The majority of the title molecule, C
28H
34ClN
3O
9S, is disordered over two closely spaced sets of sites; the site occupancy of the major component = 0.542 (3). The conformation of each component is approximately U-shaped with the chlorobenzene ring forming the base and the indolinyl and sulfamoyl groups the sides; an intramolecular C—H
Cl hydrogen bond possibly contributes to the stabilization of the conformation. In the crystal, a corrugated layer structure parallel to the
ab plane is formed by C—H
O and C—H
Cl hydrogen bonds together with C—H
π(ring) interactions.
Supporting information
CCDC reference: 2280340
Key indicators
Structure: I
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.006 Å
- Disorder in main residue
- R factor = 0.056
- wR factor = 0.154
- Data-to-parameter ratio = 17.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT220_ALERT_2_C NonSolvent Resd 1 C Ueq(max)/Ueq(min) Range 3.2 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00633 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 2 Report
Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 58 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ... 57 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records 28 Report
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records 2 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records 4 Report
PLAT186_ALERT_4_G The CIF-Embedded .res File Contains ISOR Records 2 Report
PLAT189_ALERT_3_G A Non-default SAME Restraint Value for First Par 0.0030 Report
PLAT189_ALERT_3_G A Non-default SAME Restraint Value for First Par 0.0030 Report
PLAT191_ALERT_3_G A Non-default SADI Restraint Value has been used 0.0030 Report
PLAT191_ALERT_3_G A Non-default SADI Restraint Value has been used 0.0030 Report
PLAT191_ALERT_3_G A Non-default SADI Restraint Value has been used 0.0030 Report
PLAT191_ALERT_3_G A Non-default SADI Restraint Value has been used 0.0030 Report
PLAT230_ALERT_2_G Hirshfeld Test Diff for N1 --N2 . 11.5 s.u.
PLAT301_ALERT_3_G Main Residue Disorder ..............(Resd 1 ) 67% Note
PLAT432_ALERT_2_G Short Inter X...Y Contact O5 ..C22 . 2.85 Ang.
1-x,1/2+y,1-z = 2_656 Check
PLAT480_ALERT_4_G Long H...A H-Bond Reported H10A ..CL1 . 2.88 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H24A ..CL1 . 2.86 Ang.
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms .... ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 413 Note
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL 2019/3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 31 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 10 Info
PLAT992_ALERT_5_G Repd & Actual _reflns_number_gt Values Differ by 2 Check
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
24 ALERT level G = General information/check it is not something unexpected
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 ALERT type 2 Indicator that the structure model may be wrong or deficient
10 ALERT type 3 Indicator that the structure quality may be low
8 ALERT type 4 Improvement, methodology, query or suggestion
2 ALERT type 5 Informative message, check
Data collection: APEX3 (Bruker, 2020); cell refinement: SAINT (Bruker, 2020); data reduction: SAINT (Bruker, 2020); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
Diethyl
2,2'-[({2-chloro-5-[(2-ethoxy-2-oxoethyl)(2-methylindolin-1-yl)carbamoyl]phenyl}sulfonyl)azanediyl]diacetate
top
Crystal data top
C28H34ClN3O9S | F(000) = 656 |
Mr = 624.09 | Dx = 1.358 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.683 (2) Å | Cell parameters from 8512 reflections |
b = 11.347 (2) Å | θ = 2.4–26.5° |
c = 13.203 (3) Å | µ = 0.25 mm−1 |
β = 107.491 (3)° | T = 150 K |
V = 1526.4 (6) Å3 | Plate, colourless |
Z = 2 | 0.36 × 0.26 × 0.06 mm |
Data collection top
Bruker SMART APEX CCD Diffractometer | 5986 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.040 |
φ and ω scans | θmax = 28.7°, θmin = 1.6° |
Absorption correction: numerical (SADABS; Krause et al., 2015) | h = −14→14 |
Tmin = 0.92, Tmax = 0.98 | k = −15→15 |
26691 measured reflections | l = −17→17 |
7798 independent reflections | |
Refinement top
