Bis(mefloquinium) butane­dioate ethanol monosolvate: crystal structure and Hirshfeld surface analysis

Wardell, J.L.; Jotani, M.M.; Tiekink, E.R.T.

doi:10.1107/S2056989019009654

Bis(mefloquinium) butanedioate ethanol monosolvate: crystal structure and Hirshfeld surface analysis

J. L. Wardell, M. M. Jotani and E. R. T. Tiekink

As the piperidin-1-ium group is nearly orthogonal to the quinolinyl residue in each of the two independent cations of the title salt solvate, these cations are L-shaped. Supramolecular chains arise in the crystal as a result of charge-assisted O—H

O and N—H

O hydrogen bonding.

Keywords: crystal structure; mefloquine; salt; hydrogen bonding; Hirshfeld surface analysis.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019009654/hb7838sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989019009654/hb7838Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989019009654/hb7838Isup3.cml Supplementary material

CCDC reference: 1938793

checkCIF report

Key indicators

Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.004 Å
R factor = 0.074
wR factor = 0.180
Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT910_ALERT_3_B Missing # of FCF Reflection(s) Below Theta(Min).         15 Note

Author Response: If there are "missing" reflections, they are below theta(min) and were probably not collected. Theta(min) in this experiment with Mo-Kalpha radiation was 2.9 deg. which, while a little high, is not excessively so.


Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C10 Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00429 Ang.
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C39      - C40      .       1.39 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
              C17 H17 F6 N2 O
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     10.371 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.472 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         10 Report
PLAT977_ALERT_2_C Check Negative Difference Density on H39B             -0.39 eA-3

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         12 Note
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT242_ALERT_2_G Low    'MainMol' Ueq as Compared to Neighbors of        C11 Check
PLAT242_ALERT_2_G Low    'MainMol' Ueq as Compared to Neighbors of        C27 Check
PLAT242_ALERT_2_G Low    'MainMol' Ueq as Compared to Neighbors of        C28 Check
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          2 Note
              C17 H17 F6 N2 O
PLAT793_ALERT_4_G Model has Chirality at C12         (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C13         (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C29         (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C30         (Centro SPGR)          S Verify
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          7 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         70 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         10 Info

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

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

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

2-{[2,8-Bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium butanedioate ethanol monosolvate top

Crystal data top

2C₁₇H₁₇F₆N₂O⁺·C₄H₄O₄²⁻·C₂H₆O	Z = 2
M_r = 920.79	F(000) = 952
Triclinic, P1	D_x = 1.467 Mg m⁻³
a = 10.0405 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.6482 (4) Å	Cell parameters from 32862 reflections
c = 14.6547 (4) Å	θ = 2.9–27.5°
α = 100.745 (1)°	µ = 0.14 mm⁻¹
β = 93.830 (2)°	T = 120 K
γ = 98.497 (2)°	Plate, colourless
V = 2084.41 (9) Å³	0.42 × 0.05 × 0.03 mm

Data collection top

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer	9543 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode	6505 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.085
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.6°, θ_min = 2.9°
φ & ω scans	h = −12→13
Absorption correction: multi-scan (SADABS;Sheldrick, 2007)	k = −18→19
T_min = 0.849, T_max = 1.000	l = −19→19
42885 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.074	Hydrogen site location: mixed
wR(F²) = 0.180	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0525P)² + 4.9226P] where P = (F_o² + 2F_c²)/3
9543 reflections	(Δ/σ)_max < 0.001
590 parameters	Δρ_max = 0.60 e Å⁻³
7 restraints	Δρ_min = −0.58 e Å⁻³

Special details top

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.

