Tetra­aqua­bis(1,3-di-4-pyridylpropane-κN)cobalt(II) bis­(4-aminona­phthalene-1-sulfonate)

The Co^II atom in the crystal structure of the title compound, [Co(C₁₃H₁₄N₂)₂(H₂O)₄](C₁₀H₈NO₃S)₂, lies on a center of inversion in an N₂O₄ octa­hedron. The sulfonate anion inter­acts with the cation through hydrogen bonds, giving rise to a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.031
• wR factor = 0.089
• Data-to-parameter ratio = 16.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          4
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co1    -   N1      ..       5.05 su

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Co1         (2)       1.83
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          6

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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S1. Comment

Among metal sulfonates, some have the sulfonate anion directly bonded to the metal center whereas other have the anion in an outer-sphere type of coordination, the anion interacting indirectly through hydrogen bonds (Cai, 2004). The few metal 4-amino-naphthalenesulfonates that have been identified by crystallography show this feature (Li et al., 2005; Li et al., 2006; Zhou et al., 2005). The cobalt(II) atom in the title compound lies on a center-of-inversion in an N₂O₄ octahedron (see Table 1). The sulfonate anion interacts with the cation through hydrogen bonds (see Table 2), these giving rise to a three-dimensional network,

Related literature

For a crystallographic review of metal arenesulfonates, see Cai (2004). For examples of metal 4-amino-naphthalenesulfonates in which the anion is not directly bonded to the metal, see Li et al. (2006) and Zhou et al. (2005) for the cadmium salts, and Li et al. (2005) for the copper salt.

S2. Experimental

To cobalt(II) nitrate (1 mmol) dissolved in water was sodium 4-amino-naphthalene sulfonate (1 mmol) dissolved in methanol. 1,3-Bis(4-pyridyl)propane (1 mmol) dissolved in methanol was then added. Large red crystals separated from the solution after several days (in 80% yield).

S3. Refinement

The water and amino H-atoms were located in a difference Fourier map, and were refined with a distance restraint of O–H = N–H = 0.85±0.01 Å; their displacement parameters were freely refined. The carbon-bound H-atoms were generated geometrically (C–H 0.93 to 0.97 Å); they were included in the refinement in the riding model approximation, with U(H) set to 1.2U_eq(C).

Computing details

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures

Fig. 1. Thermal ellipsoid plot depicting the coordination geometry of cobalt; displacement ellipsoids are drawn at the 70% probability level, and H atoms as spheres of arbitrary radius.[Symmetry code (i): 1 – x, 1 – y, 1 - z.]

Tetraaquabis(1,3-di-4-pyridylpropane-κN)cobalt(II) bis(4-aminonaphthalene-1-sulfonate)

Crystal data

[Co(C13H14N2)2(H2O)4](C10H8NO3S)2	F(000) = 1018
Mr = 971.99	Dx = 1.365 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 743 reflections
a = 9.7790 (6) Å	θ = 2.5–28.2°
b = 16.261 (1) Å	µ = 0.51 mm^−1
c = 15.375 (1) Å	T = 295 K
β = 104.625 (1)°	Block, red
V = 2365.6 (3) Å^3	0.42 × 0.31 × 0.26 mm
Z = 2

Data collection

Bruker APEX II area-detector diffractometer	5383 independent reflections
Radiation source: fine-focus sealed tube	4524 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
φ and ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→12
Tmin = 0.759, Tmax = 0.878	k = −21→21
16557 measured reflections	l = −18→19

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0499P)^2 + 0.4354P] where P = (Fo^2 + 2Fc^2)/3
5383 reflections	(Δ/σ)max = 0.001
319 parameters	Δρmax = 0.27 e Å^−3
6 restraints	Δρmin = −0.31 e Å^−3

