Crystal structure of (RS)-4-(3-carb­oxy-1-ethyl-6,8-di­fluoro-4-oxo-1,4-di­hydro­quinolin-7-yl)-2-methyl­piperazin-1-ium 3-carb­oxy-5-fluoro­benzoate

Reaction of lomefloxacin [(RS)-4-(3-carb­oxy-1-ethyl-6,8-di­fluoro-4-oxo-1,4-di­hydro­quinolin-7-yl)-2-methyl­piperazine, Lf] with 5-fluoro­isophthalic acid leads to a charge-assistant hydrogen-bonding network between HLf⁺ cations and 3-carb­oxy-5-fluoro­benzoate anions.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.054
• wR factor = 0.161
• Data-to-parameter ratio = 17.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C13      --C14      .        5.9 s.u.
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.4 Note
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.3 Note
PLAT480_ALERT_4_C Long H...A H-Bond Reported H21      ..O4       .       2.61 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2A      ..F3       .       2.57 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      7.096 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          4 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          1 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )         8% Note
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          3 Note
PLAT728_ALERT_1_G D-H..A  Calc      170.00, Rep      166.50 Dev...       3.50 Degree
              O5      -H5      -O7         1.555  1.555  4.565     #  124 Check
PLAT793_ALERT_4_G Model has Chirality at C1          (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C1'         (Centro SPGR)          S Verify
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        879 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         14 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  10 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   7 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

(RS)-4-(3-Carboxy-1-ethyl-6,8-difluoro-4-oxo-1,4-dihydroquinolin-7-yl)-2-methylpiperazin-1-ium 3-carboxy-5-fluorobenzoate

Crystal data

C17H20F2N3O3^+·C8H4FO4^−	F(000) = 1112
Mr = 535.47	Dx = 1.491 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.4324 (12) Å	Cell parameters from 5522 reflections
b = 16.5656 (19) Å	θ = 2.2–29.9°
