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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
CCDC references: 986780; 986781; 986782; 986783; 986784; 986785; 986786; 986787; 986788
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
Al2O3 | F(000) = 300 |
Mr = 101.96 | Dx = 3.989 Mg m−3 |
Hexagonal, R3c | Cu Kα radiation, λ = 1.541802 Å |
a = 4.75815 (4) Å | T = 298 K |
c = 12.98970 (18) Å | colourless |
V = 254.69 (1) Å3 | ?, ? × ? × ? mm |
Z = 6 | |
Data collection top
Philips 3020 diffractometer | Scan method: step |
Radiation source: sealed X-ray tube | 2θmin = 5°, 2θmax = 150°, 2θstep = 0.02° |
Diffracted beam Graphite monochromator | |
Refinement top
Refinement on Inet | Profile function: fundamental parameter |
Least-squares matrix: full with fixed elements per cycle | 12 parameters |
Rp = 0.118 | 0 restraints |
Rwp = 0.236 | 0 constraints |
Rexp = 0.247 | Weighting scheme based on measured s.u.'s 1/[Yi + σ(Yi)] |
RBragg = 0.018 | (Δ/σ)max = 0.01 |
χ2 = 0.009 | Background function: Chebychev of order 3, plus 1/x |
7250 data points | Preferred orientation correction: none |
Excluded region(s): 0 | |
Crystal data top
Al2O3 | V = 254.69 (1) Å3 |
Mr = 101.96 | Z = 6 |
Hexagonal, R3c | Cu Kα radiation, λ = 1.541802 Å |
a = 4.75815 (4) Å | T = 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 = 0.118 | χ2 = 0.009 |
Rwp = 0.236 | 7250 data points |
Rexp = 0.247 | 12 parameters |
RBragg = 0.018 | 0 restraints |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Al1 | 0 | 0 | 0.35229 (7) | 0.0033 (2) | |
O1 | 0.3062 (3) | 0 | 0.25 | 0.0021 (4) | |
Geometric parameters (Å, º) top
Al1—O1 | 1.9719 (14) | Al1—O1iii | 1.8537 (9) |
Al1—O1i | 1.9719 (14) | Al1—O1iv | 1.8537 (9) |
Al1—O1ii | 1.9719 (12) | Al1—O1v | 1.8537 (15) |
| | | |
O1—Al1—O1i | 79.56 (5) | O1ii—Al1—O1v | 86.35 (5) |
O1—Al1—O1ii | 79.56 (6) | O1iii—Al1—O1iv | 101.23 (6) |
O1—Al1—O1iii | 86.35 (4) | O1iii—Al1—O1v | 101.23 (7) |
O1—Al1—O1iv | 90.78 (3) | O1iv—Al1—O1v | 101.23 (6) |
O1—Al1—O1v | 164.13 (7) | Al1—O1—Al1vi | 84.73 (7) |
O1i—Al1—O1ii | 79.56 (6) | Al1—O1—Al1iii | 93.65 (4) |
O1i—Al1—O1iii | 164.13 (7) | Al1—O1—Al1vii | 132.18 (3) |
O1i—Al1—O1iv | 86.35 (4) | Al1vi—O1—Al1iii | 132.18 (3) |
O1i—Al1—O1v | 90.78 (4) | Al1vi—O1—Al1vii | 93.65 (4) |
O1ii—Al1—O1iii | 90.78 (5) | Al1iii—O1—Al1vii | 120.34 (8) |
O1ii—Al1—O1iv | 164.13 (7) | | |
Symmetry codes: (i) −y, x−y, z; (ii) −x+y, −x, z; (iii) −x+1/3, −y−1/3, −z+2/3; (iv) y+1/3, −x+y+2/3, −z+2/3; (v) x−y−2/3, x−1/3, −z+2/3; (vi) y, x, −z+1/2; (vii) −y+2/3, −x+1/3, z−1/6. |
(CaF2_BTEM) calcium fluoride
top
Crystal data top
CaF2 | F(000) = 152 |
Mr = 78.08 | Dx = 3.181 Mg m−3 |
Cubic, Fm3m | Cu Kα radiation, λ = 1.541802 Å |
a = 5.46321 (5) Å | T = 298 K |
V = 163.06 (1) Å3 | colourless |
Z = 4 | ?, ? × ? × ? mm |
Data collection top
Philips 3020 diffractometer | Scan method: step |
Radiation source: sealed X-ray tube | 2θmin = 5°, 2θmax = 150°, 2θstep = 0.02° |
Graphite Monochromator monochromator | |
Refinement top
Refinement on Inet | Profile function: fundamental parameter |
Least-squares matrix: full with fixed elements per cycle | 12 parameters |
Rp = 0.127 | 0 restraints |
Rwp = 0.256 | 0 constraints |
Rexp = 0.387 | Weighting scheme based on measured s.u.'s 1/[Yi + σ(Yi)] |
RBragg = 0.015 | (Δ/σ)max = 0.01 |
χ2 = 0.436 | Background function: Chebychev of order 3, plus 1/x |
7250 data points | Preferred orientation correction: none |
Crystal data top
CaF2 | Z = 4 |
Mr = 78.08 | Cu Kα radiation, λ = 1.541802 Å |
Cubic, Fm3m | T = 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 = 0.127 | χ2 = 0.436 |
Rwp = 0.256 | 7250 data points |
Rexp = 0.387 | 12 parameters |
RBragg = 0.015 | 0 restraints |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Ca1 | 0 | 0 | 0 | 0.0063 (3) | |
F1 | 0.25 | 0.25 | 0.25 | 0.00783 (5) | |
Geometric parameters (Å, º) top
Ca1—F1 | 2.3656 | Ca1—F1iv | 2.3656 |
Ca1—F1i | 2.3656 | Ca1—F1v | 2.3656 |
Ca1—F1ii | 2.3656 | Ca1—F1vi | 2.3656 |
Ca1—F1iii | 2.3656 | Ca1—F1vii | 2.3656 |
| | | |
F1—Ca1—F1i | 109.47 | F1ii—Ca1—F1vii | 70.53 |
F1—Ca1—F1ii | 109.47 | F1iii—Ca1—F1iv | 180.0 (5) |
F1—Ca1—F1iii | 109.47 | F1iii—Ca1—F1v | 70.53 |
F1—Ca1—F1iv | 70.53 | F1iii—Ca1—F1vi | 70.53 |
F1—Ca1—F1v | 70.53 | F1iii—Ca1—F1vii | 70.53 |
F1—Ca1—F1vi | 70.53 | F1iv—Ca1—F1v | 109.47 |
F1—Ca1—F1vii | 180.0 (5) | F1iv—Ca1—F1vi | 109.47 |
F1i—Ca1—F1ii | 109.47 | F1iv—Ca1—F1vii | 109.47 |
F1i—Ca1—F1iii | 109.47 | F1v—Ca1—F1vi | 109.47 |
F1i—Ca1—F1iv | 70.53 | F1v—Ca1—F1vii | 109.47 |
F1i—Ca1—F1v | 70.53 | F1vi—Ca1—F1vii | 109.47 |
F1i—Ca1—F1vi | 180.0 (5) | Ca1—F1—Ca1viii | 109.47 |
F1i—Ca1—F1vii | 70.53 | Ca1—F1—Ca1ix | 109.47 |
F1ii—Ca1—F1iii | 109.47 | Ca1—F1—Ca1x | 109.47 |
F1ii—Ca1—F1iv | 70.53 | Ca1viii—F1—Ca1ix | 109.47 |
F1ii—Ca1—F1v | 180.0 (5) | Ca1viii—F1—Ca1x | 109.47 |
F1ii—Ca1—F1vi | 70.53 | Ca1ix—F1—Ca1x | 109.47 |
Symmetry codes: (i) x, y−1/2, z−1/2; (ii) x−1/2, y, z−1/2; (iii) x−1/2, y−1/2, z; (iv) y, x, −z; (v) y, x−1/2, −z+1/2; (vi) y−1/2, x, −z+1/2; (vii) y−1/2, x−1/2, −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
ZnO | F(000) = 76 |
Mr = 81.39 | Dx = 5.679 Mg m−3 |
Hexagonal, P63mc | Cu Kα radiation, λ = 1.541802 Å |
a = 3.249308 (18) Å | T = 298 K |
c = 5.20571 (4) Å | colourless |
V = 47.60 (1) Å3 | ?, ? × ? × ? mm |
Z = 2 | |
Data collection top
Philips 3020 diffractometer | Scan method: step |
Radiation source: sealed X-ray tube | 2θmin = 5°, 2θmax = 150°, 2θstep = 0.02° |
Graphite Monochromator monochromator | |
Refinement top
Refinement on Inet | Profile function: fundamental parameter |
Least-squares matrix: full with fixed elements per cycle | 12 parameters |
Rp = 0.079 | 0 restraints |
Rwp = 0.149 | 0 constraints |
Rexp = 0.337 | Weighting scheme based on measured s.u.'s 1/[Yi + σ(Yi)] |
RBragg = 0.018 | (Δ/σ)max = 0.01 |
χ2 = 0.194 | Background function: Chebychev of order 3, plus 1/x |
7250 data points | Preferred orientation correction: none |
Excluded region(s): 0 | |
Crystal data top
ZnO | V = 47.60 (1) Å3 |
Mr = 81.39 | Z = 2 |
Hexagonal, P63mc | Cu Kα radiation, λ = 1.541802 Å |
a = 3.249308 (18) Å | T = 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 = 0.079 | χ2 = 0.194 |
Rwp = 0.149 | 7250 data points |
Rexp = 0.337 | 12 parameters |
RBragg = 0.018 | 0 restraints |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Zn | 0.333333 | 0.666667 | 0.5 | 0.00623 (16) | |
O | 0.666667 | 0.333333 | 0.3790 (6) | 0.0058 (8) | |
Geometric parameters (Å, º) top
Zn—Oi | 1.9789 (10) | Zn—Oii | 1.9789 (10) |
Zn—O | 1.9789 (10) | Zn—Oiii | 1.973 (3) |
| | | |
Oi—Zn—O | 110.37 (6) | Zniv—O—Zn | 110.37 (8) |
Oi—Zn—Oii | 110.37 (6) | Zniv—O—Znv | 110.37 (8) |
Oi—Zn—Oiii | 108.56 (9) | Zniv—O—Znvi | 108.56 (9) |
O—Zn—Oii | 110.37 (6) | Zn—O—Znv | 110.37 (8) |
O—Zn—Oiii | 108.56 (9) | Zn—O—Znvi | 108.56 (9) |
Oii—Zn—Oiii | 108.56 (9) | Znv—O—Znvi | 108.56 (9) |
Symmetry codes: (i) x−1, y, z; (ii) x, y+1, z; (iii) −x+1, −y+1, z+1/2; (iv) x, y−1, z; (v) x+1, y, z; (vi) −x+1, −y+1, z−1/2. |
(Tolbutamide_IL)
N-[(butylamino)carbonyl]-4-methylbenzenesulfonamide
top
Crystal data top
C12H18N2O3S | Z = 4 |
Mr = 270.35 | F(000) = 576 |
Orthorhombic, Pna21 | Dx = 1.237 Mg m−3 |
a = 20.3188 (7) Å | Cu Kα radiation, λ = 1.54180 Å |
b = 7.84999 (12) Å | T = 298 K |
c = 9.1054 (4) Å | colourless |
V = 1452.33 (14) Å3 | ?, ? × ? × ? mm |
Data collection top
Bruker D8 diffractometer | Scan method: step |
Radiation source: sealed X-ray tube | 2θmin = 5°, 2θmax = 50°, 2θstep = 0.017° |
None monochromator | |
Refinement top
Refinement on Inet | 22 parameters |
Least-squares matrix: full with fixed elements per cycle | 0 restraints |
Rp = 0.083 | 0 constraints |
Rwp = 0.122 | H-atom parameters not refined |
Rexp = 0.042 | Weighting scheme based on measured s.u.'s 1/[Yi + σ(Yi)] |
RBragg = 0.054 | (Δ/σ)max = 0.01 |
