Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100009495/gg1010sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100009495/gg1010Isup2.hkl |
CCDC reference: 152621
The free amine of the title compound was synthesized and purified as reported previously (Jung et al., 1998) from (S)-phenylglycinol (converted into its hydrochloride in CH3OH saturated with HCl gas). After treatment of this CH3OH/HCl solution with ethyl acetate, an amorphous powder of the hydrochloride salt was obtained. The elemental analysis and IR spectrum showed that all terminal amine groups are protonated in the 1:1 hydrochloride salt. [Elemental analysis, calculated for C24H23N4O4S+·Cl−: C 57.77, H 4.65, N 11.23%; found: C 57.0 (5), H 4.4 (3), N 10.86 (8)%. IR spectrum (νmax, KBr, cm−1): 3200, 2800.] The amorphous salt was then treated in CH3OH/CH2Cl2 (7:1) co-solvent and slow evaporation produced single crystals of (I) suitablefor X-ray measurements. The elemental analysis and IR spectrum revealed (I) to have NH2, NH and NH3+ groups. [Elemental analysis, calculated for C24H23N4O4S+·Cl−·C24H22N4O4S: C 59.96, H 4.72, N 11.65; found: C 59.87 (5), H 4.45 (11), N 11.46 (13)%. IR spectrum (νmax, KBr, cm−1): 3330, 3200, 2800.]
The H atoms were treated using a riding model (C—H 0.93–0.98 Å and N—H 0.86–0.89 Å). The absolute structure was inferred not only from the absolute configuration of (S)-phenylglycinol used as starting material in the synthesis, but also determined by refining an enantiomorph-sensitive parameter to −0.07 (7) (Flack, 1983) using all 3715 Friedel pairs.
Data collection: CAD-4 EXPRESS (Enraf Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: WinGX (Farrugia, 1998); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Johnson et al., 1998); software used to prepare material for publication: WinGX.
C24H23N4O4S+·Cl−·C24H22N4O4S | Dx = 1.382 Mg m−3 |
Mr = 961.49 | Melting point: 489 K |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71069 Å |
a = 28.945 (3) Å | Cell parameters from 25 reflections |
b = 6.5473 (9) Å | θ = 11.4–14.2° |
c = 27.526 (2) Å | µ = 0.24 mm−1 |
β = 117.622 (7)° | T = 294 K |
V = 4621.9 (9) Å3 | Prism, pale brown |
Z = 4 | 0.43 × 0.40 × 0.33 mm |
F(000) = 2008 |
Enraf-Nonius CAD-4 diffractometer | 5916 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.030 |
Graphite monochromator | θmax = 25.2°, θmin = 2.1° |
ω–2θ scans | h = 0→34 |
Absorption correction: ψ scan (North et al., 1968) | k = −7→7 |
Tmin = 0.905, Tmax = 0.926 | l = −32→29 |
8420 measured reflections | 3 standard reflections every 300 min |
8252 independent reflections | intensity decay: 1% |
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)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.116 | w = 1/[σ2(Fo2) + (0.0486P)2 + 1.0617P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
8252 reflections | Δρmax = 0.28 e Å−3 |
605 parameters | Δρmin = −0.18 e Å−3 |
1 restraint | Absolute structure: (Flack, 1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.07 (7) |
C24H23N4O4S+·Cl−·C24H22N4O4S | V = 4621.9 (9) Å3 |
Mr = 961.49 | Z = 4 |
Monoclinic, C2 | Mo Kα radiation |
a = 28.945 (3) Å | µ = 0.24 mm−1 |
b = 6.5473 (9) Å | T = 294 K |
c = 27.526 (2) Å | 0.43 × 0.40 × 0.33 mm |
β = 117.622 (7)° |
Enraf-Nonius CAD-4 diffractometer | 5916 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.030 |
Tmin = 0.905, Tmax = 0.926 | 3 standard reflections every 300 min |
8420 measured reflections | intensity decay: 1% |
8252 independent reflections |
R[F2 > 2σ(F2)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.116 | Δρmax = 0.28 e Å−3 |
S = 1.02 | Δρmin = −0.18 e Å−3 |
8252 reflections | Absolute structure: (Flack, 1983) |
605 parameters | Absolute structure parameter: −0.07 (7) |
1 restraint |
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. Hydrogen bonding and contacts ############################# N1A H1A O7A 0.89 1.90 2.768 (4) 166.0 2_654 yes N1A H1B Cl1 0.89 2.22 3.110 (4) 174.0 2_665 yes N1A H1C O7B 0.89 2.36 3.086 (4) 138.9 2_655 yes N1A H1C N1B 0.89 2.51 3.008 (4) 115.9. yes N1B H1D O7B 0.86 2.23 2.980 (4) 144.9 2_655 yes N1B H1E Cl1 0.86 2.66 3.502 (4) 165.8 2_665 yes N3A H3A Cl1 0.86 2.32 3.106 (3) 152.5 1_554 yes N3B H3B Cl1 0.86 2.33 3.103 (3) 149.9. yes C18A H18A O8A 0.97 2.55 3.018 (4) 109.4 1_565 yes C19A H19B O8A 0.97 2.85 3.336 (5) 112.1 1_565 yes C27A H27A O5A 0.97 2.48 2.935 (4) 108.7 1_545 yes C28A H28A O5A 0.98 2.64 3.158 (5) 113.0 1_545 yes C18B H18C O8B 0.97 2.44 3.123 (5) 127.0 1_565 yes C19B H19D O8B 0.97 2.78 3.351 (5) 118.1 1_565 yes C27B H27C O5B 0.97 2.46 2.919 (4) 108.7 1_545 yes C28B H28B O5B 0.98 2.57 3.095 (5) 113.4 1_545 yes |
