Dimethyl 4-[4-(2-methoxy-2-oxoethoxy)phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680604089X/bt2190sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680604089X/bt2190Isup2.hkl |
CCDC reference: 627333
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
C20H23NO7 | Dx = 1.305 Mg m−3 |
Mr = 389.39 | Melting point = 412–414 K |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 12929 reflections |
a = 14.4587 (12) Å | θ = 2.9–26.0° |
b = 14.4275 (10) Å | µ = 0.1 mm−1 |
c = 19.0072 (13) Å | T = 293 K |
V = 3965.0 (5) Å3 | Isomeric, yellow |
Z = 8 | 0.5 × 0.5 × 0.5 mm |
F(000) = 1648 |
Oxford Gemini S CCD area-detector diffractometer | 3888 independent reflections |
Radiation source: fine-focus sealed tube | 3024 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
ω scans | θmax = 26.0°, θmin = 2.9° |
Absorption correction: multi-scan (ABSPACK in CrysAlis RED; Oxford Diffraction, 2006) | h = −17→17 |
Tmin = 0.873, Tmax = 0.950 | k = −17→17 |
35852 measured reflections | l = −23→23 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.133 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0519P)2 + 1.4635P] where P = (Fo2 + 2Fc2)/3 |
3888 reflections | (Δ/σ)max < 0.001 |
262 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
Experimental. CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.30.5 (release 12–06-2006 CrysAlis 171. NET) (compiled Jun 12 2006,17:01:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
N1 | −0.17295 (13) | 0.60961 (13) | 0.62388 (10) | 0.0590 (5) | |
H1 | −0.1923 (17) | 0.5687 (18) | 0.6481 (13) | 0.074 (8)* | |
C2 | −0.22259 (13) | 0.62733 (14) | 0.56322 (11) | 0.0532 (5) | |
C3 | −0.19814 (12) | 0.69971 (13) | 0.52279 (10) | 0.0485 (5) | |
C4 | −0.10975 (12) | 0.75370 (12) | 0.53804 (9) | 0.0439 (4) | |
H4 | −0.1212 | 0.8193 | 0.5280 | 0.053* | |
C5 | −0.08275 (13) | 0.74460 (13) | 0.61507 (10) | 0.0476 (4) | |
C6 | −0.11011 (14) | 0.67034 (14) | 0.65272 (10) | 0.0537 (5) | |
C7 | −0.03165 (12) | 0.72007 (12) | 0.49022 (9) | 0.0407 (4) | |
C8 | 0.01111 (13) | 0.63586 (14) | 0.50228 (10) | 0.0497 (5) | |
H8 | −0.0065 | 0.6009 | 0.5411 | 0.060* | |
C9 | 0.07897 (14) | 0.60230 (14) | 0.45844 (10) | 0.0546 (5) | |
H9 | 0.1068 | 0.5456 | 0.4681 | 0.065* | |
C10 | 0.10568 (12) | 0.65265 (13) | 0.40029 (10) | 0.0468 (4) | |
C11 | 0.06575 (14) | 0.73728 (14) | 0.38745 (10) | 0.0539 (5) | |
