organic compounds
Ampicillin trihydrate from synchrotron powder diffraction data
aUniversity Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, England, bCambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, England, and cDepartment of Physics and Astronomy, SUNY at Stony Brook, Stony Brook, NY 11794-3800, USA
*Correspondence e-mail: jb442@cam.ac.uk
The D(−)-α-aminophenylacetamido]penicillanic acid trihydrate}, C16H19N3O4S·3H2O, a broad-spectrum β-lactam antibiotic of the aminopenicillin type, has been determined from synchrotron X-ray powder diffraction data. The three water molecules form an infinite hydrogen-bonded chain through the with hydrogen bonds to the NH3+, COO−, C=O and NH groups of the ampicillin molecules.
of ampicillin trihydrate {systematic name: 6-[Comment
The title compound, (I), has been used as a broad-spectrum antibiotic since 1961. The was reported in 1968 (James et al., 1968), but no atomic coordinates were given in the paper or deposited. Boles et al. (1978) published the of a related compound, amoxycillin trihydrate. They apparently had access to the atomic coordinates of the of compound (I), because in their paper they show that the two crystal structures are isostructural. However, the atomic coordinates of the title compound have not been published to date. We report the here, determined from synchrotron X-ray powder diffraction.
The structural model of compound (I) obtained in the present work (Fig. 1a) is both chemically reasonable and in accord with the figures given by James et al. (1968). Selected geometric parameters are given in Table 1. We note, however, that the hydrogen bond O26′′′⋯O25′′′ in their Fig. 1, which appears to link four water molecules together into a closed tetramer, is spurious, and instead should have formed a chain (Fig. 1b). Both the pattern of hydrogen bonding, and the positions of the H atoms of the water molecules in the structure, are chemically sensible and compare well with those from the of the isostructural amoxycillin trihydrate (Boles et al., 1978). Details of the O—H⋯O and N—H⋯O hydrogen bonds are given in Table 2 and Fig. 1.
Experimental
The sample of compound (I) was a gift from Setauket Pharmacy, Setauket, New York, USA, in the form of a gelatin capsule of the compound. Some of the contents were loaded into a thin-walled glass capillary of 1.5 mm nominal diameter. Any excipients that might have been present were not crystalline. A diffraction pattern was collected at the X3B1 beamline of the National Synchrotron Light Source, Brookhaven National Laboratory. The wavelength of 0.7003 (1) Å was selected by a double Si(111) monochromator and the diffracted beam analyzed by a Ge(111) crystal before the detector. The beam on the sample had dimensions 2 mm × 8 mm. Data were collected from 2θ = 3–41.6° in steps of 0.005°, with counting time increasing quadratically from 1–8 s per point. The incident beam was monitored by an ion chamber, which was used to normalize the data for decay and fluctuations of the intensity.
Crystal data
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Data collection
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Refinement
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The starting model for DASH (David et al., 2004). For the structure solution, the data were truncated at 22.855° in 2θ, corresponding to a real-space resolution of 1.767 Å. The background was subtracted with a Bayesian high-pass filter (David & Sivia, 2001). Peak positions for indexing were obtained by fitting with an asymmetry-corrected Voigt function, followed by indexing with the program DICVOL (Boultif & Louer, 1991). An orthorhombic and several monoclinic unit cells were obtained. However, all the monoclinic unit cells were pseudo-orthorhombic with nearly the same parameters as the orthorhombic cell, indicating that the orthorhombic is the correct one. The figures of merit given by DICVOL were M(20) = 62.1 and F(20) = 337.1 (0.0014, 42). The reported for the single-crystal structure, P212121, gave an excellent Pawley fit.
was obtained by solving the from the powder diffraction pattern. This also provided an independent check that the published is correct. However, with the being known, its determination from the powder pattern is mainly academic. The was determined with the programSimulated annealing was used to solve the from the powder pattern in The starting molecular geometry was taken from the anhydrate (Boles & Girven, 1976), entry AMCILL in the Cambridge Structural Database (Allen, 2002). The molecule is a zwitterion, in agreement with the single-crystal study. Because H atoms do not contribute significantly to the powder diffraction pattern, due to their low X-ray scattering power, they were ignored during the structure solution process. Hence, the water molecule can be reduced to an O atom, which reduces its number of from six to three. The molecule has five flexible torsion angles, which, when combined with the three water molecules, give a total of 20 In ten simulated annealing runs, the correct was found twice, with a profile χ2 = 81.7, 11 times the Pawley χ2. The next-best had a profile χ2 = 240. The low success rate and high profile χ2 are caused by the high R factor of 10.6% of the of AMCILL from which the starting model was taken; when the structure solution was repeated with a better starting model (obtained from against the powder data), the correct structure was found four times in ten runs, with a profile χ2 = 20, less than three times the Pawley χ2.
