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The title compound, C10H9NO3S, crystallizes with two molecules in the asymmetric unit. The crystal packing is stabilized by van der Waals forces.
Supporting information
CCDC reference: 289725
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.004 Å
- R factor = 0.040
- wR factor = 0.109
- Data-to-parameter ratio = 18.0
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for S2 - C17 .. 11.48 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for N2 - C17 .. 8.21 su
Alert level C
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C18
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C9
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C19
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.00
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 27.91
From the CIF: _reflns_number_total 4931
Count of symmetry unique reflns 2603
Completeness (_total/calc) 189.44%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 2328
Fraction of Friedel pairs measured 0.894
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 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
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
Please specify the role of each of the co-authors
for your paper.
1 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Methyl 2-oxo-2,3-dihydro-1,3-benzothiazole-3-acetate
top
Crystal data top
C10H9NO3S | F(000) = 464 |
Mr = 223.25 | Dx = 1.432 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 1967 reflections |
a = 4.7858 (3) Å | θ = 2.0–28.0° |
b = 12.4010 (7) Å | µ = 0.30 mm−1 |
c = 17.5319 (10) Å | T = 296 K |
β = 95.679 (5)° | Prism, pale yellow |
V = 1035.39 (11) Å3 | 0.53 × 0.35 × 0.17 mm |
Z = 4 | |
Data collection top
Stoe IPDS-II diffractometer | 4931 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 3875 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.070 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.9°, θmin = 2.0° |
ω scans | h = −6→6 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −16→16 |
Tmin = 0.858, Tmax = 0.951 | l = −22→22 |
17159 measured 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)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.109 | w = 1/[σ2(Fo2) + (0.0574P)2 + 0.0745P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
4931 reflections | Δρmax = 0.39 e Å−3 |
274 parameters | Δρmin = −0.39 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 2328 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.000 (1) |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The observed criterion of F2 > σ(F2)
