Redetermination and invariom refinement of 1-cyclo-propyl-6-fluoro-4-oxo-7-(piperazin-4-ium-1-yl)-1,4-dihydro-quinoline-3-carboxyl-ate hexa-hydrate at 120 K.

The structure of the title compound, C(17)H(18)FN(3)O(3)·6H(2)O, has been redetermined at 120 K. An invariom refinement, a structural refinement using aspherical scattering factors from theoretically predicted multipole population parameters, yields accurate geometry and anisotropic displacement parameters, including hydrogen-bonding parameters. All potential hydrogen-bond donors and acceptors are involved in hydrogen bonding, forming an intricate three-dimensional network of N-H⋯O and O-H⋯O bonds.

Related literature

For related literature on the invariom refinement procedure, see: Dittrich et al. (2005 ▶); Hübschle et al. (2007 ▶); Hansen & Coppens (1978 ▶). For the original structure determination and background information on quinolone anti­bacterial agents, see: Turel et al. (1997 ▶); Turel (2002 ▶); Mitscher (2005 ▶).

Experimental

Crystal data

C17H18FN3O3·6H2O

M = 439.44

Triclinic,

a = 9.5079 (3) Å

b = 9.9437 (3) Å

c = 11.0391 (3) Å

α = 94.227 (2)°

β = 100.206 (2)°

γ = 91.327 (2)°

V = 1023.66 (6) Å3

Z = 2.0

Mo Kα radiation

μ = 0.12 mm−1

T = 120 K

0.30 × 0.25 × 0.03 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.918, T max = 0.996

35927 measured reflections

7766 independent reflections

6705 reflections with F > 3σ(F)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.032

S = 2.09

6705 reflections

391 parameters

All H-atom parameters refined

Δρmax = 0.22 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; method used to solve structure: from known coordinates (Turel et al., 1997 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶) and XD (Koritsánszky et al., 2003 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: XDCIF (Koritsánszky et al., 2003 ▶) and publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037409/bi2314sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037409/bi2314Isup2.hkl

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

C17H18FN3O3·6H2O	Z = 2.0
Mr = 439.44	F000 = 468
Triclinic, P1	Dx = 1.426 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 9.5079 (3) Å	Cell parameters from 9906 reflections
b = 9.9437 (3) Å	θ = 2.6–35.8º
c = 11.0391 (3) Å	µ = 0.12 mm−1
α = 94.227 (2)º	T = 120 K
β = 100.206 (2)º	Plate, colourless
γ = 91.327 (2)º	0.30 × 0.25 × 0.03 mm
V = 1023.66 (6) Å3

Bruker APEXII diffractometer	7766 independent reflections
Radiation source: Mo microsource	6705 reflections with F > 3σ(F)
Monochromator: graphite	Rint = 0.037
T = 120 K	θmax = 33.1º
ω scans	θmin = 2.1º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.918, Tmax = 0.996	k = −15→15
35927 measured reflections	l = 0→16

Refinement on F	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.024	All H-atom parameters refined
wR(F2) = 0.032	w1 = 1/[s2(Fo)]
S = 2.09	(Δ/σ)max < 0.001
6705 reflections	Δρmax = 0.22 e Å−3
391 parameters	Δρmin = −0.29 e Å−3
Primary atom site location: none	Extinction correction: none

