Creatininium bis-(pyridine-2,6-dicarboxyl-ato)chromate(III) pyridine-2,6-dicarboxylic acid hexa-hydrate.

The title compound, (C(4)H(8)N(3)O)[Cr(C(7)H(3)NO(4))(2)]·C(7)H(5)NO(4)·6H(2)O, was obtained by the reaction of Cr(NO(3))(3)·9H(2)O with pyridine-2,6-dicarboxylic acid (pydcH(2)) and creatinine (creat) in aqueous solution (molar ratio 1:2:2). The cation is a protonated creatinine (creatH(+)) while the anion is a bis-pydc(2-) Cr(III) complex. The Cr(III) is coordinated by four oxygen and two nitro-gen atoms of two (pydc)(2-) groups and has a disorted octa-hedral coordination environment. The structure also contains a neutral mol-ecule of pydcH(2) that is hydrogen bonded to the creatH(+) and six mol-ecules of water. Extensive inter-molecular inter-actions, including seventeen classical hydrogen bonds, two weak C-H⋯O bonds, and C-O⋯π stacking inter-actions, with O⋯centroid distances of 3.211 (13) and 3.300 (12) Å, connect the various components in the crystal structure.

Related literature

For a recent review on proton-transfer compounds and their structures, see: Aghabozorg, Manteghi et al. (2008 ▶). For related creatininium structures, see: Aghabozorg, Ramezanipour et al. (2008 ▶); Moghimi et al. (2004 ▶, 2005 ▶).

Experimental

Crystal data

(C4H8N3O)[Cr(C7H3NO4)2]·C7H5NO4·6H2O

M = 771.56

Triclinic,

a = 9.0860 (5) Å

b = 13.6274 (8) Å

c = 14.7301 (8) Å

α = 65.481 (2)°

β = 74.685 (2)°

γ = 77.644 (2)°

V = 1589.10 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.46 mm−1

T = 90 (2) K

0.33 × 0.32 × 0.10 mm

Data collection

Bruker SMART APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.864, T max = 0.956

20278 measured reflections

7266 independent reflections

6654 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.077

S = 1.01

7266 reflections

584 parameters

All H-atom parameters refined

Δρmax = 0.41 e Å−3

Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808027700/sj2533sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027700/sj2533Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C4H8N3O)[Cr(C7H3NO4)2]·C7H5NO4·6H2O	Z = 2
Mr = 771.56	F(000) = 798
Triclinic, P1	Dx = 1.612 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0860 (5) Å	Cell parameters from 6379 reflections
b = 13.6274 (8) Å	θ = 3.0–31.5°
c = 14.7301 (8) Å	µ = 0.46 mm−1
α = 65.481 (2)°	T = 90 K
β = 74.685 (2)°	Plate, violet
γ = 77.644 (2)°	0.33 × 0.32 × 0.10 mm
V = 1589.10 (15) Å3

Bruker SMART APEXII diffractometer	7266 independent reflections
Radiation source: fine-focus sealed tube	6654 reflections with I > 2σ(I)
graphite	Rint = 0.019
Detector resolution: 8.3 pixels mm-1	θmax = 27.5°, θmin = 2.7°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −17→17
Tmin = 0.864, Tmax = 0.956	l = −19→19
20278 measured reflections

