The title compound, C18H26N2O4S, with two virtually identical molecules in the asymmetric unit, is found to adopt a distorted S conformation, with the carbonyl of the benzoyl group facing the opposite direction to the N-H amine bond, which lies in roughly the same direction as the C=S bond of the thiourea. The C-N bond of the thiourea on the acyl side of the molecule is much longer than the corresponding bond on the opposite side.
Supporting information
CCDC reference: 628417
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.004 Å
- R factor = 0.048
- wR factor = 0.115
- Data-to-parameter ratio = 14.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.93
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) ... 3.57 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for S1A - C2A .. 5.73 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for S1B - C2B .. 5.42 su
PLAT432_ALERT_2_C Short Inter X...Y Contact O1B .. C9B .. 2.99 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
C18 H26 N2 O4 S
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
7 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
5 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
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: X-SEED (Barbour, 2001).
N,
N-(Heptane-2,6-diyl)-
N'-(3,4,5-methoxybenzoyl)thiourea
top
Crystal data top
C18H26N2O4S | Z = 4 |
Mr = 366.47 | F(000) = 784 |
Triclinic, P1 | Dx = 1.279 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 12.427 (2) Å | Cell parameters from 18232 reflections |
b = 12.666 (2) Å | θ = 1.9–25.0° |
c = 13.894 (2) Å | µ = 0.19 mm−1 |
α = 96.486 (2)° | T = 173 K |
β = 91.758 (3)° | Block, colourless |
γ = 118.402 (2)° | 0.2 × 0.2 × 0.15 mm |
V = 1902.5 (5) Å3 | |
Data collection top
Bruker APEX CCD area-detector diffractometer | 5552 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.033 |
Graphite monochromator | θmax = 25.0°, θmin = 1.9° |
ω scans | h = −14→14 |
18232 measured reflections | k = −15→15 |
6672 independent reflections | l = −16→16 |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.115 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0491P)2 + 1.552P] where P = (Fo2 + 2Fc2)/3 |
6672 reflections | (Δ/σ)max < 0.001 |
461 parameters | Δρmax = 0.79 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
Special details top
Experimental. Selected assigned vibrational frequencies (IR, KBr pellets, cm-1) are 3167 (N–H
str), 1674 (C=O str), 1586, (N–H oop), 1421 (C2–N2 str), 1125 (N1–C2 str),
1216 (C1–N1 str) and 770 (C=S str). |
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 | 0.33229 (5) | 0.50582 (5) | 0.06041 (4) | 0.02321 (15) | |
O1A | 0.13216 (13) | 0.18752 (13) | 0.16127 (10) | 0.0202 (3) | |
N1A | 0.11363 (16) | 0.32526 (16) | 0.08053 (13) | 0.0181 (4) | |
H1A | 0.095 (2) | 0.380 (2) | 0.0871 (17) | 0.022* | |
C1A | 0.07963 (19) | 0.24548 (18) | 0.14817 (15) | 0.0169 (4) | |
