Literature DB >> 21583425

Poly[hemi-μ-aqua-[μ-2-(2-bromobenzenesulfonamido)benzoato]sodium(I)].

Islam Ullah Khan, Muhammad Nadeem Arshad, Mehmet Akkurt, Ghulam Mustafa, Muhammad Shafiq.   

Abstract

The asymmetric unit of the title compound, [Na(C(13)H(9)BrNO(4)S)(H(2)O)(0.5)](n), contains two Na(+) cations, two substituted benzoate anions and one water molecule of crystallization. The Na(+) cations are coordinated in an octa-hedral geometry by two carboxyl-ate O atoms, two sulfonyl O atoms and two water O atoms. The latter two ligands occupy trans positions. The polymeric network structure of the title complex is characterized by a layered assembly parallel to (001) and is further consolidated by N-H⋯O, O-H⋯O and C-H⋯O hydrogen-bonding inter-actions.

Entities:  

Year:  2009        PMID： 21583425      PMCID： PMC2977212          DOI： 10.1107/S1600536809028505

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the physical properties of metal complexes of anthranilic acid derivatives, see: Chacko & Parameswaran (1984 ▶). For 2-(4-bromo­benzene­sulfonamido) benzoic acid, see: Arshad et al. (2009 ▶).

Experimental

Crystal data

[Na(C13H9BrNO4S)(H2O)0.5] M = 387.18 Triclinic, a = 9.1683 (6) Å b = 9.2722 (5) Å c = 18.4183 (12) Å α = 97.717 (2)° β = 101.837 (2)° γ = 101.467 (2)° V = 1476.64 (16) Å3 Z = 4 Mo Kα radiation μ = 2.97 mm−1 T = 296 K 0.21 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.574, T max = 0.755 28784 measured reflections 6503 independent reflections 3926 reflections with I > 2σ(I) R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.049 wR(F 2) = 0.125 S = 1.01 6503 reflections 394 parameters 3 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.79 e Å−3 Δρmin = −0.78 e Å−3 Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809028505/fj2240sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028505/fj2240Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Na(C13H9BrNO4S)(H2O)0.5]Z = 4
Mr = 387.18F(000) = 772
Triclinic, P1Dx = 1.742 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.1683 (6) ÅCell parameters from 6020 reflections
b = 9.2722 (5) Åθ = 2.3–27.3°
c = 18.4183 (12) ŵ = 2.97 mm−1
α = 97.717 (2)°T = 296 K
β = 101.837 (2)°Rod like, white
γ = 101.467 (2)°0.21 × 0.12 × 0.10 mm
V = 1476.64 (16) Å3
Bruker Kappa APEXII CCD area-detector diffractometer6503 independent reflections
Radiation source: sealed tube3926 reflections with I > 2σ(I)