of compound (I)The background subtraction, DASH.
indexing, Pawley and simulated-annealing algorithms used are as implemented in the programFor the ), H atoms were included in the initial model in calculated positions. Bond lengths, bond angles and planar groupings were subjected to suitable constraints, including bonds to H atoms. Data were included to 41.42° in 2θ, corresponding to a real-space resolution of 0.99 Å. The was not particularly sensitive to the position of the water H atoms and these were included in calculated positions, with the water molecules being fixed in position for the final cycles. The proceeded smoothly to reach a minimum characterized by an excellent fit to the diffraction profile (χ2 = 5.637, Rp = 0.0296, Rwp = 0.0296 and RBragg = 0.0295).
(Fig. 2Data collection: local software; cell GSAS (Larson & Von Dreele, 2000); data reduction: local software; program(s) used to solve structure: DASH (David et al., 2004); program(s) used to refine structure: GSAS; molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.
Supporting information
https://doi.org/10.1107/S1600536806001371/su2001sup1.cif
contains datablocks global, I. DOI:Rietveld powder data: contains datablock _____________________publ. DOI: https://doi.org/10.1107/S1600536806001371/su2001Isup2.rtv
Structure factors: contains datablock _____________________publ. DOI: https://doi.org/10.1107/S1600536806001371/su2001Isup3.hkl
Data collection: local software; cell
GSAS (Larson & Von Dreele, 2000); data reduction: local software; program(s) used to solve structure: DASH (David et al., 2004); program(s) used to refine structure: GSAS; molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.C16H19N3O4S·3H2O | Z = 4 |
Mr = 403.06 | Dx = 1.367 Mg m−3 |
Orthorhombic, P212121 | Synchrotron radiation, λ = 0.7003 Å |
a = 15.52275 (16) Å | T = 290 K |
b = 18.9256 (3) Å | Particle morphology: powder |
c = 6.67375 (8) Å | white |
V = 1960.60 (3) Å3 | cylinder, 0.7 × 20 mm |
Diffractometer x3b1 | Data collection mode: transmission |
Radiation source: Brookhaven NSLS | Scan method: step |
Specimen mounting: Lindemann glass capillary |
Least-squares matrix: full | 143 parameters |
Rp = 0.025 | 136 restraints |
Rwp = 0.030 | H-atom parameters constrained |
Rexp = 0.013 | Weighting scheme based on measured s.u.'s |
R(F2) = 0.02950 | (Δ/σ)max = 0.03 |
Excluded region(s): none | Background function: GSAS Background function number 1 with 9 terms. Shifted Chebyshev function of 1st kind 1: 2261.50 2: -239.085 3: 47.0827 4: -155.949 5: 139.395 6: -237.334 7: 231.040 8: -74.9779 9: 19.4239 10: -0.402815 |
Profile function: CW Profile function number 3 with 19 terms Pseudovoigt profile coefficients as parameterized in Thompson et al. (1987). Asymmetry correction of Finger et al. (1994). #1(GU) = 0.000 #2(GV) = 0.000 #3(GW) = 0.000 #4(GP) = 0.000 #5(LX) = 2.213 #6(LY) = 33.715 #7(S/L) = 0.0130 #8(H/L) = 0.0130 #9(trns) = 0.00 #10(shft)= 0.0832 #11(stec)= 0.00 #12(ptec)= 0.00 #13(sfec)= 0.00 #14(L11) = 0.000 #15(L22) = 0.000 #16(L33) = 0.000 #17(L12) = 0.000 #18(L13) = 0.000 #19(L23) = 0.000 Peak tails are ignored where the intensity is below 0.0010 times the peak Aniso. broadening axis 0.0 0.0 1.0 |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
x | y | z | Uiso*/Ueq | ||
S10 | 0.33689 (14) | 0.46707 (11) | 0.2754 (3) | 0.0350 (4)* | |
O17 | 0.5429 (2) | 0.3613 (2) | 0.5525 (7) | 0.0350 (4)* | |
O21 | 0.3263 (3) | 0.2430 (2) | 0.6113 (6) | 0.0350 (4)* | |
O22 | 0.2965 (3) | 0.2156 (2) | 0.2943 (6) | 0.0350 (4)* | |
O25 | 0.5385 (3) | 0.5837 (2) | 0.7961 (5) | 0.0350 (4)* | |
N13 | 0.3923 (2) | 0.37247 (18) | 0.5272 (5) | 0.0350 (4)* | |
N23 | 0.4964 (3) | 0.5225 (2) | 0.5209 (5) | 0.0350 (4)* | |
N27 | 0.6573 (3) | 0.6581 (2) | 0.5579 (6) | 0.0350 (4)* | |
C11 | 0.2977 (2) | 0.37521 (15) | 0.2374 (5) | 0.0350 (4)* | |
C12 | 0.3623 (2) | 0.32784 (17) | 0.3604 (6) | 0.0350 (4)* | |
C14 | 0.3598 (2) | 0.4474 (2) | 0.5333 (4) | 0.0350 (4)* | |
C15 | 0.4496 (2) | 0.46826 (18) | 0.6238 (5) | 0.0350 (4)* | |
C16 | 0.4759 (2) | 0.39222 (19) | 0.5728 (8) | 0.0350 (4)* | |
C18 | 0.2064 (3) | 0.3683 (3) | 0.3136 (8) | 0.0350 (4)* | |
C19 | 0.3001 (3) | 0.3604 (3) | 0.0177 (6) | 0.0350 (4)* | |
C20 | 0.3239 (4) | 0.2563 (2) | 0.4322 (6) | 0.0350 (4)* | |
C24 | 0.5369 (4) | 0.5759 (3) | 0.6158 (5) | 0.0350 (4)* | |
C26 | 0.5768 (2) | 0.6298 (2) | 0.4722 (5) | 0.0350 (4)* | |
C28 | 0.5114 (3) | 0.6874 (3) | 0.4222 (6) | 0.0350 (4)* | |
C29 | 0.4704 (4) | 0.6867 (3) | 0.2375 (7) | 0.0350 (4)* | |
C30 | 0.4035 (3) | 0.7333 (3) | 0.2002 (7) | 0.0350 (4)* | |
C31 | 0.3851 (4) | 0.7862 (3) | 0.3350 (8) | 0.0350 (4)* | |
C32 | 0.4208 (4) | 0.7839 (3) | 0.5249 (7) | 0.0350 (4)* | |
C33 | 0.4853 (4) | 0.7355 (3) | 0.5675 (6) | 0.0350 (4)* | |
O1 | 0.55980 | 0.49350 | 0.11790 | 0.0350 (4)* | |
O4 | 0.74455 | 0.45750 | 0.19890 | 0.0350 (4)* | |
O7 | 0.71633 | 0.40465 | 0.58470 | 0.0350 (4)* | |
H34 | 0.4160 (4) | 0.3174 (3) | 0.2832 (9) | 0.0350 (4)* | |
H35 | 0.3068 (3) | 0.4564 (4) | 0.6142 (8) | 0.0350 (4)* | |
H36 | 0.4413 (5) | 0.4787 (4) | 0.7695 (7) | 0.0350 (4)* | |
H37 | 0.5926 (5) | 0.6037 (4) | 0.3330 (8) | 0.0350 (4)* | |
H38 | 0.6990 (11) | 0.6186 (5) | 0.581 (6) | 0.0350 (4)* | |
H39 | 0.6446 (7) | 0.682 (2) | 0.688 (3) | 0.0350 (4)* | |
H40 | 0.6835 (16) | 0.6927 (18) | 0.463 (3) | 0.0350 (4)* | |
H41 | 0.4940 (15) | 0.6530 (13) | 0.1193 (16) | 0.0350 (4)* | |
H42 | 0.3735 (13) | 0.7338 (9) | 0.0544 (16) | 0.0350 (4)* | |
H43 | 0.3981 (15) | 0.8194 (12) | 0.6399 (17) | 0.0350 (4)* | |
H44 | 0.5112 (14) | 0.7321 (11) | 0.7174 (14) | 0.0350 (4)* | |
H45 | 0.1765 (10) | 0.4198 (5) | 0.317 (6) | 0.0350 (4)* | |
H46 | 0.1705 (9) | 0.3342 (18) | 0.214 (4) | 0.0350 (4)* | |
H47 | 0.2068 (5) | 0.346 (2) | 0.463 (3) | 0.0350 (4)* | |
H48 | 0.3658 (5) | 0.364 (2) | −0.0353 (16) | 0.0350 (4)* | |
H49 | 0.275 (2) | 0.3082 (8) | −0.0102 (13) | 0.0350 (4)* | |
H50 | 0.261 (2) | 0.3986 (13) | −0.0597 (12) | 0.0350 (4)* | |
H51 | 0.503 (3) | 0.5188 (16) | 0.3719 (11) | 0.0350 (4)* | |
H52 | 0.3394 (16) | 0.8272 (10) | 0.297 (2) | 0.0350 (4)* | |
H2 | 0.55279 | 0.52556 | 1.00373 | 0.0350 (4)* | |
H3 | 0.62022 | 0.48173 | 0.14439 | 0.0350 (4)* | |
H5 | 0.75832 | 0.50601 | 0.15871 | 0.0350 (4)* | |
H6 | 0.73466 | 0.43898 | 0.33409 | 0.0350 (4)* | |
H8 | 0.65604 | 0.38978 | 0.57372 | 0.0350 (4)* | |
H9 | 0.74556 | 0.36129 | 0.62735 | 0.0350 (4)* |
S10—C11 | 1.859 (4) | C14—C15 | 1.570 (4) |
S10—C14 | 1.797 (3) | C15—C16 | 1.534 (5) |
O17—C16 | 1.201 (5) | C24—C26 | 1.531 (6) |
O21—C20 | 1.222 (6) | C26—C28 | 1.527 (6) |
O22—C20 | 1.273 (6) | C28—C29 | 1.387 (7) |
O25—C24 | 1.213 (5) | C28—C33 | 1.390 (7) |
O1—H3 | 0.9800 | C29—C30 | 1.385 (8) |
O1—H2i | 0.9800 | C30—C31 | 1.376 (8) |
O4—H5 | 0.9800 | C31—C32 | 1.384 (7) |
O4—H6 | 0.9800 | C32—C33 | 1.387 (8) |
O7—H9 | 0.9800 | C12—H34 | 1.000 (7) |
O7—H8 | 0.9800 | C14—H35 | 0.999 (6) |
N13—C12 | 1.473 (5) | C15—H36 | 1.001 (6) |
N13—C14 | 1.506 (5) | C18—H47 | 1.08 (2) |
N13—C16 | 1.384 (5) | C18—H45 | 1.080 (12) |
N23—C15 | 1.433 (5) | C18—H46 | 1.08 (3) |
N23—C24 | 1.348 (7) | C19—H49 | 1.078 (18) |
N27—C26 | 1.475 (6) | C19—H48 | 1.082 (10) |
N23—H51 | 1.002 (10) | C19—H50 | 1.08 (2) |
N27—H39 | 1.00 (3) | C26—H37 | 1.080 (7) |
N27—H38 | 1.001 (15) | C29—H41 | 1.079 (19) |
N27—H40 | 1.00 (3) | C30—H42 | 1.079 (14) |
C11—C18 | 1.511 (6) | C31—H52 | 1.08 (2) |
C11—C12 | 1.576 (5) | C32—H43 | 1.079 (19) |
C11—C19 | 1.493 (5) | C33—H44 | 1.080 (13) |
C12—C20 | 1.555 (5) | ||
S10···N13 | 2.602 (4) | H2···H36 | 2.5000 |
S10···N23 | 3.149 (5) | H2···H51x | 2.5800 |
S10···H51 | 2.83 (4) | H2···H3x | 1.6300 |
S10···H35ii | 2.869 (6) | H2···O25 | 1.7800 |
S10···H50iii | 3.16 (2) | H2···C24 | 2.7700 |
O1···O4 | 2.9968 | H3···O4 | 2.0200 |
O1···O25i | 2.7633 | H3···H51 | 2.4700 |
O1···N23 | 2.9161 | H3···H5 | 2.1900 |
O4···N27iv | 2.8272 | H3···H6 | 2.3300 |
O4···O7iv | 2.7850 | H5···O7iv | 1.8000 |
