Cyclo-hex-yl(meth-yl)ammonium {bis-[cyclo-hex-yl(meth-yl)amino]-phosphor-yl}(4-methyl-phenyl-sulfon-yl)aza-nide.

In the anion of the title salt, C(7)H(16)N(+)·C(21)H(35)N(3)O(3)PS(-), the P and S atoms are both in distorted tetra-hedral environments and the angles at the tertiary N atoms confirm their sp(2) character. The two S=O groups are in syn and gauche conformations with respect to the phosphoryl group. In the crystal, N-H⋯O(=S) and N-H⋯O(=P) hydrogen bonds involving two anions and two cations form a centrosymmetric four-component cluster.

Related literature

For related structures see: Yazdanbakhsh et al. (2009 ▶); Pourayoubi et al. (2011 ▶).

Experimental

Crystal data

pan class="Chemical">C7H16N+·pan class="Chemical">C21H35N3O3PS−

M = 554.76

Triclinic,

a = 10.6514 (5) Å

b = 11.5984 (5) Å

c = 13.5681 (6) Å

α = 103.738 (3)°

β = 97.201 (2)°

γ = 107.584 (2)°

V = 1516.59 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.19 mm−1

T = 173 K

0.11 × 0.10 × 0.01 mm

Data collection

Nonius KappaCCD diffractometer with Apan class="Chemical">PEXII CCD

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.979, T max = 0.998

24576 measured reflections

7401 independent reflections

4499 reflections with I > 2σ(I)

R int = 0.160

Refinement

R[F 2 > 2σ(F 2)] = 0.085

wR(F 2) = 0.189

S = 1.07

7401 reflections

338 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.48 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEpan class="Chemical">PACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular grapn>hics: Mercury (Macrae et al., 2008 ▶); software used to prepn>are material for publication: enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681103950X/lh5320sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103950X/lh5320Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681103950X/lh5320Isup3.cml

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

C7H16N+·C21H35N3O3PS−	Z = 2
Mr = 554.76	F(000) = 604
Triclinic, P1	Dx = 1.215 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.6514 (5) Å	Cell parameters from 4260 reflections
b = 11.5984 (5) Å	θ = 1.6–28.3°
c = 13.5681 (6) Å	µ = 0.19 mm−1
α = 103.738 (3)°	T = 173 K
β = 97.201 (2)°	Prism, colorless
γ = 107.584 (2)°	0.11 × 0.10 × 0.01 mm
V = 1516.59 (12) Å3

Nonius KappaCCD diffractometer with APEXII CCD	7401 independent reflections
Radiation source: fine-focus sealed tube	4499 reflections with I > 2σ(I)
graphite	Rint = 0.160
ω and φ scans	θmax = 28.3°, θmin = 1.6°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −14→14
Tmin = 0.979, Tmax = 0.998	k = −15→15
24576 measured reflections	l = −17→18

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.085	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.189	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.P)2 + 3.380P] where P = (Fo2 + 2Fc2)/3
7401 reflections	(Δ/σ)max = 0.003
338 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.48 e Å−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.

