Nonaaqua­neodymium(III) trichloride bis­(1,3,5,7-tetra­aza­tricyclo­[3.3.1.1^3,7]deca­ne tetra­hydrate

The crystal structure of the title compound, [Nd(H₂O)₉]Cl₃·2C₆H₁₂N₄·4H₂O, is the first neodymium chloride complex with a cage adamanzane without any chloride ion in the lanthanide coordination sphere. The Nd-O distances range from 2.4425 (17) to 2.5635 (18) Å, and the neodymium ion has the coordination geometry of a capped square antiprism distorted toward a tricapped trigonal prism. The cations, [Nd(H₂O)₉]³⁺, are connected via hydrogen bonds to hexa­methyl­enetetra­mine mol­ecules, water mol­ecules and chloride ions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](N-C) = 0.004 Å
• H-atom completeness 97%
• Disorder in main residue
• R factor = 0.025
• wR factor = 0.069
• Data-to-parameter ratio = 20.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT411_ALERT_2_B Short Inter H...H Contact  H22A   ..  H22A    ..       2.08 Ang.

Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature         293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature ....        293
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Nd1
PLAT301_ALERT_3_C Main Residue  Disorder .........................       5.00 Perc.
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....       >O4'
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....       <O3'
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O4     -   H4B    ...       1.04 Ang.
PLAT411_ALERT_2_C Short Inter H...H Contact  H24A   ..  H24A    ..       2.12 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl3    ..  O4'     ..       3.17 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl4    ..  O3'     ..       3.23 Ang.

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C12 H50 Cl3 N8 Nd1 O13
            Atom count from the _atom_site data:  C12 H48 Cl3 N8 Nd1 O13
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    2
           From the CIF: _chemical_formula_sum  C12 H50 Cl3 N8 Nd O13
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         24.00     24.00    0.00
           H        100.00     96.00    4.00
           Cl         6.00      6.00    0.00
           N         16.00     16.00    0.00
           Nd         2.00      2.00    0.00
           O         26.00     26.00    0.00

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  14 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: KM-4 Software (Kuma, 1993); cell refinement: KM-4 Software; data reduction: DATAPROC (Gałdecki et al., 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1990b) ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Nonaaquaneodymium(III) trichloride bis(1,3,5,7-tetraazatricyclo[3.3.1.1^3,7]decane tetrahydrate

Crystal data

[Nd(H2O)9]Cl3·2C6H12N4·4H2O	Z = 2
Mr = 765.19	F(000) = 786
Triclinic, P1	Dx = 1.638 Mg m^−3
a = 9.8155 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.7230 (9) Å	Cell parameters from 99 reflections
c = 14.0699 (12) Å	θ = 2–25°
α = 85.964 (6)°	µ = 2.00 mm^−1
β = 76.178 (6)°	T = 293 K
γ = 80.879 (6)°	Prism, pale violet
V = 1551.3 (2) Å^3	0.56 × 0.28 × 0.24 mm

Data collection

Kuma KM-4 diffractometer	6791 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
Graphite monochromator	θmax = 27.6°, θmin = 1.8°
ω–2θ scans	h = −12→0
Absorption correction: numerical (X-RED; Stoe & Cie (1999)	k = −15→15
Tmin = 0.381, Tmax = 0.683	l = −18→17
7597 measured reflections	3 standard reflections every 100 reflections
7179 independent reflections	intensity decay: 43.7%

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)] = 0.025	Hydrogen site location: difference Fourier map
wR(F^2) = 0.069	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0398P)^2 + 1.1931P] where P = (Fo^2 + 2Fc^2)/3
7179 reflections	(Δ/σ)max = 0.002
354 parameters	Δρmax = 1.77 e Å^−3
0 restraints	Δρmin = −0.96 e Å^−3

