Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805027595/ci6618sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805027595/ci6618Isup2.hkl |
CCDC reference: 278140
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.052
- wR factor = 0.156
- Data-to-parameter ratio = 17.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.57 Ratio PLAT301_ALERT_3_C Main Residue Disorder ......................... 5.00 Perc. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 1 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
6-Methyl-4-amino-5-ethoxycarbonyltetrahydrobenzo[4,5]thieno[3,2;5,6]pyridine was prepared according to the literature procedure (Veronese et al., 1995) in 64% yield. Iminophosphorane was also synthesized according to a literature method (Wamhoff et al., 1993) in 93% yield. To a solution of iminophosphorane (0.525 g, 1 mmol) in anhydrous CH2Cl2 (10 ml) was added aromatic isocyanate (1.1 mmol) under N2 atmosphere at room temperature. The reaction mixture was left unstirred for 5 h, and then the solvent was removed under reduced pressure and Et2O/petroleum ether was added to precipitate triphenylphosphine oxide. Removal of the solvent gave carbodiimide, which was used directly without further purification. To the solution of carbodiimide prepared above in CH2Cl2 (10 ml) was added n-propylamine (1.1 mmol). The reaction mixture was stirred for 30 min, and then the solvent was removed and anhydrous ethanol (10 ml) with several drops of CH3CH2ONa in CH3CH2OH was added. The mixture was stirred for 11 h at room temperature, the solution was condensed and the residue was recrystallized from CH3CH2OH to give the title compound. Single crystals were obtained by evaporation of methanol solution (m.p. 501–503 K). Analysis calculated for C23H23ClN4OS: C 62.93, H 5.28, N 12.76%; found: C 63.26, H 5.23, N 12.45%. 1H NMR (CDCl3, TMS, 400 MHz): δ 0.91 (t, J = 7.2 Hz, 3H, CH3), 1.62 (q, J = 7.2 Hz, 2H, CH2), 1.92 (s, 4H, 2CH2), 2.87 (s, 2H, CH2), 2.94 (s, 3H, CH3 of pyridyl), 3.29 (s, 2H, CH2), 3.44 (m, 2H, NCH2), 4.41 (s, 1H, NH), 7.27–7.60 (m, 4H, Ar—H). MS (EI, m/z, %): 439 (M++1 35.14), 438 (100), 398 (14.08), 396 (17.21), 395 (24.23), 110 (15.44).
In one of the independent molecules, the propylamine group is disordered over two orientations with occupancies of 0.515 (8) and 0.485 (8). The disorder was modelled with C—C and C···C distances of 1.54 and 2.51 Å, respectively. All the H atoms were placed in idealized positions and constrained to ride on their parent atoms, with N—H = 0.86 and 0.90 Å, C—H = 0.93–0.97 Å, and with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C,N) for other H atoms.
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
Fig. 1. The asymmetric unit of (I), showing 50% probability displacement ellipsoids. Both components of the disordered propylamine group are shown. |
C23H23ClN4OS | Z = 4 |
Mr = 438.96 | F(000) = 920 |
Triclinic, P1 | Dx = 1.344 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.8884 (6) Å | Cell parameters from 3870 reflections |
b = 13.3784 (7) Å | θ = 2.3–26.9° |
c = 15.7892 (8) Å | µ = 0.30 mm−1 |
α = 114.054 (1)° | T = 292 K |
β = 98.926 (1)° | Block, colourless |
γ = 101.335 (1)° | 0.40 × 0.30 × 0.30 mm |
V = 2169.42 (19) Å3 |
Bruker SMART CCD area-detector diffractometer | 9849 independent reflections |
Radiation source: fine-focus sealed tube | 6468 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
ϕ and ω scans | θmax = 27.5°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −15→15 |
Tmin = 0.891, Tmax = 0.917 | k = −17→17 |
25134 measured reflections | l = −20→20 |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.156 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0778P)2 + 0.1323P] where P = (Fo2 + 2Fc2)/3 |
9849 reflections | (Δ/σ)max = 0.001 |
574 parameters | Δρmax = 0.32 e Å−3 |
7 restraints | Δρmin = −0.21 e Å−3 |
C23H23ClN4OS | γ = 101.335 (1)° |
Mr = 438.96 | V = 2169.42 (19) Å3 |
Triclinic, P1 | Z = 4 |
a = 11.8884 (6) Å | Mo Kα radiation |
b = 13.3784 (7) Å | µ = 0.30 mm−1 |
c = 15.7892 (8) Å | T = 292 K |
α = 114.054 (1)° | 0.40 × 0.30 × 0.30 mm |
β = 98.926 (1)° |
