Diaqua­bis[4-methyl-2-(4-methyl­phenyl­sulfonamido)penta­noato-κO]calcium(II)

In the title compound, [Ca(C₁₃H₁₈NO₄S)₂(H₂O)₂], a distorted CaO₄ tetra­hedron arises from the coordination of the two ligands and two water mol­ecules. A network of hydrogen bonds helps to establish the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.051
• wR factor = 0.112
• Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.83 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.61 Ratio
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         C4

Alert level C
CRYSC01_ALERT_1_C The word below has not been recognised as a standard
            identifier.
            block
CRYSC01_ALERT_1_C No recognised colour has been given for crystal colour.
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Ca1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C17
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          7

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.01
           From the CIF: _reflns_number_total               5549
           Count of symmetry unique reflns         3258
           Completeness (_total/calc)            170.32%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2291
           Fraction of Friedel pairs measured     0.703
           Are heavy atom types Z>Si present        yes
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15    = .          S
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         90

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

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

---

S1. Comment

As part of our ongoing studies of metal coordination complexes with multidentate ligands (Tai et al., 2005), the synthesis and structure of the title compound, (I), is reported.

Two O-monodentate ligands and two water molecules are attached to the calcium atom, resulting in a distorted CaO₄ tetrahedron (Fig. 1). The identical S2=O8 [1.437 (3) Å], S2=O7 [1.430 (3) Å], C14=O6 [1.243 (5) Å] and S1=O3 [1.427 (3) Å], S1=O4 [1.423 (3) Å], C1=O2 [1.254 (5) Å] bonds lengths imply double bond character. The dihedral angle between the two benzene ring mean planes (C7—C12 and C20—C25) is 129.9 (3) °.

Two molecules of water complete the structure of (I) and a network of hydrogen bonds helps to establish the crystal packing.

Related literature

For related literature, see: Tai et al. (2005).

S2. Experimental

1 mmol of calcium perchlorate was added to a solution of 4-toluenesulfonyl chloride-L-leucine (2 mmol) in 10 ml of CH₃OH/H₂O (v/v 1:1). The mixture was continuously stirred for 4 h at refluxing temperature, evaporating some methanol, then, upon cooling, the solid product was collected by filtration and dried in vacuo (yield 69%). Clear blocks of (I) were obtained by evaporation from a methanol solution after a week.

S3. Refinement

The water H atoms were located in a difference map and refined as riding in their as-found relative positions with U_iso(H) = 1.2U_eq(O). Other H atoms were placed geometrically (C—H = 0.93–0.97 Å, O—H = 0.82 Å, N—H = 0.86 Å) and refined as riding with U_iso(H) = 1.2U_eq(C,N) or 1.5U_eq(O).

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures

Fig. 1. The complex molecule in (I) with 50% probabiility ellipsoids (arbitrary spheres for the H atoms).

Diaquabis[4-methyl-2-(4-methylphenylsulfonamido)pentanoato-κO]calcium(II)

Crystal data

[Ca(C13H18NO4S)2(H2O)2]	Dx = 1.356 Mg m^−3
Mr = 644.80	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 4003 reflections
a = 5.1575 (11) Å	θ = 2.3–23.3°
b = 17.430 (2) Å	µ = 0.39 mm^−1
c = 35.147 (4) Å	T = 298 K
V = 3159.5 (8) Å^3	Colourless, block
Z = 4	0.58 × 0.40 × 0.38 mm
F(000) = 1368

Data collection

Bruker CCD area-detector diffractometer	5549 independent reflections
Radiation source: fine-focus sealed tube	4532 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
φ and ω scans	θmax = 25.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −6→6
Tmin = 0.808, Tmax = 0.868	k = −20→14
14074 measured reflections	l = −39→41

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.112	w = 1/[σ^2(Fo^2) + (0.0424P)^2 + 1.9751P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
5549 reflections	Δρmax = 0.26 e Å^−3
370 parameters	Δρmin = −0.28 e Å^−3
90 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (5)