χ2 = 8.294 | Background function: Chebychev of order 2 + 1/X |
2695 data points | Preferred orientation correction: spherical harmonics order 4 |
Profile function: fundamental parameter | |
Crystal data top
C12H18N2O3S | V = 1452.33 (14) Å3 |
Mr = 270.35 | Z = 4 |
Orthorhombic, Pna21 | Cu Kα radiation, λ = 1.54180 Å |
a = 20.3188 (7) Å | T = 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 = 0.083 | 2695 data points |
Rwp = 0.122 | 22 parameters |
Rexp = 0.042 | 0 restraints |
RBragg = 0.054 | H-atom parameters not refined |
χ2 = 8.294 | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | −0.602193 (16) | 1.6660 (5) | −0.301 (9) | 0.1929 (3) | |
O1 | −0.61777 (15) | 1.7862 (7) | −0.418 (10) | 0.1929 (3) | |
O2 | −0.6121 (2) | 1.7069 (3) | −0.147 (9) | 0.1929 (3) | |
O3 | −0.4899 (2) | 1.4162 (7) | −0.477 (8) | 0.1929 (3) | |
N1 | −0.521163 (1) | 1.6223 (5) | −0.316 (9) | 0.1929 (3) | |
N2 | −0.45944 (12) | 1.3852 (4) | −0.237 (8) | 0.1929 (3) | |
C1 | −0.64441 (3) | 1.4705 (5) | −0.339 (9) | 0.1929 (3) | |
C2 | −0.48833 (4) | 1.4663 (6) | −0.351 (8) | 0.1929 (3) | |
C3 | −0.62642 (8) | 1.3235 (4) | −0.263 (9) | 0.1929 (3) | |
C4 | −0.69403 (18) | 1.4671 (7) | −0.445 (10) | 0.1929 (3) | |
C5 | −0.65854 (4) | 1.1715 (5) | −0.295 (9) | 0.1929 (3) | |
C6 | −0.7255 (2) | 1.3138 (7) | −0.475 (10) | 0.1929 (3) | |
C7 | −0.40986 (4) | 1.2537 (4) | −0.262 (8) | 0.1929 (3) | |
C8 | −0.70819 (11) | 1.1638 (6) | −0.401 (10) | 0.1929 (3) | |
C9 | −0.44859 (19) | 1.0544 (10) | −0.266 (11) | 0.1929 (3) | |
C10 | −0.74164 (16) | 0.9974 (6) | −0.437 (10) | 0.1929 (3) | |
C11 | −0.4059 (9) | 0.92120 (10) | −0.221 (10) | 0.1929 (3) | |
C12 | −0.38262 (9) | 0.8152 (12) | −0.353 (10) | 0.1929 (3) | |
H1 | −0.49198 (8) | 1.7019 (5) | −0.258 (9) | 0.1929 (3) | |
H2 | −0.58887 (19) | 1.3294 (3) | −0.179 (9) | 0.1929 (3) | |
H3 | −0.7084 (3) | 1.5831 (7) | −0.500 (10) | 0.1929 (3) | |
H4 | −0.47583 (16) | 1.41013 (11) | −0.135 (8) | 0.1929 (3) | |
H5 | −0.64504 (12) | 1.0572 (4) | −0.235 (9) | 0.1929 (3) | |
H6 | −0.7645 (3) | 1.3110 (8) | −0.556 (10) | 0.1929 (3) | |
H7 | −0.3923 (12) | 1.261 (2) | −0.362 (7) | 0.1929 (3) | |
H8 | −0.3821 (4) | 1.2389 (11) | −0.171 (6) | 0.1929 (3) | |
H9 | −0.4737 (9) | 1.038 (3) | −0.375 (12) | 0.1929 (3) | |
H10 | −0.4973 (9) | 1.0577 (11) | −0.189 (13) | 0.1929 (3) | |
H11 | −0.7152 (3) | 0.9302 (8) | −0.524 (9) | 0.1929 (3) | |
H12 | −0.7920 (2) | 1.0175 (7) | −0.475 (10) | 0.1929 (3) | |
H13 | −0.74313 (3) | 0.9131 (5) | −0.341 (10) | 0.1929 (3) | |
H14 | −0.3586 (11) | 0.9863 (11) | −0.175 (8) | 0.1929 (3) | |
H15 | −0.4243 (18) | 0.84846 (17) | −0.137 (12) | 0.1929 (3) | |
H16 | −0.3479 (7) | 0.71629 (14) | −0.319 (9) | 0.1929 (3) | |
H17 | −0.3591 (8) | 0.8902 (16) | −0.440 (9) | 0.1929 (3) | |
H18 | −0.42550 (14) | 0.752 (3) | −0.401 (12) | 0.1929 (3) | |
Geometric parameters (Å, º) top
S1—O1 | 1.46 (9) | C5—H5 | 1.08 (6) |
S1—O2 | 1.45 (12) | C6—C8 | 1.40 (6) |
S1—N1 | 1.687 (10) | C6—H6 | 1.09 (9) |
S1—C1 | 1.79 (2) | C7—H7 | 0.98 (9) |
O3—C2 | 1.21 (10) | C7—H8 | 1.01 (7) |
N1—C2 | 1.43 (2) | C8—C10 | 1.51 (3) |
N2—C2 | 1.35 (8) | C9—C11 | 1.42 (4) |
N2—C7 | 1.459 (16) | C10—H11 | 1.09 (9) |
C1—C3 | 1.39 (6) | C10—H12 | 1.09 (4) |
C1—C4 | 1.39 (8) | C10—H13 | 1.09 (10) |
C3—C5 | 1.39 (2) | C11—C12 | 1.54 (10) |
C3—H2 | 1.08 (8) | C11—H15 | 1.02 (11) |
C4—C6 | 1.39 (3) | C12—H16 | 1.09 (4) |
C4—H3 | 1.08 (6) | C12—H17 | 1.09 (9) |
C5—C8 | 1.40 (8) | C12—H18 | 1.09 (6) |
| | | |
O1—S1—O2 | 122 (3) | C4—C6—H6 | 119 (4) |
O1—S1—N1 | 106 (4) | C8—C6—H6 | 120 (2) |
O1—S1—C1 | 108 (5) | N2—C7—H7 | 111 (4) |
O2—S1—N1 | 105 (4) | N2—C7—H8 | 110 (5) |
O2—S1—C1 | 108 (4) | H7—C7—H8 | 125 (3) |
N1—S1—C1 | 106.0 (13) | C5—C8—C6 | 118 (2) |
S1—N1—C2 | 130.4 (11) | C5—C8—C10 | 121 (4) |
C2—N2—C7 | 121 (6) | C6—C8—C10 | 121 (5) |
S1—C1—C3 | 119 (4) | C8—C10—H11 | 111 (3) |
S1—C1—C4 | 120 (3) | C8—C10—H12 | 111.4 (11) |
C3—C1—C4 | 121 (2) | C8—C10—H13 | 111 (7) |
O3—C2—N1 | 118 (5) | H11—C10—H12 | 107 (8) |
O3—C2—N2 | 126 (2) | H11—C10—H13 | 107 (4) |
N1—C2—N2 | 116 (6) | H12—C10—H13 | 108 (5) |
C1—C3—C5 | 119 (5) | C9—C11—C12 | 111 (7) |
C1—C3—H2 | 120 (2) | C9—C11—H15 | 114 (4) |
C5—C3—H2 | 121 (4) | C12—C11—H15 | 113 (4) |
C1—C4—C6 | 119 (4) | C11—C12—H16 | 111 (8) |
C1—C4—H3 | 120 (3) | C11—C12—H17 | 114 (3) |
C6—C4—H3 | 121 (6) | C11—C12—H18 | 108 (5) |
C3—C5—C8 | 121 (4) | H16—C12—H17 | 108 (4) |
C3—C5—H5 | 119 (6) | H16—C12—H18 | 108 (2) |
C8—C5—H5 | 120 (3) | H17—C12—H18 | 108 (9) |
C4—C6—C8 | 121 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···C11i | 1.01 (6) | 2.48 (2) | 3.43 (3) | 156 (7) |
N2—H4···O3ii | 1.01 (10) | 2.10 (7) | 3.01 (8) | 150 (3) |
C7—H8···O1ii | 1.01 (7) | 2.30 (10) | 3.19 (11) | 146 (3) |
C10—H11···O1iii | 1.09 (9) | 2.47 (5) | 3.017 (9) | 109 (6) |
C12—H18···N1iii | 1.09 (6) | 2.33 (5) | 3.215 (14) | 137 (9) |
Symmetry codes: (i) x, y+1, z; (ii) −x−1, −y+3, z+1/2; (iii) x, y−1, z. |
(Tolbutamide_II)
N-[(butylamino)carbonyl]-4-methylbenzenesulfonamide
top
Crystal data top
C12H18N2O3S | Z = 8 |
Mr = 270.35 | F(000) = 1152.0 |
Monoclinic, Pc | Dx = 1.265 Mg m−3 |
a = 9.1685 (6) Å | Cu Kα radiation, λ = 1.54180 Å |
b = 17.181 (2) Å | T = 298 K |
c = 18.152 (2) Å | colourless |
β = 96.6067 (4)° | ?, ? × ? × ? mm |
V = 2840.3 (9) Å3 | |
Data collection top
Bruker D8 diffractometer | Scan method: step |
Radiation source: sealed X-ray tube | 2θmin = 5°, 2θmax = 50°, 2θstep = 0.017° |
None monochromator | |
Refinement top
Refinement on Inet | 59 parameters |
Least-squares matrix: full with fixed elements per cycle | 0 restraints |
Rp = 0.102 | 0 constraints |
Rwp = 0.137 | H-atom parameters not refined |
Rexp = 0.042 | Weighting scheme based on measured s.u.'s 1/[Yi + σ(Yi)] |
RBragg = 0.047 | (Δ/σ)max = 0.01 |
χ2 = 10.562 | Background function: Chebychev of order 9 |
2695 data points | Preferred orientation correction: spherical harmonics order 4 |
Profile function: fundamental parameter | |
Crystal data top
C12H18N2O3S | β = 96.6067 (4)° |
Mr = 270.35 | V = 2840.3 (9) Å3 |
Monoclinic, Pc | Z = 8 |
a = 9.1685 (6) Å | Cu Kα radiation, λ = 1.54180 Å |
b = 17.181 (2) Å | T = 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 = 0.102 | 2695 data points |
Rwp = 0.137 | 59 parameters |
Rexp = 0.042 | 0 restraints |
RBragg = 0.047 | H-atom parameters not refined |
χ2 = 10.562 | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1a | −0.1180 (19) | 0.0570 (8) | −0.4451 (4) | 0.043 (6) | |
O1a | 0.0405 (19) | 0.0691 (9) | −0.43349 (2) | 0.043 (6) | |
O2a | −0.210 (2) | 0.0946 (7) | −0.5043 (7) | 0.043 (6) | |
N1a | −0.1704 (10) | 0.0818 (10) | −0.3635 (6) | 0.043 (6) | |
C1a | −0.151 (2) | −0.0436 (8) | −0.4502 (2) | 0.043 (6) | |
C2a | −0.038 (2) | −0.0945 (9) | −0.4269 (6) | 0.043 (6) | |
H1a | 0.072 (3) | −0.0711 (9) | −0.4093 (10) | 0.043 (6) | |
C3a | −0.2913 (19) | −0.0704 (7) | −0.4734 (3) | 0.043 (6) | |
C4a | −0.066 (3) | −0.1736 (8) | −0.4270 (5) | 0.043 (6) | |
O3a | 0.05998 (12) | 0.0723 (4) | −0.29787 (16) | 0.043 (6) | |
N2a | −0.1439 (11) | 0.0577 (10) | −0.2381 (6) | 0.043 (6) | |
C5a | −0.317 (2) | −0.1498 (7) | −0.4731 (4) | 0.043 (6) | |
H2a | −0.3781 (16) | −0.0282 (7) | −0.4899 (6) | 0.043 (6) | |
C6a | −0.206 (2) | −0.2025 (8) | −0.450179 (11) | 0.043 (6) | |
H3a | 0.023 (3) | −0.2146 (9) | −0.4088 (8) | 0.043 (6) | |
C7a | −0.235 (3) | −0.2876 (7) | −0.45149 (11) | 0.043 (6) | |
H4a | −0.4279 (19) | −0.1718 (7) | −0.4910 (8) | 0.043 (6) | |
C8a | −0.073418 (2) | 0.0704 (8) | −0.2986 (3) | 0.043 (6) | |
H5a | −0.2326 (17) | −0.3113 (7) | −0.50794 (6) | 0.043 (6) | |
H6a | −0.343 (3) | −0.3009 (7) | −0.4344 (5) | 0.043 (6) | |
C9a | −0.0974 (15) | 0.0999 (9) | −0.1707 (5) | 0.043 (6) | |
H7a | −0.152 (3) | −0.3193 (8) | −0.41436 (16) | 0.043 (6) | |
H8a | −0.2270 (15) | 0.1344 (12) | −0.3675 (8) | 0.043 (6) | |
