(3S,4S)-1-Benzhydryl-4-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-[(S)-1-hydroxy­ethyl]azetidin-2-one

Zhang, H.; Chen, F.-E.; Chen, M.-Q.

doi:10.1107/S160053680702692X

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(3S,4S)-1-Benzhydryl-4-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-[(S)-1-hydroxyethyl]azetidin-2-one

H. Zhang, F.-E. Chen and M.-Q. Chen

Slow diffusion of hexane into an ethyl acetate solution of the title compound, C₂₃H₂₇NO₄, gave X-ray quality crystals. In the crystal structure, intermolecular O—H

O hydrogen bonds link molecules into one-dimensional chains. In addition, weak C—H

O hydrogen bonds help stabilize the crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680702692X/lh2404sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680702692X/lh2404Isup2.hkl Contains datablock I

CCDC reference: 654872

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.048
wR factor = 0.123
Data-to-parameter ratio = 9.5

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT242_ALERT_2_A Check Low       Ueq as Compared to Neighbors for         C9

Author Response: This may be result of marginal disorder but it has not been modelled.


Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.84 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.78 Ratio
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         O3

Alert level C
PLAT048_ALERT_1_C MoietyFormula Not Given ........................          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT153_ALERT_1_C The su's on the Cell Axes   are Equal (x 100000)        400 Ang.
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O4
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C17
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT731_ALERT_1_C Bond    Calc     0.81(4), Rep   0.806(19) ......       2.11 su-Ra
              O2   -H2X     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.81(4), Rep   0.806(19) ......       2.11 su-Ra
              O2   -H2X     1.555   1.555

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.12
           From the CIF: _reflns_number_total               2466
           Count of symmetry unique reflns         2504
           Completeness (_total/calc)             98.48%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7     = .          R
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          2

   1 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   8 ALERT level G = General alerts; check

  11 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

During our study on the synthesis of carbapenems, a class of antibiotics with pronounced broad-spectrum antibacterial activity, (Kawabata et al., 1988), the title compound was produced and is a key intermediate in our newly designed synthetic route to carbapenems. The title compound was synthesized through the reduction of (3S,4S)-3-acetyl-1-benzhydryl-4-((R)-2,2-dimethyl- 1,3-dioxolan-4-yl)-2-azetidinone from L-ascorbic acid. The absolute configuration was difficult to determined by other analytical methods due to the free rotation of C3—C5 single bond. Here we report the crystal structure of the title compound.

Fig. 1 shows the molecular structrue of the title compound. The enantiomer was selected on the basis of the configuration of the starting material. All chiral carbon atoms are S-configuration except C7. The 4-membered ring is almost a planar with a dihedral of 1.2 (2)° for N1—C2—C3—C4, In the 5-membered ring, the dihedral of C9—O4—C7—C8 is 3.4 (4)°, and the dihedral angle of C9/O3/C8/C7 is -18.6 (5)°. The C9—C10 and C9—C11 bond lengths are shorter than the typical Csp³—Csp³ bond distance, possibly as a result of marginal disorder in this area.

Related literature top

For background information, see: Kawabata et al. (1988). For the synthetic procedure, see: Sarko et al. (1996).

Experimental top

The literature procedure according to Sarko et al. (1996) was followed. To a cold (195k) solution of (3S,4S)-3-acetyl-1-benzhydryl -4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-azetidinone (1.0 mmol) in 10 mL of CH₂Cl₂, was added TiCl₄ (110µl, 1.0 mmol) with vigrous stirring under Argon atomsphere. After 10 min, pyr·BH ₃ (140µl, 1.0 mmol) was slowly added. The reaction was quenched with 1 N HCl (2 ml) after 15 min, and the reaction mixture was warmed to r.t., the organic layer was separated and washed with brine, dried over anhyd. MgSO₄, and concentrated in vacuo, Chromatography gave the title compound 28 mg (73%), m.p. 415 K. Full spectroscopic and physical characterization will be reported elsewhere.

