Acta Cryst.(2004). E60, o1051±o1053 DOI: 10.1107/S1600536804011948 Liang-Cai Yuet al. C15H18FN4O3+Iÿ
o1051
organic papers
Acta Crystallographica Section E
Structure Reports
Online ISSN 1600-5368
Enoxacin hydroiodide
Liang-Cai Yu,a,bHong Liang,a,b*
Chun-Shan Zhou,aZhen-Feng
Chenband Yong Zhangc
aCollege of Chemistry and Chemical
Engineering, Central-South University, Changsha 410012, People's Republic of China, bCollege of Chemistry and Chemical
Engineering, Guangxi Normal University, Guilin 541004, People's Republic of China, and cCollege of Chemistry and Chemical
Engineering, Suzhou University, Suzhou 215006, People's Republic of China
Correspondence e-mail: [email protected]
Key indicators
Single-crystal X-ray study T= 193 K
Mean(C±C) = 0.005 AÊ Rfactor = 0.042 wRfactor = 0.078
Data-to-parameter ratio = 16.5
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2004 International Union of Crystallography Printed in Great Britain ± all rights reserved
The title compound, C15H18FN4O3+Iÿ, forms ionic crystals
consisting of protonated enoxacin cations, C15H18FN4O3+, and
Iÿanions. The naphthyridine system of the cation is essentially
planar, whereas the piperazine ring has a chair conformation; the enoxacin is protonated at the unsubstituted N atom of the piperazine ring. The carboxyl OH group forms an intramo-lecular hydrogen bond with the carbonyl O atom of the naphthyridine system, thus forming a six-membered pseudo-ring. The crystal packing is stabilized by±stacking of the naphthyridine rings and intermolecular hydrogen bonding involving the piperazine NÐH group, the carboxyl group of
the cation and the Iÿ anion, linking the residues of the
structure into in®nite chains running along the diagonal of the
acplane.
Comment
Enoxacin,
1-ethyl-6-¯uoro-1,4-dihydro-4-oxo-7-(1-piper-azinyl)-1,8-naphthyridine-3-carboxylic acid, is a synthetic antibacterial drug of the ¯uoroquinolone class, and is rapidly bactericidal against Gram-positive and -negative organisms
including Pseudomonas aeruginosa and Enterobacteriaceae
(Siporin & Towse, 1984). A number of such naphthyridine derivatives have been crystallographically characterized (Dattaet al., 1995); one of them,viz. nalidixic acid, has been studied several times (Achari & Neidle, 1976; Huber et al., 1980; Ohet al., 1986). However, as far as we are aware, the crystal structure of enoxacin has not been reported.
The ionic crystals of enoxacin of the title salt, (I), of enoxacin are composed of cations involving protonated quinolone groups and iodide anions (Fig. 1). Similar to what is observed in the structure of 6-chloro-1-ethyl-1,4-dihydro-4- oxo-7-(4-methyl-1-piperazinyl)-1,8-naphthyridine-3-carboxyl-ic acid (Dattaet al., 1995), the bicyclic naphthyridine system is essentially planar, whereas the piperazine ring has a chair conformation. The unsubstituted N atom of the piperazine ring (N4) is protonated, while the carboxyl group is not dissociated. The ethyl group plane (N1, C10 and C11) is almost orthogonal to the mean plane of the naphthyridine system; the corresponding dihedral angle is 80.57 (19). All the
organic papers
o1052
Liang-Cai Yuet al. C15H18FN4O3+Iÿ Acta Cryst.(2004). E60, o1051±o1053distances and angles within the rigid quinolone ring system and in the piperazine ring are similar to those found previously in related compounds (e.g. nalidixic acid and its derivatives; Achari & Neidle, 1976; Dattaet al., 1995; Huberet al., 1980; Ohet al., 1986).
The hydrogen bond O2ÐH2 O1, involving the carboxyl
OH group and the naphthyridine oxo atom, forms a six-membered pseudo-ring within the cation. The piperazine NH groups function as the donors of hydrogen bonds involving caboxyl O atoms and link neighbouring cations in the crystal structure; they also participate in hydrogen bonds with the Iÿ
anions (Table 2). Interionic hydrogen bonds link the residues in the structure of (I) into in®nite chains extending along the diagonal of theac plane of the unit cell (Fig. 2). The crystal
packing of (I) is also stabilized by ± stacking of the
napththyridine rings.
