(Acetyl­acetonato)aqua­(2,2′,2′′-ter­pyri­dine)chromium(III) bis­(perchlorate) dihydrate hexa­methyl­phos­phor­amide solvate

The title compound, [Cr(C₅H₈O₂)(C₁₅H₁₁N₃)(H₂O)](ClO₄)₂·2H₂O·C₆H₁₈N₃OP, adopts a distorted octa­hedral configuration about the Cr^III atom, mainly due to the rigidity of the terpyridyl ligand. The N—Cr—N bite angles are significantly distorted from 90° at 78.3 (1) and 78.6 (1)°. The Cr—N bond distances vary between 1.998 (1) and 2.068 (1) Å. The crystal packing is controlled by hydrogen bonding and π-stacking, with an interplanar separation of 3.263 (2) Å.

Key indicators

• Single-crystal X-ray study
• T = 101 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.030
• wR factor = 0.080
• Data-to-parameter ratio = 18.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cr1    -   O2      ..       5.62 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cr1    -   N3      ..       5.51 su
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl2
PLAT432_ALERT_2_C Short Inter X...Y Contact  O12    ..  C25     ..       3.00 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1A    ..  O13     ..       2.77 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1A    ..  O13     ..       2.77 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 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
   3 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

The title compound, [Cr(acac)(H₂O)(terpy)]·2(ClO₄)·2(H₂O)·(PON₃C₆H₁₈), (terpy = 2,2',2''-terpyridine and acac = acetyl acetonoate), (I), contains a chromium(III) atom which is octahedrally surrounded by three N atoms (N1, N2 and N3) of the terpy ligand, two O atoms from the acac ligand and another O atom from the coordinated H₂O molecule (Figure 1). The Cr-atom in (I) adopts a distorted octahedral geometry where the mean intraligand N—Cr—N bond angle is 78.4 (1)°, similar to bond angles in mer-[CrCl₃(terpy)] (Cloete et al., 2007). The rigidity of the terpyridyl group necessatates the above mentioned bite angles to be much smaller than 90°. The O1—Cr—O2 bond angle is 91.1 (1)° which is equal to the average intramolecular O—Cr—O bond angle reported in [Cr(acac)₃ (Morosin, 1965)].

The mean Cr—N(peripheral) distance of 2.062 (1) Å is slightly longer than the Cr—N(central) bond distance (1.998 (1) Å). This difference of approximately 0.08 Å has also been observed in mer-[Cr(terpy)₂]³⁺ (Wickramasinghe et al., 1982) and in the metallo-mono(terpy) complexes mer-[CrCl₃(terpy)] (Cloete et al., 2007), [mer-[GaCl₂(terpy)] (0.078 Å) (Beran et al., 1970), mer-[ZnCl₂(terpy)] (0.12 Å) (Einstein et al., 1966) and mer-[(CH₃)₂SnCl(terpy)]⁺ (0.08 Å) (Einstein et al., 1968). The C—C bond distances for the acac ligand range between 1.384 (2) and 1.496 Å. These bond lengths are consistent with the partial double bond character of the acetylacetonate ligand in which the electrons are delocalized in the chelate ring.

The other bonds in complex (I) fall within the same range as the corresponding complexes (Beran et al., 1970; Cloete et al., 2007; Einstein et al., 1966; Einstein et al., 1968; Liu & Verkade, 1998; Shiren & Tanaka, 2002 and Visser et al., 2005).

The [Cr(acac)(H₂O)(terpy)] cations are packed diagonally across the ac plane with the perchlorate anions, hexamethylphosphoramide and water molecules filling the spaces in between (Fig. 2). The molecules within the structure are linked by an extensive network of intermolecular hydrogen bonds and non-conventinal H-bonds of the types C—H···O and C—H···N. The crystal packing also seems to be influenced by π-π stacking interactions between the terpy moieties (Fig. 2) with an interplanar separation of 3.263 (2) Å.

Related literature

For similar complexes, see: Beran et al. (1970); Cloete et al. (2007); Einstein & Penfold (1966, 1968); Liu & Verkade (1998); Morosin (1965); Shiren & Tanaka (2002); Visser et al. (2005); Wickramasinghe et al. (1982). For the synthesis of the starting complex mer-[CrCl₃(terpy)], see: Cloete et al. (2007).