Structure description top

For background information, see: Kawabata et al. (1988). For the synthetic procedure, see: Sarko et al. (1996).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The molecular structure drawing for (I) showing 30% probability of displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The packing of the title compound, viewed along the b axis. Hydrogen bonds shown as dashed lines.

(3S,4S)-1-Benzhydryl-4-[(R)-2,2-dimethyl-1,3- dioxolan-4-yl]-3-[(S)-1-hydroxyethyl]-2-azetidinone top

Crystal data top

C₂₃H₂₇NO₄	F(000) = 408
M_r = 381.46	D_x = 1.188 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 769 reflections
a = 10.720 (4) Å	θ = 2.7–23.4°
b = 9.192 (4) Å	µ = 0.08 mm⁻¹
c = 10.819 (4) Å	T = 293 K
β = 90.890 (5)°	Block, colorless
V = 1065.9 (7) Å³	0.15 × 0.15 × 0.12 mm
Z = 2

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2466 independent reflections
Radiation source: fine-focus sealed tube	1973 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
φ and ω scans	θ_max = 27.1°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→13
T_min = 0.988, T_max = 0.990	k = −8→11
5246 measured reflections	l = −13→13

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0578P)² + 0.1569P] where P = (F_o² + 2F_c²)/3
2466 reflections	(Δ/σ)_max < 0.001
260 parameters	Δρ_max = 0.19 e Å⁻³
2 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₂₃H₂₇NO₄	V = 1065.9 (7) Å³
M_r = 381.46	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 10.720 (4) Å	µ = 0.08 mm⁻¹
b = 9.192 (4) Å	T = 293 K
c = 10.819 (4) Å	0.15 × 0.15 × 0.12 mm
β = 90.890 (5)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2466 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1973 reflections with I > 2σ(I)
T_min = 0.988, T_max = 0.990	R_int = 0.026
5246 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	2 restraints
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.19 e Å⁻³
2466 reflections	Δρ_min = −0.13 e Å⁻³
260 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	U_iso*/U_eq
O1	0.2959 (2)	0.5939 (3)	0.5357 (2)	0.0796 (8)
O2	0.5052 (3)	0.1621 (3)	0.6167 (2)	0.0893 (9)
H2X	0.566 (3)	0.135 (6)	0.580 (4)	0.111 (17)*
O3	0.4631 (3)	0.2094 (4)	1.0163 (3)	0.1206 (14)
O4	0.3240 (2)	0.3847 (4)	0.98493 (18)	0.0871 (9)
N1	0.25812 (18)	0.4805 (3)	0.72615 (19)	0.0455 (5)
C2	0.3178 (2)	0.5096 (3)	0.6201 (3)	0.0535 (7)
C3	0.4185 (2)	0.3955 (3)	0.6467 (2)	0.0508 (7)
H3	0.4985	0.4420	0.6668	0.061*
C4	0.3440 (2)	0.3646 (3)	0.7658 (2)	0.0425 (5)
H4	0.3043	0.2685	0.7643	0.051*
C5	0.4357 (3)	0.2721 (4)	0.5551 (3)	0.0673 (9)
H5	0.4845	0.3082	0.4857	0.081*
C6	0.3138 (4)	0.2112 (6)	0.5050 (4)	0.0938 (14)
H6A	0.3305	0.1295	0.4525	0.141*
H6B	0.2707	0.2849	0.4583	0.141*
H6C	0.2629	0.1805	0.5725	0.141*
C7	0.4106 (3)	0.3944 (4)	0.8868 (2)	0.0559 (7)
H7	0.4479	0.4917	0.8853	0.067*
C8	0.5090 (3)	0.2823 (5)	0.9209 (3)	0.0751 (11)
H8A	0.5238	0.2174	0.8520	0.090*
H8B	0.5869	0.3295	0.9440	0.090*
C9	0.3664 (3)	0.2851 (4)	1.0748 (3)	0.0676 (8)
C10	0.2653 (6)	0.1807 (9)	1.1042 (6)	0.163 (3)
H10A	0.1959	0.2325	1.1380	0.244*
H10B	0.2957	0.1110	1.1635	0.244*
H10C	0.2389	0.1312	1.0302	0.244*
C11	0.4124 (6)	0.3664 (8)	1.1846 (4)	0.127 (2)
