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Apremilast (AP) {systematic name: (S)-2-[1-(3-eth­oxy-4-meth­oxy­phen­yl)-2-(methyl­sulfon­yl)eth­yl]-4-acetamido­isoindoline-1,3-dione} is an inhibitor of phospho­dieasterase-4 (PDE4) and is indicated for the treatment of adult patients with active psoriatic arthritis. The ability of AP to form solvates has been investigated and three solvatomorphs of AP, namely, the AP ethyl acetate hemisolvate, C22H24N2O7S·0.5C4H8O2, the AP toluene hemisolvate, C22H24N2O7S·0.5C7H8, and the AP di­chloro­methane monosolvate, C22H24N2O7S·CH2Cl2, were obtained. The three AP solvatomorphs were characterized by X-ray powder diffraction, thermogravimetric analysis and differential scanning calorimetry. Single-crystal X-ray diffraction was used to analyze the structures, crystal symmetry, packing modes, stoichiometry and hydrogen-bonding inter­actions of the solvatomorphs. In addition, dissolution analyses were performed to study the dissolution rates of different AP solvatomorph tablets in vitro and to make comparisons with commercial apremilast tablets (produced by Celgene); all three solvatomorphs showed similar dissolution rates and similar values of the similarity factor f2 in a comparison of their dissolution profiles.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617002984/fm3048sup1.cif
Contains datablocks global, 2, 3, 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617002984/fm30481sup5.hkl
Contains datablock 1

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617002984/fm30481sup2.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617002984/fm30482sup3.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617002984/fm30483sup4.cml
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617002984/fm30482sup6.hkl
Contains datablock 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617002984/fm30483sup7.hkl
Contains datablock 3

CCDC references: 1546011; 1546012; 1546013

Computing details top

For all compounds, data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) and PLATON (Spek, 2009).

(1) (S)-2-[1-(3-Ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-4-acetamidoisoindoline-1,3-dione ethyl acetate hemisolvate top
Crystal data top
C22H24N2O7S·0.5C4H8O2Dx = 1.327 Mg m3
Mr = 504.54Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P41212Cell parameters from 25 reflections
a = 13.0307 (18) Åθ = 9–12°
c = 29.754 (6) ŵ = 0.18 mm1
V = 5052.2 (17) Å3T = 293 K
Z = 8Block, colourless
F(000) = 21280.3 × 0.2 × 0.1 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
θmax = 25.4°, θmin = 1.7°
ω/2θ scansh = 1515
7571 measured reflectionsk = 150
4617 independent reflectionsl = 350
2777 reflections with I > 2σ(I)1 standard reflections every 60 reflections
Rint = 0.061 intensity decay: 1%
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.058 w = 1/[σ2(Fo2) + (0.067P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.143(Δ/σ)max = 0.001
S = 0.96Δρmax = 0.17 e Å3
4617 reflectionsΔρmin = 0.22 e Å3
345 parametersAbsolute structure: Flack x determined using 807 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
32 restraintsAbsolute structure parameter: 0.03 (10)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.84057 (12)0.60020 (12)0.53731 (5)0.0522 (4)
O10.9254 (3)0.5579 (3)0.56191 (16)0.0721 (13)
O20.7935 (3)0.6922 (3)0.55414 (14)0.0679 (12)
O30.4666 (3)0.2486 (3)0.48318 (14)0.0641 (12)
O40.4491 (3)0.1140 (3)0.54722 (15)0.0705 (13)
O50.5361 (3)0.6031 (3)0.55366 (13)0.0593 (11)
O60.7587 (3)0.5242 (3)0.66688 (13)0.0544 (10)
O70.6748 (4)0.8016 (3)0.78838 (15)0.0742 (13)
N10.6583 (3)0.5423 (3)0.60341 (14)0.0415 (10)
N20.7012 (4)0.6828 (4)0.73425 (15)0.0529 (13)
H20.73860.63050.72760.063*
C10.7060 (4)0.4613 (4)0.57588 (18)0.0423 (13)
H10.76580.43600.59250.051*
C20.7453 (4)0.5045 (4)0.53158 (18)0.0433 (12)
H2A0.68780.53310.51510.052*
H2B0.77320.44860.51380.052*
C30.8786 (6)0.6213 (6)0.4821 (2)0.077 (2)
H3A0.92830.67560.48130.116*
H3B0.82000.64020.46440.116*
H3C0.90840.55970.47020.116*
C40.6348 (4)0.3698 (4)0.56847 (18)0.0427 (13)
C50.6225 (4)0.3000 (4)0.6021 (2)0.0522 (15)
H50.65560.31030.62940.063*
C60.5610 (5)0.2130 (4)0.5963 (2)0.0551 (16)
H60.55450.16550.61940.066*
C70.5103 (5)0.1976 (4)0.5565 (2)0.0517 (15)
C80.5205 (4)0.2690 (4)0.5218 (2)0.0510 (14)
C90.5818 (4)0.3541 (4)0.5282 (2)0.0515 (15)
H90.58790.40210.50520.062*
C100.4688 (5)0.3237 (5)0.4481 (2)0.0682 (19)