C10a | −0.0582 (4) | 0.1840 (8) | −0.1844 (3) | 0.043 (6) | |
C11a | −0.183342 (15) | 0.2404 (12) | −0.1797 (8) | 0.043 (6) | |
H9a | −0.2508 (12) | 0.0383 (13) | −0.2460 (10) | 0.043 (6) | |
H10a | −0.189 (2) | 0.0967 (12) | −0.1365 (9) | 0.043 (6) | |
H11a | −0.002 (2) | 0.0697 (7) | −0.14093 (18) | 0.043 (6) | |
H12a | −0.0201 (5) | 0.1885 (7) | −0.23984 (16) | 0.043 (6) | |
H13a | 0.0359 (7) | 0.2002 (6) | −0.14347 (2) | 0.043 (6) | |
C12a | −0.1299 (5) | 0.3192 (11) | −0.1513 (6) | 0.043 (6) | |
H14a | −0.2449 (8) | 0.2472 (14) | −0.2355 (10) | 0.043 (6) | |
H15a | −0.2622 (8) | 0.2157 (15) | −0.1440 (11) | 0.043 (6) | |
H16a | −0.2199 (9) | 0.3619 (13) | −0.1525 (9) | 0.043 (6) | |
H17a | −0.0488 (13) | 0.3426 (8) | −0.1861 (3) | 0.043 (6) | |
H18a | −0.0759 (3) | 0.3155 (9) | −0.0938 (5) | 0.043 (6) | |
O1b | 0.619 (3) | 1.0676 (8) | −0.1800 (11) | 0.043 (6) | |
S1b | 0.466 (3) | 1.0495 (16) | −0.1754 (3) | 0.043 (6) | |
O2b | 0.383 (4) | 1.083 (2) | −0.12005 (10) | 0.043 (6) | |
N1b | 0.3678 (16) | 1.0791 (18) | −0.25547 (2) | 0.043 (6) | |
C1b | 0.4427 (8) | 0.9487 (17) | −0.178324 (11) | 0.043 (6) | |
C2b | 0.33234 (14) | 0.918 (2) | −0.2288 (3) | 0.043 (6) | |
H1b | 0.2565 (6) | 0.957 (2) | −0.2615 (2) | 0.043 (6) | |
C3b | 0.5389 (3) | 0.9011 (14) | −0.13420 (9) | 0.043 (6) | |
C4b | 0.3198 (12) | 0.838 (2) | −0.2356 (5) | 0.043 (6) | |
O3b | 0.55109 (10) | 1.0440 (11) | −0.3228 (8) | 0.043 (6) | |
N2b | 0.3367 (4) | 1.0869 (18) | −0.383976 (14) | 0.043 (6) | |
C5b | 0.5241 (11) | 0.8212 (15) | −0.1418 (4) | 0.043 (6) | |
H2b | 0.6249 (9) | 0.9270 (12) | −0.09495 (8) | 0.043 (6) | |
C6b | 0.4155 (18) | 0.7885 (17) | −0.1925 (6) | 0.043 (6) | |
H3b | 0.2332 (18) | 0.813 (2) | −0.2751 (7) | 0.043 (6) | |
H4b | 0.5997 (15) | 0.7829 (12) | −0.1076 (4) | 0.043 (6) | |
C7b | 0.400 (3) | 0.7027 (18) | −0.1998 (9) | 0.043 (6) | |
H5b | 0.322 (3) | 0.680 (2) | −0.1628 (10) | 0.043 (6) | |
C8b | 0.4252 (3) | 1.0692 (15) | −0.3222 (3) | 0.043 (6) | |
H6b | 0.505 (4) | 0.6728 (13) | −0.1845 (8) | 0.043 (6) | |
H7b | 0.358 (4) | 0.6856 (17) | −0.2568 (9) | 0.043 (6) | |
C9b | 0.3985 (12) | 1.1148 (15) | −0.4493 (3) | 0.043 (6) | |
H8b | 0.2575 (17) | 1.074 (2) | −0.2525 (5) | 0.043 (6) | |
H9b | 0.2332 (7) | 1.064 (2) | −0.3908 (5) | 0.043 (6) | |
C10b | 0.3402 (7) | 1.1940 (16) | −0.47448 (16) | 0.043 (6) | |
C11b | 0.4419 (4) | 1.2609 (13) | −0.4509 (6) | 0.043 (6) | |
H10b | 0.5186 (11) | 1.1166 (11) | −0.4347 (8) | 0.043 (6) | |
H11b | 0.375 (3) | 1.0722 (15) | −0.4948 (3) | 0.043 (6) | |
H12b | 0.23334 (9) | 1.204 (2) | −0.4532 (3) | 0.043 (6) | |
H13b | 0.3165 (17) | 1.1925 (16) | −0.53555 (12) | 0.043 (6) | |
C12b | 0.3822 (9) | 1.3380 (15) | −0.4807 (4) | 0.043 (6) | |
H14b | 0.4590 (14) | 1.2639 (14) | −0.3894 (6) | 0.043 (6) | |
H15b | 0.55128 (13) | 1.2502 (9) | −0.4693 (11) | 0.043 (6) | |
H16b | 0.4544 (17) | 1.3870 (13) | −0.4614 (8) | 0.043 (6) | |
H17b | 0.2733 (14) | 1.3492 (19) | −0.46231 (4) | 0.043 (6) | |
H18b | 0.36879 (12) | 1.3386 (15) | −0.5419 (4) | 0.043 (6) | |
S1c | −0.1043 (11) | 0.4548 (16) | 0.2928 (5) | 0.043 (6) | |
O1c | −0.2600 (15) | 0.475 (2) | 0.2850 (6) | 0.043 (6) | |
O2c | 0.0002 (16) | 0.4903 (10) | 0.3482 (4) | 0.043 (6) | |
N1c | −0.0577 (17) | 0.4722 (13) | 0.2085 (4) | 0.043 (6) | |
C1c | −0.0892 (8) | 0.3533 (15) | 0.3014 (6) | 0.043 (6) | |
C2c | −0.200 (3) | 0.307 (2) | 0.2669 (3) | 0.043 (6) | |
H1c | −0.299 (3) | 0.334 (3) | 0.2382 (10) | 0.043 (6) | |
C3c | 0.0373 (6) | 0.3212 (8) | 0.3387 (15) | 0.043 (6) | |
C4c | −0.184 (4) | 0.227 (2) | 0.27023 (15) | 0.043 (6) | |
O3c | −0.2690 (18) | 0.4181 (15) | 0.1483 (6) | 0.043 (6) | |
N2c | −0.071 (2) | 0.4390 (11) | 0.0851 (3) | 0.043 (6) | |
C5c | 0.051 (2) | 0.2410 (7) | 0.3413 (16) | 0.043 (6) | |
H2c | 0.1234 (9) | 0.3601 (3) | 0.364 (2) | 0.043 (6) | |
C6c | −0.059 (4) | 0.1926 (13) | 0.3075 (8) | 0.043 (6) | |
H3c | −0.271 (6) | 0.189 (3) | 0.2433 (8) | 0.043 (6) | |
C7c | −0.043 (6) | 0.1066 (12) | 0.3120 (9) | 0.043 (6) | |
H4c | 0.151 (2) | 0.21490 (13) | 0.370 (2) | 0.043 (6) | |
C8c | −0.1432 (19) | 0.4408 (13) | 0.1463 (5) | 0.043 (6) | |
H5c | −0.073 (5) | 0.0847 (15) | 0.3655 (5) | 0.043 (6) | |
H6c | 0.070 (7) | 0.0882 (5) | 0.3075 (18) | 0.043 (6) | |
C9c | −0.146 (3) | 0.4667 (10) | 0.0157 (4) | 0.043 (6) | |
H7c | −0.116 (8) | 0.0774 (16) | 0.2676 (4) | 0.043 (6) | |
H8c | −0.025 (2) | 0.5297 (13) | 0.2038 (4) | 0.043 (6) | |
C10c | −0.196 (3) | 0.5506 (11) | 0.0191 (6) | 0.043 (6) | |
C11c | −0.072 (3) | 0.6090 (10) | 0.0278 (6) | 0.043 (6) | |
H9c | 0.042 (2) | 0.4409 (10) | 0.09222 (14) | 0.043 (6) | |
H10c | −0.067 (3) | 0.4602 (9) | −0.0257 (3) | 0.043 (6) | |
H11c | −0.241 (3) | 0.4287 (11) | −0.0007 (5) | 0.043 (6) | |
H12c | −0.262 (3) | 0.5569 (13) | 0.0660 (8) | 0.043 (6) | |
H13c | −0.270 (4) | 0.5633 (11) | −0.0321 (8) | 0.043 (6) | |
C12c | −0.107 (3) | 0.6785 (11) | 0.0734 (7) | 0.043 (6) | |
H14c | 0.029 (3) | 0.5802 (9) | 0.0551 (4) | 0.043 (6) | |
H15c | −0.045 (4) | 0.6276 (8) | −0.0275 (5) | 0.043 (6) | |
H16c | −0.013 (4) | 0.7187 (10) | 0.0841 (7) | 0.043 (6) | |
H17c | −0.137 (3) | 0.6594 (12) | 0.1279 (8) | 0.043 (6) | |
H18c | −0.201 (4) | 0.7117 (11) | 0.0456 (9) | 0.043 (6) | |
O1d | 0.1459 (4) | 0.4570 (15) | 0.0114 (7) | 0.043 (6) | |
S1d | 0.3008 (5) | 0.4403 (15) | 0.0139 (12) | 0.043 (6) | |
O2d | 0.3933 (12) | 0.4737 (16) | −0.0375 (16) | 0.043 (6) | |
N1d | 0.3851 (5) | 0.4716 (15) | 0.0968 (15) | 0.043 (6) | |
C1d | 0.3273 (4) | 0.3397 (15) | 0.0190 (12) | 0.043 (6) | |
C2d | 0.4015 (6) | 0.3089 (15) | 0.0835 (12) | 0.043 (6) | |
H1d | 0.4505 (8) | 0.3481 (15) | 0.1270 (12) | 0.043 (6) | |
C3d | 0.2669 (2) | 0.2923 (15) | −0.0384 (13) | 0.043 (6) | |
C4d | 0.4135 (6) | 0.2289 (15) | 0.0905 (12) | 0.043 (6) | |
O3d | 0.1762 (14) | 0.4575 (13) | 0.1516 (8) | 0.043 (6) | |
N2d | 0.389 (2) | 0.4807 (13) | 0.2246 (14) | 0.043 (6) | |
C5d | 0.28044 (19) | 0.2124 (15) | −0.0303 (13) | 0.043 (6) | |
H2d | 0.4717 (7) | 0.2037 (15) | 0.1410 (12) | 0.043 (6) | |
C6d | 0.3528 (4) | 0.1795 (15) | 0.0341 (13) | 0.043 (6) | |
H3d | 0.4709 (2) | 0.0736 (14) | 0.0225 (12) | 0.043 (6) | |
H4d | 0.2770 (2) | 0.0631 (15) | 0.0089 (14) | 0.043 (6) | |
C7d | 0.3676 (3) | 0.0938 (15) | 0.0419 (13) | 0.043 (6) | |
H5d | 0.3695 (5) | 0.0755 (15) | 0.1002 (13) | 0.043 (6) | |
C8d | 0.3096 (14) | 0.4698 (13) | 0.1586 (12) | 0.043 (6) | |
H6d | 0.4954 (5) | 0.4607 (15) | 0.1013 (18) | 0.043 (6) | |
H7d | 0.500 (2) | 0.4719 (13) | 0.2288 (18) | 0.043 (6) | |
C9d | 0.319 (3) | 0.4797 (11) | 0.2922 (11) | 0.043 (6) | |
H8d | 0.218 (3) | 0.4450 (11) | 0.2801 (8) | 0.043 (6) | |
H9d | 0.390 (4) | 0.4490 (11) | 0.3362 (13) | 0.043 (6) | |
C10d | 0.284 (4) | 0.5605 (11) | 0.3185 (11) | 0.043 (6) | |
C11d | 0.374 (3) | 0.6246 (12) | 0.2890 (15) | 0.043 (6) | |
H10d | 0.299 (4) | 0.5615 (10) | 0.3798 (11) | 0.043 (6) | |
H11d | 0.165 (3) | 0.5711 (11) | 0.3023 (8) | 0.043 (6) | |
H12d | 0.485 (4) | 0.6255 (12) | 0.3208 (18) | 0.043 (6) | |
H13d | 0.390 (2) | 0.6121 (13) | 0.2306 (16) | 0.043 (6) | |
C12d | 0.304 (3) | 0.7037 (12) | 0.2944 (14) | 0.043 (6) | |
H14d | 0.372 (3) | 0.7506 (12) | 0.2751 (17) | 0.043 (6) | |
H15d | 0.288 (4) | 0.7166 (11) | 0.3525 (13) | 0.043 (6) | |
H16d | 0.196 (3) | 0.7062 (12) | 0.2611 (10) | 0.043 (6) | |
H17d | 0.20896 (9) | 0.3184 (15) | −0.0885 (13) | 0.043 (6) | |
H18d | 0.23262 (3) | 0.1743 (15) | −0.0750 (13) | 0.043 (6) | |
Geometric parameters (Å, º) top
S1a—O1a | 1.46 (2) | S1c—O1c | 1.46 (2) |
S1a—O2a | 1.441 (19) | S1c—O2c | 1.442 (19) |
S1a—N1a | 1.664 (15) | S1c—N1c | 1.662 (14) |
S1a—C1a | 1.75 (2) | S1c—C1c | 1.75 (4) |
N1a—C8a | 1.406 (11) | N1c—C8c | 1.406 (18) |
N1a—H8a | 1.04 (2) | N1c—H8c | 1.04 (3) |
C1a—C2a | 1.39 (2) | C1c—C2c | 1.39 (3) |
C1a—C3a | 1.39 (2) | C1c—C3c | 1.387 (18) |
C2a—H1a | 1.09 (3) | C2c—H1c | 1.09 (4) |
