The title compound [systematic name: 1-methyl-3-(10
H-phenothiazin-10-ylmethyl)piperidinium 2,4,6-trinitrophenolate], C
19H
23N
2S
+.C
6H
2N
3O
7−, is a pharmacologically active compound. The dihedral angle between the two outer aromatic rings of the phenothiazine unit is 41.58 (7)°. The crystal packing is stabilized by N—H
O hydrogen bonds and several weak C—H
O contacts.
Supporting information
CCDC reference: 643086
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.002 Å
- R factor = 0.036
- wR factor = 0.097
- Data-to-parameter ratio = 13.4
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact O361 .. N34 .. 2.86 Ang.
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
0 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 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-3-(10
H-phenothiazin-10-ylmethyl)piperidinium
2,4,6-trinitrophenolate
top
Crystal data top
C19H23N2S+·C6H2N3O7− | Z = 2 |
Mr = 539.56 | F(000) = 564 |
Triclinic, P1 | Dx = 1.431 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.3584 (9) Å | Cell parameters from 11665 reflections |
b = 10.7782 (9) Å | θ = 3.6–25.7° |
c = 14.5062 (13) Å | µ = 0.19 mm−1 |
α = 93.524 (7)° | T = 173 K |
β = 99.629 (8)° | Block, yellow |
γ = 102.419 (7)° | 0.45 × 0.45 × 0.40 mm |
V = 1251.8 (2) Å3 | |
Data collection top
Stoe IPDSII two-circle diffractometer | 4656 independent reflections |
Radiation source: fine-focus sealed tube | 3824 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
ω scans | θmax = 25.6°, θmin = 3.5° |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −10→9 |
Tmin = 0.911, Tmax = 0.920 | k = −13→13 |
12751 measured reflections | l = −17→17 |
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)] = 0.037 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.098 | w = 1/[σ2(Fo2) + (0.0554P)2 + 0.2289P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
4656 reflections | Δρmax = 0.24 e Å−3 |
348 parameters | Δρmin = −0.31 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: 0.0154 (19) |
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 | 0.02175 (7) | 0.37989 (5) | 0.35523 (3) | 0.04206 (15) | |
N1 | 0.28825 (18) | 0.24026 (12) | 0.40629 (9) | 0.0268 (3) | |
C1 | 0.3945 (2) | 0.14854 (15) | 0.40418 (11) | 0.0281 (4) | |