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)] = 0.056 | H-atom parameters constrained |
wR(F2) = 0.154 | w = 1/[σ2(Fo2) + (0.0951P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
7798 reflections | Δρmax = 0.67 e Å−3 |
448 parameters | Δρmin = −0.45 e Å−3 |
413 restraints | Absolute structure: Flack x determined using 2312 quotients
[(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
Primary atom site location: dual | Absolute structure parameter: 0.07 (3) |
Special details top
Experimental. The diffraction data were obtained from 3 sets of 400 frames,
each of width 0.5 deg. in omega, collected at phi = 0.00,
90.00 and 180.00 deg. and 2 sets of 800 frames, each of
width 0.45 deg in phi, collected at omega = -30.00 and 210.00
deg. The scan time was 25 sec/frame. |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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 > 2sigma(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. H-atoms attached to carbon
were placed in calculated positions (C—H = 0.95 - 1.00 Å). All were
included as riding contributions with isotropic displacement parameters
1.2 - 1.5 times those of the attached atoms. The ethyl 4-chlorobenzyl-N-
(2-methylindolin-1-yl)glycinate portion of the molecule is disordered
over two partially resolved sites in a 0.542 (3):0.458 (3) ratio. Also, the
C23—C24 ethyl group is disordered over two sites in a 0.526 (12):0.474 (12)
ratio. The two components of each disorder were refined with restraints that
their geometries be comparable. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
S1 | 0.60808 (8) | 0.54611 (11) | 0.44326 (6) | 0.0246 (2) | |
O4 | 0.7476 (2) | 0.5529 (3) | 0.47429 (18) | 0.0310 (5) | |
O5 | 0.5355 (3) | 0.6319 (2) | 0.4804 (2) | 0.0342 (7) | |
O6 | 0.6174 (3) | 0.1476 (3) | 0.3450 (3) | 0.0420 (7) | |
O7 | 0.4485 (3) | 0.2752 (3) | 0.3126 (2) | 0.0370 (7) | |
O8 | 0.6303 (3) | 0.3898 (4) | 0.6935 (3) | 0.0494 (8) | |
O9 | 0.4203 (3) | 0.3672 (3) | 0.6856 (2) | 0.0401 (7) | |
N3 | 0.5647 (3) | 0.4184 (3) | 0.4747 (3) | 0.0278 (7) | |
Cl1 | 0.2994 (7) | 0.5368 (15) | 0.2927 (7) | 0.0376 (19) | 0.542 (3) |
O1 | 0.7150 (6) | 0.5773 (6) | 0.0047 (4) | 0.0422 (15) | 0.542 (3) |
O2 | 0.9930 (6) | 0.7129 (5) | 0.1760 (5) | 0.0367 (12) | 0.542 (3) |
O3 | 1.0605 (7) | 0.6851 (7) | 0.0338 (5) | 0.0565 (15) | 0.542 (3) |
N1 | 0.8695 (6) | 0.3963 (4) | 0.2179 (4) | 0.0314 (9) | 0.542 (3) |
N2 | 0.8544 (5) | 0.4813 (6) | 0.1379 (5) | 0.0395 (13) | 0.542 (3) |
C1 | 0.9622 (11) | 0.4182 (5) | 0.3174 (6) | 0.0283 (10) | 0.542 (3) |
C2 | 1.0092 (19) | 0.5264 (5) | 0.3612 (9) | 0.0316 (11) | 0.542 (3) |
H2 | 0.982257 | 0.597547 | 0.322925 | 0.038* | 0.542 (3) |
C3 | 1.0976 (8) | 0.5272 (8) | 0.4634 (6) | 0.0342 (15) | 0.542 (3) |
H3 | 1.134539 | 0.598990 | 0.495918 | 0.041* | 0.542 (3) |
C4 | 1.1314 (7) | 0.4175 (8) | 0.5180 (6) | 0.0369 (15) | 0.542 (3) |
H4 | 1.189407 | 0.417708 | 0.588456 | 0.044* | 0.542 (3) |
C5 | 1.0830 (9) | 0.3126 (8) | 0.4724 (7) | 0.0425 (17) | 0.542 (3) |
H5 | 1.108653 | 0.240573 | 0.509459 | 0.051* | 0.542 (3) |
C6 | 0.9974 (8) | 0.3133 (6) | 0.3727 (6) | 0.0314 (14) | 0.542 (3) |
C7 | 0.9270 (9) | 0.2123 (6) | 0.3051 (7) | 0.0381 (14) | 0.542 (3) |
H7A | 0.854404 | 0.182872 | 0.330333 | 0.046* | 0.542 (3) |
H7B | 0.988117 | 0.146556 | 0.305549 | 0.046* | 0.542 (3) |
C8 | 0.8748 (7) | 0.2658 (6) | 0.1947 (6) | 0.0344 (14) | 0.542 (3) |
H8 | 0.941488 | 0.253357 | 0.156400 | 0.041* | 0.542 (3) |
C9 | 0.7445 (9) | 0.2209 (8) | 0.1255 (7) | 0.0489 (17) | 0.542 (3) |
H9A | 0.718893 | 0.264456 | 0.058359 | 0.073* | 0.542 (3) |
H9B | 0.677899 | 0.232090 | 0.162047 | 0.073* | 0.542 (3) |
H9C | 0.751849 | 0.136822 | 0.111242 | 0.073* | 0.542 (3) |
C10 | 0.9664 (7) | 0.5244 (8) | 0.0989 (6) | 0.0462 (19) | 0.542 (3) |
H10A | 1.046523 | 0.485052 | 0.144029 | 0.055* | 0.542 (3) |
H10B | 0.950032 | 0.491760 | 0.026578 | 0.055* | 0.542 (3) |
C11 | 1.0005 (8) | 0.6456 (7) | 0.0928 (6) | 0.0353 (15) | 0.542 (3) |
C12 | 1.0536 (11) | 0.8298 (9) | 0.1908 (8) | 0.0491 (19) | 0.542 (3) |
H12A | 0.999331 | 0.885773 | 0.138173 | 0.059* | 0.542 (3) |
H12B | 1.141981 | 0.826142 | 0.181313 | 0.059* | 0.542 (3) |
