2-[(E)-2-(3-Hydr­oxy-4-methoxy­phen­yl)ethen­yl]-1-methyl­quinolinium 4-methyl­benzene­sulfonate

In the title compound, C₁₉H₁₈NO₂⁺. C₇H₇SO₃⁻, the cation is almost planar and the benzene ring of the anion makes dihedral angles of 59.17 (9) and 60.59 (10)° with the mean planes through the quinolinium and benzene ring of the cation, respectively. The cations and anions are packed as alternate layers along the b axis. These layers are inter­connected through O—H...O and C—H...O inter­actions to form a three-dimensional network. The structure is stabilized by these inter­actions and C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.107
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N1     -   C20     ..       5.63 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C15    -   C16     ..       6.33 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C17    -   C18     ..       5.38 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C18    -   C19     ..       6.91 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C5     -   C6      ..       5.51 su
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H15A   ..  H26A    ..       1.80 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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S1. Comment

The search for new organic materials that exhibit large molecular second-order optical nonlinearities is of considerable interest because of their wide range of potential applications, such as in the frequency doubling of lasers and optical data storage applications (Chemla & Zyss, 1987; Marder et al., 1991; Usman et al., 2000; Umezawa et al., 2002; Feng et al., 2005; Ye et al., 2005). Some organic materials are transparent in the visible region, which is good for nonlinear optical (NLO) materials compared with inorganic crystals [what exactly is being compared here?] (Chemla & Zyss, 1987; Chia et al., 1995; Zhengdong et al., 1997). An organic crystal with delocalized π-electrons usually displays a large NLO response (Prasad & William, 1991). Most of these crystals are composed of aromatic molecules that are substituted with π-electron donors and acceptors, which exhibit intramolecular charge transfer. One generally successful and popular approach to obtaining NLO materials is to find a substance that crystallizes in a non-centrosymmetric space group. Oudar & LePerson (1975) have also reported the effect of conjugation length, using stilbene instead of a benzene π-system. In our continuing research on NLO materials (Rahman et al., 2003; Jindawong et al., 2005; Chantrapromma et al., 2005), we expected that the two rings of quinoline, with the ethylenic C═C lying in the same molecular plane, would change the molecular packing from centrosymmetric, as in our previous report (Rahman et al., 2003), to non-centrosymmetric. For this reason, the title compound, (I), was designed and synthesized. The X-ray study of (I) was carried out in order to obtain detailed information on its crystal structure.

Compound (I) is found to crystallize in the centrosymmetric space group P2₁/n and, therefore, has no second-order nonlinear optical properties. The molecular structure of (I) is illustrated in Fig. 1, and selected bond distances and angles are given in Table 1. The asymmetric unit of (I) consists of a C₁₉H₁₈NO₂⁺ cation and a C₇H₇SO₃⁻ anion. The quinolinium ring system [C16–C24/N1] is essentially planar, with a maximum deviation of 0.029 (2) Å for atom N1. The H atoms attached to C14 and C15 are trans to each other; thus the cation exists in an E configuration [the C13—C14—C15—C16 torsion angle is −178.1 (2)°]. The bond distances and angles (Table 1) in both the cation and the anion have normal values (Allen et al., 1987) and are comparable to those in a related structure (Rahman et al., 2003). The cation is almost planar, the dihedral angle between the benzene and quinolinium rings being 2.59 (9)°. The methoxy substituent deviates slightly from the plane of the benzene ring, with torsion angles of 7.5 (3)° for C25—O4—C10—C9 and 177.0 (2)° for C8—C9—C10—O4. The benzene ring in the 4-methylbenzenesulfonate anion makes dihedral angles of 60.59 (10)° with the benzene ring of the cation and 59.17 (9)° with the quinolinium ring system.

In the crystal structure, atoms O2 and O3 of the anion are involved in weak C—H···O interactions, while atom O1 is involved in O—H···O hydrogen bonds (Table 2). The molecules form alternate layers of cations and anions along the b axis. These layers are interconnected through O—H···O hydrogen bonds and weak C—H···O interactions to form a three-dimensional network (Fig. 2 and Table 2). The crystal structure is further stabilized by C—H···π interactions involving the centroid, Cg1, of the benzene ring (C8–C13) of the cation (Table 2).

