The title compound, C
48H
44N
6O
2S·2C
2H
3N, was synthesized by the intermolecular [3+2]-cycloaddition of an azomethine ylide, derived from isatin and sarcosine by a decarboxylative route, and 7-benzyl-9-benzylidene-2-[4-(dimethylamino)benzylidene]-5-phenyl-2,3,6,7,8,9-hexahydro-5
H-pyrido[4,3-
d]thiazolo[3,2-
a]pyrimidin-3-one. In the molecule, the two spiro junctions link a planar 2-oxindole system, a pyrrolidine ring in an envelope conformation and a thiazolidone ring of the fused pyrimidine ring system. The packing of the molecules in the crystal structure is mainly stabilized by N—H
O hydrogen bonds.
Supporting information
CCDC reference: 274639
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.005 Å
- Disorder in main residue
- R factor = 0.053
- wR factor = 0.157
- Data-to-parameter ratio = 12.7
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.92 Ratio
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.80 Ratio
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT202_ALERT_3_C Isotropic non-H Atoms in Anion/Solvent ......... 3
PLAT220_ALERT_2_C Large Non-Solvent N Ueq(max)/Ueq(min) ... 3.18 Ratio
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C4'
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C6'
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C25
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C4
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C2'
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C21
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C42
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C2
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C51
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C49
PLAT301_ALERT_3_C Main Residue Disorder ......................... 21.00 Perc.
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 33.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 5
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 16.00 Deg.
C2' -C1 -C2 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 0.00 Deg.
H1A -C1 -H1C 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 0.00 Deg.
H1B -C1 -H1D 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 5.10 Deg.
C41' -C40 -C41 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 2.60 Deg.
H40A -C40 -H40B 1.555 1.555 1.555
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
23 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
15 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
5 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
7"-Benzyl-9"-benzylidene-4'-[4-(dimethylamino)phenyl]-1'-methyl-5"-phenyl-
2",3",6",7",8",9"-hexahydro-1
H-indole-3(2
H)-spiro-2'-pyrrolidine-3'-spiro-2''-
pyrido[4,3-
d]thiazolo[3,2-
a]pyrimidine-2,2''-dione acetonitrile
disolvate
top
Crystal data top
C48H44N6O2S·2C2H3N | F(000) = 900 |
Mr = 851.06 | Dx = 1.218 Mg m−3 |
Triclinic, P1 | Melting point: 201 K |
a = 12.4130 (14) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.1265 (15) Å | Cell parameters from 3369 reflections |
c = 15.1590 (18) Å | θ = 2.3–24.0° |
α = 87.559 (2)° | µ = 0.12 mm−1 |
β = 74.392 (2)° | T = 294 K |
γ = 77.313 (2)° | Block, colorless |
V = 2320.5 (5) Å3 | 0.26 × 0.22 × 0.20 mm |
Z = 2 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 8127 independent reflections |
Radiation source: fine-focus sealed tube | 5109 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
φ and ω scans | θmax = 25.0°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Bruker,1997) | h = −14→13 |
Tmin = 0.960, Tmax = 0.972 | k = −13→15 |
11894 measured reflections | l = −18→17 |
Refinement top
Refinement on F2 | 66 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.053 | w = 1/[σ2(Fo2) + (0.0629P)2 + 1.1607P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.157 | (Δ/σ)max = 0.003 |
S = 1.03 | Δρmax = 0.43 e Å−3 |
8127 reflections | Δρmin = −0.32 e Å−3 |
642 parameters | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
S1 | 0.38776 (6) | 0.82850 (6) | 0.23151 (5) | 0.0438 (2) | |
O1 | 0.13443 (17) | 0.71519 (16) | 0.20890 (13) | 0.0500 (5) | |
O2 | 0.50109 (18) | 0.86219 (16) | 0.03387 (15) | 0.0547 (6) | |
N1 | −0.0030 (2) | 0.86532 (18) | 0.63964 (15) | 0.0424 (6) | |
N2 | 0.28405 (19) | 0.85995 (18) | 0.40903 (15) | 0.0409 (6) | |
N3 | 0.19263 (18) | 0.78586 (17) | 0.31729 (14) | 0.0362 (5) | |
N4 | 0.3478 (2) | 0.9972 (2) | 0.03568 (18) | 0.0487 (7) | |
