Interplay of hydrogen bonding and coordination modes in di­aqua­bis(8-hydroxy-7-iodo­quinoline-5-sulfonato)­calcium(II) monohydrate

In the crystal structure of the title compound, [Ca(C₉H₅INO₄S)₂(H₂O)₂]·H₂O, the asymmetric unit consists of one calcium ion, two organic ligands, two coordinated water mol­ecules and one uncoordinated water mol­ecule. The calcium ion has a pentagonal-bipyramidal geometry, formed by O atoms of three different sulfonate groups, deprotonated O atoms of two different oxine rings and two water mol­ecules. In the ligands of type I, two O atoms of the sulfonate group are involved in coordination, whereas in type II ligands, only one O atom is involved. Ligands of type I are stacked over one another, each pair of adjacent members of the stack being related by an inversion centre. Ligands of type II are also stacked in a similar manner. Both of these molecular stacks are cross-linked by Ca—O(sulfonate) and Ca—O(quinolinol) bonds, leading to a three-dimensional network. This network is further stabilized by a number of O—H...O and N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.066
• wR factor = 0.103
• Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT761_ALERT_1_A CIF Contains no X-H Bonds ......................          ?
PLAT762_ALERT_1_A CIF Contains no X-Y-H or H-Y-H Angles ..........          ?

Alert level B
CELLV02_ALERT_1_B  The supplied cell volume s.u. differs from that
            calculated from the cell parameter s.u.'s by > 4
            Calculated cell volume su =      10.12
            Cell volume su given      =       4.00

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?

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

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

---

Computing details

Data collection: KM-4 CCD Software (Kuma, 1999); cell refinement: KM-4 CCD Software; data reduction: KM-4 CCD Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1997); software used to prepare material for publication: SHELXL97.

Diaquabis(µ-8-hydroxy-7-iodoquinoline-5-sulfonato)calcium(II) monohydrate

Crystal data

[Ca(C9H5INO4S)2(H2O)2]H2O	F(000) = 1536
Mr = 794.35	Dx = 2.182 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10575 reflections
a = 20.326 (4) Å	θ = 3.1–26.1°
b = 6.958 (1) Å	µ = 3.05 mm^−1
c = 19.219 (4) Å	T = 293 K
β = 117.19 (3)°	Plate, red
V = 2417.7 (4) Å^3	0.40 × 0.15 × 0.05 mm
Z = 4

