Bis[(4-acetamido­phen­oxy-2-hydroxy­prop­yl)isopropyl­ammonium] succinate dihydrate

Atenolol, 4-(3-isopropyl­amino­methyl-2-hydroxy­prop­oxy)­phenyl­acetamide, crystallizes as a hydrated succinate salt, 2C₁₄H₂₃N₂O₃⁺·C₄H₄O₄^2-·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.

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

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

Crystal data

2C14H23N2O3^+·C4H4O4^2^−·2H2O	F(000) = 740
Mr = 686.79	Dx = 1.263 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 780 reflections
a = 11.677 (2) Å	θ = 2.8–27.6°
b = 9.377 (1) Å	µ = 0.10 mm^−1
c = 17.225 (2) Å	T = 295 K
β = 106.682 (3)°	Block, colorless
V = 1806.6 (4) Å^3	0.50 × 0.20 × 0.16 mm
Z = 2

Data collection

Bruker SMART 1K area-detector diffractometer	2498 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
Graphite monochromator	θmax = 27.5°, θmin = 2.5°
φ and ω scans	h = −15→12
11319 measured reflections	k = −12→11
4126 independent reflections	l = −22→22

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0582P)^2 + 0.1974P] where P = (Fo^2 + 2Fc^2)/3
4126 reflections	(Δ/σ)max < 0.001
245 parameters	Δρmax = 0.22 e Å^−3
7 restraints	Δρmin = −0.14 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.58609 (15)	1.21190 (15)	0.73748 (10)	0.0717 (5)
O2	0.89722 (11)	0.76264 (14)	0.57228 (8)	0.0542 (4)
O3	1.06272 (10)	0.66009 (14)	0.49992 (7)	0.0426 (3)
H3O	1.1249 (13)	0.637 (2)	0.4846 (12)	0.065 (6)*
O4	0.75356 (11)	1.39729 (13)	0.55153 (7)	0.0456 (3)
O5	0.65756 (11)	1.47625 (17)	0.43012 (7)	0.0607 (4)
O6	0.78218 (17)	1.3904 (2)	0.72321 (11)	0.0821 (5)
H6a	0.731 (2)	1.331 (2)	0.7286 (18)	0.111 (12)*
H6B	0.774 (3)	1.400 (3)	0.6725 (7)	0.105 (10)*
N1	0.51664 (16)	1.00386 (19)	0.76707 (10)	0.0491 (4)
H1c	0.4809 (18)	0.9254 (15)	0.7524 (13)	0.066 (7)*
H1D	0.5464 (18)	1.018 (2)	0.8178 (6)	0.067 (7)*
N2	1.14239 (13)	0.45027 (17)	0.61397 (9)	0.0391 (4)
H2C	1.0896 (14)	0.4157 (19)	0.5721 (8)	0.051 (6)*
H2D	1.2063 (11)	0.4729 (18)	0.5990 (10)	0.041 (5)*
C1	0.53720 (17)	1.0965 (2)	0.71532 (11)	0.0437 (4)
C2	0.50215 (18)	1.0524 (2)	0.62752 (11)	0.0531 (5)
H2A	0.4796	1.1358	0.5932	0.064*
H2B	0.4340	0.9886	0.6164	0.064*
C3	0.60692 (16)	0.97788 (19)	0.60926 (10)	0.0416 (4)
C4	0.61705 (17)	0.8316 (2)	0.61357 (11)	0.0468 (5)
H4	0.5566	0.7779	0.6245	0.056*
C5	0.71535 (16)	0.7635 (2)	0.60188 (12)	0.0483 (5)
H5	0.7210	0.6646	0.6054	0.058*
C6	0.80487 (16)	0.84124 (19)	0.58509 (11)	0.0414 (4)
C7	0.79685 (19)	0.9879 (2)	0.58056 (13)	0.0547 (5)
H7	0.8575	1.0415	0.5697	0.066*
C8	0.69688 (19)	1.0544 (2)	0.59247 (12)	0.0550 (5)
H8	0.6909	1.1533	0.5889	0.066*
C9	1.01344 (15)	0.8242 (2)	0.59055 (11)	0.0444 (4)
