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To explore the operational role of noncovalent inter­actions in supra­molecular architectures with designed topologies, a series of solid-state structures of 2- and 4-formyl­phenyl 4-substituted benzene­sulfonates was investigated. The com­pounds are 2-formyl­phenyl 4-methyl­benzene­sulfonate, C14H12O4S, 3a, 2-formyl­phenyl 4-chloro­benzene­sulfonate, C13H9ClO4S, 3b, 2-formyl­phenyl 4-bromo­ben­zene­sulfonate, C13H9BrO4S, 3c, 4-formyl­phenyl 4-methyl­benzene­sulfonate, C14H12O4S, 4a, 4-formyl­phenyl 4-chloro­benzene­sulfonate, 4b, C13H9ClO4S, and 4-formyl­phenyl 4-bromo­benzene­sulfonate, C13H9BrO4S, 4c. The title com­pounds were synthesized under basic conditions from salicyl­aldehyde/4-hy­droxy­benzaldehydes and various aryl sul­fonyl chlorides. Remarkably, halogen-bonding inter­actions are found to be important to rationalize the solid-state crystal structures. In particular, the formation of O...X (X = Cl and Br) and type I X...X halogen-bonding inter­actions have been analyzed by means of density functional theory (DFT) calculations and characterized using Bader's theory of `atoms in mol­ecules' and mol­ecular electrostatic potential (MEP) surfaces, confirming the relevance and stabilizing nature of these inter­actions. They have been compared to anti­parallel π-stacking inter­actions that are formed between the aryl­sulfonates.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618008355/rh3006sup1.cif
Contains datablocks global, 3a, 3b, 3c, 4b, 4c

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618008355/rh30063asup2.hkl
Contains datablock 3a

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229618008355/rh3006sup3.pdf
Additional packing plots and spectra

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618008355/rh30063bsup4.hkl
Contains datablock 3b

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618008355/rh30063csup5.hkl
Contains datablock 3c

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618008355/rh30064bsup6.hkl
Contains datablock 4b

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618008355/rh30064csup7.hkl
Contains datablock 4c

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618008355/rh30063asup7.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618008355/rh30063bsup8.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618008355/rh30063csup9.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618008355/rh30064bsup10.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618008355/rh30064csup11.cml
Supplementary material

CCDC references: 1578939; 1578938; 1028148; 1028150; 1028135

Computing details top

Data collection: APEX2 (Bruker, 2011) for (3a), (3b), (4b), (4c); APEX2 (Bruker, 2007) for (3c). Cell refinement: SAINT (Bruker, 2011) for (3a), (3b), (4b), (4c); SAINT (Bruker, 2007) for (3c). Data reduction: SAINT (Bruker, 2011) for (3a), (3b), (4b), (4c); SAINT (Bruker, 2007) for (3c). For all structures, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008). Program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015) for (3a), (3b), (4b), (4c); SHELXL2018 (Sheldrick, 2015) for (3c). For all structures, molecular graphics: Mercury (Macrae et al., 2008). Software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015), enCIFer (Allen et al., 2004), PLATON (Spek, 2009) and WinGX (Farrugia, 2012) for (3a), (3b), (4b), (4c); PLATON (Spek, 2009) and publCIF (Westrip, 2010) for (3c).

2-Formylphenyl 4-methylbenzenesulfonate (3a) top
Crystal data top
C14H12O4SF(000) = 1152
Mr = 276.30Dx = 1.364 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 23.7755 (16) ÅCell parameters from 2730 reflections
b = 8.3718 (5) Åθ = 2.1–27.2°
c = 16.3235 (12) ŵ = 0.25 mm1
β = 124.106 (3)°T = 296 K
V = 2690.3 (3) Å3Prism, white
Z = 80.40 × 0.30 × 0.26 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
2987 independent reflections
Radiation source: fine-focus sealed tube2378 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Detector resolution: 7.80 pixels mm-1θmax = 27.2°, θmin = 2.1°
ω scansh = 3030
Absorption correction: multi-scan
(SADABS; Bruker, 2011)
k = 710
Tmin = 0.593, Tmax = 0.746l = 2020
11160 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.039 w = 1/[σ2(Fo2) + (0.0517P)2 + 1.3907P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.112(Δ/σ)max < 0.001
S = 1.04Δρmax = 0.28 e Å3
2987 reflectionsΔρmin = 0.32 e Å3
174 parametersExtinction correction: SHELXL-2014/7 (Sheldrick 2015b, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0045 (4)
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.16506 (2)0.73107 (5)0.17846 (3)0.05234 (17)
O210.14649 (8)1.07324 (16)0.39949 (13)0.0815 (5)
O30.21404 (5)0.73434 (13)0.29703 (9)0.0478 (3)
O10.12514 (8)0.58997 (15)0.14871 (10)0.0688 (4)
O20.21042 (8)0.75780 (18)0.14989 (12)0.0773 (5)
