trans-Tetra-aqua-bis{(E)-2-cyano-1-[(ethoxy-carbon-yl)methyl-sulfan-yl]-2-(1-naphthyl-amino-carbon-yl)ethene-1-thiol-ato}calcium(II) diethyl ether disolvate.

In the title compound, [Ca(C(18)H(15)N(2)O(3)S(2))(H(2)O)(4)]·2C(4)H(10)O, the Ca atom, which lies on an inversion centre, is coordinated octa-hedrally by four water mol-ecules and two anions of the ketene dithio-acetal, the donor atoms of which are the amidic carbonyl O atoms. The central backbone of the ligands (excluding the naphthalene and oxoethyl groups) is essentially planar (r.m.s. deviation 0.035 Å). Intra-molecular hydrogen bonds are observed from the NH group to the formally 'thiol-ate' S atom and from one coordinated water to the nitrile group and to the ether O atom. Inter-molecular hydrogen bonds from the second independent water mol-ecule to the thiol-ate S atom and the side-chain oxo group connect the mol-ecules in chains parallel to the a axis.

Related literature

For our studies exploring the synthetic potential of ketene dithioacetals for synthesizing new classes of novel antimetabolic agents, see: Elgemeie & Sood (2006 ▶); Elgemeie et al. (2008 ▶, 2009 ▶). For our reports of successful approaches for the synthesis of mercaptopurine and pyrimidine analogues by the reaction of ketene dithioacetals with active methylene functions, see: Elgemeie (2003 ▶); Elgemeie et al. (2004 ▶, 2007 ▶).

Experimental

Crystal data

[Ca(C18H15N2O3S2)(H2O)4]·2C4H10O

M = 1003.26

Triclinic,

a = 7.8665 (3) Å

b = 12.4361 (5) Å

c = 13.8045 (6) Å

α = 103.692 (4)°

β = 99.963 (4)°

γ = 101.609 (3)°

V = 1250.24 (9) Å3

Z = 1

Mo Kα radiation

μ = 0.35 mm−1

T = 100 K

0.4 × 0.3 × 0.1 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.970, T max = 1.000

26853 measured reflections

6443 independent reflections

4941 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.070

S = 0.96

6443 reflections

326 parameters

18 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Siemens, 1994 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810013024/bt5223sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013024/bt5223Isup2.hkl

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

[Ca(C18H15N2O3S2)(H2O)4]·2C4H10O	F(000) = 530
Mr = 1003.26	Dx = 1.333 Mg m−3
Triclinic, P1	Melting point = 479–481 K
a = 7.8665 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.4361 (5) Å	Cell parameters from 11577 reflections
c = 13.8045 (6) Å	θ = 2.6–30.8°
α = 103.692 (4)°	µ = 0.35 mm−1
β = 99.963 (4)°	T = 100 K
γ = 101.609 (3)°	Irregular tablet, pale yellow
V = 1250.24 (9) Å3	0.4 × 0.3 × 0.1 mm
Z = 1

Oxford Diffraction Xcalibur Eos diffractometer	6443 independent reflections
Radiation source: Enhance (Mo) X-ray Source	4941 reflections with I > 2σ(I)
graphite	Rint = 0.031
Detector resolution: 16.1419 pixels mm-1	θmax = 28.7°, θmin = 2.7°
ω–scan	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −16→16
Tmin = 0.970, Tmax = 1.000	l = −18→18
26853 measured reflections

