Di­aqua­tris­(nicotinato-κO)­bis(1,10-phenanthroline-κ²N,N′)­praseodymium(III) trihydrate

The structure of the title compound, [Pr(C₆H₄NO₂)₃(C₁₂H₈N₂)₂(H₂O)₂]·3H₂O, is composed of a discrete neutral Pr complex and solvent water mol­ecules. The Pr^III center is nine-coordinate and exhibits a monocapped square-antiprismatic coordination geometry formed by three O atoms of distinct nicotinate groups, four N-atom donors of two 1,10-phenanthroline mol­ecules and two aqua ligands.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.032
• wR factor = 0.065
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.99
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.63 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Pr1    -   O8      ..       5.77 su
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          6
PLAT731_ALERT_1_C Bond    Calc     0.83(4), Rep   0.831(19) ......       2.11 su-Rat
              O8   -H8A     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.81(4), Rep   0.816(18) ......       2.22 su-Rat
              O3W  -H3WA    1.555   1.555

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 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
   2 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); 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.

Diaquatris(nicotinato-κO)bis(1,10-phenanthroline-κ²N,N')praseodymium(III) trihydrate

Crystal data

[Pr(C6H4NO2)3(C12H8N2)2(H2O)2]·3H2O	Z = 2
Mr = 957.70	F(000) = 972
Triclinic, P1	Dx = 1.557 Mg m^−3
Hall symbol: -P 1	Melting point: not measured K
a = 9.058 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.922 (5) Å	Cell parameters from 885 reflections
c = 17.826 (6) Å	θ = 2.9–26.3°
α = 84.966 (5)°	µ = 1.26 mm^−1
β = 80.597 (5)°	T = 293 K
γ = 84.398 (5)°	Prism, colorless
V = 2043.1 (12) Å^3	0.24 × 0.24 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer	8275 independent reflections
Radiation source: fine-focus sealed tube	7083 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 0 pixels mm^-1	θmax = 26.4°, θmin = 2.0°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996; Blessing, 1995)	k = −16→12
Tmin = 0.751, Tmax = 0.769	l = −17→22
11836 measured reflections

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.065	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0268P)^2] where P = (Fo^2 + 2Fc^2)/3
8275 reflections	(Δ/σ)max = 0.003
590 parameters	Δρmax = 0.32 e Å^−3
11 restraints	Δρmin = −0.42 e Å^−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	0.585016 (17)	0.741776 (12)	0.736335 (8)	0.02610 (5)
N1	0.7053 (4)	0.2525 (2)	0.74781 (18)	0.0622 (8)
N2	0.9309 (4)	0.6561 (3)	0.39066 (16)	0.0766 (11)
N3	0.9577 (4)	0.7757 (3)	1.00074 (19)	0.0809 (11)
N4	0.7489 (3)	0.59784 (18)	0.81641 (13)	0.0354 (6)
N5	0.4956 (3)	0.70233 (19)	0.88708 (13)	0.0370 (6)
