Retracted: catena-Poly[hexa­kis(μ₂-anilino­acetamide)­bis­(1,10-phenanthroline)­dipraseodymium(III)]

The title compound, [Pr₂(C₈H₉N₂O)₆C₁₂H₈N₂)₂]_n, is a polymeric complex based on a binuclear unit with an inversion centre mid-way between the two Pr^III ions, which are bridged by two tridentate, two bidentate and four monodentate (within the binuclear unit) acetamide groups. Each Pr atom is nine-coordinated by two 1,10-phenanthroline N atoms and four O and three N atoms of anilinoacetamide ligands. In the crystal structure, C—H...O, C—H...N, N—H...N and N—H...O hydrogen bonds result in the formation of a supra­molecular network structure; an N—H...O hydrogen bond is also present within one ligand.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.012 Å
• R factor = 0.047
• wR factor = 0.138
• Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         N9
PLAT331_ALERT_2_B Small Average Phenyl C-C Dist.   C15    -C20           1.36 Ang.

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.79 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.76 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C6
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C23
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C33
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C31    -C36           1.37 Ang.
PLAT335_ALERT_2_C Large Benzene C-C Range .......  C4     -C6            0.18 Ang.
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         12
PLAT414_ALERT_2_C Short Intra D-H..H-X       H1     ..  H7A     ..       1.90 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor       N3     -   H3A    ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N8     -   H8     ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N9     -   H9     ...          ?
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      72.00 A   3 

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Pr1         (3)       6.21
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          6

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

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

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S1. Comment

The crystal structure of catena-Poly[hexakis(µ₂-anilinoacetamide)bis(1,10 -phenanthroline)disamarium(III)], (II), has previously been reported (Liu & Zhu, 2007). The crystal structure determination of the title compound, (I), has been carried out in order to elucidate the molecular conformation and to compare it with that of (II). We report herein the crystal structure of (I).

In the molecule of (I) (Fig. 1), the ligand bond lengths and angles (Table 1) are within normal ranges (Allen et al., 1987). It has an inversion centre midway between the two Pr^III ions, which are bridged by two tridentate, two bidentate and four mondentate acetamide groups. Each Pr atom is nine-coordinated by two N atoms of 1,10-phenanthroline (phen) ligand and four O and three N atoms of anilinoacetamide ligands. The Pr—O and Pr—N bonds are in the range of [2.520 (3)–2.573 (3) Å] and [2.414 (3)–2.863 (4) Å], respectively (Table 1), as in (II).

In the crystal structure, intermolecular C—H···O, C—H···N, N—H···N and N—H···O hydrogen bonds (Table 2, Fig. 2) result in the formation of a supramolecular network structure; intramolecular N—H···O hydrogen bond (Table 2) is also present, as in (II).

The both compounds, (I) and (II), are isostructural.

Related literature

For a related structure, see: Liu & Zhu (2007). For bond-length data, see: Allen et al. (1987).

S2. Experimental

Crystals of the title compound were synthesized using hydrothermal method in a 23 ml Teflon-lined Parr bomb. Praseodymium (III) nitrate hexahydrate (213.8 mg, 0.5 mmol), phen (198 mg, 1 mmol), anilinoacetamide (290.4 mg, 2 mmol) and distilled water (10 g) were placed into the bomb and sealed. The bomb was then heated under autogenous pressure up to 453 K over the course of 7 d and allowed to cool at room temperature for 24 h. Upon opening the bomb, a clear colorless solution was decanted from small colorless crystals. These crystals were washed with distilled water followed by ethanol, and allowed to air-dry at room temperature.

S3. Refinement

H5 and H8 (for NH) were located in difference syntheses and refined isotropically [N—H = 0.77 (2) and 0.81 (5) Å, U_iso(H) = 0.059 (18) and 0.07 (2) Ų]. The remaining H atoms were positioned geometrically, with N—H = 0.86 Å (for NH) and C—H = 0.93 and 0.97 Å, for aromatic and methylene H atoms and constrained to ride on their parent atoms, with U_iso(H) = 1.2U_eq(C,N).

