Tetra-kis(2,4,6-triamino-1,3,5-triazin-1-ium) tris-(pyridine-2,6-dicarboxyl-ato)calcate(II) hexa-hydrate.

The title compound, (C(3)H(7)N(6))(4)[Ca(C(7)H(3)NO(4))(3)]·6H(2)O or (tataH)(4)[Ca(pydc)(3)]·6H(2)O (where tata is 2,4,6-triamino-1,3,5-triazine and pydcH(2) is pyridine-2,6-dicarboxylic acid), was obtained by reaction of Ca(NO(3))(2)·4H(2)O with the proton-transfer compound (tataH)(2)(pydc) in aqueous solution. The [Ca(pydc)(3)](4-) anion has twofold crystallographic symmetry. It is a nine-coordinate Ca(II) complex with a distorted tricapped trigonal-prismatic coordination geometry. The structure also contains four tataH(+) cations and six uncoordinated water mol-ecules. There are extensive O-H⋯O, O-H⋯N, N-H⋯O, N-H⋯N and C-H⋯O hydrogen bonds in the crystal structure.

Related literature

For related literature, see: Aghabozorg et al. (2006 ▶); Aghabozorg, Attar Gharamaleki et al. (2008 ▶); Aghabozorg, Manteghi & Sheshmani (2008 ▶); Aghajani et al. (2006 ▶); Sharif et al. (2007 ▶).

Experimental

Crystal data

(C3H7N6)4[Ca(C7H3NO4)3]·6H2O

M = 1152.07

Monoclinic,

a = 17.9605 (15) Å

b = 10.1672 (9) Å

c = 25.922 (2) Å

β = 94.467 (2)°

V = 4719.1 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 100 (2) K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.928, T max = 0.954

16983 measured reflections

6215 independent reflections

4412 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.127

S = 1.09

6215 reflections

365 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.77 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808022873/om2249sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022873/om2249Isup2.hkl

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

(C3H7N6)4[Ca(C7H3N1O4)3]·6H2O	F000 = 2400
Mr = 1152.07	Dx = 1.622 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 935 reflections
a = 17.9605 (15) Å	θ = 3–29º
b = 10.1672 (9) Å	µ = 0.24 mm−1
c = 25.922 (2) Å	T = 100 (2) K
β = 94.467 (2)º	Prism, colourless
V = 4719.1 (7) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Bruker SMART APEXII diffractometer	6215 independent reflections
Radiation source: fine-focus sealed tube	4412 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.031
T = 100(2) K	θmax = 29.0º
ω scans	θmin = 1.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −19→24
Tmin = 0.928, Tmax = 0.954	k = −13→13
16983 measured reflections	l = −35→35

