9-[(2,6-Dimethoxy-phen-oxy)carbon-yl]-10-methyl-acridinium trifluoro-methane-sulfonate.

In the crystal structure of the title compound, C(23)H(20)NO(4) (+)·CF(3)SO(3) (-), the cations are linked through C-H⋯O, C-H⋯π and π-π inter-actions [centroid-centroid distances = 3.641 (2) and 3.885 (2) Å]. The cation and the anion are held together by C-H⋯O and S-O⋯π inter-actions. The acridine ring system and the benzene ring in the cation are oriented at a dihedral angle of 8.7 (1)°. The carb-oxy group is twisted at an angle of 83.2 (1)° relative to the acridine skeleton.

Related literature

For general background, see: Adamczyk et al. (2004 ▶); Becker et al. (1999 ▶); Rak et al. (1999 ▶); Zomer & Jacquemijns (2001 ▶). For related structures, see: Sikorski et al. (2008 ▶). For mol­ecular inter­actions, see: Bianchi et al. (2004 ▶); Dorn et al. (2005 ▶); Hunter et al. (2001 ▶); Steiner (1999 ▶); Takahashi et al. (2001 ▶). For the synthesis, see: Sato (1996 ▶).

Experimental

Crystal data

C23H20NO4 +·CF3SO3 −

M = 523.48

Monoclinic,

a = 11.6803 (4) Å

b = 14.7434 (5) Å

c = 13.6286 (5) Å

β = 93.462 (4)°

V = 2342.66 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 295 K

0.55 × 0.30 × 0.02 mm

Data collection

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer

Absorption correction: multi-scan (; Oxford Diffraction, 2008 ▶) T min = 0.911, T max = 0.995

20680 measured reflections

4160 independent reflections

2274 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.109

S = 0.87

4160 reflections

328 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809007570/is2390sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007570/is2390Isup2.hkl

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

C23H20NO4+·CF3SO3−	F(000) = 1080
Mr = 523.48	Dx = 1.484 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2ybc	Cell parameters from 6747 reflections
a = 11.6803 (4) Å	θ = 3.1–29.2°
b = 14.7434 (5) Å	µ = 0.21 mm−1
c = 13.6286 (5) Å	T = 295 K
β = 93.462 (4)°	Plate, yellow
V = 2342.66 (14) Å3	0.55 × 0.30 × 0.02 mm
Z = 4

