Ethyl 4-(2,5-di­methyl­phen­yl)-6-methyl-2-sulfanyl­idene-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate

R, S.; Begum, N.S.

doi:10.1107/S2414314617014407

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 10| October 2017| x171440

https://doi.org/10.1107/S2414314617014407

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Ethyl 4-(2,5-dimethylphenyl)-6-methyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Shashi R ^a and Noor Shahina Begum ^a ^*

^aDepartment of Studies in Chemistry, Central College Campus, Bangalore University, Bangalore 560 001, Karnataka, India
^*Correspondence e-mail: noorsb@rediffmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 6 September 2017; accepted 6 October 2017; online 13 October 2017)

The title compound, C₁₆H₂₀N₂O₂S, crystallizes with two molecules in the asymmetric unit, one of which shows positional disorder of the ethyl side chain over two orientations in a 0.555 (7):0.445 (7) ratio. The hydropyrimidine ring adopts a shallow boat conformation and the 2,5-dimethylphenyl ring is positioned axially. The crystal structure features N—H⋯S, N—H⋯O and C—H⋯O hydrogen bonds, which link the molecules into (10-1) sheets.

Keywords: crystal structure; DHPM derivative; hydrogen bonding.

CCDC reference: 1578486

Structure description

Dihydropyrimidine (DHPM) derivatives are used as calcium channel blockers (Zorkun et al., 2006 ) and inhibitors of mitotic kinesin Eg5 for treating cancer (Cochran et al., 2005 ). As part of our studies of DHPM derivatives, the title compound, C₁₄H₁₄F₄N₂O₃S, was isolated and the structure determined by X-ray diffraction. The molecular structure of the compound is shown in Fig. 1. The title compound crystallizes with two molecules (A and B) in the asymmetric unit. The 2,5-dimethyl phenyl ring subtends dihedral angles with the pyrimidine ring of 88.7 (1) and 88.75 (1)° for A and B, respectively. The pyrimidine ring adopts a boat conformation with atoms N2 and C6 displaced by 0.130 (3) and 0.279 (8) Å, respectively, from the mean plane of the other four atoms (C2/C4/C5/N1) in molecule A. Similarly, the pyrimidine ring of molecule B adopts a boat conformation with atoms N2′ and C6′ displaced by 0.110 (4) and 0.325 (8) Å, respectively, from the mean plane of the other four atoms (C2′/C4′/C5′/N1′).

Figure 1
The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level.

The crystal structure features N—H⋯S, N–H⋯O and C—H⋯O hydrogen bonds (Table 1), which link the molecules into (10 $[\overline{1}]$ ) sheets incorporating R₂²(8) loops (Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1ⁱ	0.88	2.47	3.315 (2)	160
N1′—H1′⋯S1	0.88	2.49	3.316 (2)	156
N2—H2⋯S2	0.88	2.65	3.431 (2)	148
N2′—H2′⋯O2ⁱⁱ	0.88	1.97	2.833 (3)	168
C1—H1C⋯O2′ⁱⁱⁱ	0.98	2.58	3.477 (5)	152
C1′—H1′2⋯O2ⁱⁱ	0.98	2.56	3.377 (4)	141
C16—H16A⋯S1ⁱ	0.98	2.77	3.717 (3)	162
Symmetry codes: (i) -x, -y+2, -z; (ii) $[-x-{\script{1\over 2}}, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Figure 2
Unit-cell packing of the title compound, showing N2—H2⋯S2 and N1—H1⋯S1 interactions as dotted lines. H atoms not involved in hydrogen bonding have been excluded.

Synthesis and crystallization

A mixture of 2,5-dimethylbenzaldehydes (10 mmol), thiourea (10 mmol), ethyl acetoacetate (10 mmol) and a catalytic amount of concentrated hydrochloric acid in ethanol (20 ml) was refluxed for 8 h (Fig. 3). The reaction mixture was allowed to stand overnight at room temperature. The solid thus separated was neutralized by using aqueous sodium carbonate solution and the obtained precipitate was filtered and washed with a mixture of ethanol and water (1:1) and recrystallized from N,N-dimethylformamide solution yielding pale-yellow blocks of the title compound (Yield: 84%; m.p. 423–425 K) IR (KBr) ν cm⁻¹: 3298, 3174 (NH), 2982 (CH), 1702 (C=O), 1596 (C=C), 1567 (C=N). ¹H NMR (500 MHz, DMSO-d₆) d: 8.95 (s, 1H), 8.05 (s, 1H), 6.80–6.90 (m, 3H), 5.45 (s, 1H), 3.85 (q, 2H), 2.30 (s, 6H), 2.20 (s, 3H), 0.97 (t, 3H). Mass (m/z): 304 M, 305 M⁺, 199 (base peak), 231, 171.