C2a—C4a | 1.38 (2) | C2c—C4c | 1.38 (5) |
C3a—C5a | 1.385 (17) | C3c—C5c | 1.384 (18) |
C3a—H2a | 1.09 (2) | C3c—H2c | 1.093 (19) |
C4a—C6a | 1.39 (3) | C4c—C6c | 1.39 (5) |
C4a—H3a | 1.10 (3) | C4c—H3c | 1.10 (6) |
O3a—C8a | 1.2221 (12) | O3c—C8c | 1.22 (3) |
N2a—C8a | 1.356 (13) | N2c—C8c | 1.356 (18) |
N2a—C9a | 1.441 (17) | N2c—C9c | 1.442 (17) |
N2a—H9a | 1.030 (17) | N2c—H9c | 1.03 (3) |
C5a—C6a | 1.39 (2) | C5c—C6c | 1.39 (3) |
C5a—H4a | 1.10 (2) | C5c—H4c | 1.10 (3) |
C6a—C7a | 1.486 (19) | C6c—C7c | 1.49 (3) |
C7a—H5a | 1.104 (8) | C7c—H5c | 1.11 (3) |
C7a—H6a | 1.10 (3) | C7c—H6c | 1.10 (8) |
C7a—H7a | 1.10 (2) | C7c—H7c | 1.10 (5) |
C9a—C10a | 1.52 (2) | C9c—C10c | 1.52 (3) |
C9a—H10a | 1.10 (2) | C9c—H10c | 1.10 (3) |
C9a—H11a | 1.10 (2) | C9c—H11c | 1.10 (3) |
C10a—C11a | 1.511 (16) | C10c—C11c | 1.51 (4) |
C10a—H12a | 1.106 (7) | C10c—H12c | 1.11 (3) |
C10a—H13a | 1.106 (7) | C10c—H13c | 1.11 (3) |
C11a—C12a | 1.51 (3) | C11c—C12c | 1.51 (3) |
C11a—H14a | 1.11 (2) | C11c—H14c | 1.11 (3) |
C11a—H15a | 1.11 (2) | C11c—H15c | 1.11 (2) |
C12a—H16a | 1.10 (2) | C12c—H16c | 1.10 (4) |
C12a—H17a | 1.105 (15) | C12c—H17c | 1.10 (2) |
C12a—H18a | 1.104 (12) | C12c—H18c | 1.10 (4) |
O1b—S1b | 1.45 (3) | O1d—S1d | 1.444 (9) |
S1b—O2b | 1.45 (3) | S1d—O2d | 1.45 (3) |
S1b—N1b | 1.699 (18) | S1d—N1d | 1.70 (3) |
S1b—C1b | 1.75 (4) | S1d—C1d | 1.75 (4) |
N1b—C8b | 1.383 (10) | N1d—C8d | 1.38 (3) |
N1b—H8b | 1.02 (2) | N1d—H6d | 1.022 (9) |
C1b—C2b | 1.389 (18) | C1d—C2d | 1.39 (3) |
C1b—C3b | 1.39 (2) | C1d—C3d | 1.39 (3) |
C2b—H1b | 1.09 (3) | C2d—H1d | 1.09 (3) |
C2b—C4b | 1.38 (5) | C2d—C4d | 1.38 (4) |
C3b—C5b | 1.38 (3) | C3d—C5d | 1.38 (4) |
C3b—H2b | 1.095 (14) | C3d—H17d | 1.09 (3) |
C4b—C6b | 1.40 (3) | C4d—H2d | 1.10 (3) |
C4b—H3b | 1.10 (3) | C4d—C6d | 1.40 (3) |
O3b—C8b | 1.234 (12) | O3d—C8d | 1.233 (19) |
N2b—C8b | 1.343 (10) | N2d—C8d | 1.34 (3) |
N2b—C9b | 1.453 (15) | N2d—H7d | 1.02 (3) |
N2b—H9b | 1.019 (19) | N2d—C9d | 1.45 (3) |
C5b—C6b | 1.39 (2) | C5d—C6d | 1.40 (3) |
C5b—H4b | 1.10 (2) | C5d—H18d | 1.09 (3) |
C6b—C7b | 1.49 (4) | C6d—C7d | 1.48 (4) |
C7b—H5b | 1.11 (4) | H3d—C7d | 1.104 (18) |
C7b—H6b | 1.10 (4) | H4d—C7d | 1.10 (2) |
C7b—H7b | 1.10 (3) | C7d—H5d | 1.10 (3) |
C9b—C10b | 1.51 (3) | C9d—H8d | 1.10 (3) |
C9b—H10b | 1.103 (15) | C9d—H9d | 1.11 (3) |
C9b—H11b | 1.11 (2) | C9d—C10d | 1.51 (3) |
C10b—C11b | 1.51 (3) | C10d—C11d | 1.51 (4) |
C10b—H12b | 1.106 (9) | C10d—H10d | 1.11 (3) |
C10b—H13b | 1.104 (4) | C10d—H11d | 1.10 (4) |
C11b—C12b | 1.51 (3) | C11d—H12d | 1.11 (4) |
C11b—H14b | 1.110 (15) | C11d—H13d | 1.11 (4) |
C11b—H15b | 1.109 (11) | C11d—C12d | 1.51 (3) |
C12b—H16b | 1.10 (3) | C12d—H14d | 1.10 (4) |
C12b—H17b | 1.106 (16) | C12d—H15d | 1.10 (4) |
C12b—H18b | 1.102 (10) | C12d—H16d | 1.10 (4) |
| | | |
O1a—S1a—O2a | 122.2 (13) | O1c—S1c—O2c | 122.1 (19) |
O1a—S1a—N1a | 102.7 (7) | O1c—S1c—N1c | 102.7 (11) |
O1a—S1a—C1a | 108.0 (12) | O1c—S1c—C1c | 108 (2) |
O2a—S1a—N1a | 110.1 (13) | O2c—S1c—N1c | 110.2 (13) |
O2a—S1a—C1a | 108.7 (10) | O2c—S1c—C1c | 108.6 (12) |
N1a—S1a—C1a | 103.5 (9) | N1c—S1c—C1c | 103.6 (13) |
S1a—N1a—C8a | 119.4 (9) | S1c—N1c—C8c | 119.4 (15) |
S1a—N1a—H8a | 110.8 (13) | S1c—N1c—H8c | 110.8 (15) |
C8a—N1a—H8a | 116.1 (15) | C8c—N1c—H8c | 116.1 (14) |
S1a—C1a—C2a | 119.2 (14) | S1c—C1c—C2c | 119.1 (16) |
S1a—C1a—C3a | 119.4 (13) | S1c—C1c—C3c | 119.5 (13) |
C2a—C1a—C3a | 121.4 (14) | C2c—C1c—C3c | 121 (2) |
C1a—C2a—H1a | 119.2 (17) | C1c—C2c—H1c | 119 (4) |
C1a—C2a—C4a | 119.1 (18) | C1c—C2c—C4c | 119 (2) |
H1a—C2a—C4a | 121.8 (19) | H1c—C2c—C4c | 122 (4) |
C1a—C3a—C5a | 118.7 (14) | C1c—C3c—C5c | 118.7 (16) |
C1a—C3a—H2a | 119.0 (13) | C1c—C3c—H2c | 118.9 (16) |
C5a—C3a—H2a | 122.3 (17) | C5c—C3c—H2c | 122.4 (14) |
C2a—C4a—C6a | 121.0 (17) | C2c—C4c—C6c | 121 (3) |
C2a—C4a—H3a | 120 (2) | C2c—C4c—H3c | 120 (4) |
C6a—C4a—H3a | 119.0 (17) | C6c—C4c—H3c | 119 (4) |
C8a—N2a—C9a | 119.0 (12) | C8c—N2c—C9c | 118.9 (19) |
C8a—N2a—H9a | 118.2 (14) | C8c—N2c—H9c | 118.3 (10) |
C9a—N2a—H9a | 117.8 (15) | C9c—N2c—H9c | 117.8 (15) |
C3a—C5a—C6a | 121.3 (16) | C3c—C5c—C6c | 121.3 (19) |
C3a—C5a—H4a | 119.5 (15) | C3c—C5c—H4c | 119.5 (16) |
C6a—C5a—H4a | 119.2 (14) | C6c—C5c—H4c | 119.2 (16) |
C4a—C6a—C5a | 118.5 (13) | C4c—C6c—C5c | 119 (2) |
C4a—C6a—C7a | 120.8 (16) | C4c—C6c—C7c | 121 (3) |
C5a—C6a—C7a | 120.7 (17) | C5c—C6c—C7c | 121 (3) |
C6a—C7a—H5a | 110.8 (10) | C6c—C7c—H5c | 111 (3) |
C6a—C7a—H6a | 111.4 (16) | C6c—C7c—H6c | 111 (4) |
C6a—C7a—H7a | 111.5 (17) | C6c—C7c—H7c | 112 (3) |
H5a—C7a—H6a | 107.3 (17) | H5c—C7c—H6c | 107 (4) |
H5a—C7a—H7a | 107.5 (17) | H5c—C7c—H7c | 108 (4) |
H6a—C7a—H7a | 108.1 (16) | H6c—C7c—H7c | 108 (4) |
N1a—C8a—O3a | 122.7 (6) | N1c—C8c—O3c | 122.7 (12) |
N1a—C8a—N2a | 112.8 (6) | N1c—C8c—N2c | 112.8 (16) |
O3a—C8a—N2a | 124.5 (6) | O3c—C8c—N2c | 124.4 (13) |
N2a—C9a—C10a | 113.1 (9) | N2c—C9c—C10c | 113.2 (11) |
N2a—C9a—H10a | 106.4 (14) | N2c—C9c—H10c | 106 (2) |
N2a—C9a—H11a | 108.7 (13) | N2c—C9c—H11c | 108.6 (16) |
C10a—C9a—H10a | 110.4 (16) | C10c—C9c—H10c | 110.4 (17) |
C10a—C9a—H11a | 109.7 (13) | C10c—C9c—H11c | 110 (2) |
H10a—C9a—H11a | 108.3 (15) | H10c—C9c—H11c | 108.2 (16) |
C9a—C10a—C11a | 114.0 (9) | C9c—C10c—C11c | 114 (2) |
C9a—C10a—H12a | 108.7 (11) | C9c—C10c—H12c | 108.7 (18) |
C9a—C10a—H13a | 108.2 (10) | C9c—C10c—H13c | 108.2 (16) |
C11a—C10a—H12a | 109.1 (10) | C11c—C10c—H12c | 109.1 (18) |
C11a—C10a—H13a | 109.8 (11) | C11c—C10c—H13c | 109.7 (19) |
H12a—C10a—H13a | 106.8 (6) | H12c—C10c—H13c | 107 (3) |
C10a—C11a—C12a | 112.1 (6) | C10c—C11c—C12c | 112 (2) |
C10a—C11a—H14a | 109.0 (15) | C10c—C11c—H14c | 109.0 (18) |
C10a—C11a—H15a | 109.7 (19) | C10c—C11c—H15c | 109.8 (18) |
C12a—C11a—H14a | 109.1 (19) | C12c—C11c—H14c | 109.1 (15) |
C12a—C11a—H15a | 110.7 (18) | C12c—C11c—H15c | 110.7 (16) |
H14a—C11a—H15a | 106.0 (11) | H14c—C11c—H15c | 106 (3) |
C11a—C12a—H16a | 112.2 (11) | C11c—C12c—H16c | 112 (3) |
C11a—C12a—H17a | 110.2 (13) | C11c—C12c—H17c | 110.3 (18) |
C11a—C12a—H18a | 111.3 (16) | C11c—C12c—H18c | 111.3 (17) |
H16a—C12a—H17a | 107.3 (18) | H16c—C12c—H17c | 107.4 (19) |
H16a—C12a—H18a | 108.1 (15) | H16c—C12c—H18c | 108 (2) |
H17a—C12a—H18a | 107.6 (8) | H17c—C12c—H18c | 108 (3) |
O1b—S1b—O2b | 123 (2) | O1d—S1d—O2d | 123.2 (18) |
O1b—S1b—N1b | 108.0 (13) | O1d—S1d—N1d | 108.1 (15) |
O1b—S1b—C1b | 109.2 (16) | O1d—S1d—C1d | 109.2 (15) |
O2b—S1b—N1b | 101.8 (18) | O2d—S1d—N1d | 101.8 (14) |
O2b—S1b—C1b | 109.8 (19) | O2d—S1d—C1d | 109.7 (16) |
N1b—S1b—C1b | 102.7 (14) | N1d—S1d—C1d | 102.7 (15) |
S1b—N1b—C8b | 119.5 (15) | S1d—N1d—C8d | 119.5 (10) |
S1b—N1b—H8b | 110.9 (15) | S1d—N1d—H6d | 111 (3) |
C8b—N1b—H8b | 120.8 (11) | C8d—N1d—H6d | 121 (3) |
S1b—C1b—C2b | 118.4 (19) | S1d—C1d—C2d | 118.2 (19) |
S1b—C1b—C3b | 119.9 (13) | S1d—C1d—C3d | 120.0 (17) |
C2b—C1b—C3b | 122 (3) | C2d—C1d—C3d | 122 (2) |
C1b—C2b—H1b | 120 (3) | C1d—C2d—H1d | 120 (3) |
C1b—C2b—C4b | 118.9 (19) | C1d—C2d—C4d | 119 (2) |
H1b—C2b—C4b | 122 (2) | H1d—C2d—C4d | 122 (2) |
C1b—C3b—C5b | 118.6 (12) | C1d—C3d—C5d | 119 (2) |
C1b—C3b—H2b | 120 (2) | C1d—C3d—H17d | 120 (3) |
C5b—C3b—H2b | 121.5 (17) | C5d—C3d—H17d | 122 (2) |
C2b—C4b—C6b | 121.0 (15) | C2d—C4d—H2d | 120 (2) |
C2b—C4b—H3b | 120 (3) | C2d—C4d—C6d | 121.1 (19) |
C6b—C4b—H3b | 119 (4) | H2d—C4d—C6d | 119 (3) |
C8b—N2b—C9b | 120.2 (6) | C8d—N2d—H7d | 119 (3) |
C8b—N2b—H9b | 119 (2) | C8d—N2d—C9d | 120.1 (18) |
C9b—N2b—H9b | 118.1 (8) | H7d—N2d—C9d | 118 (3) |
C3b—C5b—C6b | 121.3 (16) | C3d—C5d—C6d | 121 (2) |
C3b—C5b—H4b | 119.4 (14) | C3d—C5d—H18d | 119 (2) |
C6b—C5b—H4b | 119 (3) | C6d—C5d—H18d | 119 (3) |
C4b—C6b—C5b | 119 (3) | C4d—C6d—C5d | 119 (2) |
C4b—C6b—C7b | 120.5 (19) | C4d—C6d—C7d | 120.6 (19) |
C5b—C6b—C7b | 121 (2) | C5d—C6d—C7d | 121 (2) |
C6b—C7b—H5b | 111 (3) | C6d—C7d—H3d | 111 (2) |