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ2(Fo2) + (0.0363P)2] where P = (Fo2 + 2Fc2)/3
6443 reflections	(Δ/σ)max = 0.001
326 parameters	Δρmax = 0.30 e Å−3
18 restraints	Δρmin = −0.28 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)5.7234 (0.0013) x - 5.6563 (0.0020) y + 7.4193 (0.0030) z = 5.4532 (0.0027)* 0.0098 (0.0008) C1 * 0.0042 (0.0011) C11 * 0.0033 (0.0011) C12 * -0.0107 (0.0010) C13 * 0.0215 (0.0007) C14 * 0.0075 (0.0008) C18 * 0.0664 (0.0009) N1 * -0.0508 (0.0008) O1 * 0.0150 (0.0006) S1 * -0.0662 (0.0006) S2 -0.8620 (0.0010) CaRms deviation of fitted atoms = 0.03517.5293 (0.0008) x - 5.2398 (0.0041) y + 0.8431 (0.0033) z = 1.0859 (0.0024)Angle to previous plane (with approximate esd) = 29.03 ( 0.02 )* -0.0015 (0.0010) C1 * 0.0157 (0.0010) C2 * 0.0006 (0.0010) C3 * -0.0152 (0.0011) C4 * 0.0063 (0.0011) C5 * 0.0109 (0.0011) C6 * -0.0015 (0.0011) C7 * -0.0092 (0.0010) C8 * -0.0036 (0.0011) C9 * -0.0025 (0.0011) C10Rms deviation of fitted atoms = 0.0086

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	Occ. (<1)
Ca	0.0000	0.5000	1.0000	0.01453 (8)
S1	0.64002 (4)	0.90145 (3)	0.93054 (2)	0.01677 (8)
S2	0.63380 (4)	0.69288 (3)	0.76538 (2)	0.01590 (8)
O1	0.25364 (11)	0.53927 (7)	0.94360 (7)	0.0198 (2)
O3	1.01513 (11)	0.87570 (7)	0.93853 (7)	0.0201 (2)
N1	0.39935 (14)	0.49923 (9)	0.81647 (8)	0.0156 (2)
H01	0.471 (2)	0.5286 (13)	0.7844 (11)	0.032 (4)*
N2	0.36142 (15)	0.81149 (9)	1.07579 (8)	0.0225 (2)
C1	0.32121 (15)	0.37980 (10)	0.77809 (9)	0.0152 (3)
C2	0.27106 (16)	0.31450 (10)	0.84051 (10)	0.0173 (3)
H2	0.2901	0.3491	0.9120	0.021*
C3	0.19158 (17)	0.19658 (11)	0.79947 (10)	0.0211 (3)
H3	0.1560	0.1523	0.8433	0.025*
C4	0.16515 (17)	0.14516 (11)	0.69724 (10)	0.0210 (3)
H4	0.1102	0.0656	0.6706	0.025*
C5	0.19573 (17)	0.15718 (11)	0.52430 (10)	0.0236 (3)
H5	0.1437	0.0773	0.4969	0.028*
C6	0.24685 (18)	0.21949 (12)	0.46050 (10)	0.0256 (3)
H6	0.2309	0.1830	0.3897	0.031*
C7	0.32322 (17)	0.33790 (12)	0.49968 (10)	0.0240 (3)
H7	0.3580	0.3813	0.4550	0.029*
C8	0.34779 (17)	0.39113 (11)	0.60195 (9)	0.0193 (3)
H8	0.3994	0.4712	0.6272	0.023*
