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The syntheses and crystal structures of three compounds, 2,2′-[(2-nitro­phen­yl)methyl­ene]bis­(3-hy­droxy-5,5-di­methyl­cyclo­hex-2-enone) (I), ethyl 4-(4-hy­droxy-3,5-di­meth­oxy­phen­yl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexa­hydro­quinoline-3-carboxyl­ate (II), and ethyl 4-(anthracen-9-yl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexa­hydro­quinoline-3-carboxyl­ate (III), are reported.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019017018/dx2021sup1.cif
Contains datablocks I, II, III, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989019017018/dx2021Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989019017018/dx2021Isup5.cml
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989019017018/dx2021IIsup3.hkl
Contains datablock II

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989019017018/dx2021IIsup6.cml
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989019017018/dx2021IIIsup4.hkl
Contains datablock III

CCDC references: 1973149; 1973148; 1973147

Key indicators

Structure: I
  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.054
  • wR factor = 0.154
  • Data-to-parameter ratio = 18.3
Structure: II
  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.001 Å
  • R factor = 0.039
  • wR factor = 0.108
  • Data-to-parameter ratio = 22.3
Structure: III
  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.048
  • wR factor = 0.135
  • Data-to-parameter ratio = 19.3

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level A PLAT707_ALERT_1_A D...A Calc 5.145(2), Rep 3.505(2), Dev.. 820.00 Sigma C15 -O5 1.555 1.565 ........ # 32 Check
Alert level B PLAT355_ALERT_3_B Long O-H (X0.82,N0.98A) O6 - H6 . 1.09 Ang.
Alert level C DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.58 Report PLAT097_ALERT_2_C Large Reported Max. (Positive) Residual Density 0.65 eA-3 PLAT222_ALERT_3_C NonSolvent Resd 1 H Uiso(max)/Uiso(min) Range 4.7 Ratio PLAT414_ALERT_2_C Short Intra D-H..H-X H6 ..H7 1.91 Ang. x,y,z = 1_555 Check PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 ..O1 . 2.63 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H10B ..O5 . 2.65 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H18B ..O1 . 2.67 Ang. PLAT761_ALERT_1_C CIF Contains no X-H Bonds ...................... Please Check PLAT762_ALERT_1_C CIF Contains no X-Y-H or H-Y-H Angles .......... Please Check
Alert level G PLAT726_ALERT_2_G H...A Calc 4.23000, Rep 2.58000 Dev... 1.65 Ang. H15B -O5 1.555 1.565 ........ # 32 Check PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ... 5 Note
1 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 10 ALERT level C = Check. Ensure it is not caused by an omission or oversight 2 ALERT level G = General information/check it is not something unexpected 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 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 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Datablock: II
Alert level A PLAT707_ALERT_1_A D...A Calc 42.563(2), Rep 3.5237(12), Dev.. 19519.65 Sigma C12A -O2A 1.555 4.455 ........ # 64 Check
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.56 Report PLAT480_ALERT_4_C Long H...A H-Bond Reported H7C ..O6B . 2.67 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H16D ..O4A . 2.65 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H7B ..O2A . 2.69 Ang. PLAT761_ALERT_1_C CIF Contains no X-H Bonds ...................... Please Check PLAT762_ALERT_1_C CIF Contains no X-Y-H or H-Y-H Angles .......... Please Check
Alert level G PLAT725_ALERT_2_G D-H Calc 11.24000, Rep 0.98000 Dev... 10.26 Ang. C12A -H12A 1.555 1.555 ........ # 64 Check PLAT726_ALERT_2_G H...A Calc 50.28000, Rep 2.60000 Dev... 47.68 Ang. H12A -O2A 1.555 4.455 ........ # 64 Check PLAT728_ALERT_1_G D-H..A Calc 42.00, Rep 157.00 Dev... 115.00 Degree C12A -H12A -O2A 1.555 1.555 4.455 # 96 Check PLAT793_ALERT_4_G Model has Chirality at C4A (Centro SPGR) R Verify PLAT793_ALERT_4_G Model has Chirality at C4B (Centro SPGR) R Verify PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ... 3 Note
1 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 6 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 4 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 0 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Datablock: III

Alert level B PLAT410_ALERT_2_B Short Intra H...H Contact H4 ..H27 . 1.88 Ang. x,y,z = 1_555 Check
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.43 Report PLAT220_ALERT_2_C NonSolvent Resd 1 C Ueq(max) / Ueq(min) Range 3.1 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for O2 --C14 . 5.2 s.u. PLAT480_ALERT_4_C Long H...A H-Bond Reported H13B ..O2 . 2.65 Ang. PLAT761_ALERT_1_C CIF Contains no X-H Bonds ...................... Please Check PLAT762_ALERT_1_C CIF Contains no X-Y-H or H-Y-H Angles .......... Please Check
Alert level G PLAT432_ALERT_2_G Short Inter X...Y Contact C21 ..C21 3.20 Ang. 1-x,1-y,-z = 3_665 Check PLAT793_ALERT_4_G Model has Chirality at C4 (Centro SPGR) R Verify PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ... 3 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 6 ALERT level C = Check. Ensure it is not caused by an omission or oversight 3 ALERT level G = General information/check it is not something unexpected 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

