N-Iso­propyl-N-[(E)-2-phenyl­propenyl]­thio­benz­amide and N-iso­propyl-3-methoxy-N-[(E)-2-phenyl­propenyl]­thio­benz­amide

The crystal structures of the two title thio­benz­amides, C₁₉H₂₁NS, (I), and C₂₀H₂₃NOS, (II), were determined to investigate the relationship between the photoreactivity in solid state and the structure. Their geometry was confirmed to be the E isomer in each case.

S1. Experimental

The title compounds, (I) and (II), were prepared by one of the authors (HA) in a study on photocyclization of enamides and thioamides in the solid state (Aoyama, 2000). Crystals were grown from hexane solutions.

S2. Refinement

X-ray intensity data were measured for ±h,+k,-l (θ < 75°) and ±h,-k,-l (θ < 30°) of (I), and for -h,+k,±l (θ < 75°) and -h,-k,±l (θ < 30°) of (II). The completeness of symmetry unique reflections (θ < 75°) was 92.7% for both (I) and (II), which was due to the blind region of the low-temperature apparatus. All H atoms were located from difference syntheses and refined isotropically. The C—H bond distances are 0.92 (3)—1.13 (3) Å in (I) and 0.89 (2)—1.01 (3) Å in (II).

Computing details

For both compounds, data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: TEXSAN.

(I) N-Isopropyl-N-{(E)-2-phenyl-propenyl}-thiobenzamide

Crystal data

C19H21NS	Dx = 1.173 Mg m^−3
Mr = 295.44	Cu Kα radiation, λ = 1.54184 Å
Monoclinic, C2/c	Cell parameters from 25 reflections
a = 17.479 (3) Å	θ = 29.4–30.0°
b = 9.100 (2) Å	µ = 1.64 mm^−1
c = 21.494 (3) Å	T = 248 K
β = 101.94 (1)°	Plate-like, yellow
V = 3344.7 (11) Å^3	0.6 × 0.4 × 0.3 mm
Z = 8

Data collection

Rigaku AFC-7R diffractometer	Rint = 0.055
θ–2θ scans	θmax = 75.0°, θmin = 2.5°
Absorption correction: integration (Coppens et al., 1965)	h = −22→22
Tmin = 0.459, Tmax = 0.651	k = −5→11
3812 measured reflections	l = −27→0
3210 independent reflections	3 standard reflections every 150 reflections
2923 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.046	w = 1/[σ^2(Fo^2) + (0.0773P)^2 + 2.6174P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.134	(Δ/σ)max = 0.001
S = 1.06	Δρmax = 0.30 e Å^−3
3210 reflections	Δρmin = −0.42 e Å^−3
274 parameters

Special details

Refinement. Refinement was based on F² against all reflections. The weighted R-factor (wR) and goodness of fit (S) were based on F², and conventional R-factor (R) was calculated on F, with F set to zero for negative F². The threshold expression of I > 2σ(I) was used only for calculating R-factor(gt).

