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The molecule of the title salt, C26H22OP+.C4H3O4, consists of a benzoyl­methyl­tri­phenyl­phospho­nium cation (HBPPY) and a hydrogen maleate anion. Owing to a strong O—H...O intraionic hydrogen bond, each hydrogen maleate ion forms a ring, described by the graph-set notation S11(7). Several C—H...O interactions are present between the cations and anions and contribute to the stabilization of the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803029404/ob6335sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803029404/ob6335Isup2.hkl
Contains datablock I

CCDC reference: 234845

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.041
  • wR factor = 0.106
  • Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.820 0.975 Tmin' and Tmax expected: 0.949 0.975 RR' = 0.864 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.86
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Benzoylmethyltriphenylphosphonium hydrogenmaleate top
Crystal data top
C26H22OP+·C4H3O4Dx = 1.328 Mg m3
Mr = 496.47Melting point: 413 K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 973 reflections
a = 10.5582 (5) Åθ = 2.3–27.0°
b = 19.5961 (8) ŵ = 0.15 mm1
c = 24.0030 (11) ÅT = 120 K
V = 4966.2 (4) Å3Block, colourless
Z = 80.34 × 0.29 × 0.17 mm
F(000) = 2080
Data collection top
Bruker SMART CCD 6K area-detector
diffractometer
5704 independent reflections
Radiation source: fine-focus sealed tube4255 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
Detector resolution: 8 pixels mm-1θmax = 27.5°, θmin = 1.7°
ω scansh = 1311
Absorption correction: multi-scan
(SADABS; Sheldrick, 1998)
k = 2523
Tmin = 0.820, Tmax = 0.975l = 3130
36772 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: difference Fourier map
wR(F2) = 0.106All H-atom parameters refined
S = 1.01 w = 1/[σ2(Fo2) + (0.0326P)2 + 2.7423P]
where P = (Fo2 + 2Fc2)/3
5704 reflections(Δ/σ)max < 0.001
425 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.26 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.

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*/Ueq
P10.07926 (4)0.08182 (2)0.668013 (17)0.02209 (11)
C10.12537 (15)0.05703 (8)0.79639 (7)0.0244 (3)
C20.20776 (17)0.05985 (10)0.84150 (8)0.0346 (4)
H20.277 (2)0.0297 (11)0.8435 (9)0.051 (6)*
C30.18939 (18)0.10682 (11)0.88364 (8)0.0387 (4)
H30.246 (2)0.1095 (10)0.9141 (9)0.041 (6)*
C40.08858 (19)0.15212 (9)0.88077 (8)0.0367 (4)
H40.0750 (18)0.1864 (9)0.9096 (8)0.034 (5)*
C50.0062 (2)0.14953 (10)0.83594 (8)0.0382 (4)
