The title quaternary ammonium salt, C18H24NS2+·Cl-, was reported several decades ago, but its structure was not determined at the time. The crystal structure displays extensive hydrogen bonding, linking cations and anions into infinite chains. There are two cations and two anions in the asymmetric unit.
Supporting information
CCDC reference: 255882
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.004 Å
- R factor = 0.048
- wR factor = 0.127
- Data-to-parameter ratio = 21.5
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT113_ALERT_2_A ADDSYM Suggests Possible Pseudo/New Spacegroup . Pccn
| Author Response: Although the data set can be solved in the suggested
space group, the structure solution in P c c n includes
3090 data rejected, 1658 systematic absence violation, a final R1
= 0.1727 wR2 = 0.5786 and an average C-C bond precision of
0.014 Angstrom. Additionally, the data E-stat, 0.789, suggests a
noncentrosymmetric space group and there are no correlation matrix
elements larger than 0.5 in the reported space space group,
P 21 21 2.
|
Alert level B
PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry ..... 100 PerFit
| Author Response: Please see response to suggestion of P c c n
spacegroup.
|
Alert level C
STRVA01_ALERT_4_C Flack test results are ambiguous.
From the CIF: _refine_ls_abs_structure_Flack 0.550
From the CIF: _refine_ls_abs_structure_Flack_su 0.060
PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... 0.55
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.08
| Author Response: No obvious twinning was observed by polarized
microscopy. No remaining significant peaks in the difference map.
|
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 28.30
From the CIF: _reflns_number_total 8603
Count of symmetry unique reflns 5191
Completeness (_total/calc) 165.73%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 3412
Fraction of Friedel pairs measured 0.657
Are heavy atom types Z>Si present yes
1 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
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
0 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2002); cell refinement: SHELXTL (Sheldrick, 2001); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
1-Benzylsulfanyl-2-(benzylsulfanylmethyl)propanaminium chloride
top
Crystal data top
C18H24NS2+·Cl− | F(000) = 1504 |
Mr = 353.95 | Dx = 1.269 Mg m−3 |
Orthorhombic, P21212 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2 2ab | Cell parameters from 1007 reflections |
a = 16.396 (4) Å | θ = 3.2–27.8° |
b = 31.633 (8) Å | µ = 0.43 mm−1 |
