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In each of two isostructural 3-(5-ar­yloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(thio­phen-2-yl)prop-2-en-1-ones, the thio­phene unit is disordered over two sets of atomic sites and a combination of C—H...N and C—H...O hydrogen bonds link the mol­ecules into sheets.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S205698901901658X/zl2765sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205698901901658X/zl2765Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205698901901658X/zl2765IIsup3.hkl
Contains datablock II

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205698901901658X/zl2765Isup4.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205698901901658X/zl2765IIsup5.cml
Supplementary material

CCDC references: 1970925; 1970924

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in main residue
  • R factor = 0.042
  • wR factor = 0.117
  • Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ... -3.108 Report PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 2 Report
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 10 Note PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records 5 Report PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records 1 Report PLAT301_ALERT_3_G Main Residue Disorder ..............(Resd 1 ) 18% Note PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters 1 Info PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 10 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 7 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 5 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 8 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Datablock: II
Alert level C PLAT480_ALERT_4_C Long H...A H-Bond Reported H25 ..N32 . 2.69 Ang. PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ... -7.301 Report PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ... -0.457 Report
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 10 Note PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records 5 Report PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records 1 Report PLAT301_ALERT_3_G Main Residue Disorder ..............(Resd 1 ) 17% Note PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 10 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 1 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 3 ALERT level C = Check. Ensure it is not caused by an omission or oversight 6 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

For both structures, data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2017); data reduction: SAINT (Bruker, 2017); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b) and PLATON (Spek, 2009).

3-(3-Methyl-5-phenoxy-1-phenyl-1H-pyrazol-4-yl)-1-(thiophen-2-yl)prop-2-en-1-one (I) top
Crystal data top
C23H18N2O2SF(000) = 808
Mr = 386.45Dx = 1.296 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.6158 (5) ÅCell parameters from 3725 reflections
b = 19.8846 (11) Åθ = 2.1–25.6°
c = 10.3773 (6) ŵ = 0.18 mm1
β = 93.712 (2)°T = 296 K
V = 1980.04 (19) Å3Block, colourless
Z = 40.20 × 0.20 × 0.15 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