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. |
x | y | z | Uiso*/Ueq | ||
S1A | 0.71416 (3) | 0.77234 (14) | −0.58890 (4) | 0.0438 (2) | |
N1A | 0.50142 (12) | 0.8717 (5) | −0.28874 (13) | 0.0580 (9) | |
H1A | 0.4688 | 0.8287 | −0.3005 | 0.087* | |
H1B | 0.5033 | 1.0046 | −0.2813 | 0.087* | |
H1C | 0.5225 | 0.8036 | −0.2585 | 0.087* | |
N2A | 0.59478 (11) | 0.8413 (4) | −0.46512 (12) | 0.0472 (8) | |
N3A | 0.60953 (12) | 0.4745 (6) | −0.70211 (15) | 0.0738 (11) | |
H3A | 0.5770 | 0.4548 | −0.7237 | 0.089* | |
N4A | 0.68106 (11) | 0.6194 (4) | −0.64197 (12) | 0.0420 (7) | |
O5A | 0.71481 (10) | 0.9710 (4) | −0.60969 (10) | 0.0555 (7) | |
O6A | 0.76194 (9) | 0.6676 (4) | −0.55732 (10) | 0.0548 (7) | |
O7A | 0.60350 (10) | 0.8045 (4) | −0.67748 (10) | 0.0629 (7) | |
O8A | 0.57497 (12) | 0.5143 (4) | −0.45563 (11) | 0.0608 (8) | |
C11A | 0.51750 (14) | 0.8355 (6) | −0.33163 (14) | 0.0465 (9) | |
C12A | 0.49431 (15) | 0.6838 (6) | −0.36947 (15) | 0.0530 (10) | |
H12A | 0.4669 | 0.6088 | −0.3698 | 0.064* | |
C13A | 0.51225 (15) | 0.6434 (6) | −0.40746 (15) | 0.0538 (10) | |
H13A | 0.4975 | 0.5378 | −0.4326 | 0.065* | |
C14A | 0.55214 (13) | 0.7604 (6) | −0.40788 (14) | 0.0445 (9) | |
C15A | 0.57369 (15) | 0.9152 (6) | −0.37009 (15) | 0.0570 (11) | |
H15A | 0.6002 | 0.9951 | −0.3703 | 0.068* | |
C16A | 0.55648 (14) | 0.9529 (7) | −0.33199 (16) | 0.0578 (11) | |
H16A | 0.5712 | 1.0577 | −0.3066 | 0.069* | |
C17A | 0.57400 (15) | 0.6952 (6) | −0.44544 (15) | 0.0460 (9) | |
C18A | 0.58062 (16) | 1.0619 (5) | −0.47330 (16) | 0.0517 (10) | |
H18A | 0.6056 | 1.1433 | −0.4431 | 0.062* | |
H18B | 0.5461 | 1.0842 | −0.4767 | 0.062* | |
C19A | 0.58203 (16) | 1.1137 (6) | −0.52681 (16) | 0.0551 (10) | |
H19A | 0.5477 | 1.1014 | −0.5581 | 0.066* | |
H19B | 0.5952 | 1.2506 | −0.5258 | 0.066* | |
C20A | 0.61900 (14) | 0.9545 (6) | −0.52841 (14) | 0.0452 (9) | |
C21A | 0.62372 (13) | 0.7964 (6) | −0.49347 (13) | 0.0424 (8) | |
C22A | 0.65545 (15) | 0.6296 (6) | −0.48706 (15) | 0.0523 (10) | |
H22A | 0.6582 | 0.5237 | −0.4634 | 0.063* | |
C23A | 0.68294 (15) | 0.6244 (6) | −0.51676 (14) | 0.0511 (10) | |
H23A | 0.7046 | 0.5142 | −0.5131 | 0.061* | |
C24A | 0.67829 (13) | 0.7829 (6) | −0.55182 (13) | 0.0449 (8) | |
C25A | 0.64627 (14) | 0.9509 (6) | −0.55836 (14) | 0.0457 (9) | |
H25A | 0.6434 | 1.0570 | −0.5821 | 0.055* | |
C26A | 0.62749 (15) | 0.6473 (6) | −0.67577 (16) | 0.0502 (10) | |
C27A | 0.69450 (14) | 0.4040 (5) | −0.63966 (16) | 0.0526 (10) | |
H27A | 0.6964 | 0.3392 | −0.6071 | 0.063* | |
H27B | 0.7275 | 0.3857 | −0.6403 | 0.063* | |
C28A | 0.64877 (13) | 0.3192 (6) | −0.69205 (16) | 0.0518 (10) | |
H28A | 0.6373 | 0.1885 | −0.6840 | 0.062* | |
C29A | 0.66129 (13) | 0.2927 (7) | −0.73938 (15) | 0.0514 (9) | |
C30A | 0.68585 (16) | 0.1178 (7) | −0.74233 (18) | 0.0645 (12) | |
H30A | 0.6930 | 0.0163 | −0.7162 | 0.077* | |
C31A | 0.70015 (18) | 0.0884 (9) | −0.78298 (19) | 0.0805 (15) | |
H31A | 0.7170 | −0.0312 | −0.7840 | 0.097* | |
C32A | 0.68948 (18) | 0.2360 (11) | −0.8219 (2) | 0.0846 (18) | |
H32A | 0.6995 | 0.2187 | −0.8492 | 0.102* | |
C33A | 0.6643 (2) | 0.4070 (10) | −0.8202 (2) | 0.0899 (17) | |
H33A | 0.6564 | 0.5064 | −0.8471 | 0.108* | |
C34A | 0.64993 (16) | 0.4374 (8) | −0.77901 (19) | 0.0720 (13) | |
H34A | 0.6326 | 0.5562 | −0.7785 | 0.086* | |
S1B | 0.27780 (3) | 0.78296 (14) | 0.09839 (4) | 0.0432 (2) | |
N1B | 0.51914 (14) | 0.9075 (7) | −0.17240 (14) | 0.0867 (14) | |
H1D | 0.5437 | 0.8304 | −0.1712 | 0.104* | |
H1E | 0.5106 | 1.0163 | −0.1922 | 0.104* | |
N2B | 0.39633 (12) | 0.8567 (4) | −0.02600 (13) | 0.0492 (8) | |
N3B | 0.38135 (11) | 0.4796 (5) | 0.21321 (14) | 0.0633 (10) | |
H3B | 0.4135 | 0.4599 | 0.2363 | 0.076* | |
N4B | 0.31097 (11) | 0.6267 (4) | 0.15125 (11) | 0.0429 (7) | |
O5B | 0.27804 (10) | 0.9806 (4) | 0.12061 (10) | 0.0555 (7) | |
O6B | 0.22975 (9) | 0.6784 (4) | 0.06720 (10) | 0.0531 (7) | |
O7B | 0.38956 (9) | 0.8088 (4) | 0.19059 (10) | 0.0581 (7) | |
O8B | 0.40642 (12) | 0.5272 (4) | −0.04358 (12) | 0.0703 (9) | |
C11B | 0.49322 (16) | 0.8564 (7) | −0.14248 (16) | 0.0632 (12) | |
C12B | 0.50564 (17) | 0.6849 (7) | −0.11064 (17) | 0.0661 (12) | |
H12B | 0.5316 | 0.5982 | −0.1094 | 0.079* | |
C13B | 0.47998 (16) | 0.6379 (6) | −0.07999 (16) | 0.0589 (11) | |
H13B | 0.4880 | 0.5179 | −0.0596 | 0.071* | |
C14B | 0.44237 (14) | 0.7695 (7) | −0.07970 (14) | 0.0519 (9) | |
C15B | 0.42967 (16) | 0.9417 (7) | −0.11270 (16) | 0.0661 (12) | |