H11A	0.4768	0.4328	1.1604	0.190*
H11B	0.4455	0.2993	1.2447	0.190*
H11C	0.3448	0.4200	1.2199	0.190*
C12	0.1470 (2)	0.5359 (3)	0.7899 (2)	0.0450 (6)
H12	0.1652	0.5270	0.8786	0.054*
C13	0.1287 (3)	0.6983 (3)	0.7648 (3)	0.0496 (6)
C14	0.0195 (3)	0.7568 (4)	0.7190 (3)	0.0618 (8)
H14	−0.0455	0.6958	0.6947	0.074*
C15	0.0056 (3)	0.9070 (4)	0.7088 (4)	0.0747 (10)
H15	−0.0689	0.9453	0.6779	0.090*
C16	0.0989 (4)	0.9976 (4)	0.7433 (4)	0.0877 (12)
H16	0.0888	1.0979	0.7371	0.105*
C17	0.2092 (4)	0.9395 (4)	0.7879 (5)	0.1029 (16)
H17	0.2743	1.0009	0.8113	0.123*
C18	0.2237 (3)	0.7912 (4)	0.7980 (4)	0.0837 (12)
H18	0.2988	0.7535	0.8277	0.100*
C19	0.0345 (2)	0.4398 (3)	0.7639 (2)	0.0453 (6)
C20	−0.0062 (3)	0.4086 (4)	0.6451 (3)	0.0656 (8)
H20	0.0368	0.4464	0.5784	0.079*
C21	−0.1091 (3)	0.3227 (5)	0.6239 (4)	0.0798 (11)
H21	−0.1352	0.3028	0.5433	0.096*
C22	−0.1727 (3)	0.2669 (5)	0.7205 (4)	0.0815 (11)
H22	−0.2433	0.2106	0.7053	0.098*
C23	−0.1347 (3)	0.2920 (5)	0.8398 (4)	0.0797 (10)
H23	−0.1772	0.2504	0.9053	0.096*
C24	−0.0301 (3)	0.3819 (4)	0.8620 (3)	0.0610 (7)
H24	−0.0045	0.4023	0.9427	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0720 (14)	0.0947 (19)	0.0724 (15)	0.0133 (14)	0.0149 (11)	0.0440 (15)
O2	0.0973 (19)	0.100 (2)	0.0714 (15)	0.0469 (17)	0.0206 (14)	0.0062 (15)
O3	0.136 (3)	0.104 (2)	0.124 (2)	0.064 (2)	0.066 (2)	0.058 (2)
O4	0.0758 (14)	0.140 (3)	0.0460 (11)	0.0508 (17)	0.0084 (10)	0.0085 (14)
N1	0.0405 (10)	0.0474 (13)	0.0487 (11)	0.0027 (10)	0.0049 (8)	0.0084 (10)
C2	0.0450 (13)	0.0583 (18)	0.0573 (16)	0.0002 (13)	0.0058 (11)	0.0156 (15)
C3	0.0385 (12)	0.0630 (18)	0.0512 (14)	0.0037 (12)	0.0094 (10)	0.0127 (14)
C4	0.0426 (12)	0.0394 (13)	0.0457 (13)	0.0022 (11)	0.0069 (10)	0.0031 (11)
C5	0.0659 (17)	0.089 (2)	0.0475 (15)	0.0158 (19)	0.0178 (13)	0.0044 (17)
C6	0.093 (3)	0.118 (4)	0.070 (2)	0.008 (3)	0.001 (2)	−0.030 (2)
C7	0.0565 (15)	0.0640 (19)	0.0471 (14)	0.0067 (14)	0.0006 (11)	−0.0025 (14)
C8	0.0577 (17)	0.112 (3)	0.0558 (17)	0.029 (2)	−0.0008 (14)	0.009 (2)
C9	0.0714 (18)	0.070 (2)	0.0620 (18)	0.0051 (18)	0.0129 (15)	0.0057 (17)
C10	0.177 (6)	0.143 (6)	0.172 (6)	−0.071 (5)	0.089 (5)	−0.030 (5)
C11	0.157 (4)	0.152 (5)	0.070 (2)	0.012 (5)	−0.035 (3)	−0.009 (3)
C12	0.0435 (13)	0.0476 (15)	0.0440 (13)	0.0034 (11)	0.0046 (10)	0.0008 (11)
C13	0.0460 (14)	0.0447 (15)	0.0583 (16)	0.0007 (12)	0.0049 (12)	−0.0006 (13)
C14	0.0498 (16)	0.0489 (17)	0.087 (2)	0.0037 (13)	0.0058 (15)	−0.0006 (16)
C15	0.0621 (18)	0.054 (2)	0.108 (3)	0.0180 (16)	0.0096 (18)	0.0102 (19)
C16	0.085 (3)	0.0405 (17)	0.138 (4)	0.0032 (18)	0.012 (2)	0.003 (2)
C17	0.085 (3)	0.051 (2)	0.172 (5)	−0.012 (2)	−0.022 (3)	−0.009 (3)
C18	0.069 (2)	0.050 (2)	0.131 (3)	−0.0026 (17)	−0.026 (2)	0.001 (2)
C19	0.0368 (12)	0.0401 (14)	0.0592 (15)	0.0045 (10)	0.0031 (11)	−0.0009 (12)
C20	0.0621 (17)	0.068 (2)	0.0663 (18)	−0.0026 (16)	0.0014 (14)	−0.0035 (17)
C21	0.067 (2)	0.079 (3)	0.093 (2)	−0.0069 (19)	−0.0119 (18)	−0.021 (2)
C22	0.0520 (17)	0.068 (2)	0.124 (3)	−0.0136 (18)	0.0027 (19)	−0.013 (2)
C23	0.0549 (17)	0.077 (2)	0.108 (3)	−0.0097 (18)	0.0213 (18)	0.005 (2)
C24	0.0544 (15)	0.0589 (18)	0.0700 (17)	0.0027 (15)	0.0117 (13)	0.0000 (16)

