The title compound [systematic name: 1-methyl-4-{3-[2-(trifluoromethyl)-10
H-phenothiazin-10-yl]propyl}piperazine- 1,4-diium bis(2,4,6-trinitrophenolate)], C
21H
26F
3N
2S
+·2C
6H
2N
3O
7−, belongs to a group of phenothiazine derivatives which exhibit tranquillizing activity. The dihedral angle between the two outer aromatic rings of the phenothiazine unit is 24.69 (7)°. The crystal packing is stabilized by N—H
O hydrogen bonds and several weak C—H
O contacts. The molecular conformation of the trifluoperazinium cation differs significantly from that in the hydrochloride.
Supporting information
CCDC reference: 643087
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.004 Å
- R factor = 0.055
- wR factor = 0.149
- Data-to-parameter ratio = 12.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.99
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 700 Deg.
PLAT432_ALERT_2_C Short Inter X...Y Contact O461 .. C3 .. 3.01 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact C43 .. C53 .. 3.18 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 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
0 ALERT type 5 Informative message, check
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).
1-methyl-4-{3-[2-(trifluoromethyl)-10
H-phenothiazin-10-yl]propyl}piperazine- 1,4-diium bis(2,4,6-trinitrophenolate)
top
Crystal data top
C21H26F3N3S2+·2C6H2N3O7− | Z = 2 |
Mr = 865.72 | F(000) = 892 |
Triclinic, P1 | Dx = 1.556 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.1472 (7) Å | Cell parameters from 17175 reflections |
b = 12.5927 (12) Å | θ = 3.5–25.6° |
c = 19.6752 (18) Å | µ = 0.19 mm−1 |
α = 73.782 (7)° | T = 173 K |
β = 78.833 (7)° | Block, yellow |
γ = 73.959 (7)° | 0.23 × 0.20 × 0.19 mm |
V = 1847.9 (3) Å3 | |
Data collection top
Stoe IPDSII two-circle diffractometer | 6895 independent reflections |
Radiation source: fine-focus sealed tube | 5091 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.078 |
ω scans | θmax = 25.7°, θmin = 3.5° |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −9→9 |
Tmin = 0.969, Tmax = 0.976 | k = −15→15 |
19064 measured reflections | l = −23→23 |
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)] = 0.055 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.149 | w = 1/[σ2(Fo2) + (0.0901P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
6895 reflections | Δρmax = 0.34 e Å−3 |
550 parameters | Δρmin = −0.42 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0142 (18) |
Special details top
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 | |
S1 | 0.75390 (10) | 0.65335 (7) | 0.34254 (3) | 0.0483 (2) | |
N1 | 0.6763 (3) | 0.59932 (19) | 0.50475 (10) | 0.0377 (5) | |
C1 | 0.5799 (3) | 0.5811 (2) | 0.57640 (12) | 0.0385 (6) | |
H1A | 0.5146 | 0.5233 | 0.5812 | 0.046* | |
H1B | 0.4951 | 0.6530 | 0.5809 | 0.046* | |
C2 | 0.6884 (3) | 0.5424 (2) | 0.63893 (12) | 0.0353 (5) | |
