7-(Piperidin-1-yl)-2-propyl-4-oxa-5-thia-1,6,7a-triaza­indene 5,5-dioxide, a derivative of a new ring system

The title compound, C₁₂H₁₈N₄O₃S, is the first example of a fused dicyclic hexa­hydro-4-oxa-5-thia-1,6,7a-triazaindene ring system. The structure comprises two mol­ecules in the asymmetric unit, which differ in terms of the orientation of their pendant n-propyl groups.

Key indicators

• Single-crystal X-ray study
• T = 123 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.042
• wR factor = 0.102
• Data-to-parameter ratio = 18.4

checkCIF/PLATON results

No syntax errors found





Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.61 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.52 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   2 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
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

7-(Piperidin-1-yl)-2-propyl-4-oxa-5-thia-1,6,7a-triazaindene 5,5-dioxide

Crystal data

C12H18N4O3S	Z = 4
Mr = 298.36	F(000) = 632
Triclinic, P1	Dx = 1.448 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6834 (1) Å	Cell parameters from 18009 reflections
b = 11.9792 (2) Å	θ = 1.6–28.3°
c = 13.5579 (2) Å	µ = 0.25 mm^−1
α = 82.820 (1)°	T = 123 K
β = 69.571 (1)°	Prismatic, colourless
γ = 68.184 (1)°	0.25 × 0.20 × 0.18 mm
V = 1368.22 (4) Å^3

Data collection

Nonius KappaCCD area-detector diffractometer	4307 reflections with I > 2σ(I)
Radiation source: Enraf–Nonius FR590	Rint = 0.045
Horizonally mounted graphite crystal monochromator	θmax = 28.3°, θmin = 2.4°
Detector resolution: 9 pixels mm^-1	h = −12→12
CCD rotation images, thick slices scans	k = −15→15
18184 measured reflections	l = −18→17
6665 independent 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.102	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0483P)^2] where P = (Fo^2 + 2Fc^2)/3
6665 reflections	(Δ/σ)max = 0.001
363 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.44 e Å^−3

Special details

Experimental. ¹H NMR (CDCl₃, δ, p.p.m.): 5.84 (1H, s, C═CH), 4.31 (2H, br s, NCH₂), 3.76 (2H, br s, NCH₂), 2.57 (2H, t, J = 7.5 Hz, CH₂C═N), 1.74 (6H, br s, 3CH₂), 1.67 (2H, sextet, CH₃), 0.97 (3H, t, J = 7.4 Hz, CH₂CH₃); ¹³C NMR (CDCl₃, δ, p.p.m.): 13.7, 21.3, 23.9, 25.4, 26.2, 31.0, 48.5, 51.0, 92.5, 146.8, 151.0, 157.3.

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

7.9005 (0.0055) x - 2.5725 (0.0098) y + 5.8302 (0.0133) z = 5.3100 (0.0107)

* -0.0277 (0.0005) C13 * 0.0564 (0.0010) N6 * -0.0562 (0.0010) C19 * 0.0275 (0.0005) N5 0.4991 (0.0026) S2 - 0.2447 (0.0029) O6

Rms deviation of fitted atoms = 0.0443

9.2385 (0.0023) x + 0.9411 (0.0101) y + 4.0589 (0.0153) z = 3.6532 (0.0072)

Angle to previous plane (with approximate e.s.d.) = 20.19 (0.09)

* -0.0244 (0.0005) N1 * 0.0493 (0.0010) C7 * -0.0498 (0.0010) N2 * 0.0249 (0.0005) C1 - 0.5592 (0.0026) S1 0.2240 (0.0029) O3

Rms deviation of fitted atoms = 0.0391

7.7007 (0.0048) x - 2.3508 (0.0116) y + 7.5469 (0.0124) z = 6.7588 (0.0108)

Angle to previous plane (with approximate e.s.d.) = 25.16 (0.09)

* -0.0036 (0.0006) C14 * 0.0060 (0.0009) C13 * -0.0059 (0.0009) N6 * 0.0035 (0.0006) N7

Rms deviation of fitted atoms = 0.0049

7.7426 (0.0039) x - 2.2016 (0.0116) y + 7.6799 (0.0128) z = 6.8961 (0.0130)

Angle to previous plane (with approximate e.s.d.) = 0.88 (0.14)