S2. Experimental

2-[(4-Methoxy-3-hydroxyphenyl)ethenyl]-N-methylquinolinium iodide (compound A) was synthesized from a mixture (1:1:1 molar ratio) of N-2-dimethylquinolinium iodide (1.98 g, 6.94 mmol), isovanillin (1.06 g, 6.94 mmol) and piperidine (0.60 g, 7.09 mmol) in methanol under reflux for 2 h in a nitrogen atmosphere. The solid that formed was filtered, washed with diethyl ether and recrystallized from methanol to give red–brown crystals of compound A (2.00 g, 68%, m.p. 491–493 K). The title compound was synthesized by mixing compound A (0.30 g, 0.72 mmol) in hot methanol (50 ml) and a solution of silver(I) p-toluenesulfonate (compound B) (0.20 g, 0.72 mmol) in hot methanol (30 ml), in a manner similar to that previously reported (Rahman et al., 2003). The mixing immediately yielded a yellow solid of silver iodide. After stirring the mixture for 30 min, the precipitate of silver iodide was removed and the resulting solution was evaporated to yield an orange solid. Colorless single crystals of (I) suitable for X-ray data collection were obtained by recrystallization from methanol and dichloromethane (1:1) after several days at ambient temperature (m.p. 526–528 K).

S3. Refinement

H atoms were placed in calculated positions, with an O—H distance of 0.82 Å and C—H distances in the range 0.93–0.96 Å. The U_iso(H) values were constrained to be 1.5U_eq of the carrier atom for hydroxyl and methyl H atoms, and 1.2U_eq(C) for the remaining H atoms.

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Figures

	Fig. 1. The asymmetric unit of (I), showing 50% probability displacement ellipsoids and the atomic numbering.
	Fig. 2. The crystal packing of (I), viewed down the a axis. Hydrogen bonds are shown as dashed lines.

2-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-1-methylquinolinium 4-methylbenzenesulfonate

