The title compound, C
14H
12INO
3S, crystallizes with two independent molecules (
A and
B) in the asymmetric unit. The dihedral angle between the two aryl rings is 83.1 (4)° in molecule
A and 79.8 (4)° in molecule
B. In the crystal, the two molecules are linked by a pair of N—H

O hydrogen bonds, forming an
A–
B dimer with an
R22(8) ring motif. The dimer is further strengthened by a pair of C—H

O hydrogen bonds with an
R22(14) motif. Another pair of C—H

O interactions assembles these dimers along the diagonal of the
bc plane, forming ribbons. Adjacent ribbons are connected by C—H

π
aryl interactions between the
A molecules, and thus the overall supramolecular architecture is one-dimensional.
Supporting information
CCDC reference: 1523975
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean
(C-C) = 0.014 Å
- R factor = 0.062
- wR factor = 0.182
- Data-to-parameter ratio = 13.0
checkCIF/PLATON results
No syntax errors found
Alert level C
THETM01_ALERT_3_C The value of sine(theta_max)/wavelength is less than 0.590
Calculated sin(theta_max)/wavelength = 0.5851
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.01379 Ang.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.585 91 Report
PLAT972_ALERT_2_C Check Calcd Residual Density 0.74A From I2 -1.52 eA-3
PLAT975_ALERT_2_C Check Calcd Residual Density 0.85A From O4 0.68 eA-3
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density. 0 Note
Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 2 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check
PLAT072_ALERT_2_G SHELXL First Parameter in WGHT Unusually Large 0.11 Report
PLAT725_ALERT_2_G D-H Calc 0.95000, Rep 0.93000 Dev... 0.02 Ang.
C4 -H4 1.555 1.555 ............ # 66 Check
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still 55 % Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min) 4 Note
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
6 ALERT level G = General information/check it is not something unexpected
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
5 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
1 ALERT type 5 Informative message, check
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: APEX2 (Bruker, 2009); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus and XPREP (Bruker, 2009); program(s) used to solve structure: SHELXT2016 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015b).
4-Iodo-
