Heptaaqua­[tetra­chloro­phthalato(2–)]praseodymium(III) tetra­chloro­phthalate(–) tetra­chloro­phthalic acid monohydrate

The title complex, [Pr(C₈Cl₄O₄)(H₂O)₇](C₈HCl₄O₄)·C₈H₂Cl₄O₄·H₂O, has been synthesized and structurally characterized. The praseodymium(III) ion is coordinated by an O atom of a tetra­chloro­phthalate ligand and seven O atoms of water mol­ecules. The mol­ecular packing is reinforced by an extensive network of O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.023
• wR factor = 0.057
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor       O6     -   H6B    ...          ?
PLAT431_ALERT_2_B Short Inter HL..A Contact  Cl1    ..  O12     ..       2.96 Ang.

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Pr1
PLAT417_ALERT_2_C Short Inter D-H..H-D       H8A    ..  H20A    ..       2.13 Ang.

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

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

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Heptaaqua[tetrachlorophthalato(2-)]praseodymium(III) tetrachlorophthalate(-) tetrachlorophthalic acid monohydrate

Crystal data

[Pr(C8Cl4O4)(H2O)7](C8HCl4O4)·C8H2Cl4O4·H2O	Z = 2
Mr = 1193.70	F(000) = 1172
Triclinic, P1	Dx = 2.013 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9395 (5) Å	Cell parameters from 5233 reflections
b = 16.2519 (13) Å	θ = 2.2–27.7°
c = 19.1287 (15) Å	µ = 2.13 mm^−1
α = 67.382 (1)°	T = 293 K
β = 86.524 (1)°	Block, green
γ = 81.535 (1)°	0.42 × 0.28 × 0.16 mm
V = 1969.7 (3) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	6883 independent reflections
Radiation source: fine-focus sealed tube	6066 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −8→7
Tmin = 0.414, Tmax = 0.711	k = −17→19
10795 measured reflections	l = −21→22

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.023	H-atom parameters constrained
wR(F^2) = 0.057	w = 1/[σ^2(Fo^2) + (0.0273P)^2 + 0.4655P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.002
6883 reflections	Δρmax = 0.54 e Å^−3
518 parameters	Δρmin = −0.50 e Å^−3
25 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0061 (3)

Special details

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
