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Atenolol, 4-(3-isopropyl­amino­methyl-2-hydroxy­prop­oxy)­phenyl­acetamide, crystallizes as a hydrated succinate salt, 2C14H23N2O3+·C4H4O42-·2H2O. It is isostructural with its fumarate salt. The carboxylic acid transfers its acid H atoms to two mol­ecules of atenolol; the cation, anion and water mol­ecule are linked through hydrogen bonds into a three-dimensional network motif. The succinate anion is located on an inversion center.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806040347/om2054sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806040347/om2054Isup2.hkl
Contains datablock I

CCDC reference: 251175

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.045
  • wR factor = 0.126
  • Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C4 H4 O4 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 H2 O
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C32 H54 N4 O12 Atom count from _chemical_formula_moiety:C28 H46 N4 O6
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 4 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: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.

Bis[(4-acetamidophenoxy-2-hydroxylpropyl)isopropylammonium] succinate dihydrate top
Crystal data top
2C14H23N2O3+·C4H4O42·2H2OF(000) = 740
Mr = 686.79Dx = 1.263 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 780 reflections
a = 11.677 (2) Åθ = 2.8–27.6°
b = 9.377 (1) ŵ = 0.10 mm1
c = 17.225 (2) ÅT = 295 K
β = 106.682 (3)°Block, colorless
V = 1806.6 (4) Å30.50 × 0.20 × 0.16 mm
Z = 2
Data collection top
Bruker SMART 1K area-detector
diffractometer
2498 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.028
Graphite monochromatorθmax = 27.5°, θmin = 2.5°
φ and ω scansh = 1512
11319 measured reflectionsk = 1211
4126 independent reflectionsl = 2222
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0582P)2 + 0.1974P]
where P = (Fo2 + 2Fc2)/3
4126 reflections(Δ/σ)max < 0.001
245 parametersΔρmax = 0.22 e Å3
7 restraintsΔρmin = 0.14 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
O10.58609 (15)1.21190 (15)0.73748 (10)0.0717 (5)
O20.89722 (11)0.76264 (14)0.57228 (8)0.0542 (4)
O31.06272 (10)0.66009 (14)0.49992 (7)0.0426 (3)
H3O1.1249 (13)0.637 (2)0.4846 (12)0.065 (6)*
O40.75356 (11)1.39729 (13)0.55153 (7)0.0456 (3)
O50.65756 (11)1.47625 (17)0.43012 (7)0.0607 (4)
O60.78218 (17)1.3904 (2)0.72321 (11)0.0821 (5)
H6a0.731 (2)1.331 (2)0.7286 (18)0.111 (12)*
H6B0.774 (3)1.400 (3)0.6725 (7)0.105 (10)*
N10.51664 (16)1.00386 (19)0.76707 (10)0.0491 (4)
H1c0.4809 (18)0.9254 (15)0.7524 (13)0.066 (7)*
H1D0.5464 (18)1.018 (2)0.8178 (6)0.067 (7)*
N21.14239 (13)0.45027 (17)0.61397 (9)0.0391 (4)
H2C1.0896 (14)0.4157 (19)0.5721 (8)0.051 (6)*
H2D1.2063 (11)0.4729 (18)0.5990 (10)0.041 (5)*
C10.53720 (17)1.0965 (2)0.71532 (11)0.0437 (4)
C20.50215 (18)1.0524 (2)0.62752 (11)0.0531 (5)
H2A0.47961.13580.59320.064*
H2B0.43400.98860.61640.064*
C30.60692 (16)0.97788 (19)0.60926 (10)0.0416 (4)
C40.61705 (17)0.8316 (2)0.61357 (11)0.0468 (5)
H40.55660.77790.62450.056*