H10A0.53830.33170.43710.082*
H10B0.44570.38940.45960.082*
C110.4004 (7)0.2898 (6)0.4110 (3)0.105 (3)
H11A0.40350.33870.38680.158*
H11B0.33110.28500.42180.158*
H11C0.42240.22390.40030.158*
C120.4314 (7)0.0455 (5)0.5843 (3)0.094 (3)
H12A0.38920.01070.57460.141*
H12B0.39720.08180.60800.141*
H12C0.49580.01960.59510.141*
C130.5795 (4)0.6082 (4)0.5895 (2)0.0465 (14)
C140.5633 (4)0.6827 (4)0.62655 (19)0.0458 (13)
C150.4952 (5)0.7644 (4)0.6297 (2)0.0596 (16)
H150.45000.78100.60660.072*
C160.4988 (5)0.8195 (5)0.6693 (2)0.0572 (16)
H160.45440.87480.67260.069*
C170.5642 (4)0.7971 (4)0.7039 (2)0.0545 (15)
H170.56310.83690.72980.065*
C180.6331 (4)0.7144 (4)0.70054 (19)0.0447 (13)
C190.6307 (4)0.6579 (4)0.66090 (18)0.0413 (13)
C200.6915 (4)0.5690 (4)0.64645 (18)0.0413 (12)
C210.7160 (5)0.7227 (5)0.7755 (2)0.0548 (15)
C220.7870 (6)0.6629 (6)0.8051 (2)0.077 (2)
H22A0.80150.70180.83180.115*
H22B0.84980.64940.78930.115*
H22C0.75520.59910.81330.115*
O150.5512 (8)0.4488 (8)0.25000.157 (4)
C450.433 (4)0.593 (5)0.245 (3)0.199 (14)0.5
H45A0.48900.62920.23200.298*0.5
H45B0.39810.63680.26630.298*0.5
H45C0.38550.57210.22220.298*0.5
O160.464 (3)0.462 (3)0.3131 (11)0.314 (15)0.5
C460.473 (3)0.497 (3)0.2700 (13)0.187 (10)0.5
C470.596 (2)0.371 (2)0.2723 (10)0.172 (9)0.5
H47A0.54790.31450.27690.207*0.5
H47B0.62250.39290.30110.207*0.5
C480.683 (5)0.340 (5)0.239 (2)0.247 (16)0.5
H48A0.70570.27170.24590.371*0.5
H48B0.73980.38680.24290.371*0.5
H48C0.65840.34340.20900.371*0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0539 (9)0.0522 (9)0.0503 (9)0.0110 (7)0.0039 (8)0.0052 (8)
O10.054 (2)0.075 (3)0.087 (3)0.008 (2)0.021 (2)0.001 (3)
O20.083 (3)0.052 (2)0.069 (3)0.003 (2)0.008 (2)0.011 (2)
O30.081 (3)0.055 (2)0.056 (3)0.021 (2)0.023 (2)0.008 (2)
O40.080 (3)0.051 (2)0.080 (3)0.022 (2)0.001 (2)0.008 (2)
O50.059 (2)0.073 (3)0.046 (2)0.001 (2)0.015 (2)0.007 (2)
O60.062 (3)0.056 (3)0.046 (2)0.0124 (19)0.013 (2)0.0011 (19)
O70.094 (3)0.071 (3)0.058 (3)0.010 (3)0.003 (2)0.020 (2)
N10.042 (2)0.045 (2)0.039 (3)0.003 (2)0.006 (2)0.001 (2)
N20.064 (3)0.053 (3)0.042 (3)0.012 (3)0.009 (2)0.007 (2)
C10.043 (3)0.051 (3)0.033 (3)0.002 (3)0.003 (3)0.002 (3)
C20.045 (3)0.047 (3)0.037 (3)0.005 (2)0.000 (3)0.005 (3)
C30.089 (5)0.087 (5)0.055 (4)0.020 (4)0.020 (4)0.006 (4)
C40.046 (3)0.047 (3)0.036 (3)0.001 (3)0.002 (3)0.003 (3)
C50.062 (4)0.054 (4)0.041 (3)0.001 (3)0.001 (3)0.007 (3)
C60.068 (4)0.044 (3)0.053 (4)0.008 (3)0.004 (3)0.012 (3)
C70.060 (4)0.042 (3)0.054 (4)0.008 (3)0.004 (3)0.005 (3)
C80.056 (4)0.044 (3)0.054 (4)0.004 (3)0.005 (3)0.002 (3)
C90.056 (4)0.041 (3)0.058 (4)0.005 (3)0.000 (3)0.009 (3)
C100.086 (5)0.054 (4)0.064 (4)0.006 (4)0.020 (4)0.002 (3)
C110.141 (8)0.096 (6)0.080 (6)0.020 (6)0.048 (6)0.010 (5)
C120.140 (7)0.061 (4)0.080 (6)0.040 (5)0.023 (5)0.006 (4)
C130.046 (3)0.051 (3)0.043 (3)0.004 (3)0.007 (3)0.010 (3)
C140.042 (3)0.048 (3)0.048 (3)0.001 (3)0.007 (3)0.006 (3)
C150.048 (3)0.060 (4)0.070 (4)0.009 (3)0.010 (3)0.007 (4)
C160.052 (3)0.049 (4)0.071 (5)0.016 (3)0.007 (3)0.005 (3)
C170.052 (3)0.049 (3)0.063 (4)0.002 (3)0.003 (3)0.004 (3)
C180.044 (3)0.043 (3)0.047 (4)0.003 (2)0.004 (3)0.003 (3)
C190.043 (3)0.042 (3)0.040 (3)0.004 (2)0.000 (3)0.007 (3)
C200.044 (3)0.044 (3)0.036 (3)0.005 (3)0.006 (3)0.007 (3)
C210.056 (4)0.066 (4)0.042 (4)0.002 (3)0.001 (3)0.005 (3)
C220.090 (5)0.079 (5)0.061 (4)0.005 (4)0.019 (4)0.002 (4)
O150.129 (5)0.129 (5)0.213 (12)0.008 (7)0.052 (6)0.052 (6)
C450.12 (3)0.17 (3)0.31 (3)0.01 (2)0.05 (2)0.060 (18)
O160.29 (3)0.36 (4)0.29 (2)0.04 (3)0.001 (18)0.01 (2)
C460.139 (14)0.155 (19)0.27 (2)0.004 (12)0.041 (15)0.074 (16)
C470.143 (19)0.118 (13)0.26 (2)0.016 (12)0.084 (15)0.086 (13)
C480.17 (2)0.24 (5)0.33 (5)0.03 (3)0.06 (3)0.15 (3)
Geometric parameters (Å, º) top
S1—O11.436 (5)C10—C111.487 (9)
S1—O21.437 (4)C11—H11A0.9600
S1—C21.768 (5)C11—H11B0.9600
S1—C31.737 (6)C11—H11C0.9600
O3—C81.373 (7)C12—H12A0.9600
O3—C101.431 (7)C12—H12B0.9600
O4—C71.379 (7)C12—H12C0.9600
O4—C121.438 (7)C13—C141.484 (8)
O5—C131.208 (6)C14—C151.390 (8)
O6—C201.216 (6)C14—C191.386 (7)
O7—C211.222 (7)C15—H150.9300
N1—C11.474 (6)C15—C161.380 (9)
N1—C131.402 (7)C16—H160.9300
N1—C201.396 (7)C16—C171.369 (8)
N2—H20.8597C17—H170.9300
N2—C181.401 (7)C17—C181.406 (7)
N2—C211.346 (7)C18—C191.391 (7)
C1—H10.9800C19—C201.468 (7)
C1—C21.522 (7)C21—C221.496 (8)
C1—C41.526 (7)C22—H22A0.9600
C2—H2A0.9700C22—H22B0.9600
C2—H2B0.9700C22—H22C0.9600
C3—H3A0.9600O15—C461.34 (3)
C3—H3B0.9600O15—C471.34 (2)