Figure 3
The reaction scheme for the preparation of the title compound.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₆H₂₀N₂O₂S
M_r	304.40
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	14.4124 (7), 14.9172 (6), 15.1412 (6)
β (°)	100.377 (1)
V (Å³)	3202.0 (2)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.21
Crystal size (mm)	0.15 × 0.15 × 0.14

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Bruker, 1998 )
T_min, T_max	0.969, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	25239, 5637, 4227
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.146, 0.78
No. of reflections	5637
No. of parameters	407
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.34
Computer programs: SMART and SAINT-Plus (Bruker, 1998), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ) and CAMERON (Watkin et al., 1996 ).

Structural data

CCDC reference: 1578486

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314617014407/hb4170sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617014407/hb4170Isup2.hkl

IR Spectra. DOI: https://doi.org/10.1107/S2414314617014407/hb4170sup3.pdf

Proton NMR Spectra. DOI: https://doi.org/10.1107/S2414314617014407/hb4170sup4.tif

Mass Spectra. DOI: https://doi.org/10.1107/S2414314617014407/hb4170sup5.docx

checkCIF report

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

Ethyl 4-(2,5-dimethylphenyl)-6-methyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidine-5-carboxylate top

Crystal data top

C₁₆H₂₀N₂O₂S	F(000) = 1296
M_r = 304.40	D_x = 1.263 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 14.4124 (7) Å	Cell parameters from 5637 reflections
b = 14.9172 (6) Å	θ = 2.0–25.0°
c = 15.1412 (6) Å	µ = 0.21 mm⁻¹
β = 100.377 (1)°	T = 100 K
V = 3202.0 (2) Å³	Block, pale yellow
Z = 8	0.15 × 0.15 × 0.14 mm

