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The title compound, C17H18N2O6, is an important inter­mediate in the synthesis of nefidipine analogs. The crystal packing is stabilized by inter­molecular N—H...O hydrogen bonds and O—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806045570/om2065sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806045570/om2065Isup2.hkl
Contains datablock I

CCDC reference: 630209

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.051
  • wR factor = 0.149
  • Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.85 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.61 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8 PLAT301_ALERT_3_C Main Residue Disorder ......................... 4.00 Perc. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 29.90 Deg. C10 -C9 -C10' 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Ethyl 3-carboxy-2,6-dimethyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3-carboxylate top
Crystal data top
C17H18N2O6Dx = 1.343 Mg m3
Mr = 346.33Melting point = 446–447 K
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.323 (2) ÅCell parameters from 2043 reflections
b = 15.590 (3) Åθ = 2.3–23.4°
c = 11.202 (3) ŵ = 0.10 mm1
β = 108.201 (4)°T = 294 K
V = 1712.7 (7) Å3Block, yellow
Z = 40.40 × 0.28 × 0.10 mm
F(000) = 728
Data collection top
Bruker SMART CCD area-detector
diffractometer
3024 independent reflections
Radiation source: fine-focus sealed tube1890 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
φ and ω scansθmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1210
Tmin = 0.960, Tmax = 0.990k = 1518
8538 measured reflectionsl = 1313
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0635P)2 + 0.8733P]
where P = (Fo2 + 2Fc2)/3
3024 reflections(Δ/σ)max = 0.003
239 parametersΔρmax = 0.25 e Å3
20 restraintsΔρmin = 0.20 e Å3
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
O11.0062 (3)0.39646 (17)0.1318 (2)0.0863 (9)
O21.0692 (2)0.36792 (14)0.33350 (19)0.0691 (7)
O30.4342 (3)0.41885 (17)0.5179 (3)0.0891 (9)
O40.6007 (3)0.4136 (2)0.6913 (3)0.1034 (10)
O50.9897 (2)0.10382 (12)0.47880 (18)0.0554 (6)
O60.8608 (2)0.00384 (12)0.35777 (19)0.0644 (7)
H60.90940.02710.41300.097*
N10.7219 (2)0.19326 (14)0.08153 (19)0.0410 (6)
H10.64980.18920.01740.049*
N20.5510 (4)0.40028 (19)0.5787 (3)0.0725 (8)
C10.8078 (3)0.26264 (16)0.0895 (2)0.0376 (6)
C20.8931 (3)0.28520 (16)0.2031 (2)0.0369 (6)
C30.8847 (3)0.23861 (15)0.3189 (2)0.0361 (6)
H30.97740.23560.37810.043*
C40.8357 (3)0.14722 (16)0.2866 (2)0.0367 (6)
C50.7471 (3)0.13044 (16)0.1722 (2)0.0376 (6)
C60.6713 (3)0.04851 (19)0.1265 (3)0.0539 (8)
H6A0.72620.01170.09320.081*
H6B0.58740.06120.06190.081*
H6C0.65190.02030.19520.081*
C70.7948 (3)0.3025 (2)0.0357 (3)0.0545 (8)
H7A0.76620.36110.03580.082*
H7B0.72840.27150.10070.082*
H7C0.88130.30050.05070.082*
C80.9965 (3)0.35184 (18)0.2290 (3)0.0441 (7)
C91.1164 (4)0.4600 (3)0.1573 (4)0.0979 (15)
H9A1.08720.50920.10260.118*
H9B1.13980.47950.24370.118*
