Hydrogen-bonding patterns in 2,2-bis­(4-methyl­phen­yl)hexa­fluoro­propane pyridinium and ethyl­enedi­ammonium salt crystals

Sugiyama, H.

doi:10.1107/S2056989020005575

Hydrogen-bonding patterns in 2,2-bis(4-methylphenyl)hexafluoropropane pyridinium and ethylenediammonium salt crystals

The crystal structures of two salt crystals of 2,2-bis(4-methylphenyl)hexafluoropropane (Bmphfp) with amines, namely, dipyridinium 4,4′-(1,1,1,3,3,3-hexafluoropropane-2,2-diyl)dibenzoate 4,4′-(1,1,1,3,3,3-hexafluoropropane-2,2-diyl)dibenzoic acid (1) and a monohydrated ethylenediammonium salt ethane-1,2-diaminium 4,4′-(1,1,1,3,3,3-hexafluoropropane-2,2-diyl)dibenzoate monohydrate (2) are reported.

Keywords: crystal structure; organic salt; hydrogen-bonding networks.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989020005575/lh5959sup1.cif Contains datablocks 1, 2, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989020005575/lh59591sup2.hkl Contains datablock 1
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989020005575/lh59592sup3.hkl Contains datablock 2

CCDC references: 1998170; 1998169

checkCIF report

Key indicators

Structure: 1

Single-crystal X-ray study
T = 93 K
Mean (C-C) = 0.002 Å
R factor = 0.033
wR factor = 0.087
Data-to-parameter ratio = 13.7

Structure: 2

Single-crystal X-ray study
T = 93 K
Mean (C-C) = 0.002 Å
R factor = 0.032
wR factor = 0.082
Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Datablock: 1


Alert level A
ABSMU01_ALERT_1_A  The ratio of given/expected absorption coefficient lies
               outside the range 0.90 <> 1.10
            Calculated value of mu =     0.625
            Value of mu given      =     1.251
DENSD01_ALERT_1_A  The ratio of the submitted crystal density and that
            calculated from the formula is outside the range 0.90 <> 1.10
            Crystal density given    =      1.538
            Calculated crystal density =      0.769
PLAT043_ALERT_1_A Calculated and Reported Mol. Weight Differ by ..     471.35 Check
PLAT046_ALERT_1_A Reported Z, MW and D(calc) are Inconsistent ....      0.769 Check

Alert level C
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT041_ALERT_1_C Calc. and Reported SumFormula    Strings  Differ     Please Check
PLAT097_ALERT_2_C Large Reported Max.  (Positive) Residual Density       0.71 eA-3
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          4 Report
PLAT976_ALERT_2_C Check Calcd Resid. Dens.  0.90A   From O26            -0.54 eA-3

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:   C22 H15 F6 N1 O4
            Atom count from _chemical_formula_moiety:C44 H30 F12 N2 O8
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C22 H15 F6 N1 O4
            Atom count from the _atom_site data:  C44 H30 F12 N2 O8
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G ALERT: Large difference may be due to a
            symmetry error - see SYMMG tests
           From the CIF: _cell_formula_units_Z    4
           From the CIF: _chemical_formula_sum  C22 H15 F6 N O4
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         88.00    176.00  -88.00
           H         60.00    120.00  -60.00
           F         24.00     48.00  -24.00
           N          4.00      8.00   -4.00
           O         16.00     32.00  -16.00
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          4 Report
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact F13      ..F44              2.70 Ang.
                                                1-x,2-y,1-z  =      3_676 Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact F18      ..F41              2.83 Ang.
                                                1-x,1-y,1-z  =      3_666 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        350 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         19 Info

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

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




Datablock: 2


Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          8 Report
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        176 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         19 Info

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

   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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Computing details top

For both structures, data collection: CrysAlis PRO (Rigaku OD, 2019); cell refinement: CrysAlis PRO (Rigaku OD, 2019); data reduction: CrysAlis PRO (Rigaku OD, 2019); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Dipyridinium 4,4'-(1,1,1,3,3,3-hexafluoropropane-2,2-diyl)dibenzoate 4,4'-(1,1,1,3,3,3-hexafluoropropane-2,2-diyl)dibenzoic acid (1) top

Crystal data top

2C₅H₆N⁺·C₁₇H₈F₆O₄²⁻·C₁₇H₁₀F₆O₄	F(000) = 1920
M_r = 471.35	D_x = 1.538 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 25.5453 (7) Å	Cell parameters from 18343 reflections
b = 13.4125 (4) Å	θ = 3.4–76.1°
c = 11.8879 (4) Å	µ = 1.25 mm⁻¹
β = 91.644 (3)°	T = 93 K
V = 4071.4 (2) Å³	Plate, colourless
Z = 4	0.3 × 0.25 × 0.05 mm

Data collection top

XtaLAB Synergy R, DW system, HyPix diffractometer	8170 independent reflections
Radiation source: Rotating-anode X-ray tube, Rigaku (Cu) X-ray Source	7361 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.031
Detector resolution: 10.0000 pixels mm^-1	θ_max = 76.3°, θ_min = 3.5°
ω scans	h = −30→32
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2019)	k = −16→13
T_min = 0.743, T_max = 0.940	l = −13→14
30654 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.087	w = 1/[σ²(F_o²) + (0.0395P)² + 1.9293P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
8170 reflections	Δρ_max = 0.71 e Å⁻³
597 parameters	Δρ_min = −0.47 e Å⁻³
0 restraints

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.

