Bis(2-amino-5-benzyl-3-eth-oxy-carbonyl-4,5,6,7-tetra-hydro-thieno[3,2-c]pyridin-5-ium) bis-(4-meth-oxy-phen-yl)di-phos-phon-ate.

The asymmetric unit of the title salt, 2C17H21N2O2S(+)·C14H14O7P2 (2-), contains half of a centrosymmetric bis-(4-meth-oxy-phen-yl)di-phospho-nate anion and one 2-amino-5-benzyl-3-eth-oxy-carbonyl-4,5,6,7-tetra-hydro-thieno[3,2-c]pyri-din-5-ium cation. In the anion, the O atoms of the di-phospho-nate group are disordered over two positions with equal occupancies. In the cation, the ethyl group is disordered over two orientations with a refined occupancy ratio of 0.753 (5):0.247 (5), and the tetra-hydro-pyridinium ring adopts a distorted half-chair conformation. In the crystal, the ions are linked by C-H⋯O, N-H⋯O and C-H⋯S hydrogen bonds into a three-dimensional network.

Related literature

For medicinal applications of tetra­hydro­thieno­pyridines, see: Bernardino et al. (2006 ▶); Attaby et al. (1999 ▶); Kling et al. (2005 ▶); Baker & White (2009 ▶); Huber et al. (2009 ▶); Andersen et al. (2002 ▶); Boschellia et al. (2005 ▶); Tumeya et al. (2008 ▶). For a similar structure, see: Meng et al. (2011 ▶). For analysis of ring puckering, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

2C17H21N2O2S+·C14H14O7P2 2−

M = 991.05

Monoclinic,

a = 14.9420 (9) Å

b = 10.8718 (7) Å

c = 16.0773 (10) Å

β = 114.3270 (8)°

V = 2379.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.24 mm−1

T = 150 K

0.23 × 0.19 × 0.05 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.81, T max = 0.99

41576 measured reflections

5955 independent reflections

4481 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.132

S = 1.04

5955 reflections

317 parameters

28 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.77 e Å−3

Δρmin = −0.62 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814003766/rz5105sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814003766/rz5105Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814003766/rz5105Isup3.cml

CCDC reference: 987723

Additional supporting information: crystallographic information; 3D view; checkCIF report

2C17H21N2O2S+·C14H14O7P22−	F(000) = 1044
Mr = 991.05	Dx = 1.383 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9946 reflections
a = 14.9420 (9) Å	θ = 2.3–28.3°
b = 10.8718 (7) Å	µ = 0.24 mm−1
c = 16.0773 (10) Å	T = 150 K
β = 114.3270 (8)°	Plate, pale yellow
V = 2379.8 (3) Å3	0.23 × 0.19 × 0.05 mm
Z = 2

Bruker SMART APEX CCD diffractometer	5955 independent reflections
Radiation source: fine-focus sealed tube	4481 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
Detector resolution: 8.3660 pixels mm-1	θmax = 28.4°, θmin = 2.3°
φ and ω scans	h = −19→19
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −14→14
Tmin = 0.81, Tmax = 0.99	l = −21→21
41576 measured reflections

