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
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.009 Å
- R factor = 0.058
- wR factor = 0.154
- Data-to-parameter ratio = 8.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.00 Ratio PLAT220_ALERT_2_C Large Non-Solvent N Ueq(max)/Ueq(min) ... 2.54 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O7 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O8 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C38 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 8 PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2A ... ? PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2B ... ? PLAT420_ALERT_2_C D-H Without Acceptor N3 - H3B ... ?
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 26.00 From the CIF: _reflns_number_total 4840 Count of symmetry unique reflns 4853 Completeness (_total/calc) 99.73% 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 ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 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 2 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'-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. |
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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).