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The title compound, C17H19NO5S, crystallizes with two molecules per asymmetric unit; these do not exhibit the same pattern of hydrogen bonds. The indole part of the carbazole skeleton is almost planar, while the cyclohexenone ring is twisted.
Supporting information
CCDC reference: 643039
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.006 Å
- R factor = 0.070
- wR factor = 0.223
- Data-to-parameter ratio = 14.4
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.92
Alert level C
REFLT03_ALERT_3_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 74.23
From the CIF: _diffrn_reflns_theta_full 74.23
From the CIF: _reflns_number_total 6359
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 6882
Completeness (_total/calc) 92.40%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.92
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 4
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.11 Ratio
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.98 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.67 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.04 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for S1
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
9 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
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
7 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).
Ethyl
2-(9-methylsulfonyl-1-oxo-2,3,4,9-tetrahydro-1
H-carbazol-2-yl)acetate
top
Crystal data top
C17H19NO5S | Z = 4 |
Mr = 349.39 | F(000) = 736 |
Triclinic, P1 | Dx = 1.375 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54184 Å |
a = 8.651 (1) Å | Cell parameters from 16 reflections |
b = 12.320 (1) Å | θ = 20.7–42.0° |
c = 16.605 (2) Å | µ = 1.95 mm−1 |
α = 78.841 (7)° | T = 295 K |
β = 78.02 (1)° | Prism, colorless |
γ = 81.33 (1)° | 0.54 × 0.48 × 0.12 mm |
V = 1687.2 (3) Å3 | |
Data collection top
Enraf–Nonius TurboCAD-4 diffractometer | Rint = 0.054 |
non–profiled ω scans | θmax = 74.2°, θmin = 2.8° |
Absorption correction: ψ scan (North et al., 1968) | h = 0→10 |
Tmin = 0.429, Tmax = 0.788 | k = −15→15 |
6766 measured reflections | l = −20→20 |
6359 independent reflections | 3 standard reflections every 120 min |
4267 reflections with I > 2σ(I) | intensity decay: −7% |
Refinement top
Refinement on F2 | 3 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.070 | w = 1/[σ2(Fo2) + (0.1403P)2 + 0.2784P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.223 | (Δ/σ)max = 0.014 |
S = 1.03 | Δρmax = 0.64 e Å−3 |
