The spectroscopically confused title compound, C13H18INO2S, wrongly assigned previously, has been crystallographically identified. The relative configuration is the (R*,S*) form and not the (R*,R*) type as previously reported.
Supporting information
CCDC reference: 293807
Key indicators
- Single-crystal X-ray study
- T = 93 K
- Mean (C-C) = 0.007 Å
- R factor = 0.046
- wR factor = 0.081
- Data-to-parameter ratio = 16.3
checkCIF/PLATON results
No syntax errors found
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 68.23
From the CIF: _reflns_number_total 2702
Count of symmetry unique reflns 1596
Completeness (_total/calc) 169.30%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1106
Fraction of Friedel pairs measured 0.693
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
0 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
0 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
Data collection: PROCESS-AUTO (Rigaku Corporation, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC & Rigaku Corporation, 2005); program(s) used to solve structure: SIR97 (Altomare, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: CrystalStructure.
Crystal data top
C13H18INO2S | F(000) = 752.00 |
Mr = 379.26 | Dx = 1.704 Mg m−3 |
Orthorhombic, P212121 | Cu Kα radiation, λ = 1.54187 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 16475 reflections |
a = 6.2297 (4) Å | θ = 3.6–68.2° |
b = 12.2538 (8) Å | µ = 18.30 mm−1 |
c = 19.3613 (13) Å | T = 93 K |
V = 1477.99 (17) Å3 | Needle, colorless |
Z = 4 | 0.15 × 0.03 × 0.02 mm |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 2426 reflections with F2 > 2.0σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.099 |
ω scans | θmax = 68.2° |
Absorption correction: multi-scan (Higashi, 1995) | h = −7→7 |
Tmin = 0.510, Tmax = 0.694 | k = −14→14 |
17233 measured reflections | l = −22→23 |
2702 independent reflections | |
Refinement top
Refinement on F2 | w = 1/[σ2(Fo2)] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.046 | (Δ/σ)max = 0.002 |
wR(F2) = 0.081 | Δρmax = 1.47 e Å−3 |
S = 1.04 | Δρmin = −0.75 e Å−3 |
2702 reflections | Absolute structure: Flack (1983), 1110 Friedel Pairs |
166 parameters | Absolute structure parameter: −0.014 (9) |
H-atom parameters constrained | |
Special details top
Refinement. Refinement using all reflections. The weighted R-factor(wR),
