{1,8-Bis[2-(2-oxidobenzyl-idene-amino)phen-oxy]-3,6-dioxaocta-ne}nitrato-praseodymium(III) trichloro-methane solvate.

In the title compound, [Pr(C(32)H(30)N(2)O(6))(NO(3))]·CHCl(3), the Pr(III) ion is ten-coordinated by eight O atoms and two N atoms from the acyclic crown-type Schiff base ligand and the bidentate nitrate group. The coordination polyhedron around Pr(III) is a distorted bicapped square anti-prism. The chloro-form solvent mol-ecule is not involved either in coordination to the Pr(III) center or in hydrogen bonding to the complex. The Pr-O(phenolate) bonds are significantly shorter than the Pr-O(ether) and Pr-O(nitrate) bonds, which suggests that the Pr-O(phenolate) bond is stronger than these other bonds. In the crystal structure, the acyclic crown-type Schiff base ligand wraps around the Pr(III) centre, forming a pseudo-ring.

Related literature

For general backgound, see: Wen et al. (2001 ▶); Liu et al. (2004 ▶). For related structures, see: Yu et al. (2006 ▶); Ding et al. (2007 ▶). For related literature, see: Si et al. (1994 ▶).

Experimental

Crystal data

[Pr(C32H30N2O6)(NO3)]·CHCl3

M = 860.87

Monoclinic,

a = 11.3454 (14) Å

b = 20.150 (2) Å

c = 15.4676 (17) Å

β = 100.585 (2)°

V = 3475.9 (7) Å3

Z = 4

Mo Kα radiation

μ = 1.69 mm−1

T = 298 (2) K

0.48 × 0.43 × 0.21 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.498, T max = 0.718

17233 measured reflections

6118 independent reflections

4284 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.083

S = 1.03

6118 reflections

442 parameters

H-atom parameters constrained

Δρmax = 1.44 e Å−3

Δρmin = −0.55 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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: publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808021259/wn2255sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021259/wn2255Isup2.hkl

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

[Pr(C32H30N2O6)(NO3)]·CHCl3	F000 = 1728
Mr = 860.87	Dx = 1.645 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
a = 11.3454 (14) Å	Cell parameters from 5219 reflections
b = 20.150 (2) Å	θ = 2.3–25.5º
c = 15.4676 (17) Å	µ = 1.69 mm−1
β = 100.585 (2)º	T = 298 (2) K
V = 3475.9 (7) Å3	Block, yellow
Z = 4	0.48 × 0.43 × 0.21 mm