Special details

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
Ca1	0.85026 (15)	0.64157 (4)	0.06135 (2)	0.02487 (19)
N1	1.6802 (6)	0.46340 (18)	0.13168 (10)	0.0321 (8)
H1	1.7678	0.4925	0.1149	0.039*
N2	0.0086 (6)	0.84341 (17)	0.11043 (9)	0.0298 (8)
H2	−0.0864	0.8062	0.0994	0.036*
O1	1.0994 (5)	0.56081 (16)	0.09914 (8)	0.0379 (8)
O2	1.5023 (6)	0.56391 (15)	0.07629 (8)	0.0369 (7)
O3	1.9911 (6)	0.36387 (18)	0.11820 (10)	0.0559 (9)
O4	1.5574 (6)	0.32834 (17)	0.14181 (10)	0.0549 (10)
O5	0.5959 (5)	0.73580 (15)	0.09304 (8)	0.0341 (7)
O6	0.2036 (5)	0.72545 (15)	0.06731 (8)	0.0369 (7)
O7	0.1982 (6)	0.91204 (16)	0.05345 (7)	0.0386 (7)
O8	−0.2625 (5)	0.92264 (17)	0.06999 (8)	0.0451 (8)
O9	0.6424 (8)	0.69671 (18)	0.00867 (8)	0.0613 (10)
H9A	0.4981	0.7103	0.0182	0.074*
H9B	0.6140	0.6662	−0.0097	0.074*
O10	1.0908 (6)	0.57833 (18)	0.01260 (9)	0.0545 (9)
H10A	1.0654	0.5833	−0.0112	0.065*
H10B	1.2449	0.5779	0.0211	0.065*
S1	1.7171 (2)	0.37528 (6)	0.11838 (4)	0.0408 (3)
S2	0.0025 (2)	0.91630 (6)	0.08220 (3)	0.0324 (3)
C1	1.3381 (8)	0.5440 (2)	0.10069 (11)	0.0292 (9)
C2	1.4202 (8)	0.4970 (2)	0.13530 (11)	0.0312 (10)
H2A	1.2950	0.4553	0.1389	0.037*
C3	1.4144 (10)	0.5481 (3)	0.17045 (13)	0.0488 (13)
H3A	1.5502	0.5863	0.1681	0.059*
H3B	1.2499	0.5751	0.1710	0.059*
C4	1.4492 (10)	0.5064 (3)	0.20805 (13)	0.0532 (13)
H4	1.6039	0.4740	0.2058	0.064*
C5	1.2227 (13)	0.4545 (5)	0.21638 (18)	0.106 (2)
H5A	1.0701	0.4849	0.2205	0.159*
H5B	1.2586	0.4248	0.2388	0.159*
H5C	1.1949	0.4207	0.1952	0.159*
C6	1.4963 (17)	0.5625 (4)	0.24014 (17)	0.100 (2)
H6A	1.3482	0.5954	0.2429	0.150*
H6B	1.6467	0.5929	0.2345	0.150*
H6C	1.5237	0.5348	0.2634	0.150*
C7	1.6044 (9)	0.3669 (2)	0.07123 (13)	0.0397 (11)
C8	1.3987 (9)	0.3197 (2)	0.06278 (15)	0.0471 (12)
H8	1.3225	0.2899	0.0817	0.057*
C9	1.3070 (11)	0.3169 (3)	0.02595 (15)	0.0544 (14)
H9	1.1670	0.2852	0.0205	0.065*
C10	1.4153 (9)	0.3596 (3)	−0.00300 (14)	0.0487 (12)
C11	1.6259 (11)	0.4066 (3)	0.00626 (15)	0.0527 (13)
H11	1.7040	0.4360	−0.0126	0.063*
C12	1.7187 (9)	0.4097 (2)	0.04283 (14)	0.0459 (12)
H12	1.8597	0.4409	0.0485	0.055*
C13	1.3128 (12)	0.3565 (3)	−0.04291 (15)	0.0747 (17)
