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

In the title compound, C₂₄H₂₃NO₆, the substituted 1,4-dihydro­pyridine (1,4-DHP) ring has a flat-boat conformation. The carbonyl groups of the ester groups, at positions 3 and 5 of the 1,4-DHP ring, have cis,cis conformations with respect to the double bonds in the 1,4-DHP ring. In the solid state, the mol­ecules are linked by inter­molecular N—H...O and weak inter­molecular C—H...O inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.050
• wR factor = 0.134
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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 2,6-dimethyl-4-[4-(benzoyloxy)phenyl]-1,4-dihydropyridine-3,5-dicarboxylate

Crystal data

C24H23NO6	F(000) = 888
Mr = 421.43	Dx = 1.299 Mg m^−3
Monoclinic, P21/n	Melting point = 438–440 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.8943 (6) Å	Cell parameters from 3795 reflections
b = 10.6426 (8) Å	θ = 5.0–42.7°
c = 25.7386 (18) Å	µ = 0.09 mm^−1
β = 94.642 (1)°	T = 273 K
V = 2155.4 (3) Å^3	Block, brown
Z = 4	0.09 × 0.08 × 0.04 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2786 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
Graphite monochromator	θmax = 25.0°, θmin = 1.6°
ω scans	h = −9→9
20310 measured reflections	k = −12→12
3799 independent reflections	l = −30→30

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0645P)^2 + 0.4502P] where P = (Fo^2 + 2Fc^2)/3
3799 reflections	(Δ/σ)max < 0.001
288 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.13 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
C2	0.5430 (3)	0.4695 (2)	0.28211 (8)	0.0558 (5)
C3	0.4850 (2)	0.41145 (19)	0.23784 (7)	0.0487 (5)
C4	0.4420 (2)	0.48486 (17)	0.18774 (7)	0.0437 (4)
H4	0.3329	0.4542	0.1718	0.052*
C5	0.4247 (2)	0.62447 (17)	0.19829 (7)	0.0443 (4)
C6	0.4851 (3)	0.67603 (19)	0.24388 (8)	0.0507 (5)
C7	0.5772 (2)	0.46038 (16)	0.14990 (7)	0.0426 (4)
C8	0.7397 (2)	0.50833 (17)	0.16007 (7)	0.0469 (5)
H8	0.7625	0.5615	0.1884	0.056*
C9	0.8687 (3)	0.47870 (18)	0.12892 (8)	0.0514 (5)
H9	0.9774	0.5114	0.1361	0.062*
C10	0.8336 (3)	0.4007 (2)	0.08746 (8)	0.0544 (5)
C11	0.6722 (3)	0.3561 (2)	0.07468 (8)	0.0648 (6)
