Tetra-aqua-hexa-kis(μ(2)-quinoline-4-carboxyl-ato)diyttrium(III) dihydrate.

In the title centrosymmetric binuclear complex, [Y(2)(C(10)H(6)NO(2))(6)(H(2)O)(4)]·2H(2)O, each Y(III) atom is nine-coordin-ated by nine O atoms from five ligands and two water mol-ecules in a slightly distorted monocapped square-anti-prismatic coordination environment. The Y(III) atoms are separated by a distance of 4.0363 (9) Å. The ligands coordinate in three different modes: chelating, bridging and a mixed chelating bridging mode. In the crystal structure, the binuclear complexes are linked by O-H⋯O and O-H⋯N hydrogen bonds, forming a three-dimensional network.

Related literature

For transition metal complexes of 4-quinoline­carboxylic acid, see: Bu et al. (2005 ▶); Chen et al. (2002 ▶); Morsy & Vratislav (2006 ▶).

Experimental

Crystal data

[Y2(C10H6NO2)6(H2O)4]·2H2O

M = 1318.86

Monoclinic,

a = 11.623 (2) Å

b = 16.361 (3) Å

c = 15.312 (3) Å

β = 106.03 (3)°

V = 2798.7 (10) Å3

Z = 2

Mo Kα radiation

μ = 2.15 mm−1

T = 293 (2) K

0.30 × 0.28 × 0.26 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.565, T max = 0.605 (expected range = 0.535–0.573)

9525 measured reflections

4898 independent reflections

3615 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.073

S = 0.91

4898 reflections

412 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.30 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808039421/su2081sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039421/su2081Isup2.hkl

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

[Y2(C10H6NO2)6(H2O)4]·2H2O	F000 = 1344
Mr = 1318.86	Dx = 1.565 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6629 reflections
a = 11.623 (2) Å	θ = 3.0–27.5º
b = 16.361 (3) Å	µ = 2.15 mm−1
c = 15.312 (3) Å	T = 293 (2) K
β = 106.03 (3)º	Block, colorless
V = 2798.7 (10) Å3	0.30 × 0.28 × 0.26 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	4898 independent reflections
Radiation source: fine-focus sealed tube	3615 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.031
T = 293(2) K	θmax = 25.0º
φ and ω scans	θmin = 3.0º
Absorption correction: multi-scan(SADABS; Bruker, 1998)	h = −13→13
Tmin = 0.565, Tmax = 0.605	k = −19→19
9525 measured reflections	l = −18→18

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)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.073	w = 1/[σ2(Fo2) + (0.0401P)2] where P = (Fo2 + 2Fc2)/3
S = 0.91	(Δ/σ)max = 0.003
4898 reflections	Δρmax = 0.38 e Å−3
412 parameters	Δρmin = −0.30 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su'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