	x	y	z	Uiso*/Ueq
S1	0.70329 (9)	0.92657 (8)	0.36570 (7)	0.0249 (2)
P1	0.79120 (10)	0.92027 (9)	0.17273 (7)	0.0240 (2)
O1	0.9263 (3)	0.9142 (2)	0.20889 (19)	0.0309 (6)
O2	0.8350 (2)	0.9315 (2)	0.41750 (19)	0.0292 (6)
O3	0.6634 (3)	1.0300 (2)	0.4178 (2)	0.0337 (6)
N1	0.6862 (3)	0.9065 (3)	0.2483 (2)	0.0254 (7)
N2	0.7991 (3)	1.0530 (3)	0.1422 (2)	0.0271 (7)
N3	0.7199 (3)	0.8094 (3)	0.0606 (2)	0.0291 (7)
C1	0.5849 (4)	0.7865 (3)	0.3761 (3)	0.0261 (8)
C2	0.5958 (4)	0.6703 (4)	0.3313 (3)	0.0355 (10)
H2	0.6642	0.6656	0.2934	0.043*
C3	0.5076 (5)	0.5618 (4)	0.3417 (3)	0.0412 (10)
H3	0.5165	0.4828	0.3111	0.049*
C4	0.4056 (4)	0.5647 (4)	0.3959 (3)	0.0374 (10)
C5	0.3963 (4)	0.6819 (4)	0.4392 (3)	0.0415 (11)
H5	0.3271	0.6866	0.4762	0.050*
C6	0.4843 (4)	0.7921 (4)	0.4303 (3)	0.0334 (9)
H6	0.4759	0.8713	0.4612	0.040*
C7	0.3111 (5)	0.4448 (5)	0.4076 (4)	0.0595 (14)
H7A	0.2376	0.4627	0.4376	0.071*
H7B	0.3604	0.4119	0.4534	0.071*
H7C	0.2738	0.3819	0.3393	0.071*
C8	0.8916 (4)	1.0830 (4)	0.0727 (3)	0.0364 (10)
H8A	0.8660	1.1381	0.0356	0.044*
H8B	0.8867	1.0046	0.0225	0.044*
H8C	0.9840	1.1263	0.1137	0.044*
C9	0.7912 (4)	1.1622 (3)	0.2199 (3)	0.0263 (8)
H9	0.7191	1.1282	0.2566	0.032*
C10	0.7481 (4)	1.2506 (4)	0.1686 (3)	0.0350 (9)
H10A	0.6627	1.2024	0.1168	0.042*
H10B	0.8175	1.2868	0.1316	0.042*
C11	0.7284 (5)	1.3574 (4)	0.2483 (4)	0.0432 (11)
H11A	0.6547	1.3218	0.2820	0.052*
H11B	0.7025	1.4149	0.2130	0.052*
C12	0.8583 (5)	1.4315 (4)	0.3306 (4)	0.0530 (13)
H12A	0.9299	1.4733	0.2977	0.064*
H12B	0.8430	1.4979	0.3836	0.064*
C13	0.9034 (5)	1.3434 (4)	0.3824 (4)	0.0473 (12)
H13A	0.8356	1.3084	0.4210	0.057*
H13B	0.9899	1.3921	0.4329	0.057*
C14	0.9211 (4)	1.2349 (4)	0.3028 (3)	0.0340 (9)
H14A	0.9450	1.1768	0.3384	0.041*
