Structures of artificial sweeteners – cyclamic acid and sodium cyclamate with other cyclamates

In the course of a study on artificial sweeteners, new crystal structures of cyclamic acid, sodium cyclamate, potassium cyclamate, ammonium cyclamate, rubidium cyclamate and tetra-n-propylammonium cyclamate have been determined. Cyclamic acid exists in its zwitterionic form in the crystalline state. The zwitterions are connected through hydrogen bonds of the N—H...O type to form two-dimensional sheets. The sodium, potassium, ammonium and rubidium cyclamates are isostructural, with the cyclamate moieties linked through hydrogen bonds into linear chains. Taking into account the connectivity through cations, two-dimensional layers with a hydrophobic surface are constructed. In tetra(n-propyl)ammonium cyclamate the large, non-coordinating cation apparently prevents the formation of chains and thereby facilitates the centrosymmetric head-to-head discrete dimeric arrangement of the cyclamate moieties.

Computing details

For all compounds, data collection: COLLECT (Hooft, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS86 (Sheldrick, 1986); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1971), PLUTON (Spek, 1991), PLATON (Spek, 1998 and Farrugia, 2000), ORTEP-3 (Farrugia, 1999), Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997), PARST (Nardelli, 1983 and 1995), WinGX (Farrugia, 1999).

Figures

(I) N-Cyclohexylsulfamic acid

Crystal data

C6H13NO3S	F(000) = 384
Mr = 179.23	Dx = 1.401 Mg m^−3
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 2178 reflections
a = 8.1711 (10) Å	θ = 1–28.7°
b = 10.9972 (12) Å	µ = 0.34 mm^−1
c = 9.4601 (11) Å	T = 150 K
β = 91.575 (5)°	Plate, colourless
V = 849.72 (17) Å^3	0.24 × 0.24 × 0.07 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	2195 independent reflections
Radiation source: fine-focus sealed tube	1955 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Detector resolution: 0.055 pixels mm^-1	θmax = 28.7°, θmin = 1.9°
ω scans at κ=55°	h = −11→11
Absorption correction: multi-scan DENZO and SCALEPACK (Otwinowski & Minor, 1997) based on the redundancy of symmetry-related measurements	k = −14→14
Tmin = 0.928, Tmax = 0.980	l = −12→12
10483 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0224P)^2 + 0.7859P] where P = (Fo^2 + 2Fc^2)/3
2195 reflections	(Δ/σ)max < 0.001
108 parameters	Δρmax = 0.47 e Å^−3
0 restraints	Δρmin = −0.41 e Å^−3

Special details

Experimental. KappaCCD Nonius diffractometer. 214 frames in 7 sets of ω and ϕ scans at κ = 55°. Rotation/frame=2°. Crystal-detector distance=35.0 mm. Measuring time=100 s/frame. Mosaicity=0.407 (2)°.

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
S	0.24414 (4)	−0.07026 (4)	0.04790 (4)	0.01531 (12)
O1	0.21918 (15)	−0.16708 (11)	−0.05112 (13)	0.0236 (3)
O2	0.40087 (13)	−0.06753 (12)	0.12219 (12)	0.0224 (3)
O3	0.10846 (13)	−0.04143 (11)	0.13603 (12)	0.0193 (3)
N	0.25497 (16)	0.05978 (12)	−0.06708 (14)	0.0149 (3)
C1	0.21238 (18)	0.18190 (14)	−0.00475 (17)	0.0170 (3)
H1A	0.0996	0.1766	0.0333	0.020*
C2	0.3294 (2)	0.21897 (17)	0.11543 (19)	0.0247 (4)
H2A	0.4422	0.2249	0.0805	0.030*
H2E	0.3283	0.1571	0.1914	0.030*
C3	0.2756 (2)	0.34187 (18)	0.1732 (2)	0.0294 (4)
H3A	0.1659	0.3336	0.2142	0.035*
H3E	0.3532	0.3678	0.2496	0.035*
C4	0.2693 (3)	0.43840 (17)	0.0578 (2)	0.0352 (5)
H4A	0.3808	0.4523	0.0228	0.042*
H4E	0.2292	0.5159	0.0973	0.042*
C5	0.1559 (3)	0.39843 (18)	−0.0648 (2)	0.0360 (5)
H5A	0.1574	0.4604	−0.1407	0.043*
H5E	0.0424	0.3919	−0.0316	0.043*
C6	0.2101 (2)	0.27523 (17)	−0.12392 (19)	0.0281 (4)
H6A	0.1332	0.2490	−0.2007	0.034*
H6E	0.3206	0.2825	−0.1634	0.034*
H	0.359 (3)	0.0613 (18)	−0.098 (2)	0.024 (5)*
H1	0.193 (3)	0.0440 (19)	−0.135 (2)	0.025 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.01325 (18)	0.0214 (2)	0.01125 (18)	0.00033 (13)	0.00071 (12)	0.00195 (14)
O1	0.0315 (6)	0.0214 (6)	0.0179 (6)	−0.0006 (5)	0.0009 (5)	−0.0014 (5)
O2	0.0130 (5)	0.0359 (7)	0.0183 (6)	0.0016 (5)	−0.0008 (4)	0.0073 (5)
O3	0.0135 (5)	0.0301 (6)	0.0145 (5)	0.0000 (4)	0.0030 (4)	0.0030 (4)
N	0.0127 (6)	0.0218 (7)	0.0100 (6)	0.0001 (5)	0.0003 (5)	0.0002 (5)
C1	0.0153 (6)	0.0194 (7)	0.0164 (7)	0.0005 (5)	0.0011 (5)	−0.0009 (6)
C2	0.0231 (8)	0.0294 (9)	0.0213 (8)	0.0025 (7)	−0.0049 (6)	−0.0057 (7)
C3	0.0303 (9)	0.0308 (10)	0.0270 (9)	0.0007 (7)	−0.0047 (7)	−0.0107 (7)
C4	0.0432 (11)	0.0228 (9)	0.0399 (11)	−0.0063 (8)	0.0057 (9)	−0.0066 (8)
C5	0.0573 (13)	0.0221 (9)	0.0283 (10)	0.0052 (9)	−0.0016 (9)	0.0027 (7)
C6	0.0415 (10)	0.0239 (9)	0.0187 (8)	0.0008 (7)	−0.0001 (7)	0.0019 (7)

Geometric parameters (Å, º)