H11 | 0.0844 | 0.7726 | 0.3490 | 0.065* | |
C12 | −0.00284 (13) | 0.76970 (13) | 0.43251 (11) | 0.0520 (5) | |
H12 | −0.0301 | 0.8268 | 0.4233 | 0.062* | |
C13 | −0.30127 (15) | 0.56111 (16) | 0.55133 (15) | 0.0747 (7) | |
H13A | −0.3514 | 0.5931 | 0.5288 | 0.112* | |
H13B | −0.3218 | 0.5369 | 0.5957 | 0.112* | |
H13C | −0.2809 | 0.5111 | 0.5219 | 0.112* | |
C14 | −0.25239 (14) | 0.72532 (16) | 0.46063 (11) | 0.0592 (5) | |
O1 | −0.31089 (14) | 0.67988 (15) | 0.43247 (11) | 0.1018 (7) | |
O2 | −0.22928 (10) | 0.80900 (11) | 0.43621 (8) | 0.0705 (4) | |
C15 | −0.2793 (2) | 0.8401 (2) | 0.37484 (14) | 0.0937 (9) | |
H15A | −0.2718 | 0.7959 | 0.3375 | 0.141* | |
H15B | −0.2556 | 0.8992 | 0.3601 | 0.141* | |
H15C | −0.3437 | 0.8460 | 0.3861 | 0.141* | |
C16 | −0.0798 (2) | 0.64489 (19) | 0.72585 (12) | 0.0784 (7) | |
H16A | −0.0152 | 0.6294 | 0.7255 | 0.118* | |
H16B | −0.1149 | 0.5926 | 0.7420 | 0.118* | |
H16C | −0.0899 | 0.6965 | 0.7568 | 0.118* | |
C17 | −0.02285 (14) | 0.81561 (16) | 0.64571 (12) | 0.0580 (5) | |
O3 | 0.01710 (13) | 0.81221 (15) | 0.70135 (9) | 0.0916 (6) | |
O4 | −0.01618 (11) | 0.88990 (10) | 0.60347 (9) | 0.0738 (5) | |
C18 | 0.0413 (2) | 0.96458 (18) | 0.62757 (19) | 0.1000 (10) | |
H18A | 0.0117 | 0.9954 | 0.6662 | 0.150* | |
H18B | 0.0508 | 1.0079 | 0.5899 | 0.150* | |
H18C | 0.0999 | 0.9404 | 0.6427 | 0.150* | |
O5 | 0.17178 (10) | 0.61088 (10) | 0.35895 (7) | 0.0654 (4) | |
C19 | 0.20434 (14) | 0.65893 (15) | 0.29970 (10) | 0.0539 (5) | |
H19A | 0.2376 | 0.7142 | 0.3140 | 0.065* | |
H19B | 0.1530 | 0.6773 | 0.2699 | 0.065* | |
C20 | 0.26737 (14) | 0.59474 (15) | 0.26075 (10) | 0.0560 (5) | |
O6 | 0.27135 (16) | 0.51311 (12) | 0.26882 (10) | 0.1018 (7) | |
O7 | 0.31653 (11) | 0.64013 (11) | 0.21426 (8) | 0.0714 (5) | |
C21 | 0.37811 (19) | 0.58671 (19) | 0.17019 (14) | 0.0876 (8) | |
H21A | 0.4124 | 0.5439 | 0.1988 | 0.131* | |
H21B | 0.4202 | 0.6277 | 0.1466 | 0.131* | |
H21C | 0.3426 | 0.5530 | 0.1360 | 0.131* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0626 (11) | 0.0509 (10) | 0.0637 (11) | 0.0027 (9) | 0.0102 (9) | 0.0130 (9) |
C2 | 0.0419 (10) | 0.0508 (11) | 0.0668 (13) | 0.0049 (8) | 0.0076 (9) | −0.0024 (10) |
C3 | 0.0385 (10) | 0.0505 (11) | 0.0564 (11) | 0.0047 (8) | 0.0018 (8) | −0.0013 (9) |
C4 | 0.0451 (10) | 0.0377 (9) | 0.0489 (10) | 0.0038 (8) | 0.0017 (8) | −0.0006 (8) |
