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The principal structural feature of the title compound, C20H21ClN2O6, is the dihedral angle of 89.15 (8)° between the two benzene rings of the mol­ecule. The N—Csp2 bond distance of 1.387 (3) Å is significantly shorter than the N—Csp3 bond distance of 1.461 (3) Å. Classical N—H...O and weak C—H...O hydrogen bonding occurs in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806020009/xu2045sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806020009/xu2045Isup2.hkl
Contains datablock I

CCDC reference: 613858

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.064
  • wR factor = 0.189
  • Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.49 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.53 Ratio
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.115 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12 PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C18 .. 5.05 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16 PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C16 - C17 ... 1.39 Ang.
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXTL.

Diethyl 2-[(3-chlorophenylamino)(3-nitrophenyl)methyl]malonate top
Crystal data top
C20H21ClN2O6Z = 2
Mr = 420.84F(000) = 440
Triclinic, P1Dx = 1.331 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.0765 (11) ÅCell parameters from 1951 reflections
b = 11.0454 (13) Åθ = 2.4–25.0°
c = 12.0174 (14) ŵ = 0.22 mm1
α = 101.010 (2)°T = 293 K
β = 111.271 (2)°Block, green
γ = 102.040 (2)°0.51 × 0.50 × 0.32 mm
V = 1050.0 (2) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
3748 independent reflections
Radiation source: fine-focus sealed tube2717 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.115
Detector resolution: 10 pixels mm-1θmax = 25.2°, θmin = 1.9°
φ and ω scansh = 1010
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1213
Tmin = 0.885, Tmax = 0.930l = 1411
5463 measured reflections
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)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.189H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.1023P)2]
where P = (Fo2 + 2Fc2)/3
3748 reflections(Δ/σ)max = 0.002
264 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.31 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
Cl0.93356 (15)1.00508 (8)0.13524 (8)0.1243 (5)
O10.5318 (3)0.34678 (19)0.10309 (16)0.0845 (7)
O20.6216 (3)0.22400 (17)0.22175 (16)0.0710 (6)
