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The heterocyclic portion of the tetra­hydro­iso­quinoline unit is planar and an intra­molecular N—H...N hydrogen bond and a C—H...π(ring) inter­action help to determine the overall conformation. In the crystal, O—H...O hydrogen bonds form inversion dimers, which are connected by C—H...O hydrogen bonds, forming layers parallel to (10\overline{1}).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989021000372/vm2243sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989021000372/vm2243Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989021000372/vm2243Isup3.cml
Supplementary material

CCDC reference: 2055318

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.032
  • wR factor = 0.083
  • Data-to-parameter ratio = 11.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT430_ALERT_2_C Short Inter D...A Contact O1 ..O1 . 2.88 Ang. 1-x,1-y,-z = 3_665 Check PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 12 Report
Alert level G PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check PLAT230_ALERT_2_G Hirshfeld Test Diff for C6 --C19 . 7.0 s.u. PLAT432_ALERT_2_G Short Inter X...Y Contact O3 ..C19 3.01 Ang. 1/2+x,3/2-y,1/2+z = 4_676 Check PLAT793_ALERT_4_G Model has Chirality at C1 (Centro SPGR) R Verify PLAT793_ALERT_4_G Model has Chirality at C2 (Centro SPGR) S Verify PLAT793_ALERT_4_G Model has Chirality at C3 (Centro SPGR) R Verify PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 58 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 14 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 9 ALERT level G = General information/check it is not something unexpected 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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
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

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL 2018/3 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

2-[(7-Acetyl-4-cyano-6-hydroxy-1,6-dimethyl-8-phenyl-5,6,7,8-tetrahydroisoquinolin-3-yl)sulfanyl]-N-phenylacetamide top
Crystal data top
C28H27N3O3SF(000) = 1024
Mr = 485.58Dx = 1.330 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54178 Å
a = 12.0487 (4) ÅCell parameters from 9855 reflections
b = 13.9821 (5) Åθ = 4.4–72.5°
c = 15.0239 (5) ŵ = 1.47 mm1
β = 106.606 (1)°T = 150 K
