Synthesis and crystal structures of two 1,3-di(alk­yloxy)-2-(methyl­sulfan­yl)imidazolium tetra­fluorido­borates

In both structures, the alk­yloxy and methyl­sulfanyl groups are rotated out of the plane of the respective heterocyclic ring.

Key indicators

Structure: 1

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.037
• wR factor = 0.088
• Data-to-parameter ratio = 14.7

Structure: 2

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in solvent or counterion
• R factor = 0.030
• wR factor = 0.067
• Data-to-parameter ratio = 11.4

checkCIF/PLATON results

No syntax errors found



Datablock: 1


Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4B      ..F3       .       2.61 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.509 Check
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT242_ALERT_2_G Low    MainMol Ueq as Compared to Neighbors of         B1 Check
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O1             110.4 Degree
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O2             110.5 Degree
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          3 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          4 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: 2


Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax < 18) ........       6.08 Note
PLAT244_ALERT_4_C Low    Solvent Ueq as Compared to Neighbors of         B1 Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00413 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4A      ..F2C      .       2.56 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4B      ..F4C      .       2.61 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H18C     ..F3A      .       2.62 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         11 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         10 Report
PLAT128_ALERT_4_G Alternate Setting for Input Space Group  Pc21b        Pca21 Note
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          2 Report
PLAT177_ALERT_4_G The CIF-Embedded .res File Contains DELU Records          1 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          1 Report
PLAT186_ALERT_4_G The CIF-Embedded .res File Contains ISOR Records          1 Report
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  2  )        60% Note
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O1             109.5 Degree
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O2             111.9 Degree
PLAT432_ALERT_2_G Short Inter X...Y Contact  F2C      ..C2               2.94 Ang.
                                             1-x,-1/2+y,1-z  =      2_646 Check
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............        368 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          4 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

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

   0 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
   5 ALERT type 3 Indicator that the structure quality may be low
  11 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

For both structures, data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL2014/6 (Sheldrick, 2015); molecular graphics: XP/SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2020); software used to prepare material for publication: publCIF (Westrip, 2010).

1,3-Dimethoxy-2-(methylsulfanyl)imidazolium tetrafluoridoborate (1)

Crystal data

C6H11N2O2S^+·BF4^−	F(000) = 536
Mr = 262.04	Dx = 1.520 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.1049 (7) Å	Cell parameters from 1882 reflections
b = 11.6979 (10) Å	θ = 4.5–23.4°
c = 12.0810 (12) Å	µ = 0.32 mm^−1
β = 90.069 (9)°	T = 173 K
V = 1145.40 (18) Å^3	Block, colourless
Z = 4	0.20 × 0.14 × 0.12 mm

Data collection

Rigaku Oxford Diffraction Xcalibur, Ruby, Gemini ultra diffractometer	2175 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	1640 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 10.3575 pixels mm^-1	θmax = 25.7°, θmin = 3.4°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2015)	k = −14→14
Tmin = 0.973, Tmax = 1	l = −11→14
8186 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.088	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0305P)^2 + 0.4296P] where P = (Fo^2 + 2Fc^2)/3
2175 reflections	(Δ/σ)max < 0.001
148 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