	x	y	z	Uiso*/Ueq
F(1)	−0.33045 (4)	0.12852 (4)	0.58299 (3)	0.017
O(1)	0.40535 (4)	0.62476 (4)	0.78894 (4)	0.016
O(2)	0.20874 (4)	0.70663 (4)	0.84664 (4)	0.017
O(3)	−0.01084 (5)	0.50635 (4)	0.80861 (4)	0.018
O(41)	0.51207 (6)	0.36492 (5)	0.80865 (6)	0.032
O(51)	0.67335 (6)	0.70056 (6)	0.93720 (5)	0.026
O(61)	−0.12179 (6)	0.06543 (6)	−0.12561 (5)	0.028
O(71)	−0.05227 (6)	0.79577 (5)	0.91011 (5)	0.027
O(81)	−0.21443 (5)	0.44232 (6)	0.94044 (5)	0.024
O(91)	−0.35014 (5)	0.08636 (5)	0.00415 (4)	0.017
N(1)	0.17346 (5)	0.36898 (5)	0.51490 (4)	0.011
N(2)	−0.22506 (5)	0.04178 (5)	0.37452 (4)	0.011
N(3)	−0.37382 (5)	−0.12031 (5)	0.16130 (5)	0.012
C(1)	0.23877 (6)	0.33110 (6)	0.40859 (5)	0.012
C(2)	0.39731 (6)	0.31298 (7)	0.42941 (6)	0.018
C(3)	0.29514 (6)	0.19203 (6)	0.39590 (6)	0.016
C(4)	0.04233 (5)	0.31170 (5)	0.52812 (5)	0.01
C(5)	0.23769 (6)	0.46656 (5)	0.59958 (5)	0.011
C(6)	0.18357 (6)	0.51677 (5)	0.70044 (5)	0.011
C(7)	0.27219 (6)	0.62394 (5)	0.78547 (5)	0.012
C(8)	0.04741 (6)	0.46515 (6)	0.72033 (5)	0.012
C(9)	−0.02011 (5)	0.35741 (5)	0.62955 (5)	0.01
C(10)	−0.14985 (6)	0.29436 (6)	0.64428 (5)	0.012
C(11)	−0.21170 (6)	0.19255 (6)	0.56113 (5)	0.012
C(12)	−0.15499 (6)	0.14755 (5)	0.45515 (5)	0.011
C(13)	−0.14735 (6)	−0.01330 (6)	0.27971 (5)	0.012
C(14)	−0.22196 (6)	−0.14286 (6)	0.21485 (5)	0.013
C(15)	−0.44960 (6)	−0.06561 (6)	0.26046 (5)	0.013
C(16)	−0.37577 (6)	0.06451 (6)	0.32136 (5)	0.012
C(17)	−0.02664 (6)	0.20945 (5)	0.44071 (5)	0.011
H(311)	−0.4250 (10)	−0.2100 (10)	0.1250 (10)	0.043 (3)
H(312)	−0.3779 (9)	−0.0550 (9)	0.0933 (9)	0.027 (2)
H(11)	0.1918 (9)	0.3733 (8)	0.3296 (8)	0.029 (2)
H(21)	0.4516 (9)	0.3257 (8)	0.5233 (8)	0.029 (2)
H(22)	0.4485 (9)	0.3462 (9)	0.3602 (9)	0.037 (2)
H(31)	0.2831 (9)	0.1433 (9)	0.3068 (9)	0.033 (2)
H(32)	0.2849 (9)	0.1304 (9)	0.4675 (8)	0.035 (2)
H(51)	0.3399 (9)	0.5067 (9)	0.5852 (7)	0.028 (2)
H(101)	−0.1957 (9)	0.3228 (9)	0.7198 (8)	0.031 (2)
H(131)	−0.0424 (9)	−0.0394 (9)	0.3266 (8)	0.029 (2)
H(132)	−0.1367 (9)	0.0571 (9)	0.2100 (8)	0.028 (2)
H(141)	−0.1715 (9)	−0.1792 (9)	0.1422 (8)	0.030 (2)
H(142)	−0.2228 (9)	−0.2200 (9)	0.2761 (8)	0.028 (2)
H(151)	−0.4442 (9)	−0.1406 (9)	0.3245 (8)	0.034 (2)
H(152)	−0.5590 (10)	−0.0490 (10)	0.2190 (10)	0.039 (2)
H(161)	−0.3774 (9)	0.1389 (9)	0.2537 (8)	0.030 (2)
H(162)	−0.4302 (9)	0.0975 (8)	0.3918 (8)	0.031 (2)
H(171)	0.0170 (8)	0.1819 (8)	0.3589 (8)	0.022 (2)
H(411)	0.6040 (10)	0.3780 (10)	0.8550 (10)	0.039 (3)
H(412)	0.4720 (10)	0.4530 (10)	0.8050 (10)	0.041 (3)
H(511)	0.7020 (10)	0.6100 (10)	0.9510 (10)	0.041 (3)
H(512)	0.5850 (10)	0.6900 (10)	0.8910 (10)	0.039 (3)
H(611)	−0.0920 (10)	−0.0250 (10)	−0.1190 (10)	0.043 (3)
H(612)	−0.0550 (10)	0.1170 (10)	−0.0610 (10)	0.047 (3)
H(711)	0.0040 (10)	0.7320 (10)	0.8750 (10)	0.049 (3)
H(712)	−0.1410 (10)	0.7550 (10)	0.9080 (10)	0.045 (3)
H(811)	−0.1790 (10)	0.4090 (10)	1.0130 (10)	0.044 (3)
H(812)	−0.1370 (10)	0.4600 (10)	0.8990 (10)	0.040 (3)
H(911)	−0.2840 (10)	0.0710 (10)	−0.0460 (10)	0.032 (3)
H(912)	−0.3176 (9)	0.1646 (10)	0.0559 (9)	0.031 (2)

