The Pr atom in the title complex, [Pr(NO3)3(C10H8N8)(H2O)2]·1.5C10H8N2, is ten-coordinate and the relative arrangement of the ligands in the first coordination sphere is affected by the hydrogen bonds between the coordinated water molecules and the uncoordinated 2,2′-bipyridyl (bipy) solvent molecules, one of which lies on a cystallographic inversion centre.
Supporting information
CCDC reference: 252767
Key indicators
- Single-crystal X-ray study
- T = 130 K
- R factor = 0.038
- wR factor = 0.084
- Data-to-parameter ratio = 15.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Pr - O31 .. 6.13 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Pr - O41 .. 5.38 su
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 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
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: KappaCCD Software (Nonius, 1997); cell refinement: HKL (Otwinowski & Minor, 1997); data reduction: HKL; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); ORTEP-3 for Windows (Farrugia, 1997)
CAMERON (Watkin et al., 1993); software used to prepare material for publication: SHELXTL (Sheldrick, 1997).
(2,2'-bipyridyl)-diaqua-tris(nitrato-O,
O')-praseodymium(III) bipyridyl
1.5 solvate
top
Crystal data top
C10H12N5O11Pr·1.5(C10H8N2) | Z = 2 |
Mr = 753.43 | F(000) = 754 |
Triclinic, P1 | Dx = 1.721 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.4160 (5) Å | Cell parameters from 13117 reflections |
b = 11.4284 (6) Å | θ = 2–27.5° |
c = 14.0585 (10) Å | µ = 1.75 mm−1 |
α = 75.322 (4)° | T = 130 K |
β = 81.118 (4)° | Prism, green |
γ = 64.060 (4)° | 0.27 × 0.27 × 0.18 mm |
V = 1453.96 (15) Å3 | |
Data collection top
Nonius KappaCCD diffractometer | 6527 independent reflections |
Radiation source: fine-focus sealed tube | 6042 reflections with I > 2s˘I) |
Graphite monochromator | Rint = 0.045 |
φ– ω–scans to cover a hemisphere of the reciprocal space | θmax = 27.5°, θmin = 2.3° |
Absorption correction: multi-scan 'MULABS (Blessing, 1995)' | h = −13→13 |
Tmin = 0.659, Tmax = 0.732 | k = −13→14 |
13117 measured reflections | l = −16→18 |
Refinement top
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.085 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.P)2 + 3.9292P] where P = (Fo2 + 2Fc2)/3 |
6527 reflections | (Δ/σ)max = 0.003 |
418 parameters | Δρmax = 1.14 e Å−3 |
6 restraints | Δρmin = −1.89 e Å−3 |
Special details top