H4 | 0.384 (3) | 1.044 (3) | 0.020 (2) | 0.061 (10)* | |
N5 | 0.3155 (2) | 0.75362 (19) | 0.00839 (15) | 0.0465 (6) | |
C1 | −0.1177 (3) | 0.9007 (2) | 0.7011 (2) | 0.0528 (8) | |
H1A | −0.1666 | 0.9430 | 0.6680 | 0.063* | 0.48 (3) |
H1B | −0.1135 | 0.9424 | 0.7500 | 0.063* | 0.48 (3) |
H1C | −0.1666 | 0.9430 | 0.6680 | 0.063* | 0.52 (3) |
H1D | −0.1135 | 0.9424 | 0.7500 | 0.063* | 0.52 (3) |
C2 | −0.1689 (8) | 0.8046 (6) | 0.7413 (3) | 0.046 (3) | 0.48 (3) |
C3 | −0.1092 (14) | 0.7232 (6) | 0.7828 (3) | 0.070 (3) | 0.48 (3) |
H3A | −0.0334 | 0.7210 | 0.7816 | 0.084* | 0.48 (3) |
C4 | −0.163 (2) | 0.6450 (8) | 0.8260 (3) | 0.103 (5) | 0.48 (3) |
H4A | −0.1227 | 0.5905 | 0.8538 | 0.124* | 0.48 (3) |
C5 | −0.2759 (19) | 0.6482 (11) | 0.8278 (6) | 0.099 (6) | 0.48 (3) |
H5A | −0.3117 | 0.5959 | 0.8567 | 0.119* | 0.48 (3) |
C6 | −0.3356 (12) | 0.7296 (12) | 0.7863 (10) | 0.106 (7) | 0.48 (3) |
H6A | −0.4114 | 0.7318 | 0.7875 | 0.127* | 0.48 (3) |
C7 | −0.2821 (7) | 0.8078 (9) | 0.7430 (9) | 0.084 (4) | 0.48 (3) |
H7A | −0.3221 | 0.8622 | 0.7153 | 0.101* | 0.48 (3) |
C2' | −0.1918 (6) | 0.8253 (6) | 0.7282 (5) | 0.049 (3) | 0.52 (3) |
C3' | −0.1547 (13) | 0.7442 (6) | 0.7823 (2) | 0.066 (3) | 0.52 (3) |
H3'A | −0.0834 | 0.7365 | 0.7937 | 0.079* | 0.52 (3) |
C4' | −0.2241 (18) | 0.6746 (9) | 0.8192 (4) | 0.102 (6) | 0.52 (3) |
H4'A | −0.1992 | 0.6203 | 0.8554 | 0.122* | 0.52 (3) |
C5' | −0.3306 (15) | 0.6861 (12) | 0.8021 (9) | 0.100 (7) | 0.52 (3) |
H5'A | −0.3770 | 0.6396 | 0.8268 | 0.120* | 0.52 (3) |
C6' | −0.3677 (8) | 0.7673 (12) | 0.7480 (13) | 0.119 (6) | 0.52 (3) |
H6'A | −0.4390 | 0.7750 | 0.7365 | 0.143* | 0.52 (3) |
C7' | −0.2984 (4) | 0.8369 (9) | 0.7110 (10) | 0.089 (4) | 0.52 (3) |
H7'A | −0.3232 | 0.8911 | 0.6748 | 0.106* | 0.52 (3) |
C8 | 0.0569 (2) | 0.9513 (2) | 0.62858 (19) | 0.0457 (7) | |
H8A | 0.0630 | 0.9699 | 0.6880 | 0.055* | |
H8B | 0.0116 | 1.0116 | 0.6063 | 0.055* | |
C9 | 0.1744 (2) | 0.9263 (2) | 0.56401 (19) | 0.0412 (7) | |
C10 | 0.2659 (3) | 0.9553 (2) | 0.5769 (2) | 0.0511 (8) | |
H10 | 0.3339 | 0.9353 | 0.5312 | 0.061* | |
C11 | 0.2718 (3) | 1.0151 (3) | 0.6551 (2) | 0.0560 (9) | |
C12 | 0.3648 (4) | 0.9837 (3) | 0.6919 (3) | 0.0810 (12) | |
H12 | 0.4218 | 0.9259 | 0.6668 | 0.097* | |
C13 | 0.3736 (5) | 1.0375 (4) | 0.7657 (3) | 0.1026 (16) | |
H13 | 0.4355 | 1.0142 | 0.7904 | 0.123* | |
C14 | 0.2935 (6) | 1.1234 (5) | 0.8022 (3) | 0.1029 (18) | |
H14 | 0.3008 | 1.1598 | 0.8509 | 0.123* | |
C15 | 0.2015 (4) | 1.1563 (4) | 0.7666 (3) | 0.0948 (16) | |
H15 | 0.1456 | 1.2149 | 0.7916 | 0.114* | |
C16 | 0.1911 (3) | 1.1026 (3) | 0.6934 (3) | 0.0720 (11) | |
H16 | 0.1284 | 1.1261 | 0.6698 | 0.086* | |
C17 | 0.1830 (2) | 0.8650 (2) | 0.48234 (18) | 0.0387 (7) | |
C18 | 0.0972 (2) | 0.8204 (2) | 0.47770 (18) | 0.0375 (6) | |
C19 | −0.0113 (2) | 0.8299 (2) | 0.55252 (18) | 0.0436 (7) | |
H19A | −0.0721 | 0.8786 | 0.5341 | 0.052* | |
H19B | −0.0322 | 0.7624 | 0.5607 | 0.052* | |
C20 | 0.1052 (2) | 0.7558 (2) | 0.39540 (17) | 0.0377 (6) | |
H20 | 0.0311 | 0.7730 | 0.3808 | 0.045* | |
C21 | 0.1350 (3) | 0.6392 (2) | 0.41054 (19) | 0.0448 (7) | |
C22 | 0.2232 (3) | 0.5971 (3) | 0.4473 (3) | 0.0768 (11) | |
H22 | 0.2635 | 0.6403 | 0.4658 | 0.092* | |
C23 | 0.2532 (4) | 0.4899 (4) | 0.4574 (4) | 0.1048 (16) | |
H23 | 0.3150 | 0.4618 | 0.4810 | 0.126* | |
C24 | 0.1938 (6) | 0.4257 (3) | 0.4332 (4) | 0.1053 (18) | |
H24 | 0.2130 | 0.3541 | 0.4416 | 0.126* | |
C25 | 0.1067 (6) | 0.4673 (4) | 0.3969 (3) | 0.1092 (18) | |
H25 | 0.0662 | 0.4236 | 0.3795 | 0.131* | |
C26 | 0.0761 (4) | 0.5738 (3) | 0.3849 (3) | 0.0766 (11) | |
H26 | 0.0156 | 0.6010 | 0.3595 | 0.092* | |
C27 | 0.2807 (2) | 0.8256 (2) | 0.33255 (18) | 0.0367 (6) | |
C28 | 0.2046 (2) | 0.7543 (2) | 0.22955 (18) | 0.0381 (6) | |
C29 | 0.3177 (2) | 0.7670 (2) | 0.16336 (18) | 0.0383 (6) | |
C30 | 0.3019 (2) | 0.8337 (2) | 0.07756 (18) | 0.0395 (7) | |
C31 | 0.1953 (2) | 0.9195 (2) | 0.08594 (18) | 0.0402 (7) | |
C32 | 0.0799 (3) | 0.9173 (3) | 0.10955 (19) | 0.0486 (8) | |
H32 | 0.0562 | 0.8551 | 0.1260 | 0.058* | |
C33 | 0.0002 (3) | 1.0099 (3) | 0.1083 (2) | 0.0557 (8) | |
H33 | −0.0776 | 1.0102 | 0.1262 | 0.067* | |
C34 | 0.0359 (3) | 1.1012 (3) | 0.0807 (2) | 0.0597 (9) | |
H34 | −0.0186 | 1.1621 | 0.0796 | 0.072* | |
C35 | 0.1506 (3) | 1.1043 (3) | 0.0546 (2) | 0.0544 (8) | |
H35 | 0.1745 | 1.1657 | 0.0350 | 0.065* | |
