Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100007629/fr1281sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100007629/fr1281Isup2.hkl |
CCDC reference: 152603
Compound (I) was obtained as a column from a crystalline sample in Dr M. S. Newman's chemical collection. This was cut to provide the experimental sample. One synthesis, among others, is given by Boyd & Hansen (1953).
Fourier difference methods were used to locate initial H-atom positions, and these H atoms were refined. Refined C—H distances ranged from 0.96 (1) to 1.05 (1) Å, with a mean value of 0.99 (3) Å; their Uiso values ranged from 0.96 to 1.5 times the Ueq values of the attached C atoms. The ring H atoms were then made canonical, with C—H = 0.98 Å and Uiso = 1.2 × Ueq of the attached C atom.
Data collection: COLLECT (Nonius, 1999); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: TEXSAN (Molecular Structure Corporation, 1992-1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN and PLATON (Spek, 1990).
C11H15NO2 | F(000) = 416 |
Mr = 193.24 | Dx = 1.282 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.4286 (2) Å | Cell parameters from 22319 reflections |
b = 9.1195 (2) Å | θ = 1.9–27.5° |
c = 11.3748 (2) Å | µ = 0.09 mm−1 |
β = 112.2995 (11)° | T = 150 K |
V = 1000.88 (3) Å3 | Cut column, colourless |
Z = 4 | 0.35 × 0.27 × 0.27 mm |
Nonius KappaCCD diffractometer | 1936 reflections with I > 2σ(I) |
Radiation source: X-ray tube | Rint = 0.032 |
Graphite monochromator | θmax = 27.5° |
ω scans with κ offsets | h = −13→13 |
22319 measured reflections | k = −11→11 |
2293 independent reflections | l = −14→14 |
Refinement on F2 | 167 parameters |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.038 | Weighting scheme based on measured s.u.'s w = 1/[σ2cs + (0.032I)2] |
wR(F2) = 0.098 | (Δ/σ)max < 0.001 |
S = 1.97 | Δρmax = 0.23 e Å−3 |
2293 reflections | Δρmin = −0.22 e Å−3 |
C11H15NO2 | V = 1000.88 (3) Å3 |
Mr = 193.24 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.4286 (2) Å | µ = 0.09 mm−1 |
b = 9.1195 (2) Å | T = 150 K |
c = 11.3748 (2) Å | 0.35 × 0.27 × 0.27 mm |
β = 112.2995 (11)° |
Nonius KappaCCD diffractometer | 1936 reflections with I > 2σ(I) |
22319 measured reflections | Rint = 0.032 |
2293 independent reflections |
R[F2 > 2σ(F2)] = 0.038 | 167 parameters |
wR(F2) = 0.098 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.97 | Δρmax = 0.23 e Å−3 |
2293 reflections | Δρmin = −0.22 e Å−3 |