graphiteRint = 0.045
φ and ω scansθmax = 27.3°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2007)h = −11→11
Tmin = 0.574, Tmax = 0.755k = −11→11
28784 measured reflectionsl = −23→23
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H atoms treated by a mixture of independent and constrained refinement
S = 1.01w = 1/[σ2(Fo2) + (0.0517P)2 + 1.0386P] where P = (Fo2 + 2Fc2)/3
6503 reflections(Δ/σ)max < 0.001
394 parametersΔρmax = 0.79 e Å−3
3 restraintsΔρmin = −0.78 e Å−3
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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.
xyzUiso*/Ueq
Br10.18494 (11)0.21756 (9)0.03270 (3)0.1272 (4)
Br20.67855 (10)0.41062 (7)0.04707 (4)0.1172 (3)
S10.30302 (9)0.42033 (9)0.38850 (5)0.0285 (3)
S20.65226 (10)−0.10753 (12)0.24430 (5)0.0439 (3)
Na10.52561 (13)0.19278 (13)0.50701 (7)0.0316 (4)
Na2−0.05909 (14)−0.09081 (14)0.41846 (7)0.0344 (4)
O10.3932 (2)0.3272 (3)0.42249 (13)0.0385 (8)
O20.3634 (3)0.5784 (2)0.40534 (13)0.0405 (8)
O3−0.0218 (2)0.1828 (2)0.46798 (12)0.0319 (7)
O4−0.2643 (3)0.1894 (3)0.46144 (16)0.0469 (9)
O50.6421 (3)−0.2446 (3)0.19591 (15)0.0580 (11)
O60.7791 (3)−0.0561 (3)0.30905 (14)0.0546 (10)
O70.4069 (2)−0.0348 (2)0.39614 (12)0.0332 (7)
O80.1636 (2)−0.0201 (3)0.38076 (13)0.0401 (8)
O90.2820 (3)0.1057 (2)0.53176 (13)0.0327 (7)
N10.1423 (3)0.3765 (3)0.41057 (16)0.0347 (9)
N20.5022 (3)−0.1155 (4)0.27713 (17)0.0491 (10)
C10.2647 (4)0.3679 (3)0.28966 (19)0.0328 (11)
C20.3375 (5)0.4607 (5)0.2488 (2)0.0538 (14)
C30.3153 (6)0.4152 (6)0.1727 (3)0.0702 (19)
C40.2172 (6)0.2803 (5)0.1381 (2)0.0633 (18)
C50.1437 (7)0.1906 (5)0.1779 (3)0.081 (2)
C60.1672 (5)0.2339 (4)0.2550 (2)0.0611 (14)
C70.0134 (3)0.4363 (3)0.39122 (18)0.0286 (10)
C80.0127 (4)0.5507 (4)0.3489 (2)0.0389 (11)
C9−0.1154 (4)0.6063 (4)0.3323 (2)0.0446 (14)
C10−0.2422 (4)0.5563 (4)0.3587 (2)0.0438 (14)
C11−0.2430 (4)0.4413 (4)0.3987 (2)0.0367 (11)
C12−0.1186 (3)0.3762 (3)0.41430 (17)0.0267 (10)
C13−0.1356 (4)0.2409 (3)0.45114 (18)0.0291 (10)
C140.6572 (4)0.0334 (4)0.1895 (2)0.0457 (14)
C150.6580 (6)0.1769 (5)0.2209 (2)0.0680 (18)
C160.6661 (6)0.2892 (5)0.1785 (3)0.0773 (19)
C170.6725 (6)0.2564 (5)0.1053 (3)0.0692 (19)
C180.6702 (6)0.1148 (5)0.0723 (3)0.0756 (18)
C190.6622 (5)0.0020 (5)0.1150 (2)0.0612 (18)
C200.3492 (4)−0.1496 (4)0.23536 (19)0.0381 (11)
C210.2373 (4)−0.1206 (4)0.27352 (18)0.0322 (11)
C220.0858 (4)−0.1555 (4)0.2323 (2)0.0406 (12)