C101.2350 (11)0.4200 (11)0.135 (2)0.103 (5)0.54 (3)
H10A1.28460.38760.20810.155*0.54 (3)
H10B1.29300.46370.11930.155*0.54 (3)
H10C1.20520.38250.06400.155*0.54 (3)
C10'1.200 (2)0.4413 (9)0.072 (2)0.095 (5)0.46 (3)
H10D1.16070.47070.00660.142*0.46 (3)
H10E1.19960.38070.05690.142*0.46 (3)
H10F1.29140.46070.11030.142*0.46 (3)
C110.7962 (3)0.28407 (15)0.3858 (2)0.0383 (6)
C120.6724 (3)0.31877 (19)0.3207 (3)0.0534 (8)
H120.64280.31690.23330.064*
C130.5904 (3)0.3567 (2)0.3835 (3)0.0617 (9)
H130.50570.37940.33900.074*
C140.6362 (3)0.36014 (19)0.5115 (3)0.0535 (8)
C150.7605 (4)0.3280 (2)0.5786 (3)0.0674 (9)
H150.79110.33200.66580.081*
C160.8396 (3)0.2898 (2)0.5157 (3)0.0570 (8)
H160.92400.26720.56100.068*
C170.8992 (3)0.08299 (17)0.3805 (2)0.0425 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0946 (18)0.1036 (19)0.0502 (13)0.0592 (16)0.0071 (12)0.0166 (13)
O20.0752 (15)0.0648 (14)0.0461 (13)0.0270 (12)0.0114 (11)0.0100 (11)
O30.0821 (19)0.0799 (19)0.129 (2)0.0025 (15)0.0669 (19)0.0002 (16)
O40.124 (2)0.120 (2)0.088 (2)0.0030 (19)0.064 (2)0.0296 (18)
O50.0688 (13)0.0407 (11)0.0413 (11)0.0016 (10)0.0051 (10)0.0087 (9)
O60.0848 (16)0.0351 (12)0.0550 (13)0.0005 (11)0.0044 (11)0.0100 (9)
N10.0357 (12)0.0417 (13)0.0361 (12)0.0007 (10)0.0026 (10)0.0065 (10)
N20.083 (2)0.0625 (19)0.091 (2)0.0087 (17)0.055 (2)0.0065 (17)
C10.0378 (14)0.0371 (15)0.0349 (14)0.0044 (12)0.0071 (12)0.0065 (12)
C20.0370 (14)0.0373 (15)0.0334 (14)0.0019 (12)0.0065 (11)0.0062 (11)
C30.0359 (14)0.0351 (14)0.0318 (14)0.0021 (11)0.0024 (11)0.0048 (11)
C40.0402 (14)0.0337 (14)0.0341 (14)0.0018 (12)0.0086 (12)0.0039 (11)
C50.0387 (14)0.0331 (14)0.0398 (15)0.0030 (12)0.0106 (12)0.0021 (12)
C60.0552 (18)0.0452 (17)0.0519 (18)0.0075 (14)0.0034 (14)0.0003 (14)
C70.0597 (19)0.0614 (19)0.0361 (15)0.0060 (15)0.0059 (14)0.0108 (14)
C80.0449 (16)0.0414 (16)0.0404 (16)0.0014 (13)0.0050 (13)0.0094 (13)
C90.108 (3)0.111 (3)0.071 (3)0.059 (3)0.022 (2)0.013 (2)
C100.075 (6)0.115 (8)0.114 (8)0.023 (5)0.022 (5)0.007 (6)
C10'0.074 (7)0.078 (7)0.137 (9)0.000 (5)0.040 (7)0.017 (6)
C110.0456 (16)0.0282 (14)0.0378 (14)0.0012 (12)0.0085 (12)0.0033 (11)
C120.0554 (19)0.0581 (19)0.0428 (16)0.0115 (15)0.0094 (15)0.0002 (14)
C130.0501 (18)0.062 (2)0.072 (2)0.0096 (16)0.0171 (17)0.0017 (17)
C140.067 (2)0.0424 (17)0.062 (2)0.0069 (15)0.0359 (18)0.0064 (15)
C150.085 (3)0.076 (2)0.0440 (18)0.010 (2)0.0234 (18)0.0016 (17)
C160.0624 (19)0.070 (2)0.0360 (16)0.0106 (17)0.0116 (14)0.0004 (15)
C170.0504 (17)0.0356 (16)0.0386 (16)0.0013 (13)0.0096 (14)0.0022 (12)
Geometric parameters (Å, º) top
O1—C81.322 (3)C6—H6C0.9600
O1—C91.468 (4)C7—H7A0.9600
O2—C81.203 (3)C7—H7B0.9600
O3—N21.220 (4)C7—H7C0.9600
O4—N21.221 (4)C9—C101.462 (8)
O5—C171.244 (3)C9—C10'1.501 (9)
O6—C171.297 (3)C9—H9A0.9700
O6—H60.8200C9—H9B0.9700
N1—C51.376 (3)C10—H10A0.9600
N1—C11.384 (3)C10—H10B0.9600
N1—H10.8600C10—H10C0.9600
N2—C141.465 (4)C10'—H10D0.9600
C1—C21.349 (3)C10'—H10E0.9600
C1—C71.502 (4)C10'—H10F0.9600
C2—C81.452 (4)C11—C121.370 (4)