C36 | 0.2280 (2) | 1.0128 (2) | 0.05867 (19) | 0.0436 (7) | |
C37 | 0.3977 (3) | 0.8980 (2) | 0.04736 (19) | 0.0435 (7) | |
C38 | 0.3255 (3) | 0.7907 (3) | −0.0852 (2) | 0.0652 (10) | |
H38A | 0.2598 | 0.8447 | −0.0864 | 0.098* | |
H38B | 0.3297 | 0.7337 | −0.1246 | 0.098* | |
H38C | 0.3936 | 0.8179 | −0.1061 | 0.098* | |
C39 | 0.4091 (3) | 0.6689 (2) | 0.0188 (2) | 0.0525 (8) | |
H39A | 0.4825 | 0.6880 | −0.0054 | 0.063* | |
H39B | 0.4093 | 0.6058 | −0.0123 | 0.063* | |
C40 | 0.3840 (2) | 0.6538 (2) | 0.12194 (19) | 0.0455 (7) | |
H40A | 0.3273 | 0.6119 | 0.1362 | 0.055* | 0.52 (3) |
H40B | 0.3296 | 0.6097 | 0.1375 | 0.055* | 0.48 (3) |
C41 | 0.4801 (7) | 0.5954 (12) | 0.1621 (9) | 0.059 (6) | 0.52 (3) |
C42 | 0.5882 (8) | 0.6182 (13) | 0.1335 (10) | 0.054 (5) | 0.52 (3) |
H42A | 0.6025 | 0.6682 | 0.0891 | 0.065* | 0.52 (3) |
C43 | 0.6751 (8) | 0.5662 (16) | 0.1713 (14) | 0.083 (7) | 0.52 (3) |
H43A | 0.7474 | 0.5815 | 0.1522 | 0.099* | 0.52 (3) |
C44 | 0.6538 (12) | 0.4915 (14) | 0.2377 (15) | 0.084 (7) | 0.52 (3) |
C45 | 0.5456 (14) | 0.4686 (11) | 0.2663 (12) | 0.091 (6) | 0.52 (3) |
H45A | 0.5314 | 0.4186 | 0.3107 | 0.109* | 0.52 (3) |
C46 | 0.4588 (10) | 0.5206 (12) | 0.2285 (11) | 0.081 (7) | 0.52 (3) |
H46A | 0.3864 | 0.5053 | 0.2476 | 0.097* | 0.52 (3) |
N6 | 0.7493 (14) | 0.4540 (16) | 0.2774 (17) | 0.108 (6) | 0.52 (3) |
C47 | 0.8560 (14) | 0.492 (2) | 0.2421 (19) | 0.144 (4) | 0.52 (3) |
H47A | 0.8949 | 0.4622 | 0.1821 | 0.216* | 0.52 (3) |
H47B | 0.9045 | 0.4708 | 0.2824 | 0.216* | 0.52 (3) |
H47C | 0.8381 | 0.5664 | 0.2388 | 0.216* | 0.52 (3) |
C48 | 0.765 (2) | 0.3442 (14) | 0.3054 (19) | 0.135 (4) | 0.52 (3) |
H48A | 0.7009 | 0.3354 | 0.3545 | 0.202* | 0.52 (3) |
H48B | 0.8340 | 0.3251 | 0.3255 | 0.202* | 0.52 (3) |
H48C | 0.7718 | 0.3004 | 0.2543 | 0.202* | 0.52 (3) |
C41' | 0.4856 (8) | 0.6025 (11) | 0.1575 (10) | 0.047 (6) | 0.48 (3) |
C42' | 0.5909 (8) | 0.6311 (13) | 0.1294 (11) | 0.073 (7) | 0.48 (3) |
H42B | 0.6007 | 0.6848 | 0.0880 | 0.088* | 0.48 (3) |
C43' | 0.6814 (9) | 0.5794 (15) | 0.1633 (15) | 0.073 (6) | 0.48 (3) |
H43B | 0.7518 | 0.5985 | 0.1445 | 0.087* | 0.48 (3) |
C44' | 0.6666 (12) | 0.4991 (13) | 0.2252 (16) | 0.085 (7) | 0.48 (3) |
C45' | 0.5614 (14) | 0.4706 (10) | 0.2532 (12) | 0.073 (6) | 0.48 (3) |
H45B | 0.5515 | 0.4169 | 0.2946 | 0.087* | 0.48 (3) |
C46' | 0.4708 (10) | 0.5223 (11) | 0.2194 (10) | 0.053 (5) | 0.48 (3) |
H46B | 0.4004 | 0.5031 | 0.2381 | 0.064* | 0.48 (3) |
N6' | 0.7550 (18) | 0.4267 (17) | 0.2554 (17) | 0.115 (7) | 0.48 (3) |
C47' | 0.8485 (17) | 0.472 (2) | 0.270 (2) | 0.144 (4) | 0.48 (3) |
H47D | 0.8160 | 0.5316 | 0.3112 | 0.216* | 0.48 (3) |
H47E | 0.8913 | 0.4943 | 0.2125 | 0.216* | 0.48 (3) |
H47F | 0.8985 | 0.4210 | 0.2961 | 0.216* | 0.48 (3) |
C48' | 0.720 (2) | 0.3476 (17) | 0.3231 (17) | 0.135 (4) | 0.48 (3) |
H48D | 0.6980 | 0.2951 | 0.2941 | 0.202* | 0.48 (3) |
H48E | 0.6572 | 0.3806 | 0.3722 | 0.202* | 0.48 (3) |
H48F | 0.7838 | 0.3157 | 0.3472 | 0.202* | 0.48 (3) |
N7 | 1.0779 (4) | 0.3506 (4) | 0.9666 (5) | 0.155 (2) | |
C49 | 0.9842 (5) | 0.3741 (3) | 0.9734 (3) | 0.0864 (13) | |
C50 | 0.8635 (4) | 0.4052 (4) | 0.9821 (4) | 0.127 (2) | |
H50A | 0.8264 | 0.4441 | 1.0384 | 0.190* | |
H50B | 0.8326 | 0.3443 | 0.9823 | 0.190* | |
H50C | 0.8508 | 0.4481 | 0.9314 | 0.190* | |
N8 | 0.4299 (17) | 0.2150 (15) | 0.4534 (12) | 0.228 (9)* | 0.470 (13) |
C51 | 0.4315 (15) | 0.2384 (12) | 0.5238 (11) | 0.146 (6)* | 0.470 (13) |
C52 | 0.4488 (14) | 0.3056 (13) | 0.5951 (11) | 0.152 (6)* | 0.470 (13) |
H52A | 0.4806 | 0.3626 | 0.5658 | 0.228* | 0.470 (13) |
H52B | 0.5003 | 0.2643 | 0.6267 | 0.228* | 0.470 (13) |
H52C | 0.3765 | 0.3324 | 0.6381 | 0.228* | 0.470 (13) |
N8' | 0.5004 (11) | 0.2690 (10) | 0.4335 (6) | 0.174 (6)* | 0.530 (13) |
C51' | 0.4772 (10) | 0.2783 (10) | 0.5106 (6) | 0.115 (4)* | 0.530 (13) |
C52' | 0.4250 (8) | 0.2585 (8) | 0.6089 (5) | 0.085 (3)* | 0.530 (13) |
H52D | 0.3435 | 0.2678 | 0.6195 | 0.128* | 0.530 (13) |
H52E | 0.4411 | 0.3067 | 0.6469 | 0.128* | 0.530 (13) |
H52F | 0.4566 | 0.1883 | 0.6233 | 0.128* | 0.530 (13) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0408 (4) | 0.0531 (5) | 0.0382 (4) | −0.0189 (3) | −0.0038 (3) | −0.0045 (3) |
O1 | 0.0551 (13) | 0.0666 (14) | 0.0369 (11) | −0.0328 (11) | −0.0106 (10) | 0.0003 (10) |
O2 | 0.0431 (13) | 0.0556 (13) | 0.0587 (14) | −0.0145 (11) | −0.0004 (10) | 0.0081 (10) |