H13A	1.1532	0.3282	−0.0433	0.112*
H13B	1.4372	0.3316	−0.0591	0.112*
H13C	1.2823	0.4077	−0.0519	0.112*
C14	0.3589 (8)	0.7525 (2)	0.09079 (11)	0.0287 (9)
C15	0.2574 (8)	0.8097 (2)	0.12076 (11)	0.0311 (10)
H15	0.3851	0.8507	0.1241	0.037*
C16	0.2253 (10)	0.7668 (3)	0.15842 (13)	0.0485 (12)
H16A	0.0999	0.7259	0.1547	0.058*
H16B	0.3896	0.7430	0.1648	0.058*
C17	0.1382 (12)	0.8154 (3)	0.19202 (13)	0.0525 (12)
H17	−0.0259	0.8400	0.1850	0.063*
C18	0.3295 (13)	0.8783 (4)	0.20161 (17)	0.090 (2)
H18A	0.3598	0.9093	0.1795	0.135*
H18B	0.4898	0.8558	0.2098	0.135*
H18C	0.2601	0.9097	0.2216	0.135*
C19	0.0868 (19)	0.7650 (4)	0.22628 (16)	0.110 (3)
H19A	0.2438	0.7392	0.2335	0.166*
H19B	−0.0435	0.7277	0.2200	0.166*
H19C	0.0275	0.7961	0.2471	0.166*
C20	0.0724 (8)	0.9945 (2)	0.11172 (12)	0.0324 (10)
C21	0.2778 (9)	1.0421 (2)	0.10399 (13)	0.0413 (11)
H21	0.3907	1.0310	0.0841	0.050*
C22	0.3151 (11)	1.1071 (2)	0.12623 (13)	0.0494 (13)
H22	0.4537	1.1395	0.1210	0.059*
C23	0.1494 (11)	1.1245 (2)	0.15617 (13)	0.0506 (13)
C24	−0.0499 (11)	1.0745 (3)	0.16340 (14)	0.0567 (15)
H24	−0.1618	1.0846	0.1835	0.068*
C25	−0.0886 (10)	1.0103 (3)	0.14186 (13)	0.0492 (13)
H25	−0.2244	0.9772	0.1476	0.059*
C26	0.1876 (14)	1.1967 (3)	0.17961 (16)	0.081 (2)
H26A	0.1332	1.2405	0.1651	0.121*
H26B	0.3675	1.2019	0.1861	0.121*
H26C	0.0862	1.1933	0.2025	0.121*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ca1	0.0183 (4)	0.0281 (4)	0.0282 (4)	−0.0003 (4)	−0.0001 (4)	0.0012 (3)
N1	0.0190 (19)	0.0360 (18)	0.041 (2)	0.0032 (16)	−0.0011 (17)	0.0109 (15)
N2	0.0227 (18)	0.0241 (17)	0.043 (2)	0.0018 (15)	−0.0004 (18)	−0.0088 (14)
O1	0.0176 (16)	0.0478 (18)	0.0483 (19)	0.0029 (14)	−0.0024 (13)	0.0210 (14)
O2	0.0287 (16)	0.0385 (17)	0.0434 (17)	−0.0011 (14)	0.0052 (15)	0.0130 (13)
O3	0.0298 (17)	0.0490 (19)	0.089 (3)	0.0144 (17)	−0.0061 (19)	0.0041 (19)
O4	0.049 (2)	0.0426 (18)	0.073 (2)	−0.0043 (16)	−0.0045 (19)	0.0275 (17)
O5	0.0152 (16)	0.0380 (16)	0.0493 (18)	0.0023 (13)	−0.0013 (13)	−0.0079 (13)
O6	0.0211 (16)	0.0387 (16)	0.0509 (19)	0.0002 (13)	−0.0084 (14)	−0.0155 (14)