C9	0.21843 (16)	0.20880 (10)	0.63064 (10)	0.0178 (3)
C10	0.29770 (15)	0.32891 (10)	0.67054 (9)	0.0153 (3)
C11	0.36103 (16)	0.57231 (10)	0.89338 (9)	0.0143 (2)
C12	0.44847 (15)	0.69477 (10)	0.91915 (9)	0.0139 (2)
C13	0.56499 (15)	0.75240 (10)	0.87132 (9)	0.0137 (2)
C14	0.78632 (16)	0.94911 (10)	0.85488 (9)	0.0147 (2)
H14A	0.7223	0.9213	0.7818	0.018*
H14B	0.8187	1.0338	0.8744	0.018*
C15	0.95496 (16)	0.90825 (10)	0.86744 (9)	0.0152 (3)
O2	1.03244 (11)	0.91600 (8)	0.78997 (7)	0.0246 (2)
C16	1.1903 (3)	0.8657 (3)	0.7942 (2)	0.0354 (7)	0.738 (4)
H16A	1.2878	0.9141	0.8533	0.042*	0.738 (4)
H16B	1.1571	0.7883	0.8036	0.042*	0.738 (4)
C17	1.2505 (3)	0.8589 (2)	0.69962 (17)	0.0436 (8)	0.738 (4)
H17A	1.3527	0.8250	0.7021	0.065*	0.738 (4)
H17B	1.2859	0.9359	0.6916	0.065*	0.738 (4)
H17C	1.1533	0.8113	0.6414	0.065*	0.738 (4)
C16'	1.2112 (11)	0.9059 (6)	0.7918 (7)	0.029 (2)*	0.262 (4)
H16C	1.2780	0.9128	0.8616	0.034*	0.262 (4)
H16D	1.2780	0.9625	0.7633	0.034*	0.262 (4)
C17'	1.1676 (9)	0.7828 (6)	0.7206 (5)	0.044 (2)*	0.262 (4)
H17D	1.2788	0.7609	0.7139	0.066*	0.262 (4)
H17E	1.0996	0.7794	0.6529	0.066*	0.262 (4)
H17F	1.0967	0.7301	0.7499	0.066*	0.262 (4)
C18	0.40096 (16)	0.75993 (10)	1.00605 (9)	0.0152 (2)
C91	−0.0616 (2)	0.49289 (14)	0.64737 (12)	0.0380 (4)
H91A	0.0392	0.4925	0.7000	0.057*
H91B	−0.1516	0.5204	0.6803	0.057*
H91C	−0.0198	0.5436	0.6071	0.057*
C92	−0.1421 (2)	0.37394 (14)	0.57815 (11)	0.0314 (3)
H92A	−0.2440	0.3737	0.5247	0.038*
H92B	−0.0523	0.3460	0.5439	0.038*
O93	−0.20128 (13)	0.30117 (9)	0.63788 (7)	0.0283 (2)
C94	−0.2807 (2)	0.18547 (13)	0.57820 (11)	0.0332 (4)
H94A	−0.1931	0.1539	0.5444	0.040*
H94B	−0.3842	0.1823	0.5244	0.040*
C95	−0.3405 (2)	0.11591 (14)	0.64723 (12)	0.0375 (4)
H95A	−0.4274	0.1474	0.6803	0.056*
H95B	−0.2373	0.1185	0.6997	0.056*
H95C	−0.3959	0.0364	0.6067	0.056*
O1W	−0.17859 (14)	0.37346 (9)	0.84531 (8)	0.0318 (3)
H1W	−0.173 (2)	0.3536 (15)	0.7848 (10)	0.051 (6)*
H2W	−0.252 (2)	0.3209 (14)	0.8526 (14)	0.064 (7)*
O2W	−0.07611 (14)	0.64913 (9)	0.94233 (8)	0.0277 (2)
H3W	−0.023 (2)	0.7169 (11)	0.9595 (12)	0.044 (5)*
H4W	−0.155 (2)	0.6389 (15)	0.8925 (11)	0.048 (6)*

