The title compound, C
12H
16N
4OS, is zwitterionic and exists in the
EZ configuration of thiosemicarbazones. The thiocarbonyl S atom and coordinating pyridyl N atom are aligned
cis to each other, avoiding the possibility of a structural reorientation upon coordination. Two crystallographically independent molecules,
A and
B, are observed in the asymmetric unit, with the morpholyl ring adopting a chair conformation in both molecules. N—H
N and N—H
S intramolecular hydrogen bonds are observed in the molecular structure, generating four rings of motif
R12(5). There is zigzag packing in the unit cell, involving both intra- and intermolecular hydrogen-bonding interactions.
Supporting information
CCDC reference: 249048
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.044
- wR factor = 0.125
- Data-to-parameter ratio = 16.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.64 mm
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 22
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
4-morpholinyl{2-[1-(2-pyridinyl)ethylidene]diazan-2-iumylidene}methanethiolate
top
Crystal data top
C12H16N4OS | F(000) = 1120 |
Mr = 264.35 | Dx = 1.323 Mg m−3 |
Monoclinic, P21/c | Melting point: 461 K K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 14.158 (9) Å | Cell parameters from 14456 reflections |
b = 11.075 (7) Å | θ = 2.2–26.5° |
c = 17.877 (1) Å | µ = 0.24 mm−1 |
β = 108.776 (1)° | T = 293 K |
V = 2654 (2) Å3 | Rod, yellow |
Z = 8 | 0.64 × 0.44 × 0.40 mm |
Data collection top
Siemens SMART CCD area-detector diffractometer | 5503 independent reflections |
Radiation source: fine-focus sealed tube | 4012 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
Detector resolution: 8.33 pixels mm-1 | θmax = 26.5°, θmin = 2.2° |
ω scans | h = −12→17 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −13→13 |
Tmin = 0.882, Tmax = 0.909 | l = −22→22 |
14456 measured reflections | |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.125 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0543P)2 + 1.0486P] where P = (Fo2 + 2Fc2)/3 |
5503 reflections | (Δ/σ)max = 0.001 |
335 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.21 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 | |
S1A | 0.39687 (4) | 0.26810 (5) | 0.20884 (3) | 0.04550 (16) | |
O1A | 0.10742 (14) | 0.0876 (2) | 0.28912 (13) | 0.0934 (7) | |