H14B	0.9958	1.2691	0.2694	0.041*
C15	0.5777 (4)	0.7821 (4)	0.0194 (3)	0.0363 (9)
H15A	0.5591	0.7524	−0.0566	0.044*
H15B	0.5555	0.8590	0.0415	0.044*
H15C	0.5228	0.7164	0.0457	0.044*
C16	0.7784 (4)	0.7114 (3)	0.0248 (3)	0.0295 (8)
H16	0.8779	0.7504	0.0531	0.035*
C17	0.7285 (7)	0.5975 (5)	0.0641 (5)	0.075 (2)
H17A	0.6301	0.5556	0.0371	0.089*
H17B	0.7453	0.6253	0.1409	0.089*
C18	0.7997 (9)	0.5038 (6)	0.0296 (5)	0.096 (3)
H18A	0.8963	0.5427	0.0640	0.115*
H18B	0.7609	0.4279	0.0521	0.115*
C19	0.7873 (6)	0.4648 (4)	−0.0850 (5)	0.0689 (17)
H19A	0.6922	0.4137	−0.1192	0.083*
H19B	0.8429	0.4113	−0.1027	0.083*
C20	0.8317 (5)	0.5767 (4)	−0.1252 (4)	0.0472 (12)
H20A	0.8147	0.5476	−0.2019	0.057*
H20B	0.9299	0.6211	−0.0987	0.057*
C21	0.7576 (5)	0.6686 (4)	−0.0922 (3)	0.0388 (10)
H21A	0.7916	0.7429	−0.1178	0.047*
H21B	0.6601	0.6267	−0.1233	0.047*
N4	0.9037 (3)	1.0830 (3)	0.6297 (2)	0.0253 (7)
H41	0.9713	1.0780	0.6760	0.030*
H42	0.8916	1.0232	0.5677	0.030*
C22	0.7756 (4)	1.0497 (3)	0.6696 (3)	0.0274 (8)
H22	0.7016	1.0541	0.6190	0.033*
C23	0.7914 (4)	1.1430 (4)	0.7748 (3)	0.0331 (9)
H23A	0.8685	1.1440	0.8245	0.040*
H23B	0.8105	1.2291	0.7674	0.040*
C24	0.6636 (4)	1.1058 (4)	0.8168 (3)	0.0411 (10)
H24A	0.6785	1.1633	0.8873	0.049*
H24B	0.5894	1.1158	0.7717	0.049*
C25	0.6227 (5)	0.9703 (4)	0.8216 (3)	0.0453 (11)
H25A	0.5353	0.9476	0.8433	0.054*
H25B	0.6909	0.9628	0.8740	0.054*
C26	0.6099 (4)	0.8787 (4)	0.7162 (3)	0.0426 (11)
H26A	0.5894	0.7921	0.7226	0.051*
H26B	0.5344	0.8788	0.6656	0.051*
C27	0.7398 (4)	0.9157 (4)	0.6762 (3)	0.0346 (9)
H27A	0.8140	0.9089	0.7236	0.042*
H27B	0.7278	0.8572	0.6067	0.042*
C28	0.9490 (4)	1.2093 (4)	0.6132 (3)	0.0357 (9)
H28A	0.8743	1.2203	0.5710	0.043*
H28B	1.0240	1.2167	0.5771	0.043*
H28C	0.9790	1.2745	0.6805	0.043*

