Morpholin-4-ium [5-cyano-6-(4-methyl­phen­yl)-4-(morpholin-4-yl)pyrimidin-2-yl](phenyl­sulfon­yl)amide

Mohamed-Ezzat, R.A.; Kariuki, B.M.; Azzam, R.A.

doi:10.1107/S2414314622010331

organic compounds

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ISSN: 2414-3146

Volume 7| Part 11| November 2022| x221033

https://doi.org/10.1107/S2414314622010331

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Morpholin-4-ium [5-cyano-6-(4-methylphenyl)-4-(morpholin-4-yl)pyrimidin-2-yl](phenylsulfonyl)amide

Reham A. Mohamed-Ezzat,^a Benson M. Kariuki ^b and Rasha A. Azzam ^c ^*

^aChemistry of Natural & Microbial Products Department, National Research Center, Cairo, Egypt, ^bSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10, 3AT, United Kingdom, and ^cDepartment of Chemistry, Helwan University, Cairo, Egypt
^*Correspondence e-mail: rashaazzam8@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 24 October 2022; accepted 25 October 2022; online 1 November 2022)

In the title molecular salt, C₄H₁₀NO⁺·C₂₂H₂₀N₅O₂S⁻, pairs of anions are linked by pairs of morpholinium cations through N—H⋯N and bifurcated N—H⋯(O,N) hydrogen bonds. Every cation donates two such bonds, one to each of the neighbouring pair of cations, generating centrosymmetric tetramers.

Keywords: crystal structure; synthesis; sulfonamide; X-ray diffraction.

CCDC reference: 2180058

Structure description

Sulfonamides were pioneering medications for the treatment of bacterial infections and, despite the subsequent introduction of penicillin, they are still used as antibiotics (Gulçin & Taslimi, 2018 ). As part of our ongoing studies in this area (Elgemeie et al., 2015a ,b , 2019 ; Azzam et al., 2019 , 2017 ; Mohamed-Ezzat et al., 2021 ), the structure of the title compound is now described: it crystallizes as a molecular salt comprising morpholin-4-ium (C₄H₁₀NO⁺) cations and (benzenesulfonyl)[5-cyano-4-(morpholin-4-yl)-6-phenylpyrimidin-2-yl]azanide 5(–H) (C₂₂H₂₀N₅O₂S⁻) anions (Fig. 1). The sulfonamide group is deprotonated in contrast to other crystal structures containing the N-(pyrimidin-2-yl)benzenesulfonamide moiety, which are protonated (Singh & Baruah, 2019 ; Basak et al., 1983 ): the morpholine reagent used in the last step of the synthesis accepts a proton to form the counter-ion.

Figure 1
The asymmetric unit of 5 showing 50% probability displacement ellipsoids.

In the pyrimidine ring of the anion, the longest C—N bond is C7—N2 [1.370 (2) Å], which is located opposite the longest C—C bond [C8—C9 = 1.431 (2) Å]. The other N—C bonds lie in the range 1.330 (2)–1.339 (2) Å. One phenyl ring (C1–C6) is almost perpendicular to the plane of the pyrimidine ring (N2/N3/C7–C10): the dihedral angle of 84.84 (6)° is enabled by a twist in the sulfonamide group as illustrated by the C7—N1—S1—C1 torsion angle of 63.74 (15)°. The angle between the second phenyl group (C16–C21) and the pyrimidine ring is 48.19 (7)°. The two H atoms attached to the nitrogen atom of the morpholin-4-ium ion are involved in intermolecular N—H⋯N and N—H⋯(O,N) hydrogen bonds (Table 1) to the anion (Fig. 2). N2 is an acceptor of one contact whereas the other contact is bifurcated to O1 and N1. Thus, two anions adjacent to the cation are bridged through hydrogen bonding to generate centrosymmetric tetramers.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6A⋯O1ⁱ	0.89	2.45	3.113 (2)	131
N6—H6A⋯N1ⁱ	0.89	2.19	3.059 (2)	165
N6—H6B⋯N2	0.89	1.95	2.831 (2)	171
Symmetry code: (i) .