3725 independent reflections
Radiation source: fine-focus sealed tube2446 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
Detector resolution: 7.3910 pixels mm-1θmax = 25.6°, θmin = 2.1°
φ and ω scansh = 1011
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
k = 2424
Tmin = 0.941, Tmax = 0.973l = 1212
31970 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.042 w = 1/[σ2(Fo2) + (0.0467P)2 + 0.573P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.117(Δ/σ)max < 0.001
S = 1.06Δρmax = 0.20 e Å3
3725 reflectionsΔρmin = 0.14 e Å3
268 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
10 restraintsExtinction coefficient: 0.0059 (9)
Primary atom site location: difference Fourier map
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)
C10.6952 (2)0.38677 (11)0.5021 (2)0.0485 (5)
O10.76942 (19)0.43097 (8)0.55125 (17)0.0798 (6)
C20.5895 (2)0.40140 (11)0.3982 (2)0.0480 (5)
H20.53760.36630.36040.058*
C30.5660 (2)0.46399 (10)0.35662 (19)0.0451 (5)
H30.61750.49760.40000.054*
S110.82626 (11)0.29817 (5)0.67269 (8)0.0664 (3)0.844 (3)
C120.7111 (2)0.31696 (10)0.5460 (2)0.0484 (5)0.844 (3)
C130.6491 (14)0.2615 (5)0.5017 (13)0.0930 (17)0.844 (3)
H130.58370.26120.43160.112*0.844 (3)
C140.6904 (13)0.2030 (2)0.5695 (15)0.106 (3)0.844 (3)
H140.65470.16050.55060.128*0.844 (3)
C150.7865 (9)0.2158 (3)0.6639 (9)0.080 (2)0.844 (3)
H150.82700.18310.71850.096*0.844 (3)
S210.614 (2)0.2534 (7)0.484 (2)0.0930 (17)0.156 (3)
C220.7111 (2)0.31696 (10)0.5460 (2)0.0484 (5)0.156 (3)
C230.813 (2)0.2935 (10)0.626 (2)0.0664 (3)0.156 (3)
H230.88370.32050.66350.080*0.156 (3)
C240.805 (6)0.2239 (12)0.647 (6)0.080 (2)0.156 (3)
H240.85810.20090.71110.096*0.156 (3)
C250.713 (8)0.1950 (8)0.564 (9)0.106 (3)0.156 (3)
H250.70420.14880.55110.128*0.156 (3)
N310.31385 (16)0.49026 (8)0.08717 (15)0.0417 (4)
N320.36763 (17)0.55440 (8)0.09923 (17)0.0474 (4)
C330.4603 (2)0.55130 (10)0.1990 (2)0.0444 (5)
C340.4706 (2)0.48590 (10)0.25279 (19)0.0412 (5)
C350.3759 (2)0.44920 (9)0.17696 (18)0.0397 (5)
C3110.2118 (2)0.47606 (10)0.01477 (19)0.0400 (5)
C3120.1122 (2)0.42704 (10)0.0019 (2)0.0480 (5)
H3120.11130.40200.07370.058*
C3130.0143 (2)0.41552 (11)0.1021 (2)0.0555 (6)
H3130.05320.38260.09370.067*
C3140.0151 (2)0.45223 (12)0.2146 (2)0.0609 (7)
H3140.05080.44390.28220.073*
C3150.1141 (3)0.50138 (13)0.2260 (2)0.0596 (6)
H3150.11460.52660.30150.071*
C3160.2127 (2)0.51353 (11)0.1264 (2)0.0499 (5)
H3160.27940.54680.13450.060*
C3310.5426 (2)0.61231 (11)0.2386 (2)0.0609 (6)
H31A0.63530.60820.21020.091*
H31B0.54680.61650.33090.091*
H31C0.49870.65140.20010.091*
O350.35064 (14)0.38210 (6)0.17345 (13)0.0458 (4)
C3510.2722 (2)0.35338 (10)0.2680 (2)0.0445 (5)
C3520.2634 (3)0.28476 (12)0.2623 (3)0.0687 (7)
H3520.30950.26090.20090.082*
C3530.1856 (3)0.25194 (15)0.3483 (4)0.0947 (10)
H3530.17860.20530.34530.114*
C3540.1183 (3)0.28709 (17)0.4383 (4)0.0972 (11)
H3540.06560.26440.49650.117*
C3550.1281 (3)0.35565 (16)0.4432 (3)0.0854 (9)
H3550.08200.37930.50490.102*
C3560.2065 (2)0.39028 (12)0.3568 (2)0.0603 (6)
H3560.21380.43690.35940.072*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0522 (13)0.0469 (13)0.0450 (12)0.0042 (10)0.0060 (10)0.0003 (10)
O10.0919 (13)0.0535 (10)0.0872 (13)0.0176 (9)0.0475 (10)0.0094 (9)