Data collection

Kuma KM-4 CCD κ-geometry diffractometer	4771 independent reflections
Radiation source: fine-focus sealed tube	4526 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
w scans	θmax = 26.1°, θmin = 3.1°
Absorption correction: multi-scan (XEMP; Siemens, 1990)	h = −24→25
Tmin = 0.593, Tmax = 0.859	k = −8→5
26674 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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.103	H-atom parameters constrained
S = 1.36	w = 1/[σ^2(Fo^2) + (0.0351P)^2 + 1.7598P] where P = (Fo^2 + 2Fc^2)/3
4771 reflections	(Δ/σ)max = 0.002
325 parameters	Δρmax = 1.61 e Å^−3
0 restraints	Δρmin = −0.88 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
I1	0.39873 (2)	1.11688 (7)	0.50962 (2)	0.0316 (1)
I2	1.10907 (2)	0.44831 (8)	1.27273 (2)	0.0401 (2)
Ca	0.74517 (6)	0.61074 (17)	0.85379 (7)	0.0181 (3)
S1	0.69333 (7)	1.1018 (2)	0.76432 (8)	0.0171 (4)
S2	0.81681 (8)	0.3093 (2)	1.03438 (8)	0.0190 (4)
O1	0.7776 (2)	0.3650 (6)	0.9525 (2)	0.0256 (12)
O1W	0.6868 (2)	0.6495 (6)	0.7108 (2)	0.0242 (12)
O2	0.7970 (2)	0.1148 (6)	1.0466 (3)	0.0281 (12)
O2W	0.8021 (2)	0.7644 (6)	0.9872 (2)	0.0288 (14)
O3	0.8098 (2)	0.4473 (6)	1.0871 (2)	0.0271 (14)
O4	1.1364 (2)	0.3525 (6)	1.1235 (2)	0.0271 (14)
O21	0.6992 (2)	1.0448 (6)	0.6945 (2)	0.0231 (12)
O22	0.7213 (2)	1.2938 (6)	0.7902 (2)	0.0259 (12)
O23	0.7263 (2)	0.9616 (6)	0.8268 (2)	0.0223 (12)
O24	0.3705 (2)	1.1169 (6)	0.6609 (2)	0.0280 (14)
N1	1.0437 (3)	0.2360 (7)	0.9783 (3)	0.0223 (17)
N2	0.4628 (3)	1.1176 (7)	0.8140 (3)	0.0227 (17)
C2	1.0026 (3)	0.1770 (9)	0.9055 (4)	0.027 (2)
C3	0.9271 (3)	0.1495 (8)	0.8782 (4)	0.0259 (17)
C4	0.8957 (3)	0.1871 (8)	0.9260 (3)	0.0225 (17)
C5	0.9118 (3)	0.3045 (8)	1.0576 (3)	0.0200 (17)
C6	0.9618 (3)	0.3572 (8)	1.1329 (3)	0.0219 (19)
C7	1.0375 (3)	0.3688 (9)	1.1582 (3)	0.0215 (17)
C8	1.0685 (3)	0.3352 (8)	1.1067 (3)	0.0198 (17)
C9	0.9391 (3)	0.2556 (8)	1.0035 (3)	0.0172 (17)
C10	1.0159 (3)	0.2763 (8)	1.0290 (3)	0.0185 (17)
C22	0.5041 (4)	1.1198 (9)	0.8909 (4)	0.029 (2)
C23	0.5804 (3)	1.1206 (9)	0.9226 (4)	0.029 (2)
C24	0.6133 (3)	1.1181 (8)	0.8742 (3)	0.0232 (17)
C25	0.5971 (3)	1.1075 (8)	0.7362 (3)	0.0180 (17)
C26	0.5478 (3)	1.1100 (8)	0.6567 (3)	0.0214 (17)
C27	0.4715 (3)	1.1158 (8)	0.6299 (3)	0.0191 (17)
C28	0.4394 (3)	1.1156 (8)	0.6808 (3)	0.0188 (17)
C29	0.5697 (3)	1.1129 (8)	0.7918 (3)	0.0179 (17)
C30	0.4922 (3)	1.1151 (8)	0.7627 (3)	0.0190 (17)
O3W	0.6952 (2)	1.3834 (6)	0.6125 (2)	0.0309 (16)
H1	0.41370	1.13220	0.79560	0.0270*
H1W	0.69480	0.57210	0.68130	0.0290*
H2	0.48100	1.12230	0.92470	0.0350*
H2W	0.68410	0.75600	0.68800	0.0290*
H3	0.61040	1.12150	0.97830	0.0350*
H3W	0.80970	0.71580	1.03080	0.0350*
H4	0.66620	1.12070	0.89590	0.0280*
H4W	0.79350	0.87580	0.99910	0.0350*
