Diethyl 4-(1H-imidazol-2-yl)-2,6-dimethyl-1,4-di­hydro­pyridine-3,5-di­carboxyl­ate

In the title compound, C₁₆H₂₁N₃O₄, the 1,4-di­hydro­pyridine ring adopts a flattened boat conformation, with the imidazole substituent in an axial orientation [dihedral angle between ring planes = 82.9 (6)°]. In the crystal structure, pairs of N—H...O and N—H...N hydrogen bonds with graph-set notation R₂²(14) connect the mol­ecules into chains running along the c-axis direction.

Key indicators

• Single-crystal X-ray study
• T = 223 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.049
• wR factor = 0.142
• Data-to-parameter ratio = 18.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT148_ALERT_3_C s.u. on the      b    - Axis is (Too) Large ....      0.009 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600        108 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT019_ALERT_1_G _diffrn_measured_fraction_theta_full/*_max < 1.0      0.993 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         13 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         12 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 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

   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
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Diethyl 4-(1H-imidazol-2-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Crystal data

C16H21N3O4	Z = 2
Mr = 319.36	F(000) = 340
Triclinic, P1	Dx = 1.301 Mg m^−3
a = 8.127 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.411 (9) Å	Cell parameters from 9982 reflections
c = 12.536 (10) Å	θ = 2.5–28.3°
α = 105.36 (4)°	µ = 0.10 mm^−1
β = 96.52 (2)°	T = 223 K
γ = 94.77 (3)°	Block, colourless
V = 815.1 (13) Å^3	0.28 × 0.21 × 0.14 mm

Data collection

PHOTON 100 CMOS diffractometer	3144 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.041
Absorption correction: multi-scan (SADABS; Bruker, 2012)	θmax = 28.3°, θmin = 2.5°
Tmin = 0.974, Tmax = 0.987	h = −10→10
33431 measured reflections	k = −11→11
3920 independent reflections	l = −16→16

