013 ▸).

Experimental

Crystal data

C28H19ClN2O4·C2H6OS

M = 561.03

Triclinic,

a = 7.9925 (3) Å

b = 12.1761 (5) Å

c = 14.2313 (6) Å

α = 93.549 (2)°

β = 95.520 (2)°

γ = 101.602 (2)°

V = 1345.67 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 296 K

0.45 × 0.30 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

29975 measured reflections

7737 independent reflections

5777 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.191

S = 1.05

7737 reflections

359 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.68 e Å−3

Δρmin = −0.52 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: PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015001425/hb7354sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015001425/hb7354Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015001425/hb7354Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015001425/hb7354fig1.tif

Perspective view of the mol­ecular structure of the title compound with displacement ellipsoids for non-H atoms drawn at the 30% probability level. Only the major component of the disordered solvent mol­ecule is displayed.

Click here for additional data file.

a . DOI: 10.1107/S2056989015001425/hb7354fig2.tif

The hydrogen bonding and mol­ecular packing of the title compound along a axis. Only the major component of the disordered solvent mol­ecule is displayed.

Click here for additional data file.

c . DOI: 10.1107/S2056989015001425/hb7354fig3.tif

The hydrogen bonding and mol­ecular packing of the title compound along c axis. Only the major component of the disordered solvent mol­ecule is displayed.

CCDC reference: 1044874

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

C28H19ClN2O4·C2H6OS	Z = 2
Mr = 561.03	F(000) = 584
Triclinic, P1	Dx = 1.385 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9925 (3) Å	Cell parameters from 9923 reflections
b = 12.1761 (5) Å	θ = 2.9–29.9°
c = 14.2313 (6) Å	µ = 0.26 mm−1
α = 93.549 (2)°	T = 296 K
β = 95.520 (2)°	Prism, colourless
γ = 101.602 (2)°	0.45 × 0.30 × 0.20 mm
V = 1345.67 (9) Å3

Bruker APEXII CCD diffractometer	5777 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.022
Graphite monochromator	θmax = 30.0°, θmin = 2.2°
φ and ω scans	h = −11→11
29975 measured reflections	k = −17→17
7737 independent reflections	l = −19→19

