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organic compounds
1,1′-Binaphthyl-2,2′-dicarboxylic acid–urea (1/1)
aInstitute of Bioorganic Chemistry, Academy of Sciences of Uzbekistan, H. Abdullaev Street 83, Tashkent 100125, Uzbekistan, and bInstitute für Organische Chemie, TU Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, Germany
*Correspondence e-mail: l_izotova@yahoo.com
In the title 22H14O4·CH4N2O, the 1,1′-binaphthyl-2,2′-dicarboxylic acid (BNDA) and urea molecules are connected via a system of hydrogen bonds into a chiral two-dimensional polymeric structure parallel to the (001) plane. As the crystal is centrosymmetric, it consists of alternately stacked BNDA–urea layers of opposite The urea H atoms trans to the C=O group are bonded in a chelating mode [R12(6)] to the carbonyl O atom from one of the carboxylic acid groups which, in turn, acts as the donor of an O—H⋯O hydrogen bond to another urea molecule. The [010] chains thus formed are further connected via an R22(8) hydrogen-bond motif formed between urea and the second carboxylic acid group of BNDA.
CRelated literature
For information on inclusion compounds of 1,1′-binaphthyl-2,2′-dicarboxylic acid, see: Weber (1996). For the synthesis of 1,1′-binaphthyl-2,2′-dicarboxylic acid, see: Weber et al. (1984
).
Experimental
Crystal data
|
Data collection
|
Refinement
|
|
Data collection: STADI4 (Stoe & Cie, 1997); cell STADI4; data reduction: X-RED (Stoe & Cie, 1997
); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: XP (Siemens, 1994
); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536808028997/gk2167sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808028997/gk2167Isup2.hkl
1,1'-Binaphthyl-2,2'-dicarboxylic acid was synthesized according to Weber et al. (1984). Slow evaporation of acetone/water solution of equimolar mixture of BNDA and urea resulted in colourless crystals stable in air and suitable for X-ray analysis.
H atoms from the OH and NH2 groups were located from difference Fourier maps and fully refined. The remaining H atoms were positioned geometrically (C—H 0.93 Å) and refined as riding on their carrier atoms with Uiso(H) = 1.2Ueq(C).
Data collection: STADI4 (Stoe & Cie, 1997); cell
STADI4 (Stoe & Cie, 1997); data reduction: X-RED (Stoe & Cie, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C22H14O4·CH4N2O | F(000) = 840 |
Mr = 402.39 | Dx = 1.368 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 9.2560 (19) Å | θ = 10–25° |
b = 12.033 (2) Å | µ = 0.10 mm−1 |
c = 17.958 (4) Å | T = 293 K |
β = 102.40 (3)° | Prism, colourless |
V = 1953.5 (7) Å3 | 0.21 × 0.17 × 0.12 mm |
Z = 4 |
Stoe STADI4 diffractometer | Rint = 0.000 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.8° |
Graphite monochromator | h = −11→10 |
ω/2θ scans | k = 0→14 |
3416 measured reflections | l = 0→21 |
3416 independent reflections | 3 standard reflections every 100 reflections |
2874 reflections with I > 2σ(I) | intensity decay: 2.1% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.117 | w = 1/[σ2(Fo2) + (0.050P)2 + 0.871P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