C230.0440 (5)−0.2195 (5)0.1569 (2)0.0541 (14)
C240.1548 (5)−0.2464 (5)0.1205 (2)0.0607 (16)
C250.3066 (5)−0.2097 (5)0.1589 (2)0.0558 (16)
C260.2723 (4)−0.0542 (3)0.35624 (18)0.0302 (11)
H10.133700.308000.437600.0420*
HW10.247 (8)0.094 (7)0.4844 (9)0.1760*
H20.51700−0.097000.325400.0590*
HW20.293 (8)0.022 (4)0.544 (3)0.1760*
H2A0.401100.553300.272700.0640*
H30.366200.475200.144700.0850*
H50.077300.099800.153400.0980*
H60.117400.172700.282800.0730*
H80.099000.588800.332100.0470*
H9−0.116500.679700.302500.0530*
H10−0.326100.599300.349800.0520*
H11−0.329600.406000.415900.0440*
H150.653000.198500.271000.0820*
H160.667200.386300.199900.0930*
H180.674000.094100.022000.0900*
H190.66010−0.095000.093100.0740*
H220.01040−0.135000.256300.0490*
H23−0.05850−0.244100.130900.0650*
H240.12740−0.289700.069700.0730*
H250.38120−0.225400.133400.0670*
U11U22U33U12U13U23
Br10.2170 (9)0.1298 (6)0.0341 (3)0.0553 (6)0.0201 (4)0.0057 (3)
Br20.2026 (8)0.0792 (4)0.0861 (5)0.0425 (4)0.0478 (5)0.0360 (3)
S10.0220 (4)0.0325 (4)0.0320 (5)0.0049 (3)0.0073 (3)0.0101 (3)
S20.0370 (5)0.0752 (7)0.0311 (5)0.0319 (5)0.0131 (4)0.0143 (5)
Na10.0244 (7)0.0336 (6)0.0399 (8)0.0075 (5)0.0109 (6)0.0117 (6)
Na20.0261 (7)0.0479 (8)0.0318 (7)0.0108 (6)0.0085 (6)0.0104 (6)
O10.0250 (12)0.0518 (14)0.0440 (14)0.0131 (11)0.0083 (11)0.0210 (12)
O20.0386 (14)0.0347 (12)0.0416 (15)−0.0033 (11)0.0075 (11)0.0051 (11)
O30.0236 (12)0.0375 (12)0.0389 (13)0.0098 (10)0.0089 (10)0.0160 (10)
O40.0295 (14)0.0436 (14)0.082 (2)0.0143 (11)0.0289 (13)0.0282 (13)
O50.0666 (19)0.0757 (19)0.0493 (17)0.0421 (16)0.0262 (15)0.0145 (14)
O60.0321 (14)0.103 (2)0.0388 (15)0.0332 (14)0.0083 (12)0.0223 (15)
O70.0240 (12)0.0496 (13)0.0278 (12)0.0119 (10)0.0056 (10)0.0092 (10)
O80.0240 (12)0.0632 (15)0.0354 (14)0.0117 (11)0.0105 (11)0.0099 (12)
O90.0264 (12)0.0397 (12)0.0367 (13)0.0106 (10)0.0118 (11)0.0126 (10)
N10.0278 (15)0.0407 (15)0.0464 (18)0.0139 (12)0.0161 (13)0.0251 (14)
N20.0321 (17)0.091 (2)0.0281 (16)0.0255 (17)0.0076 (14)0.0066 (16)
C10.0330 (19)0.0325 (17)0.0337 (19)0.0104 (15)0.0060 (16)0.0079 (15)
C20.057 (3)0.056 (2)0.043 (2)−0.002 (2)0.013 (2)0.012 (2)
C30.091 (4)0.082 (3)0.048 (3)0.017 (3)0.033 (3)0.027 (3)
C40.100 (4)0.063 (3)0.031 (2)0.032 (3)0.011 (2)0.011 (2)
C50.127 (5)0.048 (3)0.049 (3)−0.001 (3)0.001 (3)0.003 (2)
C60.091 (3)0.043 (2)0.039 (2)−0.002 (2)0.011 (2)0.0057 (19)
C70.0239 (17)0.0301 (16)0.0336 (18)0.0083 (14)0.0079 (14)0.0076 (14)