Figure 2
A segment of the crystal structure showing a tetramer of two anions and two cations with hydrogen bonds shown as red dashed lines.

Synthesis and crystallization

N-[5-Cyano-4-(4-methylphenyl)-6-oxo-1,6-dihydropyrimidin-2-yl]benzenesulfonamide, 3, was prepared via a Michael addition by the reaction of N-(diaminomethylidene)benzenesulfonamide, 2, with ethyl (2E)-2-cyano-3-(4-methylphenyl)prop-2-enoate, 1, in the presence of potassium hydroxide, with dioxane as a solvent (Azzam, 2019 ). N-[4-Chloro-5-cyano-6-(4-methylphenyl)pyrimidin-2-yl]benzenesulfonamide, 4, was formed by treating compound 3 with phosphorous oxychloride. Finally, a solution of 4 (0.01 mol) and morpholine (0.03 mmol) in dry dioxane (20 ml) containing potassium hydroxide (0.015 mol) was refluxed for 2 h (Fig. 3). The reaction mixture was cooled and poured onto ice. After 48 hours, the solid product formed was filtered off. Recrystallization from aqueous solution produced the title salt, 5.

Figure 3
Reaction scheme. Reagents and conditions: (i) potassium hydroxide; dioxane; reflux; 2 h, (ii) phosphorus oxychloride; reflux; 1 h, and (iii) morpholine; potassium carbonate; dioxane; reflux; 2 h.

Off-white crystals; yield 69%; m.p. 244–246°C; ¹H NMR (500 MHz, DMSO-d₆): δ 2.35 (s, 3H, CH₃), 3.15–3.18 (m, 4H, 2CH₂), 3.49–3.51 (m, 4H, 2CH₂), 3.56–3.58 (m, 4H, 2CH₂), 3.80–3.83 (m, 4H, 2CH₂), 7.25 (d, J = 8.8 Hz, 2H, Ar—H), 7.41–7.48 (m, 3H, Ar—H), 7.54 (d, J = 8.8 Hz, 2H, Ar—H), 7.78–7.79 (m, 2H, Ar—H), 7.80 (s, 2H, NH₂). Analysis calculated for C₂₆H₃₀N₆O₄S: C 59.75; H 5.79; N 16.08; S 6.14. Found: C 59.69; H 5.75; N 16.20; S 6.19%.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₄H₁₀NO⁺·C₂₂H₂₀N₅O₃S⁻
M_r	522.62
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	10.4177 (4), 11.7104 (3), 21.5388 (7)
β (°)	99.964 (3)
V (Å³)	2588.00 (15)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.17
Crystal size (mm)	0.59 × 0.39 × 0.22

Data collection
Diffractometer	SuperNova, Dual, Cu at home/near, Atlas
Absorption correction	Gaussian (CrysAlis PRO; Rigaku OD, 2021 $[Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.468, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	24156, 6299, 4792
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.695

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.130, 1.07
No. of reflections	6299
No. of parameters	335
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.42
Computer programs: CrysAlis PRO (Rigaku OD, 2021 $[Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXS (Sheldrick, 2008 ), SHELXL (Sheldrick, 2015 ) and ORTEP-3 for Windows (Farrugia, 2012 ).

Structural data

CCDC reference: 2180058

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314622010331/hb4417sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314622010331/hb4417Isup2.hkl

chemical scheme. DOI: https://doi.org/10.1107/S2414314622010331/hb4417sup3.tif

Supporting information file. DOI: https://doi.org/10.1107/S2414314622010331/hb4417Isup4.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2021); cell refinement: CrysAlis PRO (Rigaku OD, 2021); data reduction: CrysAlis PRO (Rigaku OD, 2021); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: ORTEP-3 for Windows (Farrugia, 2012).