H5	0.56680	1.10760	0.61930	0.0260*
H6	1.09080	0.27430	0.99500	0.0260*
H7	1.02480	0.15360	0.87160	0.0320*
H8	0.89720	0.10380	0.82590	0.0310*
H9	0.84360	0.16720	0.90740	0.0270*
H10	0.94330	0.38710	1.16950	0.0260*
H5W	0.70750	1.27890	0.63820	0.0370*
H6W	0.73140	1.38200	0.60180	0.0370*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0266 (2)	0.0434 (3)	0.0179 (2)	0.0013 (2)	0.0042 (2)	0.0003 (2)
I2	0.0259 (2)	0.0680 (4)	0.0207 (2)	−0.0093 (2)	0.0057 (2)	−0.0078 (2)
Ca	0.0130 (5)	0.0209 (6)	0.0189 (6)	0.0003 (5)	0.0060 (5)	0.0013 (5)
S1	0.0144 (7)	0.0153 (7)	0.0202 (7)	−0.0004 (6)	0.0066 (6)	−0.0002 (6)
S2	0.0153 (7)	0.0206 (8)	0.0208 (7)	−0.0022 (6)	0.0080 (6)	0.0001 (6)
O1	0.022 (2)	0.029 (2)	0.020 (2)	0.0034 (19)	0.0045 (18)	0.0057 (18)
O1W	0.034 (2)	0.019 (2)	0.022 (2)	0.0030 (18)	0.015 (2)	0.0004 (18)
O2	0.029 (2)	0.021 (2)	0.033 (2)	−0.0018 (19)	0.013 (2)	0.0016 (19)
O2W	0.039 (3)	0.021 (2)	0.030 (2)	0.003 (2)	0.019 (2)	−0.0015 (19)
O3	0.022 (2)	0.032 (3)	0.028 (2)	0.0003 (19)	0.0121 (19)	−0.0089 (19)
O4	0.014 (2)	0.039 (3)	0.028 (2)	−0.0035 (19)	0.0093 (18)	−0.002 (2)
O21	0.027 (2)	0.020 (2)	0.025 (2)	−0.0003 (18)	0.0143 (19)	−0.0025 (18)
O22	0.024 (2)	0.022 (2)	0.028 (2)	−0.0054 (18)	0.0088 (19)	−0.0016 (19)
O23	0.023 (2)	0.017 (2)	0.025 (2)	0.0041 (17)	0.0094 (18)	0.0061 (18)
O24	0.014 (2)	0.042 (3)	0.027 (2)	0.0011 (19)	0.0084 (18)	0.001 (2)
N1	0.020 (3)	0.023 (3)	0.023 (3)	−0.001 (2)	0.009 (2)	−0.002 (2)
N2	0.019 (3)	0.029 (3)	0.021 (3)	0.003 (2)	0.010 (2)	0.001 (2)
C2	0.035 (4)	0.022 (3)	0.031 (4)	0.003 (3)	0.022 (3)	0.002 (3)
C3	0.030 (3)	0.020 (3)	0.023 (3)	0.001 (3)	0.008 (3)	−0.005 (3)
C4	0.018 (3)	0.021 (3)	0.026 (3)	−0.002 (3)	0.008 (3)	−0.001 (3)
C5	0.016 (3)	0.020 (3)	0.023 (3)	−0.001 (2)	0.008 (2)	0.001 (2)
C6	0.019 (3)	0.028 (4)	0.020 (3)	−0.001 (3)	0.010 (2)	0.003 (3)
C7	0.018 (3)	0.026 (3)	0.017 (3)	−0.001 (3)	0.005 (2)	−0.002 (3)
C8	0.015 (3)	0.022 (3)	0.020 (3)	0.002 (2)	0.006 (2)	0.005 (2)
C9	0.015 (3)	0.014 (3)	0.023 (3)	−0.002 (2)	0.009 (2)	0.002 (2)
C10	0.021 (3)	0.015 (3)	0.022 (3)	0.002 (2)	0.012 (3)	0.005 (2)
C22	0.033 (4)	0.035 (4)	0.021 (3)	0.000 (3)	0.014 (3)	−0.001 (3)
C23	0.030 (4)	0.035 (4)	0.020 (3)	0.002 (3)	0.009 (3)	0.001 (3)
C24	0.016 (3)	0.025 (3)	0.023 (3)	−0.003 (3)	0.004 (3)	0.001 (3)
C25	0.017 (3)	0.015 (3)	0.024 (3)	−0.001 (2)	0.011 (2)	−0.003 (2)
C26	0.022 (3)	0.020 (3)	0.024 (3)	0.001 (3)	0.012 (3)	0.001 (3)
C27	0.016 (3)	0.018 (3)	0.017 (3)	0.000 (2)	0.002 (2)	−0.003 (2)
C28	0.016 (3)	0.020 (3)	0.021 (3)	0.003 (2)	0.009 (2)	0.000 (2)
C29	0.015 (3)	0.015 (3)	0.022 (3)	0.000 (2)	0.007 (2)	−0.001 (2)
C30	0.020 (3)	0.018 (3)	0.020 (3)	0.000 (2)	0.010 (2)	0.001 (2)
O3W	0.038 (3)	0.030 (3)	0.029 (2)	0.001 (2)	0.019 (2)	0.000 (2)