C6b—C7b—H6b | 112 (3) | C6d—C7d—H4d | 111.6 (19) |
C6b—C7b—H7b | 112 (2) | C6d—C7d—H5d | 111 (2) |
H5b—C7b—H6b | 107 (3) | H3d—C7d—H4d | 107 (3) |
H5b—C7b—H7b | 107 (3) | H3d—C7d—H5d | 107.3 (19) |
H6b—C7b—H7b | 108 (3) | H4d—C7d—H5d | 108 (2) |
N1b—C8b—O3b | 120.2 (11) | N1d—C8d—O3d | 120.2 (18) |
N1b—C8b—N2b | 116.7 (10) | N1d—C8d—N2d | 116.6 (15) |
O3b—C8b—N2b | 123.1 (9) | O3d—C8d—N2d | 123 (2) |
N2b—C9b—C10b | 112.7 (15) | N2d—C9d—H8d | 106.6 (19) |
N2b—C9b—H10b | 106.6 (10) | N2d—C9d—H9d | 109 (3) |
N2b—C9b—H11b | 109 (2) | N2d—C9d—C10d | 112.7 (18) |
C10b—C9b—H10b | 111 (2) | H8d—C9d—H9d | 107 (2) |
C10b—C9b—H11b | 109.8 (14) | H8d—C9d—C10d | 111 (3) |
H10b—C9b—H11b | 107 (2) | H9d—C9d—C10d | 110 (2) |
C9b—C10b—C11b | 114.4 (9) | C9d—C10d—C11d | 114 (2) |
C9b—C10b—H12b | 109 (2) | C9d—C10d—H10d | 108.9 (19) |
C9b—C10b—H13b | 108 (2) | C9d—C10d—H11d | 108 (2) |
C11b—C10b—H12b | 109 (2) | C11d—C10d—H10d | 109 (2) |
C11b—C10b—H13b | 110 (2) | C11d—C10d—H11d | 110 (2) |
H12b—C10b—H13b | 105.9 (10) | H10d—C10d—H11d | 106 (3) |
C10b—C11b—C12b | 112.3 (9) | C10d—C11d—H12d | 109 (2) |
C10b—C11b—H14b | 109.4 (16) | C10d—C11d—H13d | 110 (2) |
C10b—C11b—H15b | 109.7 (17) | C10d—C11d—C12d | 112 (2) |
C12b—C11b—H14b | 108.8 (19) | H12d—C11d—H13d | 106 (3) |
C12b—C11b—H15b | 110.0 (15) | H12d—C11d—C12d | 109 (2) |
H14b—C11b—H15b | 106.4 (13) | H13d—C11d—C12d | 110 (2) |
C11b—C12b—H16b | 112.1 (12) | C11d—C12d—H14d | 112 (3) |
C11b—C12b—H17b | 110 (2) | C11d—C12d—H15d | 110 (2) |
C11b—C12b—H18b | 111 (2) | C11d—C12d—H16d | 111 (2) |
H16b—C12b—H17b | 108 (2) | H14d—C12d—H15d | 108 (3) |
H16b—C12b—H18b | 108 (2) | H14d—C12d—H16d | 108 (3) |
H17b—C12b—H18b | 107.6 (8) | H15d—C12d—H16d | 108 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2a—H1a···O1a | 1.09 (3) | 2.46 (2) | 2.91 (2) | 102.9 (15) |
C5a—H4a···C4di | 1.10 (2) | 2.40 (2) | 3.15 (2) | 124.4 (11) |
C5a—H4a···C6di | 1.10 (2) | 2.12 (2) | 3.085 (19) | 146.0 (14) |
C5a—H4a···C7di | 1.10 (2) | 2.43 (2) | 3.09 (2) | 116.8 (12) |
C7a—H6a···C2di | 1.10 (3) | 2.40 (3) | 3.49 (2) | 167.6 (12) |
C7a—H7a···O3cii | 1.10 (2) | 2.37 (3) | 2.92 (2) | 109 (2) |
C7a—H7a···N2cii | 1.10 (2) | 2.18 (3) | 3.04 (2) | 132.3 (11) |
C7a—H7a···C8cii | 1.10 (2) | 2.36 (2) | 3.23 (2) | 135 (2) |
N2a—H9a···O1biii | 1.030 (17) | 1.86 (3) | 2.53 (3) | 119.6 (17) |
N2a—H9a···O3biii | 1.030 (17) | 2.161 (15) | 3.042 (12) | 142.4 (17) |
C9a—H10a···O1biii | 1.10 (2) | 1.91 (3) | 2.65 (3) | 120.4 (14) |
C10a—H12a···O3a | 1.106 (7) | 2.412 (12) | 3.102 (11) | 119.0 (10) |
C10a—H12a···C8a | 1.106 (7) | 2.318 (16) | 2.840 (14) | 106.6 (10) |
C2b—H1b···N1b | 1.09 (3) | 2.33 (4) | 2.84 (5) | 106.4 (18) |
C3b—H2b···O2aiv | 1.095 (14) | 2.134 (18) | 3.100 (17) | 145.5 (19) |
N1b—H8b···O3av | 1.02 (2) | 1.901 (14) | 2.841 (14) | 151.1 (10) |
N2b—H9b···O1av | 1.019 (19) | 1.848 (17) | 2.777 (17) | 150 (3) |
N2b—H9b···O3av | 1.019 (19) | 2.449 (9) | 3.139 (5) | 124.3 (14) |
C9b—H10b···O3b | 1.103 (15) | 2.37 (2) | 2.823 (19) | 102.4 (12) |
C2c—H1c···O3c | 1.09 (4) | 2.22 (4) | 2.90 (3) | 118 (2) |
C7c—H7c···N2avi | 1.10 (5) | 2.34 (3) | 3.07 (3) | 123 (2) |
N2c—H9c···O1d | 1.03 (3) | 1.861 (18) | 2.54 (2) | 120.4 (6) |
N2c—H9c···O3d | 1.03 (3) | 1.57 (2) | 2.47 (2) | 142.4 (11) |
C9c—H10c···O1d | 1.10 (3) | 1.99 (3) | 2.69 (3) | 117.5 (13) |
C2d—H1d···N1d | 1.09 (3) | 2.26 (4) | 2.81 (4) | 109.2 (19) |
C7d—H3d···C3avii | 1.104 (18) | 2.174 (18) | 3.196 (18) | 153 (2) |
C7d—H3d···C5avii | 1.104 (18) | 2.34 (2) | 3.09 (2) | 124 (2) |
N1d—H6d···O3cviii | 1.022 (9) | 2.35 (2) | 3.330 (19) | 161 (3) |
N2d—H7d···O1cviii | 1.02 (3) | 2.32 (2) | 3.28 (2) | 156 (3) |
C9d—H8d···O3d | 1.10 (3) | 2.33 (2) | 2.76 (2) | 100.7 (16) |
C10d—H10d···S1dix | 1.11 (3) | 2.43 (3) | 3.53 (3) | 173 (3) |
C10d—H10d···O2dix | 1.11 (3) | 1.75 (3) | 2.75 (3) | 148 (3) |
C10d—H11d···O2c | 1.10 (4) | 2.28 (3) | 2.97 (3) | 118.3 (16) |
C11d—H13d···N2d | 1.11 (4) | 2.26 (3) | 2.75 (3) | 104 (2) |
C12d—H15d···C3dix | 1.10 (4) | 2.02 (3) | 3.09 (4) | 164 (2) |
C12d—H15d···C5dix | 1.10 (4) | 2.46 (3) | 3.52 (3) | 161 (2) |
C3d—H17d···C12dx | 1.09 (3) | 2.42 (4) | 3.09 (4) | 118.5 (15) |
C5d—H18d···O2bxi | 1.09 (3) | 2.30 (4) | 2.97 (4) | 117.9 (11) |
Symmetry codes: (i) x−1, −y, z−1/2; (ii) x, −y, z−1/2; (iii) x−1, y−1, 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, z−1/2; (xi) x, y−1, z. |
(Tolbutamide_III)
N-[(butylamino)carbonyl]-4-methylbenzenesulfonamide
top
Crystal data top
C12H18N2O3S | Z = 4 |
Mr = 270.35 | F(000) = 576 |
Monoclinic, P21/n | Dx = 1.239 Mg m−3 |
a = 11.8094 (5) Å | Cu Kα radiation, λ = 1.54180 Å |
b = 9.0615 (4) Å | T = 298 K |
c = 13.9908 (9) Å | colourless |
β = 104.584 (2)° | ?, ? × ? × ? mm |
V = 1448.9 (2) Å3 | |
Data collection top
Bruker D8 diffractometer | Scan method: step |
Radiation source: sealed X-ray tube | 2θmin = 5°, 2θmax = 50°, 2θstep = 0.017° |
None monochromator | |
Refinement top
Refinement on Inet | 35 parameters |
Least-squares matrix: full with fixed elements per cycle | 0 restraints |
Rp = 0.070 | 0 constraints |
Rwp = 0.099 | H-atom parameters not refined |
Rexp = 0.042 | Weighting scheme based on measured s.u.'s 1/[Yi + σ(Yi)] |
RBragg = 0.053 | (Δ/σ)max = 0.01 |
χ2 = 5.712 | Background function: Chebychev of order 6 |
2695 data points | Preferred orientation correction: spherical harmonics order 4 |
Profile function: fundamental parameter | |
Crystal data top
C12H18N2O3S | β = 104.584 (2)° |
Mr = 270.35 | V = 1448.9 (2) Å3 |
Monoclinic, P21/n | Z = 4 |
a = 11.8094 (5) Å | Cu Kα radiation, λ = 1.54180 Å |
b = 9.0615 (4) Å | T = 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 = 0.070 | 2695 data points |
Rwp = 0.099 | 35 parameters |
Rexp = 0.042 | 0 restraints |
RBragg = 0.053 | H-atom parameters not refined |
χ2 = 5.712 | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | −1.3596 (5) | 0.8014 (9) | 0.3775 (2) | 0.096 (2) | |
O1 | −1.3372 (10) | 0.9064 (9) | 0.4594 (2) | 0.096 (2) | |
O2 | −1.33743 (18) | 0.6443 (10) | 0.39224 (16) | 0.096 (2) | |
N1 | −1.2759 (3) | 0.8557 (13) | 0.30232 (7) | 0.096 (2) | |
C1 | −1.5084 (4) | 0.8249 (5) | 0.3081 (6) | 0.096 (2) | |
C2 | −1.2566 (2) | 0.7879 (15) | 0.2155 (2) | 0.096 (2) | |
H1 | −1.2084 (5) | 0.9219 (15) | 0.3357 (2) | 0.096 (2) | |
C3 | −1.5840 (5) | 0.9087 (10) | 0.3482 (11) | 0.096 (2) | |
C4 | −1.54686 (15) | 0.7584 (5) | 0.2159 (3) | 0.096 (2) | |
O3 | −1.2776 (5) | 0.6571 (14) | 0.20260 (16) | 0.096 (2) | |
N2 | −1.2131 (3) | 0.8770 (17) | 0.1558 (4) | 0.096 (2) | |
C5 | −1.6998 (5) | 0.9248 (6) | 0.2950 (14) | 0.096 (2) | |
H2 | −1.5519 (7) | 0.9626 (17) | 0.4189 (13) | 0.096 (2) | |
C6 | −1.66298 (9) | 0.7758 (9) | 0.1638 (5) | 0.096 (2) | |
H3 | −1.48641 (3) | 0.6964 (9) | 0.18480 (15) | 0.096 (2) | |
C7 | −1.19464 (14) | 0.822 (2) | 0.06267 (11) | 0.096 (2) | |
H4 | −1.1817 (6) | 0.9769 (14) | 0.1818 (6) | 0.096 (2) | |
C8 | −1.7413 (2) | 0.8583 (3) | 0.2025 (11) | 0.096 (2) | |
H5 | −1.7586 (6) | 0.9910 (11) | 0.3256 (18) | 0.096 (2) | |
H6 | −1.69302 (9) | 0.7250 (16) | 0.0916 (3) | 0.096 (2) | |
C9 | −1.3013 (2) | 0.7418 (10) | −0.0012 (7) | 0.096 (2) | |
H7 | −1.1716 (12) | 0.917 (3) | 0.02264 (11) | 0.096 (2) | |
H8 | −1.1195 (5) | 0.748 (3) | 0.0801 (3) | 0.096 (2) | |
C10 | −1.86771 (17) | 0.8736 (7) | 0.1464 (13) | 0.096 (2) | |
C11 | −1.404392 (1) | 0.845729 (4) | −0.0423 (3) | 0.096 (2) | |
H9 | −1.3284 (3) | 0.6545 (17) | 0.0427 (14) | 0.096 (2) | |
H10 | −1.2751 (6) | 0.6872 (2) | −0.0621 (14) | 0.096 (2) | |
H11 | −1.9205 (2) | 0.7850 (4) | 0.1663 (10) | 0.096 (2) | |
H12 | −1.877757 (17) | 0.8674 (15) | 0.0667 (13) | 0.096 (2) | |
H13 | −1.9046 (3) | 0.9782 (4) | 0.1629 (19) | 0.096 (2) | |
C12 | −1.51654 (2) | 0.7642 (3) | −0.0942 (6) | 0.096 (2) | |
H14 | −1.42097 (19) | 0.9132 (19) | 0.0179 (11) | 0.096 (2) | |
H15 | −1.38032 (19) | 0.9231 (15) | −0.0942 (11) | 0.096 (2) | |
