Interplay between steric and electronic factors in determining the strength of intramolecular N—H...O resonance-assisted hydrogen bonds in β-enaminones

The crystal structures of five β-enaminones are reported: (2Z)-3-(benzylamino)-1,3-diphenyl-prop-2-en-1-one, (2Z)-3-(benz­yl­amino)-3-(2-hydroxyphenyl)-1-phenyl-prop-2-en-1-one, (2Z)-3-(benzylamino)-3-(4-methoxyphenyl)-1-(3-nitrophen­yl)-prop-2-en-1-one, 2-{1-[(4-methoxyphenyl)amino]ethylidene}cyclohexene-1,3-dione and 2-{1-[(3-methoxyphenyl)amino]­ethylidene}cyclohexene-1,3-dione. The structures were analysed and compared with those of similar compounds in order to establish which factors determine the range (2.53–2.72 Å) of N...O hydrogen-bond distances in intramolecularly hydrogen-bonded β-enaminones. It has been shown that, beyond electronic resonance-assisted hydrogen-bond effects modulated by substituents, the necessary requirements to produce very short N—H...O hydrogen bonding are steric intramolecular repulsions, including the embedding of an enaminonic C—C or C—N bond in an aliphatic six-membered ring. By considering the structural features it is possible to expect the strength of N—H...O hydrogen bonds adopted by specific β-enaminones.

Computing details

For all compounds, data collection: Kappa CCD Server Software (Nonius, 1997); cell refinement: DENZO SMN (Otwinowski & Minor, 1997); data reduction: DENZO SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP III (Burnett & Johnson, 1996). Software used to prepare material for publication: SHELXL97 (Sheldrick, 1997), PARST (Nardelli, 1995), PLATON (Spek, 2002) for (1), (2), (3), (5); SHELXL97 (Sheldrick, 1997), PARST (Nardelli, 1995) for (4).

Figures

(1)

Crystal data

C22H19NO	Z = 2
Mr = 313.38	F(000) = 332
Triclinic, P1	Dx = 1.258 Mg m^−3
a = 8.9727 (2) Å	Mo Kα radiation, λ = 0.71070 Å
b = 9.7552 (2) Å	Cell parameters from 6570 reflections
c = 10.0208 (2) Å	θ = 2.1–30.0°
α = 89.081 (1)°	µ = 0.08 mm^−1
β = 71.002 (1)°	T = 150 K
γ = 85.786 (1)°	Prismatic, colourless
V = 827.08 (3) Å^3	0.44 × 0.24 × 0.21 mm

Data collection

Nonius Kappa CCD diffractometer	3866 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
Graphite monochromator	θmax = 30.0°, θmin = 2.1°
ϕ scans and ω scans	h = −12→12
8302 measured reflections	k = −13→13
4703 independent reflections	l = −13→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: difference Fourier map
wR(F^2) = 0.120	All H-atom parameters refined
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0465P)^2 + 0.3404P] where P = (Fo^2 + 2Fc^2)/3
4703 reflections	(Δ/σ)max < 0.001
293 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.86704 (10)	0.31337 (9)	0.57519 (9)	0.02465 (19)
N1	0.70795 (12)	0.56089 (11)	0.64371 (10)	0.0226 (2)
H1	0.751 (2)	0.4797 (19)	0.6693 (18)	0.041 (5)*
C1	0.88411 (12)	0.34447 (12)	0.44935 (11)	0.0188 (2)
C2	0.82748 (13)	0.47367 (12)	0.40906 (12)	0.0197 (2)
C3	0.74166 (12)	0.57525 (11)	0.50419 (11)	0.0186 (2)
C4	0.68098 (13)	0.70106 (11)	0.44642 (11)	0.0189 (2)
C5	0.78670 (14)	0.78365 (12)	0.35190 (12)	0.0233 (2)
C6	0.72969 (16)	0.89627 (13)	0.29114 (13)	0.0289 (3)
C7	0.56801 (17)	0.92439 (14)	0.32142 (15)	0.0312 (3)
C8	0.46286 (16)	0.84256 (14)	0.41504 (15)	0.0310 (3)
C9	0.51865 (14)	0.73195 (13)	0.47848 (14)	0.0250 (2)
C10	0.96678 (13)	0.24023 (11)	0.33543 (12)	0.0190 (2)
C11	1.05476 (14)	0.12801 (12)	0.36745 (13)	0.0233 (2)
C12	1.13722 (16)	0.03165 (13)	0.26415 (14)	0.0286 (3)
C13	1.13332 (16)	0.04619 (13)	0.12746 (14)	0.0283 (3)
C14	1.04249 (16)	0.15522 (13)	0.09513 (13)	0.0269 (3)
C15	0.95918 (15)	0.25110 (12)	0.19855 (12)	0.0235 (2)
C16	0.63011 (14)	0.66414 (12)	0.75168 (12)	0.0220 (2)
C17	0.47476 (13)	0.62372 (12)	0.85496 (11)	0.0201 (2)
C18	0.40432 (14)	0.50602 (13)	0.83852 (13)	0.0242 (2)
C19	0.26322 (16)	0.47174 (14)	0.93883 (14)	0.0295 (3)
C20	0.19161 (15)	0.55559 (15)	1.05588 (14)	0.0310 (3)
C21	0.26097 (16)	0.67340 (14)	1.07303 (13)	0.0314 (3)
C22	0.40159 (15)	0.70736 (13)	0.97347 (13)	0.0264 (3)
H2	0.8423 (17)	0.4933 (15)	0.3075 (16)	0.026 (4)*
H5	0.9020 (19)	0.7632 (16)	0.3292 (16)	0.030 (4)*
H6	0.807 (2)	0.9580 (18)	0.2258 (18)	0.040 (4)*
H7	0.528 (2)	1.0031 (19)	0.2785 (19)	0.047 (5)*
H8	0.348 (2)	0.8638 (18)	0.4375 (18)	0.043 (5)*
H9	0.445 (2)	0.6744 (17)	0.5443 (18)	0.037 (4)*
H11	1.0589 (18)	0.1206 (16)	0.4640 (17)	0.029 (4)*
H12	1.198 (2)	−0.0489 (18)	0.2885 (18)	0.039 (4)*
H13	1.193 (2)	−0.0216 (19)	0.0540 (19)	0.044 (5)*
H14	1.0366 (19)	0.1649 (17)	−0.0009 (18)	0.036 (4)*
H15	0.8926 (18)	0.3247 (16)	0.1739 (16)	0.031 (4)*
H161	0.6138 (18)	0.7521 (16)	0.7048 (16)	0.029 (4)*
H162	0.7031 (18)	0.6818 (16)	0.8043 (16)	0.030 (4)*
H18	0.4557 (19)	0.4454 (17)	0.7561 (17)	0.034 (4)*
H19	0.217 (2)	0.3860 (19)	0.9245 (19)	0.044 (5)*
H20	0.090 (2)	0.5297 (18)	1.1277 (19)	0.044 (5)*
H21	0.211 (2)	0.7311 (18)	1.1604 (18)	0.039 (4)*
H22	0.455 (2)	0.7896 (17)	0.9882 (17)	0.037 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0271 (4)	0.0266 (4)	0.0182 (4)	0.0017 (3)	−0.0055 (3)	0.0023 (3)
N1	0.0246 (5)	0.0232 (5)	0.0162 (4)	0.0037 (4)	−0.0024 (4)	0.0004 (4)
C1	0.0156 (5)	0.0220 (5)	0.0178 (5)	−0.0022 (4)	−0.0038 (4)	0.0003 (4)
C2	0.0189 (5)	0.0210 (5)	0.0172 (5)	−0.0008 (4)	−0.0033 (4)	0.0007 (4)
C3	0.0154 (5)	0.0206 (5)	0.0184 (5)	−0.0027 (4)	−0.0033 (4)	0.0014 (4)
C4	0.0205 (5)	0.0192 (5)	0.0166 (5)	−0.0009 (4)	−0.0056 (4)	−0.0013 (4)
C5	0.0224 (6)	0.0256 (6)	0.0194 (5)	−0.0015 (4)	−0.0034 (4)	0.0008 (4)
C6	0.0356 (7)	0.0249 (6)	0.0232 (6)	−0.0020 (5)	−0.0057 (5)	0.0034 (5)
C7	0.0400 (7)	0.0243 (6)	0.0319 (7)	0.0048 (5)	−0.0166 (6)	0.0017 (5)
C8	0.0264 (6)	0.0289 (6)	0.0402 (7)	0.0030 (5)	−0.0154 (6)	−0.0013 (5)
C9	0.0210 (6)	0.0243 (6)	0.0295 (6)	−0.0018 (4)	−0.0078 (5)	0.0003 (5)
C10	0.0180 (5)	0.0185 (5)	0.0193 (5)	−0.0025 (4)	−0.0043 (4)	0.0009 (4)
C11	0.0262 (6)	0.0204 (5)	0.0246 (6)	−0.0004 (4)	−0.0104 (5)	0.0006 (4)
C12	0.0311 (6)	0.0214 (6)	0.0348 (7)	0.0045 (5)	−0.0141 (5)	−0.0026 (5)
C13	0.0303 (6)	0.0226 (6)	0.0291 (6)	0.0023 (5)	−0.0062 (5)	−0.0064 (5)
C14	0.0350 (7)	0.0237 (6)	0.0210 (6)	0.0000 (5)	−0.0079 (5)	−0.0017 (4)
C15	0.0280 (6)	0.0200 (5)	0.0219 (5)	0.0013 (4)	−0.0081 (5)	0.0001 (4)
C16	0.0236 (6)	0.0225 (6)	0.0172 (5)	−0.0003 (4)	−0.0030 (4)	−0.0020 (4)
C17	0.0207 (5)	0.0221 (5)	0.0164 (5)	0.0029 (4)	−0.0054 (4)	0.0010 (4)
C18	0.0252 (6)	0.0259 (6)	0.0213 (5)	0.0004 (5)	−0.0076 (5)	−0.0005 (4)
C19	0.0270 (6)	0.0324 (7)	0.0301 (6)	−0.0053 (5)	−0.0106 (5)	0.0075 (5)
C20	0.0230 (6)	0.0391 (7)	0.0261 (6)	0.0023 (5)	−0.0029 (5)	0.0111 (5)
C21	0.0311 (7)	0.0342 (7)	0.0206 (6)	0.0097 (5)	0.0002 (5)	0.0009 (5)
C22	0.0306 (6)	0.0235 (6)	0.0211 (6)	0.0034 (5)	−0.0039 (5)	−0.0022 (4)