C5 | 0.0460 (10) | 0.0510 (11) | 0.0459 (10) | 0.0085 (8) | 0.0043 (8) | −0.0053 (8) |
C6 | 0.0555 (12) | 0.0566 (12) | 0.0490 (11) | 0.0116 (10) | 0.0078 (9) | −0.0019 (9) |
C7 | 0.0388 (9) | 0.0402 (9) | 0.0431 (9) | −0.0041 (7) | −0.0022 (7) | −0.0013 (7) |
C8 | 0.0536 (11) | 0.0517 (11) | 0.0438 (10) | 0.0071 (9) | 0.0077 (8) | 0.0100 (8) |
C9 | 0.0603 (12) | 0.0526 (11) | 0.0508 (11) | 0.0131 (9) | 0.0076 (9) | 0.0076 (9) |
C10 | 0.0422 (10) | 0.0521 (11) | 0.0461 (10) | −0.0008 (8) | 0.0029 (8) | −0.0002 (8) |
C11 | 0.0556 (11) | 0.0509 (11) | 0.0552 (11) | −0.0074 (9) | 0.0097 (9) | 0.0125 (9) |
C12 | 0.0527 (11) | 0.0399 (10) | 0.0634 (12) | 0.0004 (8) | 0.0060 (10) | 0.0081 (9) |
C13 | 0.0542 (13) | 0.0632 (14) | 0.1066 (19) | −0.0095 (11) | 0.0071 (13) | 0.0049 (13) |
C14 | 0.0421 (11) | 0.0728 (15) | 0.0627 (13) | 0.0032 (10) | 0.0006 (10) | 0.0031 (11) |
O1 | 0.0830 (12) | 0.1213 (16) | 0.1009 (14) | −0.0296 (12) | −0.0383 (11) | 0.0180 (12) |
O2 | 0.0624 (9) | 0.0761 (11) | 0.0732 (10) | 0.0091 (8) | −0.0073 (8) | 0.0188 (8) |
C15 | 0.0859 (19) | 0.116 (2) | 0.0790 (17) | 0.0253 (17) | −0.0100 (14) | 0.0328 (16) |
C16 | 0.0936 (18) | 0.0880 (17) | 0.0536 (13) | 0.0114 (14) | 0.0019 (12) | 0.0124 (12) |
C17 | 0.0497 (11) | 0.0688 (14) | 0.0554 (12) | 0.0045 (10) | 0.0047 (10) | −0.0170 (11) |
O3 | 0.0871 (12) | 0.1310 (17) | 0.0567 (10) | −0.0258 (11) | −0.0117 (9) | −0.0127 (10) |
O4 | 0.0735 (10) | 0.0485 (9) | 0.0994 (12) | −0.0028 (7) | −0.0194 (9) | −0.0106 (8) |
C18 | 0.092 (2) | 0.0614 (15) | 0.147 (3) | −0.0135 (14) | −0.0185 (19) | −0.0289 (17) |
O5 | 0.0699 (9) | 0.0678 (9) | 0.0584 (9) | 0.0141 (7) | 0.0254 (7) | 0.0143 (7) |
C19 | 0.0487 (11) | 0.0620 (12) | 0.0511 (11) | −0.0111 (9) | 0.0068 (9) | 0.0028 (9) |
C20 | 0.0583 (12) | 0.0612 (13) | 0.0486 (11) | −0.0130 (10) | 0.0093 (9) | 0.0010 (9) |
O6 | 0.1421 (18) | 0.0618 (11) | 0.1014 (14) | 0.0012 (11) | 0.0709 (13) | 0.0084 (9) |
O7 | 0.0721 (10) | 0.0701 (10) | 0.0720 (10) | −0.0130 (8) | 0.0297 (8) | 0.0044 (8) |
C21 | 0.0908 (18) | 0.0910 (18) | 0.0809 (17) | −0.0118 (15) | 0.0459 (15) | −0.0067 (14) |
N1—C6 | 1.376 (3) | C13—H13C | 0.9600 |
N1—C2 | 1.382 (3) | C14—O1 | 1.197 (3) |
N1—H1 | 0.80 (3) | C14—O2 | 1.336 (3) |
C2—C3 | 1.344 (3) | O2—C15 | 1.444 (3) |
C2—C13 | 1.503 (3) | C15—H15A | 0.9600 |
C3—C14 | 1.466 (3) | C15—H15B | 0.9600 |
C3—C4 | 1.524 (3) | C15—H15C | 0.9600 |
