1-(4-Ethoxy-benzo-yl)-4-(4-methoxy-phen-yl)thiosemicarbazide.

The title compound, C(17)H(19)N(3)O(3)S, crystallizes with two closely similar independent mol-ecules related by a pseudotranslation of c/2. Each mol-ecule consists of three approximately planar moieties centred on the N(2)CS group and the two ring systems. The packing involves classical H bonds of the form N(amide)-H⋯S and N(hydrazine)-H⋯OC, together with various weak hydrogen bonds and N(hydrazine)-H⋯π inter-actions. The overall packing is three-dimensional, but layer substructures parallel to the xz plane can be readily identified. Each mol-ecule forms a topologically equivalent set of hydrogen-bond inter-actions.

Related literature

Thio­semicarbazides represent a class of versatile precursors for the syntheses of various nitro­gen heterocycles, see: Al-Masoudi et al. (2006 ▶); Kucukguzel et al. (2007 ▶); Serwar et al.2009 ▶); Serwer et al. (2008 ▶); Tomascikava et al. (2008 ▶); Tozkoparan et al. (2007 ▶). For the pharmaceutical potential of the thio­semicarbazide moiety, see: Angelusiu et al. (2009 ▶); Ghosh et al. (2009 ▶); Liu et al. (2009 ▶).

Experimental

Crystal data

C17H19N3O3S

M = 345.41

Monoclinic,

a = 15.40429 (13) Å

b = 9.67120 (9) Å

c = 11.69922 (9) Å

β = 95.0922 (7)°

V = 1736.05 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 100 K

0.3 × 0.2 × 0.1 mm

Data collection

Oxford Diffraction Xcalibur E diffractometer

Absorption correction: multi-scan (CrysAlisPro; Oxford Diffraction, 2009 ▶) T min = 0.981, T max = 1.000

44704 measured reflections

9918 independent reflections

6348 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.055

S = 0.96

9918 reflections

461 parameters

16 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983 ▶), 4562 Friedel pairs

Flack parameter: 0.01 (3)

Data collection: CrysAlisPro (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlisPro; data reduction: CrysAlisPro; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Siemens, 1994 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809036599/bt5057sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036599/bt5057Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H19N3O3S	F(000) = 728
Mr = 345.41	Dx = 1.322 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 15.40429 (13) Å	Cell parameters from 16506 reflections
b = 9.67120 (9) Å	θ = 2.3–30.7°
c = 11.69922 (9) Å	µ = 0.21 mm−1
β = 95.0922 (7)°	T = 100 K
V = 1736.05 (3) Å3	Tablet, colourless
Z = 4	0.3 × 0.2 × 0.1 mm