N1A | 0.29837 (13) | 0.17134 (18) | 0.29958 (11) | 0.0508 (5) | |
N2A | 0.45951 (12) | 0.11157 (15) | 0.33232 (9) | 0.0407 (4) | |
N3A | 0.54316 (12) | 0.11623 (15) | 0.31170 (10) | 0.0387 (4) | |
N4A | 0.68515 (14) | 0.1335 (2) | 0.24724 (11) | 0.0577 (5) | |
C1A | 0.28327 (19) | 0.0916 (3) | 0.35979 (15) | 0.0692 (8) | |
H1AA | 0.2753 | 0.1394 | 0.4028 | 0.083* | |
H1AB | 0.3411 | 0.0400 | 0.3809 | 0.083* | |
C2A | 0.1933 (2) | 0.0165 (3) | 0.32480 (19) | 0.0820 (9) | |
H2AB | 0.2046 | −0.0368 | 0.2854 | 0.098* | |
H2AC | 0.1820 | −0.0332 | 0.3657 | 0.098* | |
C3A | 0.1231 (2) | 0.1599 (3) | 0.22851 (18) | 0.0861 (10) | |
H3AB | 0.0638 | 0.2076 | 0.2037 | 0.103* | |
H3AC | 0.1343 | 0.1080 | 0.1885 | 0.103* | |
C4A | 0.20991 (18) | 0.2417 (2) | 0.26005 (16) | 0.0629 (7) | |
H4AB | 0.2204 | 0.2875 | 0.2172 | 0.075* | |
H4AC | 0.1969 | 0.2982 | 0.2970 | 0.075* | |
C5A | 0.38544 (15) | 0.17921 (18) | 0.28386 (11) | 0.0384 (4) | |
C6A | 0.62836 (15) | 0.06946 (18) | 0.35242 (11) | 0.0411 (5) | |
C7A | 0.70958 (15) | 0.08118 (19) | 0.31852 (12) | 0.0447 (5) | |
C8A | 0.75752 (19) | 0.1475 (3) | 0.21519 (16) | 0.0703 (8) | |
H8AA | 0.7414 | 0.1844 | 0.1659 | 0.084* | |
C9A | 0.85421 (19) | 0.1109 (3) | 0.25048 (18) | 0.0710 (8) | |
H9AA | 0.9021 | 0.1231 | 0.2258 | 0.085* | |
C10A | 0.87865 (18) | 0.0562 (2) | 0.32266 (19) | 0.0690 (8) | |
H10A | 0.9434 | 0.0295 | 0.3478 | 0.083* | |
C11A | 0.80535 (17) | 0.0409 (2) | 0.35791 (15) | 0.0571 (6) | |
H11A | 0.8202 | 0.0043 | 0.4072 | 0.069* | |
C12A | 0.63955 (18) | 0.0109 (2) | 0.42936 (13) | 0.0557 (6) | |
H12A | 0.5780 | 0.0174 | 0.4409 | 0.084* | |
H12B | 0.6918 | 0.0502 | 0.4702 | 0.084* | |
H12C | 0.6561 | −0.0727 | 0.4268 | 0.084* | |
S1B | 0.90197 (4) | 0.30078 (6) | 0.06077 (4) | 0.05760 (19) | |
O1B | 1.17114 (13) | 0.1265 (2) | −0.04934 (12) | 0.0842 (6) | |
N1B | 0.98901 (13) | 0.21700 (19) | −0.04151 (11) | 0.0550 (5) | |
N2B | 0.82661 (12) | 0.16472 (16) | −0.07177 (10) | 0.0420 (4) | |
N3B | 0.74437 (12) | 0.17228 (16) | −0.04903 (10) | 0.0393 (4) | |
N4B | 0.60177 (13) | 0.20605 (18) | 0.01424 (11) | 0.0512 (5) | |
C1B | 0.99540 (18) | 0.1563 (3) | −0.11241 (14) | 0.0615 (7) | |
H1BA | 1.0055 | 0.2157 | −0.1490 | 0.074* | |
H1BB | 0.9335 | 0.1141 | −0.1383 | 0.074* | |
C2B | 1.0795 (2) | 0.0691 (3) | −0.09086 (18) | 0.0743 (8) | |
