4-(3-Carb-oxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 4-carb-oxy-benzoate-benzene-1,4-dicarb-oxy-lic acid (2/1).

In the title compound, C(16)H(19)FN(3)O(3) (+)·C(8)H(5)O(4) (-)·0.5C(8)H(6)O(4), the benzene-1,4-dicarb-oxy-lic acid mol-ecule is located on a centre of symmetry. In the crystal, the mol-ecules and ions are connected by inter-molecular C-H⋯O and O-H⋯O hydrogen bonds and π-π stacking inter-actions [with a centroid-centroid distance of 3.402 (2) Å], generating a three-dimensional supra-molecular structure.

Related literature

For general background to the use of quinolones in the treatment of infections, see: Barbas et al. (2006 ▶); Basavoju et al.(2006 ▶); Xiao et al. (2005 ▶).

Experimental

Crystal data

C16H19FN3O3 +·C8H5O4 −·0.5C8H6O4

M = 568.53

Triclinic,

a = 9.8901 (15) Å

b = 10.2420 (16) Å

c = 13.665 (2) Å

α = 89.304 (2)°

β = 74.672 (2)°

γ = 71.677 (2)°

V = 1263.5 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 296 K

0.46 × 0.45 × 0.36 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.948, T max = 0.959

10704 measured reflections

5143 independent reflections

4031 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.137

S = 1.00

5143 reflections

394 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811009524/ff2003sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811009524/ff2003Isup2.hkl

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

C16H19FN3O3+·C8H5O4−·0.5C8H6O4	Z = 2
Mr = 568.53	F(000) = 594
Triclinic, P1	Dx = 1.494 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8901 (15) Å	Cell parameters from 10704 reflections
b = 10.2420 (16) Å	θ = 2.5–26.4°
c = 13.665 (2) Å	µ = 0.12 mm−1
α = 89.304 (2)°	T = 296 K
β = 74.672 (2)°	Block, yellow
γ = 71.677 (2)°	0.46 × 0.45 × 0.36 mm
V = 1263.5 (3) Å3

Bruker APEX CCD area-detector diffractometer	5143 independent reflections
Radiation source: fine-focus sealed tube	4031 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.948, Tmax = 0.959	k = −12→12
10704 measured reflections	l = −17→17

