Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051057/hb2584sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051057/hb2584Isup2.hkl |
CCDC reference: 667403
A 5-ml ethanol solution of 4,4'-oxydianiline (1.0 mmol, 0.20 g) added to 20 ml hot aqueous solution of 2-hydroxy-2,2-diphenylacetic acid (1.0 mmol, 0.23 g) and the mixture was stirred for 15 minutes at 373 K. Then the solution was filtered, and the filtrate was kept at the room temperature. After 5 d, colorless crystals of (I) were obtained.
Anomalous dispersion was negligible and Friedel pairs were merged before refinement.
All the H atoms were placed in calculated positions, with C—H = 0.93 Å, O—H = 0.82 Å, N—H = 0.86 and 0.89 Å for –NH2and –NH3 H atoms, respectively, and were refined as riding with Uiso(H) = 1.2Ueq(C or Namine group) or 1.5Ueq(O or Nprotonated).
This work continues our previous synthetic and structural studies of the hydrogen bonding interactions between the 2-hydroxy-2,2-diphenylacetate anion and substituted pyridinium cations (Li, 2007).
Compound (I) is composed of two pairs of 4,4'-oxydianilinium cations and 2-hydroxy-2,2-diphenylacetate anions, in which each cation interacts with its neighbouring anion by an intermolecular N—H···O hydrogen bond (Fig. 1 and Table 1). In addition, an intramolecular O—H···O bond also occurs in each anion and constructs an S(5) ring. Moreover, adjacent ion pairs are organized into an infinite two-dimensional network running parallel to the plane (001) by further intermolecular N—H···O hydrogen bonds (Fig. 2).
For related literature, see: Li (2007).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (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).
C12H13N2O+·C14H11O3− | F(000) = 904 |
Mr = 428.47 | Dx = 1.258 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 5100 reflections |
a = 14.619 (6) Å | θ = 2.1–28.3° |
b = 6.442 (3) Å | µ = 0.09 mm−1 |
c = 24.938 (10) Å | T = 298 K |
β = 105.499 (7)° | Blade, colourless |
V = 2263.2 (16) Å3 | 0.15 × 0.10 × 0.08 mm |
Z = 4 |
Bruker SMART APEX CCD diffractometer | 4840 independent reflections |
Radiation source: fine-focus sealed tube | 2576 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.068 |
ω scans | θmax = 26.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −18→17 |
Tmin = 0.987, Tmax = 0.993 | k = −7→4 |
12318 measured reflections | l = −29→30 |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.154 | H-atom parameters constrained |
S = 0.84 | w = 1/[σ2(Fo2) + (0.0797P)2] where P = (Fo2 + 2Fc2)/3 |
4840 reflections | (Δ/σ)max < 0.001 |
582 parameters | Δρmax = 0.20 e Å−3 |
1 restraint | Δρmin = −0.17 e Å−3 |
C12H13N2O+·C14H11O3− | V = 2263.2 (16) Å3 |
Mr = 428.47 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 14.619 (6) Å | µ = 0.09 mm−1 |
b = 6.442 (3) Å | T = 298 K |
c = 24.938 (10) Å | 0.15 × 0.10 × 0.08 mm |
β = 105.499 (7)° |
Bruker SMART APEX CCD diffractometer | 4840 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | 2576 reflections with I > 2σ(I) |