H2BB | 1.0661 | 0.0058 | −0.0581 | 0.089* | |
H2BC | 1.0849 | 0.0320 | −0.1385 | 0.089* | |
C3B | 1.1634 (2) | 0.1789 (4) | 0.02070 (19) | 0.0902 (10) | |
H3BB | 1.2266 | 0.2158 | 0.0500 | 0.108* | |
H3BC | 1.1495 | 0.1161 | 0.0535 | 0.108* | |
C4B | 1.08381 (18) | 0.2710 (3) | 0.00372 (18) | 0.0721 (8) | |
H4BB | 1.0793 | 0.3035 | 0.0529 | 0.087* | |
H4BC | 1.0995 | 0.3369 | −0.0261 | 0.087* | |
C5B | 0.90503 (15) | 0.22363 (19) | −0.02149 (12) | 0.0427 (5) | |
C6B | 0.65781 (15) | 0.12941 (18) | −0.08907 (12) | 0.0398 (5) | |
C7B | 0.57717 (15) | 0.14549 (19) | −0.05456 (12) | 0.0410 (5) | |
C8B | 0.53107 (19) | 0.2214 (3) | 0.04734 (15) | 0.0625 (7) | |
H8BA | 0.5475 | 0.2628 | 0.0951 | 0.075* | |
C9B | 0.43502 (19) | 0.1797 (3) | 0.01510 (16) | 0.0645 (7) | |
H9BA | 0.3880 | 0.1930 | 0.0405 | 0.077* | |
C10B | 0.40996 (17) | 0.1186 (2) | −0.05488 (15) | 0.0592 (7) | |
H10B | 0.3454 | 0.0897 | −0.0780 | 0.071* | |
C11B | 0.48176 (16) | 0.1000 (2) | −0.09114 (14) | 0.0503 (5) | |
H11B | 0.4666 | 0.0582 | −0.1387 | 0.060* | |
C12B | 0.64354 (17) | 0.0688 (2) | −0.16558 (13) | 0.0556 (6) | |
H12D | 0.6976 | 0.0894 | −0.1847 | 0.083* | |
H12E | 0.5816 | 0.0946 | −0.2031 | 0.083* | |
H12F | 0.6422 | −0.0171 | −0.1587 | 0.083* | |
H2N3 | 0.7519 (16) | 0.209 (2) | −0.0052 (13) | 0.045 (6)* | |
H1N3 | 0.5405 (17) | 0.155 (2) | 0.2671 (14) | 0.056 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1A | 0.0454 (3) | 0.0494 (3) | 0.0426 (3) | −0.0008 (2) | 0.0155 (2) | 0.0101 (2) |
O1A | 0.0485 (11) | 0.137 (2) | 0.0982 (15) | −0.0127 (12) | 0.0285 (10) | 0.0398 (14) |
N1A | 0.0380 (10) | 0.0641 (12) | 0.0514 (10) | 0.0004 (9) | 0.0161 (8) | 0.0168 (9) |
N2A | 0.0395 (9) | 0.0448 (10) | 0.0380 (9) | −0.0007 (7) | 0.0130 (7) | 0.0035 (7) |
N3A | 0.0390 (9) | 0.0400 (10) | 0.0360 (9) | −0.0020 (7) | 0.0106 (7) | −0.0011 (7) |
N4A | 0.0429 (11) | 0.0801 (15) | 0.0512 (11) | 0.0004 (10) | 0.0163 (9) | 0.0021 (10) |
C1A | 0.0554 (15) | 0.094 (2) | 0.0632 (15) | −0.0014 (14) | 0.0266 (12) | 0.0300 (15) |
C2A | 0.076 (2) | 0.091 (2) | 0.091 (2) | −0.0123 (17) | 0.0432 (17) | 0.0271 (18) |
C3A | 0.0453 (15) | 0.129 (3) | 0.0785 (19) | −0.0063 (16) | 0.0116 (14) | 0.0319 (19) |
C4A | 0.0474 (14) | 0.0714 (17) | 0.0744 (17) | 0.0120 (12) | 0.0260 (12) | 0.0203 (14) |
