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The title compound, C14H12INO3S, 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 AB 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...πar­yl inter­actions between the A mol­ecules, and thus the overall supra­molecular architecture is one-dimensional.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314616020307/su4116sup1.cif
Contains datablocks I, Global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314616020307/su4116Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314616020307/su4116Isup3.cml
Supplementary material

CCDC reference: 1523975

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](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

Computing details top

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
C14H12INO3SF(000) = 784
Mr = 401.21Dx = 1.855 Mg m3
Triclinic, P1Melting point: 450 K
a = 11.0543 (10) ÅCu Kα radiation, λ = 1.54178 Å
b = 12.1612 (10) ÅCell parameters from 133 reflections
c = 12.3464 (10) Åθ = 4.0–64.4°
α = 119.140 (4)°µ = 18.94 mm1
β = 94.668 (5)°T = 173 K
γ = 93.182 (5)°Prism, colourless
V = 1436.2 (2) Å30.25 × 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 tubeRint = 0.092
ω and φ scansθmax = 64.4°, θmin = 5.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1212
Tmin = 0.124, Tmax = 0.266k = 1414
17365 measured reflectionsl = 1414
4724 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.062H-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 reflectionsΔρmax = 1.40 e Å3
363 parametersΔρmin = 1.39 e Å3
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
xyzUiso*/Ueq
I10.99795 (6)0.28147 (5)0.25297 (5)0.0394 (2)
S10.7516 (2)0.17454 (18)0.35284 (17)0.0273 (5)
O10.8316 (6)0.1073 (5)0.3869 (5)0.0318 (13)
O20.7190 (6)0.2922 (5)0.4501 (5)0.0321 (14)
O30.8181 (6)0.0118 (5)0.1084 (5)0.0330 (14)
N10.8113 (7)0.2141 (6)0.2560 (6)0.0269 (15)
H10.8278210.2948130.2795410.032*
C10.6178 (8)0.0717 (7)0.2660 (7)0.0297 (19)
C20.5212 (9)0.1108 (8)0.2142 (8)0.033 (2)
C30.4173 (10)0.0220 (9)0.1534 (9)0.042 (2)
H30.3503620.0438180.1170990.051*
C40.4096 (9)0.0963 (8)0.1449 (9)0.039 (2)
H40.3375880.1534140.1039830.047*
C50.5066 (9)0.1317 (8)0.1958 (8)0.038 (2)
H50.5023420.2136160.1878990.045*
C60.6086 (8)0.0465 (7)0.2577 (7)0.0304 (19)
H60.6739310.0688110.2954850.036*
