Structural characterization of the az­oxy derivative of an anti­tubercular 8-nitro-1,3-benzo­thia­zin-4-one

The crystal and mol­ecular structures of the az­oxy derivative of the anti­tubercular agent 8-nitro-2-(piperidin-1-yl)-6-(tri­fluoro­meth­yl)-4H-benzo[e][1,3]thia­zin-4-one are reported.

Computing details

Data collection: APEX4 (Bruker, 2017); cell refinement: SAINT (Bruker, 2019); data reduction: SAINT (Bruker, 2019); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: olex2.refine (Bourhis et al., 2015); molecular graphics: Mercury (Macrae et al., 2020) and OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

(Z)-1,2-Bis[4-oxo-2-(piperidin-1-yl)-6-(trifluoromethyl)-4H-benzo[e][1,3]thiazin-8-yl]diazene oxide

Crystal data

C28H24F6N6O3S2	F(000) = 1378.110
Mr = 670.66	Dx = 1.614 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 24.0754 (8) Å	Cell parameters from 9921 reflections
b = 6.3343 (2) Å	θ = 2.3–30.4°
c = 19.6822 (8) Å	µ = 0.28 mm^−1
β = 113.1511 (14)°	T = 100 K
V = 2759.84 (17) Å^3	Prism, yellow
Z = 4	0.06 × 0.05 × 0.03 mm

Data collection

Bruker AXS D8 Venture diffractometer	8391 independent reflections
Radiation source: IµS	7021 reflections with I ≥ 2u(I)
Incoatec Helios mirrors monochromator	Rint = 0.070
Detector resolution: 7.391 pixels mm^-1	θmax = 30.5°, θmin = 2.3°
φ– and ω–scans	h = −39→40
Absorption correction: gaussian (SADABS; Krause et al., 2015)	k = −10→10
Tmin = 0.990, Tmax = 0.996	l = −32→32
178787 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.030	Hydrogen site location: difference Fourier map
wR(F^2) = 0.080	All H-atom parameters refined
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0404P)^2 + 0.5834P] where P = (Fo^2 + 2Fc^2)/3
8391 reflections	(Δ/σ)max = 0.001
502 parameters	Δρmax = 0.51 e Å^−3
0 restraints	Δρmin = −0.41 e Å^−3
0 constraints

Special details

Experimental. Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C2	0.28147 (4)	1.62528 (16)	0.35880 (6)	0.01856 (18)
C4	0.18168 (5)	1.66757 (16)	0.27097 (6)	0.01990 (19)
C4A	0.18126 (4)	1.46289 (16)	0.23218 (5)	0.01821 (18)