Refinement. Owing to poor agreement, possibly to interference from the beam-stop, one reflection, i.e. (0 -1 2), was omitted from the final cycles of refinement.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
F1	0.2808 (2)	0.67260 (18)	0.16134 (18)	0.0504 (7)
F2	0.2712 (2)	0.65790 (19)	0.01402 (19)	0.0506 (7)
F3	0.2412 (2)	0.53596 (15)	0.07419 (19)	0.0430 (6)
F4	−0.1087 (2)	0.38548 (14)	0.16771 (16)	0.0344 (5)
F5	−0.03229 (19)	0.48942 (14)	0.29119 (15)	0.0319 (5)
F6	−0.2296 (2)	0.40671 (14)	0.28320 (16)	0.0364 (5)
O1	−0.0896 (2)	0.82971 (15)	−0.04003 (16)	0.0212 (5)
H1O	−0.061 (4)	0.869 (2)	0.0096 (16)	0.032*
N1	−0.0028 (2)	0.57189 (18)	0.12924 (19)	0.0207 (6)
N2	−0.3489 (3)	0.78367 (18)	−0.13680 (19)	0.0190 (5)
H1N	−0.289 (3)	0.8273 (18)	−0.152 (2)	0.023*
H2N	−0.390 (3)	0.811 (2)	−0.0906 (17)	0.023*
C1	0.0642 (3)	0.6271 (2)	0.0803 (2)	0.0198 (6)
C2	0.0089 (3)	0.6897 (2)	0.0331 (2)	0.0190 (6)
H2	0.0631	0.7264	−0.0019	0.023*
C3	−0.1251 (3)	0.6968 (2)	0.0384 (2)	0.0188 (6)
C4	−0.2021 (3)	0.6417 (2)	0.0930 (2)	0.0181 (6)
C5	−0.3393 (3)	0.6472 (2)	0.1083 (2)	0.0223 (7)
H5	−0.3852	0.6885	0.0799	0.027*
C6	−0.4056 (3)	0.5940 (2)	0.1630 (2)	0.0237 (7)
H6	−0.4971	0.5989	0.1728	0.028*
C7	−0.3403 (3)	0.5318 (2)	0.2053 (3)	0.0260 (7)
H7	−0.3881	0.4952	0.2435	0.031*
C8	−0.2090 (3)	0.5233 (2)	0.1922 (2)	0.0217 (7)
C9	−0.1351 (3)	0.5793 (2)	0.1366 (2)	0.0195 (6)
C10	0.2142 (3)	0.6225 (2)	0.0822 (2)	0.0244 (7)
C11	−0.1435 (3)	0.4521 (2)	0.2331 (3)	0.0259 (7)
C12	−0.1883 (3)	0.7644 (2)	−0.0125 (2)	0.0184 (6)
H12	−0.2441	0.8000	0.0309	0.022*
C13	−0.2802 (3)	0.7122 (2)	−0.1001 (2)	0.0176 (6)
H13	−0.3506	0.6652	−0.0815	0.021*
C14	−0.4440 (3)	0.7429 (2)	−0.2226 (2)	0.0263 (7)
H14A	−0.4816	0.7940	−0.2457	0.032*
H14B	−0.5202	0.6991	−0.2071	0.032*
C15	−0.3715 (4)	0.6904 (3)	−0.2983 (2)	0.0295 (8)
H15A	−0.3033	0.7359	−0.3196	0.035*
H15B	−0.4376	0.6596	−0.3524	0.035*
C16	−0.3015 (3)	0.6160 (2)	−0.2630 (2)	0.0262 (7)
H16A	−0.3704	0.5665	−0.2484	0.031*
H16B	−0.2501	0.5861	−0.3123	0.031*
C17	−0.2054 (3)	0.6606 (2)	−0.1756 (2)	0.0201 (6)
H17A	−0.1649	0.6110	−0.1517	0.024*
H17B	−0.1312	0.7056	−0.1918	0.024*
F7	−0.6032 (3)	0.6297 (2)	0.3672 (3)	0.0874 (12)
F8	−0.6420 (2)	0.7695 (2)	0.3979 (2)	0.0572 (8)
F9	−0.5432 (2)	0.7145 (2)	0.50201 (19)	0.0670 (9)
F10	−0.1334 (2)	0.67918 (15)	0.55849 (15)	0.0343 (5)
F11	−0.1959 (2)	0.55632 (14)	0.44945 (16)	0.0371 (5)
F12	0.0147 (2)	0.60063 (14)	0.49868 (15)	0.0332 (5)
O2	−0.4008 (2)	0.92583 (16)	0.18909 (16)	0.0236 (5)
H2O	−0.424 (4)	0.897 (2)	0.1338 (12)	0.035*
N3	−0.3160 (3)	0.71100 (19)	0.4089 (2)	0.0229 (6)
N4	−0.1656 (3)	1.06682 (18)	0.20532 (19)	0.0186 (5)
H3N	−0.240 (2)	1.071 (2)	0.172 (2)	0.022*
H4N	−0.114 (3)	1.036 (2)	0.168 (2)	0.022*
C18	−0.4157 (3)	0.7498 (2)	0.3795 (2)	0.0239 (7)
C19	−0.4077 (3)	0.8153 (2)	0.3206 (2)	0.0221 (7)
H19	−0.4848	0.8413	0.3036	0.027*
C20	−0.2853 (3)	0.8408 (2)	0.2883 (2)	0.0188 (6)
C21	−0.1731 (3)	0.7995 (2)	0.3149 (2)	0.0188 (6)
C22	−0.0438 (3)	0.8172 (2)	0.2819 (2)	0.0191 (6)
H22	−0.0287	0.8594	0.2402	0.023*
C23	0.0591 (3)	0.7740 (2)	0.3097 (2)	0.0229 (7)
H23	0.1448	0.7858	0.2864	0.027*
C24	0.0399 (3)	0.7124 (2)	0.3722 (2)	0.0224 (7)
H24	0.1126	0.6831	0.3907	0.027*
C25	−0.0821 (3)	0.6942 (2)	0.4067 (2)	0.0223 (7)
