(R*)-(−)-3-[4-(Benz­yloxy)benzoyl­meth­yl] 5-ethyl 2,6-dimethyl-4-(3-nitro­phen­yl)-1,4-dihydro­pyridine-3,5-dicarboxyl­ate

Wu, X.-Y.; Hu, A.-X.; Cao, G.

doi:10.1107/S1600536807054785

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(R*)-(−)-3-[4-(Benzyloxy)benzoylmethyl] 5-ethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

X.-Y. Wu, A.-X. Hu and G. Cao

In the optically active title compound, C₃₂H₃₀N₂O₈, the substituted 1,4-dihydropyridine ring adopts a flattened boat conformation. The crystal structure is stabilized by intermolecular N—H

O hydrogen bonding.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807054785/xu2347sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807054785/xu2347Isup2.hkl Contains datablock I

CCDC reference: 672847

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.009 Å
R factor = 0.045
wR factor = 0.144
Data-to-parameter ratio = 7.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.35
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        200 Deg.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.77 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       3.12 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C12    -   C13     ..       5.04 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C23
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C30
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C9
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C21
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          9

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           26.00
           From the CIF: _reflns_number_total               2808
           Count of symmetry unique reflns         2856
           Completeness (_total/calc)             98.32%
           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
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3     = .          S
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          3

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 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

1,4-dihydropyridine derivatives have been widely investigated from the pharmacological point of view since Nifedipine was found to be highly effective calcium antagonist in 1975, and many compounds similar to Nifedipine in structure have already been widely used as therapeutic agents for the treatment of cerebra circulatory disorder, hypertension and so on (Goldmann & Stoltefuss 1991). According to the structure–activity relationship of 1,4-dihydropyridine calcium antagonists, a serials of new compounds were designed and synthesized (Wu et al., 2006). The optical active title compound has been synthesized by the reaction of optical active 1,4-dihydropyridine monoester with a\-bromoalkylaryl ketone under mild conditions.

The 1,4-dihydropyridne (DHP) ring has a flattened boat conformation, N1 and C3 deviating from the mean plane by -0.185 (4) Å and -0.247 (5) Å, respectively. The dihedral angle found between plane C1/C2/C4/C5 and C2/C3/C4, C1/N1/N5 are 31.1° and 18.4°, respectively. Both the 3-nitrophenyl ring (C27–C32) and the DHP ring (N1, C1, C2, C3, C4, C5) are almost perpendicular to each other, the dihedral angle found between them is 80.8 (3)°. The phenyl rings C14/C15/C16/C17/C18/C19 and C21/C22/C23/C24/C25/C26 are almost perpendicular to each other, too, the dihedral angle found between them is 87.5 (3)°. The structure has intermolecular hydrogen bonds of the type N—H···O between the amine of one molecule and the carbonyl oxygen of neighbouring molecule.

Related literature top

The importance of 1,4-dihydropyridine derivatives was summarized by Goldmann & Stoltefuss (1991). A series of new 1,4-dihydropyridine compounds has been designed and synthesized by us (Wu et al., 2006).

Experimental top

Cinchonidine (15 mmol) and racemic acid 1,4-dihydropyridine monoester, ethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate (15 mmol) were stirred in reflux ethanol (35 ml) until the dissolution was complete, and then kept at room temperature for 24 h. The crystals formed were collected by filtration to give Cinchonidine salt (3.1 g). The 1,4-dihydropyridine monoester was obtained by dissolving of the Cinchonidine salt and sodium hydroxide in water. The solution were acidified with HCl, filtered, washed with water to give (-)-ethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate (1.54 g, yield 31%, [α]_D²⁰ = -4.4°). The absolute configuration of the enantiomer has not been assigned.

Optical active 1,4-dihydropyridine monoester (5 mmol), 2-bromo-1-(4-benzyloxyphenyl)ethan-1-one (5 mmol) and K₂CO₃ (5 mmol) in DMF (5 ml) were stirred overnight at room temperature. The mixture was extracted with ethyl acetate, washed successively with water and brine, and then dried and the solvent was removed. The residue was purified by crystallization to give target compound (yield 75%, [α]_D²⁰ = -93.1°).

Crystals suitable for X-ray analysis were obtained by slow evaporation from saturated methanol solution.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).

Figures top

	Fig. 1. Molecular structure of (I) showing 30% probability displacement ellipsoids.
	Fig. 2. Packing diagram.