N6	0.6894 (3)	0.90469 (17)	0.64088 (13)	0.0335 (5)
N7	0.5065 (3)	0.77360 (19)	0.59616 (13)	0.0384 (6)
C1	0.4487 (3)	0.4978 (2)	0.72692 (16)	0.0373 (7)
C2	0.5028 (4)	0.3842 (2)	0.73885 (16)	0.0377 (7)
C3	0.4002 (4)	0.3108 (3)	0.76359 (18)	0.0513 (9)
H3A	0.2976	0.3300	0.7688	0.062*
C4	0.4523 (5)	0.2091 (3)	0.7803 (2)	0.0683 (12)
H4A	0.3857	0.1583	0.7966	0.082*
C5	0.6028 (6)	0.1845 (3)	0.7726 (2)	0.0712 (12)
H5A	0.6369	0.1160	0.7854	0.085*
C6	0.6517 (4)	0.3512 (2)	0.73088 (18)	0.0468 (8)
H6A	0.7206	0.3999	0.7126	0.056*
C7	0.9077 (3)	0.7076 (2)	0.59628 (16)	0.0364 (7)
C8	0.8813 (3)	0.6593 (2)	0.52674 (16)	0.0374 (7)
C9	0.9531 (4)	0.6910 (3)	0.45559 (18)	0.0577 (10)
H9A	1.0221	0.7405	0.4527	0.069*
C10	0.8347 (5)	0.5840 (3)	0.3963 (2)	0.0746 (12)
H10A	0.8209	0.5559	0.3519	0.089*
C11	0.7541 (5)	0.5485 (3)	0.4639 (2)	0.0720 (12)
H11A	0.6848	0.4997	0.4649	0.086*
C12	0.7778 (4)	0.5865 (3)	0.53043 (19)	0.0546 (9)
H12A	0.7250	0.5635	0.5771	0.065*
C13	0.6952 (3)	0.8909 (2)	0.86584 (16)	0.0356 (7)
C14	0.7768 (3)	0.8759 (2)	0.93345 (16)	0.0377 (7)
C15	0.7392 (4)	0.9408 (3)	0.99188 (19)	0.0569 (9)
H15A	0.6646	0.9953	0.9895	0.068*
C16	0.8135 (5)	0.9241 (4)	1.0541 (2)	0.0777 (13)
H16A	0.7919	0.9679	1.0939	0.093*
C17	0.9191 (5)	0.8418 (4)	1.0558 (2)	0.0873 (15)
H17A	0.9678	0.8307	1.0982	0.105*
C18	0.8865 (4)	0.7947 (3)	0.94056 (19)	0.0553 (9)
H18A	0.9120	0.7508	0.9010	0.066*
C19	0.8681 (4)	0.5423 (3)	0.78323 (19)	0.0496 (8)
H19A	0.8942	0.5528	0.7306	0.060*
C20	0.9576 (4)	0.4688 (3)	0.8220 (2)	0.0600 (10)
H20A	1.0396	0.4313	0.7955	0.072*
C21	0.9230 (4)	0.4528 (3)	0.8987 (2)	0.0579 (10)
H21A	0.9801	0.4034	0.9254	0.070*
C22	0.8001 (4)	0.5117 (3)	0.93739 (18)	0.0451 (8)
C23	0.7606 (5)	0.5018 (3)	1.0183 (2)	0.0594 (10)
H23A	0.8168	0.4545	1.0470	0.071*
C24	0.6442 (5)	0.5595 (3)	1.05295 (19)	0.0611 (10)
H24A	0.6230	0.5538	1.1059	0.073*
C25	0.5506 (4)	0.6302 (3)	1.01122 (18)	0.0483 (8)
C26	0.4252 (5)	0.6895 (3)	1.0451 (2)	0.0627 (10)
H26A	0.4013	0.6863	1.0980	0.075*
C27	0.3376 (4)	0.7518 (3)	1.0025 (2)	0.0610 (10)
H27A	0.2541	0.7917	1.0253	0.073*
C28	0.3755 (4)	0.7549 (3)	0.92248 (19)	0.0500 (8)
H28A	0.3131	0.7960	0.8931	0.060*
C29	0.5832 (3)	0.6408 (2)	0.93100 (16)	0.0371 (7)
C30	0.7136 (3)	0.5822 (2)	0.89337 (15)	0.0351 (7)
C31	0.7717 (3)	0.9725 (2)	0.66200 (17)	0.0406 (7)
H31A	0.7802	0.9709	0.7134	0.049*
C32	0.8468 (4)	1.0465 (2)	0.61192 (18)	0.0457 (8)
H32A	0.9027	1.0930	0.6298	0.055*
C33	0.8364 (4)	1.0492 (2)	0.53662 (19)	0.0465 (8)
H33A	0.8865	1.0973	0.5022	0.056*
C34	0.7501 (3)	0.9794 (2)	0.51102 (16)	0.0375 (7)
C35	0.7334 (4)	0.9791 (3)	0.43327 (17)	0.0485 (8)
H35A	0.7838	1.0251	0.3972	0.058*
C36	0.6461 (4)	0.9136 (3)	0.41111 (18)	0.0513 (9)
H36A	0.6378	0.9145	0.3597	0.062*
C37	0.5658 (3)	0.8427 (2)	0.46414 (17)	0.0418 (7)
C38	0.4673 (4)	0.7774 (3)	0.44435 (19)	0.0525 (9)
