4-(4-Pyrid-yl)pyridinium bis-(pyridine-2,6-dicarboxyl-ato)chromium(III) tetra-hydrate.

The title compound, (C(10)H(9)N(2))[Cr(C(7)H(3)NO(4))(2)]·4H(2)O or (4,4'-bipyH)[Cr(pydc)(2)]·4H(2)O (where 4,4'-bipy is 4,4'-bipyridine and pydcH(2) is pyridine-2,6-dicarboxylic acid), was synthesized by the reaction of chromium(III) chloride hexa-hydrate with pyridine-2,6-dicarboxylic acid and 4,4'-bipyridine in a 1:2:4 molar ratio in aqueous solution. This compound is composed of an anionic complex, [Cr(pydc)(2)](-), protonated 4,4'-bipyridine as a counter-ion, (4,4'-bipyH)(+), and four uncoordinated water mol-ecules. The anion is a six-coordinate complex with a distorted octa-hedral geometry around the Cr(III) atom, formed by two tridentate pyridine-2,6-dicarboxyl-ate, pydc(2-), groups. Inter-molecular O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds, and C-O⋯π stacking inter-actions (with distances of 3.3390 (13) and 3.4575 (13) Å) connect the various components into a supra-molecular structure.

Related literature

For related literature, see: Aghabozorg, Attar Gharamaleki, Ghadermazi et al. (2007 ▶); Aghabozorg, Attar Gharamaleki, Ghasemikhah et al. (2007 ▶); Soleimannejad et al. (2007 ▶).

Experimental

Crystal data

(C10H9N2)[Cr(C7H3NO4)2]·4H2O

M = 611.46

Triclinic,

a = 9.3785 (19) Å

b = 9.4106 (19) Å

c = 14.542 (3) Å

α = 84.71 (3)°

β = 89.78 (3)°

γ = 87.25 (3)°

V = 1276.5 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.52 mm−1

T = 150 (2) K

0.32 × 0.28 × 0.16 mm

Data collection

Bruker SMART APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.851, T max = 0.921

31765 measured reflections

10833 independent reflections

8883 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.102

S = 1.05

10833 reflections

370 parameters

H-atom parameters constrained

Δρmax = 0.60 e Å−3

Δρmin = −0.57 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/S1600536808006594/om2216sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808006594/om2216Isup2.hkl

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

(C10H9N2)[Cr(C7H3NO4)2]·4H2O	Z = 2
Mr = 611.46	F000 = 630
Triclinic, P1	Dx = 1.591 Mg m−3
a = 9.3785 (19) Å	Mo Kα radiation λ = 0.71073 Å
b = 9.4106 (19) Å	Cell parameters from 12230 reflections
c = 14.542 (3) Å	θ = 2.2–35.8º
α = 84.71 (3)º	µ = 0.52 mm−1
β = 89.78 (3)º	T = 150 (2) K
γ = 87.25 (3)º	Block, purple
V = 1276.5 (4) Å3	0.32 × 0.28 × 0.16 mm