Morpholin-4-ium [5-cyano-6-(4-methylphenyl)-4-(morpholin-4-yl)pyrimidin-2-yl](phenylsulfonyl)amide top

Crystal data top

C₄H₁₀NO⁺·C₂₂H₂₀N₅O₃S⁻	F(000) = 1104
M_r = 522.62	D_x = 1.341 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.4177 (4) Å	Cell parameters from 9606 reflections
b = 11.7104 (3) Å	θ = 3.8–28.7°
c = 21.5388 (7) Å	µ = 0.17 mm⁻¹
β = 99.964 (3)°	T = 296 K
V = 2588.00 (15) Å³	Block, colourless
Z = 4	0.59 × 0.39 × 0.22 mm

Data collection top

SuperNova, Dual, Cu at home/near, Atlas diffractometer	4792 reflections with I > 2σ(I)
ω scans	R_int = 0.026
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2021)	θ_max = 29.6°, θ_min = 3.4°
T_min = 0.468, T_max = 1.000	h = −14→13
24156 measured reflections	k = −15→16
6299 independent reflections	l = −29→28

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)] = 0.047	H-atom parameters constrained
wR(F²) = 0.130	w = 1/[σ²(F_o²) + (0.051P)² + 1.057P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
6299 reflections	Δρ_max = 0.25 e Å⁻³
335 parameters	Δρ_min = −0.42 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.

Refinement. Hydrogen atoms were inserted in idealized positions and a riding model was used with U_iso(H) set at 1.2 the values for the C or N to which they are bonded.