Bruker SMART CCD area-detector diffractometer | 9849 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 6468 reflections with I > 2σ(I) |
Tmin = 0.891, Tmax = 0.917 | Rint = 0.040 |
25134 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 7 restraints |
wR(F2) = 0.156 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.32 e Å−3 |
9849 reflections | Δρmin = −0.21 e Å−3 |
574 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.83965 (7) | 0.78315 (6) | 0.38004 (4) | 0.0676 (2) | |
Cl1 | 0.69608 (9) | −0.01047 (6) | −0.43385 (5) | 0.0987 (3) | |
O1 | 0.75577 (16) | 0.26620 (13) | 0.01717 (11) | 0.0590 (4) | |
N1 | 0.77021 (15) | 0.38157 (14) | −0.05490 (12) | 0.0424 (4) | |
N2 | 0.81663 (15) | 0.58305 (14) | 0.03154 (12) | 0.0431 (4) | |
N3 | 0.79331 (16) | 0.49906 (15) | −0.13039 (12) | 0.0482 (4) | |
H3 | 0.7750 | 0.4378 | −0.1838 | 0.058* | |
N4 | 0.79378 (17) | 0.55450 (16) | 0.28406 (13) | 0.0506 (5) | |
C1 | 0.79393 (17) | 0.49006 (17) | −0.04908 (14) | 0.0404 (5) | |
C2 | 0.76997 (18) | 0.36276 (18) | 0.02714 (15) | 0.0427 (5) | |
C3 | 0.78741 (17) | 0.46588 (17) | 0.11601 (14) | 0.0411 (5) | |
C4 | 0.81125 (17) | 0.57168 (17) | 0.11311 (14) | 0.0396 (5) | |
C5 | 0.78045 (18) | 0.46055 (18) | 0.20347 (15) | 0.0448 (5) | |
C6 | 0.7560 (2) | 0.3517 (2) | 0.21206 (17) | 0.0582 (6) | |
H6A | 0.7439 | 0.3665 | 0.2743 | 0.087* | |
H6B | 0.8225 | 0.3212 | 0.2043 | 0.087* | |
H6C | 0.6860 | 0.2976 | 0.1632 | 0.087* | |
C7 | 0.81831 (19) | 0.65471 (19) | 0.27952 (15) | 0.0486 (5) | |
C8 | 0.82894 (18) | 0.67145 (18) | 0.19942 (14) | 0.0432 (5) | |
C9 | 0.85478 (18) | 0.79069 (18) | 0.22070 (15) | 0.0461 (5) | |
C10 | 0.8729 (2) | 0.84047 (19) | 0.15200 (17) | 0.0527 (6) | |
H10A | 0.8099 | 0.7967 | 0.0929 | 0.063* | |
H10B | 0.9479 | 0.8345 | 0.1364 | 0.063* | |
C11 | 0.8735 (3) | 0.9652 (2) | 0.1946 (2) | 0.0797 (8) | |
H11A | 0.9088 | 1.0000 | 0.1581 | 0.096* | |
H11B | 0.7920 | 0.9685 | 0.1876 | 0.096* | |
C12 | 0.9395 (3) | 1.0330 (2) | 0.2976 (2) | 0.0866 (9) | |
H12A | 0.9361 | 1.1112 | 0.3193 | 0.104* | |
H12B | 1.0223 | 1.0343 | 0.3042 | 0.104* | |
C13 | 0.8916 (3) | 0.9870 (2) | 0.3606 (2) | 0.0767 (8) | |
H13A | 0.8201 | 1.0088 | 0.3720 | 0.092* | |
H13B | 0.9497 | 1.0193 | 0.4222 | 0.092* | |
C14 | 0.8632 (2) | 0.8585 (2) | 0.31397 (17) | 0.0581 (6) | |
C15 | 0.75202 (19) | 0.28309 (17) | −0.14585 (14) | 0.0442 (5) | |
C16 | 0.6392 (2) | 0.21056 (19) | −0.19575 (16) | 0.0525 (6) | |
H16 | 0.5751 | 0.2229 | −0.1700 | 0.063* | |
C17 | 0.6219 (2) | 0.1191 (2) | −0.28468 (17) | 0.0616 (7) | |
H17 | 0.5462 | 0.0697 | −0.3192 | 0.074* | |
C18 | 0.7177 (3) | 0.10216 (19) | −0.32121 (16) | 0.0588 (6) | |
C19 | 0.8304 (2) | 0.1727 (2) | −0.27115 (17) | 0.0584 (6) | |
H19 | 0.8946 | 0.1596 | −0.2966 | 0.070* | |
C20 | 0.8474 (2) | 0.2634 (2) | −0.18246 (16) | 0.0520 (6) | |
H20 | 0.9237 | 0.3112 | −0.1474 | 0.062* | |
C21 | 0.82263 (19) | 0.60916 (19) | −0.13101 (16) | 0.0483 (5) | |
H21A | 0.7896 | 0.6604 | −0.0850 | 0.058* | |
H21B | 0.7861 | 0.5997 | −0.1942 | 0.058* | |
C22 | 0.9532 (2) | 0.6620 (2) | −0.1070 (2) | 0.0648 (7) | |
H22A | 0.9859 | 0.6122 | −0.1544 | 0.078* | |
H22B | 0.9903 | 0.6691 | −0.0448 | 0.078* | |
C23 | 0.9826 (3) | 0.7784 (3) | −0.1044 (3) | 0.1018 (11) | |
H23A | 1.0673 | 0.8114 | −0.0844 | 0.153* | |
H23B | 0.9472 | 0.8270 | −0.0598 | 0.153* | |
H23C | 0.9521 | 0.7710 | −0.1673 | 0.153* | |
S1' | 0.59009 (6) | 0.06546 (6) | 0.18901 (4) | 0.06011 (19) | |
Cl1' | 0.53506 (6) | 0.69778 (7) | 1.00401 (4) | 0.0787 (2) | |
O1' | 0.68877 (14) | 0.37945 (15) | 0.66260 (10) | 0.0613 (4) | |
N1' | 0.50461 (15) | 0.38250 (15) | 0.60285 (11) | 0.0429 (4) | |
N2' | 0.40559 (15) | 0.28553 (15) | 0.43701 (12) | 0.0452 (4) | |
N3' | 0.31617 (16) | 0.39209 (18) | 0.54449 (13) | 0.0595 (5) | |
H3'A | 0.3276 | 0.4486 | 0.5999 | 0.071* | 0.515 (8) |
H3'B | 0.3138 | 0.4340 | 0.6052 | 0.071* | 0.485 (8) |
N4' | 0.70662 (17) | 0.17901 (16) | 0.37671 (13) | 0.0516 (5) | |
C1' | 0.40820 (19) | 0.35119 (18) | 0.52575 (14) | 0.0435 (5) | |
C2' | 0.60838 (19) | 0.34809 (18) | 0.59099 (14) | 0.0445 (5) | |
C3' | 0.60749 (18) | 0.27802 (17) | 0.49249 (14) | 0.0409 (5) | |
C4' | 0.50282 (18) | 0.24763 (17) | 0.42087 (14) | 0.0406 (5) | |
