Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807048994/hb2569sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807048994/hb2569Isup2.hkl |
CCDC reference: 667348
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.045
- wR factor = 0.121
- Data-to-parameter ratio = 11.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT731_ALERT_1_C Bond Calc 0.83(3), Rep 0.825(10) ...... 3.00 su-Ra O5 -H5B 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.83(3), Rep 0.825(10) ...... 3.00 su-Ra O5 -H5B 1.555 1.555
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
A 5-ml ethanol soloution of (1,1'-biphenyl)-4,4'-diamine (0.5 mmol, 0.090 g) was added to an aqueous solution (20 ml) of 2-nitrobenzoic acid (1.0 mmol, 0.210 g). The mixture was stirred for 10 minutes at 373 K. The solution was filtered, and the filtrate was kept at the room temperature. After 3 d, colourless blocks of (I) were obtained.
The water H atoms were located in a difference map and refined isotropically with O—H = 0.82 (1) Å and H···H = 1.34 (1) Å. All remaining H atoms were positioned geometrically with C—H = 0.93 Å and N—H = 0.89 Å, and refined as riding with Uiso(H) = 1.2Ueq(C, N).
This work continues our previous synthetic and structural studies of supramolecular salts (Wei, 2007). Herein we present the crystal structure of the title salt, (I).
The title salt contains one (1,1'-biphenyl)-4,4'-diammonium dication (with the complete molecule generated from the asymmetry atoms by 2-fold symmetry), one 2-nitrobenzoate anion and one crystallization water molecule (Fig. 1). Interestingly, these components are organized into an infinite two-dimensional network in (100) via intermolecular N—H···O and O—H···O hydrogen bonds (Table 1). Further hydrogen bonds link the planes into an infinite three-dimensional framework (Fig. 2).
For related literature, see: Wei (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.
C12H14N22+·2C7H4NO4−·2H2O | F(000) = 1160 |
Mr = 554.51 | Dx = 1.474 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 2540 reflections |
a = 29.411 (10) Å | θ = 2.3–27.8° |
b = 6.731 (6) Å | µ = 0.12 mm−1 |
c = 13.511 (6) Å | T = 298 K |
β = 110.91 (2)° | Block, colorless |
V = 2499 (3) Å3 | 0.15 × 0.10 × 0.08 mm |
Z = 4 |
Bruker SMART APEX CCD diffractometer | 2185 independent reflections |
Radiation source: fine-focus sealed tube | 1386 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.062 |
ω scans | θmax = 25.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −34→34 |
Tmin = 0.983, Tmax = 0.991 | k = −8→4 |
5946 measured reflections | l = −15→16 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difmap and geom |
R[F2 > 2σ(F2)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.121 | w = 1/[σ2(Fo2) + (0.0609P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.96 | (Δ/σ)max < 0.001 |