C3—H3C0.9600C45—H45A0.9600
C4—C51.361 (7)C45—H45B0.9600
C4—C91.399 (8)C45—H45C0.9600
C5—H50.9300C45—C461.54 (2)
C5—C61.399 (8)O16—C461.37 (4)
C6—H60.9300C47—H47A0.9700
C6—C71.369 (8)C47—H47B0.9700
C7—C81.398 (8)C47—C481.56 (2)
C8—C91.379 (7)C48—H48A0.9600
C9—H90.9300C48—H48B0.9600
C10—H10A0.9700C48—H48C0.9600
C10—H10B0.9700
O1—S1—O2118.1 (3)O4—C12—H12A109.5
O1—S1—C2108.6 (3)O4—C12—H12B109.5
O1—S1—C3108.8 (3)O4—C12—H12C109.5
O2—S1—C2108.8 (3)H12A—C12—H12B109.5
O2—S1—C3108.6 (3)H12A—C12—H12C109.5
C3—S1—C2102.8 (3)H12B—C12—H12C109.5
C8—O3—C10117.8 (4)O5—C13—N1124.7 (5)
C7—O4—C12115.4 (5)O5—C13—C14128.7 (5)
C13—N1—C1125.7 (4)N1—C13—C14106.6 (5)
C20—N1—C1123.9 (4)C15—C14—C13129.9 (5)
C20—N1—C13110.2 (4)C19—C14—C13107.8 (5)
C18—N2—H2115.3C19—C14—C15122.3 (6)
C21—N2—H2115.6C14—C15—H15122.1
C21—N2—C18129.0 (5)C16—C15—C14115.7 (6)
N1—C1—H1107.1C16—C15—H15122.1
N1—C1—C2111.0 (4)C15—C16—H16118.2
N1—C1—C4112.5 (4)C17—C16—C15123.6 (5)
C2—C1—H1107.1C17—C16—H16118.2
C2—C1—C4111.6 (4)C16—C17—H17119.7
C4—C1—H1107.1C16—C17—C18120.5 (6)
S1—C2—H2A108.6C18—C17—H17119.7
S1—C2—H2B108.6N2—C18—C17125.3 (5)
C1—C2—S1114.4 (4)C19—C18—N2117.8 (5)
C1—C2—H2A108.6C19—C18—C17116.9 (5)
C1—C2—H2B108.6C14—C19—C18121.1 (5)
H2A—C2—H2B107.6C14—C19—C20108.1 (5)
S1—C3—H3A109.5C18—C19—C20130.9 (5)
S1—C3—H3B109.5O6—C20—N1124.2 (5)
S1—C3—H3C109.5O6—C20—C19128.4 (5)
H3A—C3—H3B109.5N1—C20—C19107.4 (4)
H3A—C3—H3C109.5O7—C21—N2123.2 (6)
H3B—C3—H3C109.5O7—C21—C22121.7 (6)
C5—C4—C1119.2 (5)N2—C21—C22115.1 (6)
C5—C4—C9118.3 (5)C21—C22—H22A109.5
C9—C4—C1122.6 (5)C21—C22—H22B109.5
C4—C5—H5119.4C21—C22—H22C109.5
C4—C5—C6121.2 (5)H22A—C22—H22B109.5
C6—C5—H5119.4H22A—C22—H22C109.5
C5—C6—H6119.9H22B—C22—H22C109.5
C7—C6—C5120.1 (5)C46—O15—C47118 (2)
C7—C6—H6119.9H45A—C45—H45B109.5
O4—C7—C8115.6 (5)H45A—C45—H45C109.5
C6—C7—O4124.6 (5)H45B—C45—H45C109.5
C6—C7—C8119.7 (5)C46—C45—H45A109.5
O3—C8—C7116.2 (5)C46—C45—H45B109.5
O3—C8—C9124.6 (5)C46—C45—H45C109.5
C9—C8—C7119.3 (6)O15—C46—C45116 (3)
C4—C9—H9119.3O15—C46—O16109 (3)
C8—C9—C4121.4 (5)O16—C46—C45133 (4)
C8—C9—H9119.3O15—C47—H47A111.5
O3—C10—H10A109.9O15—C47—H47B111.5
O3—C10—H10B109.9O15—C47—C48101 (2)
O3—C10—C11109.1 (5)H47A—C47—H47B109.3
H10A—C10—H10B108.3C48—C47—H47A111.5
C11—C10—H10A109.9C48—C47—H47B111.5
C11—C10—H10B109.9C47—C48—H48A109.5
C10—C11—H11A109.5C47—C48—H48B109.5
C10—C11—H11B109.5C47—C48—H48C109.5
C10—C11—H11C109.5H48A—C48—H48B109.5
H11A—C11—H11B109.5H48A—C48—H48C109.5
H11A—C11—H11C109.5H48B—C48—H48C109.5
H11B—C11—H11C109.5
O1—S1—C2—C158.1 (5)C10—O3—C8—C94.0 (8)
O2—S1—C2—C171.7 (5)C12—O4—C7—C66.5 (9)
O3—C8—C9—C4179.9 (5)C12—O4—C7—C8174.7 (6)
O4—C7—C8—O31.6 (8)C13—N1—C1—C254.0 (6)
O4—C7—C8—C9179.0 (5)C13—N1—C1—C471.9 (6)
O5—C13—C14—C150.1 (10)C13—N1—C20—O6179.6 (5)
O5—C13—C14—C19179.8 (6)C13—N1—C20—C190.4 (6)
N1—C1—C2—S161.0 (5)C13—C14—C15—C16179.8 (6)
N1—C1—C4—C578.2 (6)C13—C14—C19—C18179.7 (5)
N1—C1—C4—C9102.4 (6)C13—C14—C19—C200.6 (6)
N1—C13—C14—C15179.3 (6)C14—C15—C16—C170.0 (9)
N1—C13—C14—C190.8 (6)C14—C19—C20—O6179.9 (5)
N2—C18—C19—C14178.1 (5)C14—C19—C20—N10.2 (6)
N2—C18—C19—C202.3 (9)C15—C14—C19—C180.1 (8)
C1—N1—C13—O54.6 (8)C15—C14—C19—C20179.5 (5)
C1—N1—C13—C14174.8 (5)C15—C16—C17—C180.1 (10)
C1—N1—C20—O64.8 (8)C16—C17—C18—N2178.1 (6)
C1—N1—C20—C19175.2 (4)C16—C17—C18—C190.1 (8)
C1—C4—C5—C6177.7 (5)C17—C18—C19—C140.0 (8)
C1—C4—C9—C8177.8 (5)C17—C18—C19—C20179.5 (5)
C2—C1—C4—C5156.3 (5)C18—N2—C21—O76.1 (10)
C2—C1—C4—C923.2 (7)C18—N2—C21—C22173.5 (6)
C3—S1—C2—C1173.3 (4)C18—C19—C20—O60.3 (10)
C4—C1—C2—S1172.6 (4)C18—C19—C20—N1179.8 (5)
C4—C5—C6—C71.2 (9)C19—C14—C15—C160.1 (9)
C5—C4—C9—C81.7 (8)C20—N1—C1—C2120.9 (5)
C5—C6—C7—O4179.0 (5)C20—N1—C1—C4113.2 (5)
C5—C6—C7—C80.2 (9)C20—N1—C13—O5179.8 (5)
C6—C7—C8—O3179.4 (5)C20—N1—C13—C140.7 (6)
C6—C7—C8—C90.1 (9)C21—N2—C18—C170.4 (9)
C7—C8—C9—C40.8 (8)C21—N2—C18—C19178.4 (6)
C8—O3—C10—C11176.3 (6)C46—O15—C47—C48177 (4)
C9—C4—C5—C61.9 (8)C47—O15—C46—C45174 (5)
C10—O3—C8—C7175.3 (5)C47—O15—C46—O167 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O60.862.292.974 (6)136
C2—H2A···O5i0.972.333.171 (7)145
C2—H2A···O50.972.463.087 (7)122
C2—H2B···O7ii0.972.563.524 (7)173
C3—H3A···O6iii0.962.443.132 (7)129
C3—H3B···O2i0.962.653.476 (9)145
C6—H6···O1ii0.932.493.403 (8)167
C9—H9···O5i0.932.483.408 (7)177
C12—H12A···O7iv0.962.653.595 (9)169
C17—H17···O70.932.312.896 (8)120
Symmetry codes: (i) y, x, z+1; (ii) x+3/2, y1/2, z+5/4; (iii) y+1/2, x+3/2, z1/4; (iv) y1/2, x+1/2, z1/4.