Data collection top

Bruker SMART APEX CCD diffractometer	4227 reflections with I > 2σ(I)
ω scans	R_int = 0.049
Absorption correction: multi-scan (SADABS; Bruker, 1998)	θ_max = 25.0°, θ_min = 2.0°
T_min = 0.969, T_max = 0.971	h = −17→17
25239 measured reflections	k = −17→17
5637 independent reflections	l = −17→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.049	H-atom parameters constrained
wR(F²) = 0.146	w = 1/[σ²(F_o²) + (0.090P)² + 7.9246P] where P = (F_o² + 2F_c²)/3
S = 0.78	(Δ/σ)_max = 0.001
5637 reflections	Δρ_max = 0.51 e Å⁻³
407 parameters	Δρ_min = −0.34 e Å⁻³
0 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles,correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.00143 (5)	0.85136 (5)	0.03650 (4)	0.02149 (19)
S2	−0.12626 (5)	0.60299 (5)	−0.02637 (5)	0.0300 (2)
O1	−0.20098 (14)	0.83962 (13)	−0.39604 (12)	0.0256 (5)
O2	−0.13530 (14)	0.97632 (13)	−0.38361 (13)	0.0271 (5)
N2'	−0.30632 (16)	0.63422 (15)	−0.01800 (16)	0.0237 (5)
H2'	−0.3173	0.5816	−0.0440	0.028*
N1	−0.02760 (15)	0.94157 (15)	−0.11651 (14)	0.0194 (5)
H1	−0.0160	0.9892	−0.0821	0.023*
N2	−0.06218 (16)	0.79254 (15)	−0.12882 (14)	0.0211 (5)
H2	−0.0544	0.7385	−0.1053	0.025*
C2	−0.03058 (18)	0.86416 (18)	−0.07630 (18)	0.0190 (6)
C5	−0.10039 (19)	0.87969 (18)	−0.26024 (18)	0.0196 (6)
N1'	−0.20635 (16)	0.75143 (15)	0.02123 (15)	0.0235 (5)
H1'	−0.1486	0.7701	0.0420	0.028*
C4	−0.10644 (19)	0.80106 (18)	−0.21849 (18)	0.0224 (6)
C6	−0.04177 (19)	0.95575 (18)	−0.21342 (17)	0.0196 (6)
H6	−0.0778	1.0128	−0.2276	0.024*
C6'	−0.2839 (2)	0.81632 (19)	0.02050 (19)	0.0242 (6)
H6'	−0.2666	0.8567	0.0736	0.029*
C14'	−0.25847 (19)	0.96154 (18)	−0.0615 (2)	0.0224 (6)
C1'	−0.4641 (2)	0.6189 (2)	0.0127 (2)	0.0292 (7)
H1'1	−0.4559	0.5894	0.0715	0.044*
H1'2	−0.4688	0.5734	−0.0346	0.044*
H1'3	−0.5219	0.6549	0.0037	0.044*
C3	−0.14684 (19)	0.90319 (18)	−0.35165 (18)	0.0214 (6)
C10'	−0.3412 (2)	0.8390 (2)	−0.1455 (2)	0.0293 (7)
H10'	−0.3662	0.7800	−0.1464	0.035*
O1'	−0.41751 (19)	0.89949 (17)	0.0866 (2)	0.0715 (10)
C5'	−0.3723 (2)	0.76588 (19)	0.03087 (19)	0.0266 (7)
C11	0.1992 (2)	0.8927 (2)	−0.2667 (2)	0.0312 (7)
C9'	−0.29503 (19)	0.87409 (18)	−0.0645 (2)	0.0232 (6)
C9	0.0534 (2)	0.96553 (19)	−0.24365 (18)	0.0224 (6)
C10	0.1109 (2)	0.8900 (2)	−0.24104 (18)	0.0246 (6)
H10	0.0892	0.8348	−0.2211	0.030*
C16'	−0.2128 (2)	1.00512 (19)	0.0250 (2)	0.0286 (7)
H2'1	−0.1864	1.0632	0.0121	0.043*
H2'2	−0.1623	0.9665	0.0560	0.043*
H2'3	−0.2601	1.0141	0.0633	0.043*
C2'	−0.2169 (2)	0.66710 (19)	−0.00703 (18)	0.0238 (6)
C4'	−0.3815 (2)	0.6781 (2)	0.00902 (18)	0.0244 (6)
C7	−0.2443 (2)	0.8619 (2)	−0.48809 (19)	0.0302 (7)
H7A	−0.1962	0.8847	−0.5216	0.036*
H7B	−0.2932	0.9086	−0.4885	0.036*