H2A | 0.7880 | 0.4791 | 0.6311 | 0.042* | |
H2B | 0.7323 | 0.6062 | 0.6426 | 0.042* | |
C3 | 0.5726 (3) | 0.5034 (2) | 0.70728 (11) | 0.0300 (5) | |
H3A | 0.4588 | 0.5579 | 0.7073 | 0.036* | |
H3B | 0.5551 | 0.4280 | 0.7086 | 0.036* | |
C11 | 0.7634 (3) | 0.7392 (2) | 0.39868 (14) | 0.0427 (6) | |
C12 | 0.7173 (3) | 0.7059 (2) | 0.47322 (13) | 0.0376 (6) | |
C13 | 0.7086 (4) | 0.7836 (2) | 0.51336 (13) | 0.0405 (6) | |
H13 | 0.6775 | 0.7638 | 0.5636 | 0.049* | |
C14 | 0.7448 (4) | 0.8898 (2) | 0.48081 (15) | 0.0446 (6) | |
C15 | 0.7933 (4) | 0.9205 (3) | 0.40793 (16) | 0.0514 (7) | |
H15 | 0.8208 | 0.9920 | 0.3863 | 0.062* | |
C16 | 0.8012 (4) | 0.8452 (3) | 0.36705 (15) | 0.0499 (7) | |
H16 | 0.8327 | 0.8659 | 0.3169 | 0.060* | |
C17 | 0.7334 (4) | 0.9696 (3) | 0.52688 (17) | 0.0518 (7) | |
F1 | 0.8735 (3) | 0.94831 (18) | 0.55899 (13) | 0.0767 (6) | |
F2 | 0.7078 (3) | 1.07926 (15) | 0.49009 (11) | 0.0723 (6) | |
F3 | 0.6011 (3) | 0.96499 (16) | 0.58015 (10) | 0.0650 (5) | |
C21 | 0.8047 (3) | 0.5178 (2) | 0.40137 (13) | 0.0402 (6) | |
C22 | 0.7531 (3) | 0.5039 (2) | 0.47552 (14) | 0.0388 (6) | |
C23 | 0.7750 (4) | 0.3922 (2) | 0.51762 (15) | 0.0469 (7) | |
H23 | 0.7424 | 0.3796 | 0.5677 | 0.056* | |
C24 | 0.8441 (4) | 0.2991 (3) | 0.48698 (18) | 0.0556 (8) | |
H24 | 0.8561 | 0.2241 | 0.5164 | 0.067* | |
C25 | 0.8958 (4) | 0.3150 (3) | 0.41372 (18) | 0.0581 (8) | |
H25 | 0.9433 | 0.2514 | 0.3932 | 0.070* | |
C26 | 0.8769 (4) | 0.4243 (3) | 0.37164 (16) | 0.0480 (7) | |
H26 | 0.9134 | 0.4361 | 0.3218 | 0.058* | |
N31 | 0.6503 (2) | 0.49511 (16) | 0.77281 (9) | 0.0257 (4) | |
H31 | 0.675 (4) | 0.563 (3) | 0.7710 (17) | 0.060 (10)* | |
C32 | 0.5251 (3) | 0.47338 (19) | 0.83902 (11) | 0.0276 (5) | |
H32A | 0.4905 | 0.4021 | 0.8432 | 0.033* | |
H32B | 0.4205 | 0.5365 | 0.8355 | 0.033* | |
C33 | 0.6046 (3) | 0.46342 (19) | 0.90526 (12) | 0.0297 (5) | |
H33A | 0.6270 | 0.5376 | 0.9035 | 0.036* | |
H33B | 0.5221 | 0.4446 | 0.9483 | 0.036* | |
N34 | 0.7706 (2) | 0.37323 (16) | 0.91084 (9) | 0.0278 (4) | |
H34 | 0.738 (3) | 0.304 (2) | 0.9147 (12) | 0.025 (6)* | |
C35 | 0.8942 (3) | 0.39655 (19) | 0.84446 (12) | 0.0296 (5) | |
H35A | 1.0008 | 0.3350 | 0.8478 | 0.036* | |
H35B | 0.9253 | 0.4692 | 0.8397 | 0.036* | |
C36 | 0.8142 (3) | 0.40357 (19) | 0.77949 (12) | 0.0295 (5) | |
H36A | 0.8970 | 0.4197 | 0.7361 | 0.035* | |
H36B | 0.7895 | 0.3293 | 0.7831 | 0.035* | |
C37 | 0.8482 (4) | 0.3664 (2) | 0.97560 (13) | 0.0387 (6) | |
H37A | 0.7654 | 0.3510 | 1.0183 | 0.058* | |
H37B | 0.8769 | 0.4389 | 0.9713 | 0.058* | |
H37C | 0.9530 | 0.3050 | 0.9795 | 0.058* | |
O51 | 0.6255 (2) | 0.21501 (13) | 0.89629 (9) | 0.0350 (4) | |
C51 | 0.6304 (3) | 0.11100 (19) | 0.90624 (11) | 0.0262 (5) | |
C52 | 0.7795 (3) | 0.01779 (18) | 0.92191 (11) | 0.0267 (5) | |
C53 | 0.7779 (3) | −0.09542 (19) | 0.93266 (11) | 0.0277 (5) | |
H53 | 0.8785 | −0.1534 | 0.9438 | 0.033* | |
