The principal structural feature of the title compound, C
20H
21ClN
2O
6, is the dihedral angle of 89.15 (8)° between the two benzene rings of the molecule. The N—C
sp2 bond distance of 1.387 (3) Å is significantly shorter than the N—C
sp3 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
CCDC reference: 613858
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
C20H21ClN2O6 | Z = 2 |
Mr = 420.84 | F(000) = 440 |
Triclinic, P1 | Dx = 1.331 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.0765 (11) Å | Cell parameters from 1951 reflections |
b = 11.0454 (13) Å | θ = 2.4–25.0° |
c = 12.0174 (14) Å | µ = 0.22 mm−1 |
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 tube | 2717 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.115 |
Detector resolution: 10 pixels mm-1 | θmax = 25.2°, θmin = 1.9° |
φ and ω scans | h = −10→10 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −12→13 |
Tmin = 0.885, Tmax = 0.930 | l = −14→11 |
5463 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.189 | H-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 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Cl | 0.93356 (15) | 1.00508 (8) | 0.13524 (8) | 0.1243 (5) | |
O1 | 0.5318 (3) | 0.34678 (19) | 0.10309 (16) | 0.0845 (7) | |
O2 | 0.6216 (3) | 0.22400 (17) | 0.22175 (16) | 0.0710 (6) | |
O3 | 1.0358 (2) | 0.38330 (19) | 0.38547 (15) | 0.0668 (5) | |
O4 | 0.9534 (2) | 0.39161 (16) | 0.18906 (13) | 0.0540 (5) | |
O5 | 0.5615 (2) | 0.6578 (2) | 0.59488 (17) | 0.0745 (6) | |
O6 | 0.3207 (3) | 0.6669 (3) | 0.4953 (2) | 0.1087 (9) | |
N1 | 0.9522 (2) | 0.66038 (18) | 0.36555 (16) | 0.0468 (5) | |
H1N | 0.9762 | 0.6430 | 0.4375 | 0.070* | |
N2 | 0.4562 (3) | 0.6653 (2) | 0.5027 (2) | 0.0588 (6) | |
C1 | 0.7861 (3) | 0.4381 (2) | 0.29155 (18) | 0.0445 (5) | |
H1 | 0.7817 | 0.4422 | 0.3724 | 0.053* | |
C2 | 0.7926 (3) | 0.5714 (2) | 0.27161 (18) | 0.0433 (5) | |
H2 | 0.7901 | 0.5673 | 0.1887 | 0.052* | |
C3 | 0.6458 (3) | 0.6128 (2) | 0.27812 (19) | 0.0434 (5) | |
C4 | 0.6215 (3) | 0.6266 (2) | 0.38694 (19) | 0.0428 (5) | |
H4 | 0.6957 | 0.6121 | 0.4565 | 0.051* | |
C5 | 0.4865 (3) | 0.6618 (2) | 0.3905 (2) | 0.0483 (6) | |
C6 | 0.3757 (3) | 0.6886 (3) | 0.2925 (2) | 0.0615 (7) | |
H6 | 0.2865 | 0.7138 | 0.2982 | 0.074* | |
C7 | 0.4018 (3) | 0.6766 (3) | 0.1854 (2) | 0.0673 (8) | |