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
Y1	0.33612 (2)	0.97169 (1)	1.01215 (2)	0.0277 (1)
O1	0.3073 (2)	0.93621 (12)	1.15662 (15)	0.0601 (9)
O1W	0.1551 (2)	0.91430 (16)	0.92842 (18)	0.0555 (9)
O2	0.32722 (19)	0.83332 (12)	1.07294 (14)	0.0534 (8)
O2W	0.1754 (2)	1.05108 (15)	1.0333 (2)	0.0506 (9)
O3	0.58136 (16)	0.91289 (11)	0.90536 (13)	0.0421 (7)
O4	0.39176 (15)	0.88949 (10)	0.90683 (13)	0.0382 (6)
O5	0.27258 (18)	1.06412 (15)	0.88454 (17)	0.0733 (10)
O6	0.46548 (16)	1.05938 (11)	0.92006 (13)	0.0427 (7)
N1	0.3198 (2)	0.68024 (15)	1.35199 (18)	0.0506 (10)
N2	0.4858 (2)	0.66536 (15)	0.71325 (17)	0.0456 (9)
N3	0.3578 (2)	1.28030 (15)	0.68068 (18)	0.0477 (9)
C1	0.3158 (2)	0.86114 (17)	1.1454 (2)	0.0372 (10)
C2	0.3135 (2)	0.80178 (16)	1.22069 (19)	0.0373 (10)
C3	0.3322 (3)	0.72121 (17)	1.2052 (2)	0.0470 (11)
C4	0.3354 (3)	0.66315 (19)	1.2734 (2)	0.0549 (13)
C5	0.2994 (2)	0.75971 (18)	1.3694 (2)	0.0426 (10)
C6	0.2815 (3)	0.7777 (2)	1.4548 (2)	0.0567 (12)
C7	0.2608 (3)	0.8547 (2)	1.4768 (2)	0.0644 (14)
C8	0.2557 (3)	0.9187 (2)	1.4147 (2)	0.0566 (12)
C9	0.2729 (3)	0.90404 (18)	1.3318 (2)	0.0466 (11)
C10	0.2956 (2)	0.82397 (17)	1.30585 (19)	0.0371 (9)
C11	0.4845 (2)	0.87364 (15)	0.88500 (18)	0.0336 (9)
C12	0.4823 (2)	0.79992 (15)	0.82552 (19)	0.0338 (9)
C13	0.5075 (2)	0.80853 (17)	0.7444 (2)	0.0420 (10)
C14	0.5075 (3)	0.73995 (18)	0.6898 (2)	0.0471 (11)
C15	0.4610 (2)	0.65485 (16)	0.7944 (2)	0.0390 (10)
C16	0.4388 (3)	0.57510 (18)	0.8204 (2)	0.0537 (13)
C17	0.4165 (3)	0.56137 (19)	0.9005 (3)	0.0602 (13)
C18	0.4145 (3)	0.62605 (18)	0.9599 (2)	0.0553 (11)
C19	0.4325 (2)	0.70432 (17)	0.9368 (2)	0.0443 (11)
C20	0.4567 (2)	0.72081 (16)	0.85339 (19)	0.0356 (9)
C21	0.3686 (3)	1.08793 (16)	0.87468 (19)	0.0373 (10)
C22	0.3669 (2)	1.15372 (16)	0.80556 (19)	0.0343 (9)
C23	0.3456 (3)	1.23251 (17)	0.8256 (2)	0.0470 (11)
C24	0.3423 (3)	1.29366 (18)	0.7608 (2)	0.0528 (11)
C25	0.3782 (2)	1.20227 (18)	0.6586 (2)	0.0402 (10)
C26	0.3917 (3)	1.1866 (2)	0.5712 (2)	0.0581 (14)
C27	0.4122 (3)	1.1097 (2)	0.5471 (2)	0.0669 (14)
C28	0.4202 (3)	1.0448 (2)	0.6076 (2)	0.0633 (12)
C29	0.4065 (3)	1.05687 (18)	0.6915 (2)	0.0490 (11)
C30	0.3841 (2)	1.13619 (16)	0.71960 (19)	0.0371 (9)
O3W	0.0170 (2)	0.96786 (16)	0.11733 (18)	0.0562 (9)
H1WA	0.102 (3)	0.942 (2)	0.911 (3)	0.078 (15)*
H2WA	0.122 (3)	1.057 (2)	0.990 (2)	0.061 (13)*
H3A	0.34270	0.70490	1.14970	0.0560*
H1WB	0.153 (3)	0.874 (2)	0.901 (3)	0.082 (14)*
H4A	0.34970	0.60890	1.26140	0.0660*
H2WB	0.187 (3)	1.092 (2)	1.060 (3)	0.088 (16)*
H6A	0.28410	0.73580	1.49630	0.0680*
H7A	0.24980	0.86570	1.53350	0.0770*
H8A	0.24040	0.97160	1.43040	0.0680*
H9A	0.26970	0.94720	1.29170	0.0560*
H13A	0.52480	0.85990	0.72520	0.0500*
H14A	0.52380	0.74740	0.63420	0.0560*
H16A	0.43960	0.53150	0.78150	0.0640*
H17A	0.40220	0.50840	0.91680	0.0720*
H18A	0.40080	0.61540	1.01580	0.0660*
H19A	0.42880	0.74690	0.97620	0.0530*
H23A	0.33340	1.24550	0.88150	0.0560*
H24A	0.32830	1.34710	0.77580	0.0630*
H26A	0.38650	1.22940	0.53030	0.0700*
H27A	0.42100	1.09990	0.48940	0.0800*
H28A	0.43530	0.99240	0.59000	0.0760*
H29A	0.41170	1.01290	0.73090	0.0590*
H3WA	0.013 (4)	0.923 (2)	0.147 (3)	0.117 (17)*
H3WB	0.072 (3)	0.974 (2)	0.112 (2)	0.055 (13)*