Oxford Diffraction Xcalibur E diffractometer	9918 independent reflections
Radiation source: Enhance (Mo) X-ray Source	6348 reflections with I > 2σ(I)
graphite	Rint = 0.032
Detector resolution: 16.1419 pixels mm-1	θmax = 30.5°, θmin = 2.3°
ω–scan	h = −21→21
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −13→13
Tmin = 0.981, Tmax = 1.000	l = −15→16
44704 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.055	w = 1/[σ2(Fo2) + (0.020P)2] where P = (Fo2 + 2Fc2)/3
S = 0.96	(Δ/σ)max = 0.001
9918 reflections	Δρmax = 0.30 e Å−3
461 parameters	Δρmin = −0.23 e Å−3
16 restraints	Absolute structure: Flack (1983), 4562 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (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)13.0283 (0.0011) x + 1.4133 (0.0037) y - 6.8581 (0.0016) z = 2.4289 (0.0026)* 0.0169 (0.0013) C6 * 0.0162 (0.0012) C7 * 0.0312 (0.0012) C8 * 0.0483 (0.0013) C9 * 0.0676 (0.0014) C10 * 0.0481 (0.0013) C11 * 0.0436 (0.0010) O2 * -0.0206 (0.0014) C12 * -0.1392 (0.0013) C13 * 0.0011 (0.0013) C5 * -0.0780 (0.0010) O1 * 0.0952 (0.0010) N4 * -0.1306 (0.0010) N3Rms deviation of fitted atoms = 0.0705- 5.8835 (0.0067) x + 8.3025 (0.0025) y + 4.3848 (0.0043) z = 4.5767 (0.0054)Angle to previous plane (with approximate e.s.d.) = 68.09 (0.03)* -0.0909 (0.0013) N1 * -0.0296 (0.0012) C2 * 0.0247 (0.0006) S * 0.0499 (0.0008) N4 * -0.0143 (0.0011) N3 * 0.0602 (0.0008) C14Rms deviation of fitted atoms = 0.05184.4124 (0.0064) x - 7.2670 (0.0036) y + 6.6294 (0.0075) z = 4.1549 (0.0063)Angle to previous plane (with approximate e.s.d.) = 56.56 (0.04)* 0.0131 (0.0015) C14 * 0.0077 (0.0017) C15 * -0.0154 (0.0018) C16 * 0.0007 (0.0017) C17 * -0.0065 (0.0015) C18 * -0.0105 (0.0015) C19 * -0.0002 (0.0013) O3 * 0.0099 (0.0013) C20 * 0.0012 (0.0012) N1Rms deviation of fitted atoms = 0.008913.0659 (0.0012) x + 1.8489 (0.0037) y - 6.6371 (0.0017) z = 6.1077 (0.0017)Angle to previous plane (with approximate e.s.d.) = 78.79 (0.03)* 0.0172 (0.0013) C6' * 0.0319 (0.0011) C7' * 0.0585 (0.0011) C8' * 0.0569 (0.0013) C9' * 0.0548 (0.0014) C10' * 0.0249 (0.0013) C11' * 0.0496 (0.0010) O2' * -0.0083 (0.0015) C12' * -0.1597 (0.0014) C13' * -0.0114 (0.0013) C5' * -0.1233 (0.0010) O1' * 0.1239 (0.0010) N4' * -0.1150 (0.0010) N3'Rms deviation of fitted atoms = 0.0802- 4.7715 (0.0070) x + 8.8203 (0.0020) y + 3.4544 (0.0044) z = 2.9970 (0.0051)Angle to previous plane (with approximate e.s.d.) = 77.22 (0.03)* -0.0881 (0.0013) N1' * -0.0271 (0.0012) C2' * 0.0344 (0.0006) S' * 0.0675 (0.0008) N4' * -0.0418 (0.0011) N3' * 0.0550 (0.0008) C14'Rms deviation of fitted atoms = 0.05632.1176 (0.0060) x - 6.0315 (0.0044) y + 8.8245 (0.0052) z = 0.7518 (0.0041)Angle to previous plane (with approximate e.s.d.) = 66.14 (0.03)* 0.0140 (0.0014) C14' * 0.0048 (0.0014) C15' * -0.0082 (0.0014) C16' * -0.0043 (0.0016) C17' * -0.0002 (0.0015) C18' * -0.0089 (0.0014) C19' * -0.0003 (0.0013) O3' * 0.0060 (0.0013) C20' * -0.0029 (0.0012) N1'Rms deviation of fitted atoms = 0.0069

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.