Bruker SMART 1000 CCD diffractometer	6118 independent reflections
Radiation source: fine-focus sealed tube	4284 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.043
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.498, Tmax = 0.718	k = −23→20
17233 measured reflections	l = −16→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)] = 0.035	H-atom parameters constrained
wR(F2) = 0.083	w = 1/[σ2(Fo2) + (0.0368P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
6118 reflections	Δρmax = 1.44 e Å−3
442 parameters	Δρmin = −0.55 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
Pr1	0.84007 (2)	0.784583 (11)	0.158214 (16)	0.03001 (9)
Cl1	0.16296 (15)	0.61952 (9)	0.19132 (14)	0.0999 (6)
Cl2	0.23419 (17)	0.65708 (9)	0.03000 (13)	0.0984 (6)
Cl3	0.41044 (14)	0.64221 (10)	0.18791 (15)	0.1164 (7)
N1	0.6762 (3)	0.71096 (16)	0.0580 (2)	0.0339 (8)
N2	0.6852 (3)	0.76463 (17)	0.2664 (2)	0.0348 (9)
N3	1.1034 (3)	0.79143 (19)	0.2513 (3)	0.0436 (10)
C9	0.6446 (4)	0.5878 (2)	0.0482 (3)	0.0503 (13)
H9	0.5646	0.5918	0.0534	0.060*
O1	0.9051 (2)	0.69333 (14)	0.04725 (19)	0.0372 (7)
O2	0.9149 (3)	0.82509 (15)	0.01016 (19)	0.0409 (8)
O3	0.9091 (3)	0.91629 (14)	0.1443 (2)	0.0389 (7)
O4	0.8019 (2)	0.87638 (13)	0.2862 (2)	0.0376 (7)
O5	0.6794 (2)	0.84723 (13)	0.09646 (19)	0.0381 (7)
O6	0.8714 (2)	0.68515 (14)	0.2275 (2)	0.0394 (7)
O7	1.0201 (3)	0.80827 (17)	0.2899 (2)	0.0514 (9)
O8	1.0758 (3)	0.78130 (15)	0.1693 (2)	0.0462 (8)
O9	1.2050 (3)	0.7844 (2)	0.2900 (3)	0.0823 (13)
C1	0.9179 (4)	0.7150 (2)	−0.0398 (3)	0.0458 (12)
H1A	0.8394	0.7200	−0.0767	0.055*
H1B	0.9623	0.6821	−0.0666	0.055*
C2	0.9823 (4)	0.7793 (2)	−0.0330 (3)	0.0453 (12)
H2A	1.0627	0.7741	0.0008	0.054*
H2B	0.9882	0.7956	−0.0911	0.054*
C3	0.9633 (5)	0.8900 (2)	0.0084 (3)	0.0529 (14)
H3A	0.9595	0.9042	−0.0520	0.064*
H3B	1.0467	0.8902	0.0375	0.064*
C4	0.8932 (5)	0.9359 (2)	0.0539 (3)	0.0541 (14)
H4A	0.9210	0.9811	0.0495	0.065*
H4B	0.8090	0.9339	0.0270	0.065*
C5	0.8566 (4)	0.9631 (2)	0.1947 (3)	0.0454 (12)
H5A	0.7723	0.9690	0.1700	0.055*