O7	0.0358 (18)	0.0503 (17)	0.0296 (15)	−0.0021 (15)	0.0089 (14)	−0.0053 (13)
O8	0.0283 (17)	0.0517 (18)	0.055 (2)	0.0098 (15)	−0.0129 (15)	−0.0051 (16)
O9	0.076 (3)	0.075 (2)	0.0337 (18)	0.022 (2)	−0.0120 (19)	0.0049 (16)
O10	0.044 (2)	0.077 (2)	0.0420 (18)	0.0081 (19)	0.0030 (16)	−0.0154 (17)
S1	0.0280 (6)	0.0339 (6)	0.0606 (8)	0.0043 (5)	−0.0029 (6)	0.0105 (5)
S2	0.0246 (5)	0.0365 (6)	0.0362 (6)	0.0038 (5)	−0.0019 (5)	−0.0051 (5)
C1	0.023 (2)	0.027 (2)	0.037 (2)	−0.003 (2)	−0.003 (2)	0.0047 (17)
C2	0.022 (2)	0.037 (2)	0.035 (2)	0.0023 (19)	0.0007 (19)	0.0125 (19)
C3	0.045 (3)	0.054 (3)	0.048 (3)	0.017 (2)	−0.002 (2)	0.006 (2)
C4	0.045 (3)	0.073 (3)	0.041 (3)	0.013 (3)	−0.004 (2)	0.008 (2)
C5	0.077 (5)	0.171 (6)	0.070 (4)	−0.023 (5)	−0.002 (4)	0.050 (4)
C6	0.130 (6)	0.111 (5)	0.059 (4)	0.029 (5)	−0.010 (4)	−0.013 (4)
C7	0.033 (2)	0.030 (2)	0.056 (3)	0.004 (2)	0.005 (2)	0.003 (2)
C8	0.044 (3)	0.040 (3)	0.058 (3)	0.001 (2)	0.010 (3)	0.002 (2)
C9	0.047 (4)	0.044 (3)	0.073 (4)	−0.008 (3)	0.000 (3)	−0.007 (3)
C10	0.045 (3)	0.044 (3)	0.058 (3)	0.003 (3)	−0.007 (3)	−0.002 (3)
C11	0.052 (3)	0.045 (3)	0.061 (3)	−0.003 (3)	0.008 (3)	0.009 (2)
C12	0.037 (3)	0.036 (2)	0.065 (3)	−0.007 (2)	−0.002 (3)	0.006 (2)
C13	0.079 (5)	0.075 (4)	0.069 (4)	−0.007 (4)	−0.010 (3)	−0.004 (3)
C14	0.021 (2)	0.026 (2)	0.039 (2)	−0.0007 (19)	0.002 (2)	0.0000 (18)
C15	0.030 (2)	0.029 (2)	0.034 (2)	0.0027 (18)	−0.002 (2)	−0.0069 (18)
C16	0.051 (3)	0.047 (3)	0.047 (3)	0.012 (2)	0.006 (2)	0.004 (2)
C17	0.058 (3)	0.058 (3)	0.041 (3)	0.010 (3)	0.011 (3)	0.002 (2)
C18	0.096 (5)	0.104 (4)	0.070 (4)	0.007 (4)	−0.001 (4)	−0.037 (3)
C19	0.170 (7)	0.101 (5)	0.060 (4)	0.024 (5)	0.042 (4)	0.023 (3)
C20	0.026 (2)	0.032 (2)	0.039 (2)	0.0051 (19)	−0.002 (2)	0.0017 (19)
C21	0.039 (3)	0.040 (2)	0.044 (3)	−0.004 (2)	0.007 (2)	−0.001 (2)
C22	0.057 (3)	0.041 (3)	0.050 (3)	−0.015 (3)	−0.001 (3)	0.001 (2)
C23	0.066 (4)	0.034 (2)	0.052 (3)	−0.008 (3)	0.005 (3)	−0.002 (2)
C24	0.069 (4)	0.052 (3)	0.049 (3)	−0.010 (3)	0.022 (3)	−0.013 (3)
C25	0.051 (3)	0.043 (3)	0.054 (3)	−0.010 (2)	0.023 (3)	−0.005 (2)
C26	0.125 (6)	0.045 (3)	0.072 (4)	−0.007 (4)	0.012 (4)	−0.016 (3)

