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A new restraint scheme for Rietveld refinement based on Morse bond energy potential is introduced, in which the asymmetry of the Morse potential allows the refinement to `break' the incorrectly placed bonds. The analysis of bond-length distributions at different values of restraint strength reveals a visible difference in behavior of wrong and correct structures, which can be detected using robust statistical methods. This fact is employed as a basis for a novel structure verification criterion. The approach is demonstrated on known difficult cases of acetolone and γ-quinacridone and used for the Rietveld refinement of N-(6-phenylhexanoyl)glycyl-L-tryptophanamide, an organic molecule of a potential anxiolytic containing 32 non-H atoms and 14 single bonds. The results are verified using density functional theory calculations with periodic boundary conditions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0021889812044147/db5105sup1.cif
Contains datablocks global, gb115amdata

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S0021889812044147/db5105sup2.rtv
Contains datablock gb115amdata

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0021889812044147/db5105sup3.pdf
Supplementary figures and tables

CCDC reference: 914668

Computing details top

Data collection: Bruker XRD Commander 2.6 (Bruker, 2007); cell refinement: TOPAS 4.2 (Coelho, 2003; Bruker, 2009); data reduction: TOPAS 4.2 (Coelho, 2003; Bruker, 2009); program(s) used to solve structure: FOX 1.9.7.0 (Favre-Nicolin, Cerny, 2002); program(s) used to refine structure: TOPAS 4.2 (Coelho, 2003; Bruker, 2009); molecular graphics: OLEX2 1.2 (Dolomanov, 2009); software used to prepare material for publication: PLATON (Spek, 2003).

(gb115amdata) top
Crystal data top
C25H30N4O3F(000) = 928
Mr = 434.53Dx = 1.244 Mg m3
Orthorhombic, P212121Cu Kα1 radiation, λ = 1.54056 Å
Hall symbol: P 2ac 2abµ = 0.67 mm1
a = 35.9422 (5) ÅT = 298 K
b = 12.91819 (12) ÅParticle morphology: round
c = 4.99532 (3) Åwhite
V = 2319.37 (4) Å3flat_sheet, 15 × 15 mm
Z = 4
Data collection top
Bruker D8 Advance Vario
diffractometer
Data collection mode: transmission
Radiation source: sealed X-ray tubeScan method: continuous
Ge 111 monochromator2θmin = 6.503°, 2θmax = 99.995°, 2θstep = 0.011°
Specimen mounting: deposied on sticky tape
Refinement top
Refinement on InetProfile function: pseudo-Voigt
Least-squares matrix: full with fixed elements per cycle197 parameters
Rp = 0.024139 restraints
Rwp = 0.035H-atom parameters constrained
Rexp = 0.009 1/Yi
RBragg = 0.013Background function: 12th order Chebyshev polynomial
8923 data pointsPreferred orientation correction: hkl dependent symmetrized spherical harmonics series (Jarvinen, 1993).
The coefficients used were:
y00 1
y20 0.662(8)
y22p -0.742(6)
y40 0.415(9)
y42p -0.028(5)
y44p 0.248(4)
Special details top

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 esds are taken into account in the estimation of

