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A method to refine organic crystal structures from powder diffraction data with incorrect lattice parameters has been developed. The method is based on the similarity measure developed by de Gelder et al. [J. Comput. Chem. (2001), 22, 273-289], using the cross- and auto-correlation functions of a simulated and an experimental powder pattern. The lattice parameters, molecular position, molecular orientation and selected intramolecular degrees of freedom are optimized until the similarity measure reaches a maximum; subsequently, a Rietveld refinement is carried out. The program FIDEL (FIt with DEviating Lattice parameters) implements this method. The procedure is also suitable for unindexed powder data, powder diagrams of very low quality and powder diagrams of non-phase-pure samples. Various applications are shown, including structure determinations from powder data using crystal structure predictions by standard force-field methods. Other useful applications include the automatic structure determination from powder data starting from the crystal structures of isostructural compounds (e.g. a solvate, hydrate or chemical derivative), or from crystal data measured at a different temperature or pressure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520613033994/og5067sup1.cif
Contains datablocks I, II

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S2052520613033994/og5067Isup2.rtv
Contains datablock I

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S2052520613033994/og5067IIsup3.rtv
Contains datablock II

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520613033994/og5067sup4.pdf
Details of FIDEL fits and Rietveld refinements

CCDC references: 977561; 977562; 977563; 977564

Experimental top

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1.

Results and discussion top

Computing details top

For both compounds, data collection: STOE WinXPOW (STOE & Cie GmbH, 2006); cell refinement: TOPAS Academic (Coelho, 2007); data reduction: TOPAS Academic (Coelho, 2007); program(s) used to solve structure: FIDEL (Habermehl et al., 2014); program(s) used to refine structure: TOPAS Academic (Coelho, 2007).

