The title compound hydroxyethylammonium enrofloxacinate [systematic name: 2-hydroxyethanaminium 1-cyclopropyl-7-(4-ethylpiperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate], C2H8NO+·C19H21FN3O3-, contains enrofloxacinate anions and 2-hydroxyethanaminium cations. The quinoline ring system in the anions is essentially planar. The piperazine moiety adopts a chair conformation. The cations lie parallel to each other about inversion centers. The structure is stabilized by strong intermolecular hydrogen bonds involving the carbonyl, carboxyl and terminal piperazine N groups of the anion and the hydroxyl and ammonium groups of the cation.
Supporting information
CCDC reference: 252970
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.002 Å
- R factor = 0.037
- wR factor = 0.102
- Data-to-parameter ratio = 12.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.05
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
C2 H8 N O
Alert level G
FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and _chemical_formula_moiety. This is
usually due to the moiety formula being in the wrong format.
Atom count from _chemical_formula_sum: C21 H29 F1 N4 O4
Atom count from _chemical_formula_moiety:C21 H28 F1 N4 O4
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Siemens, 1991); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
2-hydroxyethanaminium
1-cyclopropyl-7-(4-ethylpiperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-
3-carboxylate
top
Crystal data top
C2H8NO+·C19H21FN3O3− | Z = 2 |
Mr = 420.48 | F(000) = 448 |
Triclinic, P1 | Dx = 1.307 Mg m−3 |
a = 9.791 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.858 (1) Å | Cell parameters from 34 reflections |
c = 12.274 (2) Å | θ = 4.3–15.9° |
α = 69.12 (1)° | µ = 0.10 mm−1 |
β = 75.74 (1)° | T = 298 K |
γ = 89.54 (1)° | Prism, colourless |
V = 1068.5 (3) Å3 | 0.54 × 0.32 × 0.24 mm |
Data collection top
Siemens P4 diffractometer | Rint = 0.009 |
Radiation source: normal-focus sealed tube | θmax = 25.5°, θmin = 1.8° |
Graphite monochromator | h = 0→11 |
ω scans | k = −11→11 |
4509 measured reflections | l = −14→14 |
3932 independent reflections | 3 standard reflections every 97 reflections |
2733 reflections with I > 2σ(I) | intensity decay: 5.3% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.037 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.102 | w = 1/[σ2(Fo2) + (0.06P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.95 | (Δ/σ)max < 0.001 |
3932 reflections | Δρmax = 0.20 e Å−3 |