c = 7.1438 (19) Å | T = 120 K |
V = 3705.1 (17) Å3 | Needle, yellow |
Z = 8 | 0.36 × 0.04 × 0.04 mm |
Data collection top
Bruker SMART APEX diffractometer | 8603 independent reflections |
Radiation source: fine-focus sealed tube | 8297 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
Detector resolution: 836.6 pixels mm-1 | θmax = 28.3°, θmin = 1.8° |
ω scans | h = −20→21 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | k = −40→41 |
Tmin = 0.861, Tmax = 0.983 | l = −9→9 |
41652 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.127 | w = 1/[σ2(Fo2) + (0.0831P)2 + 1.3761P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
8603 reflections | Δρmax = 0.50 e Å−3 |
400 parameters | Δρmin = −0.24 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 3633 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.55 (6) |
Special details top
Experimental. Data collection is performed with four batch runs at φ = 0.00 ° (600 frames),
at φ = 90.00 ° (600 frames), at φ = 180 ° (600 frames) and at φ = 270 °
(600 frames). Frame width = 0.30 \& in ω. Data is merged, corrected for
decay, and treated with multi-scan absorption corrections. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | 0.91050 (4) | 0.448773 (18) | 0.52541 (9) | 0.02306 (14) | |
Cl2 | 0.08552 (3) | 0.440842 (18) | 1.02930 (9) | 0.02197 (13) | |
N1 | 0.89336 (12) | 0.46171 (6) | 0.0836 (3) | 0.0225 (4) | |
H1B | 0.9084 | 0.4884 | 0.0514 | 0.034* | |
H1C | 0.9231 | 0.4428 | 0.0164 | 0.034* | |
H1D | 0.9025 | 0.4577 | 0.2079 | 0.034* | |
N2 | 0.10306 (12) | 0.45370 (7) | 0.5858 (3) | 0.0230 (4) | |
H2B | 0.0881 | 0.4804 | 0.5538 | 0.034* | |
H2C | 0.0939 | 0.4496 | 0.7102 | 0.034* | |
H2D | 0.0732 | 0.4348 | 0.5186 | 0.034* | |
S1 | 0.88438 (4) | 0.36459 (2) | −0.04757 (9) | 0.02450 (14) | |
S2 | 0.64440 (4) | 0.46346 (2) | 0.32759 (11) | 0.02734 (16) | |
S3 | 0.35138 (4) | 0.45585 (2) | 0.82493 (11) | 0.02917 (17) | |
S4 | 0.10950 (5) | 0.35472 (2) | 0.47148 (9) | 0.02860 (16) | |
C1 | 0.87375 (14) | 0.32030 (8) | 0.4552 (4) | 0.0222 (5) | |
H1A | 0.8736 | 0.3475 | 0.5115 | 0.027* | |
C2 | 0.84365 (16) | 0.28587 (9) | 0.5544 (4) | 0.0270 (5) | |
H2A | 0.8236 | 0.2897 | 0.6780 | 0.032* | |
C3 | 0.84272 (17) | 0.24640 (9) | 0.4744 (4) | 0.0306 (6) | |
H3A | 0.8215 | 0.2230 | 0.5416 | 0.037* | |
C4 | 0.8730 (2) | 0.24100 (9) | 0.2947 (4) | 0.0337 (7) | |
H4A | 0.8724 | 0.2137 | 0.2390 | 0.040* | |
C5 | 0.90426 (18) | 0.27505 (8) | 0.1954 (4) | 0.0283 (6) | |
H5A | 0.9258 | 0.2709 | 0.0733 | 0.034* | |
C6 | 0.90402 (15) | 0.31544 (8) | 0.2752 (4) | 0.0199 (5) | |
