Two nonlinear optically responsive crown ether inclusion com­pounds based on a sulfonimide anion assembly

Organic amine crown ether supra­molecular com­pounds, based on crystal engineering design, have already made significant research progress in functional devices such as ferroelectrics, ferroelastics and nonlinear optical materials, especially those involving anilinium cations, which have attracted widespread attention. In com­parison, benzyl­ammonium cations have been less studied and most counter-ions are inorganic metal salt anions, crystallizing in centrosymmetric space groups without nonlinear optical (NLO) response. By changing the anion, we have obtained two types of crown ether inclusion com­pounds, namely, benzyl­ammonium bis­(methane­sulfon­yl)aza­nide–1,4,7,10,13,16-hexa­oxa­cyclo­octa­decane (1/1), C₇H₁₀N⁺·C₂H₆NO₄S₂⁻·C₁₂H₂₄O₆ or [(BA)(18-crown-6)][DMSA] [BA = benzyl­ammonium and DMSA = bis­(methane­sulfon­yl)aza­nide] and benzyl­ammonium (methane­sulfon­yl)(tri­fluoro­methyl­sulfon­yl)aza­nide–1,4,7,10,13,16-hexa­oxa­cyclo­octa­decane (1/1), C₇H₁₀N⁺·C₂H₃F₃NO₄S₂⁻·C₁₂H₂₄O₆ or [(BA)(18-crown-6)][TfNMs] [TfNMs = (methyl­sulfon­yl)(tri­fluoro­methyl­sul­fon­yl)aza­nide]. Both com­pounds crystallize in the polar chiral space group P2₁ at 100 K and exhibit a clear second harmonic generation (SHG) active characteristic, showing potential for use in quadratic nonlinear optical fields. Moreover, this work is the first to report crown-ether-based com­pounds using TfNMs as the counter-ion, enriching the choice of counter-anion for crown-ether-based com­pounds.

Computing details

Benzylammonium bis(methanesulfonyl)azanide; 1,4,7,10,13,16-hexaoxacyclooctadecane (18c6_ba_dmsa_100k_auto)

Crystal data

C7H10N^+·C2H6NO4S2^−·C12H24O6	F(000) = 584
Mr = 544.67	Dx = 1.370 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54184 Å
a = 7.99791 (11) Å	Cell parameters from 20406 reflections
b = 16.29632 (19) Å	θ = 4.3–72.1°
c = 10.52351 (13) Å	µ = 2.31 mm^−1
β = 105.6833 (13)°	T = 100 K
V = 1320.53 (3) Å^3	Plate, colourless
Z = 2	0.2 × 0.18 × 0.1 mm

Data collection

Rigaku XtaLAB Synergy-R DW diffractometer with a HyPix-Arc 150 detector	5016 independent reflections
Radiation source: Rotating-anode X-ray tube, Rigaku (Cu) X-ray Source	4939 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.035
Detector resolution: 10.0000 pixels mm^-1	θmax = 72.2°, θmin = 4.4°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2024)	k = −20→20
Tmin = 0.742, Tmax = 1.000	l = −12→12
25892 measured reflections