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

	x	y	z	Uiso*/Ueq
S1	0.37936 (3)	0.87577 (5)	0.98318 (2)	0.0482 (2)
N2	0.42952 (8)	0.7972 (2)	0.87891 (6)	0.0359 (3)
C3	0.39478 (9)	0.7598 (2)	0.92707 (7)	0.0341 (3)
C4	0.3734 (1)	0.6020 (2)	0.93112 (7)	0.0346 (3)
C5	0.2985 (1)	0.5610 (2)	0.93709 (9)	0.0454 (4)
C6	0.2812 (1)	0.4140 (3)	0.9432 (1)	0.0559 (5)
C7	0.3379 (2)	0.3076 (2)	0.9454 (1)	0.0596 (6)
C8	0.4124 (2)	0.3480 (2)	0.9411 (1)	0.0551 (5)
C9	0.4304 (1)	0.4940 (2)	0.93280 (8)	0.0428 (4)
C10	0.4681 (1)	0.9420 (2)	0.87672 (9)	0.0454 (4)
C11	0.4180 (2)	1.0423 (3)	0.8292 (1)	0.0652 (6)
C12	0.5497 (2)	0.9206 (3)	0.8639 (1)	0.0651 (6)
C13	0.4254 (1)	0.7040 (2)	0.82441 (7)	0.0348 (3)
C14	0.3596 (1)	0.6778 (2)	0.78232 (7)	0.0352 (4)
C15	0.2817 (1)	0.7419 (3)	0.7855 (1)	0.0584 (6)
C16	0.36245 (9)	0.5752 (2)	0.72909 (7)	0.0349 (4)
C17	0.3264 (2)	0.6099 (3)	0.66685 (9)	0.0570 (5)
C18	0.3320 (2)	0.5152 (3)	0.6174 (1)	0.0708 (7)
C19	0.3714 (1)	0.3848 (3)	0.6288 (1)	0.0636 (7)
C20	0.4047 (1)	0.3469 (3)	0.6905 (1)	0.0584 (5)
C21	0.4004 (1)	0.4416 (2)	0.74028 (9)	0.0446 (4)
H5	0.260 (1)	0.639 (3)	0.936 (1)	0.05464 (8)*
H6	0.226 (2)	0.381 (3)	0.947 (1)	0.0828 (1)*
H7	0.326 (1)	0.204 (3)	0.950 (1)	0.06378 (9)*
H8	0.456 (2)	0.276 (3)	0.944 (1)	0.07639 (10)*
H9	0.482 (1)	0.517 (3)	0.932 (1)	0.05608 (8)*
H10	0.471 (1)	0.985 (3)	0.917 (1)	0.05508 (8)*
H11A	0.442 (1)	1.140 (3)	0.831 (1)	0.06411 (9)*
H11B	0.365 (2)	1.056 (3)	0.840 (1)	0.0846 (1)*
H11C	0.411 (2)	1.005 (3)	0.786 (1)	0.0777 (1)*
H12A	0.575 (2)	0.840 (4)	0.891 (2)	0.0843 (1)*
H12B	0.577 (2)	1.023 (3)	0.867 (1)	0.0803 (1)*
H12C	0.542 (2)	0.878 (3)	0.818 (2)	0.0878 (1)*
H13	0.477 (1)	0.661 (2)	0.819 (1)	0.05049 (7)*
H15A	0.283 (2)	0.816 (3)	0.822 (1)	0.07671 (10)*
H15B	0.244 (1)	0.648 (3)	0.796 (1)	0.05996 (8)*
H15C	0.257 (2)	0.789 (4)	0.749 (2)	0.0936 (1)*
H17	0.302 (2)	0.704 (4)	0.660 (1)	0.0828 (1)*
H18	0.305 (2)	0.547 (3)	0.577 (2)	0.0900 (1)*
H19	0.374 (2)	0.313 (3)	0.594 (1)	0.0778 (1)*
H20	0.431 (2)	0.252 (3)	0.699 (1)	0.0838 (1)*
H21	0.422 (1)	0.412 (3)	0.783 (1)	0.06118 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0755 (4)	0.0382 (3)	0.0371 (3)	0.0023 (2)	0.0259 (2)	−0.0068 (2)
N2	0.0483 (8)	0.0335 (7)	0.0279 (6)	−0.0047 (6)	0.0126 (6)	−0.0054 (5)
C3	0.0408 (8)	0.0338 (8)	0.0273 (7)	0.0033 (6)	0.0062 (6)	−0.0014 (6)
C4	0.0461 (9)	0.0335 (8)	0.0246 (7)	0.0002 (7)	0.0082 (6)	−0.0009 (6)
C5	0.051 (1)	0.049 (1)	0.0382 (9)	−0.0030 (8)	0.0146 (8)	−0.0023 (8)
C6	0.069 (1)	0.057 (1)	0.044 (1)	−0.021 (1)	0.0176 (9)	−0.0034 (9)
C7	0.098 (2)	0.038 (1)	0.042 (1)	−0.016 (1)	0.012 (1)	−0.0002 (8)
C8	0.080 (1)	0.0378 (9)	0.044 (1)	0.0107 (10)	0.0040 (10)	−0.0005 (8)
C9	0.052 (1)	0.0389 (9)	0.0362 (9)	0.0044 (8)	0.0057 (7)	−0.0011 (7)
C10	0.068 (1)	0.0362 (9)	0.0367 (9)	−0.0125 (8)	0.0209 (8)	−0.0079 (7)
C11	0.097 (2)	0.039 (1)	0.063 (1)	0.001 (1)	0.024 (1)	0.0053 (10)
C12	0.064 (1)	0.061 (1)	0.075 (2)	−0.022 (1)	0.024 (1)	−0.008 (1)
C13	0.0444 (9)	0.0338 (8)	0.0282 (7)	−0.0016 (7)	0.0126 (7)	−0.0050 (6)
C14	0.0433 (8)	0.0347 (8)	0.0281 (7)	0.0028 (7)	0.0087 (6)	−0.0013 (6)
C15	0.053 (1)	0.070 (1)	0.050 (1)	0.019 (1)	0.0047 (9)	−0.014 (1)
C16	0.0396 (8)	0.0391 (8)	0.0272 (7)	−0.0063 (7)	0.0096 (6)	−0.0053 (6)
C17	0.083 (2)	0.054 (1)	0.0299 (9)	−0.002 (1)	0.0019 (9)	0.0001 (8)
C18	0.101 (2)	0.082 (2)	0.0275 (9)	−0.019 (1)	0.008 (1)	−0.009 (1)
C19	0.067 (1)	0.080 (2)	0.050 (1)	−0.023 (1)	0.027 (1)	−0.035 (1)
C20	0.055 (1)	0.059 (1)	0.063 (1)	−0.0004 (10)	0.0191 (10)	−0.028 (1)
C21	0.0458 (9)	0.049 (1)	0.0393 (9)	0.0050 (8)	0.0087 (8)	−0.0107 (8)