H1A | 0.3353 | 0.0661 | 0.4218 | 0.034* | |
H1B | 0.4974 | 0.1801 | 0.4519 | 0.034* | |
C2 | 0.4430 (2) | 0.12556 (14) | 0.30814 (11) | 0.0237 (3) | |
H2 | 0.5123 | 0.2071 | 0.2933 | 0.028* | |
C3 | 0.28805 (19) | 0.08374 (14) | 0.23111 (11) | 0.0224 (3) | |
H3A | 0.2160 | 0.0047 | 0.2460 | 0.027* | |
H3B | 0.2238 | 0.1510 | 0.2280 | 0.027* | |
N4 | 0.33760 (16) | 0.05998 (12) | 0.13795 (9) | 0.0217 (3) | |
H4 | 0.402 (3) | 0.132 (2) | 0.1256 (14) | 0.041 (6)* | |
C5 | 0.4332 (2) | −0.04426 (14) | 0.13991 (12) | 0.0298 (4) | |
H5A | 0.4653 | −0.0579 | 0.0781 | 0.036* | |
H5B | 0.3614 | −0.1251 | 0.1522 | 0.036* | |
C6 | 0.5888 (2) | −0.00758 (16) | 0.21622 (13) | 0.0329 (4) | |
H6A | 0.6661 | 0.0675 | 0.1997 | 0.039* | |
H6B | 0.6460 | −0.0791 | 0.2195 | 0.039* | |
C7 | 0.5469 (2) | 0.02409 (15) | 0.31244 (13) | 0.0312 (4) | |
H7A | 0.6514 | 0.0558 | 0.3589 | 0.037* | |
H7B | 0.4838 | −0.0544 | 0.3335 | 0.037* | |
C8 | 0.1906 (2) | 0.03098 (15) | 0.06006 (12) | 0.0298 (4) | |
H8A | 0.1321 | 0.1006 | 0.0605 | 0.045* | |
H8B | 0.1149 | −0.0489 | 0.0685 | 0.045* | |
H8C | 0.2277 | 0.0221 | −0.0001 | 0.045* | |
C11 | 0.2373 (3) | 0.44361 (16) | 0.35978 (11) | 0.0330 (4) | |
C12 | 0.3513 (2) | 0.36750 (14) | 0.38561 (11) | 0.0275 (4) | |
C13 | 0.5205 (2) | 0.41886 (15) | 0.38934 (11) | 0.0322 (4) | |
H13 | 0.5990 | 0.3696 | 0.4094 | 0.039* | |
C14 | 0.5765 (3) | 0.54132 (16) | 0.36413 (12) | 0.0400 (5) | |
H14 | 0.6920 | 0.5744 | 0.3660 | 0.048* | |
C15 | 0.4627 (3) | 0.61440 (17) | 0.33643 (13) | 0.0466 (5) | |
H15 | 0.5000 | 0.6973 | 0.3182 | 0.056* | |
C16 | 0.2945 (3) | 0.56665 (17) | 0.33535 (12) | 0.0435 (5) | |
H16 | 0.2174 | 0.6180 | 0.3178 | 0.052* | |
C21 | 0.0389 (2) | 0.28760 (16) | 0.45189 (11) | 0.0318 (4) | |
C22 | 0.1689 (2) | 0.22330 (15) | 0.46664 (11) | 0.0267 (4) | |
C23 | 0.1764 (2) | 0.14648 (15) | 0.54057 (12) | 0.0316 (4) | |
H23 | 0.2651 | 0.1040 | 0.5525 | 0.038* | |
C24 | 0.0554 (3) | 0.13102 (17) | 0.59742 (13) | 0.0381 (4) | |
H24 | 0.0604 | 0.0762 | 0.6461 | 0.046* | |
C25 | −0.0716 (3) | 0.19527 (18) | 0.58296 (13) | 0.0411 (4) | |
H25 | −0.1538 | 0.1848 | 0.6216 | 0.049* | |
C26 | −0.0782 (2) | 0.27549 (18) | 0.51133 (13) | 0.0405 (4) | |
H26 | −0.1629 | 0.3223 | 0.5028 | 0.049* | |