	U11	U22	U33	U12	U13	U23
S1	0.0237 (5)	0.0258 (5)	0.0231 (5)	0.0096 (4)	0.0021 (4)	0.0033 (4)
P1	0.0224 (5)	0.0250 (5)	0.0216 (5)	0.0097 (4)	−0.0008 (4)	0.0024 (4)
O1	0.0244 (14)	0.0409 (15)	0.0249 (14)	0.0162 (12)	−0.0014 (11)	0.0021 (12)
O2	0.0231 (14)	0.0383 (15)	0.0215 (13)	0.0109 (12)	−0.0012 (11)	0.0030 (11)
O3	0.0385 (17)	0.0281 (14)	0.0351 (15)	0.0163 (12)	0.0072 (13)	0.0040 (12)
N1	0.0211 (16)	0.0304 (16)	0.0250 (16)	0.0092 (13)	0.0027 (13)	0.0094 (13)
N2	0.0262 (17)	0.0276 (16)	0.0267 (16)	0.0089 (13)	0.0067 (14)	0.0065 (13)
N3	0.0247 (17)	0.0291 (17)	0.0270 (17)	0.0129 (14)	−0.0058 (14)	−0.0023 (14)
C1	0.0237 (19)	0.034 (2)	0.0203 (18)	0.0117 (16)	−0.0006 (15)	0.0075 (16)
C2	0.041 (3)	0.029 (2)	0.037 (2)	0.0111 (18)	0.018 (2)	0.0093 (18)
C3	0.052 (3)	0.030 (2)	0.040 (2)	0.013 (2)	0.012 (2)	0.0072 (19)
C4	0.030 (2)	0.042 (2)	0.035 (2)	0.0017 (18)	0.0061 (19)	0.015 (2)
C5	0.027 (2)	0.059 (3)	0.044 (3)	0.014 (2)	0.017 (2)	0.021 (2)
C6	0.026 (2)	0.039 (2)	0.036 (2)	0.0147 (18)	0.0085 (18)	0.0075 (18)
C7	0.049 (3)	0.056 (3)	0.061 (3)	−0.005 (2)	0.011 (3)	0.024 (3)
C8	0.042 (3)	0.036 (2)	0.031 (2)	0.0106 (19)	0.0165 (19)	0.0087 (18)
C9	0.031 (2)	0.0207 (18)	0.0281 (19)	0.0106 (15)	0.0094 (17)	0.0048 (15)
C10	0.035 (2)	0.034 (2)	0.038 (2)	0.0140 (18)	0.0060 (19)	0.0136 (19)
C11	0.055 (3)	0.038 (2)	0.052 (3)	0.027 (2)	0.025 (2)	0.019 (2)
C12	0.068 (4)	0.029 (2)	0.060 (3)	0.016 (2)	0.028 (3)	0.003 (2)
C13	0.052 (3)	0.039 (3)	0.038 (2)	0.013 (2)	0.006 (2)	−0.005 (2)
C14	0.036 (2)	0.029 (2)	0.028 (2)	0.0079 (17)	0.0038 (18)	−0.0011 (17)
C15	0.030 (2)	0.036 (2)	0.035 (2)	0.0099 (18)	0.0003 (18)	0.0016 (18)
C16	0.030 (2)	0.030 (2)	0.027 (2)	0.0127 (17)	0.0027 (17)	0.0039 (16)
C17	0.139 (6)	0.066 (4)	0.074 (4)	0.069 (4)	0.077 (4)	0.049 (3)
C18	0.194 (8)	0.079 (4)	0.089 (5)	0.103 (5)	0.088 (5)	0.060 (4)
C19	0.089 (4)	0.035 (3)	0.089 (4)	0.027 (3)	0.050 (4)	0.006 (3)
C20	0.060 (3)	0.044 (3)	0.036 (2)	0.019 (2)	0.020 (2)	0.003 (2)
C21	0.044 (3)	0.039 (2)	0.032 (2)	0.015 (2)	0.010 (2)	0.0062 (19)
N4	0.0235 (16)	0.0256 (16)	0.0245 (16)	0.0090 (13)	0.0020 (13)	0.0036 (13)
C22	0.0214 (19)	0.031 (2)	0.0277 (19)	0.0089 (16)	0.0008 (16)	0.0072 (16)
C23	0.032 (2)	0.031 (2)	0.038 (2)	0.0147 (17)	0.0093 (18)	0.0076 (18)
C24	0.036 (2)	0.056 (3)	0.034 (2)	0.023 (2)	0.010 (2)	0.008 (2)
C25	0.033 (2)	0.065 (3)	0.039 (3)	0.011 (2)	0.013 (2)	0.022 (2)
C26	0.031 (2)	0.047 (3)	0.044 (3)	0.0015 (19)	0.005 (2)	0.018 (2)
C27	0.033 (2)	0.032 (2)	0.033 (2)	0.0078 (17)	0.0027 (18)	0.0044 (18)
C28	0.039 (2)	0.031 (2)	0.041 (2)	0.0134 (18)	0.007 (2)	0.0161 (19)