H38A	0.4563	0.7759	0.3935	0.063*
C39	0.3868 (4)	0.7158 (3)	0.4989 (2)	0.0572 (9)
H39A	0.3170	0.6749	0.4861	0.069*
C40	0.4112 (4)	0.7152 (3)	0.57423 (18)	0.0484 (8)
H40A	0.3577	0.6716	0.6109	0.058*
C41	0.5814 (3)	0.8385 (2)	0.54203 (16)	0.0346 (7)
C42	0.6765 (3)	0.9082 (2)	0.56559 (16)	0.0335 (6)
O1	0.3115 (3)	0.52023 (18)	0.73600 (16)	0.0622 (7)
O2	0.5474 (2)	0.56218 (15)	0.71000 (11)	0.0391 (5)
O3	0.8113 (2)	0.69427 (15)	0.65577 (10)	0.0374 (5)
O4	1.0197 (2)	0.75666 (19)	0.59222 (12)	0.0543 (6)
O5	0.7346 (2)	0.82948 (15)	0.81289 (10)	0.0358 (5)
O6	0.5922 (3)	0.96169 (17)	0.86650 (13)	0.0565 (6)
O7	0.3116 (3)	0.71899 (19)	0.75653 (14)	0.0466 (5)
O8	0.4363 (3)	0.90791 (18)	0.76753 (14)	0.0460 (5)
O1W	−0.0213 (4)	0.8011 (2)	0.25713 (19)	0.0736 (8)
O2W	0.9608 (3)	0.1793 (2)	0.26813 (16)	0.0524 (6)
O3W	0.8471 (3)	0.0011 (2)	0.23119 (17)	0.0636 (7)
H7A	0.294 (4)	0.6576 (16)	0.7533 (19)	0.052 (11)*
H7B	0.231 (3)	0.751 (3)	0.751 (2)	0.077 (14)*
H8A	0.476 (4)	0.937 (3)	0.7979 (19)	0.086 (15)*
H8B	0.354 (3)	0.942 (3)	0.767 (2)	0.087 (15)*
H1WA	0.071 (2)	0.786 (4)	0.247 (2)	0.11 (2)*
H1WB	−0.049 (5)	0.766 (3)	0.2961 (19)	0.12 (2)*
H2WA	0.960 (4)	0.194 (3)	0.3125 (12)	0.067 (13)*
H2WB	1.045 (3)	0.185 (3)	0.2446 (17)	0.055 (11)*
H3WA	0.895 (4)	0.045 (3)	0.243 (2)	0.076 (14)*
H3WB	0.885 (4)	−0.0577 (18)	0.238 (2)	0.082 (15)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pr1	0.02732 (8)	0.02448 (8)	0.02624 (8)	−0.00142 (5)	−0.00521 (6)	0.00062 (6)
N1	0.072 (2)	0.0397 (17)	0.069 (2)	0.0113 (15)	−0.0030 (16)	−0.0036 (16)
N2	0.100 (3)	0.098 (3)	0.0361 (17)	−0.035 (2)	−0.0051 (17)	−0.0074 (18)
N3	0.087 (3)	0.098 (3)	0.061 (2)	0.021 (2)	−0.0408 (19)	−0.004 (2)
N4	0.0397 (14)	0.0338 (13)	0.0309 (13)	0.0018 (11)	−0.0052 (11)	0.0015 (11)
N5	0.0369 (14)	0.0367 (14)	0.0346 (13)	−0.0044 (11)	0.0027 (11)	−0.0005 (11)
N6	0.0395 (14)	0.0274 (13)	0.0328 (13)	0.0007 (10)	−0.0072 (11)	0.0009 (10)
N7	0.0422 (15)	0.0369 (14)	0.0384 (14)	−0.0073 (12)	−0.0145 (11)	0.0041 (12)
C1	0.0431 (18)	0.0347 (16)	0.0352 (16)	−0.0063 (14)	−0.0064 (13)	−0.0042 (13)
C2	0.0501 (19)	0.0305 (16)	0.0319 (15)	−0.0088 (14)	−0.0004 (13)	−0.0033 (13)
C3	0.058 (2)	0.0392 (19)	0.054 (2)	−0.0120 (16)	0.0052 (17)	−0.0059 (16)
C4	0.095 (3)	0.037 (2)	0.067 (3)	−0.019 (2)	0.016 (2)	−0.0055 (19)
C5	0.110 (4)	0.0291 (19)	0.066 (3)	0.004 (2)	0.004 (2)	0.0000 (18)
C6	0.054 (2)	0.0347 (17)	0.0486 (19)	−0.0034 (15)	0.0003 (16)	0.0003 (15)
C7	0.0374 (17)	0.0356 (16)	0.0341 (16)	−0.0023 (13)	−0.0030 (13)	0.0037 (13)
C8	0.0406 (17)	0.0346 (16)	0.0348 (16)	−0.0004 (13)	−0.0018 (13)	−0.0010 (13)
C9	0.065 (2)	0.071 (3)	0.0386 (19)	−0.030 (2)	−0.0010 (17)	0.0007 (18)
C10	0.104 (4)	0.077 (3)	0.050 (2)	−0.020 (3)	−0.019 (2)	−0.016 (2)
C11	0.101 (3)	0.059 (3)	0.064 (3)	−0.037 (2)	−0.012 (2)	−0.012 (2)