For all structures, data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

2,2'-[(2-Nitrophenyl)methylene]bis(3-hydroxy-5,5-dimethylcyclohex-2-enone) (I) top
Crystal data top
C23H27NO6Z = 2
Mr = 413.45F(000) = 440
Triclinic, P1Dx = 1.297 Mg m3
a = 8.7024 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.8709 (4) ÅCell parameters from 9400 reflections
c = 13.1621 (5) Åθ = 2.5–28.8°
α = 90.3822 (19)°µ = 0.09 mm1
β = 108.9608 (18)°T = 100 K
γ = 97.3571 (18)°Prism, yellow
V = 1059.08 (7) Å30.39 × 0.25 × 0.13 mm
Data collection top
Bruker SMART BREEZE CCD
diffractometer
Rint = 0.031
φ and ω scansθmax = 29.1°, θmin = 2.5°
29458 measured reflectionsh = 1111
5315 independent reflectionsk = 1313
4254 reflections with I > 2σ(I)l = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.054H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.154 w = 1/[σ2(Fo2) + (0.0841P)2 + 0.5356P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
5315 reflectionsΔρmax = 0.65 e Å3
291 parametersΔρmin = 0.25 e Å3
0 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*/Ueq
O50.04549 (13)0.40295 (11)0.15867 (9)0.0208 (2)
O30.21250 (13)0.20362 (12)0.17985 (9)0.0236 (3)
O40.68127 (15)0.53646 (13)0.29954 (11)0.0320 (3)
O60.50510 (15)0.73583 (13)0.29901 (10)0.0296 (3)
C90.11023 (18)0.52479 (16)0.18099 (11)0.0185 (3)
O20.61739 (15)0.30380 (15)0.47643 (10)0.0346 (3)
O10.50744 (18)0.09861 (14)0.41032 (11)0.0380 (3)
C160.44538 (19)0.37141 (16)0.25549 (12)0.0203 (3)
C80.27365 (18)0.56290 (16)0.25447 (11)0.0183 (3)
C70.37049 (18)0.45661 (15)0.31983 (11)0.0182 (3)
H70.4665540.5109010.3750980.022*
N10.49857 (19)0.21541 (16)0.43905 (11)0.0279 (3)
C100.0114 (2)0.63357 (17)0.12509 (13)0.0235 (3)
H10A0.1042250.6065430.1207250.028*
H10B0.0143140.6367670.0505740.028*
C170.36806 (18)0.25256 (16)0.19662 (12)0.0209 (3)
C130.34611 (19)0.69472 (17)0.25407 (12)0.0218 (3)
C60.28101 (18)0.36902 (16)0.38462 (11)0.0191 (3)
C210.61154 (19)0.42118 (18)0.26078 (13)0.0237 (3)
C180.4540 (2)0.15999 (18)0.14946 (14)0.0249 (3)
C120.2536 (2)0.80723 (17)0.20066 (13)0.0249 (3)
H12A0.2737240.8235720.1316420.030*
H12B0.2968540.8922380.2469280.030*
C110.0687 (2)0.77713 (16)0.17870 (13)0.0230 (3)
C10.3365 (2)0.25007 (17)0.43280 (12)0.0238 (3)
C20.2498 (2)0.16111 (18)0.48286 (13)0.0285 (4)
H20.2883040.0781280.5093120.034*
C40.0550 (2)0.31725 (19)0.45528 (13)0.0277 (4)
H40.0392750.3442840.4667570.033*
C190.6040 (2)0.23166 (18)0.12570 (14)0.0267 (4)
C140.0311 (2)0.78794 (18)0.28423 (14)0.0280 (4)
H14A0.0862460.7594170.2705620.042*
H14B0.0607340.8828210.3134480.042*
H14C0.0946980.7284980.3361440.042*
C50.13841 (19)0.40093 (17)0.40030 (12)0.0220 (3)
H50.0971290.4824170.3725020.026*
C200.7057 (2)0.3260 (2)0.22307 (15)0.0310 (4)
H20A0.7563930.2689570.2831960.037*
H20B0.7956690.3812630.2050320.037*
C30.1069 (2)0.19581 (19)0.49334 (14)0.0304 (4)
H3A0.0448320.1363390.5265470.036*
C220.7073 (2)0.1264 (2)0.10677 (18)0.0361 (4)
H22A0.7408860.0719410.1702620.054*
H22B0.8048720.1735970.0939040.054*
H22C0.6423130.0661010.0439890.054*
C150.0190 (2)0.87981 (19)0.10242 (15)0.0321 (4)
H15A0.0012190.8716200.0337630.048*
H15B0.0225490.9727260.1344280.048*
H15C0.1371910.8609840.0901110.048*
C230.5504 (3)0.3151 (2)0.02618 (16)0.0377 (4)
H23A0.4914400.2534000.0369190.057*
H23B0.6472920.3668410.0153460.057*
H23C0.4781640.3786620.0361900.057*
H30.160 (4)0.282 (3)0.187 (2)0.069 (9)*
H18A0.377 (3)0.114 (2)0.093 (2)0.042 (6)*
H18B0.486 (3)0.084 (2)0.2037 (19)0.042 (6)*
H60.569 (5)0.647 (4)0.307 (3)0.103 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O50.0178 (5)0.0222 (6)0.0217 (5)0.0004 (4)0.0066 (4)0.0023 (4)
O30.0172 (5)0.0246 (6)0.0287 (6)0.0011 (4)0.0089 (4)0.0045 (5)
O40.0232 (6)0.0310 (7)0.0418 (7)0.0051 (5)0.0142 (5)0.0105 (5)
O60.0217 (6)0.0284 (6)0.0351 (7)0.0051 (5)0.0080 (5)0.0042 (5)
C90.0194 (7)0.0225 (7)0.0163 (7)0.0031 (6)0.0095 (6)0.0003 (5)
O20.0232 (6)0.0471 (8)0.0292 (6)0.0049 (6)0.0029 (5)0.0016 (6)
O10.0496 (8)0.0338 (7)0.0369 (7)0.0206 (6)0.0170 (6)0.0081 (6)
C160.0182 (7)0.0224 (7)0.0216 (7)0.0027 (6)0.0083 (6)0.0001 (6)
C80.0177 (7)0.0213 (7)0.0167 (6)0.0027 (5)0.0068 (5)0.0018 (5)
C70.0163 (7)0.0209 (7)0.0172 (7)0.0005 (5)0.0061 (5)0.0027 (5)
N10.0304 (8)0.0335 (8)0.0209 (7)0.0114 (6)0.0070 (6)0.0047 (6)
C100.0233 (8)0.0249 (8)0.0202 (7)0.0034 (6)0.0043 (6)0.0017 (6)
C170.0178 (7)0.0246 (8)0.0211 (7)0.0024 (6)0.0075 (6)0.0004 (6)
C130.0210 (7)0.0249 (8)0.0203 (7)0.0007 (6)0.0095 (6)0.0032 (6)
C60.0185 (7)0.0236 (7)0.0143 (6)0.0000 (6)0.0054 (5)0.0029 (5)
C210.0181 (7)0.0310 (9)0.0213 (7)0.0006 (6)0.0068 (6)0.0029 (6)
C180.0211 (8)0.0265 (8)0.0280 (8)0.0008 (6)0.0103 (7)0.0065 (7)
C120.0299 (8)0.0208 (8)0.0260 (8)0.0003 (6)0.0135 (7)0.0017 (6)
C110.0278 (8)0.0218 (8)0.0210 (7)0.0052 (6)0.0095 (6)0.0034 (6)
C10.0234 (8)0.0280 (8)0.0186 (7)0.0048 (6)0.0044 (6)0.0028 (6)
C20.0382 (10)0.0257 (8)0.0194 (7)0.0022 (7)0.0072 (7)0.0019 (6)
C40.0255 (8)0.0383 (10)0.0210 (7)0.0000 (7)0.0115 (6)0.0012 (7)
C190.0241 (8)0.0288 (9)0.0311 (8)0.0032 (6)0.0144 (7)0.0028 (7)
C140.0333 (9)0.0289 (9)0.0278 (8)0.0079 (7)0.0166 (7)0.0018 (7)
C50.0224 (8)0.0264 (8)0.0179 (7)0.0037 (6)0.0076 (6)0.0005 (6)
C200.0176 (7)0.0369 (10)0.0395 (10)0.0011 (7)0.0128 (7)0.0102 (8)