C5	0.12727 (5)	1.41066 (17)	0.17388 (6)	0.02096 (19)
H5	0.0901 (6)	1.516 (2)	0.1592 (8)	0.032 (3)*
C6	0.12223 (4)	1.22486 (18)	0.13493 (6)	0.0215 (2)
C7	0.17143 (5)	1.09111 (17)	0.15219 (6)	0.02065 (19)
H7	0.1706 (7)	0.938 (2)	0.1223 (8)	0.034 (4)*
C8	0.22558 (4)	1.14234 (16)	0.20994 (5)	0.01785 (18)
C8A	0.23135 (4)	1.32656 (15)	0.25264 (5)	0.01688 (17)
C9	0.06319 (5)	1.1574 (2)	0.07626 (6)	0.0285 (2)
C10	0.38359 (5)	1.58701 (17)	0.45870 (6)	0.0233 (2)
H10a	0.3900 (6)	1.455 (2)	0.4242 (8)	0.032 (3)*
H10b	0.3783 (7)	1.516 (3)	0.5073 (9)	0.046 (4)*
C11	0.43872 (5)	1.72905 (19)	0.48551 (7)	0.0287 (2)
H11a	0.4441 (7)	1.795 (3)	0.4356 (9)	0.044 (4)*
H11b	0.4809 (8)	1.628 (3)	0.5181 (10)	0.054 (5)*
C12	0.43017 (5)	1.91406 (19)	0.52990 (7)	0.0284 (2)
H12a	0.4223 (7)	1.856 (2)	0.5775 (9)	0.045 (4)*
H12b	0.4717 (8)	2.017 (3)	0.5496 (9)	0.050 (4)*
C13	0.37393 (5)	2.03337 (17)	0.48121 (6)	0.0244 (2)
H13a	0.3795 (7)	2.092 (2)	0.4309 (9)	0.044 (4)*
H13b	0.3658 (7)	2.169 (2)	0.5094 (8)	0.042 (4)*
C14	0.31845 (5)	1.89287 (17)	0.45499 (7)	0.0245 (2)
H14a	0.3085 (7)	1.838 (3)	0.5017 (9)	0.049 (4)*
H14b	0.2788 (7)	1.972 (2)	0.4171 (8)	0.042 (4)*
F3	0.07072 (4)	1.02538 (16)	0.02812 (5)	0.0534 (3)
S1	0.297929 (11)	1.37714 (4)	0.329373 (14)	0.01863 (6)
N1	0.27597 (4)	0.99673 (14)	0.22486 (5)	0.01818 (16)
N2	0.32766 (4)	1.70422 (14)	0.41709 (5)	0.02082 (17)
N3	0.23098 (4)	1.73330 (14)	0.33002 (5)	0.02101 (17)
O1	0.13567 (3)	1.77651 (13)	0.24771 (5)	0.02728 (17)
O2	0.32334 (3)	1.03059 (13)	0.28039 (4)	0.02664 (17)
F1	0.02873 (3)	1.05970 (15)	0.10561 (5)	0.0451 (2)
F2	0.03113 (3)	1.32047 (13)	0.03808 (4)	0.03864 (18)
C2'	0.20796 (5)	0.37012 (16)	−0.00025 (6)	0.02017 (19)
C4'	0.29718 (5)	0.18587 (16)	0.07323 (6)	0.02048 (19)
C4A'	0.32046 (4)	0.35975 (16)	0.12869 (6)	0.01907 (18)
C5'	0.37853 (5)	0.33989 (18)	0.18380 (6)	0.0223 (2)
H5'	0.4033 (7)	0.204 (2)	0.1849 (8)	0.044 (4)*
C6'	0.40175 (5)	0.49576 (18)	0.23691 (6)	0.0229 (2)
C7'	0.36784 (5)	0.67241 (18)	0.23859 (6)	0.0218 (2)
H7'	0.3860 (6)	0.787 (2)	0.2804 (8)	0.034 (3)*
C8'	0.30904 (4)	0.69248 (16)	0.18499 (5)	0.01844 (18)
