Crystal structure and anti­diabetic activity of 2-amino­spiro­pyrazolinium tosyl­ates and the product of O-tosyl­ation of β-(benzimidazol-1-yl)propio­amidoxime

2-Amino-1,5-di­aza­spiro­[4.5]dec-1-en-5-ium salts possess bioactivity tuned by the nature of the heteroatoms in the six-membered ring and the counter-ion. The mol­ecular environment of these cations in solids provides an opportunity to establish the conformations and hydro­gen-bonding patterns typical for this family. β-Amino­propio­amidoxime tosyl­ation products [2-amino-1,5-di­aza­spiro­[4.5]dec-1-en-5-ium tosyl­ates and the product of the O-tosyl­ation of β-(benzimidazol-1-yl)propio­amidoxime, namely, 2-amino-1,5-di­aza­spiro­[4.5]dec-1-en-5-ium tosyl­ate, C₈H₁₆N₃⁺·C₇H₇O₃S⁻ (6), 2-amino-8-oxa-1,5-di­aza­spiro­[4.5]dec-1-en-5-ium tosyl­ate, C₇H₁₄N₃O⁺·C₇H₇O₃S⁻ (7), the monohydrate of 7, C₇H₁₄N₃O⁺·C₇H₇O₃S⁻·H₂O (7a), 2-amino-8-thia-1,5-di­aza­spiro­[4.5]dec-1-en-5-ium tosyl­ate, C₇H₁₄N₃S⁺·C₇H₇O₃S⁻ (8), 2-amino-8-phenyl-1,5,8-tri­aza­spiro­[4.5]dec-1-en-5-ium tosyl­ate, C₁₃H₁₉N₄⁺·C₇H₇O₃S⁻ (9), and 3-(1H-benzimidazol-1-yl)-N′-(tos­yloxy)propanimidamide, C₁₇H₁₈N₄O₃S (10)] were investigated using X-ray diffraction to study peculiarities of their mol­ecular geometry and inter­molecular inter­actions. In vitro anti­tubercular and anti­diabetic screening of the β-am­ino­propio­amidoxime tosyl­ation products was also carried out. It was revealed that this series of com­pounds does not have activity against drug-sensitive and multidrug-resistant M. tuberculosis strains, and exhibits high and moderate anti­diabetic α-amylase and α-glucosidase activity. Using the hydro­gen-bond propensity tool, we found that the inclination of counter-ions and atoms to act as acceptors of hydro­gen bonds for the amino group decreases passing from tosyl­ate O atoms to water mol­ecules and the N atoms of five-membered rings. This fact is probably the reason for the formation in the solids of hydro­gen-bonded tetra­mers consisting of two anions and two cations, and the rare occurrence of 2-amino­spiro­pyrazolinium salt hydrates.

Computing details

For all structures, data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

2-Amino-1,5-diazaspiro[4.5]dec-1-en-5-ium 4-methylbenzenesulfonate (6)

Crystal data

C8H16N3^+·C7H7O3S^−	F(000) = 696
Mr = 325.42	Dx = 1.382 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.1202 (3) Å	Cell parameters from 8847 reflections
b = 25.213 (1) Å	θ = 2.6–37.7°
c = 10.5669 (4) Å	µ = 0.22 mm^−1
β = 106.403 (2)°	T = 100 K
V = 1564.20 (12) Å^3	Plate, colourless
Z = 4	0.33 × 0.19 × 0.05 mm

Data collection

Bruker D8 Quest PHOTON CCD detector diffractometer	6080 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.081
ω scans	θmax = 37.9°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −10→10
Tmin = 0.590, Tmax = 0.747	k = −42→43
39454 measured reflections	l = −17→18
8355 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.049	H-atom parameters constrained
wR(F^2) = 0.129	w = 1/[σ^2(Fo^2) + (0.0527P)^2 + 0.4847P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.003
8355 reflections	Δρmax = 0.57 e Å^−3
200 parameters	Δρmin = −0.58 e Å^−3
0 restraints

Special details

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. Single crystals were obtained from reaction mixtures. The intensities of reflections for the samples were measured with a Bruker Quest diffractometer using MoK_? radiation with multilayer optics (? = 0.71073Å)at 100.0 (2) (6, 7, 7·H₂O, 9, 10) or 295.0 (2) K (8a). The structures were solved by the direct method and refined by full-matrix least squares against F². Non-hydrogen atoms were refined anisotropically.

All calculations were made using the SHELXL ??(Sheldrick, 2015a)? and OLEX2 ??(Dolomanov et al., 2009)?] program packages. Experimental details and crystal parameters are listed in Table 1.

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

	x	y	z	Uiso*/Ueq
S1	0.54703 (4)	0.61026 (2)	0.54442 (3)	0.01154 (6)
O1	0.60040 (16)	0.56781 (3)	0.46451 (9)	0.01973 (17)
O2	0.30391 (14)	0.61544 (3)	0.52904 (9)	0.01677 (15)
O3	0.68106 (15)	0.60728 (3)	0.68277 (8)	0.01814 (16)
C9	0.62948 (17)	0.66972 (4)	0.48035 (10)	0.01138 (16)
C10	0.85793 (18)	0.68393 (4)	0.51429 (11)	0.01447 (18)
H10	0.968608	0.662672	0.573953	0.017*
C11	0.92371 (19)	0.72948 (5)	0.46040 (11)	0.01600 (19)
H11	1.079648	0.739539	0.485620	0.019*
C12	0.7655 (2)	0.76070 (4)	0.37010 (11)	0.01529 (19)
C13	0.53625 (19)	0.74570 (4)	0.33644 (11)	0.01629 (19)
H13	0.425655	0.766489	0.275387	0.020*
C14	0.46835 (18)	0.70059 (4)	0.39148 (11)	0.01473 (18)
H14	0.312043	0.690897	0.368354	0.018*
C15	0.8412 (2)	0.80853 (5)	0.30823 (13)	0.0243 (3)
H15A	0.985575	0.821692	0.366206	0.036*
H15B	0.725248	0.836369	0.295539	0.036*
H15C	0.862036	0.798670	0.222681	0.036*
N1	0.97057 (15)	0.55048 (3)	0.20392 (8)	0.01080 (14)
N2	0.77566 (15)	0.52136 (4)	0.11896 (8)	0.01160 (15)
N3	0.54622 (16)	0.45251 (4)	0.14997 (9)	0.01406 (16)
H3A	0.459498	0.455162	0.068154	0.017*
H3B	0.515894	0.428443	0.202917	0.017*
C1	0.72355 (17)	0.48497 (4)	0.19371 (10)	0.01120 (16)
C2	0.87632 (18)	0.48223 (4)	0.33227 (10)	0.01319 (17)
H2A	0.919098	0.445227	0.359661	0.016*
H2B	0.805188	0.498907	0.395689	0.016*
C3	1.07882 (18)	0.51394 (4)	0.31840 (10)	0.01422 (18)
H3C	1.150452	0.534303	0.399633	0.017*
H3D	1.194512	0.490660	0.297816	0.017*
C4	0.88652 (18)	0.60060 (4)	0.25419 (10)	0.01297 (17)
H4A	1.015389	0.618103	0.318934	0.016*
H4B	0.771142	0.591209	0.299868	0.016*
C5	0.7827 (2)	0.63885 (4)	0.14264 (12)	0.0171 (2)
H5A	0.733354	0.671460	0.179011	0.021*
H5B	0.646660	0.622417	0.081279	0.021*
C6	0.9545 (2)	0.65332 (5)	0.06738 (12)	0.0193 (2)
H6A	0.880513	0.676399	−0.008399	0.023*
H6B	1.083192	0.673146	0.126156	0.023*
C7	1.0432 (2)	0.60317 (5)	0.01797 (11)	0.0175 (2)
H7A	0.917739	0.586222	−0.050324	0.021*
H7B	1.164122	0.612852	−0.023344	0.021*
C8	1.13819 (18)	0.56387 (5)	0.12854 (11)	0.01450 (18)
H8A	1.181973	0.530931	0.090900	0.017*
H8B	1.277315	0.578954	0.190121	0.017*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01160 (10)	0.01244 (11)	0.01105 (10)	0.00005 (8)	0.00394 (8)	0.00045 (8)
O1	0.0273 (4)	0.0134 (4)	0.0232 (4)	−0.0005 (3)	0.0148 (4)	−0.0023 (3)
O2	0.0115 (3)	0.0191 (4)	0.0204 (4)	−0.0018 (3)	0.0057 (3)	0.0009 (3)
O3	0.0184 (4)	0.0218 (4)	0.0123 (3)	−0.0007 (3)	0.0011 (3)	0.0046 (3)
C9	0.0114 (4)	0.0119 (4)	0.0106 (4)	−0.0004 (3)	0.0027 (3)	−0.0006 (3)
C10	0.0118 (4)	0.0152 (4)	0.0150 (4)	0.0001 (3)	0.0015 (3)	0.0005 (4)
C11	0.0135 (4)	0.0172 (5)	0.0169 (5)	−0.0037 (3)	0.0035 (3)	−0.0011 (4)
C12	0.0193 (5)	0.0138 (4)	0.0126 (4)	−0.0030 (4)	0.0043 (4)	−0.0004 (3)
C13	0.0173 (5)	0.0159 (4)	0.0141 (4)	0.0008 (4)	0.0018 (4)	0.0030 (4)
C14	0.0117 (4)	0.0172 (5)	0.0142 (4)	0.0007 (3)	0.0018 (3)	0.0021 (4)
C15	0.0309 (6)	0.0202 (5)	0.0199 (5)	−0.0095 (5)	0.0041 (5)	0.0035 (4)
N1	0.0107 (3)	0.0126 (4)	0.0082 (3)	0.0002 (3)	0.0011 (3)	0.0001 (3)
N2	0.0111 (3)	0.0139 (4)	0.0082 (3)	−0.0013 (3)	0.0000 (3)	−0.0011 (3)
N3	0.0154 (4)	0.0149 (4)	0.0103 (4)	−0.0029 (3)	0.0012 (3)	0.0014 (3)
C1	0.0123 (4)	0.0121 (4)	0.0088 (4)	0.0016 (3)	0.0024 (3)	−0.0002 (3)
C2	0.0153 (4)	0.0143 (4)	0.0082 (4)	−0.0001 (3)	0.0004 (3)	0.0017 (3)
C3	0.0139 (4)	0.0152 (4)	0.0107 (4)	0.0007 (3)	−0.0012 (3)	0.0026 (3)
C4	0.0155 (4)	0.0124 (4)	0.0113 (4)	0.0001 (3)	0.0042 (3)	−0.0018 (3)
C5	0.0190 (5)	0.0144 (4)	0.0174 (5)	0.0029 (4)	0.0045 (4)	0.0029 (4)
C6	0.0201 (5)	0.0182 (5)	0.0190 (5)	−0.0013 (4)	0.0048 (4)	0.0060 (4)
C7	0.0166 (5)	0.0243 (5)	0.0126 (4)	−0.0022 (4)	0.0056 (4)	0.0029 (4)
C8	0.0115 (4)	0.0196 (5)	0.0132 (4)	−0.0001 (3)	0.0047 (3)	0.0005 (4)

Geometric parameters (Å, º)