	x	y	z	Uiso*/Ueq
S	0.70206 (2)	0.50456 (5)	1.03604 (3)	0.01728 (10)
O1	0.52373 (7)	0.30901 (11)	0.71581 (8)	0.0180 (2)
O2	0.28479 (6)	0.55263 (11)	0.29437 (8)	0.0211 (3)
O3	1.02907 (7)	0.86352 (16)	0.88836 (10)	0.0411 (4)
N1	0.70429 (8)	0.60538 (15)	0.82176 (11)	0.0181 (3)
H01	0.6823 (9)	0.6052 (17)	0.7547 (10)	0.021 (5)*
C2	0.66134 (9)	0.54043 (16)	0.90110 (11)	0.0125 (3)
N3	0.57906 (8)	0.50134 (15)	0.86822 (10)	0.0142 (3)
H03	0.5512 (8)	0.4637 (14)	0.9164 (10)	0.005 (4)*
N4	0.53669 (8)	0.53524 (14)	0.76180 (10)	0.0133 (3)
H04	0.5143 (10)	0.6113 (14)	0.7606 (14)	0.027 (6)*
C5	0.50445 (9)	0.42990 (16)	0.69256 (13)	0.0128 (3)
C6	0.44704 (9)	0.47015 (16)	0.58951 (12)	0.0122 (3)
C7	0.41778 (9)	0.36550 (16)	0.51243 (12)	0.0148 (4)
H7	0.4349	0.2724	0.5274	0.018*
C8	0.36421 (10)	0.39690 (17)	0.41495 (12)	0.0169 (4)
H8	0.3447	0.3252	0.3634	0.020*
C9	0.33859 (9)	0.53260 (17)	0.39175 (12)	0.0157 (3)
C10	0.36805 (10)	0.63793 (17)	0.46663 (12)	0.0171 (4)
H10	0.3516	0.7311	0.4507	0.021*
C11	0.42156 (10)	0.60574 (16)	0.56447 (13)	0.0157 (4)
H11	0.4413	0.6777	0.6156	0.019*
C12	0.25273 (10)	0.69102 (17)	0.27136 (13)	0.0244 (4)
H12A	0.3015	0.7539	0.2577	0.029*
H12B	0.2234	0.7264	0.3374	0.029*
C13	0.18893 (11)	0.68298 (19)	0.16578 (13)	0.0312 (5)
H13A	0.2177	0.6421	0.1025	0.047*
H13B	0.1685	0.7762	0.1443	0.047*
H13C	0.1391	0.6255	0.1821	0.047*
C14	0.78727 (10)	0.67202 (18)	0.84138 (13)	0.0198 (4)
C15	0.85155 (11)	0.6460 (2)	0.76923 (14)	0.0428 (6)
H15	0.8414	0.5821	0.7078	0.051*
C16	0.93107 (12)	0.7134 (3)	0.78670 (14)	0.0503 (7)
H16	0.9746	0.6970	0.7357	0.060*
C17	0.94779 (10)	0.8035 (2)	0.87684 (14)	0.0298 (5)
C18	0.88347 (10)	0.83019 (18)	0.94777 (15)	0.0270 (4)
H18	0.8938	0.8933	1.0097	0.032*
C19	0.80302 (10)	0.76466 (18)	0.92888 (15)	0.0272 (4)
H19	0.7584	0.7846	0.9775	0.033*
C20	1.04658 (11)	0.9572 (2)	0.98097 (15)	0.0376 (5)
H20A	1.0051	1.0342	0.9729	0.056*
H20B	1.1061	0.9930	0.9803	0.056*
H20C	1.0406	0.9092	1.0536	0.056*