6359 reflections | Δρmin = −0.47 e Å−3 |
443 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | −0.32112 (11) | 0.02271 (9) | 0.88393 (6) | 0.0434 (3) | |
S1' | 0.72350 (11) | 0.42416 (9) | 0.69110 (7) | 0.0470 (3) | |
N1 | −0.1843 (4) | −0.0002 (3) | 0.7999 (2) | 0.0413 (8) | |
C14 | 0.1727 (5) | 0.3106 (3) | 0.8554 (3) | 0.0461 (10) | |
O3 | 0.2368 (4) | 0.3163 (3) | 0.9212 (2) | 0.0567 (8) | |
C14' | 0.1878 (6) | 0.7465 (4) | 0.7855 (3) | 0.0560 (12) | |
O1' | 0.3871 (4) | 0.5457 (3) | 0.7743 (2) | 0.0592 (9) | |
N1' | 0.5615 (4) | 0.3864 (3) | 0.6658 (2) | 0.0395 (8) | |
O2' | 0.2897 (5) | 0.8020 (3) | 0.7435 (3) | 0.0779 (11) | |
O2 | 0.0608 (4) | 0.3736 (3) | 0.8362 (2) | 0.0655 (9) | |
O1 | 0.0021 (4) | 0.1133 (3) | 0.88955 (18) | 0.0588 (9) | |
O3' | 0.1320 (5) | 0.7485 (3) | 0.8651 (3) | 0.0787 (11) | |
C1' | 0.4511 (4) | 0.3429 (3) | 0.5639 (3) | 0.0402 (9) | |
C13 | 0.2620 (5) | 0.2210 (3) | 0.8099 (3) | 0.0435 (9) | |
H10 | 0.2987 | 0.1594 | 0.8501 | 0.052* | |
H11 | 0.3552 | 0.2491 | 0.7731 | 0.052* | |
C4 | −0.2003 (5) | −0.0615 (3) | 0.7391 (2) | 0.0393 (9) | |
C12 | 0.0327 (4) | 0.1153 (3) | 0.8145 (2) | 0.0375 (8) | |
C16' | 0.3364 (10) | 0.7343 (6) | 0.9435 (5) | 0.114 (3) | |
H14' | 0.2897 | 0.6786 | 0.9867 | 0.17* | |
H15' | 0.3968 | 0.7759 | 0.9665 | 0.17* | |
H16' | 0.4052 | 0.699 | 0.9004 | 0.17* | |
C11 | 0.1662 (5) | 0.1774 (3) | 0.7583 (3) | 0.0390 (9) | |
C2 | 0.0253 (4) | 0.0273 (3) | 0.6936 (2) | 0.0378 (8) | |
C15 | 0.1651 (7) | 0.4056 (5) | 0.9674 (4) | 0.0715 (15) | |
H12 | 0.0537 | 0.3975 | 0.9895 | 0.086* | |
H13 | 0.1718 | 0.477 | 0.9308 | 0.086* | |
C9 | 0.1784 (5) | 0.0651 (4) | 0.6447 (3) | 0.0514 (11) | |
H4 | 0.1571 | 0.1272 | 0.6011 | 0.062* | |
H5 | 0.2414 | 0.005 | 0.6185 | 0.062* | |
C10 | 0.2704 (5) | 0.1007 (4) | 0.7017 (3) | 0.0478 (10) | |
H2 | 0.3582 | 0.1389 | 0.668 | 0.057* | |
H3 | 0.3146 | 0.0351 | 0.7359 | 0.057* | |
C11' | 0.2072 (5) | 0.6197 (3) | 0.6800 (3) | 0.0431 (9) | |
C2' | 0.3595 (4) | 0.4402 (3) | 0.5921 (2) | 0.0397 (9) | |
C9' | 0.2079 (5) | 0.5013 (4) | 0.5690 (3) | 0.0477 (10) | |
H5' | 0.1463 | 0.4497 | 0.5558 | 0.057* | |
H4' | 0.2316 | 0.5574 | 0.5198 | 0.057* | |
C5' | 0.6757 (5) | 0.2129 (3) | 0.6020 (3) | 0.0468 (10) | |
H9' | 0.756 | 0.1902 | 0.6333 | 0.056* | |
C1 | −0.0704 (4) | −0.0454 (3) | 0.6731 (2) | 0.0378 (8) | |
C8' | 0.4345 (5) | 0.2808 (4) | 0.5049 (3) | 0.0467 (10) | |
H6' | 0.3566 | 0.3041 | 0.4722 | 0.056* | |
C6 | −0.2919 (6) | −0.1830 (4) | 0.6697 (3) | 0.0555 (12) | |
H8 | −0.3652 | −0.2302 | 0.6682 | 0.067* | |
C3' | 0.4253 (4) | 0.4649 (3) | 0.6531 (3) | 0.0383 (9) | |
