The title compound [systematic name: 10-[2-(diethylamino)propyl]phenothiazinium 2,4,6-trinitrophenolate], C
19H
25N
2S
+·C
6H
2N
3O
7−, is a pharmacologially active compound. The dihedral angle between the two outer aromatic rings of the phenothiazine unit is 38.64 (12)°. The crystal packing is stabilized by N—H
O hydrogen bonds and several weak C—H
O contacts. The molecular conformation of the cation does not change significantly when it is crystallized with chloride or perrhenate as the anion.
Supporting information
CCDC reference: 643084
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.005 Å
- R factor = 0.077
- wR factor = 0.212
- Data-to-parameter ratio = 12.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.89 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.43 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C4
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.18
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT410_ALERT_2_C Short Intra H...H Contact H1B .. H13 .. 1.97 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 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
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
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.
10-[2-(diethylamino)propyl]phenothiazinium 2,4,6-trinitrophenolate
top
Crystal data top
C19H25N2S+·C6H2N3O7− | F(000) = 2272 |
Mr = 541.58 | Dx = 1.435 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 17551 reflections |
a = 36.876 (3) Å | θ = 1.7–24.9° |
b = 8.4622 (4) Å | µ = 0.19 mm−1 |
c = 16.5727 (11) Å | T = 173 K |
β = 104.163 (6)° | Block, yellow |
V = 5014.3 (6) Å3 | 0.29 × 0.26 × 0.25 mm |
Z = 8 | |
Data collection top
Stoe IPDS-II two-circle diffractometer | 4421 independent reflections |
Radiation source: fine-focus sealed tube | 3505 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.081 |
ω scans | θmax = 25.0°, θmin = 2.5° |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −43→41 |
Tmin = 0.938, Tmax = 0.945 | k = −10→10 |
22001 measured reflections | l = −19→19 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.077 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.212 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.1318P)2 + 4.3473P] where P = (Fo2 + 2Fc2)/3 |
