Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807049331/hb2574sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807049331/hb2574Isup2.hkl |
CCDC reference: 667346
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.058
- wR factor = 0.151
- Data-to-parameter ratio = 7.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.62 PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.19 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C19 - C20 .. 5.56 su PLAT230_ALERT_2_C Hirshfeld Test Diff for O3 - C2 .. 6.61 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C15 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C23 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C22 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C25 PLAT245_ALERT_2_C U(iso) H2A Smaller than U(eq) N2 by ... 0.01 AngSq PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5 PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1A ... ? PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1B ... ?
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.99 From the CIF: _reflns_number_total 2385 Count of symmetry unique reflns 2423 Completeness (_total/calc) 98.43% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 67
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 13 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 9 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
A 5-ml ethanol solution of 4,4'-methylene bis(benzenamine) (1.0 mmol, 0.20 g) added to a 20-ml hot aqueous solution of benzylic acid (1.0 mmol, 0.23 g) and the mixture was stirred for 15 minutes under the temperature of 373 K. Then the solution was filtered, and the filtrate was kept at the room temperature. After a week, colorless blades of (I) were obtained.
Anomalous dispersion was negligible and Friedel pairs were merged before refinement. H atoms bonded to nitrogen atoms and hydroxyl group were located in a difference synthesis and refined isotropically with N—H = 0.90 (1) Å and O—H = 0.82 (1) Å, respectively. All the remaining H atoms were placed in calculated positions, with C—H = 0.93 and 0.97 Å for aromatic and methylene H atoms, respectively, and were refined as riding with Uiso = 1.2Ueq(C).
This work continues our previous synthetic and structural studies of hydrogen bonding interactions between the 2-hydroxy-2,2-diphenylacetate anion and substituted pyridinium cations (Li, 2007).
The asymmetric unit of the title compound, (I), contains one 4,4'-methylene bis(benzenammonium) cation and one 2-hydroxy-2,2-diphenylacetate anion, in which these component ions are linked together through an N—H···O hydrogen bond (Table 1, Fig. 1). The dihedral angles between the aromatic ring planes in the cation and the anion are 83.87 (18)° and 75.48 (17)°, respectively. An intramolecular O–H···O hydrogen bond occurs within the benzylate anion and a S(5) ring (Bernstein et al., 1995) is generated. Moreover, adjacent ion pairs are further extended into an infinite one-dimensional chain along [010] by further intermolecular N—H···O hydrogen bonds (Fig. 2).
