Lomefloxacinium picrate.

IN THE CATION OF THE TITLE COMPOUND [SYSTEMATIC NAME: (RS)-4-(3-carb-oxy-1-ethyl-6,8-difluoro-4-oxo-1,4-dihydro-quinolin-7-yl)-2-methyl-piperazin-1-ium 2,4,6-trinitro-phenolate], C(17)H(20)F(2)N(3)O(3) (+)·C(6)H(2)N(3)O(7) (-), the piper-azine ring adopts a slightly distorted chair conformation and contains a protonated N atom. An intra-molecular O-H⋯O hydrogen bond occurs in the cation. The dihedral angles between the mean planes of the six-atom piperazine ring and the 10-atom fused ring system is 43.3 (5)°. The picrate anion inter-acts with the protonated N atom of an adjacent cation through a bifurcated N-H⋯(O,O) three-center hydrogen bond. Strong N-H⋯O hydrogen bonds in concert with weak π-π stacking inter-actions [centroid-centroid distance = 3.6460 (14) Å] dominate the crystal packing, creating a two-dimensional network structure along [011].

Related literature

For background to lomefloxacin, see: Rubinstein et al. (2001 ▶). For related structures, see: Jasinski et al. (2009 ▶, 2010a ▶,b ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H20F2N3O3 +·C6H2N3O7 −

M = 580.47

Triclinic,

a = 10.9314 (4) Å

b = 11.6748 (4) Å

c = 12.0530 (4) Å

α = 92.969 (3)°

β = 115.555 (3)°

γ = 109.852 (3)°

V = 1269.14 (8) Å3

Z = 2

Cu Kα radiation

μ = 1.13 mm−1

T = 123 K

0.44 × 0.33 × 0.19 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.838, T max = 1.000

8890 measured reflections

5002 independent reflections

4423 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.198

S = 1.06

5002 reflections

373 parameters

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.59 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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 global, I. DOI: 10.1107/S1600536811002534/fl2332sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811002534/fl2332Isup2.hkl

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

C17H20F2N3O3+·C6H2N3O7−	Z = 2
Mr = 580.47	F(000) = 600
Triclinic, P1	Dx = 1.519 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 10.9314 (4) Å	Cell parameters from 6216 reflections
b = 11.6748 (4) Å	θ = 4.7–73.8°
c = 12.0530 (4) Å	µ = 1.13 mm−1
α = 92.969 (3)°	T = 123 K
β = 115.555 (3)°	Prism, pale yellow
γ = 109.852 (3)°	0.44 × 0.33 × 0.19 mm
V = 1269.14 (8) Å3