H16 | −1.58823 (9) | 0.8412 (6) | −0.1232 (2) | 0.096 (2) | |
H17 | −1.54478 (12) | 0.6890 (13) | −0.0435 (15) | 0.096 (2) | |
H18 | −1.50340 (12) | 0.699 (2) | −0.1562 (14) | 0.096 (2) | |
Geometric parameters (Å, º) top
S1—O1 | 1.461 (8) | C6—H6 | 1.085 (10) |
S1—O2 | 1.453 (12) | C7—C9 | 1.533 (11) |
S1—N1 | 1.688 (7) | C7—H7 | 1.09 (2) |
S1—C1 | 1.794 (7) | C7—H8 | 1.09 (2) |
N1—C2 | 1.430 (8) | C8—C10 | 1.508 (7) |
C1—C3 | 1.393 (12) | C9—C11 | 1.532 (6) |
C1—C4 | 1.392 (7) | C9—H9 | 1.097 (19) |
C2—O3 | 1.215 (18) | C9—H10 | 1.095 (19) |
C2—N2 | 1.353 (13) | C10—H11 | 1.095 (11) |
C3—C5 | 1.390 (10) | C10—H12 | 1.09 (3) |
C3—H2 | 1.08 (2) | C10—H13 | 1.092 (12) |
C4—C6 | 1.390 (3) | C11—C12 | 1.530 (3) |
C4—H3 | 1.083 (6) | C11—H14 | 1.098 (16) |
N2—C7 | 1.461 (10) | C11—H15 | 1.097 (15) |
C5—C8 | 1.40 (2) | C12—H16 | 1.093 (4) |
C5—H5 | 1.08 (2) | C12—H17 | 1.095 (18) |
C6—C8 | 1.400 (11) | C12—H18 | 1.09 (2) |
| | | |
O1—S1—O2 | 122.4 (4) | C9—C7—H8 | 109.8 (18) |
O1—S1—N1 | 106.3 (7) | H7—C7—H8 | 107.7 (13) |
O1—S1—C1 | 107.8 (6) | C5—C8—C6 | 118.4 (5) |
O2—S1—N1 | 105.1 (5) | C5—C8—C10 | 120.8 (9) |
O2—S1—C1 | 108.1 (4) | C6—C8—C10 | 120.8 (11) |
N1—S1—C1 | 106.0 (3) | C7—C9—C11 | 112.7 (9) |
S1—N1—C2 | 130.4 (8) | C7—C9—H9 | 109.2 (10) |
S1—C1—C3 | 119.1 (6) | C7—C9—H10 | 108.5 (5) |
S1—C1—C4 | 119.8 (4) | C11—C9—H9 | 109.7 (5) |
C3—C1—C4 | 121.1 (6) | C11—C9—H10 | 109.8 (8) |
N1—C2—O3 | 118.4 (7) | H9—C9—H10 | 106.8 (13) |
N1—C2—N2 | 115.8 (11) | C8—C10—H11 | 110.7 (10) |
O3—C2—N2 | 125.8 (7) | C8—C10—H12 | 111.5 (10) |
C1—C3—C5 | 119.0 (12) | C8—C10—H13 | 111.4 (10) |
C1—C3—H2 | 120.1 (8) | H11—C10—H12 | 107.4 (12) |
C5—C3—H2 | 120.8 (12) | H11—C10—H13 | 107.4 (12) |
C1—C4—C6 | 119.0 (5) | H12—C10—H13 | 108.3 (18) |
C1—C4—H3 | 120.2 (3) | C9—C11—C12 | 113.1 (3) |
C6—C4—H3 | 120.8 (5) | C9—C11—H14 | 109.5 (7) |
C2—N2—C7 | 120.9 (13) | C9—C11—H15 | 109.1 (5) |
C3—C5—C8 | 121.2 (10) | C12—C11—H14 | 109.4 (4) |
C3—C5—H5 | 119.2 (17) | C12—C11—H15 | 109.4 (6) |
C8—C5—H5 | 119.6 (11) | H14—C11—H15 | 106.1 (11) |
C4—C6—C8 | 121.2 (7) | C11—C12—H16 | 111.4 (3) |
C4—C6—H6 | 119.2 (6) | C11—C12—H17 | 111.2 (8) |
C8—C6—H6 | 119.6 (5) | C11—C12—H18 | 111.1 (4) |
N2—C7—C9 | 113.3 (5) | H16—C12—H17 | 107.6 (5) |
N2—C7—H7 | 107.7 (17) | H16—C12—H18 | 107.6 (9) |
N2—C7—H8 | 107.9 (5) | H17—C12—H18 | 107.6 (13) |
C9—C7—H7 | 110.3 (7) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 1.013 (12) | 2.194 (18) | 2.808 (17) | 117.4 (8) |
C4—H3···O3 | 1.083 (6) | 2.441 (6) | 3.360 (7) | 141.9 (4) |
N2—H4···O2i | 1.011 (18) | 1.882 (14) | 2.622 (17) | 127.4 (8) |
N2—H4···O3i | 1.011 (18) | 2.430 (14) | 3.239 (16) | 136.5 (7) |
C6—H6···O1ii | 1.085 (10) | 2.480 (10) | 3.489 (9) | 154.1 (4) |
C7—H7···O2i | 1.09 (2) | 2.37 (2) | 2.99 (2) | 114.1 (9) |
C9—H9···O3 | 1.097 (19) | 2.165 (19) | 2.898 (11) | 121.8 (11) |
Symmetry codes: (i) −x−5/2, y+1/2, −z+1/2; (ii) x−1/2, −y+3/2, z−1/2. |
(Glycine) Aminoethanoic acid
top
Crystal data top
C2H5NO2 | Z = 4 |
Mr = 75.07 | F(000) = 160 |
Monoclinic, P21/c | Dx = 1.608 Mg m−3 |
a = 5.10422 (8) Å | Cu Kα radiation, λ = 1.54180 Å |
b = 11.97177 (17) Å | T = 298 K |
c = 5.93652 (9) Å | colourless |
β = 121.2642 (8)° | ?, ? × ? × ? mm |
V = 310.08 (1) Å3 | |
Data collection top
Bruker D8 diffractometer | Scan method: step |
Radiation source: sealed X-ray tube | 2θmin = 7.5°, 2θmax = 130°, 2θstep = 0.017° |
None monochromator | |
Refinement top
Refinement on Inet | 25 parameters |
Least-squares matrix: full with fixed elements per cycle | 0 restraints |
Rp = 0.079 | 0 constraints |
Rwp = 0.113 | H-atom parameters not refined |
Rexp = 0.012 | Weighting scheme based on measured s.u.'s 1/[Yi + σ(Yi)] |
RBragg = 0.033 | (Δ/σ)max = 0.01 |
χ2 = 93.316 | Background function: Chebychev of order 3 |
7333 data points | Preferred orientation correction: March-Dollase (0 1 0)(1 0 2) |
Profile function: fundamental parameter | |
Crystal data top
C2H5NO2 | β = 121.2642 (8)° |
Mr = 75.07 | V = 310.08 (1) Å3 |
Monoclinic, P21/c | Z = 4 |
a = 5.10422 (8) Å | Cu Kα radiation, λ = 1.54180 Å |
b = 11.97177 (17) Å | T = 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 = 0.079 | 7333 data points |
Rwp = 0.113 | 25 parameters |
Rexp = 0.012 | 0 restraints |
RBragg = 0.033 | H-atom parameters not refined |
χ2 = 93.316 | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.2773 (8) | 0.8486 (2) | 0.2168 (5) | 0.0312 (5) | |
C2 | 0.0136 (4) | 0.87285 (7) | −0.0576 (3) | 0.0312 (5) | |
H1 | 0.641 (4) | 0.8829 (18) | 0.146 (4) | 0.0312 (5) | |
H2 | 0.533 (2) | 0.9932 (3) | 0.244 (6) | 0.0312 (5) | |
H3 | 0.751 (2) | 0.896 (2) | 0.4571 (18) | 0.0312 (5) | |
H4 | 0.2160 (10) | 0.8788 (5) | 0.3611 (6) | 0.0312 (5) | |
H5 | 0.3194 (12) | 0.7570 (2) | 0.2410 (9) | 0.0312 (5) | |
N1 | 0.5766 (9) | 0.91038 (19) | 0.2706 (4) | 0.0312 (5) | |
O1 | 0.0650 (5) | 0.9062 (2) | −0.2321 (5) | 0.0312 (5) | |
O2 | −0.2579 (6) | 0.8587 (2) | −0.1128 (4) | 0.0312 (5) | |
Geometric parameters (Å, º) top
C1—C2 | 1.508 (3) | C2—O2 | 1.259 (3) |
C1—H4 | 1.114 (6) | H1—N1 | 1.01 (3) |
C1—H5 | 1.112 (3) | H2—N1 | 1.010 (5) |
C1—N1 | 1.574 (6) | H3—N1 | 1.011 (9) |
C2—O1 | 1.259 (4) | | |
| | | |
C2—C1—H4 | 108.6 (3) | O1—C2—O2 | 119.99 (16) |
C2—C1—H5 | 109.5 (3) | C1—N1—H1 | 110.5 (11) |
C2—C1—N1 | 110.9 (2) | C1—N1—H2 | 108.6 (9) |
H4—C1—H5 | 109.5 (5) | C1—N1—H3 | 110.7 (10) |
H4—C1—N1 | 108.8 (3) | H1—N1—H2 | 109 (2) |
H5—C1—N1 | 109.6 (4) | H1—N1—H3 | 108.4 (13) |
C1—C2—O1 | 120.0 (2) | H2—N1—H3 | 109.3 (19) |
C1—C2—O2 | 120.0 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 1.01 (3) | 1.88 (3) | 2.876 (5) | 169.4 (18) |
N1—H2···O1ii | 1.010 (5) | 2.410 (19) | 2.942 (5) | 112.0 (14) |
N1—H2···O2iii | 1.010 (5) | 2.142 (7) | 3.096 (4) | 156.7 (9) |
N1—H3···C2iv | 1.011 (9) | 2.483 (10) | 3.442 (2) | 158.1 (10) |
N1—H3···O1iv | 1.011 (9) | 1.709 (8) | 2.701 (3) | 166 (2) |
C1—H5···O1v | 1.112 (3) | 2.397 (5) | 3.303 (4) | 137.5 (5) |
C1—H5···O2vi | 1.112 (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
C8H9NO2 | Z = 4 |
Mr = 151.17 | F(000) = 320 |
Monoclinic, P21/n | Dx = 1.297 Mg m−3 |
a = 11.7144 (5) Å | Cu Kα radiation, λ = 1.54180 Å |
b = 9.3854 (2) Å | T = 298 K |
c = 7.10166 (4) Å | colourless |
β = 82.58786 (2)° | ?, ? × ? × ? mm |
V = 774.27 (1) Å3 | |
Data collection top
Bruker D8 diffractometer | Scan method: step |
Radiation source: sealed X-ray tube | 2θmin = 7.5°, 2θmax = 130°, 2θstep = 0.017° |
None monochromator | |
Refinement top
Refinement on Inet | 25 parameters |
Least-squares matrix: full with fixed elements per cycle | 0 restraints |
Rp = 0.141 | 5 constraints |
Rwp = 0.188 | H-atom parameters not refined |
Rexp = 0.011 | Weighting scheme based on measured s.u.'s 1/[Yi + σ(Yi)] |
RBragg = 0.080 | (Δ/σ)max = 0.01 |
χ2 = 295.840 | Background function: Chebychev of order 3 |
7333 data points | Preferred orientation correction: Spherical Harmonics Order 2 |
Profile function: fundamental parameter | |
Crystal data top
C8H9NO2 | β = 82.58786 (2)° |
Mr = 151.17 | V = 774.27 (1) Å3 |
Monoclinic, P21/n | Z = 4 |
a = 11.7144 (5) Å | Cu Kα radiation, λ = 1.54180 Å |
b = 9.3854 (2) Å | T = 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 = 0.141 | 7333 data points |
Rwp = 0.188 | 25 parameters |
Rexp = 0.011 | 0 restraints |
RBragg = 0.080 | H-atom parameters not refined |
χ2 = 295.840 | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.0701 (4) | −0.14232 (12) | 0.5691 (5) | 0.0409 (5) | |
C2 | 0.0009 (5) | −0.14126 (6) | 0.7482 (3) | 0.0409 (5) | |
C3 | 0.0408 (3) | −0.2331 (3) | 0.4233 (5) | 0.0409 (5) | |
C4 | −0.0971 (4) | −0.23059 (14) | 0.7813 (3) | 0.0409 (5) | |
C5 | −0.05720 (16) | −0.3225 (3) | 0.4563 (5) | 0.0409 (5) | |
C6 | −0.1262 (2) | −0.3213 (3) | 0.6352 (4) | 0.0409 (5) | |
C7 | 0.2227 (4) | 0.0036 (3) | 0.6776 (5) | 0.0409 (5) | |
