2,6-Diamino-pyridinium bis-(4-hydroxy-pyridine-2,6-dicarboxyl-ato-κO,N,O)chromate(III) dihydrate.

The reaction of chromium(III) nitrate hexa-hydrate, pyridine-2,6-diamine and 4-hydroxy-pyridine-2,6-dicarboxylic acid in a 1:2:2 molar ratio in aqueous solution resulted in the formation of the title compound, (C(5)H(8)N(3))[Cr(C(7)H(3)NO(5))(2)]·2H(2)O or (pydaH)[Cr(hypydc)(2)]·2H(2)O (where pyda is pyridine-2,6-diamine and hypydcH(2) is 4-hydroxy-pyridine-2,6-dicarboxylic acid). Each Cr(III )atom is hexa-coordinated by four O and two N atoms from two (hypydc)(2-) fragments, which act as tridentate ligands, in a distorted octa-hedral geometry. The O-Cr-O-C torsion angles between the two planes of the (hypydc)(2-) fragments [-99.81 (17) and 97.77 (17)°] indicate that these two units are almost perpendicular to one another. In the crystal structure, extensive O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds with D⋯A distances ranging from 2.560 (2) to 3.279 (3) Å, ion pairing, C-O⋯π [O⋯π = 3.166 (2) Å] and π-π stacking inter-actions between (hypydc)(2-) and (pydaH)(+) rings [with a centroid-centroid distance of 3.3353 (14) Å] contribute to the formation of a three-dimensional supra-molecular structure.

Related literature

For related literature, see: Aghabozorg et al., (2007 ▶); Aghabozorg, Manteghi et al. (2008 ▶); Aghabozorg, Saadaty et al. (2008 ▶); Ranjbar et al. (2001 ▶); Soleimannejad et al. (2008 ▶).

Experimental

Crystal data

(C5H8N3)[Cr(C7H3NO5)2]·2H2O

M = 560.38

Monoclinic,

a = 6.9590 (4) Å

b = 20.9904 (12) Å

c = 14.8951 (8) Å

β = 95.3030 (13)°

V = 2166.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.61 mm−1

T = 100 (2) K

0.32 × 0.08 × 0.07 mm

Data collection

Bruker APEXII CCD area-detector’ diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.829, T max = 0.959

24511 measured reflections

5229 independent reflections

3694 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.104

S = 1.02

5229 reflections

336 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.57 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808027347/ym2072sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027347/ym2072Isup2.hkl

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

(C5H8N3)[Cr(C7H3N1O5)2]·2H2O	F000 = 1148
Mr = 560.38	Dx = 1.718 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1320 reflections
a = 6.9590 (4) Å	θ = 3–28º
b = 20.9904 (12) Å	µ = 0.61 mm−1
c = 14.8951 (8) Å	T = 100 (2) K
β = 95.3030 (13)º	Needle, black
V = 2166.4 (2) Å3	0.32 × 0.08 × 0.07 mm
Z = 4

Bruker APEXII CCD area-detector' diffractometer	5229 independent reflections
Radiation source: fine-focus sealed tube	3694 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.078
T = 100(2) K	θmax = 28.0º
ω scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −9→9
Tmin = 0.829, Tmax = 0.959	k = −27→27
24511 measured reflections	l = −19→19

