Bis(μ-3-nitro-benzene-1,2-dicarboxyl-ato)-κ(4)O(1),O(2):O(1),O(1');κ(4)O(1),O(1'):O(1),O(2)-bis-[triaqua-(6-carb-oxy-2-nitro-benzoato-κ(2)O(1),O(6))neodymium(III)] dihydrate.

The title complex, [Nd(2)(C(8)H(3)NO(6))(2)(C(8)H(4)NO(6))(2)(H(2)O)(6)]·2H(2)O, consists of dimeric units related by an inversion center. The Nd(III) atom is nine-coordinated by three O atoms from water mol-ecules and six from carboxyl-ate atoms. The 1,2-dicarboxylate acid molecules are in a single and double deprotonation stage and exhibit two coord-in-ation modes, viz. μ(2)-(κ(4), O(1): O(2): O(2): O(3)) and μ(1)-(κ(2), O(2): O(3)), which are responsible for the dimeric structure framework. The dimeric structure is then assembled into a three-dimensional supramolecular framework via O-H⋯O hydrogen bonds.

Related literature

For the isotypic La compound, see: Xiong & Qi (2007 ▶).

Experimental

Crystal data

[Nd2 2(C8H3NO6)2(C8H4NO6)(H2O)6]·2H2O

M = 1271.08

Triclinic,

a = 8.1460 (7) Å

b = 8.8090 (9) Å

c = 15.1670 (13) Å

α = 100.434 (1)°

β = 91.106 (1)°

γ = 104.482 (2)°

V = 1033.96 (16) Å3

Z = 1

Mo Kα radiation

μ = 2.60 mm−1

T = 298 K

0.16 × 0.14 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.681, T max = 0.781

5316 measured reflections

3618 independent reflections

3196 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.076

S = 1.03

3618 reflections

317 parameters

H-atom parameters constrained

Δρmax = 1.51 e Å−3

Δρmin = −0.88 e Å−3

Data collection: SMART (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 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812042754/vn2055sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042754/vn2055Isup2.hkl

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

[Nd2(C8H3NO6)2(C8H4NO6)2(H2O)6]·2H2O	Z = 1
Mr = 1271.08	F(000) = 626
Triclinic, P1	Dx = 2.041 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1460 (7) Å	Cell parameters from 2861 reflections
b = 8.8090 (9) Å	θ = 2.6–27.9°
c = 15.1670 (13) Å	µ = 2.60 mm−1
α = 100.434 (1)°	T = 298 K
β = 91.106 (1)°	Block, purple
γ = 104.482 (2)°	0.16 × 0.14 × 0.10 mm
V = 1033.96 (16) Å3

Bruker SMART CCD area-detector diffractometer	3618 independent reflections
Radiation source: fine-focus sealed tube	3196 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
phi and ω scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −9→8
Tmin = 0.681, Tmax = 0.781	k = −10→10
5316 measured reflections	l = −14→18