C20.0493 (12)0.0441 (12)0.0491 (12)0.0035 (10)0.0085 (10)0.0002 (10)
C30.0465 (12)0.0443 (12)0.0437 (12)0.0051 (9)0.0022 (10)0.0015 (9)
S110.0811 (6)0.0537 (5)0.0608 (6)0.0027 (4)0.0243 (5)0.0092 (4)
C120.0550 (13)0.0451 (13)0.0442 (12)0.0012 (10)0.0038 (10)0.0002 (10)
C130.138 (7)0.048 (2)0.086 (4)0.017 (2)0.050 (3)0.004 (2)
C140.167 (6)0.0398 (17)0.104 (3)0.009 (3)0.050 (5)0.002 (3)
C150.113 (4)0.055 (2)0.070 (4)0.007 (2)0.016 (3)0.0186 (17)
S210.138 (7)0.048 (2)0.086 (4)0.017 (2)0.050 (3)0.004 (2)
C220.0550 (13)0.0451 (13)0.0442 (12)0.0012 (10)0.0038 (10)0.0002 (10)
C230.0811 (6)0.0537 (5)0.0608 (6)0.0027 (4)0.0243 (5)0.0092 (4)
C240.113 (4)0.055 (2)0.070 (4)0.007 (2)0.016 (3)0.0186 (17)
C250.167 (6)0.0398 (17)0.104 (3)0.009 (3)0.050 (5)0.002 (3)
N310.0402 (9)0.0369 (9)0.0473 (10)0.0007 (7)0.0034 (8)0.0033 (8)
N320.0489 (10)0.0350 (10)0.0571 (11)0.0031 (8)0.0054 (9)0.0051 (8)
C330.0428 (11)0.0390 (12)0.0509 (13)0.0024 (9)0.0002 (10)0.0011 (10)
C340.0393 (11)0.0401 (11)0.0437 (11)0.0002 (9)0.0002 (9)0.0016 (9)
C350.0393 (11)0.0345 (11)0.0450 (11)0.0012 (9)0.0016 (9)0.0022 (9)
C3110.0372 (11)0.0397 (11)0.0425 (11)0.0050 (9)0.0028 (9)0.0025 (9)
C3120.0471 (12)0.0425 (12)0.0534 (13)0.0040 (10)0.0045 (10)0.0020 (10)
C3130.0485 (13)0.0508 (14)0.0655 (15)0.0010 (11)0.0082 (11)0.0108 (12)
C3140.0554 (14)0.0677 (16)0.0570 (15)0.0127 (13)0.0149 (11)0.0184 (13)
C3150.0631 (15)0.0706 (16)0.0441 (13)0.0090 (13)0.0037 (12)0.0026 (11)
C3160.0473 (12)0.0552 (14)0.0470 (13)0.0025 (10)0.0016 (10)0.0025 (10)
C3310.0622 (15)0.0451 (13)0.0738 (16)0.0077 (11)0.0082 (12)0.0016 (12)
O350.0525 (9)0.0332 (8)0.0515 (9)0.0010 (6)0.0036 (7)0.0004 (6)
C3510.0411 (11)0.0398 (12)0.0515 (13)0.0025 (9)0.0047 (10)0.0105 (10)
C3520.0714 (16)0.0420 (14)0.093 (2)0.0053 (12)0.0095 (15)0.0076 (13)
C3530.094 (2)0.0543 (17)0.138 (3)0.0114 (16)0.023 (2)0.0266 (19)
C3540.093 (2)0.087 (2)0.115 (3)0.0112 (18)0.027 (2)0.046 (2)
C3550.086 (2)0.095 (2)0.0777 (19)0.0017 (17)0.0287 (16)0.0142 (17)
C3560.0628 (15)0.0546 (14)0.0640 (15)0.0025 (12)0.0093 (12)0.0034 (12)
Geometric parameters (Å, º) top
C1—O11.223 (2)C35—O351.356 (2)
C1—C21.462 (3)C311—C3161.378 (3)
C1—C121.466 (3)C311—C3121.379 (3)
C2—C31.332 (3)C312—C3131.376 (3)
C2—H20.9300C312—H3120.9300
C3—C341.437 (3)C313—C3141.377 (3)
C3—H30.9300C313—H3130.9300
S11—C151.684 (5)C314—C3151.375 (3)
S11—C121.705 (2)C314—H3140.9300
C12—C131.322 (7)C315—C3161.378 (3)
C13—C141.402 (10)C315—H3150.9300
C13—H130.9300C316—H3160.9300
C14—C151.327 (5)C331—H31A0.9600
C14—H140.9300C331—H31B0.9600
C15—H150.9300C331—H31C0.9600
S21—C251.685 (12)O35—C3511.398 (2)
C23—C241.404 (14)C351—C3561.365 (3)
C23—H230.9300C351—C3521.368 (3)
C24—C251.329 (9)C352—C3531.366 (4)
C24—H240.9300C352—H3520.9300
C25—H250.9300C353—C3541.364 (4)
N31—C351.349 (2)C353—H3530.9300
N31—N321.379 (2)C354—C3551.367 (4)
N31—C3111.424 (2)C354—H3540.9300
N32—C331.323 (3)C355—C3561.391 (3)
C33—C341.416 (3)C355—H3550.9300
C33—C3311.492 (3)C356—H3560.9300
C34—C351.374 (3)
O1—C1—C2121.57 (19)C316—C311—N31118.45 (18)
O1—C1—C12120.34 (19)C312—C311—N31121.18 (18)
C2—C1—C12118.09 (18)C313—C312—C311119.4 (2)
C3—C2—C1121.35 (19)C313—C312—H312120.3