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077	All H-atom parameters refined
S = 1.02	w = 1/[σ2(Fo2) + (0.0385P)2 + 0.9325P] where P = (Fo2 + 2Fc2)/3
7266 reflections	(Δ/σ)max = 0.001
584 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.46 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cr1	0.25265 (2)	0.216209 (16)	0.359634 (15)	0.01061 (6)
O1	0.36533 (10)	0.23292 (7)	0.45071 (7)	0.01405 (18)
O2	0.46030 (11)	0.14296 (8)	0.59416 (7)	0.0175 (2)
O3	0.15065 (11)	0.14097 (8)	0.30655 (7)	0.01496 (19)
O4	0.07696 (12)	−0.01935 (8)	0.33737 (8)	0.0200 (2)
O5	0.43892 (10)	0.22188 (7)	0.25150 (7)	0.01432 (19)
O6	0.55182 (11)	0.32381 (8)	0.09398 (7)	0.0181 (2)
O7	0.05282 (10)	0.26969 (7)	0.43082 (7)	0.01383 (18)
O8	−0.14469 (11)	0.40222 (8)	0.41140 (8)	0.0189 (2)
N1	0.26631 (12)	0.06706 (9)	0.46327 (8)	0.0116 (2)
N2	0.21136 (12)	0.36451 (9)	0.25887 (8)	0.0120 (2)
C1	0.38970 (14)	0.14811 (10)	0.53165 (10)	0.0130 (2)
C2	0.32378 (14)	0.04896 (10)	0.54427 (10)	0.0126 (2)
C3	0.31731 (15)	−0.05060 (11)	0.62527 (10)	0.0154 (3)
H3	0.3540 (19)	−0.0619 (13)	0.6818 (13)	0.016 (4)*
C4	0.25291 (15)	−0.13028 (11)	0.61755 (10)	0.0166 (3)
H4	0.2463 (19)	−0.1981 (14)	0.6707 (13)	0.017 (4)*
C5	0.19581 (15)	−0.11032 (11)	0.53165 (11)	0.0156 (3)
H5	0.150 (2)	−0.1614 (14)	0.5244 (13)	0.020 (4)*
C6	0.20238 (14)	−0.00750 (10)	0.45504 (10)	0.0131 (2)
C7	0.13731 (14)	0.03755 (11)	0.35899 (10)	0.0140 (2)
C8	0.44766 (15)	0.30926 (10)	0.16929 (10)	0.0133 (2)
C9	0.31394 (14)	0.39718 (10)	0.17162 (10)	0.0128 (2)
C10	0.28865 (16)	0.49990 (11)	0.09810 (10)	0.0154 (3)
H10	0.357 (2)	0.5255 (15)	0.0365 (14)	0.023 (4)*
C11	0.15425 (16)	0.56585 (11)	0.11809 (10)	0.0164 (3)
H11	0.135 (2)	0.6360 (15)	0.0687 (14)	0.023 (4)*
C12	0.04727 (15)	0.52912 (11)	0.20890 (10)	0.0152 (3)
H12	−0.0436 (19)	0.5732 (14)	0.2231 (12)	0.015 (4)*
C13	0.08062 (14)	0.42558 (10)	0.27889 (10)	0.0127 (2)
C14	−0.01527 (15)	0.36454 (10)	0.38121 (10)	0.0134 (2)
O13	0.05039 (12)	1.18680 (8)	−0.06791 (8)	0.0204 (2)
N4	0.39073 (15)	0.87378 (10)	0.02195 (10)	0.0175 (2)
H4A	0.476 (2)	0.8454 (16)	0.0006 (15)	0.029 (5)*
H4B	0.340 (2)	0.8382 (16)	0.0802 (16)	0.028 (5)*
N5	0.19415 (13)	1.02123 (9)	−0.00184 (9)	0.0156 (2)
H5A	0.140 (2)	0.9944 (16)	0.0570 (16)	0.032 (5)*
N6	0.39959 (13)	1.03426 (9)	−0.12569 (9)	0.0156 (2)
