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Crystal structure determination is the key to a detailed understanding of crystalline materials and their properties. This requires either single crystals or high-quality single-phase powder X-ray diffraction data. The present contribution demonstrates a novel method to reconstruct single-phase powder diffraction data from diffraction patterns of mixtures of several components and subsequently to determine the individual crystal structures. The new method does not require recourse to any database of known materials but relies purely on numerical separation of the mixture data into individual component diffractograms. The resulting diffractograms can subsequently be treated like single-phase powder diffraction data, i.e. indexing, structure solution and Rietveld refinement. This development opens up a host of new opportunities in materials science and related areas. For example, crystal structures can now be determined at much earlier stages when only impure samples or polymorphic mixtures are available.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600576714003379/to5064sup1.cif
Contains datablocks global, Al2O3_BTEM, CaF2_BTEM, ZnO_BTEM, Tolbutamide_IL, Tolbutamide_II, Tolbutamide_III, Glycine, paracetamol, Lactose_monohydrate

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S1600576714003379/to5064sup2.pdf
Supplementary figures

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600576714003379/to5064Al2O3_BTEMsup3.hkl
Contains datablock Al2O3_BTEM

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600576714003379/to5064CaF2_BTEMsup4.hkl
Contains datablock CaF2_BTEM

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600576714003379/to5064Glycinesup5.hkl
Contains datablock Glycine

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600576714003379/to5064Lactose_monohydratesup6.hkl
Contains datablock Lactose_monohydrate

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600576714003379/to5064Tolbutamide_IIsup7.hkl
Contains datablock Tolbutamide_II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600576714003379/to5064Tolbutamide_IIIsup8.hkl
Contains datablock Tolbutamide_III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600576714003379/to5064Tolbutamide_ILsup9.hkl
Contains datablock Tolbutamide_IL

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600576714003379/to5064ZnO_BTEMsup10.hkl
Contains datablock ZnO_BTEM

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600576714003379/to5064paracetamolsup11.hkl
Contains datablock Paracetamol

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S1600576714003379/to5064CaF2_BTEMsup12.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S1600576714003379/to5064Tolbutamide_ILsup13.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S1600576714003379/to5064Tolbutamide_IIsup14.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S1600576714003379/to5064Tolbutamide_IIIsup15.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S1600576714003379/to5064Glycinesup16.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S1600576714003379/to5064paracetamolsup17.cml
Supplementary material

CCDC references: 986780; 986781; 986782; 986783; 986784; 986785; 986786; 986787; 986788

Computing details top

For all compounds, data collection: unknown; cell refinement: Topas v4.2 (Bruker AXS GmbH, 2009); data reduction: Topas v4.2 (Bruker AXS GmbH, 2009). Program(s) used to solve structure: Topas v4.2 (Bruker AXS GmbH, 2009) for Al2O3_BTEM, CaF2_BTEM, ZnO_BTEM, Glycine, paracetamol, Lactose_monohydrate; PowderSolve / Materials Studio (Accelrys) for Tolbutamide_IL, Tolbutamide_II, Tolbutamide_III. For all compounds, program(s) used to refine structure: Topas v4.2 (Bruker AXS GmbH, 2009); molecular graphics: Diamond 3.1f; software used to prepare material for publication: CSD.

