(E)-4-Chloro-2-[(2,3-dimethyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazol-4-yl)imino­meth­yl]-6-methoxy­phenyl 4-methyl­benzene­sulfonate acetonitrile solvate

In the title compound, C₂₆H₂₄ClN₃O₅S·C₂H₃N, the o-vanillin group makes dihedral angles of 25.87 (4), 11.93 (3) and 72.05 (7)° with the pyrazolone, benzene and phenyl rings, respectively. The crystal structure is stabilized by weak inter­molecular C—H...O inter­actions that link mol­ecules into centrosymmetric dimers.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.044
• wR factor = 0.133
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        200 Deg.
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C28

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         19

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

Schiff-base ligands have received a good deal of attention in biology and chemistry (Kahwa et al., 1986) in areas such as protein and enzyme mimics (Santos et al., 2001). Among the large number of compounds, 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one forms a variety of Schiff bases with aldehydes, and the synthesis and crystal structures of some of them, such as (E)-4-[(1,5-Dimethyl-3-oxo-2-phenyl-2,3- dihydro-1H-pyrazol-4-ylimino)methyl]-phenyl 4-chlorobenzoate (Han et al., 2007) and (E)-4-[4-(4-Chlorobenzyloxy)benzylideneamino]-1,5- dimethyl-2-phenyl-1H-pyrazol-3(2H)-one (Hu, 2006) have been reported. We now report the synthesis and molecular structure of the title Schiff base compound, (I), (Fig. 1)

The bond lengths and angles of (I) are within normal ranges (Allen et al., 1987). The pyrazolone ring (C16—C18/N1/N2/N3/O5) is nearly planar, with an r.m.s. deviation for fitted atoms of 0.030 Å. It makes a dihedral angle of 54.45 (9)° with the attached phenyl ring (C21—C26). The o-vanillin group (C8—C13/C15/O3/O4) is almost planar, with an r.m.s. deviation for fitted atoms of 0.020 Å. This group makes dihedral angles of 25.87 (4)°, 11.93 (3)° and 72.05 (7)°, with the the pyrazolone ring (C16—C18/N1/N2/N3/O5), the terminal C1—C6 benzene ring and the terminal C21—C26 phenyl ring, respectively.

The crystal packing is stabilized by weak intermolecular C10—H10···O2═S1 interaction (Table 1, Fig. 2) that form inversion dimers.

Related literature

For related structures, see: Han et al. (2007); Hu (2006). For general background, see: Kahwa et al. (1986); Santos et al. (2001). For reference structural data, see: Allen et al. (1987).

S2. Experimental

An anhydrous ethanol solution (50 ml) of 4-chloro-2-formyl-6-methoxyphenyl 4-methylbenzenesulfonate (3.41 g, 10 mmol) was added to an anhydrous ethanol solution (50 ml) of 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one (2.03 g, 10 mmol) and the mixture stirred at 350 K for 3 h under N₂, giving a yellow precipitate. The product was isolated, recrystallized from acetonitrile, and then dried in a vacuum to give pure compound (I) in 85% yield. Yellow blocks of (I) suitable for X-ray analysis were obtained by slow evaporation of an acetonitrile solution.

S3. Refinement

The H atoms were included in calculated positions (C—H = 0.93–0.96 Å) and refined as riding U_iso(H) = 1.2U_eq(C) or 1.5U_eq(methyl C).

Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures

	Fig. 1. The structure of (I), with displacement ellipsoids for non-H atoms drawn at the 30% probability level.
	Fig. 2. A packing diagram for (I), with hydrogen bonds drawn as dashed lines.

(E)-4-Chloro-2-[(2,3-dimethyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazol-4-yl)iminomethyl]-6-methoxyphenyl 4-methylbenzenesulfonate acetonitrile solvate

Crystal data

C26H24ClN3O5S·C2H3N	Z = 2
Mr = 567.06	F(000) = 592
Triclinic, P1	Dx = 1.349 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3242 (9) Å	Cell parameters from 4430 reflections
b = 13.2452 (17) Å	θ = 2.8–26.4°
c = 15.3145 (19) Å	µ = 0.26 mm^−1
α = 108.731 (2)°	T = 294 K
β = 93.303 (2)°	Block, yellow
γ = 94.910 (2)°	0.24 × 0.22 × 0.18 mm
V = 1396.1 (3) Å^3