Tmin = 0.987, Tmax = 0.993 | Rint = 0.068 |
12318 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | 1 restraint |
wR(F2) = 0.154 | H-atom parameters constrained |
S = 0.84 | Δρmax = 0.20 e Å−3 |
4840 reflections | Δρmin = −0.17 e Å−3 |
582 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 | ||
C1 | 0.2825 (3) | 0.3643 (8) | 0.32307 (18) | 0.0382 (11) | |
C2 | 0.3730 (3) | 0.4688 (7) | 0.35928 (17) | 0.0395 (11) | |
C3 | 0.4293 (3) | 0.5421 (7) | 0.31939 (19) | 0.0397 (12) | |
C4 | 0.4765 (3) | 0.3916 (9) | 0.2954 (2) | 0.0556 (14) | |
H4 | 0.4791 | 0.2547 | 0.3076 | 0.067* | |
C5 | 0.5184 (4) | 0.4447 (10) | 0.2545 (2) | 0.0651 (16) | |
H5 | 0.5490 | 0.3437 | 0.2389 | 0.078* | |
C6 | 0.5156 (4) | 0.6472 (11) | 0.2360 (2) | 0.0630 (16) | |
H6 | 0.5425 | 0.6828 | 0.2074 | 0.076* | |
C7 | 0.4726 (3) | 0.7946 (10) | 0.2603 (2) | 0.0580 (15) | |
H7 | 0.4730 | 0.9321 | 0.2490 | 0.070* | |
C8 | 0.4288 (3) | 0.7449 (8) | 0.30121 (19) | 0.0460 (12) | |
H8 | 0.3989 | 0.8477 | 0.3165 | 0.055* | |
C9 | 0.3496 (4) | 0.6422 (7) | 0.39551 (18) | 0.0448 (12) | |
C10 | 0.4236 (4) | 0.7485 (8) | 0.42978 (19) | 0.0568 (14) | |
H10 | 0.4855 | 0.7172 | 0.4292 | 0.068* | |
C11 | 0.4081 (6) | 0.9000 (10) | 0.4648 (2) | 0.082 (2) | |
H11 | 0.4594 | 0.9669 | 0.4887 | 0.098* | |
C12 | 0.3177 (8) | 0.9535 (11) | 0.4649 (3) | 0.095 (3) | |
H12A | 0.3073 | 1.0618 | 0.4873 | 0.114* | |
C13 | 0.2429 (6) | 0.8474 (10) | 0.4322 (3) | 0.084 (2) | |
H13A | 0.1814 | 0.8793 | 0.4332 | 0.101* | |
C14 | 0.2584 (4) | 0.6913 (8) | 0.3970 (2) | 0.0576 (15) | |
H14 | 0.2072 | 0.6198 | 0.3745 | 0.069* | |
C15 | 0.9588 (3) | −0.1653 (8) | 0.18057 (19) | 0.0411 (12) | |
C16 | 0.8636 (3) | −0.0693 (7) | 0.14776 (18) | 0.0423 (12) | |
C17 | 0.8775 (4) | 0.0975 (8) | 0.10815 (19) | 0.0493 (13) | |
C18 | 0.7976 (5) | 0.2000 (9) | 0.0766 (2) | 0.0727 (18) | |
H18 | 0.7385 | 0.1672 | 0.0816 | 0.087* | |
C19 | 0.8036 (7) | 0.3481 (12) | 0.0384 (3) | 0.102 (3) | |
H19 | 0.7494 | 0.4161 | 0.0179 | 0.123* | |
C20 | 0.8907 (9) | 0.3945 (13) | 0.0308 (3) | 0.121 (4) | |
H20A | 0.8948 | 0.4956 | 0.0050 | 0.145* | |
C21 | 0.9723 (7) | 0.2965 (14) | 0.0602 (3) | 0.113 (3) | |
H21A | 1.0308 | 0.3286 | 0.0542 | 0.136* | |
C22 | 0.9648 (5) | 0.1483 (10) | 0.0992 (3) | 0.0794 (19) | |
H22 | 1.0193 | 0.0814 | 0.1198 | 0.095* | |
C23 | 0.8138 (3) | 0.0002 (7) | 0.19063 (19) | 0.0403 (12) | |
C24 | 0.8126 (3) | 0.2028 (8) | 0.2080 (2) | 0.0467 (13) | |
H24 | 0.8383 | 0.3060 | 0.1904 | 0.056* | |
C25 | 0.7739 (4) | 0.2567 (9) | 0.2512 (2) | 0.0600 (15) | |
H25 | 0.7739 | 0.3948 | 0.2621 | 0.072* | |
C26 | 0.7355 (4) | 0.1064 (11) | 0.2779 (2) | 0.0666 (16) | |
H26 | 0.7093 | 0.1414 | 0.3068 | 0.080* | |
C27 | 0.7365 (4) | −0.0954 (10) | 0.2609 (3) | 0.0679 (17) | |
H27 | 0.7110 | −0.1984 | 0.2788 | 0.081* | |
C28 | 0.7747 (4) | −0.1489 (9) | 0.2179 (2) | 0.0612 (15) | |
H28 | 0.7742 | −0.2870 | 0.2070 | 0.073* | |