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0341P)2] where P = (Fo2 + 2Fc2)/3
3618 reflections	(Δ/σ)max = 0.001
317 parameters	Δρmax = 1.51 e Å−3
0 restraints	Δρmin = −0.88 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
Nd1	0.34954 (3)	0.61211 (3)	0.432565 (17)	0.02109 (10)
N1	0.6299 (5)	0.3586 (5)	0.0945 (3)	0.0357 (11)
N2	1.0429 (5)	0.8971 (5)	0.8325 (3)	0.0338 (10)
O1	0.2534 (4)	0.6797 (4)	0.2912 (2)	0.0323 (8)
O2	0.0666 (4)	0.6809 (4)	0.1849 (2)	0.0387 (9)
H2	0.0399	0.7439	0.2253	0.058*
O3	0.5209 (4)	0.5333 (4)	0.3102 (2)	0.0239 (7)
O4	0.6217 (4)	0.7219 (4)	0.2293 (2)	0.0317 (8)
O5	0.7245 (5)	0.4265 (5)	0.1614 (3)	0.0525 (11)
O6	0.6688 (5)	0.2711 (5)	0.0317 (3)	0.0594 (12)
O7	0.4497 (4)	0.8304 (4)	0.5729 (2)	0.0313 (8)
O8	0.5879 (4)	0.6447 (3)	0.5528 (2)	0.0222 (7)
O9	1.0001 (4)	0.8529 (4)	0.6082 (2)	0.0354 (9)
O10	0.8932 (4)	0.6062 (4)	0.6320 (2)	0.0282 (8)
O11	1.1186 (5)	0.8219 (6)	0.7825 (3)	0.0686 (15)
O12	1.1035 (5)	0.9742 (6)	0.9051 (3)	0.0666 (14)
O13	0.2084 (4)	0.5262 (4)	0.5708 (2)	0.0362 (9)
H13C	0.2752	0.5118	0.6104	0.043*
H13D	0.1227	0.5482	0.5960	0.043*
O14	0.5560 (4)	0.8539 (4)	0.4017 (2)	0.0363 (9)
H14B	0.5211	0.9371	0.4185	0.044*
H14C	0.5732	0.8444	0.3461	0.044*
O15	0.1355 (4)	0.7563 (4)	0.4572 (2)	0.0374 (9)
H15C	0.0946	0.7860	0.5066	0.045*
H15D	0.0798	0.7770	0.4150	0.045*
O16	0.9404 (4)	0.8298 (4)	0.3189 (2)	0.0382 (9)
H16C	0.8423	0.7975	0.2915	0.046*
H16D	0.9577	0.9285	0.3414	0.046*
C1	0.1920 (6)	0.6321 (6)	0.2148 (3)	0.0278 (11)
C2	0.5315 (6)	0.5899 (5)	0.2390 (3)	0.0249 (11)
C3	0.2498 (6)	0.5176 (6)	0.1470 (3)	0.0264 (11)
C4	0.4139 (6)	0.4937 (5)	0.1582 (3)	0.0244 (11)
C5	0.4606 (6)	0.3880 (5)	0.0893 (3)	0.0292 (11)
C6	0.3539 (7)	0.3078 (6)	0.0136 (4)	0.0395 (14)
H6	0.3899	0.2386	−0.0312	0.047*
C7	0.1944 (7)	0.3323 (6)	0.0059 (4)	0.0397 (14)
H7	0.1217	0.2795	−0.0444	0.048*
C8	0.1426 (7)	0.4342 (6)	0.0721 (3)	0.0334 (12)
H8	0.0335	0.4480	0.0669	0.040*
C9	0.5563 (6)	0.7666 (5)	0.6009 (3)	0.0225 (10)
C10	0.9095 (6)	0.7554 (6)	0.6468 (3)	0.0258 (11)
C11	0.6390 (6)	0.8337 (5)	0.6931 (3)	0.0221 (10)
C12	0.8033 (6)	0.8239 (5)	0.7179 (3)	0.0208 (10)
C13	0.8675 (6)	0.8954 (5)	0.8048 (3)	0.0244 (11)
C14	0.7784 (6)	0.9698 (6)	0.8671 (3)	0.0314 (12)
H14	0.8264	1.0151	0.9250	0.038*
C15	0.6166 (7)	0.9762 (6)	0.8425 (4)	0.0354 (13)
H15	0.5539	1.0254	0.8838	0.042*
C16	0.5485 (6)	0.9089 (5)	0.7558 (3)	0.0271 (11)
H16	0.4399	0.9141	0.7391	0.032*