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL (Siemens, 1996.

Figures

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level [symmetry code (A): 2 - x, -y, 2 - z]. H atoms have been omitted for clarity.
	Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines.

catena-Poly[hexakis(µ₂-anilinoacetamide)bis(1,10- phenanthroline)dipraseodymium(III)]

Crystal data

[Pr2(C8H9N2O)6(C12H8N2)2]	F(000) = 1560
Mr = 768.63	Dx = 1.512 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8891 reflections
a = 19.9013 (11) Å	θ = 2.6–26.5°
b = 8.6081 (14) Å	µ = 1.49 mm^−1
c = 20.581 (2) Å	T = 273 K
β = 106.774 (2)°	Plate, colourless
V = 3375.8 (7) Å^3	0.33 × 0.12 × 0.08 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	7311 independent reflections
Radiation source: fine-focus sealed tube	4903 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
φ and ω scans	θmax = 27.2°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −25→25
Tmin = 0.640, Tmax = 0.891	k = −10→11
26534 measured reflections	l = −26→26

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ^2(Fo^2) + (0.0902P)^2 + 0.285P] where P = (Fo^2 + 2Fc^2)/3
7311 reflections	(Δ/σ)max = 0.001
411 parameters	Δρmax = 1.39 e Å^−3
6 restraints	Δρmin = −0.72 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	0.931196 (13)	0.19067 (3)	0.964285 (12)	0.03954 (11)
O1	0.84617 (16)	−0.0357 (4)	0.91891 (16)	0.0470 (8)
O2	1.06673 (18)	−0.0827 (4)	0.92134 (16)	0.0521 (8)
O3	1.0070 (2)	0.6127 (4)	1.09077 (16)	0.0592 (10)
N1	0.7967 (2)	0.2336 (5)	0.9666 (2)	0.0496 (10)
N2	0.8344 (2)	0.3064 (4)	0.8549 (2)	0.0498 (10)
N3	0.97080 (18)	0.0613 (4)	0.87540 (16)	0.0343 (8)
H3A	0.9396	0.0556	0.8366	0.041*
N4	0.94712 (18)	−0.1394 (5)	0.97706 (17)	0.0364 (8)
H4	0.9440	−0.0483	0.9931	0.044*
N5	0.9401 (2)	0.4226 (4)	1.03380 (17)	0.0347 (8)
H5	0.932 (3)	0.335 (3)	1.035 (3)	0.059 (18)*
N7	1.1181 (2)	−0.0162 (5)	0.8217 (2)	0.0529 (11)
H7A	1.1395	−0.0737	0.8555	0.063*
N8	0.9877 (2)	0.5260 (5)	1.20638 (18)	0.0476 (10)
H8	0.962 (3)	0.600 (4)	1.2049 (19)	0.07 (2)*