Special details

Experimental. The crystal was measured in glass capillary

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Nd1	0.790374 (11)	0.298886 (10)	0.260505 (8)	0.02151 (5)
O1	0.8445 (2)	0.07789 (15)	0.25525 (15)	0.0368 (4)
H1A	0.8722	0.0575	0.1961	0.055*
H1B	0.8388	0.0230	0.3000	0.055*
O2	0.6298 (2)	0.41799 (18)	0.39545 (14)	0.0377 (4)
H2A	0.5772	0.4705	0.3706	0.057*
H2B	0.6391	0.4171	0.4542	0.057*
O3	0.7794 (2)	0.22498 (17)	0.10137 (13)	0.0340 (4)
H3A	0.6929	0.2268	0.1002	0.051*
H3B	0.8455	0.2033	0.0546	0.051*
O4	1.04509 (19)	0.23052 (16)	0.22012 (14)	0.0353 (4)
H4A	1.0780	0.1571	0.2280	0.053*
H4B	1.1298	0.2632	0.1736	0.053*
O5	0.59680 (19)	0.43631 (16)	0.20223 (14)	0.0348 (4)
H5A	0.5045	0.4440	0.2284	0.052*
H5B	0.5906	0.4989	0.1642	0.052*
O6	0.9177 (2)	0.44862 (18)	0.31345 (16)	0.0411 (5)
H6A	1.0129	0.4544	0.2973	0.062*
H6B	0.8949	0.5202	0.3309	0.062*
O7	0.8991 (2)	0.42546 (18)	0.11860 (15)	0.0398 (4)
H7A	0.9490	0.4815	0.1167	0.060*
H7B	0.9053	0.4155	0.0547	0.060*
O8	0.8352 (2)	0.21832 (18)	0.41702 (13)	0.0362 (4)
H8A	0.9185	0.2254	0.4327	0.054*
H8B	0.7951	0.1797	0.4725	0.054*
O9	0.5737 (2)	0.20749 (17)	0.30905 (15)	0.0383 (4)
H9A	0.5249	0.2325	0.3639	0.057*
H9B	0.5741	0.1369	0.2867	0.057*
C10	0.0834 (3)	0.1184 (2)	0.5537 (2)	0.0371 (6)
H10A	−0.0057	0.1204	0.6007	0.056*
H10B	0.0993	0.0489	0.5179	0.056*
N10	0.1975 (3)	0.1163 (2)	0.60564 (17)	0.0355 (5)
C11	0.1725 (3)	0.2244 (3)	0.6586 (2)	0.0416 (6)
H11A	0.0844	0.2279	0.7069	0.062*
H11B	0.2468	0.2243	0.6923	0.062*
N11	0.1674 (3)	0.3275 (2)	0.59270 (18)	0.0362 (5)
C12	0.3028 (3)	0.3192 (3)	0.5190 (2)	0.0397 (6)
H12A	0.3010	0.3855	0.4749	0.059*
H12B	0.3785	0.3199	0.5511	0.059*
N12	0.3305 (2)	0.2136 (2)	0.46262 (17)	0.0348 (5)
C13	0.2136 (3)	0.2136 (3)	0.41398 (19)	0.0354 (5)
H13A	0.2300	0.1446	0.3774	0.053*
H13B	0.2109	0.2787	0.3688	0.053*
N13	0.0760 (2)	0.2192 (2)	0.48541 (16)	0.0325 (4)
C14	0.0531 (3)	0.3246 (3)	0.5410 (2)	0.0403 (6)
H14A	−0.0362	0.3290	0.5879	0.060*
H14B	0.0488	0.3909	0.4970	0.060*
C15	0.3326 (3)	0.1138 (2)	0.5317 (2)	0.0385 (6)
H15A	0.4083	0.1134	0.5642	0.058*
H15B	0.3508	0.0439	0.4962	0.058*
C20	0.2881 (3)	0.1661 (3)	1.0044 (2)	0.0382 (6)
H20A	0.2069	0.1767	0.9761	0.057*
H20B	0.2882	0.0947	1.0423	0.057*