Data collection

Bruker SMART APEX CCD diffractometer	4893 independent reflections
Radiation source: fine-focus sealed tube	4057 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.923, Tmax = 0.955	k = −15→13
7152 measured reflections	l = −18→14

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.133	w = 1/[σ^2(Fo^2) + (0.0722P)^2 + 0.7683P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
4893 reflections	Δρmax = 0.72 e Å^−3
358 parameters	Δρmin = −0.47 e Å^−3
19 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997a), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0160 (19)

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 > 2σ(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	0.62434 (8)	0.24085 (4)	0.38970 (4)	0.03804 (18)
Cl1	0.72326 (14)	−0.28513 (6)	0.33595 (5)	0.0783 (3)
O1	0.6098 (2)	0.25614 (14)	0.30172 (11)	0.0514 (4)
O2	0.4724 (2)	0.18514 (14)	0.41509 (12)	0.0509 (4)
O3	0.8015 (2)	0.17747 (11)	0.39394 (10)	0.0372 (4)
O4	0.7707 (2)	0.11000 (14)	0.53785 (10)	0.0505 (4)
O5	0.9284 (2)	0.18328 (12)	0.11286 (10)	0.0453 (4)
N1	0.7377 (2)	−0.03192 (14)	0.12557 (11)	0.0326 (4)
N2	0.8337 (2)	0.09923 (14)	−0.04314 (11)	0.0352 (4)
N3	0.7241 (2)	0.00446 (14)	−0.09482 (11)	0.0346 (4)
C1	0.6988 (3)	0.36377 (18)	0.47552 (15)	0.0405 (5)
C2	0.7231 (5)	0.3682 (2)	0.56658 (18)	0.0637 (8)
H2	0.7062	0.3062	0.5827	0.076*
C3	0.7733 (5)	0.4671 (2)	0.63347 (19)	0.0702 (8)
H3	0.7900	0.4711	0.6952	0.084*
C4	0.7994 (3)	0.5602 (2)	0.61129 (19)	0.0533 (6)
C5	0.7738 (4)	0.5527 (2)	0.52022 (19)	0.0559 (7)
H5	0.7901	0.6147	0.5042	0.067*
C6	0.7242 (4)	0.45531 (19)	0.45123 (17)	0.0494 (6)
H6	0.7082	0.4516	0.3896	0.059*
C7	0.8544 (4)	0.6671 (2)	0.6855 (2)	0.0747 (9)
H7A	0.9848	0.6758	0.7013	0.112*
H7B	0.7915	0.6699	0.7394	0.112*
H7C	0.8218	0.7236	0.6631	0.112*
C8	0.7729 (3)	0.06603 (17)	0.37770 (14)	0.0342 (5)
C9	0.7623 (3)	0.03145 (18)	0.45460 (14)	0.0386 (5)
C10	0.7456 (3)	−0.07720 (19)	0.44131 (15)	0.0438 (5)
H10	0.7382	−0.1023	0.4913	0.053*
C11	0.7400 (3)	−0.14827 (18)	0.35172 (16)	0.0445 (5)
C12	0.7497 (3)	−0.11512 (18)	0.27572 (15)	0.0392 (5)
H12	0.7457	−0.1652	0.2168	0.047*
C13	0.7657 (3)	−0.00529 (17)	0.28775 (14)	0.0338 (5)