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 on F2 for ALL reflections except for 18 flagged for
potential systematic errors |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Pr | 0.817210 (18) | 0.458632 (16) | 0.214690 (13) | 0.01378 (6) | |
N1 | 0.6049 (3) | 0.4018 (3) | 0.3146 (2) | 0.0195 (6) | |
N2 | 0.8210 (3) | 0.3824 (3) | 0.4110 (2) | 0.0182 (6) | |
N3 | 0.6632 (3) | 0.5196 (3) | 0.0328 (2) | 0.0208 (6) | |
N4 | 1.1355 (3) | 0.3138 (3) | 0.1794 (2) | 0.0211 (6) | |
N5 | 0.7219 (4) | 0.6940 (3) | 0.3082 (2) | 0.0240 (7) | |
N6 | 0.7965 (3) | 0.8730 (3) | 0.1050 (2) | 0.0201 (6) | |
N7 | 1.0361 (3) | 1.0065 (3) | 0.1467 (2) | 0.0212 (6) | |
N8 | 0.8767 (4) | 0.0318 (3) | 0.4093 (3) | 0.0256 (7) | |
O1W | 0.8895 (3) | 0.6168 (2) | 0.0898 (2) | 0.0222 (5) | |
H11 | 0.900 (5) | 0.613 (4) | 0.0298 (17) | 0.033* | |
H12 | 0.875 (5) | 0.694 (3) | 0.095 (3) | 0.033* | |
O2W | 0.8921 (3) | 0.2167 (2) | 0.2444 (2) | 0.0209 (5) | |
H21 | 0.885 (5) | 0.167 (4) | 0.2999 (18) | 0.031* | |
H22 | 0.929 (5) | 0.172 (4) | 0.201 (2) | 0.031* | |
O31 | 0.6090 (3) | 0.5928 (2) | 0.0957 (2) | 0.0251 (6) | |
O32 | 0.7726 (3) | 0.4127 (2) | 0.0578 (2) | 0.0264 (6) | |
O33 | 0.6140 (4) | 0.5494 (3) | −0.0477 (2) | 0.0382 (7) | |
O41 | 1.0510 (3) | 0.3368 (2) | 0.1136 (2) | 0.0220 (5) | |
O42 | 1.0794 (3) | 0.3644 (3) | 0.2545 (2) | 0.0237 (5) | |
O43 | 1.2629 (3) | 0.2427 (3) | 0.1735 (3) | 0.0400 (8) | |
O51 | 0.6324 (3) | 0.6621 (2) | 0.2806 (2) | 0.0254 (6) | |
O52 | 0.8531 (3) | 0.6246 (3) | 0.2910 (2) | 0.0247 (5) | |
O53 | 0.6819 (4) | 0.7871 (3) | 0.3497 (3) | 0.0414 (8) | |
C1 | 0.4990 (4) | 0.4112 (4) | 0.2650 (3) | 0.0272 (8) | |
H1 | 0.5033 | 0.4374 | 0.1967 | 0.033* | |
C2 | 0.3836 (4) | 0.3840 (4) | 0.3097 (4) | 0.0311 (9) | |
H2 | 0.3125 | 0.3921 | 0.2726 | 0.037* | |
C3 | 0.3780 (4) | 0.3445 (4) | 0.4108 (3) | 0.0308 (9) | |
H3 | 0.3020 | 0.3260 | 0.4433 | 0.037* | |
C4 | 0.4864 (4) | 0.3327 (4) | 0.4638 (3) | 0.0255 (8) | |
H4 | 0.4845 | 0.3054 | 0.5320 | 0.031* | |
C5 | 0.5985 (4) | 0.3624 (3) | 0.4134 (3) | 0.0192 (7) | |
C6 | 0.7183 (4) | 0.3506 (3) | 0.4664 (3) | 0.0177 (7) | |
C7 | 0.7250 (4) | 0.3082 (4) | 0.5689 (3) | 0.0267 (8) | |
H7 | 0.6538 | 0.2861 | 0.6062 | 0.032* | |
C8 | 0.8386 (5) | 0.2994 (4) | 0.6142 (3) | 0.0309 (9) | |
H8 | 0.8449 | 0.2709 | 0.6821 | 0.037* | |
C9 | 0.9426 (4) | 0.3334 (4) | 0.5575 (3) | 0.0273 (8) | |