S1B | −0.91223 (5) | −0.39797 (5) | 0.10656 (4) | 0.02402 (15) | |
O1B | −0.87791 (15) | −0.40905 (14) | 0.37952 (11) | 0.0269 (4) | |
N1B | −0.77448 (17) | −0.41027 (16) | 0.24952 (13) | 0.0193 (4) | |
H1B | −0.749 (2) | −0.449 (2) | 0.2110 (18) | 0.023* | |
C1B | −0.8189 (2) | −0.44933 (19) | 0.33513 (15) | 0.0190 (5) | |
O2A | −0.18138 (15) | 0.08622 (15) | 0.40937 (11) | 0.0278 (4) | |
N2A | 0.23427 (15) | 0.27498 (16) | −0.02222 (12) | 0.0178 (4) | |
C2A | 0.22399 (19) | 0.35953 (19) | 0.03595 (15) | 0.0171 (4) | |
O2B | −0.83657 (17) | −0.68989 (16) | 0.59109 (12) | 0.0348 (4) | |
N2B | −0.74695 (16) | −0.21672 (16) | 0.23992 (12) | 0.0183 (4) | |
C2B | −0.8073 (2) | −0.3338 (2) | 0.20349 (15) | 0.0194 (5) | |
O3A | −0.33308 (14) | 0.16367 (14) | 0.34987 (11) | 0.0253 (4) | |
C3A | −0.02784 (19) | 0.23227 (18) | 0.20147 (15) | 0.0177 (5) | |
O3B | −0.68254 (16) | −0.75442 (15) | 0.50842 (12) | 0.0300 (4) | |
C3B | −0.78538 (19) | −0.53597 (18) | 0.37404 (15) | 0.0188 (5) | |
O4A | −0.29145 (15) | 0.28974 (16) | 0.20069 (12) | 0.0299 (4) | |
C4A | −0.0496 (2) | 0.16896 (19) | 0.28080 (15) | 0.0196 (5) | |
H2A | 0.0047 | 0.1403 | 0.3002 | 0.024* | |
O4B | −0.59480 (15) | −0.68560 (14) | 0.34155 (11) | 0.0272 (4) | |
C4B | −0.8326 (2) | −0.57515 (19) | 0.46023 (16) | 0.0213 (5) | |
H12B | −0.8883 | −0.5520 | 0.4882 | 0.026* | |
C5A | −0.1506 (2) | 0.14808 (19) | 0.33106 (15) | 0.0206 (5) | |
C5B | −0.7983 (2) | −0.6480 (2) | 0.50539 (16) | 0.0230 (5) | |
C6A | −0.22996 (19) | 0.19032 (19) | 0.30268 (16) | 0.0202 (5) | |
C6B | −0.7176 (2) | −0.68294 (19) | 0.46292 (16) | 0.0214 (5) | |
C7A | −0.2072 (2) | 0.2537 (2) | 0.22316 (16) | 0.0206 (5) | |
C7B | −0.67293 (19) | −0.64604 (19) | 0.37530 (16) | 0.0197 (5) | |
C8A | −0.1065 (2) | 0.27454 (19) | 0.17212 (16) | 0.0200 (5) | |
H12A | −0.0915 | 0.3172 | 0.1177 | 0.024* | |
C8B | −0.70570 (19) | −0.57154 (19) | 0.33057 (16) | 0.0193 (5) | |
H2B | −0.6744 | −0.5451 | 0.2712 | 0.023* | |
C9A | −0.1048 (2) | 0.0383 (2) | 0.43941 (18) | 0.0330 (6) | |
H4A | −0.1017 | −0.0162 | 0.3849 | 0.049* | |
H5A | −0.1384 | −0.0068 | 0.4937 | 0.049* | |
H3A | −0.0217 | 0.1050 | 0.4602 | 0.049* | |
C9B | −0.9235 (3) | −0.6594 (3) | 0.6334 (2) | 0.0545 (9) | |
H11B | −0.8860 | −0.5711 | 0.6499 | 0.082* | |
H9B | −0.9481 | −0.6972 | 0.6924 | 0.082* | |
H10B | −0.9960 | −0.6891 | 0.5867 | 0.082* | |
C10A | −0.3246 (2) | 0.2640 (2) | 0.41513 (17) | 0.0297 (6) | |
H7A | −0.2547 | 0.2929 | 0.4642 | 0.045* | |
H6A | −0.4005 | 0.2380 | 0.4473 | 0.045* | |
H8A | −0.3130 | 0.3298 | 0.3784 | 0.045* | |
C10B | −0.5677 (3) | −0.6832 (3) | 0.56688 (19) | 0.0408 (7) | |
H6B | −0.5044 | −0.6352 | 0.5261 | 0.061* | |
H7B | −0.5441 | −0.7369 | 0.5962 | 0.061* | |
H8B | −0.5760 | −0.6286 | 0.6184 | 0.061* | |
C11A | −0.2668 (2) | 0.3641 (2) | 0.12534 (18) | 0.0331 (6) | |