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

	x	y	z	Uiso*/Ueq
Co1	0.5000	0.5000	0.5000	0.03216 (9)
S1	0.04035 (4)	0.59566 (2)	0.64502 (2)	0.04044 (11)
O1	0.17834 (13)	0.56048 (8)	0.64976 (8)	0.0567 (3)
O2	−0.02305 (14)	0.63540 (8)	0.55948 (8)	0.0586 (3)
O3	−0.05603 (13)	0.53643 (8)	0.66932 (8)	0.0535 (3)
O1W	0.35327 (13)	0.58214 (8)	0.53205 (8)	0.0472 (3)
H11	0.2855 (17)	0.5976 (12)	0.4894 (11)	0.067 (6)*
H12	0.315 (2)	0.5725 (13)	0.5741 (11)	0.067 (6)*
O2W	0.65302 (13)	0.55626 (8)	0.60223 (7)	0.0481 (3)
H21	0.7406 (11)	0.5579 (13)	0.6092 (14)	0.063 (6)*
H22	0.640 (2)	0.5608 (14)	0.6540 (8)	0.077 (7)*
N1	0.53869 (13)	0.58325 (8)	0.39844 (8)	0.0360 (3)
N2	0.62516 (18)	0.57641 (11)	−0.22209 (10)	0.0620 (4)
N3	0.10056 (15)	0.87085 (8)	0.90985 (9)	0.0418 (3)
H31	0.0643 (17)	0.8627 (10)	0.9540 (9)	0.042 (5)*
H32	0.0650 (18)	0.9146 (8)	0.8821 (11)	0.046 (5)*
C1	0.43213 (18)	0.61539 (11)	0.33443 (11)	0.0466 (4)
H1	0.3400	0.6053	0.3379	0.056*
C2	0.45187 (19)	0.66237 (11)	0.26416 (11)	0.0498 (4)
H2	0.3744	0.6838	0.2222	0.060*
C3	0.58785 (19)	0.67768 (10)	0.25596 (10)	0.0440 (4)
C4	0.69713 (18)	0.64612 (10)	0.32255 (11)	0.0473 (4)
H4	0.7901	0.6556	0.3207	0.057*
C5	0.66959 (17)	0.60054 (10)	0.39194 (10)	0.0412 (3)
H5	0.7457	0.5809	0.4363	0.049*
C6	0.6135 (2)	0.72465 (11)	0.17690 (11)	0.0547 (4)
H6A	0.7018	0.7546	0.1959	0.066*
H6B	0.5383	0.7645	0.1568	0.066*
C7	0.6199 (2)	0.66793 (10)	0.09830 (10)	0.0502 (4)
H7A	0.6977	0.6296	0.1174	0.060*
H7B	0.5331	0.6364	0.0805	0.060*
C8	0.6399 (2)	0.71753 (11)	0.01797 (11)	0.0559 (4)
H8A	0.5661	0.7588	0.0026	0.067*
H8B	0.7298	0.7460	0.0352	0.067*
C9	0.5088 (2)	0.59422 (16)	−0.19520 (14)	0.0721 (6)
H9	0.4222	0.5763	−0.2304	0.086*
C10	0.5104 (2)	0.63766 (15)	−0.11825 (13)	0.0639 (5)
H10	0.4261	0.6482	−0.1027	0.077*
C11	0.63622 (19)	0.66574 (11)	−0.06400 (10)	0.0473 (4)
C12	0.75670 (19)	0.64531 (13)	−0.09045 (11)	0.0563 (5)
H121	0.8449	0.6610	−0.0554	0.068*
C13	0.7465 (2)	0.60173 (13)	−0.16871 (13)	0.0609 (5)
H13	0.8295	0.5894	−0.1850	0.073*
C14	0.06477 (15)	0.67457 (9)	0.72696 (9)	0.0347 (3)
C15	0.03967 (16)	0.75405 (9)	0.69763 (10)	0.0402 (3)
H15	0.0136	0.7648	0.6362	0.048*
C16	0.05262 (17)	0.81950 (9)	0.75851 (10)	0.0408 (3)
H16	0.0368	0.8730	0.7370	0.049*
C17	0.08839 (15)	0.80554 (8)	0.84941 (9)	0.0342 (3)
C18	0.11955 (15)	0.72344 (8)	0.88304 (9)	0.0338 (3)
C19	0.16225 (18)	0.70681 (10)	0.97662 (10)	0.0454 (4)
H19	0.1718	0.7500	1.0174	0.054*
C20	0.1896 (2)	0.62808 (11)	1.00766 (12)	0.0574 (5)
H20	0.2157	0.6180	1.0692	0.069*
C21	0.1782 (2)	0.56277 (11)	0.94689 (13)	0.0579 (5)
H211	0.1973	0.5095	0.9685	0.069*