C1	−0.1571 (2)	0.7181 (2)	−0.2567 (2)	0.0331 (7)
H1A	−0.2253	0.7288	−0.2671	0.050*
H1B	−0.1415	0.6684	−0.2143	0.050*
H1C	−0.1377	0.7029	−0.3136	0.050*
C16	0.0274 (2)	1.1324 (2)	−0.2750 (2)	0.0333 (7)
H16A	0.0249	1.1514	−0.2135	0.050*
H16B	−0.0367	1.1215	−0.3076	0.050*
H16C	0.0570	1.1797	−0.3054	0.050*
C12'	−0.3134 (2)	0.9720 (2)	−0.2225 (2)	0.0290 (7)
H12'	−0.3183	1.0060	−0.2762	0.035*
C14	0.0843 (2)	1.0479 (2)	−0.27263 (19)	0.0272 (7)
C13	0.1725 (2)	1.0494 (2)	−0.2994 (2)	0.0348 (8)
H13	0.1948	1.1043	−0.3197	0.042*
O2'	−0.5221 (2)	0.78754 (19)	0.0748 (3)	0.0772 (11)
C11'	−0.3520 (2)	0.8869 (2)	−0.2253 (2)	0.0304 (7)
C13'	−0.2677 (2)	1.0080 (2)	−0.1422 (2)	0.0290 (7)
H13'	−0.2418	1.0665	−0.1422	0.035*
C8	−0.2873 (3)	0.7777 (2)	−0.5298 (2)	0.0446 (9)
H8A	−0.2381	0.7322	−0.5288	0.067*
H8B	−0.3174	0.7896	−0.5920	0.067*
H8C	−0.3347	0.7560	−0.4959	0.067*
C15'	−0.4070 (3)	0.8492 (2)	−0.3117 (2)	0.0433 (9)
H3'1	−0.4013	0.8895	−0.3615	0.065*
H3'2	−0.4736	0.8435	−0.3067	0.065*
H3'3	−0.3819	0.7901	−0.3230	0.065*
C15	0.2608 (2)	0.8103 (3)	−0.2595 (2)	0.0421 (9)
H15A	0.2970	0.8056	−0.1983	0.063*
H15B	0.3043	0.8149	−0.3021	0.063*
H15C	0.2212	0.7570	−0.2732	0.063*
C12	0.2280 (2)	0.9737 (2)	−0.2972 (2)	0.0366 (8)
H12	0.2868	0.9772	−0.3170	0.044*
C3'	−0.4458 (3)	0.8152 (2)	0.0651 (3)	0.0499 (10)
C7A'	−0.4956 (5)	0.9670 (5)	0.0962 (8)	0.059 (2)	0.555 (7)
H7A1	−0.5440	0.9687	0.0408	0.071*	0.555 (7)
H7A2	−0.5264	0.9508	0.1474	0.071*	0.555 (7)
C8A'	−0.4474 (4)	1.0547 (4)	0.1120 (5)	0.050 (2)	0.555 (7)
H8A1	−0.3936	1.0492	0.1615	0.075*	0.555 (7)
H8A2	−0.4917	1.0994	0.1274	0.075*	0.555 (7)
H8A3	−0.4251	1.0735	0.0575	0.075*	0.555 (7)
C7B'	−0.4663 (6)	0.9414 (5)	0.1581 (6)	0.0317 (19)	0.445 (7)
H7B1	−0.4485	1.0055	0.1617	0.038*	0.445 (7)
H7B2	−0.5349	0.9392	0.1343	0.038*	0.445 (7)
C8B'	−0.4528 (5)	0.9071 (6)	0.2546 (6)	0.043 (2)	0.445 (7)
H8B1	−0.4764	0.8455	0.2548	0.065*	0.445 (7)
H8B2	−0.4877	0.9455	0.2897	0.065*	0.445 (7)
H8B3	−0.3856	0.9082	0.2811	0.065*	0.445 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0266 (4)	0.0218 (4)	0.0167 (3)	−0.0018 (3)	0.0055 (3)	−0.0007 (3)
S2	0.0321 (4)	0.0230 (4)	0.0364 (4)	0.0024 (3)	0.0098 (3)	0.0027 (3)
O1	0.0309 (11)	0.0270 (11)	0.0181 (10)	−0.0065 (9)	0.0018 (8)	0.0002 (9)
O2	0.0308 (11)	0.0222 (11)	0.0274 (11)	−0.0013 (9)	0.0027 (9)	0.0056 (9)
N2'	0.0287 (13)	0.0192 (12)	0.0243 (13)	−0.0049 (10)	0.0079 (10)	−0.0017 (10)
N1	0.0256 (12)	0.0169 (12)	0.0169 (12)	−0.0017 (9)	0.0071 (9)	−0.0031 (10)
N2	0.0316 (13)	0.0152 (11)	0.0168 (12)	0.0004 (10)	0.0050 (10)	0.0010 (10)
C2	0.0179 (13)	0.0200 (14)	0.0204 (14)	0.0008 (11)	0.0070 (11)	−0.0023 (12)
C5	0.0225 (14)	0.0189 (14)	0.0184 (14)	−0.0010 (11)	0.0063 (11)	−0.0029 (12)