Pr1	0.54110 (2)	0.810379 (11)	0.998899 (9)	0.02423 (7)
Cl1	−0.27029 (11)	1.14687 (6)	0.70352 (5)	0.03740 (19)
Cl2	−0.09581 (15)	1.12265 (7)	0.55798 (5)	0.0537 (3)
Cl3	0.32663 (16)	1.02705 (8)	0.55900 (5)	0.0576 (3)
Cl4	0.56384 (12)	0.94367 (6)	0.70921 (5)	0.0431 (2)
Cl5	0.14172 (13)	0.63315 (6)	0.60883 (5)	0.0421 (2)
Cl6	0.24556 (12)	0.64055 (6)	0.44581 (5)	0.0416 (2)
Cl7	0.31776 (12)	0.46329 (7)	0.41562 (4)	0.0413 (2)
Cl8	0.28820 (13)	0.28063 (6)	0.54719 (5)	0.0439 (2)
Cl9	−0.19141 (14)	0.20388 (6)	0.23031 (6)	0.0504 (2)
Cl10	0.05139 (15)	0.13782 (6)	0.37742 (5)	0.0504 (2)
Cl11	0.40599 (16)	0.23268 (7)	0.38238 (5)	0.0535 (3)
Cl12	0.48896 (13)	0.40602 (6)	0.24507 (5)	0.0438 (2)
O1	0.3839 (4)	0.88026 (18)	0.87633 (13)	0.0537 (7)
O2	0.4132 (4)	1.0131 (2)	0.87671 (14)	0.0540 (7)
O3	−0.0467 (3)	0.99290 (14)	0.89599 (11)	0.0310 (5)
O4	−0.0406 (3)	1.13994 (13)	0.84721 (11)	0.0297 (5)
O5	0.8258 (3)	0.83604 (16)	0.91097 (14)	0.0437 (6)
H5A	0.8787	0.8840	0.8956	0.065*
H5B	0.8991	0.7878	0.9145	0.065*
O6	0.5337 (4)	0.70388 (15)	0.93461 (14)	0.0441 (6)
H6A	0.5943	0.6512	0.9434	0.066*
H6B	0.4522	0.7261	0.8950	0.066*
O7	0.8092 (4)	0.68732 (19)	1.06421 (14)	0.0565 (7)
H7A	0.9123	0.6785	1.0403	0.085*
H7B	0.7998	0.6511	1.1098	0.085*
O8	0.3804 (4)	0.68244 (18)	1.08421 (16)	0.0621 (8)
H8A	0.3630	0.6704	1.1313	0.093*
H8B	0.3384	0.6477	1.0667	0.093*
O9	0.5185 (4)	0.81127 (17)	1.12982 (13)	0.0444 (6)
H9A	0.4666	0.7707	1.1654	0.067*
H9B	0.5405	0.8560	1.1393	0.067*
O10	0.2092 (3)	0.87621 (17)	1.01591 (13)	0.0417 (6)
H10A	0.1667	0.8640	1.0609	0.063*
H10B	0.1253	0.9017	0.9809	0.063*
O11	0.6984 (3)	0.92930 (15)	1.00936 (12)	0.0333 (5)
H11A	0.6604	0.9508	1.0427	0.050*
H11B	0.7608	0.9628	0.9722	0.050*
O12	0.3227 (3)	0.22452 (16)	0.71844 (14)	0.0424 (6)
O13	0.0242 (3)	0.28455 (15)	0.73729 (13)	0.0366 (5)
H13	0.0217	0.2352	0.7717	0.055*
O14	0.2471 (3)	0.42153 (18)	0.77746 (13)	0.0448 (6)
O15	−0.0601 (3)	0.47471 (16)	0.74075 (12)	0.0341 (5)
H15	−0.0760	0.4698	0.7849	0.051*
O16	0.1635 (3)	0.54179 (14)	0.12264 (12)	0.0303 (5)
O17	0.2886 (3)	0.46216 (14)	0.05436 (11)	0.0313 (5)
O18	−0.1692 (4)	0.44973 (15)	0.08293 (12)	0.0378 (5)
H18	−0.2042	0.4692	0.0387	0.057*
