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The crystal structures of five hemiadducts of paracetamol with 1,4-dioxane, N-methylmorpholine, morpholine, N,N-dimethylpiperazine and piperazine and a related 1:1 adduct of paracetamol with 4,4′-bipyridine are described. All structures are characterized by the formation of chains of paracetamol molecules, which are linked via either OH...O=C interactions [C(9) chains in graph-set notation] or NH...O=C interactions [C(4) chains], depending on the presence or absence of substituent groups on the guest molecule. In all cases except for the morpholine and bipyridine adducts these chains are connected by hydrogen-bond interactions with the guest molecules, which reside on crystallographic inversion centres. In the bipyridine adduct this linkage also involves a π-stacking interaction; in the morpholine adduct it is formed between the OH groups of two opposed paracetamol molecules. Most adducts (that with 4,4′-bipyridine is an exception) decompose on heating to give monoclinic paracetamol. This is the first systematic study of a series of co-crystals containing paracetamol.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768102015987/an0622sup1.cif
Contains datablocks parody, pardmp, parnmm, ppip02, pardip, pmor02, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102015987/an0622parodysup2.hkl
Contains datablock parody

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102015987/an0622pardmpsup3.hkl
Contains datablock pardmp

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102015987/an0622parnmmsup4.hkl
Contains datablock parnmm

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102015987/an0622ppip02sup5.hkl
Contains datablock ppip02

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102015987/an0622pardipsup6.hkl
Contains datablock pardip

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102015987/an0622pmor02sup7.hkl
Contains datablock pmor02

CCDC references: 201631; 201632; 201633; 201634; 201635; 201636

Computing details top

Data collection: Stoe DIF4 for parody; Bruker SMART for pardmp, pmor02; Smart for ppip02; SMART for pardip. Cell refinement: Stoe DIF4 for parody; Bruker SMART for pardmp, parnmm, pmor02; Saint for ppip02; SAINT for pardip. Data reduction: Stoe REDU4 for parody; Bruker SAINT for pardmp; Bruker SHELXTL for parnmm, pmor02; Saint for ppip02; SAINT for pardip. For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: SHELXTL for parody, ppip02, pardip; Bruker SHELXTL for pardmp, parnmm, pmor02. Software used to prepare material for publication: Bruker SHELXTL for pardmp, pmor02; SHELXTL for parnmm, ppip02, pardip.

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
(parody) top
Crystal data top
2[C8H9O2N]·[C4H8O2]F(000) = 832
Mr = 390.43Dx = 1.293 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
a = 12.421 (5) ÅCell parameters from 80 reflections
b = 12.056 (4) Åθ = 20–22°
c = 13.396 (3) ŵ = 0.80 mm1
β = 91.51 (3)°T = 220 K
V = 2005.4 (11) Å3Lath, colourless
Z = 40.78 × 0.19 × 0.16 mm
Data collection top
Radiation source: fine-focus sealed tubeRint = 0.053
Graphite monochromatorθmax = 69.8°, θmin = 3.6°
ωθ scansh = 1515
Absorption correction: empirical
Psi-scans
k = 014
Tmin = 0.602, Tmax = 0.826l = 015
4865 measured reflections3 standard reflections every 60 min
3499 independent reflections intensity decay: 10.9%
2508 reflections with I > 2σ(I)
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)] = 0.070H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.224 w = 1/[σ2(Fo2) + (0.125P)2 + 1.1494P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.002
3499 reflectionsΔρmax = 0.50 e Å3
285 parametersΔρmin = 0.26 e Å3
60 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0019 (6)
Crystal data top
2[C8H9O2N]·[C4H8O2]V = 2005.4 (11) Å3
Mr = 390.43Z = 4
Monoclinic, P21/cCu Kα radiation
a = 12.421 (5) ŵ = 0.80 mm1
b = 12.056 (4) ÅT = 220 K
c = 13.396 (3) Å0.78 × 0.19 × 0.16 mm
β = 91.51 (3)°
Data collection top
Absorption correction: empirical
Psi-scans
2508 reflections with I > 2σ(I)
Tmin = 0.602, Tmax = 0.826Rint = 0.053
4865 measured reflections3 standard reflections every 60 min
3499 independent reflections intensity decay: 10.9%
Refinement top
R[F2 > 2σ(F2)] = 0.07060 restraints
wR(F2) = 0.224H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.50 e Å3
3499 reflectionsΔρmin = 0.26 e Å3
285 parameters
Special details top

Experimental. INTENSITY STATISTICS FOR DATASET # 1 PARODY.hkl

Resolution #Data #Theory %Complete Redundancy Mean I Mean I/s R(int) R(sigma)

Inf - 2.35 189 189 100.0 1.00 218.6 74.30 0.0068 2.35 - 1.80 210 212 99.1 0.99 77.1 41.71 0.0149 1.80 - 1.55 219 220 99.5 1.11 47.7 29.41 0.0263 0.0221 1.55 - 1.40 217 217 100.0 1.24 21.5 18.32 0.0349 0.0424 1.40 - 1.30 202 202 100.0 1.29 13.8 12.05 0.0442 0.0620 1.30 - 1.20 270 270 100.0 1.36 20.7 14.91 0.0423 0.0483 1.20 - 1.10 381 382 99.7 1.37 17.6 13.79 0.0329 0.0565 1.10 - 1.05 248 248 100.0 1.48 11.4 10.14 0.0566 0.0798 1.05 - 1.00 293 293 100.0 1.48 7.7 7.26 0.1082 0.1081 1.00 - 0.95 349 355 98.3 1.51 6.5 7.20 0.0830 0.1182 0.95 - 0.90 444 460 96.5 1.52 4.4 5.68 0.1029 0.1516 0.90 - 0.85 407 563 72.3 1.13 2.8 4.44 0.1332 0.1983 0.85 - 0.82 256 374 68.4 1.09 1.9 3.97 0.1446 0.2387 —————————————————————————— 0.95 - 0.82 1107 1397 79.2 1.24 3.2 4.83 0.1189 0.1784 Inf - 0.82 3685 3985 92.5 1.29 26.8 15.58 0.0570 0.0320

Merged [A], lowest resolution = 13.39 Angstroms, 18 outliers downweighted

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. TITL parody in P2(1)/c CELL 1.54184 12.4214 12.0560 13.3962 90.0000 91.5100 90.0000 ZERR 4.00 0.0047 0.0039 0.0034 0.0000 0.0280 0.0000 L A T T 1 SYMM –X, 0.5+Y, 0.5-Z SFAC C H N O UNIT 80 104 8 24 TEMP -53 REM ROTAX=> TWINED ABOUT 1. 0. 0. reciprocal lattice direction BUT SCALE REM REFINED TO ONLY 2.6 (3)%, R1 DROPPED TO 6.86%. THIS WAS LEFT OUT THOUGH. L·S. 6 ACTA HTAB EQIV $1 X, Y, Z+1 RTAB D1 H1A O1S RTAB D2 H11A O2B RTAB D3 H11B O2A_$1 RTAB D4 H1B O1U RTAB D5 H1B O1T BOND $H MPLA 6 C1A C2A C3A C4A C5A C6A MPLA 4 C1A C7A O2A C8A MPLA 6 C1B C2B C3B C4B C5B C6B MPLA 4 C1B C7B O2B C8B

OMIT 1 7 3 OMIT -2 4 1 DELU O1T > C2U

SIMU O1T > C2U FMAP 2 PLAN -10 W GH T 0.125000 1.149400 EXTI 0.001924 FVAR 0.20621 N1A 3 0.647553 0.188806 0.546664 11.00000 0.05317 0.03172 = 0.04914 0.00371 - 0.00585 0.00550 AFIX 43 H1A 2 0.627333 0.254093 0.525820 11.00000 - 1.20000 AFIX 0 O1A 4 0.870843 0.162003 0.911226 11.00000 0.08574 0.05345 = 0.04486 0.00215 - 0.01670 - 0.01152 AFIX 147 H11A 2 0.851394 0.106876 0.943192 11.00000 - 1.50000 AFIX 0 C1A 1 0.812279 0.168527 0.823718 11.00000 0.05628 0.03950 = 0.03948 - 0.00416 0.00110 - 0.00194 O2A 4 0.650894 0.006213 0.509556 11.00000 0.07917 0.03729 = 0.04321 - 0.00309 - 0.00033 0.00717 C2A 1 0.834402 0.253942 0.757973 11.00000 0.05853 0.04090 = 0.05113 - 0.00059 - 0.00264 - 0.01190 AFIX 43 H2A 2 0.886990 0.307237 0.774981 11.00000 - 1.20000 AFIX 0 C3A 1 0.778935 0.260434 0.667472 11.00000 0.05527 0.03300 = 0.04554 0.00321 0.00351 - 0.00161 AFIX 43 H3A 2 0.794501 0.318118 0.622902 11.00000 - 1.20000 AFIX 0 C4A 1 0.700475 0.182883 0.641434 11.00000 0.04561 0.03096 = 0.04154 0.00163 0.00016 0.00355 C5A 1 0.675563 0.100138 0.710393 11.00000 0.05160 0.03475 = 0.04740 - 0.00074 0.00203 - 0.00550 AFIX 43 H5A 2 0.620343 0.049096 0.695124 11.00000 - 1.20000 AFIX 0 C6A 1 0.730911 0.092909 0.799859 11.00000 0.05912 0.03643 = 0.03987 0.00452 - 0.00013 - 0.00508 AFIX 43 H6A 2 0.713906 0.036640 0.845388 11.00000 - 1.20000 AFIX 0 C7A 1 0.625947 0.102694 0.486394 11.00000 0.04726 0.03859 = 0.04200 0.00164 0.00377 0.00000 C8A 1 0.569905 0.128773 0.388993 11.00000 0.06461 0.04740 = 0.05141 0.00358 - 0.00638 - 0.00093 AFIX 137 H8A1 2 0.574728 0.065427 0.344692 11.00000 - 1.50000 H8A2 2 0.603851 0.192482 0.358747 11.00000 - 1.50000 H8A3 2 0.494801 0.145319 0.400386 11.00000 - 1.50000 AFIX 0 O1B 4 0.622086 - 0.183587 1.407086 11.00000 0.07798 0.04700 = 0.05814 - 0.00405 0.01891 - 0.01017 AFIX 147 H11B 2 0.630821 - 0.123424 1.436310 11.00000 - 1.50000 AFIX 0 N1B 3 0.856138 - 0.199388 1.058485 11.00000 0.05541 0.03844 = 0.04698 - 0.00535 0.00820 0.00026 AFIX 43 H1B 2 0.883411 - 0.263187 1.042360 11.00000 - 1.20000 AFIX 0 C1B 1 0.682050 - 0.185318 1.323765 11.00000 0.05321 0.03788 = 0.04407 0.00175 0.00106 0.00029 O2B 4 0.834640 - 0.021338 1.012777 11.00000 0.07847 0.05524 = 0.05307 0.00694 0.00638 0.01199 C2B 1 0.674935 - 0.276248 1.261612 11.00000 0.05324 0.03863 = 0.05146 0.00088 - 0.00126 - 0.00761 AFIX 43 H2B 2 0.630543 - 0.336098 1.278677 11.00000 - 1.20000 AFIX 0 C3B 1 0.732059 - 0.280785 1.174595 11.00000 0.05261 0.03468 = 0.04962 - 0.00645 - 0.00062 - 0.00061 AFIX 43 H3B 2 0.725227 - 0.342698 1.132250 11.00000 - 1.20000 AFIX 0 C4B 1 0.799461 - 0.193953 1.149782 11.00000 0.04603 0.03916 = 0.03923 - 0.00100 - 0.00122 0.00230 C5B 1 0.810339 - 0.104631 1.213661 11.00000 0.05712 0.04241 = 0.04646 - 0.00361 0.00150 - 0.00856 AFIX 43 H5B 2 0.857571 - 0.046514 1.198340 11.00000 - 1.20000 AFIX 0 C6B 1 0.752159 - 0.100239 1.299980 11.00000 0.06361 0.03884 = 0.04410 - 0.00768 0.00358 - 0.00718 AFIX 43 H6B 2 0.760102 - 0.039058 1.343045 11.00000 - 1.20000 AFIX 0 C7B 1 0.870793 - 0.115308 0.996026 11.00000 0.04573 0.05277 = 0.04466 - 0.00522 - 0.00178 - 0.00093 C8B 1 0.931015 - 0.140142 0.904057 11.00000 0.06024 0.06879 = 0.05227 - 0.00392 0.00922 - 0.00990 AFIX 137 H8B1 2 0.889609 - 0.114935 0.845989 11.00000 - 1.50000 H8B2 2 0.942794 - 0.219478 0.899243 11.00000 - 1.50000 H8B3 2 0.999887 - 0.102198 0.907006 11.00000 - 1.50000 AFIX 0 O1S 4 0.564588 0.405519 0.491593 11.00000 0.06352 0.04298 = 0.07589 - 0.00944 - 0.01434 0.01239 C1S 1 0.461246 0.411368 0.444904 11.00000 0.07522 0.03947 = 0.08315 - 0.00754 - 0.02219 0.00060 AFIX 23 H1S1 2 0.407892 0.379869 0.489451 11.00000 - 1.20000 H1S2 2 0.460548 0.367138 0.383513 11.00000 - 1.20000 AFIX 0 C2S 1 0.568573 0.472343 0.579589 11.00000 0.05583 0.05096 = 0.05651 0.00515 - 0.00652 0.00353 AFIX 23 H2S1 2 0.641418 0.470390 0.609469 11.00000 - 1.20000 H2S2 2 0.518765 0.442556 0.628388 11.00000 - 1.20000 AFIX 0 PART 1 O1T 4 0.977923 - 0.409314 1.060845 10.75000 0.07751 0.03231 = 0.08008 - 0.01188 0.03073 - 0.00901 C1T 1 0.940056 - 0.519544 1.082738 10.75000 0.06607 0.03286 = 0.08222 - 0.00679 0.02511 - 0.01185 AFIX 23 H1T1 2 0.871705 - 0.514662 1.117380 10.75000 - 1.20000 H1T2 2 0.992427 - 0.556898 1.127205 10.75000 - 1.20000 AFIX 0 C2T 1 1.075517 - 0.414824 1.009266 10.75000 0.05141 0.03300 = 0.08747 - 0.00274 0.00843 - 0.00968 AFIX 23 H2T1 2 1.131350 - 0.449230 1.052038 10.75000 - 1.20000 H2T2 2 1.099319 - 0.339777 0.992432 10.75000 - 1.20000 AFIX 0 PART 2 O1U 4 0.937035 - 0.405319 1.003640 10.25000 0.07123 0.03622 = 0.08101 0.00228 0.01787 0.01315 C1U 1 0.942018 - 0.482326 1.086717 10.25000 0.06223 0.03256 = 0.04542 - 0.01813 0.01260 0.00818 AFIX 23 H1U1 2 0.873840 - 0.481683 1.121898 10.25000 - 1.20000 H1U2 2 0.999957 - 0.461063 1.133973 10.25000 - 1.20000 AFIX 0 C2U 1 1.037378 - 0.406048 0.953735 10.25000 0.08773 0.04403 = 0.09297 - 0.00707 0.03994 - 0.00869 AFIX 23 H2U1 2 1.095722 - 0.385213 1.000718 10.25000 - 1.20000 H2U2 2 1.035235 - 0.351767 0.899264 10.25000 - 1.20000 PART 0

HKLF 4

REM parody in P2(1)/c REM R1 = 0.0702 for 2508 Fo > 4sig(Fo) and 0.0942 for all 3499 data REM 285 parameters refined using 60 restraints

END

WGHT 0.1270 1.1079 REM Highest difference peak 0.503, deepest hole -0.260, 1-σ level 0.070 Q1 1 0.5269 0.4008 0.5514 11.00000 0.05 0.50 Q2 1 0.7676 - 0.1898 1.0558 11.00000 0.05 0.29 Q3 1 0.9245 0.0043 0.9999 11.00000 0.05 0.28 Q4 1 0.6851 - 0.3043 1.1039 11.00000 0.05 0.28 Q5 1 0.7656 0.2679 0.7732 11.00000 0.05 0.27 Q6 1 0.7565 - 0.2954 1.2765 11.00000 0.05 0.27 Q7 1 0.6894 0.0176 0.5990 11.00000 0.05 0.26 Q8 1 0.5952 0.4102 0.6485 11.00000 0.05 0.26 Q9 1 0.5910 - 0.1801 1.3127 11.00000 0.05 0.24 Q10 1 0.6636 - 0.2082 1.5081 11.00000 0.05 0.24

#=============================================================================== # PLATON/CHECK-(191101) versus check.def version of 16/11/01 for entry: parody # Data From: parody.cif - Data Type: CIF Bond Precision C—C = 0.0054 A # # CELL 1.54184 12.421 12.056 13.396 90.00 91.51 90.00 2005.30 # SpaceGroup from Symmetry P21/c Hall: –P 2ybc # Reported P21/c ? # MoietyFormula C4 H8 O2, 2(C8 H9 N O2) # Reported 2[C8H9O2N]·[C4H8O2] # SumFormula C20 H26 N2 O6 # Reported C20 H26 N2 O6 # Mr = 390.43[Calc], 390.43[Rep] # Dx,gcm-3 = 1.293[Calc], 1.293[Rep] # Z = 4[Calc], 4[Rep] # Mu (mm-1) = 0.795[Calc], 0.795[Rep] # F000 = 832.0[Calc], 832.0[Rep] # Reported T limits: Tmin=0.602 Tmax=0.826 'EMPIRICAL' # Calculated T limits: Tmin=0.834 Tmin'=0.538 Tmax=0.881 # Reported Hmax= 15, Kmax= 14, Lmax= 15, Nref= 3499, Th(max)= 69.79 # Calculated Hmax= 15, Kmax= 14, Lmax= 16, Nref= 3783 (3783), Ratio= 0.92 (0.92) # R= 0.0702 (2508), wR2= 0.2243 (3499), S = 1.078, Npar= 285 #=============================================================================== >>> The Following ALERTS were generated <<<

028_ALERT A -diffrn-measured-fraction-theta-max low ···.. 0.92

The data were collected on a four-circle with Cu—Kα radiation. Some high angle data were inaccessible, see able above for coverage statistics.

#=============================================================================== 413_ALERT B Short Inter XH3.. XHn: H(82B).. <H(22U) = 1.96 A ng.

H22U has an occupancy of 0.25. It is possible that the methyl group based on C8B is also disordered, although this was not evident in a difference map and it has not been modelled.

#=============================================================================== 022_ALERT C Ratio Unique / Expected Reflections too Low.. 0.93 029_ALERT C -diffrn-measured-fraction-theta-full low ···.. 0.92

The data were collected on a four-circle with Cu—Kα radiation. Some high angle data were inaccessible, see able above for coverage statistics.

030_ALERT C Refined Extinction parameter within range ···. 3.17 Sigma

This is more than σ, so I think it should stay in.

042_ALERT C Calc. and Rep. MoietyFormula Strings Differ.. ?

Just a different atom order.

062_ALERT C Rescale T(min) & T(max) by ··················. 1.07 063_ALERT C Crystal Probably too Large for Beam Size ···.. 0.78 mm

A 0.8 mm collimator was used.

125_ALERT C No _symmetry_space_group_name_Hall given ···.. ?

-P 2ybc

302_ALERT C Anion/Solvent Disorder ·····················.. 33.00 Perc.

See text.

340_ALERT C Low Bond Precision on C—C bonds (x 1000) Ang.. 5

A possible function of the disorder/twinning in the structure.

790_ALERT C Centre of Gravity not Within Unit Cell: Resd.# 1 C4 H8 O2 790_ALERT C Centre of Gravity not Within Unit Cell: Resd.# 3 C8 H9 N O2

Asymetric unit was chosen to given a logical H-bonded fragment.