H15B | 0.4039 | 1.0295 | −0.1138 | 0.079* | |
C16B | 0.45433 (16) | 0.9856 (7) | −0.14383 (17) | 0.0706 (13) | |
H16B | 0.4450 | 1.1016 | −0.1658 | 0.085* | |
C17B | 0.41399 (16) | 0.7076 (6) | −0.04886 (15) | 0.0510 (10) | |
C18B | 0.4179 (2) | 1.0650 (6) | −0.0121 (2) | 0.0761 (15) | |
H18C | 0.4012 | 1.1549 | −0.0435 | 0.091* | |
H18D | 0.4552 | 1.0641 | −0.0001 | 0.091* | |
C19B | 0.40656 (16) | 1.1352 (6) | 0.03474 (16) | 0.0587 (11) | |
H19C | 0.4384 | 1.1436 | 0.0691 | 0.070* | |
H19D | 0.3895 | 1.2674 | 0.0267 | 0.070* | |
C20B | 0.37116 (14) | 0.9728 (6) | 0.03713 (14) | 0.0465 (9) | |
C21B | 0.36650 (13) | 0.8148 (6) | 0.00109 (14) | 0.0435 (9) | |
C22B | 0.33412 (14) | 0.6482 (6) | −0.00618 (15) | 0.0525 (10) | |
H22B | 0.3306 | 0.5445 | −0.0307 | 0.063* | |
C23B | 0.30709 (14) | 0.6415 (6) | 0.02440 (14) | 0.0473 (9) | |
H23B | 0.2851 | 0.5321 | 0.0202 | 0.057* | |
C24B | 0.31261 (13) | 0.7956 (6) | 0.06085 (13) | 0.0437 (8) | |
C25B | 0.34481 (14) | 0.9622 (6) | 0.06754 (14) | 0.0479 (9) | |
H25B | 0.3484 | 1.0652 | 0.0923 | 0.058* | |
C26B | 0.36438 (14) | 0.6526 (6) | 0.18626 (15) | 0.0456 (9) | |
C27B | 0.29620 (14) | 0.4132 (5) | 0.14870 (15) | 0.0493 (10) | |
H27C | 0.2938 | 0.3476 | 0.1160 | 0.059* | |
H27D | 0.2632 | 0.3987 | 0.1495 | 0.059* | |
C28B | 0.34152 (13) | 0.3249 (6) | 0.20097 (15) | 0.0500 (9) | |
H28B | 0.3531 | 0.1957 | 0.1922 | 0.060* | |
C29B | 0.32817 (12) | 0.2918 (6) | 0.24743 (14) | 0.0470 (9) | |
C30B | 0.30355 (15) | 0.1123 (7) | 0.24913 (17) | 0.0582 (11) | |
H30B | 0.2967 | 0.0131 | 0.2225 | 0.070* | |
C31B | 0.28897 (16) | 0.0780 (8) | 0.28944 (19) | 0.0738 (14) | |
H31B | 0.2722 | −0.0429 | 0.2898 | 0.089* | |
C32B | 0.29920 (18) | 0.2221 (10) | 0.3290 (2) | 0.0799 (17) | |
H32B | 0.2891 | 0.2002 | 0.3561 | 0.096* | |
C33B | 0.32398 (19) | 0.3970 (10) | 0.32865 (19) | 0.0887 (17) | |
H33B | 0.3313 | 0.4941 | 0.3559 | 0.106* | |
C34B | 0.33852 (17) | 0.4323 (8) | 0.28775 (18) | 0.0715 (13) | |
H34B | 0.3555 | 0.5531 | 0.2879 | 0.086* | |
Cl1 | 0.49530 (4) | 0.32892 (18) | 0.25666 (6) | 0.0866 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1A | 0.0473 (5) | 0.0366 (5) | 0.0482 (5) | −0.0009 (5) | 0.0227 (5) | −0.0008 (5) |
N1A | 0.0577 (19) | 0.063 (2) | 0.056 (2) | −0.0062 (18) | 0.0286 (17) | −0.0038 (17) |
N2A | 0.0629 (19) | 0.0328 (18) | 0.0512 (18) | 0.0052 (15) | 0.0310 (17) | −0.0030 (15) |
N3A | 0.0343 (18) | 0.074 (3) | 0.107 (3) | −0.0089 (18) | 0.0274 (19) | −0.041 (2) |
N4A | 0.0411 (17) | 0.0321 (16) | 0.0473 (17) | 0.0049 (14) | 0.0158 (15) | −0.0016 (14) |
O5A | 0.0707 (18) | 0.0358 (15) | 0.0685 (17) | −0.0073 (14) | 0.0395 (15) | 0.0005 (14) |
O6A | 0.0452 (15) | 0.0601 (18) | 0.0530 (16) | 0.0063 (13) | 0.0176 (13) | −0.0020 (14) |
O7A | 0.0533 (15) | 0.0611 (19) | 0.0680 (17) | 0.0178 (15) | 0.0229 (14) | −0.0045 (16) |
O8A | 0.093 (2) | 0.0349 (16) | 0.0690 (18) | 0.0053 (15) | 0.0503 (17) | 0.0006 (13) |
C11A | 0.049 (2) | 0.056 (3) | 0.0362 (19) | −0.0024 (19) | 0.0209 (18) | −0.0061 (18) |
C12A | 0.055 (2) | 0.054 (2) | 0.055 (2) | −0.006 (2) | 0.029 (2) | 0.003 (2) |
C13A | 0.069 (3) | 0.047 (2) | 0.046 (2) | −0.013 (2) | 0.027 (2) | −0.0095 (19) |
C14A | 0.045 (2) | 0.043 (2) | 0.0415 (19) | 0.0015 (19) | 0.0165 (17) | 0.0005 (19) |
C15A | 0.055 (2) | 0.070 (3) | 0.058 (2) | −0.019 (2) | 0.036 (2) | −0.020 (2) |
C16A | 0.053 (2) | 0.065 (3) | 0.058 (2) | −0.019 (2) | 0.028 (2) | −0.024 (2) |
C17A | 0.056 (2) | 0.039 (2) | 0.040 (2) | 0.0066 (18) | 0.0199 (19) | −0.0011 (17) |
C18A | 0.070 (3) | 0.034 (2) | 0.062 (3) | 0.0095 (19) | 0.039 (2) | −0.0024 (19) |
C19A | 0.067 (3) | 0.038 (2) | 0.065 (3) | 0.008 (2) | 0.034 (2) | 0.005 (2) |
C20A | 0.053 (2) | 0.031 (2) | 0.047 (2) | 0.0047 (18) | 0.019 (2) | −0.0040 (18) |
C21A | 0.052 (2) | 0.037 (2) | 0.0390 (18) | 0.0016 (19) | 0.0218 (17) | −0.0021 (18) |
C22A | 0.074 (3) | 0.038 (2) | 0.050 (2) | 0.011 (2) | 0.032 (2) | 0.0093 (19) |
C23A | 0.064 (2) | 0.041 (2) | 0.052 (2) | 0.016 (2) | 0.030 (2) | 0.0095 (19) |
C24A | 0.051 (2) | 0.038 (2) | 0.047 (2) | 0.0033 (19) | 0.0247 (18) | −0.002 (2) |
C25A | 0.058 (2) | 0.034 (2) | 0.048 (2) | 0.0018 (19) | 0.026 (2) | −0.0014 (18) |
C26A | 0.047 (2) | 0.052 (3) | 0.059 (2) | −0.003 (2) | 0.030 (2) | −0.010 (2) |
C27A | 0.059 (2) | 0.034 (2) | 0.067 (3) | 0.0002 (19) | 0.031 (2) | −0.0039 (19) |
C28A | 0.051 (2) | 0.037 (2) | 0.078 (3) | −0.0102 (18) | 0.039 (2) | −0.014 (2) |
C29A | 0.0381 (19) | 0.053 (2) | 0.058 (2) | −0.003 (2) | 0.0178 (19) | −0.006 (2) |
C30A | 0.063 (3) | 0.066 (3) | 0.070 (3) | 0.010 (2) | 0.036 (2) | 0.000 (2) |