2185 reflections | Δρmax = 0.20 e Å−3 |
190 parameters | Δρmin = −0.20 e Å−3 |
3 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0029 (5) |
C12H14N22+·2C7H4NO4−·2H2O | V = 2499 (3) Å3 |
Mr = 554.51 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 29.411 (10) Å | µ = 0.12 mm−1 |
b = 6.731 (6) Å | T = 298 K |
c = 13.511 (6) Å | 0.15 × 0.10 × 0.08 mm |
β = 110.91 (2)° |
Bruker SMART APEX CCD diffractometer | 2185 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | 1386 reflections with I > 2σ(I) |
Tmin = 0.983, Tmax = 0.991 | Rint = 0.062 |
5946 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 3 restraints |
wR(F2) = 0.121 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.96 | Δρmax = 0.20 e Å−3 |
2185 reflections | Δρmin = −0.20 e Å−3 |
190 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 | ||
N2 | 0.17925 (6) | 0.6702 (3) | 0.43129 (13) | 0.0362 (5) | |
H2A | 0.1883 | 0.7790 | 0.4709 | 0.043* | |
H2B | 0.1879 | 0.5631 | 0.4724 | 0.043* | |
H2C | 0.1937 | 0.6678 | 0.3836 | 0.043* | |
C8 | 0.02670 (7) | 0.6736 (3) | 0.27712 (15) | 0.0317 (5) | |
C9 | 0.04800 (8) | 0.6479 (3) | 0.38501 (16) | 0.0395 (6) | |
H9 | 0.0282 | 0.6307 | 0.4249 | 0.047* | |
C10 | 0.09734 (7) | 0.6471 (3) | 0.43505 (17) | 0.0399 (6) | |
H10 | 0.1108 | 0.6308 | 0.5081 | 0.048* | |
C11 | 0.12677 (7) | 0.6702 (3) | 0.37748 (15) | 0.0301 (5) | |
C12 | 0.10755 (8) | 0.6939 (3) | 0.27140 (16) | 0.0380 (5) | |
H12 | 0.1278 | 0.7076 | 0.2324 | 0.046* | |
C13 | 0.05784 (7) | 0.6975 (3) | 0.22153 (17) | 0.0391 (6) | |
H13 | 0.0448 | 0.7165 | 0.1486 | 0.047* | |
O1 | 0.20236 (5) | 0.0065 (2) | 0.55407 (10) | 0.0438 (4) | |
O2 | 0.20105 (5) | 0.3356 (2) | 0.55937 (11) | 0.0422 (4) | |
O3 | 0.10450 (6) | 0.1729 (3) | 0.54010 (12) | 0.0624 (5) | |
O4 | 0.03547 (6) | 0.1668 (3) | 0.41844 (13) | 0.0690 (6) | |
N1 | 0.07935 (6) | 0.1705 (3) | 0.44818 (14) | 0.0384 (5) | |
C1 | 0.15299 (7) | 0.1746 (3) | 0.40264 (15) | 0.0290 (5) | |
C2 | 0.10279 (7) | 0.1757 (3) | 0.36982 (15) | 0.0298 (5) | |
C3 | 0.07362 (7) | 0.1805 (3) | 0.26614 (15) | 0.0354 (5) | |
H3 | 0.0399 | 0.1823 | 0.2468 | 0.042* | |
C4 | 0.09457 (8) | 0.1827 (3) | 0.19041 (16) | 0.0425 (6) | |
H4 | 0.0751 | 0.1864 | 0.1190 | 0.051* | |
C5 | 0.14405 (8) | 0.1796 (3) | 0.21997 (17) | 0.0455 (6) | |
H5 | 0.1582 | 0.1794 | 0.1684 | 0.055* | |
C6 | 0.17296 (7) | 0.1768 (3) | 0.32460 (16) | 0.0384 (5) | |
H6 | 0.2066 | 0.1763 | 0.3435 | 0.046* | |
C7 | 0.18748 (7) | 0.1723 (3) | 0.51510 (15) | 0.0327 (5) | |
O5 | 0.22537 (7) | 0.3304 (3) | 0.78346 (15) | 0.0677 (6) | |
H5A | 0.2185 (10) | 0.337 (5) | 0.7192 (8) | 0.105 (13)* | |
H5B | 0.2483 (8) | 0.406 (4) | 0.8133 (17) | 0.099 (12)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N2 | 0.0350 (10) | 0.0391 (10) | 0.0321 (10) | 0.0017 (8) | 0.0091 (8) | 0.0001 (8) |