S'	0.69682 (2)	0.51034 (4)	0.53698 (3)	0.01624 (9)
O1'	0.52337 (7)	0.30780 (11)	0.21440 (8)	0.0184 (2)
O2'	0.28670 (6)	0.54492 (11)	−0.21151 (8)	0.0215 (3)
O3'	1.04034 (7)	0.80274 (17)	0.38417 (11)	0.0439 (4)
N1'	0.70424 (8)	0.58667 (14)	0.31685 (11)	0.0161 (3)
H01'	0.6834 (9)	0.5828 (16)	0.2504 (10)	0.017 (5)*
C2'	0.65809 (9)	0.53631 (15)	0.39935 (11)	0.0122 (3)
N3'	0.57447 (7)	0.50178 (15)	0.36778 (10)	0.0139 (3)
H03'	0.5419 (8)	0.4738 (15)	0.4176 (10)	0.012 (4)*
N4'	0.53359 (8)	0.53414 (14)	0.26033 (10)	0.0133 (3)
H04'	0.5104 (10)	0.6123 (14)	0.2551 (13)	0.023 (5)*
C5'	0.50319 (9)	0.42750 (16)	0.19115 (12)	0.0130 (3)
C6'	0.44667 (9)	0.46655 (16)	0.08647 (12)	0.0118 (3)
C7'	0.42218 (9)	0.36192 (16)	0.00689 (12)	0.0140 (3)
H7'	0.4418	0.2699	0.0212	0.017*
C8'	0.36966 (9)	0.39163 (17)	−0.09224 (12)	0.0152 (3)
H8'	0.3539	0.3203	−0.1460	0.018*
C9'	0.33984 (9)	0.52599 (17)	−0.11327 (12)	0.0157 (3)
C10'	0.36423 (10)	0.63083 (17)	−0.03574 (13)	0.0173 (4)
H10'	0.3450	0.7229	−0.0508	0.021*
C11'	0.41673 (10)	0.60055 (16)	0.06368 (13)	0.0155 (4)
H11'	0.4325	0.6723	0.1170	0.019*
C12'	0.25161 (11)	0.68144 (18)	−0.23382 (14)	0.0274 (4)
H12C	0.2990	0.7471	−0.2472	0.033*
H12D	0.2217	0.7144	−0.1675	0.033*
C13'	0.18795 (12)	0.6718 (2)	−0.33901 (14)	0.0392 (5)
H13D	0.2167	0.6298	−0.4019	0.059*
H13E	0.1676	0.7647	−0.3616	0.059*
H13F	0.1381	0.6147	−0.3220	0.059*
C14'	0.79061 (10)	0.64214 (18)	0.33595 (13)	0.0187 (4)
C15'	0.85761 (10)	0.5858 (2)	0.28031 (13)	0.0280 (4)
H15'	0.8472	0.5088	0.2305	0.034*
C16'	0.94058 (10)	0.6430 (2)	0.29804 (13)	0.0350 (5)
H16'	0.9869	0.6051	0.2597	0.042*
C17'	0.95622 (10)	0.7544 (2)	0.37088 (14)	0.0294 (5)
C18'	0.88890 (10)	0.81103 (19)	0.42619 (15)	0.0282 (4)
H18'	0.8994	0.8873	0.4767	0.034*
C19'	0.80553 (10)	0.75494 (18)	0.40688 (14)	0.0259 (4)
H19'	0.7586	0.7948	0.4429	0.031*
C20'	1.05700 (12)	0.9175 (2)	0.45930 (16)	0.0441 (6)
H20D	1.0241	0.9980	0.4285	0.066*
H20E	1.1194	0.9387	0.4658	0.066*
H20F	1.0389	0.8946	0.5352	0.066*