(R*)-(-)-3-[4-(Benzyloxy)benzoylmethyl] 5-ethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate top

Crystal data top

C₃₂H₃₀N₂O₈	Z = 1
M_r = 570.58	F(000) = 300
Triclinic, P1	D_x = 1.301 Mg m⁻³
Hall symbol: P 1	Melting point: 122 K
a = 7.3646 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.1772 (8) Å	Cell parameters from 1853 reflections
c = 13.329 (1) Å	µ = 0.09 mm⁻¹
α = 97.905 (2)°	T = 295 K
β = 100.352 (2)°	Block, yellow
γ = 109.296 (2)°	0.46 × 0.28 × 0.16 mm
V = 728.33 (12) Å³

Data collection top

Bruker SMART 1000 CCD diffractometer	1747 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.030
Graphite monochromator	θ_max = 26.0°, θ_min = 1.6°
ω scans	h = −9→9
5566 measured reflections	k = −10→10
2808 independent reflections	l = −16→16

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.144	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0853P)²] where P = (F_o² + 2F_c²)/3
2808 reflections	(Δ/σ)_max < 0.001
382 parameters	Δρ_max = 0.21 e Å⁻³
3 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₃₂H₃₀N₂O₈	γ = 109.296 (2)°
M_r = 570.58	V = 728.33 (12) Å³
Triclinic, P1	Z = 1
a = 7.3646 (7) Å	Mo Kα radiation
b = 8.1772 (8) Å	µ = 0.09 mm⁻¹
c = 13.329 (1) Å	T = 295 K
α = 97.905 (2)°	0.46 × 0.28 × 0.16 mm
β = 100.352 (2)°

Data collection top

Bruker SMART 1000 CCD diffractometer	1747 reflections with I > 2σ(I)
5566 measured reflections	R_int = 0.030
2808 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	3 restraints
wR(F²) = 0.144	H-atom parameters constrained
S = 1.02	Δρ_max = 0.21 e Å⁻³
2808 reflections	Δρ_min = −0.21 e Å⁻³
382 parameters

Special details top

Experimental. ¹H NMR (CDCl₃, 400 MHz) (p.p.m.): 1.22 (t, J = 7.2 Hz, 3H, CH₃),2.39 (s, 3H, CH₃), 2.42(s, 3H, CH₃), 3.96–4.13 (m, 2H, CH₂), 5.13 (s, 2H, CH₂), 5.20 (s, 1H, DHP 4-H), 5.24, 5.29 (dd, J =16.4 Hz, J =16.4 Hz, 2H, CO₂CH₂CO), 5.98 (s, 1H, NH), 6.97–8.13 (m, 13H, Ar—H).