	U11	U22	U33	U12	U13	U23
Y1	0.0339 (1)	0.0235 (1)	0.0277 (1)	−0.0005 (1)	0.0121 (1)	0.0002 (1)
O1	0.1087 (18)	0.0350 (12)	0.0497 (14)	0.0074 (12)	0.0438 (14)	0.0098 (10)
O1W	0.0402 (13)	0.0437 (15)	0.0760 (18)	0.0043 (12)	0.0051 (12)	−0.0294 (14)
O2	0.0862 (16)	0.0393 (12)	0.0402 (13)	−0.0050 (11)	0.0266 (12)	0.0044 (10)
O2W	0.0427 (13)	0.0510 (15)	0.0561 (17)	0.0042 (12)	0.0101 (12)	−0.0255 (13)
O3	0.0395 (11)	0.0357 (11)	0.0551 (13)	−0.0049 (9)	0.0196 (10)	−0.0150 (10)
O4	0.0369 (10)	0.0381 (11)	0.0440 (12)	−0.0005 (9)	0.0186 (9)	−0.0099 (9)
O5	0.0437 (13)	0.0940 (18)	0.0874 (19)	0.0106 (12)	0.0266 (13)	0.0621 (15)
O6	0.0416 (11)	0.0361 (11)	0.0428 (13)	0.0065 (9)	−0.0008 (10)	0.0073 (9)
N1	0.0554 (16)	0.0482 (16)	0.0518 (18)	0.0027 (13)	0.0206 (14)	0.0216 (13)
N2	0.0480 (15)	0.0426 (15)	0.0467 (17)	0.0014 (12)	0.0138 (13)	−0.0152 (12)
N3	0.0466 (15)	0.0436 (16)	0.0516 (18)	0.0016 (12)	0.0113 (13)	0.0206 (13)
C1	0.0385 (16)	0.0398 (17)	0.0346 (18)	−0.0005 (13)	0.0122 (13)	0.0088 (14)
C2	0.0348 (15)	0.0405 (17)	0.0375 (18)	−0.0027 (13)	0.0115 (13)	0.0092 (13)
C3	0.059 (2)	0.0392 (18)	0.048 (2)	0.0031 (15)	0.0235 (16)	0.0075 (15)
C4	0.067 (2)	0.0376 (18)	0.067 (3)	0.0054 (16)	0.0303 (19)	0.0186 (16)
C5	0.0377 (16)	0.0518 (19)	0.0395 (19)	−0.0067 (14)	0.0129 (14)	0.0115 (15)
C6	0.062 (2)	0.071 (2)	0.040 (2)	−0.0121 (18)	0.0190 (17)	0.0155 (17)
C7	0.076 (2)	0.083 (3)	0.041 (2)	−0.013 (2)	0.0276 (19)	−0.0033 (19)
C8	0.063 (2)	0.059 (2)	0.051 (2)	−0.0069 (17)	0.0212 (18)	−0.0075 (17)
C9	0.0524 (18)	0.0486 (19)	0.0389 (19)	−0.0032 (15)	0.0126 (15)	0.0057 (15)
C10	0.0321 (15)	0.0444 (17)	0.0355 (17)	−0.0031 (13)	0.0103 (13)	0.0094 (13)
C11	0.0398 (16)	0.0261 (14)	0.0358 (17)	−0.0004 (12)	0.0122 (13)	−0.0014 (12)
C12	0.0300 (14)	0.0335 (15)	0.0380 (17)	0.0013 (12)	0.0098 (13)	−0.0071 (13)
C13	0.0471 (17)	0.0365 (16)	0.0447 (19)	−0.0017 (13)	0.0166 (15)	−0.0053 (14)
C14	0.0510 (18)	0.054 (2)	0.0373 (18)	0.0011 (15)	0.0139 (15)	−0.0100 (15)
C15	0.0336 (15)	0.0333 (16)	0.048 (2)	0.0001 (12)	0.0077 (14)	−0.0098 (13)
C16	0.055 (2)	0.0370 (18)	0.070 (3)	−0.0015 (15)	0.0186 (18)	−0.0114 (17)
C17	0.061 (2)	0.0358 (18)	0.085 (3)	−0.0042 (16)	0.022 (2)	0.0041 (18)
C18	0.063 (2)	0.0447 (19)	0.065 (2)	0.0022 (16)	0.0291 (19)	0.0097 (17)
C19	0.0488 (18)	0.0429 (18)	0.045 (2)	0.0022 (14)	0.0192 (15)	−0.0037 (14)
C20	0.0294 (14)	0.0349 (16)	0.0412 (18)	0.0008 (12)	0.0075 (13)	−0.0052 (13)
C21	0.0468 (18)	0.0366 (16)	0.0309 (16)	0.0046 (14)	0.0146 (14)	0.0048 (13)
C22	0.0288 (14)	0.0371 (16)	0.0368 (17)	0.0047 (12)	0.0086 (12)	0.0112 (13)
C23	0.0570 (19)	0.0436 (18)	0.0441 (19)	0.0067 (15)	0.0202 (16)	0.0062 (15)
C24	0.060 (2)	0.0336 (17)	0.066 (2)	0.0050 (15)	0.0193 (18)	0.0120 (16)
C25	0.0325 (15)	0.0485 (19)	0.0396 (19)	0.0010 (13)	0.0099 (13)	0.0138 (14)
C26	0.053 (2)	0.083 (3)	0.040 (2)	0.0013 (18)	0.0155 (16)	0.0195 (18)
C27	0.065 (2)	0.097 (3)	0.043 (2)	0.005 (2)	0.0221 (18)	−0.002 (2)
C28	0.069 (2)	0.067 (2)	0.057 (2)	0.0112 (19)	0.0224 (19)	−0.0103 (19)
C29	0.0554 (19)	0.0471 (18)	0.046 (2)	0.0072 (15)	0.0164 (16)	0.0032 (15)
C30	0.0345 (15)	0.0421 (17)	0.0354 (17)	0.0026 (13)	0.0109 (13)	0.0082 (13)
O3W	0.0479 (15)	0.0555 (16)	0.0707 (17)	0.0086 (13)	0.0258 (13)	0.0282 (13)