Geometric parameters (Å, º)

O1—C1	1.2549 (14)	C11—H11	0.981 (16)
N1—C3	1.3380 (14)	C12—C13	1.3862 (19)
N1—C16	1.4535 (15)	C12—H12	0.997 (17)
N1—H1	0.924 (18)	C13—C14	1.3906 (18)
C1—C2	1.4257 (16)	C13—H13	0.987 (18)
C1—C10	1.5042 (15)	C14—C15	1.3898 (17)
C2—C3	1.3870 (15)	C14—H14	0.984 (17)
C2—H2	1.000 (15)	C15—H15	0.980 (16)
C3—C4	1.4907 (15)	C16—C17	1.5159 (16)
C4—C5	1.3960 (16)	C16—H161	0.996 (16)
C4—C9	1.3963 (16)	C16—H162	0.991 (16)
C5—C6	1.3922 (17)	C17—C18	1.3876 (17)
C5—H5	0.989 (16)	C17—C22	1.3970 (16)
C6—C7	1.389 (2)	C18—C19	1.3957 (18)
C6—H6	1.015 (18)	C18—H18	0.986 (16)
C7—C8	1.385 (2)	C19—C20	1.386 (2)
C7—H7	0.978 (19)	C19—H19	0.994 (19)
C8—C9	1.3874 (18)	C20—C21	1.385 (2)
C8—H8	0.990 (18)	C20—H20	1.008 (18)
C9—H9	0.974 (17)	C21—C22	1.3887 (18)
C10—C11	1.3968 (16)	C21—H21	1.004 (17)
C10—C15	1.3972 (16)	C22—H22	0.998 (17)
C11—C12	1.3904 (17)
C3—N1—C16	126.74 (10)	C13—C12—C11	120.19 (12)
C3—N1—H1	113.8 (11)	C13—C12—H12	119.8 (10)
C16—N1—H1	119.0 (11)	C11—C12—H12	120.0 (10)
O1—C1—C2	123.12 (10)	C12—C13—C14	119.69 (12)
O1—C1—C10	118.59 (10)	C12—C13—H13	120.1 (10)
C2—C1—C10	118.29 (10)	C14—C13—H13	120.2 (10)
C3—C2—C1	123.92 (10)	C15—C14—C13	120.14 (12)
C3—C2—H2	115.7 (9)	C15—C14—H14	119.6 (10)
C1—C2—H2	120.3 (9)	C13—C14—H14	120.3 (10)
N1—C3—C2	122.18 (10)	C14—C15—C10	120.65 (11)
N1—C3—C4	120.10 (10)	C14—C15—H15	118.4 (9)
C2—C3—C4	117.67 (10)	C10—C15—H15	120.9 (9)
C5—C4—C9	119.52 (11)	N1—C16—C17	114.02 (10)
C5—C4—C3	119.89 (10)	N1—C16—H161	108.8 (9)
C9—C4—C3	120.44 (10)	C17—C16—H161	110.3 (9)
C6—C5—C4	119.88 (11)	N1—C16—H162	108.2 (9)
C6—C5—H5	119.9 (9)	C17—C16—H162	109.1 (9)
C4—C5—H5	120.2 (9)	H161—C16—H162	106.2 (13)
C7—C6—C5	120.13 (12)	C18—C17—C22	118.77 (11)
C7—C6—H6	120.6 (10)	C18—C17—C16	122.91 (10)
C5—C6—H6	119.2 (10)	C22—C17—C16	118.30 (11)
C8—C7—C6	120.09 (12)	C17—C18—C19	120.55 (12)
C8—C7—H7	119.6 (11)	C17—C18—H18	119.5 (9)
C6—C7—H7	120.3 (11)	C19—C18—H18	119.9 (9)
C7—C8—C9	120.12 (12)	C20—C19—C18	120.16 (13)
C7—C8—H8	119.9 (10)	C20—C19—H19	121.4 (10)
C9—C8—H8	120.0 (10)	C18—C19—H19	118.4 (10)
C8—C9—C4	120.22 (12)	C21—C20—C19	119.68 (12)
C8—C9—H9	120.1 (10)	C21—C20—H20	120.9 (10)
C4—C9—H9	119.7 (10)	C19—C20—H20	119.5 (10)
C11—C10—C15	118.57 (11)	C20—C21—C22	120.19 (12)
C11—C10—C1	118.81 (10)	C20—C21—H21	119.0 (10)
C15—C10—C1	122.61 (10)	C22—C21—H21	120.7 (10)
C12—C11—C10	120.70 (11)	C21—C22—C17	120.65 (12)
C12—C11—H11	121.1 (9)	C21—C22—H22	120.3 (10)
C10—C11—H11	118.2 (9)	C17—C22—H22	119.0 (10)

(2)

Crystal data

C22H19NO2	Dx = 1.278 Mg m^−3
Mr = 329.38	Mo Kα radiation, λ = 0.71070 Å
Orthorhombic, Pbca	Cell parameters from 5680 reflections
a = 14.2380 (3) Å	θ = 2.4–28.0°
b = 14.3109 (3) Å	µ = 0.08 mm^−1
c = 16.8047 (3) Å	T = 150 K
V = 3424.1 (1) Å^3	Prismatic, colourless
Z = 8	0.32 × 0.31 × 0.25 mm
F(000) = 1392

Data collection

Nonius Kappa CCD diffractometer	3631 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 28.0°, θmin = 2.4°
ϕ scans and ω scans	h = −18→18
10220 measured reflections	k = −18→18
4138 independent reflections	l = −22→22