H50.067 (2)0.1793 (11)0.8332 (10)0.052 (6)*
C60.02354 (17)0.10196 (9)0.79383 (8)0.0316 (4)
H60.0353 (18)0.1012 (9)0.7623 (8)0.032 (5)*
C70.14983 (14)0.00508 (8)0.75298 (7)0.0233 (3)
C80.05025 (15)0.00587 (8)0.70838 (7)0.0225 (3)
H8A0.0353 (18)0.0105 (9)0.7243 (8)0.030 (5)*
H8B0.047 (2)0.0345 (11)0.6831 (9)0.046 (6)*
C90.05591 (15)0.09462 (8)0.62374 (7)0.0272 (4)
C100.0781 (2)0.04718 (10)0.58145 (8)0.0390 (4)
H100.023 (2)0.0102 (11)0.5773 (9)0.043 (6)*
C110.1790 (2)0.05661 (12)0.54539 (10)0.0482 (5)
H110.192 (2)0.0248 (12)0.5178 (10)0.053 (7)*
C120.25651 (19)0.11300 (12)0.55126 (9)0.0484 (6)
H120.325 (2)0.1194 (11)0.5241 (10)0.050 (6)*
C130.2350 (2)0.15959 (13)0.59294 (10)0.0508 (6)
H130.290 (2)0.1981 (12)0.5972 (11)0.065 (7)*
C140.13463 (18)0.15106 (11)0.62964 (8)0.0386 (4)
H140.119 (2)0.1856 (12)0.6584 (10)0.055 (7)*
C150.09654 (15)0.15199 (8)0.71576 (7)0.0259 (3)
C160.01554 (18)0.15627 (10)0.76133 (9)0.0378 (4)
H160.051 (2)0.1243 (10)0.7644 (9)0.044 (6)*
C170.03165 (19)0.20852 (11)0.79980 (10)0.0444 (5)
H170.023 (2)0.2102 (12)0.8326 (11)0.061 (7)*
C180.12595 (19)0.25625 (10)0.79270 (9)0.0388 (4)
H180.1354 (19)0.2917 (10)0.8194 (9)0.041 (6)*
C190.20586 (19)0.25250 (9)0.74757 (9)0.0376 (4)
H190.269 (2)0.2850 (11)0.7412 (10)0.056 (7)*
C200.19149 (17)0.20035 (9)0.70861 (8)0.0311 (4)
H200.249 (2)0.1979 (10)0.6772 (9)0.036 (5)*
C210.21235 (14)0.07272 (8)0.62209 (7)0.0249 (3)
C220.22264 (18)0.11835 (9)0.57764 (7)0.0314 (4)
H220.1616 (19)0.1536 (10)0.5732 (8)0.038 (5)*
C230.3218 (2)0.11160 (9)0.53999 (8)0.0376 (4)
H230.326 (2)0.1429 (11)0.5081 (9)0.048 (6)*
C240.40862 (18)0.05970 (10)0.54626 (8)0.0379 (4)
H240.477 (2)0.0556 (11)0.5197 (10)0.048 (6)*
C250.39807 (18)0.01380 (11)0.58970 (8)0.0390 (4)
H250.458 (2)0.0218 (11)0.5930 (9)0.046 (6)*
C260.29967 (16)0.01984 (9)0.62795 (8)0.0328 (4)
H260.2923 (18)0.0142 (10)0.6578 (8)0.034 (5)*
C271.00604 (18)0.21784 (9)0.48101 (8)0.0376 (4)
C280.87176 (18)0.21626 (9)0.46199 (8)0.0326 (4)
H280.8221 (18)0.2422 (10)0.4850 (9)0.038 (5)*
C290.81817 (18)0.18673 (9)0.41798 (8)0.0325 (4)
H290.729 (2)0.1930 (10)0.4135 (9)0.042 (6)*
C300.87435 (17)0.14243 (9)0.37351 (8)0.0314 (4)
O10.24667 (11)0.02886 (6)0.75232 (5)0.0298 (3)
O21.08911 (13)0.18012 (8)0.45561 (7)0.0507 (4)
H11.043 (3)0.1521 (16)0.4232 (14)0.097 (10)*
O31.03557 (14)0.25455 (8)0.51998 (7)0.0559 (4)
O40.80859 (13)0.12865 (7)0.33260 (6)0.0406 (3)
O50.98781 (12)0.11955 (7)0.37990 (6)0.0417 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.01906 (19)0.0239 (2)0.0233 (2)0.00029 (15)0.00039 (15)0.00196 (16)