C29 | 0.9439 (4) | 0.4522 (10) | 0.3931 (2) | 0.0604 (15) | |
C30 | 0.9793 (4) | 0.2606 (10) | 0.3844 (2) | 0.0672 (17) | |
H30 | 0.9791 | 0.1513 | 0.4087 | 0.081* | |
C31 | 1.0150 (4) | 0.2339 (9) | 0.3388 (2) | 0.0645 (16) | |
H31 | 1.0415 | 0.1068 | 0.3334 | 0.077* | |
C32 | 1.0121 (3) | 0.3899 (8) | 0.3017 (2) | 0.0423 (12) | |
C33 | 0.9784 (3) | 0.5809 (8) | 0.3111 (2) | 0.0527 (14) | |
H33 | 0.9782 | 0.6897 | 0.2866 | 0.063* | |
C34 | 0.9447 (4) | 0.6110 (9) | 0.3571 (2) | 0.0588 (15) | |
H34 | 0.9222 | 0.7410 | 0.3636 | 0.071* | |
C35 | 0.8408 (4) | 0.6235 (10) | 0.4356 (2) | 0.0581 (15) | |
C36 | 0.8631 (4) | 0.8080 (11) | 0.4649 (2) | 0.0716 (18) | |
H36 | 0.9241 | 0.8303 | 0.4876 | 0.086* | |
C37 | 0.7951 (4) | 0.9557 (12) | 0.4603 (2) | 0.0790 (19) | |
H37 | 0.8101 | 1.0779 | 0.4806 | 0.095* | |
C38 | 0.7034 (4) | 0.9295 (11) | 0.4260 (2) | 0.0700 (18) | |
C39 | 0.6839 (4) | 0.7431 (12) | 0.3972 (2) | 0.0719 (19) | |
H39 | 0.6234 | 0.7199 | 0.3741 | 0.086* | |
C40 | 0.7516 (4) | 0.5932 (10) | 0.4020 (2) | 0.0651 (16) | |
H40 | 0.7368 | 0.4698 | 0.3823 | 0.078* | |
C41 | 0.4180 (4) | 0.2114 (9) | 0.0745 (2) | 0.0587 (15) | |
C42 | 0.3848 (4) | 0.3786 (10) | 0.0423 (2) | 0.0637 (16) | |
H42 | 0.3231 | 0.3793 | 0.0194 | 0.076* | |
C43 | 0.4434 (4) | 0.5486 (10) | 0.0436 (2) | 0.0638 (16) | |
H43 | 0.4211 | 0.6628 | 0.0211 | 0.077* | |
C44 | 0.5346 (4) | 0.5498 (10) | 0.0780 (2) | 0.0583 (15) | |
C45 | 0.5667 (4) | 0.3820 (11) | 0.1109 (2) | 0.0656 (16) | |
H45 | 0.6274 | 0.3830 | 0.1352 | 0.079* | |
C46 | 0.5084 (5) | 0.2087 (10) | 0.1081 (2) | 0.0687 (17) | |
H46 | 0.5311 | 0.0913 | 0.1292 | 0.082* | |
C47 | 0.3195 (4) | 0.0073 (9) | 0.1157 (2) | 0.0606 (16) | |
C48 | 0.3129 (4) | 0.1615 (8) | 0.1527 (2) | 0.0537 (14) | |
H48 | 0.3351 | 0.2940 | 0.1483 | 0.064* | |
C49 | 0.2740 (4) | 0.1215 (8) | 0.1956 (2) | 0.0518 (13) | |
H49 | 0.2703 | 0.2261 | 0.2206 | 0.062* | |
C50 | 0.2403 (3) | −0.0742 (7) | 0.20173 (19) | 0.0416 (12) | |
C51 | 0.2414 (4) | −0.2238 (9) | 0.1636 (2) | 0.0589 (15) | |
H51 | 0.2153 | −0.3534 | 0.1666 | 0.071* | |
C52 | 0.2815 (5) | −0.1844 (9) | 0.1201 (2) | 0.0701 (17) | |
H52 | 0.2826 | −0.2873 | 0.0941 | 0.084* | |
N1 | 1.0460 (3) | 0.3568 (6) | 0.25262 (16) | 0.0466 (10) | |
H1A | 1.1086 | 0.3742 | 0.2614 | 0.070* | |
H1B | 1.0184 | 0.4476 | 0.2264 | 0.070* | |
H1C | 1.0317 | 0.2284 | 0.2400 | 0.070* | |
N2 | 0.6361 (4) | 1.0889 (11) | 0.4196 (3) | 0.119 (2) | |
H2A | 0.6511 | 1.2045 | 0.4370 | 0.143* | |
H2B | 0.5797 | 1.0711 | 0.3983 | 0.143* | |
N3 | 0.5907 (4) | 0.7274 (9) | 0.0817 (2) | 0.0833 (16) | |
H3A | 0.6461 | 0.7316 | 0.1049 | 0.100* | |
H3B | 0.5699 | 0.8327 | 0.0607 | 0.100* | |
N4 | 0.2020 (2) | −0.1196 (6) | 0.24908 (15) | 0.0420 (10) | |
H4A | 0.2232 | −0.0258 | 0.2757 | 0.063* | |
H4B | 0.2207 | −0.2456 | 0.2622 | 0.063* | |
H4C | 0.1389 | −0.1152 | 0.2381 | 0.063* | |
O1 | 0.2287 (2) | 0.4743 (5) | 0.28538 (12) | 0.0421 (8) | |