	U11	U22	U33	U12	U13	U23
F(1)	0.0139 (2)	0.0189 (2)	0.0175 (2)	−0.00660 (10)	0.00720 (10)	−0.00390 (10)
O(1)	0.0106 (2)	0.0146 (2)	0.0204 (2)	−0.00230 (10)	0.0016 (2)	−0.0033 (2)
O(2)	0.0155 (2)	0.0133 (2)	0.0198 (2)	−0.0025 (2)	0.0049 (2)	−0.0062 (2)
O(3)	0.0158 (2)	0.0208 (2)	0.0180 (2)	−0.0067 (2)	0.0095 (2)	−0.0096 (2)
O(41)	0.0217 (2)	0.0143 (2)	0.0567 (4)	−0.0022 (2)	0.0038 (2)	0.0000 (2)
O(51)	0.0192 (2)	0.0240 (3)	0.0313 (3)	−0.0029 (2)	−0.0015 (2)	−0.0065 (2)
O(61)	0.0268 (3)	0.0282 (3)	0.0281 (3)	0.0032 (2)	0.0103 (2)	0.0013 (2)
O(71)	0.0217 (2)	0.0201 (2)	0.0372 (3)	0.0010 (2)	0.0076 (2)	−0.0060 (2)
O(81)	0.0186 (2)	0.0314 (3)	0.0240 (3)	0.0036 (2)	0.0081 (2)	0.0086 (2)
O(91)	0.0157 (2)	0.0172 (2)	0.0161 (2)	−0.0035 (2)	0.0008 (2)	0.0002 (2)
N(1)	0.0100 (2)	0.0119 (2)	0.0094 (2)	−0.0008 (2)	0.0026 (2)	0.0000 (2)
N(2)	0.0087 (2)	0.0111 (2)	0.0125 (2)	−0.0006 (2)	0.0021 (2)	−0.0019 (2)
N(3)	0.0105 (2)	0.0127 (2)	0.0129 (2)	−0.0005 (2)	0.0007 (2)	−0.0020 (2)
C(1)	0.0107 (2)	0.0133 (2)	0.0121 (2)	−0.0001 (2)	0.0039 (2)	−0.0003 (2)
C(2)	0.0110 (2)	0.0197 (3)	0.0217 (3)	−0.0010 (2)	0.0069 (2)	−0.0033 (2)
C(3)	0.0140 (2)	0.0145 (3)	0.0196 (3)	0.0016 (2)	0.0053 (2)	−0.0019 (2)
C(4)	0.0087 (2)	0.0105 (2)	0.0107 (2)	−0.0005 (2)	0.0023 (2)	−0.0009 (2)
C(5)	0.0095 (2)	0.0107 (2)	0.0133 (2)	−0.0014 (2)	0.0028 (2)	−0.0007 (2)
C(6)	0.0097 (2)	0.0102 (2)	0.0123 (2)	−0.0016 (2)	0.0026 (2)	−0.0019 (2)
C(7)	0.0108 (2)	0.0099 (2)	0.0134 (2)	−0.0012 (2)	0.0022 (2)	−0.0012 (2)
C(8)	0.0105 (2)	0.0117 (2)	0.0119 (2)	−0.0011 (2)	0.0033 (2)	−0.0032 (2)
C(9)	0.0092 (2)	0.0106 (2)	0.0111 (2)	−0.0010 (2)	0.0024 (2)	−0.0019 (2)
C(10)	0.0101 (2)	0.0139 (2)	0.0130 (2)	−0.0022 (2)	0.0045 (2)	−0.0028 (2)
C(11)	0.0100 (2)	0.0133 (2)	0.0127 (2)	−0.0022 (2)	0.0041 (2)	−0.0018 (2)
C(12)	0.0089 (2)	0.0109 (2)	0.0112 (2)	−0.0006 (2)	0.0025 (2)	−0.0016 (2)
C(13)	0.0092 (2)	0.0122 (2)	0.0137 (2)	−0.0001 (2)	0.0026 (2)	−0.0025 (2)
C(14)	0.0111 (2)	0.0114 (2)	0.0153 (3)	0.0009 (2)	0.0006 (2)	−0.0022 (2)
C(15)	0.0096 (2)	0.0145 (3)	0.0136 (2)	−0.0019 (2)	0.0020 (2)	−0.0016 (2)
C(16)	0.0090 (2)	0.0121 (2)	0.0146 (3)	0.0007 (2)	0.0016 (2)	−0.0018 (2)
C(17)	0.0090 (2)	0.0111 (2)	0.0118 (2)	−0.0013 (2)	0.0019 (2)	−0.0016 (2)