4421 reflections | (Δ/σ)max = 0.003 |
347 parameters | Δρmax = 0.46 e Å−3 |
0 restraints | Δρmin = −0.55 e Å−3 |
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 | 0.74108 (2) | 0.66325 (11) | 0.34506 (5) | 0.0550 (3) | |
N1 | 0.66355 (7) | 0.5356 (3) | 0.28311 (14) | 0.0427 (6) | |
N2 | 0.61333 (7) | 0.1462 (3) | 0.23512 (16) | 0.0452 (6) | |
H2 | 0.6000 (12) | 0.191 (5) | 0.184 (3) | 0.071 (12)* | |
C1 | 0.63169 (9) | 0.4282 (4) | 0.26719 (19) | 0.0441 (7) | |
H1A | 0.6145 | 0.4531 | 0.2128 | 0.053* | |
H1B | 0.6178 | 0.4403 | 0.3110 | 0.053* | |
C2 | 0.64592 (8) | 0.2587 (4) | 0.26678 (18) | 0.0428 (7) | |
H2A | 0.6623 | 0.2542 | 0.2269 | 0.051* | |
C3 | 0.66951 (10) | 0.2111 (4) | 0.3519 (2) | 0.0538 (8) | |
H3A | 0.6782 | 0.1021 | 0.3498 | 0.081* | |
H3B | 0.6544 | 0.2187 | 0.3929 | 0.081* | |
H3C | 0.6911 | 0.2818 | 0.3680 | 0.081* | |
C4 | 0.58716 (10) | 0.1387 (5) | 0.2930 (2) | 0.0597 (9) | |
H4A | 0.5997 | 0.0813 | 0.3443 | 0.072* | |
H4B | 0.5820 | 0.2475 | 0.3091 | 0.072* | |
C5 | 0.55072 (15) | 0.0581 (8) | 0.2542 (4) | 0.117 (2) | |
H5A | 0.5350 | 0.0559 | 0.2941 | 0.175* | |
H5B | 0.5556 | −0.0503 | 0.2389 | 0.175* | |
H5C | 0.5378 | 0.1162 | 0.2042 | 0.175* | |
C6 | 0.62604 (10) | −0.0177 (4) | 0.21878 (19) | 0.0503 (8) | |
H6A | 0.6038 | −0.0851 | 0.1980 | 0.060* | |
H6B | 0.6405 | −0.0635 | 0.2719 | 0.060* | |
C7 | 0.64982 (11) | −0.0205 (4) | 0.1563 (2) | 0.0554 (8) | |
H7A | 0.6572 | −0.1295 | 0.1485 | 0.083* | |
H7B | 0.6722 | 0.0442 | 0.1769 | 0.083* | |
H7C | 0.6354 | 0.0220 | 0.1031 | 0.083* | |
C11 | 0.70168 (9) | 0.7216 (4) | 0.38069 (18) | 0.0443 (7) | |
C12 | 0.66696 (9) | 0.6505 (3) | 0.34756 (16) | 0.0405 (6) | |
C13 | 0.63670 (9) | 0.6956 (4) | 0.37916 (17) | 0.0446 (7) | |
H13 | 0.6126 | 0.6520 | 0.3563 | 0.053* | |
C14 | 0.64170 (10) | 0.8048 (4) | 0.44429 (19) | 0.0505 (8) | |
H14 | 0.6211 | 0.8326 | 0.4664 | 0.061* | |
C15 | 0.67632 (10) | 0.8729 (4) | 0.47690 (19) | 0.0513 (8) | |
H15 | 0.6796 | 0.9460 | 0.5216 | 0.062* | |
C16 | 0.70612 (10) | 0.8335 (4) | 0.44386 (18) | 0.0475 (7) | |
H16 | 0.7297 | 0.8830 | 0.4644 | 0.057* | |
C21 | 0.71793 (9) | 0.6342 (4) | 0.23961 (19) | 0.0459 (7) | |
C22 | 0.68275 (8) | 0.5622 (3) | 0.21914 (17) | 0.0422 (7) | |
C23 | 0.66761 (9) | 0.5185 (4) | 0.13692 (18) | 0.0460 (7) | |
