Structure determination of seven phases and solvates of Pigment Yellow 183 and Pigment Yellow 191 from X-ray powder and single-crystal data

The crystal structures of two industrially produced laked yellow pigments, Pigment Yellow 183 [P.Y. 183, Ca(C₁₆H₁₀Cl₂N₄O₇S₂), α phase] and Pigment Yellow 191 [P.Y. 191, Ca(C₁₇H₁₃ClN₄O₇S₂), α and β phases], were determined from laboratory X-ray powder diffraction data. The coordinates of the molecular fragments of the crystal structures were found by means of real-space methods (simulated annealing) with the program DASH. The coordinates of the calcium ions and the water molecules were determined by combining real-space methods (DASH and MRIA) and repeated Rietveld refinements (TOPAS) of the partially finished crystal structures. TOPAS was also used for the final Rietveld refinements. The crystal structure of β-P.Y. 183 was determined from single-crystal data. The α phases of the two pigments are isostructural, whereas the β phases are not. All four phases exhibit a double-layer structure, built from nonpolar layers containing the C/N backbone and polar layers containing the calcium ions, sulfonate groups and water molecules. Furthermore, the crystal structures of an N,N-dimethylformamide solvate of P.Y. 183, and of P.Y. 191 solvates with N,N-dimethylformamide and N,N-dimethylacetamide were determined by single-crystal X-ray analysis.

Computing details

Data collection: STOE WINXPOW (STOE & CIE GmbH, 2004) for PY183alpha, PY191alpha, PY191beta; X-AREA (Stoe & Cie, 2001) for PY1833DMF, PY1834DMAc, PY1914DMF. Cell refinement: TOPAS (A.A.Coelho, 2006) for PY183alpha, PY191alpha, PY191beta; X-AREA (Stoe & Cie, 2001) for PY1833DMF, PY1834DMAc, PY1914DMF. Data reduction: DASH (W.I.F.David et al., 2006) for PY183alpha, PY191alpha, PY191beta; X-AREA (Stoe & Cie, 2001) for PY1833DMF, PY1834DMAc, PY1914DMF. Program(s) used to solve structure: DASH (W.I.F.David et al., 2006) for PY183alpha, PY191alpha, PY191beta; SHELXS97 (Sheldrick, 1990) for PY183beta, PY1833DMF, PY1834DMAc, PY1914DMF. Program(s) used to refine structure: TOPAS (A.A.Coelho, 2006) for PY183alpha, PY191alpha, PY191beta; SHELXL97 (Sheldrick, 1997) for PY183beta, PY1833DMF, PY1834DMAc, PY1914DMF. Molecular graphics: Mercury (Macrea et al., 2006) for PY183alpha, PY191alpha, PY191beta; XP in SHELXTL-Plus (Sheldrick, 1991) for PY1833DMF, PY1834DMAc, PY1914DMF. Software used to prepare material for publication: DASH, TOPAS, Mercury for PY183alpha, PY191alpha, PY191beta.

Figures

(PY183alpha)

Crystal data

C16H12CaCl2N4O8S2	Z = 2
Mr = 563.42	F(000) = 572
Triclinic, P1	Dx = 1.803 Mg m^−3
Hall symbol: -P 1	Cu Kα1 radiation, λ = 1.54056 Å
a = 5.6894 (3) Å	µ = 7.38 mm^−1
b = 10.5943 (6) Å	T = 293 K
c = 18.526 (1) Å	Particle morphology: no specific habit
α = 73.316 (5)°	yellow
β = 87.842 (3)°	flat_sheet, 10 × 1.2 mm
γ = 76.127 (3)°	Specimen preparation: Prepared at 293 K and 0.00 kPa
V = 1037.8 (1) Å^3

Data collection

STOE-Stadi-P diffractometer	Data collection mode: transmission
Radiation source: sealed X-ray tube, laboratory diffractometer	Scan method: step
Primary focussing, Ge 111 monochromator	2θmin = 3.00°, 2θmax = 34.00°, 2θstep = 0.02°
Specimen mounting: flat sample holder

Refinement

Refinement on Inet	181 parameters
Least-squares matrix: full with fixed elements per cycle	117 restraints
Rp = 0.061	0 constraints
Rwp = 0.071	H-atom parameters not refined
Rexp = 0.068	Weighting scheme based on measured s.u.'s w = 1/σ[Yobs]^2
χ^2 = 1.040	(Δ/σ)max = 0.001
1550 data points	Background function: Chebyshev polynomial with 10 terms
Excluded region(s): 33.3 to 34 degrees 2theta excluded as contains an incompletely measured peak which was difficult to cover in the refinement	Preferred orientation correction: none
Profile function: modified Thompson-Cox-Hastings pseudo-Voigt (Young, 1993)

Special details

Experimental. specimen was rotated in its plane

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

	x	y	z	Biso*/Beq
C1	1.0739 (12)	−0.8161 (6)	0.1361 (4)	0.3 (3)
N2	0.9341 (14)	−0.8966 (7)	0.1372 (5)	0.3 (3)
C3	1.1986 (11)	−0.8057 (6)	0.2024 (3)	0.3 (3)
C4	1.1455 (12)	−0.7165 (6)	0.0715 (4)	0.3 (3)
N5	0.8795 (14)	−0.9652 (7)	0.2043 (4)	0.3 (3)
O6	1.1932 (15)	−0.8687 (9)	0.2680 (5)	0.3 (3)
N7	1.3226 (9)	−0.7078 (5)	0.1716 (4)	0.3 (3)
N8	1.2895 (10)	−0.6537 (6)	0.0921 (4)	0.3 (3)
C9	1.0773 (12)	−0.6810 (6)	−0.0104 (4)	0.3 (3)
H10	0.921 (8)	−0.953 (4)	0.2439 (17)	0.4 (3)
C11	0.7200 (12)	−1.0484 (7)	0.2072 (4)	0.3 (3)
C12	1.4670 (11)	−0.6574 (6)	0.2087 (4)	0.3 (3)
H13	1.055 (8)	−0.583 (3)	−0.033 (2)	0.4 (3)
H14	0.922 (8)	−0.704 (4)	−0.016 (3)	0.4 (3)
H15	1.212 (7)	−0.731 (4)	−0.035 (2)	0.4 (3)
C16	0.6825 (11)	−1.1397 (7)	0.2763 (4)	0.3 (3)
C17	0.5947 (12)	−1.0404 (7)	0.1391 (4)	0.3 (3)
C18	1.4531 (12)	−0.6785 (6)	0.2858 (4)	0.3 (3)
C19	1.6200 (12)	−0.5827 (6)	0.1667 (4)	0.3 (3)
S20	0.8236 (12)	−1.1604 (6)	0.3649 (4)	0.3 (3)
C21	0.5246 (12)	−1.2219 (6)	0.2783 (4)	0.3 (3)
C22	0.4371 (11)	−1.1249 (6)	0.1436 (4)	0.3 (3)
H23	0.615 (7)	−0.978 (4)	0.0904 (18)	0.4 (3)
H24	1.349 (7)	−0.729 (4)	0.314 (2)	0.4 (3)
C25	1.5968 (12)	−0.6245 (7)	0.3215 (4)	0.3 (3)
C26	1.7608 (13)	−0.5302 (6)	0.2038 (4)	0.3 (3)
H27	1.629 (7)	−0.568 (4)	0.113 (2)	0.4 (3)
O28	0.660 (3)	−1.0673 (14)	0.3995 (8)	0.3 (3)
O29	1.042 (2)	−1.1171 (17)	0.3426 (10)	0.3 (3)
O30	0.854 (3)	−1.3035 (12)	0.4061 (11)	0.3 (3)
H31	0.501 (7)	−1.284 (4)	0.3254 (19)	0.4 (3)
C32	0.4040 (12)	−1.2140 (5)	0.2127 (4)	0.3 (3)
Cl33	0.2917 (14)	−1.1154 (8)	0.0620 (4)	0.2 (5)
S34	1.5775 (12)	−0.6519 (6)	0.4202 (4)	0.3 (3)
C35	1.7504 (13)	−0.5507 (7)	0.2816 (4)	0.3 (3)
H36	1.863 (7)	−0.481 (3)	0.175 (2)	0.4 (3)
Cl37	0.2108 (13)	−1.3162 (7)	0.2176 (5)	0.2 (5)
O38	1.612 (3)	−0.7977 (11)	0.4523 (10)	0.3 (3)
O39	1.760 (2)	−0.5973 (15)	0.4438 (10)	0.3 (3)
O40	1.331 (2)	−0.5828 (16)	0.4328 (10)	0.3 (3)
H41	1.845 (7)	−0.516 (4)	0.308 (2)	0.4 (3)
Ca1	1	−1.5	0.5	0.3 (3)
Ca2	0.5	−1	0.5	0.3 (3)
O44	0.846 (4)	−1.074 (3)	0.5722 (13)	0.3 (3)
H45	1.01098	−1.11626	0.55218	0.4 (3)
H46	0.86322	−1.0578	0.62213	0.4 (3)

Geometric parameters (Å, º)

C1—N2	1.29 (1)	C17—C22	1.39 (1)
C1—C3	1.48 (1)	C17—H23	0.97 (3)
C1—C4	1.472 (9)	C18—H24	0.94 (4)
N2—N5	1.31 (1)	C18—C25	1.39 (1)
C3—O6	1.21 (1)	C19—C26	1.38 (1)
C3—N7	1.369 (8)	C19—H27	0.96 (4)
C4—N8	1.30 (1)	S20—O28	1.46 (2)
C4—C9	1.50 (1)	S20—O29	1.43 (1)
N5—H10	0.83 (4)	S20—O30	1.46 (1)
N5—C11	1.40 (1)	C21—H31	0.96 (3)
N7—N8	1.42 (1)	C21—C32	1.39 (1)
N7—C12	1.37 (1)	C22—C32	1.395 (8)
C9—H13	0.98 (3)	C22—Cl33	1.72 (1)
C9—H14	0.99 (5)	C25—S34	1.77 (1)
C9—H15	1.00 (4)	C25—C35	1.37 (1)
C11—C16	1.412 (9)	C26—C35	1.39 (1)
C11—C17	1.44 (1)	C26—H36	0.93 (4)
C12—C18	1.38 (1)	C32—Cl37	1.70 (1)
C12—C19	1.386 (9)	S34—O38	1.45 (1)
C16—S20	1.79 (1)	S34—O40	1.46 (1)
C16—C21	1.39 (1)	C35—H41	0.93 (5)
N2—C1—C3	126.0 (6)	C12—C18—H24	121 (3)
N2—C1—C4	129.1 (7)	C12—C18—C25	118.8 (6)
C3—C1—C4	104.9 (6)	H24—C18—C25	120 (3)
C1—N2—N5	115.9 (8)	C12—C19—C26	118.3 (7)
C1—C3—O6	128.5 (7)	C12—C19—H27	121 (3)
C1—C3—N7	103.5 (5)	C26—C19—H27	121 (3)
O6—C3—N7	128.0 (8)	C16—S20—O28	105.9 (7)
C1—C4—N8	111.3 (6)	C16—S20—O29	102.7 (8)
C1—C4—C9	129.9 (7)	C16—S20—O30	105.3 (9)
N8—C4—C9	118.8 (6)	O28—S20—O30	114 (1)
N2—N5—H10	122 (3)	O29—S20—O30	116 (1)
N2—N5—C11	117.3 (8)	C16—C21—H31	119 (3)
H10—N5—C11	120 (3)	C16—C21—C32	120.0 (5)
C3—N7—N8	113.7 (6)	H31—C21—C32	121 (3)
C3—N7—C12	127.5 (6)	C17—C22—C32	119.9 (6)
N8—N7—C12	118.8 (5)	C17—C22—Cl33	117.8 (5)
C4—N8—N7	106.6 (5)	C32—C22—Cl33	122.3 (6)
C4—C9—H13	109 (2)	C18—C25—S34	119.1 (6)
C4—C9—H14	110 (3)	C18—C25—C35	120.9 (7)
C4—C9—H15	108 (2)	S34—C25—C35	120.0 (7)
H13—C9—H14	108 (3)	C19—C26—C35	121.3 (6)
H13—C9—H15	110 (3)	C19—C26—H36	117 (3)
H14—C9—H15	112 (4)	C35—C26—H36	121 (3)
N5—C11—C16	120.3 (7)	C21—C32—C22	121.8 (6)
N5—C11—C17	119.4 (6)	C21—C32—Cl37	118.9 (6)
C16—C11—C17	120.3 (7)	C22—C32—Cl37	119.3 (6)
N7—C12—C18	120.4 (6)	C25—S34—O38	106.1 (9)
N7—C12—C19	118.2 (6)	C25—S34—O39	107.8 (8)
C18—C12—C19	121.4 (7)	C25—S34—O40	105.6 (8)
C11—C16—S20	125.2 (6)	O38—S34—O39	114 (1)
C11—C16—C21	119.6 (6)	O38—S34—O40	110 (1)
S20—C16—C21	115.2 (5)	O39—S34—O40	113 (1)
C11—C17—C22	118.4 (5)	C25—C35—C26	119.2 (7)
C11—C17—H23	122 (3)	C25—C35—H41	118 (2)
C22—C17—H23	119 (3)	C26—C35—H41	122 (2)

(PY183beta)

Crystal data

C16H16CaCl2N4O10S2	Z = 2
Mr = 599.43	F(000) = 608
Triclinic, P1	Dx = 1.808 Mg m^−3
a = 5.574 (3) Å	Cu Kα radiation, λ = 1.54178 Å
b = 10.925 (3) Å	Cell parameters from 25 reflections
c = 18.801 (5) Å	θ = 2–115°
α = 98.605 (19)°	µ = 7.09 mm^−1
β = 92.35 (3)°	T = 203 K
γ = 102.77 (3)°	Needle, orange
V = 1100.8 (8) Å^3	0.40 × 0.02 × 0.02 mm

Data collection

Siemens P4 diffractometer	1925 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.073
Graphite monochromator	θmax = 55.4°, θmin = 2.4°
Absorption correction: difabsEmpirical(SHELXA) theta/2theta scan	h = −5→5
Tmin = 0.414, Tmax = 1.000	k = −11→11
3144 measured reflections	l = −20→20
2790 independent reflections

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)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.143	w = 1/[σ^2(Fo^2) + (0.0728P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.002
2790 reflections	Δρmax = 0.55 e Å^−3
347 parameters	Δρmin = −0.48 e Å^−3
11 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0004 (3)

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
S1	−0.2118 (3)	0.51677 (16)	−0.15157 (8)	0.0171 (5)
S2	0.6430 (3)	0.02825 (16)	−0.09751 (8)	0.0160 (5)
Cl1	−0.7209 (4)	0.5875 (2)	−0.44216 (10)	0.0434 (6)
Cl2	−0.8091 (3)	0.74322 (17)	−0.29333 (10)	0.0295 (5)
Ca	0.2484 (3)	0.21803 (13)	0.00759 (7)	0.0168 (4)
C1	−0.4205 (13)	0.4876 (7)	−0.3642 (4)	0.0225 (18)
H1	−0.3937	0.4424	−0.4086	0.05 (3)*
C2	−0.5752 (13)	0.5714 (7)	−0.3624 (4)	0.0241 (18)
C3	−0.6162 (13)	0.6380 (6)	−0.2973 (4)	0.0203 (17)
C4	−0.4997 (12)	0.6210 (6)	−0.2345 (4)	0.0190 (17)
H4	−0.5234	0.6684	−0.1904	0.002 (15)*
C5	−0.3507 (12)	0.5369 (6)	−0.2348 (4)	0.0179 (17)
C6	−0.3053 (12)	0.4699 (6)	−0.3011 (3)	0.0136 (15)
O7	−0.3142 (9)	0.5916 (4)	−0.0955 (2)	0.0236 (12)
O8	0.0516 (8)	0.5632 (5)	−0.1546 (3)	0.0263 (12)
O9	−0.2794 (10)	0.3816 (4)	−0.1473 (2)	0.0282 (13)
N10	−0.1453 (10)	0.3868 (5)	−0.3031 (3)	0.0201 (14)
H10	−0.0816	0.3708	−0.2634	0.04 (3)*
N11	−0.0937 (10)	0.3333 (5)	−0.3670 (3)	0.0195 (14)
C12	0.0656 (13)	0.2604 (6)	−0.3659 (3)	0.0178 (16)
C13	0.1870 (13)	0.2282 (6)	−0.3035 (4)	0.0182 (16)
O14	0.1690 (9)	0.2663 (5)	−0.2389 (2)	0.0263 (12)
N15	0.3288 (11)	0.1487 (6)	−0.3335 (3)	0.0213 (14)
N16	0.3027 (11)	0.1280 (6)	−0.4095 (3)	0.0267 (16)
C17	0.1483 (14)	0.1923 (7)	−0.4290 (4)	0.0239 (18)
C18	0.0786 (18)	0.1934 (9)	−0.5057 (4)	0.050 (3)
H18A	0.1143	0.2804	−0.5149	0.068 (18)*
H18B	−0.0963	0.1559	−0.5162	0.068 (18)*
H18C	0.1721	0.1446	−0.5362	0.068 (18)*
C19	0.4851 (12)	0.0838 (6)	−0.2987 (3)	0.0166 (16)
C20	0.4912 (12)	0.0885 (6)	−0.2243 (3)	0.0173 (16)
H20	0.3928	0.1338	−0.1965	0.03 (2)*
C21	0.6425 (12)	0.0263 (6)	−0.1919 (3)	0.0163 (16)
C22	0.7917 (13)	−0.0408 (7)	−0.2314 (3)	0.0230 (18)
H22	0.8967	−0.0817	−0.2084	0.016 (18)*
C23	0.7813 (14)	−0.0456 (7)	−0.3058 (4)	0.0234 (18)
H23	0.8782	−0.0919	−0.3335	0.05 (2)*
C24	0.6305 (13)	0.0166 (7)	−0.3397 (4)	0.0211 (17)
H24	0.6264	0.0135	−0.3899	0.04 (2)*
O25	0.4473 (9)	0.0905 (5)	−0.0740 (2)	0.0255 (12)
O26	0.8868 (9)	0.0938 (5)	−0.0652 (2)	0.0274 (12)
O27	0.5817 (9)	−0.1058 (4)	−0.0888 (2)	0.0235 (12)
O30	0.2142 (10)	0.3491 (5)	−0.0816 (3)	0.0297 (13)
H30A	0.288 (7)	0.350 (9)	−0.1191 (13)	0.08 (3)*
H30B	0.068 (4)	0.343 (10)	−0.095 (2)	0.08 (3)*
O31	−0.0541 (10)	0.1782 (5)	0.0942 (3)	0.0331 (13)
H31A	−0.117 (8)	0.2372 (16)	0.112 (2)	0.14 (4)*
H31B	−0.172 (6)	0.115 (3)	0.0842 (14)	0.14 (4)*
O32	0.6715 (10)	0.3446 (5)	0.0060 (3)	0.0314 (13)
H32A	0.704 (15)	0.412 (3)	0.036 (3)	0.05 (2)*
H32B	0.711 (15)	0.366 (6)	−0.0331 (17)	0.05 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0169 (11)	0.0219 (10)	0.0104 (9)	0.0022 (8)	0.0023 (7)	−0.0011 (7)
S2	0.0150 (10)	0.0218 (10)	0.0104 (9)	0.0052 (8)	0.0016 (7)	−0.0017 (7)
Cl1	0.0542 (15)	0.0633 (15)	0.0230 (11)	0.0381 (12)	−0.0036 (10)	0.0050 (10)
Cl2	0.0257 (11)	0.0296 (11)	0.0378 (11)	0.0150 (9)	0.0063 (9)	0.0057 (9)
Ca	0.0164 (8)	0.0185 (8)	0.0135 (8)	0.0021 (6)	0.0025 (6)	−0.0013 (6)
C1	0.030 (5)	0.023 (4)	0.016 (4)	0.011 (4)	0.004 (3)	0.000 (3)
C2	0.021 (5)	0.034 (5)	0.020 (4)	0.011 (4)	−0.003 (3)	0.005 (3)
C3	0.021 (4)	0.013 (4)	0.027 (4)	0.009 (3)	0.000 (3)	−0.001 (3)
C4	0.014 (4)	0.017 (4)	0.018 (4)	−0.005 (3)	0.005 (3)	−0.007 (3)
C5	0.011 (4)	0.023 (4)	0.020 (4)	0.001 (3)	0.005 (3)	0.006 (3)
C6	0.015 (4)	0.017 (4)	0.008 (3)	0.003 (3)	0.000 (3)	−0.001 (3)
O7	0.029 (3)	0.028 (3)	0.009 (2)	0.001 (2)	0.008 (2)	−0.005 (2)
O8	0.012 (3)	0.036 (3)	0.026 (3)	−0.003 (2)	0.002 (2)	0.002 (2)
O9	0.046 (4)	0.017 (3)	0.016 (3)	−0.001 (3)	−0.001 (2)	0.001 (2)
N10	0.018 (4)	0.030 (4)	0.012 (3)	0.008 (3)	0.003 (3)	0.000 (3)
N11	0.019 (3)	0.023 (3)	0.015 (3)	0.006 (3)	−0.001 (3)	−0.004 (3)
C12	0.017 (4)	0.024 (4)	0.012 (4)	0.008 (4)	−0.001 (3)	−0.005 (3)
C13	0.018 (4)	0.016 (4)	0.017 (4)	−0.001 (3)	−0.002 (3)	0.000 (3)
O14	0.036 (3)	0.034 (3)	0.012 (3)	0.019 (3)	0.000 (2)	−0.002 (2)
N15	0.024 (4)	0.031 (4)	0.011 (3)	0.013 (3)	0.000 (3)	−0.001 (3)
N16	0.036 (4)	0.039 (4)	0.011 (3)	0.023 (4)	0.003 (3)	−0.001 (3)
C17	0.030 (5)	0.033 (4)	0.015 (4)	0.021 (4)	0.004 (3)	−0.001 (3)
C18	0.077 (7)	0.074 (7)	0.014 (4)	0.062 (6)	−0.001 (4)	−0.004 (4)
C19	0.018 (4)	0.017 (4)	0.015 (4)	0.005 (3)	0.003 (3)	0.000 (3)
C20	0.014 (4)	0.020 (4)	0.015 (4)	0.002 (3)	0.009 (3)	−0.004 (3)
C21	0.017 (4)	0.016 (4)	0.013 (4)	0.000 (3)	0.005 (3)	−0.003 (3)
C22	0.030 (5)	0.032 (5)	0.012 (4)	0.017 (4)	0.003 (3)	0.004 (3)
C23	0.033 (5)	0.025 (4)	0.016 (4)	0.016 (4)	0.008 (3)	0.002 (3)
C24	0.026 (5)	0.029 (4)	0.011 (4)	0.013 (4)	0.004 (3)	0.002 (3)
O25	0.024 (3)	0.042 (3)	0.012 (3)	0.016 (3)	0.006 (2)	−0.002 (2)
O26	0.012 (3)	0.042 (3)	0.022 (3)	0.001 (2)	−0.008 (2)	−0.004 (2)
O27	0.029 (3)	0.025 (3)	0.017 (3)	0.006 (2)	0.005 (2)	0.005 (2)
O30	0.030 (3)	0.036 (3)	0.024 (3)	0.005 (3)	0.002 (2)	0.013 (3)
O31	0.022 (3)	0.033 (3)	0.035 (3)	−0.008 (3)	0.008 (3)	−0.006 (3)
O32	0.034 (4)	0.034 (3)	0.024 (3)	0.007 (3)	0.008 (3)	−0.002 (3)