C8A'	0.28619 (4)	0.53676 (16)	0.12859 (5)	0.01775 (18)
C9'	0.46319 (5)	0.4618 (2)	0.29701 (7)	0.0313 (3)
C10'	0.11963 (5)	0.56488 (19)	−0.09017 (7)	0.0272 (2)
H10c	0.1317 (7)	0.647 (3)	−0.1305 (9)	0.051 (4)*
H10d	0.1259 (7)	0.666 (3)	−0.0433 (9)	0.046 (4)*
C11'	0.05376 (5)	0.4965 (2)	−0.12664 (7)	0.0288 (2)
H11c	0.0264 (8)	0.638 (3)	−0.1484 (10)	0.055 (5)*
H11d	0.0421 (8)	0.432 (3)	−0.0822 (10)	0.055 (5)*
C12'	0.04379 (6)	0.3354 (2)	−0.18782 (7)	0.0306 (2)
H12c	−0.0026 (7)	0.282 (3)	−0.2089 (9)	0.051 (4)*
H12d	0.0532 (7)	0.410 (3)	−0.2314 (9)	0.047 (4)*
C13'	0.08662 (5)	0.1495 (2)	−0.15767 (7)	0.0285 (2)
H13c	0.0763 (7)	0.070 (2)	−0.1158 (8)	0.040 (4)*
H13d	0.0819 (7)	0.034 (3)	−0.2003 (9)	0.047 (4)*
C14'	0.15169 (5)	0.2246 (2)	−0.12305 (7)	0.0326 (3)
H14c	0.1830 (8)	0.097 (3)	−0.0982 (10)	0.058 (5)*
H14d	0.1662 (7)	0.307 (3)	−0.1646 (9)	0.048 (4)*
N1'	0.26622 (4)	0.84787 (14)	0.17848 (5)	0.02021 (17)
N2'	0.15965 (4)	0.38055 (16)	−0.06438 (5)	0.0264 (2)
N3'	0.24492 (4)	0.20906 (14)	0.01250 (5)	0.02222 (18)
O1'	0.32738 (4)	0.02386 (12)	0.08251 (5)	0.02674 (17)
F1'	0.46238 (4)	0.29899 (17)	0.33958 (6)	0.0656 (3)
F2'	0.50496 (3)	0.42022 (16)	0.27055 (5)	0.0510 (2)
F3'	0.48340 (3)	0.62741 (14)	0.34161 (4)	0.04065 (19)
S1'	0.214168 (11)	0.58337 (4)	0.060830 (14)	0.01939 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.0182 (4)	0.0166 (4)	0.0206 (4)	−0.0010 (3)	0.0073 (4)	−0.0014 (3)
C4	0.0183 (4)	0.0184 (5)	0.0224 (5)	0.0012 (3)	0.0074 (4)	0.0007 (4)
C4A	0.0168 (4)	0.0189 (4)	0.0185 (4)	0.0009 (3)	0.0065 (4)	0.0003 (3)
C5	0.0168 (4)	0.0242 (5)	0.0197 (5)	0.0023 (4)	0.0049 (4)	−0.0002 (4)
C6	0.0164 (4)	0.0258 (5)	0.0193 (4)	0.0010 (4)	0.0037 (4)	−0.0027 (4)
C7	0.0173 (4)	0.0231 (5)	0.0187 (4)	0.0009 (4)	0.0040 (4)	−0.0030 (4)
C8	0.0161 (4)	0.0194 (4)	0.0167 (4)	−0.0004 (3)	0.0049 (4)	−0.0013 (3)
C8A	0.0163 (4)	0.0174 (4)	0.0165 (4)	0.0004 (3)	0.0059 (3)	0.0003 (3)
C9	0.0189 (5)	0.0349 (6)	0.0236 (5)	0.0025 (4)	−0.0002 (4)	−0.0064 (4)
C10	0.0216 (5)	0.0196 (5)	0.0256 (5)	0.0009 (4)	0.0059 (4)	−0.0030 (4)
C11	0.0210 (5)	0.0289 (6)	0.0319 (6)	0.0006 (4)	0.0058 (4)	−0.0100 (5)