S2. Experimental

[Cr(terpy)Cl₃] (Cloete et al., 2007) (1.5 g, 3.2 mmole) was dissolved in methanol (300 ml). AgClO₄ (0.662 g, 3.2 mmole) was added to the methanol solution and stirred at room temperature for 12 h. The solution was filtered. NaOH (0.13 g, 3.2 mmole) and acetylacetone (3.3 ml 3.2 mmole) was added to the filtrate. Reaction mixture was stirred for another 12 h after which the solution was acidified with HClO₄ (5 ml, 60% v/v) and stirred for two hours. H₂O (100 ml) was added and the solution was left to slowly evaporate at room temperature. Single red cystals were obtained after 1 day which were suitable for X-ray crystallography. Yield: 0.199 g (76.1%)

S3. Refinement

The aromatic, methylene and methyl (hexamethylphosphoramide molecule) hydrogen atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with U_iso(H) = 1.5U_eq(C) and 1.2U_eq(C), respectively. The hydrogen atoms on the methyl groups of the acac ligand were constrained to ride on their parent atoms and idealized as rotating CH₃ groups. Aqua H atoms were located in a difference Fourier map and then refined isotropically. The H atom on the C3 atom of the acac group was located in a difference Fourier map and then refined isotropically. The maximum and the minimum residual electron density are located 0.69 Å from N6 and 0.69 Å from Cr1, respectively, indicating no physical meaning.

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

	Fig. 1. : View of (I) with 50% probability displacement ellipsoids; H-atoms were omitted for clarity.
	Fig. 2. : View of (I) along the b axis, illustrating selected H-bonds and π stacking. i) (-x, 2 - y, -z) ii) (x, y, -1 + z) iii) (3/2 - x, 1/2 + y, 1/2 - z)

(Acetylacetonato)aqua(2,2',2''-terpyridine)chromium(III) bis(perchlorate) dihydrate hexamethylphosphoramide solvate

Crystal data

[Cr(C5H7O2)(C15H11N3)(H2O)](ClO4)2·2(H2O)·C6H18N3OP	F(000) = 1700
Mr = 816.53	Dx = 1.537 Mg m^−3 Dm = 1.54 Mg m^−3 Dm measured by not measured
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9416 reflections
a = 13.2524 (4) Å	θ = 2.5–28.3°
b = 13.5607 (4) Å	µ = 0.59 mm^−1
c = 19.7271 (6) Å	T = 101 K
β = 95.588 (1)°	Cuboid, red
V = 3528.35 (18) Å^3	0.26 × 0.24 × 0.19 mm
Z = 4

Data collection

Bruker X8 APEXII 4K Kappa CCD diffractometer	7534 reflections with I > 2σ(I)
ω and ϕ scans	Rint = 0.032
Absorption correction: multi-scan (SADABS; Bruker, 2004)	θmax = 28.3°, θmin = 1.8°
Tmin = 0.850, Tmax = 0.899	h = −17→17
61605 measured reflections	k = −18→18
8750 independent reflections	l = −24→26

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.030	w = 1/[σ^2(Fo^2) + (0.0529P)^2 + 4.3676P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.08	(Δ/σ)max = 0.001
S = 1.02	Δρmax = 0.4 e Å^−3
8750 reflections	Δρmin = −0.42 e Å^−3
477 parameters