C30.0365 (9)0.0335 (9)0.0222 (8)0.0030 (7)0.0142 (7)0.0013 (7)
C220.0283 (9)0.0356 (10)0.0493 (11)0.0062 (7)0.0190 (8)0.0077 (8)
C150.0384 (10)0.0259 (9)0.0312 (9)0.0091 (7)0.0084 (8)0.0071 (7)
C230.0470 (11)0.0377 (11)0.0379 (10)0.0098 (9)0.0254 (9)0.0049 (8)
Geometric parameters (Å, º) top
O5—C91.2507 (19)C17—C181.499 (2)
O3—C171.3234 (19)C13—C121.499 (2)
O4—C211.240 (2)C6—C11.404 (2)
O6—C131.3228 (19)C6—C51.395 (2)
C9—C81.437 (2)C21—C201.502 (2)
C9—C101.507 (2)C18—C191.528 (2)
O2—N11.227 (2)C12—C111.528 (2)
O1—N11.231 (2)C11—C141.533 (2)
C16—C71.529 (2)C11—C151.527 (2)
C16—C171.370 (2)C1—C21.391 (2)
C16—C211.445 (2)C2—C31.380 (3)
C8—C71.523 (2)C4—C51.389 (2)
C8—C131.372 (2)C4—C31.375 (3)
C7—C61.533 (2)C19—C201.526 (2)
N1—C11.470 (2)C19—C221.526 (2)
C10—C111.527 (2)C19—C231.526 (3)
O5—C9—C8122.69 (14)O4—C21—C16122.67 (15)
O5—C9—C10117.37 (13)O4—C21—C20118.99 (14)
C8—C9—C10119.93 (13)C16—C21—C20118.26 (15)
C17—C16—C7124.87 (14)C17—C18—C19114.49 (14)
C17—C16—C21119.05 (14)C13—C12—C11113.81 (13)
C21—C16—C7116.07 (13)C10—C11—C12107.37 (13)
C9—C8—C7121.06 (13)C10—C11—C14111.47 (14)
C13—C8—C9117.49 (14)C10—C11—C15109.11 (14)
C13—C8—C7121.00 (13)C12—C11—C14110.01 (14)
C16—C7—C6112.82 (12)C15—C11—C12110.07 (14)
C8—C7—C16113.54 (12)C15—C11—C14108.80 (14)
C8—C7—C6114.51 (12)C6—C1—N1121.11 (15)
O2—N1—O1124.15 (16)C2—C1—N1114.97 (15)
O2—N1—C1117.60 (14)C2—C1—C6123.83 (15)
O1—N1—C1118.19 (15)C3—C2—C1118.67 (16)
C9—C10—C11115.19 (13)C3—C4—C5120.92 (16)
O3—C17—C16123.87 (14)C20—C19—C18107.98 (14)
O3—C17—C18112.79 (14)C20—C19—C22109.38 (15)
C16—C17—C18123.25 (14)C22—C19—C18110.18 (15)
O6—C13—C8123.82 (15)C23—C19—C18110.18 (15)
O6—C13—C12112.72 (14)C23—C19—C20109.85 (16)
C8—C13—C12123.46 (14)C23—C19—C22109.26 (15)
C1—C6—C7122.42 (13)C4—C5—C6122.05 (15)
C5—C6—C7122.82 (14)C21—C20—C19114.88 (14)
C5—C6—C1114.76 (14)C4—C3—C2119.41 (16)
O5—C9—C8—C77.3 (2)C7—C6—C1—C2173.36 (14)
O5—C9—C8—C13165.07 (14)C7—C6—C5—C4177.16 (14)
O5—C9—C10—C11161.40 (13)N1—C1—C2—C3171.47 (15)
O3—C17—C18—C19156.51 (14)C10—C9—C8—C7174.32 (13)
O4—C21—C20—C19146.42 (16)C10—C9—C8—C1313.3 (2)
O6—C13—C12—C11162.31 (13)C17—C16—C7—C888.49 (18)
C9—C8—C7—C1678.45 (17)C17—C16—C7—C643.9 (2)
C9—C8—C7—C653.11 (18)C17—C16—C21—O4169.75 (16)
C9—C8—C13—O6164.77 (14)C17—C16—C21—C2013.6 (2)
C9—C8—C13—C1214.0 (2)C17—C18—C19—C2045.7 (2)
C9—C10—C11—C1249.40 (17)C17—C18—C19—C22165.08 (15)
C9—C10—C11—C1471.15 (18)C17—C18—C19—C2374.29 (19)
C9—C10—C11—C15168.67 (14)C13—C8—C7—C1693.69 (17)
O2—N1—C1—C651.4 (2)C13—C8—C7—C6134.75 (14)
O2—N1—C1—C2125.14 (16)C13—C12—C11—C1048.40 (17)
O1—N1—C1—C6131.16 (16)C13—C12—C11—C1473.07 (17)
O1—N1—C1—C252.2 (2)C13—C12—C11—C15167.05 (14)
C16—C7—C6—C135.67 (19)C6—C1—C2—C35.0 (2)
C16—C7—C6—C5144.27 (14)C21—C16—C7—C892.93 (16)
C16—C17—C18—C1926.7 (2)C21—C16—C7—C6134.69 (14)
C16—C21—C20—C1936.8 (2)C21—C16—C17—O3174.70 (14)
C8—C9—C10—C1120.2 (2)C21—C16—C17—C188.9 (2)
C8—C7—C6—C1167.58 (13)C18—C19—C20—C2151.4 (2)
C8—C7—C6—C512.4 (2)C1—C6—C5—C42.8 (2)
C8—C13—C12—C1118.8 (2)C1—C2—C3—C40.7 (2)
C7—C16—C17—O36.8 (3)C5—C6—C1—N1169.69 (14)
C7—C16—C17—C18169.69 (15)C5—C6—C1—C26.6 (2)
C7—C16—C21—O411.6 (2)C5—C4—C3—C24.3 (3)
C7—C16—C21—C20165.04 (15)C3—C4—C5—C62.5 (2)
C7—C8—C13—O67.6 (2)C22—C19—C20—C21171.31 (16)
C7—C8—C13—C12173.56 (14)C23—C19—C20—C2168.8 (2)
C7—C6—C1—N110.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O50.97 (3)1.62 (3)2.5570 (16)162 (3)
O6—H6···O41.08 (4)1.58 (4)2.6437 (19)166 (3)
C2—H2···O1i0.952.633.538 (2)160
C10—H10B···O5ii0.992.653.6138 (19)165
C15—H15B···O3iii0.982.583.505 (2)157
C18—H18B···O11.04 (2)2.67 (2)3.381 (2)125.5 (16)
C20—H20B···O5iv0.992.433.332 (2)152
Symmetry codes: (i) x+1, y, z+1; (ii) x, y+1, z; (iii) x, y+1, z; (iv) x+1, y, z.
Ethyl 4-(4-hydroxy-3,5-dimethoxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate (II) top
Crystal data top
C23H29NO6F(000) = 1776
Mr = 415.47Dx = 1.330 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.8854 (4) ÅCell parameters from 9684 reflections
b = 25.2446 (10) Åθ = 2.7–30.5°
c = 15.3665 (6) ŵ = 0.10 mm1
β = 100.7606 (19)°T = 100 K
V = 4148.4 (3) Å3Prism, colourless
Z = 80.48 × 0.43 × 0.31 mm
Data collection top
Bruker SMART BREEZE CCD
diffractometer
Rint = 0.045
φ and ω scansθmax = 30.6°, θmin = 1.6°
168826 measured reflectionsh = 1515
12707 independent reflectionsk = 3636
11044 reflections with I > 2σ(I)l = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.108 w = 1/[σ2(Fo2) + (0.060P)2 + 1.3541P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
12707 reflectionsΔρmax = 0.52 e Å3
569 parametersΔρmin = 0.20 e Å3
0 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*/Ueq
O1A0.09761 (6)0.68726 (3)0.28219 (5)0.01536 (13)
O2A0.66193 (6)0.61973 (3)0.32843 (5)0.01652 (13)
O3A0.54423 (6)0.69363 (3)0.31163 (5)0.01527 (13)
O4A0.40914 (7)0.74895 (3)0.70657 (5)0.01676 (14)
H4C0.4593 (16)0.7750 (7)0.7112 (11)0.035 (4)*
O5A0.31079 (7)0.65461 (3)0.68643 (4)0.01866 (14)
O6A0.47618 (6)0.80349 (3)0.56333 (5)0.01668 (14)
N1A0.34484 (7)0.54131 (3)0.39339 (5)0.01093 (13)
H1A0.3460 (13)0.5068 (6)0.4013 (9)0.021 (3)*
C2A0.45480 (8)0.56515 (3)0.38033 (5)0.01037 (15)
C3A0.45444 (8)0.61775 (3)0.36062 (6)0.01007 (14)
C4A0.33953 (8)0.65156 (3)0.36544 (5)0.00946 (14)
H4B0.3325670.6794210.3185050.011*
C5A0.22391 (8)0.61725 (3)0.34576 (5)0.00925 (14)
C6A0.10568 (8)0.63990 (3)0.30421 (5)0.00999 (14)