C13 | 1.0631 (11) | 0.8686 (9) | 0.2997 (9) | 0.056 (2) | 0.542 (3) |
H13A | 1.118669 | 0.938905 | 0.317384 | 0.084* | 0.542 (3) |
H13B | 1.101680 | 0.805386 | 0.350035 | 0.084* | 0.542 (3) |
H13C | 0.975245 | 0.887158 | 0.304028 | 0.084* | 0.542 (3) |
C14 | 0.7348 (5) | 0.5262 (7) | 0.0897 (4) | 0.0273 (13) | 0.542 (3) |
C15 | 0.6294 (4) | 0.5271 (5) | 0.1450 (3) | 0.0241 (12) | 0.542 (3) |
C16 | 0.6595 (4) | 0.5333 (6) | 0.2548 (3) | 0.0229 (12) | 0.542 (3) |
H16 | 0.748523 | 0.535298 | 0.297764 | 0.028* | 0.542 (3) |
C17 | 0.5593 (5) | 0.5365 (6) | 0.30187 (19) | 0.0211 (11) | 0.542 (3) |
C18 | 0.4290 (5) | 0.5335 (6) | 0.2390 (3) | 0.0276 (13) | 0.542 (3) |
C19 | 0.3989 (4) | 0.5273 (6) | 0.1292 (3) | 0.0313 (14) | 0.542 (3) |
H19 | 0.309902 | 0.525314 | 0.086237 | 0.038* | 0.542 (3) |
C20 | 0.4991 (4) | 0.5242 (5) | 0.08213 (19) | 0.0301 (13) | 0.542 (3) |
H20 | 0.478550 | 0.519962 | 0.007036 | 0.036* | 0.542 (3) |
Cl1A | 0.2959 (9) | 0.5595 (18) | 0.2923 (8) | 0.0376 (19) | 0.458 (3) |
O1A | 0.7240 (7) | 0.6425 (7) | 0.0167 (5) | 0.0422 (15) | 0.458 (3) |
O2A | 0.9978 (7) | 0.6768 (6) | 0.1420 (6) | 0.0367 (12) | 0.458 (3) |
O3A | 1.0740 (8) | 0.6132 (8) | 0.0093 (6) | 0.0565 (15) | 0.458 (3) |
N1A | 0.8383 (6) | 0.4156 (5) | 0.2036 (4) | 0.0314 (9) | 0.458 (3) |
N2A | 0.8422 (6) | 0.5135 (6) | 0.1379 (5) | 0.0395 (13) | 0.458 (3) |
C1A | 0.9428 (13) | 0.4089 (5) | 0.2993 (7) | 0.0283 (10) | 0.458 (3) |
C2A | 1.008 (2) | 0.5001 (6) | 0.3632 (11) | 0.0316 (11) | 0.458 (3) |
H2A | 0.992996 | 0.579694 | 0.340541 | 0.038* | 0.458 (3) |
C3A | 1.0957 (10) | 0.4718 (9) | 0.4620 (7) | 0.0342 (15) | 0.458 (3) |
H3A | 1.140601 | 0.531675 | 0.509339 | 0.041* | 0.458 (3) |
C4A | 1.1160 (10) | 0.3498 (9) | 0.4900 (7) | 0.0369 (15) | 0.458 (3) |
H4A | 1.177243 | 0.329063 | 0.556131 | 0.044* | 0.458 (3) |
C5A | 1.0501 (10) | 0.2627 (8) | 0.4244 (8) | 0.0425 (17) | 0.458 (3) |
H5A | 1.062510 | 0.182548 | 0.445958 | 0.051* | 0.458 (3) |
C6A | 0.9667 (9) | 0.2915 (6) | 0.3282 (7) | 0.0314 (14) | 0.458 (3) |
C7A | 0.8798 (9) | 0.2147 (6) | 0.2421 (8) | 0.0381 (14) | 0.458 (3) |
H7C | 0.803112 | 0.185759 | 0.262288 | 0.046* | 0.458 (3) |
H7D | 0.928945 | 0.146341 | 0.226989 | 0.046* | 0.458 (3) |
C8A | 0.8374 (8) | 0.2972 (7) | 0.1472 (7) | 0.0344 (14) | 0.458 (3) |
H8A | 0.905918 | 0.297988 | 0.109635 | 0.041* | 0.458 (3) |
C9A | 0.7047 (9) | 0.2781 (9) | 0.0680 (8) | 0.0489 (17) | 0.458 (3) |
H9D | 0.687923 | 0.339864 | 0.013628 | 0.073* | 0.458 (3) |
H9E | 0.637145 | 0.281223 | 0.104319 | 0.073* | 0.458 (3) |
H9F | 0.702486 | 0.200856 | 0.034308 | 0.073* | 0.458 (3) |
C10A | 0.9400 (9) | 0.4912 (8) | 0.0750 (7) | 0.0462 (19) | 0.458 (3) |
H10C | 0.997541 | 0.424066 | 0.106883 | 0.055* | 0.458 (3) |
H10D | 0.891210 | 0.470055 | 0.000840 | 0.055* | 0.458 (3) |
C11A | 1.0188 (8) | 0.5934 (9) | 0.0752 (7) | 0.0353 (15) | 0.458 (3) |
C12A | 1.0608 (11) | 0.7912 (9) | 0.1428 (10) | 0.0491 (19) | 0.458 (3) |
H12C | 1.021000 | 0.833033 | 0.074944 | 0.059* | 0.458 (3) |
H12D | 1.155707 | 0.780818 | 0.152451 | 0.059* | 0.458 (3) |
C13A | 1.0410 (13) | 0.8592 (10) | 0.2321 (12) | 0.056 (2) | 0.458 (3) |
H13D | 1.073716 | 0.939632 | 0.230606 | 0.084* | 0.458 (3) |
H13E | 1.088938 | 0.821364 | 0.299294 | 0.084* | 0.458 (3) |
H13F | 0.947231 | 0.861575 | 0.225608 | 0.084* | 0.458 (3) |
C14A | 0.7347 (6) | 0.5776 (9) | 0.0926 (5) | 0.0273 (13) | 0.458 (3) |
C15A | 0.6263 (5) | 0.5714 (6) | 0.1452 (3) | 0.0241 (12) | 0.458 (3) |
C16A | 0.6562 (5) | 0.5654 (7) | 0.2550 (3) | 0.0229 (12) | 0.458 (3) |
H16A | 0.745202 | 0.563497 | 0.298079 | 0.028* | 0.458 (3) |
C17A | 0.5559 (6) | 0.5623 (8) | 0.3020 (2) | 0.0211 (11) | 0.458 (3) |
C18A | 0.4257 (6) | 0.5651 (8) | 0.2390 (4) | 0.0276 (13) | 0.458 (3) |
C19A | 0.3958 (4) | 0.5711 (7) | 0.1291 (3) | 0.0313 (14) | 0.458 (3) |
H19A | 0.306771 | 0.573059 | 0.086099 | 0.038* | 0.458 (3) |
C20A | 0.4961 (5) | 0.5743 (7) | 0.0822 (2) | 0.0301 (13) | 0.458 (3) |
H20A | 0.475641 | 0.578374 | 0.007135 | 0.036* | 0.458 (3) |
C21 | 0.6376 (4) | 0.3145 (3) | 0.4586 (3) | 0.0301 (8) | |
H21A | 0.659298 | 0.266133 | 0.524055 | 0.036* | |
