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The title compound, C24H18N2O4·C2H6OS, adopts an anti C=O conformation. The two amide groups are twisted away from the attached central ring by 48.48 (5) and 46.49 (5)°. In the crystal structure, the mol­ecules are connected by O—H...O and N—H...O hydrogen bonds, forming a two-dimensional network parallel to the (110) plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680603786X/ci2173sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680603786X/ci2173Isup2.hkl
Contains datablock I

CCDC reference: 624180

Key indicators

  • Single-crystal X-ray study
  • T = 153 K
  • Mean [sigma](C-C) = 0.002 Å
  • Disorder in solvent or counterion
  • R factor = 0.033
  • wR factor = 0.096
  • Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C2 H6 O S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXL97.

N,N'-Bis(2-hydroxyphenyl)naphthalene-1,4-dicarboxamide dimethyl sulfoxide solvate top
Crystal data top
C24H18N2O4·C2H6OSZ = 2
Mr = 476.53F(000) = 500
Triclinic, P1Dx = 1.405 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.5769 (3) ÅCell parameters from 9765 reflections
b = 9.6804 (2) Åθ = 3.1–27.5°
c = 13.0811 (3) ŵ = 0.19 mm1
α = 109.796 (1)°T = 153 K
β = 98.157 (1)°Block, colourless
γ = 91.369 (1)°0.33 × 0.18 × 0.16 mm
V = 1126.14 (5) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer
5129 independent reflections
Radiation source: Rotating Anode4544 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.013
ω scansθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1212
Tmin = 0.941, Tmax = 0.971k = 1112
11181 measured reflectionsl = 1616
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)] = 0.033H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.096 w = 1/[σ2(Fo2) + (0.0566P)2 + 0.38P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
5129 reflectionsΔρmax = 0.42 e Å3
353 parametersΔρmin = 0.27 e Å3
6 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0088 (17)
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.

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 > σ(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 (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.12933 (10)1.21450 (9)0.24539 (7)0.02411 (19)
O20.16442 (9)1.03100 (9)0.53205 (7)0.02150 (19)
O30.25559 (9)0.54871 (9)0.04096 (7)0.02131 (18)
O40.49235 (9)0.58363 (9)0.06985 (7)0.02182 (18)
N10.06479 (10)1.12173 (10)0.38117 (8)0.0179 (2)
N20.20762 (10)0.62814 (10)0.10446 (8)0.0180 (2)