C22	0.13945 (18)	0.57630 (10)	0.85632 (11)	0.0465 (4)
H221	0.1335	0.5322	0.8171	0.056*
C23	0.10801 (15)	0.65683 (9)	0.82121 (9)	0.0343 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.02968 (15)	0.04245 (16)	0.02514 (13)	0.00390 (11)	0.00836 (10)	0.00034 (10)
S1	0.0375 (2)	0.0465 (2)	0.0397 (2)	−0.00494 (16)	0.01423 (16)	−0.01240 (15)
O1	0.0469 (7)	0.0694 (8)	0.0596 (7)	0.0074 (6)	0.0247 (6)	−0.0138 (6)
O2	0.0647 (8)	0.0700 (8)	0.0381 (6)	−0.0011 (7)	0.0075 (6)	−0.0122 (5)
O3	0.0531 (7)	0.0504 (7)	0.0613 (7)	−0.0169 (6)	0.0224 (6)	−0.0178 (6)
O1W	0.0430 (7)	0.0627 (7)	0.0386 (6)	0.0179 (5)	0.0151 (5)	0.0059 (5)
O2W	0.0384 (7)	0.0732 (8)	0.0326 (6)	−0.0061 (6)	0.0085 (5)	−0.0093 (5)
N1	0.0342 (6)	0.0458 (7)	0.0290 (6)	0.0041 (5)	0.0096 (5)	0.0005 (5)
N2	0.0634 (10)	0.0840 (11)	0.0420 (8)	−0.0129 (9)	0.0198 (7)	−0.0087 (7)
N3	0.0493 (8)	0.0349 (7)	0.0418 (7)	−0.0032 (6)	0.0127 (6)	−0.0047 (5)
C1	0.0368 (8)	0.0635 (10)	0.0404 (8)	0.0056 (7)	0.0116 (7)	0.0089 (7)
C2	0.0489 (10)	0.0612 (10)	0.0375 (8)	0.0078 (8)	0.0074 (7)	0.0107 (7)
C3	0.0601 (10)	0.0413 (8)	0.0349 (7)	−0.0015 (7)	0.0199 (7)	−0.0023 (6)
C4	0.0429 (9)	0.0555 (9)	0.0479 (9)	−0.0028 (7)	0.0198 (7)	0.0008 (7)
C5	0.0358 (8)	0.0499 (9)	0.0382 (8)	0.0022 (7)	0.0098 (6)	0.0014 (6)
C6	0.0803 (13)	0.0478 (9)	0.0426 (9)	−0.0027 (9)	0.0276 (9)	0.0034 (7)
C7	0.0684 (12)	0.0492 (9)	0.0370 (8)	−0.0014 (8)	0.0209 (8)	0.0042 (6)
C8	0.0754 (13)	0.0560 (10)	0.0405 (8)	−0.0084 (9)	0.0228 (8)	0.0040 (7)
C9	0.0514 (12)	0.1150 (18)	0.0483 (11)	−0.0213 (12)	0.0099 (9)	−0.0140 (11)
C10	0.0437 (10)	0.1006 (16)	0.0516 (10)	−0.0075 (10)	0.0195 (8)	−0.0068 (10)
C11	0.0537 (10)	0.0561 (9)	0.0335 (7)	−0.0064 (8)	0.0137 (7)	0.0089 (6)
C12	0.0427 (9)	0.0831 (13)	0.0414 (9)	−0.0087 (9)	0.0075 (7)	0.0015 (8)
C13	0.0491 (11)	0.0883 (14)	0.0495 (10)	−0.0010 (10)	0.0206 (8)	−0.0010 (9)
C14	0.0304 (7)	0.0391 (7)	0.0359 (7)	−0.0036 (6)	0.0106 (6)	−0.0053 (5)
C15	0.0420 (8)	0.0457 (8)	0.0326 (7)	−0.0018 (7)	0.0086 (6)	0.0006 (6)
C16	0.0460 (9)	0.0348 (7)	0.0410 (8)	0.0015 (6)	0.0099 (7)	0.0035 (6)
C17	0.0297 (7)	0.0347 (7)	0.0386 (7)	−0.0042 (5)	0.0093 (6)	−0.0039 (5)
C18	0.0292 (7)	0.0371 (7)	0.0348 (7)	−0.0027 (6)	0.0078 (6)	−0.0006 (5)
C19	0.0495 (9)	0.0483 (9)	0.0367 (8)	−0.0007 (7)	0.0078 (7)	−0.0017 (6)
C20	0.0719 (13)	0.0576 (10)	0.0395 (9)	0.0064 (9)	0.0083 (8)	0.0104 (7)
C21	0.0728 (13)	0.0425 (9)	0.0567 (10)	0.0083 (9)	0.0134 (9)	0.0134 (7)
C22	0.0519 (10)	0.0356 (8)	0.0518 (9)	0.0014 (7)	0.0129 (8)	−0.0008 (6)
C23	0.0294 (7)	0.0362 (7)	0.0378 (7)	−0.0021 (6)	0.0095 (6)	−0.0015 (5)

