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
CCDC references: 1973149; 1973148; 1973147
Key indicators
Structure: I
- Single-crystal X-ray study
- T = 100 K
- Mean (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 (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 (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
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
C23H27NO6 | Z = 2 |
Mr = 413.45 | F(000) = 440 |
Triclinic, P1 | Dx = 1.297 Mg m−3 |
a = 8.7024 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.8709 (4) Å | Cell parameters from 9400 reflections |
c = 13.1621 (5) Å | θ = 2.5–28.8° |
α = 90.3822 (19)° | µ = 0.09 mm−1 |
β = 108.9608 (18)° | T = 100 K |
γ = 97.3571 (18)° | Prism, yellow |
V = 1059.08 (7) Å3 | 0.39 × 0.25 × 0.13 mm |
Data collection top
Bruker SMART BREEZE CCD diffractometer | Rint = 0.031 |
φ and ω scans | θmax = 29.1°, θmin = 2.5° |
29458 measured reflections | h = −11→11 |
5315 independent reflections | k = −13→13 |
4254 reflections with I > 2σ(I) | l = −17→17 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.054 | H 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 reflections | Δρmax = 0.65 e Å−3 |
291 parameters | Δρmin = −0.25 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O5 | 0.04549 (13) | 0.40295 (11) | 0.15867 (9) | 0.0208 (2) | |
O3 | 0.21250 (13) | 0.20362 (12) | 0.17985 (9) | 0.0236 (3) | |
O4 | 0.68127 (15) | 0.53646 (13) | 0.29954 (11) | 0.0320 (3) | |
O6 | 0.50510 (15) | 0.73583 (13) | 0.29901 (10) | 0.0296 (3) | |
C9 | 0.11023 (18) | 0.52479 (16) | 0.18099 (11) | 0.0185 (3) | |
O2 | 0.61739 (15) | 0.30380 (15) | 0.47643 (10) | 0.0346 (3) | |
O1 | 0.50744 (18) | 0.09861 (14) | 0.41032 (11) | 0.0380 (3) | |
C16 | 0.44538 (19) | 0.37141 (16) | 0.25549 (12) | 0.0203 (3) | |
C8 | 0.27365 (18) | 0.56290 (16) | 0.25447 (11) | 0.0183 (3) | |
C7 | 0.37049 (18) | 0.45661 (15) | 0.31983 (11) | 0.0182 (3) | |
H7 | 0.466554 | 0.510901 | 0.375098 | 0.022* | |
N1 | 0.49857 (19) | 0.21541 (16) | 0.43905 (11) | 0.0279 (3) | |
C10 | 0.0114 (2) | 0.63357 (17) | 0.12509 (13) | 0.0235 (3) | |
H10A | −0.104225 | 0.606543 | 0.120725 | 0.028* | |
H10B | 0.014314 | 0.636767 | 0.050574 | 0.028* | |
C17 | 0.36806 (18) | 0.25256 (16) | 0.19662 (12) | 0.0209 (3) | |
C13 | 0.34611 (19) | 0.69472 (17) | 0.25407 (12) | 0.0218 (3) | |
C6 | 0.28101 (18) | 0.36902 (16) | 0.38462 (11) | 0.0191 (3) | |
C21 | 0.61154 (19) | 0.42118 (18) | 0.26078 (13) | 0.0237 (3) | |
C18 | 0.4540 (2) | 0.15999 (18) | 0.14946 (14) | 0.0249 (3) | |
C12 | 0.2536 (2) | 0.80723 (17) | 0.20066 (13) | 0.0249 (3) | |
H12A | 0.273724 | 0.823572 | 0.131642 | 0.030* | |
H12B | 0.296854 | 0.892238 | 0.246928 | 0.030* | |
C11 | 0.0687 (2) | 0.77713 (16) | 0.17870 (13) | 0.0230 (3) | |
C1 | 0.3365 (2) | 0.25007 (17) | 0.43280 (12) | 0.0238 (3) | |
C2 | 0.2498 (2) | 0.16111 (18) | 0.48286 (13) | 0.0285 (4) | |
H2 | 0.288304 | 0.078128 | 0.509312 | 0.034* | |
C4 | 0.0550 (2) | 0.31725 (19) | 0.45528 (13) | 0.0277 (4) | |
H4 | −0.039275 | 0.344284 | 0.466757 | 0.033* | |
C19 | 0.6040 (2) | 0.23166 (18) | 0.12570 (14) | 0.0267 (4) | |
C14 | 0.0311 (2) | 0.78794 (18) | 0.28423 (14) | 0.0280 (4) | |
H14A | −0.086246 | 0.759417 | 0.270562 | 0.042* | |
H14B | 0.060734 | 0.882821 | 0.313448 | 0.042* | |
H14C | 0.094698 | 0.728498 | 0.336144 | 0.042* | |
C5 | 0.13841 (19) | 0.40093 (17) | 0.40030 (12) | 0.0220 (3) | |
H5 | 0.097129 | 0.482417 | 0.372502 | 0.026* | |
C20 | 0.7057 (2) | 0.3260 (2) | 0.22307 (15) | 0.0310 (4) | |
H20A | 0.756393 | 0.268957 | 0.283196 | 0.037* | |
H20B | 0.795669 | 0.381263 | 0.205032 | 0.037* | |
C3 | 0.1069 (2) | 0.19581 (19) | 0.49334 (14) | 0.0304 (4) | |
H3A | 0.044832 | 0.136339 | 0.526547 | 0.036* | |
C22 | 0.7073 (2) | 0.1264 (2) | 0.10677 (18) | 0.0361 (4) | |
H22A | 0.740886 | 0.071941 | 0.170262 | 0.054* | |
H22B | 0.804872 | 0.173597 | 0.093904 | 0.054* | |
H22C | 0.642313 | 0.066101 | 0.043989 | 0.054* | |
C15 | −0.0190 (2) | 0.87981 (19) | 0.10242 (15) | 0.0321 (4) | |
H15A | 0.001219 | 0.871620 | 0.033763 | 0.048* | |
H15B | 0.022549 | 0.972726 | 0.134428 | 0.048* | |
H15C | −0.137191 | 0.860984 | 0.090111 | 0.048* | |
C23 | 0.5504 (3) | 0.3151 (2) | 0.02618 (16) | 0.0377 (4) | |
H23A | 0.491440 | 0.253400 | −0.036919 | 0.057* | |
H23B | 0.647292 | 0.366841 | 0.015346 | 0.057* | |
H23C | 0.478164 | 0.378662 | 0.036190 | 0.057* | |
H3 | 0.160 (4) | 0.282 (3) | 0.187 (2) | 0.069 (9)* | |
H18A | 0.377 (3) | 0.114 (2) | 0.093 (2) | 0.042 (6)* | |
H18B | 0.486 (3) | 0.084 (2) | 0.2037 (19) | 0.042 (6)* | |
H6 | 0.569 (5) | 0.647 (4) | 0.307 (3) | 0.103 (12)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O5 | 0.0178 (5) | 0.0222 (6) | 0.0217 (5) | 0.0004 (4) | 0.0066 (4) | −0.0023 (4) |
O3 | 0.0172 (5) | 0.0246 (6) | 0.0287 (6) | −0.0011 (4) | 0.0089 (4) | −0.0045 (5) |
O4 | 0.0232 (6) | 0.0310 (7) | 0.0418 (7) | −0.0051 (5) | 0.0142 (5) | −0.0105 (5) |
O6 | 0.0217 (6) | 0.0284 (6) | 0.0351 (7) | −0.0051 (5) | 0.0080 (5) | −0.0042 (5) |
C9 | 0.0194 (7) | 0.0225 (7) | 0.0163 (7) | 0.0031 (6) | 0.0095 (6) | −0.0003 (5) |
O2 | 0.0232 (6) | 0.0471 (8) | 0.0292 (6) | 0.0049 (6) | 0.0029 (5) | 0.0016 (6) |
O1 | 0.0496 (8) | 0.0338 (7) | 0.0369 (7) | 0.0206 (6) | 0.0170 (6) | 0.0081 (6) |
C16 | 0.0182 (7) | 0.0224 (7) | 0.0216 (7) | 0.0027 (6) | 0.0083 (6) | −0.0001 (6) |
C8 | 0.0177 (7) | 0.0213 (7) | 0.0167 (6) | 0.0027 (5) | 0.0068 (5) | −0.0018 (5) |
C7 | 0.0163 (7) | 0.0209 (7) | 0.0172 (7) | 0.0005 (5) | 0.0061 (5) | −0.0027 (5) |
N1 | 0.0304 (8) | 0.0335 (8) | 0.0209 (7) | 0.0114 (6) | 0.0070 (6) | 0.0047 (6) |
C10 | 0.0233 (8) | 0.0249 (8) | 0.0202 (7) | 0.0034 (6) | 0.0043 (6) | 0.0017 (6) |
C17 | 0.0178 (7) | 0.0246 (8) | 0.0211 (7) | 0.0024 (6) | 0.0075 (6) | 0.0004 (6) |