N9	0.7855 (2)	−0.3271 (4)	0.8983 (2)	0.0489 (10)
H9	0.7624	−0.3420	0.8565	0.059*
C1	0.7787 (3)	0.1912 (7)	1.0202 (3)	0.0660 (16)
H1	0.8137	0.1683	1.0600	0.079*
C2	0.7092 (4)	0.1793 (9)	1.0196 (4)	0.086 (2)
H2	0.6977	0.1508	1.0587	0.104*
C3	0.6582 (4)	0.2099 (9)	0.9612 (5)	0.092 (2)
H3	0.6113	0.1976	0.9598	0.111*
C4	0.6746 (3)	0.2579 (10)	0.9053 (4)	0.0784 (19)
C5	0.7462 (3)	0.2669 (6)	0.9094 (3)	0.0544 (13)
C6	0.6218 (4)	0.2942 (11)	0.8397 (5)	0.115 (4)
H6	0.5743	0.2828	0.8354	0.138*
C7	0.6417 (4)	0.3421 (11)	0.7878 (4)	0.103 (3)
H7	0.6078	0.3697	0.7479	0.124*
C8	0.7134 (3)	0.3530 (8)	0.7911 (3)	0.0716 (18)
C9	0.7661 (3)	0.3092 (6)	0.8505 (3)	0.0551 (14)
C10	0.7358 (5)	0.4047 (9)	0.7374 (3)	0.090 (2)
H10	0.7033	0.4409	0.6982	0.109*
C11	0.8044 (5)	0.4030 (8)	0.7416 (3)	0.085 (2)
H11	0.8196	0.4369	0.7053	0.102*
C12	0.8526 (3)	0.3500 (7)	0.8007 (3)	0.0665 (16)
H12	0.8997	0.3450	0.8021	0.080*
C13	1.0285 (3)	0.0024 (6)	0.8772 (2)	0.0466 (11)
C14	1.0523 (3)	0.0517 (7)	0.8173 (3)	0.0567 (13)
H14A	1.0181	0.0192	0.7756	0.068*
H14B	1.0561	0.1640	0.8167	0.068*
C15	1.1460 (3)	0.0141 (7)	0.7694 (3)	0.0651 (15)
C16	1.2074 (3)	−0.0556 (9)	0.7760 (3)	0.0800 (19)
H16	1.2279	−0.1170	0.8137	0.096*
C17	1.2398 (4)	−0.0356 (10)	0.7265 (5)	0.096 (2)
H17	1.2831	−0.0820	0.7307	0.115*
C18	1.2086 (5)	0.0530 (10)	0.6708 (5)	0.111 (3)
H18	1.2303	0.0635	0.6367	0.134*
C19	1.1480 (5)	0.1242 (12)	0.6644 (4)	0.112 (3)
H19	1.1276	0.1854	0.6266	0.135*
C20	1.1149 (4)	0.1055 (9)	0.7159 (4)	0.086 (2)
H20	1.0726	0.1550	0.7130	0.103*
C21	0.8838 (3)	−0.1525 (6)	0.9388 (2)	0.0469 (12)
C22	0.8579 (3)	−0.3147 (6)	0.9198 (3)	0.0579 (14)
H22A	0.8764	−0.3512	0.8838	0.069*
H22B	0.8760	−0.3819	0.9587	0.069*
C23	0.7543 (7)	−0.3146 (10)	0.9466 (7)	0.1284 (17)
C24	0.7844 (7)	−0.2801 (10)	1.0107 (7)	0.1284 (17)
H24	0.8325	−0.2621	1.0264	0.154*
C25	0.7416 (6)	−0.2712 (11)	1.0554 (6)	0.1284 (17)
H25	0.7613	−0.2496	1.1012	0.154*
C26	0.6745 (6)	−0.2940 (10)	1.0307 (7)	0.1284 (17)
H26	0.6473	−0.2832	1.0603	0.154*
