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The title molecule, C
12H
13NO
3, is a pentacycloundecane cage derivative that exhibits C—C bond lengths deviating from the normal values. Neighbouring molecules interact
via N—H
O and O—H
O hydrogen bonds, forming two-dimensional hydrogen-bonded sheets.
Supporting information
CCDC reference: 296578
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C)= 0.002 Å
- R factor = 0.039
- wR factor = 0.107
- Data-to-parameter ratio = 15.0
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
The PCU lactam was synthesized as described by Martins et al. (1993) and recrystalized from dioxane.
Atoms H1H, H2H and H3H were located in a difference map and refined isotropically [N—H = 0.924 (17) Å and O—H = 0.83 (2) and 0.89 (2) Å]. The remaining H atoms were positioned geometrically [C—H = 1.00 (CH) and 0.99 Å (CH2)] and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C).
Data collection: SMART-NT (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Mercury (Bruno et al., 2002) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).
8,11-Dihydroxypentacycloundecane-8,11-lactam
top
Crystal data top
C12H13NO3 | F(000) = 928 |
Mr = 219.23 | Dx = 1.543 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 957 reflections |
a = 22.0040 (11) Å | θ = 3.0–28.3° |
b = 6.3299 (3) Å | µ = 0.11 mm−1 |
c = 13.6153 (7) Å | T = 173 K |
β = 95.426 (3)° | Block, colourless |
V = 1887.88 (16) Å3 | 0.38 × 0.29 × 0.29 mm |
Z = 8 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 1973 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.043 |
Graphite monochromator | θmax = 28.3°, θmin = 1.9° |
ϕ and ω scans | h = −26→29 |
7588 measured reflections | k = −7→8 |
2354 independent reflections | l = −18→18 |
Refinement top
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0585P)2 + 0.9852P] where P = (Fo2 + 2Fc2)/3 |
2354 reflections | (Δ/σ)max < 0.001 |
157 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
Crystal data top
C12H13NO3 | V = 1887.88 (16) Å3 |
Mr = 219.23 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 22.0040 (11) Å | µ = 0.11 mm−1 |
b = 6.3299 (3) Å | T = 173 K |
c = 13.6153 (7) Å | 0.38 × 0.29 × 0.29 mm |
β = 95.426 (3)° | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 1973 reflections with I > 2σ(I) |
7588 measured reflections | Rint = 0.043 |
2354 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.107 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.38 e Å−3 |
2354 reflections | Δρmin = −0.21 e Å−3 |
157 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N | 0.43856 (5) | 0.30382 (17) | −0.00885 (7) | 0.0169 (2) | |
O1 | 0.48796 (4) | 0.44217 (14) | −0.13557 (6) | 0.0197 (2) | |
O2 | 0.42018 (5) | 0.20134 (16) | −0.27049 (6) | 0.0226 (2) | |