C14	0.7599 (4)	0.0782 (2)	0.61864 (16)	0.0544 (6)
H14A	0.6451	0.0352	0.6139	0.082*
H14B	0.7678	0.1408	0.6727	0.082*
H14C	0.8597	0.0372	0.6234	0.082*
C15	0.7817 (3)	0.03317 (17)	0.20836 (13)	0.0332 (4)
H15	0.8235	0.1045	0.2179	0.040*
C16	0.7603 (3)	0.00425 (16)	0.05086 (13)	0.0306 (4)
C17	0.8511 (3)	0.10494 (17)	0.04996 (13)	0.0329 (4)
C18	0.6926 (3)	−0.05439 (16)	−0.03873 (13)	0.0318 (4)
C19	0.6029 (3)	−0.16592 (17)	−0.07583 (15)	0.0410 (5)
H19A	0.4963	−0.1690	−0.1165	0.062*
H19B	0.5665	−0.1893	−0.0256	0.062*
H19C	0.6877	−0.2119	−0.1095	0.062*
C20	0.7379 (3)	−0.0387 (2)	−0.19409 (14)	0.0458 (6)
H20A	0.8540	−0.0670	−0.2052	0.069*
H20B	0.7292	0.0173	−0.2208	0.069*
H20C	0.6398	−0.0950	−0.2217	0.069*
C21	0.8404 (3)	0.19099 (17)	−0.07269 (14)	0.0365 (5)
C22	0.6866 (3)	0.2147 (2)	−0.11566 (17)	0.0474 (6)
H22	0.5772	0.1695	−0.1279	0.057*
C23	0.6975 (4)	0.3068 (2)	−0.1402 (2)	0.0638 (8)
H23	0.5953	0.3229	−0.1701	0.077*
C24	0.8578 (5)	0.3746 (2)	−0.1208 (2)	0.0693 (8)
H24	0.8634	0.4370	−0.1365	0.083*
C25	1.0115 (4)	0.3500 (2)	−0.0779 (2)	0.0651 (8)
H25	1.1201	0.3961	−0.0648	0.078*
C26	1.0043 (3)	0.2575 (2)	−0.05454 (18)	0.0499 (6)
H26	1.1081	0.2401	−0.0270	0.060*
C27	0.7594 (6)	0.4169 (3)	0.1580 (3)	0.1074 (14)
H27A	0.8269	0.4824	0.1979	0.161*
H27B	0.8110	0.3952	0.0995	0.161*
H27C	0.7666	0.3619	0.1861	0.161*
C28	0.5735 (7)	0.4333 (3)	0.1443 (4)	0.128 (2)
N4	0.4221 (10)	0.4429 (5)	0.1437 (5)	0.186 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0442 (3)	0.0362 (3)	0.0308 (3)	−0.0002 (2)	−0.0012 (2)	0.0088 (2)
Cl1	0.1364 (8)	0.0419 (4)	0.0635 (5)	0.0086 (4)	0.0092 (4)	0.0272 (3)
O1	0.0684 (11)	0.0506 (10)	0.0334 (9)	0.0052 (8)	−0.0071 (7)	0.0135 (7)
O2	0.0449 (9)	0.0478 (10)	0.0571 (10)	−0.0033 (7)	0.0066 (8)	0.0148 (8)
O3	0.0424 (8)	0.0357 (8)	0.0318 (8)	−0.0017 (6)	0.0012 (6)	0.0105 (6)
O4	0.0740 (12)	0.0533 (10)	0.0236 (8)	0.0054 (8)	0.0044 (7)	0.0124 (7)
O5	0.0603 (10)	0.0392 (9)	0.0311 (8)	−0.0092 (7)	−0.0047 (7)	0.0095 (7)
N1	0.0352 (9)	0.0366 (9)	0.0270 (9)	0.0047 (7)	0.0025 (7)	0.0117 (7)
N2	0.0425 (10)	0.0353 (9)	0.0273 (9)	−0.0016 (7)	−0.0020 (7)	0.0120 (7)
N3	0.0436 (10)	0.0360 (9)	0.0228 (8)	0.0016 (8)	−0.0008 (7)	0.0089 (7)