H9A	1.0372	0.8615	0.6454	0.053*
H9B	1.0146	0.9014	0.5533	0.053*
C10	1.09645 (15)	0.7061 (2)	0.58174 (10)	0.0419 (4)
H10	1.1782	0.7435	0.5955	0.050*
C11	1.09255 (18)	0.5833 (2)	0.63835 (11)	0.0479 (5)
H11A	1.1380	0.6086	0.6931	0.058*
H11B	1.0104	0.5668	0.6381	0.058*
C12	1.17350 (16)	0.3349 (2)	0.67751 (11)	0.0454 (5)
H12	1.2308	0.3738	0.7261	0.055*
C13	1.06418 (18)	0.2854 (3)	0.69984 (13)	0.0620 (6)
H13A	1.0867	0.2134	0.7411	0.093*
H13B	1.0073	0.2465	0.6528	0.093*
H13C	1.0290	0.3646	0.7199	0.093*
C14	1.2327 (2)	0.2152 (3)	0.64573 (16)	0.0761 (7)
H14A	1.2538	0.1408	0.6856	0.114*
H14B	1.3035	0.2500	0.6344	0.114*
H14C	1.1786	0.1783	0.5969	0.114*
C15	0.54743 (14)	1.45125 (18)	0.52570 (10)	0.0370 (4)
H15A	0.5139	1.3563	0.5242	0.044*
H15B	0.5678	1.4842	0.5814	0.044*
C16	0.66113 (15)	1.44139 (17)	0.50039 (10)	0.0338 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0906 (12)	0.0457 (8)	0.0963 (12)	−0.0088 (8)	0.0548 (10)	−0.0083 (8)
O2	0.0338 (7)	0.0494 (8)	0.0813 (10)	0.0034 (6)	0.0195 (7)	−0.0200 (7)
O3	0.0288 (7)	0.0648 (8)	0.0364 (7)	0.0074 (6)	0.0127 (5)	−0.0031 (6)
O4	0.0317 (7)	0.0642 (8)	0.0436 (7)	0.0123 (6)	0.0151 (6)	0.0088 (6)
O5	0.0335 (7)	0.1165 (12)	0.0370 (7)	0.0126 (8)	0.0180 (6)	0.0169 (7)
O6	0.0634 (11)	0.1238 (16)	0.0567 (11)	−0.0125 (11)	0.0135 (9)	−0.0046 (11)
N1	0.0545 (11)	0.0511 (10)	0.0434 (10)	−0.0065 (9)	0.0166 (9)	−0.0018 (8)
N2	0.0263 (8)	0.0577 (9)	0.0352 (8)	0.0086 (7)	0.0120 (7)	0.0041 (7)
C1	0.0404 (10)	0.0433 (10)	0.0547 (11)	0.0120 (9)	0.0251 (9)	0.0025 (9)
C2	0.0479 (12)	0.0686 (13)	0.0461 (11)	0.0241 (10)	0.0186 (9)	0.0093 (10)
C3	0.0396 (10)	0.0521 (11)	0.0339 (9)	0.0139 (9)	0.0115 (8)	0.0024 (8)
C4	0.0395 (11)	0.0496 (11)	0.0534 (12)	−0.0014 (9)	0.0164 (9)	−0.0095 (9)
C5	0.0433 (11)	0.0384 (10)	0.0627 (12)	0.0009 (9)	0.0146 (9)	−0.0102 (9)
C6	0.0360 (10)	0.0440 (10)	0.0438 (10)	0.0081 (8)	0.0107 (8)	−0.0095 (8)
C7	0.0543 (13)	0.0474 (11)	0.0747 (14)	0.0006 (10)	0.0385 (11)	0.0021 (10)
C8	0.0670 (14)	0.0406 (10)	0.0690 (14)	0.0148 (10)	0.0382 (12)	0.0078 (9)
C9	0.0362 (10)	0.0491 (11)	0.0500 (11)	−0.0032 (8)	0.0161 (8)	−0.0085 (9)
C10	0.0304 (9)	0.0570 (11)	0.0391 (10)	0.0029 (8)	0.0113 (8)	−0.0041 (8)
C11	0.0471 (11)	0.0607 (12)	0.0405 (10)	0.0123 (9)	0.0199 (9)	−0.0009 (9)
C12	0.0333 (10)	0.0622 (12)	0.0384 (10)	0.0077 (9)	0.0065 (8)	0.0126 (9)
C13	0.0510 (13)	0.0859 (16)	0.0515 (12)	−0.0017 (12)	0.0184 (10)	0.0184 (11)
C14	0.0791 (17)	0.0716 (15)	0.0856 (17)	0.0329 (14)	0.0366 (14)	0.0300 (13)
C15	0.0272 (9)	0.0487 (10)	0.0392 (9)	0.0009 (8)	0.0164 (7)	0.0049 (8)
C16	0.0291 (9)	0.0394 (9)	0.0353 (9)	0.0005 (7)	0.0130 (7)	−0.0006 (7)

