Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768109008271/gw5002sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768109008271/gw50021sup2.hkl |
CCDC reference: 742425
Data collection: ASTRO (5.007), BRUKER AXS; cell refinement: SAINT (5.007),BRUKER AXS; data reduction: SORTAV, J. Appl. Cryst. 1997, 30, 421; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: MOLLY, Acta Cryst. 1978, A34, 909.
C8H9NO2 | Z = 4 |
Mr = 151.16 | F(000) = 320 |
Monoclinic, P21/n | Dx = 1.337 Mg m−3 |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 7.0915 (3) Å | µ = 0.10 mm−1 |
b = 9.2149 (4) Å | T = 100 K |
c = 11.6015 (5) Å | Block, colorless |
β = 97.865 (1)° | 0.42 × 0.35 × 0.28 mm |
V = 751.00 (6) Å3 |
SMART 1000 CCD diffractometer | 9441 independent reflections |
Radiation source: fine-focus sealed tube | 6435 reflections with I > 3 σ(I) |
Graphite monochromator | Rint = 0.025 |
CCD scans | θmax = 59.5°, θmin = 2.3° |
Absorption correction: empirical (using intensity measurements) Empirical absorption correction using spherical harmonics, implemented in SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10 Ratio of minimum to maximum apparent transmission: 0.932780 | h = −17→16 |
Tmin = ?, Tmax = ? | k = −21→20 |
45383 measured reflections | l = −25→28 |
Refinement on F | 0 restraints |
Least-squares matrix: full | Only H-atom displacement parameters refined |
R[F2 > 2σ(F2)] = 0.018 | w1 = 1/[s2(Fo)] |
wR(F2) = 0.021 | (Δ/σ)max < 0.001 |
S = 0.89 | Δρmax = 0.10 e Å−3 |
6435 reflections | Δρmin = −0.09 e Å−3 |
278 parameters |
C8H9NO2 | V = 751.00 (6) Å3 |
Mr = 151.16 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.0915 (3) Å | µ = 0.10 mm−1 |
b = 9.2149 (4) Å | T = 100 K |
c = 11.6015 (5) Å | 0.42 × 0.35 × 0.28 mm |
β = 97.865 (1)° |
SMART 1000 CCD diffractometer | 9441 independent reflections |
Absorption correction: empirical (using intensity measurements) Empirical absorption correction using spherical harmonics, implemented in SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10 Ratio of minimum to maximum apparent transmission: 0.932780 | 6435 reflections with I > 3 σ(I) |
Tmin = ?, Tmax = ? | Rint = 0.025 |
45383 measured reflections |
R[F2 > 2σ(F2)] = 0.018 | 0 restraints |
wR(F2) = 0.021 | Only H-atom displacement parameters refined |
S = 0.89 | Δρmax = 0.10 e Å−3 |
6435 reflections | Δρmin = −0.09 e Å−3 |
278 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. |
x | y | z | Uiso*/Ueq | ||
O4 | 0.83573 (3) | 0.42321 (3) | 0.27736 (2) | 0.01706 (4) | |
O8 | 0.64663 (3) | −0.00573 (3) | 0.69136 (2) | 0.01838 (4) | |
N7 | 0.94805 (3) | 0.05129 (3) | 0.66039 (2) | 0.01249 (3) | |
C1 | 0.91188 (3) | 0.14266 (3) | 0.56170 (2) | 0.01120 (3) | |
C4 | 0.86614 (4) | 0.33084 (3) | 0.37039 (2) | 0.01256 (4) | |
C5 | 0.71954 (4) | 0.23699 (3) | 0.39018 (3) | 0.01348 (4) | |
C3 | 1.03765 (4) | 0.32839 (3) | 0.44549 (3) | 0.01501 (4) | |
C2 | 1.05982 (4) | 0.23486 (3) | 0.54034 (3) | 0.01437 (4) | |
C6 | 0.74178 (4) | 0.14284 (3) | 0.48505 (2) | 0.01286 (4) | |
C8 | 0.82133 (4) | −0.01424 (3) | 0.71961 (2) | 0.01300 (4) | |
C9 | 0.90728 (5) | −0.10118 (4) | 0.82381 (3) | 0.01874 (5) | |
H5 | 0.5979 (11) | 0.2363 (9) | 0.3336 (7) | 0.0225 (17)* | |
H6 | 0.6418 (11) | 0.0753 (9) | 0.4966 (7) | 0.0229 (18)* | |
H7 | 1.0732 (13) | 0.0417 (10) | 0.6873 (8) | 0.0275 (19)* | |
H2 | 1.1805 (13) | 0.2325 (10) | 0.5948 (8) | 0.031 (2)* | |
H3 | 1.1445 (12) | 0.3910 (9) | 0.4320 (8) | 0.0241 (18)* | |
H4 | 0.9525 (14) | 0.4582 (11) | 0.2571 (9) | 0.039 (2)* | |