C10.00655 (12)1.00242 (12)0.20498 (9)0.0165 (2)
C20.01920 (12)0.86020 (12)0.20009 (9)0.0192 (2)
H20.08360.83910.24280.023*
C30.04892 (12)0.74511 (12)0.13234 (9)0.0190 (2)
H30.02960.64710.12960.023*
C40.14280 (11)0.77244 (12)0.07023 (9)0.0161 (2)
C50.27524 (12)0.95615 (13)0.01514 (9)0.0208 (2)
H50.32670.88090.02730.025*
C60.30004 (14)1.09779 (14)0.01947 (10)0.0252 (3)
H60.36711.11970.02090.030*
C70.22684 (14)1.21151 (13)0.08345 (11)0.0250 (3)
H70.24301.30920.08460.030*
C80.13272 (12)1.18186 (12)0.14388 (10)0.0205 (2)
H80.08671.26020.18890.025*
C90.10219 (11)1.03592 (12)0.14077 (9)0.0158 (2)
C100.17352 (11)0.91949 (12)0.07324 (9)0.0158 (2)
C110.06815 (12)1.12306 (12)0.27771 (9)0.0168 (2)
C120.12465 (11)1.22541 (12)0.46598 (9)0.0167 (2)
C130.13126 (12)1.37267 (13)0.47620 (10)0.0209 (2)
H130.09891.40670.42290.025*
C140.18508 (13)1.47050 (13)0.56405 (10)0.0237 (2)
H140.18881.57120.57080.028*
C150.23327 (13)1.42129 (13)0.64153 (10)0.0236 (2)
H150.27011.48820.70140.028*
C160.22788 (12)1.27439 (13)0.63189 (9)0.0210 (2)
H160.26131.24090.68510.025*
C170.17364 (11)1.17588 (12)0.54451 (9)0.0173 (2)
C180.20933 (11)0.64073 (12)0.00130 (9)0.0167 (2)
C190.26728 (12)0.51183 (12)0.18162 (9)0.0171 (2)
C200.18298 (13)0.42568 (12)0.27903 (10)0.0211 (2)
H200.08630.44370.29300.025*
C210.23913 (15)0.31317 (14)0.35624 (10)0.0271 (3)
H210.18180.25550.42350.033*
C220.37961 (15)0.28611 (14)0.33406 (10)0.0295 (3)
H220.41790.20760.38550.035*
C230.46484 (14)0.37260 (14)0.23744 (10)0.0254 (3)
H230.56080.35250.22300.030*
C240.41053 (12)0.48884 (12)0.16148 (9)0.0182 (2)
H1N0.0191 (17)1.0541 (18)0.3988 (13)0.028 (4)*
H2N0.1655 (17)0.6911 (18)0.1320 (13)0.030 (4)*
H2O0.223 (2)1.005 (2)0.5715 (16)0.045 (5)*
H4O0.572 (2)0.539 (2)0.0560 (17)0.054 (6)*
S0.48221 (4)0.89011 (4)0.61960 (3)0.02848 (13)0.9232 (16)
O50.32832 (14)0.94518 (17)0.64464 (11)0.0420 (3)0.9232 (16)
C250.5484 (3)0.9616 (3)0.7454 (2)0.0399 (4)0.9232 (16)
H25A0.48350.94440.80410.048*0.9232 (16)
H25B0.64170.91230.73820.048*0.9232 (16)
H25C0.55681.06760.76340.048*0.9232 (16)
C260.4817 (2)0.70388 (19)0.6120 (2)0.0497 (6)0.9232 (16)
H26A0.44360.64580.54630.060*0.9232 (16)
H26B0.57870.66510.60780.060*0.9232 (16)
H26C0.42270.69780.67780.060*0.9232 (16)
S'0.4119 (6)0.8838 (7)0.6863 (4)0.0456 (18)0.0768 (16)
O5'0.3889 (17)0.9537 (19)0.6027 (13)0.051 (5)0.0768 (16)
C25'0.546 (3)0.978 (3)0.755 (3)0.0399 (4)0.0768 (16)
H25D0.58130.92270.79830.048*0.0768 (16)
H25E0.62420.98710.70140.048*0.0768 (16)
H25F0.50761.07630.80500.048*0.0768 (16)