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
C1	0.6718 (6)	0.3591 (6)	0.7572 (4)	0.0533 (11)
C2	0.5034 (6)	0.3903 (6)	0.7313 (4)	0.0513 (10)
C3	0.3081 (6)	0.2467 (6)	0.7268 (4)	0.0536 (11)
H3	0.2150	0.3049	0.7396	0.064*
C4	0.3348 (6)	0.1501 (5)	0.8135 (3)	0.0480 (10)
C5	0.5090 (6)	0.1267 (6)	0.8418 (4)	0.0556 (11)
C6	0.5611 (8)	0.0160 (8)	0.9149 (5)	0.0800 (16)
H6A	0.5869	0.0777	0.9856	0.120*
H6B	0.6771	−0.0053	0.9034	0.120*
H6C	0.4526	−0.0950	0.9023	0.120*
C7	0.8763 (7)	0.4639 (7)	0.7483 (5)	0.0768 (15)
H7A	0.8718	0.4784	0.6777	0.115*
H7B	0.9635	0.4022	0.7671	0.115*
H7C	0.9243	0.5783	0.7943	0.115*
C8	0.1677 (6)	0.0884 (5)	0.8604 (4)	0.0500 (10)
C9	0.0365 (8)	−0.0586 (8)	0.9877 (5)	0.0772 (15)
H9A	−0.0854	−0.1386	0.9389	0.093*
H9B	0.0125	0.0431	1.0207	0.093*
C10	0.1013 (11)	−0.1492 (11)	1.0668 (6)	0.111 (2)
H10A	0.1136	−0.2552	1.0329	0.167*
H10B	0.0055	−0.1795	1.1079	0.167*
H10C	0.2273	−0.0721	1.1111	0.167*
C11	0.4911 (7)	0.5559 (6)	0.7029 (4)	0.0564 (11)
C12	0.6556 (7)	0.8139 (6)	0.6503 (4)	0.0625 (13)
H12A	0.7818	0.9123	0.6706	0.075*
H12B	0.5550	0.8575	0.6674	0.075*
C13	0.6058 (6)	0.7412 (6)	0.5350 (4)	0.0586 (12)
C14	0.5909 (6)	0.8605 (6)	0.4637 (4)	0.0572 (11)
C15	0.6281 (7)	1.0397 (6)	0.4971 (4)	0.0591 (12)
H15	0.6646	1.0887	0.5683	0.071*
C16	0.6120 (7)	1.1463 (6)	0.4269 (4)	0.0618 (12)
H16	0.6336	1.2650	0.4510	0.074*
C17	0.5640 (7)	1.0775 (7)	0.3213 (4)	0.0659 (13)
C18	0.5269 (10)	0.8964 (8)	0.2864 (5)	0.0866 (17)
H18	0.4928	0.8473	0.2154	0.104*
C19	0.5412 (9)	0.7935 (7)	0.3575 (4)	0.0814 (17)
H19	0.5167	0.6741	0.3336	0.098*
C20	0.5785 (11)	1.3511 (7)	0.2736 (5)	0.0891 (17)
H20A	0.7176	1.4170	0.3065	0.107*
H20B	0.5006	1.3707	0.3222	0.107*
C21	0.5186 (10)	1.4100 (7)	0.1744 (5)	0.0808 (17)
C22	0.6499 (12)	1.4713 (10)	0.1165 (6)	0.111 (2)
H22	0.7793	1.4753	0.1362	0.134*
C23	0.5874 (18)	1.5295 (11)	0.0251 (7)	0.134 (3)
H23	0.6765	1.5753	−0.0144	0.161*
C24	0.3984 (18)	1.5174 (9)	−0.0035 (7)	0.116 (3)
H24	0.3568	1.5530	−0.0640	0.140*
C25	0.2676 (13)	1.4550 (9)	0.0537 (6)	0.106 (2)
H25	0.1375	1.4486	0.0330	0.127*
C26	0.3276 (12)	1.4010 (8)	0.1424 (5)	0.0929 (19)
H26	0.2370	1.3574	0.1816	0.111*
C27	0.2206 (6)	0.1232 (7)	0.6193 (4)	0.0579 (12)
C28	0.1756 (7)	0.1925 (9)	0.5333 (4)	0.0755 (15)
H28	0.1954	0.3125	0.5424	0.091*
C29	0.1031 (8)	0.0886 (13)	0.4355 (5)	0.093 (2)
C30	0.0708 (9)	−0.0890 (15)	0.4179 (6)	0.111 (3)
H30	0.0221	−0.1584	0.3506	0.133*
C31	0.1123 (9)	−0.1625 (10)	0.5025 (6)	0.098 (2)
H31	0.0912	−0.2828	0.4921	0.117*
C32	0.1851 (7)	−0.0585 (7)	0.6024 (5)	0.0731 (14)
H32	0.2106	−0.1098	0.6588	0.088*
N1	0.6607 (5)	0.2105 (5)	0.7986 (3)	0.0565 (10)
H1	0.7535	0.1688	0.7972	0.068*
N2	0.0568 (10)	0.1652 (16)	0.3455 (6)	0.128 (3)
O1	0.0167 (4)	0.1171 (4)	0.8359 (2)	0.0587 (8)
O2	0.1918 (5)	−0.0024 (5)	0.9338 (3)	0.0745 (10)
O3	0.3392 (5)	0.5796 (4)	0.6805 (3)	0.0800 (11)
O4	0.6662 (4)	0.6790 (4)	0.7062 (3)	0.0647 (9)
O5	0.5795 (7)	0.5867 (5)	0.5045 (3)	0.0899 (12)