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051	H-atom parameters constrained
wR(F2) = 0.127	w = 1/[σ2(Fo2) + (0.0392P)2 + 1P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
6215 reflections	Δρmax = 0.51 e Å−3
365 parameters	Δρmin = −0.77 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
Ca1	0.0000	0.32225 (5)	0.2500	0.01468 (13)
C1	0.17008 (12)	0.2206 (2)	0.21823 (8)	0.0189 (4)
N1	0.12161 (10)	0.19798 (16)	0.25401 (6)	0.0167 (3)
O1	0.08882 (8)	0.38891 (14)	0.18496 (5)	0.0198 (3)
O1W	0.25538 (11)	0.3625 (2)	−0.08194 (7)	0.0511 (6)
H1WB	0.2800	0.3196	−0.1025	0.061*
H1WA	0.2150	0.3792	−0.0992	0.061*
O2W	0.20543 (11)	0.3177 (2)	0.38198 (7)	0.0464 (5)
H2WB	0.2093	0.3575	0.4105	0.056*
H2WA	0.1704	0.3502	0.3627	0.056*
O2	0.18167 (9)	0.32683 (15)	0.13789 (6)	0.0225 (3)
N2	0.0000	0.5723 (2)	0.2500	0.0160 (5)
C2	0.23993 (13)	0.1634 (3)	0.21999 (9)	0.0291 (5)
H2A	0.2733	0.1824	0.1943	0.035*
O3W	0.16530 (16)	0.8783 (3)	0.17830 (10)	0.0743 (8)
H3WB	0.2094	0.8677	0.1704	0.089*
H3WA	0.1367	0.9132	0.1550	0.089*
N3	0.16153 (10)	0.53273 (18)	0.07458 (7)	0.0222 (4)
H3N	0.1666	0.4663	0.0963	0.027*
O3	0.02261 (8)	0.15716 (14)	0.32346 (5)	0.0203 (3)
C3	0.26030 (14)	0.0777 (3)	0.26017 (9)	0.0345 (6)
H3A	0.3079	0.0366	0.2624	0.041*
O4	0.10324 (9)	0.02965 (15)	0.37134 (6)	0.0252 (3)
C4	0.21035 (14)	0.0525 (2)	0.29714 (9)	0.0292 (5)
H4A	0.2230	−0.0063	0.3249	0.035*
N4	0.18475 (10)	0.62366 (18)	−0.00573 (7)	0.0217 (4)
O5	0.08073 (9)	0.43271 (14)	0.32086 (6)	0.0220 (3)
C5	0.14127 (12)	0.1153 (2)	0.29278 (8)	0.0183 (4)
N5	0.12433 (10)	0.75024 (17)	0.05810 (7)	0.0207 (4)
N6	0.22996 (11)	0.41835 (19)	0.01860 (8)	0.0275 (4)
H6NA	0.2338	0.3554	0.0419	0.033*
H6NB	0.2477	0.4118	−0.0120	0.033*
O6	0.11801 (9)	0.61386 (15)	0.36402 (6)	0.0236 (3)
C6	0.14421 (12)	0.3194 (2)	0.17714 (7)	0.0174 (4)
N7	0.13887 (10)	0.83102 (18)	−0.02277 (7)	0.0224 (4)
H7NA	0.1188	0.9049	−0.0129	0.027*
H7NB	0.1526	0.8246	−0.0545	0.027*
C7	0.08494 (12)	0.09839 (19)	0.33279 (8)	0.0171 (4)
N8	0.09931 (11)	0.64715 (19)	0.13431 (7)	0.0257 (4)
H8NA	0.0972	0.5743	0.1525	0.031*
H8NB	0.0923	0.7219	0.1503	0.031*
C8	0.04098 (11)	0.6393 (2)	0.28661 (8)	0.0175 (4)
N9	−0.02526 (10)	0.21627 (17)	0.41916 (6)	0.0189 (4)
H9NA	−0.0085	0.2124	0.3882	0.023*
C9	0.04259 (14)	0.7762 (2)	0.28768 (9)	0.0250 (5)
H9A	0.0724	0.8215	0.3138	0.030*
C10	0.0000	0.8452 (3)	0.2500	0.0301 (8)
H10A	0.0000	0.9386	0.2500	0.036*
N10	−0.03939 (10)	0.32331 (17)	0.49808 (6)	0.0179 (4)
C11	0.08390 (11)	0.5555 (2)	0.32701 (8)	0.0170 (4)
N11	−0.07504 (10)	0.09514 (17)	0.48552 (7)	0.0187 (4)
N12	0.01468 (10)	0.42995 (18)	0.43181 (7)	0.0219 (4)
H11A	0.0226	0.4986	0.4522	0.041 (8)*
H11B	0.0304	0.4273	0.4005	0.033 (7)*
C12	0.15006 (12)	0.7326 (2)	0.01068 (8)	0.0199 (4)
N13	−0.08510 (11)	0.19908 (18)	0.56239 (7)	0.0230 (4)
H13A	−0.0983	0.1240	0.5759	0.039 (8)*
H13B	−0.0842	0.2683	0.5828	0.029 (7)*
C13	0.12875 (12)	0.6464 (2)	0.08866 (8)	0.0206 (4)
N14	−0.06375 (11)	0.00349 (19)	0.40544 (7)	0.0273 (4)
H14A	−0.0459	0.0126	0.3750	0.033 (7)*
H14B	−0.0830	−0.0706	0.4158	0.036 (8)*
C14	0.19208 (12)	0.5258 (2)	0.02825 (8)	0.0217 (4)
C15	−0.01687 (11)	0.3235 (2)	0.45053 (8)	0.0171 (4)
C16	−0.06599 (12)	0.2060 (2)	0.51433 (8)	0.0183 (4)
C17	−0.05485 (11)	0.1040 (2)	0.43758 (8)	0.0188 (4)