	U11	U22	U33	U12	U13	U23
Ca	0.01563 (18)	0.01361 (17)	0.01734 (18)	0.00374 (13)	0.00750 (14)	0.00726 (13)
S1	0.01826 (16)	0.01288 (15)	0.01747 (16)	0.00078 (12)	0.00818 (12)	0.00085 (12)
S2	0.01890 (16)	0.01387 (15)	0.01454 (15)	0.00153 (12)	0.00815 (12)	0.00241 (11)
O1	0.0199 (5)	0.0174 (4)	0.0240 (5)	0.0023 (4)	0.0127 (4)	0.0061 (4)
O3	0.0200 (5)	0.0161 (4)	0.0215 (5)	0.0033 (4)	−0.0013 (4)	0.0058 (4)
N1	0.0165 (5)	0.0134 (5)	0.0162 (5)	0.0004 (4)	0.0076 (4)	0.0032 (4)
N2	0.0280 (6)	0.0196 (6)	0.0241 (6)	0.0076 (5)	0.0136 (5)	0.0074 (5)
C1	0.0118 (6)	0.0143 (6)	0.0184 (6)	0.0025 (5)	0.0029 (5)	0.0036 (5)
C2	0.0182 (6)	0.0168 (6)	0.0167 (6)	0.0039 (5)	0.0037 (5)	0.0050 (5)
C3	0.0216 (7)	0.0176 (6)	0.0262 (7)	0.0036 (5)	0.0064 (6)	0.0107 (5)
C4	0.0184 (7)	0.0131 (6)	0.0277 (7)	0.0004 (5)	0.0020 (5)	0.0038 (5)
C5	0.0192 (7)	0.0198 (7)	0.0242 (7)	0.0025 (5)	0.0018 (6)	−0.0037 (5)
C6	0.0244 (7)	0.0304 (8)	0.0165 (7)	0.0049 (6)	0.0045 (6)	−0.0017 (6)
C7	0.0243 (7)	0.0288 (7)	0.0189 (7)	0.0048 (6)	0.0079 (6)	0.0063 (6)
C8	0.0201 (7)	0.0181 (6)	0.0179 (6)	0.0017 (5)	0.0056 (5)	0.0032 (5)
C9	0.0133 (6)	0.0166 (6)	0.0211 (7)	0.0035 (5)	0.0022 (5)	0.0022 (5)
C10	0.0111 (6)	0.0168 (6)	0.0166 (6)	0.0032 (5)	0.0024 (5)	0.0031 (5)
C11	0.0129 (6)	0.0166 (6)	0.0142 (6)	0.0043 (5)	0.0035 (5)	0.0050 (5)
C12	0.0128 (6)	0.0154 (6)	0.0135 (6)	0.0036 (5)	0.0041 (5)	0.0030 (5)
C13	0.0121 (6)	0.0143 (6)	0.0135 (6)	0.0034 (5)	0.0013 (5)	0.0029 (5)
C14	0.0165 (6)	0.0130 (6)	0.0155 (6)	0.0029 (5)	0.0051 (5)	0.0050 (5)
C15	0.0152 (6)	0.0091 (5)	0.0174 (6)	−0.0010 (5)	0.0025 (5)	0.0008 (5)
O2	0.0161 (5)	0.0383 (6)	0.0213 (5)	0.0076 (4)	0.0079 (4)	0.0089 (4)
C16	0.0198 (12)	0.055 (2)	0.0368 (14)	0.0198 (14)	0.0121 (10)	0.0105 (15)
C17	0.0438 (15)	0.0669 (19)	0.0368 (13)	0.0383 (13)	0.0182 (11)	0.0195 (12)
C18	0.0151 (6)	0.0138 (6)	0.0184 (6)	0.0032 (5)	0.0056 (5)	0.0072 (5)
C91	0.0465 (10)	0.0441 (10)	0.0394 (9)	0.0246 (8)	0.0220 (8)	0.0223 (8)
C92	0.0300 (8)	0.0499 (10)	0.0230 (7)	0.0173 (7)	0.0103 (6)	0.0173 (7)
O93	0.0310 (6)	0.0366 (6)	0.0186 (5)	0.0095 (4)	0.0078 (4)	0.0078 (4)
C94	0.0259 (8)	0.0439 (9)	0.0240 (8)	0.0094 (7)	0.0017 (6)	0.0011 (7)
C95	0.0320 (9)	0.0389 (9)	0.0366 (9)	0.0044 (7)	0.0073 (7)	0.0056 (7)
O1W	0.0370 (6)	0.0330 (6)	0.0181 (5)	−0.0079 (5)	0.0103 (5)	0.0050 (5)
O2W	0.0291 (6)	0.0183 (5)	0.0353 (6)	0.0044 (4)	0.0007 (5)	0.0133 (5)