O31 | 0.56325 (14) | 0.23524 (10) | 0.07476 (8) | 0.0273 (3) | |
C31 | 0.64495 (19) | 0.34878 (13) | 0.09897 (10) | 0.0198 (3) | |
C32 | 0.57653 (18) | 0.45812 (14) | 0.11859 (10) | 0.0205 (3) | |
C33 | 0.67187 (19) | 0.58233 (13) | 0.13681 (10) | 0.0207 (3) | |
H33 | 0.6202 | 0.6514 | 0.1459 | 0.025* | |
C34 | 0.84247 (19) | 0.60521 (13) | 0.14171 (10) | 0.0198 (3) | |
C35 | 0.92134 (19) | 0.50618 (13) | 0.12421 (10) | 0.0195 (3) | |
H35 | 1.0382 | 0.5225 | 0.1260 | 0.023* | |
C36 | 0.82353 (18) | 0.38509 (13) | 0.10438 (10) | 0.0189 (3) | |
N32 | 0.39911 (16) | 0.44032 (12) | 0.12034 (9) | 0.0230 (3) | |
N34 | 0.94252 (17) | 0.73405 (11) | 0.16701 (9) | 0.0236 (3) | |
N36 | 0.90516 (16) | 0.28134 (11) | 0.08304 (9) | 0.0216 (3) | |
O321 | 0.32327 (15) | 0.33772 (11) | 0.14170 (10) | 0.0359 (3) | |
O322 | 0.33216 (14) | 0.52989 (11) | 0.10250 (9) | 0.0322 (3) | |
O341 | 0.87183 (15) | 0.82411 (10) | 0.16471 (9) | 0.0347 (3) | |
O342 | 1.09587 (14) | 0.74930 (10) | 0.19020 (8) | 0.0293 (3) | |
O361 | 0.97890 (16) | 0.28866 (11) | 0.01673 (9) | 0.0351 (3) | |
O362 | 0.89583 (17) | 0.19274 (11) | 0.13283 (9) | 0.0367 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0489 (3) | 0.0552 (3) | 0.0284 (2) | 0.0316 (2) | −0.0013 (2) | 0.0060 (2) |
N1 | 0.0356 (8) | 0.0224 (6) | 0.0253 (7) | 0.0137 (6) | 0.0047 (6) | 0.0024 (5) |
C1 | 0.0349 (9) | 0.0234 (8) | 0.0280 (8) | 0.0124 (7) | 0.0032 (7) | 0.0040 (6) |
C2 | 0.0237 (8) | 0.0185 (7) | 0.0300 (8) | 0.0074 (6) | 0.0040 (7) | 0.0034 (6) |
C3 | 0.0215 (8) | 0.0192 (7) | 0.0285 (8) | 0.0060 (6) | 0.0090 (6) | 0.0017 (6) |
N4 | 0.0192 (7) | 0.0162 (6) | 0.0296 (7) | 0.0019 (5) | 0.0083 (5) | −0.0014 (5) |
C5 | 0.0322 (9) | 0.0202 (7) | 0.0421 (10) | 0.0088 (7) | 0.0184 (8) | 0.0007 (7) |
C6 | 0.0262 (9) | 0.0267 (8) | 0.0534 (11) | 0.0142 (7) | 0.0160 (8) | 0.0097 (8) |
C7 | 0.0268 (9) | 0.0263 (8) | 0.0435 (10) | 0.0127 (7) | 0.0052 (8) | 0.0079 (7) |
C8 | 0.0263 (9) | 0.0275 (8) | 0.0307 (9) | −0.0002 (7) | 0.0029 (7) | −0.0053 (7) |
C11 | 0.0543 (12) | 0.0319 (9) | 0.0178 (8) | 0.0229 (8) | 0.0041 (8) | 0.0015 (6) |
C12 | 0.0432 (10) | 0.0231 (8) | 0.0171 (7) | 0.0134 (7) | 0.0015 (7) | 0.0000 (6) |
C13 | 0.0466 (11) | 0.0244 (8) | 0.0233 (8) | 0.0090 (7) | 0.0000 (8) | −0.0016 (6) |
