Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S010876810501637X/lc5024sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S010876810501637X/lc5024sup2.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S010876810501637X/lc5024sup3.pdf | |
Portable Document Format (PDF) file https://doi.org/10.1107/S010876810501637X/lc5024sup4.pdf | |
Portable Document Format (PDF) file https://doi.org/10.1107/S010876810501637X/lc5024sup5.pdf |
CCDC reference: 280359
Data collection: SMART (Bruker, 1997-2001); cell refinement: SAINT (Bruker, 1997-2001); data reduction: SAINT (Bruker, 1997-2001); program(s) used to refine structure: Koritsanszky et al., (2003); molecular graphics: Koritsanszky et al., (2003); software used to prepare material for publication: Koritsanszky et al., (2003).
C17H19NO3·H2O | Z = 4 |
Mr = 303.35 | F(000) = 648 |
Orthorhombic, P212121 | Dx = 1.318 Mg m−3 |
Hall symbol: P 2ac 2ab | Mo Kα radiation, λ = 0.7107 Å |
a = 7.431 (6) Å | µ = 0.09 mm−1 |
b = 13.769 (9) Å | T = 25 K |
c = 14.944 (13) Å | Prism, colourless |
V = 1529 (2) Å3 | 0.5 × 0.35 × 0.35 mm |
Bruker SMART Apex CCD Detector
on Huber four circle diffractometer | Rint = 0.04 |
ϕ scans | θmax = 54.6° |
67606 measured reflections | h = −16→17 |
9984 independent reflections | k = −29→25 |
8069 reflections with I > 3 σ(I) | l = −33→32 |
Refinement on F | 0 restraints |
Least-squares matrix: full | Only H-atom displacement parameters refined |
R[F2 > 2σ(F2)] = 0.023 | w1 = 1/[s2(Fo)] |
wR(F2) = 0.020 | (Δ/σ)max = 0.000047 |
S = 0.65 | Δρmax = 0.22 e Å−3 |
8069 reflections | Δρmin = −0.20 e Å−3 |
682 parameters |
C17H19NO3·H2O | V = 1529 (2) Å3 |
Mr = 303.35 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 7.431 (6) Å | µ = 0.09 mm−1 |
b = 13.769 (9) Å | T = 25 K |
c = 14.944 (13) Å | 0.5 × 0.35 × 0.35 mm |
Bruker SMART Apex CCD Detector
on Huber four circle diffractometer | 8069 reflections with I > 3 σ(I) |
67606 measured reflections | Rint = 0.04 |
9984 independent reflections |
R[F2 > 2σ(F2)] = 0.023 | 0 restraints |
wR(F2) = 0.020 | Only H-atom displacement parameters refined |
S = 0.65 | Δρmax = 0.22 e Å−3 |
8069 reflections | Δρmin = −0.20 e Å−3 |
682 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
x | y | z | Uiso*/Ueq | ||
O1 | 0.61639 (7) | 0.89628 (3) | 0.26177 (4) | 0.0091 (1) | |
O2 | 0.71984 (7) | 0.65587 (4) | 0.47286 (3) | 0.0091 (1) | |
O3 | 0.87996 (7) | 0.76148 (3) | 0.33796 (3) | 0.0072 (1) | |
N1 | 1.18029 (6) | 0.49795 (3) | 0.12824 (3) | 0.0071 (1) | |
C1 | 0.69069 (7) | 0.71688 (3) | 0.07852 (3) | 0.0086 (1) | |
