A methanol hemisolvate of ciprofloxacin

The title compound [systematic name: 1-cyclo­propyl-6-fluoro-4-oxo-7-(piperazin-4-ium-1-yl)-1,4-dihydro­quinoline-3-carboxyl­ate methanol hemisolvate], C₁₇H₁₈FN₃O₃·0.5CH₄O, is an anti­bacterial fluoro­quinolone. The mol­ecule exists as a zwitterion in the solid state. The methanol mol­ecule is disordered across a twofold rotation axis.

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in solvent or counterion
• R factor = 0.050
• wR factor = 0.132
• Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C H4 O

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEPII (Johnson 1976) and MS Modeling (Accelrys, 2004); software used to prepare material for publication: SHELXTL.

1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-4-ium-1-yl)-1,4-dihydroquinoline-3- carboxylate methanol hemisolvate

Crystal data

C17H18FN3O3·0.5CH4O	F(000) = 1464
Mr = 347.37	Dx = 1.389 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 26.036 (11) Å	Cell parameters from 918 reflections
b = 12.697 (5) Å	θ = 2.8–28.0°
c = 10.235 (4) Å	µ = 0.11 mm^−1
β = 100.941 (7)°	T = 193 K
V = 3322 (2) Å^3	Needle, colourless
Z = 8	0.4 × 0.1 × 0.1 mm

Data collection

Bruker APEX CCD diffractometer	3174 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.054
Graphite monochromator	θmax = 28.4°, θmin = 1.6°
ω scans	h = −34→34
19542 measured reflections	k = −16→16
4067 independent reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.132	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0834P)^2] where P = (Fo^2 + 2Fc^2)/3
4067 reflections	(Δ/σ)max = 0.004
236 parameters	Δρmax = 0.42 e Å^−3
1 restraint	Δρmin = −0.27 e Å^−3