C5 | −0.3127 (5) | −0.1296 (4) | 0.7378 (3) | 0.0518 (11) | |
H9 | −0.3994 | −0.1391 | 0.7812 | 0.062* | |
C4' | 0.5740 (4) | 0.3100 (3) | 0.6102 (3) | 0.0388 (9) | |
C3 | −0.0439 (4) | 0.0538 (3) | 0.7692 (2) | 0.0363 (8) | |
C10' | 0.1115 (5) | 0.5567 (4) | 0.6407 (3) | 0.0495 (10) | |
H3' | 0.0634 | 0.5 | 0.6836 | 0.059* | |
H2' | 0.0261 | 0.6082 | 0.6204 | 0.059* | |
C13' | 0.1054 (5) | 0.6711 (4) | 0.7511 (3) | 0.0525 (11) | |
H10' | 0.0699 | 0.6119 | 0.7959 | 0.063* | |
H11' | 0.0118 | 0.7135 | 0.7323 | 0.063* | |
C12' | 0.3490 (5) | 0.5439 (3) | 0.7082 (3) | 0.0415 (9) | |
C6' | 0.6520 (5) | 0.1510 (4) | 0.5451 (3) | 0.0527 (11) | |
H8' | 0.7165 | 0.0844 | 0.5394 | 0.063* | |
C15' | 0.2119 (8) | 0.8088 (5) | 0.9086 (4) | 0.0861 (19) | |
H13' | 0.2573 | 0.8706 | 0.87 | 0.103* | |
H12' | 0.1358 | 0.8387 | 0.9529 | 0.103* | |
C7' | 0.5345 (6) | 0.1851 (4) | 0.4960 (3) | 0.0554 (11) | |
H7' | 0.5245 | 0.1426 | 0.4572 | 0.066* | |
C7 | −0.1639 (6) | −0.1683 (4) | 0.6031 (3) | 0.0543 (11) | |
H7 | −0.1537 | −0.2048 | 0.5579 | 0.065* | |
C8 | −0.0531 (5) | −0.0998 (4) | 0.6045 (3) | 0.0484 (10) | |
H6 | 0.0324 | −0.0897 | 0.5605 | 0.058* | |
C16 | 0.2497 (10) | 0.4009 (6) | 1.0359 (5) | 0.113 (3) | |
H14 | 0.2404 | 0.3308 | 1.0726 | 0.169* | |
H15 | 0.2043 | 0.4604 | 1.0663 | 0.169* | |
H16 | 0.3599 | 0.4083 | 1.0136 | 0.169* | |
C17 | −0.2414 (6) | −0.0549 (5) | 0.9674 (3) | 0.0656 (14) | |
H19 | −0.1489 | −0.0241 | 0.9723 | 0.098* | |
H17 | −0.2121 | −0.1305 | 0.9584 | 0.098* | |
H18 | −0.319 | −0.0532 | 1.0179 | 0.098* | |
O4' | 0.7200 (4) | 0.5403 (3) | 0.6645 (2) | 0.0646 (10) | |
O4 | −0.3361 (4) | 0.1373 (3) | 0.8884 (2) | 0.0646 (9) | |
O5 | −0.4592 (3) | −0.0230 (3) | 0.8765 (2) | 0.0655 (10) | |
C17' | 0.6946 (6) | 0.3929 (5) | 0.7987 (3) | 0.0680 (14) | |
H19' | 0.6055 | 0.4409 | 0.8221 | 0.102* | |
H18' | 0.7882 | 0.4038 | 0.8172 | 0.102* | |
H17' | 0.6739 | 0.3168 | 0.8165 | 0.102* | |
O5' | 0.8559 (3) | 0.3518 (3) | 0.6568 (2) | 0.0645 (9) | |
H1 | 0.112 (5) | 0.241 (3) | 0.722 (3) | 0.046 (12)* | |
H1' | 0.251 (6) | 0.675 (3) | 0.632 (2) | 0.075 (16)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0320 (5) | 0.0489 (6) | 0.0467 (6) | −0.0072 (4) | 0.0032 (4) | −0.0112 (4) |
S1' | 0.0308 (5) | 0.0441 (6) | 0.0708 (7) | −0.0096 (4) | −0.0213 (5) | −0.0042 (5) |
N1 | 0.0324 (16) | 0.051 (2) | 0.0419 (18) | −0.0181 (14) | 0.0068 (13) | −0.0155 (15) |
C14 | 0.046 (2) | 0.042 (2) | 0.056 (3) | −0.0160 (19) | −0.016 (2) | −0.0056 (19) |
O3 | 0.063 (2) | 0.0498 (18) | 0.065 (2) | 0.0009 (15) | −0.0279 (17) | −0.0164 (15) |
