N-(4-Chloro­phenyl­sulfon­yl)-4-iodo­benzamide

In the title compound, C₁₃H₉ClINO₃S, the benzene rings are inclined to one another by 81.6 (2)°. In the crystal, mol­ecules are linked by pairs of N—H...O hydrogen bonds, forming inversion dimers with an R₂²(8) ring motif. The dimers are linked by C—H...O hydrogen bonds, forming sheets parallel to the bc plane. Neighbouring sheets are linked via offset π–π inter­actions involving inversion-related iodo­benzene rings [inter­centroid distance = 3.807 (3) Å], forming a three-dimensional supra­molecular structure.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.064
• wR factor = 0.172
• Data-to-parameter ratio = 12.8

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 =    0.5839
PLAT023_ALERT_3_C Resolution (too) Low [sin(theta)/Lambda < 0.6]..      64.20 Degree
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full value Low .      0.978 Note
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.2 Note
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.584         54 Report
PLAT971_ALERT_2_C Check Calcd Residual Density  1.07A From      I1       1.60 eA-3
PLAT972_ALERT_2_C Check Calcd Residual Density  0.71A From      I1      -1.77 eA-3
PLAT972_ALERT_2_C Check Calcd Residual Density  0.76A From      I1      -1.53 eA-3
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Note

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          2 Note
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.14 Report
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          1 Note
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          1 Note
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still          71 % Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   9 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   2 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

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Computing details

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: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

N-(4-Chlorophenylsulfonyl)-4-iodobenzamide

Crystal data

C13H9ClINO3S	F(000) = 1632
Mr = 421.62	Dx = 1.936 Mg m^−3
Monoclinic, C2/c	Melting point: 425 K
Hall symbol: -C 2yc	Cu Kα radiation, λ = 1.54178 Å
a = 18.1163 (18) Å	Cell parameters from 144 reflections
b = 13.3947 (13) Å	θ = 4.2–64.2°
c = 12.3002 (13) Å	µ = 20.51 mm^−1
β = 104.223 (4)°	T = 296 K
V = 2893.3 (5) Å^3	Prism, colourless
Z = 8	0.28 × 0.27 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer	2369 independent reflections
Radiation source: fine-focus sealed tube	2178 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.072
phi and φ scans	θmax = 64.2°, θmin = 4.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −21→20
Tmin = 0.069, Tmax = 0.080	k = −15→15
13818 measured reflections	l = −12→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.172	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.1376P)^2 + 0.079P] where P = (Fo^2 + 2Fc^2)/3
2369 reflections	(Δ/σ)max = 0.001
185 parameters	Δρmax = 1.58 e Å^−3
1 restraint	Δρmin = −1.82 e Å^−3