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	0.41330 (7)	0.47008 (5)	0.72979 (5)	0.03744 (19)
F1	0.08382 (16)	0.25059 (12)	0.80034 (13)	0.0477 (4)
F2	−0.01740 (16)	0.36253 (12)	0.66193 (10)	0.0439 (4)
F3	−0.0285 (2)	0.42160 (11)	0.83926 (11)	0.0516 (4)
F4	−0.18980 (16)	0.27590 (12)	0.78296 (13)	0.0514 (4)
O1	0.46146 (18)	0.22793 (13)	0.61505 (12)	0.0344 (4)
O2	0.45275 (18)	0.38275 (13)	0.97279 (12)	0.0340 (4)
N2	0.4484 (2)	0.30437 (14)	0.88842 (14)	0.0255 (4)
N1	0.4543 (2)	0.23500 (14)	0.72783 (14)	0.0251 (4)
C1	0.4420 (2)	0.33444 (17)	0.78163 (17)	0.0246 (5)
C2	0.4692 (2)	0.14498 (18)	0.79882 (19)	0.0304 (5)
H2	0.4810	0.0667	0.7796	0.036*
C3	0.4638 (2)	0.18919 (18)	0.90157 (19)	0.0301 (5)
H3	0.4696	0.1484	0.9695	0.036*
C5	0.2956 (3)	0.3860 (2)	1.0302 (2)	0.0389 (6)
H5A	0.2067	0.3988	0.9766	0.058*
H5B	0.2965	0.4482	1.0845	0.058*
H5C	0.2775	0.3131	1.0683	0.058*
C6	0.6002 (3)	0.4910 (2)	0.6533 (2)	0.0477 (7)
H6A	0.6951	0.4823	0.7029	0.072*
H6B	0.6007	0.5680	0.6213	0.072*
H6C	0.6069	0.4343	0.5938	0.072*
B1	−0.0377 (3)	0.3266 (2)	0.7711 (2)	0.0276 (6)
C4	0.3017 (3)	0.1968 (2)	0.5703 (2)	0.0471 (7)
H4A	0.2681	0.1226	0.6004	0.071*
H4B	0.3088	0.1917	0.4895	0.071*
H4C	0.2203	0.2549	0.5908	0.071*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0346 (3)	0.0294 (3)	0.0484 (4)	0.0073 (2)	0.0086 (3)	0.0077 (3)
F1	0.0337 (8)	0.0490 (9)	0.0605 (10)	0.0094 (6)	−0.0015 (7)	0.0051 (7)
F2	0.0500 (8)	0.0562 (9)	0.0254 (7)	0.0007 (7)	0.0062 (6)	0.0000 (6)
F3	0.0889 (12)	0.0336 (8)	0.0323 (8)	−0.0033 (7)	0.0035 (7)	−0.0043 (6)
F4	0.0278 (7)	0.0643 (10)	0.0621 (10)	−0.0099 (7)	−0.0001 (7)	0.0120 (8)
O1	0.0272 (8)	0.0512 (10)	0.0247 (9)	−0.0011 (7)	0.0056 (6)	−0.0087 (7)
O2	0.0307 (8)	0.0409 (9)	0.0305 (9)	−0.0101 (7)	0.0022 (7)	−0.0140 (7)
N2	0.0237 (9)	0.0262 (9)	0.0266 (10)	−0.0035 (7)	−0.0003 (7)	−0.0059 (8)
N1	0.0219 (9)	0.0292 (10)	0.0242 (10)	−0.0009 (7)	0.0008 (7)	−0.0048 (8)
C1	0.0183 (10)	0.0277 (11)	0.0276 (12)	0.0007 (9)	0.0019 (9)	−0.0019 (10)
C2	0.0243 (11)	0.0254 (11)	0.0415 (14)	−0.0001 (9)	−0.0022 (10)	0.0010 (10)
C3	0.0277 (11)	0.0289 (12)	0.0337 (14)	−0.0020 (9)	−0.0052 (10)	0.0052 (10)
C5	0.0343 (13)	0.0493 (15)	0.0331 (13)	0.0004 (11)	0.0069 (10)	−0.0069 (11)
C6	0.0413 (15)	0.0406 (14)	0.0613 (18)	0.0012 (12)	0.0150 (13)	0.0150 (13)
B1	0.0253 (13)	0.0294 (13)	0.0282 (14)	−0.0015 (11)	0.0014 (10)	−0.0017 (11)
C4	0.0339 (13)	0.0779 (19)	0.0294 (14)	−0.0056 (13)	−0.0041 (11)	−0.0124 (13)

Geometric parameters (Å, º)