ALERT Level Summary 1 ALERT Level A = In General: Serious Problem 1 ALERT Level B = Potentially Serious Problem 11 ALERT Level C = Check & Explain

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N1A0.6476 (2)0.1888 (2)0.5467 (2)0.0448 (7)
H1A0.62730.25410.52580.054*
O1A0.8708 (2)0.1620 (2)0.9112 (2)0.0617 (8)
H11A0.85140.10690.94320.093*
C1A0.8123 (3)0.1685 (3)0.8237 (3)0.0451 (8)
O2A0.6509 (2)0.00621 (19)0.50956 (18)0.0533 (7)
C2A0.8344 (3)0.2539 (3)0.7580 (3)0.0503 (9)
H2A0.88700.30720.77500.060*
C3A0.7789 (3)0.2604 (3)0.6675 (3)0.0446 (8)
H3A0.79450.31810.62290.053*
C4A0.7005 (2)0.1829 (3)0.6414 (2)0.0394 (7)
C5A0.6756 (3)0.1001 (3)0.7104 (3)0.0446 (8)
H5A0.62030.04910.69510.053*
C6A0.7309 (3)0.0929 (3)0.7999 (3)0.0452 (8)
H6A0.71390.03660.84540.054*
C7A0.6259 (3)0.1027 (3)0.4864 (3)0.0426 (8)
C8A0.5699 (3)0.1288 (3)0.3890 (3)0.0546 (9)
H8A10.57470.06540.34470.082*
H8A20.60390.19250.35870.082*
H8A30.49480.14530.40040.082*
O1B0.6221 (2)0.1836 (2)1.4071 (2)0.0607 (7)
H11B0.63080.12341.43630.091*
N1B0.8561 (2)0.1994 (2)1.0585 (2)0.0468 (7)
H1B0.88340.26321.04240.056*
C1B0.6821 (3)0.1853 (3)1.3238 (3)0.0451 (8)
O2B0.8346 (2)0.0213 (2)1.0128 (2)0.0622 (7)
C2B0.6749 (3)0.2762 (3)1.2616 (3)0.0478 (8)
H2B0.63050.33611.27870.057*
C3B0.7321 (3)0.2808 (3)1.1746 (3)0.0457 (8)
H3B0.72520.34271.13220.055*
C4B0.7995 (3)0.1940 (3)1.1498 (2)0.0415 (7)
C5B0.8103 (3)0.1046 (3)1.2137 (3)0.0487 (8)
H5B0.85760.04651.19830.058*
C6B0.7522 (3)0.1002 (3)1.3000 (3)0.0488 (8)
H6B0.76010.03911.34300.059*
C7B0.8708 (3)0.1153 (3)0.9960 (3)0.0478 (8)
C8B0.9310 (3)0.1401 (4)0.9041 (3)0.0603 (10)
H8B10.88960.11490.84600.090*
H8B20.94280.21950.89920.090*
H8B30.99990.10220.90700.090*
O1S0.5646 (2)0.4055 (2)0.4916 (2)0.0611 (7)
C1S0.4612 (4)0.4114 (3)0.4449 (4)0.0664 (12)
H1S10.40790.37990.48950.080*
H1S20.46050.36710.38350.080*
C2S0.5686 (3)0.4723 (3)0.5796 (3)0.0546 (9)
H2S10.64140.47040.60950.065*
H2S20.51880.44260.62840.065*
O1T0.9779 (4)0.4093 (4)1.0608 (4)0.0628 (12)0.75
C1T0.9401 (10)0.5195 (6)1.0827 (9)0.060 (3)0.75
H1T10.87170.51471.11740.072*0.75
H1T20.99240.55691.12720.072*0.75
C2T1.0755 (5)0.4148 (5)1.0093 (6)0.0572 (15)0.75
H2T11.13140.44921.05200.069*0.75
H2T21.09930.33980.99240.069*0.75
O1U0.9370 (11)0.4053 (10)1.0036 (12)0.063 (3)0.25
C1U0.942 (3)0.482 (2)1.087 (2)0.047 (5)0.25
H1U10.87380.48171.12190.056*0.25
H1U21.00000.46111.13400.056*0.25
C2U1.037 (2)0.4060 (18)0.954 (2)0.074 (5)0.25
H2U11.09570.38521.00070.089*0.25
H2U21.03520.35180.89930.089*0.25
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0532 (15)0.0317 (14)0.0491 (18)0.0055 (11)0.0059 (13)0.0037 (12)
O1A0.0857 (19)0.0534 (16)0.0449 (16)0.0115 (13)0.0167 (13)0.0022 (12)
C1A0.0563 (19)0.0395 (17)0.0395 (19)0.0019 (14)0.0011 (14)0.0042 (14)
O2A0.0792 (17)0.0373 (13)0.0432 (14)0.0072 (11)0.0003 (12)0.0031 (10)
C2A0.059 (2)0.0409 (18)0.051 (2)0.0119 (15)0.0026 (16)0.0006 (15)
C3A0.0553 (18)0.0330 (16)0.046 (2)0.0016 (14)0.0035 (15)0.0032 (14)
C4A0.0456 (16)0.0310 (15)0.0415 (19)0.0035 (12)0.0002 (14)0.0016 (13)
C5A0.0516 (18)0.0347 (16)0.047 (2)0.0055 (13)0.0020 (15)0.0007 (14)
C6A0.0591 (19)0.0364 (17)0.0399 (19)0.0051 (14)0.0001 (15)0.0045 (14)
C7A0.0473 (17)0.0386 (17)0.0420 (19)0.0000 (13)0.0038 (14)0.0016 (14)
C8A0.065 (2)0.047 (2)0.051 (2)0.0009 (16)0.0064 (17)0.0036 (17)
O1B0.0780 (17)0.0470 (15)0.0581 (17)0.0102 (13)0.0189 (14)0.0041 (12)
N1B0.0554 (16)0.0384 (15)0.0470 (18)0.0003 (12)0.0082 (13)0.0054 (13)
C1B0.0532 (18)0.0379 (17)0.044 (2)0.0003 (14)0.0011 (15)0.0018 (14)
O2B0.0785 (17)0.0552 (16)0.0531 (16)0.0120 (13)0.0064 (13)0.0069 (13)
C2B0.0532 (19)0.0386 (17)0.051 (2)0.0076 (14)0.0013 (15)0.0009 (15)
C3B0.0526 (18)0.0347 (16)0.050 (2)0.0006 (14)0.0006 (15)0.0065 (15)
C4B0.0460 (16)0.0392 (17)0.0392 (19)0.0023 (13)0.0012 (13)0.0010 (14)
C5B0.057 (2)0.0424 (18)0.046 (2)0.0086 (15)0.0015 (15)0.0036 (15)
C6B0.064 (2)0.0388 (17)0.044 (2)0.0072 (15)0.0036 (16)0.0077 (15)
C7B0.0457 (17)0.053 (2)0.045 (2)0.0009 (15)0.0018 (14)0.0052 (16)
C8B0.060 (2)0.069 (3)0.052 (2)0.0099 (19)0.0092 (18)0.004 (2)
O1S0.0635 (15)0.0430 (14)0.0759 (19)0.0124 (11)0.0143 (13)0.0094 (13)
C1S0.075 (3)0.039 (2)0.083 (3)0.0006 (18)0.022 (2)0.0075 (19)
C2S0.056 (2)0.051 (2)0.057 (2)0.0035 (16)0.0065 (17)0.0052 (18)
O1T0.078 (3)0.032 (2)0.080 (3)0.009 (2)0.031 (2)0.012 (2)
C1T0.066 (4)0.033 (5)0.082 (5)0.012 (4)0.025 (3)0.007 (4)
C2T0.051 (3)0.033 (3)0.087 (5)0.010 (2)0.008 (3)0.003 (3)
O1U0.071 (8)0.036 (6)0.081 (9)0.013 (5)0.018 (6)0.002 (6)
C1U0.062 (11)0.033 (14)0.045 (9)0.008 (11)0.013 (7)0.018 (8)
C2U0.088 (13)0.044 (10)0.093 (14)0.009 (9)0.040 (10)0.007 (10)
Geometric parameters (Å, º) top
N1A—C7A1.338 (4)C4B—C5B1.380 (5)
N1A—C4A1.416 (4)C5B—C6B1.381 (5)
N1A—H1A0.8700C5B—H5B0.9400
O1A—C1A1.366 (4)C6B—H6B0.9400
O1A—H11A0.8300C7B—C8B1.489 (5)
C1A—C2A1.387 (5)C8B—H8B10.9700
C1A—C6A1.392 (5)C8B—H8B20.9700
O2A—C7A1.241 (4)C8B—H8B30.9700
C2A—C3A1.381 (5)O1S—C1S1.415 (5)
C2A—H2A0.9400O1S—C2S1.428 (5)
C3A—C4A1.388 (4)C1S—C2Si1.485 (5)
C3A—H3A0.9400C1S—H1S10.9800
C4A—C5A1.400 (5)C1S—H1S20.9800
C5A—C6A1.369 (5)C2S—C1Si1.485 (5)
C5A—H5A0.9400C2S—H2S10.9800
C6A—H6A0.9400C2S—H2S20.9800
C7A—C8A1.496 (5)O1T—C2T1.413 (7)
C8A—H8A10.9700O1T—C1T1.442 (7)
C8A—H8A20.9700C1T—C2Tii1.473 (13)
C8A—H8A30.9700C1T—H1T10.9800
O1B—C1B1.358 (4)C1T—H1T20.9800
O1B—H11B0.8300C2T—C1Tii1.473 (13)
N1B—C7B1.330 (5)C2T—H2T10.9800
N1B—C4B1.429 (4)C2T—H2T20.9800
N1B—H1B0.8700O1U—C2U1.43 (2)
C1B—C2B1.378 (5)O1U—C1U1.45 (3)
C1B—C6B1.388 (5)C1U—C2Uii1.48 (3)
O2B—C7B1.241 (4)C1U—H1U10.9800
C2B—C3B1.382 (5)C1U—H1U20.9800
C2B—H2B0.9400C2U—C1Uii1.48 (3)
C3B—C4B1.386 (5)C2U—H2U10.9800
C3B—H3B0.9400C2U—H2U20.9800
C7A—N1A—C4A125.7 (3)C5B—C6B—H6B119.7
C7A—N1A—H1A117.2C1B—C6B—H6B119.7
C4A—N1A—H1A117.2O2B—C7B—N1B121.7 (3)
C1A—O1A—H11A109.5O2B—C7B—C8B121.7 (3)
O1A—C1A—C2A118.5 (3)N1B—C7B—C8B116.6 (3)
O1A—C1A—C6A121.8 (3)C7B—C8B—H8B1109.5
C2A—C1A—C6A119.7 (3)C7B—C8B—H8B2109.5
C3A—C2A—C1A119.8 (3)H8B1—C8B—H8B2109.5
C3A—C2A—H2A120.1C7B—C8B—H8B3109.5
C1A—C2A—H2A120.1H8B1—C8B—H8B3109.5
C2A—C3A—C4A120.9 (3)H8B2—C8B—H8B3109.5
C2A—C3A—H3A119.6C1S—O1S—C2S110.4 (3)
C4A—C3A—H3A119.6O1S—C1S—C2Si111.3 (3)
C3A—C4A—C5A118.7 (3)O1S—C1S—H1S1109.4
C3A—C4A—N1A119.8 (3)C2Si—C1S—H1S1109.4
C5A—C4A—N1A121.5 (3)O1S—C1S—H1S2109.4
C6A—C5A—C4A120.6 (3)C2Si—C1S—H1S2109.4
C6A—C5A—H5A119.7H1S1—C1S—H1S2108.0
C4A—C5A—H5A119.7O1S—C2S—C1Si110.3 (3)
C5A—C6A—C1A120.3 (3)O1S—C2S—H2S1109.6
C5A—C6A—H6A119.9C1Si—C2S—H2S1109.6
C1A—C6A—H6A119.9O1S—C2S—H2S2109.6
O2A—C7A—N1A122.1 (3)C1Si—C2S—H2S2109.6
O2A—C7A—C8A121.5 (3)H2S1—C2S—H2S2108.1
N1A—C7A—C8A116.4 (3)C2T—O1T—C1T110.2 (6)
C7A—C8A—H8A1109.5O1T—C1T—C2Tii111.2 (8)
C7A—C8A—H8A2109.5O1T—C1T—H1T1109.4
H8A1—C8A—H8A2109.5C2Tii—C1T—H1T1109.4
C7A—C8A—H8A3109.5O1T—C1T—H1T2109.4
H8A1—C8A—H8A3109.5C2Tii—C1T—H1T2109.4
H8A2—C8A—H8A3109.5H1T1—C1T—H1T2108.0
C1B—O1B—H11B109.5O1T—C2T—C1Tii109.8 (6)
C7B—N1B—C4B125.6 (3)O1T—C2T—H2T1109.7
C7B—N1B—H1B117.2C1Tii—C2T—H2T1109.7
C4B—N1B—H1B117.2O1T—C2T—H2T2109.7
O1B—C1B—C2B118.7 (3)C1Tii—C2T—H2T2109.7
O1B—C1B—C6B122.6 (3)H2T1—C2T—H2T2108.2
C2B—C1B—C6B118.7 (3)C2U—O1U—C1U109.6 (19)
C1B—C2B—C3B121.0 (3)O1U—C1U—C2Uii108 (2)
C1B—C2B—H2B119.5O1U—C1U—H1U1110.1
C3B—C2B—H2B119.5C2Uii—C1U—H1U1110.1
C2B—C3B—C4B119.9 (3)O1U—C1U—H1U2110.1
C2B—C3B—H3B120.0C2Uii—C1U—H1U2110.1
C4B—C3B—H3B120.0H1U1—C1U—H1U2108.5
C5B—C4B—C3B119.4 (3)O1U—C2U—C1Uii110 (2)
C5B—C4B—N1B121.6 (3)O1U—C2U—H2U1109.7
C3B—C4B—N1B119.0 (3)C1Uii—C2U—H2U1109.7
C4B—C5B—C6B120.3 (3)O1U—C2U—H2U2109.7
C4B—C5B—H5B119.9C1Uii—C2U—H2U2109.7
C6B—C5B—H5B119.9H2U1—C2U—H2U2108.2
C5B—C6B—C1B120.6 (3)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+2, y1, z+2.
(pardmp) top
Crystal data top
2[C8H9NO2][C6H14N2]F(000) = 448
Mr = 416.52Dx = 1.258 Mg m3
Dm = 0 Mg m3
Dm measured by not measured
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.6970 (9) ÅCell parameters from 3488 reflections
b = 11.0240 (9) Åθ = 2.5–29°
c = 9.4896 (8) ŵ = 0.09 mm1
β = 100.684 (2)°T = 150 K
V = 1099.65 (16) Å3Plate, colourless
Z = 20.56 × 0.18 × 0.08 mm
Data collection top
CCD area detector
diffractometer
2724 independent reflections
Radiation source: fine-focus sealed tube2512 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
phi and ω scansθmax = 29.1°, θmin = 1.9°
Absorption correction: multi-scan
SADABS
h = 814
Tmin = 0.833, Tmax = 1k = 1514
7034 measured reflectionsl = 1212
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: geom/difmap
wR(F2) = 0.134Riding/refall
S = 1.06 w = 1/[σ2(Fo2) + (0.069P)2 + 0.4625P]
where P = (Fo2 + 2Fc2)/3
2724 reflections(Δ/σ)max = 0.009
146 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
2[C8H9NO2][C6H14N2]V = 1099.65 (16) Å3
Mr = 416.52Z = 2
Monoclinic, P21/cMo Kα radiation
a = 10.6970 (9) ŵ = 0.09 mm1
b = 11.0240 (9) ÅT = 150 K
c = 9.4896 (8) Å0.56 × 0.18 × 0.08 mm
β = 100.684 (2)°
Data collection top
CCD area detector
diffractometer
2724 independent reflections
Absorption correction: multi-scan
SADABS
2512 reflections with I > 2σ(I)
Tmin = 0.833, Tmax = 1Rint = 0.016
7034 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.134Riding/refall
S = 1.06Δρmax = 0.40 e Å3
2724 reflectionsΔρmin = 0.19 e Å3
146 parameters
Special details top

Experimental. INTENSITY STATISTICS FOR DATASET # 1 IOGRIM.hkl

Resolution #Data #Theory %Complete Redundancy Mean I Mean I/s R(int) R(sigma)

Inf - 2.10 144 144 100.0 3.46 581.6 74.12 0.0129 0.0097 2.10 - 1.65 146 147 99.3 3.77 225.9 71.37 0.0097 0.0096 1.65 - 1.40 171 172 99.4 3.53 90.0 49.30 0.0167 0.0133 1.40 - 1.25 190 191 99.5 3.23 71.2 40.93 0.0204 0.0158 1.25 - 1.15 169 169 100.0 2.93 81.0 35.07 0.0170 0.0173 1.15 - 1.05 246 246 100.0 2.79 65.6 32.48 0.0201 0.0197 1.05 - 1.00 159 159 100.0 2.55 47.0 26.68 0.0222 0.0248 1.00 - 0.95 203 203 100.0 2.50 28.1 19.40 0.0290 0.0322 0.95 - 0.90 247 248 99.6 2.32 28.5 17.70 0.0349 0.0360 0.90 - 0.85 303 304 99.7 2.14 18.8 14.17 0.0414 0.0479 0.85 - 0.80 397 399 99.5 2.06 15.2 12.07 0.0438 0.0590 0.80 - 0.75 431 500 86.2 1.50 14.0 10.48 0.0510 0.0732 0.75 - 0.73 55 206 26.7 0.31 12.5 8.07 0.1458 0.0856 —————————————————————————— 0.85 - 0.73 883 1105 79.9 1.48 14.4 11.05 0.0470 0.0671 Inf - 0.73 2861 3088 92.6 2.34 74.8 27.20 0.0164 0.0180

Merged [A], lowest resolution = 11.02 Angstroms, 119 outliers downweighted

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. TITL pardmp in P2(1)/c CELL 0.71073 10.6970 11.0240 9.4896 90.000 100.684 90.000 ZERR 2.00 0.0009 0.0009 0.0008 0.000 0.002 0.000 L A T T 1 SYMM –X, 0.5+Y, 0.5-Z SFAC C H N O UNIT 44 64 8 8 TEMP -123 L·S. 4 BOND $H FMAP 2 PLAN 10

HTAB EQIV $1 x, -y + 1/2, z - 1/2 EQIV $2 - x + 1, -y, -z RTAB D1 H1 O2_$1 RTAB D2 H11 N1S_$2 MPLA 6 C1 C2 C3 C4 C5 C6 MPLA 6 N1 C7 C8 O2 ACTA rem EXTI 0.000000 W GH T 0.069000 0.462500 FVAR 0.70905 O1 4 0.287803 - 0.313197 0.046738 11.00000 0.03591 0.01850 = 0.04325 0.00172 0.01506 0.00627 H11 2 0.355684 - 0.327695 - 0.008941 11.00000 0.05999 C1 1 0.253916 - 0.193647 0.039961 11.00000 0.02476 0.01899 = 0.02826 - 0.00196 0.00326 0.00305 C2 1 0.293258 - 0.112732 - 0.055069 11.00000 0.03577 0.02603 = 0.02992 - 0.00084 0.01521 0.00773 AFIX 43 H2 2 0.345254 - 0.140057 - 0.119682 11.00000 - 1.20000 AFIX 0 C3 1 0.256667 0.008034 - 0.055719 11.00000 0.03655 0.02324 = 0.02526 0.00454 0.01388 0.00459 AFIX 43 H3 2 0.285291 0.063189 - 0.119818 11.00000 - 1.20000 AFIX 0 C4 1 0.178674 0.049506 0.036134 11.00000 0.02291 0.01813 = 0.01828 - 0.00131 0.00325 0.00229 C5 1 0.138037 - 0.031979 0.129900 11.00000 0.02416 0.02204 = 0.02419 - 0.00052 0.00886 0.00230 AFIX 43 H5 2 0.084159 - 0.005076 0.192690 11.00000 - 1.20000 AFIX 0 C6 1 0.175851 - 0.152525 0.132188 11.00000 0.02707 0.02047 = 0.02790 0.00340 0.00903 - 0.00013 AFIX 43 H6 2 0.148240 - 0.207457 0.197230 11.00000 - 1.20000 AFIX 0 N1 3 0.138425 0.172399 0.022781 11.00000 0.02859 0.01827 = 0.01630 0.00176 0.00683 0.00330 H1 2 0.130376 0.203763 - 0.062325 11.00000 0.03103 C7 1 0.109786 0.243270 0.127197 11.00000 0.02715 0.02017 = 0.02122 - 0.00131 0.00611 0.00120 O2 4 0.122829 0.210691 0.253383 11.00000 0.06089 0.02583 = 0.01837 - 0.00079 0.01143 0.00611 C8 1 0.059225 0.367091 0.079398 11.00000 0.03916 0.02041 = 0.02717 - 0.00036 0.00970 0.00647 AFIX 137 H8A 2 - 0.032780 0.369318 0.076658 11.00000 - 1.50000 H8B 2 0.076635 0.384092 - 0.016477 11.00000 - 1.50000 H8C 2 0.100937 0.428392 0.146927 11.00000 - 1.50000 AFIX 0 N1S 3 0.504218 0.383733 0.070207 11.00000 0.02565 0.01714 = 0.02468 0.00119 0.00603 0.00211 C1S 1 0.454026 0.296594 0.161968 11.00000 0.03350 0.02520 = 0.03580 0.00511 0.01252 0.00215 AFIX 137 H1S1 2 0.428362 0.222268 0.107598 11.00000 - 1.50000 H1S2 2 0.380164 0.331802 0.194469 11.00000 - 1.50000 H1S3 2 0.519949 0.277371 0.245272 11.00000 - 1.50000 AFIX 0 C2S 1 0.542160 0.496096 0.150533 11.00000 0.02778 0.02244 = 0.02150 - 0.00309 0.00209 0.00274 AFIX 23 H2S1 2 0.608235 0.477646 0.235526 11.00000 - 1.20000 H2S2 2 0.467794 0.531182 0.184355 11.00000 - 1.20000 AFIX 0 C3S 1 0.406523 0.413259 - 0.056138 11.00000 0.02474 0.02065 = 0.02679 - 0.00442 0.00323 - 0.00025 AFIX 23 H3S1 2 0.330702 0.447495 - 0.024566 11.00000 - 1.20000 H3S2 2 0.380349 0.338399 - 0.111410 11.00000 - 1.20000