Refinement on F2	28 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.132	w = 1/[σ2(Fo2) + (0.0554P)2 + 1.6086P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
5955 reflections	Δρmax = 0.77 e Å−3
317 parameters	Δρmin = −0.62 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	Occ. (<1)
P1	0.57869 (4)	1.03372 (5)	0.46675 (4)	0.0305 (2)
O3	0.86773 (11)	0.62642 (14)	0.61933 (12)	0.0427 (5)
O4A	0.5173 (2)	1.0157 (3)	0.3725 (2)	0.0309 (5)	0.500
O4B	0.5512 (2)	1.0296 (3)	0.3642 (2)	0.0309 (5)	0.500
O5A	0.5998 (2)	1.1419 (3)	0.5154 (2)	0.0309 (5)	0.500
O5B	0.6358 (2)	1.1646 (3)	0.4900 (2)	0.0309 (5)	0.500
O6	0.52418 (18)	1.0374 (2)	0.53284 (18)	0.0274 (8)	0.500
C18	0.96967 (18)	0.6470 (3)	0.6554 (2)	0.0581 (10)
C19	0.80643 (15)	0.72531 (19)	0.58665 (14)	0.0316 (6)
C20	0.83752 (15)	0.8459 (2)	0.59149 (16)	0.0361 (6)
C21	0.76781 (15)	0.93886 (19)	0.55603 (15)	0.0346 (6)
C22	0.66850 (14)	0.91441 (18)	0.51714 (13)	0.0272 (5)
C23	0.63917 (15)	0.7916 (2)	0.51452 (15)	0.0344 (6)
C24	0.70699 (16)	0.69865 (19)	0.54824 (16)	0.0370 (7)
S1	0.58537 (4)	1.08926 (4)	0.08978 (3)	0.0289 (1)
O1	0.91131 (13)	1.09586 (18)	0.27696 (13)	0.0560 (7)
O2	0.87989 (13)	0.92245 (18)	0.33537 (13)	0.0570 (6)
N1	0.49957 (14)	0.85683 (15)	0.23756 (12)	0.0331 (5)
N2	0.75816 (16)	1.19991 (18)	0.13051 (15)	0.0400 (6)
C1	0.31772 (17)	0.8669 (2)	0.18867 (15)	0.0381 (7)
C2	0.29320 (18)	0.9500 (2)	0.24134 (16)	0.0423 (7)
C3	0.2121 (2)	1.0252 (3)	0.2017 (2)	0.0544 (10)
C4	0.1555 (2)	1.0191 (3)	0.1092 (2)	0.0628 (11)
C5	0.1785 (2)	0.9363 (3)	0.0564 (2)	0.0629 (10)
C6	0.25792 (19)	0.8596 (3)	0.09563 (17)	0.0501 (8)
C7	0.40835 (18)	0.7891 (2)	0.23008 (16)	0.0412 (7)
C8	0.48723 (16)	0.91160 (19)	0.14823 (14)	0.0331 (6)
C9	0.58213 (16)	0.96802 (17)	0.15942 (14)	0.0304 (6)
C10	0.67162 (16)	0.94260 (18)	0.22578 (14)	0.0323 (6)
