In the crystal structure of the title compound, C
14H
13N
3O
2S, intermolecular N—H
·O (H
O = 2.03 Å) and C—H
S (H
S = 2.77 Å) hydrogen bonds link molecules into a two-dimensional framework.
Supporting information
CCDC reference: 605067
Key indicators
- Single-crystal X-ray study
- T = 93 K
- Mean (N-C) = 0.002 Å
- Disorder in main residue
- R factor = 0.034
- wR factor = 0.095
- Data-to-parameter ratio = 14.2
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.96
PLAT301_ALERT_3_B Main Residue Disorder ......................... 41.00 Perc.
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.710 0.896
Tmin(prime) and Tmax expected: 0.820 0.896
RR(prime) = 0.866
Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.86
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.80 mm
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.67 Ratio
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 10
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 11.70 Deg.
C5B -C6 -C5A 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 12.20 Deg.
C8B -C7 -C8A 1.555 1.555 1.555
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
8 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
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
5 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.
N'-[(2-Methoxyphenyl)carbonothioyl]pyridine-2-carbohydrazide
top
Crystal data top
C14H13N3O2S | F(000) = 600 |
Mr = 287.33 | Dx = 1.412 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 14.608 (2) Å | Cell parameters from 5777 reflections |
b = 6.7090 (11) Å | θ = 3.0–28.3° |
c = 14.975 (3) Å | µ = 0.24 mm−1 |
β = 112.946 (3)° | T = 93 K |
V = 1351.5 (4) Å3 | Chunk, colorless |
Z = 4 | 0.80 × 0.55 × 0.45 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3221 independent reflections |
Radiation source: fine-focus sealed tube | 2639 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
φ and ω scans | θmax = 28.3°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | h = −19→18 |
Tmin = 0.710, Tmax = 0.896 | k = −8→8 |
10072 measured reflections | l = −19→17 |
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.095 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0487P)2 + 0.3326P] where P = (Fo2 + 2Fc2)/3 |
3221 reflections | (Δ/σ)max = 0.001 |
227 parameters | Δρmax = 0.26 e Å−3 |
29 restraints | Δρmin = −0.29 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 | Occ. (<1) |
S | 0.83866 (2) | 0.06430 (5) | 0.00872 (2) | 0.02585 (11) | |
O1 | 0.54300 (8) | 0.07166 (18) | 0.10792 (7) | 0.0415 (3) | |