S1—C1	1.722 (2)	N1—C2	1.363 (3)
S1—C6	1.792 (2)	C2—C3	1.346 (3)
F1—B1	1.373 (3)	C2—H2	0.9500
F2—B1	1.394 (3)	C3—H3	0.9500
F3—B1	1.385 (3)	C5—H5A	0.9800
F4—B1	1.376 (3)	C5—H5B	0.9800
O1—N1	1.366 (2)	C5—H5C	0.9800
O1—C4	1.449 (3)	C6—H6A	0.9800
O2—N2	1.372 (2)	C6—H6B	0.9800
O2—C5	1.451 (3)	C6—H6C	0.9800
N2—C1	1.338 (3)	C4—H4A	0.9800
N2—C3	1.362 (3)	C4—H4B	0.9800
N1—C1	1.336 (3)	C4—H4C	0.9800
C1—S1—C6	101.52 (10)	O2—C5—H5C	109.5
N1—O1—C4	110.37 (15)	H5A—C5—H5C	109.5
N2—O2—C5	110.52 (15)	H5B—C5—H5C	109.5
C1—N2—C3	112.08 (17)	S1—C6—H6A	109.5
C1—N2—O2	122.80 (17)	S1—C6—H6B	109.5
C3—N2—O2	124.90 (17)	H6A—C6—H6B	109.5
C1—N1—C2	111.90 (18)	S1—C6—H6C	109.5
C1—N1—O1	122.75 (17)	H6A—C6—H6C	109.5
C2—N1—O1	125.22 (17)	H6B—C6—H6C	109.5
N1—C1—N2	103.73 (17)	F1—B1—F4	109.66 (19)
N1—C1—S1	129.46 (17)	F1—B1—F3	109.20 (19)
N2—C1—S1	126.73 (16)	F4—B1—F3	109.36 (18)
C3—C2—N1	106.29 (19)	F1—B1—F2	110.68 (18)
C3—C2—H2	126.9	F4—B1—F2	109.58 (19)
N1—C2—H2	126.9	F3—B1—F2	108.32 (18)
C2—C3—N2	106.00 (19)	O1—C4—H4A	109.5
C2—C3—H3	127.0	O1—C4—H4B	109.5
N2—C3—H3	127.0	H4A—C4—H4B	109.5
O2—C5—H5A	109.5	O1—C4—H4C	109.5
O2—C5—H5B	109.5	H4A—C4—H4C	109.5
H5A—C5—H5B	109.5	H4B—C4—H4C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···F3^i	0.95	2.26	3.137 (3)	154
C2—H2···F2^i	0.95	2.51	3.361 (3)	150
C3—H3···F2^ii	0.95	2.33	3.207 (3)	153
C4—H4B···F3^iii	0.98	2.61	3.408 (3)	139
C4—H4B···F4^iii	0.98	2.52	3.487 (3)	168
C4—H4C···F2	0.98	2.46	3.418 (3)	167
C5—H5A···F3	0.98	2.54	3.519 (3)	177

Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2; (ii) x+1/2, −y+1/2, z+1/2; (iii) x+1/2, −y+1/2, z−1/2.

1,3-Dibenzyloxy-2-(methylsulfanyl)imidazolium tetrafluoridoborate (2)

Crystal data

C18H19N2O2S^+·BF4^−	F(000) = 856
Mr = 414.22	Dx = 1.445 Mg m^−3
Orthorhombic, Pc21b	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2bc -2c	Cell parameters from 6176 reflections
a = 7.9117 (3) Å	θ = 3.1–28.6°
b = 11.4760 (4) Å	µ = 0.22 mm^−1
c = 20.9659 (7) Å	T = 173 K
V = 1903.59 (12) Å^3	Plate, colourless
Z = 4	0.44 × 0.36 × 0.12 mm

Data collection

Rigaku Oxford Diffraction Xcalibur, Ruby, Gemini ultra diffractometer	3555 independent reflections
Graphite monochromator	3293 reflections with I > 2σ(I)
Detector resolution: 10.3575 pixels mm^-1	Rint = 0.029
ω scans	θmax = 25.7°, θmin = 3.2°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2015)	h = −9→8
Tmin = 0.936, Tmax = 1	k = −13→13
11654 measured reflections	l = −19→25