HKLF 4

REM pardmp in P2(1)/c REM R1 = 0.0525 for 2512 Fo > 4sig(Fo) and 0.0563 for all 2724 data REM 146 parameters refined using 0 restraints

END

WGHT 0.0697 0.4431 REM Highest difference peak 0.401, deepest hole -0.193, 1-σ level 0.053 Q1 1 0.2025 0.0215 - 0.0190 11.00000 0.05 0.40 Q2 1 0.2179 - 0.1657 0.0875 11.00000 0.05 0.39 Q3 1 0.5604 0.3383 0.0447 11.00000 0.05 0.37 Q4 1 0.0781 0.3047 0.0979 11.00000 0.05 0.36 Q5 1 0.4324 0.4564 - 0.0962 11.00000 0.05 0.34 Q6 1 0.1596 0.0076 0.0774 11.00000 0.05 0.34 Q7 1 0.1715 0.1173 0.0476 11.00000 0.05 0.33 Q8 1 0.2963 - 0.0460 - 0.0221 11.00000 0.05 0.33 Q9 1 0.1422 0.2121 0.0777 11.00000 0.05 0.31 Q10 1 0.5286 0.4415 0.1047 11.00000 0.05 0.31

#=============================================================================== # PLATON/CHECK-(191101) versus check.def version of 16/11/01 for entry: pardmp # Data From: pardmp.cif - Data Type: CIF Bond Precision C—C = 0.0019 A # # CELL 0.71073 10.697 11.024 9.490 90.00 100.68 90.00 1099.65 # SpaceGroup from Symmetry P21/c Hall: –P 2ybc # Reported P21/c ? # MoietyFormula C8 H9 N O2, 0.5(C6 H14 N2) # Reported ? # SumFormula C11 H16 N2 O2 # Reported C22 H32 N4 O4 # Mr = 208.26[Calc], 416.52[Rep] # Dx,gcm-3 = 1.258[Calc], 1.258[Rep] # Z = 4[Calc], 2[Rep] # Mu (mm-1) = 0.088[Calc], 0.088[Rep] # F000 = 448.0[Calc], 448.0[Rep] # Reported T limits: Tmin=0.833 Tmax=1.000 'MULTISCAN' # Calculated T limits: Tmin=0.981 Tmin'=0.952 Tmax=0.993 # Reported Hmax= 14, Kmax= 15, Lmax= 12, Nref= 2724, Th(max)= 29.08 # Calculated Hmax= 14, Kmax= 15, Lmax= 12, Nref= 2931 (2931), Ratio= 0.93 (0.93) # R= 0.0525 (2512), wR2= 0.1339 (2724), S = 1.059, Npar= 146 #=============================================================================== >>> The Following ALERTS were generated <<<

041_ALERT C Calc. and Rep. SumFormula Strings Differ.. ? 045_ALERT C Calculated and Reported Z differ by ·········. 2.00 Ratio

Z=2 description used throughout this series.

061_ALERT C Tmax/Tmin Range Test RR' too large ·········.. 0.87

SADABS corrects for all systematic errors, not just crystal absorption. Extra absorption may come from glue, glass fibre etc.

125_ALERT C No _symmetry_space_group_name_Hall given ···.. ?

-P 2ybc

145_ALERT C su on beta Small or Missing (x 10000) ··· 20 Deg.

This is value produced by the Saint integration software. I think cell parameter s.u.s often seem unrealistically small with area detector data.

ALERT Level Summary 6 ALERT Level C = Check & Explain

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.28780 (10)0.31320 (9)0.04674 (12)0.0316 (3)
H110.356 (2)0.328 (2)0.009 (2)0.060 (6)*
C10.25392 (13)0.19365 (11)0.03996 (15)0.0242 (3)
C20.29326 (14)0.11273 (13)0.05507 (16)0.0294 (3)
H20.34530.14010.11970.035*
C30.25667 (14)0.00803 (12)0.05572 (15)0.0273 (3)
H30.28530.06320.11980.033*
C40.17867 (12)0.04951 (11)0.03613 (13)0.0198 (3)
C50.13804 (12)0.03198 (12)0.12990 (14)0.0229 (3)
H50.08420.00510.19270.027*
C60.17585 (13)0.15253 (12)0.13219 (15)0.0246 (3)
H60.14820.20750.19720.030*
N10.13842 (11)0.17240 (9)0.02278 (12)0.0207 (2)
H10.1304 (17)0.2038 (16)0.062 (2)0.031 (4)*
C70.10979 (12)0.24327 (12)0.12720 (14)0.0226 (3)
O20.12283 (12)0.21069 (9)0.25338 (10)0.0345 (3)
C80.05923 (15)0.36709 (12)0.07940 (15)0.0285 (3)
H8A0.03280.36930.07670.043*
H8B0.07660.38410.01650.043*
H8C0.10090.42840.14690.043*
N1S0.50422 (10)0.38373 (9)0.07021 (12)0.0223 (2)
C1S0.45403 (14)0.29659 (13)0.16197 (17)0.0307 (3)
H1S10.42840.22230.10760.046*
H1S20.38020.33180.19450.046*
H1S30.51990.27740.24530.046*
C2S0.54216 (13)0.49610 (12)0.15053 (14)0.0242 (3)
H2S10.60820.47760.23550.029*
H2S20.46780.53120.18440.029*
C3S0.40652 (12)0.41326 (12)0.05614 (14)0.0243 (3)
H3S10.33070.44750.02460.029*
H3S20.38030.33840.11140.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0359 (6)0.0185 (5)0.0432 (6)0.0063 (4)0.0151 (5)0.0017 (4)
C10.0248 (6)0.0190 (6)0.0283 (7)0.0030 (5)0.0033 (5)0.0020 (5)
C20.0358 (7)0.0260 (7)0.0299 (7)0.0077 (5)0.0152 (6)0.0008 (5)
C30.0365 (7)0.0232 (6)0.0253 (7)0.0046 (5)0.0139 (5)0.0045 (5)
C40.0229 (6)0.0181 (6)0.0183 (6)0.0023 (4)0.0032 (4)0.0013 (4)
C50.0242 (6)0.0220 (6)0.0242 (6)0.0023 (5)0.0089 (5)0.0005 (5)
C60.0271 (6)0.0205 (6)0.0279 (7)0.0001 (5)0.0090 (5)0.0034 (5)
N10.0286 (5)0.0183 (5)0.0163 (5)0.0033 (4)0.0068 (4)0.0018 (4)
C70.0272 (6)0.0202 (6)0.0212 (6)0.0012 (5)0.0061 (5)0.0013 (5)
O20.0609 (7)0.0258 (5)0.0184 (5)0.0061 (5)0.0114 (5)0.0008 (4)
C80.0392 (8)0.0204 (6)0.0272 (7)0.0065 (5)0.0097 (6)0.0004 (5)
N1S0.0256 (5)0.0171 (5)0.0247 (5)0.0021 (4)0.0060 (4)0.0012 (4)
C1S0.0335 (7)0.0252 (7)0.0358 (8)0.0022 (5)0.0125 (6)0.0051 (6)
C2S0.0278 (6)0.0224 (6)0.0215 (6)0.0027 (5)0.0021 (5)0.0031 (5)
C3S0.0247 (6)0.0207 (6)0.0268 (7)0.0002 (5)0.0032 (5)0.0044 (5)
Geometric parameters (Å, º) top
O1—C11.3652 (15)C7—C81.5068 (18)
O1—H110.99 (2)C8—H8A0.9800
C1—C21.388 (2)C8—H8B0.9800
C1—C61.3928 (19)C8—H8C0.9800
C2—C31.3874 (19)N1S—C1S1.4638 (17)
C2—H20.9500N1S—C2S1.4715 (16)
C3—C41.3909 (18)N1S—C3S1.4734 (17)
C3—H30.9500C1S—H1S10.9800
C4—C51.3896 (18)C1S—H1S20.9800
C4—N11.4201 (16)C1S—H1S30.9800
C5—C61.3881 (18)C2S—C3Si1.5115 (19)
C5—H50.9500C2S—H2S10.9900
C6—H60.9500C2S—H2S20.9900
N1—C71.3411 (16)C3S—C2Si1.5115 (19)
N1—H10.868 (19)C3S—H3S10.9900
C7—O21.2331 (16)C3S—H3S20.9900
C1—O1—H11110.3 (13)C7—C8—H8B109.5
O1—C1—C2122.76 (12)H8A—C8—H8B109.5
O1—C1—C6118.00 (12)C7—C8—H8C109.5
C2—C1—C6119.24 (12)H8A—C8—H8C109.5
C3—C2—C1120.02 (12)H8B—C8—H8C109.5
C3—C2—H2120.0C1S—N1S—C2S109.91 (11)
C1—C2—H2120.0C1S—N1S—C3S110.24 (11)
C2—C3—C4120.94 (12)C2S—N1S—C3S108.75 (10)
C2—C3—H3119.5N1S—C1S—H1S1109.5
C4—C3—H3119.5N1S—C1S—H1S2109.5
C5—C4—C3118.95 (11)H1S1—C1S—H1S2109.5
C5—C4—N1123.24 (11)N1S—C1S—H1S3109.5
C3—C4—N1117.70 (11)H1S1—C1S—H1S3109.5
C6—C5—C4120.27 (11)H1S2—C1S—H1S3109.5
C6—C5—H5119.9N1S—C2S—C3Si110.19 (10)
C4—C5—H5119.9N1S—C2S—H2S1109.6
C5—C6—C1120.58 (12)C3Si—C2S—H2S1109.6
C5—C6—H6119.7N1S—C2S—H2S2109.6
C1—C6—H6119.7C3Si—C2S—H2S2109.6
C7—N1—C4126.64 (11)H2S1—C2S—H2S2108.1
C7—N1—H1117.3 (12)N1S—C3S—C2Si110.34 (10)
C4—N1—H1116.1 (12)N1S—C3S—H3S1109.6
O2—C7—N1123.20 (12)C2Si—C3S—H3S1109.6
O2—C7—C8121.73 (12)N1S—C3S—H3S2109.6
N1—C7—C8115.07 (11)C2Si—C3S—H3S2109.6
C7—C8—H8A109.5H3S1—C3S—H3S2108.1
Symmetry code: (i) x+1, y+1, z.
(parnmm) Paracetamol hemi(N-Methylmorpholine) top
Crystal data top
2[C8H9NO2][C5H11NO]F(000) = 432
Mr = 403.47Dx = 1.248 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.5749 (8) ÅCell parameters from 2729 reflections
b = 11.0221 (8) Åθ = 5–55°
c = 9.3894 (7) ŵ = 0.09 mm1
β = 101.145 (2)°T = 150 K
V = 1073.77 (14) Å3Rod, colourless
Z = 20.34 × 0.09 × 0.07 mm
Data collection top
Radiation source: fine-focus sealed tube1890 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
phi and ω scansθmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan
SADABS
h = 1313
Tmin = 0.792, Tmax = 0.962k = 1414
6517 measured reflectionsl = 1112
2444 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: geom/difmap
R[F2 > 2σ(F2)] = 0.041Riding/refall
wR(F2) = 0.108 w = 1/[σ2(Fo2) + (0.0658P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max < 0.001
2444 reflectionsΔρmax = 0.22 e Å3
147 parametersΔρmin = 0.22 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.008 (3)
Crystal data top
2[C8H9NO2][C5H11NO]V = 1073.77 (14) Å3
Mr = 403.47Z = 2
Monoclinic, P21/cMo Kα radiation
a = 10.5749 (8) ŵ = 0.09 mm1
b = 11.0221 (8) ÅT = 150 K
c = 9.3894 (7) Å0.34 × 0.09 × 0.07 mm
β = 101.145 (2)°
Data collection top
Absorption correction: multi-scan
SADABS
2444 independent reflections
Tmin = 0.792, Tmax = 0.9621890 reflections with I > 2σ(I)
6517 measured reflectionsRint = 0.022
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.108Riding/refall
S = 0.97Δρmax = 0.22 e Å3
2444 reflectionsΔρmin = 0.22 e Å3
147 parameters
Special details top

Experimental. INTENSITY STATISTICS FOR DATASET # 1 IOSMEL.hkl

Resolution #Data #Theory %Complete Redundancy Mean I Mean I/s R(int) R(sigma)

Inf - 2.10 139 140 99.3 3.31 178.5 89.37 0.0129 0.0058 2.10 - 1.65 143 143 100.0 3.62 76.0 56.11 0.0185 0.0116 1.65 - 1.40 171 171 100.0 3.50 25.5 28.45 0.0288 0.0232 1.40 - 1.25 180 180 100.0 3.21 19.5 20.88 0.0321 0.0328 1.25 - 1.15 171 171 100.0 2.94 24.4 19.73 0.0254 0.0289 1.15 - 1.05 237 238 99.6 2.81 16.9 16.54 0.0299 0.0409 1.05 - 1.00 162 162 100.0 2.55 12.8 13.12 0.0325 0.0538 1.00 - 0.95 200 200 100.0 2.44 7.6 8.68 0.0365 0.0799 0.95 - 0.90 236 238 99.2 2.28 7.9 7.71 0.0393 0.0832 0.90 - 0.85 288 290 99.3 2.17 4.5 5.42 0.0591 0.1313 0.85 - 0.80 374 383 97.7 1.99 3.6 4.53 0.0656 0.1677 0.80 - 0.77 278 289 96.2 1.83 3.4 4.12 0.0747 0.1833 —————————————————————————— 0.90 - 0.77 940 962 97.7 1.99 3.8 4.68 0.0651 0.1586 Inf - 0.77 2579 2605 99.0 2.57 23.6 18.01 0.0222 0.0285

Merged [A], lowest resolution = 11.02 Angstroms, 101 outliers downweighted

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. TITL Parnmm in P2(1)/c CELL 0.71073 10.5749 11.0221 9.3894 90.000 101.145 90.000 ZERR 2.00 0.0008 0.0008 0.0007 0.000 0.002 0.000 L A T T 1 SYMM –X, 0.5+Y, 0.5-Z SFAC C H N O UNIT 42 58 6 10 TEMP -123 ACTA L·S. 4 BOND $H FMAP 2 PLAN 20

EXYZ N1S O1S EADP N1S O1S HTAB EQIV $1 - x + 1, -y + 2, -z EQIV $2 x, -y + 3/2, z - 1/2 RTAB D1 H11 O1S_$1 RTAB D2 H11 N1S_$1 RTAB D3 H1 O2_$2 MPLA 6 C1 C2 C3 C4 C5 C6 MPLA 4 N1 C7 O2 C8 WGHT 0.065800 EXTI 0.007550 FVAR 0.42214 O1 4 0.779633 1.316736 0.043176 11.00000 0.04252 0.02513 = 0.05311 - 0.00015 0.01385 - 0.01016 H11 2 0.841894 1.329974 - 0.010162 11.00000 0.07181 C1 1 0.751223 1.195380 0.038784 11.00000 0.02978 0.02529 = 0.03242 0.00222 0.00093 - 0.00561 C2 1 0.796125 1.115391 - 0.054012 11.00000 0.04298 0.03346 = 0.03162 0.00115 0.01429 - 0.01240 AFIX 43 H2 2 0.849256 1.143976 - 0.117705 11.00000 - 1.20000 AFIX 0 C3 1 0.763412 0.993797 - 0.053707 11.00000 0.04161 0.03034 = 0.02576 - 0.00381 0.01229 - 0.00644 AFIX 43 H3 2 0.795689 0.939182 - 0.116356 11.00000 - 1.20000 AFIX 0 C4 1 0.684235 0.950485 0.036666 11.00000 0.02762 0.02359 = 0.02050 0.00167 0.00166 - 0.00387 C5 1 0.638575 1.031332 0.128652 11.00000 0.02588 0.02802 = 0.02727 0.00086 0.00695 - 0.00377 AFIX 43 H5 2 0.583771 1.003246 0.190766 11.00000 - 1.20000 AFIX 0 C6 1 0.672823 1.152791 0.129938 11.00000 0.02841 0.02560 = 0.03242 - 0.00278 0.00557 - 0.00049 AFIX 43 H6 2 0.642188 1.207275 0.193982 11.00000 - 1.20000 AFIX 0 N1 3 0.646349 0.826745 0.023861 11.00000 0.03319 0.02387 = 0.01853 - 0.00203 0.00635 - 0.00526 H1 2 0.638203 0.793587 - 0.062743 11.00000 0.03332 C7 1 0.616536 0.756216 0.128714 11.00000 0.03108 0.02500 = 0.02250 0.00130 0.00575 - 0.00065 O2 4 0.627776 0.790081 0.255375 11.00000 0.07692 0.03062 = 0.02001 0.00027 0.01221 - 0.00675 C8 1 0.567316 0.631693 0.081331 11.00000 0.03846 0.02533 = 0.02901 0.00121 0.00871 - 0.00500 AFIX 137 H8A 2 0.584398 0.614745 - 0.015656 11.00000 - 1.50000 H8B 2 0.474304 0.628016 0.078728 11.00000 - 1.50000 H8C 2 0.611181 0.571200 0.150053 11.00000 - 1.50000 AFIX 0

PART -1 N1S 3 0.008020 0.616152 0.070088 10.50000 0.03356 0.03741 = 0.05243 0.00880 0.00163 - 0.00884 C3S 1 - 0.041956 0.695577 0.145519 10.50000 0.03010 0.04200 = 0.05422 - 0.01122 0.01384 - 0.00382 AFIX 137 H3S1 2 - 0.062663 0.769735 0.088174 10.50000 - 1.50000 H3S2 2 0.019946 0.714472 0.234644 10.50000 - 1.50000 H3S3 2 - 0.120804 0.662360 0.170568 10.50000 - 1.50000 AFIX 0 PART -2 O1S 4 0.008020 0.616152 0.070088 10.50000 0.03356 0.03741 = 0.05243 0.00880 0.00163 - 0.00884 PART 0 C1S 1 - 0.084237 0.590874 - 0.064218 11.00000 0.03586 0.04519 = 0.06622 0.02238 - 0.00952 - 0.00542 AFIX 23 H1SA 2 - 0.101257 0.666327 - 0.121941 11.00000 - 1.20000 H1SB 2 - 0.166667 0.563143 - 0.040202 11.00000 - 1.20000 AFIX 0 C2S 1 0.034362 0.503677 0.151931 11.00000 0.04050 0.05242 = 0.04591 0.01779 - 0.00685 - 0.01665 AFIX 23 H2SA 2 - 0.045765 0.474331 0.180212 11.00000 - 1.20000 H2SB 2 0.098636 0.519069 0.241728 11.00000 - 1.20000

HKLF 4

REM Parnmm in P2(1)/c REM R1 = 0.0408 for 1890 Fo > 4sig(Fo) and 0.0515 for all 2444 data REM 147 parameters refined using 0 restraints