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

	x	y	z	U_iso*/U_eq
F12	0.22833 (3)	1.08247 (6)	0.68130 (7)	0.02200 (17)
F17	0.22585 (3)	0.91369 (6)	0.96846 (6)	0.02322 (17)
F40	0.70683 (3)	0.41820 (6)	0.27299 (7)	0.02356 (17)
F44	0.76965 (3)	0.72779 (6)	0.13841 (7)	0.02456 (18)
F13	0.26623 (3)	1.08382 (6)	0.84616 (7)	0.02303 (17)
F16	0.30597 (3)	0.91053 (6)	0.91890 (7)	0.02226 (17)
F18	0.25655 (3)	0.78308 (6)	0.88772 (7)	0.02241 (17)
F41	0.74214 (3)	0.42826 (6)	0.11122 (7)	0.02445 (18)
F46	0.79621 (3)	0.58962 (6)	0.06906 (7)	0.02426 (18)
F42	0.18370 (3)	1.05339 (6)	0.82787 (7)	0.02393 (18)
F45	0.71737 (3)	0.63923 (7)	0.03330 (7)	0.02663 (19)
F39	0.66577 (3)	0.49010 (6)	0.13508 (7)	0.02771 (19)
O30	0.56288 (4)	0.74265 (8)	0.56887 (8)	0.0231 (2)
O3	0.02557 (4)	0.69282 (7)	0.63890 (8)	0.0213 (2)
H3	−0.001290	0.669702	0.605883	0.032*
O1	0.03424 (4)	0.77646 (7)	0.47641 (8)	0.0240 (2)
O27	0.45867 (4)	0.89389 (8)	0.49908 (9)	0.0266 (2)
H27	0.486853	0.870972	0.475153	0.040*
O53	0.93843 (4)	0.45833 (8)	0.54257 (9)	0.0265 (2)
O28	0.54442 (4)	0.84034 (8)	0.42017 (9)	0.0252 (2)
O55	0.93586 (4)	0.62306 (8)	0.57396 (9)	0.0272 (2)
N56	0.52505 (5)	0.87381 (9)	0.71195 (10)	0.0224 (2)
H56	0.533196	0.823332	0.668526	0.027*
N62	1.00463 (5)	0.43556 (9)	0.70485 (10)	0.0232 (2)
H62	0.982590	0.444347	0.647461	0.028*
O26	0.43599 (5)	0.73301 (10)	0.50208 (16)	0.0605 (5)
C47	0.78662 (5)	0.56715 (10)	0.29798 (11)	0.0162 (2)
C31	0.61372 (5)	0.72459 (10)	0.40592 (11)	0.0163 (2)
C7	0.19098 (5)	0.87600 (9)	0.72089 (11)	0.0163 (2)
C52	0.80108 (5)	0.64725 (10)	0.36757 (11)	0.0186 (3)
H52	0.780770	0.706591	0.365868	0.022*
C32	0.62560 (5)	0.75871 (10)	0.29904 (11)	0.0169 (2)
H32	0.606557	0.813212	0.267331	0.020*
C19	0.28904 (5)	0.90407 (10)	0.69532 (11)	0.0162 (2)
C29	0.57024 (5)	0.77278 (10)	0.47017 (11)	0.0180 (3)
C36	0.64238 (5)	0.64523 (10)	0.45168 (11)	0.0182 (3)
H36	0.634564	0.620820	0.524315	0.022*
C33	0.66487 (5)	0.71425 (9)	0.23808 (11)	0.0168 (2)
H33	0.671986	0.737681	0.164671	0.020*
C4	0.09858 (5)	0.79697 (9)	0.62440 (11)	0.0173 (3)
C35	0.68223 (5)	0.60161 (10)	0.39192 (11)	0.0178 (3)
H35	0.701822	0.548206	0.424533	0.021*
C34	0.69390 (5)	0.63546 (9)	0.28405 (11)	0.0157 (2)
C50	0.87447 (5)	0.55365 (10)	0.44332 (11)	0.0181 (3)
C48	0.81786 (5)	0.48191 (10)	0.29880 (11)	0.0184 (3)
H48	0.809559	0.428344	0.249142	0.022*