N2 | 0.69304 (8) | 0.07700 (15) | 0.09786 (7) | 0.0214 (2) | |
H2A | 0.7579 | 0.0838 | 0.1297 | 0.026* | |
N3 | 0.65437 (7) | 0.06753 (15) | −0.00185 (7) | 0.0204 (2) | |
H3A | 0.5896 | 0.0644 | −0.0345 | 0.025* | |
N1A | 0.8024 (6) | 0.087 (2) | 0.2857 (8) | 0.0201 (10) | 0.444 (6) |
C1A | 0.8559 (5) | 0.0959 (18) | 0.3821 (7) | 0.0274 (10) | 0.444 (6) |
H1AA | 0.9260 | 0.1113 | 0.4044 | 0.033* | 0.444 (6) |
C2A | 0.8134 (5) | 0.0835 (13) | 0.4503 (6) | 0.0279 (10) | 0.444 (6) |
H2AA | 0.8542 | 0.0852 | 0.5175 | 0.033* | 0.444 (6) |
C3A | 0.7130 (6) | 0.0688 (13) | 0.4203 (5) | 0.0287 (10) | 0.444 (6) |
H3AA | 0.6832 | 0.0613 | 0.4663 | 0.034* | 0.444 (6) |
C4A | 0.6537 (5) | 0.0648 (17) | 0.3205 (6) | 0.0244 (8) | 0.444 (6) |
H4AA | 0.5833 | 0.0543 | 0.2966 | 0.029* | 0.444 (6) |
C5A | 0.7038 (6) | 0.077 (3) | 0.2594 (8) | 0.0174 (10) | 0.444 (6) |
N1B | 0.7793 (5) | 0.0908 (18) | 0.2886 (6) | 0.0201 (10) | 0.556 (6) |
C1B | 0.8272 (4) | 0.0856 (13) | 0.3849 (5) | 0.0274 (10) | 0.556 (6) |
H1BA | 0.8978 | 0.0861 | 0.4116 | 0.033* | 0.556 (6) |
C2B | 0.7773 (4) | 0.0793 (10) | 0.4480 (4) | 0.0279 (10) | 0.556 (6) |
H2BA | 0.8135 | 0.0762 | 0.5162 | 0.033* | 0.556 (6) |
C3B | 0.6755 (4) | 0.0777 (10) | 0.4100 (4) | 0.0287 (10) | 0.556 (6) |
H3BA | 0.6402 | 0.0730 | 0.4514 | 0.034* | 0.556 (6) |
C4B | 0.6244 (4) | 0.0831 (13) | 0.3094 (4) | 0.0244 (8) | 0.556 (6) |
H4BA | 0.5538 | 0.0857 | 0.2811 | 0.029* | 0.556 (6) |
C5B | 0.6789 (5) | 0.085 (2) | 0.2521 (6) | 0.0174 (10) | 0.556 (6) |
C6 | 0.63424 (10) | 0.07612 (19) | 0.14737 (9) | 0.0257 (3) | |
C7 | 0.71513 (9) | 0.06318 (18) | −0.04860 (8) | 0.0201 (2) | |
C8A | 0.6680 (10) | 0.0792 (13) | −0.1606 (8) | 0.0171 (12) | 0.481 (3) |
C9A | 0.6926 (5) | −0.0651 (8) | −0.2136 (4) | 0.0255 (8) | 0.481 (3) |
H9AA | 0.7384 | −0.1672 | −0.1808 | 0.031* | 0.481 (3) |
C10A | 0.6507 (5) | −0.0618 (7) | −0.3147 (4) | 0.0330 (9) | 0.481 (3) |
H10A | 0.6665 | −0.1623 | −0.3511 | 0.040* | 0.481 (3) |
C11A | 0.5858 (4) | 0.0902 (7) | −0.3611 (4) | 0.0309 (9) | 0.481 (3) |
H11A | 0.5569 | 0.0929 | −0.4300 | 0.037* | 0.481 (3) |
C12A | 0.5618 (5) | 0.2377 (7) | −0.3103 (5) | 0.0267 (9) | 0.481 (3) |
H12A | 0.5194 | 0.3437 | −0.3444 | 0.032* | 0.481 (3) |
C13A | 0.5994 (9) | 0.2334 (12) | −0.2082 (6) | 0.0176 (10) | 0.481 (3) |
O2A | 0.5802 (12) | 0.3726 (18) | −0.1527 (8) | 0.0246 (10) | 0.481 (3) |
C14A | 0.5174 (9) | 0.5362 (14) | −0.2031 (6) | 0.0454 (11) | 0.481 (3) |
H14A | 0.5111 | 0.6306 | −0.1559 | 0.068* | 0.481 (3) |
H14B | 0.4514 | 0.4854 | −0.2442 | 0.068* | 0.481 (3) |