H23 | 0.6443 | 0.4650 | 0.1221 | 0.055* | |
C24 | 0.68683 (10) | 0.5534 (4) | 0.0760 (2) | 0.0525 (8) | |
H24 | 0.6766 | 0.5208 | 0.0202 | 0.063* | |
C25 | 0.72014 (11) | 0.6338 (4) | 0.0956 (2) | 0.0593 (9) | |
H25 | 0.7323 | 0.6616 | 0.0532 | 0.071* | |
C26 | 0.73591 (10) | 0.6742 (4) | 0.1781 (2) | 0.0568 (8) | |
H26 | 0.7591 | 0.7292 | 0.1924 | 0.068* | |
O31 | 0.58894 (6) | 0.6879 (3) | 0.58246 (13) | 0.0500 (6) | |
C31 | 0.56212 (9) | 0.6614 (4) | 0.52054 (18) | 0.0479 (7) | |
C32 | 0.53700 (10) | 0.7777 (5) | 0.4734 (2) | 0.0581 (9) | |
C33 | 0.50836 (10) | 0.7423 (6) | 0.4047 (2) | 0.0682 (12) | |
H33 | 0.4928 | 0.8240 | 0.3759 | 0.082* | |
C34 | 0.50253 (10) | 0.5873 (6) | 0.3781 (2) | 0.0654 (11) | |
C35 | 0.52634 (10) | 0.4675 (5) | 0.41689 (19) | 0.0601 (9) | |
H35 | 0.5232 | 0.3620 | 0.3968 | 0.072* | |
C36 | 0.55451 (9) | 0.5054 (4) | 0.48485 (18) | 0.0501 (8) | |
N32 | 0.54170 (9) | 0.9432 (4) | 0.4958 (2) | 0.0689 (9) | |
N34 | 0.47234 (10) | 0.5499 (8) | 0.3072 (2) | 0.0889 (14) | |
N36 | 0.57944 (8) | 0.3774 (3) | 0.52291 (16) | 0.0521 (7) | |
O321 | 0.55961 (9) | 0.9794 (3) | 0.5661 (2) | 0.0787 (8) | |
O322 | 0.52714 (8) | 1.0442 (4) | 0.4438 (2) | 0.0908 (11) | |
O341 | 0.45479 (9) | 0.6596 (6) | 0.26505 (18) | 0.1063 (15) | |
O342 | 0.46524 (9) | 0.4110 (7) | 0.2904 (2) | 0.1079 (14) | |
O361 | 0.59591 (8) | 0.3034 (3) | 0.47877 (16) | 0.0707 (7) | |
O362 | 0.58297 (7) | 0.3499 (3) | 0.59752 (14) | 0.0557 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0454 (5) | 0.0725 (6) | 0.0447 (5) | 0.0009 (4) | 0.0063 (4) | −0.0119 (4) |
N1 | 0.0476 (14) | 0.0444 (14) | 0.0375 (12) | −0.0022 (11) | 0.0130 (11) | −0.0040 (10) |
N2 | 0.0500 (15) | 0.0489 (15) | 0.0383 (13) | −0.0047 (11) | 0.0138 (12) | −0.0047 (11) |
C1 | 0.0454 (16) | 0.0471 (17) | 0.0398 (15) | −0.0018 (13) | 0.0101 (12) | −0.0031 (12) |
C2 | 0.0453 (16) | 0.0449 (17) | 0.0384 (14) | −0.0032 (13) | 0.0106 (12) | 0.0003 (12) |
C3 | 0.057 (2) | 0.0559 (19) | 0.0451 (17) | −0.0004 (15) | 0.0067 (15) | 0.0097 (14) |
C4 | 0.058 (2) | 0.075 (2) | 0.0529 (19) | −0.0199 (17) | 0.0266 (16) | −0.0190 (17) |
C5 | 0.081 (3) | 0.170 (6) | 0.120 (4) | −0.065 (4) | 0.062 (3) | −0.090 (4) |
C6 | 0.069 (2) | 0.0420 (17) | 0.0424 (16) | −0.0032 (15) | 0.0182 (15) | −0.0013 (13) |
