Diaqua-bis(ciprofloxacinato)manganese(II) 2,2'-bipyridine solvate tetrahydrate.

In the crystal structure of the title compound {systematic name: diaquabis-[1-cyclo-propyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-quinoline-3-carboxyl-ato]manganese(II) 2,2'-bi-pyridine solvate tetrahydrate}, [Mn(C(17)H(17)FN(3)O(3))(2)(H(2)O)(2)]·C(10)H(8)N(2)·4H(2)O, the pyridone O and one carboxyl-ate O atom of the two ciprofloxacin ligands are bound to the Mn(II) ion and occupy the equatorial positions, while the two aqua O atoms lie in the apical positions resulting in a distorted octa-hedral geometry. The crystal packing is stabilized by N-H⋯O and O-H⋯O hydrogen bonding interactions.

Related literature

Manganese is a cofactor or required metal ion for many enzymes, such as superoxide dismutase, glutamine synthetase and arginase, see: Dukhande et al. (2006 ▶).

Experimental

Crystal data

[Mn(C17H17FN3O3)2(H2O)2]·C10H8N2·4H2O

M = 979.89

Triclinic,

a = 10.0355 (3) Å

b = 11.1409 (3) Å

c = 11.8461 (3) Å

α = 66.905 (2)°

β = 68.933 (2)°

γ = 85.858 (2)°

V = 1133.22 (6) Å3

Z = 1

Mo Kα radiation

μ = 0.37 mm−1

T = 296 K

0.42 × 0.17 × 0.05 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.926, T max = 0.983

14989 measured reflections

5061 independent reflections

3310 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.084

wR(F 2) = 0.274

S = 1.08

5061 reflections

313 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.07 e Å−3

Δρmin = −0.65 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809021783/at2799sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809021783/at2799Isup2.hkl

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

[Mn(C17H17FN3O3)2(H2O)2]·C10H8N2·4H2O	Z = 1
Mr = 979.89	F(000) = 513
Triclinic, P1	Dx = 1.436 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.0355 (3) Å	Cell parameters from 2729 reflections
b = 11.1409 (3) Å	θ = 2.0–27.6°
c = 11.8461 (3) Å	µ = 0.37 mm−1
α = 66.905 (2)°	T = 296 K
β = 68.933 (2)°	Sheet, yellow
γ = 85.858 (2)°	0.42 × 0.17 × 0.05 mm
V = 1133.22 (6) Å3

Bruker APEXII CCD area-detector diffractometer	5061 independent reflections
Radiation source: fine-focus sealed tube	3310 reflections with I > 2σ(I)
graphite	Rint = 0.042
φ and ω scans	θmax = 27.6°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→12
Tmin = 0.926, Tmax = 0.983	k = −14→14
14989 measured reflections	l = −15→15