C12	0.0245 (5)	0.0265 (5)	0.0281 (6)	0.0004 (4)	0.0037 (4)	−0.0077 (4)
C13	0.0270 (5)	0.0184 (5)	0.0255 (5)	−0.0004 (4)	0.0080 (4)	−0.0038 (4)
C14	0.0221 (5)	0.0219 (5)	0.0283 (5)	0.0003 (4)	0.0087 (4)	−0.0062 (4)
F3	0.0275 (4)	0.0711 (6)	0.0430 (5)	0.0112 (4)	−0.0060 (3)	−0.0325 (4)
S1	0.01677 (11)	0.01686 (11)	0.01941 (11)	0.00039 (8)	0.00407 (9)	−0.00168 (8)
N1	0.0181 (4)	0.0188 (4)	0.0167 (4)	0.0000 (3)	0.0059 (3)	−0.0013 (3)
N2	0.0188 (4)	0.0184 (4)	0.0236 (4)	−0.0001 (3)	0.0066 (3)	−0.0032 (3)
N3	0.0191 (4)	0.0189 (4)	0.0236 (4)	0.0009 (3)	0.0070 (3)	−0.0022 (3)
O1	0.0219 (4)	0.0233 (4)	0.0316 (4)	0.0060 (3)	0.0052 (3)	−0.0016 (3)
O2	0.0203 (4)	0.0250 (4)	0.0275 (4)	0.0034 (3)	0.0017 (3)	−0.0062 (3)
F1	0.0247 (4)	0.0540 (5)	0.0443 (5)	−0.0130 (3)	0.0005 (3)	0.0029 (4)
F2	0.0277 (4)	0.0455 (5)	0.0299 (4)	0.0071 (3)	−0.0024 (3)	0.0017 (3)
C2'	0.0196 (4)	0.0202 (5)	0.0210 (5)	0.0005 (4)	0.0082 (4)	−0.0040 (4)
C4'	0.0222 (5)	0.0180 (5)	0.0236 (5)	0.0022 (4)	0.0116 (4)	0.0004 (4)
C4A'	0.0185 (4)	0.0197 (4)	0.0198 (4)	0.0027 (4)	0.0084 (4)	0.0014 (4)
C5'	0.0195 (5)	0.0241 (5)	0.0236 (5)	0.0053 (4)	0.0088 (4)	0.0024 (4)
C6'	0.0177 (4)	0.0284 (5)	0.0207 (5)	0.0044 (4)	0.0055 (4)	0.0018 (4)
C7'	0.0178 (4)	0.0256 (5)	0.0196 (5)	0.0021 (4)	0.0047 (4)	−0.0016 (4)
C8'	0.0172 (4)	0.0206 (5)	0.0166 (4)	0.0008 (3)	0.0057 (4)	−0.0004 (3)
C8A'	0.0180 (4)	0.0185 (4)	0.0175 (4)	0.0011 (3)	0.0078 (4)	−0.0007 (3)
C9'	0.0208 (5)	0.0376 (6)	0.0294 (6)	0.0072 (5)	0.0033 (5)	0.0008 (5)
C10'	0.0273 (5)	0.0273 (5)	0.0219 (5)	0.0038 (4)	0.0041 (4)	−0.0051 (4)
C11'	0.0249 (5)	0.0316 (6)	0.0262 (5)	0.0075 (4)	0.0063 (4)	−0.0017 (5)
C12'	0.0249 (5)	0.0327 (6)	0.0277 (6)	0.0004 (5)	0.0031 (5)	−0.0053 (5)
C13'	0.0244 (5)	0.0290 (6)	0.0288 (6)	−0.0002 (4)	0.0069 (5)	−0.0085 (5)
C14'	0.0230 (5)	0.0381 (7)	0.0329 (6)	0.0021 (5)	0.0068 (5)	−0.0178 (5)
N1'	0.0214 (4)	0.0211 (4)	0.0177 (4)	0.0020 (3)	0.0073 (3)	−0.0030 (3)
N2'	0.0222 (4)	0.0290 (5)	0.0244 (5)	0.0040 (4)	0.0052 (4)	−0.0095 (4)
N3'	0.0223 (4)	0.0197 (4)	0.0248 (4)	0.0013 (3)	0.0093 (4)	−0.0043 (3)