H11	0.6492	0.3061	0.0453	0.078*
C12	0.5448 (3)	0.3869 (2)	0.10613 (8)	0.0577 (5)
H12	0.4351	0.3575	0.0976	0.069*
C13	0.6016 (4)	0.4091 (3)	0.33319 (9)	0.0832 (8)
H13A	0.5070	0.3688	0.3475	0.125*
H13B	0.6475	0.4722	0.3570	0.125*
H13C	0.6876	0.3479	0.3277	0.125*
C14	0.4709 (3)	0.2739 (2)	0.23510 (9)	0.0607 (6)
C15	0.3800 (4)	0.1030 (2)	0.18143 (12)	0.0936 (9)
H15A	0.4929	0.0689	0.1831	0.140*
H15B	0.3240	0.0872	0.1475	0.140*
H15C	0.3173	0.0639	0.2075	0.140*
C16	0.4879 (3)	0.8118 (2)	0.25817 (10)	0.0733 (7)
H16A	0.5900	0.8497	0.2476	0.110*
H16B	0.4847	0.8202	0.2952	0.110*
H16C	0.3909	0.8531	0.2409	0.110*
C17	0.3487 (2)	0.70276 (19)	0.15583 (7)	0.0493 (5)
C18	0.1903 (3)	0.6963 (2)	0.07367 (9)	0.0766 (7)
H18A	0.0957	0.7435	0.0845	0.115*
H18	0.1506	0.6364	0.0476	0.115*
H18C	0.2699	0.7524	0.0595	0.115*
C19	1.0314 (3)	0.2515 (2)	0.06369 (8)	0.0581 (5)
C20	1.1522 (3)	0.2190 (2)	0.02495 (8)	0.0548 (5)
C21	1.1932 (3)	0.0940 (2)	0.01905 (10)	0.0756 (7)
H21	1.1500	0.0336	0.0405	0.091*
C22	1.2980 (4)	0.0589 (3)	−0.01851 (12)	0.0905 (9)
H22	1.3224	−0.0256	−0.0232	0.109*
C23	1.3668 (3)	0.1483 (3)	−0.04913 (10)	0.0840 (8)
H23	1.4389	0.1242	−0.0742	0.101*
C24	1.3297 (3)	0.2718 (3)	−0.04292 (9)	0.0768 (7)
H24	1.3771	0.3320	−0.0635	0.092*
C25	1.2218 (3)	0.3080 (2)	−0.00617 (8)	0.0638 (6)
H25	1.1958	0.3925	−0.0023	0.077*
N1	0.5513 (2)	0.59885 (19)	0.28326 (7)	0.0618 (5)
H1	0.585 (3)	0.629 (2)	0.3113 (9)	0.068 (7)*
O1	0.5225 (3)	0.19990 (17)	0.26785 (8)	0.1091 (7)
O2	0.3886 (2)	0.23626 (13)	0.19058 (6)	0.0697 (4)
O3	0.3508 (2)	0.81515 (15)	0.15213 (6)	0.0833 (5)
O4	0.27200 (18)	0.63135 (13)	0.11766 (5)	0.0595 (4)
O5	0.96468 (19)	0.36720 (14)	0.05576 (5)	0.0643 (4)
O6	0.9916 (2)	0.18361 (17)	0.09791 (7)	0.0866 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.0543 (12)	0.0670 (15)	0.0466 (12)	0.0063 (10)	0.0065 (9)	0.0085 (10)
C3	0.0471 (11)	0.0513 (12)	0.0482 (11)	0.0053 (9)	0.0062 (9)	0.0083 (9)
C4	0.0443 (10)	0.0433 (11)	0.0427 (10)	−0.0014 (8)	−0.0008 (8)	0.0017 (8)
C5	0.0455 (10)	0.0434 (11)	0.0440 (10)	−0.0008 (8)	0.0047 (8)	−0.0007 (8)
C6	0.0524 (11)	0.0526 (12)	0.0471 (11)	−0.0029 (9)	0.0040 (9)	−0.0037 (9)