C3—C2—H2119.3C311—C312—H312120.3
C1—C2—H2119.3C312—C313—C314120.7 (2)
C2—C3—C34127.83 (19)C312—C313—H313119.6
C2—C3—H3116.1C314—C313—H313119.6
C34—C3—H3116.1C315—C314—C313119.5 (2)
C15—S11—C1292.15 (19)C315—C314—H314120.3
C13—C12—C1130.3 (5)C313—C314—H314120.3
C13—C12—S11110.0 (5)C314—C315—C316120.4 (2)
C1—C12—S11119.77 (15)C314—C315—H315119.8
C12—C13—C14114.2 (6)C316—C315—H315119.8
C12—C13—H13122.9C315—C316—C311119.7 (2)
C14—C13—H13122.9C315—C316—H316120.2
C15—C14—C13111.9 (4)C311—C316—H316120.2
C15—C14—H14124.0C33—C331—H31A109.5
C13—C14—H14124.0C33—C331—H31B109.5
C14—C15—S11111.7 (4)H31A—C331—H31B109.5
C14—C15—H15124.1C33—C331—H31C109.5
S11—C15—H15124.1H31A—C331—H31C109.5
C24—C23—H23123.3H31B—C331—H31C109.5
C25—C24—C23111.4 (14)C35—O35—C351119.13 (15)
C25—C24—H24124.3C356—C351—C352122.3 (2)
C23—C24—H24124.3C356—C351—O35123.30 (19)
C24—C25—S21110.8 (12)C352—C351—O35114.3 (2)
C24—C25—H25124.6C353—C352—C351118.9 (3)
S21—C25—H25124.6C353—C352—H352120.5
C35—N31—N32110.54 (15)C351—C352—H352120.5
C35—N31—C311130.24 (16)C354—C353—C352120.4 (3)
N32—N31—C311119.16 (15)C354—C353—H353119.8
C33—N32—N31104.92 (15)C352—C353—H353119.8
N32—C33—C34112.18 (17)C353—C354—C355120.1 (3)
N32—C33—C331119.74 (18)C353—C354—H354119.9
C34—C33—C331128.03 (19)C355—C354—H354119.9
C35—C34—C33103.60 (17)C354—C355—C356120.6 (3)
C35—C34—C3129.46 (18)C354—C355—H355119.7
C33—C34—C3126.81 (18)C356—C355—H355119.7
N31—C35—O35120.45 (17)C351—C356—C355117.6 (2)
N31—C35—C34108.73 (17)C351—C356—H356121.2
O35—C35—C34130.44 (17)C355—C356—H356121.2
C316—C311—C312120.35 (19)
O1—C1—C2—C32.8 (3)C33—C34—C35—N310.8 (2)
C12—C1—C2—C3177.6 (2)C3—C34—C35—N31176.83 (19)
C1—C2—C3—C34177.2 (2)C33—C34—C35—O35172.0 (2)
O1—C1—C12—C13175.3 (10)C3—C34—C35—O354.1 (4)
C2—C1—C12—C134.3 (11)C35—N31—C311—C316148.8 (2)
O1—C1—C12—S114.0 (3)N32—N31—C311—C31627.9 (3)
C2—C1—C12—S11176.40 (16)C35—N31—C311—C31232.6 (3)
C15—S11—C12—C130.6 (9)N32—N31—C311—C312150.69 (18)
C15—S11—C12—C1180.0 (4)C316—C311—C312—C3130.5 (3)
C1—C12—C13—C14179.5 (10)N31—C311—C312—C313179.09 (18)
S11—C12—C13—C141.1 (17)C311—C312—C313—C3140.2 (3)
C12—C13—C14—C151 (2)C312—C313—C314—C3150.7 (3)
C13—C14—C15—S110.7 (17)C313—C314—C315—C3160.6 (3)
C12—S11—C15—C140.1 (11)C314—C315—C316—C3110.1 (3)
C23—C24—C25—S2112 (9)C312—C311—C316—C3150.6 (3)
C35—N31—N32—C331.3 (2)N31—C311—C316—C315179.25 (18)
C311—N31—N32—C33178.64 (17)N31—C35—O35—C351109.5 (2)
N31—N32—C33—C340.8 (2)C34—C35—O35—C35178.5 (3)
N31—N32—C33—C331178.55 (18)C35—O35—C351—C3567.1 (3)
N32—C33—C34—C350.0 (2)C35—O35—C351—C352174.51 (18)
C331—C33—C34—C35177.6 (2)C356—C351—C352—C3530.2 (4)
N32—C33—C34—C3176.16 (19)O35—C351—C352—C353178.2 (2)
C331—C33—C34—C31.4 (4)C351—C352—C353—C3540.1 (5)
C2—C3—C34—C354.2 (4)C352—C353—C354—C3550.0 (5)
C2—C3—C34—C33171.0 (2)C353—C354—C355—C3560.0 (5)
N32—N31—C35—O35172.30 (16)C352—C351—C356—C3550.2 (4)
C311—N31—C35—O354.7 (3)O35—C351—C356—C355178.1 (2)
N32—N31—C35—C341.3 (2)C354—C355—C356—C3510.0 (4)
C311—N31—C35—C34178.29 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14···N32i0.932.623.462 (9)151
C25—H25···N32i0.932.513.33 (5)148
C314—H314···O1ii0.932.383.305 (3)175
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x1, y, z1.