S—O1	1.4290 (12)	C2—H2E	0.9900
S—O3	1.4407 (11)	C3—C4	1.523 (3)
S—O2	1.4441 (11)	C3—H3A	0.9900
S—N	1.8003 (14)	C3—H3E	0.9900
N—C1	1.511 (2)	C4—C5	1.529 (3)
N—H	0.91 (2)	C4—H4A	0.9900
N—H1	0.83 (2)	C4—H4E	0.9900
C1—C2	1.521 (2)	C5—C6	1.536 (3)
C1—C6	1.524 (2)	C5—H5A	0.9900
C1—H1A	1.0000	C5—H5E	0.9900
C2—C3	1.527 (3)	C6—H6A	0.9900
C2—H2A	0.9900	C6—H6E	0.9900
O1—S—O3	116.43 (7)	C4—C3—C2	111.39 (16)
O1—S—O2	116.30 (8)	C4—C3—H3A	109.4
O3—S—O2	113.58 (7)	C2—C3—H3A	109.4
O1—S—N	101.79 (7)	C4—C3—H3E	109.4
O3—S—N	103.08 (7)	C2—C3—H3E	109.4
O2—S—N	102.70 (7)	H3A—C3—H3E	108.0
C1—N—S	117.03 (10)	C3—C4—C5	110.57 (16)
C1—N—H	109.6 (13)	C3—C4—H4A	109.5
S—N—H	105.6 (13)	C5—C4—H4A	109.5
C1—N—H1	110.2 (15)	C3—C4—H4E	109.5
S—N—H1	105.2 (15)	C5—C4—H4E	109.5
H—N—H1	108.7 (19)	H4A—C4—H4E	108.1
N—C1—C2	112.53 (13)	C4—C5—C6	110.83 (17)
N—C1—C6	107.94 (13)	C4—C5—H5A	109.5
C2—C1—C6	111.54 (14)	C6—C5—H5A	109.5
N—C1—H1A	108.2	C4—C5—H5E	109.5
C2—C1—H1A	108.2	C6—C5—H5E	109.5
C6—C1—H1A	108.2	H5A—C5—H5E	108.1
C1—C2—C3	108.90 (14)	C1—C6—C5	108.81 (15)
C1—C2—H2A	109.9	C1—C6—H6A	109.9
C3—C2—H2A	109.9	C5—C6—H6A	109.9
C1—C2—H2E	109.9	C1—C6—H6E	109.9
C3—C2—H2E	109.9	C5—C6—H6E	109.9
H2A—C2—H2E	108.3	H6A—C6—H6E	108.3
O1—S—N—C1	155.71 (11)	C2—C1—C6—C5	−59.6 (2)
O3—S—N—C1	34.70 (12)	C4—C5—C6—C1	57.4 (2)
O2—S—N—C1	−83.55 (11)	H1A—C1—N—H	−176.6
S—N—C1—C2	63.07 (15)	H1A—C1—N—H1	63.7
S—N—C1—C6	−173.41 (11)	C2—C1—N—S	63.07 (15)
N—C1—C2—C3	−179.10 (14)	H—N—S—O1	−82.0 (14)
C6—C1—C2—C3	59.41 (19)	H—N—S—O2	38.7 (14)
C1—C2—C3—C4	−57.3 (2)	H—N—S—O3	157.0 (14)
C2—C3—C4—C5	56.6 (2)	H1—N—S—O1	32.9 (15)
C3—C4—C5—C6	−56.5 (2)	H1—N—S—O2	153.7 (15)
N—C1—C6—C5	176.30 (14)	H1—N—S—O3	−88.1 (15)

(II) Sodium N-cyclohexylsulfamate

Crystal data

Na^+·C6H12NSO3^−	F(000) = 848
Mr = 201.22	Dx = 1.605 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1114 reflections
a = 31.083 (6) Å	θ = 1–27.9°
b = 6.2718 (14) Å	µ = 0.40 mm^−1
c = 8.5682 (17) Å	T = 150 K
β = 94.481 (10)°	Plate, colourless
V = 1665.3 (6) Å^3	0.20 × 0.18 × 0.08 mm
Z = 8

Data collection

Nonius KappaCCD diffractometer	1923 independent reflections
Radiation source: fine-focus sealed tube	1480 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
Detector resolution: 0.055 pixels mm^-1	θmax = 27.7°, θmin = 1.3°
ω scans at κ = 55°	h = −40→40
Absorption correction: multi-scan DENZO and SCALEPACK (Otwinowski & Minor, 1997) based on the redundancy of symmetry-related measurements	k = −8→8
Tmin = 0.928, Tmax = 0.961	l = −11→10
10594 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0356P)^2 + 6.6274P] where P = (Fo^2 + 2Fc^2)/3
1923 reflections	(Δ/σ)max < 0.001
113 parameters	Δρmax = 0.70 e Å^−3
0 restraints	Δρmin = −0.56 e Å^−3

Special details

Experimental. KappaCCD Nonius diffractometer. 1152 frames in 5 sets of ω and ϕ scans at κ = 55°. Rotation/frame=0.3°. Crystal-detector distance=28.0 mm. Measuring time=30 s/frame. Mosaicity=0.542 (4)°.

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
Na	0.23231 (4)	0.62743 (18)	0.18626 (13)	0.0207 (3)
S	0.19481 (2)	0.12150 (11)	0.03258 (8)	0.0166 (2)
O1	0.20935 (6)	0.2810 (3)	0.1485 (2)	0.0206 (5)
O2	0.22509 (6)	−0.0589 (3)	0.0390 (2)	0.0216 (5)
O3	0.18643 (6)	0.2011 (3)	−0.1255 (2)	0.0203 (5)
N	0.14785 (7)	0.0461 (4)	0.0890 (3)	0.0182 (5)
C1	0.11847 (9)	−0.0859 (4)	−0.0149 (3)	0.0180 (6)
H1A	0.1159	−0.0173	−0.1206	0.022*
C2	0.13362 (9)	−0.3161 (5)	−0.0352 (4)	0.0214 (6)
H2A	0.1615	−0.3160	−0.0835	0.026*
H2E	0.1381	−0.3852	0.0687	0.026*
C3	0.10038 (10)	−0.4426 (5)	−0.1382 (4)	0.0278 (7)
H3A	0.1100	−0.5928	−0.1435	0.033*
H3E	0.0987	−0.3837	−0.2457	0.033*
C4	0.05540 (10)	−0.4361 (5)	−0.0767 (4)	0.0277 (7)
H4A	0.0345	−0.5099	−0.1515	0.033*
H4E	0.0560	−0.5120	0.0247	0.033*
C5	0.04077 (9)	−0.2064 (5)	−0.0551 (4)	0.0246 (7)
H5A	0.0127	−0.2060	−0.0076	0.030*
H5E	0.0366	−0.1360	−0.1586	0.030*
C6	0.07391 (9)	−0.0816 (5)	0.0495 (4)	0.0219 (6)
H6A	0.0760	−0.1437	0.1560	0.026*
H6E	0.0642	0.0681	0.0574	0.026*
H	0.1531 (11)	−0.020 (6)	0.188 (4)	0.029 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Na	0.0278 (6)	0.0117 (6)	0.0226 (6)	−0.0007 (4)	0.0012 (5)	−0.0015 (5)
S	0.0220 (4)	0.0107 (3)	0.0171 (4)	−0.0004 (3)	0.0018 (2)	0.0002 (3)
O1	0.0279 (11)	0.0145 (10)	0.0191 (10)	−0.0032 (8)	−0.0009 (8)	−0.0031 (8)
O2	0.0254 (10)	0.0137 (10)	0.0264 (11)	0.0033 (8)	0.0055 (8)	0.0025 (9)
O3	0.0272 (11)	0.0165 (10)	0.0170 (10)	−0.0021 (8)	0.0005 (8)	0.0020 (9)
N	0.0202 (12)	0.0150 (12)	0.0195 (13)	−0.0015 (10)	0.0019 (9)	−0.0030 (10)
C1	0.0224 (14)	0.0149 (13)	0.0166 (14)	−0.0036 (11)	0.0006 (10)	0.0003 (12)
C2	0.0239 (15)	0.0140 (13)	0.0265 (16)	0.0011 (11)	0.0036 (12)	−0.0031 (12)
C3	0.0302 (16)	0.0195 (16)	0.0332 (18)	−0.0029 (13)	−0.0008 (13)	−0.0038 (14)
C4	0.0300 (16)	0.0211 (16)	0.0310 (17)	−0.0059 (13)	−0.0049 (13)	−0.0024 (14)
C5	0.0208 (15)	0.0224 (16)	0.0303 (17)	−0.0013 (12)	0.0001 (12)	0.0010 (14)
C6	0.0230 (15)	0.0175 (15)	0.0253 (16)	0.0004 (11)	0.0026 (12)	−0.0013 (12)

Geometric parameters (Å, º)

