Dimethyl 4-{4-[2-(dimethyl­amino)eth­oxy]phen­yl}-2,6-dimethyl-1,4-dihydro­pyridine-3,5-dicarboxyl­ate

In the mol­ecule of the title compound, C₂₁H₂₈N₂O₅, the substituted 1,4-dihydro­pyridine (1,4-DHP) ring has 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, the mol­ecules are linked by inter­molecular N—H...N hydrogen bonds, which run parallel to the c axis with a graph-set motif C(13). Weak inter- and intra­molecular C—H...O inter­actions are also observed.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.045
• wR factor = 0.136
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



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
   0 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
   0 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

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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-(dimethylamino)ethoxy]phenyl}-2,6-dimethyl-1,4-dihydropyridine- 3,5-dicarboxylate

Crystal data

C21H28N2O5	Z = 2
Mr = 388.45	F(000) = 416
Triclinic, P1	Dx = 1.251 Mg m^−3
Hall symbol: -P 1	Melting point = 412–414 K
a = 8.4072 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.2593 (7) Å	Cell parameters from 5049 reflections
c = 11.5788 (7) Å	θ = 2.4–28.0°
α = 71.036 (1)°	µ = 0.09 mm^−1
β = 86.840 (1)°	T = 293 K
γ = 84.209 (1)°	Block, brown
V = 1030.97 (11) Å^3	0.10 × 0.06 × 0.05 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3131 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.018
Graphite monochromator	θmax = 25.0°, θmin = 1.9°
ω scans	h = −9→9
10002 measured reflections	k = −13→13
3617 independent reflections	l = −13→13

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0785P)^2 + 0.1721P] where P = (Fo^2 + 2Fc^2)/3
3617 reflections	(Δ/σ)max < 0.001
263 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.12 e Å^−3