S1—O3	1.449 (3)	C14—H14B	0.9900
S1—O2	1.466 (3)	C15—H15A	0.9800
S1—N1	1.533 (3)	C15—H15B	0.9800
S1—C1	1.779 (4)	C15—H15C	0.9800
P1—O1	1.489 (3)	C16—C21	1.512 (5)
P1—N1	1.608 (3)	C16—C17	1.515 (6)
P1—N3	1.654 (3)	C16—H16	1.0000
P1—N2	1.668 (3)	C17—C18	1.523 (7)
N2—C8	1.471 (5)	C17—H17A	0.9900
N2—C9	1.475 (4)	C17—H17B	0.9900
N3—C15	1.456 (5)	C18—C19	1.489 (8)
N3—C16	1.469 (5)	C18—H18A	0.9900
C1—C6	1.382 (5)	C18—H18B	0.9900
C1—C2	1.386 (5)	C19—C20	1.495 (6)
C2—C3	1.375 (5)	C19—H19A	0.9900
C2—H2	0.9500	C19—H19B	0.9900
C3—C4	1.391 (6)	C20—C21	1.526 (6)
C3—H3	0.9500	C20—H20A	0.9900
C4—C5	1.385 (6)	C20—H20B	0.9900
C4—C7	1.506 (6)	C21—H21A	0.9900
C5—C6	1.381 (6)	C21—H21B	0.9900
C5—H5	0.9500	N4—C28	1.478 (4)
C6—H6	0.9500	N4—C22	1.506 (5)
C7—H7A	0.9800	N4—H41	0.9200
C7—H7B	0.9800	N4—H42	0.9200
C7—H7C	0.9800	C22—C27	1.511 (5)
C8—H8A	0.9800	C22—C23	1.528 (5)
C8—H8B	0.9800	C22—H22	1.0000
C8—H8C	0.9800	C23—C24	1.523 (6)
C9—C10	1.512 (5)	C23—H23A	0.9900
C9—C14	1.532 (5)	C23—H23B	0.9900
C9—H9	1.0000	C24—C25	1.519 (6)
C10—C11	1.525 (5)	C24—H24A	0.9900
C10—H10A	0.9900	C24—H24B	0.9900
C10—H10B	0.9900	C25—C26	1.528 (6)
C11—C12	1.529 (7)	C25—H25A	0.9900
C11—H11A	0.9900	C25—H25B	0.9900
C11—H11B	0.9900	C26—C27	1.527 (6)
C12—C13	1.524 (7)	C26—H26A	0.9900
C12—H12A	0.9900	C26—H26B	0.9900
C12—H12B	0.9900	C27—H27A	0.9900
C13—C14	1.527 (5)	C27—H27B	0.9900
C13—H13A	0.9900	C28—H28A	0.9800
C13—H13B	0.9900	C28—H28B	0.9800
C14—H14A	0.9900	C28—H28C	0.9800
O3—S1—O2	112.95 (16)	N3—C15—H15C	109.5
O3—S1—N1	112.97 (16)	H15A—C15—H15C	109.5
O2—S1—N1	114.45 (16)	H15B—C15—H15C	109.5
O3—S1—C1	106.07 (17)	N3—C16—C21	112.2 (3)
O2—S1—C1	105.50 (16)	N3—C16—C17	113.7 (3)
N1—S1—C1	103.78 (17)	C21—C16—C17	109.6 (4)
O1—P1—N1	118.19 (15)	N3—C16—H16	107.0
O1—P1—N3	107.98 (15)	C21—C16—H16	107.0
N1—P1—N3	108.32 (16)	C17—C16—H16	107.0
O1—P1—N2	113.12 (16)	C16—C17—C18	110.8 (4)
N1—P1—N2	105.11 (15)	C16—C17—H17A	109.5
N3—P1—N2	103.00 (16)	C18—C17—H17A	109.5
S1—N1—P1	133.1 (2)	C16—C17—H17B	109.5
C8—N2—C9	115.9 (3)	C18—C17—H17B	109.5
C8—N2—P1	113.6 (2)	H17A—C17—H17B	108.1
C9—N2—P1	120.2 (2)	C19—C18—C17	112.5 (5)
C15—N3—C16	118.1 (3)	C19—C18—H18A	109.1
C15—N3—P1	117.7 (3)	C17—C18—H18A	109.1
C16—N3—P1	120.2 (2)	C19—C18—H18B	109.1