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: difference Fourier map
wR(F^2) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.35	w = 1/[σ^2(Fo^2) + (0.0297P)^2 + 2.1857P] where P = (Fo^2 + 2Fc^2)/3
4138 reflections	(Δ/σ)max < 0.001
303 parameters	Δρmax = 0.29 e Å^−3
1 restraint	Δρmin = −0.25 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.54034 (8)	−0.04592 (8)	0.73116 (7)	0.0257 (3)
O2	0.41750 (10)	0.27561 (10)	0.73947 (10)	0.0315 (4)	0.85
H2O	0.4223	0.3319	0.7474	0.038*	0.85
O2'	0.2117 (6)	0.0326 (5)	0.7951 (6)	0.032 (2)	0.15
H2O'	0.1578	0.0225	0.8100	0.039*	0.15
N1	0.44691 (11)	0.07649 (11)	0.82367 (9)	0.0246 (3)
C1	0.47903 (12)	−0.02864 (11)	0.67819 (10)	0.0222 (3)
C2	0.40712 (12)	0.03809 (12)	0.68964 (10)	0.0229 (4)
C3	0.39214 (11)	0.08646 (11)	0.76004 (10)	0.0208 (3)
C4	0.31176 (11)	0.15330 (12)	0.76378 (10)	0.0207 (3)
C5	0.32721 (12)	0.24889 (12)	0.75123 (11)	0.0242 (4)
H5	0.3890	0.2690	0.7448	0.051*	0.15
C6	0.25149 (14)	0.31008 (13)	0.75039 (12)	0.0303 (4)
C7	0.16096 (13)	0.27671 (13)	0.76168 (12)	0.0295 (4)
C8	0.14461 (13)	0.18264 (14)	0.77447 (11)	0.0276 (4)
C9	0.22050 (12)	0.12130 (12)	0.77586 (11)	0.0246 (4)
H9	0.2105	0.0585	0.7822	0.051*	0.85
C10	0.48313 (12)	−0.08049 (12)	0.60095 (10)	0.0237 (4)
C11	0.56855 (14)	−0.11721 (13)	0.57523 (11)	0.0277 (4)
C12	0.57367 (15)	−0.16606 (13)	0.50368 (12)	0.0317 (4)
C13	0.49408 (16)	−0.17958 (13)	0.45797 (12)	0.0332 (4)
C14	0.40900 (16)	−0.14304 (14)	0.48308 (12)	0.0350 (5)
C15	0.40350 (14)	−0.09361 (14)	0.55407 (12)	0.0309 (4)
C16	0.42715 (14)	0.11325 (13)	0.90262 (11)	0.0283 (4)
C17	0.38692 (12)	0.04006 (13)	0.95802 (11)	0.0260 (4)
C18	0.38016 (14)	0.05906 (15)	1.03945 (11)	0.0312 (4)
C19	0.34523 (14)	−0.00699 (17)	1.09142 (12)	0.0361 (5)
C20	0.31672 (14)	−0.09396 (16)	1.06416 (13)	0.0363 (5)
C21	0.32261 (15)	−0.11349 (15)	0.98348 (13)	0.0360 (5)
C22	0.35710 (14)	−0.04681 (14)	0.93092 (12)	0.0314 (4)
H1	0.4971 (16)	0.0341 (16)	0.8178 (14)	0.039 (6)*
H2	0.3654 (15)	0.0524 (14)	0.6467 (13)	0.027 (5)*
H6	0.2632 (17)	0.3763 (17)	0.7396 (14)	0.041 (6)*
H7	0.1081 (19)	0.3193 (18)	0.7620 (15)	0.050 (7)*
H8	0.0809 (17)	0.1598 (16)	0.7820 (13)	0.038 (6)*
H11	0.6258 (16)	−0.1051 (15)	0.6063 (13)	0.033 (6)*
H12	0.6335 (18)	−0.1907 (17)	0.4853 (15)	0.048 (7)*
H13	0.4995 (15)	−0.2167 (16)	0.4071 (14)	0.037 (6)*
H14	0.3512 (18)	−0.1527 (16)	0.4518 (14)	0.045 (7)*
H15	0.3390 (17)	−0.0685 (16)	0.5723 (14)	0.042 (6)*
H161	0.3847 (15)	0.1680 (15)	0.8965 (13)	0.032 (6)*
H162	0.4862 (17)	0.1383 (16)	0.9248 (14)	0.041 (6)*
H18	0.3994 (18)	0.1198 (19)	1.0585 (15)	0.054 (7)*
H19	0.3415 (17)	0.0063 (17)	1.1465 (15)	0.045 (6)*
H20	0.2952 (17)	−0.1416 (17)	1.1032 (15)	0.044 (7)*
H21	0.3030 (17)	−0.1753 (18)	0.9624 (15)	0.047 (7)*
H22	0.3627 (16)	−0.0623 (16)	0.8718 (14)	0.042 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0229 (6)	0.0232 (6)	0.0312 (7)	0.0035 (5)	−0.0028 (5)	−0.0027 (5)
O2	0.0194 (7)	0.0185 (7)	0.0566 (10)	−0.0030 (6)	0.0058 (7)	−0.0027 (7)
O2'	0.017 (4)	0.027 (4)	0.053 (6)	−0.001 (3)	0.008 (4)	0.007 (4)
N1	0.0237 (7)	0.0238 (7)	0.0262 (7)	0.0042 (6)	−0.0014 (6)	−0.0026 (6)
C1	0.0215 (8)	0.0186 (8)	0.0266 (8)	−0.0017 (6)	0.0029 (7)	0.0013 (7)
C2	0.0223 (8)	0.0226 (8)	0.0237 (8)	0.0015 (7)	0.0006 (7)	0.0012 (7)
C3	0.0190 (8)	0.0191 (7)	0.0243 (8)	−0.0016 (6)	0.0018 (6)	0.0011 (6)
C4	0.0197 (8)	0.0211 (8)	0.0213 (8)	0.0007 (6)	0.0008 (6)	−0.0027 (6)
C5	0.0203 (8)	0.0231 (8)	0.0294 (9)	−0.0017 (7)	0.0023 (7)	−0.0017 (7)
C6	0.0276 (9)	0.0209 (8)	0.0425 (10)	0.0026 (7)	0.0001 (9)	−0.0015 (8)
C7	0.0229 (9)	0.0301 (9)	0.0356 (10)	0.0071 (7)	−0.0016 (8)	−0.0057 (8)
C8	0.0199 (8)	0.0331 (10)	0.0299 (9)	−0.0011 (7)	0.0007 (7)	−0.0062 (8)
C9	0.0235 (8)	0.0226 (8)	0.0276 (9)	−0.0010 (7)	0.0019 (7)	−0.0027 (7)
C10	0.0267 (9)	0.0184 (8)	0.0261 (9)	0.0006 (7)	0.0038 (7)	−0.0003 (7)
C11	0.0285 (9)	0.0243 (9)	0.0304 (9)	0.0021 (7)	0.0041 (8)	−0.0009 (7)
C12	0.0350 (10)	0.0279 (9)	0.0321 (10)	0.0041 (8)	0.0107 (8)	−0.0004 (8)
C13	0.0479 (12)	0.0254 (9)	0.0264 (9)	0.0009 (8)	0.0048 (9)	−0.0023 (8)
C14	0.0381 (11)	0.0328 (10)	0.0340 (11)	0.0015 (9)	−0.0053 (9)	−0.0074 (8)
C15	0.0291 (10)	0.0294 (9)	0.0340 (10)	0.0032 (8)	0.0004 (8)	−0.0045 (8)
C16	0.0311 (10)	0.0268 (9)	0.0269 (9)	0.0034 (8)	−0.0042 (8)	−0.0063 (7)
C17	0.0196 (8)	0.0314 (9)	0.0270 (9)	0.0066 (7)	−0.0038 (7)	−0.0029 (7)
C18	0.0286 (10)	0.0372 (11)	0.0278 (9)	0.0058 (8)	−0.0039 (8)	−0.0077 (8)
C19	0.0304 (10)	0.0529 (13)	0.0249 (9)	0.0082 (9)	−0.0002 (8)	−0.0021 (9)
C20	0.0296 (10)	0.0445 (12)	0.0350 (11)	0.0040 (9)	0.0017 (8)	0.0068 (9)
C21	0.0334 (10)	0.0361 (11)	0.0384 (11)	−0.0007 (9)	0.0004 (9)	−0.0013 (9)
C22	0.0318 (10)	0.0337 (10)	0.0287 (9)	0.0010 (8)	−0.0010 (8)	−0.0041 (8)

Geometric parameters (Å, º)