C7 | 0.072 (2) | 0.0469 (18) | 0.0516 (18) | 0.0061 (16) | 0.0234 (17) | 0.0022 (14) |
C11 | 0.0530 (18) | 0.0426 (16) | 0.0352 (14) | 0.0022 (13) | 0.0066 (12) | 0.0012 (12) |
C12 | 0.0498 (16) | 0.0405 (15) | 0.0292 (13) | 0.0021 (12) | 0.0060 (12) | 0.0034 (11) |
C13 | 0.0532 (18) | 0.0427 (16) | 0.0375 (15) | 0.0023 (13) | 0.0103 (13) | 0.0057 (12) |
C14 | 0.065 (2) | 0.0504 (18) | 0.0391 (15) | 0.0053 (15) | 0.0182 (15) | 0.0019 (13) |
C15 | 0.070 (2) | 0.0467 (17) | 0.0386 (15) | −0.0002 (15) | 0.0155 (15) | −0.0009 (13) |
C16 | 0.0563 (18) | 0.0465 (17) | 0.0365 (14) | −0.0017 (14) | 0.0054 (13) | −0.0005 (12) |
C21 | 0.0472 (17) | 0.0502 (17) | 0.0406 (15) | −0.0003 (13) | 0.0110 (13) | −0.0057 (13) |
C22 | 0.0485 (16) | 0.0418 (16) | 0.0378 (14) | 0.0033 (13) | 0.0132 (12) | −0.0013 (12) |
C23 | 0.0535 (18) | 0.0444 (17) | 0.0394 (15) | 0.0018 (13) | 0.0101 (13) | −0.0024 (12) |
C24 | 0.066 (2) | 0.0523 (18) | 0.0402 (16) | 0.0018 (16) | 0.0147 (15) | −0.0022 (14) |
C25 | 0.069 (2) | 0.066 (2) | 0.0502 (18) | −0.0036 (18) | 0.0288 (17) | −0.0046 (16) |
C26 | 0.0534 (19) | 0.067 (2) | 0.0535 (19) | −0.0064 (16) | 0.0204 (16) | −0.0075 (16) |
O31 | 0.0513 (13) | 0.0556 (13) | 0.0393 (11) | −0.0017 (10) | 0.0039 (10) | 0.0045 (9) |
C31 | 0.0445 (17) | 0.062 (2) | 0.0364 (15) | −0.0057 (14) | 0.0085 (13) | 0.0118 (13) |
C32 | 0.0493 (19) | 0.072 (2) | 0.0513 (18) | −0.0073 (16) | 0.0099 (15) | 0.0249 (17) |
C33 | 0.0452 (19) | 0.111 (3) | 0.0456 (19) | −0.010 (2) | 0.0058 (15) | 0.032 (2) |
C34 | 0.0467 (19) | 0.114 (3) | 0.0335 (16) | −0.015 (2) | 0.0067 (14) | 0.0107 (19) |
C35 | 0.0517 (19) | 0.095 (3) | 0.0344 (15) | −0.0158 (19) | 0.0131 (14) | −0.0032 (16) |
C36 | 0.0489 (17) | 0.066 (2) | 0.0356 (15) | −0.0079 (15) | 0.0111 (13) | 0.0048 (14) |
N32 | 0.0534 (17) | 0.071 (2) | 0.077 (2) | −0.0043 (15) | 0.0071 (16) | 0.0368 (18) |
N34 | 0.0479 (19) | 0.185 (5) | 0.0326 (16) | −0.015 (3) | 0.0079 (14) | 0.002 (2) |
N36 | 0.0546 (16) | 0.0591 (17) | 0.0417 (14) | −0.0094 (13) | 0.0101 (12) | −0.0048 (12) |
O321 | 0.0767 (19) | 0.0561 (16) | 0.090 (2) | 0.0013 (13) | −0.0049 (16) | 0.0175 (14) |
O322 | 0.0670 (18) | 0.093 (2) | 0.105 (2) | −0.0008 (15) | 0.0071 (16) | 0.0649 (19) |