C54 | 0.6293 (3) | −0.12375 (18) | 0.92715 (11) | 0.0275 (5) | |
C55 | 0.4820 (3) | −0.03968 (19) | 0.90699 (11) | 0.0279 (5) | |
H55 | 0.3827 | −0.0593 | 0.9002 | 0.033* | |
C56 | 0.4860 (3) | 0.07239 (18) | 0.89732 (11) | 0.0269 (5) | |
N52 | 0.9443 (3) | 0.04101 (17) | 0.92217 (10) | 0.0315 (4) | |
O521 | 0.9480 (2) | 0.13312 (16) | 0.93278 (11) | 0.0439 (4) | |
O522 | 1.0755 (2) | −0.03240 (16) | 0.91221 (11) | 0.0467 (5) | |
N54 | 0.6271 (3) | −0.24302 (17) | 0.94000 (10) | 0.0332 (4) | |
O541 | 0.7607 (3) | −0.31667 (15) | 0.95400 (11) | 0.0456 (5) | |
O542 | 0.4929 (3) | −0.26624 (16) | 0.93510 (12) | 0.0490 (5) | |
N56 | 0.3355 (3) | 0.16030 (16) | 0.87195 (10) | 0.0320 (4) | |
O561 | 0.2769 (2) | 0.15165 (17) | 0.82133 (10) | 0.0457 (5) | |
O562 | 0.2763 (2) | 0.23848 (15) | 0.90304 (11) | 0.0452 (5) | |
O41 | 0.7878 (2) | 0.65962 (14) | 0.78078 (10) | 0.0385 (4) | |
C41 | 0.7875 (3) | 0.76401 (19) | 0.76718 (11) | 0.0290 (5) | |
C42 | 0.9314 (3) | 0.80130 (19) | 0.77838 (12) | 0.0282 (5) | |
C43 | 0.9330 (3) | 0.91392 (19) | 0.77010 (11) | 0.0298 (5) | |
H43 | 1.0290 | 0.9333 | 0.7801 | 0.036* | |
C44 | 0.7900 (3) | 0.99810 (19) | 0.74672 (12) | 0.0307 (5) | |
C45 | 0.6456 (3) | 0.9713 (2) | 0.73465 (12) | 0.0316 (5) | |
H45 | 0.5484 | 1.0297 | 0.7197 | 0.038* | |
C46 | 0.6455 (3) | 0.85808 (19) | 0.74477 (12) | 0.0298 (5) | |
N42 | 1.0804 (3) | 0.71506 (17) | 0.80547 (11) | 0.0333 (4) | |
O421 | 1.1473 (3) | 0.73111 (16) | 0.85151 (10) | 0.0463 (5) | |
O422 | 1.1337 (3) | 0.62991 (18) | 0.78118 (13) | 0.0608 (6) | |
N44 | 0.7883 (3) | 1.11711 (17) | 0.73900 (11) | 0.0370 (5) | |
O441 | 0.6707 (3) | 1.19139 (17) | 0.71103 (14) | 0.0648 (7) | |
O442 | 0.9034 (2) | 1.13822 (15) | 0.76209 (10) | 0.0413 (4) | |
N46 | 0.4865 (3) | 0.83597 (17) | 0.73433 (11) | 0.0369 (5) | |
O461 | 0.4940 (3) | 0.74691 (17) | 0.71697 (13) | 0.0568 (6) | |
O462 | 0.3513 (2) | 0.90678 (16) | 0.74188 (12) | 0.0509 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0508 (4) | 0.0594 (5) | 0.0307 (3) | −0.0100 (3) | −0.0023 (3) | −0.0091 (3) |
N1 | 0.0404 (12) | 0.0440 (12) | 0.0285 (10) | −0.0125 (10) | −0.0038 (8) | −0.0062 (9) |
C1 | 0.0378 (14) | 0.0491 (15) | 0.0292 (12) | −0.0154 (12) | −0.0057 (10) | −0.0044 (10) |
C2 | 0.0369 (13) | 0.0420 (14) | 0.0300 (11) | −0.0150 (11) | −0.0059 (10) | −0.0065 (10) |
C3 | 0.0339 (12) | 0.0307 (12) | 0.0288 (11) | −0.0124 (10) | −0.0071 (9) | −0.0055 (9) |
C11 | 0.0364 (14) | 0.0492 (16) | 0.0367 (13) | −0.0062 (12) | −0.0018 (10) | −0.0069 (11) |
C12 | 0.0332 (13) | 0.0404 (14) | 0.0343 (12) | −0.0086 (11) | −0.0043 (10) | −0.0013 (10) |
C13 | 0.0427 (15) | 0.0417 (14) | 0.0332 (12) | −0.0103 (12) | −0.0045 (10) | −0.0027 (10) |
C14 | 0.0422 (15) | 0.0399 (15) | 0.0458 (15) | −0.0076 (12) | −0.0046 (12) | −0.0034 (12) |
C15 | 0.0500 (17) | 0.0418 (16) | 0.0539 (17) | −0.0138 (13) | 0.0022 (13) | −0.0008 (13) |