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0411P)^2 + 0.1601P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.025	(Δ/σ)max = 0.001
wR(F^2) = 0.067	Δρmax = 0.18 e Å^−3
S = 1.08	Δρmin = −0.22 e Å^−3
5016 reflections	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
350 parameters	Extinction coefficient: 0.0010 (3)
14 restraints	Absolute structure: Flack x determined using 2293 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Hydrogen site location: mixed	Absolute structure parameter: −0.022 (7)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.2705 (4)	0.48882 (15)	0.1531 (2)	0.0330 (6)
H1A	0.244327	0.460375	0.066824	0.040*
H1B	0.327415	0.541719	0.144637	0.040*
C2	0.1070 (4)	0.50383 (15)	0.1910 (2)	0.0326 (6)
H2A	0.025442	0.536266	0.121718	0.039*
H2B	0.050881	0.450963	0.200991	0.039*
C3	−0.0016 (3)	0.56991 (15)	0.3540 (3)	0.0304 (5)
H3A	−0.059527	0.520093	0.375313	0.036*
H3B	−0.085032	0.599809	0.282277	0.036*
C4	0.0557 (3)	0.62345 (15)	0.4734 (2)	0.0298 (5)
H4A	0.124865	0.670010	0.454629	0.036*
H4B	−0.046965	0.645862	0.497091	0.036*
C5	0.2110 (3)	0.62261 (15)	0.7000 (2)	0.0290 (5)
H5A	0.107429	0.643996	0.723628	0.035*
H5B	0.282793	0.669836	0.687564	0.035*
C6	0.3140 (3)	0.56824 (15)	0.8086 (2)	0.0283 (5)
H6A	0.336314	0.596879	0.894505	0.034*
H6B	0.248221	0.517383	0.813360	0.034*
C7	0.5826 (3)	0.49700 (15)	0.8787 (2)	0.0273 (5)
H7A	0.521910	0.444838	0.885003	0.033*
H7B	0.610111	0.524413	0.965827	0.033*
C8	0.7462 (3)	0.48027 (15)	0.8400 (2)	0.0278 (5)
H8A	0.802214	0.532591	0.826901	0.033*
H8B	0.828389	0.448884	0.910472	0.033*
C9	0.8521 (3)	0.41639 (17)	0.6741 (2)	0.0304 (5)
H9A	0.941136	0.387898	0.743948	0.036*
H9B	0.902890	0.468090	0.651991	0.036*
C10	0.7972 (3)	0.36315 (16)	0.5544 (3)	0.0302 (5)
H10A	0.900669	0.339956	0.532912	0.036*
H10B	0.725179	0.317170	0.571274	0.036*
C11	0.6509 (4)	0.36657 (17)	0.3269 (3)	0.0341 (6)
H11A	0.582481	0.317628	0.337370	0.041*
H11B	0.755550	0.348011	0.301931	0.041*
C12	0.5438 (4)	0.42185 (18)	0.2219 (2)	0.0360 (6)
H12A	0.607582	0.473476	0.218237	0.043*
H12B	0.520459	0.394679	0.134666	0.043*
O1	0.3840 (2)	0.43933 (10)	0.25223 (16)	0.0290 (4)
O2	0.1485 (2)	0.54769 (10)	0.31312 (15)	0.0277 (4)
O3	0.1586 (2)	0.57588 (10)	0.58084 (15)	0.0246 (3)
O4	0.4743 (2)	0.54867 (10)	0.78071 (15)	0.0247 (3)
O5	0.7026 (2)	0.43389 (10)	0.71980 (15)	0.0249 (3)
O6	0.7000 (2)	0.41154 (11)	0.44721 (16)	0.0285 (4)
C13	0.2426 (3)	0.38737 (13)	0.5409 (2)	0.0223 (4)
H13A	0.127238	0.401267	0.481654	0.027*
H13B	0.233177	0.388615	0.632804	0.027*
C14	0.2921 (3)	0.30217 (13)	0.5094 (2)	0.0202 (4)
C15	0.2381 (3)	0.27213 (14)	0.3808 (2)	0.0246 (5)
H15	0.168600	0.305325	0.312499	0.029*
C16	0.2855 (3)	0.19392 (15)	0.3525 (2)	0.0283 (5)
H16	0.248603	0.173647	0.264697	0.034*
C17	0.3866 (3)	0.14518 (15)	0.4516 (3)	0.0301 (5)
H17	0.419420	0.091698	0.431646	0.036*
C18	0.4400 (3)	0.17436 (16)	0.5799 (2)	0.0299 (5)
H18	0.509043	0.140855	0.647998	0.036*
C19	0.3922 (3)	0.25276 (16)	0.6090 (2)	0.0250 (4)
H19	0.428070	0.272607	0.697050	0.030*
N1	0.3720 (3)	0.45048 (12)	0.52557 (19)	0.0201 (4)
C20	0.2347 (3)	0.73941 (17)	0.1305 (2)	0.0297 (5)
H20A	0.183749	0.716567	0.197703	0.044*
H20B	0.282658	0.793887	0.158428	0.044*
H20C	0.327648	0.703197	0.119513	0.044*
C21A	−0.3408 (19)	0.7094 (9)	0.0072 (11)	0.042 (2)	0.56
H21A	−0.422670	0.733561	−0.070317	0.063*	0.56
H21B	−0.404679	0.687883	0.067353	0.063*	0.56
H21C	−0.276976	0.664672	−0.020878	0.063*	0.56
C21B	−0.363 (2)	0.7254 (10)	−0.0334 (14)	0.043 (3)	0.44