C13 | 0.0210 (7) | 0.0249 (8) | 0.0203 (7) | −0.0007 (6) | 0.0095 (6) | −0.0032 (6) |
C6 | 0.0185 (7) | 0.0236 (7) | 0.0143 (6) | 0.0000 (6) | 0.0054 (5) | −0.0029 (5) |
C21 | 0.0181 (7) | 0.0310 (9) | 0.0213 (7) | 0.0006 (6) | 0.0068 (6) | −0.0029 (6) |
C18 | 0.0211 (8) | 0.0265 (8) | 0.0280 (8) | 0.0008 (6) | 0.0103 (7) | −0.0065 (7) |
C12 | 0.0299 (8) | 0.0208 (8) | 0.0260 (8) | −0.0003 (6) | 0.0135 (7) | 0.0017 (6) |
C11 | 0.0278 (8) | 0.0218 (8) | 0.0210 (7) | 0.0052 (6) | 0.0095 (6) | 0.0034 (6) |
C1 | 0.0234 (8) | 0.0280 (8) | 0.0186 (7) | 0.0048 (6) | 0.0044 (6) | −0.0028 (6) |
C2 | 0.0382 (10) | 0.0257 (8) | 0.0194 (7) | 0.0022 (7) | 0.0072 (7) | 0.0019 (6) |
C4 | 0.0255 (8) | 0.0383 (10) | 0.0210 (7) | 0.0000 (7) | 0.0115 (6) | −0.0012 (7) |
C19 | 0.0241 (8) | 0.0288 (9) | 0.0311 (8) | 0.0032 (6) | 0.0144 (7) | −0.0028 (7) |
C14 | 0.0333 (9) | 0.0289 (9) | 0.0278 (8) | 0.0079 (7) | 0.0166 (7) | 0.0018 (7) |
C5 | 0.0224 (8) | 0.0264 (8) | 0.0179 (7) | 0.0037 (6) | 0.0076 (6) | 0.0005 (6) |
C20 | 0.0176 (7) | 0.0369 (10) | 0.0395 (10) | −0.0011 (7) | 0.0128 (7) | −0.0102 (8) |
C3 | 0.0365 (9) | 0.0335 (9) | 0.0222 (8) | −0.0030 (7) | 0.0142 (7) | 0.0013 (7) |
C22 | 0.0283 (9) | 0.0356 (10) | 0.0493 (11) | 0.0062 (7) | 0.0190 (8) | −0.0077 (8) |
C15 | 0.0384 (10) | 0.0259 (9) | 0.0312 (9) | 0.0091 (7) | 0.0084 (8) | 0.0071 (7) |
C23 | 0.0470 (11) | 0.0377 (11) | 0.0379 (10) | 0.0098 (9) | 0.0254 (9) | 0.0049 (8) |
Geometric parameters (Å, º) top
O5—C9 | 1.2507 (19) | C17—C18 | 1.499 (2) |
O3—C17 | 1.3234 (19) | C13—C12 | 1.499 (2) |
O4—C21 | 1.240 (2) | C6—C1 | 1.404 (2) |
O6—C13 | 1.3228 (19) | C6—C5 | 1.395 (2) |
C9—C8 | 1.437 (2) | C21—C20 | 1.502 (2) |
C9—C10 | 1.507 (2) | C18—C19 | 1.528 (2) |
O2—N1 | 1.227 (2) | C12—C11 | 1.528 (2) |
O1—N1 | 1.231 (2) | C11—C14 | 1.533 (2) |
C16—C7 | 1.529 (2) | C11—C15 | 1.527 (2) |
C16—C17 | 1.370 (2) | C1—C2 | 1.391 (2) |
C16—C21 | 1.445 (2) | C2—C3 | 1.380 (3) |
C8—C7 | 1.523 (2) | C4—C5 | 1.389 (2) |
C8—C13 | 1.372 (2) | C4—C3 | 1.375 (3) |
C7—C6 | 1.533 (2) | C19—C20 | 1.526 (2) |
N1—C1 | 1.470 (2) | C19—C22 | 1.526 (2) |
C10—C11 | 1.527 (2) | C19—C23 | 1.526 (3) |
| | | |
O5—C9—C8 | 122.69 (14) | O4—C21—C16 | 122.67 (15) |
O5—C9—C10 | 117.37 (13) | O4—C21—C20 | 118.99 (14) |
C8—C9—C10 | 119.93 (13) | C16—C21—C20 | 118.26 (15) |
C17—C16—C7 | 124.87 (14) | C17—C18—C19 | 114.49 (14) |
C17—C16—C21 | 119.05 (14) | C13—C12—C11 | 113.81 (13) |
C21—C16—C7 | 116.07 (13) | C10—C11—C12 | 107.37 (13) |
C9—C8—C7 | 121.06 (13) | C10—C11—C14 | 111.47 (14) |
C13—C8—C9 | 117.49 (14) | C10—C11—C15 | 109.11 (14) |
C13—C8—C7 | 121.00 (13) | C12—C11—C14 | 110.01 (14) |
C16—C7—C6 | 112.82 (12) | C15—C11—C12 | 110.07 (14) |
C8—C7—C16 | 113.54 (12) | C15—C11—C14 | 108.80 (14) |
C8—C7—C6 | 114.51 (12) | C6—C1—N1 | 121.11 (15) |
O2—N1—O1 | 124.15 (16) | C2—C1—N1 | 114.97 (15) |
O2—N1—C1 | 117.60 (14) | C2—C1—C6 | 123.83 (15) |
O1—N1—C1 | 118.19 (15) | C3—C2—C1 | 118.67 (16) |
C9—C10—C11 | 115.19 (13) | C3—C4—C5 | 120.92 (16) |
O3—C17—C16 | 123.87 (14) | C20—C19—C18 | 107.98 (14) |
O3—C17—C18 | 112.79 (14) | C20—C19—C22 | 109.38 (15) |
C16—C17—C18 | 123.25 (14) | C22—C19—C18 | 110.18 (15) |
O6—C13—C8 | 123.82 (15) | C23—C19—C18 | 110.18 (15) |
O6—C13—C12 | 112.72 (14) | C23—C19—C20 | 109.85 (16) |
C8—C13—C12 | 123.46 (14) | C23—C19—C22 | 109.26 (15) |
C1—C6—C7 | 122.42 (13) | C4—C5—C6 | 122.05 (15) |
C5—C6—C7 | 122.82 (14) | C21—C20—C19 | 114.88 (14) |
C5—C6—C1 | 114.76 (14) | C4—C3—C2 | 119.41 (16) |
| | | |
O5—C9—C8—C7 | −7.3 (2) | C7—C6—C1—C2 | −173.36 (14) |
O5—C9—C8—C13 | 165.07 (14) | C7—C6—C5—C4 | 177.16 (14) |
O5—C9—C10—C11 | 161.40 (13) | N1—C1—C2—C3 | 171.47 (15) |
O3—C17—C18—C19 | 156.51 (14) | C10—C9—C8—C7 | 174.32 (13) |
O4—C21—C20—C19 | −146.42 (16) | C10—C9—C8—C13 | −13.3 (2) |
O6—C13—C12—C11 | −162.31 (13) | C17—C16—C7—C8 | −88.49 (18) |
C9—C8—C7—C16 | 78.45 (17) | C17—C16—C7—C6 | 43.9 (2) |
C9—C8—C7—C6 | −53.11 (18) | C17—C16—C21—O4 | 169.75 (16) |
C9—C8—C13—O6 | −164.77 (14) | C17—C16—C21—C20 | −13.6 (2) |
C9—C8—C13—C12 | 14.0 (2) | C17—C18—C19—C20 | 45.7 (2) |
C9—C10—C11—C12 | 49.40 (17) | C17—C18—C19—C22 | 165.08 (15) |
C9—C10—C11—C14 | −71.15 (18) | C17—C18—C19—C23 | −74.29 (19) |
C9—C10—C11—C15 | 168.67 (14) | C13—C8—C7—C16 | −93.69 (17) |
O2—N1—C1—C6 | 51.4 (2) | C13—C8—C7—C6 | 134.75 (14) |
O2—N1—C1—C2 | −125.14 (16) | C13—C12—C11—C10 | −48.40 (17) |
O1—N1—C1—C6 | −131.16 (16) | C13—C12—C11—C14 | 73.07 (17) |
O1—N1—C1—C2 | 52.2 (2) | C13—C12—C11—C15 | −167.05 (14) |
C16—C7—C6—C1 | 35.67 (19) | C6—C1—C2—C3 | −5.0 (2) |
C16—C7—C6—C5 | −144.27 (14) | C21—C16—C7—C8 | 92.93 (16) |
C16—C17—C18—C19 | −26.7 (2) | C21—C16—C7—C6 | −134.69 (14) |
C16—C21—C20—C19 | 36.8 (2) | C21—C16—C17—O3 | −174.70 (14) |
C8—C9—C10—C11 | −20.2 (2) | C21—C16—C17—C18 | 8.9 (2) |
C8—C7—C6—C1 | 167.58 (13) | C18—C19—C20—C21 | −51.4 (2) |
C8—C7—C6—C5 | −12.4 (2) | C1—C6—C5—C4 | −2.8 (2) |
C8—C13—C12—C11 | 18.8 (2) | C1—C2—C3—C4 | −0.7 (2) |
C7—C16—C17—O3 | 6.8 (3) | C5—C6—C1—N1 | −169.69 (14) |
C7—C16—C17—C18 | −169.69 (15) | C5—C6—C1—C2 | 6.6 (2) |
C7—C16—C21—O4 | −11.6 (2) | C5—C4—C3—C2 | 4.3 (3) |
C7—C16—C21—C20 | 165.04 (15) | C3—C4—C5—C6 | −2.5 (2) |
C7—C8—C13—O6 | 7.6 (2) | C22—C19—C20—C21 | −171.31 (16) |
C7—C8—C13—C12 | −173.56 (14) | C23—C19—C20—C21 | 68.8 (2) |
C7—C6—C1—N1 | 10.4 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O5 | 0.97 (3) | 1.62 (3) | 2.5570 (16) | 162 (3) |
O6—H6···O4 | 1.08 (4) | 1.58 (4) | 2.6437 (19) | 166 (3) |
C2—H2···O1i | 0.95 | 2.63 | 3.538 (2) | 160 |
C10—H10B···O5ii | 0.99 | 2.65 | 3.6138 (19) | 165 |
C15—H15B···O3iii | 0.98 | 2.58 | 3.505 (2) | 157 |
C18—H18B···O1 | 1.04 (2) | 2.67 (2) | 3.381 (2) | 125.5 (16) |
C20—H20B···O5iv | 0.99 | 2.43 | 3.332 (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
C23H29NO6 | F(000) = 1776 |
