Dimethyl 4-[4-(2-meth­oxy-2-oxoeth­oxy)phen­yl]-2,6-dimethyl-1,4-dihydro­pyridine-3,5-dicarboxyl­ate

The 1,4-dihydro­pyridine (1,4-DHP) ring of the title compound, C₂₀H₂₃NO₇, adopts a flattened boat conformation. The carbonyl groups of the ester groups, at positions 3 and 5 in the 1,4-DHP ring, have cis configurations with respect to the double bonds in the 1,4-DHP ring. In the solid state, centrosymmetrically related mol­ecules form dimers through inter­molecular N—H...O hydrogen bonds with a graph-set motif of R₂²(26). Inter­molecular C—H...O inter­actions are also observed.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.051
• wR factor = 0.133
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C20

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

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).

Dimethyl 4-[4-(2-methoxy-2-oxoethoxy)phenyl]-2,6-dimethyl- 1,4-dihydropyridine-3,5-dicarboxylate

Crystal data

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) Å^3	Isomeric, yellow
Z = 8	0.5 × 0.5 × 0.5 mm
F(000) = 1648

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0519P)^2 + 1.4635P] where P = (Fo^2 + 2Fc^2)/3
3888 reflections	(Δ/σ)max < 0.001
262 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6^i	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···O1^ii	0.96	2.59	3.196 (4)	121
C19—H19B···O3^iii	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.