	U11	U22	U33	U12	U13	U23
Ca1	0.0160 (3)	0.0136 (3)	0.0145 (3)	0.000	0.0015 (2)	0.000
C1	0.0193 (11)	0.0216 (10)	0.0160 (9)	0.0004 (8)	0.0023 (8)	0.0019 (8)
N1	0.0178 (9)	0.0173 (8)	0.0150 (8)	−0.0001 (7)	0.0020 (6)	−0.0004 (6)
O1	0.0198 (8)	0.0186 (7)	0.0215 (7)	0.0008 (6)	0.0044 (6)	0.0036 (6)
O1W	0.0303 (10)	0.0852 (16)	0.0357 (10)	0.0236 (10)	−0.0111 (8)	−0.0261 (10)
O2W	0.0510 (12)	0.0472 (12)	0.0378 (10)	0.0222 (10)	−0.0160 (9)	−0.0154 (9)
O2	0.0240 (8)	0.0243 (8)	0.0200 (7)	0.0016 (6)	0.0077 (6)	0.0054 (6)
N2	0.0160 (12)	0.0156 (11)	0.0168 (11)	0.000	0.0044 (9)	0.000
C2	0.0240 (12)	0.0416 (14)	0.0227 (11)	0.0080 (11)	0.0074 (9)	0.0077 (10)
O3W	0.089 (2)	0.0615 (16)	0.0691 (17)	0.0005 (15)	−0.0175 (14)	−0.0047 (13)
N3	0.0229 (10)	0.0190 (9)	0.0250 (9)	0.0023 (7)	0.0041 (8)	0.0065 (7)
O3	0.0202 (8)	0.0223 (8)	0.0187 (7)	0.0012 (6)	0.0037 (6)	0.0027 (6)
C3	0.0242 (13)	0.0500 (16)	0.0300 (13)	0.0167 (11)	0.0075 (10)	0.0120 (11)
O4	0.0322 (9)	0.0242 (8)	0.0197 (7)	0.0030 (7)	0.0047 (6)	0.0077 (6)
C4	0.0303 (13)	0.0347 (13)	0.0227 (11)	0.0120 (11)	0.0038 (9)	0.0097 (10)
N4	0.0190 (9)	0.0227 (9)	0.0230 (9)	0.0009 (7)	0.0003 (7)	0.0035 (7)
O5	0.0249 (8)	0.0161 (7)	0.0238 (8)	−0.0007 (6)	−0.0048 (6)	−0.0004 (6)
C5	0.0209 (11)	0.0182 (10)	0.0160 (9)	0.0029 (8)	0.0022 (8)	0.0008 (7)
N5	0.0205 (9)	0.0192 (9)	0.0220 (9)	−0.0017 (7)	0.0004 (7)	0.0015 (7)
N6	0.0297 (11)	0.0248 (10)	0.0290 (10)	0.0063 (8)	0.0080 (8)	0.0063 (8)