C11	0.68191 (17)	0.8442 (2)	0.29481 (15)	0.0386 (7)
C12	0.58719 (18)	0.77301 (19)	0.27059 (15)	0.0399 (7)
C13	0.71049 (16)	1.11013 (18)	0.15399 (14)	0.0317 (6)
C14	0.74755 (16)	1.02343 (19)	0.22349 (14)	0.0330 (6)
C15	0.85221 (18)	1.0206 (2)	0.27950 (16)	0.0423 (7)
C16A	0.9874 (3)	0.9227 (4)	0.3882 (4)	0.0673 (10)	0.753 (5)
C17A	1.0074 (3)	0.8018 (4)	0.4371 (3)	0.0673 (10)	0.753 (5)
C17B	1.0233 (8)	0.8259 (10)	0.3766 (6)	0.0673 (10)	0.247 (5)
C16B	0.9693 (9)	0.8858 (11)	0.4036 (11)	0.0673 (10)	0.247 (5)
H18A	1.00440	0.56880	0.67590	0.0870*
H18B	0.98850	0.70380	0.70710	0.0870*
H18C	0.98720	0.68280	0.60810	0.0870*
H20	0.90560	0.86510	0.61870	0.0430*
H21	0.78940	1.02150	0.55880	0.0420*
H23	0.57110	0.77220	0.48900	0.0410*
H24	0.68560	0.61580	0.54520	0.0440*
H2	0.33250	0.95530	0.30510	0.0510*
H2N	0.7183 (19)	1.261 (3)	0.0898 (18)	0.0480*
H3N	0.816 (2)	1.207 (3)	0.1698 (18)	0.0480*
H4	0.10050	1.07210	0.08190	0.0750*
H3	0.19530	1.08130	0.23830	0.0650*
H1N	0.5116 (18)	0.919 (2)	0.2803 (17)	0.0400*
H7A	0.40010	0.71460	0.19220	0.0490*
H7B	0.41660	0.76230	0.29170	0.0490*
H8A	0.46820	0.84700	0.10060	0.0400*
H8B	0.43500	0.97490	0.12920	0.0400*
H11A	0.70120	0.88250	0.35560	0.0460*
H11B	0.73470	0.78670	0.29840	0.0460*
H12A	0.58000	0.71220	0.22240	0.0480*
H12B	0.59020	0.72750	0.32500	0.0480*
H16A	1.00820	0.99200	0.43200	0.0810*	0.753 (5)
H16B	1.02190	0.92850	0.34740	0.0810*	0.753 (5)
H17A	1.07800	0.79360	0.47450	0.1010*	0.753 (5)
H17B	0.98540	0.73480	0.39240	0.1010*	0.753 (5)
H17C	0.97190	0.79790	0.47650	0.1010*	0.753 (5)
H5	0.13940	0.93220	−0.00740	0.0750*
H6	0.27220	0.80100	0.05900	0.0600*
H16C	1.00540	0.96010	0.43580	0.0810*	0.247 (5)
H16D	0.95610	0.83530	0.44850	0.0810*	0.247 (5)
H17D	1.08390	0.80320	0.42890	0.1010*	0.247 (5)
H17E	1.03950	0.87620	0.33410	0.1010*	0.247 (5)
H17F	0.98900	0.75130	0.34540	0.1010*	0.247 (5)