H21B | 0.721346 | 0.340976 | 0.448656 | 0.036* | |
C22 | 0.5672 (4) | 0.2368 (3) | 0.3654 (3) | 0.0324 (9) | |
C23 | 0.3658 (10) | 0.1945 (11) | 0.2343 (10) | 0.040 (2) | 0.526 (12) |
H23A | 0.355884 | 0.119007 | 0.268714 | 0.048* | 0.526 (12) |
H23B | 0.406677 | 0.177976 | 0.177690 | 0.048* | 0.526 (12) |
C24 | 0.2319 (10) | 0.2520 (12) | 0.1868 (11) | 0.058 (2) | 0.526 (12) |
H24A | 0.243520 | 0.331157 | 0.161230 | 0.088* | 0.526 (12) |
H24B | 0.186810 | 0.257710 | 0.241208 | 0.088* | 0.526 (12) |
H24C | 0.179278 | 0.204217 | 0.127370 | 0.088* | 0.526 (12) |
C23A | 0.3757 (11) | 0.2112 (15) | 0.2169 (10) | 0.040 (2) | 0.474 (12) |
H23C | 0.417236 | 0.134334 | 0.211744 | 0.048* | 0.474 (12) |
H23D | 0.368740 | 0.257769 | 0.152071 | 0.048* | 0.474 (12) |
C24A | 0.2418 (12) | 0.1949 (14) | 0.2341 (12) | 0.058 (2) | 0.474 (12) |
H24D | 0.206690 | 0.271934 | 0.245321 | 0.088* | 0.474 (12) |
H24E | 0.251091 | 0.145121 | 0.296619 | 0.088* | 0.474 (12) |
H24F | 0.181707 | 0.157156 | 0.171493 | 0.088* | 0.474 (12) |
C25 | 0.4624 (4) | 0.4050 (3) | 0.5260 (3) | 0.0283 (8) | |
H25A | 0.405925 | 0.337290 | 0.493872 | 0.034* | |
H25B | 0.406843 | 0.476623 | 0.512948 | 0.034* | |
C26 | 0.5177 (4) | 0.3856 (4) | 0.6440 (3) | 0.0337 (9) | |
C27 | 0.4571 (5) | 0.3598 (6) | 0.8008 (4) | 0.0537 (13) | |
H27A | 0.514494 | 0.426712 | 0.833385 | 0.064* | |
H27B | 0.504902 | 0.285421 | 0.825727 | 0.064* | |
C28 | 0.3319 (6) | 0.3635 (6) | 0.8307 (5) | 0.0665 (18) | |
H28A | 0.288818 | 0.439891 | 0.810204 | 0.100* | |
H28B | 0.351927 | 0.352855 | 0.907560 | 0.100* | |
H28C | 0.273308 | 0.300324 | 0.793714 | 0.100* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0278 (4) | 0.0230 (4) | 0.0258 (4) | −0.0039 (4) | 0.0123 (3) | −0.0033 (4) |
O4 | 0.0294 (13) | 0.0345 (13) | 0.0293 (11) | −0.0110 (13) | 0.0093 (10) | −0.0042 (12) |
O5 | 0.0490 (18) | 0.0239 (13) | 0.0383 (15) | 0.0003 (12) | 0.0263 (14) | −0.0012 (11) |
O6 | 0.0490 (18) | 0.0275 (15) | 0.057 (2) | 0.0010 (13) | 0.0278 (15) | −0.0112 (13) |
O7 | 0.0382 (17) | 0.0319 (15) | 0.0413 (16) | −0.0013 (12) | 0.0123 (13) | −0.0134 (12) |
O8 | 0.0308 (18) | 0.079 (3) | 0.0393 (17) | −0.0068 (16) | 0.0117 (14) | −0.0076 (16) |
O9 | 0.0353 (17) | 0.0540 (19) | 0.0361 (16) | −0.0125 (14) | 0.0186 (13) | −0.0095 (14) |
N3 | 0.0320 (18) | 0.0217 (15) | 0.0363 (17) | −0.0046 (12) | 0.0202 (14) | −0.0060 (13) |
Cl1 | 0.0236 (5) | 0.053 (6) | 0.0403 (5) | 0.0055 (13) | 0.0156 (4) | 0.0047 (14) |
O1 | 0.037 (2) | 0.062 (4) | 0.029 (2) | 0.000 (3) | 0.0123 (17) | 0.004 (2) |
O2 | 0.0313 (18) | 0.052 (3) | 0.034 (3) | 0.001 (2) | 0.020 (2) | 0.000 (2) |
O3 | 0.052 (3) | 0.087 (4) | 0.047 (3) | 0.003 (3) | 0.039 (2) | 0.005 (3) |
N1 | 0.0309 (10) | 0.0318 (10) | 0.0317 (10) | 0.0006 (4) | 0.0097 (5) | −0.0010 (4) |
N2 | 0.025 (2) | 0.068 (3) | 0.0295 (17) | 0.0047 (19) | 0.0131 (15) | −0.008 (2) |
C1 | 0.018 (3) | 0.035 (2) | 0.033 (2) | −0.0011 (16) | 0.0099 (19) | −0.0027 (17) |
C2 | 0.0267 (19) | 0.036 (3) | 0.0322 (18) | 0.000 (3) | 0.0094 (16) | 0.002 (2) |
C3 | 0.028 (2) | 0.040 (4) | 0.036 (2) | −0.001 (3) | 0.0118 (18) | −0.005 (3) |
C4 | 0.027 (3) | 0.050 (3) | 0.033 (3) | 0.007 (3) | 0.007 (2) | 0.004 (2) |
C5 | 0.038 (3) | 0.043 (3) | 0.048 (3) | 0.009 (3) | 0.014 (3) | 0.004 (2) |
C6 | 0.029 (3) | 0.033 (3) | 0.035 (3) | 0.002 (2) | 0.013 (3) | −0.007 (2) |
C7 | 0.039 (3) | 0.033 (2) | 0.044 (3) | 0.001 (2) | 0.015 (3) | −0.007 (3) |
C8 | 0.031 (3) | 0.040 (3) | 0.032 (3) | 0.005 (2) | 0.010 (2) | −0.007 (2) |
C9 | 0.048 (4) | 0.049 (4) | 0.048 (4) | −0.010 (3) | 0.012 (3) | −0.016 (3) |
C10 | 0.032 (3) | 0.080 (4) | 0.028 (3) | −0.015 (3) | 0.010 (2) | −0.020 (3) |
C11 | 0.031 (3) | 0.049 (3) | 0.032 (3) | 0.016 (2) | 0.018 (2) | 0.005 (3) |
C12 | 0.048 (3) | 0.058 (3) | 0.048 (4) | −0.007 (3) | 0.024 (3) | 0.002 (3) |
C13 | 0.044 (4) | 0.056 (4) | 0.066 (5) | −0.014 (3) | 0.014 (4) | −0.010 (4) |
C14 | 0.0283 (19) | 0.030 (3) | 0.0235 (17) | 0.001 (3) | 0.0083 (15) | −0.004 (3) |
C15 | 0.0245 (18) | 0.022 (3) | 0.0281 (16) | 0.001 (2) | 0.0110 (14) | −0.004 (2) |
C16 | 0.0214 (16) | 0.021 (3) | 0.0282 (15) | 0.002 (2) | 0.0106 (13) | −0.003 (2) |