V = 2425.46 (14) Å3Column, colourless
Z = 40.26 × 0.14 × 0.08 mm
Data collection top
Bruker D8 VENTURE PHOTON 100 CMOS
diffractometer
4734 independent reflections
Radiation source: INCOATEC IµS micro–focus source4284 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.030
Detector resolution: 10.4167 pixels mm-1θmax = 72.4°, θmin = 4.4°
ω scansh = 1414
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
k = 1517
Tmin = 0.79, Tmax = 0.89l = 1718
18194 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032All H-atom parameters refined
wR(F2) = 0.083 w = 1/[σ2(Fo2) + (0.0386P)2 + 0.7971P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
4734 reflectionsΔρmax = 0.22 e Å3
425 parametersΔρmin = 0.21 e Å3
0 restraintsExtinction correction: SHELXL 2018/3 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: dualExtinction coefficient: 0.0039 (2)
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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.58184 (3)0.71687 (2)0.54963 (2)0.02702 (10)
O10.55415 (10)0.41602 (8)0.04888 (7)0.0389 (3)
O20.43190 (8)0.56327 (6)0.13750 (6)0.02221 (19)
H2A0.4361 (17)0.5558 (14)0.0816 (14)0.053 (5)*
O30.80915 (12)0.76450 (8)0.74784 (7)0.0463 (3)
N10.69752 (9)0.60562 (7)0.46015 (7)0.0226 (2)
N20.29604 (10)0.63554 (10)0.43743 (8)0.0363 (3)
N30.84869 (10)0.64010 (8)0.66349 (8)0.0276 (2)
H3A0.8267 (15)0.6163 (12)0.6064 (12)0.036 (4)*
C10.61831 (10)0.44233 (8)0.24855 (8)0.0192 (2)
H10.6482 (13)0.4819 (11)0.2084 (10)0.024 (4)*
C20.50155 (10)0.40139 (8)0.18906 (8)0.0201 (2)
H20.4796 (12)0.3479 (10)0.2233 (10)0.020 (3)*
C30.40183 (10)0.47505 (8)0.17204 (8)0.0195 (2)
C40.38587 (10)0.49849 (9)0.26679 (8)0.0198 (2)
H4A0.3566 (13)0.4409 (11)0.2914 (10)0.026 (4)*
H4B0.3263 (14)0.5499 (11)0.2593 (11)0.029 (4)*
C50.49669 (10)0.53100 (8)0.33547 (8)0.0184 (2)
C60.49119 (10)0.59248 (8)0.40793 (8)0.0203 (2)
C70.59357 (11)0.63014 (8)0.46686 (8)0.0211 (2)
C80.70418 (10)0.54452 (8)0.39243 (8)0.0217 (2)
C90.60604 (10)0.50545 (8)0.32793 (8)0.0190 (2)
C100.69924 (10)0.35759 (8)0.27879 (8)0.0207 (2)
C110.68696 (11)0.29760 (9)0.34899 (9)0.0260 (3)
H110.6323 (14)0.3128 (12)0.3811 (11)0.031 (4)*
C120.75677 (13)0.21739 (10)0.37340 (11)0.0376 (3)
H120.7497 (16)0.1783 (14)0.4238 (13)0.049 (5)*
C130.83774 (13)0.19569 (10)0.32770 (13)0.0425 (4)
H130.8869 (17)0.1427 (15)0.3467 (14)0.055 (5)*
C140.85014 (13)0.25445 (11)0.25757 (12)0.0401 (4)