C14 | 0.0625 (13) | 0.0267 (9) | 0.0270 (9) | 0.0035 (8) | 0.0093 (9) | −0.0040 (7) |
C15 | 0.0900 (18) | 0.0238 (9) | 0.0296 (10) | 0.0142 (10) | 0.0190 (10) | 0.0043 (7) |
C16 | 0.0830 (17) | 0.0321 (9) | 0.0252 (9) | 0.0328 (10) | 0.0113 (10) | 0.0057 (7) |
C21 | 0.0363 (10) | 0.0343 (9) | 0.0235 (8) | 0.0126 (7) | −0.0012 (7) | −0.0049 (7) |
C22 | 0.0329 (9) | 0.0248 (7) | 0.0204 (7) | 0.0072 (7) | 0.0009 (7) | −0.0050 (6) |
C23 | 0.0390 (10) | 0.0273 (8) | 0.0286 (9) | 0.0099 (7) | 0.0040 (8) | 0.0007 (7) |
C24 | 0.0522 (12) | 0.0309 (9) | 0.0291 (9) | 0.0039 (8) | 0.0099 (8) | −0.0006 (7) |
C25 | 0.0457 (12) | 0.0407 (10) | 0.0367 (10) | 0.0067 (9) | 0.0148 (9) | −0.0048 (8) |
C26 | 0.0374 (11) | 0.0459 (10) | 0.0388 (10) | 0.0156 (9) | 0.0055 (8) | −0.0085 (8) |
O31 | 0.0253 (6) | 0.0207 (5) | 0.0337 (6) | −0.0022 (4) | 0.0111 (5) | −0.0035 (4) |
C31 | 0.0213 (8) | 0.0207 (7) | 0.0176 (7) | 0.0021 (6) | 0.0073 (6) | 0.0017 (5) |
C32 | 0.0159 (8) | 0.0248 (7) | 0.0217 (7) | 0.0039 (6) | 0.0067 (6) | 0.0027 (6) |
C33 | 0.0220 (8) | 0.0212 (7) | 0.0217 (7) | 0.0070 (6) | 0.0089 (6) | 0.0025 (6) |
C34 | 0.0212 (8) | 0.0171 (7) | 0.0209 (7) | 0.0015 (6) | 0.0075 (6) | 0.0011 (5) |
C35 | 0.0180 (8) | 0.0213 (7) | 0.0200 (7) | 0.0037 (6) | 0.0066 (6) | 0.0023 (6) |
C36 | 0.0207 (8) | 0.0190 (7) | 0.0187 (7) | 0.0058 (6) | 0.0072 (6) | 0.0009 (5) |
N32 | 0.0182 (7) | 0.0269 (7) | 0.0246 (7) | 0.0048 (5) | 0.0066 (5) | 0.0020 (5) |
N34 | 0.0259 (8) | 0.0195 (6) | 0.0257 (7) | 0.0024 (5) | 0.0101 (6) | 0.0007 (5) |
N36 | 0.0208 (7) | 0.0184 (6) | 0.0256 (7) | 0.0030 (5) | 0.0076 (5) | −0.0011 (5) |
O321 | 0.0234 (6) | 0.0305 (6) | 0.0553 (8) | 0.0005 (5) | 0.0164 (6) | 0.0100 (5) |
O322 | 0.0243 (6) | 0.0372 (6) | 0.0402 (7) | 0.0141 (5) | 0.0095 (5) | 0.0090 (5) |
O341 | 0.0363 (7) | 0.0184 (5) | 0.0532 (8) | 0.0085 (5) | 0.0173 (6) | −0.0002 (5) |
O342 | 0.0230 (6) | 0.0247 (6) | 0.0357 (7) | −0.0027 (5) | 0.0039 (5) | 0.0008 (5) |
O361 | 0.0434 (8) | 0.0352 (6) | 0.0359 (7) | 0.0151 (6) | 0.0255 (6) | 0.0031 (5) |
O362 | 0.0478 (8) | 0.0265 (6) | 0.0459 (7) | 0.0172 (5) | 0.0225 (6) | 0.0130 (5) |
Geometric parameters (Å, º) top
S1—C11 | 1.773 (2) | C14—C15 | 1.385 (3) |
S1—C21 | 1.7724 (18) | C14—H14 | 0.9500 |
N1—C22 | 1.424 (2) | C15—C16 | 1.386 (3) |