is used only for calculating -R-factor-obs 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 | |
S1 | 0.65772 (14) | 0.50016 (5) | 0.17386 (4) | 0.0637 (2) | |
O1 | 0.9706 (4) | 0.38839 (19) | 0.08544 (11) | 0.0792 (7) | |
O2 | 0.4454 (4) | 0.16603 (17) | 0.07204 (12) | 0.0771 (7) | |
O3 | 0.7311 (4) | 0.02716 (14) | 0.10153 (12) | 0.0752 (6) | |
N1 | 0.7550 (4) | 0.29566 (16) | 0.17752 (11) | 0.0542 (6) | |
C1 | 0.4998 (5) | 0.42145 (19) | 0.23975 (13) | 0.0531 (7) | |
C2 | 0.3230 (5) | 0.4537 (2) | 0.29280 (15) | 0.0641 (8) | |
C3 | 0.2183 (6) | 0.3767 (3) | 0.33842 (15) | 0.0748 (9) | |
C4 | 0.2887 (6) | 0.2690 (3) | 0.33193 (15) | 0.0721 (9) | |
C5 | 0.4684 (5) | 0.2358 (2) | 0.27873 (14) | 0.0604 (8) | |
C6 | 0.5722 (4) | 0.31255 (18) | 0.23296 (12) | 0.0506 (6) | |
C7 | 0.8235 (5) | 0.3862 (2) | 0.13763 (14) | 0.0589 (8) | |
C8 | 0.8593 (5) | 0.1912 (2) | 0.15801 (15) | 0.0577 (7) | |
C9 | 0.6504 (4) | 0.12858 (19) | 0.10609 (13) | 0.0521 (7) | |
C10 | 0.5552 (8) | −0.0418 (3) | 0.0493 (2) | 0.0933 (13) | |
S2 | 0.45286 (19) | 0.87879 (8) | 0.45026 (6) | 0.0924 (3) | |
O4 | 0.4169 (9) | 0.9824 (2) | 0.3156 (2) | 0.1509 (18) | |
O5 | 0.3329 (5) | 0.71516 (19) | 0.21665 (11) | 0.0801 (8) | |
O6 | −0.0093 (5) | 0.7643 (2) | 0.12946 (11) | 0.0833 (8) | |
N2 | 0.1212 (6) | 0.8393 (2) | 0.32702 (15) | 0.0782 (9) | |
C11 | 0.2265 (5) | 0.7692 (2) | 0.44895 (15) | 0.0653 (8) | |
C12 | 0.1941 (6) | 0.6963 (3) | 0.50762 (16) | 0.0788 (12) | |
C13 | 0.0044 (7) | 0.6150 (3) | 0.4944 (2) | 0.0825 (10) | |
C14 | −0.1545 (6) | 0.6056 (3) | 0.42579 (18) | 0.0754 (10) | |
C15 | −0.1262 (6) | 0.6769 (2) | 0.36675 (16) | 0.0689 (9) | |
C16 | 0.0664 (5) | 0.7596 (2) | 0.37872 (14) | 0.0610 (8) | |
C17 | 0.3349 (9) | 0.9095 (3) | 0.3551 (3) | 0.1025 (15) | |
C18 | −0.0092 (8) | 0.8432 (3) | 0.2492 (2) | 0.0920 (14) | |
C19 | 0.1289 (6) | 0.7663 (2) | 0.19779 (15) | 0.0636 (8) | |
C20 | 0.1005 (8) | 0.6966 (3) | 0.07297 (18) | 0.0879 (13) | |
H2 | 0.27570 | 0.52590 | 0.29760 | 0.0770* | |
H3 | 0.09790 | 0.39710 | 0.37430 | 0.0900* | |
H4 | 0.21510 | 0.21830 | 0.36350 | 0.0860* | |
H5 | 0.51650 | 0.16350 | 0.27440 | 0.0720* | |
H8A | 0.90670 | 0.15040 | 0.20470 | 0.0690* | |
H8B | 1.02970 | 0.20050 | 0.13300 | 0.0690* | |
H10A | 0.36110 | −0.02550 | 0.05330 | 0.1400* | |
H10B | 0.59060 | −0.11600 | 0.06260 | 0.1400* | |
H10C | 0.59810 | −0.02940 | −0.00230 | 0.1400* | |
H12 | 0.29950 | 0.70300 | 0.55490 | 0.0950* | |
H13 | −0.01700 | 0.56490 | 0.53290 | 0.0990* | |
H14 | −0.28470 | 0.54990 | 0.41870 | 0.0900* | |
H15 | −0.23430 | 0.66950 | 0.32000 | 0.0830* | |
H18A | 0.00330 | 0.91600 | 0.22960 | 0.1110* | |
H18B | −0.20640 | 0.82490 | 0.24870 | 0.1110* | |