C5A | 0.0401 (11) | 0.0382 (11) | 0.0363 (10) | −0.0045 (8) | 0.0114 (8) | −0.0026 (8) |
C6A | 0.0434 (11) | 0.0359 (11) | 0.0402 (11) | 0.0008 (9) | 0.0083 (9) | −0.0050 (8) |
C7A | 0.0395 (11) | 0.0421 (12) | 0.0487 (12) | 0.0003 (9) | 0.0089 (9) | −0.0100 (10) |
C8A | 0.0541 (16) | 0.100 (2) | 0.0628 (16) | −0.0060 (14) | 0.0268 (13) | −0.0076 (15) |
C9A | 0.0468 (15) | 0.086 (2) | 0.086 (2) | −0.0115 (13) | 0.0300 (14) | −0.0316 (17) |
C10A | 0.0389 (13) | 0.0660 (17) | 0.097 (2) | 0.0043 (12) | 0.0145 (14) | −0.0237 (16) |
C11A | 0.0446 (13) | 0.0509 (14) | 0.0681 (15) | 0.0049 (11) | 0.0074 (11) | −0.0073 (11) |
C12A | 0.0607 (15) | 0.0535 (14) | 0.0485 (13) | 0.0083 (11) | 0.0116 (11) | 0.0062 (11) |
S1B | 0.0470 (3) | 0.0720 (4) | 0.0531 (3) | 0.0014 (3) | 0.0152 (3) | −0.0234 (3) |
O1B | 0.0459 (10) | 0.1226 (18) | 0.0907 (14) | 0.0138 (11) | 0.0314 (10) | −0.0125 (13) |
N1B | 0.0356 (10) | 0.0696 (13) | 0.0604 (11) | −0.0012 (9) | 0.0162 (9) | −0.0232 (10) |
N2B | 0.0357 (9) | 0.0478 (10) | 0.0439 (9) | 0.0011 (8) | 0.0147 (7) | −0.0067 (8) |
N3B | 0.0375 (9) | 0.0419 (10) | 0.0396 (9) | 0.0036 (7) | 0.0138 (8) | −0.0022 (8) |
N4B | 0.0456 (11) | 0.0600 (12) | 0.0514 (11) | 0.0024 (9) | 0.0203 (9) | −0.0020 (9) |
C1B | 0.0488 (14) | 0.0805 (18) | 0.0597 (14) | 0.0007 (12) | 0.0239 (12) | −0.0164 (13) |
C2B | 0.0740 (19) | 0.0750 (19) | 0.0874 (19) | 0.0105 (15) | 0.0449 (16) | −0.0100 (16) |
C3B | 0.0415 (15) | 0.144 (3) | 0.082 (2) | 0.0048 (17) | 0.0163 (14) | −0.020 (2) |
C4B | 0.0448 (14) | 0.088 (2) | 0.0853 (19) | −0.0174 (13) | 0.0239 (13) | −0.0310 (16) |
C5B | 0.0392 (11) | 0.0434 (12) | 0.0449 (11) | 0.0071 (9) | 0.0127 (9) | −0.0016 (9) |
C6B | 0.0381 (11) | 0.0366 (11) | 0.0425 (11) | 0.0033 (9) | 0.0100 (9) | 0.0028 (9) |
C7B | 0.0386 (11) | 0.0397 (11) | 0.0447 (11) | 0.0061 (9) | 0.0132 (9) | 0.0101 (9) |
C8B | 0.0579 (15) | 0.0782 (18) | 0.0595 (14) | 0.0086 (13) | 0.0300 (12) | −0.0010 (13) |
C9B | 0.0491 (14) | 0.0791 (19) | 0.0754 (18) | 0.0148 (13) | 0.0340 (13) | 0.0197 (15) |
C10B | 0.0380 (12) | 0.0686 (17) | 0.0702 (16) | 0.0040 (11) | 0.0161 (11) | 0.0246 (13) |
C11B | 0.0410 (12) | 0.0531 (14) | 0.0533 (13) | 0.0019 (10) | 0.0104 (10) | 0.0137 (10) |
C12B | 0.0495 (13) | 0.0619 (15) | 0.0534 (13) | −0.0002 (11) | 0.0140 (11) | −0.0149 (11) |
Geometric parameters (Å, º) top