	U11	U22	U33	U12	U13	U23
S	0.0191 (2)	0.0208 (3)	0.01124 (19)	−0.0005 (2)	−0.00234 (16)	0.00053 (18)
O1	0.0241 (6)	0.0118 (6)	0.0177 (6)	0.0013 (5)	−0.0002 (5)	0.0031 (5)
O2	0.0243 (6)	0.0218 (7)	0.0157 (6)	0.0006 (5)	−0.0066 (5)	0.0002 (5)
O3	0.0235 (7)	0.0669 (11)	0.0330 (7)	−0.0240 (7)	0.0037 (6)	−0.0058 (7)
N1	0.0150 (7)	0.0272 (9)	0.0117 (7)	−0.0055 (6)	−0.0012 (6)	0.0051 (6)
C2	0.0115 (7)	0.0120 (9)	0.0140 (8)	0.0012 (6)	0.0010 (6)	−0.0018 (6)
N3	0.0154 (6)	0.0180 (8)	0.0092 (7)	−0.0034 (6)	0.0009 (5)	0.0031 (6)
N4	0.0148 (7)	0.0116 (8)	0.0127 (7)	0.0000 (6)	−0.0026 (5)	0.0001 (6)
C5	0.0123 (8)	0.0125 (9)	0.0143 (8)	−0.0011 (7)	0.0043 (6)	0.0009 (7)
C6	0.0129 (8)	0.0110 (9)	0.0131 (8)	−0.0026 (6)	0.0023 (6)	−0.0001 (6)
C7	0.0164 (8)	0.0111 (9)	0.0172 (9)	−0.0009 (7)	0.0039 (7)	0.0010 (7)
C8	0.0177 (8)	0.0182 (10)	0.0144 (8)	−0.0043 (7)	−0.0002 (7)	−0.0049 (7)
C9	0.0121 (7)	0.0210 (10)	0.0138 (8)	−0.0019 (7)	0.0004 (6)	0.0034 (7)
C10	0.0221 (8)	0.0117 (9)	0.0170 (9)	0.0005 (7)	−0.0009 (7)	−0.0008 (7)
C11	0.0174 (8)	0.0131 (10)	0.0161 (9)	−0.0017 (7)	−0.0016 (7)	−0.0051 (7)
C12	0.0244 (10)	0.0245 (11)	0.0233 (10)	0.0044 (8)	−0.0041 (8)	0.0023 (8)
C13	0.0273 (10)	0.0399 (12)	0.0246 (10)	0.0040 (8)	−0.0076 (8)	0.0047 (8)
C14	0.0119 (8)	0.0278 (10)	0.0194 (9)	−0.0038 (7)	−0.0005 (6)	0.0082 (7)
C15	0.0288 (10)	0.0805 (18)	0.0202 (9)	−0.0255 (11)	0.0082 (7)	−0.0192 (10)
C16	0.0298 (11)	0.096 (2)	0.0274 (10)	−0.0292 (11)	0.0170 (8)	−0.0178 (11)
C17	0.0194 (9)	0.0454 (13)	0.0240 (9)	−0.0128 (8)	−0.0023 (7)	0.0086 (8)
C18	0.0211 (9)	0.0215 (10)	0.0387 (10)	−0.0053 (7)	0.0048 (8)	−0.0080 (8)
C19	0.0180 (9)	0.0214 (10)	0.0434 (10)	−0.0038 (7)	0.0087 (8)	−0.0077 (8)
C20	0.0245 (9)	0.0496 (13)	0.0374 (10)	−0.0197 (9)	−0.0049 (8)	0.0030 (9)
S'	0.0178 (2)	0.0181 (2)	0.01218 (19)	0.0001 (2)	−0.00225 (15)	−0.00011 (18)
O1'	0.0255 (6)	0.0116 (7)	0.0178 (6)	0.0013 (5)	−0.0007 (5)	0.0025 (5)
O2'	0.0246 (6)	0.0232 (7)	0.0151 (6)	−0.0011 (5)	−0.0079 (5)	−0.0006 (5)
O3'	0.0182 (6)	0.0690 (11)	0.0448 (8)	−0.0180 (7)	0.0041 (6)	−0.0062 (7)
N1'	0.0131 (7)	0.0236 (8)	0.0113 (7)	−0.0032 (6)	−0.0004 (6)	0.0006 (6)
C2'	0.0149 (8)	0.0081 (9)	0.0139 (8)	0.0017 (6)	0.0026 (6)	−0.0011 (6)
N3'	0.0121 (6)	0.0188 (8)	0.0105 (7)	−0.0020 (6)	−0.0004 (5)	0.0015 (6)
N4'	0.0139 (7)	0.0130 (9)	0.0124 (7)	0.0014 (6)	−0.0019 (5)	0.0020 (6)
C5'	0.0128 (8)	0.0138 (9)	0.0131 (8)	−0.0018 (7)	0.0042 (6)	0.0003 (7)
C6'	0.0096 (7)	0.0125 (9)	0.0134 (8)	−0.0018 (6)	0.0019 (6)	0.0016 (7)
C7'	0.0154 (8)	0.0114 (9)	0.0156 (8)	−0.0026 (7)	0.0037 (7)	−0.0018 (7)
C8'	0.0155 (8)	0.0156 (9)	0.0148 (8)	−0.0047 (7)	0.0031 (6)	−0.0026 (7)
C9'	0.0130 (7)	0.0238 (10)	0.0103 (7)	−0.0012 (7)	0.0006 (6)	0.0009 (7)
C10'	0.0180 (8)	0.0158 (9)	0.0178 (9)	0.0039 (7)	−0.0008 (7)	0.0037 (7)
C11'	0.0185 (8)	0.0131 (9)	0.0149 (9)	−0.0012 (7)	0.0008 (7)	−0.0017 (7)
C12'	0.0286 (10)	0.0264 (11)	0.0255 (10)	0.0024 (8)	−0.0079 (8)	0.0030 (8)
C13'	0.0399 (12)	0.0448 (14)	0.0299 (11)	0.0070 (10)	−0.0142 (9)	0.0026 (9)
C14'	0.0142 (8)	0.0253 (10)	0.0165 (8)	−0.0027 (7)	0.0009 (6)	0.0047 (7)
C15'	0.0187 (8)	0.0423 (12)	0.0233 (9)	−0.0025 (8)	0.0040 (7)	−0.0088 (8)
C16'	0.0164 (9)	0.0614 (14)	0.0277 (10)	−0.0018 (9)	0.0056 (7)	−0.0101 (9)
C17'	0.0150 (8)	0.0459 (13)	0.0266 (9)	−0.0101 (8)	−0.0013 (7)	0.0057 (9)
C18'	0.0212 (9)	0.0248 (10)	0.0384 (10)	−0.0065 (8)	0.0009 (8)	−0.0009 (8)
C19'	0.0145 (8)	0.0262 (11)	0.0377 (10)	−0.0007 (7)	0.0060 (7)	−0.0030 (8)
C20'	0.0260 (10)	0.0522 (14)	0.0521 (13)	−0.0214 (10)	−0.0083 (9)	0.0102 (10)