C27	0.6385 (6)	−0.3346 (10)	0.9613 (6)	0.1284 (17)
H27	0.5906	−0.3550	0.9462	0.154*
C28	0.6799 (6)	−0.3403 (11)	0.9207 (6)	0.1284 (17)
H28	0.6603	−0.3613	0.8748	0.154*
C29	0.9693 (3)	0.4994 (6)	1.0864 (2)	0.0463 (11)
C30	0.9488 (3)	0.4459 (7)	1.1474 (2)	0.0584 (14)
H30A	0.8991	0.4642	1.1402	0.070*
H30B	0.9573	0.3352	1.1536	0.070*
C31	0.9742 (3)	0.4889 (7)	1.2656 (2)	0.0579 (14)
C32	0.9279 (3)	0.3789 (9)	1.2721 (3)	0.0739 (18)
H32	0.9020	0.3237	1.2343	0.089*
C33	0.9195 (5)	0.3498 (12)	1.3343 (4)	0.109 (3)
H33	0.8890	0.2722	1.3395	0.131*
C34	0.9567 (5)	0.4366 (11)	1.3902 (3)	0.105 (3)
H34	0.9487	0.4217	1.4321	0.126*
C35	1.0043 (4)	0.5418 (9)	1.3836 (3)	0.091 (2)
H35	1.0304	0.5962	1.4215	0.109*
C36	1.0145 (3)	0.5696 (8)	1.3221 (3)	0.0743 (17)
H36	1.0478	0.6414	1.3179	0.089*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pr1	0.04542 (17)	0.03514 (17)	0.03339 (15)	−0.00150 (11)	0.00395 (10)	0.00062 (10)
O1	0.0468 (18)	0.0380 (19)	0.0487 (19)	−0.0002 (15)	0.0018 (14)	−0.0035 (14)
O2	0.063 (2)	0.051 (2)	0.0435 (19)	0.0085 (17)	0.0172 (16)	0.0114 (16)
O3	0.085 (3)	0.055 (2)	0.0387 (19)	−0.026 (2)	0.0200 (18)	−0.0049 (16)
N1	0.047 (2)	0.046 (2)	0.049 (2)	0.0037 (19)	0.0035 (19)	−0.0084 (19)
N2	0.060 (3)	0.045 (3)	0.036 (2)	0.0023 (19)	0.0004 (18)	0.0006 (17)
N3	0.0397 (19)	0.038 (2)	0.0239 (16)	0.0050 (17)	0.0073 (14)	0.0010 (15)
N4	0.0362 (19)	0.0320 (19)	0.0346 (19)	−0.0018 (15)	0.0000 (15)	0.0039 (15)
N5	0.054 (2)	0.0190 (19)	0.0296 (18)	−0.0064 (17)	0.0097 (15)	−0.0053 (14)
N7	0.052 (2)	0.070 (3)	0.043 (2)	0.017 (2)	0.0232 (19)	0.022 (2)
N8	0.068 (3)	0.047 (3)	0.030 (2)	−0.021 (2)	0.0169 (18)	−0.0050 (17)
N9	0.045 (2)	0.037 (2)	0.054 (3)	−0.0137 (18)	−0.0015 (19)	−0.0065 (18)
C1	0.059 (3)	0.080 (5)	0.059 (4)	0.008 (3)	0.018 (3)	0.000 (3)
C2	0.058 (4)	0.121 (7)	0.085 (5)	0.007 (4)	0.028 (4)	−0.010 (4)
C3	0.051 (4)	0.106 (7)	0.118 (7)	−0.004 (4)	0.020 (4)	−0.015 (5)
C4	0.055 (4)	0.094 (5)	0.072 (4)	0.006 (3)	−0.003 (3)	−0.017 (4)
C5	0.054 (3)	0.041 (3)	0.060 (3)	0.007 (2)	0.003 (2)	−0.008 (2)