Geometric parameters (Å, º)

S1—C3	1.666 (2)	C12—H12A	0.98 (3)
N2—C3	1.348 (2)	C12—H12B	1.05 (3)
N2—C10	1.486 (2)	C12—H12C	1.04 (3)
N2—C13	1.436 (2)	C13—C14	1.329 (2)
C3—C4	1.490 (2)	C13—H13	1.02 (2)
C4—C5	1.392 (3)	C14—C15	1.496 (3)
C4—C9	1.395 (3)	C14—C16	1.485 (2)
C5—C6	1.383 (3)	C15—H15A	1.02 (3)
C5—H5	0.97 (2)	C15—H15B	1.13 (3)
C6—C7	1.380 (3)	C15—H15C	0.92 (3)
C6—H6	1.02 (3)	C16—C17	1.392 (2)
C7—C8	1.375 (4)	C16—C21	1.382 (3)
C7—H7	0.98 (3)	C17—C18	1.388 (3)
C8—C9	1.385 (3)	C17—H17	0.95 (3)
C8—H8	0.99 (3)	C18—C19	1.368 (4)
C9—H9	0.93 (2)	C18—H18	0.95 (3)
C10—C11	1.508 (3)	C19—C20	1.376 (3)
C10—C12	1.520 (4)	C19—H19	1.01 (3)
C10—H10	0.93 (3)	C20—C21	1.389 (3)
C11—H11A	0.98 (3)	C20—H20	0.98 (3)
C11—H11B	1.00 (3)	C21—H21	0.95 (3)
C11—H11C	0.97 (3)
C3—N2—C10	121.9 (1)	C10—C12—H12A	108 (1)
C3—N2—C13	121.5 (1)	C10—C12—H12B	107 (1)
C10—N2—C13	116.4 (1)	C10—C12—H12C	105 (1)
S1—C3—N2	124.2 (1)	H12A—C12—H12B	118 (2)
S1—C3—C4	119.2 (1)	H12A—C12—H12C	103 (2)
N2—C3—C4	116.5 (1)	H12B—C12—H12C	111 (2)
C3—C4—C5	121.1 (2)	N2—C13—C14	123.5 (2)
C3—C4—C9	119.6 (2)	N2—C13—H13	115 (1)
C5—C4—C9	119.2 (2)	C14—C13—H13	120 (1)
C4—C5—C6	119.8 (2)	C13—C14—C15	124.5 (2)
C4—C5—H5	117 (1)	C13—C14—C16	118.4 (2)
C6—C5—H5	122 (1)	C15—C14—C16	117.1 (1)
C5—C6—C7	120.7 (2)	C14—C15—H15A	114 (1)
C5—C6—H6	121 (1)	C14—C15—H15B	106 (1)
C7—C6—H6	117 (1)	C14—C15—H15C	114 (2)
C6—C7—C8	119.7 (2)	H15A—C15—H15B	104 (2)
C6—C7—H7	120 (1)	H15A—C15—H15C	106 (2)
C8—C7—H7	119 (1)	H15B—C15—H15C	109 (2)
C7—C8—C9	120.5 (2)	C14—C16—C17	121.1 (2)
C7—C8—H8	122 (1)	C14—C16—C21	120.7 (1)
C9—C8—H8	116 (1)	C17—C16—C21	118.2 (2)
C4—C9—C8	120.0 (2)	C16—C17—C18	120.3 (2)
C4—C9—H9	121 (1)	C16—C17—H17	116 (1)
C8—C9—H9	117 (1)	C18—C17—H17	122 (1)
N2—C10—C11	110.7 (2)	C17—C18—C19	120.9 (2)
N2—C10—C12	110.0 (2)	C17—C18—H18	114 (2)
N2—C10—H10	106 (1)	C19—C18—H18	124 (2)
C11—C10—C12	112.9 (2)	C18—C19—C20	119.2 (2)
C11—C10—H10	106 (1)	C18—C19—H19	122 (1)
C12—C10—H10	110 (1)	C20—C19—H19	118 (1)
C10—C11—H11A	109 (1)	C19—C20—C21	120.4 (2)
C10—C11—H11B	110 (1)	C19—C20—H20	119 (1)
C10—C11—H11C	112 (1)	C21—C20—H20	119 (1)
H11A—C11—H11B	107 (2)	C16—C21—C20	120.8 (2)
H11A—C11—H11C	108 (2)	C16—C21—H21	119 (1)
H11B—C11—H11C	108 (2)	C20—C21—H21	119 (1)