Mr = 415.47 | Dx = 1.330 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.8854 (4) Å | Cell parameters from 9684 reflections |
b = 25.2446 (10) Å | θ = 2.7–30.5° |
c = 15.3665 (6) Å | µ = 0.10 mm−1 |
β = 100.7606 (19)° | T = 100 K |
V = 4148.4 (3) Å3 | Prism, colourless |
Z = 8 | 0.48 × 0.43 × 0.31 mm |
Data collection top
Bruker SMART BREEZE CCD diffractometer | Rint = 0.045 |
φ and ω scans | θmax = 30.6°, θmin = 1.6° |
168826 measured reflections | h = −15→15 |
12707 independent reflections | k = −36→36 |
11044 reflections with I > 2σ(I) | l = −21→21 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.039 | H 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 reflections | Δρmax = 0.52 e Å−3 |
569 parameters | Δρmin = −0.20 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1A | 0.09761 (6) | 0.68726 (3) | 0.28219 (5) | 0.01536 (13) | |
O2A | 0.66193 (6) | 0.61973 (3) | 0.32843 (5) | 0.01652 (13) | |
O3A | 0.54423 (6) | 0.69363 (3) | 0.31163 (5) | 0.01527 (13) | |
O4A | 0.40914 (7) | 0.74895 (3) | 0.70657 (5) | 0.01676 (14) | |
H4C | 0.4593 (16) | 0.7750 (7) | 0.7112 (11) | 0.035 (4)* | |
O5A | 0.31079 (7) | 0.65461 (3) | 0.68643 (4) | 0.01866 (14) | |
O6A | 0.47618 (6) | 0.80349 (3) | 0.56333 (5) | 0.01668 (14) | |
N1A | 0.34484 (7) | 0.54131 (3) | 0.39339 (5) | 0.01093 (13) | |
H1A | 0.3460 (13) | 0.5068 (6) | 0.4013 (9) | 0.021 (3)* | |
C2A | 0.45480 (8) | 0.56515 (3) | 0.38033 (5) | 0.01037 (15) | |
C3A | 0.45444 (8) | 0.61775 (3) | 0.36062 (6) | 0.01007 (14) | |
C4A | 0.33953 (8) | 0.65156 (3) | 0.36544 (5) | 0.00946 (14) | |
H4B | 0.332567 | 0.679421 | 0.318505 | 0.011* | |
C5A | 0.22391 (8) | 0.61725 (3) | 0.34576 (5) | 0.00925 (14) | |
C6A | 0.10568 (8) | 0.63990 (3) | 0.30421 (5) | 0.00999 (14) | |
C7A | −0.00768 (8) | 0.60412 (3) | 0.28469 (6) | 0.01162 (15) | |
H7C | −0.013501 | 0.588937 | 0.224662 | 0.014* | |
H7D | −0.083739 | 0.625617 | 0.284713 | 0.014* | |
C8A | −0.00446 (8) | 0.55865 (3) | 0.35161 (6) | 0.01072 (15) | |
C9A | 0.11952 (8) | 0.52866 (3) | 0.35798 (6) | 0.01071 (15) | |
H9C | 0.130811 | 0.504944 | 0.410176 | 0.013* | |
H9D | 0.115282 | 0.506253 | 0.304626 | 0.013* | |
C10A | 0.23072 (8) | 0.56462 (3) | 0.36583 (5) | 0.00927 (14) | |
C11A | −0.01825 (9) | 0.58146 (4) | 0.44184 (6) | 0.01572 (17) | |
H11D | 0.049914 | 0.606478 | 0.462131 | 0.024* | |
H11E | −0.014841 | 0.552601 | 0.484888 | 0.024* | |
H11F | −0.098635 | 0.599854 | 0.436132 | 0.024* | |
C12A | −0.11296 (9) | 0.52050 (4) | 0.31995 (7) | 0.01625 (17) | |
H12D | −0.192403 | 0.539584 | 0.314712 | 0.024* | |
H12E | −0.110612 | 0.491581 | 0.362771 | 0.024* | |
H12F | −0.105306 | 0.505920 | 0.262095 | 0.024* | |
C13A | 0.56241 (8) | 0.52727 (4) | 0.38723 (6) | 0.01339 (16) | |
H13D | 0.543503 | 0.494967 | 0.417571 | 0.020* | |
H13E | 0.638014 | 0.543801 | 0.420913 | 0.020* | |
H13F | 0.575997 | 0.518286 | 0.327703 | 0.020* | |
C14A | 0.56421 (8) | 0.64179 (4) | 0.33347 (6) | 0.01162 (15) | |
C15A | 0.63909 (9) | 0.71842 (4) | 0.27011 (6) | 0.01674 (17) | |
H15C | 0.723206 | 0.707623 | 0.301464 | 0.020* | |
H15D | 0.632745 | 0.757422 | 0.274256 | 0.020* | |
C16A | 0.62173 (10) | 0.70211 (4) | 0.17397 (7) | 0.02087 (19) | |
H16D | 0.674331 | 0.724303 | 0.143533 | 0.031* | |
H16E | 0.533831 | 0.706570 | 0.145851 | 0.031* | |
H16F | 0.645760 | 0.664893 | 0.170167 | 0.031* | |
C17A | 0.35248 (8) | 0.67935 (3) | 0.45549 (6) | 0.01023 (15) | |
C18A | 0.32110 (8) | 0.65290 (3) | 0.52864 (6) | 0.01201 (15) | |
H18A | 0.286818 | 0.618226 | 0.521374 | 0.014* | |
C19A | 0.33951 (8) | 0.67677 (4) | 0.61162 (6) | 0.01263 (16) | |
C20A | 0.39194 (8) | 0.72784 (4) | 0.62385 (6) | 0.01266 (16) | |
C21A | 0.42098 (8) | 0.75402 (3) | 0.55069 (6) | 0.01235 (16) | |
C22A | 0.40129 (8) | 0.73027 (3) | 0.46704 (6) | 0.01162 (15) | |
H22A | 0.421364 | 0.749009 | 0.417934 | 0.014* | |
C23A | 0.25765 (10) | 0.60304 (4) | 0.67836 (7) | 0.02005 (19) | |
H23D | 0.179341 | 0.603652 | 0.634894 | 0.030* | |
H23E | 0.240715 | 0.591604 | 0.735908 | 0.030* | |
H23F | 0.316250 | 0.578294 | 0.658694 | 0.030* | |
C24A | 0.38733 (10) | 0.84600 (4) | 0.54853 (7) | 0.02017 (19) | |
H24D | 0.337479 | 0.843172 | 0.488624 | 0.030* | |
H24E | 0.431736 | 0.879953 | 0.554867 | 0.030* | |
H24F | 0.332068 | 0.843913 | 0.591977 | 0.030* | |
O1B | 0.64618 (7) | 0.56795 (3) | 0.59302 (5) | 0.01898 (14) | |
O2B | 0.42404 (7) | 0.61173 (3) | 0.93863 (5) | 0.02210 (15) | |
O3B | 0.47350 (6) | 0.54093 (3) | 0.86392 (5) | 0.01724 (14) | |
O4B | 1.07150 (7) | 0.47496 (3) | 0.91945 (5) | 0.01745 (14) | |
H4 | 1.1277 (17) | 0.4973 (7) | 0.9396 (12) | 0.040 (5)* | |
O5B | 1.09254 (6) | 0.57723 (3) | 0.88846 (5) | 0.01832 (14) | |
O6B | 0.85544 (7) | 0.42479 (3) | 0.88741 (5) | 0.01802 (14) | |
N1B | 0.67195 (7) | 0.70086 (3) | 0.81054 (5) | 0.01272 (14) | |
H1 | 0.6769 (13) | 0.7356 (6) | 0.8200 (9) | 0.022 (3)* | |
C2B | 0.60016 (8) | 0.67286 (4) | 0.86093 (6) | 0.01315 (16) | |
C3B | 0.57467 (8) | 0.62086 (4) | 0.84315 (6) | 0.01213 (15) | |
C4B | 0.63347 (8) | 0.59179 (3) | 0.77391 (6) | 0.01085 (15) | |
H4A | 0.570391 | 0.566145 | 0.742480 | 0.013* | |
C5B | 0.66228 (8) | 0.63135 (3) | 0.70649 (6) | 0.01071 (15) | |
C6B | 0.66639 (8) | 0.61434 (3) | 0.61710 (6) | 0.01161 (15) | |
C7B | 0.69106 (8) | 0.65543 (3) | 0.55138 (6) | 0.01271 (15) | |
H7A | 0.610642 | 0.671873 | 0.523744 | 0.015* | |
H7B | 0.725884 | 0.637650 | 0.503929 | 0.015* | |
C8B | 0.78141 (8) | 0.69911 (3) | 0.59211 (6) | 0.01258 (15) | |
C9B | 0.73133 (8) | 0.72350 (3) | 0.67009 (6) | 0.01263 (15) | |
H9A | 0.798126 | 0.745108 | 0.705925 | 0.015* | |
H9B | 0.660884 | 0.747437 | 0.646616 | 0.015* | |
C10B | 0.68745 (8) | 0.68288 (3) | 0.72894 (6) | 0.01098 (15) | |
C11B | 0.91219 (9) | 0.67533 (4) | 0.62358 (7) | 0.01783 (18) | |
H11A | 0.906685 | 0.645916 | 0.664297 | 0.027* | |