distances, angles and torsion angles

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O140.3867 (2)0.3686 (4)0.3911 (12)0.0380 (19)*
O180.4342 (2)0.1536 (4)0.3080 (13)0.0380 (19)*
O230.51609 (18)0.0385 (4)0.2462 (12)0.0380 (19)*
N130.3984 (2)0.2831 (5)0.0025 (8)0.028 (2)*
N170.45853 (19)0.0624 (4)0.0217 (9)0.028 (2)*
N220.5433 (2)0.0847 (5)0.1381 (12)0.028 (2)*
N270.44546 (19)0.3208 (4)0.1978 (12)0.028 (2)*
C10.23521 (12)0.7751 (4)0.1091 (11)0.0627 (16)*
C20.24949 (12)0.8457 (5)0.2883 (14)0.0627 (16)*
C30.19754 (13)0.7817 (5)0.0384 (13)0.0627 (16)*
C40.22679 (13)0.9206 (4)0.3960 (13)0.0627 (16)*
C50.17444 (16)0.8516 (5)0.1617 (13)0.0627 (16)*
C60.18769 (12)0.9131 (5)0.3560 (13)0.0627 (16)*
C70.26074 (18)0.7049 (5)0.0405 (12)0.0627 (16)*
C80.2816 (2)0.6299 (5)0.1400 (9)0.0627 (16)*
C90.31144 (19)0.5718 (5)0.0140 (11)0.0627 (16)*
C100.3324 (2)0.4943 (5)0.1531 (11)0.0627 (16)*
C110.3594 (2)0.4368 (4)0.0057 (10)0.0627 (16)*
C120.37949 (19)0.3572 (4)0.1489 (8)0.0627 (16)*
C150.4211 (3)0.2054 (5)0.1339 (11)0.0627 (16)*
C160.43996 (18)0.1412 (4)0.0687 (7)0.0627 (16)*
C190.48213 (14)0.0020 (4)0.1440 (10)0.0627 (16)*
C200.45903 (19)0.0961 (5)0.2532 (10)0.0627 (16)*
C210.51738 (12)0.0333 (4)0.0081 (8)0.0627 (16)*
C240.44612 (14)0.1749 (4)0.0442 (11)0.0627 (16)*
C250.46544 (17)0.2604 (5)0.0219 (15)0.0627 (16)*
C260.41363 (14)0.1760 (3)0.1220 (10)0.0627 (16)*
C280.41603 (13)0.2668 (3)0.2831 (11)0.0627 (16)*
C290.3857 (2)0.1023 (4)0.1869 (13)0.0627 (16)*
C300.3901 (2)0.2896 (4)0.4766 (12)0.0627 (16)*
C310.35753 (18)0.1306 (4)0.3582 (13)0.0627 (16)*
C320.36097 (19)0.2138 (5)0.5193 (13)0.0627 (16)*
H20.274740.846840.328760.075 (2)*
H30.187000.732110.073170.075 (2)*
H40.235930.965370.526070.075 (2)*
H50.149060.848810.126270.075 (2)*
H60.172480.965270.422920.075 (2)*
H7A0.245830.664820.164690.075 (2)*
H7B0.278100.747660.139830.075 (2)*
H8A0.293600.668310.282830.075 (2)*
H8B0.263480.582680.216050.075 (2)*
H9A0.299910.536080.163320.075 (2)*
H9B0.329330.621630.081430.075 (2)*
H10A0.345040.532590.293150.075 (2)*
H10B0.316190.442910.233320.075 (2)*
H11A0.345980.406070.154260.075 (2)*
H11B0.377750.485130.074030.075 (2)*
H130.392410.272620.167080.075 (2)*
H15A0.404900.162980.244220.075 (2)*
H15B0.439900.237430.245540.075 (2)*
H170.457300.049360.190310.075 (2)*
H190.489580.041070.296280.075 (2)*
H20A0.436700.069670.338240.075 (2)*
H20B0.474450.130060.386100.075 (2)*
H22A0.555630.133630.062040.075 (2)*
H22B0.542710.080550.309880.075 (2)*