H9 | 1.0197 | 0.3287 | 0.5864 | 0.033* | |
C10 | 0.9297 (4) | 0.3744 (4) | 0.4574 (3) | 0.0222 (7) | |
H10 | 0.9996 | 0.3979 | 0.4196 | 0.027* | |
C11 | 0.6563 (4) | 0.9083 (4) | 0.0995 (3) | 0.0234 (7) | |
H11A | 0.6278 | 0.8454 | 0.0906 | 0.028* | |
C12 | 0.5521 (4) | 1.0336 (4) | 0.1065 (3) | 0.0253 (8) | |
H12A | 0.4558 | 1.0539 | 0.1037 | 0.030* | |
C13 | 0.5948 (4) | 1.1277 (4) | 0.1177 (3) | 0.0263 (8) | |
H13 | 0.5275 | 1.2128 | 0.1225 | 0.032* | |
C14 | 0.7396 (4) | 1.0937 (3) | 0.1216 (3) | 0.0239 (8) | |
H14 | 0.7703 | 1.1566 | 0.1275 | 0.029* | |
C15 | 0.8388 (4) | 0.9642 (3) | 0.1167 (3) | 0.0181 (7) | |
C16 | 0.9951 (4) | 0.9215 (3) | 0.1225 (3) | 0.0178 (6) | |
C17 | 1.0954 (4) | 0.7983 (3) | 0.1036 (3) | 0.0215 (7) | |
H17 | 1.0658 | 0.7411 | 0.0859 | 0.026* | |
C18 | 1.2395 (4) | 0.7626 (4) | 0.1115 (3) | 0.0252 (8) | |
H18 | 1.3074 | 0.6810 | 0.0996 | 0.030* | |
C19 | 1.2813 (4) | 0.8493 (4) | 0.1371 (3) | 0.0257 (8) | |
H19 | 1.3772 | 0.8270 | 0.1436 | 0.031* | |
C20 | 1.1761 (4) | 0.9703 (4) | 0.1528 (3) | 0.0249 (8) | |
H20 | 1.2041 | 1.0298 | 0.1685 | 0.030* | |
C21 | 0.7612 (4) | 0.0135 (4) | 0.4011 (3) | 0.0285 (8) | |
H21A | 0.7243 | 0.0387 | 0.3393 | 0.034* | |
C22 | 0.6933 (4) | −0.0414 (4) | 0.4805 (3) | 0.0283 (8) | |
H22A | 0.6153 | −0.0559 | 0.4716 | 0.034* | |
C23 | 0.7442 (4) | −0.0737 (4) | 0.5727 (3) | 0.0312 (9) | |
H23 | 0.6980 | −0.1062 | 0.6278 | 0.037* | |
C24 | 0.8666 (4) | −0.0569 (4) | 0.5820 (3) | 0.0263 (8) | |
H24 | 0.9032 | −0.0786 | 0.6435 | 0.032* | |
C25 | 0.9329 (4) | −0.0074 (3) | 0.4983 (3) | 0.0210 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Pr | 0.01442 (10) | 0.01375 (10) | 0.01467 (10) | −0.00648 (7) | −0.00097 (6) | −0.00419 (7) |
N1 | 0.0205 (14) | 0.0205 (14) | 0.0213 (15) | −0.0106 (12) | 0.0002 (11) | −0.0079 (12) |
N2 | 0.0201 (14) | 0.0190 (13) | 0.0161 (14) | −0.0073 (12) | −0.0009 (11) | −0.0063 (11) |
N3 | 0.0267 (15) | 0.0166 (13) | 0.0202 (15) | −0.0085 (12) | −0.0086 (12) | −0.0022 (11) |
N4 | 0.0186 (14) | 0.0206 (14) | 0.0274 (17) | −0.0106 (12) | 0.0023 (12) | −0.0081 (12) |
N5 | 0.0367 (17) | 0.0224 (15) | 0.0193 (16) | −0.0174 (14) | 0.0042 (13) | −0.0085 (12) |
N6 | 0.0179 (13) | 0.0168 (13) | 0.0258 (16) | −0.0073 (11) | −0.0027 (12) | −0.0039 (12) |
N7 | 0.0203 (14) | 0.0182 (14) | 0.0280 (17) | −0.0090 (12) | −0.0008 (12) | −0.0076 (12) |
N8 | 0.0305 (16) | 0.0258 (15) | 0.0242 (17) | −0.0150 (14) | −0.0015 (13) | −0.0052 (13) |