Y1—Y1i	4.0363 (9)	C11—C12	1.507 (4)
Y1—O1	2.398 (2)	C12—C20	1.420 (4)
Y1—O1W	2.337 (3)	C12—C13	1.360 (4)
Y1—O2	2.461 (2)	C13—C14	1.399 (4)
Y1—O2W	2.370 (3)	C15—C20	1.417 (4)
Y1—O4	2.3245 (19)	C15—C16	1.409 (4)
Y1—O5	2.419 (3)	C16—C17	1.341 (5)
Y1—O6	2.735 (2)	C17—C18	1.400 (5)
Y1—O3i	2.3264 (19)	C18—C19	1.360 (4)
Y1—O6i	2.309 (2)	C19—C20	1.408 (4)
O1—C1	1.248 (3)	C21—C22	1.506 (4)
O2—C1	1.240 (4)	C22—C30	1.414 (4)
O3—C11	1.258 (3)	C22—C23	1.364 (4)
O4—C11	1.241 (3)	C23—C24	1.402 (4)
O5—C21	1.230 (4)	C25—C30	1.418 (4)
O6—C21	1.240 (4)	C25—C26	1.413 (4)
O1W—H1WB	0.78 (4)	C26—C27	1.351 (5)
O1W—H1WA	0.75 (4)	C27—C28	1.395 (4)
O2W—H2WB	0.78 (4)	C28—C29	1.352 (4)
O2W—H2WA	0.78 (3)	C29—C30	1.414 (4)
O3W—H3WB	0.67 (4)	C3—H3A	0.9300
O3W—H3WA	0.87 (4)	C4—H4A	0.9300
N1—C5	1.361 (4)	C6—H6A	0.9300
N1—C4	1.296 (4)	C7—H7A	0.9300
N2—C14	1.316 (4)	C8—H8A	0.9300
N2—C15	1.362 (4)	C9—H9A	0.9300
N3—C24	1.307 (4)	C13—H13A	0.9300
N3—C25	1.358 (4)	C14—H14A	0.9300
C1—C2	1.513 (4)	C16—H16A	0.9300
C2—C3	1.367 (4)	C17—H17A	0.9300
C2—C10	1.423 (4)	C18—H18A	0.9300
C3—C4	1.405 (4)	C19—H19A	0.9300
C5—C10	1.425 (4)	C23—H23A	0.9300
C5—C6	1.411 (4)	C24—H24A	0.9300
C6—C7	1.343 (5)	C26—H26A	0.9300
C7—C8	1.405 (4)	C27—H27A	0.9300
C8—C9	1.360 (4)	C28—H28A	0.9300
C9—C10	1.415 (4)	C29—H29A	0.9300
O1—Y1—O1W	94.29 (9)	C6—C7—C8	120.4 (3)
O1—Y1—O2	52.93 (7)	C7—C8—C9	120.7 (3)
O1—Y1—O2W	71.97 (9)	C8—C9—C10	120.8 (3)
O1—Y1—O4	129.52 (7)	C2—C10—C5	116.9 (2)
O1—Y1—O5	143.80 (8)	C2—C10—C9	125.4 (3)
O1—Y1—O6	147.07 (7)	C5—C10—C9	117.7 (3)
O1—Y1—C1	26.54 (8)	O3—C11—C12	115.0 (2)
O1—Y1—O3i	80.64 (7)	O4—C11—C12	117.3 (2)
O1—Y1—O6i	84.75 (8)	O3—C11—O4	127.7 (2)
O1W—Y1—O2	73.28 (9)	C11—C12—C20	121.2 (2)
O1W—Y1—O2W	70.79 (9)	C11—C12—C13	119.8 (2)
O1W—Y1—O4	76.57 (8)	C13—C12—C20	119.0 (2)
O1W—Y1—O5	77.31 (9)	C12—C13—C14	119.9 (3)
O1W—Y1—O6	117.89 (8)	N2—C14—C13	123.3 (3)
O1W—Y1—C1	83.99 (9)	C16—C15—C20	118.9 (3)
O1W—Y1—O3i	142.91 (8)	N2—C15—C20	122.6 (2)