Experimental
Samples of 1.5 mmol of enoxacin (purchased from Fluka) and 1 mmol of PbI2were thoroughly mixed and placed in an autoclave. After
addition of 4 ml of EtOH and 12 ml of H2O (pH = 5.0), the autoclave
was heated at 373 K for 3 d to give light-yellow crystals of compound (I) in a 40% yield.
Crystal data C15H18FN4O3+Iÿ Mr= 448.23
Triclinic,P1
a= 6.9831 (17) AÊ
b= 10.235 (3) AÊ
c= 11.931 (3) AÊ
= 82.783 (11)
= 79.961 (11)
= 85.934 (12)
V= 832.0 (4) AÊ3
Z= 2
Dx= 1.789 Mg mÿ3
MoKradiation Cell parameters from 3760
re¯ections
= 3.2±27.5
= 1.96 mmÿ1 T= 193 (2) K Irregular, light yellow 0.200.110.07 mm
Data collection Rigaku Mercury CCD
diffractometer
!scans
Absorption correction: multi-scan (Jacobson, 1998)
Tmin= 0.696,Tmax= 0.875
9442 measured re¯ections
3753 independent re¯ections 3401 re¯ections withI> 2(I)
Rint= 0.037
max= 27.5 h=ÿ7!9
k=ÿ13!13
l=ÿ15!14 Re®nement
Re®nement onF2 R[F2> 2(F2)] = 0.042 wR(F2) = 0.078 S= 1.18 3753 re¯ections 227 parameters
H atoms treated by a mixture of independent and constrained re®nement
w= 1/[2(F
o2) + (0.0167P)2
+ 1.7702P]
whereP= (Fo2+ 2Fc2)/3
(/)max< 0.001
max= 0.55 e AÊÿ3
min=ÿ0.64 e AÊÿ3
Table 1
Selected bond distances (AÊ).
C1ÐC3 1.480 (5) C2ÐC3 1.376 (5) C3ÐC4 1.432 (5) C4ÐC9 1.432 (5) C5ÐC6 1.351 (5) C5ÐC9 1.411 (5) C6ÐC7 1.420 (5) C8ÐC9 1.395 (5) C10ÐC11 1.509 (5) C12ÐC13 1.507 (6) C14ÐC15 1.510 (6) F1ÐC6 1.369 (4) O1ÐC4 1.275 (4)
O2ÐC1 1.326 (5) O3ÐC1 1.214 (5) N1ÐC2 1.340 (5) N1ÐC8 1.398 (5) N1ÐC10 1.488 (5) N2ÐC8 1.331 (5) N2ÐC7 1.339 (5) N3ÐC7 1.365 (5) N3ÐC12 1.466 (5) N3ÐC15 1.467 (5) N4ÐC13 1.490 (5) N4ÐC14 1.491 (6)
Table 2
Hydrogen-bonding geometry (AÊ,).
DÐH A DÐH H A D A DÐH A
O2ÐH2 O1 0.84 1.65 2.442 (4) 156 N4ÐH4B I1i 0.84 (5) 2.61 (5) 3.421 (4) 163 (4)
N4ÐH4A O2ii 0.91 (6) 2.02 (6) 2.880 (5) 156 (5)
N4ÐH4A O3ii 0.91 (6) 2.39 (6) 3.182 (5) 145 (5)
Symmetry codes: (i) 1ÿx;1ÿy;2ÿz; (ii)xÿ1;y;1z.
H atoms bonded to C and O atoms were positioned geometrically; they were treated as riding, with CÐH = 0.93 AÊ, OÐH = 0.84 AÊ and
Uiso(H) = 1.2eq(C) or 1.5eq(O). H atoms bound to atom N4 were
located in a difference map and re®ned isotropically; NÐH = 0.84 (5) and 0.91 (6) AÊ.
Data collection: CrystalClear (Rigaku, 1999); cell re®nement:
CrystalClear; data reduction:CrystalStructure(Rigaku and Rigaku/ MSC, 2000); program(s) used to solve structure:SHELXS97 (Shel-drick, 1997); program(s) used to re®ne structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1994); software used to prepare material for publication:SHELXTL.