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

	x	y	z	U_iso*/U_eq
C1	0.39746 (16)	0.55594 (15)	0.26967 (8)	0.0364 (4)
C2	0.4004 (2)	0.6037 (2)	0.21176 (9)	0.0554 (5)
H2	0.431138	0.677645	0.208445	0.066*
C3	0.3566 (3)	0.5391 (3)	0.15822 (11)	0.0751 (8)
H3	0.355923	0.570912	0.118600	0.090*
C4	0.3144 (2)	0.4296 (3)	0.16295 (12)	0.0723 (8)
H4	0.287794	0.386557	0.126719	0.087*
C5	0.3111 (2)	0.3831 (2)	0.22091 (13)	0.0661 (7)
H5	0.281315	0.308830	0.224035	0.079*
C6	0.3517 (2)	0.44611 (17)	0.27452 (10)	0.0512 (5)
H6	0.348518	0.414928	0.313928	0.061*
C7	0.64862 (16)	0.52093 (14)	0.37849 (7)	0.0329 (4)
C8	0.80885 (17)	0.51091 (14)	0.31695 (8)	0.0338 (4)
C9	0.88299 (16)	0.43727 (14)	0.36271 (8)	0.0339 (4)
C10	0.82690 (16)	0.40889 (14)	0.41528 (8)	0.0338 (4)
C11	0.7780 (2)	0.64082 (18)	0.22731 (10)	0.0513 (5)
H11A	0.728043	0.684328	0.253162	0.062*
H11B	0.717953	0.607433	0.192622	0.062*
C12	0.8723 (3)	0.7172 (2)	0.20250 (13)	0.0690 (7)
H12A	0.824400	0.776570	0.176883	0.083*
H12B	0.928029	0.753801	0.237609	0.083*
C13	1.0217 (3)	0.5704 (3)	0.20295 (15)	0.0853 (9)
H13A	1.080848	0.605144	0.237535	0.102*
H13B	1.073593	0.529160	0.177068	0.102*
C14	0.9353 (2)	0.48884 (19)	0.22871 (10)	0.0526 (5)
H14A	0.882101	0.447882	0.194430	0.063*
H14B	0.987657	0.433602	0.255552	0.063*
C15	1.01574 (18)	0.40786 (16)	0.36277 (9)	0.0408 (4)
C16	0.89636 (17)	0.33313 (15)	0.46580 (8)	0.0365 (4)
C17	0.95107 (19)	0.23040 (16)	0.45184 (9)	0.0443 (4)
H17	0.940804	0.205576	0.410260	0.053*
C18	1.0208 (2)	0.16462 (18)	0.49937 (10)	0.0509 (5)
H18	1.055758	0.095288	0.489394	0.061*
C19	1.0396 (2)	0.20040 (19)	0.56175 (10)	0.0516 (5)
C20	0.9792 (2)	0.29990 (19)	0.57567 (9)	0.0538 (5)
H20	0.986764	0.322991	0.617454	0.065*
C21	0.9077 (2)	0.36606 (17)	0.52859 (9)	0.0455 (4)
H21	0.867217	0.432463	0.538977	0.055*
C22	1.1275 (3)	0.1340 (3)	0.61238 (13)	0.0786 (8)
H22A	1.212050	0.169081	0.620502	0.118*
H22B	1.135534	0.056836	0.598458	0.118*
H22C	1.090822	0.133863	0.650304	0.118*
C23	0.5070 (3)	0.14024 (18)	0.53116 (11)	0.0636 (6)
H23A	0.543086	0.063991	0.537983	0.076*
H23B	0.494986	0.170698	0.571640	0.076*
C24	0.6004 (2)	0.21430 (19)	0.50402 (11)	0.0567 (5)
H24A	0.682757	0.217948	0.532919	0.068*
H24B	0.616321	0.182007	0.464587	0.068*
C25	0.3288 (2)	0.2453 (2)	0.48171 (14)	0.0689 (7)
H25A	0.316172	0.275345	0.522183	0.083*
H25B	0.244099	0.240285	0.454790	0.083*
C26	0.4142 (2)	0.32545 (19)	0.45255 (11)	0.0546 (5)
H26A	0.422374	0.298634	0.410798	0.066*
H26B	0.375257	0.400904	0.448447	0.066*
O1	0.32666 (13)	0.65594 (12)	0.36557 (6)	0.0501 (3)
O2	0.50656 (15)	0.73961 (11)	0.32196 (7)	0.0514 (4)
O3	0.9501 (2)	0.65779 (19)	0.16615 (10)	0.0938 (7)
O4	0.38439 (18)	0.13440 (13)	0.49027 (8)	0.0684 (5)
S1	0.44351 (4)	0.63797 (4)	0.33901 (2)	0.03651 (13)
N1	0.53251 (14)	0.55919 (12)	0.39007 (6)	0.0361 (3)
N2	0.71172 (14)	0.44877 (12)	0.42381 (6)	0.0356 (3)
N3	0.69318 (14)	0.54979 (12)	0.32594 (6)	0.0358 (3)
N4	0.85165 (15)	0.55056 (13)	0.26502 (7)	0.0420 (4)