N1'	0.0250 (13)	0.0228 (13)	0.0239 (13)	−0.0058 (10)	0.0074 (10)	−0.0033 (10)
C4	0.0276 (15)	0.0203 (14)	0.0209 (14)	−0.0030 (12)	0.0084 (12)	−0.0030 (12)
C6	0.0274 (15)	0.0158 (13)	0.0161 (14)	0.0006 (11)	0.0049 (11)	0.0004 (11)
C6'	0.0288 (15)	0.0207 (14)	0.0259 (15)	−0.0053 (12)	0.0119 (12)	−0.0054 (13)
C14'	0.0159 (14)	0.0205 (14)	0.0316 (16)	0.0027 (11)	0.0063 (12)	0.0011 (12)
C1'	0.0311 (16)	0.0266 (16)	0.0307 (17)	−0.0075 (13)	0.0077 (13)	0.0010 (13)
C3	0.0219 (14)	0.0221 (15)	0.0214 (15)	0.0016 (11)	0.0072 (11)	−0.0015 (12)
C10'	0.0396 (18)	0.0244 (15)	0.0285 (17)	−0.0106 (13)	0.0181 (14)	−0.0056 (14)
O1'	0.0527 (17)	0.0398 (15)	0.140 (3)	−0.0169 (13)	0.0657 (19)	−0.0429 (17)
C5'	0.0310 (16)	0.0253 (16)	0.0264 (16)	−0.0050 (12)	0.0128 (13)	−0.0003 (13)
C11	0.0276 (16)	0.0446 (19)	0.0212 (15)	0.0020 (14)	0.0040 (12)	−0.0039 (14)
C9'	0.0226 (15)	0.0207 (14)	0.0295 (16)	0.0010 (11)	0.0129 (12)	−0.0039 (12)
C9	0.0282 (15)	0.0249 (15)	0.0138 (14)	−0.0062 (12)	0.0034 (11)	−0.0012 (12)
C10	0.0273 (16)	0.0288 (16)	0.0180 (14)	−0.0021 (12)	0.0046 (12)	−0.0005 (12)
C16'	0.0282 (16)	0.0177 (14)	0.0386 (18)	−0.0026 (12)	0.0030 (13)	0.0005 (13)
C2'	0.0316 (16)	0.0238 (15)	0.0162 (14)	−0.0030 (12)	0.0052 (12)	0.0039 (12)
C4'	0.0300 (16)	0.0274 (16)	0.0171 (14)	−0.0040 (12)	0.0077 (12)	0.0031 (12)
C7	0.0302 (16)	0.0400 (18)	0.0194 (15)	−0.0028 (14)	0.0021 (12)	0.0006 (14)
C1	0.050 (2)	0.0220 (15)	0.0257 (16)	−0.0104 (14)	0.0039 (14)	−0.0001 (13)
C16	0.050 (2)	0.0264 (16)	0.0251 (16)	−0.0083 (14)	0.0100 (14)	0.0013 (13)
C12'	0.0326 (17)	0.0257 (16)	0.0315 (17)	0.0061 (13)	0.0133 (13)	0.0064 (14)
C14	0.0345 (17)	0.0302 (16)	0.0166 (14)	−0.0075 (13)	0.0042 (12)	0.0007 (13)
C13	0.0389 (19)	0.0416 (19)	0.0249 (16)	−0.0154 (15)	0.0084 (14)	0.0032 (15)
O2'	0.0587 (18)	0.0531 (17)	0.139 (3)	−0.0233 (14)	0.069 (2)	−0.0380 (19)
C11'	0.0317 (17)	0.0310 (17)	0.0316 (17)	−0.0010 (13)	0.0136 (13)	−0.0023 (14)
C13'	0.0251 (16)	0.0206 (15)	0.0420 (19)	0.0016 (12)	0.0085 (13)	0.0033 (14)
C8	0.058 (2)	0.052 (2)	0.0238 (17)	−0.0221 (18)	0.0064 (16)	−0.0058 (16)
C15'	0.055 (2)	0.049 (2)	0.0278 (18)	−0.0102 (17)	0.0109 (16)	−0.0017 (16)
C15	0.0326 (18)	0.060 (2)	0.0347 (19)	0.0101 (16)	0.0073 (14)	−0.0096 (17)
C12	0.0258 (17)	0.058 (2)	0.0282 (17)	−0.0070 (15)	0.0093 (13)	−0.0019 (16)
C3'	0.046 (2)	0.038 (2)	0.077 (3)	−0.0149 (17)	0.039 (2)	−0.0178 (19)
C7A'	0.042 (4)	0.052 (5)	0.091 (7)	0.007 (4)	0.033 (5)	−0.015 (5)
C8A'	0.035 (4)	0.037 (4)	0.080 (5)	0.009 (3)	0.015 (3)	−0.023 (4)
C7B'	0.030 (4)	0.022 (4)	0.047 (5)	0.005 (3)	0.016 (4)	−0.008 (4)
C8B'	0.032 (4)	0.050 (5)	0.051 (5)	−0.005 (4)	0.012 (4)	−0.011 (4)

