7-Chloro-3-ethyl-10-phenyl-2-tosyl­pyrrolo[3,4-b]quinoline

The pyrrolidine ring of the title mol­ecule, C₂₆H₂₇ClN₂O₂S, adopts a twist conformation, while the tetra­hydro­pyridine ring is in a half-chair conformation. The tosyl group is attached to the pyrrolidine ring in a biaxial position. The pyrrolidine and tetra­hydro­pyridine rings are trans-fused. The pyridine-fused benzene ring forms dihedral angles of 73.95 (2) and 19.18 (5)°, respectively, with the benzene ring of the chloro­benzene and tosyl groups. The screw-related mol­ecules are linked into a chain along the [010] direction by N—H...O hydrogen bonds, and the chains are cross-linked into a three-dimensional network by C—H...π inter­actions and weak π–π inter­actions [centroid–centroid distance = 3.7488 (5) Å].

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.001 Å
• R factor = 0.039
• wR factor = 0.108
• Data-to-parameter ratio = 48.9

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.780     0.897
            Tmin(prime) and Tmax expected:      0.866     0.894
            RR(prime) =      0.897
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.89
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.71 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.31 Ratio
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C2     .....          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C3     .....          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C10    .....          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C11    .....          S

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 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

Pyrrolo[3,4-b]quinoline derivatives exhibit cytotoxic (Xiao et al., 2006), antibacterial (Fujita et al., 1996) and interferon inducing activities (Crenshaw et al., 1976). They are also found to bind benzodiazepine receptors (Anzini et al., 1990, 1992). Previously, we have reported the crystal structure of a pyrrolo[3,4-b]quinoline derivative (Sudha et al., 2007). We report herein the crystal structure of the title pyrroloquinoline derivative, (I), Fig. 1.

Bond lengths and angles show normal values (Allen et al., 1987), and are comparable with those in a related structure (Sudha et al., 2007). As a result of the repulsive interaction between the short S═O bonds, atom S1 has a distorted tetrahedral configuration, with the O2—S1—O1 [119.63 (4)°] angle deviating significantly from ideal tetrahedral value.

The pyrrolidine ring has a twist conformation, with the local twofold rotation axis passes through atom N1 and the midpoint of the bond C2—C10. The relevant asymmetry parameters ΔC₂[C2—C10] (Duax et al., 1976) and the puckering parameters q₂ and ϕ (Cremer & Pople, 1975) are 0.24 (7)°, 0.4686 (8) Å and 90.05 (9)°, respectively. The tosyl group is attached to the pyrrolidine ring in a biaxial position.

The tetrahydropyridine ring adopts a half-chair conformation with a local twofold rotation axis passing through the midpoints of the C4—C9 and C2—C10 bonds; the puckering (Q, θ, ϕ) and asymmetry (ΔC₂[C4—C9]) parameters are 0.4744 (8) Å, 133.81 (10)°, 89.08 (13)° and 2.29 (10)°, respectively. The pyrrolidine and tetrahydropyridine rings are trans-fused. The C19—C24 phenyl ring forms dihedral angles of 73.95 (2) and 19.18 (5)°, respectively, with the C4—C9 and C12—C17 benzene rings.

The screw-related molecules are linked into a chain along the [0 1 0] direction by N—H···O hydrogen bonds. The chains are cross-linked into a three-dimensional network (Fig.2) by C—H···π interactions involving the C3—H3 group and the C4—C9 benzene ring (centroid Cg1) of the molecule at (-x, 1 - y, -z), and π-π interactions between the C12—C17 benzene rings of molecules at (x, y, z) and (1 - x, 1 - y, 1 - z) [centroid-centroid distance is 3.7488 (5) Å].

Related literature

For general background, see: Anzini et al. (1990, 1992); Crenshaw et al. (1976); Fujita et al. (1996); Xiao et al. (2006). For a related structure, see: Sudha et al. (2007). For ring-puckering parameters, see: Cremer & Pople (1975). For asymmetry parameters, see: Duax et al. (1976). For bond-length data, see: Allen et al. (1987).

S2. Experimental

InCl₃ (20 mol%) was added to a mixture of 2-(N-cinnamyl-N-tosylamino)butanal (1 mmol) and arylamine (1 mmol) in acetonitrile (2o ml). The reaction mixture was stirred at room temperature for 30 min. On completion of the reaction, as indicated by TLC, the mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine and dried over Na₂SO₄. The solvent was evaporated in vacuo and the crude product was chromatographed using a hexane-ethyl acetate (8.5:1.5 v/v) mixture to obtain the title compound. The compound was recrystallized from ethyl acetate solution by slow evaporation.