Figures top
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[Figure 8]
[Figure 9]
[Figure 10]
(I) 4-(p-Chlorophenyl)-4-hydroxy-N,N-dimethyl-α,α-diphenyl-1-piperidinebutyramide hydrochloride top
Crystal data top
C29H34ClN2O2+·ClZ = 4
Mr = 513.48F(000) = 1088.0
Monoclinic, P21/cDx = 1.274 Mg m3
a = 16.7095 (8) ÅCu Kα1 radiation, λ = 1.54056 Å
b = 12.3773 (5) ŵ = 2.40 mm1
c = 13.2135 (5) ÅT = 298 K
β = 101.642 (3)°colourless
V = 2676.59 (19) Å3cylinder, 10 × 1 mm
Data collection top
STOE Stadi-P
diffractometer
Data collection mode: transmission
Radiation source: sealed x-ray tubeScan method: step
Primary focussing Ge 111 monochromator2θmin = 2.000°, 2θmax = 100.190°, 2θstep = 0.01°
Specimen mounting: glass capillary
Refinement top
Least-squares matrix: full with fixed elements per cycle259 parameters
Rp = 0.043201 restraints
Rwp = 0.0600 constraints
Rexp = 0.027All H-atom parameters refined
RBragg = 0.030Weighting scheme based on measured s.u.'s
χ2 = 5.081(Δ/σ)max = 0.001
9820 data pointsBackground function: Chebyshev with 20 terms
Profile function: modified Thompson-Cox-Hastings pseudo-VoigtPreferred orientation correction: none
Crystal data top
C29H34ClN2O2+·ClV = 2676.59 (19) Å3
Mr = 513.48Z = 4
Monoclinic, P21/cCu Kα1 radiation, λ = 1.54056 Å
a = 16.7095 (8) ŵ = 2.40 mm1
b = 12.3773 (5) ÅT = 298 K
c = 13.2135 (5) Åcylinder, 10 × 1 mm
β = 101.642 (3)°
Data collection top
STOE Stadi-P
diffractometer
Scan method: step
Specimen mounting: glass capillary2θmin = 2.000°, 2θmax = 100.190°, 2θstep = 0.01°
Data collection mode: transmission
Refinement top
Rp = 0.0439820 data points
Rwp = 0.060259 parameters
Rexp = 0.027201 restraints
RBragg = 0.030All H-atom parameters refined
χ2 = 5.081
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.5327 (3)0.0795 (3)0.8847 (3)0.05469
C20.3187 (2)0.3966 (3)0.4917 (3)0.04888
C30.3407 (2)0.2845 (3)0.4562 (3)0.04888
H40.3564 (9)0.4541 (10)0.4765 (10)0.05866
H50.3207 (10)0.3970 (11)0.5672 (9)0.05866
C60.2305 (3)0.4170 (3)0.4290 (3)0.04888
N70.4281 (3)0.2629 (3)0.5012 (3)0.04888
H80.3051 (10)0.2283 (10)0.4777 (10)0.05866
H90.3307 (11)0.2830 (10)0.3791 (9)0.05866
C100.1803 (4)0.3035 (4)0.4120 (3)0.04888
C110.1911 (2)0.5124 (3)0.4731 (3)0.04888
C120.2358 (3)0.4579 (2)0.3198 (3)0.04888
H130.4584 (11)0.3179 (10)0.4753 (11)0.05866
C140.4495 (2)0.2614 (4)0.6172 (3)0.04888
C150.4593 (2)0.1576 (3)0.4666 (3)0.04888
O160.1554 (6)0.2672 (6)0.3223 (5)0.04888
N170.1434 (3)0.2622 (5)0.4894 (3)0.04888
C180.1005 (2)0.5257 (3)0.4455 (3)0.04888
C190.2454 (2)0.5844 (3)0.5392 (2)0.04888
C200.1591 (3)0.4829 (3)0.2418 (3)0.04888
C210.3143 (3)0.4704 (3)0.2965 (3)0.04888
C220.5455 (3)0.2665 (3)0.6529 (3)0.04888
H230.4276 (9)0.1923 (10)0.6411 (9)0.05866
H240.4208 (10)0.3228 (10)0.6438 (9)0.05866
H250.4434 (11)0.1531 (11)0.3916 (9)0.05866
H260.4324 (9)0.0964 (10)0.4961 (10)0.05866
C270.5545 (3)0.1535 (4)0.5040 (3)0.04888
C280.1729 (3)0.2951 (3)0.5990 (3)0.04888
C290.0652 (3)0.1938 (3)0.4606 (3)0.04888
H300.0658 (9)0.4753 (11)0.4003 (10)0.05866
C310.0626 (2)0.6112 (3)0.4839 (3)0.04888
C320.2048 (2)0.6679 (3)0.5755 (3)0.04888
H330.3063 (10)0.5766 (11)0.5580 (9)0.05866
H340.1012 (9)0.4767 (11)0.2532 (9)0.05866
C350.1692 (3)0.5179 (2)0.1486 (3)0.04888
C360.3206 (2)0.5043 (2)0.2040 (3)0.04888
H370.3644 (9)0.4556 (10)0.3453 (9)0.05866
C380.5854 (3)0.1586 (3)0.6240 (3)0.04888
H390.5602 (10)0.2768 (10)0.7286 (10)0.05866
H400.5691 (10)0.3300 (10)0.6214 (9)0.05866
H410.5749 (9)0.0854 (11)0.4792 (9)0.05866
H420.5805 (9)0.2143 (10)0.4729 (10)0.05866
H430.1879 (9)0.2316 (10)0.6424 (10)0.05866
H440.2231 (10)0.3397 (11)0.6053 (10)0.05866
H450.1276 (10)0.3361 (11)0.6207 (10)0.05866
H460.0515 (12)0.1831 (10)0.3844 (11)0.05866