C49	0.86115 (5)	0.47505 (10)	0.37207 (11)	0.0186 (3)
H49	0.881768	0.416092	0.373382	0.022*
C8	0.15374 (5)	0.83113 (10)	0.78814 (11)	0.0188 (3)
H8	0.159499	0.828271	0.867374	0.023*
C51	0.84482 (5)	0.64073 (10)	0.43901 (11)	0.0191 (3)
H51	0.854579	0.695867	0.485179	0.023*
C2	0.04955 (5)	0.75471 (10)	0.57097 (11)	0.0186 (3)
C24	0.32764 (5)	0.97498 (10)	0.67589 (11)	0.0185 (3)
H24	0.323435	1.041261	0.702336	0.022*
C37	0.73718 (5)	0.57962 (9)	0.22137 (11)	0.0163 (2)
C11	0.22998 (5)	1.03694 (10)	0.78160 (11)	0.0185 (3)
C9	0.10838 (5)	0.79069 (10)	0.74009 (11)	0.0195 (3)
H9	0.083840	0.758493	0.786396	0.023*
C5	0.13488 (5)	0.84415 (10)	0.55735 (11)	0.0192 (3)
H5	0.128171	0.850060	0.478619	0.023*
C22	0.37889 (5)	0.85221 (11)	0.58076 (11)	0.0200 (3)
C20	0.29548 (5)	0.80725 (10)	0.65561 (11)	0.0196 (3)
H20	0.269000	0.758830	0.666859	0.023*
C6	0.18083 (5)	0.88259 (10)	0.60500 (11)	0.0185 (3)
H6	0.205628	0.913677	0.558374	0.022*
C38	0.71313 (5)	0.47819 (10)	0.18464 (11)	0.0196 (3)
C54	0.92002 (5)	0.54511 (11)	0.52634 (11)	0.0203 (3)
C15	0.25742 (5)	0.88267 (10)	0.88711 (11)	0.0182 (3)
C10	0.24143 (5)	0.92433 (9)	0.76917 (11)	0.0162 (3)
C23	0.37220 (5)	0.94944 (10)	0.61817 (11)	0.0196 (3)
H23	0.398102	0.998398	0.604258	0.023*
C67	1.03435 (5)	0.35341 (11)	0.70980 (12)	0.0231 (3)
H67	1.031301	0.305248	0.651379	0.028*
C21	0.34043 (5)	0.78123 (10)	0.59972 (12)	0.0219 (3)
H21	0.344950	0.714718	0.574307	0.026*
C43	0.75479 (5)	0.63450 (10)	0.11453 (11)	0.0198 (3)
C66	1.06937 (6)	0.33770 (11)	0.79865 (13)	0.0258 (3)
H66	1.090530	0.279470	0.801645	0.031*
C25	0.42714 (5)	0.82031 (12)	0.52194 (13)	0.0256 (3)
C63	1.00803 (6)	0.50452 (11)	0.78613 (13)	0.0273 (3)
H63	0.986587	0.562295	0.780960	0.033*
C61	0.48846 (6)	0.86140 (12)	0.78893 (13)	0.0280 (3)
H61	0.472128	0.798293	0.797199	0.034*
C64	1.04211 (6)	0.49309 (12)	0.87715 (13)	0.0304 (3)
H64	1.044335	0.542326	0.934540	0.036*
C65	1.07304 (6)	0.40845 (12)	0.88328 (13)	0.0293 (3)
H65	1.096734	0.398921	0.945407	0.035*
C57	0.54946 (6)	0.96054 (12)	0.69936 (13)	0.0304 (3)
H57	0.575278	0.967025	0.643885	0.037*
C60	0.47446 (7)	0.93988 (13)	0.85612 (13)	0.0329 (3)
H60	0.448073	0.931561	0.910053	0.040*
C58	0.53768 (8)	1.04085 (13)	0.76581 (15)	0.0389 (4)
H58	0.555733	1.102259	0.757872	0.047*
C59	0.49903 (8)	1.03092 (13)	0.84465 (14)	0.0364 (4)