C1	0.0443 (12)	0.0382 (12)	0.0340 (11)	0.0014 (9)	0.0008 (9)	0.0063 (9)
C2	0.102 (2)	0.0456 (15)	0.0395 (14)	−0.0013 (14)	−0.0023 (14)	0.0125 (12)
C3	0.103 (2)	0.0603 (18)	0.0353 (14)	0.0017 (16)	−0.0083 (14)	0.0029 (12)
C4	0.0465 (14)	0.0434 (14)	0.0578 (16)	0.0052 (11)	0.0011 (11)	0.0004 (12)
C5	0.0641 (17)	0.0380 (13)	0.0615 (17)	0.0027 (11)	0.0072 (13)	0.0111 (12)
C6	0.0612 (15)	0.0435 (13)	0.0434 (13)	0.0041 (11)	0.0049 (11)	0.0143 (11)
C7	0.074 (2)	0.0527 (17)	0.073 (2)	0.0020 (14)	−0.0036 (16)	−0.0105 (15)
C8	0.0371 (11)	0.0353 (11)	0.0302 (11)	0.0017 (9)	0.0008 (8)	0.0120 (9)
C9	0.0413 (12)	0.0490 (13)	0.0263 (11)	0.0025 (10)	0.0012 (9)	0.0143 (9)
C10	0.0525 (14)	0.0520 (14)	0.0342 (12)	0.0054 (11)	0.0042 (10)	0.0241 (10)
C11	0.0557 (14)	0.0384 (12)	0.0433 (13)	0.0037 (10)	0.0033 (10)	0.0194 (10)
C12	0.0489 (13)	0.0366 (11)	0.0314 (11)	0.0047 (9)	0.0015 (9)	0.0105 (9)
C13	0.0341 (10)	0.0404 (11)	0.0272 (10)	0.0011 (9)	0.0011 (8)	0.0125 (9)
C14	0.0636 (16)	0.0758 (18)	0.0277 (12)	0.0086 (13)	0.0048 (10)	0.0221 (12)
C15	0.0365 (11)	0.0351 (11)	0.0287 (10)	0.0033 (8)	0.0033 (8)	0.0115 (9)
C16	0.0350 (10)	0.0319 (10)	0.0252 (10)	0.0048 (8)	0.0025 (8)	0.0095 (8)
C17	0.0360 (11)	0.0367 (11)	0.0261 (10)	0.0040 (9)	0.0024 (8)	0.0105 (9)
C18	0.0333 (10)	0.0340 (11)	0.0282 (10)	0.0062 (8)	0.0041 (8)	0.0096 (8)
C19	0.0499 (13)	0.0365 (12)	0.0325 (11)	−0.0012 (10)	−0.0010 (9)	0.0079 (9)
C20	0.0576 (14)	0.0519 (14)	0.0235 (11)	−0.0006 (11)	0.0042 (9)	0.0080 (10)
C21	0.0460 (12)	0.0376 (11)	0.0284 (10)	0.0045 (9)	0.0054 (9)	0.0137 (9)
C22	0.0497 (13)	0.0488 (14)	0.0466 (14)	0.0025 (11)	−0.0028 (10)	0.0214 (11)
C23	0.0738 (19)	0.0610 (17)	0.0662 (18)	0.0118 (14)	−0.0092 (14)	0.0357 (15)
C24	0.088 (2)	0.0541 (17)	0.080 (2)	0.0037 (15)	0.0027 (17)	0.0433 (16)
C25	0.0662 (18)	0.0571 (17)	0.080 (2)	−0.0095 (14)	0.0029 (15)	0.0378 (15)
C26	0.0478 (14)	0.0514 (14)	0.0552 (15)	−0.0004 (11)	0.0029 (11)	0.0256 (12)
C27	0.116 (4)	0.075 (3)	0.134 (4)	0.009 (2)	0.029 (3)	0.036 (3)
C28	0.123 (4)	0.046 (2)	0.217 (6)	0.015 (2)	0.049 (4)	0.038 (3)
N4	0.185 (3)	0.183 (3)	0.190 (3)	0.0223 (11)	0.0167 (10)	0.0609 (12)