C26	−0.1939 (3)	0.7360 (2)	0.3771 (2)	0.0191 (6)
C27	−0.5505 (3)	0.7155 (3)	0.4130 (3)	0.0339 (8)
C28	−0.1002 (3)	0.6326 (2)	0.4778 (2)	0.0259 (7)
C29	−0.2730 (3)	0.9119 (2)	0.2244 (2)	0.0182 (6)
H29	−0.2221	0.8882	0.1710	0.022*
C30	−0.1964 (3)	1.0076 (2)	0.2770 (2)	0.0187 (6)
H30	−0.1091	0.9978	0.3076	0.022*
C31	−0.0944 (3)	1.1651 (2)	0.2457 (2)	0.0243 (7)
H31A	−0.0841	1.2015	0.1953	0.029*
H31B	−0.0029	1.1628	0.2739	0.029*
C32	−0.1729 (3)	1.2135 (2)	0.3186 (3)	0.0291 (8)
H32A	−0.2611	1.2213	0.2891	0.035*
H32B	−0.1223	1.2768	0.3467	0.035*
C33	−0.1966 (4)	1.1559 (2)	0.3949 (3)	0.0309 (8)
H33A	−0.1087	1.1505	0.4265	0.037*
H33B	−0.2494	1.1880	0.4420	0.037*
C34	−0.2739 (3)	1.0578 (2)	0.3511 (2)	0.0253 (7)
H34A	−0.2880	1.0202	0.4002	0.030*
H34B	−0.3638	1.0634	0.3226	0.030*
O3	0.3721 (2)	0.87780 (16)	−0.09688 (16)	0.0245 (5)
O4	0.5232 (2)	0.85378 (16)	0.00986 (16)	0.0246 (5)
O5	0.1931 (2)	1.05633 (15)	0.18195 (15)	0.0217 (5)
O6	0.0086 (2)	0.96016 (15)	0.10987 (16)	0.0215 (5)
C35	0.4142 (3)	0.8829 (2)	−0.0146 (2)	0.0194 (6)
C36	0.3374 (3)	0.9243 (2)	0.0649 (2)	0.0212 (6)
H36A	0.3096	0.8752	0.1011	0.025*
H36B	0.3993	0.9762	0.1072	0.025*
C37	0.2127 (3)	0.9620 (2)	0.0338 (2)	0.0188 (6)
H37A	0.2407	1.0150	0.0024	0.023*
H37B	0.1535	0.9118	−0.0123	0.023*
C38	0.1328 (3)	0.9955 (2)	0.1142 (2)	0.0176 (6)
O7	0.1253 (3)	1.0539 (3)	0.3588 (2)	0.0587 (9)
H7O	0.147 (6)	1.052 (4)	0.3036 (17)	0.088*
C39	0.2349 (6)	1.0663 (5)	0.4209 (4)	0.083 (2)
H39A	0.2025	1.0473	0.4780	0.100*
H39B	0.2682	1.1349	0.4375	0.100*
C40	0.3465 (6)	1.0231 (7)	0.4013 (4)	0.105 (3)
H40A	0.3264	0.9569	0.4070	0.158*
H40B	0.4242	1.0552	0.4456	0.158*
H40C	0.3679	1.0265	0.3377	0.158*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0210 (11)	0.0686 (16)	0.0492 (15)	0.0145 (10)	−0.0092 (10)	−0.0207 (13)
F2	0.0212 (11)	0.0813 (18)	0.0645 (17)	0.0170 (11)	0.0168 (10)	0.0419 (15)
F3	0.0250 (11)	0.0294 (11)	0.0778 (18)	0.0147 (9)	0.0100 (11)	0.0087 (11)
F4	0.0393 (12)	0.0239 (10)	0.0413 (13)	0.0132 (8)	0.0039 (9)	0.0037 (9)
F5	0.0298 (11)	0.0327 (11)	0.0343 (12)	0.0066 (8)	−0.0040 (9)	0.0112 (9)
F6	0.0360 (11)	0.0318 (11)	0.0482 (14)	0.0061 (9)	0.0097 (10)	0.0225 (10)
O1	0.0189 (11)	0.0214 (11)	0.0216 (13)	0.0002 (8)	−0.0014 (9)	0.0033 (9)
N1	0.0161 (12)	0.0221 (13)	0.0230 (15)	0.0049 (10)	−0.0009 (10)	0.0016 (11)
N2	0.0162 (13)	0.0197 (13)	0.0201 (15)	0.0033 (10)	−0.0002 (10)	0.0017 (11)
C1	0.0158 (14)	0.0208 (15)	0.0208 (17)	0.0049 (11)	−0.0011 (12)	−0.0011 (13)
C2	0.0147 (14)	0.0213 (15)	0.0200 (17)	0.0024 (11)	0.0014 (11)	0.0027 (13)
C3	0.0202 (15)	0.0163 (14)	0.0193 (17)	0.0047 (11)	−0.0001 (12)	0.0017 (12)
C4	0.0139 (14)	0.0192 (15)	0.0195 (17)	0.0027 (11)	−0.0001 (11)	0.0002 (12)
C5	0.0183 (15)	0.0226 (16)	0.0259 (18)	0.0063 (12)	0.0009 (12)	0.0025 (14)
C6	0.0125 (14)	0.0267 (16)	0.0312 (19)	0.0030 (12)	0.0026 (12)	0.0043 (14)
C7	0.0192 (16)	0.0276 (17)	0.032 (2)	0.0017 (13)	0.0030 (13)	0.0078 (15)
C8	0.0211 (15)	0.0187 (15)	0.0241 (18)	0.0036 (12)	−0.0007 (12)	0.0021 (13)
C9	0.0189 (15)	0.0173 (14)	0.0216 (17)	0.0049 (11)	0.0002 (12)	0.0010 (12)
C10	0.0178 (15)	0.0251 (16)	0.0297 (19)	0.0058 (12)	−0.0008 (13)	0.0036 (14)
C11	0.0230 (16)	0.0239 (16)	0.031 (2)	0.0034 (13)	0.0022 (14)	0.0075 (15)