O4···O1 | 2.9968 | H5···H6iv | 2.4100 |
O4···O7 | 2.7967 | H5···H9iv | 2.5200 |
O7···O17 | 2.8225 | H5···H38iv | 2.5000 |
O7···O4 | 2.7967 | H5···H3 | 2.1900 |
O7···O4v | 2.7850 | H5···H8iv | 2.4500 |
O7···O22vi | 2.7166 | H6···O7 | 1.8200 |
O17···N23 | 3.142 (5) | H6···H3 | 2.3300 |
O17···C31vii | 3.156 (7) | H6···H9 | 2.4500 |
O17···C30vii | 3.067 (7) | H6···H5v | 2.4100 |
O17···O7 | 2.8225 | H6···H8 | 2.2200 |
O17···C32viii | 3.228 (7) | H6···H38iv | 2.2600 |
O21···N13 | 2.715 (5) | H6···H52vii | 2.5600 |
O21···N27viii | 2.742 (6) | H8···O17 | 1.8400 |
O22···C26vii | 3.109 (5) | H8···H43viii | 2.4800 |
O22···O7ix | 2.7166 | H8···C16 | 2.8000 |
O22···C19 | 3.305 (6) | H8···H6 | 2.2200 |
O22···C28vii | 3.356 (6) | H8···H5v | 2.4500 |
O22···C18 | 3.213 (7) | H9···H6 | 2.4500 |
O22···N27vii | 2.688 (6) | H9···H5v | 2.5200 |
O25···C33 | 3.356 (7) | H9···O21vi | 2.8300 |
O25···N27 | 2.813 (6) | H9···C20vi | 2.5700 |
O25···O1x | 2.7633 | H9···O22vi | 1.7400 |
O1···H51 | 1.9700 | H34···H48 | 2.430 (18) |
O1···H37 | 2.5800 | H34···O17 | 2.793 (7) |
O4···H52vii | 2.7900 | H34···C28vii | 3.034 (8) |
O4···H38iv | 1.8600 | H34···C29vii | 3.041 (8) |
O4···H3 | 2.0200 | H35···C18 | 3.039 (8) |
O7···H6 | 1.8200 | H35···S10iii | 2.869 (6) |
O7···H5v | 1.8000 | H35···H50x | 2.537 (16) |
O17···H8 | 1.8400 | H36···H2 | 2.5000 |
O17···H42vii | 2.831 (18) | H36···O25 | 2.501 (9) |
O17···H34 | 2.793 (7) | H37···H51 | 2.14 (4) |
O17···H43viii | 2.384 (16) | H37···O1 | 2.5800 |
O21···H44viii | 2.78 (2) | H37···H41 | 2.29 (2) |
O21···H39viii | 1.83 (3) | H37···O22xi | 2.858 (9) |
O21···H9ix | 2.8300 | H38···H52xiii | 2.54 (3) |
O21···H47 | 2.87 (3) | H38···H5v | 2.5000 |
O22···H37vii | 2.858 (9) | H38···H6v | 2.2600 |
O22···H40vii | 1.80 (2) | H38···O4v | 1.8600 |
O22···H9ix | 1.7400 | H39···O25 | 2.59 (3) |
O22···H49 | 2.704 (13) | H39···C33 | 2.790 (19) |
O25···H36 | 2.501 (9) | H39···H44 | 2.29 (3) |
O25···H39 | 2.59 (3) | H39···O21xii | 1.83 (3) |
O25···H41x | 2.617 (17) | H39···C20xii | 2.94 (3) |
O25···H44 | 2.89 (2) | H40···H49xi | 2.30 (4) |
O25···H2 | 1.7800 | H40···O22xi | 1.80 (2) |
N13···S10 | 2.602 (4) | H40···C20xi | 2.90 (2) |
N13···O21 | 2.715 (5) | H41···O25i | 2.617 (17) |
N13···N23 | 3.267 (5) | H41···H37 | 2.29 (2) |
N23···O17 | 3.142 (5) | H42···C18ii | 2.803 (17) |
N23···O1 | 2.9161 | H42···O17xi | 2.831 (18) |
N23···S10 | 3.149 (5) | H42···H47ii | 2.05 (3) |
N23···N13 | 3.267 (5) | H43···C16xii | 3.07 (2) |
N27···O4v | 2.8272 | H43···H8xii | 2.4800 |
N27···O22xi | 2.688 (6) | H43···O17xii | 2.384 (16) |
N27···O25 | 2.813 (6) | H44···C24 | 3.06 (2) |
N27···O21xii | 2.742 (6) | H44···O25 | 2.89 (2) |