Experimental. The Laue group assignment, the systematic absences and the centrosymmetry indicated by the intensity statistics led to assignment of the space group uniquely as P21/n (No. 14); since refinement proceeded well, it was adopted. The maximum peak in the final difference map occurs ~0.7 Å from C8, the maximum negative peak ~0.8 Å from N1. |
Geometry. Table of Least-Squares Planes —————————— ————– Plane number 1 ————— Atoms Defining Plane Distance e.s.d. C1 (1) 0.0004 0.0009 C2 (1) 0.0034 0.0010 C3 (1) −0.0043 0.0010 C4 (1) −0.0006 0.0010 C5 (1) 0.0053 0.0011 C6 (1) −0.0049 0.0010 Mean deviation from plane is 0.0032 angstroms Chi-squared: 82.1 ————– Plane number 2 ————— Atoms Defining Plane Distance e.s.d. C7 (1) 0.0000 O1 (1) 0.0000 N1 (1) 0.0000 Additional Atoms Distance H1N1 (1) 0.0286 C8 (1) 0.2295 Mean deviation from plane is 0.0000 angstroms Chi-squared: 0.0 Dihedral angles between least-squares planes plane plane angle 2 1 25.78 ————– Plane number 3 ————— Atoms Defining Plane Distance e.s.d. C1 (2) −0.0004 0.0009 C2 (2) −0.0034 0.0010 C3 (2) 0.0043 0.0010 C4 (2) 0.0006 0.0010 C5 (2) −0.0053 0.0011 C6 (2) 0.0049 0.0010 Mean deviation from plane is 0.0032 angstroms Chi-squared: 82.1 Dihedral angles between least-squares planes plane plane angle 3 1 67.22 3 2 59.80 |
x | y | z | Uiso*/Ueq | ||
O1 | 0.38115 (7) | 0.94206 (8) | 0.59498 (6) | 0.0300 (2) | |
O2 | 0.19580 (8) | 0.73133 (9) | 0.54108 (7) | 0.0339 (2) | |
N1 | 0.47517 (9) | 0.80918 (9) | 0.77665 (8) | 0.0222 (2) | |
C1 | 0.55789 (10) | 1.05709 (11) | 0.76738 (9) | 0.0209 (3) | |
C2 | 0.61404 (10) | 1.08217 (11) | 0.89781 (9) | 0.0251 (3) | |
C3 | 0.69892 (11) | 1.20288 (12) | 0.94623 (9) | 0.0282 (3) | |
C4 | 0.72969 (11) | 1.29820 (11) | 0.86598 (10) | 0.0282 (3) | |
C5 | 0.67476 (11) | 1.27313 (12) | 0.73615 (10) | 0.0274 (3) | |
C6 | 0.58854 (10) | 1.15414 (11) | 0.68683 (9) | 0.0246 (3) | |
C7 | 0.46428 (10) | 0.93037 (11) | 0.70703 (9) | 0.0217 (3) | |
C8 | 0.40992 (10) | 0.66479 (11) | 0.72703 (9) | 0.0216 (3) | |
C9 | 0.25125 (11) | 0.67532 (12) | 0.66639 (10) | 0.0267 (3) | |
C10 | 0.46951 (12) | 0.60438 (13) | 0.63300 (10) | 0.0280 (3) | |
C11 | 0.44665 (12) | 0.56344 (13) | 0.84169 (10) | 0.0288 (3) | |
H1N1 | 0.5361 (13) | 0.8083 (14) | 0.8512 (12) | 0.039 (4)* | |
H1O2 | 0.2495 (16) | 0.8077 (18) | 0.5421 (14) | 0.070 (5)* | |
H2 | 0.5937 | 1.0146 | 0.9555 | 0.030* | |
H3 | 0.7374 | 1.2207 | 1.0381 | 0.034* | |
H4 | 0.7900 | 1.3829 | 0.9008 | 0.034* | |
H5 | 0.6970 | 1.3398 | 0.6790 | 0.033* | |
H6 | 0.5488 | 1.1380 | 0.5948 | 0.030* | |
H9A | 0.2203 (11) | 0.7366 (13) | 0.7255 (10) | 0.029 (3)* | |
H9B | 0.2152 (11) | 0.5747 (13) | 0.6633 (10) | 0.026 (3)* | |
H10A | 0.4260 (12) | 0.5107 (15) | 0.6003 (10) | 0.037 (3)* | |