N20	0.2770 (2)	0.26219 (18)	1.06917 (16)	0.0312 (4)
C21	0.4028 (3)	0.2441 (2)	1.11123 (19)	0.0325 (5)
H21A	0.4047	0.1728	1.1492	0.049*
H21B	0.3970	0.3057	1.1543	0.049*
N21	0.5347 (2)	0.24053 (18)	1.03395 (17)	0.0309 (4)
C22	0.5288 (3)	0.3494 (2)	0.9754 (2)	0.0354 (6)
H22A	0.5245	0.4125	1.0166	0.053*
H22B	0.6141	0.3475	0.9246	0.053*
N22	0.4061 (3)	0.3695 (2)	0.93100 (17)	0.0351 (5)
C23	0.4147 (4)	0.2702 (3)	0.8692 (2)	0.0455 (7)
H23A	0.3342	0.2812	0.8402	0.068*
H23B	0.4985	0.2676	0.8171	0.068*
N23	0.4185 (3)	0.1594 (2)	0.92546 (18)	0.0386 (5)
C24	0.5417 (3)	0.1457 (2)	0.9701 (2)	0.0374 (6)
H24A	0.5457	0.0740	1.0074	0.056*
H24B	0.6269	0.1425	0.9192	0.056*
C25	0.2769 (3)	0.3708 (2)	1.0106 (2)	0.0367 (6)
H25A	0.2702	0.4338	1.0523	0.055*
H25B	0.1951	0.3835	0.9828	0.055*
Cl1	0.66506 (9)	0.14196 (7)	0.62208 (6)	0.04897 (18)
Cl2	0.75514 (9)	0.50367 (8)	0.73817 (7)	0.0574 (2)
O91	0.1863 (3)	1.0053 (2)	0.2211 (2)	0.0630 (7)
H91A	0.2236	0.9623	0.2600	0.094*
H91B	0.1235	0.9749	0.1940	0.094*
O92	0.6069 (3)	0.40931 (19)	0.59876 (17)	0.0496 (5)
H92A	0.6484	0.4241	0.6313	0.074*
H92B	0.6231	0.3511	0.6068	0.074*
O93	0.5541 (3)	−0.0017 (2)	0.23620 (18)	0.0577 (6)
H93A	0.5043	−0.0410	0.2738	0.087*
H93B	0.5788	−0.0376	0.1823	0.087*
Cl3	−0.0204 (2)	0.1166 (2)	0.90897 (15)	0.0525 (6)	0.532 (6)
O4'	−0.0573 (6)	0.3904 (7)	0.8993 (4)	0.0470 (12)	0.532 (6)
Cl4	0.0294 (3)	0.6623 (3)	0.08671 (15)	0.0458 (7)	0.468 (6)
O3'	0.0072 (12)	0.9386 (12)	0.0993 (6)	0.091 (3)	0.468 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Nd1	0.02086 (7)	0.02285 (7)	0.01997 (7)	−0.00352 (4)	−0.00322 (4)	0.00064 (4)
O1	0.0466 (11)	0.0229 (8)	0.0365 (10)	−0.0040 (8)	−0.0025 (8)	0.0021 (7)
O2	0.0366 (10)	0.0441 (11)	0.0291 (9)	0.0084 (8)	−0.0083 (8)	−0.0094 (8)
O3	0.0307 (9)	0.0431 (10)	0.0284 (9)	−0.0016 (8)	−0.0077 (7)	−0.0075 (8)
O4	0.0238 (8)	0.0300 (9)	0.0448 (11)	−0.0002 (7)	0.0017 (7)	0.0053 (8)
O5	0.0290 (9)	0.0352 (9)	0.0349 (9)	0.0018 (7)	−0.0043 (7)	0.0089 (8)
O6	0.0355 (10)	0.0362 (10)	0.0520 (12)	−0.0133 (8)	−0.0015 (9)	−0.0170 (9)
O7	0.0476 (11)	0.0390 (10)	0.0344 (10)	−0.0186 (9)	−0.0084 (8)	0.0119 (8)
O8	0.0322 (9)	0.0511 (11)	0.0267 (9)	−0.0094 (8)	−0.0103 (7)	0.0085 (8)
O9	0.0331 (9)	0.0362 (10)	0.0419 (10)	−0.0142 (8)	0.0073 (8)	−0.0120 (8)