	U11	U22	U33	U12	U13	U23
P1	0.0343 (3)	0.0305 (3)	0.0281 (3)	0.0102 (2)	0.0143 (2)	0.0061 (2)
O3	0.0398 (9)	0.0337 (8)	0.0528 (10)	0.0139 (7)	0.0172 (8)	0.0100 (7)
O4A	0.0354 (11)	0.0229 (7)	0.0312 (8)	0.0003 (8)	0.0104 (7)	0.0002 (6)
O4B	0.0354 (11)	0.0229 (7)	0.0312 (8)	0.0003 (8)	0.0104 (7)	0.0002 (6)
O5A	0.0354 (11)	0.0229 (7)	0.0312 (8)	0.0003 (8)	0.0104 (7)	0.0002 (6)
O5B	0.0354 (11)	0.0229 (7)	0.0312 (8)	0.0003 (8)	0.0104 (7)	0.0002 (6)
O6	0.0248 (13)	0.0284 (14)	0.0272 (13)	0.0006 (10)	0.0090 (11)	−0.0027 (11)
C18	0.0409 (14)	0.0554 (16)	0.076 (2)	0.0206 (12)	0.0220 (14)	0.0182 (14)
C19	0.0343 (10)	0.0285 (10)	0.0324 (10)	0.0085 (8)	0.0143 (9)	0.0052 (8)
C20	0.0260 (10)	0.0333 (11)	0.0446 (12)	0.0019 (8)	0.0101 (9)	−0.0016 (9)
C21	0.0338 (11)	0.0246 (9)	0.0425 (12)	−0.0002 (8)	0.0128 (9)	−0.0027 (9)
C22	0.0297 (9)	0.0261 (9)	0.0246 (9)	0.0036 (8)	0.0101 (8)	−0.0001 (7)
C23	0.0273 (10)	0.0327 (11)	0.0403 (12)	−0.0019 (8)	0.0110 (9)	0.0037 (9)
C24	0.0375 (11)	0.0256 (10)	0.0459 (13)	0.0000 (9)	0.0153 (10)	0.0073 (9)
S1	0.0363 (3)	0.0210 (2)	0.0283 (2)	0.0004 (2)	0.0121 (2)	0.0003 (2)
O1	0.0402 (10)	0.0589 (12)	0.0560 (12)	−0.0101 (9)	0.0069 (9)	−0.0114 (9)
O2	0.0447 (10)	0.0558 (11)	0.0514 (11)	0.0127 (8)	0.0006 (8)	0.0041 (9)
N1	0.0489 (11)	0.0207 (8)	0.0293 (9)	−0.0042 (7)	0.0156 (8)	0.0009 (7)
N2	0.0404 (11)	0.0345 (10)	0.0403 (11)	−0.0099 (9)	0.0117 (9)	−0.0042 (9)
C1	0.0497 (13)	0.0345 (11)	0.0335 (11)	−0.0167 (10)	0.0205 (10)	−0.0019 (9)
C2	0.0475 (13)	0.0459 (13)	0.0367 (12)	−0.0138 (11)	0.0206 (11)	−0.0036 (10)
C3	0.0537 (16)	0.0502 (15)	0.0687 (19)	−0.0110 (12)	0.0347 (15)	−0.0037 (13)
C4	0.0482 (16)	0.0642 (19)	0.074 (2)	−0.0049 (14)	0.0231 (15)	0.0188 (16)
C5	0.0553 (17)	0.082 (2)	0.0424 (15)	−0.0182 (16)	0.0111 (13)	0.0112 (15)
C6	0.0586 (16)	0.0548 (15)	0.0355 (12)	−0.0186 (13)	0.0181 (12)	−0.0054 (11)
C7	0.0596 (15)	0.0274 (10)	0.0388 (12)	−0.0115 (10)	0.0224 (11)	0.0014 (9)
C8	0.0439 (12)	0.0271 (10)	0.0276 (10)	−0.0048 (9)	0.0139 (9)	0.0024 (8)
C9	0.0416 (11)	0.0210 (9)	0.0282 (10)	0.0026 (8)	0.0139 (9)	0.0004 (8)
C10	0.0409 (11)	0.0232 (9)	0.0317 (10)	0.0060 (8)	0.0138 (9)	−0.0019 (8)
C11	0.0492 (13)	0.0290 (10)	0.0334 (11)	0.0087 (9)	0.0127 (10)	0.0053 (9)
C12	0.0596 (14)	0.0215 (9)	0.0351 (11)	0.0051 (9)	0.0161 (11)	0.0041 (9)
C13	0.0388 (11)	0.0239 (9)	0.0327 (11)	−0.0001 (8)	0.0149 (9)	−0.0076 (8)
C14	0.0378 (11)	0.0265 (10)	0.0318 (10)	0.0035 (8)	0.0115 (9)	−0.0059 (8)
C15	0.0428 (13)	0.0408 (13)	0.0361 (12)	0.0074 (10)	0.0090 (10)	−0.0073 (10)
C16A	0.0518 (16)	0.0641 (19)	0.0685 (19)	0.0069 (13)	0.0073 (13)	0.0263 (15)
C17A	0.0518 (16)	0.0641 (19)	0.0685 (19)	0.0069 (13)	0.0073 (13)	0.0263 (15)
C17B	0.0518 (16)	0.0641 (19)	0.0685 (19)	0.0069 (13)	0.0073 (13)	0.0263 (15)
C16B	0.0518 (16)	0.0641 (19)	0.0685 (19)	0.0069 (13)	0.0073 (13)	0.0263 (15)