C7 | 0.93728 (16) | 0.35285 (8) | 0.1707 (4) | 0.0234 (5) | |
H7A | 0.9955 | 0.3476 | 0.1426 | 0.028* | |
H7B | 0.9343 | 0.3780 | 0.2528 | 0.028* | |
C8 | 0.67372 (15) | 0.36401 (8) | 0.5734 (3) | 0.0204 (5) | |
H8A | 0.7233 | 0.3624 | 0.5048 | 0.025* | |
C9 | 0.63650 (17) | 0.32728 (9) | 0.6322 (4) | 0.0250 (5) | |
H9A | 0.6601 | 0.3007 | 0.6032 | 0.030* | |
C10 | 0.56450 (17) | 0.32921 (9) | 0.7340 (4) | 0.0300 (6) | |
H10A | 0.5390 | 0.3040 | 0.7761 | 0.036* | |
C11 | 0.53010 (16) | 0.36805 (10) | 0.7736 (4) | 0.0272 (6) | |
H11A | 0.4806 | 0.3694 | 0.8424 | 0.033* | |
C12 | 0.56711 (15) | 0.40491 (9) | 0.7139 (4) | 0.0237 (5) | |
H12A | 0.5428 | 0.4314 | 0.7417 | 0.028* | |
C13 | 0.64002 (15) | 0.40338 (8) | 0.6128 (3) | 0.0192 (5) | |
C14 | 0.68167 (15) | 0.44312 (8) | 0.5504 (4) | 0.0249 (5) | |
H14A | 0.7409 | 0.4376 | 0.5394 | 0.030* | |
H14B | 0.6740 | 0.4651 | 0.6476 | 0.030* | |
C15 | 0.78168 (15) | 0.37539 (8) | 0.0342 (4) | 0.0210 (5) | |
H15A | 0.7448 | 0.3755 | −0.0755 | 0.025* | |
H15B | 0.7645 | 0.3518 | 0.1165 | 0.025* | |
C16 | 0.67683 (15) | 0.42253 (8) | 0.1673 (4) | 0.0233 (5) | |
H16A | 0.6541 | 0.3953 | 0.2112 | 0.028* | |
H16B | 0.6525 | 0.4285 | 0.0433 | 0.028* | |
C17 | 0.76945 (15) | 0.41703 (8) | 0.1412 (4) | 0.0190 (5) | |
H17A | 0.7954 | 0.4143 | 0.2674 | 0.023* | |
C18 | 0.80510 (14) | 0.45564 (8) | 0.0428 (4) | 0.0221 (5) | |
H18A | 0.7976 | 0.4525 | −0.0940 | 0.027* | |
H18B | 0.7748 | 0.4811 | 0.0829 | 0.027* | |
C19 | 0.43584 (15) | 0.40176 (8) | 1.2149 (4) | 0.0225 (5) | |
H19A | 0.4564 | 0.4292 | 1.2411 | 0.027* | |
C20 | 0.47821 (16) | 0.36663 (10) | 1.2771 (4) | 0.0293 (6) | |
H20A | 0.5269 | 0.3701 | 1.3475 | 0.035* | |
C21 | 0.44989 (17) | 0.32639 (10) | 1.2371 (4) | 0.0295 (6) | |
H21A | 0.4794 | 0.3023 | 1.2786 | 0.035* | |
C22 | 0.37838 (18) | 0.32148 (9) | 1.1365 (4) | 0.0272 (6) | |
H22A | 0.3586 | 0.2939 | 1.1089 | 0.033* | |
C23 | 0.33533 (15) | 0.35683 (8) | 1.0756 (3) | 0.0201 (5) | |
H23A | 0.2862 | 0.3532 | 1.0069 | 0.024* | |
C24 | 0.36342 (15) | 0.39745 (8) | 1.1142 (3) | 0.0188 (5) | |
C25 | 0.31687 (16) | 0.43547 (8) | 1.0507 (4) | 0.0251 (5) | |
H25A | 0.3224 | 0.4580 | 1.1460 | 0.030* | |
H25B | 0.2583 | 0.4281 | 1.0414 | 0.030* | |
C26 | 0.13763 (15) | 0.31087 (8) | 0.9772 (4) | 0.0233 (5) | |
H26A | 0.1325 | 0.3376 | 1.0369 | 0.028* | |
C27 | 0.17436 (16) | 0.27758 (9) | 1.0724 (4) | 0.0269 (6) | |
H27A | 0.1932 | 0.2814 | 1.1970 | 0.032* | |
C28 | 0.18329 (18) | 0.23893 (9) | 0.9853 (4) | 0.0291 (6) | |
H28A | 0.2095 | 0.2163 | 1.0486 | 0.035* | |