O1'	0.0291 (4)	0.0196 (4)	0.0319 (4)	0.0058 (3)	0.0124 (3)	0.0006 (3)
F1'	0.0411 (5)	0.0661 (7)	0.0601 (6)	0.0001 (5)	−0.0119 (4)	0.0341 (5)
F2'	0.0201 (3)	0.0722 (6)	0.0523 (5)	0.0090 (4)	0.0053 (3)	−0.0254 (5)
F3'	0.0266 (4)	0.0545 (5)	0.0303 (4)	0.0095 (3)	−0.0002 (3)	−0.0110 (3)
S1'	0.01745 (11)	0.02073 (12)	0.01844 (11)	0.00258 (9)	0.00539 (9)	−0.00378 (9)

Geometric parameters (Å, º)

C2—S1	1.7730 (10)	N1—N1'	1.2685 (12)
C2—N2	1.3416 (13)	C2'—N2'	1.3402 (14)
C2—N3	1.3135 (13)	C2'—N3'	1.3115 (13)
C4—C4A	1.5026 (14)	C2'—S1'	1.7750 (10)
C4—N3	1.3595 (13)	C4'—C4A'	1.4958 (15)
C4—O1	1.2304 (12)	C4'—N3'	1.3604 (14)
C4A—C5	1.3938 (14)	C4'—O1'	1.2291 (12)
C4A—C8A	1.4074 (13)	C4A'—C5'	1.3981 (14)
C5—H5	1.063 (14)	C4A'—C8A'	1.3917 (13)
C5—C6	1.3837 (15)	C5'—H5'	1.041 (16)
C6—C7	1.3855 (14)	C5'—C6'	1.3858 (16)
C6—C9	1.4987 (15)	C6'—C7'	1.3931 (15)
C7—H7	1.129 (15)	C6'—C9'	1.5027 (15)
C7—C8	1.3899 (14)	C7'—H7'	1.053 (14)
C8—C8A	1.4127 (14)	C7'—C8'	1.3994 (14)
C8—N1	1.4589 (13)	C8'—C8A'	1.4240 (14)
C8A—S1	1.7461 (10)	C8'—N1'	1.3943 (13)
C9—F3	1.3284 (14)	C8A'—S1'	1.7475 (10)
C9—F1	1.3347 (15)	C9'—F1'	1.3336 (16)
C9—F2	1.3310 (14)	C9'—F2'	1.3280 (15)
C10—H10a	1.124 (14)	C9'—F3'	1.3313 (15)
C10—H10b	1.108 (16)	C10'—H10c	1.082 (16)
C10—C11	1.5162 (16)	C10'—H10d	1.082 (16)
C10—N2	1.4724 (13)	C10'—C11'	1.5239 (17)
C11—H11a	1.120 (16)	C10'—N2'	1.4712 (15)
C11—H11b	1.158 (18)	C11'—H11c	1.094 (17)
C11—C12	1.5234 (16)	C11'—H11d	1.098 (17)
C12—H12a	1.089 (15)	C11'—C12'	1.5240 (17)
C12—H12b	1.129 (17)	C12'—H12c	1.082 (16)
C12—C13	1.5173 (16)	C12'—H12d	1.080 (16)
C13—H13a	1.114 (16)	C12'—C13'	1.5231 (17)
C13—H13b	1.081 (15)	C13'—H13c	1.076 (15)
C13—C14	1.5168 (15)	C13'—H13d	1.086 (16)
C14—H14a	1.095 (16)	C13'—C14'	1.5182 (16)
C14—H14b	1.077 (16)	C14'—H14c	1.080 (18)
C14—N2	1.4709 (13)	C14'—H14d	1.135 (16)
N1—O2	1.2494 (11)	C14'—N2'	1.4740 (14)
N2—C2—S1	113.15 (7)	C4—N3—C2	123.92 (9)
N3—C2—S1	127.50 (8)	N3'—C2'—N2'	119.40 (9)
N3—C2—N2	119.35 (9)	S1'—C2'—N2'	114.27 (8)
N3—C4—C4A	121.86 (9)	S1'—C2'—N3'	126.32 (8)
O1—C4—C4A	118.01 (9)	N3'—C4'—C4A'	120.89 (9)