S3. Refinement

The N-bound H atom was located from a difference map and refined freely with an isotropic displacement parameter. The remaining H atoms were positioned geometrically (C—H = 0.93–0.98 Å) and allowed to ride on their parent atoms, with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(C_methyl). A rotating group model was used for the methyl groups attached to aromatic rings.

Computing details

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

Figures

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 80% probability level.
	Fig. 2. Part of the three-dimensional network in the title compound. Dashed and dotted lines indicate N—H···O and C—H···π interactions, respectively. The π-π interaction is shown by a dashed open line. For the sake of clarity, H atoms not involved in the interactions have been omitted.

7-Chloro-3-ethyl-10-phenyl-2-tosylpyrrolo[3,4-b]quinoline

Crystal data

C26H27ClN2O2S	F(000) = 984
Mr = 467.01	Dx = 1.336 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9717 reflections
a = 9.5843 (2) Å	θ = 2.4–41.9°
b = 13.2007 (2) Å	µ = 0.28 mm^−1
c = 20.3414 (3) Å	T = 100 K
β = 115.550 (1)°	Block, colourless
V = 2321.91 (7) Å^3	0.50 × 0.41 × 0.40 mm
Z = 4

Data collection

Bruker SMART APEXII CCD area-detector diffractometer	14373 independent reflections
Radiation source: fine-focus sealed tube	11857 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
Detector resolution: 8.33 pixels mm^-1	θmax = 40.0°, θmin = 2.2°
ω scans	h = −17→17
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −23→23
Tmin = 0.780, Tmax = 0.897	l = −36→36
115565 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0546P)^2 + 0.4777P] where P = (Fo^2 + 2Fc^2)/3
14373 reflections	(Δ/σ)max = 0.001
294 parameters	Δρmax = 0.61 e Å^−3
0 restraints	Δρmin = −0.42 e Å^−3