	U11	U22	U33	U12	U13	U23
Nd1	0.02379 (15)	0.02005 (14)	0.01938 (16)	0.00804 (10)	−0.00171 (10)	0.00071 (11)
N1	0.037 (3)	0.030 (2)	0.040 (3)	0.009 (2)	0.014 (2)	0.002 (2)
N2	0.033 (3)	0.031 (2)	0.032 (3)	0.005 (2)	−0.009 (2)	−0.002 (2)
O1	0.038 (2)	0.045 (2)	0.0184 (19)	0.0203 (17)	−0.0029 (15)	0.0049 (17)
O2	0.038 (2)	0.046 (2)	0.034 (2)	0.0232 (18)	−0.0095 (17)	−0.0026 (18)
O3	0.0257 (18)	0.0293 (17)	0.0194 (18)	0.0123 (14)	0.0027 (14)	0.0043 (15)
O4	0.0310 (19)	0.0286 (18)	0.032 (2)	0.0014 (15)	0.0011 (15)	0.0071 (16)
O5	0.040 (2)	0.063 (3)	0.053 (3)	0.025 (2)	−0.002 (2)	−0.009 (2)
O6	0.060 (3)	0.069 (3)	0.048 (3)	0.031 (2)	0.017 (2)	−0.013 (2)
O7	0.037 (2)	0.0268 (17)	0.031 (2)	0.0167 (15)	−0.0086 (16)	−0.0019 (16)
O8	0.0302 (18)	0.0204 (16)	0.0161 (17)	0.0115 (14)	−0.0017 (13)	−0.0032 (14)
O9	0.039 (2)	0.0296 (18)	0.037 (2)	0.0069 (16)	0.0173 (17)	0.0048 (17)
O10	0.0263 (18)	0.0225 (17)	0.033 (2)	0.0081 (14)	−0.0031 (15)	−0.0031 (15)
O11	0.045 (3)	0.101 (4)	0.056 (3)	0.039 (3)	−0.016 (2)	−0.020 (3)
O12	0.056 (3)	0.078 (3)	0.052 (3)	0.025 (2)	−0.032 (2)	−0.029 (3)
O13	0.031 (2)	0.050 (2)	0.034 (2)	0.0165 (17)	0.0089 (16)	0.0136 (18)
O14	0.047 (2)	0.0233 (17)	0.039 (2)	0.0116 (16)	0.0102 (17)	0.0047 (16)
O15	0.047 (2)	0.051 (2)	0.024 (2)	0.0328 (19)	0.0043 (16)	0.0055 (18)
O16	0.042 (2)	0.0252 (18)	0.046 (2)	0.0133 (16)	−0.0067 (18)	−0.0017 (17)
C1	0.027 (3)	0.029 (3)	0.028 (3)	0.008 (2)	0.002 (2)	0.009 (2)
C2	0.024 (3)	0.028 (3)	0.023 (3)	0.013 (2)	0.003 (2)	−0.003 (2)
C3	0.028 (3)	0.030 (3)	0.023 (3)	0.007 (2)	0.000 (2)	0.009 (2)
C4	0.027 (3)	0.024 (2)	0.022 (3)	0.005 (2)	0.003 (2)	0.006 (2)
C5	0.039 (3)	0.024 (2)	0.026 (3)	0.008 (2)	0.005 (2)	0.009 (2)
C6	0.061 (4)	0.030 (3)	0.024 (3)	0.008 (3)	0.003 (3)	−0.001 (2)
C7	0.049 (4)	0.037 (3)	0.027 (3)	0.006 (3)	−0.015 (3)	0.000 (3)
C8	0.041 (3)	0.030 (3)	0.029 (3)	0.011 (2)	−0.011 (2)	0.003 (2)
C9	0.022 (2)	0.022 (2)	0.021 (3)	0.002 (2)	0.001 (2)	0.002 (2)
C10	0.022 (3)	0.031 (3)	0.021 (3)	0.010 (2)	−0.005 (2)	−0.005 (2)
C11	0.026 (3)	0.020 (2)	0.020 (3)	0.0053 (19)	0.002 (2)	0.002 (2)
C12	0.024 (2)	0.017 (2)	0.019 (3)	0.0029 (19)	−0.0009 (19)	0.001 (2)
C13	0.030 (3)	0.019 (2)	0.023 (3)	0.006 (2)	−0.001 (2)	0.001 (2)
C14	0.041 (3)	0.030 (3)	0.017 (3)	0.004 (2)	0.001 (2)	−0.002 (2)
C15	0.047 (3)	0.029 (3)	0.028 (3)	0.013 (2)	0.010 (2)	−0.004 (2)
C16	0.026 (3)	0.026 (2)	0.029 (3)	0.011 (2)	0.004 (2)	0.000 (2)