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)] = 0.084	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.274	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.1334P)2 + 2.3765P] where P = (Fo2 + 2Fc2)/3
5061 reflections	(Δ/σ)max < 0.001
313 parameters	Δρmax = 1.07 e Å−3
6 restraints	Δρmin = −0.65 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
Mn1	0.0000	−0.5000	0.5000	0.0346 (3)
F1	0.4111 (3)	−0.0038 (3)	−0.0828 (3)	0.0517 (9)
N1	−0.1402 (4)	0.0159 (4)	0.2298 (4)	0.0313 (9)
N2	0.3086 (4)	0.2389 (4)	−0.1295 (4)	0.0355 (9)
N3	0.4635 (4)	0.4907 (4)	−0.2699 (4)	0.0406 (10)
H3B	0.4905	0.5657	−0.2771	0.049*
N4	0.1028 (5)	0.1554 (4)	0.3907 (5)	0.0447 (11)
O1	0.0631 (4)	−0.3212 (3)	0.3262 (3)	0.0409 (9)
O1W	−0.0267 (5)	−0.6032 (4)	0.3810 (4)	0.0494 (10)
H1WA	0.004 (7)	−0.678 (3)	0.384 (6)	0.074*
H1WB	−0.004 (8)	−0.564 (5)	0.297 (2)	0.074*
O2	−0.2083 (4)	−0.4338 (3)	0.5255 (4)	0.0457 (9)
O2W	0.3929 (3)	0.5957 (3)	−0.0476 (3)	0.0237 (6)
H2WB	0.4451	0.5947	−0.0045	0.028*
H2WA	0.445 (4)	0.601 (5)	−0.115 (2)	0.036*
O3	−0.3858 (4)	−0.3070 (3)	0.5148 (4)	0.0490 (10)
O3W	0.0870 (3)	−0.4804 (3)	0.0850 (3)	0.0279 (7)
H3WA	0.0654	−0.4915	0.0265	0.034*
H3WB	0.1756	−0.4736	0.0723	0.034*
C1	−0.2563 (5)	−0.3264 (4)	0.4764 (5)	0.0339 (11)
C2	−0.1559 (5)	−0.2151 (4)	0.3635 (5)	0.0313 (10)
C3	−0.2132 (5)	−0.0963 (4)	0.3248 (5)	0.0328 (10)
H3A	−0.3104	−0.0935	0.3682	0.039*
C4	−0.2122 (5)	0.1368 (4)	0.2043 (5)	0.0344 (11)
H4A	−0.2336	0.1699	0.1234	0.041*
C5	−0.3182 (6)	0.1616 (5)	0.3180 (5)	0.0434 (13)
H5A	−0.4015	0.2067	0.3057	0.052*
H5B	−0.3349	0.0959	0.4058	0.052*
C6	−0.1751 (6)	0.2373 (5)	0.2431 (5)	0.0423 (12)
H6A	−0.1718	0.3285	0.1859	0.051*
H6B	−0.1053	0.2178	0.2859	0.051*
C7	0.0015 (5)	0.0152 (4)	0.1534 (4)	0.0294 (10)
C8	0.0804 (5)	0.1295 (4)	0.0504 (5)	0.0313 (10)
H8A	0.0372	0.2081	0.0333	0.038*
C9	0.2217 (5)	0.1273 (4)	−0.0263 (4)	0.0307 (10)
C10	0.2348 (5)	0.3576 (4)	−0.1651 (5)	0.0358 (11)
H10A	0.2045	0.3884	−0.0943	0.043*
H10B	0.1503	0.3394	−0.1792	0.043*
C11	0.3359 (6)	0.4625 (5)	−0.2906 (5)	0.0388 (12)
H11A	0.3639	0.4324	−0.3618	0.047*
H11B	0.2872	0.5417	−0.3151	0.047*
C12	0.5392 (6)	0.3696 (5)	−0.2344 (6)	0.0509 (15)
H12A	0.6238	0.3877	−0.2204	0.061*
H12B	0.5693	0.3391	−0.3054	0.061*
C13	0.4387 (6)	0.2654 (5)	−0.1099 (6)	0.0473 (14)
H13A	0.4868	0.1857	−0.0864	0.057*
H13B	0.4124	0.2947	−0.0382	0.057*
C14	0.2779 (5)	0.0040 (5)	−0.0004 (5)	0.0352 (11)
C15	0.2065 (5)	−0.1080 (4)	0.1001 (5)	0.0333 (10)
H15A	0.2499	−0.1866	0.1140	0.040*
C16	0.0660 (5)	−0.1043 (4)	0.1832 (4)	0.0279 (9)
C17	−0.0088 (5)	−0.2225 (4)	0.2956 (4)	0.0295 (10)
C18	0.2345 (7)	0.2003 (6)	0.3002 (6)	0.0550 (15)
H18A	0.2567	0.2904	0.2604	0.066*
C19	0.3394 (7)	0.1219 (7)	0.2622 (6)	0.0551 (15)
H19A	0.4289	0.1577	0.1983	0.066*
C20	0.3059 (7)	−0.0116 (6)	0.3230 (6)	0.0551 (15)
H20A	0.3739	−0.0680	0.3012	0.066*
C21	0.1722 (6)	−0.0612 (6)	0.4157 (6)	0.0476 (13)
H21A	0.1483	−0.1510	0.4553	0.057*
C22	0.0728 (5)	0.0237 (5)	0.4498 (5)	0.0366 (11)