Geometric parameters (Å, º)

S1—O2	1.4240 (17)	C10—H10	0.9300
S1—O1	1.4247 (17)	C11—C12	1.373 (3)
S1—O3	1.6139 (16)	C12—C13	1.400 (3)
S1—C1	1.751 (2)	C12—H12	0.9300
Cl1—C11	1.743 (2)	C13—C15	1.468 (3)
O3—C8	1.411 (2)	C14—H14A	0.9600
O4—C9	1.356 (3)	C14—H14B	0.9600
O4—C14	1.434 (3)	C14—H14C	0.9600
O5—C17	1.233 (2)	C15—H15	0.9300
N1—C15	1.288 (3)	C16—C18	1.380 (3)
N1—C16	1.388 (3)	C16—C17	1.443 (3)
N2—C17	1.401 (3)	C18—C19	1.479 (3)
N2—N3	1.401 (2)	C19—H19A	0.9600
N2—C21	1.425 (3)	C19—H19B	0.9600
N3—C18	1.349 (3)	C19—H19C	0.9600
N3—C20	1.455 (3)	C20—H20A	0.9600
C1—C2	1.377 (3)	C20—H20B	0.9600
C1—C6	1.379 (3)	C20—H20C	0.9600
C2—C3	1.384 (4)	C21—C22	1.381 (3)
C2—H2	0.9300	C21—C26	1.385 (3)
C3—C4	1.381 (4)	C22—C23	1.385 (4)
C3—H3	0.9300	C22—H22	0.9300
C4—C5	1.367 (4)	C23—C24	1.372 (4)
C4—C7	1.509 (4)	C23—H23	0.9300
C5—C6	1.383 (3)	C24—C25	1.386 (4)
C5—H5	0.9300	C24—H24	0.9300
C6—H6	0.9300	C25—C26	1.380 (4)
C7—H7A	0.9600	C25—H25	0.9300
C7—H7B	0.9600	C26—H26	0.9300
C7—H7C	0.9600	C27—C28	1.411 (6)
C8—C13	1.393 (3)	C27—H27A	0.9600
C8—C9	1.398 (3)	C27—H27B	0.9600
C9—C10	1.381 (3)	C27—H27C	0.9600
C10—C11	1.388 (3)	C28—N4	1.126 (7)
O2—S1—O1	118.58 (11)	C12—C13—C15	120.92 (19)
O2—S1—O3	107.79 (9)	O4—C14—H14A	109.5
O1—S1—O3	107.52 (9)	O4—C14—H14B	109.5
O2—S1—C1	111.84 (11)	H14A—C14—H14B	109.5
O1—S1—C1	109.30 (11)	O4—C14—H14C	109.5
O3—S1—C1	100.09 (9)	H14A—C14—H14C	109.5
C8—O3—S1	118.42 (12)	H14B—C14—H14C	109.5
C9—O4—C14	117.70 (19)	N1—C15—C13	119.96 (19)
C15—N1—C16	119.45 (18)	N1—C15—H15	120.0
C17—N2—N3	109.06 (16)	C13—C15—H15	120.0
C17—N2—C21	123.68 (17)	C18—C16—N1	123.36 (18)
N3—N2—C21	120.39 (16)	C18—C16—C17	107.84 (17)
C18—N3—N2	107.95 (15)	N1—C16—C17	128.80 (17)
C18—N3—C20	125.35 (18)	O5—C17—N2	123.64 (19)
N2—N3—C20	118.97 (17)	O5—C17—C16	131.51 (19)
C2—C1—C6	121.1 (2)	N2—C17—C16	104.84 (16)
C2—C1—S1	119.46 (19)	N3—C18—C16	109.78 (18)
C6—C1—S1	119.36 (18)	N3—C18—C19	121.14 (18)
C1—C2—C3	118.3 (3)	C16—C18—C19	129.05 (19)
C1—C2—H2	120.9	C18—C19—H19A	109.5
C3—C2—H2	120.9	C18—C19—H19B	109.5
C4—C3—C2	122.0 (3)	H19A—C19—H19B	109.5
C4—C3—H3	119.0	C18—C19—H19C	109.5
C2—C3—H3	119.0	H19A—C19—H19C	109.5
C5—C4—C3	118.1 (2)	H19B—C19—H19C	109.5
C5—C4—C7	121.0 (3)	N3—C20—H20A	109.5
C3—C4—C7	120.9 (3)	N3—C20—H20B	109.5
C4—C5—C6	121.7 (3)	H20A—C20—H20B	109.5
C4—C5—H5	119.1	N3—C20—H20C	109.5
C6—C5—H5	119.1	H20A—C20—H20C	109.5
C1—C6—C5	118.8 (2)	H20B—C20—H20C	109.5
C1—C6—H6	120.6	C22—C21—C26	120.9 (2)
C5—C6—H6	120.6	C22—C21—N2	121.1 (2)
C4—C7—H7A	109.5	C26—C21—N2	117.9 (2)
C4—C7—H7B	109.5	C21—C22—C23	119.1 (2)
H7A—C7—H7B	109.5	C21—C22—H22	120.4
C4—C7—H7C	109.5	C23—C22—H22	120.4
H7A—C7—H7C	109.5	C24—C23—C22	120.5 (3)