Bruker SMART APEXII diffractometer	10833 independent reflections
Radiation source: fine-focus sealed tube	8883 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.026
Detector resolution: 100 pixels mm-1	θmax = 36.1º
T = 150(2) K	θmin = 2.2º
ω scans	h = −14→15
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	k = −15→14
Tmin = 0.851, Tmax = 0.921	l = −23→24
31765 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038	H-atom parameters constrained
wR(F2) = 0.103	w = 1/[σ2(Fo2) + (0.048P)2 + 0.4592P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
10833 reflections	Δρmax = 0.60 e Å−3
370 parameters	Δρmin = −0.57 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.266361 (19)	0.491881 (19)	0.195816 (11)	0.01104 (4)
N1	0.26445 (10)	0.49786 (10)	0.05944 (6)	0.01197 (16)
N2	0.24857 (10)	0.48069 (10)	0.33175 (6)	0.01179 (15)
N3	0.72695 (12)	0.97534 (12)	0.45391 (7)	0.0194 (2)
N4	0.77831 (12)	0.99799 (11)	0.93219 (7)	0.01759 (19)
H4A	0.7795	0.9955	0.9926	0.021*
O1	0.12674 (9)	0.65329 (9)	0.16270 (5)	0.01546 (15)
O2	−0.00659 (10)	0.76524 (10)	0.04713 (6)	0.01965 (17)
O3	0.53501 (10)	0.23112 (10)	0.06204 (6)	0.01963 (17)
O4	0.41631 (9)	0.33790 (9)	0.17374 (5)	0.01495 (15)
O5	0.41777 (9)	0.62055 (9)	0.22808 (5)	0.01508 (15)
O6	0.52644 (10)	0.70866 (11)	0.34625 (6)	0.02158 (18)
O7	−0.04989 (10)	0.27542 (10)	0.32192 (6)	0.01938 (17)
O8	0.10916 (9)	0.35918 (9)	0.21729 (5)	0.01460 (15)
O9	−0.03988 (11)	0.69399 (11)	0.31867 (6)	0.0244 (2)
H9B	0.0051	0.6849	0.2685	0.029*
H9A	−0.1101	0.7519	0.3036	0.029*
O10	0.72454 (10)	0.88911 (10)	0.27755 (6)	0.01963 (17)
H10B	0.6586	0.8335	0.2943	0.024*
H10A	0.7280	0.9332	0.3259	0.024*
O11	0.75568 (11)	0.04005 (11)	0.11110 (6)	0.0244 (2)
H11A	0.7538	−0.0099	0.1628	0.029*
H11B	0.6918	0.1065	0.1146	0.029*
O12	0.62868 (11)	0.32459 (12)	0.32442 (7)	0.0285 (2)
H12B	0.5846	0.3188	0.2740	0.034*
H12A	0.7144	0.2935	0.3182	0.034*
C1	0.08705 (12)	0.67886 (12)	0.07649 (8)	0.01409 (18)
C2	0.17048 (12)	0.58722 (12)	0.01280 (7)	0.01299 (18)
C3	0.15612 (13)	0.58587 (13)	−0.08223 (8)	0.0166 (2)
H3	0.0898	0.6496	−0.1163	0.020*
C4	0.24262 (14)	0.48751 (14)	−0.12579 (8)	0.0186 (2)
H4	0.2348	0.4836	−0.1906	0.022*
C5	0.34043 (13)	0.39477 (13)	−0.07555 (8)	0.0168 (2)
H5	0.3998	0.3282	−0.1052	0.020*
C6	0.34819 (12)	0.40300 (12)	0.01900 (7)	0.01346 (18)
C7	0.44279 (12)	0.31500 (12)	0.08853 (8)	0.01428 (19)
C8	0.43694 (12)	0.63540 (12)	0.31482 (8)	0.01491 (19)
C9	0.33577 (12)	0.55471 (12)	0.37879 (7)	0.01382 (18)
C10	0.32408 (13)	0.55271 (13)	0.47402 (7)	0.0162 (2)
H10	0.3849	0.6063	0.5082	0.019*
C11	0.22016 (13)	0.46959 (13)	0.51800 (8)	0.0173 (2)
H11	0.2115	0.4642	0.5833	0.021*
C12	0.12876 (13)	0.39426 (12)	0.46697 (7)	0.01504 (19)
H12	0.0572	0.3383	0.4966	0.018*
C13	0.14545 (12)	0.40345 (12)	0.37187 (7)	0.01239 (18)
C14	0.05814 (12)	0.33886 (12)	0.30060 (7)	0.01412 (19)
C15	0.81914 (14)	1.05946 (15)	0.48966 (8)	0.0212 (2)
H15	0.8785	1.1144	0.4486	0.025*
C16	0.83252 (14)	1.07062 (14)	0.58368 (8)	0.0186 (2)
H16	0.9013	1.1295	0.6064	0.022*
C17	0.74259 (12)	0.99342 (12)	0.64399 (8)	0.01442 (19)
C18	0.75518 (12)	0.99884 (12)	0.74499 (7)	0.01396 (18)
C19	0.88777 (13)	0.97587 (12)	0.78816 (8)	0.01581 (19)
H19	0.9716	0.9624	0.7525	0.019*
C20	0.89631 (13)	0.97280 (13)	0.88267 (8)	0.0172 (2)
H20	0.9856	0.9529	0.9129	0.021*
C21	0.64985 (14)	1.02645 (14)	0.89264 (8)	0.0185 (2)
H21	0.5694	1.0483	0.9295	0.022*
C22	0.63443 (13)	1.02407 (13)	0.79875 (8)	0.0171 (2)
H22	0.5429	1.0394	0.7709	0.020*
C23	0.64325 (13)	0.90875 (13)	0.60749 (8)	0.0167 (2)
H23	0.5783	0.8573	0.6466	0.020*
C24	0.64132 (14)	0.90131 (13)	0.51256 (8)	0.0184 (2)
H24	0.5760	0.8407	0.4879	0.022*