O6	0.0250 (8)	0.0246 (8)	0.0205 (7)	−0.0011 (7)	−0.0031 (6)	−0.0052 (6)
C6	0.0188 (10)	0.0183 (10)	0.0149 (9)	−0.0030 (8)	0.0006 (8)	0.0002 (7)
N7	0.0233 (10)	0.0222 (9)	0.0217 (9)	0.0012 (8)	0.0006 (7)	0.0037 (7)
C7	0.0231 (11)	0.0117 (9)	0.0167 (9)	−0.0021 (8)	0.0029 (8)	−0.0013 (7)
N8	0.0339 (11)	0.0198 (9)	0.0241 (9)	0.0005 (8)	0.0065 (8)	0.0028 (7)
C8	0.0183 (10)	0.0171 (9)	0.0178 (9)	−0.0006 (8)	0.0055 (8)	−0.0011 (7)
N9	0.0219 (9)	0.0207 (9)	0.0147 (8)	0.0016 (7)	0.0050 (7)	0.0009 (7)
C9	0.0322 (13)	0.0194 (10)	0.0228 (11)	−0.0025 (9)	−0.0019 (9)	−0.0030 (8)
C10	0.044 (2)	0.0179 (15)	0.0273 (17)	0.000	−0.0032 (15)	0.000
N10	0.0215 (9)	0.0158 (8)	0.0167 (8)	0.0008 (7)	0.0032 (7)	0.0012 (6)
C11	0.0146 (10)	0.0199 (10)	0.0168 (9)	−0.0012 (8)	0.0034 (7)	−0.0010 (7)
N11	0.0197 (9)	0.0173 (8)	0.0193 (8)	−0.0011 (7)	0.0038 (7)	−0.0011 (7)
N12	0.0249 (10)	0.0214 (9)	0.0200 (9)	−0.0006 (8)	0.0068 (7)	0.0025 (7)
C12	0.0144 (10)	0.0228 (10)	0.0217 (10)	−0.0031 (8)	−0.0035 (8)	0.0027 (8)
N13	0.0356 (11)	0.0160 (9)	0.0182 (8)	−0.0043 (8)	0.0071 (8)	−0.0012 (7)
C13	0.0185 (10)	0.0201 (10)	0.0227 (10)	−0.0027 (8)	−0.0004 (8)	0.0012 (8)
N14	0.0353 (11)	0.0258 (10)	0.0221 (9)	−0.0079 (9)	0.0106 (8)	−0.0068 (8)
C14	0.0152 (10)	0.0234 (11)	0.0265 (11)	−0.0008 (8)	0.0009 (8)	0.0033 (8)
C15	0.0150 (10)	0.0172 (9)	0.0189 (9)	0.0024 (8)	0.0004 (7)	0.0021 (8)
C16	0.0170 (10)	0.0183 (10)	0.0197 (10)	0.0016 (8)	0.0014 (8)	0.0009 (8)
C17	0.0155 (10)	0.0206 (10)	0.0204 (10)	0.0015 (8)	0.0020 (8)	−0.0013 (8)