Geometric parameters (Å, º)

Co1—O1w	2.108 (1)	C6—H6B	0.9700
Co1—O2w	2.088 (1)	C7—C8	1.528 (2)
Co1—N1	2.171 (1)	C7—H7A	0.9700
Co1—O2w^i	2.088 (1)	C7—H7B	0.9700
Co1—O1w^i	2.108 (1)	C8—C11	1.509 (2)
Co1—N1^i	2.171 (1)	C8—H8A	0.9700
S1—O1	1.4504 (12)	C8—H8B	0.9700
S1—O2	1.4560 (13)	C9—C10	1.375 (3)
S1—O3	1.4606 (12)	C9—H9	0.9300
S1—C14	1.7717 (14)	C10—C11	1.378 (3)
O1W—H11	0.84 (1)	C10—H10	0.9300
O1W—H12	0.84 (1)	C11—C12	1.380 (2)
O2W—H21	0.84 (1)	C12—C13	1.378 (3)
O2W—H22	0.84 (1)	C12—H121	0.9300
N1—C5	1.339 (2)	C13—H13	0.9300
N1—C1	1.345 (2)	C14—C15	1.370 (2)
N2—C13	1.326 (3)	C14—C23	1.4327 (19)
N2—C9	1.337 (3)	C15—C16	1.402 (2)
N3—C17	1.3962 (18)	C15—H15	0.9300
N3—H31	0.85 (1)	C16—C17	1.371 (2)
N3—H32	0.86 (1)	C16—H16	0.9300
C1—C2	1.376 (2)	C17—C18	1.4363 (19)
C1—H1	0.9300	C18—C19	1.419 (2)
C2—C3	1.390 (2)	C18—C23	1.4266 (19)
C2—H2	0.9300	C19—C20	1.369 (2)
C3—C4	1.379 (2)	C19—H19	0.9300
C3—C6	1.509 (2)	C20—C21	1.400 (3)
C4—C5	1.380 (2)	C20—H20	0.9300
C4—H4	0.9300	C21—C22	1.365 (2)
C5—H5	0.9300	C21—H211	0.9300
C6—C7	1.534 (2)	C22—C23	1.420 (2)
C6—H6A	0.9700	C22—H221	0.9300
O2W^i—Co1—O2W	180.0	C8—C7—H7A	109.4
O2W^i—Co1—O1W	93.03 (5)	C6—C7—H7A	109.4
O2W—Co1—O1W	86.97 (5)	C8—C7—H7B	109.4
O2W^i—Co1—O1W^i	86.97 (5)	C6—C7—H7B	109.4
O2W—Co1—O1W^i	93.03 (5)	H7A—C7—H7B	108.0
O1W—Co1—O1W^i	180.0	C11—C8—C7	113.56 (14)
O2W^i—Co1—N1	87.34 (5)	C11—C8—H8A	108.9
O2W—Co1—N1	92.66 (5)	C7—C8—H8A	108.9
O1W—Co1—N1	91.47 (5)	C11—C8—H8B	108.9
O1W^i—Co1—N1	88.53 (5)	C7—C8—H8B	108.9
O2W^i—Co1—N1^i	92.66 (5)	H8A—C8—H8B	107.7
O2W—Co1—N1^i	87.34 (5)	N2—C9—C10	123.52 (19)
O1W—Co1—N1^i	88.53 (5)	N2—C9—H9	118.2
O1W^i—Co1—N1^i	91.47 (5)	C10—C9—H9	118.2
N1—Co1—N1^i	180.00 (5)	C9—C10—C11	120.34 (18)
O1—S1—O2	113.51 (8)	C9—C10—H10	119.8
O1—S1—O3	112.29 (8)	C11—C10—H10	119.8
O2—S1—O3	111.63 (8)	C10—C11—C12	116.10 (16)