C16 | 0.0489 (17) | 0.0482 (17) | 0.0401 (14) | −0.0103 (13) | 0.0037 (12) | 0.0019 (12) |
C17 | 0.0530 (18) | 0.0383 (16) | 0.0612 (18) | −0.0102 (13) | −0.0083 (14) | −0.0073 (13) |
F1 | 0.0667 (13) | 0.0687 (13) | 0.1066 (16) | −0.0046 (10) | −0.0335 (12) | −0.0359 (12) |
F2 | 0.1001 (16) | 0.0356 (10) | 0.0769 (13) | −0.0150 (10) | −0.0132 (11) | −0.0061 (9) |
F3 | 0.0749 (13) | 0.0562 (11) | 0.0623 (11) | −0.0112 (10) | 0.0014 (9) | −0.0226 (9) |
C21 | 0.0322 (13) | 0.0507 (16) | 0.0403 (13) | −0.0126 (12) | −0.0049 (10) | −0.0121 (12) |
C22 | 0.0366 (14) | 0.0435 (14) | 0.0420 (13) | −0.0134 (11) | −0.0125 (11) | −0.0104 (11) |
C23 | 0.0572 (18) | 0.0484 (16) | 0.0405 (14) | −0.0169 (14) | −0.0156 (12) | −0.0084 (12) |
C24 | 0.060 (2) | 0.0454 (17) | 0.0672 (19) | −0.0136 (14) | −0.0251 (16) | −0.0104 (14) |
C25 | 0.0523 (18) | 0.0577 (19) | 0.075 (2) | −0.0094 (15) | −0.0148 (16) | −0.0321 (17) |
C26 | 0.0366 (15) | 0.0595 (19) | 0.0523 (16) | −0.0109 (13) | −0.0061 (12) | −0.0203 (14) |
N31 | 0.0284 (10) | 0.0230 (10) | 0.0265 (9) | −0.0064 (8) | −0.0046 (7) | −0.0059 (7) |
C32 | 0.0275 (11) | 0.0249 (11) | 0.0283 (11) | −0.0042 (9) | −0.0026 (9) | −0.0052 (8) |
C33 | 0.0345 (12) | 0.0245 (11) | 0.0288 (11) | −0.0038 (9) | −0.0039 (9) | −0.0073 (9) |
N34 | 0.0315 (10) | 0.0238 (10) | 0.0299 (10) | −0.0077 (8) | −0.0087 (8) | −0.0049 (7) |
C35 | 0.0286 (12) | 0.0239 (11) | 0.0337 (12) | −0.0056 (9) | −0.0064 (9) | −0.0018 (9) |
C36 | 0.0293 (12) | 0.0252 (11) | 0.0314 (11) | −0.0036 (9) | −0.0024 (9) | −0.0066 (9) |
C37 | 0.0471 (15) | 0.0370 (14) | 0.0359 (13) | −0.0106 (11) | −0.0171 (11) | −0.0063 (10) |
O51 | 0.0369 (9) | 0.0210 (8) | 0.0503 (10) | −0.0082 (7) | −0.0123 (7) | −0.0077 (7) |
C51 | 0.0277 (11) | 0.0254 (11) | 0.0263 (10) | −0.0078 (9) | −0.0022 (8) | −0.0071 (8) |
C52 | 0.0267 (11) | 0.0245 (11) | 0.0291 (11) | −0.0073 (9) | −0.0049 (9) | −0.0047 (8) |
C53 | 0.0289 (12) | 0.0243 (11) | 0.0277 (11) | −0.0043 (9) | −0.0023 (9) | −0.0059 (8) |
C54 | 0.0323 (12) | 0.0203 (11) | 0.0302 (11) | −0.0082 (9) | −0.0007 (9) | −0.0067 (8) |
C55 | 0.0270 (11) | 0.0269 (11) | 0.0313 (11) | −0.0089 (9) | −0.0004 (9) | −0.0092 (9) |
C56 | 0.0255 (11) | 0.0221 (11) | 0.0310 (11) | −0.0037 (9) | −0.0027 (9) | −0.0055 (8) |
N52 | 0.0293 (11) | 0.0313 (11) | 0.0349 (10) | −0.0090 (9) | −0.0084 (8) | −0.0045 (8) |
O521 | 0.0404 (10) | 0.0391 (10) | 0.0621 (12) | −0.0142 (8) | −0.0123 (9) | −0.0189 (9) |
O522 | 0.0259 (9) | 0.0366 (10) | 0.0741 (13) | −0.0026 (8) | −0.0078 (8) | −0.0117 (9) |
N54 | 0.0381 (12) | 0.0239 (10) | 0.0381 (11) | −0.0090 (9) | −0.0015 (9) | −0.0087 (8) |
O541 | 0.0480 (11) | 0.0238 (9) | 0.0617 (12) | 0.0000 (8) | −0.0133 (9) | −0.0088 (8) |
O542 | 0.0437 (11) | 0.0314 (10) | 0.0770 (13) | −0.0168 (8) | −0.0067 (9) | −0.0139 (9) |
N56 | 0.0279 (10) | 0.0255 (10) | 0.0398 (11) | −0.0062 (8) | −0.0056 (8) | −0.0028 (8) |