Geometric parameters (Å, º) top

S1—C2	1.698 (3)	C10—H10	0.9500
S2—C2'	1.687 (3)	C16'—H2'1	0.9800
O1—C3	1.331 (3)	C16'—H2'2	0.9800
O1—C7	1.459 (3)	C16'—H2'3	0.9800
O2—C3	1.217 (3)	C7—C8	1.489 (4)
N2'—C2'	1.361 (4)	C7—H7A	0.9900
N2'—C4'	1.389 (4)	C7—H7B	0.9900
N2'—H2'	0.8800	C1—H1A	0.9800
N1—C2	1.310 (3)	C1—H1B	0.9800
N1—C6	1.460 (3)	C1—H1C	0.9800
N1—H1	0.8800	C16—C14	1.501 (4)
N2—C2	1.360 (3)	C16—H16A	0.9800
N2—C4	1.398 (3)	C16—H16B	0.9800
N2—H2	0.8800	C16—H16C	0.9800
C5—C4	1.343 (4)	C12'—C13'	1.382 (4)
C5—C3	1.467 (4)	C12'—C11'	1.383 (4)
C5—C6	1.513 (4)	C12'—H12'	0.9500
N1'—C2'	1.328 (4)	C14—C13	1.403 (4)
N1'—C6'	1.477 (4)	C13—C12	1.381 (5)
N1'—H1'	0.8800	C13—H13	0.9500
C4—C1	1.499 (4)	O2'—C3'	1.208 (4)
C6—C9	1.529 (4)	C11'—C15'	1.512 (5)
C6—H6	1.0000	C13'—H13'	0.9500
C6'—C5'	1.511 (4)	C8—H8A	0.9800
C6'—C9'	1.533 (4)	C8—H8B	0.9800
C6'—H6'	1.0000	C8—H8C	0.9800
C14'—C13'	1.391 (4)	C15'—H3'1	0.9800
C14'—C9'	1.405 (4)	C15'—H3'2	0.9800
C14'—C16'	1.503 (4)	C15'—H3'3	0.9800
C1'—C4'	1.492 (4)	C15—H15A	0.9800
C1'—H1'1	0.9800	C15—H15B	0.9800
C1'—H1'2	0.9800	C15—H15C	0.9800
C1'—H1'3	0.9800	C12—H12	0.9500
C10'—C11'	1.388 (4)	C7A'—C8A'	1.479 (10)
C10'—C9'	1.389 (4)	C7A'—H7A1	0.9900
C10'—H10'	0.9500	C7A'—H7A2	0.9900
O1'—C3'	1.344 (4)	C8A'—H8A1	0.9800
O1'—C7B'	1.527 (7)	C8A'—H8A2	0.9800
O1'—C7A'	1.536 (7)	C8A'—H8A3	0.9800
C5'—C4'	1.351 (4)	C7B'—C8B'	1.527 (12)
C5'—C3'	1.459 (4)	C7B'—H7B1	0.9900
C11—C12	1.383 (5)	C7B'—H7B2	0.9900
C11—C10	1.397 (4)	C8B'—H8B1	0.9800
C11—C15	1.508 (5)	C8B'—H8B2	0.9800
C9—C10	1.395 (4)	C8B'—H8B3	0.9800
C9—C14	1.404 (4)