S—C2	1.6823 (14)	C14'—C19'	1.378 (2)
O1—C5	1.2307 (17)	C14'—C15'	1.380 (2)
O2—C9	1.3618 (16)	C15'—C16'	1.391 (2)
O2—C12	1.4436 (18)	C16'—C17'	1.382 (2)
O3—C17	1.3757 (18)	C17'—C18'	1.383 (2)
O3—C20	1.420 (2)	C18'—C19'	1.394 (2)
N1—C2	1.3428 (18)	N1—H01	0.826 (11)
N1—C14	1.4316 (19)	N3—H03	0.822 (10)
C2—N3	1.3457 (17)	N4—H04	0.812 (12)
N3—N4	1.3926 (16)	C7—H7	0.9500
N4—C5	1.3672 (19)	C8—H8	0.9500
C5—C6	1.482 (2)	C10—H10	0.9500
C6—C11	1.393 (2)	C11—H11	0.9500
C6—C7	1.4030 (19)	C12—H12A	0.9900
C7—C8	1.3809 (19)	C12—H12B	0.9900
C8—C9	1.390 (2)	C13—H13A	0.9800
C9—C10	1.393 (2)	C13—H13B	0.9800
C10—C11	1.3853 (19)	C13—H13C	0.9800
C12—C13	1.5108 (19)	C15—H15	0.9500
C14—C19	1.366 (2)	C16—H16	0.9500
C14—C15	1.380 (2)	C18—H18	0.9500
C15—C16	1.387 (2)	C19—H19	0.9500
C16—C17	1.375 (3)	C20—H20A	0.9800
C17—C18	1.372 (2)	C20—H20B	0.9800
C18—C19	1.392 (2)	C20—H20C	0.9800
S'—C2'	1.6856 (14)	N1'—H01'	0.816 (11)
O1'—C5'	1.2229 (17)	N3'—H03'	0.847 (10)
O2'—C9'	1.3630 (16)	N4'—H04'	0.836 (12)
O2'—C12'	1.4417 (19)	C7'—H7'	0.9500
O3'—C17'	1.3733 (18)	C8'—H8'	0.9500
O3'—C20'	1.425 (2)	C10'—H10'	0.9500
N1'—C2'	1.3402 (17)	C11'—H11'	0.9500
N1'—C14'	1.4335 (19)	C12'—H12C	0.9900
C2'—N3'	1.3501 (17)	C12'—H12D	0.9900
N3'—N4'	1.3908 (16)	C13'—H13D	0.9800
N4'—C5'	1.3678 (19)	C13'—H13E	0.9800
C5'—C6'	1.487 (2)	C13'—H13F	0.9800
C6'—C11'	1.393 (2)	C15'—H15'	0.9500
C6'—C7'	1.4039 (19)	C16'—H16'	0.9500
C7'—C8'	1.3840 (19)	C18'—H18'	0.9500
C8'—C9'	1.393 (2)	C19'—H19'	0.9500
C9'—C10'	1.390 (2)	C20'—H20D	0.9800
C10'—C11'	1.3877 (19)	C20'—H20E	0.9800
C12'—C13'	1.507 (2)	C20'—H20F	0.9800
C9—O2—C12	117.42 (12)	C6—C7—H7	119.8
C17—O3—C20	116.97 (14)	C7—C8—H8	119.8
C2—N1—C14	125.98 (13)	C9—C8—H8	119.8
N1—C2—N3	116.31 (13)	C11—C10—H10	120.3
N1—C2—S	125.42 (11)	C9—C10—H10	120.3
N3—C2—S	118.27 (11)	C10—C11—H11	119.3
C2—N3—N4	122.97 (12)	C6—C11—H11	119.3
C5—N4—N3	118.10 (13)	O2—C12—H12A	110.3
O1—C5—N4	120.60 (15)	C13—C12—H12A	110.3
O1—C5—C6	122.96 (14)	O2—C12—H12B	110.3
N4—C5—C6	116.44 (14)	C13—C12—H12B	110.3
C11—C6—C7	118.40 (14)	H12A—C12—H12B	108.6
C11—C6—C5	123.71 (13)	C12—C13—H13A	109.5
C7—C6—C5	117.89 (14)	C12—C13—H13B	109.5
C8—C7—C6	120.43 (15)	H13A—C13—H13B	109.5
C7—C8—C9	120.49 (15)	C12—C13—H13C	109.5
O2—C9—C8	116.02 (14)	H13A—C13—H13C	109.5
O2—C9—C10	124.21 (15)	H13B—C13—H13C	109.5
C8—C9—C10	119.77 (14)	C14—C15—H15	120.1
C11—C10—C9	119.48 (15)	C16—C15—H15	120.1
C10—C11—C6	121.42 (14)	C17—C16—H16	119.5
O2—C12—C13	106.96 (13)	C15—C16—H16	119.5
C19—C14—C15	119.26 (15)	C17—C18—H18	120.0
C19—C14—N1	120.81 (15)	C19—C18—H18	120.0
C15—C14—N1	119.90 (15)	C14—C19—H19	119.5
C14—C15—C16	119.76 (17)	C18—C19—H19	119.5
C17—C16—C15	120.94 (17)	O3—C20—H20A	109.5
C18—C17—C16	119.13 (16)	O3—C20—H20B	109.5