C12	0.0127 (14)	0.0198 (15)	0.0229 (17)	0.0040 (11)	0.0000 (11)	0.0047 (13)
C13	0.0156 (14)	0.0219 (15)	0.0165 (16)	0.0045 (11)	0.0022 (11)	0.0052 (12)
C14	0.0243 (16)	0.0326 (18)	0.0203 (18)	0.0088 (13)	−0.0045 (13)	0.0002 (14)
C15	0.0336 (19)	0.0365 (19)	0.0172 (18)	0.0116 (15)	−0.0039 (14)	0.0003 (15)
C16	0.0264 (17)	0.0268 (17)	0.0230 (19)	0.0041 (13)	0.0033 (13)	−0.0013 (14)
C17	0.0205 (15)	0.0176 (15)	0.0228 (18)	0.0039 (11)	0.0038 (12)	0.0045 (13)
F7	0.0547 (18)	0.0618 (19)	0.127 (3)	−0.0282 (14)	0.0462 (19)	−0.0129 (19)
F8	0.0204 (11)	0.098 (2)	0.0746 (19)	0.0233 (12)	0.0199 (11)	0.0562 (17)
F9	0.0271 (12)	0.144 (3)	0.0493 (17)	0.0202 (14)	0.0152 (11)	0.0595 (19)
F10	0.0382 (12)	0.0429 (12)	0.0272 (12)	0.0135 (9)	0.0061 (9)	0.0139 (10)
F11	0.0348 (12)	0.0283 (11)	0.0494 (14)	−0.0020 (9)	0.0005 (10)	0.0177 (10)
F12	0.0325 (11)	0.0342 (11)	0.0385 (13)	0.0146 (9)	−0.0008 (9)	0.0159 (10)
O2	0.0196 (11)	0.0317 (13)	0.0199 (13)	0.0086 (9)	−0.0029 (9)	0.0047 (10)
N3	0.0180 (13)	0.0271 (14)	0.0257 (16)	0.0047 (10)	0.0039 (11)	0.0090 (12)
N4	0.0184 (13)	0.0221 (13)	0.0167 (14)	0.0072 (10)	0.0028 (10)	0.0046 (11)
C18	0.0174 (15)	0.0301 (17)	0.0241 (18)	0.0027 (12)	0.0015 (12)	0.0058 (14)
C19	0.0144 (14)	0.0258 (16)	0.0272 (19)	0.0059 (12)	0.0034 (12)	0.0053 (14)
C20	0.0171 (14)	0.0190 (15)	0.0186 (17)	0.0019 (11)	−0.0005 (11)	0.0006 (12)
C21	0.0143 (14)	0.0207 (15)	0.0198 (17)	0.0015 (11)	−0.0004 (11)	0.0021 (13)
C22	0.0184 (15)	0.0215 (15)	0.0172 (16)	0.0033 (11)	0.0008 (11)	0.0034 (12)
C23	0.0138 (14)	0.0256 (16)	0.0281 (19)	0.0037 (12)	0.0014 (12)	0.0024 (14)
C24	0.0211 (15)	0.0201 (15)	0.0252 (18)	0.0057 (12)	−0.0020 (12)	0.0023 (13)
C25	0.0219 (15)	0.0207 (15)	0.0232 (18)	0.0026 (12)	−0.0024 (12)	0.0041 (13)
C26	0.0187 (15)	0.0184 (14)	0.0185 (17)	0.0024 (11)	−0.0009 (12)	0.0007 (12)
C27	0.0206 (17)	0.044 (2)	0.039 (2)	0.0029 (15)	0.0051 (15)	0.0150 (18)
C28	0.0248 (17)	0.0272 (17)	0.0271 (19)	0.0069 (13)	0.0003 (13)	0.0079 (15)
C29	0.0141 (14)	0.0211 (15)	0.0196 (17)	0.0051 (11)	0.0009 (11)	0.0030 (13)
C30	0.0179 (14)	0.0226 (15)	0.0160 (16)	0.0057 (11)	0.0026 (11)	0.0026 (12)
C31	0.0212 (16)	0.0232 (16)	0.0284 (19)	0.0010 (12)	−0.0007 (13)	0.0080 (14)
C32	0.0265 (17)	0.0225 (16)	0.036 (2)	0.0081 (13)	−0.0040 (14)	−0.0009 (15)
C33	0.040 (2)	0.0285 (18)	0.0228 (19)	0.0104 (15)	0.0041 (15)	−0.0023 (15)
C34	0.0284 (17)	0.0270 (17)	0.0219 (18)	0.0071 (13)	0.0099 (13)	0.0041 (14)
O3	0.0218 (11)	0.0347 (13)	0.0185 (13)	0.0113 (9)	0.0004 (9)	0.0046 (10)
O4	0.0181 (11)	0.0343 (13)	0.0224 (13)	0.0115 (9)	−0.0002 (9)	0.0033 (10)
O5	0.0206 (11)	0.0249 (11)	0.0186 (12)	0.0031 (9)	0.0006 (9)	0.0023 (9)
O6	0.0150 (10)	0.0225 (11)	0.0261 (13)	0.0024 (8)	0.0035 (9)	0.0027 (9)
C35	0.0149 (14)	0.0185 (15)	0.0261 (18)	0.0035 (11)	0.0024 (12)	0.0071 (13)
C36	0.0194 (15)	0.0266 (16)	0.0194 (17)	0.0082 (12)	0.0030 (12)	0.0056 (13)
C37	0.0146 (14)	0.0222 (15)	0.0193 (17)	0.0042 (11)	0.0012 (11)	0.0028 (13)
C38	0.0170 (14)	0.0190 (15)	0.0189 (17)	0.0068 (11)	0.0015 (11)	0.0061 (12)
O7	0.0374 (16)	0.111 (3)	0.0352 (18)	0.0244 (17)	0.0060 (13)	0.0237 (19)
C39	0.074 (4)	0.136 (6)	0.040 (3)	0.053 (4)	−0.015 (3)	−0.004 (3)
C40	0.052 (3)	0.220 (9)	0.058 (4)	0.060 (4)	0.004 (3)	0.036 (5)