H59	0.489588	1.085949	0.890117	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F12	0.0255 (4)	0.0189 (4)	0.0218 (4)	0.0027 (3)	0.0038 (3)	0.0041 (3)
F17	0.0252 (4)	0.0302 (4)	0.0145 (4)	−0.0009 (3)	0.0046 (3)	−0.0028 (3)
F40	0.0271 (4)	0.0181 (4)	0.0257 (4)	−0.0030 (3)	0.0037 (3)	0.0010 (3)
F44	0.0301 (4)	0.0181 (4)	0.0260 (4)	0.0018 (3)	0.0096 (3)	0.0043 (3)
F13	0.0257 (4)	0.0185 (4)	0.0248 (4)	−0.0017 (3)	0.0006 (3)	−0.0058 (3)
F16	0.0203 (4)	0.0265 (4)	0.0198 (4)	−0.0028 (3)	−0.0032 (3)	−0.0002 (3)
F18	0.0281 (4)	0.0180 (4)	0.0209 (4)	−0.0010 (3)	−0.0014 (3)	0.0033 (3)
F41	0.0296 (4)	0.0221 (4)	0.0217 (4)	0.0034 (3)	0.0029 (3)	−0.0077 (3)
F46	0.0263 (4)	0.0267 (4)	0.0202 (4)	0.0080 (3)	0.0086 (3)	0.0014 (3)
F42	0.0221 (4)	0.0233 (4)	0.0268 (4)	0.0039 (3)	0.0093 (3)	−0.0032 (3)
F45	0.0300 (4)	0.0357 (5)	0.0142 (4)	0.0099 (4)	0.0002 (3)	0.0025 (3)
F39	0.0230 (4)	0.0292 (4)	0.0304 (4)	0.0022 (3)	−0.0078 (3)	−0.0085 (4)
O30	0.0224 (5)	0.0302 (5)	0.0168 (4)	0.0038 (4)	0.0035 (4)	−0.0002 (4)
O3	0.0169 (4)	0.0253 (5)	0.0218 (5)	−0.0046 (4)	0.0000 (4)	−0.0002 (4)
O1	0.0236 (5)	0.0272 (5)	0.0210 (5)	−0.0019 (4)	−0.0041 (4)	0.0005 (4)
O27	0.0184 (5)	0.0335 (5)	0.0284 (5)	0.0060 (4)	0.0092 (4)	0.0061 (4)
O53	0.0246 (5)	0.0287 (5)	0.0259 (5)	0.0059 (4)	−0.0046 (4)	−0.0005 (4)
O28	0.0198 (5)	0.0287 (5)	0.0274 (5)	0.0070 (4)	0.0082 (4)	0.0064 (4)
O55	0.0189 (5)	0.0302 (5)	0.0323 (6)	−0.0024 (4)	−0.0031 (4)	−0.0054 (4)
N56	0.0218 (6)	0.0274 (6)	0.0181 (5)	0.0059 (5)	0.0011 (4)	0.0010 (5)
N62	0.0187 (5)	0.0299 (6)	0.0209 (6)	−0.0022 (5)	0.0000 (4)	0.0053 (5)
O26	0.0351 (7)	0.0400 (7)	0.1084 (13)	−0.0065 (6)	0.0369 (8)	−0.0330 (8)
C47	0.0155 (6)	0.0186 (6)	0.0148 (6)	0.0005 (5)	0.0030 (5)	0.0019 (5)
C31	0.0133 (6)	0.0196 (6)	0.0161 (6)	−0.0017 (5)	0.0002 (5)	−0.0034 (5)
C7	0.0160 (6)	0.0161 (6)	0.0169 (6)	0.0015 (5)	0.0018 (5)	−0.0006 (5)
C52	0.0186 (6)	0.0166 (6)	0.0207 (6)	0.0020 (5)	0.0031 (5)	−0.0001 (5)
C32	0.0157 (6)	0.0171 (6)	0.0179 (6)	0.0002 (5)	−0.0010 (5)	0.0006 (5)
C19	0.0151 (6)	0.0194 (6)	0.0142 (6)	0.0014 (5)	0.0007 (5)	−0.0001 (5)
C29	0.0140 (6)	0.0209 (6)	0.0190 (6)	−0.0018 (5)	0.0005 (5)	−0.0017 (5)
C36	0.0179 (6)	0.0221 (6)	0.0146 (6)	−0.0009 (5)	0.0010 (5)	0.0003 (5)
C33	0.0178 (6)	0.0181 (6)	0.0147 (6)	−0.0003 (5)	0.0005 (5)	0.0007 (5)
C4	0.0161 (6)	0.0171 (6)	0.0189 (6)	0.0018 (5)	0.0019 (5)	−0.0014 (5)
C35	0.0193 (6)	0.0178 (6)	0.0164 (6)	0.0023 (5)	−0.0005 (5)	0.0006 (5)