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cr1	0.126363 (16)	0.768594 (16)	0.120659 (11)	0.01100 (6)
Cl1	0.19255 (3)	0.33434 (3)	0.091107 (18)	0.01726 (8)
Cl2	0.69017 (3)	0.49729 (3)	0.254242 (19)	0.02045 (9)
O1	−0.02022 (8)	0.76518 (7)	0.11518 (5)	0.0145 (2)
O2	0.13586 (8)	0.67037 (8)	0.19157 (5)	0.0160 (2)
N2	0.12138 (9)	0.87546 (9)	0.05072 (6)	0.0127 (2)
N3	0.12156 (9)	0.68837 (9)	0.03127 (6)	0.0137 (2)
N1	0.12924 (9)	0.89261 (9)	0.18065 (6)	0.0141 (2)
O6	0.24232 (9)	0.25598 (9)	0.13100 (6)	0.0260 (3)
P1	0.43832 (3)	0.77800 (3)	0.995845 (19)	0.01538 (8)
O12	0.34383 (8)	0.82187 (9)	1.01873 (6)	0.0222 (2)
N4	0.42298 (10)	0.75554 (10)	0.91434 (7)	0.0199 (3)
N5	0.47021 (10)	0.66964 (10)	1.02906 (7)	0.0203 (3)
O13	0.39785 (10)	0.80887 (10)	0.23635 (7)	0.0252 (3)
O14	0.89534 (10)	0.29744 (12)	0.25721 (7)	0.0289 (3)
N6	0.53124 (10)	0.85556 (10)	1.01509 (7)	0.0206 (3)
C7	0.35895 (13)	0.81940 (15)	0.86919 (9)	0.0281 (4)
H7A	0.3191	0.8608	0.8957	0.042*
H7B	0.3148	0.7798	0.8388	0.042*
H7C	0.4007	0.8597	0.8433	0.042*
C8	0.39334 (13)	0.59136 (13)	1.02112 (10)	0.0288 (4)
H8A	0.3511	0.601	0.9793	0.043*
H8B	0.3524	0.5935	1.0587	0.043*
H8C	0.4262	0.5284	1.0202	0.043*
C9	0.53796 (14)	0.66036 (14)	1.09146 (9)	0.0299 (4)
H9A	0.5865	0.7131	1.0939	0.045*
H9B	0.5728	0.5983	1.0915	0.045*
H9C	0.4992	0.6635	1.1301	0.045*
C17	0.53491 (16)	0.91838 (14)	1.07527 (9)	0.0324 (4)
H17A	0.4708	0.9158	1.0941	0.049*
H17B	0.5489	0.9851	1.0628	0.049*
H17C	0.5874	0.8956	1.1086	0.049*
C6	0.48678 (14)	0.68963 (14)	0.87875 (9)	0.0298 (4)
H6A	0.5269	0.6497	0.9113	0.045*
H6B	0.5307	0.7278	0.853	0.045*
H6C	0.4448	0.6479	0.8485	0.045*
C10	0.62493 (13)	0.85386 (15)	0.98238 (10)	0.0298 (4)
H10A	0.6169	0.8114	0.9433	0.045*
H10B	0.679	0.8297	1.0139	0.045*
H10C	0.6407	0.9194	0.9683	0.045*
O3	0.27545 (8)	0.76660 (8)	0.12612 (6)	0.0162 (2)
H5A	0.3840 (19)	0.8279 (19)	0.2696 (14)	0.047 (8)*
H5B	0.465 (2)	0.8070 (18)	0.2371 (12)	0.045 (7)*
H4B	0.8704 (19)	0.244 (2)	0.2575 (13)	0.045 (7)*
H4A	0.852 (2)	0.342 (2)	0.2664 (16)	0.078 (10)*
H45	0.3038 (17)	0.7814 (16)	0.1576 (12)	0.030 (6)*
H46	0.3014 (19)	0.7886 (18)	0.0903 (14)	0.050 (7)*
C31	0.11945 (11)	0.74333 (11)	−0.02662 (7)	0.0144 (3)
O4	0.11986 (9)	0.29300 (9)	0.04007 (6)	0.0284 (3)
O5	0.26586 (9)	0.39128 (9)	0.05905 (6)	0.0263 (3)
C25	0.12033 (10)	0.85093 (11)	−0.01524 (7)	0.0145 (3)
C22	0.12551 (11)	1.04583 (11)	0.02463 (8)	0.0182 (3)
H22	0.128	1.1113	0.0387	0.022*
C34	0.11710 (12)	0.54218 (12)	−0.03595 (8)	0.0214 (3)
H34	0.1158	0.4737	−0.0382	0.026*
C13	0.12692 (13)	1.06842 (12)	0.25091 (9)	0.0252 (4)
H13	0.1256	1.1276	0.2747	0.03*