H10B | 0.4531 (12) | 0.6744 (13) | 0.5606 (10) | 0.033 (3)* | |
H10C | 0.5732 (13) | 0.5886 (12) | 0.6787 (10) | 0.033 (3)* | |
H11A | 0.4125 (12) | 0.4573 (15) | 0.8106 (10) | 0.038 (3)* | |
H11B | 0.5461 (14) | 0.5600 (14) | 0.8882 (11) | 0.043 (3)* | |
H11C | 0.4041 (13) | 0.5977 (14) | 0.9010 (11) | 0.043 (3)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0337 (4) | 0.0274 (4) | 0.0192 (4) | −0.0051 (3) | −0.0009 (3) | 0.0043 (3) |
O2 | 0.0291 (5) | 0.0295 (5) | 0.0275 (4) | −0.0047 (4) | −0.0068 (3) | 0.0054 (3) |
N1 | 0.0233 (5) | 0.0206 (5) | 0.0165 (4) | −0.0012 (4) | 0.0008 (4) | 0.0020 (3) |
C1 | 0.0191 (5) | 0.0195 (5) | 0.0220 (5) | 0.0033 (4) | 0.0055 (4) | 0.0005 (4) |
C2 | 0.0275 (6) | 0.0245 (6) | 0.0225 (5) | 0.0026 (4) | 0.0085 (4) | 0.0010 (4) |
C3 | 0.0287 (6) | 0.0282 (6) | 0.0235 (5) | 0.0030 (5) | 0.0052 (5) | −0.0063 (4) |
C4 | 0.0240 (6) | 0.0204 (6) | 0.0362 (6) | 0.0004 (4) | 0.0069 (5) | −0.0051 (5) |
C5 | 0.0275 (6) | 0.0231 (5) | 0.0308 (6) | −0.0001 (4) | 0.0102 (5) | 0.0022 (4) |
C6 | 0.0264 (6) | 0.0230 (6) | 0.0221 (5) | 0.0026 (4) | 0.0066 (4) | 0.0018 (4) |
C7 | 0.0231 (5) | 0.0225 (5) | 0.0181 (5) | 0.0012 (4) | 0.0064 (4) | 0.0014 (4) |
C8 | 0.0230 (5) | 0.0188 (5) | 0.0193 (5) | −0.0013 (4) | 0.0036 (4) | 0.0013 (4) |
C9 | 0.0244 (6) | 0.0274 (6) | 0.0240 (5) | −0.0011 (5) | 0.0043 (5) | 0.0006 (5) |
C10 | 0.0316 (6) | 0.0235 (6) | 0.0287 (6) | −0.0019 (5) | 0.0110 (5) | −0.0023 (5) |
C11 | 0.0322 (7) | 0.0237 (6) | 0.0248 (5) | −0.0013 (5) | 0.0043 (5) | 0.0047 (5) |
O1—C7 | 1.2446 (11) | C5—C6 | 1.3849 (15) |
O2—C9 | 1.4148 (13) | C5—H5 | 0.98 |
O2—H1O2 | 0.890 (16) | C6—H6 | 0.98 |
N1—C7 | 1.3391 (12) | C8—C9 | 1.5352 (14) |
N1—C8 | 1.4913 (12) | C8—C10 | 1.5292 (14) |
N1—H1N1 | 0.845 (13) | C8—C11 | 1.5241 (14) |
C1—C2 | 1.3918 (13) | C9—H9B | 0.987 (11) |
C1—C6 | 1.3954 (14) | C9—H9A | 1.017 (11) |
C1—C7 | 1.5004 (14) | C10—H10A | 0.973 (13) |
C2—C3 | 1.3888 (15) | C10—H10B | 1.004 (11) |
C2—H2 | 0.98 | C10—H10C | 1.016 (12) |
C3—C4 | 1.3835 (15) | C11—H11A | 1.045 (13) |
C3—H3 | 0.98 | C11—H11B | 0.969 (13) |
C4—C5 | 1.3853 (15) | C11—H11C | 0.988 (13) |
C4—H4 | 0.98 | ||
C9—O2—H1O2 | 104.7 (9) | N1—C8—C9 | 111.97 (8) |
C7—N1—C8 | 125.51 (8) | N1—C8—C10 | 109.55 (8) |
C7—N1—H1N1 | 117.6 (9) | N1—C8—C11 | 106.33 (8) |
C8—N1—H1N1 | 115.7 (9) | C9—C8—C10 | 111.29 (8) |
C2—C1—C6 | 119.16 (9) | C9—C8—C11 | 107.49 (8) |
C2—C1—C7 | 123.49 (9) | C10—C8—C11 | 110.07 (9) |
C6—C1—C7 | 117.36 (8) | O2—C9—C8 | 115.73 (8) |
C1—C2—C3 | 120.00 (9) | O2—C9—H9B | 107.2 (6) |
C1—C2—H2 | 120.0 | O2—C9—H9A | 110.9 (6) |