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer	4160 independent reflections
Radiation source: Enhanced (Mo) X-ray Source	2274 reflections with I > 2σ(I)
graphite	Rint = 0.045
Detector resolution: 10.4002 pixels mm-1	θmax = 25.1°, θmin = 3.1°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −17→17
Tmin = 0.911, Tmax = 0.995	l = −15→16
20680 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 0.87	w = 1/[σ2(Fo2) + (0.0672P)2] where P = (Fo2 + 2Fc2)/3
4160 reflections	(Δ/σ)max = 0.001
328 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.7814 (2)	0.40388 (17)	0.39746 (18)	0.0638 (6)
H1	0.8256	0.3737	0.4462	0.077*
C2	0.7685 (2)	0.49461 (18)	0.4029 (2)	0.0758 (8)
H2	0.8031	0.5265	0.4556	0.091*
C3	0.7034 (2)	0.54073 (18)	0.3296 (2)	0.0732 (8)
H3	0.6953	0.6033	0.3341	0.088*
C4	0.6517 (2)	0.49643 (17)	0.2521 (2)	0.0651 (7)
H4	0.6096	0.5289	0.2038	0.078*
C5	0.5619 (2)	0.2128 (2)	0.08150 (18)	0.0665 (7)
H5	0.5216	0.2437	0.0310	0.080*
C6	0.5684 (2)	0.1217 (2)	0.0792 (2)	0.0759 (8)
H6	0.5322	0.0908	0.0265	0.091*
C7	0.6277 (2)	0.07213 (19)	0.1532 (2)	0.0748 (7)
H7	0.6284	0.0091	0.1505	0.090*
C8	0.6843 (2)	0.11584 (17)	0.22920 (18)	0.0622 (6)
H8	0.7255	0.0828	0.2776	0.075*
C9	0.73852 (17)	0.26032 (15)	0.31071 (15)	0.0471 (6)
N10	0.61009 (14)	0.35392 (13)	0.16713 (13)	0.0508 (5)
C11	0.72823 (17)	0.35398 (15)	0.31827 (15)	0.0497 (6)
C12	0.66127 (18)	0.40128 (15)	0.24392 (16)	0.0503 (6)
C13	0.68078 (18)	0.21248 (15)	0.23483 (16)	0.0495 (6)
C14	0.61625 (18)	0.26140 (16)	0.16052 (16)	0.0514 (6)
C15	0.8199 (2)	0.21059 (14)	0.38169 (16)	0.0523 (6)
O16	0.77183 (12)	0.18961 (10)	0.46502 (11)	0.0556 (4)
O17	0.91548 (15)	0.19252 (14)	0.36460 (13)	0.0862 (6)
C18	0.84322 (18)	0.14411 (16)	0.53585 (15)	0.0512 (6)
C19	0.84232 (19)	0.05032 (16)	0.53766 (17)	0.0548 (6)
C20	0.9070 (2)	0.00594 (18)	0.61157 (19)	0.0657 (7)
H20	0.9073	−0.0570	0.6151	0.079*
C21	0.9708 (2)	0.0567 (2)	0.67943 (19)	0.0742 (8)
H21	1.0134	0.0270	0.7296	0.089*
C22	0.9739 (2)	0.1498 (2)	0.67584 (17)	0.0700 (7)
H22	1.0185	0.1823	0.7224	0.084*
C23	0.9101 (2)	0.19452 (17)	0.60234 (16)	0.0569 (6)
O24	0.77711 (14)	0.01014 (11)	0.46366 (12)	0.0674 (5)
C25	0.7774 (2)	−0.08702 (17)	0.4597 (2)	0.0771 (8)
H25A	0.7387	−0.1068	0.3993	0.116*
H25B	0.7386	−0.1108	0.5143	0.116*
H25C	0.8551	−0.1086	0.4629	0.116*
O26	0.90647 (16)	0.28607 (12)	0.58923 (12)	0.0754 (5)
C27	0.9977 (3)	0.3383 (2)	0.6341 (2)	0.0978 (10)
H27A	0.9918	0.3998	0.6111	0.147*
H27B	1.0698	0.3132	0.6172	0.147*
H27C	0.9932	0.3372	0.7042	0.147*
C28	0.5417 (2)	0.40504 (19)	0.09069 (19)	0.0798 (8)
H28A	0.5904	0.4472	0.0593	0.120*
H28B	0.4816	0.4376	0.1205	0.120*
H28C	0.5086	0.3635	0.0426	0.120*
S29	0.62429 (6)	0.72700 (4)	0.67537 (5)	0.0605 (2)
O30	0.6575 (2)	0.73286 (15)	0.77722 (13)	0.1141 (8)
O31	0.59056 (15)	0.81084 (11)	0.62945 (13)	0.0719 (5)
O32	0.55268 (15)	0.65261 (13)	0.64848 (15)	0.0913 (6)
C33	0.7559 (2)	0.70003 (18)	0.6202 (2)	0.0687 (7)