O19	−0.0785 (4)	0.32278 (16)	0.06411 (13)	0.0424 (6)
C1	−0.0143 (4)	1.0642 (2)	0.84322 (16)	0.0228 (6)
C2	0.0691 (4)	1.05582 (19)	0.77073 (16)	0.0215 (6)
C3	−0.0379 (4)	1.0915 (2)	0.70466 (17)	0.0264 (7)
C4	0.0398 (5)	1.0814 (2)	0.63917 (17)	0.0304 (7)
C5	0.2272 (5)	1.0370 (2)	0.64015 (17)	0.0311 (7)
C6	0.3333 (4)	1.0000 (2)	0.70718 (17)	0.0257 (7)
C7	0.2535 (4)	1.00799 (19)	0.77301 (16)	0.0224 (6)
C8	0.3599 (4)	0.9641 (2)	0.84727 (18)	0.0324 (8)
C9	0.1210 (4)	0.4488 (2)	0.72980 (16)	0.0242 (6)
C10	0.1668 (4)	0.4538 (2)	0.65050 (16)	0.0232 (6)
C11	0.1804 (4)	0.5357 (2)	0.59125 (17)	0.0261 (7)
C12	0.2280 (4)	0.5391 (2)	0.51856 (17)	0.0273 (7)
C13	0.2626 (4)	0.4600 (2)	0.50535 (16)	0.0272 (7)
C14	0.2521 (4)	0.3775 (2)	0.56480 (17)	0.0262 (7)
C15	0.2045 (4)	0.3739 (2)	0.63771 (16)	0.0229 (6)
C16	0.1927 (4)	0.2858 (2)	0.70175 (17)	0.0251 (7)
C17	−0.0786 (4)	0.3685 (2)	0.10117 (17)	0.0273 (7)
C18	0.0334 (4)	0.33665 (19)	0.17400 (16)	0.0237 (6)
C19	−0.0042 (5)	0.2603 (2)	0.23492 (17)	0.0291 (7)
C20	0.1071 (5)	0.2289 (2)	0.30072 (17)	0.0316 (7)
C21	0.2616 (5)	0.2730 (2)	0.30373 (17)	0.0311 (7)
C22	0.2967 (4)	0.3504 (2)	0.24271 (17)	0.0281 (7)
C23	0.1823 (4)	0.38345 (19)	0.17852 (16)	0.0234 (6)
C24	0.2144 (4)	0.4695 (2)	0.11321 (16)	0.0244 (6)
O20	0.3702 (4)	0.65970 (18)	0.23256 (16)	0.0558 (7)
H20A	0.4690	0.6194	0.2442	0.084*
H20B	0.2671	0.6457	0.2581	0.084*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pr1	0.02665 (11)	0.02521 (11)	0.02297 (11)	−0.00529 (7)	0.00172 (6)	−0.01113 (8)
Cl1	0.0307 (4)	0.0401 (5)	0.0363 (5)	0.0072 (4)	−0.0056 (3)	−0.0123 (4)
Cl2	0.0663 (6)	0.0625 (6)	0.0252 (5)	0.0115 (5)	−0.0151 (4)	−0.0141 (5)
Cl3	0.0727 (7)	0.0709 (7)	0.0241 (5)	0.0110 (5)	0.0087 (4)	−0.0211 (5)
Cl4	0.0370 (5)	0.0475 (5)	0.0445 (5)	0.0095 (4)	0.0061 (4)	−0.0237 (4)
Cl5	0.0520 (5)	0.0254 (4)	0.0476 (5)	−0.0032 (4)	0.0021 (4)	−0.0136 (4)
Cl6	0.0368 (5)	0.0376 (5)	0.0334 (5)	−0.0058 (4)	0.0002 (3)	0.0054 (4)
Cl7	0.0362 (4)	0.0652 (6)	0.0225 (4)	−0.0099 (4)	0.0036 (3)	−0.0163 (4)
Cl8	0.0557 (5)	0.0429 (5)	0.0442 (5)	−0.0113 (4)	0.0109 (4)	−0.0289 (4)
Cl9	0.0562 (6)	0.0385 (5)	0.0517 (6)	−0.0235 (4)	0.0008 (4)	−0.0061 (5)