Geometric parameters (Å, º)

Ca1—O2^i	2.308 (3)	C6—H6C	0.9600
Ca1—O1	2.323 (3)	C7—C8	1.375 (6)
Ca1—O9	2.345 (3)	C7—C12	1.378 (6)
Ca1—O6^ii	2.346 (3)	C8—C9	1.379 (7)
Ca1—O5	2.379 (3)	C8—H8	0.9300
Ca1—O10	2.385 (3)	C9—C10	1.378 (7)
Ca1—H9A	2.6516	C9—H9	0.9300
Ca1—H10B	2.7147	C10—C11	1.399 (7)
N1—C2	1.469 (5)	C10—C13	1.500 (7)
N1—S1	1.617 (3)	C11—C12	1.372 (7)
N1—H1	0.9000	C11—H11	0.9300
N2—C15	1.458 (5)	C12—H12	0.9300
N2—S2	1.612 (3)	C13—H13A	0.9600
N2—H2	0.9000	C13—H13B	0.9600
O1—C1	1.267 (5)	C13—H13C	0.9600
O2—C1	1.254 (5)	C14—C15	1.542 (5)
O2—Ca1^ii	2.308 (3)	C15—C16	1.529 (6)
O3—S1	1.427 (3)	C15—H15	0.9800
O4—S1	1.423 (3)	C16—C17	1.521 (6)
O5—C14	1.259 (5)	C16—H16A	0.9700
O6—C14	1.243 (5)	C16—H16B	0.9700
O6—Ca1^i	2.346 (3)	C17—C18	1.513 (8)
O7—S2	1.430 (3)	C17—C19	1.514 (7)
O8—S2	1.437 (3)	C17—H17	0.9800
O9—H9A	0.8500	C18—H18A	0.9600
O9—H9B	0.8499	C18—H18B	0.9600
O10—H10A	0.8498	C18—H18C	0.9600
O10—H10B	0.8498	C19—H19A	0.9600
S1—C7	1.762 (5)	C19—H19B	0.9600
S2—C20	1.750 (4)	C19—H19C	0.9600
C1—C2	1.526 (5)	C20—C21	1.373 (6)
C2—C3	1.523 (6)	C20—C25	1.374 (6)
C2—H2A	0.9800	C21—C22	1.389 (6)
C3—C4	1.519 (6)	C21—H21	0.9300
C3—H3A	0.9700	C22—C23	1.389 (7)
C3—H3B	0.9700	C22—H22	0.9300
C4—C5	1.506 (8)	C23—C24	1.371 (7)
C4—C6	1.512 (8)	C23—C26	1.516 (6)
C4—H4	0.9800	C24—C25	1.366 (6)
C5—H5A	0.9600	C24—H24	0.9300
C5—H5B	0.9600	C25—H25	0.9300
C5—H5C	0.9600	C26—H26A	0.9600
C6—H6A	0.9600	C26—H26B	0.9600
C6—H6B	0.9600	C26—H26C	0.9600
O2^i—Ca1—O1	86.82 (10)	H6A—C6—H6B	109.5
O2^i—Ca1—O9	93.70 (12)	C4—C6—H6C	109.5
O1—Ca1—O9	162.26 (12)	H6A—C6—H6C	109.5
O2^i—Ca1—O6^ii	161.64 (11)	H6B—C6—H6C	109.5
O1—Ca1—O6^ii	84.08 (10)	C8—C7—C12	119.8 (4)
O9—Ca1—O6^ii	99.80 (12)	C8—C7—S1	120.5 (4)
O2^i—Ca1—O5	82.51 (10)	C12—C7—S1	119.7 (4)
O1—Ca1—O5	117.11 (11)	C7—C8—C9	119.2 (5)
O9—Ca1—O5	80.48 (11)	C7—C8—H8	120.4
O6^ii—Ca1—O5	87.49 (9)	C9—C8—H8	120.4
O2^i—Ca1—O10	107.26 (11)	C10—C9—C8	122.4 (5)
O1—Ca1—O10	80.97 (11)	C10—C9—H9	118.8
O9—Ca1—O10	81.95 (12)	C8—C9—H9	118.8
O6^ii—Ca1—O10	87.03 (11)	C9—C10—C11	117.3 (5)
O5—Ca1—O10	160.42 (11)	C9—C10—C13	121.9 (5)
O2^i—Ca1—H9A	82.1	C11—C10—C13	120.8 (5)
O1—Ca1—H9A	168.4	C12—C11—C10	120.8 (5)
O9—Ca1—H9A	18.3	C12—C11—H11	119.6