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.042	H-atom parameters constrained
wR(F2) = 0.104	w = 1/[σ2(Fo2) + (0.0468P)2 + 0.9675P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.002
5229 reflections	Δρmax = 0.47 e Å−3
336 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	0.46263 (6)	1.098248 (19)	0.20578 (3)	0.00992 (10)
O1	0.3226 (2)	1.01686 (8)	0.17083 (11)	0.0124 (4)
O2	0.1871 (3)	0.95887 (8)	0.05618 (11)	0.0141 (4)
O3	0.5836 (2)	1.18207 (8)	0.18501 (11)	0.0127 (4)
O4	0.6584 (3)	1.25241 (8)	0.08081 (12)	0.0154 (4)
O5	0.3766 (3)	1.11140 (8)	−0.20081 (11)	0.0166 (4)
H5O	0.4037	1.1423	−0.2284	0.020*
O6	0.7149 (2)	1.05418 (8)	0.23449 (11)	0.0138 (4)
O7	0.9177 (3)	1.01550 (9)	0.34882 (12)	0.0192 (4)
O8	0.2157 (2)	1.14101 (8)	0.23077 (11)	0.0135 (4)
O9	0.0389 (3)	1.17639 (9)	0.33928 (12)	0.0174 (4)
O10	0.5003 (3)	1.09070 (9)	0.61131 (11)	0.0190 (4)
H10O	0.6029	1.0846	0.6388	0.023*
O11	0.1788 (3)	0.93417 (8)	0.28815 (12)	0.0159 (4)
H11D	0.0901	0.9544	0.3071	0.019*
H11C	0.2300	0.9525	0.2480	0.046 (11)*
O12	0.4442 (3)	1.21870 (8)	−0.27326 (12)	0.0170 (4)
H12A	0.4497	1.2508	−0.2418	0.020*
H12B	0.3656	1.2273	−0.3160	0.020*
N1	0.4410 (3)	1.10250 (10)	0.07265 (13)	0.0106 (4)
N2	0.4719 (3)	1.09238 (9)	0.33828 (13)	0.0105 (4)
N3	−0.0320 (3)	1.16527 (10)	−0.07279 (13)	0.0117 (4)
H3NA	−0.0906	1.1294	−0.0859	0.014*
N4	−0.0433 (3)	1.19284 (11)	−0.22368 (14)	0.0178 (5)
H4NB	−0.0924	1.1563	−0.2413	0.021*
H4NA	−0.0025	1.2175	−0.2648	0.032 (9)*
N5	−0.0454 (3)	1.13054 (10)	0.07407 (14)	0.0135 (4)
H5NB	0.0119	1.1350	0.1281	0.016*
H5NA	−0.0986	1.0961	0.0506	0.016*
C1	0.3476 (3)	1.05598 (11)	0.02427 (16)	0.0101 (5)
C2	0.3233 (4)	1.05809 (12)	−0.06822 (16)	0.0117 (5)
H2A	0.2573	1.0250	−0.1019	0.014*
C3	0.3993 (3)	1.11092 (11)	−0.11176 (16)	0.0108 (5)
C4	0.4932 (3)	1.15980 (12)	−0.05965 (16)	0.0110 (5)
H4A	0.5443	1.1959	−0.0876	0.013*
C5	0.5088 (3)	1.15376 (11)	0.03232 (16)	0.0108 (5)
C6	0.2781 (3)	1.00555 (11)	0.08605 (16)	0.0105 (5)
C7	0.5931 (3)	1.20100 (12)	0.10225 (16)	0.0111 (5)
C8	0.6272 (4)	1.06604 (12)	0.38294 (16)	0.0123 (5)
C9	0.6455 (4)	1.06333 (12)	0.47589 (16)	0.0122 (5)
H9A	0.7555	1.0444	0.5078	0.015*
C10	0.4959 (4)	1.08960 (11)	0.52222 (16)	0.0137 (5)
C11	0.3335 (4)	1.11654 (12)	0.47336 (17)	0.0137 (5)
H11A	0.2305	1.1339	0.5032	0.016*
C12	0.3287 (4)	1.11698 (11)	0.38087 (16)	0.0117 (5)
C13	0.7689 (4)	1.04231 (12)	0.31917 (16)	0.0128 (5)
C14	0.1782 (4)	1.14746 (11)	0.31450 (16)	0.0118 (5)
C15	0.0192 (4)	1.20629 (12)	−0.13776 (17)	0.0132 (5)
C16	0.1308 (4)	1.25899 (12)	−0.11129 (17)	0.0149 (5)
H16A	0.1713	1.2879	−0.1549	0.018*
C17	0.1819 (4)	1.26871 (12)	−0.02048 (17)	0.0138 (5)
H17A	0.2600	1.3044	−0.0023	0.017*
C18	0.1230 (4)	1.22815 (12)	0.04490 (17)	0.0135 (5)
H18A	0.1551	1.2368	0.1071	0.016*
C19	0.0162 (4)	1.17463 (12)	0.01759 (16)	0.0122 (5)