H11B | 0.968228 | 0.702619 | 0.654158 | 0.027* | |
H11C | 0.945007 | 0.662303 | 0.572359 | 0.027* | |
C12B | 0.78685 (10) | 0.74186 (4) | 0.52223 (7) | 0.01908 (18) | |
H12A | 0.817987 | 0.726305 | 0.472081 | 0.029* | |
H12B | 0.843131 | 0.770322 | 0.548282 | 0.029* | |
H12C | 0.702898 | 0.756306 | 0.501600 | 0.029* | |
C13B | 0.55601 (10) | 0.70687 (4) | 0.92881 (7) | 0.02043 (19) | |
H13A | 0.617141 | 0.735037 | 0.947664 | 0.031* | |
H13B | 0.546865 | 0.685161 | 0.980088 | 0.031* | |
H13C | 0.475127 | 0.722665 | 0.903090 | 0.031* | |
C14B | 0.48511 (8) | 0.59282 (4) | 0.88766 (6) | 0.01479 (16) | |
C15B | 0.37849 (9) | 0.51189 (4) | 0.89925 (7) | 0.01923 (18) | |
H15A | 0.294455 | 0.525795 | 0.873705 | 0.023* | |
H15B | 0.392024 | 0.516062 | 0.964409 | 0.023* | |
C16B | 0.38731 (10) | 0.45419 (4) | 0.87558 (7) | 0.02153 (19) | |
H16A | 0.376740 | 0.450555 | 0.811117 | 0.032* | |
H16B | 0.321567 | 0.434209 | 0.896828 | 0.032* | |
H16C | 0.469351 | 0.440325 | 0.903427 | 0.032* | |
C17B | 0.75057 (8) | 0.56042 (3) | 0.81518 (6) | 0.01136 (15) | |
C18B | 0.86636 (8) | 0.58599 (4) | 0.83344 (6) | 0.01318 (16) | |
H18 | 0.871998 | 0.622799 | 0.821919 | 0.016* | |
C19B | 0.97326 (8) | 0.55741 (4) | 0.86850 (6) | 0.01334 (16) | |
C20B | 0.96602 (8) | 0.50345 (4) | 0.88589 (6) | 0.01323 (16) | |
C21B | 0.85061 (9) | 0.47788 (3) | 0.86888 (6) | 0.01301 (16) | |
C22B | 0.74257 (8) | 0.50638 (4) | 0.83344 (6) | 0.01278 (16) | |
H22 | 0.663772 | 0.489024 | 0.821767 | 0.015* | |
C23B | 1.10806 (9) | 0.63320 (4) | 0.88435 (8) | 0.02108 (19) | |
H23A | 1.077197 | 0.645485 | 0.823712 | 0.032* | |
H23B | 1.196897 | 0.642070 | 0.901795 | 0.032* | |
H23C | 1.060743 | 0.650516 | 0.924718 | 0.032* | |
C24B | 0.74049 (10) | 0.39706 (4) | 0.88304 (7) | 0.01957 (19) | |
H24A | 0.689946 | 0.400674 | 0.823490 | 0.029* | |
H24B | 0.694746 | 0.411935 | 0.926559 | 0.029* | |
H24C | 0.757687 | 0.359498 | 0.896071 | 0.029* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0138 (3) | 0.0100 (3) | 0.0212 (3) | 0.0012 (2) | 0.0004 (2) | 0.0044 (2) |
O2A | 0.0114 (3) | 0.0183 (3) | 0.0206 (3) | 0.0018 (2) | 0.0049 (2) | 0.0016 (3) |
O3A | 0.0153 (3) | 0.0116 (3) | 0.0209 (3) | −0.0018 (2) | 0.0086 (3) | 0.0018 (2) |
O4A | 0.0174 (3) | 0.0172 (3) | 0.0155 (3) | −0.0066 (3) | 0.0026 (2) | −0.0073 (2) |
O5A | 0.0266 (4) | 0.0172 (3) | 0.0127 (3) | −0.0096 (3) | 0.0049 (3) | −0.0020 (2) |
O6A | 0.0150 (3) | 0.0086 (3) | 0.0256 (3) | −0.0037 (2) | 0.0018 (3) | −0.0039 (2) |
N1A | 0.0099 (3) | 0.0076 (3) | 0.0152 (3) | 0.0012 (2) | 0.0019 (3) | 0.0017 (3) |
C2A | 0.0098 (3) | 0.0115 (4) | 0.0096 (3) | 0.0008 (3) | 0.0012 (3) | −0.0006 (3) |
C3A | 0.0088 (3) | 0.0107 (3) | 0.0106 (3) | 0.0002 (3) | 0.0017 (3) | −0.0005 (3) |
C4A | 0.0087 (3) | 0.0078 (3) | 0.0117 (3) | −0.0001 (3) | 0.0014 (3) | 0.0002 (3) |
C5A | 0.0088 (3) | 0.0084 (3) | 0.0104 (3) | 0.0001 (3) | 0.0016 (3) | 0.0004 (3) |
C6A | 0.0101 (3) | 0.0097 (3) | 0.0102 (3) | 0.0007 (3) | 0.0020 (3) | 0.0005 (3) |
C7A | 0.0095 (3) | 0.0113 (4) | 0.0134 (4) | −0.0005 (3) | 0.0004 (3) | 0.0006 (3) |
C8A | 0.0096 (3) | 0.0098 (3) | 0.0130 (4) | −0.0010 (3) | 0.0027 (3) | −0.0007 (3) |
C9A | 0.0102 (3) | 0.0081 (3) | 0.0138 (4) | −0.0010 (3) | 0.0024 (3) | −0.0005 (3) |
C10A | 0.0095 (3) | 0.0092 (3) | 0.0090 (3) | 0.0005 (3) | 0.0014 (3) | −0.0003 (3) |
C11A | 0.0166 (4) | 0.0174 (4) | 0.0146 (4) | −0.0002 (3) | 0.0064 (3) | −0.0019 (3) |
C12A | 0.0119 (4) | 0.0147 (4) | 0.0220 (4) | −0.0042 (3) | 0.0026 (3) | −0.0009 (3) |
C13A | 0.0118 (4) | 0.0126 (4) | 0.0159 (4) | 0.0035 (3) | 0.0031 (3) | 0.0003 (3) |
C14A | 0.0113 (4) | 0.0126 (4) | 0.0107 (3) | −0.0014 (3) | 0.0015 (3) | −0.0008 (3) |
C15A | 0.0160 (4) | 0.0162 (4) | 0.0195 (4) | −0.0051 (3) | 0.0072 (3) | 0.0022 (3) |
C16A | 0.0203 (5) | 0.0245 (5) | 0.0190 (4) | −0.0016 (4) | 0.0066 (4) | 0.0024 (4) |
C17A | 0.0086 (3) | 0.0089 (3) | 0.0130 (4) | 0.0004 (3) | 0.0014 (3) | −0.0009 (3) |
C18A | 0.0124 (4) | 0.0098 (4) | 0.0136 (4) | −0.0019 (3) | 0.0020 (3) | −0.0013 (3) |
C19A | 0.0124 (4) | 0.0120 (4) | 0.0135 (4) | −0.0022 (3) | 0.0024 (3) | −0.0008 (3) |
C20A | 0.0104 (4) | 0.0123 (4) | 0.0149 (4) | −0.0013 (3) | 0.0015 (3) | −0.0040 (3) |
C21A | 0.0100 (4) | 0.0082 (3) | 0.0185 (4) | −0.0016 (3) | 0.0017 (3) | −0.0027 (3) |
C22A | 0.0107 (3) | 0.0091 (3) | 0.0150 (4) | −0.0004 (3) | 0.0023 (3) | −0.0003 (3) |
C23A | 0.0280 (5) | 0.0149 (4) | 0.0177 (4) | −0.0065 (4) | 0.0052 (4) | 0.0013 (3) |
C24A | 0.0219 (5) | 0.0102 (4) | 0.0281 (5) | 0.0000 (3) | 0.0039 (4) | −0.0003 (3) |
O1B | 0.0299 (4) | 0.0093 (3) | 0.0169 (3) | −0.0001 (3) | 0.0023 (3) | −0.0026 (2) |
O2B | 0.0220 (4) | 0.0223 (4) | 0.0258 (4) | 0.0014 (3) | 0.0142 (3) | 0.0004 (3) |
O3B | 0.0148 (3) | 0.0159 (3) | 0.0229 (3) | −0.0016 (2) | 0.0082 (3) | 0.0013 (3) |
O4B | 0.0143 (3) | 0.0165 (3) | 0.0203 (3) | 0.0059 (3) | 0.0001 (3) | 0.0028 (3) |
O5B | 0.0112 (3) | 0.0149 (3) | 0.0272 (4) | 0.0005 (2) | −0.0007 (3) | −0.0011 (3) |
O6B | 0.0181 (3) | 0.0111 (3) | 0.0256 (4) | 0.0029 (2) | 0.0060 (3) | 0.0060 (3) |
N1B | 0.0151 (3) | 0.0098 (3) | 0.0137 (3) | 0.0001 (3) | 0.0038 (3) | −0.0031 (3) |
C2B | 0.0121 (4) | 0.0147 (4) | 0.0128 (4) | 0.0025 (3) | 0.0027 (3) | −0.0008 (3) |
C3B | 0.0101 (4) | 0.0136 (4) | 0.0129 (4) | 0.0022 (3) | 0.0026 (3) | 0.0010 (3) |
C4B | 0.0107 (4) | 0.0095 (3) | 0.0123 (4) | 0.0011 (3) | 0.0017 (3) | 0.0001 (3) |
C5B | 0.0105 (3) | 0.0094 (3) | 0.0119 (4) | 0.0012 (3) | 0.0014 (3) | −0.0003 (3) |
C6B | 0.0113 (4) | 0.0099 (4) | 0.0128 (4) | 0.0016 (3) | 0.0001 (3) | −0.0009 (3) |
C7B | 0.0147 (4) | 0.0114 (4) | 0.0117 (4) | −0.0004 (3) | 0.0017 (3) | −0.0008 (3) |
C8B | 0.0127 (4) | 0.0122 (4) | 0.0131 (4) | −0.0004 (3) | 0.0032 (3) | −0.0011 (3) |