C70.8359 (8)0.1234 (7)0.1386 (7)0.0256 (18)
C80.8786 (8)0.1684 (7)0.0545 (7)0.0258 (17)
C90.8854 (8)0.2944 (8)0.0827 (7)0.0289 (19)
H90.8658840.3577460.1610140.035*
C100.9214 (9)0.3274 (8)0.0055 (7)0.032 (2)
H100.9263720.4133210.0134690.039*
C110.9497 (9)0.2338 (8)0.1213 (7)0.0316 (19)
C120.9445 (8)0.1084 (8)0.1473 (7)0.0310 (19)
H120.9656310.0446220.2246120.037*
C130.9083 (8)0.0768 (8)0.0598 (7)0.0314 (19)
H130.9038280.0090000.0785780.038*
C140.5249 (10)0.2348 (9)0.2182 (9)0.044 (2)
H14A0.4461690.2415370.1803590.066*
H14B0.5898020.2415540.1715240.066*
H14C0.5410180.3031920.3051870.066*
I20.35056 (6)0.47630 (6)0.11241 (5)0.0407 (2)
S20.1444 (2)0.40351 (17)0.52510 (17)0.0275 (5)
O40.1960 (6)0.5154 (5)0.6401 (5)0.0320 (14)
O50.0172 (6)0.3659 (5)0.5076 (5)0.0355 (14)
O60.1204 (6)0.2389 (5)0.2576 (5)0.0338 (14)
N20.1819 (6)0.4363 (6)0.4157 (6)0.0268 (15)
H20.2126060.5137280.4379070.032*
C150.2244 (9)0.2757 (7)0.5050 (6)0.0288 (19)
C160.3543 (9)0.2878 (8)0.5247 (7)0.034 (2)
C170.4071 (10)0.1809 (9)0.5084 (8)0.041 (2)
H170.4935100.1851130.5214270.049*
C180.3371 (10)0.0675 (9)0.4733 (8)0.041 (2)
H180.3765240.0047670.4598780.049*
C190.2115 (9)0.0583 (8)0.4578 (7)0.035 (2)
H190.1644040.0180550.4388020.042*
C200.1550 (9)0.1618 (7)0.4703 (7)0.032 (2)
H200.0685940.1551700.4551170.038*
C210.1661 (8)0.3449 (8)0.2899 (7)0.0278 (18)
C220.2132 (8)0.3842 (8)0.2011 (7)0.0288 (18)
C230.2159 (9)0.2872 (8)0.0803 (7)0.034 (2)
H230.1890320.2026050.0585190.041*
C240.2564 (9)0.3118 (8)0.0073 (8)0.035 (2)
H240.2601780.2444190.0893850.042*
C250.2927 (9)0.4363 (9)0.0234 (8)0.038 (2)
C260.2897 (9)0.5353 (8)0.1443 (7)0.033 (2)
H260.3140580.6202550.1654110.040*
C270.2505 (9)0.5079 (7)0.2332 (7)0.031 (2)
H270.2492860.5742510.3163860.038*
C280.4340 (10)0.4063 (8)0.5610 (9)0.041 (2)
H28A0.4318420.4666250.6496230.062*
H28B0.4046020.4435500.5103890.062*
H28C0.5180410.3866880.5468630.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0546 (5)0.0361 (4)0.0307 (3)0.0023 (3)0.0084 (3)0.0191 (2)
S10.0345 (12)0.0241 (10)0.0250 (9)0.0008 (8)0.0023 (8)0.0140 (7)
O10.039 (4)0.031 (3)0.030 (3)0.002 (3)0.002 (2)0.020 (2)
O20.046 (4)0.026 (3)0.024 (3)0.004 (3)0.008 (2)0.013 (2)
O30.040 (4)0.027 (3)0.036 (3)0.007 (3)0.010 (3)0.018 (2)
N10.036 (4)0.025 (3)0.024 (3)0.002 (3)0.004 (3)0.016 (3)