C31A | 0.069 (3) | 0.112 (4) | 0.069 (3) | 0.012 (3) | 0.039 (3) | −0.009 (3) |
C32A | 0.054 (3) | 0.141 (6) | 0.058 (3) | −0.008 (3) | 0.026 (3) | −0.007 (4) |
C33A | 0.077 (4) | 0.117 (5) | 0.057 (3) | −0.002 (4) | 0.016 (3) | 0.026 (3) |
C34A | 0.063 (3) | 0.066 (3) | 0.078 (3) | 0.007 (2) | 0.025 (3) | 0.005 (3) |
S1B | 0.0468 (5) | 0.0343 (5) | 0.0445 (5) | 0.0011 (5) | 0.0177 (4) | 0.0025 (5) |
N1B | 0.084 (3) | 0.125 (4) | 0.071 (3) | 0.020 (3) | 0.053 (2) | 0.022 (3) |
N2B | 0.062 (2) | 0.0360 (18) | 0.055 (2) | 0.0013 (16) | 0.0310 (17) | 0.0075 (15) |
N3B | 0.0324 (17) | 0.063 (2) | 0.081 (2) | 0.0048 (17) | 0.0144 (17) | 0.035 (2) |
N4B | 0.0423 (17) | 0.0334 (16) | 0.0422 (17) | −0.0049 (14) | 0.0105 (15) | 0.0050 (14) |
O5B | 0.0735 (19) | 0.0356 (15) | 0.0615 (17) | 0.0057 (14) | 0.0348 (15) | 0.0008 (13) |
O6B | 0.0411 (14) | 0.0568 (17) | 0.0513 (15) | −0.0009 (13) | 0.0128 (12) | 0.0011 (13) |
O7B | 0.0578 (16) | 0.0541 (18) | 0.0541 (15) | −0.0188 (15) | 0.0190 (13) | 0.0000 (14) |
O8B | 0.102 (2) | 0.0446 (19) | 0.082 (2) | −0.0106 (17) | 0.057 (2) | −0.0044 (16) |
C11B | 0.055 (2) | 0.084 (3) | 0.048 (3) | 0.001 (2) | 0.021 (2) | 0.008 (2) |
C12B | 0.065 (3) | 0.069 (3) | 0.062 (3) | 0.015 (2) | 0.027 (2) | 0.002 (2) |
C13B | 0.070 (3) | 0.052 (3) | 0.056 (3) | 0.005 (2) | 0.030 (2) | 0.005 (2) |
C14B | 0.051 (2) | 0.054 (2) | 0.046 (2) | 0.004 (2) | 0.0184 (19) | 0.007 (2) |
C15B | 0.056 (3) | 0.077 (3) | 0.068 (3) | 0.020 (2) | 0.031 (2) | 0.029 (3) |
C16B | 0.071 (3) | 0.081 (3) | 0.066 (3) | 0.016 (3) | 0.038 (3) | 0.035 (3) |
C17B | 0.061 (3) | 0.046 (3) | 0.042 (2) | −0.003 (2) | 0.020 (2) | 0.0028 (18) |
C18B | 0.105 (4) | 0.035 (2) | 0.119 (4) | −0.012 (2) | 0.077 (4) | −0.003 (3) |
C19B | 0.070 (3) | 0.035 (2) | 0.072 (3) | −0.006 (2) | 0.034 (2) | 0.003 (2) |
C20B | 0.051 (2) | 0.035 (2) | 0.046 (2) | 0.0003 (18) | 0.017 (2) | 0.0069 (18) |
C21B | 0.046 (2) | 0.038 (2) | 0.0409 (19) | 0.0042 (18) | 0.0163 (18) | 0.0059 (18) |
C22B | 0.059 (2) | 0.046 (2) | 0.048 (2) | −0.006 (2) | 0.021 (2) | −0.008 (2) |
C23B | 0.052 (2) | 0.040 (2) | 0.046 (2) | −0.0108 (18) | 0.0190 (19) | −0.0045 (18) |
C24B | 0.0451 (19) | 0.041 (2) | 0.0355 (17) | −0.0016 (19) | 0.0105 (16) | 0.0044 (19) |
C25B | 0.059 (2) | 0.036 (2) | 0.042 (2) | 0.0016 (19) | 0.018 (2) | 0.0000 (18) |
C26B | 0.047 (2) | 0.044 (2) | 0.047 (2) | −0.0023 (19) | 0.0227 (19) | 0.0028 (19) |
C27B | 0.048 (2) | 0.037 (2) | 0.055 (2) | −0.0031 (18) | 0.018 (2) | 0.0038 (18) |
C28B | 0.043 (2) | 0.041 (2) | 0.063 (2) | 0.0015 (18) | 0.0222 (19) | 0.011 (2) |
C29B | 0.0359 (18) | 0.046 (2) | 0.053 (2) | 0.0040 (19) | 0.0156 (18) | 0.007 (2) |
C30B | 0.057 (3) | 0.057 (3) | 0.063 (3) | −0.011 (2) | 0.030 (2) | −0.005 (2) |
C31B | 0.063 (3) | 0.092 (4) | 0.072 (3) | −0.017 (3) | 0.036 (3) | 0.005 (3) |
C32B | 0.056 (3) | 0.129 (5) | 0.059 (3) | 0.001 (3) | 0.030 (3) | 0.005 (3) |
C33B | 0.081 (4) | 0.123 (5) | 0.053 (3) | 0.001 (4) | 0.024 (3) | −0.025 (3) |
C34B | 0.070 (3) | 0.069 (3) | 0.072 (3) | −0.015 (3) | 0.030 (3) | −0.015 (3) |
Cl1 | 0.0445 (6) | 0.0603 (8) | 0.1507 (12) | 0.0005 (6) | 0.0415 (7) | −0.0034 (8) |
S1A—O6A | 1.423 (3) | S1B—O6B | 1.426 (3) |
S1A—O5A | 1.424 (3) | S1B—O5B | 1.430 (3) |
S1A—N4A | 1.660 (3) | S1B—N4B | 1.670 (3) |
S1A—C24A | 1.763 (3) | S1B—C24B | 1.748 (3) |
N1A—C11A | 1.475 (4) | N1B—C11B | 1.388 (5) |
N1A—H1A | 0.8900 | N1B—H1D | 0.8600 |
N1A—H1B | 0.8900 | N1B—H1E | 0.8600 |
N1A—H1C | 0.8900 | N2B—C17B | 1.382 (5) |
N2A—C17A | 1.368 (5) | N2B—C21B | 1.405 (4) |
N2A—C21A | 1.416 (4) | N2B—C18B | 1.475 (5) |
N2A—C18A | 1.490 (4) | N3B—C26B | 1.318 (5) |
N3A—C26A | 1.314 (5) | N3B—C28B | 1.452 (4) |
N3A—C28A | 1.452 (5) | N3B—H3B | 0.8600 |
N3A—H3A | 0.8600 | N4B—C26B | 1.402 (4) |
N4A—C26A | 1.402 (4) | N4B—C27B | 1.454 (4) |
N4A—C27A | 1.457 (4) | O7B—C26B | 1.229 (4) |
O7A—C26A | 1.230 (4) | O8B—C17B | 1.222 (4) |
O8A—C17A | 1.221 (4) | C11B—C12B | 1.366 (6) |
C11A—C12A | 1.368 (5) | C11B—C16B | 1.394 (6) |
C11A—C16A | 1.369 (5) | C12B—C13B | 1.392 (6) |
C12A—C13A | 1.392 (5) | C12B—H12B | 0.9300 |
C12A—H12A | 0.9300 | C13B—C14B | 1.391 (5) |
C13A—C14A | 1.390 (5) | C13B—H13B | 0.9300 |
C13A—H13A | 0.9300 | C14B—C15B | 1.387 (5) |
C14A—C15A | 1.377 (5) | C14B—C17B | 1.485 (5) |
C14A—C17A | 1.503 (5) | C15B—C16B | 1.376 (5) |
C15A—C16A | 1.376 (5) | C15B—H15B | 0.9300 |
C15A—H15A | 0.9300 | C16B—H16B | 0.9300 |
C16A—H16A | 0.9300 | C18B—C19B | 1.540 (6) |
C18A—C19A | 1.530 (5) | C18B—H18C | 0.9700 |
C18A—H18A | 0.9700 | C18B—H18D | 0.9700 |
