Bis(2,6-dihy-droxy-benzoato-κO,O)(nitrato-κO,O')bis-(1,10-phenanthroline-κN,N')gadolinium(III).

In the mononuclear title complex, [Gd(C(7)H(5)O(3))(2)(NO(3))(C(12)H(8)N(2))(2)], the Gd atom is in a pseudo-bicapped square-anti-prismatic geometry formed by four N atoms from two chelating 1,10-phenanthroline (phen) ligands and by six O atoms, four from two 2,6-dihy-droxy-benzoate (DHB) ligands and the other two from a nitrate anion. π-π stacking inter-actions between phen-DHB [centroid-centroid distances = 3.5334 (18) and 3.8414 (16) Å] and phen-phen [face-to-face separation = 3.4307 (17) Å] ligands of adjacent complex molecules stabilize the crystal structure. Intra-molecular O-H⋯O hydrogen bonds are observed in the DHB ligands.

Related literature

For background to the complexation of Gd(III) ions with multidentate ligands with O- and N-donors, see: Kido & Okamoto (2002 ▶); Lauffer (1990 ▶). For related structures, see: Ma et al. (2010 ▶); Wang et al. (2008 ▶); Xia et al. (2007 ▶).

Experimental

Crystal data

[Gd(C7H5O3)2(NO3)(C12H8N2)2]

M = 885.89

Monoclinic,

a = 11.1623 (2) Å

b = 26.7666 (4) Å

c = 14.2979 (4) Å

β = 127.445 (1)°

V = 3391.60 (12) Å3

Z = 4

Mo Kα radiation

μ = 2.03 mm−1

T = 298 K

0.46 × 0.42 × 0.40 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer

Absorption correction: multi-scan [ABSPACK in CrysAlis PRO RED (Oxford Diffraction, 2006 ▶)] T min = 0.455, T max = 0.497

18394 measured reflections

5979 independent reflections

4815 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.043

S = 1.01

5979 reflections

496 parameters

12 restraints

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.47 e Å−3

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2006 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Berndt, 1999 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810047124/pk2280sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047124/pk2280Isup2.hkl

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

[Gd(C7H5O3)2(NO3)(C12H8N2)2]	F(000) = 1764
Mr = 885.89	Dx = 1.735 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11955 reflections
a = 11.1623 (2) Å	θ = 2.9–29.1°
b = 26.7666 (4) Å	µ = 2.03 mm−1
c = 14.2979 (4) Å	T = 298 K
β = 127.445 (1)°	Block, orange
V = 3391.60 (12) Å3	0.46 × 0.42 × 0.40 mm
Z = 4

Oxford Diffraction Gemini S Ultra diffractometer	5979 independent reflections
Radiation source: Enhance (Mo) X-ray Source	4815 reflections with I > 2σ(I)
graphite	Rint = 0.024
Detector resolution: 15.9 pixels mm-1	θmax = 25.0°, θmin = 2.9°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)	k = −31→31
Tmin = 0.455, Tmax = 0.497	l = −17→15
18394 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.043	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.020P)2] where P = (Fo2 + 2Fc2)/3
5979 reflections	(Δ/σ)max = 0.001
496 parameters	Δρmax = 0.46 e Å−3
12 restraints	Δρmin = −0.47 e Å−3