O1—C1	1.271 (2)	C10—C15	1.393 (3)
O2—C5	1.356 (2)	C10—C11	1.394 (3)
O2—H2O	0.8200	C11—C12	1.393 (3)
O2—H5	0.4265 (14)	C11—H11	0.98 (2)
O2'—C9	1.316 (7)	C12—C13	1.383 (3)
O2'—H2O'	0.8200	C12—H12	0.97 (3)
O2'—H9	0.430 (7)	C13—C14	1.385 (3)
N1—C3	1.331 (2)	C13—H13	1.01 (2)
N1—C16	1.455 (2)	C14—C15	1.389 (3)
N1—H1	0.94 (2)	C14—H14	0.99 (3)
C1—C2	1.413 (2)	C15—H15	1.03 (2)
C1—C10	1.496 (2)	C16—C17	1.514 (3)
C2—C3	1.387 (2)	C16—H161	0.99 (2)
C2—H2	0.96 (2)	C16—H162	0.99 (2)
C3—C4	1.493 (2)	C17—C22	1.390 (3)
C4—C9	1.393 (2)	C17—C18	1.398 (3)
C4—C5	1.402 (2)	C18—C19	1.380 (3)
C5—C6	1.389 (2)	C18—H18	0.97 (3)
C5—H5	0.9315 (17)	C19—C20	1.387 (3)
C6—C7	1.388 (3)	C19—H19	0.95 (3)
C6—H6	0.98 (2)	C20—C21	1.387 (3)
C7—C8	1.383 (3)	C20—H20	0.99 (2)
C7—H7	0.97 (3)	C21—C22	1.390 (3)
C8—C9	1.392 (3)	C21—H21	0.99 (3)
C8—H8	0.97 (2)	C22—H22	1.02 (2)
C9—H9	0.9157 (17)
C5—O2—H2O	109.5	C15—C10—C11	118.94 (17)
C5—O2—H5	4.99 (17)	C15—C10—C1	121.71 (16)
H2O—O2—H5	105.4	C11—C10—C1	119.35 (16)
C9—O2'—H2O'	109.5	C12—C11—C10	120.18 (18)
C9—O2'—H9	17.7 (9)	C12—C11—H11	120.2 (13)
H2O'—O2'—H9	105.5	C10—C11—H11	119.5 (13)
C3—N1—C16	125.49 (15)	C13—C12—C11	120.46 (18)
C3—N1—H1	115.4 (14)	C13—C12—H12	119.4 (15)
C16—N1—H1	118.4 (14)	C11—C12—H12	120.1 (15)
O1—C1—C2	122.25 (16)	C12—C13—C14	119.65 (18)
O1—C1—C10	118.97 (15)	C12—C13—H13	118.7 (13)
C2—C1—C10	118.78 (15)	C14—C13—H13	121.6 (13)
C3—C2—C1	124.38 (16)	C13—C14—C15	120.21 (19)
C3—C2—H2	116.2 (12)	C13—C14—H14	121.0 (14)
C1—C2—H2	119.4 (12)	C15—C14—H14	118.8 (14)
N1—C3—C2	122.78 (16)	C14—C15—C10	120.55 (18)
N1—C3—C4	118.95 (15)	C14—C15—H15	118.8 (13)
C2—C3—C4	118.26 (15)	C10—C15—H15	120.6 (13)
C9—C4—C5	119.30 (15)	N1—C16—C17	112.56 (15)
C9—C4—C3	120.71 (15)	N1—C16—H161	107.9 (12)
C5—C4—C3	119.92 (15)	C17—C16—H161	112.2 (12)
O2—C5—C6	123.83 (17)	N1—C16—H162	108.1 (14)
O2—C5—C4	116.49 (15)	C17—C16—H162	110.0 (14)
C6—C5—C4	119.67 (16)	H161—C16—H162	105.7 (18)
O2—C5—H5	2.28 (8)	C22—C17—C18	118.25 (18)
C6—C5—H5	122.51 (18)	C22—C17—C16	122.20 (17)
C4—C5—H5	117.80 (17)	C18—C17—C16	119.55 (17)
C7—C6—C5	120.18 (17)	C19—C18—C17	120.73 (19)
C7—C6—H6	121.1 (14)	C19—C18—H18	120.6 (16)
C5—C6—H6	118.7 (14)	C17—C18—H18	118.7 (16)
C8—C7—C6	120.83 (17)	C18—C19—C20	120.74 (19)
C8—C7—H7	118.7 (15)	C18—C19—H19	120.1 (15)
C6—C7—H7	120.4 (15)	C20—C19—H19	119.1 (15)
C7—C8—C9	119.06 (17)	C21—C20—C19	119.1 (2)
C7—C8—H8	120.3 (14)	C21—C20—H20	121.7 (14)
C9—C8—H8	120.6 (14)	C19—C20—H20	119.2 (14)
O2'—C9—C8	122.6 (4)	C20—C21—C22	120.3 (2)
O2'—C9—C4	116.2 (4)	C20—C21—H21	120.8 (15)
C8—C9—C4	120.95 (16)	C22—C21—H21	119.0 (15)
O2'—C9—H9	8.2 (4)	C21—C22—C17	120.91 (19)
C8—C9—H9	119.94 (18)	C21—C22—H22	119.8 (13)
C4—C9—H9	119.03 (17)	C17—C22—H22	119.2 (13)

(3)

Crystal data

C23H20N2O4	Z = 2
Mr = 388.41	F(000) = 408
Triclinic, P1	Dx = 1.346 Mg m^−3
a = 6.9599 (2) Å	Mo Kα radiation, λ = 0.71070 Å
b = 8.4786 (3) Å	Cell parameters from 6532 reflections
c = 17.1616 (6) Å	θ = 2.4–27.5°
α = 82.282 (2)°	µ = 0.09 mm^−1
β = 78.773 (2)°	T = 150 K
γ = 75.599 (2)°	Plate, colourless
V = 958.18 (6) Å^3	0.35 × 0.33 × 0.09 mm

Data collection

Nonius Kappa CCD diffractometer	3563 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Graphite monochromator	θmax = 27.5°, θmin = 2.4°
ϕ scans and ω scans	h = −9→9
8934 measured reflections	k = −10→11
4331 independent reflections	l = −21→22