O7	0.14090 (9)	0.39758 (9)	0.13592 (6)	0.0250 (3)
C15	0.12453 (11)	0.97999 (11)	0.14630 (8)	0.0154 (3)
C24	0.12035 (11)	0.92365 (12)	−0.06455 (8)	0.0177 (3)
H24	0.1184	0.9073	−0.1104	0.021*
C14	0.12233 (12)	1.06858 (11)	0.18027 (9)	0.0212 (3)
H14	0.1178	1.1277	0.1563	0.025*
C12	0.13348 (13)	0.98032 (12)	0.28550 (9)	0.0233 (3)
H12	0.1375	0.9791	0.3328	0.028*
C2	0.06322 (11)	0.62566 (11)	0.21764 (7)	0.0153 (3)
C4	−0.07570 (11)	0.70747 (11)	0.14682 (7)	0.0148 (3)
C3	−0.03864 (11)	0.63886 (11)	0.19608 (8)	0.0175 (3)
H3	−0.0854	0.5995	0.2157	0.021*
C21	0.12382 (10)	0.96977 (11)	0.07163 (8)	0.0146 (3)
C5	−0.18745 (12)	0.71765 (12)	0.12873 (8)	0.0213 (3)
H5C	−0.2025	0.7109	0.0804	0.032*
H5D	−0.2093	0.7813	0.1428	0.032*
H5E	−0.2223	0.6672	0.1514	0.032*
C32	0.11698 (11)	0.69970 (12)	−0.08987 (8)	0.0193 (3)
H32	0.1161	0.7382	−0.1289	0.023*
C33	0.11581 (12)	0.59778 (13)	−0.09459 (8)	0.0228 (3)
H33	0.1142	0.5671	−0.1369	0.027*
O8	0.67088 (11)	0.59924 (9)	0.26969 (7)	0.0355 (3)
C35	0.12030 (11)	0.58980 (11)	0.02628 (8)	0.0173 (3)
H35	0.1216	0.5523	0.0658	0.021*
C11	0.13407 (11)	0.89343 (12)	0.24870 (8)	0.0183 (3)
H11	0.138	0.8337	0.272	0.022*
O9	0.69011 (12)	0.48494 (11)	0.18257 (7)	0.0400 (3)
O11	0.61525 (11)	0.43677 (10)	0.28030 (7)	0.0383 (3)
O10	0.78831 (11)	0.47091 (11)	0.28708 (9)	0.0482 (4)
C23	0.12333 (11)	1.02168 (12)	−0.04377 (8)	0.0196 (3)
H23	0.1239	1.0716	−0.0761	0.024*
C1	0.09592 (13)	0.55771 (12)	0.27532 (8)	0.0232 (3)
H1A	0.1417	0.5093	0.2604	0.035*
H1B	0.0376	0.5253	0.2903	0.035*
H1C	0.1294	0.5949	0.3123	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cr1	0.01239 (11)	0.00971 (11)	0.01106 (11)	0.00019 (8)	0.00199 (8)	0.00174 (8)
Cl1	0.01874 (17)	0.01400 (16)	0.01917 (18)	−0.00186 (13)	0.00244 (13)	0.00061 (13)
Cl2	0.02155 (18)	0.01963 (18)	0.01980 (18)	−0.00030 (14)	0.00005 (14)	0.00105 (14)
O1	0.0145 (5)	0.0144 (5)	0.0149 (5)	−0.0007 (4)	0.0027 (4)	0.0021 (4)
O2	0.0179 (5)	0.0144 (5)	0.0159 (5)	0.0002 (4)	0.0023 (4)	0.0037 (4)
N2	0.0106 (5)	0.0127 (6)	0.0150 (6)	0.0003 (4)	0.0024 (4)	0.0027 (5)
N3	0.0126 (6)	0.0140 (6)	0.0147 (6)	0.0000 (4)	0.0017 (4)	0.0011 (5)
N1	0.0134 (6)	0.0129 (6)	0.0161 (6)	0.0004 (4)	0.0027 (4)	0.0001 (5)
O6	0.0289 (6)	0.0195 (6)	0.0300 (6)	0.0038 (5)	0.0047 (5)	0.0084 (5)
P1	0.01319 (17)	0.01865 (19)	0.01444 (18)	0.00062 (14)	0.00207 (13)	0.00170 (14)
O12	0.0190 (5)	0.0292 (6)	0.0191 (6)	0.0052 (5)	0.0065 (4)	0.0047 (5)
N4	0.0168 (6)	0.0264 (7)	0.0165 (6)	0.0026 (5)	0.0008 (5)	−0.0011 (5)
N5	0.0177 (6)	0.0196 (7)	0.0229 (7)	−0.0013 (5)	−0.0013 (5)	0.0035 (5)
O13	0.0238 (7)	0.0298 (7)	0.0217 (6)	−0.0018 (5)	0.0006 (5)	−0.0059 (5)