END

WGHT 0.0663 0.0000 REM Highest difference peak 0.216, deepest hole -0.220, 1-σ level 0.040 Q1 1 0.8070 1.1545 0.0230 11.00000 0.05 0.22 Q2 1 0.6926 0.9842 0.1154 11.00000 0.05 0.20 Q3 1 0.7491 0.9617 0.0202 11.00000 0.05 0.19 Q4 1 0.7466 1.1628 0.1120 11.00000 0.05 0.19 Q5 1 0.6977 0.9781 - 0.0292 11.00000 0.05 0.19 Q6 1 0.6326 0.9977 0.0517 11.00000 0.05 0.19 Q7 1 0.6585 0.8993 0.0331 11.00000 0.05 0.18 Q8 1 0.6814 1.0844 0.1391 11.00000 0.05 0.18 Q9 1 0.5968 0.6936 0.1031 11.00000 0.05 0.17 Q10 1 - 0.0046 0.5610 0.1324 11.00000 0.05 0.17 Q11 1 0.6977 1.1752 0.0647 11.00000 0.05 0.16 Q12 1 0.6533 1.0930 0.1215 11.00000 0.05 0.16 Q13 1 0.0406 0.4595 0.0906 11.00000 0.05 0.16 Q14 1 0.6350 0.7396 0.3186 11.00000 0.05 0.15 Q15 1 0.5580 0.5870 0.1741 11.00000 0.05 0.15 Q16 1 0.6619 0.7889 0.0925 11.00000 0.05 0.15 Q17 1 0.7597 0.9445 - 0.1375 11.00000 0.05 0.14 Q18 1 0.7562 1.1572 - 0.0264 11.00000 0.05 0.14 Q19 1 0.0177 0.6386 0.1536 11.00000 0.05 0.14 Q20 1 0.6032 0.7990 0.0608 11.00000 0.05 0.13

Checkcif oputput: #=============================================================================== # PLATON/CHECK-(191101) versus check.def version of 16/11/01 for entry: parnmm # Data From: parnmm.cif - Data Type: CIF Bond Precision C—C = 0.0017 A # # CELL 0.71073 10.575 11.022 9.389 90.00 101.14 90.00 1073.77 # SpaceGroup from Symmetry P21/c Hall: –P 2ybc # Reported P21/c ? # MoietyFormula C8 H9 N O2, 0.5(C5 H11 N O) # Reported 2[C8H9NO2][C5H11NO] # SumFormula C11 H15 N2 O3 # Reported C21 H29 N3 O5 # Mr = 201.74[Calc], 403.47[Rep] # Dx,gcm-3 = 1.248[Calc], 1.248[Rep] # Z = 4[Calc], 2[Rep] # Mu (mm-1) = 0.090[Calc], 0.090[Rep] # F000 = 432.0[Calc], 432.0[Rep] # Reported T limits: Tmin=0.792 Tmax=0.962 'MULTISCAN' # Calculated T limits: Tmin=0.990 Tmin'=0.970 Tmax=0.994 # Reported Hmax= 13, Kmax= 14, Lmax= 12, Nref= 2444, Th(max)= 27.49 # Calculated Hmax= 13, Kmax= 14, Lmax= 12, Nref= 2466 (2466), Ratio= 0.99 (0.99) # R= 0.0408 (1890), wR2= 0.1082 (2444), S = 0.973, Npar= 147 #=============================================================================== >>> The Following ALERTS were generated <<<

030_ALERT C Refined Extinction parameter within range ···. 2.67 Sigma

This is a rounding error problem: Actual data are: 0.00755 0.00253 0.000 EXTI which corresponds to σ.

041_ALERT C Calc. and Rep. SumFormula Strings Differ.. ? 042_ALERT C Calc. and Rep. MoietyFormula Strings Differ.. ? 045_ALERT C Calculated and Reported Z differ by ·········. 2.00 Ratio

This is because of checkcif's choice of moiety formula. We prefer the Z=2 description.

061_ALERT C Tmax/Tmin Range Test RR' too large ·········.. 0.84 062_ALERT C Rescale T(min) & T(max) by ··················. 1.03

SADABS corrects for all systematic errors, not just crystal absorption. Extra absorption may come from glue, glass fibre etc.

125_ALERT C No _symmetry_space_group_name_Hall given ···.. ?

-P 2ybc

145_ALERT C su on beta Small or Missing (x 10000) ··· 20 Deg.

This is value produced by the Saint integration software. I think cell parameter s.u.s often seem unrealistically small with area detector data.

302_ALERT C Anion/Solvent Disorder ·····················.. 28.00 Perc.

See text.

ALERT Level Summary 9 ALERT Level C = Check & Explain #===============================================================================

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.77963 (10)1.31674 (8)0.04318 (11)0.0396 (3)
H110.842 (2)1.3300 (16)0.010 (2)0.072 (6)*
C10.75122 (12)1.19538 (11)0.03878 (14)0.0298 (3)
C20.79612 (13)1.11539 (11)0.05401 (14)0.0351 (3)
H20.84931.14400.11770.042*
C30.76341 (13)0.99380 (11)0.05371 (13)0.0318 (3)
H30.79570.93920.11640.038*
C40.68423 (11)0.95049 (10)0.03667 (12)0.0243 (3)
C50.63857 (11)1.03133 (10)0.12865 (13)0.0268 (3)
H50.58381.00320.19080.032*
C60.67282 (11)1.15279 (11)0.12994 (13)0.0289 (3)
H60.64221.20730.19400.035*
N10.64635 (10)0.82675 (9)0.02386 (11)0.0250 (2)
H10.6382 (14)0.7936 (12)0.0627 (17)0.033 (4)*
C70.61654 (11)0.75622 (10)0.12871 (13)0.0261 (3)
O20.62778 (11)0.79008 (8)0.25537 (9)0.0421 (3)
C80.56732 (12)0.63169 (11)0.08133 (14)0.0306 (3)
H8A0.58440.61470.01570.046*
H8B0.47430.62800.07870.046*
H8C0.61120.57120.15010.046*
N1S0.00802 (10)0.61615 (9)0.07009 (12)0.0420 (3)0.50
C3S0.0420 (3)0.6956 (3)0.1455 (3)0.0413 (7)0.50
H3S10.06270.76970.08820.062*0.50
H3S20.01990.71450.23460.062*0.50
H3S30.12080.66240.17060.062*0.50
O1S0.00802 (10)0.61615 (9)0.07009 (12)0.0420 (3)0.50
C1S0.08424 (15)0.59087 (14)0.06422 (19)0.0517 (4)
H1SA0.10130.66630.12190.062*
H1SB0.16670.56310.04020.062*
C2S0.03436 (15)0.50368 (14)0.15193 (17)0.0483 (4)
H2SA0.04580.47430.18020.058*
H2SB0.09860.51910.24170.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0425 (6)0.0251 (5)0.0531 (6)0.0102 (4)0.0139 (5)0.0001 (4)
C10.0298 (6)0.0253 (6)0.0324 (7)0.0056 (5)0.0009 (5)0.0022 (5)
C20.0430 (8)0.0335 (7)0.0316 (7)0.0124 (5)0.0143 (6)0.0012 (5)
C30.0416 (7)0.0303 (6)0.0258 (7)0.0064 (5)0.0123 (5)0.0038 (5)
C40.0276 (6)0.0236 (6)0.0205 (6)0.0039 (4)0.0017 (4)0.0017 (4)
C50.0259 (6)0.0280 (6)0.0273 (6)0.0038 (5)0.0070 (5)0.0009 (5)
C60.0284 (6)0.0256 (6)0.0324 (7)0.0005 (5)0.0056 (5)0.0028 (5)
N10.0332 (6)0.0239 (5)0.0185 (5)0.0053 (4)0.0064 (4)0.0020 (4)
C70.0311 (6)0.0250 (6)0.0225 (6)0.0007 (5)0.0057 (5)0.0013 (4)
O20.0769 (8)0.0306 (5)0.0200 (5)0.0067 (4)0.0122 (5)0.0003 (3)
C80.0385 (7)0.0253 (6)0.0290 (7)0.0050 (5)0.0087 (5)0.0012 (5)
N1S0.0336 (6)0.0374 (6)0.0524 (7)0.0088 (4)0.0016 (5)0.0088 (5)
C3S0.0301 (14)0.0420 (16)0.0542 (18)0.0038 (11)0.0138 (13)0.0112 (13)
O1S0.0336 (6)0.0374 (6)0.0524 (7)0.0088 (4)0.0016 (5)0.0088 (5)
C1S0.0359 (8)0.0452 (9)0.0662 (11)0.0054 (6)0.0095 (7)0.0224 (8)
C2S0.0405 (8)0.0524 (9)0.0459 (9)0.0167 (7)0.0069 (7)0.0178 (7)
Geometric parameters (Å, º) top
O1—C11.3698 (14)C7—C81.5044 (16)
O1—H110.91 (2)C8—H8A0.9800
C1—C61.3837 (17)C8—H8B0.9800
C1—C21.3863 (18)C8—H8C0.9800
C2—C31.3843 (17)N1S—C3S1.301 (3)
C2—H20.9500N1S—C2S1.4568 (17)
C3—C41.3870 (16)N1S—C1S1.4643 (18)
C3—H30.9500C3S—H3S10.9800
C4—C51.3908 (16)C3S—H3S20.9800
C4—N11.4200 (14)C3S—H3S30.9800
C5—C61.3863 (16)C1S—C2Si1.487 (2)
C5—H50.9500C1S—H1SA0.9900
C6—H60.9500C1S—H1SB0.9900
N1—C71.3390 (14)C2S—C1Si1.487 (2)
N1—H10.880 (15)C2S—H2SA0.9900
C7—O21.2301 (14)C2S—H2SB0.9900
C1—O1—H11108.5 (11)O2—C7—C8121.74 (10)
O1—C1—C6117.83 (11)N1—C7—C8115.43 (10)
O1—C1—C2122.69 (11)C7—C8—H8A109.5
C6—C1—C2119.47 (11)C7—C8—H8B109.5
C3—C2—C1119.89 (11)H8A—C8—H8B109.5
C3—C2—H2120.1C7—C8—H8C109.5
C1—C2—H2120.1H8A—C8—H8C109.5
C2—C3—C4121.01 (11)H8B—C8—H8C109.5
C2—C3—H3119.5C3S—N1S—C2S109.99 (18)
C4—C3—H3119.5C3S—N1S—C1S108.89 (16)
C3—C4—C5118.85 (10)C2S—N1S—C1S108.66 (10)
C3—C4—N1118.20 (10)N1S—C1S—C2Si111.21 (12)
C5—C4—N1122.81 (10)N1S—C1S—H1SA109.4
C6—C5—C4120.18 (11)C2Si—C1S—H1SA109.4
C6—C5—H5119.9N1S—C1S—H1SB109.4
C4—C5—H5119.9C2Si—C1S—H1SB109.4
C1—C6—C5120.60 (11)H1SA—C1S—H1SB108.0
C1—C6—H6119.7N1S—C2S—C1Si110.88 (13)
C5—C6—H6119.7N1S—C2S—H2SA109.5
C7—N1—C4126.73 (10)C1Si—C2S—H2SA109.5
C7—N1—H1116.3 (9)N1S—C2S—H2SB109.5
C4—N1—H1116.9 (9)C1Si—C2S—H2SB109.5
O2—C7—N1122.83 (11)H2SA—C2S—H2SB108.1
Symmetry code: (i) x, y+1, z.
(ppip02) top
Crystal data top
2[C8H9NO2][C4H10N2]F(000) = 416
Mr = 388.46Dx = 1.320 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 15.893 (5) ÅCell parameters from 1227 reflections
b = 5.1664 (17) Åθ = 2.5–29°
c = 12.993 (4) ŵ = 0.09 mm1
β = 113.633 (5)°T = 150 K
V = 977.4 (6) Å3Plate, colourless
Z = 20.77 × 0.28 × 0.11 mm
Data collection top
Bruker Smart Apex CCD
diffractometer
2309 independent reflections
Radiation source: fine-focus sealed tube1778 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
ω and phi scansθmax = 28.6°, θmin = 1.4°
Absorption correction: multi-scan
SADABS
h = 1721
Tmin = 0.690, Tmax = 1k = 66
5628 measured reflectionsl = 1716
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.078Hydrogen site location: geom/difmap
wR(F2) = 0.165Riding/refall
S = 1.18 w = 1/[σ2(Fo2) + (0.052P)2 + 0.5663P]
where P = (Fo2 + 2Fc2)/3
2309 reflections(Δ/σ)max = 0.002
140 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.45 e Å3
Crystal data top
2[C8H9NO2][C4H10N2]V = 977.4 (6) Å3
Mr = 388.46Z = 2
Monoclinic, P21/cMo Kα radiation
a = 15.893 (5) ŵ = 0.09 mm1
b = 5.1664 (17) ÅT = 150 K
c = 12.993 (4) Å0.77 × 0.28 × 0.11 mm
β = 113.633 (5)°
Data collection top
Bruker Smart Apex CCD
diffractometer
2309 independent reflections
Absorption correction: multi-scan
SADABS
1778 reflections with I > 2σ(I)
Tmin = 0.690, Tmax = 1Rint = 0.046
5628 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0780 restraints
wR(F2) = 0.165Riding/refall
S = 1.18Δρmax = 0.34 e Å3
2309 reflectionsΔρmin = 0.45 e Å3
140 parameters
Special details top

Experimental. INTENSITY STATISTICS FOR DATASET # 1 PPIP02.hkl

Resolution #Data #Theory %Complete Redundancy Mean I Mean I/s R(int) R(sigma)

Inf - 2.20 129 129 100.0 2.96 408.9 33.95 0.0160 0.0126 2.20 - 1.70 129 129 100.0 3.26 185.2 21.91 0.0241 0.0248 1.70 - 1.45 149 149 100.0 3.30 87.5 14.22 0.0419 0.0432 1.45 - 1.30 141 141 100.0 3.11 49.6 9.74 0.0616 0.0623 1.30 - 1.20 148 148 100.0 2.72 66.1 10.40 0.0563 0.0683 1.20 - 1.10 202 202 100.0 2.71 56.0 8.66 0.0635 0.0729 1.10 - 1.00 262 263 99.6 2.43 50.2 7.56 0.0610 0.0872 1.00 - 0.95 209 209 100.0 2.25 25.5 5.39 0.1022 0.1364 0.95 - 0.90 227 227 100.0 2.16 24.0 5.11 0.1186 0.1467 0.90 - 0.85 275 277 99.3 2.03 19.8 4.32 0.1427 0.1767 0.85 - 0.80 351 360 97.5 1.83 17.6 4.09 0.1843 0.2106 0.80 - 0.75 321 462 69.5 1.12 17.7 3.84 0.1886 0.2388 0.75 - 0.74 14 65 21.5 0.22 15.0 2.36 0.3500 —————————————————————————— 0.85 - 0.74 686 887 77.3 1.34 17.6 3.94 0.1860 0.2263 Inf - 0.74 2557 2761 92.6 2.19 62.3 8.66 0.0462 0.0635

Merged [A], lowest resolution = 14.56 Angstroms, 81 outliers downweighted

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. TITL prpp02 in P2(1)/c CELL 0.71073 15.8932 5.1664 12.9927 90.000 113.633 90.000 ZERR 2.00 0.0052 0.0017 0.0043 0.000 0.005 0.000 L A T T 1 SYMM –X, 0.5+Y, 0.5-Z SFAC C H N O UNIT 40 56 8 8 TEMP -123

L.S. 4 BOND $H MPLA 6 C1 C2 C3 C4 C5 C6 MPLA 4 N1 C7 C8 O2 FMAP 2 PLAN 10 REM EXTI 0.000000 HTAB EQIV $1 X, Y+1, Z RTAB D1 H11 N1S RTAB D2 H1 O2_$1 RTAB D3 H1S O1_$1 ACTA WGHT 0.052000 0.566300 FVAR 0.59796 O1 4 0.341963 0.663432 0.029220 11.00000 0.02796 0.02019 = 0.02636 - 0.00319 0.02038 - 0.00378 H11 2 0.368816 0.820648 0.023291 11.00000 0.03161 C1 1 0.292695 0.681474 0.094458 11.00000 0.01725 0.01631 = 0.01461 0.00370 0.00723 0.00321 C2 1 0.304467 0.881126 0.170911 11.00000 0.01827 0.01466 = 0.01806 0.00052 0.00860 - 0.00121 AFIX 43 H2 2 0.347412 1.015212 0.178284 11.00000 - 1.20000 AFIX 0 C3 1 0.253548 0.885134 0.236646 11.00000 0.02015 0.01660 = 0.01370 - 0.00234 0.00656 0.00021 AFIX 43 H3 2 0.262093 1.022089 0.288678 11.00000 - 1.20000 AFIX 0 C4 1 0.190382 0.690847 0.226885 11.00000 0.01468 0.01790 = 0.01239 0.00408 0.00630 0.00426 C5 1 0.177462 0.491219 0.149061 11.00000 0.02111 0.01941 = 0.01573 - 0.00028 0.00892 - 0.00229 AFIX 43 H5 2 0.133824 0.358553 0.140772 11.00000 - 1.20000 AFIX 0 C6 1 0.228779 0.488069 0.083999 11.00000 0.02232 0.01706 = 0.01393 - 0.00267 0.00780 - 0.00012 AFIX 43 H6 2 0.220097 0.351850 0.031600 11.00000 - 1.20000 AFIX 0 N1 3 0.138357 0.706806 0.294468 11.00000 0.02334 0.01667 = 0.01709 - 0.00139 0.01304 0.00184 H1 2 0.132223 0.864773 0.315343 11.00000 0.03096 C7 1 0.109984 0.502214 0.337904 11.00000 0.01596 0.02173 = 0.01322 0.00104 0.00570 0.00222 O2 4 0.124109 0.276462 0.320634 11.00000 0.04856 0.01842 = 0.02543 0.00242 0.02654 0.00191 C8 1 0.059985 0.571561 0.411112 11.00000 0.02478 0.02873 = 0.01920 - 0.00204 0.01401 - 0.00204 AFIX 137 H8A 2 0.004592 0.464949 0.390156 11.00000 - 1.50000 H8B 2 0.042677 0.754810 0.400780 11.00000 - 1.50000 H8C 2 0.100170 0.540025 0.490012 11.00000 - 1.50000 AFIX 0 N1S 3 0.418954 1.114096 0.002035 11.00000 0.01817 0.01583 = 0.02253 - 0.00077 0.01133 0.00152 H1S 2 0.383232 1.253444 - 0.002831 11.00000 0.02001 C1S 1 0.430115 1.080910 - 0.105223 11.00000 0.02004 0.01810 = 0.01814 0.00205 0.00810 - 0.00169 AFIX 23 H1S1 2 0.458565 1.237706 - 0.121309 11.00000 - 1.20000 H1S2 2 0.369349 1.055363 - 0.167663 11.00000 - 1.20000 AFIX 0 C2S 1 0.509404 1.152325 0.095455 11.00000 0.02324 0.01594 = 0.01881 - 0.00260 0.01125 - 0.00414 AFIX 23 H2S1 2 0.501402 1.176602 0.166580 11.00000 - 1.20000 H2S2 2 0.538941 1.309628 0.081694 11.00000 - 1.20000

HKLF 4 1 0 0 1 0 - 1 0 1 0 0

REM prpp02 in P2(1)/c REM R1 = 0.0779 for 1778 Fo > 4sig(Fo) and 0.1031 for all 2309 data REM 140 parameters refined using 0 restraints

END

WGHT 0.0512 0.5796 REM Highest difference peak 0.336, deepest hole -0.447, 1-σ level 0.065 Q1 1 0.2357 0.6650 0.0640 11.00000 0.05 0.34 Q2 1 0.2479 0.7336 0.2619 11.00000 0.05 0.32 Q3 1 0.1727 0.2456 0.3008 11.00000 0.05 0.29 Q4 1 0.1991 0.8574 0.2052 11.00000 0.05 0.29 Q5 1 0.0765 0.5520 0.3670 11.00000 0.05 0.28 Q6 1 0.1539 0.6050 0.3405 11.00000 0.05 0.28 Q7 1 0.5306 1.0133 0.1064 11.00000 0.05 0.28 Q8 1 0.0751 0.3628 0.2972 11.00000 0.05 0.28 Q9 1 0.2856 0.8074 0.1184 11.00000 0.05 0.27 Q10 1 0.4719 1.1280 0.0427 11.00000 0.05 0.25

#=============================================================================== # PLATON/CHECK-(191101) versus check.def version of 16/11/01 for entry: ppip02 # Data From: ppip02.cif - Data Type: CIF Bond Precision C—C = 0.0039 A # # CELL 0.71073 15.893 5.166 12.993 90.00 113.63 90.00 977.40 # SpaceGroup from Symmetry P21/c Hall: –P 2ybc # Reported P21/c ? # MoietyFormula C8 H9 N O2, 0.5(C4 H10 N2) # Reported ? # SumFormula C10 H14 N2 O2 # Reported C20 H28 N4 O4 # Mr = 194.23[Calc], 388.46[Rep] # Dx,gcm-3 = 1.320[Calc], 1.320[Rep] # Z = 4[Calc], 2[Rep] # Mu (mm-1) = 0.093[Calc], 0.093[Rep] # F000 = 416.0[Calc], 416.0[Rep] # Reported T limits: Tmin=0.690 Tmax=1.000 'MULTISCAN' # Calculated T limits: Tmin=0.969 Tmin'=0.931 Tmax=0.990 # Reported Hmax= 21, Kmax= 6, Lmax= 17, Nref= 2309, Th(max)= 28.55 # Calculated Hmax= 21, Kmax= 6, Lmax= 17, Nref= 2487 (2487), Ratio= 0.93 (0.93) # R= 0.0779 (1778), wR2= 0.1652 (2309), S = 1.179, Npar= 140 #=============================================================================== >>> The Following ALERTS were generated <<<

061_ALERT B Tmax/Tmin Range Test RR' too large ·········.. 0.73

SADABS corrects for all systematic errors, not just crystal absorption. Extra absorption may come from glue, glass fibre etc. It can also be affected by crystal quality, which in this case is rather low.