Ca1—O1	2.5031 (14)	O5—C11	1.259 (2)
Ca1—O1i	2.5032 (14)	C5—C7	1.514 (3)
Ca1—O5i	2.5145 (15)	N5—C13	1.319 (3)
Ca1—O5	2.5145 (15)	N5—C12	1.358 (3)
Ca1—N1i	2.5184 (18)	N6—C14	1.321 (3)
Ca1—N1	2.5184 (18)	N6—H6NA	0.8800
Ca1—N2	2.542 (2)	N6—H6NB	0.8798
Ca1—O3i	2.5472 (15)	O6—C11	1.248 (2)
Ca1—O3	2.5472 (15)	N7—C12	1.329 (3)
C1—N1	1.340 (3)	N7—H7NA	0.8800
C1—C2	1.380 (3)	N7—H7NB	0.8800
C1—C6	1.511 (3)	N8—C13	1.333 (3)
N1—C5	1.337 (3)	N8—H8NA	0.8800
O1—C6	1.250 (2)	N8—H8NB	0.8800
O1W—H1WB	0.8400	C8—C9	1.393 (3)
O1W—H1WA	0.8400	C8—C11	1.514 (3)
O2W—H2WB	0.8400	N9—C15	1.362 (3)
O2W—H2WA	0.8400	N9—C17	1.361 (3)
O2—C6	1.265 (2)	N9—H9NA	0.8800
N2—C8i	1.340 (2)	C9—C10	1.384 (3)
N2—C8	1.340 (2)	C9—H9A	0.9500
C2—C3	1.385 (3)	C10—C9i	1.384 (3)
C2—H2A	0.9500	C10—H10A	0.9500
O3W—H3WB	0.8400	N10—C15	1.327 (3)
O3W—H3WA	0.8401	N10—C16	1.363 (3)
N3—C13	1.360 (3)	N11—C17	1.324 (3)
N3—C14	1.360 (3)	N11—C16	1.355 (3)
N3—H3N	0.8800	N12—C15	1.330 (3)
O3—C7	1.275 (3)	N12—H11A	0.8801
C3—C4	1.386 (3)	N12—H11B	0.8799
C3—H3A	0.9500	N13—C16	1.319 (3)
O4—C7	1.243 (2)	N13—H13A	0.8800
C4—C5	1.392 (3)	N13—H13B	0.8799
C4—H4A	0.9500	N14—C17	1.320 (3)
N4—C14	1.329 (3)	N14—H14A	0.8800
N4—C12	1.356 (3)	N14—H14B	0.8800
O1—Ca1—O1i	148.58 (7)	N1—C5—C4	122.08 (19)
O1—Ca1—O5i	75.43 (5)	N1—C5—C7	115.77 (18)
O1i—Ca1—O5i	90.55 (5)	C4—C5—C7	122.11 (19)
O1—Ca1—O5	90.55 (5)	C13—N5—C12	115.43 (19)
O1i—Ca1—O5	75.43 (5)	C14—N6—H6NA	119.0
O5i—Ca1—O5	126.94 (7)	C14—N6—H6NB	117.5
O1—Ca1—N1i	134.76 (5)	H6NA—N6—H6NB	123.4
O1i—Ca1—N1i	64.37 (5)	O1—C6—O2	125.19 (19)
O5i—Ca1—N1i	75.23 (5)	O1—C6—C1	117.84 (17)
O5—Ca1—N1i	134.68 (5)	O2—C6—C1	116.96 (18)
O1—Ca1—N1	64.37 (5)	C12—N7—H7NA	119.8
O1i—Ca1—N1	134.76 (5)	C12—N7—H7NB	121.1
O5i—Ca1—N1	134.68 (5)	H7NA—N7—H7NB	119.1
O5—Ca1—N1	75.23 (5)	O4—C7—O3	126.11 (19)
N1i—Ca1—N1	119.78 (8)	O4—C7—C5	117.75 (19)
O1—Ca1—N2	74.29 (4)	O3—C7—C5	116.14 (17)
O1i—Ca1—N2	74.29 (4)	C13—N8—H8NA	120.4
O5i—Ca1—N2	63.47 (4)	C13—N8—H8NB	120.4
O5—Ca1—N2	63.47 (4)	H8NA—N8—H8NB	117.4
N1i—Ca1—N2	120.11 (4)	N2—C8—C9	122.1 (2)
N1—Ca1—N2	120.11 (4)	N2—C8—C11	115.19 (18)
O1—Ca1—O3i	75.39 (5)	C9—C8—C11	122.70 (19)
O1i—Ca1—O3i	127.53 (5)	C15—N9—C17	119.35 (17)