O1W | 0.0314 (13) | 0.0174 (11) | 0.0202 (13) | −0.0134 (11) | 0.0034 (11) | −0.0048 (10) |
O2W | 0.0292 (13) | 0.0141 (11) | 0.0182 (13) | −0.0081 (10) | 0.0001 (10) | −0.0038 (9) |
O31 | 0.0205 (12) | 0.0232 (12) | 0.0300 (15) | −0.0043 (10) | −0.0033 (11) | −0.0109 (11) |
O32 | 0.0293 (14) | 0.0195 (12) | 0.0265 (15) | −0.0004 (11) | −0.0124 (11) | −0.0098 (11) |
O33 | 0.0555 (19) | 0.0293 (14) | 0.0286 (16) | −0.0119 (14) | −0.0258 (15) | −0.0007 (12) |
O41 | 0.0218 (12) | 0.0261 (12) | 0.0205 (13) | −0.0111 (10) | 0.0000 (10) | −0.0073 (10) |
O42 | 0.0180 (12) | 0.0279 (13) | 0.0263 (14) | −0.0080 (10) | −0.0001 (10) | −0.0112 (11) |
O43 | 0.0138 (12) | 0.0480 (18) | 0.059 (2) | −0.0055 (13) | 0.0030 (13) | −0.0296 (17) |
O51 | 0.0255 (13) | 0.0234 (12) | 0.0317 (15) | −0.0112 (11) | 0.0021 (11) | −0.0135 (11) |
O52 | 0.0273 (13) | 0.0249 (13) | 0.0278 (15) | −0.0144 (11) | −0.0006 (11) | −0.0094 (11) |
O53 | 0.063 (2) | 0.0366 (16) | 0.0383 (18) | −0.0298 (16) | 0.0154 (16) | −0.0252 (14) |
C1 | 0.0250 (18) | 0.036 (2) | 0.028 (2) | −0.0168 (16) | −0.0035 (15) | −0.0093 (16) |
C2 | 0.0269 (19) | 0.032 (2) | 0.044 (3) | −0.0183 (17) | −0.0043 (17) | −0.0123 (18) |
C3 | 0.0253 (18) | 0.033 (2) | 0.042 (2) | −0.0193 (17) | 0.0070 (17) | −0.0122 (18) |
C4 | 0.0271 (18) | 0.0269 (18) | 0.0240 (19) | −0.0140 (16) | 0.0042 (15) | −0.0059 (15) |
C5 | 0.0208 (16) | 0.0140 (15) | 0.0234 (18) | −0.0077 (13) | 0.0028 (13) | −0.0067 (13) |
C6 | 0.0205 (16) | 0.0129 (14) | 0.0195 (17) | −0.0061 (13) | 0.0009 (13) | −0.0060 (12) |
C7 | 0.035 (2) | 0.0280 (18) | 0.0195 (19) | −0.0172 (17) | 0.0018 (15) | −0.0033 (15) |
C8 | 0.042 (2) | 0.033 (2) | 0.0156 (18) | −0.0139 (18) | −0.0047 (16) | −0.0021 (15) |
C9 | 0.031 (2) | 0.0271 (18) | 0.025 (2) | −0.0094 (16) | −0.0103 (16) | −0.0075 (15) |
C10 | 0.0214 (17) | 0.0244 (17) | 0.0238 (19) | −0.0106 (14) | −0.0024 (14) | −0.0071 (14) |
C11 | 0.0211 (17) | 0.0205 (16) | 0.031 (2) | −0.0108 (14) | −0.0019 (14) | −0.0048 (15) |
C12 | 0.0153 (16) | 0.0262 (18) | 0.033 (2) | −0.0069 (14) | −0.0011 (14) | −0.0077 (16) |
C13 | 0.0189 (17) | 0.0197 (17) | 0.036 (2) | −0.0012 (14) | −0.0042 (15) | −0.0093 (16) |
C14 | 0.0224 (17) | 0.0160 (16) | 0.034 (2) | −0.0057 (14) | −0.0050 (15) | −0.0080 (15) |
C15 | 0.0184 (16) | 0.0161 (15) | 0.0196 (17) | −0.0066 (13) | −0.0015 (13) | −0.0043 (13) |