H11A | −0.1866 | 0.4369 | 0.1418 | 0.050* | |
H9A | −0.3309 | 0.3878 | 0.1189 | 0.050* | |
H10A | −0.2662 | 0.3185 | 0.0637 | 0.050* | |
C11B | −0.5577 (2) | −0.6651 (2) | 0.24630 (17) | 0.0285 (5) | |
H4B | −0.6307 | −0.6994 | 0.1994 | 0.043* | |
H5B | −0.5078 | −0.7042 | 0.2292 | 0.043* | |
H3B | −0.5092 | −0.5777 | 0.2449 | 0.043* | |
C12A | 0.35399 (19) | 0.30603 (19) | −0.06167 (15) | 0.0184 (5) | |
H13A | 0.4176 | 0.3815 | −0.0202 | 0.022* | |
C12B | −0.7701 (2) | −0.1300 (2) | 0.19053 (17) | 0.0254 (5) | |
H13B | −0.8555 | −0.1764 | 0.1574 | 0.030* | |
C13A | 0.3885 (2) | 0.2071 (2) | −0.05115 (17) | 0.0230 (5) | |
H18A | 0.4056 | 0.2063 | 0.0188 | 0.028* | |
H17A | 0.4644 | 0.2254 | −0.0830 | 0.028* | |
C13B | −0.7661 (2) | −0.0291 (2) | 0.26421 (18) | 0.0278 (5) | |
H17B | −0.7696 | 0.0331 | 0.2290 | 0.033* | |
H18B | −0.8394 | −0.0632 | 0.3008 | 0.033* | |
C14A | 0.2855 (2) | 0.0815 (2) | −0.09684 (18) | 0.0315 (6) | |
H20A | 0.3093 | 0.0187 | −0.0875 | 0.038* | |
H19A | 0.2707 | 0.0797 | −0.1676 | 0.038* | |
C14B | −0.6516 (2) | 0.0308 (2) | 0.33548 (19) | 0.0307 (6) | |
H20B | −0.6537 | 0.0942 | 0.3828 | 0.037* | |
H19B | −0.5775 | 0.0695 | 0.3003 | 0.037* | |
C15A | 0.1677 (2) | 0.0558 (2) | −0.04665 (18) | 0.0314 (6) | |
H22A | 0.1000 | −0.0245 | −0.0760 | 0.038* | |
H21A | 0.1823 | 0.0529 | 0.0232 | 0.038* | |
C15B | −0.6474 (2) | −0.0662 (2) | 0.38841 (17) | 0.0274 (5) | |
H21B | −0.5733 | −0.0280 | 0.4357 | 0.033* | |
H22B | −0.7203 | −0.1015 | 0.4254 | 0.033* | |
C16A | 0.1292 (2) | 0.1523 (2) | −0.05638 (16) | 0.0250 (5) | |
H23A | 0.0640 | 0.1390 | −0.0114 | 0.030* | |
C16B | −0.6450 (2) | −0.1672 (2) | 0.31986 (15) | 0.0206 (5) | |
H23B | −0.6608 | −0.2345 | 0.3584 | 0.025* | |
C17A | 0.0736 (2) | 0.1423 (3) | −0.15749 (19) | 0.0381 (6) | |
H26A | 0.0518 | 0.2069 | −0.1596 | 0.057* | |
H24A | −0.0003 | 0.0632 | −0.1740 | 0.057* | |
H25A | 0.1334 | 0.1502 | −0.2044 | 0.057* | |
C17B | −0.5213 (2) | −0.1301 (2) | 0.27961 (18) | 0.0293 (5) | |
H24B | −0.5254 | −0.1992 | 0.2368 | 0.044* | |
H25B | −0.4575 | −0.1045 | 0.3335 | 0.044* | |
H26B | −0.5015 | −0.0627 | 0.2426 | 0.044* | |
C18A | 0.3553 (2) | 0.3353 (2) | −0.16559 (17) | 0.0285 (5) | |
H14A | 0.3042 | 0.2603 | −0.2104 | 0.043* | |
H15A | 0.4399 | 0.3725 | −0.1836 | 0.043* | |
H16A | 0.3227 | 0.3917 | −0.1693 | 0.043* | |
C18B | −0.6835 (3) | −0.0831 (3) | 0.11152 (19) | 0.0414 (7) | |
H16B | −0.6023 | −0.0204 | 0.1416 | 0.062* | |
H15B | −0.7163 | −0.0486 | 0.0667 | 0.062* | |
H14B | −0.6762 | −0.1502 | 0.0755 | 0.062* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1A | 0.0220 (3) | 0.0164 (3) | 0.0282 (3) | 0.0065 (2) | 0.0104 (2) | 0.0024 (2) |
O1A | 0.0217 (8) | 0.0223 (8) | 0.0195 (8) | 0.0125 (7) | 0.0048 (6) | 0.0041 (6) |
N1A | 0.0190 (9) | 0.0182 (10) | 0.0213 (10) | 0.0114 (8) | 0.0066 (8) | 0.0052 (8) |
C1A | 0.0171 (11) | 0.0137 (10) | 0.0151 (11) | 0.0046 (9) | 0.0002 (9) | −0.0028 (8) |