O1W—Y1—O6i	142.58 (8)	N2—C15—C16	118.4 (3)
O2—Y1—O2W	109.60 (9)	C15—C16—C17	120.7 (3)
O2—Y1—O4	77.23 (7)	C16—C17—C18	120.7 (3)
O2—Y1—O5	147.69 (8)	C17—C18—C19	120.8 (3)
O2—Y1—O6	139.84 (7)	C18—C19—C20	120.0 (3)
O2—Y1—C1	26.42 (8)	C12—C20—C19	123.9 (3)
O2—Y1—O3i	126.54 (7)	C15—C20—C19	118.9 (2)
O2—Y1—O6i	76.61 (8)	C12—C20—C15	117.1 (2)
O2W—Y1—O4	142.44 (9)	O6—C21—C22	119.8 (3)
O2W—Y1—O5	72.03 (9)	O5—C21—C22	118.5 (3)
O2W—Y1—O6	110.45 (8)	O5—C21—O6	121.8 (3)
O2W—Y1—C1	91.51 (9)	C21—C22—C30	122.1 (2)
O2W—Y1—O3i	72.74 (8)	C23—C22—C30	118.8 (3)
O2W—Y1—O6i	141.84 (9)	C21—C22—C23	119.1 (3)
O4—Y1—O5	83.27 (8)	C22—C23—C24	119.1 (3)
O4—Y1—O6	69.39 (7)	N3—C24—C23	124.1 (3)
O4—Y1—C1	103.21 (8)	C26—C25—C30	119.2 (3)
O3i—Y1—O4	133.97 (7)	N3—C25—C26	118.6 (3)
O4—Y1—O6i	75.52 (7)	N3—C25—C30	122.2 (3)
O5—Y1—O6	49.03 (7)	C25—C26—C27	120.1 (3)
O5—Y1—C1	158.26 (8)	C26—C27—C28	120.8 (3)
O3i—Y1—O5	85.37 (8)	C27—C28—C29	121.1 (3)
O5—Y1—O6i	123.02 (8)	C28—C29—C30	120.2 (3)
O6—Y1—C1	152.67 (7)	C25—C30—C29	118.6 (3)
O3i—Y1—O6	69.59 (7)	C22—C30—C29	123.7 (3)
O6—Y1—O6i	74.00 (7)	C22—C30—C25	117.7 (2)
O3i—Y1—C1	103.59 (8)	C2—C3—H3A	120.00
O6i—Y1—C1	78.69 (8)	C4—C3—H3A	120.00
O3i—Y1—O6i	73.97 (7)	C3—C4—H4A	118.00
Y1—O1—C1	94.29 (18)	N1—C4—H4A	118.00
Y1—O2—C1	91.54 (17)	C5—C6—H6A	120.00
Y1i—O3—C11	139.05 (17)	C7—C6—H6A	120.00
Y1—O4—C11	137.44 (17)	C8—C7—H7A	120.00
Y1—O5—C21	102.25 (19)	C6—C7—H7A	120.00
Y1—O6—C21	86.73 (18)	C9—C8—H8A	120.00
Y1—O6—Y1i	106.01 (8)	C7—C8—H8A	120.00
Y1i—O6—C21	167.1 (2)	C8—C9—H9A	120.00
H1WA—O1W—H1WB	115 (4)	C10—C9—H9A	120.00
Y1—O1W—H1WB	122 (3)	C12—C13—H13A	120.00
Y1—O1W—H1WA	119 (3)	C14—C13—H13A	120.00
H2WA—O2W—H2WB	109 (4)	C13—C14—H14A	118.00
Y1—O2W—H2WA	115 (2)	N2—C14—H14A	118.00
Y1—O2W—H2WB	121 (3)	C15—C16—H16A	120.00
H3WA—O3W—H3WB	112 (4)	C17—C16—H16A	120.00
C4—N1—C5	117.7 (3)	C18—C17—H17A	120.00
C14—N2—C15	118.1 (3)	C16—C17—H17A	120.00
C24—N3—C25	118.0 (3)	C17—C18—H18A	120.00
Y1—C1—C2	176.23 (18)	C19—C18—H18A	120.00