Geometric parameters (Å, º)

S1—O8	1.450 (5)	C5—C6	1.411 (9)
S1—O7	1.450 (4)	C6—N10	1.404 (8)
S1—O9	1.456 (5)	O7—Ca^ii	2.404 (5)
S1—C5	1.781 (7)	N10—N11	1.326 (7)
S2—O26	1.450 (5)	N11—C12	1.319 (8)
S2—O25	1.458 (5)	C12—C17	1.450 (9)
S2—O27	1.464 (5)	C12—C13	1.457 (9)
S2—C21	1.772 (6)	C13—O14	1.239 (8)
Cl1—C2	1.727 (7)	C13—N15	1.375 (8)
Cl2—C3	1.735 (6)	N15—N16	1.410 (7)
Ca—O27^i	2.385 (5)	N15—C19	1.433 (9)
Ca—O25	2.388 (4)	N16—C17	1.298 (9)
Ca—O30	2.390 (5)	C17—C18	1.481 (10)
Ca—O7^ii	2.404 (5)	C19—C24	1.390 (9)
Ca—O26^iii	2.405 (5)	C19—C20	1.392 (9)
Ca—O31	2.408 (5)	C20—C21	1.371 (9)
Ca—O32	2.460 (6)	C21—C22	1.392 (9)
C1—C6	1.384 (9)	C22—C23	1.390 (9)
C1—C2	1.388 (9)	C23—C24	1.383 (9)
C2—C3	1.381 (10)	O26—Ca^iv	2.405 (5)
C3—C4	1.381 (9)	O27—Ca^i	2.385 (5)
C4—C5	1.367 (9)
O8—S1—O7	113.1 (3)	C4—C3—Cl2	119.6 (5)
O8—S1—O9	112.5 (3)	C2—C3—Cl2	121.2 (5)
O7—S1—O9	111.8 (3)	C5—C4—C3	121.7 (6)
O8—S1—C5	105.9 (3)	C4—C5—C6	119.3 (6)
O7—S1—C5	105.8 (3)	C4—C5—S1	119.5 (5)
O9—S1—C5	107.1 (3)	C6—C5—S1	121.2 (5)
O26—S2—O25	114.1 (3)	C1—C6—N10	120.6 (6)
O26—S2—O27	112.3 (3)	C1—C6—C5	118.9 (6)
O25—S2—O27	110.8 (3)	N10—C6—C5	120.5 (6)
O26—S2—C21	108.2 (3)	S1—O7—Ca^ii	147.0 (3)
O25—S2—C21	105.7 (3)	N11—N10—C6	118.3 (6)
O27—S2—C21	105.1 (3)	C12—N11—N10	115.9 (6)
O27^i—Ca—O25	79.50 (16)	N11—C12—C17	125.5 (6)
O27^i—Ca—O30	161.54 (18)	N11—C12—C13	128.2 (6)
O25—Ca—O30	90.03 (18)	C17—C12—C13	106.3 (6)
O27^i—Ca—O7^ii	92.76 (17)	O14—C13—N15	128.7 (6)
O25—Ca—O7^ii	144.15 (18)	O14—C13—C12	127.7 (6)
O30—Ca—O7^ii	86.87 (18)	N15—C13—C12	103.6 (5)
O27^i—Ca—O26^iii	114.27 (18)	C13—N15—N16	112.3 (5)
O25—Ca—O26^iii	81.96 (17)	C13—N15—C19	129.4 (5)
O30—Ca—O26^iii	78.77 (18)	N16—N15—C19	118.2 (5)
O7^ii—Ca—O26^iii	131.98 (17)	C17—N16—N15	107.6 (5)
O27^i—Ca—O31	74.88 (18)	N16—C17—C12	110.2 (6)
O25—Ca—O31	135.67 (18)	N16—C17—C18	122.3 (6)
O30—Ca—O31	122.34 (19)	C12—C17—C18	127.5 (6)
O7^ii—Ca—O31	73.22 (16)	C24—C19—C20	120.4 (6)
O26^iii—Ca—O31	76.59 (17)	C24—C19—N15	119.7 (6)
O27^i—Ca—O32	86.34 (18)	C20—C19—N15	119.9 (6)
O25—Ca—O32	74.37 (17)	C21—C20—C19	119.1 (6)
O30—Ca—O32	76.15 (19)	C20—C21—C22	121.8 (6)
O7^ii—Ca—O32	70.21 (16)	C20—C21—S2	119.1 (5)
O26^iii—Ca—O32	145.21 (17)	C22—C21—S2	119.1 (5)
O31—Ca—O32	137.73 (17)	C23—C22—C21	118.3 (6)
C6—C1—C2	120.6 (6)	C24—C23—C22	120.9 (6)
C3—C2—C1	120.1 (6)	C23—C24—C19	119.5 (6)
C3—C2—Cl1	120.9 (5)	S2—O25—Ca	155.9 (3)
C1—C2—Cl1	119.0 (5)	S2—O26—Ca^iv	168.8 (3)
C4—C3—C2	119.2 (6)	S2—O27—Ca^i	131.6 (3)
C6—C1—C2—C3	−0.2 (11)	N15—N16—C17—C18	179.5 (8)
C6—C1—C2—Cl1	−178.4 (6)	N11—C12—C17—N16	−179.2 (7)
C1—C2—C3—C4	0.7 (11)	C13—C12—C17—N16	−0.9 (9)
Cl1—C2—C3—C4	178.9 (6)	N11—C12—C17—C18	1.9 (13)
C1—C2—C3—Cl2	−179.9 (6)	C13—C12—C17—C18	−179.8 (8)
Cl1—C2—C3—Cl2	−1.7 (9)	C13—N15—C19—C24	−174.1 (7)
C2—C3—C4—C5	−2.1 (11)	N16—N15—C19—C24	8.4 (10)
Cl2—C3—C4—C5	178.4 (5)	C13—N15—C19—C20	5.7 (11)
C3—C4—C5—C6	2.9 (10)	N16—N15—C19—C20	−171.7 (6)
C3—C4—C5—S1	−178.5 (5)	C24—C19—C20—C21	0.1 (10)
O8—S1—C5—C4	−114.4 (6)	N15—C19—C20—C21	−179.7 (6)
O7—S1—C5—C4	5.8 (6)	C19—C20—C21—C22	0.5 (10)
O9—S1—C5—C4	125.3 (6)	C19—C20—C21—S2	−178.1 (5)
O8—S1—C5—C6	64.1 (6)	O26—S2—C21—C20	−116.7 (6)
O7—S1—C5—C6	−175.6 (5)	O25—S2—C21—C20	6.0 (6)
O9—S1—C5—C6	−56.2 (6)	O27—S2—C21—C20	123.2 (6)
C2—C1—C6—N10	−178.8 (6)	O26—S2—C21—C22	64.7 (6)
C2—C1—C6—C5	1.0 (10)	O25—S2—C21—C22	−172.6 (6)
C4—C5—C6—C1	−2.4 (10)	O27—S2—C21—C22	−55.4 (6)
S1—C5—C6—C1	179.1 (5)	C20—C21—C22—C23	−1.2 (11)
C4—C5—C6—N10	177.5 (6)	S2—C21—C22—C23	177.4 (6)
S1—C5—C6—N10	−1.0 (9)	C21—C22—C23—C24	1.3 (11)
O8—S1—O7—Ca^ii	10.4 (6)	C22—C23—C24—C19	−0.8 (11)
O9—S1—O7—Ca^ii	138.6 (5)	C20—C19—C24—C23	0.0 (11)
C5—S1—O7—Ca^ii	−105.1 (5)	N15—C19—C24—C23	179.9 (7)
C1—C6—N10—N11	4.8 (9)	O26—S2—O25—Ca	−29.4 (9)
C5—C6—N10—N11	−175.0 (6)	O27—S2—O25—Ca	98.6 (8)
C6—N10—N11—C12	177.2 (6)	C21—S2—O25—Ca	−148.1 (7)
N10—N11—C12—C17	179.8 (7)	O27^i—Ca—O25—S2	−39.7 (8)
N10—N11—C12—C13	1.9 (11)	O30—Ca—O25—S2	125.0 (8)
N11—C12—C13—O14	−2.2 (12)	O7^ii—Ca—O25—S2	40.3 (9)
C17—C12—C13—O14	179.6 (7)	O26^iii—Ca—O25—S2	−156.3 (8)
N11—C12—C13—N15	179.1 (7)	O31—Ca—O25—S2	−95.0 (8)
C17—C12—C13—N15	0.9 (8)	O32—Ca—O25—S2	49.4 (8)
O14—C13—N15—N16	−179.3 (7)	O25—S2—O26—Ca^iv	26.8 (18)
C12—C13—N15—N16	−0.6 (8)	O27—S2—O26—Ca^iv	−100.4 (17)
O14—C13—N15—C19	3.1 (12)	C21—S2—O26—Ca^iv	144.1 (17)
C12—C13—N15—C19	−178.2 (7)	O26—S2—O27—Ca^i	18.9 (4)
C13—N15—N16—C17	0.1 (8)	O25—S2—O27—Ca^i	−110.0 (4)
C19—N15—N16—C17	177.9 (6)	C21—S2—O27—Ca^i	136.2 (3)
N15—N16—C17—C12	0.5 (9)

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

(PY191alpha)

Crystal data

C17H15CaClN4O8S2	Z = 2
Mr = 543.0	F(000) = 556
Triclinic, P1	Dx = 1.735 Mg m^−3
Hall symbol: -P 1	Cu Kα1 radiation, λ = 1.54056 Å
a = 5.6915 (2) Å	µ = 6.19 mm^−1
b = 10.6053 (3) Å	T = 293 K
c = 18.5569 (6) Å	Particle morphology: no specific habit
α = 72.828 (2)°	yellow
β = 88.271 (2)°	cylinder, 10 × 0.7 mm
γ = 76.423 (1)°	Specimen preparation: Prepared at 293 K and 0.00 kPa
V = 1039.37 (5) Å^3

Data collection

STOE-Stadi-P diffractometer	Data collection mode: transmission
Radiation source: sealed X-ray tube, laboratory diffractometer	Scan method: step
Primary focussing, Ge 111 monochromator	2θmin = 2.00°, 2θmax = 70.00°, 2θstep = 0.01°
Specimen mounting: 'glass capillary'

Refinement

Refinement on Inet	187 parameters
Least-squares matrix: full with fixed elements per cycle	126 restraints
Rp = 0.091	0 constraints
Rwp = 0.100	H-atom parameters not refined
Rexp = 0.055	Weighting scheme based on measured s.u.'s w = 1/σ[Yobs]^2
χ^2 = 1.839	(Δ/σ)max = 0.001
6800 data points	Background function: Chebyshev polynomial with 10 terms
Profile function: modified Thompson-Cox-Hastings pseudo-Voigt (Young, 1993)	Preferred orientation correction: none

Special details

Experimental. specimen was rotated in its plane

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

	x	y	z	Biso*/Beq
C1	1.0709 (7)	−0.8158 (4)	0.1361 (3)	2.00 (10)
N2	0.9266 (9)	−0.8949 (5)	0.1371 (3)	2.00 (10)
C3	1.1964 (7)	−0.8037 (3)	0.2021 (2)	2.00 (10)
C4	1.1462 (8)	−0.7194 (4)	0.0700 (2)	2.00 (10)
N5	0.8652 (9)	−0.9595 (5)	0.2053 (3)	2.00 (10)
O6	1.1863 (10)	−0.8649 (5)	0.2677 (3)	2.00 (10)
N7	1.3271 (6)	−0.7061 (4)	0.1698 (3)	2.00 (10)
N8	1.2951 (7)	−0.6553 (4)	0.0897 (3)	2.00 (10)
C9	1.0714 (8)	−0.6911 (4)	−0.0113 (2)	2.00 (10)
H10	0.945 (5)	−0.969 (2)	0.2447 (13)	2.40 (12)
C11	0.7087 (8)	−1.0451 (4)	0.2067 (3)	2.00 (10)
C12	1.4754 (7)	−0.6537 (4)	0.2064 (3)	2.00 (10)
H13	1.067 (5)	−0.595 (2)	−0.0377 (13)	2.40 (12)
H14	0.911 (5)	−0.708 (2)	−0.0158 (15)	2.40 (12)
H15	1.189 (5)	−0.751 (2)	−0.0329 (15)	2.40 (12)
C16	0.6784 (8)	−1.1386 (4)	0.2753 (2)	2.00 (10)
C17	0.5807 (8)	−1.0383 (4)	0.1391 (2)	2.00 (10)
C18	1.4589 (7)	−0.6733 (3)	0.2830 (3)	2.00 (10)
C19	1.6290 (8)	−0.5797 (4)	0.1635 (3)	2.00 (10)
S20	0.8273 (7)	−1.1601 (4)	0.3636 (2)	2.00 (10)
C21	0.5261 (7)	−1.2231 (4)	0.2778 (2)	2.00 (10)
C22	0.4301 (7)	−1.1256 (4)	0.1446 (3)	2.00 (10)
H23	0.594 (4)	−0.976 (3)	0.0900 (13)	2.40 (12)
H24	1.352 (5)	−0.723 (3)	0.3112 (14)	2.40 (12)
C25	1.6050 (9)	−0.6184 (4)	0.3187 (3)	2.00 (10)
C26	1.7744 (9)	−0.5245 (4)	0.1990 (3)	2.00 (10)
H27	1.634 (5)	−0.568 (2)	0.1103 (13)	2.40 (12)
O28	0.6528 (15)	−1.0734 (9)	0.3983 (5)	2.00 (10)
O29	1.0343 (13)	−1.1049 (9)	0.3442 (6)	2.00 (10)
O30	0.8693 (18)	−1.3027 (7)	0.4019 (5)	2.00 (10)
H31	0.512 (5)	−1.285 (2)	0.3258 (13)	2.40 (12)
C32	0.4017 (8)	−1.2168 (4)	0.2123 (3)	2.00 (10)
Cl33	0.2846 (9)	−1.1153 (4)	0.0632 (2)	2.5 (2)
S34	1.5785 (7)	−0.6466 (4)	0.4189 (2)	2.00 (10)
C35	1.7620 (8)	−0.5447 (4)	0.2777 (3)	2.00 (10)
H36	1.879 (5)	−0.475 (2)	0.1697 (13)	2.40 (12)
C37	0.2334 (8)	−1.3065 (4)	0.2126 (3)	2.00 (10)
O38	1.6086 (19)	−0.7919 (7)	0.4528 (5)	2.00 (10)
O39	1.7466 (14)	−0.5872 (8)	0.4457 (5)	2.00 (10)
O40	1.3326 (13)	−0.5803 (10)	0.4286 (6)	2.00 (10)
H41	1.859 (5)	−0.510 (2)	0.3037 (13)	2.40 (12)
Ca1	1	−1.5	0.5	2.00 (10)
Ca2	0.5	−1	0.5	2.00 (10)
O44	0.869 (2)	−1.0896 (12)	0.5807 (7)	2.00 (10)
H45	1.01098	−1.11626	0.55218	2.40 (12)
H46	0.86322	−1.0578	0.62213	2.40 (12)
H47	0.140 (5)	−1.315 (2)	0.2581 (13)	2.40 (12)
H48	0.324 (5)	−1.397 (2)	0.2111 (14)	2.40 (12)
H49	0.128 (5)	−1.265 (2)	0.1682 (14)	2.40 (12)