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
Gd1	0.930008 (14)	0.862284 (4)	0.221059 (11)	0.03241 (5)
O1	0.8890 (2)	0.91866 (6)	0.05856 (15)	0.0451 (5)
O2	0.8450 (2)	0.83835 (7)	0.02180 (15)	0.0443 (4)
O3	0.7536 (2)	0.80218 (7)	−0.17849 (17)	0.0606 (5)
H3	0.7812	0.8019	−0.1106	0.091*
O4	0.8349 (3)	0.97874 (7)	−0.1046 (2)	0.0816 (7)
H4	0.8533	0.9705	−0.0419	0.122*
O5	0.69658 (19)	0.81249 (6)	0.13465 (16)	0.0434 (4)
O6	0.66669 (19)	0.89321 (6)	0.09915 (17)	0.0505 (5)
O7	0.4812 (2)	0.75919 (7)	0.10366 (17)	0.0542 (5)
H7	0.5652	0.7649	0.1220	0.081*
O8	0.4200 (2)	0.93646 (8)	0.0290 (2)	0.0753 (7)
H8	0.5060	0.9337	0.0492	0.113*
O9	0.8459 (2)	0.87228 (7)	0.34724 (17)	0.0506 (5)
O10	0.9519 (2)	0.80131 (6)	0.37257 (17)	0.0492 (5)
O11	0.8610 (3)	0.81841 (9)	0.46695 (19)	0.0817 (7)
N1	0.9754 (2)	0.95435 (7)	0.29187 (19)	0.0368 (5)
N2	1.1640 (2)	0.88032 (7)	0.43955 (18)	0.0357 (5)
N3	1.1797 (2)	0.86803 (7)	0.24844 (18)	0.0375 (5)
N4	1.0554 (2)	0.77981 (7)	0.23851 (18)	0.0355 (5)
N5	0.8865 (3)	0.82976 (9)	0.3979 (2)	0.0470 (6)
C1	0.8820 (3)	0.99069 (10)	0.2201 (3)	0.0471 (7)
H1	0.8063	0.9831	0.1414	0.057*
C2	0.8935 (4)	1.03981 (10)	0.2589 (3)	0.0534 (8)
H2	0.8261	1.0641	0.2065	0.064*
C3	1.0030 (4)	1.05157 (10)	0.3726 (3)	0.0517 (8)
H3A	1.0116	1.0841	0.3989	0.062*
C4	1.1037 (3)	1.01476 (9)	0.4510 (3)	0.0407 (7)
C5	1.0847 (3)	0.96619 (9)	0.4060 (2)	0.0343 (6)
C6	1.2220 (3)	1.02442 (10)	0.5721 (3)	0.0510 (8)
H6	1.2346	1.0566	0.6013	0.061*
C7	1.3153 (3)	0.98818 (11)	0.6447 (3)	0.0530 (8)
H7A	1.3911	0.9957	0.7234	0.064*
C8	1.3011 (3)	0.93797 (10)	0.6037 (2)	0.0403 (6)
C9	1.1850 (3)	0.92708 (9)	0.4844 (2)	0.0347 (6)
C10	1.3956 (3)	0.89923 (11)	0.6760 (3)	0.0496 (7)
H10	1.4723	0.9051	0.7554	0.060*
C11	1.3754 (3)	0.85270 (10)	0.6303 (3)	0.0475 (7)
H11	1.4387	0.8265	0.6774	0.057*