Geometric parameters (Å, º) top

O1—C2	1.218 (4)	C10—H10C	0.9599
O2—C5	1.416 (4)	C11—H11A	0.9599
O2—H2X	0.806 (19)	C11—H11B	0.9599
O3—C8	1.331 (4)	C11—H11C	0.9599
O3—C9	1.408 (4)	C12—C19	1.518 (4)
O4—C9	1.405 (4)	C12—C13	1.529 (4)
O4—C7	1.424 (4)	C12—H12	0.9800
N1—C2	1.349 (3)	C13—C18	1.373 (5)
N1—C4	1.468 (3)	C13—C14	1.374 (4)
N1—C12	1.476 (3)	C14—C15	1.393 (5)
C2—C3	1.529 (4)	C14—H14	0.9300
C3—C5	1.519 (5)	C15—C16	1.349 (5)
C3—C4	1.553 (3)	C15—H15	0.9300
C3—H3	0.9800	C16—C17	1.378 (6)
C4—C7	1.506 (4)	C16—H16	0.9300
C4—H4	0.9800	C17—C18	1.376 (6)
C5—C6	1.515 (5)	C17—H17	0.9300
C5—H5	0.9800	C18—H18	0.9300
C6—H6A	0.9599	C19—C20	1.381 (4)
C6—H6B	0.9599	C19—C24	1.383 (4)
C6—H6C	0.9599	C20—C21	1.373 (5)
C7—C8	1.517 (4)	C20—H20	0.9300
C7—H7	0.9800	C21—C22	1.357 (6)
C8—H8A	0.9700	C21—H21	0.9300
C8—H8B	0.9700	C22—C23	1.367 (5)
C9—C11	1.482 (6)	C22—H22	0.9300
C9—C10	1.486 (6)	C23—C24	1.411 (5)
C10—H10A	0.9599	C23—H23	0.9300
C10—H10B	0.9599	C24—H24	0.9300