Refinement on F2	6 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.061	H-atom parameters constrained
wR(F2) = 0.191	w = 1/[σ2(Fo2) + (0.0977P)2 + 0.5061P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
7737 reflections	Δρmax = 0.68 e Å−3
359 parameters	Δρmin = −0.52 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	Occ. (<1)
Cl1	0.69679 (12)	0.13588 (7)	0.68363 (4)	0.0886 (3)
S1A	0.83996 (15)	0.62942 (10)	0.36822 (7)	0.0884 (4)	0.847 (2)
S1B	0.7471 (8)	0.6453 (5)	0.4182 (4)	0.0884 (4)	0.153 (2)
O1	0.5935 (2)	0.15324 (13)	0.07604 (10)	0.0572 (5)
O2	−0.20212 (18)	−0.02113 (14)	0.22243 (12)	0.0620 (5)
O3	1.06205 (19)	0.37028 (13)	0.29270 (12)	0.0603 (5)
O4	0.58077 (15)	0.40773 (12)	0.11511 (10)	0.0467 (4)
N1	0.48129 (19)	0.18953 (13)	0.21909 (10)	0.0411 (4)
N2	0.82660 (17)	0.38087 (12)	0.19376 (10)	0.0355 (4)
C1	0.5863 (2)	0.27720 (14)	0.28906 (12)	0.0368 (5)
C2	0.7342 (2)	0.27719 (14)	0.22466 (12)	0.0381 (5)
C3	0.5985 (2)	0.19748 (15)	0.15453 (13)	0.0423 (5)
C4	0.3093 (2)	0.13255 (14)	0.21725 (12)	0.0372 (5)
C5	0.2294 (3)	0.05633 (17)	0.14244 (13)	0.0469 (6)
O5A	0.6596 (5)	0.5604 (2)	0.3457 (2)	0.1081 (11)	0.847 (2)
C6	0.0575 (3)	0.00331 (17)	0.14164 (14)	0.0497 (6)
C7	−0.0327 (2)	0.02482 (16)	0.21594 (14)	0.0450 (5)
C8	0.0494 (2)	0.09910 (18)	0.29171 (15)	0.0488 (6)
C9	0.2184 (2)	0.15335 (16)	0.29214 (14)	0.0450 (6)
C10	−0.2998 (3)	−0.0868 (2)	0.1422 (2)	0.0750 (9)
C11	0.6159 (2)	0.24211 (14)	0.38776 (12)	0.0365 (4)
C12	0.6490 (2)	0.13637 (15)	0.40284 (13)	0.0413 (5)
C13	0.6763 (3)	0.10452 (17)	0.49434 (14)	0.0477 (6)
C14	0.6676 (3)	0.17782 (19)	0.56949 (14)	0.0524 (6)
C15	0.6345 (4)	0.2827 (2)	0.55697 (15)	0.0612 (8)
C16	0.6094 (3)	0.31440 (17)	0.46505 (14)	0.0500 (6)
C17	1.0008 (2)	0.41714 (14)	0.22957 (12)	0.0376 (5)
C18	1.1000 (2)	0.51167 (13)	0.18560 (11)	0.0337 (4)
C19	1.2760 (2)	0.54014 (16)	0.20663 (13)	0.0428 (5)
C20	1.3723 (2)	0.62737 (18)	0.16236 (15)	0.0495 (6)