H5B	0.8964	1.0057	0.1950	0.055*
C6	0.8715 (4)	0.9359 (2)	0.2860 (3)	0.0438 (12)
H6A	0.9554	0.9263	0.3080	0.053*
H6B	0.8454	0.9686	0.3245	0.053*
C7	0.8358 (4)	0.6361 (2)	0.0440 (3)	0.0375 (11)
C8	0.7160 (4)	0.6445 (2)	0.0490 (3)	0.0371 (11)
C10	0.6931 (5)	0.5260 (2)	0.0397 (4)	0.0599 (15)
H10	0.6453	0.4884	0.0384	0.072*
C11	0.8117 (5)	0.5196 (2)	0.0331 (4)	0.0609 (15)
H11	0.8438	0.4778	0.0270	0.073*
C12	0.8823 (5)	0.5746 (2)	0.0354 (3)	0.0495 (13)
H12	0.9626	0.5701	0.0311	0.059*
C13	0.5709 (4)	0.7263 (2)	0.0152 (3)	0.0386 (11)
H13	0.5275	0.6923	−0.0164	0.046*
C14	0.5133 (4)	0.7900 (2)	0.0109 (3)	0.0358 (10)
C15	0.5697 (4)	0.8475 (2)	0.0520 (3)	0.0351 (10)
C16	0.5031 (4)	0.9069 (2)	0.0427 (3)	0.0523 (13)
H16	0.5364	0.9450	0.0712	0.063*
C17	0.3912 (5)	0.9097 (3)	−0.0070 (4)	0.0635 (16)
H17	0.3502	0.9499	−0.0129	0.076*
C18	0.3374 (5)	0.8544 (3)	−0.0488 (4)	0.0695 (17)
H18	0.2606	0.8568	−0.0824	0.083*
C19	0.3990 (4)	0.7954 (3)	−0.0402 (3)	0.0525 (14)
H19	0.3635	0.7580	−0.0692	0.063*
C20	0.6820 (4)	0.8820 (2)	0.2903 (3)	0.0364 (11)
C21	0.6188 (4)	0.8227 (2)	0.2810 (3)	0.0376 (11)
C22	0.4985 (4)	0.8233 (3)	0.2833 (3)	0.0486 (13)
H22	0.4554	0.7838	0.2758	0.058*
C23	0.4404 (4)	0.8817 (3)	0.2966 (4)	0.0577 (15)
H23	0.3590	0.8817	0.2987	0.069*
C24	0.5048 (5)	0.9396 (3)	0.3066 (4)	0.0576 (15)
H24	0.4665	0.9790	0.3163	0.069*
C25	0.6248 (5)	0.9408 (2)	0.3027 (3)	0.0507 (13)
H25	0.6670	0.9806	0.3082	0.061*
C26	0.6611 (4)	0.7105 (2)	0.3046 (3)	0.0372 (11)
H26	0.6015	0.7130	0.3385	0.045*
C27	0.7169 (4)	0.6467 (2)	0.3000 (3)	0.0357 (11)
C28	0.8194 (4)	0.6370 (2)	0.2618 (3)	0.0348 (11)
C29	0.8640 (4)	0.5720 (2)	0.2616 (3)	0.0462 (12)
H29	0.9306	0.5641	0.2358	0.055*
C30	0.8129 (5)	0.5196 (2)	0.2980 (3)	0.0554 (14)
H30	0.8447	0.4772	0.2963	0.066*
C31	0.7142 (5)	0.5299 (3)	0.3372 (3)	0.0550 (14)
H31	0.6801	0.4947	0.3625	0.066*
C32	0.6671 (4)	0.5927 (2)	0.3383 (3)	0.0487 (13)
H32	0.6009	0.5996	0.3649	0.058*
C33	0.2640 (4)	0.6656 (3)	0.1447 (4)	0.0643 (16)
H33	0.2544	0.7125	0.1589	0.077*