C80.036 (2)0.0375 (18)0.050 (2)0.0107 (16)0.0171 (18)0.0173 (17)
C90.049 (2)0.0348 (19)0.059 (3)0.0169 (17)0.016 (2)0.0243 (18)
C100.033 (2)0.041 (2)0.063 (3)0.0189 (16)0.0107 (19)0.0151 (18)
C110.0260 (18)0.0369 (18)0.051 (2)0.0092 (15)0.0145 (16)0.0101 (16)
C120.0241 (17)0.0291 (16)0.0280 (17)0.0074 (13)0.0076 (14)0.0048 (13)
C130.0289 (19)0.0299 (16)0.0317 (18)0.0081 (14)0.0126 (15)0.0066 (14)
C140.041 (2)0.067 (3)0.033 (2)0.0240 (19)0.0076 (17)0.0076 (18)
C150.096 (4)0.077 (3)0.033 (2)0.035 (3)0.014 (2)−0.003 (2)
C160.112 (4)0.060 (3)0.057 (3)0.027 (3)0.016 (3)−0.003 (2)
C170.097 (4)0.066 (3)0.051 (3)0.024 (3)0.024 (3)0.016 (2)
C180.124 (4)0.074 (3)0.037 (2)0.035 (3)0.025 (3)0.012 (2)
C190.095 (4)0.065 (3)0.034 (2)0.031 (2)0.025 (2)0.012 (2)
C200.0310 (19)0.057 (2)0.0279 (19)0.0157 (17)0.0054 (16)0.0082 (16)
C210.0297 (19)0.0387 (18)0.0288 (18)0.0075 (15)0.0068 (15)0.0098 (15)
C220.031 (2)0.057 (2)0.031 (2)0.0047 (17)0.0067 (16)0.0079 (17)
C230.035 (2)0.079 (3)0.041 (2)0.009 (2)−0.0014 (19)0.008 (2)
C240.053 (3)0.084 (3)0.031 (2)0.011 (2)−0.005 (2)−0.007 (2)
C250.050 (3)0.084 (3)0.036 (2)0.025 (2)0.012 (2)0.003 (2)
C260.0288 (19)0.0336 (17)0.0322 (19)0.0081 (14)0.0100 (16)0.0143 (14)
Br1—C41.894 (4)C7—C81.398 (5)
Br2—C171.898 (5)C7—C121.401 (4)
S1—O11.428 (3)C8—C91.369 (5)
S1—O21.427 (2)C9—C101.372 (5)
S1—N11.598 (3)C10—C111.375 (5)
S1—C11.762 (3)C11—C121.391 (5)
S2—O51.426 (3)C12—C131.501 (4)
S2—O61.435 (3)C14—C191.376 (5)
S2—N21.605 (3)C14—C151.376 (6)
S2—C141.754 (4)C15—C161.382 (6)
Na1—O12.408 (3)C16—C171.358 (8)
Na1—O72.613 (2)C17—C181.365 (7)
Na1—O92.377 (3)C18—C191.390 (6)
Na1—O4i2.257 (3)C20—C211.405 (5)
Na1—O7ii2.514 (2)C20—C251.387 (5)
Na1—O2iii2.386 (2)C21—C221.390 (5)
Na2—O32.508 (2)C21—C261.507 (5)
Na2—O82.292 (2)C22—C231.378 (5)
Na2—O6iv2.346 (3)C23—C241.371 (6)
Na2—O3v2.397 (2)C24—C251.377 (6)
Na2—O9v2.393 (3)C2—H2A0.9300
O3—C131.269 (4)C3—H30.9300
O4—C131.244 (5)C5—H50.9300
O7—C261.265 (4)C6—H60.9300
O8—C261.253 (4)C8—H80.9300
O9—HW20.86 (4)C9—H90.9300
O9—HW10.849 (19)C10—H100.9300
N1—C71.404 (4)C11—H110.9300
N2—C201.405 (5)C15—H150.9300
N1—H10.8600C16—H160.9300
N2—H20.8600C18—H180.9300
C1—C61.364 (5)C19—H190.9300
C1—C21.380 (5)C22—H220.9300
C2—C31.369 (6)C23—H230.9300
C3—C41.372 (7)C24—H240.9300
C4—C51.352 (7)C25—H250.9300
C5—C61.382 (6)
Br1···C23vi3.691 (4)C22···C63.488 (5)
Br1···H19vii3.1600C22···Na23.939 (4)
Br1···H23vi3.0600C22···C53.462 (6)