C5—O2—H2X	114 (4)	H10A—C10—H10B	109.5
C8—O3—C9	112.5 (3)	C9—C10—H10C	109.5
C9—O4—C7	110.5 (2)	H10A—C10—H10C	109.5
C2—N1—C4	95.11 (19)	H10B—C10—H10C	109.5
C2—N1—C12	136.5 (2)	C9—C11—H11A	109.5
C4—N1—C12	128.4 (2)	C9—C11—H11B	109.5
O1—C2—N1	132.5 (3)	H11A—C11—H11B	109.5
O1—C2—C3	134.8 (3)	C9—C11—H11C	109.5
N1—C2—C3	92.7 (2)	H11A—C11—H11C	109.5
C5—C3—C2	118.8 (2)	H11B—C11—H11C	109.5
C5—C3—C4	118.3 (3)	N1—C12—C19	110.9 (2)
C2—C3—C4	84.89 (18)	N1—C12—C13	110.9 (2)
C5—C3—H3	110.8	C19—C12—C13	115.8 (2)
C2—C3—H3	110.8	N1—C12—H12	106.2
C4—C3—H3	110.8	C19—C12—H12	106.2
N1—C4—C7	114.1 (2)	C13—C12—H12	106.2
N1—C4—C3	87.29 (18)	C18—C13—C14	118.3 (3)
C7—C4—C3	116.4 (2)	C18—C13—C12	117.9 (3)
N1—C4—H4	112.3	C14—C13—C12	123.6 (3)
C7—C4—H4	112.3	C13—C14—C15	120.4 (3)
C3—C4—H4	112.3	C13—C14—H14	119.8
O2—C5—C6	110.5 (4)	C15—C14—H14	119.8
O2—C5—C3	107.1 (2)	C16—C15—C14	120.8 (3)
C6—C5—C3	113.4 (3)	C16—C15—H15	119.6
O2—C5—H5	108.6	C14—C15—H15	119.6
C6—C5—H5	108.6	C15—C16—C17	119.1 (3)
C3—C5—H5	108.6	C15—C16—H16	120.5
C5—C6—H6A	109.5	C17—C16—H16	120.5
C5—C6—H6B	109.5	C18—C17—C16	120.5 (4)
H6A—C6—H6B	109.5	C18—C17—H17	119.8
C5—C6—H6C	109.5	C16—C17—H17	119.8
H6A—C6—H6C	109.5	C13—C18—C17	120.9 (4)
H6B—C6—H6C	109.5	C13—C18—H18	119.6
O4—C7—C4	109.3 (2)	C17—C18—H18	119.6
O4—C7—C8	103.6 (2)	C20—C19—C24	118.7 (3)
C4—C7—C8	114.0 (3)	C20—C19—C12	122.1 (3)
O4—C7—H7	109.9	C24—C19—C12	119.2 (2)
C4—C7—H7	109.9	C21—C20—C19	121.1 (3)
C8—C7—H7	109.9	C21—C20—H20	119.5
O3—C8—C7	105.5 (2)	C19—C20—H20	119.5
O3—C8—H8A	110.6	C22—C21—C20	120.1 (3)
C7—C8—H8A	110.6	C22—C21—H21	120.0
O3—C8—H8B	110.6	C20—C21—H21	120.0
C7—C8—H8B	110.6	C21—C22—C23	121.1 (3)
H8A—C8—H8B	108.8	C21—C22—H22	119.4
O4—C9—O3	104.1 (2)	C23—C22—H22	119.4
O4—C9—C11	109.0 (4)	C22—C23—C24	118.9 (3)
O3—C9—C11	111.8 (4)	C22—C23—H23	120.5
O4—C9—C10	109.9 (4)	C24—C23—H23	120.5
O3—C9—C10	108.8 (4)	C19—C24—C23	120.0 (3)
C11—C9—C10	112.9 (4)	C19—C24—H24	120.0
C9—C10—H10A	109.5	C23—C24—H24	120.0
C9—C10—H10B	109.5