C6	0.056 (4)	0.157 (10)	0.105 (7)	0.017 (5)	−0.020 (4)	−0.033 (6)
C7	0.079 (5)	0.119 (7)	0.080 (5)	0.038 (5)	−0.028 (4)	−0.018 (5)
C8	0.075 (4)	0.069 (4)	0.048 (3)	0.019 (3)	−0.017 (3)	−0.012 (3)
C9	0.063 (3)	0.037 (3)	0.051 (3)	0.005 (2)	−0.006 (2)	−0.005 (2)
C10	0.120 (6)	0.074 (5)	0.049 (4)	0.017 (4)	−0.021 (4)	0.001 (3)
C11	0.123 (6)	0.082 (5)	0.035 (3)	−0.003 (4)	0.001 (3)	0.013 (3)
C12	0.082 (4)	0.056 (4)	0.052 (3)	0.000 (3)	0.005 (3)	0.009 (3)
C13	0.062 (3)	0.039 (3)	0.037 (2)	−0.012 (2)	0.010 (2)	−0.003 (2)
C14	0.065 (3)	0.058 (3)	0.049 (3)	0.005 (3)	0.019 (2)	0.010 (2)
C15	0.070 (4)	0.074 (4)	0.059 (3)	−0.009 (3)	0.031 (3)	0.002 (3)
C16	0.079 (4)	0.099 (5)	0.073 (4)	0.005 (4)	0.040 (4)	−0.002 (4)
C17	0.092 (5)	0.098 (6)	0.115 (6)	−0.003 (5)	0.058 (5)	−0.006 (5)
C18	0.149 (8)	0.086 (6)	0.141 (8)	−0.015 (6)	0.108 (7)	−0.001 (6)
C19	0.153 (8)	0.118 (7)	0.093 (6)	0.022 (7)	0.077 (6)	0.035 (5)
C20	0.100 (5)	0.098 (5)	0.078 (4)	0.003 (4)	0.053 (4)	0.022 (4)
C21	0.048 (3)	0.055 (3)	0.033 (2)	−0.003 (2)	0.004 (2)	−0.005 (2)
C22	0.064 (3)	0.050 (3)	0.055 (3)	0.004 (3)	0.009 (3)	−0.005 (2)
C23	0.139 (4)	0.097 (3)	0.174 (5)	0.017 (3)	0.084 (4)	0.032 (3)
C24	0.139 (4)	0.097 (3)	0.174 (5)	0.017 (3)	0.084 (4)	0.032 (3)
C25	0.139 (4)	0.097 (3)	0.174 (5)	0.017 (3)	0.084 (4)	0.032 (3)
C26	0.139 (4)	0.097 (3)	0.174 (5)	0.017 (3)	0.084 (4)	0.032 (3)
C27	0.139 (4)	0.097 (3)	0.174 (5)	0.017 (3)	0.084 (4)	0.032 (3)
C28	0.139 (4)	0.097 (3)	0.174 (5)	0.017 (3)	0.084 (4)	0.032 (3)
C29	0.058 (3)	0.035 (3)	0.045 (3)	−0.002 (2)	0.014 (2)	0.005 (2)
C30	0.077 (4)	0.057 (3)	0.043 (3)	−0.022 (3)	0.018 (2)	−0.006 (2)
C31	0.076 (4)	0.059 (3)	0.038 (3)	−0.003 (3)	0.015 (2)	0.004 (2)
C32	0.076 (4)	0.096 (5)	0.052 (3)	−0.034 (4)	0.022 (3)	−0.006 (3)
C33	0.124 (7)	0.145 (8)	0.070 (5)	−0.046 (6)	0.046 (5)	0.003 (5)
C34	0.124 (6)	0.148 (8)	0.051 (4)	−0.030 (6)	0.038 (4)	0.007 (5)
C35	0.118 (6)	0.105 (6)	0.045 (3)	−0.018 (5)	0.014 (3)	−0.008 (4)
C36	0.086 (4)	0.082 (5)	0.051 (3)	−0.018 (4)	0.013 (3)	−0.013 (3)