(II) N-Isopropyl-3-methoxy-N-{(E)-2-phenyl-propenyl}-thiobenzamide

Crystal data

C20H23NOS	Dx = 1.169 Mg m^−3
Mr = 325.47	Cu Kα radiation, λ = 1.54184 Å
Monoclinic, C2/c	Cell parameters from 25 reflections
a = 19.483 (1) Å	θ = 27.3–29.4°
b = 9.111 (1) Å	µ = 1.57 mm^−1
c = 21.611 (2) Å	T = 248 K
β = 105.39 (1)°	Prism, yellow
V = 3698.7 (6) Å^3	0.4 × 0.3 × 0.3 mm
Z = 8

Data collection

Rigaku AFC-7R diffractometer	Rint = 0.028
θ–2θ scans	θmax = 75.0°, θmin = 2.5°
Absorption correction: integration (Coppens et al., 1965)	h = −24→0
Tmin = 0.546, Tmax = 0.689	k = −5→11
4076 measured reflections	l = −27→27
3539 independent reflections	3 standard reflections every 150 reflections
3121 reflections with I > 2σ(I)	intensity decay: 1.0%

Refinement

Refinement on F^2	w = 1/[σ^2(Fo^2) + (0.0496P)^2 + 2.4391P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.035	(Δ/σ)max = 0.001
wR(F^2) = 0.101	Δρmax = 0.24 e Å^−3
S = 1.02	Δρmin = −0.21 e Å^−3
3539 reflections	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
301 parameters	Extinction coefficient: 0.00076 (7)
All H-atom parameters refined

Special details

Refinement. Refinement was based on F² against all reflections. The weighted R-factor (wR) and goodness of fit (S) were based on F², and conventional R-factor (R) was calculated on F, with F set to zero for negative F². The threshold expression of I > 2σ(I) was used only for calculating R-factor(gt).