C3—C2—H2 | 120.0 | C8—C9—H9B | 106.8 (6) |
C2—C3—C4 | 120.59 (9) | C8—C9—H9A | 107.2 (6) |
C2—C3—H3 | 119.7 | H9B—C9—H9A | 108.8 (9) |
C4—C3—H3 | 119.7 | C8—C10—H10B | 110.9 (6) |
C3—C4—C5 | 119.61 (10) | C8—C10—H10C | 109.2 (6) |
C3—C4—H4 | 120.2 | C8—C10—H10A | 109.2 (6) |
C5—C4—H4 | 120.2 | H10B—C10—H10C | 109.1 (9) |
C4—C5—C6 | 120.23 (9) | H10B—C10—H10A | 109.6 (9) |
C4—C5—H5 | 119.9 | H10C—C10—H10A | 108.8 (9) |
C6—C5—H5 | 119.9 | C8—C11—H11B | 110.8 (7) |
C1—C6—C5 | 120.41 (9) | C8—C11—H11C | 111.1 (7) |
C1—C6—H6 | 119.8 | C8—C11—H11A | 109.2 (6) |
C5—C6—H6 | 119.8 | H11B—C11—H11C | 107.6 (9) |
O1—C7—N1 | 123.10 (9) | H11B—C11—H11A | 108.1 (10) |
O1—C7—C1 | 118.81 (9) | H11C—C11—H11A | 109.9 (10) |
N1—C7—C1 | 118.08 (8) | ||
O1—C7—N1—C8 | 10.89 (16) | C1—C7—N1—C8 | −168.61 (9) |
O1—C7—C1—C2 | 154.49 (10) | C2—C1—C6—C5 | 0.60 (14) |
O1—C7—C1—C6 | −25.19 (13) | C2—C3—C4—C5 | 0.27 (15) |
O2—C9—C8—N1 | 79.90 (11) | C3—C2—C1—C6 | 0.26 (15) |
O2—C9—C8—C10 | −43.09 (13) | C3—C2—C1—C7 | −179.42 (9) |
O2—C9—C8—C11 | −163.68 (9) | C3—C4—C5—C6 | 0.59 (15) |
N1—C7—C1—C2 | −25.98 (14) | C5—C6—C1—C7 | −179.70 (9) |
N1—C7—C1—C6 | 154.33 (9) | C7—N1—C8—C9 | −60.68 (12) |
C1—C2—C3—C4 | −0.70 (15) | C7—N1—C8—C10 | 63.28 (12) |
C1—C6—C5—C4 | −1.03 (15) | C7—N1—C8—C11 | −177.80 (9) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H1O2···O1 | 0.89 (2) | 1.77 (2) | 2.6279 (11) | 162 (1) |
N1—H1N1···O2i | 0.85 (2) | 2.20 (2) | 3.0374 (11) | 171 (1) |
C2—H2···O2i | 0.98 | 2.52 | 3.2407 (13) | 131 |
C4—H4···O1ii | 0.98 | 2.60 | 3.4305 (12) | 143 |
C6—H6···O1iii | 0.98 | 2.63 | 3.4517 (12) | 141 |
C11—H11B···O2i | 0.97 (2) | 2.65 (2) | 3.3054 (14) | 125 (1) |
Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) x+1/2, −y+5/2, z+1/2; (iii) −x+1, −y+2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C11H15NO2 |
Mr | 193.24 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 150 |
a, b, c (Å) | 10.4286 (2), 9.1195 (2), 11.3748 (2) |
β (°) | 112.2995 (11) |
V (Å3) | 1000.88 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.35 × 0.27 × 0.27 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 22319, 2293, 1936 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.098, 1.97 |
No. of reflections | 2293 |
No. of parameters | 167 |
No. of restraints | ? |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.23, −0.22 |
Computer programs: COLLECT (Nonius, 1999), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXS86 (Sheldrick, 1990), TEXSAN (Molecular Structure Corporation, 1992-1997), ORTEPII (Johnson, 1976), TEXSAN and PLATON (Spek, 1990).