goodness of fit (S) and R-factor (gt) are based on F,
with F set to zero for negative F. The threshold expression of
F2 > 2.0 σ(F2) is used only for calculating R-factor
(gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I(8) | 0.23910 (6) | 0.22564 (3) | 0.93028 (2) | 0.03997 (15) | |
S(9) | 0.1133 (2) | 0.24333 (11) | 0.69763 (6) | 0.0276 (3) | |
O(10) | 0.2049 (6) | 0.1366 (2) | 0.70611 (17) | 0.0290 (10) | |
O(11) | −0.1149 (5) | 0.2558 (2) | 0.69029 (18) | 0.0301 (10) | |
N(1) | 0.1813 (6) | 0.3130 (3) | 0.7653 (2) | 0.0227 (11) | |
C(2) | 0.4134 (8) | 0.3052 (4) | 0.7896 (2) | 0.0244 (13) | |
C(3) | 0.4589 (9) | 0.4215 (4) | 0.8157 (2) | 0.0340 (16) | |
C(4) | 0.3087 (8) | 0.4927 (4) | 0.7735 (3) | 0.0357 (17) | |
C(5) | 0.1053 (8) | 0.4271 (4) | 0.7712 (2) | 0.0281 (14) | |
C(6) | 0.4465 (9) | 0.2137 (4) | 0.8408 (2) | 0.0336 (16) | |
C(7) | 0.6784 (8) | 0.2100 (4) | 0.8638 (2) | 0.0351 (16) | |
C(12) | 0.2348 (8) | 0.3038 (4) | 0.6248 (2) | 0.0236 (12) | |
C(13) | 0.4386 (9) | 0.2709 (4) | 0.6041 (2) | 0.0285 (15) | |
C(14) | 0.5356 (9) | 0.3218 (4) | 0.5486 (2) | 0.0287 (14) | |
C(15) | 0.4396 (10) | 0.4074 (4) | 0.5144 (2) | 0.0306 (15) | |
C(16) | 0.2344 (11) | 0.4404 (4) | 0.5364 (2) | 0.0321 (15) | |
C(17) | 0.1323 (8) | 0.3894 (4) | 0.5902 (2) | 0.0289 (15) | |
C(18) | 0.5475 (10) | 0.4634 (4) | 0.4541 (2) | 0.0422 (18) | |
H(2) | 0.5065 | 0.2911 | 0.7485 | 0.029* | |
H(3A) | 0.4271 | 0.4279 | 0.8657 | 0.041* | |
H(3B) | 0.6106 | 0.4420 | 0.8076 | 0.041* | |
H(4A) | 0.2850 | 0.5641 | 0.7962 | 0.043* | |
H(4B) | 0.3663 | 0.5051 | 0.7265 | 0.043* | |
H(5A) | 0.0200 | 0.4376 | 0.8138 | 0.034* | |
H(5B) | 0.0167 | 0.4477 | 0.7308 | 0.034* | |
H(6) | 0.4135 | 0.1434 | 0.8168 | 0.040* | |
H(7A) | 0.7037 | 0.1431 | 0.8903 | 0.053* | |
H(7B) | 0.7094 | 0.2736 | 0.8928 | 0.053* | |
H(7C) | 0.7723 | 0.2108 | 0.8232 | 0.053* | |
H(13) | 0.5105 | 0.2139 | 0.6279 | 0.034* | |
H(14) | 0.6724 | 0.2970 | 0.5336 | 0.034* | |
H(16) | 0.1651 | 0.4991 | 0.5134 | 0.039* | |
H(17) | −0.0072 | 0.4121 | 0.6039 | 0.035* | |
H(18A) | 0.5234 | 0.5423 | 0.4571 | 0.063* | |
H(18B) | 0.4869 | 0.4358 | 0.4107 | 0.063* | |
H(18C) | 0.7020 | 0.4484 | 0.4552 | 0.063* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I(8) | 0.0365 (3) | 0.0498 (3) | 0.0336 (2) | 0.0036 (2) | 0.0040 (2) | 0.00610 (16) |