H20A | 0.29380 | 0.71450 | 0.06920 | 0.1320* | |
H20B | −0.00540 | 0.70770 | 0.02420 | 0.1320* | |
H20C | 0.08650 | 0.62240 | 0.08780 | 0.1320* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0710 (4) | 0.0503 (3) | 0.0689 (4) | 0.0021 (3) | 0.0027 (3) | 0.0024 (3) |
O1 | 0.0772 (12) | 0.0878 (14) | 0.0759 (12) | 0.0009 (11) | 0.0235 (10) | 0.0067 (11) |
O2 | 0.0589 (10) | 0.0802 (13) | 0.0866 (13) | 0.0192 (9) | −0.0204 (9) | −0.0188 (10) |
O3 | 0.0786 (11) | 0.0541 (10) | 0.0870 (12) | 0.0116 (8) | −0.0216 (10) | −0.0124 (9) |
N1 | 0.0544 (10) | 0.0509 (10) | 0.0567 (11) | 0.0033 (8) | 0.0026 (8) | −0.0059 (8) |
C1 | 0.0520 (12) | 0.0531 (12) | 0.0521 (12) | 0.0036 (9) | −0.0053 (9) | −0.0052 (9) |
C2 | 0.0611 (13) | 0.0697 (15) | 0.0603 (14) | 0.0095 (12) | −0.0004 (11) | −0.0133 (12) |
C3 | 0.0621 (14) | 0.104 (2) | 0.0582 (14) | 0.0073 (16) | 0.0057 (11) | −0.0071 (16) |
C4 | 0.0619 (14) | 0.097 (2) | 0.0561 (13) | −0.0073 (14) | −0.0002 (11) | 0.0118 (14) |
C5 | 0.0593 (13) | 0.0610 (14) | 0.0586 (13) | −0.0022 (10) | −0.0051 (11) | 0.0033 (11) |
C6 | 0.0460 (10) | 0.0544 (12) | 0.0491 (11) | 0.0027 (9) | −0.0060 (9) | −0.0021 (9) |
C7 | 0.0556 (12) | 0.0607 (14) | 0.0593 (13) | 0.0004 (11) | −0.0002 (10) | 0.0014 (12) |
C8 | 0.0500 (11) | 0.0568 (13) | 0.0641 (13) | 0.0095 (10) | −0.0053 (10) | −0.0099 (11) |
C9 | 0.0469 (10) | 0.0562 (12) | 0.0528 (12) | 0.0058 (9) | 0.0037 (9) | −0.0073 (10) |
C10 | 0.107 (3) | 0.0651 (18) | 0.102 (2) | −0.0024 (16) | −0.019 (2) | −0.0251 (16) |
S2 | 0.0888 (5) | 0.0844 (6) | 0.1059 (6) | −0.0170 (4) | 0.0191 (4) | −0.0384 (5) |
O4 | 0.211 (4) | 0.0722 (19) | 0.181 (3) | −0.015 (2) | 0.077 (3) | 0.0095 (19) |
O5 | 0.0798 (13) | 0.0881 (14) | 0.0704 (12) | 0.0258 (11) | −0.0031 (10) | −0.0079 (10) |
O6 | 0.0842 (13) | 0.0983 (15) | 0.0661 (11) | 0.0235 (12) | 0.0003 (10) | 0.0142 (11) |
N2 | 0.1027 (18) | 0.0590 (13) | 0.0744 (15) | 0.0103 (12) | 0.0166 (13) | −0.0042 (11) |
C11 | 0.0561 (12) | 0.0762 (17) | 0.0642 (14) | 0.0029 (12) | 0.0097 (11) | −0.0222 (13) |
C12 | 0.0710 (16) | 0.111 (3) | 0.0538 (14) | 0.0062 (17) | 0.0037 (12) | −0.0065 (16) |
C13 | 0.0809 (17) | 0.099 (2) | 0.0693 (17) | −0.0022 (17) | 0.0157 (14) | 0.0047 (16) |
C14 | 0.0697 (16) | 0.081 (2) | 0.0772 (18) | −0.0089 (14) | 0.0153 (13) | −0.0090 (15) |
C15 | 0.0669 (14) | 0.0736 (17) | 0.0647 (15) | 0.0023 (13) | −0.0015 (12) | −0.0161 (14) |
C16 | 0.0643 (13) | 0.0628 (14) | 0.0566 (13) | 0.0126 (11) | 0.0097 (10) | −0.0121 (12) |
C17 | 0.127 (3) | 0.0516 (17) | 0.138 (3) | 0.0049 (18) | 0.058 (3) | −0.0074 (19) |
C18 | 0.117 (3) | 0.080 (2) | 0.080 (2) | 0.0407 (19) | 0.0149 (18) | 0.0111 (16) |