Na—O1	2.302 (2)	C1—H1A	1.0000
Na—O1^i	2.412 (2)	C2—C3	1.528 (4)
Na—O2^ii	2.462 (2)	C2—H2A	0.9900
Na—O2^i	2.859 (2)	C2—H2E	0.9900
Na—S^i	3.1756 (14)	C3—C4	1.533 (5)
Na—Na^i	3.4712 (12)	C3—H3A	0.9900
S—O3	1.448 (2)	C3—H3E	0.9900
S—O1	1.457 (2)	C4—C5	1.526 (5)
S—O2	1.470 (2)	C4—H4A	0.9900
S—N	1.643 (2)	C4—H4E	0.9900
O2—Na^ii	2.462 (2)	C5—C6	1.528 (4)
N—C1	1.478 (4)	C5—H5A	0.9900
N—H	0.95 (4)	C5—H5E	0.9900
C1—C6	1.531 (4)	C6—H6A	0.9900
C1—C2	1.532 (4)	C6—H6E	0.9900
O1—Na—O1^i	132.07 (8)	C2—C1—H1A	107.9
O1—Na—O2^ii	84.56 (8)	C3—C2—C1	110.8 (2)
O1^i—Na—O2^ii	95.97 (8)	C3—C2—H2A	109.5
O1—Na—O2^i	81.27 (7)	C1—C2—H2A	109.5
O1^i—Na—O2^i	53.24 (7)	C3—C2—H2E	109.5
O2^ii—Na—O2^i	109.34 (7)	C1—C2—H2E	109.5
O1—Na—S^i	106.89 (6)	H2A—C2—H2E	108.1
O1^i—Na—S^i	25.91 (5)	C2—C3—C4	112.4 (3)
O2^ii—Na—S^i	101.37 (6)	C2—C3—H3A	109.1
O2^i—Na—S^i	27.57 (4)	C4—C3—H3A	109.1
O1—Na—Na^i	169.76 (8)	C2—C3—H3E	109.1
O1^i—Na—Na^i	41.35 (6)	C4—C3—H3E	109.1
O2^ii—Na—Na^i	103.16 (7)	H3A—C3—H3E	107.9
O2^i—Na—Na^i	89.73 (6)	C5—C4—C3	110.8 (3)
S^i—Na—Na^i	65.30 (4)	C5—C4—H4A	109.5
O3—S—O1	115.13 (12)	C3—C4—H4A	109.5
O3—S—O2	111.62 (12)	C5—C4—H4E	109.5
O1—S—O2	109.85 (12)	C3—C4—H4E	109.5
O3—S—N	106.00 (12)	H4A—C4—H4E	108.1
O1—S—N	103.44 (12)	C4—C5—C6	111.2 (3)
O2—S—N	110.38 (12)	C4—C5—H5A	109.4
S—O1—Na	145.12 (13)	C6—C5—H5A	109.4
S—O2—Na^ii	119.12 (12)	C4—C5—H5E	109.4
C1—N—S	120.35 (19)	C6—C5—H5E	109.4
C1—N—H	111 (2)	H5A—C5—H5E	108.0
S—N—H	107 (2)	C5—C6—C1	111.5 (2)
N—C1—C6	107.8 (2)	C5—C6—H6A	109.3
N—C1—C2	114.5 (2)	C1—C6—H6A	109.3
C6—C1—C2	110.6 (2)	C5—C6—H6E	109.3
N—C1—H1A	107.9	C1—C6—H6E	109.3
C6—C1—H1A	107.9	H6A—C6—H6E	108.0
O3—S—N—C1	46.9 (2)	C4—C5—C6—C1	56.4 (3)
O1—S—N—C1	168.4 (2)	N—C1—C6—C5	177.5 (2)
O2—S—N—C1	−74.2 (2)	C2—C1—C6—C5	−56.6 (3)
S—N—C1—C6	−165.7 (2)	H1A—C1—N—H	−175.1
N—C1—C2—C3	177.5 (2)	C2—C1—N—S	70.7 (3)
C6—C1—C2—C3	55.4 (3)	H—N—S—O1	−64 (2)
C1—C2—C3—C4	−55.0 (4)	H—N—S—O2	53 (2)
C2—C3—C4—C5	54.6 (4)	H—N—S—O3	174 (2)
C3—C4—C5—C6	−54.7 (4)

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

(III) Potassium N-cyclohexylsulfamate

Crystal data

K^+·C6H12NSO3^−	F(000) = 912
Mr = 217.33	Dx = 1.598 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2252 reflections
a = 33.656 (8) Å	θ = 1–27.5°
b = 6.274 (3) Å	µ = 0.79 mm^−1
c = 8.572 (4) Å	T = 150 K
β = 93.35 (1)°	Prism, colourless
V = 1807.0 (13) Å^3	0.13 × 0.13 × 0.12 mm
Z = 8

Data collection

Nonius KappaCCD diffractometer	1953 independent reflections
Radiation source: fine-focus sealed tube	1565 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
Detector resolution: 0.055 pixels mm^-1	θmax = 27.4°, θmin = 3.3°
ω scans at κ = 55°	h = −43→43
Absorption correction: multi-scan DENZO and SCALEPACK (Otwinowski & Minor, 1997) based on the redundancy of symmetry-related measurements	k = −8→8
Tmin = 0.905, Tmax = 0.911	l = −11→10
75861 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0303P)^2 + 3.2501P] where P = (Fo^2 + 2Fc^2)/3
1953 reflections	(Δ/σ)max = 0.001
113 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.44 e Å^−3

Special details

Experimental. KappaCCD Nonius diffractometer. 569 frames in 6 sets of ω and ϕ scans at κ = 55°. Rotation/frame=0.7°. Crystal-detector distance=30.50 mm. Measuring time=126 s/frame. Mosaicity=0.748 (4)°.

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
K	0.718720 (14)	0.56650 (8)	0.89036 (6)	0.02105 (15)
S	0.691677 (15)	0.07921 (9)	0.77736 (6)	0.01853 (16)
O1	0.73023 (5)	0.0564 (3)	0.86271 (19)	0.0252 (4)
O2	0.67405 (5)	−0.1265 (3)	0.73404 (18)	0.0238 (4)
O3	0.69331 (5)	0.2208 (3)	0.64353 (18)	0.0268 (4)
N	0.66446 (5)	0.2061 (3)	0.9001 (2)	0.0194 (4)
C1	0.62172 (6)	0.2413 (4)	0.8574 (3)	0.0209 (5)
H1A	0.6188	0.2759	0.7435	0.025*
C2	0.59561 (7)	0.0477 (4)	0.8878 (3)	0.0257 (5)
H2A	0.5993	0.0058	0.9990	0.031*
H2E	0.6038	−0.0737	0.8233	0.031*
C3	0.55151 (7)	0.0982 (4)	0.8481 (3)	0.0300 (6)
H3A	0.5474	0.1272	0.7348	0.036*
H3E	0.5351	−0.0271	0.8728	0.036*
C4	0.53800 (7)	0.2907 (4)	0.9398 (3)	0.0303 (6)
H4A	0.5100	0.3251	0.9070	0.036*
H4E	0.5392	0.2560	1.0527	0.036*
C5	0.56428 (7)	0.4834 (4)	0.9124 (3)	0.0317 (6)
H5A	0.5562	0.6027	0.9793	0.038*
H5E	0.5603	0.5291	0.8021	0.038*
C6	0.60829 (7)	0.4348 (4)	0.9488 (3)	0.0269 (5)
H6A	0.6129	0.4075	1.0621	0.032*
H6E	0.6244	0.5603	0.9220	0.032*
H	0.6679 (7)	0.161 (4)	0.980 (3)	0.009 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
K	0.0235 (3)	0.0204 (3)	0.0192 (3)	−0.00059 (19)	0.00129 (18)	−0.0020 (2)
S	0.0208 (3)	0.0201 (3)	0.0148 (3)	0.0004 (2)	0.0012 (2)	0.0007 (2)
O1	0.0201 (8)	0.0350 (11)	0.0202 (8)	0.0020 (7)	−0.0002 (6)	−0.0015 (7)
O2	0.0294 (8)	0.0215 (9)	0.0206 (8)	−0.0019 (7)	0.0014 (7)	−0.0030 (7)
O3	0.0336 (9)	0.0277 (10)	0.0196 (8)	0.0003 (8)	0.0066 (7)	0.0064 (7)
N	0.0239 (10)	0.0221 (11)	0.0120 (9)	0.0017 (8)	0.0004 (7)	0.0006 (8)
C1	0.0212 (10)	0.0225 (13)	0.0192 (11)	0.0012 (9)	0.0011 (8)	0.0008 (10)
C2	0.0247 (11)	0.0202 (13)	0.0323 (13)	0.0000 (10)	0.0034 (10)	0.0019 (11)
C3	0.0235 (11)	0.0279 (15)	0.0387 (15)	−0.0020 (10)	0.0023 (10)	−0.0030 (12)
C4	0.0215 (11)	0.0309 (14)	0.0390 (14)	0.0020 (10)	0.0057 (10)	−0.0017 (12)
C5	0.0272 (12)	0.0284 (14)	0.0402 (15)	0.0064 (11)	0.0077 (11)	−0.0021 (12)
C6	0.0264 (12)	0.0226 (13)	0.0323 (13)	−0.0018 (10)	0.0057 (10)	−0.0061 (11)