S1B | 0.0278 (3) | 0.0249 (3) | 0.0192 (3) | 0.0139 (3) | −0.0051 (2) | −0.0012 (2) |
O1B | 0.0361 (9) | 0.0337 (9) | 0.0244 (9) | 0.0263 (8) | 0.0099 (7) | 0.0086 (7) |
N1B | 0.0268 (10) | 0.0198 (10) | 0.0168 (9) | 0.0161 (9) | 0.0027 (8) | 0.0008 (8) |
C1B | 0.0212 (11) | 0.0181 (11) | 0.0180 (11) | 0.0101 (10) | 0.0007 (9) | 0.0009 (9) |
O2A | 0.0334 (9) | 0.0337 (9) | 0.0234 (9) | 0.0191 (8) | 0.0140 (7) | 0.0144 (7) |
N2A | 0.0152 (9) | 0.0184 (9) | 0.0177 (9) | 0.0063 (8) | 0.0045 (7) | 0.0022 (7) |
C2A | 0.0177 (11) | 0.0229 (11) | 0.0138 (10) | 0.0114 (9) | 0.0035 (8) | 0.0064 (9) |
O2B | 0.0491 (11) | 0.0468 (11) | 0.0328 (10) | 0.0374 (10) | 0.0263 (9) | 0.0247 (8) |
N2B | 0.0246 (10) | 0.0195 (10) | 0.0146 (9) | 0.0137 (8) | 0.0006 (8) | 0.0021 (7) |
C2B | 0.0246 (12) | 0.0242 (12) | 0.0153 (11) | 0.0160 (10) | 0.0057 (9) | 0.0042 (9) |
O3A | 0.0227 (8) | 0.0272 (9) | 0.0249 (9) | 0.0108 (7) | 0.0132 (7) | 0.0030 (7) |
C3A | 0.0193 (11) | 0.0147 (10) | 0.0153 (11) | 0.0061 (9) | 0.0022 (9) | −0.0021 (8) |
O3B | 0.0414 (10) | 0.0321 (9) | 0.0317 (9) | 0.0266 (8) | 0.0140 (8) | 0.0166 (8) |
C3B | 0.0209 (11) | 0.0148 (11) | 0.0193 (11) | 0.0083 (9) | −0.0011 (9) | −0.0006 (9) |
O4A | 0.0284 (9) | 0.0450 (10) | 0.0284 (9) | 0.0248 (8) | 0.0135 (7) | 0.0155 (8) |
C4A | 0.0204 (11) | 0.0199 (11) | 0.0174 (11) | 0.0095 (9) | 0.0016 (9) | −0.0007 (9) |
O4B | 0.0376 (10) | 0.0332 (9) | 0.0263 (9) | 0.0270 (8) | 0.0142 (7) | 0.0134 (7) |
C4B | 0.0231 (12) | 0.0206 (11) | 0.0244 (12) | 0.0135 (10) | 0.0058 (9) | 0.0041 (9) |
C5A | 0.0245 (12) | 0.0171 (11) | 0.0159 (11) | 0.0066 (10) | 0.0055 (9) | 0.0019 (9) |
C5B | 0.0267 (12) | 0.0212 (12) | 0.0237 (12) | 0.0122 (10) | 0.0081 (10) | 0.0091 (9) |
C6A | 0.0182 (11) | 0.0185 (11) | 0.0200 (11) | 0.0063 (9) | 0.0064 (9) | −0.0009 (9) |
C6B | 0.0240 (12) | 0.0169 (11) | 0.0255 (12) | 0.0105 (10) | 0.0046 (10) | 0.0072 (9) |
C7A | 0.0212 (11) | 0.0220 (12) | 0.0198 (11) | 0.0115 (10) | 0.0041 (9) | 0.0016 (9) |
C7B | 0.0199 (11) | 0.0170 (11) | 0.0238 (12) | 0.0102 (9) | 0.0031 (9) | 0.0028 (9) |
C8A | 0.0230 (12) | 0.0196 (11) | 0.0172 (11) | 0.0096 (10) | 0.0061 (9) | 0.0041 (9) |
C8B | 0.0216 (11) | 0.0175 (11) | 0.0185 (11) | 0.0093 (9) | 0.0028 (9) | 0.0027 (9) |
C9A | 0.0434 (15) | 0.0387 (15) | 0.0277 (13) | 0.0251 (13) | 0.0146 (12) | 0.0179 (11) |
C9B | 0.077 (2) | 0.074 (2) | 0.0564 (19) | 0.062 (2) | 0.0494 (18) | 0.0444 (17) |
C10A | 0.0356 (14) | 0.0380 (14) | 0.0201 (12) | 0.0215 (12) | 0.0108 (10) | 0.0016 (10) |
C10B | 0.0507 (17) | 0.0620 (19) | 0.0303 (14) | 0.0421 (16) | 0.0042 (13) | 0.0140 (13) |
C11A | 0.0380 (15) | 0.0503 (16) | 0.0275 (13) | 0.0311 (13) | 0.0149 (11) | 0.0185 (12) |
C11B | 0.0363 (14) | 0.0349 (14) | 0.0274 (13) | 0.0254 (12) | 0.0158 (11) | 0.0122 (11) |
C12A | 0.0153 (11) | 0.0191 (11) | 0.0186 (11) | 0.0066 (9) | 0.0050 (9) | 0.0015 (9) |