	U11	U22	U33	U12	U13	U23
Cr1	0.01172 (8)	0.01332 (8)	0.00807 (7)	−0.00023 (6)	0.00025 (5)	−0.00118 (5)
N1	0.0121 (4)	0.0144 (4)	0.0094 (3)	−0.0014 (3)	0.0007 (3)	−0.0010 (3)
N2	0.0113 (4)	0.0139 (4)	0.0100 (3)	0.0002 (3)	−0.0004 (3)	−0.0007 (3)
N3	0.0213 (5)	0.0234 (5)	0.0134 (4)	0.0024 (4)	−0.0006 (4)	−0.0024 (4)
N4	0.0225 (5)	0.0186 (4)	0.0117 (4)	−0.0026 (4)	−0.0007 (3)	−0.0005 (3)
O1	0.0172 (4)	0.0169 (4)	0.0119 (3)	0.0024 (3)	0.0004 (3)	−0.0012 (3)
O2	0.0185 (4)	0.0182 (4)	0.0211 (4)	0.0032 (3)	−0.0019 (3)	0.0021 (3)
O3	0.0178 (4)	0.0206 (4)	0.0205 (4)	0.0040 (3)	0.0026 (3)	−0.0046 (3)
O4	0.0155 (4)	0.0170 (4)	0.0121 (3)	0.0017 (3)	−0.0003 (3)	−0.0014 (3)
O5	0.0164 (4)	0.0182 (4)	0.0109 (3)	−0.0033 (3)	0.0015 (3)	−0.0017 (3)
O6	0.0212 (4)	0.0266 (5)	0.0181 (4)	−0.0094 (4)	−0.0012 (3)	−0.0044 (3)
O7	0.0160 (4)	0.0223 (4)	0.0201 (4)	−0.0059 (3)	0.0019 (3)	−0.0010 (3)
O8	0.0150 (4)	0.0178 (4)	0.0111 (3)	−0.0026 (3)	−0.0003 (3)	−0.0012 (3)
O9	0.0235 (5)	0.0309 (5)	0.0172 (4)	0.0059 (4)	0.0060 (3)	0.0019 (4)
O10	0.0213 (4)	0.0245 (4)	0.0133 (3)	−0.0037 (3)	0.0023 (3)	−0.0016 (3)
O11	0.0264 (5)	0.0310 (5)	0.0137 (4)	0.0105 (4)	0.0033 (3)	0.0021 (3)
O12	0.0237 (5)	0.0425 (6)	0.0191 (4)	−0.0003 (4)	−0.0029 (4)	−0.0023 (4)
C1	0.0135 (5)	0.0144 (4)	0.0142 (4)	−0.0015 (4)	0.0007 (4)	0.0000 (4)
C2	0.0126 (4)	0.0149 (4)	0.0112 (4)	−0.0021 (4)	−0.0005 (3)	0.0007 (3)
C3	0.0174 (5)	0.0208 (5)	0.0116 (4)	−0.0040 (4)	−0.0022 (4)	0.0014 (4)
C4	0.0218 (6)	0.0248 (6)	0.0098 (4)	−0.0059 (5)	−0.0001 (4)	−0.0024 (4)
C5	0.0181 (5)	0.0212 (5)	0.0120 (4)	−0.0043 (4)	0.0030 (4)	−0.0047 (4)
C6	0.0134 (5)	0.0160 (5)	0.0114 (4)	−0.0019 (4)	0.0021 (3)	−0.0026 (3)
C7	0.0137 (5)	0.0149 (4)	0.0145 (4)	−0.0015 (4)	0.0004 (4)	−0.0025 (4)
C8	0.0150 (5)	0.0171 (5)	0.0129 (4)	−0.0010 (4)	0.0003 (4)	−0.0026 (4)
C9	0.0136 (5)	0.0169 (5)	0.0110 (4)	−0.0003 (4)	−0.0001 (3)	−0.0022 (3)
C10	0.0175 (5)	0.0208 (5)	0.0107 (4)	0.0001 (4)	−0.0012 (4)	−0.0033 (4)
C11	0.0194 (5)	0.0227 (5)	0.0095 (4)	0.0016 (4)	0.0005 (4)	−0.0014 (4)
C12	0.0154 (5)	0.0177 (5)	0.0115 (4)	0.0009 (4)	0.0019 (4)	0.0012 (4)
C13	0.0110 (4)	0.0148 (4)	0.0112 (4)	0.0010 (4)	0.0000 (3)	−0.0006 (3)
C14	0.0137 (5)	0.0152 (4)	0.0133 (4)	0.0001 (4)	0.0000 (3)	−0.0007 (4)
C15	0.0224 (6)	0.0262 (6)	0.0146 (5)	−0.0027 (5)	0.0020 (4)	0.0009 (4)
C16	0.0191 (5)	0.0216 (5)	0.0152 (4)	−0.0043 (4)	0.0003 (4)	−0.0005 (4)
C17	0.0142 (5)	0.0158 (5)	0.0132 (4)	0.0008 (4)	−0.0003 (3)	−0.0014 (4)
C18	0.0157 (5)	0.0131 (4)	0.0131 (4)	−0.0009 (4)	0.0000 (4)	−0.0014 (3)
C19	0.0151 (5)	0.0166 (5)	0.0157 (4)	0.0007 (4)	−0.0006 (4)	−0.0026 (4)
C20	0.0189 (5)	0.0170 (5)	0.0155 (4)	0.0005 (4)	−0.0029 (4)	−0.0007 (4)
C21	0.0189 (5)	0.0216 (5)	0.0153 (4)	−0.0027 (4)	0.0035 (4)	−0.0020 (4)
C22	0.0149 (5)	0.0207 (5)	0.0155 (4)	0.0002 (4)	0.0005 (4)	−0.0012 (4)
C23	0.0167 (5)	0.0185 (5)	0.0149 (4)	−0.0016 (4)	−0.0001 (4)	−0.0014 (4)
C24	0.0194 (5)	0.0199 (5)	0.0162 (5)	0.0002 (4)	−0.0028 (4)	−0.0037 (4)