O3 | 0.38821 (4) | 0.15590 (16) | 0.11695 (6) | 0.0219 (2) | |
C1 | 0.41021 (5) | −0.07299 (19) | −0.02310 (8) | 0.0172 (2) | |
C2 | 0.34818 (6) | −0.1881 (2) | −0.04946 (9) | 0.0194 (3) | |
C3 | 0.29673 (5) | −0.0259 (2) | −0.03722 (8) | 0.0184 (3) | |
C4 | 0.25715 (6) | −0.0377 (2) | −0.13638 (9) | 0.0228 (3) | |
C5 | 0.31036 (6) | −0.0020 (2) | −0.19988 (8) | 0.0187 (3) | |
C6 | 0.35769 (6) | −0.1703 (2) | −0.16228 (8) | 0.0192 (3) | |
C7 | 0.41998 (5) | −0.05508 (19) | −0.13520 (8) | 0.0174 (2) | |
C8 | 0.40947 (5) | 0.17571 (19) | −0.16976 (8) | 0.0159 (2) | |
C9 | 0.34104 (5) | 0.20274 (19) | −0.15607 (8) | 0.0156 (2) | |
C10 | 0.33154 (5) | 0.18463 (19) | −0.04339 (8) | 0.0155 (2) | |
C11 | 0.39365 (5) | 0.14539 (19) | 0.01531 (8) | 0.0155 (2) | |
C12 | 0.44940 (5) | 0.32326 (18) | −0.10356 (8) | 0.0156 (2) | |
H1 | 0.4419 | −0.1538 | 0.0189 | 0.021* | |
H1H | 0.4618 (7) | 0.377 (3) | 0.0400 (12) | 0.023 (4)* | |
H2H | 0.4456 (9) | 0.296 (3) | −0.2752 (14) | 0.039 (5)* | |
H2 | 0.3434 | −0.3328 | −0.0217 | 0.023* | |
H3 | 0.2744 | −0.0444 | 0.0228 | 0.022* | |
H3H | 0.4041 (10) | 0.041 (4) | 0.1458 (15) | 0.053 (6)* | |
H4A | 0.2375 | −0.1773 | −0.1480 | 0.027* | |
H4B | 0.2262 | 0.0759 | −0.1442 | 0.027* | |
H5 | 0.2992 | −0.0005 | −0.2728 | 0.022* | |
H6 | 0.3586 | −0.3048 | −0.2007 | 0.023* | |
H7 | 0.4571 | −0.1265 | −0.1565 | 0.021* | |
H9 | 0.3231 | 0.3344 | −0.1873 | 0.019* | |
H10 | 0.3091 | 0.3079 | −0.0183 | 0.019* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N | 0.0183 (5) | 0.0205 (5) | 0.0115 (4) | −0.0037 (4) | −0.0002 (4) | −0.0018 (4) |
O1 | 0.0213 (4) | 0.0221 (5) | 0.0160 (4) | −0.0064 (4) | 0.0032 (3) | −0.0011 (3) |
O2 | 0.0293 (5) | 0.0279 (5) | 0.0111 (4) | −0.0112 (4) | 0.0040 (3) | −0.0021 (3) |
O3 | 0.0289 (5) | 0.0264 (5) | 0.0109 (4) | 0.0004 (4) | 0.0035 (3) | 0.0018 (3) |
C1 | 0.0182 (6) | 0.0172 (6) | 0.0161 (5) | 0.0029 (4) | 0.0004 (4) | 0.0030 (4) |
C2 | 0.0228 (6) | 0.0151 (6) | 0.0202 (5) | −0.0013 (5) | 0.0019 (4) | 0.0029 (4) |
C3 | 0.0175 (6) | 0.0204 (6) | 0.0175 (5) | −0.0027 (5) | 0.0027 (4) | 0.0007 (4) |
C4 | 0.0192 (6) | 0.0266 (7) | 0.0221 (6) | −0.0054 (5) | 0.0001 (5) | 0.0006 (5) |
C5 | 0.0204 (6) | 0.0192 (6) | 0.0159 (5) | −0.0041 (5) | −0.0019 (4) | −0.0009 (4) |
C6 | 0.0240 (6) | 0.0154 (6) | 0.0184 (5) | −0.0027 (5) | 0.0029 (4) | −0.0023 (4) |
C7 | 0.0186 (6) | 0.0168 (6) | 0.0169 (5) | 0.0011 (4) | 0.0025 (4) | −0.0015 (4) |
C8 | 0.0191 (6) | 0.0182 (6) | 0.0106 (5) | −0.0029 (4) | 0.0019 (4) | −0.0006 (4) |
C9 | 0.0165 (5) | 0.0160 (6) | 0.0139 (5) | −0.0004 (4) | −0.0012 (4) | 0.0019 (4) |
C10 | 0.0159 (5) | 0.0162 (6) | 0.0145 (5) | 0.0015 (4) | 0.0018 (4) | 0.0010 (4) |
C11 | 0.0172 (5) | 0.0183 (6) | 0.0111 (5) | −0.0003 (4) | 0.0020 (4) | 0.0008 (4) |
C12 | 0.0159 (5) | 0.0163 (6) | 0.0142 (5) | 0.0007 (4) | 0.0003 (4) | −0.0008 (4) |