Y1—C1—O2	62.04 (15)	C20—C19—H19A	120.00
O1—C1—O2	121.1 (3)	C18—C19—H19A	120.00
O2—C1—C2	118.4 (2)	C22—C23—H23A	120.00
O1—C1—C2	120.5 (3)	C24—C23—H23A	120.00
Y1—C1—O1	59.18 (16)	C23—C24—H24A	118.00
C1—C2—C10	124.9 (2)	N3—C24—H24A	118.00
C3—C2—C10	118.4 (3)	C25—C26—H26A	120.00
C1—C2—C3	116.7 (3)	C27—C26—H26A	120.00
C2—C3—C4	119.7 (3)	C28—C27—H27A	120.00
N1—C4—C3	124.2 (3)	C26—C27—H27A	120.00
N1—C5—C10	123.0 (3)	C27—C28—H28A	120.00
N1—C5—C6	117.3 (3)	C29—C28—H28A	119.00
C6—C5—C10	119.6 (3)	C28—C29—H29A	120.00
C5—C6—C7	120.7 (3)	C30—C29—H29A	120.00
O1W—Y1—O1—C1	67.34 (18)	Y1—O1—C1—C2	175.6 (2)
O2—Y1—O1—C1	2.06 (16)	Y1—O2—C1—O1	3.7 (3)
O2W—Y1—O1—C1	135.54 (19)	Y1—O2—C1—C2	−175.7 (2)
O4—Y1—O1—C1	−8.8 (2)	Y1i—O3—C11—O4	0.8 (5)
O5—Y1—O1—C1	141.65 (17)	Y1i—O3—C11—C12	179.45 (18)
O6—Y1—O1—C1	−124.49 (17)	Y1—O4—C11—O3	−15.6 (4)
O3i—Y1—O1—C1	−149.69 (18)	Y1—O4—C11—C12	165.79 (17)
O6i—Y1—O1—C1	−75.11 (17)	Y1—O5—C21—O6	5.4 (3)
O1—Y1—O2—C1	−2.07 (16)	Y1—O5—C21—C22	−174.5 (2)
O1W—Y1—O2—C1	−111.02 (18)	Y1—O6—C21—O5	−4.6 (3)
O2W—Y1—O2—C1	−49.16 (18)	Y1—O6—C21—C22	175.2 (2)
O4—Y1—O2—C1	169.38 (18)	C5—N1—C4—C3	−0.2 (5)
O5—Y1—O2—C1	−136.32 (17)	C4—N1—C5—C10	−0.6 (4)
O6—Y1—O2—C1	135.30 (16)	C4—N1—C5—C6	179.5 (3)
O3i—Y1—O2—C1	33.5 (2)	C14—N2—C15—C20	0.6 (4)
O6i—Y1—O2—C1	91.48 (17)	C15—N2—C14—C13	0.7 (5)
O6—Y1i—O3—C11	−36.8 (3)	C14—N2—C15—C16	−179.4 (3)
O1i—Y1i—O3—C11	−124.0 (3)	C24—N3—C25—C30	−0.6 (4)
O1Wi—Y1i—O3—C11	151.3 (2)	C25—N3—C24—C23	0.1 (5)
O2i—Y1i—O3—C11	−95.9 (3)	C24—N3—C25—C26	178.2 (3)
O2Wi—Y1i—O3—C11	162.1 (3)	O2—C1—C2—C3	4.2 (4)
O4i—Y1i—O3—C11	13.5 (3)	O1—C1—C2—C10	3.5 (4)
O5i—Y1i—O3—C11	89.5 (3)	O2—C1—C2—C10	−177.0 (3)
O6i—Y1i—O3—C11	41.7 (3)	O1—C1—C2—C3	−175.3 (3)
C1i—Y1i—O3—C11	−110.5 (3)	C10—C2—C3—C4	−1.1 (4)
O1—Y1—O4—C11	−99.1 (3)	C1—C2—C10—C9	2.5 (4)
O1W—Y1—O4—C11	176.5 (3)	C3—C2—C10—C9	−178.7 (3)
O2—Y1—O4—C11	−107.9 (3)	C1—C2—C3—C4	177.8 (3)
O2W—Y1—O4—C11	146.5 (2)	C3—C2—C10—C5	0.4 (4)