O14	0.0271 (7)	0.0302 (7)	0.0295 (7)	−0.0027 (6)	0.0024 (5)	−0.0020 (6)
N6	0.0203 (6)	0.0215 (7)	0.0199 (6)	−0.0036 (5)	0.0015 (5)	−0.0006 (5)
C7	0.0242 (8)	0.0402 (10)	0.0193 (8)	0.0053 (7)	−0.0006 (6)	0.0048 (7)
C8	0.0249 (9)	0.0204 (8)	0.0404 (10)	−0.0033 (7)	0.0002 (7)	0.0049 (7)
C9	0.0309 (9)	0.0274 (9)	0.0294 (9)	0.0016 (7)	−0.0074 (7)	0.0079 (7)
C17	0.0436 (11)	0.0278 (9)	0.0245 (9)	−0.0035 (8)	−0.0041 (8)	−0.0047 (7)
C6	0.0297 (9)	0.0349 (10)	0.0249 (9)	0.0043 (8)	0.0036 (7)	−0.0109 (8)
C10	0.0177 (8)	0.0378 (10)	0.0339 (10)	−0.0062 (7)	0.0020 (7)	0.0026 (8)
O3	0.0148 (5)	0.0207 (6)	0.0132 (5)	0.0002 (4)	0.0017 (4)	0.0014 (4)
C31	0.0117 (6)	0.0169 (7)	0.0148 (7)	0.0009 (5)	0.0020 (5)	0.0021 (6)
O4	0.0258 (6)	0.0299 (7)	0.0285 (6)	−0.0049 (5)	−0.0022 (5)	−0.0083 (5)
O5	0.0258 (6)	0.0238 (6)	0.0302 (6)	−0.0049 (5)	0.0081 (5)	0.0067 (5)
C25	0.0098 (6)	0.0187 (7)	0.0153 (7)	0.0010 (5)	0.0023 (5)	0.0034 (6)
C22	0.0134 (7)	0.0134 (7)	0.0280 (8)	0.0000 (5)	0.0027 (6)	0.0052 (6)
C34	0.0225 (8)	0.0169 (7)	0.0246 (8)	0.0004 (6)	0.0015 (6)	−0.0055 (6)
C13	0.0270 (8)	0.0188 (8)	0.0299 (9)	−0.0021 (6)	0.0033 (7)	−0.0099 (7)
O7	0.0334 (7)	0.0190 (6)	0.0234 (6)	0.0038 (5)	0.0071 (5)	−0.0017 (5)
C15	0.0121 (6)	0.0135 (7)	0.0205 (7)	−0.0010 (5)	0.0020 (5)	0.0002 (6)
C24	0.0125 (7)	0.0246 (8)	0.0162 (7)	0.0019 (6)	0.0026 (5)	0.0062 (6)
C14	0.0215 (8)	0.0130 (7)	0.0293 (9)	−0.0015 (6)	0.0041 (6)	−0.0013 (6)
C12	0.0251 (8)	0.0254 (8)	0.0193 (8)	−0.0003 (7)	0.0023 (6)	−0.0055 (6)
C2	0.0234 (7)	0.0106 (7)	0.0126 (7)	−0.0005 (5)	0.0043 (5)	−0.0008 (5)
C4	0.0174 (7)	0.0143 (7)	0.0132 (7)	−0.0018 (5)	0.0037 (5)	−0.0031 (5)
C3	0.0205 (7)	0.0155 (7)	0.0173 (7)	−0.0042 (6)	0.0062 (6)	0.0021 (6)
C21	0.0106 (6)	0.0127 (7)	0.0207 (7)	−0.0004 (5)	0.0029 (5)	0.0026 (6)
C5	0.0160 (7)	0.0246 (8)	0.0235 (8)	−0.0020 (6)	0.0037 (6)	0.0015 (6)
C32	0.0176 (7)	0.0258 (8)	0.0145 (7)	0.0000 (6)	0.0014 (5)	0.0002 (6)
C33	0.0219 (8)	0.0285 (9)	0.0179 (7)	0.0001 (7)	0.0014 (6)	−0.0076 (6)
O8	0.0512 (8)	0.0200 (6)	0.0347 (7)	0.0055 (6)	0.0011 (6)	0.0000 (5)
C35	0.0177 (7)	0.0152 (7)	0.0189 (7)	0.0008 (6)	0.0018 (6)	0.0010 (6)
C11	0.0192 (7)	0.0190 (7)	0.0168 (7)	0.0001 (6)	0.0022 (6)	−0.0007 (6)
O9	0.0579 (9)	0.0408 (8)	0.0224 (7)	−0.0050 (7)	0.0103 (6)	−0.0030 (6)
O11	0.0415 (8)	0.0369 (8)	0.0384 (8)	−0.0133 (6)	0.0126 (6)	0.0047 (6)
O10	0.0316 (7)	0.0369 (8)	0.0707 (11)	0.0079 (6)	−0.0222 (7)	−0.0106 (8)
C23	0.0146 (7)	0.0200 (8)	0.0245 (8)	0.0001 (6)	0.0034 (6)	0.0121 (6)
C1	0.0283 (8)	0.0210 (8)	0.0208 (8)	0.0025 (6)	0.0049 (6)	0.0086 (6)