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.095P)2] where P = (Fo2 + 2Fc2)/3
5143 reflections	(Δ/σ)max < 0.001
394 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.28 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
F1	0.63577 (11)	0.18180 (9)	0.27698 (7)	0.0431 (3)
C1	0.63370 (16)	−0.02848 (19)	0.79008 (11)	0.0389 (4)
C2	0.65495 (15)	−0.05532 (16)	0.68003 (10)	0.0307 (3)
C3	0.63043 (15)	0.05539 (15)	0.61573 (11)	0.0290 (3)
C4	0.66237 (14)	0.01485 (14)	0.50870 (10)	0.0258 (3)
C5	0.64110 (15)	0.11621 (15)	0.43912 (10)	0.0275 (3)
H5A	0.6076	0.2090	0.4619	0.033*
C6	0.66906 (15)	0.07966 (14)	0.33949 (10)	0.0276 (3)
C7	0.72669 (15)	−0.05884 (15)	0.29813 (10)	0.0264 (3)
C8	0.75114 (15)	−0.15922 (15)	0.36672 (10)	0.0277 (3)
H8A	0.7915	−0.2517	0.3427	0.033*
C9	0.71625 (14)	−0.12410 (14)	0.47136 (10)	0.0258 (3)
C10	0.70628 (16)	−0.18915 (16)	0.63933 (11)	0.0320 (3)
H10A	0.7198	−0.2588	0.6836	0.038*
C11	0.79437 (18)	−0.37552 (16)	0.50584 (12)	0.0397 (4)
H11A	0.8377	−0.4277	0.5560	0.048*
H11B	0.8717	−0.3910	0.4423	0.048*
C12	0.6737 (2)	−0.42777 (18)	0.49078 (15)	0.0524 (5)
H12A	0.7149	−0.5242	0.4686	0.079*
H12B	0.6316	−0.3776	0.4403	0.079*
H12C	0.5979	−0.4147	0.5539	0.079*
C13	0.82815 (18)	−0.02111 (17)	0.11838 (11)	0.0367 (4)
H13A	0.9339	−0.0663	0.1060	0.044*
H13B	0.8050	0.0741	0.1427	0.044*
C14	0.78474 (18)	−0.02599 (16)	0.02080 (11)	0.0377 (4)
H14A	0.6795	0.0219	0.0328	0.045*
H14B	0.8381	0.0201	−0.0302	0.045*
C15	0.74848 (17)	−0.24840 (16)	0.06232 (11)	0.0353 (4)
H15A	0.7813	−0.3450	0.0383	0.042*
H15B	0.6419	−0.2125	0.0739	0.042*
C16	0.78617 (19)	−0.23578 (15)	0.16120 (11)	0.0363 (4)
H16A	0.7325	−0.2810	0.2127	0.044*
H16B	0.8913	−0.2813	0.1517	0.044*
C17	0.17400 (16)	0.50636 (16)	0.20944 (11)	0.0330 (3)
C18	0.33786 (15)	0.48186 (14)	0.18335 (11)	0.0290 (3)
C19	0.43591 (16)	0.39424 (16)	0.10056 (12)	0.0350 (3)
H19A	0.4000	0.3534	0.0571	0.042*
C20	0.58733 (16)	0.36724 (16)	0.08232 (11)	0.0344 (3)
H20A	0.6523	0.3088	0.0264	0.041*
C21	0.64275 (15)	0.42664 (14)	0.14690 (11)	0.0281 (3)
C22	0.54455 (16)	0.51661 (16)	0.22799 (12)	0.0348 (3)
H22A	0.5804	0.5588	0.2707	0.042*
C23	0.39284 (16)	0.54453 (16)	0.24616 (12)	0.0356 (4)
H23A	0.3278	0.6056	0.3007	0.043*
C24	0.80895 (16)	0.38823 (15)	0.12883 (12)	0.0321 (3)
C25	0.97781 (16)	0.15488 (18)	0.32394 (12)	0.0371 (4)
C26	0.98985 (15)	0.07643 (17)	0.41574 (11)	0.0330 (3)
C27	1.04199 (16)	−0.06690 (17)	0.40371 (12)	0.0354 (4)
H27A	1.0697	−0.1117	0.3392	0.042*
C28	1.05276 (16)	−0.14308 (18)	0.48721 (12)	0.0356 (4)
H28	1.087 (2)	−0.246 (2)	0.4790 (14)	0.054 (5)*
N1	0.74725 (14)	−0.09079 (12)	0.19528 (9)	0.0306 (3)
N2	0.81977 (15)	−0.17166 (14)	−0.01670 (9)	0.0327 (3)
H2A	0.923 (2)	−0.2219 (19)	−0.0393 (13)	0.049 (5)*
H2B	0.785 (2)	−0.169 (2)	−0.0715 (15)	0.055 (5)*
N3	0.73831 (13)	−0.22629 (12)	0.54007 (9)	0.0305 (3)
O1	0.60295 (14)	0.10171 (15)	0.82150 (9)	0.0489 (3)
H1A	0.595 (3)	0.154 (3)	0.760 (2)	0.104 (9)*
O2	0.64619 (14)	−0.11994 (15)	0.84810 (9)	0.0522 (3)
O3	0.58611 (12)	0.18033 (11)	0.64870 (8)	0.0391 (3)
O4	0.08777 (13)	0.57308 (16)	0.28487 (10)	0.0622 (4)
O5	0.13363 (12)	0.44329 (13)	0.14372 (9)	0.0466 (3)
H5B	0.030 (3)	0.448 (2)	0.1690 (17)	0.087 (7)*
O6	0.88873 (12)	0.30848 (14)	0.05353 (9)	0.0533 (3)
O7	0.85565 (11)	0.43952 (11)	0.19277 (9)	0.0379 (3)
O8	1.01763 (14)	0.10184 (13)	0.23849 (9)	0.0520 (3)
O9	0.91792 (16)	0.28979 (13)	0.34610 (10)	0.0565 (4)
H9A	0.903 (3)	0.334 (2)	0.2932 (18)	0.080 (8)*