C18A—H18B | 0.9700 | C19B—C20B | 1.499 (5) |
C19A—C20A | 1.509 (5) | C19B—H19C | 0.9700 |
C19A—H19A | 0.9700 | C19B—H19D | 0.9700 |
C19A—H19B | 0.9700 | C20B—C25B | 1.371 (5) |
C20A—C21A | 1.376 (5) | C20B—C21B | 1.396 (5) |
C20A—C25A | 1.381 (5) | C21B—C22B | 1.391 (5) |
C21A—C22A | 1.385 (5) | C22B—C23B | 1.391 (5) |
C22A—C23A | 1.380 (5) | C22B—H22B | 0.9300 |
C22A—H22A | 0.9300 | C23B—C24B | 1.379 (5) |
C23A—C24A | 1.380 (5) | C23B—H23B | 0.9300 |
C23A—H23A | 0.9300 | C24B—C25B | 1.391 (5) |
C24A—C25A | 1.396 (5) | C25B—H25B | 0.9300 |
C25A—H25A | 0.9300 | C27B—C28B | 1.541 (5) |
C27A—C28A | 1.539 (5) | C27B—H27C | 0.9700 |
C27A—H27A | 0.9700 | C27B—H27D | 0.9700 |
C27A—H27B | 0.9700 | C28B—C29B | 1.513 (5) |
C28A—C29A | 1.515 (5) | C28B—H28B | 0.9800 |
C28A—H28A | 0.9800 | C29B—C34B | 1.364 (6) |
C29A—C34A | 1.365 (6) | C29B—C30B | 1.386 (6) |
C29A—C30A | 1.370 (6) | C30B—C31B | 1.376 (5) |
C30A—C31A | 1.375 (6) | C30B—H30B | 0.9300 |
C30A—H30A | 0.9300 | C31B—C32B | 1.365 (7) |
C31A—C32A | 1.367 (7) | C31B—H31B | 0.9300 |
C31A—H31A | 0.9300 | C32B—C33B | 1.353 (7) |
C32A—C33A | 1.348 (7) | C32B—H32B | 0.9300 |
C32A—H32A | 0.9300 | C33B—C34B | 1.392 (6) |
C33A—C34A | 1.392 (7) | C33B—H33B | 0.9300 |
C33A—H33A | 0.9300 | C34B—H34B | 0.9300 |
C34A—H34A | 0.9300 | ||
O6A—S1A—O5A | 119.69 (17) | C33A—C34A—H34A | 120.0 |
O6A—S1A—N4A | 104.36 (15) | O6B—S1B—O5B | 120.15 (16) |
O5A—S1A—N4A | 107.86 (16) | O6B—S1B—N4B | 103.69 (15) |
O6A—S1A—C24A | 109.38 (16) | O5B—S1B—N4B | 107.15 (15) |
O5A—S1A—C24A | 108.54 (17) | O6B—S1B—C24B | 109.59 (16) |
N4A—S1A—C24A | 106.17 (16) | O5B—S1B—C24B | 108.67 (17) |
C11A—N1A—H1A | 109.5 | N4B—S1B—C24B | 106.74 (16) |
C11A—N1A—H1B | 109.5 | C11B—N1B—H1D | 120.0 |
H1A—N1A—H1B | 109.5 | C11B—N1B—H1E | 120.0 |
C11A—N1A—H1C | 109.5 | H1D—N1B—H1E | 120.0 |
H1A—N1A—H1C | 109.5 | C17B—N2B—C21B | 123.5 (3) |
H1B—N1A—H1C | 109.5 | C17B—N2B—C18B | 124.8 (3) |
C17A—N2A—C21A | 123.7 (3) | C21B—N2B—C18B | 109.5 (3) |
C17A—N2A—C18A | 126.7 (3) | C26B—N3B—C28B | 114.9 (3) |
C21A—N2A—C18A | 108.0 (3) | C26B—N3B—H3B | 122.6 |
C26A—N3A—C28A | 115.1 (3) | C28B—N3B—H3B | 122.6 |
C26A—N3A—H3A | 122.5 | C26B—N4B—C27B | 110.8 (3) |
C28A—N3A—H3A | 122.5 | C26B—N4B—S1B | 122.0 (2) |
C26A—N4A—C27A | 110.2 (3) | C27B—N4B—S1B | 120.6 (2) |
C26A—N4A—S1A | 121.0 (2) | C12B—C11B—N1B | 121.7 (4) |
C27A—N4A—S1A | 120.8 (2) | C12B—C11B—C16B | 119.0 (4) |
C12A—C11A—C16A | 121.1 (3) | N1B—C11B—C16B | 119.3 (4) |
C12A—C11A—N1A | 120.0 (3) | C11B—C12B—C13B | 121.0 (4) |
C16A—C11A—N1A | 118.8 (3) | C11B—C12B—H12B | 119.5 |
C11A—C12A—C13A | 119.2 (4) | C13B—C12B—H12B | 119.5 |
C11A—C12A—H12A | 120.4 | C14B—C13B—C12B | 120.3 (4) |
C13A—C12A—H12A | 120.4 | C14B—C13B—H13B | 119.8 |
C14A—C13A—C12A | 120.1 (4) | C12B—C13B—H13B | 119.8 |
C14A—C13A—H13A | 119.9 | C15B—C14B—C13B | 118.1 (4) |
C12A—C13A—H13A | 119.9 | C15B—C14B—C17B | 123.2 (4) |
C15A—C14A—C13A | 119.1 (3) | C13B—C14B—C17B | 118.4 (4) |
C15A—C14A—C17A | 122.8 (3) | C16B—C15B—C14B | 121.4 (4) |
C13A—C14A—C17A | 117.7 (3) | C16B—C15B—H15B | 119.3 |
C16A—C15A—C14A | 120.7 (4) | C14B—C15B—H15B | 119.3 |
C16A—C15A—H15A | 119.7 | C15B—C16B—C11B | 120.1 (4) |
C14A—C15A—H15A | 119.7 | C15B—C16B—H16B | 119.9 |
C11A—C16A—C15A | 119.7 (4) | C11B—C16B—H16B | 119.9 |
C11A—C16A—H16A | 120.2 | O8B—C17B—N2B | 120.3 (4) |
C15A—C16A—H16A | 120.2 | O8B—C17B—C14B | 120.6 (4) |
O8A—C17A—N2A | 121.8 (3) | N2B—C17B—C14B | 119.1 (3) |
O8A—C17A—C14A | 119.7 (4) | N2B—C18B—C19B | 105.3 (3) |
N2A—C17A—C14A | 118.5 (3) | N2B—C18B—H18C | 110.7 |
N2A—C18A—C19A | 103.4 (3) | C19B—C18B—H18C | 110.7 |
N2A—C18A—H18A | 111.1 | N2B—C18B—H18D | 110.7 |
C19A—C18A—H18A | 111.1 | C19B—C18B—H18D | 110.7 |
N2A—C18A—H18B | 111.1 | H18C—C18B—H18D | 108.8 |
C19A—C18A—H18B | 111.1 | C20B—C19B—C18B | 103.9 (3) |
H18A—C18A—H18B | 109.0 | C20B—C19B—H19C | 111.0 |
C20A—C19A—C18A | 102.2 (3) | C18B—C19B—H19C | 111.0 |
C20A—C19A—H19A | 111.3 | C20B—C19B—H19D | 111.0 |
C18A—C19A—H19A | 111.3 | C18B—C19B—H19D | 111.0 |
C20A—C19A—H19B | 111.3 | H19C—C19B—H19D | 109.0 |
C18A—C19A—H19B | 111.3 | C25B—C20B—C21B | 119.9 (3) |
H19A—C19A—H19B | 109.2 | C25B—C20B—C19B | 130.4 (4) |
C21A—C20A—C25A | 120.4 (3) | C21B—C20B—C19B | 109.7 (3) |
C21A—C20A—C19A | 109.9 (3) | C22B—C21B—C20B | 121.3 (3) |
C25A—C20A—C19A | 129.7 (3) | C22B—C21B—N2B | 128.0 (3) |
C20A—C21A—C22A | 121.8 (3) | C20B—C21B—N2B | 110.6 (3) |
C20A—C21A—N2A | 109.7 (3) | C23B—C22B—C21B | 117.9 (3) |
C22A—C21A—N2A | 128.4 (3) | C23B—C22B—H22B | 121.0 |
C23A—C22A—C21A | 118.3 (3) | C21B—C22B—H22B | 121.0 |
C23A—C22A—H22A | 120.8 | C24B—C23B—C22B | 120.7 (3) |