C26'0.512 (3)0.715 (2)0.610 (2)0.0497 (6)0.0768 (16)
H26D0.58720.73090.55690.060*0.0768 (16)
H26E0.55510.67790.66070.060*0.0768 (16)
H26F0.45060.64320.57140.060*0.0768 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0323 (5)0.0250 (4)0.0188 (4)0.0139 (3)0.0074 (3)0.0103 (3)
O20.0276 (4)0.0191 (4)0.0220 (4)0.0078 (3)0.0113 (3)0.0092 (3)
O30.0236 (4)0.0228 (4)0.0227 (4)0.0096 (3)0.0084 (3)0.0121 (3)
O40.0199 (4)0.0217 (4)0.0226 (4)0.0030 (3)0.0030 (3)0.0062 (3)
N10.0227 (5)0.0177 (4)0.0159 (5)0.0089 (4)0.0074 (4)0.0070 (4)
N20.0224 (5)0.0177 (4)0.0150 (4)0.0090 (4)0.0052 (4)0.0057 (4)
C10.0187 (5)0.0179 (5)0.0131 (5)0.0052 (4)0.0033 (4)0.0049 (4)
C20.0232 (5)0.0201 (5)0.0171 (5)0.0044 (4)0.0088 (4)0.0078 (4)
C30.0253 (6)0.0155 (5)0.0184 (5)0.0044 (4)0.0065 (4)0.0072 (4)
C40.0183 (5)0.0171 (5)0.0128 (5)0.0053 (4)0.0025 (4)0.0046 (4)
C50.0206 (5)0.0231 (6)0.0174 (5)0.0011 (4)0.0061 (4)0.0040 (4)
C60.0268 (6)0.0267 (6)0.0231 (6)0.0031 (5)0.0099 (5)0.0078 (5)
C70.0306 (6)0.0186 (5)0.0268 (6)0.0019 (5)0.0068 (5)0.0083 (5)
C80.0235 (6)0.0168 (5)0.0203 (6)0.0025 (4)0.0045 (4)0.0049 (4)
C90.0173 (5)0.0174 (5)0.0124 (5)0.0025 (4)0.0019 (4)0.0049 (4)
C100.0165 (5)0.0178 (5)0.0123 (5)0.0023 (4)0.0018 (4)0.0042 (4)
C110.0183 (5)0.0173 (5)0.0155 (5)0.0037 (4)0.0051 (4)0.0052 (4)
C120.0158 (5)0.0183 (5)0.0147 (5)0.0048 (4)0.0035 (4)0.0032 (4)
C130.0226 (6)0.0198 (5)0.0208 (6)0.0035 (4)0.0062 (4)0.0063 (4)
C140.0258 (6)0.0168 (5)0.0267 (6)0.0049 (4)0.0069 (5)0.0038 (4)
C150.0234 (6)0.0232 (6)0.0203 (6)0.0064 (4)0.0076 (4)0.0005 (4)
C160.0213 (5)0.0252 (6)0.0170 (5)0.0057 (4)0.0070 (4)0.0063 (4)
C170.0161 (5)0.0190 (5)0.0162 (5)0.0047 (4)0.0032 (4)0.0049 (4)
C180.0166 (5)0.0169 (5)0.0166 (5)0.0040 (4)0.0042 (4)0.0051 (4)
C190.0228 (5)0.0145 (5)0.0159 (5)0.0057 (4)0.0075 (4)0.0057 (4)
C200.0244 (6)0.0200 (5)0.0189 (5)0.0041 (4)0.0040 (4)0.0061 (4)
C210.0369 (7)0.0222 (6)0.0179 (6)0.0043 (5)0.0036 (5)0.0016 (4)
C220.0410 (8)0.0255 (6)0.0206 (6)0.0137 (5)0.0124 (5)0.0026 (5)
C230.0261 (6)0.0281 (6)0.0242 (6)0.0112 (5)0.0115 (5)0.0083 (5)
C240.0218 (5)0.0179 (5)0.0172 (5)0.0034 (4)0.0069 (4)0.0072 (4)
S0.0255 (2)0.0354 (2)0.0225 (2)0.00184 (14)0.00005 (14)0.00902 (14)
O50.0315 (7)0.0657 (9)0.0330 (7)0.0129 (7)0.0037 (5)0.0241 (6)
C250.0383 (8)0.0474 (11)0.0327 (10)0.0035 (7)0.0116 (7)0.0100 (8)
C260.0327 (12)0.0319 (8)0.0758 (13)0.0048 (8)0.0010 (9)0.0104 (8)
S'0.033 (3)0.062 (4)0.036 (3)0.005 (2)0.006 (2)0.015 (2)
O5'0.021 (8)0.065 (11)0.082 (15)0.002 (8)0.025 (9)0.038 (11)