	U11	U22	U33	U12	U13	U23
F1	0.0595 (6)	0.0329 (5)	0.0350 (5)	−0.0096 (4)	−0.0165 (4)	0.0123 (4)
C1	0.0302 (8)	0.0629 (11)	0.0270 (8)	−0.0185 (8)	−0.0093 (6)	0.0033 (8)
C2	0.0241 (7)	0.0454 (9)	0.0242 (7)	−0.0122 (6)	−0.0079 (6)	0.0031 (6)
C3	0.0215 (6)	0.0374 (8)	0.0271 (7)	−0.0080 (6)	−0.0069 (5)	−0.0025 (6)
C4	0.0208 (6)	0.0323 (8)	0.0245 (7)	−0.0080 (6)	−0.0069 (5)	0.0007 (6)
C5	0.0259 (7)	0.0254 (7)	0.0295 (7)	−0.0062 (6)	−0.0071 (6)	−0.0001 (6)
C6	0.0281 (7)	0.0284 (7)	0.0284 (7)	−0.0092 (6)	−0.0113 (6)	0.0079 (6)
C7	0.0265 (7)	0.0333 (8)	0.0221 (7)	−0.0127 (6)	−0.0075 (5)	0.0013 (6)
C8	0.0280 (7)	0.0262 (7)	0.0266 (7)	−0.0058 (6)	−0.0072 (6)	−0.0001 (5)
C9	0.0218 (6)	0.0307 (7)	0.0246 (7)	−0.0077 (6)	−0.0073 (5)	0.0043 (6)
C10	0.0291 (7)	0.0420 (9)	0.0265 (7)	−0.0106 (6)	−0.0114 (6)	0.0087 (6)
C11	0.0431 (9)	0.0297 (8)	0.0338 (8)	0.0027 (7)	−0.0076 (7)	0.0049 (6)
C12	0.0648 (12)	0.0311 (9)	0.0544 (11)	−0.0102 (8)	−0.0109 (9)	−0.0027 (8)
C13	0.0433 (9)	0.0441 (9)	0.0285 (8)	−0.0239 (7)	−0.0079 (6)	0.0049 (6)
C14	0.0460 (9)	0.0390 (9)	0.0270 (8)	−0.0145 (7)	−0.0073 (7)	0.0066 (6)
C15	0.0378 (8)	0.0392 (9)	0.0290 (8)	−0.0145 (7)	−0.0066 (6)	−0.0042 (6)
C16	0.0504 (9)	0.0330 (8)	0.0267 (8)	−0.0152 (7)	−0.0103 (7)	0.0006 (6)
C17	0.0268 (7)	0.0366 (8)	0.0350 (8)	−0.0092 (6)	−0.0087 (6)	0.0019 (6)
C18	0.0255 (7)	0.0310 (7)	0.0320 (8)	−0.0101 (6)	−0.0090 (6)	0.0048 (6)
C19	0.0310 (8)	0.0404 (9)	0.0365 (8)	−0.0125 (7)	−0.0126 (6)	−0.0041 (7)
C20	0.0291 (8)	0.0369 (8)	0.0339 (8)	−0.0078 (6)	−0.0066 (6)	−0.0035 (6)
C21	0.0251 (7)	0.0276 (7)	0.0341 (8)	−0.0099 (6)	−0.0106 (6)	0.0080 (6)
C22	0.0305 (8)	0.0378 (8)	0.0388 (8)	−0.0130 (6)	−0.0116 (6)	−0.0044 (7)
C23	0.0295 (8)	0.0366 (8)	0.0371 (8)	−0.0086 (6)	−0.0053 (6)	−0.0072 (6)
C24	0.0253 (7)	0.0329 (8)	0.0392 (8)	−0.0097 (6)	−0.0108 (6)	0.0093 (6)
C25	0.0283 (7)	0.0475 (10)	0.0373 (9)	−0.0137 (7)	−0.0104 (6)	0.0057 (7)
C26	0.0224 (7)	0.0436 (9)	0.0349 (8)	−0.0123 (6)	−0.0091 (6)	0.0047 (6)
C27	0.0264 (7)	0.0459 (9)	0.0331 (8)	−0.0107 (7)	−0.0079 (6)	−0.0004 (7)
C28	0.0272 (7)	0.0412 (9)	0.0389 (9)	−0.0113 (7)	−0.0093 (6)	0.0020 (7)
N1	0.0415 (7)	0.0314 (7)	0.0225 (6)	−0.0164 (5)	−0.0090 (5)	0.0023 (5)
N2	0.0295 (7)	0.0435 (8)	0.0228 (6)	−0.0085 (6)	−0.0070 (5)	−0.0016 (5)
N3	0.0306 (6)	0.0311 (7)	0.0263 (6)	−0.0045 (5)	−0.0089 (5)	0.0046 (5)
O1	0.0497 (7)	0.0647 (8)	0.0289 (6)	−0.0152 (6)	−0.0086 (5)	−0.0086 (6)
O2	0.0622 (8)	0.0773 (9)	0.0300 (6)	−0.0324 (7)	−0.0226 (6)	0.0168 (6)
O3	0.0424 (6)	0.0386 (6)	0.0321 (6)	−0.0085 (5)	−0.0082 (5)	−0.0078 (5)
O4	0.0288 (6)	0.0954 (11)	0.0531 (8)	−0.0150 (6)	−0.0005 (6)	−0.0288 (7)
O5	0.0263 (6)	0.0604 (8)	0.0531 (7)	−0.0146 (5)	−0.0095 (5)	−0.0155 (6)
O6	0.0265 (6)	0.0708 (9)	0.0519 (8)	−0.0039 (6)	−0.0068 (5)	−0.0122 (6)
O7	0.0282 (5)	0.0403 (6)	0.0514 (7)	−0.0136 (5)	−0.0183 (5)	0.0077 (5)
O8	0.0606 (8)	0.0560 (8)	0.0367 (7)	−0.0143 (6)	−0.0146 (6)	0.0056 (6)
O9	0.0783 (10)	0.0429 (8)	0.0424 (8)	−0.0081 (7)	−0.0208 (7)	0.0090 (6)