H470.0159 (12)0.2301 (10)0.4805 (12)0.05866
H480.0736 (10)0.1218 (10)0.4938 (11)0.05866
H490.0032 (12)0.6219 (10)0.4675 (10)0.05866
C500.1153 (2)0.6821 (3)0.5487 (3)0.04888
H510.2383 (10)0.7161 (10)0.6189 (9)0.05866
H520.1203 (9)0.5341 (12)0.0966 (9)0.05866
C530.2511 (3)0.5283 (2)0.1300 (3)0.04888
H540.3734 (9)0.5102 (11)0.1903 (9)0.05866
O550.5512 (4)0.0644 (4)0.6587 (4)0.04888
C560.6768 (2)0.1397 (3)0.6465 (2)0.04888
H570.0887 (10)0.7408 (10)0.5742 (11)0.05866
H580.2582 (8)0.5519 (11)0.0640 (9)0.05866
H590.5553 (11)0.0696 (11)0.7250 (8)0.05866
C600.7329 (2)0.2172 (3)0.6458 (2)0.04888
C610.7070 (3)0.0395 (3)0.6663 (2)0.04888
H620.7126 (10)0.2888 (10)0.6318 (9)0.05866
C630.8182 (2)0.1967 (3)0.6647 (2)0.04888
C640.7908 (2)0.0153 (3)0.6852 (2)0.04888
H650.6700 (10)0.0166 (10)0.6674 (9)0.05866
H660.8563 (9)0.2547 (10)0.6644 (10)0.05866
C670.8503 (2)0.0952 (4)0.6848 (2)0.04888
H680.8068 (10)0.0569 (11)0.6982 (10)0.05866
Cl690.9605 (3)0.0747 (4)0.7061 (3)0.09537
Geometric parameters (Å, º) top
Cl69—C671.824 (6)C61—C641.404 (6)
O16—C101.257 (7)C63—C671.371 (5)
O55—C381.415 (7)C64—C671.403 (5)
O55—H590.867 (12)C2—H40.997 (14)
N7—C141.502 (5)C2—H50.991 (12)
N7—C151.509 (5)C3—H80.993 (15)
N7—C31.486 (6)C3—H90.999 (12)
N17—C281.489 (6)C14—H231.006 (13)
N17—C291.539 (7)C14—H241.000 (14)
N17—C101.394 (7)C15—H250.974 (12)
N7—H130.952 (16)C15—H260.999 (14)
C2—C61.559 (6)C18—H300.971 (14)
C2—C31.533 (5)C19—H331.002 (17)
C6—C101.628 (7)C20—H341.012 (16)
C6—C111.524 (6)C21—H370.966 (14)
C6—C121.548 (6)C22—H390.989 (14)
C11—C181.493 (5)C22—H401.006 (14)
C11—C191.435 (5)C27—H410.990 (14)
C12—C211.415 (7)C27—H420.998 (14)
C12—C201.506 (6)C28—H430.975 (13)
C14—C221.579 (6)C28—H440.994 (17)
C15—C271.568 (6)C28—H451.000 (17)
C18—C311.381 (5)C29—H460.995 (15)
C19—C321.375 (5)C29—H471.018 (19)
C20—C351.348 (6)C29—H480.991 (13)
C21—C361.316 (5)C31—H490.98 (2)
C22—C381.574 (6)C32—H510.932 (14)
C27—C381.567 (6)C35—H520.976 (14)
C31—C501.405 (5)C36—H540.939 (15)
C32—C501.476 (5)C50—H570.948 (15)
C35—C531.444 (7)C53—H580.950 (13)
C36—C531.391 (6)C60—H620.954 (13)
C38—C561.514 (6)C61—H650.932 (15)
C56—C611.345 (5)C63—H660.960 (14)
C56—C601.343 (5)C64—H680.939 (14)
C60—C631.419 (5)
C38—O55—H59108.2 (11)C2—C3—H8110.6 (9)
C3—N7—C15114.0 (3)C2—C3—H9109.1 (8)
C14—N7—C15105.8 (3)H8—C3—H9107.0 (12)
C3—N7—C14115.0 (4)N7—C14—H23107.7 (7)
C10—N17—C28120.3 (4)N7—C14—H24108.5 (8)
C28—N17—C29119.3 (4)C22—C14—H23110.6 (9)
C10—N17—C29120.0 (4)C22—C14—H24113.3 (9)
C14—N7—H13110.0 (9)H23—C14—H24107.8 (12)
C3—N7—H13106.2 (11)N7—C15—H25108.5 (9)
C15—N7—H13105.5 (10)N7—C15—H26109.1 (9)
C3—C2—C6104.1 (3)C27—C15—H25111.7 (11)
N7—C3—C2108.5 (3)C27—C15—H26111.1 (9)
C10—C6—C11118.1 (4)H25—C15—H26107.6 (12)
C11—C6—C12102.3 (3)C11—C18—H30122.0 (9)
C2—C6—C11110.9 (3)C31—C18—H30117.2 (9)
C10—C6—C12106.2 (3)C11—C19—H33125.2 (8)
C2—C6—C10109.8 (3)C32—C19—H33122.3 (8)
C2—C6—C12108.8 (4)C12—C20—H34126.2 (8)
O16—C10—N17116.7 (6)C35—C20—H34117.4 (8)
O16—C10—C6120.1 (5)C12—C21—H37123.4 (9)
N17—C10—C6120.5 (4)C36—C21—H37117.4 (9)
C6—C11—C18119.2 (3)C14—C22—H39109.7 (11)
C18—C11—C19124.4 (3)C14—C22—H40111.5 (9)
C6—C11—C19116.4 (3)C38—C22—H39108.9 (9)
C6—C12—C20120.3 (4)C38—C22—H40110.0 (9)
C6—C12—C21117.9 (4)H39—C22—H40106.2 (11)
C20—C12—C21121.8 (4)C15—C27—H41108.6 (9)
N7—C14—C22108.8 (3)C15—C27—H42110.1 (9)
N7—C15—C27108.9 (3)C38—C27—H41107.7 (8)
C11—C18—C31120.8 (3)C38—C27—H42107.7 (8)
C11—C19—C32112.5 (3)H41—C27—H42107.4 (12)
C12—C20—C35116.4 (4)N17—C28—H43110.3 (8)
C12—C21—C36119.2 (4)N17—C28—H44110.0 (8)
C14—C22—C38110.4 (3)N17—C28—H45107.2 (9)
C15—C27—C38115.1 (4)H43—C28—H44106.6 (13)
C18—C31—C50115.1 (3)H43—C28—H45111.1 (12)
C19—C32—C50123.6 (3)H44—C28—H45111.7 (12)