O1—S1—C14	107.05 (7)	C10—C11—C8	121.30 (17)
O2—S1—C14	105.73 (7)	C12—C11—C8	122.58 (16)
O3—S1—C14	105.99 (7)	C13—C12—C11	120.13 (17)
Co1—O1W—H11	117.0 (15)	C13—C12—H121	119.9
Co1—O1W—H12	121.5 (15)	C11—C12—H121	119.9
H11—O1W—H12	104 (2)	N2—C13—C12	123.77 (18)
Co1—O2W—H21	128.8 (14)	N2—C13—H13	118.1
Co1—O2W—H22	120.1 (16)	C12—C13—H13	118.1
H21—O2W—H22	106 (2)	C15—C14—C23	120.35 (13)
C5—N1—C1	116.26 (13)	C15—C14—S1	117.93 (11)
C5—N1—Co1	121.89 (10)	C23—C14—S1	121.72 (11)
C1—N1—Co1	121.67 (11)	C14—C15—C16	121.19 (13)
C13—N2—C9	116.09 (17)	C14—C15—H15	119.4
C17—N3—H31	115.5 (12)	C16—C15—H15	119.4
C17—N3—H32	110.1 (12)	C17—C16—C15	120.77 (14)
H31—N3—H32	109 (2)	C17—C16—H16	119.6
N1—C1—C2	123.62 (16)	C15—C16—H16	119.6
N1—C1—H1	118.2	C16—C17—N3	120.62 (13)
C2—C1—H1	118.2	C16—C17—C18	119.81 (13)
C1—C2—C3	119.86 (15)	N3—C17—C18	119.52 (13)
C1—C2—H2	120.1	C19—C18—C23	118.97 (13)
C3—C2—H2	120.1	C19—C18—C17	121.56 (13)
C4—C3—C2	116.49 (14)	C23—C18—C17	119.47 (12)
C4—C3—C6	122.09 (16)	C20—C19—C18	120.87 (15)
C2—C3—C6	121.40 (16)	C20—C19—H19	119.6
C3—C4—C5	120.52 (15)	C18—C19—H19	119.6
C3—C4—H4	119.7	C19—C20—C21	120.07 (16)
C5—C4—H4	119.7	C19—C20—H20	120.0
N1—C5—C4	123.18 (14)	C21—C20—H20	120.0
N1—C5—H5	118.4	C22—C21—C20	120.87 (16)
C4—C5—H5	118.4	C22—C21—H211	119.6
C3—C6—C7	112.23 (13)	C20—C21—H211	119.6
C3—C6—H6A	109.2	C21—C22—C23	120.91 (15)
C7—C6—H6A	109.2	C21—C22—H221	119.5
C3—C6—H6B	109.2	C23—C22—H221	119.5
C7—C6—H6B	109.2	C22—C23—C18	118.28 (13)
H6A—C6—H6B	107.9	C22—C23—C14	123.39 (13)
C8—C7—C6	110.99 (14)	C18—C23—C14	118.33 (12)
O2W^i—Co1—N1—C5	−132.91 (12)	C11—C12—C13—N2	−0.6 (3)
O2W—Co1—N1—C5	47.09 (12)	O1—S1—C14—C15	113.60 (13)
O1W—Co1—N1—C5	134.13 (12)	O2—S1—C14—C15	−7.73 (14)
O1W^i—Co1—N1—C5	−45.87 (12)	O3—S1—C14—C15	−126.36 (13)