C2 | 0.63118 (7) | 0.80010 (3) | 0.12507 (3) | 0.0087 (1) | |
C3 | 0.69205 (6) | 0.82259 (3) | 0.21303 (3) | 0.0073 (1) | |
C4 | 0.82078 (6) | 0.75969 (3) | 0.24963 (3) | 0.0065 (1) | |
C5 | 0.95874 (6) | 0.66546 (3) | 0.35590 (3) | 0.0065 (1) | |
C6 | 0.82277 (6) | 0.60129 (3) | 0.40948 (3) | 0.0070 (1) | |
C7 | 0.69673 (6) | 0.54364 (3) | 0.34986 (3) | 0.0076 (1) | |
C8 | 0.75891 (6) | 0.49860 (3) | 0.27558 (3) | 0.0074 (1) | |
C9 | 0.98294 (6) | 0.49028 (3) | 0.14576 (3) | 0.0066 (1) | |
C10 | 0.86331 (7) | 0.55334 (3) | 0.08189 (3) | 0.0081 (1) | |
C11 | 0.81922 (6) | 0.65394 (3) | 0.11762 (3) | 0.0070 (1) | |
C12 | 0.88716 (6) | 0.68091 (3) | 0.20146 (3) | 0.0062 (1) | |
C13 | 1.00782 (6) | 0.62104 (3) | 0.26207 (3) | 0.0058 (1) | |
C14 | 0.95218 (6) | 0.51359 (3) | 0.24709 (3) | 0.0061 (1) | |
C15 | 1.20924 (6) | 0.63318 (3) | 0.23899 (3) | 0.0077 (1) | |
C16 | 1.25082 (6) | 0.59768 (3) | 0.14308 (3) | 0.0084 (1) | |
C17 | 1.23142 (7) | 0.46153 (4) | 0.03812 (3) | 0.0105 (1) | |
O4 | 0.44890 (8) | 0.77409 (4) | 0.40240 (4) | 0.0118 (1) | |
H1 | 0.63675 | 0.69882 | 0.01351 | 0.0230* | |
H2 | 0.52516 | 0.84457 | 0.09740 | 0.0160* | |
H5 | 1.07660 | 0.68080 | 0.39592 | 0.0140* | |
H6 | 0.90812 | 0.55165 | 0.44603 | 0.0120* | |
H7 | 0.55811 | 0.53646 | 0.37063 | 0.0110* | |
H8 | 0.67029 | 0.45254 | 0.23708 | 0.0110* | |
H9 | 0.95061 | 0.41431 | 0.13747 | 0.0150* | |
H10A | 0.76067 | 0.51950 | 0.07277 | 0.0100* | |
H10B | 0.91178 | 0.55452 | 0.02417 | 0.0150* | |
H11 | 0.70215 | 0.93157 | 0.29832 | 0.0220* | |
H14 | 1.03083 | 0.47030 | 0.28030 | 0.0110* | |
H15A | 1.28804 | 0.58871 | 0.28394 | 0.0110* | |
H15B | 1.24802 | 0.70863 | 0.24326 | 0.0150* | |
H16A | 1.39190 | 0.59833 | 0.12553 | 0.0190* | |
H16B | 1.19671 | 0.64491 | 0.09206 | 0.0150* | |
H17A | 1.16470 | 0.39354 | 0.02393 | 0.0140* | |
H17B | 1.37516 | 0.45018 | 0.03666 | 0.0110* | |
H17C | 1.19756 | 0.51204 | −0.01462 | 0.0130* | |
H21 | 0.79986 | 0.68554 | 0.51617 | 0.0210* | |
H41 | 0.54084 | 0.73178 | 0.42670 | 0.0160* | |
H42 | 0.49091 | 0.81435 | 0.35344 | 0.0110* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0074 (1) | 0.0074 (1) | 0.0124 (2) | 0.0021 (1) | −0.0010 (1) | −0.0020 (1) |
O2 | 0.0090 (1) | 0.0110 (1) | 0.0073 (1) | 0.0001 (1) | 0.0009 (1) | −0.0017 (1) |
O3 | 0.0085 (1) | 0.0060 (1) | 0.0071 (1) | 0.0009 (1) | −0.0010 (1) | −0.0006 (1) |
N1 | 0.0066 (1) | 0.0069 (1) | 0.0079 (1) | 0.0002 (1) | 0.0013 (1) | −0.0001 (1) |
C1 | 0.0099 (1) | 0.0082 (1) | 0.0076 (1) | 0.0018 (1) | −0.0024 (1) | 0.0002 (1) |