O1—C4—N3	120.13 (10)	O1'—C4'—C4A'	118.45 (10)
C5—C4A—C4	116.16 (9)	O1'—C4'—N3'	120.62 (10)
C8A—C4A—C4	123.38 (9)	C5'—C4A'—C4'	118.26 (9)
C8A—C4A—C5	120.45 (9)	C8A'—C4A'—C4'	122.71 (9)
H5—C5—C4A	119.2 (7)	C8A'—C4A'—C5'	119.01 (10)
C6—C5—C4A	120.55 (10)	H5'—C5'—C4A'	118.7 (8)
C6—C5—H5	120.3 (7)	C6'—C5'—C4A'	120.32 (10)
C7—C6—C5	120.27 (9)	C6'—C5'—H5'	120.9 (8)
C9—C6—C5	121.30 (10)	C7'—C6'—C5'	121.59 (10)
C9—C6—C7	118.36 (10)	C9'—C6'—C5'	118.16 (10)
H7—C7—C6	124.0 (8)	C9'—C6'—C7'	120.08 (10)
C8—C7—C6	119.63 (10)	H7'—C7'—C6'	120.2 (8)
C8—C7—H7	116.4 (8)	C8'—C7'—C6'	118.92 (10)
C8A—C8—C7	121.38 (9)	C8'—C7'—H7'	120.9 (8)
N1—C8—C7	117.09 (9)	C8A'—C8'—C7'	119.41 (9)
N1—C8—C8A	121.53 (8)	N1'—C8'—C7'	128.73 (9)
C8—C8A—C4A	117.63 (9)	N1'—C8'—C8A'	111.85 (8)
S1—C8A—C4A	121.80 (8)	C8'—C8A'—C4A'	120.65 (9)
S1—C8A—C8	120.55 (7)	S1'—C8A'—C4A'	123.16 (8)
F3—C9—C6	112.03 (9)	S1'—C8A'—C8'	116.19 (7)
F1—C9—C6	111.19 (10)	F1'—C9'—C6'	110.62 (10)
F1—C9—F3	107.41 (11)	F2'—C9'—C6'	112.50 (10)
F2—C9—C6	112.17 (10)	F2'—C9'—F1'	107.08 (11)
F2—C9—F3	107.29 (10)	F3'—C9'—C6'	113.43 (10)
F2—C9—F1	106.44 (10)	F3'—C9'—F1'	106.67 (11)
H10b—C10—H10a	108.0 (11)	F3'—C9'—F2'	106.14 (10)
C11—C10—H10a	109.9 (7)	H10d—C10'—H10c	110.6 (12)
C11—C10—H10b	108.8 (8)	C11'—C10'—H10c	108.7 (9)
N2—C10—H10a	110.6 (7)	C11'—C10'—H10d	109.9 (8)
N2—C10—H10b	107.1 (8)	N2'—C10'—H10c	108.0 (9)
N2—C10—C11	112.23 (9)	N2'—C10'—H10d	108.7 (8)
H11a—C11—C10	107.7 (8)	N2'—C10'—C11'	110.86 (10)
H11b—C11—C10	108.8 (9)	H11c—C11'—C10'	107.8 (9)
H11b—C11—H11a	108.3 (12)	H11d—C11'—C10'	106.0 (9)
C12—C11—C10	111.03 (10)	H11d—C11'—H11c	108.3 (12)
C12—C11—H11a	107.6 (8)	C12'—C11'—C10'	111.95 (10)
C12—C11—H11b	113.2 (9)	C12'—C11'—H11c	110.9 (9)
H12a—C12—C11	110.1 (8)	C12'—C11'—H11d	111.6 (9)
H12b—C12—C11	110.0 (9)	H12c—C12'—C11'	109.3 (9)
H12b—C12—H12a	109.3 (12)	H12d—C12'—C11'	108.4 (8)
C13—C12—C11	108.02 (9)	H12d—C12'—H12c	109.8 (12)
C13—C12—H12a	107.2 (8)	C13'—C12'—C11'	109.74 (10)
C13—C12—H12b	112.2 (9)	C13'—C12'—H12c	110.4 (9)
H13a—C13—C12	109.9 (8)	C13'—C12'—H12d	109.2 (8)
H13b—C13—C12	111.6 (8)	H13c—C13'—C12'	109.7 (8)