C12	1.2586 (3)	0.84516 (10)	0.5121 (2)	0.0421 (7)
H12	1.2458	0.8132	0.4818	0.050*
C13	1.2402 (3)	0.91126 (10)	0.2505 (2)	0.0475 (7)
H13	1.1814	0.9400	0.2262	0.057*
C14	1.3874 (3)	0.91551 (12)	0.2872 (3)	0.0566 (8)
H14	1.4255	0.9465	0.2875	0.068*
C15	1.4749 (3)	0.87395 (12)	0.3226 (3)	0.0565 (8)
H15	1.5739	0.8765	0.3485	0.068*
C16	1.4167 (3)	0.82720 (11)	0.3202 (2)	0.0436 (7)
C17	1.2668 (3)	0.82630 (9)	0.2817 (2)	0.0360 (6)
C18	1.1987 (3)	0.77906 (9)	0.2718 (2)	0.0350 (6)
C19	1.2788 (3)	0.73454 (10)	0.2958 (2)	0.0412 (7)
C20	1.4327 (3)	0.73749 (12)	0.3397 (2)	0.0541 (8)
H20	1.4884	0.7082	0.3602	0.065*
C21	1.4990 (3)	0.78140 (12)	0.3522 (2)	0.0542 (8)
H21	1.5998	0.7821	0.3820	0.065*
C22	1.2026 (3)	0.68959 (10)	0.2755 (2)	0.0482 (7)
H22	1.2507	0.6593	0.2871	0.058*
C23	1.0593 (3)	0.69013 (10)	0.2392 (2)	0.0478 (7)
H23	1.0075	0.6604	0.2246	0.057*
C24	0.9899 (3)	0.73592 (10)	0.2237 (2)	0.0435 (7)
H24	0.8926	0.7358	0.2020	0.052*
C25	0.8459 (3)	0.88219 (10)	−0.0120 (2)	0.0375 (6)
C26	0.7966 (3)	0.89003 (9)	−0.1327 (2)	0.0357 (6)
C27	0.7529 (3)	0.84952 (10)	−0.2109 (2)	0.0420 (7)
C28	0.7051 (3)	0.85738 (11)	−0.3242 (3)	0.0534 (8)
H28	0.6756	0.8305	−0.3752	0.064*
C29	0.7015 (3)	0.90493 (13)	−0.3609 (3)	0.0605 (8)
H29	0.6690	0.9100	−0.4375	0.073*
C30	0.7443 (4)	0.94522 (12)	−0.2884 (3)	0.0633 (9)
H30	0.7408	0.9772	−0.3154	0.076*
C31	0.7930 (3)	0.93800 (11)	−0.1744 (3)	0.0512 (7)
C32	0.6141 (3)	0.85113 (10)	0.1004 (2)	0.0422 (7)
C33	0.4596 (3)	0.84803 (9)	0.0660 (2)	0.0386 (6)
C34	0.3692 (3)	0.89083 (11)	0.0327 (2)	0.0508 (7)
C35	0.2258 (3)	0.88797 (13)	0.0027 (3)	0.0600 (8)
H35	0.1660	0.9164	−0.0201	0.072*
C36	0.1739 (3)	0.84251 (13)	0.0071 (3)	0.0583 (8)
H36	0.0775	0.8406	−0.0132	0.070*
C37	0.2579 (3)	0.79927 (12)	0.0404 (2)	0.0520 (8)
H37	0.2190	0.7690	0.0427	0.062*
C38	0.4019 (3)	0.80189 (11)	0.0705 (2)	0.0426 (7)

