4-(2-Chloro­phenyl)-3-(2,6-di­chloro­phenyl)­spiro­isoxazoline-5,2'-benzo­[4,5]­imidazo­[2,1-b]­thia­zol-3'-one dioxane hemisolvate

The title compound, C₂₃H₁₂Cl₃N₃O₂S·0.5C₄H₈O₂, was synthesized by the intermolecular [3+2]-cyclo­addition of 2,6-di­chloro­benzo­nitrile oxide and 2-(2-chloro­benzyl­idene)­benzo­[4,5]­imidazo­[2,1-b]­thia­zol-3-one. The dioxane mol­ecule of solvation is located about a centre of inversion. A spiro junction links an isoxazoline ring and a planar benzo­[4,5]­imidazo­[2,1-b]­thia­zol-3-one ring.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.049
• wR factor = 0.142
• Data-to-parameter ratio = 12.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

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

4-(2-Chlorophenyl)-3-(2,6-dichlorophenyl)spiroisoxazoline-5,2'- benzo[4,5]imidazo[2,1-b]thiazol-3'-one dioxane hemisolvate

Crystal data

C23H12Cl3N3O2S·0.5C4H8O2	Z = 2
Mr = 544.82	F(000) = 556
Triclinic, P1	Dx = 1.517 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.904 (2) Å	Cell parameters from 881 reflections
b = 9.166 (3) Å	θ = 3.4–26.1°
c = 16.963 (5) Å	µ = 0.51 mm^−1
α = 102.180 (5)°	T = 293 K
β = 93.697 (5)°	Plate, colorless
γ = 94.789 (5)°	0.24 × 0.22 × 0.08 mm
V = 1192.8 (6) Å^3

Data collection

Bruker CCD area-detector diffractometer	4851 independent reflections
Radiation source: fine-focus sealed tube	3444 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 26.4°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 1977; Blessing, 1995)	h = −9→8
Tmin = 0.862, Tmax = 1	k = −11→11
9829 measured reflections	l = −21→21

Refinement

Refinement on F^2	393 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.049	w = 1/[σ^2(Fo^2) + (0.084P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.142	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.68 e Å^−3
4851 reflections	Δρmin = −0.56 e Å^−3
377 parameters