C10.18769 (7)0.68614 (18)0.35162 (11)0.0413 (4)
C20.16864 (7)0.80182 (18)0.39226 (11)0.0416 (4)
C210.17411 (9)0.9749 (2)0.38059 (13)0.0522 (4)
H210.20011.00890.35760.063*
C30.14532 (9)0.7498 (2)0.44893 (13)0.0540 (4)
H30.13150.82450.47640.065*
C40.14230 (10)0.5905 (2)0.46503 (14)0.0629 (5)
H40.12670.55790.50340.075*
C50.16222 (10)0.4790 (2)0.42479 (14)0.0621 (5)
H50.16040.37090.43640.075*
C60.18484 (9)0.5256 (2)0.36746 (14)0.0532 (4)
H60.19800.45000.33970.064*
C1'0.11354 (8)0.89717 (19)0.15260 (12)0.0447 (4)
C2'0.13768 (9)1.0468 (2)0.15141 (13)0.0519 (4)
H2'0.17901.05730.15820.062*
C3'0.10029 (10)1.1789 (2)0.14023 (14)0.0579 (5)
H3'0.11641.27950.13890.069*
C4'0.03920 (9)1.1659 (2)0.13086 (14)0.0595 (5)
C5'0.01555 (9)1.0150 (3)0.13122 (15)0.0629 (5)
H5'0.02601.00460.12400.075*
C6'0.05215 (9)0.8803 (2)0.14207 (14)0.0553 (4)
H130.03580.77950.14230.066*
C41'0.00108 (13)1.3124 (3)0.1199 (2)0.0946 (8)
H41A0.01281.36940.06130.142*
H41B0.02571.38000.17670.142*
H41C0.04181.28130.11490.142*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0687 (3)0.0473 (3)0.0549 (3)0.00435 (19)0.0431 (2)0.00057 (18)
O210.0999 (11)0.0450 (8)0.1081 (13)0.0103 (7)0.0635 (10)0.0099 (8)
O30.0475 (6)0.0492 (7)0.0550 (7)0.0044 (5)0.0338 (6)0.0037 (5)
O10.0982 (10)0.0441 (7)0.0630 (8)0.0067 (7)0.0444 (8)0.0119 (6)
O20.0988 (11)0.0855 (11)0.0893 (11)0.0196 (8)0.0782 (10)0.0134 (8)
C10.0411 (7)0.0394 (8)0.0437 (8)0.0030 (6)0.0240 (7)0.0022 (6)
C20.0430 (8)0.0391 (8)0.0399 (8)0.0029 (6)0.0215 (7)0.0004 (6)
C210.0597 (10)0.0398 (9)0.0494 (10)0.0023 (7)0.0258 (8)0.0029 (7)
C30.0597 (10)0.0590 (11)0.0495 (10)0.0042 (8)0.0343 (9)0.0017 (8)
C40.0736 (12)0.0641 (12)0.0611 (12)0.0049 (9)0.0439 (10)0.0095 (9)
C50.0740 (12)0.0431 (10)0.0687 (13)0.0047 (9)0.0397 (11)0.0083 (9)
C60.0627 (10)0.0368 (9)0.0590 (10)0.0051 (7)0.0335 (9)0.0005 (7)
C1'0.0493 (8)0.0434 (9)0.0427 (8)0.0014 (7)0.0267 (7)0.0012 (7)
C2'0.0512 (9)0.0517 (10)0.0574 (10)0.0029 (8)0.0333 (8)0.0083 (8)
C3'0.0669 (11)0.0439 (10)0.0625 (11)0.0005 (8)0.0361 (9)0.0089 (8)
C4'0.0594 (10)0.0580 (11)0.0525 (10)0.0110 (9)0.0263 (9)0.0056 (8)
C5'0.0435 (9)0.0739 (13)0.0676 (12)0.0014 (8)0.0289 (9)0.0023 (10)
C6'0.0525 (9)0.0520 (10)0.0607 (11)0.0121 (8)0.0313 (9)0.0050 (8)
C41'0.0931 (17)0.0790 (16)0.106 (2)0.0321 (14)0.0521 (16)0.0097 (14)
Geometric parameters (Å, º) top
S1—O11.4197 (14)C5—H50.9300
S1—O21.4122 (14)C6—H60.9300
S1—O31.6048 (13)C1'—C6'1.378 (2)
S1—C1'1.7414 (16)C1'—C2'1.382 (2)
O21—C211.196 (2)C2'—C3'1.366 (2)
O3—C11.4055 (18)C2'—H2'0.9300
C1—C61.377 (2)C3'—C4'1.377 (3)
C1—C21.386 (2)C3'—H3'0.9300
C2—C31.388 (2)C4'—C5'1.384 (3)
C2—C211.477 (2)C4'—C41'1.504 (3)
C21—H210.9300C5'—C6'1.374 (3)
C3—C41.369 (3)C5'—H5'0.9300
C3—H30.9300C6'—H130.9300
C4—C51.370 (3)C41'—H41A0.9600
C4—H40.9300C41'—H41B0.9600
C5—C61.372 (3)C41'—H41C0.9600
O2—S1—O1120.45 (9)C5—C6—H6120.5
O2—S1—O3102.91 (8)C1—C6—H6120.5
O1—S1—O3108.70 (7)C6'—C1'—C2'120.68 (16)
O2—S1—C1'110.92 (8)C6'—C1'—S1120.02 (13)
O1—S1—C1'109.69 (9)C2'—C1'—S1119.06 (12)
O3—S1—C1'102.41 (7)C3'—C2'—C1'119.45 (15)
C1—O3—S1118.67 (10)C3'—C2'—H2'120.3
C6—C1—C2121.89 (16)C1'—C2'—H2'120.3
C6—C1—O3119.05 (14)C2'—C3'—C4'121.15 (17)
C2—C1—O3118.98 (14)C2'—C3'—H3'119.4
C1—C2—C3117.37 (15)C4'—C3'—H3'119.4
C1—C2—C21123.23 (15)C3'—C4'—C5'118.54 (17)
C3—C2—C21119.37 (15)C3'—C4'—C41'120.7 (2)
O21—C21—C2122.76 (18)C5'—C4'—C41'120.8 (2)
O21—C21—H21118.6C6'—C5'—C4'121.34 (17)
C2—C21—H21118.6C6'—C5'—H5'119.3
C4—C3—C2121.11 (17)C4'—C5'—H5'119.3
C4—C3—H3119.4C5'—C6'—C1'118.82 (16)
C2—C3—H3119.4C5'—C6'—H13120.6
C3—C4—C5120.17 (18)C1'—C6'—H13120.6
C3—C4—H4119.9C4'—C41'—H41A109.5
C5—C4—H4119.9C4'—C41'—H41B109.5
C4—C5—C6120.40 (17)H41A—C41'—H41B109.5
C4—C5—H5119.8C4'—C41'—H41C109.5
C6—C5—H5119.8H41A—C41'—H41C109.5
C5—C6—C1119.04 (17)H41B—C41'—H41C109.5
O2—S1—O3—C1169.91 (11)O3—C1—C6—C5176.85 (15)
O1—S1—O3—C141.12 (13)O2—S1—C1'—C6'157.65 (15)
C1'—S1—O3—C174.90 (12)O1—S1—C1'—C6'22.16 (17)
S1—O3—C1—C682.36 (16)O3—S1—C1'—C6'93.14 (15)
S1—O3—C1—C2100.96 (15)O2—S1—C1'—C2'27.91 (17)
C6—C1—C2—C31.0 (2)O1—S1—C1'—C2'163.40 (13)
O3—C1—C2—C3177.55 (14)O3—S1—C1'—C2'81.30 (15)
C6—C1—C2—C21177.05 (16)C6'—C1'—C2'—C3'0.4 (3)
O3—C1—C2—C210.5 (2)S1—C1'—C2'—C3'174.02 (14)
C1—C2—C21—O21165.78 (17)C1'—C2'—C3'—C4'0.5 (3)
C3—C2—C21—O2116.2 (3)C2'—C3'—C4'—C5'1.1 (3)
C1—C2—C3—C40.9 (3)C2'—C3'—C4'—C41'179.18 (19)
C21—C2—C3—C4177.15 (17)C3'—C4'—C5'—C6'0.9 (3)
C2—C3—C4—C50.2 (3)C41'—C4'—C5'—C6'179.4 (2)
C3—C4—C5—C60.5 (3)C4'—C5'—C6'—C1'0.1 (3)
C4—C5—C6—C10.5 (3)C2'—C1'—C6'—C5'0.6 (3)
C2—C1—C6—C50.3 (3)S1—C1'—C6'—C5'173.78 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O1i0.932.693.579 (2)159
C5—H5···O21ii0.932.543.417 (2)157
C6—H6···O2iii0.932.633.479 (2)151
C2—H2···O3iv0.932.673.504 (2)150
C3—H3···O1v0.932.613.481 (2)157
Symmetry codes: (i) x, y+1, z+1/2; (ii) x, y1, z; (iii) x+1/2, y1/2, z+1/2; (iv) x+1/2, y+1/2, z+1/2; (v) x, y+1, z.