Nd1—O1	2.489 (3)	O14—H14B	0.8500
Nd1—O3	2.447 (3)	O14—H14C	0.8500
Nd1—O7	2.561 (3)	O15—H15C	0.8500
Nd1—O8	2.564 (3)	O15—H15D	0.8500
Nd1—O8i	2.486 (3)	O16—H16C	0.8500
Nd1—O10i	2.431 (3)	O16—H16D	0.8499
Nd1—O13	2.554 (3)	C1—C3	1.475 (7)
Nd1—O14	2.487 (3)	C2—C4	1.520 (6)
Nd1—O15	2.398 (3)	C3—C8	1.390 (6)
N1—O6	1.212 (5)	C3—C4	1.416 (6)
N1—O5	1.225 (6)	C4—C5	1.394 (7)
N1—C5	1.469 (6)	C5—C6	1.391 (7)
N2—O11	1.197 (6)	C6—C7	1.376 (8)
N2—O12	1.208 (5)	C6—H6	0.9300
N2—C13	1.477 (6)	C7—C8	1.368 (7)
O1—C1	1.211 (6)	C7—H7	0.9300
O2—C1	1.306 (6)	C8—H8	0.9300
O2—H2	0.8200	C9—C11	1.491 (6)
O3—C2	1.265 (6)	C10—C12	1.528 (6)
O4—C2	1.246 (5)	C11—C16	1.389 (6)
O7—C9	1.252 (5)	C11—C12	1.411 (6)
O8—C9	1.270 (5)	C12—C13	1.384 (6)
O8—Nd1i	2.486 (3)	C13—C14	1.375 (7)
O9—C10	1.228 (6)	C14—C15	1.381 (7)
O10—C10	1.265 (5)	C14—H14	0.9300
O10—Nd1i	2.431 (3)	C15—C16	1.383 (7)
O13—H13C	0.8500	C15—H15	0.9300
O13—H13D	0.8500	C16—H16	0.9300
O15—Nd1—O10i	82.46 (11)	Nd1—O14—H14C	111.0
O15—Nd1—O3	137.86 (11)	H14B—O14—H14C	109.2
O10i—Nd1—O3	90.90 (11)	Nd1—O15—H15C	127.9
O15—Nd1—O8i	142.35 (11)	Nd1—O15—H15D	123.5
O10i—Nd1—O8i	71.22 (10)	H15C—O15—H15D	108.3
O3—Nd1—O8i	70.52 (10)	H16C—O16—H16D	108.4
O15—Nd1—O14	90.69 (12)	O1—C1—O2	121.7 (5)
O10i—Nd1—O14	143.71 (12)	O1—C1—C3	124.5 (4)
O3—Nd1—O14	70.66 (11)	O2—C1—C3	113.8 (4)
O8i—Nd1—O14	126.35 (11)	O4—C2—O3	126.7 (4)
O15—Nd1—O1	68.22 (11)	O4—C2—C4	115.8 (4)
O10i—Nd1—O1	73.83 (11)	O3—C2—C4	117.3 (4)
O3—Nd1—O1	69.96 (10)	C8—C3—C4	120.4 (5)
O8i—Nd1—O1	125.78 (10)	C8—C3—C1	119.6 (4)
O14—Nd1—O1	70.56 (12)	C4—C3—C1	120.1 (4)
O15—Nd1—O13	75.73 (11)	C5—C4—C3	116.2 (4)
O10i—Nd1—O13	76.95 (11)	C5—C4—C2	124.1 (4)
O3—Nd1—O13	143.02 (11)	C3—C4—C2	119.6 (4)
O8i—Nd1—O13	72.49 (10)	C6—C5—C4	123.0 (5)
O14—Nd1—O13	135.72 (11)	C6—C5—N1	117.1 (5)
O1—Nd1—O13	135.80 (11)	C4—C5—N1	119.9 (4)
O15—Nd1—O7	72.57 (11)	C7—C6—C5	119.0 (5)
O10i—Nd1—O7	141.54 (11)	C7—C6—H6	120.5
O3—Nd1—O7	127.18 (11)	C5—C6—H6	120.5
O8i—Nd1—O7	112.88 (10)	C8—C7—C6	120.1 (5)
O14—Nd1—O7	66.79 (11)	C8—C7—H7	120.0
O1—Nd1—O7	120.33 (11)	C6—C7—H7	120.0
O13—Nd1—O7	68.93 (11)	C7—C8—C3	121.3 (5)
O15—Nd1—O8	121.59 (10)	C7—C8—H8	119.4
O10i—Nd1—O8	133.76 (10)	C3—C8—H8	119.4
O3—Nd1—O8	92.65 (10)	O7—C9—O8	120.4 (4)