309 parameters | Δρmin = −0.15 e Å−3 |
3 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.041 (3) |
Special details top
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) top | x | y | z | Uiso*/Ueq | |
F | 0.12637 (9) | 0.86744 (12) | 0.54017 (9) | 0.0505 (3) | |
O1 | 0.36721 (12) | 0.67145 (14) | 0.23093 (11) | 0.0471 (3) | |
O2 | 0.56004 (12) | 0.51011 (15) | 0.12676 (11) | 0.0501 (4) | |
O3 | 0.77943 (13) | 0.55956 (15) | 0.12782 (11) | 0.0523 (4) | |
N1 | 0.64753 (12) | 0.66343 (14) | 0.43101 (10) | 0.0294 (3) | |
N2 | 0.30620 (13) | 0.86371 (14) | 0.68422 (11) | 0.0334 (3) | |
N3 | 0.24206 (13) | 0.89893 (14) | 0.91446 (11) | 0.0333 (3) | |
C1 | 0.67977 (16) | 0.61612 (17) | 0.33756 (13) | 0.0310 (4) | |
H1 | 0.7683 | 0.5818 | 0.3207 | 0.037* | |
C2 | 0.59316 (16) | 0.61457 (16) | 0.26589 (13) | 0.0295 (3) | |
C3 | 0.45509 (16) | 0.66592 (17) | 0.28962 (13) | 0.0306 (4) | |
C4 | 0.41992 (15) | 0.71469 (16) | 0.39266 (13) | 0.0289 (3) | |
C5 | 0.28787 (16) | 0.76665 (18) | 0.42289 (14) | 0.0343 (4) | |
H5 | 0.2233 | 0.7702 | 0.3778 | 0.041* | |
C6 | 0.25381 (16) | 0.81187 (18) | 0.51763 (14) | 0.0343 (4) | |
C7 | 0.34529 (16) | 0.80887 (17) | 0.59066 (13) | 0.0312 (4) | |
C8 | 0.47568 (16) | 0.75818 (17) | 0.56029 (13) | 0.0313 (4) | |
H8 | 0.5392 | 0.7540 | 0.6064 | 0.038* | |
C9 | 0.51481 (15) | 0.71278 (16) | 0.46154 (13) | 0.0276 (3) | |
C10 | 0.74810 (17) | 0.65515 (19) | 0.50256 (15) | 0.0347 (4) | |
C11 | 0.81819 (19) | 0.7930 (2) | 0.49433 (19) | 0.0456 (5) | |
C12 | 0.90070 (19) | 0.6947 (2) | 0.44053 (19) | 0.0475 (5) | |
C13 | 0.64817 (18) | 0.55797 (18) | 0.16547 (14) | 0.0360 (4) | |
C14 | 0.17424 (16) | 0.79522 (19) | 0.77874 (14) | 0.0370 (4) | |
H14A | 0.1886 | 0.6970 | 0.8274 | 0.044* | |
H14B | 0.0994 | 0.7891 | 0.7411 | 0.044* | |
C15 | 0.13091 (16) | 0.88291 (18) | 0.85853 (14) | 0.0368 (4) | |
H15A | 0.1096 | 0.9786 | 0.8107 | 0.044* | |
H15B | 0.0457 | 0.8350 | 0.9211 | 0.044* | |
C16 | 0.36874 (17) | 0.97171 (19) | 0.81746 (14) | 0.0370 (4) | |
H16A | 0.4437 | 0.9855 | 0.8525 | 0.044* | |
H16B | 0.3480 | 1.0670 | 0.7684 | 0.044* | |
C17 | 0.41834 (16) | 0.88398 (19) | 0.73853 (14) | 0.0359 (4) | |
H17A | 0.5023 | 0.9344 | 0.6754 | 0.043* | |
H17B | 0.4425 | 0.7898 | 0.7866 | 0.043* | |
C18 | 0.19244 (19) | 0.9873 (2) | 0.98965 (16) | 0.0439 (4) | |
H18A | 0.1055 | 0.9387 | 1.0495 | 0.053* | |
H18B | 0.1706 | 1.0809 | 0.9386 | 0.053* | |
C19 | 0.2967 (2) | 1.0131 (3) | 1.05369 (19) | 0.0627 (6) | |