	U11	U22	U33	U12	U13	U23
Pr1	0.02794 (14)	0.03197 (14)	0.02875 (14)	−0.00197 (11)	0.00155 (9)	0.00156 (12)
Cl1	0.0752 (12)	0.0960 (13)	0.1290 (17)	−0.0180 (10)	0.0202 (11)	0.0328 (12)
Cl2	0.1104 (14)	0.0852 (12)	0.1010 (15)	−0.0041 (10)	0.0232 (11)	−0.0036 (11)
Cl3	0.0498 (10)	0.1420 (17)	0.150 (2)	0.0073 (10)	−0.0020 (11)	−0.0466 (15)
N1	0.030 (2)	0.033 (2)	0.040 (2)	−0.0011 (17)	0.0089 (17)	−0.0020 (18)
N2	0.033 (2)	0.039 (2)	0.031 (2)	−0.0044 (17)	0.0038 (16)	0.0001 (17)
N3	0.026 (2)	0.053 (3)	0.048 (3)	0.0021 (19)	−0.0038 (19)	0.002 (2)
C9	0.050 (3)	0.048 (3)	0.052 (3)	−0.010 (3)	0.009 (3)	−0.010 (3)
O1	0.0364 (18)	0.0414 (18)	0.0343 (18)	−0.0057 (14)	0.0081 (14)	0.0002 (14)
O2	0.050 (2)	0.0399 (19)	0.0327 (19)	−0.0042 (15)	0.0083 (15)	0.0018 (15)
O3	0.0424 (19)	0.0337 (17)	0.041 (2)	−0.0066 (14)	0.0079 (15)	0.0002 (15)
O4	0.0342 (18)	0.0356 (18)	0.044 (2)	−0.0018 (14)	0.0087 (14)	0.0000 (15)
O5	0.0312 (17)	0.0356 (17)	0.0435 (19)	0.0013 (14)	−0.0037 (14)	−0.0021 (15)
O6	0.0354 (18)	0.0364 (17)	0.047 (2)	0.0035 (14)	0.0083 (15)	0.0129 (16)
O7	0.039 (2)	0.069 (2)	0.045 (2)	0.0021 (17)	0.0033 (16)	−0.0087 (18)
O8	0.0381 (18)	0.065 (2)	0.0342 (19)	0.0018 (16)	0.0036 (15)	−0.0025 (17)
O9	0.037 (2)	0.128 (4)	0.072 (3)	0.006 (2)	−0.015 (2)	−0.009 (3)
C1	0.061 (3)	0.052 (3)	0.025 (3)	0.000 (3)	0.010 (2)	−0.005 (2)
C2	0.060 (3)	0.043 (3)	0.036 (3)	−0.006 (2)	0.018 (2)	0.004 (2)
C3	0.079 (4)	0.042 (3)	0.040 (3)	−0.012 (3)	0.017 (3)	0.004 (2)
C4	0.087 (4)	0.032 (3)	0.046 (3)	−0.006 (3)	0.021 (3)	0.009 (2)
C5	0.053 (3)	0.028 (3)	0.054 (3)	−0.010 (2)	0.007 (3)	−0.007 (2)
C6	0.048 (3)	0.038 (3)	0.046 (3)	−0.008 (2)	0.009 (2)	−0.007 (2)
C7	0.043 (3)	0.036 (3)	0.035 (3)	−0.007 (2)	0.010 (2)	−0.002 (2)
C8	0.037 (3)	0.035 (3)	0.038 (3)	−0.004 (2)	0.002 (2)	−0.008 (2)
C10	0.077 (4)	0.039 (3)	0.066 (4)	−0.018 (3)	0.020 (3)	−0.010 (3)
C11	0.078 (4)	0.031 (3)	0.076 (4)	0.005 (3)	0.018 (3)	−0.008 (3)
C12	0.055 (3)	0.036 (3)	0.058 (4)	0.008 (2)	0.015 (3)	−0.008 (3)
C13	0.035 (3)	0.041 (3)	0.039 (3)	−0.011 (2)	0.005 (2)	−0.007 (2)
C14	0.031 (2)	0.043 (3)	0.033 (3)	−0.001 (2)	0.005 (2)	0.002 (2)
C15	0.032 (3)	0.045 (3)	0.030 (3)	0.003 (2)	0.008 (2)	0.003 (2)
C16	0.055 (3)	0.049 (3)	0.051 (3)	0.012 (3)	0.004 (3)	0.002 (3)
C17	0.049 (3)	0.071 (4)	0.065 (4)	0.026 (3)	−0.005 (3)	−0.003 (3)
C18	0.034 (3)	0.093 (5)	0.074 (4)	0.017 (3)	−0.008 (3)	0.004 (4)
C19	0.037 (3)	0.066 (4)	0.050 (3)	−0.003 (3)	−0.004 (2)	−0.002 (3)
C20	0.039 (3)	0.039 (3)	0.031 (3)	0.007 (2)	0.007 (2)	0.001 (2)
C21	0.038 (3)	0.041 (3)	0.033 (3)	0.003 (2)	0.006 (2)	−0.002 (2)
C22	0.035 (3)	0.054 (3)	0.056 (3)	−0.003 (2)	0.007 (2)	−0.002 (3)
C23	0.036 (3)	0.072 (4)	0.068 (4)	0.007 (3)	0.016 (3)	0.004 (3)
C24	0.056 (4)	0.056 (4)	0.062 (4)	0.019 (3)	0.014 (3)	−0.003 (3)
C25	0.055 (3)	0.046 (3)	0.052 (3)	0.000 (3)	0.011 (3)	0.000 (3)
C26	0.029 (2)	0.054 (3)	0.030 (2)	−0.010 (2)	0.0087 (19)	−0.009 (2)
C27	0.041 (3)	0.033 (3)	0.031 (3)	−0.008 (2)	0.002 (2)	−0.001 (2)
C28	0.033 (3)	0.036 (3)	0.032 (3)	−0.003 (2)	−0.002 (2)	0.005 (2)
C29	0.050 (3)	0.046 (3)	0.043 (3)	0.006 (2)	0.009 (2)	0.005 (2)
C30	0.068 (4)	0.042 (3)	0.052 (4)	0.000 (3)	−0.001 (3)	0.005 (3)
C31	0.073 (4)	0.044 (3)	0.045 (3)	−0.020 (3)	0.004 (3)	0.008 (3)
C32	0.050 (3)	0.051 (3)	0.044 (3)	−0.013 (3)	0.007 (2)	0.003 (3)
C33	0.046 (3)	0.048 (3)	0.100 (5)	−0.001 (3)	0.016 (3)	−0.010 (3)