c = 14.0448 (17) Å	µ = 0.13 mm^−1
β = 100.707 (3)°	T = 296 K
V = 2384.9 (5) Å^3	Block, colorless
Z = 4	0.22 × 0.20 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer	4335 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.035
Absorption correction: multi-scan (SADABS; Bruker, 2010)	θmax = 30.4°, θmin = 1.9°
Tmin = 0.970, Tmax = 0.980	h = −14→14
16570 measured reflections	k = −23→21
6292 independent reflections	l = −19→13

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.054	H-atom parameters constrained
wR(F^2) = 0.161	w = 1/[σ^2(Fo^2) + (0.085P)^2 + 0.686P] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max < 0.001
6292 reflections	Δρmax = 0.29 e Å^−3
358 parameters	Δρmin = −0.28 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C2	0.2703 (2)	0.12846 (10)	0.77391 (12)	0.0390 (4)
H2A	0.1793	0.1429	0.7531	0.047*
H2B	0.3232	0.1710	0.7536	0.047*
C3	0.21645 (19)	−0.01366 (11)	0.75432 (12)	0.0385 (4)
H3A	0.2383	−0.0636	0.7249	0.046*
H3B	0.1251	−0.0021	0.7299	0.046*
C4	0.23908 (19)	−0.02326 (11)	0.86352 (12)	0.0391 (4)
H4A	0.1800	−0.0637	0.8804	0.047*
H4B	0.3277	−0.0416	0.8868	0.047*
C1	0.30073 (19)	0.12083 (11)	0.88315 (12)	0.0398 (4)	0.645 (5)
H1	0.3925	0.1055	0.9030	0.048*	0.645 (5)
C5	0.2784 (4)	0.1988 (2)	0.9320 (2)	0.0587 (11)	0.645 (5)
H5A	0.2890	0.1903	1.0006	0.088*	0.645 (5)
H5B	0.1915	0.2177	0.9074	0.088*	0.645 (5)
H5C	0.3403	0.2383	0.9191	0.088*	0.645 (5)
C1'	0.30073 (19)	0.12083 (11)	0.88315 (12)	0.0398 (4)	0.355 (5)
H1'	0.2728	0.1712	0.9098	0.048*	0.355 (5)
C5'	0.4401 (7)	0.1112 (5)	0.9223 (4)	0.064 (2)	0.355 (5)
H5'1	0.4858	0.1593	0.9101	0.096*	0.355 (5)
H5'2	0.4734	0.0660	0.8917	0.096*	0.355 (5)
H5'3	0.4525	0.1020	0.9909	0.096*	0.355 (5)
C6	0.32692 (16)	0.05742 (10)	0.63571 (11)	0.0314 (3)
C7	0.25702 (16)	0.02250 (11)	0.55222 (12)	0.0348 (4)
C8	0.29167 (16)	0.02851 (11)	0.46031 (11)	0.0360 (4)
C9	0.39760 (17)	0.07840 (11)	0.45220 (12)	0.0375 (4)
C10	0.46920 (18)	0.11506 (11)	0.53468 (13)	0.0378 (4)
H10	0.5396	0.1481	0.5295	0.045*
C11	0.43600 (17)	0.10242 (11)	0.62229 (12)	0.0354 (4)
C12	0.4354 (2)	0.09342 (13)	0.35878 (13)	0.0468 (5)
C13	0.3573 (2)	0.05467 (14)	0.27828 (13)	0.0511 (5)
C14	0.2580 (2)	0.00583 (15)	0.29119 (13)	0.0533 (6)