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.030	H-atom parameters constrained
wR(F^2) = 0.067	w = 1/[σ^2(Fo^2) + (0.031P)^2 + 0.3041P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.007
3555 reflections	Δρmax = 0.18 e Å^−3
311 parameters	Δρmin = −0.22 e Å^−3
368 restraints	Absolute structure: Flack x determined using 1454 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013).
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (3)

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)
B1	0.7773 (4)	0.7700 (3)	0.47458 (15)	0.0309 (7)
F1	0.6678 (2)	0.84120 (18)	0.44219 (10)	0.0588 (6)
F2B	0.719 (2)	0.7454 (15)	0.5332 (6)	0.071 (6)	0.341 (5)
F3B	0.781 (3)	0.6596 (8)	0.4439 (7)	0.072 (5)	0.341 (5)
F4B	0.9356 (13)	0.8091 (14)	0.4735 (12)	0.083 (9)	0.341 (5)
F2C	0.7136 (18)	0.6688 (14)	0.4845 (18)	0.093 (7)	0.238 (4)
F3C	0.9288 (16)	0.7723 (19)	0.4449 (8)	0.060 (6)	0.238 (4)
F4C	0.803 (3)	0.834 (2)	0.5316 (6)	0.089 (6)	0.238 (4)
F2A	0.6947 (13)	0.7094 (11)	0.5212 (5)	0.044 (3)	0.421 (4)
F3A	0.849 (2)	0.6901 (17)	0.4354 (6)	0.126 (8)	0.421 (4)
F4A	0.9031 (14)	0.8315 (12)	0.5042 (8)	0.076 (5)	0.421 (4)
S1	0.33131 (8)	0.61824 (6)	0.53046 (3)	0.02961 (17)
O2	0.3430 (2)	0.66702 (16)	0.38403 (8)	0.0283 (4)
O1	0.2637 (2)	0.87919 (17)	0.57345 (8)	0.0273 (4)
N1	0.2835 (2)	0.85434 (19)	0.50947 (9)	0.0223 (5)
N2	0.3093 (2)	0.75797 (18)	0.42440 (10)	0.0214 (5)
C1	0.3058 (3)	0.7453 (2)	0.48800 (12)	0.0208 (5)
C3	0.2924 (3)	0.8725 (2)	0.40683 (12)	0.0256 (6)
H3	0.2937	0.9028	0.3647	0.031*
C12	0.1490 (3)	0.6677 (2)	0.29313 (12)	0.0261 (6)
C9	0.2992 (3)	1.0534 (3)	0.75895 (14)	0.0350 (7)
H9	0.2491	1.1218	0.7762	0.042*
C10	0.3228 (3)	1.0439 (3)	0.69382 (13)	0.0304 (6)
H10	0.2893	1.1057	0.6665	0.036*
C5	0.3952 (3)	0.9444 (2)	0.66841 (12)	0.0280 (6)
C6	0.4421 (4)	0.8550 (3)	0.70894 (13)	0.0342 (7)
H6	0.4907	0.7860	0.6919	0.041*
C11	0.1862 (3)	0.6160 (3)	0.35716 (12)	0.0314 (6)
H11A	0.0904	0.6312	0.3864	0.038*
H11B	0.1995	0.5305	0.3530	0.038*
C15	0.0978 (4)	0.7695 (3)	0.17451 (14)	0.0389 (7)
H15	0.0811	0.8047	0.1340	0.047*
C17	0.0445 (3)	0.7640 (3)	0.28694 (13)	0.0331 (6)
H17	−0.0103	0.7953	0.3234	0.040*
C2	0.2736 (3)	0.9333 (2)	0.46104 (12)	0.0252 (6)
H2	0.2567	1.0150	0.4649	0.030*
C7	0.4189 (4)	0.8652 (3)	0.77389 (14)	0.0392 (7)
H7	0.4521	0.8034	0.8013	0.047*
C8	0.3482 (4)	0.9641 (3)	0.79913 (14)	0.0369 (7)
H8	0.3329	0.9712	0.8439	0.044*
C4	0.4199 (4)	0.9319 (3)	0.59824 (13)	0.0405 (8)
H4A	0.4396	1.0090	0.5783	0.049*
H4B	0.5183	0.8812	0.5891	0.049*
C13	0.2265 (3)	0.6217 (3)	0.23927 (12)	0.0318 (6)
H13	0.2976	0.5554	0.2429	0.038*
C18	0.1150 (4)	0.5878 (3)	0.55032 (17)	0.0498 (9)
H18A	0.0666	0.6545	0.5731	0.075*
H18B	0.1098	0.5185	0.5775	0.075*
H18C	0.0506	0.5738	0.5111	0.075*