C19 | 0.0702 (15) | 0.0589 (14) | 0.0619 (14) | 0.0095 (12) | 0.0074 (11) | 0.0123 (12) |
C20 | 0.096 (2) | 0.104 (3) | 0.0621 (16) | 0.004 (2) | 0.0006 (15) | −0.0055 (17) |
Geometric parameters (Å, º) top
S1—C1 | 1.741 (2) | C2—H2 | 0.9300 |
S1—C7 | 1.769 (3) | C3—H3 | 0.9300 |
S2—C11 | 1.737 (3) | C4—H4 | 0.9300 |
S2—C17 | 1.750 (5) | C5—H5 | 0.9300 |
O1—C7 | 1.209 (3) | C8—H8B | 0.9700 |
O2—C9 | 1.191 (3) | C8—H8A | 0.9700 |
O3—C10 | 1.458 (4) | C10—H10C | 0.9600 |
O3—C9 | 1.320 (3) | C10—H10A | 0.9600 |
O4—C17 | 1.227 (5) | C10—H10B | 0.9600 |
O5—C19 | 1.184 (4) | C11—C12 | 1.390 (4) |
O6—C19 | 1.310 (3) | C11—C16 | 1.389 (4) |
O6—C20 | 1.437 (4) | C12—C13 | 1.361 (5) |
N1—C8 | 1.442 (3) | C13—C14 | 1.363 (5) |
N1—C6 | 1.386 (3) | C14—C15 | 1.378 (4) |
N1—C7 | 1.379 (3) | C15—C16 | 1.381 (4) |
N2—C16 | 1.384 (4) | C18—C19 | 1.509 (5) |
N2—C17 | 1.395 (5) | C12—H12 | 0.9300 |
N2—C18 | 1.444 (4) | C13—H13 | 0.9300 |
C1—C2 | 1.377 (3) | C14—H14 | 0.9300 |
C1—C6 | 1.402 (3) | C15—H15 | 0.9300 |
C2—C3 | 1.372 (4) | C18—H18A | 0.9700 |
C3—C4 | 1.385 (5) | C18—H18B | 0.9700 |
C4—C5 | 1.392 (4) | C20—H20A | 0.9600 |
C5—C6 | 1.370 (3) | C20—H20B | 0.9600 |
C8—C9 | 1.500 (3) | C20—H20C | 0.9600 |
| | | |
S1···O5 | 3.212 (2) | C10···O1xi | 3.389 (4) |
S1···N1 | 2.578 (2) | C10···O6ix | 3.394 (4) |
S1···C2i | 3.675 (3) | C15···C19 | 3.494 (4) |
S2···C16i | 3.621 (3) | C15···S2iv | 3.613 (3) |
S2···N2 | 2.598 (3) | C16···O5 | 3.274 (3) |
S2···C15i | 3.613 (3) | C16···S2iv | 3.621 (3) |
S1···H10Cii | 3.1500 | C17···O5 | 3.420 (5) |
S1···H20Ci | 3.0700 | C19···C15 | 3.494 (4) |
S2···H13iii | 3.1400 | C20···C9ii | 3.568 (4) |
O1···C10ii | 3.389 (4) | C2···H14i | 3.0000 |
O2···C6 | 3.360 (3) | C4···H12xii | 2.7800 |
O2···C7 | 3.412 (3) | C5···H12xii | 3.0400 |
O2···N1 | 2.767 (3) | C5···H8Aiv | 3.0600 |
O2···C8iv | 3.328 (3) | C5···H8A | 2.7800 |
O4···C5v | 3.223 (4) | C8···H5 | 2.7600 |
O5···C16 | 3.274 (3) | C13···H4iii | 3.0800 |
O5···C17 | 3.420 (5) | C14···H3 | 3.0300 |
O5···N2 | 2.744 (3) | C15···H2 | 3.0200 |
O5···S1 | 3.212 (2) | C15···H18B | 2.7600 |
O6···C10vi | 3.394 (4) | C18···H15 | 2.7600 |
O1···H8B | 2.4800 | H2···C15 | 3.0200 |
O1···H10Cvii | 2.8300 | H2···O5 | 2.7700 |
O2···H10A | 2.4300 | H3···C14 | 3.0300 |
O2···H20Bviii | 2.6200 | H4···C13xiii | 3.0800 |
O2···H8Biv | 2.3900 | H5···C8 | 2.7600 |
O2···H10C | 2.8800 | H5···H8A | 2.3400 |
O3···H18Aix | 2.8400 | H5···O4x | 2.4200 |
O4···H5v | 2.4200 | H8A···C5 | 2.7800 |
O4···H18A | 2.5100 | H8A···H5 | 2.3400 |
O5···H2 | 2.7700 | H8A···C5i | 3.0600 |
O5···H15i | 2.6700 | H8B···O1 | 2.4800 |