Ca—O1	2.2696 (9)	N1—H01	0.855 (16)
Ca—O2W	2.3265 (10)	C2—H2	0.9500
Ca—O1W	2.3434 (10)	C3—H3	0.9500
S1—C13	1.7686 (12)	C4—H4	0.9500
S1—C14	1.7891 (12)	C5—H5	0.9500
S2—C13	1.7037 (12)	C6—H6	0.9500
O1—C11	1.2494 (14)	C7—H7	0.9500
O3—C15	1.2064 (15)	C8—H8	0.9500
N1—C11	1.3448 (15)	C14—H14A	0.9900
N1—C1	1.4184 (15)	C14—H14B	0.9900
N2—C18	1.1518 (16)	C16—H16A	0.9900
C1—C2	1.3702 (17)	C16—H16B	0.9900
C1—C10	1.4325 (17)	C17—H17A	0.9800
C2—C3	1.4063 (17)	C17—H17B	0.9800
C3—C4	1.3643 (18)	C17—H17C	0.9800
C4—C9	1.4113 (18)	C16'—H16C	0.9900
C5—C6	1.3631 (19)	C16'—H16D	0.9900
C5—C9	1.4199 (18)	C17'—H17D	0.9800
C6—C7	1.4059 (19)	C17'—H17E	0.9800
C7—C8	1.3713 (17)	C17'—H17F	0.9800
C8—C10	1.4156 (17)	C91—H91A	0.9800
C9—C10	1.4284 (16)	C91—H91B	0.9800
C11—C12	1.4684 (16)	C91—H91C	0.9800
C12—C13	1.3996 (17)	C92—H92A	0.9900
C12—C18	1.4325 (17)	C92—H92B	0.9900
C14—C15	1.5105 (17)	C94—H94A	0.9900
C15—O2	1.3323 (15)	C94—H94B	0.9900
O2—C16'	1.433 (9)	C95—H95A	0.9800
O2—C16	1.497 (3)	C95—H95B	0.9800
C16—C17	1.455 (3)	C95—H95C	0.9800
C16'—C17'	1.545 (8)	O1W—H1W	0.824 (13)
C91—C92	1.499 (2)	O1W—H2W	0.820 (13)
C92—O93	1.4255 (17)	O2W—H3W	0.819 (13)
O93—C94	1.4277 (17)	O2W—H4W	0.810 (13)
C94—C95	1.503 (2)
O1i—Ca—O1	180.0	C9—C5—H5	119.2
O1—Ca—O2Wi	92.96 (4)	C5—C6—H6	120.1
O1i—Ca—O2W	92.96 (4)	C7—C6—H6	120.1
O1—Ca—O2W	87.04 (4)	C8—C7—H7	119.8
O2Wi—Ca—O2W	180.0	C6—C7—H7	119.8
O1—Ca—O1Wi	83.15 (3)	C7—C8—H8	119.4
O2W—Ca—O1Wi	91.93 (4)	C10—C8—H8	119.4
O1i—Ca—O1W	83.15 (4)	C15—C14—H14A	109.0
O1—Ca—O1W	96.85 (3)	S1—C14—H14A	109.0
O2Wi—Ca—O1W	91.93 (4)	C15—C14—H14B	109.0
O2W—Ca—O1W	88.07 (4)	S1—C14—H14B	109.0
O1Wi—Ca—O1W	180.0	H14A—C14—H14B	107.8
C13—S1—C14	103.00 (6)	C17—C16—H16A	109.8
C11—O1—Ca	161.36 (9)	O2—C16—H16A	109.8
C11—N1—C1	126.41 (11)	C17—C16—H16B	109.8
C2—C1—N1	122.01 (11)	O2—C16—H16B	109.8
C2—C1—C10	120.73 (11)	H16A—C16—H16B	108.2
N1—C1—C10	117.26 (11)	C16—C17—H17A	109.5
C1—C2—C3	120.42 (12)	C16—C17—H17B	109.5
C4—C3—C2	120.61 (12)	H17A—C17—H17B	109.5
C3—C4—C9	120.80 (12)	C16—C17—H17C	109.5