	U11	U22	U33	U12	U13	U23
Gd1	0.03358 (7)	0.02755 (7)	0.03929 (8)	0.00033 (6)	0.02381 (6)	−0.00046 (6)
O1	0.0562 (12)	0.0395 (11)	0.0428 (12)	−0.0024 (9)	0.0317 (10)	−0.0020 (9)
O2	0.0514 (12)	0.0361 (11)	0.0439 (12)	−0.0019 (9)	0.0282 (10)	0.0033 (9)
O3	0.0691 (14)	0.0414 (12)	0.0488 (13)	−0.0016 (10)	0.0242 (11)	−0.0072 (10)
O4	0.141 (2)	0.0415 (13)	0.0582 (15)	−0.0182 (14)	0.0586 (16)	−0.0043 (11)
O5	0.0347 (10)	0.0386 (11)	0.0571 (13)	0.0035 (9)	0.0281 (10)	0.0013 (9)
O6	0.0426 (11)	0.0421 (12)	0.0640 (14)	0.0030 (9)	0.0310 (11)	0.0097 (9)
O7	0.0449 (11)	0.0497 (12)	0.0694 (15)	0.0009 (10)	0.0354 (12)	0.0074 (10)
O8	0.0592 (14)	0.0560 (14)	0.102 (2)	0.0174 (12)	0.0444 (14)	0.0139 (13)
O9	0.0563 (11)	0.0455 (12)	0.0608 (13)	0.0035 (9)	0.0412 (10)	−0.0022 (9)
O10	0.0541 (12)	0.0383 (11)	0.0579 (13)	0.0010 (9)	0.0354 (11)	0.0016 (9)
O11	0.0799 (16)	0.124 (2)	0.0590 (16)	−0.0099 (15)	0.0517 (14)	0.0115 (14)
N1	0.0465 (13)	0.0265 (11)	0.0444 (15)	0.0023 (10)	0.0312 (12)	0.0038 (10)
N2	0.0358 (12)	0.0318 (12)	0.0413 (13)	0.0038 (10)	0.0244 (11)	0.0025 (10)
N3	0.0377 (12)	0.0396 (13)	0.0400 (13)	−0.0057 (10)	0.0261 (11)	−0.0030 (10)
N4	0.0362 (12)	0.0331 (12)	0.0399 (14)	−0.0023 (10)	0.0244 (11)	−0.0025 (10)
N5	0.0413 (12)	0.0588 (15)	0.0441 (14)	−0.0096 (11)	0.0275 (11)	−0.0031 (11)
C1	0.0557 (18)	0.0389 (16)	0.054 (2)	0.0056 (14)	0.0374 (17)	0.0061 (14)
C2	0.074 (2)	0.0281 (16)	0.077 (3)	0.0104 (15)	0.056 (2)	0.0109 (15)
C3	0.075 (2)	0.0262 (15)	0.083 (3)	−0.0060 (15)	0.063 (2)	−0.0072 (16)
C4	0.0507 (17)	0.0308 (15)	0.062 (2)	−0.0094 (13)	0.0457 (17)	−0.0074 (14)
C5	0.0390 (15)	0.0303 (14)	0.0474 (18)	−0.0039 (12)	0.0334 (15)	−0.0031 (12)
C6	0.061 (2)	0.0370 (17)	0.076 (2)	−0.0197 (15)	0.052 (2)	−0.0204 (16)
C7	0.0485 (18)	0.057 (2)	0.059 (2)	−0.0200 (16)	0.0356 (17)	−0.0208 (17)
C8	0.0352 (15)	0.0462 (17)	0.0482 (18)	−0.0081 (13)	0.0299 (15)	−0.0077 (14)
C9	0.0380 (15)	0.0339 (15)	0.0472 (18)	−0.0058 (12)	0.0336 (15)	−0.0044 (12)
C10	0.0332 (15)	0.068 (2)	0.0407 (18)	−0.0031 (14)	0.0189 (14)	−0.0040 (15)