O561 | 0.0449 (11) | 0.0477 (11) | 0.0435 (10) | −0.0067 (9) | −0.0183 (8) | −0.0048 (8) |
O562 | 0.0362 (10) | 0.0304 (10) | 0.0689 (12) | 0.0032 (8) | −0.0102 (9) | −0.0202 (9) |
O41 | 0.0428 (10) | 0.0231 (9) | 0.0531 (10) | −0.0088 (7) | −0.0174 (8) | −0.0061 (7) |
C41 | 0.0358 (13) | 0.0250 (11) | 0.0279 (11) | −0.0079 (9) | −0.0042 (9) | −0.0082 (8) |
C42 | 0.0293 (12) | 0.0241 (11) | 0.0313 (11) | −0.0037 (9) | −0.0036 (9) | −0.0093 (9) |
C43 | 0.0320 (12) | 0.0280 (12) | 0.0313 (11) | −0.0098 (10) | 0.0016 (9) | −0.0113 (9) |
C44 | 0.0347 (13) | 0.0233 (11) | 0.0343 (12) | −0.0076 (9) | −0.0012 (9) | −0.0086 (9) |
C45 | 0.0329 (12) | 0.0260 (11) | 0.0341 (12) | −0.0047 (9) | −0.0035 (9) | −0.0071 (9) |
C46 | 0.0296 (12) | 0.0275 (12) | 0.0329 (11) | −0.0083 (9) | −0.0036 (9) | −0.0070 (9) |
N42 | 0.0314 (11) | 0.0292 (11) | 0.0408 (11) | −0.0041 (8) | −0.0078 (8) | −0.0113 (8) |
O421 | 0.0507 (11) | 0.0465 (11) | 0.0442 (10) | −0.0010 (9) | −0.0202 (9) | −0.0158 (8) |
O422 | 0.0504 (13) | 0.0443 (12) | 0.0986 (17) | 0.0131 (9) | −0.0303 (12) | −0.0444 (12) |
N44 | 0.0430 (12) | 0.0233 (10) | 0.0441 (11) | −0.0083 (9) | −0.0004 (9) | −0.0102 (8) |
O441 | 0.0694 (15) | 0.0258 (10) | 0.1000 (17) | −0.0046 (10) | −0.0341 (13) | −0.0069 (10) |
O442 | 0.0466 (11) | 0.0314 (9) | 0.0514 (10) | −0.0170 (8) | 0.0002 (8) | −0.0154 (8) |
N46 | 0.0337 (11) | 0.0290 (11) | 0.0479 (12) | −0.0064 (9) | −0.0110 (9) | −0.0065 (9) |
O461 | 0.0497 (12) | 0.0386 (11) | 0.0955 (16) | −0.0075 (9) | −0.0305 (11) | −0.0261 (11) |
O462 | 0.0299 (10) | 0.0380 (10) | 0.0814 (14) | −0.0043 (8) | −0.0099 (9) | −0.0108 (10) |
Geometric parameters (Å, º) top
S1—C21 | 1.766 (3) | N34—C37 | 1.501 (3) |
S1—C11 | 1.772 (3) | N34—H34 | 0.96 (3) |
N1—C22 | 1.413 (3) | C35—C36 | 1.514 (3) |
N1—C12 | 1.414 (3) | C35—H35A | 0.9900 |
N1—C1 | 1.465 (3) | C35—H35B | 0.9900 |
C1—C2 | 1.543 (3) | C36—H36A | 0.9900 |
C1—H1A | 0.9900 | C36—H36B | 0.9900 |
C1—H1B | 0.9900 | C37—H37A | 0.9800 |
C2—C3 | 1.529 (3) | C37—H37B | 0.9800 |
C2—H2A | 0.9900 | C37—H37C | 0.9800 |
C2—H2B | 0.9900 | O51—C51 | 1.260 (3) |
C3—N31 | 1.509 (3) | C51—C56 | 1.448 (3) |
C3—H3A | 0.9900 | C51—C52 | 1.450 (3) |
C3—H3B | 0.9900 | C52—C53 | 1.385 (3) |
C11—C16 | 1.397 (4) | C52—N52 | 1.452 (3) |
C11—C12 | 1.414 (4) | C53—C54 | 1.384 (3) |
C12—C13 | 1.399 (4) | C53—H53 | 0.9500 |
C13—C14 | 1.398 (4) | C54—C55 | 1.402 (3) |
C13—H13 | 0.9500 | C54—N54 | 1.456 (3) |
C14—C15 | 1.385 (4) | C55—C56 | 1.379 (3) |
C14—C17 | 1.505 (4) | C55—H55 | 0.9500 |
C15—C16 | 1.386 (4) | C56—N56 | 1.468 (3) |
C15—H15 | 0.9500 | N52—O522 | 1.229 (3) |
C16—H16 | 0.9500 | N52—O521 | 1.244 (3) |
C17—F1 | 1.338 (4) | N54—O542 | 1.234 (3) |
C17—F2 | 1.347 (3) | N54—O541 | 1.239 (3) |
C17—F3 | 1.351 (4) | N56—O561 | 1.227 (3) |
C21—C26 | 1.394 (4) | N56—O562 | 1.239 (3) |
C21—C22 | 1.413 (4) | O41—C41 | 1.265 (3) |
C22—C23 | 1.401 (4) | C41—C46 | 1.443 (3) |