O6	0.5427 (6)	1.1658 (5)	0.2441 (3)	0.0836 (11)
O7	0.0752 (11)	0.3189 (14)	0.3632 (6)	0.162 (3)
O8	0.0010 (11)	0.0749 (14)	0.2595 (5)	0.183 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.046 (2)	0.050 (3)	0.072 (3)	0.026 (2)	0.020 (2)	0.013 (2)
C2	0.044 (2)	0.052 (3)	0.069 (3)	0.026 (2)	0.018 (2)	0.018 (2)
C3	0.038 (2)	0.064 (3)	0.075 (3)	0.034 (2)	0.020 (2)	0.021 (2)
C4	0.039 (2)	0.047 (2)	0.065 (3)	0.0227 (18)	0.0138 (19)	0.011 (2)
C5	0.048 (2)	0.055 (3)	0.077 (3)	0.030 (2)	0.021 (2)	0.020 (2)
C6	0.063 (3)	0.087 (4)	0.119 (5)	0.049 (3)	0.030 (3)	0.049 (3)
C7	0.052 (3)	0.068 (3)	0.124 (5)	0.030 (2)	0.032 (3)	0.031 (3)
C8	0.043 (2)	0.046 (2)	0.063 (3)	0.0201 (19)	0.009 (2)	0.012 (2)
C9	0.067 (3)	0.088 (4)	0.100 (4)	0.040 (3)	0.033 (3)	0.047 (3)
C10	0.115 (5)	0.124 (6)	0.121 (6)	0.058 (5)	0.035 (4)	0.065 (5)
C11	0.053 (3)	0.057 (3)	0.071 (3)	0.031 (2)	0.021 (2)	0.016 (2)
C12	0.055 (3)	0.040 (2)	0.093 (4)	0.019 (2)	0.015 (2)	0.017 (2)
C13	0.053 (3)	0.045 (3)	0.075 (3)	0.018 (2)	0.017 (2)	0.005 (2)
C14	0.056 (3)	0.041 (2)	0.077 (3)	0.022 (2)	0.018 (2)	0.009 (2)
C15	0.059 (3)	0.046 (3)	0.071 (3)	0.016 (2)	0.019 (2)	0.009 (2)
C16	0.069 (3)	0.042 (2)	0.075 (4)	0.021 (2)	0.019 (3)	0.010 (3)
C17	0.074 (3)	0.061 (3)	0.070 (4)	0.034 (2)	0.016 (3)	0.015 (3)
C18	0.125 (5)	0.067 (3)	0.071 (4)	0.052 (3)	0.011 (3)	−0.001 (3)
C19	0.116 (5)	0.053 (3)	0.076 (4)	0.046 (3)	0.005 (3)	0.000 (3)
C20	0.122 (5)	0.058 (3)	0.087 (4)	0.034 (3)	0.021 (3)	0.014 (3)
C21	0.115 (5)	0.047 (3)	0.070 (4)	0.020 (3)	0.019 (4)	0.009 (3)
C22	0.119 (5)	0.112 (6)	0.093 (5)	0.023 (4)	0.037 (4)	0.022 (4)
C23	0.178 (9)	0.099 (6)	0.083 (6)	−0.012 (6)	0.047 (6)	0.019 (4)
C24	0.174 (9)	0.066 (4)	0.089 (5)	0.023 (5)	0.021 (6)	0.017 (4)
C25	0.142 (6)	0.078 (4)	0.102 (5)	0.056 (4)	0.014 (5)	0.008 (4)
C26	0.133 (6)	0.073 (4)	0.088 (5)	0.051 (4)	0.035 (4)	0.024 (3)
C27	0.032 (2)	0.078 (3)	0.064 (3)	0.020 (2)	0.0151 (19)	0.010 (3)
C28	0.046 (3)	0.109 (4)	0.073 (4)	0.022 (3)	0.020 (3)	0.028 (3)
C29	0.054 (3)	0.142 (7)	0.070 (5)	0.019 (4)	0.019 (3)	0.019 (5)
C30	0.059 (4)	0.161 (9)	0.079 (5)	0.017 (5)	0.012 (3)	−0.018 (5)
C31	0.066 (4)	0.098 (5)	0.105 (6)	0.021 (3)	0.013 (4)	−0.024 (5)
C32	0.054 (3)	0.073 (4)	0.089 (4)	0.026 (3)	0.015 (3)	0.003 (3)
N1	0.044 (2)	0.053 (2)	0.088 (3)	0.0314 (17)	0.0222 (19)	0.021 (2)
N2	0.086 (4)	0.201 (9)	0.078 (5)	0.020 (5)	0.026 (4)	0.042 (6)
O1	0.0424 (17)	0.068 (2)	0.078 (2)	0.0295 (15)	0.0182 (14)	0.0267 (17)
O2	0.060 (2)	0.095 (3)	0.100 (3)	0.0494 (19)	0.0328 (18)	0.055 (2)
O3	0.065 (2)	0.071 (2)	0.134 (3)	0.0450 (19)	0.039 (2)	0.047 (2)
O4	0.0558 (19)	0.0481 (19)	0.090 (2)	0.0204 (15)	0.0090 (16)	0.0197 (17)
O5	0.134 (3)	0.043 (2)	0.095 (3)	0.036 (2)	0.029 (2)	0.0092 (19)
O6	0.122 (3)	0.056 (2)	0.076 (2)	0.041 (2)	0.017 (2)	0.0108 (19)
O7	0.133 (5)	0.211 (8)	0.117 (5)	0.023 (6)	0.004 (4)	0.086 (6)
O8	0.159 (6)	0.289 (10)	0.069 (4)	0.050 (6)	0.022 (3)	0.024 (5)