(2) (S)-2-[1-(3-Ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-4-acetamidoisoindoline-1,3-dione toluene hemisolvate top
Crystal data top
C22H24N2O7S·0.5C7H8Dx = 1.343 Mg m3
Mr = 506.56Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P41212Cell parameters from 25 reflections
a = 12.980 (3) Åθ = 9–12°
c = 29.734 (6) ŵ = 0.18 mm1
V = 5010 (3) Å3T = 293 K
Z = 8Block, colourless
F(000) = 21360.2 × 0.1 × 0.1 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
θmax = 25.0°, θmin = 1.7°
ω/2θ scansh = 1515
7337 measured reflectionsk = 150
4433 independent reflectionsl = 350
1916 reflections with I > 2σ(I)1 standard reflections every 60 reflections
Rint = 0.099 intensity decay: 1%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.099 w = 1/[σ2(Fo2) + (0.0625P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.224(Δ/σ)max < 0.001
S = 1.01Δρmax = 0.27 e Å3
4433 reflectionsΔρmin = 0.26 e Å3
321 parametersAbsolute structure: Flack x determined using 403 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
87 restraintsAbsolute structure parameter: 0.1 (2)
Primary atom site location: dual
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2. Uiso/Uaniso restraints and constraints Uanis(C48) ~Ueq, Uanis(C45) ~Ueq, Uanis(C46) ~Ueq, Uanis(C50) ~Ueq, Uanis(C47) ~Ueq, Uanis(C49) ~Ueq, Uanis(C51) ~Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 3. Rigid body (RIGU) restrains C45, C46, C47, C48, C49, C50, C51 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 4. Others Fixed Sof: C45(0.5) H45(0.5) C46(0.5) H46(0.5) C47(0.5) H47(0.5) C48(0.5) H48(0.5) C49(0.5) H49(0.5) C50(0.5) C51(0.5) H51A(0.5) H51B(0.5) H51C(0.5) 5.a Ternary CH refined with riding coordinates: C1(H1) 5.b Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C10(H10A,H10B) 5.c Aromatic/amide H refined with riding coordinates: N2(H2), C5(H5), C8(H8), C9(H9), C15(H15), C16(H16), C17(H17), C45(H45), C46(H46), C47(H47), C48(H48), C49(H49) 5.d Fitted hexagon refined as free rotating group: C4(C5,C6,C7,C8,C9), C14(C15,C16,C17,C18,C19), C45(C46,C47,C48,C49,C50) 5.e Idealised Me refined as rotating group: C3(H3A,H3B,H3C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C22(H22A,H22B, H22C), C51(H51A,H51B,H51C)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.1605 (2)0.5996 (2)0.71358 (10)0.0541 (7)
O10.2073 (5)0.6918 (5)0.6956 (2)0.069 (2)
O20.0732 (5)0.5572 (5)0.6882 (3)0.070 (2)
O30.5370 (5)0.2469 (5)0.7659 (2)0.069 (2)
O40.5544 (5)0.1111 (5)0.7012 (3)0.077 (2)
O50.4666 (5)0.6011 (6)0.6956 (2)0.063 (2)
O60.2364 (5)0.5239 (5)0.5839 (2)0.056 (2)
O70.3242 (5)0.7975 (5)0.4604 (3)0.072 (2)
N10.3419 (5)0.5391 (6)0.6464 (3)0.041 (2)
N20.2963 (6)0.6819 (6)0.5156 (3)0.054 (2)
H20.25900.62930.52230.065*
C10.2935 (7)0.4604 (7)0.6750 (4)0.054 (3)
H10.23280.43470.65890.064*
C20.2560 (7)0.5033 (7)0.7203 (3)0.053 (3)
H2A0.31420.53210.73650.063*
H2B0.22820.44740.73820.063*
C30.1219 (9)0.6235 (8)0.7696 (4)0.085 (4)
H3A0.18160.63690.78770.128*
H3B0.08620.56440.78110.128*
H3C0.07700.68230.77030.128*
C40.3668 (3)0.3676 (3)0.68242 (18)0.042 (2)
C50.4197 (4)0.3525 (4)0.72254 (17)0.049 (3)
H50.41290.39990.74580.058*
C60.4827 (5)0.2668 (4)0.72783 (19)0.052 (3)
C70.4929 (4)0.1961 (3)0.6930 (2)0.051 (3)
C80.4400 (5)0.2111 (4)0.6529 (2)0.058 (3)
H80.44680.16380.62960.070*
C90.3770 (4)0.2968 (4)0.64759 (16)0.055 (3)
H90.34160.30690.62080.066*
C100.5370 (8)0.3212 (8)0.8012 (4)0.073 (4)
H10A0.46880.32540.81450.087*
H10B0.55440.38840.78920.087*
C110.6137 (10)0.2914 (9)0.8365 (4)0.104 (5)
H11A0.67970.28060.82280.155*
H11B0.59160.22910.85100.155*
H11C0.61880.34550.85840.155*
C120.5718 (11)0.0421 (9)0.6639 (4)0.106 (5)
H12A0.60460.07890.63980.160*
H12B0.50710.01510.65360.160*
H12C0.61530.01360.67340.160*
C130.4202 (7)0.6045 (8)0.6600 (4)0.055 (3)
C140.4363 (4)0.6793 (4)0.62356 (17)0.049 (3)
C150.5047 (4)0.7609 (4)0.6183 (2)0.064 (3)
H150.55100.77680.64110.077*
C160.5038 (4)0.8185 (4)0.5789 (2)0.068 (4)
H160.54950.87310.57530.082*
C170.4346 (5)0.7946 (5)0.54477 (19)0.060 (3)
H170.43400.83320.51840.071*
C180.3662 (4)0.7131 (5)0.55005 (18)0.049 (3)
C190.3671 (4)0.6554 (4)0.58945 (19)0.044 (3)
C200.3052 (7)0.5686 (7)0.6042 (3)0.043 (2)
C210.2791 (7)0.7213 (8)0.4743 (4)0.059 (3)
C220.2084 (8)0.6592 (8)0.4454 (4)0.074 (4)
H22A0.19020.69830.41920.110*
H22B0.14720.64250.46200.110*
H22C0.24240.59680.43640.110*
C450.5776 (13)0.5377 (13)0.5355 (7)0.091 (5)0.5
H450.62620.56190.55600.110*0.5
C460.5124 (16)0.4572 (14)0.5474 (7)0.097 (6)0.5
H460.51730.42760.57580.117*0.5
C470.440 (2)0.421 (2)0.5168 (8)0.089 (6)0.5
H470.39620.36730.52480.107*0.5
C480.4325 (19)0.465 (2)0.4744 (8)0.103 (6)0.5
H480.38400.44130.45400.124*0.5
C490.4978 (17)0.5459 (17)0.4625 (7)0.110 (6)0.5
H490.49290.57560.43420.132*0.5