H250.482140.290380.097340.075 (2)*
H270.454580.372200.285220.075 (2)*
H290.380660.051220.060870.075 (2)*
H300.395470.342160.597680.075 (2)*
H310.335820.091770.371240.075 (2)*
H320.346630.214610.674260.075 (2)*
Geometric parameters (Å, º) top
O14—C121.246 (7)C24—C261.433 (7)
O18—C161.224 (7)C26—C281.425 (6)
O23—C211.192 (7)C26—C291.421 (8)
N13—C121.397 (8)C28—C301.375 (8)
N13—C151.462 (10)C29—C311.375 (9)
N17—C161.298 (8)C30—C321.449 (9)
N17—C191.448 (8)C31—C321.348 (9)
N22—C211.357 (8)C2—H20.9300
N27—C251.377 (9)C3—H30.9300
N27—C281.337 (8)C4—H40.9300
N13—H130.8600C5—H50.9300
N17—H170.8600C6—H60.9300
N22—H22A0.8600C7—H7A0.9700
N22—H22B0.8600C7—H7B0.9700
N27—H270.8600C8—H8A0.9700
C1—C31.402 (7)C8—H8B0.9700
C1—C21.377 (8)C9—H9A0.9700
C1—C71.491 (8)C9—H9B0.9700
C2—C41.375 (8)C10—H10A0.9700
C3—C51.373 (9)C10—H10B0.9700
C4—C61.423 (6)C11—H11A0.9700
C5—C61.342 (9)C11—H11B0.9700
C7—C81.521 (9)C15—H15A0.9700
C8—C91.518 (9)C15—H15B0.9700
C9—C101.506 (9)C19—H190.9800
C10—C111.457 (9)C20—H20A0.9700
C11—C121.475 (8)C20—H20B0.9700
C15—C161.474 (9)C25—H250.9300
C19—C201.570 (8)C29—H290.9300
C19—C211.532 (7)C30—H300.9300
C20—C241.530 (8)C31—H310.9300
C24—C251.346 (8)C32—H320.9300
C12—N13—C15119.3 (4)C5—C3—H3118.00
C16—N17—C19123.6 (4)C2—C4—H4120.00
C25—N27—C28108.7 (5)C6—C4—H4119.00
C12—N13—H13120.00C3—C5—H5119.00
C15—N13—H13118.00C6—C5—H5121.00
C16—N17—H17118.00C4—C6—H6119.00
C19—N17—H17119.00C5—C6—H6119.00
H22A—N22—H22B120.00C1—C7—H7A108.00
C21—N22—H22B119.00C1—C7—H7B108.00
C21—N22—H22A118.00C8—C7—H7A108.00
C25—N27—H27124.00C8—C7—H7B110.00
C28—N27—H27123.00H7A—C7—H7B109.00
C2—C1—C3118.9 (5)C7—C8—H8A109.00
C2—C1—C7120.0 (4)C7—C8—H8B108.00
C3—C1—C7120.3 (5)C9—C8—H8A108.00
C1—C2—C4119.9 (4)C9—C8—H8B111.00
C1—C3—C5120.7 (6)H8A—C8—H8B109.00
C2—C4—C6118.9 (5)C8—C9—H9A109.00
C3—C5—C6120.0 (5)C8—C9—H9B108.00
C4—C6—C5119.5 (5)C10—C9—H9A109.00
C1—C7—C8113.2 (5)C10—C9—H9B108.00
C7—C8—C9111.3 (4)H9A—C9—H9B109.00
C8—C9—C10113.7 (5)C9—C10—H10A107.00
C9—C10—C11111.7 (5)C9—C10—H10B113.00
C10—C11—C12113.4 (4)C11—C10—H10A110.00
O14—C12—N13120.4 (6)C11—C10—H10B106.00
O14—C12—C11121.9 (5)H10A—C10—H10B109.00
N13—C12—C11115.6 (4)C10—C11—H11A107.00
N13—C15—C16108.9 (4)C10—C11—H11B108.00
N17—C16—C15116.0 (4)C12—C11—H11A111.00
O18—C16—C15121.3 (6)C12—C11—H11B107.00
O18—C16—N17122.0 (5)H11A—C11—H11B109.00
N17—C19—C21110.7 (4)N13—C15—H15A108.00
C20—C19—C21113.9 (4)N13—C15—H15B111.00
N17—C19—C20109.5 (5)C16—C15—H15A110.00