Crystal data

C19H18NO2^+·C7H7O3S^−	F(000) = 976
Mr = 463.54	Dx = 1.386 Mg m^−3
Monoclinic, P21/n	Melting point: 526-528 K K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.3382 (3) Å	Cell parameters from 3913 reflections
b = 21.8714 (7) Å	θ = 1.7–25.0°
c = 14.0755 (4) Å	µ = 0.19 mm^−1
β = 100.464 (1)°	T = 273 K
V = 2221.50 (13) Å^3	Needle, colorless
Z = 4	0.50 × 0.24 × 0.10 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	3913 independent reflections
Radiation source: fine-focus sealed tube	3138 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 8.33 pixels mm^-1	θmax = 25.0°, θmin = 1.7°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −26→26
Tmin = 0.948, Tmax = 0.982	l = −16→16
17716 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.107	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0408P)^2 + 1.1272P] where P = (Fo^2 + 2Fc^2)/3
3913 reflections	(Δ/σ)max < 0.001
301 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.21121 (8)	0.16748 (2)	0.86833 (4)	0.04970 (17)
O1	0.3052 (2)	0.12978 (6)	0.80647 (11)	0.0569 (4)
O2	0.3161 (2)	0.22217 (7)	0.89906 (12)	0.0657 (5)
O3	0.1547 (3)	0.13322 (8)	0.94541 (12)	0.0771 (5)
O4	0.3507 (2)	−0.08651 (7)	0.67204 (11)	0.0578 (4)
O5	0.2446 (3)	0.01927 (7)	0.72949 (10)	0.0642 (5)
H5A	0.2643	0.0529	0.7551	0.096*
N1	0.1834 (2)	0.05830 (8)	1.23275 (12)	0.0456 (4)
C1	−0.1636 (3)	0.21975 (10)	0.63561 (16)	0.0562 (6)
H1B	−0.1631	0.2281	0.5709	0.067*
C2	−0.0005 (3)	0.20294 (10)	0.69551 (15)	0.0499 (5)
H2B	0.1079	0.1994	0.6705	0.060*
C3	0.0025 (3)	0.19130 (8)	0.79222 (14)	0.0428 (5)
C4	−0.1584 (3)	0.19784 (10)	0.82875 (16)	0.0526 (5)
H4A	−0.1575	0.1913	0.8941	0.063*
C5	−0.3219 (3)	0.21418 (10)	0.76789 (19)	0.0590 (6)
H5B	−0.4299	0.2184	0.7931	0.071*
C6	−0.3270 (3)	0.22436 (9)	0.67048 (17)	0.0541 (6)
C7	−0.5062 (4)	0.23937 (13)	0.6036 (2)	0.0832 (9)
H7A	−0.4818	0.2665	0.5538	0.125*
H7B	−0.5894	0.2587	0.6396	0.125*
H7C	−0.5614	0.2024	0.5749	0.125*
C8	0.3722 (3)	−0.11875 (9)	0.93061 (16)	0.0489 (5)
H8A	0.4047	−0.1501	0.9752	0.059*
C9	0.3810 (3)	−0.12874 (9)	0.83454 (16)	0.0492 (5)
H9A	0.4154	−0.1670	0.8149	0.059*
C10	0.3389 (3)	−0.08230 (9)	0.76733 (14)	0.0434 (5)
C11	0.2835 (3)	−0.02523 (9)	0.79783 (14)	0.0435 (5)
C12	0.2707 (3)	−0.01618 (9)	0.89273 (14)	0.0422 (5)
H12A	0.2313	0.0215	0.9118	0.051*
C13	0.3158 (3)	−0.06265 (9)	0.96163 (14)	0.0422 (5)
C14	0.3060 (3)	−0.05346 (10)	1.06274 (15)	0.0477 (5)
H14A	0.3510	−0.0848	1.1053	0.057*
C15	0.2390 (3)	−0.00457 (10)	1.09990 (15)	0.0512 (5)
H15A	0.1904	0.0264	1.0576	0.061*
C16	0.2358 (3)	0.00430 (10)	1.20185 (15)	0.0488 (5)
C17	0.2878 (4)	−0.04360 (11)	1.27052 (16)	0.0631 (7)
H17A	0.3243	−0.0814	1.2502	0.076*
C18	0.2838 (4)	−0.03394 (11)	1.36477 (17)	0.0677 (7)
H18A	0.3202	−0.0652	1.4089	0.081*
C19	0.2262 (3)	0.02209 (10)	1.39784 (16)	0.0547 (6)
C20	0.1719 (3)	0.06925 (10)	1.33037 (14)	0.0458 (5)
C21	0.1112 (3)	0.12459 (11)	1.36057 (16)	0.0570 (6)
H21A	0.0732	0.1555	1.3161	0.068*
C22	0.1074 (4)	0.13341 (12)	1.45562 (17)	0.0656 (7)
H22A	0.0668	0.1708	1.4754	0.079*