C7A0.00768 (8)0.60412 (3)0.28469 (6)0.01162 (15)
H7C0.0135010.5889370.2246620.014*
H7D0.0837390.6256170.2847130.014*
C8A0.00446 (8)0.55865 (3)0.35161 (6)0.01072 (15)
C9A0.11952 (8)0.52866 (3)0.35798 (6)0.01071 (15)
H9C0.1308110.5049440.4101760.013*
H9D0.1152820.5062530.3046260.013*
C10A0.23072 (8)0.56462 (3)0.36583 (5)0.00927 (14)
C11A0.01825 (9)0.58146 (4)0.44184 (6)0.01572 (17)
H11D0.0499140.6064780.4621310.024*
H11E0.0148410.5526010.4848880.024*
H11F0.0986350.5998540.4361320.024*
C12A0.11296 (9)0.52050 (4)0.31995 (7)0.01625 (17)
H12D0.1924030.5395840.3147120.024*
H12E0.1106120.4915810.3627710.024*
H12F0.1053060.5059200.2620950.024*
C13A0.56241 (8)0.52727 (4)0.38723 (6)0.01339 (16)
H13D0.5435030.4949670.4175710.020*
H13E0.6380140.5438010.4209130.020*
H13F0.5759970.5182860.3277030.020*
C14A0.56421 (8)0.64179 (4)0.33347 (6)0.01162 (15)
C15A0.63909 (9)0.71842 (4)0.27011 (6)0.01674 (17)
H15C0.7232060.7076230.3014640.020*
H15D0.6327450.7574220.2742560.020*
C16A0.62173 (10)0.70211 (4)0.17397 (7)0.02087 (19)
H16D0.6743310.7243030.1435330.031*
H16E0.5338310.7065700.1458510.031*
H16F0.6457600.6648930.1701670.031*
C17A0.35248 (8)0.67935 (3)0.45549 (6)0.01023 (15)
C18A0.32110 (8)0.65290 (3)0.52864 (6)0.01201 (15)
H18A0.2868180.6182260.5213740.014*
C19A0.33951 (8)0.67677 (4)0.61162 (6)0.01263 (16)
C20A0.39194 (8)0.72784 (4)0.62385 (6)0.01266 (16)
C21A0.42098 (8)0.75402 (3)0.55069 (6)0.01235 (16)
C22A0.40129 (8)0.73027 (3)0.46704 (6)0.01162 (15)
H22A0.4213640.7490090.4179340.014*
C23A0.25765 (10)0.60304 (4)0.67836 (7)0.02005 (19)
H23D0.1793410.6036520.6348940.030*
H23E0.2407150.5916040.7359080.030*
H23F0.3162500.5782940.6586940.030*
C24A0.38733 (10)0.84600 (4)0.54853 (7)0.02017 (19)
H24D0.3374790.8431720.4886240.030*
H24E0.4317360.8799530.5548670.030*
H24F0.3320680.8439130.5919770.030*
O1B0.64618 (7)0.56795 (3)0.59302 (5)0.01898 (14)
O2B0.42404 (7)0.61173 (3)0.93863 (5)0.02210 (15)
O3B0.47350 (6)0.54093 (3)0.86392 (5)0.01724 (14)
O4B1.07150 (7)0.47496 (3)0.91945 (5)0.01745 (14)
H41.1277 (17)0.4973 (7)0.9396 (12)0.040 (5)*
O5B1.09254 (6)0.57723 (3)0.88846 (5)0.01832 (14)
O6B0.85544 (7)0.42479 (3)0.88741 (5)0.01802 (14)
N1B0.67195 (7)0.70086 (3)0.81054 (5)0.01272 (14)
H10.6769 (13)0.7356 (6)0.8200 (9)0.022 (3)*
C2B0.60016 (8)0.67286 (4)0.86093 (6)0.01315 (16)
C3B0.57467 (8)0.62086 (4)0.84315 (6)0.01213 (15)
C4B0.63347 (8)0.59179 (3)0.77391 (6)0.01085 (15)
H4A0.5703910.5661450.7424800.013*
C5B0.66228 (8)0.63135 (3)0.70649 (6)0.01071 (15)
C6B0.66639 (8)0.61434 (3)0.61710 (6)0.01161 (15)
C7B0.69106 (8)0.65543 (3)0.55138 (6)0.01271 (15)
H7A0.6106420.6718730.5237440.015*
H7B0.7258840.6376500.5039290.015*
C8B0.78141 (8)0.69911 (3)0.59211 (6)0.01258 (15)
C9B0.73133 (8)0.72350 (3)0.67009 (6)0.01263 (15)
H9A0.7981260.7451080.7059250.015*
H9B0.6608840.7474370.6466160.015*
C10B0.68745 (8)0.68288 (3)0.72894 (6)0.01098 (15)
C11B0.91219 (9)0.67533 (4)0.62358 (7)0.01783 (18)
H11A0.9066850.6459160.6642970.027*
H11B0.9682280.7026190.6541580.027*
H11C0.9450070.6623030.5723590.027*
C12B0.78685 (10)0.74186 (4)0.52223 (7)0.01908 (18)
H12A0.8179870.7263050.4720810.029*
H12B0.8431310.7703220.5482820.029*
H12C0.7028980.7563060.5016000.029*
C13B0.55601 (10)0.70687 (4)0.92881 (7)0.02043 (19)
H13A0.6171410.7350370.9476640.031*
H13B0.5468650.6851610.9800880.031*
H13C0.4751270.7226650.9030900.031*
C14B0.48511 (8)0.59282 (4)0.88766 (6)0.01479 (16)
C15B0.37849 (9)0.51189 (4)0.89925 (7)0.01923 (18)
H15A0.2944550.5257950.8737050.023*
H15B0.3920240.5160620.9644090.023*
C16B0.38731 (10)0.45419 (4)0.87558 (7)0.02153 (19)
H16A0.3767400.4505550.8111170.032*
H16B0.3215670.4342090.8968280.032*
H16C0.4693510.4403250.9034270.032*
C17B0.75057 (8)0.56042 (3)0.81518 (6)0.01136 (15)
C18B0.86636 (8)0.58599 (4)0.83344 (6)0.01318 (16)
H180.8719980.6227990.8219190.016*
C19B0.97326 (8)0.55741 (4)0.86850 (6)0.01334 (16)
C20B0.96602 (8)0.50345 (4)0.88589 (6)0.01323 (16)
C21B0.85061 (9)0.47788 (3)0.86888 (6)0.01301 (16)
C22B0.74257 (8)0.50638 (4)0.83344 (6)0.01278 (16)
H220.6637720.4890240.8217670.015*
C23B1.10806 (9)0.63320 (4)0.88435 (8)0.02108 (19)
H23A1.0771970.6454850.8237120.032*
H23B1.1968970.6420700.9017950.032*
H23C1.0607430.6505160.9247180.032*
C24B0.74049 (10)0.39706 (4)0.88304 (7)0.01957 (19)
H24A0.6899460.4006740.8234900.029*
H24B0.6947460.4119350.9265590.029*
H24C0.7576870.3594980.8960710.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0138 (3)0.0100 (3)0.0212 (3)0.0012 (2)0.0004 (2)0.0044 (2)
O2A0.0114 (3)0.0183 (3)0.0206 (3)0.0018 (2)0.0049 (2)0.0016 (3)
O3A0.0153 (3)0.0116 (3)0.0209 (3)0.0018 (2)0.0086 (3)0.0018 (2)
O4A0.0174 (3)0.0172 (3)0.0155 (3)0.0066 (3)0.0026 (2)0.0073 (2)
O5A0.0266 (4)0.0172 (3)0.0127 (3)0.0096 (3)0.0049 (3)0.0020 (2)
O6A0.0150 (3)0.0086 (3)0.0256 (3)0.0037 (2)0.0018 (3)0.0039 (2)
N1A0.0099 (3)0.0076 (3)0.0152 (3)0.0012 (2)0.0019 (3)0.0017 (3)
C2A0.0098 (3)0.0115 (4)0.0096 (3)0.0008 (3)0.0012 (3)0.0006 (3)
C3A0.0088 (3)0.0107 (3)0.0106 (3)0.0002 (3)0.0017 (3)0.0005 (3)
C4A0.0087 (3)0.0078 (3)0.0117 (3)0.0001 (3)0.0014 (3)0.0002 (3)
C5A0.0088 (3)0.0084 (3)0.0104 (3)0.0001 (3)0.0016 (3)0.0004 (3)
C6A0.0101 (3)0.0097 (3)0.0102 (3)0.0007 (3)0.0020 (3)0.0005 (3)
C7A0.0095 (3)0.0113 (4)0.0134 (4)0.0005 (3)0.0004 (3)0.0006 (3)
C8A0.0096 (3)0.0098 (3)0.0130 (4)0.0010 (3)0.0027 (3)0.0007 (3)
C9A0.0102 (3)0.0081 (3)0.0138 (4)0.0010 (3)0.0024 (3)0.0005 (3)