S1—O1	1.4563 (9)	N3—H3A	0.8800
S1—O2	1.4564 (9)	N3—H3B	0.8800
S1—O3	1.4624 (9)	N3—C1	1.3334 (13)
S1—C9	1.7758 (11)	C1—C2	1.4998 (14)
C9—C10	1.3887 (14)	C2—H2A	0.9900
C9—C14	1.3917 (14)	C2—H2B	0.9900
C10—H10	0.9500	C2—C3	1.5163 (15)
C10—C11	1.3909 (16)	C3—H3C	0.9900
C11—H11	0.9500	C3—H3D	0.9900
C11—C12	1.3949 (16)	C4—H4A	0.9900
C12—C13	1.3987 (16)	C4—H4B	0.9900
C12—C15	1.5059 (16)	C4—C5	1.5168 (15)
C13—H13	0.9500	C5—H5A	0.9900
C13—C14	1.3932 (16)	C5—H5B	0.9900
C14—H14	0.9500	C5—C6	1.5308 (17)
C15—H15A	0.9800	C6—H6A	0.9900
C15—H15B	0.9800	C6—H6B	0.9900
C15—H15C	0.9800	C6—C7	1.5254 (18)
N1—N2	1.4708 (12)	C7—H7A	0.9900
N1—C3	1.5160 (13)	C7—H7B	0.9900
N1—C4	1.5160 (13)	C7—C8	1.5169 (16)
N1—C8	1.5041 (14)	C8—H8A	0.9900
N2—C1	1.3075 (14)	C8—H8B	0.9900
O1—S1—O2	112.99 (5)	C1—C2—H2A	111.7
O1—S1—O3	112.80 (5)	C1—C2—H2B	111.7
O1—S1—C9	105.37 (5)	C1—C2—C3	100.52 (8)
O2—S1—O3	112.52 (5)	H2A—C2—H2B	109.4
O2—S1—C9	105.85 (5)	C3—C2—H2A	111.7
O3—S1—C9	106.55 (5)	C3—C2—H2B	111.7
C10—C9—S1	119.55 (8)	N1—C3—C2	102.27 (8)
C10—C9—C14	119.99 (10)	N1—C3—H3C	111.3
C14—C9—S1	120.38 (8)	N1—C3—H3D	111.3
C9—C10—H10	120.2	C2—C3—H3C	111.3
C9—C10—C11	119.60 (10)	C2—C3—H3D	111.3
C11—C10—H10	120.2	H3C—C3—H3D	109.2
C10—C11—H11	119.3	N1—C4—H4A	109.3
C10—C11—C12	121.38 (10)	N1—C4—H4B	109.3
C12—C11—H11	119.3	N1—C4—C5	111.53 (9)
C11—C12—C13	118.30 (10)	H4A—C4—H4B	108.0
C11—C12—C15	120.64 (11)	C5—C4—H4A	109.3
C13—C12—C15	121.04 (11)	C5—C4—H4B	109.3
C12—C13—H13	119.6	C4—C5—H5A	109.5
C14—C13—C12	120.70 (10)	C4—C5—H5B	109.5
C14—C13—H13	119.6	C4—C5—C6	110.89 (9)
C9—C14—C13	120.01 (10)	H5A—C5—H5B	108.0
C9—C14—H14	120.0	C6—C5—H5A	109.5
C13—C14—H14	120.0	C6—C5—H5B	109.5
C12—C15—H15A	109.5	C5—C6—H6A	109.6
C12—C15—H15B	109.5	C5—C6—H6B	109.6
C12—C15—H15C	109.5	H6A—C6—H6B	108.2
H15A—C15—H15B	109.5	C7—C6—C5	110.10 (9)
H15A—C15—H15C	109.5	C7—C6—H6A	109.6
H15B—C15—H15C	109.5	C7—C6—H6B	109.6
N2—N1—C3	106.26 (8)	C6—C7—H7A	109.2
N2—N1—C4	109.46 (8)	C6—C7—H7B	109.2
N2—N1—C8	110.23 (8)	H7A—C7—H7B	107.9
C4—N1—C3	110.00 (8)	C8—C7—C6	111.95 (9)
C8—N1—C3	110.44 (8)	C8—C7—H7A	109.2
C8—N1—C4	110.37 (8)	C8—C7—H7B	109.2
C1—N2—N1	106.00 (8)	N1—C8—C7	112.60 (9)
H3A—N3—H3B	120.0	N1—C8—H8A	109.1
C1—N3—H3A	120.0	N1—C8—H8B	109.1
C1—N3—H3B	120.0	C7—C8—H8A	109.1
N2—C1—N3	122.33 (9)	C7—C8—H8B	109.1
N2—C1—C2	115.52 (9)	H8A—C8—H8B	107.8
N3—C1—C2	122.15 (9)
S1—C9—C10—C11	177.67 (8)	N2—N1—C3—C2	−30.54 (10)
S1—C9—C14—C13	−176.66 (9)	N2—N1—C4—C5	−65.13 (11)
O1—S1—C9—C10	−78.61 (10)	N2—N1—C8—C7	66.51 (11)
O1—S1—C9—C14	98.15 (10)	N2—C1—C2—C3	−16.10 (12)
O2—S1—C9—C10	161.44 (9)	N3—C1—C2—C3	164.06 (10)
O2—S1—C9—C14	−21.79 (10)	C1—C2—C3—N1	26.84 (10)
O3—S1—C9—C10	41.46 (10)	C3—N1—N2—C1	21.35 (10)
O3—S1—C9—C14	−141.78 (9)	C3—N1—C4—C5	178.47 (9)
C9—C10—C11—C12	−1.59 (17)	C3—N1—C8—C7	−176.37 (9)
C10—C9—C14—C13	0.09 (16)	C4—N1—N2—C1	−97.39 (9)
C10—C11—C12—C13	1.26 (17)	C4—N1—C3—C2	87.84 (9)
C10—C11—C12—C15	−177.29 (11)	C4—N1—C8—C7	−54.52 (11)
C11—C12—C13—C14	−0.25 (17)	C4—C5—C6—C7	55.63 (13)
C12—C13—C14—C9	−0.41 (17)	C5—C6—C7—C8	−53.82 (13)
C14—C9—C10—C11	0.89 (16)	C6—C7—C8—N1	54.20 (12)
C15—C12—C13—C14	178.29 (11)	C8—N1—N2—C1	141.04 (9)
N1—N2—C1—N3	176.82 (9)	C8—N1—C3—C2	−150.09 (9)
N1—N2—C1—C2	−3.02 (12)	C8—N1—C4—C5	56.35 (11)
N1—C4—C5—C6	−57.64 (12)

2-Amino-8-oxa-1,5-diazaspiro[4.5]dec-1-en-5-ium 4-methylbenzenesulfonate (7)

Crystal data

C7H14N3O^+·C7H7O3S^−	Z = 4
Mr = 327.40	F(000) = 696
Triclinic, P1	Dx = 1.360 Mg m^−3
a = 8.504 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.229 (5) Å	Cell parameters from 1568 reflections
c = 15.834 (6) Å	θ = 2.6–25.8°
α = 102.194 (8)°	µ = 0.22 mm^−1
β = 91.589 (7)°	T = 120 K
γ = 95.875 (8)°	Prism, colourless
V = 1598.9 (11) Å^3	0.46 × 0.21 × 0.17 mm

Data collection

Bruker APEXII CCD area detector diffractometer	4280 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.139
phi and ω scans	θmax = 32.9°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −12→12
Tmin = 0.624, Tmax = 0.747	k = −18→18
25066 measured reflections	l = −24→24
11813 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.085	H-atom parameters constrained
wR(F^2) = 0.153	w = 1/[σ^2(Fo^2) + (0.010P)^2 + 1.P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.005
11813 reflections	Δρmax = 0.53 e Å^−3
399 parameters	Δρmin = −0.79 e Å^−3
0 restraints

Special details

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. Single crystals were obtained from reaction mixtures. The intensities of reflections for the samples were measured with a Bruker Quest diffractometer using MoK_? radiation with multilayer optics (? = 0.71073Å)at 100.0 (2) (6, 7, 7·H₂O, 9, 10) or 295.0 (2) K (8a). The structures were solved by the direct method and refined by full-matrix least squares against F². Non-hydrogen atoms were refined anisotropically.

All calculations were made using the SHELXL ??(Sheldrick, 2015a)? and OLEX2 ??(Dolomanov et al., 2009)?] program packages. Experimental details and crystal parameters are listed in Table 1.

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

	x	y	z	Uiso*/Ueq
S1	0.79797 (10)	0.22385 (8)	0.33622 (6)	0.0196 (2)
O1	0.7587 (3)	0.3252 (2)	0.39487 (15)	0.0266 (6)
O2	0.9663 (3)	0.2094 (2)	0.34222 (16)	0.0257 (6)
O3	0.6960 (3)	0.1233 (2)	0.34444 (16)	0.0292 (6)
C8	0.7628 (4)	0.2443 (3)	0.2302 (2)	0.0191 (8)
C9	0.8279 (4)	0.1778 (3)	0.1604 (2)	0.0254 (8)
H9	0.8894	0.1205	0.1699	0.030*
C10	0.8043 (4)	0.1938 (3)	0.0775 (2)	0.0286 (9)
H10	0.8496	0.1476	0.0306	0.034*
C11	0.7126 (4)	0.2791 (3)	0.0617 (2)	0.0281 (9)
C12	0.6487 (4)	0.3443 (3)	0.1323 (2)	0.0274 (9)
H12	0.5873	0.4019	0.1233	0.033*
C13	0.6719 (4)	0.3278 (3)	0.2159 (2)	0.0233 (8)
H13	0.6260	0.3733	0.2629	0.028*
C14	0.6896 (5)	0.2974 (4)	−0.0289 (3)	0.0427 (11)
H14A	0.7924	0.3202	−0.0502	0.064*
H14B	0.6200	0.3566	−0.0285	0.064*
H14C	0.6414	0.2273	−0.0669	0.064*
S2	0.78528 (10)	0.69893 (8)	0.34257 (6)	0.0200 (2)
O5	0.9205 (3)	0.7715 (2)	0.38819 (16)	0.0283 (6)
O6	0.6389 (3)	0.7205 (2)	0.38747 (16)	0.0283 (6)
O7	0.8072 (3)	0.58065 (19)	0.32151 (16)	0.0271 (6)
C22	0.7604 (4)	0.7391 (3)	0.2423 (2)	0.0199 (8)
C23	0.7928 (4)	0.6686 (3)	0.1650 (2)	0.0268 (9)
H23	0.8252	0.5967	0.1658	0.032*
C24	0.7783 (5)	0.7018 (3)	0.0867 (2)	0.0311 (9)
H24	0.7983	0.6517	0.0345	0.037*
C25	0.7345 (4)	0.8083 (3)	0.0840 (2)	0.0287 (9)
C26	0.7018 (4)	0.8775 (3)	0.1613 (2)	0.0259 (8)
H26	0.6713	0.9499	0.1605	0.031*
C27	0.7119 (4)	0.8452 (3)	0.2394 (2)	0.0225 (8)
H27	0.6863	0.8941	0.2910	0.027*
C28	0.7209 (5)	0.8466 (4)	−0.0006 (3)	0.0442 (12)
H28A	0.8251	0.8510	−0.0254	0.066*
H28B	0.6825	0.9209	0.0100	0.066*
H28C	0.6465	0.7926	−0.0410	0.066*
O4	0.2048 (3)	−0.0119 (2)	0.15674 (16)	0.0336 (7)
N1	0.2362 (3)	0.0223 (2)	0.34354 (19)	0.0199 (6)
N2	0.3508 (3)	−0.0574 (2)	0.35762 (19)	0.0217 (7)
N3	0.4101 (3)	−0.1404 (2)	0.47208 (19)	0.0225 (7)
H3A	0.4798	−0.1791	0.4424	0.027*
H3B	0.3927	−0.1472	0.5254	0.027*
C1	0.1901 (4)	0.0799 (3)	0.4326 (2)	0.0225 (8)
H1A	0.2626	0.1489	0.4564	0.027*
H1B	0.0801	0.0997	0.4310	0.027*
C2	0.2059 (4)	−0.0091 (3)	0.4848 (2)	0.0222 (8)
H2A	0.2416	0.0247	0.5456	0.027*
H2B	0.1054	−0.0582	0.4834	0.027*
C3	0.3310 (4)	−0.0717 (3)	0.4364 (2)	0.0189 (7)
C4	0.0935 (4)	−0.0433 (3)	0.2907 (2)	0.0234 (8)
H4A	0.0487	−0.1031	0.3194	0.028*
H4B	0.0113	0.0075	0.2869	0.028*
C5	0.1388 (4)	−0.0955 (3)	0.2011 (2)	0.0288 (9)
H5A	0.2172	−0.1490	0.2051	0.035*
H5B	0.0440	−0.1383	0.1674	0.035*
C6	0.3462 (4)	0.0471 (3)	0.2047 (2)	0.0321 (10)
H6A	0.3936	0.1039	0.1738	0.038*
H6B	0.4241	−0.0070	0.2076	0.038*
C7	0.3129 (4)	0.1049 (3)	0.2950 (2)	0.0254 (8)
H7A	0.2422	0.1637	0.2923	0.031*
H7B	0.4132	0.1420	0.3261	0.031*
O8	1.2450 (3)	0.5115 (2)	0.15116 (17)	0.0364 (7)
N4	1.2217 (3)	0.5049 (2)	0.33160 (19)	0.0225 (7)
N5	1.3625 (3)	0.4490 (3)	0.34784 (19)	0.0224 (7)
N6	1.4441 (3)	0.3608 (2)	0.45482 (19)	0.0243 (7)
H6C	1.5313	0.3447	0.4285	0.029*
H6D	1.4249	0.3403	0.5039	0.029*
C15	1.1372 (4)	0.5285 (4)	0.4154 (2)	0.0312 (9)
H15A	1.0209	0.5183	0.4043	0.037*
H15B	1.1697	0.6060	0.4488	0.037*
C16	1.1897 (4)	0.4418 (3)	0.4631 (2)	0.0229 (8)
H16A	1.2083	0.4736	0.5259	0.027*
H16B	1.1115	0.3741	0.4540	0.027*
C17	1.3410 (4)	0.4163 (3)	0.4203 (2)	0.0207 (8)
C18	1.1156 (4)	0.4280 (3)	0.2608 (2)	0.0253 (8)
H18A	1.0869	0.3551	0.2774	0.030*
H18B	1.0169	0.4622	0.2535	0.030*
C19	1.1977 (5)	0.4083 (3)	0.1766 (2)	0.0330 (10)
H19A	1.2920	0.3690	0.1829	0.040*
H19B	1.1252	0.3592	0.1309	0.040*
C20	1.3494 (5)	0.5831 (3)	0.2164 (3)	0.0351 (10)
H20A	1.3825	0.6539	0.1976	0.042*
H20B	1.4454	0.5458	0.2235	0.042*
C21	1.2743 (4)	0.6103 (3)	0.3014 (3)	0.0295 (9)
H21A	1.1821	0.6519	0.2956	0.035*
H21B	1.3512	0.6593	0.3449	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0119 (4)	0.0234 (5)	0.0244 (5)	0.0056 (4)	0.0005 (4)	0.0052 (4)
O1	0.0302 (15)	0.0276 (14)	0.0214 (14)	0.0156 (11)	0.0010 (11)	−0.0021 (11)
O2	0.0106 (12)	0.0354 (15)	0.0334 (15)	0.0092 (11)	0.0001 (10)	0.0098 (12)
O3	0.0240 (14)	0.0279 (15)	0.0367 (16)	−0.0071 (11)	−0.0014 (12)	0.0145 (13)
C8	0.0121 (17)	0.0227 (19)	0.0219 (19)	0.0012 (14)	−0.0004 (14)	0.0037 (15)
C9	0.0194 (19)	0.030 (2)	0.029 (2)	0.0094 (16)	0.0030 (16)	0.0076 (17)
C10	0.026 (2)	0.032 (2)	0.026 (2)	0.0106 (17)	0.0040 (17)	−0.0001 (18)
C11	0.024 (2)	0.034 (2)	0.027 (2)	0.0040 (17)	−0.0007 (17)	0.0087 (18)
C12	0.025 (2)	0.033 (2)	0.027 (2)	0.0135 (17)	0.0002 (16)	0.0092 (18)
C13	0.0198 (19)	0.029 (2)	0.0220 (19)	0.0074 (16)	−0.0006 (15)	0.0050 (16)
C14	0.048 (3)	0.055 (3)	0.029 (2)	0.012 (2)	0.001 (2)	0.015 (2)
S2	0.0133 (4)	0.0232 (5)	0.0247 (5)	0.0067 (4)	0.0015 (4)	0.0058 (4)
O5	0.0233 (14)	0.0319 (15)	0.0286 (14)	−0.0032 (12)	−0.0066 (11)	0.0084 (12)
O6	0.0175 (13)	0.0377 (16)	0.0359 (16)	0.0155 (11)	0.0132 (11)	0.0142 (13)
O7	0.0325 (15)	0.0173 (13)	0.0334 (15)	0.0130 (11)	−0.0013 (12)	0.0053 (12)
C22	0.0145 (17)	0.0232 (19)	0.0212 (19)	0.0034 (14)	−0.0012 (14)	0.0024 (16)
C23	0.026 (2)	0.026 (2)	0.029 (2)	0.0100 (16)	0.0024 (17)	0.0045 (17)
C24	0.036 (2)	0.035 (2)	0.022 (2)	0.0078 (19)	0.0037 (17)	0.0016 (18)
C25	0.025 (2)	0.038 (2)	0.024 (2)	−0.0023 (18)	−0.0050 (16)	0.0111 (18)
C26	0.0154 (18)	0.031 (2)	0.033 (2)	0.0054 (16)	−0.0011 (16)	0.0110 (18)
C27	0.0141 (18)	0.028 (2)	0.026 (2)	0.0058 (15)	0.0012 (15)	0.0063 (17)
C28	0.048 (3)	0.056 (3)	0.031 (2)	0.013 (2)	−0.004 (2)	0.012 (2)
O4	0.0319 (16)	0.0460 (18)	0.0241 (15)	0.0035 (14)	−0.0012 (12)	0.0108 (14)
N1	0.0111 (14)	0.0226 (16)	0.0276 (17)	0.0059 (12)	0.0002 (12)	0.0068 (13)
N2	0.0113 (15)	0.0246 (16)	0.0306 (18)	0.0096 (12)	−0.0016 (13)	0.0059 (14)
N3	0.0181 (16)	0.0261 (17)	0.0259 (17)	0.0121 (13)	0.0021 (13)	0.0066 (14)
C1	0.0141 (17)	0.027 (2)	0.026 (2)	0.0089 (15)	0.0013 (14)	0.0020 (16)
C2	0.0166 (18)	0.027 (2)	0.025 (2)	0.0099 (15)	0.0030 (15)	0.0062 (16)
C3	0.0099 (16)	0.0229 (19)	0.0246 (19)	0.0035 (14)	0.0016 (14)	0.0058 (16)
C4	0.0138 (18)	0.028 (2)	0.029 (2)	0.0033 (15)	−0.0021 (15)	0.0063 (17)
C5	0.025 (2)	0.034 (2)	0.027 (2)	0.0059 (17)	−0.0034 (17)	0.0066 (18)
C6	0.023 (2)	0.045 (3)	0.031 (2)	0.0053 (18)	0.0044 (17)	0.014 (2)
C7	0.0161 (18)	0.028 (2)	0.037 (2)	0.0046 (15)	−0.0021 (16)	0.0173 (18)
O8	0.0409 (18)	0.0415 (18)	0.0281 (16)	−0.0020 (14)	−0.0009 (13)	0.0136 (14)
N4	0.0173 (16)	0.0285 (18)	0.0232 (17)	0.0080 (13)	−0.0010 (13)	0.0067 (14)
N5	0.0153 (15)	0.0309 (18)	0.0243 (17)	0.0097 (13)	−0.0002 (12)	0.0103 (14)
N6	0.0185 (16)	0.0323 (18)	0.0270 (17)	0.0118 (13)	0.0025 (13)	0.0126 (14)
C15	0.024 (2)	0.048 (3)	0.023 (2)	0.0197 (18)	0.0034 (16)	0.0036 (19)
C16	0.0140 (17)	0.031 (2)	0.023 (2)	0.0044 (15)	0.0018 (15)	0.0039 (17)
C17	0.0160 (18)	0.026 (2)	0.0203 (19)	0.0034 (15)	−0.0008 (14)	0.0046 (16)
C18	0.0179 (19)	0.032 (2)	0.025 (2)	0.0028 (16)	−0.0041 (15)	0.0055 (17)
C19	0.032 (2)	0.034 (2)	0.030 (2)	0.0014 (18)	−0.0007 (18)	0.0019 (19)
C20	0.033 (2)	0.036 (2)	0.038 (2)	−0.0005 (19)	−0.002 (2)	0.014 (2)
C21	0.024 (2)	0.023 (2)	0.041 (2)	0.0027 (16)	−0.0075 (18)	0.0088 (18)