The authors thank the Youth Science Foundation of Guangxi, the Natural Science Foundation of Guangxi, and the Project of One Hundred Persons Plan of Guangxi Universities of the People's Republic of China, as well as the Teaching and Research Award Program for Outstanding Young Teachers in
Figure 2
A packing diagram for compound (I). Dashed lines indicate hydrogen bonds.
Figure 1
Higher Education Institutions of the Chinese Ministry of Education.
References
Achari, A. & Neidle, S. (1976).Acta Cryst.B32, 600±602.
Datta, M., Hannan, S. S. & Talukdar, A. N. (1995).Acta Cryst.C51, 978±980. Huber, C. P., Gowda, D. S. S. & Acharya, K. R. (1980).Acta Cryst.B36, 497±
499.
Jacobson, R. (1998). Private communication to Rigaku. Rigaku Corporation, Tokyo, Japan.
Oh, I.-K., Ko, T.-S., Lee, C.-B., Suh, J.-I. & Suh, I.-H. (1986).Chung.J. Sci.13, 51±58.
Rigaku & Rigaku/MSC (2000). CrystalStructure. Rigaku/MSC, 9009 New Trails Drive, The Woodlands, TX 77381, USA, and Rigaku Corporation, Tokyo, Japan.
Rigaku (1999).CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of GoÈttingen, Germany.
Siemens (1994). XSCANS (Version 2.10b) and SHELXTL. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Siporin, C. & Towse, G. (1984).J. Antimicrob. Chemother.14, Suppl. C, 47± 55.
supporting information
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Acta Cryst. (2004). E60, o1051–o1053
supporting information
Acta Cryst. (2004). E60, o1051–o1053 [https://doi.org/10.1107/S1600536804011948]
Enoxacin hydroiodide
Liang-Cai Yu, Hong Liang, Chun-Shan Zhou, Zhen-Feng Chen and Yong Zhang
(I)
Crystal data
C15H18FN4O3+·I−
Mr = 448.23
Triclinic, P1 Hall symbol: -P 1
a = 6.9831 (17) Å
b = 10.235 (3) Å
c = 11.931 (3) Å
α = 82.783 (11)°
β = 79.961 (11)°
γ = 85.934 (12)°
V = 832.0 (4) Å3
Z = 2
F(000) = 444
Dx = 1.789 Mg m−3
Mo Kα radiation, λ = 0.71070 Å Cell parameters from 3760 reflections
θ = 3.2–27.5°
µ = 1.96 mm−1
T = 193 K
Irregular, light yellow 0.20 × 0.11 × 0.07 mm
Data collection
Rigaku Mercury CCD diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
Detector resolution: 7.31 pixels mm-1
ω scans
Absorption correction: multi-scan (Jacobson, 1998)
Tmin = 0.696, Tmax = 0.875
9442 measured reflections 3753 independent reflections 3401 reflections with I > 2σ(I)′
Rint = 0.037
θmax = 27.5°, θmin = 3.2°
h = −7→9
k = −13→13
l = −15→14
Refinement
Refinement on F2 Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.042
wR(F2) = 0.078
S = 1.18 3753 reflections 227 parameters 0 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H atoms treated by a mixture of independent and constrained refinement