C5' | 0.70776 (19) | 0.24138 (19) | 0.46733 (15) | 0.0468 (5) | |
C6' | 0.8233 (2) | 0.2721 (2) | 0.53933 (17) | 0.0619 (6) | |
H6'A | 0.8788 | 0.2404 | 0.5065 | 0.093* | |
H6'B | 0.8098 | 0.2418 | 0.5837 | 0.093* | |
H6'C | 0.8550 | 0.3538 | 0.5738 | 0.093* | |
C7' | 0.6044 (2) | 0.14785 (18) | 0.31009 (15) | 0.0471 (5) | |
C8' | 0.49967 (19) | 0.17450 (17) | 0.32520 (14) | 0.0431 (5) | |
C9' | 0.4048 (2) | 0.12283 (17) | 0.23743 (14) | 0.0448 (5) | |
C10' | 0.2773 (2) | 0.1222 (2) | 0.22841 (16) | 0.0548 (6) | |
H10C | 0.2695 | 0.1955 | 0.2345 | 0.066* | |
H10D | 0.2510 | 0.1102 | 0.2796 | 0.066* | |
C11' | 0.1996 (2) | 0.0268 (2) | 0.13060 (17) | 0.0656 (7) | |
H11C | 0.1944 | −0.0469 | 0.1297 | 0.079* | |
H11D | 0.1199 | 0.0348 | 0.1208 | 0.079* | |
C12' | 0.2512 (3) | 0.0324 (2) | 0.05077 (17) | 0.0712 (8) | |
H12C | 0.2613 | 0.1080 | 0.0545 | 0.085* | |
H12D | 0.1966 | −0.0226 | −0.0108 | 0.085* | |
C13' | 0.3702 (3) | 0.0071 (2) | 0.05733 (16) | 0.0660 (7) | |
H13C | 0.3576 | −0.0747 | 0.0317 | 0.079* | |
H13D | 0.4126 | 0.0335 | 0.0191 | 0.079* | |
C14' | 0.4433 (2) | 0.06570 (18) | 0.16013 (15) | 0.0519 (6) | |
C15' | 0.50559 (18) | 0.45880 (18) | 0.69984 (14) | 0.0411 (5) | |
C16' | 0.4849 (2) | 0.4146 (2) | 0.76316 (15) | 0.0491 (5) | |
H16A | 0.4655 | 0.3361 | 0.7426 | 0.059* | |
C17' | 0.4934 (2) | 0.4883 (2) | 0.85735 (16) | 0.0537 (6) | |
H17A | 0.4809 | 0.4602 | 0.9012 | 0.064* | |
C18' | 0.52042 (19) | 0.6032 (2) | 0.88507 (15) | 0.0490 (5) | |
C19' | 0.53746 (19) | 0.64733 (19) | 0.82174 (16) | 0.0505 (5) | |
H19A | 0.5532 | 0.7255 | 0.8417 | 0.061* | |
C20' | 0.53092 (19) | 0.57393 (19) | 0.72802 (15) | 0.0468 (5) | |
H20A | 0.5436 | 0.6024 | 0.6844 | 0.056* | |
C21' | 0.1968 (5) | 0.3482 (7) | 0.4780 (5) | 0.053 (2) | 0.515 (8) |
H21C | 0.1361 | 0.3497 | 0.5126 | 0.063* | 0.515 (8) |
H21D | 0.1836 | 0.2703 | 0.4300 | 0.063* | 0.515 (8) |
C22' | 0.1936 (6) | 0.4259 (5) | 0.4315 (5) | 0.075 (2) | 0.515 (8) |
H22C | 0.2507 | 0.4193 | 0.3932 | 0.090* | 0.515 (8) |
H22D | 0.2153 | 0.5045 | 0.4807 | 0.090* | 0.515 (8) |
C23' | 0.0679 (8) | 0.3939 (10) | 0.3669 (6) | 0.093 (3) | 0.515 (8) |
H23D | 0.0721 | 0.4232 | 0.3209 | 0.140* | 0.515 (8) |
H23E | 0.0176 | 0.4263 | 0.4059 | 0.140* | 0.515 (8) |
H23F | 0.0357 | 0.3122 | 0.3339 | 0.140* | 0.515 (8) |
C21A | 0.2202 (6) | 0.3681 (10) | 0.4607 (5) | 0.066 (3) | 0.485 (8) |
H21E | 0.1756 | 0.2879 | 0.4307 | 0.079* | 0.485 (8) |
H21F | 0.2557 | 0.3825 | 0.4139 | 0.079* | 0.485 (8) |
C22A | 0.1364 (6) | 0.4392 (6) | 0.4871 (5) | 0.082 (3) | 0.485 (8) |
H22E | 0.1784 | 0.5187 | 0.5082 | 0.098* | 0.485 (8) |
H22F | 0.1096 | 0.4335 | 0.5404 | 0.098* | 0.485 (8) |
C23A | 0.0286 (8) | 0.4018 (11) | 0.4032 (6) | 0.093 (3) | 0.485 (8) |
H23G | 0.0117 | 0.4680 | 0.4009 | 0.139* | 0.485 (8) |
H23H | −0.0388 | 0.3577 | 0.4118 | 0.139* | 0.485 (8) |
H23I | 0.0452 | 0.3560 | 0.3442 | 0.139* | 0.485 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0945 (5) | 0.0549 (4) | 0.0385 (3) | 0.0194 (3) | 0.0211 (3) | 0.0066 (3) |
Cl1 | 0.1573 (8) | 0.0568 (4) | 0.0531 (4) | 0.0172 (5) | 0.0377 (5) | 0.0000 (3) |
O1 | 0.0837 (12) | 0.0400 (9) | 0.0488 (9) | 0.0175 (8) | 0.0143 (8) | 0.0172 (7) |
N1 | 0.0470 (10) | 0.0381 (9) | 0.0340 (9) | 0.0107 (8) | 0.0098 (7) | 0.0098 (7) |
N2 | 0.0474 (10) | 0.0399 (9) | 0.0347 (9) | 0.0103 (8) | 0.0089 (8) | 0.0116 (7) |
N3 | 0.0598 (11) | 0.0413 (10) | 0.0331 (9) | 0.0102 (8) | 0.0091 (8) | 0.0100 (8) |
N4 | 0.0592 (12) | 0.0526 (11) | 0.0372 (10) | 0.0166 (9) | 0.0153 (8) | 0.0165 (8) |
C1 | 0.0373 (11) | 0.0427 (12) | 0.0363 (11) | 0.0115 (9) | 0.0086 (8) | 0.0137 (9) |
C2 | 0.0414 (11) | 0.0436 (12) | 0.0380 (11) | 0.0117 (9) | 0.0089 (9) | 0.0144 (9) |
C3 | 0.0386 (11) | 0.0420 (11) | 0.0376 (11) | 0.0122 (9) | 0.0086 (9) | 0.0133 (9) |
C4 | 0.0344 (10) | 0.0441 (11) | 0.0350 (10) | 0.0119 (9) | 0.0094 (8) | 0.0126 (9) |
C5 | 0.0431 (12) | 0.0494 (13) | 0.0413 (12) | 0.0144 (10) | 0.0122 (9) | 0.0190 (10) |
C6 | 0.0693 (16) | 0.0588 (15) | 0.0528 (14) | 0.0196 (12) | 0.0182 (12) | 0.0301 (12) |
C7 | 0.0499 (13) | 0.0481 (13) | 0.0392 (12) | 0.0152 (10) | 0.0128 (10) | 0.0109 (10) |
C8 | 0.0386 (11) | 0.0455 (12) | 0.0377 (11) | 0.0125 (9) | 0.0084 (9) | 0.0120 (9) |