Special details

Experimental. The low-temparture data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
Cl1	−0.46322 (2)	0.604543 (14)	−0.054121 (10)	0.01947 (4)
S1	0.61137 (2)	0.510831 (13)	0.338265 (10)	0.01478 (4)
O1	0.66669 (7)	0.40806 (4)	0.35158 (3)	0.02040 (10)
O2	0.72013 (7)	0.59313 (4)	0.36178 (3)	0.01988 (10)
N1	0.51131 (7)	0.52196 (4)	0.25005 (3)	0.01442 (9)
N2	0.20015 (7)	0.68671 (4)	0.12988 (4)	0.01623 (10)
H1N2	0.2303 (16)	0.7428 (10)	0.1229 (8)	0.028 (3)*
C1	0.37966 (8)	0.44894 (5)	0.21613 (4)	0.01491 (10)
H1A	0.3709	0.4054	0.2526	0.018*
H1B	0.3917	0.4073	0.1796	0.018*
C2	0.24059 (8)	0.51861 (5)	0.18181 (4)	0.01314 (10)
H2	0.2183	0.5463	0.2210	0.016*
C3	0.09024 (8)	0.47624 (5)	0.12322 (4)	0.01293 (10)
H3	0.1152	0.4373	0.0887	0.016*
C4	−0.01388 (8)	0.56469 (5)	0.08214 (4)	0.01342 (10)
C5	−0.17147 (8)	0.54847 (5)	0.03904 (4)	0.01475 (10)
H5	−0.2130	0.4843	0.0371	0.018*
C6	−0.26683 (8)	0.62687 (5)	−0.00093 (4)	0.01552 (10)
C7	−0.20779 (9)	0.72344 (5)	0.00073 (4)	0.01768 (11)
H7	−0.2718	0.7755	−0.0268	0.021*
C8	−0.05244 (9)	0.74104 (5)	0.04386 (4)	0.01753 (11)
H8	−0.0128	0.8058	0.0455	0.021*
C9	0.04660 (8)	0.66348 (5)	0.08514 (4)	0.01436 (10)
C10	0.30748 (8)	0.60324 (5)	0.15364 (4)	0.01342 (10)
H10	0.3284	0.5787	0.1133	0.016*
C11	0.45891 (8)	0.62662 (5)	0.21984 (4)	0.01418 (10)
H11	0.4354	0.6651	0.2550	0.017*
C12	0.48094 (8)	0.52634 (5)	0.37754 (4)	0.01599 (11)
C13	0.44059 (9)	0.62360 (6)	0.39012 (4)	0.01736 (11)
H13	0.4866	0.6801	0.3804	0.021*
C14	0.33104 (9)	0.63518 (6)	0.41731 (4)	0.02117 (13)
H14	0.3060	0.6999	0.4268	0.025*
C15	0.25807 (10)	0.55165 (7)	0.43055 (5)	0.02340 (14)
C16	0.30038 (11)	0.45522 (7)	0.41780 (5)	0.02539 (15)
H16	0.2529	0.3988	0.4266	0.030*
C17	0.41188 (10)	0.44177 (6)	0.39219 (5)	0.02144 (13)
H17	0.4403	0.3769	0.3849	0.026*
C18	0.13611 (13)	0.56452 (10)	0.45801 (6)	0.0352 (2)
H18A	0.1420	0.6317	0.4770	0.053*
H18B	0.1529	0.5160	0.4958	0.053*
H18C	0.0357	0.5540	0.4187	0.053*
C19	0.02137 (8)	0.40411 (5)	0.15955 (4)	0.01436 (10)
C20	−0.05309 (10)	0.44085 (6)	0.20051 (5)	0.02128 (13)
H20	−0.0713	0.5100	0.2011	0.026*
C21	−0.10042 (12)	0.37489 (8)	0.24045 (5)	0.02782 (17)
H21	−0.1509	0.4000	0.2671	0.033*
C22	−0.07219 (11)	0.27164 (7)	0.24043 (5)	0.02752 (17)
H22	−0.1026	0.2276	0.2675	0.033*
C23	0.00145 (10)	0.23441 (6)	0.19981 (5)	0.02406 (15)
H23	0.0206	0.1653	0.1998	0.029*
C24	0.04692 (9)	0.30017 (5)	0.15897 (4)	0.01788 (12)
H24	0.0946	0.2745	0.1312	0.021*
C25	0.57811 (9)	0.68532 (5)	0.20407 (4)	0.01726 (11)
H25A	0.5364	0.7520	0.1863	0.021*