F(1)—C(11)	1.3504 (6)	C(2)—C(3)	1.5098 (9)
O(1)—C(7)	1.2595 (7)	C(2)—H(21)	1.070 (9)
O(2)—C(7)	1.2577 (7)	C(2)—H(22)	1.045 (10)
O(3)—C(8)	1.2520 (7)	C(3)—H(31)	1.050 (9)
O(41)—H(411)	0.931 (11)	C(3)—H(32)	1.051 (9)
O(41)—H(412)	0.965 (11)	C(4)—C(9)	1.4093 (8)
O(51)—H(511)	0.957 (11)	C(4)—C(17)	1.4125 (8)
O(51)—H(512)	0.903 (11)	C(5)—C(6)	1.3738 (8)
O(61)—H(611)	0.948 (12)	C(5)—H(51)	1.084 (9)
O(61)—H(612)	0.969 (12)	C(6)—C(7)	1.5023 (8)
O(71)—H(711)	0.941 (12)	C(6)—C(8)	1.4400 (7)
O(71)—H(712)	0.922 (11)	C(8)—C(9)	1.4650 (8)
O(81)—H(811)	0.904 (11)	C(9)—C(10)	1.4110 (7)
O(81)—H(812)	0.952 (11)	C(10)—C(11)	1.3629 (8)
O(91)—H(911)	0.919 (10)	C(10)—H(101)	1.031 (9)
O(91)—H(912)	0.943 (10)	C(11)—C(12)	1.4205 (8)
N(1)—C(1)	1.4523 (7)	C(12)—C(17)	1.3933 (7)
N(1)—C(4)	1.3940 (7)	C(13)—C(14)	1.5222 (8)
N(1)—C(5)	1.3509 (7)	C(13)—H(131)	1.086 (9)
N(2)—C(12)	1.4006 (7)	C(13)—H(132)	1.094 (9)
N(2)—C(13)	1.4663 (7)	C(14)—H(141)	1.052 (9)
N(3)—H(311)	1.026 (12)	C(14)—H(142)	1.060 (9)
N(3)—H(312)	1.025 (10)	C(15)—C(16)	1.5103 (8)
N(2)—C(16)	1.4782 (7)	C(15)—H(151)	1.061 (9)
N(3)—C(14)	1.4889 (7)	C(15)—H(152)	1.084 (10)
N(3)—C(15)	1.4910 (8)	C(16)—H(161)	1.087 (9)
C(1)—C(2)	1.5010 (8)	C(16)—H(162)	1.046 (9)
C(1)—C(3)	1.5004 (8)	C(17)—H(171)	1.079 (8)
C(1)—H(11)	1.030 (9)
H(411)—O(41)—H(412)	105.7 (8)	O(3)—C(8)—C(9)	121.14 (5)
H(511)—O(51)—H(512)	104.1 (8)	C(6)—C(8)—C(9)	115.11 (5)
H(611)—O(61)—H(612)	103.5 (8)	C(4)—C(9)—C(8)	121.95 (5)
H(711)—O(71)—H(712)	107.6 (8)	C(4)—C(9)—C(10)	118.27 (5)
H(811)—O(81)—H(812)	108.2 (8)	C(8)—C(9)—C(10)	119.77 (5)
H(911)—O(91)—H(912)	106.5 (7)	C(9)—C(10)—C(11)	119.92 (5)
C(1)—N(1)—C(4)	121.37 (5)	C(9)—C(10)—H(101)	120.0 (5)
C(1)—N(1)—C(5)	119.24 (4)	C(11)—C(10)—H(101)	120.1 (5)
C(4)—N(1)—C(5)	119.30 (5)	F(1)—C(11)—C(10)	118.14 (5)
C(12)—N(2)—C(13)	116.04 (4)	F(1)—C(11)—C(12)	118.45 (5)
H(311)—N(3)—H(312)	109.3 (7)	C(10)—C(11)—C(12)	123.38 (5)
N(1)—C(1)—C(2)	118.16 (5)	N(2)—C(12)—C(11)	119.72 (5)
N(1)—C(1)—C(3)	118.70 (5)	N(2)—C(12)—C(17)	123.50 (5)
N(1)—C(1)—H(11)	113.4 (5)	C(11)—C(12)—C(17)	116.72 (5)
C(2)—C(1)—C(3)	60.40 (4)	N(2)—C(13)—C(14)	110.41 (4)
C(2)—C(1)—H(11)	118.3 (5)	N(2)—C(13)—H(131)	107.3 (4)
C(3)—C(1)—H(11)	118.1 (5)	N(2)—C(13)—H(132)	113.1 (4)
C(1)—C(2)—C(3)	59.78 (4)	C(14)—C(13)—H(131)	107.3 (4)
C(1)—C(2)—H(21)	116.0 (4)	C(14)—C(13)—H(132)	108.5 (4)
C(1)—C(2)—H(22)	114.8 (5)	H(131)—C(13)—H(132)	110.1 (6)
C(3)—C(2)—H(21)	116.1 (4)	C(13)—C(14)—H(141)	111.0 (5)
C(3)—C(2)—H(22)	117.3 (5)	C(13)—C(14)—H(142)	112.0 (4)
H(21)—C(2)—H(22)	119.0 (6)	H(141)—C(14)—H(142)	108.1 (6)
C(1)—C(3)—C(2)	59.82 (4)	N(3)—C(14)—C(13)	111.14 (5)
C(1)—C(3)—H(31)	117.8 (5)	N(3)—C(14)—H(141)	107.5 (4)
C(1)—C(3)—H(32)	115.7 (5)	N(3)—C(14)—H(142)	106.9 (4)
C(2)—C(3)—H(31)	118.9 (5)	N(3)—C(15)—C(16)	109.86 (5)
C(2)—C(3)—H(32)	116.4 (5)	N(3)—C(15)—H(151)	105.8 (5)
H(31)—C(3)—H(32)	116.3 (7)	N(3)—C(15)—H(152)	108.2 (5)
N(1)—C(4)—C(9)	119.07 (5)	C(16)—C(15)—H(151)	110.8 (5)
N(1)—C(4)—C(17)	120.24 (5)	C(16)—C(15)—H(152)	111.0 (5)
C(9)—C(4)—C(17)	120.69 (5)	H(151)—C(15)—H(152)	111.1 (7)
N(1)—C(5)—C(6)	125.09 (5)	N(2)—C(16)—C(15)	110.46 (5)
N(1)—C(5)—H(51)	116.1 (4)	N(2)—C(16)—H(161)	108.3 (4)
C(6)—C(5)—H(51)	118.8 (4)	N(2)—C(16)—H(162)	109.6 (5)
C(5)—C(6)—C(7)	117.23 (5)	C(15)—C(16)—H(161)	110.0 (4)
C(5)—C(6)—C(8)	119.45 (5)	C(15)—C(16)—H(162)	107.3 (5)
C(7)—C(6)—C(8)	123.32 (5)	H(161)—C(16)—H(162)	111.2 (6)
O(1)—C(7)—O(2)	124.85 (5)	C(4)—C(17)—C(12)	120.94 (5)
O(1)—C(7)—C(6)	117.03 (5)	C(4)—C(17)—H(171)	120.0 (4)
O(2)—C(7)—C(6)	118.12 (5)	C(12)—C(17)—H(171)	119.0 (4)
O(3)—C(8)—C(6)	123.75 (5)
C(4)—N(1)—C(1)—C(2)	−139.1 (1)	N(1)—C(4)—C(17)—C(12)	177.5 (1)
C(4)—N(1)—C(1)—C(3)	−69.3 (1)	N(1)—C(4)—C(17)—H(171)	−5.7 (5)
C(1)—N(1)—C(4)—C(9)	−176.5 (1)	C(17)—C(4)—C(9)—C(8)	−178.7 (1)
C(1)—N(1)—C(4)—C(17)	3.4 (1)	C(17)—C(4)—C(9)—C(10)	2.7 (1)
C(4)—N(1)—C(1)—H(11)	76.0 (6)	C(9)—C(4)—C(17)—C(12)	−2.6 (1)