Geometric parameters (Å, º)

Cr1—O2	1.9268 (10)	C17—H17B	0.96
Cr1—O1	1.9356 (10)	C17—H17C	0.96
Cr1—O3	1.9684 (11)	C6—H6A	0.96
Cr1—N2	1.9976 (12)	C6—H6B	0.96
Cr1—N1	2.0547 (12)	C6—H6C	0.96
Cr1—N3	2.0676 (12)	C10—H10A	0.96
Cl1—O5	1.4352 (12)	C10—H10B	0.96
Cl1—O4	1.4376 (12)	C10—H10C	0.96
Cl1—O6	1.4430 (12)	O3—H45	0.72 (2)
Cl1—O7	1.4503 (12)	O3—H46	0.87 (3)
Cl2—O11	1.4222 (13)	C31—C32	1.379 (2)
Cl2—O9	1.4236 (14)	C31—C25	1.476 (2)
Cl2—O10	1.4405 (14)	C25—C24	1.385 (2)
Cl2—O8	1.4439 (13)	C22—C23	1.386 (2)
O1—C4	1.2776 (18)	C22—C21	1.389 (2)
O2—C2	1.2864 (18)	C22—H22	0.93
N2—C25	1.3418 (19)	C34—C33	1.380 (2)
N2—C21	1.3431 (19)	C34—C35	1.384 (2)
N3—C35	1.3403 (19)	C34—H34	0.93
N3—C31	1.3617 (19)	C13—C12	1.374 (2)
N1—C11	1.3376 (19)	C13—C14	1.389 (2)
N1—C15	1.3635 (19)	C13—H13	0.93
P1—O12	1.4953 (11)	C15—C14	1.377 (2)
P1—N4	1.6297 (13)	C15—C21	1.479 (2)
P1—N6	1.6356 (14)	C24—C23	1.391 (2)
P1—N5	1.6473 (14)	C24—H24	0.93
N4—C7	1.455 (2)	C14—H14	0.93
N4—C6	1.457 (2)	C12—C11	1.384 (2)
N5—C9	1.457 (2)	C12—H12	0.93
N5—C8	1.469 (2)	C2—C3	1.387 (2)
O13—H5A	0.75 (3)	C2—C1	1.495 (2)
O13—H5B	0.89 (3)	C4—C3	1.399 (2)
O14—H4B	0.80 (3)	C4—C5	1.496 (2)
O14—H4A	0.86 (3)	C3—H3	0.93
N6—C10	1.454 (2)	C5—H5C	0.96
N6—C17	1.458 (2)	C5—H5D	0.96
C7—H7A	0.96	C5—H5E	0.96
C7—H7B	0.96	C32—C33	1.385 (2)
C7—H7C	0.96	C32—H32	0.93
C8—H8A	0.96	C33—H33	0.93
C8—H8B	0.96	C35—H35	0.93
C8—H8C	0.96	C11—H11	0.93
C9—H9A	0.96	C23—H23	0.93
C9—H9B	0.96	C1—H1A	0.96
C9—H9C	0.96	C1—H1B	0.96
C17—H17A	0.96	C1—H1C	0.96
O2—Cr1—O1	91.05 (4)	N4—C6—H6B	109.5
O2—Cr1—O3	87.51 (5)	H6A—C6—H6B	109.5
O1—Cr1—O3	177.84 (5)	N4—C6—H6C	109.5
O2—Cr1—N2	176.74 (5)	H6A—C6—H6C	109.5
O1—Cr1—N2	90.76 (4)	H6B—C6—H6C	109.5
O3—Cr1—N2	90.76 (5)	N6—C10—H10A	109.5
O2—Cr1—N1	98.71 (5)	N6—C10—H10B	109.5
O1—Cr1—N1	90.80 (5)	H10A—C10—H10B	109.5
O3—Cr1—N1	91.00 (5)	N6—C10—H10C	109.5
N2—Cr1—N1	78.55 (5)	H10A—C10—H10C	109.5
O2—Cr1—N3	104.47 (5)	H10B—C10—H10C	109.5
O1—Cr1—N3	89.56 (5)	Cr1—O3—H45	118.6 (17)
O3—Cr1—N3	89.24 (5)	Cr1—O3—H46	115.2 (16)