C500.5703 (15)0.5820 (14)0.4931 (8)0.096 (5)0.5
C510.630 (2)0.669 (2)0.4782 (10)0.148 (9)0.5
H51A0.63070.72070.50110.222*0.5
H51B0.60060.69640.45120.222*0.5
H51C0.69970.64690.47220.222*0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0502 (15)0.0470 (14)0.0652 (17)0.0127 (13)0.0022 (15)0.0027 (15)
O10.080 (5)0.052 (4)0.075 (6)0.003 (4)0.012 (4)0.020 (4)
O20.040 (4)0.075 (5)0.096 (6)0.002 (4)0.010 (4)0.015 (4)
O30.076 (5)0.055 (4)0.075 (5)0.009 (4)0.025 (4)0.008 (4)
O40.074 (5)0.056 (4)0.100 (7)0.018 (4)0.008 (5)0.008 (5)
O50.049 (4)0.076 (5)0.065 (5)0.012 (4)0.000 (4)0.015 (4)
O60.054 (4)0.052 (4)0.062 (5)0.008 (3)0.014 (4)0.001 (4)
O70.069 (5)0.074 (5)0.071 (5)0.011 (4)0.008 (4)0.024 (4)
N10.030 (4)0.039 (4)0.054 (5)0.003 (3)0.006 (4)0.005 (4)
N20.045 (5)0.059 (5)0.058 (6)0.007 (4)0.011 (4)0.007 (4)
C10.045 (6)0.047 (6)0.069 (7)0.010 (5)0.008 (6)0.002 (6)
C20.052 (6)0.034 (5)0.072 (7)0.013 (4)0.004 (6)0.009 (5)
C30.122 (10)0.068 (8)0.065 (8)0.032 (7)0.026 (7)0.006 (6)
C40.043 (6)0.028 (5)0.056 (6)0.005 (4)0.002 (5)0.005 (4)
C50.046 (6)0.035 (5)0.065 (7)0.000 (4)0.000 (5)0.009 (5)
C60.060 (7)0.042 (6)0.054 (7)0.004 (5)0.006 (5)0.005 (5)
C70.065 (6)0.023 (5)0.065 (7)0.011 (5)0.013 (6)0.001 (5)
C80.051 (6)0.047 (6)0.076 (8)0.001 (5)0.017 (6)0.014 (6)
C90.060 (7)0.027 (5)0.077 (8)0.007 (5)0.007 (6)0.002 (5)
C100.084 (8)0.068 (7)0.067 (8)0.005 (7)0.028 (7)0.015 (7)
C110.139 (12)0.077 (9)0.094 (10)0.012 (9)0.047 (9)0.021 (8)
C120.152 (12)0.068 (8)0.099 (11)0.058 (8)0.032 (9)0.027 (7)
C130.037 (6)0.055 (6)0.072 (8)0.003 (5)0.008 (5)0.016 (6)
C140.050 (6)0.038 (6)0.058 (7)0.001 (5)0.005 (5)0.002 (5)
C150.047 (6)0.051 (6)0.094 (9)0.007 (6)0.003 (6)0.002 (6)
C160.040 (6)0.059 (7)0.105 (10)0.011 (6)0.005 (6)0.000 (7)
C170.046 (6)0.046 (6)0.087 (9)0.010 (5)0.011 (6)0.019 (6)
C180.036 (5)0.049 (6)0.062 (7)0.005 (5)0.007 (5)0.014 (5)
C190.038 (5)0.031 (5)0.064 (7)0.005 (4)0.013 (5)0.002 (5)
C200.045 (5)0.039 (5)0.046 (6)0.012 (5)0.005 (5)0.005 (5)
C210.038 (6)0.064 (7)0.074 (8)0.001 (5)0.007 (6)0.000 (6)
C220.067 (7)0.068 (7)0.086 (9)0.004 (6)0.011 (7)0.003 (7)
C450.081 (9)0.083 (8)0.110 (8)0.015 (7)0.021 (6)0.017 (6)
C460.089 (9)0.094 (9)0.109 (9)0.007 (7)0.009 (7)0.010 (7)
C470.080 (9)0.087 (9)0.100 (8)0.017 (7)0.012 (6)0.016 (6)
C480.102 (10)0.101 (9)0.107 (8)0.015 (7)0.011 (7)0.010 (7)
C490.109 (9)0.104 (9)0.118 (9)0.013 (7)0.016 (7)0.012 (7)
C500.093 (8)0.090 (8)0.104 (8)0.020 (6)0.023 (6)0.018 (6)
C510.158 (15)0.125 (12)0.161 (17)0.012 (10)0.034 (12)0.002 (10)
Geometric parameters (Å, º) top
S1—O11.445 (7)C11—H11A0.9600
S1—O21.468 (7)C11—H11B0.9600
S1—C21.772 (9)C11—H11C0.9600
S1—C31.766 (11)C12—H12A0.9600
O3—C61.359 (8)C12—H12B0.9600
O3—C101.425 (11)C12—H12C0.9600
O4—C71.384 (8)C13—C141.470 (12)
O4—C121.443 (12)C14—C151.3900
O5—C131.219 (11)C14—C191.3900
O6—C201.225 (10)C15—H150.9300
O7—C211.222 (11)C15—C161.3900
N1—C11.469 (12)C16—H160.9300
N1—C131.386 (11)C16—C171.3900
N1—C201.395 (11)C17—H170.9300
N2—H20.8600C17—C181.3900
N2—C181.427 (9)C18—C191.3900
N2—C211.348 (12)C19—C201.451 (10)
C1—H10.9800C21—C221.494 (13)
C1—C21.539 (13)C22—H22A0.9600
C1—C41.552 (10)C22—H22B0.9600
C2—H2A0.9700C22—H22C0.9600
C2—H2B0.9700C45—H450.9300
C3—H3A0.9600C45—C461.3900
C3—H3B0.9600C45—C501.3900
C3—H3C0.9600C46—H460.9300
C4—C51.3900C46—C471.3900
C4—C91.3900C47—H470.9300
C5—H50.9300C47—C481.3900
C5—C61.3900C48—H480.9300
C6—C71.3900C48—C491.3900
C7—C81.3900C49—H490.9300
C8—H80.9300C49—C501.3900
C8—C91.3900C50—C511.44 (3)
C9—H90.9300C51—H51A0.9600
C10—H10A0.9700C51—H51B0.9600
C10—H10B0.9700C51—H51C0.9600
C10—C111.497 (14)
O1—S1—O2116.4 (4)O4—C12—H12B109.5
O1—S1—C2109.4 (4)O4—C12—H12C109.5
O1—S1—C3108.8 (5)H12A—C12—H12B109.5
O2—S1—C2109.6 (4)H12A—C12—H12C109.5
O2—S1—C3109.4 (5)H12B—C12—H12C109.5
C3—S1—C2102.4 (5)O5—C13—N1126.5 (10)
C6—O3—C10119.1 (7)O5—C13—C14126.5 (9)
C7—O4—C12116.8 (8)N1—C13—C14107.1 (8)
C13—N1—C1124.7 (8)C15—C14—C13132.6 (5)
C13—N1—C20110.2 (8)C15—C14—C19120.0
C20—N1—C1124.4 (7)C19—C14—C13107.4 (5)
C18—N2—H2114.7C14—C15—H15120.0
C21—N2—H2114.7C16—C15—C14120.0
C21—N2—C18130.6 (8)C16—C15—H15120.0
N1—C1—H1107.3C15—C16—H16120.0
N1—C1—C2113.1 (8)C15—C16—C17120.0
N1—C1—C4111.1 (7)C17—C16—H16120.0
C2—C1—H1107.3C16—C17—H17120.0
C2—C1—C4110.4 (7)C18—C17—C16120.0
C4—C1—H1107.3C18—C17—H17120.0
S1—C2—H2A109.2C17—C18—N2122.7 (5)
S1—C2—H2B109.2C19—C18—N2117.2 (5)
C1—C2—S1112.1 (7)C19—C18—C17120.0
C1—C2—H2A109.2C14—C19—C20108.1 (5)
C1—C2—H2B109.2C18—C19—C14120.0
H2A—C2—H2B107.9C18—C19—C20131.9 (5)
S1—C3—H3A109.5O6—C20—N1124.2 (8)
S1—C3—H3B109.5O6—C20—C19128.5 (8)
S1—C3—H3C109.5N1—C20—C19107.2 (7)
H3A—C3—H3B109.5O7—C21—N2122.4 (10)
H3A—C3—H3C109.5O7—C21—C22122.4 (10)
H3B—C3—H3C109.5N2—C21—C22114.9 (9)
C5—C4—C1122.3 (5)C21—C22—H22A109.5