H7 | 0.3290 | 0.6938 | 0.1171 | 0.081* | |
C8 | 0.5338 (3) | 0.6396 (2) | 0.1787 (2) | 0.0566 (6) | |
H8 | 0.5490 | 0.6322 | 0.1055 | 0.068* | |
C9 | 1.0072 (3) | 0.7877 (2) | 0.3664 (2) | 0.0458 (6) | |
C10 | 1.1314 (3) | 0.8765 (2) | 0.4765 (2) | 0.0607 (7) | |
H10 | 1.1733 | 0.8505 | 0.5478 | 0.073* | |
C11 | 1.1923 (4) | 1.0037 (3) | 0.4791 (3) | 0.0779 (9) | |
H11 | 1.2748 | 1.0624 | 0.5531 | 0.093* | |
C12 | 1.1342 (4) | 1.0448 (3) | 0.3760 (3) | 0.0801 (9) | |
H12 | 1.1764 | 1.1301 | 0.3785 | 0.096* | |
C13 | 1.0123 (4) | 0.9570 (3) | 0.2693 (2) | 0.0689 (8) | |
C14 | 0.9476 (3) | 0.8293 (2) | 0.2619 (2) | 0.0567 (7) | |
H14 | 0.8647 | 0.7719 | 0.1874 | 0.068* | |
C15 | 0.6321 (3) | 0.3326 (2) | 0.1923 (2) | 0.0533 (6) | |
C16 | 0.4704 (5) | 0.1175 (3) | 0.1397 (4) | 0.1129 (14) | |
H16A | 0.3745 | 0.1487 | 0.1236 | 0.135* | |
H16B | 0.4746 | 0.0840 | 0.0606 | 0.135* | |
C17 | 0.4561 (8) | 0.0195 (5) | 0.1966 (5) | 0.192 (3) | |
H17A | 0.5427 | −0.0193 | 0.2016 | 0.231* | |
H17B | 0.3501 | −0.0450 | 0.1481 | 0.231* | |
H17C | 0.4656 | 0.0554 | 0.2791 | 0.231* | |
C18 | 0.9393 (3) | 0.4019 (2) | 0.2965 (2) | 0.0488 (6) | |
C19 | 1.0984 (3) | 0.3590 (3) | 0.1841 (2) | 0.0587 (7) | |
H19A | 1.1047 | 0.2807 | 0.2082 | 0.070* | |
H19B | 1.1985 | 0.4285 | 0.2411 | 0.070* | |
C20 | 1.0823 (4) | 0.3394 (4) | 0.0539 (3) | 0.0894 (10) | |
H20A | 0.9849 | 0.2686 | −0.0013 | 0.107* | |
H20B | 1.1785 | 0.3202 | 0.0487 | 0.107* | |
H20C | 1.0733 | 0.4166 | 0.0302 | 0.107* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl | 0.1729 (11) | 0.0747 (6) | 0.0699 (6) | −0.0160 (6) | 0.0098 (6) | 0.0412 (5) |
O1 | 0.0991 (16) | 0.0665 (13) | 0.0467 (10) | 0.0024 (11) | −0.0015 (10) | 0.0161 (9) |
O2 | 0.0924 (14) | 0.0439 (10) | 0.0551 (10) | 0.0042 (9) | 0.0172 (10) | 0.0131 (8) |
O3 | 0.0809 (13) | 0.0849 (14) | 0.0422 (9) | 0.0390 (11) | 0.0223 (9) | 0.0270 (9) |
O4 | 0.0685 (11) | 0.0644 (11) | 0.0376 (8) | 0.0267 (9) | 0.0265 (8) | 0.0177 (7) |
O5 | 0.0761 (13) | 0.1076 (17) | 0.0522 (11) | 0.0367 (12) | 0.0327 (10) | 0.0292 (11) |
O6 | 0.0919 (18) | 0.184 (3) | 0.1046 (18) | 0.0757 (19) | 0.0667 (15) | 0.0725 (19) |
N1 | 0.0513 (11) | 0.0478 (11) | 0.0371 (9) | 0.0101 (9) | 0.0156 (8) | 0.0147 (8) |
N2 | 0.0587 (14) | 0.0663 (14) | 0.0624 (14) | 0.0229 (11) | 0.0346 (11) | 0.0203 (11) |