C22	0.30056 (16)	1.13631 (11)	−0.16289 (11)	0.0172 (3)
H22A	0.350 (2)	1.1955 (15)	−0.1755 (14)	0.024 (4)*
H22B	0.2690 (19)	1.1442 (13)	−0.2225 (13)	0.015 (4)*
C23	0.54951 (16)	1.00844 (13)	−0.18301 (11)	0.0193 (3)
H23A	0.540 (3)	0.9830 (19)	−0.2282 (19)	0.051 (7)*
H23B	0.617 (3)	0.959 (2)	−0.1406 (19)	0.055 (7)*
H23C	0.599 (3)	1.070 (2)	−0.217 (2)	0.065 (8)*
C24	0.33392 (15)	0.97084 (11)	−0.03381 (10)	0.0145 (2)
C25	0.16432 (16)	1.12269 (11)	−0.07475 (10)	0.0161 (3)
O9	0.22431 (12)	0.75720 (8)	0.21745 (8)	0.0222 (2)
O10	0.16856 (11)	0.60735 (8)	0.35557 (7)	0.0185 (2)
H10A	0.080 (3)	0.6511 (19)	0.3638 (17)	0.045 (6)*
O11	0.69061 (11)	0.75755 (8)	−0.01882 (8)	0.0204 (2)
O12	0.86113 (11)	0.60775 (8)	0.00786 (8)	0.0185 (2)
H12A	0.915 (3)	0.649 (2)	−0.0534 (19)	0.051 (7)*
N3	0.50100 (13)	0.65317 (9)	0.16037 (9)	0.0143 (2)
C15	0.25904 (15)	0.66364 (11)	0.27266 (10)	0.0158 (3)
C16	0.41037 (15)	0.59999 (11)	0.24827 (10)	0.0149 (3)
C17	0.44864 (16)	0.49323 (11)	0.31185 (10)	0.0167 (3)
H17	0.381 (2)	0.4595 (15)	0.3761 (14)	0.024 (4)*
C18	0.58702 (16)	0.43822 (11)	0.28135 (11)	0.0181 (3)
H18	0.613 (2)	0.3676 (16)	0.3202 (14)	0.023 (4)*
C19	0.68190 (16)	0.49118 (11)	0.18923 (11)	0.0167 (3)
H19	0.777 (2)	0.4580 (14)	0.1653 (13)	0.021 (4)*
C20	0.63432 (15)	0.59888 (11)	0.13218 (10)	0.0145 (2)
C21	0.73088 (15)	0.66371 (11)	0.03255 (10)	0.0152 (3)
O14	−0.28792 (14)	0.61850 (10)	0.36097 (10)	0.0268 (2)
H14A	−0.377 (3)	0.6268 (19)	0.3838 (18)	0.048 (7)*
H14B	−0.258 (3)	0.553 (2)	0.3801 (17)	0.041 (6)*
O15	−0.08716 (12)	0.72137 (9)	0.38192 (8)	0.0220 (2)
H15A	−0.160 (3)	0.6886 (18)	0.3832 (17)	0.040 (6)*
H15B	−0.098 (3)	0.7271 (18)	0.4335 (18)	0.039 (6)*
O16	0.00515 (12)	−0.05810 (9)	0.18249 (8)	0.0188 (2)
H16A	0.008 (3)	−0.0312 (19)	0.2190 (18)	0.041 (6)*
H16B	0.043 (3)	−0.122 (2)	0.2076 (18)	0.049 (7)*
O17	−0.02251 (12)	0.28295 (9)	0.16386 (8)	0.0189 (2)
H17A	−0.076 (3)	0.2496 (18)	0.1493 (16)	0.039 (6)*
H17B	0.029 (3)	0.2388 (19)	0.2012 (18)	0.041 (6)*
O18	0.59381 (13)	0.31757 (10)	0.57788 (9)	0.0256 (2)
H18A	0.571 (3)	0.2635 (19)	0.5733 (16)	0.040 (6)*
H18B	0.673 (3)	0.3345 (19)	0.5322 (19)	0.048 (7)*
O19	0.81371 (13)	0.17421 (9)	0.11655 (9)	0.0220 (2)
H19A	0.731 (3)	0.215 (2)	0.1020 (18)	0.050 (7)*
H19B	0.867 (3)	0.1690 (18)	0.0646 (18)	0.043 (6)*