C9 | 0.0423 (12) | 0.0433 (12) | 0.0431 (12) | 0.0138 (9) | 0.0089 (9) | 0.0106 (9) |
C10 | 0.0568 (14) | 0.0456 (13) | 0.0502 (13) | 0.0163 (11) | 0.0105 (11) | 0.0170 (11) |
C11 | 0.107 (2) | 0.0544 (16) | 0.075 (2) | 0.0286 (16) | 0.0181 (17) | 0.0260 (15) |
C12 | 0.116 (3) | 0.0425 (15) | 0.080 (2) | 0.0169 (16) | 0.0170 (19) | 0.0136 (15) |
C13 | 0.103 (2) | 0.0465 (14) | 0.0584 (16) | 0.0235 (14) | 0.0149 (15) | 0.0041 (12) |
C14 | 0.0661 (15) | 0.0491 (13) | 0.0463 (13) | 0.0180 (11) | 0.0136 (11) | 0.0093 (11) |
C15 | 0.0534 (13) | 0.0387 (11) | 0.0349 (11) | 0.0149 (10) | 0.0108 (9) | 0.0110 (9) |
C16 | 0.0538 (14) | 0.0472 (13) | 0.0462 (13) | 0.0101 (11) | 0.0142 (11) | 0.0131 (10) |
C17 | 0.0723 (17) | 0.0462 (13) | 0.0443 (13) | 0.0017 (12) | 0.0076 (12) | 0.0093 (11) |
C18 | 0.0904 (19) | 0.0419 (13) | 0.0379 (12) | 0.0188 (13) | 0.0186 (13) | 0.0116 (10) |
C19 | 0.0725 (17) | 0.0579 (15) | 0.0522 (14) | 0.0322 (13) | 0.0271 (13) | 0.0222 (12) |
C20 | 0.0504 (13) | 0.0530 (13) | 0.0457 (12) | 0.0187 (11) | 0.0110 (10) | 0.0148 (11) |
C21 | 0.0514 (13) | 0.0503 (13) | 0.0422 (12) | 0.0170 (10) | 0.0092 (10) | 0.0201 (10) |
C22 | 0.0522 (14) | 0.0619 (16) | 0.0768 (18) | 0.0148 (12) | 0.0137 (13) | 0.0299 (14) |
C23 | 0.086 (2) | 0.0644 (19) | 0.151 (3) | 0.0082 (16) | 0.033 (2) | 0.050 (2) |
S1' | 0.0759 (4) | 0.0615 (4) | 0.0376 (3) | 0.0271 (3) | 0.0212 (3) | 0.0118 (3) |
Cl1' | 0.0739 (4) | 0.0941 (5) | 0.0372 (3) | 0.0200 (4) | 0.0176 (3) | 0.0013 (3) |
O1' | 0.0541 (9) | 0.0815 (12) | 0.0332 (8) | 0.0281 (8) | 0.0026 (7) | 0.0110 (8) |
N1' | 0.0465 (10) | 0.0477 (10) | 0.0294 (8) | 0.0150 (8) | 0.0089 (7) | 0.0125 (7) |
N2' | 0.0462 (10) | 0.0506 (10) | 0.0317 (9) | 0.0168 (8) | 0.0073 (7) | 0.0118 (8) |
N3' | 0.0486 (11) | 0.0744 (14) | 0.0386 (10) | 0.0275 (10) | 0.0073 (9) | 0.0069 (9) |
N4' | 0.0576 (12) | 0.0552 (11) | 0.0408 (10) | 0.0227 (9) | 0.0157 (9) | 0.0166 (9) |
C1' | 0.0465 (12) | 0.0459 (12) | 0.0338 (11) | 0.0135 (10) | 0.0076 (9) | 0.0147 (9) |
C2' | 0.0489 (12) | 0.0456 (12) | 0.0349 (11) | 0.0157 (10) | 0.0090 (10) | 0.0139 (9) |
C3' | 0.0468 (12) | 0.0418 (11) | 0.0321 (10) | 0.0140 (9) | 0.0086 (9) | 0.0149 (9) |
C4' | 0.0479 (12) | 0.0393 (11) | 0.0334 (10) | 0.0116 (9) | 0.0105 (9) | 0.0156 (9) |
C5' | 0.0515 (13) | 0.0490 (12) | 0.0413 (12) | 0.0186 (10) | 0.0122 (10) | 0.0200 (10) |
C6' | 0.0545 (14) | 0.0763 (17) | 0.0527 (14) | 0.0294 (13) | 0.0107 (11) | 0.0236 (13) |
C7' | 0.0599 (14) | 0.0444 (12) | 0.0375 (11) | 0.0185 (10) | 0.0170 (10) | 0.0158 (9) |
C8' | 0.0556 (13) | 0.0383 (11) | 0.0329 (10) | 0.0126 (10) | 0.0123 (9) | 0.0139 (9) |
C9' | 0.0594 (14) | 0.0381 (11) | 0.0308 (10) | 0.0129 (10) | 0.0094 (9) | 0.0112 (9) |
C10' | 0.0577 (14) | 0.0562 (14) | 0.0388 (12) | 0.0109 (11) | 0.0051 (10) | 0.0158 (11) |
C11' | 0.0641 (16) | 0.0611 (15) | 0.0478 (14) | −0.0001 (12) | −0.0009 (12) | 0.0158 (12) |
C12' | 0.0810 (19) | 0.0653 (16) | 0.0374 (13) | −0.0068 (14) | −0.0068 (12) | 0.0153 (12) |
C13' | 0.0863 (19) | 0.0564 (15) | 0.0351 (12) | 0.0093 (13) | 0.0094 (12) | 0.0089 (11) |
C14' | 0.0714 (15) | 0.0423 (12) | 0.0345 (11) | 0.0131 (11) | 0.0134 (10) | 0.0118 (9) |
C15' | 0.0430 (11) | 0.0460 (12) | 0.0292 (10) | 0.0144 (9) | 0.0086 (8) | 0.0118 (9) |
C16' | 0.0566 (13) | 0.0495 (13) | 0.0416 (12) | 0.0176 (11) | 0.0130 (10) | 0.0199 (10) |
C17' | 0.0574 (14) | 0.0721 (17) | 0.0358 (12) | 0.0207 (12) | 0.0160 (10) | 0.0263 (11) |
C18' | 0.0417 (12) | 0.0603 (15) | 0.0338 (11) | 0.0145 (10) | 0.0103 (9) | 0.0106 (10) |
C19' | 0.0477 (13) | 0.0440 (12) | 0.0465 (13) | 0.0094 (10) | 0.0118 (10) | 0.0100 (10) |
C20' | 0.0517 (13) | 0.0496 (13) | 0.0380 (11) | 0.0130 (10) | 0.0127 (10) | 0.0192 (10) |
C21' | 0.055 (4) | 0.056 (3) | 0.039 (3) | 0.012 (3) | 0.022 (3) | 0.012 (3) |
C22' | 0.087 (5) | 0.073 (4) | 0.065 (4) | 0.024 (3) | 0.007 (3) | 0.034 (3) |
C23' | 0.092 (6) | 0.111 (6) | 0.069 (5) | 0.024 (5) | −0.010 (4) | 0.047 (5) |
C21A | 0.043 (4) | 0.109 (8) | 0.045 (4) | 0.039 (4) | 0.015 (3) | 0.024 (4) |
C22A | 0.073 (4) | 0.100 (5) | 0.059 (4) | 0.041 (4) | 0.002 (3) | 0.023 (3) |