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: difference Fourier map
wR(F^2) = 0.123	All H-atom parameters refined
S = 1.19	w = 1/[σ^2(Fo^2) + (0.033P)^2 + 0.5384P] where P = (Fo^2 + 2Fc^2)/3
4331 reflections	(Δ/σ)max < 0.001
342 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	−0.07927 (19)	−0.26221 (15)	0.25074 (7)	0.0285 (3)
O2	0.59333 (19)	0.44447 (15)	0.25503 (8)	0.0312 (3)
O3	−0.1854 (2)	−0.76039 (17)	0.42083 (9)	0.0433 (4)
O4	−0.3032 (2)	−0.74710 (18)	0.54671 (9)	0.0413 (4)
N1	0.1250 (3)	−0.0516 (2)	0.16791 (9)	0.0301 (4)
H1	0.050 (4)	−0.130 (3)	0.1715 (14)	0.046 (7)*
N2	−0.2412 (2)	−0.68586 (19)	0.48049 (10)	0.0307 (4)
C1	−0.0588 (2)	−0.2069 (2)	0.31224 (10)	0.0225 (4)
C2	0.0472 (3)	−0.0831 (2)	0.30992 (10)	0.0230 (4)
C3	0.1366 (3)	−0.0112 (2)	0.23929 (10)	0.0228 (4)
C4	0.2527 (3)	0.1128 (2)	0.24327 (10)	0.0229 (4)
C5	0.4392 (3)	0.0636 (2)	0.26846 (11)	0.0254 (4)
C6	0.5489 (3)	0.1769 (2)	0.27208 (11)	0.0260 (4)
C7	0.4724 (2)	0.3420 (2)	0.25119 (10)	0.0222 (4)
C8	0.2841 (3)	0.3932 (2)	0.22876 (10)	0.0249 (4)
C9	0.1758 (3)	0.2778 (2)	0.22464 (11)	0.0270 (4)
C10	−0.1451 (2)	−0.2801 (2)	0.39210 (10)	0.0222 (4)
C11	−0.1631 (3)	−0.4418 (2)	0.39848 (11)	0.0232 (4)
C12	−0.2333 (3)	−0.5120 (2)	0.47281 (11)	0.0256 (4)
C13	−0.2922 (3)	−0.4272 (2)	0.53998 (11)	0.0298 (4)
C14	−0.2792 (3)	−0.2654 (3)	0.53250 (12)	0.0324 (4)
C15	−0.2049 (3)	−0.1920 (2)	0.45913 (11)	0.0268 (4)
C16	0.2143 (3)	0.0152 (2)	0.09051 (11)	0.0304 (4)
C17	0.0695 (3)	0.1487 (2)	0.04892 (10)	0.0281 (4)
C18	0.1380 (3)	0.2176 (2)	−0.02653 (11)	0.0345 (4)
C19	0.0112 (4)	0.3405 (3)	−0.06614 (12)	0.0409 (5)
C20	−0.1854 (4)	0.3961 (3)	−0.03122 (13)	0.0461 (6)
C21	−0.2554 (4)	0.3277 (3)	0.04312 (14)	0.0494 (6)
C22	−0.1286 (3)	0.2039 (3)	0.08310 (12)	0.0388 (5)
C23	0.5207 (3)	0.6140 (2)	0.23199 (15)	0.0365 (5)
H2	0.061 (3)	−0.048 (2)	0.3574 (11)	0.022 (5)*
H5	0.493 (3)	−0.050 (3)	0.2833 (12)	0.029 (5)*
H6	0.674 (3)	0.144 (3)	0.2901 (12)	0.036 (6)*
H8	0.225 (3)	0.511 (3)	0.2161 (12)	0.033 (5)*
H9	0.044 (3)	0.315 (3)	0.2096 (13)	0.039 (6)*
H11	−0.122 (3)	−0.505 (2)	0.3532 (12)	0.027 (5)*
H13	−0.343 (3)	−0.478 (3)	0.5898 (13)	0.037 (6)*
H14	−0.319 (3)	−0.206 (3)	0.5788 (13)	0.036 (6)*
H15	−0.200 (3)	−0.080 (3)	0.4544 (11)	0.026 (5)*
H161	0.329 (3)	0.058 (3)	0.0985 (13)	0.039 (6)*
H162	0.270 (3)	−0.077 (3)	0.0560 (13)	0.036 (6)*
H18	0.277 (4)	0.178 (3)	−0.0496 (13)	0.040 (6)*
H19	0.060 (4)	0.395 (3)	−0.1189 (15)	0.051 (7)*
H20	−0.274 (4)	0.483 (3)	−0.0582 (14)	0.050 (7)*
H21	−0.392 (5)	0.365 (4)	0.0677 (17)	0.073 (9)*
H22	−0.181 (3)	0.154 (3)	0.1364 (14)	0.046 (6)*
H231	0.629 (3)	0.666 (3)	0.2375 (12)	0.034 (5)*
H232	0.492 (4)	0.631 (3)	0.1757 (15)	0.049 (7)*
H233	0.393 (4)	0.662 (3)	0.2686 (14)	0.050 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0344 (7)	0.0299 (7)	0.0254 (6)	−0.0137 (5)	−0.0076 (5)	−0.0016 (5)
O2	0.0270 (7)	0.0253 (7)	0.0439 (8)	−0.0093 (5)	−0.0087 (6)	−0.0023 (6)
O3	0.0569 (10)	0.0270 (7)	0.0478 (9)	−0.0153 (7)	−0.0056 (7)	−0.0033 (7)
O4	0.0450 (9)	0.0400 (8)	0.0418 (8)	−0.0212 (7)	−0.0140 (7)	0.0178 (7)
N1	0.0412 (9)	0.0301 (8)	0.0225 (8)	−0.0163 (7)	−0.0063 (6)	0.0023 (6)
N2	0.0283 (8)	0.0279 (8)	0.0382 (9)	−0.0112 (7)	−0.0122 (7)	0.0080 (7)
C1	0.0206 (8)	0.0208 (8)	0.0246 (8)	−0.0029 (7)	−0.0046 (6)	0.0004 (7)
C2	0.0258 (9)	0.0225 (8)	0.0219 (8)	−0.0067 (7)	−0.0064 (7)	−0.0003 (7)
C3	0.0228 (8)	0.0200 (8)	0.0251 (8)	−0.0036 (7)	−0.0059 (7)	0.0002 (7)
C4	0.0240 (9)	0.0234 (9)	0.0214 (8)	−0.0077 (7)	−0.0023 (6)	−0.0005 (7)
C5	0.0261 (9)	0.0202 (9)	0.0289 (9)	−0.0031 (7)	−0.0059 (7)	−0.0011 (7)
C6	0.0216 (9)	0.0274 (9)	0.0288 (9)	−0.0037 (7)	−0.0060 (7)	−0.0031 (7)
C7	0.0229 (8)	0.0236 (8)	0.0207 (8)	−0.0085 (7)	−0.0003 (6)	−0.0035 (6)
C8	0.0264 (9)	0.0198 (9)	0.0271 (9)	−0.0048 (7)	−0.0044 (7)	0.0017 (7)
C9	0.0234 (9)	0.0252 (9)	0.0326 (9)	−0.0063 (7)	−0.0078 (7)	0.0024 (7)
C10	0.0189 (8)	0.0227 (8)	0.0256 (8)	−0.0058 (7)	−0.0056 (6)	0.0007 (7)
C11	0.0202 (8)	0.0244 (9)	0.0257 (9)	−0.0055 (7)	−0.0057 (7)	−0.0011 (7)
C12	0.0221 (8)	0.0250 (9)	0.0313 (9)	−0.0091 (7)	−0.0083 (7)	0.0041 (7)
C13	0.0254 (9)	0.0401 (11)	0.0251 (9)	−0.0135 (8)	−0.0035 (7)	0.0037 (8)
C14	0.0316 (10)	0.0392 (11)	0.0277 (9)	−0.0128 (8)	0.0017 (8)	−0.0080 (8)
C15	0.0262 (9)	0.0254 (9)	0.0300 (9)	−0.0087 (7)	−0.0031 (7)	−0.0040 (7)
C16	0.0346 (10)	0.0316 (10)	0.0236 (9)	−0.0089 (8)	−0.0007 (8)	−0.0008 (8)
C17	0.0365 (10)	0.0275 (9)	0.0227 (9)	−0.0108 (8)	−0.0046 (7)	−0.0044 (7)
C18	0.0409 (12)	0.0350 (11)	0.0271 (10)	−0.0115 (9)	−0.0021 (8)	−0.0012 (8)
C19	0.0616 (14)	0.0362 (11)	0.0256 (10)	−0.0122 (10)	−0.0106 (9)	0.0016 (8)
C20	0.0579 (15)	0.0429 (12)	0.0341 (11)	0.0038 (11)	−0.0184 (10)	−0.0053 (9)
C21	0.0405 (13)	0.0638 (16)	0.0369 (12)	0.0037 (11)	−0.0060 (10)	−0.0106 (11)
C22	0.0379 (11)	0.0486 (13)	0.0256 (10)	−0.0054 (9)	−0.0011 (8)	−0.0035 (9)
C23	0.0346 (11)	0.0251 (10)	0.0526 (13)	−0.0126 (8)	−0.0080 (10)	−0.0014 (9)

Geometric parameters (Å, º)

O1—C1	1.256 (2)	C11—C12	1.385 (2)
O2—C7	1.367 (2)	C11—H11	0.96 (2)
O2—C23	1.429 (2)	C12—C13	1.380 (3)
O3—N2	1.223 (2)	C13—C14	1.384 (3)
O4—N2	1.228 (2)	C13—H13	0.95 (2)
N1—C3	1.338 (2)	C14—C15	1.391 (3)
N1—C16	1.457 (2)	C14—H14	0.96 (2)
N1—H1	0.93 (2)	C15—H15	0.95 (2)
N2—C12	1.476 (2)	C16—C17	1.517 (3)
C1—C2	1.418 (2)	C16—H161	0.99 (2)
C1—C10	1.504 (2)	C16—H162	1.00 (2)
C2—C3	1.387 (2)	C17—C22	1.379 (3)
C2—H2	0.933 (19)	C17—C18	1.393 (3)
C3—C4	1.492 (2)	C18—C19	1.383 (3)
C4—C9	1.386 (2)	C18—H18	0.97 (2)
C4—C5	1.395 (2)	C19—C20	1.375 (3)
C5—C6	1.382 (3)	C19—H19	1.00 (2)
C5—H5	0.96 (2)	C20—C21	1.379 (3)
C6—C7	1.393 (2)	C20—H20	0.96 (3)
C6—H6	0.95 (2)	C21—C22	1.391 (3)
C7—C8	1.387 (2)	C21—H21	0.95 (3)
C8—C9	1.392 (3)	C22—H22	1.00 (2)
C8—H8	0.99 (2)	C23—H231	0.99 (2)
C9—H9	0.96 (2)	C23—H232	1.01 (2)
C10—C15	1.394 (2)	C23—H233	1.01 (3)
C10—C11	1.395 (2)
C7—O2—C23	116.93 (14)	C13—C12—N2	118.83 (16)
C3—N1—C16	126.46 (16)	C11—C12—N2	118.34 (16)
C3—N1—H1	112.7 (14)	C12—C13—C14	118.35 (17)
C16—N1—H1	120.8 (14)	C12—C13—H13	120.6 (13)
O3—N2—O4	123.93 (16)	C14—C13—H13	121.1 (13)
O3—N2—C12	118.23 (15)	C13—C14—C15	120.40 (18)
O4—N2—C12	117.84 (16)	C13—C14—H14	119.0 (13)
O1—C1—C2	123.18 (15)	C15—C14—H14	120.6 (13)
O1—C1—C10	118.15 (15)	C14—C15—C10	120.32 (17)
C2—C1—C10	118.64 (15)	C14—C15—H15	119.6 (12)
C3—C2—C1	122.90 (16)	C10—C15—H15	120.1 (12)
C3—C2—H2	117.3 (11)	N1—C16—C17	114.42 (16)
C1—C2—H2	119.8 (11)	N1—C16—H161	107.9 (12)
N1—C3—C2	122.10 (16)	C17—C16—H161	109.7 (13)
N1—C3—C4	119.06 (15)	N1—C16—H162	107.8 (12)
C2—C3—C4	118.83 (15)	C17—C16—H162	109.2 (12)
C9—C4—C5	118.98 (16)	H161—C16—H162	107.6 (18)
C9—C4—C3	121.07 (15)	C22—C17—C18	118.68 (18)
C5—C4—C3	119.92 (15)	C22—C17—C16	122.22 (17)
C6—C5—C4	120.56 (16)	C18—C17—C16	119.10 (17)
C6—C5—H5	119.2 (12)	C19—C18—C17	120.9 (2)
C4—C5—H5	120.2 (12)	C19—C18—H18	121.5 (13)
C5—C6—C7	119.93 (16)	C17—C18—H18	117.6 (13)
C5—C6—H6	120.6 (13)	C20—C19—C18	120.1 (2)
C7—C6—H6	119.5 (13)	C20—C19—H19	118.2 (14)
O2—C7—C8	124.15 (15)	C18—C19—H19	121.7 (14)
O2—C7—C6	115.76 (15)	C19—C20—C21	119.6 (2)
C8—C7—C6	120.09 (16)	C19—C20—H20	120.4 (15)
C7—C8—C9	119.45 (16)	C21—C20—H20	120.1 (15)
C7—C8—H8	120.9 (12)	C20—C21—C22	120.6 (2)
C9—C8—H8	119.7 (12)	C20—C21—H21	120.3 (18)
C4—C9—C8	120.93 (16)	C22—C21—H21	119.2 (18)
C4—C9—H9	120.4 (13)	C17—C22—C21	120.2 (2)
C8—C9—H9	118.6 (13)	C17—C22—H22	119.9 (13)
C15—C10—C11	119.73 (16)	C21—C22—H22	119.9 (13)
C15—C10—C1	122.03 (15)	O2—C23—H231	104.7 (12)
C11—C10—C1	118.24 (15)	O2—C23—H232	110.8 (14)
C12—C11—C10	118.33 (17)	H231—C23—H232	112.2 (18)
C12—C11—H11	120.6 (12)	O2—C23—H233	111.4 (14)
C10—C11—H11	121.0 (12)	H231—C23—H233	109.4 (18)
C13—C12—C11	122.81 (16)	H232—C23—H233	108.3 (19)