C12B | 0.0333 (13) | 0.0239 (12) | 0.0243 (12) | 0.0184 (11) | −0.0042 (10) | 0.0042 (10) |
C13A | 0.0219 (12) | 0.0284 (12) | 0.0231 (12) | 0.0146 (10) | 0.0083 (9) | 0.0076 (10) |
C13B | 0.0321 (13) | 0.0212 (12) | 0.0351 (14) | 0.0172 (11) | −0.0012 (11) | 0.0035 (10) |
C14A | 0.0362 (14) | 0.0303 (13) | 0.0293 (13) | 0.0168 (12) | 0.0079 (11) | 0.0053 (11) |
C14B | 0.0331 (14) | 0.0230 (12) | 0.0371 (14) | 0.0165 (11) | −0.0012 (11) | −0.0049 (11) |
C15A | 0.0419 (15) | 0.0197 (12) | 0.0232 (12) | 0.0073 (11) | 0.0069 (11) | 0.0019 (10) |
C15B | 0.0318 (13) | 0.0269 (13) | 0.0222 (12) | 0.0153 (11) | −0.0037 (10) | −0.0052 (10) |
C16A | 0.0163 (11) | 0.0263 (13) | 0.0222 (12) | 0.0030 (10) | 0.0059 (9) | −0.0021 (10) |
C16B | 0.0260 (12) | 0.0210 (11) | 0.0181 (11) | 0.0140 (10) | −0.0009 (9) | 0.0033 (9) |
C17A | 0.0334 (15) | 0.0435 (16) | 0.0366 (15) | 0.0211 (13) | −0.0086 (12) | −0.0062 (12) |
C17B | 0.0284 (13) | 0.0292 (13) | 0.0345 (14) | 0.0171 (11) | 0.0031 (11) | 0.0044 (11) |
C18A | 0.0285 (13) | 0.0351 (14) | 0.0247 (13) | 0.0155 (11) | 0.0120 (10) | 0.0115 (11) |
C18B | 0.066 (2) | 0.0428 (16) | 0.0294 (14) | 0.0346 (15) | 0.0104 (13) | 0.0180 (12) |
Geometric parameters (Å, º) top
S1A—C2A | 1.678 (2) | C10A—H7A | 0.9800 |
O1A—C1A | 1.215 (3) | C10A—H6A | 0.9800 |
N1A—C1A | 1.384 (3) | C10A—H8A | 0.9800 |
N1A—C2A | 1.414 (3) | C10B—H6B | 0.9800 |
N2A—C2A | 1.326 (3) | C10B—H7B | 0.9800 |
N1A—H1A | 0.83 (2) | C10B—H8B | 0.9800 |
C1A—C3A | 1.495 (3) | C11A—H11A | 0.9800 |
S1B—C2B | 1.677 (2) | C11A—H9A | 0.9800 |
O1B—C1B | 1.221 (3) | C11A—H10A | 0.9800 |
N1B—C1B | 1.370 (3) | C11B—H4B | 0.9800 |
N1B—C2B | 1.419 (3) | C11B—H5B | 0.9800 |
N1B—H1B | 0.85 (2) | C11B—H3B | 0.9800 |
C1B—C3B | 1.492 (3) | C12A—C13A | 1.524 (3) |
O2A—C5A | 1.370 (3) | C12A—C18A | 1.529 (3) |
O2A—C9A | 1.424 (3) | C12A—H13A | 1.0000 |
N2A—C16A | 1.487 (3) | C12B—C18B | 1.526 (4) |
N2A—C12A | 1.487 (3) | C12B—C13B | 1.525 (3) |
O2B—C5B | 1.365 (3) | C12B—H13B | 1.0000 |
O2B—C9B | 1.430 (3) | C13A—C14A | 1.535 (3) |
N2B—C2B | 1.329 (3) | C13A—H18A | 0.9900 |
N2B—C12B | 1.489 (3) | C13A—H17A | 0.9900 |
N2B—C16B | 1.494 (3) | C13B—C14B | 1.516 (3) |
O3A—C6A | 1.370 (3) | C13B—H17B | 0.9900 |
O3A—C10A | 1.434 (3) | C13B—H18B | 0.9900 |
C3A—C8A | 1.390 (3) | C14A—C15A | 1.548 (3) |
C3A—C4A | 1.394 (3) | C14A—H20A | 0.9900 |
O3B—C6B | 1.378 (3) | C14A—H19A | 0.9900 |
O3B—C10B | 1.431 (3) | C14B—C15B | 1.522 (3) |
C3B—C4B | 1.387 (3) | C14B—H20B | 0.9900 |
C3B—C8B | 1.396 (3) | C14B—H19B | 0.9900 |
O4A—C7A | 1.367 (3) | C15A—C16A | 1.527 (3) |
O4A—C11A | 1.430 (3) | C15A—H22A | 0.9900 |
C4A—C5A | 1.384 (3) | C15A—H21A | 0.9900 |
C4A—H2A | 0.9500 | C15B—C16B | 1.519 (3) |
O4B—C7B | 1.360 (3) | C15B—H21B | 0.9900 |
O4B—C11B | 1.426 (3) | C15B—H22B | 0.9900 |
C4B—C5B | 1.384 (3) | C16A—C17A | 1.511 (3) |