F34	0.79921 (14)	0.62064 (11)	0.65070 (14)	0.1050 (6)
F35	0.83549 (13)	0.76166 (12)	0.64108 (16)	0.1158 (6)
F36	0.74067 (16)	0.69624 (13)	0.52297 (12)	0.1107 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0710 (16)	0.0497 (17)	0.0707 (15)	−0.0017 (13)	0.0038 (13)	0.0012 (13)
C2	0.095 (2)	0.0490 (18)	0.0841 (19)	−0.0063 (15)	0.0125 (16)	−0.0089 (14)
C3	0.0845 (19)	0.0378 (15)	0.099 (2)	0.0033 (14)	0.0219 (17)	0.0021 (16)
C4	0.0616 (16)	0.0456 (17)	0.0894 (19)	0.0057 (12)	0.0156 (14)	0.0186 (14)
C5	0.0560 (15)	0.071 (2)	0.0721 (17)	−0.0045 (14)	−0.0009 (12)	0.0024 (15)
C6	0.0752 (18)	0.065 (2)	0.0870 (19)	−0.0106 (15)	−0.0002 (15)	−0.0110 (16)
C7	0.0789 (18)	0.0448 (16)	0.101 (2)	−0.0049 (14)	0.0100 (16)	−0.0090 (16)
C8	0.0645 (15)	0.0417 (16)	0.0806 (17)	0.0021 (12)	0.0055 (13)	0.0037 (13)
C9	0.0448 (12)	0.0396 (14)	0.0578 (13)	0.0018 (10)	0.0112 (11)	0.0103 (11)
N10	0.0406 (10)	0.0473 (13)	0.0649 (12)	0.0041 (9)	0.0070 (9)	0.0127 (10)
C11	0.0483 (13)	0.0400 (14)	0.0616 (14)	−0.0005 (11)	0.0109 (11)	0.0071 (12)
C12	0.0464 (13)	0.0385 (15)	0.0675 (15)	0.0019 (11)	0.0170 (12)	0.0087 (12)
C13	0.0456 (12)	0.0412 (15)	0.0628 (14)	−0.0006 (11)	0.0114 (11)	0.0057 (11)
C14	0.0410 (12)	0.0483 (15)	0.0658 (15)	0.0006 (11)	0.0104 (11)	0.0082 (12)
C15	0.0512 (15)	0.0434 (15)	0.0634 (15)	0.0005 (11)	0.0114 (12)	0.0072 (11)
O16	0.0543 (9)	0.0517 (10)	0.0617 (9)	0.0094 (7)	0.0104 (8)	0.0111 (8)
O17	0.0573 (11)	0.1193 (17)	0.0841 (12)	0.0260 (10)	0.0210 (9)	0.0410 (11)
C18	0.0500 (13)	0.0538 (16)	0.0505 (13)	0.0100 (12)	0.0085 (11)	0.0076 (12)
C19	0.0551 (14)	0.0506 (16)	0.0596 (15)	0.0053 (12)	0.0115 (12)	0.0081 (13)
C20	0.0700 (16)	0.0562 (17)	0.0721 (17)	0.0092 (14)	0.0144 (14)	0.0178 (14)
C21	0.0784 (19)	0.081 (2)	0.0628 (16)	0.0142 (16)	0.0023 (14)	0.0194 (16)
C22	0.0726 (17)	0.081 (2)	0.0564 (15)	0.0022 (15)	0.0027 (13)	−0.0005 (14)
C23	0.0622 (15)	0.0554 (17)	0.0542 (14)	0.0075 (13)	0.0131 (13)	0.0059 (13)
O24	0.0732 (11)	0.0490 (11)	0.0794 (11)	−0.0003 (9)	−0.0007 (9)	0.0070 (9)
C25	0.0817 (19)	0.0502 (18)	0.1008 (19)	−0.0032 (14)	0.0178 (15)	−0.0019 (15)
O26	0.0934 (13)	0.0544 (12)	0.0776 (11)	−0.0019 (10)	−0.0010 (10)	−0.0035 (9)
C27	0.126 (3)	0.083 (2)	0.0849 (19)	−0.028 (2)	0.0082 (18)	−0.0061 (17)
C28	0.0725 (18)	0.074 (2)	0.0911 (18)	0.0139 (15)	−0.0125 (14)	0.0230 (16)
S29	0.0693 (4)	0.0491 (4)	0.0639 (4)	−0.0018 (3)	0.0105 (3)	0.0018 (3)
O30	0.183 (2)	0.1048 (17)	0.0545 (11)	0.0155 (16)	0.0050 (12)	0.0030 (11)
O31	0.0811 (12)	0.0492 (11)	0.0853 (11)	0.0124 (9)	0.0036 (9)	0.0049 (9)
O32	0.0713 (12)	0.0602 (13)	0.1427 (16)	−0.0205 (10)	0.0087 (11)	0.0027 (12)
C33	0.0625 (17)	0.0533 (17)	0.089 (2)	−0.0042 (14)	−0.0076 (14)	0.0083 (14)
F34	0.0808 (11)	0.0678 (11)	0.1654 (16)	0.0192 (9)	−0.0016 (10)	0.0175 (11)
F35	0.0617 (10)	0.0977 (13)	0.1853 (18)	−0.0272 (10)	−0.0152 (10)	0.0345 (12)
F36	0.1302 (15)	0.1217 (16)	0.0842 (12)	0.0248 (11)	0.0384 (11)	−0.0103 (10)