H14C | 0.5468 | 0.6039 | −0.2436 | 0.068* | 0.481 (3) |
C8B | 0.6661 (9) | 0.0337 (11) | −0.1523 (7) | 0.0171 (12) | 0.519 (3) |
C9B | 0.6931 (5) | −0.1259 (7) | −0.1959 (4) | 0.0255 (8) | 0.519 (3) |
H9BA | 0.7372 | −0.2241 | −0.1563 | 0.031* | 0.519 (3) |
C10B | 0.6567 (4) | −0.1451 (7) | −0.2964 (3) | 0.0330 (9) | 0.519 (3) |
H10B | 0.6733 | −0.2585 | −0.3250 | 0.040* | 0.519 (3) |
C11B | 0.5966 (4) | 0.0011 (7) | −0.3537 (3) | 0.0309 (9) | 0.519 (3) |
H11B | 0.5732 | −0.0097 | −0.4222 | 0.037* | 0.519 (3) |
C12B | 0.5699 (5) | 0.1645 (7) | −0.3126 (4) | 0.0267 (9) | 0.519 (3) |
H12B | 0.5277 | 0.2647 | −0.3526 | 0.032* | 0.519 (3) |
C13B | 0.6053 (8) | 0.1801 (10) | −0.2124 (6) | 0.0176 (10) | 0.519 (3) |
O2B | 0.5831 (11) | 0.3365 (16) | −0.1655 (7) | 0.0246 (10) | 0.519 (3) |
C14B | 0.5219 (8) | 0.4937 (12) | −0.2239 (6) | 0.0454 (11) | 0.519 (3) |
H14D | 0.5158 | 0.6002 | −0.1817 | 0.068* | 0.519 (3) |
H14E | 0.4557 | 0.4410 | −0.2630 | 0.068* | 0.519 (3) |
H14F | 0.5523 | 0.5472 | −0.2668 | 0.068* | 0.519 (3) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S | 0.01668 (15) | 0.0318 (2) | 0.02236 (17) | −0.00139 (12) | 0.00025 (11) | 0.00169 (12) |
O1 | 0.0313 (5) | 0.0672 (8) | 0.0271 (5) | −0.0113 (5) | 0.0127 (4) | −0.0226 (5) |
N2 | 0.0242 (5) | 0.0230 (6) | 0.0112 (4) | 0.0006 (4) | 0.0008 (4) | −0.0005 (4) |
N3 | 0.0193 (5) | 0.0246 (6) | 0.0126 (4) | 0.0040 (4) | 0.0010 (4) | −0.0023 (4) |
N1A | 0.022 (3) | 0.0176 (7) | 0.0166 (7) | 0.004 (3) | 0.0029 (17) | −0.0006 (5) |
C1A | 0.032 (3) | 0.0196 (11) | 0.0192 (8) | −0.001 (2) | −0.002 (2) | 0.0000 (7) |
C2A | 0.043 (3) | 0.0189 (8) | 0.0151 (7) | −0.001 (3) | 0.004 (2) | 0.0009 (6) |
C3A | 0.049 (3) | 0.0187 (10) | 0.0219 (13) | −0.003 (3) | 0.018 (2) | −0.0018 (10) |
C4A | 0.031 (3) | 0.0194 (17) | 0.0219 (14) | −0.002 (2) | 0.0097 (19) | −0.0035 (12) |
C5A | 0.018 (3) | 0.0139 (11) | 0.0148 (12) | −0.001 (3) | 0.000 (2) | −0.0016 (10) |
N1B | 0.022 (3) | 0.0176 (7) | 0.0166 (7) | 0.004 (3) | 0.0029 (17) | −0.0006 (5) |
C1B | 0.032 (3) | 0.0196 (11) | 0.0192 (8) | −0.001 (2) | −0.002 (2) | 0.0000 (7) |
C2B | 0.043 (3) | 0.0189 (8) | 0.0151 (7) | −0.001 (3) | 0.004 (2) | 0.0009 (6) |
C3B | 0.049 (3) | 0.0187 (10) | 0.0219 (13) | −0.003 (3) | 0.018 (2) | −0.0018 (10) |
C4B | 0.031 (3) | 0.0194 (17) | 0.0219 (14) | −0.002 (2) | 0.0097 (19) | −0.0035 (12) |
C5B | 0.018 (3) | 0.0139 (11) | 0.0148 (12) | −0.001 (3) | 0.000 (2) | −0.0016 (10) |
C6 | 0.0351 (7) | 0.0228 (7) | 0.0177 (6) | −0.0043 (5) | 0.0086 (5) | −0.0061 (5) |