N-(
o-tolylsulfonyl)benzamide
top
Crystal data top
C14H12INO3S | F(000) = 784 |
Mr = 401.21 | Dx = 1.855 Mg m−3 |
Triclinic, P1 | Melting point: 450 K |
a = 11.0543 (10) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 12.1612 (10) Å | Cell parameters from 133 reflections |
c = 12.3464 (10) Å | θ = 4.0–64.4° |
α = 119.140 (4)° | µ = 18.94 mm−1 |
β = 94.668 (5)° | T = 173 K |
γ = 93.182 (5)° | Prism, colourless |
V = 1436.2 (2) Å3 | 0.25 × 0.12 × 0.07 mm |
Z = 4 | |
Data collection top
Bruker APEXII CCD diffractometer | 3621 reflections with I > 2σ(I) |
Radiation source: sealed X-ray tube | Rint = 0.092 |
ω and φ scans | θmax = 64.4°, θmin = 5.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −12→12 |
Tmin = 0.124, Tmax = 0.266 | k = −14→14 |
17365 measured reflections | l = −14→14 |
4724 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)] = 0.062 | H-atom parameters constrained |
wR(F2) = 0.182 | w = 1/[σ2(Fo2) + (0.113P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
4724 reflections | Δρmax = 1.40 e Å−3 |
363 parameters | Δρmin = −1.39 e Å−3 |
0 restraints | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I1 | 0.99795 (6) | 0.28147 (5) | −0.25297 (5) | 0.0394 (2) | |
S1 | 0.7516 (2) | 0.17454 (18) | 0.35284 (17) | 0.0273 (5) | |
O1 | 0.8316 (6) | 0.1073 (5) | 0.3869 (5) | 0.0318 (13) | |
O2 | 0.7190 (6) | 0.2922 (5) | 0.4501 (5) | 0.0321 (14) | |
O3 | 0.8181 (6) | 0.0118 (5) | 0.1084 (5) | 0.0330 (14) | |
N1 | 0.8113 (7) | 0.2141 (6) | 0.2560 (6) | 0.0269 (15) | |
H1 | 0.827821 | 0.294813 | 0.279541 | 0.032* | |
C1 | 0.6178 (8) | 0.0717 (7) | 0.2660 (7) | 0.0297 (19) | |
C2 | 0.5212 (9) | 0.1108 (8) | 0.2142 (8) | 0.033 (2) | |
C3 | 0.4173 (10) | 0.0220 (9) | 0.1534 (9) | 0.042 (2) | |
H3 | 0.350362 | 0.043818 | 0.117099 | 0.051* | |
C4 | 0.4096 (9) | −0.0963 (8) | 0.1449 (9) | 0.039 (2) | |
H4 | 0.337588 | −0.153414 | 0.103983 | 0.047* | |
C5 | 0.5066 (9) | −0.1317 (8) | 0.1958 (8) | 0.038 (2) | |
H5 | 0.502342 | −0.213616 | 0.187899 | 0.045* | |
C6 | 0.6086 (8) | −0.0465 (7) | 0.2577 (7) | 0.0304 (19) | |
H6 | 0.673931 | −0.068811 | 0.295485 | 0.036* | |
C7 | 0.8359 (8) | 0.1234 (7) | 0.1386 (7) | 0.0256 (18) | |
C8 | 0.8786 (8) | 0.1684 (7) | 0.0545 (7) | 0.0258 (17) | |
C9 | 0.8854 (8) | 0.2944 (8) | 0.0827 (7) | 0.0289 (19) | |
H9 | 0.865884 | 0.357746 | 0.161014 | 0.035* | |
C10 | 0.9214 (9) | 0.3274 (8) | −0.0055 (7) | 0.032 (2) | |