C12	0.071 (2)	0.047 (2)	0.0451 (19)	−0.0199 (18)	0.0001 (17)	−0.0002 (17)
C13	0.0442 (18)	0.0282 (15)	0.0365 (16)	−0.0084 (13)	−0.0106 (13)	−0.0001 (13)
C14	0.0411 (17)	0.0388 (17)	0.0338 (16)	−0.0043 (14)	−0.0085 (13)	0.0001 (14)
C15	0.063 (2)	0.062 (2)	0.047 (2)	0.0037 (18)	−0.0146 (17)	−0.0163 (18)
C16	0.087 (3)	0.109 (4)	0.042 (2)	0.000 (3)	−0.022 (2)	−0.024 (2)
C17	0.089 (3)	0.135 (5)	0.044 (2)	0.004 (3)	−0.035 (2)	−0.004 (3)
C18	0.062 (2)	0.061 (2)	0.046 (2)	0.0062 (18)	−0.0222 (17)	−0.0063 (18)
C19	0.050 (2)	0.050 (2)	0.0430 (18)	0.0102 (16)	−0.0028 (15)	0.0047 (16)
C20	0.052 (2)	0.058 (2)	0.063 (2)	0.0210 (18)	−0.0073 (18)	0.0100 (19)
C21	0.053 (2)	0.050 (2)	0.071 (3)	0.0032 (17)	−0.0266 (19)	0.0150 (19)
C22	0.052 (2)	0.0453 (19)	0.0424 (18)	−0.0140 (16)	−0.0229 (15)	0.0120 (15)
C23	0.075 (3)	0.063 (2)	0.045 (2)	−0.016 (2)	−0.0298 (19)	0.0141 (19)
C24	0.090 (3)	0.071 (3)	0.0272 (17)	−0.022 (2)	−0.0235 (19)	0.0105 (18)
C25	0.058 (2)	0.053 (2)	0.0351 (17)	−0.0189 (17)	−0.0026 (16)	−0.0038 (16)
C26	0.082 (3)	0.073 (3)	0.0316 (18)	−0.018 (2)	0.0044 (19)	−0.0075 (19)
C27	0.060 (2)	0.068 (3)	0.050 (2)	−0.011 (2)	0.0168 (18)	−0.017 (2)
C28	0.046 (2)	0.048 (2)	0.050 (2)	−0.0021 (16)	0.0066 (16)	−0.0016 (17)
C29	0.0453 (18)	0.0391 (17)	0.0282 (15)	−0.0131 (14)	−0.0061 (13)	0.0009 (13)
C30	0.0430 (17)	0.0325 (16)	0.0313 (15)	−0.0097 (13)	−0.0094 (13)	0.0025 (13)
C31	0.0488 (19)	0.0360 (17)	0.0372 (17)	−0.0061 (14)	−0.0075 (14)	0.0008 (14)
C32	0.056 (2)	0.0335 (17)	0.0485 (19)	−0.0123 (15)	−0.0065 (16)	0.0000 (15)
C33	0.050 (2)	0.0353 (18)	0.049 (2)	−0.0032 (15)	0.0031 (15)	0.0065 (15)
C34	0.0403 (17)	0.0324 (16)	0.0360 (16)	0.0018 (13)	−0.0007 (13)	0.0043 (13)
C35	0.057 (2)	0.050 (2)	0.0330 (17)	−0.0026 (17)	0.0003 (15)	0.0089 (15)
C36	0.062 (2)	0.060 (2)	0.0294 (16)	0.0030 (18)	−0.0083 (15)	0.0038 (16)
C37	0.0445 (18)	0.0464 (19)	0.0349 (16)	0.0042 (15)	−0.0128 (14)	−0.0020 (15)
C38	0.063 (2)	0.058 (2)	0.0404 (19)	0.0030 (18)	−0.0228 (17)	−0.0031 (17)
C39	0.066 (2)	0.055 (2)	0.059 (2)	−0.0137 (19)	−0.0322 (19)	−0.0006 (19)
C40	0.057 (2)	0.047 (2)	0.0460 (19)	−0.0136 (16)	−0.0202 (16)	0.0065 (16)
C41	0.0379 (16)	0.0307 (16)	0.0333 (16)	0.0046 (13)	−0.0067 (13)	0.0012 (13)
C42	0.0363 (16)	0.0282 (15)	0.0328 (15)	0.0049 (12)	−0.0045 (12)	0.0048 (12)
O1	0.0366 (13)	0.0408 (13)	0.109 (2)	−0.0046 (10)	−0.0096 (13)	−0.0067 (14)
O2	0.0373 (11)	0.0303 (11)	0.0492 (12)	−0.0072 (9)	−0.0041 (9)	−0.0002 (9)
O3	0.0390 (11)	0.0369 (11)	0.0323 (11)	−0.0027 (9)	0.0035 (9)	0.0023 (9)
O4	0.0470 (14)	0.0740 (17)	0.0432 (13)	−0.0252 (13)	0.0015 (10)	−0.0064 (12)
O5	0.0396 (11)	0.0356 (11)	0.0334 (11)	−0.0030 (9)	−0.0088 (9)	−0.0041 (9)
O6	0.0727 (17)	0.0406 (13)	0.0616 (15)	0.0169 (12)	−0.0336 (13)	−0.0147 (12)
O7	0.0344 (13)	0.0378 (14)	0.0694 (16)	−0.0025 (11)	−0.0123 (11)	−0.0078 (12)