C1 | 0.0600 (14) | 0.0443 (13) | 0.0294 (10) | 0.0122 (11) | 0.0210 (10) | 0.0107 (9) |
C2 | 0.0551 (13) | 0.0435 (12) | 0.0304 (10) | 0.0098 (10) | 0.0190 (10) | 0.0126 (9) |
C3 | 0.0495 (13) | 0.0375 (11) | 0.0372 (11) | 0.0049 (9) | 0.0160 (10) | 0.0113 (9) |
C4 | 0.0480 (13) | 0.0402 (12) | 0.0351 (11) | 0.0086 (10) | 0.0140 (9) | 0.0121 (9) |
C5 | 0.0490 (14) | 0.0440 (13) | 0.0499 (13) | 0.0074 (10) | 0.0208 (11) | 0.0167 (10) |
C6 | 0.0564 (16) | 0.0664 (17) | 0.0689 (17) | 0.0240 (13) | 0.0264 (13) | 0.0295 (14) |
C7 | 0.0663 (18) | 0.081 (2) | 0.0578 (15) | 0.0279 (15) | 0.0176 (13) | 0.0374 (14) |
C8 | 0.0650 (16) | 0.0631 (16) | 0.0447 (13) | 0.0189 (13) | 0.0216 (12) | 0.0259 (12) |
C9 | 0.0493 (13) | 0.0469 (13) | 0.0425 (12) | 0.0094 (10) | 0.0246 (10) | 0.0108 (10) |
C10 | 0.0615 (16) | 0.0602 (16) | 0.0452 (13) | 0.0066 (12) | 0.0130 (11) | 0.0144 (12) |
C11 | 0.080 (2) | 0.0578 (17) | 0.0590 (16) | −0.0059 (14) | 0.0099 (14) | 0.0056 (13) |
C12 | 0.093 (2) | 0.0559 (17) | 0.0672 (18) | −0.0061 (15) | 0.0226 (16) | 0.0178 (14) |
C13 | 0.086 (2) | 0.0573 (16) | 0.0510 (14) | 0.0017 (14) | 0.0247 (14) | 0.0187 (12) |
C14 | 0.0693 (16) | 0.0508 (14) | 0.0393 (12) | 0.0010 (12) | 0.0216 (11) | 0.0108 (11) |
C15 | 0.0708 (16) | 0.0519 (14) | 0.0343 (12) | 0.0127 (12) | 0.0223 (12) | 0.0122 (10) |
C16 | 0.125 (3) | 0.055 (2) | 0.089 (2) | −0.020 (2) | 0.002 (2) | 0.0080 (18) |
C17 | 0.205 (6) | 0.114 (4) | 0.132 (4) | −0.074 (4) | −0.005 (4) | 0.046 (3) |
C18 | 0.0683 (16) | 0.0432 (12) | 0.0331 (11) | 0.0136 (11) | 0.0205 (11) | 0.0127 (9) |
C19 | 0.0671 (16) | 0.0570 (15) | 0.0573 (14) | 0.0231 (13) | 0.0299 (13) | 0.0158 (12) |
C20 | 0.099 (2) | 0.124 (3) | 0.0698 (19) | 0.054 (2) | 0.0507 (19) | 0.0306 (19) |
Geometric parameters (Å, º) top
Cl—C13 | 1.743 (3) | C7—C8 | 1.367 (4) |
O1—C15 | 1.191 (3) | C7—H7 | 0.9300 |
O2—C15 | 1.308 (3) | C8—H8 | 0.9300 |
O2—C16 | 1.463 (4) | C9—C14 | 1.382 (3) |
O3—C18 | 1.197 (3) | C9—C10 | 1.394 (3) |
O4—C18 | 1.329 (3) | C10—C11 | 1.388 (4) |
O4—C19 | 1.453 (3) | C10—H10 | 0.9300 |
O5—N2 | 1.203 (3) | C11—C12 | 1.364 (4) |
O6—N2 | 1.205 (3) | C11—H11 | 0.9300 |
N1—C2 | 1.461 (3) | C12—C13 | 1.363 (4) |
N1—C9 | 1.387 (3) | C12—H12 | 0.9300 |
N1—H1N | 0.8807 | C13—C14 | 1.383 (4) |
N2—C5 | 1.466 (3) | C14—H14 | 0.9300 |
C1—C18 | 1.509 (3) | C16—C17 | 1.394 (6) |