O5i—Ca1—O3i	72.48 (5)	C15—N9—H9NA	123.4
O5—Ca1—O3i	152.84 (5)	C17—N9—H9NA	117.0
N1i—Ca1—O3i	63.34 (5)	C10—C9—C8	118.9 (2)
N1—Ca1—O3i	77.73 (5)	C10—C9—H9A	120.6
N2—Ca1—O3i	131.22 (3)	C8—C9—H9A	120.6
O1—Ca1—O3	127.53 (5)	C9i—C10—C9	119.1 (3)
O1i—Ca1—O3	75.39 (5)	C9i—C10—H10A	120.5
O5i—Ca1—O3	152.84 (5)	C9—C10—H10A	120.5
O5—Ca1—O3	72.48 (5)	C15—N10—C16	115.35 (18)
N1i—Ca1—O3	77.73 (5)	O6—C11—O5	125.73 (19)
N1—Ca1—O3	63.34 (5)	O6—C11—C8	117.19 (18)
N2—Ca1—O3	131.22 (3)	O5—C11—C8	117.06 (18)
O3i—Ca1—O3	97.56 (7)	C17—N11—C16	115.51 (18)
N1—C1—C2	122.86 (19)	C15—N12—H11A	118.7
N1—C1—C6	114.91 (18)	C15—N12—H11B	119.2
C2—C1—C6	122.16 (19)	H11A—N12—H11B	121.9
C5—N1—C1	118.70 (18)	N7—C12—N4	117.41 (19)
C5—N1—Ca1	121.61 (13)	N7—C12—N5	116.5 (2)
C1—N1—Ca1	119.56 (13)	N4—C12—N5	126.05 (19)
C6—O1—Ca1	120.86 (12)	C16—N13—H13A	121.4
H1WB—O1W—H1WA	104.1	C16—N13—H13B	122.1
H2WB—O2W—H2WA	109.9	H13A—N13—H13B	116.5
C8i—N2—C8	118.9 (2)	N5—C13—N8	121.3 (2)
C8i—N2—Ca1	120.53 (12)	N5—C13—N3	121.8 (2)
C8—N2—Ca1	120.53 (12)	N8—C13—N3	116.96 (19)
C3—C2—C1	118.4 (2)	C17—N14—H14A	116.7
C3—C2—H2A	120.8	C17—N14—H14B	120.1
C1—C2—H2A	120.8	H14A—N14—H14B	123.0
H3WB—O3W—H3WA	114.4	N6—C14—N4	121.3 (2)
C13—N3—C14	119.60 (18)	N6—C14—N3	117.3 (2)
C13—N3—H3N	120.4	N4—C14—N3	121.4 (2)
C14—N3—H3N	119.8	N10—C15—N12	120.64 (19)
C7—O3—Ca1	122.48 (12)	N10—C15—N9	121.73 (18)
C2—C3—C4	119.2 (2)	N12—C15—N9	117.63 (18)
C2—C3—H3A	120.4	N13—C16—N11	116.54 (19)
C4—C3—H3A	120.4	N13—C16—N10	117.51 (19)
C3—C4—C5	118.7 (2)	N11—C16—N10	125.96 (18)
C3—C4—H4A	120.7	N14—C17—N11	120.7 (2)
C5—C4—H4A	120.7	N14—C17—N9	117.33 (19)
C14—N4—C12	115.36 (18)	N11—C17—N9	121.95 (19)
C11—O5—Ca1	123.58 (13)
C2—C1—N1—C5	−0.8 (3)	N1—Ca1—O5—C11	138.44 (17)
C6—C1—N1—C5	−177.72 (18)	N2—Ca1—O5—C11	3.08 (14)
C2—C1—N1—Ca1	175.25 (18)	O3i—Ca1—O5—C11	132.90 (16)
C6—C1—N1—Ca1	−1.6 (2)	O3—Ca1—O5—C11	−155.35 (17)
O1—Ca1—N1—C5	171.11 (17)	C1—N1—C5—C4	0.2 (3)
O1i—Ca1—N1—C5	22.09 (19)	Ca1—N1—C5—C4	−175.81 (17)
O5i—Ca1—N1—C5	−158.97 (14)	C1—N1—C5—C7	177.82 (18)
O5—Ca1—N1—C5	73.20 (15)	Ca1—N1—C5—C7	1.8 (2)
N1i—Ca1—N1—C5	−60.19 (14)	C3—C4—C5—N1	0.4 (4)
N2—Ca1—N1—C5	119.81 (14)	C3—C4—C5—C7	−177.1 (2)