O8i—Nd1—O8	66.76 (11)	O7—C9—C11	118.2 (4)
O14—Nd1—O8	79.62 (11)	O8—C9—C11	121.4 (4)
O1—Nd1—O8	149.00 (11)	O9—C10—O10	126.6 (4)
O13—Nd1—O8	72.89 (11)	O9—C10—C12	115.4 (4)
O7—Nd1—O8	50.55 (9)	O10—C10—C12	117.9 (4)
O6—N1—O5	124.0 (5)	C16—C11—C12	119.8 (4)
O6—N1—C5	118.1 (5)	C16—C11—C9	117.6 (4)
O5—N1—C5	117.9 (4)	C12—C11—C9	122.6 (4)
O11—N2—O12	122.9 (5)	C13—C12—C11	116.8 (4)
O11—N2—C13	118.9 (4)	C13—C12—C10	122.9 (4)
O12—N2—C13	118.2 (4)	C11—C12—C10	119.8 (4)
C1—O1—Nd1	147.6 (3)	C14—C13—C12	123.6 (4)
C1—O2—H2	109.5	C14—C13—N2	117.4 (4)
C2—O3—Nd1	122.9 (3)	C12—C13—N2	119.0 (4)
C9—O7—Nd1	94.6 (3)	C13—C14—C15	119.0 (5)
C9—O8—Nd1i	140.4 (3)	C13—C14—H14	120.5
C9—O8—Nd1	94.0 (3)	C15—C14—H14	120.5
Nd1i—O8—Nd1	113.24 (11)	C14—C15—C16	119.4 (5)
C10—O10—Nd1i	129.9 (3)	C14—C15—H15	120.3
Nd1—O13—H13C	115.0	C16—C15—H15	120.3
Nd1—O13—H13D	130.1	C15—C16—C11	121.4 (5)
H13C—O13—H13D	108.7	C15—C16—H16	119.3
Nd1—O14—H14B	111.1	C11—C16—H16	119.3
O15—Nd1—O1—C1	−122.1 (6)	O4—C2—C4—C5	88.0 (6)
O10i—Nd1—O1—C1	−33.8 (6)	O3—C2—C4—C5	−96.1 (6)
O3—Nd1—O1—C1	63.2 (6)	O4—C2—C4—C3	−87.7 (5)
O8i—Nd1—O1—C1	17.7 (6)	O3—C2—C4—C3	88.2 (5)
O14—Nd1—O1—C1	139.0 (6)	C3—C4—C5—C6	−0.6 (7)
O13—Nd1—O1—C1	−84.4 (6)	C2—C4—C5—C6	−176.4 (5)
O7—Nd1—O1—C1	−174.6 (6)	C3—C4—C5—N1	178.8 (4)
O8—Nd1—O1—C1	122.5 (6)	C2—C4—C5—N1	3.0 (7)
O15—Nd1—O3—C2	12.2 (4)	O6—N1—C5—C6	2.4 (7)
O10i—Nd1—O3—C2	91.9 (3)	O5—N1—C5—C6	−179.0 (5)
O8i—Nd1—O3—C2	161.6 (3)	O6—N1—C5—C4	−177.0 (5)
O14—Nd1—O3—C2	−56.2 (3)	O5—N1—C5—C4	1.6 (7)
O1—Nd1—O3—C2	19.5 (3)	C4—C5—C6—C7	−0.4 (8)
O13—Nd1—O3—C2	161.1 (3)	N1—C5—C6—C7	−179.8 (5)
O7—Nd1—O3—C2	−94.0 (3)	C5—C6—C7—C8	0.0 (8)
O8—Nd1—O3—C2	−134.2 (3)	C6—C7—C8—C3	1.5 (8)
O15—Nd1—O7—C9	161.9 (3)	C4—C3—C8—C7	−2.5 (8)
O10i—Nd1—O7—C9	109.9 (3)	C1—C3—C8—C7	177.1 (5)
O3—Nd1—O7—C9	−60.6 (3)	Nd1—O7—C9—O8	7.1 (4)
O8i—Nd1—O7—C9	21.7 (3)	Nd1—O7—C9—C11	−170.4 (3)
O14—Nd1—O7—C9	−99.6 (3)	Nd1i—O8—C9—O7	−141.9 (4)
O1—Nd1—O7—C9	−147.5 (3)	Nd1—O8—C9—O7	−7.1 (4)
O13—Nd1—O7—C9	80.8 (3)	Nd1i—O8—C9—C11	35.6 (7)
O8—Nd1—O7—C9	−3.9 (2)	Nd1—O8—C9—C11	170.4 (4)
O15—Nd1—O8—C9	−12.1 (3)	Nd1i—O10—C10—O9	−111.5 (5)
O10i—Nd1—O8—C9	−124.2 (3)	Nd1i—O10—C10—C12	66.6 (5)
O3—Nd1—O8—C9	142.1 (3)	O7—C9—C11—C16	27.8 (6)
O8i—Nd1—O8—C9	−150.5 (3)	O8—C9—C11—C16	−149.7 (4)