Special details

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
O1	0.69175 (16)	−0.12265 (12)	0.21621 (13)	0.0762 (4)
O2	0.91882 (14)	−0.15180 (10)	0.31472 (11)	0.0629 (3)
O3	1.35151 (16)	0.25648 (15)	0.07433 (14)	0.0837 (4)
O4	1.29418 (14)	0.12842 (13)	0.25826 (12)	0.0694 (4)
O5	0.67518 (16)	0.34464 (11)	0.53061 (10)	0.0632 (3)
N1	0.88027 (16)	0.21699 (13)	−0.01777 (12)	0.0517 (3)
H1	0.837 (2)	0.2665 (18)	−0.0917 (18)	0.061 (5)*
N2	0.67618 (17)	0.41291 (13)	0.77462 (12)	0.0564 (4)
C2	0.81401 (18)	0.10683 (14)	0.04751 (14)	0.0468 (4)
C3	0.87345 (17)	0.03824 (13)	0.15768 (13)	0.0434 (3)
C4	0.99286 (16)	0.09390 (13)	0.21528 (13)	0.0422 (3)
H4	1.0643	0.0242	0.2655	0.051*
C5	1.09342 (17)	0.17903 (14)	0.11644 (14)	0.0455 (3)
C6	1.02817 (19)	0.24445 (14)	0.00781 (14)	0.0487 (4)
C7	0.90586 (16)	0.16122 (13)	0.29913 (13)	0.0416 (3)
C8	0.87713 (19)	0.29149 (14)	0.26544 (14)	0.0522 (4)
H8	0.9109	0.3407	0.1884	0.063*
C9	0.7998 (2)	0.34954 (15)	0.34345 (15)	0.0562 (4)
H9	0.7829	0.4370	0.3188	0.067*
C10	0.74708 (18)	0.27879 (15)	0.45791 (13)	0.0486 (4)
C11	0.77129 (19)	0.14873 (15)	0.49254 (14)	0.0505 (4)
H11	0.7348	0.0997	0.5687	0.061*
C12	0.84973 (19)	0.09217 (14)	0.41377 (14)	0.0487 (4)
H12	0.8656	0.0047	0.4383	0.058*
C13	0.6843 (2)	0.07438 (17)	−0.01724 (16)	0.0610 (4)
H13A	0.5889	0.1282	−0.0150	0.091*
H13B	0.6635	−0.0120	0.0223	0.091*
H13C	0.7173	0.0861	−0.1006	0.091*
C14	0.81540 (18)	−0.08316 (14)	0.22814 (14)	0.0490 (4)
C15	0.8642 (3)	−0.26413 (19)	0.4012 (2)	0.0820 (6)
H15A	0.8503	−0.3239	0.3602	0.123*
H15B	0.7641	−0.2438	0.4374	0.123*
H15C	0.9418	−0.2998	0.4637	0.123*
C16	1.0990 (2)	0.34761 (18)	−0.09291 (17)	0.0673 (5)
H16A	1.1876	0.3124	−0.1307	0.101*
H16B	1.1353	0.4078	−0.0599	0.101*
H16C	1.0193	0.3888	−0.1527	0.101*
C17	1.25693 (18)	0.19485 (15)	0.14355 (16)	0.0524 (4)
C18	1.4536 (2)	0.1344 (2)	0.2943 (2)	0.0866 (7)
H18A	1.4783	0.2207	0.2686	0.130*
H18B	1.5286	0.0871	0.2568	0.130*
H18C	1.4601	0.0994	0.3815	0.130*
C19	0.6325 (2)	0.27291 (17)	0.65256 (14)	0.0564 (4)
H19A	0.7268	0.2245	0.6941	0.068*
H19B	0.5563	0.2143	0.6509	0.068*
C20	0.5601 (2)	0.35893 (17)	0.72079 (15)	0.0571 (4)
H20A	0.4946	0.4273	0.6653	0.069*
H20B	0.4902	0.3122	0.7855	0.069*
C21	0.7526 (3)	0.5121 (2)	0.68121 (19)	0.0786 (6)
H21A	0.8217	0.5507	0.7191	0.118*
H21B	0.6723	0.5745	0.6367	0.118*