For related literature, see: Li (2007); Bernstein et al. (1995).
Data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).
C13H15N2+·C14H11O3− | F(000) = 452 |
Mr = 426.50 | Dx = 1.250 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 2500 reflections |
a = 13.336 (6) Å | θ = 2.3–28.2° |
b = 6.477 (3) Å | µ = 0.08 mm−1 |
c = 14.454 (7) Å | T = 298 K |
β = 114.777 (7)° | Blade, colourless |
V = 1133.6 (9) Å3 | 0.35 × 0.12 × 0.09 mm |
Z = 2 |
Bruker SMART APEX CCD diffractometer | 2385 independent reflections |
Radiation source: fine-focus sealed tube | 1701 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
ω scans | θmax = 26.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −16→14 |
Tmin = 0.972, Tmax = 0.993 | k = −7→6 |
5069 measured reflections | l = −12→17 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.151 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0779P)2 + 0.0728P] where P = (Fo2 + 2Fc2)/3 |
2385 reflections | (Δ/σ)max = 0.005 |
313 parameters | Δρmax = 0.37 e Å−3 |
67 restraints | Δρmin = −0.34 e Å−3 |
C13H15N2+·C14H11O3− | V = 1133.6 (9) Å3 |
Mr = 426.50 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 13.336 (6) Å | µ = 0.08 mm−1 |
b = 6.477 (3) Å | T = 298 K |
c = 14.454 (7) Å | 0.35 × 0.12 × 0.09 mm |
β = 114.777 (7)° |
Bruker SMART APEX CCD diffractometer | 2385 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | 1701 reflections with I > 2σ(I) |
Tmin = 0.972, Tmax = 0.993 | Rint = 0.034 |
5069 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 67 restraints |
wR(F2) = 0.151 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.37 e Å−3 |
2385 reflections | Δρmin = −0.34 e Å−3 |
313 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.7443 (3) | −0.0297 (6) | 0.4427 (2) | 0.0852 (4) | |
H1A | 0.7667 (13) | −0.121 (3) | 0.4114 (13) | 0.0836 (5)* | |
H1B | 0.7345 (14) | 0.038 (3) | 0.4904 (11) | 0.0836 (5)* | |
N2 | 0.08804 (18) | 0.6545 (3) | 0.07426 (16) | 0.0424 (7) | |
H2A | 0.0770 (14) | 0.7807 (16) | 0.0951 (14) | 0.031 (7)* | |
H2B | 0.0346 (14) | 0.636 (5) | 0.0108 (9) | 0.067 (10)* | |
H2C | 0.0708 (13) | 0.558 (2) | 0.1107 (13) | 0.073 (11)* | |
O1 | 0.05811 (15) | 1.0586 (3) | 0.11769 (13) | 0.0446 (5) | |
O2 | 0.03234 (17) | 1.3555 (3) | 0.18013 (16) | 0.0609 (6) | |
O3 | 0.09565 (15) | 1.2283 (3) | 0.36568 (14) | 0.0504 (4) | |
H3 | 0.0516 (14) | 1.306 (2) | 0.3220 (13) | 0.0494 (5)* | |
C1 | 0.0580 (2) | 1.1684 (4) | 0.1886 (2) | 0.0372 (7) | |