C50.71535 (16)0.7635 (2)0.60188 (12)0.0483 (5)
H50.72100.66460.60540.058*
C60.80487 (16)0.84124 (19)0.58509 (11)0.0414 (4)
C70.79685 (19)0.9879 (2)0.58056 (13)0.0547 (5)
H70.85751.04150.56970.066*
C80.69688 (19)1.0544 (2)0.59247 (12)0.0550 (5)
H80.69091.15330.58890.066*
C91.01344 (15)0.8242 (2)0.59055 (11)0.0444 (4)
H9A1.03720.86150.64540.053*
H9B1.01460.90140.55330.053*
C101.09645 (15)0.7061 (2)0.58174 (10)0.0419 (4)
H101.17820.74350.59550.050*
C111.09255 (18)0.5833 (2)0.63835 (11)0.0479 (5)
H11A1.13800.60860.69310.058*
H11B1.01040.56680.63810.058*
C121.17350 (16)0.3349 (2)0.67751 (11)0.0454 (5)
H121.23080.37380.72610.055*
C131.06418 (18)0.2854 (3)0.69984 (13)0.0620 (6)
H13A1.08670.21340.74110.093*
H13B1.00730.24650.65280.093*
H13C1.02900.36460.71990.093*
C141.2327 (2)0.2152 (3)0.64573 (16)0.0761 (7)
H14A1.25380.14080.68560.114*
H14B1.30350.25000.63440.114*
H14C1.17860.17830.59690.114*
C150.54743 (14)1.45125 (18)0.52570 (10)0.0370 (4)
H15A0.51391.35630.52420.044*
H15B0.56781.48420.58140.044*
C160.66113 (15)1.44139 (17)0.50039 (10)0.0338 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0906 (12)0.0457 (8)0.0963 (12)0.0088 (8)0.0548 (10)0.0083 (8)
O20.0338 (7)0.0494 (8)0.0813 (10)0.0034 (6)0.0195 (7)0.0200 (7)
O30.0288 (7)0.0648 (8)0.0364 (7)0.0074 (6)0.0127 (5)0.0031 (6)
O40.0317 (7)0.0642 (8)0.0436 (7)0.0123 (6)0.0151 (6)0.0088 (6)
O50.0335 (7)0.1165 (12)0.0370 (7)0.0126 (8)0.0180 (6)0.0169 (7)
O60.0634 (11)0.1238 (16)0.0567 (11)0.0125 (11)0.0135 (9)0.0046 (11)
N10.0545 (11)0.0511 (10)0.0434 (10)0.0065 (9)0.0166 (9)0.0018 (8)
N20.0263 (8)0.0577 (9)0.0352 (8)0.0086 (7)0.0120 (7)0.0041 (7)
C10.0404 (10)0.0433 (10)0.0547 (11)0.0120 (9)0.0251 (9)0.0025 (9)
C20.0479 (12)0.0686 (13)0.0461 (11)0.0241 (10)0.0186 (9)0.0093 (10)
C30.0396 (10)0.0521 (11)0.0339 (9)0.0139 (9)0.0115 (8)0.0024 (8)
C40.0395 (11)0.0496 (11)0.0534 (12)0.0014 (9)0.0164 (9)0.0095 (9)
C50.0433 (11)0.0384 (10)0.0627 (12)0.0009 (9)0.0146 (9)0.0102 (9)
C60.0360 (10)0.0440 (10)0.0438 (10)0.0081 (8)0.0107 (8)0.0095 (8)
C70.0543 (13)0.0474 (11)0.0747 (14)0.0006 (10)0.0385 (11)0.0021 (10)
C80.0670 (14)0.0406 (10)0.0690 (14)0.0148 (10)0.0382 (12)0.0078 (9)
C90.0362 (10)0.0491 (11)0.0500 (11)0.0032 (8)0.0161 (8)0.0085 (9)
C100.0304 (9)0.0570 (11)0.0391 (10)0.0029 (8)0.0113 (8)0.0041 (8)
C110.0471 (11)0.0607 (12)0.0405 (10)0.0123 (9)0.0199 (9)0.0009 (9)
C120.0333 (10)0.0622 (12)0.0384 (10)0.0077 (9)0.0065 (8)0.0126 (9)
C130.0510 (13)0.0859 (16)0.0515 (12)0.0017 (12)0.0184 (10)0.0184 (11)
C140.0791 (17)0.0716 (15)0.0856 (17)0.0329 (14)0.0366 (14)0.0300 (13)
C150.0272 (9)0.0487 (10)0.0392 (9)0.0009 (8)0.0164 (7)0.0049 (8)
C160.0291 (9)0.0394 (9)0.0353 (9)0.0005 (7)0.0130 (7)0.0006 (7)
Geometric parameters (Å, º) top
O1—C11.232 (2)C5—H50.9300
O2—C61.375 (2)C6—C71.379 (3)
O2—C91.424 (2)C7—C81.390 (3)
O3—C101.418 (2)C7—H70.9300
O3—H3O0.867 (9)C8—H80.9300
O4—C161.251 (2)C9—C101.508 (2)
O5—C161.2430 (19)C9—H9A0.9700
O6—H6a0.847 (10)C9—H9B0.9700
O6—H6B0.854 (10)C10—C111.518 (3)
N1—C11.315 (2)C10—H100.9800
N1—H1c0.853 (9)C11—H11A0.9700