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

	x	y	z	Uiso*/Ueq
S1	0.60767 (2)	0.13736 (4)	1.02435 (2)	0.0419 (1)
O2	0.73603 (7)	0.6511 (1)	1.06995 (7)	0.0634 (4)
N3	0.55822 (6)	0.2130 (1)	0.90132 (5)	0.0364 (3)
C4	0.58841 (7)	0.2536 (2)	0.96234 (6)	0.0333 (3)
C5	0.60060 (8)	0.4141 (2)	0.97384 (6)	0.0339 (3)
C6	0.66277 (9)	0.4648 (2)	1.01515 (7)	0.0395 (3)
C7	0.67166 (9)	0.6138 (2)	1.02927 (8)	0.0453 (4)
C8	0.6176 (1)	0.7118 (2)	1.00276 (9)	0.0511 (4)
C9	0.5553 (1)	0.6599 (2)	0.96182 (9)	0.0489 (4)
C10	0.54620 (9)	0.5133 (2)	0.94661 (8)	0.0411 (3)
C11	0.7447 (2)	0.8002 (3)	1.0918 (1)	0.0791 (7)
C12	0.5243 (1)	0.0669 (2)	0.88499 (8)	0.0467 (4)
C13	0.5703 (1)	−0.0330 (2)	0.8576 (1)	0.0636 (5)
C14	0.4500 (1)	0.0867 (3)	0.8407 (1)	0.0663 (5)
C15	0.56519 (8)	0.3027 (2)	0.84872 (7)	0.0356 (3)
C16	0.62758 (8)	0.3304 (2)	0.83717 (7)	0.0361 (3)
C17	0.6964 (1)	0.2677 (2)	0.8760 (1)	0.0540 (4)
C18	0.63074 (8)	0.4328 (2)	0.78435 (7)	0.0383 (3)
C19	0.6728 (1)	0.4032 (2)	0.7431 (1)	0.0623 (5)
C20	0.6744 (2)	0.4993 (3)	0.6937 (1)	0.0765 (7)
C21	0.6348 (1)	0.6254 (3)	0.6851 (1)	0.0727 (6)
C22	0.5944 (1)	0.6574 (3)	0.7264 (1)	0.0699 (6)
C23	0.59225 (9)	0.5617 (2)	0.77584 (9)	0.0504 (4)
H6	0.6971 (9)	0.401 (2)	1.0332 (8)	0.04544 (6)*
H8	0.6235 (10)	0.811 (2)	1.0117 (9)	0.05285 (6)*
H9	0.516 (1)	0.729 (2)	0.9450 (9)	0.05611 (6)*
H10	0.5022 (9)	0.481 (2)	0.9203 (8)	0.03893 (5)*
H11A	0.793 (2)	0.798 (3)	1.121 (1)	0.0979 (1)*
H11B	0.741 (1)	0.870 (3)	1.055 (1)	0.0989 (1)*
H11C	0.710 (1)	0.826 (3)	1.115 (1)	0.07923 (9)*
H12	0.522 (1)	0.030 (2)	0.9252 (9)	0.05467 (6)*
H13A	0.546 (1)	−0.130 (3)	0.846 (1)	0.08349 (9)*
H13B	0.577 (1)	0.004 (3)	0.818 (1)	0.07873 (9)*
H13C	0.618 (1)	−0.045 (2)	0.888 (1)	0.07451 (8)*
H14A	0.424 (1)	0.158 (2)	0.859 (1)	0.06785 (8)*
H14B	0.451 (1)	0.122 (3)	0.797 (1)	0.08503 (9)*
H14C	0.424 (1)	−0.004 (3)	0.837 (1)	0.08456 (9)*
H15	0.5232 (9)	0.338 (2)	0.8214 (8)	0.04014 (5)*
H17A	0.691 (1)	0.198 (3)	0.905 (1)	0.06879 (8)*