C14	0.2001 (4)	0.6726 (3)	0.18030 (14)	0.0396 (7)
H14	0.2527	0.6406	0.1435	0.047*
C16	0.0199 (4)	0.8148 (3)	0.22780 (14)	0.0389 (7)
H16	−0.0511	0.8812	0.2239	0.047*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
B1	0.0229 (16)	0.040 (2)	0.0298 (17)	0.0004 (14)	−0.0001 (12)	0.0065 (16)
F1	0.0409 (11)	0.0542 (13)	0.0813 (14)	−0.0050 (9)	−0.0231 (9)	0.0296 (11)
F2B	0.102 (13)	0.081 (13)	0.029 (4)	0.002 (9)	0.017 (5)	−0.004 (6)
F3B	0.136 (16)	0.027 (4)	0.052 (7)	−0.007 (7)	−0.004 (8)	−0.014 (4)
F4B	0.025 (4)	0.051 (9)	0.17 (3)	0.002 (4)	0.011 (10)	0.043 (14)
F2C	0.066 (9)	0.037 (10)	0.17 (2)	−0.010 (7)	−0.002 (14)	0.053 (14)
F3C	0.031 (7)	0.087 (16)	0.061 (8)	0.015 (7)	0.020 (5)	−0.001 (8)
F4C	0.092 (12)	0.138 (17)	0.037 (6)	0.040 (11)	−0.013 (7)	−0.024 (8)
F2A	0.039 (3)	0.038 (6)	0.055 (7)	−0.012 (4)	0.007 (4)	0.014 (5)
F3A	0.101 (10)	0.21 (2)	0.071 (6)	0.089 (12)	0.018 (7)	−0.037 (11)
F4A	0.044 (7)	0.073 (8)	0.110 (11)	−0.038 (7)	−0.047 (7)	0.047 (7)
S1	0.0245 (3)	0.0282 (3)	0.0362 (4)	0.0029 (3)	0.0005 (2)	0.0108 (3)
O2	0.0270 (9)	0.0310 (10)	0.0269 (9)	0.0062 (8)	−0.0021 (7)	−0.0098 (8)
O1	0.0244 (9)	0.0357 (11)	0.0217 (9)	−0.0087 (8)	0.0059 (6)	−0.0073 (8)
N1	0.0218 (10)	0.0238 (12)	0.0211 (11)	−0.0014 (9)	0.0033 (8)	−0.0032 (9)
N2	0.0207 (10)	0.0211 (12)	0.0225 (11)	0.0024 (9)	0.0010 (8)	−0.0032 (9)
C1	0.0180 (11)	0.0229 (14)	0.0214 (13)	−0.0012 (10)	0.0001 (9)	0.0016 (11)
C3	0.0226 (12)	0.0271 (14)	0.0271 (13)	−0.0004 (11)	0.0009 (9)	0.0071 (13)
C12	0.0228 (12)	0.0268 (14)	0.0285 (13)	−0.0044 (11)	−0.0056 (10)	−0.0050 (12)
C9	0.0378 (15)	0.0281 (16)	0.0390 (16)	0.0001 (12)	0.0049 (12)	−0.0099 (14)
C10	0.0317 (14)	0.0248 (15)	0.0345 (15)	−0.0033 (12)	−0.0019 (11)	0.0027 (13)
C5	0.0228 (13)	0.0330 (15)	0.0281 (14)	−0.0099 (11)	0.0013 (10)	−0.0051 (12)
C6	0.0286 (14)	0.0287 (16)	0.0454 (17)	0.0007 (12)	−0.0035 (11)	−0.0099 (14)
C11	0.0370 (14)	0.0239 (13)	0.0332 (14)	−0.0047 (13)	−0.0049 (10)	−0.0033 (15)
C15	0.0431 (17)	0.0391 (18)	0.0345 (16)	−0.0097 (14)	−0.0149 (13)	0.0054 (14)
C17	0.0259 (13)	0.0358 (17)	0.0376 (16)	0.0009 (12)	−0.0036 (11)	−0.0079 (14)
C2	0.0213 (13)	0.0197 (13)	0.0346 (15)	−0.0018 (10)	0.0032 (10)	0.0007 (12)
C7	0.0406 (17)	0.0327 (17)	0.0443 (17)	−0.0056 (13)	−0.0148 (12)	0.0075 (16)
C8	0.0434 (18)	0.0428 (18)	0.0244 (15)	−0.0114 (14)	−0.0016 (12)	−0.0032 (13)
C4	0.0281 (14)	0.061 (2)	0.0327 (15)	−0.0200 (14)	0.0055 (12)	−0.0142 (15)
C13	0.0338 (14)	0.0274 (14)	0.0341 (15)	0.0017 (13)	−0.0056 (10)	−0.0108 (15)
C18	0.0327 (16)	0.042 (2)	0.074 (2)	0.0042 (14)	0.0209 (15)	0.0267 (17)
C14	0.0437 (17)	0.0448 (18)	0.0302 (15)	−0.0041 (15)	−0.0035 (13)	−0.0108 (14)
C16	0.0351 (16)	0.0323 (17)	0.049 (2)	0.0020 (13)	−0.0142 (13)	0.0023 (14)