H14	0.2103	−0.0191	0.2366	0.064*
C15	0.3820 (3)	0.06630 (18)	0.17808 (15)	0.0690 (8)
C16	0.12118 (19)	−0.07161 (18)	0.37829 (15)	0.0621 (7)
H16A	0.0763	−0.0816	0.3124	0.075*
H16B	0.0576	−0.0514	0.4148	0.075*
C17	0.1759 (2)	−0.14920 (18)	0.4221 (2)	0.0711 (8)
H17A	0.2399	−0.1692	0.3869	0.107*
H17B	0.1070	−0.1880	0.4192	0.107*
H17C	0.2161	−0.1403	0.4885	0.107*
C18	0.15025 (16)	0.22254 (10)	0.33449 (12)	0.0331 (4)
C19	0.25938 (16)	0.27147 (10)	0.33760 (12)	0.0331 (4)
H19	0.2883	0.2841	0.2806	0.040*
C20	0.32544 (16)	0.30154 (10)	0.42577 (11)	0.0325 (3)
C21	0.28309 (17)	0.28192 (11)	0.51078 (12)	0.0352 (4)
H21	0.3271	0.3008	0.5703	0.042*
C22	0.17472 (17)	0.23394 (12)	0.50507 (12)	0.0389 (4)
C23	0.10696 (17)	0.20350 (11)	0.41930 (12)	0.0374 (4)
H23	0.0340	0.1710	0.4182	0.045*
C24	0.07378 (18)	0.18979 (11)	0.24192 (13)	0.0398 (4)
C25	0.44349 (18)	0.35535 (11)	0.43029 (12)	0.0390 (4)
F1	0.14586 (10)	−0.01682 (8)	0.56051 (8)	0.0542 (3)
F2	0.51182 (11)	0.13417 (7)	0.70199 (8)	0.0502 (3)
F3	0.13353 (12)	0.21463 (9)	0.58853 (8)	0.0600 (4)
N1	0.21749 (14)	0.05481 (9)	0.91112 (10)	0.0366 (3)
H1A	0.2354	0.0485	0.9751	0.044*
H1B	0.1339	0.0688	0.8945	0.044*
N2	0.29693 (15)	0.05198 (8)	0.72827 (10)	0.0349 (3)
N3	0.22256 (15)	−0.00954 (12)	0.37700 (10)	0.0466 (4)
O1	0.52996 (17)	0.13801 (11)	0.35126 (11)	0.0634 (4)
O2	0.4753 (2)	0.11777 (15)	0.16934 (12)	0.0864 (6)
H2	0.5061	0.1367	0.2226	0.130*
O3	0.3194 (2)	0.03032 (14)	0.10876 (11)	0.0906 (7)
O4	−0.03217 (17)	0.16034 (13)	0.23770 (11)	0.0770 (6)
O5	0.13137 (13)	0.19749 (9)	0.16727 (9)	0.0483 (3)
H5	0.0852	0.1778	0.1192	0.073*
O6	0.46630 (13)	0.38375 (9)	0.35255 (9)	0.0500 (4)
O7	0.51218 (16)	0.36907 (10)	0.51142 (10)	0.0619 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.0599 (11)	0.0327 (9)	0.0257 (8)	0.0003 (8)	0.0111 (8)	−0.0032 (7)
C3	0.0511 (10)	0.0366 (9)	0.0280 (8)	−0.0052 (8)	0.0074 (7)	−0.0045 (7)
C4	0.0526 (10)	0.0355 (9)	0.0297 (8)	0.0002 (8)	0.0089 (7)	0.0023 (7)
C1	0.0533 (10)	0.0421 (10)	0.0244 (8)	−0.0045 (8)	0.0079 (7)	−0.0076 (7)
C5	0.087 (3)	0.052 (2)	0.0429 (18)	−0.0161 (17)	0.0286 (17)	−0.0244 (15)
C1'	0.0533 (10)	0.0421 (10)	0.0244 (8)	−0.0045 (8)	0.0079 (7)	−0.0076 (7)
C5'	0.066 (4)	0.091 (5)	0.033 (3)	−0.029 (4)	0.006 (3)	0.000 (3)