S1—C9	1.743 (2)	C1—C6	1.393 (3)
S1—C13	1.739 (2)	C2—C3	1.381 (4)
P1—O4A	1.425 (3)	C3—C4	1.377 (4)
P1—O5B	1.622 (3)	C4—C5	1.375 (4)
P1—O6	1.583 (3)	C5—C6	1.373 (4)
P1—C22	1.801 (2)	C8—C9	1.486 (3)
P1—O6i	1.723 (3)	C9—C10	1.352 (3)
P1—O4B	1.527 (3)	C10—C11	1.503 (3)
P1—O5A	1.375 (3)	C10—C14	1.448 (3)
O3—C18	1.407 (4)	C11—C12	1.517 (4)
O3—C19	1.369 (3)	C13—C14	1.391 (3)
O5A—O6	1.705 (4)	C14—C15	1.448 (4)
O1—C15	1.217 (3)	C16A—C17A	1.497 (6)
O2—C16A	1.476 (6)	C16B—C17B	1.246 (19)
O2—C15	1.346 (3)	C2—H2	0.9500
O2—C16B	1.393 (16)	C3—H3	0.9500
N1—C8	1.494 (3)	C4—H4	0.9500
N1—C7	1.510 (3)	C5—H5	0.9500
N1—C12	1.501 (3)	C6—H6	0.9500
N2—C13	1.351 (3)	C7—H7A	0.9900
N1—H1N	0.93 (2)	C7—H7B	0.9900
N2—H2N	0.95 (3)	C8—H8A	0.9900
N2—H3N	0.84 (3)	C8—H8B	0.9900
C19—C20	1.382 (3)	C11—H11A	0.9900
C19—C24	1.385 (3)	C11—H11B	0.9900
C20—C21	1.394 (3)	C12—H12A	0.9900
C21—C22	1.378 (3)	C12—H12B	0.9900
C22—C23	1.401 (3)	C16A—H16A	0.9900
C23—C24	1.375 (3)	C16A—H16B	0.9900
C18—H18A	0.9800	C16B—H16C	0.9900
C18—H18B	0.9800	C16B—H16D	0.9900
C18—H18C	0.9800	C17A—H17C	0.9800
C20—H20	0.9500	C17A—H17A	0.9800
C21—H21	0.9500	C17A—H17B	0.9800
C23—H23	0.9500	C17B—H17D	0.9800
C24—H24	0.9500	C17B—H17E	0.9800
C1—C2	1.387 (3)	C17B—H17F	0.9800
C1—C7	1.500 (4)
C9—S1—C13	91.43 (11)	S1—C9—C8	120.79 (16)
O4A—P1—O5B	114.38 (17)	S1—C9—C10	112.42 (18)
O4A—P1—O6	115.68 (17)	C9—C10—C11	119.7 (2)
O4A—P1—O5A	128.22 (19)	C11—C10—C14	127.5 (2)
O4A—P1—O6i	75.99 (16)	C9—C10—C14	112.75 (19)
O4B—P1—O5A	122.41 (18)	C10—C11—C12	111.89 (19)
O4B—P1—O5B	99.01 (16)	N1—C12—C11	111.51 (17)
O4B—P1—O6	137.86 (16)	N2—C13—C14	129.3 (2)
O4B—P1—C22	106.48 (14)	S1—C13—C14	111.32 (17)
O4B—P1—O6i	98.48 (15)	S1—C13—N2	119.36 (17)
O5A—P1—O6	69.98 (16)	C10—C14—C13	112.0 (2)
O5A—P1—C22	113.97 (15)	C10—C14—C15	128.92 (19)
O5A—P1—O6i	112.18 (16)	C13—C14—C15	119.0 (2)
O5B—P1—O6	100.98 (14)	O1—C15—O2	121.9 (2)
O5B—P1—C22	107.72 (13)	O1—C15—C14	125.3 (2)
O5B—P1—O6i	141.12 (14)	O2—C15—C14	112.8 (2)
O6—P1—C22	102.14 (11)	O2—C16A—C17A	103.6 (4)
O4A—P1—C22	114.41 (15)	O2—C16B—C17B	115.1 (12)
O6i—P1—C22	100.12 (11)	C1—C2—H2	120.00
O6—P1—O6i	45.77 (13)	C3—C2—H2	120.00
C18—O3—C19	118.2 (2)	C2—C3—H3	120.00
P1—O5A—O6	60.75 (15)	C4—C3—H3	120.00
P1—O6—O5A	49.27 (13)	C3—C4—H4	120.00
P1—O6—P1i	134.23 (16)	C5—C4—H4	120.00
P1i—O6—O5A	162.2 (2)	C4—C5—H5	120.00
C15—O2—C16A	110.2 (3)	C6—C5—H5	120.00
C15—O2—C16B	133.2 (6)	C1—C6—H6	120.00
C8—N1—C12	109.04 (19)	C5—C6—H6	120.00
C7—N1—C8	111.58 (18)	N1—C7—H7A	109.00