H19A | 0.3303 | 0.9221 | 1.0948 | 0.075* | |
H19B | 0.2513 | 1.0552 | 1.1113 | 0.075* | |
H19C | 0.3751 | 1.0785 | 0.9958 | 0.075* | |
O4 | 1.01557 (14) | 0.65443 (15) | 0.15994 (12) | 0.0562 (4) | |
N4 | 1.29740 (15) | 0.58467 (17) | 0.05639 (12) | 0.0371 (4) | |
C20 | 1.07615 (19) | 0.5288 (2) | 0.22023 (16) | 0.0490 (5) | |
H20A | 1.0015 | 0.4524 | 0.2712 | 0.059* | |
H20B | 1.1263 | 0.5506 | 0.2718 | 0.059* | |
C21 | 1.17689 (19) | 0.4754 (2) | 0.13325 (16) | 0.0498 (5) | |
H21A | 1.2126 | 0.3865 | 0.1783 | 0.060* | |
H21B | 1.1264 | 0.4527 | 0.0822 | 0.060* | |
H4O | 0.930 (3) | 0.624 (3) | 0.144 (2) | 0.112 (9)* | |
H10 | 0.7227 (17) | 0.5763 (18) | 0.5803 (16) | 0.045 (5)* | |
H11A | 0.8312 (18) | 0.7950 (18) | 0.5708 (16) | 0.050 (5)* | |
H11B | 0.7895 (18) | 0.882 (2) | 0.4427 (16) | 0.052 (5)* | |
H12A | 0.9271 (19) | 0.7278 (19) | 0.3526 (18) | 0.055 (5)* | |
H12B | 0.968 (2) | 0.636 (2) | 0.4803 (17) | 0.061 (6)* | |
H4A | 1.268 (2) | 0.6747 (13) | 0.0226 (17) | 0.068 (7)* | |
H4B | 1.3444 (17) | 0.5546 (18) | −0.0032 (12) | 0.050 (5)* | |
H4C | 1.3569 (16) | 0.5968 (19) | 0.0984 (14) | 0.051 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F | 0.0336 (5) | 0.0815 (8) | 0.0585 (6) | 0.0223 (5) | −0.0184 (5) | −0.0477 (6) |
O1 | 0.0402 (7) | 0.0768 (9) | 0.0494 (7) | 0.0181 (6) | −0.0237 (6) | −0.0448 (7) |
O2 | 0.0446 (7) | 0.0761 (9) | 0.0569 (8) | 0.0168 (6) | −0.0220 (6) | −0.0508 (7) |
O3 | 0.0383 (7) | 0.0853 (10) | 0.0550 (8) | 0.0190 (7) | −0.0150 (6) | −0.0495 (8) |
N1 | 0.0276 (7) | 0.0395 (8) | 0.0276 (7) | 0.0054 (6) | −0.0102 (5) | −0.0180 (6) |
N2 | 0.0267 (7) | 0.0472 (8) | 0.0317 (7) | 0.0002 (6) | −0.0031 (6) | −0.0237 (6) |
N3 | 0.0322 (7) | 0.0435 (8) | 0.0290 (7) | 0.0055 (6) | −0.0032 (6) | −0.0223 (6) |
C1 | 0.0305 (8) | 0.0361 (9) | 0.0313 (8) | 0.0071 (7) | −0.0075 (7) | −0.0185 (7) |
C2 | 0.0326 (8) | 0.0322 (9) | 0.0288 (8) | 0.0044 (7) | −0.0085 (7) | −0.0168 (7) |
C3 | 0.0338 (9) | 0.0346 (9) | 0.0282 (8) | 0.0007 (7) | −0.0095 (7) | −0.0160 (7) |
C4 | 0.0275 (8) | 0.0339 (9) | 0.0275 (8) | −0.0004 (7) | −0.0063 (6) | −0.0143 (7) |
C5 | 0.0267 (8) | 0.0483 (10) | 0.0360 (9) | 0.0028 (7) | −0.0111 (7) | −0.0229 (8) |
C6 | 0.0262 (8) | 0.0449 (10) | 0.0373 (9) | 0.0055 (7) | −0.0064 (7) | −0.0227 (8) |
C7 | 0.0295 (8) | 0.0370 (9) | 0.0299 (8) | −0.0011 (7) | −0.0041 (7) | −0.0180 (7) |
C8 | 0.0308 (8) | 0.0404 (9) | 0.0282 (8) | 0.0017 (7) | −0.0093 (7) | −0.0179 (7) |