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	Occ. (<1)
Cl1	0.38077 (11)	0.91018 (14)	0.29875 (6)	0.0832 (3)
Cl2	0.83875 (17)	0.71861 (17)	0.49453 (6)	0.1089 (5)
N1	0.8408 (2)	0.8194 (2)	0.08151 (12)	0.0323 (5)
N2	1.0163 (3)	0.6835 (2)	0.00365 (13)	0.0396 (5)
N3	0.8464 (3)	0.9097 (3)	0.34566 (13)	0.0431 (5)
O1	0.6529 (3)	0.9299 (2)	0.16666 (12)	0.0530 (5)
O2	0.9404 (2)	0.8821 (2)	0.27602 (11)	0.0424 (4)
S1	0.99205 (9)	0.64363 (8)	0.15980 (4)	0.0434 (2)
C1	0.8229 (3)	0.8615 (3)	0.00660 (15)	0.0332 (5)
C2	0.7263 (3)	0.9613 (3)	−0.02185 (17)	0.0416 (6)
H2	0.6536	1.0177	0.0102	0.050*
C3	0.7444 (4)	0.9721 (3)	−0.10107 (17)	0.0468 (7)
H3	0.6806	1.0367	−0.1232	0.056*
C4	0.8544 (4)	0.8898 (3)	−0.14832 (17)	0.0491 (7)
H4	0.8635	0.9014	−0.2011	0.059*
C5	0.9510 (4)	0.7907 (3)	−0.11920 (16)	0.0441 (6)
H5	1.0252	0.7360	−0.1512	0.053*
C6	0.9329 (3)	0.7762 (3)	−0.04036 (15)	0.0353 (6)
C7	0.9573 (3)	0.7144 (3)	0.07330 (15)	0.0344 (6)
C8	0.7631 (3)	0.8486 (3)	0.15246 (15)	0.0351 (6)
C9	0.8450 (3)	0.7655 (3)	0.21364 (15)	0.0352 (6)
C11	0.7206 (3)	0.8091 (3)	0.33621 (15)	0.0370 (6)
C12	0.5975 (4)	0.8057 (3)	0.39834 (16)	0.0460 (7)
C13	0.4322 (4)	0.8440 (4)	0.38491 (19)	0.0592 (8)
C14	0.3093 (5)	0.8360 (5)	0.4380 (2)	0.0788 (11)
H14	0.2010	0.8638	0.4276	0.095*
C15	0.3504 (7)	0.7860 (6)	0.5064 (3)	0.0978 (14)
H15	0.2678	0.7773	0.5423	0.117*
C16	0.5111 (7)	0.7484 (5)	0.5233 (2)	0.0958 (15)
H16	0.5372	0.7150	0.5704	0.115*
C17	0.6347 (5)	0.7607 (4)	0.46985 (19)	0.0660 (9)
C10	0.7186 (18)	0.6861 (10)	0.2608 (6)	0.038 (3)	0.550 (17)
H10	0.6050	0.6677	0.2317	0.045*	0.550 (17)
Cl3	0.4488 (10)	0.4153 (9)	0.2449 (3)	0.0915 (15)	0.550 (17)
C18	0.7767 (14)	0.5397 (9)	0.2776 (8)	0.042 (2)	0.550 (17)
C19	0.6621 (14)	0.4151 (10)	0.2732 (6)	0.0553 (19)	0.550 (17)
C20	0.7190 (18)	0.2826 (11)	0.2910 (9)	0.068 (3)	0.550 (17)
H20	0.6439	0.1962	0.2838	0.082*	0.550 (17)
C21	0.8837 (18)	0.2821 (11)	0.3186 (6)	0.068 (2)	0.550 (17)
H21	0.9208	0.1944	0.3297	0.082*	0.550 (17)
C22	0.9964 (17)	0.4079 (11)	0.3304 (8)	0.066 (2)	0.550 (17)
H22	1.1077	0.4071	0.3516	0.079*	0.550 (17)