C14' | 0.046 (3) | 0.047 (3) | 0.074 (3) | 0.004 (2) | −0.012 (2) | −0.013 (2) |
O1' | 0.0527 (19) | 0.065 (2) | 0.069 (2) | 0.0044 (15) | −0.0291 (16) | −0.0223 (17) |
N1' | 0.0257 (15) | 0.0382 (17) | 0.058 (2) | −0.0051 (13) | −0.0145 (14) | −0.0081 (15) |
O2' | 0.080 (3) | 0.062 (2) | 0.093 (3) | −0.029 (2) | −0.006 (2) | −0.012 (2) |
O2 | 0.062 (2) | 0.057 (2) | 0.086 (3) | 0.0086 (16) | −0.0359 (19) | −0.0196 (18) |
O1 | 0.062 (2) | 0.084 (2) | 0.0382 (16) | −0.0349 (17) | 0.0033 (14) | −0.0202 (15) |
O3' | 0.065 (2) | 0.099 (3) | 0.081 (3) | −0.015 (2) | −0.008 (2) | −0.037 (2) |
C1' | 0.0296 (18) | 0.043 (2) | 0.047 (2) | −0.0118 (16) | −0.0046 (16) | −0.0012 (17) |
C13 | 0.036 (2) | 0.047 (2) | 0.050 (2) | −0.0157 (17) | −0.0093 (18) | −0.0054 (18) |
C4 | 0.037 (2) | 0.040 (2) | 0.042 (2) | −0.0084 (16) | −0.0055 (16) | −0.0072 (17) |
C12 | 0.0334 (19) | 0.041 (2) | 0.039 (2) | −0.0100 (16) | −0.0013 (15) | −0.0089 (16) |
C16' | 0.144 (7) | 0.094 (5) | 0.132 (7) | −0.028 (5) | −0.068 (6) | −0.032 (5) |
C11 | 0.0348 (19) | 0.042 (2) | 0.040 (2) | −0.0149 (16) | −0.0045 (16) | −0.0021 (17) |
C2 | 0.036 (2) | 0.040 (2) | 0.037 (2) | −0.0101 (16) | −0.0025 (16) | −0.0062 (16) |
C15 | 0.082 (4) | 0.064 (3) | 0.079 (4) | 0.004 (3) | −0.028 (3) | −0.032 (3) |
C9 | 0.048 (2) | 0.066 (3) | 0.039 (2) | −0.023 (2) | 0.0067 (18) | −0.011 (2) |
C10 | 0.040 (2) | 0.054 (3) | 0.048 (2) | −0.0201 (19) | 0.0041 (18) | −0.0073 (19) |
C11' | 0.0333 (19) | 0.039 (2) | 0.057 (3) | −0.0032 (16) | −0.0141 (18) | −0.0031 (19) |
C2' | 0.0292 (18) | 0.044 (2) | 0.048 (2) | −0.0096 (16) | −0.0124 (16) | −0.0010 (18) |
C9' | 0.039 (2) | 0.049 (2) | 0.057 (3) | −0.0047 (18) | −0.0200 (19) | −0.003 (2) |
C5' | 0.0303 (19) | 0.049 (2) | 0.059 (3) | −0.0091 (17) | −0.0039 (18) | −0.005 (2) |
C1 | 0.0368 (19) | 0.039 (2) | 0.038 (2) | −0.0074 (16) | −0.0063 (16) | −0.0063 (16) |
C8' | 0.043 (2) | 0.056 (3) | 0.043 (2) | −0.0126 (19) | −0.0080 (18) | −0.0068 (19) |
C6 | 0.057 (3) | 0.056 (3) | 0.065 (3) | −0.018 (2) | −0.021 (2) | −0.018 (2) |
C3' | 0.0312 (18) | 0.035 (2) | 0.050 (2) | −0.0079 (15) | −0.0128 (16) | −0.0025 (17) |
C5 | 0.043 (2) | 0.052 (3) | 0.064 (3) | −0.0154 (19) | −0.006 (2) | −0.013 (2) |
C4' | 0.0290 (18) | 0.039 (2) | 0.049 (2) | −0.0112 (15) | −0.0072 (16) | −0.0018 (17) |
C3 | 0.0293 (17) | 0.040 (2) | 0.040 (2) | −0.0134 (15) | 0.0007 (15) | −0.0079 (16) |
C10' | 0.031 (2) | 0.050 (2) | 0.068 (3) | −0.0022 (18) | −0.0183 (19) | −0.006 (2) |
C13' | 0.042 (2) | 0.048 (3) | 0.066 (3) | −0.0034 (19) | −0.014 (2) | −0.006 (2) |