O14—Nd1—O8—C9	72.3 (3)	O7—C9—C11—C12	−151.8 (4)
O1—Nd1—O8—C9	88.1 (3)	O8—C9—C11—C12	30.7 (7)
O13—Nd1—O8—C9	−72.6 (3)	C16—C11—C12—C13	−1.6 (6)
O7—Nd1—O8—C9	3.9 (2)	C9—C11—C12—C13	178.0 (4)
O15—Nd1—O8—Nd1i	138.38 (13)	C16—C11—C12—C10	−174.2 (4)
O10i—Nd1—O8—Nd1i	26.3 (2)	C9—C11—C12—C10	5.4 (7)
O3—Nd1—O8—Nd1i	−67.47 (13)	O9—C10—C12—C13	−82.4 (6)
O8i—Nd1—O8—Nd1i	0.0	O10—C10—C12—C13	99.3 (5)
O14—Nd1—O8—Nd1i	−137.26 (14)	O9—C10—C12—C11	89.8 (5)
O1—Nd1—O8—Nd1i	−121.39 (18)	O10—C10—C12—C11	−88.6 (5)
O13—Nd1—O8—Nd1i	77.86 (13)	C11—C12—C13—C14	1.8 (7)
O7—Nd1—O8—Nd1i	154.34 (19)	C10—C12—C13—C14	174.1 (5)
Nd1—O1—C1—O2	131.8 (5)	C11—C12—C13—N2	−176.4 (4)
Nd1—O1—C1—C3	−48.8 (9)	C10—C12—C13—N2	−4.0 (7)
Nd1—O3—C2—O4	79.5 (5)	O11—N2—C13—C14	173.7 (5)
Nd1—O3—C2—C4	−95.9 (4)	O12—N2—C13—C14	−6.0 (7)
O1—C1—C3—C8	160.5 (5)	O11—N2—C13—C12	−8.0 (7)
O2—C1—C3—C8	−20.1 (7)	O12—N2—C13—C12	172.3 (5)
O1—C1—C3—C4	−19.9 (7)	C12—C13—C14—C15	−0.8 (8)
O2—C1—C3—C4	159.5 (4)	N2—C13—C14—C15	177.4 (4)
C8—C3—C4—C5	2.0 (7)	C13—C14—C15—C16	−0.4 (8)
C1—C3—C4—C5	−177.6 (4)	C14—C15—C16—C11	0.5 (8)
C8—C3—C4—C2	178.0 (4)	C12—C11—C16—C15	0.5 (7)
C1—C3—C4—C2	−1.6 (7)	C9—C11—C16—C15	−179.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O16ii	0.82	1.79	2.588 (4)	163
O13—H13C···O3i	0.85	2.19	3.026 (5)	169
O13—H13D···O10ii	0.85	2.12	2.952 (5)	168
O14—H14B···O7iii	0.85	1.98	2.750 (5)	150
O14—H14C···O4	0.85	2.00	2.782 (4)	152
O15—H15C···O9ii	0.85	1.81	2.654 (4)	177
O15—H15D···O16ii	0.85	2.02	2.867 (5)	177
O16—H16C···O4	0.85	1.92	2.767 (5)	179
O16—H16D···O9iv	0.85	1.88	2.730 (5)	179

Table 1

Selected bond lengths (Å)

Nd1—O1	2.489 (3)
Nd1—O3	2.447 (3)
Nd1—O7	2.561 (3)
Nd1—O8	2.564 (3)
Nd1—O8i	2.486 (3)
Nd1—O10i	2.431 (3)
Nd1—O13	2.554 (3)
Nd1—O14	2.487 (3)
Nd1—O15	2.398 (3)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O16ii	0.82	1.79	2.588 (4)	163
O13—H13C⋯O3i	0.85	2.19	3.026 (5)	169
O13—H13D⋯O10ii	0.85	2.12	2.952 (5)	168
O14—H14B⋯O7iii	0.85	1.98	2.750 (5)	150
O14—H14C⋯O4	0.85	2.00	2.782 (4)	152
O15—H15C⋯O9ii	0.85	1.81	2.654 (4)	177
O15—H15D⋯O16ii	0.85	2.02	2.867 (5)	177
O16—H16C⋯O4	0.85	1.92	2.767 (5)	179
O16—H16D⋯O9iv	0.85	1.88	2.730 (5)	179

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .