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The title compound, C27H28N2O7, has been synthesized by the reaction of 2-methoxy­ethyl 2-(3-nitro­benzyl­idene)aceto­acetate with cinnamyl 3-amino­crotonate and crystallized from methanol. The substituted 1,4-dihydro­pyridine ring adopts a flattened boat conformation. The 3-nitro­phenyl ring is approximately perpendicular to the mean plane of the 1,4-dihydro­pyridine ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806024883/xu2068sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806024883/xu2068Isup2.hkl
Contains datablock I

CCDC reference: 618346

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.051
  • wR factor = 0.152
  • Data-to-parameter ratio = 8.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.10 From the CIF: _reflns_number_total 2851 Count of symmetry unique reflns 2869 Completeness (_total/calc) 99.37% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).

3-Cinnamyl 5-(2-methoxyethyl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4- dihydropyridine-3,5-dicarboxylate top
Crystal data top
C27H28N2O7F(000) = 4160
Mr = 492.51Dx = 1.318 Mg m3
Orthorhombic, Fdd2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2dCell parameters from 5225 reflections
a = 15.1280 (8) Åθ = 2.3–23.7°
b = 59.932 (3) ŵ = 0.10 mm1
c = 10.9468 (5) ÅT = 173 K
V = 9924.9 (9) Å3Block, yellow
Z = 160.42 × 0.34 × 0.28 mm
Data collection top
Bruker AXS SMART 1000 CCD
diffractometer
2094 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.049
Graphite monochromatorθmax = 27.1°, θmin = 1.4°
ω scansh = 1919
20624 measured reflectionsk = 7676
2851 independent reflectionsl = 1314
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) = 0.152H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.099P)2]
where P = (Fo2 + 2Fc2)/3
2851 reflections(Δ/σ)max < 0.001
328 parametersΔρmax = 0.37 e Å3
1 restraintΔρmin = 0.26 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*/Ueq
C10.3543 (2)0.01137 (7)0.7285 (3)0.0369 (8)
C20.3371 (2)0.03293 (6)0.7004 (3)0.0344 (8)
C30.3102 (2)0.03957 (6)0.5718 (3)0.0310 (7)
H30.34180.05370.55100.037*
C40.3378 (2)0.02204 (6)0.4794 (3)0.0332 (8)
C50.3568 (2)0.00093 (6)0.5140 (4)0.0359 (8)
C60.3781 (3)0.01860 (7)0.4332 (5)0.0492 (10)
H6A0.33610.01910.36510.074*
H6B0.37380.03240.48060.074*
H6C0.43830.01700.40120.074*
C70.3721 (3)0.00209 (8)0.8531 (4)0.0478 (10)
H7A0.42690.00850.88530.072*
H7B0.37800.01420.84800.072*
H7C0.32290.00580.90770.072*
C80.2106 (2)0.04446 (6)0.5696 (3)0.0321 (7)
C90.1792 (2)0.06524 (6)0.5416 (3)0.0351 (8)
H90.21900.07680.51880.042*
C100.0893 (3)0.06936 (7)0.5465 (4)0.0421 (9)
C110.0287 (2)0.05288 (7)0.5762 (3)0.0433 (9)
H110.03300.05590.57680.052*
C120.0604 (2)0.03199 (7)0.6048 (4)0.0429 (9)
H120.02040.02040.62590.052*
C130.1512 (2)0.02779 (6)0.6030 (3)0.0357 (8)