C29 | 0.1538 (2) | 0.23324 (9) | 0.8039 (4) | 0.0352 (7) | |
H29A | 0.1595 | 0.2066 | 0.7441 | 0.042* | |
C30 | 0.11637 (18) | 0.26619 (8) | 0.7111 (4) | 0.0291 (6) | |
H30A | 0.0959 | 0.2619 | 0.5881 | 0.035* | |
C31 | 0.10829 (15) | 0.30573 (8) | 0.7961 (4) | 0.0220 (5) | |
C32 | 0.06632 (15) | 0.34166 (8) | 0.6998 (4) | 0.0240 (5) | |
H32A | 0.0693 | 0.3670 | 0.7811 | 0.029* | |
H32B | 0.0080 | 0.3344 | 0.6836 | 0.029* | |
C33 | 0.31999 (15) | 0.41423 (9) | 0.6660 (4) | 0.0245 (5) | |
H33A | 0.3441 | 0.4200 | 0.5416 | 0.029* | |
H33B | 0.3432 | 0.3872 | 0.7112 | 0.029* | |
C34 | 0.21346 (16) | 0.36724 (8) | 0.5329 (4) | 0.0257 (5) | |
H34A | 0.2354 | 0.3436 | 0.6086 | 0.031* | |
H34B | 0.2458 | 0.3685 | 0.4160 | 0.031* | |
C35 | 0.22768 (15) | 0.40845 (8) | 0.6414 (3) | 0.0187 (5) | |
H35A | 0.2023 | 0.4056 | 0.7681 | 0.022* | |
C36 | 0.19134 (15) | 0.44757 (8) | 0.5449 (4) | 0.0241 (5) | |
H36A | 0.2217 | 0.4730 | 0.5863 | 0.029* | |
H36B | 0.1987 | 0.4448 | 0.4080 | 0.029* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0204 (3) | 0.0199 (3) | 0.0289 (3) | −0.0006 (2) | −0.0028 (2) | −0.0028 (2) |
Cl2 | 0.0196 (3) | 0.0176 (3) | 0.0287 (3) | −0.0001 (2) | 0.0035 (2) | −0.0018 (2) |
N1 | 0.0193 (10) | 0.0168 (10) | 0.0314 (11) | −0.0022 (8) | 0.0037 (9) | 0.0044 (9) |
N2 | 0.0189 (10) | 0.0197 (10) | 0.0303 (11) | 0.0016 (8) | −0.0014 (9) | 0.0032 (9) |
S1 | 0.0349 (3) | 0.0227 (3) | 0.0160 (3) | −0.0001 (2) | 0.0046 (3) | −0.0024 (2) |
S2 | 0.0215 (3) | 0.0225 (3) | 0.0380 (4) | 0.0023 (2) | 0.0050 (3) | 0.0065 (3) |
S3 | 0.0223 (3) | 0.0232 (3) | 0.0419 (4) | −0.0007 (3) | −0.0021 (3) | 0.0107 (3) |
S4 | 0.0414 (4) | 0.0253 (3) | 0.0191 (3) | 0.0055 (3) | −0.0088 (3) | −0.0041 (2) |
C1 | 0.0178 (11) | 0.0242 (12) | 0.0247 (13) | 0.0034 (9) | −0.0040 (10) | −0.0065 (10) |
C2 | 0.0248 (13) | 0.0380 (14) | 0.0183 (12) | 0.0035 (11) | −0.0030 (11) | 0.0000 (11) |
C3 | 0.0337 (14) | 0.0296 (13) | 0.0286 (15) | −0.0003 (11) | −0.0066 (12) | 0.0099 (12) |
C4 | 0.0531 (19) | 0.0189 (12) | 0.0290 (14) | 0.0045 (12) | −0.0025 (14) | −0.0038 (11) |
C5 | 0.0396 (15) | 0.0225 (12) | 0.0229 (12) | 0.0072 (11) | 0.0021 (12) | −0.0043 (10) |
C6 | 0.0163 (10) | 0.0210 (11) | 0.0224 (12) | 0.0047 (9) | −0.0024 (9) | −0.0004 (9) |
C7 | 0.0211 (12) | 0.0253 (12) | 0.0238 (12) | 0.0005 (10) | −0.0002 (10) | 0.0003 (10) |
C8 | 0.0180 (11) | 0.0293 (13) | 0.0139 (10) | 0.0030 (10) | −0.0019 (9) | −0.0008 (10) |
C9 | 0.0272 (13) | 0.0288 (13) | 0.0191 (12) | 0.0046 (11) | −0.0061 (10) | 0.0014 (10) |