C7	0.0492 (11)	0.0394 (10)	0.0384 (10)	−0.0011 (8)	−0.0014 (8)	0.0026 (8)
C8	0.0537 (12)	0.0463 (11)	0.0403 (10)	−0.0022 (9)	0.0013 (9)	−0.0008 (8)
C9	0.0505 (11)	0.0530 (12)	0.0503 (11)	−0.0016 (9)	0.0012 (9)	0.0075 (10)
C10	0.0619 (13)	0.0567 (13)	0.0459 (11)	0.0070 (10)	0.0128 (10)	0.0080 (10)
C11	0.0731 (15)	0.0731 (15)	0.0487 (12)	−0.0038 (12)	0.0078 (11)	−0.0171 (11)
C12	0.0543 (12)	0.0683 (14)	0.0499 (12)	−0.0101 (10)	−0.0001 (10)	−0.0103 (10)
C13	0.0966 (19)	0.102 (2)	0.0493 (13)	0.0133 (16)	−0.0024 (13)	0.0179 (13)
C14	0.0582 (13)	0.0534 (13)	0.0709 (15)	0.0092 (10)	0.0067 (11)	0.0158 (12)
C15	0.115 (2)	0.0401 (13)	0.126 (2)	−0.0001 (14)	0.0164 (19)	−0.0040 (14)
C16	0.0916 (17)	0.0605 (14)	0.0674 (15)	−0.0090 (12)	0.0040 (13)	−0.0185 (12)
C17	0.0528 (12)	0.0459 (12)	0.0495 (11)	0.0029 (9)	0.0063 (9)	−0.0012 (9)
C18	0.0844 (17)	0.0895 (18)	0.0536 (13)	0.0085 (14)	−0.0092 (12)	0.0153 (12)
C19	0.0597 (13)	0.0654 (14)	0.0491 (12)	0.0036 (11)	0.0042 (10)	0.0073 (11)
C20	0.0506 (12)	0.0670 (14)	0.0459 (11)	0.0062 (10)	−0.0013 (9)	0.0010 (10)
C21	0.0701 (16)	0.0694 (16)	0.0889 (18)	0.0026 (12)	0.0151 (14)	−0.0052 (13)
C22	0.0818 (19)	0.0806 (19)	0.110 (2)	0.0096 (15)	0.0159 (17)	−0.0255 (18)
C23	0.0656 (16)	0.122 (2)	0.0653 (16)	0.0157 (16)	0.0094 (13)	−0.0167 (16)
C24	0.0647 (15)	0.109 (2)	0.0573 (14)	0.0155 (14)	0.0120 (12)	0.0160 (14)
C25	0.0618 (14)	0.0764 (15)	0.0533 (13)	0.0114 (11)	0.0059 (11)	0.0097 (11)
N1	0.0743 (13)	0.0672 (13)	0.0420 (10)	−0.0034 (10)	−0.0068 (9)	−0.0068 (9)
O1	0.1379 (18)	0.0668 (12)	0.1155 (16)	0.0121 (11)	−0.0335 (14)	0.0340 (11)
O2	0.0921 (11)	0.0415 (8)	0.0750 (11)	0.0006 (8)	0.0032 (9)	0.0019 (7)
O3	0.1258 (15)	0.0445 (10)	0.0765 (11)	0.0048 (9)	−0.0114 (10)	0.0065 (8)
O4	0.0683 (9)	0.0575 (9)	0.0500 (8)	0.0028 (7)	−0.0109 (7)	0.0060 (7)
O5	0.0750 (10)	0.0648 (10)	0.0561 (9)	0.0134 (8)	0.0248 (7)	0.0108 (7)
O6	0.1056 (14)	0.0809 (12)	0.0779 (11)	0.0211 (10)	0.0350 (10)	0.0289 (9)

Geometric parameters (Å, º)

C2—C3	1.344 (3)	C15—O2	1.439 (3)
C2—N1	1.378 (3)	C15—H15A	0.9600
C2—C13	1.502 (3)	C15—H15B	0.9600
C3—C14	1.470 (3)	C15—H15C	0.9600
C3—C4	1.522 (2)	C16—H16A	0.9600
