1′-Methyl-4′-(2,4-di­chloro­phenyl)-1H-indole-3-spiro-2′-pyrrolidine-3′-spiro-5′′-(thia­zolo­[3,2-b][1,2,4]­triazole)-2,6′′(3H,5′′H)-dione

The title compound, C₂₁H₁₅Cl₂N₅O₂S, was synthesized by the intermolecular [3 + 2]-cyclo­addition of the azomethine yl­ide derived from isatin and sarcosine by a de­carboxyl­ative route and 5-(2,4-di­chloro­benzyl­idene)­thia­zolo­[3,2-b][1,2,4]­triazol-6-one. In the mol­ecule, the two spiro junctions link a planar 2-ox­indole ring, a pyrrolidine ring in an envelope conformation and a thia­zolo­[3,2-b][1,2,4]­triazol-6-one ring. The 2,4-di­chloro­phenyl group is disordered. Molecules are connected into chains by intermolecular N—H...N hydrogen bonds and weak C—H...O interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.047
• wR factor = 0.119
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT432_ALERT_2_B Short Inter X...Y Contact  C19'   ..  C19'     =       3.08 Ang.

Alert level C
PLAT165_ALERT_3_C Nr. of Status R Flagged Non-Hydrogen Atoms .....         12
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C18
PLAT301_ALERT_3_C Main Residue  Disorder .........................      23.00 Perc.
PLAT410_ALERT_2_C Short Intra H...H Contact  H14B   ..  H20'     =       1.92 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  S1       =       3.51 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  C19    ..  C19      =       3.19 Ang.

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

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

---

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.

1'-Methyl-4'-(2,4-dichlorophenyl)-1H-indole-3-spiro-2'-pyrrolidine-3'-spiro- 5''-(thiazolo[3,2-b][1,2,4]triazole)-2,6''(3H,5''H)-dione

Crystal data

C21H15Cl2N5O2S	F(000) = 968
Mr = 472.34	Dx = 1.485 Mg m^−3
Monoclinic, P21/c	Melting point = 495–496 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 20.130 (6) Å	Cell parameters from 886 reflections
b = 6.357 (2) Å	θ = 3.2–26.0°
c = 17.394 (5) Å	µ = 0.44 mm^−1
β = 108.369 (5)°	T = 293 K
V = 2112.6 (11) Å^3	Block, colorless
Z = 4	0.24 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer	4299 independent reflections
Radiation source: fine-focus sealed tube	2878 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
φ and ω scans	θmax = 26.4°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −25→13
Tmin = 0.825, Tmax = 0.960	k = −7→7
11420 measured reflections	l = −21→21