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	5002 independent reflections
Radiation source: Enhance (Cu) X-ray Source	4423 reflections with I > 2σ(I)
graphite	Rint = 0.018
Detector resolution: 10.5081 pixels mm-1	θmax = 74.0°, θmin = 4.7°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −14→14
Tmin = 0.838, Tmax = 1.000	l = −15→11
8890 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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.198	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0848P)2 + 0.7775P] where P = (Fo2 + 2Fc2)/3
5002 reflections	(Δ/σ)max = 0.011
373 parameters	Δρmax = 0.54 e Å−3
0 restraints	Δρmin = −0.59 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	Occ. (<1)
F1	0.6041 (2)	0.51552 (14)	0.14890 (17)	0.0702 (5)
F2	0.5633 (2)	0.21345 (13)	0.38653 (13)	0.0626 (5)
O1	0.1693 (3)	−0.2597 (2)	−0.1643 (2)	0.0873 (8)
O2	0.1665 (3)	−0.1195 (2)	−0.2795 (2)	0.0762 (7)
H2	0.1948	−0.0413	−0.2670	0.114*
O3	0.3100 (2)	0.1106 (2)	−0.17445 (17)	0.0677 (6)
N1	0.4330 (2)	0.01780 (17)	0.16877 (19)	0.0436 (5)
N2	0.6695 (3)	0.46292 (19)	0.3820 (2)	0.0533 (6)
N3	0.8631 (2)	0.67661 (19)	0.58301 (19)	0.0496 (5)
H3A	0.9470	0.7498	0.6208	0.060*
H3B	0.8207	0.6649	0.6352	0.060*
C1	0.3493 (3)	−0.0691 (2)	0.0590 (2)	0.0482 (6)
H1A	0.3202	−0.1545	0.0631	0.058*
C2	0.3035 (3)	−0.0441 (2)	−0.0569 (2)	0.0495 (6)
C3	0.3465 (3)	0.0821 (3)	−0.0690 (2)	0.0485 (6)
C4	0.4355 (2)	0.1778 (2)	0.0492 (2)	0.0418 (5)
C5	0.4789 (3)	0.3043 (2)	0.0451 (2)	0.0478 (6)
H5A	0.4542	0.3271	−0.0338	0.057*
C6	0.5558 (3)	0.3938 (2)	0.1536 (2)	0.0484 (6)
C7	0.5904 (3)	0.3680 (2)	0.2737 (2)	0.0435 (5)
C8	0.5437 (3)	0.2414 (2)	0.2746 (2)	0.0430 (5)
C9	0.4727 (2)	0.1443 (2)	0.1660 (2)	0.0391 (5)
C10	0.6250 (3)	0.5649 (3)	0.3947 (3)	0.0626 (8)
H10A	0.5717	0.5482	0.4448	0.075*