N1 | 0.0487 (14) | 0.0432 (14) | 0.0314 (13) | −0.0123 (11) | −0.0014 (11) | −0.0056 (10) |
N2 | 0.0370 (13) | 0.0487 (14) | 0.0369 (13) | −0.0105 (11) | −0.0077 (10) | −0.0059 (11) |
N3 | 0.0387 (13) | 0.0414 (13) | 0.0296 (12) | −0.0137 (10) | −0.0064 (10) | −0.0019 (10) |
N4 | 0.0478 (16) | 0.0444 (16) | 0.0511 (16) | −0.0175 (14) | −0.0031 (12) | 0.0068 (12) |
N5 | 0.0556 (16) | 0.0479 (15) | 0.0319 (13) | −0.0085 (12) | −0.0061 (11) | −0.0054 (11) |
C1 | 0.0520 (19) | 0.057 (2) | 0.0385 (17) | −0.0079 (16) | 0.0040 (14) | −0.0104 (14) |
C2 | 0.043 (5) | 0.064 (6) | 0.024 (5) | −0.009 (4) | 0.000 (4) | −0.008 (4) |
C3 | 0.078 (7) | 0.055 (5) | 0.083 (7) | −0.027 (5) | −0.020 (5) | 0.005 (5) |
C4 | 0.157 (13) | 0.073 (7) | 0.081 (8) | −0.044 (8) | −0.018 (7) | 0.006 (6) |
C5 | 0.084 (11) | 0.098 (10) | 0.105 (9) | −0.052 (9) | 0.021 (8) | −0.011 (7) |
C6 | 0.045 (7) | 0.082 (10) | 0.177 (14) | −0.036 (6) | 0.014 (8) | −0.015 (10) |
C7 | 0.038 (6) | 0.100 (8) | 0.109 (8) | −0.009 (5) | −0.014 (6) | −0.023 (7) |
C2' | 0.044 (5) | 0.050 (5) | 0.043 (4) | 0.001 (4) | −0.003 (4) | −0.014 (4) |
C3' | 0.081 (7) | 0.069 (6) | 0.051 (6) | −0.022 (6) | −0.016 (4) | 0.003 (4) |
C4' | 0.143 (15) | 0.074 (8) | 0.087 (8) | −0.056 (10) | −0.003 (8) | 0.004 (6) |
C5' | 0.111 (11) | 0.071 (9) | 0.097 (9) | −0.047 (10) | 0.033 (9) | −0.031 (7) |
C6' | 0.063 (7) | 0.156 (12) | 0.129 (12) | −0.034 (8) | 0.007 (7) | −0.042 (9) |
C7' | 0.055 (6) | 0.110 (8) | 0.093 (7) | −0.008 (5) | −0.011 (5) | −0.024 (6) |
C8 | 0.0551 (19) | 0.0436 (17) | 0.0363 (16) | −0.0109 (15) | −0.0072 (14) | −0.0066 (13) |
C9 | 0.0461 (17) | 0.0400 (16) | 0.0369 (16) | −0.0084 (13) | −0.0101 (13) | −0.0033 (13) |
C10 | 0.0492 (19) | 0.057 (2) | 0.0468 (18) | −0.0129 (15) | −0.0101 (14) | −0.0113 (15) |
C11 | 0.060 (2) | 0.065 (2) | 0.0491 (19) | −0.0264 (18) | −0.0129 (16) | −0.0089 (16) |
C12 | 0.093 (3) | 0.085 (3) | 0.085 (3) | −0.028 (2) | −0.047 (2) | −0.010 (2) |
C13 | 0.146 (5) | 0.114 (4) | 0.089 (3) | −0.066 (4) | −0.069 (3) | 0.008 (3) |
C14 | 0.148 (5) | 0.127 (4) | 0.058 (3) | −0.090 (4) | −0.015 (3) | −0.017 (3) |
C15 | 0.095 (3) | 0.099 (3) | 0.086 (3) | −0.052 (3) | 0.015 (3) | −0.047 (3) |
C16 | 0.067 (2) | 0.076 (3) | 0.074 (3) | −0.023 (2) | −0.0089 (19) | −0.028 (2) |
C17 | 0.0400 (16) | 0.0405 (16) | 0.0324 (15) | −0.0061 (13) | −0.0061 (12) | −0.0019 (12) |
C18 | 0.0410 (16) | 0.0370 (15) | 0.0320 (14) | −0.0077 (13) | −0.0058 (12) | −0.0015 (12) |
C19 | 0.0468 (17) | 0.0471 (17) | 0.0350 (16) | −0.0135 (14) | −0.0044 (13) | −0.0040 (13) |
C20 | 0.0363 (15) | 0.0446 (16) | 0.0309 (14) | −0.0127 (13) | −0.0029 (12) | −0.0026 (12) |
C21 | 0.0555 (19) | 0.0391 (16) | 0.0339 (15) | −0.0132 (15) | 0.0009 (14) | −0.0036 (13) |
C22 | 0.081 (3) | 0.056 (2) | 0.098 (3) | −0.015 (2) | −0.033 (2) | 0.018 (2) |
C23 | 0.108 (4) | 0.065 (3) | 0.125 (4) | 0.005 (3) | −0.027 (3) | 0.028 (3) |
C24 | 0.165 (5) | 0.041 (2) | 0.083 (3) | −0.010 (3) | 0.004 (3) | 0.000 (2) |
C25 | 0.193 (6) | 0.059 (3) | 0.087 (3) | −0.059 (3) | −0.030 (4) | −0.001 (2) |
C26 | 0.116 (3) | 0.057 (2) | 0.070 (2) | −0.041 (2) | −0.030 (2) | 0.0034 (19) |
C27 | 0.0353 (15) | 0.0366 (15) | 0.0377 (16) | −0.0080 (12) | −0.0085 (12) | −0.0012 (12) |
C28 | 0.0430 (16) | 0.0401 (16) | 0.0323 (15) | −0.0139 (13) | −0.0080 (12) | 0.0008 (12) |
C29 | 0.0421 (16) | 0.0415 (16) | 0.0325 (15) | −0.0156 (13) | −0.0063 (12) | −0.0002 (12) |
C30 | 0.0432 (16) | 0.0416 (16) | 0.0317 (15) | −0.0135 (13) | −0.0030 (12) | −0.0015 (12) |
C31 | 0.0444 (17) | 0.0460 (17) | 0.0284 (14) | −0.0102 (14) | −0.0057 (12) | −0.0028 (12) |
C32 | 0.0509 (19) | 0.057 (2) | 0.0396 (17) | −0.0174 (16) | −0.0097 (14) | −0.0011 (14) |
C33 | 0.0463 (19) | 0.070 (2) | 0.0498 (19) | −0.0085 (17) | −0.0146 (15) | −0.0007 (17) |
C34 | 0.056 (2) | 0.061 (2) | 0.056 (2) | 0.0020 (17) | −0.0155 (16) | −0.0023 (17) |
C35 | 0.066 (2) | 0.0489 (19) | 0.0437 (18) | −0.0078 (17) | −0.0097 (16) | 0.0006 (15) |
C36 | 0.0463 (18) | 0.0462 (18) | 0.0343 (16) | −0.0091 (14) | −0.0044 (13) | −0.0023 (13) |
C37 | 0.0451 (18) | 0.0465 (19) | 0.0345 (16) | −0.0137 (15) | −0.0003 (13) | 0.0008 (13) |
C38 | 0.083 (3) | 0.072 (2) | 0.0348 (17) | −0.0106 (19) | −0.0094 (17) | −0.0052 (16) |
C39 | 0.058 (2) | 0.0492 (19) | 0.0447 (18) | −0.0066 (16) | −0.0066 (15) | −0.0101 (14) |
C40 | 0.0522 (18) | 0.0395 (17) | 0.0426 (17) | −0.0129 (14) | −0.0062 (14) | −0.0032 (13) |