3-[3-Methyl-5-(2-methylphenoxy)-1-phenyl-1H-pyrazol-4-yl]-1-(thiophen-2-yl)prop-2-en-1-one (II) top
Crystal data top
C24H20N2O2SF(000) = 840
Mr = 400.48Dx = 1.294 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.4336 (4) ÅCell parameters from 5216 reflections
b = 20.6071 (9) Åθ = 2.0–28.6°
c = 10.5866 (4) ŵ = 0.18 mm1
β = 93.106 (2)°T = 296 K
V = 2055.00 (15) Å3Block, colourless
Z = 40.30 × 0.20 × 0.15 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
4735 independent reflections
Radiation source: fine-focus sealed tube2877 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
Detector resolution: 7.3910 pixels mm-1θmax = 27.6°, θmin = 2.0°
φ and ω scansh = 1211
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
k = 2626
Tmin = 0.926, Tmax = 0.973l = 1311
35938 measured reflections
Refinement top
Refinement on F2Primary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.142 w = 1/[σ2(Fo2) + (0.0624P)2 + 0.5761P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
4735 reflectionsΔρmax = 0.19 e Å3
277 parametersΔρmin = 0.23 e Å3
10 restraints
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)
C10.6834 (2)0.38495 (10)0.49061 (18)0.0484 (5)
O10.75006 (19)0.42752 (8)0.54834 (16)0.0747 (5)
C20.5798 (2)0.39981 (10)0.38620 (18)0.0484 (5)
H20.53020.36610.34550.058*
C30.5555 (2)0.46061 (10)0.34871 (18)0.0464 (5)
H30.60470.49260.39490.056*
S110.81442 (11)0.29803 (4)0.65506 (8)0.0669 (3)0.883 (2)
C120.7062 (2)0.31666 (10)0.52477 (17)0.0456 (5)0.883 (2)
C130.6609 (8)0.2617 (3)0.4682 (5)0.0603 (9)0.883 (2)
H130.60010.26160.39610.072*0.883 (2)
C140.7118 (5)0.20428 (17)0.5259 (4)0.0643 (12)0.883 (2)
H140.69120.16270.49610.077*0.883 (2)
C150.7941 (9)0.21758 (17)0.6295 (6)0.0671 (16)0.883 (2)
H150.83570.18590.68190.080*0.883 (2)
S210.6339 (18)0.2553 (6)0.4380 (13)0.0603 (9)0.117 (2)
C220.7062 (2)0.31666 (10)0.52477 (17)0.0456 (5)0.117 (2)
C230.784 (3)0.2933 (10)0.623 (2)0.0669 (3)0.117 (2)
H230.83960.31950.67770.080*0.117 (2)
C240.775 (8)0.2255 (11)0.638 (5)0.0671 (16)0.117 (2)
H240.82520.20180.70110.080*0.117 (2)
C250.685 (5)0.2001 (8)0.550 (3)0.0643 (12)0.117 (2)
H250.65440.15730.54940.077*0.117 (2)
N310.30777 (16)0.48865 (7)0.08120 (15)0.0431 (4)
N320.36119 (18)0.55036 (8)0.09699 (16)0.0492 (4)
C330.4529 (2)0.54660 (9)0.19571 (19)0.0469 (5)
C340.4627 (2)0.48304 (9)0.24567 (18)0.0430 (4)
C350.36867 (19)0.44824 (9)0.16871 (17)0.0405 (4)
C3110.20793 (19)0.47603 (9)0.02174 (18)0.0419 (4)
C3120.1090 (2)0.42664 (10)0.0158 (2)0.0495 (5)
H3120.10620.40090.05620.059*
C3130.0145 (2)0.41597 (11)0.1180 (2)0.0580 (6)
H3130.05150.38260.11470.070*
C3140.0169 (2)0.45393 (12)0.2241 (2)0.0624 (6)