N5	1.12314 (18)	0.38456 (18)	0.36510 (9)	0.0609 (5)
N6	0.54503 (16)	0.33128 (13)	0.49288 (7)	0.0438 (4)
H6A	0.538585	0.363750	0.529578	0.053*
H6B	0.597821	0.373892	0.474098	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0308 (9)	0.0433 (9)	0.0350 (8)	0.0055 (7)	0.0054 (7)	−0.0001 (7)
C2	0.0581 (13)	0.0678 (13)	0.0411 (10)	−0.0057 (11)	0.0112 (9)	0.0056 (10)
C3	0.0694 (16)	0.122 (2)	0.0347 (11)	−0.0027 (16)	0.0102 (11)	−0.0037 (13)
C4	0.0519 (14)	0.100 (2)	0.0617 (15)	0.0027 (13)	−0.0006 (11)	−0.0382 (15)
C5	0.0566 (14)	0.0577 (13)	0.0773 (17)	−0.0040 (11)	−0.0074 (12)	−0.0182 (12)
C6	0.0500 (12)	0.0493 (11)	0.0509 (11)	−0.0036 (9)	−0.0009 (9)	0.0020 (9)
C7	0.0333 (9)	0.0354 (8)	0.0294 (8)	−0.0023 (7)	0.0041 (6)	−0.0007 (6)
C8	0.0346 (9)	0.0334 (8)	0.0339 (8)	−0.0013 (7)	0.0069 (7)	0.0005 (7)
C9	0.0305 (8)	0.0341 (8)	0.0369 (8)	−0.0008 (7)	0.0053 (7)	0.0010 (7)
C10	0.0336 (9)	0.0328 (8)	0.0334 (8)	−0.0042 (7)	0.0011 (7)	−0.0001 (7)
C11	0.0461 (11)	0.0605 (12)	0.0497 (11)	0.0153 (9)	0.0151 (9)	0.0198 (10)
C12	0.0693 (15)	0.0678 (15)	0.0767 (16)	0.0169 (12)	0.0319 (13)	0.0358 (13)
C13	0.0701 (17)	0.106 (2)	0.0923 (19)	0.0398 (16)	0.0503 (15)	0.0471 (17)
C14	0.0600 (13)	0.0591 (12)	0.0410 (10)	0.0185 (10)	0.0153 (9)	0.0032 (9)
C15	0.0388 (10)	0.0422 (9)	0.0420 (10)	0.0012 (8)	0.0082 (8)	0.0065 (8)
C16	0.0333 (9)	0.0389 (9)	0.0357 (9)	−0.0031 (7)	0.0017 (7)	0.0057 (7)
C17	0.0464 (11)	0.0440 (10)	0.0432 (10)	0.0017 (8)	0.0097 (8)	0.0054 (8)
C18	0.0478 (11)	0.0475 (11)	0.0592 (12)	0.0074 (9)	0.0144 (9)	0.0167 (9)
C19	0.0419 (11)	0.0552 (12)	0.0552 (12)	−0.0031 (9)	0.0013 (9)	0.0230 (10)
C20	0.0596 (13)	0.0596 (13)	0.0378 (10)	−0.0091 (10)	−0.0043 (9)	0.0067 (9)
C21	0.0495 (11)	0.0442 (10)	0.0400 (10)	−0.0004 (8)	0.0004 (8)	0.0007 (8)
C22	0.0641 (16)	0.0932 (19)	0.0734 (17)	0.0086 (14)	−0.0025 (13)	0.0425 (15)
C23	0.0891 (18)	0.0418 (11)	0.0547 (13)	−0.0095 (11)	−0.0024 (12)	−0.0006 (10)
C24	0.0597 (13)	0.0531 (12)	0.0534 (12)	0.0034 (10)	−0.0011 (10)	−0.0020 (10)
C25	0.0554 (14)	0.0606 (14)	0.0907 (18)	−0.0143 (11)	0.0129 (13)	0.0042 (13)
C26	0.0467 (12)	0.0561 (12)	0.0596 (13)	−0.0036 (9)	0.0053 (10)	0.0086 (10)
O1	0.0445 (8)	0.0598 (8)	0.0491 (8)	0.0160 (6)	0.0165 (6)	−0.0027 (6)
O2	0.0632 (9)	0.0348 (7)	0.0568 (8)	−0.0026 (6)	0.0120 (7)	0.0027 (6)
O3	0.0915 (14)	0.1168 (16)	0.0896 (13)	0.0481 (12)	0.0616 (11)	0.0614 (12)
O4	0.0789 (12)	0.0474 (8)	0.0741 (11)	−0.0195 (8)	0.0002 (9)	−0.0010 (8)
S1	0.0395 (2)	0.0355 (2)	0.0353 (2)	0.00451 (17)	0.00866 (17)	−0.00001 (17)
N1	0.0350 (8)	0.0425 (8)	0.0317 (7)	0.0021 (6)	0.0082 (6)	0.0022 (6)
N2	0.0342 (8)	0.0398 (8)	0.0328 (7)	−0.0002 (6)	0.0055 (6)	0.0040 (6)
N3	0.0339 (8)	0.0409 (8)	0.0331 (7)	0.0016 (6)	0.0074 (6)	0.0050 (6)
N4	0.0426 (9)	0.0447 (8)	0.0425 (8)	0.0106 (7)	0.0180 (7)	0.0120 (7)
N5	0.0420 (10)	0.0787 (13)	0.0635 (12)	0.0099 (9)	0.0131 (8)	0.0145 (10)
N6	0.0511 (9)	0.0461 (9)	0.0358 (8)	−0.0075 (7)	0.0116 (7)	0.0019 (7)