	U11	U22	U33	U12	U13	U23
Cr1	0.0125 (2)	0.0104 (2)	0.00680 (19)	0.00029 (16)	0.00056 (14)	−0.00067 (15)
O1	0.0170 (9)	0.0115 (9)	0.0083 (9)	−0.0017 (7)	0.0000 (7)	0.0004 (6)
O2	0.0167 (9)	0.0123 (9)	0.0131 (9)	−0.0027 (7)	0.0006 (7)	−0.0010 (7)
O3	0.0161 (9)	0.0135 (9)	0.0084 (9)	−0.0023 (7)	0.0003 (7)	−0.0013 (7)
O4	0.0189 (10)	0.0120 (9)	0.0149 (10)	−0.0027 (8)	−0.0011 (7)	0.0010 (7)
O5	0.0284 (11)	0.0143 (10)	0.0068 (9)	−0.0023 (8)	0.0011 (7)	0.0021 (7)
O6	0.0143 (9)	0.0156 (9)	0.0114 (9)	0.0019 (7)	0.0014 (7)	−0.0015 (7)
O7	0.0170 (10)	0.0241 (11)	0.0161 (10)	0.0082 (8)	−0.0007 (7)	−0.0006 (8)
O8	0.0135 (9)	0.0175 (9)	0.0092 (9)	0.0023 (7)	−0.0002 (7)	−0.0007 (7)
O9	0.0177 (10)	0.0214 (10)	0.0134 (10)	0.0071 (8)	0.0029 (7)	−0.0001 (7)
O10	0.0214 (10)	0.0279 (11)	0.0073 (9)	0.0029 (8)	−0.0010 (7)	−0.0002 (7)
O11	0.0169 (10)	0.0181 (10)	0.0136 (9)	0.0020 (8)	0.0052 (7)	0.0022 (7)
O12	0.0230 (10)	0.0145 (9)	0.0128 (9)	−0.0013 (8)	−0.0018 (7)	0.0020 (7)
N1	0.0102 (10)	0.0101 (10)	0.0117 (10)	0.0019 (8)	0.0014 (8)	−0.0019 (8)
N2	0.0125 (10)	0.0100 (10)	0.0088 (10)	0.0002 (8)	0.0003 (8)	−0.0009 (8)
N3	0.0133 (11)	0.0102 (10)	0.0118 (11)	−0.0008 (8)	0.0018 (8)	0.0010 (8)
N4	0.0215 (12)	0.0190 (12)	0.0125 (11)	−0.0055 (10)	−0.0010 (9)	0.0041 (9)
N5	0.0147 (11)	0.0158 (11)	0.0097 (10)	−0.0018 (9)	−0.0007 (8)	−0.0002 (8)
C1	0.0092 (12)	0.0094 (12)	0.0118 (12)	0.0024 (9)	0.0024 (9)	−0.0006 (9)
C2	0.0116 (12)	0.0098 (12)	0.0132 (13)	0.0025 (9)	−0.0008 (9)	−0.0012 (9)
C3	0.0117 (12)	0.0140 (13)	0.0066 (11)	0.0042 (10)	0.0001 (9)	−0.0002 (9)
C4	0.0102 (12)	0.0115 (12)	0.0114 (12)	0.0030 (9)	0.0018 (9)	0.0018 (9)
C5	0.0081 (12)	0.0110 (12)	0.0134 (13)	0.0015 (9)	0.0017 (9)	−0.0007 (9)
C6	0.0103 (12)	0.0116 (12)	0.0099 (12)	0.0025 (10)	0.0030 (9)	0.0002 (9)
C7	0.0088 (12)	0.0133 (12)	0.0113 (12)	0.0031 (10)	0.0011 (9)	−0.0018 (9)
C8	0.0129 (13)	0.0105 (12)	0.0134 (13)	−0.0018 (10)	−0.0002 (10)	−0.0004 (9)
C9	0.0140 (13)	0.0112 (12)	0.0110 (12)	0.0022 (10)	−0.0014 (9)	0.0005 (9)
C10	0.0201 (13)	0.0110 (12)	0.0098 (12)	−0.0014 (10)	0.0008 (10)	0.0015 (9)
C11	0.0160 (13)	0.0123 (12)	0.0132 (13)	−0.0016 (10)	0.0037 (10)	−0.0013 (9)
C12	0.0122 (12)	0.0100 (12)	0.0124 (12)	−0.0020 (9)	−0.0011 (9)	−0.0021 (9)
C13	0.0154 (13)	0.0117 (12)	0.0113 (12)	−0.0009 (10)	0.0011 (10)	−0.0017 (9)
C14	0.0145 (13)	0.0109 (12)	0.0098 (12)	−0.0008 (10)	0.0005 (9)	0.0003 (9)
C15	0.0130 (13)	0.0143 (13)	0.0123 (13)	0.0050 (10)	0.0016 (10)	0.0030 (9)
C16	0.0150 (13)	0.0125 (13)	0.0173 (14)	0.0019 (10)	0.0030 (10)	0.0039 (10)
C17	0.0111 (12)	0.0088 (12)	0.0214 (14)	0.0015 (10)	0.0010 (10)	−0.0017 (10)
C18	0.0120 (13)	0.0130 (13)	0.0154 (13)	0.0014 (10)	0.0000 (10)	−0.0025 (10)
C19	0.0090 (12)	0.0152 (13)	0.0123 (13)	0.0034 (10)	−0.0001 (9)	−0.0002 (9)