2-Formylphenyl 4-chlorobenzenesulfonate (3b) top
Crystal data top
C13H9ClO4SF(000) = 608
Mr = 296.71Dx = 1.496 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.7066 (8) ÅCell parameters from 2006 reflections
b = 12.9371 (8) Åθ = 1.5–27.2°
c = 7.4310 (4) ŵ = 0.45 mm1
β = 91.565 (3)°T = 296 K
V = 1317.20 (13) Å3Prism, white
Z = 40.40 × 0.32 × 0.28 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
2896 independent reflections
Radiation source: fine-focus sealed tube2006 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
Detector resolution: 7.80 pixels mm-1θmax = 27.2°, θmin = 1.5°
ω scansh = 1717
Absorption correction: multi-scan
(SADABS; Bruker, 2011)
k = 1616
Tmin = 0.685, Tmax = 0.746l = 99
11311 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.116 w = 1/[σ2(Fo2) + (0.0485P)2 + 0.4725P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
2896 reflectionsΔρmax = 0.36 e Å3
172 parametersΔρmin = 0.45 e Å3
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.28424 (4)0.43452 (6)0.60153 (9)0.0689 (2)
O10.33588 (12)0.49402 (18)0.4748 (2)0.0872 (6)
O20.26952 (14)0.32676 (16)0.5784 (3)0.1000 (8)
O30.34086 (11)0.44217 (12)0.7925 (2)0.0612 (4)
C10.38961 (15)0.53411 (18)0.8426 (3)0.0507 (5)
C20.34684 (15)0.60022 (18)0.9646 (3)0.0528 (5)
C210.25199 (17)0.5767 (2)1.0452 (3)0.0652 (7)
H210.22730.51011.03110.078*
O210.20482 (14)0.63759 (17)1.1274 (3)0.0891 (6)
C30.39777 (18)0.6879 (2)1.0160 (3)0.0655 (6)
H30.37010.73451.09520.079*
C40.48940 (19)0.7073 (2)0.9510 (3)0.0720 (7)
H40.52330.76640.98710.086*
C50.53075 (17)0.6391 (2)0.8327 (3)0.0658 (7)
H50.59290.65190.79080.079*
C60.48100 (15)0.5525 (2)0.7761 (3)0.0578 (6)
H60.50830.50700.69470.069*
C1'0.17335 (15)0.49650 (18)0.6435 (3)0.0533 (5)
C2'0.09929 (16)0.43986 (18)0.7179 (3)0.0616 (6)
H2'0.10730.36950.73900.074*
C3'0.01372 (16)0.48809 (18)0.7607 (3)0.0604 (6)
H3'0.03720.45060.80900.072*
C4'0.00447 (16)0.59233 (17)0.7309 (3)0.0551 (5)
Cl4'0.10263 (5)0.65318 (5)0.79106 (11)0.0829 (3)
C5'0.07775 (17)0.64975 (19)0.6559 (4)0.0639 (6)
H5'0.06980.72030.63640.077*
C6'0.16282 (17)0.6009 (2)0.6104 (3)0.0621 (6)
H6'0.21270.63790.55770.074*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0439 (3)0.0876 (5)0.0755 (4)0.0071 (3)0.0080 (3)0.0278 (4)
O10.0500 (10)0.151 (2)0.0610 (10)0.0036 (11)0.0117 (8)0.0141 (11)
O20.0689 (12)0.0872 (15)0.1435 (19)0.0176 (10)0.0034 (12)0.0616 (14)
O30.0480 (9)0.0634 (10)0.0723 (10)0.0054 (7)0.0048 (7)0.0043 (8)
C10.0404 (10)0.0616 (14)0.0499 (11)0.0039 (10)0.0009 (9)0.0024 (10)
C20.0416 (11)0.0661 (14)0.0510 (12)0.0046 (10)0.0039 (9)0.0029 (11)
C210.0517 (13)0.0818 (18)0.0627 (15)0.0018 (12)0.0148 (11)0.0009 (13)
O210.0658 (12)0.0993 (15)0.1041 (15)0.0147 (10)0.0363 (11)0.0075 (12)
C30.0613 (14)0.0751 (17)0.0604 (14)0.0028 (13)0.0059 (11)0.0097 (12)
C40.0607 (15)0.0861 (19)0.0691 (16)0.0177 (13)0.0005 (13)0.0042 (14)
C50.0424 (12)0.099 (2)0.0562 (14)0.0083 (12)0.0047 (10)0.0072 (13)
C60.0405 (11)0.0832 (17)0.0499 (12)0.0077 (11)0.0054 (9)0.0009 (12)
C1'0.0409 (11)0.0567 (14)0.0624 (13)0.0008 (9)0.0057 (10)0.0137 (11)
C2'0.0546 (13)0.0427 (12)0.0884 (17)0.0002 (10)0.0143 (12)0.0077 (11)
C3'0.0487 (12)0.0502 (13)0.0832 (16)0.0034 (10)0.0185 (11)0.0017 (12)
C4'0.0458 (12)0.0521 (13)0.0676 (14)0.0042 (10)0.0073 (10)0.0024 (11)
Cl4'0.0593 (4)0.0659 (4)0.1248 (6)0.0184 (3)0.0245 (4)0.0072 (4)
C5'0.0564 (14)0.0469 (13)0.0887 (17)0.0002 (10)0.0059 (12)0.0089 (12)
C6'0.0464 (12)0.0652 (16)0.0750 (16)0.0103 (11)0.0090 (11)0.0034 (12)
Geometric parameters (Å, º) top
S1—O11.420 (2)C5—C61.372 (4)
S1—O21.418 (2)C5—H50.9300
S1—O31.6015 (18)C6—H60.9300
S1—C1'1.754 (2)C1'—C6'1.379 (3)
O3—C11.409 (3)C1'—C2'1.380 (3)
C1—C61.379 (3)C2'—C3'1.373 (3)
C1—C21.388 (3)C2'—H2'0.9300
C2—C31.381 (3)C3'—C4'1.372 (3)
C2—C211.478 (3)C3'—H3'0.9300
C21—O211.197 (3)C4'—C5'1.379 (3)
C21—H210.9300C4'—Cl4'1.735 (2)
C3—C41.381 (3)C5'—C6'1.377 (3)
C3—H30.9300C5'—H5'0.9300
C4—C51.378 (4)C6'—H6'0.9300