3416 reflections | Δρmax = 0.21 e Å−3 |
296 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0083 (11) |
C22H14O4·CH4N2O | V = 1953.5 (7) Å3 |
Mr = 402.39 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.2560 (19) Å | µ = 0.10 mm−1 |
b = 12.033 (2) Å | T = 293 K |
c = 17.958 (4) Å | 0.21 × 0.17 × 0.12 mm |
β = 102.40 (3)° |
Stoe STADI4 diffractometer | Rint = 0.000 |
3416 measured reflections | 3 standard reflections every 100 reflections |
3416 independent reflections | intensity decay: 2.1% |
2874 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.117 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | Δρmax = 0.21 e Å−3 |
3416 reflections | Δρmin = −0.18 e Å−3 |
296 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 | ||
O1 | 1.04973 (17) | 0.78156 (13) | 0.14183 (10) | 0.0668 (5) | |
O2 | 1.08667 (16) | 0.61883 (12) | 0.19956 (9) | 0.0529 (4) | |
O3 | 0.6667 (2) | 1.06357 (13) | 0.10984 (10) | 0.0687 (5) | |
O4 | 0.6785 (2) | 0.89894 (13) | 0.16344 (10) | 0.0718 (5) | |
C1 | 0.74291 (19) | 0.71568 (14) | 0.08151 (10) | 0.0335 (4) | |
C2 | 0.84438 (19) | 0.65851 (14) | 0.13592 (10) | 0.0351 (4) | |
C3 | 0.7992 (2) | 0.56422 (15) | 0.17243 (11) | 0.0407 (4) | |
H3A | 0.8687 | 0.5252 | 0.2080 | 0.049* | |
C4 | 0.6563 (2) | 0.52994 (16) | 0.15642 (11) | 0.0450 (5) | |
H4A | 0.6288 | 0.4687 | 0.1818 | 0.054* | |
C5 | 0.3993 (2) | 0.55259 (17) | 0.08479 (13) | 0.0531 (5) | |
H5A | 0.3696 | 0.4931 | 0.1109 | 0.064* | |
C6 | 0.2983 (2) | 0.60591 (18) | 0.03102 (15) | 0.0587 (6) | |
H6A | 0.1999 | 0.5835 | 0.0211 | 0.070* | |
C7 | 0.3414 (2) | 0.69477 (17) | −0.00973 (14) | 0.0544 (6) | |
H7A | 0.2720 | 0.7297 | −0.0476 | 0.065* | |
C8 | 0.4844 (2) | 0.73021 (16) | 0.00577 (12) | 0.0448 (5) | |
H8A | 0.5112 | 0.7896 | −0.0215 | 0.054* | |
C9 | 0.5929 (2) | 0.67850 (14) | 0.06262 (10) | 0.0364 (4) | |
C10 | 0.5492 (2) | 0.58588 (15) | 0.10188 (11) | 0.0403 (4) | |
C11 | 0.78527 (18) | 0.80838 (14) | 0.03449 (10) | 0.0333 (4) | |
C12 | 0.75590 (19) | 0.91925 (15) | 0.04525 (10) | 0.0364 (4) | |
C13 | 0.7863 (2) | 1.00037 (15) | −0.00665 (11) | 0.0439 (5) | |
H13A | 0.7633 | 1.0744 | 0.0001 | 0.053* | |
C14 | 0.8480 (2) | 0.97206 (16) | −0.06573 (12) | 0.0465 (5) | |
H14A | 0.8681 | 1.0270 | −0.0985 | 0.056* | |
C15 | 0.9495 (2) | 0.82851 (19) | −0.13856 (11) | 0.0491 (5) | |
H15A | 0.9765 | 0.8828 | −0.1698 | 0.059* | |
C16 | 0.9756 (2) | 0.7203 (2) | −0.15173 (12) | 0.0546 (6) | |
H16A | 1.0196 | 0.7010 | −0.1918 | 0.065* | |
C17 | 0.9363 (2) | 0.63771 (19) | −0.10509 (12) | 0.0521 (5) | |
H17A | 0.9518 | 0.5634 | −0.1152 | 0.062* | |
C18 | 0.8756 (2) | 0.66547 (16) | −0.04486 (11) | 0.0423 (5) | |
H18A | 0.8524 | 0.6096 | −0.0136 | 0.051* | |
C19 | 0.84714 (18) | 0.77740 (15) | −0.02885 (10) | 0.0342 (4) | |
C20 | 0.88207 (19) | 0.86064 (16) | −0.07834 (10) | 0.0381 (4) | |
C21 | 1.0017 (2) | 0.69403 (15) | 0.15798 (10) | 0.0385 (4) | |
C22 | 0.6974 (2) | 0.95702 (15) | 0.11195 (11) | 0.0408 (4) | |
C23 | 0.4379 (2) | 0.74181 (17) | 0.24467 (11) | 0.0435 (5) | |
N1 | 0.3833 (2) | 0.81441 (17) | 0.18972 (12) | 0.0572 (5) | |