Cl10	0.0733 (7)	0.0351 (5)	0.0273 (5)	−0.0039 (5)	0.0109 (4)	0.0023 (4)
Cl11	0.0751 (7)	0.0495 (6)	0.0279 (5)	0.0075 (5)	−0.0215 (4)	−0.0085 (4)
Cl12	0.0402 (5)	0.0452 (5)	0.0483 (5)	−0.0053 (4)	−0.0136 (4)	−0.0186 (4)
O1	0.0761 (19)	0.0407 (16)	0.0278 (13)	0.0284 (14)	−0.0076 (12)	−0.0069 (12)
O2	0.0475 (15)	0.093 (2)	0.0396 (15)	−0.0195 (15)	0.0038 (12)	−0.0426 (16)
O3	0.0404 (13)	0.0218 (12)	0.0256 (12)	−0.0050 (10)	0.0105 (9)	−0.0046 (10)
O4	0.0418 (13)	0.0206 (11)	0.0252 (12)	−0.0018 (9)	0.0097 (9)	−0.0094 (10)
O5	0.0482 (14)	0.0345 (14)	0.0537 (16)	−0.0119 (11)	0.0227 (12)	−0.0238 (13)
O6	0.0566 (15)	0.0294 (13)	0.0500 (16)	0.0142 (11)	−0.0223 (12)	−0.0233 (12)
O7	0.0427 (15)	0.070 (2)	0.0324 (14)	0.0181 (13)	0.0001 (11)	−0.0017 (14)
O8	0.084 (2)	0.0508 (18)	0.0592 (18)	−0.0392 (16)	0.0194 (15)	−0.0209 (15)
O9	0.0598 (16)	0.0507 (16)	0.0282 (13)	−0.0267 (13)	0.0082 (11)	−0.0153 (12)
O10	0.0355 (13)	0.0561 (16)	0.0248 (12)	0.0080 (11)	0.0014 (10)	−0.0112 (12)
O11	0.0440 (13)	0.0326 (13)	0.0296 (12)	−0.0136 (10)	0.0122 (10)	−0.0177 (11)
O12	0.0340 (13)	0.0321 (14)	0.0493 (15)	0.0073 (11)	0.0030 (11)	−0.0073 (12)
O13	0.0350 (13)	0.0252 (12)	0.0366 (14)	0.0011 (10)	0.0130 (10)	−0.0012 (11)
O14	0.0351 (13)	0.0657 (18)	0.0311 (13)	0.0066 (12)	−0.0051 (11)	−0.0197 (13)
O15	0.0321 (12)	0.0439 (14)	0.0251 (12)	0.0044 (10)	0.0029 (9)	−0.0157 (11)
O16	0.0419 (13)	0.0200 (11)	0.0293 (12)	−0.0041 (9)	0.0051 (10)	−0.0106 (10)
O17	0.0422 (13)	0.0266 (12)	0.0212 (11)	0.0029 (10)	0.0025 (9)	−0.0078 (10)
O18	0.0511 (14)	0.0304 (13)	0.0265 (13)	0.0092 (11)	−0.0111 (11)	−0.0086 (11)
O19	0.0591 (16)	0.0336 (14)	0.0386 (14)	0.0016 (12)	−0.0150 (11)	−0.0189 (12)
C1	0.0198 (14)	0.0247 (17)	0.0205 (15)	−0.0017 (12)	0.0012 (11)	−0.0055 (14)
C2	0.0263 (15)	0.0168 (15)	0.0199 (15)	−0.0026 (12)	0.0026 (12)	−0.0057 (13)
C3	0.0294 (16)	0.0213 (16)	0.0251 (16)	−0.0014 (13)	0.0001 (13)	−0.0059 (13)
C4	0.0423 (19)	0.0258 (17)	0.0178 (16)	0.0012 (14)	−0.0033 (13)	−0.0042 (14)
C5	0.046 (2)	0.0273 (17)	0.0192 (16)	−0.0031 (15)	0.0066 (14)	−0.0092 (14)
C6	0.0281 (16)	0.0218 (16)	0.0266 (16)	0.0003 (13)	0.0050 (13)	−0.0107 (14)
C7	0.0278 (15)	0.0168 (15)	0.0219 (15)	−0.0008 (12)	−0.0001 (12)	−0.0073 (13)