C25'0.0383 (8)0.0474 (11)0.0327 (10)0.0035 (7)0.0116 (7)0.0100 (8)
C26'0.0327 (12)0.0319 (8)0.0758 (13)0.0048 (8)0.0010 (9)0.0104 (8)
Geometric parameters (Å, º) top
O1—C111.2303 (13)C14—C151.3844 (18)
O2—C171.3625 (14)C14—H140.95
O2—H2O0.90 (2)C15—C161.3874 (17)
O3—C181.2351 (13)C15—H150.95
O4—C241.3590 (14)C16—C171.3926 (15)
O4—H4O0.91 (2)C16—H160.95
N1—C111.3536 (14)C19—C201.3882 (16)
N1—C121.4214 (13)C19—C241.3974 (16)
N1—H1N0.872 (16)C20—C211.3901 (16)
N2—C181.3447 (14)C20—H200.95
N2—C191.4274 (13)C21—C221.3859 (19)
N2—H2N0.886 (16)C21—H210.95
C1—C21.3711 (16)C22—C231.3865 (19)
C1—C91.4277 (15)C22—H220.95
C1—C111.5037 (14)C23—C241.3933 (15)
C2—C31.4080 (15)C23—H230.95
C2—H20.95S—O51.5069 (13)
C3—C41.3711 (16)S—C251.7701 (19)
C3—H30.95S—C261.7719 (19)
C4—C101.4329 (15)C25—H25A0.98
C4—C181.5059 (14)C25—H25B0.98
C5—C61.3666 (17)C25—H25C0.98
C5—C101.4243 (16)C26—H26A0.98
C5—H50.95C26—H26B0.98
C6—C71.4082 (17)C26—H26C0.98
C6—H60.95S'—O5'1.505 (3)
C7—C81.3650 (17)S'—C25'1.770 (4)
C7—H70.95S'—C26'1.771 (4)
C8—C91.4216 (15)C25'—H25D0.98
C8—H80.95C25'—H25E0.98
C9—C101.4321 (14)C25'—H25F0.98
C12—C131.3898 (16)C26'—H26D0.98
C12—C171.4018 (16)C26'—H26E0.98
C13—C141.3920 (16)C26'—H26F0.98
C13—H130.95
C17—O2—H2O109.6 (12)C13—C14—H14120.0
C24—O4—H4O108.0 (13)C14—C15—C16120.08 (10)
C11—N1—C12125.56 (9)C14—C15—H15120.0
C11—N1—H1N117.8 (11)C16—C15—H15120.0
C12—N1—H1N116.5 (11)C15—C16—C17120.22 (11)
C18—N2—C19123.74 (9)C15—C16—H16119.9
C18—N2—H2N121.4 (10)C17—C16—H16119.9
C19—N2—H2N114.8 (10)O2—C17—C16122.51 (10)
C2—C1—C9120.46 (10)O2—C17—C12117.66 (9)
C2—C1—C11119.43 (10)C16—C17—C12119.83 (10)
C9—C1—C11120.10 (9)O3—C18—N2123.76 (10)
C1—C2—C3120.58 (10)O3—C18—C4120.33 (10)
C1—C2—H2119.7N2—C18—C4115.83 (9)
C3—C2—H2119.7C20—C19—C24120.28 (10)
C4—C3—C2120.95 (10)C20—C19—N2119.31 (10)
C4—C3—H3119.5C24—C19—N2120.35 (10)
C2—C3—H3119.5C19—C20—C21120.42 (11)
C3—C4—C10120.38 (9)C19—C20—H20119.8
C3—C4—C18116.15 (9)C21—C20—H20119.8
C10—C4—C18123.47 (10)C22—C21—C20119.28 (12)
C6—C5—C10121.08 (10)C22—C21—H21120.4
C6—C5—H5119.5C20—C21—H21120.4
C10—C5—H5119.5C21—C22—C23120.62 (11)
C5—C6—C7120.43 (11)C21—C22—H22119.7
C5—C6—H6119.8C23—C22—H22119.7
C7—C6—H6119.8C22—C23—C24120.37 (11)
C8—C7—C6120.27 (11)C22—C23—H23119.8
C8—C7—H7119.9C24—C23—H23119.8
C6—C7—H7119.9O4—C24—C23122.55 (11)
C7—C8—C9121.23 (10)O4—C24—C19118.51 (10)
C7—C8—H8119.4C23—C24—C19118.91 (11)
C9—C8—H8119.4O5—S—C25105.92 (12)
C8—C9—C1122.34 (10)O5—S—C26104.86 (9)
C8—C9—C10118.54 (10)C25—S—C2697.75 (11)
C1—C9—C10119.09 (9)O5'—S'—C25'106.1 (4)