N2 | 0.5812 (2) | 0.7509 (2) | 0.27794 (14) | 0.0690 (6) | |
O5 | 0.35758 (16) | 0.67037 (14) | 0.26518 (9) | 0.0594 (4) | |
H1N | 0.445 (3) | 0.857 (2) | 0.1710 (13) | 0.063 (7)* | |
H2N | 0.280 (3) | 0.807 (2) | 0.1663 (16) | 0.087 (9)* | |
H2 | 1.189 (3) | 0.650 (2) | 0.2168 (15) | 0.083 (8)* | |
H3 | 0.641 (3) | 1.091 (3) | 0.1565 (18) | 0.100 (10)* | |
H3N | 0.633 (3) | 0.795 (2) | 0.2542 (17) | 0.083 (9)* | |
H4N | 0.615 (3) | 0.700 (3) | 0.3100 (19) | 0.093 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0498 (9) | 0.0573 (10) | 0.0848 (12) | −0.0176 (7) | −0.0043 (8) | 0.0312 (9) |
O2 | 0.0416 (8) | 0.0458 (8) | 0.0690 (10) | −0.0008 (6) | 0.0066 (7) | 0.0127 (7) |
O3 | 0.1151 (15) | 0.0404 (9) | 0.0566 (10) | 0.0209 (9) | 0.0317 (10) | −0.0009 (7) |
O4 | 0.1210 (15) | 0.0406 (8) | 0.0708 (11) | −0.0034 (9) | 0.0585 (11) | 0.0006 (8) |
C1 | 0.0404 (10) | 0.0274 (9) | 0.0344 (9) | −0.0037 (7) | 0.0121 (7) | −0.0020 (7) |
C2 | 0.0403 (10) | 0.0317 (9) | 0.0350 (9) | −0.0020 (7) | 0.0120 (7) | −0.0011 (7) |
C3 | 0.0473 (11) | 0.0363 (10) | 0.0384 (10) | −0.0021 (8) | 0.0091 (8) | 0.0055 (8) |
C4 | 0.0519 (12) | 0.0359 (10) | 0.0491 (11) | −0.0097 (9) | 0.0153 (9) | 0.0079 (8) |
C5 | 0.0490 (12) | 0.0401 (11) | 0.0712 (14) | −0.0126 (9) | 0.0153 (11) | 0.0033 (10) |
C6 | 0.0412 (11) | 0.0461 (12) | 0.0859 (17) | −0.0108 (10) | 0.0073 (11) | −0.0033 (12) |
C7 | 0.0447 (11) | 0.0411 (11) | 0.0705 (14) | −0.0001 (9) | −0.0028 (10) | −0.0010 (10) |
C8 | 0.0447 (11) | 0.0336 (10) | 0.0539 (12) | −0.0021 (8) | 0.0058 (9) | 0.0017 (9) |
C9 | 0.0404 (10) | 0.0294 (9) | 0.0411 (10) | −0.0028 (7) | 0.0126 (8) | −0.0027 (7) |
C10 | 0.0424 (10) | 0.0326 (9) | 0.0484 (11) | −0.0067 (8) | 0.0149 (8) | −0.0020 (8) |
C11 | 0.0344 (9) | 0.0306 (9) | 0.0346 (9) | −0.0048 (7) | 0.0069 (7) | 0.0010 (7) |
C12 | 0.0387 (10) | 0.0311 (9) | 0.0395 (10) | −0.0030 (8) | 0.0086 (8) | −0.0004 (7) |
C13 | 0.0524 (11) | 0.0293 (9) | 0.0511 (12) | −0.0001 (8) | 0.0134 (9) | 0.0049 (8) |
C14 | 0.0566 (12) | 0.0386 (11) | 0.0460 (11) | −0.0028 (9) | 0.0150 (9) | 0.0139 (9) |
C15 | 0.0494 (12) | 0.0611 (13) | 0.0392 (10) | −0.0014 (10) | 0.0151 (9) | 0.0077 (9) |
C16 | 0.0555 (13) | 0.0698 (15) | 0.0427 (11) | 0.0060 (11) | 0.0199 (10) | −0.0055 (11) |
C17 | 0.0571 (13) | 0.0484 (12) | 0.0536 (12) | 0.0049 (10) | 0.0181 (10) | −0.0100 (10) |
C18 | 0.0471 (11) | 0.0360 (10) | 0.0453 (11) | −0.0026 (8) | 0.0130 (9) | −0.0021 (8) |
C19 | 0.0328 (9) | 0.0343 (9) | 0.0346 (9) | −0.0029 (7) | 0.0050 (7) | −0.0006 (7) |
C20 | 0.0367 (9) | 0.0435 (10) | 0.0334 (9) | −0.0024 (8) | 0.0061 (7) | 0.0043 (8) |
C21 | 0.0421 (10) | 0.0381 (10) | 0.0362 (9) | −0.0038 (8) | 0.0100 (8) | 0.0022 (8) |
C22 | 0.0442 (10) | 0.0318 (10) | 0.0473 (11) | −0.0023 (8) | 0.0117 (9) | −0.0026 (8) |
C23 | 0.0412 (10) | 0.0495 (12) | 0.0415 (10) | −0.0041 (9) | 0.0124 (8) | 0.0005 (9) |
N1 | 0.0524 (12) | 0.0565 (12) | 0.0638 (12) | −0.0064 (9) | 0.0149 (10) | 0.0165 (10) |
N2 | 0.0466 (11) | 0.0865 (17) | 0.0713 (14) | −0.0114 (11) | 0.0071 (10) | 0.0190 (13) |
O5 | 0.0469 (8) | 0.0691 (10) | 0.0601 (9) | −0.0124 (7) | 0.0067 (7) | 0.0239 (8) |