Refinement

Refinement on F^2	336 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.047	w = 1/[σ^2(Fo^2) + (0.084P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.119	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.26 e Å^−3
4299 reflections	Δρmin = −0.24 e Å^−3
330 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)
S1	0.23947 (4)	0.90593 (9)	0.43845 (4)	0.0445 (2)
N1	0.12918 (11)	0.6723 (3)	0.38539 (12)	0.0434 (5)
N2	0.06533 (13)	0.6393 (4)	0.32744 (14)	0.0604 (7)
N3	0.11655 (15)	0.9474 (4)	0.30607 (14)	0.0607 (7)
N4	0.25902 (10)	0.5539 (3)	0.63284 (11)	0.0330 (4)
N5	0.21438 (11)	1.0824 (3)	0.62151 (12)	0.0394 (5)
H5	0.2231	1.2112	0.6364	0.047*
C1	0.23347 (12)	0.6694 (3)	0.49798 (14)	0.0323 (5)
C2	0.16842 (13)	0.5466 (4)	0.44840 (14)	0.0374 (6)
C3	0.06130 (19)	0.8070 (6)	0.28353 (19)	0.0679 (9)
H3	0.0225	0.8319	0.2384	0.081*
C4	0.15774 (14)	0.8550 (4)	0.37074 (15)	0.0444 (6)
C5	0.22482 (12)	0.7318 (3)	0.58196 (13)	0.0312 (5)
C6	0.26197 (13)	0.9492 (3)	0.60941 (15)	0.0375 (6)
C7	0.14864 (13)	0.9865 (3)	0.60700 (14)	0.0360 (5)
C8	0.08830 (15)	1.0707 (4)	0.61679 (17)	0.0503 (7)
H8	0.0869	1.2089	0.6337	0.060*
C9	0.03044 (15)	0.9419 (5)	0.60047 (17)	0.0555 (7)
H9	−0.0113	0.9962	0.6044	0.067*
C10	0.03293 (14)	0.7356 (4)	0.57859 (16)	0.0499 (7)
H10	−0.0067	0.6515	0.5690	0.060*
C11	0.09377 (13)	0.6513 (4)	0.57072 (14)	0.0407 (6)
H11	0.0956	0.5107	0.5568	0.049*
C12	0.15160 (12)	0.7784 (3)	0.58369 (13)	0.0310 (5)
C14	0.32372 (12)	0.5151 (4)	0.61328 (15)	0.0405 (6)
H14A	0.3435	0.3790	0.6333	0.049*
H14B	0.3583	0.6234	0.6361	0.049*
O1	0.15312 (10)	0.3721 (3)	0.46249 (11)	0.0493 (5)
O2	0.32307 (9)	0.9875 (3)	0.61800 (13)	0.0566 (5)
Cl1	0.2553 (3)	0.3761 (7)	0.3403 (3)	0.0634 (9)	0.542 (10)
Cl2	0.4976 (3)	0.6964 (15)	0.3305 (4)	0.140 (2)	0.542 (10)
C13	0.29955 (13)	0.5216 (4)	0.52101 (15)	0.0400 (6)	0.542 (10)
H13	0.2805	0.3809	0.5045	0.048*	0.542 (10)
C15	0.3480 (3)	0.5637 (10)	0.4698 (4)	0.0401 (18)	0.542 (10)
C16	0.3331 (3)	0.4959 (9)	0.3902 (3)	0.0512 (19)	0.542 (10)
C17	0.3802 (4)	0.5349 (10)	0.3481 (3)	0.062 (2)	0.542 (10)
H17	0.3702	0.4896	0.2948	0.075*	0.542 (10)
C18	0.4422 (3)	0.6416 (12)	0.3857 (4)	0.063 (2)	0.542 (10)
C19	0.4571 (2)	0.7093 (11)	0.4653 (4)	0.072 (2)	0.542 (10)
H19	0.4986	0.7807	0.4905	0.087*	0.542 (10)
C20	0.4100 (3)	0.6704 (11)	0.5074 (4)	0.0582 (19)	0.542 (10)
H20	0.4200	0.7157	0.5607	0.070*	0.542 (10)
Cl1'	0.2834 (4)	0.4032 (10)	0.3523 (4)	0.0802 (14)	0.458 (10)
Cl2'	0.5225 (3)	0.8059 (8)	0.3775 (6)	0.119 (2)	0.458 (10)
C13'	0.29955 (13)	0.5216 (4)	0.52101 (15)	0.0400 (6)	0.458 (10)
H13'	0.2849	0.3801	0.5002	0.048*	0.458 (10)
C15'	0.3623 (3)	0.5917 (12)	0.4919 (5)	0.042 (2)	0.458 (10)
C16'	0.3559 (3)	0.5355 (11)	0.4126 (4)	0.048 (2)	0.458 (10)
C17'	0.4057 (4)	0.6016 (11)	0.3778 (5)	0.057 (2)	0.458 (10)
H17'	0.4014	0.5640	0.3247	0.069*	0.458 (10)
C18'	0.4619 (3)	0.7239 (11)	0.4222 (5)	0.070 (3)	0.458 (10)
C19'	0.4684 (3)	0.7801 (10)	0.5014 (5)	0.078 (3)	0.458 (10)
H19'	0.5060	0.8619	0.5311	0.093*	0.458 (10)
C20'	0.4186 (4)	0.7140 (12)	0.5363 (4)	0.067 (2)	0.458 (10)