C21A—C22A—H22A | 120.8 | C24B—C23B—H23B | 119.7 |
C22A—C23A—C24A | 120.0 (4) | C22B—C23B—H23B | 119.7 |
C22A—C23A—H23A | 120.0 | C23B—C24B—C25B | 121.0 (3) |
C24A—C23A—H23A | 120.0 | C23B—C24B—S1B | 119.4 (3) |
C23A—C24A—C25A | 121.8 (3) | C25B—C24B—S1B | 119.6 (3) |
C23A—C24A—S1A | 118.9 (3) | C20B—C25B—C24B | 119.2 (3) |
C25A—C24A—S1A | 119.4 (3) | C20B—C25B—H25B | 120.4 |
C20A—C25A—C24A | 117.7 (3) | C24B—C25B—H25B | 120.4 |
C20A—C25A—H25A | 121.1 | O7B—C26B—N3B | 127.7 (4) |
C24A—C25A—H25A | 121.1 | O7B—C26B—N4B | 125.6 (3) |
O7A—C26A—N3A | 128.9 (4) | N3B—C26B—N4B | 106.7 (3) |
O7A—C26A—N4A | 124.4 (4) | N4B—C27B—C28B | 102.2 (3) |
N3A—C26A—N4A | 106.7 (3) | N4B—C27B—H27C | 111.3 |
N4A—C27A—C28A | 102.2 (3) | C28B—C27B—H27C | 111.3 |
N4A—C27A—H27A | 111.3 | N4B—C27B—H27D | 111.3 |
C28A—C27A—H27A | 111.3 | C28B—C27B—H27D | 111.3 |
N4A—C27A—H27B | 111.3 | H27C—C27B—H27D | 109.2 |
C28A—C27A—H27B | 111.3 | N3B—C28B—C29B | 113.0 (3) |
H27A—C27A—H27B | 109.2 | N3B—C28B—C27B | 101.3 (3) |
N3A—C28A—C29A | 113.2 (3) | C29B—C28B—C27B | 113.7 (3) |
N3A—C28A—C27A | 100.5 (3) | N3B—C28B—H28B | 109.5 |
C29A—C28A—C27A | 113.7 (3) | C29B—C28B—H28B | 109.5 |
N3A—C28A—H28A | 109.7 | C27B—C28B—H28B | 109.5 |
C29A—C28A—H28A | 109.7 | C34B—C29B—C30B | 117.8 (4) |
C27A—C28A—H28A | 109.7 | C34B—C29B—C28B | 123.0 (4) |
C34A—C29A—C30A | 118.2 (4) | C30B—C29B—C28B | 119.1 (4) |
C34A—C29A—C28A | 122.9 (4) | C31B—C30B—C29B | 121.4 (4) |
C30A—C29A—C28A | 118.9 (4) | C31B—C30B—H30B | 119.3 |
C29A—C30A—C31A | 121.7 (5) | C29B—C30B—H30B | 119.3 |
C29A—C30A—H30A | 119.1 | C32B—C31B—C30B | 119.7 (5) |
C31A—C30A—H30A | 119.1 | C32B—C31B—H31B | 120.2 |
C32A—C31A—C30A | 119.6 (5) | C30B—C31B—H31B | 120.2 |
C32A—C31A—H31A | 120.2 | C33B—C32B—C31B | 120.0 (5) |
C30A—C31A—H31A | 120.2 | C33B—C32B—H32B | 120.0 |
C33A—C32A—C31A | 119.4 (5) | C31B—C32B—H32B | 120.0 |
C33A—C32A—H32A | 120.3 | C32B—C33B—C34B | 120.4 (5) |
C31A—C32A—H32A | 120.3 | C32B—C33B—H33B | 119.8 |
C32A—C33A—C34A | 121.1 (5) | C34B—C33B—H33B | 119.8 |
C32A—C33A—H33A | 119.5 | C29B—C34B—C33B | 120.7 (5) |
C34A—C33A—H33A | 119.5 | C29B—C34B—H34B | 119.6 |
C29A—C34A—C33A | 120.0 (5) | C33B—C34B—H34B | 119.6 |
C29A—C34A—H34A | 120.0 | ||
O6A—S1A—N4A—C26A | 165.3 (3) | O6B—S1B—N4B—C26B | 167.1 (3) |
O5A—S1A—N4A—C26A | −66.4 (3) | O5B—S1B—N4B—C26B | −64.8 (3) |
C24A—S1A—N4A—C26A | 49.8 (3) | C24B—S1B—N4B—C26B | 51.4 (3) |
O6A—S1A—N4A—C27A | 19.5 (3) | O6B—S1B—N4B—C27B | 18.2 (3) |
O5A—S1A—N4A—C27A | 147.8 (3) | O5B—S1B—N4B—C27B | 146.2 (3) |
C24A—S1A—N4A—C27A | −96.1 (3) | C24B—S1B—N4B—C27B | −97.5 (3) |
C16A—C11A—C12A—C13A | 2.7 (6) | N1B—C11B—C12B—C13B | 178.7 (4) |
N1A—C11A—C12A—C13A | −176.0 (3) | C16B—C11B—C12B—C13B | 0.2 (7) |
C11A—C12A—C13A—C14A | −2.0 (6) | C11B—C12B—C13B—C14B | −2.4 (6) |
C12A—C13A—C14A—C15A | 0.4 (6) | C12B—C13B—C14B—C15B | 3.1 (6) |
C12A—C13A—C14A—C17A | 173.3 (3) | C12B—C13B—C14B—C17B | 176.7 (4) |
C13A—C14A—C15A—C16A | 0.6 (6) | C13B—C14B—C15B—C16B | −1.8 (6) |
C17A—C14A—C15A—C16A | −171.9 (4) | C17B—C14B—C15B—C16B | −175.1 (4) |
C12A—C11A—C16A—C15A | −1.7 (6) | C14B—C15B—C16B—C11B | −0.3 (7) |
N1A—C11A—C16A—C15A | 177.0 (4) | C12B—C11B—C16B—C15B | 1.1 (7) |
C14A—C15A—C16A—C11A | 0.0 (6) | N1B—C11B—C16B—C15B | −177.4 (4) |
C21A—N2A—C17A—O8A | −7.0 (6) | C21B—N2B—C17B—O8B | −4.1 (6) |
C18A—N2A—C17A—O8A | 156.6 (4) | C18B—N2B—C17B—O8B | 157.0 (4) |
C18A—N2A—C17A—C14A | −26.8 (5) | C18B—N2B—C17B—C14B | −22.9 (6) |
C21A—N2A—C17A—C14A | 169.7 (3) | C21B—N2B—C17B—C14B | 176.1 (3) |
C15A—C14A—C17A—O8A | 141.2 (4) | C15B—C14B—C17B—O8B | 143.3 (4) |
C13A—C14A—C17A—O8A | −31.4 (5) | C13B—C14B—C17B—O8B | −30.0 (6) |
C15A—C14A—C17A—N2A | −35.6 (5) | C15B—C14B—C17B—N2B | −36.9 (6) |
C13A—C14A—C17A—N2A | 151.9 (3) | C13B—C14B—C17B—N2B | 149.8 (4) |
C17A—N2A—C18A—C19A | −141.4 (4) | C17B—N2B—C18B—C19B | −153.4 (3) |
C21A—N2A—C18A—C19A | 24.3 (4) | C21B—N2B—C18B—C19B | 9.8 (4) |
N2A—C18A—C19A—C20A | −24.8 (4) | N2B—C18B—C19B—C20B | −9.3 (4) |
C18A—C19A—C20A—C21A | 18.2 (4) | C18B—C19B—C20B—C21B | 5.9 (4) |
C18A—C19A—C20A—C25A | −161.6 (4) | C18B—C19B—C20B—C25B | −173.7 (4) |
C25A—C20A—C21A—C22A | −0.1 (6) | C25B—C20B—C21B—C22B | 2.2 (5) |
C19A—C20A—C21A—C22A | −180.0 (3) | C19B—C20B—C21B—C22B | −177.5 (3) |
C25A—C20A—C21A—N2A | 176.3 (3) | C25B—C20B—C21B—N2B | 179.7 (3) |
C19A—C20A—C21A—N2A | −3.5 (4) | C19B—C20B—C21B—N2B | 0.1 (4) |
C17A—N2A—C21A—C20A | 152.7 (3) | C17B—N2B—C21B—C22B | −25.6 (5) |
C18A—N2A—C21A—C20A | −13.5 (4) | C17B—N2B—C21B—C20B | 157.1 (3) |
C17A—N2A—C21A—C22A | −31.1 (6) | C18B—N2B—C21B—C20B | −6.4 (4) |