C(5)—N(1)—C(1)—C(2)	44.2 (1)	C(9)—C(4)—C(17)—H(171)	174.2 (5)
C(5)—N(1)—C(1)—C(3)	114.0 (1)	N(1)—C(5)—C(6)—C(7)	179.0 (1)
C(1)—N(1)—C(5)—C(6)	176.3 (1)	N(1)—C(5)—C(6)—C(8)	−0.6 (1)
C(5)—N(1)—C(1)—H(11)	−100.6 (6)	H(51)—C(5)—C(6)—C(7)	−0.8 (6)
C(1)—N(1)—C(5)—H(51)	−3.9 (6)	H(51)—C(5)—C(6)—C(8)	179.5 (6)
C(4)—N(1)—C(5)—C(6)	−0.4 (1)	C(5)—C(6)—C(7)—O(1)	−26.4 (1)
C(5)—N(1)—C(4)—C(9)	0.1 (1)	C(5)—C(6)—C(7)—O(2)	152.9 (1)
C(5)—N(1)—C(4)—C(17)	−179.9 (1)	C(5)—C(6)—C(8)—O(3)	−178.9 (1)
C(4)—N(1)—C(5)—H(51)	179.4 (6)	C(5)—C(6)—C(8)—C(9)	1.8 (1)
C(13)—N(2)—C(12)—C(11)	−170.1 (1)	C(8)—C(6)—C(7)—O(1)	153.3 (1)
C(12)—N(2)—C(13)—C(14)	169.4 (1)	C(8)—C(6)—C(7)—O(2)	−27.5 (1)
C(13)—N(2)—C(12)—C(17)	7.0 (1)	C(7)—C(6)—C(8)—O(3)	1.4 (1)
C(12)—N(2)—C(13)—H(131)	52.8 (5)	C(7)—C(6)—C(8)—C(9)	−177.9 (1)
C(12)—N(2)—C(13)—H(132)	−68.8 (5)	O(3)—C(8)—C(9)—C(4)	178.6 (1)
N(1)—C(1)—C(2)—C(3)	108.8 (1)	O(3)—C(8)—C(9)—C(10)	−2.9 (1)
N(1)—C(1)—C(2)—H(21)	2.4 (6)	C(6)—C(8)—C(9)—C(4)	−2.1 (1)
N(1)—C(1)—C(2)—H(22)	−142.7 (6)	C(6)—C(8)—C(9)—C(10)	176.4 (1)
N(1)—C(1)—C(3)—C(2)	−107.9 (1)	C(4)—C(9)—C(10)—C(11)	−0.3 (1)
N(1)—C(1)—C(3)—H(31)	143.1 (6)	C(4)—C(9)—C(10)—H(101)	177.3 (6)
N(1)—C(1)—C(3)—H(32)	−1.1 (6)	C(8)—C(9)—C(10)—C(11)	−178.9 (1)
C(2)—C(1)—C(3)—C(2)	0.0 (1)	C(8)—C(9)—C(10)—H(101)	−1.3 (6)
C(3)—C(1)—C(2)—C(3)	0.0 (1)	C(9)—C(10)—C(11)—F(1)	175.5 (1)
C(3)—C(1)—C(2)—H(21)	−106.5 (6)	C(9)—C(10)—C(11)—C(12)	−2.3 (1)
C(3)—C(1)—C(2)—H(22)	108.4 (6)	H(101)—C(10)—C(11)—F(1)	−2.1 (6)
C(2)—C(1)—C(3)—H(31)	−109.0 (6)	H(101)—C(10)—C(11)—C(12)	−179.9 (6)
C(2)—C(1)—C(3)—H(32)	106.9 (6)	F(1)—C(11)—C(12)—N(2)	1.9 (1)
H(11)—C(1)—C(2)—C(3)	−108.1 (6)	F(1)—C(11)—C(12)—C(17)	−175.4 (1)
H(11)—C(1)—C(2)—H(21)	145.5 (8)	C(10)—C(11)—C(12)—N(2)	179.8 (1)
H(11)—C(1)—C(2)—H(22)	0.4 (8)	C(10)—C(11)—C(12)—C(17)	2.4 (1)
H(11)—C(1)—C(3)—C(2)	108.3 (6)	N(2)—C(12)—C(17)—C(4)	−177.2 (1)
H(11)—C(1)—C(3)—H(31)	−0.7 (8)	N(2)—C(12)—C(17)—H(171)	6.0 (5)
H(11)—C(1)—C(3)—H(32)	−144.8 (8)	C(11)—C(12)—C(17)—C(4)	0.1 (1)
C(1)—C(2)—C(3)—C(1)	0.0 (1)	C(11)—C(12)—C(17)—H(171)	−176.8 (5)
C(1)—C(2)—C(3)—H(31)	107.1 (6)	N(2)—C(13)—C(14)—H(141)	175.7 (6)
C(1)—C(2)—C(3)—H(32)	−105.8 (6)	N(2)—C(13)—C(14)—H(142)	−63.4 (5)
H(21)—C(2)—C(3)—C(1)	106.2 (6)	H(131)—C(13)—C(14)—H(141)	−67.7 (7)
H(21)—C(2)—C(3)—H(31)	−146.6 (8)	H(131)—C(13)—C(14)—H(142)	53.2 (7)
H(21)—C(2)—C(3)—H(32)	0.4 (8)	H(132)—C(13)—C(14)—H(141)	51.3 (7)
H(22)—C(2)—C(3)—C(1)	−104.2 (6)	H(132)—C(13)—C(14)—H(142)	172.2 (7)
H(22)—C(2)—C(3)—H(31)	2.9 (9)	H(151)—C(15)—C(16)—H(161)	177.2 (7)
H(22)—C(2)—C(3)—H(32)	150.0 (8)	H(151)—C(15)—C(16)—H(162)	−61.7 (8)
N(1)—C(4)—C(9)—C(8)	1.2 (1)	H(152)—C(15)—C(16)—H(161)	−58.9 (8)
N(1)—C(4)—C(9)—C(10)	−177.4 (1)	H(152)—C(15)—C(16)—H(162)	62.2 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N(3)—H(311)···O(51)i	1.025 (10)	2.533 (10)	3.0458 (8)	110.4 (7)
N(3)—H(311)···O(41)ii	1.025 (10)	1.979 (10)	2.8063 (7)	135.8 (9)
N(3)—H(312)···O(91)	1.024 (9)	1.814 (9)	2.8153 (7)	164.6 (8)
O(41)—H(412)···O(1)	0.964 (10)	1.845 (10)	2.8064 (6)	175.2 (9)
O(41)—H(411)···O(81)iii	0.932 (10)	1.887 (10)	2.8055 (8)	168.0 (9)
O(51)—H(511)···O(81)iii	0.962 (10)	1.868 (10)	2.8032 (8)	163.4 (9)
O(51)—H(512)···O(1)	0.902 (10)	1.941 (10)	2.8265 (7)	167.1 (9)
O(61)—H(611)···O(71)iv	0.953 (10)	1.869 (10)	2.8150 (8)	171.6 (9)
O(61)—H(612)···O(71)v	0.972 (10)	1.927 (11)	2.8842 (8)	167.8 (9)
O(71)—H(711)···O(2)	0.944 (10)	2.044 (10)	2.8392 (7)	140.8 (8)
O(71)—H(711)···O(3)	0.944 (10)	2.302 (10)	3.0702 (7)	138.1 (8)
O(71)—H(712)···O(51)vi	0.923 (10)	1.922 (10)	2.8272 (8)	166.2 (9)
O(81)—H(811)···O(2)vii	0.902 (11)	2.050 (10)	2.8624 (7)	149.1 (9)
O(81)—H(811)···O(3)vii	0.902 (11)	2.504 (10)	3.1874 (7)	132.9 (8)
O(81)—H(812)···O(3)	0.953 (10)	1.764 (10)	2.7104 (7)	171.8 (9)
O(91)—H(911)···O(61)	0.917 (10)	1.906 (10)	2.8085 (7)	167.9 (9)
O(91)—H(912)···O(2)v	0.942 (10)	1.791 (10)	2.7102 (6)	164.1 (8)