H20'	0.4229	0.7516	0.5893	0.081*	0.458 (10)
C21	0.27025 (16)	0.5846 (4)	0.71935 (15)	0.0519 (7)
H21A	0.2992	0.7060	0.7379	0.078*
H21B	0.2929	0.4628	0.7487	0.078*
H21C	0.2260	0.6051	0.7282	0.078*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0536 (4)	0.0335 (3)	0.0525 (4)	0.0032 (3)	0.0254 (3)	0.0128 (3)
N1	0.0468 (13)	0.0463 (12)	0.0343 (12)	0.0026 (10)	0.0088 (10)	−0.0015 (10)
N2	0.0570 (16)	0.0757 (17)	0.0387 (14)	0.0088 (13)	0.0011 (12)	−0.0091 (13)
N3	0.0782 (18)	0.0654 (16)	0.0410 (14)	0.0299 (14)	0.0221 (13)	0.0137 (12)
N4	0.0371 (11)	0.0280 (9)	0.0330 (11)	−0.0004 (8)	0.0099 (9)	0.0014 (8)
N5	0.0523 (13)	0.0218 (9)	0.0458 (12)	−0.0038 (9)	0.0178 (10)	−0.0063 (8)
C1	0.0366 (13)	0.0260 (10)	0.0375 (13)	0.0016 (9)	0.0164 (11)	0.0051 (10)
C2	0.0470 (15)	0.0356 (13)	0.0331 (13)	−0.0015 (11)	0.0177 (11)	−0.0048 (10)
C3	0.070 (2)	0.088 (2)	0.0388 (17)	0.0277 (19)	0.0065 (15)	−0.0047 (17)
C4	0.0567 (17)	0.0456 (14)	0.0366 (15)	0.0149 (13)	0.0229 (13)	0.0035 (11)
C5	0.0348 (13)	0.0239 (10)	0.0345 (13)	−0.0044 (9)	0.0103 (10)	−0.0011 (9)
C6	0.0429 (15)	0.0265 (11)	0.0410 (15)	−0.0054 (11)	0.0102 (11)	0.0008 (10)
C7	0.0460 (14)	0.0299 (11)	0.0355 (14)	0.0009 (11)	0.0175 (11)	0.0042 (10)
C8	0.0656 (19)	0.0383 (13)	0.0573 (18)	0.0127 (13)	0.0338 (15)	0.0049 (12)
C9	0.0485 (17)	0.0675 (19)	0.0609 (19)	0.0130 (15)	0.0322 (15)	0.0114 (15)
C10	0.0391 (15)	0.0637 (17)	0.0519 (17)	−0.0068 (13)	0.0213 (13)	0.0036 (14)
C11	0.0422 (15)	0.0425 (13)	0.0390 (15)	−0.0060 (11)	0.0148 (12)	−0.0007 (11)
C12	0.0349 (13)	0.0299 (11)	0.0291 (12)	0.0006 (10)	0.0113 (10)	0.0018 (9)
C14	0.0342 (14)	0.0300 (12)	0.0553 (17)	0.0002 (10)	0.0110 (12)	0.0045 (11)
O1	0.0632 (12)	0.0366 (9)	0.0472 (11)	−0.0113 (8)	0.0162 (9)	−0.0072 (8)
O2	0.0396 (11)	0.0342 (9)	0.0937 (16)	−0.0103 (8)	0.0176 (10)	−0.0037 (9)
Cl1	0.092 (3)	0.0590 (14)	0.0448 (13)	0.0114 (15)	0.0300 (17)	−0.0024 (9)
Cl2	0.093 (2)	0.217 (5)	0.147 (3)	0.050 (3)	0.089 (2)	0.087 (3)
C13	0.0441 (14)	0.0297 (11)	0.0512 (16)	0.0035 (10)	0.0220 (12)	0.0042 (11)
C15	0.029 (3)	0.036 (3)	0.054 (4)	0.010 (2)	0.012 (3)	0.010 (3)
C16	0.050 (4)	0.055 (4)	0.049 (4)	0.021 (3)	0.016 (4)	0.013 (3)
C17	0.064 (4)	0.076 (4)	0.057 (4)	0.037 (4)	0.033 (4)	0.023 (3)
C18	0.045 (4)	0.076 (5)	0.079 (5)	0.015 (4)	0.035 (4)	0.029 (4)
C19	0.053 (4)	0.075 (5)	0.096 (6)	0.010 (3)	0.034 (4)	0.016 (4)
C20	0.040 (4)	0.065 (4)	0.078 (4)	−0.002 (3)	0.030 (3)	0.010 (3)
Cl1'	0.107 (4)	0.084 (2)	0.062 (2)	−0.007 (2)	0.045 (3)	−0.0083 (16)
Cl2'	0.101 (3)	0.120 (3)	0.179 (5)	0.024 (2)	0.106 (3)	0.064 (3)
C13'	0.0441 (14)	0.0297 (11)	0.0512 (16)	0.0035 (10)	0.0220 (12)	0.0042 (11)
C15'	0.048 (5)	0.041 (4)	0.042 (4)	0.009 (3)	0.021 (4)	0.012 (3)
C16'	0.048 (4)	0.057 (4)	0.047 (5)	0.016 (3)	0.026 (4)	0.008 (4)
C17'	0.050 (5)	0.068 (5)	0.061 (5)	0.008 (4)	0.028 (4)	0.020 (4)
C18'	0.064 (5)	0.070 (5)	0.089 (6)	0.015 (4)	0.045 (5)	0.016 (5)
C19'	0.064 (5)	0.068 (5)	0.106 (6)	−0.007 (4)	0.035 (4)	0.015 (5)
C20'	0.055 (5)	0.062 (5)	0.089 (6)	−0.006 (4)	0.030 (4)	0.018 (4)
C21	0.0676 (19)	0.0469 (15)	0.0363 (15)	0.0004 (13)	0.0094 (13)	0.0016 (12)