H25B	0.6696	0.6946	0.2496	0.021*
C26	0.62696 (10)	0.63715 (7)	0.14935 (5)	0.02466 (15)
H26A	0.7018	0.6797	0.1432	0.037*
H26B	0.5382	0.6295	0.1034	0.037*
H26C	0.6717	0.5719	0.1669	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.01587 (7)	0.02092 (8)	0.01830 (8)	0.00043 (5)	0.00424 (6)	0.00035 (5)
S1	0.01325 (7)	0.01446 (7)	0.01487 (7)	0.00160 (5)	0.00440 (6)	0.00037 (5)
O1	0.0208 (3)	0.0166 (2)	0.0214 (3)	0.00656 (18)	0.0068 (2)	0.00265 (18)
O2	0.0148 (2)	0.0208 (2)	0.0205 (3)	−0.00274 (17)	0.00431 (19)	−0.00168 (18)
N1	0.0147 (2)	0.0130 (2)	0.0143 (2)	−0.00002 (16)	0.00514 (19)	0.00044 (17)
N2	0.0149 (2)	0.0112 (2)	0.0212 (3)	0.00013 (17)	0.0065 (2)	0.00268 (18)
C1	0.0153 (3)	0.0122 (2)	0.0156 (3)	0.00003 (18)	0.0051 (2)	0.00010 (19)
C2	0.0144 (2)	0.0116 (2)	0.0139 (3)	−0.00003 (17)	0.0066 (2)	0.00053 (18)
C3	0.0144 (2)	0.0116 (2)	0.0138 (3)	0.00027 (17)	0.0069 (2)	0.00067 (17)
C4	0.0153 (2)	0.0124 (2)	0.0134 (3)	0.00074 (18)	0.0070 (2)	0.00097 (18)
C5	0.0157 (3)	0.0143 (2)	0.0140 (3)	0.00022 (19)	0.0061 (2)	0.00023 (19)
C6	0.0151 (3)	0.0168 (3)	0.0140 (3)	0.0015 (2)	0.0057 (2)	0.00011 (19)
C7	0.0176 (3)	0.0153 (3)	0.0186 (3)	0.0028 (2)	0.0064 (2)	0.0023 (2)
C8	0.0179 (3)	0.0130 (2)	0.0207 (3)	0.0017 (2)	0.0074 (2)	0.0030 (2)
C9	0.0152 (3)	0.0128 (2)	0.0155 (3)	0.00094 (18)	0.0070 (2)	0.00149 (19)
C10	0.0138 (2)	0.0120 (2)	0.0150 (3)	0.00031 (17)	0.0067 (2)	0.00106 (18)
C11	0.0155 (3)	0.0119 (2)	0.0153 (3)	0.00014 (18)	0.0068 (2)	−0.00002 (18)
C12	0.0169 (3)	0.0163 (3)	0.0139 (3)	0.0006 (2)	0.0057 (2)	−0.00019 (19)
C13	0.0165 (3)	0.0177 (3)	0.0160 (3)	0.0007 (2)	0.0053 (2)	−0.0019 (2)
C14	0.0194 (3)	0.0259 (3)	0.0173 (3)	0.0043 (2)	0.0071 (3)	−0.0017 (2)
C15	0.0203 (3)	0.0348 (4)	0.0162 (3)	0.0023 (3)	0.0088 (3)	0.0020 (3)
C16	0.0287 (4)	0.0283 (4)	0.0234 (4)	−0.0031 (3)	0.0153 (3)	0.0034 (3)
C17	0.0277 (4)	0.0185 (3)	0.0206 (3)	−0.0011 (2)	0.0128 (3)	0.0013 (2)
C18	0.0286 (4)	0.0551 (6)	0.0287 (5)	0.0069 (4)	0.0188 (4)	0.0065 (4)
C19	0.0141 (2)	0.0144 (2)	0.0146 (3)	−0.00066 (18)	0.0062 (2)	0.00182 (19)
C20	0.0241 (3)	0.0225 (3)	0.0228 (3)	0.0006 (2)	0.0153 (3)	0.0021 (2)
C21	0.0289 (4)	0.0359 (4)	0.0258 (4)	−0.0038 (3)	0.0185 (4)	0.0036 (3)
C22	0.0257 (4)	0.0325 (4)	0.0236 (4)	−0.0088 (3)	0.0098 (3)	0.0085 (3)
C23	0.0238 (4)	0.0187 (3)	0.0255 (4)	−0.0052 (2)	0.0066 (3)	0.0064 (3)
C24	0.0181 (3)	0.0143 (2)	0.0198 (3)	−0.0016 (2)	0.0068 (2)	0.0021 (2)
C25	0.0173 (3)	0.0151 (3)	0.0194 (3)	−0.0031 (2)	0.0079 (2)	−0.0008 (2)
C26	0.0233 (4)	0.0272 (4)	0.0296 (4)	−0.0060 (3)	0.0172 (3)	−0.0048 (3)