S1···H82.8000C22···C9viii3.541 (5)
S2···H252.7900C23···Br1vi3.691 (4)
Na1···C11i3.849 (4)C25···C143.430 (6)
Na2···C8viii3.633 (4)C25···O53.103 (5)
Na2···C9viii2.926 (4)C25···C3viii3.537 (7)
Na2···C10viii3.290 (4)C1···H82.9000
Na2···C223.939 (4)C9···H16iv3.0200
Na1···H2ii3.4000C9···H22x3.0800
Na1···HW2ii3.01 (6)C10···H16iv3.0000
Na1···H11i3.0400C11···H15iv2.8800
Na2···HW12.90 (7)C12···H15iv3.0400
Na2···HW23.44 (7)C13···HW2v2.60 (4)
Na2···H9viii2.6900C13···H12.5000
Na2···H10viii3.2900C14···H253.0100
Na2···H223.1700C19···H253.1000
Na2···H1v3.6300C20···H2Aviii3.0300
O1···O93.229 (3)C22···H63.0000
O2···C83.117 (5)C22···H9viii2.8000
O3···N12.588 (3)C22···H52.9400
O3···O9v3.212 (3)C23···H52.9300
O3···O93.054 (3)C25···H3viii3.0600
O4···O7iv3.195 (3)C26···HW12.65 (4)
O4···O9v2.730 (3)C26···H22.5200
O5···C253.103 (5)C26···H63.0700
O6···O9ii3.171 (3)H1···O31.8800
O6···C13i3.378 (4)H1···C132.5000
O7···O93.184 (3)H1···HW12.5800
O7···O4i3.195 (3)H1···Na2v3.6300
O7···O9ii3.124 (3)HW1···Na22.90 (7)
O7···N22.595 (4)HW1···O81.97 (3)
O8···O92.768 (3)HW1···C262.65 (4)
O9···C13v3.311 (3)HW1···H12.5800
O9···O82.768 (3)H2···O71.9000
O9···O33.054 (3)H2···C262.5200
O9···O3v3.212 (3)H2···Na1ii3.4000
O9···Na1ii3.634 (3)H2···O9ii2.9100
O9···O4v2.730 (3)H2···HW2ii2.5800
O9···O6ii3.171 (3)HW2···Na23.44 (7)
O9···O13.229 (3)HW2···Na1ii3.01 (6)
O9···O73.184 (3)HW2···O4v1.91 (4)
O9···Na23.390 (3)HW2···C13v2.60 (5)
O9···C263.347 (4)HW2···H2ii2.5800
O9···O7ii3.124 (3)H2A···O22.5200
O1···H11i2.5300H2A···C20x3.0300
O1···HW12.81 (6)H2A···H10i2.5300
O2···H2A2.5200H3···C25x3.0600
O2···H82.5500H5···C222.9400
O3···HW12.72 (7)H5···C232.9300
O3···HW2v2.76 (6)H6···O82.7400
O3···H11.8800H6···N12.7500
O4···HW2v1.91 (4)H6···C223.0000
O4···H112.4100H6···C263.0700
O5···H252.4800H8···S12.8000
O5···H9ix2.9100H8···O22.5500
O5···H192.5100H8···C12.9000
O6···H9ix2.8000H9···Na2x2.6900
O6···H22i2.6900H9···O5xi2.9100
O6···HW2ii2.91 (6)H9···O6xi2.8000
O7···H21.9000H9···C22x2.8000
O7···HW12.72 (6)H9···H22x2.2400
O7···HW2ii2.72 (7)H10···Na2x3.2900
O8···H62.7400H10···H2Aiv2.5300
O8···H222.4100H11···Na1iv3.0400
O8···HW11.97 (3)H11···O1iv2.5300
O9···H2ii2.9100H11···O42.4100
N1···O32.588 (3)H15···C11i2.8800
N2···O72.595 (4)H15···C12i3.0400
N1···H62.7500H16···C9i3.0200
C1···C83.391 (5)H16···C10i3.0000
C3···C25x3.537 (7)H19···O52.5100
C5···C223.462 (6)H19···Br1vii3.1600
C6···C213.519 (5)H22···Na23.1700
C6···C223.488 (5)H22···O6iv2.6900