F1—C6	1.3576 (16)	C15—H15A	0.9700
C1—O2	1.217 (2)	C15—H15B	0.9700
C1—O1	1.321 (2)	C16—N1	1.4604 (18)
C1—C2	1.479 (2)	C16—H16A	0.9700
C2—C10	1.370 (2)	C16—H16B	0.9700
C2—C3	1.426 (2)	C17—O4	1.2012 (18)
C3—O3	1.2607 (18)	C17—O5	1.3225 (18)
C3—C4	1.4490 (19)	C17—C18	1.5025 (19)
C4—C9	1.402 (2)	C18—C19	1.387 (2)
C4—C5	1.404 (2)	C18—C23	1.387 (2)
C5—C6	1.349 (2)	C19—C20	1.388 (2)
C5—H5A	0.9300	C19—H19A	0.9300
C6—C7	1.413 (2)	C20—C21	1.389 (2)
C7—C8	1.391 (2)	C20—H20A	0.9300
C7—N1	1.3936 (17)	C21—C22	1.383 (2)
C8—C9	1.4023 (19)	C21—C24	1.5162 (19)
C8—H8A	0.9300	C22—C23	1.389 (2)
C9—N3	1.4020 (18)	C22—H22A	0.9300
C10—N3	1.3397 (18)	C23—H23A	0.9300
C10—H10A	0.9300	C24—O6	1.2388 (18)
C11—N3	1.4865 (19)	C24—O7	1.2766 (18)
C11—C12	1.513 (3)	C25—O8	1.2048 (19)
C11—H11A	0.9700	C25—O9	1.324 (2)
C11—H11B	0.9700	C25—C26	1.493 (2)
C12—H12A	0.9600	C26—C27	1.390 (2)
C12—H12B	0.9600	C26—C28i	1.396 (2)
C12—H12C	0.9600	C27—C28	1.383 (2)
C13—N1	1.4663 (18)	C27—H27A	0.9300
C13—C14	1.511 (2)	C28—C26i	1.396 (2)
C13—H13A	0.9700	C28—H28	1.00 (2)
C13—H13B	0.9700	N2—H2A	0.95 (2)
C14—N2	1.486 (2)	N2—H2B	0.90 (2)
C14—H14A	0.9700	O1—H1A	1.01 (3)
C14—H14B	0.9700	O5—H5B	0.97 (3)
C15—N2	1.4854 (19)	O9—H9A	0.87 (2)
C15—C16	1.511 (2)
O2—C1—O1	121.77 (15)	H15A—C15—H15B	108.0
O2—C1—C2	122.66 (16)	N1—C16—C15	110.42 (12)
O1—C1—C2	115.55 (15)	N1—C16—H16A	109.6
C10—C2—C3	120.06 (13)	C15—C16—H16A	109.6
C10—C2—C1	118.91 (14)	N1—C16—H16B	109.6
C3—C2—C1	120.95 (14)	C15—C16—H16B	109.6
O3—C3—C2	122.78 (13)	H16A—C16—H16B	108.1
O3—C3—C4	121.79 (13)	O4—C17—O5	122.82 (14)
C2—C3—C4	115.42 (13)	O4—C17—C18	123.26 (14)
C9—C4—C5	118.25 (12)	O5—C17—C18	113.87 (13)
C9—C4—C3	121.91 (13)	C19—C18—C23	119.20 (13)
C5—C4—C3	119.84 (13)	C19—C18—C17	121.79 (13)
C6—C5—C4	120.33 (13)	C23—C18—C17	118.96 (13)
C6—C5—H5A	119.8	C18—C19—C20	120.29 (13)
C4—C5—H5A	119.8	C18—C19—H19A	119.9
C5—C6—F1	117.76 (12)	C20—C19—H19A	119.9
C5—C6—C7	123.34 (13)	C19—C20—C21	120.57 (14)