C41 | 0.035 (9) | 0.061 (11) | 0.078 (13) | −0.013 (8) | −0.004 (7) | −0.032 (9) |
C42 | 0.056 (11) | 0.044 (6) | 0.046 (8) | −0.002 (6) | 0.005 (7) | 0.014 (6) |
C43 | 0.054 (10) | 0.100 (14) | 0.086 (13) | −0.018 (10) | −0.001 (9) | −0.002 (11) |
C44 | 0.114 (16) | 0.057 (10) | 0.071 (8) | 0.022 (9) | −0.044 (10) | 0.008 (8) |
C45 | 0.078 (9) | 0.094 (12) | 0.092 (12) | 0.002 (8) | −0.030 (8) | 0.035 (9) |
C46 | 0.108 (13) | 0.076 (14) | 0.060 (9) | −0.008 (10) | −0.037 (9) | 0.016 (8) |
N6 | 0.105 (10) | 0.091 (10) | 0.138 (14) | 0.008 (7) | −0.071 (8) | −0.003 (10) |
C47 | 0.123 (5) | 0.177 (8) | 0.149 (10) | −0.008 (5) | −0.089 (6) | 0.034 (7) |
C48 | 0.122 (10) | 0.142 (5) | 0.133 (7) | 0.028 (6) | −0.069 (8) | 0.020 (5) |
C41' | 0.076 (14) | 0.031 (8) | 0.027 (8) | 0.001 (8) | −0.011 (7) | 0.013 (7) |
C42' | 0.053 (12) | 0.067 (10) | 0.101 (15) | −0.009 (8) | −0.026 (9) | −0.017 (8) |
C43' | 0.067 (11) | 0.053 (7) | 0.090 (13) | 0.014 (8) | −0.028 (10) | −0.004 (8) |
C44' | 0.053 (9) | 0.109 (19) | 0.089 (13) | −0.003 (10) | −0.018 (9) | −0.026 (12) |
C45' | 0.122 (15) | 0.047 (9) | 0.050 (6) | −0.020 (9) | −0.023 (9) | 0.008 (5) |
C46' | 0.054 (8) | 0.041 (10) | 0.057 (8) | −0.019 (7) | 0.003 (7) | 0.006 (7) |
N6' | 0.140 (13) | 0.086 (11) | 0.121 (12) | 0.017 (8) | −0.069 (9) | −0.011 (10) |
C47' | 0.123 (5) | 0.177 (8) | 0.149 (10) | −0.008 (5) | −0.089 (6) | 0.034 (7) |
C48' | 0.122 (10) | 0.142 (5) | 0.133 (7) | 0.028 (6) | −0.069 (8) | 0.020 (5) |
N7 | 0.110 (4) | 0.102 (4) | 0.246 (7) | −0.022 (3) | −0.039 (4) | 0.009 (4) |
C49 | 0.099 (4) | 0.062 (3) | 0.098 (3) | −0.030 (3) | −0.014 (3) | −0.006 (2) |
C50 | 0.106 (4) | 0.112 (4) | 0.171 (6) | −0.036 (3) | −0.037 (4) | −0.049 (4) |
Geometric parameters (Å, º) top
S1—C27 | 1.742 (3) | C25—H25 | 0.9300 |
S1—C29 | 1.826 (3) | C26—H26 | 0.9300 |
O1—C28 | 1.215 (3) | C28—C29 | 1.529 (4) |
O2—C37 | 1.230 (3) | C29—C30 | 1.569 (4) |
N1—C19 | 1.455 (3) | C29—C40 | 1.595 (4) |
N1—C8 | 1.463 (4) | C30—C31 | 1.518 (4) |
N1—C1 | 1.465 (3) | C30—C37 | 1.565 (4) |
N2—C27 | 1.276 (3) | C31—C32 | 1.386 (4) |
N2—C17 | 1.426 (3) | C31—C36 | 1.387 (4) |
N3—C28 | 1.370 (3) | C32—C33 | 1.392 (4) |
N3—C27 | 1.384 (3) | C32—H32 | 0.9300 |
N3—C20 | 1.481 (3) | C33—C34 | 1.376 (5) |
N4—C37 | 1.340 (4) | C33—H33 | 0.9300 |
N4—C36 | 1.404 (4) | C34—C35 | 1.382 (5) |
N4—H4 | 0.83 (3) | C34—H34 | 0.9300 |
N5—C39 | 1.459 (4) | C35—C36 | 1.373 (4) |
N5—C38 | 1.462 (4) | C35—H35 | 0.9300 |
N5—C30 | 1.467 (3) | C38—H38A | 0.9600 |
C1—C2' | 1.468 (4) | C38—H38B | 0.9600 |
C1—C2 | 1.563 (4) | C38—H38C | 0.9600 |
C1—H1A | 0.9600 | C39—C40 | 1.523 (4) |
C1—H1B | 0.9600 | C39—H39A | 0.9700 |
C1—H1C | 0.9600 | C39—H39B | 0.9700 |
C1—H1D | 0.9600 | C40—C41' | 1.514 (6) |
C2—C3 | 1.3900 | C40—C41 | 1.526 (6) |
C2—C7 | 1.3900 | C40—H40A | 0.9601 |
C3—C4 | 1.3900 | C40—H40B | 0.9600 |
C3—H3A | 0.9300 | C41—C42 | 1.3900 |
C4—C5 | 1.3900 | C41—C46 | 1.3900 |
C4—H4A | 0.9300 | C42—C43 | 1.3900 |
C5—C6 | 1.3900 | C42—H42A | 0.9300 |
C5—H5A | 0.9300 | C43—C44 | 1.3900 |
C6—C7 | 1.3900 | C43—H43A | 0.9300 |
C6—H6A | 0.9300 | C44—C45 | 1.3900 |
C7—H7A | 0.9300 | C44—N6 | 1.454 (13) |
C2'—C3' | 1.3900 | C45—C46 | 1.3900 |
C2'—C7' | 1.3900 | C45—H45A | 0.9300 |
C3'—C4' | 1.3900 | C46—H46A | 0.9300 |
C3'—H3'A | 0.9300 | N6—C48 | 1.471 (15) |
C4'—C5' | 1.3900 | N6—C47 | 1.473 (16) |
C4'—H4'A | 0.9300 | C47—H47A | 0.9600 |
C5'—C6' | 1.3900 | C47—H47B | 0.9600 |
C5'—H5'A | 0.9300 | C47—H47C | 0.9600 |
C6'—C7' | 1.3900 | C48—H48A | 0.9600 |
C6'—H6'A | 0.9300 | C48—H48B | 0.9600 |
C7'—H7'A | 0.9300 | C48—H48C | 0.9600 |
C8—C9 | 1.497 (4) | C41'—C42' | 1.3900 |
C8—H8A | 0.9700 | C41'—C46' | 1.3900 |
C8—H8B | 0.9700 | C42'—C43' | 1.3900 |
C9—C10 | 1.337 (4) | C42'—H42B | 0.9300 |
C9—C17 | 1.472 (4) | C43'—C44' | 1.3900 |
C10—C11 | 1.477 (4) | C43'—H43B | 0.9300 |
C10—H10 | 0.9300 | C44'—C45' | 1.3900 |
C11—C16 | 1.377 (5) | C44'—N6' | 1.447 (15) |
C11—C12 | 1.389 (5) | C45'—C46' | 1.3900 |
C12—C13 | 1.390 (6) | C45'—H45B | 0.9300 |
C12—H12 | 0.9300 | C46'—H46B | 0.9300 |
C13—C14 | 1.354 (7) | N6'—C48' | 1.478 (17) |
C13—H13 | 0.9300 | N6'—C47' | 1.488 (16) |
C14—C15 | 1.370 (7) | C47'—H47D | 0.9600 |
C14—H14 | 0.9300 | C47'—H47E | 0.9600 |
C15—C16 | 1.388 (5) | C47'—H47F | 0.9600 |
C15—H15 | 0.9300 | C48'—H48D | 0.9600 |
C16—H16 | 0.9300 | C48'—H48E | 0.9600 |