C6—C5—C9	121.59 (12)	H17A—C17—H17C	109.5
C5—C6—C7	119.90 (12)	H17B—C17—H17C	109.5
C8—C7—C6	120.40 (13)	O2—C16'—H16C	112.1
C7—C8—C10	121.21 (12)	C17'—C16'—H16C	112.1
C4—C9—C5	122.03 (12)	O2—C16'—H16D	112.1
C4—C9—C10	119.51 (11)	C17'—C16'—H16D	112.1
C5—C9—C10	118.46 (12)	H16C—C16'—H16D	109.7
C8—C10—C9	118.44 (11)	C16'—C17'—H17D	109.5
C8—C10—C1	123.63 (11)	C16'—C17'—H17E	109.5
C9—C10—C1	117.93 (11)	H17D—C17'—H17E	109.5
O1—C11—N1	122.08 (11)	C16'—C17'—H17F	109.5
O1—C11—C12	119.03 (11)	H17D—C17'—H17F	109.5
N1—C11—C12	118.89 (11)	H17E—C17'—H17F	109.5
C13—C12—C18	118.58 (11)	C92—C91—H91A	109.5
C13—C12—C11	129.48 (11)	C92—C91—H91B	109.5
C18—C12—C11	111.94 (10)	H91A—C91—H91B	109.5
C12—C13—S2	126.43 (9)	C92—C91—H91C	109.5
C12—C13—S1	113.61 (9)	H91A—C91—H91C	109.5
S2—C13—S1	119.95 (7)	H91B—C91—H91C	109.5
C15—C14—S1	113.08 (9)	O93—C92—H92A	109.9
O3—C15—O2	124.07 (12)	C91—C92—H92A	109.9
O3—C15—C14	125.39 (12)	O93—C92—H92B	109.9
O2—C15—C14	110.52 (10)	C91—C92—H92B	109.9
C15—O2—C16'	122.7 (4)	H92A—C92—H92B	108.3
C15—O2—C16	112.09 (14)	O93—C94—H94A	109.9
C16'—O2—C16	19.7 (3)	C95—C94—H94A	109.9
C17—C16—O2	109.5 (2)	O93—C94—H94B	109.9
O2—C16'—C17'	98.6 (5)	C95—C94—H94B	109.9
N2—C18—C12	179.36 (14)	H94A—C94—H94B	108.3
O93—C92—C91	108.82 (12)	C94—C95—H95A	109.5
C92—O93—C94	112.91 (11)	C94—C95—H95B	109.5
O93—C94—C95	109.05 (12)	H95A—C95—H95B	109.5
C11—N1—H01	116.6 (10)	C94—C95—H95C	109.5
C1—N1—H01	116.8 (10)	H95A—C95—H95C	109.5
C1—C2—H2	119.8	H95B—C95—H95C	109.5
C3—C2—H2	119.8	Ca—O1W—H1W	138.0 (12)
C4—C3—H3	119.7	Ca—O1W—H2W	113.9 (13)
C2—C3—H3	119.7	H1W—O1W—H2W	105.2 (16)
C3—C4—H4	119.6	Ca—O2W—H3W	129.2 (12)
C9—C4—H4	119.6	Ca—O2W—H4W	122.9 (13)
C6—C5—H5	119.2	H3W—O2W—H4W	107.1 (16)
O1i—Ca—O1—C11	71 (6)	Ca—O1—C11—C12	79.9 (3)
O2Wi—Ca—O1—C11	153.0 (3)	C1—N1—C11—O1	3.5 (2)
O2W—Ca—O1—C11	−27.0 (3)	C1—N1—C11—C12	−176.62 (11)
O1Wi—Ca—O1—C11	−119.3 (3)	O1—C11—C12—C13	−176.38 (12)
O1W—Ca—O1—C11	60.7 (3)	N1—C11—C12—C13	3.71 (19)
C11—N1—C1—C2	−34.63 (18)	O1—C11—C12—C18	3.10 (16)
C11—N1—C1—C10	145.94 (12)	N1—C11—C12—C18	−176.80 (11)