C23—C24 | 1.397 (4) | C41—C42 | 1.451 (3) |
C23—H23 | 0.9500 | C42—C43 | 1.385 (3) |
C24—C25 | 1.395 (5) | C42—N42 | 1.462 (3) |
C24—H24 | 0.9500 | C43—C44 | 1.395 (3) |
C25—C26 | 1.378 (5) | C43—H43 | 0.9500 |
C25—H25 | 0.9500 | C44—C45 | 1.388 (3) |
C26—H26 | 0.9500 | C44—N44 | 1.460 (3) |
N31—C32 | 1.501 (3) | C45—C46 | 1.383 (3) |
N31—C36 | 1.504 (3) | C45—H45 | 0.9500 |
N31—H31 | 0.92 (4) | C46—N46 | 1.461 (3) |
C32—C33 | 1.525 (3) | N42—O421 | 1.230 (3) |
C32—H32A | 0.9900 | N42—O422 | 1.231 (3) |
C32—H32B | 0.9900 | N44—O441 | 1.232 (3) |
C33—N34 | 1.506 (3) | N44—O442 | 1.235 (3) |
C33—H33A | 0.9900 | N46—O462 | 1.224 (3) |
C33—H33B | 0.9900 | N46—O461 | 1.243 (3) |
N34—C35 | 1.499 (3) | | |
| | | |
C21—S1—C11 | 99.55 (12) | C32—C33—H33B | 109.3 |
C22—N1—C12 | 121.5 (2) | H33A—C33—H33B | 107.9 |
C22—N1—C1 | 118.4 (2) | C35—N34—C37 | 110.85 (19) |
C12—N1—C1 | 118.9 (2) | C35—N34—C33 | 110.24 (16) |
N1—C1—C2 | 115.9 (2) | C37—N34—C33 | 110.78 (18) |
N1—C1—H1A | 108.3 | C35—N34—H34 | 109.3 (14) |
C2—C1—H1A | 108.3 | C37—N34—H34 | 110.7 (14) |
N1—C1—H1B | 108.3 | C33—N34—H34 | 104.7 (15) |
C2—C1—H1B | 108.3 | N34—C35—C36 | 110.36 (19) |
H1A—C1—H1B | 107.4 | N34—C35—H35A | 109.6 |
C3—C2—C1 | 107.8 (2) | C36—C35—H35A | 109.6 |
C3—C2—H2A | 110.1 | N34—C35—H35B | 109.6 |
C1—C2—H2A | 110.1 | C36—C35—H35B | 109.6 |
C3—C2—H2B | 110.1 | H35A—C35—H35B | 108.1 |
C1—C2—H2B | 110.1 | N31—C36—C35 | 111.44 (18) |
H2A—C2—H2B | 108.5 | N31—C36—H36A | 109.3 |
N31—C3—C2 | 111.41 (19) | C35—C36—H36A | 109.3 |
N31—C3—H3A | 109.3 | N31—C36—H36B | 109.3 |
C2—C3—H3A | 109.3 | C35—C36—H36B | 109.3 |
N31—C3—H3B | 109.3 | H36A—C36—H36B | 108.0 |
C2—C3—H3B | 109.3 | N34—C37—H37A | 109.5 |
H3A—C3—H3B | 108.0 | N34—C37—H37B | 109.5 |
C16—C11—C12 | 120.8 (3) | H37A—C37—H37B | 109.5 |
C16—C11—S1 | 118.5 (2) | N34—C37—H37C | 109.5 |
C12—C11—S1 | 120.5 (2) | H37A—C37—H37C | 109.5 |
C13—C12—C11 | 117.4 (2) | H37B—C37—H37C | 109.5 |
C13—C12—N1 | 122.0 (2) | O51—C51—C56 | 122.1 (2) |
C11—C12—N1 | 120.5 (2) | O51—C51—C52 | 125.7 (2) |
C14—C13—C12 | 121.1 (2) | C56—C51—C52 | 112.10 (19) |
C14—C13—H13 | 119.4 | C53—C52—C51 | 123.4 (2) |
C12—C13—H13 | 119.4 | C53—C52—N52 | 116.35 (19) |
C15—C14—C13 | 120.9 (3) | C51—C52—N52 | 120.11 (19) |
C15—C14—C17 | 120.5 (3) | C54—C53—C52 | 119.8 (2) |
C13—C14—C17 | 118.6 (2) | C54—C53—H53 | 120.1 |
C14—C15—C16 | 119.0 (3) | C52—C53—H53 | 120.1 |
C14—C15—H15 | 120.5 | C53—C54—C55 | 121.3 (2) |
C16—C15—H15 | 120.5 | C53—C54—N54 | 119.6 (2) |
C15—C16—C11 | 120.8 (3) | C55—C54—N54 | 119.1 (2) |
C15—C16—H16 | 119.6 | C56—C55—C54 | 117.8 (2) |
C11—C16—H16 | 119.6 | C56—C55—H55 | 121.1 |
F1—C17—F2 | 106.2 (3) | C54—C55—H55 | 121.1 |
F1—C17—F3 | 105.4 (3) | C55—C56—C51 | 125.4 (2) |
F2—C17—F3 | 105.9 (2) | C55—C56—N56 | 117.5 (2) |
F1—C17—C14 | 114.0 (3) | C51—C56—N56 | 117.03 (19) |
F2—C17—C14 | 112.6 (3) | O522—N52—O521 | 122.5 (2) |