Geometric parameters (Å, º) top

C1—C2	1.343 (5)	C15—H15	0.9300
C1—N1	1.386 (6)	C16—C17	1.376 (7)
C1—C7	1.502 (7)	C16—H16	0.9300
C2—C11	1.481 (6)	C17—O6	1.350 (6)
C2—C3	1.511 (6)	C17—C18	1.407 (7)
C3—C4	1.507 (6)	C18—C19	1.363 (8)
C3—C27	1.525 (7)	C18—H18	0.9300
C3—H3	0.9800	C19—H19	0.9300
C4—C5	1.354 (5)	C20—O6	1.434 (6)
C4—C8	1.454 (6)	C20—C21	1.510 (9)
C5—N1	1.372 (6)	C20—H20A	0.9700
C5—C6	1.501 (6)	C20—H20B	0.9700
C6—H6A	0.9600	C21—C22	1.355 (9)
C6—H6B	0.9600	C21—C26	1.369 (9)
C6—H6C	0.9600	C22—C23	1.423 (12)
C7—H7A	0.9600	C22—H22	0.9300
C7—H7B	0.9600	C23—C24	1.341 (13)
C7—H7C	0.9600	C23—H23	0.9300
C8—O1	1.209 (4)	C24—C25	1.347 (11)
C8—O2	1.328 (5)	C24—H24	0.9300
C9—O2	1.440 (6)	C25—C26	1.368 (10)
C9—C10	1.468 (8)	C25—H25	0.9300
C9—H9A	0.9700	C26—H26	0.9300
C9—H9B	0.9700	C27—C28	1.383 (7)
C10—H10A	0.9600	C27—C32	1.398 (7)
C10—H10B	0.9600	C28—C29	1.360 (9)
C10—H10C	0.9600	C28—H28	0.9300
C11—O3	1.191 (5)	C29—C30	1.370 (11)
C11—O4	1.337 (5)	C29—N2	1.466 (10)
C12—O4	1.429 (5)	C30—C31	1.382 (11)
C12—C13	1.501 (7)	C30—H30	0.9300
C12—H12A	0.9700	C31—C32	1.384 (9)
C12—H12B	0.9700	C31—H31	0.9300
C13—O5	1.211 (5)	C32—H32	0.9300
C13—C14	1.467 (7)	N1—H1	0.8600
C14—C19	1.381 (7)	N2—O8	1.195 (10)
C14—C15	1.390 (6)	N2—O7	1.203 (11)
C15—C16	1.380 (7)