C3—O1—C7	115.5 (2)	C8—C7—H7A	110.4
C2'—N2'—C4'	124.5 (2)	O1—C7—H7B	110.4
C2'—N2'—H2'	117.8	C8—C7—H7B	110.4
C4'—N2'—H2'	117.8	H7A—C7—H7B	108.6
C2—N1—C6	125.8 (2)	C4—C1—H1A	109.5
C2—N1—H1	117.1	C4—C1—H1B	109.5
C6—N1—H1	117.1	H1A—C1—H1B	109.5
C2—N2—C4	122.8 (2)	C4—C1—H1C	109.5
C2—N2—H2	118.6	H1A—C1—H1C	109.5
C4—N2—H2	118.6	H1B—C1—H1C	109.5
N1—C2—N2	117.1 (2)	C14—C16—H16A	109.5
N1—C2—S1	122.8 (2)	C14—C16—H16B	109.5
N2—C2—S1	120.1 (2)	H16A—C16—H16B	109.5
C4—C5—C3	126.5 (3)	C14—C16—H16C	109.5
C4—C5—C6	120.9 (2)	H16A—C16—H16C	109.5
C3—C5—C6	112.6 (2)	H16B—C16—H16C	109.5
C2'—N1'—C6'	125.1 (2)	C13'—C12'—C11'	120.6 (3)
C2'—N1'—H1'	117.4	C13'—C12'—H12'	119.7
C6'—N1'—H1'	117.4	C11'—C12'—H12'	119.7
C5—C4—N2	118.7 (2)	C13—C14—C9	117.4 (3)
C5—C4—C1	127.4 (3)	C13—C14—C16	119.9 (3)
N2—C4—C1	113.9 (2)	C9—C14—C16	122.7 (3)
N1—C6—C5	109.1 (2)	C12—C13—C14	122.0 (3)
N1—C6—C9	110.1 (2)	C12—C13—H13	119.0
C5—C6—C9	112.7 (2)	C14—C13—H13	119.0
N1—C6—H6	108.2	C12'—C11'—C10'	117.7 (3)
C5—C6—H6	108.2	C12'—C11'—C15'	120.9 (3)
C9—C6—H6	108.2	C10'—C11'—C15'	121.4 (3)
N1'—C6'—C5'	108.9 (2)	C12'—C13'—C14'	122.3 (3)
N1'—C6'—C9'	109.8 (2)	C12'—C13'—H13'	118.8
C5'—C6'—C9'	113.9 (2)	C14'—C13'—H13'	118.8
N1'—C6'—H6'	108.0	C7—C8—H8A	109.5
C5'—C6'—H6'	108.0	C7—C8—H8B	109.5
C9'—C6'—H6'	108.0	H8A—C8—H8B	109.5
C13'—C14'—C9'	117.3 (3)	C7—C8—H8C	109.5
C13'—C14'—C16'	120.5 (3)	H8A—C8—H8C	109.5
C9'—C14'—C16'	122.2 (3)	H8B—C8—H8C	109.5
C4'—C1'—H1'1	109.5	C11'—C15'—H3'1	109.5
C4'—C1'—H1'2	109.5	C11'—C15'—H3'2	109.5
H1'1—C1'—H1'2	109.5	H3'1—C15'—H3'2	109.5
C4'—C1'—H1'3	109.5	C11'—C15'—H3'3	109.5
H1'1—C1'—H1'3	109.5	H3'1—C15'—H3'3	109.5
H1'2—C1'—H1'3	109.5	H3'2—C15'—H3'3	109.5
O2—C3—O1	123.2 (3)	C11—C15—H15A	109.5
O2—C3—C5	121.2 (3)	C11—C15—H15B	109.5
O1—C3—C5	115.6 (2)	H15A—C15—H15B	109.5
C11'—C10'—C9'	122.3 (3)	C11—C15—H15C	109.5
C11'—C10'—H10'	118.8	H15A—C15—H15C	109.5
C9'—C10'—H10'	118.8	H15B—C15—H15C	109.5
C3'—O1'—C7B'	113.4 (4)	C13—C12—C11	121.1 (3)
C3'—O1'—C7A'	116.2 (4)	C13—C12—H12	119.5
C4'—C5'—C3'	122.0 (3)	C11—C12—H12	119.5
C4'—C5'—C6'	120.3 (3)	O2'—C3'—O1'	122.2 (3)
C3'—C5'—C6'	117.7 (3)	O2'—C3'—C5'	127.3 (3)
C12—C11—C10	117.4 (3)	O1'—C3'—C5'	110.5 (3)
C12—C11—C15	121.9 (3)	C8A'—C7A'—O1'	105.4 (5)
C10—C11—C15	120.7 (3)	C8A'—C7A'—H7A1	110.7
C10'—C9'—C14'	119.7 (3)	O1'—C7A'—H7A1	110.7
C10'—C9'—C6'	119.4 (2)	C8A'—C7A'—H7A2	110.7
C14'—C9'—C6'	120.9 (3)	O1'—C7A'—H7A2	110.7
C10—C9—C14	119.7 (3)	H7A1—C7A'—H7A2	108.8
C10—C9—C6	118.3 (2)	C7A'—C8A'—H8A1	109.5
C14—C9—C6	122.0 (3)	C7A'—C8A'—H8A2	109.5
C9—C10—C11	122.4 (3)	H8A1—C8A'—H8A2	109.5
C9—C10—H10	118.8	C7A'—C8A'—H8A3	109.5
C11—C10—H10	118.8	H8A1—C8A'—H8A3	109.5
C14'—C16'—H2'1	109.5	H8A2—C8A'—H8A3	109.5
C14'—C16'—H2'2	109.5	C8B'—C7B'—O1'	123.0 (6)
H2'1—C16'—H2'2	109.5	C8B'—C7B'—H7B1	106.6
C14'—C16'—H2'3	109.5	O1'—C7B'—H7B1	106.6
H2'1—C16'—H2'3	109.5	C8B'—C7B'—H7B2	106.6
H2'2—C16'—H2'3	109.5	O1'—C7B'—H7B2	106.6
N1'—C2'—N2'	115.6 (3)	H7B1—C7B'—H7B2	106.5
N1'—C2'—S2	123.1 (2)	C7B'—C8B'—H8B1	109.5
N2'—C2'—S2	121.4 (2)	C7B'—C8B'—H8B2	109.5
C5'—C4'—N2'	118.8 (3)	H8B1—C8B'—H8B2	109.5
C5'—C4'—C1'	127.5 (3)	C7B'—C8B'—H8B3	109.5
N2'—C4'—C1'	113.7 (2)	H8B1—C8B'—H8B3	109.5
O1—C7—C8	106.6 (3)	H8B2—C8B'—H8B3	109.5
O1—C7—H7A	110.4