Geometric parameters (Å, º)

O1—C1	1.232 (2)	C5—H5	0.9300
O2—C6	1.375 (2)	C6—C7	1.379 (3)
O2—C9	1.424 (2)	C7—C8	1.390 (3)
O3—C10	1.418 (2)	C7—H7	0.9300
O3—H3O	0.867 (9)	C8—H8	0.9300
O4—C16	1.251 (2)	C9—C10	1.508 (2)
O5—C16	1.2430 (19)	C9—H9A	0.9700
O6—H6a	0.847 (10)	C9—H9B	0.9700
O6—H6B	0.854 (10)	C10—C11	1.518 (3)
N1—C1	1.315 (2)	C10—H10	0.9800
N1—H1c	0.853 (9)	C11—H11A	0.9700
N1—H1D	0.848 (10)	C11—H11B	0.9700
N2—C11	1.487 (2)	C12—C14	1.501 (3)
N2—C12	1.507 (2)	C12—C13	1.509 (2)
N2—H2C	0.866 (9)	C12—H12	0.9800
N2—H2D	0.883 (9)	C13—H13A	0.9600
C1—C2	1.507 (3)	C13—H13B	0.9600
C2—C3	1.518 (2)	C13—H13C	0.9600
C2—H2A	0.9700	C14—H14A	0.9600
C2—H2B	0.9700	C14—H14B	0.9600
C3—C8	1.370 (3)	C14—H14C	0.9600
C3—C4	1.377 (3)	C15—C15^i	1.511 (3)
C4—C5	1.378 (2)	C15—C16	1.514 (2)
C4—H4	0.9300	C15—H15A	0.9700
C5—C6	1.372 (2)	C15—H15B	0.9700
C6—O2—C9	119.25 (14)	O2—C9—H9B	110.5
C10—O3—H3O	111.1 (14)	C10—C9—H9B	110.5
H6a—O6—H6b	108 (3)	H9A—C9—H9B	108.7
C1—N1—H1C	122.8 (15)	O3—C10—C9	108.70 (14)
C1—N1—H1D	119.4 (15)	O3—C10—C11	110.89 (15)
H1C—N1—H1D	117 (2)	C9—C10—C11	110.71 (14)
C11—N2—C12	115.42 (13)	O3—C10—H10	108.8
C11—N2—H2C	107.9 (13)	C9—C10—H10	108.8
C12—N2—H2C	107.5 (13)	C11—C10—H10	108.8
C11—N2—H2D	108.2 (12)	N2—C11—C10	111.63 (13)
C12—N2—H2D	109.7 (11)	N2—C11—H11A	109.3
H2C—N2—H2D	107.9 (17)	C10—C11—H11A	109.3
O1—C1—N1	121.91 (19)	N2—C11—H11B	109.3
O1—C1—C2	121.36 (18)	C10—C11—H11B	109.3
N1—C1—C2	116.68 (18)	H11A—C11—H11B	108.0
C1—C2—C3	109.35 (15)	C14—C12—C13	111.97 (18)
C1—C2—H2A	109.8	C14—C12—N2	108.18 (15)
C3—C2—H2A	109.8	C13—C12—N2	111.17 (14)
C1—C2—H2B	109.8	C14—C12—H12	108.5
C3—C2—H2B	109.8	C13—C12—H12	108.5
H2A—C2—H2B	108.3	N2—C12—H12	108.5
C8—C3—C4	118.31 (16)	C12—C13—H13A	109.5
C8—C3—C2	120.98 (17)	C12—C13—H13B	109.5
C4—C3—C2	120.62 (17)	H13A—C13—H13B	109.5
C5—C4—C3	121.07 (18)	C12—C13—H13C	109.5