Cr1—N2	1.9767 (10)	C3—C4	1.3958 (18)
Cr1—N1	1.9789 (10)	C3—H3	0.9500
Cr1—O8	1.9829 (10)	C4—C5	1.3956 (18)
Cr1—O1	1.9832 (11)	C4—H4	0.9500
Cr1—O5	1.9944 (10)	C5—C6	1.3865 (15)
Cr1—O4	2.0168 (10)	C5—H5	0.9500
N1—C2	1.3312 (15)	C6—C7	1.5091 (17)
N1—C6	1.3362 (15)	C8—C9	1.5080 (17)
N2—C9	1.3300 (15)	C9—C10	1.3872 (15)
N2—C13	1.3375 (15)	C10—C11	1.3953 (18)
N3—C15	1.3378 (18)	C10—H10	0.9500
N3—C24	1.3403 (17)	C11—C12	1.3958 (18)
N4—C21	1.3416 (17)	C11—H11	0.9500
N4—C20	1.3415 (17)	C12—C13	1.3864 (15)
N4—H4A	0.8760	C12—H12	0.9500
O1—C1	1.3067 (14)	C13—C14	1.5116 (16)
O2—C1	1.2185 (15)	C15—C16	1.3874 (17)
O3—C7	1.2278 (14)	C15—H15	0.9500
O4—C7	1.2982 (14)	C16—C17	1.3942 (17)
O5—C8	1.2960 (13)	C16—H16	0.9500
O6—C8	1.2270 (15)	C17—C23	1.3920 (17)
O7—C14	1.2250 (15)	C17—C18	1.4797 (16)
O8—C14	1.3018 (14)	C18—C19	1.3937 (17)
O9—H9B	0.8500	C18—C22	1.3970 (17)
O9—H9A	0.8500	C19—C20	1.3745 (16)
O10—H10B	0.8500	C19—H19	0.9500
O10—H10A	0.8499	C20—H20	0.9500
O11—H11A	0.8499	C21—C22	1.3759 (17)
O11—H11B	0.8500	C21—H21	0.9500
O12—H12B	0.8501	C22—H22	0.9500
O12—H12A	0.8500	C23—C24	1.3889 (16)
C1—C2	1.5136 (16)	C23—H23	0.9500
C2—C3	1.3902 (15)	C24—H24	0.9500
N2—Cr1—N1	174.39 (4)	O4—C7—C6	114.16 (10)
N2—Cr1—O8	78.67 (5)	O6—C8—O5	125.61 (11)
N1—Cr1—O8	96.21 (5)	O6—C8—C9	120.11 (10)
N2—Cr1—O1	99.21 (5)	O5—C8—C9	114.27 (10)
N1—Cr1—O1	78.40 (5)	N2—C9—C10	120.34 (11)
O8—Cr1—O1	90.66 (4)	N2—C9—C8	110.97 (9)
N2—Cr1—O5	78.69 (5)	C10—C9—C8	128.67 (11)
N1—Cr1—O5	106.41 (5)	C9—C10—C11	117.90 (11)
O8—Cr1—O5	157.36 (3)	C9—C10—H10	121.0
O1—Cr1—O5	93.07 (4)	C11—C10—H10	121.0
N2—Cr1—O4	103.97 (5)	C10—C11—C12	120.65 (10)
N1—Cr1—O4	78.62 (5)	C10—C11—H11	119.7
O8—Cr1—O4	94.98 (4)	C12—C11—H11	119.7
O1—Cr1—O4	156.79 (4)	C13—C12—C11	118.07 (11)
O5—Cr1—O4	90.33 (4)	C13—C12—H12	121.0
C2—N1—C6	122.82 (9)	C11—C12—H12	121.0
C2—N1—Cr1	118.44 (8)	N2—C13—C12	120.02 (10)
C6—N1—Cr1	118.44 (8)	N2—C13—C14	111.00 (9)