Geometric parameters (Å, º) top

F1—C10	1.328 (4)	N4—C31	1.502 (4)
F2—C10	1.333 (4)	N4—C30	1.502 (4)
F3—C10	1.321 (4)	N4—H3N	0.882 (10)
F4—C11	1.338 (4)	N4—H4N	0.882 (10)
F5—C11	1.338 (4)	C18—C19	1.403 (5)
F6—C11	1.352 (4)	C18—C27	1.518 (5)
O1—C12	1.406 (4)	C19—C20	1.373 (4)
O1—H1O	0.840 (10)	C19—H19	0.9500
N1—C1	1.319 (4)	C20—C21	1.419 (4)
N1—C9	1.358 (4)	C20—C29	1.522 (4)
N2—C13	1.495 (4)	C21—C22	1.421 (4)
N2—C14	1.497 (4)	C21—C26	1.423 (4)
N2—H1N	0.880 (10)	C22—C23	1.366 (4)
N2—H2N	0.883 (10)	C22—H22	0.9500
C1—C2	1.401 (4)	C23—C24	1.404 (5)
C1—C10	1.517 (4)	C23—H23	0.9500
C2—C3	1.370 (4)	C24—C25	1.365 (5)
C2—H2	0.9500	C24—H24	0.9500
C3—C4	1.425 (4)	C25—C26	1.435 (4)
C3—C12	1.530 (4)	C25—C28	1.504 (5)
C4—C5	1.422 (4)	C29—C30	1.533 (4)
C4—C9	1.428 (4)	C29—H29	1.0000
C5—C6	1.357 (5)	C30—C34	1.519 (4)
C5—H5	0.9500	C30—H30	1.0000
C6—C7	1.406 (5)	C31—C32	1.504 (5)
C6—H6	0.9500	C31—H31A	0.9900
C7—C8	1.365 (4)	C31—H31B	0.9900
C7—H7	0.9500	C32—C33	1.532 (5)
C8—C9	1.427 (4)	C32—H32A	0.9900
C8—C11	1.503 (4)	C32—H32B	0.9900
C12—C13	1.533 (4)	C33—C34	1.529 (5)
C12—H12	1.0000	C33—H33A	0.9900
C13—C17	1.525 (4)	C33—H33B	0.9900
C13—H13	1.0000	C34—H34A	0.9900
C14—C15	1.519 (5)	C34—H34B	0.9900
C14—H14A	0.9900	O3—C35	1.236 (4)
C14—H14B	0.9900	O4—C35	1.285 (4)
C15—C16	1.529 (5)	O5—C38	1.255 (4)
C15—H15A	0.9900	O6—C38	1.271 (4)
C15—H15B	0.9900	C35—C36	1.522 (4)
C16—C17	1.527 (5)	C36—C37	1.517 (4)
C16—H16A	0.9900	C36—H36A	0.9900
C16—H16B	0.9900	C36—H36B	0.9900
C17—H17A	0.9900	C37—C38	1.517 (4)
C17—H17B	0.9900	C37—H37A	0.9900
F7—C27	1.323 (5)	C37—H37B	0.9900
F8—C27	1.331 (4)	O7—C39	1.347 (6)
F9—C27	1.304 (5)	O7—H7O	0.847 (10)
F10—C28	1.340 (4)	C39—C40	1.388 (8)
F11—C28	1.341 (4)	C39—H39A	0.9900
F12—C28	1.346 (4)	C39—H39B	0.9900
O2—C29	1.409 (3)	C40—H40A	0.9800
O2—H2O	0.841 (10)	C40—H40B	0.9800
N3—C18	1.309 (4)	C40—H40C	0.9800
N3—C26	1.363 (4)