C6	0.0390 (8)	0.0346 (8)	0.0204 (7)	0.0060 (7)	0.0047 (6)	−0.0019 (6)
C7	0.0321 (8)	0.0470 (10)	0.0252 (8)	0.0041 (7)	0.0050 (6)	−0.0063 (7)
C8	0.0358 (8)	0.0502 (10)	0.0201 (7)	0.0152 (7)	0.0005 (6)	−0.0052 (7)
C9	0.0411 (9)	0.0482 (10)	0.0240 (8)	0.0183 (8)	0.0084 (7)	0.0030 (7)
C10	0.0411 (9)	0.0401 (9)	0.0337 (9)	0.0066 (7)	0.0111 (7)	0.0017 (7)
C11	0.0418 (9)	0.0362 (9)	0.0262 (8)	0.0040 (7)	0.0011 (7)	−0.0031 (7)
C12	0.0539 (11)	0.0578 (12)	0.0312 (9)	0.0269 (10)	0.0143 (8)	0.0094 (8)
C13	0.0613 (12)	0.0703 (14)	0.0233 (8)	0.0313 (11)	0.0119 (8)	0.0059 (8)
C14	0.0551 (12)	0.0824 (15)	0.0194 (8)	0.0299 (11)	−0.0009 (8)	−0.0088 (9)
C15	0.0890 (18)	0.0935 (19)	0.0263 (10)	0.0476 (16)	0.0155 (11)	0.0118 (11)
C16	0.0340 (10)	0.113 (2)	0.0366 (10)	0.0000 (11)	0.0000 (8)	−0.0361 (12)
C17	0.0545 (13)	0.0898 (19)	0.0727 (16)	−0.0240 (13)	0.0213 (12)	−0.0368 (15)
C18	0.0350 (8)	0.0344 (8)	0.0284 (8)	0.0011 (7)	0.0014 (7)	0.0012 (6)
C19	0.0377 (8)	0.0372 (9)	0.0236 (7)	0.0006 (7)	0.0036 (6)	0.0052 (6)
C20	0.0367 (8)	0.0331 (8)	0.0262 (8)	0.0031 (7)	0.0016 (6)	0.0046 (6)
C21	0.0406 (9)	0.0405 (9)	0.0225 (7)	0.0050 (7)	0.0010 (6)	0.0017 (6)
C22	0.0399 (9)	0.0517 (11)	0.0261 (8)	0.0057 (8)	0.0091 (7)	0.0082 (7)
C23	0.0345 (8)	0.0428 (10)	0.0344 (9)	0.0006 (7)	0.0054 (7)	0.0068 (7)
C24	0.0452 (10)	0.0417 (10)	0.0307 (8)	−0.0073 (8)	0.0023 (7)	0.0016 (7)
C25	0.0415 (9)	0.0446 (10)	0.0271 (8)	−0.0048 (8)	−0.0038 (7)	0.0082 (7)
F1	0.0424 (6)	0.0885 (9)	0.0324 (6)	−0.0148 (6)	0.0091 (5)	−0.0211 (6)
F2	0.0567 (7)	0.0588 (7)	0.0332 (6)	−0.0169 (5)	0.0034 (5)	−0.0103 (5)
F3	0.0566 (7)	0.0962 (10)	0.0305 (6)	−0.0063 (7)	0.0170 (5)	0.0108 (6)
N1	0.0432 (8)	0.0460 (8)	0.0210 (6)	0.0023 (6)	0.0072 (6)	−0.0016 (6)
N2	0.0506 (8)	0.0330 (7)	0.0219 (6)	−0.0036 (6)	0.0087 (6)	−0.0057 (5)
N3	0.0396 (8)	0.0754 (12)	0.0227 (7)	0.0143 (8)	0.0002 (6)	−0.0126 (7)
O1	0.0681 (10)	0.0823 (11)	0.0460 (8)	0.0089 (9)	0.0270 (8)	0.0126 (8)
O2	0.1021 (15)	0.1232 (18)	0.0419 (9)	0.0267 (13)	0.0340 (10)	0.0196 (10)
O3	0.1254 (16)	0.1244 (17)	0.0205 (7)	0.0381 (14)	0.0098 (9)	0.0027 (9)
O4	0.0699 (10)	0.1159 (15)	0.0427 (8)	−0.0525 (11)	0.0038 (8)	−0.0062 (9)