C8	0.0254 (16)	0.047 (2)	0.0248 (17)	0.0058 (15)	0.0048 (13)	−0.0177 (17)
C9	0.0279 (16)	0.0206 (15)	0.0229 (16)	−0.0006 (13)	−0.0013 (13)	−0.0076 (13)
C10	0.0170 (14)	0.0267 (16)	0.0237 (16)	−0.0022 (12)	0.0016 (11)	−0.0078 (14)
C11	0.0200 (15)	0.0255 (17)	0.0312 (17)	−0.0025 (12)	−0.0005 (12)	−0.0089 (14)
C12	0.0186 (14)	0.0294 (17)	0.0251 (16)	−0.0051 (13)	−0.0021 (12)	0.0004 (14)
C13	0.0192 (15)	0.0395 (19)	0.0220 (16)	−0.0048 (13)	−0.0006 (12)	−0.0102 (15)
C14	0.0204 (15)	0.0315 (18)	0.0303 (17)	−0.0053 (13)	0.0031 (12)	−0.0156 (15)
C15	0.0171 (14)	0.0258 (16)	0.0241 (16)	−0.0027 (12)	0.0003 (11)	−0.0079 (13)
C16	0.0245 (16)	0.0265 (17)	0.0254 (16)	−0.0025 (13)	0.0002 (12)	−0.0115 (14)
C17	0.0275 (16)	0.0238 (17)	0.0290 (17)	−0.0047 (13)	0.0005 (13)	−0.0078 (14)
C18	0.0319 (16)	0.0174 (15)	0.0202 (15)	0.0008 (13)	−0.0003 (12)	−0.0068 (13)
C19	0.0365 (18)	0.0218 (16)	0.0288 (17)	−0.0031 (14)	0.0030 (13)	−0.0100 (14)
C20	0.048 (2)	0.0203 (16)	0.0211 (16)	0.0017 (14)	0.0082 (14)	−0.0051 (14)
C21	0.0416 (19)	0.0280 (17)	0.0199 (16)	0.0090 (14)	−0.0036 (13)	−0.0093 (14)
C22	0.0335 (17)	0.0266 (17)	0.0257 (17)	0.0013 (13)	−0.0018 (13)	−0.0134 (14)
C23	0.0295 (16)	0.0204 (15)	0.0199 (15)	0.0013 (12)	0.0008 (12)	−0.0090 (13)
C24	0.0234 (15)	0.0239 (16)	0.0242 (16)	−0.0015 (12)	−0.0038 (12)	−0.0074 (14)
O20	0.0344 (14)	0.0505 (17)	0.0646 (18)	−0.0028 (12)	0.0126 (12)	−0.0052 (14)

Geometric parameters (Å, º)

Pr1—O1	2.424 (2)	O12—C16	1.197 (4)
Pr1—O11	2.432 (2)	O13—C16	1.315 (3)
Pr1—O10	2.451 (2)	O13—H13	0.8200
Pr1—O8	2.466 (3)	O14—C9	1.211 (4)
Pr1—O6	2.486 (2)	O15—C9	1.297 (4)
Pr1—O5	2.491 (2)	O15—H15	0.8200
Pr1—O9	2.505 (2)	O16—C24	1.254 (4)
Pr1—O7	2.507 (2)	O17—C24	1.249 (3)
Cl1—C3	1.724 (3)	O18—C17	1.299 (4)
Cl2—C4	1.714 (3)	O18—H18	0.8200
Cl3—C5	1.716 (3)	O19—C17	1.209 (4)
Cl4—C6	1.717 (3)	C1—C2	1.517 (4)
Cl5—C11	1.722 (3)	C2—C3	1.381 (4)
Cl6—C12	1.716 (3)	C2—C7	1.390 (4)
Cl7—C13	1.718 (3)	C3—C4	1.393 (4)
Cl8—C14	1.713 (3)	C4—C5	1.388 (4)
Cl9—C19	1.721 (3)	C5—C6	1.392 (4)
Cl10—C20	1.710 (3)	C6—C7	1.389 (4)
Cl11—C21	1.711 (3)	C7—C8	1.505 (4)
Cl12—C22	1.730 (3)	C9—C10	1.504 (4)
O1—C8	1.248 (4)	C10—C11	1.389 (4)