O31.0358 (2)0.38330 (19)0.38547 (15)0.0668 (5)
O40.9534 (2)0.39161 (16)0.18906 (13)0.0540 (5)
O50.5615 (2)0.6578 (2)0.59488 (17)0.0745 (6)
O60.3207 (3)0.6669 (3)0.4953 (2)0.1087 (9)
N10.9522 (2)0.66038 (18)0.36555 (16)0.0468 (5)
H1N0.97620.64300.43750.070*
N20.4562 (3)0.6653 (2)0.5027 (2)0.0588 (6)
C10.7861 (3)0.4381 (2)0.29155 (18)0.0445 (5)
H10.78170.44220.37240.053*
C20.7926 (3)0.5714 (2)0.27161 (18)0.0433 (5)
H20.79010.56730.18870.052*
C30.6458 (3)0.6128 (2)0.27812 (19)0.0434 (5)
C40.6215 (3)0.6266 (2)0.38694 (19)0.0428 (5)
H40.69570.61210.45650.051*
C50.4865 (3)0.6618 (2)0.3905 (2)0.0483 (6)
C60.3757 (3)0.6886 (3)0.2925 (2)0.0615 (7)
H60.28650.71380.29820.074*
C70.4018 (3)0.6766 (3)0.1854 (2)0.0673 (8)
H70.32900.69380.11710.081*
C80.5338 (3)0.6396 (2)0.1787 (2)0.0566 (6)
H80.54900.63220.10550.068*
C91.0072 (3)0.7877 (2)0.3664 (2)0.0458 (6)
C101.1314 (3)0.8765 (2)0.4765 (2)0.0607 (7)
H101.17330.85050.54780.073*
C111.1923 (4)1.0037 (3)0.4791 (3)0.0779 (9)
H111.27481.06240.55310.093*
C121.1342 (4)1.0448 (3)0.3760 (3)0.0801 (9)
H121.17641.13010.37850.096*
C131.0123 (4)0.9570 (3)0.2693 (2)0.0689 (8)
C140.9476 (3)0.8293 (2)0.2619 (2)0.0567 (7)
H140.86470.77190.18740.068*
C150.6321 (3)0.3326 (2)0.1923 (2)0.0533 (6)
C160.4704 (5)0.1175 (3)0.1397 (4)0.1129 (14)
H16A0.37450.14870.12360.135*
H16B0.47460.08400.06060.135*
C170.4561 (8)0.0195 (5)0.1966 (5)0.192 (3)
H17A0.54270.01930.20160.231*
H17B0.35010.04500.14810.231*
H17C0.46560.05540.27910.231*
C180.9393 (3)0.4019 (2)0.2965 (2)0.0488 (6)
C191.0984 (3)0.3590 (3)0.1841 (2)0.0587 (7)
H19A1.10470.28070.20820.070*
H19B1.19850.42850.24110.070*
C201.0823 (4)0.3394 (4)0.0539 (3)0.0894 (10)
H20A0.98490.26860.00130.107*
H20B1.17850.32020.04870.107*
H20C1.07330.41660.03020.107*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.1729 (11)0.0747 (6)0.0699 (6)0.0160 (6)0.0098 (6)0.0412 (5)
O10.0991 (16)0.0665 (13)0.0467 (10)0.0024 (11)0.0015 (10)0.0161 (9)
O20.0924 (14)0.0439 (10)0.0551 (10)0.0042 (9)0.0172 (10)0.0131 (8)
O30.0809 (13)0.0849 (14)0.0422 (9)0.0390 (11)0.0223 (9)0.0270 (9)
O40.0685 (11)0.0644 (11)0.0376 (8)0.0267 (9)0.0265 (8)0.0177 (7)
O50.0761 (13)0.1076 (17)0.0522 (11)0.0367 (12)0.0327 (10)0.0292 (11)
O60.0919 (18)0.184 (3)0.1046 (18)0.0757 (19)0.0667 (15)0.0725 (19)
N10.0513 (11)0.0478 (11)0.0371 (9)0.0101 (9)0.0156 (8)0.0147 (8)
N20.0587 (14)0.0663 (14)0.0624 (14)0.0229 (11)0.0346 (11)0.0203 (11)
C10.0600 (14)0.0443 (13)0.0294 (10)0.0122 (11)0.0210 (10)0.0107 (9)