C5—C4—C9120.0C21—C22—H22B109.5
C9—C4—C1117.7 (5)C21—C22—H22C109.5
C4—C5—H5120.0H22A—C22—H22B109.5
C6—C5—C4120.0H22A—C22—H22C109.5
C6—C5—H5120.0H22B—C22—H22C109.5
O3—C6—C5123.5 (5)C46—C45—H45120.0
O3—C6—C7116.5 (5)C46—C45—C50120.0
C5—C6—C7120.0C50—C45—H45120.0
O4—C7—C6116.8 (5)C45—C46—H46120.0
O4—C7—C8123.2 (5)C47—C46—C45120.0
C8—C7—C6120.0C47—C46—H46120.0
C7—C8—H8120.0C46—C47—H47120.0
C7—C8—C9120.0C48—C47—C46120.0
C9—C8—H8120.0C48—C47—H47120.0
C4—C9—H9120.0C47—C48—H48120.0
C8—C9—C4120.0C47—C48—C49120.0
C8—C9—H9120.0C49—C48—H48120.0
O3—C10—H10A109.7C48—C49—H49120.0
O3—C10—H10B109.7C48—C49—C50120.0
O3—C10—C11110.0 (9)C50—C49—H49120.0
H10A—C10—H10B108.2C45—C50—C51124.5 (17)
C11—C10—H10A109.7C49—C50—C45120.0
C11—C10—H10B109.7C49—C50—C51115.4 (17)
C10—C11—H11A109.5C50—C51—H51A109.5
C10—C11—H11B109.5C50—C51—H51B109.5
C10—C11—H11C109.5C50—C51—H51C109.5
H11A—C11—H11B109.5H51A—C51—H51B109.5
H11A—C11—H11C109.5H51A—C51—H51C109.5
H11B—C11—H11C109.5H51B—C51—H51C109.5
O4—C12—H12A109.5
O1—S1—C2—C171.1 (8)C13—N1—C1—C251.6 (12)
O2—S1—C2—C157.6 (8)C13—N1—C1—C473.3 (11)
O3—C6—C7—O42.1 (6)C13—N1—C20—O6179.5 (9)
O3—C6—C7—C8179.9 (6)C13—N1—C20—C192.5 (10)
O4—C7—C8—C9177.9 (6)C13—C14—C15—C16178.6 (7)
O5—C13—C14—C151.5 (14)C13—C14—C19—C18178.9 (5)
O5—C13—C14—C19179.7 (9)C13—C14—C19—C201.7 (6)
N1—C1—C2—S161.7 (9)C14—C15—C16—C170.0
N1—C1—C4—C5104.0 (7)C14—C19—C20—O6179.4 (8)
N1—C1—C4—C977.4 (8)C14—C19—C20—N12.6 (7)
N1—C13—C14—C15178.9 (5)C15—C14—C19—C180.0
N1—C13—C14—C190.2 (8)C15—C14—C19—C20179.4 (5)
N2—C18—C19—C14177.4 (6)C15—C16—C17—C180.0
N2—C18—C19—C203.3 (7)C16—C17—C18—N2177.3 (6)
C1—N1—C13—O57.0 (16)C16—C17—C18—C190.0
C1—N1—C13—C14172.6 (7)C17—C18—C19—C140.0
C1—N1—C20—O69.3 (14)C17—C18—C19—C20179.2 (7)
C1—N1—C20—C19173.6 (7)C18—N2—C21—O71.8 (16)
C1—C4—C5—C6178.6 (5)C18—N2—C21—C22172.6 (8)
C1—C4—C9—C8178.7 (5)C18—C19—C20—O61.2 (13)
C2—C1—C4—C522.3 (9)C18—C19—C20—N1178.1 (5)
C2—C1—C4—C9156.3 (6)C19—C14—C15—C160.0
C3—S1—C2—C1173.6 (7)C20—N1—C1—C2118.3 (9)
C4—C1—C2—S1173.1 (5)C20—N1—C1—C4116.9 (9)
C4—C5—C6—O3179.9 (7)C20—N1—C13—O5178.1 (10)
C4—C5—C6—C70.0C20—N1—C13—C141.5 (10)
C5—C4—C9—C80.0C21—N2—C18—C171.9 (12)
C5—C6—C7—O4178.1 (6)C21—N2—C18—C19179.2 (8)
C5—C6—C7—C80.0C45—C46—C47—C480.0
C6—O3—C10—C11171.3 (9)C46—C45—C50—C490.0
C6—C7—C8—C90.0C46—C45—C50—C51177 (3)
C7—C8—C9—C40.0C46—C47—C48—C490.0
C9—C4—C5—C60.0C47—C48—C49—C500.0
C10—O3—C6—C55.5 (10)C48—C49—C50—C450.0
C10—O3—C6—C7174.4 (7)C48—C49—C50—C51177 (2)
C12—O4—C7—C6175.0 (7)C50—C45—C46—C470.0
C12—O4—C7—C87.0 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O60.862.302.988 (10)137
C2—H2A···O5i0.972.303.135 (12)144
C2—H2A···O50.972.493.101 (12)121
C2—H2B···O7ii0.972.563.530 (12)173
C3—H3A···O1i0.962.653.427 (14)138
C3—H3C···O6iii0.962.403.063 (12)126
C5—H5···O5i0.932.463.392 (8)177
C8—H8···O2ii0.932.463.370 (9)167
C12—H12C···O7iv0.962.633.576 (13)168
C17—H17···O70.932.282.889 (9)122
Symmetry codes: (i) y+1, x+1, z+3/2; (ii) x+1/2, y1/2, z+5/4; (iii) y+1/2, x+1/2, z+1/4; (iv) y+3/2, x1/2, z+1/4.
(3) (S)-2-[1-(3-Ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-4-acetamidoisoindoline-1,3-dione dichloromethane monosolvate top
Crystal data top
C22H24N2O7S·CH2Cl2Dx = 1.415 Mg m3
Mr = 545.42Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P41212Cell parameters from 25 reflections
a = 13.171 (3) Åθ = 9–13°
c = 29.524 (6) ŵ = 0.38 mm1
V = 5122 (3) Å3T = 293 K
Z = 8Block, colourless
F(000) = 22720.3 × 0.2 × 0.1 mm
Data collection top
Nonius CAD4
diffractometer
θmax = 25.4°, θmin = 1.7°
ω/2θ scansh = 1515
7753 measured reflectionsk = 015
4697 independent reflectionsl = 035
2736 reflections with I > 2σ(I)1 standard reflections every 60 reflections
Rint = 0.051 intensity decay: 1%
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.057 w = 1/[σ2(Fo2) + (0.0529P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.135(Δ/σ)max < 0.001
S = 1.00Δρmax = 0.20 e Å3
4697 reflectionsΔρmin = 0.25 e Å3
321 parametersAbsolute structure: Flack x determined using 830 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraintsAbsolute structure parameter: 0.17 (8)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2. Others Fixed Sof: H1A(0.5) H1B(0.5) H2A(0.5) H2B(0.5) 3.a Riding coordinates: N2(H2) 3.b Ternary CH refined with riding coordinates: C4(H4) 3.c Secondary CH2 refined with riding coordinates: C3(H3A,H3B), C18(H18A,H18B), C1(H1A,H1B), C2(H2A,H2B) 3.d Aromatic/amide H refined with riding coordinates: C10(H10), C11(H11), C12(H12), C16(H16), C22(H22), C23(H23) 3.e Idealised Me refined as rotating group: C9(H9A,H9B,H9C), C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C24(H24A,H24B,H24C)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.39269 (12)0.15616 (12)0.46154 (6)0.0543 (4)