H21D	−0.314846	0.672678	−0.050994	0.065*	0.44
H21E	−0.400402	0.756839	−0.115701	0.065*	0.44
H21F	−0.462775	0.715850	0.001923	0.065*	0.44
N2	−0.0698 (2)	0.81010 (11)	0.00157 (18)	0.0222 (4)
O7	0.0071 (2)	0.66544 (11)	−0.05423 (16)	0.0282 (4)
O8	0.1535 (2)	0.78635 (13)	−0.11247 (17)	0.0367 (4)
O9A	−0.1055 (6)	0.7420 (2)	0.2092 (4)	0.0337 (9)	0.857
O10	−0.2899 (2)	0.85602 (11)	0.10712 (17)	0.0305 (4)
S1	0.07329 (6)	0.74763 (3)	−0.02052 (5)	0.02192 (13)
S2	−0.19687 (7)	0.78326 (3)	0.08678 (6)	0.02461 (14)
O9B	−0.150 (4)	0.7223 (13)	0.181 (2)	0.028 (5)	0.143
H1C	0.477 (4)	0.4442 (17)	0.586 (3)	0.021 (6)*
H1D	0.329 (4)	0.499 (2)	0.538 (3)	0.030 (7)*
H1E	0.382 (4)	0.4464 (18)	0.441 (3)	0.033 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0584 (17)	0.0219 (12)	0.0162 (10)	−0.0063 (11)	0.0057 (11)	0.0000 (9)
C2	0.0469 (15)	0.0235 (12)	0.0196 (11)	−0.0053 (10)	−0.0046 (10)	0.0005 (9)
C3	0.0273 (12)	0.0265 (12)	0.0332 (13)	0.0028 (10)	0.0012 (10)	0.0079 (10)
C4	0.0309 (12)	0.0217 (12)	0.0369 (14)	0.0058 (10)	0.0093 (11)	0.0048 (10)
C5	0.0340 (12)	0.0242 (12)	0.0308 (12)	−0.0002 (10)	0.0123 (10)	−0.0075 (10)
C6	0.0329 (13)	0.0308 (13)	0.0250 (11)	−0.0048 (10)	0.0142 (10)	−0.0065 (9)
C7	0.0381 (13)	0.0246 (11)	0.0168 (10)	−0.0057 (10)	0.0031 (9)	0.0025 (8)
C8	0.0299 (12)	0.0245 (12)	0.0231 (11)	−0.0062 (10)	−0.0030 (9)	0.0030 (9)
C9	0.0193 (11)	0.0355 (13)	0.0358 (13)	0.0001 (10)	0.0064 (10)	0.0095 (11)
C10	0.0256 (12)	0.0260 (12)	0.0427 (14)	0.0036 (9)	0.0158 (10)	0.0050 (11)
C11	0.0406 (14)	0.0322 (13)	0.0359 (13)	−0.0022 (11)	0.0212 (11)	−0.0104 (11)
C12	0.0483 (16)	0.0398 (15)	0.0251 (12)	−0.0088 (12)	0.0191 (11)	−0.0069 (11)
O1	0.0406 (10)	0.0283 (9)	0.0191 (8)	−0.0041 (7)	0.0095 (7)	−0.0002 (7)
O2	0.0313 (8)	0.0268 (9)	0.0206 (7)	−0.0010 (7)	−0.0002 (6)	−0.0016 (6)
O3	0.0296 (8)	0.0199 (8)	0.0244 (8)	0.0032 (6)	0.0074 (6)	−0.0008 (6)
O4	0.0297 (8)	0.0264 (8)	0.0190 (7)	−0.0005 (7)	0.0086 (6)	0.0021 (6)
O5	0.0217 (8)	0.0273 (8)	0.0238 (8)	−0.0017 (6)	0.0031 (6)	0.0007 (7)
O6	0.0346 (9)	0.0254 (9)	0.0280 (9)	−0.0004 (7)	0.0128 (7)	−0.0007 (7)
C13	0.0225 (11)	0.0202 (11)	0.0253 (11)	−0.0012 (9)	0.0084 (9)	0.0000 (8)
C14	0.0206 (10)	0.0192 (11)	0.0215 (10)	−0.0028 (8)	0.0070 (8)	0.0003 (8)
C15	0.0292 (11)	0.0218 (12)	0.0209 (10)	−0.0037 (9)	0.0038 (9)	0.0016 (8)
C16	0.0359 (13)	0.0268 (12)	0.0216 (11)	−0.0059 (10)	0.0067 (10)	−0.0049 (9)
C17	0.0327 (13)	0.0225 (12)	0.0365 (13)	0.0008 (10)	0.0119 (10)	−0.0052 (10)
C18	0.0302 (12)	0.0266 (12)	0.0295 (12)	0.0062 (10)	0.0021 (10)	0.0021 (10)
C19	0.0256 (10)	0.0266 (11)	0.0215 (10)	0.0002 (10)	0.0040 (8)	−0.0012 (9)
N1	0.0236 (10)	0.0174 (9)	0.0185 (9)	−0.0018 (7)	0.0045 (8)	−0.0016 (7)
C20	0.0261 (11)	0.0337 (13)	0.0265 (11)	0.0056 (10)	0.0025 (9)	−0.0052 (10)
C21A	0.034 (4)	0.044 (5)	0.047 (5)	−0.008 (3)	0.013 (4)	−0.011 (4)
C21B	0.023 (5)	0.046 (7)	0.066 (8)	−0.019 (5)	0.019 (5)	−0.037 (6)
N2	0.0258 (10)	0.0184 (9)	0.0215 (9)	0.0013 (7)	0.0047 (7)	0.0012 (7)
O7	0.0319 (9)	0.0242 (8)	0.0287 (8)	−0.0012 (7)	0.0083 (7)	−0.0063 (7)
O8	0.0444 (10)	0.0416 (10)	0.0299 (9)	−0.0059 (9)	0.0201 (8)	0.0007 (8)
O9A	0.043 (2)	0.028 (2)	0.0362 (19)	0.0091 (17)	0.0219 (15)	0.0123 (17)
O10	0.0316 (9)	0.0278 (9)	0.0314 (9)	0.0081 (7)	0.0076 (7)	−0.0030 (7)
S1	0.0237 (3)	0.0243 (3)	0.0183 (2)	−0.0005 (2)	0.00668 (19)	−0.0019 (2)
S2	0.0247 (3)	0.0202 (3)	0.0308 (3)	0.0011 (2)	0.0107 (2)	−0.0017 (2)
O9B	0.048 (15)	0.012 (8)	0.031 (10)	−0.007 (7)	0.022 (9)	−0.001 (7)