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.049	H-atom parameters constrained
wR(F^2) = 0.142	w = 1/[σ^2(Fo^2) + (0.0734P)^2 + 0.2436P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
3920 reflections	Δρmax = 0.32 e Å^−3
212 parameters	Δρmin = −0.23 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.18302 (15)	0.47356 (14)	0.46454 (9)	0.0280 (3)
H1	0.1979	0.5159	0.5367	0.034*
C1	0.21728 (16)	0.57673 (16)	0.39890 (11)	0.0251 (3)
C2	0.16729 (15)	0.52079 (16)	0.28644 (10)	0.0232 (3)
C3	0.04796 (16)	0.36033 (15)	0.23758 (10)	0.0229 (3)
H3	0.0781	0.3040	0.1637	0.028*
C4	0.06773 (16)	0.24414 (16)	0.31144 (11)	0.0253 (3)
C5	0.12622 (16)	0.30616 (17)	0.42189 (11)	0.0261 (3)
C6	0.3103 (2)	0.74263 (19)	0.46493 (12)	0.0374 (4)
H6A	0.4280	0.7424	0.4580	0.056*
H6B	0.2959	0.7626	0.5430	0.056*
H6C	0.2669	0.8296	0.4363	0.056*
C7	0.21403 (16)	0.60658 (17)	0.20487 (11)	0.0258 (3)
O1	0.15784 (14)	0.55990 (13)	0.10544 (8)	0.0368 (3)
O2	0.32952 (13)	0.73897 (13)	0.24786 (8)	0.0333 (3)
C8	0.3728 (2)	0.83898 (19)	0.17506 (13)	0.0387 (4)
H8A	0.2719	0.8672	0.1369	0.046*
H8B	0.4361	0.7785	0.1186	0.046*
C9	0.4771 (3)	0.9939 (2)	0.24842 (16)	0.0521 (5)
H9A	0.4123	1.0534	0.3030	0.078*
H9B	0.5110	1.0643	0.2028	0.078*
H9C	0.5754	0.9640	0.2867	0.078*
C10	−0.13059 (16)	0.39732 (15)	0.21997 (10)	0.0231 (3)
N2	−0.20049 (15)	0.42932 (16)	0.12553 (10)	0.0315 (3)
H2	−0.1525	0.4293	0.0669	0.038*
C11	−0.36104 (19)	0.4617 (2)	0.13918 (13)	0.0384 (4)
H11	−0.4397	0.4889	0.0878	0.046*
C12	−0.38247 (19)	0.4467 (2)	0.24119 (13)	0.0373 (3)
H12	−0.4814	0.4613	0.2730	0.045*
N3	−0.23804 (14)	0.40668 (16)	0.29244 (9)	0.0302 (3)
C13	0.00797 (18)	0.06611 (17)	0.26232 (12)	0.0308 (3)
O3	0.02408 (19)	−0.04606 (14)	0.30548 (11)	0.0556 (4)
O4	−0.07121 (14)	0.03801 (12)	0.15720 (9)	0.0360 (3)
C14	−0.1454 (2)	−0.13100 (19)	0.10123 (14)	0.0406 (4)
H14A	−0.2060	−0.1768	0.1517	0.049*
H14B	−0.0586	−0.2015	0.0776	0.049*