C8 | 0.0355 (11) | 0.0287 (11) | 0.0308 (11) | 0.0001 (9) | 0.0118 (9) | −0.0007 (10) |
C9 | 0.0386 (12) | 0.0512 (14) | 0.0318 (12) | 0.0013 (11) | 0.0164 (10) | −0.0006 (11) |
C10 | 0.0397 (13) | 0.0501 (15) | 0.0270 (11) | 0.0038 (11) | 0.0084 (10) | −0.0017 (10) |
C11 | 0.0308 (11) | 0.0244 (11) | 0.0313 (11) | 0.0010 (9) | 0.0066 (9) | 0.0002 (9) |
C12 | 0.0351 (12) | 0.0457 (14) | 0.0351 (12) | 0.0000 (10) | 0.0146 (10) | 0.0062 (11) |
C13 | 0.0382 (13) | 0.0470 (14) | 0.0295 (11) | −0.0006 (11) | 0.0087 (10) | 0.0030 (10) |
O1 | 0.0495 (9) | 0.0399 (10) | 0.0303 (8) | 0.0061 (8) | 0.0000 (7) | 0.0033 (7) |
O2 | 0.0475 (9) | 0.0372 (9) | 0.0318 (8) | −0.0027 (7) | 0.0016 (7) | −0.0023 (7) |
O3 | 0.0518 (10) | 0.1070 (16) | 0.0290 (9) | 0.0001 (10) | 0.0155 (8) | 0.0046 (10) |
O4 | 0.0327 (10) | 0.1222 (17) | 0.0561 (11) | −0.0020 (10) | 0.0209 (8) | 0.0071 (11) |
N1 | 0.0352 (11) | 0.0479 (12) | 0.0340 (11) | 0.0011 (9) | 0.0144 (9) | 0.0027 (9) |
C1 | 0.0319 (11) | 0.0280 (11) | 0.0249 (10) | 0.0011 (9) | 0.0076 (9) | 0.0001 (9) |
C2 | 0.0322 (11) | 0.0307 (11) | 0.0272 (11) | 0.0012 (9) | 0.0116 (9) | −0.0007 (9) |
C3 | 0.0298 (11) | 0.0387 (12) | 0.0327 (12) | 0.0026 (10) | 0.0050 (9) | 0.0000 (10) |
C4 | 0.0427 (13) | 0.0547 (15) | 0.0252 (11) | 0.0080 (12) | 0.0061 (10) | 0.0020 (11) |
C5 | 0.0473 (14) | 0.0613 (16) | 0.0320 (12) | 0.0053 (12) | 0.0190 (11) | 0.0011 (12) |
C6 | 0.0294 (11) | 0.0512 (14) | 0.0345 (12) | 0.0038 (11) | 0.0114 (10) | 0.0015 (11) |
C7 | 0.0313 (11) | 0.0376 (13) | 0.0276 (11) | 0.0002 (11) | 0.0088 (9) | −0.0001 (11) |
O5 | 0.0542 (12) | 0.1079 (17) | 0.0425 (11) | −0.0330 (12) | 0.0192 (9) | −0.0181 (11) |
N2—C11 | 1.453 (2) | O3—N1 | 1.198 (2) |
N2—H2A | 0.8900 | O4—N1 | 1.207 (2) |
N2—H2B | 0.8900 | N1—C2 | 1.455 (2) |
N2—H2C | 0.8902 | C1—C6 | 1.378 (3) |
C8—C9 | 1.377 (3) | C1—C2 | 1.382 (3) |
C8—C13 | 1.386 (3) | C1—C7 | 1.496 (3) |
C8—C8i | 1.477 (4) | C2—C3 | 1.357 (3) |
C9—C10 | 1.365 (3) | C3—C4 | 1.370 (3) |
C9—H9 | 0.9300 | C3—H3 | 0.9300 |
C10—C11 | 1.363 (3) | C4—C5 | 1.365 (3) |
C10—H10 | 0.9300 | C4—H4 | 0.9300 |
C11—C12 | 1.349 (3) | C5—C6 | 1.365 (3) |
C12—C13 | 1.374 (3) | C5—H5 | 0.9300 |
C12—H12 | 0.9300 | C6—H6 | 0.9300 |
C13—H13 | 0.9300 | O5—H5A | 0.819 (10) |
O1—C7 | 1.245 (2) | O5—H5B | 0.825 (10) |
O2—C7 | 1.247 (2) | ||
C11—N2—H2A | 109.7 | O3—N1—C2 | 118.44 (17) |
C11—N2—H2B | 109.1 | O4—N1—C2 | 119.08 (18) |
H2A—N2—H2B | 109.5 | C6—C1—C2 | 116.92 (18) |
C11—N2—H2C | 109.6 | C6—C1—C7 | 117.24 (17) |
H2A—N2—H2C | 109.5 | C2—C1—C7 | 125.84 (17) |
H2B—N2—H2C | 109.5 | C3—C2—C1 | 122.73 (18) |
C9—C8—C13 | 116.70 (19) | C3—C2—N1 | 117.55 (18) |
C9—C8—C8i | 121.8 (2) | C1—C2—N1 | 119.72 (17) |
C13—C8—C8i | 121.5 (2) | C2—C3—C4 | 118.96 (19) |
C10—C9—C8 | 121.8 (2) | C2—C3—H3 | 120.5 |
C10—C9—H9 | 119.1 | C4—C3—H3 | 120.5 |