C11	0.0393 (16)	0.055 (2)	0.0460 (19)	0.0062 (14)	0.0246 (15)	0.0073 (14)
C12	0.0449 (16)	0.0393 (16)	0.0453 (19)	0.0035 (13)	0.0291 (16)	0.0007 (13)
C13	0.0537 (18)	0.0454 (17)	0.0510 (19)	−0.0092 (14)	0.0358 (16)	−0.0039 (14)
C14	0.0531 (19)	0.060 (2)	0.061 (2)	−0.0240 (17)	0.0367 (18)	−0.0091 (17)
C15	0.0399 (17)	0.083 (2)	0.050 (2)	−0.0146 (17)	0.0292 (16)	−0.0107 (17)
C16	0.0357 (15)	0.0623 (19)	0.0350 (17)	−0.0046 (14)	0.0226 (14)	−0.0050 (14)
C17	0.0355 (14)	0.0444 (16)	0.0291 (15)	−0.0008 (13)	0.0203 (13)	−0.0025 (12)
C18	0.0373 (15)	0.0391 (15)	0.0315 (15)	0.0014 (12)	0.0224 (13)	−0.0012 (12)
C19	0.0457 (17)	0.0467 (17)	0.0358 (17)	0.0133 (14)	0.0271 (15)	0.0033 (13)
C20	0.0507 (19)	0.064 (2)	0.048 (2)	0.0203 (16)	0.0303 (17)	0.0051 (16)
C21	0.0359 (16)	0.079 (2)	0.0451 (19)	0.0125 (16)	0.0234 (15)	0.0017 (16)
C22	0.065 (2)	0.0359 (16)	0.0473 (19)	0.0130 (15)	0.0358 (17)	0.0019 (13)
C23	0.0609 (19)	0.0329 (16)	0.0479 (19)	0.0004 (14)	0.0321 (17)	−0.0024 (13)
C24	0.0462 (16)	0.0359 (16)	0.0477 (19)	−0.0007 (13)	0.0282 (15)	−0.0019 (13)
C25	0.0289 (14)	0.0428 (16)	0.0396 (17)	−0.0007 (12)	0.0201 (13)	−0.0018 (14)
C26	0.0284 (13)	0.0377 (15)	0.0392 (16)	0.0025 (12)	0.0196 (13)	0.0011 (12)
C27	0.0313 (14)	0.0457 (18)	0.0432 (18)	0.0026 (12)	0.0195 (14)	−0.0016 (13)
C28	0.0468 (17)	0.063 (2)	0.0461 (19)	−0.0013 (16)	0.0263 (16)	−0.0140 (16)
C29	0.065 (2)	0.076 (2)	0.045 (2)	−0.0119 (18)	0.0356 (18)	−0.0035 (18)
C30	0.085 (2)	0.057 (2)	0.050 (2)	−0.0113 (18)	0.042 (2)	0.0047 (17)
C31	0.062 (2)	0.0495 (19)	0.0443 (19)	−0.0095 (15)	0.0333 (17)	−0.0050 (15)
C32	0.0373 (15)	0.0504 (19)	0.0384 (17)	0.0010 (14)	0.0227 (14)	−0.0002 (13)
C33	0.0311 (14)	0.0488 (17)	0.0330 (16)	0.0065 (12)	0.0180 (13)	0.0033 (12)
C34	0.0482 (18)	0.054 (2)	0.0454 (19)	0.0092 (15)	0.0258 (16)	0.0042 (15)
C35	0.0411 (18)	0.080 (2)	0.054 (2)	0.0259 (17)	0.0260 (16)	0.0097 (17)
C36	0.0330 (16)	0.097 (3)	0.0443 (19)	0.0055 (17)	0.0231 (16)	0.0017 (17)
C37	0.0391 (17)	0.075 (2)	0.0426 (19)	−0.0039 (16)	0.0251 (15)	0.0011 (15)
C38	0.0367 (15)	0.0589 (19)	0.0315 (16)	0.0004 (14)	0.0203 (14)	0.0005 (13)