O8	0.0425 (14)	0.0396 (13)	0.0583 (15)	0.0051 (11)	−0.0164 (11)	−0.0111 (11)
O1W	0.076 (2)	0.070 (2)	0.068 (2)	0.0130 (17)	−0.0098 (16)	0.0079 (17)
O2W	0.0380 (14)	0.0622 (16)	0.0612 (17)	−0.0003 (12)	−0.0168 (13)	−0.0156 (14)
O3W	0.0533 (16)	0.0606 (19)	0.084 (2)	0.0087 (15)	−0.0321 (14)	−0.0200 (16)

Geometric parameters (Å, º)

Pr1—O2	2.474 (2)	C16—H16A	0.9300
Pr1—O3	2.364 (2)	C17—H17A	0.9300
Pr1—O5	2.482 (2)	C18—H18A	0.9300
Pr1—O7	2.487 (2)	C19—C20	1.398 (5)
Pr1—O8	2.476 (2)	C19—H19A	0.9300
Pr1—N4	2.718 (2)	C20—C21	1.354 (5)
Pr1—N5	2.696 (2)	C20—H20A	0.9300
Pr1—N6	2.730 (2)	C21—C22	1.404 (5)
Pr1—N7	2.695 (2)	C21—H21A	0.9300
N1—C5	1.337 (5)	C22—C30	1.413 (4)
N1—C6	1.346 (4)	C22—C23	1.425 (5)
N2—C10	1.323 (5)	C23—C24	1.328 (5)
N2—C9	1.330 (4)	C23—H23A	0.9300
N3—C18	1.332 (4)	C24—C25	1.429 (5)
N3—C17	1.339 (5)	C24—H24A	0.9300
N4—C19	1.321 (4)	C25—C26	1.389 (5)
N4—C30	1.359 (3)	C25—C29	1.410 (4)
N5—C28	1.322 (4)	C26—C27	1.350 (5)
N5—C29	1.359 (4)	C26—H26A	0.9300
N6—C31	1.320 (4)	C27—C28	1.409 (5)
N6—C42	1.362 (3)	C27—H27A	0.9300
N7—C40	1.326 (4)	C28—H28A	0.9300
N7—C41	1.361 (4)	C29—C30	1.440 (4)
C1—O1	1.236 (4)	C31—C32	1.398 (4)
C1—O2	1.263 (3)	C31—H31A	0.9300
C1—C2	1.510 (4)	C32—C33	1.358 (4)
C2—C6	1.363 (4)	C32—H32A	0.9300
C2—C3	1.387 (4)	C33—C34	1.400 (4)
C3—C4	1.377 (5)	C33—H33A	0.9300
C3—H3A	0.9300	C34—C42	1.410 (4)
C4—C5	1.357 (6)	C34—C35	1.419 (4)
C4—H4A	0.9300	C35—C36	1.338 (5)
C5—H5A	0.9300	C35—H35A	0.9300
C6—H6A	0.9300	C36—C37	1.419 (4)
C7—O4	1.237 (3)	C36—H36A	0.9300
C7—O3	1.270 (3)	C37—C38	1.391 (4)
C7—C8	1.498 (4)	C37—C41	1.414 (4)
C8—C9	1.375 (4)	C38—C39	1.362 (5)
C8—C12	1.381 (4)	C38—H38A	0.9300
C9—H9A	0.9300	C39—C40	1.396 (4)
C10—C11	1.369 (5)	C39—H39A	0.9300
C10—H10A	0.9300	C40—H40A	0.9300
C11—C12	1.378 (5)	C41—C42	1.437 (4)
C11—H11A	0.9300	O7—H7A	0.832 (18)
C12—H12A	0.9300	O7—H7B	0.823 (19)
C13—O6	1.241 (4)	O8—H8A	0.831 (19)
C13—O5	1.270 (3)	O8—H8B	0.829 (19)
C13—C14	1.503 (4)	O1W—H1WA	0.836 (19)
C14—C15	1.374 (4)	O1W—H1WB	0.811 (19)
C14—C18	1.385 (5)	O2W—H2WA	0.827 (18)
C15—C16	1.380 (5)	O2W—H2WB	0.816 (18)
C15—H15A	0.9300	O3W—H3WA	0.816 (18)
C16—C17	1.360 (6)	O3W—H3WB	0.812 (19)
O3—Pr1—O2	78.19 (7)	C16—C15—H15A	120.5
O3—Pr1—O8	135.36 (7)	C17—C16—C15	118.3 (4)
O2—Pr1—O8	139.81 (8)	C17—C16—H16A	120.8
O3—Pr1—O5	88.14 (7)	C15—C16—H16A	120.8
O2—Pr1—O5	138.27 (7)	N3—C17—C16	124.6 (4)
O8—Pr1—O5	74.56 (8)	N3—C17—H17A	117.7
O3—Pr1—O7	141.56 (8)	C16—C17—H17A	117.7
O2—Pr1—O7	70.66 (7)	N3—C18—C14	123.9 (3)
O8—Pr1—O7	69.33 (8)	N3—C18—H18A	118.0
O5—Pr1—O7	130.20 (7)	C14—C18—H18A	118.0
O3—Pr1—N7	77.16 (7)	N4—C19—C20	124.3 (3)
O2—Pr1—N7	78.81 (7)	N4—C19—H19A	117.8
O8—Pr1—N7	87.57 (8)	C20—C19—H19A	117.8
O5—Pr1—N7	136.40 (7)	C21—C20—C19	119.0 (3)
O7—Pr1—N7	75.22 (8)	C21—C20—H20A	120.5
O3—Pr1—N5	131.85 (7)	C19—C20—H20A	120.5
O2—Pr1—N5	91.85 (7)	C20—C21—C22	119.3 (3)