C20—C35—C53118.8 (4)N17—C29—H46109.5 (11)
C21—C36—C53120.6 (4)N17—C29—H47112.6 (9)
O55—C38—C27102.9 (4)N17—C29—H48110.4 (10)
O55—C38—C56105.5 (4)H46—C29—H47106.7 (15)
O55—C38—C22113.7 (4)H46—C29—H48108.1 (11)
C27—C38—C56107.8 (3)H47—C29—H48109.4 (13)
C22—C38—C27102.2 (3)C18—C31—H49122.7 (8)
C22—C38—C56122.9 (3)C50—C31—H49122.1 (8)
C31—C50—C32123.5 (3)C19—C32—H51114.7 (10)
C35—C53—C36123.2 (3)C50—C32—H51121.7 (10)
C38—C56—C61120.3 (4)C20—C35—H52117.9 (9)
C60—C56—C61115.2 (4)C53—C35—H52123.3 (9)
C38—C56—C60124.5 (3)C21—C36—H54117.3 (8)
C56—C60—C63123.3 (3)C53—C36—H54122.1 (8)
C56—C61—C64123.6 (4)C31—C50—H57114.5 (10)
C60—C63—C67122.5 (3)C32—C50—H57122.1 (10)
C61—C64—C67122.1 (3)C35—C53—H58118.8 (9)
Cl69—C67—C64126.6 (3)C36—C53—H58118.0 (9)
C63—C67—C64113.4 (3)C56—C60—H62116.4 (10)
Cl69—C67—C63120.1 (3)C63—C60—H62120.4 (10)
C3—C2—H4112.6 (8)C56—C61—H65117.8 (10)
C3—C2—H5110.6 (9)C64—C61—H65118.6 (10)
C6—C2—H4110.2 (9)C60—C63—H66120.6 (9)
C6—C2—H5111.7 (10)C67—C63—H66116.9 (9)
H4—C2—H5107.7 (12)C61—C64—H68118.2 (11)
N7—C3—H8110.9 (9)C67—C64—H68119.7 (11)
N7—C3—H9110.7 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N7—H13···Cl10.952 (16)2.278 (16)3.212 (6)166.7 (12)
O55—H59···Cl10.867 (12)2.221 (12)3.069 (7)165.9 (17)
(II) 6-O-Methylerythromycin A top
Crystal data top
C38H69NO13F(000) = 1632.0
Mr = 747.94Dx = 1.163 Mg m3
Orthorhombic, P212121Cu Kα1 radiation, λ = 1.54056 Å
a = 20.1492 (4) ŵ = 0.71 mm1
b = 23.9545 (5) ÅT = 298 K
c = 8.8534 (2) Åcolourless
V = 4273.25 (16) Å3cylinder, 10 × 0.7 mm
Z = 4
Data collection top
STOE Stadi-P
diffractometer
Data collection mode: transmission
Radiation source: sealed x-ray tubeScan method: step
Primary focussing Ge 111 monochromator2θmin = 2.000°, 2θmax = 69.000°, 2θstep = 0.01°
Specimen mounting: glass capillary
Refinement top
Least-squares matrix: full with fixed elements per cycle406 parameters
Rp = 0.021359 restraints
Rwp = 0.0280 constraints
Rexp = 0.018All H-atom parameters refined
RBragg = 0.008Weighting scheme based on measured s.u.'s
χ2 = 2.356(Δ/σ)max = 0.001
6800 data pointsBackground function: Chebyshev with 20 terms
Profile function: modified Thompson-Cox-Hastings pseudo-VoigtPreferred orientation correction: none
Crystal data top
C38H69NO13V = 4273.25 (16) Å3
Mr = 747.94Z = 4
Orthorhombic, P212121Cu Kα1 radiation, λ = 1.54056 Å
a = 20.1492 (4) ŵ = 0.71 mm1
b = 23.9545 (5) ÅT = 298 K
c = 8.8534 (2) Åcylinder, 10 × 0.7 mm
Data collection top
STOE Stadi-P
diffractometer
Scan method: step
Specimen mounting: glass capillary2θmin = 2.000°, 2θmax = 69.000°, 2θstep = 0.01°
Data collection mode: transmission
Refinement top
Rp = 0.0216800 data points
Rwp = 0.028406 parameters
Rexp = 0.018359 restraints
RBragg = 0.008All H-atom parameters refined
χ2 = 2.356
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.0204 (3)0.2325 (2)0.4553 (7)0.03362
C20.0049 (3)0.2932 (2)0.4836 (6)0.03362
C30.0073 (3)0.3256 (2)0.3327 (6)0.03362
C40.0763 (2)0.3560 (2)0.3220 (6)0.03362
C50.0965 (3)0.3716 (2)0.1597 (6)0.03362
C60.1307 (3)0.3232 (2)0.0647 (6)0.03362
C70.2008 (2)0.3173 (2)0.1189 (5)0.03362
C80.2439 (3)0.2743 (2)0.0360 (6)0.03362
C90.2310 (4)0.2128 (2)0.0764 (6)0.03362
C100.2394 (2)0.1920 (2)0.2404 (6)0.03362
C110.1718 (2)0.1794 (2)0.3190 (6)0.03362
C120.1732 (3)0.1685 (2)0.4879 (6)0.03362
C130.1014 (3)0.1648 (2)0.5389 (6)0.03362
C140.0960 (3)0.1403 (2)0.6996 (5)0.03362
C150.0271 (2)0.1346 (2)0.7615 (5)0.03362
C160.0609 (3)0.2952 (2)0.5558 (5)0.03362
C170.0809 (3)0.40502 (19)0.4365 (6)0.03362
C180.1341 (2)0.33538 (19)0.1041 (6)0.03362
C190.3134 (3)0.29367 (19)0.0692 (5)0.03362
C200.2853 (2)0.14103 (19)0.2347 (6)0.03362
C210.2080 (3)0.2130 (2)0.5814 (6)0.03362
C220.0461 (2)0.2504 (2)0.0183 (6)0.03362