C1—C2	1.349 (3)	C18—C23	1.377 (3)
C1—C11	1.418 (3)	C18—C19	1.383 (3)
C1—H1	0.9300	C19—O24	1.362 (3)
C2—C3	1.396 (4)	C19—C20	1.387 (3)
C2—H2	0.9300	C20—C21	1.374 (3)
C3—C4	1.353 (3)	C20—H20	0.9300
C3—H3	0.9300	C21—C22	1.374 (4)
C4—C12	1.412 (3)	C21—H21	0.9300
C4—H4	0.9300	C22—C23	1.380 (3)
C5—C6	1.345 (4)	C22—H22	0.9300
C5—C14	1.412 (3)	C23—O26	1.362 (3)
C5—H5	0.9300	O24—C25	1.433 (3)
C6—C7	1.396 (4)	C25—H25A	0.9600
C6—H6	0.9300	C25—H25B	0.9600
C7—C8	1.357 (3)	C25—H25C	0.9600
C7—H7	0.9300	O26—C27	1.423 (3)
C8—C13	1.428 (3)	C27—H27A	0.9600
C8—H8	0.9300	C27—H27B	0.9600
C9—C11	1.390 (3)	C27—H27C	0.9600
C9—C13	1.392 (3)	C28—H28A	0.9600
C9—C15	1.506 (3)	C28—H28B	0.9600
N10—C12	1.366 (3)	C28—H28C	0.9600
N10—C14	1.369 (3)	S29—O32	1.4142 (19)
N10—C28	1.480 (3)	S29—O30	1.421 (2)
C11—C12	1.424 (3)	S29—O31	1.4300 (17)
C13—C14	1.422 (3)	S29—C33	1.796 (3)
C15—O17	1.184 (2)	C33—F35	1.319 (3)
C15—O16	1.334 (2)	C33—F36	1.327 (3)
O16—C18	1.407 (2)	C33—F34	1.332 (3)
C2—C1—C11	120.8 (2)	C19—C18—O16	118.9 (2)
C2—C1—H1	119.6	O24—C19—C18	115.2 (2)
C11—C1—H1	119.6	O24—C19—C20	126.1 (2)
C1—C2—C3	120.1 (3)	C18—C19—C20	118.7 (2)
C1—C2—H2	120.0	C21—C20—C19	118.8 (2)
C3—C2—H2	120.0	C21—C20—H20	120.6
C4—C3—C2	121.5 (2)	C19—C20—H20	120.6
C4—C3—H3	119.3	C20—C21—C22	122.3 (2)
C2—C3—H3	119.3	C20—C21—H21	118.8
C3—C4—C12	120.5 (2)	C22—C21—H21	118.8
C3—C4—H4	119.7	C21—C22—C23	119.3 (3)
C12—C4—H4	119.7	C21—C22—H22	120.4
C6—C5—C14	120.1 (2)	C23—C22—H22	120.4
C6—C5—H5	119.9	O26—C23—C18	115.9 (2)
C14—C5—H5	119.9	O26—C23—C22	125.5 (2)
C5—C6—C7	122.1 (3)	C18—C23—C22	118.7 (2)
C5—C6—H6	118.9	C19—O24—C25	117.39 (19)
C7—C6—H6	118.9	O24—C25—H25A	109.5
C8—C7—C6	120.0 (2)	O24—C25—H25B	109.5
C8—C7—H7	120.0	H25A—C25—H25B	109.5
C6—C7—H7	120.0	O24—C25—H25C	109.5
C7—C8—C13	120.0 (2)	H25A—C25—H25C	109.5
C7—C8—H8	120.0	H25B—C25—H25C	109.5
C13—C8—H8	120.0	C23—O26—C27	117.6 (2)
C11—C9—C13	121.2 (2)	O26—C27—H27A	109.5
C11—C9—C15	119.3 (2)	O26—C27—H27B	109.5
C13—C9—C15	119.3 (2)	H27A—C27—H27B	109.5
C12—N10—C14	122.52 (18)	O26—C27—H27C	109.5
C12—N10—C28	118.1 (2)	H27A—C27—H27C	109.5
C14—N10—C28	119.28 (19)	H27B—C27—H27C	109.5
C9—C11—C1	122.4 (2)	N10—C28—H28A	109.5
C9—C11—C12	118.7 (2)	N10—C28—H28B	109.5
C1—C11—C12	118.9 (2)	H28A—C28—H28B	109.5
N10—C12—C4	122.4 (2)	N10—C28—H28C	109.5
N10—C12—C11	119.4 (2)	H28A—C28—H28C	109.5
C4—C12—C11	118.2 (2)	H28B—C28—H28C	109.5
C9—C13—C14	119.0 (2)	O32—S29—O30	115.00 (13)
C9—C13—C8	122.1 (2)	O32—S29—O31	114.45 (12)
C14—C13—C8	118.9 (2)	O30—S29—O31	115.25 (12)