O1—C7 | 1.2446 (11) | N1—C8 | 1.4913 (12) |
O2—C9 | 1.4148 (13) | C1—C7 | 1.5004 (14) |
N1—C7 | 1.3391 (12) | ||
C7—N1—C8 | 125.51 (8) | O1—C7—C1 | 118.81 (9) |
C2—C1—C7 | 123.49 (9) | N1—C7—C1 | 118.08 (8) |
C6—C1—C7 | 117.36 (8) | O2—C9—C8 | 115.73 (8) |
O1—C7—N1 | 123.10 (9) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H1O2···O1 | 0.89 (2) | 1.77 (2) | 2.6279 (11) | 161.8 (14) |
N1—H1N1···O2i | 0.85 (2) | 2.20 (2) | 3.0374 (11) | 171.0 (12) |
C2—H2···O2i | 0.98 | 2.52 | 3.2407 (13) | 131 |
C4—H4···O1ii | 0.98 | 2.60 | 3.4305 (12) | 143 |
C6—H6···O1iii | 0.98 | 2.63 | 3.4517 (12) | 141 |
C11—H11B···O2i | 0.97 (2) | 2.65 (2) | 3.3054 (14) | 125.2 (9) |
Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) x+1/2, −y+5/2, z+1/2; (iii) −x+1, −y+2, −z+1. |
a | b | c | d | e | f | |
a | S(7) | C22(6) | C22(7) | C21(12) | R42(20) | C22(8) |
b | C(5) | R21(7) | C22(14 | C22(12) | R21(6) | |
c | C(8) | C22(11) | C22(11) | R21(9) | ||
d | C(7) | C21(6) | C22(16) | |||
e | R22(10) | C22(14) | ||||
f | C(5) |
This report is one of a series on hydrogen bonding and C—H···O interactions in aromatic compounds. The title compound, (I), crystallized in the centrosymmetric space group P21/n with one molecule as the asymmetric unit. The refined molecule and the labelling scheme are given in Fig. 1. \sch
Two hydrogen bonds, one of them intramolecular, and four leading intermolecular C—H···O interactions (Taylor & Kennard, 1982; Steiner & Desiraju, 1998) are present in this structure. The geometric parameters of these are given in Table 2. A central molecule is linked directly to five neighbouring molecules by the tabulated interactions, as shown in the stereodiagram (Fig. 2). The results of basic first- and second-level graph-set analysis (Bernstein et al., 1995) involving these interactions, labelled a-f for this purpose in the order of their appearance in Table 2, are given in Table 3. Among the twenty-one patterns fifteen are chains, which propagate variously along [101] (8), [010] (5) and [111] (2). Since only two of three such vectors are linearly independent, however, the resulting network of interactions is two-dimensional. Of the five ring patterns, two are disposed about centres of symmetry.
The phenyl ring is nearly planar, the maximum deviation of a ring atom from the best-fit plane describing them being 0.0053 (11) Å. The dihedral angle between this plane and that of the amide group atoms C7, O1 and N1 is 25.77 (12)°. This angle is apparent in Fig. 2.
Selected bond distances and angles of (I) are given in Table 1. A l l distances and angles fall within normal limits. For structural comparisons of the aliphatic amide portion of (I), the structure of 4,6-dimethyl-3-(4,4-dimethyl-2-oxazolinyl)-N-(2-hydroxy-1,1-dimethylethyl) salicylamide [Inamoto et al., 1996; hereinafter (II)] appears to be the best available, although the s.u.s are almost ten times those of the present study. For the eight pairs of corresponding non-H interatomic distances in the aliphatic amide substructures of (I) and (II), the greatest difference is just twice the s.u. of that distance given for (II), so these results are in good agreement. The orientation of this group with respect to the attached phenyl ring, however, is quite different in the two molecules, since in (II) the dihedral angle between the best-fit phenyl plane and the amide plane as defined above is 88.4 (9)°. In view of the four additional substituents on the phenyl ring of (II), two of them capable of hydrogen bonding, this difference is not problematic. In (I) the closest intermolecular approaches, excluding pairs of atoms involved in the hydrogen-bonding groups or the tabulated C—H···O interactions, are between H2 and H9Bi [symmetry code: (i) 1/2 + x, 3/2 − y, 1/2 + z] and fall short of the corresponding Bondi (1964) van der Waals radius sum by 0.04 Å.