C21	1.2935 (2)	0.68586 (17)	0.09901 (13)	0.0464 (5)
C22	1.1127 (2)	0.66006 (14)	0.07639 (12)	0.0372 (5)
C23	1.01511 (19)	0.56994 (13)	0.11954 (10)	0.0316 (4)
C24	0.83533 (19)	0.53926 (13)	0.09505 (11)	0.0325 (4)
C25	0.7550 (2)	0.59720 (15)	0.03094 (12)	0.0393 (5)
C26	0.8512 (3)	0.68702 (16)	−0.01091 (13)	0.0462 (6)
C27	1.0259 (3)	0.71740 (15)	0.01086 (13)	0.0438 (5)
C28	0.7350 (2)	0.44063 (14)	0.13389 (11)	0.0341 (4)
O5B	0.688 (3)	0.6029 (15)	0.3255 (13)	0.1081 (11)	0.153 (2)
C29A	0.8342 (10)	0.7606 (7)	0.3416 (6)	0.183 (3)	0.847 (2)
C30A	0.8821 (12)	0.6486 (7)	0.4874 (7)	0.183 (3)	0.847 (2)
C29B	0.821 (6)	0.786 (2)	0.413 (4)	0.183 (3)	0.153 (2)
C30B	0.904 (5)	0.593 (4)	0.479 (5)	0.183 (3)	0.153 (2)
H1	0.54490	0.34770	0.28880	0.0440*
H2	0.81630	0.23530	0.25290	0.0460*
H5	0.29030	0.04040	0.09260	0.0560*
H6	0.00350	−0.04690	0.09060	0.0600*
H8	−0.01000	0.11250	0.34290	0.0580*
H9	0.27160	0.20410	0.34290	0.0540*
H10A	−0.41530	−0.11360	0.15630	0.1130*
H10B	−0.30120	−0.04140	0.08940	0.1130*
H10C	−0.24890	−0.14960	0.12670	0.1130*
H12	0.65280	0.08650	0.35130	0.0500*
H13	0.70030	0.03420	0.50420	0.0570*
H15	0.62890	0.33170	0.60890	0.0730*
H16	0.58800	0.38550	0.45580	0.0600*
H19	1.33080	0.50150	0.25020	0.0510*
H20	1.49120	0.64560	0.17630	0.0590*
H21	1.35960	0.74340	0.07030	0.0560*
H25	0.63660	0.57680	0.01530	0.0470*
H26	0.79580	0.72620	−0.05380	0.0550*
H27	1.08800	0.77660	−0.01790	0.0530*
H29A	0.94730	0.80710	0.35510	0.2740*	0.847 (2)
H29B	0.79540	0.76000	0.27560	0.2740*	0.847 (2)
H29C	0.75680	0.78990	0.37900	0.2740*	0.847 (2)
H30A	0.99640	0.69240	0.50420	0.2740*	0.847 (2)
H30B	0.80100	0.68750	0.51270	0.2740*	0.847 (2)
H30C	0.87290	0.57690	0.51320	0.2740*	0.847 (2)
H29D	0.86430	0.82040	0.47590	0.2740*	0.153 (2)
H29E	0.91190	0.79800	0.37310	0.2740*	0.153 (2)
H29F	0.72910	0.81960	0.38830	0.2740*	0.153 (2)
H30D	0.93010	0.63100	0.54170	0.2740*	0.153 (2)
H30E	0.86390	0.51410	0.48360	0.2740*	0.153 (2)
H30F	1.00470	0.60530	0.44680	0.2740*	0.153 (2)