C10.0225 (8)0.0283 (8)0.0222 (8)0.0032 (6)0.0021 (6)0.0011 (6)
C20.0220 (8)0.0507 (11)0.0312 (10)0.0017 (8)0.0007 (7)0.0101 (8)
C30.0275 (9)0.0593 (12)0.0293 (10)0.0064 (8)0.0013 (8)0.0140 (9)
C40.0443 (11)0.0348 (9)0.0308 (10)0.0081 (8)0.0082 (8)0.0100 (8)
C50.0470 (11)0.0340 (9)0.0336 (10)0.0104 (8)0.0032 (9)0.0030 (8)
C60.0349 (10)0.0330 (9)0.0268 (9)0.0054 (7)0.0026 (7)0.0011 (7)
C70.0210 (8)0.0266 (8)0.0225 (8)0.0026 (6)0.0010 (6)0.0001 (6)
C80.0214 (8)0.0247 (8)0.0215 (8)0.0005 (6)0.0003 (6)0.0026 (6)
C90.0217 (8)0.0327 (8)0.0271 (9)0.0035 (6)0.0025 (6)0.0081 (7)
C100.0409 (11)0.0348 (10)0.0413 (11)0.0043 (8)0.0135 (9)0.0052 (8)
C110.0517 (13)0.0474 (12)0.0453 (13)0.0188 (10)0.0207 (10)0.0093 (10)
C120.0281 (10)0.0718 (15)0.0453 (13)0.0107 (10)0.0102 (9)0.0245 (11)
C130.0311 (11)0.0746 (15)0.0465 (13)0.0174 (11)0.0031 (9)0.0132 (11)
C140.0308 (10)0.0502 (11)0.0347 (10)0.0111 (8)0.0017 (8)0.0032 (9)
C150.0234 (8)0.0247 (8)0.0298 (9)0.0038 (6)0.0023 (6)0.0001 (6)
C160.0277 (9)0.0428 (10)0.0430 (11)0.0047 (8)0.0067 (8)0.0121 (9)
C170.0342 (10)0.0521 (12)0.0470 (13)0.0008 (9)0.0056 (9)0.0179 (10)
C180.0402 (11)0.0329 (9)0.0432 (11)0.0053 (8)0.0106 (9)0.0099 (9)
C190.0431 (11)0.0286 (9)0.0411 (11)0.0060 (8)0.0111 (9)0.0033 (8)
C200.0304 (9)0.0316 (9)0.0313 (10)0.0016 (7)0.0034 (7)0.0043 (7)
C210.0228 (8)0.0290 (8)0.0229 (8)0.0032 (6)0.0015 (6)0.0007 (6)
C220.0396 (10)0.0276 (8)0.0270 (9)0.0007 (7)0.0025 (7)0.0010 (7)
C230.0525 (12)0.0304 (9)0.0298 (10)0.0083 (8)0.0121 (8)0.0004 (8)
C240.0358 (10)0.0434 (10)0.0344 (10)0.0098 (8)0.0135 (8)0.0096 (8)
C250.0288 (10)0.0477 (11)0.0405 (11)0.0071 (8)0.0049 (8)0.0027 (9)
C260.0275 (9)0.0381 (10)0.0328 (10)0.0054 (7)0.0034 (7)0.0046 (8)
C270.0376 (10)0.0373 (10)0.0378 (10)0.0019 (8)0.0044 (8)0.0075 (8)
C280.0341 (9)0.0279 (9)0.0358 (10)0.0047 (7)0.0089 (8)0.0015 (7)
C290.0293 (9)0.0313 (9)0.0369 (10)0.0054 (7)0.0071 (7)0.0024 (7)
C300.0352 (9)0.0275 (8)0.0316 (10)0.0017 (7)0.0051 (8)0.0033 (7)
O10.0219 (6)0.0354 (6)0.0320 (6)0.0043 (5)0.0018 (5)0.0051 (5)
O20.0348 (8)0.0650 (10)0.0525 (9)0.0128 (7)0.0034 (6)0.0270 (8)
O30.0452 (9)0.0655 (10)0.0571 (10)0.0014 (7)0.0001 (7)0.0298 (8)
O40.0445 (8)0.0421 (7)0.0353 (8)0.0059 (6)0.0030 (6)0.0025 (6)
O50.0350 (7)0.0455 (8)0.0446 (8)0.0121 (6)0.0007 (6)0.0152 (6)
Geometric parameters (Å, º) top
P1—C211.7949 (16)C15—C161.391 (3)
P1—C91.7970 (16)C16—C171.389 (3)
P1—C151.7993 (17)C16—H160.95 (2)
P1—C81.8020 (16)C17—C181.377 (3)