C16 | 0.0203 (16) | 0.0158 (15) | 0.0172 (16) | −0.0067 (13) | −0.0023 (13) | −0.0040 (12) |
C17 | 0.0209 (16) | 0.0185 (16) | 0.0265 (19) | −0.0080 (14) | −0.0007 (14) | −0.0076 (14) |
C18 | 0.0199 (17) | 0.0209 (17) | 0.031 (2) | −0.0031 (14) | −0.0005 (15) | −0.0086 (15) |
C19 | 0.0173 (16) | 0.0293 (19) | 0.031 (2) | −0.0096 (15) | −0.0006 (14) | −0.0076 (16) |
C20 | 0.0213 (17) | 0.0279 (18) | 0.032 (2) | −0.0137 (15) | 0.0000 (15) | −0.0120 (16) |
C21 | 0.032 (2) | 0.0289 (19) | 0.028 (2) | −0.0144 (17) | −0.0042 (16) | −0.0064 (16) |
C22 | 0.0242 (18) | 0.0260 (18) | 0.037 (2) | −0.0113 (16) | −0.0014 (16) | −0.0083 (17) |
C23 | 0.030 (2) | 0.031 (2) | 0.033 (2) | −0.0166 (17) | 0.0035 (17) | −0.0036 (17) |
C24 | 0.0291 (19) | 0.0289 (19) | 0.0219 (19) | −0.0146 (16) | −0.0015 (15) | −0.0021 (15) |
C25 | 0.0234 (17) | 0.0134 (15) | 0.0261 (19) | −0.0069 (14) | −0.0008 (14) | −0.0051 (13) |
Geometric parameters (Å, º) top
Pr—O2W | 2.461 (2) | C3—C4 | 1.387 (6) |
Pr—O1W | 2.468 (2) | C3—H3 | 0.9300 |
Pr—O32 | 2.544 (3) | C4—C5 | 1.397 (5) |
Pr—O42 | 2.554 (2) | C4—H4 | 0.9300 |
Pr—O51 | 2.568 (2) | C5—C6 | 1.489 (5) |
Pr—O52 | 2.582 (3) | C6—C7 | 1.402 (5) |
Pr—O31 | 2.601 (3) | C7—C8 | 1.383 (6) |
Pr—O41 | 2.618 (2) | C7—H7 | 0.9300 |
Pr—N1 | 2.668 (3) | C8—C9 | 1.380 (6) |
Pr—N2 | 2.676 (3) | C8—H8 | 0.9300 |
Pr—N3 | 2.997 (3) | C9—C10 | 1.373 (6) |
Pr—N4 | 3.014 (3) | C9—H9 | 0.9300 |
Pr—N5 | 3.000 (3) | C10—H10 | 0.9300 |
N1—C1 | 1.346 (5) | C11—C12 | 1.385 (5) |
N1—C5 | 1.347 (5) | C11—H11A | 0.9300 |
N2—C10 | 1.351 (5) | C12—C13 | 1.380 (5) |
N2—C6 | 1.351 (4) | C12—H12A | 0.9300 |
N3—O33 | 1.220 (4) | C13—C14 | 1.390 (5) |
N3—O32 | 1.266 (4) | C13—H13 | 0.9300 |
N3—O31 | 1.268 (4) | C14—C15 | 1.398 (5) |
N4—O43 | 1.218 (4) | C14—H14 | 0.9300 |
N4—O42 | 1.271 (4) | C15—C16 | 1.490 (5) |
N4—O41 | 1.274 (4) | C16—C17 | 1.401 (5) |
N5—O53 | 1.224 (4) | C17—C18 | 1.387 (5) |
N5—O52 | 1.266 (4) | C17—H17 | 0.9300 |
N5—O51 | 1.278 (4) | C18—C19 | 1.380 (6) |
N6—C11 | 1.344 (5) | C18—H18 | 0.9300 |
N6—C15 | 1.349 (4) | C19—C20 | 1.384 (5) |
N7—C20 | 1.340 (5) | C19—H19 | 0.9300 |
N7—C16 | 1.348 (4) | C20—H20 | 0.9300 |
N8—C21 | 1.334 (5) | C21—C22 | 1.388 (6) |
N8—C25 | 1.350 (5) | C21—H21A | 0.9300 |
O1W—H11 | 0.85 (2) | C22—C23 | 1.376 (6) |
O1W—H12 | 0.85 (4) | C22—H22A | 0.9300 |
O2W—H21 | 0.86 (2) | C23—C24 | 1.399 (6) |
O2W—H22 | 0.83 (4) | C23—H23 | 0.9300 |