* -0.0012 (0.0005) O6 * 0.0024 (0.0009) C13 * -0.0024 (0.0010) N6 * 0.0012 (0.0005) C19

Rms deviation of fitted atoms = 0.0019

8.9830 (0.0043) x + 0.5539 (0.0123) y + 2.0006 (0.0146) z = 2.6640 (0.0110)

Angle to previous plane (with approximate e.s.d.) = 31.72 (0.09)

* 0.0083 (0.0009) N2 * -0.0085 (0.0010) C1 * -0.0050 (0.0006) N3 * 0.0052 (0.0006) C2

Rms deviation of fitted atoms = 0.0070

9.0126 (0.0043) x + 0.5805 (0.0121) y + 2.1855 (0.0140) z = 2.7478 (0.0129)

Angle to previous plane (with approximate e.s.d.) = 0.79 (0.12)

* -0.0019 (0.0005) C7 * 0.0039 (0.0010) N2 * -0.0039 (0.0010) C1 * 0.0019 (0.0005) O3

Rms deviation of fitted atoms = 0.0031

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
C1	0.17850 (19)	0.57720 (14)	0.36605 (13)	0.0178 (4)
C2	0.1986 (2)	0.48629 (15)	0.30769 (13)	0.0199 (4)
H2	0.1994	0.4078	0.3303	0.024*
C3	0.2185 (2)	0.53391 (14)	0.20444 (13)	0.0178 (4)
C4	0.2367 (2)	0.47276 (15)	0.10813 (14)	0.0241 (4)
H4A	0.2848	0.5139	0.0450	0.029*
H4B	0.1309	0.4819	0.1080	0.029*
C5	0.3370 (2)	0.33948 (16)	0.10005 (15)	0.0293 (5)
H5A	0.2935	0.2993	0.1655	0.035*
H5B	0.3293	0.3037	0.0410	0.035*
C6	0.5076 (2)	0.31467 (19)	0.08303 (17)	0.0405 (5)
H6A	0.5171	0.3448	0.1435	0.061*
H6B	0.5514	0.3552	0.0190	0.061*
H6C	0.5657	0.2278	0.0755	0.061*
C7	0.17194 (19)	0.78497 (14)	0.33884 (13)	0.0155 (4)
C8	0.1781 (2)	0.98772 (14)	0.31655 (13)	0.0204 (4)
H8A	0.1113	0.9937	0.3915	0.024*
H8B	0.1184	1.0508	0.2772	0.024*
C9	0.3284 (2)	1.00774 (16)	0.30660 (14)	0.0229 (4)
H9A	0.3844	0.9481	0.3500	0.028*
H9B	0.3019	1.0890	0.3331	0.028*
C10	0.4350 (2)	0.99546 (15)	0.19238 (13)	0.0216 (4)
H10A	0.5360	1.0020	0.1878	0.026*
H10B	0.3844	1.0613	0.1505	0.026*
C11	0.4661 (2)	0.87439 (15)	0.14774 (14)	0.0234 (4)
H11A	0.5272	0.8710	0.0718	0.028*
H11B	0.5308	0.8095	0.1830	0.028*
C12	0.3153 (2)	0.85237 (15)	0.16207 (13)	0.0206 (4)
H12A	0.2571	0.9098	0.1187	0.025*
H12B	0.3415	0.7699	0.1383	0.025*
C13	0.07253 (19)	0.11250 (14)	0.85739 (13)	0.0163 (4)
C14	0.1051 (2)	0.02139 (15)	0.79455 (13)	0.0186 (4)
H14	0.0685	−0.0443	0.8117	0.022*
C15	0.2066 (2)	0.04572 (14)	0.69668 (13)	0.0180 (4)
C16	0.2706 (2)	−0.02444 (15)	0.59642 (13)	0.0222 (4)
H16A	0.3594	−0.0021	0.5474	0.027*
H16B	0.1875	−0.0012	0.5634	0.027*
C17	0.3274 (2)	−0.16004 (15)	0.61085 (14)	0.0242 (4)
H17A	0.2424	−0.1820	0.6654	0.029*