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σ(F²) is used only for calculating R-factors(gt) 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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.7762 (2)	0.3242 (4)	0.7483 (4)	0.0274 (10)
C2	0.7821 (3)	0.3116 (4)	0.6400 (4)	0.0361 (11)
H2	0.7548	0.2611	0.5958	0.043*
C3	0.8284 (3)	0.3737 (5)	0.5966 (4)	0.0425 (12)
H3	0.8333	0.3650	0.5237	0.051*
C4	0.8676 (3)	0.4492 (4)	0.6636 (5)	0.0370 (12)
C5	0.8628 (3)	0.4624 (4)	0.7727 (5)	0.0391 (12)
H5	0.8902	0.5128	0.8168	0.047*
C6	0.8161 (3)	0.3987 (4)	0.8160 (5)	0.0336 (11)
H6	0.8119	0.4063	0.8894	0.040*
C7	0.8082 (3)	0.0884 (4)	0.8118 (4)	0.0244 (10)
C8	0.8589 (2)	0.0109 (3)	0.8799 (4)	0.0220 (9)
C9	0.9104 (3)	−0.0367 (4)	0.8302 (4)	0.0319 (11)
H9	0.9131	−0.0180	0.7584	0.038*
C10	0.9575 (3)	−0.1108 (4)	0.8851 (4)	0.0334 (11)
H10	0.9926	−0.1413	0.8519	0.040*
C11	0.9518 (2)	−0.1392 (4)	0.9901 (4)	0.0268 (10)
C12	0.9013 (3)	−0.0940 (4)	1.0412 (4)	0.0295 (10)
H12	0.8981	−0.1142	1.1122	0.035*
C13	0.8553 (3)	−0.0179 (3)	0.9861 (4)	0.0264 (10)
H13	0.8217	0.0139	1.0210	0.032*
O1	0.69380 (19)	0.2958 (3)	0.8916 (3)	0.0374 (8)
O2	0.66080 (18)	0.2040 (3)	0.7129 (3)	0.0377 (8)
O3	0.79821 (18)	0.0931 (3)	0.7109 (3)	0.0340 (8)
S1	0.71643 (8)	0.24483 (8)	0.80304 (11)	0.0264 (4)
Cl1	0.92287 (8)	0.52981 (13)	0.60795 (14)	0.0601 (5)
I1	1.02099 (2)	−0.25581 (3)	1.07348 (3)	0.0422 (3)
N1	0.7722 (2)	0.1537 (3)	0.8684 (3)	0.0251 (8)
HN1	0.788 (3)	0.169 (4)	0.934 (3)	0.023 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.029 (2)	0.018 (2)	0.030 (2)	0.0099 (18)	−0.0016 (17)	0.0023 (18)
C2	0.044 (3)	0.025 (3)	0.034 (2)	−0.003 (2)	0.0003 (19)	0.000 (2)
C3	0.052 (3)	0.034 (3)	0.039 (3)	0.000 (2)	0.007 (2)	0.003 (2)
C4	0.031 (2)	0.020 (3)	0.055 (3)	0.005 (2)	0.002 (2)	0.017 (2)
C5	0.037 (2)	0.018 (3)	0.054 (3)	0.004 (2)	−0.003 (2)	0.002 (2)
C6	0.039 (3)	0.016 (3)	0.042 (3)	0.010 (2)	0.003 (2)	0.001 (2)
C7	0.023 (2)	0.017 (3)	0.032 (2)	−0.0035 (18)	0.0049 (17)	−0.0002 (19)
C8	0.024 (2)	0.008 (2)	0.033 (2)	−0.0047 (16)	0.0054 (16)	−0.0032 (17)
C9	0.043 (3)	0.021 (3)	0.035 (2)	0.007 (2)	0.0149 (19)	0.0056 (19)
C10	0.037 (2)	0.023 (3)	0.044 (3)	0.010 (2)	0.017 (2)	0.005 (2)
C11	0.0203 (19)	0.015 (2)	0.041 (2)	0.0018 (17)	0.0004 (17)	−0.0008 (18)
C12	0.039 (2)	0.018 (2)	0.030 (2)	0.0058 (19)	0.0069 (18)	0.0031 (18)
C13	0.029 (2)	0.013 (2)	0.038 (2)	0.0068 (18)	0.0107 (17)	−0.0039 (18)
O1	0.0419 (19)	0.029 (2)	0.0407 (18)	0.0185 (16)	0.0087 (14)	0.0006 (16)
O2	0.0268 (16)	0.030 (2)	0.0481 (19)	0.0005 (15)	−0.0071 (14)	−0.0011 (17)
O3	0.0409 (17)	0.028 (2)	0.0330 (17)	0.0073 (14)	0.0079 (13)	0.0012 (14)
S1	0.0267 (8)	0.0184 (7)	0.0315 (7)	0.0071 (4)	0.0020 (5)	0.0020 (4)
Cl1	0.0554 (9)	0.0455 (9)	0.0771 (10)	−0.0123 (7)	0.0119 (7)	0.0213 (7)
I1	0.0384 (4)	0.0233 (4)	0.0621 (4)	0.01269 (11)	0.0068 (3)	0.01117 (13)
N1	0.0307 (19)	0.016 (2)	0.0258 (19)	0.0058 (16)	0.0024 (14)	−0.0003 (16)

Geometric parameters (Å, º)