O341 | 0.0587 (17) | 0.212 (5) | 0.0421 (15) | −0.009 (2) | 0.0003 (13) | 0.032 (2) |
O342 | 0.0620 (19) | 0.194 (4) | 0.0610 (19) | −0.015 (2) | 0.0019 (15) | −0.038 (2) |
O361 | 0.0749 (17) | 0.0812 (19) | 0.0587 (15) | 0.0031 (14) | 0.0218 (13) | −0.0149 (13) |
O362 | 0.0672 (15) | 0.0579 (14) | 0.0405 (12) | −0.0047 (11) | 0.0104 (10) | 0.0035 (10) |
Geometric parameters (Å, º) top
S1—C21 | 1.764 (3) | C14—C15 | 1.384 (5) |
S1—C11 | 1.767 (3) | C14—H14 | 0.9500 |
N1—C12 | 1.426 (4) | C15—C16 | 1.383 (5) |
N1—C22 | 1.429 (4) | C15—H15 | 0.9500 |
N1—C1 | 1.458 (4) | C16—H16 | 0.9500 |
N2—C6 | 1.509 (4) | C21—C26 | 1.387 (4) |
N2—C4 | 1.519 (4) | C21—C22 | 1.398 (4) |
N2—C2 | 1.523 (4) | C22—C23 | 1.390 (4) |
N2—H2 | 0.95 (5) | C23—C24 | 1.400 (4) |
C1—C2 | 1.528 (4) | C23—H23 | 0.9500 |
C1—H1A | 0.9900 | C24—C25 | 1.372 (5) |
C1—H1B | 0.9900 | C24—H24 | 0.9500 |
C2—C3 | 1.520 (4) | C25—C26 | 1.392 (5) |
C2—H2A | 1.0000 | C25—H25 | 0.9500 |
C3—H3A | 0.9800 | C26—H26 | 0.9500 |
C3—H3B | 0.9800 | O31—C31 | 1.259 (4) |
C3—H3C | 0.9800 | C31—C32 | 1.443 (5) |
C4—C5 | 1.504 (6) | C31—C36 | 1.445 (5) |
C4—H4A | 0.9900 | C32—C33 | 1.383 (5) |
C4—H4B | 0.9900 | C32—N32 | 1.448 (6) |
C5—H5A | 0.9800 | C33—C34 | 1.384 (6) |
C5—H5B | 0.9800 | C33—H33 | 0.9500 |
C5—H5C | 0.9800 | C34—C35 | 1.391 (6) |
C6—C7 | 1.511 (4) | C34—N34 | 1.442 (5) |
C6—H6A | 0.9900 | C35—C36 | 1.371 (5) |
C6—H6B | 0.9900 | C35—H35 | 0.9500 |
C7—H7A | 0.9800 | C36—N36 | 1.460 (5) |
C7—H7B | 0.9800 | N32—O321 | 1.228 (5) |
C7—H7C | 0.9800 | N32—O322 | 1.239 (4) |
C11—C16 | 1.391 (4) | N34—O342 | 1.222 (6) |
C11—C12 | 1.400 (5) | N34—O341 | 1.244 (6) |
C12—C13 | 1.397 (4) | N36—O361 | 1.231 (4) |
C13—C14 | 1.398 (4) | N36—O362 | 1.233 (3) |
C13—H13 | 0.9500 | | |
| | | |
C21—S1—C11 | 97.58 (14) | C12—C13—C14 | 120.2 (3) |
C12—N1—C22 | 118.7 (2) | C12—C13—H13 | 119.9 |
C12—N1—C1 | 118.7 (2) | C14—C13—H13 | 119.9 |
C22—N1—C1 | 119.2 (2) | C15—C14—C13 | 120.7 (3) |
C6—N2—C4 | 110.4 (3) | C15—C14—H14 | 119.6 |
C6—N2—C2 | 112.5 (2) | C13—C14—H14 | 119.6 |
C4—N2—C2 | 112.2 (2) | C14—C15—C16 | 119.4 (3) |
C6—N2—H2 | 108 (2) | C14—C15—H15 | 120.3 |
C4—N2—H2 | 108 (3) | C16—C15—H15 | 120.3 |
C2—N2—H2 | 105 (3) | C15—C16—C11 | 120.2 (3) |
N1—C1—C2 | 108.9 (2) | C15—C16—H16 | 119.9 |