C4—N1—C2—O1	177.6 (4)	C8—O3—C9—O4	20.7 (5)
C12—N1—C2—O1	−2.4 (6)	C8—O3—C9—C11	−96.9 (5)
C4—N1—C2—C3	−1.3 (2)	C8—O3—C9—C10	137.8 (5)
C12—N1—C2—C3	178.8 (3)	C2—N1—C12—C19	97.6 (4)
O1—C2—C3—C5	−58.0 (5)	C4—N1—C12—C19	−82.4 (3)
N1—C2—C3—C5	120.8 (3)	C2—N1—C12—C13	−32.6 (4)
O1—C2—C3—C4	−177.6 (4)	C4—N1—C12—C13	147.4 (3)
N1—C2—C3—C4	1.2 (2)	N1—C12—C13—C18	−58.6 (4)
C2—N1—C4—C7	119.1 (2)	C19—C12—C13—C18	173.9 (3)
C12—N1—C4—C7	−61.0 (3)	N1—C12—C13—C14	126.2 (3)
C2—N1—C4—C3	1.2 (2)	C19—C12—C13—C14	−1.4 (4)
C12—N1—C4—C3	−178.8 (3)	C18—C13—C14—C15	−1.0 (5)
C5—C3—C4—N1	−121.2 (2)	C12—C13—C14—C15	174.2 (3)
C2—C3—C4—N1	−1.1 (2)	C13—C14—C15—C16	0.2 (6)
C5—C3—C4—C7	123.1 (3)	C14—C15—C16—C17	0.6 (7)
C2—C3—C4—C7	−116.8 (3)	C15—C16—C17—C18	−0.5 (8)
C2—C3—C5—O2	−163.1 (3)	C14—C13—C18—C17	1.2 (7)
C4—C3—C5—O2	−62.6 (3)	C12—C13—C18—C17	−174.3 (5)
C2—C3—C5—C6	−40.9 (4)	C16—C17—C18—C13	−0.4 (9)
C4—C3—C5—C6	59.5 (4)	N1—C12—C19—C20	−55.3 (3)
C9—O4—C7—C4	125.3 (3)	C13—C12—C19—C20	72.3 (3)
C9—O4—C7—C8	3.4 (4)	N1—C12—C19—C24	125.1 (3)
N1—C4—C7—O4	70.7 (3)	C13—C12—C19—C24	−107.4 (3)
C3—C4—C7—O4	170.2 (3)	C24—C19—C20—C21	0.4 (5)
N1—C4—C7—C8	−173.9 (2)	C12—C19—C20—C21	−179.2 (3)
C3—C4—C7—C8	−74.5 (3)	C19—C20—C21—C22	0.0 (6)
C9—O3—C8—C7	−18.6 (5)	C20—C21—C22—C23	−1.4 (6)
O4—C7—C8—O3	9.0 (4)	C21—C22—C23—C24	2.3 (6)
C4—C7—C8—O3	−109.7 (4)	C20—C19—C24—C23	0.5 (5)
C7—O4—C9—O3	−13.8 (4)	C12—C19—C24—C23	−179.8 (3)
C7—O4—C9—C11	105.7 (4)	C22—C23—C24—C19	−1.8 (5)
C7—O4—C9—C10	−130.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O4	0.98	2.42	3.141 (3)	130
O2—H2X···O1ⁱ	0.81 (2)	1.99 (2)	2.787 (4)	170 (5)
C7—H7···O3ⁱⁱ	0.98	2.45	3.357 (4)	153

Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) −x+1, y+1/2, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₇NO₄
M_r	381.46
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	10.720 (4), 9.192 (4), 10.819 (4)
β (°)	90.890 (5)
V (Å³)	1065.9 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.15 × 0.15 × 0.12

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.988, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	5246, 2466, 1973
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.123, 1.02
No. of reflections	2466
No. of parameters	260
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.13

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000), SHELXTL.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O4	0.98	2.42	3.141 (3)	129.6
O2—H2X···O1ⁱ	0.806 (19)	1.99 (2)	2.787 (4)	170 (5)
C7—H7···O3ⁱⁱ	0.98	2.45	3.357 (4)	153.3

Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) −x+1, y+1/2, −z+2.

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