	U11	U22	U33	U12	U13	U23
Mn1	0.0330 (6)	0.0237 (5)	0.0326 (6)	−0.0009 (4)	−0.0045 (4)	−0.0028 (4)
F1	0.0347 (16)	0.0388 (17)	0.0486 (19)	0.0009 (13)	0.0122 (14)	−0.0083 (14)
N1	0.030 (2)	0.0248 (19)	0.028 (2)	0.0007 (15)	−0.0033 (16)	−0.0060 (16)
N2	0.032 (2)	0.027 (2)	0.032 (2)	−0.0046 (16)	−0.0048 (17)	−0.0012 (16)
N3	0.037 (2)	0.028 (2)	0.037 (2)	−0.0093 (17)	−0.0032 (19)	−0.0006 (18)
N4	0.043 (3)	0.041 (2)	0.041 (3)	−0.002 (2)	−0.006 (2)	−0.014 (2)
O1	0.0350 (19)	0.0264 (17)	0.038 (2)	0.0038 (14)	−0.0008 (15)	−0.0011 (14)
O1W	0.067 (3)	0.037 (2)	0.040 (2)	0.0014 (19)	−0.015 (2)	−0.0137 (17)
O2	0.0339 (19)	0.0291 (18)	0.046 (2)	−0.0016 (14)	−0.0031 (16)	0.0034 (15)
O2W	0.0189 (15)	0.0200 (14)	0.0395 (18)	0.0028 (11)	−0.0226 (13)	−0.0083 (13)
O3	0.0268 (19)	0.0349 (19)	0.053 (2)	−0.0019 (14)	0.0021 (16)	0.0004 (17)
O3W	0.0267 (16)	0.0398 (17)	0.0179 (15)	0.0073 (13)	−0.0140 (12)	−0.0074 (13)
C1	0.033 (3)	0.028 (2)	0.028 (2)	−0.0028 (19)	−0.002 (2)	−0.0058 (19)
C2	0.032 (2)	0.028 (2)	0.027 (2)	−0.0037 (18)	−0.0071 (19)	−0.0057 (18)
C3	0.025 (2)	0.029 (2)	0.030 (2)	−0.0051 (18)	−0.0009 (19)	−0.0032 (19)
C4	0.032 (3)	0.027 (2)	0.033 (3)	0.0026 (18)	−0.007 (2)	−0.0057 (19)
C5	0.042 (3)	0.037 (3)	0.042 (3)	0.010 (2)	−0.008 (2)	−0.014 (2)
C6	0.042 (3)	0.034 (3)	0.047 (3)	0.003 (2)	−0.012 (2)	−0.016 (2)
C7	0.025 (2)	0.028 (2)	0.026 (2)	−0.0016 (17)	−0.0043 (18)	−0.0055 (18)
C8	0.030 (2)	0.024 (2)	0.031 (2)	−0.0031 (18)	−0.004 (2)	−0.0072 (19)
C9	0.032 (2)	0.026 (2)	0.024 (2)	−0.0057 (18)	−0.0034 (19)	−0.0038 (18)
C10	0.033 (3)	0.027 (2)	0.035 (3)	−0.0016 (19)	−0.006 (2)	−0.005 (2)
C11	0.039 (3)	0.029 (2)	0.031 (3)	−0.006 (2)	−0.003 (2)	−0.002 (2)
C12	0.032 (3)	0.037 (3)	0.057 (4)	−0.005 (2)	−0.007 (3)	0.002 (3)
C13	0.034 (3)	0.033 (3)	0.051 (3)	−0.010 (2)	−0.013 (2)	0.007 (2)
C14	0.024 (2)	0.035 (3)	0.036 (3)	−0.0007 (19)	0.001 (2)	−0.013 (2)
C15	0.032 (3)	0.026 (2)	0.031 (3)	0.0012 (18)	−0.004 (2)	−0.0072 (19)
C16	0.027 (2)	0.023 (2)	0.026 (2)	−0.0028 (17)	−0.0045 (18)	−0.0044 (17)
C17	0.036 (3)	0.021 (2)	0.023 (2)	−0.0039 (18)	−0.0069 (19)	−0.0032 (17)
C18	0.051 (4)	0.046 (3)	0.050 (4)	−0.009 (3)	−0.006 (3)	−0.009 (3)
C19	0.040 (3)	0.069 (4)	0.044 (3)	−0.003 (3)	−0.001 (3)	−0.021 (3)
C20	0.045 (3)	0.060 (4)	0.045 (3)	0.003 (3)	0.000 (3)	−0.021 (3)
C21	0.049 (3)	0.044 (3)	0.043 (3)	0.003 (2)	−0.009 (3)	−0.017 (3)
C22	0.036 (3)	0.042 (3)	0.028 (3)	−0.004 (2)	−0.008 (2)	−0.013 (2)