C18A—N2A—C21A—C22A | 162.7 (4) | C18B—N2B—C21B—C22B | 170.9 (4) |
C20A—C21A—C22A—C23A | 0.2 (6) | C20B—C21B—C22B—C23B | −1.2 (5) |
N2A—C21A—C22A—C23A | −175.6 (3) | N2B—C21B—C22B—C23B | −178.2 (3) |
C21A—C22A—C23A—C24A | −0.1 (6) | C21B—C22B—C23B—C24B | −0.2 (5) |
C22A—C23A—C24A—C25A | 0.1 (6) | C22B—C23B—C24B—C25B | 0.7 (5) |
C22A—C23A—C24A—S1A | 179.7 (3) | C22B—C23B—C24B—S1B | 179.7 (3) |
O6A—S1A—C24A—C23A | −31.9 (4) | O6B—S1B—C24B—C23B | −30.6 (3) |
O5A—S1A—C24A—C23A | −164.1 (3) | O5B—S1B—C24B—C23B | −163.7 (3) |
N4A—S1A—C24A—C23A | 80.2 (3) | N4B—S1B—C24B—C23B | 81.0 (3) |
O6A—S1A—C24A—C25A | 147.8 (3) | O6B—S1B—C24B—C25B | 148.4 (3) |
O5A—S1A—C24A—C25A | 15.6 (3) | O5B—S1B—C24B—C25B | 15.3 (3) |
N4A—S1A—C24A—C25A | −100.2 (3) | N4B—S1B—C24B—C25B | −99.9 (3) |
C21A—C20A—C25A—C24A | 0.0 (5) | C21B—C20B—C25B—C24B | −1.7 (5) |
C19A—C20A—C25A—C24A | 179.8 (4) | C19B—C20B—C25B—C24B | 177.9 (4) |
C23A—C24A—C25A—C20A | 0.0 (5) | C23B—C24B—C25B—C20B | 0.3 (5) |
S1A—C24A—C25A—C20A | −179.6 (3) | S1B—C24B—C25B—C20B | −178.7 (3) |
C28A—N3A—C26A—O7A | 178.3 (4) | C28B—N3B—C26B—O7B | 177.2 (4) |
C28A—N3A—C26A—N4A | −4.0 (5) | C28B—N3B—C26B—N4B | −2.2 (5) |
C27A—N4A—C26A—O7A | 166.0 (4) | C27B—N4B—C26B—O7B | 168.9 (4) |
S1A—N4A—C26A—O7A | 16.9 (5) | S1B—N4B—C26B—O7B | 17.3 (5) |
C27A—N4A—C26A—N3A | −11.9 (4) | C27B—N4B—C26B—N3B | −11.7 (4) |
S1A—N4A—C26A—N3A | −161.0 (3) | S1B—N4B—C26B—N3B | −163.3 (3) |
C26A—N4A—C27A—C28A | 21.3 (4) | C26B—N4B—C27B—C28B | 19.5 (4) |
S1A—N4A—C27A—C28A | 170.5 (2) | S1B—N4B—C27B—C28B | 171.5 (2) |
C26A—N3A—C28A—C29A | −105.0 (4) | C26B—N3B—C28B—C29B | −108.2 (4) |
C26A—N3A—C28A—C27A | 16.7 (5) | C26B—N3B—C28B—C27B | 13.8 (4) |
N4A—C27A—C28A—N3A | −21.4 (4) | N4B—C27B—C28B—N3B | −18.8 (4) |
N4A—C27A—C28A—C29A | 99.9 (4) | N4B—C27B—C28B—C29B | 102.7 (4) |
N3A—C28A—C29A—C34A | 19.1 (5) | N3B—C28B—C29B—C34B | 20.4 (5) |
C27A—C28A—C29A—C34A | −94.8 (4) | C27B—C28B—C29B—C34B | −94.3 (4) |
N3A—C28A—C29A—C30A | −162.0 (3) | N3B—C28B—C29B—C30B | −160.6 (3) |
C27A—C28A—C29A—C30A | 84.1 (4) | C27B—C28B—C29B—C30B | 84.6 (4) |
C34A—C29A—C30A—C31A | 1.7 (6) | C34B—C29B—C30B—C31B | 1.3 (6) |
C28A—C29A—C30A—C31A | −177.3 (4) | C28B—C29B—C30B—C31B | −177.7 (4) |
C29A—C30A—C31A—C32A | −0.4 (7) | C29B—C30B—C31B—C32B | −0.5 (7) |
C30A—C31A—C32A—C33A | −1.1 (8) | C30B—C31B—C32B—C33B | −0.6 (7) |
C31A—C32A—C33A—C34A | 1.3 (8) | C31B—C32B—C33B—C34B | 0.9 (8) |
C30A—C29A—C34A—C33A | −1.4 (6) | C30B—C29B—C34B—C33B | −1.0 (6) |
C28A—C29A—C34A—C33A | 177.5 (4) | C28B—C29B—C34B—C33B | 178.0 (4) |
C32A—C33A—C34A—C29A | 0.0 (7) | C32B—C33B—C34B—C29B | −0.1 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O7Ai | 0.89 | 1.90 | 2.768 (4) | 166 |
N1A—H1B···Cl1ii | 0.89 | 2.22 | 3.110 (4) | 174 |
N1A—H1C···O7Biii | 0.89 | 2.36 | 3.086 (4) | 139 |
N1A—H1C···N1B | 0.89 | 2.51 | 3.008 (4) | 116 |
N1B—H1D···O7Biii | 0.86 | 2.23 | 2.980 (4) | 145 |
N1B—H1E···Cl1ii | 0.86 | 2.66 | 3.502 (4) | 166 |
N3A—H3A···Cl1iv | 0.86 | 2.32 | 3.106 (3) | 153 |
N3B—H3B···Cl1 | 0.86 | 2.33 | 3.103 (3) | 150 |
C18A—H18A···O8Av | 0.97 | 2.55 | 3.018 (4) | 109 |
C19A—H19B···O8Av | 0.97 | 2.85 | 3.336 (5) | 112 |
C27A—H27A···O5Avi | 0.97 | 2.48 | 2.935 (4) | 109 |
C28A—H28A···O5Avi | 0.98 | 2.64 | 3.158 (5) | 113 |
C18B—H18C···O8Bv | 0.97 | 2.44 | 3.123 (5) | 127 |
C19B—H19D···O8Bv | 0.97 | 2.78 | 3.351 (5) | 118 |
C27B—H27C···O5Bvi | 0.97 | 2.46 | 2.919 (4) | 109 |
C28B—H28B···O5Bvi | 0.98 | 2.57 | 3.095 (5) | 113 |
Symmetry codes: (i) −x+1, y, −z−1; (ii) −x+1, y+1, −z; (iii) −x+1, y, −z; (iv) x, y, z−1; (v) x, y+1, z; (vi) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C24H23N4O4S+·Cl−·C24H22N4O4S |
Mr | 961.49 |
Crystal system, space group | Monoclinic, C2 |
Temperature (K) | 294 |
a, b, c (Å) | 28.945 (3), 6.5473 (9), 27.526 (2) |
β (°) | 117.622 (7) |
V (Å3) | 4621.9 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.43 × 0.40 × 0.33 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.905, 0.926 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8420, 8252, 5916 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.598 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.116, 1.02 |
No. of reflections | 8252 |
No. of parameters | 605 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.28, −0.18 |
Absolute structure | (Flack, 1983) |
Absolute structure parameter | −0.07 (7) |
Computer programs: CAD-4 EXPRESS (Enraf Nonius, 1994), CAD-4 EXPRESS, XCAD4 (Harms & Wocadlo, 1995), WinGX (Farrugia, 1998), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Johnson et al., 1998), WinGX.