N27···H44 | 2.87 (2) | H44···N27 | 2.87 (2) |
C18···O22 | 3.213 (7) | H44···O21xii | 2.78 (2) |
C19···O22 | 3.305 (6) | H44···H39 | 2.29 (3) |
C26···O22xi | 3.109 (5) | H46···C32ii | 2.93 (3) |
C28···O22xi | 3.356 (6) | H46···H49 | 2.26 (3) |
C30···O17xi | 3.067 (7) | H46···C33ii | 2.92 (2) |
C31···O17xi | 3.156 (7) | H47···C14 | 3.09 (2) |
C32···O17xii | 3.228 (7) | H47···O21 | 2.87 (3) |
C33···O25 | 3.356 (7) | H47···H42iii | 2.05 (3) |
C14···H47 | 3.09 (2) | H47···C30iii | 2.77 (2) |
C16···H43viii | 3.07 (2) | H47···C20 | 2.50 (3) |
C16···H8 | 2.8000 | H48···H34 | 2.430 (18) |
C18···H42iii | 2.803 (17) | H49···H40vii | 2.30 (4) |
C18···H35 | 3.039 (8) | H49···H46 | 2.26 (3) |
C20···H47 | 2.50 (3) | H49···O22 | 2.704 (13) |
C20···H9ix | 2.5700 | H50···S10ii | 3.16 (3) |
C20···H39viii | 2.94 (3) | H50···H35i | 2.537 (16) |
C20···H40vii | 2.90 (2) | H51···S10 | 2.83 (4) |
C24···H2 | 2.7700 | H51···O1 | 1.9700 |
C24···H44 | 3.06 (2) | H51···H2i | 2.5800 |
C28···H34xi | 3.034 (8) | H51···H3 | 2.4700 |
C29···H34xi | 3.041 (8) | H51···H37 | 2.14 (4) |
C30···H47ii | 2.77 (2) | H52···O4xi | 2.7900 |
C32···H46iii | 2.93 (3) | H52···H6xi | 2.5600 |
C33···H39 | 2.790 (19) | H52···H38xiv | 2.54 (3) |
C33···H46iii | 2.92 (2) | ||
C11—S10—C14 | 90.10 (18) | C26—C28—C33 | 120.6 (4) |
H2i—O1—H3 | 113.00 | C29—C28—C33 | 119.5 (5) |
H5—O4—H6 | 128.00 | C26—C28—C29 | 119.5 (4) |
H8—O7—H9 | 103.00 | C28—C29—C30 | 119.8 (5) |
C12—N13—C14 | 117.0 (3) | C29—C30—C31 | 120.1 (5) |
C12—N13—C16 | 128.1 (3) | C30—C31—C32 | 119.5 (5) |
C14—N13—C16 | 93.1 (3) | C31—C32—C33 | 119.9 (5) |
C15—N23—C24 | 123.3 (3) | C28—C33—C32 | 120.0 (4) |
C24—N23—H51 | 118 (2) | N13—C12—H34 | 103.8 (4) |
C15—N23—H51 | 119 (2) | C11—C12—H34 | 112.0 (5) |
H38—N27—H40 | 109 (2) | C20—C12—H34 | 107.8 (5) |
H38—N27—H39 | 109 (3) | C15—C14—H35 | 118.7 (4) |
C26—N27—H38 | 109.7 (11) | N13—C14—H35 | 116.8 (5) |
C26—N27—H40 | 109.7 (14) | S10—C14—H35 | 108.6 (4) |
H39—N27—H40 | 110 (2) | C16—C15—H36 | 115.8 (5) |
C26—N27—H39 | 109.5 (9) | C14—C15—H36 | 108.0 (5) |
S10—C11—C19 | 107.5 (3) | N23—C15—H36 | 112.9 (5) |
C12—C11—C18 | 111.9 (3) | C11—C18—H45 | 109.4 (11) |
S10—C11—C12 | 104.6 (2) | C11—C18—H46 | 109.2 (11) |
C12—C11—C19 | 112.9 (3) | C11—C18—H47 | 109.8 (6) |
C18—C11—C19 | 109.7 (3) | H46—C18—H47 | 110 (2) |
S10—C11—C18 | 110.0 (3) | H45—C18—H46 | 109 (2) |
C11—C12—C20 | 114.3 (3) | H45—C18—H47 | 110 (3) |
N13—C12—C11 | 105.6 (3) | C11—C19—H48 | 109.4 (8) |
N13—C12—C20 | 112.8 (3) | C11—C19—H49 | 109.4 (6) |
N13—C14—C15 | 87.1 (2) | C11—C19—H50 | 109.3 (9) |
S10—C14—N13 | 103.6 (2) | H48—C19—H49 | 110 (2) |
S10—C14—C15 | 119.5 (2) | H49—C19—H50 | 109.2 (19) |