(Al2O3_BTEM) aluminium oxide top
Crystal data top
Al2O3F(000) = 300
Mr = 101.96Dx = 3.989 Mg m3
Hexagonal, R3cCu Kα radiation, λ = 1.541802 Å
a = 4.75815 (4) ÅT = 298 K
c = 12.98970 (18) Åcolourless
V = 254.69 (1) Å3?, ? × ? × ? mm
Z = 6
Data collection top
Philips 3020
diffractometer
Scan method: step
Radiation source: sealed X-ray tube2θmin = 5°, 2θmax = 150°, 2θstep = 0.02°
Diffracted beam Graphite monochromator
Refinement top
Refinement on InetProfile function: fundamental parameter
Least-squares matrix: full with fixed elements per cycle12 parameters
Rp = 0.1180 restraints
Rwp = 0.2360 constraints
Rexp = 0.247Weighting scheme based on measured s.u.'s 1/[Yi + σ(Yi)]
RBragg = 0.018(Δ/σ)max = 0.01
χ2 = 0.009Background function: Chebychev of order 3, plus 1/x
7250 data pointsPreferred orientation correction: none
Excluded region(s): 0
Crystal data top
Al2O3V = 254.69 (1) Å3
Mr = 101.96Z = 6
Hexagonal, R3cCu Kα radiation, λ = 1.541802 Å
a = 4.75815 (4) ÅT = 298 K
c = 12.98970 (18) Å?, ? × ? × ? mm
Data collection top
Philips 3020
diffractometer
2θmin = 5°, 2θmax = 150°, 2θstep = 0.02°
Scan method: step
Refinement top
Rp = 0.118χ2 = 0.009
Rwp = 0.2367250 data points
Rexp = 0.24712 parameters
RBragg = 0.0180 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Al1000.35229 (7)0.0033 (2)
O10.3062 (3)00.250.0021 (4)
Geometric parameters (Å, º) top
Al1—O11.9719 (14)Al1—O1iii1.8537 (9)
Al1—O1i1.9719 (14)Al1—O1iv1.8537 (9)
Al1—O1ii1.9719 (12)Al1—O1v1.8537 (15)
O1—Al1—O1i79.56 (5)O1ii—Al1—O1v86.35 (5)
O1—Al1—O1ii79.56 (6)O1iii—Al1—O1iv101.23 (6)
O1—Al1—O1iii86.35 (4)O1iii—Al1—O1v101.23 (7)
O1—Al1—O1iv90.78 (3)O1iv—Al1—O1v101.23 (6)
O1—Al1—O1v164.13 (7)Al1—O1—Al1vi84.73 (7)
O1i—Al1—O1ii79.56 (6)Al1—O1—Al1iii93.65 (4)
O1i—Al1—O1iii164.13 (7)Al1—O1—Al1vii132.18 (3)
O1i—Al1—O1iv86.35 (4)Al1vi—O1—Al1iii132.18 (3)
O1i—Al1—O1v90.78 (4)Al1vi—O1—Al1vii93.65 (4)
O1ii—Al1—O1iii90.78 (5)Al1iii—O1—Al1vii120.34 (8)
O1ii—Al1—O1iv164.13 (7)
Symmetry codes: (i) y, xy, z; (ii) x+y, x, z; (iii) x+1/3, y1/3, z+2/3; (iv) y+1/3, x+y+2/3, z+2/3; (v) xy2/3, x1/3, z+2/3; (vi) y, x, z+1/2; (vii) y+2/3, x+1/3, z1/6.
(CaF2_BTEM) calcium fluoride top
Crystal data top
CaF2F(000) = 152
Mr = 78.08Dx = 3.181 Mg m3
Cubic, Fm3mCu Kα radiation, λ = 1.541802 Å
a = 5.46321 (5) ÅT = 298 K
V = 163.06 (1) Å3colourless
Z = 4?, ? × ? × ? mm
Data collection top
Philips 3020
diffractometer
Scan method: step
Radiation source: sealed X-ray tube2θmin = 5°, 2θmax = 150°, 2θstep = 0.02°
Graphite Monochromator monochromator
Refinement top
Refinement on InetProfile function: fundamental parameter
Least-squares matrix: full with fixed elements per cycle12 parameters
Rp = 0.1270 restraints
Rwp = 0.2560 constraints
Rexp = 0.387Weighting scheme based on measured s.u.'s 1/[Yi + σ(Yi)]
RBragg = 0.015(Δ/σ)max = 0.01
χ2 = 0.436Background function: Chebychev of order 3, plus 1/x
7250 data pointsPreferred orientation correction: none
Crystal data top
CaF2Z = 4
Mr = 78.08Cu Kα radiation, λ = 1.541802 Å
Cubic, Fm3mT = 298 K
a = 5.46321 (5) Å?, ? × ? × ? mm
V = 163.06 (1) Å3
Data collection top
Philips 3020
diffractometer
2θmin = 5°, 2θmax = 150°, 2θstep = 0.02°
Scan method: step
Refinement top
Rp = 0.127χ2 = 0.436
Rwp = 0.2567250 data points
Rexp = 0.38712 parameters
RBragg = 0.0150 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ca10000.0063 (3)
F10.250.250.250.00783 (5)
Geometric parameters (Å, º) top
Ca1—F12.3656Ca1—F1iv2.3656
Ca1—F1i2.3656Ca1—F1v2.3656
Ca1—F1ii2.3656Ca1—F1vi2.3656
Ca1—F1iii2.3656Ca1—F1vii2.3656
F1—Ca1—F1i109.47F1ii—Ca1—F1vii70.53
F1—Ca1—F1ii109.47F1iii—Ca1—F1iv180.0 (5)
F1—Ca1—F1iii109.47F1iii—Ca1—F1v70.53
F1—Ca1—F1iv70.53F1iii—Ca1—F1vi70.53
F1—Ca1—F1v70.53F1iii—Ca1—F1vii70.53
F1—Ca1—F1vi70.53F1iv—Ca1—F1v109.47
F1—Ca1—F1vii180.0 (5)F1iv—Ca1—F1vi109.47
F1i—Ca1—F1ii109.47F1iv—Ca1—F1vii109.47
F1i—Ca1—F1iii109.47F1v—Ca1—F1vi109.47
F1i—Ca1—F1iv70.53F1v—Ca1—F1vii109.47
F1i—Ca1—F1v70.53F1vi—Ca1—F1vii109.47
F1i—Ca1—F1vi180.0 (5)Ca1—F1—Ca1viii109.47
F1i—Ca1—F1vii70.53Ca1—F1—Ca1ix109.47
F1ii—Ca1—F1iii109.47Ca1—F1—Ca1x109.47
F1ii—Ca1—F1iv70.53Ca1viii—F1—Ca1ix109.47
F1ii—Ca1—F1v180.0 (5)Ca1viii—F1—Ca1x109.47
F1ii—Ca1—F1vi70.53Ca1ix—F1—Ca1x109.47
Symmetry codes: (i) x, y1/2, z1/2; (ii) x1/2, y, z1/2; (iii) x1/2, y1/2, z; (iv) y, x, z; (v) y, x1/2, z+1/2; (vi) y1/2, x, z+1/2; (vii) y1/2, x1/2, z; (viii) x, y+1/2, z+1/2; (ix) x+1/2, y, z+1/2; (x) x+1/2, y+1/2, z.
(ZnO_BTEM) zinc oxide top
Crystal data top
ZnOF(000) = 76
Mr = 81.39Dx = 5.679 Mg m3
Hexagonal, P63mcCu Kα radiation, λ = 1.541802 Å
a = 3.249308 (18) ÅT = 298 K
c = 5.20571 (4) Åcolourless
V = 47.60 (1) Å3?, ? × ? × ? mm
Z = 2
Data collection top
Philips 3020
diffractometer
Scan method: step
Radiation source: sealed X-ray tube2θmin = 5°, 2θmax = 150°, 2θstep = 0.02°
Graphite Monochromator monochromator
Refinement top
Refinement on InetProfile function: fundamental parameter
Least-squares matrix: full with fixed elements per cycle12 parameters
Rp = 0.0790 restraints
Rwp = 0.1490 constraints
Rexp = 0.337Weighting scheme based on measured s.u.'s 1/[Yi + σ(Yi)]
RBragg = 0.018(Δ/σ)max = 0.01
χ2 = 0.194Background function: Chebychev of order 3, plus 1/x
7250 data pointsPreferred orientation correction: none
Excluded region(s): 0
Crystal data top
ZnOV = 47.60 (1) Å3
Mr = 81.39Z = 2
Hexagonal, P63mcCu Kα radiation, λ = 1.541802 Å
a = 3.249308 (18) ÅT = 298 K
c = 5.20571 (4) Å?, ? × ? × ? mm
Data collection top
Philips 3020
diffractometer
2θmin = 5°, 2θmax = 150°, 2θstep = 0.02°
Scan method: step
Refinement top
Rp = 0.079χ2 = 0.194
Rwp = 0.1497250 data points
Rexp = 0.33712 parameters
RBragg = 0.0180 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn0.3333330.6666670.50.00623 (16)
O0.6666670.3333330.3790 (6)0.0058 (8)
Geometric parameters (Å, º) top
Zn—Oi1.9789 (10)Zn—Oii1.9789 (10)
Zn—O1.9789 (10)Zn—Oiii1.973 (3)
Oi—Zn—O110.37 (6)Zniv—O—Zn110.37 (8)
Oi—Zn—Oii110.37 (6)Zniv—O—Znv110.37 (8)
Oi—Zn—Oiii108.56 (9)Zniv—O—Znvi108.56 (9)
O—Zn—Oii110.37 (6)Zn—O—Znv110.37 (8)
O—Zn—Oiii108.56 (9)Zn—O—Znvi108.56 (9)
Oii—Zn—Oiii108.56 (9)Znv—O—Znvi108.56 (9)
Symmetry codes: (i) x1, y, z; (ii) x, y+1, z; (iii) x+1, y+1, z+1/2; (iv) x, y1, z; (v) x+1, y, z; (vi) x+1, y+1, z1/2.
(Tolbutamide_IL) N-[(butylamino)carbonyl]-4-methylbenzenesulfonamide top
Crystal data top
C12H18N2O3SZ = 4
Mr = 270.35F(000) = 576
Orthorhombic, Pna21Dx = 1.237 Mg m3
a = 20.3188 (7) ÅCu Kα radiation, λ = 1.54180 Å
b = 7.84999 (12) ÅT = 298 K
c = 9.1054 (4) Åcolourless
V = 1452.33 (14) Å3?, ? × ? × ? mm
Data collection top
Bruker D8
diffractometer
Scan method: step
Radiation source: sealed X-ray tube2θmin = 5°, 2θmax = 50°, 2θstep = 0.017°
None monochromator
Refinement top
Refinement on Inet22 parameters
Least-squares matrix: full with fixed elements per cycle0 restraints
Rp = 0.0830 constraints
Rwp = 0.122H-atom parameters not refined
Rexp = 0.042Weighting scheme based on measured s.u.'s 1/[Yi + σ(Yi)]
RBragg = 0.054(Δ/σ)max = 0.01
χ2 = 8.294Background function: Chebychev of order 2 + 1/X
2695 data pointsPreferred orientation correction: spherical harmonics order 4
Profile function: fundamental parameter
Crystal data top
C12H18N2O3SV = 1452.33 (14) Å3
Mr = 270.35Z = 4
Orthorhombic, Pna21Cu Kα radiation, λ = 1.54180 Å
a = 20.3188 (7) ÅT = 298 K
b = 7.84999 (12) Å?, ? × ? × ? mm
c = 9.1054 (4) Å
Data collection top
Bruker D8
diffractometer
2θmin = 5°, 2θmax = 50°, 2θstep = 0.017°
Scan method: step
Refinement top
Rp = 0.0832695 data points
Rwp = 0.12222 parameters
Rexp = 0.0420 restraints
RBragg = 0.054H-atom parameters not refined
χ2 = 8.294
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.602193 (16)1.6660 (5)0.301 (9)0.1929 (3)
O10.61777 (15)1.7862 (7)0.418 (10)0.1929 (3)
O20.6121 (2)1.7069 (3)0.147 (9)0.1929 (3)
O30.4899 (2)1.4162 (7)0.477 (8)0.1929 (3)
N10.521163 (1)1.6223 (5)0.316 (9)0.1929 (3)
N20.45944 (12)1.3852 (4)0.237 (8)0.1929 (3)