Mn1—O2i	2.122 (4)	C5—C6	1.495 (8)
Mn1—O2	2.122 (4)	C5—H5A	0.9700
Mn1—O1i	2.153 (3)	C5—H5B	0.9700
Mn1—O1	2.153 (3)	C6—H6A	0.9700
Mn1—O1Wi	2.229 (4)	C6—H6B	0.9700
Mn1—O1W	2.229 (4)	C7—C8	1.403 (6)
F1—C14	1.363 (5)	C7—C16	1.410 (6)
N1—C3	1.342 (6)	C8—C9	1.386 (6)
N1—C7	1.386 (6)	C8—H8A	0.9300
N1—C4	1.458 (6)	C9—C14	1.408 (7)
N2—C9	1.413 (5)	C10—C11	1.526 (6)
N2—C10	1.456 (6)	C10—H10A	0.9700
N2—C13	1.476 (7)	C10—H10B	0.9700
N3—C11	1.463 (7)	C11—H11A	0.9700
N3—C12	1.487 (7)	C11—H11B	0.9700
N3—H3B	0.8600	C12—C13	1.516 (7)
N4—C18	1.343 (7)	C12—H12A	0.9700
N4—C22	1.356 (7)	C12—H12B	0.9700
O1—C17	1.273 (5)	C13—H13A	0.9700
O1W—H1WA	0.86 (2)	C13—H13B	0.9700
O1W—H1WB	0.86 (2)	C14—C15	1.356 (6)
O2—C1	1.255 (6)	C15—C16	1.409 (6)
O2W—H2WB	0.8500	C15—H15A	0.9300
O2W—H2WA	0.765 (18)	C16—C17	1.456 (6)
O3—C1	1.246 (6)	C18—C19	1.381 (9)
O3W—H3WA	0.8501	C18—H18A	0.9300
O3W—H3WB	0.8501	C19—C20	1.379 (9)
C1—C2	1.501 (6)	C19—H19A	0.9300
C2—C3	1.377 (6)	C20—C21	1.372 (8)
C2—C17	1.420 (7)	C20—H20A	0.9300
C3—H3A	0.9300	C21—C22	1.388 (7)
C4—C6	1.481 (7)	C21—H21A	0.9300
C4—C5	1.497 (7)	C22—C22ii	1.483 (10)
C4—H4A	0.9800
O2i—Mn1—O2	180.00 (9)	N1—C7—C16	117.9 (4)
O2i—Mn1—O1i	83.55 (13)	C8—C7—C16	120.3 (4)
O2—Mn1—O1i	96.45 (13)	C9—C8—C7	121.2 (4)
O2i—Mn1—O1	96.45 (13)	C9—C8—H8A	119.4
O2—Mn1—O1	83.55 (13)	C7—C8—H8A	119.4
O1i—Mn1—O1	180.00 (19)	C8—C9—C14	116.5 (4)
O2i—Mn1—O1Wi	90.83 (16)	C8—C9—N2	124.3 (4)
O2—Mn1—O1Wi	89.17 (16)	C14—C9—N2	119.2 (4)
O1i—Mn1—O1Wi	89.33 (14)	N2—C10—C11	109.3 (4)
O1—Mn1—O1Wi	90.67 (14)	N2—C10—H10A	109.8
O2i—Mn1—O1W	89.17 (16)	C11—C10—H10A	109.8
O2—Mn1—O1W	90.83 (16)	N2—C10—H10B	109.8
O1i—Mn1—O1W	90.67 (14)	C11—C10—H10B	109.8
O1—Mn1—O1W	89.33 (14)	H10A—C10—H10B	108.3
O1Wi—Mn1—O1W	180.0	N3—C11—C10	110.1 (4)
C3—N1—C7	119.8 (4)	N3—C11—H11A	109.6
C3—N1—C4	119.7 (4)	C10—C11—H11A	109.6
C7—N1—C4	120.4 (4)	N3—C11—H11B	109.6
C9—N2—C10	115.5 (4)	C10—C11—H11B	109.6
C9—N2—C13	113.4 (4)	H11A—C11—H11B	108.2