Geometric parameters (Å, º)

K—N	2.911 (2)	C2—H2A	0.9900
K—O3	3.115 (2)	C2—H2E	0.9900
K—O1	3.234 (2)	C3—C4	1.525 (4)
K—S	3.3182 (16)	C3—H3A	0.9900
S—O3	1.4544 (18)	C3—H3E	0.9900
S—O1	1.4588 (16)	C4—C5	1.524 (4)
S—O2	1.4592 (18)	C4—H4A	0.9900
S—N	1.641 (2)	C4—H4E	0.9900
N—C1	1.480 (3)	C5—C6	1.526 (3)
N—H	0.75 (3)	C5—H5A	0.9900
C1—C6	1.527 (3)	C5—H5E	0.9900
C1—C2	1.530 (3)	C6—H6A	0.9900
C1—H1A	1.0000	C6—H6E	0.9900
C2—C3	1.536 (3)
N—K—O3	47.99 (5)	C1—C2—H2A	109.5
N—K—O1	46.48 (5)	C3—C2—H2A	109.5
O3—K—O1	44.80 (5)	C1—C2—H2E	109.5
N—K—S	29.63 (4)	C3—C2—H2E	109.5
O3—K—S	25.89 (3)	H2A—C2—H2E	108.1
O1—K—S	25.69 (3)	C4—C3—C2	111.3 (2)
O3—S—O1	112.46 (10)	C4—C3—H3A	109.4
O3—S—O2	111.89 (10)	C2—C3—H3A	109.4
O1—S—O2	112.16 (10)	C4—C3—H3E	109.4
O3—S—N	104.94 (11)	C2—C3—H3E	109.4
O1—S—N	103.85 (10)	H3A—C3—H3E	108.0
O2—S—N	110.99 (10)	C5—C4—C3	110.8 (2)
O3—S—K	69.22 (8)	C5—C4—H4A	109.5
O1—S—K	73.94 (7)	C3—C4—H4A	109.5
O2—S—K	171.72 (7)	C5—C4—H4E	109.5
N—S—K	61.30 (8)	C3—C4—H4E	109.5
C1—N—S	119.01 (16)	H4A—C4—H4E	108.1
C1—N—K	118.63 (15)	C4—C5—C6	112.0 (2)
S—N—K	89.07 (8)	C4—C5—H5A	109.2
C1—N—H	112.4 (18)	C6—C5—H5A	109.2
S—N—H	110.1 (18)	C4—C5—H5E	109.2
K—N—H	104.9 (19)	C6—C5—H5E	109.2
N—C1—C6	107.73 (18)	H5A—C5—H5E	107.9
N—C1—C2	113.5 (2)	C5—C6—C1	111.5 (2)
C6—C1—C2	110.72 (19)	C5—C6—H6A	109.3
N—C1—H1A	108.2	C1—C6—H6A	109.3
C6—C1—H1A	108.2	C5—C6—H6E	109.3
C2—C1—H1A	108.2	C1—C6—H6E	109.3
C1—C2—C3	110.8 (2)	H6A—C6—H6E	108.0
O3—S—N—C1	67.0 (2)	C3—C4—C5—C6	−54.6 (3)
O1—S—N—C1	−174.77 (17)	C4—C5—C6—C1	54.8 (3)
O2—S—N—C1	−54.1 (2)	N—C1—C6—C5	−179.9 (2)
S—N—C1—C6	−155.78 (17)	C2—C1—C6—C5	−55.2 (3)
K—N—C1—C6	−49.4 (2)	H1A—C1—N—H	−169.8
S—N—C1—C2	81.3 (2)	C2—C1—N—S	81.3 (2)
N—C1—C2—C3	177.42 (19)	H—N—S—O1	−43 (2)
C6—C1—C2—C3	56.1 (3)	H—N—S—O2	78 (2)
C1—C2—C3—C4	−56.7 (3)	H—N—S—O3	−161 (2)
C2—C3—C4—C5	55.5 (3)

(IV) Ammonium N-cyclohexylsulfamate

Crystal data

NH4^+·C6H12NSO3^−	F(000) = 848
Mr = 196.27	Dx = 1.371 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3373 reflections
a = 33.6671 (19) Å	θ = 1–26.4°
b = 6.4571 (12) Å	µ = 0.32 mm^−1
c = 8.7572 (15) Å	T = 150 K
β = 92.961 (2)°	Plate, colourless
V = 1901.1 (5) Å^3	0.29 × 0.24 × 0.10 mm
Z = 8

Data collection

Nonius KappaCCD diffractometer	1936 independent reflections
Radiation source: fine-focus sealed tube	1650 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
Detector resolution: 0.055 pixels mm^-1	θmax = 26.4°, θmin = 3.6°
ω scans at κ = 55°	h = 0→41
Absorption correction: multi-scan DENZO and SCALEPACK (Otwinowski & Minor, 1997) based on the redundancy of symmetry-related measurements	k = 0→8
Tmin = 0.905, Tmax = 0.975	l = −10→10
24925 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.20	w = 1/[σ^2(Fo^2) + (0.0148P)^2 + 3.707P] where P = (Fo^2 + 2Fc^2)/3
1936 reflections	(Δ/σ)max < 0.001
126 parameters	Δρmax = 0.19 e Å^−3
4 restraints	Δρmin = −0.35 e Å^−3

Special details

Experimental. KappaCCD Nonius diffractometer. 261 frames in 5 sets of ω and ϕ scans at κ = 55°. Rotation/frame=1.4°. Crystal-detector distance=30.00 mm. Measuring time=280 s/frame. Mosaicity=0.974 (3)°.

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
N1	0.21782 (6)	1.0435 (3)	0.9118 (2)	0.0239 (4)
S	0.187535 (15)	0.55625 (8)	0.76335 (6)	0.01930 (16)
O1	0.22766 (4)	0.5492 (3)	0.83511 (17)	0.0262 (4)
O2	0.17078 (5)	0.3513 (2)	0.73872 (18)	0.0285 (4)
O3	0.18506 (5)	0.6804 (3)	0.62562 (17)	0.0296 (4)
N	0.16239 (5)	0.6885 (3)	0.8884 (2)	0.0184 (4)
C1	0.11965 (6)	0.7285 (3)	0.8514 (2)	0.0205 (5)
H1A	0.1161	0.7570	0.7393	0.025*
C2	0.09313 (6)	0.5458 (4)	0.8893 (3)	0.0268 (5)
H2A	0.0975	0.5099	0.9988	0.032*
H2E	0.1004	0.4239	0.8282	0.032*
C3	0.04923 (7)	0.5976 (4)	0.8554 (3)	0.0337 (6)
H3A	0.0444	0.6191	0.7441	0.040*
H3E	0.0327	0.4795	0.8861	0.040*
C4	0.03710 (7)	0.7912 (4)	0.9404 (3)	0.0335 (6)
H4E	0.0091	0.8260	0.9106	0.040*
H4A	0.0389	0.7643	1.0518	0.040*
C5	0.06374 (7)	0.9731 (4)	0.9043 (3)	0.0342 (6)
H5E	0.0564	1.0942	0.9662	0.041*
H5A	0.0594	1.0105	0.7950	0.041*
C6	0.10785 (7)	0.9225 (4)	0.9376 (3)	0.0293 (5)
H6E	0.1243	1.0408	0.9065	0.035*
H6A	0.1129	0.9007	1.0488	0.035*
H11	0.2050 (9)	1.142 (5)	0.934 (4)	0.053 (4)*
H12	0.2361 (9)	1.010 (5)	0.992 (3)	0.053 (4)*
H13	0.2001 (9)	0.932 (5)	0.907 (3)	0.053 (4)*
H14	0.2309 (9)	1.051 (5)	0.828 (3)	0.053 (4)*
H	0.1664 (7)	0.633 (4)	0.974 (3)	0.027 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0211 (10)	0.0217 (10)	0.0291 (10)	0.0009 (8)	0.0036 (8)	−0.0026 (9)
S	0.0182 (3)	0.0231 (3)	0.0165 (3)	0.0015 (2)	0.00085 (19)	−0.0002 (2)
O1	0.0154 (8)	0.0406 (10)	0.0226 (8)	0.0047 (7)	0.0000 (6)	−0.0034 (7)
O2	0.0305 (9)	0.0219 (8)	0.0330 (9)	−0.0005 (7)	0.0015 (7)	−0.0050 (7)
O3	0.0350 (9)	0.0366 (10)	0.0177 (7)	0.0043 (8)	0.0057 (7)	0.0074 (7)
N	0.0167 (9)	0.0226 (10)	0.0157 (9)	0.0017 (7)	−0.0005 (7)	0.0009 (8)
C1	0.0168 (11)	0.0227 (11)	0.0217 (10)	0.0018 (9)	−0.0014 (8)	0.0015 (9)
C2	0.0191 (11)	0.0220 (12)	0.0392 (13)	−0.0004 (9)	0.0000 (9)	0.0007 (11)
C3	0.0174 (12)	0.0323 (14)	0.0516 (15)	−0.0022 (10)	0.0037 (11)	−0.0044 (12)
C4	0.0209 (12)	0.0366 (14)	0.0434 (14)	0.0018 (10)	0.0050 (11)	−0.0021 (12)
C5	0.0259 (13)	0.0277 (13)	0.0494 (15)	0.0079 (10)	0.0064 (11)	−0.0021 (12)
C6	0.0225 (12)	0.0238 (12)	0.0420 (14)	0.0014 (10)	0.0057 (10)	−0.0038 (11)