C9B | 0.0143 (4) | 0.0093 (4) | 0.0147 (4) | −0.0006 (3) | 0.0037 (3) | −0.0013 (3) |
C10B | 0.0098 (3) | 0.0107 (4) | 0.0122 (4) | 0.0015 (3) | 0.0014 (3) | −0.0011 (3) |
C11B | 0.0133 (4) | 0.0205 (4) | 0.0197 (4) | 0.0007 (3) | 0.0032 (3) | −0.0036 (3) |
C12B | 0.0230 (5) | 0.0174 (4) | 0.0177 (4) | −0.0045 (4) | 0.0061 (4) | 0.0020 (3) |
C13B | 0.0250 (5) | 0.0196 (5) | 0.0191 (4) | 0.0027 (4) | 0.0105 (4) | −0.0044 (4) |
C14B | 0.0122 (4) | 0.0162 (4) | 0.0162 (4) | 0.0020 (3) | 0.0030 (3) | 0.0030 (3) |
C15B | 0.0148 (4) | 0.0195 (4) | 0.0252 (5) | −0.0026 (3) | 0.0082 (4) | 0.0042 (4) |
C16B | 0.0210 (5) | 0.0193 (5) | 0.0244 (5) | −0.0038 (4) | 0.0046 (4) | 0.0020 (4) |
C17B | 0.0117 (4) | 0.0108 (4) | 0.0116 (4) | 0.0020 (3) | 0.0023 (3) | −0.0005 (3) |
C18B | 0.0131 (4) | 0.0106 (4) | 0.0152 (4) | 0.0014 (3) | 0.0012 (3) | −0.0006 (3) |
C19B | 0.0118 (4) | 0.0138 (4) | 0.0140 (4) | 0.0009 (3) | 0.0012 (3) | −0.0016 (3) |
C20B | 0.0138 (4) | 0.0139 (4) | 0.0119 (4) | 0.0046 (3) | 0.0021 (3) | 0.0008 (3) |
C21B | 0.0166 (4) | 0.0107 (4) | 0.0126 (4) | 0.0028 (3) | 0.0049 (3) | 0.0016 (3) |
C22B | 0.0135 (4) | 0.0120 (4) | 0.0134 (4) | 0.0015 (3) | 0.0041 (3) | 0.0004 (3) |
C23B | 0.0156 (4) | 0.0162 (4) | 0.0307 (5) | −0.0016 (3) | 0.0025 (4) | −0.0033 (4) |
C24B | 0.0213 (5) | 0.0145 (4) | 0.0243 (5) | −0.0009 (3) | 0.0078 (4) | 0.0041 (3) |
Geometric parameters (Å, º) top
O1A—C6A | 1.2412 (10) | O1B—C6B | 1.2355 (11) |
O2A—C14A | 1.2159 (11) | O2B—C14B | 1.2156 (12) |
O3A—C14A | 1.3583 (11) | O3B—C14B | 1.3593 (12) |
O3A—C15A | 1.4529 (11) | O3B—C15B | 1.4530 (11) |
O4A—C20A | 1.3587 (11) | O4B—C20B | 1.3713 (11) |
O5A—C19A | 1.3661 (11) | O5B—C19B | 1.3717 (11) |
O5A—C23A | 1.4206 (12) | O5B—C23B | 1.4257 (12) |
O6A—C21A | 1.3837 (10) | O6B—C21B | 1.3690 (11) |
O6A—C24A | 1.4341 (12) | O6B—C24B | 1.4245 (12) |
N1A—C2A | 1.3874 (11) | N1B—C2B | 1.3913 (12) |
N1A—C10A | 1.3683 (11) | N1B—C10B | 1.3733 (11) |
C2A—C3A | 1.3617 (12) | C2B—C3B | 1.3589 (13) |
C2A—C13A | 1.5006 (12) | C2B—C13B | 1.4979 (13) |
C3A—C4A | 1.5275 (12) | C3B—C4B | 1.5280 (12) |
C3A—C14A | 1.4684 (12) | C3B—C14B | 1.4725 (13) |
C4A—C5A | 1.5112 (11) | C4B—C5B | 1.5134 (12) |
C4A—C17A | 1.5344 (12) | C4B—C17B | 1.5337 (12) |
C5A—C6A | 1.4437 (11) | C5B—C6B | 1.4479 (12) |
C5A—C10A | 1.3628 (11) | C5B—C10B | 1.3604 (12) |
C6A—C7A | 1.5134 (12) | C6B—C7B | 1.5062 (12) |
C7A—C8A | 1.5371 (12) | C7B—C8B | 1.5314 (12) |
C8A—C9A | 1.5346 (12) | C8B—C9B | 1.5350 (12) |
C8A—C11A | 1.5342 (12) | C8B—C11B | 1.5374 (13) |
C8A—C12A | 1.5313 (12) | C8B—C12B | 1.5313 (13) |
C9A—C10A | 1.4998 (11) | C9B—C10B | 1.5027 (12) |
C15A—C16A | 1.5111 (14) | C15B—C16B | 1.5088 (15) |
C17A—C18A | 1.4034 (12) | C17B—C18B | 1.3972 (12) |
C17A—C22A | 1.3895 (11) | C17B—C22B | 1.3987 (12) |
C18A—C19A | 1.3906 (12) | C18B—C19B | 1.3896 (12) |
C19A—C20A | 1.4082 (12) | C19B—C20B | 1.3932 (13) |
C20A—C21A | 1.3904 (13) | C20B—C21B | 1.3931 (13) |
C21A—C22A | 1.3981 (12) | C21B—C22B | 1.3994 (12) |
| | | |
C14A—O3A—C15A | 115.43 (7) | C14B—O3B—C15B | 115.02 (7) |
C19A—O5A—C23A | 117.08 (7) | C19B—O5B—C23B | 117.82 (7) |
C21A—O6A—C24A | 113.00 (7) | C21B—O6B—C24B | 118.16 (7) |
C10A—N1A—C2A | 121.78 (7) | C10B—N1B—C2B | 121.19 (8) |
N1A—C2A—C13A | 113.36 (7) | N1B—C2B—C13B | 112.51 (8) |
C3A—C2A—N1A | 119.23 (8) | C3B—C2B—N1B | 119.59 (8) |
C3A—C2A—C13A | 127.37 (8) | C3B—C2B—C13B | 127.86 (9) |
C2A—C3A—C4A | 120.17 (7) | C2B—C3B—C4B | 120.50 (8) |
C2A—C3A—C14A | 119.84 (8) | C2B—C3B—C14B | 119.94 (8) |
C14A—C3A—C4A | 119.99 (7) | C14B—C3B—C4B | 119.50 (8) |
C3A—C4A—C17A | 111.17 (7) | C3B—C4B—C17B | 112.57 (7) |
C5A—C4A—C3A | 109.20 (7) | C5B—C4B—C3B | 109.09 (7) |
C5A—C4A—C17A | 112.05 (7) | C5B—C4B—C17B | 111.19 (7) |
C6A—C5A—C4A | 120.12 (7) | C6B—C5B—C4B | 120.05 (7) |
C10A—C5A—C4A | 120.36 (7) | C10B—C5B—C4B | 121.01 (8) |
C10A—C5A—C6A | 119.51 (7) | C10B—C5B—C6B | 118.93 (8) |
O1A—C6A—C5A | 120.93 (8) | O1B—C6B—C5B | 122.00 (8) |
O1A—C6A—C7A | 120.49 (8) | O1B—C6B—C7B | 119.74 (8) |
C5A—C6A—C7A | 118.54 (7) | C5B—C6B—C7B | 118.21 (7) |
C6A—C7A—C8A | 113.41 (7) | C6B—C7B—C8B | 113.78 (7) |
C9A—C8A—C7A | 108.72 (7) | C7B—C8B—C9B | 108.25 (7) |
C11A—C8A—C7A | 109.30 (7) | C7B—C8B—C11B | 109.50 (7) |
C11A—C8A—C9A | 111.15 (7) | C9B—C8B—C11B | 110.73 (7) |
C12A—C8A—C7A | 109.71 (7) | C12B—C8B—C7B | 109.08 (7) |
C12A—C8A—C9A | 109.08 (7) | C12B—C8B—C9B | 109.31 (7) |
C12A—C8A—C11A | 108.87 (7) | C12B—C8B—C11B | 109.94 (8) |
C10A—C9A—C8A | 113.17 (7) | C10B—C9B—C8B | 113.28 (7) |
N1A—C10A—C9A | 115.91 (7) | N1B—C10B—C9B | 115.54 (7) |
C5A—C10A—N1A | 119.81 (8) | C5B—C10B—N1B | 119.61 (8) |
C5A—C10A—C9A | 124.26 (7) | C5B—C10B—C9B | 124.85 (8) |
O2A—C14A—O3A | 121.80 (8) | O2B—C14B—O3B | 121.11 (9) |
O2A—C14A—C3A | 126.64 (8) | O2B—C14B—C3B | 126.85 (9) |
O3A—C14A—C3A | 111.55 (7) | O3B—C14B—C3B | 112.03 (8) |
O3A—C15A—C16A | 110.04 (8) | O3B—C15B—C16B | 108.38 (8) |
C18A—C17A—C4A | 120.65 (7) | C18B—C17B—C4B | 119.57 (8) |
C22A—C17A—C4A | 120.45 (8) | C18B—C17B—C22B | 119.86 (8) |
C22A—C17A—C18A | 118.83 (8) | C22B—C17B—C4B | 120.56 (8) |
C19A—C18A—C17A | 120.88 (8) | C19B—C18B—C17B | 119.78 (8) |
O5A—C19A—C18A | 125.29 (8) | O5B—C19B—C18B | 125.90 (8) |
O5A—C19A—C20A | 114.41 (8) | O5B—C19B—C20B | 113.51 (8) |
C18A—C19A—C20A | 120.30 (8) | C18B—C19B—C20B | 120.59 (8) |
O4A—C20A—C19A | 117.75 (8) | O4B—C20B—C19B | 120.77 (8) |
O4A—C20A—C21A | 123.89 (8) | O4B—C20B—C21B | 119.34 (8) |
C21A—C20A—C19A | 118.35 (8) | C21B—C20B—C19B | 119.89 (8) |
O6A—C21A—C20A | 118.27 (8) | O6B—C21B—C20B | 114.60 (8) |
O6A—C21A—C22A | 120.27 (8) | O6B—C21B—C22B | 125.54 (8) |
C20A—C21A—C22A | 121.37 (8) | C20B—C21B—C22B | 119.85 (8) |
C17A—C22A—C21A | 120.23 (8) | C17B—C22B—C21B | 120.02 (8) |
| | | |
O1A—C6A—C7A—C8A | −151.01 (8) | O1B—C6B—C7B—C8B | −147.46 (8) |