#=============================================================================== 041_ALERT C Calc. and Rep. SumFormula Strings Differ.. ? 045_ALERT C Calculated and Reported Z differ by ·········. 2.00 Ratio

Z=2 description of formula chosen to be consistenet with other structures reported here.

062_ALERT C Rescale T(min) & T(max) by ··················. 0.99

No action taken

063_ALERT C Crystal Probably too Large for Beam Size ···.. 0.77 mm

Gorbitz has shown that use of a large crystal does not appear to matter. See C. H. Gorbitz Acta Cryst. (1999). B55, 1090–1098

125_ALERT C No _symmetry_space_group_name_Hall given ···.. ?

-P 2ybc

ALERT Level Summary 1 ALERT Level B = Potentially Serious Problem 6 ALERT Level C = Check & Explain

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.34196 (12)0.6634 (4)0.02922 (15)0.0218 (4)
H110.369 (2)0.821 (7)0.023 (2)0.032 (9)*
C10.29270 (16)0.6815 (5)0.09446 (19)0.0158 (5)
C20.30447 (16)0.8811 (5)0.1709 (2)0.0166 (5)
H20.34741.01520.17830.020*
C30.25355 (16)0.8851 (5)0.23665 (19)0.0169 (5)
H30.26211.02210.28870.020*
C40.19038 (16)0.6908 (5)0.22688 (19)0.0147 (5)
C50.17746 (17)0.4912 (5)0.14906 (19)0.0183 (5)
H50.13380.35860.14080.022*
C60.22878 (17)0.4881 (5)0.08400 (19)0.0176 (5)
H60.22010.35190.03160.021*
N10.13836 (15)0.7068 (4)0.29447 (17)0.0175 (5)
H10.132 (2)0.865 (6)0.315 (3)0.031 (9)*
C70.10998 (16)0.5022 (5)0.33790 (19)0.0170 (5)
O20.12411 (14)0.2765 (4)0.32063 (15)0.0271 (5)
C80.05999 (18)0.5716 (6)0.4111 (2)0.0226 (6)
H8A0.00460.46490.39020.034*
H8B0.04270.75480.40080.034*
H8C0.10020.54000.49000.034*
N1S0.41895 (14)1.1141 (4)0.00203 (18)0.0178 (5)
H1S0.3832 (19)1.253 (6)0.003 (2)0.020 (7)*
C1S0.43012 (17)1.0809 (5)0.1052 (2)0.0186 (6)
H1S10.45861.23770.12130.022*
H1S20.36931.05540.16770.022*
C2S0.50940 (17)1.1523 (5)0.0955 (2)0.0184 (6)
H2S10.50141.17660.16660.022*
H2S20.53891.30960.08170.022*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0280 (10)0.0202 (11)0.0264 (10)0.0038 (8)0.0204 (8)0.0032 (8)
C10.0173 (12)0.0163 (13)0.0146 (11)0.0032 (10)0.0072 (9)0.0037 (10)
C20.0183 (12)0.0147 (13)0.0181 (12)0.0012 (10)0.0086 (10)0.0005 (10)
C30.0202 (12)0.0166 (13)0.0137 (11)0.0002 (11)0.0066 (10)0.0023 (10)
C40.0147 (11)0.0179 (13)0.0124 (11)0.0043 (10)0.0063 (9)0.0041 (10)
C50.0211 (12)0.0194 (13)0.0157 (11)0.0023 (11)0.0089 (10)0.0003 (11)
C60.0223 (13)0.0171 (14)0.0139 (11)0.0001 (11)0.0078 (10)0.0027 (10)
N10.0233 (11)0.0167 (12)0.0171 (10)0.0018 (10)0.0130 (9)0.0014 (9)
C70.0160 (12)0.0217 (14)0.0132 (11)0.0022 (11)0.0057 (9)0.0010 (10)
O20.0486 (13)0.0184 (11)0.0254 (10)0.0019 (9)0.0265 (9)0.0024 (9)
C80.0248 (13)0.0287 (16)0.0192 (12)0.0020 (12)0.0140 (11)0.0020 (11)
N1S0.0182 (11)0.0158 (11)0.0225 (11)0.0015 (9)0.0113 (9)0.0008 (9)
C1S0.0200 (12)0.0181 (14)0.0181 (12)0.0017 (10)0.0081 (10)0.0021 (10)
C2S0.0232 (13)0.0159 (14)0.0188 (12)0.0041 (11)0.0112 (10)0.0026 (10)
Geometric parameters (Å, º) top
O1—C11.368 (3)C7—O21.225 (3)
O1—H110.93 (3)C7—C81.507 (3)
C1—C21.392 (3)C8—H8A0.9800
C1—C61.392 (3)C8—H8B0.9800
C2—C31.392 (3)C8—H8C0.9800
C2—H20.9500N1S—C2S1.476 (3)
C3—C41.389 (3)N1S—C1S1.484 (3)
C3—H30.9500N1S—H1S0.90 (3)
C4—C51.401 (3)C1S—C2Si1.515 (4)
C4—N11.430 (3)C1S—H1S10.9900
C5—C61.390 (3)C1S—H1S20.9900
C5—H50.9500C2S—C1Si1.515 (4)
C6—H60.9500C2S—H2S10.9900
N1—C71.358 (3)C2S—H2S20.9900
N1—H10.88 (3)
C1—O1—H11112.7 (18)O2—C7—C8121.6 (2)
O1—C1—C2123.1 (2)N1—C7—C8115.1 (2)
O1—C1—C6117.8 (2)C7—C8—H8A109.5
C2—C1—C6119.1 (2)C7—C8—H8B109.5
C1—C2—C3120.3 (2)H8A—C8—H8B109.5
C1—C2—H2119.9C7—C8—H8C109.5
C3—C2—H2119.9H8A—C8—H8C109.5
C4—C3—C2120.6 (2)H8B—C8—H8C109.5
C4—C3—H3119.7C2S—N1S—C1S110.12 (19)
C2—C3—H3119.7C2S—N1S—H1S109.2 (18)
C3—C4—C5119.3 (2)C1S—N1S—H1S109.6 (18)
C3—C4—N1118.5 (2)N1S—C1S—C2Si108.9 (2)
C5—C4—N1122.2 (2)N1S—C1S—H1S1109.9
C6—C5—C4119.7 (2)C2Si—C1S—H1S1109.9
C6—C5—H5120.1N1S—C1S—H1S2109.9
C4—C5—H5120.1C2Si—C1S—H1S2109.9
C5—C6—C1121.0 (2)H1S1—C1S—H1S2108.3
C5—C6—H6119.5N1S—C2S—C1Si109.8 (2)
C1—C6—H6119.5N1S—C2S—H2S1109.7
C7—N1—C4125.5 (2)C1Si—C2S—H2S1109.7
C7—N1—H1120 (2)N1S—C2S—H2S2109.7
C4—N1—H1114 (2)C1Si—C2S—H2S2109.7
O2—C7—N1123.3 (2)H2S1—C2S—H2S2108.2
Symmetry code: (i) x+1, y+2, z.
(pardip) top
Crystal data top
[C8H9NO2][C10H8N2]F(000) = 1296
Mr = 307.35Dx = 1.306 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.2906 (10) ÅCell parameters from 5375 reflections
b = 24.103 (2) Åθ = 2–28.5°
c = 11.5526 (10) ŵ = 0.09 mm1
β = 96.1484 (16)°T = 150 K
V = 3125.8 (5) Å3Block, colourless
Z = 80.46 × 0.28 × 0.18 mm
Data collection top
Bruker SMART APEX CCD
diffractometer
7766 independent reflections
Radiation source: fine-focus sealed tube6044 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
ω and phi scansθmax = 29.2°, θmin = 1.7°
Absorption correction: multi-scan
SADABS
h = 1414
Tmin = 0.830, Tmax = 1k = 1931
20270 measured reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: geom/difmap
wR(F2) = 0.128Riding/refall
S = 1.04 w = 1/[σ2(Fo2) + (0.0676P)2 + 0.569P]
where P = (Fo2 + 2Fc2)/3
7766 reflections(Δ/σ)max = 0.001
433 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
[C8H9NO2][C10H8N2]V = 3125.8 (5) Å3
Mr = 307.35Z = 8
Monoclinic, P21/cMo Kα radiation
a = 11.2906 (10) ŵ = 0.09 mm1
b = 24.103 (2) ÅT = 150 K
c = 11.5526 (10) Å0.46 × 0.28 × 0.18 mm
β = 96.1484 (16)°
Data collection top
Bruker SMART APEX CCD
diffractometer
7766 independent reflections
Absorption correction: multi-scan
SADABS
6044 reflections with I > 2σ(I)
Tmin = 0.830, Tmax = 1Rint = 0.022
20270 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.128Riding/refall
S = 1.04Δρmax = 0.36 e Å3
7766 reflectionsΔρmin = 0.25 e Å3
433 parameters
Special details top

Experimental. INTENSITY STATISTICS FOR DATASET # 1 pardip.hkl

Resolution #Data #Theory %Complete Redundancy Mean I Mean I/s R(int) R(sigma)

Inf - 2.05 407 410 99.3 3.74 464.5 41.27 0.0103 0.0178 2.05 - 1.60 437 437 100.0 3.86 160.0 36.63 0.0144 0.0191 1.60 - 1.40 403 403 100.0 3.66 64.3 28.06 0.0267 0.0235 1.40 - 1.25 504 504 100.0 3.31 56.9 24.36 0.0317 0.0272 1.25 - 1.15 474 474 100.0 3.03 63.0 22.29 0.0303 0.0279 1.15 - 1.05 700 700 100.0 2.84 58.8 21.09 0.0300 0.0304 1.05 - 1.00 466 466 100.0 2.66 31.8 15.12 0.0386 0.0419 1.00 - 0.95 527 527 100.0 2.54 25.1 13.58 0.0488 0.0511 0.95 - 0.90 702 703 99.9 2.38 20.9 11.51 0.0579 0.0617 0.90 - 0.85 868 868 100.0 2.22 16.4 8.83 0.0659 0.0797 0.85 - 0.80 1054 1074 98.1 2.05 11.7 6.52 0.0906 0.1150 0.80 - 0.75 1220 1394 87.5 1.61 10.7 5.08 0.1020 0.1471 0.75 - 0.73 195 706 27.6 0.30 8.8 3.54 0.1285 0.2392 —————————————————————————— 0.85 - 0.73 2469 3174 77.8 1.47 11.0 5.57 0.0959 0.1383 Inf - 0.73 7957 8666 91.8 2.38 58.9 15.76 0.0221 0.0326

Merged [A], lowest resolution = 12.05 Angstroms, 326 outliers downweighted

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. TITL pardip in P2(1)/c CELL 0.71073 11.2906 24.1029 11.5526 90.0000 96.1484 90.0000 ZERR 8.00 0.0010 0.0021 0.0010 0.0000 0.0016 0.0000 L A T T 1 SYMM –X, 0.5+Y, 0.5-Z SFAC C H N O UNIT 144 136 24 16 TEMP -123

L.S. 4 BOND $H

FMAP 2 PLAN 10 ACTA REM EXTI 0.000000 HTAB EQIV $1 x - 1, y, z - 1 EQIV $2 - x, y - 1/2, -z + 1/2 RTAB D1 H11A O2B RTAB D2 H1A N10S RTAB D3 H11B O2A_$1 RTAB D4 H1B N1T_$2 MPLA 6 C1A C2A C3A C4A C5A C6A MPLA 4 N1A C7A O2A C8A MPLA 6 C1B C2B C3B C4B C5B C6B MPLA 4 N1B C7B O2B C8B MPLA 6 N1S C2S C3S C4S C5S C6S MPLA 6 C7S C8S C9S N10S C11S C12S MPLA 6 N1T C2T C3T C4T C5T C6T MPLA 6 C7T C8T C9T N10T C11T C12T

WGHT 0.067600 0.569000 FVAR 0.38390 O1A 4 0.468341 0.542049 0.678691 11.00000 0.02960 0.03000 = 0.03589 - 0.00933 - 0.00906 0.00483 H11A 2 0.398824 0.546984 0.632763 11.00000 0.05332 C1A 1 0.490347 0.587408 0.747280 11.00000 0.02208 0.02536 = 0.02432 - 0.00111 - 0.00028 - 0.00021 C2A 1 0.418166 0.634555 0.740458 11.00000 0.01982 0.02980 = 0.02391 0.00182 - 0.00278 0.00291 AFIX 43 H2A 2 0.349507 0.636108 0.685305 11.00000 - 1.20000 AFIX 0 C3A 1 0.446463 0.678953 0.813812 11.00000 0.02127 0.02461 = 0.02550 0.00347 0.00079 0.00556 AFIX 43 H3A 2 0.397019 0.710939 0.807990 11.00000 - 1.20000 AFIX 0 C4A 1 0.546273 0.677787 0.896368 11.00000 0.02099 0.02179 = 0.02117 0.00233 0.00162 0.00100 C5A 1 0.617406 0.630375 0.903904 11.00000 0.01860 0.02538 = 0.02536 0.00306 - 0.00392 0.00199 AFIX 43 H5A 2 0.685076 0.628393 0.960195 11.00000 - 1.20000 AFIX 0 C6A 1 0.589547 0.586258 0.829548 11.00000 0.02182 0.02338 = 0.02952 0.00023 - 0.00152 0.00469 AFIX 43 H6A 2 0.639382 0.554402 0.834803 11.00000 - 1.20000 AFIX 0 N1A 3 0.570755 0.726340 0.964198 11.00000 0.02534 0.02168 = 0.02514 0.00156 - 0.00214 0.00490 H1A 2 0.528600 0.755496 0.938074 11.00000 0.04077 C7A 1 0.652876 0.733440 1.056366 11.00000 0.02513 0.02670 = 0.02488 - 0.00010 0.00056 0.00169 O2A 4 0.715199 0.695403 1.101200 11.00000 0.03566 0.03127 = 0.03330 - 0.00283 - 0.01238 0.00797 C8A 1 0.666515 0.791851 1.101655 11.00000 0.04008 0.02883 = 0.03497 - 0.00632 - 0.00322 0.00235 AFIX 137 H8A3 2 0.598934 0.814290 1.068278 11.00000 - 1.50000 H8A1 2 0.740749 0.807731 1.079507 11.00000 - 1.50000 H8A2 2 0.668749 0.791588 1.186689 11.00000 - 1.50000 AFIX 0 O1B 4 - 0.174036 0.704721 0.318695 11.00000 0.03911 0.02578 = 0.03114 - 0.00378 - 0.00914 0.00647 H11B 2 - 0.211974 0.700932 0.248192 11.00000 0.05358 C1B 1 - 0.106676 0.658066 0.342991 11.00000 0.02533 0.02259 = 0.02321 0.00088 0.00006 0.00038 C2B 1 - 0.119352 0.610414 0.275292 11.00000 0.02431 0.02591 = 0.02152 - 0.00167 - 0.00317 - 0.00260 AFIX 43 H2B 2 - 0.177905 0.608894 0.209876 11.00000 - 1.20000 AFIX 0 C3B 1 - 0.046446 0.565088 0.303324 11.00000 0.02535 0.02205 = 0.02183 - 0.00358 0.00020 - 0.00356 AFIX 43 H3B 2 - 0.055548 0.532637 0.256544 11.00000 - 1.20000 AFIX 0 C4B 1 0.039987 0.566232 0.398883 11.00000 0.02265 0.02174 = 0.02015 0.00108 0.00208 - 0.00208 C5B 1 0.050887 0.613713 0.467568 11.00000 0.02761 0.02768 = 0.01930 - 0.00119 - 0.00301 - 0.00202 AFIX 43 H5B 2 0.108449 0.615049 0.533808 11.00000 - 1.20000 AFIX 0 C6B 1 - 0.021950 0.659059 0.439667 11.00000 0.03405 0.02363 = 0.02169 - 0.00448 - 0.00274 - 0.00137 AFIX 43 H6B 2 - 0.013929 0.691283 0.487214 11.00000 - 1.20000 AFIX 0 N1B 3 0.112068 0.517925 0.419488 11.00000 0.02407 0.02234 = 0.02288 - 0.00190 - 0.00251 - 0.00047 H1B 2 0.087923 0.487090 0.376333 11.00000 0.04029 C7B 1 0.214696 0.512872 0.489469 11.00000 0.02482 0.03001 = 0.02146 - 0.00096 0.00127 0.00014 O2B 4 0.258755 0.551080 0.551226 11.00000 0.03111 0.03778 = 0.03670 - 0.01212 - 0.01132 0.00473 C8B 1 0.274380 0.457036 0.487158 11.00000 0.03165 0.03226 = 0.03280 - 0.00160 - 0.00364 0.00592 AFIX 137 H8B3 2 0.339124 0.458875 0.437160 11.00000 - 1.50000 H8B2 2 0.215995 0.429191 0.456506 11.00000 - 1.50000 H8B1 2 0.306844 0.446724 0.566306 11.00000 - 1.50000 AFIX 0 N1S 3 0.222276 1.019976 0.435280 11.00000 0.03977 0.02698 = 0.03044 0.00382 - 0.00965 - 0.00428 C2S 1 0.322755 0.991616 0.427341 11.00000 0.03867 0.03236 = 0.02666 0.00453 0.00101 - 0.00830 AFIX 43 H2S 2 0.365539 0.998657 0.362407 11.00000 - 1.20000 AFIX 0 C3S 1 0.368266 0.952569 0.508117 11.00000 0.02699 0.02836 = 0.03037 0.00210 0.00265 - 0.00093 AFIX 43 H3S 2 0.440243 0.933651 0.497969 11.00000 - 1.20000 AFIX 0 C4S 1 0.307916 0.941266 0.604075 11.00000 0.02393 0.01942 = 0.02556 - 0.00001 - 0.00101 - 0.00263 C5S 1 0.202213 0.970003 0.612075 11.00000 0.02388 0.02509 = 0.02803 0.00008 0.00005 - 0.00208 AFIX 43 H5S 2 0.156619 0.963346 0.675174 11.00000 - 1.20000 AFIX 0 C6S 1 0.164241 1.008455 0.526880 11.00000 0.02753 0.02448 = 0.03547 - 0.00073 - 0.00850 0.00043 AFIX 43 H6S 2 0.092186 1.027845 0.534284 11.00000 - 1.20000 AFIX 0 C7S 1 0.354988 0.900802 0.694628 11.00000 0.02735 0.02000 = 0.02559 - 0.00019 0.00010 0.00116 C8S 1 0.474619 0.885461 0.708703 11.00000 0.02819 0.04325 = 0.04513 0.01464 0.00658 0.00446 AFIX 43 H9S 2 0.528870 0.900876 0.660077 11.00000 - 1.20000 H8S 2 0.595149 0.837721 0.801453 11.00000 - 1.20000 AFIX 0 C9S 1 0.513411 0.847636 0.794045 11.00000 0.03272 0.04401 = 0.05064 0.01325 - 0.00025 0.01203 N10S 3 0.443577 0.824310 0.866156 11.00000 0.04475 0.02682 = 0.03524 0.00472 - 0.00069 0.00767 C11S 1 0.329057 0.839402 0.852425 11.00000 0.04391 0.02964 = 0.03444 0.00830 0.00891 0.00501 AFIX 43 H12S 2 0.277106 0.823606 0.902913 11.00000 - 1.20000 H11S 2 0.199687 0.885372 0.763335 11.00000 - 1.20000 AFIX 0 C12S 1 0.281958 0.876579 0.769203 11.00000 0.03153 0.02837 = 0.03199 0.00478 0.00651 0.00523 N1T 3 - 0.035898 0.919339 0.231623 11.00000 0.03172 0.02330 = 0.02423 0.00072 - 0.00005 0.00234 C2T 1 0.080328 0.915385 0.268242 11.00000 0.03095 0.02354 = 0.02498 0.00089 0.00358 - 0.00175 AFIX 43 H2T 2 0.134144 0.938443 0.232483 11.00000 - 1.20000 AFIX 0 C3T 1 0.126373 0.879685 0.355045 11.00000 0.02423 0.02476 = 0.02559 - 0.00059 - 0.00021 - 0.00053 AFIX 43 H3T 2 0.209760 0.878535 0.377594 11.00000 - 1.20000 AFIX 0 C4T 1 0.050087 0.845407 0.409326 11.00000 0.02663 0.01782 = 0.02068 - 0.00246 0.00163 0.00251 C5T 1 - 0.070672 0.848133 0.369596 11.00000 0.02538 0.02302 = 0.02996 0.00213 0.00393 - 0.00044 AFIX 43 H5T 2 - 0.126340 0.824897 0.402320 11.00000 - 1.20000 AFIX 0 C6T 1 - 0.108347 0.885098 0.281941 11.00000 0.02472 0.02755 = 0.03087 0.00052 - 0.00170 0.00168 AFIX 43 H6T 2 - 0.190979 0.886285 0.255709 11.00000 - 1.20000 AFIX 0 C7T 1 0.097446 0.807945 0.505079 11.00000 0.02857 0.01735 = 0.02176 - 0.00155 0.00029 0.00104 C8T 1 0.210759 0.785063 0.507307 11.00000 0.03136 0.03067 = 0.02615 0.00334 0.00600 0.00707 AFIX 43 H8T 2 0.258795 0.792786 0.446580 11.00000 - 1.20000 AFIX 0 C9T 1 0.252756 0.750935 0.598910 11.00000 0.03401 0.03281 = 0.03120 0.00266 0.00178 0.01106 AFIX 43 H9T 2 0.330401 0.735775 0.598699 11.00000 - 1.20000 AFIX 0 N10T 3 0.191354 0.737941 0.687452 11.00000 0.04026 0.03001 = 0.02800 0.00422 0.00077 0.00617 C12T 1 0.032213 0.794568 0.596571 11.00000 0.02839 0.02382 = 0.02684 - 0.00004 0.00392 0.00269 AFIX 43 H12T 2 - 0.045791 0.808998 0.598924 11.00000 - 1.20000 AFIX 0 C11T 1 0.082142 0.759963 0.684316 11.00000 0.03839 0.02951 = 0.02526 0.00317 0.00591 0.00066 AFIX 43 H11T 2 0.036083 0.751315 0.746080 11.00000 - 1.20000