C10.039 (6)0.025 (4)0.023 (4)0.002 (4)0.000 (3)0.011 (3)
C20.035 (5)0.030 (4)0.034 (4)0.005 (4)0.000 (4)0.015 (3)
C30.039 (6)0.039 (5)0.046 (5)0.002 (4)0.004 (4)0.021 (4)
C40.030 (5)0.033 (5)0.044 (5)0.000 (4)0.002 (4)0.012 (4)
C50.041 (6)0.026 (4)0.040 (5)0.001 (4)0.001 (4)0.013 (4)
C60.031 (5)0.031 (4)0.030 (4)0.003 (4)0.005 (3)0.015 (3)
C70.024 (5)0.019 (4)0.033 (4)0.003 (3)0.000 (3)0.014 (3)
C80.027 (5)0.024 (4)0.029 (4)0.006 (3)0.003 (3)0.015 (3)
C90.031 (5)0.029 (4)0.024 (4)0.002 (4)0.005 (3)0.011 (3)
C100.050 (6)0.024 (4)0.024 (4)0.004 (4)0.004 (4)0.013 (3)
C110.041 (6)0.028 (4)0.028 (4)0.008 (4)0.005 (4)0.015 (3)
C120.041 (6)0.028 (4)0.023 (4)0.012 (4)0.001 (3)0.011 (3)
C130.037 (5)0.024 (4)0.033 (4)0.002 (4)0.003 (4)0.013 (3)
C140.054 (7)0.033 (5)0.047 (5)0.001 (4)0.012 (5)0.024 (4)
I20.0423 (4)0.0562 (4)0.0381 (3)0.0068 (3)0.0069 (3)0.0340 (3)
S20.0382 (13)0.0222 (9)0.0259 (9)0.0050 (8)0.0072 (8)0.0142 (7)
O40.053 (4)0.019 (3)0.025 (3)0.001 (3)0.011 (3)0.011 (2)
O50.041 (4)0.029 (3)0.041 (3)0.001 (3)0.009 (3)0.020 (2)
O60.048 (4)0.021 (3)0.031 (3)0.001 (3)0.001 (3)0.013 (2)
N20.031 (4)0.024 (3)0.032 (3)0.002 (3)0.006 (3)0.019 (3)
C150.047 (6)0.026 (4)0.017 (3)0.007 (4)0.006 (3)0.012 (3)
C160.046 (6)0.038 (5)0.030 (4)0.011 (4)0.014 (4)0.024 (4)
C170.052 (7)0.045 (5)0.034 (4)0.016 (5)0.009 (4)0.024 (4)
C180.054 (7)0.037 (5)0.044 (5)0.019 (5)0.012 (4)0.028 (4)
C190.053 (7)0.023 (4)0.033 (4)0.003 (4)0.002 (4)0.017 (3)
C200.047 (6)0.026 (4)0.027 (4)0.003 (4)0.001 (4)0.018 (3)
C210.029 (5)0.025 (4)0.029 (4)0.005 (4)0.002 (3)0.012 (3)
C220.032 (5)0.029 (4)0.029 (4)0.000 (4)0.001 (3)0.018 (3)
C230.047 (6)0.029 (4)0.028 (4)0.006 (4)0.003 (4)0.014 (3)
C240.049 (6)0.034 (5)0.031 (4)0.010 (4)0.007 (4)0.022 (4)
C250.041 (6)0.052 (6)0.033 (4)0.007 (4)0.002 (4)0.029 (4)
C260.039 (6)0.032 (4)0.032 (4)0.003 (4)0.003 (4)0.020 (4)
C270.046 (6)0.026 (4)0.023 (4)0.005 (4)0.005 (4)0.012 (3)
C280.044 (6)0.036 (5)0.051 (5)0.002 (4)0.002 (4)0.028 (4)
Geometric parameters (Å, º) top
I1—C112.071 (8)I2—C252.095 (9)
S1—O11.408 (6)S2—O51.420 (7)
S1—O21.440 (6)S2—O41.447 (6)
S1—N11.659 (7)S2—N21.659 (6)
S1—C11.770 (9)S2—C151.753 (8)
O3—C71.219 (9)O6—C211.213 (10)
N1—C71.390 (10)N2—C211.389 (10)
N1—H10.8800N2—H20.8800
C1—C61.388 (11)C15—C201.393 (12)
C1—C21.419 (12)C15—C161.424 (13)
C2—C31.407 (13)C16—C171.385 (13)