C10 | 0.0295 (14) | 0.0345 (15) | 0.0261 (14) | −0.0053 (11) | −0.0040 (11) | 0.0126 (12) |
C11 | 0.0187 (12) | 0.0463 (16) | 0.0166 (12) | 0.0001 (11) | 0.0014 (10) | 0.0057 (11) |
C12 | 0.0195 (12) | 0.0342 (14) | 0.0173 (12) | 0.0043 (10) | −0.0022 (10) | −0.0044 (10) |
C13 | 0.0159 (11) | 0.0255 (12) | 0.0161 (11) | 0.0009 (9) | −0.0032 (9) | −0.0055 (9) |
C14 | 0.0215 (11) | 0.0267 (13) | 0.0265 (13) | −0.0021 (10) | 0.0015 (11) | −0.0088 (11) |
C15 | 0.0229 (11) | 0.0220 (11) | 0.0180 (11) | −0.0045 (9) | −0.0035 (10) | 0.0014 (10) |
C16 | 0.0200 (11) | 0.0280 (13) | 0.0218 (12) | −0.0034 (10) | −0.0015 (10) | 0.0033 (10) |
C17 | 0.0192 (11) | 0.0211 (12) | 0.0167 (11) | −0.0011 (9) | −0.0036 (9) | 0.0021 (9) |
C18 | 0.0207 (11) | 0.0182 (11) | 0.0273 (13) | −0.0020 (9) | −0.0009 (10) | 0.0025 (10) |
C19 | 0.0197 (11) | 0.0268 (13) | 0.0211 (12) | −0.0065 (10) | −0.0016 (10) | −0.0039 (10) |
C20 | 0.0172 (11) | 0.0490 (17) | 0.0216 (13) | −0.0025 (12) | −0.0018 (10) | 0.0074 (12) |
C21 | 0.0278 (13) | 0.0371 (15) | 0.0236 (14) | 0.0062 (12) | 0.0030 (11) | 0.0128 (12) |
C22 | 0.0342 (14) | 0.0257 (13) | 0.0216 (12) | −0.0002 (11) | 0.0049 (11) | 0.0039 (10) |
C23 | 0.0200 (11) | 0.0265 (12) | 0.0138 (10) | −0.0051 (9) | −0.0016 (9) | −0.0005 (9) |
C24 | 0.0177 (11) | 0.0266 (12) | 0.0120 (10) | −0.0012 (9) | 0.0037 (9) | −0.0013 (9) |
C25 | 0.0213 (11) | 0.0244 (12) | 0.0296 (14) | 0.0057 (10) | −0.0004 (11) | −0.0039 (11) |
C26 | 0.0181 (11) | 0.0282 (12) | 0.0237 (13) | −0.0021 (9) | 0.0022 (10) | −0.0078 (10) |
C27 | 0.0264 (13) | 0.0356 (14) | 0.0187 (12) | −0.0035 (11) | −0.0008 (10) | −0.0033 (11) |
C28 | 0.0382 (14) | 0.0257 (13) | 0.0233 (13) | −0.0010 (11) | 0.0052 (12) | 0.0045 (11) |
C29 | 0.0579 (19) | 0.0206 (13) | 0.0271 (14) | −0.0027 (13) | 0.0045 (14) | −0.0039 (11) |
C30 | 0.0430 (16) | 0.0233 (13) | 0.0209 (12) | −0.0031 (12) | −0.0049 (12) | −0.0043 (10) |
C31 | 0.0181 (11) | 0.0217 (12) | 0.0262 (13) | −0.0043 (9) | 0.0028 (10) | −0.0025 (10) |
C32 | 0.0195 (12) | 0.0260 (13) | 0.0265 (13) | 0.0001 (10) | −0.0003 (10) | −0.0069 (11) |
C33 | 0.0208 (12) | 0.0303 (13) | 0.0223 (13) | 0.0049 (10) | 0.0036 (10) | 0.0090 (11) |
C34 | 0.0307 (13) | 0.0248 (12) | 0.0215 (12) | 0.0097 (10) | 0.0073 (11) | 0.0023 (11) |
C35 | 0.0192 (11) | 0.0212 (11) | 0.0157 (11) | 0.0063 (9) | 0.0042 (9) | 0.0040 (9) |
C36 | 0.0207 (11) | 0.0245 (12) | 0.0271 (13) | 0.0042 (9) | 0.0040 (11) | 0.0055 (11) |
Geometric parameters (Å, º) top
N1—C18 | 1.488 (3) | C15—H15B | 0.9900 |
N1—H1B | 0.9100 | C16—C17 | 1.540 (3) |
N1—H1C | 0.9100 | C16—H16A | 0.9900 |