HKLF 4

REM pardip in P2(1)/c REM R1 = 0.0471 for 6044 Fo > 4sig(Fo) and 0.0630 for all 7766 data REM 433 parameters refined using 0 restraints

END

WGHT 0.0675 0.5718 REM Highest difference peak 0.357, deepest hole -0.246, 1-σ level 0.048 Q1 1 0.4571 0.6117 0.7416 11.00000 0.05 0.36 Q2 1 0.5267 0.5843 0.8033 11.00000 0.05 0.33 Q3 1 0.0705 0.8256 0.4569 11.00000 0.05 0.32 Q4 1 0.4214 0.8990 0.7200 11.00000 0.05 0.30 Q5 1 0.0541 0.5936 0.4228 11.00000 0.05 0.30 Q6 1 0.0933 0.8984 0.3190 11.00000 0.05 0.30 Q7 1 0.0575 0.7957 0.5414 11.00000 0.05 0.29 Q8 1 0.4869 0.6762 0.8623 11.00000 0.05 0.29 Q9 1 - 0.0113 0.5647 0.3659 11.00000 0.05 0.29 Q10 1 0.3373 0.9763 0.4791 11.00000 0.05 0.29

#=============================================================================== # PLATON/CHECK-(191101) versus check.def version of 16/11/01 for entry: pardip # Data From: pardip.cif - Data Type: CIF Bond Precision C—C = 0.0019 A # # CELL 0.71073 11.291 24.103 11.553 90.00 96.15 90.00 3125.80 # SpaceGroup from Symmetry P21/c Hall: –P 2ybc # Reported P21/c ? # MoietyFormula C8 H9 N O2, C10 H8 N2 # Reported [C8H9NO2][C10H8N2] # SumFormula C18 H17 N3 O2 # Reported C18 H17 N3 O2 # Mr = 307.35[Calc], 307.35[Rep] # Dx,gcm-3 = 1.306[Calc], 1.306[Rep] # Z = 8[Calc], 8[Rep] # Mu (mm-1) = 0.087[Calc], 0.087[Rep] # F000 = 1296.0[Calc], 1296.0[Rep] # Reported T limits: Tmin=0.830 Tmax=1.000 'MULTISCAN' # Calculated T limits: Tmin=0.971 Tmin'=0.961 Tmax=0.984 # Reported Hmax= 14, Kmax= 31, Lmax= 15, Nref= 7766, Th(max)= 29.18 # Calculated Hmax= 15, Kmax= 33, Lmax= 15, Nref= 8454 (8454), Ratio= 0.92 (0.92) # R= 0.0471 (6044), wR2= 0.1280 (7766), S = 1.038, Npar= 433 #=============================================================================== >>> The Following ALERTS were generated <<<

042_ALERT C Calc. and Rep. MoietyFormula Strings Differ.. ?

No they don't.

061_ALERT C Tmax/Tmin Range Test RR' too large ·········.. 0.85 062_ALERT C Rescale T(min) & T(max) by ··················. 0.98

SADABS corrects for all systematic errors, not just crystal absorption. Extra absorption may come from glue, glass fibre etc.

125_ALERT C No _symmetry_space_group_name_Hall given ···.. ?

-P 2ybc

145_ALERT C su on beta Small or Missing (x 10000) ··· 16 Deg.

This is value produced by the Saint integration software. I think cell parameter s.u.s often seem unrealistically small with area detector data.

ALERT Level Summary 5 ALERT Level C = Check & Explain

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1A0.46834 (9)0.54205 (4)0.67869 (9)0.0327 (2)
H11A0.3988 (17)0.5470 (8)0.6328 (16)0.053 (5)*
C1A0.49035 (11)0.58741 (5)0.74728 (11)0.0241 (3)
C2A0.41817 (11)0.63456 (6)0.74046 (11)0.0249 (3)
H2A0.34950.63610.68530.030*
C3A0.44646 (11)0.67895 (6)0.81381 (11)0.0239 (3)
H3A0.39700.71090.80800.029*
C4A0.54627 (10)0.67779 (5)0.89637 (10)0.0214 (3)
C5A0.61741 (10)0.63037 (5)0.90390 (11)0.0236 (3)
H5A0.68510.62840.96020.028*
C6A0.58955 (11)0.58626 (5)0.82955 (11)0.0252 (3)
H6A0.63940.55440.83480.030*
N1A0.57076 (9)0.72634 (5)0.96420 (9)0.0244 (2)
H1A0.5286 (15)0.7555 (8)0.9381 (15)0.041 (5)*
C7A0.65288 (11)0.73344 (6)1.05637 (11)0.0257 (3)
O2A0.71520 (9)0.69540 (4)1.10120 (9)0.0346 (2)
C8A0.66652 (14)0.79185 (6)1.10166 (13)0.0351 (3)
H8A30.59890.81431.06830.053*
H8A10.74070.80771.07950.053*
H8A20.66870.79161.18670.053*
O1B0.17404 (9)0.70472 (4)0.31870 (9)0.0329 (2)
H11B0.2120 (17)0.7009 (8)0.2482 (17)0.054 (5)*
C1B0.10668 (11)0.65807 (5)0.34299 (11)0.0239 (3)
C2B0.11935 (11)0.61041 (5)0.27529 (11)0.0243 (3)
H2B0.17790.60890.20990.029*
C3B0.04645 (11)0.56509 (5)0.30332 (11)0.0232 (3)
H3B0.05550.53260.25650.028*
C4B0.03999 (11)0.56623 (5)0.39888 (10)0.0215 (3)
C5B0.05089 (11)0.61371 (6)0.46757 (11)0.0253 (3)
H5B0.10840.61500.53380.030*
C6B0.02195 (12)0.65906 (6)0.43967 (11)0.0269 (3)
H6B0.01390.69130.48720.032*
N1B0.11207 (9)0.51792 (5)0.41949 (9)0.0235 (2)
H1B0.0879 (15)0.4871 (7)0.3763 (15)0.040 (5)*
C7B0.21470 (11)0.51287 (6)0.48947 (11)0.0255 (3)
O2B0.25876 (9)0.55108 (4)0.55123 (9)0.0363 (3)
C8B0.27438 (13)0.45704 (6)0.48716 (13)0.0327 (3)
H8B30.33910.45890.43720.049*
H8B20.21600.42920.45650.049*
H8B10.30680.44670.56630.049*
N1S0.22228 (11)1.01998 (5)0.43528 (10)0.0334 (3)
C2S0.32276 (13)0.99162 (6)0.42734 (12)0.0327 (3)
H2S0.36550.99870.36240.039*
C3S0.36827 (12)0.95257 (6)0.50812 (12)0.0286 (3)
H3S0.44020.93370.49800.034*
C4S0.30792 (11)0.94127 (5)0.60407 (11)0.0232 (3)
C5S0.20221 (11)0.97000 (6)0.61208 (12)0.0259 (3)
H5S0.15660.96330.67520.031*
C6S0.16424 (12)1.00846 (6)0.52688 (12)0.0300 (3)
H6S0.09221.02780.53430.036*
C7S0.35499 (11)0.90080 (5)0.69463 (11)0.0245 (3)
C8S0.47462 (13)0.88546 (7)0.70870 (14)0.0387 (4)
H9S0.52890.90090.66010.046*
H8S0.59510.83770.80150.046*
C9S0.51341 (14)0.84764 (7)0.79405 (15)0.0428 (4)
N10S0.44358 (11)0.82431 (5)0.86616 (11)0.0360 (3)
C11S0.32906 (14)0.83940 (6)0.85242 (13)0.0357 (3)
H12S0.27710.82360.90290.043*
H11S0.19970.88540.76330.043*
C12S0.28196 (12)0.87658 (6)0.76920 (12)0.0304 (3)
N1T0.03590 (10)0.91934 (5)0.23162 (9)0.0266 (2)
C2T0.08033 (12)0.91539 (6)0.26824 (11)0.0264 (3)
H2T0.13410.93840.23250.032*
C3T0.12637 (11)0.87968 (5)0.35504 (11)0.0251 (3)
H3T0.20980.87850.37760.030*
C4T0.05009 (11)0.84541 (5)0.40933 (11)0.0218 (3)
C5T0.07067 (11)0.84813 (6)0.36960 (12)0.0261 (3)
H5T0.12630.82490.40230.031*
C6T0.10835 (12)0.88510 (6)0.28194 (12)0.0281 (3)
H6T0.19100.88630.25570.034*
C7T0.09745 (11)0.80794 (5)0.50508 (11)0.0227 (3)
C8T0.21076 (12)0.78506 (6)0.50731 (12)0.0292 (3)
H8T0.25880.79280.44660.035*
C9T0.25276 (13)0.75094 (6)0.59891 (12)0.0328 (3)
H9T0.33040.73580.59870.039*
N10T0.19135 (11)0.73794 (5)0.68745 (10)0.0330 (3)
C12T0.03221 (12)0.79457 (5)0.59657 (11)0.0263 (3)
H12T0.04580.80900.59890.032*
C11T0.08214 (13)0.75996 (6)0.68432 (12)0.0309 (3)
H11T0.03610.75130.74610.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0296 (5)0.0300 (5)0.0359 (5)0.0048 (4)0.0091 (4)0.0093 (4)
C1A0.0221 (6)0.0254 (7)0.0243 (6)0.0002 (5)0.0003 (5)0.0011 (5)
C2A0.0198 (6)0.0298 (7)0.0239 (6)0.0029 (5)0.0028 (5)0.0018 (5)
C3A0.0213 (6)0.0246 (6)0.0255 (6)0.0056 (5)0.0008 (5)0.0035 (5)
C4A0.0210 (6)0.0218 (6)0.0212 (6)0.0010 (5)0.0016 (4)0.0023 (5)
C5A0.0186 (5)0.0254 (6)0.0254 (6)0.0020 (5)0.0039 (5)0.0031 (5)
C6A0.0218 (6)0.0234 (6)0.0295 (7)0.0047 (5)0.0015 (5)0.0002 (5)
N1A0.0253 (5)0.0217 (5)0.0251 (5)0.0049 (4)0.0021 (4)0.0016 (4)
C7A0.0251 (6)0.0267 (7)0.0249 (6)0.0017 (5)0.0006 (5)0.0001 (5)
O2A0.0357 (5)0.0313 (5)0.0333 (5)0.0080 (4)0.0124 (4)0.0028 (4)
C8A0.0401 (8)0.0288 (7)0.0350 (8)0.0024 (6)0.0032 (6)0.0063 (6)
O1B0.0391 (6)0.0258 (5)0.0311 (5)0.0065 (4)0.0091 (4)0.0038 (4)
C1B0.0253 (6)0.0226 (6)0.0232 (6)0.0004 (5)0.0001 (5)0.0009 (5)
C2B0.0243 (6)0.0259 (7)0.0215 (6)0.0026 (5)0.0032 (5)0.0017 (5)
C3B0.0254 (6)0.0220 (6)0.0218 (6)0.0036 (5)0.0002 (5)0.0036 (5)
C4B0.0227 (6)0.0217 (6)0.0201 (6)0.0021 (5)0.0021 (5)0.0011 (5)
C5B0.0276 (6)0.0277 (7)0.0193 (6)0.0020 (5)0.0030 (5)0.0012 (5)
C6B0.0340 (7)0.0236 (7)0.0217 (6)0.0014 (5)0.0027 (5)0.0045 (5)
N1B0.0241 (5)0.0223 (6)0.0229 (5)0.0005 (4)0.0025 (4)0.0019 (4)
C7B0.0248 (6)0.0300 (7)0.0215 (6)0.0001 (5)0.0013 (5)0.0010 (5)
O2B0.0311 (5)0.0378 (6)0.0367 (6)0.0047 (4)0.0113 (4)0.0121 (5)
C8B0.0316 (7)0.0323 (8)0.0328 (7)0.0059 (6)0.0036 (6)0.0016 (6)
N1S0.0398 (7)0.0270 (6)0.0304 (6)0.0043 (5)0.0097 (5)0.0038 (5)
C2S0.0387 (7)0.0324 (8)0.0267 (7)0.0083 (6)0.0010 (6)0.0045 (6)
C3S0.0270 (6)0.0284 (7)0.0304 (7)0.0009 (5)0.0027 (5)0.0021 (6)
C4S0.0239 (6)0.0194 (6)0.0256 (6)0.0026 (5)0.0010 (5)0.0000 (5)
C5S0.0239 (6)0.0251 (7)0.0280 (7)0.0021 (5)0.0000 (5)0.0001 (5)
C6S0.0275 (6)0.0245 (7)0.0355 (7)0.0004 (5)0.0085 (6)0.0007 (6)
C7S0.0273 (6)0.0200 (6)0.0256 (6)0.0012 (5)0.0001 (5)0.0002 (5)
C8S0.0282 (7)0.0433 (9)0.0451 (9)0.0045 (6)0.0066 (6)0.0146 (7)
C9S0.0327 (8)0.0440 (9)0.0506 (10)0.0120 (7)0.0003 (7)0.0133 (8)
N10S0.0447 (7)0.0268 (6)0.0352 (7)0.0077 (5)0.0007 (5)0.0047 (5)
C11S0.0439 (8)0.0296 (8)0.0344 (8)0.0050 (6)0.0089 (6)0.0083 (6)
C12S0.0315 (7)0.0284 (7)0.0320 (7)0.0052 (6)0.0065 (6)0.0048 (6)
N1T0.0317 (6)0.0233 (6)0.0242 (5)0.0023 (5)0.0001 (4)0.0007 (4)
C2T0.0309 (7)0.0235 (6)0.0250 (6)0.0017 (5)0.0036 (5)0.0009 (5)
C3T0.0242 (6)0.0248 (6)0.0256 (6)0.0005 (5)0.0002 (5)0.0006 (5)
C4T0.0266 (6)0.0178 (6)0.0207 (6)0.0025 (5)0.0016 (5)0.0025 (5)
C5T0.0254 (6)0.0230 (6)0.0300 (7)0.0004 (5)0.0039 (5)0.0021 (5)
C6T0.0247 (6)0.0276 (7)0.0309 (7)0.0017 (5)0.0017 (5)0.0005 (6)
C7T0.0286 (6)0.0174 (6)0.0218 (6)0.0010 (5)0.0003 (5)0.0015 (5)
C8T0.0314 (7)0.0307 (7)0.0262 (6)0.0071 (6)0.0060 (5)0.0033 (6)
C9T0.0340 (7)0.0328 (8)0.0312 (7)0.0111 (6)0.0018 (6)0.0027 (6)
N10T0.0403 (7)0.0300 (6)0.0280 (6)0.0062 (5)0.0008 (5)0.0042 (5)
C12T0.0284 (6)0.0238 (7)0.0268 (6)0.0027 (5)0.0039 (5)0.0000 (5)
C11T0.0384 (7)0.0295 (7)0.0253 (7)0.0007 (6)0.0059 (6)0.0032 (6)
Geometric parameters (Å, º) top
O1A—C1A1.3575 (16)N1S—C2S1.336 (2)
O1A—H11A0.907 (19)C2S—C3S1.3849 (19)
C1A—C6A1.3894 (17)C2S—H2S0.9500
C1A—C2A1.3957 (18)C3S—C4S1.3890 (19)
C2A—C3A1.3811 (19)C3S—H3S0.9500
C2A—H2A0.9500C4S—C5S1.3915 (18)
C3A—C4A1.3965 (16)C4S—C7S1.4863 (17)
C3A—H3A0.9500C5S—C6S1.3860 (18)
C4A—C5A1.3941 (17)C5S—H5S0.9500
C4A—N1A1.4190 (16)C6S—H6S0.9500
C5A—C6A1.3819 (18)C7S—C12S1.3839 (19)
C5A—H5A0.9500C7S—C8S1.3930 (19)
C6A—H6A0.9500C8S—C9S1.379 (2)
N1A—C7A1.3458 (16)C8S—H9S0.9500
N1A—H1A0.884 (18)C9S—N10S1.331 (2)
C7A—O2A1.2353 (16)C9S—H8S0.9483
C7A—C8A1.5041 (19)N10S—C11S1.3362 (19)
C8A—H8A30.9800C11S—C12S1.3786 (19)
C8A—H8A10.9800C11S—H12S0.9500
C8A—H8A20.9800C12S—H11S0.9481
O1B—C1B1.3697 (15)N1T—C6T1.3379 (17)
O1B—H11B0.883 (19)N1T—C2T1.3383 (17)
C1B—C2B1.3883 (18)C2T—C3T1.3801 (18)
C1B—C6B1.3908 (17)C2T—H2T0.9500
C2B—C3B1.3852 (18)C3T—C4T1.3905 (18)
C2B—H2B0.9500C3T—H3T0.9500
C3B—C4B1.3932 (16)C4T—C5T1.3928 (17)
C3B—H3B0.9500C4T—C7T1.4826 (17)
C4B—C5B1.3905 (18)C5T—C6T1.3813 (18)
C4B—N1B1.4259 (16)C5T—H5T0.9500
C5B—C6B1.3849 (18)C6T—H6T0.9500
C5B—H5B0.9500C7T—C12T1.3894 (18)
C6B—H6B0.9500C7T—C8T1.3909 (18)
N1B—C7B1.3455 (16)C8T—C9T1.3834 (19)
N1B—H1B0.920 (18)C8T—H8T0.9500
C7B—O2B1.2363 (16)C9T—N10T1.3330 (19)
C7B—C8B1.5066 (19)C9T—H9T0.9500
C8B—H8B30.9800N10T—C11T1.3394 (18)
C8B—H8B20.9800C12T—C11T1.3851 (19)
C8B—H8B10.9800C12T—H12T0.9500
N1S—C6S1.332 (2)C11T—H11T0.9500
C1A—O1A—H11A109.2 (12)N1S—C2S—C3S123.91 (13)
O1A—C1A—C6A117.84 (11)N1S—C2S—H2S118.0
O1A—C1A—C2A123.61 (11)C3S—C2S—H2S118.0
C6A—C1A—C2A118.55 (12)C2S—C3S—C4S119.52 (13)
C3A—C2A—C1A120.06 (11)C2S—C3S—H3S120.2
C3A—C2A—H2A120.0C4S—C3S—H3S120.2
C1A—C2A—H2A120.0C3S—C4S—C5S116.93 (12)
C2A—C3A—C4A121.35 (12)C3S—C4S—C7S121.43 (12)
C2A—C3A—H3A119.3C5S—C4S—C7S121.63 (12)
C4A—C3A—H3A119.3C6S—C5S—C4S119.21 (13)
C5A—C4A—C3A118.46 (12)C6S—C5S—H5S120.4
C5A—C4A—N1A124.38 (11)C4S—C5S—H5S120.4
C3A—C4A—N1A117.11 (11)N1S—C6S—C5S124.22 (13)
C6A—C5A—C4A120.05 (11)N1S—C6S—H6S117.9
C6A—C5A—H5A120.0C5S—C6S—H6S117.9
C4A—C5A—H5A120.0C12S—C7S—C8S116.76 (12)
C5A—C6A—C1A121.53 (12)C12S—C7S—C4S121.54 (12)
C5A—C6A—H6A119.2C8S—C7S—C4S121.70 (12)
C1A—C6A—H6A119.2C9S—C8S—C7S119.25 (14)
C7A—N1A—C4A128.22 (11)C9S—C8S—H9S120.4
C7A—N1A—H1A118.0 (11)C7S—C8S—H9S120.4
C4A—N1A—H1A113.7 (11)N10S—C9S—C8S124.22 (14)
O2A—C7A—N1A123.41 (13)N10S—C9S—H8S118.2
O2A—C7A—C8A121.09 (12)C8S—C9S—H8S117.6
N1A—C7A—C8A115.50 (12)C9S—N10S—C11S116.18 (12)
C7A—C8A—H8A3109.5N10S—C11S—C12S123.77 (14)
C7A—C8A—H8A1109.5N10S—C11S—H12S118.1
H8A3—C8A—H8A1109.5C12S—C11S—H12S118.1
C7A—C8A—H8A2109.5C11S—C12S—C7S119.82 (13)
H8A3—C8A—H8A2109.5C11S—C12S—H11S119.8
H8A1—C8A—H8A2109.5C7S—C12S—H11S120.4
C1B—O1B—H11B107.9 (13)C6T—N1T—C2T116.30 (11)
O1B—C1B—C2B122.84 (11)N1T—C2T—C3T123.67 (12)
O1B—C1B—C6B118.00 (12)N1T—C2T—H2T118.2
C2B—C1B—C6B119.16 (12)C3T—C2T—H2T118.2
C3B—C2B—C1B119.86 (11)C2T—C3T—C4T119.66 (12)
C3B—C2B—H2B120.1C2T—C3T—H3T120.2
C1B—C2B—H2B120.1C4T—C3T—H3T120.2
C2B—C3B—C4B121.19 (12)C3T—C4T—C5T117.07 (12)
C2B—C3B—H3B119.4C3T—C4T—C7T120.47 (11)
C4B—C3B—H3B119.4C5T—C4T—C7T122.46 (12)
C5B—C4B—C3B118.69 (12)C6T—C5T—C4T119.06 (12)
C5B—C4B—N1B124.25 (11)C6T—C5T—H5T120.5
C3B—C4B—N1B117.06 (11)C4T—C5T—H5T120.5
C6B—C5B—C4B120.18 (11)N1T—C6T—C5T124.18 (12)
C6B—C5B—H5B119.9N1T—C6T—H6T117.9
C4B—C5B—H5B119.9C5T—C6T—H6T117.9
C5B—C6B—C1B120.90 (12)C12T—C7T—C8T117.09 (12)
C5B—C6B—H6B119.6C12T—C7T—C4T122.05 (11)
C1B—C6B—H6B119.6C8T—C7T—C4T120.85 (12)
C7B—N1B—C4B127.85 (11)C9T—C8T—C7T119.29 (13)
C7B—N1B—H1B116.0 (10)C9T—C8T—H8T120.4
C4B—N1B—H1B116.0 (10)C7T—C8T—H8T120.4
O2B—C7B—N1B123.14 (12)N10T—C9T—C8T124.25 (13)
O2B—C7B—C8B121.50 (11)N10T—C9T—H9T117.9
N1B—C7B—C8B115.36 (12)C8T—C9T—H9T117.9
C7B—C8B—H8B3109.5C9T—N10T—C11T116.05 (12)
C7B—C8B—H8B2109.5C11T—C12T—C7T119.28 (12)
H8B3—C8B—H8B2109.5C11T—C12T—H12T120.4
C7B—C8B—H8B1109.5C7T—C12T—H12T120.4
H8B3—C8B—H8B1109.5N10T—C11T—C12T124.04 (13)
H8B2—C8B—H8B1109.5N10T—C11T—H11T118.0
C6S—N1S—C2S116.19 (12)C12T—C11T—H11T118.0
(pmor02) top
Crystal data top
2[C8H9NO2][C4H9NO]Dx = 1.327 Mg m3
Mr = 389.45Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 3801 reflections
a = 7.2791 (9) Åθ = 2.5–24.5°
b = 14.6277 (18) ŵ = 0.10 mm1
c = 18.303 (2) ÅT = 150 K
V = 1948.9 (4) Å3Block, colourless
Z = 40.54 × 0.52 × 0.28 mm
F(000) = 832
Data collection top
CCD area detector
diffractometer
4733 independent reflections
Radiation source: fine-focus sealed tube4265 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
phi and ω scansθmax = 29.0°, θmin = 1.8°
Absorption correction: multi-scan
SADABS
h = 97
Tmin = 0.868, Tmax = 1k = 1918
12312 measured reflectionsl = 2422
Refinement top
Refinement on F2Hydrogen site location: geom/difmap
Least-squares matrix: fullNoref/refall
R[F2 > 2σ(F2)] = 0.046 w = 1/[σ2(Fo2) + (0.049P)2 + 0.2716P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.103(Δ/σ)max = 0.001
S = 1.07Δρmax = 0.26 e Å3
4733 reflectionsΔρmin = 0.27 e Å3
276 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0031 (7)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.4 (9)
Crystal data top
2[C8H9NO2][C4H9NO]V = 1948.9 (4) Å3
Mr = 389.45Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.2791 (9) ŵ = 0.10 mm1
b = 14.6277 (18) ÅT = 150 K
c = 18.303 (2) Å0.54 × 0.52 × 0.28 mm
Data collection top
CCD area detector
diffractometer
4733 independent reflections
Absorption correction: multi-scan
SADABS
4265 reflections with I > 2σ(I)
Tmin = 0.868, Tmax = 1Rint = 0.031
12312 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.046Noref/refall
wR(F2) = 0.103Δρmax = 0.26 e Å3
S = 1.07Δρmin = 0.27 e Å3
4733 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
276 parametersAbsolute structure parameter: 0.4 (9)
0 restraints
Special details top