Geometric parameters (Å, º) top
C12—O1 | 1.2435 (14) | C9—H9 | 1.0000 |
C12—N | 1.3389 (14) | C5—C4 | 1.5365 (17) |
C12—C8 | 1.5189 (16) | C5—C6 | 1.5430 (18) |
C8—O2 | 1.4226 (12) | C5—H5 | 1.0000 |
C8—C9 | 1.5442 (16) | C6—C2 | 1.5738 (16) |
C8—C7 | 1.5455 (17) | C6—H6 | 1.0000 |
C7—C1 | 1.5654 (15) | C2—C3 | 1.5489 (17) |
C7—C6 | 1.5655 (17) | C2—H2 | 1.0000 |
C7—H7 | 1.0000 | C3—C4 | 1.5376 (17) |
C1—C11 | 1.5341 (17) | C3—C10 | 1.5431 (16) |
C1—C2 | 1.5588 (17) | C3—H3 | 1.0000 |
C1—H1 | 1.0000 | C10—H10 | 1.0000 |
C11—O3 | 1.4019 (13) | C4—H4A | 0.9900 |
C11—N | 1.4670 (15) | C4—H4B | 0.9900 |
C11—C10 | 1.5368 (16) | N—H1H | 0.924 (17) |
C9—C5 | 1.5539 (16) | O2—H2H | 0.83 (2) |
C9—C10 | 1.5719 (15) | O3—H3H | 0.89 (2) |
| | | |
O1—C12—N | 125.64 (11) | C6—C5—H5 | 115.5 |
O1—C12—C8 | 122.67 (10) | C9—C5—H5 | 115.5 |
N—C12—C8 | 111.67 (10) | C5—C6—C7 | 107.76 (10) |
O2—C8—C12 | 111.27 (9) | C5—C6—C2 | 103.03 (9) |
O2—C8—C9 | 110.85 (9) | C7—C6—C2 | 89.86 (9) |
C12—C8—C9 | 112.09 (9) | C5—C6—H6 | 117.4 |
O2—C8—C7 | 111.58 (9) | C7—C6—H6 | 117.4 |
C12—C8—C7 | 109.82 (9) | C2—C6—H6 | 117.4 |
C9—C8—C7 | 100.81 (9) | C3—C2—C1 | 107.37 (10) |
C8—C7—C1 | 109.57 (9) | C3—C2—C6 | 102.92 (9) |
C8—C7—C6 | 105.43 (9) | C1—C2—C6 | 89.82 (9) |
C1—C7—C6 | 89.89 (8) | C3—C2—H2 | 117.5 |
C8—C7—H7 | 116.2 | C1—C2—H2 | 117.5 |
C1—C7—H7 | 116.2 | C6—C2—H2 | 117.5 |
C6—C7—H7 | 116.2 | C4—C3—C10 | 103.71 (10) |
C11—C1—C2 | 105.57 (9) | C4—C3—C2 | 103.44 (10) |
C11—C1—C7 | 109.03 (9) | C10—C3—C2 | 101.24 (9) |
C2—C1—C7 | 90.42 (8) | C4—C3—H3 | 115.5 |
C11—C1—H1 | 116.2 | C10—C3—H3 | 115.5 |
C2—C1—H1 | 116.2 | C2—C3—H3 | 115.5 |
C7—C1—H1 | 116.2 | C11—C10—C3 | 104.70 (9) |
O3—C11—N | 108.13 (9) | C11—C10—C9 | 109.00 (9) |
O3—C11—C1 | 115.12 (9) | C3—C10—C9 | 103.22 (9) |
N—C11—C1 | 110.65 (9) | C11—C10—H10 | 113.1 |
O3—C11—C10 | 110.55 (9) | C3—C10—H10 | 113.1 |
N—C11—C10 | 110.96 (9) | C9—C10—H10 | 113.1 |
C1—C11—C10 | 101.34 (9) | C5—C4—C3 | 95.08 (9) |
C8—C9—C5 | 104.74 (9) | C5—C4—H4A | 112.7 |
C8—C9—C10 | 109.33 (9) | C3—C4—H4A | 112.7 |
C5—C9—C10 | 102.75 (9) | C5—C4—H4B | 112.7 |
C8—C9—H9 | 113.1 | C3—C4—H4B | 112.7 |
C5—C9—H9 | 113.1 | H4A—C4—H4B | 110.2 |
C10—C9—H9 | 113.1 | C12—N—C11 | 117.64 (9) |
C4—C5—C6 | 103.77 (10) | C12—N—H1H | 120.7 (10) |
C4—C5—C9 | 103.49 (10) | C11—N—H1H | 121.3 (10) |
C6—C5—C9 | 101.14 (9) | C8—O2—H2H | 109.4 (13) |
C4—C5—H5 | 115.5 | C11—O3—H3H | 109.3 (13) |
| | | |
O1—C12—C8—O2 | −2.99 (16) | C8—C7—C6—C2 | −110.38 (9) |
N—C12—C8—O2 | 178.49 (10) | C1—C7—C6—C2 | −0.07 (9) |
O1—C12—C8—C9 | −127.76 (11) | C11—C1—C2—C3 | 6.35 (11) |
N—C12—C8—C9 | 53.72 (13) | C7—C1—C2—C3 | −103.56 (9) |
O1—C12—C8—C7 | 121.05 (12) | C11—C1—C2—C6 | 109.84 (9) |
N—C12—C8—C7 | −57.46 (13) | C7—C1—C2—C6 | −0.07 (9) |