	U11	U22	U33	U12	U13	U23
Cr1	0.01120 (10)	0.00907 (10)	0.00929 (10)	−0.00114 (7)	−0.00217 (7)	−0.00125 (8)
O1	0.0153 (4)	0.0122 (4)	0.0137 (4)	−0.0024 (3)	−0.0039 (3)	−0.0029 (4)
O2	0.0175 (5)	0.0198 (5)	0.0164 (5)	−0.0028 (4)	−0.0066 (4)	−0.0059 (4)
O3	0.0158 (4)	0.0152 (4)	0.0136 (4)	−0.0018 (3)	−0.0041 (3)	−0.0045 (4)
O4	0.0214 (5)	0.0206 (5)	0.0232 (5)	−0.0033 (4)	−0.0063 (4)	−0.0118 (4)
O5	0.0134 (4)	0.0126 (4)	0.0127 (4)	−0.0005 (3)	−0.0017 (3)	−0.0016 (4)
O6	0.0162 (5)	0.0165 (5)	0.0146 (5)	−0.0017 (4)	0.0017 (4)	−0.0023 (4)
O7	0.0140 (4)	0.0125 (4)	0.0125 (4)	−0.0016 (3)	−0.0020 (3)	−0.0026 (4)
O8	0.0144 (5)	0.0185 (5)	0.0191 (5)	0.0005 (4)	−0.0003 (4)	−0.0055 (4)
N1	0.0101 (5)	0.0106 (5)	0.0120 (5)	−0.0004 (4)	−0.0012 (4)	−0.0034 (4)
N2	0.0126 (5)	0.0112 (5)	0.0116 (5)	−0.0019 (4)	−0.0032 (4)	−0.0030 (4)
C1	0.0110 (6)	0.0134 (6)	0.0124 (6)	−0.0004 (5)	−0.0004 (4)	−0.0044 (5)
C2	0.0092 (5)	0.0133 (6)	0.0131 (6)	0.0004 (4)	−0.0014 (4)	−0.0043 (5)
C3	0.0130 (6)	0.0161 (6)	0.0128 (6)	0.0011 (5)	−0.0018 (5)	−0.0029 (5)
C4	0.0145 (6)	0.0107 (6)	0.0163 (6)	0.0001 (5)	0.0008 (5)	−0.0003 (5)
C5	0.0120 (6)	0.0117 (6)	0.0204 (7)	−0.0015 (5)	0.0006 (5)	−0.0057 (5)
C6	0.0097 (5)	0.0131 (6)	0.0154 (6)	−0.0002 (4)	−0.0004 (5)	−0.0061 (5)
C7	0.0109 (6)	0.0161 (6)	0.0144 (6)	0.0006 (5)	−0.0007 (5)	−0.0072 (5)
C8	0.0137 (6)	0.0120 (6)	0.0134 (6)	−0.0020 (5)	−0.0040 (5)	−0.0029 (5)
C9	0.0123 (6)	0.0132 (6)	0.0126 (6)	−0.0029 (5)	−0.0030 (5)	−0.0036 (5)
C10	0.0161 (6)	0.0142 (6)	0.0129 (6)	−0.0037 (5)	−0.0024 (5)	−0.0017 (5)
C11	0.0194 (7)	0.0105 (6)	0.0160 (6)	−0.0018 (5)	−0.0064 (5)	−0.0002 (5)
C12	0.0151 (6)	0.0132 (6)	0.0170 (6)	−0.0002 (5)	−0.0049 (5)	−0.0050 (5)
C13	0.0124 (6)	0.0134 (6)	0.0137 (6)	−0.0023 (5)	−0.0034 (5)	−0.0056 (5)
C14	0.0143 (6)	0.0134 (6)	0.0133 (6)	−0.0031 (5)	−0.0030 (5)	−0.0050 (5)
O13	0.0199 (5)	0.0185 (5)	0.0230 (5)	0.0060 (4)	−0.0071 (4)	−0.0104 (4)
N4	0.0171 (6)	0.0156 (6)	0.0160 (6)	0.0020 (5)	−0.0035 (5)	−0.0040 (5)
N5	0.0153 (5)	0.0152 (5)	0.0145 (6)	0.0010 (4)	−0.0026 (4)	−0.0054 (5)
N6	0.0154 (5)	0.0135 (5)	0.0152 (5)	0.0013 (4)	−0.0033 (4)	−0.0041 (4)
C22	0.0189 (7)	0.0134 (6)	0.0171 (6)	0.0017 (5)	−0.0046 (5)	−0.0046 (5)
C23	0.0163 (7)	0.0232 (7)	0.0163 (7)	0.0009 (5)	−0.0020 (5)	−0.0078 (6)
C24	0.0153 (6)	0.0153 (6)	0.0149 (6)	−0.0005 (5)	−0.0052 (5)	−0.0071 (5)
C25	0.0187 (6)	0.0158 (6)	0.0168 (6)	−0.0008 (5)	−0.0065 (5)	−0.0078 (5)
O9	0.0191 (5)	0.0192 (5)	0.0199 (5)	0.0038 (4)	−0.0009 (4)	−0.0042 (4)
O10	0.0149 (5)	0.0199 (5)	0.0187 (5)	−0.0026 (4)	0.0000 (4)	−0.0071 (4)
O11	0.0169 (5)	0.0182 (5)	0.0198 (5)	0.0005 (4)	−0.0032 (4)	−0.0027 (4)
O12	0.0156 (5)	0.0191 (5)	0.0175 (5)	0.0007 (4)	−0.0008 (4)	−0.0066 (4)
N3	0.0138 (5)	0.0145 (5)	0.0154 (5)	−0.0008 (4)	−0.0040 (4)	−0.0062 (4)
C15	0.0154 (6)	0.0177 (6)	0.0151 (6)	−0.0021 (5)	−0.0036 (5)	−0.0067 (5)
C16	0.0157 (6)	0.0154 (6)	0.0156 (6)	−0.0021 (5)	−0.0044 (5)	−0.0070 (5)
C17	0.0184 (6)	0.0154 (6)	0.0163 (6)	−0.0041 (5)	−0.0037 (5)	−0.0050 (5)
C18	0.0209 (7)	0.0124 (6)	0.0200 (7)	−0.0008 (5)	−0.0073 (5)	−0.0038 (5)
C19	0.0156 (6)	0.0155 (6)	0.0206 (7)	0.0006 (5)	−0.0057 (5)	−0.0084 (5)
C20	0.0148 (6)	0.0151 (6)	0.0155 (6)	−0.0017 (5)	−0.0048 (5)	−0.0066 (5)
C21	0.0139 (6)	0.0178 (6)	0.0161 (6)	−0.0014 (5)	−0.0046 (5)	−0.0077 (5)
O14	0.0180 (6)	0.0181 (6)	0.0398 (7)	0.0000 (4)	−0.0020 (5)	−0.0100 (5)
O15	0.0191 (5)	0.0293 (6)	0.0188 (5)	−0.0005 (4)	−0.0025 (4)	−0.0122 (5)
O16	0.0224 (5)	0.0170 (5)	0.0175 (5)	0.0006 (4)	−0.0048 (4)	−0.0080 (4)
O17	0.0174 (5)	0.0201 (5)	0.0166 (5)	0.0003 (4)	−0.0054 (4)	−0.0044 (4)
O18	0.0191 (5)	0.0295 (6)	0.0342 (6)	−0.0083 (4)	0.0033 (5)	−0.0204 (5)
O19	0.0187 (5)	0.0239 (5)	0.0215 (5)	0.0022 (4)	−0.0059 (4)	−0.0080 (4)