S(9) | 0.0249 (10) | 0.0272 (8) | 0.0306 (8) | −0.0023 (7) | −0.0008 (7) | −0.0001 (6) |
O(10) | 0.034 (2) | 0.0200 (19) | 0.033 (2) | −0.0020 (19) | −0.002 (2) | 0.0003 (16) |
O(11) | 0.020 (2) | 0.036 (2) | 0.034 (2) | −0.0027 (18) | −0.001 (2) | 0.0019 (19) |
N(1) | 0.025 (3) | 0.022 (2) | 0.021 (2) | 0.002 (2) | −0.001 (2) | −0.002 (2) |
C(2) | 0.020 (3) | 0.031 (3) | 0.023 (3) | −0.005 (2) | −0.001 (2) | −0.002 (2) |
C(3) | 0.033 (4) | 0.029 (3) | 0.041 (3) | −0.005 (3) | −0.007 (3) | −0.000 (2) |
C(4) | 0.019 (4) | 0.031 (3) | 0.057 (4) | −0.007 (3) | −0.002 (3) | −0.004 (3) |
C(5) | 0.026 (4) | 0.028 (3) | 0.031 (3) | 0.005 (3) | −0.005 (2) | 0.003 (2) |
C(6) | 0.038 (4) | 0.035 (3) | 0.028 (3) | 0.014 (3) | 0.007 (3) | −0.004 (2) |
C(7) | 0.031 (4) | 0.041 (4) | 0.033 (3) | −0.002 (3) | 0.009 (3) | 0.004 (2) |
C(12) | 0.017 (3) | 0.029 (3) | 0.025 (2) | 0.005 (3) | −0.008 (2) | −0.003 (2) |
C(13) | 0.028 (4) | 0.028 (3) | 0.030 (3) | −0.002 (3) | −0.004 (2) | 0.005 (2) |
C(14) | 0.020 (3) | 0.032 (3) | 0.035 (3) | 0.004 (3) | 0.004 (3) | −0.008 (2) |
C(15) | 0.036 (4) | 0.029 (3) | 0.026 (3) | −0.001 (3) | −0.000 (3) | −0.004 (2) |
C(16) | 0.046 (4) | 0.023 (2) | 0.027 (3) | 0.009 (3) | −0.010 (3) | −0.001 (2) |
C(17) | 0.023 (3) | 0.036 (3) | 0.029 (3) | 0.006 (3) | −0.006 (2) | −0.001 (2) |
C(18) | 0.058 (5) | 0.033 (3) | 0.036 (4) | 0.005 (3) | 0.009 (3) | 0.002 (3) |
Geometric parameters (Å, º) top
I(8)—C(6) | 2.167 (5) | C(2)—H(2) | 1.000 |
S(9)—O(10) | 1.437 (3) | C(3)—H(3A) | 0.990 |
S(9)—O(11) | 1.437 (4) | C(3)—H(3B) | 0.990 |
S(9)—N(1) | 1.621 (4) | C(4)—H(4A) | 0.990 |
S(9)—C(12) | 1.763 (5) | C(4)—H(4B) | 0.990 |
N(1)—C(2) | 1.523 (6) | C(5)—H(5A) | 0.990 |
N(1)—C(5) | 1.481 (6) | C(5)—H(5B) | 0.990 |
C(2)—C(3) | 1.540 (7) | C(6)—H(6) | 1.000 |
C(2)—C(6) | 1.510 (7) | C(7)—H(7A) | 0.980 |
C(3)—C(4) | 1.518 (7) | C(7)—H(7B) | 0.980 |
C(4)—C(5) | 1.501 (7) | C(7)—H(7C) | 0.980 |
C(6)—C(7) | 1.513 (8) | C(13)—H(13) | 0.950 |
C(12)—C(13) | 1.391 (7) | C(14)—H(14) | 0.950 |
C(12)—C(17) | 1.400 (7) | C(16)—H(16) | 0.950 |
C(13)—C(14) | 1.381 (7) | C(17)—H(17) | 0.950 |
C(14)—C(15) | 1.377 (8) | C(18)—H(18A) | 0.980 |
C(15)—C(16) | 1.407 (9) | C(18)—H(18B) | 0.980 |
C(15)—C(18) | 1.513 (8) | C(18)—H(18C) | 0.980 |
C(16)—C(17) | 1.371 (7) | | |
| | | |