Geometric parameters (Å, º)

Cl1—C6	1.7447 (7)	C12—C17	1.3941 (11)
S1—O2	1.4373 (6)	C12—C13	1.3959 (10)
S1—O1	1.4392 (6)	C13—C14	1.3902 (11)
S1—N1	1.6360 (6)	C13—H13	0.93
S1—C12	1.7619 (7)	C14—C15	1.3928 (13)
N1—C1	1.4988 (9)	C14—H14	0.93
N1—C11	1.5075 (9)	C15—C16	1.3938 (13)
N2—C9	1.3902 (9)	C15—C18	1.5069 (12)
N2—C10	1.4412 (9)	C16—C17	1.3875 (12)
N2—H1N2	0.830 (14)	C16—H16	0.93
C1—C2	1.5189 (9)	C17—H17	0.93
C1—H1A	0.97	C18—H18A	0.96
C1—H1B	0.97	C18—H18B	0.96
C2—C10	1.5179 (9)	C18—H18C	0.96
C2—C3	1.5258 (10)	C19—C24	1.3947 (10)
C2—H2	0.98	C19—C20	1.3970 (10)
C3—C19	1.5196 (9)	C20—C21	1.3936 (11)
C3—C4	1.5291 (9)	C20—H20	0.93
C3—H3	0.98	C21—C22	1.3896 (14)
C4—C5	1.3977 (10)	C21—H21	0.93
C4—C9	1.4177 (9)	C22—C23	1.3875 (14)
C5—C6	1.3881 (10)	C22—H22	0.93
C5—H5	0.93	C23—C24	1.3950 (11)
C6—C7	1.3892 (10)	C23—H23	0.93
C7—C8	1.3833 (11)	C24—H24	0.93
C7—H7	0.93	C25—C26	1.5205 (11)
C8—C9	1.4025 (10)	C25—H25A	0.97
C8—H8	0.93	C25—H25B	0.97
C10—C11	1.5262 (10)	C26—H26A	0.96
C10—H10	0.98	C26—H26B	0.96
C11—C25	1.5247 (9)	C26—H26C	0.96
C11—H11	0.98
O2—S1—O1	119.63 (4)	N1—C11—H11	108.6
O2—S1—N1	107.16 (3)	C25—C11—H11	108.6
O1—S1—N1	106.57 (3)	C10—C11—H11	108.6
O2—S1—C12	108.41 (4)	C17—C12—C13	120.18 (7)
O1—S1—C12	107.47 (4)	C17—C12—S1	119.93 (6)
N1—S1—C12	106.98 (3)	C13—C12—S1	119.79 (5)
C1—N1—C11	109.60 (5)	C14—C13—C12	119.38 (7)
C1—N1—S1	115.22 (5)	C14—C13—H13	120.3
C11—N1—S1	117.65 (5)	C12—C13—H13	120.3
C9—N2—C10	116.86 (6)	C13—C14—C15	121.21 (7)
C9—N2—H1N2	115.7 (10)	C13—C14—H14	119.4
C10—N2—H1N2	119.3 (10)	C15—C14—H14	119.4
N1—C1—C2	102.70 (5)	C14—C15—C16	118.45 (7)
N1—C1—H1A	111.2	C14—C15—C18	121.13 (9)
C2—C1—H1A	111.2	C16—C15—C18	120.42 (9)
N1—C1—H1B	111.2	C17—C16—C15	121.31 (8)
C2—C1—H1B	111.2	C17—C16—H16	119.3
H1A—C1—H1B	109.1	C15—C16—H16	119.3
C10—C2—C1	100.92 (5)	C16—C17—C12	119.43 (8)
C10—C2—C3	112.66 (6)	C16—C17—H17	120.3
C1—C2—C3	118.88 (5)	C12—C17—H17	120.3
C10—C2—H2	107.9	C15—C18—H18A	109.5
C1—C2—H2	107.9	C15—C18—H18B	109.5
C3—C2—H2	107.9	H18A—C18—H18B	109.5
C19—C3—C2	108.17 (5)	C15—C18—H18C	109.5
C19—C3—C4	115.23 (5)	H18A—C18—H18C	109.5
C2—C3—C4	108.71 (5)	H18B—C18—H18C	109.5
C19—C3—H3	108.2	C24—C19—C20	118.91 (6)
C2—C3—H3	108.2	C24—C19—C3	119.84 (6)
C4—C3—H3	108.2	C20—C19—C3	120.88 (6)
C5—C4—C9	118.63 (6)	C21—C20—C19	120.61 (8)
C5—C4—C3	119.98 (6)	C21—C20—H20	119.7
C9—C4—C3	121.37 (6)	C19—C20—H20	119.7
C6—C5—C4	120.90 (6)	C22—C21—C20	120.01 (8)
C6—C5—H5	119.5	C22—C21—H21	120.0
C4—C5—H5	119.5	C20—C21—H21	120.0
C5—C6—C7	120.77 (7)	C23—C22—C21	119.79 (7)
C5—C6—Cl1	119.93 (5)	C23—C22—H22	120.1
C7—C6—Cl1	119.30 (6)	C21—C22—H22	120.1
C8—C7—C6	119.03 (7)	C22—C23—C24	120.27 (8)
C8—C7—H7	120.5	C22—C23—H23	119.9
C6—C7—H7	120.5	C24—C23—H23	119.9