w = 1/[σ2(F
o2) + (0.0167P)2 + 1.7702P] where P = (Fo2 + 2Fc2)/3
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Acta Cryst. (2004). E60, o1051–o1053 Special details
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.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq
I1 0.70806 (4) 0.55328 (3) 0.77263 (2) 0.02814 (9)
F1 0.6576 (3) 0.9896 (3) 0.77860 (19) 0.0351 (6)
O1 0.9380 (4) 0.9109 (3) 0.3722 (2) 0.0274 (6)
O2 0.9727 (4) 0.8435 (3) 0.1801 (2) 0.0333 (7)
H2 0.9938 0.8720 0.2396 0.050*
O3 0.7482 (5) 0.7337 (4) 0.1287 (3) 0.0478 (9)
N1 0.4069 (4) 0.7437 (3) 0.4558 (3) 0.0187 (6)
N2 0.3579 (4) 0.8095 (3) 0.6379 (2) 0.0181 (6)
N3 0.2833 (5) 0.8713 (3) 0.8195 (3) 0.0263 (7)
N4 0.1901 (6) 0.6841 (4) 1.0144 (3) 0.0296 (8)
C2 0.5152 (5) 0.7386 (4) 0.3518 (3) 0.0212 (8)
H1 0.4663 0.6948 0.2979 0.025*
C3 0.6934 (5) 0.7937 (4) 0.3192 (3) 0.0202 (8)
C4 0.7735 (5) 0.8584 (3) 0.3988 (3) 0.0195 (7)
C9 0.6575 (5) 0.8610 (3) 0.5101 (3) 0.0184 (7)
C8 0.4758 (5) 0.8058 (3) 0.5377 (3) 0.0176 (7)
C5 0.7180 (5) 0.9236 (4) 0.5959 (3) 0.0215 (8)
H6 0.8401 0.9633 0.5825 0.026*
C6 0.5979 (6) 0.9257 (4) 0.6976 (3) 0.0226 (8)
C7 0.4142 (5) 0.8677 (3) 0.7204 (3) 0.0192 (7)
C1 0.8033 (6) 0.7866 (4) 0.2020 (3) 0.0300 (9)
C10 0.2179 (5) 0.6787 (4) 0.4870 (3) 0.0225 (8)
H10A 0.1672 0.6687 0.4163 0.027*
H10B 0.1226 0.7356 0.5330 0.027*
C11 0.2374 (6) 0.5451 (4) 0.5547 (3) 0.0261 (9)
H11A 0.3096 0.4831 0.5045 0.039*
H11B 0.1076 0.5131 0.5857 0.039*
H11C 0.3076 0.5522 0.6178 0.039*
C12 0.1057 (6) 0.7981 (4) 0.8363 (4) 0.0311 (10)
H12A 0.0722 0.7867 0.7609 0.037*
H12B −0.0038 0.8484 0.8787 0.037*
C13 0.1354 (6) 0.6649 (4) 0.9025 (3) 0.0296 (9)
H13A 0.0140 0.6167 0.9156 0.036*
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Acta Cryst. (2004). E60, o1051–o1053
C14 0.3639 (6) 0.7647 (4) 1.0016 (4) 0.0322 (10)
H14A 0.4805 0.7163 0.9640 0.039*
H14B 0.3870 0.7810 1.0781 0.039*
C15 0.3303 (7) 0.8943 (4) 0.9304 (3) 0.0324 (10)
H15A 0.2218 0.9463 0.9718 0.039*
H15B 0.4487 0.9455 0.9178 0.039*
H4A 0.091 (9) 0.725 (6) 1.060 (5) 0.067 (18)*
H4B 0.212 (7) 0.614 (5) 1.056 (4) 0.038 (14)*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
I1 0.03270 (15) 0.02672 (14) 0.02515 (14) 0.00166 (10) −0.00684 (10) −0.00252 (10)
F1 0.0350 (14) 0.0513 (16) 0.0232 (12) −0.0159 (12) −0.0041 (10) −0.0146 (11)
O1 0.0217 (14) 0.0316 (15) 0.0257 (14) −0.0063 (11) 0.0033 (11) 0.0014 (12)
O2 0.0341 (17) 0.0388 (18) 0.0227 (15) −0.0037 (13) 0.0083 (13) −0.0048 (13)