F1—C6—C7	118.88 (12)	C19—C20—H20A	119.7
C8—C7—N1	122.74 (13)	C21—C20—H20A	119.7
C8—C7—C6	116.28 (12)	C22—C21—C20	119.00 (12)
N1—C7—C6	120.84 (12)	C22—C21—C24	121.62 (13)
C7—C8—C9	121.46 (13)	C20—C21—C24	119.35 (13)
C7—C8—H8A	119.3	C21—C22—C23	120.57 (13)
C9—C8—H8A	119.3	C21—C22—H22A	119.7
N3—C9—C4	118.79 (12)	C23—C22—H22A	119.7
N3—C9—C8	120.97 (12)	C18—C23—C22	120.33 (14)
C4—C9—C8	120.22 (13)	C18—C23—H23A	119.8
N3—C10—C2	124.37 (14)	C22—C23—H23A	119.8
N3—C10—H10A	117.8	O6—C24—O7	125.16 (13)
C2—C10—H10A	117.8	O6—C24—C21	117.30 (13)
N3—C11—C12	112.40 (13)	O7—C24—C21	117.54 (13)
N3—C11—H11A	109.1	O8—C25—O9	123.17 (15)
C12—C11—H11A	109.1	O8—C25—C26	123.95 (15)
N3—C11—H11B	109.1	O9—C25—C26	112.88 (14)
C12—C11—H11B	109.1	C27—C26—C28i	119.59 (15)
H11A—C11—H11B	107.9	C27—C26—C25	118.64 (14)
C11—C12—H12A	109.5	C28i—C26—C25	121.76 (15)
C11—C12—H12B	109.5	C28—C27—C26	120.27 (15)
H12A—C12—H12B	109.5	C28—C27—H27A	119.9
C11—C12—H12C	109.5	C26—C27—H27A	119.9
H12A—C12—H12C	109.5	C27—C28—C26i	120.14 (15)
H12B—C12—H12C	109.5	C27—C28—H28	120.3 (11)
N1—C13—C14	109.50 (12)	C26i—C28—H28	119.5 (11)
N1—C13—H13A	109.8	C7—N1—C16	117.61 (12)
C14—C13—H13A	109.8	C7—N1—C13	119.55 (11)
N1—C13—H13B	109.8	C16—N1—C13	110.22 (11)
C14—C13—H13B	109.8	C15—N2—C14	111.24 (11)
H13A—C13—H13B	108.2	C15—N2—H2A	108.2 (11)
N2—C14—C13	109.94 (13)	C14—N2—H2A	114.5 (11)
N2—C14—H14A	109.7	C15—N2—H2B	109.8 (13)
C13—C14—H14A	109.7	C14—N2—H2B	106.8 (12)
N2—C14—H14B	109.7	H2A—N2—H2B	106.1 (15)
C13—C14—H14B	109.7	C10—N3—C9	119.45 (12)
H14A—C14—H14B	108.2	C10—N3—C11	118.90 (12)
N2—C15—C16	111.36 (12)	C9—N3—C11	121.65 (11)
N2—C15—H15A	109.4	C1—O1—H1A	105.0 (15)
C16—C15—H15A	109.4	C17—O5—H5B	111.4 (13)
N2—C15—H15B	109.4	C25—O9—H9A	112.3 (15)
C16—C15—H15B	109.4
O2—C1—C2—C10	−7.3 (2)	C18—C19—C20—C21	0.4 (2)
O1—C1—C2—C10	171.42 (13)	C19—C20—C21—C22	−2.0 (2)
O2—C1—C2—C3	176.10 (13)	C19—C20—C21—C24	176.19 (13)
O1—C1—C2—C3	−5.2 (2)	C20—C21—C22—C23	1.6 (2)