Geometric parameters (Å, º)

B1—F2C	1.283 (11)	C9—H9	0.9500
B1—F4B	1.330 (10)	C10—C5	1.384 (4)
B1—F2B	1.342 (11)	C10—H10	0.9500
B1—F3C	1.350 (11)	C5—C6	1.383 (4)
B1—F3A	1.355 (10)	C5—C4	1.491 (4)
B1—F2A	1.367 (8)	C6—C7	1.379 (4)
B1—F4A	1.369 (9)	C6—H6	0.9500
B1—F1	1.371 (4)	C11—H11A	0.9900
B1—F4C	1.414 (12)	C11—H11B	0.9900
B1—F3B	1.422 (9)	C15—C16	1.378 (4)
S1—C1	1.721 (3)	C15—C14	1.381 (5)
S1—C18	1.795 (3)	C15—H15	0.9500
O2—N2	1.370 (3)	C17—C16	1.384 (4)
O2—C11	1.483 (3)	C17—H17	0.9500
O1—N1	1.380 (3)	C2—H2	0.9500
O1—C4	1.471 (3)	C7—C8	1.372 (5)
N1—C1	1.341 (3)	C7—H7	0.9500
N1—C2	1.363 (3)	C8—H8	0.9500
N2—C1	1.342 (3)	C4—H4A	0.9900
N2—C3	1.372 (3)	C4—H4B	0.9900
C3—C2	1.342 (4)	C13—C14	1.383 (4)
C3—H3	0.9500	C13—H13	0.9500
C12—C17	1.386 (4)	C18—H18A	0.9800
C12—C13	1.389 (4)	C18—H18B	0.9800
C12—C11	1.497 (4)	C18—H18C	0.9800
C9—C8	1.382 (4)	C14—H14	0.9500
C9—C10	1.383 (4)	C16—H16	0.9500
F4B—B1—F2B	114.1 (10)	C7—C6—C5	120.6 (3)
F2C—B1—F3C	116.1 (11)	C7—C6—H6	119.7
F3A—B1—F2A	106.7 (8)	C5—C6—H6	119.7
F3A—B1—F4A	108.8 (8)	O2—C11—C12	110.4 (2)
F2A—B1—F4A	106.6 (7)	O2—C11—H11A	109.6
F2C—B1—F1	111.8 (7)	C12—C11—H11A	109.6
F4B—B1—F1	112.7 (7)	O2—C11—H11B	109.6
F2B—B1—F1	111.3 (8)	C12—C11—H11B	109.6
F3C—B1—F1	108.8 (8)	H11A—C11—H11B	108.1
F3A—B1—F1	111.5 (6)	C16—C15—C14	119.7 (3)
F2A—B1—F1	110.8 (5)	C16—C15—H15	120.2
F4A—B1—F1	112.2 (6)	C14—C15—H15	120.2
F2C—B1—F4C	112.7 (11)	C16—C17—C12	120.3 (3)
F3C—B1—F4C	104.6 (10)	C16—C17—H17	119.9
F1—B1—F4C	101.7 (6)	C12—C17—H17	119.9
F4B—B1—F3B	105.9 (8)	C3—C2—N1	106.2 (2)
F2B—B1—F3B	103.5 (8)	C3—C2—H2	126.9
F1—B1—F3B	108.6 (7)	N1—C2—H2	126.9