C2—C1—N1	117.2 (4)	C17—C16—C15	120.3 (4)
C2—C1—C7	129.1 (4)	C17—C16—H16	119.9
N1—C1—C7	113.8 (4)	C15—C16—H16	119.9
C1—C2—C11	124.9 (4)	O6—C17—C16	126.6 (4)
C1—C2—C3	119.1 (4)	O6—C17—C18	114.5 (5)
C11—C2—C3	115.9 (3)	C16—C17—C18	118.9 (5)
C4—C3—C2	109.4 (3)	C19—C18—C17	119.6 (5)
C4—C3—C27	113.0 (4)	C19—C18—H18	120.2
C2—C3—C27	111.7 (4)	C17—C18—H18	120.2
C4—C3—H3	107.5	C18—C19—C14	122.3 (5)
C2—C3—H3	107.5	C18—C19—H19	118.9
C27—C3—H3	107.5	C14—C19—H19	118.9
C5—C4—C8	125.0 (4)	O6—C20—C21	106.6 (5)
C5—C4—C3	118.7 (4)	O6—C20—H20A	110.4
C8—C4—C3	116.4 (3)	C21—C20—H20A	110.4
C4—C5—N1	118.0 (4)	O6—C20—H20B	110.4
C4—C5—C6	128.4 (4)	C21—C20—H20B	110.4
N1—C5—C6	113.6 (4)	H20A—C20—H20B	108.6
C5—C6—H6A	109.5	C22—C21—C26	119.4 (7)
C5—C6—H6B	109.5	C22—C21—C20	121.4 (7)
H6A—C6—H6B	109.5	C26—C21—C20	119.2 (6)
C5—C6—H6C	109.5	C21—C22—C23	119.2 (8)
H6A—C6—H6C	109.5	C21—C22—H22	120.4
H6B—C6—H6C	109.5	C23—C22—H22	120.4
C1—C7—H7A	109.5	C24—C23—C22	119.3 (8)
C1—C7—H7B	109.5	C24—C23—H23	120.4
H7A—C7—H7B	109.5	C22—C23—H23	120.4
C1—C7—H7C	109.5	C23—C24—C25	121.5 (8)
H7A—C7—H7C	109.5	C23—C24—H24	119.3
H7B—C7—H7C	109.5	C25—C24—H24	119.3
O1—C8—O2	121.5 (4)	C24—C25—C26	119.5 (8)
O1—C8—C4	123.3 (4)	C24—C25—H25	120.3
O2—C8—C4	115.3 (3)	C26—C25—H25	120.3
O2—C9—C10	107.6 (5)	C25—C26—C21	121.2 (7)
O2—C9—H9A	110.2	C25—C26—H26	119.4
C10—C9—H9A	110.2	C21—C26—H26	119.4
O2—C9—H9B	110.2	C28—C27—C32	117.5 (5)
C10—C9—H9B	110.2	C28—C27—C3	119.2 (5)
H9A—C9—H9B	108.5	C32—C27—C3	123.3 (4)
C9—C10—H10A	109.5	C29—C28—C27	121.3 (6)
C9—C10—H10B	109.5	C29—C28—H28	119.4
H10A—C10—H10B	109.5	C27—C28—H28	119.4
C9—C10—H10C	109.5	C28—C29—C30	121.6 (7)
H10A—C10—H10C	109.5	C28—C29—N2	120.3 (8)
H10B—C10—H10C	109.5	C30—C29—N2	118.1 (8)
O3—C11—O4	122.4 (4)	C29—C30—C31	118.4 (7)
O3—C11—C2	123.3 (4)	C29—C30—H30	120.8
O4—C11—C2	114.3 (3)	C31—C30—H30	120.8
O4—C12—C13	110.2 (4)	C30—C31—C32	120.5 (7)
O4—C12—H12A	109.6	C30—C31—H31	119.7
C13—C12—H12A	109.6	C32—C31—H31	119.7
O4—C12—H12B	109.6	C31—C32—C27	120.6 (6)
C13—C12—H12B	109.6	C31—C32—H32	119.7
H12A—C12—H12B	108.1	C27—C32—H32	119.7
O5—C13—C14	122.7 (5)	C5—N1—C1	123.2 (3)
O5—C13—C12	118.8 (4)	C5—N1—H1	118.4
C14—C13—C12	118.5 (4)	C1—N1—H1	118.4
C19—C14—C15	117.6 (4)	O8—N2—O7	123.0 (10)
C19—C14—C13	118.8 (4)	O8—N2—C29	119.9 (11)
C15—C14—C13	123.6 (4)	O7—N2—C29	117.0 (9)
C16—C15—C14	121.3 (5)	C8—O2—C9	118.1 (3)
C16—C15—H15	119.3	C11—O4—C12	114.9 (3)
C14—C15—H15	119.3	C17—O6—C20	117.7 (4)