C17 | 0.0230 (16) | 0.017 (3) | 0.0243 (14) | 0.0040 (19) | 0.0084 (12) | 0.0019 (17) |
C18 | 0.0267 (17) | 0.025 (3) | 0.0336 (16) | 0.004 (2) | 0.0128 (14) | 0.002 (2) |
C19 | 0.0247 (18) | 0.035 (4) | 0.0331 (18) | 0.002 (3) | 0.0071 (15) | 0.000 (3) |
C20 | 0.032 (2) | 0.032 (3) | 0.0252 (17) | 0.001 (3) | 0.0074 (16) | −0.002 (3) |
Cl1A | 0.0236 (5) | 0.053 (6) | 0.0403 (5) | 0.0055 (13) | 0.0156 (4) | 0.0047 (14) |
O1A | 0.037 (2) | 0.062 (4) | 0.029 (2) | 0.000 (3) | 0.0123 (17) | 0.004 (2) |
O2A | 0.0313 (18) | 0.052 (3) | 0.034 (3) | 0.001 (2) | 0.020 (2) | 0.000 (2) |
O3A | 0.052 (3) | 0.087 (4) | 0.047 (3) | 0.003 (3) | 0.039 (2) | 0.005 (3) |
N1A | 0.0309 (10) | 0.0318 (10) | 0.0317 (10) | 0.0006 (4) | 0.0097 (5) | −0.0010 (4) |
N2A | 0.025 (2) | 0.068 (3) | 0.0295 (17) | 0.0047 (19) | 0.0131 (15) | −0.008 (2) |
C1A | 0.018 (3) | 0.035 (2) | 0.033 (2) | −0.0011 (16) | 0.0099 (19) | −0.0027 (17) |
C2A | 0.0267 (19) | 0.036 (3) | 0.0322 (18) | 0.000 (3) | 0.0094 (16) | 0.002 (2) |
C3A | 0.028 (2) | 0.040 (4) | 0.036 (2) | −0.001 (3) | 0.0118 (18) | −0.005 (3) |
C4A | 0.027 (3) | 0.050 (3) | 0.033 (3) | 0.007 (3) | 0.007 (2) | 0.004 (2) |
C5A | 0.038 (3) | 0.043 (3) | 0.048 (3) | 0.009 (3) | 0.014 (3) | 0.004 (2) |
C6A | 0.029 (3) | 0.033 (3) | 0.035 (3) | 0.002 (2) | 0.013 (3) | −0.007 (2) |
C7A | 0.039 (3) | 0.033 (2) | 0.044 (3) | 0.001 (2) | 0.015 (3) | −0.007 (3) |
C8A | 0.031 (3) | 0.040 (3) | 0.032 (3) | 0.005 (2) | 0.010 (2) | −0.007 (2) |
C9A | 0.048 (4) | 0.049 (4) | 0.048 (4) | −0.010 (3) | 0.012 (3) | −0.016 (3) |
C10A | 0.032 (3) | 0.080 (4) | 0.028 (3) | −0.015 (3) | 0.010 (2) | −0.020 (3) |
C11A | 0.031 (3) | 0.049 (3) | 0.032 (3) | 0.016 (2) | 0.018 (2) | 0.005 (3) |
C12A | 0.048 (3) | 0.058 (3) | 0.048 (4) | −0.007 (3) | 0.024 (3) | 0.002 (3) |
C13A | 0.044 (4) | 0.056 (4) | 0.066 (5) | −0.014 (3) | 0.014 (4) | −0.010 (4) |
C14A | 0.0283 (19) | 0.030 (3) | 0.0235 (17) | 0.001 (3) | 0.0083 (15) | −0.004 (3) |
C15A | 0.0245 (18) | 0.022 (3) | 0.0281 (16) | 0.001 (2) | 0.0110 (14) | −0.004 (2) |
C16A | 0.0214 (16) | 0.021 (3) | 0.0282 (15) | 0.002 (2) | 0.0106 (13) | −0.003 (2) |
C17A | 0.0230 (16) | 0.017 (3) | 0.0243 (14) | 0.0040 (19) | 0.0084 (12) | 0.0019 (17) |
C18A | 0.0267 (17) | 0.025 (3) | 0.0336 (16) | 0.004 (2) | 0.0128 (14) | 0.002 (2) |
C19A | 0.0247 (18) | 0.035 (4) | 0.0331 (18) | 0.002 (3) | 0.0071 (15) | 0.000 (3) |
C20A | 0.032 (2) | 0.032 (3) | 0.0252 (17) | 0.001 (3) | 0.0074 (16) | −0.002 (3) |
C21 | 0.031 (2) | 0.0236 (17) | 0.038 (2) | −0.0001 (14) | 0.0149 (16) | −0.0050 (14) |
C22 | 0.035 (2) | 0.0268 (18) | 0.043 (2) | −0.0036 (15) | 0.0227 (18) | −0.0041 (15) |
C23 | 0.044 (3) | 0.039 (3) | 0.038 (3) | −0.005 (2) | 0.013 (2) | −0.010 (3) |
C24 | 0.041 (3) | 0.064 (5) | 0.065 (5) | −0.004 (4) | 0.008 (4) | −0.025 (4) |
C23A | 0.044 (3) | 0.039 (3) | 0.038 (3) | −0.005 (2) | 0.013 (2) | −0.010 (3) |
C24A | 0.041 (3) | 0.064 (5) | 0.065 (5) | −0.004 (4) | 0.008 (4) | −0.025 (4) |
C25 | 0.027 (2) | 0.0231 (18) | 0.040 (2) | −0.0057 (14) | 0.0179 (16) | −0.0044 (14) |
C26 | 0.033 (2) | 0.033 (2) | 0.040 (2) | −0.0060 (17) | 0.0172 (18) | −0.0073 (16) |
C27 | 0.055 (3) | 0.075 (4) | 0.038 (2) | −0.025 (3) | 0.025 (2) | −0.018 (2) |
C28 | 0.079 (4) | 0.083 (4) | 0.057 (3) | −0.031 (3) | 0.049 (3) | −0.029 (3) |
Geometric parameters (Å, º) top
S1—O5 | 1.421 (3) | N1A—C1A | 1.414 (7) |
S1—O4 | 1.424 (3) | N1A—N2A | 1.418 (7) |
S1—N3 | 1.613 (3) | N1A—C8A | 1.535 (7) |
S1—C17 | 1.784 (3) | N2A—C14A | 1.339 (7) |
S1—C17A | 1.789 (3) | N2A—C10A | 1.538 (7) |
O6—C22 | 1.213 (5) | C1A—C2A | 1.382 (7) |
O7—C22 | 1.324 (5) | C1A—C6A | 1.388 (7) |
O7—C23A | 1.462 (6) | C2A—C3A | 1.397 (7) |
O7—C23 | 1.462 (6) | C2A—H2A | 0.9500 |
O8—C26 | 1.184 (5) | C3A—C4A | 1.432 (12) |
O9—C26 | 1.331 (5) | C3A—H3A | 0.9500 |
O9—C27 | 1.454 (6) | C4A—C5A | 1.363 (12) |
N3—C25 | 1.457 (5) | C4A—H4A | 0.9500 |
N3—C21 | 1.463 (5) | C5A—C6A | 1.355 (11) |
Cl1—C18 | 1.735 (3) | C5A—H5A | 0.9500 |
O1—C14 | 1.223 (7) | C6A—C7A | 1.510 (10) |
O2—C11 | 1.361 (9) | C7A—C8A | 1.520 (11) |
O2—C12 | 1.463 (10) | C7A—H7C | 0.9900 |
O3—C11 | 1.233 (7) | C7A—H7D | 0.9900 |