C6—C1—C2	119.6 (4)	C17—C18—H18B	109.1
C6—C1—S1	120.9 (3)	H18A—C18—H18B	107.8
C2—C1—S1	119.5 (3)	C18—C19—C20	111.6 (4)
C3—C2—C1	120.0 (4)	C18—C19—H19A	109.3
C3—C2—H2	120.0	C20—C19—H19A	109.3
C1—C2—H2	120.0	C18—C19—H19B	109.3
C2—C3—C4	121.7 (4)	C20—C19—H19B	109.3
C2—C3—H3	119.2	H19A—C19—H19B	108.0
C4—C3—H3	119.2	C19—C20—C21	111.6 (4)
C5—C4—C3	117.2 (4)	C19—C20—H20A	109.3
C5—C4—C7	122.0 (4)	C21—C20—H20A	109.3
C3—C4—C7	120.8 (4)	C19—C20—H20B	109.3
C6—C5—C4	122.1 (4)	C21—C20—H20B	109.3
C6—C5—H5	118.9	H20A—C20—H20B	108.0
C4—C5—H5	118.9	C16—C21—C20	110.4 (4)
C5—C6—C1	119.5 (4)	C16—C21—H21A	109.6
C5—C6—H6	120.3	C20—C21—H21A	109.6
C1—C6—H6	120.3	C16—C21—H21B	109.6
C4—C7—H7A	109.5	C20—C21—H21B	109.6
C4—C7—H7B	109.5	H21A—C21—H21B	108.1
H7A—C7—H7B	109.5	C28—N4—C22	115.7 (3)
C4—C7—H7C	109.5	C28—N4—H41	108.3
H7A—C7—H7C	109.5	C22—N4—H41	108.3
H7B—C7—H7C	109.5	C28—N4—H42	108.3
N2—C8—H8A	109.5	C22—N4—H42	108.3
N2—C8—H8B	109.5	H41—N4—H42	107.4
H8A—C8—H8B	109.5	N4—C22—C27	108.8 (3)
N2—C8—H8C	109.5	N4—C22—C23	110.7 (3)
H8A—C8—H8C	109.5	C27—C22—C23	111.4 (3)
H8B—C8—H8C	109.5	N4—C22—H22	108.6
N2—C9—C10	111.3 (3)	C27—C22—H22	108.6
N2—C9—C14	113.7 (3)	C23—C22—H22	108.6
C10—C9—C14	110.6 (3)	C24—C23—C22	110.5 (3)
N2—C9—H9	106.9	C24—C23—H23A	109.5
C10—C9—H9	106.9	C22—C23—H23A	109.5
C14—C9—H9	106.9	C24—C23—H23B	109.5
C9—C10—C11	111.2 (3)	C22—C23—H23B	109.5
C9—C10—H10A	109.4	H23A—C23—H23B	108.1
C11—C10—H10A	109.4	C25—C24—C23	112.0 (3)
C9—C10—H10B	109.4	C25—C24—H24A	109.2
C11—C10—H10B	109.4	C23—C24—H24A	109.2
H10A—C10—H10B	108.0	C25—C24—H24B	109.2
C10—C11—C12	110.4 (4)	C23—C24—H24B	109.2
C10—C11—H11A	109.6	H24A—C24—H24B	107.9
C12—C11—H11A	109.6	C24—C25—C26	111.1 (3)
C10—C11—H11B	109.6	C24—C25—H25A	109.4
C12—C11—H11B	109.6	C26—C25—H25A	109.4
H11A—C11—H11B	108.1	C24—C25—H25B	109.4
C13—C12—C11	110.4 (4)	C26—C25—H25B	109.4
C13—C12—H12A	109.6	H25A—C25—H25B	108.0
C11—C12—H12A	109.6	C27—C26—C25	111.1 (3)
C13—C12—H12B	109.6	C27—C26—H26A	109.4
C11—C12—H12B	109.6	C25—C26—H26A	109.4
H12A—C12—H12B	108.1	C27—C26—H26B	109.4
C12—C13—C14	111.5 (4)	C25—C26—H26B	109.4
C12—C13—H13A	109.3	H26A—C26—H26B	108.0
C14—C13—H13A	109.3	C22—C27—C26	110.2 (3)
C12—C13—H13B	109.3	C22—C27—H27A	109.6
C14—C13—H13B	109.3	C26—C27—H27A	109.6