C2 | 0.0943 (2) | 1.0716 (5) | 0.2953 (2) | 0.0456 (5) | |
C3 | 0.0175 (2) | 0.8989 (5) | 0.2980 (2) | 0.0427 (8) | |
C4 | −0.0720 (2) | 0.8274 (5) | 0.2139 (3) | 0.0551 (10) | |
H4 | −0.0888 | 0.8849 | 0.1501 | 0.066* | |
C5 | −0.1370 (3) | 0.6698 (6) | 0.2241 (3) | 0.0744 (12) | |
H5 | −0.1967 | 0.6208 | 0.1671 | 0.089* | |
C6 | −0.1138 (3) | 0.5862 (7) | 0.3177 (3) | 0.0817 (12) | |
H6 | −0.1577 | 0.4807 | 0.3241 | 0.098* | |
C7 | −0.0272 (3) | 0.6567 (6) | 0.4007 (3) | 0.0767 (11) | |
H7 | −0.0116 | 0.5995 | 0.4643 | 0.092* | |
C8 | 0.0380 (2) | 0.8128 (5) | 0.3916 (2) | 0.0557 (9) | |
H8 | 0.0969 | 0.8612 | 0.4496 | 0.067* | |
C9 | 0.2128 (2) | 0.9993 (5) | 0.32753 (19) | 0.0387 (8) | |
C10 | 0.2426 (2) | 0.7957 (5) | 0.3236 (2) | 0.0432 (8) | |
H10 | 0.1885 | 0.6938 | 0.3033 | 0.052* | |
C11 | 0.3508 (2) | 0.7417 (6) | 0.3492 (2) | 0.0549 (9) | |
H11 | 0.3694 | 0.6039 | 0.3473 | 0.066* | |
C12 | 0.4309 (3) | 0.8897 (6) | 0.3772 (2) | 0.0637 (11) | |
H12 | 0.5037 | 0.8538 | 0.3926 | 0.076* | |
C13 | 0.4033 (3) | 1.0900 (6) | 0.3823 (3) | 0.0747 (12) | |
H13 | 0.4579 | 1.1911 | 0.4022 | 0.090* | |
C14 | 0.2957 (3) | 1.1449 (6) | 0.3584 (3) | 0.0666 (11) | |
H14 | 0.2786 | 1.2826 | 0.3632 | 0.080* | |
C15 | 0.5325 (3) | 0.5414 (7) | 0.1174 (3) | 0.0720 (12) | |
H15A | 0.5331 | 0.4874 | 0.0550 | 0.086* | |
H15B | 0.5704 | 0.6733 | 0.1315 | 0.086* | |
C16 | 0.5942 (2) | 0.3939 (6) | 0.2040 (2) | 0.0518 (9) | |
C17 | 0.6351 (3) | 0.2125 (6) | 0.1885 (2) | 0.0648 (11) | |
H17 | 0.6273 | 0.1796 | 0.1232 | 0.078* | |
C18 | 0.6881 (3) | 0.0748 (6) | 0.2670 (3) | 0.0748 (12) | |
H18 | 0.7166 | −0.0474 | 0.2542 | 0.090* | |
C19 | 0.6987 (3) | 0.1173 (7) | 0.3634 (3) | 0.0815 (6) | |
C20 | 0.6607 (2) | 0.3063 (7) | 0.3806 (2) | 0.0693 (12) | |
H20 | 0.6708 | 0.3423 | 0.4462 | 0.083* | |
C21 | 0.6089 (3) | 0.4393 (6) | 0.3022 (3) | 0.0613 (11) | |
H21 | 0.5826 | 0.5640 | 0.3151 | 0.074* | |
C22 | 0.4140 (2) | 0.5740 (6) | 0.1020 (2) | 0.0548 (9) | |
C23 | 0.3468 (3) | 0.4093 (6) | 0.0959 (3) | 0.0828 (14) | |
H23 | 0.3743 | 0.2764 | 0.0984 | 0.099* | |
C24 | 0.2398 (3) | 0.4332 (5) | 0.0861 (3) | 0.0735 (14) | |
H24 | 0.1962 | 0.3188 | 0.0824 | 0.088* | |
C25 | 0.1999 (2) | 0.6279 (4) | 0.0821 (2) | 0.0410 (8) | |
C26 | 0.2638 (3) | 0.7928 (5) | 0.0868 (3) | 0.0631 (10) | |
H26 | 0.2359 | 0.9256 | 0.0834 | 0.076* | |
C27 | 0.3705 (3) | 0.7642 (6) | 0.0967 (3) | 0.0634 (10) | |
H27 | 0.4136 | 0.8792 | 0.0998 | 0.076* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0838 (5) | 0.0846 (5) | 0.0840 (5) | −0.0006 (5) | 0.0320 (5) | 0.0028 (5) |
N2 | 0.0431 (12) | 0.0351 (12) | 0.0406 (12) | 0.0053 (11) | 0.0092 (10) | 0.0012 (11) |
O1 | 0.0542 (10) | 0.0411 (11) | 0.0327 (9) | 0.0047 (10) | 0.0125 (8) | −0.0027 (9) |