C10A0.0095 (3)0.0092 (3)0.0090 (3)0.0005 (3)0.0014 (3)0.0003 (3)
C11A0.0166 (4)0.0174 (4)0.0146 (4)0.0002 (3)0.0064 (3)0.0019 (3)
C12A0.0119 (4)0.0147 (4)0.0220 (4)0.0042 (3)0.0026 (3)0.0009 (3)
C13A0.0118 (4)0.0126 (4)0.0159 (4)0.0035 (3)0.0031 (3)0.0003 (3)
C14A0.0113 (4)0.0126 (4)0.0107 (3)0.0014 (3)0.0015 (3)0.0008 (3)
C15A0.0160 (4)0.0162 (4)0.0195 (4)0.0051 (3)0.0072 (3)0.0022 (3)
C16A0.0203 (5)0.0245 (5)0.0190 (4)0.0016 (4)0.0066 (4)0.0024 (4)
C17A0.0086 (3)0.0089 (3)0.0130 (4)0.0004 (3)0.0014 (3)0.0009 (3)
C18A0.0124 (4)0.0098 (4)0.0136 (4)0.0019 (3)0.0020 (3)0.0013 (3)
C19A0.0124 (4)0.0120 (4)0.0135 (4)0.0022 (3)0.0024 (3)0.0008 (3)
C20A0.0104 (4)0.0123 (4)0.0149 (4)0.0013 (3)0.0015 (3)0.0040 (3)
C21A0.0100 (4)0.0082 (3)0.0185 (4)0.0016 (3)0.0017 (3)0.0027 (3)
C22A0.0107 (3)0.0091 (3)0.0150 (4)0.0004 (3)0.0023 (3)0.0003 (3)
C23A0.0280 (5)0.0149 (4)0.0177 (4)0.0065 (4)0.0052 (4)0.0013 (3)
C24A0.0219 (5)0.0102 (4)0.0281 (5)0.0000 (3)0.0039 (4)0.0003 (3)
O1B0.0299 (4)0.0093 (3)0.0169 (3)0.0001 (3)0.0023 (3)0.0026 (2)
O2B0.0220 (4)0.0223 (4)0.0258 (4)0.0014 (3)0.0142 (3)0.0004 (3)
O3B0.0148 (3)0.0159 (3)0.0229 (3)0.0016 (2)0.0082 (3)0.0013 (3)
O4B0.0143 (3)0.0165 (3)0.0203 (3)0.0059 (3)0.0001 (3)0.0028 (3)
O5B0.0112 (3)0.0149 (3)0.0272 (4)0.0005 (2)0.0007 (3)0.0011 (3)
O6B0.0181 (3)0.0111 (3)0.0256 (4)0.0029 (2)0.0060 (3)0.0060 (3)
N1B0.0151 (3)0.0098 (3)0.0137 (3)0.0001 (3)0.0038 (3)0.0031 (3)
C2B0.0121 (4)0.0147 (4)0.0128 (4)0.0025 (3)0.0027 (3)0.0008 (3)
C3B0.0101 (4)0.0136 (4)0.0129 (4)0.0022 (3)0.0026 (3)0.0010 (3)
C4B0.0107 (4)0.0095 (3)0.0123 (4)0.0011 (3)0.0017 (3)0.0001 (3)
C5B0.0105 (3)0.0094 (3)0.0119 (4)0.0012 (3)0.0014 (3)0.0003 (3)
C6B0.0113 (4)0.0099 (4)0.0128 (4)0.0016 (3)0.0001 (3)0.0009 (3)
C7B0.0147 (4)0.0114 (4)0.0117 (4)0.0004 (3)0.0017 (3)0.0008 (3)
C8B0.0127 (4)0.0122 (4)0.0131 (4)0.0004 (3)0.0032 (3)0.0011 (3)
C9B0.0143 (4)0.0093 (4)0.0147 (4)0.0006 (3)0.0037 (3)0.0013 (3)
C10B0.0098 (3)0.0107 (4)0.0122 (4)0.0015 (3)0.0014 (3)0.0011 (3)
C11B0.0133 (4)0.0205 (4)0.0197 (4)0.0007 (3)0.0032 (3)0.0036 (3)
C12B0.0230 (5)0.0174 (4)0.0177 (4)0.0045 (4)0.0061 (4)0.0020 (3)
C13B0.0250 (5)0.0196 (5)0.0191 (4)0.0027 (4)0.0105 (4)0.0044 (4)
C14B0.0122 (4)0.0162 (4)0.0162 (4)0.0020 (3)0.0030 (3)0.0030 (3)
C15B0.0148 (4)0.0195 (4)0.0252 (5)0.0026 (3)0.0082 (4)0.0042 (4)
C16B0.0210 (5)0.0193 (5)0.0244 (5)0.0038 (4)0.0046 (4)0.0020 (4)
C17B0.0117 (4)0.0108 (4)0.0116 (4)0.0020 (3)0.0023 (3)0.0005 (3)
C18B0.0131 (4)0.0106 (4)0.0152 (4)0.0014 (3)0.0012 (3)0.0006 (3)
C19B0.0118 (4)0.0138 (4)0.0140 (4)0.0009 (3)0.0012 (3)0.0016 (3)
C20B0.0138 (4)0.0139 (4)0.0119 (4)0.0046 (3)0.0021 (3)0.0008 (3)
C21B0.0166 (4)0.0107 (4)0.0126 (4)0.0028 (3)0.0049 (3)0.0016 (3)
C22B0.0135 (4)0.0120 (4)0.0134 (4)0.0015 (3)0.0041 (3)0.0004 (3)
C23B0.0156 (4)0.0162 (4)0.0307 (5)0.0016 (3)0.0025 (4)0.0033 (4)
C24B0.0213 (5)0.0145 (4)0.0243 (5)0.0009 (3)0.0078 (4)0.0041 (3)
Geometric parameters (Å, º) top
O1A—C6A1.2412 (10)O1B—C6B1.2355 (11)
O2A—C14A1.2159 (11)O2B—C14B1.2156 (12)
O3A—C14A1.3583 (11)O3B—C14B1.3593 (12)
O3A—C15A1.4529 (11)O3B—C15B1.4530 (11)
O4A—C20A1.3587 (11)O4B—C20B1.3713 (11)
O5A—C19A1.3661 (11)O5B—C19B1.3717 (11)
O5A—C23A1.4206 (12)O5B—C23B1.4257 (12)
O6A—C21A1.3837 (10)O6B—C21B1.3690 (11)
O6A—C24A1.4341 (12)O6B—C24B1.4245 (12)
N1A—C2A1.3874 (11)N1B—C2B1.3913 (12)
N1A—C10A1.3683 (11)N1B—C10B1.3733 (11)
C2A—C3A1.3617 (12)C2B—C3B1.3589 (13)
C2A—C13A1.5006 (12)C2B—C13B1.4979 (13)
C3A—C4A1.5275 (12)C3B—C4B1.5280 (12)
C3A—C14A1.4684 (12)C3B—C14B1.4725 (13)
C4A—C5A1.5112 (11)C4B—C5B1.5134 (12)
C4A—C17A1.5344 (12)C4B—C17B1.5337 (12)
C5A—C6A1.4437 (11)C5B—C6B1.4479 (12)
C5A—C10A1.3628 (11)C5B—C10B1.3604 (12)
C6A—C7A1.5134 (12)C6B—C7B1.5062 (12)
C7A—C8A1.5371 (12)C7B—C8B1.5314 (12)
C8A—C9A1.5346 (12)C8B—C9B1.5350 (12)
C8A—C11A1.5342 (12)C8B—C11B1.5374 (13)
C8A—C12A1.5313 (12)C8B—C12B1.5313 (13)
C9A—C10A1.4998 (11)C9B—C10B1.5027 (12)
C15A—C16A1.5111 (14)C15B—C16B1.5088 (15)
C17A—C18A1.4034 (12)C17B—C18B1.3972 (12)
C17A—C22A1.3895 (11)C17B—C22B1.3987 (12)
C18A—C19A1.3906 (12)C18B—C19B1.3896 (12)
C19A—C20A1.4082 (12)C19B—C20B1.3932 (13)
C20A—C21A1.3904 (13)C20B—C21B1.3931 (13)
C21A—C22A1.3981 (12)C21B—C22B1.3994 (12)
C14A—O3A—C15A115.43 (7)C14B—O3B—C15B115.02 (7)
C19A—O5A—C23A117.08 (7)C19B—O5B—C23B117.82 (7)
C21A—O6A—C24A113.00 (7)C21B—O6B—C24B118.16 (7)
C10A—N1A—C2A121.78 (7)C10B—N1B—C2B121.19 (8)
N1A—C2A—C13A113.36 (7)N1B—C2B—C13B112.51 (8)
C3A—C2A—N1A119.23 (8)C3B—C2B—N1B119.59 (8)
C3A—C2A—C13A127.37 (8)C3B—C2B—C13B127.86 (9)
C2A—C3A—C4A120.17 (7)C2B—C3B—C4B120.50 (8)
C2A—C3A—C14A119.84 (8)C2B—C3B—C14B119.94 (8)
C14A—C3A—C4A119.99 (7)C14B—C3B—C4B119.50 (8)
C3A—C4A—C17A111.17 (7)C3B—C4B—C17B112.57 (7)
C5A—C4A—C3A109.20 (7)C5B—C4B—C3B109.09 (7)
C5A—C4A—C17A112.05 (7)C5B—C4B—C17B111.19 (7)
C6A—C5A—C4A120.12 (7)C6B—C5B—C4B120.05 (7)
C10A—C5A—C4A120.36 (7)C10B—C5B—C4B121.01 (8)
C10A—C5A—C6A119.51 (7)C10B—C5B—C6B118.93 (8)
O1A—C6A—C5A120.93 (8)O1B—C6B—C5B122.00 (8)
O1A—C6A—C7A120.49 (8)O1B—C6B—C7B119.74 (8)
C5A—C6A—C7A118.54 (7)C5B—C6B—C7B118.21 (7)
C6A—C7A—C8A113.41 (7)C6B—C7B—C8B113.78 (7)
C9A—C8A—C7A108.72 (7)C7B—C8B—C9B108.25 (7)
C11A—C8A—C7A109.30 (7)C7B—C8B—C11B109.50 (7)
C11A—C8A—C9A111.15 (7)C9B—C8B—C11B110.73 (7)
C12A—C8A—C7A109.71 (7)C12B—C8B—C7B109.08 (7)
C12A—C8A—C9A109.08 (7)C12B—C8B—C9B109.31 (7)