C12' | 0.035 (2) | 0.040 (2) | 0.054 (2) | −0.0104 (16) | −0.0140 (18) | −0.0070 (18) |
C6' | 0.042 (2) | 0.052 (3) | 0.060 (3) | −0.0059 (19) | 0.006 (2) | −0.014 (2) |
C15' | 0.086 (4) | 0.091 (5) | 0.096 (5) | −0.012 (4) | −0.014 (4) | −0.053 (4) |
C7' | 0.052 (3) | 0.061 (3) | 0.054 (3) | −0.013 (2) | 0.000 (2) | −0.019 (2) |
C7 | 0.066 (3) | 0.052 (3) | 0.054 (3) | −0.008 (2) | −0.020 (2) | −0.019 (2) |
C8 | 0.052 (2) | 0.051 (3) | 0.044 (2) | −0.006 (2) | −0.0081 (19) | −0.0146 (19) |
C16 | 0.142 (7) | 0.108 (6) | 0.116 (6) | 0.008 (5) | −0.066 (5) | −0.059 (5) |
C17 | 0.065 (3) | 0.076 (3) | 0.048 (3) | −0.014 (3) | −0.001 (2) | 0.003 (2) |
O4' | 0.0473 (18) | 0.0454 (18) | 0.105 (3) | −0.0197 (14) | −0.0301 (18) | 0.0059 (17) |
O4 | 0.063 (2) | 0.0507 (19) | 0.075 (2) | 0.0025 (16) | 0.0029 (18) | −0.0215 (17) |
O5 | 0.0317 (15) | 0.090 (3) | 0.079 (2) | −0.0266 (16) | 0.0095 (15) | −0.0294 (19) |
C17' | 0.063 (3) | 0.075 (4) | 0.072 (3) | −0.004 (3) | −0.037 (3) | −0.005 (3) |
O5' | 0.0321 (15) | 0.072 (2) | 0.097 (3) | −0.0034 (15) | −0.0214 (16) | −0.0257 (19) |
Geometric parameters (Å, º) top
S1—O4 | 1.413 (3) | C9—H4 | 0.97 |
S1—O5 | 1.432 (3) | C9—H5 | 0.97 |
S1—N1 | 1.671 (3) | C10—H2 | 0.97 |
S1—C17 | 1.731 (5) | C10—H3 | 0.97 |
S1'—O4' | 1.411 (3) | C11'—C13' | 1.504 (6) |
S1'—O5' | 1.432 (3) | C11'—C12' | 1.524 (5) |
S1'—N1' | 1.696 (3) | C11'—C10' | 1.526 (6) |
S1'—C17' | 1.726 (5) | C11'—H1' | 0.99 (2) |
N1—C4 | 1.411 (5) | C2'—C3' | 1.361 (5) |
N1—C3 | 1.426 (4) | C2'—C9' | 1.495 (5) |
C14—O2 | 1.203 (5) | C9'—C10' | 1.518 (6) |
C14—O3 | 1.342 (5) | C9'—H5' | 0.97 |
C14—C13 | 1.487 (6) | C9'—H4' | 0.97 |
O3—C15 | 1.452 (6) | C5'—C4' | 1.385 (6) |
C14'—O2' | 1.213 (6) | C5'—C6' | 1.386 (6) |
C14'—O3' | 1.314 (6) | C5'—H9' | 0.93 |
C14'—C13' | 1.507 (6) | C1—C8 | 1.401 (5) |
O1'—C12' | 1.216 (5) | C8'—C7' | 1.366 (6) |
N1'—C4' | 1.419 (5) | C8'—H6' | 0.93 |
N1'—C3' | 1.432 (5) | C6—C5 | 1.382 (6) |
O1—C12 | 1.215 (4) | C6—C7 | 1.399 (7) |
O3'—C15' | 1.457 (6) | C6—H8 | 0.93 |
C1'—C8' | 1.396 (6) | C3'—C12' | 1.456 (6) |
C1'—C4' | 1.404 (5) | C5—H9 | 0.93 |
C1'—C2' | 1.435 (6) | C10'—H3' | 0.97 |
C13—C11 | 1.522 (5) | C10'—H2' | 0.97 |
C13—H10 | 0.97 | C13'—H10' | 0.97 |
C13—H11 | 0.97 | C13'—H11' | 0.97 |
C4—C5 | 1.383 (6) | C6'—C7' | 1.399 (7) |
C4—C1 | 1.405 (5) | C6'—H8' | 0.93 |
C12—C3 | 1.470 (5) | C15'—H13' | 0.97 |
C12—C11 | 1.527 (5) | C15'—H12' | 0.97 |
C16'—C15' | 1.446 (9) | C7'—H7' | 0.93 |
C16'—H14' | 0.96 | C7—C8 | 1.376 (6) |
C16'—H15' | 0.96 | C7—H7 | 0.93 |
C16'—H16' | 0.96 | C8—H6 | 0.93 |
C11—C10 | 1.525 (6) | C16—H14 | 0.96 |