C4—C5	1.519 (3)	C16—H16B	0.9600
C4—C7	1.524 (3)	C16—H16C	0.9600
C4—H4	0.9800	C17—O3	1.200 (2)
C5—C6	1.347 (3)	C17—O4	1.346 (2)
C5—C17	1.464 (3)	C18—O4	1.434 (2)
C6—N1	1.375 (3)	C18—H18A	0.9600
C6—C16	1.491 (3)	C18—H18	0.9600
C7—C12	1.379 (3)	C18—H18C	0.9600
C7—C8	1.386 (3)	C19—O6	1.201 (2)
C8—C9	1.383 (3)	C19—O5	1.348 (3)
C8—H8	0.9300	C19—C20	1.476 (3)
C9—C10	1.363 (3)	C20—C21	1.380 (3)
C9—H9	0.9300	C20—C25	1.383 (3)
C10—C11	1.374 (3)	C21—C22	1.374 (3)
C10—O5	1.415 (2)	C21—H21	0.9300
C11—C12	1.380 (3)	C22—C23	1.375 (4)
C11—H11	0.9300	C22—H22	0.9300
C12—H12	0.9300	C23—C24	1.358 (4)
C13—H13A	0.9600	C23—H23	0.9300
C13—H13B	0.9600	C24—C25	1.378 (3)
C13—H13C	0.9600	C24—H24	0.9300
C14—O1	1.201 (3)	C25—H25	0.9300
C14—O2	1.332 (3)	N1—H1	0.81 (2)
C3—C2—N1	119.33 (19)	H15A—C15—H15B	109.5
C3—C2—C13	127.2 (2)	O2—C15—H15C	109.5
N1—C2—C13	113.4 (2)	H15A—C15—H15C	109.5
C2—C3—C14	121.22 (19)	H15B—C15—H15C	109.5
C2—C3—C4	121.31 (18)	C6—C16—H16A	109.5
C14—C3—C4	117.37 (18)	C6—C16—H16B	109.5
C5—C4—C3	111.58 (15)	H16A—C16—H16B	109.5
C5—C4—C7	111.05 (15)	C6—C16—H16C	109.5
C3—C4—C7	109.50 (15)	H16A—C16—H16C	109.5
C5—C4—H4	108.2	H16B—C16—H16C	109.5
C3—C4—H4	108.2	O3—C17—O4	120.86 (18)
C7—C4—H4	108.2	O3—C17—C5	128.25 (19)
C6—C5—C17	120.88 (18)	O4—C17—C5	110.88 (17)
C6—C5—C4	121.59 (17)	O4—C18—H18A	109.5
C17—C5—C4	117.44 (16)	O4—C18—H18	109.5
C5—C6—N1	119.05 (19)	H18A—C18—H18	109.5
C5—C6—C16	127.36 (19)	O4—C18—H18C	109.5
N1—C6—C16	113.58 (18)	H18A—C18—H18C	109.5
C12—C7—C8	118.11 (18)	H18—C18—H18C	109.5
C12—C7—C4	121.73 (17)	O6—C19—O5	122.6 (2)
C8—C7—C4	120.11 (16)	O6—C19—C20	125.2 (2)
C9—C8—C7	121.37 (18)	O5—C19—C20	112.21 (18)
C9—C8—H8	119.3	C21—C20—C25	119.3 (2)
C7—C8—H8	119.3	C21—C20—C19	118.1 (2)
C10—C9—C8	118.69 (19)	C25—C20—C19	122.7 (2)
C10—C9—H9	120.7	C22—C21—C20	119.9 (3)
C8—C9—H9	120.7	C22—C21—H21	120.0
C9—C10—C11	121.59 (19)	C20—C21—H21	120.0
C9—C10—O5	119.54 (19)	C21—C22—C23	120.2 (3)
C11—C10—O5	118.85 (19)	C21—C22—H22	119.9
C10—C11—C12	118.90 (19)	C23—C22—H22	119.9
C10—C11—H11	120.5	C24—C23—C22	120.2 (3)
C12—C11—H11	120.5	C24—C23—H23	119.9
C7—C12—C11	121.18 (19)	C22—C23—H23	119.9
C7—C12—H12	119.4	C23—C24—C25	120.2 (3)