O1—C21 | 1.203 (2) | C11—C12 | 1.383 (2) |
O2—C21 | 1.320 (2) | C11—C19 | 1.428 (2) |
O2—H2 | 1.00 (3) | C12—C13 | 1.419 (3) |
O3—C22 | 1.312 (2) | C12—C22 | 1.487 (3) |
O3—H3 | 0.98 (3) | C13—C14 | 1.352 (3) |
O4—C22 | 1.202 (2) | C13—H13A | 0.9300 |
C1—C2 | 1.384 (3) | C14—C20 | 1.407 (3) |
C1—C9 | 1.429 (3) | C14—H14A | 0.9300 |
C1—C11 | 1.501 (2) | C15—C16 | 1.354 (3) |
C2—C3 | 1.418 (2) | C15—C20 | 1.413 (3) |
C2—C21 | 1.488 (3) | C15—H15A | 0.9300 |
C3—C4 | 1.356 (3) | C16—C17 | 1.397 (3) |
C3—H3A | 0.9300 | C16—H16A | 0.9300 |
C4—C10 | 1.406 (3) | C17—C18 | 1.364 (3) |
C4—H4A | 0.9300 | C17—H17A | 0.9300 |
C5—C6 | 1.353 (3) | C18—C19 | 1.414 (3) |
C5—C10 | 1.414 (3) | C18—H18A | 0.9300 |
C5—H5A | 0.9300 | C19—C20 | 1.422 (2) |
C6—C7 | 1.401 (3) | C23—O5 | 1.243 (2) |
C6—H6A | 0.9300 | C23—N1 | 1.334 (3) |
C7—C8 | 1.361 (3) | C23—N2 | 1.337 (3) |
C7—H7A | 0.9300 | N1—H1N | 0.89 (3) |
C8—C9 | 1.413 (3) | N1—H2N | 0.96 (3) |
C8—H8A | 0.9300 | N2—H3N | 0.88 (3) |
C9—C10 | 1.423 (3) | N2—H4N | 0.85 (3) |
C21—O2—H2 | 109.1 (16) | C14—C13—H13A | 119.4 |
C22—O3—H3 | 113.5 (18) | C12—C13—H13A | 119.4 |
C2—C1—C9 | 119.32 (16) | C13—C14—C20 | 120.91 (17) |
C2—C1—C11 | 123.14 (16) | C13—C14—H14A | 119.5 |
C9—C1—C11 | 117.20 (15) | C20—C14—H14A | 119.5 |
C1—C2—C3 | 120.09 (16) | C16—C15—C20 | 121.41 (19) |
C1—C2—C21 | 121.49 (16) | C16—C15—H15A | 119.3 |
C3—C2—C21 | 118.42 (16) | C20—C15—H15A | 119.3 |
C4—C3—C2 | 121.10 (18) | C15—C16—C17 | 120.02 (19) |
C4—C3—H3A | 119.5 | C15—C16—H16A | 120.0 |
C2—C3—H3A | 119.5 | C17—C16—H16A | 120.0 |
C3—C4—C10 | 120.76 (17) | C18—C17—C16 | 120.4 (2) |
C3—C4—H4A | 119.6 | C18—C17—H17A | 119.8 |
C10—C4—H4A | 119.6 | C16—C17—H17A | 119.8 |
C6—C5—C10 | 121.1 (2) | C17—C18—C19 | 121.42 (19) |
C6—C5—H5A | 119.5 | C17—C18—H18A | 119.3 |
C10—C5—H5A | 119.5 | C19—C18—H18A | 119.3 |
C5—C6—C7 | 120.3 (2) | C18—C19—C20 | 117.83 (16) |
C5—C6—H6A | 119.9 | C18—C19—C11 | 122.32 (16) |
C7—C6—H6A | 119.9 | C20—C19—C11 | 119.85 (16) |
C8—C7—C6 | 120.4 (2) | C14—C20—C15 | 122.35 (18) |
C8—C7—H7A | 119.8 | C14—C20—C19 | 118.80 (17) |
C6—C7—H7A | 119.8 | C15—C20—C19 | 118.86 (18) |
C7—C8—C9 | 121.25 (19) | O1—C21—O2 | 122.05 (18) |
C7—C8—H8A | 119.4 | O1—C21—C2 | 125.36 (17) |
C9—C8—H8A | 119.4 | O2—C21—C2 | 112.58 (16) |
C8—C9—C10 | 117.99 (17) | O4—C22—O3 | 121.59 (19) |
C8—C9—C1 | 122.51 (16) | O4—C22—C12 | 125.48 (17) |
C10—C9—C1 | 119.51 (17) | O3—C22—C12 | 112.93 (17) |
C4—C10—C5 | 121.86 (18) | O5—C23—N1 | 121.08 (19) |
C4—C10—C9 | 119.16 (17) | O5—C23—N2 | 121.6 (2) |
C5—C10—C9 | 118.98 (18) | N1—C23—N2 | 117.3 (2) |
C12—C11—C19 | 119.17 (16) | C23—N1—H1N | 118.9 (16) |
C12—C11—C1 | 123.72 (16) | C23—N1—H2N | 116.6 (17) |
C19—C11—C1 | 116.86 (15) | H1N—N1—H2N | 123 (2) |
C11—C12—C13 | 119.94 (17) | C23—N2—H3N | 115.2 (19) |
C11—C12—C22 | 121.57 (16) | C23—N2—H4N | 115 (2) |
C13—C12—C22 | 118.46 (16) | H3N—N2—H4N | 127 (3) |
C14—C13—C12 | 121.26 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O4 | 0.89 (3) | 2.25 (3) | 3.046 (3) | 149 (2) |
N1—H2N···O1i | 0.96 (3) | 2.10 (3) | 3.048 (3) | 166 (2) |
O2—H2···O5ii | 1.00 (3) | 1.63 (3) | 2.606 (2) | 162 (2) |