C34	0.0153 (6)	0.0173 (6)	0.0145 (6)	−0.0001 (5)	0.0011 (5)	−0.0023 (5)
C50	0.0148 (6)	0.0219 (6)	0.0177 (6)	−0.0010 (5)	0.0036 (5)	0.0021 (5)
C48	0.0195 (6)	0.0178 (6)	0.0181 (6)	0.0006 (5)	0.0032 (5)	−0.0014 (5)
C49	0.0174 (6)	0.0188 (6)	0.0199 (6)	0.0029 (5)	0.0034 (5)	0.0015 (5)
C8	0.0195 (6)	0.0229 (6)	0.0142 (6)	−0.0009 (5)	0.0024 (5)	0.0000 (5)
C51	0.0188 (6)	0.0194 (6)	0.0194 (6)	−0.0022 (5)	0.0027 (5)	−0.0028 (5)
C2	0.0173 (6)	0.0177 (6)	0.0208 (6)	0.0019 (5)	0.0018 (5)	−0.0025 (5)
C24	0.0186 (6)	0.0174 (6)	0.0197 (6)	−0.0007 (5)	0.0016 (5)	0.0001 (5)
C37	0.0186 (6)	0.0158 (6)	0.0145 (6)	0.0023 (5)	0.0011 (5)	−0.0002 (5)
C11	0.0182 (6)	0.0188 (6)	0.0188 (6)	0.0003 (5)	0.0032 (5)	−0.0005 (5)
C9	0.0186 (6)	0.0212 (6)	0.0191 (6)	−0.0016 (5)	0.0043 (5)	0.0003 (5)
C5	0.0198 (6)	0.0225 (6)	0.0153 (6)	0.0010 (5)	0.0009 (5)	0.0007 (5)
C22	0.0156 (6)	0.0275 (7)	0.0169 (6)	0.0021 (5)	0.0000 (5)	−0.0023 (5)
C20	0.0173 (6)	0.0201 (6)	0.0213 (6)	−0.0016 (5)	0.0010 (5)	−0.0024 (5)
C6	0.0179 (6)	0.0211 (6)	0.0167 (6)	−0.0004 (5)	0.0035 (5)	0.0014 (5)
C38	0.0207 (6)	0.0198 (6)	0.0182 (6)	0.0024 (5)	−0.0001 (5)	−0.0024 (5)
C54	0.0146 (6)	0.0271 (7)	0.0194 (6)	−0.0009 (5)	0.0031 (5)	−0.0005 (5)
C15	0.0185 (6)	0.0192 (6)	0.0170 (6)	−0.0013 (5)	0.0015 (5)	−0.0020 (5)
C10	0.0174 (6)	0.0165 (6)	0.0150 (6)	−0.0007 (5)	0.0030 (5)	−0.0005 (5)
C23	0.0164 (6)	0.0236 (7)	0.0188 (6)	−0.0009 (5)	0.0008 (5)	0.0019 (5)
C67	0.0219 (7)	0.0254 (7)	0.0220 (7)	−0.0049 (5)	0.0026 (5)	0.0012 (6)
C21	0.0191 (6)	0.0220 (7)	0.0244 (7)	0.0021 (5)	0.0012 (5)	−0.0062 (5)
C43	0.0222 (6)	0.0202 (6)	0.0173 (6)	0.0054 (5)	0.0040 (5)	0.0001 (5)
C66	0.0215 (7)	0.0289 (7)	0.0268 (7)	−0.0002 (6)	0.0006 (6)	0.0067 (6)
C25	0.0179 (6)	0.0338 (8)	0.0254 (7)	0.0005 (6)	0.0035 (5)	−0.0073 (6)
C63	0.0273 (7)	0.0259 (7)	0.0291 (8)	0.0005 (6)	0.0076 (6)	0.0034 (6)
C61	0.0260 (7)	0.0338 (8)	0.0244 (7)	−0.0001 (6)	0.0040 (6)	0.0019 (6)
C64	0.0341 (8)	0.0328 (8)	0.0246 (7)	−0.0089 (6)	0.0041 (6)	−0.0037 (6)
C65	0.0244 (7)	0.0414 (9)	0.0218 (7)	−0.0064 (6)	−0.0029 (6)	0.0057 (6)
C57	0.0332 (8)	0.0311 (8)	0.0273 (8)	0.0009 (6)	0.0065 (6)	0.0064 (6)
C60	0.0348 (8)	0.0408 (9)	0.0237 (8)	0.0076 (7)	0.0089 (6)	0.0014 (7)
C58	0.0568 (11)	0.0266 (8)	0.0334 (9)	−0.0012 (7)	0.0069 (8)	0.0043 (7)
C59	0.0542 (11)	0.0309 (8)	0.0242 (8)	0.0140 (7)	0.0034 (7)	0.0005 (6)