C4B—H12B | 0.9500 | C16A—H23A | 1.0000 |
C5A—C6A | 1.392 (3) | C16B—C17B | 1.523 (3) |
C5B—C6B | 1.396 (3) | C16B—H23B | 1.0000 |
C6A—C7A | 1.396 (3) | C17A—H26A | 0.9800 |
C6B—C7B | 1.390 (3) | C17A—H24A | 0.9800 |
C7A—C8A | 1.386 (3) | C17A—H25A | 0.9800 |
C7B—C8B | 1.387 (3) | C17B—H24B | 0.9800 |
C8A—H12A | 0.9500 | C17B—H25B | 0.9800 |
C8B—H2B | 0.9500 | C17B—H26B | 0.9800 |
C9A—H4A | 0.9800 | C18A—H14A | 0.9800 |
C9A—H5A | 0.9800 | C18A—H15A | 0.9800 |
C9A—H3A | 0.9800 | C18A—H16A | 0.9800 |
C9B—H11B | 0.9800 | C18B—H16B | 0.9800 |
C9B—H9B | 0.9800 | C18B—H15B | 0.9800 |
C9B—H10B | 0.9800 | C18B—H14B | 0.9800 |
| | | |
C1A—N1A—C2A | 121.35 (18) | O4A—C11A—H10A | 109.5 |
C1A—N1A—H1A | 118.3 (17) | H11A—C11A—H10A | 109.5 |
C2A—N1A—H1A | 112.4 (17) | H9A—C11A—H10A | 109.5 |
O1A—C1A—N1A | 121.76 (19) | O4B—C11B—H4B | 109.5 |
O1A—C1A—C3A | 122.30 (19) | O4B—C11B—H5B | 109.5 |
N1A—C1A—C3A | 115.91 (18) | H4B—C11B—H5B | 109.5 |
C1B—N1B—C2B | 121.57 (18) | O4B—C11B—H3B | 109.5 |
C1B—N1B—H1B | 121.6 (16) | H4B—C11B—H3B | 109.5 |
C2B—N1B—H1B | 113.3 (16) | H5B—C11B—H3B | 109.5 |
O1B—C1B—N1B | 120.58 (19) | N2A—C12A—C13A | 110.34 (17) |
O1B—C1B—C3B | 122.04 (19) | N2A—C12A—C18A | 111.94 (18) |
N1B—C1B—C3B | 117.27 (18) | C13A—C12A—C18A | 113.38 (18) |
C5A—O2A—C9A | 117.30 (17) | N2A—C12A—H13A | 106.9 |
C2A—N2A—C16A | 123.23 (17) | C13A—C12A—H13A | 106.9 |
C2A—N2A—C12A | 118.96 (17) | C18A—C12A—H13A | 106.9 |
C16A—N2A—C12A | 117.65 (16) | N2B—C12B—C18B | 110.91 (19) |
N2A—C2A—N1A | 118.14 (19) | N2B—C12B—C13B | 111.11 (18) |
N2A—C2A—S1A | 124.86 (16) | C18B—C12B—C13B | 113.3 (2) |
N1A—C2A—S1A | 116.99 (15) | N2B—C12B—H13B | 107.0 |
C5B—O2B—C9B | 115.96 (18) | C18B—C12B—H13B | 107.0 |
C2B—N2B—C12B | 118.66 (18) | C13B—C12B—H13B | 107.0 |
C2B—N2B—C16B | 122.15 (17) | C12A—C13A—C14A | 111.70 (19) |
C12B—N2B—C16B | 118.65 (17) | C12A—C13A—H18A | 109.3 |
N2B—C2B—N1B | 115.85 (19) | C14A—C13A—H18A | 109.3 |
N2B—C2B—S1B | 126.67 (16) | C12A—C13A—H17A | 109.3 |
N1B—C2B—S1B | 117.41 (16) | C14A—C13A—H17A | 109.3 |
C6A—O3A—C10A | 113.93 (17) | H18A—C13A—H17A | 107.9 |
C8A—C3A—C4A | 120.8 (2) | C14B—C13B—C12B | 112.76 (19) |
C8A—C3A—C1A | 122.93 (19) | C14B—C13B—H17B | 109.0 |
C4A—C3A—C1A | 116.18 (19) | C12B—C13B—H17B | 109.0 |
C6B—O3B—C10B | 111.62 (18) | C14B—C13B—H18B | 109.0 |
C4B—C3B—C8B | 120.8 (2) | C12B—C13B—H18B | 109.0 |
C4B—C3B—C1B | 116.17 (19) | H17B—C13B—H18B | 107.8 |
C8B—C3B—C1B | 122.90 (19) | C13A—C14A—C15A | 108.20 (19) |
C7A—O4A—C11A | 117.29 (17) | C13A—C14A—H20A | 110.1 |
C5A—C4A—C3A | 119.6 (2) | C15A—C14A—H20A | 110.1 |
C5A—C4A—H2A | 120.2 | C13A—C14A—H19A | 110.1 |
C3A—C4A—H2A | 120.2 | C15A—C14A—H19A | 110.1 |
C7B—O4B—C11B | 118.07 (17) | H20A—C14A—H19A | 108.4 |
C5B—C4B—C3B | 119.9 (2) | C13B—C14B—C15B | 108.25 (19) |
C5B—C4B—H12B | 120.0 | C13B—C14B—H20B | 110.0 |
C3B—C4B—H12B | 120.0 | C15B—C14B—H20B | 110.0 |