H17B	0.3498	−0.1992	0.5441	0.029*
C18	0.4734 (2)	−0.20726 (17)	0.64273 (18)	0.0381 (5)
H18A	0.5596	−0.1892	0.5875	0.057*
H18B	0.5034	−0.2945	0.6526	0.057*
H18C	0.4522	−0.1687	0.7087	0.057*
C19	0.13916 (19)	0.29273 (14)	0.84172 (13)	0.0151 (4)
C20	0.2128 (2)	0.38914 (15)	0.66457 (13)	0.0199 (4)
H20A	0.1380	0.4663	0.6494	0.024*
H20B	0.1969	0.3230	0.6382	0.024*
C21	0.3797 (2)	0.38526 (15)	0.60995 (14)	0.0253 (4)
H21A	0.3992	0.3957	0.5333	0.030*
H21B	0.4542	0.3059	0.6215	0.030*
C22	0.4078 (2)	0.48402 (16)	0.65205 (15)	0.0279 (5)
H22A	0.3450	0.5633	0.6308	0.033*
H22B	0.5204	0.4748	0.6208	0.033*
C23	0.3625 (2)	0.47952 (16)	0.77182 (15)	0.0294 (5)
H23A	0.4380	0.4068	0.7924	0.035*
H23B	0.3692	0.5507	0.7973	0.035*
C24	0.1969 (2)	0.47732 (15)	0.82328 (14)	0.0245 (4)
H24A	0.1740	0.4673	0.9003	0.029*
H24B	0.1196	0.5543	0.8103	0.029*
N1	0.11644 (17)	0.80440 (12)	0.44248 (10)	0.0185 (3)
N2	0.18862 (16)	0.67496 (11)	0.30195 (10)	0.0157 (3)
N3	0.21167 (17)	0.64692 (12)	0.19956 (11)	0.0179 (3)
N4	0.21523 (16)	0.86757 (12)	0.27451 (10)	0.0171 (3)
N5	0.07921 (17)	0.31059 (12)	0.94519 (11)	0.0198 (3)
N6	0.14981 (16)	0.18861 (11)	0.80067 (10)	0.0150 (3)
N7	0.23691 (16)	0.14388 (12)	0.69911 (10)	0.0170 (3)
N8	0.18317 (17)	0.37674 (12)	0.77919 (10)	0.0174 (3)
O1	−0.11454 (14)	0.73368 (10)	0.51039 (9)	0.0227 (3)
O2	0.04558 (15)	0.71855 (11)	0.62010 (9)	0.0256 (3)
O3	0.15326 (14)	0.58445 (10)	0.47088 (9)	0.0210 (3)
O4	−0.07925 (17)	0.25077 (11)	1.11407 (9)	0.0337 (4)
O5	0.18914 (16)	0.11424 (11)	1.03030 (10)	0.0305 (3)
O6	−0.02125 (14)	0.13982 (10)	0.95931 (9)	0.0203 (3)
S2	0.04843 (6)	0.20434 (4)	1.02092 (3)	0.02129 (12)
S1	0.03367 (5)	0.71953 (4)	0.51880 (3)	0.01814 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0157 (9)	0.0168 (8)	0.0170 (9)	−0.0045 (7)	−0.0033 (7)	0.0033 (7)
C2	0.0194 (9)	0.0144 (8)	0.0238 (10)	−0.0059 (7)	−0.0048 (8)	0.0000 (7)
C3	0.0160 (9)	0.0160 (8)	0.0212 (9)	−0.0050 (7)	−0.0055 (7)	−0.0025 (7)
C4	0.0300 (11)	0.0203 (9)	0.0257 (10)	−0.0102 (8)	−0.0106 (9)	−0.0046 (8)
C5	0.0340 (12)	0.0241 (10)	0.0299 (11)	−0.0110 (9)	−0.0073 (9)	−0.0078 (8)
C6	0.0324 (13)	0.0457 (13)	0.0397 (13)	−0.0051 (10)	−0.0093 (10)	−0.0219 (10)
C7	0.0150 (9)	0.0149 (8)	0.0180 (9)	−0.0054 (7)	−0.0061 (7)	−0.0023 (7)
C8	0.0246 (10)	0.0144 (8)	0.0199 (9)	−0.0076 (7)	−0.0024 (8)	−0.0043 (7)