O8—Pr1—N5	79.60 (8)	C20—C21—H21A	120.4
O5—Pr1—N5	68.47 (7)	C22—C21—H21A	120.4
O7—Pr1—N5	72.19 (8)	C21—C22—C30	117.8 (3)
N7—Pr1—N5	147.37 (8)	C21—C22—C23	122.3 (3)
O3—Pr1—N4	72.23 (7)	C30—C22—C23	119.9 (3)
O2—Pr1—N4	68.55 (7)	C24—C23—C22	120.6 (3)
O8—Pr1—N4	133.63 (8)	C24—C23—H23A	119.7
O5—Pr1—N4	69.74 (7)	C22—C23—H23A	119.7
O7—Pr1—N4	114.42 (8)	C23—C24—C25	121.9 (3)
N7—Pr1—N4	138.80 (7)	C23—C24—H24A	119.0
N5—Pr1—N4	60.45 (7)	C25—C24—H24A	119.0
O3—Pr1—N6	67.33 (7)	C26—C25—C29	116.8 (3)
O2—Pr1—N6	130.77 (7)	C26—C25—C24	123.7 (3)
O8—Pr1—N6	68.63 (8)	C29—C25—C24	119.5 (3)
O5—Pr1—N6	75.96 (7)	C27—C26—C25	120.9 (3)
O7—Pr1—N6	118.65 (8)	C27—C26—H26A	119.5
N7—Pr1—N6	60.48 (7)	C25—C26—H26A	119.5
N5—Pr1—N6	137.34 (7)	C26—C27—C28	118.5 (4)
N4—Pr1—N6	126.93 (7)	C26—C27—H27A	120.7
C5—N1—C6	116.2 (3)	C28—C27—H27A	120.7
C10—N2—C9	116.6 (3)	N5—C28—C27	123.2 (3)
C18—N3—C17	116.0 (4)	N5—C28—H28A	118.4
C19—N4—C30	117.0 (3)	C27—C28—H28A	118.4
C19—N4—Pr1	122.11 (19)	N5—C29—C25	123.0 (3)
C30—N4—Pr1	120.89 (18)	N5—C29—C30	118.2 (2)
C28—N5—C29	117.4 (3)	C25—C29—C30	118.8 (3)
C28—N5—Pr1	120.4 (2)	N4—C30—C22	122.6 (3)
C29—N5—Pr1	121.45 (19)	N4—C30—C29	118.2 (3)
C31—N6—C42	117.5 (2)	C22—C30—C29	119.2 (3)
C31—N6—Pr1	122.42 (18)	N6—C31—C32	124.0 (3)
C42—N6—Pr1	119.30 (18)	N6—C31—H31A	118.0
C40—N7—C41	117.6 (3)	C32—C31—H31A	118.0
C40—N7—Pr1	121.14 (19)	C33—C32—C31	118.7 (3)
C41—N7—Pr1	120.45 (18)	C33—C32—H32A	120.7
O1—C1—O2	125.5 (3)	C31—C32—H32A	120.7
O1—C1—C2	117.2 (3)	C32—C33—C34	119.7 (3)
O2—C1—C2	117.3 (3)	C32—C33—H33A	120.1
C6—C2—C3	117.8 (3)	C34—C33—H33A	120.1
C6—C2—C1	121.9 (3)	C33—C34—C42	117.8 (3)
C3—C2—C1	120.1 (3)	C33—C34—C35	122.5 (3)
C4—C3—C2	119.2 (4)	C42—C34—C35	119.7 (3)
C4—C3—H3A	120.4	C36—C35—C34	120.9 (3)
C2—C3—H3A	120.4	C36—C35—H35A	119.5
C5—C4—C3	118.6 (4)	C34—C35—H35A	119.5
C5—C4—H4A	120.7	C35—C36—C37	121.6 (3)
C3—C4—H4A	120.7	C35—C36—H36A	119.2
N1—C5—C4	124.1 (4)	C37—C36—H36A	119.2
N1—C5—H5A	117.9	C38—C37—C41	116.9 (3)
C4—C5—H5A	117.9	C38—C37—C36	123.5 (3)
N1—C6—C2	124.0 (3)	C41—C37—C36	119.6 (3)
N1—C6—H6A	118.0	C39—C38—C37	120.5 (3)
C2—C6—H6A	118.0	C39—C38—H38A	119.7
O4—C7—O3	124.8 (3)	C37—C38—H38A	119.7
O4—C7—C8	118.8 (3)	C38—C39—C40	118.7 (3)
O3—C7—C8	116.4 (3)	C38—C39—H39A	120.6
C9—C8—C12	117.2 (3)	C40—C39—H39A	120.6
C9—C8—C7	120.8 (3)	N7—C40—C39	123.4 (3)
C12—C8—C7	121.9 (3)	N7—C40—H40A	118.3
N2—C9—C8	124.8 (3)	C39—C40—H40A	118.3
N2—C9—H9A	117.6	N7—C41—C37	122.8 (3)
C8—C9—H9A	117.6	N7—C41—C42	118.4 (2)
N2—C10—C11	123.7 (3)	C37—C41—C42	118.7 (3)
N2—C10—H10A	118.2	N6—C42—C34	122.2 (3)
C11—C10—H10A	118.2	N6—C42—C41	118.4 (2)
C10—C11—C12	118.7 (3)	C34—C42—C41	119.5 (3)
C10—C11—H11A	120.6	C1—O2—Pr1	138.71 (19)
C12—C11—H11A	120.6	C7—O3—Pr1	152.62 (19)
C11—C12—C8	119.0 (3)	C13—O5—Pr1	131.47 (18)
C11—C12—H12A	120.5	Pr1—O7—H7A	112 (2)