O10.0044 (4)0.2064 (3)0.3396 (8)0.03362
O20.0489 (3)0.3670 (3)0.3338 (7)0.03362
O30.1425 (3)0.4188 (2)0.1669 (8)0.03362
O40.1005 (3)0.2711 (2)0.1052 (7)0.03362
O50.2020 (4)0.1842 (3)0.0175 (8)0.03362
O60.1393 (4)0.1337 (3)0.2461 (7)0.03362
O70.2031 (3)0.1166 (2)0.5188 (9)0.03362
O80.0747 (3)0.2212 (2)0.5419 (9)0.03362
C230.1240 (3)0.4700 (2)0.1039 (6)0.03362
C240.1753 (3)0.5117 (2)0.1529 (5)0.03362
C250.1546 (3)0.5671 (2)0.0856 (6)0.03362
C260.1548 (3)0.5623 (2)0.0828 (6)0.03362
C270.1036 (3)0.5192 (2)0.1281 (6)0.03362
C280.1050 (2)0.5096 (2)0.2958 (6)0.03362
C290.1660 (2)0.66466 (19)0.1489 (6)0.03362
C300.2616 (3)0.61278 (19)0.0901 (5)0.03362
N10.1959 (3)0.6102 (2)0.1543 (8)0.03362
O90.1756 (4)0.5156 (2)0.3127 (6)0.03362
O100.1202 (4)0.4664 (2)0.0536 (6)0.03362
C310.1006 (3)0.3637 (2)0.2216 (6)0.03362
C320.1579 (2)0.3996 (2)0.2698 (6)0.03362
C330.1501 (2)0.4621 (2)0.2488 (6)0.03362
C340.1307 (3)0.4708 (2)0.0845 (6)0.03362
C350.0717 (3)0.4337 (2)0.0345 (6)0.03362
C360.0587 (3)0.4301 (2)0.1353 (6)0.03362
C370.2198 (2)0.4875 (2)0.2756 (5)0.03362
C380.1016 (3)0.4861 (2)0.4996 (6)0.03362
O110.0965 (3)0.4866 (3)0.3386 (6)0.03362
O120.1105 (3)0.5272 (2)0.0562 (7)0.03362
O130.0782 (3)0.3767 (2)0.0749 (7)0.03362
H10.0398 (8)0.3095 (8)0.560 (2)0.04034
H20.0005 (10)0.2973 (8)0.252 (2)0.04034
H30.1081 (9)0.3293 (8)0.353 (2)0.04034
H40.0587 (8)0.3812 (9)0.098 (2)0.04034
H50.2057 (8)0.3093 (7)0.241 (2)0.04034
H60.2207 (8)0.3538 (8)0.113 (2)0.04034
H70.2319 (8)0.2779 (8)0.069 (2)0.04034
H80.2569 (8)0.2226 (7)0.301 (2)0.04034
H90.1453 (10)0.2097 (8)0.310 (2)0.04034
H100.0772 (8)0.1431 (8)0.463 (2)0.04034
H110.1143 (9)0.1011 (8)0.693 (2)0.04034
H120.1188 (10)0.1650 (8)0.768 (3)0.04034
H130.0016 (10)0.1217 (9)0.6845 (19)0.04034
H140.0118 (10)0.1684 (9)0.815 (2)0.04034
H150.0239 (10)0.1146 (9)0.8455 (19)0.04034
H160.0691 (8)0.2606 (7)0.607 (2)0.04034
H170.0944 (9)0.2943 (7)0.472 (2)0.04034
H180.0696 (8)0.3271 (8)0.621 (2)0.04034
H190.0661 (8)0.3956 (9)0.535 (2)0.04034
H200.1260 (9)0.4184 (9)0.453 (2)0.04034
H210.0549 (8)0.4393 (9)0.400 (2)0.04034
H220.1627 (9)0.3103 (8)0.147 (2)0.04034
H230.0904 (9)0.3326 (8)0.143 (2)0.04034
H240.1436 (9)0.3750 (8)0.124 (2)0.04034
H250.3142 (9)0.3298 (8)0.034 (2)0.04034
H260.3427 (9)0.2688 (8)0.001 (2)0.04034
H270.3274 (9)0.2878 (8)0.190 (2)0.04034
H280.2618 (7)0.1093 (8)0.178 (2)0.04034
H290.2940 (8)0.1331 (8)0.332 (2)0.04034
H300.3309 (9)0.1525 (8)0.202 (2)0.04034
H310.1968 (8)0.2119 (8)0.690 (2)0.04034
H320.2024 (8)0.2493 (7)0.539 (2)0.04034
H330.2545 (9)0.2063 (8)0.574 (2)0.04034
H340.0221 (9)0.2252 (7)0.096 (2)0.04034
H350.0581 (8)0.2346 (8)0.068 (2)0.04034
H360.0141 (9)0.2815 (8)0.008 (2)0.04034
H370.1376 (11)0.1433 (8)0.151 (2)0.04034
H380.1735 (8)0.0939 (7)0.518 (4)0.04034
H390.0809 (8)0.4827 (7)0.145 (2)0.04034
H400.2261 (9)0.4981 (7)0.120 (3)0.04034
H410.1097 (9)0.5741 (9)0.116 (2)0.04034
H420.1462 (10)0.5961 (8)0.134 (2)0.04034
H430.2032 (9)0.5529 (9)0.121 (2)0.04034
H440.0556 (8)0.5310 (7)0.099 (2)0.04034
H450.1525 (10)0.5010 (7)0.332 (2)0.04034
H460.0783 (8)0.4782 (7)0.319 (2)0.04034
H470.0828 (8)0.5439 (8)0.350 (2)0.04034
H480.1201 (9)0.6612 (8)0.150 (2)0.04034
H490.1805 (9)0.6900 (8)0.237 (2)0.04034
H500.1824 (8)0.6860 (8)0.044 (2)0.04034
H510.2932 (8)0.6243 (8)0.1704 (19)0.04034
H520.2758 (8)0.5760 (8)0.060 (2)0.04034
H530.2621 (8)0.6391 (7)0.000 (2)0.04034
H540.1726 (15)0.5488 (8)0.336 (2)0.04034
H550.1165 (9)0.3240 (8)0.209 (2)0.04034
H560.1983 (9)0.3889 (8)0.208 (2)0.04034
H570.1721 (9)0.3941 (7)0.375 (2)0.04034
H580.1717 (9)0.4640 (7)0.018 (2)0.04034
H590.0319 (9)0.4473 (9)0.0846 (19)0.04034
H600.0684 (8)0.4630 (8)0.176 (2)0.04034
H610.0815 (9)0.4004 (9)0.175 (2)0.04034