C9 | 0.0258 (8) | 0.0323 (8) | 0.0257 (8) | 0.0005 (6) | −0.0050 (6) | −0.0130 (7) |
C10 | 0.0318 (9) | 0.0463 (10) | 0.0318 (9) | 0.0061 (8) | −0.0140 (7) | −0.0171 (8) |
C11 | 0.0428 (11) | 0.0546 (13) | 0.0508 (11) | 0.0023 (9) | −0.0192 (9) | −0.0278 (10) |
C12 | 0.0321 (10) | 0.0716 (14) | 0.0507 (12) | 0.0094 (9) | −0.0148 (9) | −0.0339 (11) |
C13 | 0.0398 (10) | 0.0433 (10) | 0.0353 (9) | 0.0134 (8) | −0.0150 (8) | −0.0232 (8) |
C14 | 0.0289 (8) | 0.0497 (10) | 0.0360 (9) | −0.0007 (7) | −0.0038 (7) | −0.0232 (8) |
C15 | 0.0303 (9) | 0.0484 (10) | 0.0337 (9) | 0.0055 (8) | −0.0041 (7) | −0.0203 (8) |
C16 | 0.0349 (9) | 0.0461 (10) | 0.0350 (9) | −0.0002 (8) | −0.0055 (7) | −0.0231 (8) |
C17 | 0.0292 (8) | 0.0500 (10) | 0.0318 (8) | −0.0014 (7) | −0.0029 (7) | −0.0221 (8) |
C18 | 0.0461 (10) | 0.0533 (11) | 0.0406 (10) | 0.0121 (9) | −0.0070 (8) | −0.0298 (9) |
C19 | 0.0708 (14) | 0.0846 (16) | 0.0564 (12) | 0.0200 (12) | −0.0211 (11) | −0.0510 (12) |
O4 | 0.0400 (8) | 0.0660 (9) | 0.0591 (8) | 0.0031 (7) | −0.0062 (7) | −0.0232 (7) |
N4 | 0.0339 (8) | 0.0562 (10) | 0.0329 (8) | 0.0113 (7) | −0.0123 (6) | −0.0278 (8) |
C20 | 0.0404 (10) | 0.0697 (13) | 0.0383 (10) | −0.0010 (9) | −0.0073 (8) | −0.0233 (10) |
C21 | 0.0482 (11) | 0.0584 (12) | 0.0473 (11) | 0.0012 (9) | −0.0088 (9) | −0.0270 (10) |
Geometric parameters (Å, º) top
F—C6 | 1.3639 (17) | C11—H11B | 0.971 (18) |
O1—C3 | 1.2405 (18) | C12—H12A | 0.975 (19) |
O2—C13 | 1.2495 (18) | C12—H12B | 0.98 (2) |
O3—C13 | 1.2522 (19) | C14—C15 | 1.510 (2) |
N1—C1 | 1.3539 (18) | C14—H14A | 0.9700 |
N1—C9 | 1.3948 (18) | C14—H14B | 0.9700 |
N1—C10 | 1.4564 (18) | C15—H15A | 0.9700 |
N2—C7 | 1.4071 (18) | C15—H15B | 0.9700 |
N2—C17 | 1.4659 (19) | C16—C17 | 1.510 (2) |
N2—C14 | 1.4792 (19) | C16—H16A | 0.9700 |
N3—C15 | 1.4589 (19) | C16—H16B | 0.9700 |
N3—C16 | 1.466 (2) | C17—H17A | 0.9700 |
N3—C18 | 1.4805 (18) | C17—H17B | 0.9700 |
C1—C2 | 1.368 (2) | C18—C19 | 1.506 (2) |
C1—H1 | 0.9300 | C18—H18A | 0.9700 |
C2—C3 | 1.438 (2) | C18—H18B | 0.9700 |
C2—C13 | 1.510 (2) | C19—H19A | 0.9600 |
C3—C4 | 1.471 (2) | C19—H19B | 0.9600 |
C4—C9 | 1.398 (2) | C19—H19C | 0.9600 |
C4—C5 | 1.400 (2) | O4—C20 | 1.408 (2) |
C5—C6 | 1.356 (2) | O4—H4O | 0.98 (3) |
C5—H5 | 0.9300 | N4—C21 | 1.480 (2) |
C6—C7 | 1.408 (2) | N4—H4A | 0.915 (9) |
C7—C8 | 1.381 (2) | N4—H4B | 0.906 (9) |
C8—C9 | 1.404 (2) | N4—H4C | 0.901 (9) |
C8—H8 | 0.9300 | C20—C21 | 1.505 (2) |
C10—C12 | 1.484 (2) | C20—H20A | 0.9700 |
C10—C11 | 1.486 (2) | C20—H20B | 0.9700 |