Geometric parameters (Å, º)

C1—H1A	0.9900	C12—H12B	0.9900
C1—H1B	0.9900	C12—O1	1.427 (3)
C1—C2	1.487 (4)	C13—H13A	0.9900
C1—O1	1.432 (3)	C13—H13B	0.9900
C2—H2A	0.9900	C13—C14	1.505 (3)
C2—H2B	0.9900	C13—N1	1.499 (3)
C2—O2	1.429 (3)	C14—C15	1.393 (3)
C3—H3A	0.9900	C14—C19	1.390 (3)
C3—H3B	0.9900	C15—H15	0.9500
C3—C4	1.497 (4)	C15—C16	1.385 (3)
C3—O2	1.427 (3)	C16—H16	0.9500
C4—H4A	0.9900	C16—C17	1.384 (4)
C4—H4B	0.9900	C17—H17	0.9500
C4—O3	1.433 (3)	C17—C18	1.386 (4)
C5—H5A	0.9900	C18—H18	0.9500
C5—H5B	0.9900	C18—C19	1.391 (4)
C5—C6	1.503 (3)	C19—H19	0.9500
C5—O3	1.430 (3)	N1—H1C	0.91 (3)
C6—H6A	0.9900	N1—H1D	0.88 (3)
C6—H6B	0.9900	N1—H1E	0.92 (3)
C6—O4	1.427 (3)	C20—H20A	0.9800
C7—H7A	0.9900	C20—H20B	0.9800
C7—H7B	0.9900	C20—H20C	0.9800
C7—C8	1.497 (4)	C20—S1	1.761 (2)
C7—O4	1.428 (3)	C21A—H21A	0.9800
C8—H8A	0.9900	C21A—H21B	0.9800
C8—H8B	0.9900	C21A—H21C	0.9800
C8—O5	1.433 (3)	C21A—S2	1.719 (15)
C9—H9A	0.9900	C21B—H21D	0.9800
C9—H9B	0.9900	C21B—H21E	0.9800
C9—C10	1.494 (4)	C21B—H21F	0.9800
C9—O5	1.433 (3)	C21B—S2	1.829 (14)
C10—H10A	0.9900	N2—S1	1.5950 (19)
C10—H10B	0.9900	N2—S2	1.5878 (19)
C10—O6	1.423 (3)	O7—S1	1.4487 (18)
C11—H11A	0.9900	O8—S1	1.4429 (18)
C11—H11B	0.9900	O9A—S2	1.462 (4)
C11—C12	1.501 (4)	O10—S2	1.4464 (17)
C11—O6	1.424 (3)	S2—O9B	1.38 (2)
C12—H12A	0.9900
H1A—C1—H1B	108.3	C12—O1—C1	112.26 (19)
C2—C1—H1A	109.9	C3—O2—C2	112.83 (19)
C2—C1—H1B	109.9	C5—O3—C4	111.93 (18)
O1—C1—H1A	109.9	C6—O4—C7	112.75 (17)
O1—C1—H1B	109.9	C9—O5—C8	112.05 (18)
O1—C1—C2	109.10 (19)	C10—O6—C11	112.36 (19)
C1—C2—H2A	110.0	H13A—C13—H13B	107.9
C1—C2—H2B	110.0	C14—C13—H13A	109.2
H2A—C2—H2B	108.4	C14—C13—H13B	109.2
O2—C2—C1	108.4 (2)	N1—C13—H13A	109.2
O2—C2—H2A	110.0	N1—C13—H13B	109.2
O2—C2—H2B	110.0	N1—C13—C14	112.23 (18)
H3A—C3—H3B	108.4	C15—C14—C13	120.47 (19)
C4—C3—H3A	110.1	C19—C14—C13	120.02 (19)
C4—C3—H3B	110.1	C19—C14—C15	119.5 (2)
O2—C3—H3A	110.1	C14—C15—H15	120.0
O2—C3—H3B	110.1	C16—C15—C14	120.1 (2)
O2—C3—C4	108.02 (19)	C16—C15—H15	120.0
C3—C4—H4A	109.9	C15—C16—H16	119.9
C3—C4—H4B	109.9	C17—C16—C15	120.3 (2)
H4A—C4—H4B	108.3	C17—C16—H16	119.9
O3—C4—C3	109.10 (19)	C16—C17—H17	120.0
O3—C4—H4A	109.9	C16—C17—C18	120.0 (2)
O3—C4—H4B	109.9	C18—C17—H17	120.0
H5A—C5—H5B	108.3	C17—C18—H18	120.0
C6—C5—H5A	109.9	C17—C18—C19	119.9 (2)
C6—C5—H5B	109.9	C19—C18—H18	120.0
O3—C5—H5A	109.9	C14—C19—C18	120.2 (2)
O3—C5—H5B	109.9	C14—C19—H19	119.9
O3—C5—C6	108.85 (19)	C18—C19—H19	119.9
C5—C6—H6A	110.0	C13—N1—H1C	112.4 (17)
C5—C6—H6B	110.0	C13—N1—H1D	106.8 (19)
H6A—C6—H6B	108.4	C13—N1—H1E	107.3 (19)
O4—C6—C5	108.29 (18)	H1C—N1—H1D	109 (3)
O4—C6—H6A	110.0	H1C—N1—H1E	111 (2)
O4—C6—H6B	110.0	H1D—N1—H1E	110 (3)
H7A—C7—H7B	108.4	H20A—C20—H20B	109.5
C8—C7—H7A	110.0	H20A—C20—H20C	109.5
C8—C7—H7B	110.0	H20B—C20—H20C	109.5
O4—C7—H7A	110.0	S1—C20—H20A	109.5
O4—C7—H7B	110.0	S1—C20—H20B	109.5
O4—C7—C8	108.38 (18)	S1—C20—H20C	109.5
C7—C8—H8A	110.0	H21A—C21A—H21B	109.5
C7—C8—H8B	110.0	H21A—C21A—H21C	109.5
H8A—C8—H8B	108.4	H21B—C21A—H21C	109.5
O5—C8—C7	108.31 (19)	S2—C21A—H21A	109.5
O5—C8—H8A	110.0	S2—C21A—H21B	109.5
O5—C8—H8B	110.0	S2—C21A—H21C	109.5
H9A—C9—H9B	108.4	H21D—C21B—H21E	109.5
C10—C9—H9A	110.0	H21D—C21B—H21F	109.5
C10—C9—H9B	110.0	H21E—C21B—H21F	109.5
O5—C9—H9A	110.0	S2—C21B—H21D	109.5
O5—C9—H9B	110.0	S2—C21B—H21E	109.5
O5—C9—C10	108.48 (18)	S2—C21B—H21F	109.5
C9—C10—H10A	110.0	S2—N2—S1	120.03 (12)
C9—C10—H10B	110.0	N2—S1—C20	107.27 (11)
H10A—C10—H10B	108.3	O7—S1—C20	106.31 (12)
O6—C10—C9	108.6 (2)	O7—S1—N2	113.38 (10)
O6—C10—H10A	110.0	O8—S1—C20	106.74 (12)
O6—C10—H10B	110.0	O8—S1—N2	106.58 (11)
H11A—C11—H11B	108.4	O8—S1—O7	116.07 (11)
C12—C11—H11A	110.1	N2—S2—C21A	111.4 (4)
C12—C11—H11B	110.1	N2—S2—C21B	102.0 (5)
O6—C11—H11A	110.1	O9A—S2—C21A	102.5 (4)
O6—C11—H11B	110.1	O9A—S2—N2	112.4 (2)
O6—C11—C12	108.1 (2)	O10—S2—C21A	110.0 (5)
C11—C12—H12A	109.9	O10—S2—C21B	102.6 (5)
C11—C12—H12B	109.9	O10—S2—N2	106.94 (10)
H12A—C12—H12B	108.3	O10—S2—O9A	113.7 (2)
O1—C12—C11	108.78 (19)	O9B—S2—C21B	97.6 (9)
O1—C12—H12A	109.9	O9B—S2—N2	120.7 (14)
O1—C12—H12B	109.9	O9B—S2—O10	122.3 (14)
C1—C2—O2—C3	176.16 (19)	C13—C14—C15—C16	179.4 (2)
C2—C1—O1—C12	179.6 (2)	C13—C14—C19—C18	−179.3 (2)
C3—C4—O3—C5	−177.31 (19)	C14—C15—C16—C17	0.1 (3)
C4—C3—O2—C2	−173.53 (18)	C15—C14—C19—C18	0.9 (3)
C5—C6—O4—C7	179.91 (18)	C15—C16—C17—C18	0.4 (4)
C6—C5—O3—C4	178.54 (18)	C16—C17—C18—C19	−0.2 (4)
C7—C8—O5—C9	178.91 (19)	C17—C18—C19—C14	−0.5 (4)
C8—C7—O4—C6	179.92 (19)	C19—C14—C15—C16	−0.7 (3)
C9—C10—O6—C11	176.60 (18)	N1—C13—C14—C15	−89.0 (2)
C10—C9—O5—C8	176.04 (19)	N1—C13—C14—C19	91.1 (2)
C11—C12—O1—C1	−177.3 (2)	S1—N2—S2—C21A	−69.1 (5)
C12—C11—O6—C10	177.87 (19)	S1—N2—S2—C21B	−82.0 (5)
O1—C1—C2—O2	61.8 (2)	S1—N2—S2—O9A	45.3 (2)
O2—C3—C4—O3	−67.0 (2)	S1—N2—S2—O10	170.69 (12)
O3—C5—C6—O4	68.2 (2)	S1—N2—S2—O9B	24.5 (10)
O4—C7—C8—O5	−65.0 (2)	S2—N2—S1—C20	−72.10 (16)
O5—C9—C10—O6	72.4 (2)	S2—N2—S1—O7	44.96 (16)
O6—C11—C12—O1	−66.9 (3)	S2—N2—S1—O8	173.87 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O5	0.91 (3)	1.98 (3)	2.885 (3)	178 (3)
N1—H1D···O3	0.88 (3)	2.00 (3)	2.822 (3)	156 (3)
N1—H1E···O1	0.92 (3)	1.99 (3)	2.910 (3)	176 (3)