C7 | 0.0188 (5) | 0.0192 (6) | 0.0177 (5) | 0.0027 (4) | 0.0019 (4) | −0.0025 (4) |
C8A | 0.0161 (6) | 0.022 (3) | 0.0137 (14) | −0.004 (2) | 0.0067 (9) | 0.0002 (19) |
C9A | 0.0208 (6) | 0.032 (3) | 0.0243 (19) | −0.0009 (19) | 0.0099 (12) | −0.0047 (15) |
C10A | 0.0293 (10) | 0.050 (3) | 0.0250 (17) | −0.008 (2) | 0.0158 (12) | −0.0168 (18) |
C11A | 0.0207 (12) | 0.056 (3) | 0.0151 (9) | 0.001 (2) | 0.0058 (9) | −0.008 (2) |
C12A | 0.0205 (11) | 0.037 (3) | 0.0175 (7) | 0.003 (2) | 0.0021 (7) | 0.005 (2) |
C13A | 0.0164 (12) | 0.020 (4) | 0.0156 (8) | 0.005 (2) | 0.0056 (7) | −0.0031 (19) |
O2A | 0.0278 (9) | 0.023 (3) | 0.018 (2) | 0.010 (2) | 0.0023 (16) | −0.0011 (18) |
C14A | 0.0503 (13) | 0.034 (3) | 0.034 (3) | 0.025 (2) | −0.003 (2) | 0.002 (2) |
C8B | 0.0161 (6) | 0.022 (3) | 0.0137 (14) | −0.004 (2) | 0.0067 (9) | 0.0002 (19) |
C9B | 0.0208 (6) | 0.032 (3) | 0.0243 (19) | −0.0009 (19) | 0.0099 (12) | −0.0047 (15) |
C10B | 0.0293 (10) | 0.050 (3) | 0.0250 (17) | −0.008 (2) | 0.0158 (12) | −0.0168 (18) |
C11B | 0.0207 (12) | 0.056 (3) | 0.0151 (9) | 0.001 (2) | 0.0058 (9) | −0.008 (2) |
C12B | 0.0205 (11) | 0.037 (3) | 0.0175 (7) | 0.003 (2) | 0.0021 (7) | 0.005 (2) |
C13B | 0.0164 (12) | 0.020 (4) | 0.0156 (8) | 0.005 (2) | 0.0056 (7) | −0.0031 (19) |
O2B | 0.0278 (9) | 0.023 (3) | 0.018 (2) | 0.010 (2) | 0.0023 (16) | −0.0011 (18) |
C14B | 0.0503 (13) | 0.034 (3) | 0.034 (3) | 0.025 (2) | −0.003 (2) | 0.002 (2) |
Geometric parameters (Å, º) top
S—C7 | 1.6690 (12) | C8A—C9A | 1.385 (9) |
O1—C6 | 1.2299 (17) | C8A—C13A | 1.423 (9) |
N2—C6 | 1.3357 (17) | C9A—C10A | 1.395 (7) |
N2—N3 | 1.3767 (13) | C9A—H9AA | 0.9500 |
N2—H2A | 0.8800 | C10A—C11A | 1.381 (5) |
N3—C7 | 1.3279 (16) | C10A—H10A | 0.9500 |
N3—H3A | 0.8800 | C11A—C12A | 1.374 (5) |
N1A—C5A | 1.338 (8) | C11A—H11A | 0.9500 |
N1A—C1A | 1.348 (10) | C12A—C13A | 1.409 (8) |
C1A—C2A | 1.390 (8) | C12A—H12A | 0.9500 |
C1A—H1AA | 0.9500 | C13A—O2A | 1.351 (7) |
C2A—C3A | 1.359 (6) | O2A—C14A | 1.441 (9) |
C2A—H2AA | 0.9500 | C14A—H14A | 0.9800 |
C3A—C4A | 1.405 (8) | C14A—H14B | 0.9800 |
C3A—H3AA | 0.9500 | C14A—H14C | 0.9800 |
C4A—C5A | 1.379 (10) | C8B—C9B | 1.389 (8) |
C4A—H4AA | 0.9500 | C8B—C13B | 1.392 (8) |
C5A—C6 | 1.587 (10) | C9B—C10B | 1.393 (6) |
N1B—C1B | 1.335 (7) | C9B—H9BA | 0.9500 |
N1B—C5B | 1.351 (6) | C10B—C11B | 1.371 (5) |
C1B—C2B | 1.402 (6) | C10B—H10B | 0.9500 |
C1B—H1BA | 0.9500 | C11B—C12B | 1.386 (5) |
C2B—C3B | 1.369 (4) | C11B—H11B | 0.9500 |
C2B—H2BA | 0.9500 | C12B—C13B | 1.387 (8) |
C3B—C4B | 1.397 (6) | C12B—H12B | 0.9500 |
C3B—H3BA | 0.9500 | C13B—O2B | 1.371 (6) |