H13b—C13—H13a	107.4 (11)	H13d—C13'—C12'	111.8 (9)
C14—C13—C12	111.74 (9)	H13d—C13'—H13c	106.8 (12)
C14—C13—H13a	106.9 (8)	C14'—C13'—C12'	110.73 (11)
C14—C13—H13b	109.2 (8)	C14'—C13'—H13c	108.1 (8)
H14a—C14—C13	110.8 (9)	C14'—C13'—H13d	109.5 (8)
H14b—C14—C13	112.7 (8)	H14c—C14'—C13'	112.5 (9)
H14b—C14—H14a	107.6 (12)	H14d—C14'—C13'	112.1 (8)
N2—C14—C13	111.16 (9)	H14d—C14'—H14c	108.1 (12)
N2—C14—H14a	107.1 (9)	N2'—C14'—C13'	110.78 (9)
N2—C14—H14b	107.2 (8)	N2'—C14'—H14c	107.0 (9)
C8A—S1—C2	101.43 (5)	N2'—C14'—H14d	106.0 (8)
O2—N1—C8	117.93 (8)	C8'—N1'—N1	122.53 (9)
N1'—N1—C8	114.91 (8)	C10'—N2'—C2'	124.91 (9)
N1'—N1—O2	127.16 (9)	C14'—N2'—C2'	120.14 (9)
C10—N2—C2	123.85 (9)	C14'—N2'—C10'	113.32 (9)
C14—N2—C2	119.79 (9)	C4'—N3'—C2'	125.14 (9)
C14—N2—C10	114.52 (8)	C8A'—S1'—C2'	100.51 (5)
C2—N2—C10—C11	144.51 (11)	N1—N1'—C8'—C7'	−1.88 (12)
C2—N2—C14—C13	−143.83 (10)	N1—N1'—C8'—C8A'	176.68 (10)
C2—N3—C4—C4A	−0.99 (12)	C2'—N2'—C10'—C11'	−139.53 (12)
C2—N3—C4—O1	179.08 (10)	C2'—N2'—C14'—C13'	136.81 (12)
C4—C4A—C5—C6	−179.66 (9)	C2'—N3'—C4'—C4A'	−6.44 (12)
C4—C4A—C8A—C8	−177.90 (9)	C2'—N3'—C4'—O1'	175.95 (11)
C4—C4A—C8A—S1	3.77 (11)	C4'—C4A'—C5'—C6'	−179.23 (9)
C4A—C5—C6—C7	−1.77 (12)	C4'—C4A'—C8A'—C8'	176.45 (9)
C4A—C5—C6—C9	174.91 (10)	C4'—C4A'—C8A'—S1'	−3.91 (11)
C4A—C8A—C8—C7	−3.38 (11)	C4A'—C5'—C6'—C7'	1.93 (12)
C4A—C8A—C8—N1	177.15 (8)	C4A'—C5'—C6'—C9'	177.12 (10)
C5—C6—C7—C8	1.37 (12)	C4A'—C8A'—C8'—C7'	3.52 (11)
C5—C6—C9—F3	156.95 (12)	C4A'—C8A'—C8'—N1'	−175.19 (10)
C5—C6—C9—F1	−82.85 (11)	C5'—C6'—C7'—C8'	−0.29 (12)
C5—C6—C9—F2	36.21 (11)	C5'—C6'—C9'—F1'	−65.33 (12)
C6—C7—C8—C8A	1.25 (12)	C5'—C6'—C9'—F2'	54.37 (11)
C6—C7—C8—N1	−179.25 (9)	C5'—C6'—C9'—F3'	174.86 (11)
C7—C8—C8A—S1	174.97 (8)	C6'—C7'—C8'—C8A'	−2.38 (12)
C7—C8—N1—O2	−174.00 (9)	C6'—C7'—C8'—N1'	176.08 (9)
C7—C8—N1—N1'	6.35 (11)	C7'—C8'—C8A'—S1'	−176.14 (8)
C8—N1—N1'—C8'	−178.86 (8)	C10'—C11'—C12'—C13'	54.26 (12)
C10—C11—C12—C13	−57.50 (11)	C10'—N2'—C14'—C13'	−57.05 (11)
C10—N2—C14—C13	51.03 (10)	C11'—C12'—C13'—C14'	−55.55 (12)
C11—C12—C13—C14	58.50 (11)	C12'—C13'—C14'—N2'	56.80 (11)
C12—C13—C14—N2	−55.30 (10)