O10.4345 (3)0.0717 (3)0.43754 (16)0.0723 (13)
O20.3043 (3)0.2042 (3)0.44290 (14)0.0662 (12)
O30.4667 (3)0.2359 (3)0.33258 (14)0.0544 (11)
O40.1944 (4)0.3254 (4)0.20964 (15)0.0800 (14)
O50.3921 (3)0.4565 (3)0.44678 (14)0.0596 (12)
O60.7385 (3)0.5276 (3)0.51867 (14)0.0623 (12)
O70.8730 (3)0.5441 (3)0.45520 (15)0.0666 (13)
N10.4514 (3)0.3376 (3)0.39610 (16)0.0424 (11)
N20.3115 (4)0.2972 (4)0.26482 (16)0.0525 (13)
H20.36370.26050.27100.063*
C30.4881 (4)0.2491 (4)0.4687 (2)0.0460 (14)
H3A0.46020.30540.48580.055*
H3B0.54300.22010.48630.055*
C40.5314 (4)0.2898 (4)0.42417 (19)0.0439 (14)
H40.55720.23130.40720.053*
C50.4243 (4)0.3038 (4)0.35334 (19)0.0421 (13)
C60.3362 (4)0.3651 (4)0.3388 (2)0.0435 (14)
C70.2816 (4)0.3646 (4)0.2989 (2)0.0453 (14)
C80.2709 (5)0.2823 (5)0.2225 (2)0.0574 (16)
C90.3289 (5)0.2122 (5)0.1929 (2)0.0712 (19)
H9A0.34080.14960.20860.107*
H9B0.39270.24270.18500.107*
H9C0.29060.19890.16580.107*
C100.2003 (4)0.4329 (4)0.2954 (2)0.0557 (16)
H100.16180.43500.26910.067*
C110.1774 (5)0.4966 (5)0.3307 (3)0.0630 (18)
H110.12210.54000.32780.076*
C120.2328 (4)0.4993 (5)0.3706 (2)0.0588 (17)
H120.21730.54380.39400.071*
C130.3126 (4)0.4316 (4)0.37335 (19)0.0451 (14)
C140.3859 (5)0.4141 (4)0.4104 (2)0.0494 (15)
C150.6208 (4)0.3604 (4)0.4324 (2)0.0453 (14)
C160.6344 (4)0.4129 (4)0.4729 (2)0.0500 (15)
H160.58590.40670.49560.060*
C170.7186 (4)0.4741 (4)0.4801 (2)0.0469 (14)
C180.6667 (5)0.5196 (5)0.5547 (2)0.0628 (19)
H18A0.65900.44920.56370.075*
H18B0.60110.54490.54500.075*
C190.7052 (6)0.5811 (7)0.5937 (3)0.101 (3)
H19A0.65980.57410.61890.152*
H19B0.70900.65120.58500.152*
H19C0.77150.55750.60210.152*
C200.7910 (4)0.4842 (4)0.4452 (2)0.0503 (15)
C210.9460 (5)0.5585 (6)0.4200 (2)0.077 (2)
H21A0.99960.60170.43070.116*
H21B0.91370.58950.39430.116*
H21C0.97370.49400.41130.116*
C220.7766 (4)0.4332 (5)0.4049 (2)0.0533 (16)
H220.82410.44000.38180.064*
C230.6917 (4)0.3715 (4)0.3985 (2)0.0512 (16)
H230.68300.33760.37110.061*
C240.3660 (6)0.1209 (6)0.5174 (2)0.081 (2)
H24A0.34010.17840.53360.122*
H24B0.42700.09720.53170.122*
H24C0.31630.06760.51740.122*
Cl10.8600 (2)0.81065 (19)0.45348 (11)0.1396 (11)
C10.7849 (7)0.7849 (7)0.50000.129 (5)
H1A0.79400.71430.50840.155*0.5
H1B0.71430.79400.49160.155*0.5
Cl20.5832 (2)0.4681 (3)0.29535 (14)0.1914 (18)
C20.5070 (6)0.4930 (6)0.25000.104 (4)
H2A0.43660.48410.25890.125*0.5
H2B0.51590.56340.24110.125*0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0577 (10)0.0520 (9)0.0532 (10)0.0112 (8)0.0024 (8)0.0031 (8)
O10.080 (3)0.058 (3)0.079 (3)0.008 (2)0.002 (3)0.013 (3)
O20.048 (2)0.081 (3)0.069 (3)0.010 (2)0.014 (2)0.010 (3)
O30.055 (3)0.057 (3)0.051 (3)0.004 (2)0.002 (2)0.014 (2)
O40.085 (3)0.098 (4)0.058 (3)0.006 (3)0.026 (3)0.001 (3)
O50.069 (3)0.063 (3)0.046 (3)0.004 (2)0.001 (2)0.013 (2)
O60.059 (3)0.073 (3)0.055 (3)0.017 (2)0.008 (2)0.017 (2)
O70.053 (3)0.075 (3)0.071 (3)0.019 (2)0.008 (2)0.004 (2)
N10.044 (3)0.042 (3)0.041 (3)0.000 (2)0.001 (2)0.006 (2)
N20.052 (3)0.060 (3)0.045 (3)0.000 (3)0.009 (3)0.001 (3)
C30.046 (3)0.049 (3)0.042 (4)0.001 (3)0.002 (3)0.003 (3)
C40.045 (3)0.046 (3)0.041 (4)0.004 (3)0.002 (3)0.000 (3)
C50.042 (3)0.043 (3)0.040 (4)0.005 (3)0.002 (3)0.000 (3)
C60.044 (3)0.043 (3)0.044 (4)0.005 (3)0.006 (3)0.001 (3)
C70.046 (3)0.043 (3)0.047 (4)0.004 (3)0.004 (3)0.000 (3)
C80.061 (4)0.065 (4)0.046 (4)0.011 (4)0.006 (3)0.001 (3)
C90.085 (5)0.077 (5)0.052 (4)0.013 (4)0.001 (4)0.009 (4)
C100.046 (3)0.052 (4)0.069 (5)0.006 (3)0.014 (3)0.001 (4)
C110.049 (4)0.056 (4)0.084 (5)0.010 (3)0.005 (4)0.004 (4)
C120.056 (4)0.054 (4)0.067 (5)0.008 (3)0.001 (4)0.006 (3)
C130.045 (3)0.046 (3)0.045 (4)0.005 (3)0.002 (3)0.003 (3)
C140.056 (4)0.040 (3)0.053 (4)0.009 (3)0.006 (3)0.004 (3)
C150.040 (3)0.052 (4)0.044 (4)0.002 (3)0.005 (3)0.004 (3)
C160.049 (4)0.048 (3)0.053 (4)0.004 (3)0.008 (3)0.004 (3)
C170.048 (3)0.043 (3)0.049 (4)0.003 (3)0.002 (3)0.004 (3)
C180.054 (4)0.072 (4)0.062 (5)0.002 (3)0.001 (4)0.019 (4)
C190.104 (6)0.129 (7)0.071 (6)0.023 (5)0.010 (5)0.036 (5)
C200.036 (3)0.049 (3)0.066 (5)0.005 (3)0.001 (3)0.004 (3)
C210.050 (4)0.101 (6)0.080 (6)0.016 (4)0.012 (4)0.001 (4)
C220.049 (4)0.062 (4)0.049 (4)0.001 (3)0.006 (3)0.004 (3)
C230.050 (4)0.057 (4)0.047 (4)0.000 (3)0.000 (3)0.008 (3)
C240.089 (6)0.089 (5)0.066 (5)0.020 (4)0.005 (4)0.029 (4)
Cl10.143 (2)0.0998 (18)0.176 (3)0.0013 (17)0.000 (2)0.0064 (19)
C10.130 (8)0.130 (8)0.129 (13)0.038 (10)0.012 (8)0.012 (8)
Cl20.141 (2)0.201 (3)0.233 (4)0.062 (2)0.057 (3)0.117 (3)
C20.081 (5)0.081 (5)0.150 (13)0.004 (7)0.028 (6)0.028 (6)
Geometric parameters (Å, º) top
S1—O11.429 (5)C11—C121.386 (9)
S1—O21.435 (4)C12—H120.9300
S1—C31.767 (5)C12—C131.381 (8)
S1—C241.748 (6)C13—C141.477 (8)
O3—C51.220 (6)C15—C161.393 (8)
O4—C81.217 (7)C15—C231.376 (7)