H10 | 0.926372 | 0.413321 | 0.013469 | 0.039* | |
C11 | 0.9497 (9) | 0.2338 (8) | −0.1213 (7) | 0.0316 (19) | |
C12 | 0.9445 (8) | 0.1084 (8) | −0.1473 (7) | 0.0310 (19) | |
H12 | 0.965631 | 0.044622 | −0.224612 | 0.037* | |
C13 | 0.9083 (8) | 0.0768 (8) | −0.0598 (7) | 0.0314 (19) | |
H13 | 0.903828 | −0.009000 | −0.078578 | 0.038* | |
C14 | 0.5249 (10) | 0.2348 (9) | 0.2182 (9) | 0.044 (2) | |
H14A | 0.446169 | 0.241537 | 0.180359 | 0.066* | |
H14B | 0.589802 | 0.241554 | 0.171524 | 0.066* | |
H14C | 0.541018 | 0.303192 | 0.305187 | 0.066* | |
I2 | 0.35056 (6) | 0.47630 (6) | −0.11241 (5) | 0.0407 (2) | |
S2 | 0.1444 (2) | 0.40351 (17) | 0.52510 (17) | 0.0275 (5) | |
O4 | 0.1960 (6) | 0.5154 (5) | 0.6401 (5) | 0.0320 (14) | |
O5 | 0.0172 (6) | 0.3659 (5) | 0.5076 (5) | 0.0355 (14) | |
O6 | 0.1204 (6) | 0.2389 (5) | 0.2576 (5) | 0.0338 (14) | |
N2 | 0.1819 (6) | 0.4363 (6) | 0.4157 (6) | 0.0268 (15) | |
H2 | 0.212606 | 0.513728 | 0.437907 | 0.032* | |
C15 | 0.2244 (9) | 0.2757 (7) | 0.5050 (6) | 0.0288 (19) | |
C16 | 0.3543 (9) | 0.2878 (8) | 0.5247 (7) | 0.034 (2) | |
C17 | 0.4071 (10) | 0.1809 (9) | 0.5084 (8) | 0.041 (2) | |
H17 | 0.493510 | 0.185113 | 0.521427 | 0.049* | |
C18 | 0.3371 (10) | 0.0675 (9) | 0.4733 (8) | 0.041 (2) | |
H18 | 0.376524 | −0.004767 | 0.459878 | 0.049* | |
C19 | 0.2115 (9) | 0.0583 (8) | 0.4578 (7) | 0.035 (2) | |
H19 | 0.164404 | −0.018055 | 0.438802 | 0.042* | |
C20 | 0.1550 (9) | 0.1618 (7) | 0.4703 (7) | 0.032 (2) | |
H20 | 0.068594 | 0.155170 | 0.455117 | 0.038* | |
C21 | 0.1661 (8) | 0.3449 (8) | 0.2899 (7) | 0.0278 (18) | |
C22 | 0.2132 (8) | 0.3842 (8) | 0.2011 (7) | 0.0288 (18) | |
C23 | 0.2159 (9) | 0.2872 (8) | 0.0803 (7) | 0.034 (2) | |
H23 | 0.189032 | 0.202605 | 0.058519 | 0.041* | |
C24 | 0.2564 (9) | 0.3118 (8) | −0.0073 (8) | 0.035 (2) | |
H24 | 0.260178 | 0.244419 | −0.089385 | 0.042* | |
C25 | 0.2927 (9) | 0.4363 (9) | 0.0234 (8) | 0.038 (2) | |
C26 | 0.2897 (9) | 0.5353 (8) | 0.1443 (7) | 0.033 (2) | |
H26 | 0.314058 | 0.620255 | 0.165411 | 0.040* | |
C27 | 0.2505 (9) | 0.5079 (7) | 0.2332 (7) | 0.031 (2) | |
H27 | 0.249286 | 0.574251 | 0.316386 | 0.038* | |
C28 | 0.4340 (10) | 0.4063 (8) | 0.5610 (9) | 0.041 (2) | |
H28A | 0.431842 | 0.466625 | 0.649623 | 0.062* | |
H28B | 0.404602 | 0.443550 | 0.510389 | 0.062* | |
H28C | 0.518041 | 0.386688 | 0.546863 | 0.062* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.0546 (5) | 0.0361 (4) | 0.0307 (3) | −0.0023 (3) | 0.0084 (3) | 0.0191 (2) |