Geometric parameters (Å, º)

Ca—O1	2.411 (4)	Ca—O22^i	2.460 (4)
Ca—O1W	2.460 (4)	Ca—O24^ii	2.237 (5)
Ca—O2W	2.519 (4)	Ca—O4^iii	2.256 (5)
Ca—O23	2.489 (4)
I1···O24	3.210 (4)	C2···C9^xiv	3.410 (8)
I1···C23^ii	3.646 (6)	C2···C10^xiv	3.479 (9)
I1···C23^iv	3.695 (6)	C3···C10^xiv	3.378 (8)
I1···O21^v	3.672 (4)	C3···I2^iii	3.852 (6)
I2···O2^vi	3.314 (5)	C3···C7^iii	3.564 (9)
I2···C3^iii	3.852 (6)	C3···C8^xiv	3.383 (8)
I2···O4	3.230 (4)	C3···C8^iii	3.595 (8)
I1···H5^v	3.2644	C4···C10^xiv	3.599 (8)
I1···H2^vii	3.3537	C4···O4^iii	3.320 (7)
I2···H6W^viii	3.2523	C4···O1	2.945 (8)
I2···H7^ix	3.1657	C4···O22^i	3.387 (7)
S1···H2W	2.7793	C4···N1^xiv	3.391 (7)
S1···H4	2.8268	C4···C8^iii	3.520 (8)
S1···H5W	2.8486	C6···C2^iii	3.473 (9)
S1···H9^x	3.0696	C7···C3^iii	3.564 (9)
S2···H3W	2.8313	C7···C2^iii	3.352 (9)
S2···H4W^i	3.0804	C8···C3^xiv	3.383 (8)
S2···H9	2.9059	C8···C9^iii	3.510 (8)
S2···H6W^xi	2.9190	C8···C3^iii	3.595 (8)
O1···O2W	2.848 (6)	C8···C4^iii	3.520 (8)
O1···O22^i	2.832 (5)	C9···N1^xiv	3.440 (7)
O1···C4	2.945 (8)	C9···C10^iii	3.515 (8)
O1W···O23	2.949 (5)	C9···C2^xiv	3.410 (8)
O1W···O24^ii	3.180 (6)	C9···C8^iii	3.510 (8)
O1W···N2^ii	2.863 (8)	C10···C3^xiv	3.378 (8)
O1W···S1	3.295 (4)	C10···C9^iii	3.515 (8)
O1W···O3W^i	2.706 (6)	C10···C10^iii	3.270 (8)
O1W···O21	2.793 (6)	C10···C4^xiv	3.599 (8)
O1W···O22^i	2.823 (6)	C10···C2^xiv	3.479 (9)
O2···I2^xii	3.314 (5)	C22···C27^ii	3.590 (9)
O2···O3W^xi	2.878 (7)	C22···C27^iv	3.535 (9)
O2···O2W^i	2.714 (6)	C22···C26^iv	3.564 (9)
O2W···O4^iii	3.030 (6)	C23···I1^iv	3.646 (6)
O2W···N1^iii	2.892 (8)	C23···O3W^xv	3.314 (8)
O2W···O1	2.848 (6)	C23···I1^ii	3.695 (6)
O2W···O2^x	2.714 (6)	C24···O23	3.034 (8)
O2W···O3	2.882 (6)	C26···C22^ii	3.564 (9)
O2W···O23	3.069 (5)	C27···C22^ii	3.535 (9)
O2W···S2	3.270 (4)	C27···C22^iv	3.590 (9)
O3···O2W	2.882 (6)	C28···C29^iv	3.518 (8)
O3W···O1W^x	2.706 (6)	C28···C29^ii	3.555 (8)
O3W···C23^vii	3.314 (8)	C29···C28^iv	3.555 (8)
O3W···O21	2.815 (6)	C29···C28^ii	3.518 (8)
O3W···O2^xiii	2.878 (7)	C30···C30^iv	3.547 (8)
O4···O2W^iii	3.030 (6)	C30···C30^ii	3.547 (8)
O4···I2	3.230 (4)	C5···H6^iii	3.0927
O4···C4^iii	3.320 (7)	H1···O24	2.3253
O4···N1	2.681 (6)	H1···H2W^iv	2.3164
O21···O1W	2.793 (6)	H1···O1W^iv	1.9932
O21···I1^v	3.672 (4)	H1···H1W^iv	2.4760
O21···O3W	2.815 (6)	H1W···H1^ii	2.4760
O22···Ca^x	2.460 (4)	H1W···O3W^i	1.8661
O22···O1^x	2.832 (5)	H1W···H5W^i	2.2606