N1—C1—H1A | 109.9 | C11—C16—H16 | 119.9 |
C2—C1—H1A | 109.9 | C26—C21—C22 | 120.7 (3) |
N1—C1—H1B | 109.9 | C26—C21—S1 | 119.4 (3) |
C2—C1—H1B | 109.9 | C22—C21—S1 | 119.8 (2) |
H1A—C1—H1B | 108.3 | C23—C22—C21 | 118.7 (3) |
C3—C2—N2 | 112.2 (3) | C23—C22—N1 | 122.1 (3) |
C3—C2—C1 | 111.3 (3) | C21—C22—N1 | 119.2 (3) |
N2—C2—C1 | 110.2 (2) | C22—C23—C24 | 119.9 (3) |
C3—C2—H2A | 107.6 | C22—C23—H23 | 120.1 |
N2—C2—H2A | 107.6 | C24—C23—H23 | 120.1 |
C1—C2—H2A | 107.6 | C25—C24—C23 | 121.1 (3) |
C2—C3—H3A | 109.5 | C25—C24—H24 | 119.5 |
C2—C3—H3B | 109.5 | C23—C24—H24 | 119.5 |
H3A—C3—H3B | 109.5 | C24—C25—C26 | 119.3 (3) |
C2—C3—H3C | 109.5 | C24—C25—H25 | 120.4 |
H3A—C3—H3C | 109.5 | C26—C25—H25 | 120.4 |
H3B—C3—H3C | 109.5 | C21—C26—C25 | 120.2 (3) |
C5—C4—N2 | 112.8 (3) | C21—C26—H26 | 119.9 |
C5—C4—H4A | 109.0 | C25—C26—H26 | 119.9 |
N2—C4—H4A | 109.0 | O31—C31—C32 | 126.3 (3) |
C5—C4—H4B | 109.0 | O31—C31—C36 | 122.1 (3) |
N2—C4—H4B | 109.0 | C32—C31—C36 | 111.5 (3) |
H4A—C4—H4B | 107.8 | C33—C32—C31 | 123.9 (4) |
C4—C5—H5A | 109.5 | C33—C32—N32 | 116.1 (3) |
C4—C5—H5B | 109.5 | C31—C32—N32 | 120.0 (3) |
H5A—C5—H5B | 109.5 | C32—C33—C34 | 119.7 (4) |
C4—C5—H5C | 109.5 | C32—C33—H33 | 120.1 |
H5A—C5—H5C | 109.5 | C34—C33—H33 | 120.1 |
H5B—C5—H5C | 109.5 | C33—C34—C35 | 120.8 (3) |
N2—C6—C7 | 113.3 (3) | C33—C34—N34 | 119.8 (4) |
N2—C6—H6A | 108.9 | C35—C34—N34 | 119.4 (5) |
C7—C6—H6A | 108.9 | C36—C35—C34 | 118.4 (4) |
N2—C6—H6B | 108.9 | C36—C35—H35 | 120.8 |
C7—C6—H6B | 108.9 | C34—C35—H35 | 120.8 |
H6A—C6—H6B | 107.7 | C35—C36—C31 | 125.6 (3) |
C6—C7—H7A | 109.5 | C35—C36—N36 | 116.8 (3) |
C6—C7—H7B | 109.5 | C31—C36—N36 | 117.5 (3) |
H7A—C7—H7B | 109.5 | O321—N32—O322 | 121.9 (4) |
C6—C7—H7C | 109.5 | O321—N32—C32 | 119.2 (3) |
H7A—C7—H7C | 109.5 | O322—N32—C32 | 119.0 (4) |
H7B—C7—H7C | 109.5 | O342—N34—O341 | 122.5 (4) |
C16—C11—C12 | 121.0 (3) | O342—N34—C34 | 118.5 (5) |
C16—C11—S1 | 119.1 (2) | O341—N34—C34 | 119.1 (5) |
C12—C11—S1 | 119.8 (2) | O361—N36—O362 | 123.6 (3) |
C13—C12—C11 | 118.2 (3) | O361—N36—C36 | 118.1 (3) |
C13—C12—N1 | 122.3 (3) | O362—N36—C36 | 118.3 (3) |
C11—C12—N1 | 119.4 (3) | | |
| | | |
C12—N1—C1—C2 | −128.8 (3) | C12—N1—C22—C21 | 36.2 (4) |
C22—N1—C1—C2 | 72.6 (3) | C1—N1—C22—C21 | −165.2 (3) |