C1—C2 | 1.390 (5) | C24—C25 | 1.391 (5) |
C1—H1 | 0.9300 | C24—H24 | 0.9300 |
C2—C3 | 1.379 (7) | C25—C25i | 1.488 (7) |
C2—H2 | 0.9300 | | |
| | | |
O2W—Pr—O1W | 133.48 (8) | C11—N6—C15 | 118.7 (3) |
O2W—Pr—O32 | 73.82 (9) | C20—N7—C16 | 118.4 (3) |
O1W—Pr—O32 | 79.68 (9) | C21—N8—C25 | 118.8 (3) |
O2W—Pr—O42 | 77.04 (8) | Pr—O1W—H11 | 120 (3) |
O1W—Pr—O42 | 80.96 (9) | Pr—O1W—H12 | 126 (3) |
O32—Pr—O42 | 115.42 (8) | H11—O1W—H12 | 110 (3) |
O2W—Pr—O51 | 139.96 (9) | Pr—O2W—H21 | 126 (3) |
O1W—Pr—O51 | 86.45 (9) | Pr—O2W—H22 | 124 (3) |
O32—Pr—O51 | 119.66 (8) | H21—O2W—H22 | 110 (3) |
O42—Pr—O51 | 119.77 (8) | N3—O31—Pr | 95.32 (18) |
O2W—Pr—O52 | 137.80 (9) | N3—O32—Pr | 98.10 (19) |
O1W—Pr—O52 | 67.69 (9) | N4—O41—Pr | 95.23 (19) |
O32—Pr—O52 | 145.53 (9) | N4—O42—Pr | 98.4 (2) |
O42—Pr—O52 | 71.15 (8) | N5—O51—Pr | 96.77 (19) |
O51—Pr—O52 | 49.80 (8) | N5—O52—Pr | 96.43 (19) |
O2W—Pr—O31 | 112.91 (9) | N1—C1—C2 | 123.8 (4) |
O1W—Pr—O31 | 73.63 (9) | N1—C1—H1 | 118.1 |
O32—Pr—O31 | 49.45 (8) | C2—C1—H1 | 118.1 |
O42—Pr—O31 | 152.21 (9) | C3—C2—C1 | 117.9 (4) |
O51—Pr—O31 | 70.26 (8) | C3—C2—H2 | 121.0 |
O52—Pr—O31 | 108.13 (8) | C1—C2—H2 | 121.0 |
O2W—Pr—O41 | 66.49 (8) | C2—C3—C4 | 119.5 (4) |
O1W—Pr—O41 | 68.00 (8) | C2—C3—H3 | 120.3 |
O32—Pr—O41 | 66.12 (8) | C4—C3—H3 | 120.3 |
O42—Pr—O41 | 49.48 (8) | C3—C4—C5 | 119.1 (4) |
O51—Pr—O41 | 152.89 (8) | C3—C4—H4 | 120.4 |
O52—Pr—O41 | 109.01 (8) | C5—C4—H4 | 120.4 |
O31—Pr—O41 | 108.87 (8) | N1—C5—C4 | 122.0 (3) |
O2W—Pr—N1 | 71.51 (9) | N1—C5—C6 | 116.6 (3) |
O1W—Pr—N1 | 147.80 (9) | C4—C5—C6 | 121.4 (3) |
O32—Pr—N1 | 92.22 (9) | N2—C6—C7 | 121.2 (3) |
O42—Pr—N1 | 129.77 (9) | N2—C6—C5 | 116.9 (3) |
O51—Pr—N1 | 70.50 (9) | C7—C6—C5 | 121.9 (3) |
O52—Pr—N1 | 109.31 (9) | C8—C7—C6 | 119.4 (4) |
O31—Pr—N1 | 77.47 (9) | C8—C7—H7 | 120.3 |
O41—Pr—N1 | 136.53 (8) | C6—C7—H7 | 120.3 |
O2W—Pr—N2 | 76.33 (9) | C9—C8—C7 | 119.3 (4) |
O1W—Pr—N2 | 135.15 (9) | C9—C8—H8 | 120.3 |
O32—Pr—N2 | 144.92 (9) | C7—C8—H8 | 120.3 |
O42—Pr—N2 | 74.52 (9) | C10—C9—C8 | 118.5 (4) |
O51—Pr—N2 | 74.53 (9) | C10—C9—H9 | 120.7 |
O52—Pr—N2 | 69.05 (9) | C8—C9—H9 | 120.7 |
O31—Pr—N2 | 132.22 (9) | N2—C10—C9 | 123.6 (4) |
O41—Pr—N2 | 117.12 (8) | N2—C10—H10 | 118.2 |
N1—Pr—N2 | 60.75 (9) | C9—C10—H10 | 118.2 |
O2W—Pr—N3 | 94.79 (8) | N6—C11—C12 | 123.3 (3) |
O1W—Pr—N3 | 73.04 (9) | N6—C11—H11A | 118.4 |
O32—Pr—N3 | 24.73 (8) | C12—C11—H11A | 118.4 |