O3i—Ca1—N1—C5	−109.38 (16)	Ca1—O1—C6—O2	162.52 (16)
O3—Ca1—N1—C5	−4.32 (14)	Ca1—O1—C6—C1	−19.1 (2)
O1—Ca1—N1—C1	−4.88 (14)	N1—C1—C6—O1	13.5 (3)
O1i—Ca1—N1—C1	−153.89 (14)	C2—C1—C6—O1	−163.4 (2)
O5i—Ca1—N1—C1	25.05 (18)	N1—C1—C6—O2	−167.97 (18)
O5—Ca1—N1—C1	−102.78 (15)	C2—C1—C6—O2	15.1 (3)
N1i—Ca1—N1—C1	123.83 (16)	Ca1—O3—C7—O4	170.52 (16)
N2—Ca1—N1—C1	−56.17 (16)	Ca1—O3—C7—C5	−9.4 (2)
O3i—Ca1—N1—C1	74.64 (15)	N1—C5—C7—O4	−175.02 (18)
O3—Ca1—N1—C1	179.70 (17)	C4—C5—C7—O4	2.6 (3)
O1i—Ca1—O1—C6	148.51 (15)	N1—C5—C7—O3	4.9 (3)
O5i—Ca1—O1—C6	−145.46 (15)	C4—C5—C7—O3	−177.5 (2)
O5—Ca1—O1—C6	86.33 (15)	C8i—N2—C8—C9	−0.29 (15)
N1i—Ca1—O1—C6	−94.42 (16)	Ca1—N2—C8—C9	179.71 (15)
N1—Ca1—O1—C6	13.04 (14)	C8i—N2—C8—C11	178.57 (19)
N2—Ca1—O1—C6	148.51 (15)	Ca1—N2—C8—C11	−1.43 (19)
O3i—Ca1—O1—C6	−70.16 (15)	N2—C8—C9—C10	0.6 (3)
O3—Ca1—O1—C6	18.19 (17)	C11—C8—C9—C10	−178.21 (17)
O1—Ca1—N2—C8i	80.76 (10)	C8—C9—C10—C9i	−0.27 (14)
O1i—Ca1—N2—C8i	−99.24 (10)	Ca1—O5—C11—O6	173.48 (15)
O5i—Ca1—N2—C8i	−0.53 (11)	Ca1—O5—C11—C8	−5.0 (2)
O5—Ca1—N2—C8i	179.47 (11)	N2—C8—C11—O6	−174.49 (16)
N1i—Ca1—N2—C8i	−52.29 (11)	C9—C8—C11—O6	4.4 (3)
N1—Ca1—N2—C8i	127.71 (11)	N2—C8—C11—O5	4.1 (3)
O3i—Ca1—N2—C8i	27.26 (11)	C9—C8—C11—O5	−177.1 (2)
O3—Ca1—N2—C8i	−152.74 (11)	C14—N4—C12—N7	−177.40 (19)
O1—Ca1—N2—C8	−99.24 (10)	C14—N4—C12—N5	1.4 (3)
O1i—Ca1—N2—C8	80.76 (10)	C13—N5—C12—N7	172.95 (19)
O5i—Ca1—N2—C8	179.47 (11)	C13—N5—C12—N4	−5.9 (3)
O5—Ca1—N2—C8	−0.53 (11)	C12—N5—C13—N8	−173.9 (2)
N1i—Ca1—N2—C8	127.71 (11)	C12—N5—C13—N3	4.3 (3)
N1—Ca1—N2—C8	−52.29 (11)	C14—N3—C13—N5	1.3 (3)
O3i—Ca1—N2—C8	−152.74 (11)	C14—N3—C13—N8	179.6 (2)
O3—Ca1—N2—C8	27.26 (11)	C12—N4—C14—N6	−174.6 (2)
N1—C1—C2—C3	0.8 (4)	C12—N4—C14—N3	4.7 (3)
C6—C1—C2—C3	177.5 (2)	C13—N3—C14—N6	173.2 (2)
O1—Ca1—O3—C7	2.23 (17)	C13—N3—C14—N4	−6.2 (3)
O1i—Ca1—O3—C7	−153.52 (15)	C16—N10—C15—N12	−175.54 (19)
O5i—Ca1—O3—C7	145.59 (14)	C16—N10—C15—N9	4.7 (3)
O5—Ca1—O3—C7	−74.48 (15)	C17—N9—C15—N10	−2.6 (3)
N1i—Ca1—O3—C7	140.11 (15)	C17—N9—C15—N12	177.67 (18)
N1—Ca1—O3—C7	7.43 (14)	C17—N11—C16—N13	−179.39 (19)
N2—Ca1—O3—C7	−100.42 (14)	C17—N11—C16—N10	0.9 (3)