Geometric parameters (Å, º)

N1—H11	0.80 (3)	C2—H2A	0.9900
N1—H12	0.93 (3)	C2—H2E	0.9900
N1—H13	0.93 (3)	C3—C4	1.522 (3)
N1—H14	0.88 (3)	C3—H3A	0.9900
S—O3	1.4472 (16)	C3—H3E	0.9900
S—O2	1.4504 (17)	C4—C5	1.521 (4)
S—O1	1.4610 (15)	C4—H4E	0.9900
S—N	1.6559 (18)	C4—H4A	0.9900
N—C1	1.481 (3)	C5—C6	1.534 (3)
N—H	0.83 (3)	C5—H5E	0.9900
C1—C6	1.525 (3)	C5—H5A	0.9900
C1—C2	1.526 (3)	C6—H6E	0.9900
C1—H1A	1.0000	C6—H6A	0.9900
C2—C3	1.530 (3)
H11—N1—H12	110 (3)	H2A—C2—H2E	108.0
H11—N1—H13	106 (3)	C4—C3—C2	111.4 (2)
H12—N1—H13	104 (3)	C4—C3—H3A	109.3
H11—N1—H14	118 (3)	C2—C3—H3A	109.3
H12—N1—H14	107 (3)	C4—C3—H3E	109.3
H13—N1—H14	111 (3)	C2—C3—H3E	109.3
O3—S—O2	112.12 (10)	H3A—C3—H3E	108.0
O3—S—O1	112.82 (10)	C5—C4—C3	110.9 (2)
O2—S—O1	112.30 (10)	C5—C4—H4E	109.5
O3—S—N	104.84 (10)	C3—C4—H4E	109.5
O2—S—N	111.14 (9)	C5—C4—H4A	109.5
O1—S—N	102.98 (9)	C3—C4—H4A	109.5
C1—N—S	117.99 (14)	H4E—C4—H4A	108.0
C1—N—H	112.5 (17)	C4—C5—C6	111.8 (2)
S—N—H	107.8 (17)	C4—C5—H5E	109.3
N—C1—C6	108.06 (17)	C6—C5—H5E	109.3
N—C1—C2	112.95 (18)	C4—C5—H5A	109.3
C6—C1—C2	110.90 (18)	C6—C5—H5A	109.3
N—C1—H1A	108.3	H5E—C5—H5A	107.9
C6—C1—H1A	108.3	C1—C6—C5	110.81 (19)
C2—C1—H1A	108.3	C1—C6—H6E	109.5
C1—C2—C3	111.04 (19)	C5—C6—H6E	109.5
C1—C2—H2A	109.4	C1—C6—H6A	109.5
C3—C2—H2A	109.4	C5—C6—H6A	109.5
C1—C2—H2E	109.4	H6E—C6—H6A	108.1
C3—C2—H2E	109.4
O3—S—N—C1	61.09 (18)	C3—C4—C5—C6	−55.1 (3)
O2—S—N—C1	−60.26 (18)	N—C1—C6—C5	179.99 (19)
O1—S—N—C1	179.30 (16)	C2—C1—C6—C5	−55.7 (3)
S—N—C1—C6	−154.92 (16)	C4—C5—C6—C1	55.5 (3)
S—N—C1—C2	82.0 (2)	C2—C1—N—S	82.0 (2)
N—C1—C2—C3	177.65 (19)	H1A—C1—N—H	−164.4
C6—C1—C2—C3	56.2 (3)	H—N—S—O1	−52.0 (18)
C1—C2—C3—C4	−56.0 (3)	H—N—S—O2	68.5 (18)
C2—C3—C4—C5	55.3 (3)	H—N—S—O3	−170.2 (18)

(V) Rubidium N-cyclohexylsulfamate

Crystal data

Rb^+·C6H12NSO3^−	F(000) = 1056
Mr = 263.70	Dx = 1.813 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2587 reflections
a = 34.039 (5) Å	θ = 1–29.1°
b = 6.451 (2) Å	µ = 5.31 mm^−1
c = 8.811 (2) Å	T = 293 K
β = 92.67 (1)°	Plate, colourless
V = 1932.7 (8) Å^3	0.12 × 0.11 × 0.09 mm
Z = 8

Data collection

Nonius KappaCCD diffractometer	2549 independent reflections
Radiation source: fine-focus sealed tube	2327 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
Detector resolution: 0.055 pixels mm^-1	θmax = 29.1°, θmin = 3.6°
ω scans	h = −45→46
Absorption correction: multi-scan DENZO and SCALEPACK (Otwinowski & Minor, 1997) based on the redundancy of symmetry-related measurements	k = −8→8
Tmin = 0.536, Tmax = 0.625	l = −12→12
10240 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.060	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0179P)^2 + 2.7361P] where P = (Fo^2 + 2Fc^2)/3
2549 reflections	(Δ/σ)max = 0.005
113 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.48 e Å^−3

Special details

Experimental. KappaCCD Nonius diffractometer. 198 frames in 3 sets of ω and ϕ scans. Rotation/frame=1.9°. Crystal-detector distance=35.00 mm. Measuring time=190 s/frame. Mosaicity=0.519 (2)°.