Cr1—N2	1.973 (2)	N4—C15	1.343 (3)
Cr1—N1	1.977 (2)	N4—H4NB	0.8700
Cr1—O3	1.9872 (17)	N4—H4NA	0.8700
Cr1—O6	1.9957 (18)	N5—C19	1.347 (3)
Cr1—O8	2.0036 (17)	N5—H5NB	0.8700
Cr1—O1	2.0111 (17)	N5—H5NA	0.8701
O1—C6	1.294 (3)	C1—C2	1.373 (3)
O2—C6	1.227 (3)	C1—C6	1.511 (3)
O3—C7	1.303 (3)	C2—C3	1.412 (3)
O4—C7	1.225 (3)	C2—H2A	0.9500
O5—C3	1.321 (3)	C3—C4	1.410 (3)
O5—H5O	0.7999	C4—C5	1.370 (3)
O6—C13	1.306 (3)	C4—H4A	0.9500
O7—C13	1.225 (3)	C5—C7	1.516 (3)
O8—C14	1.305 (3)	C8—C9	1.380 (3)
O9—C14	1.229 (3)	C8—C13	1.515 (3)
O10—C10	1.325 (3)	C9—C10	1.413 (3)
O10—H10O	0.8000	C9—H9A	0.9500
O11—H11D	0.8199	C10—C11	1.405 (4)
O11—H11C	0.8201	C11—C12	1.375 (3)
O12—H12A	0.8198	C11—H11A	0.9500
O12—H12B	0.8201	C12—C14	1.514 (3)
N1—C5	1.339 (3)	C15—C16	1.388 (4)
N1—C1	1.345 (3)	C16—C17	1.382 (4)
N2—C12	1.334 (3)	C16—H16A	0.9500
N2—C8	1.335 (3)	C17—C18	1.384 (4)
N3—C15	1.367 (3)	C17—H17A	0.9500
N3—C19	1.371 (3)	C18—C19	1.387 (3)
N3—H3NA	0.8701	C18—H18A	0.9500
N2—Cr1—N1	177.33 (9)	C5—C4—H4A	120.9
N2—Cr1—O3	103.64 (8)	C3—C4—H4A	120.9
N1—Cr1—O3	78.35 (8)	N1—C5—C4	121.6 (2)
N2—Cr1—O6	79.04 (8)	N1—C5—C7	110.3 (2)
N1—Cr1—O6	102.70 (8)	C4—C5—C7	128.0 (2)
O3—Cr1—O6	93.82 (7)	O2—C6—O1	124.7 (2)
N2—Cr1—O8	77.96 (8)	O2—C6—C1	121.4 (2)
N1—Cr1—O8	100.31 (8)	O1—C6—C1	113.9 (2)
O3—Cr1—O8	90.88 (7)	O4—C7—O3	124.6 (2)
O6—Cr1—O8	156.99 (7)	O4—C7—C5	121.8 (2)
N2—Cr1—O1	100.15 (8)	O3—C7—C5	113.6 (2)
N1—Cr1—O1	77.79 (8)	N2—C8—C9	120.8 (2)
O3—Cr1—O1	156.06 (7)	N2—C8—C13	111.6 (2)
O6—Cr1—O1	93.28 (7)	C9—C8—C13	127.6 (2)
O8—Cr1—O1	91.46 (7)	C8—C9—C10	118.0 (2)
C6—O1—Cr1	118.37 (15)	C8—C9—H9A	121.0