S1A—C5A | 1.713 (2) | S1B—C5B | 1.713 (2) |
O1A—C2A | 1.416 (4) | O1B—C3B | 1.416 (3) |
O1A—C3A | 1.422 (3) | O1B—C2B | 1.421 (3) |
N1A—C5A | 1.353 (3) | N1B—C5B | 1.350 (3) |
N1A—C4A | 1.451 (3) | N1B—C4B | 1.454 (3) |
N1A—C1A | 1.460 (3) | N1B—C1B | 1.463 (3) |
N2A—N3A | 1.350 (2) | N2B—C5B | 1.350 (3) |
N2A—C5A | 1.352 (2) | N2B—N3B | 1.354 (2) |
N3A—C6A | 1.299 (2) | N3B—C6B | 1.294 (3) |
N3A—H1N3 | 0.90 (2) | N3B—H2N3 | 0.86 (2) |
N4A—C8A | 1.334 (3) | N4B—C8B | 1.328 (3) |
N4A—C7A | 1.340 (3) | N4B—C7B | 1.345 (3) |
C1A—C2A | 1.480 (4) | C1B—C2B | 1.484 (4) |
C1A—H1AA | 0.9700 | C1B—H1BA | 0.9700 |
C1A—H1AB | 0.9700 | C1B—H1BB | 0.9700 |
C2A—H2AB | 0.9700 | C2B—H2BB | 0.9700 |
C2A—H2AC | 0.9700 | C2B—H2BC | 0.9700 |
C3A—C4A | 1.484 (4) | C3B—C4B | 1.477 (4) |
C3A—H3AB | 0.9700 | C3B—H3BB | 0.9700 |
C3A—H3AC | 0.9700 | C3B—H3BC | 0.9700 |
C4A—H4AB | 0.9700 | C4B—H4BB | 0.9700 |
C4A—H4AC | 0.9700 | C4B—H4BC | 0.9700 |
C6A—C7A | 1.468 (3) | C6B—C7B | 1.473 (3) |
C6A—C12A | 1.482 (3) | C6B—C12B | 1.478 (3) |
C7A—C11A | 1.385 (3) | C7B—C11B | 1.392 (3) |
C8A—C9A | 1.371 (4) | C8B—C9B | 1.375 (4) |
C8A—H8AA | 0.9300 | C8B—H8BA | 0.9300 |
C9A—C10A | 1.366 (4) | C9B—C10B | 1.365 (4) |
C9A—H9AA | 0.9300 | C9B—H9BA | 0.9300 |
C10A—C11A | 1.387 (4) | C10B—C11B | 1.386 (3) |
C10A—H10A | 0.9300 | C10B—H10B | 0.9300 |
C11A—H11A | 0.9300 | C11B—H11B | 0.9300 |
C12A—H12A | 0.9600 | C12B—H12D | 0.9600 |
C12A—H12B | 0.9600 | C12B—H12E | 0.9600 |
C12A—H12C | 0.9600 | C12B—H12F | 0.9600 |
| | | |
C2A—O1A—C3A | 109.5 (2) | C3B—O1B—C2B | 109.1 (2) |
C5A—N1A—C4A | 124.46 (18) | C5B—N1B—C4B | 124.36 (19) |
C5A—N1A—C1A | 123.48 (19) | C5B—N1B—C1B | 124.07 (19) |
C4A—N1A—C1A | 112.06 (18) | C4B—N1B—C1B | 111.56 (18) |
N3A—N2A—C5A | 111.83 (16) | C5B—N2B—N3B | 111.87 (16) |
C6A—N3A—N2A | 124.73 (18) | C6B—N3B—N2B | 124.35 (18) |
C6A—N3A—H1N3 | 117.1 (15) | C6B—N3B—H2N3 | 119.7 (15) |
N2A—N3A—H1N3 | 118.1 (15) | N2B—N3B—H2N3 | 115.9 (15) |
C8A—N4A—C7A | 117.4 (2) | C8B—N4B—C7B | 117.5 (2) |
N1A—C1A—C2A | 109.8 (2) | N1B—C1B—C2B | 110.0 (2) |
N1A—C1A—H1AA | 109.7 | N1B—C1B—H1BA | 109.7 |
C2A—C1A—H1AA | 109.7 | C2B—C1B—H1BA | 109.7 |
N1A—C1A—H1AB | 109.7 | N1B—C1B—H1BB | 109.7 |
C2A—C1A—H1AB | 109.7 | C2B—C1B—H1BB | 109.7 |
H1AA—C1A—H1AB | 108.2 | H1BA—C1B—H1BB | 108.2 |
O1A—C2A—C1A | 112.1 (3) | O1B—C2B—C1B | 111.5 (2) |