H10B	0.5562	0.5690	0.3098	0.075*
C11	0.7563 (3)	0.6884 (2)	0.4582 (3)	0.0592 (7)
H11A	0.8060	0.7051	0.4044	0.071*
C12	0.7179 (5)	0.7965 (3)	0.4768 (4)	0.0860 (12)
H12A	0.8083	0.8737	0.5171	0.129*
H12B	0.6708	0.7830	0.5309	0.129*
H12C	0.6495	0.8038	0.3946	0.129*
C13	0.9051 (3)	0.5702 (3)	0.5682 (3)	0.0572 (7)
H13A	0.9588	0.5861	0.5184	0.069*
H13B	0.9723	0.5637	0.6526	0.069*
C14	0.7718 (3)	0.4506 (2)	0.5035 (3)	0.0604 (8)
H14A	0.8010	0.3818	0.4899	0.072*
H14B	0.7229	0.4303	0.5567	0.072*
C15	0.4738 (3)	−0.0307 (2)	0.2860 (3)	0.0547 (6)
H15A	0.5682	0.0326	0.3549	0.066*
H15B	0.4897	−0.1073	0.2707	0.066*
C16	0.3574 (4)	−0.0604 (3)	0.3270 (3)	0.0721 (9)
H16A	0.3826	−0.1023	0.3970	0.108*
H16B	0.2612	−0.1157	0.2559	0.108*
H16C	0.3522	0.0173	0.3550	0.108*
C17	0.2083 (3)	−0.1516 (3)	−0.1695 (3)	0.0635 (8)
O1B	0.7431 (2)	0.60714 (18)	0.73716 (18)	0.0620 (5)
O2B	0.9064 (3)	0.8637 (2)	0.7905 (2)	0.0755 (7)
O3B	0.8490 (2)	0.94720 (17)	0.9138 (2)	0.0563 (5)
O4B	1.0085 (4)	0.8183 (3)	1.3141 (2)	0.0968 (9)
O5B	0.9630 (4)	0.6231 (3)	1.3095 (2)	0.0926 (8)
O6A	0.6327 (5)	0.3366 (3)	0.8566 (5)	0.1035 (10)	0.762 (4)
O7A	0.7909 (5)	0.3882 (3)	0.7890 (4)	0.1035 (10)	0.762 (4)
O6B	0.6273 (9)	0.3566 (9)	0.7639 (9)	0.1035 (10)	0.238 (4)
O7B	0.8257 (10)	0.3560 (9)	0.9080 (10)	0.1035 (10)	0.238 (4)
N1B	0.8724 (2)	0.86209 (18)	0.8747 (2)	0.0466 (5)
N2B	0.9639 (3)	0.7109 (3)	1.2577 (3)	0.0683 (7)
N3B	0.7447 (3)	0.4116 (2)	0.8604 (3)	0.0675 (7)
C1B	0.7998 (3)	0.6332 (2)	0.8548 (2)	0.0476 (6)
C2B	0.8633 (3)	0.7566 (2)	0.9345 (2)	0.0443 (5)
C3B	0.9121 (3)	0.7818 (2)	1.0621 (2)	0.0482 (6)
H3BA	0.9482	0.8649	1.1084	0.058*
C4B	0.9077 (3)	0.6843 (3)	1.1220 (3)	0.0544 (6)
C5B	0.8520 (3)	0.5620 (3)	1.0552 (3)	0.0593 (7)
H5BA	0.8492	0.4953	1.0972	0.071*
C6B	0.8019 (3)	0.5399 (2)	0.9289 (3)	0.0544 (6)