C11—H1 | 1.00 (4) | C16—H15 | 0.96 |
C2—C3 | 1.352 (5) | C16—H16 | 0.96 |
C2—C1 | 1.436 (5) | C17—H19 | 0.96 |
C2—C9 | 1.491 (5) | C17—H17 | 0.96 |
C15—C16 | 1.461 (8) | C17—H18 | 0.96 |
C15—H12 | 0.97 | C17'—H19' | 0.96 |
C15—H13 | 0.97 | C17'—H18' | 0.96 |
C9—C10 | 1.516 (6) | C17'—H17' | 0.96 |
| | | |
O4—S1—O5 | 118.0 (2) | C1'—C2'—C9' | 129.1 (4) |
O4—S1—N1 | 107.96 (18) | C2'—C9'—C10' | 110.3 (4) |
O5—S1—N1 | 105.94 (18) | C2'—C9'—H5' | 109.6 |
O4—S1—C17 | 109.9 (3) | C10'—C9'—H5' | 109.6 |
O5—S1—C17 | 109.6 (2) | C2'—C9'—H4' | 109.6 |
N1—S1—C17 | 104.5 (2) | C10'—C9'—H4' | 109.6 |
O4'—S1'—O5' | 119.4 (2) | H5'—C9'—H4' | 108.1 |
O4'—S1'—N1' | 106.60 (17) | C4'—C5'—C6' | 116.8 (4) |
O5'—S1'—N1' | 105.59 (18) | C4'—C5'—H9' | 121.6 |
O4'—S1'—C17' | 110.3 (3) | C6'—C5'—H9' | 121.6 |
O5'—S1'—C17' | 109.0 (2) | C8—C1—C4 | 119.6 (4) |
N1'—S1'—C17' | 104.8 (2) | C8—C1—C2 | 132.3 (4) |
C4—N1—C3 | 107.4 (3) | C4—C1—C2 | 108.1 (3) |
C4—N1—S1 | 125.8 (3) | C7'—C8'—C1' | 118.9 (4) |
C3—N1—S1 | 126.0 (3) | C7'—C8'—H6' | 120.5 |
O2—C14—O3 | 122.7 (4) | C1'—C8'—H6' | 120.5 |
O2—C14—C13 | 126.3 (4) | C5—C6—C7 | 122.0 (4) |
O3—C14—C13 | 111.0 (4) | C5—C6—H8 | 119 |
C14—O3—C15 | 115.8 (4) | C7—C6—H8 | 119 |
O2'—C14'—O3' | 124.1 (5) | C2'—C3'—N1' | 109.7 (3) |
O2'—C14'—C13' | 123.7 (5) | C2'—C3'—C12' | 124.2 (4) |
O3'—C14'—C13' | 112.1 (4) | N1'—C3'—C12' | 124.9 (3) |
C4'—N1'—C3' | 106.4 (3) | C6—C5—C4 | 117.7 (4) |
C4'—N1'—S1' | 122.3 (3) | C6—C5—H9 | 121.1 |
C3'—N1'—S1' | 121.6 (3) | C4—C5—H9 | 121.1 |
C14'—O3'—C15' | 118.0 (5) | C5'—C4'—C1' | 121.4 (4) |
C8'—C1'—C4' | 120.2 (4) | C5'—C4'—N1' | 130.2 (4) |
C8'—C1'—C2' | 132.2 (4) | C1'—C4'—N1' | 108.2 (3) |
C4'—C1'—C2' | 107.7 (4) | C2—C3—N1 | 109.5 (3) |
C14—C13—C11 | 114.2 (3) | C2—C3—C12 | 122.6 (3) |
C14—C13—H10 | 108.7 | N1—C3—C12 | 127.4 (3) |
C11—C13—H10 | 108.7 | C9'—C10'—C11' | 114.5 (3) |
C14—C13—H11 | 108.7 | C9'—C10'—H3' | 108.6 |
C11—C13—H11 | 108.7 | C11'—C10'—H3' | 108.6 |
H10—C13—H11 | 107.6 | C9'—C10'—H2' | 108.6 |
C5—C4—C1 | 121.4 (4) | C11'—C10'—H2' | 108.6 |
C5—C4—N1 | 131.3 (4) | H3'—C10'—H2' | 107.6 |
C1—C4—N1 | 107.2 (3) | C11'—C13'—C14' | 114.3 (4) |
O1—C12—C3 | 124.8 (3) | C11'—C13'—H10' | 108.7 |
O1—C12—C11 | 122.0 (4) | C14'—C13'—H10' | 108.7 |
C3—C12—C11 | 113.0 (3) | C11'—C13'—H11' | 108.7 |
C15'—C16'—H14' | 109.5 | C14'—C13'—H11' | 108.7 |
C15'—C16'—H15' | 109.5 | H10'—C13'—H11' | 107.6 |
H14'—C16'—H15' | 109.5 | O1'—C12'—C3' | 123.5 (4) |
C15'—C16'—H16' | 109.5 | O1'—C12'—C11' | 121.6 (4) |
H14'—C16'—H16' | 109.5 | C3'—C12'—C11' | 114.7 (3) |