Experimental. INTENSITY STATISTICS FOR DATASET # 1 pmor02.hkl

Resolution #Data #Theory %Complete Redundancy Mean I Mean I/s R(int) R(sigma)

Inf - 2.20 142 142 100.0 5.41 350.2 63.91 0.0176 0.0147 2.20 - 1.70 141 141 100.0 6.35 135.2 58.72 0.0191 0.0136 1.70 - 1.45 149 149 100.0 6.33 59.1 45.19 0.0325 0.0170 1.45 - 1.30 159 159 100.0 5.88 38.4 34.45 0.0430 0.0223 1.30 - 1.20 144 144 100.0 5.47 41.5 31.37 0.0411 0.0237 1.20 - 1.10 202 202 100.0 5.17 49.8 31.51 0.0381 0.0237 1.10 - 1.00 302 302 100.0 4.67 27.4 22.25 0.0498 0.0355 1.00 - 0.95 187 187 100.0 4.48 17.5 16.39 0.0672 0.0475 0.95 - 0.90 230 230 100.0 4.24 14.0 13.41 0.0755 0.0586 0.90 - 0.85 297 297 100.0 3.94 12.3 11.44 0.0874 0.0694 0.85 - 0.80 366 366 100.0 3.69 8.7 8.76 0.1217 0.0981 0.80 - 0.75 426 468 91.0 2.55 7.8 6.34 0.1369 0.1378 0.75 - 0.73 44 169 26.0 0.30 6.2 3.31 0.1658 0.2426 —————————————————————————— 0.85 - 0.73 836 1003 83.3 2.59 8.1 7.24 0.1286 0.1234 Inf - 0.73 2789 2956 94.4 4.18 44.8 22.51 0.0338 0.0271

Merged [A], lowest resolution = 18.30 Angstroms, 370 outliers downweighted

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. Final SHELX. res file:

TITL Parmor02 in P2(1)2(1)2(1) CELL 0.71073 7.2791 14.6277 18.3032 90.000 90.000 90.000 ZERR 4.00 0.0009 0.0018 0.0023 0.000 0.000 0.000 L A T T -1 SYMM 0.5-X, –Y, 0.5+Z SYMM –X, 0.5+Y, 0.5-Z SYMM 0.5+X, 0.5-Y, –Z SFAC C H N O UNIT 80 108 12 20 TEMP -123

L.S. 4 BOND $h FMAP 2 PLAN 20

ACTA

HTAB EQIV $1 x + 1/2, -y + 3/2, -z EQIV $2 x + 1/2, -y + 1/2, -z EQIV $3 - x + 1, y + 1/2, -z + 1/2 EQIV $4 - x + 1, y - 1/2, -z + 1/2

RTAB D1 H11A O1B_$1 RTAB D2 H1A O2B_$2 RTAB D3 H11B N4S_$3 RTAB D4 H1B O2A_$4

WGHT 0.049000 0.271600 EXTI 0.003119 FVAR 0.38623 O1A 4 0.684368 0.964657 - 0.096079 11.00000 0.05360 0.01939 = 0.03008 0.00317 0.00925 0.00229 H11A 2 0.728882 0.975094 - 0.134082 11.00000 0.03962 C1A 1 0.681417 0.871647 - 0.088611 11.00000 0.03135 0.01834 = 0.02183 0.00208 - 0.00409 0.00130 C2A 1 0.772462 0.813177 - 0.135815 11.00000 0.02986 0.02444 = 0.01677 0.00171 - 0.00017 - 0.00295 AFIX 43 H2A 2 0.841154 0.837252 - 0.175532 11.00000 - 1.20000 AFIX 0 C3A 1 0.763297 0.719539 - 0.125074 11.00000 0.02638 0.02274 = 0.01726 - 0.00393 - 0.00124 0.00246 AFIX 43 H3A 2 0.825764 0.679696 - 0.157677 11.00000 - 1.20000 AFIX 0 C4A 1 0.663851 0.683270 - 0.067204 11.00000 0.02404 0.01662 = 0.01737 - 0.00068 - 0.00409 0.00003 C5A 1 0.573082 0.742218 - 0.019899 11.00000 0.02552 0.02418 = 0.01986 0.00138 0.00241 - 0.00036 AFIX 43 H5A 2 0.503990 0.718323 0.019779 11.00000 - 1.20000 AFIX 0 C6A 1 0.583266 0.835604 - 0.030542 11.00000 0.03086 0.02214 = 0.02254 - 0.00317 0.00286 0.00407 AFIX 43 H6A 2 0.522190 0.875573 0.002377 11.00000 - 1.20000 AFIX 0 N1A 3 0.655604 0.586523 - 0.058446 11.00000 0.03098 0.01727 = 0.01662 - 0.00289 0.00083 - 0.00021 H1A 2 0.670516 0.553839 - 0.097141 11.00000 0.01612 C7A 1 0.654400 0.542181 0.006368 11.00000 0.02509 0.01989 = 0.02187 - 0.00016 - 0.00141 0.00114 O2A 4 0.657722 0.581331 0.065354 11.00000 0.04985 0.02615 = 0.01647 - 0.00079 - 0.00140 0.00244 C8A 1 0.646350 0.439601 0.002039 11.00000 0.04473 0.02178 = 0.02270 0.00277 0.00038 - 0.00324 AFIX 137 H8A1 2 0.744793 0.413333 0.031929 11.00000 - 1.50000 H8A2 2 0.661862 0.420282 - 0.048856 11.00000 - 1.50000 H8A3 2 0.527150 0.418336 0.020225 11.00000 - 1.50000 AFIX 0 O1B 4 0.312197 0.479265 0.229917 11.00000 0.05311 0.01611 = 0.02213 0.00115 - 0.00395 - 0.00168 H11B 2 0.310887 0.512982 0.269807 11.00000 0.06211 C1B 1 0.290108 0.388328 0.244542 11.00000 0.02476 0.01786 = 0.02451 0.00143 - 0.00225 - 0.00066 C2B 1 0.268149 0.355416 0.314840 11.00000 0.03539 0.01977 = 0.02036 - 0.00589 - 0.00156 0.00147 AFIX 43 H2B 2 0.266227 0.396817 0.354823 11.00000 - 1.20000 AFIX 0 C3B 1 0.249022 0.262926 0.327306 11.00000 0.03311 0.02416 = 0.01526 0.00007 0.00069 0.00061 AFIX 43 H3B 2 0.235502 0.241171 0.375915 11.00000 - 1.20000 AFIX 0 C4B 1 0.249289 0.201026 0.269482 11.00000 0.02150 0.01833 = 0.01983 0.00032 - 0.00086 - 0.00068 C5B 1 0.267434 0.234368 0.198471 11.00000 0.02753 0.02035 = 0.01750 - 0.00325 0.00063 0.00173 AFIX 43 H5B 2 0.264667 0.193348 0.158247 11.00000 - 1.20000 AFIX 0 C6B 1 0.289501 0.327280 0.186510 11.00000 0.02869 0.02308 = 0.01915 0.00333 - 0.00130 0.00184 AFIX 43 H6B 2 0.304369 0.349407 0.138071 11.00000 - 1.20000 AFIX 0 N1B 3 0.230941 0.107595 0.288277 11.00000 0.04024 0.01875 = 0.01364 0.00214 - 0.00078 - 0.00095 H1B 2 0.236952 0.098229 0.331015 11.00000 0.01656 C7B 1 0.219446 0.033968 0.245143 11.00000 0.02424 0.02045 = 0.02136 - 0.00073 - 0.00111 0.00152 O2B 4 0.224652 0.037542 0.178026 11.00000 0.05285 0.02159 = 0.01746 - 0.00241 - 0.00125 0.00095 C8B 1 0.200253 - 0.055618 0.285535 11.00000 0.04018 0.02008 = 0.02583 0.00134 - 0.00001 - 0.00230 AFIX 137 H8B1 2 0.116495 - 0.095887 0.258674 11.00000 - 1.50000 H8B2 2 0.150894 - 0.044183 0.334504 11.00000 - 1.50000 H8B3 2 0.320922 - 0.084885 0.289623 11.00000 - 1.50000 AFIX 0 O1S 4 0.773987 0.199213 0.032972 11.00000 0.03952 0.02962 = 0.03003 0.00750 0.00480 0.00160 C2S 1 0.796539 0.235387 0.104383 11.00000 0.04546 0.02629 = 0.03528 0.00609 0.00102 - 0.00579 AFIX 23 H2S1 2 0.688901 0.273750 0.116758 11.00000 - 1.20000 H2S2 2 0.907064 0.274802 0.105521 11.00000 - 1.20000 AFIX 0 C3S 1 0.816430 0.160129 0.160961 11.00000 0.03458 0.03000 = 0.03052 0.00350 - 0.00049 - 0.00424 AFIX 23 H3S1 2 0.931206 0.125783 0.151547 11.00000 - 1.20000 H3S2 2 0.825856 0.187871 0.210154 11.00000 - 1.20000 AFIX 0 N4S 3 0.659242 0.096303 0.159458 11.00000 0.02616 0.02177 = 0.02616 0.00299 0.00190 0.00223 H4S 2 0.559277 0.123433 0.172051 11.00000 0.03139 C5S 1 0.629024 0.064199 0.084051 11.00000 0.03861 0.02359 = 0.02701 0.00241 - 0.00150 - 0.00058 AFIX 23 H5S1 2 0.514320 0.027907 0.082202 11.00000 - 1.20000 H5S2 2 0.731756 0.023723 0.069559 11.00000 - 1.20000 AFIX 0 C6S 1 0.615312 0.142908 0.030117 11.00000 0.03884 0.03120 = 0.02574 0.00423 - 0.00225 0.00313 AFIX 23 H6S1 2 0.600853 0.118252 - 0.019926 11.00000 - 1.20000 H6S2 2 0.505302 0.180056 0.041524 11.00000 - 1.20000

HKLF 4 1 - 1 0 0 0 0 - 1 0 - 1 0

REM Parmor02 in P2(1)2(1)2(1) REM R1 = 0.0462 for 4265 Fo > 4sig(Fo) and 0.0517 for all 4733 data REM 276 parameters refined using 0 restraints

END

WGHT 0.0494 0.2663 REM Highest difference peak 0.256, deepest hole -0.270, 1-σ level 0.059 Q1 1 0.5696 0.8556 - 0.0736 11.00000 0.05 0.26 Q2 1 0.6468 0.7126 - 0.0365 11.00000 0.05 0.25 Q3 1 0.5639 0.7040 - 0.0560 11.00000 0.05 0.23 Q4 1 0.2433 0.3599 0.2134 11.00000 0.05 0.22 Q5 1 0.2626 0.2331 0.2975 11.00000 0.05 0.22 Q6 1 0.6583 0.8389 - 0.1255 11.00000 0.05 0.22 Q7 1 0.6167 0.1054 0.0581 11.00000 0.05 0.22 Q8 1 0.6709 0.8554 - 0.0461 11.00000 0.05 0.21 Q9 1 0.5525 0.7852 - 0.0496 11.00000 0.05 0.21 Q10 1 0.6519 0.4827 - 0.0081 11.00000 0.05 0.21 Q11 1 0.6351 0.7925 - 0.0183 11.00000 0.05 0.20 Q12 1 0.2123 0.1613 0.2747 11.00000 0.05 0.20 Q13 1 0.4806 0.8644 - 0.0236 11.00000 0.05 0.20 Q14 1 0.1667 - 0.0014 0.2689 11.00000 0.05 0.20 Q15 1 0.6210 0.5645 - 0.0236 11.00000 0.05 0.20 Q16 1 0.1927 0.3142 0.3124 11.00000 0.05 0.19 Q17 1 0.7839 0.8405 - 0.0929 11.00000 0.05 0.19 Q18 1 0.7778 0.2006 0.1360 11.00000 0.05 0.19 Q19 1 0.3788 0.3569 0.2223 11.00000 0.05 0.19 Q20 1 0.5635 0.9808 - 0.1079 11.00000 0.05 0.19

#=============================================================================== # PLATON/CHECK-(191101) versus check.def version of 16/11/01 for entry: pmor02 # Data From: pmor02.cif - Data Type: CIF Bond Precision C—C = 0.0022 A # # CELL 0.71073 7.279 14.628 18.303 90.00 90.00 90.00 1948.80 # SpaceGroup from Symmetry P212121 Hall: P 2ac 2ab # Reported P2(1)2(1)2 (? # MoietyFormula 2(C8 H9 N O2), C4 H9 N O # Reported 2[C8H9NO2][C4H9O] # SumFormula C20 H27 N3 O5 # Reported C20 H27 N3 O5 # Mr = 389.45[Calc], 389.45[Rep] # Dx,gcm-3 = 1.327[Calc], 1.327[Rep] # Z = 4[Calc], 4[Rep] # Mu (mm-1) = 0.096[Calc], 0.096[Rep] # F000 = 832.0[Calc], 832.0[Rep] # Reported T limits: Tmin=0.868 Tmax=1.000 'MULTISCAN' # Calculated T limits: Tmin=0.949 Tmin'=0.949 Tmax=0.973 # Reported Hmax= 9, Kmax= 19, Lmax= 24, Nref= 4733, Th(max)= 28.97 # Calculated Hmax= 9, Kmax= 19, Lmax= 24, Nref= 2929 (5154), Ratio= 1.62 (0.92) # R= 0.0462 (4265), wR2= 0.1028 (4733), S = 1.066, Npar= 276, Flack= 0.4 (9) #===============================================================================

>>> The Following ALERTS were generated <<<

024_ALERT C Merging of Friedel Data preferred for ZSi.. !