C10—N2—C13	110.5 (4)	N3—C12—C13	109.0 (4)
C11—N3—C12	109.6 (4)	N3—C12—H12A	109.9
C11—N3—H3B	125.2	C13—C12—H12A	109.9
C12—N3—H3B	125.2	N3—C12—H12B	109.9
C18—N4—C22	117.1 (5)	C13—C12—H12B	109.9
C17—O1—Mn1	128.5 (3)	H12A—C12—H12B	108.3
Mn1—O1W—H1WA	125 (4)	N2—C13—C12	110.3 (5)
Mn1—O1W—H1WB	121 (4)	N2—C13—H13A	109.6
H1WA—O1W—H1WB	98 (3)	C12—C13—H13A	109.6
C1—O2—Mn1	134.5 (3)	N2—C13—H13B	109.6
H2WB—O2W—H2WA	105.2	C12—C13—H13B	109.6
H3WA—O3W—H3WB	117.2	H13A—C13—H13B	108.1
O3—C1—O2	123.2 (4)	C15—C14—F1	117.9 (4)
O3—C1—C2	117.1 (4)	C15—C14—C9	124.0 (4)
O2—C1—C2	119.6 (4)	F1—C14—C9	118.1 (4)
C3—C2—C17	118.2 (4)	C14—C15—C16	119.3 (4)
C3—C2—C1	116.2 (4)	C14—C15—H15A	120.3
C17—C2—C1	125.5 (4)	C16—C15—H15A	120.3
N1—C3—C2	125.4 (4)	C15—C16—C7	118.3 (4)
N1—C3—H3A	117.3	C15—C16—C17	119.8 (4)
C2—C3—H3A	117.3	C7—C16—C17	121.9 (4)
N1—C4—C6	118.5 (4)	O1—C17—C2	125.9 (4)
N1—C4—C5	119.1 (4)	O1—C17—C16	117.9 (4)
C6—C4—C5	60.3 (4)	C2—C17—C16	116.1 (4)
N1—C4—H4A	115.9	N4—C18—C19	124.5 (6)
C6—C4—H4A	115.9	N4—C18—H18A	117.7
C5—C4—H4A	115.9	C19—C18—H18A	117.7
C6—C5—C4	59.3 (3)	C20—C19—C18	117.3 (6)
C6—C5—H5A	117.8	C20—C19—H19A	121.4
C4—C5—H5A	117.8	C18—C19—H19A	121.4
C6—C5—H5B	117.8	C21—C20—C19	119.9 (6)
C4—C5—H5B	117.8	C21—C20—H20A	120.1
H5A—C5—H5B	115.0	C19—C20—H20A	120.1
C4—C6—C5	60.4 (3)	C20—C21—C22	119.6 (5)
C4—C6—H6A	117.7	C20—C21—H21A	120.2
C5—C6—H6A	117.7	C22—C21—H21A	120.2
C4—C6—H6B	117.7	N4—C22—C21	121.6 (5)
C5—C6—H6B	117.7	N4—C22—C22ii	116.2 (6)
H6A—C6—H6B	114.9	C21—C22—C22ii	122.2 (6)
N1—C7—C8	121.7 (4)
O2—Mn1—O1—C17	14.4 (4)	C13—N2—C10—C11	58.6 (6)
O1i—Mn1—O1—C17	−42 (43)	C12—N3—C11—C10	60.2 (5)
O1Wi—Mn1—O1—C17	−74.7 (4)	N2—C10—C11—N3	−59.6 (5)
O1W—Mn1—O1—C17	105.3 (4)	C11—N3—C12—C13	−59.4 (6)
O1i—Mn1—O2—C1	165.3 (5)	C9—N2—C13—C12	169.4 (4)
O1—Mn1—O2—C1	−14.7 (5)	C10—N2—C13—C12	−59.1 (6)
O1Wi—Mn1—O2—C1	76.1 (5)	N3—C12—C13—N2	58.6 (7)
O1W—Mn1—O2—C1	−103.9 (5)	C8—C9—C14—C15	−5.4 (8)