Cr1—N1	1.9733 (11)	N5—C25	1.3782 (17)
Cr1—N2	1.9769 (11)	N5—H5A	0.85 (2)
Cr1—O5	1.9842 (9)	N6—C24	1.3259 (17)
Cr1—O3	1.9942 (10)	N6—C23	1.4581 (18)
Cr1—O1	1.9947 (9)	N6—C22	1.4616 (17)
Cr1—O7	1.9974 (9)	C22—C25	1.5171 (19)
O1—C1	1.3009 (15)	C22—H22A	0.938 (19)
O2—C1	1.2262 (16)	C22—H22B	0.952 (17)
O3—C7	1.3106 (16)	C23—H23A	0.90 (3)
O4—C7	1.2176 (17)	C23—H23B	0.95 (3)
O5—C8	1.2975 (15)	C23—H23C	0.92 (3)
O6—C8	1.2283 (16)	O9—C15	1.2204 (17)
O7—C14	1.3039 (16)	O10—C15	1.3107 (17)
O8—C14	1.2244 (16)	O10—H10A	0.91 (2)
N1—C6	1.3329 (17)	O11—C21	1.2184 (17)
N1—C2	1.3366 (17)	O12—C21	1.3157 (16)
N2—C13	1.3365 (17)	O12—H12A	0.91 (2)
N2—C9	1.3373 (16)	N3—C20	1.3390 (17)
C1—C2	1.5160 (18)	N3—C16	1.3391 (17)
C2—C3	1.3861 (18)	C15—C16	1.5031 (18)
C3—C4	1.394 (2)	C16—C17	1.3926 (19)
C3—H3	0.920 (17)	C17—C18	1.386 (2)
C4—C5	1.395 (2)	C17—H17	0.970 (18)
C4—H4	0.932 (17)	C18—C19	1.393 (2)
C5—C6	1.3886 (18)	C18—H18	0.909 (19)
C5—H5	0.934 (18)	C19—C20	1.3942 (19)
C6—C7	1.5145 (18)	C19—H19	0.935 (18)
C8—C9	1.5172 (18)	C20—C21	1.5099 (19)
C9—C10	1.3859 (18)	O14—H14A	0.79 (3)
C10—C11	1.3949 (19)	O14—H14B	0.83 (2)
C10—H10	0.927 (19)	O15—H15A	0.86 (2)
C11—C12	1.3965 (19)	O15—H15B	0.77 (2)
C11—H11	0.944 (18)	O16—H16A	0.78 (2)
C12—C13	1.3858 (18)	O16—H16B	0.83 (3)
C12—H12	0.942 (17)	O17—H17A	0.85 (2)
C13—C14	1.5161 (18)	O17—H17B	0.79 (2)
O13—C25	1.2149 (17)	O18—H18A	0.84 (2)
N4—C24	1.3117 (18)	O18—H18B	0.84 (3)
N4—H4A	0.83 (2)	O19—H19A	0.85 (3)
N4—H4B	0.85 (2)	O19—H19B	0.81 (2)
N5—C24	1.3731 (17)
N1—Cr1—N2	172.88 (4)	N2—C13—C14	110.86 (11)
N1—Cr1—O5	106.16 (4)	C12—C13—C14	128.84 (12)
N2—Cr1—O5	79.39 (4)	O8—C14—O7	124.76 (12)
N1—Cr1—O3	78.84 (4)	O8—C14—C13	121.81 (12)
N2—Cr1—O3	96.78 (4)	O7—C14—C13	113.42 (11)
O5—Cr1—O3	91.39 (4)	C24—N4—H4A	120.6 (14)
N1—Cr1—O1	79.13 (4)	C24—N4—H4B	120.3 (13)
N2—Cr1—O1	105.30 (4)	H4A—N4—H4B	119.1 (19)
O5—Cr1—O1	93.27 (4)	C24—N5—C25	110.51 (11)
O3—Cr1—O1	157.91 (4)	C24—N5—H5A	123.0 (14)
N1—Cr1—O7	96.08 (4)	C25—N5—H5A	126.3 (14)
N2—Cr1—O7	78.42 (4)	C24—N6—C23	125.88 (12)
O5—Cr1—O7	157.76 (4)	C24—N6—C22	110.40 (11)
O3—Cr1—O7	92.80 (4)	C23—N6—C22	123.72 (11)
O1—Cr1—O7	91.01 (4)	N6—C22—C25	102.34 (11)
C1—O1—Cr1	117.31 (8)	N6—C22—H22A	110.6 (11)
C7—O3—Cr1	117.92 (8)	C25—C22—H22A	111.4 (11)
C8—O5—Cr1	117.46 (8)	N6—C22—H22B	111.1 (10)
C14—O7—Cr1	117.96 (8)	C25—C22—H22B	110.6 (10)
C6—N1—C2	123.01 (11)	H22A—C22—H22B	110.6 (15)
C6—N1—Cr1	118.48 (9)	N6—C23—H23A	111.2 (15)
C2—N1—Cr1	118.06 (9)	N6—C23—H23B	112.8 (15)
C13—N2—C9	123.11 (11)	H23A—C23—H23B	110 (2)
C13—N2—Cr1	118.99 (9)	N6—C23—H23C	109.5 (17)
C9—N2—Cr1	117.84 (9)	H23A—C23—H23C	109 (2)
O2—C1—O1	126.04 (12)	H23B—C23—H23C	104 (2)
O2—C1—C2	120.05 (11)	N4—C24—N6	126.64 (13)
O1—C1—C2	113.91 (11)	N4—C24—N5	122.86 (13)
N1—C2—C3	120.18 (12)	N6—C24—N5	110.49 (11)