Geometric parameters (Å, º)

C1—N2	1.301 (7)	C16—C21	1.376 (7)
C1—C3	1.489 (6)	C17—C22	1.383 (7)
C1—C4	1.472 (5)	C17—H23	0.97 (2)
N2—N5	1.329 (7)	C18—H24	0.94 (3)
C3—O6	1.205 (7)	C18—C25	1.400 (7)
C3—N7	1.397 (5)	C19—C26	1.397 (7)
C4—N8	1.323 (7)	C19—H27	0.96 (2)
C4—C9	1.503 (6)	S20—O28	1.46 (1)
N5—H10	0.84 (3)	S20—O29	1.43 (1)
N5—C11	1.408 (7)	S20—O30	1.43 (1)
N7—N8	1.425 (7)	C21—H31	0.95 (2)
N7—C12	1.400 (6)	C21—C32	1.401 (7)
C9—H13	0.99 (2)	C22—C32	1.373 (6)
C9—H14	0.98 (3)	C22—Cl33	1.707 (7)
C9—H15	0.97 (2)	C25—S34	1.800 (6)
C37—H47	0.98 (2)	C25—C35	1.388 (7)
C37—H48	0.98 (2)	C26—C35	1.414 (7)
C37—H49	0.96 (2)	C26—H36	0.94 (2)
C11—C16	1.398 (5)	C32—C37	1.499 (7)
C11—C17	1.444 (7)	S34—O38	1.452 (8)
C12—C18	1.378 (7)	S34—O39	1.43 (1)
C12—C19	1.387 (6)	S34—O40	1.443 (8)
C16—S20	1.796 (6)	C35—H41	0.94 (3)
N2—C1—C3	127.2 (4)	C11—C17—C22	118.3 (4)
N2—C1—C4	127.8 (5)	C11—C17—H23	124 (2)
C3—C1—C4	105.0 (3)	C22—C17—H23	118 (2)
C1—N2—N5	115.2 (5)	C12—C18—H24	121 (2)
C1—C3—O6	127.5 (5)	C12—C18—C25	118.7 (4)
C1—C3—N7	103.6 (3)	H24—C18—C25	120 (2)
O6—C3—N7	128.9 (5)	C12—C19—C26	119.1 (4)
C1—C4—N8	111.7 (4)	C12—C19—H27	120 (2)
C1—C4—C9	127.1 (4)	C26—C19—H27	121 (2)
N8—C4—C9	121.2 (4)	C16—S20—O28	103.4 (4)
N2—N5—H10	122 (2)	C16—S20—O29	105.4 (5)
N2—N5—C11	115.5 (5)	C16—S20—O30	104.6 (5)
H10—N5—C11	120 (2)	O28—S20—O29	109.6 (6)
C3—N7—N8	113.2 (4)	O28—S20—O30	114.8 (6)
C3—N7—C12	128.1 (4)	O29—S20—O30	117.3 (6)
N8—N7—C12	118.7 (3)	C16—C21—H31	116 (2)
C4—N8—N7	106.4 (3)	C16—C21—C32	120.8 (4)
C4—C9—H13	108 (1)	H31—C21—C32	123 (2)
C4—C9—H14	111 (2)	C17—C22—C32	121.3 (4)
C4—C9—H15	108 (1)	C17—C22—Cl33	116.8 (3)
H13—C9—H14	109 (2)	C18—C25—S34	117.4 (4)
H13—C9—H15	111 (2)	C18—C25—C35	120.6 (4)
H14—C9—H15	109 (2)	S34—C25—C35	122.0 (4)
C32—C37—H47	109 (2)	C19—C26—C35	119.5 (4)
C32—C37—H48	111 (2)	C19—C26—H36	119 (2)
C32—C37—H49	108 (2)	C35—C26—H36	121 (2)
H47—C37—H48	110 (2)	C21—C32—C22	120.2 (4)
H47—C37—H49	110 (2)	C21—C32—C37	122.5 (4)
H48—C37—H49	109 (2)	C22—C32—C37	117.3 (4)
N5—C11—C16	118.7 (4)	C25—S34—O38	106.7 (5)
N5—C11—C17	121.4 (4)	C25—S34—O39	109.3 (4)
C16—C11—C17	119.9 (4)	C25—S34—O40	105.6 (4)
N7—C12—C18	119.2 (4)	O38—S34—O39	115.7 (6)
N7—C12—C19	118.5 (4)	O38—S34—O40	108.1 (6)
C18—C12—C19	122.2 (4)	O39—S34—O40	110.8 (6)
C11—C16—S20	124.9 (4)	C25—C35—C26	119.7 (5)
C11—C16—C21	119.5 (4)	C25—C35—H41	118 (1)
S20—C16—C21	115.5 (3)	C26—C35—H41	122 (1)

(PY191beta)

Crystal data

C17H19CaClN4O10S2	V = 1136.55 (3) Å^3
Mr = 579.03	Z = 2
Triclinic, P1	F(000) = 596
Hall symbol: -P 1	Dx = 1.692 Mg m^−3
a = 6.0140 (1) Å	Synchrotron radiation, λ = 0.649819 Å
b = 10.8169 (2) Å	T = 293 K
c = 18.0938 (3) Å	Particle morphology: no specific habit
α = 85.677 (1)°	yellow
β = 86.392 (1)°	cylinder, 10 × 0.7 mm
γ = 75.783 (1)°	Specimen preparation: Prepared at 293 K and 0.00 kPa

Data collection

NSLS Brookhaven diffractometer	Scan method: step
Specimen mounting: glass capillary	2θmin = 1.000°, 2θmax = 20.896°, 2θstep = 0.003°
Data collection mode: step

Refinement

Refinement on Inet	207 parameters
Least-squares matrix: full with fixed elements per cycle	126 restraints
Rp = 0.095	0 constraints
Rwp = 0.122	H-atom parameters not refined
Rexp = 0.206	Weighting scheme based on measured s.u.'s w = 1/σ[Yobs]^2
χ^2 = 0.591
6633 data points	Background function: Chebyshev polynomial with 20 terms
Profile function: modified Thompson-Cox-Hastings pseudo-Voigt (Young, 1993)	Preferred orientation correction: none

Special details

Experimental. specimen was rotated in its plane

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

	x	y	z	Biso*/Beq
C1	−0.0178 (8)	0.7603 (4)	−0.6354 (3)	2.77 (9)
N2	0.1250 (10)	0.8335 (6)	−0.6389 (4)	2.77 (9)
C3	−0.1347 (7)	0.7208 (4)	−0.6947 (3)	2.77 (9)
C4	−0.0965 (8)	0.6984 (4)	−0.5689 (3)	2.77 (9)
N5	0.1916 (10)	0.8755 (6)	−0.7063 (3)	2.77 (9)
O6	−0.1194 (11)	0.7511 (6)	−0.7599 (4)	2.77 (9)
N7	−0.2656 (8)	0.6434 (4)	−0.6597 (3)	2.77 (9)
N8	−0.2413 (8)	0.6292 (4)	−0.5808 (4)	2.77 (9)
C9	−0.0246 (9)	0.7101 (4)	−0.4946 (3)	2.77 (9)
H10	0.122 (5)	0.867 (3)	−0.7470 (16)	3.32 (11)
C11	0.3434 (8)	0.9539 (5)	−0.7104 (3)	2.77 (9)
C12	−0.4096 (8)	0.5787 (4)	−0.6907 (3)	2.77 (9)
H13	−0.085 (5)	0.652 (3)	−0.4600 (17)	3.32 (11)
H14	−0.086 (6)	0.802 (3)	−0.4822 (17)	3.32 (11)
H15	0.145 (5)	0.685 (3)	−0.4956 (18)	3.32 (11)
C16	0.4035 (8)	1.0082 (5)	−0.7786 (3)	2.77 (9)
C17	0.4353 (9)	0.9791 (5)	−0.6452 (3)	2.77 (9)
C18	−0.4096 (9)	0.5706 (5)	−0.7671 (3)	2.77 (9)
C19	−0.5470 (9)	0.5200 (5)	−0.6433 (3)	2.77 (9)
S20	0.3001 (7)	0.9802 (4)	−0.8647 (3)	2.77 (9)
C21	0.5545 (9)	1.0876 (4)	−0.7815 (3)	2.77 (9)
C22	0.5842 (8)	1.0586 (4)	−0.6520 (3)	2.77 (9)
H23	0.397 (5)	0.941 (3)	−0.5964 (16)	3.32 (11)
H24	−0.317 (5)	0.610 (3)	−0.7999 (16)	3.32 (11)
C25	−0.5491 (9)	0.5039 (4)	−0.7950 (3)	2.77 (9)
C26	−0.6859 (8)	0.4531 (4)	−0.6742 (3)	2.77 (9)
H27	−0.547 (6)	0.527 (3)	−0.5908 (16)	3.32 (11)
O28	0.0572 (13)	0.9968 (10)	−0.8496 (6)	2.77 (9)
O29	0.3615 (16)	1.0695 (8)	−0.9203 (5)	2.77 (9)
O30	0.4155 (18)	0.8489 (8)	−0.8782 (6)	2.77 (9)
H31	0.592 (5)	1.123 (3)	−0.8285 (16)	3.32 (11)
C32	0.6495 (7)	1.1153 (4)	−0.7187 (3)	2.77 (9)
Cl33	0.6947 (8)	1.0890 (4)	−0.5699 (3)	2.77 (9)
S34	−0.5517 (8)	0.4963 (4)	−0.8927 (3)	2.77 (9)
C35	−0.6859 (9)	0.4460 (5)	−0.7493 (3)	2.77 (9)
H36	−0.780 (5)	0.412 (3)	−0.6433 (17)	3.32 (11)
C37	0.8099 (9)	1.1977 (5)	−0.7189 (3)	2.77 (9)
O38	−0.4032 (15)	0.5747 (9)	−0.9265 (6)	2.77 (9)
O39	−0.7857 (14)	0.5556 (10)	−0.9117 (6)	2.77 (9)
O40	−0.4819 (19)	0.3631 (8)	−0.9073 (6)	2.77 (9)
H41	−0.776 (6)	0.403 (3)	−0.7698 (16)	3.32 (11)
H42	0.842 (6)	1.231 (3)	−0.7684 (16)	3.32 (11)
H43	0.948 (5)	1.145 (3)	−0.6991 (15)	3.32 (11)
H44	0.744 (6)	1.267 (3)	−0.6871 (16)	3.32 (11)
Ca45	0.4161 (9)	1.2368 (5)	−1.0014 (3)	2.77 (9)
O46	0.802 (2)	1.1298 (11)	−0.9767 (7)	2.77 (9)
O47	0.119 (2)	1.2093 (11)	−1.0786 (7)	2.77 (9)
O48	0.055 (2)	1.3425 (10)	−0.9393 (7)	2.77 (9)
H49	0.9057	1.1542	−1.0113	3.32 (11)
H50	0.9047	1.0778	−0.9351	3.32 (11)
H51	0.1037	1.2234	−1.1387	3.32 (11)
H52	−0.0221	1.3046	−1.0768	3.32 (11)
H53	0.02747	1.43491	−0.92132	3.32 (11)
H54	−0.09142	1.30966	−0.93053	3.32 (11)

Geometric parameters (Å, º)

C1—N2	1.299 (8)	C18—H24	0.93 (3)
C1—C3	1.464 (8)	C18—C25	1.373 (8)
C1—C4	1.443 (7)	C19—C26	1.397 (8)
N2—N5	1.342 (9)	C19—H27	0.96 (3)
C3—O6	1.204 (9)	S20—O28	1.438 (9)
C3—N7	1.380 (7)	S20—O29	1.44 (1)
C4—N8	1.317 (7)	S20—O30	1.452 (9)
C4—C9	1.460 (8)	C21—H31	0.94 (3)
N5—H10	0.89 (3)	C21—C32	1.387 (8)
N5—C11	1.385 (9)	C22—C32	1.392 (8)
N7—N8	1.436 (9)	C22—Cl33	1.749 (8)
N7—C12	1.405 (7)	C25—S34	1.777 (8)
C9—H13	0.97 (3)	C25—C35	1.358 (8)
C9—H14	1.01 (3)	C26—C35	1.367 (8)
C9—H15	0.99 (3)	C26—H36	0.94 (3)
C11—C16	1.392 (8)	C32—C37	1.465 (7)
C11—C17	1.406 (8)	S34—O38	1.45 (1)
C12—C18	1.391 (8)	S34—O39	1.447 (9)
C12—C19	1.381 (7)	S34—O40	1.437 (9)
C16—S20	1.786 (8)	C35—H41	0.91 (3)
C16—C21	1.391 (8)	C37—H42	0.96 (3)
C17—C22	1.380 (8)	C37—H43	0.96 (3)
C17—H23	0.98 (3)	C37—H44	0.97 (3)
N2—C1—C3	129.8 (5)	C12—C19—C26	118.2 (5)
N2—C1—C4	126.1 (6)	C12—C19—H27	120 (2)
C3—C1—C4	104.1 (4)	C26—C19—H27	122 (2)
C1—N2—N5	117.8 (6)	C16—S20—O28	103.8 (5)
C1—C3—O6	126.7 (5)	C16—S20—O29	107.8 (5)
C1—C3—N7	105.2 (4)	C16—S20—O30	104.7 (5)
O6—C3—N7	128.1 (6)	O28—S20—O29	114.8 (6)
C1—C4—N8	113.8 (5)	O28—S20—O30	112.3 (7)
C1—C4—C9	124.0 (5)	O29—S20—O30	112.4 (6)
N8—C4—C9	122.2 (5)	C16—C21—C32	122.5 (5)
N2—N5—H10	121 (2)	H31—C21—C32	120 (2)
N2—N5—C11	118.0 (6)	C17—C22—C32	124.6 (5)
H10—N5—C11	119 (2)	C17—C22—Cl33	116.6 (5)
C3—N7—N8	112.4 (5)	C32—C22—Cl33	118.8 (4)
C3—N7—C12	129.0 (5)	C18—C25—S34	118.9 (4)
N8—N7—C12	118.5 (4)	C18—C25—C35	121.0 (6)
C4—N8—N7	104.4 (5)	S34—C25—C35	120.1 (5)
C4—C9—H13	108 (2)	C19—C26—C35	120.9 (5)
C4—C9—H14	107 (2)	C35—C26—H36	119 (2)
C4—C9—H15	108 (2)	C21—C32—C22	115.8 (5)
H13—C9—H14	112 (2)	C21—C32—C37	124.6 (5)
H13—C9—H15	109 (2)	C22—C32—C37	119.6 (5)
H14—C9—H15	112 (3)	C25—S34—O38	107.2 (6)
N5—C11—C16	120.2 (5)	C25—S34—O39	105.2 (5)
N5—C11—C17	119.6 (5)	C25—S34—O40	106.5 (5)
C16—C11—C17	120.1 (5)	O38—S34—O39	108.6 (6)
N7—C12—C18	121.0 (5)	O38—S34—O40	115.4 (6)
N7—C12—C19	118.3 (5)	O39—S34—O40	113.2 (7)
C18—C12—C19	120.6 (5)	C25—C35—C26	120.1 (5)
C11—C16—S20	123.5 (5)	C25—C35—H41	118 (2)
C11—C16—C21	119.4 (5)	C26—C35—H41	121 (2)
S20—C16—C21	117.0 (4)	C32—C37—H42	111 (2)
C11—C17—C22	117.5 (5)	C32—C37—H43	106 (2)
C11—C17—H23	122 (2)	C32—C37—H44	108 (2)
C22—C17—H23	120 (2)	H42—C37—H43	110 (2)
C12—C18—H24	122 (2)	H42—C37—H44	111 (2)
C12—C18—C25	119.2 (5)	H43—C37—H44	111 (2)
H24—C18—C25	119 (2)

(PY1833DMF)

Crystal data

C25H31CaCl2N7O10S2	Z = 2
Mr = 764.67	F(000) = 792
Triclinic, P1	Dx = 1.544 Mg m^−3
a = 10.5951 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.4600 (11) Å	Cell parameters from 12488 reflections
c = 15.2829 (15) Å	θ = 2.8–27.0°
α = 82.876 (8)°	µ = 0.55 mm^−1
β = 70.639 (8)°	T = 100 K
γ = 70.015 (7)°	Block, red
V = 1645.2 (3) Å^3	0.34 × 0.24 × 0.15 mm

Data collection

STOE IPDS II two-circle- diffractometer	7067 independent reflections
Radiation source: fine-focus sealed tube	4933 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
ω scans	θmax = 27.6°, θmin = 2.8°
Absorption correction: multi-scan MULABS (Spek, 1990; Blessing, 1995)	h = −13→13
Tmin = 0.837, Tmax = 0.923	k = −14→14
18279 measured reflections	l = −19→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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.054	H atoms treated by a mixture of independent and constrained refinement
S = 0.80	w = 1/[σ^2(Fo^2) + (0.0223P)^2] where P = (Fo^2 + 2Fc^2)/3
7067 reflections	(Δ/σ)max = 0.001
435 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

Special details

Experimental.