C20.0551 (13)0.0435 (12)0.0304 (10)0.0098 (10)0.0190 (10)0.0126 (9)
C30.0495 (13)0.0375 (11)0.0372 (11)0.0049 (9)0.0160 (10)0.0113 (9)
C40.0480 (13)0.0402 (12)0.0351 (11)0.0086 (10)0.0140 (9)0.0121 (9)
C50.0490 (14)0.0440 (13)0.0499 (13)0.0074 (10)0.0208 (11)0.0167 (10)
C60.0564 (16)0.0664 (17)0.0689 (17)0.0240 (13)0.0264 (13)0.0295 (14)
C70.0663 (18)0.081 (2)0.0578 (15)0.0279 (15)0.0176 (13)0.0374 (14)
C80.0650 (16)0.0631 (16)0.0447 (13)0.0189 (13)0.0216 (12)0.0259 (12)
C90.0493 (13)0.0469 (13)0.0425 (12)0.0094 (10)0.0246 (10)0.0108 (10)
C100.0615 (16)0.0602 (16)0.0452 (13)0.0066 (12)0.0130 (11)0.0144 (12)
C110.080 (2)0.0578 (17)0.0590 (16)0.0059 (14)0.0099 (14)0.0056 (13)
C120.093 (2)0.0559 (17)0.0672 (18)0.0061 (15)0.0226 (16)0.0178 (14)
C130.086 (2)0.0573 (16)0.0510 (14)0.0017 (14)0.0247 (14)0.0187 (12)
C140.0693 (16)0.0508 (14)0.0393 (12)0.0010 (12)0.0216 (11)0.0108 (11)
C150.0708 (16)0.0519 (14)0.0343 (12)0.0127 (12)0.0223 (12)0.0122 (10)
C160.125 (3)0.055 (2)0.089 (2)0.020 (2)0.002 (2)0.0080 (18)
C170.205 (6)0.114 (4)0.132 (4)0.074 (4)0.005 (4)0.046 (3)
C180.0683 (16)0.0432 (12)0.0331 (11)0.0136 (11)0.0205 (11)0.0127 (9)
C190.0671 (16)0.0570 (15)0.0573 (14)0.0231 (13)0.0299 (13)0.0158 (12)
C200.099 (2)0.124 (3)0.0698 (19)0.054 (2)0.0507 (19)0.0306 (19)
Geometric parameters (Å, º) top
Cl—C131.743 (3)C7—C81.367 (4)
O1—C151.191 (3)C7—H70.9300
O2—C151.308 (3)C8—H80.9300
O2—C161.463 (4)C9—C141.382 (3)
O3—C181.197 (3)C9—C101.394 (3)
O4—C181.329 (3)C10—C111.388 (4)
O4—C191.453 (3)C10—H100.9300
O5—N21.203 (3)C11—C121.364 (4)
O6—N21.205 (3)C11—H110.9300
N1—C21.461 (3)C12—C131.363 (4)
N1—C91.387 (3)C12—H120.9300
N1—H1N0.8807C13—C141.383 (4)
N2—C51.466 (3)C14—H140.9300
C1—C181.509 (3)C16—C171.394 (6)
C1—C151.521 (3)C16—H16A0.9700
C1—C21.529 (3)C16—H16B0.9700
C1—H10.9800C17—H17A0.9600
C2—C31.519 (3)C17—H17B0.9600
C2—H20.9800C17—H17C0.9600
C3—C81.388 (3)C19—C201.486 (4)
C3—C41.389 (3)C19—H19A0.9700
C4—C51.373 (3)C19—H19B0.9700
C4—H40.9300C20—H20A0.9600
C5—C61.372 (3)C20—H20B0.9600
C6—C71.379 (4)C20—H20C0.9600
C6—H60.9300
C15—O2—C16115.4 (2)C9—C10—H10120.1
C18—O4—C19116.32 (19)C12—C11—C10121.6 (3)
C9—N1—C2122.01 (18)C12—C11—H11119.2
C9—N1—H1N118.6C10—C11—H11119.2
C2—N1—H1N110.6C13—C12—C11117.9 (3)
O5—N2—O6122.6 (2)C13—C12—H12121.1
O5—N2—C5119.6 (2)C11—C12—H12121.1
O6—N2—C5117.6 (2)C12—C13—C14122.6 (3)
C18—C1—C15109.68 (18)C12—C13—Cl119.6 (2)
C18—C1—C2111.83 (19)C14—C13—Cl117.8 (2)
C15—C1—C2112.32 (18)C9—C14—C13119.4 (2)