S1 | 0.0345 (12) | 0.0241 (10) | 0.0250 (9) | 0.0008 (8) | 0.0023 (8) | 0.0140 (7) |
O1 | 0.039 (4) | 0.031 (3) | 0.030 (3) | 0.002 (3) | −0.002 (2) | 0.020 (2) |
O2 | 0.046 (4) | 0.026 (3) | 0.024 (3) | −0.004 (3) | 0.008 (2) | 0.013 (2) |
O3 | 0.040 (4) | 0.027 (3) | 0.036 (3) | 0.007 (3) | 0.010 (3) | 0.018 (2) |
N1 | 0.036 (4) | 0.025 (3) | 0.024 (3) | 0.002 (3) | 0.004 (3) | 0.016 (3) |
C1 | 0.039 (6) | 0.025 (4) | 0.023 (4) | 0.002 (4) | 0.000 (3) | 0.011 (3) |
C2 | 0.035 (5) | 0.030 (4) | 0.034 (4) | 0.005 (4) | 0.000 (4) | 0.015 (3) |
C3 | 0.039 (6) | 0.039 (5) | 0.046 (5) | 0.002 (4) | −0.004 (4) | 0.021 (4) |
C4 | 0.030 (5) | 0.033 (5) | 0.044 (5) | 0.000 (4) | −0.002 (4) | 0.012 (4) |
C5 | 0.041 (6) | 0.026 (4) | 0.040 (5) | −0.001 (4) | −0.001 (4) | 0.013 (4) |
C6 | 0.031 (5) | 0.031 (4) | 0.030 (4) | 0.003 (4) | 0.005 (3) | 0.015 (3) |
C7 | 0.024 (5) | 0.019 (4) | 0.033 (4) | −0.003 (3) | 0.000 (3) | 0.014 (3) |
C8 | 0.027 (5) | 0.024 (4) | 0.029 (4) | 0.006 (3) | 0.003 (3) | 0.015 (3) |
C9 | 0.031 (5) | 0.029 (4) | 0.024 (4) | 0.002 (4) | 0.005 (3) | 0.011 (3) |
C10 | 0.050 (6) | 0.024 (4) | 0.024 (4) | −0.004 (4) | 0.004 (4) | 0.013 (3) |
C11 | 0.041 (6) | 0.028 (4) | 0.028 (4) | 0.008 (4) | 0.005 (4) | 0.015 (3) |
C12 | 0.041 (6) | 0.028 (4) | 0.023 (4) | 0.012 (4) | 0.001 (3) | 0.011 (3) |
C13 | 0.037 (5) | 0.024 (4) | 0.033 (4) | 0.002 (4) | 0.003 (4) | 0.013 (3) |
C14 | 0.054 (7) | 0.033 (5) | 0.047 (5) | 0.001 (4) | −0.012 (5) | 0.024 (4) |
I2 | 0.0423 (4) | 0.0562 (4) | 0.0381 (3) | 0.0068 (3) | 0.0069 (3) | 0.0340 (3) |
S2 | 0.0382 (13) | 0.0222 (9) | 0.0259 (9) | 0.0050 (8) | 0.0072 (8) | 0.0142 (7) |
O4 | 0.053 (4) | 0.019 (3) | 0.025 (3) | −0.001 (3) | 0.011 (3) | 0.011 (2) |
O5 | 0.041 (4) | 0.029 (3) | 0.041 (3) | 0.001 (3) | 0.009 (3) | 0.020 (2) |
O6 | 0.048 (4) | 0.021 (3) | 0.031 (3) | 0.001 (3) | 0.001 (3) | 0.013 (2) |
N2 | 0.031 (4) | 0.024 (3) | 0.032 (3) | 0.002 (3) | 0.006 (3) | 0.019 (3) |
C15 | 0.047 (6) | 0.026 (4) | 0.017 (3) | 0.007 (4) | 0.006 (3) | 0.012 (3) |
C16 | 0.046 (6) | 0.038 (5) | 0.030 (4) | 0.011 (4) | 0.014 (4) | 0.024 (4) |
C17 | 0.052 (7) | 0.045 (5) | 0.034 (4) | 0.016 (5) | 0.009 (4) | 0.024 (4) |
C18 | 0.054 (7) | 0.037 (5) | 0.044 (5) | 0.019 (5) | 0.012 (4) | 0.028 (4) |
C19 | 0.053 (7) | 0.023 (4) | 0.033 (4) | 0.003 (4) | 0.002 (4) | 0.017 (3) |