C10.64441 (3)1.4705 (5)0.339 (9)0.1929 (3)
C20.48833 (4)1.4663 (6)0.351 (8)0.1929 (3)
C30.62642 (8)1.3235 (4)0.263 (9)0.1929 (3)
C40.69403 (18)1.4671 (7)0.445 (10)0.1929 (3)
C50.65854 (4)1.1715 (5)0.295 (9)0.1929 (3)
C60.7255 (2)1.3138 (7)0.475 (10)0.1929 (3)
C70.40986 (4)1.2537 (4)0.262 (8)0.1929 (3)
C80.70819 (11)1.1638 (6)0.401 (10)0.1929 (3)
C90.44859 (19)1.0544 (10)0.266 (11)0.1929 (3)
C100.74164 (16)0.9974 (6)0.437 (10)0.1929 (3)
C110.4059 (9)0.92120 (10)0.221 (10)0.1929 (3)
C120.38262 (9)0.8152 (12)0.353 (10)0.1929 (3)
H10.49198 (8)1.7019 (5)0.258 (9)0.1929 (3)
H20.58887 (19)1.3294 (3)0.179 (9)0.1929 (3)
H30.7084 (3)1.5831 (7)0.500 (10)0.1929 (3)
H40.47583 (16)1.41013 (11)0.135 (8)0.1929 (3)
H50.64504 (12)1.0572 (4)0.235 (9)0.1929 (3)
H60.7645 (3)1.3110 (8)0.556 (10)0.1929 (3)
H70.3923 (12)1.261 (2)0.362 (7)0.1929 (3)
H80.3821 (4)1.2389 (11)0.171 (6)0.1929 (3)
H90.4737 (9)1.038 (3)0.375 (12)0.1929 (3)
H100.4973 (9)1.0577 (11)0.189 (13)0.1929 (3)
H110.7152 (3)0.9302 (8)0.524 (9)0.1929 (3)
H120.7920 (2)1.0175 (7)0.475 (10)0.1929 (3)
H130.74313 (3)0.9131 (5)0.341 (10)0.1929 (3)
H140.3586 (11)0.9863 (11)0.175 (8)0.1929 (3)
H150.4243 (18)0.84846 (17)0.137 (12)0.1929 (3)
H160.3479 (7)0.71629 (14)0.319 (9)0.1929 (3)
H170.3591 (8)0.8902 (16)0.440 (9)0.1929 (3)
H180.42550 (14)0.752 (3)0.401 (12)0.1929 (3)
Geometric parameters (Å, º) top
S1—O11.46 (9)C5—H51.08 (6)
S1—O21.45 (12)C6—C81.40 (6)
S1—N11.687 (10)C6—H61.09 (9)
S1—C11.79 (2)C7—H70.98 (9)
O3—C21.21 (10)C7—H81.01 (7)
N1—C21.43 (2)C8—C101.51 (3)
N2—C21.35 (8)C9—C111.42 (4)
N2—C71.459 (16)C10—H111.09 (9)
C1—C31.39 (6)C10—H121.09 (4)
C1—C41.39 (8)C10—H131.09 (10)
C3—C51.39 (2)C11—C121.54 (10)
C3—H21.08 (8)C11—H151.02 (11)
C4—C61.39 (3)C12—H161.09 (4)
C4—H31.08 (6)C12—H171.09 (9)
C5—C81.40 (8)C12—H181.09 (6)
O1—S1—O2122 (3)C4—C6—H6119 (4)
O1—S1—N1106 (4)C8—C6—H6120 (2)
O1—S1—C1108 (5)N2—C7—H7111 (4)
O2—S1—N1105 (4)N2—C7—H8110 (5)
O2—S1—C1108 (4)H7—C7—H8125 (3)
N1—S1—C1106.0 (13)C5—C8—C6118 (2)
S1—N1—C2130.4 (11)C5—C8—C10121 (4)
C2—N2—C7121 (6)C6—C8—C10121 (5)
S1—C1—C3119 (4)C8—C10—H11111 (3)
S1—C1—C4120 (3)C8—C10—H12111.4 (11)
C3—C1—C4121 (2)C8—C10—H13111 (7)
O3—C2—N1118 (5)H11—C10—H12107 (8)
O3—C2—N2126 (2)H11—C10—H13107 (4)
N1—C2—N2116 (6)H12—C10—H13108 (5)
C1—C3—C5119 (5)C9—C11—C12111 (7)
C1—C3—H2120 (2)C9—C11—H15114 (4)
C5—C3—H2121 (4)C12—C11—H15113 (4)
C1—C4—C6119 (4)C11—C12—H16111 (8)
C1—C4—H3120 (3)C11—C12—H17114 (3)
C6—C4—H3121 (6)C11—C12—H18108 (5)
C3—C5—C8121 (4)H16—C12—H17108 (4)
C3—C5—H5119 (6)H16—C12—H18108 (2)
C8—C5—H5120 (3)H17—C12—H18108 (9)
C4—C6—C8121 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···C11i1.01 (6)2.48 (2)3.43 (3)156 (7)
N2—H4···O3ii1.01 (10)2.10 (7)3.01 (8)150 (3)
C7—H8···O1ii1.01 (7)2.30 (10)3.19 (11)146 (3)
C10—H11···O1iii1.09 (9)2.47 (5)3.017 (9)109 (6)
C12—H18···N1iii1.09 (6)2.33 (5)3.215 (14)137 (9)
Symmetry codes: (i) x, y+1, z; (ii) x1, y+3, z+1/2; (iii) x, y1, z.
(Tolbutamide_II) N-[(butylamino)carbonyl]-4-methylbenzenesulfonamide top
Crystal data top
C12H18N2O3SZ = 8
Mr = 270.35F(000) = 1152.0
Monoclinic, PcDx = 1.265 Mg m3
a = 9.1685 (6) ÅCu Kα radiation, λ = 1.54180 Å
b = 17.181 (2) ÅT = 298 K
c = 18.152 (2) Åcolourless
β = 96.6067 (4)°?, ? × ? × ? mm
V = 2840.3 (9) Å3
Data collection top
Bruker D8
diffractometer
Scan method: step
Radiation source: sealed X-ray tube2θmin = 5°, 2θmax = 50°, 2θstep = 0.017°
None monochromator
Refinement top
Refinement on Inet59 parameters
Least-squares matrix: full with fixed elements per cycle0 restraints
Rp = 0.1020 constraints
Rwp = 0.137H-atom parameters not refined
Rexp = 0.042Weighting scheme based on measured s.u.'s 1/[Yi + σ(Yi)]
RBragg = 0.047(Δ/σ)max = 0.01
χ2 = 10.562Background function: Chebychev of order 9
2695 data pointsPreferred orientation correction: spherical harmonics order 4
Profile function: fundamental parameter
Crystal data top
C12H18N2O3Sβ = 96.6067 (4)°
Mr = 270.35V = 2840.3 (9) Å3
Monoclinic, PcZ = 8
a = 9.1685 (6) ÅCu Kα radiation, λ = 1.54180 Å
b = 17.181 (2) ÅT = 298 K
c = 18.152 (2) Å?, ? × ? × ? mm
Data collection top
Bruker D8
diffractometer
2θmin = 5°, 2θmax = 50°, 2θstep = 0.017°
Scan method: step
Refinement top
Rp = 0.1022695 data points
Rwp = 0.13759 parameters
Rexp = 0.0420 restraints
RBragg = 0.047H-atom parameters not refined
χ2 = 10.562
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S1a0.1180 (19)0.0570 (8)0.4451 (4)0.043 (6)
O1a0.0405 (19)0.0691 (9)0.43349 (2)0.043 (6)
O2a0.210 (2)0.0946 (7)0.5043 (7)0.043 (6)
N1a0.1704 (10)0.0818 (10)0.3635 (6)0.043 (6)
C1a0.151 (2)0.0436 (8)0.4502 (2)0.043 (6)
C2a0.038 (2)0.0945 (9)0.4269 (6)0.043 (6)
H1a0.072 (3)0.0711 (9)0.4093 (10)0.043 (6)
C3a0.2913 (19)0.0704 (7)0.4734 (3)0.043 (6)
C4a0.066 (3)0.1736 (8)0.4270 (5)0.043 (6)
O3a0.05998 (12)0.0723 (4)0.29787 (16)0.043 (6)
N2a0.1439 (11)0.0577 (10)0.2381 (6)0.043 (6)
C5a0.317 (2)0.1498 (7)0.4731 (4)0.043 (6)
H2a0.3781 (16)0.0282 (7)0.4899 (6)0.043 (6)
C6a0.206 (2)0.2025 (8)0.450179 (11)0.043 (6)
H3a0.023 (3)0.2146 (9)0.4088 (8)0.043 (6)
C7a0.235 (3)0.2876 (7)0.45149 (11)0.043 (6)
H4a0.4279 (19)0.1718 (7)0.4910 (8)0.043 (6)
C8a0.073418 (2)0.0704 (8)0.2986 (3)0.043 (6)
H5a0.2326 (17)0.3113 (7)0.50794 (6)0.043 (6)
H6a0.343 (3)0.3009 (7)0.4344 (5)0.043 (6)
C9a0.0974 (15)0.0999 (9)0.1707 (5)0.043 (6)
H7a0.152 (3)0.3193 (8)0.41436 (16)0.043 (6)
H8a0.2270 (15)0.1344 (12)0.3675 (8)0.043 (6)
C10a0.0582 (4)0.1840 (8)0.1844 (3)0.043 (6)
C11a0.183342 (15)0.2404 (12)0.1797 (8)0.043 (6)
H9a0.2508 (12)0.0383 (13)0.2460 (10)0.043 (6)
H10a0.189 (2)0.0967 (12)0.1365 (9)0.043 (6)
H11a0.002 (2)0.0697 (7)0.14093 (18)0.043 (6)
H12a0.0201 (5)0.1885 (7)0.23984 (16)0.043 (6)
H13a0.0359 (7)0.2002 (6)0.14347 (2)0.043 (6)
C12a0.1299 (5)0.3192 (11)0.1513 (6)0.043 (6)
H14a0.2449 (8)0.2472 (14)0.2355 (10)0.043 (6)
H15a0.2622 (8)0.2157 (15)0.1440 (11)0.043 (6)
H16a0.2199 (9)0.3619 (13)0.1525 (9)0.043 (6)
H17a0.0488 (13)0.3426 (8)0.1861 (3)0.043 (6)
H18a0.0759 (3)0.3155 (9)0.0938 (5)0.043 (6)
O1b0.619 (3)1.0676 (8)0.1800 (11)0.043 (6)
S1b0.466 (3)1.0495 (16)0.1754 (3)0.043 (6)
O2b0.383 (4)1.083 (2)0.12005 (10)0.043 (6)
N1b0.3678 (16)1.0791 (18)0.25547 (2)0.043 (6)
C1b0.4427 (8)0.9487 (17)0.178324 (11)0.043 (6)
C2b0.33234 (14)0.918 (2)0.2288 (3)0.043 (6)
H1b0.2565 (6)0.957 (2)0.2615 (2)0.043 (6)
C3b0.5389 (3)0.9011 (14)0.13420 (9)0.043 (6)
C4b0.3198 (12)0.838 (2)0.2356 (5)0.043 (6)
O3b0.55109 (10)1.0440 (11)0.3228 (8)0.043 (6)
N2b0.3367 (4)1.0869 (18)0.383976 (14)0.043 (6)
C5b0.5241 (11)0.8212 (15)0.1418 (4)0.043 (6)
H2b0.6249 (9)0.9270 (12)0.09495 (8)0.043 (6)
C6b0.4155 (18)0.7885 (17)0.1925 (6)0.043 (6)
H3b0.2332 (18)0.813 (2)0.2751 (7)0.043 (6)
H4b0.5997 (15)0.7829 (12)0.1076 (4)0.043 (6)
C7b0.400 (3)0.7027 (18)0.1998 (9)0.043 (6)
H5b0.322 (3)0.680 (2)0.1628 (10)0.043 (6)
C8b0.4252 (3)1.0692 (15)0.3222 (3)0.043 (6)
H6b0.505 (4)0.6728 (13)0.1845 (8)0.043 (6)
H7b0.358 (4)0.6856 (17)0.2568 (9)0.043 (6)
C9b0.3985 (12)1.1148 (15)0.4493 (3)0.043 (6)
H8b0.2575 (17)1.074 (2)0.2525 (5)0.043 (6)
H9b0.2332 (7)1.064 (2)0.3908 (5)0.043 (6)
C10b0.3402 (7)1.1940 (16)0.47448 (16)0.043 (6)
C11b0.4419 (4)1.2609 (13)0.4509 (6)0.043 (6)
H10b0.5186 (11)1.1166 (11)0.4347 (8)0.043 (6)
H11b0.375 (3)1.0722 (15)0.4948 (3)0.043 (6)
H12b0.23334 (9)1.204 (2)0.4532 (3)0.043 (6)
H13b0.3165 (17)1.1925 (16)0.53555 (12)0.043 (6)
C12b0.3822 (9)1.3380 (15)0.4807 (4)0.043 (6)
H14b0.4590 (14)1.2639 (14)0.3894 (6)0.043 (6)
H15b0.55128 (13)1.2502 (9)0.4693 (11)0.043 (6)
H16b0.4544 (17)1.3870 (13)0.4614 (8)0.043 (6)
H17b0.2733 (14)1.3492 (19)0.46231 (4)0.043 (6)
H18b0.36879 (12)1.3386 (15)0.5419 (4)0.043 (6)
S1c0.1043 (11)0.4548 (16)0.2928 (5)0.043 (6)
O1c0.2600 (15)0.475 (2)0.2850 (6)0.043 (6)
O2c0.0002 (16)0.4903 (10)0.3482 (4)0.043 (6)
N1c0.0577 (17)0.4722 (13)0.2085 (4)0.043 (6)
C1c0.0892 (8)0.3533 (15)0.3014 (6)0.043 (6)
C2c0.200 (3)0.307 (2)0.2669 (3)0.043 (6)
H1c0.299 (3)0.334 (3)0.2382 (10)0.043 (6)
C3c0.0373 (6)0.3212 (8)0.3387 (15)0.043 (6)