C4B—C5B | 1.380 (7) | O2B—C14B | 1.438 (9) |
C4B—H4BA | 0.9500 | C14B—H14D | 0.9800 |
C5B—C6 | 1.446 (8) | C14B—H14E | 0.9800 |
C7—C8B | 1.448 (10) | C14B—H14F | 0.9800 |
C7—C8A | 1.549 (11) | | |
| | | |
C6—N2—N3 | 121.41 (10) | N3—C7—S | 122.66 (9) |
C6—N2—H2A | 119.3 | C8B—C7—S | 122.4 (5) |
N3—N2—H2A | 119.3 | C8A—C7—S | 119.5 (5) |
C7—N3—N2 | 119.80 (10) | C9A—C8A—C13A | 120.7 (8) |
C7—N3—H3A | 120.1 | C9A—C8A—C7 | 117.8 (6) |
N2—N3—H3A | 120.1 | C13A—C8A—C7 | 121.4 (7) |
C5A—N1A—C1A | 115.2 (7) | C8A—C9A—C10A | 120.6 (6) |
N1A—C1A—C2A | 123.0 (6) | C8A—C9A—H9AA | 119.7 |
N1A—C1A—H1AA | 118.5 | C10A—C9A—H9AA | 119.7 |
C2A—C1A—H1AA | 118.5 | C11A—C10A—C9A | 118.8 (5) |
C3A—C2A—C1A | 119.7 (6) | C11A—C10A—H10A | 120.6 |
C3A—C2A—H2AA | 120.2 | C9A—C10A—H10A | 120.6 |
C1A—C2A—H2AA | 120.2 | C12A—C11A—C10A | 121.8 (5) |
C2A—C3A—C4A | 119.4 (6) | C12A—C11A—H11A | 119.1 |
C2A—C3A—H3AA | 120.3 | C10A—C11A—H11A | 119.1 |
C4A—C3A—H3AA | 120.3 | C11A—C12A—C13A | 120.7 (5) |
C5A—C4A—C3A | 116.0 (6) | C11A—C12A—H12A | 119.7 |
C5A—C4A—H4AA | 122.0 | C13A—C12A—H12A | 119.7 |
C3A—C4A—H4AA | 122.0 | O2A—C13A—C12A | 124.5 (7) |
N1A—C5A—C4A | 126.6 (8) | O2A—C13A—C8A | 118.0 (8) |
N1A—C5A—C6 | 118.9 (8) | C12A—C13A—C8A | 117.3 (6) |
C4A—C5A—C6 | 114.5 (6) | C13A—O2A—C14A | 116.5 (8) |
C1B—N1B—C5B | 117.7 (6) | C9B—C8B—C13B | 117.8 (7) |
N1B—C1B—C2B | 122.5 (4) | C9B—C8B—C7 | 119.8 (7) |
N1B—C1B—H1BA | 118.7 | C13B—C8B—C7 | 121.4 (6) |
C2B—C1B—H1BA | 118.7 | C8B—C9B—C10B | 121.3 (5) |
C3B—C2B—C1B | 119.1 (5) | C8B—C9B—H9BA | 119.3 |
C3B—C2B—H2BA | 120.5 | C10B—C9B—H9BA | 119.3 |
C1B—C2B—H2BA | 120.5 | C11B—C10B—C9B | 119.5 (4) |
C2B—C3B—C4B | 119.1 (4) | C11B—C10B—H10B | 120.3 |
C2B—C3B—H3BA | 120.5 | C9B—C10B—H10B | 120.3 |
C4B—C3B—H3BA | 120.5 | C10B—C11B—C12B | 120.7 (4) |
C5B—C4B—C3B | 118.3 (4) | C10B—C11B—H11B | 119.7 |
C5B—C4B—H4BA | 120.8 | C12B—C11B—H11B | 119.7 |
C3B—C4B—H4BA | 120.8 | C11B—C12B—C13B | 119.3 (4) |
N1B—C5B—C4B | 123.2 (6) | C11B—C12B—H12B | 120.4 |
N1B—C5B—C6 | 113.6 (6) | C13B—C12B—H12B | 120.4 |
C4B—C5B—C6 | 123.2 (5) | O2B—C13B—C12B | 123.3 (6) |
O1—C6—N2 | 122.99 (11) | O2B—C13B—C8B | 115.3 (7) |
O1—C6—C5B | 117.9 (3) | C12B—C13B—C8B | 121.4 (5) |
N2—C6—C5B | 119.1 (3) | C13B—O2B—C14B | 117.7 (7) |
O1—C6—C5A | 129.5 (4) | O2B—C14B—H14D | 109.5 |
N2—C6—C5A | 107.5 (3) | O2B—C14B—H14E | 109.5 |
C5B—C6—C5A | 11.7 (5) | H14D—C14B—H14E | 109.5 |
N3—C7—C8B | 114.5 (5) | O2B—C14B—H14F | 109.5 |
N3—C7—C8A | 117.6 (5) | H14D—C14B—H14F | 109.5 |
C8B—C7—C8A | 12.2 (7) | H14E—C14B—H14F | 109.5 |