C10	0.0350 (13)	0.0372 (14)	0.0417 (15)	−0.0147 (11)	−0.0092 (11)	0.0037 (11)
N10	0.0402 (12)	0.0329 (11)	0.0351 (11)	−0.0068 (9)	−0.0130 (9)	0.0054 (9)
C11	0.0491 (16)	0.0492 (17)	0.0267 (13)	−0.0092 (13)	−0.0076 (11)	−0.0031 (11)
N11	0.0382 (12)	0.0320 (11)	0.0376 (12)	−0.0041 (9)	−0.0053 (9)	−0.0104 (9)
C12	0.0425 (15)	0.0355 (14)	0.0429 (15)	−0.0167 (12)	−0.0048 (12)	−0.0074 (11)
N12	0.0284 (10)	0.0394 (12)	0.0348 (11)	−0.0086 (9)	0.0004 (9)	−0.0078 (9)
C13	0.0397 (14)	0.0417 (14)	0.0257 (12)	−0.0095 (11)	−0.0067 (10)	−0.0026 (10)
N13	0.0298 (11)	0.0370 (11)	0.0324 (11)	−0.0039 (9)	−0.0112 (9)	−0.0012 (9)
C14	0.0359 (14)	0.0340 (13)	0.0482 (16)	0.0049 (11)	−0.0101 (12)	−0.0041 (12)
C15	0.0328 (13)	0.0354 (14)	0.0486 (16)	0.0021 (11)	−0.0146 (12)	−0.0084 (12)
C20	0.0336 (13)	0.0372 (14)	0.0459 (15)	−0.0110 (11)	−0.0094 (11)	−0.0026 (12)
N20	0.0279 (10)	0.0283 (10)	0.0336 (11)	−0.0012 (8)	−0.0025 (8)	0.0021 (8)
C21	0.0375 (13)	0.0285 (12)	0.0310 (12)	−0.0025 (10)	−0.0090 (10)	0.0008 (9)
N21	0.0298 (10)	0.0236 (10)	0.0399 (12)	−0.0030 (8)	−0.0103 (9)	0.0000 (8)
C22	0.0377 (14)	0.0252 (12)	0.0435 (15)	−0.0093 (10)	−0.0081 (11)	0.0035 (10)
N22	0.0403 (12)	0.0302 (11)	0.0331 (11)	−0.0056 (9)	−0.0069 (9)	0.0074 (9)
C23	0.0578 (19)	0.0526 (18)	0.0273 (13)	−0.0112 (14)	−0.0094 (12)	−0.0035 (12)
N23	0.0439 (13)	0.0360 (12)	0.0361 (12)	−0.0104 (10)	−0.0036 (10)	−0.0117 (10)
C24	0.0329 (13)	0.0251 (12)	0.0496 (16)	0.0003 (10)	−0.0011 (11)	−0.0093 (11)
C25	0.0355 (13)	0.0296 (12)	0.0399 (14)	0.0043 (10)	−0.0065 (11)	0.0052 (11)
Cl1	0.0586 (5)	0.0446 (4)	0.0417 (4)	−0.0146 (3)	−0.0049 (3)	0.0051 (3)
Cl2	0.0465 (4)	0.0577 (5)	0.0658 (5)	−0.0139 (4)	0.0013 (4)	−0.0218 (4)
O91	0.0612 (16)	0.0461 (13)	0.0816 (19)	0.0007 (11)	−0.0223 (14)	−0.0013 (13)
O92	0.0569 (14)	0.0369 (11)	0.0507 (13)	0.0086 (10)	−0.0139 (11)	−0.0034 (9)
O93	0.0765 (17)	0.0504 (13)	0.0498 (13)	−0.0293 (12)	−0.0052 (12)	−0.0121 (11)
Cl3	0.0583 (10)	0.0511 (12)	0.0452 (9)	−0.0010 (8)	−0.0058 (7)	−0.0201 (8)
O4'	0.057 (3)	0.033 (3)	0.052 (3)	−0.010 (2)	−0.016 (2)	0.002 (2)
Cl4	0.0539 (12)	0.0489 (15)	0.0356 (9)	−0.0153 (10)	−0.0067 (7)	−0.0020 (9)
O3'	0.150 (9)	0.071 (6)	0.048 (4)	−0.007 (6)	−0.020 (4)	−0.014 (4)