Geometric parameters (Å, º)

S1—O1	1.458 (2)	O4—C6	1.444 (4)
S1—O2	1.463 (2)	N1—N2	1.491 (4)
S1—O3	1.462 (2)	N1—C1	1.519 (4)
S1—C8	1.770 (4)	N1—C4	1.509 (4)
C8—C9	1.392 (5)	N1—C7	1.502 (4)
C8—C13	1.393 (5)	N2—C3	1.309 (4)
C9—C10	1.379 (5)	N3—C3	1.332 (4)
C10—C11	1.422 (5)	C1—C2	1.513 (5)
C11—C12	1.388 (5)	C2—C3	1.506 (4)
C11—C14	1.509 (5)	C4—C5	1.506 (5)
C12—C13	1.392 (5)	C6—C7	1.503 (5)
S2—O5	1.451 (2)	O8—C19	1.427 (4)
S2—O6	1.470 (2)	O8—C20	1.425 (4)
S2—O7	1.447 (2)	N4—N5	1.481 (4)
S2—C22	1.772 (4)	N4—C15	1.515 (4)
C22—C23	1.392 (5)	N4—C18	1.510 (4)
C22—C27	1.410 (5)	N4—C21	1.499 (4)
C23—C24	1.389 (5)	N5—C17	1.305 (4)
C24—C25	1.399 (5)	N6—C17	1.334 (4)
C25—C26	1.387 (5)	C15—C16	1.519 (5)
C25—C28	1.514 (5)	C16—C17	1.501 (5)
C26—C27	1.378 (5)	C18—C19	1.508 (5)
O4—C5	1.436 (4)	C20—C21	1.494 (5)
O1—S1—O2	112.68 (15)	N2—N1—C1	106.5 (2)
O1—S1—O3	112.50 (16)	N2—N1—C4	109.0 (3)
O1—S1—C8	106.20 (16)	N2—N1—C7	109.4 (2)
O2—S1—C8	105.08 (15)	C4—N1—C1	110.8 (3)
O3—S1—O2	112.55 (15)	C7—N1—C1	112.0 (3)
O3—S1—C8	107.17 (15)	C7—N1—C4	109.1 (3)
C9—C8—S1	120.1 (3)	C3—N2—N1	105.4 (3)
C9—C8—C13	119.3 (3)	C2—C1—N1	102.5 (3)
C13—C8—S1	120.6 (3)	C3—C2—C1	100.3 (3)
C10—C9—C8	120.9 (3)	N2—C3—N3	123.3 (3)
C9—C10—C11	120.5 (3)	N2—C3—C2	115.9 (3)
C10—C11—C14	120.2 (3)	N3—C3—C2	120.7 (3)
C12—C11—C10	117.6 (3)	C5—C4—N1	110.4 (3)
C12—C11—C14	122.2 (4)	O4—C5—C4	111.7 (3)
C11—C12—C13	121.9 (3)	O4—C6—C7	112.1 (3)
C12—C13—C8	119.7 (3)	C6—C7—N1	111.0 (3)
O5—S2—O6	111.25 (16)	C20—O8—C19	109.9 (3)
O5—S2—C22	106.13 (16)	N5—N4—C15	107.2 (2)
O6—S2—C22	105.68 (15)	N5—N4—C18	109.4 (3)
O7—S2—O5	114.39 (15)	N5—N4—C21	109.0 (3)
O7—S2—O6	112.66 (15)	C18—N4—C15	110.7 (3)
O7—S2—C22	105.98 (16)	C21—N4—C15	112.3 (3)
C23—C22—S2	121.0 (3)	C21—N4—C18	108.2 (3)
C23—C22—C27	118.5 (3)	C17—N5—N4	106.1 (3)
C27—C22—S2	120.5 (3)	N4—C15—C16	103.4 (3)
C24—C23—C22	120.9 (3)	C17—C16—C15	100.8 (3)
C23—C24—C25	120.7 (4)	N5—C17—N6	123.0 (3)
C24—C25—C28	121.4 (4)	N5—C17—C16	116.3 (3)
C26—C25—C24	117.8 (3)	N6—C17—C16	120.7 (3)
C26—C25—C28	120.8 (4)	C19—C18—N4	110.6 (3)
C27—C26—C25	122.4 (4)	O8—C19—C18	111.6 (3)
C26—C27—C22	119.6 (3)	O8—C20—C21	112.3 (3)
C5—O4—C6	108.8 (3)	C20—C21—N4	110.6 (3)

2-Amino-8-oxa-1,5-diazaspiro[4.5]dec-1-en-5-ium 4-methylbenzenesulfonate monohydrate (7H2O)

Crystal data

C7H14N3O^+·C7H7O3S^−·H2O	F(000) = 736
Mr = 345.41	Dx = 1.365 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.2022 (5) Å	Cell parameters from 8385 reflections
b = 6.3857 (4) Å	θ = 2.5–35.4°
c = 34.166 (2) Å	µ = 0.22 mm^−1
β = 110.022 (1)°	T = 120 K
V = 1681.33 (18) Å^3	Prism, colourless
Z = 4	0.32 × 0.29 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer	6412 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.039
Absorption correction: multi-scan (SADABS; Bruker, 2014)	θmax = 36.3°, θmin = 2.5°
Tmin = 0.650, Tmax = 0.747	h = −13→13
29410 measured reflections	k = −10→10
7804 independent reflections	l = −55→56

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.101	w = 1/[σ^2(Fo^2) + (0.010P)^2 + 2.060P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.001
7804 reflections	Δρmax = 0.82 e Å^−3
209 parameters	Δρmin = −0.67 e Å^−3

Special details

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. Single crystals were obtained from reaction mixtures. The intensities of reflections for the samples were measured with a Bruker Quest diffractometer using MoK_? radiation with multilayer optics (? = 0.71073Å)at 100.0 (2) (6, 7, 7·H₂O, 9, 10) or 295.0 (2) K (8a). The structures were solved by the direct method and refined by full-matrix least squares against F². Non-hydrogen atoms were refined anisotropically.

All calculations were made using the SHELXL ??(Sheldrick, 2015a)? and OLEX2 ??(Dolomanov et al., 2009)?] program packages. Experimental details and crystal parameters are listed in Table 1.

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

	x	y	z	Uiso*/Ueq
S1	0.54052 (4)	0.27590 (4)	0.64645 (2)	0.01151 (5)
O1	0.40347 (12)	0.24998 (16)	0.66414 (3)	0.01916 (18)
O2	0.70196 (12)	0.17217 (15)	0.67146 (3)	0.01790 (18)
O3	0.56795 (13)	0.49421 (14)	0.63760 (3)	0.01957 (18)
C8	0.46781 (15)	0.14546 (18)	0.59766 (3)	0.01261 (19)
C9	0.33699 (17)	0.2352 (2)	0.56398 (4)	0.0197 (2)
H9	0.2921	0.3696	0.5666	0.024*
C10	0.27316 (18)	0.1253 (2)	0.52653 (4)	0.0223 (3)
H10	0.1862	0.1873	0.5034	0.027*
C11	0.33487 (18)	−0.0746 (2)	0.52240 (4)	0.0196 (2)
C12	0.46558 (19)	−0.1603 (2)	0.55637 (4)	0.0204 (2)
H12	0.5095	−0.2955	0.5540	0.024*
C13	0.53304 (17)	−0.05115 (19)	0.59384 (4)	0.0164 (2)
H13	0.6231	−0.1110	0.6166	0.020*
C14	0.2617 (2)	−0.1959 (3)	0.48220 (4)	0.0286 (3)
H14A	0.1351	−0.1816	0.4714	0.043*
H14B	0.2926	−0.3440	0.4874	0.043*
H14C	0.3098	−0.1406	0.4617	0.043*
O4	1.01656 (14)	0.10545 (19)	0.92155 (3)	0.0249 (2)
N1	0.86465 (12)	0.18465 (15)	0.83303 (3)	0.01179 (16)
N2	0.97895 (13)	0.34472 (16)	0.82508 (3)	0.01335 (17)
N3	0.94806 (14)	0.59263 (18)	0.77345 (3)	0.0183 (2)
H3A	1.0550	0.6374	0.7857	0.022*
H3B	0.8819	0.6507	0.7500	0.022*
C1	0.72237 (16)	0.1424 (2)	0.79172 (4)	0.0165 (2)
H1A	0.7571	0.0322	0.7758	0.020*
H1B	0.6130	0.1005	0.7957	0.020*
C2	0.70449 (15)	0.3533 (2)	0.77030 (4)	0.0163 (2)
H2A	0.6734	0.3384	0.7398	0.020*
H2B	0.6177	0.4431	0.7764	0.020*
C3	0.88626 (14)	0.43668 (19)	0.79034 (4)	0.01288 (19)
C4	0.78809 (15)	0.2677 (2)	0.86451 (4)	0.0155 (2)
H4A	0.7007	0.1677	0.8674	0.019*
H4B	0.7293	0.4029	0.8547	0.019*
C5	0.92998 (18)	0.2982 (2)	0.90640 (4)	0.0218 (2)
H5A	1.0150	0.4019	0.9036	0.026*
H5B	0.8787	0.3537	0.9266	0.026*
C6	1.09951 (17)	0.0329 (2)	0.89351 (4)	0.0217 (3)
H6A	1.1638	−0.0976	0.9046	0.026*
H6B	1.1843	0.1392	0.8916	0.026*
C7	0.96949 (16)	−0.0085 (2)	0.85035 (4)	0.0172 (2)
H7A	1.0318	−0.0531	0.8315	0.021*
H7B	0.8908	−0.1235	0.8518	0.021*
O5	0.67215 (12)	0.77378 (16)	0.70574 (3)	0.01897 (18)
H5C	0.6475	0.6819	0.6866	0.028*
H5D	0.6898	0.8942	0.6973	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01181 (11)	0.00864 (10)	0.01302 (11)	0.00155 (9)	0.00290 (8)	−0.00054 (9)
O1	0.0182 (4)	0.0215 (5)	0.0205 (4)	−0.0009 (3)	0.0101 (3)	−0.0045 (3)
O2	0.0142 (4)	0.0159 (4)	0.0181 (4)	0.0046 (3)	−0.0015 (3)	−0.0014 (3)
O3	0.0255 (5)	0.0091 (4)	0.0225 (4)	−0.0013 (3)	0.0062 (4)	0.0005 (3)
C8	0.0140 (4)	0.0111 (4)	0.0121 (4)	0.0009 (4)	0.0037 (4)	0.0007 (4)
C9	0.0205 (5)	0.0162 (5)	0.0181 (5)	0.0045 (4)	0.0009 (4)	0.0003 (4)
C10	0.0223 (6)	0.0236 (6)	0.0154 (5)	0.0011 (5)	−0.0009 (4)	0.0013 (5)
C11	0.0230 (6)	0.0216 (6)	0.0137 (5)	−0.0045 (5)	0.0057 (4)	−0.0024 (4)
C12	0.0285 (6)	0.0157 (5)	0.0168 (5)	0.0018 (5)	0.0076 (5)	−0.0031 (4)
C13	0.0210 (5)	0.0136 (5)	0.0140 (5)	0.0040 (4)	0.0049 (4)	−0.0005 (4)
C14	0.0362 (8)	0.0303 (8)	0.0166 (6)	−0.0072 (6)	0.0056 (5)	−0.0072 (5)
O4	0.0228 (5)	0.0346 (6)	0.0169 (4)	0.0024 (4)	0.0061 (4)	0.0081 (4)
N1	0.0104 (4)	0.0112 (4)	0.0138 (4)	−0.0013 (3)	0.0041 (3)	−0.0001 (3)
N2	0.0107 (4)	0.0146 (4)	0.0144 (4)	−0.0023 (3)	0.0038 (3)	0.0023 (3)
N3	0.0143 (4)	0.0197 (5)	0.0180 (5)	−0.0023 (4)	0.0018 (4)	0.0067 (4)
C1	0.0145 (5)	0.0177 (5)	0.0141 (5)	−0.0044 (4)	0.0009 (4)	−0.0025 (4)
C2	0.0119 (4)	0.0202 (5)	0.0139 (5)	−0.0018 (4)	0.0008 (4)	0.0012 (4)
C3	0.0111 (4)	0.0142 (5)	0.0129 (4)	0.0000 (4)	0.0034 (4)	−0.0002 (4)
C4	0.0137 (4)	0.0181 (5)	0.0166 (5)	0.0006 (4)	0.0075 (4)	−0.0008 (4)
C5	0.0231 (6)	0.0272 (7)	0.0145 (5)	−0.0021 (5)	0.0057 (4)	−0.0025 (5)
C6	0.0153 (5)	0.0270 (7)	0.0219 (6)	0.0035 (5)	0.0052 (4)	0.0101 (5)
C7	0.0165 (5)	0.0132 (5)	0.0222 (6)	0.0024 (4)	0.0070 (4)	0.0035 (4)
O5	0.0206 (4)	0.0172 (4)	0.0175 (4)	−0.0011 (3)	0.0045 (3)	0.0017 (3)

Geometric parameters (Å, º)

S1—O1	1.4565 (10)	N2—C3	1.3092 (15)
S1—O2	1.4654 (9)	N3—H3A	0.8800
S1—O3	1.4602 (10)	N3—H3B	0.8800
S1—C8	1.7740 (12)	N3—C3	1.3348 (16)
C8—C9	1.3995 (17)	C1—H1A	0.9900
C8—C13	1.3884 (17)	C1—H1B	0.9900
C9—H9	0.9500	C1—C2	1.5159 (18)
C9—C10	1.3949 (19)	C2—H2A	0.9900
C10—H10	0.9500	C2—H2B	0.9900
C10—C11	1.398 (2)	C2—C3	1.5086 (16)
C11—C12	1.3941 (19)	C4—H4A	0.9900
C11—C14	1.5108 (19)	C4—H4B	0.9900
C12—H12	0.9500	C4—C5	1.5166 (18)
C12—C13	1.3947 (18)	C5—H5A	0.9900
C13—H13	0.9500	C5—H5B	0.9900
C14—H14A	0.9800	C6—H6A	0.9900
C14—H14B	0.9800	C6—H6B	0.9900
C14—H14C	0.9800	C6—C7	1.5183 (19)
O4—C5	1.4266 (19)	C7—H7A	0.9900
O4—C6	1.4289 (18)	C7—H7B	0.9900
N1—N2	1.4737 (14)	O5—H5C	0.8501
N1—C1	1.5163 (15)	O5—H5C	0.8501
N1—C4	1.5149 (15)	O5—H5D	0.8502
N1—C7	1.5041 (16)
O1—S1—O2	112.24 (6)	N1—C1—H1B	111.4
O1—S1—O3	112.95 (6)	H1A—C1—H1B	109.2
O1—S1—C8	106.11 (6)	C2—C1—N1	101.98 (9)
O2—S1—C8	106.35 (5)	C2—C1—H1A	111.4
O3—S1—O2	112.32 (6)	C2—C1—H1B	111.4
O3—S1—C8	106.25 (6)	C1—C2—H2A	111.7
C9—C8—S1	119.79 (9)	C1—C2—H2B	111.7
C13—C8—S1	119.78 (9)	H2A—C2—H2B	109.5
C13—C8—C9	120.31 (11)	C3—C2—C1	100.21 (9)
C8—C9—H9	120.3	C3—C2—H2A	111.7
C10—C9—C8	119.30 (12)	C3—C2—H2B	111.7
C10—C9—H9	120.3	N2—C3—N3	122.54 (11)
C9—C10—H10	119.4	N2—C3—C2	115.47 (11)
C9—C10—C11	121.13 (12)	N3—C3—C2	121.98 (10)
C11—C10—H10	119.4	N1—C4—H4A	109.6
C10—C11—C14	120.99 (13)	N1—C4—H4B	109.6
C12—C11—C10	118.44 (12)	N1—C4—C5	110.13 (10)
C12—C11—C14	120.57 (13)	H4A—C4—H4B	108.1
C11—C12—H12	119.4	C5—C4—H4A	109.6
C11—C12—C13	121.22 (12)	C5—C4—H4B	109.6
C13—C12—H12	119.4	O4—C5—C4	110.96 (12)
C8—C13—C12	119.58 (12)	O4—C5—H5A	109.4
C8—C13—H13	120.2	O4—C5—H5B	109.4
C12—C13—H13	120.2	C4—C5—H5A	109.4
C11—C14—H14A	109.5	C4—C5—H5B	109.4
C11—C14—H14B	109.5	H5A—C5—H5B	108.0
C11—C14—H14C	109.5	O4—C6—H6A	109.3
H14A—C14—H14B	109.5	O4—C6—H6B	109.3
H14A—C14—H14C	109.5	O4—C6—C7	111.74 (11)
H14B—C14—H14C	109.5	H6A—C6—H6B	107.9
C5—O4—C6	109.17 (10)	C7—C6—H6A	109.3
N2—N1—C1	106.70 (9)	C7—C6—H6B	109.3
N2—N1—C4	109.42 (9)	N1—C7—C6	110.85 (11)
N2—N1—C7	109.10 (9)	N1—C7—H7A	109.5
C4—N1—C1	110.44 (9)	N1—C7—H7B	109.5
C7—N1—C1	111.98 (10)	C6—C7—H7A	109.5
C7—N1—C4	109.14 (9)	C6—C7—H7B	109.5
C3—N2—N1	105.64 (9)	H7A—C7—H7B	108.1
H3A—N3—H3B	120.0	H5C—O5—H5C	0.0
C3—N3—H3A	120.0	H5C—O5—H5D	112.8
C3—N3—H3B	120.0	H5C—O5—H5D	112.8
N1—C1—H1A	111.4

2-Amino-8-thia-1,5-diazaspiro[4.5]dec-1-en-5-ium 4-methylbenzenesulfonate (8)

Crystal data

C7H14N3S^+·C7H7O3S^−	Z = 2
Mr = 343.46	F(000) = 364
Triclinic, P1	Dx = 1.357 Mg m^−3
a = 6.2286 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.5209 (4) Å	Cell parameters from 6761 reflections
c = 16.2157 (7) Å	θ = 2.4–30.5°
α = 84.881 (2)°	µ = 0.33 mm^−1
β = 79.671 (2)°	T = 295 K
γ = 84.660 (2)°	Plate, colourless
V = 840.68 (8) Å^3	0.24 × 0.16 × 0.04 mm

Data collection

Bruker D8 Quest PHOTON area detector diffractometer	4011 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.064
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θmax = 30.5°, θmin = 2.4°
Tmin = 0.389, Tmax = 0.746	h = −8→8
13223 measured reflections	k = −11→12
4869 independent reflections	l = −22→22

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.097	H-atom parameters constrained
wR(F^2) = 0.218	w = 1/[σ^2(Fo^2) + (0.010P)^2 + 2.0384P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
4869 reflections	Δρmax = 1.70 e Å^−3
200 parameters	Δρmin = −0.57 e Å^−3
18 restraints

Special details

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. Single crystals were obtained from reaction mixtures. The intensities of reflections for the samples were measured with a Bruker Quest diffractometer using MoK_? radiation with multilayer optics (? = 0.71073Å)at 100.0 (2) (6, 7, 7·H₂O, 9, 10) or 295.0 (2) K (8a). The structures were solved by the direct method and refined by full-matrix least squares against F². Non-hydrogen atoms were refined anisotropically.

All calculations were made using the SHELXL ??(Sheldrick, 2015a)? and OLEX2 ??(Dolomanov et al., 2009)?] program packages. Experimental details and crystal parameters are listed in Table 1.