C12A—C8A—C11A108.87 (7)C12B—C8B—C11B109.94 (8)
C10A—C9A—C8A113.17 (7)C10B—C9B—C8B113.28 (7)
N1A—C10A—C9A115.91 (7)N1B—C10B—C9B115.54 (7)
C5A—C10A—N1A119.81 (8)C5B—C10B—N1B119.61 (8)
C5A—C10A—C9A124.26 (7)C5B—C10B—C9B124.85 (8)
O2A—C14A—O3A121.80 (8)O2B—C14B—O3B121.11 (9)
O2A—C14A—C3A126.64 (8)O2B—C14B—C3B126.85 (9)
O3A—C14A—C3A111.55 (7)O3B—C14B—C3B112.03 (8)
O3A—C15A—C16A110.04 (8)O3B—C15B—C16B108.38 (8)
C18A—C17A—C4A120.65 (7)C18B—C17B—C4B119.57 (8)
C22A—C17A—C4A120.45 (8)C18B—C17B—C22B119.86 (8)
C22A—C17A—C18A118.83 (8)C22B—C17B—C4B120.56 (8)
C19A—C18A—C17A120.88 (8)C19B—C18B—C17B119.78 (8)
O5A—C19A—C18A125.29 (8)O5B—C19B—C18B125.90 (8)
O5A—C19A—C20A114.41 (8)O5B—C19B—C20B113.51 (8)
C18A—C19A—C20A120.30 (8)C18B—C19B—C20B120.59 (8)
O4A—C20A—C19A117.75 (8)O4B—C20B—C19B120.77 (8)
O4A—C20A—C21A123.89 (8)O4B—C20B—C21B119.34 (8)
C21A—C20A—C19A118.35 (8)C21B—C20B—C19B119.89 (8)
O6A—C21A—C20A118.27 (8)O6B—C21B—C20B114.60 (8)
O6A—C21A—C22A120.27 (8)O6B—C21B—C22B125.54 (8)
C20A—C21A—C22A121.37 (8)C20B—C21B—C22B119.85 (8)
C17A—C22A—C21A120.23 (8)C17B—C22B—C21B120.02 (8)
O1A—C6A—C7A—C8A151.01 (8)O1B—C6B—C7B—C8B147.46 (8)
O4A—C20A—C21A—O6A3.22 (13)O4B—C20B—C21B—O6B0.68 (12)
O4A—C20A—C21A—C22A179.97 (8)O4B—C20B—C21B—C22B179.08 (8)
O5A—C19A—C20A—O4A0.60 (12)O5B—C19B—C20B—O4B0.23 (12)
O5A—C19A—C20A—C21A178.29 (8)O5B—C19B—C20B—C21B179.96 (8)
O6A—C21A—C22A—C17A176.30 (8)O6B—C21B—C22B—C17B178.23 (8)
N1A—C2A—C3A—C4A8.37 (12)N1B—C2B—C3B—C4B5.35 (13)
N1A—C2A—C3A—C14A170.77 (8)N1B—C2B—C3B—C14B171.69 (8)
C2A—N1A—C10A—C5A16.97 (12)C2B—N1B—C10B—C5B17.81 (13)
C2A—N1A—C10A—C9A161.69 (8)C2B—N1B—C10B—C9B161.71 (8)
C2A—C3A—C4A—C5A29.30 (10)C2B—C3B—C4B—C5B26.83 (11)
C2A—C3A—C4A—C17A94.83 (9)C2B—C3B—C4B—C17B97.09 (10)
C2A—C3A—C14A—O2A2.27 (14)C2B—C3B—C14B—O2B3.16 (15)
C2A—C3A—C14A—O3A176.45 (8)C2B—C3B—C14B—O3B178.35 (8)
C3A—C4A—C5A—C6A149.71 (8)C3B—C4B—C5B—C6B153.27 (8)
C3A—C4A—C5A—C10A29.31 (10)C3B—C4B—C5B—C10B28.25 (11)
C3A—C4A—C17A—C18A83.76 (9)C3B—C4B—C17B—C18B84.89 (10)
C3A—C4A—C17A—C22A93.08 (9)C3B—C4B—C17B—C22B96.04 (9)
C4A—C3A—C14A—O2A178.59 (8)C4B—C3B—C14B—O2B173.92 (9)
C4A—C3A—C14A—O3A2.69 (11)C4B—C3B—C14B—O3B4.58 (11)
C4A—C5A—C6A—O1A1.72 (12)C4B—C5B—C6B—O1B0.45 (13)
C4A—C5A—C6A—C7A179.35 (7)C4B—C5B—C6B—C7B177.94 (7)
C4A—C5A—C10A—N1A8.32 (12)C4B—C5B—C10B—N1B7.91 (12)
C4A—C5A—C10A—C9A173.14 (7)C4B—C5B—C10B—C9B172.62 (8)
C4A—C17A—C18A—C19A176.22 (8)C4B—C17B—C18B—C19B178.18 (8)
C4A—C17A—C22A—C21A175.56 (8)C4B—C17B—C22B—C21B178.27 (8)
C5A—C4A—C17A—C18A38.74 (10)C5B—C4B—C17B—C18B37.86 (11)
C5A—C4A—C17A—C22A144.43 (8)C5B—C4B—C17B—C22B141.21 (8)
C5A—C6A—C7A—C8A31.35 (11)C5B—C6B—C7B—C8B34.99 (11)
C6A—C5A—C10A—N1A170.71 (8)C6B—C5B—C10B—N1B173.59 (8)
C6A—C5A—C10A—C9A7.84 (12)C6B—C5B—C10B—C9B5.88 (13)
C6A—C7A—C8A—C9A53.22 (9)C6B—C7B—C8B—C9B54.30 (10)
C6A—C7A—C8A—C11A68.27 (9)C6B—C7B—C8B—C11B66.51 (10)
C6A—C7A—C8A—C12A172.43 (7)C6B—C7B—C8B—C12B173.14 (8)
C7A—C8A—C9A—C10A45.78 (9)C7B—C8B—C9B—C10B44.60 (10)
C8A—C9A—C10A—N1A164.48 (7)C8B—C9B—C10B—N1B164.10 (8)
C8A—C9A—C10A—C5A16.93 (12)C8B—C9B—C10B—C5B16.41 (12)
C10A—N1A—C2A—C3A16.82 (12)C10B—N1B—C2B—C3B19.06 (13)
C10A—N1A—C2A—C13A161.19 (8)C10B—N1B—C2B—C13B158.87 (8)
C10A—C5A—C6A—O1A177.31 (8)C10B—C5B—C6B—O1B178.96 (9)
C10A—C5A—C6A—C7A0.32 (12)C10B—C5B—C6B—C7B3.55 (12)
C11A—C8A—C9A—C10A74.57 (9)C11B—C8B—C9B—C10B75.44 (9)
C12A—C8A—C9A—C10A165.38 (7)C12B—C8B—C9B—C10B163.30 (8)
C13A—C2A—C3A—C4A173.92 (8)C13B—C2B—C3B—C4B177.07 (9)
C13A—C2A—C3A—C14A6.94 (13)C13B—C2B—C3B—C14B5.89 (14)
C14A—O3A—C15A—C16A77.56 (10)C14B—O3B—C15B—C16B173.74 (8)
C14A—C3A—C4A—C5A149.84 (7)C14B—C3B—C4B—C5B150.23 (8)
C14A—C3A—C4A—C17A86.04 (9)C14B—C3B—C4B—C17B85.86 (10)
C15A—O3A—C14A—O2A8.56 (12)C15B—O3B—C14B—O2B3.78 (13)
C15A—O3A—C14A—C3A170.22 (7)C15B—O3B—C14B—C3B174.82 (8)
C17A—C4A—C5A—C6A86.68 (9)C17B—C4B—C5B—C6B82.01 (10)
C17A—C4A—C5A—C10A94.30 (9)C17B—C4B—C5B—C10B96.48 (9)
C17A—C18A—C19A—O5A179.24 (8)C17B—C18B—C19B—O5B179.14 (8)
C17A—C18A—C19A—C20A0.95 (13)C17B—C18B—C19B—C20B0.19 (13)
C18A—C17A—C22A—C21A1.33 (13)C18B—C17B—C22B—C21B0.80 (13)
C18A—C19A—C20A—O4A179.24 (8)C18B—C19B—C20B—O4B179.18 (8)
C18A—C19A—C20A—C21A1.87 (13)C18B—C19B—C20B—C21B0.63 (13)
C19A—C20A—C21A—O6A177.97 (8)C19B—C20B—C21B—O6B179.13 (8)
C19A—C20A—C21A—C22A1.22 (13)C19B—C20B—C21B—C22B0.72 (13)
C20A—C21A—C22A—C17A0.39 (13)C20B—C21B—C22B—C17B0.02 (13)
C22A—C17A—C18A—C19A0.67 (13)C22B—C17B—C18B—C19B0.89 (13)
C23A—O5A—C19A—C18A0.11 (14)C23B—O5B—C19B—C18B8.86 (14)
C23A—O5A—C19A—C20A179.94 (8)C23B—O5B—C19B—C20B171.77 (9)
C24A—O6A—C21A—C20A93.57 (10)C24B—O6B—C21B—C20B171.90 (8)
C24A—O6A—C21A—C22A89.64 (10)C24B—O6B—C21B—C22B9.80 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4A—H4C···O1Ai0.848 (17)1.937 (17)2.6948 (9)148.0 (16)
N1A—H1A···O1Bii0.880 (15)1.890 (15)2.7666 (10)174.1 (13)
C7A—H7C···O6Bii0.992.673.4510 (12)136
C12A—H12D···O2Aiii0.982.603.5237 (12)157
C13A—H13D···O1Bii0.982.593.3590 (12)136
C16A—H16D···O4Aiv0.982.653.3136 (13)126
C24A—H24E···O4Bv0.982.433.3105 (13)149
N1B—H1···O1Ai0.888 (15)2.166 (15)2.9479 (10)146.6 (12)
C7B—H7B···O2A0.992.693.4992 (11)139
C9B—H9B···O6A0.992.593.5751 (11)172
C15B—H15A···O5Biii0.992.603.4993 (12)151
C23B—H23B···O2Bvi0.982.553.4277 (13)149
Symmetry codes: (i) x+1/2, y+3/2, z+1/2; (ii) x+1, y+1, z+1; (iii) x1, y, z; (iv) x+1/2, y+3/2, z1/2; (v) x+3/2, y+1/2, z+3/2; (vi) x+1, y, z.