H15'—C16'—H16' | 109.5 | C5'—C6'—C7' | 122.5 (4) |
C13—C11—C10 | 111.9 (3) | C5'—C6'—H8' | 118.8 |
C13—C11—C12 | 111.0 (3) | C7'—C6'—H8' | 118.8 |
C10—C11—C12 | 109.2 (3) | C16'—C15'—O3' | 109.6 (5) |
C13—C11—H1 | 111 (2) | C16'—C15'—H13' | 109.8 |
C10—C11—H1 | 108 (2) | O3'—C15'—H13' | 109.8 |
C12—C11—H1 | 106 (2) | C16'—C15'—H12' | 109.8 |
C3—C2—C1 | 107.8 (3) | O3'—C15'—H12' | 109.8 |
C3—C2—C9 | 124.0 (4) | H13'—C15'—H12' | 108.2 |
C1—C2—C9 | 128.1 (4) | C8'—C7'—C6' | 120.1 (4) |
O3—C15—C16 | 108.8 (5) | C8'—C7'—H7' | 120 |
O3—C15—H12 | 109.9 | C6'—C7'—H7' | 120 |
C16—C15—H12 | 109.9 | C8—C7—C6 | 119.9 (4) |
O3—C15—H13 | 109.9 | C8—C7—H7 | 120 |
C16—C15—H13 | 109.9 | C6—C7—H7 | 120 |
H12—C15—H13 | 108.3 | C7—C8—C1 | 119.3 (4) |
C2—C9—C10 | 110.1 (3) | C7—C8—H6 | 120.4 |
C2—C9—H4 | 109.6 | C1—C8—H6 | 120.4 |
C10—C9—H4 | 109.6 | C15—C16—H14 | 109.5 |
C2—C9—H5 | 109.6 | C15—C16—H15 | 109.5 |
C10—C9—H5 | 109.6 | H14—C16—H15 | 109.5 |
H4—C9—H5 | 108.2 | C15—C16—H16 | 109.5 |
C9—C10—C11 | 112.1 (4) | H14—C16—H16 | 109.5 |
C9—C10—H2 | 109.2 | H15—C16—H16 | 109.5 |
C11—C10—H2 | 109.2 | S1—C17—H19 | 109.5 |
C9—C10—H3 | 109.2 | S1—C17—H17 | 109.5 |
C11—C10—H3 | 109.2 | H19—C17—H17 | 109.5 |
H2—C10—H3 | 107.9 | S1—C17—H18 | 109.5 |
C13'—C11'—C12' | 110.9 (4) | H19—C17—H18 | 109.5 |
C13'—C11'—C10' | 111.8 (3) | H17—C17—H18 | 109.5 |
C12'—C11'—C10' | 110.7 (3) | S1'—C17'—H19' | 109.5 |
C13'—C11'—H1' | 114 (3) | S1'—C17'—H18' | 109.5 |
C12'—C11'—H1' | 106 (3) | H19'—C17'—H18' | 109.5 |
C10'—C11'—H1' | 103 (3) | S1'—C17'—H17' | 109.5 |
C3'—C2'—C1' | 108.0 (3) | H19'—C17'—H17' | 109.5 |
C3'—C2'—C9' | 122.6 (4) | H18'—C17'—H17' | 109.5 |
| | | |
O4—S1—N1—C4 | −132.5 (4) | C9'—C2'—C3'—C12' | 6.7 (6) |
O5—S1—N1—C4 | −5.2 (4) | C4'—N1'—C3'—C2' | −1.3 (4) |
C17—S1—N1—C4 | 110.6 (4) | S1'—N1'—C3'—C2' | 145.3 (3) |
O4—S1—N1—C3 | 35.9 (4) | C4'—N1'—C3'—C12' | 166.8 (4) |
O5—S1—N1—C3 | 163.1 (3) | S1'—N1'—C3'—C12' | −46.6 (5) |
C17—S1—N1—C3 | −81.1 (4) | C7—C6—C5—C4 | −1.1 (7) |
O2—C14—O3—C15 | −1.5 (7) | C1—C4—C5—C6 | 1.0 (7) |
C13—C14—O3—C15 | 176.3 (4) | N1—C4—C5—C6 | −177.1 (4) |
O4'—S1'—N1'—C4' | 119.0 (3) | C6'—C5'—C4'—C1' | 1.1 (6) |
O5'—S1'—N1'—C4' | −8.9 (4) | C6'—C5'—C4'—N1' | 175.6 (4) |
C17'—S1'—N1'—C4' | −124.0 (3) | C8'—C1'—C4'—C5' | −3.6 (6) |
O4'—S1'—N1'—C3' | −22.3 (4) | C2'—C1'—C4'—C5' | 174.7 (4) |
O5'—S1'—N1'—C3' | −150.2 (3) | C8'—C1'—C4'—N1' | −179.1 (3) |
C17'—S1'—N1'—C3' | 94.7 (4) | C2'—C1'—C4'—N1' | −0.8 (4) |
O2'—C14'—O3'—C15' | −8.8 (8) | C3'—N1'—C4'—C5' | −173.8 (4) |
C13'—C14'—O3'—C15' | 173.7 (4) | S1'—N1'—C4'—C5' | 39.9 (6) |