C9—N2—C13	122.97 (9)	C12—C13—C14	128.97 (10)
C9—N2—Cr1	118.61 (8)	O7—C14—O8	125.24 (11)
C13—N2—Cr1	118.36 (8)	O7—C14—C13	121.47 (10)
C15—N3—C24	117.64 (11)	O8—C14—C13	113.29 (10)
C21—N4—C20	122.19 (10)	N3—C15—C16	123.38 (12)
C21—N4—H4A	115.4	N3—C15—H15	118.3
C20—N4—H4A	122.4	C16—C15—H15	118.3
C1—O1—Cr1	118.47 (8)	C15—C16—C17	118.44 (12)
C7—O4—Cr1	117.10 (8)	C15—C16—H16	120.8
C8—O5—Cr1	117.43 (8)	C17—C16—H16	120.8
C14—O8—Cr1	118.01 (8)	C23—C17—C16	118.75 (11)
H9B—O9—H9A	104.8	C23—C17—C18	120.75 (11)
H10B—O10—H10A	98.4	C16—C17—C18	120.49 (11)
H11A—O11—H11B	105.5	C19—C18—C22	118.99 (10)
H12B—O12—H12A	108.4	C19—C18—C17	120.31 (11)
O2—C1—O1	125.94 (11)	C22—C18—C17	120.69 (11)
O2—C1—C2	121.35 (10)	C20—C19—C18	119.52 (11)
O1—C1—C2	112.71 (10)	C20—C19—H19	120.2
N1—C2—C3	120.49 (11)	C18—C19—H19	120.2
N1—C2—C1	111.40 (9)	N4—C20—C19	119.90 (11)
C3—C2—C1	128.08 (10)	N4—C20—H20	120.0
C2—C3—C4	117.57 (11)	C19—C20—H20	120.0
C2—C3—H3	121.2	N4—C21—C22	120.15 (11)
C4—C3—H3	121.2	N4—C21—H21	119.9
C5—C4—C3	121.00 (10)	C22—C21—H21	119.9
C5—C4—H4	119.5	C21—C22—C18	119.12 (11)
C3—C4—H4	119.5	C21—C22—H22	120.4
C6—C5—C4	117.84 (11)	C18—C22—H22	120.4
C6—C5—H5	121.1	C24—C23—C17	118.39 (11)
C4—C5—H5	121.1	C24—C23—H23	120.8
N1—C6—C5	120.28 (11)	C17—C23—H23	120.8
N1—C6—C7	111.37 (9)	N3—C24—C23	123.35 (12)
C5—C6—C7	128.35 (10)	N3—C24—H24	118.3
O3—C7—O4	126.02 (11)	C23—C24—H24	118.3
O3—C7—C6	119.82 (10)
N2—Cr1—N1—C2	59.1 (4)	C2—N1—C6—C7	−179.40 (10)
O8—Cr1—N1—C2	83.23 (9)	Cr1—N1—C6—C7	−5.76 (12)
O1—Cr1—N1—C2	−6.16 (8)	C4—C5—C6—N1	−0.36 (17)
O5—Cr1—N1—C2	−95.97 (9)	C4—C5—C6—C7	179.39 (11)
O4—Cr1—N1—C2	177.08 (9)	Cr1—O4—C7—O3	176.09 (10)
N2—Cr1—N1—C6	−114.8 (4)	Cr1—O4—C7—C6	−3.77 (12)
O8—Cr1—N1—C6	−90.69 (9)	N1—C6—C7—O3	−173.79 (11)
O1—Cr1—N1—C6	179.91 (9)	C5—C6—C7—O3	6.45 (19)
O5—Cr1—N1—C6	90.11 (9)	N1—C6—C7—O4	6.08 (14)
O4—Cr1—N1—C6	3.16 (8)	C5—C6—C7—O4	−173.68 (11)
N1—Cr1—N2—C9	−156.0 (4)	Cr1—O5—C8—O6	178.97 (10)