C23	0.9432 (16)	0.5352 (12)	0.3105 (9)	0.0521 (19)	0.550 (17)
H23	1.0196	0.6210	0.3191	0.063*	0.550 (17)
C10'	0.705 (2)	0.6954 (10)	0.2567 (7)	0.034 (4)	0.450 (17)
H10'	0.5926	0.6933	0.2278	0.040*	0.450 (17)
Cl3'	0.3888 (10)	0.4640 (9)	0.2337 (4)	0.0807 (17)	0.450 (17)
C18'	0.7270 (13)	0.5444 (7)	0.2784 (9)	0.036 (2)	0.450 (17)
C19'	0.5944 (14)	0.4299 (8)	0.2608 (7)	0.050 (2)	0.450 (17)
C20'	0.6229 (19)	0.2867 (7)	0.2702 (6)	0.072 (3)	0.450 (17)
H20'	0.5342	0.2101	0.2584	0.087*	0.450 (17)
C21'	0.784 (2)	0.2580 (9)	0.2973 (7)	0.073 (4)	0.450 (17)
H21'	0.8030	0.1622	0.3037	0.087*	0.450 (17)
C22'	0.9165 (18)	0.3725 (13)	0.3150 (8)	0.066 (3)	0.450 (17)
H22'	1.0242	0.3533	0.3331	0.080*	0.450 (17)
C23'	0.8880 (14)	0.5157 (11)	0.3055 (9)	0.050 (3)	0.450 (17)
H23'	0.9767	0.5923	0.3173	0.060*	0.450 (17)
C24	0.4068 (4)	0.6003 (4)	0.04687 (19)	0.0549 (8)
H24A	0.3875	0.7024	0.0715	0.066*
H24B	0.3150	0.5336	0.0590	0.066*
C25	0.5939 (4)	0.4169 (3)	0.04301 (18)	0.0516 (7)
H25A	0.5054	0.3471	0.0552	0.062*
H25B	0.7027	0.3936	0.0645	0.062*
O3	0.5655 (2)	0.5663 (2)	0.08013 (12)	0.0495 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0527 (5)	0.1400 (9)	0.0673 (6)	0.0269 (6)	0.0095 (4)	0.0373 (6)
Cl2	0.1214 (10)	0.1710 (13)	0.0550 (6)	0.0612 (9)	0.0111 (6)	0.0518 (7)
N1	0.0295 (11)	0.0353 (11)	0.0358 (11)	0.0078 (9)	0.0073 (9)	0.0131 (9)
N2	0.0418 (13)	0.0407 (12)	0.0411 (12)	0.0107 (10)	0.0118 (10)	0.0145 (10)
N3	0.0470 (14)	0.0434 (13)	0.0374 (12)	0.0028 (11)	0.0026 (10)	0.0064 (10)
O1	0.0579 (13)	0.0618 (13)	0.0494 (12)	0.0312 (11)	0.0195 (10)	0.0201 (10)
O2	0.0402 (10)	0.0429 (10)	0.0418 (10)	−0.0057 (8)	0.0040 (8)	0.0079 (8)
S1	0.0476 (4)	0.0486 (4)	0.0428 (4)	0.0202 (3)	0.0110 (3)	0.0218 (3)
C1	0.0324 (13)	0.0335 (13)	0.0352 (13)	−0.0005 (10)	0.0048 (10)	0.0122 (11)
C2	0.0378 (15)	0.0398 (15)	0.0502 (16)	0.0065 (12)	0.0047 (12)	0.0151 (13)
C3	0.0500 (17)	0.0433 (16)	0.0500 (17)	0.0031 (13)	−0.0066 (14)	0.0203 (13)
C4	0.0621 (19)	0.0510 (17)	0.0363 (15)	−0.0018 (15)	0.0014 (14)	0.0177 (13)
C5	0.0510 (17)	0.0444 (15)	0.0384 (15)	0.0046 (13)	0.0113 (13)	0.0104 (12)