O5—C141.213 (7)C16—H160.9300
O6—C171.365 (7)C16—C171.388 (7)
O6—C181.427 (7)C17—C201.409 (8)
O7—C201.370 (6)C18—H18A0.9700
O7—C211.428 (7)C18—H18B0.9700
N1—C41.481 (7)C18—C191.496 (8)
N1—C51.386 (6)C19—H19A0.9600
N1—C141.392 (7)C19—H19B0.9600
N2—H20.8597C19—H19C0.9600
N2—C71.398 (7)C20—C221.379 (8)
N2—C81.374 (8)C21—H21A0.9600
C3—H3A0.9700C21—H21B0.9600
C3—H3B0.9700C21—H21C0.9600
C3—C41.529 (7)C22—H220.9300
C4—H40.9800C22—C231.395 (8)
C4—C151.520 (8)C23—H230.9300
C5—C61.478 (8)C24—H24A0.9600
C6—C71.379 (8)C24—H24B0.9600
C6—C131.380 (7)C24—H24C0.9600
C7—C101.402 (8)Cl1—C11.726 (8)
C8—C91.484 (9)C1—Cl1i1.726 (8)
C9—H9A0.9600C1—H1A0.9700
C9—H9B0.9600C1—H1B0.9700
C9—H9C0.9600Cl2—C21.706 (7)
C10—H100.9300C2—Cl2ii1.706 (7)
C10—C111.371 (9)C2—H2A0.9700
C11—H110.9300C2—H2B0.9700
O1—S1—O2117.7 (3)O5—C14—C13128.9 (6)
O1—S1—C3108.9 (3)N1—C14—C13107.1 (5)
O1—S1—C24109.8 (3)C16—C15—C4122.7 (5)
O2—S1—C3108.5 (3)C23—C15—C4118.4 (5)
O2—S1—C24108.4 (3)C23—C15—C16119.0 (5)
C24—S1—C3102.4 (3)C15—C16—H16119.2
C17—O6—C18117.2 (4)C17—C16—C15121.5 (5)
C20—O7—C21116.8 (5)C17—C16—H16119.2
C5—N1—C4123.8 (5)O6—C17—C16125.5 (5)
C5—N1—C14110.4 (5)O6—C17—C20115.5 (5)
C14—N1—C4125.4 (5)C16—C17—C20118.9 (6)
C7—N2—H2115.5O6—C18—H18A110.1
C8—N2—H2115.1O6—C18—H18B110.1
C8—N2—C7129.4 (6)O6—C18—C19108.0 (5)
S1—C3—H3A108.8H18A—C18—H18B108.4
S1—C3—H3B108.8C19—C18—H18A110.1
H3A—C3—H3B107.7C19—C18—H18B110.1
C4—C3—S1113.9 (4)C18—C19—H19A109.5
C4—C3—H3A108.8C18—C19—H19B109.5
C4—C3—H3B108.8C18—C19—H19C109.5
N1—C4—C3111.4 (4)H19A—C19—H19B109.5
N1—C4—H4107.1H19A—C19—H19C109.5
N1—C4—C15112.3 (4)H19B—C19—H19C109.5
C3—C4—H4107.1O7—C20—C17115.5 (6)
C15—C4—C3111.5 (5)O7—C20—C22125.0 (6)
C15—C4—H4107.1C22—C20—C17119.4 (5)
O3—C5—N1125.1 (5)O7—C21—H21A109.5
O3—C5—C6127.9 (5)O7—C21—H21B109.5
N1—C5—C6107.0 (5)O7—C21—H21C109.5
C7—C6—C5130.9 (5)H21A—C21—H21B109.5
C7—C6—C13121.1 (5)H21A—C21—H21C109.5
C13—C6—C5107.9 (5)H21B—C21—H21C109.5
N2—C7—C10124.8 (6)C20—C22—H22119.6
C6—C7—N2118.0 (5)C20—C22—C23120.7 (6)
C6—C7—C10117.2 (6)C23—C22—H22119.6
O4—C8—N2122.7 (6)C15—C23—C22120.4 (6)
O4—C8—C9122.2 (6)C15—C23—H23119.8
N2—C8—C9115.1 (6)C22—C23—H23119.8
C8—C9—H9A109.5S1—C24—H24A109.5
C8—C9—H9B109.5S1—C24—H24B109.5
C8—C9—H9C109.5S1—C24—H24C109.5
H9A—C9—H9B109.5H24A—C24—H24B109.5
H9A—C9—H9C109.5H24A—C24—H24C109.5
H9B—C9—H9C109.5H24B—C24—H24C109.5
C7—C10—H10119.8Cl1—C1—Cl1i114.1 (8)
C11—C10—C7120.3 (6)Cl1i—C1—H1A108.7
C11—C10—H10119.8Cl1—C1—H1A108.7
C10—C11—H11118.5Cl1—C1—H1B108.7
C10—C11—C12123.1 (6)Cl1i—C1—H1B108.7
C12—C11—H11118.5H1A—C1—H1B107.6
C11—C12—H12122.1Cl2ii—C2—Cl2112.9 (7)
C13—C12—C11115.7 (6)Cl2ii—C2—H2A109.0
C13—C12—H12122.1Cl2—C2—H2A109.0
C6—C13—C12122.5 (6)Cl2ii—C2—H2B109.0
C6—C13—C14107.6 (5)Cl2—C2—H2B109.0
C12—C13—C14129.9 (6)H2A—C2—H2B107.8
O5—C14—N1124.1 (6)
S1—C3—C4—N160.0 (5)C7—N2—C8—O44.8 (10)
S1—C3—C4—C15173.7 (4)C7—N2—C8—C9173.4 (5)
O1—S1—C3—C460.3 (5)C7—C6—C13—C121.3 (9)
O2—S1—C3—C469.0 (5)C7—C6—C13—C14178.9 (5)
O3—C5—C6—C72.0 (10)C7—C10—C11—C121.5 (10)
O3—C5—C6—C13178.8 (5)C8—N2—C7—C6179.6 (6)
O6—C17—C20—O71.8 (8)C8—N2—C7—C100.2 (9)
O6—C17—C20—C22179.6 (5)C10—C11—C12—C131.3 (10)
O7—C20—C22—C23178.1 (5)C11—C12—C13—C60.1 (9)
N1—C4—C15—C16101.6 (6)C11—C12—C13—C14179.7 (6)
N1—C4—C15—C2379.5 (6)C12—C13—C14—O50.5 (10)
N1—C5—C6—C7178.1 (6)C12—C13—C14—N1179.8 (6)
N1—C5—C6—C131.2 (6)C13—C6—C7—N2178.2 (5)
N2—C7—C10—C11179.6 (5)C13—C6—C7—C101.2 (8)
C3—C4—C15—C1624.2 (8)C14—N1—C4—C353.7 (7)
C3—C4—C15—C23154.7 (5)C14—N1—C4—C1572.2 (7)
C4—N1—C5—O35.2 (8)C14—N1—C5—O3178.5 (5)
C4—N1—C5—C6174.8 (4)C14—N1—C5—C61.5 (6)
C4—N1—C14—O56.2 (9)C15—C16—C17—O6179.6 (5)
C4—N1—C14—C13174.4 (5)C15—C16—C17—C200.9 (8)
C4—C15—C16—C17177.6 (5)C16—C15—C23—C220.8 (9)
C4—C15—C23—C22178.1 (5)C16—C17—C20—O7178.7 (5)
C5—N1—C4—C3118.6 (6)C16—C17—C20—C220.1 (8)
C5—N1—C4—C15115.5 (5)C17—O6—C18—C19178.2 (6)
C5—N1—C14—O5179.4 (5)C17—C20—C22—C230.3 (9)
C5—N1—C14—C131.3 (6)C18—O6—C17—C160.3 (8)
C5—C6—C7—N20.9 (9)C18—O6—C17—C20179.8 (5)
C5—C6—C7—C10179.7 (5)C20—C22—C23—C150.0 (9)
C5—C6—C13—C12179.4 (5)C21—O7—C20—C17178.0 (5)
C5—C6—C13—C140.4 (6)C21—O7—C20—C223.5 (9)
C6—C7—C10—C110.2 (8)C23—C15—C16—C171.3 (9)
C6—C13—C14—O5179.8 (6)C24—S1—C3—C4176.5 (4)
C6—C13—C14—N10.5 (6)
Symmetry codes: (i) y, x, z+1; (ii) y+1, x+1, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O30.862.292.970 (6)136
C3—H3A···O5i0.972.293.155 (7)147
C3—H3A···O50.972.473.080 (7)121
C3—H3B···O4iii0.972.623.581 (8)170
C10—H10···O40.932.312.904 (8)121
C16—H16···O5i0.932.423.345 (7)179
C22—H22···O1iii0.932.523.432 (8)169
C24—H24A···O2i0.962.533.429 (9)156
C24—H24C···O3iv0.962.443.103 (7)126
Symmetry codes: (i) y, x, z+1; (iii) x+1/2, y+1/2, z+3/4; (iv) y+1/2, x1/2, z+1/4.
 

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