C4—C5 | 1.521 (3) | C16—H16A | 0.9600 |
C4—C7 | 1.529 (2) | C16—H16B | 0.9600 |
C4—H4 | 0.9800 | C16—H16C | 0.9600 |
C5—C6 | 1.348 (3) | C17—O3 | 1.206 (3) |
C5—C17 | 1.462 (3) | C17—O4 | 1.343 (3) |
C6—C16 | 1.503 (3) | O4—C18 | 1.436 (3) |
C7—C12 | 1.375 (3) | C18—H18A | 0.9600 |
C7—C8 | 1.382 (3) | C18—H18B | 0.9600 |
C8—C9 | 1.375 (3) | C18—H18C | 0.9600 |
C8—H8 | 0.9300 | O5—C19 | 1.404 (2) |
C9—C10 | 1.378 (3) | C19—C20 | 1.495 (3) |
C9—H9 | 0.9300 | C19—H19A | 0.9700 |
C10—C11 | 1.372 (3) | C19—H19B | 0.9700 |
C10—O5 | 1.376 (2) | C20—O6 | 1.189 (3) |
C11—C12 | 1.391 (3) | C20—O7 | 1.310 (2) |
C11—H11 | 0.9300 | O7—C21 | 1.445 (3) |
C12—H12 | 0.9300 | C21—H21A | 0.9600 |
C13—H13A | 0.9600 | C21—H21B | 0.9600 |
C13—H13B | 0.9600 | C21—H21C | 0.9600 |
C6—N1—C2 | 123.87 (18) | H13B—C13—H13C | 109.5 |
C6—N1—H1 | 118.2 (18) | O1—C14—O2 | 121.1 (2) |
C2—N1—H1 | 115.8 (18) | O1—C14—C3 | 126.9 (2) |
C3—C2—N1 | 118.96 (19) | O2—C14—C3 | 111.97 (19) |
C3—C2—C13 | 127.4 (2) | C14—O2—C15 | 115.9 (2) |
N1—C2—C13 | 113.64 (19) | O2—C15—H15A | 109.5 |
C2—C3—C14 | 121.07 (18) | O2—C15—H15B | 109.5 |
C2—C3—C4 | 120.59 (17) | H15A—C15—H15B | 109.5 |
C14—C3—C4 | 118.24 (17) | O2—C15—H15C | 109.5 |
C5—C4—C3 | 110.74 (15) | H15A—C15—H15C | 109.5 |
C5—C4—C7 | 110.82 (14) | H15B—C15—H15C | 109.5 |
C3—C4—C7 | 110.13 (14) | C6—C16—H16A | 109.5 |
C5—C4—H4 | 108.4 | C6—C16—H16B | 109.5 |
C3—C4—H4 | 108.4 | H16A—C16—H16B | 109.5 |
C7—C4—H4 | 108.4 | C6—C16—H16C | 109.5 |
C6—C5—C17 | 121.28 (19) | H16A—C16—H16C | 109.5 |
C6—C5—C4 | 120.29 (17) | H16B—C16—H16C | 109.5 |
C17—C5—C4 | 118.35 (17) | O3—C17—O4 | 121.5 (2) |
C5—C6—N1 | 119.24 (19) | O3—C17—C5 | 127.2 (2) |
C5—C6—C16 | 126.8 (2) | O4—C17—C5 | 111.32 (18) |
N1—C6—C16 | 113.91 (19) | C17—O4—C18 | 116.7 (2) |
C12—C7—C8 | 117.05 (16) | O4—C18—H18A | 109.5 |
C12—C7—C4 | 122.21 (16) | O4—C18—H18B | 109.5 |
C8—C7—C4 | 120.71 (16) | H18A—C18—H18B | 109.5 |
C9—C8—C7 | 121.87 (17) | O4—C18—H18C | 109.5 |
C9—C8—H8 | 119.1 | H18A—C18—H18C | 109.5 |
C7—C8—H8 | 119.1 | H18B—C18—H18C | 109.5 |
C8—C9—C10 | 120.02 (18) | C10—O5—C19 | 118.34 (15) |
C8—C9—H9 | 120.0 | O5—C19—C20 | 107.20 (17) |
C10—C9—H9 | 120.0 | O5—C19—H19A | 110.3 |
C11—C10—O5 | 125.45 (17) | C20—C19—H19A | 110.3 |
C11—C10—C9 | 119.60 (17) | O5—C19—H19B | 110.3 |
O5—C10—C9 | 114.95 (17) | C20—C19—H19B | 110.3 |
C10—C11—C12 | 119.30 (17) | H19A—C19—H19B | 108.5 |