O2—C8—C7—C1 | 177.74 (9) | C5—C6—C2—C3 | −0.34 (11) |
C12—C8—C7—C1 | 53.87 (12) | C7—C6—C2—C3 | 107.87 (10) |
C9—C8—C7—C1 | −64.54 (11) | C5—C6—C2—C1 | −108.14 (10) |
O2—C8—C7—C6 | −86.75 (11) | C7—C6—C2—C1 | 0.07 (9) |
C12—C8—C7—C6 | 149.38 (9) | C1—C2—C3—C4 | 127.60 (10) |
C9—C8—C7—C6 | 30.97 (10) | C6—C2—C3—C4 | 33.68 (11) |
C8—C7—C1—C11 | −0.21 (13) | C1—C2—C3—C10 | 20.39 (11) |
C6—C7—C1—C11 | −106.58 (10) | C6—C2—C3—C10 | −73.54 (10) |
C8—C7—C1—C2 | 106.44 (10) | O3—C11—C10—C3 | −77.83 (11) |
C6—C7—C1—C2 | 0.07 (9) | N—C11—C10—C3 | 162.21 (9) |
C2—C1—C11—O3 | 88.74 (11) | C1—C11—C10—C3 | 44.69 (10) |
C7—C1—C11—O3 | −175.28 (9) | O3—C11—C10—C9 | 172.28 (9) |
C2—C1—C11—N | −148.30 (9) | N—C11—C10—C9 | 52.31 (12) |
C7—C1—C11—N | −52.32 (12) | C1—C11—C10—C9 | −65.20 (11) |
C2—C1—C11—C10 | −30.56 (10) | C4—C3—C10—C11 | −147.28 (10) |
C7—C1—C11—C10 | 65.42 (11) | C2—C3—C10—C11 | −40.28 (11) |
O2—C8—C9—C5 | 73.28 (11) | C4—C3—C10—C9 | −33.25 (11) |
C12—C8—C9—C5 | −161.72 (9) | C2—C3—C10—C9 | 73.75 (10) |
C7—C8—C9—C5 | −44.98 (10) | C8—C9—C10—C11 | −0.16 (13) |
O2—C8—C9—C10 | −177.20 (9) | C5—C9—C10—C11 | 110.69 (10) |
C12—C8—C9—C10 | −52.19 (12) | C8—C9—C10—C3 | −111.04 (10) |
C7—C8—C9—C10 | 64.55 (10) | C5—C9—C10—C3 | −0.19 (11) |
C8—C9—C5—C4 | 147.81 (9) | C6—C5—C4—C3 | 52.63 (11) |
C10—C9—C5—C4 | 33.57 (11) | C9—C5—C4—C3 | −52.64 (11) |
C8—C9—C5—C6 | 40.56 (10) | C10—C3—C4—C5 | 52.64 (11) |
C10—C9—C5—C6 | −73.68 (10) | C2—C3—C4—C5 | −52.70 (11) |
C4—C5—C6—C7 | −127.27 (10) | O1—C12—N—C11 | −176.38 (11) |
C9—C5—C6—C7 | −20.23 (11) | C8—C12—N—C11 | 2.08 (15) |
C4—C5—C6—C2 | −33.17 (11) | O3—C11—N—C12 | −178.36 (10) |
C9—C5—C6—C2 | 73.87 (10) | C1—C11—N—C12 | 54.71 (13) |
C8—C7—C6—C5 | −6.73 (11) | C10—C11—N—C12 | −56.96 (13) |
C1—C7—C6—C5 | 103.57 (10) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N—H1H···O1i | 0.924 (17) | 1.988 (17) | 2.9094 (13) | 174.4 (15) |
O2—H2H···O1ii | 0.83 (2) | 2.19 (2) | 2.9214 (13) | 147.2 (17) |
O2—H2H···O1 | 0.83 (2) | 2.237 (19) | 2.7213 (12) | 117.7 (16) |
O3—H3H···O2iii | 0.89 (2) | 1.92 (2) | 2.7844 (13) | 164.4 (19) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, y, −z−1/2; (iii) x, −y, z+1/2. |
Experimental details
Crystal data |
Chemical formula | C12H13NO3 |
Mr | 219.23 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 173 |
a, b, c (Å) | 22.0040 (11), 6.3299 (3), 13.6153 (7) |
β (°) | 95.426 (3) |
V (Å3) | 1887.88 (16) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.38 × 0.29 × 0.29 |
|
Data collection |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7588, 2354, 1973 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.668 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.107, 1.06 |
No. of reflections | 2354 |
No. of parameters | 157 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.38, −0.21 |