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
N1	0.73155 (14)	0.52321 (14)	0.57244 (10)	0.0187 (3)
H1	0.7339 (19)	0.5107 (19)	0.6293 (15)	0.022 (5)*
N2	0.82816 (14)	0.45643 (14)	0.50175 (10)	0.0186 (3)
C11	0.60727 (16)	0.60759 (16)	0.55834 (11)	0.0178 (3)
C12	0.50419 (16)	0.68635 (16)	0.62921 (11)	0.0180 (3)
S12	0.52317 (4)	0.69244 (4)	0.74036 (3)	0.01750 (9)
O121	0.60383 (12)	0.56670 (12)	0.75968 (8)	0.0244 (3)
O122	0.59342 (13)	0.78252 (13)	0.73256 (9)	0.0258 (3)
O123	0.37792 (12)	0.73077 (13)	0.80206 (8)	0.0264 (3)
C13	0.38123 (17)	0.76729 (17)	0.61311 (12)	0.0198 (4)
H13	0.3109	0.8206	0.6610	0.024*
C14	0.36101 (17)	0.77033 (17)	0.52730 (12)	0.0207 (4)
Cl14	0.20855 (4)	0.87511 (5)	0.50937 (3)	0.02927 (11)
C15	0.46227 (17)	0.69197 (17)	0.45816 (12)	0.0208 (4)
Cl15	0.43947 (5)	0.69113 (5)	0.35116 (3)	0.02752 (11)
C16	0.58482 (17)	0.60997 (17)	0.47279 (12)	0.0199 (4)
H16	0.6533	0.5556	0.4249	0.024*
C21	0.93837 (16)	0.37090 (17)	0.51655 (11)	0.0185 (3)
C22	0.97229 (17)	0.33594 (17)	0.60417 (12)	0.0207 (4)
O22	0.90382 (12)	0.38050 (13)	0.68106 (8)	0.0272 (3)
N23	1.09914 (14)	0.24177 (14)	0.57859 (10)	0.0206 (3)
N24	1.14755 (14)	0.21486 (14)	0.48272 (10)	0.0209 (3)
C25	1.05345 (16)	0.29063 (17)	0.44668 (12)	0.0195 (4)
C26	1.06731 (18)	0.28886 (19)	0.34684 (12)	0.0260 (4)
H26A	1.1540	0.2234	0.3158	0.039*
H26B	1.0714	0.3694	0.3182	0.039*
H26C	0.9856	0.2726	0.3407	0.039*
C31	1.18796 (16)	0.17756 (16)	0.63340 (11)	0.0183 (3)
C32	1.13262 (16)	0.17560 (16)	0.72994 (11)	0.0177 (3)
H32	1.0356	0.2172	0.7603	0.021*
S33	1.16355 (4)	0.11008 (4)	0.90373 (3)	0.01587 (9)
C33	1.22376 (16)	0.11085 (16)	0.78069 (11)	0.0162 (3)
O331	1.22120 (12)	0.19110 (12)	0.93268 (8)	0.0232 (3)
O332	1.00945 (11)	0.15370 (12)	0.93222 (8)	0.0216 (3)
O333	1.22041 (11)	−0.01935 (11)	0.93198 (8)	0.0195 (3)
C34	1.36536 (16)	0.04914 (17)	0.73759 (12)	0.0201 (4)
H34	1.4255	0.0050	0.7734	0.024*
C35	1.41820 (16)	0.05256 (17)	0.64175 (12)	0.0213 (4)
H35	1.5152	0.0106	0.6117	0.026*
C36	1.33037 (17)	0.11698 (17)	0.58889 (12)	0.0200 (4)
H36	1.3673	0.1196	0.5232	0.024*
Ca1	0.17752 (3)	0.79601 (3)	0.92653 (2)	0.01493 (7)
O1A	0.03429 (13)	0.89921 (13)	0.83141 (9)	0.0275 (3)
C1A	−0.09423 (19)	0.92437 (19)	0.84638 (13)	0.0261 (4)
H1A	−0.1459	0.8950	0.9030	0.031*
N1A	−0.16575 (14)	0.98896 (15)	0.78995 (11)	0.0237 (3)
C2A	−0.0976 (2)	1.0369 (2)	0.70151 (15)	0.0372 (5)
H2A1	0.0039	1.0132	0.6923	0.056*
H2A2	−0.1378	1.1276	0.7005	0.056*
H2A3	−0.1127	1.0023	0.6517	0.056*
C3A	−0.31730 (19)	1.0117 (2)	0.81320 (16)	0.0380 (5)
H3A1	−0.3522	0.9772	0.8750	0.057*
H3A2	−0.3351	0.9718	0.7674	0.057*
H3A3	−0.3664	1.1013	0.8128	0.057*
O1B	0.11137 (13)	0.63217 (12)	0.90836 (9)	0.0265 (3)
C1B	0.00810 (18)	0.60066 (17)	0.91249 (12)	0.0217 (4)
H1B	−0.0778	0.6349	0.9603	0.026*
N1B	0.01013 (14)	0.52302 (14)	0.85492 (10)	0.0200 (3)
C2B	0.13819 (18)	0.46641 (18)	0.78025 (12)	0.0239 (4)
H2B1	0.2006	0.5172	0.7663	0.036*
H2B2	0.1135	0.4611	0.7248	0.036*
H2B3	0.1867	0.3828	0.7994	0.036*
C3B	−0.11161 (19)	0.4817 (2)	0.86905 (13)	0.0273 (4)
H3B1	−0.1880	0.5222	0.9238	0.041*
H3B2	−0.0842	0.3914	0.8785	0.041*
H3B3	−0.1442	0.5037	0.8144	0.041*
O1C	0.30439 (13)	0.68644 (13)	1.02127 (9)	0.0291 (3)
C1C	0.38507 (17)	0.64521 (18)	1.06896 (13)	0.0241 (4)
H1C	0.3637	0.5873	1.1170	0.029*
N1C	0.49802 (14)	0.67611 (14)	1.05763 (10)	0.0205 (3)
C2C	0.5378 (2)	0.7637 (2)	0.98421 (14)	0.0308 (5)
H2C1	0.5914	0.7193	0.9257	0.046*
H2C2	0.5963	0.8025	1.0005	0.046*
H2C3	0.4525	0.8280	0.9773	0.046*
C3C	0.59075 (18)	0.61935 (19)	1.11494 (12)	0.0262 (4)
H3C1	0.5490	0.5661	1.1627	0.039*
H3C2	0.6019	0.6846	1.1447	0.039*
H3C3	0.6834	0.5694	1.0758	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0191 (6)	0.0198 (8)	0.0146 (7)	−0.0030 (5)	−0.0051 (5)	−0.0011 (6)
N2	0.0185 (6)	0.0182 (8)	0.0182 (7)	−0.0057 (5)	−0.0047 (5)	−0.0011 (6)
C11	0.0187 (7)	0.0172 (9)	0.0181 (8)	−0.0073 (6)	−0.0061 (6)	0.0027 (7)
C12	0.0188 (7)	0.0182 (9)	0.0178 (8)	−0.0067 (6)	−0.0066 (6)	0.0020 (7)
S12	0.01603 (18)	0.0199 (2)	0.01394 (18)	−0.00264 (15)	−0.00430 (14)	−0.00096 (17)
O121	0.0298 (6)	0.0212 (7)	0.0161 (6)	−0.0011 (5)	−0.0074 (5)	0.0024 (5)
O122	0.0277 (6)	0.0284 (8)	0.0258 (6)	−0.0116 (5)	−0.0115 (5)	−0.0002 (6)
O123	0.0190 (6)	0.0381 (8)	0.0174 (6)	−0.0045 (5)	−0.0036 (5)	−0.0029 (6)
C13	0.0197 (7)	0.0196 (10)	0.0183 (8)	−0.0056 (6)	−0.0047 (6)	0.0005 (7)
C14	0.0188 (7)	0.0217 (10)	0.0224 (8)	−0.0060 (6)	−0.0095 (6)	0.0047 (7)
Cl14	0.0243 (2)	0.0331 (3)	0.0275 (2)	−0.00036 (17)	−0.01432 (17)	0.0020 (2)
C15	0.0252 (8)	0.0241 (10)	0.0168 (8)	−0.0112 (7)	−0.0094 (7)	0.0036 (7)
Cl15	0.0327 (2)	0.0339 (3)	0.0187 (2)	−0.00937 (18)	−0.01341 (17)	0.00112 (19)
C16	0.0210 (8)	0.0196 (9)	0.0174 (8)	−0.0044 (6)	−0.0053 (6)	−0.0024 (7)
C21	0.0198 (7)	0.0192 (9)	0.0161 (8)	−0.0062 (6)	−0.0049 (6)	−0.0011 (7)
C22	0.0214 (8)	0.0192 (10)	0.0192 (8)	−0.0035 (7)	−0.0067 (6)	−0.0001 (7)
O22	0.0266 (6)	0.0291 (8)	0.0182 (6)	0.0034 (5)	−0.0078 (5)	−0.0064 (6)
N23	0.0217 (7)	0.0202 (8)	0.0142 (7)	−0.0004 (6)	−0.0045 (5)	−0.0017 (6)
N24	0.0219 (7)	0.0221 (8)	0.0147 (7)	−0.0036 (6)	−0.0039 (5)	−0.0014 (6)
C25	0.0202 (8)	0.0187 (9)	0.0187 (8)	−0.0059 (6)	−0.0049 (6)	−0.0012 (7)
C26	0.0257 (8)	0.0316 (11)	0.0160 (8)	−0.0029 (7)	−0.0062 (7)	−0.0026 (8)
C31	0.0205 (7)	0.0165 (9)	0.0182 (8)	−0.0060 (6)	−0.0068 (6)	0.0011 (7)
C32	0.0159 (7)	0.0166 (9)	0.0177 (8)	−0.0031 (6)	−0.0032 (6)	−0.0015 (7)
S33	0.01674 (18)	0.0165 (2)	0.01384 (18)	−0.00568 (15)	−0.00393 (14)	0.00031 (16)
C33	0.0186 (7)	0.0144 (9)	0.0154 (7)	−0.0065 (6)	−0.0037 (6)	−0.0005 (7)
O331	0.0302 (6)	0.0219 (7)	0.0209 (6)	−0.0127 (5)	−0.0075 (5)	−0.0010 (5)
O332	0.0184 (5)	0.0266 (7)	0.0157 (6)	−0.0046 (5)	−0.0033 (4)	0.0010 (5)
O333	0.0234 (6)	0.0162 (7)	0.0198 (6)	−0.0062 (5)	−0.0091 (5)	0.0023 (5)
C34	0.0191 (7)	0.0202 (10)	0.0222 (8)	−0.0059 (6)	−0.0086 (6)	0.0005 (7)
C35	0.0163 (7)	0.0231 (10)	0.0205 (8)	−0.0049 (6)	−0.0018 (6)	−0.0019 (7)
C36	0.0219 (8)	0.0202 (10)	0.0162 (8)	−0.0074 (7)	−0.0029 (6)	−0.0008 (7)
Ca1	0.01397 (14)	0.01639 (17)	0.01433 (15)	−0.00429 (12)	−0.00498 (12)	0.00012 (13)
O1A	0.0282 (6)	0.0283 (8)	0.0307 (7)	−0.0063 (5)	−0.0189 (5)	0.0024 (6)
C1A	0.0318 (9)	0.0269 (11)	0.0210 (9)	−0.0077 (8)	−0.0115 (7)	−0.0003 (8)
N1A	0.0215 (7)	0.0249 (9)	0.0267 (8)	−0.0065 (6)	−0.0119 (6)	0.0018 (7)
C2A	0.0367 (10)	0.0441 (14)	0.0372 (11)	−0.0189 (9)	−0.0200 (9)	0.0186 (10)
C3A	0.0224 (9)	0.0410 (13)	0.0481 (13)	−0.0052 (8)	−0.0125 (9)	−0.0015 (11)
O1B	0.0279 (6)	0.0230 (7)	0.0329 (7)	−0.0095 (5)	−0.0127 (5)	−0.0033 (6)
C1B	0.0241 (8)	0.0200 (10)	0.0217 (8)	−0.0068 (7)	−0.0087 (7)	0.0006 (7)
N1B	0.0243 (7)	0.0194 (8)	0.0189 (7)	−0.0093 (6)	−0.0077 (6)	0.0002 (6)
C2B	0.0244 (8)	0.0229 (10)	0.0245 (9)	−0.0061 (7)	−0.0083 (7)	−0.0028 (8)
C3B	0.0308 (9)	0.0359 (12)	0.0215 (9)	−0.0204 (8)	−0.0052 (7)	−0.0029 (8)
O1C	0.0265 (6)	0.0357 (8)	0.0318 (7)	−0.0141 (6)	−0.0185 (6)	0.0134 (6)
C1C	0.0237 (8)	0.0253 (10)	0.0247 (9)	−0.0090 (7)	−0.0109 (7)	0.0078 (8)
N1C	0.0218 (7)	0.0231 (9)	0.0187 (7)	−0.0078 (6)	−0.0101 (6)	0.0047 (6)
C2C	0.0314 (9)	0.0407 (13)	0.0287 (10)	−0.0203 (8)	−0.0162 (8)	0.0142 (9)
C3C	0.0236 (8)	0.0350 (12)	0.0219 (9)	−0.0081 (7)	−0.0128 (7)	0.0049 (8)

Geometric parameters (Å, º)

N1—N2	1.318 (2)	C34—H34	0.9500
N1—C11	1.4077 (19)	C35—C36	1.395 (2)
N1—H1	0.87 (2)	C35—H35	0.9500
N2—C21	1.309 (2)	C36—H36	0.9500
C11—C16	1.400 (2)	Ca1—O1C	2.2728 (11)
C11—C12	1.402 (2)	Ca1—O1B	2.2916 (14)
C12—C13	1.396 (2)	Ca1—O333^iii	2.3274 (13)
C12—S12	1.7878 (17)	Ca1—O332^i	2.3684 (12)
S12—O122	1.4386 (14)	Ca1—O1A	2.3715 (11)
S12—O121	1.4540 (12)	O1A—C1A	1.237 (2)
S12—O123	1.4590 (12)	C1A—N1A	1.326 (2)
O123—Ca1	2.2968 (13)	C1A—H1A	0.9500
C13—C14	1.392 (2)	N1A—C2A	1.445 (2)
C13—H13	0.9500	N1A—C3A	1.460 (2)
C14—C15	1.378 (3)	C2A—H2A1	0.9800
C14—Cl14	1.7356 (16)	C2A—H2A2	0.9800
C15—C16	1.387 (2)	C2A—H2A3	0.9800
C15—Cl15	1.7322 (17)	C3A—H3A1	0.9800
C16—H16	0.9500	C3A—H3A2	0.9800
C21—C25	1.445 (2)	C3A—H3A3	0.9800
C21—C22	1.473 (2)	O1B—C1B	1.245 (2)
C22—O22	1.224 (2)	C1B—N1B	1.317 (2)
C22—N23	1.374 (2)	C1B—H1B	0.9500
N23—N24	1.418 (2)	N1B—C2B	1.456 (2)
N23—C31	1.4231 (19)	N1B—C3B	1.464 (2)
N24—C25	1.306 (2)	C2B—H2B1	0.9800
C25—C26	1.486 (2)	C2B—H2B2	0.9800
C26—H26A	0.9800	C2B—H2B3	0.9800
C26—H26B	0.9800	C3B—H3B1	0.9800
C26—H26C	0.9800	C3B—H3B2	0.9800
C31—C36	1.394 (2)	C3B—H3B3	0.9800
C31—C32	1.396 (2)	O1C—C1C	1.2397 (19)
C32—C33	1.396 (2)	C1C—N1C	1.313 (2)
C32—H32	0.9500	C1C—H1C	0.9500
S33—O331	1.4489 (13)	N1C—C2C	1.463 (2)
S33—O332	1.4595 (11)	N1C—C3C	1.4657 (19)
S33—O333	1.4671 (12)	C2C—H2C1	0.9800
S33—C33	1.7742 (17)	C2C—H2C2	0.9800
C33—C34	1.386 (2)	C2C—H2C3	0.9800
O332—Ca1^i	2.3684 (12)	C3C—H3C1	0.9800
O333—Ca1^ii	2.3275 (13)	C3C—H3C2	0.9800
C34—C35	1.385 (2)	C3C—H3C3	0.9800
N2—N1—C11	118.42 (13)	C35—C36—H36	120.3
N2—N1—H1	123.8 (13)	O1C—Ca1—O1B	93.33 (5)
C11—N1—H1	117.1 (13)	O1C—Ca1—O123	88.71 (5)
C21—N2—N1	118.43 (14)	O1B—Ca1—O123	90.27 (5)
C16—C11—C12	119.62 (14)	O1C—Ca1—O333^iii	95.71 (5)
C16—C11—N1	119.18 (16)	O1B—Ca1—O333^iii	170.90 (4)
C12—C11—N1	121.17 (14)	O123—Ca1—O333^iii	90.98 (5)
C13—C12—C11	119.51 (15)	O1C—Ca1—O332^i	83.25 (4)
C13—C12—S12	117.17 (13)	O1B—Ca1—O332^i	90.02 (5)
C11—C12—S12	123.30 (11)	O123—Ca1—O332^i	171.96 (4)
O122—S12—O121	114.08 (8)	O333^iii—Ca1—O332^i	90.01 (5)
O122—S12—O123	113.23 (8)	O1C—Ca1—O1A	175.38 (5)
O121—S12—O123	112.72 (8)	O1B—Ca1—O1A	82.47 (5)
O122—S12—C12	106.62 (8)	O123—Ca1—O1A	93.22 (4)
O121—S12—C12	105.49 (8)	O333^iii—Ca1—O1A	88.47 (4)
O123—S12—C12	103.60 (7)	O332^i—Ca1—O1A	94.79 (4)
S12—O123—Ca1	164.83 (8)	C1A—O1A—Ca1	130.29 (12)
C14—C13—C12	120.39 (16)	O1A—C1A—N1A	125.42 (17)
C14—C13—H13	119.8	O1A—C1A—H1A	117.3
C12—C13—H13	119.8	N1A—C1A—H1A	117.3
C15—C14—C13	119.80 (14)	C1A—N1A—C2A	122.01 (15)
C15—C14—Cl14	121.35 (13)	C1A—N1A—C3A	121.24 (16)
C13—C14—Cl14	118.84 (14)	C2A—N1A—C3A	116.72 (14)
C14—C15—C16	120.86 (15)	N1A—C2A—H2A1	109.5
C14—C15—Cl15	121.14 (12)	N1A—C2A—H2A2	109.5
C16—C15—Cl15	118.00 (14)	H2A1—C2A—H2A2	109.5
C15—C16—C11	119.81 (17)	N1A—C2A—H2A3	109.5
C15—C16—H16	120.1	H2A1—C2A—H2A3	109.5
C11—C16—H16	120.1	H2A2—C2A—H2A3	109.5
N2—C21—C25	125.22 (15)	N1A—C3A—H3A1	109.5
N2—C21—C22	128.72 (16)	N1A—C3A—H3A2	109.5
C25—C21—C22	106.06 (13)	H3A1—C3A—H3A2	109.5
O22—C22—N23	128.53 (14)	N1A—C3A—H3A3	109.5
O22—C22—C21	128.18 (15)	H3A1—C3A—H3A3	109.5
N23—C22—C21	103.30 (14)	H3A2—C3A—H3A3	109.5
C22—N23—N24	112.82 (12)	C1B—O1B—Ca1	143.71 (13)
C22—N23—C31	128.64 (15)	O1B—C1B—N1B	124.31 (17)
N24—N23—C31	118.37 (13)	O1B—C1B—H1B	117.8
C25—N24—N23	106.93 (13)	N1B—C1B—H1B	117.8
N24—C25—C21	110.90 (14)	C1B—N1B—C2B	120.94 (15)
N24—C25—C26	122.47 (16)	C1B—N1B—C3B	121.19 (15)
C21—C25—C26	126.63 (14)	C2B—N1B—C3B	117.62 (16)
C25—C26—H26A	109.5	N1B—C2B—H2B1	109.5
C25—C26—H26B	109.5	N1B—C2B—H2B2	109.5
H26A—C26—H26B	109.5	H2B1—C2B—H2B2	109.5
C25—C26—H26C	109.5	N1B—C2B—H2B3	109.5
H26A—C26—H26C	109.5	H2B1—C2B—H2B3	109.5
H26B—C26—H26C	109.5	H2B2—C2B—H2B3	109.5
C36—C31—C32	120.94 (14)	N1B—C3B—H3B1	109.5
C36—C31—N23	118.78 (15)	N1B—C3B—H3B2	109.5
C32—C31—N23	120.27 (14)	H3B1—C3B—H3B2	109.5
C31—C32—C33	118.16 (14)	N1B—C3B—H3B3	109.5
C31—C32—H32	120.9	H3B1—C3B—H3B3	109.5
C33—C32—H32	120.9	H3B2—C3B—H3B3	109.5
O331—S33—O332	113.05 (8)	C1C—O1C—Ca1	167.47 (13)
O331—S33—O333	111.89 (7)	O1C—C1C—N1C	124.49 (16)
O332—S33—O333	112.13 (7)	O1C—C1C—H1C	117.8
O331—S33—C33	106.57 (8)	N1C—C1C—H1C	117.8
O332—S33—C33	107.02 (7)	C1C—N1C—C2C	120.53 (13)
O333—S33—C33	105.60 (8)	C1C—N1C—C3C	120.95 (14)
C34—C33—C32	121.70 (15)	C2C—N1C—C3C	118.45 (14)
C34—C33—S33	117.35 (12)	N1C—C2C—H2C1	109.5
C32—C33—S33	120.90 (12)	N1C—C2C—H2C2	109.5
S33—O332—Ca1^i	136.63 (7)	H2C1—C2C—H2C2	109.5
S33—O333—Ca1^ii	135.71 (7)	N1C—C2C—H2C3	109.5
C33—C34—C35	119.21 (14)	H2C1—C2C—H2C3	109.5
C33—C34—H34	120.4	H2C2—C2C—H2C3	109.5
C35—C34—H34	120.4	N1C—C3C—H3C1	109.5
C34—C35—C36	120.63 (15)	N1C—C3C—H3C2	109.5
C34—C35—H35	119.7	H3C1—C3C—H3C2	109.5
C36—C35—H35	119.7	N1C—C3C—H3C3	109.5
C31—C36—C35	119.35 (15)	H3C1—C3C—H3C3	109.5
C31—C36—H36	120.3	H3C2—C3C—H3C3	109.5
C11—N1—N2—C21	−174.52 (15)	N23—C31—C32—C33	179.67 (16)
N2—N1—C11—C16	5.6 (2)	C31—C32—C33—C34	−0.3 (3)
N2—N1—C11—C12	−176.30 (16)	C31—C32—C33—S33	176.99 (14)
C16—C11—C12—C13	−0.8 (3)	O331—S33—C33—C34	71.87 (15)
N1—C11—C12—C13	−178.90 (16)	O332—S33—C33—C34	−166.91 (13)
C16—C11—C12—S12	−179.07 (13)	O333—S33—C33—C34	−47.28 (15)
N1—C11—C12—S12	2.8 (2)	O331—S33—C33—C32	−105.56 (15)
C13—C12—S12—O122	−89.96 (14)	O332—S33—C33—C32	15.65 (17)
C11—C12—S12—O122	88.34 (16)	O333—S33—C33—C32	135.29 (14)
C13—C12—S12—O121	148.40 (13)	O331—S33—O332—Ca1^i	−57.17 (13)
C11—C12—S12—O121	−33.30 (17)	O333—S33—O332—Ca1^i	70.45 (13)
C13—C12—S12—O123	29.75 (16)	C33—S33—O332—Ca1^i	−174.20 (10)
C11—C12—S12—O123	−151.95 (15)	O331—S33—O333—Ca1^ii	174.22 (9)
O122—S12—O123—Ca1	−55.6 (4)	O332—S33—O333—Ca1^ii	45.98 (12)
O121—S12—O123—Ca1	75.8 (4)	C33—S33—O333—Ca1^ii	−70.22 (11)
C12—S12—O123—Ca1	−170.6 (3)	C32—C33—C34—C35	0.5 (3)
C11—C12—C13—C14	−0.2 (3)	S33—C33—C34—C35	−176.88 (15)
S12—C12—C13—C14	178.13 (14)	C33—C34—C35—C36	−0.1 (3)
C12—C13—C14—C15	0.7 (3)	C32—C31—C36—C35	0.6 (3)
C12—C13—C14—Cl14	−178.42 (13)	N23—C31—C36—C35	−179.29 (16)
C13—C14—C15—C16	−0.2 (3)	C34—C35—C36—C31	−0.4 (3)
Cl14—C14—C15—C16	178.95 (14)	S12—O123—Ca1—O1C	−35.4 (3)
C13—C14—C15—Cl15	178.85 (14)	S12—O123—Ca1—O1B	−128.7 (3)
Cl14—C14—C15—Cl15	−2.0 (2)	S12—O123—Ca1—O333^iii	60.3 (3)
C14—C15—C16—C11	−0.9 (3)	S12—O123—Ca1—O332^i	−36.7 (6)
Cl15—C15—C16—C11	−179.93 (14)	S12—O123—Ca1—O1A	148.8 (3)
C12—C11—C16—C15	1.4 (3)	O1C—Ca1—O1A—C1A	39.8 (8)
N1—C11—C16—C15	179.49 (16)	O1B—Ca1—O1A—C1A	64.51 (17)
N1—N2—C21—C25	−179.67 (17)	O123—Ca1—O1A—C1A	154.35 (17)
N1—N2—C21—C22	0.3 (3)	O333^iii—Ca1—O1A—C1A	−114.76 (17)
N2—C21—C22—O22	−0.2 (3)	O332^i—Ca1—O1A—C1A	−24.87 (17)
C25—C21—C22—O22	179.71 (19)	Ca1—O1A—C1A—N1A	176.04 (14)
N2—C21—C22—N23	179.93 (18)	O1A—C1A—N1A—C2A	0.8 (3)
C25—C21—C22—N23	−0.14 (19)	O1A—C1A—N1A—C3A	178.8 (2)
O22—C22—N23—N24	−179.80 (18)	O1C—Ca1—O1B—C1B	129.4 (2)
C21—C22—N23—N24	0.1 (2)	O123—Ca1—O1B—C1B	−141.9 (2)
O22—C22—N23—C31	−4.6 (3)	O333^iii—Ca1—O1B—C1B	−44.0 (4)
C21—C22—N23—C31	175.22 (16)	O332^i—Ca1—O1B—C1B	46.2 (2)
C22—N23—N24—C25	0.1 (2)	O1A—Ca1—O1B—C1B	−48.6 (2)
C31—N23—N24—C25	−175.65 (15)	Ca1—O1B—C1B—N1B	142.19 (16)
N23—N24—C25—C21	−0.2 (2)	O1B—C1B—N1B—C2B	0.3 (3)
N23—N24—C25—C26	−179.22 (17)	O1B—C1B—N1B—C3B	174.43 (16)
N2—C21—C25—N24	−179.88 (17)	O1B—Ca1—O1C—C1C	163.6 (6)
C22—C21—C25—N24	0.2 (2)	O123—Ca1—O1C—C1C	73.4 (6)
N2—C21—C25—C26	−0.9 (3)	O333^iii—Ca1—O1C—C1C	−17.4 (6)
C22—C21—C25—C26	179.20 (18)	O332^i—Ca1—O1C—C1C	−106.7 (6)
C22—N23—C31—C36	−158.26 (18)	O1A—Ca1—O1C—C1C	−171.8 (6)
N24—N23—C31—C36	16.7 (2)	Ca1—O1C—C1C—N1C	−20.5 (8)
C22—N23—C31—C32	21.8 (3)	O1C—C1C—N1C—C2C	−0.7 (3)
N24—N23—C31—C32	−163.26 (17)	O1C—C1C—N1C—C3C	−177.70 (19)
C36—C31—C32—C33	−0.3 (3)