N1—C1—C2—C11	169.2 (5)	O6—C20—C21—C26	90.2 (8)
C7—C1—C2—C11	−10.9 (10)	C26—C21—C22—C23	1.6 (13)
N1—C1—C2—C3	−12.7 (8)	C20—C21—C22—C23	−178.5 (7)
C7—C1—C2—C3	167.3 (6)	C21—C22—C23—C24	−1.8 (15)
C1—C2—C3—C4	37.5 (7)	C22—C23—C24—C25	0.9 (15)
C11—C2—C3—C4	−144.2 (4)	C23—C24—C25—C26	0.1 (14)
C1—C2—C3—C27	−88.2 (6)	C22—C21—C26—C25	−0.6 (11)
C11—C2—C3—C27	90.2 (5)	C20—C21—C26—C25	179.6 (7)
C2—C3—C4—C5	−34.7 (7)	C24—C25—C26—C21	−0.3 (12)
C27—C3—C4—C5	90.4 (6)	C4—C3—C27—C28	175.7 (4)
C2—C3—C4—C8	145.3 (4)	C2—C3—C27—C28	−60.5 (5)
C27—C3—C4—C8	−89.6 (5)	C4—C3—C27—C32	−5.1 (6)
C8—C4—C5—N1	−172.5 (5)	C2—C3—C27—C32	118.6 (5)
C3—C4—C5—N1	7.5 (8)	C32—C27—C28—C29	−1.5 (8)
C8—C4—C5—C6	8.7 (9)	C3—C27—C28—C29	177.7 (5)
C3—C4—C5—C6	−171.3 (6)	C27—C28—C29—C30	0.7 (10)
C5—C4—C8—O1	177.0 (6)	C27—C28—C29—N2	179.9 (6)
C3—C4—C8—O1	−3.0 (7)	C28—C29—C30—C31	0.2 (11)
C5—C4—C8—O2	−2.5 (8)	N2—C29—C30—C31	−179.0 (7)
C3—C4—C8—O2	177.5 (5)	C29—C30—C31—C32	−0.1 (11)
C1—C2—C11—O3	−179.9 (6)	C30—C31—C32—C27	−0.7 (10)
C3—C2—C11—O3	1.9 (8)	C28—C27—C32—C31	1.5 (8)
C1—C2—C11—O4	−0.6 (8)	C3—C27—C32—C31	−177.6 (6)
C3—C2—C11—O4	−178.8 (5)	C4—C5—N1—C1	22.3 (8)
O4—C12—C13—O5	1.0 (7)	C6—C5—N1—C1	−158.7 (6)
O4—C12—C13—C14	−179.2 (4)	C2—C1—N1—C5	−19.6 (8)
O5—C13—C14—C19	1.0 (9)	C7—C1—N1—C5	160.5 (6)
C12—C13—C14—C19	−178.6 (5)	C28—C29—N2—O7	−3.1 (13)
O5—C13—C14—C15	−177.5 (6)	C30—C29—N2—O7	176.1 (10)
C12—C13—C14—C15	2.8 (8)	C28—C29—N2—O8	176.7 (8)
C19—C14—C15—C16	1.4 (8)	C30—C29—N2—O8	−4.1 (12)
C13—C14—C15—C16	180.0 (5)	O1—C8—O2—C9	−3.0 (8)
C14—C15—C16—C17	−2.1 (8)	C4—C8—O2—C9	176.5 (5)
C15—C16—C17—O6	179.8 (6)	C10—C9—O2—C8	−177.6 (7)
C15—C16—C17—C18	1.5 (9)	O3—C11—O4—C12	−19.1 (8)
O6—C17—C18—C19	−178.8 (7)	C2—C11—O4—C12	161.6 (5)
C16—C17—C18—C19	−0.3 (11)	C13—C12—O4—C11	−73.8 (6)
C17—C18—C19—C14	−0.4 (12)	C16—C17—O6—C20	1.9 (10)
C15—C14—C19—C18	−0.2 (10)	C18—C17—O6—C20	−179.8 (7)
C13—C14—C19—C18	−178.8 (7)	C21—C20—O6—C17	−173.0 (6)
O6—C20—C21—C22	−89.7 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.11	2.940 (5)	163

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₃₂H₃₀N₂O₈
M_r	570.58
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	7.3646 (7), 8.1772 (8), 13.329 (1)
α, β, γ (°)	97.905 (2), 100.352 (2), 109.296 (2)
V (Å³)	728.33 (12)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.46 × 0.28 × 0.16

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5566, 2808, 1747
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.144, 1.02
No. of reflections	2808
No. of parameters	382
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.21

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2003), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.11	2.940 (5)	163

Symmetry code: (i) x+1, y, z.

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