C23A | 0.077 (5) | 0.134 (8) | 0.077 (6) | 0.041 (5) | 0.002 (4) | 0.059 (6) |
S1—C7 | 1.737 (2) | N1'—C15' | 1.450 (2) |
S1—C14 | 1.738 (3) | N2'—C1' | 1.307 (2) |
Cl1—C18 | 1.738 (2) | N2'—C4' | 1.369 (3) |
O1—C2 | 1.209 (2) | N3'—C1' | 1.337 (3) |
N1—C1 | 1.384 (3) | N3'—C21' | 1.473 (6) |
N1—C2 | 1.417 (3) | N3'—C21A | 1.483 (6) |
N1—C15 | 1.447 (2) | N3'—H3'A | 0.86 |
N2—C1 | 1.308 (2) | N3'—H3'B | 0.90 |
N2—C4 | 1.367 (3) | N4'—C5' | 1.327 (3) |
N3—C1 | 1.337 (3) | N4'—C7' | 1.343 (3) |
N3—C21 | 1.450 (3) | C2'—C3' | 1.449 (3) |
N3—H3 | 0.86 | C3'—C4' | 1.408 (3) |
N4—C5 | 1.334 (3) | C3'—C5' | 1.427 (3) |
N4—C7 | 1.349 (3) | C4'—C8' | 1.415 (3) |
C2—C3 | 1.461 (3) | C5'—C6' | 1.503 (3) |
C3—C4 | 1.409 (3) | C6'—H6'A | 0.96 |
C3—C5 | 1.426 (3) | C6'—H6'B | 0.96 |
C4—C8 | 1.414 (3) | C6'—H6'C | 0.96 |
C5—C6 | 1.493 (3) | C7'—C8' | 1.390 (3) |
C6—H6A | 0.96 | C8'—C9' | 1.448 (3) |
C6—H6B | 0.96 | C9'—C14' | 1.353 (3) |
C6—H6C | 0.96 | C9'—C10' | 1.498 (3) |
C7—C8 | 1.391 (3) | C10'—C11' | 1.535 (3) |
C8—C9 | 1.446 (3) | C10'—H10C | 0.97 |
C9—C14 | 1.353 (3) | C10'—H10D | 0.97 |
C9—C10 | 1.507 (3) | C11'—C12' | 1.507 (4) |
C10—C11 | 1.522 (3) | C11'—H11C | 0.97 |
C10—H10A | 0.97 | C11'—H11D | 0.97 |
C10—H10B | 0.97 | C12'—C13' | 1.515 (4) |
C11—C12 | 1.486 (4) | C12'—H12C | 0.97 |
C11—H11A | 0.97 | C12'—H12D | 0.97 |
C11—H11B | 0.97 | C13'—C14' | 1.504 (3) |
C12—C13 | 1.494 (4) | C13'—H13C | 0.97 |
C12—H12A | 0.97 | C13'—H13D | 0.97 |
C12—H12B | 0.97 | C15'—C20' | 1.371 (3) |
C13—C14 | 1.508 (3) | C15'—C16' | 1.382 (3) |
C13—H13A | 0.97 | C16'—C17' | 1.383 (3) |
C13—H13B | 0.97 | C16'—H16A | 0.93 |
C15—C20 | 1.374 (3) | C17'—C18' | 1.368 (3) |
C15—C16 | 1.378 (3) | C17'—H17A | 0.93 |
C16—C17 | 1.387 (3) | C18'—C19' | 1.373 (3) |
C16—H16 | 0.93 | C19'—C20' | 1.382 (3) |
C17—C18 | 1.371 (4) | C19'—H19A | 0.93 |
C17—H17 | 0.93 | C20'—H20A | 0.93 |
C18—C19 | 1.370 (4) | C21'—C22' | 1.499 (7) |
C19—C20 | 1.380 (3) | C21'—H21C | 0.97 |
C19—H19 | 0.93 | C21'—H21D | 0.97 |
C20—H20 | 0.93 | C22'—C23' | 1.541 (7) |
C21—C22 | 1.490 (3) | C22'—H22C | 0.97 |
C21—H21A | 0.97 | C22'—H22D | 0.97 |
C21—H21B | 0.97 | C23'—H23D | 0.96 |
C22—C23 | 1.510 (4) | C23'—H23E | 0.96 |
C22—H22A | 0.97 | C23'—H23F | 0.96 |
C22—H22B | 0.97 | C21A—C22A | 1.500 (8) |
C23—H23A | 0.96 | C21A—H21E | 0.97 |
C23—H23B | 0.96 | C21A—H21F | 0.97 |
C23—H23C | 0.96 | C22A—C23A | 1.525 (7) |
S1'—C7' | 1.734 (2) | C22A—H22E | 0.97 |
S1'—C14' | 1.735 (3) | C22A—H22F | 0.97 |
Cl1'—C18' | 1.741 (2) | C23A—H23G | 0.96 |
O1'—C2' | 1.220 (2) | C23A—H23H | 0.96 |
N1'—C1' | 1.391 (3) | C23A—H23I | 0.96 |
N1'—C2' | 1.412 (3) | ||
C7—S1—C14 | 91.00 (11) | C21A—N3'—H3'A | 121.9 |
C1—N1—C2 | 122.21 (17) | C1'—N3'—H3'B | 121.4 |
C1—N1—C15 | 120.14 (16) | C21'—N3'—H3'B | 110.6 |
C2—N1—C15 | 117.55 (16) | C21A—N3'—H3'B | 121.7 |
C1—N2—C4 | 118.07 (18) | C5'—N4'—C7' | 116.56 (18) |
C1—N3—C21 | 121.83 (17) | N2'—C1'—N3' | 119.66 (18) |
C1—N3—H3 | 119.1 | N2'—C1'—N1' | 122.58 (19) |
C21—N3—H3 | 119.1 | N3'—C1'—N1' | 117.75 (18) |
C5—N4—C7 | 116.82 (18) | O1'—C2'—N1' | 118.21 (18) |
N2—C1—N3 | 118.99 (19) | O1'—C2'—C3' | 126.62 (19) |
N2—C1—N1 | 123.28 (18) | N1'—C2'—C3' | 115.17 (17) |
N3—C1—N1 | 117.74 (17) | C4'—C3'—C5' | 120.47 (18) |
O1—C2—N1 | 118.30 (18) | C4'—C3'—C2' | 117.15 (18) |
O1—C2—C3 | 127.29 (19) | C5'—C3'—C2' | 122.38 (18) |
N1—C2—C3 | 114.41 (18) | N2'—C4'—C3' | 124.73 (18) |
C4—C3—C5 | 120.52 (18) | N2'—C4'—C8' | 118.07 (18) |
C4—C3—C2 | 118.07 (18) | C3'—C4'—C8' | 117.19 (19) |
C5—C3—C2 | 121.41 (19) | N4'—C5'—C3' | 121.82 (19) |
N2—C4—C3 | 123.73 (18) | N4'—C5'—C6' | 114.54 (19) |
N2—C4—C8 | 118.32 (18) | C3'—C5'—C6' | 123.62 (19) |
C3—C4—C8 | 117.95 (18) | C5'—C6'—H6'A | 109.5 |
N4—C5—C3 | 121.34 (19) | C5'—C6'—H6'B | 109.5 |
N4—C5—C6 | 115.15 (19) | H6'A—C6'—H6'B | 109.5 |
C3—C5—C6 | 123.50 (19) | C5'—C6'—H6'C | 109.5 |
C5—C6—H6A | 109.5 | H6'A—C6'—H6'C | 109.5 |
C5—C6—H6B | 109.5 | H6'B—C6'—H6'C | 109.5 |
H6A—C6—H6B | 109.5 | N4'—C7'—C8' | 127.31 (19) |
C5—C6—H6C | 109.5 | N4'—C7'—S1' | 121.46 (16) |
H6A—C6—H6C | 109.5 | C8'—C7'—S1' | 111.23 (16) |
H6B—C6—H6C | 109.5 | C7'—C8'—C4' | 116.41 (19) |
N4—C7—C8 | 127.34 (19) | C7'—C8'—C9' | 112.77 (18) |