Geometric parameters (Å, º)

Nd1—O4	2.4425 (17)	N12—C15	1.468 (4)
Nd1—O8	2.4442 (18)	N12—C13	1.471 (3)
Nd1—O9	2.4624 (18)	C13—N13	1.473 (3)
Nd1—O3	2.4887 (18)	C13—H13A	0.9600
Nd1—O2	2.5069 (18)	C13—H13B	0.9600
Nd1—O7	2.5285 (18)	N13—C14	1.468 (4)
Nd1—O5	2.5428 (18)	C14—H14A	0.9600
Nd1—O6	2.5542 (18)	C14—H14B	0.9600
Nd1—O1	2.5635 (18)	C15—H15A	0.9600
O1—H1A	0.8500	C15—H15B	0.9600
O1—H1B	0.8667	C20—N20	1.472 (4)
O2—H2A	0.8501	C20—N23	1.477 (4)
O2—H2B	0.8529	C20—H20A	0.9600
O3—H3A	0.8501	C20—H20B	0.9600
O3—H3B	0.8281	N20—C25	1.468 (3)
O4—H4A	0.8789	N20—C21	1.473 (3)
O4—H4B	1.0352	C21—N21	1.475 (3)
O5—H5A	0.8849	C21—H21A	0.9600
O5—H5B	0.8805	C21—H21B	0.9600
O6—H6A	0.9190	N21—C24	1.461 (3)
O6—H6B	0.8706	N21—C22	1.470 (3)
O7—H7A	0.8745	C22—N22	1.465 (4)
O7—H7B	0.9013	C22—H22A	0.9600
O8—H8A	0.9130	C22—H22B	0.9600
O8—H8B	0.9105	N22—C25	1.477 (3)
O9—H9A	0.8500	N22—C23	1.481 (4)
O9—H9B	0.9040	C23—N23	1.473 (4)
C10—N10	1.472 (3)	C23—H23A	0.9600
C10—N13	1.473 (4)	C23—H23B	0.9600
C10—H10A	0.9600	N23—C24	1.473 (4)
C10—H10B	0.9600	C24—H24A	0.9600
N10—C11	1.473 (4)	C24—H24B	0.9600
N10—C15	1.474 (4)	C25—H25A	0.9600
C11—N11	1.473 (4)	C25—H25B	0.9600
C11—H11A	0.9600	O91—H91A	0.8279
C11—H11B	0.9600	O91—H91B	0.9241
N11—C12	1.472 (4)	O92—H92A	0.7263
N11—C14	1.481 (4)	O92—H92B	0.6832
C12—N12	1.471 (3)	O93—H93A	0.8030
C12—H12A	0.9600	O93—H93B	0.8583
C12—H12B	0.9600
O4—Nd1—O8	76.98 (6)	N12—C12—N11	112.1 (2)
O4—Nd1—O9	135.64 (7)	N12—C12—H12A	109.2
O8—Nd1—O9	84.62 (7)	N11—C12—H12A	109.2
O4—Nd1—O3	88.06 (7)	N12—C12—H12B	109.2
O8—Nd1—O3	137.46 (7)	N11—C12—H12B	109.2
O9—Nd1—O3	78.84 (6)	H12A—C12—H12B	107.9
O4—Nd1—O2	133.31 (7)	C15—N12—C13	108.6 (2)
O8—Nd1—O2	71.32 (7)	C15—N12—C12	108.0 (2)
O9—Nd1—O2	74.48 (7)	C13—N12—C12	108.5 (2)
O3—Nd1—O2	138.05 (6)	N12—C13—N13	111.4 (2)
O4—Nd1—O7	73.24 (7)	N12—C13—H13A	109.3
O8—Nd1—O7	139.09 (7)	N13—C13—H13A	109.3
O9—Nd1—O7	136.20 (7)	N12—C13—H13B	109.3
O3—Nd1—O7	68.89 (7)	N13—C13—H13B	109.3
O2—Nd1—O7	111.25 (7)	H13A—C13—H13B	108.0
O4—Nd1—O5	142.78 (6)	C14—N13—C13	108.6 (2)
O8—Nd1—O5	137.04 (6)	C14—N13—C10	108.6 (2)
O9—Nd1—O5	73.48 (7)	C13—N13—C10	108.1 (2)
O3—Nd1—O5	74.30 (6)	N13—C14—N11	111.9 (2)
O2—Nd1—O5	67.44 (6)	N13—C14—H14A	109.2
O7—Nd1—O5	69.88 (6)	N11—C14—H14A	109.2
O4—Nd1—O6	71.35 (7)	N13—C14—H14B	109.2