C18—C1—H1107.6C9—C14—H14120.3
C15—C1—H1107.6C13—C14—H14120.3
C2—C1—H1107.6O1—C15—O2124.5 (2)
N1—C2—C3112.99 (16)O1—C15—C1125.5 (2)
N1—C2—C1106.49 (17)O2—C15—C1110.0 (2)
C3—C2—C1111.74 (18)C17—C16—O2109.5 (4)
N1—C2—H2108.5C17—C16—H16A109.8
C3—C2—H2108.5O2—C16—H16A109.8
C1—C2—H2108.5C17—C16—H16B109.8
C8—C3—C4117.8 (2)O2—C16—H16B109.8
C8—C3—C2122.31 (19)H16A—C16—H16B108.2
C4—C3—C2119.87 (19)C16—C17—H17A109.5
C5—C4—C3119.1 (2)C16—C17—H17B109.5
C5—C4—H4120.4H17A—C17—H17B109.5
C3—C4—H4120.4C16—C17—H17C109.5
C6—C5—C4123.2 (2)H17A—C17—H17C109.5
C6—C5—N2118.8 (2)H17B—C17—H17C109.5
C4—C5—N2118.0 (2)O3—C18—O4123.8 (2)
C5—C6—C7117.4 (2)O3—C18—C1124.5 (2)
C5—C6—H6121.3O4—C18—C1111.68 (19)
C7—C6—H6121.3O4—C19—C20107.9 (2)
C8—C7—C6120.5 (2)O4—C19—H19A110.1
C8—C7—H7119.7C20—C19—H19A110.1
C6—C7—H7119.7O4—C19—H19B110.1
C7—C8—C3121.9 (2)C20—C19—H19B110.1
C7—C8—H8119.0H19A—C19—H19B108.4
C3—C8—H8119.0C19—C20—H20A109.5
C14—C9—N1122.8 (2)C19—C20—H20B109.5
C14—C9—C10118.7 (2)H20A—C20—H20B109.5
N1—C9—C10118.5 (2)C19—C20—H20C109.5
C11—C10—C9119.8 (3)H20A—C20—H20C109.5
C11—C10—H10120.1H20B—C20—H20C109.5
C9—N1—C2—C363.8 (2)C2—N1—C9—C10160.5 (2)
C9—N1—C2—C1173.17 (17)C14—C9—C10—C110.0 (4)
C18—C1—C2—N151.1 (2)N1—C9—C10—C11178.2 (2)
C15—C1—C2—N1174.95 (16)C9—C10—C11—C120.3 (5)
C18—C1—C2—C3174.95 (16)C10—C11—C12—C130.5 (5)
C15—C1—C2—C361.2 (2)C11—C12—C13—C140.5 (5)
N1—C2—C3—C8119.8 (2)C11—C12—C13—Cl179.8 (3)
C1—C2—C3—C8120.2 (2)N1—C9—C14—C13178.0 (2)
N1—C2—C3—C459.4 (3)C10—C9—C14—C130.0 (4)
C1—C2—C3—C460.7 (2)C12—C13—C14—C90.2 (4)
C8—C3—C4—C52.0 (3)Cl—C13—C14—C9180.0 (2)
C2—C3—C4—C5178.85 (19)C16—O2—C15—O13.0 (4)
C3—C4—C5—C62.2 (3)C16—O2—C15—C1174.5 (3)
C3—C4—C5—N2175.09 (19)C18—C1—C15—O1119.8 (3)
O5—N2—C5—C6170.9 (2)C2—C1—C15—O15.2 (3)
O6—N2—C5—C614.0 (4)C18—C1—C15—O262.7 (2)
O5—N2—C5—C411.7 (3)C2—C1—C15—O2172.24 (19)
O6—N2—C5—C4163.4 (2)C15—O2—C16—C17166.0 (4)
C4—C5—C6—C71.2 (4)C19—O4—C18—O31.7 (4)
N2—C5—C6—C7176.0 (2)C19—O4—C18—C1179.06 (18)
C5—C6—C7—C80.1 (4)C15—C1—C18—O3117.3 (3)
C6—C7—C8—C30.0 (4)C2—C1—C18—O3117.4 (2)
C4—C3—C8—C71.0 (4)C15—C1—C18—O462.0 (2)
C2—C3—C8—C7179.9 (2)C2—C1—C18—O463.3 (2)
C2—N1—C9—C1421.4 (3)C18—O4—C19—C20174.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O3i0.882.243.088 (3)162
C1—H1···O6ii0.982.493.363 (4)149
C4—H4···O3i0.932.473.353 (3)159
C8—H8···O1iii0.932.423.258 (3)151
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+1, y+1, z+1; (iii) x+1, y+1, z.
 

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