Atom label	Invariom assigned	Model compound
F1	F1c	fluoromethane
O1, O2, O3	O1.5c[1.5o1c]-	acetic acid anion
O41–O91	O1h1h	water
N1, N2	N1c1c1c	trimethylamine
N3	N1c1c1h1h+	N,N-dimethylammonium
C1	C1n1c1c1h	2-aminopropane
C2, C3	C1c1c1h1h	propane
C4	C1.5c[1.5c1c]1.5c[1.5c1h]1n	o-methylaniline
C5	C1.5n[1.5c1c]1.5c[1.5c1c]1h+	N-methyl-3-methylpyridinium
C6	C1.5c[1.5n1h]1.5c[1.5c1o]1c+	3-methyl-4-hydroxypyridinium
C7	C1.5o1.5o1c-	acetic acid anion
C8	C2o1c1c	acetone
C9	C1.5c[1.5c1n]1.5c[1.5c1h]1c	o-methylaniline
C10	C1.5c[1.5c1f]1.5c[1.5c1c]1h	1-fluoro-3-methylbenzene
C11	C1.5c[1.5c1n]1.5c[1.5c1h]1f	2-fluoroaniline
C12	C1.5c[1.5c1f]1.5c[1.5c1h]1n	2-fluoroaniline
C13–C16	C1n1c1h1h	aminoethane
C17	C1.5c[1.5c1n]1.5c[1.5c1n]1h	m-phenylenediamine
H312, H322	H1n[1c1c1h]+	dimethylammonium
H11	H1c[1n1c1c]	2-aminopropane
H21–H32	H1c[1c1c1h]	propane
H51	H1c[1.5n1.5c]	pyridine
H101, H171	H1c[1.5c1.5c]	benzene
H131–H162	H1c[1n1c1h]	aminoethane
H411–H912	H1o[1h]	water