C20 | 0.047 (6) | 0.026 (4) | 0.027 (4) | −0.003 (4) | −0.001 (4) | 0.018 (3) |
C21 | 0.029 (5) | 0.025 (4) | 0.029 (4) | 0.005 (4) | 0.002 (3) | 0.012 (3) |
C22 | 0.032 (5) | 0.029 (4) | 0.029 (4) | 0.000 (4) | −0.001 (3) | 0.018 (3) |
C23 | 0.047 (6) | 0.029 (4) | 0.028 (4) | 0.006 (4) | 0.003 (4) | 0.014 (3) |
C24 | 0.049 (6) | 0.034 (5) | 0.031 (4) | 0.010 (4) | 0.007 (4) | 0.022 (4) |
C25 | 0.041 (6) | 0.052 (6) | 0.033 (4) | 0.007 (4) | −0.002 (4) | 0.029 (4) |
C26 | 0.039 (6) | 0.032 (4) | 0.032 (4) | −0.003 (4) | 0.003 (4) | 0.020 (4) |
C27 | 0.046 (6) | 0.026 (4) | 0.023 (4) | 0.005 (4) | 0.005 (4) | 0.012 (3) |
C28 | 0.044 (6) | 0.036 (5) | 0.051 (5) | 0.002 (4) | 0.002 (4) | 0.028 (4) |
Geometric parameters (Å, º) top
I1—C11 | 2.071 (8) | I2—C25 | 2.095 (9) |
S1—O1 | 1.408 (6) | S2—O5 | 1.420 (7) |
S1—O2 | 1.440 (6) | S2—O4 | 1.447 (6) |
S1—N1 | 1.659 (7) | S2—N2 | 1.659 (6) |
S1—C1 | 1.770 (9) | S2—C15 | 1.753 (8) |
O3—C7 | 1.219 (9) | O6—C21 | 1.213 (10) |
N1—C7 | 1.390 (10) | N2—C21 | 1.389 (10) |
N1—H1 | 0.8800 | N2—H2 | 0.8800 |
C1—C6 | 1.388 (11) | C15—C20 | 1.393 (12) |
C1—C2 | 1.419 (12) | C15—C16 | 1.424 (13) |
C2—C3 | 1.407 (13) | C16—C17 | 1.385 (13) |
C2—C14 | 1.483 (12) | C16—C28 | 1.490 (13) |
C3—C4 | 1.387 (13) | C17—C18 | 1.390 (14) |
C3—H3 | 0.9500 | C17—H17 | 0.9500 |
C4—C5 | 1.392 (13) | C18—C19 | 1.376 (14) |
C4—H4 | 0.9500 | C18—H18 | 0.9500 |
C5—C6 | 1.375 (13) | C19—C20 | 1.383 (12) |
C5—H5 | 0.9500 | C19—H19 | 0.9500 |
C6—H6 | 0.9500 | C20—H20 | 0.9500 |
C7—C8 | 1.485 (11) | C21—C22 | 1.509 (11) |
C8—C13 | 1.387 (11) | C22—C23 | 1.383 (12) |
C8—C9 | 1.392 (12) | C22—C27 | 1.384 (12) |
C9—C10 | 1.409 (11) | C23—C24 | 1.357 (12) |
C9—H9 | 0.9500 | C23—H23 | 0.9500 |
C10—C11 | 1.401 (12) | C24—C25 | 1.395 (13) |
C10—H10 | 0.9500 | C24—H24 | 0.9500 |
C11—C12 | 1.395 (12) | C25—C26 | 1.393 (13) |
C12—C13 | 1.390 (12) | C26—C27 | 1.386 (12) |
C12—H12 | 0.9500 | C26—H26 | 0.9500 |
C13—H13 | 0.9500 | C27—H27 | 0.9500 |
C14—H14A | 0.9800 | C28—H28A | 0.9800 |
C14—H14B | 0.9800 | C28—H28B | 0.9800 |
C14—H14C | 0.9800 | C28—H28C | 0.9800 |
| | | |
O1—S1—O2 | 118.2 (3) | O5—S2—O4 | 118.4 (4) |
O1—S1—N1 | 110.5 (4) | O5—S2—N2 | 110.8 (4) |
O2—S1—N1 | 103.9 (3) | O4—S2—N2 | 103.2 (3) |
O1—S1—C1 | 108.4 (4) | O5—S2—C15 | 109.0 (4) |
O2—S1—C1 | 109.7 (4) | O4—S2—C15 | 109.2 (4) |
N1—S1—C1 | 105.3 (4) | N2—S2—C15 | 105.4 (4) |