H21C	0.8143	0.4767	0.6262	0.118*
C22	0.5953 (3)	0.4641 (2)	0.86498 (19)	0.0787 (6)
H22A	0.5137	0.5286	0.8262	0.118*
H22B	0.6714	0.4994	0.9004	0.118*
H22C	0.5475	0.3980	0.9279	0.118*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0717 (8)	0.0667 (8)	0.0823 (9)	−0.0343 (7)	−0.0125 (7)	−0.0030 (7)
O2	0.0659 (7)	0.0468 (6)	0.0654 (7)	−0.0160 (5)	−0.0103 (6)	0.0012 (5)
O3	0.0609 (8)	0.0937 (10)	0.0896 (10)	−0.0381 (7)	0.0093 (7)	−0.0125 (8)
O4	0.0469 (7)	0.0762 (8)	0.0777 (9)	−0.0177 (6)	−0.0119 (6)	−0.0093 (7)
O5	0.0833 (8)	0.0575 (7)	0.0449 (6)	0.0015 (6)	0.0073 (6)	−0.0149 (5)
N1	0.0568 (8)	0.0493 (7)	0.0438 (7)	−0.0110 (6)	−0.0044 (6)	−0.0054 (6)
N2	0.0628 (8)	0.0563 (8)	0.0507 (8)	−0.0129 (6)	0.0054 (6)	−0.0168 (6)
C2	0.0482 (8)	0.0459 (8)	0.0473 (8)	−0.0087 (6)	0.0018 (6)	−0.0155 (7)
C3	0.0425 (8)	0.0423 (8)	0.0458 (8)	−0.0082 (6)	0.0026 (6)	−0.0140 (6)
C4	0.0403 (7)	0.0393 (7)	0.0445 (8)	−0.0070 (6)	−0.0012 (6)	−0.0089 (6)
C5	0.0424 (8)	0.0433 (8)	0.0513 (9)	−0.0083 (6)	0.0056 (6)	−0.0156 (7)
C6	0.0529 (9)	0.0446 (8)	0.0485 (9)	−0.0107 (6)	0.0090 (7)	−0.0145 (7)
C7	0.0389 (7)	0.0439 (7)	0.0403 (7)	−0.0091 (6)	−0.0048 (6)	−0.0090 (6)
C8	0.0631 (10)	0.0449 (8)	0.0424 (8)	−0.0065 (7)	0.0064 (7)	−0.0064 (6)
C9	0.0700 (10)	0.0428 (8)	0.0498 (9)	−0.0015 (7)	0.0038 (8)	−0.0087 (7)
C10	0.0504 (8)	0.0533 (9)	0.0416 (8)	−0.0031 (7)	−0.0027 (6)	−0.0150 (7)
C11	0.0588 (9)	0.0519 (9)	0.0374 (7)	−0.0112 (7)	0.0007 (7)	−0.0079 (6)
C12	0.0562 (9)	0.0424 (8)	0.0450 (8)	−0.0085 (6)	−0.0036 (7)	−0.0090 (6)
C13	0.0667 (11)	0.0611 (10)	0.0555 (10)	−0.0158 (8)	−0.0119 (8)	−0.0148 (8)
C14	0.0503 (9)	0.0472 (8)	0.0508 (9)	−0.0110 (7)	0.0010 (7)	−0.0160 (7)
C15	0.0986 (15)	0.0578 (11)	0.0738 (13)	−0.0294 (10)	−0.0110 (11)	0.0087 (10)
C16	0.0753 (12)	0.0615 (10)	0.0564 (10)	−0.0210 (9)	0.0109 (9)	−0.0047 (8)
C17	0.0458 (8)	0.0480 (8)	0.0656 (10)	−0.0121 (7)	0.0064 (7)	−0.0200 (8)
C18	0.0527 (11)	0.0894 (15)	0.1132 (18)	−0.0164 (10)	−0.0255 (11)	−0.0194 (13)
C19	0.0606 (10)	0.0617 (10)	0.0472 (9)	−0.0137 (8)	0.0083 (7)	−0.0170 (8)
C20	0.0535 (9)	0.0650 (10)	0.0523 (9)	−0.0078 (8)	0.0078 (7)	−0.0190 (8)
C21	0.0868 (14)	0.0739 (12)	0.0707 (12)	−0.0291 (11)	0.0080 (10)	−0.0124 (10)
C22	0.1024 (16)	0.0699 (12)	0.0710 (13)	−0.0105 (11)	0.0119 (11)	−0.0339 (10)

