Tetra­aqua­hexa­kis(μ₂-quinoline-4-carboxyl­ato)diyttrium(III) dihydrate

In the title centrosymmetric binuclear complex, [Y₂(C₁₀H₆NO₂)₆(H₂O)₄]·2H₂O, each Y^III atom is nine-coordin­ated by nine O atoms from five ligands and two water mol­ecules in a slightly distorted monocapped square-anti­prismatic 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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.034
• wR factor = 0.073
• Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found





Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Y1     --  O6      ..      23.13 su
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         O5

Alert level C
            Value of measurement temperature given =   293.000
            Value of melting point given =     0.000
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O6     --  C21     ..       5.77 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Y1     --  O2      ..       7.47 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         Y1
PLAT354_ALERT_3_C Short   O-H Bond (0.82A)   O3W    -   H3WB   ...       0.67 Ang.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.95

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.946
            Tmax scaled      0.573 Tmin scaled      0.535
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          6

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

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

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S1. Comment

Some crystal structures of transition metal complexes with the ligand 4-quinolinecarboxylic acid (HL) have been published previously, for example, with cadmium(II) (Morsy & Vratislav, 2006; Chen et al., 2002), copper(II), cobalt(II) and manganese(II) (Bu et al., 2005). However, no rare earth metal complexes of HL have been reported to date. Herein, we report on the synthesis and crystal structure of a new binuclear yittrium(III) complex of 4-quinolinecarboxylic acid, (I).

The molecuar structute of title compound (I), a centrosymmetric binuclear complex, is illustrated in Fig. 1. The complex is compossed of two yttrium(III) atoms and six 4-quinolinecarboxylate ligands, along with four coordinated and two uncoordinated water molecules. Each yttrium atom is nine-coordinated, with nine oxygen atoms from five ligands and two water molecules, showing a slightly distorted monocapped square-antiprism coordination environment (Table 1). The Y1—O bond distances vary from 2.309 (2) to 2.735 (2) Å, while the Y1···Y1ⁱ separation is 4.0363 (9) Å [Symmetry code: (i) -x + 1, -y + 2, -z + 2]. The six 4-quinolinecarboxylate ligands adopt three different coordination modes; chelating, bridging, and a mixed mode of chelating and bridging (Table 1).

In the crystal structure O—H···O and O—H···N hydrogen bonds link the binuclear complexes and uncoordinated water molecules to form a three-dimensional network (Table 2).

Related literature

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

S2. Experimental

A mixture of 4-quinolinecarboxylic acid, sodium hydroxide and yttrium nitrate, in the molar ratio 3:6:1, were dissolved in a mixture of ethanol and water. The resulting solution was filtered and the filtrate allowed to stand in the air for several days. Finally colorless block-like crystals, suitable for X-ray analysis, were obtained with a yield of 25%.

S3. Refinement

The water H atoms were located in difference Fourier maps and freely refined; O—H = 0.67 (3) - 0.88 (4) Å, with U_iso(H) = 1.5U_eq(O). The C-bound H atoms were included in calculated positions and treated as riding atoms, with C—H = 0.93 Å and U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 (Sheldrick, 2008).

Figures

Fig. 1. The molecular structure of complex (I), with displacement ellipsoids drawn at the 30% probability level (C-bound H-atoms have been removed for clarity; Symmetry code: (A) -x + 1, -y + 2, -z + 2])

Tetraaquahexakis(µ₂-quinoline-4-carboxylato)diyttrium(III) dihydrate

Crystal data

[Y2(C10H6NO2)6(H2O)4]·2H2O	F(000) = 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 = 3.0–27.5°
b = 16.361 (3) Å	µ = 2.15 mm^−1
c = 15.312 (3) Å	T = 293 K
β = 106.03 (3)°	Block, colorless
V = 2798.7 (10) Å^3	0.30 × 0.28 × 0.26 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	4898 independent reflections
Radiation source: fine-focus sealed tube	3615 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ϕ and ω scans	θmax = 25.0°, θmin = 3.0°
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

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.073	H atoms treated by a mixture of independent and constrained refinement
S = 0.91	w = 1/[σ^2(Fo^2) + (0.0401P)^2] where P = (Fo^2 + 2Fc^2)/3
4898 reflections	(Δ/σ)max = 0.003
412 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

Special details

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.

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

	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)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