N1—H1D | 0.9100 | C16—H16B | 0.9900 |
N2—C36 | 1.489 (3) | C17—C18 | 1.526 (3) |
N2—H2B | 0.9100 | C17—H17A | 1.0000 |
N2—H2C | 0.9100 | C18—H18A | 0.9900 |
N2—H2D | 0.9100 | C18—H18B | 0.9900 |
S1—C15 | 1.815 (3) | C19—C20 | 1.384 (4) |
S1—C7 | 1.822 (3) | C19—C24 | 1.395 (3) |
S2—C16 | 1.809 (3) | C19—H19A | 0.9500 |
S2—C14 | 1.822 (3) | C20—C21 | 1.385 (4) |
S3—C33 | 1.813 (3) | C20—H20A | 0.9500 |
S3—C25 | 1.827 (3) | C21—C22 | 1.384 (4) |
S4—C34 | 1.804 (3) | C21—H21A | 0.9500 |
S4—C32 | 1.826 (3) | C22—C23 | 1.392 (4) |
C1—C6 | 1.387 (4) | C22—H22A | 0.9500 |
C1—C2 | 1.390 (4) | C23—C24 | 1.393 (3) |
C1—H1A | 0.9500 | C23—H23A | 0.9500 |
C2—C3 | 1.373 (4) | C24—C25 | 1.495 (3) |
C2—H2A | 0.9500 | C25—H25A | 0.9900 |
C3—C4 | 1.387 (4) | C25—H25B | 0.9900 |
C3—H3A | 0.9500 | C26—C31 | 1.390 (4) |
C4—C5 | 1.387 (4) | C26—C27 | 1.391 (4) |
C4—H4A | 0.9500 | C26—H26A | 0.9500 |
C5—C6 | 1.399 (3) | C27—C28 | 1.380 (4) |
C5—H5A | 0.9500 | C27—H27A | 0.9500 |
C6—C7 | 1.502 (3) | C28—C29 | 1.394 (4) |
C7—H7A | 0.9900 | C28—H28A | 0.9500 |
C7—H7B | 0.9900 | C29—C30 | 1.379 (4) |
C8—C9 | 1.378 (4) | C29—H29A | 0.9500 |
C8—C13 | 1.391 (3) | C30—C31 | 1.397 (4) |
C8—H8A | 0.9500 | C30—H30A | 0.9500 |
C9—C10 | 1.388 (4) | C31—C32 | 1.496 (4) |
C9—H9A | 0.9500 | C32—H32A | 0.9900 |
C10—C11 | 1.381 (4) | C32—H32B | 0.9900 |
C10—H10A | 0.9500 | C33—C35 | 1.535 (3) |
C11—C12 | 1.382 (4) | C33—H33A | 0.9900 |
C11—H11A | 0.9500 | C33—H33B | 0.9900 |
C12—C13 | 1.397 (3) | C34—C35 | 1.535 (4) |
C12—H12A | 0.9500 | C34—H34A | 0.9900 |
C13—C14 | 1.499 (4) | C34—H34B | 0.9900 |
C14—H14A | 0.9900 | C35—C36 | 1.536 (3) |
C14—H14B | 0.9900 | C35—H35A | 1.0000 |
C15—C17 | 1.536 (3) | C36—H36A | 0.9900 |
C15—H15A | 0.9900 | C36—H36B | 0.9900 |
| | | |
C18—N1—H1B | 109.5 | C15—C17—H17A | 108.7 |
C18—N1—H1C | 109.5 | C16—C17—H17A | 108.7 |
H1B—N1—H1C | 109.5 | N1—C18—C17 | 112.7 (2) |
C18—N1—H1D | 109.5 | N1—C18—H18A | 109.1 |
H1B—N1—H1D | 109.5 | C17—C18—H18A | 109.1 |
H1C—N1—H1D | 109.5 | N1—C18—H18B | 109.1 |
C36—N2—H2B | 109.5 | C17—C18—H18B | 109.1 |
C36—N2—H2C | 109.5 | H18A—C18—H18B | 107.8 |
H2B—N2—H2C | 109.5 | C20—C19—C24 | 121.0 (2) |
C36—N2—H2D | 109.5 | C20—C19—H19A | 119.5 |
H2B—N2—H2D | 109.5 | C24—C19—H19A | 119.5 |
H2C—N2—H2D | 109.5 | C21—C20—C19 | 120.2 (3) |
C15—S1—C7 | 101.81 (12) | C21—C20—H20A | 119.9 |
C16—S2—C14 | 101.64 (12) | C19—C20—H20A | 119.9 |
C33—S3—C25 | 102.05 (12) | C22—C21—C20 | 119.6 (3) |
C34—S4—C32 | 101.47 (12) | C22—C21—H21A | 120.2 |
C6—C1—C2 | 120.8 (2) | C20—C21—H21A | 120.2 |