O(10)···C(3)i | 3.393 (6) | C(13)···H(14)iii | 3.248 |
O(10)···C(4)i | 3.528 (6) | C(13)···H(18C)iii | 3.273 |
O(10)···C(5)ii | 3.243 (6) | C(14)···H(14)iii | 3.126 |
O(10)···C(18)iii | 3.475 (6) | C(14)···H(17)vii | 3.238 |
O(11)···C(2)iv | 3.563 (6) | C(15)···H(7A)viii | 3.541 |
O(11)···C(4)ii | 3.514 (6) | C(15)···H(14)iii | 3.148 |
O(11)···C(13)iv | 3.249 (6) | C(16)···H(7A)viii | 2.887 |
O(11)···C(14)iv | 3.594 (6) | C(16)···H(14)iii | 3.231 |
I(8)···H(7A)iv | 3.570 | C(17)···H(7A)viii | 3.294 |
I(8)···H(7B)iv | 3.430 | C(17)···H(14)iv | 3.270 |
I(8)···H(7B)v | 3.430 | C(17)···H(14)iii | 3.320 |
I(8)···H(7C)iv | 3.576 | C(18)···H(5A)ix | 3.004 |
I(8)···H(18A)i | 3.463 | H(2)···H(4A)i | 3.190 |
I(8)···H(18A)vi | 3.321 | H(3A)···H(13)viii | 3.527 |
S(9)···H(4A)ii | 3.316 | H(3A)···H(16)vi | 3.051 |
S(9)···H(7C)iv | 3.253 | H(3A)···H(18A)vi | 3.338 |
S(9)···H(18B)iii | 3.136 | H(3A)···H(18B)vi | 3.194 |
O(10)···H(3B)i | 2.661 | H(3A)···H(18C)x | 3.262 |
O(10)···H(4A)ii | 3.179 | H(3B)···H(5A)vii | 2.554 |
O(10)···H(4A)i | 3.300 | H(3B)···H(5B)vii | 2.936 |
O(10)···H(4B)i | 3.382 | H(3B)···H(6)viii | 3.452 |
O(10)···H(5A)ii | 2.837 | H(3B)···H(18B)x | 3.538 |
O(10)···H(5B)ii | 2.959 | H(3B)···H(18C)x | 3.366 |
O(10)···H(18B)iii | 2.783 | H(4A)···H(6)viii | 3.043 |
O(10)···H(18C)iii | 3.292 | H(4A)···H(7C)viii | 2.951 |
O(11)···H(2)iv | 2.649 | H(4A)···H(13)viii | 2.674 |
O(11)···H(4A)ii | 2.591 | H(4A)···H(18B)vi | 2.790 |
O(11)···H(7C)iv | 2.724 | H(4B)···H(6)viii | 2.336 |
O(11)···H(13)iv | 2.677 | H(4B)···H(7A)viii | 2.858 |
O(11)···H(14)iv | 3.349 | H(4B)···H(7C)viii | 2.833 |
O(11)···H(18B)iii | 3.121 | H(5A)···H(7B)iv | 3.182 |
N(1)···H(7C)iv | 3.052 | H(5A)···H(7C)iv | 3.184 |
C(3)···H(5A)vii | 3.501 | H(5A)···H(18A)vi | 2.798 |
C(4)···H(6)viii | 3.076 | H(5A)···H(18B)vi | 2.436 |
C(4)···H(7C)viii | 3.303 | H(5A)···H(18C)vi | 3.370 |
C(4)···H(13)viii | 3.501 | H(7A)···H(16)i | 2.693 |
C(4)···H(18B)vi | 3.350 | H(7A)···H(17)i | 3.406 |
C(5)···H(3B)iv | 3.167 | H(7A)···H(18A)i | 3.501 |
C(5)···H(7C)iv | 3.513 | H(7B)···H(18A)x | 3.067 |
C(5)···H(18B)vi | 3.234 | H(13)···H(18B)xi | 3.568 |
C(6)···H(4B)i | 3.097 | H(13)···H(18C)iii | 3.200 |
C(7)···H(4A)i | 3.585 | H(14)···H(14)iii | 3.567 |
C(7)···H(4B)i | 3.072 | H(14)···H(14)xi | 3.567 |
C(12)···H(14)iii | 3.330 | H(14)···H(17)vii | 2.798 |