N1—C12 | 1.429 (2) | C15—H15 | 0.9500 |
N1—C1 | 1.466 (2) | C16—H16 | 0.9500 |
C1—C2 | 1.535 (2) | C21—C26 | 1.400 (3) |
C1—H1A | 0.9900 | C21—C22 | 1.404 (2) |
C1—H1B | 0.9900 | C22—C23 | 1.396 (2) |
C2—C3 | 1.527 (2) | C23—C24 | 1.398 (3) |
C2—C7 | 1.534 (2) | C23—H23 | 0.9500 |
C2—H2 | 1.0000 | C24—C25 | 1.381 (3) |
C3—N4 | 1.5012 (19) | C24—H24 | 0.9500 |
C3—H3A | 0.9900 | C25—C26 | 1.394 (3) |
C3—H3B | 0.9900 | C25—H25 | 0.9500 |
N4—C8 | 1.487 (2) | C26—H26 | 0.9500 |
N4—C5 | 1.5112 (19) | O31—C31 | 1.2628 (17) |
N4—H4 | 0.89 (2) | C31—C36 | 1.447 (2) |
C5—C6 | 1.522 (3) | C31—C32 | 1.449 (2) |
C5—H5A | 0.9900 | C32—C33 | 1.387 (2) |
C5—H5B | 0.9900 | C32—N32 | 1.4586 (19) |
C6—C7 | 1.531 (2) | C33—C34 | 1.383 (2) |
C6—H6A | 0.9900 | C33—H33 | 0.9500 |
C6—H6B | 0.9900 | C34—C35 | 1.401 (2) |
C7—H7A | 0.9900 | C34—N34 | 1.4484 (18) |
C7—H7B | 0.9900 | C35—C36 | 1.368 (2) |
C8—H8A | 0.9800 | C35—H35 | 0.9500 |
C8—H8B | 0.9800 | C36—N36 | 1.4724 (18) |
C8—H8C | 0.9800 | N32—O322 | 1.2356 (17) |
C11—C16 | 1.398 (3) | N32—O321 | 1.2358 (17) |
C11—C12 | 1.406 (2) | N34—O341 | 1.2395 (17) |
C12—C13 | 1.394 (3) | N34—O342 | 1.2416 (18) |
C13—C14 | 1.395 (2) | N36—O361 | 1.2240 (17) |
C13—H13 | 0.9500 | N36—O362 | 1.2294 (17) |
| | | |
C11—S1—C21 | 98.18 (8) | C12—C13—C14 | 121.14 (17) |
C22—N1—C12 | 117.14 (12) | C12—C13—H13 | 119.4 |
C22—N1—C1 | 118.35 (13) | C14—C13—H13 | 119.4 |
C12—N1—C1 | 118.43 (14) | C15—C14—C13 | 119.6 (2) |
N1—C1—C2 | 113.71 (12) | C15—C14—H14 | 120.2 |
N1—C1—H1A | 108.8 | C13—C14—H14 | 120.2 |
C2—C1—H1A | 108.8 | C14—C15—C16 | 120.05 (17) |
N1—C1—H1B | 108.8 | C14—C15—H15 | 120.0 |
C2—C1—H1B | 108.8 | C16—C15—H15 | 120.0 |
H1A—C1—H1B | 107.7 | C15—C16—C11 | 120.64 (18) |
C3—C2—C7 | 110.48 (13) | C15—C16—H16 | 119.7 |
C3—C2—C1 | 110.79 (13) | C11—C16—H16 | 119.7 |
C7—C2—C1 | 109.42 (13) | C26—C21—C22 | 120.16 (16) |
C3—C2—H2 | 108.7 | C26—C21—S1 | 120.68 (14) |
C7—C2—H2 | 108.7 | C22—C21—S1 | 119.13 (13) |
C1—C2—H2 | 108.7 | C23—C22—C21 | 118.42 (16) |
N4—C3—C2 | 110.09 (12) | C23—C22—N1 | 122.90 (15) |
N4—C3—H3A | 109.6 | C21—C22—N1 | 118.68 (14) |
C2—C3—H3A | 109.6 | C22—C23—C24 | 121.09 (17) |
N4—C3—H3B | 109.6 | C22—C23—H23 | 119.5 |
C2—C3—H3B | 109.6 | C24—C23—H23 | 119.5 |
H3A—C3—H3B | 108.2 | C25—C24—C23 | 120.18 (17) |