N2—Cr1—N3	78.26 (5)	H45—O3—H46	113 (2)
N1—Cr1—N3	156.81 (5)	N3—C31—C32	121.40 (14)
O5—Cl1—O4	109.71 (8)	N3—C31—C25	114.47 (13)
O5—Cl1—O6	110.08 (7)	C32—C31—C25	124.13 (14)
O4—Cl1—O6	109.53 (8)	N2—C25—C24	120.25 (14)
O5—Cl1—O7	109.29 (7)	N2—C25—C31	113.06 (12)
O4—Cl1—O7	109.49 (7)	C24—C25—C31	126.68 (14)
O6—Cl1—O7	108.72 (7)	C23—C22—C21	118.31 (14)
O11—Cl2—O9	110.99 (9)	C23—C22—H22	120.8
O11—Cl2—O10	109.01 (10)	C21—C22—H22	120.8
O9—Cl2—O10	109.30 (10)	C33—C34—C35	119.05 (15)
O11—Cl2—O8	109.39 (9)	C33—C34—H34	120.5
O9—Cl2—O8	109.83 (9)	C35—C34—H34	120.5
O10—Cl2—O8	108.27 (8)	C12—C13—C14	119.61 (15)
C4—O1—Cr1	127.56 (9)	C12—C13—H13	120.2
C2—O2—Cr1	128.13 (9)	C14—C13—H13	120.2
C25—N2—C21	122.11 (13)	N1—C15—C14	121.21 (14)
C25—N2—Cr1	119.10 (10)	N1—C15—C21	114.15 (13)
C21—N2—Cr1	118.71 (10)	C14—C15—C21	124.63 (14)
C35—N3—C31	119.02 (13)	C25—C24—C23	118.39 (14)
C35—N3—Cr1	125.91 (10)	C25—C24—H24	120.8
C31—N3—Cr1	115.07 (10)	C23—C24—H24	120.8
C11—N1—C15	119.14 (13)	C15—C14—C13	119.07 (15)
C11—N1—Cr1	125.54 (10)	C15—C14—H14	120.5
C15—N1—Cr1	115.32 (10)	C13—C14—H14	120.5
O12—P1—N4	110.15 (7)	C13—C12—C11	118.86 (15)
O12—P1—N6	107.93 (7)	C13—C12—H12	120.6
N4—P1—N6	111.59 (7)	C11—C12—H12	120.6
O12—P1—N5	115.13 (7)	O2—C2—C3	124.09 (13)
N4—P1—N5	103.19 (7)	O2—C2—C1	114.96 (13)
N6—P1—N5	108.85 (7)	C3—C2—C1	120.94 (14)
C7—N4—C6	113.68 (13)	O1—C4—C3	124.53 (13)
C7—N4—P1	120.14 (11)	O1—C4—C5	115.50 (13)
C6—N4—P1	124.59 (11)	C3—C4—C5	119.97 (13)
C9—N5—C8	113.07 (14)	C2—C3—C4	124.34 (14)
C9—N5—P1	121.76 (12)	C2—C3—H3	117.8
C8—N5—P1	116.98 (11)	C4—C3—H3	117.8
H5A—O13—H5B	109 (2)	N2—C21—C22	120.24 (14)
H4B—O14—H4A	110 (3)	N2—C21—C15	113.14 (12)
C10—N6—C17	114.10 (14)	C22—C21—C15	126.62 (14)
C10—N6—P1	122.88 (12)	C4—C5—H5C	109.5
C17—N6—P1	121.96 (12)	C4—C5—H5D	109.5
N4—C7—H7A	109.5	H5C—C5—H5D	109.5
N4—C7—H7B	109.5	C4—C5—H5E	109.5
H7A—C7—H7B	109.5	H5C—C5—H5E	109.5
N4—C7—H7C	109.5	H5D—C5—H5E	109.5
H7A—C7—H7C	109.5	C31—C32—C33	119.22 (15)
H7B—C7—H7C	109.5	C31—C32—H32	120.4