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
F1	0.31322 (3)	0.30371 (7)	0.17111 (9)	0.0353 (2)
O1	−0.01072 (4)	0.22152 (9)	0.06628 (13)	0.0445 (3)
O2	0.02182 (4)	0.38496 (7)	0.08540 (11)	0.0319 (3)
O3	0.12327 (4)	0.36614 (8)	0.01847 (10)	0.0278 (2)
N1	0.13471 (4)	0.12707 (8)	0.29290 (11)	0.0217 (3)
N2	0.32619 (4)	0.15634 (9)	0.36645 (11)	0.0241 (3)
N3	0.42473 (4)	0.06580 (9)	0.48346 (12)	0.0247 (3)
H1A	0.4582	0.0768	0.5235	0.030*
H1B	0.4192	−0.0042	0.4782	0.030*
C1	0.13796 (5)	0.03814 (11)	0.38372 (15)	0.0287 (3)
H1	0.1485	−0.0289	0.3495	0.034*
C2	0.10033 (7)	0.03035 (15)	0.47579 (18)	0.0460 (5)
H2A	0.0880	−0.0392	0.4941	0.055*
H2B	0.0748	0.0862	0.4732	0.055*
C3	0.15640 (7)	0.05633 (15)	0.52964 (16)	0.0435 (4)
H3A	0.1780	0.0024	0.5802	0.052*
H3B	0.1647	0.1280	0.5593	0.052*
C4	0.18026 (5)	0.17178 (10)	0.26491 (13)	0.0204 (3)
C5	0.08739 (5)	0.16224 (10)	0.22787 (14)	0.0228 (3)
H5	0.0577	0.1281	0.2442	0.027*
C6	0.08065 (5)	0.24431 (10)	0.14029 (14)	0.0220 (3)
C7	0.02596 (5)	0.28519 (11)	0.09177 (15)	0.0263 (3)
C8	0.12511 (5)	0.29326 (10)	0.10155 (13)	0.0212 (3)
C9	0.17597 (5)	0.25132 (10)	0.16800 (13)	0.0203 (3)
C10	0.22188 (5)	0.29428 (11)	0.13676 (14)	0.0248 (3)
H10	0.2197	0.3465	0.0722	0.030*
C11	0.26926 (5)	0.25971 (11)	0.20052 (14)	0.0250 (3)
C12	0.27531 (5)	0.18160 (11)	0.30065 (14)	0.0229 (3)
C13	0.33232 (5)	0.10545 (11)	0.49636 (14)	0.0246 (3)
H13A	0.3221	0.0320	0.4857	0.030*
H13B	0.3102	0.1397	0.5500	0.030*
C14	0.38936 (5)	0.11393 (11)	0.56417 (14)	0.0253 (3)
H14A	0.3984	0.1876	0.5794	0.030*
H14B	0.3942	0.0791	0.6500	0.030*
C15	0.41588 (5)	0.11097 (12)	0.34772 (15)	0.0282 (3)
H15A	0.4369	0.0732	0.2943	0.034*
H15B	0.4268	0.1841	0.3523	0.034*
C16	0.35877 (5)	0.10385 (12)	0.28255 (15)	0.0269 (3)
H16A	0.3534	0.1372	0.1958	0.032*
H16B	0.3486	0.0305	0.2702	0.032*
C17	0.23015 (5)	0.13762 (11)	0.33074 (13)	0.0225 (3)
H17	0.2328	0.0851	0.3950	0.027*
O4	−0.01072 (14)	0.0755 (3)	−0.1677 (4)	0.0812 (11)	0.50
H4	−0.0209	0.1114	−0.1110	0.122*	0.50
C18	0.0001 (11)	0.1404 (5)	−0.2681 (13)	0.124 (3)	0.50
H18C	−0.0313	0.1514	−0.3330	0.187*	0.50
H18A	0.0260	0.1078	−0.3099	0.187*	0.50
H18B	0.0129	0.2069	−0.2309	0.187*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0189 (4)	0.0374 (5)	0.0499 (6)	−0.0029 (3)	0.0072 (4)	0.0134 (4)
O1	0.0202 (5)	0.0301 (6)	0.0782 (9)	−0.0054 (4)	−0.0029 (6)	0.0093 (6)
O2	0.0173 (5)	0.0229 (5)	0.0529 (7)	0.0028 (4)	0.0002 (4)	0.0058 (5)
O3	0.0246 (5)	0.0279 (5)	0.0314 (6)	0.0060 (4)	0.0068 (4)	0.0109 (4)
N1	0.0194 (6)	0.0193 (5)	0.0273 (6)	0.0030 (4)	0.0069 (5)	0.0050 (4)
N2	0.0159 (6)	0.0291 (6)	0.0271 (6)	0.0044 (4)	0.0034 (5)	0.0022 (5)
N3	0.0143 (5)	0.0212 (6)	0.0364 (7)	0.0000 (4)	−0.0010 (5)	−0.0036 (5)
C1	0.0272 (7)	0.0225 (7)	0.0385 (8)	0.0061 (5)	0.0111 (6)	0.0115 (6)
C2	0.0408 (10)	0.0454 (10)	0.0590 (11)	0.0136 (8)	0.0275 (8)	0.0279 (9)
C3	0.0515 (11)	0.0463 (10)	0.0342 (9)	0.0086 (8)	0.0118 (8)	0.0176 (8)
C4	0.0190 (6)	0.0198 (6)	0.0229 (7)	0.0024 (5)	0.0048 (5)	0.0003 (5)
C5	0.0172 (6)	0.0213 (7)	0.0309 (7)	0.0008 (5)	0.0068 (5)	0.0005 (5)
C6	0.0178 (6)	0.0198 (6)	0.0272 (7)	0.0015 (5)	0.0015 (5)	−0.0003 (5)
C7	0.0181 (7)	0.0264 (7)	0.0332 (8)	0.0009 (5)	0.0014 (6)	0.0059 (6)
C8	0.0203 (7)	0.0202 (6)	0.0227 (7)	0.0024 (5)	0.0034 (5)	−0.0001 (5)
C9	0.0176 (6)	0.0203 (6)	0.0231 (7)	0.0021 (5)	0.0039 (5)	0.0011 (5)
C10	0.0233 (7)	0.0229 (7)	0.0285 (7)	0.0011 (5)	0.0055 (6)	0.0070 (6)
C11	0.0175 (6)	0.0262 (7)	0.0321 (8)	−0.0018 (5)	0.0064 (5)	0.0030 (6)
C12	0.0182 (6)	0.0244 (7)	0.0252 (7)	0.0033 (5)	0.0018 (5)	−0.0005 (5)
C13	0.0189 (7)	0.0284 (7)	0.0260 (7)	0.0042 (5)	0.0032 (5)	0.0013 (6)
C14	0.0203 (7)	0.0261 (7)	0.0279 (7)	0.0020 (5)	0.0002 (5)	−0.0008 (5)
C15	0.0197 (7)	0.0303 (8)	0.0354 (8)	0.0012 (5)	0.0072 (6)	−0.0016 (6)
C16	0.0197 (7)	0.0330 (8)	0.0281 (7)	0.0036 (5)	0.0045 (5)	−0.0014 (6)
C17	0.0217 (7)	0.0219 (7)	0.0238 (7)	0.0036 (5)	0.0041 (5)	0.0039 (5)
O4	0.096 (3)	0.085 (3)	0.073 (2)	−0.035 (2)	0.042 (2)	−0.019 (2)
C18	0.253 (8)	0.093 (4)	0.034 (7)	−0.049 (9)	0.045 (7)	−0.011 (4)

