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The crystal structure of the antihypertensive and cardiovascular protective ramipril {systematic name: 1-[2-(1-ethoxy­carbonyl-3-phenyl­propyl­amino)­propionyl]­octa­hydro­cyclopenta­[b]­pyrrole-2-carboxyl­ic acid}, C23H32N2O5, has been determined. Within the crystal structure, strong hydrogen bonds connect the mol­ecules into chains along the [100] direction. The preferred crystal growth along these chains causes a crystal morphology of very thin needles which previously prevented the crystal structure determination.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801006948/cv6021sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801006948/cv6021Isup2.hkl
Contains datablock I

CCDC reference: 165672

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.064
  • wR factor = 0.085
  • Data-to-parameter ratio = 11.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Red Alert Alert Level A:
DIFF_019 Alert A _diffrn_standards_number is missing Number of standards used in measurement.
Author response: Data was collected with an area detector
DIFF_020  Alert A _diffrn_standards_interval_count and
          _diffrn_standards_interval_time are missing. Number of measurements
          between standards or time (min) between standards.
Author response: Data was collected with an area detector

Amber Alert Alert Level B:
RINTA_01 Alert B The value of Rint is greater than 0.15 Rint given 0.166
Author response: Only small and poorly reflecting needles can be crystallized, but the compound is comercially very important, which might justify the publication, though the quality of the structure determination meets not the usual standards. See _publ_section_exptl_refinement and _publ_section_comment.
THETM_01  Alert B The value of sine(theta_max)/wavelength is less than 0.575
          Calculated sin(theta_max)/wavelength =    0.5568
Author response: See _publ_section_exptl_refinement and _publ_section_comment.

Yellow Alert Alert Level C:
STRVAL_01 From the CIF: _refine_ls_abs_structure_Flack -2.000 From the CIF: _refine_ls_abs_structure_Flack_su 1.900 Alert C Flack parameter is too small General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 23.31 From the CIF: _reflns_number_total 3291 Count of symmetry unique reflns 1937 Completeness (_total/calc) 169.90% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1354 Fraction of Friedel pairs measured 0.699 Are heavy atom types Z>Si present no ALERT: MoKa measured Friedel data cannot be used to determine absolute structure in a light-atom study EXCEPT under VERY special conditions. It is preferred that Friedel data is merged in such cases.
2 Alert Level A = Potentially serious problem
2 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

Ramipril, (I), is an ACE inhibitor, which can dramatically improve cardiovascular outcomes (Hall et al., 1997; Yusuf et al., 2000). The active pharmaceutical ingredient is contained in numerous drugs with trade names such as Delix, Altace, Triace, Triatec, Delmuno, Unimax, Acovil and Vesdil. Crystals of ramipril adopt the morphology of long very thin needles and during drug development in the eighties, all attempts to determine the crystal structure remained unsuccessful. The absolute configuration (all S) was confirmed by structure determinations of derivatives (Paulus, Geiger et al., 1987; Paulus, Henning & Urbach, 1987), taking into account, that L-alanine was one of the educts. In 1987, the last attempt to determine the crystal structure failed, since the collected diffraction data of the largest crystal found (0.7 × 0.05 × 0.03 mm) was too weak. A new data collection on the same crystal applying a rotating anode operated at 50 kV and 120 mA still yielded a data set with reflections observed only up to about 1.0 Å, but the structure was solved with direct methods, immediately.