H140.9087 (17)0.2423 (14)0.2239 (13)0.048 (5)*
C150.78155 (12)0.33535 (10)0.23292 (10)0.0305 (3)
H150.7883 (16)0.3783 (13)0.1832 (13)0.046 (5)*
C160.51833 (11)0.36283 (9)0.09888 (8)0.0265 (3)
C170.49321 (16)0.25966 (11)0.07668 (11)0.0392 (4)
H17A0.5448 (18)0.2227 (14)0.1245 (14)0.052 (5)*
H17B0.5020 (18)0.2458 (15)0.0139 (15)0.060 (6)*
H17C0.4129 (19)0.2421 (15)0.0793 (14)0.056 (6)*
C180.29017 (12)0.43558 (10)0.10695 (9)0.0268 (3)
H18A0.2702 (14)0.3705 (12)0.1262 (11)0.034 (4)*
H18B0.2960 (14)0.4305 (11)0.0429 (12)0.032 (4)*
H18C0.2254 (14)0.4804 (12)0.1047 (11)0.033 (4)*
C190.38188 (11)0.61752 (9)0.42231 (8)0.0242 (3)
C200.82558 (12)0.52338 (11)0.39007 (11)0.0325 (3)
H20A0.8471 (16)0.4556 (14)0.4093 (13)0.048 (5)*
H20B0.8298 (17)0.5294 (14)0.3262 (14)0.052 (5)*
H20C0.8796 (15)0.5671 (13)0.4323 (12)0.038 (4)*
C210.72565 (13)0.76893 (9)0.58406 (9)0.0289 (3)
H21A0.7616 (15)0.7601 (12)0.5336 (12)0.034 (4)*
H21B0.7122 (14)0.8361 (12)0.5963 (11)0.034 (4)*
C220.79955 (12)0.72541 (9)0.67374 (9)0.0284 (3)
C230.91089 (11)0.57882 (10)0.73536 (9)0.0262 (3)
C240.92081 (13)0.48300 (11)0.71326 (10)0.0331 (3)
H240.8859 (15)0.4621 (13)0.6506 (12)0.039 (4)*
C250.97905 (15)0.41944 (12)0.78136 (12)0.0416 (4)
H250.9834 (17)0.3516 (15)0.7626 (14)0.055 (5)*
C261.02900 (13)0.45021 (12)0.87153 (11)0.0388 (3)
H261.0692 (16)0.4050 (13)0.9198 (13)0.045 (5)*
C271.02052 (13)0.54563 (12)0.89285 (10)0.0351 (3)
H271.0570 (15)0.5694 (13)0.9570 (13)0.044 (5)*
C280.96158 (12)0.61022 (11)0.82593 (9)0.0304 (3)
H280.9531 (14)0.6768 (13)0.8419 (11)0.037 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.03021 (18)0.02522 (17)0.02499 (17)0.00004 (12)0.00686 (13)0.00720 (11)
O10.0576 (7)0.0405 (6)0.0222 (5)0.0128 (5)0.0172 (5)0.0055 (4)
O20.0282 (5)0.0208 (4)0.0193 (4)0.0033 (3)0.0096 (3)0.0042 (3)
O30.0735 (8)0.0346 (6)0.0253 (5)0.0090 (5)0.0050 (5)0.0072 (4)
N10.0235 (5)0.0207 (5)0.0229 (5)0.0007 (4)0.0055 (4)0.0007 (4)
N20.0281 (6)0.0549 (8)0.0271 (6)0.0031 (5)0.0096 (5)0.0098 (5)
N30.0293 (6)0.0301 (6)0.0211 (5)0.0012 (5)0.0037 (4)0.0048 (4)
C10.0219 (6)0.0191 (5)0.0182 (5)0.0013 (4)0.0081 (5)0.0023 (4)
C20.0238 (6)0.0189 (5)0.0170 (5)0.0027 (5)0.0050 (5)0.0012 (4)
C30.0219 (6)0.0193 (5)0.0170 (5)0.0019 (4)0.0052 (4)0.0015 (4)
C40.0196 (6)0.0227 (6)0.0176 (5)0.0008 (5)0.0061 (5)0.0006 (4)
C50.0218 (6)0.0169 (5)0.0169 (5)0.0003 (4)0.0062 (4)0.0036 (4)