Ethyl 4-(anthracen-9-yl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate (III) top
Crystal data top
C29H29NO3F(000) = 936
Mr = 439.53Dx = 1.229 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 11.6527 (3) ÅCell parameters from 9872 reflections
b = 18.1986 (4) Åθ = 2.2–27.6°
c = 12.3435 (3) ŵ = 0.08 mm1
β = 114.8758 (12)°T = 100 K
V = 2374.74 (10) Å3Prism, yellow
Z = 40.45 × 0.12 × 0.11 mm
Data collection top
Bruker SMART BREEZE CCD
diffractometer
Rint = 0.055
φ and ω scansθmax = 28.3°, θmin = 2.1°
72579 measured reflectionsh = 1515
5902 independent reflectionsk = 2424
4515 reflections with I > 2σ(I)l = 1616
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.135 w = 1/[σ2(Fo2) + (0.067P)2 + 1.0544P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
5902 reflectionsΔρmax = 0.54 e Å3
306 parametersΔρmin = 0.22 e Å3
0 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*/Ueq
O10.34009 (10)0.80683 (6)0.16928 (9)0.0235 (2)
O20.31457 (11)0.54998 (7)0.51900 (11)0.0331 (3)
O30.19449 (10)0.64051 (6)0.40339 (10)0.0256 (2)
N10.61943 (12)0.65569 (7)0.47273 (11)0.0182 (3)
H10.6990 (19)0.6551 (11)0.5295 (18)0.032 (5)*
C20.52536 (13)0.62310 (7)0.49757 (12)0.0177 (3)
C30.40249 (13)0.63374 (7)0.42341 (12)0.0169 (3)
C40.36056 (13)0.68248 (7)0.31263 (12)0.0153 (3)
H40.3047110.7211530.3224530.018*
C50.47314 (13)0.72274 (7)0.30848 (12)0.0152 (3)
C60.44911 (13)0.78495 (7)0.22944 (12)0.0170 (3)
C70.55990 (14)0.82620 (8)0.22492 (13)0.0202 (3)
H7A0.5752710.8708310.2749400.024*
H7B0.5363010.8424250.1417100.024*
C80.68311 (14)0.78268 (8)0.26676 (13)0.0199 (3)
C90.70717 (13)0.74830 (8)0.38790 (13)0.0188 (3)
H9A0.7789560.7135670.4109030.023*
H9B0.7314710.7875290.4490800.023*
C100.59379 (13)0.70822 (7)0.38663 (12)0.0158 (3)
C110.67348 (15)0.72310 (9)0.17535 (14)0.0260 (3)
H11A0.6028600.6901430.1641690.039*
H11B0.7523760.6948700.2044890.039*
H11C0.6590390.7462430.0989980.039*
C120.79290 (15)0.83464 (9)0.28370 (15)0.0262 (3)
H12A0.8723970.8069420.3147650.039*
H12B0.7974300.8734610.3403910.039*
H12C0.7790710.8567450.2067890.039*
C130.57721 (15)0.58079 (8)0.61266 (13)0.0240 (3)
H13A0.6631010.5978540.6628730.036*
H13B0.5793140.5283290.5956500.036*
H13C0.5230730.5885570.6545820.036*
C140.30380 (14)0.60270 (8)0.45520 (13)0.0215 (3)
C150.08506 (16)0.61002 (11)0.41441 (16)0.0340 (4)
H15A0.0232160.6497030.4041720.041*
H15B0.1113720.5891430.4954090.041*
C160.0228 (2)0.55080 (12)0.32261 (18)0.0466 (5)
H16A0.0807150.5090480.3380880.070*
H16B0.0024290.5703540.2426270.070*
H16C0.0550150.5345730.3275450.070*
C170.27883 (12)0.64059 (7)0.19723 (12)0.0149 (3)
C180.33088 (13)0.58220 (7)0.15614 (12)0.0151 (3)
C190.46066 (13)0.55974 (8)0.21467 (12)0.0171 (3)
H190.5159950.5855010.2839150.021*
C200.50692 (14)0.50254 (8)0.17387 (13)0.0199 (3)
H200.5934320.4892060.2150310.024*
C210.42774 (15)0.46271 (8)0.07091 (14)0.0223 (3)
H210.4609220.4227980.0434320.027*
C220.30435 (14)0.48181 (8)0.01176 (13)0.0206 (3)
H220.2518520.4552280.0577340.025*
C230.25166 (13)0.54115 (8)0.05188 (12)0.0174 (3)
C240.12363 (14)0.55804 (8)0.00657 (12)0.0192 (3)
H240.0716270.5302690.0748030.023*
C250.06980 (13)0.61454 (8)0.03234 (12)0.0178 (3)
C260.14856 (13)0.65780 (7)0.13450 (12)0.0162 (3)
C270.08637 (13)0.71596 (8)0.16756 (13)0.0191 (3)
H270.1353060.7476910.2314720.023*
C280.04097 (14)0.72696 (8)0.10984 (14)0.0220 (3)
H280.0788740.7654620.1353650.026*
C290.11792 (14)0.68199 (8)0.01238 (14)0.0228 (3)
H290.2068310.6893770.0254950.027*
C300.06317 (14)0.62827 (8)0.02621 (13)0.0210 (3)
H300.1141570.5993100.0932930.025*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0196 (5)0.0252 (5)0.0203 (5)0.0012 (4)0.0030 (4)0.0046 (4)
O20.0326 (7)0.0324 (6)0.0380 (7)0.0054 (5)0.0184 (6)0.0102 (5)
O30.0203 (5)0.0324 (6)0.0278 (6)0.0043 (4)0.0139 (5)0.0013 (5)
N10.0150 (6)0.0202 (6)0.0164 (6)0.0014 (5)0.0038 (5)0.0016 (5)
C20.0210 (7)0.0160 (6)0.0158 (6)0.0025 (5)0.0074 (6)0.0012 (5)
C30.0198 (7)0.0171 (6)0.0147 (6)0.0025 (5)0.0082 (5)0.0011 (5)
C40.0146 (6)0.0163 (6)0.0147 (6)0.0009 (5)0.0059 (5)0.0005 (5)
C50.0156 (6)0.0164 (6)0.0140 (6)0.0020 (5)0.0065 (5)0.0020 (5)
C60.0187 (7)0.0178 (6)0.0135 (6)0.0011 (5)0.0058 (5)0.0016 (5)
C70.0231 (7)0.0202 (7)0.0173 (7)0.0036 (6)0.0084 (6)0.0021 (5)
C80.0196 (7)0.0222 (7)0.0195 (7)0.0046 (6)0.0099 (6)0.0007 (5)
C90.0146 (7)0.0228 (7)0.0179 (7)0.0016 (5)0.0058 (5)0.0004 (5)
C100.0169 (7)0.0162 (6)0.0146 (6)0.0012 (5)0.0070 (5)0.0014 (5)
C110.0274 (8)0.0308 (8)0.0247 (8)0.0053 (6)0.0156 (7)0.0049 (6)
C120.0241 (8)0.0297 (8)0.0277 (8)0.0080 (6)0.0137 (7)0.0003 (6)
C130.0268 (8)0.0236 (7)0.0180 (7)0.0033 (6)0.0061 (6)0.0033 (6)
C140.0225 (7)0.0266 (7)0.0166 (7)0.0058 (6)0.0092 (6)0.0055 (6)
C150.0261 (8)0.0496 (11)0.0316 (9)0.0113 (8)0.0174 (7)0.0048 (8)
C160.0397 (11)0.0598 (13)0.0417 (11)0.0258 (10)0.0186 (9)0.0104 (10)
C170.0157 (6)0.0156 (6)0.0140 (6)0.0022 (5)0.0067 (5)0.0004 (5)