C15	−0.2623 (2)	−0.1240 (2)	0.00188 (14)	0.0441 (4)
H15A	−0.3471	−0.0535	0.0264	0.066*
H15B	−0.3149	−0.2350	−0.0377	0.066*
H15C	−0.2006	−0.0790	−0.0475	0.066*
C16	0.1393 (2)	0.2112 (2)	0.50829 (13)	0.0372 (4)
H16A	0.0529	0.1174	0.4870	0.056*
H16B	0.1256	0.2835	0.5803	0.056*
H16C	0.2479	0.1716	0.5132	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0361 (6)	0.0299 (6)	0.0185 (5)	0.0004 (5)	0.0041 (4)	0.0086 (4)
C1	0.0256 (6)	0.0272 (6)	0.0237 (6)	0.0016 (5)	0.0050 (5)	0.0090 (5)
C2	0.0240 (6)	0.0247 (6)	0.0222 (6)	0.0008 (5)	0.0045 (5)	0.0088 (5)
C3	0.0280 (6)	0.0228 (6)	0.0186 (6)	0.0010 (5)	0.0044 (5)	0.0068 (4)
C4	0.0273 (6)	0.0246 (6)	0.0269 (6)	0.0043 (5)	0.0060 (5)	0.0111 (5)
C5	0.0268 (6)	0.0288 (7)	0.0265 (6)	0.0045 (5)	0.0061 (5)	0.0130 (5)
C6	0.0467 (9)	0.0365 (8)	0.0239 (7)	−0.0088 (7)	0.0006 (6)	0.0055 (6)
C7	0.0272 (6)	0.0277 (6)	0.0236 (6)	0.0010 (5)	0.0049 (5)	0.0092 (5)
O1	0.0488 (6)	0.0388 (6)	0.0221 (5)	−0.0082 (5)	0.0029 (4)	0.0124 (4)
O2	0.0368 (6)	0.0343 (5)	0.0292 (5)	−0.0092 (4)	0.0029 (4)	0.0144 (4)
C8	0.0481 (9)	0.0347 (8)	0.0352 (8)	−0.0084 (7)	0.0090 (7)	0.0158 (6)
C9	0.0616 (12)	0.0394 (9)	0.0509 (10)	−0.0158 (8)	0.0143 (9)	0.0092 (8)
C10	0.0296 (6)	0.0211 (6)	0.0170 (6)	−0.0020 (5)	0.0001 (5)	0.0055 (4)
N2	0.0356 (6)	0.0397 (7)	0.0216 (6)	0.0011 (5)	0.0005 (4)	0.0147 (5)
C11	0.0332 (8)	0.0492 (9)	0.0336 (8)	0.0043 (7)	−0.0072 (6)	0.0180 (7)
C12	0.0272 (7)	0.0506 (9)	0.0353 (8)	0.0071 (6)	0.0013 (6)	0.0144 (7)
N3	0.0274 (6)	0.0424 (7)	0.0228 (6)	0.0058 (5)	0.0034 (4)	0.0119 (5)
C13	0.0350 (7)	0.0270 (7)	0.0325 (7)	0.0034 (5)	0.0064 (6)	0.0113 (5)
O3	0.0870 (10)	0.0298 (6)	0.0494 (7)	−0.0010 (6)	−0.0086 (7)	0.0200 (5)
O4	0.0481 (6)	0.0242 (5)	0.0332 (6)	−0.0033 (4)	0.0001 (5)	0.0083 (4)
C14	0.0466 (9)	0.0245 (7)	0.0461 (9)	−0.0043 (6)	0.0013 (7)	0.0065 (6)
C15	0.0401 (9)	0.0456 (9)	0.0402 (9)	−0.0039 (7)	0.0046 (7)	0.0040 (7)
C16	0.0491 (9)	0.0376 (8)	0.0299 (7)	0.0046 (7)	0.0038 (6)	0.0187 (6)