C6—N1—C2—N2	−9.6 (4)	C14—C9—C10—C11	−0.2 (4)
C6—N1—C2—S1	171.3 (2)	C6—C9—C10—C11	−179.5 (3)
C4—N2—C2—N1	−11.8 (4)	C12—C11—C10—C9	−1.3 (4)
C4—N2—C2—S1	167.3 (2)	C15—C11—C10—C9	177.6 (3)
C3—C5—C4—N2	−175.8 (2)	C6'—N1'—C2'—N2'	−15.3 (4)
C6—C5—C4—N2	3.9 (4)	C6'—N1'—C2'—S2	166.0 (2)
C3—C5—C4—C1	3.6 (5)	C4'—N2'—C2'—N1'	−8.7 (4)
C6—C5—C4—C1	−176.7 (3)	C4'—N2'—C2'—S2	170.1 (2)
C2—N2—C4—C5	14.3 (4)	C3'—C5'—C4'—N2'	−176.1 (3)
C2—N2—C4—C1	−165.2 (3)	C6'—C5'—C4'—N2'	3.7 (4)
C2—N1—C6—C5	24.5 (3)	C3'—C5'—C4'—C1'	1.9 (5)
C2—N1—C6—C9	−99.7 (3)	C6'—C5'—C4'—C1'	−178.3 (3)
C4—C5—C6—N1	−20.8 (3)	C2'—N2'—C4'—C5'	14.1 (4)
C3—C5—C6—N1	159.0 (2)	C2'—N2'—C4'—C1'	−164.1 (3)
C4—C5—C6—C9	101.9 (3)	C3—O1—C7—C8	170.5 (3)
C3—C5—C6—C9	−78.3 (3)	C10—C9—C14—C13	1.1 (4)
C2'—N1'—C6'—C5'	29.5 (4)	C6—C9—C14—C13	−179.7 (3)
C2'—N1'—C6'—C9'	−95.9 (3)	C10—C9—C14—C16	−178.4 (3)
C7—O1—C3—O2	1.9 (4)	C6—C9—C14—C16	0.9 (4)
C7—O1—C3—C5	−177.8 (2)	C9—C14—C13—C12	−0.4 (4)
C4—C5—C3—O2	−178.8 (3)	C16—C14—C13—C12	179.1 (3)
C6—C5—C3—O2	1.5 (4)	C13'—C12'—C11'—C10'	−1.5 (4)
C4—C5—C3—O1	0.9 (4)	C13'—C12'—C11'—C15'	176.3 (3)
C6—C5—C3—O1	−178.8 (2)	C9'—C10'—C11'—C12'	1.1 (4)
N1'—C6'—C5'—C4'	−22.4 (4)	C9'—C10'—C11'—C15'	−176.6 (3)
C9'—C6'—C5'—C4'	100.5 (3)	C11'—C12'—C13'—C14'	−0.1 (4)
N1'—C6'—C5'—C3'	157.5 (3)	C9'—C14'—C13'—C12'	2.0 (4)
C9'—C6'—C5'—C3'	−79.6 (4)	C16'—C14'—C13'—C12'	−176.7 (3)
C11'—C10'—C9'—C14'	0.8 (4)	C14—C13—C12—C11	−1.2 (5)
C11'—C10'—C9'—C6'	−178.6 (3)	C10—C11—C12—C13	2.0 (5)
C13'—C14'—C9'—C10'	−2.3 (4)	C15—C11—C12—C13	−176.9 (3)
C16'—C14'—C9'—C10'	176.4 (3)	C7B'—O1'—C3'—O2'	25.2 (7)
C13'—C14'—C9'—C6'	177.1 (2)	C7A'—O1'—C3'—O2'	−18.2 (8)
C16'—C14'—C9'—C6'	−4.2 (4)	C7B'—O1'—C3'—C5'	−154.5 (5)
N1'—C6'—C9'—C10'	78.3 (3)	C7A'—O1'—C3'—C5'	162.2 (5)
C5'—C6'—C9'—C10'	−44.1 (3)	C4'—C5'—C3'—O2'	−3.2 (7)
N1'—C6'—C9'—C14'	−101.1 (3)	C6'—C5'—C3'—O2'	177.0 (4)
C5'—C6'—C9'—C14'	136.5 (3)	C4'—C5'—C3'—O1'	176.4 (3)
N1—C6—C9—C10	69.9 (3)	C6'—C5'—C3'—O1'	−3.4 (5)
C5—C6—C9—C10	−52.2 (3)	C3'—O1'—C7A'—C8A'	−175.3 (6)
N1—C6—C9—C14	−109.4 (3)	C3'—O1'—C7B'—C8B'	65.6 (8)
C5—C6—C9—C14	128.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1ⁱ	0.88	2.47	3.315 (2)	160
N1′—H1′···S1	0.88	2.49	3.316 (2)	156
N2—H2···S2	0.88	2.65	3.431 (2)	148
N2′—H2′···O2ⁱⁱ	0.88	1.97	2.833 (3)	168
C1—H1C···O2′ⁱⁱⁱ	0.98	2.58	3.477 (5)	152
C1′—H1′2···O2ⁱⁱ	0.98	2.56	3.377 (4)	141
C16—H16A···S1ⁱ	0.98	2.77	3.717 (3)	162

Symmetry codes: (i) −x, −y+2, −z; (ii) −x−1/2, y−1/2, −z−1/2; (iii) x+1/2, −y+3/2, z−1/2.

References

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