O2 | 0.0853 (13) | 0.0403 (12) | 0.0712 (11) | 0.0183 (11) | 0.0466 (10) | 0.0154 (10) |
O3 | 0.0534 (5) | 0.0472 (5) | 0.0485 (5) | 0.0033 (5) | 0.0192 (5) | −0.0058 (5) |
C1 | 0.0332 (13) | 0.0301 (14) | 0.0467 (14) | 0.0003 (12) | 0.0152 (11) | 0.0005 (12) |
C2 | 0.0499 (7) | 0.0436 (8) | 0.0448 (7) | 0.0030 (7) | 0.0211 (7) | −0.0065 (7) |
C3 | 0.0392 (13) | 0.0397 (16) | 0.0556 (15) | 0.0073 (12) | 0.0261 (11) | −0.0027 (13) |
C4 | 0.0417 (15) | 0.055 (2) | 0.0672 (18) | −0.0041 (15) | 0.0218 (14) | −0.0059 (16) |
C5 | 0.0455 (16) | 0.075 (3) | 0.105 (3) | −0.0162 (19) | 0.0339 (17) | −0.013 (2) |
C6 | 0.0689 (18) | 0.065 (2) | 0.133 (3) | 0.0030 (19) | 0.0631 (17) | 0.013 (2) |
C7 | 0.0730 (18) | 0.078 (2) | 0.101 (2) | 0.017 (2) | 0.0582 (16) | 0.037 (2) |
C8 | 0.0512 (15) | 0.060 (2) | 0.0647 (17) | 0.0075 (16) | 0.0331 (13) | 0.0121 (16) |
C9 | 0.0389 (14) | 0.0387 (15) | 0.0324 (13) | −0.0027 (12) | 0.0090 (11) | −0.0054 (12) |
C10 | 0.0408 (14) | 0.0454 (18) | 0.0403 (13) | −0.0015 (14) | 0.0141 (11) | −0.0046 (13) |
C11 | 0.0496 (16) | 0.0562 (19) | 0.0561 (16) | 0.0145 (16) | 0.0195 (13) | 0.0075 (17) |
C12 | 0.0366 (16) | 0.080 (3) | 0.065 (2) | 0.0069 (18) | 0.0122 (15) | −0.0075 (19) |
C13 | 0.0450 (17) | 0.071 (2) | 0.099 (3) | −0.0225 (18) | 0.0217 (17) | −0.021 (2) |
C14 | 0.0548 (18) | 0.050 (2) | 0.090 (2) | −0.0086 (17) | 0.0255 (17) | −0.0165 (18) |
C15 | 0.0590 (18) | 0.078 (2) | 0.079 (2) | 0.0088 (19) | 0.0286 (16) | 0.026 (2) |
C16 | 0.0382 (14) | 0.069 (2) | 0.0492 (16) | 0.0012 (16) | 0.0192 (12) | 0.0042 (16) |
C17 | 0.0620 (18) | 0.080 (3) | 0.0461 (16) | 0.0125 (19) | 0.0168 (15) | −0.0044 (18) |
C18 | 0.069 (2) | 0.064 (2) | 0.083 (2) | 0.0182 (19) | 0.0236 (18) | −0.003 (2) |
C19 | 0.0796 (8) | 0.0830 (8) | 0.0803 (8) | −0.0017 (8) | 0.0320 (8) | 0.0049 (8) |
C20 | 0.0512 (18) | 0.109 (3) | 0.0409 (15) | −0.006 (2) | 0.0120 (14) | −0.0057 (18) |
C21 | 0.0473 (16) | 0.073 (2) | 0.0655 (19) | −0.0008 (17) | 0.0260 (14) | −0.0143 (18) |
C22 | 0.0481 (15) | 0.056 (2) | 0.0562 (17) | 0.0061 (16) | 0.0179 (13) | 0.0106 (17) |
C23 | 0.058 (2) | 0.050 (2) | 0.128 (3) | 0.0112 (18) | 0.026 (2) | 0.008 (2) |
C24 | 0.0470 (18) | 0.0326 (17) | 0.128 (3) | 0.0000 (15) | 0.024 (2) | 0.000 (2) |
C25 | 0.0429 (14) | 0.0386 (16) | 0.0339 (13) | 0.0050 (13) | 0.0087 (12) | 0.0013 (12) |
C26 | 0.0788 (19) | 0.0389 (18) | 0.088 (2) | 0.0061 (17) | 0.0508 (16) | 0.0031 (16) |
C27 | 0.0634 (17) | 0.0506 (19) | 0.093 (2) | −0.0058 (17) | 0.0494 (15) | 0.0045 (18) |
N1—C19 | 1.416 (5) | C11—H11 | 0.9300 |
N1—H1A | 0.872 (10) | C12—C13 | 1.359 (6) |
N1—H1B | 0.870 (10) | C12—H12 | 0.9300 |
N2—C25 | 1.458 (4) | C13—C14 | 1.375 (5) |
N2—H2A | 0.904 (9) | C13—H13 | 0.9300 |
N2—H2B | 0.903 (9) | C14—H14 | 0.9300 |