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

	x	y	z	Uiso*/Ueq
S1	0.06650 (13)	0.21138 (9)	0.84507 (5)	0.0369 (2)
O1	0.0910 (7)	0.3405 (5)	0.8930 (2)	0.0953 (13)
O2	0.1327 (7)	0.0588 (4)	0.8768 (3)	0.0983 (13)
O3	−0.1582 (5)	0.2148 (5)	0.8334 (2)	0.0807 (10)
C8	0.2284 (5)	0.2441 (3)	0.74419 (18)	0.0345 (6)
C9	0.4255 (6)	0.3104 (5)	0.7344 (2)	0.0485 (8)
H9	0.4722	0.3450	0.7806	0.058*
C10	0.5534 (7)	0.3252 (6)	0.6556 (3)	0.0627 (11)
H10	0.6869	0.3693	0.6495	0.075*
C11	0.4883 (7)	0.2762 (6)	0.5858 (2)	0.0608 (10)
C12	0.2903 (8)	0.2099 (6)	0.5965 (2)	0.0640 (11)
H12	0.2441	0.1755	0.5502	0.077*
C13	0.1594 (6)	0.1938 (5)	0.6747 (2)	0.0524 (9)
H13	0.0260	0.1494	0.6808	0.063*
C14	0.6321 (11)	0.2906 (9)	0.4998 (3)	0.104 (2)
H14A	0.7310	0.3710	0.4985	0.155*
H14B	0.5419	0.3184	0.4577	0.155*
H14C	0.7142	0.1914	0.4888	0.155*
S2	0.8446 (2)	0.77266 (18)	0.64125 (7)	0.0732 (4)
N1	0.6906 (4)	0.7734 (3)	0.84033 (16)	0.0374 (5)
N2	0.5414 (4)	0.6457 (3)	0.85721 (16)	0.0375 (5)
N3	0.2608 (5)	0.5778 (4)	0.96441 (18)	0.0457 (7)
H3A	0.2324	0.5006	0.9384	0.055*
H3B	0.1852	0.5968	1.0128	0.055*
C1	0.6943 (7)	0.8381 (5)	0.9239 (2)	0.0578 (10)
H1A	0.7131	0.9505	0.9172	0.069*
H1B	0.8103	0.7839	0.9508	0.069*
C2	0.4705 (6)	0.8047 (4)	0.9734 (2)	0.0480 (8)
H2A	0.4761	0.7760	1.0323	0.058*
H2B	0.3643	0.8944	0.9686	0.058*
C3	0.4212 (5)	0.6676 (3)	0.92986 (19)	0.0355 (6)
C4	0.9151 (6)	0.7088 (5)	0.8040 (2)	0.0490 (8)
H4A	0.9673	0.6295	0.8441	0.059*
H4B	1.0128	0.7933	0.7950	0.059*
C5	0.9237 (7)	0.6359 (5)	0.7219 (3)	0.0571 (10)
H5A	0.8279	0.5502	0.7312	0.069*
H5B	1.0716	0.5912	0.7032	0.069*
C6	0.5830 (7)	0.8394 (6)	0.6995 (3)	0.0636 (11)
H6A	0.5142	0.9224	0.6659	0.076*
H6B	0.4893	0.7524	0.7104	0.076*
C7	0.6030 (6)	0.9005 (4)	0.7813 (2)	0.0499 (8)
H7A	0.4604	0.9436	0.8080	0.060*
H7B	0.7000	0.9855	0.7706	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0437 (4)	0.0326 (4)	0.0331 (4)	−0.0058 (3)	−0.0012 (3)	−0.0037 (3)
O1	0.124 (3)	0.097 (2)	0.0675 (19)	−0.063 (2)	0.0222 (18)	−0.0408 (18)
O2	0.103 (2)	0.072 (2)	0.088 (2)	0.0258 (18)	0.0342 (19)	0.0316 (17)
O3	0.0597 (18)	0.110 (3)	0.0668 (19)	−0.0114 (17)	0.0013 (15)	0.0018 (18)
C8	0.0380 (15)	0.0311 (13)	0.0335 (14)	−0.0020 (11)	−0.0045 (11)	−0.0023 (10)
C9	0.0439 (18)	0.059 (2)	0.0437 (18)	−0.0130 (15)	−0.0028 (14)	−0.0100 (15)
C10	0.048 (2)	0.078 (3)	0.059 (2)	−0.0210 (19)	0.0072 (17)	−0.008 (2)
C11	0.064 (2)	0.072 (3)	0.0394 (18)	−0.004 (2)	0.0076 (17)	−0.0014 (17)
C12	0.071 (3)	0.088 (3)	0.0350 (18)	−0.012 (2)	−0.0081 (17)	−0.0115 (19)
C13	0.054 (2)	0.069 (2)	0.0378 (17)	−0.0166 (18)	−0.0095 (15)	−0.0060 (16)
C14	0.104 (4)	0.141 (6)	0.053 (3)	−0.025 (4)	0.031 (3)	−0.011 (3)
S2	0.0749 (8)	0.1005 (10)	0.0369 (5)	−0.0010 (6)	0.0091 (5)	−0.0094 (5)
N1	0.0454 (14)	0.0325 (12)	0.0337 (12)	−0.0111 (10)	−0.0002 (10)	−0.0047 (9)
N2	0.0447 (14)	0.0326 (12)	0.0351 (12)	−0.0099 (10)	−0.0015 (10)	−0.0060 (9)
N3	0.0459 (15)	0.0479 (16)	0.0419 (14)	−0.0149 (12)	0.0018 (12)	−0.0038 (12)
C1	0.077 (3)	0.061 (2)	0.0390 (17)	−0.034 (2)	0.0022 (17)	−0.0170 (16)
C2	0.066 (2)	0.0415 (17)	0.0354 (16)	−0.0123 (15)	0.0022 (14)	−0.0095 (13)
C3	0.0389 (15)	0.0328 (13)	0.0340 (14)	−0.0029 (11)	−0.0042 (11)	−0.0024 (10)
C4	0.0392 (17)	0.056 (2)	0.0509 (19)	−0.0048 (15)	−0.0058 (14)	−0.0018 (16)
C5	0.049 (2)	0.057 (2)	0.061 (2)	0.0028 (17)	0.0070 (17)	−0.0183 (18)
C6	0.063 (2)	0.080 (3)	0.0414 (19)	0.006 (2)	−0.0062 (17)	0.0109 (18)
C7	0.058 (2)	0.0332 (15)	0.0490 (19)	0.0052 (14)	0.0080 (16)	0.0027 (13)

Geometric parameters (Å, º)

S1—O1	1.437 (3)	N1—C4	1.492 (4)
S1—O2	1.408 (3)	N1—C7	1.510 (4)
S1—O3	1.443 (3)	N2—C3	1.296 (4)
S1—C8	1.775 (3)	N3—H3A	0.8600
C8—C9	1.376 (4)	N3—H3B	0.8600
C8—C13	1.390 (4)	N3—C3	1.328 (4)
C9—H9	0.9300	C1—H1A	0.9700
C9—C10	1.381 (5)	C1—H1B	0.9700
C10—H10	0.9300	C1—C2	1.517 (5)
C10—C11	1.378 (6)	C2—H2A	0.9700
C11—C12	1.380 (6)	C2—H2B	0.9700
C11—C14	1.519 (6)	C2—C3	1.500 (4)
C12—H12	0.9300	C4—H4A	0.9700
C12—C13	1.382 (5)	C4—H4B	0.9700
C13—H13	0.9300	C4—C5	1.509 (5)
C14—H14A	0.9600	C5—H5A	0.9700
C14—H14B	0.9600	C5—H5B	0.9700
C14—H14C	0.9600	C6—H6A	0.9700
S2—C5	1.779 (5)	C6—H6B	0.9700
S2—C6	1.801 (4)	C6—C7	1.497 (6)
N1—N2	1.472 (3)	C7—H7A	0.9700
N1—C1	1.512 (4)	C7—H7B	0.9700
O1—S1—O3	109.4 (3)	C3—N3—H3B	120.0
O1—S1—C8	107.08 (18)	N1—C1—H1A	111.3
O2—S1—O1	116.8 (3)	N1—C1—H1B	111.3
O2—S1—O3	109.0 (3)	N1—C1—C2	102.5 (3)
O2—S1—C8	106.86 (18)	H1A—C1—H1B	109.2
O3—S1—C8	107.25 (18)	C2—C1—H1A	111.3
C9—C8—S1	121.1 (2)	C2—C1—H1B	111.3
C9—C8—C13	119.8 (3)	C1—C2—H2A	111.6
C13—C8—S1	119.0 (3)	C1—C2—H2B	111.6
C8—C9—H9	120.2	H2A—C2—H2B	109.4
C8—C9—C10	119.5 (3)	C3—C2—C1	100.6 (3)
C10—C9—H9	120.2	C3—C2—H2A	111.6
C9—C10—H10	119.1	C3—C2—H2B	111.6
C11—C10—C9	121.7 (4)	N2—C3—N3	123.2 (3)
C11—C10—H10	119.1	N2—C3—C2	115.9 (3)
C10—C11—C12	118.1 (4)	N3—C3—C2	120.9 (3)
C10—C11—C14	121.2 (5)	N1—C4—H4A	109.0
C12—C11—C14	120.6 (5)	N1—C4—H4B	109.0
C11—C12—H12	119.4	N1—C4—C5	112.9 (3)
C11—C12—C13	121.2 (4)	H4A—C4—H4B	107.8
C13—C12—H12	119.4	C5—C4—H4A	109.0
C8—C13—H13	120.2	C5—C4—H4B	109.0
C12—C13—C8	119.6 (4)	S2—C5—H5A	108.9
C12—C13—H13	120.2	S2—C5—H5B	108.9
C11—C14—H14A	109.5	C4—C5—S2	113.4 (3)
C11—C14—H14B	109.5	C4—C5—H5A	108.9
C11—C14—H14C	109.5	C4—C5—H5B	108.9
H14A—C14—H14B	109.5	H5A—C5—H5B	107.7
H14A—C14—H14C	109.5	S2—C6—H6A	109.2
H14B—C14—H14C	109.5	S2—C6—H6B	109.2
C5—S2—C6	96.39 (18)	H6A—C6—H6B	107.9
N2—N1—C1	106.8 (2)	C7—C6—S2	112.2 (3)
N2—N1—C4	109.9 (2)	C7—C6—H6A	109.2
N2—N1—C7	108.9 (3)	C7—C6—H6B	109.2
C4—N1—C1	109.6 (3)	N1—C7—H7A	109.2
C4—N1—C7	111.3 (3)	N1—C7—H7B	109.2
C7—N1—C1	110.2 (3)	C6—C7—N1	112.2 (3)
C3—N2—N1	106.2 (2)	C6—C7—H7A	109.2
H3A—N3—H3B	120.0	C6—C7—H7B	109.2
C3—N3—H3A	120.0	H7A—C7—H7B	107.9

2-Amino-8-phenyl-1,5,8-triazaspiro[4.5]dec-1-en-5-ium 4-methylbenzenesulfonate (9)

Crystal data

C13H19N4^+·C7H7O3S^−	Z = 4
Mr = 402.51	F(000) = 856
Triclinic, P1	Dx = 1.338 Mg m^−3
a = 8.4423 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.0126 (4) Å	Cell parameters from 5975 reflections
c = 20.3063 (6) Å	θ = 2.4–30.5°
α = 100.315 (1)°	µ = 0.19 mm^−1
β = 96.533 (1)°	T = 100 K
γ = 95.678 (2)°	Plate, colourless
V = 1997.85 (11) Å^3	0.28 × 0.16 × 0.03 mm

Data collection

Bruker D8 Quest PHOTON detector diffractometer	8283 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.067
phi and ω scans	θmax = 30.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −12→12
Tmin = 0.693, Tmax = 0.746	k = −17→16
32048 measured reflections	l = −29→28
12050 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.053	H-atom parameters constrained
wR(F^2) = 0.128	w = 1/[σ^2(Fo^2) + (0.047P)^2 + 0.5831P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.005
12050 reflections	Δρmax = 0.44 e Å^−3
507 parameters	Δρmin = −0.51 e Å^−3
0 restraints

Special details

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. Single crystals were obtained from reaction mixtures. The intensities of reflections for the samples were measured with a Bruker Quest diffractometer using MoK_? radiation with multilayer optics (? = 0.71073Å)at 100.0 (2) (6, 7, 7·H₂O, 9, 10) or 295.0 (2) K (8a). The structures were solved by the direct method and refined by full-matrix least squares against F². Non-hydrogen atoms were refined anisotropically.

All calculations were made using the SHELXL ??(Sheldrick, 2015a)? and OLEX2 ??(Dolomanov et al., 2009)?] program packages. Experimental details and crystal parameters are listed in Table 1.