C6—C1—H1A | 119.6 | C21—C22—C23 | 120.1 (3) |
C2—C1—H1A | 119.6 | C21—C22—H22A | 119.9 |
C3—C2—C1 | 120.3 (3) | C23—C22—H22A | 119.9 |
C3—C2—H2A | 119.9 | C22—C23—C24 | 120.8 (2) |
C1—C2—H2A | 119.9 | C22—C23—H23A | 119.6 |
C2—C3—C4 | 119.6 (3) | C24—C23—H23A | 119.6 |
C2—C3—H3A | 120.2 | C23—C24—C19 | 118.3 (2) |
C4—C3—H3A | 120.2 | C23—C24—C25 | 120.9 (2) |
C3—C4—C5 | 120.6 (3) | C19—C24—C25 | 120.8 (2) |
C3—C4—H4A | 119.7 | C24—C25—S3 | 113.18 (18) |
C5—C4—H4A | 119.7 | C24—C25—H25A | 108.9 |
C4—C5—C6 | 120.0 (3) | S3—C25—H25A | 108.9 |
C4—C5—H5A | 120.0 | C24—C25—H25B | 108.9 |
C6—C5—H5A | 120.0 | S3—C25—H25B | 108.9 |
C1—C6—C5 | 118.7 (2) | H25A—C25—H25B | 107.8 |
C1—C6—C7 | 120.3 (2) | C31—C26—C27 | 121.1 (2) |
C5—C6—C7 | 121.1 (2) | C31—C26—H26A | 119.4 |
C6—C7—S1 | 114.41 (18) | C27—C26—H26A | 119.4 |
C6—C7—H7A | 108.7 | C28—C27—C26 | 119.7 (3) |
S1—C7—H7A | 108.7 | C28—C27—H27A | 120.1 |
C6—C7—H7B | 108.7 | C26—C27—H27A | 120.1 |
S1—C7—H7B | 108.7 | C27—C28—C29 | 119.8 (3) |
H7A—C7—H7B | 107.6 | C27—C28—H28A | 120.1 |
C9—C8—C13 | 121.1 (2) | C29—C28—H28A | 120.1 |
C9—C8—H8A | 119.4 | C30—C29—C28 | 120.2 (3) |
C13—C8—H8A | 119.4 | C30—C29—H29A | 119.9 |
C8—C9—C10 | 120.0 (3) | C28—C29—H29A | 119.9 |
C8—C9—H9A | 120.0 | C29—C30—C31 | 120.6 (3) |
C10—C9—H9A | 120.0 | C29—C30—H30A | 119.7 |
C11—C10—C9 | 119.6 (3) | C31—C30—H30A | 119.7 |
C11—C10—H10A | 120.2 | C26—C31—C30 | 118.5 (3) |
C9—C10—H10A | 120.2 | C26—C31—C32 | 119.9 (2) |
C12—C11—C10 | 120.5 (2) | C30—C31—C32 | 121.6 (2) |
C12—C11—H11A | 119.7 | C31—C32—S4 | 113.85 (18) |
C10—C11—H11A | 119.7 | C31—C32—H32A | 108.8 |
C11—C12—C13 | 120.4 (3) | S4—C32—H32A | 108.8 |
C11—C12—H12A | 119.8 | C31—C32—H32B | 108.8 |
C13—C12—H12A | 119.8 | S4—C32—H32B | 108.8 |
C8—C13—C12 | 118.4 (2) | H32A—C32—H32B | 107.7 |
C8—C13—C14 | 120.6 (2) | C35—C33—S3 | 116.00 (18) |
C12—C13—C14 | 121.0 (2) | C35—C33—H33A | 108.3 |
C13—C14—S2 | 113.79 (18) | S3—C33—H33A | 108.3 |
C13—C14—H14A | 108.8 | C35—C33—H33B | 108.3 |
S2—C14—H14A | 108.8 | S3—C33—H33B | 108.3 |
C13—C14—H14B | 108.8 | H33A—C33—H33B | 107.4 |
S2—C14—H14B | 108.8 | C35—C34—S4 | 116.93 (17) |
H14A—C14—H14B | 107.7 | C35—C34—H34A | 108.1 |
C17—C15—S1 | 116.28 (17) | S4—C34—H34A | 108.1 |
C17—C15—H15A | 108.2 | C35—C34—H34B | 108.1 |
S1—C15—H15A | 108.2 | S4—C34—H34B | 108.1 |
C17—C15—H15B | 108.2 | H34A—C34—H34B | 107.3 |
S1—C15—H15B | 108.2 | C34—C35—C33 | 108.0 (2) |
H15A—C15—H15B | 107.4 | C34—C35—C36 | 113.5 (2) |
C17—C16—S2 | 116.57 (18) | C33—C35—C36 | 109.8 (2) |
C17—C16—H16A | 108.2 | C34—C35—H35A | 108.5 |
S2—C16—H16A | 108.2 | C33—C35—H35A | 108.5 |