H130.17270.01340.62470.043*
C140.3402 (2)0.02818 (6)0.3492 (3)0.0351 (8)
C150.2923 (2)0.05601 (8)0.2070 (4)0.0455 (9)
H15A0.29570.04340.14900.055*
H15B0.34070.06660.18810.055*
C160.2050 (2)0.06741 (6)0.1962 (4)0.0411 (9)
H16A0.19840.07850.26250.049*
H16B0.20150.07540.11710.049*
C170.0512 (3)0.06165 (8)0.2019 (5)0.0548 (11)
H17A0.04530.07180.27160.082*
H17B0.00590.05000.20730.082*
H17C0.04350.07000.12580.082*
C180.3381 (2)0.05035 (7)0.7946 (4)0.0400 (9)
C190.3386 (3)0.08990 (7)0.8248 (4)0.0493 (10)
H19A0.36670.10230.77950.059*
H19B0.37800.08590.89370.059*
C200.2527 (3)0.09757 (7)0.8741 (4)0.0501 (11)
H200.25400.11050.92450.060*
C210.1741 (3)0.08834 (7)0.8554 (4)0.0461 (10)
H210.17220.07540.80500.055*
C220.0900 (3)0.09623 (7)0.9053 (4)0.0464 (10)
C230.0113 (3)0.08458 (7)0.8765 (4)0.0517 (11)
H230.01330.07210.82290.062*
C240.0680 (3)0.09127 (7)0.9262 (4)0.0530 (11)
H240.12060.08340.90570.064*
C250.0722 (3)0.10910 (8)1.0050 (4)0.0548 (11)
H250.12730.11361.03880.066*
C260.0037 (3)0.12040 (7)1.0344 (5)0.0595 (12)
H260.00090.13261.08930.071*
C270.0840 (3)0.11425 (7)0.9854 (5)0.0551 (12)
H270.13580.12241.00640.066*
N10.3568 (2)0.00441 (5)0.6366 (3)0.0400 (8)
H1A0.35850.01860.65730.048*
N20.0566 (3)0.09177 (7)0.5230 (4)0.0547 (9)
O10.34709 (19)0.04759 (5)0.9044 (3)0.0512 (8)
O20.33051 (18)0.07082 (4)0.7441 (3)0.0449 (7)
O30.3722 (2)0.01767 (5)0.2669 (3)0.0593 (9)
O40.30053 (17)0.04799 (4)0.3317 (2)0.0414 (6)
O50.13673 (16)0.05162 (4)0.2036 (3)0.0447 (7)
O60.1071 (3)0.10508 (6)0.4729 (4)0.0831 (12)
O70.0191 (2)0.09652 (6)0.5532 (4)0.0730 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0299 (18)0.050 (2)0.0312 (19)0.0041 (15)0.0003 (15)0.0016 (16)
C20.0292 (17)0.041 (2)0.0332 (19)0.0026 (14)0.0008 (15)0.0009 (16)
C30.0282 (16)0.0376 (18)0.0271 (16)0.0021 (14)0.0021 (14)0.0018 (14)
C40.0272 (17)0.0388 (19)0.0338 (19)0.0034 (14)0.0000 (14)0.0019 (15)
C50.0289 (17)0.044 (2)0.0347 (19)0.0019 (15)0.0028 (15)0.0004 (17)
C60.055 (2)0.043 (2)0.051 (3)0.0039 (18)0.005 (2)0.0063 (19)
C70.043 (2)0.060 (3)0.040 (2)0.0002 (18)0.0056 (18)0.008 (2)
C80.0314 (16)0.0421 (19)0.0229 (16)0.0022 (14)0.0006 (13)0.0036 (15)
C90.0369 (18)0.0414 (19)0.0271 (18)0.0006 (15)0.0029 (15)0.0006 (15)
C100.043 (2)0.053 (2)0.0304 (19)0.0096 (17)0.0072 (16)0.0062 (17)
C110.0322 (18)0.063 (2)0.035 (2)0.0046 (18)0.0015 (16)0.0111 (19)
C120.0325 (18)0.057 (2)0.039 (2)0.0109 (17)0.0045 (16)0.0117 (18)
C130.0343 (18)0.0403 (19)0.0326 (19)0.0016 (15)0.0005 (16)0.0036 (15)
C140.0344 (18)0.0377 (19)0.0331 (19)0.0037 (15)0.0063 (16)0.0040 (16)
C150.038 (2)0.069 (3)0.0296 (19)0.0014 (19)0.0012 (16)0.0086 (19)
C160.045 (2)0.043 (2)0.036 (2)0.0048 (17)0.0044 (18)0.0079 (18)
C170.035 (2)0.073 (3)0.057 (3)0.0108 (19)0.001 (2)0.002 (2)
C180.0318 (18)0.052 (2)0.036 (2)0.0041 (16)0.0045 (16)0.0028 (18)