C5—C4—H4	119.5	H13A—C13—H13C	109.5
C3—C4—H4	119.5	H13B—C13—H13C	109.5
C6—C5—C4	120.11 (17)	C12—C14—H14A	109.5
C6—C5—H5	119.9	C12—C14—H14B	109.5
C4—C5—H5	119.9	H14A—C14—H14B	109.5
O2—C6—C5	115.41 (16)	C12—C14—H14C	109.5
O2—C6—C7	124.68 (17)	H14A—C14—H14C	109.5
C5—C6—C7	119.90 (16)	H14B—C14—H14C	109.5
C6—C7—C8	119.07 (18)	C15^i—C15—C16	115.09 (16)
C6—C7—H7	120.5	C15^i—C15—H15A	108.5
C8—C7—H7	120.5	C16—C15—H15A	108.5
C3—C8—C7	121.54 (18)	C15^i—C15—H15B	108.5
C3—C8—H8	119.2	C16—C15—H15B	108.5
C7—C8—H8	119.2	H15A—C15—H15B	107.5
O2—C9—C10	106.23 (14)	O5—C16—O4	123.60 (15)
O2—C9—H9A	110.5	O5—C16—C15	118.50 (15)
C10—C9—H9A	110.5	O4—C16—C15	117.89 (14)
O1—C1—C2—C3	87.6 (2)	C4—C3—C8—C7	−0.5 (3)
N1—C1—C2—C3	−90.1 (2)	C2—C3—C8—C7	176.00 (19)
C1—C2—C3—C8	−82.5 (2)	C6—C7—C8—C3	0.6 (3)
C1—C2—C3—C4	94.0 (2)	C6—O2—C9—C10	171.99 (15)
C8—C3—C4—C5	0.4 (3)	O2—C9—C10—O3	63.35 (18)
C2—C3—C4—C5	−176.08 (17)	O2—C9—C10—C11	−58.69 (19)
C3—C4—C5—C6	−0.5 (3)	C12—N2—C11—C10	164.04 (15)
C9—O2—C6—C5	−151.80 (16)	O3—C10—C11—N2	41.7 (2)
C9—O2—C6—C7	29.5 (3)	C9—C10—C11—N2	162.47 (15)
C4—C5—C6—O2	−178.27 (16)	C11—N2—C12—C14	−174.78 (18)
C4—C5—C6—C7	0.5 (3)	C11—N2—C12—C13	61.9 (2)
O2—C6—C7—C8	178.09 (18)	C15^i—C15—C16—O5	−20.4 (3)
C5—C6—C7—C8	−0.6 (3)	C15^i—C15—C16—O4	160.17 (19)

Symmetry code: (i) −x+1, −y+3, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O1	0.85 (1)	2.06 (1)	2.903 (2)	171 (3)
O6—H6B···O4	0.85 (1)	2.03 (1)	2.880 (2)	173 (3)
O3—H3O···O4^ii	0.87 (1)	1.74 (1)	2.602 (2)	176 (2)
N1—H1C···O1^iii	0.85 (1)	2.17 (1)	2.981 (2)	159 (2)
N1—H1D···O5^iv	0.85 (1)	2.00 (1)	2.824 (2)	163 (2)
N2—H2C···O3^v	0.87 (1)	1.99 (1)	2.821 (2)	162 (2)
N2—H2D···O5^ii	0.88 (1)	1.86 (1)	2.743 (2)	179 (2)

Symmetry codes: (ii) −x+2, −y+2, −z+1; (iii) −x+1, y−1/2, −z+3/2; (iv) x, −y+5/2, z+1/2; (v) −x+2, −y+1, −z+1.