O4A—C20A—C21A—O6A | 3.22 (13) | O4B—C20B—C21B—O6B | −0.68 (12) |
O4A—C20A—C21A—C22A | 179.97 (8) | O4B—C20B—C21B—C22B | −179.08 (8) |
O5A—C19A—C20A—O4A | 0.60 (12) | O5B—C19B—C20B—O4B | −0.23 (12) |
O5A—C19A—C20A—C21A | −178.29 (8) | O5B—C19B—C20B—C21B | 179.96 (8) |
O6A—C21A—C22A—C17A | 176.30 (8) | O6B—C21B—C22B—C17B | −178.23 (8) |
N1A—C2A—C3A—C4A | 8.37 (12) | N1B—C2B—C3B—C4B | 5.35 (13) |
N1A—C2A—C3A—C14A | −170.77 (8) | N1B—C2B—C3B—C14B | −171.69 (8) |
C2A—N1A—C10A—C5A | −16.97 (12) | C2B—N1B—C10B—C5B | −17.81 (13) |
C2A—N1A—C10A—C9A | 161.69 (8) | C2B—N1B—C10B—C9B | 161.71 (8) |
C2A—C3A—C4A—C5A | −29.30 (10) | C2B—C3B—C4B—C5B | −26.83 (11) |
C2A—C3A—C4A—C17A | 94.83 (9) | C2B—C3B—C4B—C17B | 97.09 (10) |
C2A—C3A—C14A—O2A | −2.27 (14) | C2B—C3B—C14B—O2B | 3.16 (15) |
C2A—C3A—C14A—O3A | 176.45 (8) | C2B—C3B—C14B—O3B | −178.35 (8) |
C3A—C4A—C5A—C6A | −149.71 (8) | C3B—C4B—C5B—C6B | −153.27 (8) |
C3A—C4A—C5A—C10A | 29.31 (10) | C3B—C4B—C5B—C10B | 28.25 (11) |
C3A—C4A—C17A—C18A | −83.76 (9) | C3B—C4B—C17B—C18B | −84.89 (10) |
C3A—C4A—C17A—C22A | 93.08 (9) | C3B—C4B—C17B—C22B | 96.04 (9) |
C4A—C3A—C14A—O2A | 178.59 (8) | C4B—C3B—C14B—O2B | −173.92 (9) |
C4A—C3A—C14A—O3A | −2.69 (11) | C4B—C3B—C14B—O3B | 4.58 (11) |
C4A—C5A—C6A—O1A | 1.72 (12) | C4B—C5B—C6B—O1B | 0.45 (13) |
C4A—C5A—C6A—C7A | 179.35 (7) | C4B—C5B—C6B—C7B | 177.94 (7) |
C4A—C5A—C10A—N1A | −8.32 (12) | C4B—C5B—C10B—N1B | −7.91 (12) |
C4A—C5A—C10A—C9A | 173.14 (7) | C4B—C5B—C10B—C9B | 172.62 (8) |
C4A—C17A—C18A—C19A | 176.22 (8) | C4B—C17B—C18B—C19B | −178.18 (8) |
C4A—C17A—C22A—C21A | −175.56 (8) | C4B—C17B—C22B—C21B | 178.27 (8) |
C5A—C4A—C17A—C18A | 38.74 (10) | C5B—C4B—C17B—C18B | 37.86 (11) |
C5A—C4A—C17A—C22A | −144.43 (8) | C5B—C4B—C17B—C22B | −141.21 (8) |
C5A—C6A—C7A—C8A | 31.35 (11) | C5B—C6B—C7B—C8B | 34.99 (11) |
C6A—C5A—C10A—N1A | 170.71 (8) | C6B—C5B—C10B—N1B | 173.59 (8) |
C6A—C5A—C10A—C9A | −7.84 (12) | C6B—C5B—C10B—C9B | −5.88 (13) |
C6A—C7A—C8A—C9A | −53.22 (9) | C6B—C7B—C8B—C9B | −54.30 (10) |
C6A—C7A—C8A—C11A | 68.27 (9) | C6B—C7B—C8B—C11B | 66.51 (10) |
C6A—C7A—C8A—C12A | −172.43 (7) | C6B—C7B—C8B—C12B | −173.14 (8) |
C7A—C8A—C9A—C10A | 45.78 (9) | C7B—C8B—C9B—C10B | 44.60 (10) |
C8A—C9A—C10A—N1A | 164.48 (7) | C8B—C9B—C10B—N1B | 164.10 (8) |
C8A—C9A—C10A—C5A | −16.93 (12) | C8B—C9B—C10B—C5B | −16.41 (12) |
C10A—N1A—C2A—C3A | 16.82 (12) | C10B—N1B—C2B—C3B | 19.06 (13) |
C10A—N1A—C2A—C13A | −161.19 (8) | C10B—N1B—C2B—C13B | −158.87 (8) |
C10A—C5A—C6A—O1A | −177.31 (8) | C10B—C5B—C6B—O1B | 178.96 (9) |
C10A—C5A—C6A—C7A | 0.32 (12) | C10B—C5B—C6B—C7B | −3.55 (12) |
C11A—C8A—C9A—C10A | −74.57 (9) | C11B—C8B—C9B—C10B | −75.44 (9) |
C12A—C8A—C9A—C10A | 165.38 (7) | C12B—C8B—C9B—C10B | 163.30 (8) |
C13A—C2A—C3A—C4A | −173.92 (8) | C13B—C2B—C3B—C4B | −177.07 (9) |
C13A—C2A—C3A—C14A | 6.94 (13) | C13B—C2B—C3B—C14B | 5.89 (14) |
C14A—O3A—C15A—C16A | 77.56 (10) | C14B—O3B—C15B—C16B | −173.74 (8) |
C14A—C3A—C4A—C5A | 149.84 (7) | C14B—C3B—C4B—C5B | 150.23 (8) |
C14A—C3A—C4A—C17A | −86.04 (9) | C14B—C3B—C4B—C17B | −85.86 (10) |
C15A—O3A—C14A—O2A | 8.56 (12) | C15B—O3B—C14B—O2B | 3.78 (13) |
C15A—O3A—C14A—C3A | −170.22 (7) | C15B—O3B—C14B—C3B | −174.82 (8) |
C17A—C4A—C5A—C6A | 86.68 (9) | C17B—C4B—C5B—C6B | 82.01 (10) |
C17A—C4A—C5A—C10A | −94.30 (9) | C17B—C4B—C5B—C10B | −96.48 (9) |
C17A—C18A—C19A—O5A | 179.24 (8) | C17B—C18B—C19B—O5B | 179.14 (8) |
C17A—C18A—C19A—C20A | −0.95 (13) | C17B—C18B—C19B—C20B | −0.19 (13) |
C18A—C17A—C22A—C21A | 1.33 (13) | C18B—C17B—C22B—C21B | −0.80 (13) |
C18A—C19A—C20A—O4A | −179.24 (8) | C18B—C19B—C20B—O4B | 179.18 (8) |
C18A—C19A—C20A—C21A | 1.87 (13) | C18B—C19B—C20B—C21B | −0.63 (13) |
C19A—C20A—C21A—O6A | −177.97 (8) | C19B—C20B—C21B—O6B | 179.13 (8) |
C19A—C20A—C21A—C22A | −1.22 (13) | C19B—C20B—C21B—C22B | 0.72 (13) |
C20A—C21A—C22A—C17A | −0.39 (13) | C20B—C21B—C22B—C17B | −0.02 (13) |
C22A—C17A—C18A—C19A | −0.67 (13) | C22B—C17B—C18B—C19B | 0.89 (13) |
C23A—O5A—C19A—C18A | −0.11 (14) | C23B—O5B—C19B—C18B | 8.86 (14) |
C23A—O5A—C19A—C20A | −179.94 (8) | C23B—O5B—C19B—C20B | −171.77 (9) |
C24A—O6A—C21A—C20A | −93.57 (10) | C24B—O6B—C21B—C20B | 171.90 (8) |
C24A—O6A—C21A—C22A | 89.64 (10) | C24B—O6B—C21B—C22B | −9.80 (13) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4A—H4C···O1Ai | 0.848 (17) | 1.937 (17) | 2.6948 (9) | 148.0 (16) |
N1A—H1A···O1Bii | 0.880 (15) | 1.890 (15) | 2.7666 (10) | 174.1 (13) |
C7A—H7C···O6Bii | 0.99 | 2.67 | 3.4510 (12) | 136 |
C12A—H12D···O2Aiii | 0.98 | 2.60 | 3.5237 (12) | 157 |
C13A—H13D···O1Bii | 0.98 | 2.59 | 3.3590 (12) | 136 |
C16A—H16D···O4Aiv | 0.98 | 2.65 | 3.3136 (13) | 126 |
C24A—H24E···O4Bv | 0.98 | 2.43 | 3.3105 (13) | 149 |
N1B—H1···O1Ai | 0.888 (15) | 2.166 (15) | 2.9479 (10) | 146.6 (12) |
C7B—H7B···O2A | 0.99 | 2.69 | 3.4992 (11) | 139 |
C9B—H9B···O6A | 0.99 | 2.59 | 3.5751 (11) | 172 |
C15B—H15A···O5Biii | 0.99 | 2.60 | 3.4993 (12) | 151 |
C23B—H23B···O2Bvi | 0.98 | 2.55 | 3.4277 (13) | 149 |
Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z; (iv) x+1/2, −y+3/2, z−1/2; (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
C29H29NO3 | F(000) = 936 |
Mr = 439.53 | Dx = 1.229 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 11.6527 (3) Å | Cell parameters from 9872 reflections |
b = 18.1986 (4) Å | θ = 2.2–27.6° |
c = 12.3435 (3) Å | µ = 0.08 mm−1 |
β = 114.8758 (12)° | T = 100 K |
V = 2374.74 (10) Å3 | Prism, yellow |
Z = 4 | 0.45 × 0.12 × 0.11 mm |
Data collection top
Bruker SMART BREEZE CCD diffractometer | Rint = 0.055 |
φ and ω scans | θmax = 28.3°, θmin = 2.1° |
72579 measured reflections | h = −15→15 |
5902 independent reflections | k = −24→24 |
4515 reflections with I > 2σ(I) | l = −16→16 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.048 | H 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 reflections | Δρmax = 0.54 e Å−3 |