C10—H10 | 0.966 (17) | C21—H21A | 0.9700 |
C11—C12 | 1.486 (3) | C21—H21B | 0.9700 |
C11—H11A | 0.985 (18) | | |
| | | |
C1—N1—C9 | 119.35 (12) | O3—C13—C2 | 117.77 (14) |
C1—N1—C10 | 119.96 (12) | N2—C14—C15 | 110.52 (13) |
C9—N1—C10 | 120.60 (12) | N2—C14—H14A | 109.5 |
C7—N2—C17 | 116.34 (12) | C15—C14—H14A | 109.5 |
C7—N2—C14 | 116.55 (12) | N2—C14—H14B | 109.5 |
C17—N2—C14 | 110.64 (12) | C15—C14—H14B | 109.5 |
C15—N3—C16 | 107.78 (12) | H14A—C14—H14B | 108.1 |
C15—N3—C18 | 108.34 (12) | N3—C15—C14 | 111.62 (13) |
C16—N3—C18 | 111.05 (13) | N3—C15—H15A | 109.3 |
N1—C1—C2 | 125.49 (14) | C14—C15—H15A | 109.3 |
N1—C1—H1 | 117.3 | N3—C15—H15B | 109.3 |
C2—C1—H1 | 117.3 | C14—C15—H15B | 109.3 |
C1—C2—C3 | 118.91 (13) | H15A—C15—H15B | 108.0 |
C1—C2—C13 | 117.77 (14) | N3—C16—C17 | 111.47 (13) |
C3—C2—C13 | 123.32 (13) | N3—C16—H16A | 109.3 |
O1—C3—C2 | 125.29 (13) | C17—C16—H16A | 109.3 |
O1—C3—C4 | 119.46 (14) | N3—C16—H16B | 109.3 |
C2—C3—C4 | 115.25 (13) | C17—C16—H16B | 109.3 |
C9—C4—C5 | 118.24 (13) | H16A—C16—H16B | 108.0 |
C9—C4—C3 | 122.26 (13) | N2—C17—C16 | 109.77 (13) |
C5—C4—C3 | 119.50 (13) | N2—C17—H17A | 109.7 |
C6—C5—C4 | 120.22 (14) | C16—C17—H17A | 109.7 |
C6—C5—H5 | 119.9 | N2—C17—H17B | 109.7 |
C4—C5—H5 | 119.9 | C16—C17—H17B | 109.7 |
C5—C6—F | 117.96 (14) | H17A—C17—H17B | 108.2 |
C5—C6—C7 | 123.24 (14) | N3—C18—C19 | 114.46 (14) |
F—C6—C7 | 118.76 (13) | N3—C18—H18A | 108.6 |
C8—C7—N2 | 123.06 (14) | C19—C18—H18A | 108.6 |
C8—C7—C6 | 116.39 (13) | N3—C18—H18B | 108.6 |
N2—C7—C6 | 120.44 (14) | C19—C18—H18B | 108.6 |
C7—C8—C9 | 121.66 (14) | H18A—C18—H18B | 107.6 |
C7—C8—H8 | 119.2 | C18—C19—H19A | 109.5 |
C9—C8—H8 | 119.2 | C18—C19—H19B | 109.5 |
N1—C9—C4 | 118.71 (12) | H19A—C19—H19B | 109.5 |
N1—C9—C8 | 121.06 (13) | C18—C19—H19C | 109.5 |
C4—C9—C8 | 120.23 (14) | H19A—C19—H19C | 109.5 |
N1—C10—C12 | 119.24 (14) | H19B—C19—H19C | 109.5 |
N1—C10—C11 | 118.67 (15) | C20—O4—H4O | 108.6 (16) |
C12—C10—C11 | 60.02 (12) | C21—N4—H4A | 111.7 (13) |
N1—C10—H10 | 113.3 (10) | C21—N4—H4B | 108.0 (11) |
C12—C10—H10 | 117.9 (10) | H4A—N4—H4B | 109.1 (17) |
C11—C10—H10 | 117.9 (10) | C21—N4—H4C | 112.4 (11) |
C12—C11—C10 | 59.90 (12) | H4A—N4—H4C | 105.7 (16) |
C12—C11—H11A | 118.6 (10) | H4B—N4—H4C | 109.9 (16) |
C10—C11—H11A | 115.5 (10) | O4—C20—C21 | 111.92 (15) |
C12—C11—H11B | 120.1 (11) | O4—C20—H20A | 109.2 |
C10—C11—H11B | 116.0 (10) | C21—C20—H20A | 109.2 |
H11A—C11—H11B | 115.1 (15) | O4—C20—H20B | 109.2 |