O8—Cr1—N2—C9	179.56 (9)	Cr1—O5—C8—C9	−1.96 (13)
O1—Cr1—N2—C9	−91.62 (9)	C13—N2—C9—C10	1.01 (17)
O5—Cr1—N2—C9	−0.31 (8)	Cr1—N2—C9—C10	178.25 (8)
O4—Cr1—N2—C9	87.19 (9)	C13—N2—C9—C8	−177.80 (10)
N1—Cr1—N2—C13	21.4 (4)	Cr1—N2—C9—C8	−0.56 (12)
O8—Cr1—N2—C13	−3.07 (8)	O6—C8—C9—N2	−179.25 (11)
O1—Cr1—N2—C13	85.75 (9)	O5—C8—C9—N2	1.62 (14)
O5—Cr1—N2—C13	177.06 (9)	O6—C8—C9—C10	2.06 (19)
O4—Cr1—N2—C13	−95.44 (9)	O5—C8—C9—C10	−177.07 (11)
N2—Cr1—O1—C1	−167.76 (8)	N2—C9—C10—C11	0.90 (17)
N1—Cr1—O1—C1	7.07 (8)	C8—C9—C10—C11	179.49 (11)
O8—Cr1—O1—C1	−89.13 (9)	C9—C10—C11—C12	−1.70 (18)
O5—Cr1—O1—C1	113.21 (9)	C10—C11—C12—C13	0.66 (17)
O4—Cr1—O1—C1	15.18 (15)	C9—N2—C13—C12	−2.11 (17)
N2—Cr1—O4—C7	175.52 (8)	Cr1—N2—C13—C12	−179.36 (8)
N1—Cr1—O4—C7	0.63 (8)	C9—N2—C13—C14	176.49 (10)
O8—Cr1—O4—C7	95.98 (9)	Cr1—N2—C13—C14	−0.76 (12)
O1—Cr1—O4—C7	−7.47 (14)	C11—C12—C13—N2	1.23 (16)
O5—Cr1—O4—C7	−106.05 (9)	C11—C12—C13—C14	−177.09 (11)
N2—Cr1—O5—C8	1.31 (8)	Cr1—O8—C14—O7	170.02 (9)
N1—Cr1—O5—C8	178.90 (8)	Cr1—O8—C14—C13	−9.45 (12)
O8—Cr1—O5—C8	0.96 (15)	N2—C13—C14—O7	−173.01 (11)
O1—Cr1—O5—C8	100.09 (9)	C12—C13—C14—O7	5.43 (19)
O4—Cr1—O5—C8	−102.88 (9)	N2—C13—C14—O8	6.48 (14)
N2—Cr1—O8—C14	7.16 (8)	C12—C13—C14—O8	−175.08 (11)
N1—Cr1—O8—C14	−170.50 (8)	C24—N3—C15—C16	1.7 (2)
O1—Cr1—O8—C14	−92.10 (9)	N3—C15—C16—C17	−1.9 (2)
O5—Cr1—O8—C14	7.50 (15)	C15—C16—C17—C23	−0.10 (18)
O4—Cr1—O8—C14	110.44 (9)	C15—C16—C17—C18	178.42 (11)
Cr1—O1—C1—O2	173.01 (10)	C23—C17—C18—C19	128.56 (12)
Cr1—O1—C1—C2	−6.65 (12)	C16—C17—C18—C19	−49.93 (16)
C6—N1—C2—C3	−0.41 (17)	C23—C17—C18—C22	−50.12 (16)
Cr1—N1—C2—C3	−174.05 (8)	C16—C17—C18—C22	131.39 (13)
C6—N1—C2—C1	178.07 (10)	C22—C18—C19—C20	2.58 (17)
Cr1—N1—C2—C1	4.43 (12)	C17—C18—C19—C20	−176.12 (11)
O2—C1—C2—N1	−178.27 (11)	C21—N4—C20—C19	0.06 (18)
O1—C1—C2—N1	1.41 (14)	C18—C19—C20—N4	−2.87 (18)
O2—C1—C2—C3	0.07 (18)	C20—N4—C21—C22	3.03 (18)
O1—C1—C2—C3	179.74 (11)	N4—C21—C22—C18	−3.20 (18)