	U11	U22	U33	U12	U13	U23
Cl1	0.1404 (7)	0.0971 (5)	0.0389 (3)	0.0438 (5)	0.0117 (3)	0.0232 (3)
S1A	0.0995 (7)	0.1062 (7)	0.0621 (5)	0.0320 (6)	0.0056 (4)	−0.0015 (5)
S1B	0.0995 (7)	0.1062 (7)	0.0621 (5)	0.0320 (6)	0.0056 (4)	−0.0015 (5)
O1	0.0713 (10)	0.0540 (8)	0.0402 (7)	−0.0060 (7)	0.0177 (7)	0.0018 (6)
O2	0.0407 (7)	0.0676 (10)	0.0676 (10)	−0.0074 (7)	0.0065 (7)	−0.0120 (8)
O3	0.0527 (8)	0.0609 (9)	0.0618 (9)	0.0030 (7)	−0.0159 (7)	0.0261 (7)
O4	0.0309 (6)	0.0547 (8)	0.0505 (7)	−0.0006 (5)	−0.0019 (5)	0.0152 (6)
N1	0.0403 (7)	0.0450 (8)	0.0327 (7)	−0.0041 (6)	0.0042 (5)	0.0040 (6)
N2	0.0317 (6)	0.0381 (7)	0.0354 (7)	0.0019 (5)	0.0032 (5)	0.0111 (5)
C1	0.0355 (8)	0.0394 (8)	0.0328 (8)	0.0009 (6)	0.0036 (6)	0.0058 (6)
C2	0.0381 (8)	0.0385 (8)	0.0369 (8)	0.0030 (6)	0.0065 (6)	0.0104 (6)
C3	0.0478 (9)	0.0399 (8)	0.0368 (9)	0.0002 (7)	0.0085 (7)	0.0083 (7)
C4	0.0378 (8)	0.0368 (8)	0.0353 (8)	0.0027 (6)	0.0020 (6)	0.0091 (6)
C5	0.0503 (10)	0.0490 (10)	0.0361 (9)	−0.0030 (8)	0.0077 (7)	0.0025 (7)
O5A	0.128 (2)	0.0609 (17)	0.112 (2)	−0.0059 (18)	−0.0486 (19)	0.0060 (15)
C6	0.0515 (10)	0.0459 (10)	0.0431 (10)	−0.0064 (8)	0.0025 (8)	−0.0035 (8)
C7	0.0393 (9)	0.0410 (9)	0.0508 (10)	0.0012 (7)	0.0023 (7)	0.0009 (7)
C8	0.0377 (9)	0.0554 (11)	0.0507 (11)	0.0063 (8)	0.0067 (7)	−0.0065 (8)
C9	0.0383 (9)	0.0486 (10)	0.0440 (10)	0.0051 (7)	−0.0001 (7)	−0.0077 (8)
C10	0.0529 (13)	0.0739 (16)	0.0820 (18)	−0.0143 (11)	0.0018 (12)	−0.0205 (13)
C11	0.0332 (7)	0.0404 (8)	0.0335 (8)	0.0008 (6)	0.0045 (6)	0.0061 (6)
C12	0.0458 (9)	0.0401 (8)	0.0376 (9)	0.0059 (7)	0.0084 (7)	0.0044 (7)
C13	0.0555 (11)	0.0449 (9)	0.0448 (10)	0.0109 (8)	0.0092 (8)	0.0122 (8)
C14	0.0626 (12)	0.0604 (12)	0.0352 (9)	0.0123 (9)	0.0059 (8)	0.0120 (8)
C15	0.0901 (17)	0.0599 (13)	0.0355 (10)	0.0227 (12)	0.0047 (10)	−0.0008 (9)
C16	0.0686 (13)	0.0423 (9)	0.0395 (10)	0.0142 (9)	0.0025 (8)	0.0031 (7)
C17	0.0347 (8)	0.0404 (8)	0.0358 (8)	0.0052 (6)	−0.0021 (6)	0.0056 (6)
C18	0.0310 (7)	0.0361 (7)	0.0313 (7)	0.0025 (6)	0.0011 (5)	−0.0008 (6)
C19	0.0334 (8)	0.0491 (9)	0.0418 (9)	0.0044 (7)	−0.0029 (6)	−0.0031 (7)
C20	0.0315 (8)	0.0594 (11)	0.0495 (10)	−0.0059 (7)	0.0027 (7)	−0.0061 (8)
C21	0.0417 (9)	0.0475 (9)	0.0417 (9)	−0.0108 (7)	0.0095 (7)	−0.0029 (7)
C22	0.0416 (8)	0.0344 (8)	0.0316 (8)	−0.0019 (6)	0.0076 (6)	−0.0016 (6)
C23	0.0324 (7)	0.0323 (7)	0.0276 (7)	0.0017 (5)	0.0037 (5)	−0.0009 (5)
C24	0.0326 (7)	0.0341 (7)	0.0296 (7)	0.0037 (6)	0.0029 (5)	0.0039 (6)
C25	0.0399 (8)	0.0411 (8)	0.0361 (8)	0.0083 (7)	−0.0003 (6)	0.0057 (7)
C26	0.0590 (11)	0.0409 (9)	0.0401 (9)	0.0130 (8)	0.0031 (8)	0.0106 (7)
C27	0.0561 (10)	0.0345 (8)	0.0382 (9)	−0.0002 (7)	0.0105 (7)	0.0060 (7)
C28	0.0310 (7)	0.0389 (8)	0.0312 (7)	0.0040 (6)	0.0020 (5)	0.0069 (6)
O5B	0.128 (2)	0.0609 (17)	0.112 (2)	−0.0059 (18)	−0.0486 (19)	0.0060 (15)
C29A	0.140 (4)	0.184 (6)	0.187 (5)	−0.034 (4)	−0.060 (4)	0.058 (5)
C30A	0.140 (4)	0.184 (6)	0.187 (5)	−0.034 (4)	−0.060 (4)	0.058 (5)
C29B	0.140 (4)	0.184 (6)	0.187 (5)	−0.034 (4)	−0.060 (4)	0.058 (5)
C30B	0.140 (4)	0.184 (6)	0.187 (5)	−0.034 (4)	−0.060 (4)	0.058 (5)