Ramipril crystallizes in the orthorhombic space group P212121 with one molecule in the asymmetric unit (Fig. 1). Since there are no atoms higher than oxygen present in the crystal structure, it was not possible to reconfirm the absolute configuration (Flack & Bernadinelli, 1999) and the absolute structure with ramipril in ab all-S configuration was chosen for refinement. All bond lengths and angles (Table 1) are in the usual range of values (Orpen et al., 1994). The first five-membered ring (N01, C01–C04) is twisted on C01—C02 and the second five-membered ring (C03–C07) is twisted on C5—C6. A Cremer & Pople puckering analysis (Cremer & Pople, 1975) yields Q = 0.275 Å and ϕ = 61.48°, and Q = 0.4407 Å and ϕ = 121.64°, respectively. Despite of the coexistence of a carboxylic acid group and an amino group, the neutral molecule and not the zwitter ionic tautomer is found in the crystal. The carboxylic acid group adopts the frequently observed synplanar (s-cis) conformation (Leiserowitz, 1976; Gandour, 1981). An intramolecular hydrogen bond between the amino hydrogen H2 and the amido oxygen O03 is formed with contact distances N02···O03 2.829 (5) Å and H2···O03 2.43 (3) Å and an angle N02—H2···O03 114 (3)°. Within the crystal structure, the molecules are connected to chains via strong –COOH···NH– hydrogen bonds between the caboxylic acid groups and the amino groups of adjacent molecules. The molecules within these chains are symmetry related by the 21 screw axis parallel to the crystallographic a axis. These hydrogen-bonded chains account for a preferred crystal growth in [10 0] direction and for the corresponding crystal morphology with the long needle axis coinciding with this direction. The intermolecular hydrogen bond exhibits distances O01···N02i 2.601 (5) Å and H1···N02i 1.58 (6) Å, and an angle O01—H1···N02 168 (4)° [symmetry code: (i) x + 1/2, 1/2 - y, -z]. In addition, a short intermolecular distance C03—H03···O05ii to the carbonyl oxygen of the ester group is found [C03···O5ii 3.388 (6) Å, H03···O05 2.45 Å and C03—H03···O5ii 161°; symmetry code: (ii) 3/2 - x, -y, z + 1/2 which might be discussed as a weak intermolecular C—H···O hydrogen bond (Desiraju, 1996; Desiraju & Steiner, 1998).

The experimentally determined powder diffraction pattern of the sample agrees with the one calculated from the crystal structure model, which proves that the determined crystal structure represents the crystalline phase of the sample.

Experimental top

The sample was recystallized several times from ethanol–diisopropyl ether for further purification. In the final crystallization step, an ethanolic solution, which was almost saturated at 313 K, was slowly cooled to room temperature.