O2 | 0.2690 (2) | 0.1789 (5) | 0.33123 (14) | 0.0567 (9) | |
O3 | 0.4277 (2) | 0.3158 (6) | 0.39477 (15) | 0.0605 (10) | |
H3 | 0.3970 | 0.2079 | 0.3921 | 0.091* | |
O4 | 0.9744 (3) | −0.3488 (5) | 0.17179 (14) | 0.0592 (10) | |
O5 | 1.0144 (2) | −0.0501 (5) | 0.21549 (13) | 0.0469 (8) | |
O6 | 0.8082 (2) | −0.2314 (6) | 0.11509 (16) | 0.0624 (10) | |
H6A | 0.8432 | −0.3276 | 0.1119 | 0.094* | |
O7 | 0.9104 (3) | 0.4712 (7) | 0.43911 (15) | 0.0776 (12) | |
O8 | 0.3592 (3) | 0.0372 (7) | 0.07231 (16) | 0.0867 (14) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.044 (3) | 0.036 (3) | 0.039 (3) | 0.001 (2) | 0.019 (2) | −0.002 (2) |
C2 | 0.043 (3) | 0.031 (3) | 0.040 (2) | −0.005 (2) | 0.003 (2) | 0.007 (2) |
C3 | 0.034 (3) | 0.038 (3) | 0.044 (3) | −0.002 (2) | 0.005 (2) | 0.001 (2) |
C4 | 0.051 (3) | 0.043 (3) | 0.074 (4) | −0.002 (3) | 0.020 (3) | −0.001 (3) |
C5 | 0.055 (4) | 0.066 (5) | 0.080 (4) | 0.004 (3) | 0.027 (3) | −0.007 (4) |
C6 | 0.048 (3) | 0.082 (5) | 0.065 (4) | 0.001 (3) | 0.027 (3) | −0.001 (3) |
C7 | 0.052 (3) | 0.059 (4) | 0.066 (3) | −0.003 (3) | 0.021 (3) | 0.008 (3) |
C8 | 0.039 (3) | 0.048 (3) | 0.049 (3) | −0.001 (2) | 0.007 (2) | −0.001 (3) |
C9 | 0.064 (3) | 0.033 (3) | 0.036 (3) | −0.011 (3) | 0.011 (3) | 0.003 (2) |
C10 | 0.079 (4) | 0.046 (4) | 0.040 (3) | −0.015 (3) | 0.007 (3) | 0.000 (3) |
C11 | 0.146 (7) | 0.058 (5) | 0.041 (3) | −0.025 (4) | 0.025 (4) | −0.014 (3) |
C12 | 0.191 (9) | 0.053 (4) | 0.057 (4) | 0.000 (5) | 0.063 (5) | −0.014 (4) |
C13 | 0.129 (6) | 0.059 (5) | 0.082 (4) | 0.009 (4) | 0.059 (5) | −0.009 (4) |
C14 | 0.082 (4) | 0.044 (3) | 0.053 (3) | −0.006 (3) | 0.030 (3) | −0.010 (3) |
C15 | 0.050 (3) | 0.031 (3) | 0.044 (3) | 0.002 (2) | 0.016 (2) | −0.001 (2) |
C16 | 0.045 (3) | 0.036 (3) | 0.044 (3) | −0.002 (2) | 0.008 (2) | 0.000 (2) |
C17 | 0.071 (4) | 0.035 (3) | 0.038 (3) | 0.009 (3) | 0.008 (3) | 0.000 (2) |
C18 | 0.101 (5) | 0.055 (4) | 0.049 (3) | 0.012 (4) | −0.004 (3) | −0.001 (3) |
C19 | 0.166 (8) | 0.071 (6) | 0.055 (4) | 0.026 (6) | 0.004 (5) | 0.009 (4) |
C20 | 0.228 (12) | 0.065 (6) | 0.076 (5) | 0.018 (7) | 0.053 (7) | 0.029 (4) |
C21 | 0.166 (8) | 0.093 (6) | 0.103 (6) | −0.001 (6) | 0.076 (6) | 0.016 (5) |
C22 | 0.100 (5) | 0.073 (5) | 0.076 (4) | 0.012 (4) | 0.042 (4) | 0.016 (4) |
C23 | 0.031 (3) | 0.036 (3) | 0.052 (3) | 0.004 (2) | 0.008 (2) | 0.001 (2) |
C24 | 0.040 (3) | 0.044 (3) | 0.053 (3) | −0.004 (2) | 0.008 (2) | 0.000 (3) |
C25 | 0.060 (4) | 0.054 (4) | 0.067 (4) | −0.002 (3) | 0.018 (3) | −0.006 (3) |
C26 | 0.058 (4) | 0.077 (5) | 0.071 (4) | 0.005 (3) | 0.028 (3) | −0.004 (4) |
C27 | 0.061 (4) | 0.065 (5) | 0.085 (4) | −0.004 (3) | 0.034 (3) | 0.013 (4) |
C28 | 0.060 (4) | 0.050 (4) | 0.076 (4) | −0.009 (3) | 0.024 (3) | −0.002 (3) |
C29 | 0.064 (4) | 0.070 (4) | 0.050 (3) | 0.006 (3) | 0.020 (3) | 0.007 (3) |
C30 | 0.093 (5) | 0.049 (4) | 0.060 (4) | 0.015 (3) | 0.020 (3) | 0.021 (3) |