O3 0.050 (2) 0.072 (3) 0.0233 (16) −0.0148 (18) 0.0045 (15) −0.0189 (16)
N1 0.0200 (16) 0.0184 (15) 0.0179 (15) −0.0019 (12) −0.0022 (12) −0.0032 (12)
N2 0.0195 (15) 0.0184 (15) 0.0153 (15) −0.0020 (12) −0.0006 (12) −0.0002 (12)
N3 0.0263 (18) 0.0333 (19) 0.0187 (16) −0.0029 (14) 0.0001 (14) −0.0046 (14)
N4 0.033 (2) 0.030 (2) 0.0210 (18) 0.0032 (16) −0.0001 (16) 0.0056 (16)
C2 0.028 (2) 0.0204 (18) 0.0150 (17) 0.0034 (15) −0.0034 (15) −0.0019 (15)
C3 0.0229 (19) 0.0189 (18) 0.0172 (18) 0.0000 (15) −0.0004 (15) −0.0003 (15)
C4 0.0179 (18) 0.0167 (17) 0.0210 (18) 0.0017 (14) 0.0003 (15) 0.0020 (15)
C9 0.0202 (18) 0.0155 (17) 0.0174 (17) 0.0002 (14) −0.0008 (14) 0.0020 (14)
C8 0.0215 (18) 0.0128 (16) 0.0176 (17) 0.0011 (14) −0.0047 (15) 0.0026 (14)
C5 0.0219 (19) 0.0200 (18) 0.0214 (19) −0.0041 (15) −0.0027 (15) 0.0026 (15)
C6 0.027 (2) 0.0215 (19) 0.0200 (18) −0.0028 (15) −0.0041 (16) −0.0024 (15)
C7 0.0226 (19) 0.0153 (17) 0.0182 (18) 0.0006 (14) −0.0030 (15) 0.0023 (14)
C1 0.033 (2) 0.031 (2) 0.022 (2) 0.0030 (18) 0.0012 (18) −0.0001 (18)
C10 0.0171 (18) 0.028 (2) 0.0231 (19) −0.0049 (15) −0.0014 (15) −0.0062 (16)
C11 0.026 (2) 0.026 (2) 0.025 (2) −0.0079 (16) 0.0001 (17) −0.0011 (17)
C12 0.020 (2) 0.048 (3) 0.023 (2) −0.0005 (18) 0.0017 (16) 0.0004 (19)
C13 0.025 (2) 0.039 (2) 0.025 (2) −0.0061 (18) −0.0011 (17) −0.0042 (18)
C14 0.032 (2) 0.044 (3) 0.021 (2) −0.0043 (19) −0.0025 (17) −0.0049 (19)
C15 0.039 (2) 0.041 (3) 0.0182 (19) −0.011 (2) 0.0024 (18) −0.0115 (18)
Geometric parameters (Å, º)
C1—C3 1.480 (5) N3—C12 1.466 (5)
C2—C3 1.376 (5) N3—C15 1.467 (5)
C3—C4 1.432 (5) N4—C13 1.490 (5)
C4—C9 1.432 (5) N4—C14 1.491 (6)
C5—C6 1.351 (5) N4—H4A 0.91 (6)
C5—C9 1.411 (5) N4—H4B 0.84 (5)
C6—C7 1.420 (5) C2—H1 0.9500
C8—C9 1.395 (5) C5—H6 0.9500
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Acta Cryst. (2004). E60, o1051–o1053
C12—C13 1.507 (6) C10—H10B 0.9900
C14—C15 1.510 (6) C11—H11A 0.9800
F1—C6 1.369 (4) C11—H11B 0.9800
O1—C4 1.275 (4) C11—H11C 0.9800
O2—C1 1.326 (5) C12—H12A 0.9900
O2—H2 0.8400 C12—H12B 0.9900
O3—C1 1.214 (5) C13—H13A 0.9900
N1—C2 1.340 (5) C13—H13B 0.9900
N1—C8 1.398 (5) C14—H14A 0.9900
N1—C10 1.488 (5) C14—H14B 0.9900
N2—C8 1.331 (5) C15—H15A 0.9900
N2—C7 1.339 (5) C15—H15B 0.9900
N3—C7 1.365 (5)
C1—O2—H2 109.5 O3—C1—C3 124.6 (4)
C2—N1—C8 119.8 (3) O2—C1—C3 115.1 (4)
C2—N1—C10 120.8 (3) N1—C10—C11 112.1 (3)
C8—N1—C10 119.4 (3) N1—C10—H10A 109.2
C8—N2—C7 119.4 (3) C11—C10—H10A 109.2
C7—N3—C12 119.7 (3) N1—C10—H10B 109.2
C7—N3—C15 125.3 (3) C11—C10—H10B 109.2
C12—N3—C15 110.4 (3) H10A—C10—H10B 107.9