Refinement top

Data was originally collected to 54° 2θ with a SMART 1 K CCD area detector, but reflections were observed only up to about 1 Å/45° 2θ. Refinement was therefore done with data up to 0.9 Å/47° 2θ. All H atoms were found in the electron-density difference map, but most of them were placed in idealized geometry with fixed isotropic displacement parameters. Only the coordinates and isotropic displacement parameters of the H atom of the carboxylic acid group (H1) and of the H atom of the amino group (H2), which are involved in hydrogen bonds, were refined.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT+ (Bruker, 1999); data reduction: SAINT+; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-PC XP (Bruker, 1998); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular structure of ramipril (most H atoms omitted) showing anisotropic displacement ellipsoids at the 20% probability level and the atom-numbering scheme. The dashed lines indicate hydrogen bonds.
1-[2-(1-ethoxycarbonyl-3-phenylpropylamino)propionyl]octahydrocyclopenta[b]- pyrrole-2-carboxylic acid top
Crystal data top
C23H32N2O5Dx = 1.205 Mg m3
Mr = 416.51Melting point: 109°C K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
a = 7.4845 (11) ÅCell parameters from 2316 reflections
b = 13.937 (2) Åθ = 2.4–18.2°
c = 22.012 (3) ŵ = 0.09 mm1
V = 2296.0 (6) Å3T = 293 K
Z = 4Needle, colourless
F(000) = 8960.7 × 0.05 × 0.03 mm
Data collection top
Bruker AXS four-circle
diffractometer
1640 reflections with I > 2σ(I)
Radiation source: rotating anodeRint = 0.166
Graphite monochromatorθmax = 23.3°, θmin = 2.4°
ω scansh = 48
15851 measured reflectionsk = 1515
3291 independent reflectionsl = 2424
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.064H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.085 w = 1/[σ2(Fo2) + (0.0263P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.92(Δ/σ)max < 0.001
3291 reflectionsΔρmax = 0.13 e Å3
279 parametersΔρmin = 0.14 e Å3
0 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 2.0 (19)
Crystal data top
C23H32N2O5V = 2296.0 (6) Å3
Mr = 416.51Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.4845 (11) ŵ = 0.09 mm1
b = 13.937 (2) ÅT = 293 K
c = 22.012 (3) Å0.7 × 0.05 × 0.03 mm
Data collection top
Bruker AXS four-circle
diffractometer
1640 reflections with I > 2σ(I)
15851 measured reflectionsRint = 0.166
3291 independent reflectionsθmax = 23.3°
Refinement top
R[F2 > 2σ(F2)] = 0.064H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.085Δρmax = 0.13 e Å3
S = 0.92Δρmin = 0.14 e Å3
3291 reflectionsAbsolute structure: Flack (1983)
279 parametersAbsolute structure parameter: 2.0 (19)
0 restraints
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
xyzUiso*/Ueq
O010.8534 (4)0.2836 (3)0.11780 (14)0.0676 (10)
H10.939 (7)0.336 (4)0.101 (2)0.109 (19)*
O020.9727 (5)0.1845 (2)0.04956 (14)0.0710 (10)
O030.7016 (4)0.0561 (2)0.00152 (12)0.0675 (10)