C11—C12—H12	119.4	C23—C24—H24	119.9
C2—C13—H13A	109.5	C25—C24—H24	119.9
C2—C13—H13B	109.5	C24—C25—C20	120.2 (2)
H13A—C13—H13B	109.5	C24—C25—H25	119.9
C2—C13—H13C	109.5	C20—C25—H25	119.9
H13A—C13—H13C	109.5	C6—N1—C2	124.50 (19)
H13B—C13—H13C	109.5	C6—N1—H1	119.8 (17)
O1—C14—O2	121.4 (2)	C2—N1—H1	114.9 (17)
O1—C14—C3	126.8 (2)	C14—O2—C15	116.79 (19)
O2—C14—C3	111.76 (18)	C17—O4—C18	116.80 (17)
O2—C15—H15A	109.5	C19—O5—C10	115.98 (15)
O2—C15—H15B	109.5
N1—C2—C3—C14	−178.80 (18)	C4—C3—C14—O1	168.1 (2)
C13—C2—C3—C14	0.6 (3)	C2—C3—C14—O2	171.00 (19)
N1—C2—C3—C4	5.1 (3)	C4—C3—C14—O2	−12.7 (3)
C13—C2—C3—C4	−175.5 (2)	C6—C5—C17—O3	11.3 (3)
C2—C3—C4—C5	−16.1 (3)	C4—C5—C17—O3	−165.2 (2)
C14—C3—C4—C5	167.64 (16)	C6—C5—C17—O4	−169.72 (18)
C2—C3—C4—C7	107.3 (2)	C4—C5—C17—O4	13.8 (2)
C14—C3—C4—C7	−69.0 (2)	O6—C19—C20—C21	16.1 (3)
C3—C4—C5—C6	16.3 (3)	O5—C19—C20—C21	−162.2 (2)
C7—C4—C5—C6	−106.2 (2)	O6—C19—C20—C25	−165.5 (2)
C3—C4—C5—C17	−167.23 (16)	O5—C19—C20—C25	16.2 (3)
C7—C4—C5—C17	70.3 (2)	C25—C20—C21—C22	−2.0 (3)
C17—C5—C6—N1	178.25 (18)	C19—C20—C21—C22	176.5 (2)
C4—C5—C6—N1	−5.4 (3)	C20—C21—C22—C23	2.2 (4)
C17—C5—C6—C16	−1.0 (3)	C21—C22—C23—C24	−0.9 (4)
C4—C5—C6—C16	175.4 (2)	C22—C23—C24—C25	−0.5 (4)
C5—C4—C7—C12	−128.96 (19)	C23—C24—C25—C20	0.7 (3)
C3—C4—C7—C12	107.4 (2)	C21—C20—C25—C24	0.6 (3)
C5—C4—C7—C8	53.6 (2)	C19—C20—C25—C24	−177.8 (2)
C3—C4—C7—C8	−70.1 (2)	C5—C6—N1—C2	−8.1 (3)
C12—C7—C8—C9	−3.2 (3)	C16—C6—N1—C2	171.2 (2)
C4—C7—C8—C9	174.32 (16)	C3—C2—N1—C6	8.2 (3)
C7—C8—C9—C10	0.1 (3)	C13—C2—N1—C6	−171.3 (2)
C8—C9—C10—C11	3.1 (3)	O1—C14—O2—C15	−6.2 (3)
C8—C9—C10—O5	−178.71 (16)	C3—C14—O2—C15	174.67 (19)
C9—C10—C11—C12	−3.0 (3)	O3—C17—O4—C18	−1.6 (3)
O5—C10—C11—C12	178.84 (19)	C5—C17—O4—C18	179.39 (17)
C8—C7—C12—C11	3.4 (3)	O6—C19—O5—C10	−5.1 (3)
C4—C7—C12—C11	−174.13 (19)	C20—C19—O5—C10	173.21 (17)
C10—C11—C12—C7	−0.4 (3)	C9—C10—O5—C19	102.5 (2)
C2—C3—C14—O1	−8.1 (4)	C11—C10—O5—C19	−79.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6^i	0.81 (2)	2.53 (2)	3.233 (3)	146 (2)
C8—H8···O1^i	0.93	2.45	3.249 (3)	144
C16—H16C···O3	0.96	2.32	2.854 (3)	115
C13—H13C···O1	0.96	2.50	2.830 (4)	100

Symmetry code: (i) −x+3/2, y+1/2, −z+1/2.