	U11	U22	U33	U12	U13	U23
F1	0.0779 (11)	0.0377 (8)	0.0661 (10)	0.0129 (8)	0.0173 (9)	0.0181 (7)
F2	0.0898 (12)	0.0390 (8)	0.0360 (7)	0.0139 (8)	0.0201 (7)	0.0050 (6)
O1	0.0778 (16)	0.0513 (13)	0.0785 (16)	0.0096 (11)	0.0083 (12)	−0.0238 (11)
O2	0.0637 (13)	0.0804 (15)	0.0460 (11)	0.0075 (12)	0.0134 (10)	−0.0153 (10)
O3	0.0677 (13)	0.0764 (14)	0.0347 (9)	0.0175 (11)	0.0137 (9)	0.0042 (9)
N1	0.0435 (10)	0.0321 (9)	0.0418 (10)	0.0140 (8)	0.0110 (8)	0.0012 (8)
N2	0.0547 (12)	0.0340 (10)	0.0436 (11)	0.0187 (9)	0.0010 (9)	−0.0036 (8)
N3	0.0522 (12)	0.0372 (10)	0.0396 (10)	0.0137 (9)	0.0098 (9)	−0.0036 (8)
C1	0.0421 (12)	0.0350 (11)	0.0525 (14)	0.0124 (10)	0.0141 (11)	−0.0045 (10)
C2	0.0391 (12)	0.0476 (14)	0.0442 (13)	0.0125 (10)	0.0111 (10)	−0.0091 (10)
C3	0.0392 (12)	0.0571 (15)	0.0373 (12)	0.0158 (11)	0.0123 (10)	−0.0010 (10)
C4	0.0376 (11)	0.0427 (12)	0.0350 (11)	0.0142 (9)	0.0111 (9)	0.0023 (9)
C5	0.0461 (13)	0.0479 (13)	0.0395 (12)	0.0169 (11)	0.0133 (10)	0.0124 (10)
C6	0.0460 (13)	0.0344 (11)	0.0507 (14)	0.0123 (10)	0.0139 (11)	0.0123 (10)
C7	0.0384 (11)	0.0345 (11)	0.0399 (12)	0.0117 (9)	0.0069 (9)	0.0007 (9)
C8	0.0448 (12)	0.0368 (11)	0.0331 (11)	0.0127 (9)	0.0098 (9)	0.0037 (9)
C9	0.0371 (11)	0.0337 (11)	0.0377 (11)	0.0129 (9)	0.0120 (9)	0.0033 (9)
C10	0.0559 (15)	0.0452 (14)	0.0604 (16)	0.0235 (12)	0.0049 (13)	−0.0038 (12)
C11	0.0684 (17)	0.0419 (13)	0.0485 (14)	0.0221 (13)	0.0131 (13)	0.0025 (11)
C12	0.109 (3)	0.0548 (18)	0.071 (2)	0.046 (2)	0.015 (2)	0.0017 (15)
C13	0.0565 (15)	0.0496 (14)	0.0442 (13)	0.0240 (12)	0.0056 (11)	−0.0034 (11)
C14	0.0648 (17)	0.0407 (13)	0.0462 (14)	0.0229 (12)	0.0017 (12)	−0.0015 (11)
C15	0.0656 (16)	0.0363 (12)	0.0500 (14)	0.0222 (12)	0.0160 (12)	0.0106 (10)
C16	0.082 (2)	0.0591 (17)	0.0626 (18)	0.0180 (16)	0.0319 (17)	0.0185 (14)
C17	0.0458 (14)	0.0654 (19)	0.0528 (16)	0.0132 (13)	0.0113 (12)	−0.0158 (13)
O1B	0.0670 (12)	0.0486 (10)	0.0480 (10)	0.0090 (9)	0.0207 (9)	0.0009 (8)
O2B	0.128 (2)	0.0528 (12)	0.0654 (13)	0.0362 (13)	0.0615 (14)	0.0211 (10)
O3B	0.0553 (10)	0.0428 (9)	0.0721 (12)	0.0245 (8)	0.0280 (9)	0.0123 (8)
O4B	0.126 (2)	0.100 (2)	0.0534 (13)	0.0370 (18)	0.0404 (15)	0.0133 (13)
O5B	0.122 (2)	0.119 (2)	0.0731 (15)	0.0732 (19)	0.0545 (16)	0.0567 (16)
O6A	0.123 (2)	0.0541 (13)	0.137 (3)	0.0198 (13)	0.080 (2)	0.0015 (14)
O7A	0.123 (2)	0.0541 (13)	0.137 (3)	0.0198 (13)	0.080 (2)	0.0015 (14)
O6B	0.123 (2)	0.0541 (13)	0.137 (3)	0.0198 (13)	0.080 (2)	0.0015 (14)
O7B	0.123 (2)	0.0541 (13)	0.137 (3)	0.0198 (13)	0.080 (2)	0.0015 (14)
N1B	0.0487 (11)	0.0368 (10)	0.0450 (11)	0.0152 (9)	0.0163 (9)	0.0070 (8)
N2B	0.0743 (17)	0.087 (2)	0.0550 (14)	0.0398 (15)	0.0343 (13)	0.0262 (14)
N3B	0.0766 (17)	0.0369 (12)	0.0908 (19)	0.0209 (12)	0.0430 (15)	0.0145 (12)
C1B	0.0467 (13)	0.0384 (12)	0.0545 (14)	0.0144 (10)	0.0239 (11)	0.0086 (10)
C2B	0.0450 (12)	0.0389 (12)	0.0475 (13)	0.0167 (10)	0.0208 (10)	0.0114 (10)
C3B	0.0479 (13)	0.0458 (13)	0.0495 (13)	0.0180 (11)	0.0229 (11)	0.0088 (10)
C4B	0.0588 (15)	0.0616 (16)	0.0507 (14)	0.0279 (13)	0.0291 (13)	0.0209 (12)
C5B	0.0689 (17)	0.0520 (15)	0.0729 (19)	0.0294 (14)	0.0420 (15)	0.0291 (14)
C6B	0.0562 (15)	0.0409 (13)	0.0667 (17)	0.0184 (11)	0.0306 (13)	0.0138 (12)