C12—O1—H1O	104 (3)	C21—C20—C29	121.6 (3)
C1—N1—C9	116.7 (3)	C22—C21—C20	123.7 (3)
C13—N2—C14	113.4 (2)	C22—C21—C26	119.0 (3)
C13—N2—H1N	111 (2)	C20—C21—C26	117.3 (3)
C14—N2—H1N	106 (2)	C23—C22—C21	120.4 (3)
C13—N2—H2N	106 (2)	C23—C22—H22	119.8
C14—N2—H2N	112 (2)	C21—C22—H22	119.8
H1N—N2—H2N	108 (3)	C22—C23—C24	120.8 (3)
N1—C1—C2	125.4 (3)	C22—C23—H23	119.6
N1—C1—C10	114.3 (3)	C24—C23—H23	119.6
C2—C1—C10	120.2 (3)	C25—C24—C23	120.8 (3)
C3—C2—C1	118.6 (3)	C25—C24—H24	119.6
C3—C2—H2	120.7	C23—C24—H24	119.6
C1—C2—H2	120.7	C24—C25—C26	120.1 (3)
C2—C3—C4	118.9 (3)	C24—C25—C28	120.7 (3)
C2—C3—C12	119.8 (3)	C26—C25—C28	119.2 (3)
C4—C3—C12	121.3 (3)	N3—C26—C21	123.3 (3)
C5—C4—C3	124.0 (3)	N3—C26—C25	117.9 (3)
C5—C4—C9	118.7 (3)	C21—C26—C25	118.8 (3)
C3—C4—C9	117.3 (3)	F9—C27—F7	107.9 (3)
C6—C5—C4	120.8 (3)	F9—C27—F8	106.4 (3)
C6—C5—H5	119.6	F7—C27—F8	105.4 (3)
C4—C5—H5	119.6	F9—C27—C18	113.5 (3)
C5—C6—C7	120.7 (3)	F7—C27—C18	111.5 (3)
C5—C6—H6	119.7	F8—C27—C18	111.6 (3)
C7—C6—H6	119.7	F10—C28—F11	107.0 (3)
C8—C7—C6	120.8 (3)	F10—C28—F12	106.1 (3)
C8—C7—H7	119.6	F11—C28—F12	106.4 (3)
C6—C7—H7	119.6	F10—C28—C25	112.0 (3)
C7—C8—C9	120.1 (3)	F11—C28—C25	113.4 (3)
C7—C8—C11	120.1 (3)	F12—C28—C25	111.4 (3)
C9—C8—C11	119.7 (3)	O2—C29—C20	111.7 (2)
N1—C9—C8	118.1 (3)	O2—C29—C30	107.7 (2)
N1—C9—C4	123.0 (3)	C20—C29—C30	110.8 (3)
C8—C9—C4	118.8 (3)	O2—C29—H29	108.9
F3—C10—F1	107.1 (3)	C20—C29—H29	108.9
F3—C10—F2	106.5 (3)	C30—C29—H29	108.9
F1—C10—F2	105.9 (3)	N4—C30—C34	110.2 (2)
F3—C10—C1	113.2 (3)	N4—C30—C29	106.9 (2)
F1—C10—C1	111.1 (3)	C34—C30—C29	113.9 (3)
F2—C10—C1	112.5 (3)	N4—C30—H30	108.6
F5—C11—F4	107.0 (3)	C34—C30—H30	108.6
F5—C11—F6	106.0 (3)	C29—C30—H30	108.6
F4—C11—F6	106.2 (3)	N4—C31—C32	110.6 (3)
F5—C11—C8	114.0 (3)	N4—C31—H31A	109.5
F4—C11—C8	112.6 (3)	C32—C31—H31A	109.5
F6—C11—C8	110.6 (3)	N4—C31—H31B	109.5
O1—C12—C3	112.0 (2)	C32—C31—H31B	109.5
O1—C12—C13	107.7 (2)	H31A—C31—H31B	108.1
C3—C12—C13	112.0 (2)	C31—C32—C33	110.5 (3)
O1—C12—H12	108.4	C31—C32—H32A	109.5
C3—C12—H12	108.4	C33—C32—H32A	109.5
C13—C12—H12	108.4	C31—C32—H32B	109.5
N2—C13—C17	110.2 (2)	C33—C32—H32B	109.5
N2—C13—C12	107.1 (2)	H32A—C32—H32B	108.1
C17—C13—C12	113.9 (2)	C34—C33—C32	109.4 (3)
N2—C13—H13	108.5	C34—C33—H33A	109.8
C17—C13—H13	108.5	C32—C33—H33A	109.8
C12—C13—H13	108.5	C34—C33—H33B	109.8
N2—C14—C15	110.6 (3)	C32—C33—H33B	109.8
N2—C14—H14A	109.5	H33A—C33—H33B	108.2
C15—C14—H14A	109.5	C30—C34—C33	110.9 (3)
N2—C14—H14B	109.5	C30—C34—H34A	109.5
C15—C14—H14B	109.5	C33—C34—H34A	109.5
H14A—C14—H14B	108.1	C30—C34—H34B	109.5
C14—C15—C16	111.4 (3)	C33—C34—H34B	109.5
C14—C15—H15A	109.4	H34A—C34—H34B	108.0
C16—C15—H15A	109.4	O3—C35—O4	123.2 (3)
C14—C15—H15B	109.4	O3—C35—C36	121.1 (3)
C16—C15—H15B	109.4	O4—C35—C36	115.7 (3)
H15A—C15—H15B	108.0	C37—C36—C35	114.3 (3)
C17—C16—C15	110.5 (3)	C37—C36—H36A	108.7
C17—C16—H16A	109.5	C35—C36—H36A	108.7
C15—C16—H16A	109.5	C37—C36—H36B	108.7
C17—C16—H16B	109.5	C35—C36—H36B	108.7
C15—C16—H16B	109.5	H36A—C36—H36B	107.6
H16A—C16—H16B	108.1	C38—C37—C36	112.7 (3)
C13—C17—C16	110.9 (2)	C38—C37—H37A	109.1
C13—C17—H17A	109.5	C36—C37—H37A	109.1
C16—C17—H17A	109.5	C38—C37—H37B	109.1
C13—C17—H17B	109.5	C36—C37—H37B	109.1
C16—C17—H17B	109.5	H37A—C37—H37B	107.8
H17A—C17—H17B	108.1	O5—C38—O6	123.4 (3)
C29—O2—H2O	113 (3)	O5—C38—C37	118.3 (3)
C18—N3—C26	116.1 (3)	O6—C38—C37	118.3 (3)
C31—N4—C30	114.0 (2)	C39—O7—H7O	112 (4)
C31—N4—H3N	108 (2)	O7—C39—C40	122.4 (5)
C30—N4—H3N	111 (2)	O7—C39—H39A	106.7
C31—N4—H4N	111 (2)	C40—C39—H39A	106.7
C30—N4—H4N	105 (2)	O7—C39—H39B	106.7
H3N—N4—H4N	108 (3)	C40—C39—H39B	106.7
N3—C18—C19	126.2 (3)	H39A—C39—H39B	106.6
N3—C18—C27	113.7 (3)	C39—C40—H40A	109.5
C19—C18—C27	120.0 (3)	C39—C40—H40B	109.5
C20—C19—C18	118.0 (3)	H40A—C40—H40B	109.5
C20—C19—H19	121.0	C39—C40—H40C	109.5
C18—C19—H19	121.0	H40A—C40—H40C	109.5
C19—C20—C21	119.0 (3)	H40B—C40—H40C	109.5
C19—C20—C29	119.4 (3)