C18—C17—O3	124.15 (16)	H20A—C20—H20B	109.5
C16—C17—O3	116.71 (16)	O3—C20—H20C	109.5
C17—C18—C19	119.93 (16)	H20A—C20—H20C	109.5
C14—C19—C18	120.94 (16)	H20B—C20—H20C	109.5
C9'—O2'—C12'	117.59 (12)	C2'—N1'—H01'	118.7 (11)
C17'—O3'—C20'	116.84 (14)	C14'—N1'—H01'	116.6 (11)
C2'—N1'—C14'	124.62 (13)	C2'—N3'—H03'	120.0 (9)
N1'—C2'—N3'	116.56 (13)	N4'—N3'—H03'	116.5 (9)
N1'—C2'—S'	125.22 (11)	C5'—N4'—H04'	121.1 (11)
N3'—C2'—S'	118.21 (11)	N3'—N4'—H04'	115.2 (11)
C2'—N3'—N4'	122.41 (12)	C8'—C7'—H7'	119.7
C5'—N4'—N3'	117.96 (13)	C6'—C7'—H7'	119.7
O1'—C5'—N4'	121.01 (15)	C7'—C8'—H8'	120.0
O1'—C5'—C6'	122.84 (14)	C9'—C8'—H8'	120.0
N4'—C5'—C6'	116.14 (14)	C11'—C10'—H10'	120.1
C11'—C6'—C7'	118.59 (14)	C9'—C10'—H10'	120.1
C11'—C6'—C5'	123.61 (14)	C10'—C11'—H11'	119.5
C7'—C6'—C5'	117.80 (14)	C6'—C11'—H11'	119.5
C8'—C7'—C6'	120.58 (15)	O2'—C12'—H12C	110.3
C7'—C8'—C9'	120.05 (14)	C13'—C12'—H12C	110.3
O2'—C9'—C10'	124.03 (15)	O2'—C12'—H12D	110.3
O2'—C9'—C8'	115.99 (14)	C13'—C12'—H12D	110.3
C10'—C9'—C8'	119.97 (14)	H12C—C12'—H12D	108.5
C11'—C10'—C9'	119.79 (15)	C12'—C13'—H13D	109.5
C10'—C11'—C6'	121.00 (15)	C12'—C13'—H13E	109.5
O2'—C12'—C13'	107.32 (14)	H13D—C13'—H13E	109.5
C19'—C14'—C15'	120.33 (15)	C12'—C13'—H13F	109.5
C19'—C14'—N1'	119.55 (15)	H13D—C13'—H13F	109.5
C15'—C14'—N1'	120.08 (15)	H13E—C13'—H13F	109.5
C14'—C15'—C16'	119.21 (17)	C14'—C15'—H15'	120.4
C17'—C16'—C15'	120.65 (16)	C16'—C15'—H15'	120.4
O3'—C17'—C16'	116.52 (16)	C17'—C16'—H16'	119.7
O3'—C17'—C18'	123.46 (17)	C15'—C16'—H16'	119.7
C16'—C17'—C18'	120.02 (16)	C17'—C18'—H18'	120.4
C17'—C18'—C19'	119.23 (17)	C19'—C18'—H18'	120.4
C14'—C19'—C18'	120.52 (16)	C14'—C19'—H19'	119.7
C2—N1—H01	118.0 (11)	C18'—C19'—H19'	119.7
C14—N1—H01	116.0 (11)	O3'—C20'—H20D	109.5
C2—N3—H03	117.6 (9)	O3'—C20'—H20E	109.5
N4—N3—H03	119.0 (9)	H20D—C20'—H20E	109.5
C5—N4—H04	122.2 (12)	O3'—C20'—H20F	109.5
N3—N4—H04	113.2 (12)	H20D—C20'—H20F	109.5
C8—C7—H7	119.8	H20E—C20'—H20F	109.5
C14—N1—C2—N3	171.14 (15)	C14'—N1'—C2'—N3'	173.21 (15)
C14—N1—C2—S	−9.0 (2)	C14'—N1'—C2'—S'	−8.1 (2)
N1—C2—N3—N4	−5.3 (2)	N1'—C2'—N3'—N4'	−9.0 (2)
S—C2—N3—N4	174.82 (11)	S'—C2'—N3'—N4'	172.22 (11)
C2—N3—N4—C5	123.25 (16)	C2'—N3'—N4'—C5'	119.34 (16)
N3—N4—C5—O1	−10.8 (2)	N3'—N4'—C5'—O1'	−11.7 (2)
N3—N4—C5—C6	169.88 (12)	N3'—N4'—C5'—C6'	169.66 (11)
O1—C5—C6—C11	177.14 (15)	O1'—C5'—C6'—C11'	174.11 (15)
N4—C5—C6—C11	−3.6 (2)	N4'—C5'—C6'—C11'	−7.2 (2)
O1—C5—C6—C7	−3.6 (2)	O1'—C5'—C6'—C7'	−5.6 (2)
N4—C5—C6—C7	175.64 (13)	N4'—C5'—C6'—C7'	173.03 (13)
C11—C6—C7—C8	−0.7 (2)	C11'—C6'—C7'—C8'	0.2 (2)
C5—C6—C7—C8	−179.97 (13)	C5'—C6'—C7'—C8'	180.00 (13)
C6—C7—C8—C9	0.1 (2)	C6'—C7'—C8'—C9'	−0.7 (2)
C12—O2—C9—C8	176.35 (13)	C12'—O2'—C9'—C10'	−2.1 (2)