C17—C16—H16B | 108.2 | C36—C35—H35A | 108.5 |
S2—C16—H16B | 108.2 | N2—C36—C35 | 113.2 (2) |
H16A—C16—H16B | 107.3 | N2—C36—H36A | 108.9 |
C18—C17—C15 | 114.0 (2) | C35—C36—H36A | 108.9 |
C18—C17—C16 | 110.1 (2) | N2—C36—H36B | 108.9 |
C15—C17—C16 | 106.6 (2) | C35—C36—H36B | 108.9 |
C18—C17—H17A | 108.7 | H36A—C36—H36B | 107.8 |
| | | |
C6—C1—C2—C3 | −0.6 (4) | C24—C19—C20—C21 | 1.2 (4) |
C1—C2—C3—C4 | 0.9 (4) | C19—C20—C21—C22 | −0.8 (4) |
C2—C3—C4—C5 | 0.1 (4) | C20—C21—C22—C23 | 0.1 (4) |
C3—C4—C5—C6 | −1.2 (5) | C21—C22—C23—C24 | 0.2 (4) |
C2—C1—C6—C5 | −0.5 (4) | C22—C23—C24—C19 | 0.2 (4) |
C2—C1—C6—C7 | −179.3 (2) | C22—C23—C24—C25 | −179.4 (2) |
C4—C5—C6—C1 | 1.3 (4) | C20—C19—C24—C23 | −0.9 (4) |
C4—C5—C6—C7 | −179.9 (3) | C20—C19—C24—C25 | 178.7 (2) |
C1—C6—C7—S1 | −119.9 (2) | C23—C24—C25—S3 | −93.7 (3) |
C5—C6—C7—S1 | 61.3 (3) | C19—C24—C25—S3 | 86.8 (3) |
C15—S1—C7—C6 | 60.9 (2) | C33—S3—C25—C24 | 68.4 (2) |
C13—C8—C9—C10 | −0.6 (4) | C31—C26—C27—C28 | 1.1 (4) |
C8—C9—C10—C11 | 0.8 (4) | C26—C27—C28—C29 | −1.4 (4) |
C9—C10—C11—C12 | −0.5 (4) | C27—C28—C29—C30 | 0.5 (5) |
C10—C11—C12—C13 | −0.1 (4) | C28—C29—C30—C31 | 0.7 (5) |
C9—C8—C13—C12 | 0.0 (4) | C27—C26—C31—C30 | 0.1 (4) |
C9—C8—C13—C14 | 179.2 (2) | C27—C26—C31—C32 | 177.7 (2) |
C11—C12—C13—C8 | 0.4 (4) | C29—C30—C31—C26 | −1.0 (4) |
C11—C12—C13—C14 | −178.8 (2) | C29—C30—C31—C32 | −178.7 (3) |
C8—C13—C14—S2 | 94.9 (3) | C26—C31—C32—S4 | 126.3 (2) |
C12—C13—C14—S2 | −86.0 (3) | C30—C31—C32—S4 | −56.1 (3) |
C16—S2—C14—C13 | −66.4 (2) | C34—S4—C32—C31 | −59.1 (2) |
C7—S1—C15—C17 | 71.4 (2) | C25—S3—C33—C35 | 67.4 (2) |
C14—S2—C16—C17 | −66.1 (2) | C32—S4—C34—C35 | −70.6 (2) |
S1—C15—C17—C18 | 49.4 (3) | S4—C34—C35—C33 | −176.04 (18) |
S1—C15—C17—C16 | 171.03 (17) | S4—C34—C35—C36 | −54.1 (3) |
S2—C16—C17—C18 | −67.5 (3) | S3—C33—C35—C34 | −169.65 (17) |
S2—C16—C17—C15 | 168.42 (17) | S3—C33—C35—C36 | 66.1 (3) |
C15—C17—C18—N1 | −84.8 (3) | C34—C35—C36—N2 | 83.5 (3) |
C16—C17—C18—N1 | 155.4 (2) | C33—C35—C36—N2 | −155.5 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···Cl2i | 0.91 | 2.24 | 3.126 (2) | 163 |
N1—H1C···S1 | 0.91 | 2.59 | 3.216 (2) | 126 |
N1—H1C···Cl2ii | 0.91 | 2.66 | 3.242 (2) | 122 |
N1—H1D···Cl1 | 0.91 | 2.29 | 3.195 (3) | 174 |
N2—H2B···Cl1iii | 0.91 | 2.25 | 3.123 (2) | 161 |
N2—H2C···Cl2 | 0.91 | 2.30 | 3.207 (3) | 174 |
N2—H2D···S4 | 0.91 | 2.62 | 3.238 (2) | 126 |
N2—H2D···Cl1iv | 0.91 | 2.70 | 3.190 (2) | 114 |
Symmetry codes: (i) −x+1, −y+1, z−1; (ii) x+1, y, z−1; (iii) −x+1, −y+1, z; (iv) x−1, y, z. |