C23	0.1623 (4)	0.08839 (12)	1.52421 (17)	0.0695 (7)
H23A	0.1596	0.0960	1.5890	0.083*
C24	0.2199 (4)	0.03323 (12)	1.49671 (16)	0.0669 (7)
H24A	0.2553	0.0028	1.5425	0.080*
C25	0.3891 (4)	−0.14492 (11)	0.63538 (18)	0.0652 (7)
H25A	0.3875	−0.1419	0.5672	0.098*
H25D	0.2967	−0.1737	0.6470	0.098*
H25B	0.5091	−0.1585	0.6673	0.098*
C26	0.1381 (3)	0.10910 (10)	1.16524 (15)	0.0513 (5)
H26A	0.1908	0.1017	1.1087	0.077*
H26B	0.1879	0.1463	1.1955	0.077*
H26C	0.0060	0.1127	1.1472	0.077*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0637 (4)	0.0393 (3)	0.0457 (3)	0.0077 (2)	0.0090 (2)	0.0040 (2)
O1	0.0649 (10)	0.0399 (8)	0.0673 (10)	0.0087 (7)	0.0163 (8)	−0.0031 (7)
O2	0.0725 (11)	0.0487 (9)	0.0682 (10)	0.0061 (8)	−0.0078 (8)	−0.0121 (8)
O3	0.0945 (14)	0.0815 (12)	0.0587 (10)	0.0195 (10)	0.0230 (9)	0.0306 (9)
O4	0.0816 (11)	0.0435 (8)	0.0511 (9)	−0.0038 (8)	0.0199 (8)	−0.0106 (7)
O5	0.1076 (14)	0.0405 (8)	0.0433 (8)	0.0049 (8)	0.0108 (8)	0.0011 (7)
N1	0.0446 (10)	0.0454 (10)	0.0455 (10)	−0.0033 (8)	0.0046 (8)	0.0067 (8)
C1	0.0685 (16)	0.0525 (13)	0.0463 (12)	−0.0013 (11)	0.0066 (11)	−0.0006 (10)
C2	0.0559 (14)	0.0504 (13)	0.0458 (12)	0.0019 (10)	0.0156 (10)	−0.0001 (10)
C3	0.0561 (13)	0.0300 (10)	0.0434 (11)	−0.0017 (9)	0.0123 (9)	−0.0010 (8)
C4	0.0643 (15)	0.0459 (12)	0.0512 (12)	−0.0047 (11)	0.0198 (11)	−0.0012 (10)
C5	0.0529 (14)	0.0462 (13)	0.0823 (17)	−0.0037 (11)	0.0243 (12)	−0.0054 (12)
C6	0.0576 (14)	0.0367 (11)	0.0657 (15)	−0.0033 (10)	0.0048 (11)	−0.0045 (10)
C7	0.0632 (17)	0.0733 (18)	0.103 (2)	−0.0011 (14)	−0.0120 (15)	−0.0069 (16)
C8	0.0507 (13)	0.0396 (11)	0.0553 (13)	0.0047 (9)	0.0068 (10)	0.0083 (9)
C9	0.0493 (13)	0.0351 (11)	0.0643 (14)	0.0034 (9)	0.0130 (10)	−0.0049 (10)
C10	0.0439 (11)	0.0410 (11)	0.0457 (11)	−0.0069 (9)	0.0094 (9)	−0.0063 (9)
C11	0.0501 (12)	0.0347 (10)	0.0444 (11)	−0.0029 (9)	0.0056 (9)	−0.0006 (9)
C12	0.0462 (12)	0.0335 (10)	0.0462 (11)	−0.0011 (9)	0.0066 (9)	−0.0043 (8)
C13	0.0387 (11)	0.0418 (11)	0.0450 (11)	−0.0036 (9)	0.0042 (9)	0.0000 (9)
C14	0.0497 (13)	0.0467 (12)	0.0451 (11)	−0.0043 (10)	0.0046 (9)	0.0056 (9)
C15	0.0617 (14)	0.0491 (13)	0.0405 (11)	0.0024 (10)	0.0033 (10)	0.0014 (10)
C16	0.0469 (12)	0.0449 (12)	0.0522 (12)	−0.0043 (10)	0.0027 (10)	−0.0025 (10)
C17	0.0925 (19)	0.0500 (13)	0.0447 (13)	0.0060 (13)	0.0066 (12)	0.0057 (10)
C18	0.093 (2)	0.0544 (15)	0.0511 (14)	0.0014 (13)	0.0018 (13)	0.0152 (11)
C19	0.0591 (14)	0.0507 (13)	0.0534 (13)	−0.0073 (11)	0.0080 (11)	−0.0012 (10)
C20	0.0429 (12)	0.0566 (13)	0.0369 (11)	−0.0099 (10)	0.0047 (9)	0.0034 (9)
C21	0.0611 (15)	0.0572 (14)	0.0524 (13)	−0.0008 (11)	0.0097 (11)	0.0034 (11)
C22	0.0758 (17)	0.0663 (16)	0.0558 (14)	−0.0016 (13)	0.0146 (12)	−0.0074 (12)
C23	0.095 (2)	0.0736 (17)	0.0423 (13)	−0.0036 (15)	0.0177 (13)	−0.0060 (12)
C24	0.0874 (19)	0.0693 (17)	0.0427 (13)	−0.0070 (14)	0.0084 (12)	0.0091 (11)
C25	0.0788 (18)	0.0528 (14)	0.0656 (15)	−0.0022 (12)	0.0174 (13)	−0.0221 (12)
C26	0.0600 (14)	0.0499 (13)	0.0435 (11)	0.0047 (10)	0.0081 (10)	0.0068 (10)