O2—C14—C13—C11 | −25.5 (6) | C3'—N1'—C4'—C1' | 1.3 (4) |
O3—C14—C13—C11 | 156.9 (4) | S1'—N1'—C4'—C1' | −145.1 (3) |
C3—N1—C4—C5 | 178.9 (4) | C1—C2—C3—N1 | 0.2 (5) |
S1—N1—C4—C5 | −11.0 (7) | C9—C2—C3—N1 | −177.2 (4) |
C3—N1—C4—C1 | 0.6 (4) | C1—C2—C3—C12 | 172.0 (3) |
S1—N1—C4—C1 | 170.7 (3) | C9—C2—C3—C12 | −5.4 (6) |
C14—C13—C11—C10 | 170.2 (3) | C4—N1—C3—C2 | −0.5 (5) |
C14—C13—C11—C12 | −67.5 (5) | S1—N1—C3—C2 | −170.6 (3) |
O1—C12—C11—C13 | 6.9 (6) | C4—N1—C3—C12 | −171.8 (4) |
C3—C12—C11—C13 | −169.1 (3) | S1—N1—C3—C12 | 18.1 (6) |
O1—C12—C11—C10 | 130.7 (4) | O1—C12—C3—C2 | −157.2 (4) |
C3—C12—C11—C10 | −45.3 (5) | C11—C12—C3—C2 | 18.7 (5) |
C14—O3—C15—C16 | −179.2 (5) | O1—C12—C3—N1 | 13.1 (7) |
C3—C2—C9—C10 | 19.5 (6) | C11—C12—C3—N1 | −171.1 (4) |
C1—C2—C9—C10 | −157.4 (4) | C2'—C9'—C10'—C11' | 46.3 (5) |
C2—C9—C10—C11 | −47.4 (5) | C13'—C11'—C10'—C9' | −179.2 (4) |
C13—C11—C10—C9 | −175.0 (3) | C12'—C11'—C10'—C9' | −55.0 (5) |
C12—C11—C10—C9 | 61.7 (5) | C12'—C11'—C13'—C14' | 63.3 (5) |
C8'—C1'—C2'—C3' | 178.1 (4) | C10'—C11'—C13'—C14' | −172.6 (4) |
C4'—C1'—C2'—C3' | 0.0 (4) | O2'—C14'—C13'—C11' | 31.8 (6) |
C8'—C1'—C2'—C9' | 4.4 (7) | O3'—C14'—C13'—C11' | −150.7 (4) |
C4'—C1'—C2'—C9' | −173.6 (4) | C2'—C3'—C12'—O1' | 160.9 (4) |
C3'—C2'—C9'—C10' | −22.0 (5) | N1'—C3'—C12'—O1' | −5.5 (6) |
C1'—C2'—C9'—C10' | 150.8 (4) | C2'—C3'—C12'—C11' | −14.5 (6) |
C5—C4—C1—C8 | −0.5 (6) | N1'—C3'—C12'—C11' | 179.1 (3) |
N1—C4—C1—C8 | 178.0 (4) | C13'—C11'—C12'—O1' | −13.8 (6) |
C5—C4—C1—C2 | −179.0 (4) | C10'—C11'—C12'—O1' | −138.4 (4) |
N1—C4—C1—C2 | −0.4 (4) | C13'—C11'—C12'—C3' | 161.7 (3) |
C3—C2—C1—C8 | −178.1 (4) | C10'—C11'—C12'—C3' | 37.1 (5) |
C9—C2—C1—C8 | −0.8 (7) | C4'—C5'—C6'—C7' | 1.7 (6) |
C3—C2—C1—C4 | 0.2 (5) | C14'—O3'—C15'—C16' | −90.0 (7) |
C9—C2—C1—C4 | 177.4 (4) | C1'—C8'—C7'—C6' | −0.4 (7) |
C4'—C1'—C8'—C7' | 3.1 (6) | C5'—C6'—C7'—C8' | −2.1 (7) |
C2'—C1'—C8'—C7' | −174.7 (4) | C5—C6—C7—C8 | 0.7 (7) |
C1'—C2'—C3'—N1' | 0.8 (4) | C6—C7—C8—C1 | −0.1 (7) |
C9'—C2'—C3'—N1' | 174.9 (4) | C4—C1—C8—C7 | 0.0 (6) |
C1'—C2'—C3'—C12' | −167.4 (4) | C2—C1—C8—C7 | 178.0 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H9···O5 | 0.93 | 2.27 | 2.845 (6) | 120 |
C5′—H9′···O5′ | 0.93 | 2.42 | 2.866 (6) | 109 |
C17—H19···O1 | 0.96 | 2.34 | 3.091 (7) | 134 |
C17′—H19′···O1′ | 0.96 | 2.32 | 3.075 (7) | 135 |
C17′—H17′···O4i | 0.96 | 2.31 | 3.237 (7) | 164 |
C17—H18···O5ii | 0.96 | 2.52 | 3.433 (6) | 159 |
C17′—H18′···O2i | 0.96 | 2.40 | 3.314 (7) | 158 |
Symmetry codes: (i) x+1, y, z; (ii) −x−1, −y, −z+2. |
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