N4—C7—S1 | 121.17 (17) | C4'—C8'—C9' | 130.8 (2) |
C8—C7—S1 | 111.49 (17) | C14'—C9'—C8' | 111.1 (2) |
C7—C8—C4 | 115.99 (19) | C14'—C9'—C10' | 121.7 (2) |
C7—C8—C9 | 112.30 (19) | C8'—C9'—C10' | 127.08 (18) |
C4—C8—C9 | 131.7 (2) | C9'—C10'—C11' | 110.02 (19) |
C14—C9—C8 | 111.9 (2) | C9'—C10'—H10C | 109.7 |
C14—C9—C10 | 121.1 (2) | C11'—C10'—H10C | 109.7 |
C8—C9—C10 | 126.98 (19) | C9'—C10'—H10D | 109.7 |
C9—C10—C11 | 111.6 (2) | C11'—C10'—H10D | 109.7 |
C9—C10—H10A | 109.3 | H10C—C10'—H10D | 108.2 |
C11—C10—H10A | 109.3 | C12'—C11'—C10' | 110.5 (2) |
C9—C10—H10B | 109.3 | C12'—C11'—H11C | 109.6 |
C11—C10—H10B | 109.3 | C10'—C11'—H11C | 109.6 |
H10A—C10—H10B | 108.0 | C12'—C11'—H11D | 109.6 |
C12—C11—C10 | 113.9 (2) | C10'—C11'—H11D | 109.6 |
C12—C11—H11A | 108.8 | H11C—C11'—H11D | 108.1 |
C10—C11—H11A | 108.8 | C11'—C12'—C13' | 111.1 (2) |
C12—C11—H11B | 108.8 | C11'—C12'—H12C | 109.4 |
C10—C11—H11B | 108.8 | C13'—C12'—H12C | 109.4 |
H11A—C11—H11B | 107.7 | C11'—C12'—H12D | 109.4 |
C11—C12—C13 | 113.2 (3) | C13'—C12'—H12D | 109.4 |
C11—C12—H12A | 108.9 | H12C—C12'—H12D | 108.0 |
C13—C12—H12A | 108.9 | C14'—C13'—C12' | 110.3 (2) |
C11—C12—H12B | 108.9 | C14'—C13'—H13C | 109.6 |
C13—C12—H12B | 108.9 | C12'—C13'—H13C | 109.6 |
H12A—C12—H12B | 107.8 | C14'—C13'—H13D | 109.6 |
C12—C13—C14 | 110.4 (2) | C12'—C13'—H13D | 109.6 |
C12—C13—H13A | 109.6 | H13C—C13'—H13D | 108.1 |
C14—C13—H13A | 109.6 | C9'—C14'—C13' | 125.4 (2) |
C12—C13—H13B | 109.6 | C9'—C14'—S1' | 113.70 (17) |
C14—C13—H13B | 109.6 | C13'—C14'—S1' | 120.92 (18) |
H13A—C13—H13B | 108.1 | C20'—C15'—C16' | 121.16 (19) |
C9—C14—C13 | 125.7 (2) | C20'—C15'—N1' | 119.35 (18) |
C9—C14—S1 | 113.33 (18) | C16'—C15'—N1' | 119.45 (18) |
C13—C14—S1 | 120.97 (19) | C15'—C16'—C17' | 119.3 (2) |
C20—C15—C16 | 120.4 (2) | C15'—C16'—H16A | 120.3 |
C20—C15—N1 | 119.65 (19) | C17'—C16'—H16A | 120.3 |
C16—C15—N1 | 119.94 (19) | C18'—C17'—C16' | 119.0 (2) |
C15—C16—C17 | 119.6 (2) | C18'—C17'—H17A | 120.5 |
C15—C16—H16 | 120.2 | C16'—C17'—H17A | 120.5 |
C17—C16—H16 | 120.2 | C17'—C18'—C19' | 121.9 (2) |
C18—C17—C16 | 119.3 (2) | C17'—C18'—Cl1' | 119.74 (18) |
C18—C17—H17 | 120.4 | C19'—C18'—Cl1' | 118.33 (18) |
C16—C17—H17 | 120.4 | C18'—C19'—C20' | 119.1 (2) |
C19—C18—C17 | 121.4 (2) | C18'—C19'—H19A | 120.5 |
C19—C18—Cl1 | 119.1 (2) | C20'—C19'—H19A | 120.5 |
C17—C18—Cl1 | 119.5 (2) | C15'—C20'—C19' | 119.4 (2) |
C18—C19—C20 | 119.1 (2) | C15'—C20'—H20A | 120.3 |
C18—C19—H19 | 120.4 | C19'—C20'—H20A | 120.3 |
C20—C19—H19 | 120.4 | N3'—C21'—C22' | 105.8 (5) |
C15—C20—C19 | 120.1 (2) | N3'—C21'—H21C | 110.6 |
C15—C20—H20 | 119.9 | C22'—C21'—H21C | 110.6 |
C19—C20—H20 | 119.9 | N3'—C21'—H21D | 110.6 |
N3—C21—C22 | 112.82 (19) | C22'—C21'—H21D | 110.6 |
N3—C21—H21A | 109.0 | H21C—C21'—H21D | 108.7 |
C22—C21—H21A | 109.0 | C21'—C22'—C23' | 110.0 (5) |
N3—C21—H21B | 109.0 | C21'—C22'—H22C | 109.7 |
C22—C21—H21B | 109.0 | C23'—C22'—H22C | 109.7 |
H21A—C21—H21B | 107.8 | C21'—C22'—H22D | 109.7 |
C21—C22—C23 | 112.3 (2) | C23'—C22'—H22D | 109.7 |
C21—C22—H22A | 109.1 | H22C—C22'—H22D | 108.2 |
C23—C22—H22A | 109.1 | N3'—C21A—C22A | 112.9 (6) |
C21—C22—H22B | 109.1 | N3'—C21A—H21E | 109.0 |
C23—C22—H22B | 109.1 | C22A—C21A—H21E | 109.0 |
H22A—C22—H22B | 107.9 | N3'—C21A—H21F | 109.0 |
C22—C23—H23A | 109.5 | C22A—C21A—H21F | 109.0 |
C22—C23—H23B | 109.5 | H21E—C21A—H21F | 107.8 |
H23A—C23—H23B | 109.5 | C21A—C22A—C23A | 112.2 (6) |
C22—C23—H23C | 109.5 | C21A—C22A—H22E | 109.2 |
H23A—C23—H23C | 109.5 | C23A—C22A—H22E | 109.2 |
H23B—C23—H23C | 109.5 | C21A—C22A—H22F | 109.2 |
C7'—S1'—C14' | 91.06 (10) | C23A—C22A—H22F | 109.2 |
C1'—N1'—C2' | 122.54 (17) | H22E—C22A—H22F | 107.9 |
C1'—N1'—C15' | 120.77 (17) | C22A—C23A—H23G | 109.5 |
C2'—N1'—C15' | 116.59 (16) | C22A—C23A—H23H | 109.5 |
C1'—N2'—C4' | 117.71 (17) | H23G—C23A—H23H | 109.5 |
C1'—N3'—C21' | 125.3 (4) | C22A—C23A—H23I | 109.5 |
C1'—N3'—C21A | 116.9 (3) | H23G—C23A—H23I | 109.5 |
C1'—N3'—H3'A | 117.3 | H23H—C23A—H23I | 109.5 |
C21'—N3'—H3'A | 117.3 | ||
C4—N2—C1—N3 | 176.93 (18) | C21A—N3'—C1'—N2' | −5.5 (6) |
C4—N2—C1—N1 | −3.1 (3) | C21'—N3'—C1'—N1' | −164.6 (4) |
C21—N3—C1—N2 | 3.0 (3) | C21A—N3'—C1'—N1' | 173.6 (6) |