C(12)···H(18B)iii | 3.388 | H(16)···H(18C)iv | 3.159 |
C(12)···H(18C)iii | 3.464 | H(17)···H(18C)iv | 3.430 |
| | | |
O(10)—S(9)—O(11) | 120.1 (2) | H(3A)—C(3)—H(3B) | 109.0 |
O(10)—S(9)—N(1) | 106.5 (2) | C(3)—C(4)—H(4A) | 111.1 |
O(10)—S(9)—C(12) | 107.7 (2) | C(3)—C(4)—H(4B) | 111.1 |
O(11)—S(9)—N(1) | 106.4 (2) | C(5)—C(4)—H(4A) | 111.1 |
O(11)—S(9)—C(12) | 107.5 (2) | C(5)—C(4)—H(4B) | 111.1 |
N(1)—S(9)—C(12) | 108.2 (2) | H(4A)—C(4)—H(4B) | 109.1 |
S(9)—N(1)—C(2) | 117.7 (3) | N(1)—C(5)—H(5A) | 111.0 |
S(9)—N(1)—C(5) | 118.4 (3) | N(1)—C(5)—H(5B) | 111.0 |
C(2)—N(1)—C(5) | 109.8 (3) | C(4)—C(5)—H(5A) | 111.0 |
N(1)—C(2)—C(3) | 102.6 (4) | C(4)—C(5)—H(5B) | 111.0 |
N(1)—C(2)—C(6) | 112.2 (4) | H(5A)—C(5)—H(5B) | 109.0 |
C(3)—C(2)—C(6) | 116.5 (4) | I(8)—C(6)—H(6) | 107.9 |
C(2)—C(3)—C(4) | 104.0 (4) | C(2)—C(6)—H(6) | 107.9 |
C(3)—C(4)—C(5) | 103.2 (4) | C(7)—C(6)—H(6) | 107.9 |
N(1)—C(5)—C(4) | 103.8 (4) | C(6)—C(7)—H(7A) | 109.5 |
I(8)—C(6)—C(2) | 113.2 (3) | C(6)—C(7)—H(7B) | 109.5 |
I(8)—C(6)—C(7) | 109.6 (3) | C(6)—C(7)—H(7C) | 109.5 |
C(2)—C(6)—C(7) | 110.2 (4) | H(7A)—C(7)—H(7B) | 109.5 |
S(9)—C(12)—C(13) | 120.1 (3) | H(7A)—C(7)—H(7C) | 109.5 |
S(9)—C(12)—C(17) | 120.1 (4) | H(7B)—C(7)—H(7C) | 109.5 |
C(13)—C(12)—C(17) | 119.7 (4) | C(12)—C(13)—H(13) | 120.2 |
C(12)—C(13)—C(14) | 119.6 (5) | C(14)—C(13)—H(13) | 120.2 |
C(13)—C(14)—C(15) | 121.8 (5) | C(13)—C(14)—H(14) | 119.1 |
C(14)—C(15)—C(16) | 118.0 (5) | C(15)—C(14)—H(14) | 119.1 |
C(14)—C(15)—C(18) | 121.6 (5) | C(15)—C(16)—H(16) | 119.3 |
C(16)—C(15)—C(18) | 120.4 (5) | C(17)—C(16)—H(16) | 119.3 |
C(15)—C(16)—C(17) | 121.3 (5) | C(12)—C(17)—H(17) | 120.2 |
C(12)—C(17)—C(16) | 119.6 (5) | C(16)—C(17)—H(17) | 120.2 |
N(1)—C(2)—H(2) | 108.4 | C(15)—C(18)—H(18A) | 109.5 |
C(3)—C(2)—H(2) | 108.4 | C(15)—C(18)—H(18B) | 109.5 |
C(6)—C(2)—H(2) | 108.4 | C(15)—C(18)—H(18C) | 109.5 |
C(2)—C(3)—H(3A) | 111.0 | H(18A)—C(18)—H(18B) | 109.5 |
C(2)—C(3)—H(3B) | 111.0 | H(18A)—C(18)—H(18C) | 109.5 |
C(4)—C(3)—H(3A) | 111.0 | H(18B)—C(18)—H(18C) | 109.5 |
C(4)—C(3)—H(3B) | 111.0 | | |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x, y−1/2, −z+3/2; (iii) x−1/2, −y+1/2, −z+1; (iv) x−1, y, z; (v) x−1/2, −y+1/2, −z+2; (vi) −x+1/2, −y+1, z+1/2; (vii) x+1, y, z; (viii) −x+1, y+1/2, −z+3/2; (ix) −x+1/2, −y+1, z−1/2; (x) −x+3/2, −y+1, z+1/2; (xi) x+1/2, −y+1/2, −z+1. |