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
Rb	0.717743 (5)	0.56222 (3)	0.89219 (2)	0.02915 (7)
S	0.688699 (13)	0.07618 (7)	0.77764 (5)	0.02413 (10)
O1	0.72639 (4)	0.0498 (2)	0.86037 (17)	0.0360 (3)
O2	0.67141 (4)	−0.1206 (2)	0.73019 (17)	0.0349 (3)
O3	0.69081 (5)	0.2204 (2)	0.65171 (16)	0.0391 (3)
N	0.66161 (4)	0.1939 (3)	0.90040 (18)	0.0260 (3)
C1	0.61966 (5)	0.2295 (3)	0.8595 (2)	0.0287 (4)
H1A	0.6170	0.2559	0.7499	0.034*
C2	0.59374 (6)	0.0469 (3)	0.8958 (3)	0.0442 (5)
H2A	0.5975	0.0128	1.0027	0.053*
H2E	0.6015	−0.0726	0.8374	0.053*
C3	0.54993 (7)	0.0935 (4)	0.8591 (4)	0.0576 (7)
H3A	0.5456	0.1125	0.7504	0.069*
H3E	0.5342	−0.0234	0.8894	0.069*
C4	0.53709 (7)	0.2868 (5)	0.9410 (4)	0.0575 (7)
H4E	0.5101	0.3187	0.9099	0.069*
H4A	0.5382	0.2613	1.0496	0.069*
C5	0.56287 (8)	0.4693 (4)	0.9070 (4)	0.0619 (8)
H5E	0.5551	0.5872	0.9671	0.074*
H5A	0.5590	0.5060	0.8006	0.074*
C6	0.60674 (7)	0.4229 (4)	0.9421 (4)	0.0491 (6)
H6E	0.6224	0.5401	0.9115	0.059*
H6A	0.6113	0.4038	1.0507	0.059*
H	0.6649 (6)	0.139 (4)	0.981 (3)	0.027 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Rb	0.02909 (10)	0.02796 (10)	0.03049 (11)	−0.00103 (7)	0.00233 (7)	−0.00517 (7)
S	0.0236 (2)	0.0270 (2)	0.0220 (2)	0.00056 (16)	0.00342 (15)	0.00118 (16)
O1	0.0230 (6)	0.0496 (9)	0.0353 (8)	0.0031 (6)	0.0006 (5)	−0.0009 (6)
O2	0.0386 (8)	0.0310 (7)	0.0351 (8)	−0.0024 (6)	0.0007 (6)	−0.0059 (6)
O3	0.0478 (9)	0.0417 (8)	0.0287 (7)	0.0026 (7)	0.0119 (6)	0.0100 (6)
N	0.0248 (7)	0.0320 (8)	0.0213 (7)	0.0017 (6)	0.0037 (6)	0.0009 (6)
C1	0.0240 (8)	0.0316 (9)	0.0307 (9)	0.0033 (7)	0.0028 (7)	0.0022 (8)
C2	0.0285 (10)	0.0343 (11)	0.0701 (17)	−0.0015 (8)	0.0063 (10)	−0.0006 (11)
C3	0.0274 (11)	0.0535 (15)	0.092 (2)	−0.0019 (10)	0.0033 (12)	−0.0079 (14)
C4	0.0284 (11)	0.0649 (17)	0.0801 (19)	0.0048 (11)	0.0125 (11)	−0.0066 (15)
C5	0.0409 (13)	0.0456 (14)	0.100 (2)	0.0169 (11)	0.0165 (14)	−0.0011 (15)
C6	0.0359 (11)	0.0341 (11)	0.0784 (19)	0.0033 (9)	0.0137 (12)	−0.0111 (11)

Geometric parameters (Å, º)

Rb—N	3.0523 (17)	C2—H2A	0.9700
Rb—O3	3.1642 (17)	C2—H2E	0.9700
Rb—O1	3.3320 (19)	C3—C4	1.515 (4)
Rb—S	3.4255 (10)	C3—H3A	0.9700
S—O3	1.4523 (15)	C3—H3E	0.9700
S—O2	1.4526 (16)	C4—C5	1.507 (4)
S—O1	1.4558 (14)	C4—H4E	0.9700
S—N	1.6401 (16)	C4—H4A	0.9700
N—C1	1.474 (2)	C5—C6	1.540 (4)
N—H	0.80 (2)	C5—H5E	0.9700
C1—C2	1.515 (3)	C5—H5A	0.9700
C1—C6	1.520 (3)	C6—H6E	0.9700
C1—H1A	0.9800	C6—H6A	0.9700
C2—C3	1.541 (3)
N—Rb—O1	44.55 (4)	C3—C2—H2A	109.3
O3—Rb—O1	43.63 (4)	C1—C2—H2E	109.3
N—Rb—S	28.59 (3)	C3—C2—H2E	109.3
O3—Rb—S	25.06 (3)	H2A—C2—H2E	107.9
O1—Rb—S	24.83 (3)	C4—C3—C2	111.0 (2)
O3—S—O2	111.95 (9)	C4—C3—H3A	109.4
O3—S—O1	112.57 (9)	C2—C3—H3A	109.4
O2—S—O1	112.18 (9)	C4—C3—H3E	109.4
O3—S—N	104.87 (9)	C2—C3—H3E	109.4
O2—S—N	111.20 (9)	H3A—C3—H3E	108.0
O1—S—N	103.50 (9)	C5—C4—C3	111.4 (2)
O3—S—Rb	67.35 (7)	C5—C4—H4E	109.4
O2—S—Rb	172.88 (6)	C3—C4—H4E	109.4
O1—S—Rb	73.99 (7)	C5—C4—H4A	109.4
N—S—Rb	62.96 (6)	C3—C4—H4A	109.4
C1—N—S	118.61 (13)	H4E—C4—H4A	108.0
C1—N—Rb	118.22 (12)	C4—C5—C6	112.1 (2)
S—N—Rb	88.44 (6)	C4—C5—H5E	109.2
C1—N—H	112.5 (16)	C6—C5—H5E	109.2
S—N—H	108.8 (17)	C4—C5—H5A	109.2
Rb—N—H	107.6 (17)	C6—C5—H5A	109.2
N—C1—C2	113.19 (16)	H5E—C5—H5A	107.9
N—C1—C6	108.04 (17)	C1—C6—C5	111.3 (2)
C2—C1—C6	110.66 (18)	C1—C6—H6E	109.4
N—C1—H1A	108.3	C5—C6—H6E	109.4
C2—C1—H1A	108.3	C1—C6—H6A	109.4
C6—C1—H1A	108.3	C5—C6—H6A	109.4
C1—C2—C3	111.8 (2)	H6E—C6—H6A	108.0
C1—C2—H2A	109.3
O3—S—N—C1	67.25 (16)	C3—C4—C5—C6	−54.6 (4)
O2—S—N—C1	−53.93 (17)	N—C1—C6—C5	−179.2 (2)
O1—S—N—C1	−174.57 (14)	C2—C1—C6—C5	−54.7 (3)
S—N—C1—C2	85.8 (2)	C4—C5—C6—C1	54.7 (4)
S—N—C1—C6	−151.26 (16)	H1A—C1—N—H	−162.8
N—C1—C2—C3	177.1 (2)	C2—C1—N—S	85.8 (2)
C6—C1—C2—C3	55.7 (3)	H—N—S—O1	−44.2 (18)
C1—C2—C3—C4	−55.7 (3)	H—N—S—O2	76.4 (18)
C2—C3—C4—C5	54.6 (4)	H—N—S—O3	−162.4 (18)

(VI) Tetra-n-propylammonium N-cyclohexylsulfamate

Crystal data

C12H28N^+·C6H12NSO3^−	F(000) = 808
Mr = 364.58	Dx = 1.135 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5154 reflections
a = 10.9510 (11) Å	θ = 1–27.9°
b = 13.5112 (12) Å	µ = 0.17 mm^−1
c = 14.6202 (15) Å	T = 150 K
β = 99.425 (5)°	Prism, colourless
V = 2134.0 (4) Å^3	0.16 × 0.14 × 0.12 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	5074 independent reflections
Radiation source: fine-focus sealed tube	3955 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
Detector resolution: 0.055 pixels mm^-1	θmax = 27.9°, θmin = 2.5°
ω scans at κ = 55°	h = −14→14
Absorption correction: multi-scan DENZO and SCALEPACK (Otwinowski & Minor, 1997) based on the redundancy of symmetry-related measurements	k = −15→17
Tmin = 0.961, Tmax = 0.984	l = −19→19
25465 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0713P)^2 + 0.5733P] where P = (Fo^2 + 2Fc^2)/3
5074 reflections	(Δ/σ)max = 0.001
225 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.36 e Å^−3

Special details

Experimental. KappaCCD Nonius diffractometer. 177 frames in 5 sets of ω and ϕ scans at κ = 55°. Rotation/frame=2.0°. Crystal-detector distance=30.00 mm. Measuring time=220 s/frame. Mosaicity=0.501 (2)°.