C10—C2—C3—O3	−178.58 (13)	C24—C21—C22—C23	−176.53 (14)
C1—C2—C3—O3	−2.0 (2)	C19—C18—C23—C22	−1.9 (2)
C10—C2—C3—C4	0.41 (19)	C17—C18—C23—C22	175.66 (14)
C1—C2—C3—C4	176.99 (12)	C21—C22—C23—C18	0.3 (2)
O3—C3—C4—C9	177.89 (12)	C22—C21—C24—O6	−178.99 (14)
C2—C3—C4—C9	−1.10 (19)	C20—C21—C24—O6	2.9 (2)
O3—C3—C4—C5	−1.3 (2)	C22—C21—C24—O7	1.6 (2)
C2—C3—C4—C5	179.68 (12)	C20—C21—C24—O7	−176.52 (13)
C9—C4—C5—C6	1.4 (2)	O8—C25—C26—C27	−3.9 (2)
C3—C4—C5—C6	−179.33 (12)	O9—C25—C26—C27	175.87 (13)
C4—C5—C6—F1	175.05 (11)	O8—C25—C26—C28i	177.53 (15)
C4—C5—C6—C7	−3.0 (2)	O9—C25—C26—C28i	−2.7 (2)
C5—C6—C7—C8	1.4 (2)	C28i—C26—C27—C28	−0.5 (2)
F1—C6—C7—C8	−176.64 (12)	C25—C26—C27—C28	−179.12 (13)
C5—C6—C7—N1	177.13 (13)	C26—C27—C28—C26i	0.5 (2)
F1—C6—C7—N1	−0.92 (19)	C8—C7—N1—C16	4.3 (2)
N1—C7—C8—C9	−173.88 (12)	C6—C7—N1—C16	−171.11 (13)
C6—C7—C8—C9	1.8 (2)	C8—C7—N1—C13	−133.83 (14)
C5—C4—C9—N3	179.84 (12)	C6—C7—N1—C13	50.73 (19)
C3—C4—C9—N3	0.61 (19)	C15—C16—N1—C7	158.69 (12)
C5—C4—C9—C8	1.64 (19)	C15—C16—N1—C13	−59.52 (16)
C3—C4—C9—C8	−177.59 (12)	C14—C13—N1—C7	−157.19 (13)
C7—C8—C9—N3	178.57 (12)	C14—C13—N1—C16	61.86 (16)
C7—C8—C9—C4	−3.3 (2)	C16—C15—N2—C14	−53.27 (17)
C3—C2—C10—N3	0.8 (2)	C13—C14—N2—C15	55.27 (16)
C1—C2—C10—N3	−175.81 (13)	C2—C10—N3—C9	−1.4 (2)
N1—C13—C14—N2	−59.34 (17)	C2—C10—N3—C11	179.53 (13)
N2—C15—C16—N1	55.06 (16)	C4—C9—N3—C10	0.64 (19)
O4—C17—C18—C19	174.08 (16)	C8—C9—N3—C10	178.82 (12)
O5—C17—C18—C19	−3.4 (2)	C4—C9—N3—C11	179.68 (12)
O4—C17—C18—C23	−3.4 (2)	C8—C9—N3—C11	−2.1 (2)
O5—C17—C18—C23	179.09 (14)	C12—C11—N3—C10	98.46 (16)
C23—C18—C19—C20	1.5 (2)	C12—C11—N3—C9	−80.58 (17)
C17—C18—C19—C20	−175.97 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15B···O1ii	0.97	2.38	3.274 (2)	153
O5—H5B···O7iii	0.97 (3)	1.70 (3)	2.6648 (15)	169 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15B⋯O1i	0.97	2.38	3.274 (2)	153
O5—H5B⋯O7ii	0.97 (3)	1.70 (3)	2.6648 (15)	169 (2)

Symmetry codes: (i) ; (ii) .