C1—C2	1.374 (7)	C8—C13	1.379 (7)
C1—C6	1.385 (8)	C8—C9	1.390 (6)
C1—S1	1.764 (5)	C9—C10	1.374 (7)
C2—C3	1.379 (8)	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.375 (7)
C3—C4	1.385 (8)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.370 (7)
C4—C5	1.377 (8)	C11—I1	2.105 (4)
C4—Cl1	1.725 (5)	C12—C13	1.384 (7)
C5—C6	1.395 (8)	C12—H12	0.9300
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	O1—S1	1.429 (4)
C7—O3	1.211 (6)	O2—S1	1.413 (4)
C7—N1	1.379 (6)	S1—N1	1.661 (4)
C7—C8	1.499 (7)	N1—HN1	0.81 (3)
C2—C1—C6	121.1 (5)	C10—C9—C8	121.2 (4)
C2—C1—S1	119.9 (4)	C10—C9—H9	119.4
C6—C1—S1	119.0 (4)	C8—C9—H9	119.4
C1—C2—C3	120.1 (5)	C9—C10—C11	118.7 (4)
C1—C2—H2	119.9	C9—C10—H10	120.6
C3—C2—H2	119.9	C11—C10—H10	120.6
C2—C3—C4	118.8 (5)	C12—C11—C10	121.5 (4)
C2—C3—H3	120.6	C12—C11—I1	119.3 (3)
C4—C3—H3	120.6	C10—C11—I1	119.3 (3)
C5—C4—C3	121.9 (5)	C11—C12—C13	119.4 (4)
C5—C4—Cl1	119.2 (4)	C11—C12—H12	120.3
C3—C4—Cl1	118.9 (4)	C13—C12—H12	120.3
C4—C5—C6	118.8 (5)	C8—C13—C12	120.4 (4)
C4—C5—H5	120.6	C8—C13—H13	119.8
C6—C5—H5	120.6	C12—C13—H13	119.8
C1—C6—C5	119.2 (5)	O2—S1—O1	120.0 (2)
C1—C6—H6	120.4	O2—S1—N1	109.1 (2)
C5—C6—H6	120.4	O1—S1—N1	103.7 (2)
O3—C7—N1	121.0 (4)	O2—S1—C1	108.6 (2)
O3—C7—C8	121.7 (4)	O1—S1—C1	108.7 (2)
N1—C7—C8	117.2 (4)	N1—S1—C1	105.7 (2)
C13—C8—C9	118.8 (4)	C7—N1—S1	121.9 (3)
C13—C8—C7	124.0 (4)	C7—N1—HN1	125 (4)
C9—C8—C7	117.2 (4)	S1—N1—HN1	109 (4)
C6—C1—C2—C3	0.0 (7)	C9—C10—C11—I1	178.1 (4)
S1—C1—C2—C3	179.7 (4)	C10—C11—C12—C13	−0.2 (7)
C1—C2—C3—C4	−0.9 (8)	I1—C11—C12—C13	−179.4 (3)
C2—C3—C4—C5	1.5 (8)	C9—C8—C13—C12	−1.0 (7)
C2—C3—C4—Cl1	−177.7 (4)	C7—C8—C13—C12	176.5 (4)
C3—C4—C5—C6	−1.1 (7)	C11—C12—C13—C8	1.3 (7)
Cl1—C4—C5—C6	178.1 (4)	C2—C1—S1—O2	−22.7 (4)
C2—C1—C6—C5	0.4 (7)	C6—C1—S1—O2	156.9 (4)
S1—C1—C6—C5	−179.3 (4)	C2—C1—S1—O1	−155.0 (4)
C4—C5—C6—C1	0.2 (7)	C6—C1—S1—O1	24.7 (4)
O3—C7—C8—C13	−159.7 (5)	C2—C1—S1—N1	94.3 (4)
N1—C7—C8—C13	19.3 (6)	C6—C1—S1—N1	−86.1 (4)
O3—C7—C8—C9	17.9 (7)	O3—C7—N1—S1	−2.7 (6)
N1—C7—C8—C9	−163.1 (4)	C8—C7—N1—S1	178.3 (3)
C13—C8—C9—C10	−0.3 (7)	O2—S1—N1—C7	53.2 (4)
C7—C8—C9—C10	−178.0 (5)	O1—S1—N1—C7	−177.7 (4)
C8—C9—C10—C11	1.4 (8)	C1—S1—N1—C7	−63.5 (4)
C9—C10—C11—C12	−1.1 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O1^i	0.81 (4)	2.14 (4)	2.943 (5)	168 (6)
C12—H12···O3^ii	0.93	2.43	3.124 (6)	131

Symmetry codes: (i) −x+3/2, −y+1/2, −z+2; (ii) x, −y, z+1/2.