O2A—C5A—C4A | 124.5 (2) | C13B—C14B—H19B | 110.0 |
O2A—C5A—C6A | 115.27 (19) | C15B—C14B—H19B | 110.0 |
C4A—C5A—C6A | 120.2 (2) | H20B—C14B—H19B | 108.4 |
O2B—C5B—C4B | 125.2 (2) | C16A—C15A—C14A | 112.11 (19) |
O2B—C5B—C6B | 115.27 (19) | C16A—C15A—H22A | 109.2 |
C4B—C5B—C6B | 119.5 (2) | C14A—C15A—H22A | 109.2 |
O3A—C6A—C5A | 119.58 (19) | C16A—C15A—H21A | 109.2 |
O3A—C6A—C7A | 120.6 (2) | C14A—C15A—H21A | 109.2 |
C5A—C6A—C7A | 119.72 (19) | H22A—C15A—H21A | 107.9 |
O3B—C6B—C7B | 120.10 (19) | C16B—C15B—C14B | 112.85 (19) |
O3B—C6B—C5B | 119.53 (19) | C16B—C15B—H21B | 109.0 |
C7B—C6B—C5B | 120.4 (2) | C14B—C15B—H21B | 109.0 |
O4A—C7A—C8A | 124.5 (2) | C16B—C15B—H22B | 109.0 |
O4A—C7A—C6A | 115.02 (19) | C14B—C15B—H22B | 109.0 |
C8A—C7A—C6A | 120.5 (2) | H21B—C15B—H22B | 107.8 |
O4B—C7B—C8B | 124.98 (19) | N2A—C16A—C17A | 112.4 (2) |
O4B—C7B—C6B | 114.79 (18) | N2A—C16A—C15A | 109.94 (18) |
C8B—C7B—C6B | 120.20 (19) | C17A—C16A—C15A | 113.1 (2) |
C7A—C8A—C3A | 119.2 (2) | N2A—C16A—H23A | 107.0 |
C7A—C8A—H12A | 120.4 | C17A—C16A—H23A | 107.0 |
C3A—C8A—H12A | 120.4 | C15A—C16A—H23A | 107.0 |
C7B—C8B—C3B | 119.1 (2) | N2B—C16B—C15B | 110.50 (17) |
C7B—C8B—H2B | 120.5 | N2B—C16B—C17B | 111.37 (18) |
C3B—C8B—H2B | 120.5 | C15B—C16B—C17B | 113.45 (19) |
O2A—C9A—H4A | 109.5 | N2B—C16B—H23B | 107.1 |
O2A—C9A—H5A | 109.5 | C15B—C16B—H23B | 107.1 |
H4A—C9A—H5A | 109.5 | C17B—C16B—H23B | 107.1 |
O2A—C9A—H3A | 109.5 | C16A—C17A—H26A | 109.5 |
H4A—C9A—H3A | 109.5 | C16A—C17A—H24A | 109.5 |
H5A—C9A—H3A | 109.5 | H26A—C17A—H24A | 109.5 |
O2B—C9B—H11B | 109.5 | C16A—C17A—H25A | 109.5 |
O2B—C9B—H9B | 109.5 | H26A—C17A—H25A | 109.5 |
H11B—C9B—H9B | 109.5 | H24A—C17A—H25A | 109.5 |
O2B—C9B—H10B | 109.5 | C16B—C17B—H24B | 109.5 |
H11B—C9B—H10B | 109.5 | C16B—C17B—H25B | 109.5 |
H9B—C9B—H10B | 109.5 | H24B—C17B—H25B | 109.5 |
O3A—C10A—H7A | 109.5 | C16B—C17B—H26B | 109.5 |
O3A—C10A—H6A | 109.5 | H24B—C17B—H26B | 109.5 |
H7A—C10A—H6A | 109.5 | H25B—C17B—H26B | 109.5 |
O3A—C10A—H8A | 109.5 | C12A—C18A—H14A | 109.5 |
H7A—C10A—H8A | 109.5 | C12A—C18A—H15A | 109.5 |
H6A—C10A—H8A | 109.5 | H14A—C18A—H15A | 109.5 |
O3B—C10B—H6B | 109.5 | C12A—C18A—H16A | 109.5 |
O3B—C10B—H7B | 109.5 | H14A—C18A—H16A | 109.5 |
H6B—C10B—H7B | 109.5 | H15A—C18A—H16A | 109.5 |
O3B—C10B—H8B | 109.5 | C12B—C18B—H16B | 109.5 |
H6B—C10B—H8B | 109.5 | C12B—C18B—H15B | 109.5 |
H7B—C10B—H8B | 109.5 | H16B—C18B—H15B | 109.5 |
O4A—C11A—H11A | 109.5 | C12B—C18B—H14B | 109.5 |
O4A—C11A—H9A | 109.5 | H16B—C18B—H14B | 109.5 |
H11A—C11A—H9A | 109.5 | H15B—C18B—H14B | 109.5 |
| | | |
C2A—N1A—C1A—O1A | −11.4 (3) | C11A—O4A—C7A—C8A | −6.3 (3) |
C2A—N1A—C1A—C3A | 170.47 (18) | C11A—O4A—C7A—C6A | 174.6 (2) |
C2B—N1B—C1B—O1B | −7.7 (3) | O3A—C6A—C7A—O4A | 2.7 (3) |
C2B—N1B—C1B—C3B | 176.08 (19) | C5A—C6A—C7A—O4A | 179.21 (19) |
C16A—N2A—C2A—N1A | 10.9 (3) | O3A—C6A—C7A—C8A | −176.33 (19) |