Gd1—O6	2.4764 (17)	C8—C10	1.389 (4)
Gd1—O2	2.4781 (17)	C8—C9	1.409 (4)
Gd1—O5	2.4854 (16)	C10—C11	1.360 (4)
Gd1—O9	2.5039 (17)	C10—H10	0.9300
Gd1—N4	2.5433 (19)	C11—C12	1.384 (4)
Gd1—O1	2.5673 (16)	C11—H11	0.9300
Gd1—N3	2.5728 (19)	C12—H12	0.9300
Gd1—N1	2.5943 (19)	C13—C14	1.392 (4)
Gd1—O10	2.6022 (17)	C13—H13	0.9300
Gd1—N2	2.625 (2)	C14—C15	1.359 (4)
Gd1—C32	2.847 (3)	C14—H14	0.9300
Gd1—C25	2.910 (3)	C15—C16	1.401 (4)
O1—C25	1.270 (3)	C15—H15	0.9300
O2—C25	1.271 (3)	C16—C17	1.407 (3)
O3—C27	1.347 (3)	C16—C21	1.430 (4)
O3—H3	0.8201	C17—C18	1.438 (3)
O4—C31	1.355 (3)	C18—C19	1.402 (3)
O4—H4	0.8201	C19—C22	1.399 (4)
O5—C32	1.268 (3)	C19—C20	1.428 (4)
O6—C32	1.275 (3)	C20—C21	1.342 (4)
O7—C38	1.343 (3)	C20—H20	0.9300
O7—H7	0.8199	C21—H21	0.9300
O8—C34	1.361 (3)	C22—C23	1.348 (4)
O8—H8	0.8201	C22—H22	0.9300
O9—N5	1.275 (3)	C23—C24	1.394 (4)
O10—N5	1.252 (3)	C23—H23	0.9300
O11—N5	1.220 (3)	C24—H24	0.9300
N1—C1	1.336 (3)	C25—C26	1.473 (3)
N1—C5	1.353 (3)	C26—C31	1.406 (3)
N2—C12	1.321 (3)	C26—C27	1.414 (3)
N2—C9	1.360 (3)	C27—C28	1.380 (4)
N3—C13	1.331 (3)	C28—C29	1.368 (4)
N3—C17	1.363 (3)	C28—H28	0.9300
N4—C24	1.331 (3)	C29—C30	1.365 (4)
N4—C18	1.364 (3)	C29—H29	0.9300
C1—C2	1.402 (3)	C30—C31	1.384 (4)
C1—H1	0.9300	C30—H30	0.9300
C2—C3	1.349 (4)	C32—C33	1.480 (3)
C2—H2	0.9300	C33—C34	1.405 (4)
C3—C4	1.400 (4)	C33—C38	1.413 (3)
C3—H3A	0.9300	C34—C35	1.385 (4)
C4—C5	1.408 (3)	C35—C36	1.366 (4)
C4—C6	1.424 (4)	C35—H35	0.9300
C5—C9	1.442 (3)	C36—C37	1.379 (4)
C6—C7	1.338 (4)	C36—H36	0.9300
C6—H6	0.9300	C37—C38	1.390 (3)
C7—C8	1.436 (4)	C37—H37	0.9300
C7—H7A	0.9300
O6—Gd1—O2	79.42 (6)	N1—C5—C9	118.2 (2)
O6—Gd1—O5	52.59 (6)	C4—C5—C9	119.0 (2)
O2—Gd1—O5	74.76 (6)	C7—C6—C4	121.4 (3)
O6—Gd1—O9	70.53 (6)	C7—C6—H6	119.3
O2—Gd1—O9	143.80 (6)	C4—C6—H6	119.3
O5—Gd1—O9	71.11 (6)	C6—C7—C8	121.4 (3)
O6—Gd1—N4	134.90 (6)	C6—C7—H7A	119.3
O2—Gd1—N4	72.04 (6)	C8—C7—H7A	119.3
O5—Gd1—N4	86.06 (6)	C10—C8—C9	118.0 (2)
O9—Gd1—N4	116.56 (6)	C10—C8—C7	123.3 (3)
O6—Gd1—O1	71.59 (6)	C9—C8—C7	118.7 (3)
O2—Gd1—O1	51.57 (5)	N2—C9—C8	122.0 (2)
O5—Gd1—O1	108.00 (6)	N2—C9—C5	118.1 (2)