C2 | 0.0094 (1) | 0.0075 (1) | 0.0092 (1) | 0.0021 (1) | −0.0022 (1) | 0.0006 (1) |
C3 | 0.0068 (1) | 0.0063 (1) | 0.0089 (1) | 0.0013 (1) | −0.0009 (1) | −0.0002 (1) |
C4 | 0.0066 (1) | 0.0058 (1) | 0.0071 (1) | 0.0011 (1) | −0.0009 (1) | −0.0002 (1) |
C5 | 0.0064 (1) | 0.0065 (1) | 0.0065 (1) | −0.0001 (1) | −0.0008 (1) | −0.0002 (1) |
C6 | 0.0071 (1) | 0.0074 (1) | 0.0065 (1) | −0.0001 (1) | −0.0001 (1) | 0.0001 (1) |
C7 | 0.0063 (1) | 0.0088 (1) | 0.0077 (1) | −0.0009 (1) | 0.0008 (1) | −0.0008 (1) |
C8 | 0.0062 (1) | 0.0080 (1) | 0.0081 (1) | −0.0018 (1) | 0.0007 (1) | −0.0011 (1) |
C9 | 0.0066 (1) | 0.0059 (1) | 0.0072 (1) | 0.0003 (1) | 0.0003 (1) | −0.0002 (1) |
C10 | 0.0096 (1) | 0.0075 (1) | 0.0073 (1) | 0.0016 (1) | −0.0012 (1) | −0.0012 (1) |
C11 | 0.0080 (1) | 0.0065 (1) | 0.0066 (1) | 0.0011 (1) | −0.0014 (1) | −0.0002 (1) |
C12 | 0.0067 (1) | 0.0055 (1) | 0.0064 (1) | 0.0009 (1) | −0.0009 (1) | −0.0002 (1) |
C13 | 0.0051 (1) | 0.0055 (1) | 0.0068 (1) | −0.0001 (1) | −0.0003 (1) | −0.0001 (1) |
C14 | 0.0058 (1) | 0.0054 (1) | 0.0070 (1) | −0.0003 (1) | 0.0003 (1) | 0.0000 (1) |
C15 | 0.0059 (1) | 0.0075 (1) | 0.0096 (1) | −0.0006 (1) | 0.0002 (1) | −0.0006 (1) |
C16 | 0.0077 (1) | 0.0077 (1) | 0.0099 (1) | −0.0006 (1) | 0.0022 (1) | 0.0003 (1) |
C17 | 0.0113 (2) | 0.0107 (2) | 0.0096 (2) | 0.0016 (1) | 0.0028 (1) | −0.0009 (1) |
O4 | 0.0096 (2) | 0.0143 (2) | 0.0116 (2) | 0.0010 (1) | 0.0014 (1) | −0.0010 (2) |
O1—C3 | 1.3697 (7) | C10—C11 | 1.5202 (8) |
O2—C6 | 1.4307 (7) | C11—C12 | 1.4009 (8) |
O3—C4 | 1.3916 (7) | C12—C13 | 1.5179 (8) |
O3—C5 | 1.4706 (7) | C13—C15 | 1.5451 (8) |
O1—H11 | 0.9700 | C13—C14 | 1.5524 (8) |
O2—H21 | 0.9700 | C15—C16 | 1.5456 (8) |
O4—H41 | 0.9700 | C1—H1 | 1.0800 |
O4—H42 | 0.9700 | C2—H2 | 1.0800 |
N1—C16 | 1.4864 (8) | C5—H5 | 1.0800 |
N1—C9 | 1.4935 (8) | C6—H6 | 1.0800 |
N1—C17 | 1.4865 (8) | C7—H7 | 1.0800 |
C1—C11 | 1.4159 (8) | C8—H8 | 1.0800 |
C1—C2 | 1.4115 (8) | C9—H9 | 1.0800 |
C2—C3 | 1.4242 (8) | C10—H10A | 0.9000 |
C3—C4 | 1.4016 (8) | C10—H10B | 0.9300 |
C4—C12 | 1.3922 (8) | C14—H14 | 0.9700 |
C5—C6 | 1.5629 (8) | C15—H15B | 1.0800 |
C5—C13 | 1.5727 (8) | C15—H15A | 1.0800 |
C6—C7 | 1.5170 (8) | C16—H16B | 1.0800 |
C7—C8 | 1.3529 (8) | C16—H16A | 1.0800 |
C8—C14 | 1.5122 (8) | C17—H17C | 1.0800 |
C9—C10 | 1.5669 (8) | C17—H17A | 1.0800 |
C9—C14 | 1.5647 (8) | C17—H17B | 1.0800 |
C4—O3—C5 | 106.43 (4) | C9—C14—C13 | 107.23 (3) |
C3—O1—H11 | 114.00 | C13—C15—C16 | 111.50 (4) |
C6—O2—H21 | 110.00 | N1—C16—C15 | 111.10 (4) |