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
S	0.50382 (3)	0.62736 (3)	0.61299 (3)	0.02077 (12)
O1	0.55103 (11)	0.62041 (8)	0.52572 (8)	0.0270 (3)
O2	0.43996 (11)	0.71962 (8)	0.62345 (9)	0.0303 (3)
O3	0.59806 (10)	0.60539 (8)	0.69363 (7)	0.0254 (3)
N	0.39667 (12)	0.53821 (11)	0.60445 (10)	0.0234 (3)
H	0.4158 (19)	0.4999 (17)	0.5742 (15)	0.034 (6)*
C1	0.37278 (14)	0.49240 (12)	0.69115 (11)	0.0234 (3)
H1A	0.4524 (16)	0.4706 (13)	0.7298 (12)	0.023 (4)*
C2	0.31411 (16)	0.56468 (13)	0.75102 (11)	0.0284 (4)
H2A	0.2353	0.5898	0.7157	0.034*
H2E	0.3701	0.6218	0.7672	0.034*
C3	0.28928 (17)	0.51419 (14)	0.83987 (12)	0.0335 (4)
H3A	0.3691	0.4955	0.8781	0.040*
H3E	0.2470	0.5613	0.8761	0.040*
C4	0.20942 (18)	0.42205 (15)	0.81894 (13)	0.0379 (4)
H4E	0.2018	0.3882	0.8778	0.046*
H4A	0.1254	0.4418	0.7886	0.046*
C5	0.26441 (19)	0.35100 (15)	0.75614 (14)	0.0411 (5)
H5E	0.2066	0.2952	0.7392	0.049*
H5A	0.3430	0.3238	0.7899	0.049*
C6	0.28899 (17)	0.40291 (13)	0.66783 (13)	0.0333 (4)
H6E	0.3285	0.3558	0.6298	0.040*
H6A	0.2094	0.4244	0.6310	0.040*
N1	0.78720 (12)	0.33559 (10)	0.65984 (9)	0.0237 (3)
C11	0.78421 (15)	0.43878 (12)	0.61733 (11)	0.0261 (3)
H11A	0.7718	0.4319	0.5490	0.031*
H11B	0.7117	0.4746	0.6333	0.031*
C12	0.89857 (16)	0.50116 (13)	0.64750 (12)	0.0322 (4)
H12A	0.9726	0.4656	0.6339	0.039*
H12B	0.9093	0.5128	0.7152	0.039*
C13	0.88631 (19)	0.59980 (15)	0.59660 (14)	0.0403 (5)
H13A	0.9606	0.6397	0.6166	0.060*
H13B	0.8135	0.6351	0.6107	0.060*
H13C	0.8770	0.5881	0.5297	0.060*
C21	0.81003 (15)	0.33991 (13)	0.76530 (11)	0.0260 (4)
H21A	0.8143	0.2713	0.7894	0.031*
H21B	0.8919	0.3708	0.7859	0.031*
C22	0.71415 (17)	0.39618 (14)	0.80905 (12)	0.0331 (4)
H22A	0.6342	0.3604	0.7978	0.040*
H22B	0.7014	0.4628	0.7809	0.040*
C23	0.7592 (2)	0.40560 (16)	0.91293 (13)	0.0417 (5)
H23A	0.6974	0.4415	0.9415	0.063*
H23B	0.8377	0.4419	0.9236	0.063*
H23C	0.7715	0.3395	0.9404	0.063*
C31	0.89081 (15)	0.27325 (13)	0.63303 (11)	0.0274 (4)
H31A	0.8892	0.2076	0.6629	0.033*
H31B	0.9707	0.3049	0.6585	0.033*
C32	0.88639 (18)	0.25788 (15)	0.52987 (13)	0.0369 (4)
H32A	0.8960	0.3222	0.4994	0.044*
H32B	0.8054	0.2293	0.5023	0.044*
C33	0.9901 (2)	0.18828 (16)	0.51432 (15)	0.0454 (5)
H33A	0.9874	0.1782	0.4476	0.068*
H33B	0.9797	0.1246	0.5441	0.068*
H33C	1.0700	0.2172	0.5411	0.068*
C41	0.66200 (15)	0.28975 (13)	0.62342 (12)	0.0283 (4)
H41A	0.5972	0.3303	0.6452	0.034*
H41B	0.6481	0.2934	0.5549	0.034*
C42	0.64541 (17)	0.18330 (14)	0.65138 (14)	0.0400 (5)
H42A	0.7050	0.1404	0.6260	0.048*
H42B	0.6614	0.1774	0.7198	0.048*
C43	0.5146 (2)	0.15077 (19)	0.61424 (19)	0.0594 (7)
H24A	0.5033	0.0819	0.6322	0.089*
H24B	0.4996	0.1562	0.5465	0.089*
H24C	0.4560	0.1932	0.6400	0.089*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.0222 (2)	0.0185 (2)	0.0207 (2)	0.00157 (14)	0.00070 (14)	−0.00094 (14)
O1	0.0324 (6)	0.0276 (6)	0.0215 (6)	−0.0016 (5)	0.0059 (5)	−0.0011 (5)
O2	0.0333 (6)	0.0195 (6)	0.0380 (7)	0.0063 (5)	0.0057 (5)	−0.0008 (5)
O3	0.0255 (6)	0.0247 (6)	0.0238 (6)	−0.0008 (4)	−0.0029 (5)	−0.0007 (4)
N	0.0256 (7)	0.0220 (7)	0.0221 (7)	−0.0013 (5)	0.0023 (5)	−0.0048 (6)
C1	0.0223 (7)	0.0210 (8)	0.0261 (8)	0.0003 (6)	0.0012 (6)	0.0004 (6)
C2	0.0328 (9)	0.0257 (8)	0.0271 (8)	0.0017 (7)	0.0062 (7)	−0.0016 (7)
C3	0.0352 (9)	0.0380 (10)	0.0278 (9)	−0.0020 (8)	0.0063 (7)	0.0011 (7)
C4	0.0360 (10)	0.0425 (11)	0.0357 (10)	−0.0087 (8)	0.0071 (8)	0.0069 (8)
C5	0.0450 (11)	0.0312 (10)	0.0471 (11)	−0.0120 (8)	0.0083 (9)	0.0037 (8)
C6	0.0358 (9)	0.0278 (9)	0.0364 (9)	−0.0075 (7)	0.0058 (7)	−0.0052 (7)
N1	0.0222 (6)	0.0248 (7)	0.0225 (7)	0.0036 (5)	−0.0008 (5)	0.0037 (5)
C11	0.0279 (8)	0.0254 (8)	0.0238 (8)	0.0054 (6)	0.0009 (6)	0.0061 (6)
C12	0.0341 (9)	0.0288 (9)	0.0323 (9)	−0.0003 (7)	0.0008 (7)	0.0026 (7)
C13	0.0460 (11)	0.0361 (11)	0.0388 (10)	−0.0064 (8)	0.0074 (9)	0.0087 (8)
C21	0.0269 (8)	0.0290 (9)	0.0206 (8)	0.0031 (7)	−0.0004 (6)	0.0057 (6)
C22	0.0347 (9)	0.0386 (10)	0.0259 (9)	0.0089 (8)	0.0046 (7)	0.0053 (7)
C23	0.0508 (12)	0.0481 (12)	0.0265 (9)	0.0021 (10)	0.0072 (8)	0.0015 (8)
C31	0.0270 (8)	0.0260 (8)	0.0282 (8)	0.0061 (6)	0.0014 (6)	0.0016 (7)
C32	0.0400 (10)	0.0404 (11)	0.0306 (9)	0.0077 (8)	0.0066 (8)	0.0019 (8)
C33	0.0577 (12)	0.0414 (11)	0.0393 (11)	0.0146 (10)	0.0144 (9)	−0.0025 (9)
C41	0.0240 (8)	0.0315 (9)	0.0265 (8)	−0.0003 (7)	−0.0047 (6)	0.0042 (7)
C42	0.0351 (9)	0.0355 (10)	0.0448 (11)	−0.0081 (8)	−0.0072 (8)	0.0103 (9)
C43	0.0409 (12)	0.0500 (14)	0.0790 (18)	−0.0153 (10)	−0.0144 (11)	0.0169 (12)

Geometric parameters (Å, º)