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

	x	y	z	Uiso*/Ueq
S1A	0.22897 (5)	0.27108 (3)	0.62635 (2)	0.01242 (9)
O1A	0.33527 (16)	0.36856 (11)	0.61689 (6)	0.0205 (3)
O2A	0.25158 (16)	0.16556 (11)	0.58232 (6)	0.0187 (3)
O3A	0.06131 (15)	0.29161 (11)	0.62272 (6)	0.0182 (3)
C14A	0.2841 (2)	0.25202 (14)	0.71034 (8)	0.0143 (3)
C15A	0.2317 (3)	0.32296 (18)	0.76325 (10)	0.0295 (5)
H15A	0.1674	0.3807	0.7545	0.035*
C16A	0.2742 (4)	0.3086 (2)	0.82885 (10)	0.0399 (6)
H16A	0.2383	0.3570	0.8650	0.048*
C17A	0.3684 (3)	0.22468 (19)	0.84311 (10)	0.0303 (5)
C18A	0.4160 (3)	0.15363 (17)	0.78939 (10)	0.0227 (4)
H18A	0.4785	0.0950	0.7981	0.027*
C19A	0.3748 (2)	0.16586 (15)	0.72286 (9)	0.0176 (4)
H19A	0.4082	0.1160	0.6866	0.021*
C20A	0.4125 (4)	0.2097 (2)	0.91504 (11)	0.0496 (8)
H20A	0.4412	0.2847	0.9446	0.074*
H20B	0.5041	0.1658	0.9174	0.074*
H20C	0.3206	0.1689	0.9297	0.074*
S1B	0.76188 (5)	0.20010 (4)	0.37318 (2)	0.01294 (9)
O1B	0.90086 (17)	0.27540 (12)	0.41026 (6)	0.0246 (3)
O2B	0.78796 (18)	0.08137 (11)	0.36021 (6)	0.0214 (3)
O3B	0.61544 (16)	0.21880 (11)	0.40376 (7)	0.0207 (3)
C14B	0.7299 (2)	0.23792 (15)	0.29212 (8)	0.0149 (3)
C15B	0.7849 (2)	0.17221 (15)	0.23751 (9)	0.0190 (4)
H15B	0.8329	0.1056	0.2430	0.023*
C16B	0.7689 (3)	0.20502 (17)	0.17479 (9)	0.0224 (4)
H16B	0.8069	0.1603	0.1377	0.027*
C17B	0.6987 (2)	0.30145 (17)	0.16550 (9)	0.0225 (4)
C18B	0.6424 (3)	0.36536 (17)	0.22052 (10)	0.0249 (4)
H18B	0.5928	0.4312	0.2147	0.030*
C19B	0.6574 (2)	0.33474 (16)	0.28367 (9)	0.0208 (4)
H19B	0.6187	0.3793	0.3206	0.025*
C20B	0.6873 (3)	0.3396 (2)	0.09798 (10)	0.0330 (5)
H20D	0.7812	0.3942	0.0974	0.049*
H20E	0.5893	0.3759	0.0912	0.049*
H20F	0.6842	0.2732	0.0617	0.049*
N1A	0.21592 (18)	0.52737 (12)	0.37860 (7)	0.0127 (3)
N2A	0.33798 (18)	0.45039 (12)	0.38983 (7)	0.0145 (3)
N3A	0.41482 (19)	0.35688 (12)	0.47664 (7)	0.0159 (3)
H3AA	0.4855	0.3235	0.4539	0.019*
H3AB	0.4029	0.3437	0.5172	0.019*
N4A	0.1726 (2)	0.51015 (13)	0.23363 (7)	0.0182 (3)
C1A	0.3258 (2)	0.42746 (14)	0.44972 (8)	0.0138 (3)
C2A	0.2018 (2)	0.48318 (15)	0.48668 (9)	0.0154 (3)
H2AA	0.2439	0.5147	0.5346	0.018*
H2AB	0.1033	0.4297	0.4841	0.018*
C3A	0.1721 (2)	0.57666 (15)	0.44743 (8)	0.0162 (3)
H3AC	0.2415	0.6485	0.4683	0.019*
H3AD	0.0583	0.5910	0.4443	0.019*
C4A	0.0711 (2)	0.46040 (15)	0.33313 (9)	0.0159 (3)
H4AA	−0.0148	0.5101	0.3289	0.019*
H4AB	0.0298	0.3961	0.3534	0.019*
C5A	0.1141 (2)	0.41488 (15)	0.26387 (9)	0.0183 (4)
H5AA	0.1983	0.3637	0.2678	0.022*
H5AB	0.0184	0.3704	0.2348	0.022*
C6A	0.3183 (2)	0.57318 (15)	0.27534 (9)	0.0173 (4)
H6AA	0.3590	0.6365	0.2542	0.021*
H6AB	0.4025	0.5218	0.2781	0.021*
C7A	0.2836 (2)	0.62043 (14)	0.34553 (8)	0.0147 (3)
H7AA	0.3839	0.6604	0.3733	0.018*
H7AB	0.2059	0.6766	0.3430	0.018*
C8A	0.1846 (3)	0.48537 (17)	0.16327 (9)	0.0240 (4)
C9A	0.2072 (4)	0.5767 (2)	0.13014 (11)	0.0434 (7)
H9A	0.2170	0.6526	0.1549	0.052*
C10A	0.2156 (5)	0.5574 (3)	0.06155 (13)	0.0663 (11)
H10A	0.2302	0.6202	0.0394	0.080*
C11A	0.2030 (5)	0.4474 (3)	0.02493 (12)	0.0644 (10)
H11A	0.2097	0.4346	−0.0222	0.077*
C12A	0.1806 (4)	0.3565 (2)	0.05725 (12)	0.0472 (7)
H12A	0.1717	0.2808	0.0323	0.057*
C13A	0.1710 (3)	0.37502 (19)	0.12624 (10)	0.0316 (5)
H13A	0.1551	0.3120	0.1481	0.038*
N1B	0.80637 (18)	−0.00380 (12)	0.63126 (7)	0.0144 (3)
N2B	0.65824 (18)	0.04813 (12)	0.61763 (7)	0.0148 (3)
N3B	0.55495 (19)	0.13834 (12)	0.53314 (7)	0.0160 (3)
H3BA	0.4700	0.1519	0.5533	0.019*
H3BB	0.5657	0.1608	0.4948	0.019*
N4B	0.81343 (19)	−0.01232 (13)	0.77410 (7)	0.0177 (3)
C1B	0.6674 (2)	0.08371 (14)	0.56074 (8)	0.0140 (3)
C2B	0.8150 (2)	0.06218 (15)	0.52832 (9)	0.0166 (3)
H2BA	0.8920	0.1323	0.5354	0.020*
H2BB	0.7883	0.0311	0.4793	0.020*
C3B	0.8799 (2)	−0.02526 (17)	0.56597 (9)	0.0193 (4)
H3BC	0.9987	−0.0129	0.5748	0.023*
H3BD	0.8450	−0.1038	0.5404	0.023*
C4B	0.9214 (2)	0.07556 (15)	0.68588 (9)	0.0162 (3)
H4BA	0.9455	0.1493	0.6716	0.019*
H4BB	1.0234	0.0423	0.6926	0.019*
C5B	0.8518 (2)	0.09573 (15)	0.75176 (9)	0.0175 (4)
H5BA	0.9301	0.1473	0.7867	0.021*
H5BB	0.7531	0.1331	0.7458	0.021*
C6B	0.7008 (2)	−0.09183 (15)	0.72248 (9)	0.0171 (4)
H6BA	0.5973	−0.0602	0.7164	0.021*
H6BB	0.6803	−0.1651	0.7377	0.021*
C7B	0.7668 (2)	−0.11262 (15)	0.65576 (9)	0.0178 (4)
H7BA	0.8650	−0.1507	0.6610	0.021*
H7BB	0.6867	−0.1643	0.6216	0.021*
C8B	0.7837 (2)	−0.00414 (16)	0.84190 (9)	0.0190 (4)
C9B	0.6624 (3)	−0.07563 (17)	0.86021 (10)	0.0229 (4)
H9B	0.5940	−0.1295	0.8263	0.028*
C10B	0.6412 (3)	−0.06842 (19)	0.92796 (10)	0.0296 (5)
H10B	0.5592	−0.1185	0.9396	0.036*
C11B	0.7363 (3)	0.0094 (2)	0.97812 (10)	0.0344 (5)
H11B	0.7201	0.0142	1.0240	0.041*
C12B	0.8566 (4)	0.0810 (2)	0.96025 (11)	0.0461 (7)
H12B	0.9233	0.1356	0.9944	0.055*
C13B	0.8809 (3)	0.0739 (2)	0.89359 (10)	0.0362 (6)
H13B	0.9651	0.1230	0.8827	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0109 (2)	0.01409 (19)	0.01302 (19)	0.00214 (15)	0.00159 (15)	0.00424 (15)
O1A	0.0181 (7)	0.0231 (7)	0.0205 (6)	−0.0035 (5)	0.0010 (5)	0.0090 (5)
O2A	0.0214 (7)	0.0193 (6)	0.0152 (6)	0.0073 (5)	0.0017 (5)	0.0006 (5)
O3A	0.0116 (6)	0.0232 (6)	0.0219 (6)	0.0059 (5)	0.0030 (5)	0.0074 (5)
C14A	0.0147 (9)	0.0152 (8)	0.0132 (7)	0.0019 (6)	0.0017 (6)	0.0038 (6)
C15A	0.0462 (14)	0.0291 (10)	0.0180 (9)	0.0236 (10)	0.0061 (9)	0.0058 (8)
C16A	0.0690 (19)	0.0404 (13)	0.0150 (9)	0.0306 (13)	0.0078 (11)	0.0032 (9)
C17A	0.0427 (14)	0.0339 (11)	0.0169 (9)	0.0115 (10)	0.0025 (9)	0.0093 (8)
C18A	0.0237 (11)	0.0258 (10)	0.0218 (9)	0.0077 (8)	0.0021 (8)	0.0109 (8)
C19A	0.0166 (9)	0.0196 (8)	0.0186 (8)	0.0059 (7)	0.0037 (7)	0.0057 (7)
C20A	0.076 (2)	0.0620 (17)	0.0180 (10)	0.0335 (16)	0.0039 (12)	0.0153 (11)
S1B	0.0125 (2)	0.01444 (19)	0.01266 (19)	0.00213 (15)	0.00245 (15)	0.00379 (15)
O1B	0.0239 (8)	0.0305 (7)	0.0165 (6)	−0.0107 (6)	−0.0032 (5)	0.0078 (6)
O2B	0.0297 (8)	0.0186 (6)	0.0190 (6)	0.0114 (6)	0.0048 (6)	0.0062 (5)
O3B	0.0187 (7)	0.0273 (7)	0.0213 (6)	0.0101 (6)	0.0101 (5)	0.0105 (5)
C14B	0.0134 (9)	0.0181 (8)	0.0135 (8)	0.0001 (7)	0.0016 (6)	0.0048 (6)
C15B	0.0234 (10)	0.0165 (8)	0.0165 (8)	0.0017 (7)	0.0027 (7)	0.0019 (7)
C16B	0.0276 (11)	0.0242 (9)	0.0137 (8)	−0.0003 (8)	0.0027 (7)	0.0013 (7)
C17B	0.0209 (10)	0.0294 (10)	0.0171 (8)	−0.0025 (8)	−0.0005 (7)	0.0093 (8)
C18B	0.0250 (11)	0.0282 (10)	0.0266 (10)	0.0093 (8)	0.0042 (8)	0.0151 (8)
C19B	0.0227 (10)	0.0235 (9)	0.0200 (9)	0.0082 (8)	0.0067 (8)	0.0088 (7)
C20B	0.0394 (14)	0.0414 (13)	0.0205 (10)	0.0022 (10)	0.0027 (9)	0.0145 (9)
N1A	0.0117 (7)	0.0130 (6)	0.0138 (7)	0.0028 (5)	0.0013 (5)	0.0032 (5)
N2A	0.0135 (7)	0.0153 (7)	0.0162 (7)	0.0056 (6)	0.0021 (6)	0.0046 (5)
N3A	0.0172 (8)	0.0169 (7)	0.0159 (7)	0.0066 (6)	0.0040 (6)	0.0057 (6)
N4A	0.0227 (9)	0.0194 (7)	0.0123 (7)	−0.0008 (6)	0.0024 (6)	0.0042 (6)
C1A	0.0135 (8)	0.0127 (7)	0.0149 (8)	0.0009 (6)	0.0016 (6)	0.0025 (6)
C2A	0.0153 (9)	0.0173 (8)	0.0155 (8)	0.0041 (7)	0.0043 (7)	0.0055 (6)
C3A	0.0174 (9)	0.0180 (8)	0.0143 (8)	0.0062 (7)	0.0040 (7)	0.0027 (6)
C4A	0.0122 (8)	0.0168 (8)	0.0185 (8)	−0.0009 (7)	0.0011 (7)	0.0050 (7)
C5A	0.0210 (10)	0.0152 (8)	0.0176 (8)	−0.0017 (7)	0.0013 (7)	0.0032 (7)
C6A	0.0191 (9)	0.0175 (8)	0.0165 (8)	0.0008 (7)	0.0054 (7)	0.0056 (7)
C7A	0.0148 (9)	0.0132 (8)	0.0165 (8)	0.0010 (6)	0.0018 (6)	0.0048 (6)
C8A	0.0295 (11)	0.0289 (10)	0.0144 (8)	0.0048 (9)	0.0035 (8)	0.0050 (7)
C9A	0.080 (2)	0.0346 (12)	0.0193 (10)	0.0101 (13)	0.0140 (12)	0.0082 (9)
C10A	0.125 (3)	0.0551 (17)	0.0232 (12)	0.0072 (19)	0.0202 (16)	0.0160 (12)
C11A	0.111 (3)	0.0659 (19)	0.0147 (11)	0.004 (2)	0.0165 (15)	0.0024 (12)
C12A	0.065 (2)	0.0464 (15)	0.0242 (11)	−0.0029 (14)	0.0125 (12)	−0.0082 (10)
C13A	0.0395 (14)	0.0316 (11)	0.0208 (10)	−0.0001 (10)	0.0067 (9)	−0.0018 (8)
N1B	0.0125 (7)	0.0180 (7)	0.0137 (7)	0.0054 (6)	0.0030 (6)	0.0024 (5)
N2B	0.0113 (7)	0.0192 (7)	0.0149 (7)	0.0055 (6)	0.0032 (6)	0.0032 (6)
N3B	0.0173 (8)	0.0166 (7)	0.0156 (7)	0.0048 (6)	0.0031 (6)	0.0049 (6)
N4B	0.0194 (8)	0.0183 (7)	0.0146 (7)	−0.0015 (6)	0.0017 (6)	0.0035 (6)
C1B	0.0148 (9)	0.0127 (8)	0.0131 (7)	−0.0002 (6)	0.0018 (6)	0.0001 (6)
C2B	0.0152 (9)	0.0204 (8)	0.0146 (8)	0.0034 (7)	0.0045 (7)	0.0023 (7)
C3B	0.0173 (9)	0.0283 (10)	0.0144 (8)	0.0101 (8)	0.0065 (7)	0.0024 (7)
C4B	0.0135 (9)	0.0186 (8)	0.0165 (8)	0.0009 (7)	0.0014 (7)	0.0039 (7)
C5B	0.0187 (9)	0.0165 (8)	0.0167 (8)	−0.0014 (7)	0.0023 (7)	0.0030 (7)
C6B	0.0189 (9)	0.0153 (8)	0.0160 (8)	−0.0012 (7)	0.0002 (7)	0.0030 (6)
C7B	0.0207 (10)	0.0152 (8)	0.0170 (8)	0.0041 (7)	0.0004 (7)	0.0022 (6)
C8B	0.0192 (10)	0.0230 (9)	0.0154 (8)	0.0024 (7)	0.0028 (7)	0.0053 (7)
C9B	0.0262 (11)	0.0229 (9)	0.0203 (9)	−0.0001 (8)	0.0049 (8)	0.0062 (7)
C10B	0.0336 (13)	0.0343 (11)	0.0239 (10)	0.0010 (10)	0.0098 (9)	0.0117 (9)
C11B	0.0451 (15)	0.0433 (13)	0.0165 (9)	0.0028 (11)	0.0087 (9)	0.0086 (9)
C12B	0.0576 (18)	0.0558 (16)	0.0160 (10)	−0.0207 (14)	−0.0003 (10)	0.0019 (10)
C13B	0.0388 (14)	0.0472 (14)	0.0170 (9)	−0.0170 (11)	0.0007 (9)	0.0048 (9)