O22···O1W^x	2.823 (6)	H1W···H6W^i	2.3825
O22···C4^x	3.387 (7)	H2···I1^xv	3.3537
O23···O1W	2.949 (5)	H2W···S1	2.7793
O23···O2W	3.069 (5)	H2W···O21	2.0280
O23···O24^ii	3.179 (6)	H2W···H1^ii	2.3164
O23···C24	3.034 (8)	H3···O3W^xv	2.3583
O24···O23^iv	3.179 (6)	H3···H6W^xv	2.5196
O24···I1	3.210 (4)	H3W···O3	2.1585
O24···N2	2.671 (6)	H3W···O2^x	2.8174
O24···O1W^iv	3.180 (6)	H3W···S2	2.8313
O1···H3W	2.7840	H3W···H6^iii	2.2929
O1···H4^i	2.6361	H4···O1^x	2.6361
O1···H9	2.3469	H4···S1	2.8268
O1W···H1^ii	1.9932	H4···O2^x	2.9020
O2···H4^i	2.9020	H4···O23	2.4421
O2···H4W^i	1.8827	H4W···O2^x	1.8827
O2···H3W^i	2.8174	H4W···S2^x	3.0804
O2···H6W^xi	2.0486	H4W···H6^iii	2.5279
O2W···H6^iii	2.0610	H5···O21	2.4429
O3···H3W	2.1585	H5···I1^v	3.2644
O3···H10	2.4737	H5W···S1	2.8486
O3···H6W^xi	2.8776	H5W···O21	2.0048
O3W···H3^vii	2.3583	H5W···O22	2.8062
O3W···H1W^x	1.8661	H5W···H1W^x	2.2606
O4···H6	2.2721	H6···O4	2.2721
O21···H5	2.4429	H6···H3W^iii	2.2929
O21···H2W	2.0280	H6···O2W^iii	2.0610
O21···H5W	2.0048	H6···C5^iii	3.0927
O22···H5W	2.8062	H6···H4W^iii	2.5279
O22···H9^x	2.6291	H6W···H1W^x	2.3825
O22···H1W^x	2.7185	H6W···I2^viii	3.2523
O23···H2W	2.7941	H6W···O2^xiii	2.0486
O23···H9^x	2.5991	H6W···O3^xiii	2.8776
O23···H4	2.4421	H6W···S2^xiii	2.9190
O24···H1	2.3253	H6W···H3^vii	2.5196
N1···O4	2.681 (6)	H7···I2^xvi	3.1657
N1···O2W^iii	2.892 (8)	H9···S2	2.9059
N1···C9^xiv	3.440 (7)	H9···O1	2.3469
N1···C4^xiv	3.391 (7)	H9···S1^i	3.0696
N2···O24	2.671 (6)	H9···O23^i	2.5991
N2···O1W^iv	2.863 (8)	H9···O22^i	2.6291
C2···C7^iii	3.352 (9)	H10···O3	2.4737
C2···C6^iii	3.473 (9)
O1—Ca—O1W	140.85 (15)	O2W—Ca—O24^ii	95.04 (15)
O1—Ca—O2W	70.54 (14)	O2W—Ca—O4^iii	78.56 (14)
O1—Ca—O23	145.11 (14)	O22^i—Ca—O23	143.06 (13)
O1—Ca—O22^i	71.10 (13)	O23—Ca—O24^ii	84.37 (16)
O1—Ca—O24^ii	90.38 (15)	O4^iii—Ca—O23	88.76 (16)
O1—Ca—O4^iii	92.54 (15)	O22^i—Ca—O24^ii	89.84 (16)
O1W—Ca—O2W	148.57 (15)	O4^iii—Ca—O22^i	98.54 (16)
O1W—Ca—O23	73.14 (13)	O4^iii—Ca—O24^ii	171.62 (16)
O1W—Ca—O22^i	70.02 (14)	Ca—O1—S2	149.1 (3)
O1W—Ca—O24^ii	85.09 (15)	Ca^iii—O4—C8	176.7 (3)
O1W—Ca—O4^iii	97.53 (15)	Ca—O23—S1	143.2 (2)
O2W—Ca—O23	75.59 (13)	Ca^iv—O24—C28	170.8 (3)
O2W—Ca—O22^i	141.34 (14)
O1W—Ca—O1—S2	169.1 (4)	C2—N1—C10—C9	−0.3 (8)
O2W—Ca—O1—S2	−13.0 (5)	C10—N1—C2—C3	−1.4 (9)
O23—Ca—O1—S2	−27.5 (7)	C2—N1—C10—C8	178.8 (5)
O22^i—Ca—O1—S2	162.1 (6)	C30—N2—C22—C23	0.3 (9)