N5—C8—H8A	109.5	C33—C32—H32	120.4
N5—C8—H8B	109.5	C34—C33—C32	119.33 (15)
H8A—C8—H8B	109.5	C34—C33—H33	120.3
N5—C8—H8C	109.5	C32—C33—H33	120.3
H8A—C8—H8C	109.5	N3—C35—C34	121.97 (14)
H8B—C8—H8C	109.5	N3—C35—H35	119
N5—C9—H9A	109.5	C34—C35—H35	119
N5—C9—H9B	109.5	N1—C11—C12	122.09 (15)
H9A—C9—H9B	109.5	N1—C11—H11	119
N5—C9—H9C	109.5	C12—C11—H11	119
H9A—C9—H9C	109.5	C22—C23—C24	120.68 (14)
H9B—C9—H9C	109.5	C22—C23—H23	119.7
N6—C17—H17A	109.5	C24—C23—H23	119.7
N6—C17—H17B	109.5	C2—C1—H1A	109.5
H17A—C17—H17B	109.5	C2—C1—H1B	109.5
N6—C17—H17C	109.5	H1A—C1—H1B	109.5
H17A—C17—H17C	109.5	C2—C1—H1C	109.5
H17B—C17—H17C	109.5	H1A—C1—H1C	109.5
N4—C6—H6A	109.5	H1B—C1—H1C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O14—H4A···O10	0.86 (3)	2.00 (3)	2.838 (2)	163 (3)
O14—H4B···O8^i	0.80 (3)	2.09 (3)	2.861 (2)	162 (2)
O3—H45···O13	0.72 (2)	1.93 (2)	2.6461 (17)	171 (2)
C1—H1A···O13^ii	0.96	2.77	3.384 (2)	123
C6—H6A···N5	0.96	2.52	3.007 (2)	111
C7—H7A···O12	0.96	2.47	2.976 (2)	113
C9—H9A···N6	0.96	2.54	3.043 (2)	113
C13—H13···O13^iii	0.93	2.48	3.289 (2)	145
O14—H4A···O10	0.86 (3)	2.00 (3)	2.838 (2)	163 (3)
O14—H4B···O8^i	0.80 (3)	2.09 (3)	2.861 (2)	162 (2)
O3—H45···O13	0.72 (2)	1.93 (2)	2.6461 (17)	171 (2)
C1—H1A···O13^ii	0.96	2.77	3.384 (2)	123
C6—H6A···N5	0.96	2.52	3.007 (2)	111
C7—H7A···O12	0.96	2.47	2.976 (2)	113
C9—H9A···N6	0.96	2.54	3.043 (2)	113
C13—H13···O13^iii	0.93	2.48	3.289 (2)	145
C17—H17A···O12	0.96	2.49	2.970 (2)	111
O13—H5A···O7^iii	0.75 (3)	2.14 (3)	2.8830 (18)	172 (3)
O13—H5B···O14^iv	0.89 (3)	1.84 (3)	2.7356 (19)	177 (2)
O3—H46···O12^v	0.87 (3)	1.63 (3)	2.4989 (16)	175 (3)
C6—H6C···O9^vi	0.96	2.57	3.466 (2)	155
C11—H11···O6^iii	0.93	2.59	3.322 (2)	136
C14—H14···O6^vii	0.93	2.48	3.199 (2)	134
C22—H22···O4^vii	0.93	2.47	3.367 (2)	163
C24—H24···O8^viii	0.93	2.53	3.415 (2)	159
C32—H32···O14^ix	0.93	2.57	3.289 (2)	135
C35—H35···O7	0.93	2.51	3.3811 (19)	156
C17—H17A···O12	0.96	2.49	2.970 (2)	111

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