C31 | 0.073 (4) | 0.047 (4) | 0.073 (4) | 0.019 (3) | 0.019 (3) | 0.012 (3) |
C32 | 0.036 (3) | 0.035 (3) | 0.054 (3) | 0.001 (2) | 0.007 (2) | 0.002 (3) |
C33 | 0.059 (3) | 0.035 (3) | 0.066 (4) | 0.001 (3) | 0.020 (3) | 0.006 (3) |
C34 | 0.073 (4) | 0.041 (3) | 0.067 (4) | 0.007 (3) | 0.027 (3) | −0.001 (3) |
C35 | 0.060 (4) | 0.071 (4) | 0.046 (3) | 0.005 (3) | 0.018 (3) | 0.006 (3) |
C36 | 0.051 (4) | 0.092 (5) | 0.065 (4) | 0.003 (4) | 0.005 (3) | −0.017 (4) |
C37 | 0.074 (5) | 0.081 (5) | 0.079 (4) | 0.001 (4) | 0.015 (4) | −0.029 (4) |
C38 | 0.062 (4) | 0.090 (5) | 0.065 (4) | 0.015 (4) | 0.028 (3) | 0.003 (4) |
C39 | 0.056 (4) | 0.103 (6) | 0.057 (4) | −0.019 (4) | 0.015 (3) | −0.019 (4) |
C40 | 0.074 (4) | 0.070 (4) | 0.059 (4) | −0.010 (4) | 0.032 (3) | −0.008 (3) |
C41 | 0.081 (4) | 0.058 (4) | 0.041 (3) | −0.011 (3) | 0.025 (3) | −0.007 (3) |
C42 | 0.061 (4) | 0.081 (5) | 0.048 (3) | −0.009 (3) | 0.013 (3) | −0.004 (3) |
C43 | 0.069 (4) | 0.071 (4) | 0.050 (3) | −0.001 (3) | 0.013 (3) | 0.012 (3) |
C44 | 0.065 (4) | 0.067 (4) | 0.047 (3) | −0.001 (3) | 0.020 (3) | −0.005 (3) |
C45 | 0.063 (4) | 0.076 (5) | 0.056 (3) | 0.009 (4) | 0.013 (3) | −0.003 (3) |
C46 | 0.101 (5) | 0.056 (4) | 0.050 (3) | 0.018 (4) | 0.021 (4) | 0.009 (3) |
C47 | 0.087 (4) | 0.056 (4) | 0.044 (3) | −0.021 (3) | 0.027 (3) | −0.014 (3) |
C48 | 0.079 (4) | 0.041 (3) | 0.048 (3) | −0.012 (3) | 0.028 (3) | 0.002 (3) |
C49 | 0.071 (4) | 0.029 (3) | 0.057 (3) | −0.001 (3) | 0.020 (3) | −0.009 (3) |
C50 | 0.045 (3) | 0.032 (3) | 0.045 (3) | −0.004 (2) | 0.005 (2) | −0.004 (2) |
C51 | 0.078 (4) | 0.043 (3) | 0.060 (3) | −0.021 (3) | 0.025 (3) | −0.011 (3) |
C52 | 0.108 (5) | 0.043 (4) | 0.063 (4) | −0.017 (3) | 0.029 (4) | −0.020 (3) |
N1 | 0.041 (2) | 0.036 (2) | 0.063 (3) | 0.0039 (19) | 0.013 (2) | −0.003 (2) |
N2 | 0.100 (5) | 0.104 (5) | 0.158 (6) | 0.039 (4) | 0.044 (4) | 0.001 (5) |
N3 | 0.078 (4) | 0.082 (4) | 0.087 (4) | −0.025 (3) | 0.016 (3) | −0.001 (3) |
N4 | 0.038 (2) | 0.034 (2) | 0.055 (2) | −0.0003 (17) | 0.0143 (18) | 0.003 (2) |
O1 | 0.0451 (19) | 0.0297 (19) | 0.0488 (18) | −0.0006 (15) | 0.0081 (16) | 0.0045 (16) |
O2 | 0.075 (2) | 0.030 (2) | 0.061 (2) | −0.0153 (17) | 0.0114 (19) | 0.0040 (18) |
O3 | 0.060 (2) | 0.044 (2) | 0.065 (2) | 0.0040 (18) | −0.0052 (19) | 0.016 (2) |
O4 | 0.078 (3) | 0.027 (2) | 0.068 (2) | 0.0149 (18) | 0.012 (2) | −0.0037 (18) |
O5 | 0.0371 (18) | 0.043 (2) | 0.057 (2) | −0.0013 (16) | 0.0064 (16) | −0.0092 (18) |
O6 | 0.056 (2) | 0.047 (2) | 0.075 (2) | −0.0053 (18) | 0.0023 (19) | −0.023 (2) |
O7 | 0.098 (3) | 0.082 (3) | 0.060 (2) | 0.027 (3) | 0.034 (2) | 0.019 (2) |
O8 | 0.140 (4) | 0.076 (3) | 0.059 (2) | −0.042 (3) | 0.052 (3) | −0.026 (2) |
C1—O2 | 1.236 (5) | C29—C30 | 1.378 (8) |
C1—O1 | 1.269 (5) | C30—C31 | 1.383 (7) |
C1—C2 | 1.543 (6) | C30—H30 | 0.9300 |
C2—O3 | 1.420 (5) | C31—C32 | 1.358 (7) |
C2—C3 | 1.525 (6) | C31—H31 | 0.9300 |
C2—C9 | 1.532 (7) | C32—C33 | 1.369 (7) |