C4—H40.9300
O2—S1—O1121.63 (13)C6—C5—H5119.7
O2—S1—O3103.40 (12)C4—C5—H5119.7
O1—S1—O3108.40 (10)C5—C6—C1118.7 (2)
O2—S1—C1'110.47 (12)C5—C6—H6120.7
O1—S1—C1'108.67 (12)C1—C6—H6120.7
O3—S1—C1'102.45 (9)C6'—C1'—C2'121.1 (2)
C1—O3—S1120.06 (14)C6'—C1'—S1120.18 (17)
C6—C1—C2122.1 (2)C2'—C1'—S1118.62 (18)
C6—C1—O3118.6 (2)C3'—C2'—C1'119.6 (2)
C2—C1—O3119.14 (19)C3'—C2'—H2'120.2
C3—C2—C1117.9 (2)C1'—C2'—H2'120.2
C3—C2—C21120.1 (2)C4'—C3'—C2'119.0 (2)
C1—C2—C21122.0 (2)C4'—C3'—H3'120.5
O21—C21—C2124.4 (3)C2'—C3'—H3'120.5
O21—C21—H21117.8C3'—C4'—C5'122.0 (2)
C2—C21—H21117.8C3'—C4'—Cl4'118.66 (17)
C2—C3—C4120.6 (2)C5'—C4'—Cl4'119.37 (18)
C2—C3—H3119.7C6'—C5'—C4'118.9 (2)
C4—C3—H3119.7C6'—C5'—H5'120.6
C5—C4—C3120.1 (2)C4'—C5'—H5'120.6
C5—C4—H4120.0C5'—C6'—C1'119.4 (2)
C3—C4—H4120.0C5'—C6'—H6'120.3
C6—C5—C4120.6 (2)C1'—C6'—H6'120.3
O2—S1—O3—C1164.22 (16)O3—C1—C6—C5176.4 (2)
O1—S1—O3—C133.87 (18)O2—S1—C1'—C6'158.0 (2)
C1'—S1—O3—C180.89 (17)O1—S1—C1'—C6'22.2 (2)
S1—O3—C1—C680.6 (2)O3—S1—C1'—C6'92.4 (2)
S1—O3—C1—C2103.0 (2)O2—S1—C1'—C2'25.1 (2)
C6—C1—C2—C31.5 (3)O1—S1—C1'—C2'160.89 (18)
O3—C1—C2—C3177.8 (2)O3—S1—C1'—C2'84.5 (2)
C6—C1—C2—C21175.7 (2)C6'—C1'—C2'—C3'0.3 (4)
O3—C1—C2—C210.6 (3)S1—C1'—C2'—C3'176.59 (19)
C3—C2—C21—O2115.4 (4)C1'—C2'—C3'—C4'1.1 (4)
C1—C2—C21—O21167.4 (2)C2'—C3'—C4'—C5'1.4 (4)
C1—C2—C3—C41.6 (4)C2'—C3'—C4'—Cl4'178.25 (19)
C21—C2—C3—C4175.6 (2)C3'—C4'—C5'—C6'0.3 (4)
C2—C3—C4—C50.4 (4)Cl4'—C4'—C5'—C6'179.34 (19)
C3—C4—C5—C61.0 (4)C4'—C5'—C6'—C1'1.1 (4)
C4—C5—C6—C11.1 (4)C2'—C1'—C6'—C5'1.4 (4)
C2—C1—C6—C50.2 (3)S1—C1'—C6'—C5'175.45 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O1i0.932.513.224 (3)134
C2—H2···Cl4ii0.932.813.710 (2)164
C3—H3···O21iii0.932.623.528 (3)165
C5—H5···O21iv0.932.613.266 (3)128
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y1/2, z+3/2; (iii) x, y+1, z+2; (iv) x, y+3/2, z1/2.
2-Formylphenyl 4-bromobenzenesulfonate (3c) top
Crystal data top
C13H9BrO4SZ = 2
Mr = 341.17F(000) = 340
Triclinic, P1Dx = 1.718 Mg m3
a = 7.8282 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.5963 (6) ÅCell parameters from 2262 reflections
c = 10.1139 (6) Åθ = 2.1–27.2°
α = 91.249 (3)°µ = 3.28 mm1
β = 102.818 (2)°T = 296 K
γ = 95.938 (3)°Prism, white
V = 659.38 (7) Å30.40 × 0.32 × 0.24 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
2877 independent reflections
Radiation source: fine-focus sealed tube2262 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
Detector resolution: 7.80 pixels mm-1θmax = 27.2°, θmin = 2.1°
ω scansh = 109
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
k = 1011
Tmin = 0.552, Tmax = 0.746l = 1212
10289 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.031 w = 1/[σ2(Fo2) + (0.0364P)2 + 0.2877P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.080(Δ/σ)max < 0.001
S = 1.02Δρmax = 0.32 e Å3
2877 reflectionsΔρmin = 0.45 e Å3
173 parametersExtinction correction: SHELXL2018 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.098 (4)
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br4'1.14703 (4)0.22424 (4)0.02018 (3)0.07010 (16)
S10.61998 (8)0.46297 (6)0.31643 (6)0.04895 (17)
O210.5722 (4)0.0996 (3)0.1545 (3)0.0986 (8)
O30.5273 (2)0.30005 (18)0.35207 (17)0.0473 (4)
O10.7185 (3)0.5427 (2)0.4386 (2)0.0640 (5)
O20.4785 (3)0.5294 (2)0.2338 (2)0.0677 (5)
C10.6307 (3)0.1930 (3)0.4265 (2)0.0446 (5)
C20.6421 (3)0.0531 (3)0.3600 (3)0.0498 (6)
C210.5530 (4)0.0154 (3)0.2166 (3)0.0656 (7)
H210.4781090.0843340.1720360.079*
C30.7364 (4)0.0560 (3)0.4332 (4)0.0715 (8)
H30.7447160.1514520.3914020.086*
C40.8178 (5)0.0248 (5)0.5668 (5)0.0882 (11)
H40.8822760.0986410.6148710.106*
C50.8050 (4)0.1134 (5)0.6296 (3)0.0834 (10)
H50.8609490.1329260.7204840.100*
C60.7102 (4)0.2258 (4)0.5608 (3)0.0634 (7)
H60.7008260.3200890.6040570.076*
C1'0.7661 (3)0.4047 (2)0.2215 (2)0.0427 (5)
C2'0.7016 (3)0.3527 (3)0.0878 (3)0.0563 (6)
H2'0.5828010.3532350.0472260.068*