C190.058 (3)0.047 (2)0.043 (2)0.0055 (19)0.001 (2)0.0109 (19)
C200.060 (3)0.042 (2)0.049 (3)0.0006 (19)0.000 (2)0.0060 (19)
C210.061 (3)0.0397 (19)0.037 (2)0.0002 (19)0.001 (2)0.0045 (17)
C220.052 (2)0.046 (2)0.041 (2)0.0045 (19)0.0056 (18)0.0002 (18)
C230.069 (3)0.049 (2)0.037 (2)0.001 (2)0.006 (2)0.0025 (19)
C240.051 (2)0.056 (3)0.052 (3)0.006 (2)0.000 (2)0.004 (2)
C250.055 (3)0.061 (3)0.049 (3)0.011 (2)0.001 (2)0.001 (2)
C260.066 (3)0.048 (2)0.065 (3)0.012 (2)0.001 (3)0.011 (2)
C270.055 (3)0.043 (2)0.067 (3)0.0010 (18)0.005 (2)0.013 (2)
N10.0445 (18)0.0358 (16)0.0397 (19)0.0005 (14)0.0006 (14)0.0008 (14)
N20.057 (2)0.058 (2)0.049 (2)0.0154 (19)0.0100 (18)0.0038 (19)
O10.0591 (18)0.0631 (19)0.0313 (15)0.0031 (14)0.0100 (13)0.0043 (13)
O20.0492 (16)0.0453 (15)0.0401 (16)0.0011 (12)0.0064 (12)0.0083 (12)
O30.086 (2)0.0500 (17)0.0415 (16)0.0065 (15)0.0236 (17)0.0015 (14)
O40.0424 (14)0.0538 (16)0.0279 (13)0.0081 (12)0.0036 (11)0.0034 (12)
O50.0341 (13)0.0412 (14)0.0589 (18)0.0002 (11)0.0006 (13)0.0031 (14)
O60.091 (3)0.060 (2)0.098 (3)0.0250 (19)0.022 (2)0.026 (2)
O70.0553 (19)0.079 (2)0.084 (3)0.0296 (16)0.0127 (18)0.021 (2)
Geometric parameters (Å, º) top
C1—C21.353 (5)C15—H15A0.9900
C1—N11.381 (5)C15—H15B0.9900
C1—C71.498 (6)C16—O51.403 (4)
C2—C181.468 (5)C16—H16A0.9900
C2—C31.519 (5)C16—H16B0.9900
C3—C41.517 (5)C17—O51.427 (5)
C3—C81.535 (5)C17—H17A0.9800
C3—H31.0000C17—H17B0.9800
C4—C51.352 (5)C17—H17C0.9800
C4—C141.472 (5)C18—O11.221 (5)
C5—N11.380 (5)C18—O21.350 (5)
C5—C61.502 (5)C19—O21.450 (4)
C6—H6A0.9800C19—C201.481 (6)
C6—H6B0.9800C19—H19A0.9900
C6—H6C0.9800C19—H19B0.9900
C7—H7A0.9800C20—C211.328 (6)
C7—H7B0.9800C20—H200.9500
C7—H7C0.9800C21—C221.463 (6)
C8—C91.367 (5)C21—H210.9500
C8—C131.392 (5)C22—C271.394 (6)
C9—C101.384 (5)C22—C231.415 (6)
C9—H90.9500C23—C241.377 (6)
C10—C111.386 (6)C23—H230.9500
C10—N21.454 (5)C24—C251.375 (6)
C11—C121.377 (6)C24—H240.9500
C11—H110.9500C25—C261.371 (7)
C12—C131.398 (5)C25—H250.9500
C12—H120.9500C26—C271.378 (6)
C13—H130.9500C26—H260.9500
C14—O31.201 (5)C27—H270.9500
C14—O41.343 (4)N1—H1A0.8800
C15—O41.452 (5)N2—O71.226 (5)
C15—C161.492 (5)N2—O61.233 (5)
C2—C1—N1119.6 (3)H15A—C15—H15B108.5
C2—C1—C7126.6 (4)O5—C16—C15109.7 (3)
N1—C1—C7113.8 (3)O5—C16—H16A109.7
C1—C2—C18121.2 (4)C15—C16—H16A109.7
C1—C2—C3120.8 (3)O5—C16—H16B109.7
C18—C2—C3117.9 (3)C15—C16—H16B109.7
C4—C3—C2111.3 (3)H16A—C16—H16B108.2
C4—C3—C8113.1 (3)O5—C17—H17A109.5
C2—C3—C8109.1 (3)O5—C17—H17B109.5
C4—C3—H3107.7H17A—C17—H17B109.5
C2—C3—H3107.7O5—C17—H17C109.5
C8—C3—H3107.7H17A—C17—H17C109.5
C5—C4—C14120.0 (3)H17B—C17—H17C109.5
C5—C4—C3121.3 (3)O1—C18—O2122.4 (4)
C14—C4—C3118.6 (3)O1—C18—C2126.6 (4)
C4—C5—N1119.3 (4)O2—C18—C2111.0 (3)
C4—C5—C6127.6 (4)O2—C19—C20113.1 (3)
N1—C5—C6113.1 (3)O2—C19—H19A109.0
C5—C6—H6A109.5C20—C19—H19A109.0
C5—C6—H6B109.5O2—C19—H19B109.0