F1—C6	1.351 (3)	C12—H12B	0.9800
F2—C8	1.348 (3)	C12—H12C	0.9800
O1—C17	1.202 (4)	C13—C14	1.485 (4)
O2—C17	1.323 (4)	C13—H13A	0.9900
O2—H2	0.8400	C13—H13B	0.9900
O3—C3	1.258 (3)	C14—H14A	0.9900
N1—C1	1.343 (3)	C14—H14B	0.9900
N1—C9	1.397 (3)	C15—C16	1.499 (5)
N1—C15	1.492 (3)	C15—H15A	0.9900
N2—C7	1.381 (3)	C15—H15B	0.9900
N2—C10	1.455 (3)	C16—H16A	0.9800
N2—C14	1.460 (3)	C16—H16B	0.9800
N3—C13	1.490 (3)	C16—H16C	0.9800
N3—C11	1.504 (3)	O1B—C1B	1.248 (3)
N3—H3A	0.9200	O2B—N1B	1.221 (3)
N3—H3B	0.9200	O3B—N1B	1.226 (3)
C1—C2	1.351 (4)	O4B—N2B	1.218 (4)
C1—H1A	0.9500	O5B—N2B	1.227 (4)
C2—C3	1.422 (4)	O6A—N3B	1.219 (3)
C2—C17	1.489 (3)	O7A—N3B	1.2298 (19)
C3—C4	1.459 (3)	O6B—N3B	1.219 (5)
C4—C5	1.400 (4)	O7B—N3B	1.234 (2)
C4—C9	1.405 (3)	N1B—C2B	1.455 (3)
C5—C6	1.350 (4)	N2B—C4B	1.449 (4)
C5—H5A	0.9500	N3B—C6B	1.451 (3)
C6—C7	1.407 (4)	C1B—C2B	1.443 (3)
C7—C8	1.392 (3)	C1B—C6B	1.444 (4)
C8—C9	1.405 (3)	C2B—C3B	1.370 (4)
C10—C11	1.503 (4)	C3B—C4B	1.377 (4)
C10—H10A	0.9900	C3B—H3BA	0.9500
C10—H10B	0.9900	C4B—C5B	1.388 (4)
C11—C12	1.493 (4)	C5B—C6B	1.351 (4)
C11—H11A	1.0000	C5B—H5BA	0.9500
C12—H12A	0.9800
C17—O2—H2	109.5	C14—C13—N3	110.8 (2)
C1—N1—C9	119.0 (2)	C14—C13—H13A	109.5
C1—N1—C15	116.0 (2)	N3—C13—H13A	109.5
C9—N1—C15	125.02 (19)	C14—C13—H13B	109.5
C7—N2—C10	121.8 (2)	N3—C13—H13B	109.5
C7—N2—C14	122.7 (2)	H13A—C13—H13B	108.1
C10—N2—C14	112.8 (2)	N2—C14—C13	109.3 (2)
C13—N3—C11	112.07 (19)	N2—C14—H14A	109.8
C13—N3—H3A	109.2	C13—C14—H14A	109.8
C11—N3—H3A	109.2	N2—C14—H14B	109.8
C13—N3—H3B	109.2	C13—C14—H14B	109.8
C11—N3—H3B	109.2	H14A—C14—H14B	108.3
H3A—N3—H3B	107.9	N1—C15—C16	112.5 (2)
N1—C1—C2	124.9 (2)	N1—C15—H15A	109.1
N1—C1—H1A	117.5	C16—C15—H15A	109.1
C2—C1—H1A	117.5	N1—C15—H15B	109.1
C1—C2—C3	120.0 (2)	C16—C15—H15B	109.1
C1—C2—C17	118.2 (3)	H15A—C15—H15B	107.8
C3—C2—C17	121.8 (3)	C15—C16—H16A	109.5
O3—C3—C2	122.7 (2)	C15—C16—H16B	109.5
O3—C3—C4	121.5 (3)	H16A—C16—H16B	109.5
C2—C3—C4	115.8 (2)	C15—C16—H16C	109.5
C5—C4—C9	120.0 (2)	H16A—C16—H16C	109.5