O5	0.0497 (8)	0.0640 (9)	0.0298 (6)	−0.0099 (6)	0.0036 (6)	−0.0103 (6)
O6	0.0497 (8)	0.0677 (9)	0.0292 (6)	−0.0176 (7)	−0.0014 (6)	0.0136 (6)
O7	0.0681 (9)	0.0778 (11)	0.0312 (7)	−0.0309 (8)	−0.0134 (7)	0.0147 (7)

Geometric parameters (Å, º)

C2—N2	1.469 (2)	C12—O1	1.252 (3)
C2—C1	1.513 (2)	C12—C13	1.419 (3)
C2—C1'	1.513 (2)	C13—C14	1.353 (3)
C2—H2A	0.9700	C13—C15	1.490 (3)
C2—H2B	0.9700	C14—N3	1.349 (2)
C3—N2	1.461 (2)	C14—H14	0.9300
C3—C4	1.516 (2)	C15—O3	1.222 (4)
C3—H3A	0.9700	C15—O2	1.317 (4)
C3—H3B	0.9700	C16—N3	1.478 (3)
C4—N1	1.492 (2)	C16—C17	1.492 (4)
C4—H4A	0.9700	C16—H16A	0.9700
C4—H4B	0.9700	C16—H16B	0.9700
C1—N1	1.494 (2)	C17—H17A	0.9600
C1—C5	1.501 (3)	C17—H17B	0.9600
C1—H1	0.9800	C17—H17C	0.9600
C5—H5A	0.9600	C18—C23	1.386 (2)
C5—H5B	0.9600	C18—C19	1.392 (2)
C5—H5C	0.9600	C18—C24	1.495 (2)
C1'—C5'	1.465 (7)	C19—C20	1.393 (2)
C1'—N1	1.494 (2)	C19—H19	0.9300
C1'—H1'	0.9800	C20—C21	1.386 (2)
C5'—H5'1	0.9600	C20—C25	1.512 (2)
C5'—H5'2	0.9600	C21—C22	1.372 (3)
C5'—H5'3	0.9600	C21—H21	0.9300
C6—C7	1.387 (2)	C22—F3	1.3594 (19)
C6—N2	1.395 (2)	C22—C23	1.374 (3)
C6—C11	1.402 (2)	C23—H23	0.9300
C7—F1	1.354 (2)	C24—O4	1.200 (2)
C7—C8	1.407 (2)	C24—O5	1.308 (2)
C8—C9	1.402 (3)	C25—O7	1.249 (2)
C8—N3	1.405 (2)	C25—O6	1.252 (2)
C9—C10	1.395 (3)	N1—H1A	0.8900
C9—C12	1.460 (2)	N1—H1B	0.8900
C10—C11	1.355 (2)	O2—H2	0.8200
C10—H10	0.9300	O5—H5	0.8200
C11—F2	1.351 (2)
N2—C2—C1	110.44 (14)	O1—C12—C9	121.66 (19)
N2—C2—C1'	110.44 (14)	C13—C12—C9	115.34 (19)
N2—C2—H2A	109.6	C14—C13—C12	120.31 (17)
C1—C2—H2A	109.6	C14—C13—C15	118.4 (2)
N2—C2—H2B	109.6	C12—C13—C15	121.3 (2)
C1—C2—H2B	109.6	N3—C14—C13	125.18 (19)
H2A—C2—H2B	108.1	N3—C14—H14	117.4
N2—C3—C4	110.04 (14)	C13—C14—H14	117.4
N2—C3—H3A	109.7	O3—C15—O2	122.4 (2)
C4—C3—H3A	109.7	O3—C15—C13	122.0 (3)
N2—C3—H3B	109.7	O2—C15—C13	115.6 (2)
C4—C3—H3B	109.7	N3—C16—C17	112.61 (17)
H3A—C3—H3B	108.2	N3—C16—H16A	109.1
N1—C4—C3	110.75 (14)	C17—C16—H16A	109.1
N1—C4—H4A	109.5	N3—C16—H16B	109.1
C3—C4—H4A	109.5	C17—C16—H16B	109.1
N1—C4—H4B	109.5	H16A—C16—H16B	107.8
C3—C4—H4B	109.5	C16—C17—H17A	109.5
H4A—C4—H4B	108.1	C16—C17—H17B	109.5
N1—C1—C5	111.26 (18)	H17A—C17—H17B	109.5
N1—C1—C2	107.76 (14)	C16—C17—H17C	109.5
C5—C1—C2	111.7 (2)	H17A—C17—H17C	109.5