N1—C2—C1	111.06 (11)	O13—C25—N5	125.75 (13)
C3—C2—C1	128.76 (12)	O13—C25—C22	128.00 (13)
C2—C3—C4	117.72 (12)	N5—C25—C22	106.25 (11)
C2—C3—H3	119.9 (11)	C15—O10—H10A	107.6 (14)
C4—C3—H3	122.4 (10)	C21—O12—H12A	110.0 (15)
C3—C4—C5	121.20 (12)	C20—N3—C16	117.38 (11)
C3—C4—H4	120.1 (10)	O9—C15—O10	124.43 (13)
C5—C4—H4	118.7 (11)	O9—C15—C16	122.17 (12)
C6—C5—C4	117.61 (12)	O10—C15—C16	113.34 (12)
C6—C5—H5	118.9 (11)	N3—C16—C17	123.71 (12)
C4—C5—H5	123.5 (11)	N3—C16—C15	114.63 (11)
N1—C6—C5	120.24 (12)	C17—C16—C15	121.64 (12)
N1—C6—C7	111.66 (11)	C18—C17—C16	118.11 (13)
C5—C6—C7	128.04 (12)	C18—C17—H17	121.6 (11)
O4—C7—O3	125.86 (12)	C16—C17—H17	120.3 (11)
O4—C7—C6	121.13 (12)	C17—C18—C19	119.22 (13)
O3—C7—C6	112.99 (11)	C17—C18—H18	119.9 (12)
O6—C8—O5	125.49 (12)	C19—C18—H18	120.8 (12)
O6—C8—C9	120.42 (11)	C18—C19—C20	118.15 (13)
O5—C8—C9	114.09 (11)	C18—C19—H19	122.6 (11)
N2—C9—C10	119.86 (12)	C20—C19—H19	119.2 (11)
N2—C9—C8	111.14 (11)	N3—C20—C19	123.42 (12)
C10—C9—C8	129.00 (12)	N3—C20—C21	114.59 (11)
C9—C10—C11	118.03 (12)	C19—C20—C21	122.00 (12)
C9—C10—H10	122.6 (11)	O11—C21—O12	124.35 (13)
C11—C10—H10	119.4 (11)	O11—C21—C20	122.94 (12)
C10—C11—C12	121.08 (12)	O12—C21—C20	112.71 (11)
C10—C11—H11	118.9 (11)	H14A—O14—H14B	109 (2)
C12—C11—H11	120.0 (11)	H15A—O15—H15B	110 (2)
C13—C12—C11	117.60 (12)	H16A—O16—H16B	106 (2)
C13—C12—H12	120.7 (10)	H17A—O17—H17B	108 (2)
C11—C12—H12	121.7 (10)	H18A—O18—H18B	104 (2)
N2—C13—C12	120.29 (12)	H19A—O19—H19B	108 (2)
N1—Cr1—O1—C1	−2.46 (9)	C5—C6—C7—O4	−4.4 (2)
N2—Cr1—O1—C1	171.81 (9)	N1—C6—C7—O3	−2.96 (15)
O5—Cr1—O1—C1	−108.30 (9)	C5—C6—C7—O3	174.13 (12)
O3—Cr1—O1—C1	−6.46 (16)	Cr1—O5—C8—O6	−176.91 (10)
O7—Cr1—O1—C1	93.54 (9)	Cr1—O5—C8—C9	2.87 (14)
N1—Cr1—O3—C7	0.88 (9)	C13—N2—C9—C10	1.76 (19)
N2—Cr1—O3—C7	−173.43 (9)	Cr1—N2—C9—C10	179.04 (10)
O5—Cr1—O3—C7	107.08 (9)	C13—N2—C9—C8	−177.99 (11)
O1—Cr1—O3—C7	4.89 (16)	Cr1—N2—C9—C8	−0.71 (14)
O7—Cr1—O3—C7	−94.76 (9)	O6—C8—C9—N2	178.40 (12)
N1—Cr1—O5—C8	172.87 (9)	O5—C8—C9—N2	−1.39 (16)
N2—Cr1—O5—C8	−2.55 (9)	O6—C8—C9—C10	−1.3 (2)
O3—Cr1—O5—C8	94.09 (9)	O5—C8—C9—C10	178.89 (13)
O1—Cr1—O5—C8	−107.51 (9)	N2—C9—C10—C11	−0.54 (19)
O7—Cr1—O5—C8	−6.78 (16)	C8—C9—C10—C11	179.17 (12)
N1—Cr1—O7—C14	−170.15 (9)	C9—C10—C11—C12	−0.8 (2)
N2—Cr1—O7—C14	5.26 (9)	C10—C11—C12—C13	0.9 (2)
O5—Cr1—O7—C14	9.50 (16)	C9—N2—C13—C12	−1.60 (19)
O3—Cr1—O7—C14	−91.09 (9)	Cr1—N2—C13—C12	−178.85 (9)
O1—Cr1—O7—C14	110.67 (9)	C9—N2—C13—C14	177.15 (11)
O5—Cr1—N1—C6	−90.96 (10)	Cr1—N2—C13—C14	−0.10 (14)
O3—Cr1—N1—C6	−2.76 (9)	C11—C12—C13—N2	0.21 (19)
O1—Cr1—N1—C6	178.77 (10)	C11—C12—C13—C14	−178.29 (12)
O7—Cr1—N1—C6	88.91 (10)	Cr1—O7—C14—O8	172.16 (10)
O5—Cr1—N1—C2	96.49 (9)	Cr1—O7—C14—C13	−6.72 (14)