Geometric parameters (Å, º)

S1—C4	1.726 (3)	C11—H11	0.9300
S1—C1	1.851 (2)	C14—C13	1.524 (3)
N1—C4	1.356 (3)	C14—H14A	0.9700
N1—N2	1.377 (3)	C14—H14B	0.9700
N1—C2	1.385 (3)	Cl1—C16	1.710 (4)
N2—C3	1.300 (4)	Cl2—C18	1.720 (4)
N3—C4	1.308 (3)	C13—C15	1.537 (4)
N3—C3	1.383 (4)	C13—H13	0.9800
N4—C21	1.463 (3)	C15—C16	1.3900
N4—C14	1.467 (3)	C15—C20	1.3900
N4—C5	1.467 (3)	C16—C17	1.3900
N5—C6	1.344 (3)	C17—C18	1.3900
N5—C7	1.406 (3)	C17—H17	0.9300
N5—H5	0.8600	C18—C19	1.3900
C1—C2	1.535 (3)	C19—C20	1.3900
C1—C13	1.574 (3)	C19—H19	0.9300
C1—C5	1.575 (3)	C20—H20	0.9300
C2—O1	1.197 (3)	Cl1'—C16'	1.724 (5)
C3—H3	0.9300	Cl2'—C18'	1.720 (5)
C5—C12	1.513 (3)	C15'—C16'	1.3900
C5—C6	1.572 (3)	C15'—C20'	1.3900
C6—O2	1.216 (3)	C16'—C17'	1.3900
C7—C8	1.386 (3)	C17'—C18'	1.3900
C7—C12	1.391 (3)	C17'—H17'	0.9300
C8—C9	1.378 (4)	C18'—C19'	1.3900
C8—H8	0.9300	C19'—C20'	1.3900
C9—C10	1.371 (4)	C19'—H19'	0.9300
C9—H9	0.9300	C20'—H20'	0.9300
C10—C11	1.383 (3)	C21—H21A	0.9600
C10—H10	0.9300	C21—H21B	0.9600
C11—C12	1.376 (3)	C21—H21C	0.9600
C4—S1—C1	90.76 (11)	C7—C12—C5	108.88 (19)
C4—N1—N2	110.3 (2)	N4—C14—C13	103.16 (19)
C4—N1—C2	118.3 (2)	N4—C14—H14A	111.1
N2—N1—C2	131.3 (2)	C13—C14—H14A	111.1
C3—N2—N1	100.1 (3)	N4—C14—H14B	111.1
C4—N3—C3	100.9 (2)	C13—C14—H14B	111.1
C21—N4—C14	113.6 (2)	H14A—C14—H14B	109.1
C21—N4—C5	114.13 (18)	C14—C13—C15	124.4 (3)
C14—N4—C5	105.77 (16)	C14—C13—C1	104.36 (18)
C6—N5—C7	112.09 (19)	C15—C13—C1	112.9 (3)
C6—N5—H5	124.0	C14—C13—H13	104.4
C7—N5—H5	124.0	C15—C13—H13	104.4
C2—C1—C13	110.00 (17)	C1—C13—H13	104.4
C2—C1—C5	108.97 (17)	C16—C15—C20	120.0
C13—C1—C5	104.23 (18)	C16—C15—C13	123.1 (3)
C2—C1—S1	107.07 (16)	C20—C15—C13	116.9 (3)
C13—C1—S1	115.36 (15)	C15—C16—C17	120.0
C5—C1—S1	111.10 (14)	C15—C16—Cl1	121.3 (3)
O1—C2—N1	125.3 (2)	C17—C16—Cl1	118.7 (3)
O1—C2—C1	125.8 (2)	C18—C17—C16	120.0
N1—C2—C1	108.89 (19)	C18—C17—H17	120.0