C1—S1—C18	99.97 (13)	C8—C7—C6	120.3 (3)
N2—O2—C11	111.87 (18)	C8—C7—H7	119.8
N1—O1—C4	109.43 (17)	C6—C7—H7	119.8
C1—N1—C2	112.2 (2)	C7—C8—C9	119.5 (3)
C1—N1—O1	122.3 (2)	C7—C8—H8	120.2
C2—N1—O1	125.5 (2)	C9—C8—H8	120.2
C1—N2—O2	122.4 (2)	O1—C4—C5	106.1 (2)
C1—N2—C3	111.6 (2)	O1—C4—H4A	110.5
O2—N2—C3	125.7 (2)	C5—C4—H4A	110.5
N1—C1—N2	103.6 (2)	O1—C4—H4B	110.5
N1—C1—S1	129.23 (19)	C5—C4—H4B	110.5
N2—C1—S1	127.1 (2)	H4A—C4—H4B	108.7
C2—C3—N2	106.4 (2)	C14—C13—C12	120.0 (3)
C2—C3—H3	126.8	C14—C13—H13	120.0
N2—C3—H3	126.8	C12—C13—H13	120.0
C17—C12—C13	119.3 (3)	S1—C18—H18A	109.5
C17—C12—C11	121.2 (2)	S1—C18—H18B	109.5
C13—C12—C11	119.4 (2)	H18A—C18—H18B	109.5
C8—C9—C10	120.4 (3)	S1—C18—H18C	109.5
C8—C9—H9	119.8	H18A—C18—H18C	109.5
C10—C9—H9	119.8	H18B—C18—H18C	109.5
C9—C10—C5	120.1 (3)	C15—C14—C13	120.5 (3)
C9—C10—H10	120.0	C15—C14—H14	119.8
C5—C10—H10	120.0	C13—C14—H14	119.8
C6—C5—C10	119.1 (2)	C15—C16—C17	120.3 (3)
C6—C5—C4	120.0 (3)	C15—C16—H16	119.9
C10—C5—C4	120.9 (3)	C17—C16—H16	119.9
N1—O1—C4—C5	−174.2 (2)	N2—O2—C11—C12	95.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···F2A^i	0.95	2.28	3.200 (13)	162
C2—H2···F3B^i	0.95	2.55	3.302 (14)	136
C2—H2···F2C^i	0.95	2.07	2.936 (10)	150
C4—H4B···F2B	0.99	2.52	3.472 (17)	162
C4—H4A···F3B^i	0.99	2.50	3.183 (13)	126
C4—H4A···F2C^i	0.99	2.56	3.39 (3)	141
C4—H4B···F4C	0.99	2.61	3.522 (19)	153
C8—H8···F1^ii	0.95	2.54	3.317 (4)	139
C10—H10···F3B^i	0.95	2.46	3.282 (12)	145
C11—H11A···F3A^iii	0.99	2.27	3.247 (13)	167
C11—H11A···F3C^iii	0.99	2.40	3.279 (15)	148
C18—H18C···F3A^iii	0.98	2.62	3.409 (14)	138

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