C60.0223 (6)0.0206 (5)0.0186 (5)0.0018 (5)0.0068 (4)0.0017 (4)
C70.0267 (6)0.0185 (5)0.0182 (5)0.0007 (5)0.0063 (5)0.0019 (4)
C80.0221 (6)0.0198 (5)0.0232 (6)0.0004 (5)0.0066 (5)0.0008 (4)
C90.0220 (6)0.0167 (5)0.0189 (5)0.0011 (4)0.0070 (5)0.0024 (4)
C100.0199 (6)0.0193 (5)0.0218 (6)0.0008 (4)0.0043 (4)0.0026 (4)
C110.0250 (6)0.0261 (6)0.0243 (6)0.0016 (5)0.0028 (5)0.0034 (5)
C120.0354 (8)0.0261 (7)0.0415 (8)0.0009 (6)0.0049 (6)0.0092 (6)
C130.0294 (7)0.0235 (7)0.0632 (10)0.0078 (6)0.0053 (7)0.0087 (7)
C140.0268 (7)0.0372 (8)0.0558 (10)0.0051 (6)0.0109 (7)0.0174 (7)
C150.0273 (7)0.0316 (7)0.0355 (7)0.0020 (5)0.0134 (6)0.0055 (6)
C160.0286 (7)0.0300 (6)0.0183 (6)0.0114 (5)0.0024 (5)0.0000 (5)
C170.0491 (10)0.0322 (7)0.0328 (8)0.0075 (7)0.0062 (7)0.0112 (6)
C180.0248 (7)0.0293 (7)0.0232 (6)0.0008 (5)0.0021 (5)0.0040 (5)
C190.0270 (7)0.0285 (6)0.0171 (5)0.0007 (5)0.0062 (5)0.0035 (5)
C200.0209 (6)0.0347 (8)0.0412 (8)0.0030 (6)0.0075 (6)0.0113 (6)
C210.0362 (7)0.0226 (6)0.0257 (6)0.0055 (5)0.0055 (6)0.0021 (5)
C220.0337 (7)0.0254 (6)0.0245 (6)0.0065 (5)0.0060 (5)0.0031 (5)
C230.0196 (6)0.0333 (7)0.0261 (6)0.0030 (5)0.0071 (5)0.0016 (5)
C240.0313 (7)0.0354 (7)0.0314 (7)0.0014 (6)0.0069 (6)0.0060 (6)
C250.0431 (9)0.0369 (8)0.0443 (9)0.0078 (7)0.0116 (7)0.0006 (7)
C260.0348 (8)0.0468 (9)0.0349 (8)0.0091 (7)0.0101 (6)0.0084 (7)
C270.0294 (7)0.0492 (9)0.0262 (7)0.0012 (6)0.0073 (6)0.0006 (6)
C280.0283 (7)0.0358 (7)0.0263 (7)0.0038 (6)0.0065 (5)0.0032 (5)
Geometric parameters (Å, º) top
S1—C71.7712 (12)C11—H110.945 (17)
S1—C211.8132 (14)C12—C131.378 (2)
O1—C161.2203 (17)C12—H120.957 (19)
O2—C31.4245 (14)C13—C141.378 (3)
O2—H2A0.86 (2)C13—H130.94 (2)
O3—C221.2157 (17)C14—C151.387 (2)
N1—C71.3299 (16)C14—H140.99 (2)
N1—C81.3484 (16)C15—H150.980 (19)
N2—C191.1486 (17)C16—C171.492 (2)
N3—C221.3599 (18)C17—H17A0.96 (2)
N3—C231.4138 (17)C17—H17B1.00 (2)
N3—H3A0.887 (18)C17—H17C1.01 (2)
C1—C101.5192 (16)C18—H18A1.004 (17)
C1—C91.5244 (16)C18—H18B0.987 (17)
C1—C21.5450 (16)C18—H18C0.995 (17)
C1—H10.961 (15)C20—H20A1.00 (2)
C2—C161.5245 (16)C20—H20B0.98 (2)
C2—C31.5473 (16)C20—H20C0.981 (18)
C2—H20.986 (14)C21—C221.5141 (19)
C3—C181.5228 (17)C21—H21A0.982 (18)
C3—C41.5255 (16)C21—H21B0.980 (17)
C4—C51.5056 (16)C23—C241.394 (2)
C4—H4A0.992 (16)C23—C281.3938 (18)
C4—H4B0.999 (16)C24—C251.385 (2)