C3'0.8152 (4)0.3000 (3)0.0155 (3)0.0615 (7)
H3'0.7738270.2637120.0743870.074*
C4'0.9907 (3)0.3013 (3)0.0771 (3)0.0498 (6)
C5'1.0561 (3)0.3565 (3)0.2092 (3)0.0541 (6)
H5'1.1755960.3589040.2487740.065*
C6'0.9425 (3)0.4080 (3)0.2820 (3)0.0508 (6)
H6'0.9843970.4449030.3716500.061*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br4'0.0547 (2)0.0877 (3)0.0697 (2)0.01169 (15)0.01722 (14)0.00737 (15)
S10.0435 (3)0.0379 (3)0.0630 (4)0.0097 (2)0.0052 (3)0.0061 (3)
O210.117 (2)0.0697 (14)0.1103 (19)0.0003 (13)0.0360 (16)0.0360 (13)
O30.0339 (8)0.0457 (9)0.0610 (10)0.0070 (7)0.0072 (7)0.0032 (7)
O10.0633 (11)0.0495 (10)0.0728 (12)0.0021 (8)0.0063 (9)0.0216 (9)
O20.0577 (11)0.0556 (10)0.0896 (14)0.0268 (9)0.0065 (10)0.0061 (10)
C10.0323 (11)0.0490 (12)0.0537 (13)0.0032 (9)0.0129 (10)0.0056 (10)
C20.0393 (12)0.0420 (12)0.0703 (16)0.0012 (10)0.0185 (11)0.0036 (11)
C210.0667 (18)0.0487 (14)0.0795 (19)0.0021 (13)0.0173 (15)0.0105 (13)
C30.0594 (18)0.0532 (16)0.108 (3)0.0129 (14)0.0259 (18)0.0229 (16)
C40.063 (2)0.096 (3)0.114 (3)0.0243 (19)0.024 (2)0.057 (2)
C50.0599 (19)0.127 (3)0.0607 (18)0.009 (2)0.0060 (15)0.032 (2)
C60.0535 (16)0.0816 (19)0.0546 (15)0.0058 (14)0.0121 (13)0.0008 (14)
C1'0.0366 (12)0.0380 (11)0.0505 (13)0.0036 (9)0.0036 (10)0.0040 (9)
C2'0.0372 (13)0.0709 (16)0.0532 (14)0.0100 (12)0.0070 (11)0.0020 (12)
C3'0.0481 (15)0.0824 (19)0.0481 (14)0.0102 (13)0.0020 (11)0.0088 (13)
C4'0.0417 (13)0.0538 (14)0.0530 (14)0.0042 (11)0.0090 (11)0.0044 (11)
C5'0.0346 (12)0.0680 (16)0.0545 (14)0.0021 (11)0.0008 (10)0.0042 (12)
C6'0.0403 (13)0.0594 (14)0.0461 (13)0.0021 (11)0.0001 (10)0.0015 (11)
Geometric parameters (Å, º) top
Br4'—C4'1.892 (2)C4—C51.359 (5)
Br4'—O21i3.094 (3)C4—H40.9300
S1—O21.4114 (19)C5—C61.384 (5)
S1—O11.4219 (18)C5—H50.9300
S1—O31.5955 (17)C6—H60.9300
S1—C1'1.751 (2)C1'—C6'1.377 (3)
O21—C211.200 (3)C1'—C2'1.382 (3)
O3—C11.408 (3)C2'—C3'1.374 (4)
C1—C61.373 (4)C2'—H2'0.9300
C1—C21.386 (3)C3'—C4'1.375 (4)
C2—C31.380 (4)C3'—H3'0.9300
C2—C211.476 (4)C4'—C5'1.375 (3)
C21—H210.9300C5'—C6'1.373 (4)
C3—C41.367 (5)C5'—H5'0.9300
C3—H30.9300C6'—H6'0.9300
C4'—Br4'—O21i174.78 (9)C4—C5—H5119.4
O2—S1—O1120.49 (11)C6—C5—H5119.4
O2—S1—O3102.58 (11)C1—C6—C5117.6 (3)
O1—S1—O3109.09 (11)C1—C6—H6121.2
O2—S1—C1'111.30 (12)C5—C6—H6121.2
O1—S1—C1'108.95 (11)C6'—C1'—C2'121.1 (2)
O3—S1—C1'102.78 (9)C6'—C1'—S1119.66 (18)
C1—O3—S1119.56 (13)C2'—C1'—S1119.27 (18)
C6—C1—C2122.3 (2)C3'—C2'—C1'119.1 (2)
C6—C1—O3120.4 (2)C3'—C2'—H2'120.4
C2—C1—O3117.2 (2)C1'—C2'—H2'120.4
C3—C2—C1117.9 (3)C2'—C3'—C4'119.5 (2)
C3—C2—C21119.4 (3)C2'—C3'—H3'120.3
C1—C2—C21122.6 (2)C4'—C3'—H3'120.3
O21—C21—C2123.5 (3)C5'—C4'—C3'121.5 (2)
O21—C21—H21118.3C5'—C4'—Br4'118.69 (19)
C2—C21—H21118.3C3'—C4'—Br4'119.78 (19)
C4—C3—C2120.5 (3)C6'—C5'—C4'119.0 (2)
C4—C3—H3119.7C6'—C5'—H5'120.5
C2—C3—H3119.7C4'—C5'—H5'120.5
C5—C4—C3120.3 (3)C5'—C6'—C1'119.7 (2)
C5—C4—H4119.8C5'—C6'—H6'120.1
C3—C4—H4119.8C1'—C6'—H6'120.1
C4—C5—C6121.3 (3)
O2—S1—O3—C1175.36 (17)C4—C5—C6—C10.5 (5)
O1—S1—O3—C155.78 (18)O2—S1—C1'—C6'149.33 (19)
C1'—S1—O3—C159.74 (18)O1—S1—C1'—C6'14.1 (2)
S1—O3—C1—C669.2 (3)O3—S1—C1'—C6'101.5 (2)
S1—O3—C1—C2113.2 (2)O2—S1—C1'—C2'32.2 (2)
C6—C1—C2—C30.4 (4)O1—S1—C1'—C2'167.4 (2)
O3—C1—C2—C3177.2 (2)O3—S1—C1'—C2'77.0 (2)
C6—C1—C2—C21178.4 (2)C6'—C1'—C2'—C3'1.5 (4)
O3—C1—C2—C210.8 (3)S1—C1'—C2'—C3'176.9 (2)
C3—C2—C21—O217.9 (4)C1'—C2'—C3'—C4'0.5 (4)
C1—C2—C21—O21174.1 (3)C2'—C3'—C4'—C5'1.0 (4)
C1—C2—C3—C41.0 (4)C2'—C3'—C4'—Br4'178.4 (2)
C21—C2—C3—C4179.0 (3)C3'—C4'—C5'—C6'1.5 (4)
C2—C3—C4—C50.8 (5)Br4'—C4'—C5'—C6'177.93 (19)
C3—C4—C5—C60.1 (5)C4'—C5'—C6'—C1'0.5 (4)
C2—C1—C6—C50.3 (4)C2'—C1'—C6'—C5'1.0 (4)
O3—C1—C6—C5177.8 (2)S1—C1'—C6'—C5'177.43 (19)
Symmetry code: (i) x+2, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O1ii0.932.683.440 (3)140
C5—H5···O2iii0.932.693.436 (3)138
C6—H6···O1iv0.932.663.406 (3)138
Symmetry codes: (ii) x, y1, z; (iii) x+1, y, z; (iv) x+2, y+1, z+1.