H3140.04690.44620.29260.075*
C3150.1140 (2)0.50340 (13)0.2289 (2)0.0621 (6)
H3150.11540.52940.30060.075*
C3160.2098 (2)0.51483 (11)0.12766 (19)0.0506 (5)
H3160.27510.54850.13110.061*
C3310.5357 (3)0.60493 (10)0.2386 (2)0.0625 (6)
H31A0.63180.60080.21420.094*
H31B0.53490.60850.32900.094*
H31C0.49360.64300.20030.094*
O350.34553 (14)0.38351 (6)0.16246 (12)0.0470 (3)
C3510.2552 (2)0.35450 (10)0.24627 (19)0.0488 (5)
C3520.2429 (2)0.28766 (11)0.2301 (2)0.0614 (6)
C3530.1516 (3)0.25613 (15)0.3056 (3)0.0874 (10)
H3530.14040.21140.29770.105*
C3540.0766 (3)0.28876 (19)0.3921 (3)0.0949 (11)
H3540.01430.26610.44100.114*
C3550.0918 (3)0.35466 (17)0.4081 (3)0.0862 (9)
H3550.04110.37630.46810.103*
C3560.1842 (2)0.38895 (13)0.3332 (2)0.0656 (6)
H3560.19680.43350.34240.079*
C3570.3278 (3)0.25326 (12)0.1355 (3)0.0832 (9)
H35A0.42650.25460.16250.125*
H35B0.31410.27420.05470.125*
H35C0.29710.20890.12850.125*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0519 (12)0.0483 (12)0.0442 (11)0.0032 (10)0.0045 (9)0.0023 (9)
O10.0920 (12)0.0541 (9)0.0734 (10)0.0092 (9)0.0381 (9)0.0023 (8)
C20.0481 (11)0.0482 (12)0.0476 (11)0.0023 (9)0.0087 (9)0.0021 (9)
C30.0468 (11)0.0481 (12)0.0437 (11)0.0023 (9)0.0039 (9)0.0007 (9)
S110.0885 (6)0.0555 (4)0.0533 (5)0.0004 (4)0.0283 (3)0.0057 (3)
C120.0471 (11)0.0492 (11)0.0399 (10)0.0002 (9)0.0036 (8)0.0023 (9)
C130.071 (3)0.0556 (17)0.051 (3)0.0026 (16)0.0199 (18)0.0051 (17)
C140.079 (3)0.0449 (13)0.068 (2)0.0014 (13)0.004 (2)0.0002 (12)
C150.081 (3)0.0560 (16)0.0624 (19)0.0084 (19)0.008 (2)0.0112 (16)
S210.071 (3)0.0556 (17)0.051 (3)0.0026 (16)0.0199 (18)0.0051 (17)
C220.0471 (11)0.0492 (11)0.0399 (10)0.0002 (9)0.0036 (8)0.0023 (9)
C230.0885 (6)0.0555 (4)0.0533 (5)0.0004 (4)0.0283 (3)0.0057 (3)
C240.081 (3)0.0560 (16)0.0624 (19)0.0084 (19)0.008 (2)0.0112 (16)
C250.079 (3)0.0449 (13)0.068 (2)0.0014 (13)0.004 (2)0.0002 (12)
N310.0448 (9)0.0350 (8)0.0485 (9)0.0001 (7)0.0054 (7)0.0033 (7)
N320.0528 (10)0.0345 (9)0.0591 (10)0.0033 (7)0.0083 (8)0.0040 (8)
C330.0475 (11)0.0377 (10)0.0548 (12)0.0009 (9)0.0022 (9)0.0005 (9)
C340.0422 (10)0.0387 (10)0.0477 (11)0.0013 (8)0.0024 (8)0.0012 (8)
C350.0413 (10)0.0335 (10)0.0467 (11)0.0003 (8)0.0008 (8)0.0030 (8)
C3110.0391 (10)0.0402 (10)0.0458 (11)0.0067 (8)0.0027 (8)0.0022 (8)
C3120.0479 (11)0.0452 (11)0.0546 (12)0.0027 (9)0.0042 (9)0.0008 (9)
C3130.0506 (12)0.0577 (13)0.0643 (14)0.0000 (11)0.0091 (10)0.0109 (11)
C3140.0555 (13)0.0760 (16)0.0541 (14)0.0087 (12)0.0130 (10)0.0127 (12)
C3150.0601 (14)0.0776 (16)0.0479 (12)0.0094 (12)0.0039 (10)0.0072 (11)
C3160.0470 (11)0.0542 (13)0.0505 (12)0.0032 (10)0.0008 (9)0.0051 (10)