Geometric parameters (Å, º)

Pr1—O1	2.573 (3)	C8—C9	1.413 (7)
Pr1—O2^i	2.520 (3)	C10—C11	1.344 (10)
Pr1—O3^ii	2.543 (3)	C10—H10	0.9300
Pr1—N1	2.715 (4)	C11—C12	1.389 (8)
Pr1—N2	2.696 (4)	C11—H11	0.9300
Pr1—N3	2.458 (3)	C12—H12	0.9300
Pr1—N4	2.863 (4)	C13—C14	1.502 (7)
Pr1—N4^i	2.414 (3)	C14—H14A	0.9700
Pr1—N5	2.433 (4)	C14—H14B	0.9700
O1—C21	1.250 (6)	C15—C16	1.334 (9)
O2—C13	1.243 (6)	C15—C20	1.350 (9)
O2—Pr1^i	2.520 (3)	C16—C17	1.363 (10)
O3—C29	1.217 (6)	C16—H16	0.9300
O3—Pr1^ii	2.543 (3)	C17—C18	1.369 (12)
N1—C1	1.306 (7)	C17—H17	0.9300
N1—C5	1.340 (7)	C18—C19	1.325 (11)
N2—C12	1.323 (7)	C18—H18	0.9300
N2—C9	1.336 (7)	C19—C20	1.409 (9)
N3—C13	1.246 (6)	C19—H19	0.9300
N3—H3A	0.8600	C20—H20	0.9300
N4—C21	1.284 (6)	C21—C22	1.500 (7)
N4—Pr1^i	2.414 (3)	C22—H22A	0.9700
N4—H4	0.8600	C22—H22B	0.9700
N5—C29	1.258 (6)	C23—C24	1.316 (16)
N5—H5	0.77 (2)	C23—C28	1.438 (16)
N7—C15	1.372 (7)	C24—C25	1.424 (13)
N7—C14	1.413 (6)	C24—H24	0.9300
N7—H7A	0.8600	C25—C26	1.300 (15)
N8—C31	1.360 (6)	C25—H25	0.9300
N8—C30	1.416 (6)	C26—C27	1.444 (16)
N8—H8	0.81 (5)	C26—H26	0.9300
N9—C23	1.319 (12)	C27—C28	1.332 (12)
N9—C22	1.384 (7)	C27—H27	0.9300
N9—H9	0.8600	C28—H28	0.9300
C1—C2	1.384 (9)	C29—C30	1.500 (7)
C1—H1	0.9300	C30—H30A	0.9700
C2—C3	1.357 (11)	C30—H30B	0.9700
C2—H2	0.9300	C31—C32	1.354 (8)
C3—C4	1.348 (11)	C31—C36	1.393 (8)
C3—H3	0.9300	C32—C33	1.363 (9)
C4—C5	1.407 (8)	C32—H32	0.9300
C4—C6	1.486 (11)	C33—C34	1.391 (11)
C5—C9	1.428 (8)	C33—H33	0.9300
C6—C7	1.306 (13)	C34—C35	1.345 (10)
C6—H6	0.9300	C34—H34	0.9300
C7—C8	1.413 (11)	C35—C36	1.359 (9)
C7—H7	0.9300	C35—H35	0.9300
C8—C10	1.379 (10)	C36—H36	0.9300
O1—Pr1—N1	63.97 (12)	N1—C5—C9	118.6 (5)
O1—Pr1—N2	74.94 (11)	C4—C5—C9	119.3 (5)
O1—Pr1—N3	72.85 (11)	C7—C6—C4	120.6 (8)
O1—Pr1—N4	47.58 (10)	C7—C6—H6	119.7
O1—Pr1—N5	139.78 (12)	C4—C6—H6	119.7
N1—Pr1—N2	59.62 (14)	C6—C7—C8	121.4 (7)
N1—Pr1—N3	127.16 (12)	C6—C7—H7	119.3
N1—Pr1—N4	102.53 (12)	C8—C7—H7	119.3
N1—Pr1—N5	77.46 (13)	C10—C8—C9	116.6 (6)
N2—Pr1—N3	81.43 (12)	C10—C8—C7	122.6 (7)
N2—Pr1—N4	118.48 (11)	C9—C8—C7	120.8 (7)
N2—Pr1—N5	95.81 (12)	N2—C9—C8	123.4 (6)
N3—Pr1—N4	64.39 (11)	N2—C9—C5	117.6 (5)
N3—Pr1—N5	145.60 (12)	C8—C9—C5	118.9 (6)