C13—N4—C14 113.0 (3) C10—C11—H11A 109.5
C13—N4—H4A 112 (4) C10—C11—H11B 109.5
C14—N4—H4A 107 (4) H11A—C11—H11B 109.5
C13—N4—H4B 115 (3) C10—C11—H11C 109.5
C14—N4—H4B 107 (3) H11A—C11—H11C 109.5
H4A—N4—H4B 103 (5) H11B—C11—H11C 109.5
N1—C2—C3 123.4 (3) N3—C12—C13 110.1 (3)
N1—C2—H1 118.3 N3—C12—H12A 109.6
C3—C2—H1 118.3 C13—C12—H12A 109.6
C2—C3—C4 119.9 (3) N3—C12—H12B 109.6
C2—C3—C1 120.4 (3) C13—C12—H12B 109.6
C4—C3—C1 119.7 (3) H12A—C12—H12B 108.2
O1—C4—C3 122.0 (3) N4—C13—C12 108.8 (3)
O1—C4—C9 122.0 (3) N4—C13—H13A 109.9
C3—C4—C9 116.0 (3) C12—C13—H13A 109.9
C8—C9—C5 116.7 (3) N4—C13—H13B 109.9
C8—C9—C4 121.6 (3) C12—C13—H13B 109.9
C5—C9—C4 121.7 (3) H13A—C13—H13B 108.3
N2—C8—C9 124.5 (3) N4—C14—C15 109.5 (3)
N2—C8—N1 116.2 (3) N4—C14—H14A 109.8
C9—C8—N1 119.3 (3) C15—C14—H14A 109.8
C6—C5—C9 118.3 (3) N4—C14—H14B 109.8
C6—C5—H6 120.9 C15—C14—H14B 109.8
C9—C5—H6 120.9 H14A—C14—H14B 108.2
C5—C6—F1 117.3 (3) N3—C15—C14 110.3 (3)
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Acta Cryst. (2004). E60, o1051–o1053
F1—C6—C7 120.4 (3) C14—C15—H15A 109.6
N2—C7—N3 116.2 (3) N3—C15—H15B 109.6
N2—C7—C6 118.8 (3) C14—C15—H15B 109.6
N3—C7—C6 125.0 (3) H15A—C15—H15B 108.1
O3—C1—O2 120.3 (4)
C8—N1—C2—C3 −1.0 (5) C9—C5—C6—C7 −0.2 (6)
C10—N1—C2—C3 −178.2 (3) C8—N2—C7—N3 178.1 (3)
N1—C2—C3—C4 1.2 (5) C8—N2—C7—C6 1.0 (5)
N1—C2—C3—C1 −178.8 (3) C12—N3—C7—N2 8.2 (5)
C2—C3—C4—O1 −179.9 (3) C15—N3—C7—N2 161.6 (4)
C1—C3—C4—O1 0.1 (5) C12—N3—C7—C6 −174.9 (3)
C2—C3—C4—C9 −0.1 (5) C15—N3—C7—C6 −21.5 (6)
C1—C3—C4—C9 179.9 (3) C5—C6—C7—N2 −0.4 (5)
O1—C4—C9—C8 178.6 (3) F1—C6—C7—N2 178.0 (3)
C3—C4—C9—C8 −1.3 (5) C5—C6—C7—N3 −177.2 (4)
O1—C4—C9—C5 1.0 (5) F1—C6—C7—N3 1.2 (6)
C3—C4—C9—C5 −178.9 (3) C2—C3—C1—O3 −0.3 (6)
C7—N2—C8—C9 −1.1 (5) C4—C3—C1—O3 179.8 (4)
C7—N2—C8—N1 −179.9 (3) C2—C3—C1—O2 179.7 (3)
C5—C9—C8—N2 0.5 (5) C4—C3—C1—O2 −0.3 (5)
C4—C9—C8—N2 −177.2 (3) C2—N1—C10—C11 98.1 (4)
C5—C9—C8—N1 179.3 (3) C8—N1—C10—C11 −79.1 (4)
C4—C9—C8—N1 1.5 (5) C7—N3—C12—C13 95.2 (4)
C2—N1—C8—N2 178.4 (3) C15—N3—C12—C13 −61.9 (4)
C10—N1—C8—N2 −4.3 (5) C14—N4—C13—C12 −55.4 (5)
C2—N1—C8—C9 −0.4 (5) N3—C12—C13—N4 58.0 (4)
C10—N1—C8—C9 176.9 (3) C13—N4—C14—C15 54.5 (5)
C8—C9—C5—C6 0.1 (5) C7—N3—C15—C14 −94.9 (5)
C4—C9—C5—C6 177.8 (3) C12—N3—C15—C14 60.6 (4)
C9—C5—C6—F1 −178.6 (3) N4—C14—C15—N3 −55.8 (5)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
O2—H2···O1 0.84 1.65 2.442 (4) 156
N4—H4B···I1i 0.84 (5) 2.61 (5) 3.421 (4) 163 (4)
N4—H4A···O2ii 0.91 (6) 2.02 (6) 2.880 (5) 156 (5)
N4—H4A···O3ii 0.91 (6) 2.39 (6) 3.182 (5) 145 (5)