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H311⋯O51i	1.02 (1)	2.53 (1)	3.0458 (8)	110 (1)
N3—H311⋯O41ii	1.02 (1)	1.98 (1)	2.8063 (7)	136 (1)
N3—H312⋯O91	1.02 (1)	1.81 (1)	2.8153 (7)	165 (1)
O41—H412⋯O1	0.96 (1)	1.84 (1)	2.8064 (6)	175 (1)
O41—H411⋯O81iii	0.93 (1)	1.89 (1)	2.8055 (8)	168 (1)
O51—H511⋯O81iii	0.96 (1)	1.87 (1)	2.8032 (8)	163 (1)
O51—H512⋯O1	0.90 (1)	1.94 (1)	2.8265 (7)	167 (1)
O61—H611⋯O71iv	0.95 (1)	1.87 (1)	2.8150 (8)	172 (1)
O61—H612⋯O71v	0.97 (1)	1.93 (1)	2.8842 (8)	168 (1)
O71—H711⋯O2	0.94 (1)	2.04 (1)	2.8392 (7)	141 (1)
O71—H711⋯O3	0.94 (1)	2.30 (1)	3.0702 (7)	138 (1)
O71—H712⋯O51vi	0.92 (1)	1.92 (1)	2.8272 (8)	166 (1)
O81—H811⋯O2vii	0.90 (1)	2.05 (1)	2.8624 (7)	149 (1)
O81—H811⋯O3vii	0.90 (1)	2.50 (1)	3.1874 (7)	133 (1)
O81—H812⋯O3	0.95 (1)	1.76 (1)	2.7104 (7)	172 (1)
O91—H911⋯O61	0.92 (1)	1.91 (1)	2.8085 (7)	168 (1)
O91—H912⋯O2v	0.94 (1)	1.79 (1)	2.7102 (6)	164 (1)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .

Table 2

Invarioms and model compounds used for aspherical refinement of the title compound

Atom label	Invariom assigned	Model compound
F1	F1c	fluoromethane
O1, O2, O3	O1.5c[1.5o1c]−	acetic acid anion
O41–O91	O1h1h	water
N1, N2	N1c1c1c	trimethylamine
N3	N1c1c1h1h+	N,N-dimethylammonium
C1	C1n1c1c1h	2-aminopropane
C2, C3	C1c1c1h1h	propane
C4	C1.5c[1.5c1c]1.5c[1.5c1h]1n	o-methylaniline
C5	C1.5n[1.5c1c]1.5c[1.5c1c]1h+	N-meth­yl-3-methylpyridinium
C6	C1.5c[1.5n1h]1.5c[1.5c1o]1c+	3-meth­yl-4-hydroxypyridinium
C7	C1.5o1.5o1c−	acetic acid anion
C8	C2o1c1c	acetone
C9	C1.5c[1.5c1n]1.5c[1.5c1h]1c	o-methylaniline
C10	C1.5c[1.5c1f]1.5c[1.5c1c]1h	1-fluoro-3-methylbenzene
C11	C1.5c[1.5c1n]1.5c[1.5c1h]1f	2-fluoroaniline
C12	C1.5c[1.5c1f]1.5c[1.5c1h]1n	2-fluoroaniline
C13–C16	C1n1c1h1h	aminoethane
C17	C1.5c[1.5c1n]1.5c[1.5c1n]1h	m-phenylenediamine
H312, H322	H1n[1c1c1h]+	dimethylammonium
H11	H1c[1n1c1c]	2-aminopropane
H21–H32	H1c[1c1c1h]	propane
H51	H1c[1.5n1.5c]	pyridine
H101, H171	H1c[1.5c1.5c]	benzene
H131–H162	H1c[1n1c1h]	aminoethane
H411–H912	H1o[1h]	water