Pr1—O6	2.269 (3)	C5—H5B	0.9700
Pr1—O5	2.278 (3)	C6—H6A	0.9700
Pr1—N1	2.646 (3)	C6—H6B	0.9700
Pr1—O8	2.649 (3)	C7—C12	1.363 (6)
Pr1—O7	2.649 (3)	C7—C8	1.386 (6)
Pr1—N2	2.670 (4)	C10—C11	1.374 (7)
Pr1—O1	2.708 (3)	C10—H10	0.9300
Pr1—O2	2.710 (3)	C11—C12	1.364 (6)
Pr1—O3	2.787 (3)	C11—H11	0.9300
Pr1—O4	2.801 (3)	C12—H12	0.9300
Cl1—C33	1.733 (5)	C13—C14	1.436 (6)
Cl2—C33	1.752 (6)	C13—H13	0.9300
Cl3—C33	1.738 (5)	C14—C19	1.393 (6)
N1—C13	1.293 (5)	C14—C15	1.415 (6)
N1—C8	1.429 (5)	C15—C16	1.408 (6)
N2—C26	1.293 (5)	C16—C17	1.360 (7)
N2—C21	1.432 (5)	C16—H16	0.9300
N3—O9	1.206 (5)	C17—C18	1.374 (7)
N3—O7	1.255 (4)	C17—H17	0.9300
N3—O8	1.266 (5)	C18—C19	1.372 (7)
C9—C10	1.378 (6)	C18—H18	0.9300
C9—C8	1.399 (6)	C19—H19	0.9300
C9—H9	0.9300	C20—C25	1.379 (6)
O1—C7	1.391 (5)	C20—C21	1.388 (6)
O1—C1	1.448 (5)	C21—C22	1.372 (6)
O2—C3	1.421 (5)	C22—C23	1.382 (6)
O2—C2	1.438 (5)	C22—H22	0.9300
O3—C5	1.422 (5)	C23—C24	1.371 (7)
O3—C4	1.432 (5)	C23—H23	0.9300
O4—C20	1.378 (5)	C24—C25	1.374 (6)
O4—C6	1.437 (5)	C24—H24	0.9300
O5—C15	1.306 (5)	C25—H25	0.9300
O6—C28	1.298 (5)	C26—C27	1.440 (6)
C1—C2	1.482 (6)	C26—H26	0.9300
C1—H1A	0.9700	C27—C32	1.407 (6)
C1—H1B	0.9700	C27—C28	1.411 (6)
C2—H2A	0.9700	C28—C29	1.405 (6)
C2—H2B	0.9700	C29—C30	1.373 (6)
C3—C4	1.480 (6)	C29—H29	0.9300
C3—H3A	0.9700	C30—C31	1.383 (7)
C3—H3B	0.9700	C30—H30	0.9300
C4—H4A	0.9700	C31—C32	1.375 (7)
C4—H4B	0.9700	C31—H31	0.9300
C5—C6	1.495 (6)	C32—H32	0.9300
C5—H5A	0.9700	C33—H33	0.9800
O6—Pr1—O5	136.97 (10)	C3—C4—H4B	110.1
O6—Pr1—N1	79.26 (11)	H4A—C4—H4B	108.4
O5—Pr1—N1	69.09 (10)	O3—C5—C6	106.8 (4)
O6—Pr1—O8	83.05 (10)	O3—C5—H5A	110.4
O5—Pr1—O8	139.60 (10)	C6—C5—H5A	110.4
N1—Pr1—O8	128.04 (10)	O3—C5—H5B	110.4
O6—Pr1—O7	76.36 (11)	C6—C5—H5B	110.4
O5—Pr1—O7	131.84 (10)	H5A—C5—H5B	108.6
N1—Pr1—O7	155.61 (11)	O4—C6—C5	109.9 (4)
O8—Pr1—O7	47.81 (10)	O4—C6—H6A	109.7