Geometric parameters (Å, º) top

F12—C11	1.3392 (16)	C4—C9	1.3934 (19)
F17—C15	1.3429 (15)	C4—C5	1.3923 (19)
F40—C38	1.3365 (16)	C35—H35	0.9500
F44—C43	1.3357 (16)	C35—C34	1.4005 (18)
F13—C11	1.3419 (15)	C34—C37	1.5446 (17)
F16—C15	1.3392 (15)	C50—C49	1.3886 (19)
F18—C15	1.3359 (15)	C50—C51	1.3922 (19)
F41—C38	1.3404 (16)	C50—C54	1.5085 (18)
F46—C43	1.3441 (15)	C48—H48	0.9500
F42—C11	1.3367 (15)	C48—C49	1.3909 (19)
F45—C43	1.3407 (16)	C49—H49	0.9500
F39—C38	1.3399 (15)	C8—H8	0.9500
O30—C29	1.2602 (17)	C8—C9	1.3873 (19)
O3—H3	0.8400	C51—H51	0.9500
O3—C2	1.3209 (17)	C24—H24	0.9500
O1—C2	1.2152 (17)	C24—C23	1.3889 (19)
O27—H27	0.8400	C37—C38	1.5502 (18)
O27—C25	1.3073 (18)	C37—C43	1.5460 (18)
O53—C54	1.2680 (18)	C11—C10	1.5463 (18)
O28—C29	1.2596 (17)	C9—H9	0.9500
O55—C54	1.2507 (18)	C5—H5	0.9500
N56—H56	0.8800	C5—C6	1.3880 (19)
N56—C61	1.3371 (19)	C22—C23	1.390 (2)
N56—C57	1.330 (2)	C22—C21	1.391 (2)
N62—H62	0.8800	C22—C25	1.4968 (19)
N62—C67	1.3383 (19)	C20—H20	0.9500
N62—C63	1.339 (2)	C20—C21	1.3875 (19)
O26—C25	1.217 (2)	C6—H6	0.9500
C47—C52	1.3991 (18)	C15—C10	1.5532 (18)
C47—C48	1.3941 (18)	C23—H23	0.9500
C47—C37	1.5448 (17)	C67—H67	0.9500
C31—C32	1.3920 (18)	C67—C66	1.381 (2)
C31—C29	1.5113 (18)	C21—H21	0.9500
C31—C36	1.3935 (19)	C66—H66	0.9500
C7—C8	1.3965 (18)	C66—C65	1.384 (2)
C7—C6	1.3973 (18)	C63—H63	0.9500
C7—C10	1.5387 (17)	C63—C64	1.378 (2)
C52—H52	0.9500	C61—H61	0.9500
C52—C51	1.3865 (19)	C61—C60	1.375 (2)
C32—H32	0.9500	C64—H64	0.9500
C32—C33	1.3889 (18)	C64—C65	1.384 (2)
C19—C24	1.3941 (18)	C65—H65	0.9500
C19—C20	1.3931 (19)	C57—H57	0.9500
C19—C10	1.5443 (17)	C57—C58	1.374 (2)
C36—H36	0.9500	C60—H60	0.9500
C36—C35	1.3875 (18)	C60—C59	1.381 (3)
C33—H33	0.9500	C58—H58	0.9500
C33—C34	1.3936 (18)	C58—C59	1.387 (3)
C4—C2	1.4991 (18)	C59—H59	0.9500

C2—O3—H3	109.5	C8—C9—H9	119.8
C25—O27—H27	109.5	C4—C5—H5	119.8
C61—N56—H56	119.2	C6—C5—C4	120.31 (12)
C57—N56—H56	119.2	C6—C5—H5	119.8
C57—N56—C61	121.67 (13)	C23—C22—C21	119.76 (12)
C67—N62—H62	119.6	C23—C22—C25	121.87 (13)
C67—N62—C63	120.81 (13)	C21—C22—C25	118.35 (13)
C63—N62—H62	119.6	C19—C20—H20	119.9
C52—C47—C37	117.58 (11)	C21—C20—C19	120.27 (12)
C48—C47—C52	118.96 (12)	C21—C20—H20	119.9
C48—C47—C37	123.44 (11)	C7—C6—H6	119.7
C32—C31—C29	120.22 (12)	C5—C6—C7	120.65 (12)
C32—C31—C36	118.80 (12)	C5—C6—H6	119.7
C36—C31—C29	120.99 (12)	F40—C38—F41	106.99 (10)
C8—C7—C6	118.78 (12)	F40—C38—F39	106.84 (11)
C8—C7—C10	123.03 (11)	F40—C38—C37	111.26 (10)
C6—C7—C10	118.09 (11)	F41—C38—C37	113.57 (11)
C47—C52—H52	119.7	F39—C38—F41	106.39 (10)
C51—C52—C47	120.54 (12)	F39—C38—C37	111.39 (10)