C2—C141.483 (12)C16—C281.490 (13)
C3—C41.387 (13)C17—C181.390 (14)
C3—H30.9500C17—H170.9500
C4—C51.392 (13)C18—C191.376 (14)
C4—H40.9500C18—H180.9500
C5—C61.375 (13)C19—C201.383 (12)
C5—H50.9500C19—H190.9500
C6—H60.9500C20—H200.9500
C7—C81.485 (11)C21—C221.509 (11)
C8—C131.387 (11)C22—C231.383 (12)
C8—C91.392 (12)C22—C271.384 (12)
C9—C101.409 (11)C23—C241.357 (12)
C9—H90.9500C23—H230.9500
C10—C111.401 (12)C24—C251.395 (13)
C10—H100.9500C24—H240.9500
C11—C121.395 (12)C25—C261.393 (13)
C12—C131.390 (12)C26—C271.386 (12)
C12—H120.9500C26—H260.9500
C13—H130.9500C27—H270.9500
C14—H14A0.9800C28—H28A0.9800
C14—H14B0.9800C28—H28B0.9800
C14—H14C0.9800C28—H28C0.9800
O1—S1—O2118.2 (3)O5—S2—O4118.4 (4)
O1—S1—N1110.5 (4)O5—S2—N2110.8 (4)
O2—S1—N1103.9 (3)O4—S2—N2103.2 (3)
O1—S1—C1108.4 (4)O5—S2—C15109.0 (4)
O2—S1—C1109.7 (4)O4—S2—C15109.2 (4)
N1—S1—C1105.3 (4)N2—S2—C15105.4 (4)
C7—N1—S1121.8 (5)C21—N2—S2121.8 (6)
C7—N1—H1119.1C21—N2—H2119.1
S1—N1—H1119.1S2—N2—H2119.1
C6—C1—C2121.5 (8)C20—C15—C16121.3 (8)
C6—C1—S1116.5 (6)C20—C15—S2117.0 (7)
C2—C1—S1121.8 (6)C16—C15—S2121.7 (6)
C3—C2—C1115.9 (8)C17—C16—C15116.4 (8)
C3—C2—C14119.5 (8)C17—C16—C28119.5 (9)
C1—C2—C14124.6 (8)C15—C16—C28124.1 (8)
C4—C3—C2122.1 (9)C16—C17—C18121.8 (10)
C4—C3—H3119.0C16—C17—H17119.1
C2—C3—H3119.0C18—C17—H17119.1
C3—C4—C5120.4 (9)C19—C18—C17121.1 (8)
C3—C4—H4119.8C19—C18—H18119.5
C5—C4—H4119.8C17—C18—H18119.5
C6—C5—C4119.0 (9)C18—C19—C20119.0 (8)
C6—C5—H5120.5C18—C19—H19120.5
C4—C5—H5120.5C20—C19—H19120.5
C5—C6—C1121.1 (9)C19—C20—C15120.3 (9)
C5—C6—H6119.5C19—C20—H20119.9
C1—C6—H6119.5C15—C20—H20119.9
O3—C7—N1118.9 (7)O6—C21—N2119.8 (7)
O3—C7—C8123.4 (7)O6—C21—C22123.6 (7)
N1—C7—C8117.6 (6)N2—C21—C22116.5 (7)
C13—C8—C9119.6 (7)C23—C22—C27120.0 (8)
C13—C8—C7116.7 (7)C23—C22—C21115.7 (7)
C9—C8—C7123.6 (7)C27—C22—C21124.3 (7)
C8—C9—C10119.7 (7)C24—C23—C22120.6 (8)
C8—C9—H9120.2C24—C23—H23119.7
C10—C9—H9120.2C22—C23—H23119.7
C11—C10—C9120.2 (7)C23—C24—C25119.9 (8)
C11—C10—H10119.9C23—C24—H24120.1
C9—C10—H10119.9C25—C24—H24120.1
C12—C11—C10119.5 (8)C26—C25—C24120.3 (8)
C12—C11—I1120.3 (6)C26—C25—I2119.4 (7)
C10—C11—I1120.2 (6)C24—C25—I2120.3 (6)
C13—C12—C11119.8 (7)C27—C26—C25118.9 (8)
C13—C12—H12120.1C27—C26—H26120.5
C11—C12—H12120.1C25—C26—H26120.5
C8—C13—C12121.2 (8)C22—C27—C26120.2 (7)
C8—C13—H13119.4C22—C27—H27119.9