N2—C3—N3	117.9 (3)	C16—C17—H17	120.0
N2—C3—H3	121.1	C17—C18—C19	120.0
N3—C3—H3	121.1	C17—C18—Cl2	118.7 (3)
N3—C4—N1	110.8 (3)	C19—C18—Cl2	121.2 (3)
N3—C4—S1	135.4 (2)	C20—C19—C18	120.0
N1—C4—S1	113.70 (19)	C20—C19—H19	120.0
N4—C5—C12	114.44 (17)	C18—C19—H19	120.0
N4—C5—C6	114.00 (18)	C19—C20—C15	120.0
C12—C5—C6	101.24 (17)	C19—C20—H20	120.0
N4—C5—C1	101.38 (16)	C15—C20—H20	120.0
C12—C5—C1	117.44 (18)	C16'—C15'—C20'	120.0
C6—C5—C1	108.78 (17)	C15'—C16'—C17'	120.0
O2—C6—N5	126.7 (2)	C15'—C16'—Cl1'	121.7 (3)
O2—C6—C5	125.4 (2)	C17'—C16'—Cl1'	118.1 (3)
N5—C6—C5	107.9 (2)	C16'—C17'—C18'	120.0
C8—C7—C12	121.5 (2)	C16'—C17'—H17'	120.0
C8—C7—N5	128.5 (2)	C18'—C17'—H17'	120.0
C12—C7—N5	109.90 (19)	C17'—C18'—C19'	120.0
C9—C8—C7	117.5 (2)	C17'—C18'—Cl2'	119.2 (3)
C9—C8—H8	121.2	C19'—C18'—Cl2'	120.8 (3)
C7—C8—H8	121.2	C20'—C19'—C18'	120.0
C10—C9—C8	121.5 (2)	C20'—C19'—H19'	120.0
C10—C9—H9	119.2	C18'—C19'—H19'	120.0
C8—C9—H9	119.2	C19'—C20'—C15'	120.0
C9—C10—C11	120.6 (2)	C19'—C20'—H20'	120.0
C9—C10—H10	119.7	C15'—C20'—H20'	120.0
C11—C10—H10	119.7	N4—C21—H21A	109.5
C12—C11—C10	119.1 (2)	N4—C21—H21B	109.5
C12—C11—H11	120.4	H21A—C21—H21B	109.5
C10—C11—H11	120.4	N4—C21—H21C	109.5
C11—C12—C7	119.6 (2)	H21A—C21—H21C	109.5
C11—C12—C5	131.4 (2)	H21B—C21—H21C	109.5
C4—N1—N2—C3	−0.4 (3)	C7—C8—C9—C10	2.7 (4)
C2—N1—N2—C3	−174.8 (2)	C8—C9—C10—C11	−1.3 (4)
C4—S1—C1—C2	9.13 (15)	C9—C10—C11—C12	−1.2 (4)
C4—S1—C1—C13	131.92 (18)	C10—C11—C12—C7	2.1 (3)
C4—S1—C1—C5	−109.75 (16)	C10—C11—C12—C5	178.1 (2)
C4—N1—C2—O1	−171.4 (2)	C8—C7—C12—C11	−0.7 (4)
N2—N1—C2—O1	2.6 (4)	N5—C7—C12—C11	176.5 (2)
C4—N1—C2—C1	9.9 (3)	C8—C7—C12—C5	−177.5 (2)
N2—N1—C2—C1	−176.1 (2)	N5—C7—C12—C5	−0.4 (3)
C13—C1—C2—O1	43.3 (3)	N4—C5—C12—C11	−52.6 (3)
C5—C1—C2—O1	−70.4 (3)	C6—C5—C12—C11	−175.6 (2)
S1—C1—C2—O1	169.4 (2)	C1—C5—C12—C11	66.1 (3)
C13—C1—C2—N1	−138.00 (19)	N4—C5—C12—C7	123.8 (2)