C3—C8 | 1.382 (6) | C32—N1 | 1.454 (6) |
C3—C4 | 1.412 (7) | C33—C34 | 1.376 (7) |
C4—C5 | 1.367 (7) | C33—H33 | 0.9300 |
C4—H4 | 0.9300 | C34—H34 | 0.9300 |
C5—C6 | 1.381 (9) | C35—C40 | 1.362 (7) |
C5—H5 | 0.9300 | C35—C36 | 1.388 (8) |
C6—C7 | 1.367 (8) | C35—O7 | 1.398 (7) |
C6—H6 | 0.9300 | C36—C37 | 1.359 (8) |
C7—C8 | 1.380 (7) | C36—H36 | 0.9300 |
C7—H7 | 0.9300 | C37—C38 | 1.394 (8) |
C8—H8 | 0.9300 | C37—H37 | 0.9300 |
C9—C10 | 1.370 (7) | C38—N2 | 1.402 (8) |
C9—C14 | 1.380 (7) | C38—C39 | 1.389 (9) |
C10—C11 | 1.368 (8) | C39—C40 | 1.365 (8) |
C10—H10 | 0.9300 | C39—H39 | 0.9300 |
C11—C12 | 1.367 (10) | C40—H40 | 0.9300 |
C11—H11 | 0.9300 | C41—C42 | 1.353 (8) |
C12—C13 | 1.361 (10) | C41—C46 | 1.362 (8) |
C12—H12A | 0.9300 | C41—O8 | 1.407 (7) |
C13—C14 | 1.392 (7) | C42—C43 | 1.386 (8) |
C13—H13A | 0.9300 | C42—H42 | 0.9300 |
C14—H14 | 0.9300 | C43—C44 | 1.380 (7) |
C15—O4 | 1.235 (5) | C43—H43 | 0.9300 |
C15—O5 | 1.262 (6) | C44—C45 | 1.362 (8) |
C15—C16 | 1.542 (6) | C44—N3 | 1.397 (7) |
C16—O6 | 1.434 (6) | C45—C46 | 1.396 (8) |
C16—C17 | 1.510 (7) | C45—H45 | 0.9300 |
C16—C23 | 1.514 (6) | C46—H46 | 0.9300 |
C17—C18 | 1.388 (7) | C47—O8 | 1.371 (6) |
C17—C22 | 1.392 (8) | C47—C52 | 1.371 (8) |
C18—C19 | 1.367 (9) | C47—C48 | 1.376 (7) |
C18—H18 | 0.9300 | C48—C49 | 1.364 (6) |
C19—C20 | 1.369 (11) | C48—H48 | 0.9300 |
C19—H19 | 0.9300 | C49—C50 | 1.377 (7) |
C20—C21 | 1.376 (12) | C49—H49 | 0.9300 |
C20—H20A | 0.9300 | C50—C51 | 1.358 (7) |
C21—C22 | 1.387 (9) | C50—N4 | 1.465 (5) |
C21—H21A | 0.9300 | C51—C52 | 1.387 (7) |
C22—H22 | 0.9300 | C51—H51 | 0.9300 |
C23—C24 | 1.377 (7) | C52—H52 | 0.9300 |
C23—C28 | 1.384 (7) | N1—H1A | 0.8900 |
C24—C25 | 1.387 (7) | N1—H1B | 0.8900 |
C24—H24 | 0.9300 | N1—H1C | 0.8900 |
C25—C26 | 1.377 (8) | N2—H2A | 0.8600 |
C25—H25 | 0.9300 | N2—H2B | 0.8600 |
C26—C27 | 1.368 (8) | N3—H3A | 0.8600 |
C26—H26 | 0.9300 | N3—H3B | 0.8600 |
C27—C28 | 1.380 (7) | N4—H4A | 0.8900 |
C27—H27 | 0.9300 | N4—H4B | 0.8900 |
C28—H28 | 0.9300 | N4—H4C | 0.8900 |
C29—C34 | 1.364 (8) | O3—H3 | 0.8200 |
C29—O7 | 1.368 (6) | O6—H6A | 0.8200 |
O2—C1—O1 | 124.5 (4) | O7—C29—C30 | 116.5 (5) |
O2—C1—C2 | 118.4 (4) | C29—C30—C31 | 118.8 (5) |
O1—C1—C2 | 117.0 (4) | C29—C30—H30 | 120.6 |
O3—C2—C3 | 108.1 (4) | C31—C30—H30 | 120.6 |
O3—C2—C9 | 108.4 (4) | C32—C31—C30 | 121.1 (5) |
C3—C2—C9 | 113.8 (4) | C32—C31—H31 | 119.4 |
O3—C2—C1 | 108.2 (4) | C30—C31—H31 | 119.4 |
C3—C2—C1 | 106.3 (3) | C31—C32—C33 | 119.7 (5) |
C9—C2—C1 | 111.8 (4) | C31—C32—N1 | 120.6 (4) |
C8—C3—C4 | 118.1 (4) | C33—C32—N1 | 119.7 (4) |
C8—C3—C2 | 123.3 (4) | C34—C33—C32 | 119.7 (5) |
C4—C3—C2 | 118.2 (4) | C34—C33—H33 | 120.2 |
C5—C4—C3 | 120.7 (5) | C32—C33—H33 | 120.2 |
C5—C4—H4 | 119.6 | C29—C34—C33 | 120.7 (5) |
C3—C4—H4 | 119.6 | C29—C34—H34 | 119.6 |
C4—C5—C6 | 120.4 (6) | C33—C34—H34 | 119.6 |
C4—C5—H5 | 119.8 | C40—C35—C36 | 119.9 (6) |
C6—C5—H5 | 119.8 | C40—C35—O7 | 119.9 (6) |