O1A—C2A—H2AB | 109.2 | O1B—C2B—H2BB | 109.3 |
C1A—C2A—H2AB | 109.2 | C1B—C2B—H2BB | 109.3 |
O1A—C2A—H2AC | 109.2 | O1B—C2B—H2BC | 109.3 |
C1A—C2A—H2AC | 109.2 | C1B—C2B—H2BC | 109.3 |
H2AB—C2A—H2AC | 107.9 | H2BB—C2B—H2BC | 108.0 |
O1A—C3A—C4A | 111.6 (2) | O1B—C3B—C4B | 111.9 (3) |
O1A—C3A—H3AB | 109.3 | O1B—C3B—H3BB | 109.2 |
C4A—C3A—H3AB | 109.3 | C4B—C3B—H3BB | 109.2 |
O1A—C3A—H3AC | 109.3 | O1B—C3B—H3BC | 109.2 |
C4A—C3A—H3AC | 109.3 | C4B—C3B—H3BC | 109.2 |
H3AB—C3A—H3AC | 108.0 | H3BB—C3B—H3BC | 107.9 |
N1A—C4A—C3A | 109.7 (2) | N1B—C4B—C3B | 109.6 (2) |
N1A—C4A—H4AB | 109.7 | N1B—C4B—H4BB | 109.7 |
C3A—C4A—H4AB | 109.7 | C3B—C4B—H4BB | 109.7 |
N1A—C4A—H4AC | 109.7 | N1B—C4B—H4BC | 109.7 |
C3A—C4A—H4AC | 109.7 | C3B—C4B—H4BC | 109.7 |
H4AB—C4A—H4AC | 108.2 | H4BB—C4B—H4BC | 108.2 |
N2A—C5A—N1A | 113.72 (17) | N1B—C5B—N2B | 113.76 (18) |
N2A—C5A—S1A | 124.82 (15) | N1B—C5B—S1B | 121.51 (16) |
N1A—C5A—S1A | 121.46 (15) | N2B—C5B—S1B | 124.73 (15) |
N3A—C6A—C7A | 116.28 (18) | N3B—C6B—C7B | 116.60 (18) |
N3A—C6A—C12A | 119.80 (19) | N3B—C6B—C12B | 120.09 (19) |
C7A—C6A—C12A | 123.90 (19) | C7B—C6B—C12B | 123.31 (19) |
N4A—C7A—C11A | 122.2 (2) | N4B—C7B—C11B | 122.5 (2) |
N4A—C7A—C6A | 115.72 (18) | N4B—C7B—C6B | 115.85 (18) |
C11A—C7A—C6A | 122.0 (2) | C11B—C7B—C6B | 121.7 (2) |
N4A—C8A—C9A | 124.0 (3) | N4B—C8B—C9B | 123.8 (2) |
N4A—C8A—H8AA | 118.0 | N4B—C8B—H8BA | 118.1 |
C9A—C8A—H8AA | 118.0 | C9B—C8B—H8BA | 118.1 |
C10A—C9A—C8A | 118.5 (3) | C10B—C9B—C8B | 118.8 (2) |
C10A—C9A—H9AA | 120.7 | C10B—C9B—H9BA | 120.6 |
C8A—C9A—H9AA | 120.7 | C8B—C9B—H9BA | 120.6 |
C9A—C10A—C11A | 119.0 (2) | C9B—C10B—C11B | 119.3 (2) |
C9A—C10A—H10A | 120.5 | C9B—C10B—H10B | 120.4 |
C11A—C10A—H10A | 120.5 | C11B—C10B—H10B | 120.4 |
C7A—C11A—C10A | 118.9 (2) | C10B—C11B—C7B | 118.3 (2) |
C7A—C11A—H11A | 120.6 | C10B—C11B—H11B | 120.9 |
C10A—C11A—H11A | 120.6 | C7B—C11B—H11B | 120.9 |
C6A—C12A—H12A | 109.5 | C6B—C12B—H12D | 109.5 |
C6A—C12A—H12B | 109.5 | C6B—C12B—H12E | 109.5 |
H12A—C12A—H12B | 109.5 | H12D—C12B—H12E | 109.5 |
C6A—C12A—H12C | 109.5 | C6B—C12B—H12F | 109.5 |
H12A—C12A—H12C | 109.5 | H12D—C12B—H12F | 109.5 |
H12B—C12A—H12C | 109.5 | H12E—C12B—H12F | 109.5 |
| | | |
C5A—N2A—N3A—C6A | 173.01 (18) | C5B—N2B—N3B—C6B | 176.05 (19) |
C5A—N1A—C1A—C2A | −127.6 (3) | C5B—N1B—C1B—C2B | −127.7 (3) |