C12A—N2A—C2A—N1A | −173.76 (18) | C5A—C6A—C7A—C8A | 0.2 (3) |
C16A—N2A—C2A—S1A | −168.51 (16) | C11B—O4B—C7B—C8B | −10.0 (3) |
C12A—N2A—C2A—S1A | 6.8 (3) | C11B—O4B—C7B—C6B | 171.9 (2) |
C1A—N1A—C2A—N2A | 65.5 (3) | O3B—C6B—C7B—O4B | −0.2 (3) |
C1A—N1A—C2A—S1A | −114.96 (19) | C5B—C6B—C7B—O4B | 179.8 (2) |
C12B—N2B—C2B—N1B | 175.52 (18) | O3B—C6B—C7B—C8B | −178.4 (2) |
C16B—N2B—C2B—N1B | 4.1 (3) | C5B—C6B—C7B—C8B | 1.7 (3) |
C12B—N2B—C2B—S1B | −1.5 (3) | O4A—C7A—C8A—C3A | −179.4 (2) |
C16B—N2B—C2B—S1B | −172.97 (16) | C6A—C7A—C8A—C3A | −0.4 (3) |
C1B—N1B—C2B—N2B | 79.8 (3) | C4A—C3A—C8A—C7A | 0.4 (3) |
C1B—N1B—C2B—S1B | −102.9 (2) | C1A—C3A—C8A—C7A | 177.09 (19) |
O1A—C1A—C3A—C8A | −164.3 (2) | O4B—C7B—C8B—C3B | −178.9 (2) |
N1A—C1A—C3A—C8A | 13.8 (3) | C6B—C7B—C8B—C3B | −1.0 (3) |
O1A—C1A—C3A—C4A | 12.5 (3) | C4B—C3B—C8B—C7B | −0.7 (3) |
N1A—C1A—C3A—C4A | −169.36 (18) | C1B—C3B—C8B—C7B | 175.65 (19) |
O1B—C1B—C3B—C4B | 4.5 (3) | C2A—N2A—C12A—C13A | 133.7 (2) |
N1B—C1B—C3B—C4B | −179.35 (19) | C16A—N2A—C12A—C13A | −50.7 (2) |
O1B—C1B—C3B—C8B | −171.9 (2) | C2A—N2A—C12A—C18A | −99.0 (2) |
N1B—C1B—C3B—C8B | 4.2 (3) | C16A—N2A—C12A—C18A | 76.6 (2) |
C8A—C3A—C4A—C5A | −0.1 (3) | C2B—N2B—C12B—C18B | −89.1 (2) |
C1A—C3A—C4A—C5A | −177.02 (19) | C16B—N2B—C12B—C18B | 82.7 (2) |
C8B—C3B—C4B—C5B | 1.6 (3) | C2B—N2B—C12B—C13B | 143.9 (2) |
C1B—C3B—C4B—C5B | −175.0 (2) | C16B—N2B—C12B—C13B | −44.3 (3) |
C9A—O2A—C5A—C4A | −1.3 (3) | N2A—C12A—C13A—C14A | 53.9 (2) |
C9A—O2A—C5A—C6A | 178.3 (2) | C18A—C12A—C13A—C14A | −72.6 (2) |
C3A—C4A—C5A—O2A | 179.44 (19) | N2B—C12B—C13B—C14B | 50.5 (3) |
C3A—C4A—C5A—C6A | −0.2 (3) | C18B—C12B—C13B—C14B | −75.1 (3) |
C9B—O2B—C5B—C4B | 3.2 (4) | C12A—C13A—C14A—C15A | −58.3 (2) |
C9B—O2B—C5B—C6B | −177.3 (2) | C12B—C13B—C14B—C15B | −58.4 (3) |
C3B—C4B—C5B—O2B | 178.6 (2) | C13A—C14A—C15A—C16A | 58.0 (3) |
C3B—C4B—C5B—C6B | −0.9 (3) | C13B—C14B—C15B—C16B | 59.3 (3) |
C10A—O3A—C6A—C5A | 105.3 (2) | C2A—N2A—C16A—C17A | 98.5 (2) |
C10A—O3A—C6A—C7A | −78.2 (3) | C12A—N2A—C16A—C17A | −76.9 (2) |
O2A—C5A—C6A—O3A | −3.0 (3) | C2A—N2A—C16A—C15A | −134.6 (2) |
C4A—C5A—C6A—O3A | 176.65 (19) | C12A—N2A—C16A—C15A | 50.1 (2) |
O2A—C5A—C6A—C7A | −179.50 (19) | C14A—C15A—C16A—N2A | −52.9 (3) |
C4A—C5A—C6A—C7A | 0.1 (3) | C14A—C15A—C16A—C17A | 73.7 (3) |
C10B—O3B—C6B—C7B | 84.3 (3) | C2B—N2B—C16B—C15B | −143.7 (2) |
C10B—O3B—C6B—C5B | −95.7 (2) | C12B—N2B—C16B—C15B | 44.8 (3) |
O2B—C5B—C6B—O3B | −0.2 (3) | C2B—N2B—C16B—C17B | 89.2 (2) |
C4B—C5B—C6B—O3B | 179.3 (2) | C12B—N2B—C16B—C17B | −82.3 (2) |
O2B—C5B—C6B—C7B | 179.8 (2) | C14B—C15B—C16B—N2B | −51.6 (3) |
C4B—C5B—C6B—C7B | −0.7 (3) | C14B—C15B—C16B—C17B | 74.2 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···S1Bi | 0.83 (2) | 2.84 (3) | 3.649 (2) | 167 (2) |
N1B—H1B···S1Aii | 0.85 (2) | 2.48 (3) | 3.274 (2) | 156 (2) |
Symmetry codes: (i) x+1, y+1, z; (ii) x−1, y−1, z. |