O040.8473 (4)0.2369 (2)0.17916 (14)0.0729 (10)
O050.6397 (4)0.1236 (2)0.19571 (14)0.0803 (11)
N010.7448 (5)0.0376 (2)0.08079 (16)0.0547 (10)
N020.5954 (6)0.1032 (3)0.07252 (18)0.0526 (12)
H20.589 (5)0.049 (2)0.0805 (16)0.039 (15)*
C010.7351 (6)0.1286 (3)0.11407 (18)0.0584 (12)
H010.61440.15530.11050.070*
C020.7694 (8)0.0984 (4)0.1801 (2)0.0944 (17)
H0210.83160.14870.20210.113*
H0220.65790.08460.20080.113*
C030.8840 (9)0.0091 (4)0.1756 (2)0.0900 (17)
H030.85150.03580.20800.108*
C040.8450 (7)0.0370 (3)0.1131 (2)0.0692 (15)
H040.77150.09470.11800.083*
C051.0878 (10)0.0224 (5)0.1744 (3)0.119 (2)
H0511.11940.08330.15600.143*
H0521.13660.02010.21520.143*
C061.1574 (8)0.0604 (5)0.1366 (3)0.115 (2)
H0621.27750.04800.12200.138*
H0611.15650.11990.15940.138*
C071.0250 (7)0.0628 (3)0.0852 (2)0.0769 (15)
H0711.02070.12620.06710.092*
H0721.05750.01680.05410.092*
C080.8697 (7)0.2008 (3)0.0902 (2)0.0520 (12)
C090.6838 (5)0.0214 (3)0.0242 (2)0.0515 (13)
C100.5754 (5)0.1012 (3)0.00601 (18)0.0483 (12)
H100.61310.16320.01060.058*
C110.3784 (5)0.0845 (3)0.00971 (18)0.0705 (14)
H1110.34140.02320.00560.106*
H1120.30690.13410.00840.106*
H1130.36350.08590.05300.106*
C120.7651 (6)0.1439 (3)0.09581 (17)0.0468 (11)
H120.78650.20470.07470.056*
C130.7382 (8)0.1659 (4)0.1625 (2)0.0581 (14)
C140.8554 (8)0.2576 (4)0.2443 (2)0.0966 (19)
H1410.87980.32530.25030.116*
H1420.74090.24320.26280.116*
C150.9973 (9)0.1995 (4)0.2738 (2)0.125 (2)
H1511.11010.21280.25480.188*
H1521.00370.21570.31620.188*
H1530.96970.13260.26950.188*
C160.9326 (5)0.0823 (3)0.08925 (17)0.0499 (12)
H1611.03510.11990.10180.060*
H1620.94830.06660.04660.060*
C170.9309 (6)0.0108 (3)0.12562 (19)0.0674 (13)
H1710.83000.04950.11290.081*
H1720.91540.00410.16830.081*
C181.1002 (7)0.0677 (3)0.1175 (2)0.0586 (13)
C191.2530 (9)0.0455 (3)0.14919 (19)0.0693 (14)
H191.25200.00610.17600.083*
C201.4077 (8)0.0979 (5)0.1421 (3)0.0842 (17)
H201.50820.08300.16510.101*
C211.4137 (11)0.1717 (5)0.1014 (3)0.100 (2)
H211.51910.20570.09520.119*
C221.2611 (11)0.1951 (4)0.0696 (3)0.0953 (19)
H221.26320.24620.04250.114*
C231.1063 (8)0.1441 (4)0.0777 (2)0.0825 (16)
H231.00430.16110.05600.099*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O010.080 (3)0.060 (2)0.062 (2)0.0136 (19)0.0148 (19)0.009 (2)
O020.086 (3)0.058 (2)0.069 (2)0.0111 (18)0.025 (2)0.0078 (19)
O030.088 (3)0.0458 (18)0.069 (2)0.0039 (17)0.0168 (17)0.0041 (18)
O040.089 (3)0.079 (2)0.051 (2)0.003 (2)0.005 (2)0.0188 (18)
O050.095 (3)0.099 (3)0.046 (2)0.003 (2)0.0097 (19)0.013 (2)
N010.079 (3)0.046 (2)0.039 (2)0.005 (2)0.006 (2)0.006 (2)
N020.063 (3)0.041 (3)0.054 (3)0.002 (3)0.006 (2)0.010 (2)
C010.085 (4)0.054 (3)0.037 (3)0.011 (3)0.012 (3)0.000 (3)
C020.151 (5)0.081 (4)0.051 (3)0.013 (4)0.012 (4)0.002 (3)
C030.138 (6)0.090 (5)0.042 (3)0.023 (4)0.022 (4)0.020 (3)
C040.082 (4)0.061 (4)0.064 (4)0.011 (3)0.012 (3)0.018 (3)
C050.153 (7)0.118 (5)0.088 (5)0.020 (5)0.069 (5)0.009 (4)
C060.120 (5)0.110 (5)0.114 (5)0.006 (4)0.049 (5)0.038 (4)