Geometric parameters (Å, º)

S1—O3	1.4402 (17)	C10—C11	1.404 (3)
S1—O2	1.4453 (17)	C11—C12	1.371 (3)
S1—O1	1.4600 (15)	C12—C13	1.402 (3)
S1—C3	1.780 (2)	C12—H12A	0.9300
O4—C10	1.363 (2)	C13—C14	1.452 (3)
O4—C25	1.425 (3)	C14—C15	1.324 (3)
O5—C11	1.362 (2)	C14—H14A	0.9300
O5—H5A	0.8200	C15—C16	1.452 (3)
N1—C16	1.339 (3)	C15—H15A	0.9300
N1—C20	1.412 (3)	C16—C17	1.429 (3)
N1—C26	1.461 (3)	C17—C18	1.349 (3)
C1—C6	1.379 (3)	C17—H17A	0.9300
C1—C2	1.383 (3)	C18—C19	1.403 (3)
C1—H1B	0.9300	C18—H18A	0.9300
C2—C3	1.381 (3)	C19—C20	1.410 (3)
C2—H2B	0.9300	C19—C24	1.422 (3)
C3—C4	1.378 (3)	C20—C21	1.383 (3)
C4—C5	1.388 (3)	C21—C22	1.357 (3)
C4—H4A	0.9300	C21—H21A	0.9300
C5—C6	1.383 (3)	C22—C23	1.387 (3)
C5—H5B	0.9300	C22—H22A	0.9300
C6—C7	1.507 (3)	C23—C24	1.358 (4)
C7—H7A	0.9600	C23—H23A	0.9300
C7—H7B	0.9600	C24—H24A	0.9300
C7—H7C	0.9600	C25—H25A	0.9600
C8—C9	1.383 (3)	C25—H25D	0.9600
C8—C13	1.391 (3)	C25—H25B	0.9600
C8—H8A	0.9300	C26—H26A	0.9600
C9—C10	1.384 (3)	C26—H26B	0.9600
C9—H9A	0.9300	C26—H26C	0.9600
O3—S1—O2	114.56 (11)	C13—C12—H12A	119.3
O3—S1—O1	112.80 (10)	C8—C13—C12	117.95 (18)
O2—S1—O1	111.25 (10)	C8—C13—C14	120.03 (18)
O3—S1—C3	105.76 (10)	C12—C13—C14	122.02 (18)
O2—S1—C3	106.91 (9)	C15—C14—C13	125.9 (2)
O1—S1—C3	104.74 (9)	C15—C14—H14A	117.0
C10—O4—C25	117.98 (17)	C13—C14—H14A	117.0
C11—O5—H5A	109.5	C14—C15—C16	124.9 (2)
C16—N1—C20	122.49 (17)	C14—C15—H15A	117.6
C16—N1—C26	120.29 (17)	C16—C15—H15A	117.6
C20—N1—C26	117.21 (17)	N1—C16—C17	118.9 (2)
C6—C1—C2	121.0 (2)	N1—C16—C15	119.73 (19)
C6—C1—H1B	119.5	C17—C16—C15	121.3 (2)
C2—C1—H1B	119.5	C18—C17—C16	120.0 (2)
C3—C2—C1	120.5 (2)	C18—C17—H17A	120.0
C3—C2—H2B	119.8	C16—C17—H17A	120.0
C1—C2—H2B	119.8	C17—C18—C19	121.6 (2)
C4—C3—C2	119.2 (2)	C17—C18—H18A	119.2
C4—C3—S1	120.51 (16)	C19—C18—H18A	119.2
C2—C3—S1	120.34 (17)	C18—C19—C20	118.7 (2)
C3—C4—C5	119.9 (2)	C18—C19—C24	122.7 (2)
C3—C4—H4A	120.0	C20—C19—C24	118.6 (2)
C5—C4—H4A	120.0	C21—C20—C19	120.04 (19)
C6—C5—C4	121.2 (2)	C21—C20—N1	121.80 (19)
C6—C5—H5B	119.4	C19—C20—N1	118.1 (2)
C4—C5—H5B	119.4	C22—C21—C20	119.5 (2)
C1—C6—C5	118.2 (2)	C22—C21—H21A	120.2
C1—C6—C7	120.7 (2)	C20—C21—H21A	120.2
C5—C6—C7	121.2 (2)	C21—C22—C23	122.0 (2)
C6—C7—H7A	109.5	C21—C22—H22A	119.0
C6—C7—H7B	109.5	C23—C22—H22A	119.0
H7A—C7—H7B	109.5	C24—C23—C22	119.9 (2)
C6—C7—H7C	109.5	C24—C23—H23A	120.0
H7A—C7—H7C	109.5	C22—C23—H23A	120.0
H7B—C7—H7C	109.5	C23—C24—C19	119.9 (2)