N23—C15—C16 | 115.5 (3) | H48—C19—H50 | 109 (2) |
C14—C15—C16 | 85.1 (3) | C28—C26—H37 | 106.8 (5) |
N23—C15—C14 | 116.5 (3) | C24—C26—H37 | 109.0 (5) |
O17—C16—C15 | 135.4 (3) | N27—C26—H37 | 107.9 (5) |
O17—C16—N13 | 131.0 (4) | C28—C29—H41 | 120.0 (12) |
N13—C16—C15 | 93.0 (3) | C30—C29—H41 | 120.0 (11) |
O21—C20—C12 | 118.0 (4) | C29—C30—H42 | 119.4 (11) |
O21—C20—O22 | 126.3 (4) | C31—C30—H42 | 119.6 (11) |
O22—C20—C12 | 115.6 (4) | C32—C31—H52 | 120.0 (9) |
O25—C24—N23 | 124.5 (5) | C30—C31—H52 | 120.3 (9) |
O25—C24—C26 | 122.1 (5) | C31—C32—H43 | 120.1 (11) |
N23—C24—C26 | 113.2 (3) | C33—C32—H43 | 120.1 (11) |
C24—C26—C28 | 110.1 (3) | C28—C33—H44 | 119.9 (12) |
N27—C26—C24 | 110.0 (3) | C32—C33—H44 | 119.9 (12) |
N27—C26—C28 | 112.9 (3) | ||
C14—S10—C11—C12 | −39.8 (2) | C11—C12—C20—O21 | −124.3 (5) |
C14—S10—C11—C18 | 80.5 (3) | C11—C12—C20—O22 | 59.0 (6) |
C14—S10—C11—C19 | −160.1 (3) | N13—C12—C20—O21 | −3.6 (6) |
C11—S10—C14—N13 | 37.1 (2) | S10—C14—C15—C16 | −95.1 (3) |
C11—S10—C14—C15 | 131.6 (3) | S10—C14—C15—N23 | 21.1 (4) |
C14—N13—C16—C15 | 10.2 (3) | N13—C14—C15—C16 | 9.0 (3) |
C16—N13—C14—C15 | −10.0 (3) | N13—C14—C15—N23 | 125.1 (3) |
C14—N13—C12—C11 | −2.6 (4) | N23—C15—C16—O17 | 44.6 (8) |
C12—N13—C14—C15 | −146.1 (3) | C14—C15—C16—O17 | 161.7 (7) |
C14—N13—C12—C20 | −128.1 (4) | C14—C15—C16—N13 | −9.8 (3) |
C16—N13—C12—C20 | 113.4 (5) | N23—C15—C16—N13 | −126.9 (3) |
C16—N13—C12—C11 | −121.1 (4) | N23—C24—C26—C28 | 89.1 (5) |
C12—N13—C14—S10 | −26.5 (3) | O25—C24—C26—N27 | 37.9 (7) |
C16—N13—C14—S10 | 109.7 (3) | O25—C24—C26—C28 | −87.2 (6) |
C12—N13—C16—O17 | −33.5 (8) | N23—C24—C26—N27 | −145.8 (4) |
C12—N13—C16—C15 | 138.6 (4) | N27—C26—C28—C29 | 132.8 (5) |
C14—N13—C16—O17 | −161.9 (6) | N27—C26—C28—C33 | −54.6 (6) |
C15—N23—C24—O25 | 0.3 (9) | C24—C26—C28—C33 | 68.7 (6) |
C15—N23—C24—C26 | −175.9 (4) | C24—C26—C28—C29 | −103.8 (5) |
C24—N23—C15—C14 | 136.1 (5) | C26—C28—C33—C32 | −174.8 (5) |
C24—N23—C15—C16 | −126.3 (5) | C26—C28—C29—C30 | 172.0 (5) |
S10—C11—C12—C20 | 154.2 (3) | C33—C28—C29—C30 | −0.6 (8) |
S10—C11—C12—N13 | 29.6 (3) | C29—C28—C33—C32 | −2.2 (8) |
C19—C11—C12—N13 | 146.2 (3) | C28—C29—C30—C31 | 8.5 (8) |
C19—C11—C12—C20 | −89.2 (4) | C29—C30—C31—C32 | −13.5 (8) |
C18—C11—C12—C20 | 35.1 (4) | C30—C31—C32—C33 | 10.6 (9) |
C18—C11—C12—N13 | −89.5 (4) | C31—C32—C33—C28 | −2.8 (9) |
N13—C12—C20—O22 | 179.7 (4) |
Symmetry codes: (i) x, y, z−1; (ii) −x+1/2, −y+1, z−1/2; (iii) −x+1/2, −y+1, z+1/2; (iv) −x+3/2, −y+1, z−1/2; (v) −x+3/2, −y+1, z+1/2; (vi) x+1/2, −y+1/2, −z+1; (vii) −x+1, y−1/2, −z+1/2; (viii) −x+1, y−1/2, −z+3/2; (ix) x−1/2, −y+1/2, −z+1; (x) x, y, z+1; (xi) −x+1, y+1/2, −z+1/2; (xii) −x+1, y+1/2, −z+3/2; (xiii) x+1/2, −y+3/2, −z+1; (xiv) x−1/2, −y+3/2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H3···O4 | 0.98 | 2.02 | 2.9968 | 180 |