| | | |
C6—N2—N3—C7 | −178.15 (11) | S—C7—C8A—C9A | 58.5 (10) |
C5A—N1A—C1A—C2A | 4 (2) | N3—C7—C8A—C13A | 50.8 (12) |
N1A—C1A—C2A—C3A | −2.4 (18) | C8B—C7—C8A—C13A | 129 (5) |
C1A—C2A—C3A—C4A | 0.5 (15) | S—C7—C8A—C13A | −123.2 (10) |
C2A—C3A—C4A—C5A | −0.2 (16) | C13A—C8A—C9A—C10A | 0.1 (15) |
C1A—N1A—C5A—C4A | −4 (2) | C7—C8A—C9A—C10A | 178.4 (7) |
C1A—N1A—C5A—C6 | 177.3 (12) | C8A—C9A—C10A—C11A | 1.3 (10) |
C3A—C4A—C5A—N1A | 2 (2) | C9A—C10A—C11A—C12A | 0.2 (9) |
C3A—C4A—C5A—C6 | −179.0 (9) | C10A—C11A—C12A—C13A | −3.0 (11) |
C5B—N1B—C1B—C2B | −1.7 (16) | C11A—C12A—C13A—O2A | 179.6 (12) |
N1B—C1B—C2B—C3B | 0.3 (13) | C11A—C12A—C13A—C8A | 4.3 (15) |
C1B—C2B—C3B—C4B | −0.3 (11) | C9A—C8A—C13A—O2A | −178.4 (12) |
C2B—C3B—C4B—C5B | 1.7 (12) | C7—C8A—C13A—O2A | 3.3 (18) |
C1B—N1B—C5B—C4B | 3.3 (18) | C9A—C8A—C13A—C12A | −2.8 (18) |
C1B—N1B—C5B—C6 | −175.7 (10) | C7—C8A—C13A—C12A | 178.9 (9) |
C3B—C4B—C5B—N1B | −3.3 (17) | C12A—C13A—O2A—C14A | −1 (2) |
C3B—C4B—C5B—C6 | 175.6 (9) | C8A—C13A—O2A—C14A | 174.7 (14) |
N3—N2—C6—O1 | −1.8 (2) | N3—C7—C8B—C9B | −122.9 (8) |
N3—N2—C6—C5B | 179.5 (6) | C8A—C7—C8B—C9B | 130 (5) |
N3—N2—C6—C5A | 177.1 (7) | S—C7—C8B—C9B | 50.2 (9) |
N1B—C5B—C6—O1 | −179.4 (8) | N3—C7—C8B—C13B | 68.9 (11) |
C4B—C5B—C6—O1 | 1.6 (14) | C8A—C7—C8B—C13B | −38 (3) |
N1B—C5B—C6—N2 | −0.6 (12) | S—C7—C8B—C13B | −118.1 (10) |
C4B—C5B—C6—N2 | −179.6 (8) | C13B—C8B—C9B—C10B | −3.2 (14) |
N1B—C5B—C6—C5A | 11 (5) | C7—C8B—C9B—C10B | −171.9 (6) |
C4B—C5B—C6—C5A | −168 (7) | C8B—C9B—C10B—C11B | 3.1 (9) |
N1A—C5A—C6—O1 | −178.4 (10) | C9B—C10B—C11B—C12B | −1.7 (8) |
C4A—C5A—C6—O1 | 2.3 (17) | C10B—C11B—C12B—C13B | 0.6 (10) |
N1A—C5A—C6—N2 | 2.8 (15) | C11B—C12B—C13B—O2B | 179.7 (10) |
C4A—C5A—C6—N2 | −176.4 (10) | C11B—C12B—C13B—C8B | −0.9 (15) |
N1A—C5A—C6—C5B | −167 (7) | C9B—C8B—C13B—O2B | −178.4 (11) |
C4A—C5A—C6—C5B | 14 (5) | C7—C8B—C13B—O2B | −9.9 (16) |
N2—N3—C7—C8B | 174.3 (3) | C9B—C8B—C13B—C12B | 2.1 (17) |
N2—N3—C7—C8A | −172.5 (4) | C7—C8B—C13B—C12B | 170.6 (9) |
N2—N3—C7—S | 1.22 (16) | C12B—C13B—O2B—C14B | −1 (2) |
N3—C7—C8A—C9A | −127.5 (8) | C8B—C13B—O2B—C14B | 179.0 (13) |
C8B—C7—C8A—C9A | −49 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···N1A | 0.88 | 2.17 | 2.639 (11) | 113 |
N3—H3A···O1i | 0.88 | 2.03 | 2.8524 (14) | 155 |
C2A—H2AA···O2Aii | 0.95 | 2.35 | 3.152 (13) | 141 |
C2B—H2BA···O2Aii | 0.95 | 2.45 | 3.268 (13) | 145 |
C12A—H12A···Siii | 0.95 | 2.77 | 3.584 (6) | 144 |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+3/2, y−1/2, −z+1/2; (iii) x−1/2, −y+1/2, z−1/2. |