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x+1, y−1, z; (iii) x−1, y+1, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O121	0.87 (2)	2.04 (2)	2.7556 (19)	138.5 (17)
N1—H1···O22	0.87 (2)	2.216 (19)	2.8384 (17)	128.3 (17)

(PY1834DMAc)

Crystal data

C32H46CaCl2N8O11S2	F(000) = 1872
Mr = 893.87	Dx = 1.430 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.9032 (9) Å	Cell parameters from 13733 reflections
b = 26.283 (4) Å	θ = 2.2–26.1°
c = 17.7857 (18) Å	µ = 0.45 mm^−1
β = 93.887 (8)°	T = 100 K
V = 4152.3 (9) Å^3	Plate, red
Z = 4	0.46 × 0.20 × 0.05 mm

Data collection

STOE IPDS II two-circle- diffractometer	7640 independent reflections
Radiation source: fine-focus sealed tube	4542 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.078
ω scans	θmax = 26.1°, θmin = 2.3°
Absorption correction: multi-scan MULABS (Spek, 1990; Blessing, 1995)	h = −11→10
Tmin = 0.821, Tmax = 0.978	k = −32→32
23644 measured reflections	l = −21→21

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)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.211	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.1149P)^2] where P = (Fo^2 + 2Fc^2)/3
7640 reflections	(Δ/σ)max < 0.001
522 parameters	Δρmax = 1.31 e Å^−3
0 restraints	Δρmin = −0.67 e Å^−3

Special details

Experimental.

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
N1	0.1162 (6)	0.56870 (18)	1.0093 (3)	0.0292 (11)
H1	0.128 (8)	0.577 (3)	0.965 (4)	0.038 (19)*
N2	0.1837 (5)	0.52859 (17)	1.0391 (3)	0.0289 (11)
C11	0.0352 (6)	0.6002 (2)	1.0565 (3)	0.0264 (12)
C12	−0.0247 (7)	0.6468 (2)	1.0314 (4)	0.0305 (13)
S12	0.01178 (17)	0.67273 (5)	0.94121 (9)	0.0307 (4)
O121	0.0078 (6)	0.62927 (17)	0.8906 (3)	0.0465 (12)
O122	0.1604 (5)	0.69446 (19)	0.9533 (3)	0.0444 (12)
O123	−0.1066 (5)	0.70939 (17)	0.9233 (3)	0.0405 (11)
C13	−0.1045 (7)	0.6763 (2)	1.0801 (3)	0.0306 (13)
H13	−0.1504	0.7071	1.0624	0.037*
C14	−0.1176 (7)	0.6614 (2)	1.1537 (4)	0.0323 (14)
Cl14	−0.21028 (19)	0.70085 (6)	1.21442 (10)	0.0425 (4)
C15	−0.0541 (6)	0.6161 (2)	1.1796 (3)	0.0274 (13)
Cl15	−0.06420 (18)	0.59616 (6)	1.27138 (8)	0.0369 (4)
C16	0.0204 (7)	0.5851 (2)	1.1311 (3)	0.0290 (13)
H16	0.0615	0.5535	1.1485	0.035*
C21	0.2605 (7)	0.4990 (2)	0.9966 (3)	0.0259 (12)
C22	0.2850 (7)	0.5037 (2)	0.9153 (3)	0.0273 (12)
O22	0.2345 (5)	0.53597 (15)	0.8712 (2)	0.0332 (10)
N23	0.3812 (5)	0.46359 (17)	0.9029 (3)	0.0268 (11)
N24	0.4172 (6)	0.43484 (17)	0.9697 (3)	0.0281 (11)
C25	0.3455 (7)	0.4554 (2)	1.0234 (3)	0.0280 (13)
C26	0.3568 (8)	0.4353 (2)	1.1026 (3)	0.0341 (14)
H26A	0.2635	0.4175	1.1125	0.051*
H26B	0.3726	0.4636	1.1381	0.051*
H26C	0.4418	0.4116	1.1089	0.051*
C31	0.4386 (6)	0.4473 (2)	0.8345 (3)	0.0254 (12)
C32	0.3829 (6)	0.4674 (2)	0.7662 (3)	0.0278 (13)
H32	0.3072	0.4930	0.7647	0.033*
C33	0.4391 (6)	0.4498 (2)	0.6995 (3)	0.0268 (12)
S33	0.35905 (16)	0.47412 (5)	0.61260 (8)	0.0260 (3)
O331	0.3992 (5)	0.43765 (18)	0.5556 (2)	0.0410 (11)
O332	0.1996 (4)	0.47783 (18)	0.6195 (2)	0.0356 (10)
O333	0.4311 (5)	0.52335 (18)	0.6019 (3)	0.0449 (12)
C34	0.5524 (7)	0.4136 (2)	0.7006 (3)	0.0292 (13)
H34	0.5908	0.4022	0.6550	0.035*
C35	0.6086 (7)	0.3943 (2)	0.7695 (4)	0.0331 (14)
H35	0.6863	0.3695	0.7709	0.040*
C36	0.5527 (7)	0.4109 (2)	0.8369 (3)	0.0298 (13)
H36	0.5921	0.3975	0.8838	0.036*
Ca1	0.52893 (12)	0.40127 (4)	0.46153 (6)	0.0248 (3)
O1A	0.7410 (4)	0.40046 (16)	0.5425 (2)	0.0319 (9)
C1A	0.8765 (10)	0.3897 (4)	0.5317 (5)	0.064 (2)
N1A	0.9478 (8)	0.3530 (3)	0.5567 (5)	0.070 (2)
C2A	0.8536 (9)	0.3175 (2)	0.6060 (4)	0.0404 (16)
H2A1	0.7571	0.3338	0.6144	0.061*
H2A2	0.9093	0.3115	0.6546	0.061*
H2A3	0.8353	0.2850	0.5800	0.061*
C3A	1.1054 (8)	0.3394 (3)	0.5458 (5)	0.0486 (18)
H3A1	1.1249	0.3434	0.4925	0.073*
H3A2	1.1233	0.3039	0.5609	0.073*
H3A3	1.1729	0.3617	0.5766	0.073*
C4A	0.9699 (7)	0.4247 (2)	0.4797 (4)	0.0345 (14)
H4A1	1.0685	0.4320	0.5053	0.052*
H4A2	0.9155	0.4566	0.4695	0.052*
H4A3	0.9838	0.4071	0.4321	0.052*
O1B	0.3219 (5)	0.39733 (18)	0.3806 (3)	0.0416 (11)
C1B	0.2196 (12)	0.4008 (3)	0.3248 (6)	0.071 (3)
N1B	0.1543 (8)	0.4414 (3)	0.3137 (4)	0.065 (2)
C2B	0.1909 (8)	0.4878 (2)	0.3621 (4)	0.0416 (17)
H2B1	0.2656	0.4787	0.4029	0.062*
H2B2	0.0991	0.5000	0.3836	0.062*
H2B3	0.2316	0.5146	0.3311	0.062*
C3B	0.0292 (8)	0.4485 (3)	0.2523 (4)	0.0451 (17)
H3B1	0.0174	0.4173	0.2224	0.068*
H3B2	0.0545	0.4768	0.2196	0.068*
H3B3	−0.0652	0.4561	0.2754	0.068*
C4B	0.1817 (8)	0.3559 (3)	0.2747 (4)	0.0440 (17)
H4B1	0.0724	0.3511	0.2701	0.066*
H4B2	0.2301	0.3254	0.2966	0.066*
H4B3	0.2180	0.3621	0.2247	0.066*
O1C	0.4737 (5)	0.32100 (17)	0.5065 (3)	0.0497 (13)
C1C	0.4650 (9)	0.2787 (3)	0.5313 (8)	0.082 (4)
N1C	0.4770 (7)	0.2366 (3)	0.5112 (6)	0.074 (2)
C2C	0.5251 (11)	0.2360 (4)	0.4305 (5)	0.069 (3)
H2C1	0.5048	0.2693	0.4071	0.103*
H2C2	0.4684	0.2097	0.4016	0.103*
H2C3	0.6330	0.2286	0.4308	0.103*
C3C	0.4663 (8)	0.1870 (2)	0.5485 (5)	0.052 (2)
H3C1	0.5667	0.1761	0.5681	0.077*
H3C2	0.4249	0.1618	0.5120	0.077*
H3C3	0.4001	0.1898	0.5901	0.077*
C4C	0.4236 (9)	0.2769 (3)	0.6247 (5)	0.0527 (19)
H4C1	0.3317	0.2571	0.6296	0.079*
H4C2	0.4086	0.3117	0.6428	0.079*
H4C3	0.5073	0.2611	0.6548	0.079*
O1D	0.6887 (5)	0.36110 (19)	0.3818 (3)	0.0447 (12)
C1D	0.7091 (7)	0.3458 (2)	0.3168 (3)	0.0311 (13)
N1D	0.8013 (6)	0.30623 (19)	0.3084 (3)	0.0346 (12)
C2D	0.8762 (8)	0.2805 (3)	0.3708 (5)	0.051 (2)
H2D1	0.8426	0.2946	0.4179	0.076*
H2D2	0.9852	0.2852	0.3695	0.076*
H2D3	0.8523	0.2442	0.3680	0.076*
C3D	0.8224 (8)	0.2819 (3)	0.2351 (4)	0.055 (2)
H3D1	0.7617	0.2509	0.2304	0.083*
H3D2	0.9288	0.2734	0.2318	0.083*
H3D3	0.7905	0.3055	0.1943	0.083*
C4D	0.6313 (9)	0.3707 (3)	0.2491 (4)	0.0506 (19)
H4D1	0.5646	0.3976	0.2654	0.076*
H4D2	0.5719	0.3453	0.2197	0.076*
H4D3	0.7066	0.3855	0.2178	0.076*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.037 (3)	0.030 (3)	0.022 (3)	0.001 (2)	0.010 (2)	0.003 (2)
N2	0.028 (3)	0.030 (2)	0.030 (3)	−0.0002 (19)	0.009 (2)	0.002 (2)
C11	0.026 (3)	0.032 (3)	0.022 (3)	−0.005 (2)	0.004 (3)	−0.004 (2)
C12	0.026 (3)	0.028 (3)	0.037 (4)	−0.001 (2)	0.003 (3)	−0.001 (2)
S12	0.0290 (8)	0.0331 (7)	0.0302 (8)	0.0034 (6)	0.0048 (7)	0.0023 (6)
O121	0.069 (3)	0.039 (2)	0.031 (2)	0.011 (2)	0.002 (3)	0.0026 (19)
O122	0.030 (2)	0.060 (3)	0.043 (3)	−0.006 (2)	0.004 (2)	0.014 (2)
O123	0.035 (2)	0.047 (3)	0.039 (3)	0.0111 (19)	0.003 (2)	0.008 (2)
C13	0.026 (3)	0.032 (3)	0.034 (3)	−0.002 (2)	0.003 (3)	−0.001 (2)
C14	0.024 (3)	0.036 (3)	0.038 (4)	−0.003 (2)	0.008 (3)	−0.011 (3)
Cl14	0.0388 (9)	0.0498 (9)	0.0403 (9)	0.0076 (7)	0.0131 (8)	−0.0096 (7)
C15	0.026 (3)	0.039 (3)	0.018 (3)	−0.007 (2)	0.006 (3)	−0.004 (2)
Cl15	0.0384 (8)	0.0458 (8)	0.0281 (8)	−0.0032 (7)	0.0134 (7)	−0.0006 (6)
C16	0.030 (3)	0.032 (3)	0.025 (3)	0.000 (2)	0.007 (3)	0.001 (2)
C21	0.031 (3)	0.032 (3)	0.016 (3)	−0.003 (2)	0.007 (2)	−0.001 (2)
C22	0.028 (3)	0.033 (3)	0.021 (3)	0.001 (2)	0.006 (3)	0.001 (2)
O22	0.039 (2)	0.035 (2)	0.026 (2)	0.0117 (18)	0.008 (2)	0.0067 (17)
N23	0.030 (3)	0.032 (2)	0.019 (2)	0.0016 (19)	0.005 (2)	0.0034 (18)
N24	0.033 (3)	0.032 (2)	0.019 (2)	0.001 (2)	0.003 (2)	0.0043 (19)
C25	0.033 (3)	0.033 (3)	0.018 (3)	−0.002 (2)	0.004 (3)	0.000 (2)
C26	0.046 (4)	0.036 (3)	0.021 (3)	0.004 (3)	0.005 (3)	0.001 (2)
C31	0.028 (3)	0.029 (3)	0.020 (3)	−0.003 (2)	0.004 (3)	0.000 (2)
C32	0.026 (3)	0.033 (3)	0.026 (3)	0.000 (2)	0.010 (3)	0.002 (2)
C33	0.026 (3)	0.030 (3)	0.024 (3)	−0.004 (2)	0.002 (3)	−0.001 (2)
S33	0.0218 (7)	0.0378 (8)	0.0190 (7)	0.0009 (5)	0.0055 (6)	0.0037 (5)
O331	0.040 (3)	0.062 (3)	0.022 (2)	0.014 (2)	0.008 (2)	−0.0048 (19)
O332	0.016 (2)	0.065 (3)	0.026 (2)	0.0059 (18)	0.0006 (19)	0.0103 (19)
O333	0.040 (3)	0.051 (3)	0.042 (3)	−0.011 (2)	−0.009 (2)	0.019 (2)
C34	0.030 (3)	0.034 (3)	0.025 (3)	0.001 (2)	0.010 (3)	0.000 (2)
C35	0.029 (3)	0.039 (3)	0.032 (3)	0.009 (2)	0.003 (3)	0.000 (3)
C36	0.030 (3)	0.034 (3)	0.025 (3)	0.004 (2)	0.001 (3)	0.002 (2)
Ca1	0.0227 (6)	0.0284 (6)	0.0233 (6)	0.0032 (4)	0.0021 (5)	−0.0020 (4)
O1A	0.022 (2)	0.051 (2)	0.022 (2)	0.0080 (18)	0.0024 (18)	−0.0060 (18)
C1A	0.051 (5)	0.092 (7)	0.046 (5)	0.022 (5)	−0.029 (4)	−0.035 (4)
N1A	0.050 (4)	0.081 (5)	0.077 (5)	0.020 (4)	−0.010 (4)	−0.035 (4)
C2A	0.057 (4)	0.035 (3)	0.030 (3)	−0.007 (3)	0.007 (3)	0.005 (3)
C3A	0.030 (3)	0.050 (4)	0.066 (5)	0.008 (3)	0.004 (4)	−0.008 (3)
C4A	0.023 (3)	0.048 (4)	0.032 (4)	−0.003 (3)	−0.004 (3)	0.007 (3)
O1B	0.027 (2)	0.052 (3)	0.042 (3)	0.001 (2)	−0.021 (2)	0.000 (2)
C1B	0.080 (7)	0.055 (5)	0.085 (7)	−0.013 (5)	0.057 (6)	−0.005 (5)
N1B	0.053 (4)	0.075 (5)	0.072 (5)	0.001 (4)	0.035 (4)	0.016 (4)
C2B	0.037 (4)	0.035 (3)	0.055 (4)	−0.002 (3)	0.011 (3)	−0.008 (3)
C3B	0.042 (4)	0.056 (4)	0.035 (4)	0.011 (3)	−0.017 (4)	0.002 (3)
C4B	0.043 (4)	0.041 (4)	0.048 (4)	−0.002 (3)	0.003 (4)	−0.007 (3)
O1C	0.039 (3)	0.032 (3)	0.077 (4)	−0.0032 (19)	−0.009 (3)	0.009 (2)
C1C	0.031 (4)	0.031 (4)	0.176 (13)	−0.007 (3)	−0.049 (6)	0.016 (5)
N1C	0.032 (3)	0.064 (5)	0.121 (8)	−0.009 (3)	−0.021 (4)	0.019 (4)
C2C	0.060 (5)	0.087 (6)	0.062 (6)	−0.021 (5)	0.025 (5)	−0.007 (5)
C3C	0.032 (3)	0.032 (3)	0.090 (6)	−0.002 (3)	−0.004 (4)	0.009 (3)
C4C	0.040 (4)	0.062 (5)	0.055 (5)	−0.002 (3)	−0.006 (4)	−0.011 (4)
O1D	0.036 (3)	0.062 (3)	0.036 (3)	0.016 (2)	0.006 (2)	−0.015 (2)
C1D	0.032 (3)	0.032 (3)	0.030 (3)	−0.002 (2)	0.008 (3)	−0.001 (2)
N1D	0.033 (3)	0.042 (3)	0.030 (3)	0.001 (2)	0.013 (3)	−0.007 (2)
C2D	0.036 (4)	0.058 (4)	0.060 (5)	0.014 (3)	0.014 (4)	0.014 (4)
C3D	0.040 (4)	0.078 (5)	0.048 (5)	−0.008 (4)	0.014 (4)	−0.037 (4)
C4D	0.049 (4)	0.060 (5)	0.042 (4)	−0.001 (3)	−0.001 (4)	0.013 (3)