Selected bond lengths (Å) topC12—C8 | 1.5189 (16) | C9—C5 | 1.5539 (16) |
C8—C9 | 1.5442 (16) | C9—C10 | 1.5719 (15) |
C8—C7 | 1.5455 (17) | C5—C4 | 1.5365 (17) |
C7—C1 | 1.5654 (15) | C5—C6 | 1.5430 (18) |
C7—C6 | 1.5655 (17) | C6—C2 | 1.5738 (16) |
C1—C11 | 1.5341 (17) | C2—C3 | 1.5489 (17) |
C1—C2 | 1.5588 (17) | C3—C4 | 1.5376 (17) |
C11—C10 | 1.5368 (16) | C3—C10 | 1.5431 (16) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N—H1H···O1i | 0.924 (17) | 1.988 (17) | 2.9094 (13) | 174.4 (15) |
O2—H2H···O1ii | 0.83 (2) | 2.19 (2) | 2.9214 (13) | 147.2 (17) |
O2—H2H···O1 | 0.83 (2) | 2.237 (19) | 2.7213 (12) | 117.7 (16) |
O3—H3H···O2iii | 0.89 (2) | 1.92 (2) | 2.7844 (13) | 164.4 (19) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, y, −z−1/2; (iii) x, −y, z+1/2. |
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The present study is part of an ongoing investigation of the chemical reactivity and solid-state structures of polycyclic pentacycloundecane (PCU) cage derivatives.
The title compound, (I), was first synthesized by Martins et al. (1993). It forms a hydrate (1:1) complex with water, and the crystal structure of the hydrate was reported by Kruger et al. (1996). The crystal structure of the lactam hydrate was, however, disordered and more accurate data about the structure of the lactam was required for our computational studies. The crystal structure of pure lactam without water is reported here.
The molecule of (I) consists of a large apolar (lipophilic) hydrocarbon skeleton and more polar dihydroxy and lactam parts (Fig. 1). A number of publications have focused on the molecular geometries of PCU cage derivatives (Flippen-Anderson et al., 1991; Linden et al., 2005; Kruger et al., 2005), and it has been reported that these compounds exhibit C—C bond lengths deviating from the normal value of 1.54 Å.
In (I), the C9—C10 [1.5719 (15) Å] bond, as well as the bonds constituting the cyclobutane ring, C1—C2 [1.5588 (17) Å], C2—C6 [1.5738 (16) Å], C6—C7 [1.5655 (17) Å] and C7—C1 [1.5654 (15) Å], are longer than expected, while the bonds involving atoms C4 and C11 (Table 1) are shorter than expected. On the other hand, the C8—C12 [1.5189 (16) Å] bond is very short.
In the crystal structure of (I), molecules are arranged to form a bilayer consisting of alternating lipophilic and polar layers. The lipophilic layer contains the PCU cage groups, while the hydroxy, ketone and amino groups constitute the polar layer. In the polar layer, a complex intermolecular hydrogen-bonding network, involving atoms N, O2 and O3 as hydrogen-bond donors and atoms O1 and O2 as hydrogen-bond acceptors, is formed (Table 2). These interactions result in two-dimensional hydrogen-bonded sheets of molecules (Fig. 2).