H17B	0.723 (1)	0.222 (3)	0.850 (1)	0.08794 (9)*
H17C	0.731 (2)	0.343 (4)	0.899 (2)	0.1281 (1)*
H19	0.700 (1)	0.313 (3)	0.749 (1)	0.07761 (9)*
H20	0.703 (1)	0.476 (3)	0.668 (1)	0.09031 (10)*
H21	0.637 (1)	0.693 (3)	0.651 (1)	0.08788 (9)*
H22	0.567 (1)	0.747 (3)	0.723 (1)	0.08391 (9)*
H23	0.565 (1)	0.585 (2)	0.805 (1)	0.06052 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0599 (3)	0.0284 (2)	0.0349 (2)	0.0054 (2)	0.0080 (2)	0.0069 (1)
O2	0.0727 (9)	0.0455 (7)	0.0670 (8)	−0.0166 (6)	0.0096 (7)	−0.0137 (6)
N3	0.0441 (7)	0.0325 (6)	0.0323 (6)	−0.0038 (5)	0.0097 (5)	0.0042 (5)
C4	0.0358 (7)	0.0304 (7)	0.0347 (7)	0.0044 (6)	0.0112 (5)	0.0040 (5)
C5	0.0428 (8)	0.0278 (6)	0.0340 (7)	0.0049 (6)	0.0148 (6)	0.0046 (5)
C6	0.0471 (8)	0.0304 (7)	0.0398 (7)	0.0052 (6)	0.0096 (6)	0.0033 (6)
C7	0.0597 (10)	0.0350 (8)	0.0445 (8)	−0.0068 (7)	0.0194 (7)	−0.0028 (6)
C8	0.079 (1)	0.0250 (7)	0.060 (1)	0.0044 (8)	0.0369 (9)	0.0026 (7)
C9	0.060 (1)	0.0340 (8)	0.0605 (10)	0.0164 (8)	0.0298 (8)	0.0126 (7)
C10	0.0439 (8)	0.0375 (8)	0.0447 (8)	0.0087 (7)	0.0166 (7)	0.0090 (6)
C11	0.100 (2)	0.055 (1)	0.087 (2)	−0.031 (1)	0.033 (2)	−0.029 (1)
C12	0.064 (1)	0.0382 (8)	0.0375 (8)	−0.0144 (7)	0.0123 (7)	0.0014 (6)
C13	0.092 (2)	0.0370 (9)	0.063 (1)	−0.0019 (10)	0.023 (1)	−0.0020 (9)
C14	0.063 (1)	0.065 (1)	0.066 (1)	−0.022 (1)	0.0076 (10)	−0.007 (1)
C15	0.0404 (8)	0.0342 (7)	0.0308 (7)	−0.0002 (6)	0.0069 (6)	0.0055 (6)
C16	0.0430 (8)	0.0337 (7)	0.0328 (7)	0.0027 (6)	0.0120 (6)	0.0016 (6)
C17	0.0454 (9)	0.062 (1)	0.057 (1)	0.0156 (9)	0.0184 (8)	0.0191 (9)
C18	0.0417 (8)	0.0395 (7)	0.0333 (7)	−0.0072 (6)	0.0092 (6)	0.0023 (6)
C19	0.086 (1)	0.053 (1)	0.061 (1)	−0.002 (1)	0.042 (1)	0.0014 (9)
C20	0.105 (2)	0.081 (2)	0.059 (1)	−0.018 (1)	0.050 (1)	0.003 (1)
C21	0.078 (1)	0.086 (2)	0.052 (1)	−0.021 (1)	0.0132 (10)	0.030 (1)
C22	0.058 (1)	0.071 (1)	0.079 (1)	0.004 (1)	0.015 (1)	0.041 (1)
C23	0.0443 (9)	0.0551 (10)	0.0529 (9)	0.0048 (8)	0.0149 (7)	0.0195 (8)