H620.0142 (10)0.4148 (9)0.1555 (19)0.04034
H630.2499 (9)0.4655 (8)0.211 (3)0.04034
H640.2305 (9)0.4866 (7)0.402 (3)0.04034
H650.2210 (9)0.5258 (7)0.255 (2)0.04034
H660.0533 (8)0.5015 (7)0.535 (2)0.04034
H670.1125 (9)0.4530 (8)0.536 (2)0.04034
H680.1262 (10)0.5151 (7)0.549 (2)0.04034
H690.0865 (11)0.5352 (7)0.140 (2)0.04034
Geometric parameters (Å, º) top
O1—C11.243 (9)C7—H51.102 (18)
O2—C31.505 (9)C7—H60.963 (19)
O2—C311.442 (8)C8—H70.964 (18)
O3—C51.463 (8)C10—H80.974 (18)
O3—C231.398 (7)C11—H90.91 (2)
O4—C61.434 (7)C13—H100.980 (18)
O4—C221.428 (7)C14—H111.01 (2)
O5—C91.226 (9)C14—H120.96 (2)
O6—C111.430 (8)C15—H130.946 (19)
O7—C121.408 (7)C15—H140.99 (2)
O8—C11.363 (9)C15—H150.887 (19)
O8—C131.455 (7)C16—H160.959 (18)
O9—C241.418 (7)C16—H171.003 (19)
O10—C231.399 (8)C16—H180.974 (19)
O10—C271.465 (7)C17—H190.949 (18)
O11—C331.464 (8)C17—H200.98 (2)
O11—C381.429 (8)C17—H211.03 (2)
O12—C341.433 (7)C18—H220.915 (19)
O13—C311.410 (8)C18—H230.948 (18)
O13—C351.418 (7)C18—H240.98 (2)
O6—H370.874 (19)C19—H250.92 (2)
O7—H380.807 (17)C19—H261.044 (19)
O9—H540.82 (2)C19—H271.115 (18)
O12—H690.91 (2)C20—H281.027 (18)
N1—C291.438 (7)C20—H290.899 (18)
N1—C301.442 (9)C20—H301.002 (19)
N1—C251.459 (8)C21—H310.988 (18)
C1—C21.508 (7)C21—H320.954 (18)
C2—C161.473 (8)C21—H330.953 (19)
C2—C31.546 (7)C22—H341.035 (18)
C3—C41.572 (7)C22—H350.886 (18)
C4—C171.554 (7)C22—H361.012 (19)
C4—C51.540 (7)C23—H390.990 (17)
C5—C61.590 (7)C24—H401.11 (2)
C6—C71.498 (7)C25—H410.959 (19)
C6—C181.524 (7)C26—H420.944 (19)
C7—C81.534 (7)C26—H431.057 (19)
C8—C91.538 (7)C27—H441.040 (17)
C8—C191.504 (8)C28—H451.03 (2)
C9—C101.544 (7)C28—H460.947 (17)
C10—C201.533 (6)C28—H471.051 (19)
C10—C111.559 (6)C29—H480.929 (19)
C11—C121.518 (7)C29—H491.031 (19)
C12—C131.518 (8)C29—H501.110 (19)
C12—C211.521 (7)C30—H510.994 (18)
C13—C141.543 (6)C30—H520.964 (19)
C14—C151.499 (7)C30—H531.017 (18)
C23—C241.502 (8)C31—H551.01 (2)
C24—C251.513 (7)C32—H561.014 (18)
C25—C261.495 (8)C32—H570.983 (18)
C26—C271.514 (8)C34—H581.027 (19)
C27—C281.503 (7)C35—H590.973 (19)
C31—C321.502 (7)C36—H600.888 (19)
C32—C331.517 (7)C36—H610.92 (2)
C33—C371.549 (6)C36—H620.99 (2)
C33—C341.521 (7)C37—H630.986 (19)
C34—C351.549 (8)C37—H641.14 (3)
C35—C361.528 (8)C37—H650.936 (17)
C2—H11.051 (18)C38—H661.087 (17)
C3—H20.994 (19)C38—H670.88 (2)
C4—H30.946 (19)C38—H680.959 (19)
C5—H40.965 (18)
C3—O2—C31120.2 (5)C15—C14—H11105.9 (11)
C5—O3—C23119.4 (5)C15—C14—H12105.5 (12)
C6—O4—C22119.6 (5)H11—C14—H12115.7 (16)
C1—O8—C13118.1 (5)C14—C15—H13109.4 (12)
C23—O10—C27114.1 (4)C14—C15—H14113.0 (12)
C33—O11—C38119.0 (5)C14—C15—H15115.0 (14)
C31—O13—C35118.4 (5)H13—C15—H14115.0 (18)
C11—O6—H37104.6 (14)H13—C15—H15112.5 (18)
C12—O7—H38106.1 (14)H14—C15—H1591.0 (18)
C24—O9—H54108.3 (13)C2—C16—H16109.4 (11)
C34—O12—H69102.0 (12)C2—C16—H17106.5 (11)
C29—N1—C30109.4 (4)C2—C16—H18116.4 (11)
C25—N1—C29112.9 (5)H16—C16—H17102.4 (15)
C25—N1—C30112.9 (5)H16—C16—H18111.5 (15)
O1—C1—C2124.6 (6)H17—C16—H18109.5 (15)
O8—C1—C2105.3 (5)C4—C17—H19113.7 (13)
O1—C1—O8124.9 (6)C4—C17—H20113.7 (12)
C1—C2—C3109.5 (4)C4—C17—H21111.6 (11)
C1—C2—C16106.9 (4)H19—C17—H20103.5 (15)
C3—C2—C16112.8 (5)H19—C17—H21108.6 (16)
O2—C3—C4111.1 (4)H20—C17—H21105.1 (16)
C2—C3—C4108.2 (4)C6—C18—H22108.0 (12)
O2—C3—C2107.6 (5)C6—C18—H23107.5 (12)
C3—C4—C5113.7 (4)C6—C18—H24111.7 (11)
C5—C4—C17114.2 (4)H22—C18—H23112.8 (17)
C3—C4—C17111.3 (4)H22—C18—H24115.9 (16)
O3—C5—C6108.2 (5)H23—C18—H24100.6 (16)
O3—C5—C4108.3 (5)C8—C19—H25103.9 (12)
C4—C5—C6115.6 (4)C8—C19—H26103.5 (11)
O4—C6—C7103.8 (4)C8—C19—H27112.6 (10)
O4—C6—C18115.5 (5)H25—C19—H26109.0 (16)
C5—C6—C7107.9 (4)H25—C19—H27116.1 (16)
C5—C6—C18113.5 (4)H26—C19—H27110.9 (15)
O4—C6—C5108.6 (5)C10—C20—H28109.1 (10)