C9	0.0283 (11)	0.0219 (9)	0.0239 (10)	−0.0127 (8)	−0.0099 (8)	−0.0025 (8)
C10	0.0225 (10)	0.0204 (9)	0.0243 (10)	−0.0099 (8)	−0.0076 (8)	−0.0005 (8)
C11	0.0244 (10)	0.0187 (9)	0.0231 (10)	−0.0075 (8)	−0.0026 (8)	−0.0017 (8)
C12	0.0284 (11)	0.0198 (9)	0.0131 (9)	−0.0110 (8)	−0.0028 (8)	−0.0016 (7)
C13	0.0168 (9)	0.0177 (8)	0.0156 (9)	−0.0084 (7)	−0.0053 (7)	0.0025 (7)
C14	0.0229 (10)	0.0175 (8)	0.0172 (9)	−0.0108 (7)	−0.0048 (8)	0.0007 (7)
C15	0.0202 (9)	0.0139 (8)	0.0197 (9)	−0.0043 (7)	−0.0086 (8)	0.0013 (7)
C16	0.0283 (11)	0.0223 (9)	0.0156 (9)	−0.0088 (8)	−0.0057 (8)	−0.0037 (7)
C17	0.0250 (11)	0.0226 (9)	0.0250 (10)	−0.0083 (8)	−0.0057 (8)	−0.0077 (8)
C18	0.0372 (13)	0.0276 (11)	0.0517 (14)	−0.0034 (9)	−0.0224 (11)	−0.0099 (10)
C19	0.0155 (9)	0.0127 (8)	0.0177 (9)	−0.0048 (7)	−0.0065 (7)	0.0000 (7)
C20	0.0295 (11)	0.0158 (8)	0.0169 (9)	−0.0095 (8)	−0.0103 (8)	0.0043 (7)
C21	0.0265 (11)	0.0216 (9)	0.0203 (10)	−0.0068 (8)	−0.0024 (8)	0.0051 (8)
C22	0.0201 (10)	0.0271 (10)	0.0359 (12)	−0.0129 (8)	−0.0075 (9)	0.0119 (9)
C23	0.0392 (12)	0.0239 (10)	0.0390 (12)	−0.0200 (9)	−0.0224 (10)	0.0086 (9)
C24	0.0381 (12)	0.0188 (9)	0.0203 (10)	−0.0161 (8)	−0.0071 (9)	−0.0008 (8)
N1	0.0228 (8)	0.0198 (7)	0.0133 (7)	−0.0097 (6)	−0.0040 (6)	−0.0004 (6)
N2	0.0199 (8)	0.0133 (7)	0.0133 (7)	−0.0063 (6)	−0.0048 (6)	0.0012 (6)
N3	0.0225 (8)	0.0174 (7)	0.0148 (7)	−0.0074 (6)	−0.0063 (6)	−0.0024 (6)
N4	0.0206 (8)	0.0143 (7)	0.0153 (7)	−0.0069 (6)	−0.0032 (6)	−0.0017 (6)
N5	0.0302 (9)	0.0160 (7)	0.0145 (7)	−0.0110 (6)	−0.0060 (7)	0.0009 (6)
N6	0.0176 (8)	0.0131 (7)	0.0136 (7)	−0.0067 (6)	−0.0032 (6)	0.0001 (6)
N7	0.0203 (8)	0.0164 (7)	0.0124 (7)	−0.0052 (6)	−0.0040 (6)	−0.0018 (6)
N8	0.0238 (8)	0.0153 (7)	0.0146 (7)	−0.0101 (6)	−0.0051 (6)	0.0017 (6)
O1	0.0181 (7)	0.0255 (7)	0.0225 (7)	−0.0080 (5)	−0.0038 (5)	−0.0001 (5)
O2	0.0328 (8)	0.0299 (7)	0.0136 (6)	−0.0116 (6)	−0.0070 (6)	0.0016 (5)
O3	0.0251 (7)	0.0166 (6)	0.0153 (6)	−0.0029 (5)	−0.0054 (5)	0.0024 (5)
O4	0.0523 (9)	0.0265 (7)	0.0169 (7)	−0.0215 (7)	0.0046 (6)	−0.0045 (6)
O5	0.0422 (9)	0.0255 (7)	0.0300 (7)	−0.0136 (6)	−0.0213 (7)	0.0111 (6)
O6	0.0248 (7)	0.0208 (6)	0.0148 (6)	−0.0124 (5)	−0.0008 (5)	−0.0016 (5)
S2	0.0339 (3)	0.0179 (2)	0.0140 (2)	−0.0135 (2)	−0.0059 (2)	0.00145 (18)
S1	0.0202 (2)	0.0180 (2)	0.0142 (2)	−0.00651 (18)	−0.00382 (18)	0.00074 (17)