O2—C8	1.242 (4)	C10—C15	1.397 (4)
O3—C1	1.250 (3)	C11—C12	1.392 (4)
O4—C1	1.248 (3)	C12—C13	1.387 (4)
O5—H5A	0.8499	C13—C14	1.394 (4)
O5—H5B	0.8500	C14—C15	1.394 (4)
O6—H6A	0.8543	C15—C16	1.493 (4)
O6—H6B	0.8971	C17—C18	1.507 (4)
O7—H7A	0.8496	C18—C19	1.383 (4)
O7—H7B	0.8496	C18—C23	1.395 (4)
O8—H8A	0.8501	C19—C20	1.396 (4)
O8—H8B	0.8497	C20—C21	1.389 (5)
O9—H9A	0.8499	C21—C22	1.389 (4)
O9—H9B	0.8498	C22—C23	1.383 (4)
O10—H10A	0.8499	C23—C24	1.510 (4)
O10—H10B	0.8501	O20—H20A	0.8500
O11—H11A	0.8502	O20—H20B	0.8500
O11—H11B	0.8501
O1—Pr1—O11	103.91 (9)	C5—C4—Cl2	120.2 (2)
O1—Pr1—O10	71.43 (8)	C3—C4—Cl2	120.2 (2)
O11—Pr1—O10	95.27 (8)	C4—C5—C6	119.9 (3)
O1—Pr1—O8	111.43 (10)	C4—C5—Cl3	119.9 (2)
O11—Pr1—O8	137.39 (8)	C6—C5—Cl3	120.1 (2)
O10—Pr1—O8	74.98 (9)	C7—C6—C5	120.4 (3)
O1—Pr1—O6	66.99 (8)	C7—C6—Cl4	119.4 (2)
O11—Pr1—O6	146.98 (8)	C5—C6—Cl4	120.2 (2)
O10—Pr1—O6	110.23 (8)	C6—C7—C2	119.3 (3)
O8—Pr1—O6	71.71 (9)	C6—C7—C8	121.6 (3)
O1—Pr1—O5	78.11 (9)	C2—C7—C8	119.1 (2)
O11—Pr1—O5	71.22 (7)	O2—C8—O1	124.2 (3)
O10—Pr1—O5	142.56 (8)	O2—C8—C7	118.5 (3)
O8—Pr1—O5	138.10 (9)	O1—C8—C7	117.3 (3)
O6—Pr1—O5	75.81 (8)	O14—C9—O15	125.3 (3)
O1—Pr1—O9	141.85 (8)	O14—C9—C10	120.6 (3)
O11—Pr1—O9	67.39 (7)	O15—C9—C10	114.1 (2)
O10—Pr1—O9	72.55 (8)	C11—C10—C15	120.1 (3)
O8—Pr1—O9	70.14 (8)	C11—C10—C9	121.1 (3)
O6—Pr1—O9	139.36 (8)	C15—C10—C9	118.8 (3)
O5—Pr1—O9	127.66 (8)	C10—C11—C12	120.4 (3)
O1—Pr1—O7	139.14 (8)	C10—C11—Cl5	119.4 (2)
O11—Pr1—O7	94.67 (9)	C12—C11—Cl5	120.2 (2)
O10—Pr1—O7	143.21 (8)	C13—C12—C11	119.7 (3)
O8—Pr1—O7	73.80 (10)	C13—C12—Cl6	120.2 (2)
O6—Pr1—O7	77.57 (8)	C11—C12—Cl6	120.1 (2)
O5—Pr1—O7	73.94 (8)	C12—C13—C14	120.1 (3)
O9—Pr1—O7	78.90 (9)	C12—C13—Cl7	120.2 (2)
C8—O1—Pr1	117.0 (2)	C14—C13—Cl7	119.7 (2)
Pr1—O5—H5A	123.5	C13—C14—C15	120.3 (3)
Pr1—O5—H5B	113.4	C13—C14—Cl8	119.6 (2)
H5A—O5—H5B	116.8	C15—C14—Cl8	120.0 (2)
Pr1—O6—H6A	131.8	C14—C15—C10	119.4 (3)
Pr1—O6—H6B	112.5	C14—C15—C16	120.7 (3)
H6A—O6—H6B	115.7	C10—C15—C16	120.0 (3)
Pr1—O7—H7A	120.5	O12—C16—O13	124.7 (3)
Pr1—O7—H7B	122.4	O12—C16—C15	123.4 (3)
H7A—O7—H7B	117.0	O13—C16—C15	111.8 (3)
Pr1—O8—H8A	123.8	O19—C17—O18	124.9 (3)
Pr1—O8—H8B	119.8	O19—C17—C18	122.5 (3)