C7—O3—Cr1	118.46 (15)	C10—C9—H9A	121.0
C3—O5—H5O	120.7	O10—C10—C11	117.1 (2)
C13—O6—Cr1	117.65 (15)	O10—C10—C9	123.1 (2)
C14—O8—Cr1	118.36 (15)	C11—C10—C9	119.8 (2)
C10—O10—H10O	116.5	C12—C11—C10	117.7 (2)
H11D—O11—H11C	113.6	C12—C11—H11A	121.1
H12A—O12—H12B	104.7	C10—C11—H11A	121.1
C5—N1—C1	121.1 (2)	N2—C12—C11	121.6 (2)
C5—N1—Cr1	119.27 (16)	N2—C12—C14	110.8 (2)
C1—N1—Cr1	119.54 (16)	C11—C12—C14	127.5 (2)
C12—N2—C8	121.9 (2)	O7—C13—O6	126.4 (2)
C12—N2—Cr1	119.67 (17)	O7—C13—C8	120.2 (2)
C8—N2—Cr1	118.33 (16)	O6—C13—C8	113.4 (2)
C15—N3—C19	123.3 (2)	O9—C14—O8	124.9 (2)
C15—N3—H3NA	122.3	O9—C14—C12	122.0 (2)
C19—N3—H3NA	114.3	O8—C14—C12	113.1 (2)
C15—N4—H4NB	123.8	N4—C15—N3	117.4 (2)
C15—N4—H4NA	116.6	N4—C15—C16	124.2 (2)
H4NB—N4—H4NA	117.1	N3—C15—C16	118.5 (2)
C19—N5—H5NB	111.0	C17—C16—C15	118.9 (2)
C19—N5—H5NA	117.8	C17—C16—H16A	120.6
H5NB—N5—H5NA	127.1	C15—C16—H16A	120.6
N1—C1—C2	121.5 (2)	C16—C17—C18	122.1 (2)
N1—C1—C6	110.4 (2)	C16—C17—H17A	118.9
C2—C1—C6	128.1 (2)	C18—C17—H17A	118.9
C1—C2—C3	118.0 (2)	C17—C18—C19	118.5 (2)
C1—C2—H2A	121.0	C17—C18—H18A	120.7
C3—C2—H2A	121.0	C19—C18—H18A	120.7
O5—C3—C4	123.6 (2)	N5—C19—N3	116.8 (2)
O5—C3—C2	116.9 (2)	N5—C19—C18	124.5 (2)
C4—C3—C2	119.5 (2)	N3—C19—C18	118.7 (2)
C5—C4—C3	118.2 (2)
N2—Cr1—O1—C6	175.80 (17)	C3—C4—C5—C7	−176.5 (2)
N1—Cr1—O1—C6	−2.46 (16)	Cr1—O1—C6—O2	−177.36 (19)
O3—Cr1—O1—C6	2.3 (3)	Cr1—O1—C6—C1	2.3 (3)
O6—Cr1—O1—C6	−104.75 (17)	N1—C1—C6—O2	179.2 (2)
O8—Cr1—O1—C6	97.77 (17)	C2—C1—C6—O2	−0.1 (4)
N2—Cr1—O3—C7	−177.73 (16)	N1—C1—C6—O1	−0.5 (3)
N1—Cr1—O3—C7	0.44 (17)	C2—C1—C6—O1	−179.8 (2)
O6—Cr1—O3—C7	102.64 (17)	Cr1—O3—C7—O4	177.52 (19)