O6—Pr1—N2	68.58 (10)	C5—C6—H6A	109.7
O5—Pr1—N2	77.19 (11)	O4—C6—H6B	109.7
N1—Pr1—N2	79.07 (10)	C5—C6—H6B	109.7
O8—Pr1—N2	136.75 (10)	H6A—C6—H6B	108.2
O7—Pr1—N2	92.76 (10)	C12—C7—C8	121.2 (4)
O6—Pr1—O1	70.29 (10)	C12—C7—O1	122.1 (4)
O5—Pr1—O1	113.61 (10)	C8—C7—O1	116.8 (4)
N1—Pr1—O1	59.47 (9)	C7—C8—C9	118.2 (4)
O8—Pr1—O1	68.58 (9)	C7—C8—N1	116.8 (4)
O7—Pr1—O1	110.38 (9)	C9—C8—N1	125.0 (4)
N2—Pr1—O1	125.60 (9)	C11—C10—C9	120.3 (5)
O6—Pr1—O2	128.24 (10)	C11—C10—H10	119.8
O5—Pr1—O2	80.19 (10)	C9—C10—H10	119.8
N1—Pr1—O2	88.25 (10)	C12—C11—C10	120.1 (5)
O8—Pr1—O2	65.98 (9)	C12—C11—H11	119.9
O7—Pr1—O2	106.17 (10)	C10—C11—H11	119.9
N2—Pr1—O2	156.82 (10)	C7—C12—C11	120.3 (5)
O1—Pr1—O2	60.33 (8)	C7—C12—H12	119.9
O6—Pr1—O3	148.83 (10)	C11—C12—H12	119.9
O5—Pr1—O3	69.79 (9)	N1—C13—C14	127.4 (4)
N1—Pr1—O3	131.76 (10)	N1—C13—H13	116.3
O8—Pr1—O3	74.57 (9)	C14—C13—H13	116.3
O7—Pr1—O3	72.54 (10)	C19—C14—C15	119.2 (4)
N2—Pr1—O3	114.75 (10)	C19—C14—C13	117.6 (4)
O1—Pr1—O3	118.97 (8)	C15—C14—C13	123.1 (4)
O2—Pr1—O3	60.76 (9)	O5—C15—C16	119.9 (4)
O6—Pr1—O4	106.28 (10)	O5—C15—C14	122.8 (4)
O5—Pr1—O4	73.42 (9)	C16—C15—C14	117.4 (4)
N1—Pr1—O4	126.95 (9)	C17—C16—C15	121.4 (5)
O8—Pr1—O4	104.85 (9)	C17—C16—H16	119.3
O7—Pr1—O4	62.29 (9)	C15—C16—H16	119.3
N2—Pr1—O4	56.72 (9)	C16—C17—C18	121.4 (5)
O1—Pr1—O4	172.66 (8)	C16—C17—H17	119.3
O2—Pr1—O4	120.76 (8)	C18—C17—H17	119.3
O3—Pr1—O4	60.53 (8)	C19—C18—C17	118.8 (5)
C13—N1—C8	117.0 (4)	C19—C18—H18	120.6
C13—N1—Pr1	130.5 (3)	C17—C18—H18	120.6
C8—N1—Pr1	112.5 (2)	C18—C19—C14	121.8 (5)
C26—N2—C21	117.1 (4)	C18—C19—H19	119.1
C26—N2—Pr1	129.2 (3)	C14—C19—H19	119.1
C21—N2—Pr1	113.7 (3)	O4—C20—C25	124.8 (4)
O9—N3—O7	122.1 (4)	O4—C20—C21	114.8 (4)
O9—N3—O8	121.1 (4)	C25—C20—C21	120.4 (4)
O7—N3—O8	116.8 (4)	C22—C21—C20	119.1 (4)
C10—C9—C8	119.9 (5)	C22—C21—N2	124.5 (4)
C10—C9—H9	120.1	C20—C21—N2	116.3 (4)
C8—C9—H9	120.1	C21—C22—C23	121.0 (5)