4-Formylphenyl 4-chlorobenzenesulfonate (4b) top
Crystal data top
C13H9ClO4SF(000) = 608
Mr = 296.71Dx = 1.493 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.4670 (5) ÅCell parameters from 1977 reflections
b = 11.9547 (5) Åθ = 2.0–27.0°
c = 10.6575 (4) ŵ = 0.45 mm1
β = 98.045 (1)°T = 296 K
V = 1320.45 (10) Å3Plate, colorless
Z = 40.38 × 0.34 × 0.32 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
2854 independent reflections
Radiation source: fine-focus sealed tube2188 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
Detector resolution: 7.80 pixels mm-1θmax = 27.0°, θmin = 2.0°
ω scansh = 1313
Absorption correction: multi-scan
(SADABS; Bruker, 2011)
k = 1514
Tmin = 0.617, Tmax = 0.746l = 1310
10509 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.107 w = 1/[σ2(Fo2) + (0.0473P)2 + 0.4702P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
2854 reflectionsΔρmax = 0.47 e Å3
172 parametersΔρmin = 0.32 e Å3
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.23967 (5)0.12072 (4)0.43688 (5)0.04835 (17)
O10.15829 (15)0.18133 (13)0.34357 (16)0.0634 (4)
O20.28054 (16)0.16797 (13)0.55797 (15)0.0644 (4)
O30.37398 (13)0.09681 (11)0.38571 (13)0.0506 (4)
C10.37465 (17)0.03426 (16)0.27268 (18)0.0430 (4)
C20.3159 (2)0.07404 (18)0.1574 (2)0.0531 (5)
H20.27260.14220.15160.064*
C30.3231 (2)0.0101 (2)0.0515 (2)0.0558 (6)
H30.28290.03470.02700.067*
C40.3891 (2)0.09025 (19)0.0601 (2)0.0519 (5)
C410.3978 (3)0.1597 (2)0.0542 (3)0.0684 (7)
H410.44640.22500.04340.082*
O410.3479 (2)0.13841 (19)0.15732 (19)0.0921 (6)
C50.4491 (2)0.12623 (18)0.1761 (2)0.0580 (6)
H50.49540.19290.18190.070*
C60.4412 (2)0.06442 (17)0.2839 (2)0.0519 (5)
H60.48040.08930.36260.062*
C1'0.17525 (17)0.01302 (16)0.45191 (18)0.0416 (4)
C2'0.2136 (2)0.07337 (17)0.56100 (19)0.0479 (5)
H2'0.27130.04280.62630.057*
C3'0.1653 (2)0.17974 (18)0.5720 (2)0.0517 (5)
H3'0.18950.22160.64510.062*
C4'0.08076 (19)0.22314 (16)0.4737 (2)0.0480 (5)
Cl4'0.02169 (6)0.35742 (5)0.48752 (7)0.0738 (2)
C5'0.0414 (2)0.16315 (18)0.3655 (2)0.0523 (5)
H5'0.01650.19400.30060.063*
C6'0.08882 (19)0.05639 (18)0.35388 (19)0.0489 (5)
H6'0.06300.01430.28140.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0516 (3)0.0346 (3)0.0577 (3)0.0020 (2)0.0035 (2)0.0046 (2)
O10.0636 (9)0.0503 (9)0.0748 (10)0.0145 (8)0.0047 (8)0.0088 (8)
O20.0781 (11)0.0456 (9)0.0673 (10)0.0033 (8)0.0023 (8)0.0200 (8)
O30.0467 (8)0.0441 (8)0.0599 (9)0.0071 (6)0.0039 (6)0.0044 (7)
C10.0397 (9)0.0387 (10)0.0506 (12)0.0061 (8)0.0064 (8)0.0053 (9)
C20.0509 (12)0.0443 (11)0.0647 (14)0.0064 (9)0.0099 (10)0.0145 (11)
C30.0516 (12)0.0661 (15)0.0487 (13)0.0004 (11)0.0034 (9)0.0152 (11)
C40.0487 (11)0.0523 (12)0.0559 (13)0.0046 (10)0.0111 (9)0.0019 (10)
C410.0713 (16)0.0707 (16)0.0656 (17)0.0011 (13)0.0176 (13)0.0061 (14)
O410.0966 (15)0.1180 (18)0.0602 (12)0.0079 (12)0.0053 (10)0.0137 (12)
C50.0660 (14)0.0449 (12)0.0634 (14)0.0109 (10)0.0099 (11)0.0059 (11)
C60.0557 (12)0.0469 (12)0.0514 (12)0.0068 (10)0.0014 (9)0.0115 (10)
C1'0.0419 (10)0.0367 (10)0.0464 (11)0.0002 (8)0.0067 (8)0.0063 (8)
C2'0.0506 (11)0.0465 (11)0.0442 (11)0.0048 (9)0.0016 (8)0.0029 (9)
C3'0.0539 (12)0.0489 (12)0.0506 (12)0.0006 (10)0.0013 (9)0.0044 (10)
C4'0.0431 (10)0.0370 (10)0.0651 (13)0.0011 (8)0.0116 (9)0.0051 (10)
Cl4'0.0710 (4)0.0433 (3)0.1061 (5)0.0115 (3)0.0091 (3)0.0009 (3)
C5'0.0500 (11)0.0521 (12)0.0524 (12)0.0088 (10)0.0018 (9)0.0121 (10)
C6'0.0500 (11)0.0503 (12)0.0445 (11)0.0028 (9)0.0003 (9)0.0010 (9)
Geometric parameters (Å, º) top
S1—O11.4150 (16)C5—C61.377 (3)
S1—O21.4189 (15)C5—H50.9300
S1—O31.6031 (15)C6—H60.9300
S1—C1'1.7512 (19)C1'—C2'1.379 (3)
O3—C11.419 (2)C1'—C6'1.384 (3)
C1—C61.367 (3)C2'—C3'1.380 (3)
C1—C21.379 (3)C2'—H2'0.9300
C2—C31.374 (3)C3'—C4'1.375 (3)
C2—H20.9300C3'—H3'0.9300
C3—C41.381 (3)C4'—C5'1.372 (3)
C3—H30.9300C4'—Cl4'1.734 (2)
C4—C51.375 (3)Cl4'—Cl4'i3.4542 (12)
C4—C411.488 (3)C5'—C6'1.381 (3)
C41—O411.177 (3)C5'—H5'0.9300
C41—H410.9300C6'—H6'0.9300
O1—S1—O2120.70 (10)C6—C5—H5119.7
O1—S1—O3108.81 (9)C1—C6—C5118.66 (19)
O2—S1—O3102.31 (9)C1—C6—H6120.7
O1—S1—C1'109.28 (10)C5—C6—H6120.7
O2—S1—C1'110.56 (10)C2'—C1'—C6'121.53 (18)
O3—S1—C1'103.63 (8)C2'—C1'—S1118.96 (14)
C1—O3—S1119.44 (11)C6'—C1'—S1119.51 (15)
C6—C1—C2122.3 (2)C1'—C2'—C3'119.14 (18)
C6—C1—O3116.35 (17)C1'—C2'—H2'120.4
C2—C1—O3121.33 (18)C3'—C2'—H2'120.4
C3—C2—C1118.12 (19)C4'—C3'—C2'119.17 (19)
C3—C2—H2120.9C4'—C3'—H3'120.4
C1—C2—H2120.9C2'—C3'—H3'120.4
C2—C3—C4120.8 (2)C5'—C4'—C3'121.93 (19)
C2—C3—H3119.6C5'—C4'—Cl4'119.13 (16)
C4—C3—H3119.6C3'—C4'—Cl4'118.93 (17)
C5—C4—C3119.5 (2)C4'—Cl4'—Cl4'i166.54 (8)
C5—C4—C41119.3 (2)C4'—C5'—C6'119.28 (19)
C3—C4—C41121.2 (2)C4'—C5'—H5'120.4
O41—C41—C4125.0 (3)C6'—C5'—H5'120.4
O41—C41—H41117.5C5'—C6'—C1'118.94 (19)
C4—C41—H41117.5C5'—C6'—H6'120.5
C4—C5—C6120.6 (2)C1'—C6'—H6'120.5
C4—C5—H5119.7
O1—S1—O3—C160.07 (16)O2—S1—C1'—C2'24.81 (19)
O2—S1—O3—C1171.15 (14)O3—S1—C1'—C2'84.18 (17)
C1'—S1—O3—C156.13 (15)O1—S1—C1'—C6'20.97 (19)
S1—O3—C1—C6118.03 (17)O2—S1—C1'—C6'156.12 (16)
S1—O3—C1—C264.8 (2)O3—S1—C1'—C6'94.90 (16)
C6—C1—C2—C31.4 (3)C6'—C1'—C2'—C3'0.5 (3)
O3—C1—C2—C3178.47 (17)S1—C1'—C2'—C3'178.58 (16)
C1—C2—C3—C41.0 (3)C1'—C2'—C3'—C4'0.4 (3)
C2—C3—C4—C50.4 (3)C2'—C3'—C4'—C5'1.0 (3)
C2—C3—C4—C41179.7 (2)C2'—C3'—C4'—Cl4'179.33 (16)
C5—C4—C41—O41178.1 (3)C5'—C4'—Cl4'—Cl4'i113.2 (4)
C3—C4—C41—O412.5 (4)C3'—C4'—Cl4'—Cl4'i67.1 (4)
C3—C4—C5—C61.6 (3)C3'—C4'—C5'—C6'0.7 (3)
C41—C4—C5—C6179.1 (2)Cl4'—C4'—C5'—C6'179.66 (16)
C2—C1—C6—C50.3 (3)C4'—C5'—C6'—C1'0.2 (3)
O3—C1—C6—C5177.51 (18)C2'—C1'—C6'—C5'0.8 (3)
C4—C5—C6—C11.2 (3)S1—C1'—C6'—C5'178.24 (16)
O1—S1—C1'—C2'159.95 (16)
Symmetry code: (i) x, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O2ii0.932.493.266 (3)142
C6—H6···O2iii0.932.703.388 (3)132
C2—H2···O41iv0.932.603.227 (3)125
C3—H3···O41iv0.932.683.267 (3)122
C5—H5···O1v0.932.483.389 (2)166
Symmetry codes: (ii) x, y1/2, z1/2; (iii) x+1, y, z+1; (iv) x, y, z+1; (v) x, y+1/2, z+1/2.