C5—C4—C3	119.2 (2)	H16B—C16—H16C	109.5
C9—C4—C3	120.7 (2)	O1—C17—O2	121.1 (3)
C6—C5—C4	119.9 (2)	O1—C17—C2	124.3 (3)
C6—C5—H5A	120.1	O2—C17—C2	114.5 (3)
C4—C5—H5A	120.1	O2B—N1B—O3B	122.9 (2)
C5—C6—F1	119.3 (2)	O2B—N1B—C2B	118.9 (2)
C5—C6—C7	123.6 (2)	O3B—N1B—C2B	118.1 (2)
F1—C6—C7	117.2 (2)	O4B—N2B—O5B	123.5 (3)
N2—C7—C8	123.3 (2)	O4B—N2B—C4B	118.7 (3)
N2—C7—C6	121.4 (2)	O5B—N2B—C4B	117.9 (3)
C8—C7—C6	115.2 (2)	O6A—N3B—O7A	121.6 (3)
F2—C8—C7	116.6 (2)	O6B—N3B—O7B	119.2 (6)
F2—C8—C9	119.6 (2)	O6B—N3B—C6B	126.3 (5)
C7—C8—C9	123.8 (2)	O6A—N3B—C6B	117.5 (3)
N1—C9—C4	119.3 (2)	O7A—N3B—C6B	119.2 (3)
N1—C9—C8	123.4 (2)	O7B—N3B—C6B	114.5 (5)
C4—C9—C8	117.2 (2)	O1B—C1B—C2B	125.8 (2)
N2—C10—C11	111.5 (2)	O1B—C1B—C6B	123.3 (2)
N2—C10—H10A	109.3	C2B—C1B—C6B	110.8 (2)
C11—C10—H10A	109.3	C3B—C2B—C1B	124.9 (2)
N2—C10—H10B	109.3	C3B—C2B—N1B	117.3 (2)
C11—C10—H10B	109.3	C1B—C2B—N1B	117.8 (2)
H10A—C10—H10B	108.0	C2B—C3B—C4B	118.7 (2)
C12—C11—C10	114.0 (3)	C2B—C3B—H3BA	120.7
C12—C11—N3	110.5 (2)	C4B—C3B—H3BA	120.7
C10—C11—N3	108.1 (2)	C3B—C4B—C5B	121.3 (3)
C12—C11—H11A	108.0	C3B—C4B—N2B	119.0 (3)
C10—C11—H11A	108.0	C5B—C4B—N2B	119.7 (3)
N3—C11—H11A	108.0	C6B—C5B—C4B	118.5 (3)
C11—C12—H12A	109.5	C6B—C5B—H5BA	120.7
C11—C12—H12B	109.5	C4B—C5B—H5BA	120.7
H12A—C12—H12B	109.5	C5B—C6B—C1B	125.7 (3)
C11—C12—H12C	109.5	C5B—C6B—N3B	117.9 (3)
H12A—C12—H12C	109.5	C1B—C6B—N3B	116.4 (3)
H12B—C12—H12C	109.5
C9—N1—C1—C2	2.6 (4)	C13—N3—C11—C12	−179.5 (3)
C15—N1—C1—C2	−178.6 (2)	C13—N3—C11—C10	55.1 (3)
N1—C1—C2—C3	1.4 (4)	C11—N3—C13—C14	−57.0 (3)
N1—C1—C2—C17	−178.7 (2)	C7—N2—C14—C13	140.2 (3)
C1—C2—C3—O3	178.3 (2)	C10—N2—C14—C13	−57.9 (4)
C17—C2—C3—O3	−1.6 (4)	N3—C13—C14—N2	56.2 (3)
C1—C2—C3—C4	−2.2 (4)	C1—N1—C15—C16	−85.8 (3)
C17—C2—C3—C4	177.9 (2)	C9—N1—C15—C16	92.9 (3)
O3—C3—C4—C5	1.2 (4)	C1—C2—C17—O1	−0.1 (4)
C2—C3—C4—C5	−178.3 (2)	C3—C2—C17—O1	179.8 (3)
O3—C3—C4—C9	178.6 (2)	C1—C2—C17—O2	179.2 (3)
C2—C3—C4—C9	−0.9 (3)	C3—C2—C17—O2	−0.9 (4)
C9—C4—C5—C6	−0.3 (4)	O1B—C1B—C2B—C3B	173.3 (3)