C8—N4—C3 | 111.41 (12) | C25—C24—H24 | 119.9 |
C8—N4—C5 | 111.58 (12) | C23—C24—H24 | 119.9 |
C3—N4—C5 | 110.92 (12) | C24—C25—C26 | 119.58 (18) |
C8—N4—H4 | 105.0 (14) | C24—C25—H25 | 120.2 |
C3—N4—H4 | 108.5 (13) | C26—C25—H25 | 120.2 |
C5—N4—H4 | 109.2 (13) | C25—C26—C21 | 120.50 (18) |
N4—C5—C6 | 110.20 (12) | C25—C26—H26 | 119.8 |
N4—C5—H5A | 109.6 | C21—C26—H26 | 119.8 |
C6—C5—H5A | 109.6 | O31—C31—C36 | 121.86 (13) |
N4—C5—H5B | 109.6 | O31—C31—C32 | 126.30 (14) |
C6—C5—H5B | 109.6 | C36—C31—C32 | 111.73 (12) |
H5A—C5—H5B | 108.1 | C33—C32—C31 | 123.34 (13) |
C5—C6—C7 | 111.73 (14) | C33—C32—N32 | 116.69 (13) |
C5—C6—H6A | 109.3 | C31—C32—N32 | 119.97 (13) |
C7—C6—H6A | 109.3 | C34—C33—C32 | 119.69 (13) |
C5—C6—H6B | 109.3 | C34—C33—H33 | 120.2 |
C7—C6—H6B | 109.3 | C32—C33—H33 | 120.2 |
H6A—C6—H6B | 107.9 | C33—C34—C35 | 121.50 (13) |
C6—C7—C2 | 111.04 (14) | C33—C34—N34 | 119.35 (13) |
C6—C7—H7A | 109.4 | C35—C34—N34 | 119.14 (13) |
C2—C7—H7A | 109.4 | C36—C35—C34 | 117.40 (14) |
C6—C7—H7B | 109.4 | C36—C35—H35 | 121.3 |
C2—C7—H7B | 109.4 | C34—C35—H35 | 121.3 |
H7A—C7—H7B | 108.0 | C35—C36—C31 | 126.25 (13) |
N4—C8—H8A | 109.5 | C35—C36—N36 | 117.55 (13) |
N4—C8—H8B | 109.5 | C31—C36—N36 | 116.16 (12) |
H8A—C8—H8B | 109.5 | O322—N32—O321 | 122.88 (13) |
N4—C8—H8C | 109.5 | O322—N32—C32 | 118.38 (12) |
H8A—C8—H8C | 109.5 | O321—N32—C32 | 118.72 (12) |
H8B—C8—H8C | 109.5 | O341—N34—O342 | 122.86 (12) |
C16—C11—C12 | 119.71 (19) | O341—N34—C34 | 118.82 (13) |
C16—C11—S1 | 120.98 (15) | O342—N34—C34 | 118.32 (12) |
C12—C11—S1 | 119.28 (13) | O361—N36—O362 | 123.81 (12) |
C13—C12—C11 | 118.75 (15) | O361—N36—C36 | 117.92 (12) |
C13—C12—N1 | 122.83 (15) | O362—N36—C36 | 118.27 (12) |
C11—C12—N1 | 118.42 (16) | | |
| | | |
C22—N1—C1—C2 | 147.93 (14) | C1—N1—C22—C23 | 17.3 (2) |
C12—N1—C1—C2 | −60.27 (18) | C12—N1—C22—C21 | 44.4 (2) |
N1—C1—C2—C3 | −55.39 (17) | C1—N1—C22—C21 | −163.41 (14) |
N1—C1—C2—C7 | −177.44 (13) | C21—C22—C23—C24 | 1.5 (2) |
C7—C2—C3—N4 | −57.81 (16) | N1—C22—C23—C24 | −179.12 (15) |
C1—C2—C3—N4 | −179.23 (11) | C22—C23—C24—C25 | −2.0 (3) |
C2—C3—N4—C8 | −174.63 (12) | C23—C24—C25—C26 | 0.0 (3) |
C2—C3—N4—C5 | 60.42 (15) | C24—C25—C26—C21 | 2.4 (3) |
C8—N4—C5—C6 | 176.30 (14) | C22—C21—C26—C25 | −2.9 (3) |