C4c0.184 (4)0.227 (2)0.27023 (15)0.043 (6)
O3c0.2690 (18)0.4181 (15)0.1483 (6)0.043 (6)
N2c0.071 (2)0.4390 (11)0.0851 (3)0.043 (6)
C5c0.051 (2)0.2410 (7)0.3413 (16)0.043 (6)
H2c0.1234 (9)0.3601 (3)0.364 (2)0.043 (6)
C6c0.059 (4)0.1926 (13)0.3075 (8)0.043 (6)
H3c0.271 (6)0.189 (3)0.2433 (8)0.043 (6)
C7c0.043 (6)0.1066 (12)0.3120 (9)0.043 (6)
H4c0.151 (2)0.21490 (13)0.370 (2)0.043 (6)
C8c0.1432 (19)0.4408 (13)0.1463 (5)0.043 (6)
H5c0.073 (5)0.0847 (15)0.3655 (5)0.043 (6)
H6c0.070 (7)0.0882 (5)0.3075 (18)0.043 (6)
C9c0.146 (3)0.4667 (10)0.0157 (4)0.043 (6)
H7c0.116 (8)0.0774 (16)0.2676 (4)0.043 (6)
H8c0.025 (2)0.5297 (13)0.2038 (4)0.043 (6)
C10c0.196 (3)0.5506 (11)0.0191 (6)0.043 (6)
C11c0.072 (3)0.6090 (10)0.0278 (6)0.043 (6)
H9c0.042 (2)0.4409 (10)0.09222 (14)0.043 (6)
H10c0.067 (3)0.4602 (9)0.0257 (3)0.043 (6)
H11c0.241 (3)0.4287 (11)0.0007 (5)0.043 (6)
H12c0.262 (3)0.5569 (13)0.0660 (8)0.043 (6)
H13c0.270 (4)0.5633 (11)0.0321 (8)0.043 (6)
C12c0.107 (3)0.6785 (11)0.0734 (7)0.043 (6)
H14c0.029 (3)0.5802 (9)0.0551 (4)0.043 (6)
H15c0.045 (4)0.6276 (8)0.0275 (5)0.043 (6)
H16c0.013 (4)0.7187 (10)0.0841 (7)0.043 (6)
H17c0.137 (3)0.6594 (12)0.1279 (8)0.043 (6)
H18c0.201 (4)0.7117 (11)0.0456 (9)0.043 (6)
O1d0.1459 (4)0.4570 (15)0.0114 (7)0.043 (6)
S1d0.3008 (5)0.4403 (15)0.0139 (12)0.043 (6)
O2d0.3933 (12)0.4737 (16)0.0375 (16)0.043 (6)
N1d0.3851 (5)0.4716 (15)0.0968 (15)0.043 (6)
C1d0.3273 (4)0.3397 (15)0.0190 (12)0.043 (6)
C2d0.4015 (6)0.3089 (15)0.0835 (12)0.043 (6)
H1d0.4505 (8)0.3481 (15)0.1270 (12)0.043 (6)
C3d0.2669 (2)0.2923 (15)0.0384 (13)0.043 (6)
C4d0.4135 (6)0.2289 (15)0.0905 (12)0.043 (6)
O3d0.1762 (14)0.4575 (13)0.1516 (8)0.043 (6)
N2d0.389 (2)0.4807 (13)0.2246 (14)0.043 (6)
C5d0.28044 (19)0.2124 (15)0.0303 (13)0.043 (6)
H2d0.4717 (7)0.2037 (15)0.1410 (12)0.043 (6)
C6d0.3528 (4)0.1795 (15)0.0341 (13)0.043 (6)
H3d0.4709 (2)0.0736 (14)0.0225 (12)0.043 (6)
H4d0.2770 (2)0.0631 (15)0.0089 (14)0.043 (6)
C7d0.3676 (3)0.0938 (15)0.0419 (13)0.043 (6)
H5d0.3695 (5)0.0755 (15)0.1002 (13)0.043 (6)
C8d0.3096 (14)0.4698 (13)0.1586 (12)0.043 (6)
H6d0.4954 (5)0.4607 (15)0.1013 (18)0.043 (6)
H7d0.500 (2)0.4719 (13)0.2288 (18)0.043 (6)
C9d0.319 (3)0.4797 (11)0.2922 (11)0.043 (6)
H8d0.218 (3)0.4450 (11)0.2801 (8)0.043 (6)
H9d0.390 (4)0.4490 (11)0.3362 (13)0.043 (6)
C10d0.284 (4)0.5605 (11)0.3185 (11)0.043 (6)
C11d0.374 (3)0.6246 (12)0.2890 (15)0.043 (6)
H10d0.299 (4)0.5615 (10)0.3798 (11)0.043 (6)
H11d0.165 (3)0.5711 (11)0.3023 (8)0.043 (6)
H12d0.485 (4)0.6255 (12)0.3208 (18)0.043 (6)
H13d0.390 (2)0.6121 (13)0.2306 (16)0.043 (6)
C12d0.304 (3)0.7037 (12)0.2944 (14)0.043 (6)
H14d0.372 (3)0.7506 (12)0.2751 (17)0.043 (6)
H15d0.288 (4)0.7166 (11)0.3525 (13)0.043 (6)
H16d0.196 (3)0.7062 (12)0.2611 (10)0.043 (6)
H17d0.20896 (9)0.3184 (15)0.0885 (13)0.043 (6)
H18d0.23262 (3)0.1743 (15)0.0750 (13)0.043 (6)
Geometric parameters (Å, º) top
S1a—O1a1.46 (2)S1c—O1c1.46 (2)
S1a—O2a1.441 (19)S1c—O2c1.442 (19)
S1a—N1a1.664 (15)S1c—N1c1.662 (14)
S1a—C1a1.75 (2)S1c—C1c1.75 (4)
N1a—C8a1.406 (11)N1c—C8c1.406 (18)
N1a—H8a1.04 (2)N1c—H8c1.04 (3)
C1a—C2a1.39 (2)C1c—C2c1.39 (3)
C1a—C3a1.39 (2)C1c—C3c1.387 (18)
C2a—H1a1.09 (3)C2c—H1c1.09 (4)
C2a—C4a1.38 (2)C2c—C4c1.38 (5)
C3a—C5a1.385 (17)C3c—C5c1.384 (18)
C3a—H2a1.09 (2)C3c—H2c1.093 (19)
C4a—C6a1.39 (3)C4c—C6c1.39 (5)
C4a—H3a1.10 (3)C4c—H3c1.10 (6)
O3a—C8a1.2221 (12)O3c—C8c1.22 (3)
N2a—C8a1.356 (13)N2c—C8c1.356 (18)
N2a—C9a1.441 (17)N2c—C9c1.442 (17)
N2a—H9a1.030 (17)N2c—H9c1.03 (3)
C5a—C6a1.39 (2)C5c—C6c1.39 (3)
C5a—H4a1.10 (2)C5c—H4c1.10 (3)
C6a—C7a1.486 (19)C6c—C7c1.49 (3)
C7a—H5a1.104 (8)C7c—H5c1.11 (3)
C7a—H6a1.10 (3)C7c—H6c1.10 (8)
C7a—H7a1.10 (2)C7c—H7c1.10 (5)
C9a—C10a1.52 (2)C9c—C10c1.52 (3)
C9a—H10a1.10 (2)C9c—H10c1.10 (3)
C9a—H11a1.10 (2)C9c—H11c1.10 (3)
C10a—C11a1.511 (16)C10c—C11c1.51 (4)
C10a—H12a1.106 (7)C10c—H12c1.11 (3)
C10a—H13a1.106 (7)C10c—H13c1.11 (3)
C11a—C12a1.51 (3)C11c—C12c1.51 (3)
C11a—H14a1.11 (2)C11c—H14c1.11 (3)
C11a—H15a1.11 (2)C11c—H15c1.11 (2)
C12a—H16a1.10 (2)C12c—H16c1.10 (4)
C12a—H17a1.105 (15)C12c—H17c1.10 (2)
C12a—H18a1.104 (12)C12c—H18c1.10 (4)
O1b—S1b1.45 (3)O1d—S1d1.444 (9)
S1b—O2b1.45 (3)S1d—O2d1.45 (3)
S1b—N1b1.699 (18)S1d—N1d1.70 (3)
S1b—C1b1.75 (4)S1d—C1d1.75 (4)
N1b—C8b1.383 (10)N1d—C8d1.38 (3)
N1b—H8b1.02 (2)N1d—H6d1.022 (9)
C1b—C2b1.389 (18)C1d—C2d1.39 (3)
C1b—C3b1.39 (2)C1d—C3d1.39 (3)
C2b—H1b1.09 (3)C2d—H1d1.09 (3)
C2b—C4b1.38 (5)C2d—C4d1.38 (4)
C3b—C5b1.38 (3)C3d—C5d1.38 (4)
C3b—H2b1.095 (14)C3d—H17d1.09 (3)
C4b—C6b1.40 (3)C4d—H2d1.10 (3)
C4b—H3b1.10 (3)C4d—C6d1.40 (3)
O3b—C8b1.234 (12)O3d—C8d1.233 (19)
N2b—C8b1.343 (10)N2d—C8d1.34 (3)
N2b—C9b1.453 (15)N2d—H7d1.02 (3)
N2b—H9b1.019 (19)N2d—C9d1.45 (3)
C5b—C6b1.39 (2)C5d—C6d1.40 (3)
C5b—H4b1.10 (2)C5d—H18d1.09 (3)
C6b—C7b1.49 (4)C6d—C7d1.48 (4)
C7b—H5b1.11 (4)H3d—C7d1.104 (18)
C7b—H6b1.10 (4)H4d—C7d1.10 (2)
C7b—H7b1.10 (3)C7d—H5d1.10 (3)
C9b—C10b1.51 (3)C9d—H8d1.10 (3)
C9b—H10b1.103 (15)C9d—H9d1.11 (3)
C9b—H11b1.11 (2)C9d—C10d1.51 (3)
C10b—C11b1.51 (3)C10d—C11d1.51 (4)
C10b—H12b1.106 (9)C10d—H10d1.11 (3)
C10b—H13b1.104 (4)C10d—H11d1.10 (4)
C11b—C12b1.51 (3)C11d—H12d1.11 (4)
C11b—H14b1.110 (15)C11d—H13d1.11 (4)
C11b—H15b1.109 (11)C11d—C12d1.51 (3)
C12b—H16b1.10 (3)C12d—H14d1.10 (4)
C12b—H17b1.106 (16)C12d—H15d1.10 (4)
C12b—H18b1.102 (10)C12d—H16d1.10 (4)
O1a—S1a—O2a122.2 (13)O1c—S1c—O2c122.1 (19)
O1a—S1a—N1a102.7 (7)O1c—S1c—N1c102.7 (11)
O1a—S1a—C1a108.0 (12)O1c—S1c—C1c108 (2)
O2a—S1a—N1a110.1 (13)O2c—S1c—N1c110.2 (13)
O2a—S1a—C1a108.7 (10)O2c—S1c—C1c108.6 (12)
N1a—S1a—C1a103.5 (9)N1c—S1c—C1c103.6 (13)
S1a—N1a—C8a119.4 (9)S1c—N1c—C8c119.4 (15)
S1a—N1a—H8a110.8 (13)S1c—N1c—H8c110.8 (15)
C8a—N1a—H8a116.1 (15)C8c—N1c—H8c116.1 (14)
S1a—C1a—C2a119.2 (14)S1c—C1c—C2c119.1 (16)
S1a—C1a—C3a119.4 (13)S1c—C1c—C3c119.5 (13)
C2a—C1a—C3a121.4 (14)C2c—C1c—C3c121 (2)
C1a—C2a—H1a119.2 (17)C1c—C2c—H1c119 (4)
C1a—C2a—C4a119.1 (18)C1c—C2c—C4c119 (2)
H1a—C2a—C4a121.8 (19)H1c—C2c—C4c122 (4)
C1a—C3a—C5a118.7 (14)C1c—C3c—C5c118.7 (16)
C1a—C3a—H2a119.0 (13)C1c—C3c—H2c118.9 (16)
C5a—C3a—H2a122.3 (17)C5c—C3c—H2c122.4 (14)
C2a—C4a—C6a121.0 (17)C2c—C4c—C6c121 (3)
C2a—C4a—H3a120 (2)C2c—C4c—H3c120 (4)
C6a—C4a—H3a119.0 (17)C6c—C4c—H3c119 (4)
C8a—N2a—C9a119.0 (12)C8c—N2c—C9c118.9 (19)
C8a—N2a—H9a118.2 (14)C8c—N2c—H9c118.3 (10)
C9a—N2a—H9a117.8 (15)C9c—N2c—H9c117.8 (15)
C3a—C5a—C6a121.3 (16)C3c—C5c—C6c121.3 (19)
C3a—C5a—H4a119.5 (15)C3c—C5c—H4c119.5 (16)
C6a—C5a—H4a119.2 (14)C6c—C5c—H4c119.2 (16)
C4a—C6a—C5a118.5 (13)C4c—C6c—C5c119 (2)
C4a—C6a—C7a120.8 (16)C4c—C6c—C7c121 (3)
C5a—C6a—C7a120.7 (17)C5c—C6c—C7c121 (3)
C6a—C7a—H5a110.8 (10)C6c—C7c—H5c111 (3)
C6a—C7a—H6a111.4 (16)C6c—C7c—H6c111 (4)
C6a—C7a—H7a111.5 (17)C6c—C7c—H7c112 (3)
H5a—C7a—H6a107.3 (17)H5c—C7c—H6c107 (4)
H5a—C7a—H7a107.5 (17)H5c—C7c—H7c108 (4)
H6a—C7a—H7a108.1 (16)H6c—C7c—H7c108 (4)
N1a—C8a—O3a122.7 (6)N1c—C8c—O3c122.7 (12)
N1a—C8a—N2a112.8 (6)N1c—C8c—N2c112.8 (16)
O3a—C8a—N2a124.5 (6)O3c—C8c—N2c124.4 (13)
N2a—C9a—C10a113.1 (9)N2c—C9c—C10c113.2 (11)
N2a—C9a—H10a106.4 (14)N2c—C9c—H10c106 (2)
N2a—C9a—H11a108.7 (13)N2c—C9c—H11c108.6 (16)
C10a—C9a—H10a110.4 (16)C10c—C9c—H10c110.4 (17)
C10a—C9a—H11a109.7 (13)C10c—C9c—H11c110 (2)
H10a—C9a—H11a108.3 (15)H10c—C9c—H11c108.2 (16)
C9a—C10a—C11a114.0 (9)C9c—C10c—C11c114 (2)
C9a—C10a—H12a108.7 (11)C9c—C10c—H12c108.7 (18)
C9a—C10a—H13a108.2 (10)C9c—C10c—H13c108.2 (16)
C11a—C10a—H12a109.1 (10)C11c—C10c—H12c109.1 (18)
C11a—C10a—H13a109.8 (11)C11c—C10c—H13c109.7 (19)
H12a—C10a—H13a106.8 (6)H12c—C10c—H13c107 (3)
C10a—C11a—C12a112.1 (6)C10c—C11c—C12c112 (2)
C10a—C11a—H14a109.0 (15)C10c—C11c—H14c109.0 (18)
C10a—C11a—H15a109.7 (19)C10c—C11c—H15c109.8 (18)
C12a—C11a—H14a109.1 (19)C12c—C11c—H14c109.1 (15)
C12a—C11a—H15a110.7 (18)C12c—C11c—H15c110.7 (16)
H14a—C11a—H15a106.0 (11)H14c—C11c—H15c106 (3)
C11a—C12a—H16a112.2 (11)C11c—C12c—H16c112 (3)
C11a—C12a—H17a110.2 (13)C11c—C12c—H17c110.3 (18)
C11a—C12a—H18a111.3 (16)C11c—C12c—H18c111.3 (17)