4-Formylphenyl 4-bromobenzenesulfonate (4c) top
Crystal data top
C13H9BrO4SZ = 2
Mr = 341.17F(000) = 340
Triclinic, P1Dx = 1.686 Mg m3
a = 6.8248 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.2849 (4) ÅCell parameters from 1977 reflections
c = 15.1587 (9) Åθ = 3.2–27.9°
α = 79.746 (3)°µ = 3.22 mm1
β = 83.570 (2)°T = 296 K
γ = 65.091 (2)°Needle, white
V = 672.06 (6) Å30.38 × 0.24 × 0.22 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
3167 independent reflections
Radiation source: fine-focus sealed tube1978 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Detector resolution: 7.60 pixels mm-1θmax = 27.9°, θmin = 3.2°
ω scansh = 58
Absorption correction: multi-scan
(SADABS; Bruker, 2011)
k = 99
Tmin = 0.635, Tmax = 0.746l = 1919
11049 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.083 w = 1/[σ2(Fo2) + (0.042P)2 + 0.0141P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
3167 reflectionsΔρmax = 0.26 e Å3
172 parametersΔρmin = 0.29 e Å3
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.33633 (8)0.55505 (8)0.27314 (3)0.05267 (16)
O10.3154 (3)0.4404 (2)0.21135 (10)0.0659 (4)
O20.1717 (2)0.6312 (2)0.33930 (10)0.0690 (4)
O30.3521 (2)0.7588 (2)0.21914 (9)0.0548 (3)
C10.5027 (3)0.7454 (3)0.14598 (13)0.0454 (4)
C20.4574 (3)0.7204 (3)0.06445 (13)0.0497 (5)
H20.33380.70130.05750.060*
C30.5998 (3)0.7242 (3)0.00724 (13)0.0500 (5)
H30.57250.70640.06320.060*
C40.7823 (3)0.7540 (3)0.00292 (13)0.0458 (4)
C410.9258 (3)0.7648 (3)0.07551 (14)0.0563 (5)
H410.89130.74460.12960.068*
O411.0837 (3)0.7976 (3)0.07564 (10)0.0728 (4)
C50.8226 (3)0.7788 (3)0.08671 (13)0.0540 (5)
H50.94500.79950.09400.065*
C60.6847 (3)0.7732 (3)0.15871 (13)0.0548 (5)
H60.71300.78780.21510.066*
C1'0.5890 (3)0.4246 (3)0.32114 (12)0.0459 (5)
C2'0.6329 (3)0.4946 (3)0.39171 (14)0.0591 (5)
H2'0.52770.60790.41470.071*
C3'0.8321 (4)0.3966 (4)0.42789 (16)0.0671 (6)
H3'0.86310.44240.47580.081*
C4'0.9841 (4)0.2321 (4)0.39340 (16)0.0594 (6)
Br4'1.25989 (4)0.09733 (5)0.44290 (2)0.10291 (17)
C5'0.9427 (4)0.1613 (4)0.32313 (17)0.0715 (6)
H5'1.04880.04820.30040.086*
C6'0.7430 (4)0.2586 (3)0.28651 (15)0.0610 (6)
H6'0.71260.21220.23860.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0480 (3)0.0592 (3)0.0510 (3)0.0234 (2)0.0003 (2)0.0064 (3)
O10.0746 (10)0.0763 (10)0.0612 (9)0.0427 (8)0.0122 (7)0.0097 (8)
O20.0512 (8)0.0827 (11)0.0670 (10)0.0250 (8)0.0116 (8)0.0111 (8)
O30.0495 (7)0.0505 (8)0.0568 (8)0.0147 (6)0.0047 (6)0.0080 (7)
C10.0435 (10)0.0391 (10)0.0479 (11)0.0126 (8)0.0035 (9)0.0019 (9)
C20.0454 (11)0.0514 (12)0.0541 (13)0.0215 (9)0.0109 (9)0.0025 (10)
C30.0542 (11)0.0511 (12)0.0472 (11)0.0234 (10)0.0111 (9)0.0033 (9)
C40.0485 (10)0.0385 (10)0.0492 (11)0.0177 (8)0.0045 (9)0.0020 (9)
C410.0623 (13)0.0521 (13)0.0557 (13)0.0258 (11)0.0042 (10)0.0038 (10)
O410.0685 (10)0.0955 (12)0.0683 (10)0.0492 (9)0.0060 (8)0.0120 (9)
C50.0538 (11)0.0626 (13)0.0550 (13)0.0331 (10)0.0110 (10)0.0029 (10)
C60.0609 (13)0.0638 (14)0.0468 (12)0.0314 (11)0.0096 (10)0.0060 (10)
C1'0.0481 (10)0.0487 (12)0.0405 (11)0.0207 (9)0.0034 (8)0.0066 (9)
C2'0.0551 (12)0.0656 (14)0.0576 (13)0.0213 (11)0.0034 (10)0.0239 (11)
C3'0.0668 (15)0.0798 (17)0.0615 (14)0.0333 (13)0.0060 (12)0.0170 (13)
C4'0.0540 (12)0.0606 (14)0.0590 (13)0.0246 (11)0.0068 (10)0.0084 (11)
Br4'0.0686 (2)0.0937 (3)0.1298 (3)0.02494 (17)0.03928 (17)0.02523 (19)
C5'0.0672 (15)0.0551 (14)0.0719 (16)0.0071 (12)0.0045 (12)0.0099 (12)
C6'0.0684 (14)0.0541 (13)0.0535 (13)0.0150 (12)0.0039 (11)0.0151 (11)
Geometric parameters (Å, º) top
S1—O11.4156 (15)C5—C61.365 (3)
S1—O21.4130 (15)C5—H50.9300
S1—O31.6024 (14)C6—H60.9300
S1—C1'1.749 (2)C1'—C6'1.369 (3)
O3—C11.412 (2)C1'—C2'1.374 (3)
C1—C21.367 (3)C2'—C3'1.367 (3)