C9—C8—C13	121.06 (19)	C23—C24—H24A	120.1
C9—C8—H8A	119.5	C19—C24—H24A	120.1
C13—C8—H8A	119.5	O4—C25—H25A	109.5
C8—C9—C10	120.55 (19)	O4—C25—H25D	109.5
C8—C9—H9A	119.7	H25A—C25—H25D	109.5
C10—C9—H9A	119.7	O4—C25—H25B	109.5
O4—C10—C9	125.23 (18)	H25A—C25—H25B	109.5
O4—C10—C11	115.78 (18)	H25D—C25—H25B	109.5
C9—C10—C11	118.98 (19)	N1—C26—H26A	109.5
O5—C11—C12	122.85 (18)	N1—C26—H26B	109.5
O5—C11—C10	117.05 (18)	H26A—C26—H26B	109.5
C12—C11—C10	120.10 (18)	N1—C26—H26C	109.5
C11—C12—C13	121.34 (18)	H26A—C26—H26C	109.5
C11—C12—H12A	119.3	H26B—C26—H26C	109.5
C6—C1—C2—C3	−1.0 (3)	C11—C12—C13—C14	178.90 (19)
C1—C2—C3—C4	−1.3 (3)	C8—C13—C14—C15	−173.5 (2)
C1—C2—C3—S1	178.13 (16)	C12—C13—C14—C15	6.9 (3)
O3—S1—C3—C4	25.5 (2)	C13—C14—C15—C16	−178.1 (2)
O2—S1—C3—C4	−97.00 (18)	C20—N1—C16—C17	−2.0 (3)
O1—S1—C3—C4	144.86 (17)	C26—N1—C16—C17	177.0 (2)
O3—S1—C3—C2	−153.92 (17)	C20—N1—C16—C15	178.03 (18)
O2—S1—C3—C2	83.59 (18)	C26—N1—C16—C15	−2.9 (3)
O1—S1—C3—C2	−34.55 (19)	C14—C15—C16—N1	172.7 (2)
C2—C3—C4—C5	1.9 (3)	C14—C15—C16—C17	−7.3 (4)
S1—C3—C4—C5	−177.54 (16)	N1—C16—C17—C18	−0.1 (4)
C3—C4—C5—C6	−0.2 (3)	C15—C16—C17—C18	179.8 (2)
C2—C1—C6—C5	2.6 (3)	C16—C17—C18—C19	1.2 (4)
C2—C1—C6—C7	−176.7 (2)	C17—C18—C19—C20	−0.2 (4)
C4—C5—C6—C1	−2.0 (3)	C17—C18—C19—C24	179.7 (3)
C4—C5—C6—C7	177.3 (2)	C18—C19—C20—C21	178.8 (2)
C13—C8—C9—C10	2.0 (3)	C24—C19—C20—C21	−1.0 (3)
C25—O4—C10—C9	7.5 (3)	C18—C19—C20—N1	−1.8 (3)
C25—O4—C10—C11	−174.14 (19)	C24—C19—C20—N1	178.3 (2)
C8—C9—C10—O4	177.0 (2)	C16—N1—C20—C21	−177.6 (2)
C8—C9—C10—C11	−1.3 (3)	C26—N1—C20—C21	3.3 (3)
O4—C10—C11—O5	1.1 (3)	C16—N1—C20—C19	3.0 (3)
C9—C10—C11—O5	179.60 (18)	C26—N1—C20—C19	−176.05 (19)
O4—C10—C11—C12	−178.86 (18)	C19—C20—C21—C22	1.1 (3)
C9—C10—C11—C12	−0.4 (3)	N1—C20—C21—C22	−178.2 (2)
O5—C11—C12—C13	−178.58 (19)	C20—C21—C22—C23	−0.2 (4)
C10—C11—C12—C13	1.4 (3)	C21—C22—C23—C24	−0.8 (4)
C9—C8—C13—C12	−1.0 (3)	C22—C23—C24—C19	0.8 (4)
C9—C8—C13—C14	179.41 (19)	C18—C19—C24—C23	−179.8 (3)
C11—C12—C13—C8	−0.7 (3)	C20—C19—C24—C23	0.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O1	0.82	1.83	2.653 (2)	177
C5—H5B···O2^i	0.93	2.59	3.504 (3)	167
C12—H12A···O3	0.93	2.57	3.490 (3)	171
C23—H23A···O5^ii	0.93	2.58	3.219 (3)	126
C25—H25D···O2^iii	0.96	2.47	3.269 (3)	141
C26—H26A···O3	0.96	2.37	3.163 (3)	140
C26—H26C···Cg1^iv	0.96	2.58	3.458 (2)	153

Symmetry codes: (i) x−1, y, z; (ii) x, y, z+1; (iii) −x+1/2, y−1/2, −z+3/2; (iv) −x, −y, −z+2.