C9—N1—C1—C2	−2.4 (5)	C27—C18—C19—C20	−176.8 (3)
C9—N1—C1—C10	174.4 (3)	C18—C19—C20—C21	0.5 (5)
N1—C1—C2—C3	1.3 (5)	C18—C19—C20—C29	−179.9 (3)
C10—C1—C2—C3	−175.4 (3)	C19—C20—C21—C22	176.8 (3)
C1—C2—C3—C4	1.1 (4)	C29—C20—C21—C22	−2.9 (5)
C1—C2—C3—C12	−179.9 (3)	C19—C20—C21—C26	−2.2 (4)
C2—C3—C4—C5	176.1 (3)	C29—C20—C21—C26	178.1 (3)
C12—C3—C4—C5	−2.8 (5)	C20—C21—C22—C23	−179.1 (3)
C2—C3—C4—C9	−2.1 (4)	C26—C21—C22—C23	−0.2 (5)
C12—C3—C4—C9	178.9 (3)	C21—C22—C23—C24	−0.9 (5)
C3—C4—C5—C6	−178.4 (3)	C22—C23—C24—C25	0.1 (5)
C9—C4—C5—C6	−0.2 (5)	C23—C24—C25—C26	1.8 (5)
C4—C5—C6—C7	−0.4 (5)	C23—C24—C25—C28	−176.5 (3)
C5—C6—C7—C8	−0.1 (5)	C18—N3—C26—C21	−0.7 (5)
C6—C7—C8—C9	1.3 (5)	C18—N3—C26—C25	−179.2 (3)
C6—C7—C8—C11	−176.2 (3)	C22—C21—C26—N3	−176.6 (3)
C1—N1—C9—C8	−177.5 (3)	C20—C21—C26—N3	2.4 (5)
C1—N1—C9—C4	1.2 (5)	C22—C21—C26—C25	1.9 (4)
C7—C8—C9—N1	176.8 (3)	C20—C21—C26—C25	−179.0 (3)
C11—C8—C9—N1	−5.6 (5)	C24—C25—C26—N3	175.9 (3)
C7—C8—C9—C4	−2.0 (5)	C28—C25—C26—N3	−5.8 (4)
C11—C8—C9—C4	175.6 (3)	C24—C25—C26—C21	−2.7 (5)
C5—C4—C9—N1	−177.3 (3)	C28—C25—C26—C21	175.5 (3)
C3—C4—C9—N1	1.0 (5)	N3—C18—C27—F9	47.0 (5)
C5—C4—C9—C8	1.4 (4)	C19—C18—C27—F9	−134.4 (4)
C3—C4—C9—C8	179.7 (3)	N3—C18—C27—F7	−75.0 (4)
N1—C1—C10—F3	42.1 (4)	C19—C18—C27—F7	103.5 (4)
C2—C1—C10—F3	−140.9 (3)	N3—C18—C27—F8	167.3 (3)
N1—C1—C10—F1	−78.4 (4)	C19—C18—C27—F8	−14.2 (5)
C2—C1—C10—F1	98.6 (4)	C24—C25—C28—F10	118.1 (3)
N1—C1—C10—F2	163.0 (3)	C26—C25—C28—F10	−60.2 (4)
C2—C1—C10—F2	−20.0 (4)	C24—C25—C28—F11	−120.7 (3)
C7—C8—C11—F5	−121.8 (3)	C26—C25—C28—F11	61.1 (4)
C9—C8—C11—F5	60.6 (4)	C24—C25—C28—F12	−0.6 (4)
C7—C8—C11—F4	116.1 (3)	C26—C25—C28—F12	−178.9 (3)
C9—C8—C11—F4	−61.5 (4)	C19—C20—C29—O2	−14.1 (4)
C7—C8—C11—F6	−2.5 (5)	C21—C20—C29—O2	165.5 (3)
C9—C8—C11—F6	179.9 (3)	C19—C20—C29—C30	105.9 (3)
C2—C3—C12—O1	−15.4 (4)	C21—C20—C29—C30	−74.4 (4)
C4—C3—C12—O1	163.5 (3)	C31—N4—C30—C34	53.7 (3)
C2—C3—C12—C13	105.7 (3)	C31—N4—C30—C29	177.9 (2)
C4—C3—C12—C13	−75.4 (4)	O2—C29—C30—N4	−68.4 (3)
C14—N2—C13—C17	56.2 (3)	C20—C29—C30—N4	169.2 (2)
C14—N2—C13—C12	−179.4 (2)	O2—C29—C30—C34	53.6 (3)
O1—C12—C13—N2	−63.4 (3)	C20—C29—C30—C34	−68.9 (3)
C3—C12—C13—N2	173.1 (2)	C30—N4—C31—C32	−54.6 (3)
O1—C12—C13—C17	58.7 (3)	N4—C31—C32—C33	56.3 (4)
C3—C12—C13—C17	−64.8 (3)	C31—C32—C33—C34	−58.7 (4)
C13—N2—C14—C15	−55.5 (4)	N4—C30—C34—C33	−55.2 (4)
N2—C14—C15—C16	54.4 (4)	C29—C30—C34—C33	−175.3 (3)
C14—C15—C16—C17	−55.4 (4)	C32—C33—C34—C30	58.3 (4)
N2—C13—C17—C16	−55.8 (3)	O3—C35—C36—C37	−3.0 (4)
C12—C13—C17—C16	−176.1 (3)	O4—C35—C36—C37	177.4 (3)
C15—C16—C17—C13	56.0 (3)	C35—C36—C37—C38	175.4 (3)
C26—N3—C18—C19	−1.4 (5)	C36—C37—C38—O5	55.5 (4)
C26—N3—C18—C27	177.0 (3)	C36—C37—C38—O6	−124.1 (3)
N3—C18—C19—C20	1.5 (5)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the (N1,C1–C4,C9) ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N···O1	0.88 (3)	2.49 (3)	2.806 (4)	102 (2)
N4—H3N···O2	0.88 (2)	2.54 (3)	2.863 (4)	103 (2)
O1—H1O···O6	0.84 (3)	1.81 (3)	2.653 (3)	175 (2)
O2—H2O···O4ⁱ	0.84 (2)	1.82 (2)	2.656 (3)	170 (3)
N2—H1N···O5ⁱⁱ	0.88 (3)	1.97 (3)	2.830 (4)	165 (3)
N2—H2N···O4ⁱ	0.88 (3)	1.82 (3)	2.694 (4)	173 (3)
N4—H3N···O3ⁱⁱ	0.88 (2)	1.99 (3)	2.832 (4)	161 (3)
N4—H4N···O6	0.89 (3)	1.92 (3)	2.789 (4)	168 (3)
O7—H7O···O5	0.85 (3)	1.88 (3)	2.729 (4)	176 (7)
C30—H30···O7	1.00	2.40	3.296 (4)	149
C10—F3···Cg1ⁱⁱⁱ	1.32 (1)	3.28 (1)	4.101 (3)	120 (1)