C7—C6—C18106.8 (4)C10—C20—H29104.7 (12)
C6—C7—C8116.3 (4)C10—C20—H30110.2 (12)
C7—C8—C9115.9 (5)H28—C20—H29113.7 (16)
C9—C8—C19114.0 (5)H28—C20—H30119.0 (14)
C7—C8—C19103.1 (4)H29—C20—H3099.0 (15)
O5—C9—C8117.3 (6)C12—C21—H31113.9 (11)
O5—C9—C10120.6 (5)C12—C21—H32111.7 (11)
C8—C9—C10120.6 (4)C12—C21—H33107.3 (12)
C11—C10—C20112.8 (4)H31—C21—H32112.4 (16)
C9—C10—C11112.7 (4)H31—C21—H33106.7 (15)
C9—C10—C20107.0 (4)H32—C21—H33104.1 (16)
O6—C11—C12108.8 (4)O4—C22—H34101.7 (11)
C10—C11—C12117.2 (4)O4—C22—H35113.8 (11)
O6—C11—C10110.3 (4)O4—C22—H36110.9 (11)
O7—C12—C11110.6 (5)H34—C22—H35116.8 (16)
C13—C12—C21108.6 (4)H34—C22—H36106.5 (15)
O7—C12—C21108.4 (5)H35—C22—H36106.8 (16)
C11—C12—C13106.6 (4)O3—C23—H39110.9 (11)
O7—C12—C13107.4 (5)O10—C23—H39109.7 (12)
C11—C12—C21115.1 (4)C24—C23—H39107.1 (11)
O8—C13—C12107.7 (4)O9—C24—H40106.1 (14)
O8—C13—C14108.1 (5)C23—C24—H40111.3 (11)
C12—C13—C14111.3 (5)C25—C24—H40114.0 (11)
C13—C14—C15115.9 (5)N1—C25—H41107.3 (13)
O3—C23—C24106.6 (5)C24—C25—H41107.6 (13)
O10—C23—C24111.5 (5)C26—C25—H41107.2 (12)
O3—C23—O10111.0 (5)C25—C26—H42114.4 (12)
O9—C24—C25109.7 (4)C25—C26—H43109.8 (11)
C23—C24—C25106.3 (4)C27—C26—H42109.4 (13)
O9—C24—C23109.6 (5)C27—C26—H43113.5 (12)
N1—C25—C24107.4 (5)H42—C26—H43101.5 (17)
N1—C25—C26117.9 (5)O10—C27—H44109.6 (11)
C24—C25—C26108.9 (4)C26—C27—H44112.5 (10)
C25—C26—C27108.4 (4)C28—C27—H44107.7 (11)
O10—C27—C28108.0 (4)C27—C28—H45110.8 (11)
C26—C27—C28110.7 (4)C27—C28—H46109.0 (12)
O10—C27—C26108.3 (5)C27—C28—H47108.9 (11)
O2—C31—O13113.0 (5)H45—C28—H46107.5 (15)
O2—C31—C32109.2 (5)H45—C28—H47114.2 (14)
O13—C31—C32112.4 (5)H46—C28—H47106.3 (15)
C31—C32—C33116.8 (4)N1—C29—H48109.6 (13)
O11—C33—C34106.0 (4)N1—C29—H49113.0 (11)
O11—C33—C37115.4 (4)N1—C29—H50108.7 (10)
C32—C33—C34106.2 (4)H48—C29—H49109.1 (16)
C32—C33—C37106.0 (3)H48—C29—H50110.3 (15)
O11—C33—C32113.9 (4)H49—C29—H50106.1 (14)
C34—C33—C37109.0 (4)N1—C30—H51108.6 (10)
O12—C34—C33111.7 (4)N1—C30—H52110.0 (11)
O12—C34—C35105.8 (5)N1—C30—H53110.2 (10)
C33—C34—C35113.1 (4)H51—C30—H52105.2 (15)
O13—C35—C36102.1 (4)H51—C30—H53112.5 (15)
C34—C35—C36116.4 (4)H52—C30—H53110.3 (15)
O13—C35—C34114.2 (5)O2—C31—H55110.9 (11)
C1—C2—H1109.1 (11)O13—C31—H55102.0 (11)
C3—C2—H1110.4 (11)C32—C31—H55109.1 (12)
C16—C2—H1108.1 (10)C31—C32—H56108.6 (11)
O2—C3—H2110.5 (13)C31—C32—H57114.6 (11)
C2—C3—H2105.9 (12)C33—C32—H56105.5 (12)
C4—C3—H2113.2 (12)C33—C32—H57106.2 (11)
C3—C4—H3105.6 (12)H56—C32—H57104.1 (15)
C5—C4—H3104.8 (12)O12—C34—H58106.1 (11)
C17—C4—H3106.3 (12)C33—C34—H58108.7 (11)
O3—C5—H4109.9 (13)C35—C34—H58111.3 (11)
C4—C5—H4112.2 (11)O13—C35—H59106.5 (13)
C6—C5—H4102.5 (12)C34—C35—H59108.1 (12)
C6—C7—H5114.5 (9)C36—C35—H59109.0 (11)
C6—C7—H6106.8 (11)C35—C36—H60108.1 (12)
C8—C7—H5107.6 (9)C35—C36—H61109.6 (12)
C8—C7—H6110.4 (11)C35—C36—H62110.8 (11)
H5—C7—H6100.0 (14)H60—C36—H61115.0 (18)
C7—C8—H7105.0 (12)H60—C36—H62117.2 (17)
C9—C8—H7105.5 (12)H61—C36—H6295.6 (18)
C19—C8—H7113.2 (11)C33—C37—H63105.0 (11)
C9—C10—H8108.3 (11)C33—C37—H64108.3 (10)
C11—C10—H8102.5 (11)C33—C37—H65112.3 (12)
C20—C10—H8113.5 (10)H63—C37—H64116.3 (14)
O6—C11—H9107.7 (13)H63—C37—H65113.3 (16)
C10—C11—H9108.7 (13)H64—C37—H65101.8 (14)
C12—C11—H9103.6 (12)O11—C38—H66102.7 (10)
O8—C13—H10108.7 (12)O11—C38—H67112.9 (13)
C12—C13—H10107.5 (11)O11—C38—H68119.1 (12)
C14—C13—H10113.3 (12)H66—C38—H67115.0 (16)
C13—C14—H11105.9 (11)H66—C38—H6894.9 (15)
C13—C14—H12108.2 (12)H67—C38—H68110.8 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H37···O50.874 (19)2.21 (2)2.917 (10)138.2 (19)
O7—H38···O120.807 (17)2.14 (2)2.917 (8)161 (3)
O9—H54···N10.82 (2)2.23 (2)2.696 (7)116.2 (16)
O12—H69···O110.91 (2)2.118 (18)2.698 (8)120.8 (16)