Geometric parameters (Å, º) top

C1—C2	1.372 (3)	C14—H14B	0.9700
C1—C6	1.382 (3)	C15—N5	1.144 (2)
C1—S1	1.7708 (17)	C16—C17	1.386 (3)
C2—C3	1.389 (3)	C16—C21	1.392 (3)
C2—H2	0.9300	C17—C18	1.383 (3)
C3—C4	1.365 (4)	C17—H17	0.9300
C3—H3	0.9300	C18—C19	1.389 (3)
C4—C5	1.368 (4)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.381 (3)
C5—C6	1.374 (3)	C19—C22	1.513 (3)
C5—H5	0.9300	C20—C21	1.387 (3)
C6—H6	0.9300	C20—H20	0.9300
C7—N3	1.339 (2)	C21—H21	0.9300
C7—N1	1.353 (2)	C22—H22A	0.9600
C7—N2	1.370 (2)	C22—H22B	0.9600
C8—N3	1.333 (2)	C22—H22C	0.9600
C8—N4	1.356 (2)	C23—O4	1.423 (3)
C8—C9	1.431 (2)	C23—C24	1.495 (3)
C9—C10	1.401 (2)	C23—H23A	0.9700
C9—C15	1.425 (3)	C23—H23B	0.9700
C10—N2	1.330 (2)	C24—N6	1.490 (3)
C10—C16	1.491 (2)	C24—H24A	0.9700
C11—N4	1.466 (2)	C24—H24B	0.9700
C11—C12	1.494 (3)	C25—O4	1.421 (3)
C11—H11A	0.9700	C25—C26	1.504 (3)
C11—H11B	0.9700	C25—H25A	0.9700
C12—O3	1.405 (3)	C25—H25B	0.9700
C12—H12A	0.9700	C26—N6	1.486 (3)
C12—H12B	0.9700	C26—H26A	0.9700
C13—O3	1.423 (3)	C26—H26B	0.9700
C13—C14	1.484 (4)	O1—S1	1.4472 (14)
C13—H13A	0.9700	O2—S1	1.4375 (14)
C13—H13B	0.9700	S1—N1	1.6023 (14)
C14—N4	1.459 (2)	N6—H6A	0.8900
C14—H14A	0.9700	N6—H6B	0.8900