C3—N4—C5—C6 | −58.85 (16) | S1—C21—C26—C25 | 175.17 (14) |
N4—C5—C6—C7 | 55.17 (17) | O31—C31—C32—C33 | −174.09 (14) |
C5—C6—C7—C2 | −53.39 (18) | C36—C31—C32—C33 | 2.2 (2) |
C3—C2—C7—C6 | 54.29 (18) | O31—C31—C32—N32 | 6.2 (2) |
C1—C2—C7—C6 | 176.52 (14) | C36—C31—C32—N32 | −177.49 (13) |
C21—S1—C11—C16 | −146.03 (14) | C31—C32—C33—C34 | −3.5 (2) |
C21—S1—C11—C12 | 35.93 (14) | N32—C32—C33—C34 | 176.23 (13) |
C16—C11—C12—C13 | 2.2 (2) | C32—C33—C34—C35 | 3.1 (2) |
S1—C11—C12—C13 | −179.73 (12) | C32—C33—C34—N34 | −175.86 (13) |
C16—C11—C12—N1 | −177.34 (14) | C33—C34—C35—C36 | −1.6 (2) |
S1—C11—C12—N1 | 0.7 (2) | N34—C34—C35—C36 | 177.32 (13) |
C22—N1—C12—C13 | 133.74 (16) | C34—C35—C36—C31 | 0.5 (2) |
C1—N1—C12—C13 | −18.4 (2) | C34—C35—C36—N36 | 178.13 (12) |
C22—N1—C12—C11 | −46.7 (2) | O31—C31—C36—C35 | 175.76 (14) |
C1—N1—C12—C11 | 161.13 (14) | C32—C31—C36—C35 | −0.7 (2) |
C11—C12—C13—C14 | −2.8 (2) | O31—C31—C36—N36 | −1.9 (2) |
N1—C12—C13—C14 | 176.77 (14) | C32—C31—C36—N36 | −178.38 (12) |
C12—C13—C14—C15 | 1.1 (3) | C33—C32—N32—O322 | 26.6 (2) |
C13—C14—C15—C16 | 1.1 (3) | C31—C32—N32—O322 | −153.68 (13) |
C14—C15—C16—C11 | −1.6 (3) | C33—C32—N32—O321 | −151.69 (14) |
C12—C11—C16—C15 | −0.1 (3) | C31—C32—N32—O321 | 28.0 (2) |
S1—C11—C16—C15 | −178.09 (14) | C33—C34—N34—O341 | −14.8 (2) |
C11—S1—C21—C26 | 143.82 (15) | C35—C34—N34—O341 | 166.24 (13) |
C11—S1—C21—C22 | −38.10 (15) | C33—C34—N34—O342 | 165.15 (13) |
C26—C21—C22—C23 | 0.9 (2) | C35—C34—N34—O342 | −13.8 (2) |
S1—C21—C22—C23 | −177.19 (12) | C35—C36—N36—O361 | −58.59 (18) |
C26—C21—C22—N1 | −178.46 (15) | C31—C36—N36—O361 | 119.31 (15) |
S1—C21—C22—N1 | 3.4 (2) | C35—C36—N36—O362 | 121.21 (15) |
C12—N1—C22—C23 | −134.91 (16) | C31—C36—N36—O362 | −60.90 (18) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O31 | 0.89 (2) | 1.84 (2) | 2.6879 (17) | 158.2 (19) |
N4—H4···O321 | 0.89 (2) | 2.46 (2) | 3.0191 (17) | 121.8 (16) |
C3—H3B···O321 | 0.99 | 2.50 | 3.0790 (19) | 117 |
C5—H5B···O342i | 0.99 | 2.50 | 3.409 (2) | 152 |
C6—H6A···O362 | 0.99 | 2.47 | 3.419 (2) | 160 |
C6—H6B···O341ii | 0.99 | 2.56 | 3.4229 (19) | 146 |
C35—H35···O322iii | 0.95 | 2.52 | 3.4568 (19) | 168 |
Symmetry codes: (i) x−1, y−1, z; (ii) x, y−1, z; (iii) x+1, y, z. |