C7—C8—C9	121.50 (6)	C19—C24—C23	120.40 (7)
C7—C8—H8	119.2	C19—C24—H24	119.8
C9—C8—H8	119.2	C23—C24—H24	119.8
N2—C9—C8	118.88 (6)	C26—C25—C11	115.89 (6)
N2—C9—C4	121.93 (6)	C26—C25—H25A	108.3
C8—C9—C4	119.15 (6)	C11—C25—H25A	108.3
N2—C10—C2	109.44 (5)	C26—C25—H25B	108.3
N2—C10—C11	114.26 (5)	C11—C25—H25B	108.3
C2—C10—C11	102.21 (5)	H25A—C25—H25B	107.4
N2—C10—H10	110.2	C25—C26—H26A	109.5
C2—C10—H10	110.2	C25—C26—H26B	109.5
C11—C10—H10	110.2	H26A—C26—H26B	109.5
N1—C11—C25	113.80 (6)	C25—C26—H26C	109.5
N1—C11—C10	101.37 (5)	H26A—C26—H26C	109.5
C25—C11—C10	115.53 (6)	H26B—C26—H26C	109.5
O2—S1—N1—C1	−173.83 (5)	C1—N1—C11—C25	−139.26 (6)
O1—S1—N1—C1	56.99 (6)	S1—N1—C11—C25	86.54 (7)
C12—S1—N1—C1	−57.73 (5)	C1—N1—C11—C10	−14.57 (7)
O2—S1—N1—C11	−42.12 (6)	S1—N1—C11—C10	−148.77 (5)
O1—S1—N1—C11	−171.30 (5)	N2—C10—C11—N1	156.64 (5)
C12—S1—N1—C11	73.98 (5)	C2—C10—C11—N1	38.54 (6)
C11—N1—C1—C2	−14.91 (7)	N2—C10—C11—C25	−79.85 (7)
S1—N1—C1—C2	120.50 (5)	C2—C10—C11—C25	162.05 (5)
N1—C1—C2—C10	38.47 (6)	O2—S1—C12—C17	−151.08 (7)
N1—C1—C2—C3	162.15 (5)	O1—S1—C12—C17	−20.46 (8)
C10—C2—C3—C19	−171.57 (5)	N1—S1—C12—C17	93.66 (7)
C1—C2—C3—C19	70.74 (7)	O2—S1—C12—C13	32.48 (7)
C10—C2—C3—C4	−45.78 (7)	O1—S1—C12—C13	163.10 (6)
C1—C2—C3—C4	−163.48 (5)	N1—S1—C12—C13	−82.78 (7)
C19—C3—C4—C5	−41.97 (9)	C17—C12—C13—C14	−0.03 (11)
C2—C3—C4—C5	−163.54 (6)	S1—C12—C13—C14	176.40 (6)
C19—C3—C4—C9	139.68 (6)	C12—C13—C14—C15	−1.58 (12)
C2—C3—C4—C9	18.11 (8)	C13—C14—C15—C16	1.74 (13)
C9—C4—C5—C6	0.93 (10)	C13—C14—C15—C18	−178.26 (8)
C3—C4—C5—C6	−177.46 (6)	C14—C15—C16—C17	−0.31 (14)
C4—C5—C6—C7	0.21 (10)	C18—C15—C16—C17	179.69 (9)
C4—C5—C6—Cl1	−179.86 (5)	C15—C16—C17—C12	−1.26 (14)
C5—C6—C7—C8	−1.04 (11)	C13—C12—C17—C16	1.43 (12)
Cl1—C6—C7—C8	179.03 (6)	S1—C12—C17—C16	−175.00 (7)
C6—C7—C8—C9	0.72 (11)	C2—C3—C19—C24	−97.10 (8)
C10—N2—C9—C8	−161.70 (6)	C4—C3—C19—C24	141.03 (7)
C10—N2—C9—C4	20.69 (10)	C2—C3—C19—C20	75.81 (8)
C7—C8—C9—N2	−177.26 (7)	C4—C3—C19—C20	−46.05 (9)
C7—C8—C9—C4	0.42 (11)	C24—C19—C20—C21	0.33 (13)
C5—C4—C9—N2	176.37 (6)	C3—C19—C20—C21	−172.66 (8)
C3—C4—C9—N2	−5.25 (10)	C19—C20—C21—C22	0.70 (15)
C5—C4—C9—C8	−1.23 (10)	C20—C21—C22—C23	−0.80 (15)
C3—C4—C9—C8	177.14 (6)	C21—C22—C23—C24	−0.12 (14)
C9—N2—C10—C2	−47.74 (8)	C20—C19—C24—C23	−1.24 (12)
C9—N2—C10—C11	−161.64 (6)	C3—C19—C24—C23	171.81 (7)
C1—C2—C10—N2	−170.03 (6)	C22—C23—C24—C19	1.15 (13)
C3—C2—C10—N2	62.12 (7)	N1—C11—C25—C26	59.76 (9)
C1—C2—C10—C11	−48.55 (6)	C10—C11—C25—C26	−56.95 (9)
C3—C2—C10—C11	−176.40 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1^i	0.829 (14)	2.358 (14)	3.1454 (8)	159 (2)
C25—H25B···O2	0.97	2.51	3.1399 (9)	123
C3—H3···Cg1^ii	0.98	2.85	3.7962 (8)	163

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