C7—N1—C12	111.06 (17)	N1—C7—H7B	109.00
C8—N1—H1N	109.4 (15)	C1—C7—H7A	109.00
C12—N1—H1N	107.8 (17)	C1—C7—H7B	109.00
C7—N1—H1N	107.9 (18)	H7A—C7—H7B	108.00
C13—N2—H2N	116.4 (19)	N1—C8—H8A	110.00
C13—N2—H3N	111 (2)	N1—C8—H8B	110.00
H2N—N2—H3N	128 (3)	C9—C8—H8A	110.00
O3—C19—C20	124.5 (2)	C9—C8—H8B	110.00
O3—C19—C24	115.60 (19)	H8A—C8—H8B	108.00
C20—C19—C24	119.8 (2)	C10—C11—H11A	109.00
C19—C20—C21	119.2 (2)	C10—C11—H11B	109.00
C20—C21—C22	122.0 (2)	C12—C11—H11A	109.00
P1—C22—C23	120.47 (17)	C12—C11—H11B	109.00
P1—C22—C21	121.92 (16)	H11A—C11—H11B	108.00
C21—C22—C23	117.56 (19)	N1—C12—H12A	109.00
C22—C23—C24	121.2 (2)	N1—C12—H12B	109.00
C19—C24—C23	120.2 (2)	C11—C12—H12A	109.00
O3—C18—H18B	110.00	C11—C12—H12B	109.00
O3—C18—H18C	109.00	H12A—C12—H12B	108.00
H18A—C18—H18B	110.00	O2—C16A—H16A	111.00
O3—C18—H18A	110.00	O2—C16A—H16B	111.00
H18A—C18—H18C	109.00	C17A—C16A—H16A	111.00
H18B—C18—H18C	109.00	C17A—C16A—H16B	111.00
C21—C20—H20	120.00	H16A—C16A—H16B	109.00
C19—C20—H20	120.00	O2—C16B—H16D	109.00
C20—C21—H21	119.00	C17B—C16B—H16C	108.00
C22—C21—H21	119.00	C17B—C16B—H16D	108.00
C24—C23—H23	119.00	H16C—C16B—H16D	107.00
C22—C23—H23	119.00	O2—C16B—H16C	109.00
C23—C24—H24	120.00	H17A—C17A—H17C	109.00
C19—C24—H24	120.00	H17B—C17A—H17C	110.00
C2—C1—C6	118.6 (2)	C16A—C17A—H17A	109.00
C6—C1—C7	120.5 (2)	C16A—C17A—H17B	109.00
C2—C1—C7	120.9 (2)	C16A—C17A—H17C	109.00
C1—C2—C3	120.4 (2)	H17A—C17A—H17B	109.00
C2—C3—C4	120.1 (3)	C16B—C17B—H17D	110.00
C3—C4—C5	120.0 (3)	C16B—C17B—H17E	109.00
C4—C5—C6	120.2 (3)	C16B—C17B—H17F	109.00
C1—C6—C5	120.6 (3)	H17D—C17B—H17E	109.00
N1—C7—C1	112.38 (18)	H17D—C17B—H17F	110.00
N1—C8—C9	108.32 (18)	H17E—C17B—H17F	109.00
C8—C9—C10	126.54 (19)
C13—S1—C9—C10	−1.85 (18)	C7—N1—C8—C9	−175.70 (17)
C13—S1—C9—C8	172.78 (18)	C8—N1—C12—C11	67.0 (2)
C9—S1—C13—C14	2.30 (17)	C12—N1—C7—C1	−174.44 (18)
C9—S1—C13—N2	−179.77 (19)	C8—N1—C7—C1	−52.6 (2)
C22—P1—O5A—O6	−94.76 (15)	O3—C19—C24—C23	179.1 (2)
O5B—P1—O5A—O6	−179.4 (4)	C24—C19—C20—C21	−1.1 (3)
O4B—P1—O6—O5A	−116.6 (2)	C20—C19—C24—C23	0.3 (3)
O6i—P1—O5A—O6	18.13 (17)	O3—C19—C20—C21	−179.7 (2)
O4A—P1—O6—O5A	−123.7 (2)	C19—C20—C21—C22	0.8 (3)
O6i—P1—O6—O5A	−156.3 (2)	C20—C21—C22—P1	−177.16 (18)
O4A—P1—O6—P1i	32.6 (3)	C20—C21—C22—C23	0.2 (3)
O4B—P1—O6—P1i	39.7 (3)	C21—C22—C23—C24	−1.0 (3)
O5A—P1—O6—P1i	156.3 (3)	P1—C22—C23—C24	176.45 (18)
O5B—P1—O6—P1i	156.6 (2)	C22—C23—C24—C19	0.7 (3)
O5B—P1—O6—O5A	0.31 (19)	C7—C1—C6—C5	−175.7 (3)
C22—P1—O6—O5A	111.34 (16)	C2—C1—C7—N1	−82.4 (3)