H41—O4—H42 | 114.00 | C11—C1—H1 | 119.00 |
C9—N1—C17 | 112.71 (4) | C2—C1—H1 | 121.00 |
C9—N1—C16 | 112.67 (4) | C1—C2—H2 | 120.00 |
C16—N1—C17 | 110.90 (4) | C3—C2—H2 | 118.00 |
C2—C1—C11 | 120.32 (4) | C6—C5—H5 | 111.00 |
C1—C2—C3 | 122.13 (4) | C13—C5—H5 | 112.00 |
O1—C3—C4 | 122.03 (4) | O3—C5—H5 | 104.00 |
C2—C3—C4 | 116.27 (4) | C5—C6—H6 | 104.00 |
O1—C3—C2 | 121.43 (4) | C7—C6—H6 | 109.00 |
O3—C4—C3 | 125.10 (4) | O2—C6—H6 | 108.00 |
C3—C4—C12 | 121.43 (4) | C8—C7—H7 | 121.00 |
O3—C4—C12 | 113.10 (4) | C6—C7—H7 | 118.00 |
C6—C5—C13 | 112.76 (3) | C14—C8—H8 | 121.00 |
O3—C5—C13 | 106.23 (4) | C7—C8—H8 | 120.00 |
O3—C5—C6 | 110.14 (4) | N1—C9—H9 | 105.00 |
O2—C6—C5 | 112.82 (4) | C10—C9—H9 | 110.00 |
O2—C6—C7 | 109.49 (4) | C14—C9—H9 | 106.00 |
C5—C6—C7 | 113.21 (4) | C9—C10—H10A | 107.00 |
C6—C7—C8 | 120.72 (4) | C9—C10—H10B | 111.00 |
C7—C8—C14 | 119.53 (4) | C11—C10—H10B | 113.00 |
C10—C9—C14 | 113.14 (3) | H10A—C10—H10B | 101.00 |
N1—C9—C10 | 114.28 (4) | C11—C10—H10A | 110.00 |
N1—C9—C14 | 107.37 (4) | C8—C14—H14 | 110.00 |
C9—C10—C11 | 114.41 (4) | C13—C14—H14 | 111.00 |
C1—C11—C12 | 116.74 (4) | C9—C14—H14 | 106.00 |
C1—C11—C10 | 123.93 (4) | C13—C15—H15A | 109.00 |
C10—C11—C12 | 118.55 (4) | C16—C15—H15A | 107.00 |
C11—C12—C13 | 127.06 (4) | C16—C15—H15B | 108.00 |
C4—C12—C11 | 122.77 (4) | H15A—C15—H15B | 111.00 |
C4—C12—C13 | 108.90 (4) | C13—C15—H15B | 110.00 |
C5—C13—C12 | 100.59 (3) | N1—C16—H16A | 108.00 |
C12—C13—C14 | 105.91 (3) | C15—C16—H16A | 115.00 |
C5—C13—C15 | 112.44 (4) | C15—C16—H16B | 113.00 |
C14—C13—C15 | 109.20 (3) | N1—C16—H16B | 109.00 |
C5—C13—C14 | 115.94 (4) | H16A—C16—H16B | 101.00 |
C12—C13—C15 | 112.35 (4) | N1—C17—H17B | 109.00 |
C8—C14—C13 | 110.03 (3) | N1—C17—H17C | 113.00 |
C8—C14—C9 | 112.53 (4) | N1—C17—H17A | 111.00 |
C5—O3—C4—C3 | 159.65 (4) | O2—C6—C7—C8 | 169.23 (4) |
C5—O3—C4—C12 | −13.41 (5) | C5—C6—C7—C8 | 42.41 (5) |
C4—O3—C5—C6 | −101.16 (4) | C6—C7—C8—C14 | −5.71 (6) |
C4—O3—C5—C13 | 21.24 (5) | C7—C8—C14—C9 | −158.76 (4) |
C17—N1—C16—C15 | −176.12 (4) | C7—C8—C14—C13 | −39.26 (5) |
C16—N1—C9—C10 | 63.19 (5) | C14—C9—C10—C11 | 30.61 (5) |
C16—N1—C9—C14 | −63.17 (5) | N1—C9—C10—C11 | −92.69 (5) |
C9—N1—C16—C15 | 56.49 (5) | C10—C9—C14—C8 | 58.61 (5) |
C17—N1—C9—C14 | 170.40 (4) | N1—C9—C14—C8 | −174.36 (3) |
C17—N1—C9—C10 | −63.24 (5) | N1—C9—C14—C13 | 64.53 (4) |
C11—C1—C2—C3 | −2.03 (7) | C10—C9—C14—C13 | −62.50 (5) |
C2—C1—C11—C12 | −2.50 (7) | C9—C10—C11—C12 | 0.16 (6) |
C2—C1—C11—C10 | 167.21 (4) | C9—C10—C11—C1 | −169.37 (4) |