O24^ii—Ca—O1—S2	−108.2 (5)	C22—N2—C30—C28	−179.2 (5)
O4^iii—Ca—O1—S2	63.9 (5)	C22—N2—C30—C29	0.6 (8)
O1—Ca—O23—S1	−162.9 (4)	N1—C2—C3—C4	1.3 (9)
O1W—Ca—O23—S1	6.2 (4)	C2—C3—C4—C9	0.4 (9)
O2W—Ca—O23—S1	−177.0 (5)	C3—C4—C9—C5	178.2 (6)
O22^i—Ca—O23—S1	1.9 (6)	C3—C4—C9—C10	−2.0 (8)
O24^ii—Ca—O23—S1	−80.3 (5)	S2—C5—C6—C7	−176.9 (5)
O4^iii—Ca—O23—S1	104.5 (5)	S2—C5—C9—C4	−6.1 (8)
O4^iii—Ca—O2W—H3W	−111.63	C6—C5—C9—C4	175.8 (5)
O4^iii—Ca—O2W—H4W	112.45	C9—C5—C6—C7	1.4 (9)
O24^ii—Ca—O1W—H1W	−125.09	C6—C5—C9—C10	−4.0 (8)
O24^ii—Ca—O1W—H2W	100.39	S2—C5—C9—C10	174.1 (4)
O4^iii—Ca—O1W—H1W	62.92	C5—C6—C7—C8	2.9 (9)
O4^iii—Ca—O1W—H2W	−71.60	C5—C6—C7—I2	−179.8 (4)
O1—Ca—O2W—H3W	−14.78	I2—C7—C8—C10	178.6 (4)
O1—Ca—O2W—H4W	−150.69	C6—C7—C8—C10	−4.0 (8)
O1W—Ca—O2W—H3W	162.66	I2—C7—C8—O4	−1.4 (8)
O1—Ca—O1W—H1W	−40.55	C6—C7—C8—O4	176.0 (6)
O1—Ca—O1W—H2W	−175.07	C7—C8—C10—C9	1.2 (8)
O2W—Ca—O1W—H1W	143.28	C7—C8—C10—N1	−177.8 (5)
O2W—Ca—O1W—H2W	8.77	O4—C8—C10—C9	−178.9 (5)
O23—Ca—O1W—H1W	149.31	O4—C8—C10—N1	2.2 (8)
O23—Ca—O1W—H2W	14.80	C4—C9—C10—C8	−177.0 (5)
O22^i—Ca—O1W—H1W	−33.48	C5—C9—C10—N1	−178.2 (5)
O22^i—Ca—O1W—H2W	−167.99	C4—C9—C10—N1	1.9 (8)
O1W—Ca—O2W—H4W	26.74	C5—C9—C10—C8	2.8 (8)
O23—Ca—O2W—H3W	156.70	N2—C22—C23—C24	−0.3 (9)
O23—Ca—O2W—H4W	20.78	C22—C23—C24—C29	−0.6 (9)
O22^i—Ca—O2W—H3W	−22.22	C23—C24—C29—C30	1.5 (8)
O22^i—Ca—O2W—H4W	−158.14	C23—C24—C29—C25	−179.2 (6)
O24^ii—Ca—O2W—H3W	73.84	C29—C25—C26—C27	−0.7 (8)
O24^ii—Ca—O2W—H4W	−62.08	C26—C25—C29—C24	−177.6 (5)
O22—S1—C25—C26	103.8 (5)	S1—C25—C29—C24	1.3 (8)
O21—S1—O23—Ca	−36.2 (5)	S1—C25—C29—C30	−179.4 (4)
O22—S1—O23—Ca	−164.0 (4)	S1—C25—C26—C27	−179.6 (4)
C25—S1—O23—Ca	79.2 (5)	C26—C25—C29—C30	1.8 (8)
O23—S1—C25—C29	45.1 (5)	C25—C26—C27—C28	−1.3 (9)
O22—S1—C25—C29	−75.1 (5)	C25—C26—C27—I1	−179.4 (4)
O23—S1—C25—C26	−136.0 (4)	I1—C27—C28—C30	−179.9 (4)
O21—S1—C25—C26	−16.2 (5)	I1—C27—C28—O24	−0.3 (8)
O21—S1—C25—C29	164.9 (5)	C26—C27—C28—O24	−178.5 (5)
O2—S2—C5—C9	87.1 (5)	C26—C27—C28—C30	1.9 (8)
O3—S2—C5—C9	−152.8 (5)	O24—C28—C30—N2	−0.5 (8)
C5—S2—O1—Ca	−72.6 (6)	C27—C28—C30—C29	−0.7 (8)
O3—S2—C5—C6	25.4 (5)	O24—C28—C30—C29	179.7 (5)
O1—S2—C5—C9	−31.8 (5)	C27—C28—C30—N2	179.1 (5)
O2—S2—O1—Ca	171.5 (5)	C24—C29—C30—N2	−1.5 (8)
O3—S2—O1—Ca	43.6 (6)	C24—C29—C30—C28	178.3 (5)
O1—S2—C5—C6	146.4 (4)	C25—C29—C30—N2	179.1 (5)
O2—S2—C5—C6	−94.7 (5)	C25—C29—C30—C28	−1.1 (8)