(4)

Crystal data

C15H17NO3	Z = 2
Mr = 259.30	F(000) = 276
Triclinic, P1	Dx = 1.356 Mg m^−3
a = 7.7200 (2) Å	Mo Kα radiation, λ = 0.71070 Å
b = 8.9566 (3) Å	Cell parameters from 3546 reflections
c = 9.5777 (3) Å	θ = 2.1–27.6°
α = 93.830 (2)°	µ = 0.10 mm^−1
β = 92.083 (2)°	T = 150 K
γ = 105.755 (2)°	Prismatic, colourless
V = 634.92 (3) Å^3	0.50 × 0.38 × 0.17 mm

Data collection

Nonius Kappa CCD diffractometer	2554 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
Graphite monochromator	θmax = 27.6°, θmin = 2.1°
ϕ scans and ω scans	h = −10→10
5780 measured reflections	k = −11→10
2862 independent reflections	l = −12→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.052	Hydrogen site location: difference Fourier map
wR(F^2) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0714P)^2 + 0.3622P] where P = (Fo^2 + 2Fc^2)/3
2862 reflections	(Δ/σ)max = 0.001
232 parameters	Δρmax = 0.46 e Å^−3
0 restraints	Δρmin = −0.48 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.19912 (18)	−0.09362 (15)	0.69426 (13)	0.0220 (3)
O1	−0.04487 (15)	0.03678 (14)	0.75874 (13)	0.0303 (3)
O2	0.54338 (15)	0.26310 (14)	0.96344 (13)	0.0326 (3)
O3	0.24888 (15)	−0.64251 (12)	0.41206 (11)	0.0257 (3)
C1	0.0674 (2)	0.12695 (17)	0.84509 (16)	0.0220 (3)
C2	0.25460 (19)	0.12764 (16)	0.85821 (14)	0.0189 (3)
C3	0.31676 (19)	0.01395 (16)	0.77808 (15)	0.0192 (3)
C4	−0.0018 (3)	0.2369 (2)	0.9397 (2)	0.0372 (4)
H41	0.003 (3)	0.303 (3)	0.886 (3)	0.045*
H42	−0.129 (3)	0.235 (3)	0.906 (2)	0.045*
C5	0.1024 (6)	0.2972 (7)	1.0637 (5)	0.0250 (15)	0.387 (9)
H51A	0.0670	0.2220	1.1329	0.030*	0.387 (9)
H52A	0.0705	0.3903	1.0974	0.030*	0.387 (9)
C5'	0.1380 (4)	0.3717 (4)	1.0111 (4)	0.0306 (10)	0.613 (9)
H51B	0.1695	0.4527	0.9467	0.037*	0.613 (9)
H52B	0.0862	0.4128	1.0907	0.037*	0.613 (9)
C6	0.3004 (2)	0.3374 (2)	1.0597 (2)	0.0409 (5)
H61	0.3494	0.3296	1.1528	0.049*
H62	0.3427	0.4455	1.0393	0.049*
C7	0.3791 (2)	0.24258 (17)	0.95721 (16)	0.0224 (3)
C8	0.5094 (2)	0.0108 (2)	0.78224 (19)	0.0266 (4)
C9	0.22696 (19)	−0.23087 (17)	0.62421 (15)	0.0207 (3)
C10	0.1934 (2)	−0.25666 (17)	0.47952 (16)	0.0222 (3)
C11	0.2049 (2)	−0.39440 (18)	0.41204 (15)	0.0227 (3)
C12	0.24852 (19)	−0.50817 (17)	0.48801 (15)	0.0201 (3)
C13	0.2865 (2)	−0.48082 (18)	0.63190 (16)	0.0225 (3)
C14	0.2739 (2)	−0.34210 (18)	0.69991 (15)	0.0227 (3)
C15	0.2800 (2)	−0.76576 (18)	0.48763 (18)	0.0256 (3)
H1	0.085 (3)	−0.079 (2)	0.691 (2)	0.035 (5)*
H81	0.583 (3)	0.110 (3)	0.758 (2)	0.042 (6)*
H82	0.521 (3)	−0.075 (3)	0.718 (2)	0.046 (6)*
H83	0.553 (3)	−0.005 (3)	0.879 (3)	0.045 (6)*
H10	0.160 (3)	−0.176 (2)	0.428 (2)	0.027 (5)*
H11	0.183 (3)	−0.413 (2)	0.309 (2)	0.036 (5)*
H13	0.320 (3)	−0.558 (3)	0.683 (2)	0.038 (5)*
H14	0.295 (3)	−0.324 (2)	0.800 (2)	0.028 (5)*
H151	0.189 (3)	−0.791 (2)	0.558 (2)	0.033 (5)*
H152	0.263 (3)	−0.853 (2)	0.415 (2)	0.035 (5)*
H153	0.405 (3)	−0.733 (2)	0.529 (2)	0.035 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0214 (6)	0.0217 (6)	0.0231 (6)	0.0083 (5)	−0.0015 (5)	−0.0059 (5)
O1	0.0231 (6)	0.0313 (6)	0.0361 (6)	0.0115 (5)	−0.0081 (5)	−0.0118 (5)
O2	0.0225 (6)	0.0332 (6)	0.0394 (7)	0.0076 (5)	−0.0065 (5)	−0.0125 (5)
O3	0.0336 (6)	0.0226 (5)	0.0212 (5)	0.0103 (5)	0.0007 (4)	−0.0061 (4)
C1	0.0224 (7)	0.0202 (7)	0.0236 (7)	0.0073 (6)	−0.0001 (6)	−0.0022 (5)
C2	0.0205 (7)	0.0180 (7)	0.0183 (7)	0.0061 (5)	0.0008 (5)	−0.0003 (5)
C3	0.0210 (7)	0.0182 (6)	0.0181 (7)	0.0049 (5)	0.0018 (5)	0.0013 (5)
C4	0.0274 (9)	0.0372 (10)	0.0475 (11)	0.0152 (8)	−0.0027 (8)	−0.0170 (8)
C5	0.028 (2)	0.023 (3)	0.023 (2)	0.0066 (18)	0.0070 (16)	−0.0036 (19)
C5'	0.0336 (16)	0.0264 (18)	0.0332 (17)	0.0128 (13)	0.0039 (12)	−0.0077 (15)
C6	0.0314 (9)	0.0462 (11)	0.0405 (10)	0.0107 (8)	−0.0035 (8)	−0.0261 (8)
C7	0.0239 (7)	0.0201 (7)	0.0228 (7)	0.0065 (6)	−0.0003 (6)	−0.0016 (5)
C8	0.0201 (7)	0.0251 (8)	0.0335 (9)	0.0061 (6)	0.0034 (6)	−0.0064 (6)
C9	0.0190 (7)	0.0199 (7)	0.0219 (7)	0.0047 (5)	0.0011 (5)	−0.0046 (5)
C10	0.0213 (7)	0.0228 (7)	0.0222 (7)	0.0061 (6)	−0.0004 (5)	0.0003 (6)
C11	0.0244 (7)	0.0256 (7)	0.0170 (7)	0.0064 (6)	−0.0001 (5)	−0.0030 (5)
C12	0.0181 (7)	0.0199 (7)	0.0207 (7)	0.0040 (5)	0.0020 (5)	−0.0044 (5)
C13	0.0250 (7)	0.0219 (7)	0.0208 (7)	0.0078 (6)	−0.0009 (6)	−0.0012 (5)
C14	0.0259 (7)	0.0239 (7)	0.0175 (7)	0.0072 (6)	−0.0010 (5)	−0.0033 (5)
C15	0.0264 (8)	0.0208 (7)	0.0297 (8)	0.0081 (6)	0.0016 (6)	−0.0034 (6)