F3—C17—C14 | 112.1 (3) | O522—N52—C52 | 118.11 (19) |
C26—C21—C22 | 121.3 (3) | O521—N52—C52 | 119.4 (2) |
C26—C21—S1 | 117.8 (2) | O542—N54—O541 | 122.8 (2) |
C22—C21—S1 | 120.4 (2) | O542—N54—C54 | 118.4 (2) |
C23—C22—C21 | 117.1 (3) | O541—N54—C54 | 118.7 (2) |
C23—C22—N1 | 122.1 (2) | O561—N56—O562 | 124.3 (2) |
C21—C22—N1 | 120.7 (2) | O561—N56—C56 | 117.88 (19) |
C24—C23—C22 | 121.0 (3) | O562—N56—C56 | 117.78 (19) |
C24—C23—H23 | 119.5 | O41—C41—C46 | 125.8 (2) |
C22—C23—H23 | 119.5 | O41—C41—C42 | 121.7 (2) |
C25—C24—C23 | 120.9 (3) | C46—C41—C42 | 112.4 (2) |
C25—C24—H24 | 119.6 | C43—C42—C41 | 124.4 (2) |
C23—C24—H24 | 119.6 | C43—C42—N42 | 116.9 (2) |
C26—C25—C24 | 118.9 (3) | C41—C42—N42 | 118.52 (19) |
C26—C25—H25 | 120.5 | C42—C43—C44 | 118.3 (2) |
C24—C25—H25 | 120.5 | C42—C43—H43 | 120.9 |
C25—C26—C21 | 120.8 (3) | C44—C43—H43 | 120.9 |
C25—C26—H26 | 119.6 | C45—C44—C43 | 121.7 (2) |
C21—C26—H26 | 119.6 | C45—C44—N44 | 119.2 (2) |
C32—N31—C36 | 109.94 (16) | C43—C44—N44 | 119.0 (2) |
C32—N31—C3 | 111.03 (17) | C46—C45—C44 | 118.9 (2) |
C36—N31—C3 | 111.31 (17) | C46—C45—H45 | 120.5 |
C32—N31—H31 | 106 (2) | C44—C45—H45 | 120.5 |
C36—N31—H31 | 108 (2) | C45—C46—C41 | 124.2 (2) |
C3—N31—H31 | 111 (2) | C45—C46—N46 | 115.9 (2) |
N31—C32—C33 | 110.96 (18) | C41—C46—N46 | 119.8 (2) |
N31—C32—H32A | 109.4 | O421—N42—O422 | 122.9 (2) |
C33—C32—H32A | 109.4 | O421—N42—C42 | 118.36 (19) |
N31—C32—H32B | 109.4 | O422—N42—C42 | 118.71 (19) |
C33—C32—H32B | 109.4 | O441—N44—O442 | 123.2 (2) |
H32A—C32—H32B | 108.0 | O441—N44—C44 | 118.5 (2) |
N34—C33—C32 | 111.70 (18) | O442—N44—C44 | 118.3 (2) |
N34—C33—H33A | 109.3 | O462—N46—O461 | 122.5 (2) |
C32—C33—H33A | 109.3 | O462—N46—C46 | 118.7 (2) |
N34—C33—H33B | 109.3 | O461—N46—C46 | 118.8 (2) |
| | | |
C22—N1—C1—C2 | 82.6 (3) | N34—C35—C36—N31 | 58.5 (2) |
C12—N1—C1—C2 | −85.3 (3) | O51—C51—C52—C53 | 179.8 (2) |
N1—C1—C2—C3 | −167.8 (2) | C56—C51—C52—C53 | −4.9 (3) |
C1—C2—C3—N31 | −164.1 (2) | O51—C51—C52—N52 | −4.5 (3) |
C21—S1—C11—C16 | 153.9 (2) | C56—C51—C52—N52 | 170.86 (19) |
C21—S1—C11—C12 | −32.1 (2) | C51—C52—C53—C54 | 1.3 (3) |
C16—C11—C12—C13 | 1.0 (4) | N52—C52—C53—C54 | −174.55 (19) |
S1—C11—C12—C13 | −172.8 (2) | C52—C53—C54—C55 | 3.5 (3) |
C16—C11—C12—N1 | 178.9 (2) | C52—C53—C54—N54 | −178.69 (19) |
S1—C11—C12—N1 | 5.1 (3) | C53—C54—C55—C56 | −4.2 (3) |
C22—N1—C12—C13 | −151.2 (2) | N54—C54—C55—C56 | 178.1 (2) |
C1—N1—C12—C13 | 16.4 (4) | C54—C55—C56—C51 | 0.0 (3) |
C22—N1—C12—C11 | 31.1 (3) | C54—C55—C56—N56 | 176.32 (19) |
C1—N1—C12—C11 | −161.4 (2) | O51—C51—C56—C55 | 179.8 (2) |
C11—C12—C13—C14 | −0.2 (4) | C52—C51—C56—C55 | 4.2 (3) |
N1—C12—C13—C14 | −178.1 (2) | O51—C51—C56—N56 | 3.5 (3) |
C12—C13—C14—C15 | −1.1 (4) | C52—C51—C56—N56 | −172.10 (18) |
C12—C13—C14—C17 | −179.9 (3) | C53—C52—N52—O522 | 19.5 (3) |
C13—C14—C15—C16 | 1.7 (4) | C51—C52—N52—O522 | −156.5 (2) |