C6	0.0343 (13)	0.0343 (13)	0.0384 (14)	0.0011 (11)	0.0040 (11)	0.0107 (11)
C7	0.0311 (13)	0.0338 (13)	0.0420 (14)	0.0052 (10)	0.0060 (11)	0.0150 (11)
C8	0.0349 (14)	0.0344 (13)	0.0388 (14)	0.0058 (11)	0.0060 (11)	0.0123 (11)
C9	0.0385 (14)	0.0358 (13)	0.0328 (13)	0.0035 (11)	0.0049 (11)	0.0099 (11)
C11	0.0400 (15)	0.0381 (14)	0.0328 (13)	0.0023 (12)	0.0012 (11)	0.0087 (11)
C12	0.0543 (18)	0.0482 (17)	0.0330 (14)	−0.0016 (14)	0.0081 (13)	0.0042 (12)
C13	0.057 (2)	0.072 (2)	0.0460 (17)	0.0006 (16)	0.0133 (15)	0.0091 (16)
C14	0.066 (2)	0.104 (3)	0.065 (2)	0.003 (2)	0.030 (2)	0.009 (2)
C15	0.102 (4)	0.128 (4)	0.070 (3)	0.006 (3)	0.047 (3)	0.027 (3)
C16	0.135 (4)	0.117 (4)	0.048 (2)	0.021 (3)	0.037 (3)	0.033 (2)
C17	0.086 (3)	0.076 (2)	0.0400 (17)	0.0163 (19)	0.0155 (17)	0.0149 (16)
C10	0.033 (5)	0.051 (6)	0.027 (6)	−0.003 (4)	0.002 (4)	0.008 (5)
Cl3	0.076 (3)	0.106 (3)	0.0845 (17)	−0.047 (2)	−0.0034 (18)	0.0290 (17)
C18	0.054 (5)	0.037 (3)	0.033 (4)	−0.008 (3)	0.024 (4)	0.003 (3)
C19	0.071 (5)	0.057 (4)	0.034 (4)	−0.011 (3)	0.012 (4)	0.006 (3)
C20	0.118 (6)	0.042 (4)	0.046 (5)	−0.004 (4)	0.025 (5)	0.012 (4)
C21	0.110 (6)	0.054 (4)	0.050 (5)	0.014 (4)	0.033 (4)	0.022 (4)
C22	0.096 (6)	0.061 (5)	0.050 (5)	0.020 (4)	0.020 (5)	0.025 (4)
C23	0.070 (5)	0.051 (4)	0.044 (4)	0.015 (3)	0.019 (4)	0.023 (3)
C10'	0.044 (8)	0.027 (5)	0.030 (7)	−0.002 (5)	0.002 (5)	0.009 (5)
Cl3'	0.065 (3)	0.095 (3)	0.074 (2)	−0.039 (2)	0.0012 (18)	0.0187 (17)
C18'	0.048 (5)	0.032 (4)	0.033 (4)	0.008 (3)	0.024 (4)	0.011 (3)
C19'	0.062 (5)	0.042 (4)	0.041 (5)	−0.018 (4)	0.009 (4)	0.008 (3)
C20'	0.128 (8)	0.039 (4)	0.051 (6)	−0.015 (5)	0.026 (6)	0.016 (4)
C21'	0.144 (11)	0.036 (5)	0.049 (7)	0.021 (6)	0.032 (9)	0.020 (4)
C22'	0.108 (8)	0.057 (6)	0.046 (6)	0.031 (6)	0.022 (6)	0.023 (5)
C23'	0.059 (7)	0.053 (5)	0.045 (5)	0.014 (4)	0.009 (6)	0.019 (4)
C24	0.0431 (17)	0.0581 (19)	0.0560 (19)	0.0142 (14)	0.0028 (14)	−0.0080 (15)
C25	0.0460 (17)	0.0499 (17)	0.0547 (18)	0.0092 (14)	−0.0028 (14)	0.0024 (14)
O3	0.0429 (11)	0.0537 (12)	0.0443 (11)	0.0068 (9)	−0.0039 (9)	−0.0049 (9)