S1A—N4A | 1.660 (3) | S1B—N4B | 1.670 (3) |
S1A—C24A | 1.763 (3) | S1B—C24B | 1.748 (3) |
N1A—C11A | 1.475 (4) | N1B—C11B | 1.388 (5) |
N2A—C17A | 1.368 (5) | N2B—C17B | 1.382 (5) |
N3A—C26A | 1.314 (5) | N3B—C26B | 1.318 (5) |
N3A—C28A | 1.452 (5) | N3B—C28B | 1.452 (4) |
N4A—C26A | 1.402 (4) | N4B—C26B | 1.402 (4) |
N4A—C27A | 1.457 (4) | N4B—C27B | 1.454 (4) |
O7A—C26A | 1.230 (4) | O7B—C26B | 1.229 (4) |
O8A—C17A | 1.221 (4) | O8B—C17B | 1.222 (4) |
C14A—C17A | 1.503 (5) | C14B—C17B | 1.485 (5) |
N2A—C18A—C19A | 103.4 (3) | N2B—C18B—C19B | 105.3 (3) |
C21A—N2A—C17A—O8A | −7.0 (6) | C21B—N2B—C17B—O8B | −4.1 (6) |
C18A—N2A—C17A—C14A | −26.8 (5) | C18B—N2B—C17B—C14B | −22.9 (6) |
C21A—N2A—C17A—C14A | 169.7 (3) | C21B—N2B—C17B—C14B | 176.1 (3) |
C13A—C14A—C17A—O8A | −31.4 (5) | C13B—C14B—C17B—O8B | −30.0 (6) |
C17A—N2A—C18A—C19A | −141.4 (4) | C17B—N2B—C18B—C19B | −153.4 (3) |
C21A—N2A—C18A—C19A | 24.3 (4) | C21B—N2B—C18B—C19B | 9.8 (4) |
N2A—C18A—C19A—C20A | −24.8 (4) | N2B—C18B—C19B—C20B | −9.3 (4) |
C18A—C19A—C20A—C21A | 18.2 (4) | C18B—C19B—C20B—C21B | 5.9 (4) |
C18A—C19A—C20A—C25A | −161.6 (4) | C18B—C19B—C20B—C25B | −173.7 (4) |
C18A—N2A—C21A—C20A | −13.5 (4) | C18B—N2B—C21B—C20B | −6.4 (4) |
C18A—N2A—C21A—C22A | 162.7 (4) | C18B—N2B—C21B—C22B | 170.9 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O7Ai | 0.89 | 1.90 | 2.768 (4) | 166 |
N1A—H1B···Cl1ii | 0.89 | 2.22 | 3.110 (4) | 174 |
N1A—H1C···O7Biii | 0.89 | 2.36 | 3.086 (4) | 139 |
N1A—H1C···N1B | 0.89 | 2.51 | 3.008 (4) | 116 |
N1B—H1D···O7Biii | 0.86 | 2.23 | 2.980 (4) | 145 |
N1B—H1E···Cl1ii | 0.86 | 2.66 | 3.502 (4) | 166 |
N3A—H3A···Cl1iv | 0.86 | 2.32 | 3.106 (3) | 153 |
N3B—H3B···Cl1 | 0.86 | 2.33 | 3.103 (3) | 150 |
C18A—H18A···O8Av | 0.97 | 2.55 | 3.018 (4) | 109 |
C19A—H19B···O8Av | 0.97 | 2.85 | 3.336 (5) | 112 |
C27A—H27A···O5Avi | 0.97 | 2.48 | 2.935 (4) | 109 |
C28A—H28A···O5Avi | 0.98 | 2.64 | 3.158 (5) | 113 |
C18B—H18C···O8Bv | 0.97 | 2.44 | 3.123 (5) | 127 |
C19B—H19D···O8Bv | 0.97 | 2.78 | 3.351 (5) | 118 |
C27B—H27C···O5Bvi | 0.97 | 2.46 | 2.919 (4) | 109 |
C28B—H28B···O5Bvi | 0.98 | 2.57 | 3.095 (5) | 113 |
Symmetry codes: (i) −x+1, y, −z−1; (ii) −x+1, y+1, −z; (iii) −x+1, y, −z; (iv) x, y, z−1; (v) x, y+1, z; (vi) x, y−1, z. |
In the search for new anticancer agents, the free amine of the title compound, (I), was synthesized originally as a racemic mixture (Jung et al., 1998) with only the S enantiomer showing improved antitumor activity (Jung, 1999). Treatment of the free amine with anhydrous HCl/CH3OH solvent and recrystallization from a CH3OH/CH2Cl2 solution unexpectedly produced single crystals of the 2:1 hydrochloride salt. A 1:1 salt, however, could be formed, but only as an amorphous powder. Attempts to obtain a stoichiometric single-crystal of the 1:1 salt from various solvents have thus far failed. The present X-ray crystallographic study was undertaken in order to elucidate the structural characteristics of the 2:1 hydrochloride salt.
In the crystal structure, there exist two conformationally different molecules (A and B in Fig. 1). The Cl1···N1A/B distances are 3.110 (4) and 3.502 (4) Å in A and B, respectively. In addition, the bond lengths of the terminal amine N1A/B to the aromatic ring differ [N1A—C11A 1.475 (4) Å and N1B—C11B 1.388 (5) Å], indicating that molecule A is protonated as NH3+ and molecule B exists in the free NH2 amine form. In the solid-state IR spectrum, both NH3+ and NH2 stretching vibrations were identified; difference Fourier synthesis also verified the existence three and two H atoms at N1A and N1B, respectively. The torsion angles between the three aromatic rings differ in molecules A and B, as depicted in Fig. 2. The major differences are observed in the orientation of the terminal aniline group in comparison to the rest of the molecule. The angles of the N-substituted C6 ring to the terminal phenyl-ring plane are 67.69 (14)° in A and 61.16 (15)° in B, while the indoline groups are oriented at angles of 68.22 (13) and 60.38 (14)° to the former plane in A and B, respectively. In the indoline group, both conformers differ (torsion angles in Table 1), with the C18B atom lying closer to the indoline ring plane in B [C18A—C19A—C20A—C25A −161.6 (4)° and C18B—C19B—C20B—C25B −173.7 (4)°].
The carbonyl plane is twisted from the phenyl plane in both conformations [C13A—C14A—C17A—O8A −31.4 (5)° and C13B—C14B—C17B—O8B −30.0 (6)°]. The longer Csp2—Csp2 bond lengths [C14A—C17A 1.503 (5) Å and C14B—C17B 1.485 (5) Å] arise from the deviation from coplanarity of the amide carbonyl and phenyl-ring systems. The two amide groups of each molecule show a characteristic feature in both conformations. The former C—N bonds are shorter than the normal amide C—N bonds [N2A—C17A 1.368 (5) Å and N2B—C17B 1.382 (5) Å] attached to indoline ring. The lengths of the two amide C—N bonds of the imidazolone ring differ with the short N3A—C26A [1.314 (5) Å] and N3B—C26B [1.318 (5) Å] bonds having double-bond character compared with the longer N4A—C26A [1.402 (4) Å] and N4B—C26B [1.402 (4) Å] bonds on the opposite side of urea group.
The hydrogen-bonding parameters listed in Table 2 reveal the differences in the intermolecular relationships of the two molecules on packing. The distance of the terminal N atom to the central Cl1 ion shows remarkable inequality, with N1Aii···Cl1 [3.110 (4) Å; symmetry code: (ii) 1 − x, −1 + y, −z] substantially shorter than N1Bii···Cl1 [3.502 (4) Å]. The former constitutes a hydrogen bond, whereas the latter resides at the edge of conventional hydrogen bonds. All imidazolone NH groups in A and B act as donors to the Cl1 ion, forming hydrogen bonds of similar strength and geometry [N3Ai···Cl1 3.106 (3) Å and N3B···Cl1 3.103 (3) Å]. Thus, the Cl ion is a fourfold acceptor, accepting two from the N1Aii and N1Bii terminal amines and two from the N3Ai and N3B atoms of the imidazolone groups of molecules A and B [symmetry code: (i) x, y, 1 + z]. The N1Aii, N3Ai and N3B atoms and the Cl1 ion are almost coplanar and perpendicular to the c axis, resulting in a `hydrogen-bonding channel' parallel to the c axis. The increased anisotropy of the N3A and N3B atoms may be due to the inherent loose packing through this channel with the Cl ion as an acceptor of hydrogen in the centre showing a synchronous positional disorder and atomic mobility in this direction.
As well as the four hydrogen bonds to the Cl1 ion, four more hydrogen bonds involving the N—H groups and O atoms of the imidazolone contribute to crystalline cohesion. N1Aiii donates its H1Aiii and H1Ciii atoms to the carbonyl O7Ai and O7B atom of the imidazolone, and N1Biii interacts with the neighbouring N1Aiii and O7B atoms [symmetry code: (iii) 1 − x, y, −z]. The O7B and N1Biii acceptors share H1Ciii from N1Aiii, thus building a three-centre hydrogen bond, and O7B is an acceptor of two H atoms from N1Aiii and N1Biii. In Fig. 3, all the hydrogen bonds around the Cl ion are shown explicitly. Furthermore, additional multi-centre interactions involving aliphatic C—H groups of A and B are present. These are depicted in Fig. 4 and listed in Table 2.