N10—C14—C5	122.2 (2)	O32—S29—C33	103.15 (12)
N10—C14—C13	119.1 (2)	O30—S29—C33	103.43 (14)
C5—C14—C13	118.7 (2)	O31—S29—C33	103.20 (11)
O17—C15—O16	124.5 (2)	F35—C33—F36	107.1 (2)
O17—C15—C9	123.3 (2)	F35—C33—F34	106.8 (2)
O16—C15—C9	112.20 (19)	F36—C33—F34	107.5 (2)
C15—O16—C18	115.60 (16)	F35—C33—S29	111.5 (2)
C23—C18—C19	122.2 (2)	F36—C33—S29	111.15 (18)
C23—C18—O16	118.9 (2)	F34—C33—S29	112.49 (19)
C11—C1—C2—C3	−0.7 (4)	C8—C13—C14—C5	−2.7 (3)
C1—C2—C3—C4	0.2 (4)	C11—C9—C15—O17	−94.4 (3)
C2—C3—C4—C12	0.8 (4)	C13—C9—C15—O17	81.4 (3)
C14—C5—C6—C7	0.1 (4)	C11—C9—C15—O16	85.7 (2)
C5—C6—C7—C8	−2.1 (4)	C13—C9—C15—O16	−98.5 (2)
C6—C7—C8—C13	1.7 (4)	O17—C15—O16—C18	1.0 (3)
C13—C9—C11—C1	176.74 (19)	C9—C15—O16—C18	−179.09 (18)
C15—C9—C11—C1	−7.6 (3)	C15—O16—C18—C23	88.2 (2)
C13—C9—C11—C12	−2.9 (3)	C15—O16—C18—C19	−93.1 (2)
C15—C9—C11—C12	172.79 (19)	C23—C18—C19—O24	−176.27 (18)
C2—C1—C11—C9	−179.3 (2)	O16—C18—C19—O24	5.0 (3)
C2—C1—C11—C12	0.3 (3)	C23—C18—C19—C20	2.9 (3)
C14—N10—C12—C4	−177.94 (19)	O16—C18—C19—C20	−175.80 (18)
C28—N10—C12—C4	−0.5 (3)	O24—C19—C20—C21	178.2 (2)
C14—N10—C12—C11	2.9 (3)	C18—C19—C20—C21	−0.9 (3)
C28—N10—C12—C11	−179.61 (19)	C19—C20—C21—C22	−0.9 (4)
C3—C4—C12—N10	179.7 (2)	C20—C21—C22—C23	0.7 (4)
C3—C4—C12—C11	−1.1 (3)	C19—C18—C23—O26	177.12 (18)
C9—C11—C12—N10	−0.6 (3)	O16—C18—C23—O26	−4.2 (3)
C1—C11—C12—N10	179.75 (18)	C19—C18—C23—C22	−3.1 (3)
C9—C11—C12—C4	−179.77 (18)	O16—C18—C23—C22	175.59 (18)
C1—C11—C12—C4	0.6 (3)	C21—C22—C23—O26	−179.0 (2)
C11—C9—C13—C14	4.1 (3)	C21—C22—C23—C18	1.3 (3)
C15—C9—C13—C14	−171.59 (19)	C18—C19—O24—C25	177.29 (18)
C11—C9—C13—C8	−175.94 (19)	C20—C19—O24—C25	−1.8 (3)
C15—C9—C13—C8	8.4 (3)	C18—C23—O26—C27	−160.7 (2)
C7—C8—C13—C9	−179.3 (2)	C22—C23—O26—C27	19.5 (3)
C7—C8—C13—C14	0.7 (3)	O32—S29—C33—F35	−177.69 (18)
C12—N10—C14—C5	179.21 (18)	O30—S29—C33—F35	−57.6 (2)
C28—N10—C14—C5	1.8 (3)	O31—S29—C33—F35	62.9 (2)
C12—N10—C14—C13	−1.7 (3)	O32—S29—C33—F36	62.8 (2)
C28—N10—C14—C13	−179.15 (19)	O30—S29—C33—F36	−177.05 (19)
C6—C5—C14—N10	−178.6 (2)	O31—S29—C33—F36	−56.6 (2)
C6—C5—C14—C13	2.3 (3)	O32—S29—C33—F34	−57.7 (2)
C9—C13—C14—N10	−1.8 (3)	O30—S29—C33—F34	62.4 (2)
C8—C13—C14—N10	178.23 (18)	O31—S29—C33—F34	−177.18 (18)
C9—C13—C14—C5	177.31 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O30i	0.93	2.57	3.449 (3)	158
C4—H4···O31i	0.93	2.58	3.352 (3)	141
C7—H7···O32ii	0.93	2.54	3.427 (3)	159
C27—H27C···O17iii	0.96	2.46	3.371 (3)	159
C25—H25C···Cg4iv	0.96	2.98	3.845 (3)	150