Geometric parameters (Å, º)

Cl1—C13	1.734 (3)	C16—C17	1.389 (5)
Cl2—C17	1.735 (4)	C16—H16	0.9300
N1—C8	1.373 (3)	C10—C18	1.530 (8)
N1—C7	1.379 (3)	C10—H10	0.9800
N1—C1	1.406 (3)	Cl3—C19	1.724 (8)
N2—C7	1.282 (3)	C18—C19	1.382 (9)
N2—C6	1.417 (3)	C18—C23	1.403 (11)
N3—C11	1.276 (3)	C19—C20	1.413 (12)
N3—O2	1.425 (3)	C20—C21	1.355 (12)
O1—C8	1.196 (3)	C20—H20	0.9300
O2—C9	1.455 (3)	C21—C22	1.368 (11)
S1—C7	1.740 (2)	C21—H21	0.9300
S1—C9	1.832 (3)	C22—C23	1.372 (10)
C1—C2	1.381 (3)	C22—H22	0.9300
C1—C6	1.394 (3)	C23—H23	0.9300
C2—C3	1.384 (4)	C10'—C18'	1.526 (8)
C2—H2	0.9300	C10'—H10'	0.9800
C3—C4	1.383 (4)	Cl3'—C19'	1.732 (6)
C3—H3	0.9300	C18'—C19'	1.3900
C4—C5	1.381 (4)	C18'—C23'	1.3900
C4—H4	0.9300	C19'—C20'	1.3900
C5—C6	1.387 (4)	C20'—C21'	1.3900
C5—H5	0.9300	C20'—H20'	0.9300
C8—C9	1.551 (3)	C21'—C22'	1.3900
C9—C10'	1.537 (11)	C21'—H21'	0.9300
C9—C10	1.547 (9)	C22'—C23'	1.3900
C11—C12	1.483 (4)	C22'—H22'	0.9300
C11—C10'	1.511 (11)	C23'—H23'	0.9300
C11—C10	1.515 (10)	C24—O3	1.427 (3)
C12—C17	1.383 (4)	C24—C25^i	1.499 (4)
C12—C13	1.398 (4)	C24—H24A	0.9700
C13—C14	1.374 (4)	C24—H24B	0.9700
C14—C15	1.365 (6)	C25—O3	1.424 (3)
C14—H14	0.9300	C25—C24^i	1.499 (4)
C15—C16	1.372 (6)	C25—H25A	0.9700
C15—H15	0.9300	C25—H25B	0.9700
C8—N1—C7	117.87 (19)	C12—C17—Cl2	120.2 (3)
C8—N1—C1	135.7 (2)	C16—C17—Cl2	118.6 (3)
C7—N1—C1	106.12 (19)	C11—C10—C18	113.5 (9)
C7—N2—C6	103.5 (2)	C11—C10—C9	99.1 (6)
C11—N3—O2	108.8 (2)	C18—C10—C9	113.1 (8)
N3—O2—C9	109.15 (18)	C11—C10—H10	110.2
C7—S1—C9	91.46 (11)	C18—C10—H10	110.2
C2—C1—C6	123.0 (2)	C9—C10—H10	110.2
C2—C1—N1	133.1 (2)	C19—C18—C23	117.3 (7)
C6—C1—N1	103.9 (2)	C19—C18—C10	121.5 (8)
C1—C2—C3	115.9 (3)	C23—C18—C10	120.4 (8)
C1—C2—H2	122.1	C18—C19—C20	120.2 (8)
C3—C2—H2	122.1	C18—C19—Cl3	121.6 (7)
C4—C3—C2	122.0 (3)	C20—C19—Cl3	118.2 (6)
C4—C3—H3	119.0	C21—C20—C19	119.6 (9)
C2—C3—H3	119.0	C21—C20—H20	120.2
C5—C4—C3	121.7 (3)	C19—C20—H20	120.2
C5—C4—H4	119.1	C20—C21—C22	121.4 (9)
C3—C4—H4	119.1	C20—C21—H21	119.3
C4—C5—C6	117.3 (3)	C22—C21—H21	119.3
C4—C5—H5	121.3	C21—C22—C23	119.1 (9)
C6—C5—H5	121.3	C21—C22—H22	120.4
C5—C6—C1	120.1 (2)	C23—C22—H22	120.4
C5—C6—N2	128.6 (2)	C22—C23—C18	121.9 (9)
C1—C6—N2	111.4 (2)	C22—C23—H23	119.1
N2—C7—N1	115.1 (2)	C18—C23—H23	119.1
N2—C7—S1	131.81 (19)	C11—C10'—C18'	105.9 (9)
N1—C7—S1	113.03 (18)	C11—C10'—C9	99.7 (7)