O3—Cr1—N1—C2	−175.31 (10)	N2—C13—C14—O8	−174.56 (12)
O1—Cr1—N1—C2	6.22 (9)	C12—C13—C14—O8	4.0 (2)
O7—Cr1—N1—C2	−83.64 (9)	N2—C13—C14—O7	4.35 (15)
O5—Cr1—N2—C13	179.09 (10)	C12—C13—C14—O7	−177.04 (13)
O3—Cr1—N2—C13	88.95 (10)	C24—N6—C22—C25	1.04 (14)
O1—Cr1—N2—C13	−90.40 (10)	C23—N6—C22—C25	−178.54 (12)
O7—Cr1—N2—C13	−2.54 (9)	C23—N6—C24—N4	−0.3 (2)
O5—Cr1—N2—C9	1.70 (9)	C22—N6—C24—N4	−179.89 (13)
O3—Cr1—N2—C9	−88.45 (9)	C23—N6—C24—N5	178.95 (12)
O1—Cr1—N2—C9	92.21 (9)	C22—N6—C24—N5	−0.61 (15)
O7—Cr1—N2—C9	−179.93 (10)	C25—N5—C24—N4	179.15 (12)
Cr1—O1—C1—O2	177.87 (10)	C25—N5—C24—N6	−0.15 (16)
Cr1—O1—C1—C2	−1.13 (14)	C24—N5—C25—O13	−179.32 (13)
C6—N1—C2—C3	−0.63 (19)	C24—N5—C25—C22	0.81 (15)
Cr1—N1—C2—C3	171.56 (9)	N6—C22—C25—O13	179.04 (13)
C6—N1—C2—C1	179.57 (11)	N6—C22—C25—N5	−1.09 (14)
Cr1—N1—C2—C1	−8.24 (13)	C20—N3—C16—C17	1.25 (19)
O2—C1—C2—N1	−173.12 (11)	C20—N3—C16—C15	−176.95 (11)
O1—C1—C2—N1	5.95 (15)	O9—C15—C16—N3	−1.70 (19)
O2—C1—C2—C3	7.1 (2)	O10—C15—C16—N3	175.76 (11)
O1—C1—C2—C3	−173.83 (12)	O9—C15—C16—C17	−179.95 (13)
N1—C2—C3—C4	1.51 (19)	O10—C15—C16—C17	−2.48 (18)
C1—C2—C3—C4	−178.72 (12)	N3—C16—C17—C18	−1.4 (2)
C2—C3—C4—C5	−0.50 (19)	C15—C16—C17—C18	176.71 (12)
C3—C4—C5—C6	−1.35 (19)	C16—C17—C18—C19	0.1 (2)
C2—N1—C6—C5	−1.34 (19)	C17—C18—C19—C20	1.2 (2)
Cr1—N1—C6—C5	−173.49 (9)	C16—N3—C20—C19	0.16 (19)
C2—N1—C6—C7	176.01 (11)	C16—N3—C20—C21	−179.88 (11)
Cr1—N1—C6—C7	3.86 (14)	C18—C19—C20—N3	−1.4 (2)
C4—C5—C6—N1	2.27 (19)	C18—C19—C20—C21	178.67 (12)
C4—C5—C6—C7	−174.60 (12)	N3—C20—C21—O11	−0.66 (19)
Cr1—O3—C7—O4	179.27 (10)	C19—C20—C21—O11	179.30 (13)
Cr1—O3—C7—C6	0.84 (13)	N3—C20—C21—O12	179.64 (11)
N1—C6—C7—O4	178.53 (12)	C19—C20—C21—O12	−0.40 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O11	0.83 (2)	2.08 (2)	2.8934 (16)	167.3 (19)
N4—H4B···O9	0.85 (2)	1.98 (2)	2.8343 (16)	178.5 (8)
O10—H10A···O15	0.91 (2)	1.63 (2)	2.5382 (15)	176 (2)
O14—H14B···O8	0.83 (2)	2.01 (2)	2.8255 (16)	169 (2)
O15—H15A···O14	0.86 (2)	1.82 (2)	2.6718 (17)	168 (2)
O16—H16A···O4	0.78 (2)	2.07 (2)	2.8006 (15)	156 (2)
O17—H17B···O3	0.79 (2)	1.99 (2)	2.7758 (14)	172 (2)
O18—H18A···O2	0.84 (2)	1.98 (2)	2.7927 (15)	162 (2)
O19—H19A···O6	0.85 (3)	1.95 (3)	2.7763 (15)	164 (2)
N5—H5A···O16i	0.85 (2)	1.87 (2)	2.7175 (16)	175 (2)
O12—H12A···O17ii	0.91 (2)	1.66 (3)	2.5720 (14)	176 (2)
O14—H14A···O18iii	0.79 (3)	1.98 (3)	2.7546 (17)	167 (2)
O15—H15B···O7iii	0.77 (2)	2.16 (2)	2.9105 (15)	162 (2)
O16—H16B···O9iv	0.83 (3)	2.05 (3)	2.8083 (15)	152 (2)
O17—H17A···O19v	0.85 (2)	1.84 (2)	2.6916 (16)	178 (2)
O18—H18B···O8vi	0.84 (3)	2.12 (3)	2.9558 (15)	171 (2)
O19—H19B···O13vii	0.81 (2)	2.17 (2)	2.9531 (16)	162 (2)
C5—H5···O7viii	0.94 (2)	2.392 (19)	3.251 (2)	152.2 (15)
C10—H10···O6ii	0.929 (19)	2.283 (19)	3.0919 (17)	145.4 (18)