Symmetry codes: (i) x, y−1, z; (ii) −x+1, y−1/2, −z+3/2; (iii) −x+2, −y+1, −z+2; (iv) −x+1, y+1/2, −z+3/2; (v) −x+1, −y+2, −z+1; (vi) −x+2, y+1/2, −z+5/2; (vii) x, −y+5/2, z−1/2; (viii) −x+2, −y+2, −z+2; (ix) x, −y+1/2, z+1/2; (x) x, y+1, z; (xi) x, −y+3/2, z+1/2; (xii) −x+2, y−1/2, −z+5/2; (xiii) x, −y+3/2, z−1/2; (xiv) −x+2, −y, −z+2; (xv) x, −y+5/2, z+1/2; (xvi) x, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···O24	0.90	2.33	2.671 (6)	103
N2—H1···O1W^iv	0.90	1.99	2.863 (8)	162
O1W—H1W···O3W^i	0.85	1.87	2.706 (6)	169
O1W—H2W···O21	0.85	2.03	2.793 (6)	149
O2W—H3W···O3	0.85	2.16	2.882 (6)	143
O2W—H4W···O2^x	0.85	1.88	2.714 (6)	166
O3W—H5W···O21	0.85	2.00	2.815 (6)	159
N1—H6···O4	0.90	2.27	2.681 (6)	107
N1—H6···O2W^iii	0.90	2.06	2.892 (8)	153
O3W—H6W···O2^xiii	0.85	2.05	2.878 (7)	165
C23—H3···O3W^xv	0.96	2.36	3.314 (8)	174
C24—H4···O23	0.96	2.44	3.034 (8)	120
C26—H5···O21	0.96	2.44	2.857 (8)	106
C4—H9···O1	0.96	2.35	2.945 (8)	120
C4—H9···O23^i	0.96	2.60	3.457 (7)	149
C6—H10···O3	0.96	2.47	2.868 (8)	104

Symmetry codes: (i) x, y−1, z; (iii) −x+2, −y+1, −z+2; (iv) −x+1, y+1/2, −z+3/2; (x) x, y+1, z; (xiii) x, −y+3/2, z−1/2; (xv) x, −y+5/2, z+1/2.