C1—C61.378 (3)C2'—H2'0.9300
C2—C31.379 (3)C3'—C4'1.356 (3)
C2—H20.9300C3'—H3'0.9300
C3—C41.380 (2)C4'—C5'1.367 (3)
C3—H30.9300C4'—Br4'1.888 (2)
C4—C51.387 (3)Br4'—Br4'i3.4974 (5)
C4—C411.466 (3)C5'—C6'1.372 (3)
C41—O411.198 (2)C5'—H5'0.9300
C41—H410.9300C6'—H6'0.9300
O1—S1—O2120.66 (9)C4—C5—H5119.6
O1—S1—O3109.03 (8)C5—C6—C1118.51 (18)
O2—S1—O3102.66 (8)C5—C6—H6120.7
O1—S1—C1'109.48 (10)C1—C6—H6120.7
O2—S1—C1'110.81 (9)C6'—C1'—C2'120.7 (2)
O3—S1—C1'102.44 (8)C6'—C1'—S1119.99 (16)
C1—O3—S1119.82 (11)C2'—C1'—S1119.30 (15)
C2—C1—C6122.43 (18)C3'—C2'—C1'119.6 (2)
C2—C1—O3119.73 (16)C3'—C2'—H2'120.2
C6—C1—O3117.67 (17)C1'—C2'—H2'120.2
C1—C2—C3118.22 (17)C4'—C3'—C2'119.6 (2)
C1—C2—H2120.9C4'—C3'—H3'120.2
C3—C2—H2120.9C2'—C3'—H3'120.2
C4—C3—C2120.86 (17)C3'—C4'—C5'121.4 (2)
C4—C3—H3119.6C3'—C4'—Br4'119.64 (19)
C2—C3—H3119.6C5'—C4'—Br4'118.91 (18)
C3—C4—C5119.18 (17)C4'—Br4'—Br4'i171.27 (8)
C3—C4—C41119.36 (18)C4'—C5'—C6'119.3 (2)
C5—C4—C41121.43 (17)C4'—C5'—H5'120.3
O41—C41—C4125.4 (2)C6'—C5'—H5'120.3
O41—C41—H41117.3C1'—C6'—C5'119.4 (2)
C4—C41—H41117.3C1'—C6'—H6'120.3
C6—C5—C4120.79 (17)C5'—C6'—H6'120.3
C6—C5—H5119.6
O1—S1—O3—C150.95 (15)O1—S1—C1'—C6'10.64 (19)
O2—S1—O3—C1179.97 (13)O2—S1—C1'—C6'146.14 (16)
C1'—S1—O3—C164.98 (15)O3—S1—C1'—C6'104.96 (17)
S1—O3—C1—C278.78 (19)O1—S1—C1'—C2'171.44 (15)
S1—O3—C1—C6105.78 (18)O2—S1—C1'—C2'35.95 (18)
C6—C1—C2—C30.3 (3)O3—S1—C1'—C2'72.95 (17)
O3—C1—C2—C3174.94 (17)C6'—C1'—C2'—C3'0.3 (3)
C1—C2—C3—C40.5 (3)S1—C1'—C2'—C3'178.23 (17)
C2—C3—C4—C50.5 (3)C1'—C2'—C3'—C4'0.3 (3)
C2—C3—C4—C41177.70 (18)C2'—C3'—C4'—C5'0.2 (4)
C3—C4—C41—O41177.1 (2)C2'—C3'—C4'—Br4'179.70 (16)
C5—C4—C41—O411.1 (3)C3'—C4'—C5'—C6'0.1 (4)
C3—C4—C5—C60.3 (3)Br4'—C4'—C5'—C6'179.79 (17)
C41—C4—C5—C6178.41 (19)C2'—C1'—C6'—C5'0.2 (3)
C4—C5—C6—C11.0 (3)S1—C1'—C6'—C5'178.13 (17)
C2—C1—C6—C51.0 (3)C4'—C5'—C6'—C1'0.1 (3)
O3—C1—C6—C5174.31 (17)
Symmetry code: (i) x+3, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O41ii0.932.603.303 (2)133
C5—H5···O3iii0.932.633.556 (3)173
C3—H3···O1iv0.932.563.418 (2)153
C6—H6···O41v0.932.693.316 (3)125
Symmetry codes: (ii) x1, y, z; (iii) x+1, y1, z; (iv) x+1, y+1, z; (v) x+2, y+1, z.
Selected bond lengths (Å) and angles (°) for 3a3c, 4b and 4c top
3a3b3c4b4c
S1—O11.4122 (14)1.420 (2)1.4219 (18)1.4150 (16)1.4156 (15)
S1—O21.4197 (14)1.418 (2)1.4114 (19)1.4189 (15)1.4130 (15)
S1—O31.6048 (13)1.6015 (18)1.5955 (17)1.6031 (15)1.6024 (14)
S1—C1'1.7414 (16)1.754 (2)1.751 (2)1.7512 (19)1.749 (2)
O3—C11.4055 (18)1.409 (3)1.408 (3)1.419 (2)1.412 (2)
O21—C211.196 (2)1.197 (3)1.200 (3)
O41—C41---1.177 (3)1.198 (2)
C2—C211.477 (2)1.478 (3)1.476 (4)
C4—C41---1.488 (3)1.466 (3)
C4'—C41'1.504 (3)----
C4'—Cl4'-1.735 (2)-1.734 (2)-
C4'—Br4'--1.892 (2)-1.888 (2)
Br4'—O213cx--3.094 (3)--
Cl4'—Cl4'4bx---3.4542 (12)-
Br4'—Br4'4cx----3.4974 (5)
O1—S1—O3108.70 (7)108.40 (10)109.09 (11)108.81 (9)109.03 (8)
O2—S1—O1120.45 (9)121.63 (13)120.49 (11)120.70 (10)120.66 (9)
O2—S1—O3102.91 (8)103.40 (12)102.58 (11)102.31 (9)102.66 (8)
O1—S1—C1'109.69 (9)108.67 (12)108.95 (11)109.28 (10)109.48 (10)
O2—S1—C1'110.92 (8)110.47 (12)111.30 (12)110.56 (10)110.81 (9)
O3—S1—C1'102.41 (7)102.45 (9)102.78 (9)103.63 (8)102.44 (8)
C1—O3—S1118.67 (10)120.06 (14)119.56 (13)119.44 (11)119.82 (11)
O21—C21—C2122.76 (18)124.4 (3)123.5 (3)
O41—C41—C4125.0 (3)125.4 (2)
Symmetry transformations used to generate equivalent atoms: 3cx = -x+2, -y, -z; 4bx = -x, 1-y, 1-z; 4cx = -x+3, -y, -z+1.
Interplanar angles (°) for 3a3c, 4b and 4c top
CompoundC1–C6/C1'–C6'C1–C6/C—CHO
3a41.19 (8)15.5 (4)
3b42.18 (8)14.6 (3)
3c51.87 (9)6.9 (5)
4b53.53 (6)2.5 (4)
4c55.60 (7)2.8 (3)
 

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