S—O2	1.4497 (12)	C12—H12B	0.9900
S—O1	1.4560 (12)	C13—H13A	0.9800
S—O3	1.4645 (11)	C13—H13B	0.9800
S—N	1.6720 (14)	C13—H13C	0.9800
N—C1	1.472 (2)	C21—C22	1.520 (2)
N—H	0.73 (2)	C21—H21A	0.9900
C1—C2	1.522 (2)	C21—H21B	0.9900
C1—C6	1.522 (2)	C22—C23	1.523 (2)
C1—H1A	1.003 (17)	C22—H22A	0.9900
C2—C3	1.530 (2)	C22—H22B	0.9900
C2—H2A	0.9900	C23—H23A	0.9800
C2—H2E	0.9900	C23—H23B	0.9800
C3—C4	1.523 (3)	C23—H23C	0.9800
C3—H3A	0.9900	C31—C32	1.515 (2)
C3—H3E	0.9900	C31—H31A	0.9900
C4—C5	1.519 (3)	C31—H31B	0.9900
C4—H4E	0.9900	C32—C33	1.520 (3)
C4—H4A	0.9900	C32—H32A	0.9900
C5—C6	1.531 (3)	C32—H32B	0.9900
C5—H5E	0.9900	C33—H33A	0.9800
C5—H5A	0.9900	C33—H33B	0.9800
C6—H6E	0.9900	C33—H33C	0.9800
C6—H6A	0.9900	C41—C42	1.514 (2)
N1—C31	1.515 (2)	C41—H41A	0.9900
N1—C41	1.519 (2)	C41—H41B	0.9900
N1—C21	1.522 (2)	C42—C43	1.512 (3)
N1—C11	1.525 (2)	C42—H42A	0.9900
C11—C12	1.514 (2)	C42—H42B	0.9900
C11—H11A	0.9900	C43—H24A	0.9800
C11—H11B	0.9900	C43—H24B	0.9800
C12—C13	1.522 (3)	C43—H24C	0.9800
C12—H12A	0.9900
O2—S—O1	113.25 (7)	H12A—C12—H12B	108.2
O2—S—O3	112.21 (7)	C12—C13—H13A	109.5
O1—S—O3	112.82 (7)	C12—C13—H13B	109.5
O2—S—N	106.41 (7)	H13A—C13—H13B	109.5
O1—S—N	103.51 (7)	C12—C13—H13C	109.5
O3—S—N	107.91 (7)	H13A—C13—H13C	109.5
C1—N—S	117.40 (10)	H13B—C13—H13C	109.5
C1—N—H	109.3 (17)	C22—C21—N1	115.81 (13)
S—N—H	106.7 (17)	C22—C21—H21A	108.3
N—C1—C2	112.12 (13)	N1—C21—H21A	108.3
N—C1—C6	109.06 (13)	C22—C21—H21B	108.3
C2—C1—C6	110.04 (14)	N1—C21—H21B	108.3
N—C1—H1A	110.4 (10)	H21A—C21—H21B	107.4
C2—C1—H1A	105.9 (10)	C21—C22—C23	109.15 (15)
C6—C1—H1A	109.2 (10)	C21—C22—H22A	109.9
C1—C2—C3	110.63 (14)	C23—C22—H22A	109.9
C1—C2—H2A	109.5	C21—C22—H22B	109.9
C3—C2—H2A	109.5	C23—C22—H22B	109.9
C1—C2—H2E	109.5	H22A—C22—H22B	108.3
C3—C2—H2E	109.5	C22—C23—H23A	109.5
H2A—C2—H2E	108.1	C22—C23—H23B	109.5
C4—C3—C2	111.70 (15)	H23A—C23—H23B	109.5
C4—C3—H3A	109.3	C22—C23—H23C	109.5
C2—C3—H3A	109.3	H23A—C23—H23C	109.5
C4—C3—H3E	109.3	H23B—C23—H23C	109.5
C2—C3—H3E	109.3	N1—C31—C32	115.49 (13)
H3A—C3—H3E	107.9	N1—C31—H31A	108.4
C5—C4—C3	111.50 (15)	C32—C31—H31A	108.4
C5—C4—H4E	109.3	N1—C31—H31B	108.4
C3—C4—H4E	109.3	C32—C31—H31B	108.4
C5—C4—H4A	109.3	H31A—C31—H31B	107.5
C3—C4—H4A	109.3	C31—C32—C33	109.32 (15)
H4E—C4—H4A	108.0	C31—C32—H32A	109.8
C4—C5—C6	111.21 (17)	C33—C32—H32A	109.8
C4—C5—H5E	109.4	C31—C32—H32B	109.8
C6—C5—H5E	109.4	C33—C32—H32B	109.8
C4—C5—H5A	109.4	H32A—C32—H32B	108.3
C6—C5—H5A	109.4	C32—C33—H33A	109.5
H5E—C5—H5A	108.0	C32—C33—H33B	109.5
C1—C6—C5	110.95 (15)	H33A—C33—H33B	109.5
C1—C6—H6E	109.4	C32—C33—H33C	109.5
C5—C6—H6E	109.4	H33A—C33—H33C	109.5
C1—C6—H6A	109.4	H33B—C33—H33C	109.5
C5—C6—H6A	109.4	C42—C41—N1	115.72 (13)
H6E—C6—H6A	108.0	C42—C41—H41A	108.4
C31—N1—C41	110.72 (13)	N1—C41—H41A	108.4
C31—N1—C21	106.12 (11)	C42—C41—H41B	108.4
C41—N1—C21	111.08 (12)	N1—C41—H41B	108.4
C31—N1—C11	111.71 (12)	H41A—C41—H41B	107.4
C41—N1—C11	105.79 (12)	C43—C42—C41	109.13 (16)
C21—N1—C11	111.52 (12)	C43—C42—H42A	109.9
C12—C11—N1	115.39 (13)	C41—C42—H42A	109.9
C12—C11—H11A	108.4	C43—C42—H42B	109.9
N1—C11—H11A	108.4	C41—C42—H42B	109.9
C12—C11—H11B	108.4	H42A—C42—H42B	108.3
N1—C11—H11B	108.4	C42—C43—H24A	109.5
H11A—C11—H11B	107.5	C42—C43—H24B	109.5
C11—C12—C13	110.03 (14)	H24A—C43—H24B	109.5
C11—C12—H12A	109.7	C42—C43—H24C	109.5
C13—C12—H12A	109.7	H24A—C43—H24C	109.5
C11—C12—H12B	109.7	H24B—C43—H24C	109.5
C13—C12—H12B	109.7
O2—S—N—C1	−88.91 (13)	C31—N1—C21—C22	−177.91 (15)
O1—S—N—C1	151.49 (12)	C41—N1—C21—C22	−57.51 (19)
O3—S—N—C1	31.70 (14)	C11—N1—C21—C22	60.23 (18)
S—N—C1—C2	67.01 (16)	N1—C21—C22—C23	−172.35 (15)
S—N—C1—C6	−170.86 (12)	C41—N1—C31—C32	58.84 (19)
N—C1—C2—C3	179.34 (13)	C21—N1—C31—C32	179.48 (15)
C6—C1—C2—C3	57.76 (18)	C11—N1—C31—C32	−58.79 (18)
C1—C2—C3—C4	−55.89 (19)	N1—C31—C32—C33	−175.92 (16)
C2—C3—C4—C5	53.9 (2)	C31—N1—C41—C42	54.98 (19)
C3—C4—C5—C6	−53.8 (2)	C21—N1—C41—C42	−62.67 (19)
N—C1—C6—C5	178.43 (15)	C11—N1—C41—C42	176.17 (15)
C2—C1—C6—C5	−58.19 (19)	N1—C41—C42—C43	176.91 (17)
C4—C5—C6—C1	56.3 (2)	H1A—C1—N—H	71 (2)
C31—N1—C11—C12	−62.12 (18)	C2—C1—N—S	67.01 (16)
C41—N1—C11—C12	177.33 (14)	H—N—S—O1	28.5 (17)
C21—N1—C11—C12	56.45 (18)	H—N—S—O2	148.1 (17)
N1—C11—C12—C13	177.17 (15)	H—N—S—O3	−91.3 (17)