O5—Y1—O4—C11	98.0 (2)	C1—C2—C10—C5	−178.4 (2)
O6—Y1—O4—C11	49.4 (2)	C2—C3—C4—N1	1.1 (5)
C1—Y1—O4—C11	−103.1 (2)	N1—C5—C10—C2	0.5 (4)
O3i—Y1—O4—C11	21.1 (3)	C10—C5—C6—C7	0.1 (5)
O6i—Y1—O4—C11	−28.7 (2)	C6—C5—C10—C9	−0.4 (4)
O1—Y1—O5—C21	131.34 (19)	N1—C5—C10—C9	179.6 (3)
O1W—Y1—O5—C21	−148.9 (2)	C6—C5—C10—C2	−179.6 (3)
O2—Y1—O5—C21	−124.1 (2)	N1—C5—C6—C7	−180.0 (3)
O2W—Y1—O5—C21	137.5 (2)	C5—C6—C7—C8	0.5 (5)
O4—Y1—O5—C21	−71.21 (19)	C6—C7—C8—C9	−0.7 (5)
O6—Y1—O5—C21	−2.74 (16)	C7—C8—C9—C10	0.4 (5)
C1—Y1—O5—C21	179.8 (2)	C8—C9—C10—C2	179.3 (3)
O3i—Y1—O5—C21	64.11 (19)	C8—C9—C10—C5	0.2 (5)
O6i—Y1—O5—C21	−3.4 (2)	O3—C11—C12—C20	122.7 (3)
O1—Y1—O6—C21	−126.05 (18)	O3—C11—C12—C13	−56.0 (3)
O1W—Y1—O6—C21	40.58 (18)	O4—C11—C12—C13	122.9 (3)
O2—Y1—O6—C21	137.62 (16)	O4—C11—C12—C20	−58.4 (3)
O2W—Y1—O6—C21	−37.89 (18)	C13—C12—C20—C15	1.0 (4)
O4—Y1—O6—C21	101.90 (16)	C11—C12—C13—C14	178.9 (3)
O5—Y1—O6—C21	2.66 (16)	C20—C12—C13—C14	0.2 (4)
C1—Y1—O6—C21	−179.40 (18)	C11—C12—C20—C15	−177.7 (2)
O3i—Y1—O6—C21	−99.42 (16)	C11—C12—C20—C19	−0.4 (4)
O6i—Y1—O6—C21	−177.89 (17)	C13—C12—C20—C19	178.3 (3)
O1—Y1—O6—Y1i	51.84 (15)	C12—C13—C14—N2	−1.1 (5)
O1W—Y1—O6—Y1i	−141.53 (9)	N2—C15—C20—C12	−1.4 (4)
O2—Y1—O6—Y1i	−44.49 (13)	C16—C15—C20—C12	178.6 (3)
O2W—Y1—O6—Y1i	140.00 (9)	N2—C15—C20—C19	−178.9 (2)
O4—Y1—O6—Y1i	−80.21 (8)	C20—C15—C16—C17	−1.4 (5)
O5—Y1—O6—Y1i	−179.45 (12)	N2—C15—C16—C17	178.6 (3)
C1—Y1—O6—Y1i	−1.51 (19)	C16—C15—C20—C19	1.1 (4)
O3i—Y1—O6—Y1i	78.47 (8)	C15—C16—C17—C18	0.2 (5)
O6i—Y1—O6—Y1i	0.02 (9)	C16—C17—C18—C19	1.5 (6)
O3—Y1i—O6—Y1	72.83 (8)	C17—C18—C19—C20	−1.7 (5)
O1i—Y1i—O6—Y1	154.58 (8)	C18—C19—C20—C12	−176.9 (3)
O1Wi—Y1i—O6—Y1	−115.21 (13)	C18—C19—C20—C15	0.4 (4)
O2i—Y1i—O6—Y1	−152.32 (9)	O5—C21—C22—C23	75.9 (4)
O2Wi—Y1i—O6—Y1	102.90 (13)	O5—C21—C22—C30	−102.7 (3)
O4i—Y1i—O6—Y1	−72.29 (7)	O6—C21—C22—C23	−103.9 (3)
O5i—Y1i—O6—Y1	−0.49 (11)	O6—C21—C22—C30	77.5 (3)
O6i—Y1i—O6—Y1	0.00 (6)	C21—C22—C30—C29	−1.3 (4)