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

Summary of short interatomic contacts (Å) in (I)^a top

Contact	Distance	Symmetry operation
F1···H6	2.50	1 + x, y, z
F6···C32	3.096 (4)	x, -1 + y, z
O1···H37B	2.45	x, y, z
O1···C38	3.038 (4)	-x, -y, -1 - z
O2···H36B	2.50	-1 + x, y, z
O2···C36	3.090 (4)	-1 + x, y, z
O4···H12	2.53	1 + x, y, z
O6···H22	2.50	x, y, z
O7···H31B	2.55	x, y, z
H1O···H37B	2.14	x, y, z
H12···H29	2.06	x, y, z
H34A···H39A	2.22	-x, 2 - y, -z

Notes: (a) The interatomic distances are calculated in Crystal Explorer (Turner et al., 2017) whereby the X—H bond lengths are adjusted to their neutron values.

Percentage contributions of interatomic contacts to the Hirshfeld surface for (I) top

Contact	Percentage contribution
H···H	29.8
O···H/H···O	14.0
F···H/H···F	41.2
F···F	5.7
C···H/H···C	4.1
C···F/F···C	2.8
N···H/H···N	1.0
C···N/N···C	0.5
C···O/O···C	0.3
O···O	0.2
F···N/N···F	0.2
C···C	0.2
F···O/O···F	0.1

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

Bis(mefloquinium) butane­dioate ethanol monosolvate: crystal structure and Hirshfeld surface analysis

Supporting information

Key indicators

checkCIF/PLATON results

Bis(mefloquinium) butanedioate ethanol monosolvate: crystal structure and Hirshfeld surface analysis