O8—Nd1—O6	76.79 (7)	N11—C14—H14B	109.2
O9—Nd1—O6	142.38 (6)	H14A—C14—H14B	107.9
O3—Nd1—O6	135.52 (7)	N12—C15—N10	112.0 (2)
O2—Nd1—O6	68.69 (7)	N12—C15—H15A	109.2
O7—Nd1—O6	67.54 (7)	N10—C15—H15A	109.2
O5—Nd1—O6	98.57 (7)	N12—C15—H15B	109.2
O4—Nd1—O1	68.03 (6)	N10—C15—H15B	109.2
O8—Nd1—O1	70.10 (7)	H15A—C15—H15B	107.9
O9—Nd1—O1	67.80 (7)	N20—C20—N23	111.5 (2)
O3—Nd1—O1	67.37 (6)	N20—C20—H20A	109.3
O2—Nd1—O1	127.53 (7)	N23—C20—H20A	109.3
O7—Nd1—O1	121.22 (7)	N20—C20—H20B	109.3
O5—Nd1—O1	129.38 (7)	N23—C20—H20B	109.3
O6—Nd1—O1	131.95 (7)	H20A—C20—H20B	108.0
Nd1—O1—H1A	109.8	C25—N20—C20	108.8 (2)
Nd1—O1—H1B	133.4	C25—N20—C21	108.6 (2)
H1A—O1—H1B	116.8	C20—N20—C21	108.2 (2)
Nd1—O2—H2A	108.8	N20—C21—N21	111.3 (2)
Nd1—O2—H2B	125.6	N20—C21—H21A	109.4
H2A—O2—H2B	124.1	N21—C21—H21A	109.4
Nd1—O3—H3A	108.7	N20—C21—H21B	109.4
Nd1—O3—H3B	128.7	N21—C21—H21B	109.4
H3A—O3—H3B	122.6	H21A—C21—H21B	108.0
Nd1—O4—H4A	120.9	C24—N21—C22	108.3 (2)
Nd1—O4—H4B	132.5	C24—N21—C21	108.3 (2)
H4A—O4—H4B	103.5	C22—N21—C21	108.7 (2)
Nd1—O5—H5A	126.9	N22—C22—N21	112.2 (2)
Nd1—O5—H5B	137.5	N22—C22—H22A	109.2
H5A—O5—H5B	94.2	N21—C22—H22A	109.2
Nd1—O6—H6A	128.6	N22—C22—H22B	109.2
Nd1—O6—H6B	135.6	N21—C22—H22B	109.2
H6A—O6—H6B	92.2	H22A—C22—H22B	107.9
Nd1—O7—H7A	130.7	C22—N22—C25	108.0 (2)
Nd1—O7—H7B	126.2	C22—N22—C23	107.9 (2)
H7A—O7—H7B	102.7	C25—N22—C23	107.9 (2)
Nd1—O8—H8A	119.6	N23—C23—N22	112.2 (2)
Nd1—O8—H8B	142.0	N23—C23—H23A	109.2
H8A—O8—H8B	98.4	N22—C23—H23A	109.2
Nd1—O9—H9A	109.5	N23—C23—H23B	109.2
Nd1—O9—H9B	119.2	N22—C23—H23B	109.2
H9A—O9—H9B	124.8	H23A—C23—H23B	107.9
N10—C10—N13	111.9 (2)	C24—N23—C23	107.9 (2)
N10—C10—H10A	109.2	C24—N23—C20	108.6 (2)
N13—C10—H10A	109.2	C23—N23—C20	107.8 (2)
N10—C10—H10B	109.2	N21—C24—N23	112.0 (2)
N13—C10—H10B	109.2	N21—C24—H24A	109.2
H10A—C10—H10B	107.9	N23—C24—H24A	109.2
C10—N10—C11	108.4 (2)	N21—C24—H24B	109.2
C10—N10—C15	108.0 (2)	N23—C24—H24B	109.2
C11—N10—C15	107.9 (2)	H24A—C24—H24B	107.9
N11—C11—N10	112.2 (2)	N20—C25—N22	111.9 (2)
N11—C11—H11A	109.2	N20—C25—H25A	109.2
N10—C11—H11A	109.2	N22—C25—H25A	109.2
N11—C11—H11B	109.2	N20—C25—H25B	109.2
N10—C11—H11B	109.2	N22—C25—H25B	109.2
H11A—C11—H11B	107.9	H25A—C25—H25B	107.9
C12—N11—C11	108.0 (2)	H91A—O91—H91B	116.3
C12—N11—C14	107.9 (2)	H92A—O92—H92B	94.0
C11—N11—C14	108.0 (2)	H93A—O93—H93B	105.4