Geometric parameters (Å, º)

F1—C11	1.3579 (16)	C5—H5	0.9300
O1—C7	1.2405 (17)	C6—C8	1.4345 (18)
O2—C7	1.2720 (17)	C6—C7	1.5085 (19)
O3—C8	1.2514 (16)	C8—C9	1.4689 (18)
N1—C5	1.3597 (17)	C9—C10	1.4049 (19)
N1—C4	1.3926 (17)	C10—C11	1.3545 (19)
N1—C1	1.4548 (17)	C10—H10	0.9300
N2—C12	1.4046 (17)	C11—C12	1.413 (2)
N2—C13	1.4596 (18)	C12—C17	1.3880 (19)
N2—C16	1.4756 (18)	C13—C14	1.5190 (19)
N3—C15	1.4801 (19)	C13—H13A	0.9700
N3—C14	1.4807 (18)	C13—H13B	0.9700
N3—H1A	0.9000	C14—H14A	0.9700
N3—H1B	0.9000	C14—H14B	0.9700
C1—C2	1.486 (2)	C15—C16	1.5124 (19)
C1—C3	1.497 (2)	C15—H15A	0.9700
C1—H1	0.9800	C15—H15B	0.9700
C2—C3	1.496 (3)	C16—H16A	0.9700
C2—H2A	0.9700	C16—H16B	0.9700
C2—H2B	0.9700	C17—H17	0.9300
C3—H3A	0.9700	O4—C18	1.386 (8)
C3—H3B	0.9700	O4—H4	0.8200
C4—C9	1.4051 (19)	C18—H18C	0.9600
C4—C17	1.4133 (18)	C18—H18A	0.9600
C5—C6	1.3640 (19)	C18—H18B	0.9600
C5—N1—C4	119.55 (11)	O3—C8—C9	119.85 (12)
C5—N1—C1	120.33 (11)	C6—C8—C9	114.75 (12)
C4—N1—C1	119.96 (11)	C10—C9—C4	118.86 (12)
C12—N2—C13	117.90 (11)	C10—C9—C8	119.02 (12)
C12—N2—C16	114.72 (11)	C4—C9—C8	122.09 (12)
C13—N2—C16	110.78 (11)	C11—C10—C9	120.06 (13)
C15—N3—C14	111.17 (11)	C11—C10—H10	120.0
C15—N3—H1A	109.4	C9—C10—H10	120.0
C14—N3—H1A	109.4	C10—C11—F1	119.26 (12)
C15—N3—H1B	109.4	C10—C11—C12	122.87 (13)
C14—N3—H1B	109.4	F1—C11—C12	117.83 (12)
H1A—N3—H1B	108.0	C17—C12—N2	124.29 (13)
N1—C1—C2	119.44 (12)	C17—C12—C11	117.43 (12)
N1—C1—C3	119.10 (13)	N2—C12—C11	118.23 (12)
C2—C1—C3	60.20 (12)	N2—C13—C14	108.25 (11)
N1—C1—H1	115.6	N2—C13—H13A	110.0
C2—C1—H1	115.6	C14—C13—H13A	110.0
C3—C1—H1	115.6	N2—C13—H13B	110.0
C1—C2—C3	60.28 (11)	C14—C13—H13B	110.0
C1—C2—H2A	117.7	H13A—C13—H13B	108.4
C3—C2—H2A	117.7	N3—C14—C13	111.93 (11)
C1—C2—H2B	117.7	N3—C14—H14A	109.2
C3—C2—H2B	117.7	C13—C14—H14A	109.2
H2A—C2—H2B	114.9	N3—C14—H14B	109.2
C2—C3—C1	59.52 (11)	C13—C14—H14B	109.2
C2—C3—H3A	117.8	H14A—C14—H14B	107.9
C1—C3—H3A	117.8	N3—C15—C16	110.84 (11)
C2—C3—H3B	117.8	N3—C15—H15A	109.5
C1—C3—H3B	117.8	C16—C15—H15A	109.5
H3A—C3—H3B	115.0	N3—C15—H15B	109.5