C180.0168 (6)0.0162 (6)0.0141 (6)0.0022 (5)0.0083 (5)0.0013 (5)
C190.0172 (7)0.0182 (6)0.0164 (7)0.0014 (5)0.0076 (5)0.0013 (5)
C200.0200 (7)0.0205 (7)0.0220 (7)0.0022 (5)0.0115 (6)0.0026 (5)
C210.0301 (8)0.0174 (7)0.0253 (8)0.0001 (6)0.0175 (7)0.0008 (6)
C220.0260 (8)0.0188 (7)0.0199 (7)0.0070 (6)0.0125 (6)0.0046 (5)
C230.0207 (7)0.0170 (6)0.0162 (7)0.0041 (5)0.0094 (6)0.0005 (5)
C240.0207 (7)0.0198 (7)0.0152 (6)0.0056 (5)0.0057 (6)0.0006 (5)
C250.0166 (7)0.0189 (7)0.0169 (7)0.0043 (5)0.0062 (5)0.0029 (5)
C260.0154 (6)0.0170 (6)0.0168 (6)0.0027 (5)0.0074 (5)0.0023 (5)
C270.0176 (7)0.0195 (7)0.0209 (7)0.0006 (5)0.0087 (6)0.0014 (5)
C280.0193 (7)0.0220 (7)0.0275 (8)0.0017 (6)0.0125 (6)0.0055 (6)
C290.0144 (7)0.0262 (7)0.0260 (8)0.0014 (6)0.0067 (6)0.0094 (6)
C300.0175 (7)0.0230 (7)0.0193 (7)0.0060 (5)0.0046 (6)0.0041 (6)
Geometric parameters (Å, º) top
O1—C61.2370 (17)C9—C101.5036 (19)
O2—C141.2138 (19)C15—C161.510 (3)
O3—C141.3489 (19)C17—C181.4188 (19)
O3—C151.4486 (19)C17—C261.4188 (19)
N1—C21.3893 (18)C18—C191.4342 (19)
N1—C101.3658 (18)C18—C231.4377 (19)
C2—C31.350 (2)C19—C201.362 (2)
C2—C131.5013 (19)C20—C211.416 (2)
C3—C41.5275 (18)C21—C221.356 (2)
C3—C141.4749 (19)C22—C231.430 (2)
C4—C51.5220 (18)C23—C241.391 (2)
C4—C171.5413 (18)C24—C251.391 (2)
C5—C61.4430 (19)C25—C261.4417 (19)
C5—C101.3550 (19)C25—C301.430 (2)
C6—C71.5146 (19)C26—C271.4356 (19)
C7—C81.527 (2)C27—C281.364 (2)
C8—C91.534 (2)C28—C291.419 (2)
C8—C111.534 (2)C29—C301.358 (2)
C8—C121.533 (2)
C14—O3—C15116.95 (13)O2—C14—O3122.01 (14)
C10—N1—C2122.41 (12)O2—C14—C3126.59 (14)
N1—C2—C13112.76 (12)O3—C14—C3111.41 (12)
C3—C2—N1119.95 (12)O3—C15—C16111.51 (14)
C3—C2—C13127.23 (13)C18—C17—C4120.66 (12)
C2—C3—C4122.61 (12)C18—C17—C26119.36 (12)
C2—C3—C14119.20 (13)C26—C17—C4119.90 (12)
C14—C3—C4117.97 (12)C17—C18—C19123.51 (12)
C3—C4—C17112.38 (11)C17—C18—C23119.94 (12)
C5—C4—C3110.73 (11)C19—C18—C23116.53 (12)
C5—C4—C17114.41 (11)C20—C19—C18121.93 (13)
C6—C5—C4118.40 (12)C19—C20—C21120.87 (14)
C10—C5—C4122.21 (12)C22—C21—C20119.68 (13)
C10—C5—C6118.85 (12)C21—C22—C23121.31 (13)
O1—C6—C5121.10 (13)C22—C23—C18119.67 (13)
O1—C6—C7119.63 (12)C24—C23—C18119.61 (13)
C5—C6—C7119.20 (12)C24—C23—C22120.69 (13)
C6—C7—C8115.17 (12)C25—C24—C23121.68 (13)
C7—C8—C9107.55 (11)C24—C25—C26119.48 (13)
C7—C8—C11110.50 (12)C24—C25—C30120.32 (13)
C7—C8—C12109.77 (12)C30—C25—C26120.17 (13)
C9—C8—C11110.82 (12)C17—C26—C25119.88 (12)
C12—C8—C9108.59 (12)C17—C26—C27124.04 (13)
C12—C8—C11109.57 (12)C27—C26—C25116.07 (12)
C10—C9—C8112.84 (11)C28—C27—C26121.87 (14)
N1—C10—C9115.33 (12)C27—C28—C29121.26 (14)
C5—C10—N1120.82 (12)C30—C29—C28119.33 (13)
C5—C10—C9123.84 (12)C29—C30—C25121.17 (14)
O1—C6—C7—C8160.55 (13)C13—C2—C3—C4175.60 (13)
N1—C2—C3—C41.6 (2)C13—C2—C3—C141.1 (2)
N1—C2—C3—C14176.08 (12)C14—O3—C15—C1682.03 (19)
C2—N1—C10—C510.5 (2)C14—C3—C4—C5167.62 (12)
C2—N1—C10—C9168.21 (12)C14—C3—C4—C1763.06 (16)
C2—C3—C4—C56.93 (18)C15—O3—C14—O27.7 (2)
C2—C3—C4—C17122.39 (14)C15—O3—C14—C3172.08 (12)
C2—C3—C14—O225.1 (2)C17—C4—C5—C667.85 (16)
C2—C3—C14—O3155.09 (13)C17—C4—C5—C10120.75 (14)
C3—C4—C5—C6163.92 (11)C17—C18—C19—C20178.82 (13)
C3—C4—C5—C107.48 (18)C17—C18—C23—C22179.25 (12)
C3—C4—C17—C1865.27 (16)C17—C18—C23—C241.38 (19)
C3—C4—C17—C26111.42 (14)C17—C26—C27—C28175.04 (13)
C4—C3—C14—O2160.16 (14)C18—C17—C26—C251.94 (19)
C4—C3—C14—O319.65 (17)C18—C17—C26—C27179.50 (12)
C4—C5—C6—O12.40 (19)C18—C19—C20—C210.1 (2)
C4—C5—C6—C7179.41 (12)C18—C23—C24—C250.8 (2)
C4—C5—C10—N10.6 (2)C19—C18—C23—C220.43 (18)
C4—C5—C10—C9178.06 (12)C19—C18—C23—C24177.45 (12)
C4—C17—C18—C192.05 (19)C19—C20—C21—C220.2 (2)
C4—C17—C18—C23176.69 (12)C20—C21—C22—C230.6 (2)
C4—C17—C26—C25174.79 (12)C21—C22—C23—C180.8 (2)
C4—C17—C26—C273.8 (2)C21—C22—C23—C24177.10 (13)
C5—C4—C17—C1862.12 (16)C22—C23—C24—C25178.66 (13)
C5—C4—C17—C26121.19 (13)C23—C18—C19—C200.04 (19)
C5—C6—C7—C822.39 (18)C23—C24—C25—C261.1 (2)
C6—C5—C10—N1171.93 (12)C23—C24—C25—C30177.01 (13)
C6—C5—C10—C96.7 (2)C24—C25—C26—C172.52 (19)
C6—C7—C8—C949.79 (16)C24—C25—C26—C27178.81 (12)
C6—C7—C8—C1171.30 (15)C24—C25—C30—C29178.32 (13)
C6—C7—C8—C12167.75 (12)C25—C26—C27—C283.6 (2)
C7—C8—C9—C1049.90 (15)C26—C17—C18—C19178.75 (12)
C8—C9—C10—N1157.27 (12)C26—C17—C18—C230.01 (19)
C8—C9—C10—C524.03 (19)C26—C25—C30—C290.2 (2)
C10—N1—C2—C311.0 (2)C26—C27—C28—C291.2 (2)
C10—N1—C2—C13166.55 (13)C27—C28—C29—C301.8 (2)
C10—C5—C6—O1169.29 (13)C28—C29—C30—C252.3 (2)
C10—C5—C6—C77.72 (19)C30—C25—C26—C17175.63 (12)
C11—C8—C9—C1070.98 (15)C30—C25—C26—C273.04 (19)
C12—C8—C9—C10168.62 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.90 (2)1.94 (2)2.7776 (16)154.2 (18)
C13—H13B···O2ii0.982.653.409 (2)134
C19—H19···N10.952.483.4148 (19)168
Symmetry codes: (i) x+1/2, y+3/2, z+1/2; (ii) x+1, y+1, z+1.
 

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