H8A—O8—H8B	116.4	O18—C17—C18	112.6 (3)
Pr1—O9—H9A	120.2	C19—C18—C23	119.8 (3)
Pr1—O9—H9B	122.5	C19—C18—C17	121.1 (3)
H9A—O9—H9B	116.2	C23—C18—C17	119.0 (3)
Pr1—O10—H10A	117.8	C18—C19—C20	120.6 (3)
Pr1—O10—H10B	124.9	C18—C19—Cl9	119.9 (2)
H10A—O10—H10B	116.1	C20—C19—Cl9	119.5 (2)
Pr1—O11—H11A	120.1	C21—C20—C19	119.5 (3)
Pr1—O11—H11B	121.0	C21—C20—Cl10	120.3 (3)
H11A—O11—H11B	115.4	C19—C20—Cl10	120.1 (3)
C16—O13—H13	109.5	C20—C21—C22	119.5 (3)
C9—O15—H15	109.5	C20—C21—Cl11	120.2 (2)
C17—O18—H18	109.5	C22—C21—Cl11	120.3 (3)
O4—C1—O3	124.6 (3)	C23—C22—C21	121.1 (3)
O4—C1—C2	118.8 (3)	C23—C22—Cl12	118.7 (2)
O3—C1—C2	116.5 (3)	C21—C22—Cl12	120.3 (2)
C3—C2—C7	120.5 (3)	C22—C23—C18	119.4 (3)
C3—C2—C1	121.1 (3)	C22—C23—C24	121.4 (3)
C7—C2—C1	118.3 (2)	C18—C23—C24	119.2 (2)
C2—C3—C4	120.1 (3)	O17—C24—O16	125.8 (3)
C2—C3—Cl1	120.1 (2)	O17—C24—C23	117.0 (3)
C4—C3—Cl1	119.7 (2)	O16—C24—C23	117.2 (3)
C5—C4—C3	119.6 (3)	H20A—O20—H20B	116.1
O11—Pr1—O1—C8	−17.7 (3)	C11—C12—C13—C14	−0.8 (4)
O10—Pr1—O1—C8	73.2 (2)	Cl6—C12—C13—C14	178.7 (2)
O8—Pr1—O1—C8	138.0 (2)	C11—C12—C13—Cl7	179.0 (2)
O6—Pr1—O1—C8	−164.2 (3)	Cl6—C12—C13—Cl7	−1.5 (4)
O5—Pr1—O1—C8	−84.7 (2)	C12—C13—C14—C15	0.7 (4)
O9—Pr1—O1—C8	53.2 (3)	Cl7—C13—C14—C15	−179.0 (2)
O7—Pr1—O1—C8	−132.2 (2)	C12—C13—C14—Cl8	178.1 (2)
O4—C1—C2—C3	−69.0 (4)	Cl7—C13—C14—Cl8	−1.6 (3)
O3—C1—C2—C3	112.9 (3)	C13—C14—C15—C10	0.3 (4)
O4—C1—C2—C7	113.5 (3)	Cl8—C14—C15—C10	−177.1 (2)
O3—C1—C2—C7	−64.5 (3)	C13—C14—C15—C16	180.0 (3)
C7—C2—C3—C4	−1.2 (4)	Cl8—C14—C15—C16	2.6 (4)
C1—C2—C3—C4	−178.6 (3)	C11—C10—C15—C14	−1.2 (4)
C7—C2—C3—Cl1	177.4 (2)	C9—C10—C15—C14	−178.4 (3)
C1—C2—C3—Cl1	0.0 (4)	C11—C10—C15—C16	179.1 (3)
C2—C3—C4—C5	−1.5 (5)	C9—C10—C15—C16	1.9 (4)
Cl1—C3—C4—C5	179.8 (2)	C14—C15—C16—O12	54.6 (4)
C2—C3—C4—Cl2	178.0 (2)	C10—C15—C16—O12	−125.7 (3)
Cl1—C3—C4—Cl2	−0.7 (4)	C14—C15—C16—O13	−125.9 (3)
C3—C4—C5—C6	2.5 (5)	C10—C15—C16—O13	53.8 (4)
Cl2—C4—C5—C6	−177.0 (2)	O19—C17—C18—C19	−59.9 (4)
C3—C4—C5—Cl3	−178.1 (2)	O18—C17—C18—C19	121.4 (3)
Cl2—C4—C5—Cl3	2.4 (4)	O19—C17—C18—C23	117.6 (3)
C4—C5—C6—C7	−0.7 (5)	O18—C17—C18—C23	−61.1 (4)
Cl3—C5—C6—C7	179.9 (2)	C23—C18—C19—C20	−0.8 (4)
C4—C5—C6—Cl4	179.1 (2)	C17—C18—C19—C20	176.8 (3)