N1—C4—C9	118.78 (11)	C16—C15—H15B	109.5
N1—C4—C17	121.22 (12)	H15A—C15—H15B	108.1
C9—C4—C17	119.99 (12)	N2—C16—C15	109.99 (12)
N1—C5—C6	124.35 (12)	N2—C16—H16A	109.7
N1—C5—H5	117.8	C15—C16—H16A	109.7
C6—C5—H5	117.8	N2—C16—H16B	109.7
C5—C6—C8	120.18 (12)	C15—C16—H16B	109.7
C5—C6—C7	118.36 (12)	H16A—C16—H16B	108.2
C8—C6—C7	121.39 (12)	C12—C17—C4	120.76 (12)
O1—C7—O2	125.74 (13)	C12—C17—H17	119.6
O1—C7—C6	119.07 (13)	C4—C17—H17	119.6
O2—C7—C6	115.15 (12)	C18—O4—H4	109.5
O3—C8—C6	125.40 (12)
C5—N1—C1—C2	−41.7 (2)	C6—C8—C9—C10	−179.93 (12)
C4—N1—C1—C2	142.90 (15)	O3—C8—C9—C4	178.04 (13)
C5—N1—C1—C3	−111.89 (15)	C6—C8—C9—C4	−1.95 (19)
C4—N1—C1—C3	72.71 (17)	C4—C9—C10—C11	−0.6 (2)
N1—C1—C2—C3	−108.68 (16)	C8—C9—C10—C11	177.44 (13)
N1—C1—C3—C2	109.24 (15)	C9—C10—C11—F1	−178.59 (12)
C5—N1—C4—C9	−1.04 (19)	C9—C10—C11—C12	−0.8 (2)
C1—N1—C4—C9	174.39 (12)	C13—N2—C12—C17	−18.35 (19)
C5—N1—C4—C17	179.78 (12)	C16—N2—C12—C17	114.94 (15)
C1—N1—C4—C17	−4.79 (19)	C13—N2—C12—C11	159.17 (13)
C4—N1—C5—C6	−4.0 (2)	C16—N2—C12—C11	−67.54 (17)
C1—N1—C5—C6	−179.43 (13)	C10—C11—C12—C17	1.7 (2)
N1—C5—C6—C8	6.0 (2)	F1—C11—C12—C17	179.54 (12)
N1—C5—C6—C7	−170.79 (12)	C10—C11—C12—N2	−175.95 (13)
C5—C6—C7—O1	−39.6 (2)	F1—C11—C12—N2	1.8 (2)
C8—C6—C7—O1	143.59 (15)	C12—N2—C13—C14	−164.22 (12)
C5—C6—C7—O2	137.98 (14)	C16—N2—C13—C14	60.79 (14)
C8—C6—C7—O2	−38.8 (2)	C15—N3—C14—C13	54.62 (15)
C5—C6—C8—O3	177.16 (13)	N2—C13—C14—N3	−57.72 (15)
C7—C6—C8—O3	−6.1 (2)	C14—N3—C15—C16	−53.26 (15)
C5—C6—C8—C9	−2.85 (19)	C12—N2—C16—C15	162.40 (12)
C7—C6—C8—C9	173.88 (12)	C13—N2—C16—C15	−61.08 (15)
N1—C4—C9—C10	−178.10 (12)	N3—C15—C16—N2	56.20 (16)
C17—C4—C9—C10	1.1 (2)	N2—C12—C17—C4	176.32 (12)
N1—C4—C9—C8	3.9 (2)	C11—C12—C17—C4	−1.2 (2)
C17—C4—C9—C8	−176.89 (12)	N1—C4—C17—C12	179.02 (12)
O3—C8—C9—C10	0.1 (2)	C9—C4—C17—C12	−0.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O1	0.82	2.27	3.029 (4)	155
N3—H1A···O2^i	0.90	1.73	2.6209 (17)	171
N3—H1B···O3^ii	0.90	1.99	2.8247 (18)	154
N3—H1B···O2^ii	0.90	2.27	2.8422 (17)	121

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