Benzylammonium (methanesulfonyl)(trifluoromethylsulfonyl)azanide–1,4,7,10,13,16-hexaoxacyclooctadecane (1/1) (18c6_metfsa_ba_100k_auto)

Crystal data

C7H10N^+·C2H3F3NO4S2^−·C12H24O6	F(000) = 632
Mr = 598.64	Dx = 1.439 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54184 Å
a = 8.23545 (13) Å	Cell parameters from 21354 reflections
b = 16.4434 (2) Å	θ = 2.7–72.1°
c = 10.58330 (14) Å	µ = 2.42 mm^−1
β = 105.4332 (15)°	T = 100 K
V = 1381.50 (3) Å^3	Prism, colourless
Z = 2	0.2 × 0.16 × 0.12 mm

Data collection

Rigaku XtaLAB Synergy-R DW diffractometer with a HyPix-Arc 150 detector	5223 independent reflections
Radiation source: Rotating-anode X-ray tube, Rigaku (Cu) X-ray Source	5175 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.030
Detector resolution: 10.0000 pixels mm^-1	θmax = 72.2°, θmin = 4.3°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2024)	k = −20→20
Tmin = 0.679, Tmax = 1.000	l = −11→13
26683 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.036	w = 1/[σ^2(Fo^2) + (0.0567P)^2 + 0.7608P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.098	(Δ/σ)max = 0.001
S = 1.06	Δρmax = 0.69 e Å^−3
5223 reflections	Δρmin = −0.47 e Å^−3
344 parameters	Absolute structure: Flack x determined using 2382 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
29 restraints	Absolute structure parameter: −0.004 (6)
Primary atom site location: dual