O9—Gd1—O1	130.59 (6)	C8—C9—C5	119.9 (2)
N4—Gd1—O1	112.56 (6)	C11—C10—C8	119.8 (3)
O6—Gd1—N3	143.09 (6)	C11—C10—H10	120.1
O2—Gd1—N3	79.18 (6)	C8—C10—H10	120.1
O5—Gd1—N3	144.99 (6)	C10—C11—C12	118.5 (3)
O9—Gd1—N3	136.91 (6)	C10—C11—H11	120.7
N4—Gd1—N3	63.67 (6)	C12—C11—H11	120.7
O1—Gd1—N3	71.53 (6)	N2—C12—C11	124.4 (2)
O6—Gd1—N1	79.85 (6)	N2—C12—H12	117.8
O2—Gd1—N1	122.79 (6)	C11—C12—H12	117.8
O5—Gd1—N1	126.90 (6)	N3—C13—C14	123.1 (3)
O9—Gd1—N1	71.77 (6)	N3—C13—H13	118.5
N4—Gd1—N1	145.17 (7)	C14—C13—H13	118.5
O1—Gd1—N1	71.33 (6)	C15—C14—C13	119.3 (3)
N3—Gd1—N1	86.98 (6)	C15—C14—H14	120.3
O6—Gd1—O10	105.44 (6)	C13—C14—H14	120.3
O2—Gd1—O10	124.86 (6)	C14—C15—C16	120.3 (3)
O5—Gd1—O10	67.48 (6)	C14—C15—H15	119.8
O9—Gd1—O10	49.75 (6)	C16—C15—H15	119.8
N4—Gd1—O10	66.82 (6)	C15—C16—C17	116.6 (3)
O1—Gd1—O10	175.38 (6)	C15—C16—C21	124.0 (3)
N3—Gd1—O10	111.47 (6)	C17—C16—C21	119.4 (3)
N1—Gd1—O10	111.94 (6)	N3—C17—C16	123.3 (2)
O6—Gd1—N2	132.26 (6)	N3—C17—C18	117.6 (2)
O2—Gd1—N2	145.49 (6)	C16—C17—C18	119.0 (2)
O5—Gd1—N2	132.37 (6)	N4—C18—C19	122.5 (2)
O9—Gd1—N2	70.16 (6)	N4—C18—C17	117.4 (2)
N4—Gd1—N2	87.30 (6)	C19—C18—C17	120.2 (2)
O1—Gd1—N2	118.02 (6)	C22—C19—C18	117.6 (2)
N3—Gd1—N2	66.79 (6)	C22—C19—C20	123.8 (3)
N1—Gd1—N2	62.87 (7)	C18—C19—C20	118.6 (3)
O10—Gd1—N2	66.59 (6)	C21—C20—C19	121.7 (3)
O6—Gd1—C32	26.57 (6)	C21—C20—H20	119.1
O2—Gd1—C32	78.98 (6)	C19—C20—H20	119.1
O5—Gd1—C32	26.43 (6)	C20—C21—C16	120.8 (3)
O9—Gd1—C32	65.09 (7)	C20—C21—H21	119.6
N4—Gd1—C32	111.92 (7)	C16—C21—H21	119.6
O1—Gd1—C32	92.26 (7)	C23—C22—C19	120.0 (2)
N3—Gd1—C32	157.93 (7)	C23—C22—H22	120.0
N1—Gd1—C32	102.26 (7)	C19—C22—H22	120.0
O10—Gd1—C32	83.90 (7)	C22—C23—C24	119.0 (3)
N2—Gd1—C32	135.25 (7)	C22—C23—H23	120.5
O6—Gd1—C25	73.40 (6)	C24—C23—H23	120.5
O2—Gd1—C25	25.73 (6)	N4—C24—C23	123.6 (3)
O5—Gd1—C25	91.04 (6)	N4—C24—H24	118.2
O9—Gd1—C25	143.56 (7)	C23—C24—H24	118.2
N4—Gd1—C25	92.66 (7)	O1—C25—O2	119.6 (2)
O1—Gd1—C25	25.85 (6)	O1—C25—C26	120.8 (2)
N3—Gd1—C25	74.25 (6)	O2—C25—C26	119.5 (2)
N1—Gd1—C25	97.09 (7)	O1—C25—Gd1	61.84 (13)
O10—Gd1—C25	150.44 (7)	O2—C25—Gd1	57.80 (13)