N4—Pr1—N5	140.65 (11)	C11—C10—C8	120.2 (6)
N4^i—Pr1—N5	87.92 (13)	C11—C10—H10	119.9
N4^i—Pr1—N3	78.38 (12)	C8—C10—H10	119.9
N4^i—Pr1—O2^i	73.85 (11)	C10—C11—C12	119.5 (6)
N5—Pr1—O2^i	76.97 (12)	C10—C11—H11	120.3
N3—Pr1—O2^i	127.29 (12)	C12—C11—H11	120.3
N4^i—Pr1—O2^i	73.85 (11)	N2—C12—C11	122.9 (7)
N5—Pr1—O2^i	76.97 (12)	N2—C12—H12	118.5
N3—Pr1—O2^i	127.29 (12)	C11—C12—H12	118.5
O2^i—Pr1—O2^i	0.0 (2)	O2—C13—N3	128.7 (5)
N4^i—Pr1—O2^i	73.85 (11)	O2—C13—C14	119.7 (5)
N5—Pr1—O2^i	76.97 (12)	N3—C13—C14	111.5 (4)
N3—Pr1—O2^i	127.29 (12)	N7—C14—C13	109.6 (4)
O2^i—Pr1—O2^i	0.0 (2)	N7—C14—H14A	109.7
O2^i—Pr1—O2^i	0.0 (2)	C13—C14—H14A	109.7
N4^i—Pr1—O3^ii	78.47 (13)	N7—C14—H14B	109.7
N5—Pr1—O3^ii	75.71 (12)	C13—C14—H14B	109.7
N3—Pr1—O3^ii	70.72 (11)	H14A—C14—H14B	108.2
O2^i—Pr1—O3^ii	141.45 (11)	C16—C15—C20	122.4 (6)
O2^i—Pr1—O3^ii	141.45 (11)	C16—C15—N7	113.7 (6)
O2^i—Pr1—O3^ii	141.45 (11)	C20—C15—N7	123.9 (6)
N4^i—Pr1—O1	120.18 (12)	C15—C16—C17	119.0 (7)
O2^i—Pr1—O1	83.77 (11)	C15—C16—H16	120.5
O2^i—Pr1—O1	83.77 (11)	C17—C16—H16	120.5
O2^i—Pr1—O1	83.77 (11)	C16—C17—C18	119.9 (8)
O3^ii—Pr1—O1	133.98 (11)	C16—C17—H17	120.1
N4^i—Pr1—N2	148.97 (13)	C18—C17—H17	120.1
O2^i—Pr1—N2	137.01 (13)	C19—C18—C17	121.4 (7)
O2^i—Pr1—N2	137.01 (13)	C19—C18—H18	119.3
O2^i—Pr1—N2	137.01 (13)	C17—C18—H18	119.3
O3^ii—Pr1—N2	72.71 (13)	C18—C19—C20	118.8 (8)
N4^i—Pr1—N1	150.16 (12)	C18—C19—H19	120.6
O2^i—Pr1—N1	77.54 (12)	C20—C19—H19	120.6
O2^i—Pr1—N1	77.54 (12)	C15—C20—C19	118.4 (7)
O2^i—Pr1—N1	77.54 (12)	C15—C20—H20	120.8
O3^ii—Pr1—N1	121.54 (14)	C19—C20—H20	120.8
N4^i—Pr1—N4	72.79 (13)	O1—C21—N4	121.3 (5)
O2^i—Pr1—N4	64.96 (11)	O1—C21—C22	122.4 (4)
O2^i—Pr1—N4	64.96 (11)	N4—C21—C22	116.4 (5)
O2^i—Pr1—N4	64.96 (11)	N9—C22—C21	113.8 (4)
O3^ii—Pr1—N4	130.29 (11)	N9—C22—H22A	108.8
N4^i—Pr1—H5	87.3 (18)	C21—C22—H22A	108.8
N3—Pr1—H5	158.2 (15)	N9—C22—H22B	108.8
O2^i—Pr1—H5	62.2 (12)	C21—C22—H22B	108.8
O2^i—Pr1—H5	62.2 (12)	H22A—C22—H22B	107.7
O2^i—Pr1—H5	62.2 (12)	C24—C23—N9	126.5 (12)
O3^ii—Pr1—H5	90.5 (12)	C24—C23—C28	122.0 (11)
O1—Pr1—H5	128.9 (14)	N9—C23—C28	111.5 (12)
N2—Pr1—H5	104.0 (17)	C23—C24—C25	118.3 (13)