C8—C12—H12A	120.5	Pr1—O7—H7B	141 (3)
O6—C13—O5	124.7 (3)	H7A—O7—H7B	102 (3)
O6—C13—C14	117.3 (3)	Pr1—O8—H8A	110 (3)
O5—C13—C14	118.0 (3)	Pr1—O8—H8B	145 (3)
C15—C14—C18	118.1 (3)	H8A—O8—H8B	103 (4)
C15—C14—C13	120.2 (3)	H1WA—O1W—H1WB	105 (3)
C18—C14—C13	121.7 (3)	H2WA—O2W—H2WB	108 (4)
C14—C15—C16	119.1 (4)	H3WA—O3W—H3WB	113 (4)
C14—C15—H15A	120.5
O3—Pr1—N4—C19	−12.5 (2)	N4—C19—C20—C21	−0.8 (6)
O2—Pr1—N4—C19	71.4 (2)	C19—C20—C21—C22	−1.1 (6)
O8—Pr1—N4—C19	−149.1 (2)	C20—C21—C22—C30	2.7 (5)
O5—Pr1—N4—C19	−107.2 (3)	C20—C21—C22—C23	−177.7 (3)
O7—Pr1—N4—C19	126.7 (2)	C21—C22—C23—C24	179.4 (4)
N7—Pr1—N4—C19	31.4 (3)	C30—C22—C23—C24	−1.0 (5)
N5—Pr1—N4—C19	176.7 (3)	C22—C23—C24—C25	2.6 (6)
N6—Pr1—N4—C19	−54.2 (3)	C23—C24—C25—C26	177.9 (4)
O3—Pr1—N4—C30	165.5 (2)	C23—C24—C25—C29	−1.1 (5)
O2—Pr1—N4—C30	−110.5 (2)	C29—C25—C26—C27	1.8 (5)
O8—Pr1—N4—C30	28.9 (2)	C24—C25—C26—C27	−177.3 (3)
O5—Pr1—N4—C30	70.8 (2)	C25—C26—C27—C28	0.4 (6)
O7—Pr1—N4—C30	−55.2 (2)	C29—N5—C28—C27	1.6 (5)
N7—Pr1—N4—C30	−150.61 (18)	Pr1—N5—C28—C27	−168.5 (3)
N5—Pr1—N4—C30	−5.31 (19)	C26—C27—C28—N5	−2.2 (5)
N6—Pr1—N4—C30	123.8 (2)	C28—N5—C29—C25	0.8 (4)
O3—Pr1—N5—C28	166.0 (2)	Pr1—N5—C29—C25	170.8 (2)
O2—Pr1—N5—C28	−118.2 (2)	C28—N5—C29—C30	179.4 (3)
O8—Pr1—N5—C28	22.2 (2)	Pr1—N5—C29—C30	−10.6 (3)
O5—Pr1—N5—C28	99.6 (2)	C26—C25—C29—N5	−2.5 (5)
O7—Pr1—N5—C28	−49.2 (2)	C24—C25—C29—N5	176.6 (3)
N7—Pr1—N5—C28	−46.2 (3)	C26—C25—C29—C30	178.9 (3)
N4—Pr1—N5—C28	177.8 (3)	C24—C25—C29—C30	−2.0 (4)
N6—Pr1—N5—C28	64.0 (3)	C19—N4—C30—C22	1.1 (4)
O3—Pr1—N5—C29	−3.6 (2)	Pr1—N4—C30—C22	−177.0 (2)
O2—Pr1—N5—C29	72.1 (2)	C19—N4—C30—C29	−179.3 (3)
O8—Pr1—N5—C29	−147.4 (2)	Pr1—N4—C30—C29	2.6 (3)
O5—Pr1—N5—C29	−70.0 (2)	C21—C22—C30—N4	−2.8 (4)
O7—Pr1—N5—C29	141.1 (2)	C23—C22—C30—N4	177.6 (3)
N7—Pr1—N5—C29	144.1 (2)	C21—C22—C30—C29	177.6 (3)
N4—Pr1—N5—C29	8.2 (2)	C23—C22—C30—C29	−2.0 (4)
N6—Pr1—N5—C29	−105.6 (2)	N5—C29—C30—N4	5.2 (4)
O3—Pr1—N6—C31	−95.8 (2)	C25—C29—C30—N4	−176.1 (3)
O2—Pr1—N6—C31	−145.0 (2)	N5—C29—C30—C22	−175.2 (3)
O8—Pr1—N6—C31	76.8 (2)	C25—C29—C30—C22	3.5 (4)
O5—Pr1—N6—C31	−1.9 (2)	C42—N6—C31—C32	−0.5 (4)
O7—Pr1—N6—C31	126.6 (2)	Pr1—N6—C31—C32	169.4 (2)
N7—Pr1—N6—C31	176.5 (2)	N6—C31—C32—C33	−0.5 (5)
N5—Pr1—N6—C31	32.1 (3)	C31—C32—C33—C34	0.8 (5)
N4—Pr1—N6—C31	−52.5 (2)	C32—C33—C34—C42	0.0 (5)
O3—Pr1—N6—C42	74.00 (19)	C32—C33—C34—C35	179.2 (3)
O2—Pr1—N6—C42	24.8 (2)	C33—C34—C35—C36	−177.8 (3)
O8—Pr1—N6—C42	−113.4 (2)	C42—C34—C35—C36	1.4 (5)
O5—Pr1—N6—C42	167.9 (2)	C34—C35—C36—C37	0.6 (5)
O7—Pr1—N6—C42	−63.7 (2)	C35—C36—C37—C38	176.2 (3)
N7—Pr1—N6—C42	−13.69 (18)	C35—C36—C37—C41	−2.0 (5)
N5—Pr1—N6—C42	−158.15 (18)	C41—C37—C38—C39	2.3 (5)
N4—Pr1—N6—C42	117.31 (19)	C36—C37—C38—C39	−176.0 (3)
O3—Pr1—N7—C40	112.9 (3)	C37—C38—C39—C40	−3.4 (5)
O2—Pr1—N7—C40	32.6 (2)	C41—N7—C40—C39	1.3 (5)