Geometric parameters (Å, º)

S1—O1	1.4248 (13)	C9—C10	1.521 (2)
S1—O2	1.4161 (12)	C9—H9A	0.9900
S1—O3	1.6511 (12)	C9—H9B	0.9900
S1—N1	1.5845 (13)	C10—C11	1.526 (2)
N1—C7	1.334 (2)	C10—H10A	0.9900
N2—C7	1.401 (2)	C10—H10B	0.9900
N3—C3	1.325 (2)	C11—C12	1.521 (2)
C1—C2	1.342 (2)	C11—H11A	0.9900
O3—C1	1.364 (2)	C11—H11B	0.9900
N2—N3	1.3908 (18)	C12—N4	1.484 (2)
N2—C1	1.381 (2)	C12—H12A	0.9900
C2—C3	1.420 (2)	C12—H12B	0.9900
C2—H2	0.9500	C14—H14	0.9500
S2—O4	1.4168 (13)	C15—C16	1.499 (2)
S2—O5	1.4253 (13)	C16—C17	1.520 (2)
S2—O6	1.6410 (13)	C16—H16A	0.9900
S2—N5	1.5825 (13)	C16—H16B	0.9900
C13—C14	1.344 (2)	C17—C18	1.509 (3)
O6—C13	1.363 (2)	C17—H17A	0.9900
N6—C13	1.383 (2)	C17—H17B	0.9900
C14—C15	1.420 (2)	C18—H18A	0.9800
N5—C19	1.329 (2)	C18—H18B	0.9800
N6—N7	1.3901 (18)	C18—H18C	0.9800
N6—C19	1.383 (2)	C19—N8	1.329 (2)
N7—C15	1.320 (2)	C20—N8	1.477 (2)
C3—C4	1.502 (2)	C20—C21	1.510 (2)
C4—C5	1.523 (2)	C20—H20A	0.9900
C4—H4A	0.9900	C20—H20B	0.9900
C4—H4B	0.9900	C21—C22	1.522 (3)
C5—C6	1.503 (3)	C21—H21A	0.9900
C5—H5A	0.9900	C21—H21B	0.9900
C5—H5B	0.9900	C22—C23	1.527 (3)
C6—H6A	0.9800	C22—H22A	0.9900
C6—H6B	0.9800	C22—H22B	0.9900
C6—H6C	0.9800	C23—C24	1.518 (3)
C7—N4	1.324 (2)	C23—H23A	0.9900
C8—N4	1.484 (2)	C23—H23B	0.9900
C8—C9	1.520 (2)	C24—N8	1.477 (2)
C8—H8A	0.9900	C24—H24A	0.9900
C8—H8B	0.9900	C24—H24B	0.9900
C2—C1—O3	130.96 (14)	C18—C17—C16	112.83 (15)
C2—C1—N2	109.13 (14)	C18—C17—H17A	109.0
O3—C1—N2	119.91 (14)	C16—C17—H17A	109.0
C1—C2—C3	104.37 (14)	C18—C17—H17B	109.0
C1—C2—H2	127.8	C16—C17—H17B	109.0
C3—C2—H2	127.8	H17A—C17—H17B	107.8
N3—C3—C2	112.55 (15)	C17—C18—H18A	109.5
N3—C3—C4	120.14 (15)	C17—C18—H18B	109.5
C2—C3—C4	127.23 (15)	H18A—C18—H18B	109.5
C3—C4—C5	114.15 (15)	C17—C18—H18C	109.5
C3—C4—H4A	108.7	H18A—C18—H18C	109.5
C5—C4—H4A	108.7	H18B—C18—H18C	109.5
C3—C4—H4B	108.7	N5—C19—N8	119.53 (14)
C5—C4—H4B	108.7	N5—C19—N6	119.34 (14)
H4A—C4—H4B	107.6	N8—C19—N6	121.09 (14)
C6—C5—C4	113.83 (16)	N8—C20—C21	109.26 (14)
C6—C5—H5A	108.8	N8—C20—H20A	109.8
C4—C5—H5A	108.8	C21—C20—H20A	109.8
C6—C5—H5B	108.8	N8—C20—H20B	109.8
C4—C5—H5B	108.8	C21—C20—H20B	109.8
H5A—C5—H5B	107.7	H20A—C20—H20B	108.3
C5—C6—H6A	109.5	C20—C21—C22	110.57 (15)
C5—C6—H6B	109.5	C20—C21—H21A	109.5