C7—C6—C5 | 119.0 (5) | C36—C35—O7 | 120.2 (5) |
C7—C6—H6 | 120.5 | C37—C36—C35 | 119.4 (5) |
C5—C6—H6 | 120.5 | C37—C36—H36 | 120.3 |
C6—C7—C8 | 121.8 (6) | C35—C36—H36 | 120.3 |
C6—C7—H7 | 119.1 | C36—C37—C38 | 121.9 (6) |
C8—C7—H7 | 119.1 | C36—C37—H37 | 119.0 |
C7—C8—C3 | 119.9 (5) | C38—C37—H37 | 119.0 |
C7—C8—H8 | 120.0 | C37—C38—N2 | 120.8 (7) |
C3—C8—H8 | 120.0 | C37—C38—C39 | 116.9 (6) |
C10—C9—C14 | 118.4 (5) | N2—C38—C39 | 122.3 (6) |
C10—C9—C2 | 117.9 (5) | C40—C39—C38 | 121.4 (6) |
C14—C9—C2 | 123.6 (4) | C40—C39—H39 | 119.3 |
C9—C10—C11 | 121.1 (6) | C38—C39—H39 | 119.3 |
C9—C10—H10 | 119.4 | C35—C40—C39 | 120.4 (6) |
C11—C10—H10 | 119.4 | C35—C40—H40 | 119.8 |
C12—C11—C10 | 120.4 (6) | C39—C40—H40 | 119.8 |
C12—C11—H11 | 119.8 | C42—C41—C46 | 120.7 (6) |
C10—C11—H11 | 119.8 | C42—C41—O8 | 119.6 (6) |
C11—C12—C13 | 119.6 (6) | C46—C41—O8 | 119.7 (6) |
C11—C12—H12A | 120.2 | C41—C42—C43 | 119.6 (6) |
C13—C12—H12A | 120.2 | C41—C42—H42 | 120.2 |
C12—C13—C14 | 120.1 (7) | C43—C42—H42 | 120.2 |
C12—C13—H13A | 120.0 | C44—C43—C42 | 120.5 (6) |
C14—C13—H13A | 120.0 | C44—C43—H43 | 119.8 |
C9—C14—C13 | 120.3 (6) | C42—C43—H43 | 119.8 |
C9—C14—H14 | 119.9 | C45—C44—C43 | 119.4 (6) |
C13—C14—H14 | 119.9 | C45—C44—N3 | 120.6 (5) |
O4—C15—O5 | 124.8 (5) | C43—C44—N3 | 119.9 (6) |
O4—C15—C16 | 118.2 (5) | C44—C45—C46 | 119.8 (6) |
O5—C15—C16 | 117.0 (4) | C44—C45—H45 | 120.1 |
O6—C16—C17 | 107.5 (4) | C46—C45—H45 | 120.1 |
O6—C16—C23 | 108.2 (4) | C41—C46—C45 | 120.0 (6) |
C17—C16—C23 | 115.2 (4) | C41—C46—H46 | 120.0 |
O6—C16—C15 | 107.6 (4) | C45—C46—H46 | 120.0 |
C17—C16—C15 | 111.9 (4) | O8—C47—C52 | 117.1 (5) |
C23—C16—C15 | 106.3 (3) | O8—C47—C48 | 123.2 (5) |
C18—C17—C22 | 117.8 (5) | C52—C47—C48 | 119.6 (5) |
C18—C17—C16 | 118.0 (5) | C49—C48—C47 | 120.6 (5) |
C22—C17—C16 | 124.2 (5) | C49—C48—H48 | 119.7 |
C19—C18—C17 | 121.8 (7) | C47—C48—H48 | 119.7 |
C19—C18—H18 | 119.1 | C48—C49—C50 | 119.8 (5) |
C17—C18—H18 | 119.1 | C48—C49—H49 | 120.1 |
C20—C19—C18 | 118.9 (8) | C50—C49—H49 | 120.1 |
C20—C19—H19 | 120.5 | C51—C50—C49 | 120.0 (5) |
C18—C19—H19 | 120.5 | C51—C50—N4 | 120.1 (4) |
C19—C20—C21 | 122.2 (8) | C49—C50—N4 | 119.9 (4) |
C19—C20—H20A | 118.9 | C50—C51—C52 | 120.3 (5) |
C21—C20—H20A | 118.9 | C50—C51—H51 | 119.8 |
C20—C21—C22 | 118.0 (8) | C52—C51—H51 | 119.8 |
C20—C21—H21A | 121.0 | C47—C52—C51 | 119.5 (5) |
C22—C21—H21A | 121.0 | C47—C52—H52 | 120.3 |
C17—C22—C21 | 121.4 (7) | C51—C52—H52 | 120.3 |
C17—C22—H22 | 119.3 | C32—N1—H1A | 109.5 |
C21—C22—H22 | 119.3 | C32—N1—H1B | 109.5 |
C24—C23—C28 | 117.5 (5) | H1A—N1—H1B | 109.5 |
C24—C23—C16 | 123.5 (4) | C32—N1—H1C | 109.5 |
C28—C23—C16 | 118.7 (4) | H1A—N1—H1C | 109.5 |
C23—C24—C25 | 121.6 (5) | H1B—N1—H1C | 109.5 |
C23—C24—H24 | 119.2 | C38—N2—H2A | 120.0 |
C25—C24—H24 | 119.2 | C38—N2—H2B | 120.0 |
C26—C25—C24 | 120.1 (6) | H2A—N2—H2B | 120.0 |
C26—C25—H25 | 119.9 | C44—N3—H3A | 120.0 |
C24—C25—H25 | 119.9 | C44—N3—H3B | 120.0 |