O42—Pr—N3 | 134.82 (9) | C13—C12—C11 | 118.3 (3) |
O51—Pr—N3 | 95.14 (9) | C13—C12—H12A | 120.9 |
O52—Pr—N3 | 127.33 (8) | C11—C12—H12A | 120.9 |
O31—Pr—N3 | 24.92 (8) | C12—C13—C14 | 119.2 (3) |
O41—Pr—N3 | 86.23 (8) | C12—C13—H13 | 120.4 |
N1—Pr—N3 | 86.58 (9) | C14—C13—H13 | 120.4 |
N2—Pr—N3 | 147.33 (9) | C13—C14—C15 | 119.5 (3) |
O2W—Pr—N5 | 145.52 (9) | C13—C14—H14 | 120.2 |
O1W—Pr—N5 | 76.44 (9) | C15—C14—H14 | 120.2 |
O32—Pr—N5 | 137.22 (8) | N6—C15—C14 | 121.0 (3) |
O42—Pr—N5 | 95.25 (9) | N6—C15—C16 | 117.2 (3) |
O51—Pr—N5 | 25.02 (9) | C14—C15—C16 | 121.8 (3) |
O52—Pr—N5 | 24.80 (9) | N7—C16—C17 | 121.3 (3) |
O31—Pr—N5 | 89.64 (9) | N7—C16—C15 | 117.2 (3) |
O41—Pr—N5 | 132.25 (8) | C17—C16—C15 | 121.5 (3) |
N1—Pr—N5 | 89.61 (9) | C18—C17—C16 | 119.1 (3) |
N2—Pr—N5 | 69.24 (9) | C18—C17—H17 | 120.5 |
N3—Pr—N5 | 113.09 (9) | C16—C17—H17 | 120.5 |
C1—N1—C5 | 117.7 (3) | C19—C18—C17 | 119.6 (3) |
C1—N1—Pr | 119.2 (3) | C19—C18—H18 | 120.2 |
C5—N1—Pr | 123.2 (2) | C17—C18—H18 | 120.2 |
C10—N2—C6 | 118.0 (3) | C18—C19—C20 | 118.0 (3) |
C10—N2—Pr | 119.4 (2) | C18—C19—H19 | 121.0 |
C6—N2—Pr | 122.6 (2) | C20—C19—H19 | 121.0 |
O33—N3—O32 | 121.2 (3) | N7—C20—C19 | 123.6 (3) |
O33—N3—O31 | 122.6 (3) | N7—C20—H20 | 118.2 |
O32—N3—O31 | 116.2 (3) | C19—C20—H20 | 118.2 |
O33—N3—Pr | 171.7 (3) | N8—C21—C22 | 123.1 (4) |
O32—N3—Pr | 57.17 (16) | N8—C21—H21A | 118.4 |
O31—N3—Pr | 59.77 (17) | C22—C21—H21A | 118.4 |
O43—N4—O42 | 120.9 (3) | C23—C22—C21 | 118.5 (4) |
O43—N4—O41 | 122.5 (3) | C23—C22—H22A | 120.7 |
O42—N4—O41 | 116.6 (3) | C21—C22—H22A | 120.7 |
O43—N4—Pr | 172.2 (3) | C22—C23—C24 | 118.8 (4) |
O42—N4—Pr | 56.97 (16) | C22—C23—H23 | 120.6 |
O41—N4—Pr | 59.87 (16) | C24—C23—H23 | 120.6 |
O53—N5—O52 | 121.8 (3) | C25—C24—C23 | 119.3 (4) |
O53—N5—O51 | 121.3 (3) | C25—C24—H24 | 120.3 |
O52—N5—O51 | 116.9 (3) | C23—C24—H24 | 120.3 |
O53—N5—Pr | 177.5 (3) | N8—C25—C24 | 121.1 (3) |
O52—N5—Pr | 58.77 (16) | N8—C25—C25i | 116.4 (4) |
O51—N5—Pr | 58.22 (16) | C24—C25—C25i | 122.4 (4) |
Symmetry code: (i) −x+2, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H11···O41ii | 0.85 (2) | 2.00 (3) | 2.797 (4) | 156 (4) |
O1W—H12···N6 | 0.85 (4) | 1.88 (2) | 2.707 (4) | 166 (5) |
O2W—H21···N8 | 0.86 (2) | 1.90 (2) | 2.751 (4) | 170 (4) |
O2W—H22···N7iii | 0.84 (3) | 2.01 (3) | 2.791 (4) | 157 (4) |
Symmetry codes: (ii) −x+2, −y+1, −z; (iii) x, y−1, z. |