H16a—C12a—H17a107.3 (18)H16c—C12c—H17c107.4 (19)
H16a—C12a—H18a108.1 (15)H16c—C12c—H18c108 (2)
H17a—C12a—H18a107.6 (8)H17c—C12c—H18c108 (3)
O1b—S1b—O2b123 (2)O1d—S1d—O2d123.2 (18)
O1b—S1b—N1b108.0 (13)O1d—S1d—N1d108.1 (15)
O1b—S1b—C1b109.2 (16)O1d—S1d—C1d109.2 (15)
O2b—S1b—N1b101.8 (18)O2d—S1d—N1d101.8 (14)
O2b—S1b—C1b109.8 (19)O2d—S1d—C1d109.7 (16)
N1b—S1b—C1b102.7 (14)N1d—S1d—C1d102.7 (15)
S1b—N1b—C8b119.5 (15)S1d—N1d—C8d119.5 (10)
S1b—N1b—H8b110.9 (15)S1d—N1d—H6d111 (3)
C8b—N1b—H8b120.8 (11)C8d—N1d—H6d121 (3)
S1b—C1b—C2b118.4 (19)S1d—C1d—C2d118.2 (19)
S1b—C1b—C3b119.9 (13)S1d—C1d—C3d120.0 (17)
C2b—C1b—C3b122 (3)C2d—C1d—C3d122 (2)
C1b—C2b—H1b120 (3)C1d—C2d—H1d120 (3)
C1b—C2b—C4b118.9 (19)C1d—C2d—C4d119 (2)
H1b—C2b—C4b122 (2)H1d—C2d—C4d122 (2)
C1b—C3b—C5b118.6 (12)C1d—C3d—C5d119 (2)
C1b—C3b—H2b120 (2)C1d—C3d—H17d120 (3)
C5b—C3b—H2b121.5 (17)C5d—C3d—H17d122 (2)
C2b—C4b—C6b121.0 (15)C2d—C4d—H2d120 (2)
C2b—C4b—H3b120 (3)C2d—C4d—C6d121.1 (19)
C6b—C4b—H3b119 (4)H2d—C4d—C6d119 (3)
C8b—N2b—C9b120.2 (6)C8d—N2d—H7d119 (3)
C8b—N2b—H9b119 (2)C8d—N2d—C9d120.1 (18)
C9b—N2b—H9b118.1 (8)H7d—N2d—C9d118 (3)
C3b—C5b—C6b121.3 (16)C3d—C5d—C6d121 (2)
C3b—C5b—H4b119.4 (14)C3d—C5d—H18d119 (2)
C6b—C5b—H4b119 (3)C6d—C5d—H18d119 (3)
C4b—C6b—C5b119 (3)C4d—C6d—C5d119 (2)
C4b—C6b—C7b120.5 (19)C4d—C6d—C7d120.6 (19)
C5b—C6b—C7b121 (2)C5d—C6d—C7d121 (2)
C6b—C7b—H5b111 (3)C6d—C7d—H3d111 (2)
C6b—C7b—H6b112 (3)C6d—C7d—H4d111.6 (19)
C6b—C7b—H7b112 (2)C6d—C7d—H5d111 (2)
H5b—C7b—H6b107 (3)H3d—C7d—H4d107 (3)
H5b—C7b—H7b107 (3)H3d—C7d—H5d107.3 (19)
H6b—C7b—H7b108 (3)H4d—C7d—H5d108 (2)
N1b—C8b—O3b120.2 (11)N1d—C8d—O3d120.2 (18)
N1b—C8b—N2b116.7 (10)N1d—C8d—N2d116.6 (15)
O3b—C8b—N2b123.1 (9)O3d—C8d—N2d123 (2)
N2b—C9b—C10b112.7 (15)N2d—C9d—H8d106.6 (19)
N2b—C9b—H10b106.6 (10)N2d—C9d—H9d109 (3)
N2b—C9b—H11b109 (2)N2d—C9d—C10d112.7 (18)
C10b—C9b—H10b111 (2)H8d—C9d—H9d107 (2)
C10b—C9b—H11b109.8 (14)H8d—C9d—C10d111 (3)
H10b—C9b—H11b107 (2)H9d—C9d—C10d110 (2)
C9b—C10b—C11b114.4 (9)C9d—C10d—C11d114 (2)
C9b—C10b—H12b109 (2)C9d—C10d—H10d108.9 (19)
C9b—C10b—H13b108 (2)C9d—C10d—H11d108 (2)
C11b—C10b—H12b109 (2)C11d—C10d—H10d109 (2)
C11b—C10b—H13b110 (2)C11d—C10d—H11d110 (2)
H12b—C10b—H13b105.9 (10)H10d—C10d—H11d106 (3)
C10b—C11b—C12b112.3 (9)C10d—C11d—H12d109 (2)
C10b—C11b—H14b109.4 (16)C10d—C11d—H13d110 (2)
C10b—C11b—H15b109.7 (17)C10d—C11d—C12d112 (2)
C12b—C11b—H14b108.8 (19)H12d—C11d—H13d106 (3)
C12b—C11b—H15b110.0 (15)H12d—C11d—C12d109 (2)
H14b—C11b—H15b106.4 (13)H13d—C11d—C12d110 (2)
C11b—C12b—H16b112.1 (12)C11d—C12d—H14d112 (3)
C11b—C12b—H17b110 (2)C11d—C12d—H15d110 (2)
C11b—C12b—H18b111 (2)C11d—C12d—H16d111 (2)
H16b—C12b—H17b108 (2)H14d—C12d—H15d108 (3)
H16b—C12b—H18b108 (2)H14d—C12d—H16d108 (3)
H17b—C12b—H18b107.6 (8)H15d—C12d—H16d108 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2a—H1a···O1a1.09 (3)2.46 (2)2.91 (2)102.9 (15)
C5a—H4a···C4di1.10 (2)2.40 (2)3.15 (2)124.4 (11)
C5a—H4a···C6di1.10 (2)2.12 (2)3.085 (19)146.0 (14)
C5a—H4a···C7di1.10 (2)2.43 (2)3.09 (2)116.8 (12)
C7a—H6a···C2di1.10 (3)2.40 (3)3.49 (2)167.6 (12)
C7a—H7a···O3cii1.10 (2)2.37 (3)2.92 (2)109 (2)
C7a—H7a···N2cii1.10 (2)2.18 (3)3.04 (2)132.3 (11)
C7a—H7a···C8cii1.10 (2)2.36 (2)3.23 (2)135 (2)
N2a—H9a···O1biii1.030 (17)1.86 (3)2.53 (3)119.6 (17)
N2a—H9a···O3biii1.030 (17)2.161 (15)3.042 (12)142.4 (17)
C9a—H10a···O1biii1.10 (2)1.91 (3)2.65 (3)120.4 (14)
C10a—H12a···O3a1.106 (7)2.412 (12)3.102 (11)119.0 (10)
C10a—H12a···C8a1.106 (7)2.318 (16)2.840 (14)106.6 (10)
C2b—H1b···N1b1.09 (3)2.33 (4)2.84 (5)106.4 (18)
C3b—H2b···O2aiv1.095 (14)2.134 (18)3.100 (17)145.5 (19)
N1b—H8b···O3av1.02 (2)1.901 (14)2.841 (14)151.1 (10)
N2b—H9b···O1av1.019 (19)1.848 (17)2.777 (17)150 (3)
N2b—H9b···O3av1.019 (19)2.449 (9)3.139 (5)124.3 (14)
C9b—H10b···O3b1.103 (15)2.37 (2)2.823 (19)102.4 (12)
C2c—H1c···O3c1.09 (4)2.22 (4)2.90 (3)118 (2)
C7c—H7c···N2avi1.10 (5)2.34 (3)3.07 (3)123 (2)
N2c—H9c···O1d1.03 (3)1.861 (18)2.54 (2)120.4 (6)
N2c—H9c···O3d1.03 (3)1.57 (2)2.47 (2)142.4 (11)
C9c—H10c···O1d1.10 (3)1.99 (3)2.69 (3)117.5 (13)
C2d—H1d···N1d1.09 (3)2.26 (4)2.81 (4)109.2 (19)
C7d—H3d···C3avii1.104 (18)2.174 (18)3.196 (18)153 (2)
C7d—H3d···C5avii1.104 (18)2.34 (2)3.09 (2)124 (2)
N1d—H6d···O3cviii1.022 (9)2.35 (2)3.330 (19)161 (3)
N2d—H7d···O1cviii1.02 (3)2.32 (2)3.28 (2)156 (3)
C9d—H8d···O3d1.10 (3)2.33 (2)2.76 (2)100.7 (16)
C10d—H10d···S1dix1.11 (3)2.43 (3)3.53 (3)173 (3)
C10d—H10d···O2dix1.11 (3)1.75 (3)2.75 (3)148 (3)
C10d—H11d···O2c1.10 (4)2.28 (3)2.97 (3)118.3 (16)
C11d—H13d···N2d1.11 (4)2.26 (3)2.75 (3)104 (2)
C12d—H15d···C3dix1.10 (4)2.02 (3)3.09 (4)164 (2)
C12d—H15d···C5dix1.10 (4)2.46 (3)3.52 (3)161 (2)
C3d—H17d···C12dx1.09 (3)2.42 (4)3.09 (4)118.5 (15)
C5d—H18d···O2bxi1.09 (3)2.30 (4)2.97 (4)117.9 (11)
Symmetry codes: (i) x1, y, z1/2; (ii) x, y, z1/2; (iii) x1, y1, z; (iv) x+1, y+1, z+1/2; (v) x, y+1, z; (vi) x, y, z+1/2; (vii) x+1, y, z+1/2; (viii) x+1, y, z; (ix) x, y+1, z+1/2; (x) x, y+1, z1/2; (xi) x, y1, z.
(Tolbutamide_III) N-[(butylamino)carbonyl]-4-methylbenzenesulfonamide top
Crystal data top
C12H18N2O3SZ = 4
Mr = 270.35F(000) = 576
Monoclinic, P21/nDx = 1.239 Mg m3
a = 11.8094 (5) ÅCu Kα radiation, λ = 1.54180 Å
b = 9.0615 (4) ÅT = 298 K
c = 13.9908 (9) Åcolourless
β = 104.584 (2)°?, ? × ? × ? mm
V = 1448.9 (2) Å3
Data collection top
Bruker D8
diffractometer
Scan method: step
Radiation source: sealed X-ray tube2θmin = 5°, 2θmax = 50°, 2θstep = 0.017°
None monochromator
Refinement top
Refinement on Inet35 parameters
Least-squares matrix: full with fixed elements per cycle0 restraints
Rp = 0.0700 constraints
Rwp = 0.099H-atom parameters not refined
Rexp = 0.042Weighting scheme based on measured s.u.'s 1/[Yi + σ(Yi)]
RBragg = 0.053(Δ/σ)max = 0.01
χ2 = 5.712Background function: Chebychev of order 6
2695 data pointsPreferred orientation correction: spherical harmonics order 4
Profile function: fundamental parameter
Crystal data top
C12H18N2O3Sβ = 104.584 (2)°
Mr = 270.35V = 1448.9 (2) Å3
Monoclinic, P21/nZ = 4
a = 11.8094 (5) ÅCu Kα radiation, λ = 1.54180 Å
b = 9.0615 (4) ÅT = 298 K
c = 13.9908 (9) Å?, ? × ? × ? mm
Data collection top
Bruker D8
diffractometer
2θmin = 5°, 2θmax = 50°, 2θstep = 0.017°
Scan method: step
Refinement top
Rp = 0.0702695 data points
Rwp = 0.09935 parameters
Rexp = 0.0420 restraints
RBragg = 0.053H-atom parameters not refined
χ2 = 5.712
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S11.3596 (5)0.8014 (9)0.3775 (2)0.096 (2)
O11.3372 (10)0.9064 (9)0.4594 (2)0.096 (2)
O21.33743 (18)0.6443 (10)0.39224 (16)0.096 (2)
N11.2759 (3)0.8557 (13)0.30232 (7)0.096 (2)
C11.5084 (4)0.8249 (5)0.3081 (6)0.096 (2)
C21.2566 (2)0.7879 (15)0.2155 (2)0.096 (2)
H11.2084 (5)0.9219 (15)0.3357 (2)0.096 (2)
C31.5840 (5)0.9087 (10)0.3482 (11)0.096 (2)
C41.54686 (15)0.7584 (5)0.2159 (3)0.096 (2)
O31.2776 (5)0.6571 (14)0.20260 (16)0.096 (2)
N21.2131 (3)0.8770 (17)0.1558 (4)0.096 (2)
C51.6998 (5)0.9248 (6)0.2950 (14)0.096 (2)
H21.5519 (7)0.9626 (17)0.4189 (13)0.096 (2)
C61.66298 (9)0.7758 (9)0.1638 (5)0.096 (2)
H31.48641 (3)0.6964 (9)0.18480 (15)0.096 (2)
C71.19464 (14)0.822 (2)0.06267 (11)0.096 (2)
H41.1817 (6)0.9769 (14)0.1818 (6)0.096 (2)
C81.7413 (2)0.8583 (3)0.2025 (11)0.096 (2)
H51.7586 (6)0.9910 (11)0.3256 (18)0.096 (2)
H61.69302 (9)0.7250 (16)0.0916 (3)0.096 (2)
C91.3013 (2)0.7418 (10)0.0012 (7)0.096 (2)
H71.1716 (12)0.917 (3)0.02264 (11)0.096 (2)
H81.1195 (5)0.748 (3)0.0801 (3)0.096 (2)
C101.86771 (17)0.8736 (7)0.1464 (13)0.096 (2)
C111.404392 (1)0.845729 (4)0.0423 (3)0.096 (2)
H91.3284 (3)0.6545 (17)0.0427 (14)0.096 (2)
H101.2751 (6)0.6872 (2)0.0621 (14)0.096 (2)
H111.9205 (2)0.7850 (4)0.1663 (10)0.096 (2)
H121.877757 (17)0.8674 (15)0.0667 (13)0.096 (2)
H131.9046 (3)0.9782 (4)0.1629 (19)0.096 (2)
C121.51654 (2)0.7642 (3)0.0942 (6)0.096 (2)
H141.42097 (19)0.9132 (19)0.0179 (11)0.096 (2)
H151.38032 (19)0.9231 (15)0.0942 (11)0.096 (2)
H161.58823 (9)0.8412 (6)0.1232 (2)0.096 (2)
H171.54478 (12)0.6890 (13)0.0435 (15)0.096 (2)