H13A—C13—H13B	108.0	C22—C27—H27B	109.6
C13—C14—C9	110.6 (3)	C26—C27—H27B	109.6
C13—C14—H14A	109.5	H27A—C27—H27B	108.1
C9—C14—H14A	109.5	N4—C28—H28A	109.5
C13—C14—H14B	109.5	N4—C28—H28B	109.5
C9—C14—H14B	109.5	H28A—C28—H28B	109.5
H14A—C14—H14B	108.1	N4—C28—H28C	109.5
N3—C15—H15A	109.5	H28A—C28—H28C	109.5
N3—C15—H15B	109.5	H28B—C28—H28C	109.5
H15A—C15—H15B	109.5
O3—S1—N1—P1	114.9 (3)	C8—N2—C9—C10	58.5 (4)
O2—S1—N1—P1	−16.2 (3)	P1—N2—C9—C10	−158.7 (3)
C1—S1—N1—P1	−130.6 (3)	C8—N2—C9—C14	−67.3 (4)
O1—P1—N1—S1	21.6 (3)	P1—N2—C9—C14	75.6 (4)
N3—P1—N1—S1	144.7 (3)	N2—C9—C10—C11	175.2 (3)
N2—P1—N1—S1	−105.7 (3)	C14—C9—C10—C11	−57.4 (4)
O1—P1—N2—C8	49.5 (3)	C9—C10—C11—C12	57.8 (5)
N1—P1—N2—C8	179.8 (3)	C10—C11—C12—C13	−56.6 (5)
N3—P1—N2—C8	−66.8 (3)	C11—C12—C13—C14	56.2 (5)
O1—P1—N2—C9	−94.2 (3)	C12—C13—C14—C9	−55.7 (5)
N1—P1—N2—C9	36.2 (3)	N2—C9—C14—C13	−178.0 (3)
N3—P1—N2—C9	149.5 (3)	C10—C9—C14—C13	55.9 (4)
O1—P1—N3—C15	169.1 (3)	C15—N3—C16—C21	55.4 (5)
N1—P1—N3—C15	40.0 (3)	P1—N3—C16—C21	−147.6 (3)
N2—P1—N3—C15	−71.0 (3)	C15—N3—C16—C17	−69.7 (5)
O1—P1—N3—C16	12.0 (3)	P1—N3—C16—C17	87.4 (4)
N1—P1—N3—C16	−117.1 (3)	N3—C16—C17—C18	−176.5 (5)
N2—P1—N3—C16	131.9 (3)	C21—C16—C17—C18	57.0 (6)
O3—S1—C1—C6	−2.8 (4)	C16—C17—C18—C19	−55.0 (8)
O2—S1—C1—C6	117.3 (3)	C17—C18—C19—C20	53.1 (8)
N1—S1—C1—C6	−122.0 (3)	C18—C19—C20—C21	−54.1 (7)
O3—S1—C1—C2	178.9 (3)	N3—C16—C21—C20	174.4 (3)
O2—S1—C1—C2	−61.1 (3)	C17—C16—C21—C20	−58.3 (5)
N1—S1—C1—C2	59.6 (3)	C19—C20—C21—C16	57.2 (5)
C6—C1—C2—C3	−0.5 (6)	C28—N4—C22—C27	176.8 (3)
S1—C1—C2—C3	177.9 (3)	C28—N4—C22—C23	−60.4 (4)
C1—C2—C3—C4	0.4 (7)	N4—C22—C23—C24	−177.7 (3)
C2—C3—C4—C5	0.1 (7)	C27—C22—C23—C24	−56.5 (4)
C2—C3—C4—C7	−179.2 (4)	C22—C23—C24—C25	54.5 (5)
C3—C4—C5—C6	−0.5 (7)	C23—C24—C25—C26	−54.2 (5)
C7—C4—C5—C6	178.8 (4)	C24—C25—C26—C27	55.2 (5)
C4—C5—C6—C1	0.4 (6)	N4—C22—C27—C26	−179.8 (3)
C2—C1—C6—C5	0.1 (6)	C23—C22—C27—C26	57.8 (4)
S1—C1—C6—C5	−178.3 (3)	C25—C26—C27—C22	−57.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H42···O2	0.92	1.98	2.864 (4)	160.
N4—H41···O1i	0.92	1.76	2.648 (4)	163.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H42⋯O2	0.92	1.98	2.864 (4)	160
N4—H41⋯O1i	0.92	1.76	2.648 (4)	163

Symmetry code: (i) .