N1—C1—H1	108.7	H17B—C17—H17C	109.5
C5—C1—H1	108.7	C23—C18—C19	120.05 (15)
C2—C1—H1	108.7	C23—C18—C24	117.27 (15)
C1—C5—H5A	109.5	C19—C18—C24	122.67 (15)
C1—C5—H5B	109.5	C18—C19—C20	120.20 (15)
H5A—C5—H5B	109.5	C18—C19—H19	119.9
C1—C5—H5C	109.5	C20—C19—H19	119.9
H5A—C5—H5C	109.5	C21—C20—C19	119.84 (16)
H5B—C5—H5C	109.5	C21—C20—C25	119.31 (15)
C5'—C1'—N1	114.0 (3)	C19—C20—C25	120.85 (14)
C5'—C1'—C2	113.4 (3)	C22—C21—C20	118.46 (16)
N1—C1'—C2	107.76 (14)	C22—C21—H21	120.8
C5'—C1'—H1'	107.1	C20—C21—H21	120.8
N1—C1'—H1'	107.1	F3—C22—C21	118.36 (16)
C2—C1'—H1'	107.1	F3—C22—C23	118.42 (16)
C1'—C5'—H5'1	109.5	C21—C22—C23	123.22 (15)
C1'—C5'—H5'2	109.5	C22—C23—C18	118.23 (16)
H5'1—C5'—H5'2	109.5	C22—C23—H23	120.9
C1'—C5'—H5'3	109.5	C18—C23—H23	120.9
H5'1—C5'—H5'3	109.5	O4—C24—O5	123.81 (17)
H5'2—C5'—H5'3	109.5	O4—C24—C18	121.90 (17)
C7—C6—N2	125.94 (15)	O5—C24—C18	114.29 (15)
C7—C6—C11	114.87 (14)	O7—C25—O6	123.89 (17)
N2—C6—C11	119.18 (14)	O7—C25—C20	118.06 (15)
F1—C7—C6	116.89 (14)	O6—C25—C20	118.06 (15)
F1—C7—C8	118.88 (15)	C4—N1—C1'	111.92 (13)
C6—C7—C8	124.17 (16)	C4—N1—C1	111.92 (13)
C9—C8—N3	119.17 (15)	C4—N1—H1A	109.2
C9—C8—C7	117.20 (15)	C1—N1—H1A	109.2
N3—C8—C7	123.56 (17)	C4—N1—H1B	109.2
C10—C9—C8	119.86 (15)	C1—N1—H1B	109.2
C10—C9—C12	118.66 (18)	H1A—N1—H1B	107.9
C8—C9—C12	121.49 (17)	C6—N2—C3	121.34 (13)
C11—C10—C9	119.92 (17)	C6—N2—C2	116.36 (13)
C11—C10—H10	120.0	C3—N2—C2	111.61 (13)
C9—C10—H10	120.0	C14—N3—C8	118.45 (18)
F2—C11—C10	118.87 (16)	C14—N3—C16	117.24 (17)
F2—C11—C6	117.42 (14)	C8—N3—C16	124.05 (16)
C10—C11—C6	123.71 (16)	C15—O2—H2	109.5
O1—C12—C13	123.00 (18)	C24—O5—H5	109.5
N2—C3—C4—N1	54.3 (2)	C18—C19—C20—C25	−179.48 (16)
N2—C2—C1—N1	−59.2 (2)	C19—C20—C21—C22	−1.1 (3)
N2—C2—C1—C5	178.3 (2)	C25—C20—C21—C22	179.11 (16)
N2—C2—C1'—C5'	67.9 (4)	C20—C21—C22—F3	179.86 (15)
N2—C2—C1'—N1	−59.2 (2)	C20—C21—C22—C23	0.8 (3)
N2—C6—C7—F1	3.7 (3)	F3—C22—C23—C18	−179.23 (16)
C11—C6—C7—F1	−175.55 (15)	C21—C22—C23—C18	−0.2 (3)
N2—C6—C7—C8	−179.07 (16)	C19—C18—C23—C22	−0.2 (3)
C11—C6—C7—C8	1.7 (3)	C24—C18—C23—C22	−179.07 (16)
F1—C7—C8—C9	171.85 (15)	C23—C18—C24—O4	12.6 (3)
C6—C7—C8—C9	−5.3 (3)	C19—C18—C24—O4	−166.2 (2)
F1—C7—C8—N3	−5.2 (3)	C23—C18—C24—O5	−168.50 (16)