Cl1—C14	1.741 (2)	C22—C23	1.422 (2)
S1A—C30A	1.689 (10)	C22—C27	1.411 (3)
S1A—O5A	1.509 (4)	C23—C24	1.413 (2)
S1A—C29A	1.673 (8)	C24—C25	1.375 (2)
S1B—O5B	1.388 (19)	C24—C28	1.473 (2)
S1B—C30B	1.71 (5)	C25—C26	1.405 (3)
S1B—C29B	1.71 (3)	C26—C27	1.370 (3)
O1—C3	1.203 (2)	C1—H1	0.9800
O2—C10	1.420 (3)	C2—H2	0.9800
O2—C7	1.371 (2)	C5—H5	0.9300
O3—C17	1.210 (2)	C6—H6	0.9300
O4—C28	1.215 (2)	C8—H8	0.9300
N1—C3	1.368 (2)	C9—H9	0.9300
N1—C1	1.477 (2)	C10—H10C	0.9600
N1—C4	1.407 (2)	C10—H10B	0.9600
N2—C28	1.401 (2)	C10—H10A	0.9600
N2—C2	1.445 (2)	C12—H12	0.9300
N2—C17	1.408 (2)	C13—H13	0.9300
C1—C2	1.564 (2)	C15—H15	0.9300
C1—C11	1.504 (2)	C16—H16	0.9300
C2—C3	1.537 (2)	C19—H19	0.9300
C4—C5	1.382 (3)	C20—H20	0.9300
C4—C9	1.385 (2)	C21—H21	0.9300
C5—C6	1.394 (3)	C25—H25	0.9300
C6—C7	1.377 (3)	C26—H26	0.9300
C7—C8	1.384 (3)	C27—H27	0.9300
C8—C9	1.378 (2)	C29A—H29C	0.9600
C11—C12	1.391 (2)	C29A—H29A	0.9600
C11—C16	1.377 (3)	C29A—H29B	0.9600
C12—C13	1.391 (3)	C30A—H30A	0.9600
C13—C14	1.366 (3)	C30A—H30B	0.9600
C14—C15	1.374 (3)	C30A—H30C	0.9600
C15—C16	1.394 (3)	C29B—H29D	0.9700
C17—C18	1.471 (2)	C29B—H29E	0.9600
C18—C23	1.415 (2)	C29B—H29F	0.9600
C18—C19	1.378 (2)	C30B—H30D	0.9600
C19—C20	1.402 (3)	C30B—H30E	0.9600
C20—C21	1.367 (3)	C30B—H30F	0.9500
C21—C22	1.416 (2)
O5A—S1A—C30A	107.4 (3)	O4—C28—N2	119.23 (15)
C29A—S1A—C30A	100.9 (4)	N1—C1—H1	112.00
O5A—S1A—C29A	107.1 (3)	C11—C1—H1	112.00
C29B—S1B—C30B	108 (2)	C2—C1—H1	112.00
O5B—S1B—C29B	106 (2)	C3—C2—H2	110.00
O5B—S1B—C30B	119 (2)	N2—C2—H2	109.00
C7—O2—C10	118.08 (18)	C1—C2—H2	109.00
C3—N1—C4	133.80 (15)	C6—C5—H5	120.00
C1—N1—C4	129.79 (14)	C4—C5—H5	120.00
C1—N1—C3	95.78 (14)	C7—C6—H6	120.00
C2—N2—C17	117.44 (14)	C5—C6—H6	120.00
C17—N2—C28	124.63 (14)	C7—C8—H8	120.00
C2—N2—C28	117.87 (14)	C9—C8—H8	120.00
N1—C1—C11	115.59 (14)	C4—C9—H9	120.00
N1—C1—C2	86.20 (12)	C8—C9—H9	120.00
C2—C1—C11	117.03 (14)	O2—C10—H10C	109.00
C1—C2—C3	85.86 (12)	O2—C10—H10B	109.00
N2—C2—C1	120.95 (14)	H10A—C10—H10C	110.00
N2—C2—C3	119.42 (14)	O2—C10—H10A	109.00
O1—C3—N1	132.51 (17)	H10A—C10—H10B	109.00
N1—C3—C2	91.20 (14)	H10B—C10—H10C	109.00
O1—C3—C2	136.20 (17)	C11—C12—H12	120.00
N1—C4—C9	119.16 (15)	C13—C12—H12	120.00
C5—C4—C9	119.41 (17)	C14—C13—H13	120.00