C7—O1—C1	111.6 (3)	C21—C22—H22	119.5
C7—O1—Pr1	111.6 (2)	C23—C22—H22	119.5
C1—O1—Pr1	118.0 (2)	C24—C23—C22	118.9 (5)
C3—O2—C2	109.9 (3)	C24—C23—H23	120.6
C3—O2—Pr1	118.4 (3)	C22—C23—H23	120.6
C2—O2—Pr1	118.3 (2)	C23—C24—C25	121.4 (5)
C5—O3—C4	111.2 (3)	C23—C24—H24	119.3
C5—O3—Pr1	115.9 (2)	C25—C24—H24	119.3
C4—O3—Pr1	110.6 (2)	C24—C25—C20	119.1 (5)
C20—O4—C6	118.6 (3)	C24—C25—H25	120.4
C20—O4—Pr1	111.7 (2)	C20—C25—H25	120.4
C6—O4—Pr1	113.2 (2)	N2—C26—C27	126.7 (4)
C15—O5—Pr1	146.5 (3)	N2—C26—H26	116.6
C28—O6—Pr1	144.1 (3)	C27—C26—H26	116.6
N3—O7—Pr1	97.3 (3)	C32—C27—C28	119.7 (4)
N3—O8—Pr1	97.0 (2)	C32—C27—C26	117.1 (4)
O1—C1—C2	109.2 (4)	C28—C27—C26	123.2 (4)
O1—C1—H1A	109.8	O6—C28—C29	120.4 (4)
C2—C1—H1A	109.8	O6—C28—C27	122.6 (4)
O1—C1—H1B	109.8	C29—C28—C27	117.1 (4)
C2—C1—H1B	109.8	C30—C29—C28	122.4 (5)
H1A—C1—H1B	108.3	C30—C29—H29	118.8
O2—C2—C1	107.2 (4)	C28—C29—H29	118.8
O2—C2—H2A	110.3	C29—C30—C31	120.1 (5)
C1—C2—H2A	110.3	C29—C30—H30	120.0
O2—C2—H2B	110.3	C31—C30—H30	120.0
C1—C2—H2B	110.3	C32—C31—C30	119.4 (5)
H2A—C2—H2B	108.5	C32—C31—H31	120.3
O2—C3—C4	108.8 (4)	C30—C31—H31	120.3
O2—C3—H3A	109.9	C31—C32—C27	121.3 (5)
C4—C3—H3A	109.9	C31—C32—H32	119.4
O2—C3—H3B	109.9	C27—C32—H32	119.4
C4—C3—H3B	109.9	Cl1—C33—Cl3	110.7 (3)
H3A—C3—H3B	108.3	Cl1—C33—Cl2	110.4 (3)
O3—C4—C3	108.0 (4)	Cl3—C33—Cl2	110.9 (3)
O3—C4—H4A	110.1	Cl1—C33—H33	108.2
C3—C4—H4A	110.1	Cl3—C33—H33	108.2
O3—C4—H4B	110.1	Cl2—C33—H33	108.2

Pr1—O6	2.269 (3)
Pr1—O5	2.278 (3)
Pr1—N1	2.646 (3)
Pr1—O8	2.649 (3)
Pr1—O7	2.649 (3)
Pr1—N2	2.670 (4)
Pr1—O1	2.708 (3)
Pr1—O2	2.710 (3)
Pr1—O3	2.787 (3)
Pr1—O4	2.801 (3)

O6—Pr1—N1	79.26 (11)
O6—Pr1—O7	76.36 (11)
O8—Pr1—O7	47.81 (10)
O5—Pr1—N2	77.19 (11)
N1—Pr1—N2	79.07 (10)
O7—Pr1—N2	92.76 (10)
N1—Pr1—O1	59.47 (9)
O1—Pr1—O2	60.33 (8)
O2—Pr1—O3	60.76 (9)
O5—Pr1—O4	73.42 (9)
N2—Pr1—O4	56.72 (9)
O3—Pr1—O4	60.53 (8)