N1—C1—C2—C3	179.07 (11)	C18—C12—C13—S2	−177.98 (9)
C10—C1—C2—C3	−1.52 (19)	C11—C12—C13—S2	1.48 (19)
C1—C2—C3—C4	0.79 (19)	C18—C12—C13—S1	1.28 (15)
C2—C3—C4—C9	0.62 (19)	C11—C12—C13—S1	−179.27 (10)
C9—C5—C6—C7	−0.3 (2)	C14—S1—C13—C12	178.99 (9)
C5—C6—C7—C8	0.4 (2)	C14—S1—C13—S2	−1.70 (9)
C6—C7—C8—C10	0.1 (2)	C13—S1—C14—C15	−68.69 (9)
C3—C4—C9—C5	178.77 (13)	S1—C14—C15—O3	−20.07 (15)
C3—C4—C9—C10	−1.27 (19)	S1—C14—C15—O2	161.69 (8)
C6—C5—C9—C4	179.68 (13)	O3—C15—O2—C16'	−11.5 (4)
C6—C5—C9—C10	−0.29 (19)	C14—C15—O2—C16'	166.8 (3)
C7—C8—C10—C9	−0.74 (19)	O3—C15—O2—C16	7.3 (2)
C7—C8—C10—C1	179.59 (12)	C14—C15—O2—C16	−174.45 (16)
C4—C9—C10—C8	−179.15 (12)	C15—O2—C16—C17	170.4 (2)
C5—C9—C10—C8	0.82 (17)	C16'—O2—C16—C17	−63.0 (12)
C4—C9—C10—C1	0.53 (17)	C15—O2—C16'—C17'	103.4 (5)
C5—C9—C10—C1	−179.50 (12)	C16—O2—C16'—C17'	41.3 (9)
C2—C1—C10—C8	−179.49 (12)	C13—C12—C18—N2	162 (14)
N1—C1—C10—C8	−0.05 (18)	C11—C12—C18—N2	−17 (14)
C2—C1—C10—C9	0.84 (17)	C91—C92—O93—C94	179.86 (11)
N1—C1—C10—C9	−179.72 (10)	C92—O93—C94—C95	−179.38 (12)
Ca—O1—C11—N1	−100.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H01···S2	0.855 (16)	2.279 (16)	3.0274 (11)	146.2 (14)
O1W—H1W···O93	0.82 (1)	1.94 (1)	2.7531 (14)	171 (2)
O1W—H2W···N2i	0.82 (1)	2.22 (1)	2.9902 (15)	157 (2)
O2W—H3W···O3ii	0.82 (1)	2.03 (1)	2.7797 (13)	151 (2)
O2W—H4W···S2ii	0.81 (1)	2.51 (1)	3.2666 (11)	157 (2)

Table 1

Selected bond lengths (Å)

Ca—O1	2.2696 (9)
Ca—O2W	2.3265 (10)
Ca—O1W	2.3434 (10)
S1—C13	1.7686 (12)
S1—C14	1.7891 (12)
S2—C13	1.7037 (12)
O1—C11	1.2494 (14)
N1—C11	1.3448 (15)
N1—C1	1.4184 (15)
N2—C18	1.1518 (16)
C11—C12	1.4684 (16)
C12—C13	1.3996 (17)
C12—C18	1.4325 (17)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H01⋯S2	0.855 (16)	2.279 (16)	3.0274 (11)	146.2 (14)
O1W—H1W⋯O93	0.82 (1)	1.94 (1)	2.7531 (14)	171 (2)
O1W—H2W⋯N2i	0.82 (1)	2.22 (1)	2.9902 (15)	157 (2)
O2W—H3W⋯O3ii	0.82 (1)	2.03 (1)	2.7797 (13)	151 (2)
O2W—H4W⋯S2ii	0.81 (1)	2.51 (1)	3.2666 (11)	157 (2)

Symmetry codes: (i) ; (ii) .