N1—H1D0.848 (10)C11—H11B0.9700
N2—C111.487 (2)C12—C141.501 (3)
N2—C121.507 (2)C12—C131.509 (2)
N2—H2C0.866 (9)C12—H120.9800
N2—H2D0.883 (9)C13—H13A0.9600
C1—C21.507 (3)C13—H13B0.9600
C2—C31.518 (2)C13—H13C0.9600
C2—H2A0.9700C14—H14A0.9600
C2—H2B0.9700C14—H14B0.9600
C3—C81.370 (3)C14—H14C0.9600
C3—C41.377 (3)C15—C15i1.511 (3)
C4—C51.378 (2)C15—C161.514 (2)
C4—H40.9300C15—H15A0.9700
C5—C61.372 (2)C15—H15B0.9700
C6—O2—C9119.25 (14)O2—C9—H9B110.5
C10—O3—H3O111.1 (14)C10—C9—H9B110.5
H6a—O6—H6b108 (3)H9A—C9—H9B108.7
C1—N1—H1C122.8 (15)O3—C10—C9108.70 (14)
C1—N1—H1D119.4 (15)O3—C10—C11110.89 (15)
H1C—N1—H1D117 (2)C9—C10—C11110.71 (14)
C11—N2—C12115.42 (13)O3—C10—H10108.8
C11—N2—H2C107.9 (13)C9—C10—H10108.8
C12—N2—H2C107.5 (13)C11—C10—H10108.8
C11—N2—H2D108.2 (12)N2—C11—C10111.63 (13)
C12—N2—H2D109.7 (11)N2—C11—H11A109.3
H2C—N2—H2D107.9 (17)C10—C11—H11A109.3
O1—C1—N1121.91 (19)N2—C11—H11B109.3
O1—C1—C2121.36 (18)C10—C11—H11B109.3
N1—C1—C2116.68 (18)H11A—C11—H11B108.0
C1—C2—C3109.35 (15)C14—C12—C13111.97 (18)
C1—C2—H2A109.8C14—C12—N2108.18 (15)
C3—C2—H2A109.8C13—C12—N2111.17 (14)
C1—C2—H2B109.8C14—C12—H12108.5
C3—C2—H2B109.8C13—C12—H12108.5
H2A—C2—H2B108.3N2—C12—H12108.5
C8—C3—C4118.31 (16)C12—C13—H13A109.5
C8—C3—C2120.98 (17)C12—C13—H13B109.5
C4—C3—C2120.62 (17)H13A—C13—H13B109.5
C5—C4—C3121.07 (18)C12—C13—H13C109.5
C5—C4—H4119.5H13A—C13—H13C109.5
C3—C4—H4119.5H13B—C13—H13C109.5
C6—C5—C4120.11 (17)C12—C14—H14A109.5
C6—C5—H5119.9C12—C14—H14B109.5
C4—C5—H5119.9H14A—C14—H14B109.5
O2—C6—C5115.41 (16)C12—C14—H14C109.5
O2—C6—C7124.68 (17)H14A—C14—H14C109.5
C5—C6—C7119.90 (16)H14B—C14—H14C109.5
C6—C7—C8119.07 (18)C15i—C15—C16115.09 (16)
C6—C7—H7120.5C15i—C15—H15A108.5
C8—C7—H7120.5C16—C15—H15A108.5
C3—C8—C7121.54 (18)C15i—C15—H15B108.5
C3—C8—H8119.2C16—C15—H15B108.5
C7—C8—H8119.2H15A—C15—H15B107.5
O2—C9—C10106.23 (14)O5—C16—O4123.60 (15)
O2—C9—H9A110.5O5—C16—C15118.50 (15)
C10—C9—H9A110.5O4—C16—C15117.89 (14)
O1—C1—C2—C387.6 (2)C4—C3—C8—C70.5 (3)
N1—C1—C2—C390.1 (2)C2—C3—C8—C7176.00 (19)
C1—C2—C3—C882.5 (2)C6—C7—C8—C30.6 (3)
C1—C2—C3—C494.0 (2)C6—O2—C9—C10171.99 (15)
C8—C3—C4—C50.4 (3)O2—C9—C10—O363.35 (18)
C2—C3—C4—C5176.08 (17)O2—C9—C10—C1158.69 (19)
C3—C4—C5—C60.5 (3)C12—N2—C11—C10164.04 (15)
C9—O2—C6—C5151.80 (16)O3—C10—C11—N241.7 (2)
C9—O2—C6—C729.5 (3)C9—C10—C11—N2162.47 (15)
C4—C5—C6—O2178.27 (16)C11—N2—C12—C14174.78 (18)
C4—C5—C6—C70.5 (3)C11—N2—C12—C1361.9 (2)
O2—C6—C7—C8178.09 (18)C15i—C15—C16—O520.4 (3)
C5—C6—C7—C80.6 (3)C15i—C15—C16—O4160.17 (19)
Symmetry code: (i) x+1, y+3, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6A···O10.85 (1)2.06 (1)2.903 (2)171 (3)
O6—H6B···O40.85 (1)2.03 (1)2.880 (2)173 (3)
O3—H3O···O4ii0.87 (1)1.74 (1)2.602 (2)176 (2)
N1—H1C···O1iii0.85 (1)2.17 (1)2.981 (2)159 (2)
N1—H1D···O5iv0.85 (1)2.00 (1)2.824 (2)163 (2)
N2—H2C···O3v0.87 (1)1.99 (1)2.821 (2)162 (2)
N2—H2D···O5ii0.88 (1)1.86 (1)2.743 (2)179 (2)
Symmetry codes: (ii) x+2, y+2, z+1; (iii) x+1, y1/2, z+3/2; (iv) x, y+5/2, z+1/2; (v) x+2, y+1, z+1.
 

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