N2—H2C | 0.905 (10) | C15—C16 | 1.514 (5) |
O1—C1 | 1.249 (3) | C15—C22 | 1.515 (5) |
O2—C1 | 1.251 (3) | C15—H15A | 0.9700 |
O3—C2 | 1.432 (4) | C15—H15B | 0.9700 |
O3—H3 | 0.827 (9) | C16—C17 | 1.353 (5) |
C1—C2 | 1.542 (4) | C16—C21 | 1.381 (5) |
C2—C9 | 1.522 (4) | C17—C18 | 1.382 (5) |
C2—C3 | 1.528 (4) | C17—H17 | 0.9300 |
C3—C8 | 1.381 (4) | C18—C19 | 1.368 (6) |
C3—C4 | 1.379 (4) | C18—H18 | 0.9300 |
C4—C5 | 1.387 (5) | C19—C20 | 1.386 (6) |
C4—H4 | 0.9300 | C20—C21 | 1.359 (5) |
C5—C6 | 1.366 (6) | C20—H20 | 0.9300 |
C5—H5 | 0.9300 | C21—H21 | 0.9300 |
C6—C7 | 1.349 (5) | C22—C27 | 1.350 (5) |
C6—H6 | 0.9300 | C22—C23 | 1.372 (5) |
C7—C8 | 1.375 (5) | C23—C24 | 1.382 (5) |
C7—H7 | 0.9300 | C23—H23 | 0.9300 |
C8—H8 | 0.9300 | C24—C25 | 1.361 (4) |
C9—C14 | 1.378 (4) | C24—H24 | 0.9300 |
C9—C10 | 1.385 (4) | C25—C26 | 1.350 (4) |
C10—C11 | 1.376 (4) | C26—C27 | 1.382 (5) |
C10—H10 | 0.9300 | C26—H26 | 0.9300 |
C11—C12 | 1.364 (5) | C27—H27 | 0.9300 |
C19—N1—H1A | 99.2 (14) | C12—C13—C14 | 120.7 (3) |
C19—N1—H1B | 98.5 (15) | C12—C13—H13 | 119.6 |
H1A—N1—H1B | 161.9 (19) | C14—C13—H13 | 119.6 |
C25—N2—H2A | 112.6 (12) | C9—C14—C13 | 121.0 (3) |
C25—N2—H2B | 114.1 (15) | C9—C14—H14 | 119.5 |
H2A—N2—H2B | 107 (2) | C13—C14—H14 | 119.5 |
C25—N2—H2C | 112.0 (12) | C16—C15—C22 | 112.4 (3) |
H2A—N2—H2C | 108.2 (18) | C16—C15—H15A | 109.1 |
H2B—N2—H2C | 102 (2) | C22—C15—H15A | 109.1 |
C2—O3—H3 | 95.4 (14) | C16—C15—H15B | 109.1 |
O2—C1—O1 | 124.4 (3) | C22—C15—H15B | 109.1 |
O2—C1—C2 | 116.8 (3) | H15A—C15—H15B | 107.9 |
O1—C1—C2 | 118.8 (2) | C17—C16—C21 | 117.4 (3) |
O3—C2—C9 | 107.4 (2) | C17—C16—C15 | 121.9 (3) |
O3—C2—C3 | 108.0 (2) | C21—C16—C15 | 120.6 (3) |
C9—C2—C3 | 112.8 (2) | C16—C17—C18 | 121.9 (3) |
O3—C2—C1 | 109.1 (2) | C16—C17—H17 | 119.0 |
C9—C2—C1 | 106.4 (2) | C18—C17—H17 | 119.0 |
C3—C2—C1 | 113.0 (2) | C19—C18—C17 | 120.3 (4) |
C8—C3—C4 | 118.1 (3) | C19—C18—H18 | 119.8 |
C8—C3—C2 | 117.4 (2) | C17—C18—H18 | 119.8 |
C4—C3—C2 | 124.4 (3) | C18—C19—C20 | 118.0 (4) |
C3—C4—C5 | 120.1 (3) | C18—C19—N1 | 121.0 (4) |
C3—C4—H4 | 119.9 | C20—C19—N1 | 120.9 (4) |
C5—C4—H4 | 119.9 | C21—C20—C19 | 120.5 (3) |
C6—C5—C4 | 120.3 (3) | C21—C20—H20 | 119.8 |
C6—C5—H5 | 119.8 | C19—C20—H20 | 119.8 |
C4—C5—H5 | 119.8 | C20—C21—C16 | 121.7 (4) |
C7—C6—C5 | 120.0 (4) | C20—C21—H21 | 119.1 |
C7—C6—H6 | 120.0 | C16—C21—H21 | 119.1 |
C5—C6—H6 | 120.0 | C27—C22—C23 | 116.9 (3) |
C6—C7—C8 | 120.3 (4) | C27—C22—C15 | 122.2 (3) |
C6—C7—H7 | 119.9 | C23—C22—C15 | 120.9 (3) |
C8—C7—H7 | 119.9 | C22—C23—C24 | 122.5 (3) |
C7—C8—C3 | 121.1 (3) | C22—C23—H23 | 118.7 |
C7—C8—H8 | 119.5 | C24—C23—H23 | 118.7 |
C3—C8—H8 | 119.5 | C25—C24—C23 | 118.5 (3) |
C14—C9—C10 | 117.4 (3) | C25—C24—H24 | 120.7 |