H91 | 0.8355 (14) | −0.0857 (12) | 0.8877 (9) | 0.040 (2)* | |
H92 | 0.8966 (15) | −0.2061 (13) | 0.8084 (9) | 0.048 (3)* | |
H93 | 1.0408 (15) | −0.0847 (12) | 0.8453 (10) | 0.046 (3)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O4 | 0.01154 (6) | 0.02147 (9) | 0.01759 (9) | −0.00089 (6) | −0.00013 (6) | 0.00716 (7) |
O8 | 0.01103 (6) | 0.02696 (11) | 0.01771 (9) | −0.00229 (6) | 0.00395 (6) | 0.00081 (8) |
N7 | 0.00982 (6) | 0.01473 (8) | 0.01291 (7) | −0.00067 (5) | 0.00160 (5) | 0.00145 (6) |
C1 | 0.00945 (6) | 0.01256 (8) | 0.01153 (7) | −0.00088 (5) | 0.00127 (6) | −0.00059 (6) |
C4 | 0.01022 (7) | 0.01412 (8) | 0.01308 (8) | −0.00037 (6) | 0.00072 (6) | 0.00092 (7) |
C5 | 0.00991 (7) | 0.01622 (9) | 0.01381 (9) | −0.00154 (6) | −0.00017 (6) | 0.00065 (7) |
C3 | 0.01108 (7) | 0.01729 (10) | 0.01593 (10) | −0.00358 (7) | −0.00077 (7) | 0.00337 (8) |
C2 | 0.01051 (7) | 0.01703 (9) | 0.01479 (9) | −0.00334 (6) | −0.00104 (7) | 0.00253 (8) |
C6 | 0.00975 (7) | 0.01498 (9) | 0.01355 (8) | −0.00226 (6) | 0.00053 (6) | 0.00009 (7) |
C8 | 0.01216 (7) | 0.01399 (8) | 0.01334 (8) | −0.00111 (6) | 0.00353 (7) | −0.00060 (7) |
C9 | 0.01976 (11) | 0.01930 (11) | 0.01777 (11) | 0.00134 (9) | 0.00479 (9) | 0.00513 (9) |
O4—C4 | 1.3683 (4) | C5—C6 | 1.3934 (4) |
O4—H4 | 0.948 (10) | C5—H5 | 1.009 (8) |
O8—C8 | 1.2399 (4) | C3—C2 | 1.3896 (4) |
N7—C8 | 1.3465 (3) | C3—H3 | 0.982 (8) |
N7—C1 | 1.4160 (4) | C2—H2 | 0.992 (9) |
N7—H7 | 0.904 (9) | C6—H6 | 0.966 (8) |
C1—C6 | 1.3972 (4) | C8—C9 | 1.5077 (5) |
C1—C2 | 1.3982 (4) | C9—H91 | 0.966 (11) |
C4—C5 | 1.3953 (4) | C9—H92 | 0.985 (12) |
C4—C3 | 1.3960 (4) | C9—H93 | 0.958 (11) |
C4—O4—H4 | 111.0 (6) | C3—C2—C1 | 120.72 (2) |
C8—N7—C1 | 128.28 (2) | C3—C2—H2 | 120.8 (5) |
C8—N7—H7 | 118.2 (6) | C1—C2—H2 | 118.4 (5) |
C1—N7—H7 | 113.4 (6) | C5—C6—C1 | 119.87 (2) |
C6—C1—C2 | 119.33 (2) | C5—C6—H6 | 120.3 (5) |
C6—C1—N7 | 124.09 (2) | C1—C6—H6 | 119.8 (5) |
C2—C1—N7 | 116.57 (2) | O8—C8—N7 | 123.32 (3) |
O4—C4—C5 | 118.34 (2) | O8—C8—C9 | 121.69 (3) |
O4—C4—C3 | 122.15 (2) | N7—C8—C9 | 115.00 (3) |
C5—C4—C3 | 119.50 (3) | C8—C9—H91 | 109.8 (6) |
C6—C5—C4 | 120.63 (2) | C8—C9—H92 | 111.3 (6) |
C6—C5—H5 | 120.3 (5) | H91—C9—H92 | 104.4 (9) |
C4—C5—H5 | 119.1 (5) | C8—C9—H93 | 113.7 (7) |
C2—C3—C4 | 119.92 (2) | H91—C9—H93 | 112.5 (9) |
C2—C3—H3 | 119.0 (5) | H92—C9—H93 | 104.6 (9) |
C4—C3—H3 | 121.1 (5) |
Experimental details
Crystal data | |
Chemical formula | C8H9NO2 |
Mr | 151.16 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 100 |
a, b, c (Å) | 7.0915 (3), 9.2149 (4), 11.6015 (5) |
β (°) | 97.865 (1) |
V (Å3) | 751.00 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.42 × 0.35 × 0.28 |
Data collection | |
Diffractometer | SMART 1000 CCD diffractometer |
Absorption correction | Empirical (using intensity measurements) Empirical absorption correction using spherical harmonics, implemented in SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10 Ratio of minimum to maximum apparent transmission: 0.932780 |
No. of measured, independent and observed [I > 3 σ(I)] reflections | 45383, 9441, 6435 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 1.212 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.018, 0.021, 0.89 |
No. of reflections | 6435 |
No. of parameters | 278 |
H-atom treatment | Only H-atom displacement parameters refined |
Δρmax, Δρmin (e Å−3) | 0.10, −0.09 |
Computer programs: ASTRO (5.007), BRUKER AXS, SAINT (5.007),BRUKER AXS, SORTAV, J. Appl. Cryst. 1997, 30, 421, SHELXS97 (Sheldrick, 1990), MOLLY, Acta Cryst. 1978, A34, 909.