H6A—C6—H6B109.5C20—C19—H19B109.0
C5—C6—H6C109.5H19A—C19—H19B107.8
H6A—C6—H6C109.5C21—C20—C19127.0 (4)
H6B—C6—H6C109.5C21—C20—H20116.5
C1—C7—H7A109.5C19—C20—H20116.5
C1—C7—H7B109.5C20—C21—C22125.9 (4)
H7A—C7—H7B109.5C20—C21—H21117.0
C1—C7—H7C109.5C22—C21—H21117.0
H7A—C7—H7C109.5C27—C22—C23117.9 (4)
H7B—C7—H7C109.5C27—C22—C21122.8 (4)
C9—C8—C13119.3 (3)C23—C22—C21119.2 (4)
C9—C8—C3121.2 (3)C24—C23—C22120.1 (4)
C13—C8—C3119.5 (3)C24—C23—H23120.0
C8—C9—C10119.6 (3)C22—C23—H23120.0
C8—C9—H9120.2C25—C24—C23121.0 (4)
C10—C9—H9120.2C25—C24—H24119.5
C9—C10—C11122.2 (4)C23—C24—H24119.5
C9—C10—N2119.5 (4)C26—C25—C24119.5 (4)
C11—C10—N2118.4 (4)C26—C25—H25120.3
C12—C11—C10118.1 (3)C24—C25—H25120.3
C12—C11—H11121.0C25—C26—C27121.0 (4)
C10—C11—H11121.0C25—C26—H26119.5
C11—C12—C13120.2 (4)C27—C26—H26119.5
C11—C12—H12119.9C26—C27—C22120.6 (4)
C13—C12—H12119.9C26—C27—H27119.7
C8—C13—C12120.6 (3)C22—C27—H27119.7
C8—C13—H13119.7C5—N1—C1123.3 (3)
C12—C13—H13119.7C5—N1—H1A118.3
O3—C14—O4122.4 (4)C1—N1—H1A118.3
O3—C14—C4127.2 (4)O7—N2—O6123.3 (4)
O4—C14—C4110.4 (3)O7—N2—C10118.9 (4)
O4—C15—C16107.6 (3)O6—N2—C10117.7 (4)
O4—C15—H15A110.2C18—O2—C19117.4 (3)
C16—C15—H15A110.2C14—O4—C15117.7 (3)
O4—C15—H15B110.2C16—O5—C17112.5 (3)
C16—C15—H15B110.2
N1—C1—C2—C18177.0 (3)C3—C4—C14—O411.5 (4)
C7—C1—C2—C182.7 (6)O4—C15—C16—O569.3 (4)
N1—C1—C2—C37.2 (5)C1—C2—C18—O15.7 (6)
C7—C1—C2—C3173.1 (3)C3—C2—C18—O1170.2 (4)
C1—C2—C3—C420.8 (4)C1—C2—C18—O2172.2 (3)
C18—C2—C3—C4163.3 (3)C3—C2—C18—O212.0 (4)
C1—C2—C3—C8104.7 (4)O2—C19—C20—C212.9 (7)
C18—C2—C3—C871.2 (4)C19—C20—C21—C22179.9 (4)
C2—C3—C4—C519.5 (4)C20—C21—C22—C273.4 (7)
C8—C3—C4—C5103.8 (4)C20—C21—C22—C23179.8 (4)
C2—C3—C4—C14163.0 (3)C27—C22—C23—C240.6 (6)
C8—C3—C4—C1473.7 (4)C21—C22—C23—C24177.6 (4)
C14—C4—C5—N1178.1 (3)C22—C23—C24—C250.6 (7)
C3—C4—C5—N14.4 (5)C23—C24—C25—C260.1 (7)
C14—C4—C5—C62.6 (6)C24—C25—C26—C270.5 (7)
C3—C4—C5—C6174.9 (3)C25—C26—C27—C220.5 (8)
C4—C3—C8—C9118.3 (4)C23—C22—C27—C260.1 (7)
C2—C3—C8—C9117.3 (4)C21—C22—C27—C26177.0 (4)
C4—C3—C8—C1365.1 (4)C4—C5—N1—C112.2 (5)
C2—C3—C8—C1359.3 (4)C6—C5—N1—C1168.4 (3)
C13—C8—C9—C100.1 (5)C2—C1—N1—C510.7 (5)
C3—C8—C9—C10176.7 (3)C7—C1—N1—C5169.0 (3)
C8—C9—C10—C111.7 (6)C9—C10—N2—O7164.1 (4)
C8—C9—C10—N2176.7 (4)C11—C10—N2—O714.5 (6)
C9—C10—C11—C121.9 (6)C9—C10—N2—O616.0 (6)
N2—C10—C11—C12176.6 (4)C11—C10—N2—O6165.4 (4)
C10—C11—C12—C130.3 (6)O1—C18—O2—C193.5 (5)
C9—C8—C13—C121.7 (5)C2—C18—O2—C19174.4 (3)
C3—C8—C13—C12178.4 (3)C20—C19—O2—C1891.9 (4)
C11—C12—C13—C81.5 (6)O3—C14—O4—C153.6 (5)
C5—C4—C14—O314.1 (6)C4—C14—O4—C15176.5 (3)
C3—C4—C14—O3168.3 (4)C16—C15—O4—C14142.6 (3)
C5—C4—C14—O4166.0 (3)C15—C16—O5—C17176.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O5i0.882.042.925 (4)179
Symmetry code: (i) x+1/2, y, z+1/2.
 

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