C6—C7—C8—N3	177.68 (16)	C19—C18—C24—O5	12.6 (3)
N3—C8—C9—C10	−178.45 (15)	C21—C20—C25—O7	12.1 (3)
C7—C8—C9—C10	4.4 (2)	C19—C20—C25—O7	−167.74 (18)
N3—C8—C9—C12	1.7 (2)	C21—C20—C25—O6	−167.64 (17)
C7—C8—C9—C12	−175.47 (15)	C19—C20—C25—O6	12.5 (3)
C8—C9—C10—C11	−0.1 (3)	C3—C4—N1—C1'	−55.9 (2)
C12—C9—C10—C11	179.77 (16)	C3—C4—N1—C1	−55.9 (2)
C9—C10—C11—F2	175.67 (15)	C5'—C1'—N1—C4	−69.3 (3)
C9—C10—C11—C6	−3.9 (3)	C2—C1'—N1—C4	57.47 (19)
C7—C6—C11—F2	−176.49 (15)	C5—C1—N1—C4	−179.7 (2)
N2—C6—C11—F2	4.2 (2)	C2—C1—N1—C4	57.47 (19)
C7—C6—C11—C10	3.1 (3)	C7—C6—N2—C3	22.2 (3)
N2—C6—C11—C10	−176.24 (16)	C11—C6—N2—C3	−158.57 (16)
C10—C9—C12—O1	0.1 (3)	C7—C6—N2—C2	−119.34 (19)
C8—C9—C12—O1	179.95 (17)	C11—C6—N2—C2	59.9 (2)
C10—C9—C12—C13	−179.44 (16)	C4—C3—N2—C6	159.44 (15)
C8—C9—C12—C13	0.4 (2)	C4—C3—N2—C2	−57.40 (19)
O1—C12—C13—C14	178.65 (19)	C1—C2—N2—C6	−153.88 (15)
C9—C12—C13—C14	−1.8 (3)	C1'—C2—N2—C6	−153.88 (15)
O1—C12—C13—C15	−1.3 (3)	C1—C2—N2—C3	61.0 (2)
C9—C12—C13—C15	178.26 (17)	C1'—C2—N2—C3	61.0 (2)
C12—C13—C14—N3	1.2 (3)	C13—C14—N3—C8	1.0 (3)
C15—C13—C14—N3	−178.91 (19)	C13—C14—N3—C16	−173.3 (2)
C14—C13—C15—O3	−3.4 (3)	C9—C8—N3—C14	−2.4 (2)
C12—C13—C15—O3	176.5 (2)	C7—C8—N3—C14	174.54 (17)
C14—C13—C15—O2	176.5 (2)	C9—C8—N3—C16	171.48 (18)
C12—C13—C15—O2	−3.6 (3)	C7—C8—N3—C16	−11.6 (3)
C23—C18—C19—C20	−0.1 (3)	C17—C16—N3—C14	104.7 (2)
C24—C18—C19—C20	178.77 (16)	C17—C16—N3—C8	−69.3 (2)
C18—C19—C20—C21	0.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O7^i	0.82	1.75	2.557 (2)	167
O2—H2···O1	0.82	1.78	2.535 (3)	153
N1—H1B···O7^ii	0.89	2.48	3.046 (2)	122
N1—H1B···O6^ii	0.89	1.91	2.790 (2)	170
N1—H1A···O3^iii	0.89	1.94	2.811 (2)	165
C21—H21···O4^iv	0.93	2.61	3.534 (3)	173
C17—H17C···F1	0.96	2.45	2.985 (3)	115
C17—H17B···F3^v	0.96	2.53	3.380 (3)	148
C16—H16B···F1^v	0.97	2.48	3.394 (3)	157
C16—H16B···F1	0.97	2.16	2.682 (2)	112
C16—H16A···O6^vi	0.97	2.35	3.287 (3)	162
C14—H14···O6^vi	0.93	2.59	3.448 (3)	154
C4—H4A···O4^v	0.97	2.60	3.274 (3)	127
C2—H2B···F2	0.97	2.30	2.883 (2)	118
C2—H2A···F3	0.97	2.57	3.078 (2)	113

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x−1/2, −y+1/2, z+1/2; (iii) x, y, z+1; (iv) x+1/2, −y+1/2, z+1/2; (v) −x, −y, −z+1; (vi) −x+1/2, y−1/2, −z+1/2.