Geometric parameters (Å, º)

S1A—O1A	1.4578 (13)	C5A—H5AA	0.9900
S1A—O2A	1.4572 (13)	C5A—H5AB	0.9900
S1A—O3A	1.4565 (14)	C6A—H6AA	0.9900
S1A—C14A	1.7771 (17)	C6A—H6AB	0.9900
C14A—C15A	1.390 (3)	C6A—C7A	1.509 (2)
C14A—C19A	1.389 (3)	C7A—H7AA	0.9900
C15A—H15A	0.9500	C7A—H7AB	0.9900
C15A—C16A	1.385 (3)	C8A—C9A	1.394 (3)
C16A—H16A	0.9500	C8A—C13A	1.389 (3)
C16A—C17A	1.394 (3)	C9A—H9A	0.9500
C17A—C18A	1.383 (3)	C9A—C10A	1.382 (3)
C17A—C20A	1.513 (3)	C10A—H10A	0.9500
C18A—H18A	0.9500	C10A—C11A	1.383 (4)
C18A—C19A	1.394 (2)	C11A—H11A	0.9500
C19A—H19A	0.9500	C11A—C12A	1.380 (4)
C20A—H20A	0.9800	C12A—H12A	0.9500
C20A—H20B	0.9800	C12A—C13A	1.391 (3)
C20A—H20C	0.9800	C13A—H13A	0.9500
S1B—O1B	1.4515 (13)	N1B—N2B	1.472 (2)
S1B—O2B	1.4466 (13)	N1B—C3B	1.519 (2)
S1B—O3B	1.4643 (14)	N1B—C4B	1.508 (2)
S1B—C14B	1.7831 (17)	N1B—C7B	1.501 (2)
C14B—C15B	1.394 (3)	N2B—C1B	1.309 (2)
C14B—C19B	1.395 (3)	N3B—H3BA	0.8800
C15B—H15B	0.9500	N3B—H3BB	0.8800
C15B—C16B	1.395 (3)	N3B—C1B	1.334 (2)
C16B—H16B	0.9500	N4B—C5B	1.469 (2)
C16B—C17B	1.385 (3)	N4B—C6B	1.466 (2)
C17B—C18B	1.396 (3)	N4B—C8B	1.416 (2)
C17B—C20B	1.517 (3)	C1B—C2B	1.498 (3)
C18B—H18B	0.9500	C2B—H2BA	0.9900
C18B—C19B	1.392 (3)	C2B—H2BB	0.9900
C19B—H19B	0.9500	C2B—C3B	1.515 (3)
C20B—H20D	0.9800	C3B—H3BC	0.9900
C20B—H20E	0.9800	C3B—H3BD	0.9900
C20B—H20F	0.9800	C4B—H4BA	0.9900
N1A—N2A	1.476 (2)	C4B—H4BB	0.9900
N1A—C3A	1.518 (2)	C4B—C5B	1.512 (2)
N1A—C4A	1.509 (2)	C5B—H5BA	0.9900
N1A—C7A	1.502 (2)	C5B—H5BB	0.9900
N2A—C1A	1.307 (2)	C6B—H6BA	0.9900
N3A—H3AA	0.8800	C6B—H6BB	0.9900
N3A—H3AB	0.8800	C6B—C7B	1.512 (2)
N3A—C1A	1.335 (2)	C7B—H7BA	0.9900
N4A—C5A	1.463 (2)	C7B—H7BB	0.9900
N4A—C6A	1.467 (2)	C8B—C9B	1.396 (3)
N4A—C8A	1.424 (2)	C8B—C13B	1.398 (3)
C1A—C2A	1.498 (2)	C9B—H9B	0.9500
C2A—H2AA	0.9900	C9B—C10B	1.396 (3)
C2A—H2AB	0.9900	C10B—H10B	0.9500
C2A—C3A	1.513 (2)	C10B—C11B	1.371 (3)
C3A—H3AC	0.9900	C11B—H11B	0.9500
C3A—H3AD	0.9900	C11B—C12B	1.388 (3)
C4A—H4AA	0.9900	C12B—H12B	0.9500
C4A—H4AB	0.9900	C12B—C13B	1.381 (3)
C4A—C5A	1.513 (2)	C13B—H13B	0.9500
O1A—S1A—C14A	106.64 (8)	N4A—C6A—H6AA	109.5
O2A—S1A—O1A	112.46 (8)	N4A—C6A—H6AB	109.5
O2A—S1A—C14A	106.20 (8)	N4A—C6A—C7A	110.58 (15)
O3A—S1A—O1A	112.85 (8)	H6AA—C6A—H6AB	108.1
O3A—S1A—O2A	112.69 (8)	C7A—C6A—H6AA	109.5
O3A—S1A—C14A	105.32 (8)	C7A—C6A—H6AB	109.5
C15A—C14A—S1A	118.94 (15)	N1A—C7A—C6A	111.26 (13)
C19A—C14A—S1A	120.59 (14)	N1A—C7A—H7AA	109.4
C19A—C14A—C15A	120.45 (17)	N1A—C7A—H7AB	109.4
C14A—C15A—H15A	120.4	C6A—C7A—H7AA	109.4
C16A—C15A—C14A	119.2 (2)	C6A—C7A—H7AB	109.4
C16A—C15A—H15A	120.4	H7AA—C7A—H7AB	108.0
C15A—C16A—H16A	119.2	C9A—C8A—N4A	118.02 (18)
C15A—C16A—C17A	121.6 (2)	C13A—C8A—N4A	123.05 (18)
C17A—C16A—H16A	119.2	C13A—C8A—C9A	118.92 (19)
C16A—C17A—C20A	120.8 (2)	C8A—C9A—H9A	119.8
C18A—C17A—C16A	117.95 (19)	C10A—C9A—C8A	120.4 (2)
C18A—C17A—C20A	121.2 (2)	C10A—C9A—H9A	119.8
C17A—C18A—H18A	119.1	C9A—C10A—H10A	119.8
C17A—C18A—C19A	121.72 (19)	C9A—C10A—C11A	120.5 (3)
C19A—C18A—H18A	119.1	C11A—C10A—H10A	119.8
C14A—C19A—C18A	118.99 (18)	C10A—C11A—H11A	120.2
C14A—C19A—H19A	120.5	C12A—C11A—C10A	119.5 (2)
C18A—C19A—H19A	120.5	C12A—C11A—H11A	120.2
C17A—C20A—H20A	109.5	C11A—C12A—H12A	119.8
C17A—C20A—H20B	109.5	C11A—C12A—C13A	120.4 (2)
C17A—C20A—H20C	109.5	C13A—C12A—H12A	119.8
H20A—C20A—H20B	109.5	C8A—C13A—C12A	120.2 (2)
H20A—C20A—H20C	109.5	C8A—C13A—H13A	119.9
H20B—C20A—H20C	109.5	C12A—C13A—H13A	119.9
O1B—S1B—O3B	112.20 (8)	N2B—N1B—C3B	107.54 (13)
O1B—S1B—C14B	106.29 (8)	N2B—N1B—C4B	109.94 (13)
O2B—S1B—O1B	113.37 (9)	N2B—N1B—C7B	109.48 (13)
O2B—S1B—O3B	112.74 (8)	C4B—N1B—C3B	110.48 (14)
O2B—S1B—C14B	105.47 (8)	C7B—N1B—C3B	111.39 (14)
O3B—S1B—C14B	106.04 (8)	C7B—N1B—C4B	108.02 (13)
C15B—C14B—S1B	119.11 (14)	C1B—N2B—N1B	105.85 (14)
C15B—C14B—C19B	120.08 (16)	H3BA—N3B—H3BB	120.0
C19B—C14B—S1B	120.75 (14)	C1B—N3B—H3BA	120.0
C14B—C15B—H15B	120.2	C1B—N3B—H3BB	120.0
C14B—C15B—C16B	119.50 (18)	C6B—N4B—C5B	110.79 (14)
C16B—C15B—H15B	120.2	C8B—N4B—C5B	116.43 (14)
C15B—C16B—H16B	119.3	C8B—N4B—C6B	116.90 (14)
C17B—C16B—C15B	121.32 (19)	N2B—C1B—N3B	122.89 (17)
C17B—C16B—H16B	119.3	N2B—C1B—C2B	116.08 (16)
C16B—C17B—C18B	118.38 (17)	N3B—C1B—C2B	121.01 (15)
C16B—C17B—C20B	121.21 (19)	C1B—C2B—H2BA	111.5
C18B—C17B—C20B	120.4 (2)	C1B—C2B—H2BB	111.5
C17B—C18B—H18B	119.3	C1B—C2B—C3B	101.15 (14)
C19B—C18B—C17B	121.45 (19)	H2BA—C2B—H2BB	109.4
C19B—C18B—H18B	119.3	C3B—C2B—H2BA	111.5
C14B—C19B—H19B	120.4	C3B—C2B—H2BB	111.5
C18B—C19B—C14B	119.26 (18)	N1B—C3B—H3BC	111.2
C18B—C19B—H19B	120.4	N1B—C3B—H3BD	111.2
C17B—C20B—H20D	109.5	C2B—C3B—N1B	102.81 (14)
C17B—C20B—H20E	109.5	C2B—C3B—H3BC	111.2
C17B—C20B—H20F	109.5	C2B—C3B—H3BD	111.2
H20D—C20B—H20E	109.5	H3BC—C3B—H3BD	109.1
H20D—C20B—H20F	109.5	N1B—C4B—H4BA	109.4
H20E—C20B—H20F	109.5	N1B—C4B—H4BB	109.4
N2A—N1A—C3A	106.90 (12)	N1B—C4B—C5B	111.23 (14)
N2A—N1A—C4A	109.30 (13)	H4BA—C4B—H4BB	108.0
N2A—N1A—C7A	109.84 (13)	C5B—C4B—H4BA	109.4
C4A—N1A—C3A	110.90 (13)	C5B—C4B—H4BB	109.4
C7A—N1A—C3A	110.76 (13)	N4B—C5B—C4B	110.74 (15)
C7A—N1A—C4A	109.11 (13)	N4B—C5B—H5BA	109.5
C1A—N2A—N1A	105.54 (14)	N4B—C5B—H5BB	109.5
H3AA—N3A—H3AB	120.0	C4B—C5B—H5BA	109.5
C1A—N3A—H3AA	120.0	C4B—C5B—H5BB	109.5
C1A—N3A—H3AB	120.0	H5BA—C5B—H5BB	108.1
C5A—N4A—C6A	109.75 (14)	N4B—C6B—H6BA	109.4
C8A—N4A—C5A	116.75 (15)	N4B—C6B—H6BB	109.4
C8A—N4A—C6A	114.11 (15)	N4B—C6B—C7B	111.11 (15)
N2A—C1A—N3A	122.85 (17)	H6BA—C6B—H6BB	108.0
N2A—C1A—C2A	116.04 (16)	C7B—C6B—H6BA	109.4
N3A—C1A—C2A	121.09 (15)	C7B—C6B—H6BB	109.4
C1A—C2A—H2AA	111.6	N1B—C7B—C6B	111.94 (14)
C1A—C2A—H2AB	111.6	N1B—C7B—H7BA	109.2
C1A—C2A—C3A	100.69 (14)	N1B—C7B—H7BB	109.2
H2AA—C2A—H2AB	109.4	C6B—C7B—H7BA	109.2
C3A—C2A—H2AA	111.6	C6B—C7B—H7BB	109.2
C3A—C2A—H2AB	111.6	H7BA—C7B—H7BB	107.9
N1A—C3A—H3AC	111.3	C9B—C8B—N4B	122.07 (16)
N1A—C3A—H3AD	111.3	C9B—C8B—C13B	117.59 (17)
C2A—C3A—N1A	102.33 (14)	C13B—C8B—N4B	120.29 (17)
C2A—C3A—H3AC	111.3	C8B—C9B—H9B	119.8
C2A—C3A—H3AD	111.3	C10B—C9B—C8B	120.44 (18)
H3AC—C3A—H3AD	109.2	C10B—C9B—H9B	119.8
N1A—C4A—H4AA	109.5	C9B—C10B—H10B	119.3
N1A—C4A—H4AB	109.5	C11B—C10B—C9B	121.40 (19)
N1A—C4A—C5A	110.69 (14)	C11B—C10B—H10B	119.3
H4AA—C4A—H4AB	108.1	C10B—C11B—H11B	120.8
C5A—C4A—H4AA	109.5	C10B—C11B—C12B	118.45 (19)
C5A—C4A—H4AB	109.5	C12B—C11B—H11B	120.8
N4A—C5A—C4A	109.40 (14)	C11B—C12B—H12B	119.5
N4A—C5A—H5AA	109.8	C13B—C12B—C11B	120.9 (2)
N4A—C5A—H5AB	109.8	C13B—C12B—H12B	119.5
C4A—C5A—H5AA	109.8	C8B—C13B—H13B	119.4
C4A—C5A—H5AB	109.8	C12B—C13B—C8B	121.2 (2)
H5AA—C5A—H5AB	108.2	C12B—C13B—H13B	119.4

3-(1H-1,3-benzimidazol-1-yl)-N'-{[(4-methylbenzene)sulfonyl]oxy}propanimidamide (10)

Crystal data

C17H18N4O3S	F(000) = 752
Mr = 358.41	Dx = 1.333 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.0524 (12) Å	Cell parameters from 3471 reflections
b = 19.127 (2) Å	θ = 2.2–25.1°
c = 8.8414 (10) Å	µ = 0.21 mm^−1
β = 107.131 (4)°	T = 120 K
V = 1786.1 (3) Å^3	Prism, colourless
Z = 4	0.33 × 0.16 × 0.12 mm

Data collection

Bruker APEX II Photon CCD detector diffractometer	3796 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
phi and ω scans	θmax = 30.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −15→15
Tmin = 0.699, Tmax = 0.746	k = −20→27
18771 measured reflections	l = −12→12
5403 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.018P)^2 + 0.4P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
5403 reflections	Δρmax = 0.32 e Å^−3
227 parameters	Δρmin = −0.56 e Å^−3
0 restraints

Special details

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. Single crystals were obtained from reaction mixtures. The intensities of reflections for the samples were measured with a Bruker Quest diffractometer using MoK_? radiation with multilayer optics (? = 0.71073Å)at 100.0 (2) (6, 7, 7·H₂O, 9, 10) or 295.0 (2) K (8a). The structures were solved by the direct method and refined by full-matrix least squares against F². Non-hydrogen atoms were refined anisotropically.