C17—C18 | 1.342 (4) | C48'—H48F | 0.9600 |
C18—C19 | 1.494 (4) | N7—C49 | 1.113 (5) |
C18—C20 | 1.507 (4) | C49—C50 | 1.435 (5) |
C19—H19A | 0.9700 | C50—H50A | 0.9600 |
C19—H19B | 0.9700 | C50—H50B | 0.9600 |
C20—C21 | 1.517 (4) | C50—H50C | 0.9600 |
C20—H20 | 0.9800 | N8—C51 | 1.129 (9) |
C21—C22 | 1.361 (5) | C51—C52 | 1.510 (9) |
C21—C26 | 1.371 (4) | C52—H52A | 0.9600 |
C22—C23 | 1.387 (6) | C52—H52B | 0.9600 |
C22—H22 | 0.9300 | C52—H52C | 0.9600 |
C23—C24 | 1.353 (7) | N8'—C51' | 1.131 (8) |
C23—H23 | 0.9300 | C51'—C52' | 1.493 (8) |
C24—C25 | 1.344 (7) | C52'—H52D | 0.9600 |
C24—H24 | 0.9300 | C52'—H52E | 0.9600 |
C25—C26 | 1.384 (6) | C52'—H52F | 0.9600 |
| | | |
C27—S1—C29 | 93.47 (12) | C30—C29—C40 | 104.3 (2) |
C19—N1—C8 | 112.1 (2) | C28—C29—S1 | 105.12 (18) |
C19—N1—C1 | 110.0 (2) | C30—C29—S1 | 111.30 (18) |
C8—N1—C1 | 108.4 (2) | C40—C29—S1 | 115.96 (19) |
C27—N2—C17 | 115.7 (2) | N5—C30—C31 | 113.0 (2) |
C28—N3—C27 | 116.9 (2) | N5—C30—C37 | 111.0 (2) |
C28—N3—C20 | 121.2 (2) | C31—C30—C37 | 100.8 (2) |
C27—N3—C20 | 120.3 (2) | N5—C30—C29 | 102.7 (2) |
C37—N4—C36 | 112.0 (3) | C31—C30—C29 | 119.6 (2) |
C37—N4—H4 | 123 (2) | C37—C30—C29 | 109.9 (2) |
C36—N4—H4 | 125 (2) | C32—C31—C36 | 119.1 (3) |
C39—N5—C38 | 114.8 (2) | C32—C31—C30 | 131.9 (3) |
C39—N5—C30 | 106.6 (2) | C36—C31—C30 | 108.9 (2) |
C38—N5—C30 | 115.7 (2) | C31—C32—C33 | 118.8 (3) |
N1—C1—C2' | 118.6 (3) | C31—C32—H32 | 120.6 |
N1—C1—C2 | 110.1 (3) | C33—C32—H32 | 120.6 |
C2'—C1—C2 | 16.0 | C34—C33—C32 | 120.4 (3) |
N1—C1—H1A | 109.6 | C34—C33—H33 | 119.8 |
C2'—C1—H1A | 93.7 | C32—C33—H33 | 119.8 |
C2—C1—H1A | 109.6 | C33—C34—C35 | 121.5 (3) |
N1—C1—H1B | 109.5 | C33—C34—H34 | 119.2 |
C2'—C1—H1B | 115.5 | C35—C34—H34 | 119.2 |
C2—C1—H1B | 109.8 | C36—C35—C34 | 117.3 (3) |
H1A—C1—H1B | 108.3 | C36—C35—H35 | 121.4 |
N1—C1—H1C | 109.6 | C34—C35—H35 | 121.4 |
C2'—C1—H1C | 93.7 | C35—C36—C31 | 122.8 (3) |
C2—C1—H1C | 109.6 | C35—C36—N4 | 127.4 (3) |
H1A—C1—H1C | 0.0 | C31—C36—N4 | 109.8 (3) |
H1B—C1—H1C | 108.3 | O2—C37—N4 | 126.2 (3) |
N1—C1—H1D | 109.5 | O2—C37—C30 | 125.5 (3) |
C2'—C1—H1D | 115.5 | N4—C37—C30 | 108.3 (3) |
C2—C1—H1D | 109.8 | N5—C38—H38A | 109.5 |
H1A—C1—H1D | 108.3 | N5—C38—H38B | 109.5 |
H1B—C1—H1D | 0.0 | H38A—C38—H38B | 109.5 |
H1C—C1—H1D | 108.3 | N5—C38—H38C | 109.5 |
C3—C2—C7 | 120.0 | H38A—C38—H38C | 109.5 |
C3—C2—C1 | 122.2 (3) | H38B—C38—H38C | 109.5 |
C7—C2—C1 | 117.5 (3) | N5—C39—C40 | 103.8 (2) |
C4—C3—C2 | 120.0 | N5—C39—H39A | 111.0 |
C4—C3—H3A | 120.0 | C40—C39—H39A | 111.0 |
C2—C3—H3A | 120.0 | N5—C39—H39B | 111.0 |
C5—C4—C3 | 120.0 | C40—C39—H39B | 111.0 |
C5—C4—H4A | 120.0 | H39A—C39—H39B | 109.0 |
C3—C4—H4A | 120.0 | C41'—C40—C39 | 116.0 (6) |
C4—C5—C6 | 120.0 | C41'—C40—C41 | 5.1 (7) |
C4—C5—H5A | 120.0 | C39—C40—C41 | 119.0 (6) |
C6—C5—H5A | 120.0 | C41'—C40—C29 | 115.9 (7) |
C7—C6—C5 | 120.0 | C39—C40—C29 | 103.6 (2) |
C7—C6—H6A | 120.0 | C41—C40—C29 | 117.6 (7) |
C5—C6—H6A | 120.0 | C41'—C40—H40A | 110.0 |
C6—C7—C2 | 120.0 | C39—C40—H40A | 105.1 |
C6—C7—H7A | 120.0 | C41—C40—H40A | 105.0 |
C2—C7—H7A | 120.0 | C29—C40—H40A | 105.1 |
C3'—C2'—C7' | 120.0 | C41'—C40—H40B | 107.4 |
C3'—C2'—C1 | 115.4 (3) | C39—C40—H40B | 106.6 |
C7'—C2'—C1 | 124.2 (3) | C41—C40—H40B | 102.4 |
C4'—C3'—C2' | 120.0 | C29—C40—H40B | 106.6 |
C4'—C3'—H3'A | 120.0 | H40A—C40—H40B | 2.6 |
C2'—C3'—H3'A | 120.0 | C42—C41—C46 | 120.0 |
C3'—C4'—C5' | 120.0 | C42—C41—C40 | 120.0 (6) |
C3'—C4'—H4'A | 120.0 | C46—C41—C40 | 119.9 (6) |
C5'—C4'—H4'A | 120.0 | C43—C42—C41 | 120.0 |
C6'—C5'—C4' | 120.0 | C43—C42—H42A | 120.0 |
C6'—C5'—H5'A | 120.0 | C41—C42—H42A | 120.0 |
C4'—C5'—H5'A | 120.0 | C42—C43—C44 | 120.0 |
C5'—C6'—C7' | 120.0 | C42—C43—H43A | 120.0 |
C5'—C6'—H6'A | 120.0 | C44—C43—H43A | 120.0 |
C7'—C6'—H6'A | 120.0 | C45—C44—C43 | 120.0 |
C6'—C7'—C2' | 120.0 | C45—C44—N6 | 126.9 (11) |
C6'—C7'—H7'A | 120.0 | C43—C44—N6 | 112.7 (11) |
C2'—C7'—H7'A | 120.0 | C44—C45—C46 | 120.0 |
N1—C8—C9 | 113.7 (2) | C44—C45—H45A | 120.0 |
N1—C8—H8A | 108.8 | C46—C45—H45A | 120.0 |
C9—C8—H8A | 108.8 | C45—C46—C41 | 120.0 |
N1—C8—H8B | 108.8 | C45—C46—H46A | 120.0 |
C9—C8—H8B | 108.8 | C41—C46—H46A | 120.0 |
H8A—C8—H8B | 107.7 | C44—N6—C48 | 115.7 (12) |
C10—C9—C17 | 121.1 (3) | C44—N6—C47 | 119.6 (13) |
C10—C9—C8 | 124.7 (3) | C48—N6—C47 | 114.8 (14) |
C17—C9—C8 | 114.2 (2) | N6—C47—H47A | 109.5 |
C9—C10—C11 | 127.7 (3) | N6—C47—H47B | 109.5 |