C5—C10—C9118.36 (10)O5'—S'—C26'105.2 (4)
C5—C10—C4123.09 (10)C25'—S'—C26'97.9 (4)
C9—C10—C4118.51 (10)S'—C25'—H25D109.5
O1—C11—N1122.57 (10)S'—C25'—H25E109.5
O1—C11—C1122.73 (10)H25D—C25'—H25E109.5
N1—C11—C1114.69 (9)S'—C25'—H25F109.5
C13—C12—C17119.43 (10)H25D—C25'—H25F109.5
C13—C12—N1123.01 (10)H25E—C25'—H25F109.5
C17—C12—N1117.51 (10)S'—C26'—H26D109.5
C12—C13—C14120.36 (11)S'—C26'—H26E109.5
C12—C13—H13119.8H26D—C26'—H26E109.5
C14—C13—H13119.8S'—C26'—H26F109.5
C15—C14—C13120.08 (11)H26D—C26'—H26F109.5
C15—C14—H14120.0H26E—C26'—H26F109.5
C9—C1—C2—C30.44 (17)C11—N1—C12—C17149.66 (11)
C11—C1—C2—C3179.75 (10)C17—C12—C13—C140.46 (17)
C1—C2—C3—C40.31 (18)N1—C12—C13—C14176.95 (11)
C2—C3—C4—C100.05 (17)C12—C13—C14—C150.41 (19)
C2—C3—C4—C18179.82 (10)C13—C14—C15—C160.08 (19)
C10—C5—C6—C71.14 (19)C14—C15—C16—C170.20 (18)
C5—C6—C7—C81.5 (2)C15—C16—C17—O2179.17 (11)
C6—C7—C8—C92.37 (19)C15—C16—C17—C120.14 (17)
C7—C8—C9—C1178.61 (11)C13—C12—C17—O2179.54 (10)
C7—C8—C9—C100.55 (17)N1—C12—C17—O21.98 (15)
C2—C1—C9—C8179.56 (11)C13—C12—C17—C160.19 (17)
C11—C1—C9—C81.14 (16)N1—C12—C17—C16177.37 (10)
C2—C1—C9—C101.52 (16)C19—N2—C18—O34.20 (18)
C11—C1—C9—C10179.18 (9)C19—N2—C18—C4179.12 (10)
C6—C5—C10—C92.89 (17)C3—C4—C18—O345.12 (15)
C6—C5—C10—C4179.30 (11)C10—C4—C18—O3134.65 (11)
C8—C9—C10—C52.03 (15)C3—C4—C18—N2131.69 (11)
C1—C9—C10—C5176.08 (10)C10—C4—C18—N248.55 (15)
C8—C9—C10—C4179.94 (10)C18—N2—C19—C20124.29 (12)
C1—C9—C10—C41.83 (15)C18—N2—C19—C2458.38 (15)
C3—C4—C10—C5176.69 (11)C24—C19—C20—C211.70 (17)
C18—C4—C10—C53.07 (17)N2—C19—C20—C21179.03 (10)
C3—C4—C10—C91.12 (16)C19—C20—C21—C221.18 (19)
C18—C4—C10—C9179.13 (10)C20—C21—C22—C231.8 (2)
C12—N1—C11—O12.47 (18)C21—C22—C23—C240.4 (2)
C12—N1—C11—C1178.56 (10)C22—C23—C24—O4174.78 (11)
C2—C1—C11—O1131.02 (12)C22—C23—C24—C193.28 (18)
C9—C1—C11—O148.29 (16)C20—C19—C24—O4174.23 (10)
C2—C1—C11—N147.95 (15)N2—C19—C24—O43.07 (16)
C9—C1—C11—N1132.74 (11)C20—C19—C24—C233.91 (17)
C11—N1—C12—C1332.88 (17)N2—C19—C24—C23178.79 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.872 (16)2.170 (17)2.9796 (12)154 (1)
N2—H2N···O1ii0.886 (16)1.985 (17)2.8010 (12)153 (2)
O2—H2O···O50.90 (2)1.70 (2)2.5972 (15)176 (2)
O2—H2O···O50.90 (2)1.80 (2)2.644 (12)157 (2)
O4—H4O···O3iii0.91 (2)1.89 (2)2.7978 (12)174 (2)
O4—H4O···O4iii0.91 (2)2.47 (2)2.8146 (17)103 (2)
C7—H7···O3iv0.952.573.5029 (14)166
Symmetry codes: (i) x, y+2, z+1; (ii) x, y+2, z; (iii) x+1, y+1, z; (iv) x, y+1, z.
 

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