Geometric parameters (Å, º)

N1—N2	1.307 (7)	N1A—C3A	1.474 (9)
N1—C11	1.412 (7)	N1A—C2A	1.563 (11)
N1—H1	0.83 (7)	C2A—H2A1	0.9800
N2—C21	1.310 (7)	C2A—H2A2	0.9800
C11—C12	1.395 (8)	C2A—H2A3	0.9800
C11—C16	1.400 (8)	C3A—H3A1	0.9800
C12—C13	1.394 (8)	C3A—H3A2	0.9800
C12—S12	1.793 (6)	C3A—H3A3	0.9800
S12—O122	1.444 (5)	C4A—H4A1	0.9800
S12—O123	1.447 (5)	C4A—H4A2	0.9800
S12—O121	1.453 (5)	C4A—H4A3	0.9800
C13—C14	1.379 (9)	O1B—C1B	1.304 (13)
C13—H13	0.9500	C1B—N1B	1.225 (11)
C14—C15	1.384 (9)	C1B—C4B	1.503 (11)
C14—Cl14	1.744 (5)	N1B—C2B	1.515 (11)
C15—C16	1.388 (8)	N1B—C3B	1.517 (11)
C15—Cl15	1.723 (6)	C2B—H2B1	0.9800
C16—H16	0.9500	C2B—H2B2	0.9800
C21—C25	1.435 (8)	C2B—H2B3	0.9800
C21—C22	1.481 (8)	C3B—H3B1	0.9800
C22—O22	1.220 (7)	C3B—H3B2	0.9800
C22—N23	1.386 (7)	C3B—H3B3	0.9800
N23—C31	1.417 (7)	C4B—H4B1	0.9800
N23—N24	1.426 (7)	C4B—H4B2	0.9800
N24—C25	1.302 (7)	C4B—H4B3	0.9800
C25—C26	1.503 (8)	O1C—C1C	1.199 (9)
C26—H26A	0.9800	C1C—N1C	1.170 (11)
C26—H26B	0.9800	C1C—C4C	1.728 (16)
C26—H26C	0.9800	N1C—C3C	1.470 (10)
C31—C32	1.386 (8)	N1C—C2C	1.526 (13)
C31—C36	1.394 (8)	C2C—H2C1	0.9800
C32—C33	1.396 (7)	C2C—H2C2	0.9800
C32—H32	0.9500	C2C—H2C3	0.9800
C33—C34	1.386 (8)	C3C—H3C1	0.9800
C33—S33	1.777 (6)	C3C—H3C2	0.9800
S33—O332	1.437 (4)	C3C—H3C3	0.9800
S33—O331	1.458 (4)	C4C—H4C1	0.9800
S33—O333	1.462 (5)	C4C—H4C2	0.9800
O331—Ca1	2.304 (4)	C4C—H4C3	0.9800
O333—Ca1^i	2.320 (4)	O1D—C1D	1.248 (7)
C34—C35	1.388 (9)	C1D—N1D	1.340 (8)
C34—H34	0.9500	C1D—C4D	1.499 (10)
C35—C36	1.398 (8)	N1D—C2D	1.427 (10)
C35—H35	0.9500	N1D—C3D	1.475 (8)
C36—H36	0.9500	C2D—H2D1	0.9800
Ca1—O1B	2.263 (5)	C2D—H2D2	0.9800
Ca1—O1A	2.295 (4)	C2D—H2D3	0.9800
Ca1—O333^i	2.320 (4)	C3D—H3D1	0.9800
Ca1—O1C	2.321 (5)	C3D—H3D2	0.9800
Ca1—O1D	2.328 (4)	C3D—H3D3	0.9800
O1A—C1A	1.266 (9)	C4D—H4D1	0.9800
C1A—N1A	1.221 (12)	C4D—H4D2	0.9800
C1A—C4A	1.580 (12)	C4D—H4D3	0.9800
N2—N1—C11	118.1 (5)	C3A—N1A—C2A	118.7 (7)
N2—N1—H1	121 (5)	N1A—C2A—H2A1	109.5
C11—N1—H1	120 (5)	N1A—C2A—H2A2	109.5
N1—N2—C21	119.3 (5)	H2A1—C2A—H2A2	109.5
C12—C11—C16	119.6 (5)	N1A—C2A—H2A3	109.5
C12—C11—N1	121.6 (5)	H2A1—C2A—H2A3	109.5
C16—C11—N1	118.8 (5)	H2A2—C2A—H2A3	109.5
C13—C12—C11	119.3 (6)	N1A—C3A—H3A1	109.5
C13—C12—S12	118.4 (4)	N1A—C3A—H3A2	109.5
C11—C12—S12	122.1 (4)	H3A1—C3A—H3A2	109.5
O122—S12—O123	114.6 (3)	N1A—C3A—H3A3	109.5
O122—S12—O121	112.8 (3)	H3A1—C3A—H3A3	109.5
O123—S12—O121	113.6 (3)	H3A2—C3A—H3A3	109.5
O122—S12—C12	103.7 (3)	C1A—C4A—H4A1	109.5
O123—S12—C12	106.1 (3)	C1A—C4A—H4A2	109.5
O121—S12—C12	104.9 (3)	H4A1—C4A—H4A2	109.5
C14—C13—C12	120.8 (6)	C1A—C4A—H4A3	109.5
C14—C13—H13	119.6	H4A1—C4A—H4A3	109.5
C12—C13—H13	119.6	H4A2—C4A—H4A3	109.5
C13—C14—C15	120.1 (5)	C1B—O1B—Ca1	167.9 (5)
C13—C14—Cl14	119.6 (5)	N1B—C1B—O1B	119.0 (9)
C15—C14—Cl14	120.3 (5)	N1B—C1B—C4B	120.2 (11)
C14—C15—C16	120.0 (5)	O1B—C1B—C4B	120.8 (8)
C14—C15—Cl15	122.0 (4)	C1B—N1B—C2B	121.8 (9)
C16—C15—Cl15	117.9 (5)	C1B—N1B—C3B	122.8 (9)
C15—C16—C11	120.1 (5)	C2B—N1B—C3B	115.4 (6)
C15—C16—H16	119.9	N1B—C2B—H2B1	109.5
C11—C16—H16	119.9	N1B—C2B—H2B2	109.5
N2—C21—C25	124.5 (5)	H2B1—C2B—H2B2	109.5
N2—C21—C22	129.1 (5)	N1B—C2B—H2B3	109.5
C25—C21—C22	106.4 (4)	H2B1—C2B—H2B3	109.5
O22—C22—N23	129.1 (5)	H2B2—C2B—H2B3	109.5
O22—C22—C21	127.8 (5)	N1B—C3B—H3B1	109.5
N23—C22—C21	103.1 (5)	N1B—C3B—H3B2	109.5
C22—N23—C31	129.1 (5)	H3B1—C3B—H3B2	109.5
C22—N23—N24	112.1 (4)	N1B—C3B—H3B3	109.5
C31—N23—N24	118.8 (4)	H3B1—C3B—H3B3	109.5
C25—N24—N23	107.3 (4)	H3B2—C3B—H3B3	109.5
N24—C25—C21	111.2 (5)	C1B—C4B—H4B1	109.5
N24—C25—C26	122.4 (5)	C1B—C4B—H4B2	109.5
C21—C25—C26	126.4 (5)	H4B1—C4B—H4B2	109.5
C25—C26—H26A	109.5	C1B—C4B—H4B3	109.5
C25—C26—H26B	109.5	H4B1—C4B—H4B3	109.5
H26A—C26—H26B	109.5	H4B2—C4B—H4B3	109.5
C25—C26—H26C	109.5	C1C—O1C—Ca1	171.5 (5)
H26A—C26—H26C	109.5	N1C—C1C—O1C	139.0 (14)
H26B—C26—H26C	109.5	N1C—C1C—C4C	107.3 (9)
C32—C31—C36	120.4 (5)	O1C—C1C—C4C	113.7 (9)
C32—C31—N23	120.6 (5)	C1C—N1C—C3C	133.8 (11)
C36—C31—N23	119.1 (5)	C1C—N1C—C2C	109.5 (9)
C31—C32—C33	119.4 (5)	C3C—N1C—C2C	116.5 (8)
C31—C32—H32	120.3	N1C—C2C—H2C1	109.5
C33—C32—H32	120.3	N1C—C2C—H2C2	109.5
C34—C33—C32	121.2 (6)	H2C1—C2C—H2C2	109.5
C34—C33—S33	120.5 (4)	N1C—C2C—H2C3	109.5
C32—C33—S33	118.3 (4)	H2C1—C2C—H2C3	109.5
O332—S33—O331	113.2 (3)	H2C2—C2C—H2C3	109.5
O332—S33—O333	113.3 (3)	N1C—C3C—H3C1	109.5
O331—S33—O333	111.2 (3)	N1C—C3C—H3C2	109.5
O332—S33—C33	106.9 (2)	H3C1—C3C—H3C2	109.5
O331—S33—C33	105.4 (3)	N1C—C3C—H3C3	109.5
O333—S33—C33	106.1 (3)	H3C1—C3C—H3C3	109.5
S33—O331—Ca1	159.5 (3)	H3C2—C3C—H3C3	109.5
S33—O333—Ca1^i	154.4 (3)	C1C—C4C—H4C1	109.5
C33—C34—C35	118.8 (5)	C1C—C4C—H4C2	109.5
C33—C34—H34	120.6	H4C1—C4C—H4C2	109.5
C35—C34—H34	120.6	C1C—C4C—H4C3	109.5
C34—C35—C36	121.0 (5)	H4C1—C4C—H4C3	109.5
C34—C35—H35	119.5	H4C2—C4C—H4C3	109.5
C36—C35—H35	119.5	C1D—O1D—Ca1	147.5 (5)
C31—C36—C35	119.3 (6)	O1D—C1D—N1D	118.9 (6)
C31—C36—H36	120.4	O1D—C1D—C4D	121.0 (6)
C35—C36—H36	120.4	N1D—C1D—C4D	120.1 (6)
O1B—Ca1—O1A	176.77 (17)	C1D—N1D—C2D	122.5 (5)
O1B—Ca1—O331	93.12 (18)	C1D—N1D—C3D	123.4 (6)
O1A—Ca1—O331	88.85 (16)	C2D—N1D—C3D	113.7 (6)
O1B—Ca1—O333^i	82.80 (18)	N1D—C2D—H2D1	109.5
O1A—Ca1—O333^i	99.56 (17)	N1D—C2D—H2D2	109.5
O331—Ca1—O333^i	95.74 (18)	H2D1—C2D—H2D2	109.5
O1B—Ca1—O1C	89.73 (19)	N1D—C2D—H2D3	109.5
O1A—Ca1—O1C	87.71 (18)	H2D1—C2D—H2D3	109.5
O331—Ca1—O1C	89.93 (18)	H2D2—C2D—H2D3	109.5
O333^i—Ca1—O1C	170.8 (2)	N1D—C3D—H3D1	109.5
O1B—Ca1—O1D	95.53 (18)	N1D—C3D—H3D2	109.5
O1A—Ca1—O1D	82.38 (16)	H3D1—C3D—H3D2	109.5
O331—Ca1—O1D	170.85 (18)	N1D—C3D—H3D3	109.5
O333^i—Ca1—O1D	88.31 (18)	H3D1—C3D—H3D3	109.5
O1C—Ca1—O1D	87.14 (19)	H3D2—C3D—H3D3	109.5
C1A—O1A—Ca1	131.2 (5)	C1D—C4D—H4D1	109.5
N1A—C1A—O1A	126.8 (10)	C1D—C4D—H4D2	109.5
N1A—C1A—C4A	113.0 (8)	H4D1—C4D—H4D2	109.5
O1A—C1A—C4A	120.2 (8)	C1D—C4D—H4D3	109.5
C1A—N1A—C3A	128.4 (9)	H4D1—C4D—H4D3	109.5
C1A—N1A—C2A	112.9 (7)	H4D2—C4D—H4D3	109.5
C11—N1—N2—C21	−179.5 (5)	C33—S33—O331—Ca1	−97.2 (9)
N2—N1—C11—C12	172.3 (6)	O332—S33—O333—Ca1^i	−61.6 (8)
N2—N1—C11—C16	−5.1 (8)	O331—S33—O333—Ca1^i	67.2 (8)
C16—C11—C12—C13	−3.0 (9)	C33—S33—O333—Ca1^i	−178.6 (7)
N1—C11—C12—C13	179.6 (5)	C32—C33—C34—C35	0.8 (9)
C16—C11—C12—S12	171.3 (5)	S33—C33—C34—C35	−177.9 (4)
N1—C11—C12—S12	−6.1 (8)	C33—C34—C35—C36	0.0 (9)
C13—C12—S12—O122	95.1 (5)	C32—C31—C36—C35	−1.0 (9)
C11—C12—S12—O122	−79.3 (6)	N23—C31—C36—C35	179.3 (5)
C13—C12—S12—O123	−26.0 (6)	C34—C35—C36—C31	0.1 (9)
C11—C12—S12—O123	159.7 (5)	S33—O331—Ca1—O1B	−123.8 (9)
C13—C12—S12—O121	−146.5 (5)	S33—O331—Ca1—O1A	58.8 (9)
C11—C12—S12—O121	39.2 (6)	S33—O331—Ca1—O333^i	−40.7 (9)
C11—C12—C13—C14	3.6 (9)	S33—O331—Ca1—O1C	146.5 (9)
S12—C12—C13—C14	−170.9 (5)	S33—O331—Ca1—O1D	75.3 (15)
C12—C13—C14—C15	−1.5 (9)	O1B—Ca1—O1A—C1A	60 (3)
C12—C13—C14—Cl14	176.8 (5)	O331—Ca1—O1A—C1A	−172.3 (7)
C13—C14—C15—C16	−1.3 (9)	O333^i—Ca1—O1A—C1A	−76.7 (8)
Cl14—C14—C15—C16	−179.5 (5)	O1C—Ca1—O1A—C1A	97.7 (8)
C13—C14—C15—Cl15	178.8 (5)	O1D—Ca1—O1A—C1A	10.3 (7)
Cl14—C14—C15—Cl15	0.6 (8)	Ca1—O1A—C1A—N1A	−112.1 (9)
C14—C15—C16—C11	1.8 (9)	Ca1—O1A—C1A—C4A	66.4 (9)
Cl15—C15—C16—C11	−178.3 (5)	O1A—C1A—N1A—C3A	−179.7 (7)
C12—C11—C16—C15	0.3 (9)	C4A—C1A—N1A—C3A	1.8 (13)
N1—C11—C16—C15	177.8 (5)	O1A—C1A—N1A—C2A	0.4 (13)
N1—N2—C21—C25	176.7 (6)	C4A—C1A—N1A—C2A	−178.2 (6)
N1—N2—C21—C22	0.0 (9)	O1A—Ca1—O1B—C1B	−110 (3)
N2—C21—C22—O22	−2.0 (11)	O331—Ca1—O1B—C1B	122 (2)
C25—C21—C22—O22	−179.2 (6)	O333^i—Ca1—O1B—C1B	27 (2)
N2—C21—C22—N23	176.6 (6)	O1C—Ca1—O1B—C1B	−148 (2)
C25—C21—C22—N23	−0.5 (6)	O1D—Ca1—O1B—C1B	−61 (2)
O22—C22—N23—C31	−4.7 (11)	Ca1—O1B—C1B—N1B	−73 (3)
C21—C22—N23—C31	176.7 (5)	Ca1—O1B—C1B—C4B	107 (2)
O22—C22—N23—N24	178.7 (6)	O1B—C1B—N1B—C2B	1.0 (10)
C21—C22—N23—N24	0.0 (6)	C4B—C1B—N1B—C2B	−179.0 (6)
C22—N23—N24—C25	0.5 (7)	O1B—C1B—N1B—C3B	−177.3 (6)
C31—N23—N24—C25	−176.5 (5)	C4B—C1B—N1B—C3B	2.6 (10)
N23—N24—C25—C21	−0.9 (7)	O1B—Ca1—O1C—C1C	148 (5)
N23—N24—C25—C26	−179.8 (5)	O1A—Ca1—O1C—C1C	−30 (5)
N2—C21—C25—N24	−176.4 (6)	O331—Ca1—O1C—C1C	−119 (5)
C22—C21—C25—N24	0.9 (7)	O333^i—Ca1—O1C—C1C	113 (5)
N2—C21—C25—C26	2.4 (10)	O1D—Ca1—O1C—C1C	53 (5)
C22—C21—C25—C26	179.7 (6)	Ca1—O1C—C1C—N1C	−80 (5)
C22—N23—C31—C32	−9.7 (9)	Ca1—O1C—C1C—C4C	100 (5)
N24—N23—C31—C32	166.8 (5)	O1C—C1C—N1C—C3C	178.4 (9)
C22—N23—C31—C36	169.9 (6)	C4C—C1C—N1C—C3C	−1.0 (11)
N24—N23—C31—C36	−13.6 (8)	O1C—C1C—N1C—C2C	3.6 (14)
C36—C31—C32—C33	1.9 (8)	C4C—C1C—N1C—C2C	−175.8 (6)
N23—C31—C32—C33	−178.5 (5)	O1B—Ca1—O1D—C1D	13.0 (8)
C31—C32—C33—C34	−1.8 (9)	O1A—Ca1—O1D—C1D	−169.5 (8)
C31—C32—C33—S33	177.0 (4)	O331—Ca1—O1D—C1D	173.9 (10)
C34—C33—S33—O332	138.8 (5)	O333^i—Ca1—O1D—C1D	−69.6 (8)
C32—C33—S33—O332	−40.0 (5)	O1C—Ca1—O1D—C1D	102.5 (8)
C34—C33—S33—O331	18.0 (5)	Ca1—O1D—C1D—N1D	−152.5 (6)
C32—C33—S33—O331	−160.7 (5)	Ca1—O1D—C1D—C4D	27.0 (11)
C34—C33—S33—O333	−100.0 (5)	O1D—C1D—N1D—C2D	0.6 (9)
C32—C33—S33—O333	81.2 (5)	C4D—C1D—N1D—C2D	−178.9 (6)
O332—S33—O331—Ca1	146.3 (8)	O1D—C1D—N1D—C3D	174.0 (6)
O333—S33—O331—Ca1	17.4 (10)	C4D—C1D—N1D—C3D	−5.6 (9)