C17—C14—C15—C16 | −179.5 (3) | C53—C52—N52—O521 | −160.1 (2) |
C14—C15—C16—C11 | −0.9 (4) | C51—C52—N52—O521 | 23.9 (3) |
C12—C11—C16—C15 | −0.5 (4) | C53—C54—N54—O542 | 179.7 (2) |
S1—C11—C16—C15 | 173.5 (2) | C55—C54—N54—O542 | −2.5 (3) |
C15—C14—C17—F1 | −96.9 (3) | C53—C54—N54—O541 | −1.7 (3) |
C13—C14—C17—F1 | 81.9 (4) | C55—C54—N54—O541 | 176.1 (2) |
C15—C14—C17—F2 | 24.1 (4) | C55—C56—N56—O561 | −46.8 (3) |
C13—C14—C17—F2 | −157.1 (3) | C51—C56—N56—O561 | 129.8 (2) |
C15—C14—C17—F3 | 143.5 (3) | C55—C56—N56—O562 | 133.3 (2) |
C13—C14—C17—F3 | −37.8 (4) | C51—C56—N56—O562 | −50.1 (3) |
C11—S1—C21—C26 | −155.1 (2) | O41—C41—C42—C43 | −174.5 (2) |
C11—S1—C21—C22 | 32.9 (2) | C46—C41—C42—C43 | 1.2 (3) |
C26—C21—C22—C23 | −1.0 (4) | O41—C41—C42—N42 | 0.6 (3) |
S1—C21—C22—C23 | 170.8 (2) | C46—C41—C42—N42 | 176.27 (19) |
C26—C21—C22—N1 | −178.5 (2) | C41—C42—C43—C44 | −2.7 (3) |
S1—C21—C22—N1 | −6.7 (3) | N42—C42—C43—C44 | −177.81 (19) |
C12—N1—C22—C23 | 152.4 (2) | C42—C43—C44—C45 | 2.7 (3) |
C1—N1—C22—C23 | −15.2 (3) | C42—C43—C44—N44 | 178.9 (2) |
C12—N1—C22—C21 | −30.2 (3) | C43—C44—C45—C46 | −1.3 (3) |
C1—N1—C22—C21 | 162.1 (2) | N44—C44—C45—C46 | −177.5 (2) |
C21—C22—C23—C24 | −0.4 (4) | C44—C45—C46—C41 | −0.2 (4) |
N1—C22—C23—C24 | 177.1 (3) | C44—C45—C46—N46 | 177.2 (2) |
C22—C23—C24—C25 | 1.1 (5) | O41—C41—C46—C45 | 175.8 (2) |
C23—C24—C25—C26 | −0.3 (5) | C42—C41—C46—C45 | 0.3 (3) |
C24—C25—C26—C21 | −1.1 (4) | O41—C41—C46—N46 | −1.6 (4) |
C22—C21—C26—C25 | 1.7 (4) | C42—C41—C46—N46 | −177.1 (2) |
S1—C21—C26—C25 | −170.2 (2) | C43—C42—N42—O421 | 37.5 (3) |
C2—C3—N31—C32 | 171.74 (19) | C41—C42—N42—O421 | −138.0 (2) |
C2—C3—N31—C36 | −65.4 (2) | C43—C42—N42—O422 | −142.4 (2) |
C36—N31—C32—C33 | 55.6 (2) | C41—C42—N42—O422 | 42.2 (3) |
C3—N31—C32—C33 | 179.20 (17) | C45—C44—N44—O441 | −11.5 (4) |
N31—C32—C33—N34 | −55.6 (2) | C43—C44—N44—O441 | 172.2 (2) |
C32—C33—N34—C35 | 55.9 (2) | C45—C44—N44—O442 | 167.1 (2) |
C32—C33—N34—C37 | 178.92 (19) | C43—C44—N44—O442 | −9.1 (3) |
C37—N34—C35—C36 | −179.82 (18) | C45—C46—N46—O462 | −24.6 (3) |
C33—N34—C35—C36 | −56.8 (2) | C41—C46—N46—O462 | 152.9 (2) |
C32—N31—C36—C35 | −57.6 (2) | C45—C46—N46—O461 | 154.2 (2) |
C3—N31—C36—C35 | 178.95 (18) | C41—C46—N46—O461 | −28.2 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N31—H31···O41 | 0.92 (4) | 1.79 (4) | 2.666 (3) | 160 (3) |
N31—H31···O461 | 0.92 (4) | 2.46 (3) | 3.041 (3) | 122 (3) |
N34—H34···O51 | 0.96 (3) | 1.77 (3) | 2.683 (2) | 157 (2) |
N34—H34···O521 | 0.96 (3) | 2.33 (3) | 2.918 (3) | 118.8 (18) |
C16—H16···O442i | 0.95 | 2.39 | 3.147 (3) | 136 |
C32—H32A···O51 | 0.99 | 2.34 | 3.060 (3) | 129 |
C35—H35B···O41 | 0.99 | 2.41 | 3.132 (3) | 129 |
C36—H36B···O442ii | 0.99 | 2.45 | 3.318 (3) | 146 |
C55—H55···O522iii | 0.95 | 2.40 | 3.269 (3) | 151 |
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) x, y−1, z; (iii) x−1, y, z. |