C070.084 (4)0.068 (3)0.079 (4)0.004 (3)0.022 (4)0.024 (3)
C080.059 (4)0.054 (3)0.043 (3)0.003 (3)0.007 (3)0.000 (3)
C090.056 (3)0.045 (3)0.053 (3)0.007 (3)0.001 (3)0.013 (3)
C100.059 (3)0.053 (3)0.033 (3)0.007 (3)0.001 (2)0.006 (2)
C110.055 (3)0.083 (3)0.073 (3)0.005 (3)0.006 (3)0.001 (3)
C120.053 (3)0.045 (3)0.043 (3)0.001 (3)0.005 (3)0.010 (2)
C130.071 (4)0.062 (4)0.042 (4)0.020 (3)0.005 (3)0.003 (3)
C140.115 (5)0.113 (5)0.062 (4)0.018 (4)0.010 (4)0.031 (3)
C150.140 (6)0.166 (6)0.069 (4)0.015 (5)0.021 (4)0.003 (4)
C160.053 (3)0.052 (3)0.045 (3)0.007 (3)0.006 (2)0.001 (2)
C170.069 (3)0.069 (3)0.064 (3)0.014 (3)0.010 (3)0.015 (3)
C180.063 (4)0.050 (3)0.062 (4)0.011 (3)0.007 (3)0.024 (3)
C190.079 (4)0.060 (3)0.069 (3)0.014 (4)0.003 (4)0.021 (3)
C200.072 (5)0.077 (4)0.104 (5)0.003 (4)0.002 (4)0.041 (4)
C210.106 (6)0.065 (5)0.128 (6)0.027 (4)0.038 (5)0.035 (4)
C220.110 (6)0.062 (4)0.113 (5)0.021 (5)0.015 (5)0.004 (3)
C230.091 (5)0.069 (4)0.088 (4)0.011 (4)0.002 (4)0.014 (4)
Geometric parameters (Å, º) top
O01—C081.311 (5)C09—C101.529 (5)
O01—H11.04 (6)C10—C111.532 (5)
O02—C081.202 (5)C10—H100.9800
O03—C091.226 (5)C11—H1110.9600
O04—C131.334 (5)C11—H1120.9600
O04—C141.463 (4)C11—H1130.9600
O05—C131.194 (5)C12—C131.513 (5)
N01—C091.347 (4)C12—C161.527 (5)
N01—C011.466 (4)C12—H120.9800
N01—C041.467 (5)C14—C151.485 (6)
N02—C101.472 (5)C14—H1410.9700
N02—C121.482 (5)C14—H1420.9700
N02—H20.77 (3)C15—H1510.9600
C01—C081.518 (5)C15—H1520.9600
C01—C021.534 (5)C15—H1530.9600
C01—H010.9800C16—C171.524 (4)
C02—C031.515 (6)C16—H1610.9700
C02—H0210.9700C16—H1620.9700
C02—H0220.9700C17—C181.506 (5)
C03—C051.537 (6)C17—H1710.9700
C03—C041.546 (6)C17—H1720.9700
C03—H030.9800C18—C191.374 (6)
C04—C071.523 (6)C18—C231.381 (6)
C04—H040.9800C19—C201.378 (6)
C05—C061.513 (6)C19—H190.9300
C05—H0510.9700C20—C211.365 (7)
C05—H0520.9700C20—H200.9300
C06—C071.505 (6)C21—C221.378 (7)
C06—H0620.9700C21—H210.9300
C06—H0610.9700C22—C231.371 (7)
C07—H0710.9700C22—H220.9300
C07—H0720.9700C23—H230.9300
C08—O01—H1114 (2)C09—C10—H10109.1
C13—O04—C14116.1 (4)C11—C10—H10109.1
C09—N01—C01126.3 (4)C10—C11—H111109.5
C09—N01—C04120.2 (4)C10—C11—H112109.5
C01—N01—C04113.4 (4)H111—C11—H112109.5
C10—N02—C12116.0 (3)C10—C11—H113109.5
C10—N02—H2102 (3)H111—C11—H113109.5
C12—N02—H2110 (3)H112—C11—H113109.5
N01—C01—C08111.5 (4)N02—C12—C13107.4 (4)
N01—C01—C02103.2 (3)N02—C12—C16117.1 (3)
C08—C01—C02113.5 (4)C13—C12—C16108.3 (3)
N01—C01—H01109.5N02—C12—H12107.9
C08—C01—H01109.5C13—C12—H12107.9
C02—C01—H01109.5C16—C12—H12107.9
C03—C02—C01104.9 (4)O05—C13—O04125.2 (5)
C03—C02—H021110.8O05—C13—C12125.2 (5)
C01—C02—H021110.8O04—C13—C12109.6 (5)
C03—C02—H022110.8O04—C14—C15110.5 (4)
C01—C02—H022110.8O04—C14—H141109.5
H021—C02—H022108.8C15—C14—H141109.5
C02—C03—C05117.6 (5)O04—C14—H142109.5
C02—C03—C04107.1 (4)C15—C14—H142109.5
C05—C03—C04102.8 (5)H141—C14—H142108.1
C02—C03—H03109.6C14—C15—H151109.5