H6A—C6—H6B	109.5	C22—C21—H21A	109.5
C5—C6—H6C	109.5	C20—C21—H21B	109.5
H6A—C6—H6C	109.5	C22—C21—H21B	109.5
H6B—C6—H6C	109.5	H21A—C21—H21B	108.1
N4—C7—N1	119.31 (14)	C21—C22—C23	111.41 (14)
N4—C7—N2	122.13 (15)	C21—C22—H22A	109.3
N1—C7—N2	118.51 (14)	C23—C22—H22A	109.3
N4—C8—C9	110.52 (14)	C21—C22—H22B	109.3
N4—C8—H8A	109.5	C23—C22—H22B	109.3
C9—C8—H8A	109.5	H22A—C22—H22B	108.0
N4—C8—H8B	109.5	C24—C23—C22	111.48 (15)
C9—C8—H8B	109.5	C24—C23—H23A	109.3
H8A—C8—H8B	108.1	C22—C23—H23A	109.3
C8—C9—C10	110.48 (15)	C24—C23—H23B	109.3
C8—C9—H9A	109.6	C22—C23—H23B	109.3
C10—C9—H9A	109.6	H23A—C23—H23B	108.0
C8—C9—H9B	109.6	N8—C24—C23	109.45 (15)
C10—C9—H9B	109.6	N8—C24—H24A	109.8
H9A—C9—H9B	108.1	C23—C24—H24A	109.8
C9—C10—C11	110.16 (14)	N8—C24—H24B	109.8
C9—C10—H10A	109.6	C23—C24—H24B	109.8
C11—C10—H10A	109.6	H24A—C24—H24B	108.2
C9—C10—H10B	109.6	C7—N1—S1	119.67 (12)
C11—C10—H10B	109.6	C1—N2—N3	109.40 (13)
H10A—C10—H10B	108.1	C1—N2—C7	123.45 (14)
C12—C11—C10	112.72 (14)	N3—N2—C7	127.12 (13)
C12—C11—H11A	109.0	C3—N3—N2	104.53 (13)
C10—C11—H11A	109.0	C7—N4—C8	119.74 (13)
C12—C11—H11B	109.0	C7—N4—C12	127.53 (14)
C10—C11—H11B	109.0	C8—N4—C12	112.41 (12)
H11A—C11—H11B	107.8	C19—N5—S2	119.72 (12)
N4—C12—C11	109.96 (14)	C13—N6—C19	123.67 (14)
N4—C12—H12A	109.7	C13—N6—N7	109.65 (13)
C11—C12—H12A	109.7	C19—N6—N7	126.68 (13)
N4—C12—H12B	109.7	C15—N7—N6	104.31 (13)
C11—C12—H12B	109.7	C19—N8—C20	127.41 (14)
H12A—C12—H12B	108.2	C19—N8—C24	120.63 (14)
C14—C13—O6	131.57 (15)	C20—N8—C24	111.83 (12)
C14—C13—N6	108.85 (14)	C1—O3—S1	111.55 (10)
O6—C13—N6	119.55 (14)	C13—O6—S2	112.17 (10)
C13—C14—C15	104.23 (14)	O4—S2—O5	118.47 (8)
C13—C14—H14	127.9	O4—S2—N5	110.26 (8)
C15—C14—H14	127.9	O5—S2—N5	113.23 (8)
N7—C15—C14	112.93 (15)	O4—S2—O6	103.73 (8)
N7—C15—C16	120.59 (15)	O5—S2—O6	105.85 (7)
C14—C15—C16	126.42 (15)	N5—S2—O6	103.60 (7)
C15—C16—C17	114.11 (14)	O2—S1—O1	118.86 (7)
C15—C16—H16A	108.7	O2—S1—N1	110.39 (8)
C17—C16—H16A	108.7	O1—S1—N1	113.54 (7)
C15—C16—H16B	108.7	O2—S1—O3	103.91 (7)
C17—C16—H16B	108.7	O1—S1—O3	105.73 (7)
H16A—C16—H16B	107.6	N1—S1—O3	102.41 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12B···N3	0.99	2.19	2.914 (2)	129
C20—H20B···N7	0.99	2.14	2.851 (2)	127