Mn1—O2—C1—O3	−173.9 (4)	N2—C9—C14—C15	176.6 (5)
Mn1—O2—C1—C2	7.6 (8)	C8—C9—C14—F1	173.1 (4)
O3—C1—C2—C3	8.7 (7)	N2—C9—C14—F1	−4.8 (7)
O2—C1—C2—C3	−172.7 (5)	F1—C14—C15—C16	−177.0 (4)
O3—C1—C2—C17	−171.9 (5)	C9—C14—C15—C16	1.6 (8)
O2—C1—C2—C17	6.6 (8)	C14—C15—C16—C7	3.9 (7)
C7—N1—C3—C2	6.1 (8)	C14—C15—C16—C17	−176.7 (5)
C4—N1—C3—C2	−176.1 (5)	N1—C7—C16—C15	175.4 (4)
C17—C2—C3—N1	−2.1 (8)	C8—C7—C16—C15	−5.5 (7)
C1—C2—C3—N1	177.3 (5)	N1—C7—C16—C17	−4.0 (7)
C3—N1—C4—C6	108.4 (5)	C8—C7—C16—C17	175.1 (4)
C7—N1—C4—C6	−73.9 (6)	Mn1—O1—C17—C2	−8.3 (7)
C3—N1—C4—C5	38.5 (7)	Mn1—O1—C17—C16	169.7 (3)
C7—N1—C4—C5	−143.8 (5)	C3—C2—C17—O1	173.5 (5)
N1—C4—C5—C6	108.1 (5)	C1—C2—C17—O1	−5.9 (8)
N1—C4—C6—C5	−109.1 (5)	C3—C2—C17—C16	−4.6 (6)
C3—N1—C7—C8	178.1 (5)	C1—C2—C17—C16	176.0 (4)
C4—N1—C7—C8	0.4 (7)	C15—C16—C17—O1	10.1 (7)
C3—N1—C7—C16	−2.8 (7)	C7—C16—C17—O1	−170.6 (4)
C4—N1—C7—C16	179.4 (4)	C15—C16—C17—C2	−171.7 (4)
N1—C7—C8—C9	−179.3 (4)	C7—C16—C17—C2	7.7 (7)
C16—C7—C8—C9	1.7 (7)	C22—N4—C18—C19	1.2 (9)
C7—C8—C9—C14	3.7 (7)	N4—C18—C19—C20	−0.7 (10)
C7—C8—C9—N2	−178.5 (4)	C18—C19—C20—C21	0.9 (10)
C10—N2—C9—C8	−8.4 (7)	C19—C20—C21—C22	−1.6 (10)
C13—N2—C9—C8	120.5 (5)	C18—N4—C22—C21	−1.8 (8)
C10—N2—C9—C14	169.4 (5)	C18—N4—C22—C22ii	179.4 (6)
C13—N2—C9—C14	−61.7 (6)	C20—C21—C22—N4	2.1 (9)
C9—N2—C10—C11	−171.1 (4)	C20—C21—C22—C22ii	−179.3 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O3iii	0.86	2.22	2.661 (5)	112
O1W—H1WA···N4iv	0.86 (2)	2.03 (2)	2.880 (6)	171 (7)
O3W—H3WB···O2Wiv	0.85	2.13	2.910 (4)	153
O1W—H1WB···O3W	0.86 (2)	2.15 (2)	3.009 (5)	170 (6)
O2W—H2WA···N3	0.77 (2)	2.53 (3)	3.125 (5)	136 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯O3i	0.86	2.22	2.661 (5)	112
O1W—H1WA⋯N4ii	0.86 (2)	2.03 (2)	2.880 (6)	171 (7)
O3W—H3WB⋯O2Wii	0.85	2.13	2.910 (4)	153
O1W—H1WB⋯O3W	0.86 (2)	2.15 (2)	3.009 (5)	170 (6)
O2W—H2WA⋯N3	0.765 (18)	2.53 (3)	3.125 (5)	136 (4)

Symmetry codes: (i) ; (ii) .