306 parameters | Δρmin = −0.22 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.34009 (10) | 0.80683 (6) | 0.16928 (9) | 0.0235 (2) | |
O2 | 0.31457 (11) | 0.54998 (7) | 0.51900 (11) | 0.0331 (3) | |
O3 | 0.19449 (10) | 0.64051 (6) | 0.40339 (10) | 0.0256 (2) | |
N1 | 0.61943 (12) | 0.65569 (7) | 0.47273 (11) | 0.0182 (3) | |
H1 | 0.6990 (19) | 0.6551 (11) | 0.5295 (18) | 0.032 (5)* | |
C2 | 0.52536 (13) | 0.62310 (7) | 0.49757 (12) | 0.0177 (3) | |
C3 | 0.40249 (13) | 0.63374 (7) | 0.42341 (12) | 0.0169 (3) | |
C4 | 0.36056 (13) | 0.68248 (7) | 0.31263 (12) | 0.0153 (3) | |
H4 | 0.304711 | 0.721153 | 0.322453 | 0.018* | |
C5 | 0.47314 (13) | 0.72274 (7) | 0.30848 (12) | 0.0152 (3) | |
C6 | 0.44911 (13) | 0.78495 (7) | 0.22944 (12) | 0.0170 (3) | |
C7 | 0.55990 (14) | 0.82620 (8) | 0.22492 (13) | 0.0202 (3) | |
H7A | 0.575271 | 0.870831 | 0.274940 | 0.024* | |
H7B | 0.536301 | 0.842425 | 0.141710 | 0.024* | |
C8 | 0.68311 (14) | 0.78268 (8) | 0.26676 (13) | 0.0199 (3) | |
C9 | 0.70717 (13) | 0.74830 (8) | 0.38790 (13) | 0.0188 (3) | |
H9A | 0.778956 | 0.713567 | 0.410903 | 0.023* | |
H9B | 0.731471 | 0.787529 | 0.449080 | 0.023* | |
C10 | 0.59379 (13) | 0.70822 (7) | 0.38663 (12) | 0.0158 (3) | |
C11 | 0.67348 (15) | 0.72310 (9) | 0.17535 (14) | 0.0260 (3) | |
H11A | 0.602860 | 0.690143 | 0.164169 | 0.039* | |
H11B | 0.752376 | 0.694870 | 0.204489 | 0.039* | |
H11C | 0.659039 | 0.746243 | 0.098998 | 0.039* | |
C12 | 0.79290 (15) | 0.83464 (9) | 0.28370 (15) | 0.0262 (3) | |
H12A | 0.872397 | 0.806942 | 0.314765 | 0.039* | |
H12B | 0.797430 | 0.873461 | 0.340391 | 0.039* | |
H12C | 0.779071 | 0.856745 | 0.206789 | 0.039* | |
C13 | 0.57721 (15) | 0.58079 (8) | 0.61266 (13) | 0.0240 (3) | |
H13A | 0.663101 | 0.597854 | 0.662873 | 0.036* | |
H13B | 0.579314 | 0.528329 | 0.595650 | 0.036* | |
H13C | 0.523073 | 0.588557 | 0.654582 | 0.036* | |
C14 | 0.30380 (14) | 0.60270 (8) | 0.45520 (13) | 0.0215 (3) | |
C15 | 0.08506 (16) | 0.61002 (11) | 0.41441 (16) | 0.0340 (4) | |
H15A | 0.023216 | 0.649703 | 0.404172 | 0.041* | |
H15B | 0.111372 | 0.589143 | 0.495409 | 0.041* | |
C16 | 0.0228 (2) | 0.55080 (12) | 0.32261 (18) | 0.0466 (5) | |
H16A | 0.080715 | 0.509048 | 0.338088 | 0.070* | |
H16B | 0.002429 | 0.570354 | 0.242627 | 0.070* | |
H16C | −0.055015 | 0.534573 | 0.327545 | 0.070* | |
C17 | 0.27883 (12) | 0.64059 (7) | 0.19723 (12) | 0.0149 (3) | |
C18 | 0.33088 (13) | 0.58220 (7) | 0.15614 (12) | 0.0151 (3) | |
C19 | 0.46066 (13) | 0.55974 (8) | 0.21467 (12) | 0.0171 (3) | |
H19 | 0.515995 | 0.585501 | 0.283915 | 0.021* | |
C20 | 0.50692 (14) | 0.50254 (8) | 0.17387 (13) | 0.0199 (3) | |
H20 | 0.593432 | 0.489206 | 0.215031 | 0.024* | |
C21 | 0.42774 (15) | 0.46271 (8) | 0.07091 (14) | 0.0223 (3) | |
H21 | 0.460922 | 0.422798 | 0.043432 | 0.027* | |
C22 | 0.30435 (14) | 0.48181 (8) | 0.01176 (13) | 0.0206 (3) | |
H22 | 0.251852 | 0.455228 | −0.057734 | 0.025* | |
C23 | 0.25166 (13) | 0.54115 (8) | 0.05188 (12) | 0.0174 (3) | |
C24 | 0.12363 (14) | 0.55804 (8) | −0.00657 (12) | 0.0192 (3) | |
H24 | 0.071627 | 0.530269 | −0.074803 | 0.023* | |
C25 | 0.06980 (13) | 0.61454 (8) | 0.03234 (12) | 0.0178 (3) | |
C26 | 0.14856 (13) | 0.65780 (7) | 0.13450 (12) | 0.0162 (3) | |
C27 | 0.08637 (13) | 0.71596 (8) | 0.16756 (13) | 0.0191 (3) | |
H27 | 0.135306 | 0.747691 | 0.231472 | 0.023* | |
C28 | −0.04097 (14) | 0.72696 (8) | 0.10984 (14) | 0.0220 (3) | |
H28 | −0.078874 | 0.765462 | 0.135365 | 0.026* | |
C29 | −0.11792 (14) | 0.68199 (8) | 0.01238 (14) | 0.0228 (3) | |
H29 | −0.206831 | 0.689377 | −0.025495 | 0.027* | |
C30 | −0.06317 (14) | 0.62827 (8) | −0.02621 (13) | 0.0210 (3) | |
H30 | −0.114157 | 0.599310 | −0.093293 | 0.025* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0196 (5) | 0.0252 (5) | 0.0203 (5) | 0.0012 (4) | 0.0030 (4) | 0.0046 (4) |
O2 | 0.0326 (7) | 0.0324 (6) | 0.0380 (7) | −0.0054 (5) | 0.0184 (6) | 0.0102 (5) |
O3 | 0.0203 (5) | 0.0324 (6) | 0.0278 (6) | −0.0043 (4) | 0.0139 (5) | 0.0013 (5) |
N1 | 0.0150 (6) | 0.0202 (6) | 0.0164 (6) | −0.0014 (5) | 0.0038 (5) | 0.0016 (5) |
C2 | 0.0210 (7) | 0.0160 (6) | 0.0158 (6) | −0.0025 (5) | 0.0074 (6) | −0.0012 (5) |
C3 | 0.0198 (7) | 0.0171 (6) | 0.0147 (6) | −0.0025 (5) | 0.0082 (5) | −0.0011 (5) |
C4 | 0.0146 (6) | 0.0163 (6) | 0.0147 (6) | −0.0009 (5) | 0.0059 (5) | −0.0005 (5) |
C5 | 0.0156 (6) | 0.0164 (6) | 0.0140 (6) | −0.0020 (5) | 0.0065 (5) | −0.0020 (5) |
C6 | 0.0187 (7) | 0.0178 (6) | 0.0135 (6) | −0.0011 (5) | 0.0058 (5) | −0.0016 (5) |
C7 | 0.0231 (7) | 0.0202 (7) | 0.0173 (7) | −0.0036 (6) | 0.0084 (6) | 0.0021 (5) |
C8 | 0.0196 (7) | 0.0222 (7) | 0.0195 (7) | −0.0046 (6) | 0.0099 (6) | −0.0007 (5) |
C9 | 0.0146 (7) | 0.0228 (7) | 0.0179 (7) | −0.0016 (5) | 0.0058 (5) | 0.0004 (5) |
C10 | 0.0169 (7) | 0.0162 (6) | 0.0146 (6) | −0.0012 (5) | 0.0070 (5) | −0.0014 (5) |
C11 | 0.0274 (8) | 0.0308 (8) | 0.0247 (8) | −0.0053 (6) | 0.0156 (7) | −0.0049 (6) |
C12 | 0.0241 (8) | 0.0297 (8) | 0.0277 (8) | −0.0080 (6) | 0.0137 (7) | 0.0003 (6) |
C13 | 0.0268 (8) | 0.0236 (7) | 0.0180 (7) | −0.0033 (6) | 0.0061 (6) | 0.0033 (6) |
C14 | 0.0225 (7) | 0.0266 (7) | 0.0166 (7) | −0.0058 (6) | 0.0092 (6) | −0.0055 (6) |
C15 | 0.0261 (8) | 0.0496 (11) | 0.0316 (9) | −0.0113 (8) | 0.0174 (7) | −0.0048 (8) |
C16 | 0.0397 (11) | 0.0598 (13) | 0.0417 (11) | −0.0258 (10) | 0.0186 (9) | −0.0104 (10) |
C17 | 0.0157 (6) | 0.0156 (6) | 0.0140 (6) | −0.0022 (5) | 0.0067 (5) | 0.0004 (5) |
C18 | 0.0168 (6) | 0.0162 (6) | 0.0141 (6) | −0.0022 (5) | 0.0083 (5) | 0.0013 (5) |
C19 | 0.0172 (7) | 0.0182 (6) | 0.0164 (7) | −0.0014 (5) | 0.0076 (5) | 0.0013 (5) |
C20 | 0.0200 (7) | 0.0205 (7) | 0.0220 (7) | 0.0022 (5) | 0.0115 (6) | 0.0026 (5) |