Geometric parameters (Å, º)

N1—C1	1.3777 (19)	C9—H9B	0.9700
N1—C5	1.385 (2)	C9—H9C	0.9700
N1—H1	0.8700	C10—N3	1.3221 (19)
C1—C2	1.364 (2)	C10—N2	1.3558 (19)
C1—C6	1.508 (2)	N2—C11	1.375 (2)
C2—C7	1.464 (2)	N2—H2	0.8700
C2—C3	1.532 (2)	C11—C12	1.347 (2)
C3—C10	1.513 (2)	C11—H11	0.9400
C3—C4	1.520 (2)	C12—N3	1.383 (2)
C3—H3	0.9900	C12—H12	0.9400
C4—C5	1.357 (2)	C13—O3	1.214 (2)
C4—C13	1.476 (2)	C13—O4	1.350 (2)
C5—C16	1.506 (2)	O4—C14	1.452 (2)
C6—H6A	0.9700	C14—C15	1.496 (3)
C6—H6B	0.9700	C14—H14A	0.9800
C6—H6C	0.9700	C14—H14B	0.9800
C7—O1	1.2239 (19)	C15—H15A	0.9700
C7—O2	1.3434 (19)	C15—H15B	0.9700
O2—C8	1.4473 (19)	C15—H15C	0.9700
C8—C9	1.506 (2)	C16—H16A	0.9700
C8—H8A	0.9800	C16—H16B	0.9700
C8—H8B	0.9800	C16—H16C	0.9700
C9—H9A	0.9700
C1—N1—C5	123.55 (12)	H9A—C9—H9B	109.5
C1—N1—H1	118.2	C8—C9—H9C	109.5
C5—N1—H1	118.2	H9A—C9—H9C	109.5
C2—C1—N1	118.86 (13)	H9B—C9—H9C	109.5
C2—C1—C6	128.14 (12)	N3—C10—N2	110.72 (13)
N1—C1—C6	113.00 (13)	N3—C10—C3	126.17 (12)
C1—C2—C7	124.90 (13)	N2—C10—C3	123.10 (12)
C1—C2—C3	120.01 (11)	C10—N2—C11	107.57 (12)
C7—C2—C3	115.05 (12)	C10—N2—H2	126.2
C10—C3—C4	111.44 (10)	C11—N2—H2	126.2
C10—C3—C2	111.01 (12)	C12—C11—N2	105.92 (13)
C4—C3—C2	110.65 (12)	C12—C11—H11	127.0
C10—C3—H3	107.9	N2—C11—H11	127.0
C4—C3—H3	107.9	C11—C12—N3	110.26 (14)
C2—C3—H3	107.9	C11—C12—H12	124.9
C5—C4—C13	121.28 (13)	N3—C12—H12	124.9
C5—C4—C3	120.13 (13)	C10—N3—C12	105.53 (13)
C13—C4—C3	118.36 (13)	O3—C13—O4	121.56 (14)
C4—C5—N1	119.54 (12)	O3—C13—C4	127.60 (15)
C4—C5—C16	126.95 (14)	O4—C13—C4	110.84 (12)
N1—C5—C16	113.51 (13)	C13—O4—C14	116.62 (12)
C1—C6—H6A	109.5	O4—C14—C15	106.98 (14)
C1—C6—H6B	109.5	O4—C14—H14A	110.3
H6A—C6—H6B	109.5	C15—C14—H14A	110.3
C1—C6—H6C	109.5	O4—C14—H14B	110.3
H6A—C6—H6C	109.5	C15—C14—H14B	110.3
H6B—C6—H6C	109.5	H14A—C14—H14B	108.6
O1—C7—O2	122.36 (12)	C14—C15—H15A	109.5
O1—C7—C2	123.54 (13)	C14—C15—H15B	109.5
O2—C7—C2	114.06 (12)	H15A—C15—H15B	109.5
C7—O2—C8	117.63 (12)	C14—C15—H15C	109.5
O2—C8—C9	106.51 (14)	H15A—C15—H15C	109.5
O2—C8—H8A	110.4	H15B—C15—H15C	109.5
C9—C8—H8A	110.4	C5—C16—H16A	109.5
O2—C8—H8B	110.4	C5—C16—H16B	109.5
C9—C8—H8B	110.4	H16A—C16—H16B	109.5
H8A—C8—H8B	108.6	C5—C16—H16C	109.5
C8—C9—H9A	109.5	H16A—C16—H16C	109.5
C8—C9—H9B	109.5	H16B—C16—H16C	109.5
C5—N1—C1—C2	11.5 (2)	C3—C2—C7—O2	−174.61 (11)
C5—N1—C1—C6	−168.01 (13)	O1—C7—O2—C8	7.2 (2)
N1—C1—C2—C7	−171.32 (12)	C2—C7—O2—C8	−175.03 (12)
C6—C1—C2—C7	8.1 (2)	C7—O2—C8—C9	169.35 (14)
N1—C1—C2—C3	11.18 (19)	C4—C3—C10—N3	32.28 (17)
C6—C1—C2—C3	−169.38 (13)	C2—C3—C10—N3	−91.54 (16)
C1—C2—C3—C10	96.34 (14)	C4—C3—C10—N2	−149.20 (12)
C7—C2—C3—C10	−81.40 (14)	C2—C3—C10—N2	86.98 (15)
C1—C2—C3—C4	−27.93 (17)	N3—C10—N2—C11	0.37 (16)
C7—C2—C3—C4	154.33 (11)	C3—C10—N2—C11	−178.36 (12)
C10—C3—C4—C5	−98.67 (15)	C10—N2—C11—C12	−0.51 (17)
C2—C3—C4—C5	25.35 (17)	N2—C11—C12—N3	0.48 (19)
C10—C3—C4—C13	75.95 (15)	N2—C10—N3—C12	−0.07 (16)
C2—C3—C4—C13	−160.02 (12)	C3—C10—N3—C12	178.60 (12)
C13—C4—C5—N1	179.24 (12)	C11—C12—N3—C10	−0.26 (18)
C3—C4—C5—N1	−6.29 (19)	C5—C4—C13—O3	−11.3 (2)
C13—C4—C5—C16	−0.2 (2)	C3—C4—C13—O3	174.13 (16)
C3—C4—C5—C16	174.29 (13)	C5—C4—C13—O4	169.00 (12)
C1—N1—C5—C4	−14.2 (2)	C3—C4—C13—O4	−5.56 (17)
C1—N1—C5—C16	165.30 (13)	O3—C13—O4—C14	3.9 (2)
C1—C2—C7—O1	−174.51 (14)	C4—C13—O4—C14	−176.41 (12)
C3—C2—C7—O1	3.1 (2)	C13—O4—C14—C15	165.03 (13)
C1—C2—C7—O2	7.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3^i	0.87	2.05	2.913 (3)	175
N2—H2···O1^ii	0.87	2.18	2.979 (3)	152

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