C2—C1—C6	120.69 (18)	C17—C18—H18	119.5
C2—C1—S1	120.00 (15)	C19—C18—H18	119.5
C6—C1—S1	119.20 (14)	C20—C19—C18	118.13 (18)
C1—C2—C3	118.5 (2)	C20—C19—C22	121.3 (2)
C1—C2—H2	120.8	C18—C19—C22	120.6 (2)
C3—C2—H2	120.8	C19—C20—C21	121.3 (2)
C4—C3—C2	120.9 (2)	C19—C20—H20	119.3
C4—C3—H3	119.5	C21—C20—H20	119.3
C2—C3—H3	119.5	C20—C21—C16	120.01 (19)
C3—C4—C5	120.1 (2)	C20—C21—H21	120.0
C3—C4—H4	120.0	C16—C21—H21	120.0
C5—C4—H4	120.0	C19—C22—H22A	109.5
C4—C5—C6	120.1 (2)	C19—C22—H22B	109.5
C4—C5—H5	120.0	H22A—C22—H22B	109.5
C6—C5—H5	120.0	C19—C22—H22C	109.5
C5—C6—C1	119.8 (2)	H22A—C22—H22C	109.5
C5—C6—H6	120.1	H22B—C22—H22C	109.5
C1—C6—H6	120.1	O4—C23—C24	111.16 (18)
N3—C7—N1	121.60 (15)	O4—C23—H23A	109.4
N3—C7—N2	124.35 (16)	C24—C23—H23A	109.4
N1—C7—N2	114.01 (15)	O4—C23—H23B	109.4
N3—C8—N4	115.94 (15)	C24—C23—H23B	109.4
N3—C8—C9	119.96 (15)	H23A—C23—H23B	108.0
N4—C8—C9	124.00 (16)	N6—C24—C23	109.7 (2)
C10—C9—C15	118.84 (15)	N6—C24—H24A	109.7
C10—C9—C8	116.65 (15)	C23—C24—H24A	109.7
C15—C9—C8	123.66 (16)	N6—C24—H24B	109.7
N2—C10—C9	122.75 (15)	C23—C24—H24B	109.7
N2—C10—C16	116.35 (16)	H24A—C24—H24B	108.2
C9—C10—C16	120.89 (16)	O4—C25—C26	111.5 (2)
N4—C11—C12	108.46 (17)	O4—C25—H25A	109.3
N4—C11—H11A	110.0	C26—C25—H25A	109.3
C12—C11—H11A	110.0	O4—C25—H25B	109.3
N4—C11—H11B	110.0	C26—C25—H25B	109.3
C12—C11—H11B	110.0	H25A—C25—H25B	108.0
H11A—C11—H11B	108.4	N6—C26—C25	109.50 (18)
O3—C12—C11	112.4 (2)	N6—C26—H26A	109.8
O3—C12—H12A	109.1	C25—C26—H26A	109.8
C11—C12—H12A	109.1	N6—C26—H26B	109.8
O3—C12—H12B	109.1	C25—C26—H26B	109.8
C11—C12—H12B	109.1	H26A—C26—H26B	108.2
H12A—C12—H12B	107.9	C12—O3—C13	110.05 (19)
O3—C13—C14	112.2 (2)	C25—O4—C23	109.80 (17)
O3—C13—H13A	109.2	O2—S1—O1	115.69 (9)
C14—C13—H13A	109.2	O2—S1—N1	114.60 (8)
O3—C13—H13B	109.2	O1—S1—N1	103.82 (8)
C14—C13—H13B	109.2	O2—S1—C1	107.62 (9)
H13A—C13—H13B	107.9	O1—S1—C1	106.78 (8)
N4—C14—C13	109.8 (2)	N1—S1—C1	107.86 (8)
N4—C14—H14A	109.7	C7—N1—S1	119.59 (12)
C13—C14—H14A	109.7	C10—N2—C7	116.83 (15)
N4—C14—H14B	109.7	C8—N3—C7	119.39 (15)
C13—C14—H14B	109.7	C8—N4—C14	125.78 (15)
H14A—C14—H14B	108.2	C8—N4—C11	119.25 (15)
N5—C15—C9	177.6 (2)	C14—N4—C11	111.35 (15)
C17—C16—C21	118.84 (16)	C26—N6—C24	110.01 (16)
C17—C16—C10	121.61 (16)	C26—N6—H6A	109.7
C21—C16—C10	119.55 (16)	C24—N6—H6A	109.7
C18—C17—C16	120.40 (19)	C26—N6—H6B	109.7
C18—C17—H17	119.8	C24—N6—H6B	109.7
C16—C17—H17	119.8	H6A—N6—H6B	108.2
C17—C18—C19	121.1 (2)

C7—N1—S1—C1	63.74 (15)	N3—C7—N1—S1	1.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···O1ⁱ	0.89	2.45	3.113 (2)	131
N6—H6A···N1ⁱ	0.89	2.19	3.059 (2)	165
N6—H6B···N2	0.89	1.95	2.831 (2)	171

Symmetry code: (i) −x+1, −y+1, −z+1.

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