N1—C4—C5	121.44 (16)	C12—C13—H13	120.00
C4—C5—C6	120.03 (19)	C14—C15—H15	121.00
C5—C6—C7	120.34 (18)	C16—C15—H15	121.00
O2—C7—C8	115.19 (17)	C11—C16—H16	120.00
C6—C7—C8	119.29 (17)	C15—C16—H16	119.00
O2—C7—C6	125.52 (18)	C20—C19—H19	120.00
C7—C8—C9	120.65 (18)	C18—C19—H19	120.00
C4—C9—C8	120.25 (18)	C21—C20—H20	120.00
C12—C11—C16	118.78 (17)	C19—C20—H20	120.00
C1—C11—C16	120.29 (16)	C22—C21—H21	120.00
C1—C11—C12	120.93 (15)	C20—C21—H21	120.00
C11—C12—C13	120.60 (17)	C26—C25—H25	120.00
C12—C13—C14	119.18 (19)	C24—C25—H25	120.00
C13—C14—C15	121.63 (19)	C27—C26—H26	120.00
Cl1—C14—C13	118.83 (17)	C25—C26—H26	120.00
Cl1—C14—C15	119.53 (16)	C22—C27—H27	120.00
C14—C15—C16	118.8 (2)	C26—C27—H27	120.00
C11—C16—C15	121.02 (19)	S1A—C29A—H29B	109.00
O3—C17—C18	123.36 (16)	H29A—C29A—H29C	109.00
O3—C17—N2	120.05 (16)	S1A—C29A—H29C	109.00
N2—C17—C18	116.58 (14)	H29A—C29A—H29B	110.00
C17—C18—C19	119.58 (15)	S1A—C29A—H29A	109.00
C17—C18—C23	119.88 (14)	H29B—C29A—H29C	110.00
C19—C18—C23	120.51 (15)	S1A—C30A—H30C	110.00
C18—C19—C20	119.98 (16)	H30A—C30A—H30C	109.00
C19—C20—C21	120.76 (16)	H30B—C30A—H30C	109.00
C20—C21—C22	120.96 (17)	H30A—C30A—H30B	109.00
C21—C22—C27	122.97 (17)	S1A—C30A—H30A	110.00
C23—C22—C27	118.61 (16)	S1A—C30A—H30B	109.00
C21—C22—C23	118.39 (15)	S1B—C29B—H29D	109.00
C22—C23—C24	119.53 (14)	S1B—C29B—H29E	110.00
C18—C23—C24	121.09 (14)	S1B—C29B—H29F	110.00
C18—C23—C22	119.37 (14)	H29D—C29B—H29E	109.00
C23—C24—C25	120.25 (15)	H29D—C29B—H29F	109.00
C25—C24—C28	119.77 (14)	H29E—C29B—H29F	110.00
C23—C24—C28	119.88 (14)	S1B—C30B—H30D	109.00
C24—C25—C26	120.21 (16)	S1B—C30B—H30E	109.00
C25—C26—C27	120.58 (18)	S1B—C30B—H30F	110.00
C22—C27—C26	120.81 (17)	H30D—C30B—H30E	109.00
N2—C28—C24	116.85 (14)	H30D—C30B—H30F	110.00
O4—C28—C24	123.89 (15)	H30E—C30B—H30F	110.00
C10—O2—C7—C6	−7.4 (3)	C6—C7—C8—C9	1.6 (3)
C10—O2—C7—C8	172.23 (19)	O2—C7—C8—C9	−178.04 (18)
C3—N1—C1—C2	−7.68 (13)	C7—C8—C9—C4	−1.2 (3)
C4—N1—C1—C11	62.4 (2)	C1—C11—C12—C13	180.00 (18)
C4—N1—C1—C2	−179.39 (17)	C16—C11—C12—C13	−0.5 (3)
C3—N1—C1—C11	−125.92 (15)	C12—C11—C16—C15	−0.3 (3)
C4—N1—C3—O1	−4.1 (4)	C1—C11—C16—C15	179.2 (2)
C1—N1—C3—C2	7.80 (14)	C11—C12—C13—C14	1.0 (3)
C4—N1—C3—C2	178.97 (19)	C12—C13—C14—C15	−0.8 (4)
C1—N1—C4—C5	176.58 (17)	C12—C13—C14—Cl1	178.46 (17)