O8—Cr1—O3—C7	−99.91 (17)	Cr1—O3—C7—C5	−0.6 (3)
O1—Cr1—O3—C7	−4.3 (3)	N1—C5—C7—O4	−177.7 (2)
N2—Cr1—O6—C13	−0.10 (17)	C4—C5—C7—O4	0.4 (4)
N1—Cr1—O6—C13	−178.02 (17)	N1—C5—C7—O3	0.5 (3)
O3—Cr1—O6—C13	103.07 (17)	C4—C5—C7—O3	178.6 (2)
O8—Cr1—O6—C13	1.7 (3)	C12—N2—C8—C9	−0.1 (4)
O1—Cr1—O6—C13	−99.81 (17)	Cr1—N2—C8—C9	176.98 (18)
N2—Cr1—O8—C14	2.31 (17)	C12—N2—C8—C13	−179.5 (2)
N1—Cr1—O8—C14	−179.77 (17)	Cr1—N2—C8—C13	−2.4 (3)
O3—Cr1—O8—C14	−101.46 (17)	N2—C8—C9—C10	−0.4 (4)
O6—Cr1—O8—C14	0.5 (3)	C13—C8—C9—C10	178.9 (2)
O1—Cr1—O8—C14	102.37 (17)	C8—C9—C10—O10	−178.7 (2)
O3—Cr1—N1—C5	−0.11 (17)	C8—C9—C10—C11	0.9 (4)
O6—Cr1—N1—C5	−91.45 (18)	O10—C10—C11—C12	178.6 (2)
O8—Cr1—N1—C5	88.65 (18)	C9—C10—C11—C12	−1.0 (4)
O1—Cr1—N1—C5	177.91 (19)	C8—N2—C12—C11	0.0 (4)
O3—Cr1—N1—C1	−175.84 (19)	Cr1—N2—C12—C11	−176.99 (18)
O6—Cr1—N1—C1	92.83 (18)	C8—N2—C12—C14	176.2 (2)
O8—Cr1—N1—C1	−87.08 (18)	Cr1—N2—C12—C14	−0.8 (3)
O1—Cr1—N1—C1	2.18 (17)	C10—C11—C12—N2	0.5 (4)
O3—Cr1—N2—C12	87.31 (19)	C10—C11—C12—C14	−175.0 (2)
O6—Cr1—N2—C12	178.62 (19)	Cr1—O6—C13—O7	179.5 (2)
O8—Cr1—N2—C12	−0.64 (18)	Cr1—O6—C13—C8	−1.1 (3)
O1—Cr1—N2—C12	−89.97 (19)	N2—C8—C13—O7	−178.4 (2)
O3—Cr1—N2—C8	−89.81 (18)	C9—C8—C13—O7	2.3 (4)
O6—Cr1—N2—C8	1.50 (18)	N2—C8—C13—O6	2.2 (3)
O8—Cr1—N2—C8	−177.77 (19)	C9—C8—C13—O6	−177.1 (2)
O1—Cr1—N2—C8	92.91 (18)	Cr1—O8—C14—O9	174.9 (2)
C5—N1—C1—C2	2.1 (3)	Cr1—O8—C14—C12	−3.3 (3)
Cr1—N1—C1—C2	177.73 (18)	N2—C12—C14—O9	−175.7 (2)
C5—N1—C1—C6	−177.3 (2)	C11—C12—C14—O9	0.2 (4)
Cr1—N1—C1—C6	−1.6 (3)	N2—C12—C14—O8	2.6 (3)
N1—C1—C2—C3	−0.1 (3)	C11—C12—C14—O8	178.5 (2)