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
N1—H1···O121	0.83 (7)	2.14 (7)	2.764 (7)	132 (6)
N1—H1···O22	0.83 (7)	2.26 (7)	2.868 (6)	131 (6)

(PY1914DMF)

Crystal data

C29H41CaClN8O11S2	Z = 2
Mr = 817.35	F(000) = 856
Triclinic, P1	Dx = 1.470 Mg m^−3
a = 8.1479 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.1042 (8) Å	Cell parameters from 37175 reflections
c = 18.1233 (12) Å	θ = 2.2–27.5°
α = 90.134 (5)°	µ = 0.42 mm^−1
β = 99.765 (5)°	T = 100 K
γ = 104.181 (5)°	Block, orange
V = 1847.0 (2) Å^3	0.43 × 0.41 × 0.37 mm

Data collection

STOE IPDS II two-circle- diffractometer	8457 independent reflections
Radiation source: fine-focus sealed tube	6914 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
ω scans	θmax = 27.6°, θmin = 2.3°
Absorption correction: multi-scan MULABS (Spek, 1990; Blessing, 1995)	h = −10→10
Tmin = 0.839, Tmax = 0.859	k = −17→16
37376 measured reflections	l = −23→23

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.077	H-atom parameters constrained
S = 0.97	w = 1/[σ^2(Fo^2) + (0.0525P)^2] where P = (Fo^2 + 2Fc^2)/3
8457 reflections	(Δ/σ)max = 0.001
482 parameters	Δρmax = 0.48 e Å^−3
0 restraints	Δρmin = −0.40 e Å^−3

Special details

Experimental.

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
N1	0.20513 (14)	−0.07899 (8)	0.42314 (6)	0.0208 (2)
H1	0.2236	−0.0805	0.3767	0.025*
N2	0.27932 (14)	0.00518 (8)	0.46840 (6)	0.0204 (2)
C11	0.09647 (17)	−0.16584 (10)	0.45033 (7)	0.0204 (2)
C12	0.03244 (17)	−0.26207 (10)	0.40840 (8)	0.0212 (3)
S12	0.06747 (4)	−0.28685 (2)	0.315759 (18)	0.02165 (8)
O121	−0.10261 (14)	−0.31498 (11)	0.27063 (6)	0.0400 (3)
O122	0.17794 (17)	−0.19053 (8)	0.29539 (6)	0.0388 (3)
O123	0.14749 (15)	−0.37448 (9)	0.32177 (6)	0.0345 (2)
C13	−0.07003 (18)	−0.34673 (10)	0.43951 (8)	0.0241 (3)
H13	−0.1107	−0.4117	0.4111	0.029*
C14	−0.11575 (18)	−0.34124 (11)	0.50956 (8)	0.0244 (3)
C141	−0.2285 (2)	−0.43411 (12)	0.54011 (9)	0.0329 (3)
H14A	−0.2619	−0.4935	0.5032	0.049*
H14B	−0.3318	−0.4153	0.5506	0.049*
H14C	−0.1654	−0.4541	0.5865	0.049*
C15	−0.05199 (17)	−0.24310 (11)	0.54868 (8)	0.0230 (3)
Cl15	−0.10530 (4)	−0.22738 (3)	0.636744 (19)	0.02741 (8)
C16	0.05074 (17)	−0.15709 (10)	0.52086 (8)	0.0225 (3)
H16	0.0903	−0.0922	0.5494	0.027*
C21	0.38104 (17)	0.08488 (10)	0.44246 (7)	0.0207 (2)
C22	0.42560 (17)	0.09699 (10)	0.36708 (7)	0.0212 (3)
O22	0.38209 (13)	0.03244 (7)	0.31365 (5)	0.0258 (2)
N23	0.52994 (15)	0.19786 (9)	0.37048 (6)	0.0223 (2)
N24	0.55559 (15)	0.24935 (9)	0.44178 (6)	0.0235 (2)
C25	0.46907 (17)	0.18362 (10)	0.48347 (8)	0.0222 (3)
C26	0.46591 (19)	0.21245 (11)	0.56252 (8)	0.0274 (3)
H26A	0.5412	0.2829	0.5762	0.041*
H26B	0.5063	0.1612	0.5956	0.041*
H26C	0.3482	0.2122	0.5679	0.041*
C31	0.59883 (17)	0.25518 (10)	0.31182 (7)	0.0202 (2)
C32	0.52121 (17)	0.22746 (10)	0.23780 (7)	0.0210 (3)
H32	0.4243	0.1689	0.2261	0.025*
C33	0.58757 (17)	0.28679 (10)	0.18087 (7)	0.0192 (2)
S33	0.48027 (4)	0.25034 (2)	0.087161 (18)	0.02021 (7)
O331	0.53662 (15)	0.15857 (7)	0.06617 (6)	0.0296 (2)
O332	0.54198 (13)	0.33916 (7)	0.04209 (5)	0.0250 (2)
O333	0.29874 (13)	0.22793 (9)	0.08923 (6)	0.0320 (2)
C34	0.72861 (17)	0.37296 (10)	0.19700 (8)	0.0211 (3)
H34	0.7726	0.4129	0.1578	0.025*
C35	0.80425 (17)	0.39964 (10)	0.27144 (8)	0.0226 (3)
H35	0.9006	0.4586	0.2831	0.027*
C36	0.74125 (17)	0.34156 (10)	0.32903 (8)	0.0218 (3)
H36	0.7944	0.3603	0.3797	0.026*
Ca1	0.5000	0.0000	0.0000	0.01873 (8)
Ca2	0.5000	0.5000	0.0000	0.01873 (8)
O1A	0.79542 (13)	0.03686 (8)	0.01883 (6)	0.0293 (2)
C1A	0.92169 (19)	0.04889 (12)	0.07032 (9)	0.0304 (3)
H1A	0.9928	0.1183	0.0810	0.036*
N1A	0.96504 (16)	−0.02624 (10)	0.11123 (7)	0.0294 (3)
C2A	1.1200 (2)	−0.00658 (16)	0.16736 (12)	0.0488 (5)
H2A1	1.2063	−0.0356	0.1489	0.073*
H2A2	1.0934	−0.0404	0.2136	0.073*
H2A3	1.1652	0.0695	0.1776	0.073*
C3A	0.8731 (2)	−0.13714 (12)	0.09459 (10)	0.0338 (3)
H3A1	0.7527	−0.1417	0.0728	0.051*
H3A2	0.8782	−0.1755	0.1409	0.051*
H3A3	0.9268	−0.1683	0.0589	0.051*
O1B	0.51786 (13)	−0.06538 (7)	0.11988 (5)	0.0252 (2)
C1B	0.61063 (18)	−0.02255 (11)	0.17863 (8)	0.0246 (3)
H1B	0.6549	0.0517	0.1802	0.029*
N1B	0.65205 (15)	−0.07317 (9)	0.23916 (6)	0.0238 (2)
C2B	0.7593 (2)	−0.01713 (13)	0.30634 (9)	0.0362 (4)
H2B1	0.7967	0.0579	0.2969	0.054*
H2B2	0.8601	−0.0457	0.3202	0.054*
H2B3	0.6933	−0.0257	0.3474	0.054*
C3B	0.5807 (2)	−0.18619 (11)	0.24202 (9)	0.0305 (3)
H3B1	0.4792	−0.1988	0.2662	0.046*
H3B2	0.6672	−0.2179	0.2708	0.046*
H3B3	0.5478	−0.2180	0.1910	0.046*
O1C	0.41319 (13)	0.52141 (8)	0.11269 (6)	0.0277 (2)
C1C	0.48527 (18)	0.54202 (10)	0.17886 (8)	0.0232 (3)
H1C	0.5995	0.5851	0.1885	0.028*
N1C	0.41158 (15)	0.50722 (9)	0.23661 (7)	0.0239 (2)
C2C	0.2386 (2)	0.43748 (13)	0.22386 (9)	0.0344 (3)
H2C1	0.1542	0.4790	0.2095	0.052*
H2C2	0.2171	0.4015	0.2699	0.052*
H2C3	0.2285	0.3851	0.1836	0.052*
C3C	0.4973 (2)	0.53733 (12)	0.31343 (8)	0.0293 (3)
H3C1	0.6121	0.5832	0.3135	0.044*
H3C2	0.5076	0.4740	0.3406	0.044*
H3C3	0.4299	0.5751	0.3380	0.044*
O1D	0.77525 (13)	0.56605 (8)	0.06282 (6)	0.0297 (2)
C1D	0.92133 (19)	0.61735 (11)	0.09213 (8)	0.0261 (3)
H1D	0.9443	0.6296	0.1450	0.031*
N1D	1.04673 (15)	0.65600 (9)	0.05487 (7)	0.0233 (2)
C2D	1.2114 (2)	0.72099 (13)	0.09251 (11)	0.0365 (4)
H2D1	1.2124	0.7244	0.1466	0.055*
H2D2	1.2287	0.7922	0.0737	0.055*
H2D3	1.3040	0.6901	0.0826	0.055*
C3D	1.0203 (2)	0.64251 (13)	−0.02645 (9)	0.0333 (3)
H3D1	0.9141	0.5882	−0.0440	0.050*
H3D2	1.1177	0.6210	−0.0411	0.050*
H3D3	1.0112	0.7093	−0.0490	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0245 (5)	0.0201 (5)	0.0171 (5)	0.0036 (4)	0.0049 (4)	0.0011 (4)
N2	0.0215 (5)	0.0205 (5)	0.0188 (5)	0.0055 (4)	0.0019 (4)	0.0011 (4)
C11	0.0205 (6)	0.0207 (6)	0.0199 (6)	0.0054 (5)	0.0032 (5)	0.0040 (5)
C12	0.0218 (6)	0.0218 (6)	0.0199 (6)	0.0058 (5)	0.0026 (5)	0.0021 (5)
S12	0.02296 (16)	0.02154 (15)	0.01942 (16)	0.00347 (12)	0.00389 (12)	−0.00075 (11)
O121	0.0272 (5)	0.0683 (8)	0.0230 (5)	0.0119 (5)	0.0001 (4)	−0.0058 (5)
O122	0.0613 (8)	0.0255 (5)	0.0262 (6)	−0.0040 (5)	0.0196 (5)	−0.0026 (4)
O123	0.0413 (6)	0.0343 (6)	0.0335 (6)	0.0175 (5)	0.0104 (5)	0.0012 (5)
C13	0.0251 (7)	0.0212 (6)	0.0243 (7)	0.0038 (5)	0.0028 (5)	0.0016 (5)
C14	0.0240 (6)	0.0244 (6)	0.0242 (7)	0.0052 (5)	0.0036 (5)	0.0061 (5)
C141	0.0364 (8)	0.0290 (7)	0.0307 (8)	0.0000 (6)	0.0105 (6)	0.0065 (6)
C15	0.0232 (6)	0.0281 (6)	0.0192 (6)	0.0087 (5)	0.0048 (5)	0.0043 (5)
Cl15	0.02945 (17)	0.03359 (17)	0.02084 (16)	0.00790 (13)	0.00885 (12)	0.00564 (13)
C16	0.0236 (6)	0.0233 (6)	0.0208 (6)	0.0067 (5)	0.0029 (5)	0.0016 (5)
C21	0.0229 (6)	0.0216 (6)	0.0174 (6)	0.0061 (5)	0.0025 (5)	0.0010 (5)
C22	0.0232 (6)	0.0198 (6)	0.0200 (6)	0.0039 (5)	0.0039 (5)	0.0029 (5)
O22	0.0343 (5)	0.0210 (4)	0.0196 (5)	0.0009 (4)	0.0067 (4)	−0.0009 (4)
N23	0.0264 (6)	0.0211 (5)	0.0170 (5)	0.0005 (4)	0.0048 (4)	−0.0003 (4)
N24	0.0262 (6)	0.0243 (5)	0.0177 (5)	0.0029 (4)	0.0027 (4)	−0.0023 (4)
C25	0.0231 (6)	0.0229 (6)	0.0193 (6)	0.0046 (5)	0.0015 (5)	−0.0001 (5)
C26	0.0311 (7)	0.0295 (7)	0.0198 (7)	0.0046 (6)	0.0042 (5)	−0.0021 (5)
C31	0.0220 (6)	0.0186 (6)	0.0204 (6)	0.0046 (5)	0.0054 (5)	0.0022 (5)
C32	0.0224 (6)	0.0170 (5)	0.0221 (6)	0.0020 (5)	0.0043 (5)	0.0009 (5)
C33	0.0222 (6)	0.0168 (5)	0.0190 (6)	0.0057 (5)	0.0034 (5)	0.0008 (4)
S33	0.02539 (16)	0.01527 (14)	0.01799 (15)	0.00280 (11)	0.00160 (12)	0.00145 (11)
O331	0.0463 (6)	0.0181 (4)	0.0232 (5)	0.0104 (4)	−0.0003 (4)	−0.0024 (4)
O332	0.0356 (5)	0.0174 (4)	0.0212 (5)	0.0050 (4)	0.0048 (4)	0.0035 (4)
O333	0.0250 (5)	0.0394 (6)	0.0264 (5)	0.0011 (4)	0.0002 (4)	0.0038 (4)
C34	0.0221 (6)	0.0176 (5)	0.0235 (7)	0.0037 (5)	0.0060 (5)	0.0021 (5)
C35	0.0208 (6)	0.0183 (6)	0.0266 (7)	0.0011 (5)	0.0038 (5)	−0.0001 (5)
C36	0.0217 (6)	0.0208 (6)	0.0215 (6)	0.0042 (5)	0.0019 (5)	−0.0018 (5)
Ca1	0.02234 (17)	0.01492 (15)	0.01722 (17)	0.00424 (13)	−0.00070 (13)	0.00054 (12)
Ca2	0.02322 (18)	0.01580 (15)	0.01673 (17)	0.00299 (13)	0.00499 (13)	0.00235 (12)
O1A	0.0244 (5)	0.0328 (5)	0.0290 (5)	0.0066 (4)	0.0007 (4)	0.0035 (4)
C1A	0.0257 (7)	0.0308 (7)	0.0327 (8)	0.0035 (6)	0.0047 (6)	0.0027 (6)
N1A	0.0225 (6)	0.0343 (6)	0.0293 (7)	0.0050 (5)	0.0016 (5)	0.0048 (5)
C2A	0.0343 (9)	0.0513 (10)	0.0494 (11)	0.0018 (8)	−0.0114 (8)	0.0154 (9)
C3A	0.0346 (8)	0.0293 (7)	0.0384 (9)	0.0125 (6)	0.0026 (6)	−0.0002 (6)
O1B	0.0287 (5)	0.0243 (5)	0.0203 (5)	0.0052 (4)	−0.0003 (4)	0.0030 (4)
C1B	0.0285 (7)	0.0221 (6)	0.0233 (7)	0.0070 (5)	0.0040 (5)	0.0018 (5)
N1B	0.0260 (6)	0.0252 (5)	0.0190 (6)	0.0055 (5)	0.0018 (4)	0.0019 (4)
C2B	0.0405 (9)	0.0384 (8)	0.0230 (7)	0.0040 (7)	−0.0042 (6)	−0.0011 (6)
C3B	0.0363 (8)	0.0272 (7)	0.0255 (7)	0.0054 (6)	0.0019 (6)	0.0071 (6)
O1C	0.0334 (5)	0.0301 (5)	0.0209 (5)	0.0080 (4)	0.0086 (4)	0.0008 (4)
C1C	0.0271 (7)	0.0208 (6)	0.0241 (7)	0.0074 (5)	0.0088 (5)	0.0015 (5)
N1C	0.0273 (6)	0.0242 (5)	0.0209 (6)	0.0059 (5)	0.0074 (5)	0.0001 (4)
C2C	0.0335 (8)	0.0356 (8)	0.0319 (8)	−0.0009 (6)	0.0135 (6)	−0.0004 (6)
C3C	0.0335 (8)	0.0364 (7)	0.0204 (7)	0.0135 (6)	0.0046 (6)	0.0007 (6)
O1D	0.0251 (5)	0.0273 (5)	0.0319 (6)	−0.0015 (4)	0.0039 (4)	0.0015 (4)
C1D	0.0286 (7)	0.0236 (6)	0.0249 (7)	0.0050 (5)	0.0036 (5)	0.0017 (5)
N1D	0.0215 (5)	0.0203 (5)	0.0267 (6)	0.0034 (4)	0.0034 (4)	0.0004 (4)
C2D	0.0229 (7)	0.0346 (8)	0.0477 (10)	0.0008 (6)	0.0036 (6)	−0.0102 (7)
C3D	0.0368 (8)	0.0377 (8)	0.0276 (8)	0.0104 (7)	0.0096 (6)	0.0048 (6)