N2—Gd1—C25	136.38 (6)	C26—C25—Gd1	176.71 (18)
C32—Gd1—C25	84.65 (7)	C31—C26—C27	117.2 (2)
C25—O1—Gd1	92.31 (15)	C31—C26—C25	121.4 (2)
C25—O2—Gd1	96.46 (15)	C27—C26—C25	121.4 (2)
C27—O3—H3	109.5	O3—C27—C28	117.7 (2)
C31—O4—H4	109.5	O3—C27—C26	121.5 (2)
C32—O5—Gd1	92.88 (15)	C28—C27—C26	120.8 (3)
C32—O6—Gd1	93.12 (15)	C29—C28—C27	119.5 (3)
C38—O7—H7	109.5	C29—C28—H28	120.2
C34—O8—H8	109.5	C27—C28—H28	120.2
N5—O9—Gd1	98.88 (13)	C30—C29—C28	121.9 (3)
N5—O10—Gd1	94.79 (14)	C30—C29—H29	119.0
C1—N1—C5	117.8 (2)	C28—C29—H29	119.0
C1—N1—Gd1	121.05 (18)	C29—C30—C31	119.3 (3)
C5—N1—Gd1	120.81 (15)	C29—C30—H30	120.3
C12—N2—C9	117.3 (2)	C31—C30—H30	120.3
C12—N2—Gd1	123.06 (17)	O4—C31—C30	117.9 (3)
C9—N2—Gd1	119.48 (16)	O4—C31—C26	121.0 (2)
C13—N3—C17	117.4 (2)	C30—C31—C26	121.1 (3)
C13—N3—Gd1	122.94 (17)	O5—C32—O6	119.6 (2)
C17—N3—Gd1	118.78 (15)	O5—C32—C33	120.5 (2)
C24—N4—C18	117.2 (2)	O6—C32—C33	119.9 (2)
C24—N4—Gd1	122.31 (16)	O5—C32—Gd1	60.70 (13)
C18—N4—Gd1	120.37 (15)	O6—C32—Gd1	60.30 (13)
O11—N5—O10	123.2 (3)	C33—C32—Gd1	166.12 (18)
O11—N5—O9	120.3 (2)	C34—C33—C38	118.3 (2)
O10—N5—O9	116.6 (2)	C34—C33—C32	121.3 (2)
O11—N5—Gd1	175.9 (2)	C38—C33—C32	120.4 (2)
O10—N5—Gd1	60.47 (12)	O8—C34—C35	117.9 (3)
O9—N5—Gd1	56.11 (11)	O8—C34—C33	120.9 (2)
N1—C1—C2	122.6 (3)	C35—C34—C33	121.1 (3)
N1—C1—H1	118.7	C36—C35—C34	118.5 (3)
C2—C1—H1	118.7	C36—C35—H35	120.7
C3—C2—C1	119.6 (3)	C34—C35—H35	120.7
C3—C2—H2	120.2	C35—C36—C37	123.1 (3)
C1—C2—H2	120.2	C35—C36—H36	118.5
C2—C3—C4	119.9 (3)	C37—C36—H36	118.5
C2—C3—H3A	120.0	C36—C37—C38	118.7 (3)
C4—C3—H3A	120.0	C36—C37—H37	120.7
C3—C4—C5	117.4 (3)	C38—C37—H37	120.7
C3—C4—C6	123.0 (3)	O7—C38—C37	117.1 (2)
C5—C4—C6	119.6 (3)	O7—C38—C33	122.6 (2)
N1—C5—C4	122.8 (2)	C37—C38—C33	120.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7···O5	0.82	1.87	2.592 (2)	147
O8—H8···O6	0.82	1.83	2.563 (3)	148
O4—H4···O1	0.82	1.86	2.585 (3)	147
O3—H3···O2	0.82	1.84	2.574 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7⋯O5	0.82	1.87	2.592 (2)	147
O8—H8⋯O6	0.82	1.83	2.563 (3)	148
O4—H4⋯O1	0.82	1.86	2.585 (3)	147
O3—H3⋯O2	0.82	1.84	2.574 (3)	148