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···Cl3^i	0.85	2.63	3.333 (3)	141
O1—H1A···O3′^ii	0.85	2.09	2.835 (11)	146
O1—H1B···N10^i	0.87	2.05	2.910 (3)	170
O2—H2A···O92^iii	0.85	2.08	2.818 (3)	144
O2—H2A···O5	0.85	2.39	2.803 (3)	111
O2—H2B···O92	0.85	1.98	2.811 (3)	165
O3—H3A···N21^iv	0.85	1.97	2.762 (3)	154
O3—H3B···Cl3^v	0.83	2.35	3.155 (3)	163
O3—H3B···Cl4^vi	0.83	2.64	3.192 (3)	126
O4—H4A···O91^ii	0.88	1.92	2.781 (3)	167
O4—H4B···N20^v	1.04	1.80	2.771 (3)	155
O5—H5A···Cl2^iii	0.88	2.46	3.326 (2)	165
O5—H5B···N22^iii	0.88	1.97	2.846 (3)	174
O6—H6A···Cl2^vii	0.92	2.34	3.248 (2)	172
O6—H6B···N11^iii	0.87	2.08	2.932 (3)	166
O7—H7A···O4′^iii	0.87	1.94	2.817 (6)	175
O7—H7B···O4′^v	0.90	2.16	3.060 (6)	174
O7—H7A···Cl4^viii	0.87	2.35	3.198 (3)	162
O7—H7B···Cl4^vi	0.90	2.16	3.019 (3)	159
O8—H8A···N13^viii	0.91	1.86	2.758 (3)	168
O8—H8B···Cl1	0.91	2.24	3.118 (2)	162
O9—H9A···N12	0.85	2.11	2.806 (3)	139
O9—H9B···O93	0.90	1.87	2.774 (3)	173
O91—H91A···Cl1^iii	0.83	2.37	3.190 (3)	174
O91—H91B···Cl3^ix	0.92	2.35	3.252 (4)	164
O91—H91B···O3′	0.92	2.05	2.950 (10)	163
O92—H92A···Cl2	0.73	2.34	3.061 (3)	170
O92—H92B···Cl1	0.68	2.42	3.104 (2)	174
O93—H93A···Cl1^i	0.80	2.35	3.150 (3)	173
O93—H93B···N23^i	0.86	2.15	2.968 (3)	160
C20—H20A···Cl3	0.96	2.82	3.731 (4)	158
C21—H21B···Cl2^x	0.96	2.80	3.673 (3)	151

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x+1, y−1, z; (iii) −x+1, −y+1, −z+1; (iv) x, y, z−1; (v) x+1, y, z−1; (vi) −x+1, −y+1, −z; (vii) −x+2, −y+1, −z+1; (viii) x+1, y, z; (ix) −x, −y+1, −z+1; (x) −x+1, −y+1, −z+2.