O1—C8—N1	125.6 (2)	C18'—C10'—C9	118.6 (10)
O1—C8—C9	124.6 (2)	C11—C10'—H10'	110.6
N1—C8—C9	109.8 (2)	C18'—C10'—H10'	110.6
O2—C9—C10'	105.4 (5)	C9—C10'—H10'	110.6
O2—C9—C10	103.9 (5)	C19'—C18'—C23'	120.0
C10'—C9—C10	6.1 (10)	C19'—C18'—C10'	120.4 (7)
O2—C9—C8	105.52 (19)	C23'—C18'—C10'	119.0 (7)
C10'—C9—C8	109.5 (6)	C18'—C19'—C20'	120.0
C10—C9—C8	115.5 (6)	C18'—C19'—Cl3'	121.4 (4)
O2—C9—S1	109.64 (16)	C20'—C19'—Cl3'	118.5 (4)
C10'—C9—S1	118.7 (4)	C21'—C20'—C19'	120.0
C10—C9—S1	114.4 (4)	C21'—C20'—H20'	120.0
C8—C9—S1	107.35 (16)	C19'—C20'—H20'	120.0
N3—C11—C12	122.3 (2)	C20'—C21'—C22'	120.0
N3—C11—C10'	115.2 (5)	C20'—C21'—H21'	120.0
C12—C11—C10'	122.5 (5)	C22'—C21'—H21'	120.0
N3—C11—C10	114.3 (5)	C23'—C22'—C21'	120.0
C12—C11—C10	123.1 (4)	C23'—C22'—H22'	120.0
C10'—C11—C10	6.3 (10)	C21'—C22'—H22'	120.0
C17—C12—C13	116.4 (3)	C22'—C23'—C18'	120.0
C17—C12—C11	123.4 (3)	C22'—C23'—H23'	120.0
C13—C12—C11	120.1 (2)	C18'—C23'—H23'	120.0
C14—C13—C12	123.1 (3)	O3—C24—C25^i	110.8 (2)
C14—C13—Cl1	118.2 (3)	O3—C24—H24A	109.5
C12—C13—Cl1	118.7 (2)	C25^i—C24—H24A	109.5
C15—C14—C13	118.2 (4)	O3—C24—H24B	109.5
C15—C14—H14	120.9	C25^i—C24—H24B	109.5
C13—C14—H14	120.9	H24A—C24—H24B	108.1
C14—C15—C16	121.3 (4)	O3—C25—C24^i	110.2 (2)
C14—C15—H15	119.4	O3—C25—H25A	109.6
C16—C15—H15	119.4	C24^i—C25—H25A	109.6
C15—C16—C17	119.6 (4)	O3—C25—H25B	109.6
C15—C16—H16	120.2	C24^i—C25—H25B	109.6
C17—C16—H16	120.2	H25A—C25—H25B	108.1
C12—C17—C16	121.2 (4)	C25—O3—C24	109.2 (2)
C11—N3—O2—C9	9.5 (3)	C13—C12—C17—Cl2	−177.1 (3)
C8—N1—C1—C2	6.6 (5)	C11—C12—C17—Cl2	5.2 (5)
C7—N1—C1—C2	−179.8 (3)	C15—C16—C17—C12	−2.0 (7)
C8—N1—C1—C6	−173.8 (3)	C15—C16—C17—Cl2	177.8 (4)
C7—N1—C1—C6	−0.1 (3)	N3—C11—C10—C18	103.2 (7)
C6—C1—C2—C3	0.2 (4)	C12—C11—C10—C18	−70.9 (10)
N1—C1—C2—C3	179.7 (3)	C10'—C11—C10—C18	−157 (8)
C1—C2—C3—C4	−1.0 (4)	N3—C11—C10—C9	−17.0 (9)
C2—C3—C4—C5	0.7 (5)	C12—C11—C10—C9	169.0 (4)
C3—C4—C5—C6	0.3 (4)	C10'—C11—C10—C9	83 (7)
C4—C5—C6—C1	−1.1 (4)	O2—C9—C10—C11	20.5 (8)
C4—C5—C6—N2	−179.9 (3)	C10'—C9—C10—C11	−84 (7)
C2—C1—C6—C5	0.9 (4)	C8—C9—C10—C11	−94.5 (7)
N1—C1—C6—C5	−178.8 (2)	S1—C9—C10—C11	140.0 (5)
C2—C1—C6—N2	179.9 (2)	O2—C9—C10—C18	−99.9 (8)
N1—C1—C6—N2	0.2 (3)	C10'—C9—C10—C18	155 (8)
C7—N2—C6—C5	178.7 (3)	C8—C9—C10—C18	145.0 (7)
C7—N2—C6—C1	−0.2 (3)	S1—C9—C10—C18	19.6 (10)
C6—N2—C7—N1	0.1 (3)	C11—C10—C18—C19	106.8 (11)