C9—C10—H10 | 116.1 | H47A—C47—H47B | 109.5 |
C11—C10—H10 | 116.1 | N6—C47—H47C | 109.5 |
C16—C11—C12 | 117.3 (3) | H47A—C47—H47C | 109.5 |
C16—C11—C10 | 123.8 (3) | H47B—C47—H47C | 109.5 |
C12—C11—C10 | 118.9 (3) | N6—C48—H48A | 109.5 |
C11—C12—C13 | 120.8 (4) | N6—C48—H48B | 109.5 |
C11—C12—H12 | 119.6 | H48A—C48—H48B | 109.5 |
C13—C12—H12 | 119.6 | N6—C48—H48C | 109.5 |
C14—C13—C12 | 120.9 (5) | H48A—C48—H48C | 109.5 |
C14—C13—H13 | 119.5 | H48B—C48—H48C | 109.5 |
C12—C13—H13 | 119.5 | C42'—C41'—C46' | 120.0 |
C13—C14—C15 | 119.2 (4) | C42'—C41'—C40 | 122.9 (6) |
C13—C14—H14 | 120.4 | C46'—C41'—C40 | 117.1 (6) |
C15—C14—H14 | 120.4 | C41'—C42'—C43' | 120.0 |
C14—C15—C16 | 120.4 (4) | C41'—C42'—H42B | 120.0 |
C14—C15—H15 | 119.8 | C43'—C42'—H42B | 120.0 |
C16—C15—H15 | 119.8 | C44'—C43'—C42' | 120.0 |
C11—C16—C15 | 121.4 (4) | C44'—C43'—H43B | 120.0 |
C11—C16—H16 | 119.3 | C42'—C43'—H43B | 120.0 |
C15—C16—H16 | 119.3 | C43'—C44'—C45' | 120.0 |
C18—C17—N2 | 123.0 (2) | C43'—C44'—N6' | 127.0 (13) |
C18—C17—C9 | 120.6 (2) | C45'—C44'—N6' | 112.2 (12) |
N2—C17—C9 | 116.4 (2) | C44'—C45'—C46' | 120.0 |
C17—C18—C19 | 123.2 (2) | C44'—C45'—H45B | 120.0 |
C17—C18—C20 | 121.4 (2) | C46'—C45'—H45B | 120.0 |
C19—C18—C20 | 115.4 (2) | C45'—C46'—C41' | 120.0 |
N1—C19—C18 | 113.4 (2) | C45'—C46'—H46B | 120.0 |
N1—C19—H19A | 108.9 | C41'—C46'—H46B | 120.0 |
C18—C19—H19A | 108.9 | C44'—N6'—C48' | 118.4 (15) |
N1—C19—H19B | 108.9 | C44'—N6'—C47' | 115.2 (13) |
C18—C19—H19B | 108.9 | C48'—N6'—C47' | 114.2 (15) |
H19A—C19—H19B | 107.7 | N6'—C47'—H47D | 109.5 |
N3—C20—C18 | 107.8 (2) | N6'—C47'—H47E | 109.5 |
N3—C20—C21 | 110.2 (2) | H47D—C47'—H47E | 109.5 |
C18—C20—C21 | 113.2 (2) | N6'—C47'—H47F | 109.5 |
N3—C20—H20 | 108.5 | H47D—C47'—H47F | 109.5 |
C18—C20—H20 | 108.5 | H47E—C47'—H47F | 109.5 |
C21—C20—H20 | 108.5 | N6'—C48'—H48D | 109.5 |
C22—C21—C26 | 118.7 (3) | N6'—C48'—H48E | 109.5 |
C22—C21—C20 | 120.5 (3) | H48D—C48'—H48E | 109.5 |
C26—C21—C20 | 120.8 (3) | N6'—C48'—H48F | 109.5 |
C21—C22—C23 | 120.3 (4) | H48D—C48'—H48F | 109.5 |
C21—C22—H22 | 119.9 | H48E—C48'—H48F | 109.5 |
C23—C22—H22 | 119.9 | N7—C49—C50 | 179.6 (6) |
C24—C23—C22 | 120.9 (5) | C49—C50—H50A | 109.5 |
C24—C23—H23 | 119.6 | C49—C50—H50B | 109.5 |
C22—C23—H23 | 119.6 | H50A—C50—H50B | 109.5 |
C25—C24—C23 | 118.9 (4) | C49—C50—H50C | 109.5 |
C25—C24—H24 | 120.6 | H50A—C50—H50C | 109.5 |
C23—C24—H24 | 120.6 | H50B—C50—H50C | 109.5 |
C24—C25—C26 | 121.4 (5) | N8—C51—C52 | 157 (2) |
C24—C25—H25 | 119.3 | C51—C52—H52A | 109.5 |
C26—C25—H25 | 119.3 | C51—C52—H52B | 109.5 |
C21—C26—C25 | 119.9 (4) | H52A—C52—H52B | 109.5 |
C21—C26—H26 | 120.1 | C51—C52—H52C | 109.5 |
C25—C26—H26 | 120.1 | H52A—C52—H52C | 109.5 |
N2—C27—N3 | 125.9 (2) | H52B—C52—H52C | 109.5 |
N2—C27—S1 | 122.7 (2) | N8'—C51'—C52' | 158.5 (15) |
N3—C27—S1 | 111.36 (19) | C51'—C52'—H52D | 109.5 |
O1—C28—N3 | 122.6 (2) | C51'—C52'—H52E | 109.5 |
O1—C28—C29 | 124.4 (2) | H52D—C52'—H52E | 109.5 |
N3—C28—C29 | 113.0 (2) | C51'—C52'—H52F | 109.5 |
C28—C29—C30 | 113.4 (2) | H52D—C52'—H52F | 109.5 |
C28—C29—C40 | 106.9 (2) | H52E—C52'—H52F | 109.5 |
| | | |
C19—N1—C1—C2' | 61.5 (6) | C27—S1—C29—C40 | −114.4 (2) |
C8—N1—C1—C2' | −175.6 (5) | C39—N5—C30—C31 | −170.7 (2) |
C19—N1—C1—C2 | 76.3 (4) | C38—N5—C30—C31 | 60.4 (3) |
C8—N1—C1—C2 | −160.8 (4) | C39—N5—C30—C37 | 76.9 (3) |
N1—C1—C2—C3 | 51.3 (5) | C38—N5—C30—C37 | −52.1 (3) |
C2'—C1—C2—C3 | 176.51 (6) | C39—N5—C30—C29 | −40.5 (3) |
N1—C1—C2—C7 | −135.4 (4) | C38—N5—C30—C29 | −169.5 (2) |
C2'—C1—C2—C7 | −10.1 (2) | C28—C29—C30—N5 | −95.6 (3) |
C7—C2—C3—C4 | 0.0 | C40—C29—C30—N5 | 20.4 (3) |
C1—C2—C3—C4 | 173.2 (3) | S1—C29—C30—N5 | 146.13 (18) |
C2—C3—C4—C5 | 0.0 | C28—C29—C30—C31 | 30.4 (3) |
C3—C4—C5—C6 | 0.0 | C40—C29—C30—C31 | 146.4 (2) |
C4—C5—C6—C7 | 0.0 | S1—C29—C30—C31 | −87.9 (3) |
C5—C6—C7—C2 | 0.0 | C28—C29—C30—C37 | 146.2 (2) |
C3—C2—C7—C6 | 0.0 | C40—C29—C30—C37 | −97.8 (2) |
C1—C2—C7—C6 | −173.5 (3) | S1—C29—C30—C37 | 27.9 (3) |
N1—C1—C2'—C3' | 66.2 (6) | N5—C30—C31—C32 | 60.9 (4) |
C2—C1—C2'—C3' | 5.32 (9) | C37—C30—C31—C32 | 179.4 (3) |
N1—C1—C2'—C7' | −120.5 (5) | C29—C30—C31—C32 | −60.1 (4) |
C2—C1—C2'—C7' | 178.57 (18) | N5—C30—C31—C36 | −114.9 (3) |
C7'—C2'—C3'—C4' | 0.0 | C37—C30—C31—C36 | 3.6 (3) |
C1—C2'—C3'—C4' | 173.6 (3) | C29—C30—C31—C36 | 124.1 (3) |
C2'—C3'—C4'—C5' | 0.0 | C36—C31—C32—C33 | −2.3 (4) |
C3'—C4'—C5'—C6' | 0.0 | C30—C31—C32—C33 | −177.8 (3) |