C8 | 0.3325 (4) | 0.0876 (3) | 0.6302 (6) | 0.0409 (5) | |
N1 | 0.1683 (5) | −0.053863 (14) | 0.5337 (5) | 0.0409 (5) | |
O1 | −0.22024 (17) | −0.4070 (4) | 0.6670 (3) | 0.0409 (5) | |
O2 | 0.1824 (3) | −0.0136 (5) | 0.8416 (5) | 0.0409 (5) | |
H1 | 0.0235 (6) | −0.07025 (6) | 0.8630 (3) | 0.0409 (5) | |
H2 | 0.09483 (18) | −0.2342 (3) | 0.2827 (6) | 0.0409 (5) | |
H3 | −0.1512 (5) | −0.22957 (10) | 0.92181 (18) | 0.0409 (5) | |
H4 | −0.07994 (4) | −0.3936 (5) | 0.3417 (5) | 0.0409 (5) | |
H5 | −0.24099 (6) | −0.4718 (5) | 0.5626 (3) | 0.0409 (5) | |
H6 | 0.2026 (6) | −0.0295 (3) | 0.3928 (5) | 0.0409 (5) | |
H7 | 0.4076 (4) | 0.0147 (3) | 0.6253 (3) | 0.0409 (5) | |
H8 | 0.3327 (5) | 0.13970 (4) | 0.4897 (8) | 0.0409 (5) | |
H9 | 0.3381 (3) | 0.1702 (4) | 0.7408 (8) | 0.0409 (5) | |
Geometric parameters (Å, º) top
C1—C2 | 1.417 (5) | C5—H4 | 1.111 (5) |
C1—C3 | 1.417 (4) | C6—O1 | 1.359 (4) |
C1—N1 | 1.414 (6) | C7—C8 | 1.509 (6) |
C2—C4 | 1.416 (6) | C7—N1 | 1.382 (6) |
C2—H1 | 1.111 (4) | C7—O2 | 1.210 (5) |
C3—C5 | 1.417 (4) | C8—H7 | 1.111 (6) |
C3—H2 | 1.111 (5) | C8—H8 | 1.111 (7) |
C4—C6 | 1.417 (3) | C8—H9 | 1.112 (6) |
C4—H3 | 1.111 (4) | N1—H6 | 1.054 (5) |
C5—C6 | 1.415 (4) | O1—H5 | 1.012 (4) |
| | | |
C2—C1—C3 | 119.7 (3) | C4—C6—O1 | 120.0 (2) |
C2—C1—N1 | 120.9 (3) | C5—C6—O1 | 120.1 (2) |
C3—C1—N1 | 119.4 (3) | C8—C7—N1 | 120.0 (3) |
C1—C2—C4 | 120.2 (2) | C8—C7—O2 | 120.0 (4) |
C1—C2—H1 | 120.0 (5) | N1—C7—O2 | 120.0 (4) |
C4—C2—H1 | 119.9 (4) | C7—C8—H7 | 109.5 (3) |
C1—C3—C5 | 120.2 (3) | C7—C8—H8 | 109.5 (5) |
C1—C3—H2 | 119.9 (3) | C7—C8—H9 | 109.5 (4) |
C5—C3—H2 | 119.9 (3) | H7—C8—H8 | 109.4 (4) |
C2—C4—C6 | 120.0 (2) | H7—C8—H9 | 109.4 (5) |
C2—C4—H3 | 120.0 (3) | H8—C8—H9 | 109.5 (4) |
C6—C4—H3 | 120.0 (4) | C1—N1—C7 | 122.7 (3) |
C3—C5—C6 | 120.0 (3) | C1—N1—H6 | 119.9 (5) |
C3—C5—H4 | 120.0 (3) | C7—N1—H6 | 117.5 (5) |
C6—C5—H4 | 120.0 (3) | C6—O1—H5 | 120.1 (2) |
C4—C6—C5 | 119.9 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H1···O2 | 1.111 (4) | 1.923 (8) | 2.600 (6) | 115.3 (5) |
O1—H5···O2i | 1.012 (4) | 1.911 (4) | 2.806 (5) | 145.8 (4) |
N1—H6···O1ii | 1.054 (5) | 1.836 (5) | 2.784 (4) | 147.5 (3) |
Symmetry codes: (i) x−1/2, −y−1/2, z−1/2; (ii) x+1/2, −y−1/2, z−1/2. |
(Lactose_monohydrate) /b-
D-galactopyranosyl-(1,4)-D-glucose monhydrate
top
Crystal data top
C12H24O12 | Z = 2 |
Mr = 360.31 | F(000) = 384 |
Monoclinic, P21 | Dx = 1.540 Mg m−3 |
a = 7.7721 (4) Å | Cu Kα radiation, λ = 1.54180 Å |
b = 21.58192 (17) Å | T = 298 K |
c = 4.8172 (3) Å | colourless |
β = 74.0609 (12)° | ?, ? × ? × ? mm |
V = 776.96 (9) Å3 | |
Data collection top
Bruker D8 diffractometer | Scan method: step |
Radiation source: sealed X-ray tube | 2θmin = 7.5°, 2θmax = 130°, 2θstep = 0.017° |
None monochromator | |
Refinement top
Refinement on Inet | 29 parameters |
Least-squares matrix: full with fixed elements per cycle | 0 restraints |
Rp = 0.183 | 3 constraints |
Rwp = 0.274 | H-atom parameters not refined |
Rexp = 0.011 | Weighting scheme based on measured s.u.'s 1/[Yi + σ(Yi)] |
RBragg = 0.105 | (Δ/σ)max = 0.01 |
χ2 = 576.000 | Background function: Chebychev of order 3 |
7333 data points | Preferred orientation correction: Spherical Harmonics Order 4 |
Profile function: fundamental parameter | |
Crystal data top
C12H24O12 | β = 74.0609 (12)° |
Mr = 360.31 | V = 776.96 (9) Å3 |
Monoclinic, P21 | Z = 2 |
a = 7.7721 (4) Å | Cu Kα radiation, λ = 1.54180 Å |
b = 21.58192 (17) Å | T = 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 = 0.183 | 7333 data points |
Rwp = 0.274 | 29 parameters |
Rexp = 0.011 | 0 restraints |
RBragg = 0.105 | H-atom parameters not refined |
χ2 = 576.000 | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.342 (3) | 0.5844 (2) | 0.872 (7) | 0.0477 (19) | |
C2 | 0.543 (4) | 0.57524 (9) | 0.824 (3) | 0.0477 (19) | |
C3 | 0.786 (3) | 0.5102 (3) | 0.5782 (9) | 0.0477 (19) | |
C4 | 0.7846 (15) | 0.4006 (3) | 0.4832 (5) | 0.0477 (19) | |
C5 | 0.5897 (11) | 0.3833 (6) | 0.501 (2) | 0.0477 (19) | |
C6 | 0.5542 (3) | 0.3147 (7) | 0.578 (3) | 0.0477 (19) | |
C7 | 0.6953 (6) | 0.2734 (4) | 0.377 (3) | 0.0477 (19) | |
C8 | 0.9113 (5) | 0.35487 (5) | 0.2796 (5) | 0.0477 (19) | |
C9 | 1.1074 (9) | 0.3676 (2) | 0.2704 (10) | 0.0477 (19) | |
C10 | 0.911 (2) | 0.5660 (5) | 0.472 (4) | 0.0477 (19) | |
C11 | 0.850 (3) | 0.6217 (5) | 0.673 (4) | 0.0477 (19) | |
C12 | 0.650 (2) | 0.63473 (19) | 0.71904 (12) | 0.0477 (19) | |
O1 | 0.2967 (8) | 0.5790 (2) | 0.607 (9) | 0.0477 (19) | |
O2 | 0.603 (3) | 0.528071 (7) | 0.609 (3) | 0.0477 (19) | |
O3 | 0.825 (2) | 0.4619 (2) | 0.3673 (3) | 0.0477 (19) | |
O4 | 0.466 (2) | 0.4193 (8) | 0.719 (2) | 0.0477 (19) | |
O5 | 0.37701 (13) | 0.2996 (9) | 0.560 (4) | 0.0477 (19) | |
O6 | 0.6718 (13) | 0.2751 (3) | 0.094 (3) | 0.0477 (19) | |
O7 | 0.87094 (15) | 0.29176 (13) | 0.3714 (14) | 0.0477 (19) | |
O8 | 1.22360 (5) | 0.3315 (5) | 0.0466 (11) | 0.0477 (19) | |
O9 | 1.095 (3) | 0.5527 (8) | 0.460 (8) | 0.0477 (19) | |
O10 | 0.9545 (15) | 0.6746 (6) | 0.547 (7) | 0.0477 (19) | |
O11 | 0.6272 (4) | 0.65513 (10) | 0.4462 (15) | 0.0477 (19) | |
H1 | 0.1673 (7) | 0.5836 (5) | 0.651 (12) | 0.0477 (19) | |
H2 | 0.302 (3) | 0.6305 (3) | 0.963 (8) | 0.0477 (19) | |
H3 | 0.265 (5) | 0.5506 (4) | 1.026 (8) | 0.0477 (19) | |
H4 | 0.567 (6) | 0.5601 (3) | 1.0284 (18) | 0.0477 (19) | |
H5 | 0.798 (5) | 0.4936 (5) | 0.7866 (18) | 0.0477 (19) | |
H6 | 0.804 (2) | 0.3973 (3) | 0.6997 (2) | 0.0477 (19) | |
H7 | 0.5597 (7) | 0.3945 (6) | 0.297 (2) | 0.0477 (19) | |
H8 | 0.3494 (16) | 0.3995 (10) | 0.743 (3) | 0.0477 (19) | |
H9 | 0.5558 (8) | 0.3075 (7) | 0.802 (3) | 0.0477 (19) | |
H10 | 0.3897 (8) | 0.2920 (8) | 0.355 (5) | 0.0477 (19) | |
H11 | 0.6751 (11) | 0.2254 (4) | 0.451 (3) | 0.0477 (19) | |
H12 | 0.7589 (19) | 0.24540 (18) | −0.015 (3) | 0.0477 (19) | |
H13 | 0.90001 (3) | 0.359720 (4) | 0.0583 (7) | 0.0477 (19) | |
H14 | 1.1333 (12) | 0.3545 (2) | 0.4748 (12) | 0.0477 (19) | |
H15 | 1.1427 (14) | 0.4163 (3) | 0.2243 (18) | 0.0477 (19) | |
H16 | 1.3444 (2) | 0.3384 (7) | 0.061 (2) | 0.0477 (19) | |
H17 | 0.91146 (9) | 0.5780 (3) | 0.251 (3) | 0.0477 (19) | |
H18 | 1.154 (2) | 0.5932 (9) | 0.442 (10) | 0.0477 (19) | |
H19 | 0.878 (5) | 0.6132 (8) | 0.881 (6) | 0.0477 (19) | |
H20 | 0.88556 (2) | 0.6952 (4) | 0.431 (5) | 0.0477 (19) | |
H21 | 0.608 (3) | 0.6731 (3) | 0.871166 (1) | 0.0477 (19) | |
H22 | 0.6036 (9) | 0.6182 (2) | 0.345 (3) | 0.0477 (19) | |
O1w | 0.760 (2) | 0.1719 (2) | 0.487 (4) | 0.0477 (19) | |
H1w | 0.724 (2) | 0.1719 (2) | 0.695 (4) | 0.0477 (19) | |
H2w | 0.649 (2) | 0.1719 (2) | 0.436 (4) | 0.0477 (19) | |
Geometric parameters (Å, º) top
C1—C2 | 1.53 (4) | C8—O7 | 1.440 (3) |
C1—O1 | 1.42 (6) | C8—H13 | 1.098 (4) |
C1—H2 | 1.10 (2) | C9—O8 | 1.432 (8) |
C1—H3 | 1.10 (3) | C9—H14 | 1.095 (9) |
C2—C12 | 1.536 (16) | C9—H15 | 1.094 (8) |
C2—O2 | 1.434 (14) | C10—C11 | 1.534 (19) |
C2—H4 | 1.10 (3) | C10—O9 | 1.44 (3) |
C3—C10 | 1.547 (18) | C10—H17 | 1.10 (3) |
C3—O2 | 1.44 (3) | C11—C12 | 1.53 (3) |
C3—O3 | 1.431 (6) | C11—O10 | 1.44 (2) |
C3—H5 | 1.095 (19) | C11—H19 | 1.10 (4) |
C4—C5 | 1.539 (15) | C12—O11 | 1.442 (10) |
C4—C8 | 1.541 (7) | C12—H21 | 1.096 (7) |
C4—O3 | 1.435 (8) | O1—H1 | 0.974 (9) |
C4—H6 | 1.096 (8) | O4—H8 | 0.98 (2) |
C5—C6 | 1.53 (2) | O5—H10 | 0.98 (3) |
C5—O4 | 1.440 (16) | O6—H12 | 0.974 (13) |
C5—H7 | 1.097 (15) | O8—H16 | 0.972 (5) |
C6—C7 | 1.533 (14) | O9—H18 | 0.98 (3) |
C6—O5 | 1.439 (10) | O10—H20 | 0.98 (3) |
C6—H9 | 1.10 (2) | O11—H22 | 0.978 (10) |
C7—O6 | 1.42 (2) | H1—H18i | 1.06 (7) |
C7—O7 | 1.415 (7) | O1w—H1w | 0.96 (3) |
C7—H11 | 1.094 (13) | O1w—H2w | 0.96 (3) |
C8—C9 | 1.537 (8) | | |
| | | |
C2—C1—O1 | 110.4 (19) | C4—C8—O7 | 111.3 (3) |
C2—C1—H2 | 110 (2) | C4—C8—H13 | 110.5 (3) |
C2—C1—H3 | 111 (3) | C9—C8—O7 | 108.0 (3) |
O1—C1—H2 | 109 (3) | C9—C8—H13 | 107.3 (3) |