C5—C91.4006 (16)C24—H240.960 (18)
C5—C61.4034 (16)C25—C261.384 (2)
C6—C71.3995 (17)C25—H251.00 (2)
C6—C191.4374 (17)C26—C271.383 (2)
C8—C91.4074 (17)C26—H260.979 (19)
C8—C201.5026 (18)C27—C281.387 (2)
C10—C111.3882 (18)C27—H270.995 (18)
C10—C151.3949 (18)C28—H280.974 (18)
C11—C121.3869 (19)
C7—S1—C21102.34 (6)C12—C13—H13119.8 (12)
C3—O2—H2A110.0 (13)C13—C14—C15120.26 (14)
C7—N1—C8118.75 (11)C13—C14—H14122.4 (11)
C22—N3—C23126.73 (11)C15—C14—H14117.3 (11)
C22—N3—H3A114.8 (11)C14—C15—C10120.22 (14)
C23—N3—H3A117.3 (11)C14—C15—H15122.0 (11)
C10—C1—C9114.52 (9)C10—C15—H15117.8 (11)
C10—C1—C2106.53 (9)O1—C16—C17122.45 (13)
C9—C1—C2113.03 (10)O1—C16—C2119.45 (12)
C10—C1—H1108.2 (9)C17—C16—C2118.08 (12)
C9—C1—H1107.2 (9)C16—C17—H17A108.0 (12)
C2—C1—H1107.0 (9)C16—C17—H17B109.3 (12)
C16—C2—C1108.36 (10)H17A—C17—H17B112.5 (17)
C16—C2—C3112.49 (9)C16—C17—H17C111.2 (12)
C1—C2—C3112.62 (9)H17A—C17—H17C105.3 (16)
C16—C2—H2108.6 (8)H17B—C17—H17C110.6 (16)
C1—C2—H2108.4 (8)C3—C18—H18A112.6 (9)
C3—C2—H2106.2 (8)C3—C18—H18B110.8 (9)
O2—C3—C18110.48 (10)H18A—C18—H18B107.8 (13)
O2—C3—C4105.48 (9)C3—C18—H18C109.5 (9)
C18—C3—C4110.69 (10)H18A—C18—H18C109.3 (13)
O2—C3—C2111.73 (9)H18B—C18—H18C106.7 (13)
C18—C3—C2111.51 (10)N2—C19—C6177.04 (14)
C4—C3—C2106.72 (9)C8—C20—H20A110.6 (11)
C5—C4—C3112.38 (10)C8—C20—H20B109.3 (11)
C5—C4—H4A109.2 (9)H20A—C20—H20B106.3 (15)
C3—C4—H4A109.1 (9)C8—C20—H20C109.4 (10)
C5—C4—H4B109.1 (9)H20A—C20—H20C109.5 (15)
C3—C4—H4B109.2 (9)H20B—C20—H20C111.7 (15)
H4A—C4—H4B107.7 (12)C22—C21—S1111.32 (9)
C9—C5—C6118.23 (11)C22—C21—H21A111.0 (10)
C9—C5—C4122.55 (10)S1—C21—H21A109.0 (10)
C6—C5—C4119.16 (10)C22—C21—H21B107.8 (10)
C7—C6—C5119.52 (11)S1—C21—H21B104.0 (10)
C7—C6—C19119.54 (11)H21A—C21—H21B113.5 (13)
C5—C6—C19120.94 (11)O3—C22—N3124.57 (13)
N1—C7—C6122.27 (11)O3—C22—C21120.80 (13)
N1—C7—S1119.70 (9)N3—C22—C21114.59 (11)
C6—C7—S1117.97 (9)C24—C23—C28119.47 (13)
N1—C8—C9123.09 (11)C24—C23—N3117.61 (12)
N1—C8—C20114.24 (11)C28—C23—N3122.92 (12)
C9—C8—C20122.65 (11)C25—C24—C23120.04 (14)
C5—C9—C8118.03 (11)C25—C24—H24121.1 (11)
C5—C9—C1120.98 (10)C23—C24—H24118.9 (11)
C8—C9—C1120.87 (10)C26—C25—C24120.68 (15)
C11—C10—C15119.07 (12)C26—C25—H25122.0 (12)
C11—C10—C1119.99 (11)C24—C25—H25117.3 (12)
C15—C10—C1120.82 (11)C27—C26—C25119.10 (14)
C12—C11—C10120.08 (13)C27—C26—H26120.3 (11)
C12—C11—H11120.3 (10)C25—C26—H26120.6 (11)