C1—C21.390 (2)C17—H170.98 (3)
C1—C61.391 (2)C18—C191.375 (3)
C1—C71.480 (2)C18—H180.95 (2)
C2—C31.381 (3)C19—C201.394 (3)
C2—H20.94 (2)C19—H190.93 (2)
C3—C41.388 (3)C20—H200.97 (2)
C3—H30.94 (2)C21—C261.394 (2)
C4—C51.385 (3)C21—C221.396 (2)
C4—H40.98 (2)C22—C231.389 (3)
C5—C61.387 (3)C22—H220.95 (2)
C5—H50.97 (2)C23—C241.378 (3)
C6—H60.98 (2)C23—H230.98 (2)
C7—O11.2198 (19)C24—C251.382 (3)
C7—C81.516 (2)C24—H240.96 (2)
C8—H8A0.984 (19)C25—C261.391 (3)
C8—H8B1.00 (2)C25—H250.95 (2)
C9—C141.391 (3)C26—H260.98 (2)
C9—C101.396 (3)C27—O31.221 (2)
C10—C111.385 (3)C27—O21.299 (2)
C10—H100.93 (2)C27—C281.490 (3)
C11—C121.382 (3)C28—C291.331 (3)
C11—H110.92 (2)C28—H280.92 (2)
C12—C131.373 (3)C29—C301.498 (2)
C12—H120.98 (2)C29—H290.96 (2)
C13—C141.388 (3)C30—O41.233 (2)
C13—H130.96 (2)C30—O51.288 (2)
C14—H140.98 (2)O2—H11.07 (3)
C15—C201.390 (2)
C21—P1—C9105.81 (8)C9—C14—H14121.4 (14)
C21—P1—C15112.81 (8)C20—C15—C16119.96 (16)
C9—P1—C15110.52 (8)C20—C15—P1121.03 (13)
C21—P1—C8112.41 (8)C16—C15—P1118.98 (13)
C9—P1—C8107.36 (7)C17—C16—C15119.46 (18)
C15—P1—C8107.81 (8)C17—C16—H16121.8 (13)
C2—C1—C6119.54 (16)C15—C16—H16118.7 (13)
C2—C1—C7117.82 (15)C18—C17—C16120.46 (19)
C6—C1—C7122.64 (15)C18—C17—H17120.3 (14)
C3—C2—C1120.60 (18)C16—C17—H17119.2 (14)
C3—C2—H2119.4 (14)C19—C18—C17120.33 (18)
C1—C2—H2120.0 (14)C19—C18—H18120.4 (13)
C2—C3—C4119.84 (18)C17—C18—H18119.3 (13)
C2—C3—H3121.1 (13)C18—C19—C20120.07 (18)
C4—C3—H3119.1 (13)C18—C19—H19122.0 (14)
C5—C4—C3119.81 (17)C20—C19—H19117.9 (15)
C5—C4—H4119.0 (12)C15—C20—C19119.71 (18)
C3—C4—H4121.2 (12)C15—C20—H20120.8 (12)
C4—C5—C6120.52 (18)C19—C20—H20119.5 (12)
C4—C5—H5122.0 (14)C26—C21—C22120.11 (16)
C6—C5—H5117.4 (14)C26—C21—P1121.98 (13)
C5—C6—C1119.69 (17)C22—C21—P1117.81 (13)
C5—C6—H6119.3 (11)C23—C22—C21119.65 (17)
C1—C6—H6121.0 (11)C23—C22—H22120.4 (12)
O1—C7—C1122.05 (14)C21—C22—H22119.9 (12)
O1—C7—C8119.67 (14)C24—C23—C22120.05 (18)
C1—C7—C8118.28 (13)C24—C23—H23121.0 (13)
C7—C8—P1112.26 (11)C22—C23—H23118.9 (13)
C7—C8—H8A112.1 (11)C23—C24—C25120.63 (17)
P1—C8—H8A106.7 (10)C23—C24—H24119.1 (13)
C7—C8—H8B109.8 (12)C25—C24—H24120.3 (13)
P1—C8—H8B109.4 (12)C24—C25—C26120.18 (18)
H8A—C8—H8B106.4 (16)C24—C25—H25119.3 (13)
C14—C9—C10120.22 (17)C26—C25—H25120.5 (13)
C14—C9—P1121.70 (14)C25—C26—C21119.37 (17)
C10—C9—P1118.05 (13)C25—C26—H26118.9 (11)
C11—C10—C9119.6 (2)C21—C26—H26121.7 (11)
C11—C10—H10120.9 (13)O3—C27—O2121.51 (19)
C9—C10—H10119.5 (13)O3—C27—C28119.36 (17)
C12—C11—C10119.9 (2)O2—C27—C28119.13 (17)
C12—C11—H11122.0 (14)C29—C28—C27131.07 (17)