C21—N3—C1—N1 | −177.02 (17) | C2'—N1'—C1'—N2' | 1.6 (3) |
C2—N1—C1—N2 | −0.7 (3) | C15'—N1'—C1'—N2' | 177.81 (19) |
C15—N1—C1—N2 | −176.76 (18) | C2'—N1'—C1'—N3' | −177.4 (2) |
C2—N1—C1—N3 | 179.31 (18) | C15'—N1'—C1'—N3' | −1.2 (3) |
C15—N1—C1—N3 | 3.3 (3) | C1'—N1'—C2'—O1' | −180.0 (2) |
C1—N1—C2—O1 | −175.47 (18) | C15'—N1'—C2'—O1' | 3.7 (3) |
C15—N1—C2—O1 | 0.7 (3) | C1'—N1'—C2'—C3' | 0.2 (3) |
C1—N1—C2—C3 | 4.6 (3) | C15'—N1'—C2'—C3' | −176.12 (17) |
C15—N1—C2—C3 | −179.30 (16) | O1'—C2'—C3'—C4' | 177.3 (2) |
O1—C2—C3—C4 | 175.3 (2) | N1'—C2'—C3'—C4' | −3.0 (3) |
N1—C2—C3—C4 | −4.7 (3) | O1'—C2'—C3'—C5' | −3.4 (4) |
O1—C2—C3—C5 | −4.8 (3) | N1'—C2'—C3'—C5' | 176.36 (19) |
N1—C2—C3—C5 | 175.16 (18) | C1'—N2'—C4'—C3' | −2.7 (3) |
C1—N2—C4—C3 | 2.7 (3) | C1'—N2'—C4'—C8' | 178.67 (19) |
C1—N2—C4—C8 | −176.41 (17) | C5'—C3'—C4'—N2' | −174.88 (19) |
C5—C3—C4—N2 | −178.51 (18) | C2'—C3'—C4'—N2' | 4.5 (3) |
C2—C3—C4—N2 | 1.4 (3) | C5'—C3'—C4'—C8' | 3.7 (3) |
C5—C3—C4—C8 | 0.6 (3) | C2'—C3'—C4'—C8' | −176.92 (18) |
C2—C3—C4—C8 | −179.56 (17) | C7'—N4'—C5'—C3' | −2.8 (3) |
C7—N4—C5—C3 | −2.3 (3) | C7'—N4'—C5'—C6' | 178.8 (2) |
C7—N4—C5—C6 | 178.72 (19) | C4'—C3'—C5'—N4' | 0.6 (3) |
C4—C3—C5—N4 | 1.4 (3) | C2'—C3'—C5'—N4' | −178.7 (2) |
C2—C3—C5—N4 | −178.49 (19) | C4'—C3'—C5'—C6' | 178.8 (2) |
C4—C3—C5—C6 | −179.8 (2) | C2'—C3'—C5'—C6' | −0.5 (3) |
C2—C3—C5—C6 | 0.4 (3) | C5'—N4'—C7'—C8' | 0.7 (3) |
C5—N4—C7—C8 | 1.5 (3) | C5'—N4'—C7'—S1' | −179.56 (17) |
C5—N4—C7—S1 | −179.10 (16) | C14'—S1'—C7'—N4' | 179.32 (19) |
C14—S1—C7—N4 | −179.7 (2) | C14'—S1'—C7'—C8' | −0.88 (18) |
C14—S1—C7—C8 | −0.19 (18) | N4'—C7'—C8'—C4' | 3.6 (3) |
N4—C7—C8—C4 | 0.4 (3) | S1'—C7'—C8'—C4' | −176.18 (15) |
S1—C7—C8—C4 | −179.06 (14) | N4'—C7'—C8'—C9' | −177.6 (2) |
N4—C7—C8—C9 | 179.4 (2) | S1'—C7'—C8'—C9' | 2.6 (2) |
S1—C7—C8—C9 | 0.0 (2) | N2'—C4'—C8'—C7' | 173.20 (18) |
N2—C4—C8—C7 | 177.77 (18) | C3'—C4'—C8'—C7' | −5.5 (3) |
C3—C4—C8—C7 | −1.4 (3) | N2'—C4'—C8'—C9' | −5.4 (3) |
N2—C4—C8—C9 | −1.0 (3) | C3'—C4'—C8'—C9' | 176.0 (2) |
C3—C4—C8—C9 | 179.8 (2) | C7'—C8'—C9'—C14' | −3.5 (3) |
C7—C8—C9—C14 | 0.3 (3) | C4'—C8'—C9'—C14' | 175.1 (2) |
C4—C8—C9—C14 | 179.1 (2) | C7'—C8'—C9'—C10' | 172.5 (2) |
C7—C8—C9—C10 | 179.5 (2) | C4'—C8'—C9'—C10' | −8.9 (4) |
C4—C8—C9—C10 | −1.6 (4) | C14'—C9'—C10'—C11' | 14.9 (3) |
C14—C9—C10—C11 | −12.4 (3) | C8'—C9'—C10'—C11' | −160.7 (2) |
C8—C9—C10—C11 | 168.5 (2) | C9'—C10'—C11'—C12' | −49.8 (3) |
C9—C10—C11—C12 | 41.3 (3) | C10'—C11'—C12'—C13' | 65.6 (3) |
C10—C11—C12—C13 | −58.9 (4) | C11'—C12'—C13'—C14' | −41.8 (3) |
C11—C12—C13—C14 | 42.8 (4) | C8'—C9'—C14'—C13' | −176.7 (2) |
C8—C9—C14—C13 | 178.7 (2) | C10'—C9'—C14'—C13' | 7.0 (4) |
C10—C9—C14—C13 | −0.6 (4) | C8'—C9'—C14'—S1' | 2.8 (2) |
C8—C9—C14—S1 | −0.4 (3) | C10'—C9'—C14'—S1' | −173.43 (17) |
C10—C9—C14—S1 | −179.73 (17) | C12'—C13'—C14'—C9' | 6.6 (3) |
C12—C13—C14—C9 | −14.4 (4) | C12'—C13'—C14'—S1' | −172.92 (18) |
C12—C13—C14—S1 | 164.7 (2) | C7'—S1'—C14'—C9' | −1.19 (19) |
C7—S1—C14—C9 | 0.4 (2) | C7'—S1'—C14'—C13' | 178.4 (2) |
C7—S1—C14—C13 | −178.8 (2) | C1'—N1'—C15'—C20' | −78.1 (3) |
C1—N1—C15—C20 | 73.4 (3) | C2'—N1'—C15'—C20' | 98.3 (2) |
C2—N1—C15—C20 | −102.8 (2) | C1'—N1'—C15'—C16' | 104.0 (2) |
C1—N1—C15—C16 | −105.8 (2) | C2'—N1'—C15'—C16' | −79.5 (2) |
C2—N1—C15—C16 | 78.0 (3) | C20'—C15'—C16'—C17' | −1.9 (3) |
C20—C15—C16—C17 | −1.8 (3) | N1'—C15'—C16'—C17' | 175.91 (19) |
N1—C15—C16—C17 | 177.4 (2) | C15'—C16'—C17'—C18' | 0.9 (3) |
C15—C16—C17—C18 | 0.3 (4) | C16'—C17'—C18'—C19' | 1.1 (3) |
C16—C17—C18—C19 | 1.0 (4) | C16'—C17'—C18'—Cl1' | −178.44 (17) |
C16—C17—C18—Cl1 | −178.53 (18) | C17'—C18'—C19'—C20' | −2.1 (3) |
C17—C18—C19—C20 | −0.7 (4) | Cl1'—C18'—C19'—C20' | 177.41 (16) |
Cl1—C18—C19—C20 | 178.84 (18) | C16'—C15'—C20'—C19' | 0.9 (3) |
C16—C15—C20—C19 | 2.1 (3) | N1'—C15'—C20'—C19' | −176.94 (18) |
N1—C15—C20—C19 | −177.1 (2) | C18'—C19'—C20'—C15' | 1.1 (3) |
C18—C19—C20—C15 | −0.9 (4) | C1'—N3'—C21'—C22' | −98.1 (7) |
C1—N3—C21—C22 | 82.8 (3) | C21A—N3'—C21'—C22' | −26.3 (15) |
N3—C21—C22—C23 | −178.0 (2) | N3'—C21'—C22'—C23' | −174.9 (6) |
C4'—N2'—C1'—N3' | 178.58 (19) | C1'—N3'—C21A—C22A | −166.4 (7) |