N1—N2 | 1.403 (6) | C8A—C9A | 1.503 (10) |
N1—C1 | 1.410 (6) | C8A—H8A | 1.0000 |
N1—C8 | 1.517 (7) | C9A—H9D | 0.9800 |
N2—C14 | 1.344 (7) | C9A—H9E | 0.9800 |
N2—C10 | 1.518 (7) | C9A—H9F | 0.9800 |
C1—C2 | 1.384 (7) | C10A—C11A | 1.433 (11) |
C1—C6 | 1.388 (7) | C10A—H10C | 0.9900 |
C2—C3 | 1.395 (7) | C10A—H10D | 0.9900 |
C2—H2 | 0.9500 | C12A—C13A | 1.475 (12) |
C3—C4 | 1.429 (11) | C12A—H12C | 0.9900 |
C3—H3 | 0.9500 | C12A—H12D | 0.9900 |
C4—C5 | 1.364 (12) | C13A—H13D | 0.9800 |
C4—H4 | 0.9500 | C13A—H13E | 0.9800 |
C5—C6 | 1.358 (11) | C13A—H13F | 0.9800 |
C5—H5 | 0.9500 | C14A—C15A | 1.520 (5) |
C6—C7 | 1.508 (10) | C15A—C16A | 1.3900 |
C7—C8 | 1.522 (11) | C15A—C20A | 1.3900 |
C7—H7A | 0.9900 | C16A—C17A | 1.3900 |
C7—H7B | 0.9900 | C16A—H16A | 0.9500 |
C8—C9 | 1.505 (10) | C17A—C18A | 1.3900 |
C8—H8 | 1.0000 | C18A—C19A | 1.3900 |
C9—H9A | 0.9800 | C19A—C20A | 1.3900 |
C9—H9B | 0.9800 | C19A—H19A | 0.9500 |
C9—H9C | 0.9800 | C20A—H20A | 0.9500 |
C10—C11 | 1.431 (11) | C21—C22 | 1.517 (5) |
C10—H10A | 0.9900 | C21—H21A | 0.9900 |
C10—H10B | 0.9900 | C21—H21B | 0.9900 |
C12—C13 | 1.478 (12) | C23—C24 | 1.526 (11) |
C12—H12A | 0.9900 | C23—H23A | 0.9900 |
C12—H12B | 0.9900 | C23—H23B | 0.9900 |
C13—H13A | 0.9800 | C24—H24A | 0.9800 |
C13—H13B | 0.9800 | C24—H24B | 0.9800 |
C13—H13C | 0.9800 | C24—H24C | 0.9800 |
C14—C15 | 1.515 (5) | C23A—C24A | 1.525 (11) |
C15—C16 | 1.3900 | C23A—H23C | 0.9900 |
C15—C20 | 1.3900 | C23A—H23D | 0.9900 |
C16—C17 | 1.3900 | C24A—H24D | 0.9800 |
C16—H16 | 0.9500 | C24A—H24E | 0.9800 |
C17—C18 | 1.3900 | C24A—H24F | 0.9800 |
C18—C19 | 1.3900 | C25—C26 | 1.508 (6) |
C19—C20 | 1.3900 | C25—H25A | 0.9900 |
C19—H19 | 0.9500 | C25—H25B | 0.9900 |
C20—H20 | 0.9500 | C27—C28 | 1.505 (7) |
Cl1A—C18A | 1.735 (3) | C27—H27A | 0.9900 |
O1A—C14A | 1.221 (7) | C27—H27B | 0.9900 |
O2A—C11A | 1.357 (9) | C28—H28A | 0.9800 |
O2A—C12A | 1.461 (10) | C28—H28B | 0.9800 |
O3A—C11A | 1.211 (7) | C28—H28C | 0.9800 |
| | | |
O5—S1—O4 | 119.78 (18) | C6A—C5A—H5A | 120.4 |
O5—S1—N3 | 107.34 (17) | C4A—C5A—H5A | 120.4 |
O4—S1—N3 | 109.32 (18) | C5A—C6A—C1A | 120.3 (7) |
O5—S1—C17 | 112.6 (2) | C5A—C6A—C7A | 130.4 (7) |
O4—S1—C17 | 104.8 (2) | C1A—C6A—C7A | 109.1 (6) |
N3—S1—C17 | 101.4 (3) | C6A—C7A—C8A | 103.2 (5) |
O5—S1—C17A | 105.0 (3) | C6A—C7A—H7C | 111.1 |
O4—S1—C17A | 105.4 (2) | C8A—C7A—H7C | 111.1 |
N3—S1—C17A | 109.7 (3) | C6A—C7A—H7D | 111.1 |
C22—O7—C23A | 117.9 (7) | C8A—C7A—H7D | 111.1 |
C22—O7—C23 | 116.5 (6) | H7C—C7A—H7D | 109.1 |
C26—O9—C27 | 116.2 (3) | C9A—C8A—C7A | 118.0 (7) |
C25—N3—C21 | 119.3 (3) | C9A—C8A—N1A | 109.3 (6) |
C25—N3—S1 | 121.8 (3) | C7A—C8A—N1A | 100.5 (5) |
C21—N3—S1 | 118.7 (2) | C9A—C8A—H8A | 109.5 |
C11—O2—C12 | 119.0 (6) | C7A—C8A—H8A | 109.5 |
N2—N1—C1 | 118.0 (4) | N1A—C8A—H8A | 109.5 |
N2—N1—C8 | 121.5 (5) | C8A—C9A—H9D | 109.5 |
C1—N1—C8 | 107.6 (5) | C8A—C9A—H9E | 109.5 |
C14—N2—N1 | 119.6 (5) | H9D—C9A—H9E | 109.5 |
C14—N2—C10 | 116.8 (5) | C8A—C9A—H9F | 109.5 |
N1—N2—C10 | 123.5 (5) | H9D—C9A—H9F | 109.5 |
C2—C1—C6 | 122.3 (5) | H9E—C9A—H9F | 109.5 |
C2—C1—N1 | 127.6 (4) | C11A—C10A—N2A | 111.1 (6) |
C6—C1—N1 | 110.0 (5) | C11A—C10A—H10C | 109.4 |
C1—C2—C3 | 117.6 (6) | N2A—C10A—H10C | 109.4 |
C1—C2—H2 | 121.2 | C11A—C10A—H10D | 109.4 |
C3—C2—H2 | 121.2 | N2A—C10A—H10D | 109.4 |
C2—C3—C4 | 118.5 (7) | H10C—C10A—H10D | 108.0 |
C2—C3—H3 | 120.7 | O3A—C11A—O2A | 123.3 (9) |
C4—C3—H3 | 120.7 | O3A—C11A—C10A | 124.2 (9) |
C5—C4—C3 | 122.1 (6) | O2A—C11A—C10A | 110.7 (5) |
C5—C4—H4 | 118.9 | O2A—C12A—C13A | 107.1 (7) |
C3—C4—H4 | 118.9 | O2A—C12A—H12C | 110.3 |
C6—C5—C4 | 118.6 (7) | C13A—C12A—H12C | 110.3 |
C6—C5—H5 | 120.7 | O2A—C12A—H12D | 110.3 |
C4—C5—H5 | 120.7 | C13A—C12A—H12D | 110.3 |
C5—C6—C1 | 120.8 (7) | H12C—C12A—H12D | 108.6 |
C5—C6—C7 | 129.8 (6) | C12A—C13A—H13D | 109.5 |
C1—C6—C7 | 109.4 (6) | C12A—C13A—H13E | 109.5 |
C6—C7—C8 | 103.8 (5) | H13D—C13A—H13E | 109.5 |
C6—C7—H7A | 111.0 | C12A—C13A—H13F | 109.5 |
C8—C7—H7A | 111.0 | H13D—C13A—H13F | 109.5 |
C6—C7—H7B | 111.0 | H13E—C13A—H13F | 109.5 |
C8—C7—H7B | 111.0 | O1A—C14A—N2A | 123.3 (5) |
H7A—C7—H7B | 109.0 | O1A—C14A—C15A | 120.4 (6) |