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	1.08457 (11)	0.23084 (6)	0.97709 (8)	0.0355 (2)
S2	0.83287 (10)	0.21299 (5)	1.10910 (7)	0.02498 (18)
F1	0.7679 (3)	0.35817 (14)	1.0015 (3)	0.0481 (6)
F2	0.5772 (3)	0.26802 (19)	0.9236 (3)	0.0541 (7)
F3	0.6027 (3)	0.32135 (15)	1.1149 (2)	0.0437 (6)
O7	1.1488 (5)	0.1741 (3)	0.8986 (4)	0.0665 (11)
O8	1.0430 (4)	0.3105 (2)	0.9245 (3)	0.0523 (8)
O9	0.7223 (4)	0.14972 (17)	1.1273 (3)	0.0376 (6)
O10	0.9347 (3)	0.25157 (16)	1.2248 (2)	0.0345 (6)
N2	0.9264 (4)	0.18473 (19)	1.0073 (3)	0.0308 (6)
C20	1.2401 (5)	0.2431 (3)	1.1253 (4)	0.0411 (9)
H20A	1.336274	0.272417	1.109291	0.062*
H20B	1.277071	0.189573	1.162799	0.062*
H20C	1.193828	0.274153	1.186759	0.062*
C21	0.6887 (4)	0.2926 (2)	1.0335 (3)	0.0285 (5)
O1	0.6887 (3)	0.56186 (15)	0.7047 (2)	0.0281 (5)
O2	0.4537 (3)	0.45452 (15)	0.7650 (2)	0.0275 (5)
O3	0.1516 (3)	0.42358 (14)	0.5714 (2)	0.0263 (5)
O4	0.1463 (3)	0.44650 (15)	0.3040 (2)	0.0291 (5)
O5	0.3777 (4)	0.55519 (16)	0.2445 (2)	0.0319 (5)
O6	0.6857 (3)	0.58173 (16)	0.4362 (3)	0.0330 (6)
C1	0.7245 (4)	0.5169 (2)	0.8245 (3)	0.0346 (8)
H1A	0.806065	0.546922	0.894600	0.041*
H1B	0.773600	0.463343	0.813018	0.041*
C2	0.5572 (4)	0.5057 (2)	0.8610 (3)	0.0315 (8)
H2A	0.577717	0.480569	0.948823	0.038*
H2B	0.501804	0.558952	0.862534	0.038*
C3	0.3031 (5)	0.4336 (2)	0.7975 (3)	0.0327 (8)
H3A	0.237075	0.483133	0.803116	0.039*
H3B	0.329223	0.405490	0.883251	0.039*
C4	0.2024 (5)	0.3772 (2)	0.6889 (3)	0.0335 (8)
H4A	0.273244	0.330754	0.676507	0.040*
H4B	0.102446	0.355575	0.712863	0.040*
C5	0.0500 (5)	0.3759 (2)	0.4665 (3)	0.0335 (8)
H5A	−0.051806	0.356191	0.489899	0.040*
H5B	0.114447	0.328107	0.449662	0.040*
C6	−0.0006 (5)	0.4298 (2)	0.3436 (3)	0.0364 (9)
H6A	−0.084048	0.401355	0.272704	0.044*
H6B	−0.051579	0.481123	0.363656	0.044*
C7	0.1084 (4)	0.4906 (2)	0.1835 (3)	0.0400 (9)
H7A	0.054165	0.543086	0.193587	0.048*
H7B	0.030015	0.458949	0.113644	0.048*
C8	0.2744 (5)	0.5057 (2)	0.1469 (3)	0.0391 (9)
H8A	0.331400	0.453341	0.141289	0.047*
H8B	0.251651	0.533033	0.060624	0.047*
C9	0.5323 (6)	0.5754 (3)	0.2130 (4)	0.0435 (10)
H9A	0.507446	0.604061	0.127753	0.052*
H9B	0.595337	0.525067	0.205796	0.052*
C10	0.6353 (6)	0.6282 (3)	0.3177 (4)	0.0415 (9)
H10A	0.735857	0.647876	0.292412	0.050*
H10B	0.568536	0.676013	0.330935	0.050*
C11	0.7917 (5)	0.6264 (2)	0.5417 (4)	0.0356 (8)
H11A	0.732453	0.675518	0.560184	0.043*
H11B	0.895359	0.643710	0.518688	0.043*
C12	0.8354 (4)	0.5726 (2)	0.6589 (4)	0.0360 (8)
H12A	0.875287	0.519280	0.635623	0.043*
H12B	0.926611	0.597488	0.728510	0.043*
N1	0.3657 (4)	0.54499 (16)	0.5130 (3)	0.0198 (5)
H1C	0.459 (4)	0.548 (3)	0.562 (4)	0.024 (10)*
H1D	0.376 (5)	0.548 (3)	0.440 (3)	0.029 (11)*
H1E	0.325 (5)	0.502 (2)	0.527 (4)	0.033 (11)*
C13	0.2436 (4)	0.60808 (19)	0.5308 (3)	0.0229 (6)
H13A	0.235025	0.606031	0.622306	0.027*
H13B	0.131051	0.595535	0.472299	0.027*
C18	0.4488 (3)	0.81575 (12)	0.57355 (18)	0.0339 (8)
H18	0.521209	0.846953	0.641039	0.041*
C19	0.3996 (3)	0.73821 (12)	0.60049 (15)	0.0271 (7)
H19	0.438471	0.716424	0.686398	0.033*
C14	0.2937 (3)	0.69256 (9)	0.50174 (18)	0.0186 (6)
C15	0.2368 (3)	0.72444 (12)	0.37605 (16)	0.0266 (7)