C7—N1—S1 | 121.8 (5) | C21—N2—S2 | 121.8 (6) |
C7—N1—H1 | 119.1 | C21—N2—H2 | 119.1 |
S1—N1—H1 | 119.1 | S2—N2—H2 | 119.1 |
C6—C1—C2 | 121.5 (8) | C20—C15—C16 | 121.3 (8) |
C6—C1—S1 | 116.5 (6) | C20—C15—S2 | 117.0 (7) |
C2—C1—S1 | 121.8 (6) | C16—C15—S2 | 121.7 (6) |
C3—C2—C1 | 115.9 (8) | C17—C16—C15 | 116.4 (8) |
C3—C2—C14 | 119.5 (8) | C17—C16—C28 | 119.5 (9) |
C1—C2—C14 | 124.6 (8) | C15—C16—C28 | 124.1 (8) |
C4—C3—C2 | 122.1 (9) | C16—C17—C18 | 121.8 (10) |
C4—C3—H3 | 119.0 | C16—C17—H17 | 119.1 |
C2—C3—H3 | 119.0 | C18—C17—H17 | 119.1 |
C3—C4—C5 | 120.4 (9) | C19—C18—C17 | 121.1 (8) |
C3—C4—H4 | 119.8 | C19—C18—H18 | 119.5 |
C5—C4—H4 | 119.8 | C17—C18—H18 | 119.5 |
C6—C5—C4 | 119.0 (9) | C18—C19—C20 | 119.0 (8) |
C6—C5—H5 | 120.5 | C18—C19—H19 | 120.5 |
C4—C5—H5 | 120.5 | C20—C19—H19 | 120.5 |
C5—C6—C1 | 121.1 (9) | C19—C20—C15 | 120.3 (9) |
C5—C6—H6 | 119.5 | C19—C20—H20 | 119.9 |
C1—C6—H6 | 119.5 | C15—C20—H20 | 119.9 |
O3—C7—N1 | 118.9 (7) | O6—C21—N2 | 119.8 (7) |
O3—C7—C8 | 123.4 (7) | O6—C21—C22 | 123.6 (7) |
N1—C7—C8 | 117.6 (6) | N2—C21—C22 | 116.5 (7) |
C13—C8—C9 | 119.6 (7) | C23—C22—C27 | 120.0 (8) |
C13—C8—C7 | 116.7 (7) | C23—C22—C21 | 115.7 (7) |
C9—C8—C7 | 123.6 (7) | C27—C22—C21 | 124.3 (7) |
C8—C9—C10 | 119.7 (7) | C24—C23—C22 | 120.6 (8) |
C8—C9—H9 | 120.2 | C24—C23—H23 | 119.7 |
C10—C9—H9 | 120.2 | C22—C23—H23 | 119.7 |
C11—C10—C9 | 120.2 (7) | C23—C24—C25 | 119.9 (8) |
C11—C10—H10 | 119.9 | C23—C24—H24 | 120.1 |
C9—C10—H10 | 119.9 | C25—C24—H24 | 120.1 |
C12—C11—C10 | 119.5 (8) | C26—C25—C24 | 120.3 (8) |
C12—C11—I1 | 120.3 (6) | C26—C25—I2 | 119.4 (7) |
C10—C11—I1 | 120.2 (6) | C24—C25—I2 | 120.3 (6) |
C13—C12—C11 | 119.8 (7) | C27—C26—C25 | 118.9 (8) |
C13—C12—H12 | 120.1 | C27—C26—H26 | 120.5 |
C11—C12—H12 | 120.1 | C25—C26—H26 | 120.5 |
C8—C13—C12 | 121.2 (8) | C22—C27—C26 | 120.2 (7) |
C8—C13—H13 | 119.4 | C22—C27—H27 | 119.9 |
C12—C13—H13 | 119.4 | C26—C27—H27 | 119.9 |
C2—C14—H14A | 109.5 | C16—C28—H28A | 109.5 |
C2—C14—H14B | 109.5 | C16—C28—H28B | 109.5 |
H14A—C14—H14B | 109.5 | H28A—C28—H28B | 109.5 |
C2—C14—H14C | 109.5 | C16—C28—H28C | 109.5 |
H14A—C14—H14C | 109.5 | H28A—C28—H28C | 109.5 |
H14B—C14—H14C | 109.5 | H28B—C28—H28C | 109.5 |
| | | |
O1—S1—N1—C7 | 63.1 (7) | O5—S2—N2—C21 | −62.5 (7) |
O2—S1—N1—C7 | −169.1 (6) | O4—S2—N2—C21 | 169.7 (7) |
C1—S1—N1—C7 | −53.8 (7) | C15—S2—N2—C21 | 55.2 (8) |