C9—C8—N1 | 111.7 (6) | N2A—C14A—C15A | 116.1 (5) |
C9—C8—C7 | 116.8 (7) | C16A—C15A—C20A | 120.0 |
N1—C8—C7 | 102.8 (5) | C16A—C15A—C14A | 120.7 (3) |
C9—C8—H8 | 108.4 | C20A—C15A—C14A | 119.2 (3) |
N1—C8—H8 | 108.4 | C15A—C16A—C17A | 120.0 |
C7—C8—H8 | 108.4 | C15A—C16A—H16A | 120.0 |
C8—C9—H9A | 109.5 | C17A—C16A—H16A | 120.0 |
C8—C9—H9B | 109.5 | C16A—C17A—C18A | 120.0 |
H9A—C9—H9B | 109.5 | C16A—C17A—S1 | 115.3 (3) |
C8—C9—H9C | 109.5 | C18A—C17A—S1 | 124.6 (3) |
H9A—C9—H9C | 109.5 | C19A—C18A—C17A | 120.0 |
H9B—C9—H9C | 109.5 | C19A—C18A—Cl1A | 117.7 (3) |
C11—C10—N2 | 124.7 (7) | C17A—C18A—Cl1A | 122.3 (3) |
C11—C10—H10A | 106.2 | C18A—C19A—C20A | 120.0 |
N2—C10—H10A | 106.2 | C18A—C19A—H19A | 120.0 |
C11—C10—H10B | 106.2 | C20A—C19A—H19A | 120.0 |
N2—C10—H10B | 106.2 | C19A—C20A—C15A | 120.0 |
H10A—C10—H10B | 106.4 | C19A—C20A—H20A | 120.0 |
O3—C11—O2 | 118.3 (7) | C15A—C20A—H20A | 120.0 |
O3—C11—C10 | 125.2 (8) | N3—C21—C22 | 115.5 (3) |
O2—C11—C10 | 114.5 (5) | N3—C21—H21A | 108.4 |
O2—C12—C13 | 107.3 (7) | C22—C21—H21A | 108.4 |
O2—C12—H12A | 110.3 | N3—C21—H21B | 108.4 |
C13—C12—H12A | 110.3 | C22—C21—H21B | 108.4 |
O2—C12—H12B | 110.3 | H21A—C21—H21B | 107.5 |
C13—C12—H12B | 110.3 | O6—C22—O7 | 125.1 (4) |
H12A—C12—H12B | 108.5 | O6—C22—C21 | 121.4 (4) |
C12—C13—H13A | 109.5 | O7—C22—C21 | 113.5 (3) |
C12—C13—H13B | 109.5 | O7—C23—C24 | 108.4 (8) |
H13A—C13—H13B | 109.5 | O7—C23—H23A | 110.0 |
C12—C13—H13C | 109.5 | C24—C23—H23A | 110.0 |
H13A—C13—H13C | 109.5 | O7—C23—H23B | 110.0 |
H13B—C13—H13C | 109.5 | C24—C23—H23B | 110.0 |
O1—C14—N2 | 119.5 (5) | H23A—C23—H23B | 108.4 |
O1—C14—C15 | 119.3 (5) | C23—C24—H24A | 109.5 |
N2—C14—C15 | 120.8 (5) | C23—C24—H24B | 109.5 |
C16—C15—C20 | 120.0 | H24A—C24—H24B | 109.5 |
C16—C15—C14 | 122.1 (3) | C23—C24—H24C | 109.5 |
C20—C15—C14 | 117.9 (3) | H24A—C24—H24C | 109.5 |
C17—C16—C15 | 120.0 | H24B—C24—H24C | 109.5 |
C17—C16—H16 | 120.0 | O7—C23A—C24A | 102.2 (8) |
C15—C16—H16 | 120.0 | O7—C23A—H23C | 111.3 |
C16—C17—C18 | 120.0 | C24A—C23A—H23C | 111.3 |
C16—C17—S1 | 116.6 (3) | O7—C23A—H23D | 111.3 |
C18—C17—S1 | 123.4 (3) | C24A—C23A—H23D | 111.3 |
C17—C18—C19 | 120.0 | H23C—C23A—H23D | 109.2 |
C17—C18—Cl1 | 122.3 (2) | C23A—C24A—H24D | 109.5 |
C19—C18—Cl1 | 117.7 (2) | C23A—C24A—H24E | 109.5 |
C20—C19—C18 | 120.0 | H24D—C24A—H24E | 109.5 |
C20—C19—H19 | 120.0 | C23A—C24A—H24F | 109.5 |
C18—C19—H19 | 120.0 | H24D—C24A—H24F | 109.5 |
C19—C20—C15 | 120.0 | H24E—C24A—H24F | 109.5 |
C19—C20—H20 | 120.0 | N3—C25—C26 | 112.3 (3) |
C15—C20—H20 | 120.0 | N3—C25—H25A | 109.1 |
C11A—O2A—C12A | 117.3 (7) | C26—C25—H25A | 109.1 |
C1A—N1A—N2A | 115.3 (5) | N3—C25—H25B | 109.1 |
C1A—N1A—C8A | 105.9 (5) | C26—C25—H25B | 109.1 |
N2A—N1A—C8A | 112.7 (5) | H25A—C25—H25B | 107.9 |
C14A—N2A—N1A | 121.3 (5) | O8—C26—O9 | 124.6 (4) |
C14A—N2A—C10A | 118.6 (5) | O8—C26—C25 | 125.6 (4) |
N1A—N2A—C10A | 110.5 (5) | O9—C26—C25 | 109.7 (3) |
C2A—C1A—C6A | 122.2 (6) | O9—C27—C28 | 106.9 (4) |
C2A—C1A—N1A | 128.4 (5) | O9—C27—H27A | 110.3 |
C6A—C1A—N1A | 109.1 (5) | C28—C27—H27A | 110.3 |
C1A—C2A—C3A | 118.1 (6) | O9—C27—H27B | 110.3 |
C1A—C2A—H2A | 120.9 | C28—C27—H27B | 110.3 |
C3A—C2A—H2A | 120.9 | H27A—C27—H27B | 108.6 |
C2A—C3A—C4A | 118.1 (7) | C27—C28—H28A | 109.5 |
C2A—C3A—H3A | 121.0 | C27—C28—H28B | 109.5 |
C4A—C3A—H3A | 121.0 | H28A—C28—H28B | 109.5 |
C5A—C4A—C3A | 121.9 (7) | C27—C28—H28C | 109.5 |
C5A—C4A—H4A | 119.1 | H28A—C28—H28C | 109.5 |
C3A—C4A—H4A | 119.1 | H28B—C28—H28C | 109.5 |
C6A—C5A—C4A | 119.3 (7) | | |
| | | |
O5—S1—N3—C25 | 3.4 (3) | C8A—N1A—C1A—C2A | 160 (2) |
O4—S1—N3—C25 | 134.7 (3) | N2A—N1A—C1A—C6A | −150.5 (9) |
C17—S1—N3—C25 | −114.9 (3) | C8A—N1A—C1A—C6A | −25.1 (12) |
C17A—S1—N3—C25 | −110.1 (4) | C6A—C1A—C2A—C3A | −3 (3) |
O5—S1—N3—C21 | −171.8 (3) | N1A—C1A—C2A—C3A | 171.0 (16) |
O4—S1—N3—C21 | −40.4 (3) | C1A—C2A—C3A—C4A | 2 (3) |
C17—S1—N3—C21 | 69.9 (4) | C2A—C3A—C4A—C5A | −2 (2) |
C17A—S1—N3—C21 | 74.7 (4) | C3A—C4A—C5A—C6A | 2.7 (18) |
C1—N1—N2—C14 | −125.3 (8) | C4A—C5A—C6A—C1A | −3.8 (17) |
C8—N1—N2—C14 | 98.0 (8) | C4A—C5A—C6A—C7A | −178.2 (10) |
C1—N1—N2—C10 | 56.6 (11) | C2A—C1A—C6A—C5A | 4 (2) |