H181.50340 (12)0.699 (2)0.1562 (14)0.096 (2)
Geometric parameters (Å, º) top
S1—O11.461 (8)C6—H61.085 (10)
S1—O21.453 (12)C7—C91.533 (11)
S1—N11.688 (7)C7—H71.09 (2)
S1—C11.794 (7)C7—H81.09 (2)
N1—C21.430 (8)C8—C101.508 (7)
C1—C31.393 (12)C9—C111.532 (6)
C1—C41.392 (7)C9—H91.097 (19)
C2—O31.215 (18)C9—H101.095 (19)
C2—N21.353 (13)C10—H111.095 (11)
C3—C51.390 (10)C10—H121.09 (3)
C3—H21.08 (2)C10—H131.092 (12)
C4—C61.390 (3)C11—C121.530 (3)
C4—H31.083 (6)C11—H141.098 (16)
N2—C71.461 (10)C11—H151.097 (15)
C5—C81.40 (2)C12—H161.093 (4)
C5—H51.08 (2)C12—H171.095 (18)
C6—C81.400 (11)C12—H181.09 (2)
O1—S1—O2122.4 (4)C9—C7—H8109.8 (18)
O1—S1—N1106.3 (7)H7—C7—H8107.7 (13)
O1—S1—C1107.8 (6)C5—C8—C6118.4 (5)
O2—S1—N1105.1 (5)C5—C8—C10120.8 (9)
O2—S1—C1108.1 (4)C6—C8—C10120.8 (11)
N1—S1—C1106.0 (3)C7—C9—C11112.7 (9)
S1—N1—C2130.4 (8)C7—C9—H9109.2 (10)
S1—C1—C3119.1 (6)C7—C9—H10108.5 (5)
S1—C1—C4119.8 (4)C11—C9—H9109.7 (5)
C3—C1—C4121.1 (6)C11—C9—H10109.8 (8)
N1—C2—O3118.4 (7)H9—C9—H10106.8 (13)
N1—C2—N2115.8 (11)C8—C10—H11110.7 (10)
O3—C2—N2125.8 (7)C8—C10—H12111.5 (10)
C1—C3—C5119.0 (12)C8—C10—H13111.4 (10)
C1—C3—H2120.1 (8)H11—C10—H12107.4 (12)
C5—C3—H2120.8 (12)H11—C10—H13107.4 (12)
C1—C4—C6119.0 (5)H12—C10—H13108.3 (18)
C1—C4—H3120.2 (3)C9—C11—C12113.1 (3)
C6—C4—H3120.8 (5)C9—C11—H14109.5 (7)
C2—N2—C7120.9 (13)C9—C11—H15109.1 (5)
C3—C5—C8121.2 (10)C12—C11—H14109.4 (4)
C3—C5—H5119.2 (17)C12—C11—H15109.4 (6)
C8—C5—H5119.6 (11)H14—C11—H15106.1 (11)
C4—C6—C8121.2 (7)C11—C12—H16111.4 (3)
C4—C6—H6119.2 (6)C11—C12—H17111.2 (8)
C8—C6—H6119.6 (5)C11—C12—H18111.1 (4)
N2—C7—C9113.3 (5)H16—C12—H17107.6 (5)
N2—C7—H7107.7 (17)H16—C12—H18107.6 (9)
N2—C7—H8107.9 (5)H17—C12—H18107.6 (13)
C9—C7—H7110.3 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i1.013 (12)2.194 (18)2.808 (17)117.4 (8)
C4—H3···O31.083 (6)2.441 (6)3.360 (7)141.9 (4)
N2—H4···O2i1.011 (18)1.882 (14)2.622 (17)127.4 (8)
N2—H4···O3i1.011 (18)2.430 (14)3.239 (16)136.5 (7)
C6—H6···O1ii1.085 (10)2.480 (10)3.489 (9)154.1 (4)
C7—H7···O2i1.09 (2)2.37 (2)2.99 (2)114.1 (9)
C9—H9···O31.097 (19)2.165 (19)2.898 (11)121.8 (11)
Symmetry codes: (i) x5/2, y+1/2, z+1/2; (ii) x1/2, y+3/2, z1/2.
(Glycine) Aminoethanoic acid top
Crystal data top
C2H5NO2Z = 4
Mr = 75.07F(000) = 160
Monoclinic, P21/cDx = 1.608 Mg m3
a = 5.10422 (8) ÅCu Kα radiation, λ = 1.54180 Å
b = 11.97177 (17) ÅT = 298 K
c = 5.93652 (9) Åcolourless
β = 121.2642 (8)°?, ? × ? × ? mm
V = 310.08 (1) Å3
Data collection top
Bruker D8
diffractometer
Scan method: step
Radiation source: sealed X-ray tube2θmin = 7.5°, 2θmax = 130°, 2θstep = 0.017°
None monochromator
Refinement top
Refinement on Inet25 parameters
Least-squares matrix: full with fixed elements per cycle0 restraints
Rp = 0.0790 constraints
Rwp = 0.113H-atom parameters not refined
Rexp = 0.012Weighting scheme based on measured s.u.'s 1/[Yi + σ(Yi)]
RBragg = 0.033(Δ/σ)max = 0.01
χ2 = 93.316Background function: Chebychev of order 3
7333 data pointsPreferred orientation correction: March-Dollase (0 1 0)(1 0 2)
Profile function: fundamental parameter
Crystal data top
C2H5NO2β = 121.2642 (8)°
Mr = 75.07V = 310.08 (1) Å3
Monoclinic, P21/cZ = 4
a = 5.10422 (8) ÅCu Kα radiation, λ = 1.54180 Å
b = 11.97177 (17) ÅT = 298 K
c = 5.93652 (9) Å?, ? × ? × ? mm
Data collection top
Bruker D8
diffractometer
2θmin = 7.5°, 2θmax = 130°, 2θstep = 0.017°
Scan method: step
Refinement top
Rp = 0.0797333 data points
Rwp = 0.11325 parameters
Rexp = 0.0120 restraints
RBragg = 0.033H-atom parameters not refined
χ2 = 93.316
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2773 (8)0.8486 (2)0.2168 (5)0.0312 (5)
C20.0136 (4)0.87285 (7)0.0576 (3)0.0312 (5)
H10.641 (4)0.8829 (18)0.146 (4)0.0312 (5)
H20.533 (2)0.9932 (3)0.244 (6)0.0312 (5)
H30.751 (2)0.896 (2)0.4571 (18)0.0312 (5)
H40.2160 (10)0.8788 (5)0.3611 (6)0.0312 (5)
H50.3194 (12)0.7570 (2)0.2410 (9)0.0312 (5)
N10.5766 (9)0.91038 (19)0.2706 (4)0.0312 (5)
O10.0650 (5)0.9062 (2)0.2321 (5)0.0312 (5)
O20.2579 (6)0.8587 (2)0.1128 (4)0.0312 (5)
Geometric parameters (Å, º) top
C1—C21.508 (3)C2—O21.259 (3)
C1—H41.114 (6)H1—N11.01 (3)
C1—H51.112 (3)H2—N11.010 (5)
C1—N11.574 (6)H3—N11.011 (9)
C2—O11.259 (4)
C2—C1—H4108.6 (3)O1—C2—O2119.99 (16)
C2—C1—H5109.5 (3)C1—N1—H1110.5 (11)
C2—C1—N1110.9 (2)C1—N1—H2108.6 (9)
H4—C1—H5109.5 (5)C1—N1—H3110.7 (10)
H4—C1—N1108.8 (3)H1—N1—H2109 (2)
H5—C1—N1109.6 (4)H1—N1—H3108.4 (13)
C1—C2—O1120.0 (2)H2—N1—H3109.3 (19)
C1—C2—O2120.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i1.01 (3)1.88 (3)2.876 (5)169.4 (18)
N1—H2···O1ii1.010 (5)2.410 (19)2.942 (5)112.0 (14)
N1—H2···O2iii1.010 (5)2.142 (7)3.096 (4)156.7 (9)
N1—H3···C2iv1.011 (9)2.483 (10)3.442 (2)158.1 (10)
N1—H3···O1iv1.011 (9)1.709 (8)2.701 (3)166 (2)
C1—H5···O1v1.112 (3)2.397 (5)3.303 (4)137.5 (5)
C1—H5···O2vi1.112 (3)2.320 (5)3.212 (4)135.8 (4)
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+2, z; (iii) x, y+2, z; (iv) x+1, y, z+1; (v) x, y+3/2, z+1/2; (vi) x+1, y+3/2, z+1/2.
(paracetamol) N-(4-hydroxyphenyl)ethanamide top
Crystal data top
C8H9NO2Z = 4
Mr = 151.17F(000) = 320
Monoclinic, P21/nDx = 1.297 Mg m3
a = 11.7144 (5) ÅCu Kα radiation, λ = 1.54180 Å
b = 9.3854 (2) ÅT = 298 K
c = 7.10166 (4) Åcolourless
β = 82.58786 (2)°?, ? × ? × ? mm
V = 774.27 (1) Å3
Data collection top
Bruker D8
diffractometer
Scan method: step
Radiation source: sealed X-ray tube2θmin = 7.5°, 2θmax = 130°, 2θstep = 0.017°
None monochromator
Refinement top
Refinement on Inet25 parameters
Least-squares matrix: full with fixed elements per cycle0 restraints
Rp = 0.1415 constraints
Rwp = 0.188H-atom parameters not refined
Rexp = 0.011Weighting scheme based on measured s.u.'s 1/[Yi + σ(Yi)]
RBragg = 0.080(Δ/σ)max = 0.01
χ2 = 295.840Background function: Chebychev of order 3
7333 data pointsPreferred orientation correction: Spherical Harmonics Order 2
Profile function: fundamental parameter
Crystal data top
C8H9NO2β = 82.58786 (2)°
Mr = 151.17V = 774.27 (1) Å3
Monoclinic, P21/nZ = 4
a = 11.7144 (5) ÅCu Kα radiation, λ = 1.54180 Å
b = 9.3854 (2) ÅT = 298 K
c = 7.10166 (4) Å?, ? × ? × ? mm
Data collection top
Bruker D8
diffractometer
2θmin = 7.5°, 2θmax = 130°, 2θstep = 0.017°
Scan method: step
Refinement top
Rp = 0.1417333 data points
Rwp = 0.18825 parameters
Rexp = 0.0110 restraints
RBragg = 0.080H-atom parameters not refined
χ2 = 295.840
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.0701 (4)0.14232 (12)0.5691 (5)0.0409 (5)
C20.0009 (5)0.14126 (6)0.7482 (3)0.0409 (5)
C30.0408 (3)0.2331 (3)0.4233 (5)0.0409 (5)
C40.0971 (4)0.23059 (14)0.7813 (3)0.0409 (5)
C50.05720 (16)0.3225 (3)0.4563 (5)0.0409 (5)
C60.1262 (2)0.3213 (3)0.6352 (4)0.0409 (5)
C70.2227 (4)0.0036 (3)0.6776 (5)0.0409 (5)
C80.3325 (4)0.0876 (3)0.6302 (6)0.0409 (5)
N10.1683 (5)0.053863 (14)0.5337 (5)0.0409 (5)
O10.22024 (17)0.4070 (4)0.6670 (3)0.0409 (5)
O20.1824 (3)0.0136 (5)0.8416 (5)0.0409 (5)
H10.0235 (6)0.07025 (6)0.8630 (3)0.0409 (5)
H20.09483 (18)0.2342 (3)0.2827 (6)0.0409 (5)
H30.1512 (5)0.22957 (10)0.92181 (18)0.0409 (5)
H40.07994 (4)0.3936 (5)0.3417 (5)0.0409 (5)
H50.24099 (6)0.4718 (5)0.5626 (3)0.0409 (5)
H60.2026 (6)0.0295 (3)0.3928 (5)0.0409 (5)
H70.4076 (4)0.0147 (3)0.6253 (3)0.0409 (5)
H80.3327 (5)0.13970 (4)0.4897 (8)0.0409 (5)
H90.3381 (3)0.1702 (4)0.7408 (8)0.0409 (5)
Geometric parameters (Å, º) top
C1—C21.417 (5)C5—H41.111 (5)
C1—C31.417 (4)C6—O11.359 (4)
C1—N11.414 (6)C7—C81.509 (6)
C2—C41.416 (6)C7—N11.382 (6)
C2—H11.111 (4)C7—O21.210 (5)
C3—C51.417 (4)C8—H71.111 (6)
C3—H21.111 (5)C8—H81.111 (7)
C4—C61.417 (3)C8—H91.112 (6)
C4—H31.111 (4)N1—H61.054 (5)
C5—C61.415 (4)O1—H51.012 (4)
C2—C1—C3119.7 (3)C4—C6—O1120.0 (2)
C2—C1—N1120.9 (3)C5—C6—O1120.1 (2)
C3—C1—N1119.4 (3)C8—C7—N1120.0 (3)
C1—C2—C4120.2 (2)C8—C7—O2120.0 (4)
C1—C2—H1120.0 (5)N1—C7—O2120.0 (4)
C4—C2—H1119.9 (4)C7—C8—H7109.5 (3)
C1—C3—C5120.2 (3)C7—C8—H8109.5 (5)
C1—C3—H2119.9 (3)C7—C8—H9109.5 (4)
C5—C3—H2119.9 (3)H7—C8—H8109.4 (4)