C1—C2—C3—O1 | −171.51 (5) | C1—C11—C12—C4 | 6.50 (7) |
C1—C2—C3—C4 | 2.69 (7) | C10—C11—C12—C13 | 1.87 (7) |
O1—C3—C4—C12 | 175.36 (4) | C1—C11—C12—C13 | 172.16 (4) |
C2—C3—C4—O3 | −171.30 (4) | C10—C11—C12—C4 | −163.78 (4) |
O1—C3—C4—O3 | 2.85 (7) | C11—C12—C13—C5 | −154.18 (4) |
C2—C3—C4—C12 | 1.21 (6) | C11—C12—C13—C14 | −33.11 (6) |
C3—C4—C12—C13 | −173.95 (4) | C11—C12—C13—C15 | 86.04 (5) |
O3—C4—C12—C13 | −0.61 (5) | C4—C12—C13—C5 | 13.10 (4) |
C3—C4—C12—C11 | −6.01 (7) | C4—C12—C13—C14 | 134.17 (4) |
O3—C4—C12—C11 | 167.33 (4) | C4—C12—C13—C15 | −106.68 (4) |
O3—C5—C6—C7 | 88.80 (4) | C5—C13—C14—C8 | 47.75 (5) |
O3—C5—C13—C12 | −20.58 (4) | C5—C13—C14—C9 | 170.44 (4) |
C13—C5—C6—O2 | −154.71 (4) | C12—C13—C14—C8 | −62.81 (4) |
C13—C5—C6—C7 | −29.67 (5) | C5—C13—C15—C16 | −174.72 (3) |
O3—C5—C6—O2 | −36.25 (5) | C12—C13—C15—C16 | −62.08 (4) |
C6—C5—C13—C14 | −13.50 (5) | C14—C13—C15—C16 | 55.12 (5) |
C6—C5—C13—C15 | −140.13 (4) | C15—C13—C14—C9 | −61.33 (4) |
O3—C5—C13—C15 | 99.15 (4) | C12—C13—C14—C9 | 59.88 (4) |
C6—C5—C13—C12 | 100.15 (4) | C15—C13—C14—C8 | 175.98 (4) |
O3—C5—C13—C14 | −134.23 (4) | C13—C15—C16—N1 | −51.52 (5) |
Experimental details
Crystal data | |
Chemical formula | C17H19NO3·H2O |
Mr | 303.35 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 25 |
a, b, c (Å) | 7.431 (6), 13.769 (9), 14.944 (13) |
V (Å3) | 1529 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.5 × 0.35 × 0.35 |
Data collection | |
Diffractometer | Bruker SMART Apex CCD Detector
on Huber four circle diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 3 σ(I)] reflections | 67606, 9984, 8069 |
Rint | 0.04 |
(sin θ/λ)max (Å−1) | 1.147 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.023, 0.020, 0.65 |
No. of reflections | 8069 |
No. of parameters | 682 |
H-atom treatment | Only H-atom displacement parameters refined |
Δρmax, Δρmin (e Å−3) | 0.22, −0.20 |
Computer programs: SMART (Bruker, 1997-2001), SAINT (Bruker, 1997-2001), Koritsanszky et al., (2003).
O1—C3 | 1.3697 (7) | N1—C16 | 1.4864 (8) |
O2—C6 | 1.4307 (7) | N1—C9 | 1.4935 (8) |
O3—C4 | 1.3916 (7) | N1—C17 | 1.4865 (8) |
O3—C5 | 1.4706 (7) | ||
C4—O3—C5 | 106.43 (4) | O3—C5—C13 | 106.23 (4) |
C9—N1—C17 | 112.71 (4) | O3—C5—C6 | 110.14 (4) |
C9—N1—C16 | 112.67 (4) | O2—C6—C5 | 112.82 (4) |
C16—N1—C17 | 110.90 (4) | O2—C6—C7 | 109.49 (4) |
O1—C3—C4 | 122.03 (4) | N1—C9—C10 | 114.28 (4) |
O1—C3—C2 | 121.43 (4) | N1—C9—C14 | 107.37 (4) |
O3—C4—C3 | 125.10 (4) | N1—C16—C15 | 111.10 (4) |
O3—C4—C12 | 113.10 (4) |