O5···H18Bi | 2.6000 | H8B···O2i | 2.3900 |
O5···H20A | 2.5700 | H10A···O2 | 2.4300 |
O5···H20C | 2.7000 | H10B···O6ix | 2.6100 |
O6···H10Bvi | 2.6100 | H10B···H20Ax | 2.5500 |
N1···S1 | 2.578 (2) | H10C···S1xi | 3.1500 |
N1···O2 | 2.767 (3) | H10C···O1xiv | 2.8300 |
N2···O5 | 2.744 (3) | H10C···O2 | 2.8800 |
N2···S2 | 2.598 (3) | H12···C4xv | 2.7800 |
C1···C7iv | 3.567 (3) | H12···C5xv | 3.0400 |
C2···C7iv | 3.540 (4) | H13···S2xiii | 3.1400 |
C2···S1iv | 3.675 (3) | H14···C2iv | 3.0000 |
C3···C6iv | 3.533 (3) | H15···O5iv | 2.6700 |
C5···C9 | 3.494 (3) | H15···C18 | 2.7600 |
C5···O4x | 3.223 (4) | H15···H18B | 2.3100 |
C5···C8iv | 3.473 (3) | H18A···O3vi | 2.8400 |
C6···O2 | 3.360 (3) | H18A···O4 | 2.5100 |
C6···C3i | 3.533 (3) | H18B···O5iv | 2.6000 |
C7···C2i | 3.540 (4) | H18B···C15 | 2.7600 |
C7···C1i | 3.567 (3) | H18B···H15 | 2.3100 |
C7···O2 | 3.412 (3) | H20A···O5 | 2.5700 |
C8···C5i | 3.473 (3) | H20A···H10Bv | 2.5500 |
C8···O2i | 3.328 (3) | H20B···O2xvi | 2.6200 |
C9···C20xi | 3.568 (4) | H20C···S1iv | 3.0700 |
C9···C5 | 3.494 (3) | H20C···O5 | 2.7000 |
| | | |
C1—S1—C7 | 91.71 (11) | H10B—C10—H10C | 109.00 |
C11—S2—C17 | 90.90 (16) | O3—C10—H10A | 109.00 |
C9—O3—C10 | 116.3 (2) | O3—C10—H10B | 109.00 |
C19—O6—C20 | 117.1 (3) | O3—C10—H10C | 110.00 |
C6—N1—C7 | 115.51 (19) | H10A—C10—H10B | 109.00 |
C7—N1—C8 | 120.4 (2) | S2—C11—C12 | 127.9 (2) |
C6—N1—C8 | 124.0 (2) | S2—C11—C16 | 111.55 (19) |
C16—N2—C18 | 123.4 (3) | C12—C11—C16 | 120.5 (2) |
C16—N2—C17 | 113.2 (3) | C11—C12—C13 | 118.5 (3) |
C17—N2—C18 | 123.1 (3) | C12—C13—C14 | 121.2 (3) |
S1—C1—C2 | 128.41 (19) | C13—C14—C15 | 121.4 (3) |
C2—C1—C6 | 120.7 (2) | C14—C15—C16 | 118.4 (3) |
S1—C1—C6 | 110.89 (17) | N2—C16—C11 | 113.3 (2) |
C1—C2—C3 | 118.4 (2) | N2—C16—C15 | 126.7 (2) |
C2—C3—C4 | 121.2 (3) | C11—C16—C15 | 120.0 (2) |
C3—C4—C5 | 120.8 (3) | S2—C17—O4 | 127.4 (4) |
C4—C5—C6 | 118.1 (2) | S2—C17—N2 | 110.9 (3) |
C1—C6—C5 | 120.8 (2) | O4—C17—N2 | 121.7 (4) |
N1—C6—C1 | 112.54 (19) | N2—C18—C19 | 111.7 (3) |
N1—C6—C5 | 126.6 (2) | O5—C19—O6 | 125.0 (3) |
O1—C7—N1 | 126.0 (2) | O5—C19—C18 | 124.7 (3) |
S1—C7—N1 | 109.31 (17) | O6—C19—C18 | 110.3 (3) |
S1—C7—O1 | 124.7 (2) | C11—C12—H12 | 121.00 |
N1—C8—C9 | 112.55 (19) | C13—C12—H12 | 121.00 |
O2—C9—C8 | 124.7 (2) | C12—C13—H13 | 119.00 |
O3—C9—C8 | 110.39 (19) | C14—C13—H13 | 119.00 |
O2—C9—O3 | 124.9 (2) | C13—C14—H14 | 119.00 |
C3—C2—H2 | 121.00 | C15—C14—H14 | 119.00 |
C1—C2—H2 | 121.00 | C14—C15—H15 | 121.00 |
C4—C3—H3 | 119.00 | C16—C15—H15 | 121.00 |
C2—C3—H3 | 119.00 | N2—C18—H18A | 109.00 |
C3—C4—H4 | 120.00 | N2—C18—H18B | 109.00 |
C5—C4—H4 | 120.00 | C19—C18—H18A | 109.00 |