C2—C31.512 (3)C11—C161.385 (4)
C3—C41.517 (3)C12—C131.391 (4)
C3—C111.525 (4)C12—H120.9300
C3—H30.9800C13—C141.363 (4)
C4—C51.347 (3)C13—H130.9300
C4—C171.452 (4)C14—C151.364 (4)
C5—C61.502 (4)C15—C161.371 (4)
C6—H6A0.9600C15—H150.9300
C6—H6B0.9600C16—H160.9300
C8—O1—C9116.7 (2)C10—C9—C10'29.9 (5)
C17—O6—H6109.5O1—C9—C10'107.9 (6)
C5—N1—C1122.6 (2)C10—C9—H9A110.0
C5—N1—H1118.7O1—C9—H9A110.0
C1—N1—H1118.7C10'—C9—H9A82.9
O3—N2—O4124.0 (3)C10—C9—H9B110.0
O3—N2—C14117.5 (3)O1—C9—H9B110.0
O4—N2—C14118.5 (4)C10'—C9—H9B133.2
C2—C1—N1118.7 (2)H9A—C9—H9B108.4
C2—C1—C7128.0 (2)C9—C10—H10A109.5
N1—C1—C7113.3 (2)C9—C10—H10B109.5
C1—C2—C8126.7 (2)H10A—C10—H10B109.5
C1—C2—C3119.3 (2)C9—C10—H10C109.5
C8—C2—C3114.1 (2)H10A—C10—H10C109.5
C2—C3—C4110.5 (2)H10B—C10—H10C109.5
C2—C3—C11113.7 (2)C9—C10'—H10D109.5
C4—C3—C11110.3 (2)C9—C10'—H10E109.5
C2—C3—H3107.3H10D—C10'—H10E109.5
C4—C3—H3107.3C9—C10'—H10F109.5
C11—C3—H3107.3H10D—C10'—H10F109.5
C5—C4—C17125.0 (2)H10E—C10'—H10F109.5
C5—C4—C3119.1 (2)C12—C11—C16118.4 (3)
C17—C4—C3115.7 (2)C12—C11—C3121.6 (2)
C4—C5—N1118.7 (2)C16—C11—C3120.0 (2)
C4—C5—C6128.0 (2)C11—C12—C13120.9 (3)
N1—C5—C6113.3 (2)C11—C12—H12119.6
C5—C6—H6A109.5C13—C12—H12119.6
C5—C6—H6B109.5C14—C13—C12118.8 (3)
H6A—C6—H6B109.5C14—C13—H13120.6
C5—C6—H6C109.5C12—C13—H13120.6
H6A—C6—H6C109.5C13—C14—C15121.6 (3)
H6B—C6—H6C109.5C13—C14—N2119.3 (3)
C1—C7—H7A109.5C15—C14—N2119.1 (3)
C1—C7—H7B109.5C14—C15—C16119.0 (3)
H7A—C7—H7B109.5C14—C15—H15120.5
C1—C7—H7C109.5C16—C15—H15120.5
H7A—C7—H7C109.5C15—C16—C11121.3 (3)
H7B—C7—H7C109.5C15—C16—H16119.3
O2—C8—O1120.4 (3)C11—C16—H16119.3
O2—C8—C2122.6 (2)O5—C17—O6121.4 (2)
O1—C8—C2116.9 (2)O5—C17—C4120.4 (2)
C10—C9—O1108.5 (6)O6—C17—C4118.2 (2)
C5—N1—C1—C221.4 (4)C3—C2—C8—O1178.2 (3)
C5—N1—C1—C7157.0 (2)C8—O1—C9—C1093.8 (11)
N1—C1—C2—C8175.4 (2)C8—O1—C9—C10'125.3 (11)
C7—C1—C2—C82.7 (5)C2—C3—C11—C1243.8 (3)
N1—C1—C2—C34.6 (4)C4—C3—C11—C1281.0 (3)
C7—C1—C2—C3177.2 (3)C2—C3—C11—C16137.3 (3)
C1—C2—C3—C429.4 (3)C4—C3—C11—C1697.9 (3)
C8—C2—C3—C4150.7 (2)C16—C11—C12—C131.8 (4)
C1—C2—C3—C1195.3 (3)C3—C11—C12—C13177.2 (3)
C8—C2—C3—C1184.6 (3)C11—C12—C13—C141.1 (5)
C2—C3—C4—C532.7 (3)C12—C13—C14—C150.6 (5)
C11—C3—C4—C593.9 (3)C12—C13—C14—N2179.7 (3)
C2—C3—C4—C17142.2 (2)O3—N2—C14—C139.6 (4)
C11—C3—C4—C1791.2 (3)O4—N2—C14—C13170.0 (3)
C17—C4—C5—N1163.5 (2)O3—N2—C14—C15171.2 (3)
C3—C4—C5—N110.9 (4)O4—N2—C14—C159.2 (5)
C17—C4—C5—C614.7 (5)C13—C14—C15—C161.4 (5)
C3—C4—C5—C6170.9 (3)N2—C14—C15—C16179.4 (3)
C1—N1—C5—C418.1 (4)C14—C15—C16—C110.7 (5)
C1—N1—C5—C6160.4 (2)C12—C11—C16—C150.9 (5)
C9—O1—C8—O25.1 (5)C3—C11—C16—C15178.0 (3)
C9—O1—C8—C2176.3 (3)C5—C4—C17—O5173.1 (3)
C1—C2—C8—O2179.7 (3)C3—C4—C17—O51.5 (4)
C3—C2—C8—O20.4 (4)C5—C4—C17—O65.6 (4)
C1—C2—C8—O11.7 (4)C3—C4—C17—O6179.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.862.162.894 (3)143
O6—H6···O5ii0.821.792.605 (3)174
Symmetry codes: (i) x1/2, y+1/2, z1/2; (ii) x+2, y, z+1.
 

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