C4'—N2'—C1'—N1' | −0.4 (3) | C21'—N3'—C21A—C22A | 73.9 (16) |
C21'—N3'—C1'—N2' | 16.4 (5) | N3'—C21A—C22A—C23A | −171.7 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3′—H3′B···N4i | 0.90 | 2.30 | 3.072 (3) | 144 |
N3—H3···O1′ii | 0.86 | 2.22 | 2.912 (2) | 138 |
C13′—H13C···O1iii | 0.97 | 2.38 | 3.285 (3) | 154 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y, z−1; (iii) −x+1, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C23H23ClN4OS |
Mr | 438.96 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 292 |
a, b, c (Å) | 11.8884 (6), 13.3784 (7), 15.7892 (8) |
α, β, γ (°) | 114.054 (1), 98.926 (1), 101.335 (1) |
V (Å3) | 2169.42 (19) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.30 |
Crystal size (mm) | 0.40 × 0.30 × 0.30 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.891, 0.917 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 25134, 9849, 6468 |
Rint | 0.040 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.156, 1.03 |
No. of reflections | 9849 |
No. of parameters | 574 |
No. of restraints | 7 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.32, −0.21 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.
S1—C7 | 1.737 (2) | S1'—C7' | 1.734 (2) |
S1—C14 | 1.738 (3) | S1'—C14' | 1.735 (3) |
O1—C2 | 1.209 (2) | O1'—C2' | 1.220 (2) |
N2—C1 | 1.308 (2) | N2'—C1' | 1.307 (2) |
N2—C4 | 1.367 (3) | N2'—C4' | 1.369 (3) |
N4—C5 | 1.334 (3) | N4'—C5' | 1.327 (3) |
N4—C7 | 1.349 (3) | N4'—C7' | 1.343 (3) |
C7—S1—C14 | 91.00 (11) | C7'—S1'—C14' | 91.06 (10) |
C1—N2—C4 | 118.07 (18) | C1'—N2'—C4' | 117.71 (17) |
C5—N4—C7 | 116.82 (18) | C5'—N4'—C7' | 116.56 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3'—H3'B···N4i | 0.90 | 2.30 | 3.072 (3) | 144 |
N3—H3···O1'ii | 0.86 | 2.22 | 2.912 (2) | 138 |
C13'—H13C···O1iii | 0.97 | 2.38 | 3.285 (3) | 154 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y, z−1; (iii) −x+1, −y, −z. |
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Many pyridopyrimidines exhibit pharmaceutical and germicidal activities (Anderson & Broom, 1977). Over two hundred tetrahydro- and octahydropyrido[4,3-d]pyrimidines have been synthesized as potential diuretic, antirheumatic and bacteriostatic drugs, but only a few of fully aromatic pyrido[4,3-d]pyrimidines are known. An important synthetic route of pyrido[4,3-d]pyrimidine is the condensation reaction of 4-aminonicotinic acid and amines (Ismail & Wibberley, 1967). However, this method often requires long reaction times. Recently, we have developed a new and facile regioselective annulation process, which proceeded smoothly under mild conditions via a tandem aza-Wittig and cyclization reaction, to synthesize novel pyridopyrimidine derivatives (Zhou et al., 2005). In this paper, we report the structure of the title compound, (I).
The asymmetric unit contains two crystallographically independent molecules in which the orientations of the propylamine group and chlorophenyl rings with respect to the fused ring system are different (Fig. 1). The bond lengths and angles in the thieno[2,3-b]pyridine ring system (Table 1) are in agreement with the corresponding values observed in a similar compound (Patel et al., 2003). The C—S bond lengths are longer than the values observed in both free thiophene (1.714 Å; Bonham,Momany, 1963), measured using electron diffraction, and thieno[2,3-c]pyridine [1.728 (1) and 1.731 (1) Å; Nerenz et al., 1997]. The C7—S1—C14 angle is narrower than that observed in free thiophene [92.2 (2)°]. The C5—N4—C7 angles are smaller than 120° (Ghosh & Simonsen, 1993). The C═N bond lengths (Table 1) are longer than the typical C═N distance of 1.28 Å (Zhao et al., 2005). In both independent molecules, the central aromatic ring system consisting of thiophene, pyridine and pyrimidine rings is essentially planar, and the terminal cyclohexene ring adopts a half-chair conformation. The crystal packing is stabilized by N—H···O, N—H···N and C—H···O hydrogen bonds (Table 2). The C15'—C20' ring and the N4/C3—C5/C7—C8 ring of the inversion related molecule at (1 − x, 1 − y, 1 − z) are stacked with a centroid–centroid distance of 3.754 (1) Å, indicating a weak π–π stacking interaction.