C05—C03—H03109.6C14—C15—H152109.5
C04—C03—H03109.6H151—C15—H152109.5
N01—C04—C07115.1 (4)C14—C15—H153109.5
N01—C04—C03103.5 (4)H151—C15—H153109.5
C07—C04—C03106.9 (4)H152—C15—H153109.5
N01—C04—H04110.4C17—C16—C12115.0 (3)
C07—C04—H04110.4C17—C16—H161108.5
C03—C04—H04110.4C12—C16—H161108.5
C06—C05—C03105.0 (5)C17—C16—H162108.5
C06—C05—H051110.7C12—C16—H162108.5
C03—C05—H051110.7H161—C16—H162107.5
C06—C05—H052110.7C18—C17—C16112.3 (3)
C03—C05—H052110.7C18—C17—H171109.1
H051—C05—H052108.8C16—C17—H171109.1
C07—C06—C05101.7 (5)C18—C17—H172109.1
C07—C06—H062111.4C16—C17—H172109.1
C05—C06—H062111.4H171—C17—H172107.9
C07—C06—H061111.4C19—C18—C23117.9 (5)
C05—C06—H061111.4C19—C18—C17121.5 (5)
H062—C06—H061109.3C23—C18—C17120.6 (6)
C06—C07—C04105.9 (4)C18—C19—C20121.5 (5)
C06—C07—H071110.6C18—C19—H19119.2
C04—C07—H071110.6C20—C19—H19119.2
C06—C07—H072110.6C21—C20—C19120.1 (6)
C04—C07—H072110.6C21—C20—H20120.0
H071—C07—H072108.7C19—C20—H20120.0
O02—C08—O01124.8 (4)C20—C21—C22119.0 (7)
O02—C08—C01124.0 (5)C20—C21—H21120.5
O01—C08—C01111.2 (4)C22—C21—H21120.5
O03—C09—N01122.6 (4)C23—C22—C21120.8 (6)
O03—C09—C10119.9 (4)C23—C22—H22119.6
N01—C09—C10117.3 (4)C21—C22—H22119.6
N02—C10—C09113.1 (4)C22—C23—C18120.6 (6)
N02—C10—C11109.0 (3)C22—C23—H23119.7
C09—C10—C11107.6 (3)C18—C23—H23119.7
N02—C10—H10109.1
C09—N01—C01—C0874.4 (5)C04—N01—C09—C10178.2 (3)
C04—N01—C01—C08100.3 (4)C12—N02—C10—C0976.2 (4)
C09—N01—C01—C02163.4 (4)C12—N02—C10—C11164.2 (3)
C04—N01—C01—C0221.9 (5)O03—C09—C10—N0235.6 (5)
N01—C01—C02—C0328.0 (5)N01—C09—C10—N02149.4 (4)
C08—C01—C02—C0392.8 (5)O03—C09—C10—C1184.7 (5)
C01—C02—C03—C0589.8 (5)N01—C09—C10—C1190.3 (4)
C01—C02—C03—C0425.2 (5)C10—N02—C12—C13163.9 (4)
C09—N01—C04—C0765.4 (5)C10—N02—C12—C1674.0 (5)
C01—N01—C04—C07109.7 (4)C14—O04—C13—O055.5 (6)
C09—N01—C04—C03178.5 (4)C14—O04—C13—C12171.8 (4)
C01—N01—C04—C036.4 (5)N02—C12—C13—O0529.5 (6)
C02—C03—C04—N0112.1 (5)C16—C12—C13—O0597.8 (5)
C05—C03—C04—N01112.5 (5)N02—C12—C13—O04153.3 (3)
C02—C03—C04—C07134.0 (4)C16—C12—C13—O0479.4 (4)
C05—C03—C04—C079.4 (5)C13—O04—C14—C1589.9 (5)
C02—C03—C05—C06149.4 (4)N02—C12—C16—C1764.8 (4)
C04—C03—C05—C0632.1 (5)C13—C12—C16—C1756.8 (5)
C03—C05—C06—C0742.6 (5)C12—C16—C17—C18179.5 (4)
C05—C06—C07—C0436.1 (5)C16—C17—C18—C1980.5 (5)
N01—C04—C07—C06130.8 (4)C16—C17—C18—C2399.3 (5)
C03—C04—C07—C0616.6 (5)C23—C18—C19—C200.6 (6)
N01—C01—C08—O020.9 (6)C17—C18—C19—C20179.6 (4)
C02—C01—C08—O02115.1 (5)C18—C19—C20—C212.3 (7)
N01—C01—C08—O01176.4 (4)C19—C20—C21—C222.7 (8)
C02—C01—C08—O0167.6 (5)C20—C21—C22—C231.4 (9)
C01—N01—C09—O03177.7 (4)C21—C22—C23—C180.3 (8)
C04—N01—C09—O033.3 (6)C19—C18—C23—C220.7 (7)
C01—N01—C09—C107.4 (6)C17—C18—C23—C22179.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O01—H1···N02i1.04 (6)1.58 (6)2.601 (5)168 (4)
N02—H2···O030.78 (3)2.43 (3)2.829 (5)114 (3)
C03—H03···O05ii0.982.453.388 (6)161
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x+3/2, y, z+1/2.