Geometric parameters (Å, º)

N1—C3	1.3290 (19)	C5'—H51B	0.9700
N1—C9	1.4322 (18)	C5'—H52B	0.9700
N1—H1	0.93 (2)	C6—C7	1.505 (2)
O1—C1	1.2514 (19)	C6—H61	0.9700
O2—C7	1.2299 (19)	C6—H62	0.9700
O3—C12	1.3645 (17)	C8—H81	0.97 (2)
O3—C15	1.4278 (19)	C8—H82	0.98 (2)
C1—C2	1.444 (2)	C8—H83	1.00 (2)
C1—C4	1.509 (2)	C9—C14	1.387 (2)
C2—C3	1.4297 (19)	C9—C10	1.393 (2)
C2—C7	1.466 (2)	C10—C11	1.380 (2)
C3—C8	1.494 (2)	C10—H10	0.99 (2)
C4—C5	1.399 (5)	C11—C12	1.396 (2)
C4—C5'	1.489 (4)	C11—H11	0.99 (2)
C4—H41	0.80 (3)	C12—C13	1.390 (2)
C4—H42	1.01 (2)	C13—C14	1.393 (2)
C5—C6	1.475 (5)	C13—H13	0.96 (2)
C5—H51A	0.9700	C14—H14	0.96 (2)
C5—H52A	0.9700	C15—H151	0.98 (2)
C5'—C6	1.438 (4)	C15—H152	0.99 (2)
C5'—H41	1.54 (3)	C15—H153	0.99 (2)
C3—N1—C9	127.39 (13)	C5—C6—C7	117.7 (2)
C3—N1—H1	112.8 (13)	C5'—C6—H61	132.3
C9—N1—H1	119.5 (13)	C5—C6—H61	107.9
C12—O3—C15	117.27 (12)	C7—C6—H61	107.9
O1—C1—C2	123.16 (13)	C5'—C6—H62	77.0
O1—C1—C4	116.80 (14)	C5—C6—H62	107.9
C2—C1—C4	120.03 (14)	C7—C6—H62	107.9
C3—C2—C1	120.13 (13)	H61—C6—H62	107.2
C3—C2—C7	120.25 (13)	O2—C7—C2	123.72 (14)
C1—C2—C7	119.59 (13)	O2—C7—C6	118.29 (14)
N1—C3—C2	118.98 (13)	C2—C7—C6	117.97 (14)
N1—C3—C8	117.84 (13)	C3—C8—H81	108.7 (13)
C2—C3—C8	123.17 (13)	C3—C8—H82	109.2 (14)
C5—C4—C5'	34.2 (2)	H81—C8—H82	111.8 (19)
C5—C4—C1	116.1 (2)	C3—C8—H83	111.6 (13)
C5'—C4—C1	115.81 (17)	H81—C8—H83	107.0 (18)
C5—C4—H41	111.7 (19)	H82—C8—H83	108.6 (19)
C5'—C4—H41	78.2 (18)	C14—C9—C10	120.20 (13)
C1—C4—H41	97.4 (18)	C14—C9—N1	120.68 (13)
C5—C4—H42	132.9 (13)	C10—C9—N1	118.96 (13)
C5'—C4—H42	126.9 (13)	C11—C10—C9	119.65 (14)
C1—C4—H42	109.9 (13)	C11—C10—H10	121.6 (11)
H41—C4—H42	70 (2)	C9—C10—H10	118.7 (11)
C4—C5—C6	118.4 (3)	C10—C11—C12	120.42 (13)
C4—C5—H51A	107.7	C10—C11—H11	120.1 (12)
C6—C5—H51A	107.7	C12—C11—H11	119.5 (12)
C4—C5—H52A	107.7	O3—C12—C13	124.37 (14)
C6—C5—H52A	107.7	O3—C12—C11	115.70 (13)
H51A—C5—H52A	107.1	C13—C12—C11	119.92 (13)
C6—C5'—C4	115.0 (2)	C12—C13—C14	119.52 (14)
C6—C5'—H41	132.1 (10)	C12—C13—H13	119.9 (13)
C4—C5'—H41	30.6 (9)	C14—C13—H13	120.6 (13)
C6—C5'—H51B	108.5	C9—C14—C13	120.23 (14)
C4—C5'—H51B	108.5	C9—C14—H14	119.8 (12)
H41—C5'—H51B	78.3	C13—C14—H14	120.0 (12)
C6—C5'—H52B	108.5	O3—C15—H151	108.3 (12)
C4—C5'—H52B	108.5	O3—C15—H152	103.9 (12)
H41—C5'—H52B	114.3	H151—C15—H152	111.0 (17)
H51B—C5'—H52B	107.5	O3—C15—H153	108.9 (12)
C5'—C6—C5	34.1 (2)	H151—C15—H153	113.1 (17)
C5'—C6—C7	115.94 (18)	H152—C15—H153	111.3 (17)

(5)

Crystal data

C15H17NO3	F(000) = 552
Mr = 259.30	Dx = 1.336 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71070 Å
a = 14.0608 (3) Å	Cell parameters from 7564 reflections
b = 6.6407 (1) Å	θ = 1.8–30.0°
c = 14.4581 (3) Å	µ = 0.09 mm^−1
β = 107.312 (1)°	T = 150 K
V = 1288.85 (4) Å^3	Irregular, colourless
Z = 4	0.43 × 0.32 × 0.24 mm

Data collection

Nonius Kappa CCD diffractometer	3285 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
Graphite monochromator	θmax = 30.0°, θmin = 1.8°
ϕ scans and ω scans	h = −19→19
11215 measured reflections	k = −9→9
3749 independent reflections	l = −20→19