C4'—C5'—C6'—C7' | 0.0 | C31—C32—C33—C34 | 2.4 (5) |
C5'—C6'—C7'—C2' | 0.0 | C32—C33—C34—C35 | −0.7 (5) |
C3'—C2'—C7'—C6' | 0.0 | C33—C34—C35—C36 | −1.1 (5) |
C1—C2'—C7'—C6' | −173.0 (3) | C34—C35—C36—C31 | 1.2 (4) |
C19—N1—C8—C9 | −56.2 (3) | C34—C35—C36—N4 | 179.9 (3) |
C1—N1—C8—C9 | −177.8 (2) | C32—C31—C36—C35 | 0.5 (4) |
N1—C8—C9—C10 | −140.2 (3) | C30—C31—C36—C35 | 176.9 (3) |
N1—C8—C9—C17 | 39.6 (3) | C32—C31—C36—N4 | −178.4 (2) |
C17—C9—C10—C11 | −179.1 (3) | C30—C31—C36—N4 | −2.0 (3) |
C8—C9—C10—C11 | 0.7 (5) | C37—N4—C36—C35 | −179.8 (3) |
C9—C10—C11—C16 | −44.2 (5) | C37—N4—C36—C31 | −0.9 (3) |
C9—C10—C11—C12 | 137.2 (4) | C36—N4—C37—O2 | −178.9 (3) |
C16—C11—C12—C13 | 1.5 (6) | C36—N4—C37—C30 | 3.3 (3) |
C10—C11—C12—C13 | −179.8 (4) | N5—C30—C37—O2 | −62.0 (4) |
C11—C12—C13—C14 | −1.7 (7) | C31—C30—C37—O2 | 178.1 (3) |
C12—C13—C14—C15 | 1.2 (7) | C29—C30—C37—O2 | 50.9 (4) |
C13—C14—C15—C16 | −0.6 (7) | N5—C30—C37—N4 | 115.8 (3) |
C12—C11—C16—C15 | −0.9 (5) | C31—C30—C37—N4 | −4.1 (3) |
C10—C11—C16—C15 | −179.5 (3) | C29—C30—C37—N4 | −131.3 (2) |
C14—C15—C16—C11 | 0.4 (6) | C38—N5—C39—C40 | 174.3 (3) |
C27—N2—C17—C18 | 11.3 (4) | C30—N5—C39—C40 | 44.8 (3) |
C27—N2—C17—C9 | −166.2 (2) | N5—C39—C40—C41' | −157.3 (7) |
C10—C9—C17—C18 | 167.9 (3) | N5—C39—C40—C41 | −161.8 (7) |
C8—C9—C17—C18 | −11.9 (4) | N5—C39—C40—C29 | −29.0 (3) |
C10—C9—C17—N2 | −14.5 (4) | C28—C29—C40—C41' | −106.2 (5) |
C8—C9—C17—N2 | 165.7 (2) | C30—C29—C40—C41' | 133.3 (5) |
N2—C17—C18—C19 | −176.9 (3) | S1—C29—C40—C41' | 10.6 (5) |
C9—C17—C18—C19 | 0.6 (4) | C28—C29—C40—C39 | 125.5 (2) |
N2—C17—C18—C20 | 3.6 (4) | C30—C29—C40—C39 | 5.1 (3) |
C9—C17—C18—C20 | −178.9 (2) | S1—C29—C40—C39 | −117.7 (2) |
C8—N1—C19—C18 | 43.4 (3) | C28—C29—C40—C41 | −100.9 (5) |
C1—N1—C19—C18 | 164.1 (2) | C30—C29—C40—C41 | 138.7 (5) |
C17—C18—C19—N1 | −16.5 (4) | S1—C29—C40—C41 | 15.9 (5) |
C20—C18—C19—N1 | 163.0 (2) | C41'—C40—C41—C42 | −9 (15) |
C28—N3—C20—C18 | −168.2 (2) | C39—C40—C41—C42 | 45.5 (14) |
C27—N3—C20—C18 | 26.7 (3) | C29—C40—C41—C42 | −80.9 (12) |
C28—N3—C20—C21 | 67.7 (3) | C41'—C40—C41—C46 | 170 (16) |
C27—N3—C20—C21 | −97.4 (3) | C39—C40—C41—C46 | −135.6 (8) |
C17—C18—C20—N3 | −21.2 (4) | C29—C40—C41—C46 | 98.0 (10) |
C19—C18—C20—N3 | 159.3 (2) | C46—C41—C42—C43 | 0.0 |
C17—C18—C20—C21 | 101.0 (3) | C40—C41—C42—C43 | 178.9 (15) |
C19—C18—C20—C21 | −78.5 (3) | C41—C42—C43—C44 | 0.0 |
N3—C20—C21—C22 | 72.9 (4) | C42—C43—C44—C45 | 0.0 |
C18—C20—C21—C22 | −47.9 (4) | C42—C43—C44—N6 | −173 (2) |
N3—C20—C21—C26 | −105.0 (3) | C43—C44—C45—C46 | 0.0 |
C18—C20—C21—C26 | 134.1 (3) | N6—C44—C45—C46 | 172 (2) |
C26—C21—C22—C23 | 0.8 (6) | C44—C45—C46—C41 | 0.0 |
C20—C21—C22—C23 | −177.2 (3) | C42—C41—C46—C45 | 0.0 |
C21—C22—C23—C24 | −1.8 (7) | C40—C41—C46—C45 | −178.9 (15) |
C22—C23—C24—C25 | 1.7 (8) | C45—C44—N6—C48 | 40 (3) |
C23—C24—C25—C26 | −0.8 (8) | C43—C44—N6—C48 | −147 (2) |
C22—C21—C26—C25 | 0.1 (5) | C45—C44—N6—C47 | −176.0 (19) |
C20—C21—C26—C25 | 178.1 (3) | C43—C44—N6—C47 | −3 (3) |
C24—C25—C26—C21 | −0.2 (7) | C39—C40—C41'—C42' | 45.6 (13) |
C17—N2—C27—N3 | −5.5 (4) | C41—C40—C41'—C42' | 174 (16) |
C17—N2—C27—S1 | 171.8 (2) | C29—C40—C41'—C42' | −76.3 (12) |
C28—N3—C27—N2 | 179.0 (3) | C39—C40—C41'—C46' | −133.0 (8) |
C20—N3—C27—N2 | −15.2 (4) | C41—C40—C41'—C46' | −5 (15) |
C28—N3—C27—S1 | 1.5 (3) | C29—C40—C41'—C46' | 105.1 (9) |
C20—N3—C27—S1 | 167.24 (19) | C46'—C41'—C42'—C43' | 0.0 |
C29—S1—C27—N2 | 179.4 (2) | C40—C41'—C42'—C43' | −178.6 (16) |
C29—S1—C27—N3 | −3.0 (2) | C41'—C42'—C43'—C44' | 0.0 |
C27—N3—C28—O1 | 177.6 (3) | C42'—C43'—C44'—C45' | 0.0 |
C20—N3—C28—O1 | 12.0 (4) | C42'—C43'—C44'—N6' | 169 (2) |
C27—N3—C28—C29 | 1.3 (3) | C43'—C44'—C45'—C46' | 0.0 |
C20—N3—C28—C29 | −164.3 (2) | N6'—C44'—C45'—C46' | −171 (2) |
O1—C28—C29—C30 | 58.7 (4) | C44'—C45'—C46'—C41' | 0.0 |
N3—C28—C29—C30 | −125.1 (2) | C42'—C41'—C46'—C45' | 0.0 |
O1—C28—C29—C40 | −55.7 (4) | C40—C41'—C46'—C45' | 178.7 (15) |
N3—C28—C29—C40 | 120.5 (2) | C43'—C44'—N6'—C48' | 179.1 (18) |
O1—C28—C29—S1 | −179.4 (2) | C45'—C44'—N6'—C48' | −11 (3) |
N3—C28—C29—S1 | −3.3 (3) | C43'—C44'—N6'—C47' | 39 (3) |
C27—S1—C29—C28 | 3.4 (2) | C45'—C44'—N6'—C47' | −151 (2) |
C27—S1—C29—C30 | 126.6 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O2i | 0.83 (3) | 2.06 (3) | 2.885 (3) | 169 (3) |
Symmetry code: (i) −x+1, −y+2, −z. |