Geometric parameters (Å, º)

O1—C14	1.2028 (19)	C9—H9	0.9300
O2—C14	1.3473 (19)	C10—C11	1.383 (2)
O2—C15	1.434 (2)	C11—C12	1.378 (2)
O3—C17	1.198 (2)	C11—H11	0.9300
O4—C17	1.332 (2)	C12—H12	0.9300
O4—C18	1.440 (2)	C13—H13A	0.9600
O5—C10	1.3722 (19)	C13—H13B	0.9600
O5—C19	1.4271 (19)	C13—H13C	0.9600
N1—C2	1.380 (2)	C15—H15A	0.9600
N1—C6	1.381 (2)	C15—H15B	0.9600
N1—H1	0.93 (2)	C15—H15C	0.9600
N2—C21	1.454 (2)	C16—H16A	0.9600
N2—C22	1.457 (2)	C16—H16B	0.9600
N2—C20	1.464 (2)	C16—H16C	0.9600
C2—C3	1.351 (2)	C18—H18A	0.9600
C2—C13	1.494 (2)	C18—H18B	0.9600
C3—C14	1.462 (2)	C18—H18C	0.9600
C3—C4	1.5224 (19)	C19—C20	1.503 (2)
C4—C5	1.5124 (19)	C19—H19A	0.9700
C4—C7	1.530 (2)	C19—H19B	0.9700
C4—H4	0.9800	C20—H20A	0.9700
C5—C6	1.348 (2)	C20—H20B	0.9700
C5—C17	1.467 (2)	C21—H21A	0.9600
C6—C16	1.499 (2)	C21—H21B	0.9600
C7—C12	1.387 (2)	C21—H21C	0.9600
C7—C8	1.389 (2)	C22—H22A	0.9600
C8—C9	1.378 (2)	C22—H22B	0.9600
C8—H8	0.9300	C22—H22C	0.9600
C9—C10	1.381 (2)
C14—O2—C15	116.63 (14)	H13B—C13—H13C	109.5
C17—O4—C18	116.56 (15)	O1—C14—O2	120.85 (14)
C10—O5—C19	116.86 (12)	O1—C14—C3	127.40 (15)
C2—N1—C6	122.58 (13)	O2—C14—C3	111.75 (13)
C2—N1—H1	119.4 (11)	O2—C15—H15A	109.5
C6—N1—H1	116.6 (11)	O2—C15—H15B	109.5
C21—N2—C22	109.56 (15)	H15A—C15—H15B	109.5
C21—N2—C20	110.87 (14)	O2—C15—H15C	109.5
C22—N2—C20	109.43 (14)	H15A—C15—H15C	109.5
C3—C2—N1	118.95 (13)	H15B—C15—H15C	109.5
C3—C2—C13	126.94 (14)	C6—C16—H16A	109.5
N1—C2—C13	114.07 (13)	C6—C16—H16B	109.5
C2—C3—C14	121.71 (13)	H16A—C16—H16B	109.5
C2—C3—C4	119.19 (12)	C6—C16—H16C	109.5
C14—C3—C4	118.87 (13)	H16A—C16—H16C	109.5
C5—C4—C3	109.78 (12)	H16B—C16—H16C	109.5
C5—C4—C7	112.81 (11)	O3—C17—O4	121.50 (16)
C3—C4—C7	110.29 (11)	O3—C17—C5	126.79 (17)
C5—C4—H4	107.9	O4—C17—C5	111.70 (13)
C3—C4—H4	107.9	O4—C18—H18A	109.5
C7—C4—H4	107.9	O4—C18—H18B	109.5
C6—C5—C17	121.30 (14)	H18A—C18—H18B	109.5
C6—C5—C4	119.43 (13)	O4—C18—H18C	109.5
C17—C5—C4	119.15 (13)	H18A—C18—H18C	109.5
C5—C6—N1	118.98 (14)	H18B—C18—H18C	109.5
C5—C6—C16	126.99 (15)	O5—C19—C20	110.20 (14)
N1—C6—C16	114.02 (14)	O5—C19—H19A	109.6
C12—C7—C8	116.89 (14)	C20—C19—H19A	109.6
C12—C7—C4	120.25 (13)	O5—C19—H19B	109.6
C8—C7—C4	122.85 (13)	C20—C19—H19B	109.6
C9—C8—C7	121.53 (14)	H19A—C19—H19B	108.1