O2W^i—Co1—N1—C1	42.01 (12)	O1—S1—C14—C23	−67.00 (13)
O2W—Co1—N1—C1	−137.99 (12)	O2—S1—C14—C23	171.67 (12)
O1W—Co1—N1—C1	−50.96 (13)	O3—S1—C14—C23	53.04 (14)
O1W^i—Co1—N1—C1	129.04 (13)	C23—C14—C15—C16	−1.3 (2)
C5—N1—C1—C2	1.2 (2)	S1—C14—C15—C16	178.07 (12)
Co1—N1—C1—C2	−173.96 (13)	C14—C15—C16—C17	−1.2 (2)
N1—C1—C2—C3	1.0 (3)	C15—C16—C17—N3	−179.70 (14)
C1—C2—C3—C4	−2.2 (2)	C15—C16—C17—C18	3.0 (2)
C1—C2—C3—C6	176.33 (16)	C16—C17—C18—C19	177.55 (15)
C2—C3—C4—C5	1.2 (2)	N3—C17—C18—C19	0.2 (2)
C6—C3—C4—C5	−177.29 (15)	C16—C17—C18—C23	−2.2 (2)
C1—N1—C5—C4	−2.3 (2)	N3—C17—C18—C23	−179.58 (13)
Co1—N1—C5—C4	172.91 (12)	C23—C18—C19—C20	−1.2 (2)
C3—C4—C5—N1	1.1 (2)	C17—C18—C19—C20	179.03 (16)
C4—C3—C6—C7	88.7 (2)	C18—C19—C20—C21	1.2 (3)
C2—C3—C6—C7	−89.8 (2)	C19—C20—C21—C22	−0.3 (3)
C3—C6—C7—C8	177.69 (17)	C20—C21—C22—C23	−0.7 (3)
C6—C7—C8—C11	−175.75 (17)	C21—C22—C23—C18	0.7 (2)
C13—N2—C9—C10	1.4 (3)	C21—C22—C23—C14	−179.02 (16)
N2—C9—C10—C11	0.2 (4)	C19—C18—C23—C22	0.2 (2)
C9—C10—C11—C12	−1.9 (3)	C17—C18—C23—C22	180.00 (14)
C9—C10—C11—C8	176.58 (19)	C19—C18—C23—C14	179.99 (14)
C7—C8—C11—C10	77.4 (2)	C17—C18—C23—C14	−0.3 (2)
C7—C8—C11—C12	−104.1 (2)	C15—C14—C23—C22	−178.26 (15)
C10—C11—C12—C13	2.1 (3)	S1—C14—C23—C22	2.4 (2)
C8—C11—C12—C13	−176.35 (17)	C15—C14—C23—C18	2.0 (2)
C9—N2—C13—C12	−1.2 (3)	S1—C14—C23—C18	−177.38 (10)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H12···O1	0.84 (1)	1.99 (1)	2.809 (1)	164 (2)
O1W—H11···N3^ii	0.84 (1)	1.98 (1)	2.807 (2)	167 (2)
O2W—H21···O3^iii	0.84 (1)	2.00 (1)	2.790 (2)	157 (2)
O2W—H22···N2^iv	0.84 (1)	1.96 (1)	2.802 (2)	175 (2)
N3—H31···O2^v	0.85 (1)	2.01 (1)	2.858 (2)	170 (2)
N3—H32···O3^vi	0.86 (1)	2.13 (1)	2.942 (2)	159 (2)

Symmetry codes: (ii) x, −y+3/2, z−1/2; (iii) x+1, y, z; (iv) x, y, z+1; (v) x, −y+3/2, z+1/2; (vi) −x, y+1/2, −z+3/2.