Geometric parameters (Å, º)

S1—C4	1.671 (1)	C13—H13B	0.95 (3)
O2—C7	1.370 (2)	C13—H13C	1.00 (2)
O2—C11	1.434 (3)	C14—H14A	0.97 (2)
N3—C4	1.345 (2)	C14—H14B	1.00 (3)
N3—C12	1.487 (2)	C14—H14C	0.96 (3)
N3—C15	1.435 (2)	C15—C16	1.329 (2)
C4—C5	1.492 (2)	C15—H15	0.93 (2)
C5—C6	1.380 (2)	C16—C17	1.495 (2)
C5—C10	1.398 (2)	C16—C18	1.488 (2)
C6—C7	1.392 (2)	C17—H17A	0.92 (2)
C6—H6	0.89 (2)	C17—H17B	0.95 (3)
C7—C8	1.384 (2)	C17—H17C	1.00 (3)
C8—C9	1.382 (3)	C18—C19	1.387 (3)
C8—H8	0.93 (2)	C18—C23	1.379 (2)
C9—C10	1.376 (2)	C19—C20	1.388 (3)
C9—H9	0.98 (2)	C19—H19	0.97 (2)
C10—H10	0.94 (2)	C20—C21	1.368 (4)
C11—H11A	0.97 (3)	C20—H20	0.91 (3)
C11—H11B	1.01 (3)	C21—C22	1.369 (4)
C11—H11C	0.97 (3)	C21—H21	0.98 (3)
C12—C13	1.505 (3)	C22—C23	1.389 (3)
C12—C14	1.521 (3)	C22—H22	0.96 (2)
C12—H12	0.94 (2)	C23—H23	0.95 (2)
C13—H13A	1.00 (2)
C7—O2—C11	117.0 (2)	H13A—C13—H13B	104 (2)
C4—N3—C12	122.0 (1)	H13A—C13—H13C	111 (1)
C4—N3—C15	120.7 (1)	H13B—C13—H13C	108 (2)
C12—N3—C15	116.8 (1)	C12—C14—H14A	109 (1)
S1—C4—N3	123.9 (1)	C12—C14—H14B	111 (1)
S1—C4—C5	119.7 (1)	C12—C14—H14C	110 (1)
N3—C4—C5	116.2 (1)	H14A—C14—H14B	108 (1)
C4—C5—C6	120.6 (1)	H14A—C14—H14C	107 (2)
C4—C5—C10	119.6 (1)	H14B—C14—H14C	109 (2)
C6—C5—C10	119.5 (1)	N3—C15—C16	122.7 (1)
C5—C6—C7	120.3 (1)	N3—C15—H15	116 (1)
C5—C6—H6	119 (1)	C16—C15—H15	120 (1)
C7—C6—H6	120 (1)	C15—C16—C17	123.4 (2)
O2—C7—C6	115.0 (1)	C15—C16—C18	119.3 (1)
O2—C7—C8	124.9 (1)	C17—C16—C18	117.2 (2)
C6—C7—C8	120.1 (1)	C16—C17—H17A	113 (1)
C7—C8—C9	119.1 (1)	C16—C17—H17B	112 (1)
C7—C8—H8	120 (1)	C16—C17—H17C	114 (1)
C9—C8—H8	120 (1)	H17A—C17—H17B	106 (2)
C8—C9—C10	121.4 (2)	H17A—C17—H17C	108 (2)
C8—C9—H9	118 (1)	H17B—C17—H17C	100 (2)
C10—C9—H9	119 (1)	C16—C18—C19	121.5 (1)
C5—C10—C9	119.4 (1)	C16—C18—C23	120.3 (2)
C5—C10—H10	121 (1)	C19—C18—C23	118.2 (2)
C9—C10—H10	119 (1)	C18—C19—C20	120.7 (2)
O2—C11—H11A	101 (1)	C18—C19—H19	118 (1)
O2—C11—H11B	110 (1)	C20—C19—H19	120 (1)
O2—C11—H11C	111 (1)	C19—C20—C21	120.5 (3)
H11A—C11—H11B	111 (2)	C19—C20—H20	117 (1)
H11A—C11—H11C	110 (2)	C21—C20—H20	121 (1)
H11B—C11—H11C	111 (2)	C20—C21—C22	119.4 (2)
N3—C12—C13	111.2 (2)	C20—C21—H21	120 (1)
N3—C12—C14	109.4 (1)	C22—C21—H21	120 (1)
N3—C12—H12	103 (1)	C21—C22—C23	120.5 (2)
C13—C12—C14	113.0 (2)	C21—C22—H22	121 (1)
C13—C12—H12	109 (1)	C23—C22—H22	117 (1)
C14—C12—H12	110 (1)	C18—C23—C22	120.7 (2)
C12—C13—H13A	109 (1)	C18—C23—H23	118 (1)
C12—C13—H13B	111 (1)	C22—C23—H23	120 (1)
C12—C13—H13C	110 (1)