O1—S1—C1—C6 | 6.3 (7) | O5—S2—C15—C20 | 3.3 (7) |
O2—S1—C1—C6 | −124.1 (6) | O4—S2—C15—C20 | 134.0 (6) |
N1—S1—C1—C6 | 124.6 (6) | N2—S2—C15—C20 | −115.7 (6) |
O1—S1—C1—C2 | −177.6 (6) | O5—S2—C15—C16 | −176.0 (6) |
O2—S1—C1—C2 | 52.0 (8) | O4—S2—C15—C16 | −45.2 (7) |
N1—S1—C1—C2 | −59.3 (8) | N2—S2—C15—C16 | 65.0 (7) |
C6—C1—C2—C3 | −0.6 (12) | C20—C15—C16—C17 | −0.5 (11) |
S1—C1—C2—C3 | −176.5 (7) | S2—C15—C16—C17 | 178.8 (6) |
C6—C1—C2—C14 | −179.3 (8) | C20—C15—C16—C28 | 179.5 (8) |
S1—C1—C2—C14 | 4.8 (12) | S2—C15—C16—C28 | −1.2 (11) |
C1—C2—C3—C4 | 0.1 (14) | C15—C16—C17—C18 | 0.7 (12) |
C14—C2—C3—C4 | 178.9 (9) | C28—C16—C17—C18 | −179.3 (8) |
C2—C3—C4—C5 | −0.7 (15) | C16—C17—C18—C19 | −2.4 (13) |
C3—C4—C5—C6 | 1.8 (14) | C17—C18—C19—C20 | 3.8 (13) |
C4—C5—C6—C1 | −2.4 (13) | C18—C19—C20—C15 | −3.6 (12) |
C2—C1—C6—C5 | 1.8 (12) | C16—C15—C20—C19 | 2.0 (11) |
S1—C1—C6—C5 | 177.9 (7) | S2—C15—C20—C19 | −177.3 (6) |
S1—N1—C7—O3 | −3.3 (11) | S2—N2—C21—O6 | 2.3 (12) |
S1—N1—C7—C8 | 174.6 (6) | S2—N2—C21—C22 | −175.2 (6) |
O3—C7—C8—C13 | −5.3 (13) | O6—C21—C22—C23 | −8.0 (13) |
N1—C7—C8—C13 | 177.0 (8) | N2—C21—C22—C23 | 169.4 (8) |
O3—C7—C8—C9 | 172.1 (8) | O6—C21—C22—C27 | 171.0 (9) |
N1—C7—C8—C9 | −5.6 (12) | N2—C21—C22—C27 | −11.6 (13) |
C13—C8—C9—C10 | 0.5 (13) | C27—C22—C23—C24 | 0.9 (14) |
C7—C8—C9—C10 | −176.8 (8) | C21—C22—C23—C24 | 180.0 (9) |
C8—C9—C10—C11 | 0.2 (14) | C22—C23—C24—C25 | −1.8 (15) |
C9—C10—C11—C12 | −1.3 (14) | C23—C24—C25—C26 | 1.3 (15) |
C9—C10—C11—I1 | 178.3 (7) | C23—C24—C25—I2 | −178.2 (7) |
C10—C11—C12—C13 | 1.6 (14) | C24—C25—C26—C27 | 0.2 (14) |
I1—C11—C12—C13 | −178.0 (7) | I2—C25—C26—C27 | 179.6 (7) |
C9—C8—C13—C12 | −0.2 (13) | C23—C22—C27—C26 | 0.6 (14) |
C7—C8—C13—C12 | 177.4 (8) | C21—C22—C27—C26 | −178.4 (8) |
C11—C12—C13—C8 | −0.9 (14) | C25—C26—C27—C22 | −1.1 (14) |
Hydrogen-bond geometry (Å, º) topCg is the centroid of the iodobenzene ring (C8–C13) of molecule A |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O4i | 0.88 | 2.06 | 2.900 (10) | 158 |
N2—H2···O2i | 0.88 | 2.12 | 2.970 (10) | 161 |
C9—H9···O4i | 0.95 | 2.36 | 3.301 (10) | 170 |
C13—H13···O6ii | 0.95 | 2.56 | 3.378 (11) | 144 |
C23—H23···O3ii | 0.95 | 2.40 | 3.201 (11) | 142 |
C27—H27···O2i | 0.95 | 2.51 | 3.428 (9) | 163 |
C4—H4···Cgiii | 0.93 | 2.81 | 3.656 (11) | 151 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z; (iii) −x+1, −y+2, −z+2. |