H15	0.164397	0.693234	0.308556	0.032*
C16	0.2860 (3)	0.80197 (12)	0.34910 (15)	0.0304 (7)
H16	0.247132	0.823762	0.263195	0.036*
C17	0.3919 (3)	0.84763 (10)	0.4479 (2)	0.0312 (7)
H17	0.425538	0.900622	0.429434	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0338 (4)	0.0472 (6)	0.0260 (4)	−0.0048 (4)	0.0087 (3)	0.0032 (4)
S2	0.0298 (4)	0.0220 (3)	0.0231 (3)	−0.0011 (3)	0.0070 (3)	0.0019 (3)
F1	0.0526 (14)	0.0317 (12)	0.0623 (16)	0.0049 (11)	0.0191 (12)	0.0195 (11)
F2	0.0436 (13)	0.0660 (17)	0.0409 (13)	0.0052 (12)	−0.0092 (10)	0.0047 (12)
F3	0.0394 (12)	0.0480 (14)	0.0467 (13)	0.0129 (10)	0.0164 (10)	0.0048 (11)
O7	0.0517 (19)	0.098 (3)	0.060 (2)	−0.0084 (19)	0.0340 (17)	−0.028 (2)
O8	0.0410 (16)	0.066 (2)	0.0460 (17)	−0.0074 (14)	0.0048 (13)	0.0317 (15)
O9	0.0460 (16)	0.0347 (14)	0.0350 (14)	−0.0094 (12)	0.0158 (12)	0.0034 (11)
O10	0.0409 (14)	0.0335 (14)	0.0257 (12)	0.0021 (11)	0.0027 (10)	−0.0022 (10)
N2	0.0341 (16)	0.0299 (15)	0.0278 (14)	−0.0029 (12)	0.0072 (12)	−0.0019 (12)
C20	0.0326 (18)	0.048 (2)	0.0368 (19)	−0.0113 (17)	−0.0010 (15)	0.0124 (18)
C21	0.0285 (9)	0.0300 (9)	0.0269 (9)	−0.0009 (8)	0.0069 (8)	0.0012 (8)
O1	0.0231 (11)	0.0264 (12)	0.0322 (12)	0.0001 (9)	0.0027 (9)	−0.0033 (10)
O2	0.0359 (12)	0.0287 (12)	0.0190 (10)	0.0004 (10)	0.0092 (9)	−0.0030 (9)
O3	0.0325 (12)	0.0207 (11)	0.0271 (11)	−0.0053 (10)	0.0104 (10)	−0.0009 (9)
O4	0.0334 (12)	0.0260 (12)	0.0238 (11)	0.0003 (10)	0.0007 (10)	0.0006 (9)
O5	0.0482 (15)	0.0300 (12)	0.0200 (11)	0.0049 (11)	0.0136 (10)	0.0003 (9)
O6	0.0353 (13)	0.0295 (13)	0.0387 (14)	0.0013 (11)	0.0175 (11)	0.0020 (11)
C1	0.0349 (19)	0.0308 (19)	0.0296 (17)	0.0055 (15)	−0.0062 (14)	−0.0053 (14)
C2	0.042 (2)	0.0289 (18)	0.0201 (15)	0.0059 (15)	0.0029 (14)	−0.0041 (13)
C3	0.044 (2)	0.0352 (19)	0.0244 (16)	0.0006 (16)	0.0187 (15)	0.0029 (14)
C4	0.044 (2)	0.0272 (18)	0.0336 (19)	−0.0048 (15)	0.0168 (16)	0.0069 (14)
C5	0.0362 (19)	0.0247 (18)	0.040 (2)	−0.0122 (14)	0.0108 (16)	−0.0087 (14)
C6	0.0339 (19)	0.0304 (19)	0.0380 (19)	−0.0028 (15)	−0.0025 (16)	−0.0095 (15)
C7	0.060 (3)	0.0266 (18)	0.0220 (16)	0.0039 (17)	−0.0084 (17)	−0.0014 (14)
C8	0.067 (3)	0.0310 (19)	0.0176 (15)	0.0057 (18)	0.0078 (16)	−0.0006 (14)
C9	0.056 (2)	0.051 (2)	0.0328 (19)	0.013 (2)	0.0266 (18)	0.0124 (18)
C10	0.050 (2)	0.039 (2)	0.046 (2)	0.0050 (18)	0.0311 (19)	0.0142 (17)
C11	0.0278 (18)	0.0274 (18)	0.057 (2)	−0.0044 (15)	0.0208 (17)	−0.0068 (17)
C12	0.0220 (16)	0.0332 (19)	0.052 (2)	−0.0006 (14)	0.0078 (15)	−0.0125 (17)
N1	0.0242 (14)	0.0175 (13)	0.0180 (13)	−0.0017 (11)	0.0061 (11)	−0.0010 (10)
C13	0.0243 (16)	0.0189 (14)	0.0276 (16)	0.0012 (12)	0.0109 (13)	0.0005 (12)
C18	0.039 (2)	0.0266 (18)	0.0304 (18)	−0.0122 (15)	−0.0017 (14)	−0.0015 (14)
C19	0.0335 (17)	0.0241 (15)	0.0219 (14)	−0.0028 (13)	0.0041 (12)	0.0012 (13)
C14	0.0193 (14)	0.0166 (14)	0.0214 (14)	0.0010 (11)	0.0080 (11)	−0.0013 (11)
C15	0.0350 (16)	0.0201 (16)	0.0222 (14)	0.0027 (13)	0.0032 (12)	−0.0027 (12)
C16	0.043 (2)	0.0256 (17)	0.0241 (16)	0.0049 (14)	0.0111 (14)	0.0041 (13)
C17	0.0358 (18)	0.0221 (16)	0.0377 (19)	−0.0037 (14)	0.0131 (15)	0.0044 (14)