O6^ii—Ca1—H9A	107.6	C10—C11—H11	119.6
O5—Ca1—H9A	65.0	C11—C12—C7	120.5 (4)
O10—Ca1—H9A	98.9	C11—C12—H12	119.7
O2^i—Ca1—H10B	117.5	C7—C12—H12	119.7
O1—Ca1—H10B	68.6	C10—C13—H13A	109.5
O9—Ca1—H10B	95.7	C10—C13—H13B	109.5
O6^ii—Ca1—H10B	73.7	H13A—C13—H13B	109.5
O5—Ca1—H10B	159.9	C10—C13—H13C	109.5
O10—Ca1—H10B	17.7	H13A—C13—H13C	109.5
H9A—Ca1—H10B	113.6	H13B—C13—H13C	109.5
C2—N1—S1	120.7 (3)	O6—C14—O5	125.4 (4)
C2—N1—H1	106.9	O6—C14—C15	118.7 (4)
S1—N1—H1	106.7	O5—C14—C15	115.8 (4)
C15—N2—S2	119.2 (3)	N2—C15—C16	108.5 (3)
C15—N2—H2	107.2	N2—C15—C14	112.9 (3)
S2—N2—H2	107.1	C16—C15—C14	108.2 (3)
C1—O1—Ca1	134.6 (3)	N2—C15—H15	109.1
C1—O2—Ca1^ii	147.5 (3)	C16—C15—H15	109.1
C14—O5—Ca1	131.7 (3)	C14—C15—H15	109.1
C14—O6—Ca1^i	142.8 (3)	C17—C16—C15	115.6 (4)
Ca1—O9—H9A	101.7	C17—C16—H16A	108.4
Ca1—O9—H9B	115.1	C15—C16—H16A	108.4
H9A—O9—H9B	108.9	C17—C16—H16B	108.4
Ca1—O10—H10A	125.3	C15—C16—H16B	108.4
Ca1—O10—H10B	103.7	H16A—C16—H16B	107.5
H10A—O10—H10B	119.5	C18—C17—C19	110.9 (5)
O4—S1—O3	119.7 (2)	C18—C17—C16	112.6 (4)
O4—S1—N1	108.1 (2)	C19—C17—C16	110.2 (4)
O3—S1—N1	104.49 (19)	C18—C17—H17	107.6
O4—S1—C7	107.8 (2)	C19—C17—H17	107.6
O3—S1—C7	108.1 (2)	C16—C17—H17	107.6
N1—S1—C7	108.15 (18)	C17—C18—H18A	109.5
O7—S2—O8	117.66 (18)	C17—C18—H18B	109.5
O7—S2—N2	112.35 (18)	H18A—C18—H18B	109.5
O8—S2—N2	105.22 (19)	C17—C18—H18C	109.5
O7—S2—C20	108.30 (19)	H18A—C18—H18C	109.5
O8—S2—C20	108.24 (19)	H18B—C18—H18C	109.5
N2—S2—C20	104.17 (18)	C17—C19—H19A	109.5
O2—C1—O1	124.2 (4)	C17—C19—H19B	109.5
O2—C1—C2	120.4 (4)	H19A—C19—H19B	109.5
O1—C1—C2	115.3 (4)	C17—C19—H19C	109.5
N1—C2—C3	108.7 (3)	H19A—C19—H19C	109.5
N1—C2—C1	113.5 (3)	H19B—C19—H19C	109.5
C3—C2—C1	109.1 (3)	C21—C20—C25	119.8 (4)
N1—C2—H2A	108.5	C21—C20—S2	120.8 (3)
C3—C2—H2A	108.5	C25—C20—S2	119.3 (3)
C1—C2—H2A	108.5	C20—C21—C22	119.2 (4)
C4—C3—C2	115.0 (4)	C20—C21—H21	120.4
C4—C3—H3A	108.5	C22—C21—H21	120.4
C2—C3—H3A	108.5	C21—C22—C23	121.3 (5)
C4—C3—H3B	108.5	C21—C22—H22	119.3
C2—C3—H3B	108.5	C23—C22—H22	119.3
H3A—C3—H3B	107.5	C24—C23—C22	117.5 (4)
C5—C4—C6	111.6 (5)	C24—C23—C26	121.6 (5)
C5—C4—C3	111.4 (4)	C22—C23—C26	120.9 (5)
C6—C4—C3	111.0 (5)	C25—C24—C23	121.8 (5)
C5—C4—H4	107.6	C25—C24—H24	119.1
C6—C4—H4	107.6	C23—C24—H24	119.1