H7B—C7—H7C	109.5	C24—C23—H23	119.7
C13—C8—C9	122.4 (2)	C22—C23—H23	119.7
C13—C8—O3	119.87 (18)	C23—C24—C25	119.9 (3)
C9—C8—O3	117.69 (18)	C23—C24—H24	120.0
O4—C9—C10	125.18 (19)	C25—C24—H24	120.0
O4—C9—C8	115.8 (2)	C26—C25—C24	120.3 (3)
C10—C9—C8	119.0 (2)	C26—C25—H25	119.8
C9—C10—C11	118.6 (2)	C24—C25—H25	119.8
C9—C10—H10	120.7	C25—C26—C21	119.1 (2)
C11—C10—H10	120.7	C25—C26—H26	120.5
C12—C11—C10	122.8 (2)	C21—C26—H26	120.5
C12—C11—Cl1	118.97 (18)	C28—C27—H27A	109.5
C10—C11—Cl1	118.23 (18)	C28—C27—H27B	109.5
C11—C12—C13	119.4 (2)	H27A—C27—H27B	109.5
C11—C12—H12	120.3	C28—C27—H27C	109.5
C13—C12—H12	120.3	H27A—C27—H27C	109.5
C8—C13—C12	117.77 (19)	H27B—C27—H27C	109.5
C8—C13—C15	121.27 (19)	N4—C28—C27	170.8 (7)
O2—S1—O3—C8	28.54 (16)	O3—C8—C13—C12	175.72 (18)
O1—S1—O3—C8	−100.38 (15)	C9—C8—C13—C15	−178.51 (19)
C1—S1—O3—C8	145.53 (15)	O3—C8—C13—C15	−1.9 (3)
C17—N2—N3—C18	−7.5 (2)	C11—C12—C13—C8	0.6 (3)
C21—N2—N3—C18	−159.44 (18)	C11—C12—C13—C15	178.3 (2)
C17—N2—N3—C20	−158.46 (19)	C16—N1—C15—C13	−177.41 (17)
C21—N2—N3—C20	49.6 (3)	C8—C13—C15—N1	−165.84 (19)
O2—S1—C1—C2	46.8 (2)	C12—C13—C15—N1	16.6 (3)
O1—S1—C1—C2	−179.9 (2)	C15—N1—C16—C18	−170.18 (19)
O3—S1—C1—C2	−67.1 (2)	C15—N1—C16—C17	8.9 (3)
O2—S1—C1—C6	−130.3 (2)	N3—N2—C17—O5	−174.35 (19)
O1—S1—C1—C6	3.0 (2)	C21—N2—C17—O5	−23.5 (3)
O3—S1—C1—C6	115.8 (2)	N3—N2—C17—C16	5.0 (2)
C6—C1—C2—C3	0.2 (4)	C21—N2—C17—C16	155.87 (19)
S1—C1—C2—C3	−176.9 (2)	C18—C16—C17—O5	178.4 (2)
C1—C2—C3—C4	−0.1 (5)	N1—C16—C17—O5	−0.8 (4)
C2—C3—C4—C5	0.2 (5)	C18—C16—C17—N2	−0.9 (2)
C2—C3—C4—C7	−179.9 (3)	N1—C16—C17—N2	179.94 (19)
C3—C4—C5—C6	−0.4 (4)	N2—N3—C18—C16	6.9 (2)
C7—C4—C5—C6	179.7 (3)	C20—N3—C18—C16	155.5 (2)
C2—C1—C6—C5	−0.4 (4)	N2—N3—C18—C19	−171.31 (18)
S1—C1—C6—C5	176.7 (2)	C20—N3—C18—C19	−22.7 (3)
C4—C5—C6—C1	0.5 (4)	N1—C16—C18—N3	175.48 (18)
S1—O3—C8—C13	88.5 (2)	C17—C16—C18—N3	−3.7 (2)
S1—O3—C8—C9	−94.75 (19)	N1—C16—C18—C19	−6.5 (3)
C14—O4—C9—C10	−0.6 (3)	C17—C16—C18—C19	174.3 (2)
C14—O4—C9—C8	179.9 (2)	C17—N2—C21—C22	−112.6 (2)
C13—C8—C9—O4	−179.84 (19)	N3—N2—C21—C22	35.1 (3)
O3—C8—C9—O4	3.5 (3)	C17—N2—C21—C26	65.5 (3)
C13—C8—C9—C10	0.6 (3)	N3—N2—C21—C26	−146.8 (2)
O3—C8—C9—C10	−176.11 (19)	C26—C21—C22—C23	−0.4 (4)
O4—C9—C10—C11	−179.5 (2)	N2—C21—C22—C23	177.7 (2)
C8—C9—C10—C11	0.0 (3)	C21—C22—C23—C24	−1.1 (4)
C9—C10—C11—C12	−0.3 (4)	C22—C23—C24—C25	1.2 (5)
C9—C10—C11—Cl1	178.83 (18)	C23—C24—C25—C26	0.0 (5)
C10—C11—C12—C13	−0.1 (4)	C24—C25—C26—C21	−1.4 (5)
Cl1—C11—C12—C13	−179.15 (17)	C22—C21—C26—C25	1.6 (4)
C9—C8—C13—C12	−0.9 (3)	N2—C21—C26—C25	−176.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2^i	0.93	2.57	3.386 (3)	146

Symmetry code: (i) −x+1, −y, −z+1.