X	I	J	I···J	X···J	X—I···J
S29	O31	Cg3v	3.968 (2)	4.111 (2)	85
S29	O32	Cg1v	3.178 (2)	3.757 (2)	103
S29	O32	Cg2v	3.512 (2)	4.741 (2)	145

I	J	CgI···CgJ	Dihedral angle	CgIPerp	CgJPerp	CgIOffset	CgJOffset
1	4ii	3.641 (2)	5.31 (10)	3.416 (2)	3.492 (2)	0.767 (2)	1.031 (2)
2	4ii	3.885 (2)	6.74 (11)	3.666 (2)	3.491 (2)	1.286 (2)	1.705 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O30i	0.93	2.57	3.449 (3)	158
C4—H4⋯O31i	0.93	2.58	3.352 (3)	141
C7—H7⋯O32ii	0.93	2.54	3.427 (3)	159
C27—H27C⋯O17iii	0.96	2.46	3.371 (3)	159
C25—H25C⋯Cg4iv	0.96	2.98	3.845 (3)	150

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg4 is the centroid of the C18–C23 ring.

Table 2

S—O⋯π Interactions (Å,°)

X	I	J	I⋯J	X⋯J	X—I⋯J
S29	O32	Cg1v	3.178 (2)	3.757 (2)	103

Symmetry codes: (v) –x+1, –y+1, –z+1. Cg1 is the centroid of the C9/N10/C11–C14 ring.

Table 3

π–π Interactions (Å,°)

I	J	CgI⋯CgJ	Dihedral angle	CgIPerp	CgJPerp	CgIOffset	CgJOffset
1	4ii	3.641 (2)	5.31 (10)	3.416 (2)	3.492 (2)	0.767 (2)	1.031 (2)
2	4ii	3.885 (2)	6.74 (11)	3.666 (2)	3.491 (2)	1.286 (2)	1.705 (2)

Symmetry code: (ii) . Notes: Cg1, Cg2 and Cg4 are the centroids of the C9/N10/C11–C14, C1–C4/C11/C12 and C18–C23 rings, respectively. CgI⋯CgJ is the distance between ring centroids. The dihedral angle is that between the planes of the rings I and J. CgI Perp and CgJ Perp are the perpendicular distances of CgI from ring J and of CgJ from ring I, respectively. CgI Offset and CgJ Offset are the distances between CgI and the perpendicular projection of CgJ on ring I, and between CgJ and the perpendicular projection of CgI on ring J, respectively.