All calculations were made using the SHELXL ??(Sheldrick, 2015a)? and OLEX2 ??(Dolomanov et al., 2009)?] program packages. Experimental details and crystal parameters are listed in Table 1.

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

	x	y	z	Uiso*/Ueq
S1	0.87978 (3)	0.54882 (2)	0.66884 (4)	0.01927 (10)
O1	0.81067 (9)	0.52090 (5)	0.49557 (12)	0.0199 (2)
O2	0.79784 (10)	0.59401 (6)	0.72235 (13)	0.0250 (2)
O3	0.99582 (10)	0.57601 (6)	0.65191 (13)	0.0251 (2)
N1	0.67907 (11)	0.49769 (7)	0.48160 (15)	0.0194 (3)
N2	0.74128 (12)	0.40501 (8)	0.34614 (18)	0.0332 (4)
H2A	0.8194	0.4203	0.3648	0.040*
H2B	0.7176	0.3663	0.2916	0.040*
N3	0.53801 (11)	0.30460 (6)	0.52345 (14)	0.0186 (3)
N4	0.64588 (13)	0.20850 (7)	0.62803 (16)	0.0271 (3)
C1	0.90775 (14)	0.47259 (8)	0.78355 (17)	0.0210 (3)
C2	0.83193 (14)	0.45676 (9)	0.87948 (18)	0.0255 (3)
H2	0.7666	0.4878	0.8862	0.031*
C3	0.85304 (15)	0.39505 (9)	0.96501 (19)	0.0282 (4)
H3	0.8011	0.3839	1.0302	0.034*
C4	0.94855 (15)	0.34908 (9)	0.95760 (19)	0.0276 (4)
C5	1.02338 (16)	0.36665 (10)	0.8613 (2)	0.0326 (4)
H5	1.0895	0.3359	0.8557	0.039*
C6	1.00407 (15)	0.42746 (9)	0.7738 (2)	0.0290 (4)
H6	1.0556	0.4384	0.7079	0.035*
C7	0.97145 (19)	0.28269 (10)	1.0532 (2)	0.0406 (5)
H7A	1.0423	0.2895	1.1493	0.061*
H7B	0.9918	0.2448	0.9901	0.061*
H7C	0.8951	0.2705	1.0823	0.061*
C8	0.65908 (13)	0.44037 (8)	0.40026 (16)	0.0168 (3)
C9	0.52463 (13)	0.41426 (8)	0.36526 (17)	0.0182 (3)
H9A	0.5071	0.3813	0.2750	0.022*
H9B	0.4661	0.4544	0.3329	0.022*
C10	0.49769 (13)	0.37750 (8)	0.50573 (18)	0.0187 (3)
H10A	0.5415	0.4031	0.6040	0.022*
H10B	0.4056	0.3796	0.4924	0.022*
C11	0.63860 (14)	0.27683 (8)	0.63423 (18)	0.0234 (3)
H11	0.6986	0.3044	0.7097	0.028*
C12	0.47221 (14)	0.24900 (8)	0.43686 (18)	0.0191 (3)
C13	0.36041 (15)	0.24612 (9)	0.31158 (19)	0.0250 (3)
H13	0.3155	0.2871	0.2669	0.030*
C14	0.31895 (16)	0.18005 (9)	0.2563 (2)	0.0296 (4)
H14	0.2435	0.1755	0.1709	0.035*
C15	0.38529 (17)	0.11961 (9)	0.3230 (2)	0.0308 (4)
H15	0.3530	0.0752	0.2826	0.037*
C16	0.49607 (17)	0.12309 (9)	0.4458 (2)	0.0289 (4)
H16	0.5409	0.0819	0.4896	0.035*
C17	0.54035 (15)	0.18934 (8)	0.50366 (18)	0.0225 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01531 (16)	0.0210 (2)	0.02137 (18)	−0.00196 (14)	0.00522 (13)	−0.00340 (15)
O1	0.0164 (5)	0.0220 (6)	0.0210 (5)	−0.0041 (4)	0.0054 (4)	−0.0025 (4)
O2	0.0218 (5)	0.0246 (6)	0.0285 (6)	0.0014 (4)	0.0073 (5)	−0.0068 (5)
O3	0.0181 (5)	0.0268 (6)	0.0309 (6)	−0.0057 (4)	0.0080 (4)	−0.0034 (5)
N1	0.0121 (5)	0.0210 (7)	0.0250 (6)	−0.0018 (5)	0.0053 (5)	−0.0028 (5)
N2	0.0197 (6)	0.0347 (9)	0.0498 (9)	−0.0103 (6)	0.0173 (6)	−0.0244 (7)
N3	0.0177 (6)	0.0166 (7)	0.0222 (6)	−0.0003 (5)	0.0072 (5)	0.0020 (5)
N4	0.0295 (7)	0.0230 (8)	0.0285 (7)	0.0032 (6)	0.0079 (6)	0.0044 (6)
C1	0.0183 (7)	0.0242 (8)	0.0202 (7)	0.0001 (6)	0.0054 (6)	−0.0016 (6)
C2	0.0195 (7)	0.0331 (10)	0.0248 (8)	0.0016 (7)	0.0080 (6)	−0.0011 (7)
C3	0.0246 (8)	0.0382 (10)	0.0225 (8)	−0.0057 (7)	0.0081 (6)	0.0027 (7)
C4	0.0269 (8)	0.0283 (9)	0.0243 (8)	−0.0026 (7)	0.0024 (6)	0.0011 (7)
C5	0.0320 (9)	0.0313 (10)	0.0377 (10)	0.0089 (7)	0.0154 (8)	0.0049 (8)
C6	0.0277 (8)	0.0314 (10)	0.0329 (9)	0.0057 (7)	0.0166 (7)	0.0048 (7)
C7	0.0426 (11)	0.0349 (11)	0.0422 (11)	−0.0017 (9)	0.0094 (9)	0.0102 (9)
C8	0.0170 (6)	0.0168 (8)	0.0173 (7)	0.0003 (5)	0.0063 (5)	0.0019 (6)
C9	0.0163 (7)	0.0175 (8)	0.0213 (7)	0.0001 (5)	0.0065 (6)	0.0002 (6)
C10	0.0191 (7)	0.0162 (7)	0.0233 (7)	0.0004 (6)	0.0103 (6)	−0.0005 (6)
C11	0.0223 (7)	0.0225 (9)	0.0244 (8)	0.0009 (6)	0.0054 (6)	0.0024 (6)
C12	0.0209 (7)	0.0178 (8)	0.0219 (7)	−0.0020 (6)	0.0114 (6)	−0.0009 (6)
C13	0.0229 (7)	0.0276 (9)	0.0257 (8)	−0.0013 (6)	0.0091 (6)	−0.0015 (7)
C14	0.0283 (8)	0.0337 (10)	0.0283 (8)	−0.0075 (7)	0.0107 (7)	−0.0079 (7)
C15	0.0419 (10)	0.0265 (10)	0.0304 (9)	−0.0107 (7)	0.0206 (8)	−0.0101 (7)
C16	0.0423 (10)	0.0200 (9)	0.0309 (9)	0.0006 (7)	0.0212 (8)	−0.0002 (7)
C17	0.0275 (8)	0.0212 (8)	0.0225 (7)	0.0012 (6)	0.0129 (6)	0.0020 (6)

Geometric parameters (Å, º)

S1—O1	1.5894 (11)	C5—C6	1.378 (2)
S1—O2	1.4295 (11)	C6—H6	0.9500
S1—O3	1.4321 (11)	C7—H7A	0.9800
S1—C1	1.7508 (16)	C7—H7B	0.9800
O1—N1	1.4907 (15)	C7—H7C	0.9800
N1—C8	1.2941 (19)	C8—C9	1.5108 (19)
N2—H2A	0.8800	C9—H9A	0.9900
N2—H2B	0.8800	C9—H9B	0.9900
N2—C8	1.3296 (18)	C9—C10	1.5308 (19)
N3—C10	1.4582 (18)	C10—H10A	0.9900
N3—C11	1.3549 (19)	C10—H10B	0.9900
N3—C12	1.3849 (19)	C11—H11	0.9500
N4—C11	1.311 (2)	C12—C13	1.397 (2)
N4—C17	1.396 (2)	C12—C17	1.399 (2)
C1—C2	1.390 (2)	C13—H13	0.9500
C1—C6	1.393 (2)	C13—C14	1.383 (2)
C2—H2	0.9500	C14—H14	0.9500
C2—C3	1.384 (2)	C14—C15	1.402 (2)
C3—H3	0.9500	C15—H15	0.9500
C3—C4	1.390 (2)	C15—C16	1.378 (2)
C4—C5	1.392 (2)	C16—H16	0.9500
C4—C7	1.505 (2)	C16—C17	1.400 (2)
C5—H5	0.9500
O1—S1—C1	103.37 (7)	H7B—C7—H7C	109.5
O2—S1—O1	110.53 (6)	N1—C8—N2	127.46 (13)
O2—S1—O3	119.29 (7)	N1—C8—C9	112.99 (12)
O2—S1—C1	109.44 (7)	N2—C8—C9	119.55 (13)
O3—S1—O1	102.25 (6)	C8—C9—H9A	108.8
O3—S1—C1	110.62 (7)	C8—C9—H9B	108.8
N1—O1—S1	111.10 (8)	C8—C9—C10	113.60 (12)
C8—N1—O1	107.52 (11)	H9A—C9—H9B	107.7
H2A—N2—H2B	120.0	C10—C9—H9A	108.8
C8—N2—H2A	120.0	C10—C9—H9B	108.8
C8—N2—H2B	120.0	N3—C10—C9	113.58 (12)
C11—N3—C10	127.75 (13)	N3—C10—H10A	108.8
C11—N3—C12	106.50 (13)	N3—C10—H10B	108.8
C12—N3—C10	125.51 (12)	C9—C10—H10A	108.8
C11—N4—C17	104.31 (13)	C9—C10—H10B	108.8
C2—C1—S1	119.97 (12)	H10A—C10—H10B	107.7
C2—C1—C6	120.79 (15)	N3—C11—H11	123.0
C6—C1—S1	119.21 (12)	N4—C11—N3	114.07 (14)
C1—C2—H2	120.5	N4—C11—H11	123.0
C3—C2—C1	118.97 (15)	N3—C12—C13	131.80 (15)
C3—C2—H2	120.5	N3—C12—C17	105.26 (13)
C2—C3—H3	119.3	C13—C12—C17	122.91 (15)
C2—C3—C4	121.45 (15)	C12—C13—H13	122.0
C4—C3—H3	119.3	C14—C13—C12	116.08 (16)
C3—C4—C5	118.19 (16)	C14—C13—H13	122.0
C3—C4—C7	120.78 (15)	C13—C14—H14	119.1
C5—C4—C7	121.03 (16)	C13—C14—C15	121.79 (16)
C4—C5—H5	119.1	C15—C14—H14	119.1
C6—C5—C4	121.70 (16)	C14—C15—H15	119.2
C6—C5—H5	119.1	C16—C15—C14	121.65 (16)
C1—C6—H6	120.6	C16—C15—H15	119.2
C5—C6—C1	118.89 (15)	C15—C16—H16	121.1
C5—C6—H6	120.6	C15—C16—C17	117.74 (16)
C4—C7—H7A	109.5	C17—C16—H16	121.1
C4—C7—H7B	109.5	N4—C17—C12	109.85 (14)
C4—C7—H7C	109.5	N4—C17—C16	130.29 (15)
H7A—C7—H7B	109.5	C12—C17—C16	119.83 (15)
H7A—C7—H7C	109.5