Experimental details

Crystal data
Chemical formulaC23H32N2O5
Mr416.51
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)7.4845 (11), 13.937 (2), 22.012 (3)
V3)2296.0 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.7 × 0.05 × 0.03
Data collection
DiffractometerBruker AXS four-circle
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
15851, 3291, 1640
Rint0.166
θmax (°)23.3
(sin θ/λ)max1)0.557
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.064, 0.085, 0.92
No. of reflections3291
No. of parameters279
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.13, 0.14
Absolute structureFlack (1983)
Absolute structure parameter2.0 (19)

Computer programs: SMART (Bruker, 1999), SAINT+ (Bruker, 1999), SAINT+, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL-PC XP (Bruker, 1998), SHELXL97.

Selected geometric parameters (Å, º) top
O01—C081.311 (5)C03—C041.546 (6)
O01—H11.04 (6)C04—C071.523 (6)
O02—C081.202 (5)C05—C061.513 (6)
O03—C091.226 (5)C06—C071.505 (6)
O04—C131.334 (5)C09—C101.529 (5)
O04—C141.463 (4)C10—C111.532 (5)
O05—C131.194 (5)C12—C131.513 (5)
N01—C091.347 (4)C12—C161.527 (5)
N01—C011.466 (4)C14—C151.485 (6)
N01—C041.467 (5)C16—C171.524 (4)
N02—C101.472 (5)C17—C181.506 (5)
N02—C121.482 (5)C18—C191.374 (6)
N02—H20.77 (3)C18—C231.381 (6)
C01—C081.518 (5)C19—C201.378 (6)
C01—C021.534 (5)C20—C211.365 (7)
C02—C031.515 (6)C21—C221.378 (7)
C03—C051.537 (6)C22—C231.371 (7)
C13—O04—C14116.1 (4)O03—C09—C10119.9 (4)
C09—N01—C01126.3 (4)N01—C09—C10117.3 (4)
C09—N01—C04120.2 (4)N02—C10—C09113.1 (4)
C01—N01—C04113.4 (4)N02—C10—C11109.0 (3)
C10—N02—C12116.0 (3)C09—C10—C11107.6 (3)
N01—C01—C08111.5 (4)N02—C12—C13107.4 (4)
N01—C01—C02103.2 (3)N02—C12—C16117.1 (3)
C08—C01—C02113.5 (4)C13—C12—C16108.3 (3)
C03—C02—C01104.9 (4)O05—C13—O04125.2 (5)
C02—C03—C05117.6 (5)O05—C13—C12125.2 (5)
C02—C03—C04107.1 (4)O04—C13—C12109.6 (5)
C05—C03—C04102.8 (5)O04—C14—C15110.5 (4)
N01—C04—C07115.1 (4)C18—C17—C16112.3 (3)
N01—C04—C03103.5 (4)C19—C18—C23117.9 (5)
C07—C04—C03106.9 (4)C19—C18—C17121.5 (5)
C06—C05—C03105.0 (5)C23—C18—C17120.6 (6)
C07—C06—C05101.7 (5)C18—C19—C20121.5 (5)
C06—C07—C04105.9 (4)C21—C20—C19120.1 (6)
O02—C08—O01124.8 (4)C20—C21—C22119.0 (7)
O02—C08—C01124.0 (5)C23—C22—C21120.8 (6)
O01—C08—C01111.2 (4)C22—C23—C18120.6 (6)
O03—C09—N01122.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O01—H1···N02i1.04 (6)1.58 (6)2.601 (5)168 (4)
N02—H2···O030.78 (3)2.43 (3)2.829 (5)114 (3)
C03—H03···O05ii0.982.453.388 (6)161
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x+3/2, y, z+1/2.
 

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