C10—C11—H11 | 120.4 | O6—C20—O7 | 123.8 (2) |
C12—C11—H11 | 120.4 | O6—C20—C19 | 125.38 (19) |
C7—C12—C11 | 122.15 (18) | O7—C20—C19 | 110.80 (19) |
C7—C12—H12 | 118.9 | C20—O7—C21 | 117.30 (18) |
C11—C12—H12 | 118.9 | O7—C21—H21A | 109.5 |
C2—C13—H13A | 109.5 | O7—C21—H21B | 109.5 |
C2—C13—H13B | 109.5 | H21A—C21—H21B | 109.5 |
H13A—C13—H13B | 109.5 | O7—C21—H21C | 109.5 |
C2—C13—H13C | 109.5 | H21A—C21—H21C | 109.5 |
H13A—C13—H13C | 109.5 | H21B—C21—H21C | 109.5 |
C6—N1—C2—C3 | 12.0 (3) | C8—C9—C10—C11 | 1.6 (3) |
C6—N1—C2—C13 | −167.00 (19) | C8—C9—C10—O5 | −177.86 (18) |
N1—C2—C3—C14 | −175.71 (18) | O5—C10—C11—C12 | 177.71 (18) |
C13—C2—C3—C14 | 3.1 (3) | C9—C10—C11—C12 | −1.6 (3) |
N1—C2—C3—C4 | 8.0 (3) | C8—C7—C12—C11 | 0.4 (3) |
C13—C2—C3—C4 | −173.17 (19) | C4—C7—C12—C11 | −177.41 (17) |
C2—C3—C4—C5 | −24.9 (2) | C10—C11—C12—C7 | 0.6 (3) |
C14—C3—C4—C5 | 158.71 (17) | C2—C3—C14—O1 | −13.4 (3) |
C2—C3—C4—C7 | 98.0 (2) | C4—C3—C14—O1 | 163.0 (2) |
C14—C3—C4—C7 | −78.4 (2) | C2—C3—C14—O2 | 166.90 (18) |
C3—C4—C5—C6 | 25.3 (2) | C4—C3—C14—O2 | −16.7 (3) |
C7—C4—C5—C6 | −97.2 (2) | O1—C14—O2—C15 | 0.3 (3) |
C3—C4—C5—C17 | −157.79 (16) | C3—C14—O2—C15 | 179.98 (19) |
C7—C4—C5—C17 | 79.69 (19) | C6—C5—C17—O3 | 9.7 (3) |
C17—C5—C6—N1 | 174.28 (17) | C4—C5—C17—O3 | −167.1 (2) |
C4—C5—C6—N1 | −8.9 (3) | C6—C5—C17—O4 | −170.14 (18) |
C17—C5—C6—C16 | −5.1 (3) | C4—C5—C17—O4 | 13.0 (2) |
C4—C5—C6—C16 | 171.69 (19) | O3—C17—O4—C18 | 0.5 (3) |
C2—N1—C6—C5 | −11.5 (3) | C5—C17—O4—C18 | −179.68 (19) |
C2—N1—C6—C16 | 167.95 (19) | C11—C10—O5—C19 | 2.2 (3) |
C5—C4—C7—C12 | −133.65 (18) | C9—C10—O5—C19 | −178.38 (18) |
C3—C4—C7—C12 | 103.5 (2) | C10—O5—C19—C20 | −174.33 (16) |
C5—C4—C7—C8 | 48.6 (2) | O5—C19—C20—O6 | 16.3 (3) |
C3—C4—C7—C8 | −74.3 (2) | O5—C19—C20—O7 | −165.69 (17) |
C12—C7—C8—C9 | −0.5 (3) | O6—C20—O7—C21 | 0.7 (3) |
C4—C7—C8—C9 | 177.35 (18) | C19—C20—O7—C21 | −177.4 (2) |
C7—C8—C9—C10 | −0.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O6i | 0.80 (3) | 2.28 (3) | 3.053 (3) | 163 (2) |
C4—H4···O2 | 0.98 | 2.35 | 2.715 (2) | 101 |
C4—H4···O4 | 0.98 | 2.32 | 2.690 (2) | 101 |
C13—H13A···O1 | 0.96 | 2.29 | 2.839 (3) | 115 |
C18—H18C···O1ii | 0.96 | 2.59 | 3.196 (4) | 121 |
C19—H19B···O3iii | 0.97 | 2.36 | 3.316 (3) | 167 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x+1/2, −y+3/2, −z+1; (iii) x, −y+3/2, z−1/2. |