O8—Pr1—N7—C40	−109.4 (3)	Pr1—N7—C40—C39	−168.4 (3)
O5—Pr1—N7—C40	−173.8 (2)	C38—C39—C40—N7	1.6 (6)
O7—Pr1—N7—C40	−40.1 (2)	C40—N7—C41—C37	−2.5 (4)
N5—Pr1—N7—C40	−43.0 (3)	Pr1—N7—C41—C37	167.2 (2)
N4—Pr1—N7—C40	70.2 (3)	C40—N7—C41—C42	175.3 (3)
N6—Pr1—N7—C40	−176.1 (3)	Pr1—N7—C41—C42	−14.9 (3)
O3—Pr1—N7—C41	−56.5 (2)	C38—C37—C41—N7	0.8 (4)
O2—Pr1—N7—C41	−136.8 (2)	C36—C37—C41—N7	179.1 (3)
O8—Pr1—N7—C41	81.2 (2)	C38—C37—C41—C42	−177.1 (3)
O5—Pr1—N7—C41	16.8 (3)	C36—C37—C41—C42	1.3 (4)
O7—Pr1—N7—C41	150.5 (2)	C31—N6—C42—C34	1.4 (4)
N5—Pr1—N7—C41	147.56 (19)	Pr1—N6—C42—C34	−168.9 (2)
N4—Pr1—N7—C41	−99.2 (2)	C31—N6—C42—C41	−177.0 (3)
N6—Pr1—N7—C41	14.50 (19)	Pr1—N6—C42—C41	12.8 (3)
O1—C1—C2—C6	−179.5 (3)	C33—C34—C42—N6	−1.1 (4)
O2—C1—C2—C6	−0.8 (4)	C35—C34—C42—N6	179.6 (3)
O1—C1—C2—C3	−3.9 (4)	C33—C34—C42—C41	177.2 (3)
O2—C1—C2—C3	174.7 (3)	C35—C34—C42—C41	−2.0 (4)
C6—C2—C3—C4	1.2 (5)	N7—C41—C42—N6	1.2 (4)
C1—C2—C3—C4	−174.5 (3)	C37—C41—C42—N6	179.1 (3)
C2—C3—C4—C5	0.6 (6)	N7—C41—C42—C34	−177.2 (3)
C6—N1—C5—C4	0.9 (6)	C37—C41—C42—C34	0.7 (4)
C3—C4—C5—N1	−1.7 (6)	O1—C1—O2—Pr1	35.1 (5)
C5—N1—C6—C2	1.1 (5)	C2—C1—O2—Pr1	−143.4 (2)
C3—C2—C6—N1	−2.2 (5)	O3—Pr1—O2—C1	−179.8 (3)
C1—C2—C6—N1	173.5 (3)	O8—Pr1—O2—C1	−28.3 (3)
O4—C7—C8—C9	−17.6 (5)	O5—Pr1—O2—C1	106.7 (3)
O3—C7—C8—C9	162.5 (3)	O7—Pr1—O2—C1	−22.6 (3)
O4—C7—C8—C12	166.6 (3)	N7—Pr1—O2—C1	−100.8 (3)
O3—C7—C8—C12	−13.3 (4)	N5—Pr1—O2—C1	47.7 (3)
C10—N2—C9—C8	−1.4 (7)	N4—Pr1—O2—C1	104.8 (3)
C12—C8—C9—N2	−0.6 (6)	N6—Pr1—O2—C1	−134.3 (3)
C7—C8—C9—N2	−176.6 (4)	O4—C7—O3—Pr1	92.0 (5)
C9—N2—C10—C11	3.1 (7)	C8—C7—O3—Pr1	−88.1 (5)
N2—C10—C11—C12	−2.5 (7)	O2—Pr1—O3—C7	123.2 (4)
C10—C11—C12—C8	0.3 (6)	O8—Pr1—O3—C7	−30.9 (5)
C9—C8—C12—C11	1.2 (5)	O5—Pr1—O3—C7	−96.5 (4)
C7—C8—C12—C11	177.2 (3)	O7—Pr1—O3—C7	87.0 (4)
O6—C13—C14—C15	−1.6 (4)	N7—Pr1—O3—C7	42.1 (4)
O5—C13—C14—C15	179.5 (3)	N5—Pr1—O3—C7	−155.1 (4)
O6—C13—C14—C18	175.6 (3)	N4—Pr1—O3—C7	−165.8 (4)
O5—C13—C14—C18	−3.3 (4)	N6—Pr1—O3—C7	−21.0 (4)
C18—C14—C15—C16	1.3 (5)	O6—C13—O5—Pr1	−40.1 (4)
C13—C14—C15—C16	178.6 (3)	C14—C13—O5—Pr1	138.6 (2)
C14—C15—C16—C17	−1.6 (6)	O3—Pr1—O5—C13	169.2 (2)
C18—N3—C17—C16	0.7 (7)	O2—Pr1—O5—C13	−120.9 (2)
C15—C16—C17—N3	0.6 (8)	O8—Pr1—O5—C13	30.8 (2)
C17—N3—C18—C14	−1.0 (6)	O7—Pr1—O5—C13	−13.7 (3)
C15—C14—C18—N3	0.0 (6)	N7—Pr1—O5—C13	100.1 (2)
C13—C14—C18—N3	−177.2 (3)	N5—Pr1—O5—C13	−53.9 (2)
C30—N4—C19—C20	0.7 (5)	N4—Pr1—O5—C13	−119.1 (2)
Pr1—N4—C19—C20	178.8 (3)	N6—Pr1—O5—C13	102.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2W—H2WA···O4^i	0.83 (2)	1.91 (2)	2.729 (3)	171 (4)
O2W—H2WB···O5^i	0.82 (3)	2.09 (2)	2.894 (3)	169 (4)
O3W—H3WA···O2W	0.81 (4)	1.99 (2)	2.784 (4)	164 (4)
O3W—H3WB···O1W^ii	0.81 (3)	1.96 (2)	2.771 (4)	179 (4)
O7—H7A···O1	0.83 (2)	1.82 (2)	2.626 (3)	164 (3)

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x+1, y−1, z.