C8···C13.391 (5)H22···O82.4100
C8···Na2x3.633 (4)H22···C9viii3.0800
C8···O23.117 (5)H22···H9viii2.2400
C9···Na2x2.926 (4)H23···Br1vi3.0600
C9···C22x3.541 (5)H25···S22.7900
C10···Na2x3.290 (4)H25···O52.4800
C11···Na1iv3.849 (4)H25···C143.0100
C14···C253.430 (6)H25···C193.1000
C21···C63.519 (5)
O1—S1—O2118.46 (16)C1—C6—C5119.0 (4)
O1—S1—N1105.18 (14)N1—C7—C12118.2 (3)
O1—S1—C1108.71 (15)N1—C7—C8122.1 (3)
O2—S1—N1111.26 (16)C8—C7—C12119.8 (3)
O2—S1—C1106.36 (14)C7—C8—C9119.8 (3)
N1—S1—C1106.28 (16)C8—C9—C10121.5 (3)
O5—S2—O6118.57 (17)C9—C10—C11118.7 (4)
O5—S2—N2110.77 (18)C10—C11—C12122.1 (3)
O5—S2—C14107.61 (17)C7—C12—C11117.9 (3)
O6—S2—N2105.12 (16)C7—C12—C13123.5 (3)
O6—S2—C14107.31 (17)C11—C12—C13118.4 (3)
N2—S2—C14106.88 (18)O3—C13—O4123.6 (3)
O1—Na1—O783.84 (8)O3—C13—C12119.3 (3)
O1—Na1—O984.90 (8)O4—C13—C12117.0 (3)
O1—Na1—O4i100.77 (10)C15—C14—C19119.4 (4)
O1—Na1—O7ii164.17 (9)S2—C14—C15120.3 (3)
O1—Na1—O2iii89.44 (9)S2—C14—C19120.4 (3)
O7—Na1—O979.17 (8)C14—C15—C16120.5 (4)
O4i—Na1—O781.64 (9)C15—C16—C17119.3 (4)
O7—Na1—O7ii94.55 (7)C16—C17—C18121.6 (5)
O2iii—Na1—O7171.85 (9)Br2—C17—C16118.9 (4)
O4i—Na1—O9159.29 (10)Br2—C17—C18119.5 (4)
O7ii—Na1—O979.34 (8)C17—C18—C19119.0 (5)
O2iii—Na1—O9104.87 (10)C14—C19—C18120.2 (4)
O4i—Na1—O7ii94.55 (9)N2—C20—C21117.8 (3)
O2iii—Na1—O4i95.16 (11)N2—C20—C25122.4 (4)
O2iii—Na1—O7ii93.16 (8)C21—C20—C25119.8 (4)
O3—Na2—O885.24 (9)C20—C21—C22117.8 (3)
O3—Na2—O6iv87.43 (9)C20—C21—C26123.8 (3)
O3—Na2—O3v101.63 (8)C22—C21—C26118.4 (3)
O3—Na2—O9v81.86 (8)C21—C22—C23122.0 (4)
O6iv—Na2—O895.51 (10)C22—C23—C24119.4 (4)
O3v—Na2—O8103.49 (9)C23—C24—C25120.3 (3)
O8—Na2—O9v167.10 (10)C20—C25—C24120.6 (4)
O3v—Na2—O6iv159.49 (10)O8—C26—C21116.6 (3)
O6iv—Na2—O9v84.00 (10)O7—C26—O8124.2 (3)
O3v—Na2—O9v79.20 (8)O7—C26—C21119.3 (3)
S1—O1—Na1165.86 (15)C1—C2—H2A120.00
S1—O2—Na1iii151.44 (15)C3—C2—H2A120.00
Na2—O3—C13117.57 (18)C2—C3—H3120.00
Na2—O3—Na2v78.37 (7)C4—C3—H3120.00
Na2v—O3—C13127.0 (2)C4—C5—H5120.00
Na1iv—O4—C13156.3 (2)C6—C5—H5120.00
S2—O6—Na2i152.55 (18)C1—C6—H6121.00
Na1—O7—C26121.54 (18)C5—C6—H6121.00
Na1—O7—Na1ii85.45 (8)C7—C8—H8120.00
Na1ii—O7—C26122.43 (18)C9—C8—H8120.00
Na2—O8—C26149.8 (2)C8—C9—H9119.00
Na1—O9—Na2v162.49 (11)C10—C9—H9119.00
Na1—O9—HW2100 (5)C9—C10—H10121.00
HW1—O9—HW2110 (6)C11—C10—H10121.00
Na1—O9—HW186 (5)C10—C11—H11119.00
Na2v—O9—HW291 (5)C12—C11—H11119.00
Na2v—O9—HW1104 (5)C14—C15—H15120.00