C6—N2—C7—S1	177.8 (2)	C9—C10—C18—C19	−141.3 (9)
C8—N1—C7—N2	175.0 (2)	C11—C10—C18—C23	−63.0 (11)
C1—N1—C7—N2	0.0 (3)	C9—C10—C18—C23	48.9 (12)
C8—N1—C7—S1	−3.1 (3)	C23—C18—C19—C20	−8.5 (11)
C1—N1—C7—S1	−178.11 (17)	C10—C18—C19—C20	−178.5 (13)
C9—S1—C7—N2	−179.2 (3)	C23—C18—C19—Cl3	172.5 (8)
C9—S1—C7—N1	−1.5 (2)	C10—C18—C19—Cl3	2.4 (13)
C7—N1—C8—O1	−175.5 (3)	C18—C19—C20—C21	5.3 (17)
C1—N1—C8—O1	−2.4 (5)	Cl3—C19—C20—C21	−175.7 (10)
C7—N1—C8—C9	7.0 (3)	C19—C20—C21—C22	1 (2)
C1—N1—C8—C9	−180.0 (3)	C20—C21—C22—C23	−2.9 (18)
N3—O2—C9—C10'	−13.4 (6)	C21—C22—C23—C18	−0.7 (12)
N3—O2—C9—C10	−19.6 (5)	C19—C18—C23—C22	6.3 (10)
N3—O2—C9—C8	102.4 (2)	C10—C18—C23—C22	176.4 (12)
N3—O2—C9—S1	−142.26 (16)	N3—C11—C10'—C18'	116.8 (7)
O1—C8—C9—O2	−68.1 (3)	C12—C11—C10'—C18'	−64.2 (11)
N1—C8—C9—O2	109.5 (2)	C10—C11—C10'—C18'	33 (7)
O1—C8—C9—C10'	44.9 (5)	N3—C11—C10'—C9	−6.9 (10)
N1—C8—C9—C10'	−137.5 (5)	C12—C11—C10'—C9	172.2 (4)
O1—C8—C9—C10	46.0 (5)	C10—C11—C10'—C9	−90 (8)
N1—C8—C9—C10	−136.4 (4)	O2—C9—C10'—C11	11.6 (9)
O1—C8—C9—S1	175.0 (2)	C10—C9—C10'—C11	88 (7)
N1—C8—C9—S1	−7.4 (2)	C8—C9—C10'—C11	−101.4 (7)
C7—S1—C9—O2	−109.22 (16)	S1—C9—C10'—C11	134.9 (5)
C7—S1—C9—C10'	129.7 (7)	O2—C9—C10'—C18'	−102.5 (10)
C7—S1—C9—C10	134.6 (6)	C10—C9—C10'—C18'	−26 (6)
C7—S1—C9—C8	4.93 (18)	C8—C9—C10'—C18'	144.4 (9)
O2—N3—C11—C12	179.8 (2)	S1—C9—C10'—C18'	20.7 (13)
O2—N3—C11—C10'	−1.1 (7)	C11—C10'—C18'—C19'	116.6 (10)
O2—N3—C11—C10	5.7 (6)	C9—C10'—C18'—C19'	−132.7 (10)
N3—C11—C12—C17	−74.5 (4)	C11—C10'—C18'—C23'	−72.3 (11)
C10'—C11—C12—C17	106.5 (7)	C9—C10'—C18'—C23'	38.4 (13)
C10—C11—C12—C17	99.1 (7)	C23'—C18'—C19'—C20'	0.0
N3—C11—C12—C13	107.9 (3)	C10'—C18'—C19'—C20'	171.0 (12)
C10'—C11—C12—C13	−71.1 (7)	C23'—C18'—C19'—Cl3'	175.4 (9)
C10—C11—C12—C13	−78.5 (7)	C10'—C18'—C19'—Cl3'	−13.5 (10)
C17—C12—C13—C14	−1.2 (5)	C18'—C19'—C20'—C21'	0.0
C11—C12—C13—C14	176.6 (3)	Cl3'—C19'—C20'—C21'	−175.6 (8)
C17—C12—C13—Cl1	176.9 (3)	C19'—C20'—C21'—C22'	0.0
C11—C12—C13—Cl1	−5.3 (4)	C20'—C21'—C22'—C23'	0.0
C12—C13—C14—C15	−1.0 (6)	C21'—C22'—C23'—C18'	0.0
Cl1—C13—C14—C15	−179.0 (3)	C19'—C18'—C23'—C22'	0.0
C13—C14—C15—C16	1.7 (7)	C10'—C18'—C23'—C22'	−171.2 (12)
C14—C15—C16—C17	−0.3 (8)	C24^i—C25—O3—C24	58.1 (3)
C13—C12—C17—C16	2.7 (5)	C25^i—C24—O3—C25	−58.5 (4)
C11—C12—C17—C16	−175.0 (3)

Symmetry code: (i) −x+1, −y+1, −z.