C6—N2—C2—C3 | −65.5 (3) | C21—C22—C23—C24 | −2.9 (5) |
C4—N2—C2—C3 | 59.7 (4) | N1—C22—C23—C24 | 177.2 (3) |
C6—N2—C2—C1 | 169.7 (2) | C22—C23—C24—C25 | −1.6 (5) |
C4—N2—C2—C1 | −65.0 (3) | C23—C24—C25—C26 | 3.3 (5) |
N1—C1—C2—C3 | 64.9 (3) | C22—C21—C26—C25 | −4.1 (5) |
N1—C1—C2—N2 | −169.8 (2) | S1—C21—C26—C25 | 171.9 (3) |
C6—N2—C4—C5 | −66.5 (5) | C24—C25—C26—C21 | −0.4 (6) |
C2—N2—C4—C5 | 167.1 (4) | O31—C31—C32—C33 | 178.7 (3) |
C4—N2—C6—C7 | 175.6 (3) | C36—C31—C32—C33 | 2.4 (4) |
C2—N2—C6—C7 | −58.2 (4) | O31—C31—C32—N32 | 0.4 (5) |
C21—S1—C11—C16 | −145.7 (3) | C36—C31—C32—N32 | −175.8 (3) |
C21—S1—C11—C12 | 36.8 (3) | C31—C32—C33—C34 | 0.3 (5) |
C16—C11—C12—C13 | 0.5 (4) | N32—C32—C33—C34 | 178.6 (3) |
S1—C11—C12—C13 | 177.9 (2) | C32—C33—C34—C35 | −3.4 (5) |
C16—C11—C12—N1 | −179.7 (3) | C32—C33—C34—N34 | 179.1 (3) |
S1—C11—C12—N1 | −2.3 (4) | C33—C34—C35—C36 | 3.4 (5) |
C22—N1—C12—C13 | 139.6 (3) | N34—C34—C35—C36 | −179.1 (3) |
C1—N1—C12—C13 | −19.1 (4) | C34—C35—C36—C31 | −0.3 (5) |
C22—N1—C12—C11 | −40.2 (4) | C34—C35—C36—N36 | −178.7 (3) |
C1—N1—C12—C11 | 161.1 (3) | O31—C31—C36—C35 | −178.9 (3) |
C11—C12—C13—C14 | −2.3 (4) | C32—C31—C36—C35 | −2.4 (4) |
N1—C12—C13—C14 | 177.8 (3) | O31—C31—C36—N36 | −0.5 (4) |
C12—C13—C14—C15 | 1.7 (5) | C32—C31—C36—N36 | 176.0 (3) |
C13—C14—C15—C16 | 0.8 (5) | C33—C32—N32—O321 | 161.8 (3) |
C14—C15—C16—C11 | −2.6 (5) | C31—C32—N32—O321 | −19.8 (5) |
C12—C11—C16—C15 | 2.0 (5) | C33—C32—N32—O322 | −17.4 (5) |
S1—C11—C16—C15 | −175.4 (2) | C31—C32—N32—O322 | 161.0 (3) |
C11—S1—C21—C26 | 143.3 (3) | C33—C34—N34—O342 | −172.3 (3) |
C11—S1—C21—C22 | −40.7 (3) | C35—C34—N34—O342 | 10.2 (5) |
C26—C21—C22—C23 | 5.7 (5) | C33—C34—N34—O341 | 8.5 (5) |
S1—C21—C22—C23 | −170.2 (2) | C35—C34—N34—O341 | −169.0 (3) |
C26—C21—C22—N1 | −174.4 (3) | C35—C36—N36—O361 | 56.4 (4) |
S1—C21—C22—N1 | 9.7 (4) | C31—C36—N36—O361 | −122.1 (3) |
C12—N1—C22—C23 | −143.9 (3) | C35—C36—N36—O362 | −123.9 (3) |
C1—N1—C22—C23 | 14.7 (4) | C31—C36—N36—O362 | 57.6 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O31i | 0.95 (5) | 1.92 (5) | 2.841 (4) | 161 (4) |
C1—H1A···O31i | 0.99 | 2.45 | 3.234 (4) | 136 |
C23—H23···O31i | 0.95 | 2.37 | 3.316 (4) | 175 |
Symmetry code: (i) x, −y+1, z−1/2. |