C3310.0679 (15)0.0413 (12)0.0766 (15)0.0052 (10)0.0124 (12)0.0050 (11)
O350.0492 (8)0.0340 (7)0.0575 (8)0.0018 (6)0.0006 (6)0.0031 (6)
C3510.0394 (10)0.0485 (12)0.0570 (12)0.0034 (9)0.0099 (9)0.0174 (10)
C3520.0555 (13)0.0484 (13)0.0770 (15)0.0111 (11)0.0283 (12)0.0223 (12)
C3530.0746 (18)0.0729 (19)0.111 (2)0.0286 (15)0.0290 (18)0.0405 (18)
C3540.0654 (18)0.108 (3)0.111 (3)0.0234 (18)0.0064 (17)0.059 (2)
C3550.0606 (16)0.116 (3)0.0831 (19)0.0065 (16)0.0130 (14)0.0311 (18)
C3560.0562 (14)0.0687 (16)0.0725 (15)0.0046 (12)0.0073 (12)0.0193 (13)
C3570.108 (2)0.0412 (13)0.097 (2)0.0010 (14)0.0277 (18)0.0037 (13)
Geometric parameters (Å, º) top
C1—O11.223 (2)C311—C3161.378 (3)
C1—C121.466 (3)C311—C3121.385 (3)
C1—C21.468 (3)C312—C3131.382 (3)
C2—C31.330 (3)C312—H3120.9300
C2—H20.9300C313—C3141.371 (3)
C3—C341.437 (3)C313—H3130.9300
C3—H30.9300C314—C3151.373 (3)
S11—C151.689 (4)C314—H3140.9300
S11—C121.7146 (19)C315—C3161.384 (3)
C12—C131.340 (5)C315—H3150.9300
C13—C141.404 (6)C316—H3160.9300
C13—H130.9300C331—H31A0.9600
C14—C151.337 (3)C331—H31B0.9600
C14—H140.9300C331—H31C0.9600
C15—H150.9300O35—C3511.397 (2)
S21—C251.692 (11)C351—C3561.367 (3)
C23—C241.408 (11)C351—C3521.392 (3)
C23—H230.9300C352—C3531.370 (4)
C24—C251.340 (9)C352—C3571.495 (4)
C24—H240.9300C353—C3541.364 (5)
C25—H250.9300C353—H3530.9300
N31—C351.351 (2)C354—C3551.375 (4)
N31—N321.375 (2)C354—H3540.9300
N31—C3111.425 (2)C355—C3561.400 (3)
N32—C331.322 (2)C355—H3550.9300
C33—C341.414 (3)C356—H3560.9300
C33—C3311.491 (3)C357—H35A0.9600
C34—C351.373 (3)C357—H35B0.9600
C35—O351.353 (2)C357—H35C0.9600
O1—C1—C12120.05 (18)C313—C312—H312120.4
O1—C1—C2121.99 (19)C311—C312—H312120.4
C12—C1—C2117.96 (17)C314—C313—C312120.9 (2)
C3—C2—C1121.21 (18)C314—C313—H313119.6
C3—C2—H2119.4C312—C313—H313119.6
C1—C2—H2119.4C313—C314—C315119.6 (2)
C2—C3—C34128.12 (19)C313—C314—H314120.2
C2—C3—H3115.9C315—C314—H314120.2
C34—C3—H3115.9C314—C315—C316120.4 (2)
C15—S11—C1291.91 (14)C314—C315—H315119.8
C13—C12—C1131.5 (3)C316—C315—H315119.8
C13—C12—S11109.4 (3)C311—C316—C315119.7 (2)
C1—C12—S11119.10 (15)C311—C316—H316120.2
C12—C13—C14115.1 (3)C315—C316—H316120.2
C12—C13—H13122.4C33—C331—H31A109.5
C14—C13—H13122.4C33—C331—H31B109.5
C15—C14—C13110.7 (3)H31A—C331—H31B109.5
C15—C14—H14124.6C33—C331—H31C109.5
C13—C14—H14124.6H31A—C331—H31C109.5
C14—C15—S11112.9 (3)H31B—C331—H31C109.5
C14—C15—H15123.6C35—O35—C351119.55 (16)
S11—C15—H15123.6C356—C351—C352123.8 (2)
C24—C23—H23122.8C356—C351—O35122.94 (19)
C25—C24—C23110.3 (12)C352—C351—O35113.3 (2)
C25—C24—H24124.9C353—C352—C351116.7 (3)
C23—C24—H24124.9C353—C352—C357122.8 (3)