C10—C11—H11119.6 (10)C26—C27—C28121.13 (14)
C13—C12—C11120.58 (15)C26—C27—H27120.4 (10)
C13—C12—H12120.3 (11)C28—C27—H27118.5 (11)
C11—C12—H12119.1 (12)C27—C28—C23119.57 (14)
C14—C13—C12119.79 (13)C27—C28—H28120.8 (10)
C14—C13—H13120.3 (12)C23—C28—H28119.6 (10)
C10—C1—C2—C1668.29 (11)C20—C8—C9—C12.86 (18)
C9—C1—C2—C16165.08 (9)C10—C1—C9—C5129.80 (11)
C10—C1—C2—C3166.61 (9)C2—C1—C9—C57.55 (15)
C9—C1—C2—C339.99 (13)C10—C1—C9—C854.15 (15)
C16—C2—C3—O271.57 (13)C2—C1—C9—C8176.41 (10)
C1—C2—C3—O251.24 (12)C9—C1—C10—C1149.93 (15)
C16—C2—C3—C1852.61 (14)C2—C1—C10—C1175.80 (13)
C1—C2—C3—C18175.42 (10)C9—C1—C10—C15134.18 (12)
C16—C2—C3—C4173.61 (10)C2—C1—C10—C15100.09 (13)
C1—C2—C3—C463.58 (12)C15—C10—C11—C120.68 (19)
O2—C3—C4—C564.66 (12)C1—C10—C11—C12176.64 (12)
C18—C3—C4—C5175.83 (10)C10—C11—C12—C130.8 (2)
C2—C3—C4—C554.32 (12)C11—C12—C13—C140.5 (2)
C3—C4—C5—C924.80 (15)C12—C13—C14—C150.1 (2)
C3—C4—C5—C6152.52 (10)C13—C14—C15—C100.2 (2)
C9—C5—C6—C73.36 (16)C11—C10—C15—C140.16 (19)
C4—C5—C6—C7174.07 (10)C1—C10—C15—C14176.09 (12)
C9—C5—C6—C19176.81 (11)C1—C2—C16—O157.14 (15)
C4—C5—C6—C195.76 (17)C3—C2—C16—O168.03 (15)
C8—N1—C7—C62.00 (17)C1—C2—C16—C17121.08 (13)
C8—N1—C7—S1175.41 (9)C3—C2—C16—C17113.75 (13)
C5—C6—C7—N13.85 (18)C7—S1—C21—C2298.03 (10)
C19—C6—C7—N1176.32 (11)C23—N3—C22—O35.2 (2)
C5—C6—C7—S1173.60 (9)C23—N3—C22—C21172.63 (12)
C19—C6—C7—S16.23 (15)S1—C21—C22—O396.36 (14)
C21—S1—C7—N113.60 (11)S1—C21—C22—N381.57 (14)
C21—S1—C7—C6163.92 (9)C22—N3—C23—C24158.95 (13)
C7—N1—C8—C90.24 (17)C22—N3—C23—C2820.9 (2)
C7—N1—C8—C20178.81 (11)C28—C23—C24—C251.0 (2)
C6—C5—C9—C81.26 (16)N3—C23—C24—C25178.86 (13)
C4—C5—C9—C8176.08 (10)C23—C24—C25—C260.7 (2)
C6—C5—C9—C1177.42 (10)C24—C25—C26—C270.3 (2)
C4—C5—C9—C10.08 (16)C25—C26—C27—C281.0 (2)
N1—C8—C9—C50.58 (17)C26—C27—C28—C230.6 (2)
C20—C8—C9—C5179.02 (12)C24—C23—C28—C270.4 (2)
N1—C8—C9—C1175.58 (10)N3—C23—C28—C27179.51 (13)
Hydrogen-bond geometry (Å, º) top
Cg3 is the centroid of the C10–C15 benzene ring.
D—H···AD—HH···AD···AD—H···A
O2—H2A···O1i0.86 (2)2.04 (2)2.8674 (13)161.9 (19)
N3—H3A···N10.887 (18)2.306 (18)3.1148 (15)151.6 (15)
C13—H13···O2ii0.94 (2)2.40 (2)3.2520 (19)150.5 (17)
C20—H20A···Cg31.00 (2)2.975 (19)3.6866 (16)128.7 (13)
Symmetry codes: (i) x+1, y+1, z; (ii) x+3/2, y1/2, z+1/2.
 

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