Experimental details

(I)(II)
Crystal data
Chemical formulaC29H34ClN2O2+·ClC38H69NO13
Mr513.48747.94
Crystal system, space groupMonoclinic, P21/cOrthorhombic, P212121
Temperature (K)298298
a, b, c (Å)16.7095 (8), 12.3773 (5), 13.2135 (5)20.1492 (4), 23.9545 (5), 8.8534 (2)
α, β, γ (°)90, 101.642 (3), 9090, 90, 90
V3)2676.59 (19)4273.25 (16)
Z44
Radiation typeCu Kα1, λ = 1.54056 ÅCu Kα1, λ = 1.54056 Å
µ (mm1)2.400.71
Specimen shape, size (mm)Cylinder, 10 × 1Cylinder, 10 × 0.7
Data collection
DiffractometerSTOE Stadi-P
diffractometer
STOE Stadi-P
diffractometer
Specimen mountingGlass capillaryGlass capillary
Data collection modeTransmissionTransmission
Scan methodStepStep
2θ values (°)2θmin = 2.000 2θmax = 100.190 2θstep = 0.012θmin = 2.000 2θmax = 69.000 2θstep = 0.01
Refinement
R factors and goodness of fitRp = 0.043, Rwp = 0.060, Rexp = 0.027, RBragg = 0.030, χ2 = 5.081Rp = 0.021, Rwp = 0.028, Rexp = 0.018, RBragg = 0.008, χ2 = 2.356
No. of data points98206800
No. of parameters259406
No. of restraints201359
H-atom treatmentAll H-atom parameters refinedAll H-atom parameters refined

Computer programs: STOE WinXPOW (STOE & Cie GmbH, 2006), TOPAS Academic (Coelho, 2007), FIDEL (Habermehl et al., 2014).

 

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