Geometric parameters (Å, º)

S1—O7	1.440 (4)	C5—H5B	0.9900
S1—O8	1.428 (3)	C5—C6	1.5377 (14)
S1—N2	1.611 (3)	C6—H6A	0.9900
S1—C20	1.753 (4)	C6—H6B	0.9900
S2—O9	1.429 (3)	C7—H7A	0.9900
S2—O10	1.435 (3)	C7—H7B	0.9900
S2—N2	1.553 (3)	C7—C8	1.5369 (14)
S2—C21	1.804 (4)	C8—H8A	0.9900
F1—C21	1.350 (4)	C8—H8B	0.9900
F2—C21	1.338 (4)	C9—H9A	0.9900
F3—C21	1.339 (4)	C9—H9B	0.9900
C20—H20A	0.9800	C9—C10	1.484 (7)
C20—H20B	0.9800	C10—H10A	0.9900
C20—H20C	0.9800	C10—H10B	0.9900
O1—C1	1.429 (4)	C11—H11A	0.9900
O1—C12	1.427 (4)	C11—H11B	0.9900
O2—C2	1.416 (4)	C11—C12	1.487 (6)
O2—C3	1.414 (4)	C12—H12A	0.9900
O3—C4	1.423 (4)	C12—H12B	0.9900
O3—C5	1.433 (4)	N1—H1C	0.81 (3)
O4—C6	1.408 (5)	N1—H1D	0.80 (3)
O4—C7	1.428 (4)	N1—H1E	0.81 (3)
O5—C8	1.409 (5)	N1—C13	1.491 (4)
O5—C9	1.438 (5)	C13—H13A	0.9900
O6—C10	1.433 (5)	C13—H13B	0.9900
O6—C11	1.425 (5)	C13—C14	1.504 (3)
C1—H1A	0.9900	C18—H18	0.9500
C1—H1B	0.9900	C18—C19	1.3900
C1—C2	1.5378 (14)	C18—C17	1.3900
C2—H2A	0.9900	C19—H19	0.9500
C2—H2B	0.9900	C19—C14	1.3900
C3—H3A	0.9900	C14—C15	1.3900
C3—H3B	0.9900	C15—H15	0.9500
C3—C4	1.5372 (14)	C15—C16	1.3900
C4—H4A	0.9900	C16—H16	0.9500
C4—H4B	0.9900	C16—C17	1.3900
C5—H5A	0.9900	C17—H17	0.9500
O7—S1—N2	104.5 (2)	O4—C7—H7A	110.1
O7—S1—C20	107.3 (2)	O4—C7—H7B	110.1
O8—S1—O7	117.1 (2)	O4—C7—C8	108.0 (3)
O8—S1—N2	112.73 (18)	H7A—C7—H7B	108.4
O8—S1—C20	106.6 (2)	C8—C7—H7A	110.1
N2—S1—C20	108.26 (17)	C8—C7—H7B	110.1
O9—S2—O10	117.09 (16)	O5—C8—C7	108.2 (3)
O9—S2—N2	109.11 (16)	O5—C8—H8A	110.1
O9—S2—C21	102.72 (17)	O5—C8—H8B	110.1
O10—S2—N2	116.04 (16)	C7—C8—H8A	110.1
O10—S2—C21	102.95 (16)	C7—C8—H8B	110.1
N2—S2—C21	107.37 (16)	H8A—C8—H8B	108.4
S2—N2—S1	125.0 (2)	O5—C9—H9A	109.9
S1—C20—H20A	109.5	O5—C9—H9B	109.9
S1—C20—H20B	109.5	O5—C9—C10	109.1 (3)
S1—C20—H20C	109.5	H9A—C9—H9B	108.3
H20A—C20—H20B	109.5	C10—C9—H9A	109.9
H20A—C20—H20C	109.5	C10—C9—H9B	109.9
H20B—C20—H20C	109.5	O6—C10—C9	108.4 (3)
F1—C21—S2	112.7 (2)	O6—C10—H10A	110.0
F2—C21—S2	112.7 (3)	O6—C10—H10B	110.0
F2—C21—F1	106.8 (3)	C9—C10—H10A	110.0
F2—C21—F3	107.9 (3)	C9—C10—H10B	110.0
F3—C21—S2	111.6 (2)	H10A—C10—H10B	108.4
F3—C21—F1	104.6 (3)	O6—C11—H11A	110.1
C12—O1—C1	111.8 (3)	O6—C11—H11B	110.1
C3—O2—C2	111.7 (2)	O6—C11—C12	108.0 (3)
C4—O3—C5	111.0 (2)	H11A—C11—H11B	108.4
C6—O4—C7	111.3 (2)	C12—C11—H11A	110.1
C8—O5—C9	111.3 (3)	C12—C11—H11B	110.1
C11—O6—C10	112.7 (3)	O1—C12—C11	108.5 (3)
O1—C1—H1A	110.3	O1—C12—H12A	110.0
O1—C1—H1B	110.3	O1—C12—H12B	110.0
O1—C1—C2	107.3 (3)	C11—C12—H12A	110.0
H1A—C1—H1B	108.5	C11—C12—H12B	110.0
C2—C1—H1A	110.3	H12A—C12—H12B	108.4
C2—C1—H1B	110.3	H1C—N1—H1D	107 (4)
O2—C2—C1	107.5 (3)	H1C—N1—H1E	108 (4)
O2—C2—H2A	110.2	H1D—N1—H1E	112 (4)
O2—C2—H2B	110.2	C13—N1—H1C	115 (3)
C1—C2—H2A	110.2	C13—N1—H1D	109 (3)
C1—C2—H2B	110.2	C13—N1—H1E	105 (3)
H2A—C2—H2B	108.5	N1—C13—H13A	109.0
O2—C3—H3A	110.2	N1—C13—H13B	109.0
O2—C3—H3B	110.2	N1—C13—C14	112.7 (2)
O2—C3—C4	107.4 (3)	H13A—C13—H13B	107.8
H3A—C3—H3B	108.5	C14—C13—H13A	109.0
C4—C3—H3A	110.2	C14—C13—H13B	109.0
C4—C3—H3B	110.2	C19—C18—H18	120.0
O3—C4—C3	107.7 (3)	C19—C18—C17	120.0
O3—C4—H4A	110.2	C17—C18—H18	120.0
O3—C4—H4B	110.2	C18—C19—H19	120.0
C3—C4—H4A	110.2	C18—C19—C14	120.0
C3—C4—H4B	110.2	C14—C19—H19	120.0
H4A—C4—H4B	108.5	C19—C14—C13	119.76 (17)
O3—C5—H5A	110.1	C15—C14—C13	120.23 (17)
O3—C5—H5B	110.1	C15—C14—C19	120.0
O3—C5—C6	108.1 (3)	C14—C15—H15	120.0
H5A—C5—H5B	108.4	C16—C15—C14	120.0
C6—C5—H5A	110.1	C16—C15—H15	120.0
C6—C5—H5B	110.1	C15—C16—H16	120.0
O4—C6—C5	107.6 (3)	C15—C16—C17	120.0
O4—C6—H6A	110.2	C17—C16—H16	120.0
O4—C6—H6B	110.2	C18—C17—H17	120.0
C5—C6—H6A	110.2	C16—C17—C18	120.0
C5—C6—H6B	110.2	C16—C17—H17	120.0
H6A—C6—H6B	108.5
O7—S1—N2—S2	168.3 (3)	C2—O2—C3—C4	−179.0 (3)
O8—S1—N2—S2	−63.5 (3)	C3—O2—C2—C1	173.9 (3)
O9—S2—N2—S1	−168.9 (2)	C4—O3—C5—C6	179.8 (3)
O9—S2—C21—F1	−177.1 (3)	C5—O3—C4—C3	−177.4 (3)
O9—S2—C21—F2	−56.1 (3)	C6—O4—C7—C8	−179.6 (3)
O9—S2—C21—F3	65.5 (3)	C7—O4—C6—C5	174.9 (3)
O10—S2—N2—S1	−34.0 (3)	C8—O5—C9—C10	179.3 (3)
O10—S2—C21—F1	60.9 (3)	C9—O5—C8—C7	−177.0 (3)
O10—S2—C21—F2	−178.2 (3)	C10—O6—C11—C12	179.8 (3)
O10—S2—C21—F3	−56.6 (3)	C11—O6—C10—C9	177.5 (3)
N2—S2—C21—F1	−62.1 (3)	C12—O1—C1—C2	−177.4 (3)
N2—S2—C21—F2	58.8 (3)	N1—C13—C14—C19	−87.8 (3)
N2—S2—C21—F3	−179.5 (2)	N1—C13—C14—C15	91.0 (3)
C20—S1—N2—S2	54.1 (3)	C13—C14—C15—C16	−178.8 (2)
C21—S2—N2—S1	80.5 (3)	C18—C19—C14—C13	178.8 (2)
O1—C1—C2—O2	66.6 (3)	C18—C19—C14—C15	0.0
O2—C3—C4—O3	−66.7 (4)	C19—C18—C17—C16	0.0
O3—C5—C6—O4	67.9 (3)	C19—C14—C15—C16	0.0
O4—C7—C8—O5	−63.4 (4)	C14—C15—C16—C17	0.0
O5—C9—C10—O6	66.3 (4)	C15—C16—C17—C18	0.0
O6—C11—C12—O1	−71.0 (3)	C17—C18—C19—C14	0.0
C1—O1—C12—C11	−174.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O1	0.81 (3)	2.10 (3)	2.898 (4)	174 (4)
N1—H1D···O5	0.80 (3)	2.07 (3)	2.874 (4)	175 (4)
N1—H1E···O3	0.81 (3)	2.07 (3)	2.839 (4)	158 (4)