C4—C5—H5 | 121.00 | C19—C18—H18B | 109.00 |
C6—C5—H5 | 121.00 | H18A—C18—H18B | 108.00 |
C9—C8—H8A | 109.00 | O6—C20—H20A | 109.00 |
C9—C8—H8B | 109.00 | O6—C20—H20B | 109.00 |
N1—C8—H8B | 109.00 | O6—C20—H20C | 109.00 |
N1—C8—H8A | 109.00 | H20A—C20—H20B | 109.00 |
H8A—C8—H8B | 108.00 | H20A—C20—H20C | 109.00 |
H10A—C10—H10C | 110.00 | H20B—C20—H20C | 109.00 |
| | | |
C7—S1—C1—C2 | −179.7 (2) | C16—N2—C17—O4 | 177.3 (4) |
C7—S1—C1—C6 | −0.40 (18) | C18—N2—C16—C11 | 176.9 (3) |
C1—S1—C7—O1 | 178.4 (2) | C18—N2—C16—C15 | −3.8 (5) |
C1—S1—C7—N1 | −0.86 (18) | S1—C1—C2—C3 | 178.8 (2) |
C11—S2—C17—O4 | −178.3 (4) | C2—C1—C6—N1 | −179.1 (2) |
C11—S2—C17—N2 | 2.7 (3) | S1—C1—C6—C5 | −179.20 (18) |
C17—S2—C11—C16 | −1.1 (2) | C2—C1—C6—C5 | 0.2 (3) |
C17—S2—C11—C12 | 179.1 (3) | C6—C1—C2—C3 | −0.4 (4) |
C10—O3—C9—O2 | 1.3 (4) | S1—C1—C6—N1 | 1.6 (2) |
C10—O3—C9—C8 | −176.6 (2) | C1—C2—C3—C4 | 0.3 (4) |
C20—O6—C19—C18 | 178.5 (3) | C2—C3—C4—C5 | 0.0 (4) |
C20—O6—C19—O5 | −1.6 (4) | C3—C4—C5—C6 | −0.3 (4) |
C8—N1—C6—C1 | −179.0 (2) | C4—C5—C6—C1 | 0.2 (3) |
C6—N1—C8—C9 | 79.5 (3) | C4—C5—C6—N1 | 179.3 (2) |
C7—N1—C8—C9 | −97.0 (3) | N1—C8—C9—O2 | 14.1 (3) |
C8—N1—C7—S1 | 178.75 (17) | N1—C8—C9—O3 | −168.1 (2) |
C7—N1—C6—C5 | 178.5 (2) | S2—C11—C12—C13 | −179.6 (2) |
C8—N1—C6—C5 | 1.8 (3) | C16—C11—C12—C13 | 0.6 (4) |
C8—N1—C7—O1 | −0.5 (4) | S2—C11—C16—N2 | −0.7 (3) |
C7—N1—C6—C1 | −2.4 (3) | S2—C11—C16—C15 | 180.0 (2) |
C6—N1—C7—S1 | 2.0 (2) | C12—C11—C16—C15 | −0.2 (4) |
C6—N1—C7—O1 | −177.2 (2) | C12—C11—C16—N2 | 179.1 (3) |
C18—N2—C17—S2 | −177.7 (3) | C11—C12—C13—C14 | −1.1 (5) |
C16—N2—C17—S2 | −3.6 (4) | C12—C13—C14—C15 | 1.1 (5) |
C17—N2—C16—C11 | 2.8 (4) | C13—C14—C15—C16 | −0.6 (5) |
C17—N2—C16—C15 | −177.9 (3) | C14—C15—C16—C11 | 0.2 (4) |
C16—N2—C18—C19 | −79.5 (4) | C14—C15—C16—N2 | −179.0 (3) |
C17—N2—C18—C19 | 94.0 (4) | N2—C18—C19—O6 | 174.2 (3) |
C18—N2—C17—O4 | 3.2 (6) | N2—C18—C19—O5 | −5.7 (4) |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, y+1/2, −z; (iii) −x, y+1/2, −z+1; (iv) x−1, y, z; (v) x, y+1, z; (vi) x−1, y+1, z; (vii) −x+2, y+1/2, −z; (viii) −x, y−1/2, −z; (ix) x+1, y−1, z; (x) x, y−1, z; (xi) −x+1, y−1/2, −z; (xii) −x+1, y−1/2, −z+1; (xiii) −x, y−1/2, −z+1; (xiv) −x+2, y−1/2, −z; (xv) −x+1, y+1/2, −z+1; (xvi) −x, y+1/2, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O4x | 0.93 | 2.42 | 3.223 (4) | 144 |
C8—H8B···O1 | 0.97 | 2.48 | 2.831 (3) | 101 |
C8—H8B···O2i | 0.97 | 2.39 | 3.328 (3) | 163 |
C18—H18A···O4 | 0.97 | 2.51 | 2.833 (5) | 100 |
Symmetry codes: (i) x+1, y, z; (x) x, y−1, z. |
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