C6—C1—C2—C3	179.1 (2)	C19—N3—C15—N4	−177.6 (2)
C1—C2—C3—O5	179.0 (2)	C19—N3—C15—C16	2.1 (4)
C1—C2—C3—C4	−1.2 (3)	N4—C15—C16—C17	178.2 (2)
O5—C3—C4—C5	−179.6 (2)	N3—C15—C16—C17	−1.5 (4)
C2—C3—C4—C5	0.6 (3)	C15—C16—C17—C18	−1.0 (4)
C1—N1—C5—C4	−2.7 (3)	C16—C17—C18—C19	2.8 (4)
Cr1—N1—C5—C4	−178.40 (18)	C15—N3—C19—N5	179.4 (2)
C1—N1—C5—C7	175.5 (2)	C15—N3—C19—C18	−0.3 (4)
Cr1—N1—C5—C7	−0.2 (3)	C17—C18—C19—N5	178.2 (2)
C3—C4—C5—N1	1.4 (4)	C17—C18—C19—N3	−2.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3NA···O2i	0.87	2.03	2.840 (3)	154
N4—H4NB···O11i	0.87	2.09	2.958 (3)	173
N4—H4NA···O3ii	0.87	2.33	3.122 (3)	151
N5—H5NB···O8	0.87	1.99	2.831 (3)	162
N5—H5NA···O2i	0.87	2.01	2.812 (3)	152
O5—H5O···O12	0.80	1.77	2.560 (2)	169
O10—H10O···O11iii	0.80	1.83	2.624 (3)	173
O11—H11C···O1	0.82	1.92	2.719 (2)	163
O11—H11D···O7iv	0.82	1.90	2.709 (3)	169
O12—H12A···O9v	0.82	2.01	2.809 (3)	165
O12—H12B···O4ii	0.82	2.05	2.872 (3)	177
C16—H16A···O3ii	0.95	2.49	3.265 (3)	139
C18—H18A···O12vi	0.95	2.59	3.279 (3)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3NA⋯O2i	0.87	2.03	2.840 (3)	154
N4—H4NB⋯O11i	0.87	2.09	2.958 (3)	173
N4—H4NA⋯O3ii	0.87	2.33	3.122 (3)	151
N5—H5NB⋯O8	0.87	1.99	2.831 (3)	162
N5—H5NA⋯O2i	0.87	2.01	2.812 (3)	152
O5—H5O⋯O12	0.80	1.77	2.560 (2)	169
O10—H10O⋯O11iii	0.80	1.83	2.624 (3)	173
O11—H11C⋯O1	0.82	1.92	2.719 (2)	163
O11—H11D⋯O7iv	0.82	1.90	2.709 (3)	169
O12—H12A⋯O9v	0.82	2.01	2.809 (3)	165
O12—H12B⋯O4ii	0.82	2.05	2.872 (3)	177
C16—H16A⋯O3ii	0.95	2.49	3.265 (3)	139
C18—H18A⋯O12vi	0.95	2.59	3.279 (3)	130

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