C9—C8—H8	119.2	N2—C20—C19	114.70 (14)
C7—C8—H8	119.2	N2—C20—H20A	108.6
C8—C9—C10	120.49 (15)	C19—C20—H20A	108.6
C8—C9—H9	119.8	N2—C20—H20B	108.6
C10—C9—H9	119.8	C19—C20—H20B	108.6
O5—C10—C9	116.47 (14)	H20A—C20—H20B	107.6
O5—C10—C11	124.48 (14)	N2—C21—H21A	109.5
C9—C10—C11	119.04 (14)	N2—C21—H21B	109.5
C12—C11—C10	119.75 (14)	H21A—C21—H21B	109.5
C12—C11—H11	120.1	N2—C21—H21C	109.5
C10—C11—H11	120.1	H21A—C21—H21C	109.5
C11—C12—C7	122.28 (14)	H21B—C21—H21C	109.5
C11—C12—H12	118.9	N2—C22—H22A	109.5
C7—C12—H12	118.9	N2—C22—H22B	109.5
C2—C13—H13A	109.5	H22A—C22—H22B	109.5
C2—C13—H13B	109.5	N2—C22—H22C	109.5
H13A—C13—H13B	109.5	H22A—C22—H22C	109.5
C2—C13—H13C	109.5	H22B—C22—H22C	109.5
H13A—C13—H13C	109.5
C6—N1—C2—C3	17.1 (2)	C7—C8—C9—C10	−0.6 (3)
C6—N1—C2—C13	−160.55 (14)	C19—O5—C10—C9	−174.91 (14)
N1—C2—C3—C14	−176.18 (13)	C19—O5—C10—C11	4.1 (2)
C13—C2—C3—C14	1.2 (2)	C8—C9—C10—O5	178.30 (15)
N1—C2—C3—C4	9.5 (2)	C8—C9—C10—C11	−0.8 (3)
C13—C2—C3—C4	−173.17 (14)	O5—C10—C11—C12	−177.82 (14)
C2—C3—C4—C5	−32.22 (18)	C9—C10—C11—C12	1.2 (2)
C14—C3—C4—C5	153.27 (13)	C10—C11—C12—C7	−0.3 (2)
C2—C3—C4—C7	92.68 (15)	C8—C7—C12—C11	−1.1 (2)
C14—C3—C4—C7	−81.82 (16)	C4—C7—C12—C11	179.74 (13)
C3—C4—C5—C6	32.71 (18)	C15—O2—C14—O1	−8.4 (2)
C7—C4—C5—C6	−90.73 (16)	C15—O2—C14—C3	170.99 (16)
C3—C4—C5—C17	−151.16 (13)	C2—C3—C14—O1	−18.9 (3)
C7—C4—C5—C17	85.40 (16)	C4—C3—C14—O1	155.45 (16)
C17—C5—C6—N1	173.55 (13)	C2—C3—C14—O2	161.70 (14)
C4—C5—C6—N1	−10.4 (2)	C4—C3—C14—O2	−23.94 (19)
C17—C5—C6—C16	−6.5 (3)	C18—O4—C17—O3	−0.1 (3)
C4—C5—C6—C16	169.57 (15)	C18—O4—C17—C5	178.56 (16)
C2—N1—C6—C5	−16.7 (2)	C6—C5—C17—O3	−5.7 (3)
C2—N1—C6—C16	163.28 (15)	C4—C5—C17—O3	178.23 (16)
C5—C4—C7—C12	−160.20 (13)	C6—C5—C17—O4	175.68 (14)
C3—C4—C7—C12	76.65 (16)	C4—C5—C17—O4	−0.4 (2)
C5—C4—C7—C8	20.67 (19)	C10—O5—C19—C20	178.26 (13)
C3—C4—C7—C8	−102.48 (16)	C21—N2—C20—C19	74.88 (19)
C12—C7—C8—C9	1.5 (2)	C22—N2—C20—C19	−164.16 (15)
C4—C7—C8—C9	−179.35 (14)	O5—C19—C20—N2	−84.02 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2^i	0.93 (2)	2.25 (2)	3.136 (2)	159.7 (15)
C4—H4···O2	0.98	2.33	2.7503 (18)	105
C13—H13B···O1	0.96	2.20	2.885 (2)	128
C21—H21C···O5	0.96	2.52	3.087 (3)	118
C22—H22C···O3^ii	0.96	2.57	3.504 (3)	165

Symmetry codes: (i) x, y, z−1; (ii) x−1, y, z+1.