S1—N1—C7127.9 (2)C16—C15—H15120.00
S2—N2—C20126.9 (3)C15—C16—H16120.00
S1—N1—H1116.00C17—C16—H16120.00
C7—N1—H1116.00C17—C18—H18120.00
S2—N2—H2117.00C19—C18—H18120.00
C20—N2—H2117.00C14—C19—H19120.00
S1—C1—C6119.4 (3)C18—C19—H19120.00
C2—C1—C6121.0 (3)C21—C22—H22119.00
S1—C1—C2119.5 (3)C23—C22—H22119.00
C1—C2—C3119.4 (4)C22—C23—H23120.00
C2—C3—C4119.4 (5)C24—C23—H23120.00
Br1—C4—C3119.5 (4)C23—C24—H24120.00
Br1—C4—C5119.2 (4)C25—C24—H24120.00
C3—C4—C5121.3 (4)C20—C25—H25120.00
C4—C5—C6120.0 (4)C24—C25—H25120.00
O1—S1—O2—Na1iii−52.3 (4)Na2v—O3—C13—C12138.1 (2)
N1—S1—O2—Na1iii69.8 (4)Na2v—O3—C13—O4−44.1 (4)
C1—S1—O2—Na1iii−174.9 (3)Na2—O3—C13—C12−125.7 (2)
O1—S1—N1—C7179.8 (3)Na2—O3—C13—O452.2 (4)
O2—S1—N1—C750.3 (3)Na1iv—O4—C13—C12−59.0 (7)
C1—S1—N1—C7−65.1 (3)Na1iv—O4—C13—O3123.2 (5)
O2—S1—C1—C6−161.3 (3)Na1ii—O7—C26—C21−108.4 (3)
N1—S1—C1—C6−42.6 (4)Na1—O7—C26—O8−33.8 (4)
N1—S1—C1—C2139.5 (3)Na1ii—O7—C26—O872.4 (3)
O1—S1—C1—C2−107.8 (3)Na1—O7—C26—C21145.4 (2)
O2—S1—C1—C220.8 (4)Na2—O8—C26—C2176.0 (5)
O1—S1—C1—C670.2 (4)Na2—O8—C26—O7−104.8 (4)
C14—S2—N2—C2061.3 (4)S1—N1—C7—C12177.4 (2)
O5—S2—N2—C20−55.7 (4)S1—N1—C7—C8−1.4 (5)
O6—S2—N2—C20175.1 (3)S2—N2—C20—C21−167.0 (3)
O5—S2—C14—C19−4.6 (4)S2—N2—C20—C2512.9 (6)
O5—S2—C14—C15176.2 (4)C6—C1—C2—C3−2.2 (7)
O6—S2—C14—C15−55.1 (4)S1—C1—C2—C3175.7 (4)
C14—S2—O6—Na2i−171.6 (4)S1—C1—C6—C5−176.9 (4)
O6—S2—C14—C19124.1 (3)C2—C1—C6—C51.0 (7)
N2—S2—C14—C19−123.6 (4)C1—C2—C3—C42.1 (8)
N2—S2—O6—Na2i74.9 (4)C2—C3—C4—Br1179.5 (4)
O5—S2—O6—Na2i−49.6 (4)C2—C3—C4—C5−0.9 (8)
N2—S2—C14—C1557.2 (4)Br1—C4—C5—C6179.3 (4)
O9ii—Na1ii—O7—C26157.1 (2)C3—C4—C5—C6−0.3 (9)
O7ii—Na1ii—O7—Na10.02 (12)C4—C5—C6—C10.2 (8)
O7ii—Na1—O7—Na1ii−0.02 (11)C12—C7—C8—C92.0 (5)
O4i—Na1—O7—Na1ii93.94 (9)N1—C7—C12—C11176.5 (3)
O9—Na1—O7—Na1ii−78.22 (8)N1—C7—C8—C9−179.2 (3)
O7ii—Na1—O7—C26125.6 (2)C8—C7—C12—C11−4.7 (5)
O4v—Na1ii—O7—Na181.95 (9)C8—C7—C12—C13172.0 (3)
O7iv—Na1iv—O4—C13159.6 (6)N1—C7—C12—C13−6.9 (5)
O9iv—Na1iv—O4—C13−178.2 (5)C7—C8—C9—C102.5 (5)
O1—Na1—O7—Na1ii−164.18 (8)C8—C9—C10—C11−4.1 (5)
O1iii—Na1iii—O2—S133.6 (4)C9—C10—C11—C121.2 (5)
O9iii—Na1iii—O2—S1118.2 (4)C10—C11—C12—C73.2 (5)
O7ii—Na1ii—O7—C26−124.8 (2)C10—C11—C12—C13−173.7 (3)
O4i—Na1—O7—C26−140.4 (2)C11—C12—C13—O3−177.8 (3)
O1iv—Na1iv—O4—C1377.6 (6)C7—C12—C13—O4−172.4 (3)
O4v—Na1ii—O7—C26−42.9 (2)C11—C12—C13—O44.2 (4)
O7v—Na1iv—O4—C13−106.5 (6)C7—C12—C13—O35.6 (5)
O9ii—Na1ii—O7—Na1−78.07 (7)S2—C14—C19—C18−178.3 (4)