C10—C12—C11 | 60.08 (12) | C21—C20—H20B | 109.2 |
C10—C12—H12A | 116.9 (11) | H20A—C20—H20B | 107.9 |
C11—C12—H12A | 116.4 (11) | N4—C21—C20 | 112.03 (15) |
C10—C12—H12B | 117.1 (11) | N4—C21—H21A | 109.2 |
C11—C12—H12B | 119.7 (11) | C20—C21—H21A | 109.2 |
H12A—C12—H12B | 115.4 (16) | N4—C21—H21B | 109.2 |
O2—C13—O3 | 124.18 (14) | C20—C21—H21B | 109.2 |
O2—C13—C2 | 118.03 (14) | H21A—C21—H21B | 107.9 |
| | | |
C9—N1—C1—C2 | 1.5 (2) | C5—C4—C9—N1 | −178.98 (14) |
C10—N1—C1—C2 | 178.18 (15) | C3—C4—C9—N1 | 0.3 (2) |
N1—C1—C2—C3 | −0.4 (2) | C5—C4—C9—C8 | 1.8 (2) |
N1—C1—C2—C13 | 179.81 (14) | C3—C4—C9—C8 | −178.97 (14) |
C1—C2—C3—O1 | 179.32 (15) | C7—C8—C9—N1 | 179.24 (14) |
C13—C2—C3—O1 | −0.9 (3) | C7—C8—C9—C4 | −1.6 (2) |
C1—C2—C3—C4 | −0.7 (2) | C1—N1—C10—C12 | 41.7 (2) |
C13—C2—C3—C4 | 179.10 (14) | C9—N1—C10—C12 | −141.65 (16) |
O1—C3—C4—C9 | −179.27 (15) | C1—N1—C10—C11 | 111.40 (17) |
C2—C3—C4—C9 | 0.7 (2) | C9—N1—C10—C11 | −71.92 (19) |
O1—C3—C4—C5 | 0.0 (2) | N1—C10—C11—C12 | −109.11 (17) |
C2—C3—C4—C5 | 179.98 (14) | N1—C10—C12—C11 | 108.16 (18) |
C9—C4—C5—C6 | −0.8 (2) | C1—C2—C13—O2 | 156.37 (15) |
C3—C4—C5—C6 | 179.94 (15) | C3—C2—C13—O2 | −23.4 (2) |
C4—C5—C6—F | 177.21 (14) | C1—C2—C13—O3 | −22.3 (2) |
C4—C5—C6—C7 | −0.5 (3) | C3—C2—C13—O3 | 157.88 (16) |
C17—N2—C7—C8 | 8.3 (2) | C7—N2—C14—C15 | −169.01 (14) |
C14—N2—C7—C8 | −125.15 (17) | C17—N2—C14—C15 | 55.08 (17) |
C17—N2—C7—C6 | −167.74 (14) | C16—N3—C15—C14 | 59.05 (17) |
C14—N2—C7—C6 | 58.9 (2) | C18—N3—C15—C14 | 179.30 (13) |
C5—C6—C7—C8 | 0.8 (2) | N2—C14—C15—N3 | −57.49 (18) |
F—C6—C7—C8 | −176.93 (14) | C15—N3—C16—C17 | −60.22 (17) |
C5—C6—C7—N2 | 177.03 (15) | C18—N3—C16—C17 | −178.74 (13) |
F—C6—C7—N2 | −0.7 (2) | C7—N2—C17—C16 | 168.14 (13) |
N2—C7—C8—C9 | −175.88 (14) | C14—N2—C17—C16 | −55.84 (17) |
C6—C7—C8—C9 | 0.3 (2) | N3—C16—C17—N2 | 59.56 (18) |
C1—N1—C9—C4 | −1.3 (2) | C15—N3—C18—C19 | 179.95 (16) |
C10—N1—C9—C4 | −178.03 (14) | C16—N3—C18—C19 | −61.9 (2) |
C1—N1—C9—C8 | 177.88 (14) | O4—C20—C21—N4 | 61.6 (2) |
C10—N1—C9—C8 | 1.2 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4O···O3 | 0.98 (3) | 1.69 (3) | 2.6687 (19) | 175 (2) |
N4—H4C···O1i | 0.90 (1) | 2.03 (1) | 2.7973 (17) | 142 (2) |
N4—H4C···O2i | 0.90 (1) | 2.22 (1) | 2.9171 (19) | 134 (1) |
N4—H4B···O2ii | 0.91 (1) | 1.89 (1) | 2.7937 (18) | 179 (2) |
N4—H4A···N3iii | 0.92 (1) | 2.19 (1) | 3.085 (2) | 168 (2) |
Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y+1, −z; (iii) x+1, y, z−1. |