O4B—P1—O5A—O6	134.7 (2)	C7—C1—C2—C3	177.0 (3)
O4Bi—P1i—O6—P1	154.3 (2)	C6—C1—C7—N1	95.7 (3)
O5Ai—P1i—O6—P1	24.1 (3)	C2—C1—C6—C5	2.4 (4)
O5Bi—P1i—O6—P1	38.4 (3)	C6—C1—C2—C3	−1.1 (4)
O6i—P1i—O6—P1	0.02 (18)	C1—C2—C3—C4	−0.7 (4)
C22i—P1i—O6—P1	−97.2 (2)	C2—C3—C4—C5	1.3 (5)
O4A—P1—C22—C23	−56.9 (2)	C3—C4—C5—C6	−0.1 (5)
O4B—P1—C22—C23	−79.8 (2)	C4—C5—C6—C1	−1.8 (5)
O5A—P1—C22—C23	142.2 (2)	N1—C8—C9—S1	−153.96 (15)
O5B—P1—C22—C23	174.75 (19)	N1—C8—C9—C10	19.9 (3)
O6—P1—C22—C23	68.9 (2)	S1—C9—C10—C11	177.33 (16)
O6i—P1—C22—C23	22.2 (2)	S1—C9—C10—C14	0.9 (2)
O6—P1—C22—C21	−113.8 (2)	C8—C9—C10—C11	3.1 (3)
O6i—P1—C22—C21	−160.46 (19)	C8—C9—C10—C14	−173.3 (2)
O5A—P1—C22—C21	−40.5 (2)	C9—C10—C11—C12	8.0 (3)
O4Ai—P1i—O6—P1	150.0 (3)	C14—C10—C11—C12	−176.1 (2)
O4B—P1—C22—C21	97.5 (2)	C9—C10—C14—C13	0.8 (3)
C22—P1—O6—P1i	−92.4 (2)	C9—C10—C14—C15	−176.2 (2)
O5B—P1—C22—C21	−7.9 (2)	C11—C10—C14—C13	−175.2 (2)
O4A—P1—O5A—O6	107.5 (2)	C11—C10—C14—C15	7.8 (4)
O4A—P1—C22—C21	120.4 (2)	C10—C11—C12—N1	−42.3 (3)
O6i—P1—O6—P1i	0.00 (16)	S1—C13—C14—C10	−2.2 (2)
C18—O3—C19—C24	177.2 (2)	N2—C13—C14—C15	−2.5 (4)
C18—O3—C19—C20	−4.1 (3)	S1—C13—C14—C15	175.15 (17)
C16A—O2—C15—O1	−0.6 (4)	N2—C13—C14—C10	−179.9 (2)
C16A—O2—C15—C14	178.1 (3)	C10—C14—C15—O1	−175.9 (2)
C15—O2—C16A—C17A	−173.1 (3)	C10—C14—C15—O2	5.5 (3)
C7—N1—C12—C11	−169.64 (18)	C13—C14—C15—O1	7.3 (4)
C12—N1—C8—C9	−52.7 (2)	C13—C14—C15—O2	−171.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O4A	0.93 (2)	1.79 (3)	2.699 (4)	165 (2)
N1—H1N···O4B	0.93 (2)	1.72 (2)	2.641 (4)	171 (2)
N2—H2N···O5Aii	0.95 (3)	1.98 (3)	2.894 (4)	160 (3)
N2—H2N···O5Bii	0.95 (3)	1.77 (3)	2.686 (4)	162 (3)
N2—H3N···O1	0.84 (3)	2.11 (3)	2.761 (3)	135 (3)
C6—H6···O5Biii	0.95	2.37	3.273 (4)	159
C7—H7A···O4Biii	0.99	2.44	3.373 (4)	157
C7—H7B···S1iii	0.99	2.69	3.591 (2)	152
C8—H8A···O5Biii	0.99	2.57	3.488 (4)	154
C18—H18B···O1iv	0.98	2.60	3.251 (4)	124
C20—H20···O1iv	0.95	2.59	3.524 (3)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O4A	0.93 (2)	1.79 (3)	2.699 (4)	165 (2)
N1—H1N⋯O4B	0.93 (2)	1.72 (2)	2.641 (4)	171 (2)
N2—H2N⋯O5A i	0.95 (3)	1.98 (3)	2.894 (4)	160 (3)
N2—H2N⋯O5B i	0.95 (3)	1.77 (3)	2.686 (4)	162 (3)
N2—H3N⋯O1	0.84 (3)	2.11 (3)	2.761 (3)	135 (3)
C6—H6⋯O5B ii	0.95	2.37	3.273 (4)	159
C7—H7A⋯O4B ii	0.99	2.44	3.373 (4)	157
C7—H7B⋯S1ii	0.99	2.69	3.591 (2)	152
C8—H8A⋯O5B ii	0.99	2.57	3.488 (4)	154
C18—H18B⋯O1iii	0.98	2.60	3.251 (4)	124
C20—H20⋯O1iii	0.95	2.59	3.524 (3)	168

Symmetry codes: (i) ; (ii) ; (iii) .