C2—C4—C6120.0 (2)H7—C8—H9109.4 (5)
C2—C4—H3120.0 (3)H8—C8—H9109.5 (4)
C6—C4—H3120.0 (4)C1—N1—C7122.7 (3)
C3—C5—C6120.0 (3)C1—N1—H6119.9 (5)
C3—C5—H4120.0 (3)C7—N1—H6117.5 (5)
C6—C5—H4120.0 (3)C6—O1—H5120.1 (2)
C4—C6—C5119.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H1···O21.111 (4)1.923 (8)2.600 (6)115.3 (5)
O1—H5···O2i1.012 (4)1.911 (4)2.806 (5)145.8 (4)
N1—H6···O1ii1.054 (5)1.836 (5)2.784 (4)147.5 (3)
Symmetry codes: (i) x1/2, y1/2, z1/2; (ii) x+1/2, y1/2, z1/2.
(Lactose_monohydrate) /b-D-galactopyranosyl-(1,4)-D-glucose monhydrate top
Crystal data top
C12H24O12Z = 2
Mr = 360.31F(000) = 384
Monoclinic, P21Dx = 1.540 Mg m3
a = 7.7721 (4) ÅCu Kα radiation, λ = 1.54180 Å
b = 21.58192 (17) ÅT = 298 K
c = 4.8172 (3) Åcolourless
β = 74.0609 (12)°?, ? × ? × ? mm
V = 776.96 (9) Å3
Data collection top
Bruker D8
diffractometer
Scan method: step
Radiation source: sealed X-ray tube2θmin = 7.5°, 2θmax = 130°, 2θstep = 0.017°
None monochromator
Refinement top
Refinement on Inet29 parameters
Least-squares matrix: full with fixed elements per cycle0 restraints
Rp = 0.1833 constraints
Rwp = 0.274H-atom parameters not refined
Rexp = 0.011Weighting scheme based on measured s.u.'s 1/[Yi + σ(Yi)]
RBragg = 0.105(Δ/σ)max = 0.01
χ2 = 576.000Background function: Chebychev of order 3
7333 data pointsPreferred orientation correction: Spherical Harmonics Order 4
Profile function: fundamental parameter
Crystal data top
C12H24O12β = 74.0609 (12)°
Mr = 360.31V = 776.96 (9) Å3
Monoclinic, P21Z = 2
a = 7.7721 (4) ÅCu Kα radiation, λ = 1.54180 Å
b = 21.58192 (17) ÅT = 298 K
c = 4.8172 (3) Å?, ? × ? × ? mm
Data collection top
Bruker D8
diffractometer
2θmin = 7.5°, 2θmax = 130°, 2θstep = 0.017°
Scan method: step
Refinement top
Rp = 0.1837333 data points
Rwp = 0.27429 parameters
Rexp = 0.0110 restraints
RBragg = 0.105H-atom parameters not refined
χ2 = 576.000
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.342 (3)0.5844 (2)0.872 (7)0.0477 (19)
C20.543 (4)0.57524 (9)0.824 (3)0.0477 (19)
C30.786 (3)0.5102 (3)0.5782 (9)0.0477 (19)
C40.7846 (15)0.4006 (3)0.4832 (5)0.0477 (19)
C50.5897 (11)0.3833 (6)0.501 (2)0.0477 (19)
C60.5542 (3)0.3147 (7)0.578 (3)0.0477 (19)
C70.6953 (6)0.2734 (4)0.377 (3)0.0477 (19)
C80.9113 (5)0.35487 (5)0.2796 (5)0.0477 (19)
C91.1074 (9)0.3676 (2)0.2704 (10)0.0477 (19)
C100.911 (2)0.5660 (5)0.472 (4)0.0477 (19)
C110.850 (3)0.6217 (5)0.673 (4)0.0477 (19)
C120.650 (2)0.63473 (19)0.71904 (12)0.0477 (19)
O10.2967 (8)0.5790 (2)0.607 (9)0.0477 (19)
O20.603 (3)0.528071 (7)0.609 (3)0.0477 (19)
O30.825 (2)0.4619 (2)0.3673 (3)0.0477 (19)
O40.466 (2)0.4193 (8)0.719 (2)0.0477 (19)
O50.37701 (13)0.2996 (9)0.560 (4)0.0477 (19)
O60.6718 (13)0.2751 (3)0.094 (3)0.0477 (19)
O70.87094 (15)0.29176 (13)0.3714 (14)0.0477 (19)
O81.22360 (5)0.3315 (5)0.0466 (11)0.0477 (19)
O91.095 (3)0.5527 (8)0.460 (8)0.0477 (19)
O100.9545 (15)0.6746 (6)0.547 (7)0.0477 (19)
O110.6272 (4)0.65513 (10)0.4462 (15)0.0477 (19)
H10.1673 (7)0.5836 (5)0.651 (12)0.0477 (19)
H20.302 (3)0.6305 (3)0.963 (8)0.0477 (19)
H30.265 (5)0.5506 (4)1.026 (8)0.0477 (19)
H40.567 (6)0.5601 (3)1.0284 (18)0.0477 (19)
H50.798 (5)0.4936 (5)0.7866 (18)0.0477 (19)
H60.804 (2)0.3973 (3)0.6997 (2)0.0477 (19)
H70.5597 (7)0.3945 (6)0.297 (2)0.0477 (19)
H80.3494 (16)0.3995 (10)0.743 (3)0.0477 (19)
H90.5558 (8)0.3075 (7)0.802 (3)0.0477 (19)
H100.3897 (8)0.2920 (8)0.355 (5)0.0477 (19)
H110.6751 (11)0.2254 (4)0.451 (3)0.0477 (19)
H120.7589 (19)0.24540 (18)0.015 (3)0.0477 (19)
H130.90001 (3)0.359720 (4)0.0583 (7)0.0477 (19)
H141.1333 (12)0.3545 (2)0.4748 (12)0.0477 (19)
H151.1427 (14)0.4163 (3)0.2243 (18)0.0477 (19)
H161.3444 (2)0.3384 (7)0.061 (2)0.0477 (19)
H170.91146 (9)0.5780 (3)0.251 (3)0.0477 (19)
H181.154 (2)0.5932 (9)0.442 (10)0.0477 (19)
H190.878 (5)0.6132 (8)0.881 (6)0.0477 (19)
H200.88556 (2)0.6952 (4)0.431 (5)0.0477 (19)
H210.608 (3)0.6731 (3)0.871166 (1)0.0477 (19)
H220.6036 (9)0.6182 (2)0.345 (3)0.0477 (19)
O1w0.760 (2)0.1719 (2)0.487 (4)0.0477 (19)
H1w0.724 (2)0.1719 (2)0.695 (4)0.0477 (19)
H2w0.649 (2)0.1719 (2)0.436 (4)0.0477 (19)
Geometric parameters (Å, º) top
C1—C21.53 (4)C8—O71.440 (3)
C1—O11.42 (6)C8—H131.098 (4)
C1—H21.10 (2)C9—O81.432 (8)
C1—H31.10 (3)C9—H141.095 (9)
C2—C121.536 (16)C9—H151.094 (8)
C2—O21.434 (14)C10—C111.534 (19)
C2—H41.10 (3)C10—O91.44 (3)
C3—C101.547 (18)C10—H171.10 (3)
C3—O21.44 (3)C11—C121.53 (3)
C3—O31.431 (6)C11—O101.44 (2)
C3—H51.095 (19)C11—H191.10 (4)
C4—C51.539 (15)C12—O111.442 (10)
C4—C81.541 (7)C12—H211.096 (7)
C4—O31.435 (8)O1—H10.974 (9)
C4—H61.096 (8)O4—H80.98 (2)
C5—C61.53 (2)O5—H100.98 (3)
C5—O41.440 (16)O6—H120.974 (13)
C5—H71.097 (15)O8—H160.972 (5)
C6—C71.533 (14)O9—H180.98 (3)
C6—O51.439 (10)O10—H200.98 (3)
C6—H91.10 (2)O11—H220.978 (10)
C7—O61.42 (2)H1—H18i1.06 (7)
C7—O71.415 (7)O1w—H1w0.96 (3)
C7—H111.094 (13)O1w—H2w0.96 (3)
C8—C91.537 (8)
C2—C1—O1110.4 (19)C4—C8—O7111.3 (3)
C2—C1—H2110 (2)C4—C8—H13110.5 (3)
C2—C1—H3111 (3)C9—C8—O7108.0 (3)
O1—C1—H2109 (3)C9—C8—H13107.3 (3)
O1—C1—H3109 (3)O7—C8—H13108.6 (3)
H2—C1—H3107 (3)C8—C9—O8109.9 (4)
C1—C2—C12112.2 (11)C8—C9—H14110.7 (6)
C1—C2—O2108.4 (19)C8—C9—H15111.6 (7)
C1—C2—H4108 (3)O8—C9—H14107.6 (6)
C12—C2—O2108.5 (12)O8—C9—H15107.4 (7)
C12—C2—H4110 (2)H14—C9—H15109.4 (8)
O2—C2—H4109.6 (13)C3—C10—C11110.0 (12)
C10—C3—O2110.0 (9)C3—C10—O9112.8 (13)
C10—C3—O3109.9 (11)C3—C10—H17109.6 (14)
C10—C3—H5111 (2)C11—C10—O9108.6 (18)
O2—C3—O3106.6 (15)C11—C10—H17110.1 (11)
O2—C3—H5109 (2)O9—C10—H17105.7 (18)
O3—C3—H5110.9 (10)C10—C11—C12111.4 (15)
C5—C4—C8109.1 (6)C10—C11—O10108.2 (15)
C5—C4—O3110.7 (10)C10—C11—H19109.6 (17)
C5—C4—H6108.8 (10)C12—C11—O10110.5 (12)
C8—C4—O3107.9 (5)C12—C11—H19110 (2)
C8—C4—H6109.5 (9)O10—C11—H19107 (2)
O3—C4—H6110.9 (7)C2—C12—C11109.1 (12)
C4—C5—C6110.9 (7)C2—C12—O11111.5 (12)
C4—C5—O4111.1 (10)C2—C12—H21112.1 (11)
C4—C5—H7110.2 (7)C11—C12—O11107.2 (10)
C6—C5—O4107.8 (9)C11—C12—H21110.0 (18)
C6—C5—H7111.1 (12)O11—C12—H21106.8 (9)
O4—C5—H7105.6 (11)C1—O1—H1107 (5)
C5—C6—C7111.1 (7)C2—O2—C3112.3 (17)
C5—C6—O5108.5 (11)C3—O3—C4114.5 (3)
C5—C6—H9109.0 (14)C5—O4—H8105.2 (17)
C7—C6—O5111.2 (12)C6—O5—H10105.2 (10)
C7—C6—H9109.8 (11)C7—O6—H12104.2 (14)
O5—C6—H9107.1 (11)C7—O7—C8113.5 (5)
C6—C7—O6109.4 (8)C9—O8—H16106.6 (10)
C6—C7—O7111.5 (8)C10—O9—H18105 (2)
C6—C7—H11109.2 (10)C11—O10—H20105.4 (16)
O6—C7—O7110.7 (8)C12—O11—H22107.1 (8)
O6—C7—H11107.2 (12)O1—H1—H18i100 (5)
O7—C7—H11108.8 (9)O9—H18—H1ii85 (4)
C4—C8—C9111.1 (5)H1w—O1w—H2w105 (2)
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···C10i0.974 (9)2.40 (4)3.25 (3)144 (5)
O1—H1···O9i0.974 (9)1.38 (6)1.98 (4)113 (4)
O9i—H1···C11.38 (6)1.94 (5)3.20 (5)148.0 (11)
O9i—H1···O11.38 (6)0.974 (9)1.98 (4)113 (4)
O9i—H1···O1wiii1.38 (6)2.047 (18)2.85 (2)111 (3)
C1—H3···O9iv1.10 (3)2.14 (5)3.03 (4)136.1 (19)
O4—H8···O50.98 (2)2.32 (3)2.83 (3)112.1 (15)
O4—H8···O8iv0.98 (2)2.114 (19)2.828 (16)128.5 (16)
C6—H9···O6v1.10 (2)1.99 (2)3.00 (2)151.2 (8)
O5—H10···O60.98 (3)2.238 (13)2.784 (17)114.0 (9)
O5—H10···O8i0.98 (3)2.38 (2)3.11 (2)130.5 (12)
C7—H11···O1w1.094 (13)1.362 (14)2.341 (12)144.5 (9)
O1w—H11···C61.362 (14)2.157 (16)3.443 (16)155.4 (14)
O1w—H11···C71.362 (14)1.094 (13)2.341 (12)144.5 (9)
O1w—H11···O61.362 (14)2.03 (2)3.119 (19)132.3 (12)
O1w—H11···O71.362 (14)2.048 (9)2.737 (7)105.0 (8)
C9—H14···O5ii1.095 (9)2.364 (15)3.179 (17)129.8 (7)
O8—H16···O4vi0.972 (5)2.411 (19)2.828 (16)105.3 (10)
O9—H18···O1ii0.98 (3)1.57 (5)1.98 (4)99 (3)
O9—H18···O100.98 (3)2.30 (2)2.83 (2)113.0 (18)
O9—H18···O1wvii0.98 (3)1.89 (2)2.85 (2)165 (4)
O10—H20···O110.98 (3)2.169 (7)2.749 (19)116.4 (11)
O11—H22···O20.978 (10)2.325 (12)2.843 (5)112.2 (11)
O1w—H2w···C1viii0.96 (3)2.39 (3)2.82 (3)106.6 (11)
O1w—H2w···O11viii0.96 (3)2.094 (15)2.956 (16)148.6 (18)
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z; (iii) x+1, y+1/2, z+1; (iv) x1, y, z+1; (v) x, y, z+1; (vi) x+1, y, z1; (vii) x+2, y+1/2, z+1; (viii) x+1, y1/2, z+1.