SHELX defaults accepted here; mering or not should not matter provided the data are correctly weighted.

032_ALERT C Std Uncertainty in Flack parameter too high.. 0.90 033_ALERT C Flack Parameter value deviates from zero ···.. 0.40

CHNO structure; Mo radiation. The Flack parameter is undetermined.

042_ALERT C Calc. and Rep. MoietyFormula Strings Differ.. ?

No they don't

061_ALERT C Tmax/Tmin Range Test RR' too large ·········.. 0.89 062_ALERT C Rescale T(min) & T(max) by ··················. 0.97

SADABS corrects for all systematic errors, not just crystal absorption. Extra absorption may come from glue, glass fibre etc.

125_ALERT C No _symmetry_space_group_name_Hall given ···.. ?

P 2ac 2ab

223_ALERT C Large Solvent/Anion H Ueq(max)/Ueq(min). 3.88 Ratio

Where? Diagonalized Uij tensor components listed below. There doesn't seem to be a problem.

0.0571 0.0275 0.0185 O1A 0.0329 0.0219 0.0167 C1A 0.0312 0.0235 0.0164 C2A 0.0284 0.0227 0.0152 C3A 0.0260 0.0169 0.0152 C4A 0.0264 0.0245 0.0186 C5A 0.0327 0.0255 0.0174 C6A 0.0310 0.0198 0.0140 N1A 0.0258 0.0214 0.0196 C7A 0.0502 0.0259 0.0164 O2A 0.0452 0.0249 0.0191 C8A 0.0537 0.0218 0.0159 O1B 0.0271 0.0224 0.0176 C1B 0.0359 0.0255 0.0142 C2B 0.0332 0.0241 0.0152 C3B 0.0220 0.0195 0.0182 C4B 0.0279 0.0222 0.0152 C5B 0.0293 0.0248 0.0169 C6B 0.0403 0.0195 0.0129 N1B 0.0252 0.0210 0.0198 C7B 0.0529 0.0226 0.0163 O2B 0.0404 0.0261 0.0195 C8B 0.0433 0.0339 0.0220 O1S 0.0471 0.0380 0.0219 C2S 0.0378 0.0315 0.0257 C3S 0.0298 0.0243 0.0200 N4S 0.0389 0.0280 0.0223 C5S 0.0400 0.0331 0.0227 C6S

420_ALERT C D—H Without Acceptor N(4S) - H(4S) ?

See text. ALERT Level Summary 9 ALERT Level C = Check & Explain

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1A0.6844 (2)0.96466 (8)0.09608 (8)0.0344 (3)
H11A0.729 (4)0.9751 (14)0.1341 (13)0.040 (6)*
C1A0.6814 (3)0.87165 (11)0.08861 (9)0.0238 (4)
C2A0.7725 (3)0.81318 (11)0.13581 (8)0.0237 (4)
H2A0.84120.83730.17550.028*
C3A0.7633 (2)0.71954 (11)0.12507 (8)0.0221 (3)
H3A0.82580.67970.15770.027*
C4A0.6639 (2)0.68327 (10)0.06720 (8)0.0193 (3)
C5A0.5731 (2)0.74222 (11)0.01990 (9)0.0232 (4)
H5A0.50400.71830.01980.028*
C6A0.5833 (3)0.83560 (11)0.03054 (9)0.0252 (4)
H6A0.52220.87560.00240.030*
N1A0.6556 (2)0.58652 (9)0.05845 (7)0.0216 (3)
H1A0.671 (3)0.5538 (11)0.0971 (10)0.016 (4)*
C7A0.6544 (2)0.54218 (11)0.00637 (9)0.0223 (3)
O2A0.6577 (2)0.58133 (8)0.06535 (6)0.0308 (3)
C8A0.6464 (3)0.43960 (11)0.00204 (9)0.0297 (4)
H8A10.74480.41330.03190.045*
H8A20.66190.42030.04890.045*
H8A30.52720.41830.02020.045*
O1B0.3122 (2)0.47926 (8)0.22992 (7)0.0304 (3)
H11B0.311 (4)0.5130 (18)0.2698 (14)0.062 (8)*
C1B0.2901 (2)0.38833 (10)0.24454 (9)0.0224 (3)
C2B0.2681 (3)0.35542 (11)0.31484 (9)0.0252 (4)
H2B0.26620.39680.35480.030*
C3B0.2490 (3)0.26293 (11)0.32731 (8)0.0242 (4)
H3B0.23550.24120.37590.029*
C4B0.2493 (2)0.20103 (10)0.26948 (8)0.0199 (3)
C5B0.2674 (2)0.23437 (10)0.19847 (8)0.0218 (3)
H5B0.26470.19330.15820.026*
C6B0.2895 (3)0.32728 (11)0.18651 (9)0.0236 (4)
H6B0.30440.34940.13810.028*
N1B0.2309 (2)0.10760 (9)0.28828 (7)0.0242 (3)
H1B0.237 (3)0.0982 (11)0.3310 (10)0.017 (4)*
C7B0.2194 (2)0.03397 (10)0.24514 (9)0.0220 (3)
O2B0.2247 (2)0.03754 (8)0.17803 (6)0.0306 (3)
C8B0.2003 (3)0.05562 (11)0.28553 (9)0.0287 (4)
H8B10.11650.09590.25870.043*
H8B20.15090.04420.33450.043*
H8B30.32090.08490.28960.043*
O1S0.7740 (2)0.19921 (8)0.03297 (7)0.0331 (3)
C2S0.7965 (3)0.23539 (12)0.10438 (11)0.0357 (5)
H2S10.68890.27380.11680.043*
H2S20.90710.27480.10550.043*
C3S0.8164 (3)0.16013 (12)0.16096 (10)0.0317 (4)
H3S10.93120.12580.15150.038*
H3S20.82590.18790.21020.038*
N4S0.6592 (2)0.09630 (10)0.15946 (8)0.0247 (3)
H4S0.559 (3)0.1234 (14)0.1721 (11)0.031 (6)*
C5S0.6290 (3)0.06420 (12)0.08405 (9)0.0297 (4)
H5S10.51430.02790.08220.036*
H5S20.73180.02370.06960.036*
C6S0.6153 (3)0.14291 (13)0.03012 (10)0.0319 (4)
H6S10.60090.11830.01990.038*
H6S20.50530.18010.04150.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0536 (10)0.0194 (6)0.0301 (7)0.0023 (6)0.0093 (7)0.0032 (5)
C1A0.0314 (10)0.0183 (7)0.0218 (8)0.0013 (7)0.0041 (7)0.0021 (6)
C2A0.0299 (9)0.0244 (8)0.0168 (7)0.0030 (7)0.0002 (7)0.0017 (6)
C3A0.0264 (9)0.0227 (8)0.0173 (7)0.0025 (7)0.0012 (7)0.0039 (6)
C4A0.0240 (8)0.0166 (7)0.0174 (7)0.0000 (6)0.0041 (6)0.0007 (6)
C5A0.0255 (9)0.0242 (8)0.0199 (8)0.0004 (7)0.0024 (6)0.0014 (7)
C6A0.0309 (10)0.0221 (8)0.0225 (8)0.0041 (7)0.0029 (7)0.0032 (7)
N1A0.0310 (8)0.0173 (6)0.0166 (6)0.0002 (6)0.0008 (6)0.0029 (5)
C7A0.0251 (9)0.0199 (7)0.0219 (8)0.0011 (7)0.0014 (7)0.0002 (6)
O2A0.0499 (8)0.0262 (6)0.0165 (5)0.0024 (6)0.0014 (6)0.0008 (5)
C8A0.0447 (11)0.0218 (8)0.0227 (8)0.0032 (8)0.0004 (8)0.0028 (7)
O1B0.0531 (9)0.0161 (5)0.0221 (6)0.0017 (6)0.0040 (6)0.0011 (5)
C1B0.0248 (9)0.0179 (7)0.0245 (8)0.0007 (7)0.0022 (7)0.0014 (6)
C2B0.0354 (10)0.0198 (7)0.0204 (8)0.0015 (7)0.0016 (7)0.0059 (6)
C3B0.0331 (10)0.0242 (8)0.0153 (7)0.0006 (8)0.0007 (7)0.0001 (6)
C4B0.0215 (8)0.0183 (7)0.0198 (7)0.0007 (7)0.0009 (6)0.0003 (6)
C5B0.0275 (9)0.0203 (7)0.0175 (7)0.0017 (7)0.0006 (7)0.0032 (6)
C6B0.0287 (9)0.0231 (8)0.0192 (7)0.0018 (7)0.0013 (7)0.0033 (6)
N1B0.0402 (9)0.0187 (6)0.0136 (6)0.0010 (6)0.0008 (6)0.0021 (5)
C7B0.0242 (8)0.0205 (7)0.0214 (7)0.0015 (7)0.0011 (7)0.0007 (6)
O2B0.0529 (9)0.0216 (5)0.0175 (5)0.0009 (6)0.0013 (6)0.0024 (4)
C8B0.0402 (11)0.0201 (8)0.0258 (8)0.0023 (8)0.0000 (8)0.0013 (7)
O1S0.0395 (8)0.0296 (6)0.0300 (6)0.0016 (6)0.0048 (6)0.0075 (5)
C2S0.0455 (13)0.0263 (9)0.0353 (10)0.0058 (9)0.0010 (9)0.0061 (8)
C3S0.0346 (11)0.0300 (9)0.0305 (9)0.0042 (8)0.0005 (8)0.0035 (8)
N4S0.0262 (8)0.0218 (7)0.0262 (7)0.0022 (6)0.0019 (6)0.0030 (6)
C5S0.0386 (11)0.0236 (8)0.0270 (9)0.0006 (8)0.0015 (8)0.0024 (7)
C6S0.0388 (12)0.0312 (9)0.0257 (9)0.0031 (8)0.0023 (8)0.0042 (7)
Geometric parameters (Å, º) top
O1A—C1A1.3676 (19)C4B—C5B1.394 (2)
O1A—H11A0.78 (2)C4B—N1B1.4156 (19)
C1A—C2A1.385 (2)C5B—C6B1.386 (2)
C1A—C6A1.385 (2)C5B—H5B0.9500
C2A—C3A1.385 (2)C6B—H6B0.9500
C2A—H2A0.9500N1B—C7B1.338 (2)
C3A—C4A1.388 (2)N1B—H1B0.795 (18)
C3A—H3A0.9500C7B—O2B1.2302 (19)
C4A—C5A1.389 (2)C7B—C8B1.511 (2)
C4A—N1A1.4255 (18)C8B—H8B10.9800
C5A—C6A1.382 (2)C8B—H8B20.9800
C5A—H5A0.9500C8B—H8B30.9800
C6A—H6A0.9500O1S—C6S1.420 (2)
N1A—C7A1.352 (2)O1S—C2S1.420 (2)
N1A—H1A0.861 (18)C2S—C3S1.518 (2)
C7A—O2A1.2224 (19)C2S—H2S10.9900
C7A—C8A1.504 (2)C2S—H2S20.9900
C8A—H8A10.9800C3S—N4S1.477 (2)
C8A—H8A20.9800C3S—H3S10.9900
C8A—H8A30.9800C3S—H3S20.9900
O1B—C1B1.3663 (18)N4S—C5S1.474 (2)
O1B—H11B0.88 (3)N4S—H4S0.86 (2)
C1B—C2B1.383 (2)C5S—C6S1.520 (2)
C1B—C6B1.388 (2)C5S—H5S10.9900
C2B—C3B1.379 (2)C5S—H5S20.9900
C2B—H2B0.9500C6S—H6S10.9900
C3B—C4B1.393 (2)C6S—H6S20.9900
C3B—H3B0.9500
C1A—O1A—H11A106.8 (16)C6B—C5B—H5B120.0
O1A—C1A—C2A123.00 (16)C4B—C5B—H5B120.0
O1A—C1A—C6A117.62 (16)C5B—C6B—C1B120.70 (14)
C2A—C1A—C6A119.38 (15)C5B—C6B—H6B119.7
C1A—C2A—C3A119.94 (15)C1B—C6B—H6B119.7
C1A—C2A—H2A120.0C7B—N1B—C4B129.76 (14)
C3A—C2A—H2A120.0C7B—N1B—H1B116.4 (12)
C2A—C3A—C4A120.74 (15)C4B—N1B—H1B113.6 (12)
C2A—C3A—H3A119.6O2B—C7B—N1B123.58 (14)
C4A—C3A—H3A119.6O2B—C7B—C8B121.89 (14)
C3A—C4A—C5A119.10 (14)N1B—C7B—C8B114.53 (14)
C3A—C4A—N1A119.15 (14)C7B—C8B—H8B1109.5
C5A—C4A—N1A121.74 (15)C7B—C8B—H8B2109.5
C6A—C5A—C4A120.02 (16)H8B1—C8B—H8B2109.5
C6A—C5A—H5A120.0C7B—C8B—H8B3109.5
C4A—C5A—H5A120.0H8B1—C8B—H8B3109.5
C5A—C6A—C1A120.81 (16)H8B2—C8B—H8B3109.5
C5A—C6A—H6A119.6C6S—O1S—C2S110.13 (14)
C1A—C6A—H6A119.6O1S—C2S—C3S111.64 (15)
C7A—N1A—C4A125.11 (14)O1S—C2S—H2S1109.3
C7A—N1A—H1A117.1 (11)C3S—C2S—H2S1109.3
C4A—N1A—H1A117.0 (11)O1S—C2S—H2S2109.3
O2A—C7A—N1A123.37 (14)C3S—C2S—H2S2109.3
O2A—C7A—C8A120.98 (15)H2S1—C2S—H2S2108.0
N1A—C7A—C8A115.64 (14)N4S—C3S—C2S111.82 (16)
C7A—C8A—H8A1109.5N4S—C3S—H3S1109.3
C7A—C8A—H8A2109.5C2S—C3S—H3S1109.3
H8A1—C8A—H8A2109.5N4S—C3S—H3S2109.3
C7A—C8A—H8A3109.5C2S—C3S—H3S2109.3
H8A1—C8A—H8A3109.5H3S1—C3S—H3S2107.9
H8A2—C8A—H8A3109.5C5S—N4S—C3S109.53 (14)
C1B—O1B—H11B112.4 (16)C5S—N4S—H4S105.8 (14)
O1B—C1B—C2B122.33 (14)C3S—N4S—H4S111.0 (14)
O1B—C1B—C6B118.48 (14)N4S—C5S—C6S112.12 (14)
C2B—C1B—C6B119.19 (14)N4S—C5S—H5S1109.2
C3B—C2B—C1B120.47 (14)C6S—C5S—H5S1109.2
C3B—C2B—H2B119.8N4S—C5S—H5S2109.2
C1B—C2B—H2B119.8C6S—C5S—H5S2109.2
C2B—C3B—C4B120.79 (14)H5S1—C5S—H5S2107.9
C2B—C3B—H3B119.6O1S—C6S—C5S111.23 (16)
C4B—C3B—H3B119.6O1S—C6S—H6S1109.4
C3B—C4B—C5B118.75 (13)C5S—C6S—H6S1109.4
C3B—C4B—N1B116.28 (13)O1S—C6S—H6S2109.4
C5B—C4B—N1B124.97 (13)C5S—C6S—H6S2109.4
C6B—C5B—C4B120.08 (14)H6S1—C6S—H6S2108.0

Experimental details

(parody)(pardmp)(parnmm)(ppip02)
Crystal data
Chemical formula2[C8H9O2N]·[C4H8O2]2[C8H9NO2][C6H14N2]2[C8H9NO2][C5H11NO]2[C8H9NO2][C4H10N2]
Mr390.43416.52403.47388.46
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/cMonoclinic, P21/cMonoclinic, P21/c
Temperature (K)220150150150
a, b, c (Å)12.421 (5), 12.056 (4), 13.396 (3)10.6970 (9), 11.0240 (9), 9.4896 (8)10.5749 (8), 11.0221 (8), 9.3894 (7)15.893 (5), 5.1664 (17), 12.993 (4)
α, β, γ (°)90, 91.51 (3), 9090, 100.684 (2), 9090, 101.145 (2), 9090, 113.633 (5), 90
V3)2005.4 (11)1099.65 (16)1073.77 (14)977.4 (6)
Z4222
Radiation typeCu KαMo KαMo KαMo Kα
µ (mm1)0.800.090.090.09
Crystal size (mm)0.78 × 0.19 × 0.160.56 × 0.18 × 0.080.34 × 0.09 × 0.070.77 × 0.28 × 0.11
Data collection
Diffractometer?CCD area detector
diffractometer
?Bruker Smart Apex CCD
diffractometer
Absorption correctionEmpirical
Psi-scans
Multi-scan
SADABS
Multi-scan
SADABS
Multi-scan
SADABS
Tmin, Tmax0.602, 0.8260.833, 10.792, 0.9620.690, 1
No. of measured, independent and
observed [I > 2σ(I)] reflections
4865, 3499, 2508 7034, 2724, 2512 6517, 2444, 1890 5628, 2309, 1778
Rint0.0530.0160.0220.046
(sin θ/λ)max1)0.6090.6840.6490.672
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.070, 0.224, 1.08 0.053, 0.134, 1.06 0.041, 0.108, 0.97 0.078, 0.165, 1.18
No. of reflections3499272424442309
No. of parameters285146147140
No. of restraints60000
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementRiding/refallRiding/refallRiding/refall
Δρmax, Δρmin (e Å3)0.50, 0.260.40, 0.190.22, 0.220.34, 0.45
Absolute structure????
Absolute structure parameter????


(pardip)(pmor02)
Crystal data
Chemical formula[C8H9NO2][C10H8N2]2[C8H9NO2][C4H9NO]
Mr307.35389.45
Crystal system, space groupMonoclinic, P21/cOrthorhombic, P212121
Temperature (K)150150
a, b, c (Å)11.2906 (10), 24.103 (2), 11.5526 (10)7.2791 (9), 14.6277 (18), 18.303 (2)
α, β, γ (°)90, 96.1484 (16), 9090, 90, 90
V3)3125.8 (5)1948.9 (4)
Z84
Radiation typeMo KαMo Kα
µ (mm1)0.090.10
Crystal size (mm)0.46 × 0.28 × 0.180.54 × 0.52 × 0.28
Data collection
DiffractometerBruker SMART APEX CCD
diffractometer
CCD area detector
diffractometer
Absorption correctionMulti-scan
SADABS
Multi-scan
SADABS
Tmin, Tmax0.830, 10.868, 1
No. of measured, independent and
observed [I > 2σ(I)] reflections
20270, 7766, 6044 12312, 4733, 4265
Rint0.0220.031
(sin θ/λ)max1)0.6860.681
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.128, 1.04 0.046, 0.103, 1.07
No. of reflections77664733
No. of parameters433276
No. of restraints00
H-atom treatmentRiding/refallNoref/refall
Δρmax, Δρmin (e Å3)0.36, 0.250.26, 0.27
Absolute structure?Flack H D (1983), Acta Cryst. A39, 876-881
Absolute structure parameter?0.4 (9)

Computer programs: Stoe DIF4, Bruker SMART, Smart, SMART, Saint, Stoe REDU4, Bruker SAINT, Bruker SHELXTL, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL.

 

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