O1—C1—H3 | 109 (3) | O7—C8—H13 | 108.6 (3) |
H2—C1—H3 | 107 (3) | C8—C9—O8 | 109.9 (4) |
C1—C2—C12 | 112.2 (11) | C8—C9—H14 | 110.7 (6) |
C1—C2—O2 | 108.4 (19) | C8—C9—H15 | 111.6 (7) |
C1—C2—H4 | 108 (3) | O8—C9—H14 | 107.6 (6) |
C12—C2—O2 | 108.5 (12) | O8—C9—H15 | 107.4 (7) |
C12—C2—H4 | 110 (2) | H14—C9—H15 | 109.4 (8) |
O2—C2—H4 | 109.6 (13) | C3—C10—C11 | 110.0 (12) |
C10—C3—O2 | 110.0 (9) | C3—C10—O9 | 112.8 (13) |
C10—C3—O3 | 109.9 (11) | C3—C10—H17 | 109.6 (14) |
C10—C3—H5 | 111 (2) | C11—C10—O9 | 108.6 (18) |
O2—C3—O3 | 106.6 (15) | C11—C10—H17 | 110.1 (11) |
O2—C3—H5 | 109 (2) | O9—C10—H17 | 105.7 (18) |
O3—C3—H5 | 110.9 (10) | C10—C11—C12 | 111.4 (15) |
C5—C4—C8 | 109.1 (6) | C10—C11—O10 | 108.2 (15) |
C5—C4—O3 | 110.7 (10) | C10—C11—H19 | 109.6 (17) |
C5—C4—H6 | 108.8 (10) | C12—C11—O10 | 110.5 (12) |
C8—C4—O3 | 107.9 (5) | C12—C11—H19 | 110 (2) |
C8—C4—H6 | 109.5 (9) | O10—C11—H19 | 107 (2) |
O3—C4—H6 | 110.9 (7) | C2—C12—C11 | 109.1 (12) |
C4—C5—C6 | 110.9 (7) | C2—C12—O11 | 111.5 (12) |
C4—C5—O4 | 111.1 (10) | C2—C12—H21 | 112.1 (11) |
C4—C5—H7 | 110.2 (7) | C11—C12—O11 | 107.2 (10) |
C6—C5—O4 | 107.8 (9) | C11—C12—H21 | 110.0 (18) |
C6—C5—H7 | 111.1 (12) | O11—C12—H21 | 106.8 (9) |
O4—C5—H7 | 105.6 (11) | C1—O1—H1 | 107 (5) |
C5—C6—C7 | 111.1 (7) | C2—O2—C3 | 112.3 (17) |
C5—C6—O5 | 108.5 (11) | C3—O3—C4 | 114.5 (3) |
C5—C6—H9 | 109.0 (14) | C5—O4—H8 | 105.2 (17) |
C7—C6—O5 | 111.2 (12) | C6—O5—H10 | 105.2 (10) |
C7—C6—H9 | 109.8 (11) | C7—O6—H12 | 104.2 (14) |
O5—C6—H9 | 107.1 (11) | C7—O7—C8 | 113.5 (5) |
C6—C7—O6 | 109.4 (8) | C9—O8—H16 | 106.6 (10) |
C6—C7—O7 | 111.5 (8) | C10—O9—H18 | 105 (2) |
C6—C7—H11 | 109.2 (10) | C11—O10—H20 | 105.4 (16) |
O6—C7—O7 | 110.7 (8) | C12—O11—H22 | 107.1 (8) |
O6—C7—H11 | 107.2 (12) | O1—H1—H18i | 100 (5) |
O7—C7—H11 | 108.8 (9) | O9—H18—H1ii | 85 (4) |
C4—C8—C9 | 111.1 (5) | H1w—O1w—H2w | 105 (2) |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···C10i | 0.974 (9) | 2.40 (4) | 3.25 (3) | 144 (5) |
O1—H1···O9i | 0.974 (9) | 1.38 (6) | 1.98 (4) | 113 (4) |
O9i—H1···C1 | 1.38 (6) | 1.94 (5) | 3.20 (5) | 148.0 (11) |
O9i—H1···O1 | 1.38 (6) | 0.974 (9) | 1.98 (4) | 113 (4) |
O9i—H1···O1wiii | 1.38 (6) | 2.047 (18) | 2.85 (2) | 111 (3) |
C1—H3···O9iv | 1.10 (3) | 2.14 (5) | 3.03 (4) | 136.1 (19) |
O4—H8···O5 | 0.98 (2) | 2.32 (3) | 2.83 (3) | 112.1 (15) |
O4—H8···O8iv | 0.98 (2) | 2.114 (19) | 2.828 (16) | 128.5 (16) |
C6—H9···O6v | 1.10 (2) | 1.99 (2) | 3.00 (2) | 151.2 (8) |
O5—H10···O6 | 0.98 (3) | 2.238 (13) | 2.784 (17) | 114.0 (9) |
O5—H10···O8i | 0.98 (3) | 2.38 (2) | 3.11 (2) | 130.5 (12) |
C7—H11···O1w | 1.094 (13) | 1.362 (14) | 2.341 (12) | 144.5 (9) |
O1w—H11···C6 | 1.362 (14) | 2.157 (16) | 3.443 (16) | 155.4 (14) |
O1w—H11···C7 | 1.362 (14) | 1.094 (13) | 2.341 (12) | 144.5 (9) |
O1w—H11···O6 | 1.362 (14) | 2.03 (2) | 3.119 (19) | 132.3 (12) |
O1w—H11···O7 | 1.362 (14) | 2.048 (9) | 2.737 (7) | 105.0 (8) |
C9—H14···O5ii | 1.095 (9) | 2.364 (15) | 3.179 (17) | 129.8 (7) |
O8—H16···O4vi | 0.972 (5) | 2.411 (19) | 2.828 (16) | 105.3 (10) |
O9—H18···O1ii | 0.98 (3) | 1.57 (5) | 1.98 (4) | 99 (3) |
O9—H18···O10 | 0.98 (3) | 2.30 (2) | 2.83 (2) | 113.0 (18) |
O9—H18···O1wvii | 0.98 (3) | 1.89 (2) | 2.85 (2) | 165 (4) |
O10—H20···O11 | 0.98 (3) | 2.169 (7) | 2.749 (19) | 116.4 (11) |
O11—H22···O2 | 0.978 (10) | 2.325 (12) | 2.843 (5) | 112.2 (11) |
O1w—H2w···C1viii | 0.96 (3) | 2.39 (3) | 2.82 (3) | 106.6 (11) |
O1w—H2w···O11viii | 0.96 (3) | 2.094 (15) | 2.956 (16) | 148.6 (18) |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x+1, y+1/2, −z+1; (iv) x−1, y, z+1; (v) x, y, z+1; (vi) x+1, y, z−1; (vii) −x+2, y+1/2, −z+1; (viii) −x+1, y−1/2, −z+1. |
Experimental details
| (Al2O3_BTEM) | (CaF2_BTEM) | (ZnO_BTEM) | (Tolbutamide_IL) |
Crystal data |
Chemical formula | Al2O3 | CaF2 | ZnO | C12H18N2O3S |
Mr | 101.96 | 78.08 | 81.39 | 270.35 |
Crystal system, space group | Hexagonal, R3c | Cubic, Fm3m | Hexagonal, P63mc | Orthorhombic, Pna21 |
Temperature (K) | 298 | 298 | 298 | 298 |
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, 120 | 90, 90, 90 | 90, 90, 120 | 90, 90, 90 |
V (Å3) | 254.69 (1) | 163.06 (1) | 47.60 (1) | 1452.33 (14) |
Z | 6 | 4 | 2 | 4 |
Radiation type | Cu Kα, λ = 1.541802 Å | Cu Kα, λ = 1.541802 Å | Cu Kα, λ = 1.541802 Å | Cu Kα, λ = 1.54180 Å |
Specimen shape, size (mm) | ?, ? × ? × ? | ?, ? × ? × ? | ?, ? × ? × ? | ?, ? × ? × ? |
|
Data collection |
Diffractometer | Philips 3020 diffractometer | Philips 3020 diffractometer | Philips 3020 diffractometer | Bruker D8 diffractometer |
Specimen mounting | ? | ? | ? | ? |
Data collection mode | ? | ? | ? | ? |
Scan method | Step | Step | Step | Step |
2θ values (°) | 2θmin = 5 2θmax = 150 2θstep = 0.02 | 2θmin = 5 2θmax = 150 2θstep = 0.02 | 2θmin = 5 2θmax = 150 2θstep = 0.02 | 2θmin = 5 2θmax = 50 2θstep = 0.017 |
|
Refinement |
R factors and goodness of fit | Rp = 0.118, Rwp = 0.236, Rexp = 0.247, RBragg = 0.018, χ2 = 0.009 | Rp = 0.127, Rwp = 0.256, Rexp = 0.387, RBragg = 0.015, χ2 = 0.436 | Rp = 0.079, Rwp = 0.149, Rexp = 0.337, RBragg = 0.018, χ2 = 0.194 | Rp = 0.083, Rwp = 0.122, Rexp = 0.042, RBragg = 0.054, χ2 = 8.294 |
No. of data points | 7250 | 7250 | 7250 | 2695 |
No. of parameters | 12 | 12 | 12 | 22 |
H-atom treatment | – | – | – | H-atom parameters not refined |
| (Tolbutamide_II) | (Tolbutamide_III) | (Glycine) | (paracetamol) |
Crystal data |
Chemical formula | C12H18N2O3S | C12H18N2O3S | C2H5NO2 | C8H9NO2 |
Mr | 270.35 | 270.35 | 75.07 | 151.17 |
Crystal system, space group | Monoclinic, Pc | Monoclinic, P21/n | Monoclinic, P21/c | Monoclinic, P21/n |
Temperature (K) | 298 | 298 | 298 | 298 |
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), 90 | 90, 104.584 (2), 90 | 90, 121.2642 (8), 90 | 90, 82.58786 (2), 90 |
V (Å3) | 2840.3 (9) | 1448.9 (2) | 310.08 (1) | 774.27 (1) |
Z | 8 | 4 | 4 | 4 |
Radiation type | Cu Kα, λ = 1.54180 Å | Cu Kα, λ = 1.54180 Å | Cu Kα, λ = 1.54180 Å | Cu Kα, λ = 1.54180 Å |
Specimen shape, size (mm) | ?, ? × ? × ? | ?, ? × ? × ? | ?, ? × ? × ? | ?, ? × ? × ? |
|
Data collection |
Diffractometer | Bruker D8 diffractometer | Bruker D8 diffractometer | Bruker D8 diffractometer | Bruker D8 diffractometer |
Specimen mounting | ? | ? | ? | ? |
Data collection mode | ? | ? | ? | ? |
Scan method | Step | Step | Step | Step |
2θ values (°) | 2θmin = 5 2θmax = 50 2θstep = 0.017 | 2θmin = 5 2θmax = 50 2θstep = 0.017 | 2θmin = 7.5 2θmax = 130 2θstep = 0.017 | 2θmin = 7.5 2θmax = 130 2θstep = 0.017 |
|
Refinement |
R factors and goodness of fit | Rp = 0.102, Rwp = 0.137, Rexp = 0.042, RBragg = 0.047, χ2 = 10.562 | Rp = 0.070, Rwp = 0.099, Rexp = 0.042, RBragg = 0.053, χ2 = 5.712 | Rp = 0.079, Rwp = 0.113, Rexp = 0.012, RBragg = 0.033, χ2 = 93.316 | Rp = 0.141, Rwp = 0.188, Rexp = 0.011, RBragg = 0.080, χ2 = 295.840 |
No. of data points | 2695 | 2695 | 7333 | 7333 |
No. of parameters | 59 | 35 | 25 | 25 |
H-atom treatment | H-atom parameters not refined | H-atom parameters not refined | H-atom parameters not refined | H-atom parameters not refined |
| (Lactose_monohydrate) |
Crystal data |
Chemical formula | C12H24O12 |
Mr | 360.31 |
Crystal system, space group | Monoclinic, 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 |
V (Å3) | 776.96 (9) |
Z | 2 |
Radiation type | Cu Kα, λ = 1.54180 Å |
Specimen shape, size (mm) | ?, ? × ? × ? |
|
Data collection |
Diffractometer | Bruker D8 diffractometer |
Specimen mounting | ? |
Data collection mode | ? |
Scan method | Step |
2θ values (°) | 2θmin = 7.5 2θmax = 130 2θstep = 0.017 |
|
Refinement |
R factors and goodness of fit | Rp = 0.183, Rwp = 0.274, Rexp = 0.011, RBragg = 0.105, χ2 = 576.000 |
No. of data points | 7333 |
No. of parameters | 29 |
H-atom treatment | H-atom parameters not refined |
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