C14—C9—C2 | 118.5 (3) | C23—C24—H24 | 120.7 |
C10—C9—C2 | 124.0 (3) | C26—C25—C24 | 120.2 (3) |
C11—C10—C9 | 121.2 (3) | C26—C25—N2 | 120.9 (3) |
C11—C10—H10 | 119.4 | C24—C25—N2 | 118.9 (3) |
C9—C10—H10 | 119.4 | C25—C26—C27 | 120.0 (3) |
C12—C11—C10 | 120.2 (3) | C25—C26—H26 | 120.0 |
C12—C11—H11 | 119.9 | C27—C26—H26 | 120.0 |
C10—C11—H11 | 119.9 | C22—C27—C26 | 121.8 (3) |
C11—C12—C13 | 119.4 (3) | C22—C27—H27 | 119.1 |
C11—C12—H12 | 120.3 | C26—C27—H27 | 119.1 |
C13—C12—H12 | 120.3 |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2 | 0.83 (1) | 1.98 (2) | 2.586 (3) | 129 (2) |
N2—H2C···O2i | 0.91 (1) | 1.85 (1) | 2.756 (3) | 178 (2) |
N2—H2B···O1ii | 0.90 (1) | 1.82 (1) | 2.711 (3) | 170 (3) |
N2—H2A···O1 | 0.90 (1) | 1.87 (1) | 2.759 (3) | 170 (2) |
Symmetry codes: (i) x, y−1, z; (ii) −x, y−1/2, −z. |
Experimental details
Crystal data | |
Chemical formula | C13H15N2+·C14H11O3− |
Mr | 426.50 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 298 |
a, b, c (Å) | 13.336 (6), 6.477 (3), 14.454 (7) |
β (°) | 114.777 (7) |
V (Å3) | 1133.6 (9) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.35 × 0.12 × 0.09 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2001) |
Tmin, Tmax | 0.972, 0.993 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5069, 2385, 1701 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.151, 1.06 |
No. of reflections | 2385 |
No. of parameters | 313 |
No. of restraints | 67 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.37, −0.34 |
Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2 | 0.827 (9) | 1.984 (19) | 2.586 (3) | 129 (2) |
N2—H2C···O2i | 0.905 (10) | 1.851 (11) | 2.756 (3) | 177.5 (18) |
N2—H2B···O1ii | 0.903 (9) | 1.818 (11) | 2.711 (3) | 170 (3) |
N2—H2A···O1 | 0.904 (9) | 1.865 (9) | 2.759 (3) | 169.6 (19) |
Symmetry codes: (i) x, y−1, z; (ii) −x, y−1/2, −z. |
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This work continues our previous synthetic and structural studies of hydrogen bonding interactions between the 2-hydroxy-2,2-diphenylacetate anion and substituted pyridinium cations (Li, 2007).
The asymmetric unit of the title compound, (I), contains one 4,4'-methylene bis(benzenammonium) cation and one 2-hydroxy-2,2-diphenylacetate anion, in which these component ions are linked together through an N—H···O hydrogen bond (Table 1, Fig. 1). The dihedral angles between the aromatic ring planes in the cation and the anion are 83.87 (18)° and 75.48 (17)°, respectively. An intramolecular O–H···O hydrogen bond occurs within the benzylate anion and a S(5) ring (Bernstein et al., 1995) is generated. Moreover, adjacent ion pairs are further extended into an infinite one-dimensional chain along [010] by further intermolecular N—H···O hydrogen bonds (Fig. 2).