C24—C25—S21112.0 (11)C351—C352—C357120.5 (2)
C24—C25—H25124.0C354—C353—C352121.5 (3)
S21—C25—H25124.0C354—C353—H353119.2
C35—N31—N32110.33 (15)C352—C353—H353119.2
C35—N31—C311130.62 (16)C353—C354—C355121.0 (3)
N32—N31—C311118.98 (15)C353—C354—H354119.5
C33—N32—N31105.17 (15)C355—C354—H354119.5
N32—C33—C34112.14 (17)C354—C355—C356119.5 (3)
N32—C33—C331120.20 (18)C354—C355—H355120.2
C34—C33—C331127.61 (18)C356—C355—H355120.2
C35—C34—C33103.57 (16)C351—C356—C355117.5 (3)
C35—C34—C3129.00 (18)C351—C356—H356121.2
C33—C34—C3127.36 (18)C355—C356—H356121.2
N31—C35—O35120.86 (16)C352—C357—H35A109.5
N31—C35—C34108.79 (16)C352—C357—H35B109.5
O35—C35—C34129.88 (17)H35A—C357—H35B109.5
C316—C311—C312120.13 (18)C352—C357—H35C109.5
C316—C311—N31118.65 (18)H35A—C357—H35C109.5
C312—C311—N31121.21 (17)H35B—C357—H35C109.5
C313—C312—C311119.3 (2)
O1—C1—C2—C31.0 (3)C3—C34—C35—N31177.55 (18)
C12—C1—C2—C3178.86 (19)C33—C34—C35—O35171.48 (19)
C1—C2—C3—C34177.23 (19)C3—C34—C35—O355.6 (3)
O1—C1—C12—C13170.9 (5)C35—N31—C311—C316150.6 (2)
C2—C1—C12—C139.0 (6)N32—N31—C311—C31625.9 (3)
O1—C1—C12—S116.0 (3)C35—N31—C311—C31230.5 (3)
C2—C1—C12—S11174.22 (15)N32—N31—C311—C312153.05 (18)
C15—S11—C12—C130.3 (5)C316—C311—C312—C3131.3 (3)
C15—S11—C12—C1177.8 (4)N31—C311—C312—C313179.78 (18)
C1—C12—C13—C14176.4 (4)C311—C312—C313—C3140.6 (3)
S11—C12—C13—C140.6 (7)C312—C313—C314—C3150.3 (3)
C12—C13—C14—C151.6 (9)C313—C314—C315—C3160.4 (3)
C13—C14—C15—S111.8 (9)C312—C311—C316—C3151.2 (3)
C12—S11—C15—C141.3 (7)N31—C311—C316—C315179.88 (18)
C23—C24—C25—S219 (8)C314—C315—C316—C3110.3 (3)
C35—N31—N32—C330.9 (2)N31—C35—O35—C351105.1 (2)
C311—N31—N32—C33178.00 (16)C34—C35—O35—C35183.7 (2)
N31—N32—C33—C340.6 (2)C35—O35—C351—C3562.2 (3)
N31—N32—C33—C331178.19 (19)C35—O35—C351—C352179.18 (16)
N32—C33—C34—C350.0 (2)C356—C351—C352—C3531.2 (3)
C331—C33—C34—C35177.5 (2)O35—C351—C352—C353177.45 (18)
N32—C33—C34—C3177.07 (18)C356—C351—C352—C357178.1 (2)
C331—C33—C34—C30.4 (4)O35—C351—C352—C3573.3 (3)
C2—C3—C34—C356.2 (4)C351—C352—C353—C3540.0 (4)
C2—C3—C34—C33170.2 (2)C357—C352—C353—C354179.3 (2)
N32—N31—C35—O35171.96 (16)C352—C353—C354—C3551.0 (4)
C311—N31—C35—O354.7 (3)C353—C354—C355—C3560.9 (4)
N32—N31—C35—C340.9 (2)C352—C351—C356—C3551.3 (3)
C311—N31—C35—C34177.56 (18)O35—C351—C356—C355177.17 (19)
C33—C34—C35—N310.5 (2)C354—C355—C356—C3510.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14···N32i0.932.553.483 (4)177
C25—H25···N32i0.932.693.47 (2)142
C314—H314···O1ii0.932.513.432 (3)171
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x1, y, z1.
 

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