N1—C2—C3—C4	0.40 (17)	C19—C18—C22—C21	0.42 (17)
C1—C2—C3—C4	−177.80 (11)	C17—C18—C22—C21	179.12 (11)
C2—C3—C4—C5	−0.40 (18)	C16—C17—C23—C24	2.07 (17)
C3—C4—C5—C6	0.38 (18)	C18—C17—C23—C24	−176.44 (11)
C2—N1—C6—C5	0.39 (17)	C15—N3—C24—C23	0.49 (19)
Cr1—N1—C6—C5	174.03 (9)	C17—C23—C24—N3	−2.37 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O11i	0.88	1.82	2.6736 (14)	164
O9—H9B···O1	0.85	1.95	2.7944 (15)	173
O9—H9A···O10ii	0.85	1.98	2.8336 (16)	176
O10—H10B···O6	0.85	1.86	2.7035 (16)	172
O10—H10A···N3	0.85	1.94	2.7610 (15)	162
O11—H11A···O10iii	0.85	1.87	2.7132 (15)	172
O11—H11B···O3	0.85	1.95	2.7282 (16)	152
O12—H12B···O4	0.85	2.14	2.9569 (16)	160
O12—H12A···O7iv	0.85	2.21	3.0284 (16)	162
C3—H3···O8v	0.95	2.39	3.1688 (16)	139
C5—H5···O5vi	0.95	2.50	3.1737 (16)	128
C10—H10···O12vii	0.95	2.58	3.2867 (16)	132
C11—H11···O9viii	0.95	2.58	3.2271 (17)	126
C15—H15···O7ix	0.95	2.39	3.3002 (17)	160
C16—H16···O9x	0.95	2.49	3.4235 (18)	169
C20—H20···O2xi	0.95	2.51	3.0576 (16)	117
C20—H20···O11xii	0.95	2.45	3.2615 (17)	143
C24—H24···O6	0.95	2.56	3.3634 (17)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O11i	0.88	1.82	2.6736 (14)	164
O9—H9B⋯O1	0.85	1.95	2.7944 (15)	173
O9—H9A⋯O10ii	0.85	1.98	2.8336 (16)	176
O10—H10B⋯O6	0.85	1.86	2.7035 (16)	172
O10—H10A⋯N3	0.85	1.94	2.7610 (15)	162
O11—H11A⋯O10iii	0.85	1.87	2.7132 (15)	172
O11—H11B⋯O3	0.85	1.95	2.7282 (16)	152
O12—H12B⋯O4	0.85	2.14	2.9569 (16)	160
O12—H12A⋯O7iv	0.85	2.21	3.0284 (16)	162
C3—H3⋯O8v	0.95	2.39	3.1688 (16)	139
C5—H5⋯O5vi	0.95	2.50	3.1737 (16)	128
C10—H10⋯O12vii	0.95	2.58	3.2867 (16)	132
C11—H11⋯O9viii	0.95	2.58	3.2271 (17)	126
C15—H15⋯O7ix	0.95	2.39	3.3002 (17)	160
C16—H16⋯O9x	0.95	2.49	3.4235 (18)	169
C20—H20⋯O2xi	0.95	2.51	3.0576 (16)	117
C20—H20⋯O11xii	0.95	2.45	3.2615 (17)	143
C24—H24⋯O6	0.95	2.56	3.3634 (17)	143

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) ; (ix) ; (x) ; (xi) ; (xii) .