C3—C4—H4	107.6	C24—C25—C20	120.2 (4)
C4—C5—H5A	109.5	C24—C25—H25	119.9
C4—C5—H5B	109.5	C20—C25—H25	119.9
H5A—C5—H5B	109.5	C23—C26—H26A	109.5
C4—C5—H5C	109.5	C23—C26—H26B	109.5
H5A—C5—H5C	109.5	H26A—C26—H26B	109.5
H5B—C5—H5C	109.5	C23—C26—H26C	109.5
C4—C6—H6A	109.5	H26A—C26—H26C	109.5
C4—C6—H6B	109.5	H26B—C26—H26C	109.5
O2^i—Ca1—O1—C1	155.9 (4)	C7—C8—C9—C10	0.5 (7)
O9—Ca1—O1—C1	63.7 (6)	C8—C9—C10—C11	0.2 (7)
O6^ii—Ca1—O1—C1	−40.1 (4)	C8—C9—C10—C13	−179.6 (5)
O5—Ca1—O1—C1	−124.2 (4)	C9—C10—C11—C12	−0.2 (7)
O10—Ca1—O1—C1	47.9 (4)	C13—C10—C11—C12	179.6 (5)
O2^i—Ca1—O5—C14	−45.5 (4)	C10—C11—C12—C7	−0.5 (7)
O1—Ca1—O5—C14	−128.1 (3)	C8—C7—C12—C11	1.2 (7)
O9—Ca1—O5—C14	49.5 (4)	S1—C7—C12—C11	−177.0 (4)
O6^ii—Ca1—O5—C14	149.9 (4)	Ca1^i—O6—C14—O5	108.2 (5)
O10—Ca1—O5—C14	76.0 (5)	Ca1^i—O6—C14—C15	−69.9 (5)
C2—N1—S1—O4	−51.5 (4)	Ca1—O5—C14—O6	−7.3 (6)
C2—N1—S1—O3	179.9 (3)	Ca1—O5—C14—C15	170.9 (2)
C2—N1—S1—C7	64.9 (4)	S2—N2—C15—C16	156.8 (3)
C15—N2—S2—O7	36.1 (3)	S2—N2—C15—C14	−83.2 (4)
C15—N2—S2—O8	165.3 (3)	O6—C14—C15—N2	−18.4 (5)
C15—N2—S2—C20	−80.9 (3)	O5—C14—C15—N2	163.3 (3)
Ca1^ii—O2—C1—O1	107.7 (5)	O6—C14—C15—C16	101.7 (4)
Ca1^ii—O2—C1—C2	−71.6 (6)	O5—C14—C15—C16	−76.6 (5)
Ca1—O1—C1—O2	−9.3 (7)	N2—C15—C16—C17	−60.0 (5)
Ca1—O1—C1—C2	170.0 (3)	C14—C15—C16—C17	177.2 (4)
S1—N1—C2—C3	140.5 (3)	C15—C16—C17—C18	−61.5 (6)
S1—N1—C2—C1	−97.9 (4)	C15—C16—C17—C19	174.1 (5)
O2—C1—C2—N1	−14.3 (5)	O7—S2—C20—C21	3.6 (4)
O1—C1—C2—N1	166.3 (3)	O8—S2—C20—C21	−125.0 (4)
O2—C1—C2—C3	107.1 (4)	N2—S2—C20—C21	123.4 (4)
O1—C1—C2—C3	−72.3 (5)	O7—S2—C20—C25	−179.7 (3)
N1—C2—C3—C4	−65.2 (5)	O8—S2—C20—C25	51.7 (4)
C1—C2—C3—C4	170.6 (4)	N2—S2—C20—C25	−59.9 (4)
C2—C3—C4—C5	−66.8 (6)	C25—C20—C21—C22	−1.9 (7)
C2—C3—C4—C6	168.2 (5)	S2—C20—C21—C22	174.9 (3)
O4—S1—C7—C8	−1.2 (4)	C20—C21—C22—C23	0.3 (7)
O3—S1—C7—C8	129.5 (4)	C21—C22—C23—C24	1.1 (7)
N1—S1—C7—C8	−117.9 (4)	C21—C22—C23—C26	−178.4 (5)
O4—S1—C7—C12	177.0 (3)	C22—C23—C24—C25	−0.9 (8)
O3—S1—C7—C12	−52.3 (4)	C26—C23—C24—C25	178.6 (5)
N1—S1—C7—C12	60.3 (4)	C23—C24—C25—C20	−0.7 (8)
C12—C7—C8—C9	−1.2 (7)	C21—C20—C25—C24	2.1 (7)
S1—C7—C8—C9	177.0 (4)	S2—C20—C25—C24	−174.7 (4)

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