C21 | 0.0301 (8) | 0.0174 (7) | 0.0253 (8) | 0.0001 (6) | 0.0175 (7) | −0.0008 (6) |
C22 | 0.0260 (8) | 0.0188 (7) | 0.0199 (7) | −0.0070 (6) | 0.0125 (6) | −0.0046 (5) |
C23 | 0.0207 (7) | 0.0170 (6) | 0.0162 (7) | −0.0041 (5) | 0.0094 (6) | 0.0005 (5) |
C24 | 0.0207 (7) | 0.0198 (7) | 0.0152 (6) | −0.0056 (5) | 0.0057 (6) | −0.0006 (5) |
C25 | 0.0166 (7) | 0.0189 (7) | 0.0169 (7) | −0.0043 (5) | 0.0062 (5) | 0.0029 (5) |
C26 | 0.0154 (6) | 0.0170 (6) | 0.0168 (6) | −0.0027 (5) | 0.0074 (5) | 0.0023 (5) |
C27 | 0.0176 (7) | 0.0195 (7) | 0.0209 (7) | −0.0006 (5) | 0.0087 (6) | 0.0014 (5) |
C28 | 0.0193 (7) | 0.0220 (7) | 0.0275 (8) | 0.0017 (6) | 0.0125 (6) | 0.0055 (6) |
C29 | 0.0144 (7) | 0.0262 (7) | 0.0260 (8) | −0.0014 (6) | 0.0067 (6) | 0.0094 (6) |
C30 | 0.0175 (7) | 0.0230 (7) | 0.0193 (7) | −0.0060 (5) | 0.0046 (6) | 0.0041 (6) |
Geometric parameters (Å, º) top
O1—C6 | 1.2370 (17) | C9—C10 | 1.5036 (19) |
O2—C14 | 1.2138 (19) | C15—C16 | 1.510 (3) |
O3—C14 | 1.3489 (19) | C17—C18 | 1.4188 (19) |
O3—C15 | 1.4486 (19) | C17—C26 | 1.4188 (19) |
N1—C2 | 1.3893 (18) | C18—C19 | 1.4342 (19) |
N1—C10 | 1.3658 (18) | C18—C23 | 1.4377 (19) |
C2—C3 | 1.350 (2) | C19—C20 | 1.362 (2) |
C2—C13 | 1.5013 (19) | C20—C21 | 1.416 (2) |
C3—C4 | 1.5275 (18) | C21—C22 | 1.356 (2) |
C3—C14 | 1.4749 (19) | C22—C23 | 1.430 (2) |
C4—C5 | 1.5220 (18) | C23—C24 | 1.391 (2) |
C4—C17 | 1.5413 (18) | C24—C25 | 1.391 (2) |
C5—C6 | 1.4430 (19) | C25—C26 | 1.4417 (19) |
C5—C10 | 1.3550 (19) | C25—C30 | 1.430 (2) |
C6—C7 | 1.5146 (19) | C26—C27 | 1.4356 (19) |
C7—C8 | 1.527 (2) | C27—C28 | 1.364 (2) |
C8—C9 | 1.534 (2) | C28—C29 | 1.419 (2) |
C8—C11 | 1.534 (2) | C29—C30 | 1.358 (2) |
C8—C12 | 1.533 (2) | | |
| | | |
C14—O3—C15 | 116.95 (13) | O2—C14—O3 | 122.01 (14) |
C10—N1—C2 | 122.41 (12) | O2—C14—C3 | 126.59 (14) |
N1—C2—C13 | 112.76 (12) | O3—C14—C3 | 111.41 (12) |
C3—C2—N1 | 119.95 (12) | O3—C15—C16 | 111.51 (14) |
C3—C2—C13 | 127.23 (13) | C18—C17—C4 | 120.66 (12) |
C2—C3—C4 | 122.61 (12) | C18—C17—C26 | 119.36 (12) |
C2—C3—C14 | 119.20 (13) | C26—C17—C4 | 119.90 (12) |
C14—C3—C4 | 117.97 (12) | C17—C18—C19 | 123.51 (12) |
C3—C4—C17 | 112.38 (11) | C17—C18—C23 | 119.94 (12) |
C5—C4—C3 | 110.73 (11) | C19—C18—C23 | 116.53 (12) |
C5—C4—C17 | 114.41 (11) | C20—C19—C18 | 121.93 (13) |
C6—C5—C4 | 118.40 (12) | C19—C20—C21 | 120.87 (14) |
C10—C5—C4 | 122.21 (12) | C22—C21—C20 | 119.68 (13) |
C10—C5—C6 | 118.85 (12) | C21—C22—C23 | 121.31 (13) |
O1—C6—C5 | 121.10 (13) | C22—C23—C18 | 119.67 (13) |
O1—C6—C7 | 119.63 (12) | C24—C23—C18 | 119.61 (13) |
C5—C6—C7 | 119.20 (12) | C24—C23—C22 | 120.69 (13) |
C6—C7—C8 | 115.17 (12) | C25—C24—C23 | 121.68 (13) |
C7—C8—C9 | 107.55 (11) | C24—C25—C26 | 119.48 (13) |
C7—C8—C11 | 110.50 (12) | C24—C25—C30 | 120.32 (13) |
C7—C8—C12 | 109.77 (12) | C30—C25—C26 | 120.17 (13) |
C9—C8—C11 | 110.82 (12) | C17—C26—C25 | 119.88 (12) |
C12—C8—C9 | 108.59 (12) | C17—C26—C27 | 124.04 (13) |
C12—C8—C11 | 109.57 (12) | C27—C26—C25 | 116.07 (12) |
C10—C9—C8 | 112.84 (11) | C28—C27—C26 | 121.87 (14) |
N1—C10—C9 | 115.33 (12) | C27—C28—C29 | 121.26 (14) |
C5—C10—N1 | 120.82 (12) | C30—C29—C28 | 119.33 (13) |
C5—C10—C9 | 123.84 (12) | C29—C30—C25 | 121.17 (14) |
| | | |
O1—C6—C7—C8 | −160.55 (13) | C13—C2—C3—C4 | 175.60 (13) |
N1—C2—C3—C4 | −1.6 (2) | C13—C2—C3—C14 | 1.1 (2) |
N1—C2—C3—C14 | −176.08 (12) | C14—O3—C15—C16 | −82.03 (19) |
C2—N1—C10—C5 | −10.5 (2) | C14—C3—C4—C5 | 167.62 (12) |
C2—N1—C10—C9 | 168.21 (12) | C14—C3—C4—C17 | −63.06 (16) |
C2—C3—C4—C5 | −6.93 (18) | C15—O3—C14—O2 | −7.7 (2) |
C2—C3—C4—C17 | 122.39 (14) | C15—O3—C14—C3 | 172.08 (12) |
C2—C3—C14—O2 | −25.1 (2) | C17—C4—C5—C6 | 67.85 (16) |
C2—C3—C14—O3 | 155.09 (13) | C17—C4—C5—C10 | −120.75 (14) |
C3—C4—C5—C6 | −163.92 (11) | C17—C18—C19—C20 | 178.82 (13) |
C3—C4—C5—C10 | 7.48 (18) | C17—C18—C23—C22 | −179.25 (12) |
C3—C4—C17—C18 | −65.27 (16) | C17—C18—C23—C24 | −1.38 (19) |
C3—C4—C17—C26 | 111.42 (14) | C17—C26—C27—C28 | −175.04 (13) |
C4—C3—C14—O2 | 160.16 (14) | C18—C17—C26—C25 | 1.94 (19) |
C4—C3—C14—O3 | −19.65 (17) | C18—C17—C26—C27 | −179.50 (12) |
C4—C5—C6—O1 | 2.40 (19) | C18—C19—C20—C21 | 0.1 (2) |
C4—C5—C6—C7 | 179.41 (12) | C18—C23—C24—C25 | 0.8 (2) |
C4—C5—C10—N1 | 0.6 (2) | C19—C18—C23—C22 | −0.43 (18) |
C4—C5—C10—C9 | −178.06 (12) | C19—C18—C23—C24 | 177.45 (12) |
C4—C17—C18—C19 | −2.05 (19) | C19—C20—C21—C22 | 0.2 (2) |
C4—C17—C18—C23 | 176.69 (12) | C20—C21—C22—C23 | −0.6 (2) |
C4—C17—C26—C25 | −174.79 (12) | C21—C22—C23—C18 | 0.8 (2) |
C4—C17—C26—C27 | 3.8 (2) | C21—C22—C23—C24 | −177.10 (13) |
C5—C4—C17—C18 | 62.12 (16) | C22—C23—C24—C25 | 178.66 (13) |
C5—C4—C17—C26 | −121.19 (13) | C23—C18—C19—C20 | 0.04 (19) |
C5—C6—C7—C8 | 22.39 (18) | C23—C24—C25—C26 | 1.1 (2) |
C6—C5—C10—N1 | 171.93 (12) | C23—C24—C25—C30 | −177.01 (13) |
C6—C5—C10—C9 | −6.7 (2) | C24—C25—C26—C17 | −2.52 (19) |
C6—C7—C8—C9 | −49.79 (16) | C24—C25—C26—C27 | 178.81 (12) |
C6—C7—C8—C11 | 71.30 (15) | C24—C25—C30—C29 | 178.32 (13) |
C6—C7—C8—C12 | −167.75 (12) | C25—C26—C27—C28 | 3.6 (2) |
C7—C8—C9—C10 | 49.90 (15) | C26—C17—C18—C19 | −178.75 (12) |
C8—C9—C10—N1 | 157.27 (12) | C26—C17—C18—C23 | −0.01 (19) |
C8—C9—C10—C5 | −24.03 (19) | C26—C25—C30—C29 | 0.2 (2) |
C10—N1—C2—C3 | 11.0 (2) | C26—C27—C28—C29 | −1.2 (2) |
C10—N1—C2—C13 | −166.55 (13) | C27—C28—C29—C30 | −1.8 (2) |
C10—C5—C6—O1 | −169.29 (13) | C28—C29—C30—C25 | 2.3 (2) |
C10—C5—C6—C7 | 7.72 (19) | C30—C25—C26—C17 | 175.63 (12) |
C11—C8—C9—C10 | −70.98 (15) | C30—C25—C26—C27 | −3.04 (19) |
C12—C8—C9—C10 | 168.62 (12) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.90 (2) | 1.94 (2) | 2.7776 (16) | 154.2 (18) |
C13—H13B···O2ii | 0.98 | 2.65 | 3.409 (2) | 134 |
C19—H19···N1 | 0.95 | 2.48 | 3.4148 (19) | 168 |
Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) −x+1, −y+1, −z+1. |