C19—C20—C24116.0 (4)C16—C15—H15B108.00
O23—C21—C19118.5 (5)H15A—C15—H15B109.00
O23—C21—N22122.4 (5)N17—C19—H19106.00
N22—C21—C19115.5 (4)C20—C19—H19108.00
C20—C24—C26130.5 (5)C21—C19—H19108.00
C25—C24—C26105.7 (5)C19—C20—H20A108.00
C20—C24—C25123.8 (5)C19—C20—H20B107.00
N27—C25—C24110.6 (6)C24—C20—H20A106.00
C24—C26—C28106.6 (4)C24—C20—H20B110.00
C24—C26—C29134.5 (4)H20A—C20—H20B109.00
C28—C26—C29117.7 (5)N27—C25—H25121.00
C26—C28—C30122.2 (4)C24—C25—H25121.00
N27—C28—C30130.5 (5)C26—C29—H29117.00
N27—C28—C26107.3 (5)C31—C29—H29118.00
C26—C29—C31119.0 (5)C28—C30—H30118.00
C28—C30—C32116.7 (5)C32—C30—H30123.00
C29—C31—C32121.1 (6)C29—C31—H31121.00
C30—C32—C31121.1 (6)C32—C31—H31118.00
C1—C2—H2121.00C30—C32—H32121.00
C4—C2—H2119.00C31—C32—H32117.00
C1—C3—H3120.00
C12—N13—C15—C16176.3 (6)N13—C15—C16—O183.4 (10)
C15—N13—C12—O1412.2 (10)N17—C19—C21—O2327.5 (7)
C15—N13—C12—C11175.9 (7)C21—C19—C20—C2457.5 (6)
C19—N17—C16—C15172.8 (6)C20—C19—C21—N2262.8 (6)
C16—N17—C19—C2092.2 (7)N17—C19—C21—N22173.3 (5)
C19—N17—C16—O1816.8 (10)C20—C19—C21—O2396.4 (6)
C16—N17—C19—C21141.5 (6)N17—C19—C20—C2467.0 (6)
C25—N27—C28—C2610.1 (7)C19—C20—C24—C2592.6 (7)
C25—N27—C28—C30173.2 (6)C19—C20—C24—C2686.0 (7)
C28—N27—C25—C2410.7 (8)C20—C24—C26—C28178.9 (5)
C3—C1—C7—C8125.9 (6)C26—C24—C25—N276.3 (7)
C7—C1—C3—C5175.2 (6)C25—C24—C26—C29167.1 (6)
C3—C1—C2—C40.5 (9)C20—C24—C26—C2911.7 (10)
C2—C1—C7—C864.4 (7)C25—C24—C26—C280.1 (6)
C7—C1—C2—C4170.3 (6)C20—C24—C25—N27174.8 (5)
C2—C1—C3—C55.4 (9)C24—C26—C28—C30176.7 (5)
C1—C2—C4—C610.6 (9)C29—C26—C28—N27175.9 (5)
C1—C3—C5—C61.4 (10)C24—C26—C29—C31179.8 (6)
C2—C4—C6—C517.4 (9)C28—C26—C29—C3114.2 (8)
C3—C5—C6—C412.7 (10)C29—C26—C28—C307.1 (8)
C1—C7—C8—C9171.2 (5)C24—C26—C28—N276.3 (6)
C7—C8—C9—C10178.5 (5)N27—C28—C30—C32179.4 (6)
C8—C9—C10—C11177.1 (5)C26—C28—C30—C323.1 (8)
C9—C10—C11—C12177.8 (5)C26—C29—C31—C3218.2 (9)
C10—C11—C12—O1432.2 (9)C28—C30—C32—C316.5 (9)
C10—C11—C12—N13164.3 (6)C29—C31—C32—C3014.4 (10)
N13—C15—C16—N17173.9 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N13—H13···O14i0.86002.54003.252 (7)141.00
N13—H13···O180.86002.26002.605 (9)104.00
N22—H22A···O14ii0.86002.24002.866 (10)129.00
N22—H22B···O23i0.86002.48003.282 (9)156.00
N27—H27···O23ii0.86002.40003.146 (8)146.00
C15—H15A···O18iii0.97002.48002.906 (9)107.00
C15—H15B···O18iii0.97002.49002.906 (9)106.00
Symmetry codes: (i) x, y, z1; (ii) x+1, y1/2, z+1/2; (iii) x, y, z+1.
 

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