O9—Na1—O7—C2647.4 (2)S2—C14—C15—C16178.2 (4)
O1—Na1—O7—C26−38.6 (2)C15—C14—C19—C180.9 (7)
O9—Na2v—O3—C13−164.9 (2)C19—C14—C15—C16−1.0 (7)
O3ii—Na2i—O6—S2−34.1 (6)C14—C15—C16—C170.3 (8)
O6ii—Na2v—O3—Na2114.8 (3)C15—C16—C17—Br2178.5 (4)
O6iv—Na2—O8—C26−104.8 (4)C15—C16—C17—C180.4 (9)
O3v—Na2—O8—C2667.4 (4)C16—C17—C18—C19−0.5 (9)
O3—Na2—O8—C26168.3 (4)Br2—C17—C18—C19−178.5 (4)
O8v—Na2v—O3—Na2−87.84 (9)C17—C18—C19—C14−0.2 (8)
O9—Na2v—O3—Na279.25 (7)C21—C20—C25—C24−2.4 (6)
O3v—Na2v—O3—Na20.00 (8)C25—C20—C21—C220.6 (6)
O3v—Na2—O3—C13−125.8 (2)N2—C20—C21—C22−179.5 (3)
O9v—Na2—O3—C13−48.7 (2)N2—C20—C21—C260.5 (5)
O8—Na2—O3—Na2v−102.82 (8)C25—C20—C21—C26−179.4 (3)
O6iv—Na2—O3—Na2v161.43 (9)N2—C20—C25—C24177.7 (4)
O3v—Na2—O3—Na2v0.00 (8)C26—C21—C22—C23−178.5 (4)
O9v—Na2—O3—Na2v77.13 (8)C20—C21—C22—C231.4 (6)
O3i—Na2i—O6—S2−151.3 (4)C22—C21—C26—O7173.4 (3)
O8i—Na2i—O6—S2123.8 (4)C20—C21—C26—O7−6.5 (5)
O6iv—Na2—O3—C1335.6 (2)C20—C21—C26—O8172.7 (3)
O8v—Na2v—O3—C1328.1 (2)C22—C21—C26—O8−7.3 (5)
O9ii—Na2i—O6—S2−69.2 (4)C21—C22—C23—C24−1.7 (6)
O3v—Na2v—O3—C13115.9 (2)C22—C23—C24—C25−0.1 (7)
O6ii—Na2v—O3—C13−129.3 (3)C23—C24—C25—C202.1 (7)
O8—Na2—O3—C13131.3 (2)
D—H···AD—HH···AD···AD—H···A
N1—H1···O30.861.882.588 (3)138
O9—HW1···O80.849 (19)1.97 (3)2.768 (3)156 (6)
N2—H2···O70.861.902.595 (4)137
O9—HW2···O4v0.86 (4)1.91 (4)2.730 (3)160 (6)
C2—H2A···O20.932.522.886 (4)104
C8—H8···O20.932.553.117 (5)120
C11—H11···O1iv0.932.533.429 (4)162
C11—H11···O40.932.412.732 (5)100
C19—H19···O50.932.512.889 (5)105
C22—H22···O80.932.412.736 (4)101
C25—H25···O50.932.483.103 (5)124
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1⋯O30.861.882.588 (3)138
O9—HW1⋯O80.849 (19)1.97 (3)2.768 (3)156 (6)
N2—H2⋯O70.861.902.595 (4)137
O9—HW2⋯O4i0.86 (4)1.91 (4)2.730 (3)160 (6)
C2—H2A⋯O20.932.522.886 (4)104
C8—H8⋯O20.932.553.117 (5)120
C11—H11⋯O1ii0.932.533.429 (4)162
C11—H11⋯O40.932.412.732 (5)100
C19—H19⋯O50.932.512.889 (5)105
C22—H22⋯O80.932.412.736 (4)101
C25—H25⋯O50.932.483.103 (5)124

Symmetry codes: (i) ; (ii) .

  3 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  2-(4-Bromo-benzene-sulfonamido)benzoic acid.

Authors:  Muhammad Nadeem Arshad; Islam Ullah Khan; Mehmet Akkurt; Muhammad Shafiq; Ghulam Mustafa
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-06-17

3.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  3 in total

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