C8—N1—N2—C10 | −80.0 (9) | N1A—C1A—C6A—C5A | −171.0 (10) |
N2—N1—C1—C2 | 24 (2) | C2A—C1A—C6A—C7A | 179.6 (19) |
C8—N1—C1—C2 | 166.5 (17) | N1A—C1A—C6A—C7A | 4.6 (14) |
N2—N1—C1—C6 | −159.4 (8) | C5A—C6A—C7A—C8A | −167.4 (10) |
C8—N1—C1—C6 | −17.3 (11) | C1A—C6A—C7A—C8A | 17.7 (12) |
C6—C1—C2—C3 | 2 (3) | C6A—C7A—C8A—C9A | −149.1 (7) |
N1—C1—C2—C3 | 177.6 (14) | C6A—C7A—C8A—N1A | −30.5 (8) |
C1—C2—C3—C4 | −2 (3) | C1A—N1A—C8A—C9A | 159.4 (9) |
C2—C3—C4—C5 | 1.9 (18) | N2A—N1A—C8A—C9A | −73.6 (8) |
C3—C4—C5—C6 | −1.7 (14) | C1A—N1A—C8A—C7A | 34.5 (8) |
C4—C5—C6—C1 | 1.5 (15) | N2A—N1A—C8A—C7A | 161.6 (6) |
C4—C5—C6—C7 | −178.3 (8) | C14A—N2A—C10A—C11A | 76.9 (10) |
C2—C1—C6—C5 | −2 (2) | N1A—N2A—C10A—C11A | −136.3 (7) |
N1—C1—C6—C5 | −178.1 (9) | C12A—O2A—C11A—O3A | −8.4 (14) |
C2—C1—C6—C7 | 178.3 (16) | C12A—O2A—C11A—C10A | −173.8 (9) |
N1—C1—C6—C7 | 1.8 (12) | N2A—C10A—C11A—O3A | −157.4 (9) |
C5—C6—C7—C8 | −166.1 (9) | N2A—C10A—C11A—O2A | 7.9 (11) |
C1—C6—C7—C8 | 14.1 (10) | C11A—O2A—C12A—C13A | −171.3 (10) |
N2—N1—C8—C9 | −68.4 (8) | N1A—N2A—C14A—O1A | −161.4 (9) |
C1—N1—C8—C9 | 151.1 (8) | C10A—N2A—C14A—O1A | −18.3 (13) |
N2—N1—C8—C7 | 165.6 (6) | N1A—N2A—C14A—C15A | 22.1 (11) |
C1—N1—C8—C7 | 25.1 (8) | C10A—N2A—C14A—C15A | 165.3 (7) |
C6—C7—C8—C9 | −145.6 (7) | O1A—C14A—C15A—C16A | −139.4 (8) |
C6—C7—C8—N1 | −22.9 (7) | N2A—C14A—C15A—C16A | 37.2 (10) |
C14—N2—C10—C11 | 54.6 (11) | O1A—C14A—C15A—C20A | 39.4 (11) |
N1—N2—C10—C11 | −127.3 (7) | N2A—C14A—C15A—C20A | −144.1 (6) |
C12—O2—C11—O3 | 1.3 (12) | C20A—C15A—C16A—C17A | 0.0 |
C12—O2—C11—C10 | 166.1 (8) | C14A—C15A—C16A—C17A | 178.7 (7) |
N2—C10—C11—O3 | −156.4 (8) | C15A—C16A—C17A—C18A | 0.0 |
N2—C10—C11—O2 | 40.0 (10) | C15A—C16A—C17A—S1 | 176.6 (6) |
C11—O2—C12—C13 | −164.7 (8) | O5—S1—C17A—C16A | 133.4 (4) |
N1—N2—C14—O1 | −162.5 (7) | O4—S1—C17A—C16A | 6.0 (5) |
C10—N2—C14—O1 | 15.7 (11) | N3—S1—C17A—C16A | −111.6 (4) |
N1—N2—C14—C15 | 24.8 (10) | O5—S1—C17A—C18A | −50.2 (5) |
C10—N2—C14—C15 | −157.0 (7) | O4—S1—C17A—C18A | −177.6 (4) |
O1—C14—C15—C16 | −143.7 (6) | N3—S1—C17A—C18A | 64.8 (5) |
N2—C14—C15—C16 | 29.1 (9) | C16A—C17A—C18A—C19A | 0.0 |
O1—C14—C15—C20 | 35.0 (9) | S1—C17A—C18A—C19A | −176.2 (6) |
N2—C14—C15—C20 | −152.3 (6) | C16A—C17A—C18A—Cl1A | 179.1 (10) |
C20—C15—C16—C17 | 0.0 | S1—C17A—C18A—Cl1A | 2.9 (10) |
C14—C15—C16—C17 | 178.6 (6) | C17A—C18A—C19A—C20A | 0.0 |
C15—C16—C17—C18 | 0.0 | Cl1A—C18A—C19A—C20A | −179.2 (10) |
C15—C16—C17—S1 | −179.3 (5) | C18A—C19A—C20A—C15A | 0.0 |
O5—S1—C17—C16 | 134.0 (3) | C16A—C15A—C20A—C19A | 0.0 |
O4—S1—C17—C16 | 2.2 (4) | C14A—C15A—C20A—C19A | −178.7 (7) |
N3—S1—C17—C16 | −111.6 (3) | C25—N3—C21—C22 | 78.8 (4) |
O5—S1—C17—C18 | −45.2 (4) | S1—N3—C21—C22 | −105.9 (4) |
O4—S1—C17—C18 | −177.1 (3) | C23A—O7—C22—O6 | −5.5 (10) |
N3—S1—C17—C18 | 69.2 (4) | C23—O7—C22—O6 | 9.4 (9) |
C16—C17—C18—C19 | 0.0 | C23A—O7—C22—C21 | 176.0 (9) |
S1—C17—C18—C19 | 179.2 (5) | C23—O7—C22—C21 | −169.2 (8) |
C16—C17—C18—Cl1 | 179.8 (8) | N3—C21—C22—O6 | −179.2 (4) |
S1—C17—C18—Cl1 | −1.0 (8) | N3—C21—C22—O7 | −0.5 (5) |
C17—C18—C19—C20 | 0.0 | C22—O7—C23—C24 | 177.1 (10) |
Cl1—C18—C19—C20 | −179.8 (8) | C22—O7—C23A—C24A | 131.8 (11) |
C18—C19—C20—C15 | 0.0 | C21—N3—C25—C26 | 74.6 (4) |
C16—C15—C20—C19 | 0.0 | S1—N3—C25—C26 | −100.5 (3) |
C14—C15—C20—C19 | −178.7 (6) | C27—O9—C26—O8 | 4.1 (7) |
C1A—N1A—N2A—C14A | −135.0 (9) | C27—O9—C26—C25 | −173.5 (4) |
C8A—N1A—N2A—C14A | 103.1 (8) | N3—C25—C26—O8 | 5.9 (6) |
C1A—N1A—N2A—C10A | 79.2 (10) | N3—C25—C26—O9 | −176.5 (3) |
C8A—N1A—N2A—C10A | −42.7 (8) | C26—O9—C27—C28 | 168.9 (4) |
N2A—N1A—C1A—C2A | 35 (2) | | |
Hydrogen-bond geometry (Å, º) topCg4 is the centroid of the major orientation of the C15–C20
benzene ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O2 | 0.95 | 2.37 | 3.198 (13) | 145 |
C4—H4···O9i | 0.95 | 2.48 | 3.262 (8) | 139 |
C10—H10A···Cl1i | 0.99 | 2.88 | 3.708 (11) | 141 |
C24—H24A···Cl1 | 0.98 | 2.86 | 3.51 (2) | 124 |
C25—H25A···O5ii | 0.99 | 2.41 | 3.100 (5) | 126 |
C27—H27B···Cg4ii | 0.99 | 2.92 | 3.742 (7) | 141 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, y−1/2, −z+1. |