O3i—Ca1—O3—C7	79.58 (14)	C15—N10—C16—N13	176.27 (19)
C1—C2—C3—C4	−0.2 (4)	C15—N10—C16—N11	−4.0 (3)
C2—C3—C4—C5	−0.4 (4)	C16—N11—C17—N14	−177.5 (2)
O1—Ca1—O5—C11	75.17 (16)	C16—N11—C17—N9	1.6 (3)
O1i—Ca1—O5—C11	−76.38 (16)	C15—N9—C17—N14	178.31 (19)
O5i—Ca1—O5—C11	3.08 (14)	C15—N9—C17—N11	−0.8 (3)
N1i—Ca1—O5—C11	−104.08 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WB···O2ii	0.84	1.91	2.710 (3)	160
O1W—H1WA···O6iii	0.84	1.92	2.751 (3)	170
O2W—H2WB···N4iv	0.84	2.26	3.022 (3)	151
N3—H3N···O2	0.88	1.79	2.667 (2)	176
O2W—H2WA···O5	0.84	2.05	2.888 (3)	175
O3W—H3WB···O2Wv	0.84	2.18	2.963 (3)	154
O3W—H3WA···N14vi	0.84	2.17	3.007 (3)	180
N6—H6NA···O1Wii	0.88	2.45	3.294 (3)	162
N6—H6NB···O1W	0.88	1.90	2.740 (3)	160
N7—H7NA···N11vi	0.88	2.22	3.103 (3)	176
N7—H7NB···O2Wiii	0.88	2.44	3.205 (3)	146
N7—H7NB···O4iii	0.88	2.53	3.111 (2)	124
N8—H8NA···O1	0.88	2.07	2.948 (2)	172
N12—H11A···N10vii	0.88	2.23	3.109 (2)	178
N12—H11B···O5	0.88	2.32	3.196 (2)	175
N8—H8NB···O3W	0.88	2.15	2.832 (4)	134
N9—H9NA···O3	0.88	1.89	2.754 (2)	165
N13—H13A···O4viii	0.88	2.08	2.925 (2)	160
N13—H13B···O6vii	0.88	1.96	2.790 (2)	157
N14—H14A···O3	0.88	2.39	3.143 (2)	144
N14—H14B···N5ix	0.88	2.10	2.978 (3)	178
C4—H4A···O2x	0.95	2.55	3.370 (3)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WB⋯O2i	0.84	1.91	2.710 (3)	160
O1W—H1WA⋯O6ii	0.84	1.92	2.751 (3)	170
O2W—H2WB⋯N4iii	0.84	2.26	3.022 (3)	151
N3—H3N⋯O2	0.88	1.79	2.667 (2)	176
O2W—H2WA⋯O5	0.84	2.05	2.888 (3)	175
O3W—H3WB⋯O2Wiv	0.84	2.18	2.963 (3)	154
O3W—H3WA⋯N14v	0.84	2.17	3.007 (3)	180
N6—H6NA⋯O1Wi	0.88	2.45	3.294 (3)	162
N6—H6NB⋯O1W	0.88	1.90	2.740 (3)	160
N7—H7NA⋯N11v	0.88	2.22	3.103 (3)	176
N7—H7NB⋯O2Wii	0.88	2.44	3.205 (3)	146
N7—H7NB⋯O4ii	0.88	2.53	3.111 (2)	124
N8—H8NA⋯O1	0.88	2.07	2.948 (2)	172
N12—H11A⋯N10vi	0.88	2.23	3.109 (2)	178
N12—H11B⋯O5	0.88	2.32	3.196 (2)	175
N8—H8NB⋯O3W	0.88	2.15	2.832 (4)	134
N9—H9NA⋯O3	0.88	1.89	2.754 (2)	165
N13—H13A⋯O4vii	0.88	2.08	2.925 (2)	160
N13—H13B⋯O6vi	0.88	1.96	2.790 (2)	157
N14—H14A⋯O3	0.88	2.39	3.143 (2)	144
N14—H14B⋯N5viii	0.88	2.10	2.978 (3)	178
C4—H4A⋯O2ix	0.95	2.55	3.370 (3)	145

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) ; (ix) .