Y1—Y1^i	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—O3^i	2.3264 (19)	C18—C19	1.360 (4)
Y1—O6^i	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—O3^i	80.64 (7)	O4—C11—C12	117.3 (2)
O1—Y1—O6^i	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—O3^i	142.91 (8)	N2—C15—C20	122.6 (2)
O1W—Y1—O6^i	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—O3^i	126.54 (7)	C15—C20—C19	118.9 (2)
O2—Y1—O6^i	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—O3^i	72.74 (8)	C23—C22—C30	118.8 (3)
O2W—Y1—O6^i	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)
O3^i—Y1—O4	133.97 (7)	N3—C25—C26	118.6 (3)
O4—Y1—O6^i	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)
O3^i—Y1—O5	85.37 (8)	C27—C28—C29	121.1 (3)
O5—Y1—O6^i	123.02 (8)	C28—C29—C30	120.2 (3)
O6—Y1—C1	152.67 (7)	C25—C30—C29	118.6 (3)
O3^i—Y1—O6	69.59 (7)	C22—C30—C29	123.7 (3)
O6—Y1—O6^i	74.00 (7)	C22—C30—C25	117.7 (2)
O3^i—Y1—C1	103.59 (8)	C2—C3—H3A	120.00
O6^i—Y1—C1	78.69 (8)	C4—C3—H3A	120.00
O3^i—Y1—O6^i	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
Y1^i—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—Y1^i	106.01 (8)	C7—C8—H8A	120.00
Y1^i—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)	Y1^i—O3—C11—O4	0.8 (5)
O5—Y1—O1—C1	141.65 (17)	Y1^i—O3—C11—C12	179.45 (18)
O6—Y1—O1—C1	−124.49 (17)	Y1—O4—C11—O3	−15.6 (4)
O3^i—Y1—O1—C1	−149.69 (18)	Y1—O4—C11—C12	165.79 (17)
O6^i—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)
O3^i—Y1—O2—C1	33.5 (2)	C14—N2—C15—C20	0.6 (4)
O6^i—Y1—O2—C1	91.48 (17)	C15—N2—C14—C13	0.7 (5)
O6—Y1^i—O3—C11	−36.8 (3)	C14—N2—C15—C16	−179.4 (3)
O1^i—Y1^i—O3—C11	−124.0 (3)	C24—N3—C25—C30	−0.6 (4)
O1W^i—Y1^i—O3—C11	151.3 (2)	C25—N3—C24—C23	0.1 (5)
O2^i—Y1^i—O3—C11	−95.9 (3)	C24—N3—C25—C26	178.2 (3)
O2W^i—Y1^i—O3—C11	162.1 (3)	O2—C1—C2—C3	4.2 (4)
O4^i—Y1^i—O3—C11	13.5 (3)	O1—C1—C2—C10	3.5 (4)
O5^i—Y1^i—O3—C11	89.5 (3)	O2—C1—C2—C10	−177.0 (3)
O6^i—Y1^i—O3—C11	41.7 (3)	O1—C1—C2—C3	−175.3 (3)
C1^i—Y1^i—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)
O3^i—Y1—O4—C11	21.1 (3)	C10—C5—C6—C7	0.1 (5)
O6^i—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)
O3^i—Y1—O5—C21	64.11 (19)	C8—C9—C10—C5	0.2 (5)
O6^i—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)
O3^i—Y1—O6—C21	−99.42 (16)	C11—C12—C20—C19	−0.4 (4)
O6^i—Y1—O6—C21	−177.89 (17)	C13—C12—C20—C19	178.3 (3)
O1—Y1—O6—Y1^i	51.84 (15)	C12—C13—C14—N2	−1.1 (5)
O1W—Y1—O6—Y1^i	−141.53 (9)	N2—C15—C20—C12	−1.4 (4)
O2—Y1—O6—Y1^i	−44.49 (13)	C16—C15—C20—C12	178.6 (3)
O2W—Y1—O6—Y1^i	140.00 (9)	N2—C15—C20—C19	−178.9 (2)
O4—Y1—O6—Y1^i	−80.21 (8)	C20—C15—C16—C17	−1.4 (5)
O5—Y1—O6—Y1^i	−179.45 (12)	N2—C15—C16—C17	178.6 (3)
C1—Y1—O6—Y1^i	−1.51 (19)	C16—C15—C20—C19	1.1 (4)
O3^i—Y1—O6—Y1^i	78.47 (8)	C15—C16—C17—C18	0.2 (5)
O6^i—Y1—O6—Y1^i	0.02 (9)	C16—C17—C18—C19	1.5 (6)
O3—Y1^i—O6—Y1	72.83 (8)	C17—C18—C19—C20	−1.7 (5)
O1^i—Y1^i—O6—Y1	154.58 (8)	C18—C19—C20—C12	−176.9 (3)
O1W^i—Y1^i—O6—Y1	−115.21 (13)	C18—C19—C20—C15	0.4 (4)
O2^i—Y1^i—O6—Y1	−152.32 (9)	O5—C21—C22—C23	75.9 (4)
O2W^i—Y1^i—O6—Y1	102.90 (13)	O5—C21—C22—C30	−102.7 (3)
O4^i—Y1^i—O6—Y1	−72.29 (7)	O6—C21—C22—C23	−103.9 (3)
O5^i—Y1^i—O6—Y1	−0.49 (11)	O6—C21—C22—C30	77.5 (3)
O6^i—Y1^i—O6—Y1	0.00 (6)	C21—C22—C30—C29	−1.3 (4)
C1^i—Y1^i—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)
O3^i—Y1—C1—O1	30.82 (18)	C30—C25—C26—C27	−1.2 (5)
O6^i—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)
O3^i—Y1—C1—O2	−152.88 (16)	C28—C29—C30—C22	179.0 (3)
O6^i—Y1—C1—O2	−82.64 (17)	C28—C29—C30—C25	−0.9 (5)
Y1—O1—C1—O2	−3.8 (3)

Symmetry code: (i) −x+1, −y+2, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O3W^ii	0.75 (4)	1.99 (4)	2.727 (4)	168 (3)
O2W—H2WA···O3W^ii	0.78 (3)	2.00 (3)	2.751 (4)	161 (3)
O3W—H3WA···N2^iii	0.87 (4)	1.84 (4)	2.708 (4)	172 (4)
O1W—H1WB···N3^iv	0.78 (4)	1.96 (4)	2.735 (4)	173 (4)
O2W—H2WB···N1^v	0.78 (4)	1.99 (4)	2.739 (4)	161 (4)
O3W—H3WB···O2W^vi	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

Symmetry codes: (ii) −x, −y+2, −z+1; (iii) x−1/2, −y+3/2, z−1/2; (iv) −x+1/2, y−1/2, −z+3/2; (v) −x+1/2, y+1/2, −z+5/2; (vi) x, y, z−1.