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	Hydrogen site location: difference Fourier map
wR(F^2) = 0.123	All H-atom parameters refined
S = 1.15	w = 1/[σ^2(Fo^2) + (0.0361P)^2 + 0.7763P] where P = (Fo^2 + 2Fc^2)/3
3749 reflections	(Δ/σ)max < 0.001
240 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.41374 (8)	0.24094 (17)	0.38486 (8)	0.0209 (2)
O1	0.39383 (7)	−0.07000 (16)	0.48138 (8)	0.0315 (3)
O2	0.12836 (9)	0.39489 (18)	0.39642 (11)	0.0479 (4)
O3	0.64229 (7)	0.25553 (15)	0.19084 (8)	0.0281 (2)
C1	0.30679 (9)	−0.0143 (2)	0.47291 (9)	0.0215 (3)
C2	0.26417 (9)	0.16802 (19)	0.42305 (9)	0.0189 (2)
C3	0.32000 (9)	0.28966 (19)	0.37688 (9)	0.0195 (2)
C4	0.24434 (10)	−0.1449 (2)	0.51788 (11)	0.0288 (3)
C5	0.13503 (10)	−0.1385 (2)	0.45970 (11)	0.0278 (3)
C6	0.09871 (10)	0.0768 (2)	0.45365 (11)	0.0264 (3)
C7	0.16329 (10)	0.2269 (2)	0.42114 (10)	0.0246 (3)
C8	0.27602 (12)	0.4652 (2)	0.31375 (12)	0.0308 (3)
C9	0.48162 (9)	0.34834 (19)	0.34652 (9)	0.0205 (3)
C10	0.52448 (9)	0.2435 (2)	0.28543 (9)	0.0204 (2)
C11	0.59509 (9)	0.3414 (2)	0.25132 (9)	0.0211 (3)
C12	0.62228 (10)	0.5399 (2)	0.27838 (10)	0.0252 (3)
C13	0.57830 (11)	0.6402 (2)	0.33878 (10)	0.0275 (3)
C14	0.50757 (11)	0.5458 (2)	0.37398 (10)	0.0255 (3)
C15	0.61462 (12)	0.0544 (2)	0.15816 (13)	0.0317 (3)
H1	0.4363 (14)	0.128 (3)	0.4203 (14)	0.041 (5)*
H41	0.2505 (14)	−0.088 (3)	0.5855 (14)	0.042 (5)*
H42	0.2714 (15)	−0.279 (3)	0.5244 (14)	0.043 (5)*
H51	0.0945 (14)	−0.225 (3)	0.4910 (14)	0.036 (5)*
H52	0.1290 (14)	−0.197 (3)	0.3911 (14)	0.041 (5)*
H61	0.0934 (14)	0.122 (3)	0.5176 (14)	0.039 (5)*
H62	0.0320 (15)	0.092 (3)	0.4099 (14)	0.039 (5)*
H81	0.3130 (14)	0.493 (3)	0.2698 (13)	0.036 (5)*
H82	0.2080 (16)	0.435 (3)	0.2768 (15)	0.045 (5)*
H83	0.2766 (15)	0.583 (3)	0.3537 (15)	0.043 (5)*
H10	0.5040 (12)	0.106 (3)	0.2668 (12)	0.025 (4)*
H12	0.6744 (13)	0.607 (3)	0.2541 (13)	0.032 (4)*
H13	0.5956 (13)	0.781 (3)	0.3580 (13)	0.033 (5)*
H14	0.4769 (14)	0.615 (3)	0.4175 (13)	0.033 (5)*
H151	0.5423 (15)	0.043 (3)	0.1256 (14)	0.040 (5)*
H152	0.6505 (14)	0.026 (3)	0.1102 (14)	0.038 (5)*
H153	0.6365 (14)	−0.038 (3)	0.2128 (14)	0.039 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0202 (5)	0.0197 (5)	0.0238 (5)	0.0016 (4)	0.0083 (4)	0.0048 (4)
O1	0.0199 (5)	0.0302 (5)	0.0448 (6)	0.0052 (4)	0.0102 (4)	0.0162 (5)
O2	0.0343 (6)	0.0260 (6)	0.0922 (10)	0.0117 (5)	0.0320 (7)	0.0127 (6)
O3	0.0291 (5)	0.0247 (5)	0.0362 (5)	−0.0028 (4)	0.0187 (4)	−0.0009 (4)
C1	0.0183 (5)	0.0234 (6)	0.0215 (6)	−0.0006 (5)	0.0038 (4)	0.0028 (5)
C2	0.0182 (5)	0.0193 (6)	0.0189 (5)	0.0006 (4)	0.0053 (4)	−0.0008 (4)
C3	0.0204 (6)	0.0184 (6)	0.0187 (5)	0.0011 (5)	0.0044 (4)	−0.0008 (4)
C4	0.0210 (6)	0.0317 (8)	0.0330 (7)	−0.0007 (6)	0.0070 (5)	0.0122 (6)
C5	0.0212 (6)	0.0262 (7)	0.0356 (7)	−0.0030 (5)	0.0079 (5)	0.0023 (6)
C6	0.0197 (6)	0.0274 (7)	0.0338 (7)	−0.0006 (5)	0.0106 (5)	−0.0026 (6)
C7	0.0208 (6)	0.0221 (6)	0.0320 (7)	0.0014 (5)	0.0095 (5)	−0.0026 (5)
C8	0.0271 (7)	0.0288 (7)	0.0361 (8)	0.0068 (6)	0.0087 (6)	0.0133 (6)
C9	0.0200 (6)	0.0207 (6)	0.0202 (5)	0.0000 (5)	0.0053 (4)	0.0046 (5)
C10	0.0190 (6)	0.0187 (6)	0.0225 (6)	−0.0007 (5)	0.0047 (4)	0.0032 (5)
C11	0.0195 (6)	0.0224 (6)	0.0214 (6)	0.0002 (5)	0.0059 (4)	0.0039 (5)
C12	0.0251 (6)	0.0231 (6)	0.0269 (6)	−0.0045 (5)	0.0068 (5)	0.0044 (5)
C13	0.0335 (7)	0.0210 (6)	0.0266 (6)	−0.0066 (6)	0.0067 (5)	−0.0002 (5)
C14	0.0310 (7)	0.0233 (6)	0.0227 (6)	−0.0013 (5)	0.0089 (5)	−0.0004 (5)
C15	0.0317 (8)	0.0255 (7)	0.0423 (8)	−0.0007 (6)	0.0176 (7)	−0.0031 (6)

Geometric parameters (Å, º)

N1—C3	1.3283 (16)	C6—H61	0.995 (19)
N1—C9	1.4289 (16)	C6—H62	0.967 (19)
N1—H1	0.91 (2)	C8—H81	0.951 (19)
O1—C1	1.2491 (16)	C8—H82	0.97 (2)
O2—C7	1.2282 (17)	C8—H83	0.97 (2)
O3—C11	1.3695 (16)	C9—C14	1.3869 (19)
O3—C15	1.4315 (18)	C9—C10	1.3946 (18)
C1—C2	1.4450 (18)	C10—C11	1.3937 (17)
C1—C4	1.5117 (18)	C10—H10	0.974 (17)
C2—C3	1.4236 (17)	C11—C12	1.3959 (19)
C2—C7	1.4637 (17)	C12—C13	1.382 (2)
C3—C8	1.4961 (18)	C12—H12	1.007 (18)
C4—C5	1.5173 (19)	C13—C14	1.394 (2)
C4—H41	1.03 (2)	C13—H13	0.987 (19)
C4—H42	0.96 (2)	C14—H14	0.977 (18)
C5—C6	1.512 (2)	C15—H151	0.99 (2)
C5—H51	1.006 (19)	C15—H152	0.989 (19)
C5—H52	1.05 (2)	C15—H153	0.98 (2)
C6—C7	1.5144 (19)
C3—N1—C9	127.21 (11)	O2—C7—C6	117.60 (12)
C3—N1—H1	114.8 (12)	C2—C7—C6	119.04 (12)
C9—N1—H1	117.9 (12)	C3—C8—H81	110.5 (11)
C11—O3—C15	117.60 (11)	C3—C8—H82	109.5 (12)
O1—C1—C2	123.08 (12)	H81—C8—H82	108.5 (16)
O1—C1—C4	117.75 (12)	C3—C8—H83	109.5 (12)
C2—C1—C4	119.17 (11)	H81—C8—H83	109.5 (16)
C3—C2—C1	120.31 (11)	H82—C8—H83	109.3 (17)
C3—C2—C7	120.40 (11)	C14—C9—C10	121.78 (12)
C1—C2—C7	119.29 (11)	C14—C9—N1	120.66 (12)
N1—C3—C2	119.50 (11)	C10—C9—N1	117.46 (11)
N1—C3—C8	117.53 (12)	C11—C10—C9	118.62 (12)
C2—C3—C8	122.86 (12)	C11—C10—H10	121.6 (10)
C1—C4—C5	111.58 (11)	C9—C10—H10	119.8 (10)
C1—C4—H41	107.6 (11)	O3—C11—C10	124.30 (12)
C5—C4—H41	107.5 (11)	O3—C11—C12	115.32 (11)
C1—C4—H42	108.1 (12)	C10—C11—C12	120.38 (12)
C5—C4—H42	112.6 (12)	C13—C12—C11	119.70 (12)
H41—C4—H42	109.2 (16)	C13—C12—H12	121.1 (10)
C6—C5—C4	109.11 (12)	C11—C12—H12	119.2 (10)
C6—C5—H51	109.8 (10)	C12—C13—C14	121.07 (13)
C4—C5—H51	110.5 (11)	C12—C13—H13	121.1 (10)
C6—C5—H52	111.5 (11)	C14—C13—H13	117.8 (10)
C4—C5—H52	107.4 (10)	C9—C14—C13	118.44 (13)
H51—C5—H52	108.5 (15)	C9—C14—H14	120.1 (11)
C5—C6—C7	114.65 (11)	C13—C14—H14	121.5 (11)
C5—C6—H61	110.4 (11)	O3—C15—H151	111.6 (12)
C7—C6—H61	107.9 (11)	O3—C15—H152	105.1 (11)
C5—C6—H62	112.3 (12)	H151—C15—H152	108.6 (15)
C7—C6—H62	106.5 (11)	O3—C15—H153	109.4 (12)
H61—C6—H62	104.5 (15)	H151—C15—H153	111.7 (16)
O2—C7—C2	123.34 (13)	H152—C15—H153	110.2 (16)