Geometric parameters (Å, º)

N1—N2	1.3250 (15)	Ca1—O1B	2.3320 (10)
N1—C11	1.4068 (17)	Ca1—O1B^i	2.3320 (10)
N1—H1	0.8800	Ca2—O1D^ii	2.2920 (10)
N2—C21	1.3074 (17)	Ca2—O1D	2.2920 (10)
C11—C16	1.4026 (19)	Ca2—O1C^ii	2.3095 (10)
C11—C12	1.4066 (18)	Ca2—O1C	2.3096 (10)
C12—C13	1.3981 (19)	Ca2—O332^ii	2.3266 (9)
C12—S12	1.7919 (14)	O1A—C1A	1.2443 (19)
S12—O121	1.4453 (11)	C1A—N1A	1.315 (2)
S12—O122	1.4485 (11)	C1A—H1A	0.9500
S12—O123	1.4487 (11)	N1A—C2A	1.449 (2)
C13—C14	1.389 (2)	N1A—C3A	1.467 (2)
C13—H13	0.9500	C2A—H2A1	0.9800
C14—C15	1.4036 (19)	C2A—H2A2	0.9800
C14—C141	1.5033 (19)	C2A—H2A3	0.9800
C141—H14A	0.9800	C3A—H3A1	0.9800
C141—H14B	0.9800	C3A—H3A2	0.9800
C141—H14C	0.9800	C3A—H3A3	0.9800
C15—C16	1.3817 (19)	O1B—C1B	1.2395 (17)
C15—Cl15	1.7480 (14)	C1B—N1B	1.3209 (19)
C16—H16	0.9500	C1B—H1B	0.9500
C21—C25	1.4495 (18)	N1B—C2B	1.4511 (18)
C21—C22	1.4711 (18)	N1B—C3B	1.4570 (18)
C22—O22	1.2295 (16)	C2B—H2B1	0.9800
C22—N23	1.3802 (16)	C2B—H2B2	0.9800
N23—N24	1.4156 (15)	C2B—H2B3	0.9800
N23—C31	1.4174 (17)	C3B—H3B1	0.9800
N24—C25	1.3023 (18)	C3B—H3B2	0.9800
C25—C26	1.4867 (19)	C3B—H3B3	0.9800
C26—H26A	0.9800	O1C—C1C	1.2402 (17)
C26—H26B	0.9800	C1C—N1C	1.3210 (18)
C26—H26C	0.9800	C1C—H1C	0.9500
C31—C32	1.3889 (19)	N1C—C3C	1.4540 (18)
C31—C36	1.3990 (18)	N1C—C2C	1.4602 (19)
C32—C33	1.3958 (18)	C2C—H2C1	0.9800
C32—H32	0.9500	C2C—H2C2	0.9800
C33—C34	1.3891 (17)	C2C—H2C3	0.9800
C33—S33	1.7790 (13)	C3C—H3C1	0.9800
S33—O333	1.4427 (11)	C3C—H3C2	0.9800
S33—O331	1.4592 (10)	C3C—H3C3	0.9800
S33—O332	1.4601 (10)	O1D—C1D	1.2420 (18)
O331—Ca1	2.3256 (9)	C1D—N1D	1.3185 (19)
O332—Ca2	2.3266 (9)	C1D—H1D	0.9500
C34—C35	1.3901 (19)	N1D—C2D	1.4553 (18)
C34—H34	0.9500	N1D—C3D	1.457 (2)
C35—C36	1.3879 (19)	C2D—H2D1	0.9800
C35—H35	0.9500	C2D—H2D2	0.9800
C36—H36	0.9500	C2D—H2D3	0.9800
Ca1—O1A	2.3010 (10)	C3D—H3D1	0.9800
Ca1—O1A^i	2.3010 (10)	C3D—H3D2	0.9800
Ca1—O331^i	2.3256 (9)	C3D—H3D3	0.9800
N2—N1—C11	119.04 (11)	O1B—Ca1—O1B^i	180.0
N2—N1—H1	120.5	O1D^ii—Ca2—O1D	180.0
C11—N1—H1	120.5	O1D^ii—Ca2—O1C^ii	86.40 (4)
C21—N2—N1	118.28 (11)	O1D—Ca2—O1C^ii	93.60 (4)
C16—C11—C12	118.88 (12)	O1D^ii—Ca2—O1C	93.60 (4)
C16—C11—N1	119.67 (11)	O1D—Ca2—O1C	86.40 (4)
C12—C11—N1	121.45 (12)	O1C^ii—Ca2—O1C	180.0
C13—C12—C11	118.82 (12)	O1D^ii—Ca2—O332^ii	84.14 (4)
C13—C12—S12	115.60 (10)	O1D—Ca2—O332^ii	95.86 (4)
C11—C12—S12	125.57 (10)	O1C^ii—Ca2—O332^ii	86.60 (4)
O121—S12—O122	114.27 (8)	O1C—Ca2—O332^ii	93.40 (4)
O121—S12—O123	112.06 (7)	O1D^ii—Ca2—O332	95.86 (4)
O122—S12—O123	113.24 (7)	O1D—Ca2—O332	84.14 (4)
O121—S12—C12	104.67 (6)	O1C^ii—Ca2—O332	93.40 (4)
O122—S12—C12	106.31 (6)	O1C—Ca2—O332	86.60 (4)
O123—S12—C12	105.29 (6)	O332^ii—Ca2—O332	180.0
C14—C13—C12	123.77 (12)	C1A—O1A—Ca1	140.67 (10)
C14—C13—H13	118.1	O1A—C1A—N1A	125.55 (14)
C12—C13—H13	118.1	O1A—C1A—H1A	117.2
C13—C14—C15	115.41 (12)	N1A—C1A—H1A	117.2
C13—C14—C141	121.77 (13)	C1A—N1A—C2A	122.05 (14)
C15—C14—C141	122.81 (13)	C1A—N1A—C3A	121.28 (13)
C14—C141—H14A	109.5	C2A—N1A—C3A	116.04 (14)
C14—C141—H14B	109.5	N1A—C2A—H2A1	109.5
H14A—C141—H14B	109.5	N1A—C2A—H2A2	109.5
C14—C141—H14C	109.5	H2A1—C2A—H2A2	109.5
H14A—C141—H14C	109.5	N1A—C2A—H2A3	109.5
H14B—C141—H14C	109.5	H2A1—C2A—H2A3	109.5
C16—C15—C14	123.24 (13)	H2A2—C2A—H2A3	109.5
C16—C15—Cl15	117.80 (10)	N1A—C3A—H3A1	109.5
C14—C15—Cl15	118.96 (11)	N1A—C3A—H3A2	109.5
C15—C16—C11	119.84 (12)	H3A1—C3A—H3A2	109.5
C15—C16—H16	120.1	N1A—C3A—H3A3	109.5
C11—C16—H16	120.1	H3A1—C3A—H3A3	109.5
N2—C21—C25	125.57 (12)	H3A2—C3A—H3A3	109.5
N2—C21—C22	128.92 (12)	C1B—O1B—Ca1	127.90 (9)
C25—C21—C22	105.46 (11)	O1B—C1B—N1B	124.44 (13)
O22—C22—N23	127.87 (13)	O1B—C1B—H1B	117.8
O22—C22—C21	128.43 (12)	N1B—C1B—H1B	117.8
N23—C22—C21	103.70 (11)	C1B—N1B—C2B	121.18 (12)
C22—N23—N24	112.52 (11)	C1B—N1B—C3B	120.62 (12)
C22—N23—C31	128.47 (11)	C2B—N1B—C3B	118.05 (12)
N24—N23—C31	118.80 (10)	N1B—C2B—H2B1	109.5
C25—N24—N23	106.96 (10)	N1B—C2B—H2B2	109.5
N24—C25—C21	111.36 (12)	H2B1—C2B—H2B2	109.5
N24—C25—C26	121.50 (12)	N1B—C2B—H2B3	109.5
C21—C25—C26	127.14 (12)	H2B1—C2B—H2B3	109.5
C25—C26—H26A	109.5	H2B2—C2B—H2B3	109.5
C25—C26—H26B	109.5	N1B—C3B—H3B1	109.5
H26A—C26—H26B	109.5	N1B—C3B—H3B2	109.5
C25—C26—H26C	109.5	H3B1—C3B—H3B2	109.5
H26A—C26—H26C	109.5	N1B—C3B—H3B3	109.5
H26B—C26—H26C	109.5	H3B1—C3B—H3B3	109.5
C32—C31—C36	120.41 (12)	H3B2—C3B—H3B3	109.5
C32—C31—N23	119.85 (11)	C1C—O1C—Ca2	135.83 (9)
C36—C31—N23	119.71 (12)	O1C—C1C—N1C	123.46 (13)
C31—C32—C33	119.08 (12)	O1C—C1C—H1C	118.3
C31—C32—H32	120.5	N1C—C1C—H1C	118.3
C33—C32—H32	120.5	C1C—N1C—C3C	121.81 (12)
C34—C33—C32	121.24 (12)	C1C—N1C—C2C	119.77 (12)
C34—C33—S33	121.33 (10)	C3C—N1C—C2C	118.42 (12)
C32—C33—S33	117.40 (10)	N1C—C2C—H2C1	109.5
O333—S33—O331	113.57 (7)	N1C—C2C—H2C2	109.5
O333—S33—O332	114.30 (6)	H2C1—C2C—H2C2	109.5
O331—S33—O332	110.50 (6)	N1C—C2C—H2C3	109.5
O333—S33—C33	106.11 (6)	H2C1—C2C—H2C3	109.5
O331—S33—C33	105.32 (6)	H2C2—C2C—H2C3	109.5
O332—S33—C33	106.26 (6)	N1C—C3C—H3C1	109.5
S33—O331—Ca1	153.35 (7)	N1C—C3C—H3C2	109.5
S33—O332—Ca2	144.51 (6)	H3C1—C3C—H3C2	109.5
C33—C34—C35	118.83 (12)	N1C—C3C—H3C3	109.5
C33—C34—H34	120.6	H3C1—C3C—H3C3	109.5
C35—C34—H34	120.6	H3C2—C3C—H3C3	109.5
C36—C35—C34	121.03 (12)	C1D—O1D—Ca2	169.55 (10)
C36—C35—H35	119.5	O1D—C1D—N1D	124.47 (14)
C34—C35—H35	119.5	O1D—C1D—H1D	117.8
C35—C36—C31	119.41 (12)	N1D—C1D—H1D	117.8
C35—C36—H36	120.3	C1D—N1D—C2D	121.35 (13)
C31—C36—H36	120.3	C1D—N1D—C3D	120.97 (12)
O1A—Ca1—O1A^i	180.0	C2D—N1D—C3D	117.48 (13)
O1A—Ca1—O331	86.13 (4)	N1D—C2D—H2D1	109.5
O1A^i—Ca1—O331	93.86 (4)	N1D—C2D—H2D2	109.5
O1A—Ca1—O331^i	93.87 (4)	H2D1—C2D—H2D2	109.5
O1A^i—Ca1—O331^i	86.14 (4)	N1D—C2D—H2D3	109.5
O331—Ca1—O331^i	180.00 (7)	H2D1—C2D—H2D3	109.5
O1A—Ca1—O1B	87.13 (4)	H2D2—C2D—H2D3	109.5
O1A^i—Ca1—O1B	92.87 (4)	N1D—C3D—H3D1	109.5
O331—Ca1—O1B	82.48 (4)	N1D—C3D—H3D2	109.5
O331^i—Ca1—O1B	97.52 (4)	H3D1—C3D—H3D2	109.5
O1A—Ca1—O1B^i	92.87 (4)	N1D—C3D—H3D3	109.5
O1A^i—Ca1—O1B^i	87.13 (4)	H3D1—C3D—H3D3	109.5
O331—Ca1—O1B^i	97.52 (4)	H3D2—C3D—H3D3	109.5
O331^i—Ca1—O1B^i	82.48 (4)
C11—N1—N2—C21	179.44 (12)	C32—C33—S33—O332	164.54 (10)
N2—N1—C11—C16	8.27 (18)	O333—S33—O331—Ca1	34.92 (17)
N2—N1—C11—C12	−171.53 (12)	O332—S33—O331—Ca1	−95.05 (16)
C16—C11—C12—C13	−2.06 (19)	C33—S33—O331—Ca1	150.60 (15)
N1—C11—C12—C13	177.75 (12)	O333—S33—O332—Ca2	30.36 (12)
C16—C11—C12—S12	176.83 (10)	O331—S33—O332—Ca2	159.93 (9)
N1—C11—C12—S12	−3.36 (19)	C33—S33—O332—Ca2	−86.31 (11)
C13—C12—S12—O121	59.72 (12)	C32—C33—C34—C35	0.18 (19)
C11—C12—S12—O121	−119.20 (13)	S33—C33—C34—C35	178.11 (10)
C13—C12—S12—O122	−178.99 (11)	C33—C34—C35—C36	0.2 (2)
C11—C12—S12—O122	2.09 (14)	C34—C35—C36—C31	−0.3 (2)
C13—C12—S12—O123	−58.57 (12)	C32—C31—C36—C35	0.2 (2)
C11—C12—S12—O123	122.50 (12)	N23—C31—C36—C35	−177.70 (12)
C11—C12—C13—C14	1.2 (2)	S33—O331—Ca1—O1A	156.84 (16)
S12—C12—C13—C14	−177.80 (11)	S33—O331—Ca1—O1A^i	−23.16 (16)
C12—C13—C14—C15	0.1 (2)	S33—O331—Ca1—O331^i	−100 (100)
C12—C13—C14—C141	179.06 (14)	S33—O331—Ca1—O1B	−115.55 (16)
C13—C14—C15—C16	−0.6 (2)	S33—O331—Ca1—O1B^i	64.45 (16)
C141—C14—C15—C16	−179.53 (14)	S33—O332—Ca2—O1D^ii	−60.58 (11)
C13—C14—C15—Cl15	178.92 (10)	S33—O332—Ca2—O1D	119.42 (11)
C141—C14—C15—Cl15	0.00 (19)	S33—O332—Ca2—O1C^ii	−147.30 (10)
C14—C15—C16—C11	−0.3 (2)	S33—O332—Ca2—O1C	32.70 (10)
Cl15—C15—C16—C11	−179.81 (10)	S33—O332—Ca2—O332^ii	23 (8)
C12—C11—C16—C15	1.6 (2)	O1A^i—Ca1—O1A—C1A	104 (3)
N1—C11—C16—C15	−178.18 (12)	O331—Ca1—O1A—C1A	63.87 (16)
N1—N2—C21—C25	178.45 (12)	O331^i—Ca1—O1A—C1A	−116.13 (16)
N1—N2—C21—C22	1.3 (2)	O1B—Ca1—O1A—C1A	−18.78 (16)
N2—C21—C22—O22	−3.6 (2)	O1B^i—Ca1—O1A—C1A	161.22 (16)
C25—C21—C22—O22	178.78 (14)	Ca1—O1A—C1A—N1A	70.6 (2)
N2—C21—C22—N23	177.11 (13)	O1A—C1A—N1A—C2A	176.35 (17)
C25—C21—C22—N23	−0.53 (14)	O1A—C1A—N1A—C3A	5.8 (2)
O22—C22—N23—N24	−178.76 (13)	O1A—Ca1—O1B—C1B	49.30 (12)
C21—C22—N23—N24	0.56 (15)	O1A^i—Ca1—O1B—C1B	−130.70 (12)
O22—C22—N23—C31	6.6 (2)	O331—Ca1—O1B—C1B	−37.18 (12)
C21—C22—N23—C31	−174.07 (13)	O331^i—Ca1—O1B—C1B	142.82 (12)
C22—N23—N24—C25	−0.36 (16)	O1B^i—Ca1—O1B—C1B	146 (12)
C31—N23—N24—C25	174.84 (12)	Ca1—O1B—C1B—N1B	−159.63 (11)
N23—N24—C25—C21	−0.02 (15)	O1B—C1B—N1B—C2B	−178.97 (14)
N23—N24—C25—C26	−179.46 (12)	O1B—C1B—N1B—C3B	−3.5 (2)
N2—C21—C25—N24	−177.39 (13)	O1D^ii—Ca2—O1C—C1C	169.34 (13)
C22—C21—C25—N24	0.35 (16)	O1D—Ca2—O1C—C1C	−10.66 (13)
N2—C21—C25—C26	2.0 (2)	O1C^ii—Ca2—O1C—C1C	−12 (36)
C22—C21—C25—C26	179.76 (13)	O332^ii—Ca2—O1C—C1C	−106.33 (13)
C22—N23—C31—C32	21.7 (2)	O332—Ca2—O1C—C1C	73.67 (13)
N24—N23—C31—C32	−152.61 (12)	Ca2—O1C—C1C—N1C	−149.29 (11)
C22—N23—C31—C36	−160.40 (13)	O1C—C1C—N1C—C3C	−176.95 (13)
N24—N23—C31—C36	25.27 (18)	O1C—C1C—N1C—C2C	2.4 (2)
C36—C31—C32—C33	0.17 (19)	O1D^ii—Ca2—O1D—C1D	54 (20)
N23—C31—C32—C33	178.04 (12)	O1C^ii—Ca2—O1D—C1D	83.0 (6)
C31—C32—C33—C34	−0.35 (19)	O1C—Ca2—O1D—C1D	−97.0 (6)
C31—C32—C33—S33	−178.36 (10)	O332^ii—Ca2—O1D—C1D	−4.0 (6)
C34—C33—S33—O333	−135.50 (11)	O332—Ca2—O1D—C1D	176.1 (6)
C32—C33—S33—O333	42.51 (12)	Ca2—O1D—C1D—N1D	−69.8 (6)
C34—C33—S33—O331	103.79 (11)	O1D—C1D—N1D—C2D	176.12 (14)
C32—C33—S33—O331	−78.20 (11)	O1D—C1D—N1D—C3D	1.4 (2)
C34—C33—S33—O332	−13.47 (12)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O122	0.88	1.98	2.6828 (15)	136
N1—H1···O22	0.88	2.18	2.8462 (15)	133