Cr1—N1	1.9733 (11)
Cr1—N2	1.9769 (11)
Cr1—O5	1.9842 (9)
Cr1—O3	1.9942 (10)
Cr1—O1	1.9947 (9)
Cr1—O7	1.9974 (9)

N1—Cr1—N2	172.88 (4)
N1—Cr1—O5	106.16 (4)
N2—Cr1—O5	79.39 (4)
N1—Cr1—O3	78.84 (4)
N2—Cr1—O3	96.78 (4)
O5—Cr1—O3	91.39 (4)
N1—Cr1—O1	79.13 (4)
N2—Cr1—O1	105.30 (4)
O5—Cr1—O1	93.27 (4)
O3—Cr1—O1	157.91 (4)
N1—Cr1—O7	96.08 (4)
N2—Cr1—O7	78.42 (4)
O5—Cr1—O7	157.76 (4)
O3—Cr1—O7	92.80 (4)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O11	0.83 (2)	2.08 (2)	2.8934 (16)	167.3 (19)
N4—H4B⋯O9	0.85 (2)	1.98 (2)	2.8343 (16)	178.5 (8)
O10—H10A⋯O15	0.91 (2)	1.63 (2)	2.5382 (15)	176 (2)
O14—H14B⋯O8	0.83 (2)	2.01 (2)	2.8255 (16)	169 (2)
O15—H15A⋯O14	0.86 (2)	1.82 (2)	2.6718 (17)	168 (2)
O16—H16A⋯O4	0.78 (2)	2.07 (2)	2.8006 (15)	156 (2)
O17—H17B⋯O3	0.79 (2)	1.99 (2)	2.7758 (14)	172 (2)
O18—H18A⋯O2	0.84 (2)	1.98 (2)	2.7927 (15)	162 (2)
O19—H19A⋯O6	0.85 (3)	1.95 (3)	2.7763 (15)	164 (2)
N5—H5A⋯O16i	0.85 (2)	1.87 (2)	2.7175 (16)	175 (2)
O12—H12A⋯O17ii	0.91 (2)	1.66 (3)	2.5720 (14)	176 (2)
O14—H14A⋯O18iii	0.79 (3)	1.98 (3)	2.7546 (17)	167 (2)
O15—H15B⋯O7iii	0.77 (2)	2.16 (2)	2.9105 (15)	162 (2)
O16—H16B⋯O9iv	0.83 (3)	2.05 (3)	2.8083 (15)	152 (2)
O17—H17A⋯O19v	0.85 (2)	1.84 (2)	2.6916 (16)	178 (2)
O18—H18B⋯O8vi	0.84 (3)	2.12 (3)	2.9558 (15)	171 (2)
O19—H19B⋯O13vii	0.81 (2)	2.17 (2)	2.9531 (16)	162 (2)
C5—H5⋯O7viii	0.94 (2)	2.392 (19)	3.251 (2)	152.2 (15)
C10—H10⋯O6ii	0.929 (19)	2.283 (19)	3.0919 (17)	145.4 (18)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) .