C10—C11—H11118.2 (14)C29—C28—H28118.5 (13)
C13—C12—C11120.54 (19)C27—C28—H28110.4 (12)
C13—C12—H12121.4 (13)C28—C29—C30130.47 (18)
C11—C12—H12118.0 (13)C28—C29—H29116.8 (12)
C12—C13—C14120.5 (2)C30—C29—H29112.7 (12)
C12—C13—H13120.1 (15)O4—C30—O5122.85 (17)
C14—C13—H13119.3 (16)O4—C30—C29118.13 (17)
C13—C14—C9119.2 (2)O5—C30—C29119.02 (16)
C13—C14—H14119.4 (14)C27—O2—H1109.1 (17)
C6—C1—C2—C30.1 (3)C9—P1—C15—C20106.19 (14)
C7—C1—C2—C3179.44 (17)C8—P1—C15—C20136.75 (14)
C1—C2—C3—C40.6 (3)C21—P1—C15—C16166.01 (14)
C2—C3—C4—C50.6 (3)C9—P1—C15—C1675.76 (16)
C3—C4—C5—C60.0 (3)C8—P1—C15—C1641.29 (16)
C4—C5—C6—C10.7 (3)C20—C15—C16—C170.9 (3)
C2—C1—C6—C50.7 (3)P1—C15—C16—C17177.15 (16)
C7—C1—C6—C5179.92 (16)C15—C16—C17—C180.8 (3)
C2—C1—C7—O19.0 (2)C16—C17—C18—C190.4 (3)
C6—C1—C7—O1171.66 (16)C17—C18—C19—C200.2 (3)
C2—C1—C7—C8170.76 (15)C16—C15—C20—C190.7 (3)
C6—C1—C7—C88.6 (2)P1—C15—C20—C19177.30 (14)
O1—C7—C8—P111.78 (19)C18—C19—C20—C150.4 (3)
C1—C7—C8—P1167.98 (11)C9—P1—C21—C26131.84 (15)
C21—P1—C8—C771.77 (13)C15—P1—C21—C26107.21 (15)
C9—P1—C8—C7172.28 (11)C8—P1—C21—C2614.96 (17)
C15—P1—C8—C753.19 (13)C9—P1—C21—C2244.54 (15)
C21—P1—C9—C14124.73 (15)C15—P1—C21—C2276.41 (15)
C15—P1—C9—C142.30 (17)C8—P1—C21—C22161.42 (13)
C8—P1—C9—C14115.04 (15)C26—C21—C22—C231.3 (3)
C21—P1—C9—C1053.15 (16)P1—C21—C22—C23177.76 (14)
C15—P1—C9—C10175.57 (14)C21—C22—C23—C240.6 (3)
C8—P1—C9—C1067.09 (16)C22—C23—C24—C250.2 (3)
C14—C9—C10—C110.0 (3)C23—C24—C25—C260.4 (3)
P1—C9—C10—C11177.92 (16)C24—C25—C26—C210.2 (3)
C9—C10—C11—C120.4 (3)C22—C21—C26—C251.1 (3)
C10—C11—C12—C130.6 (3)P1—C21—C26—C25177.40 (14)
C11—C12—C13—C140.4 (3)O3—C27—C28—C29172.3 (2)
C12—C13—C14—C90.1 (3)O2—C27—C28—C297.6 (3)
C10—C9—C14—C130.1 (3)C27—C28—C29—C302.7 (3)
P1—C9—C14—C13177.68 (16)C28—C29—C30—O4170.25 (19)
C21—P1—C15—C2012.04 (16)C28—C29—C30—O510.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O2i0.94 (2)2.44 (2)3.243 (2)143.0 (16)
C4—H4···O3ii0.98 (2)2.36 (2)3.277 (2)156.8 (16)
C8—H8A···O1iii0.984 (19)2.397 (19)3.371 (2)170.3 (15)
C8—H8B···O4iv1.00 (2)2.42 (2)3.184 (2)132.9 (16)
C8—H8B···O5iv1.00 (2)2.28 (2)3.270 (2)171.0 (17)
C26—H26···O4iv0.98 (2)2.494 (19)3.267 (2)135.4 (15)
C19—H19···O4v0.93 (2)2.49 (2)3.210 (2)134.8 (19)
C26—H26···O10.98 (2)2.47 (2)3.042 (2)117.1 (14)
O2—H1···O51.07 (3)1.35 (3)2.4197 (19)176 (3)
Symmetry codes: (i) x+3/2, y, z+1/2; (ii) x+1, y1/2, z+3/2; (iii) x1/2, y, z+3/2; (iv) x+1, y, z+1; (v) x1/2, y+1/2, z+1.
 

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