C3—N1—C4—C5	8.0 (3)	Cl1—C14—C15—C16	−179.2 (2)
C1—N1—C4—C9	−3.5 (3)	C13—C14—C15—C16	0.0 (4)
C3—N1—C4—C9	−172.02 (19)	C14—C15—C16—C11	0.6 (4)
C1—N1—C3—O1	−175.3 (2)	O3—C17—C18—C19	9.3 (3)
C17—N2—C2—C3	−143.50 (15)	N2—C17—C18—C23	7.7 (2)
C28—N2—C2—C3	39.3 (2)	O3—C17—C18—C23	−173.05 (17)
C28—N2—C17—C18	−13.0 (2)	N2—C17—C18—C19	−169.99 (15)
C28—N2—C2—C1	−64.7 (2)	C17—C18—C23—C22	−179.03 (15)
C2—N2—C28—O4	4.7 (2)	C19—C18—C23—C24	177.96 (15)
C2—N2—C17—O3	−9.2 (2)	C17—C18—C23—C24	0.3 (2)
C17—N2—C28—O4	−172.28 (16)	C19—C18—C23—C22	−1.4 (2)
C28—N2—C17—O3	167.75 (17)	C23—C18—C19—C20	−0.1 (3)
C2—N2—C17—C18	170.06 (14)	C17—C18—C19—C20	177.60 (17)
C2—N2—C28—C24	−173.56 (14)	C18—C19—C20—C21	0.8 (3)
C17—N2—C2—C1	112.52 (17)	C19—C20—C21—C22	0.0 (3)
C17—N2—C28—C24	9.5 (2)	C20—C21—C22—C23	−1.5 (3)
N1—C1—C11—C16	−139.21 (18)	C20—C21—C22—C27	−179.41 (18)
N1—C1—C11—C12	40.3 (2)	C21—C22—C23—C24	−177.24 (15)
C2—C1—C11—C16	121.47 (19)	C27—C22—C23—C18	−179.85 (15)
C11—C1—C2—C3	123.69 (15)	C21—C22—C23—C18	2.1 (2)
N1—C1—C2—C3	6.81 (12)	C23—C22—C27—C26	0.0 (3)
C11—C1—C2—N2	−114.25 (17)	C27—C22—C23—C24	0.8 (2)
C2—C1—C11—C12	−59.0 (2)	C21—C22—C27—C26	177.94 (18)
N1—C1—C2—N2	128.87 (15)	C18—C23—C24—C28	−3.9 (2)
C1—C2—C3—O1	175.9 (2)	C22—C23—C24—C25	−0.9 (2)
N2—C2—C3—N1	−130.79 (15)	C22—C23—C24—C28	175.38 (14)
N2—C2—C3—O1	52.5 (3)	C18—C23—C24—C25	179.75 (15)
C1—C2—C3—N1	−7.35 (13)	C23—C24—C25—C26	0.2 (2)
C5—C4—C9—C8	−0.5 (3)	C25—C24—C28—N2	175.73 (15)
N1—C4—C9—C8	179.60 (17)	C23—C24—C28—O4	−178.75 (16)
C9—C4—C5—C6	1.6 (3)	C23—C24—C28—N2	−0.6 (2)
N1—C4—C5—C6	−178.42 (18)	C28—C24—C25—C26	−176.07 (16)
C4—C5—C6—C7	−1.2 (3)	C25—C24—C28—O4	−2.4 (3)
C5—C6—C7—O2	179.20 (19)	C24—C25—C26—C27	0.6 (3)
C5—C6—C7—C8	−0.4 (3)	C25—C26—C27—C22	−0.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1	0.93	2.57	3.169 (3)	122
C21—H21···O1i	0.93	2.52	3.344 (2)	148
C25—H25···O4ii	0.93	2.46	3.221 (2)	139
C30A—H30A···Cg4iii	0.96	2.88	3.818 (10)	167

Table 1

Hydrogen-bond geometry (, )

Cg4 is the centroid of the C11C16 benzene ring.

DHA	DH	HA	D A	DHA
C5H5O1	0.93	2.57	3.169(3)	122
C21H21O1i	0.93	2.52	3.344(2)	148
C25H25O4ii	0.93	2.46	3.221(2)	139
C30AH30A Cg4iii	0.96	2.88	3.818(10)	167

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