Experimental details

(Al2O3_BTEM)(CaF2_BTEM)(ZnO_BTEM)(Tolbutamide_IL)
Crystal data
Chemical formulaAl2O3CaF2ZnOC12H18N2O3S
Mr101.9678.0881.39270.35
Crystal system, space groupHexagonal, R3cCubic, Fm3mHexagonal, P63mcOrthorhombic, Pna21
Temperature (K)298298298298
a, b, c (Å)4.75815 (4), 4.75815 (4), 12.98970 (18)5.46321 (5), 5.46321 (5), 5.46321 (5)3.249308 (18), 3.249308 (18), 5.20571 (4)20.3188 (7), 7.84999 (12), 9.1054 (4)
α, β, γ (°)90, 90, 12090, 90, 9090, 90, 12090, 90, 90
V3)254.69 (1)163.06 (1)47.60 (1)1452.33 (14)
Z6424
Radiation typeCu Kα, λ = 1.541802 ÅCu Kα, λ = 1.541802 ÅCu Kα, λ = 1.541802 ÅCu Kα, λ = 1.54180 Å
Specimen shape, size (mm)?, ? × ? × ??, ? × ? × ??, ? × ? × ??, ? × ? × ?
Data collection
DiffractometerPhilips 3020
diffractometer
Philips 3020
diffractometer
Philips 3020
diffractometer
Bruker D8
diffractometer
Specimen mounting????
Data collection mode????
Scan methodStepStepStepStep
2θ values (°)2θmin = 5 2θmax = 150 2θstep = 0.022θmin = 5 2θmax = 150 2θstep = 0.022θmin = 5 2θmax = 150 2θstep = 0.022θmin = 5 2θmax = 50 2θstep = 0.017
Refinement
R factors and goodness of fitRp = 0.118, Rwp = 0.236, Rexp = 0.247, RBragg = 0.018, χ2 = 0.009Rp = 0.127, Rwp = 0.256, Rexp = 0.387, RBragg = 0.015, χ2 = 0.436Rp = 0.079, Rwp = 0.149, Rexp = 0.337, RBragg = 0.018, χ2 = 0.194Rp = 0.083, Rwp = 0.122, Rexp = 0.042, RBragg = 0.054, χ2 = 8.294
No. of data points7250725072502695
No. of parameters12121222
H-atom treatmentH-atom parameters not refined


(Tolbutamide_II)(Tolbutamide_III)(Glycine)(paracetamol)
Crystal data
Chemical formulaC12H18N2O3SC12H18N2O3SC2H5NO2C8H9NO2
Mr270.35270.3575.07151.17
Crystal system, space groupMonoclinic, PcMonoclinic, P21/nMonoclinic, P21/cMonoclinic, P21/n
Temperature (K)298298298298
a, b, c (Å)9.1685 (6), 17.181 (2), 18.152 (2)11.8094 (5), 9.0615 (4), 13.9908 (9)5.10422 (8), 11.97177 (17), 5.93652 (9)11.7144 (5), 9.3854 (2), 7.10166 (4)
α, β, γ (°)90, 96.6067 (4), 9090, 104.584 (2), 9090, 121.2642 (8), 9090, 82.58786 (2), 90
V3)2840.3 (9)1448.9 (2)310.08 (1)774.27 (1)
Z8444
Radiation typeCu Kα, λ = 1.54180 ÅCu Kα, λ = 1.54180 ÅCu Kα, λ = 1.54180 ÅCu Kα, λ = 1.54180 Å
Specimen shape, size (mm)?, ? × ? × ??, ? × ? × ??, ? × ? × ??, ? × ? × ?
Data collection
DiffractometerBruker D8
diffractometer
Bruker D8
diffractometer
Bruker D8
diffractometer
Bruker D8
diffractometer
Specimen mounting????
Data collection mode????
Scan methodStepStepStepStep
2θ values (°)2θmin = 5 2θmax = 50 2θstep = 0.0172θmin = 5 2θmax = 50 2θstep = 0.0172θmin = 7.5 2θmax = 130 2θstep = 0.0172θmin = 7.5 2θmax = 130 2θstep = 0.017
Refinement
R factors and goodness of fitRp = 0.102, Rwp = 0.137, Rexp = 0.042, RBragg = 0.047, χ2 = 10.562Rp = 0.070, Rwp = 0.099, Rexp = 0.042, RBragg = 0.053, χ2 = 5.712Rp = 0.079, Rwp = 0.113, Rexp = 0.012, RBragg = 0.033, χ2 = 93.316Rp = 0.141, Rwp = 0.188, Rexp = 0.011, RBragg = 0.080, χ2 = 295.840
No. of data points2695269573337333
No. of parameters59352525
H-atom treatmentH-atom parameters not refinedH-atom parameters not refinedH-atom parameters not refinedH-atom parameters not refined


(Lactose_monohydrate)
Crystal data
Chemical formulaC12H24O12
Mr360.31
Crystal system, space groupMonoclinic, P21
Temperature (K)298
a, b, c (Å)7.7721 (4), 21.58192 (17), 4.8172 (3)
α, β, γ (°)90, 74.0609 (12), 90
V3)776.96 (9)
Z2
Radiation typeCu Kα, λ = 1.54180 Å
Specimen shape, size (mm)?, ? × ? × ?
Data collection
DiffractometerBruker D8
diffractometer
Specimen mounting?
Data collection mode?
Scan methodStep
2θ values (°)2θmin = 7.5 2θmax = 130 2θstep = 0.017
Refinement
R factors and goodness of fitRp = 0.183, Rwp = 0.274, Rexp = 0.011, RBragg = 0.105, χ2 = 576.000
No. of data points7333
No. of parameters29
H-atom treatmentH-atom parameters not refined

Computer programs: unknown, Topas v4.2 (Bruker AXS GmbH, 2009), PowderSolve / Materials Studio (Accelrys), Diamond 3.1f, CSD.

 

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