C27—C26—C25 | 118.7 (5) | H3A—N3—H3B | 120.0 |
C27—C26—H26 | 120.7 | C50—N4—H4A | 109.5 |
C25—C26—H26 | 120.7 | C50—N4—H4B | 109.5 |
C26—C27—C28 | 121.1 (5) | H4A—N4—H4B | 109.5 |
C26—C27—H27 | 119.4 | C50—N4—H4C | 109.5 |
C28—C27—H27 | 119.4 | H4A—N4—H4C | 109.5 |
C27—C28—C23 | 121.0 (5) | H4B—N4—H4C | 109.5 |
C27—C28—H28 | 119.5 | C2—O3—H3 | 109.5 |
C23—C28—H28 | 119.5 | C16—O6—H6A | 109.5 |
C34—C29—O7 | 123.6 (6) | C29—O7—C35 | 115.3 (4) |
C34—C29—C30 | 119.9 (5) | C47—O8—C41 | 117.7 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6A···O4 | 0.82 | 2.10 | 2.576 (5) | 117 |
O3—H3···O2 | 0.82 | 2.08 | 2.589 (5) | 120 |
N4—H4C···O5i | 0.89 | 1.81 | 2.683 (5) | 168 |
N4—H4B···O1ii | 0.89 | 1.89 | 2.761 (5) | 166 |
N4—H4A···O2 | 0.89 | 1.90 | 2.790 (5) | 179 |
N3—H3A···O6iii | 0.86 | 2.33 | 3.076 (6) | 146 |
N1—H1C···O5 | 0.89 | 1.89 | 2.777 (5) | 174 |
N1—H1B···O4iii | 0.89 | 1.88 | 2.762 (5) | 173 |
N1—H1A···O1iv | 0.89 | 1.81 | 2.685 (5) | 165 |
Symmetry codes: (i) x−1, y, z; (ii) x, y−1, z; (iii) x, y+1, z; (iv) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C12H13N2O+·C14H11O3− |
Mr | 428.47 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 298 |
a, b, c (Å) | 14.619 (6), 6.442 (3), 24.938 (10) |
β (°) | 105.499 (7) |
V (Å3) | 2263.2 (16) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.15 × 0.10 × 0.08 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2001) |
Tmin, Tmax | 0.987, 0.993 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12318, 4840, 2576 |
Rint | 0.068 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.154, 0.84 |
No. of reflections | 4840 |
No. of parameters | 582 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.17 |
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 |
O6—H6A···O4 | 0.82 | 2.10 | 2.576 (5) | 117 |
O3—H3···O2 | 0.82 | 2.08 | 2.589 (5) | 120 |
N4—H4C···O5i | 0.89 | 1.81 | 2.683 (5) | 168 |
N4—H4B···O1ii | 0.89 | 1.89 | 2.761 (5) | 166 |
N4—H4A···O2 | 0.89 | 1.90 | 2.790 (5) | 179 |
N3—H3A···O6iii | 0.86 | 2.33 | 3.076 (6) | 146 |
N1—H1C···O5 | 0.89 | 1.89 | 2.777 (5) | 174 |
N1—H1B···O4iii | 0.89 | 1.88 | 2.762 (5) | 173 |
N1—H1A···O1iv | 0.89 | 1.81 | 2.685 (5) | 165 |
Symmetry codes: (i) x−1, y, z; (ii) x, y−1, z; (iii) x, y+1, z; (iv) x+1, y, z. |
This work continues our previous synthetic and structural studies of the hydrogen bonding interactions between the 2-hydroxy-2,2-diphenylacetate anion and substituted pyridinium cations (Li, 2007).
Compound (I) is composed of two pairs of 4,4'-oxydianilinium cations and 2-hydroxy-2,2-diphenylacetate anions, in which each cation interacts with its neighbouring anion by an intermolecular N—H···O hydrogen bond (Fig. 1 and Table 1). In addition, an intramolecular O—H···O bond also occurs in each anion and constructs an S(5) ring. Moreover, adjacent ion pairs are organized into an infinite two-dimensional network running parallel to the plane (001) by further intermolecular N—H···O hydrogen bonds (Fig. 2).