C4A—N1A—C1A—C2A | 53.3 (3) | C4B—N1B—C1B—C2B | 53.3 (3) |
C3A—O1A—C2A—C1A | 59.4 (3) | C3B—O1B—C2B—C1B | 59.9 (3) |
N1A—C1A—C2A—O1A | −56.1 (3) | N1B—C1B—C2B—O1B | −56.5 (3) |
C2A—O1A—C3A—C4A | −59.8 (4) | C2B—O1B—C3B—C4B | −60.8 (4) |
C5A—N1A—C4A—C3A | 127.1 (3) | C5B—N1B—C4B—C3B | 127.4 (3) |
C1A—N1A—C4A—C3A | −53.8 (3) | C1B—N1B—C4B—C3B | −53.7 (3) |
O1A—C3A—C4A—N1A | 57.1 (3) | O1B—C3B—C4B—N1B | 57.8 (4) |
N3A—N2A—C5A—N1A | 176.28 (17) | C4B—N1B—C5B—N2B | −178.9 (2) |
N3A—N2A—C5A—S1A | −3.8 (2) | C1B—N1B—C5B—N2B | 2.3 (3) |
C4A—N1A—C5A—N2A | 175.2 (2) | C4B—N1B—C5B—S1B | 1.1 (3) |
C1A—N1A—C5A—N2A | −3.7 (3) | C1B—N1B—C5B—S1B | −177.71 (19) |
C4A—N1A—C5A—S1A | −4.7 (3) | N3B—N2B—C5B—N1B | 179.20 (18) |
C1A—N1A—C5A—S1A | 176.34 (19) | N3B—N2B—C5B—S1B | −0.8 (3) |
N2A—N3A—C6A—C7A | 178.18 (17) | N2B—N3B—C6B—C7B | 179.57 (17) |
N2A—N3A—C6A—C12A | −3.1 (3) | N2B—N3B—C6B—C12B | −0.9 (3) |
C8A—N4A—C7A—C11A | −1.0 (4) | C8B—N4B—C7B—C11B | 0.2 (3) |
C8A—N4A—C7A—C6A | 178.9 (2) | C8B—N4B—C7B—C6B | −179.5 (2) |
N3A—C6A—C7A—N4A | −3.3 (3) | N3B—C6B—C7B—N4B | 1.6 (3) |
C12A—C6A—C7A—N4A | 178.0 (2) | C12B—C6B—C7B—N4B | −177.9 (2) |
N3A—C6A—C7A—C11A | 176.54 (19) | N3B—C6B—C7B—C11B | −178.06 (19) |
C12A—C6A—C7A—C11A | −2.1 (3) | C12B—C6B—C7B—C11B | 2.4 (3) |
C7A—N4A—C8A—C9A | 0.6 (4) | C7B—N4B—C8B—C9B | −0.4 (4) |
N4A—C8A—C9A—C10A | 0.3 (4) | N4B—C8B—C9B—C10B | 0.2 (4) |
C8A—C9A—C10A—C11A | −0.7 (4) | C8B—C9B—C10B—C11B | 0.2 (4) |
N4A—C7A—C11A—C10A | 0.6 (3) | C9B—C10B—C11B—C7B | −0.4 (3) |
C6A—C7A—C11A—C10A | −179.3 (2) | N4B—C7B—C11B—C10B | 0.2 (3) |
C9A—C10A—C11A—C7A | 0.3 (4) | C6B—C7B—C11B—C10B | 179.85 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3A—H1N3···S1A | 0.90 (2) | 2.33 (2) | 2.837 (2) | 116 (2) |
N3A—H1N3···N4A | 0.90 (2) | 2.20 (3) | 2.626 (3) | 109 (2) |
N3B—H2N3···S1B | 0.86 (2) | 2.31 (2) | 2.835 (2) | 120 (2) |
N3B—H2N3···N4B | 0.86 (2) | 2.26 (2) | 2.639 (3) | 106 (2) |
C1A—H1AB···N2A | 0.97 | 2.27 | 2.703 (3) | 106 |
C2A—H2AC···S1Bi | 0.97 | 2.74 | 3.673 (3) | 161 |
C4A—H4AB···S1A | 0.97 | 2.56 | 3.081 (3) | 114 |
C1B—H1BB···N2B | 0.97 | 2.28 | 2.714 (3) | 106 |
C12A—H12A···N2A | 0.96 | 2.36 | 2.811 (3) | 108 |
C12B—H12D···N2B | 0.96 | 2.39 | 2.804 (3) | 105 |
C4B—H4BB···S1B | 0.97 | 2.56 | 3.077 (3) | 113 |
Symmetry code: (i) −x+1, y−1/2, −z+1/2. |