C51—C52—H52	119.7	O53—C54—C50	116.42 (12)
C31—C32—H32	119.5	O55—C54—O53	125.79 (12)
C33—C32—C31	120.97 (12)	O55—C54—C50	117.79 (12)
C33—C32—H32	119.5	F17—C15—C10	113.00 (11)
C24—C19—C10	123.12 (11)	F16—C15—F17	106.31 (10)
C20—C19—C24	119.26 (12)	F16—C15—C10	111.83 (11)
C20—C19—C10	117.34 (11)	F18—C15—F17	107.19 (11)
O30—C29—C31	117.70 (12)	F18—C15—F16	107.03 (10)
O28—C29—O30	125.45 (12)	F18—C15—C10	111.14 (10)
O28—C29—C31	116.85 (12)	C7—C10—C19	112.24 (10)
C31—C36—H36	119.8	C7—C10—C11	106.77 (10)
C35—C36—C31	120.47 (12)	C7—C10—C15	112.39 (10)
C35—C36—H36	119.8	C19—C10—C11	112.36 (10)
C32—C33—H33	119.8	C19—C10—C15	105.00 (10)
C32—C33—C34	120.35 (12)	C11—C10—C15	108.10 (10)
C34—C33—H33	119.8	C24—C23—C22	119.97 (13)
C9—C4—C2	121.32 (12)	C24—C23—H23	120.0
C5—C4—C2	119.43 (12)	C22—C23—H23	120.0
C5—C4—C9	119.25 (12)	N62—C67—H67	119.6
C36—C35—H35	119.6	N62—C67—C66	120.89 (14)
C36—C35—C34	120.71 (12)	C66—C67—H67	119.6
C34—C35—H35	119.6	C22—C21—H21	119.9
C33—C34—C35	118.69 (12)	C20—C21—C22	120.23 (13)
C33—C34—C37	123.97 (11)	C20—C21—H21	119.9
C35—C34—C37	117.29 (11)	F44—C43—F46	106.43 (11)
C49—C50—C51	119.40 (12)	F44—C43—F45	107.53 (11)
C49—C50—C54	120.82 (12)	F44—C43—C37	111.05 (11)
C51—C50—C54	119.77 (12)	F46—C43—C37	111.60 (11)
C47—C48—H48	119.9	F45—C43—F46	106.54 (10)
C49—C48—C47	120.22 (12)	F45—C43—C37	113.33 (11)
C49—C48—H48	119.9	C67—C66—H66	120.6
C50—C49—C48	120.55 (12)	C67—C66—C65	118.71 (14)
C50—C49—H49	119.7	C65—C66—H66	120.6
C48—C49—H49	119.7	O27—C25—C22	113.69 (13)
C7—C8—H8	119.8	O26—C25—O27	124.54 (14)
C9—C8—C7	120.49 (12)	O26—C25—C22	121.72 (14)
C9—C8—H8	119.8	N62—C63—H63	119.5
C52—C51—C50	120.23 (12)	N62—C63—C64	121.10 (14)
C52—C51—H51	119.9	C64—C63—H63	119.5
C50—C51—H51	119.9	N56—C61—H61	120.0
O3—C2—C4	112.03 (11)	N56—C61—C60	120.06 (15)
O1—C2—O3	125.01 (12)	C60—C61—H61	120.0
O1—C2—C4	122.97 (12)	C63—C64—H64	120.7
C19—C24—H24	119.8	C63—C64—C65	118.65 (14)
C23—C24—C19	120.48 (12)	C65—C64—H64	120.7
C23—C24—H24	119.8	C66—C65—H65	120.1
C47—C37—C38	112.44 (10)	C64—C65—C66	119.83 (14)
C47—C37—C43	106.48 (10)	C64—C65—H65	120.1
C34—C37—C47	110.64 (10)	N56—C57—H57	119.7
C34—C37—C38	106.14 (10)	N56—C57—C58	120.64 (15)
C34—C37—C43	113.24 (10)	C58—C57—H57	119.7
C43—C37—C38	107.98 (10)	C61—C60—H60	120.2
F12—C11—F13	107.41 (10)	C61—C60—C59	119.52 (15)
F12—C11—C10	111.19 (11)	C59—C60—H60	120.2
F13—C11—C10	112.53 (11)	C57—C58—H58	120.5
F42—C11—F12	106.59 (10)	C57—C58—C59	119.01 (16)
F42—C11—F13	106.93 (10)	C59—C58—H58	120.5
F42—C11—C10	111.87 (10)	C60—C59—C58	119.07 (15)
C4—C9—H9	119.8	C60—C59—H59	120.5
C8—C9—C4	120.48 (12)	C58—C59—H59	120.5