C1i—Y1i—O6—Y1	−179.30 (9)	C23—C22—C30—C25	0.0 (4)
O1W—Y1—C1—O1	−112.28 (18)	C23—C22—C30—C29	−179.9 (3)
O2—Y1—C1—O1	−176.3 (3)	C21—C22—C30—C25	178.6 (3)
O2W—Y1—C1—O1	−41.78 (18)	C21—C22—C23—C24	−179.1 (3)
O4—Y1—C1—O1	173.06 (17)	C30—C22—C23—C24	−0.5 (4)
O5—Y1—C1—O1	−81.7 (3)	C22—C23—C24—N3	0.4 (5)
O6—Y1—C1—O1	102.5 (2)	N3—C25—C26—C27	179.9 (3)
O3i—Y1—C1—O1	30.82 (18)	C30—C25—C26—C27	−1.2 (5)
O6i—Y1—C1—O1	101.06 (18)	N3—C25—C30—C22	0.5 (4)
O1—Y1—C1—O2	176.3 (3)	N3—C25—C30—C29	−179.6 (3)
O1W—Y1—C1—O2	64.02 (17)	C26—C25—C30—C22	−178.3 (3)
O2W—Y1—C1—O2	134.52 (17)	C26—C25—C30—C29	1.6 (4)
O4—Y1—C1—O2	−10.64 (18)	C25—C26—C27—C28	0.1 (5)
O5—Y1—C1—O2	94.7 (3)	C26—C27—C28—C29	0.7 (5)
O6—Y1—C1—O2	−81.2 (2)	C27—C28—C29—C30	−0.2 (5)
O3i—Y1—C1—O2	−152.88 (16)	C28—C29—C30—C22	179.0 (3)
O6i—Y1—C1—O2	−82.64 (17)	C28—C29—C30—C25	−0.9 (5)
Y1—O1—C1—O2	−3.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O3Wii	0.75 (4)	1.99 (4)	2.727 (4)	168 (3)
O2W—H2WA···O3Wii	0.78 (3)	2.00 (3)	2.751 (4)	161 (3)
O3W—H3WA···N2iii	0.87 (4)	1.84 (4)	2.708 (4)	172 (4)
O1W—H1WB···N3iv	0.78 (4)	1.96 (4)	2.735 (4)	173 (4)
O2W—H2WB···N1v	0.78 (4)	1.99 (4)	2.739 (4)	161 (4)
O3W—H3WB···O2Wvi	0.67 (4)	2.30 (3)	2.865 (4)	143 (3)
C3—H3A···O2	0.93	2.39	2.721 (4)	101
C9—H9A···O1	0.93	2.24	2.868 (4)	125
C19—H19A···O2	0.93	2.56	3.421 (4)	154
C19—H19A···O4	0.93	2.55	3.081 (3)	117

Table 1

Selected geometric parameters (Å, °)

Y1—O1	2.398 (2)
Y1—O1W	2.337 (3)
Y1—O2	2.461 (2)
Y1—O2W	2.370 (3)
Y1—O4	2.3245 (19)
Y1—O5	2.419 (3)
Y1—O6	2.735 (2)
Y1—O3i	2.3264 (19)
Y1—O6i	2.309 (2)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O3Wii	0.75 (4)	1.99 (4)	2.727 (4)	168 (3)
O2W—H2WA⋯O3Wii	0.78 (3)	2.00 (3)	2.751 (4)	161 (3)
O3W—H3WA⋯N2iii	0.87 (4)	1.84 (4)	2.708 (4)	172 (4)
O1W—H1WB⋯N3iv	0.78 (4)	1.96 (4)	2.735 (4)	173 (4)
O2W—H2WB⋯N1v	0.78 (4)	1.99 (4)	2.739 (4)	161 (4)
O3W—H3WB⋯O2Wvi	0.67 (4)	2.30 (3)	2.865 (4)	143 (3)

Symmetry codes: (ii) ; (iii) ; (iv) ; (v) ; (vi) .