O4—H5···O7iv | 0.98 | 1.80 | 2.7850 | 180 |
O4—H6···O7 | 0.98 | 1.82 | 2.7967 | 180 |
O7—H8···O17 | 0.98 | 1.84 | 2.8225 | 180 |
O7—H9···O22vi | 0.98 | 1.74 | 2.7166 | 179 |
N27—H38···O4v | 1.001 (15) | 1.86 | 2.8272 | 161 |
N27—H39···O21xii | 1.00 (3) | 1.83 (3) | 2.742 (6) | 151.1 (15) |
N27—H40···O22xi | 1.00 (3) | 1.80 (2) | 2.688 (6) | 147 (2) |
N23—H51···O1 | 1.002 (10) | 1.97 | 2.9161 | 156 |
C14—H35···S10iii | 0.999 (6) | 2.869 (6) | 3.815 (4) | 158.3 (6) |
C26—H37···O1 | 1.080 (7) | 2.58 | 3.5092 | 143 |
C32—H43···O17xii | 1.079 (19) | 2.384 (16) | 3.228 (7) | 134.0 (16) |
Symmetry codes: (iii) −x+1/2, −y+1, z+1/2; (iv) −x+3/2, −y+1, z−1/2; (v) −x+3/2, −y+1, z+1/2; (vi) x+1/2, −y+1/2, −z+1; (xi) −x+1, y+1/2, −z+1/2; (xii) −x+1, y+1/2, −z+3/2. |
Acknowledgements
JB thanks Jesus College, Cambridge, for the award of a Junior Research Fellowship. Use of the National Synchrotron Light Source, Brookhaven National Laboratory, was supported by the US Department of Energy, Office of Science, Office of Basic Energy Sciences, under Contract No. De-AC02-98CH10886.
References
Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Boles, M. O. & Girven, R. J. (1976). Acta Cryst. B32, 2279–2284. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Boles, M. O., Girven, R. J. & Gane, P. A. C. (1978). Acta Cryst. B34, 461–466. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Boultif, A. & Louer, D. (1991). J. Appl. Cryst. 24, 987–993. CrossRef CAS Web of Science IUCr Journals Google Scholar
David, W. I. F., Shankland, K., Van de Streek, J., Pidcock, E. & Motherwell, S. (2004). DASH. Version 3.0. Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, England.. Google Scholar
David, W. I. F. & Sivia, D. S. (2001). J. Appl. Cryst. 34, 318–324. Web of Science CrossRef CAS IUCr Journals Google Scholar
Finger, L. W., Cox, D. E. & Jephcoat, A. P. (1994). J. Appl. Cryst. 27, 892–900. CrossRef CAS Web of Science IUCr Journals Google Scholar
James, M. N. G., Hall, D. & Hodgkin, D. C. (1968). Nature, 220, 168–170. CSD CrossRef CAS PubMed Web of Science Google Scholar
Larson, A. C. & Von Dreele, R. B. (2000). GSAS. Report LAUR 86-748. Los Alamos National Laboratory, New Mexico, USA. Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Thompson, P., Cox, D. E. & Hastings, J. B. (1987). J. Appl. Cryst. 20,79–83. CrossRef CAS Web of Science IUCr Journals Google Scholar
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