C12—O2—C9—C10	−3.6 (2)	C12'—O2'—C9'—C8'	177.49 (13)
C7—C8—C9—O2	−179.13 (12)	C7'—C8'—C9'—O2'	−178.38 (12)
C7—C8—C9—C10	0.8 (2)	C7'—C8'—C9'—C10'	1.2 (2)
O2—C9—C10—C11	178.93 (13)	O2'—C9'—C10'—C11'	178.20 (13)
C8—C9—C10—C11	−1.0 (2)	C8'—C9'—C10'—C11'	−1.4 (2)
C9—C10—C11—C6	0.4 (2)	C9'—C10'—C11'—C6'	1.0 (2)
C7—C6—C11—C10	0.5 (2)	C7'—C6'—C11'—C10'	−0.4 (2)
C5—C6—C11—C10	179.72 (13)	C5'—C6'—C11'—C10'	179.86 (13)
C9—O2—C12—C13	−174.97 (12)	C9'—O2'—C12'—C13'	−173.82 (13)
C2—N1—C14—C19	−50.0 (2)	C2'—N1'—C14'—C19'	−60.2 (2)
C2—N1—C14—C15	131.93 (18)	C2'—N1'—C14'—C15'	122.06 (18)
C19—C14—C15—C16	0.3 (3)	C19'—C14'—C15'—C16'	0.9 (3)
N1—C14—C15—C16	178.35 (18)	N1'—C14'—C15'—C16'	178.60 (16)
C14—C15—C16—C17	1.6 (3)	C14'—C15'—C16'—C17'	0.4 (3)
C15—C16—C17—C18	−2.2 (3)	C20'—O3'—C17'—C16'	−179.90 (16)
C15—C16—C17—O3	178.87 (19)	C20'—O3'—C17'—C18'	−0.1 (3)
C20—O3—C17—C18	0.9 (3)	C15'—C16'—C17'—O3'	179.18 (16)
C20—O3—C17—C16	179.71 (18)	C15'—C16'—C17'—C18'	−0.6 (3)
C16—C17—C18—C19	0.9 (3)	O3'—C17'—C18'—C19'	179.81 (17)
O3—C17—C18—C19	179.73 (17)	C16'—C17'—C18'—C19'	−0.4 (3)
C15—C14—C19—C18	−1.6 (3)	C15'—C14'—C19'—C18'	−2.0 (3)
N1—C14—C19—C18	−179.64 (16)	N1'—C14'—C19'—C18'	−179.66 (15)
C17—C18—C19—C14	1.0 (3)	C17'—C18'—C19'—C14'	1.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H01···S'	0.83 (1)	2.74 (1)	3.4483 (14)	146 (1)
N4—H04···O1'i	0.81 (1)	2.02 (1)	2.8156 (17)	168 (2)
N1'—H01'···Sii	0.82 (1)	2.66 (1)	3.3772 (14)	148 (1)
N4'—H04'···O1i	0.84 (1)	2.01 (1)	2.8228 (18)	164 (2)
C11'—H11'···O1i	0.95	2.41	3.3378 (19)	166
C11—H11···O1'i	0.95	2.38	3.2927 (18)	162
C20—H20B···Siii	0.98	2.98	3.9215 (17)	161
C20'—H20E···S'iv	0.98	2.92	3.8936 (18)	175
C10'—H10'···Si	0.95	2.83	3.7559 (17)	166
C10—H10···S'i	0.95	2.81	3.7369 (17)	166
C15'—H15'···Sii	0.95	3.05	3.6482 (16)	123
C15—H15···S'	0.95	2.94	3.6925 (17)	137
N3'—H03'···Cg	0.85 (1)	2.53	3.25	144
N3—H03···Cg'v	0.82 (1)	2.65	3.29	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H01⋯S′	0.826 (11)	2.735 (12)	3.4483 (14)	145.5 (14)
N4—H04⋯O1′i	0.812 (12)	2.016 (13)	2.8156 (17)	168.2 (17)
N1′—H01′⋯Sii	0.816 (11)	2.659 (12)	3.3772 (14)	147.8 (14)
N4′—H04′⋯O1i	0.836 (12)	2.011 (13)	2.8228 (18)	163.7 (15)
C11′—H11′⋯O1i	0.95	2.41	3.3378 (19)	166
C11—H11⋯O1′i	0.95	2.38	3.2927 (18)	162
C20—H20B⋯Siii	0.98	2.98	3.9215 (17)	161
C20′—H20E⋯S′iv	0.98	2.92	3.8936 (18)	175
C10′—H10′⋯Si	0.95	2.83	3.7559 (17)	166
C10—H10⋯S′i	0.95	2.81	3.7369 (17)	166
C15′—H15′⋯Sii	0.95	3.05	3.6482 (16)	123
C15—H15⋯S′	0.95	2.94	3.6925 (17)	137
N3′—H03′⋯Cg	0.847 (10)	2.53	3.25	144
N3—H03⋯Cg′v	0.822 (10)	2.65	3.29	135

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) . Cg is the centroid of the C6–C11 ring and Cg′ is the centroid of the C6′–C11′ ring.