C3—C4—C5—C6	177.1 (2)	C6B—C1B—C2B—C3B	−3.2 (4)
C4—C5—C6—F1	176.3 (2)	O1B—C1B—C2B—N1B	−4.6 (4)
C4—C5—C6—C7	−3.2 (4)	C6B—C1B—C2B—N1B	178.8 (2)
C10—N2—C7—C8	−129.4 (3)	O2B—N1B—C2B—C3B	142.1 (3)
C14—N2—C7—C8	30.8 (4)	O3B—N1B—C2B—C3B	−36.0 (3)
C10—N2—C7—C6	52.8 (4)	O2B—N1B—C2B—C1B	−39.8 (3)
C14—N2—C7—C6	−146.9 (3)	O3B—N1B—C2B—C1B	142.1 (2)
C5—C6—C7—N2	180.0 (2)	C1B—C2B—C3B—C4B	3.3 (4)
F1—C6—C7—N2	0.4 (4)	N1B—C2B—C3B—C4B	−178.8 (2)
C5—C6—C7—C8	2.0 (4)	C2B—C3B—C4B—C5B	−1.6 (4)
F1—C6—C7—C8	−177.5 (2)	C2B—C3B—C4B—N2B	177.8 (2)
N2—C7—C8—F2	8.0 (4)	O4B—N2B—C4B—C3B	2.6 (4)
C6—C7—C8—F2	−174.1 (2)	O5B—N2B—C4B—C3B	−177.9 (3)
N2—C7—C8—C9	−175.2 (2)	O4B—N2B—C4B—C5B	−178.0 (3)
C6—C7—C8—C9	2.7 (4)	O5B—N2B—C4B—C5B	1.6 (4)
C1—N1—C9—C4	−5.6 (3)	C3B—C4B—C5B—C6B	0.2 (4)
C15—N1—C9—C4	175.7 (2)	N2B—C4B—C5B—C6B	−179.2 (3)
C1—N1—C9—C8	171.8 (2)	C4B—C5B—C6B—C1B	−0.4 (5)
C15—N1—C9—C8	−6.9 (4)	C4B—C5B—C6B—N3B	179.7 (3)
C5—C4—C9—N1	−177.8 (2)	O1B—C1B—C6B—C5B	−174.9 (3)
C3—C4—C9—N1	4.8 (3)	C2B—C1B—C6B—C5B	1.8 (4)
C5—C4—C9—C8	4.6 (3)	O1B—C1B—C6B—N3B	5.0 (4)
C3—C4—C9—C8	−172.8 (2)	C2B—C1B—C6B—N3B	−178.3 (2)
F2—C8—C9—N1	−6.6 (4)	O6B—N3B—C6B—C5B	130.8 (9)
C7—C8—C9—N1	176.6 (2)	O6A—N3B—C6B—C5B	65.1 (5)
F2—C8—C9—C4	170.8 (2)	O7A—N3B—C6B—C5B	−129.3 (4)
C7—C8—C9—C4	−5.9 (4)	O7B—N3B—C6B—C5B	−48.8 (7)
C7—N2—C10—C11	−139.1 (3)	O6B—N3B—C6B—C1B	−49.1 (9)
C14—N2—C10—C11	58.8 (4)	O6A—N3B—C6B—C1B	−114.8 (4)
N2—C10—C11—C12	−178.6 (3)	O7A—N3B—C6B—C1B	50.8 (5)
N2—C10—C11—N3	−55.3 (3)	O7B—N3B—C6B—C1B	131.3 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.84	1.74	2.520 (3)	153
N3—H3A···O2i	0.92	2.09	2.984 (3)	164
N3—H3B···O1B	0.92	1.81	2.714 (3)	166
N3—H3B···O2B	0.92	2.52	2.993 (3)	113

CgI···CgJ	Cg···Cg (Å)	CgI Perp (Å)	Cgj Perp (Å)	Slippage (Å)
Cg1···Cg1i	3.6460 (14)	3.3385 (10)	3.3385 (10)	1.46 (6)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3	0.84	1.74	2.520 (3)	153
N3—H3A⋯O2i	0.92	2.09	2.984 (3)	164
N3—H3B⋯O1B	0.92	1.81	2.714 (3)	166
N3—H3B⋯O2B	0.92	2.52	2.993 (3)	113

Symmetry code: (i) .