Cl3—C5—C6—Cl4	−0.3 (4)	C23—C18—C19—Cl9	178.5 (2)
C5—C6—C7—C2	−2.0 (4)	C17—C18—C19—Cl9	−3.9 (4)
Cl4—C6—C7—C2	178.2 (2)	C18—C19—C20—C21	−2.5 (5)
C5—C6—C7—C8	176.4 (3)	Cl9—C19—C20—C21	178.2 (2)
Cl4—C6—C7—C8	−3.4 (4)	C18—C19—C20—Cl10	176.7 (2)
C3—C2—C7—C6	3.0 (4)	Cl9—C19—C20—Cl10	−2.6 (4)
C1—C2—C7—C6	−179.6 (3)	C19—C20—C21—C22	3.4 (4)
C3—C2—C7—C8	−175.5 (3)	Cl10—C20—C21—C22	−175.8 (2)
C1—C2—C7—C8	2.0 (4)	C19—C20—C21—Cl11	−177.3 (2)
Pr1—O1—C8—O2	0.9 (4)	Cl10—C20—C21—Cl11	3.6 (4)
Pr1—O1—C8—C7	−177.05 (19)	C20—C21—C22—C23	−1.1 (4)
C6—C7—C8—O2	114.8 (3)	Cl11—C21—C22—C23	179.5 (2)
C2—C7—C8—O2	−66.8 (4)	C20—C21—C22—Cl12	−179.7 (2)
C6—C7—C8—O1	−67.1 (4)	Cl11—C21—C22—Cl12	0.9 (4)
C2—C7—C8—O1	111.3 (3)	C21—C22—C23—C18	−2.1 (4)
O14—C9—C10—C11	−105.4 (3)	Cl12—C22—C23—C18	176.5 (2)
O15—C9—C10—C11	75.3 (3)	C21—C22—C23—C24	177.6 (3)
O14—C9—C10—C15	71.8 (4)	Cl12—C22—C23—C24	−3.7 (4)
O15—C9—C10—C15	−107.5 (3)	C19—C18—C23—C22	3.1 (4)
C15—C10—C11—C12	1.2 (4)	C17—C18—C23—C22	−174.5 (3)
C9—C10—C11—C12	178.3 (3)	C19—C18—C23—C24	−176.7 (3)
C15—C10—C11—Cl5	−177.7 (2)	C17—C18—C23—C24	5.7 (4)
C9—C10—C11—Cl5	−0.6 (4)	C22—C23—C24—O17	107.5 (3)
C10—C11—C12—C13	−0.2 (4)	C18—C23—C24—O17	−72.8 (4)
Cl5—C11—C12—C13	178.7 (2)	C22—C23—C24—O16	−72.9 (4)
C10—C11—C12—Cl6	−179.7 (2)	C18—C23—C24—O16	106.9 (3)
Cl5—C11—C12—Cl6	−0.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O3^i	0.85	1.92	2.727 (4)	158
O5—H5B···O19^ii	0.85	1.95	2.791 (4)	172
O6—H6A···O17^ii	0.85	1.89	2.732 (4)	170
O7—H7A···O19^ii	0.85	2.25	3.034 (4)	153
O7—H7B···O14^iii	0.85	2.05	2.897 (3)	172
O8—H8A···O20^iv	0.85	1.88	2.715 (4)	167
O8—H8B···O16^iv	0.85	2.15	2.760 (4)	129
O9—H9A···O20^iv	0.85	1.95	2.787 (4)	166
O9—H9B···O2^v	0.85	2.10	2.916 (4)	161
O10—H10A···O4^vi	0.85	1.90	2.736 (3)	168
O10—H10B···O3	0.85	2.03	2.858 (3)	164
O11—H11A···O2^v	0.85	1.87	2.716 (4)	174
O11—H11B···O3^i	0.85	1.89	2.692 (3)	158
O13—H13···O4^vii	0.82	1.75	2.558 (3)	167
O15—H15···O16^viii	0.82	1.78	2.590 (3)	168
O18—H18···O17^ix	0.82	1.78	2.580 (3)	166
O20—H20A···O14^ii	0.85	2.05	2.817 (4)	149
O20—H20B···O13^viii	0.85	2.18	2.850 (4)	135
O20—H20B···O15^viii	0.85	2.59	3.171 (4)	127

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