F12—C11—C10—C7	−73.81 (13)	C48—C47—C52—C51	−2.13 (19)
F12—C11—C10—C19	49.66 (14)	C48—C47—C37—C34	142.26 (12)
F12—C11—C10—C15	165.06 (10)	C48—C47—C37—C38	23.77 (17)
F17—C15—C10—C7	−71.96 (13)	C48—C47—C37—C43	−94.29 (14)
F17—C15—C10—C19	165.75 (10)	C49—C50—C51—C52	2.7 (2)
F17—C15—C10—C11	45.62 (14)	C49—C50—C54—O53	−13.18 (19)
F13—C11—C10—C7	165.65 (10)	C49—C50—C54—O55	167.73 (13)
F13—C11—C10—C19	−70.88 (14)	C8—C7—C6—C5	−0.79 (19)
F13—C11—C10—C15	44.51 (14)	C8—C7—C10—C19	141.09 (12)
F16—C15—C10—C7	168.13 (10)	C8—C7—C10—C11	−95.37 (14)
F16—C15—C10—C19	45.84 (13)	C8—C7—C10—C15	23.00 (17)
F16—C15—C10—C11	−74.29 (13)	C51—C50—C49—C48	−1.5 (2)
F18—C15—C10—C7	48.59 (14)	C51—C50—C54—O53	165.83 (12)
F18—C15—C10—C19	−73.71 (13)	C51—C50—C54—O55	−13.26 (19)
F18—C15—C10—C11	166.17 (10)	C2—C4—C9—C8	−179.35 (12)
F42—C11—C10—C7	45.24 (14)	C2—C4—C5—C6	−179.14 (12)
F42—C11—C10—C19	168.71 (10)	C24—C19—C20—C21	1.51 (19)
F42—C11—C10—C15	−75.90 (13)	C24—C19—C10—C7	141.61 (12)
N56—C61—C60—C59	−1.0 (2)	C24—C19—C10—C11	21.26 (17)
N56—C57—C58—C59	−1.5 (3)	C24—C19—C10—C15	−96.00 (14)
N62—C67—C66—C65	0.4 (2)	C37—C47—C52—C51	179.52 (12)
N62—C63—C64—C65	0.0 (2)	C37—C47—C48—C49	−178.47 (12)
C47—C52—C51—C50	−0.9 (2)	C9—C4—C2—O3	−15.59 (17)
C47—C48—C49—C50	−1.5 (2)	C9—C4—C2—O1	163.94 (13)
C47—C37—C38—F40	50.14 (14)	C9—C4—C5—C6	1.4 (2)
C47—C37—C38—F41	−70.65 (14)	C5—C4—C2—O3	164.93 (12)
C47—C37—C38—F39	169.24 (11)	C5—C4—C2—O1	−15.6 (2)
C47—C37—C43—F44	−67.10 (13)	C5—C4—C9—C8	0.1 (2)
C47—C37—C43—F46	51.47 (14)	C20—C19—C24—C23	−0.35 (19)
C47—C37—C43—F45	171.75 (10)	C20—C19—C10—C7	−44.43 (15)
C31—C32—C33—C34	−1.22 (19)	C20—C19—C10—C11	−164.79 (11)
C31—C36—C35—C34	−0.94 (19)	C20—C19—C10—C15	77.96 (13)
C7—C8—C9—C4	−2.0 (2)	C6—C7—C8—C9	2.29 (19)
C52—C47—C48—C49	3.29 (19)	C6—C7—C10—C19	−42.64 (15)
C52—C47—C37—C34	−39.47 (15)	C6—C7—C10—C11	80.90 (14)
C52—C47—C37—C38	−157.96 (11)	C6—C7—C10—C15	−160.73 (11)
C52—C47—C37—C43	83.97 (14)	C38—C37—C43—F44	171.93 (10)
C32—C31—C29—O30	−176.34 (12)	C38—C37—C43—F46	−69.49 (13)
C32—C31—C29—O28	3.42 (18)	C38—C37—C43—F45	50.78 (14)
C32—C31—C36—C35	0.44 (19)	C54—C50—C49—C48	177.47 (12)
C32—C33—C34—C35	0.71 (19)	C54—C50—C51—C52	−176.32 (12)
C32—C33—C34—C37	178.22 (12)	C10—C7—C8—C9	178.54 (12)
C19—C24—C23—C22	−0.9 (2)	C10—C7—C6—C5	−177.23 (12)
C19—C20—C21—C22	−1.4 (2)	C10—C19—C24—C23	173.49 (12)
C29—C31—C32—C33	−178.96 (11)	C10—C19—C20—C21	−172.68 (12)
C29—C31—C36—C35	−179.97 (12)	C23—C22—C21—C20	0.1 (2)
C36—C31—C32—C33	0.64 (19)	C23—C22—C25—O27	−7.03 (19)
C36—C31—C29—O30	4.08 (18)	C23—C22—C25—O26	170.47 (16)
C36—C31—C29—O28	−176.17 (12)	C67—N62—C63—C64	0.0 (2)
C36—C35—C34—C33	0.36 (19)	C67—C66—C65—C64	−0.4 (2)
C36—C35—C34—C37	−177.31 (11)	C21—C22—C23—C24	1.1 (2)
C33—C34—C37—C47	133.38 (13)	C21—C22—C25—O27	174.16 (12)
C33—C34—C37—C38	−104.36 (14)	C21—C22—C25—O26	−8.3 (2)
C33—C34—C37—C43	13.94 (17)	C43—C37—C38—F40	167.32 (10)
C4—C5—C6—C7	−1.0 (2)	C43—C37—C38—F41	46.52 (14)
C35—C34—C37—C47	−49.08 (15)	C43—C37—C38—F39	−73.59 (13)
C35—C34—C37—C38	73.18 (14)	C25—C22—C23—C24	−177.72 (13)
C35—C34—C37—C43	−168.52 (11)	C25—C22—C21—C20	178.93 (13)
C34—C37—C38—F40	−70.96 (13)	C63—N62—C67—C66	−0.2 (2)
C34—C37—C38—F41	168.25 (10)	C63—C64—C65—C66	0.2 (2)
C34—C37—C38—F39	48.14 (14)	C61—N56—C57—C58	0.0 (2)
C34—C37—C43—F44	54.71 (14)	C61—C60—C59—C58	−0.5 (3)
C34—C37—C43—F46	173.28 (10)	C57—N56—C61—C60	1.3 (2)
C34—C37—C43—F45	−66.44 (14)	C57—C58—C59—C60	1.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O55ⁱ	0.84	1.75	2.5732 (13)	164
O27—H27···O28	0.84	1.68	2.5125 (13)	172
N56—H56···O30	0.88	1.79	2.6488 (15)	165
N62—H62···O53	0.88	1.67	2.5472 (15)	177

Symmetry code: (i) x−1, y, z.

Ethane-1,2-diaminium 4,4'-(1,1,1,3,3,3-hexafluoropropane-2,2-diyl)dibenzoate monohydrate (2) top