C8—C9—H9 | 119.1 | C5—C4—C3 | 119.88 (19) |
C11—C10—C9 | 119.75 (19) | C5—C4—H4 | 120.1 |
C11—C10—H10 | 120.1 | C3—C4—H4 | 120.1 |
C9—C10—H10 | 120.1 | C4—C5—C6 | 120.53 (19) |
C12—C11—C10 | 120.59 (18) | C4—C5—H5 | 119.7 |
C12—C11—N2 | 119.94 (17) | C6—C5—H5 | 119.7 |
C10—C11—N2 | 119.47 (17) | C5—C6—C1 | 120.97 (19) |
C11—C12—C13 | 119.47 (19) | C5—C6—H6 | 119.5 |
C11—C12—H12 | 120.3 | C1—C6—H6 | 119.5 |
C13—C12—H12 | 120.3 | O1—C7—O2 | 125.68 (19) |
C12—C13—C8 | 121.70 (19) | O1—C7—C1 | 116.56 (18) |
C12—C13—H13 | 119.2 | O2—C7—C1 | 117.60 (18) |
C8—C13—H13 | 119.2 | H5A—O5—H5B | 109.5 (16) |
O3—N1—O4 | 122.47 (18) |
Symmetry code: (i) −x, y, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1ii | 0.89 | 1.86 | 2.744 (3) | 176 |
N2—H2B···O2 | 0.89 | 1.88 | 2.772 (3) | 176 |
N2—H2C···O5iii | 0.89 | 1.90 | 2.786 (2) | 178 |
O5—H5A···O2 | 0.82 (1) | 2.03 (1) | 2.852 (3) | 177 (3) |
O5—H5B···O1iv | 0.83 (1) | 1.98 (1) | 2.722 (3) | 149 (2) |
Symmetry codes: (ii) x, y+1, z; (iii) x, −y+1, z−1/2; (iv) −x+1/2, y+1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C12H14N22+·2C7H4NO4−·2H2O |
Mr | 554.51 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 298 |
a, b, c (Å) | 29.411 (10), 6.731 (6), 13.511 (6) |
β (°) | 110.91 (2) |
V (Å3) | 2499 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
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 | 0.983, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5946, 2185, 1386 |
Rint | 0.062 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.121, 0.96 |
No. of reflections | 2185 |
No. of parameters | 190 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.20, −0.20 |
Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), PLATON (Spek, 2003.
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1i | 0.89 | 1.86 | 2.744 (3) | 175.6 |
N2—H2B···O2 | 0.89 | 1.88 | 2.772 (3) | 175.5 |
N2—H2C···O5ii | 0.89 | 1.90 | 2.786 (2) | 178.4 |
O5—H5A···O2 | 0.819 (10) | 2.034 (10) | 2.852 (3) | 177 (3) |
O5—H5B···O1iii | 0.825 (10) | 1.980 (14) | 2.722 (3) | 149 (2) |
Symmetry codes: (i) x, y+1, z; (ii) x, −y+1, z−1/2; (iii) −x+1/2, y+1/2, −z+3/2. |
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This work continues our previous synthetic and structural studies of supramolecular salts (Wei, 2007). Herein we present the crystal structure of the title salt, (I).
The title salt contains one (1,1'-biphenyl)-4,4'-diammonium dication (with the complete molecule generated from the asymmetry atoms by 2-fold symmetry), one 2-nitrobenzoate anion and one crystallization water molecule (Fig. 1). Interestingly, these components are organized into an infinite two-dimensional network in (100) via intermolecular N—H···O and O—H···O hydrogen bonds (Table 1). Further hydrogen bonds link the planes into an infinite three-dimensional framework (Fig. 2).