C12—C13—H13119.4C26—C27—H27119.9
C2—C14—H14A109.5C16—C28—H28A109.5
C2—C14—H14B109.5C16—C28—H28B109.5
H14A—C14—H14B109.5H28A—C28—H28B109.5
C2—C14—H14C109.5C16—C28—H28C109.5
H14A—C14—H14C109.5H28A—C28—H28C109.5
H14B—C14—H14C109.5H28B—C28—H28C109.5
O1—S1—N1—C763.1 (7)O5—S2—N2—C2162.5 (7)
O2—S1—N1—C7169.1 (6)O4—S2—N2—C21169.7 (7)
C1—S1—N1—C753.8 (7)C15—S2—N2—C2155.2 (8)
O1—S1—C1—C66.3 (7)O5—S2—C15—C203.3 (7)
O2—S1—C1—C6124.1 (6)O4—S2—C15—C20134.0 (6)
N1—S1—C1—C6124.6 (6)N2—S2—C15—C20115.7 (6)
O1—S1—C1—C2177.6 (6)O5—S2—C15—C16176.0 (6)
O2—S1—C1—C252.0 (8)O4—S2—C15—C1645.2 (7)
N1—S1—C1—C259.3 (8)N2—S2—C15—C1665.0 (7)
C6—C1—C2—C30.6 (12)C20—C15—C16—C170.5 (11)
S1—C1—C2—C3176.5 (7)S2—C15—C16—C17178.8 (6)
C6—C1—C2—C14179.3 (8)C20—C15—C16—C28179.5 (8)
S1—C1—C2—C144.8 (12)S2—C15—C16—C281.2 (11)
C1—C2—C3—C40.1 (14)C15—C16—C17—C180.7 (12)
C14—C2—C3—C4178.9 (9)C28—C16—C17—C18179.3 (8)
C2—C3—C4—C50.7 (15)C16—C17—C18—C192.4 (13)
C3—C4—C5—C61.8 (14)C17—C18—C19—C203.8 (13)
C4—C5—C6—C12.4 (13)C18—C19—C20—C153.6 (12)
C2—C1—C6—C51.8 (12)C16—C15—C20—C192.0 (11)
S1—C1—C6—C5177.9 (7)S2—C15—C20—C19177.3 (6)
S1—N1—C7—O33.3 (11)S2—N2—C21—O62.3 (12)
S1—N1—C7—C8174.6 (6)S2—N2—C21—C22175.2 (6)
O3—C7—C8—C135.3 (13)O6—C21—C22—C238.0 (13)
N1—C7—C8—C13177.0 (8)N2—C21—C22—C23169.4 (8)
O3—C7—C8—C9172.1 (8)O6—C21—C22—C27171.0 (9)
N1—C7—C8—C95.6 (12)N2—C21—C22—C2711.6 (13)
C13—C8—C9—C100.5 (13)C27—C22—C23—C240.9 (14)
C7—C8—C9—C10176.8 (8)C21—C22—C23—C24180.0 (9)
C8—C9—C10—C110.2 (14)C22—C23—C24—C251.8 (15)
C9—C10—C11—C121.3 (14)C23—C24—C25—C261.3 (15)
C9—C10—C11—I1178.3 (7)C23—C24—C25—I2178.2 (7)
C10—C11—C12—C131.6 (14)C24—C25—C26—C270.2 (14)
I1—C11—C12—C13178.0 (7)I2—C25—C26—C27179.6 (7)
C9—C8—C13—C120.2 (13)C23—C22—C27—C260.6 (14)
C7—C8—C13—C12177.4 (8)C21—C22—C27—C26178.4 (8)
C11—C12—C13—C80.9 (14)C25—C26—C27—C221.1 (14)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the iodobenzene ring (C8–C13) of molecule A
D—H···AD—HH···AD···AD—H···A
N1—H1···O4i0.882.062.900 (10)158
N2—H2···O2i0.882.122.970 (10)161
C9—H9···O4i0.952.363.301 (10)170
C13—H13···O6ii0.952.563.378 (11)144
C23—H23···O3ii0.952.403.201 (11)142
C27—H27···O2i0.952.513.428 (9)163
C4—H4···Cgiii0.932.813.656 (11)151
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z; (iii) x+1, y+2, z+2.
 

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