O3—H3···O5iii | 0.98 (3) | 1.70 (3) | 2.637 (2) | 160 (3) |
N2—H3N···O4 | 0.88 (3) | 2.17 (3) | 3.001 (3) | 157 (3) |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x+1, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C22H14O4·CH4N2O |
Mr | 402.39 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 9.2560 (19), 12.033 (2), 17.958 (4) |
β (°) | 102.40 (3) |
V (Å3) | 1953.5 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.21 × 0.17 × 0.12 |
Data collection | |
Diffractometer | Stoe STADI4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3416, 3416, 2874 |
Rint | 0.000 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.117, 1.09 |
No. of reflections | 3416 |
No. of parameters | 296 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.21, −0.18 |
Computer programs: STADI4 (Stoe & Cie, 1997), X-RED (Stoe & Cie, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Siemens, 1994).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O4 | 0.89 (3) | 2.25 (3) | 3.046 (3) | 149 (2) |
N1—H2N···O1i | 0.96 (3) | 2.10 (3) | 3.048 (3) | 166 (2) |
O2—H2···O5ii | 1.00 (3) | 1.63 (3) | 2.606 (2) | 162 (2) |
O3—H3···O5iii | 0.98 (3) | 1.70 (3) | 2.637 (2) | 160 (3) |
N2—H3N···O4 | 0.88 (3) | 2.17 (3) | 3.001 (3) | 157 (3) |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x+1, y+1/2, −z+1/2. |
Acknowledgements
Support of this research by the Uzbek Academy of Sciences (grant No. FA-F3-T141) is gratefully acknowledged.
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Crystal engineering involves design and synthesis of solid-state structures with desired properties, based on an understanding and exploitation of intermolecular interactions. 1,1'-Binaphthyl-2,2'-dicarboxylic acid (BNDA) (Weber, 1996) and urea are well known supramolecular substrates forming a large variety of multicomponent crystals. To study supramolecular interactions in the BNDA–urea system co-crystals were prepared and their structure determined by X-ray structure analysis. The two compounds co-crystallize in a 1:1 molar ratio with molecules located in general position (Fig. 1). The BNDA adopts its usual conformation with the two naphthyl units nearly perpendicular [dihedral angle of 79.77 (5)°].
In the crystal structure, the urea molecule is involved in five hydrogen bonds - twice as an acceptor and three times as a donor (Table 1). One of the cis hydrogen atoms does not take part in conventional hydrogen bonding but is involved in a weak interaction with the π system of one of the naphthalene units. The carboxylic group O1,C21,O2 is bonded to the urea molecule via the cyclic R22(8) motif. The other BNDA carboxylic group acts also as a donor to the urea carbonyl, however its O4 atom accepts two N—H···O hydrogen bonds which are a part of the R12(6) motif (Fig. 2). The hydrogen bonds between urea and BNDA assemble molecules into layers parallel to (001). The hydrogen-bonded BNDA–urea layers are chiral and consist of homochiral BNDA molecules. However, the crystal is centrosymmetric and thus it is built from alternate stacks of layers of opposite chirality.