C5—C1—C2—N1	108.3 (2)	C6—C5—C12—C7	0.7 (2)
S1—C1—C2—N1	−11.9 (2)	C1—C5—C12—C7	−117.5 (2)
N1—N2—C3—N3	0.7 (3)	C21—N4—C14—C13	−171.89 (18)
C4—N3—C3—N2	−0.6 (3)	C5—N4—C14—C13	−46.0 (2)
C3—N3—C4—N1	0.3 (3)	N4—C14—C13—C15	158.6 (3)
C3—N3—C4—S1	177.7 (2)	N4—C14—C13—C1	27.2 (2)
N2—N1—C4—N3	0.1 (3)	C2—C1—C13—C14	−117.87 (19)
C2—N1—C4—N3	175.3 (2)	C5—C1—C13—C14	−1.2 (2)
N2—N1—C4—S1	−177.94 (16)	S1—C1—C13—C14	120.91 (17)
C2—N1—C4—S1	−2.7 (3)	C2—C1—C13—C15	104.3 (3)
C1—S1—C4—N3	178.3 (3)	C5—C1—C13—C15	−139.0 (3)
C1—S1—C4—N1	−4.30 (18)	S1—C1—C13—C15	−16.9 (4)
C21—N4—C5—C12	−62.8 (3)	C14—C13—C15—C16	155.6 (3)
C14—N4—C5—C12	171.60 (18)	C1—C13—C15—C16	−76.5 (4)
C21—N4—C5—C6	53.1 (3)	C14—C13—C15—C20	−22.8 (4)
C14—N4—C5—C6	−72.5 (2)	C1—C13—C15—C20	105.1 (3)
C21—N4—C5—C1	169.80 (19)	C20—C15—C16—C17	0.0
C14—N4—C5—C1	44.2 (2)	C13—C15—C16—C17	−178.3 (5)
C2—C1—C5—N4	92.31 (19)	C20—C15—C16—Cl1	−176.6 (4)
C13—C1—C5—N4	−25.1 (2)	C13—C15—C16—Cl1	5.0 (4)
S1—C1—C5—N4	−149.96 (14)	C15—C16—C17—C18	0.0
C2—C1—C5—C12	−33.1 (2)	Cl1—C16—C17—C18	176.7 (4)
C13—C1—C5—C12	−150.54 (18)	C16—C17—C18—C19	0.0
S1—C1—C5—C12	84.6 (2)	C16—C17—C18—Cl2	−177.4 (4)
C2—C1—C5—C6	−147.25 (18)	C17—C18—C19—C20	0.0
C13—C1—C5—C6	95.3 (2)	Cl2—C18—C19—C20	177.3 (4)
S1—C1—C5—C6	−29.5 (2)	C18—C19—C20—C15	0.0
C7—N5—C6—O2	−179.3 (2)	C16—C15—C20—C19	0.0
C7—N5—C6—C5	0.6 (3)	C13—C15—C20—C19	178.5 (5)
N4—C5—C6—O2	55.7 (3)	C20'—C15'—C16'—C17'	0.0
C12—C5—C6—O2	179.1 (2)	C20'—C15'—C16'—Cl1'	−174.4 (4)
C1—C5—C6—O2	−56.6 (3)	C15'—C16'—C17'—C18'	0.0
N4—C5—C6—N5	−124.2 (2)	Cl1'—C16'—C17'—C18'	174.6 (4)
C12—C5—C6—N5	−0.8 (2)	C16'—C17'—C18'—C19'	0.0
C1—C5—C6—N5	123.5 (2)	C16'—C17'—C18'—Cl2'	−179.4 (4)
C6—N5—C7—C8	176.7 (2)	C17'—C18'—C19'—C20'	0.0
C6—N5—C7—C12	−0.2 (3)	Cl2'—C18'—C19'—C20'	179.4 (4)
C12—C7—C8—C9	−1.7 (4)	C18'—C19'—C20'—C15'	0.0
N5—C7—C8—C9	−178.2 (2)	C16'—C15'—C20'—C19'	0.0