N1—Pr1—H5	71.8 (17)	C23—C24—H24	120.9
N4—Pr1—H5	126.8 (13)	C25—C24—H24	120.9
C21—O1—Pr1	102.8 (3)	C26—C25—C24	118.6 (13)
C13—O2—Pr1^i	138.0 (3)	C26—C25—H25	120.7
C29—O3—Pr1^ii	150.1 (3)	C24—C25—H25	120.7
C1—N1—C5	118.9 (5)	C25—C26—C27	125.7 (11)
C1—N1—Pr1	119.2 (4)	C25—C26—H26	117.2
C5—N1—Pr1	120.5 (4)	C27—C26—H26	117.2
C12—N2—C9	117.2 (5)	C28—C27—C26	114.1 (12)
C12—N2—Pr1	120.4 (4)	C28—C27—H27	122.9
C9—N2—Pr1	122.1 (3)	C26—C27—H27	122.9
C13—N3—Pr1	130.8 (3)	C27—C28—C23	121.2 (13)
C13—N3—H3A	114.6	C27—C28—H28	119.4
Pr1—N3—H3A	114.6	C23—C28—H28	119.4
C21—N4—Pr1^i	162.9 (4)	O3—C29—N5	127.3 (5)
C21—N4—Pr1	88.2 (3)	O3—C29—C30	119.6 (4)
Pr1^i—N4—Pr1	107.21 (13)	N5—C29—C30	112.9 (4)
C21—N4—H4	98.5	N8—C30—C29	110.8 (4)
Pr1^i—N4—H4	98.5	N8—C30—H30A	109.5
C29—N5—Pr1	150.9 (3)	C29—C30—H30A	109.5
C29—N5—H5	122 (5)	N8—C30—H30B	109.5
C15—N7—C14	116.7 (4)	C29—C30—H30B	109.5
C15—N7—H7A	121.7	H30A—C30—H30B	108.1
C14—N7—H7A	121.7	C32—C31—N8	124.7 (5)
C31—N8—C30	116.9 (4)	C32—C31—C36	120.7 (5)
C31—N8—H8	86.1 (17)	N8—C31—C36	114.6 (5)
C30—N8—H8	100 (4)	C32—C31—H8	124 (2)
C23—N9—C22	115.2 (8)	C36—C31—H8	107 (2)
C23—N9—H9	122.4	C31—C32—C33	119.5 (6)
C22—N9—H9	122.4	C31—C32—H32	120.3
N1—C1—C2	122.1 (6)	C33—C32—H32	120.3
N1—C1—H1	119.0	C32—C33—C34	119.9 (7)
C2—C1—H1	119.0	C32—C33—H33	120.1
C3—C2—C1	119.0 (7)	C34—C33—H33	120.1
C3—C2—H2	120.5	C35—C34—C33	120.1 (6)
C1—C2—H2	120.5	C35—C34—H34	120.0
C4—C3—C2	120.7 (7)	C33—C34—H34	120.0
C4—C3—H3	119.6	C34—C35—C36	120.7 (7)
C2—C3—H3	119.6	C34—C35—H35	119.7
C3—C4—C5	117.2 (6)	C36—C35—H35	119.7
C3—C4—C6	124.0 (7)	C35—C36—C31	119.0 (6)
C5—C4—C6	118.7 (7)	C35—C36—H36	120.5
N1—C5—C4	122.1 (6)	C31—C36—H36	120.5

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22B···N5^iii	0.97	2.39	3.329 (7)	163
C12—H12···N8^ii	0.93	2.55	3.395 (8)	151
C12—H12···O3^ii	0.93	2.47	3.050 (7)	121
C10—H10···O1^iv	0.93	2.33	3.201 (7)	155
C1—H1···O2^i	0.93	2.41	3.105 (7)	131
N7—H7A···O2	0.86	2.25	2.605 (5)	105
N5—H5···O2^i	0.77 (2)	2.35 (3)	3.083 (5)	159 (6)
N4—H4···N4^i	0.86	2.63	3.152 (8)	120
N4—H4···O2^i	0.86	2.15	2.905 (5)	146

Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+2, −y+1, −z+2; (iii) x, y−1, z; (iv) −x+3/2, y+1/2, −z+3/2.