C1—C15 | 1.521 (3) | C16—H16A | 0.9700 |
C1—C2 | 1.529 (3) | C16—H16B | 0.9700 |
C1—H1 | 0.9800 | C17—H17A | 0.9600 |
C2—C3 | 1.519 (3) | C17—H17B | 0.9600 |
C2—H2 | 0.9800 | C17—H17C | 0.9600 |
C3—C8 | 1.388 (3) | C19—C20 | 1.486 (4) |
C3—C4 | 1.389 (3) | C19—H19A | 0.9700 |
C4—C5 | 1.373 (3) | C19—H19B | 0.9700 |
C4—H4 | 0.9300 | C20—H20A | 0.9600 |
C5—C6 | 1.372 (3) | C20—H20B | 0.9600 |
C6—C7 | 1.379 (4) | C20—H20C | 0.9600 |
C6—H6 | 0.9300 | | |
| | | |
C15—O2—C16 | 115.4 (2) | C9—C10—H10 | 120.1 |
C18—O4—C19 | 116.32 (19) | C12—C11—C10 | 121.6 (3) |
C9—N1—C2 | 122.01 (18) | C12—C11—H11 | 119.2 |
C9—N1—H1N | 118.6 | C10—C11—H11 | 119.2 |
C2—N1—H1N | 110.6 | C13—C12—C11 | 117.9 (3) |
O5—N2—O6 | 122.6 (2) | C13—C12—H12 | 121.1 |
O5—N2—C5 | 119.6 (2) | C11—C12—H12 | 121.1 |
O6—N2—C5 | 117.6 (2) | C12—C13—C14 | 122.6 (3) |
C18—C1—C15 | 109.68 (18) | C12—C13—Cl | 119.6 (2) |
C18—C1—C2 | 111.83 (19) | C14—C13—Cl | 117.8 (2) |
C15—C1—C2 | 112.32 (18) | C9—C14—C13 | 119.4 (2) |
C18—C1—H1 | 107.6 | C9—C14—H14 | 120.3 |
C15—C1—H1 | 107.6 | C13—C14—H14 | 120.3 |
C2—C1—H1 | 107.6 | O1—C15—O2 | 124.5 (2) |
N1—C2—C3 | 112.99 (16) | O1—C15—C1 | 125.5 (2) |
N1—C2—C1 | 106.49 (17) | O2—C15—C1 | 110.0 (2) |
C3—C2—C1 | 111.74 (18) | C17—C16—O2 | 109.5 (4) |
N1—C2—H2 | 108.5 | C17—C16—H16A | 109.8 |
C3—C2—H2 | 108.5 | O2—C16—H16A | 109.8 |
C1—C2—H2 | 108.5 | C17—C16—H16B | 109.8 |
C8—C3—C4 | 117.8 (2) | O2—C16—H16B | 109.8 |
C8—C3—C2 | 122.31 (19) | H16A—C16—H16B | 108.2 |
C4—C3—C2 | 119.87 (19) | C16—C17—H17A | 109.5 |
C5—C4—C3 | 119.1 (2) | C16—C17—H17B | 109.5 |
C5—C4—H4 | 120.4 | H17A—C17—H17B | 109.5 |
C3—C4—H4 | 120.4 | C16—C17—H17C | 109.5 |
C6—C5—C4 | 123.2 (2) | H17A—C17—H17C | 109.5 |
C6—C5—N2 | 118.8 (2) | H17B—C17—H17C | 109.5 |
C4—C5—N2 | 118.0 (2) | O3—C18—O4 | 123.8 (2) |
C5—C6—C7 | 117.4 (2) | O3—C18—C1 | 124.5 (2) |
C5—C6—H6 | 121.3 | O4—C18—C1 | 111.68 (19) |
C7—C6—H6 | 121.3 | O4—C19—C20 | 107.9 (2) |
C8—C7—C6 | 120.5 (2) | O4—C19—H19A | 110.1 |
C8—C7—H7 | 119.7 | C20—C19—H19A | 110.1 |
C6—C7—H7 | 119.7 | O4—C19—H19B | 110.1 |
C7—C8—C3 | 121.9 (2) | C20—C19—H19B | 110.1 |
C7—C8—H8 | 119.0 | H19A—C19—H19B | 108.4 |
C3—C8—H8 | 119.0 | C19—C20—H20A | 109.5 |
C14—C9—N1 | 122.8 (2) | C19—C20—H20B | 109.5 |
C14—C9—C10 | 118.7 (2) | H20A—C20—H20B | 109.5 |
N1—C9—C10 | 118.5 (2) | C19—C20—H20C | 109.5 |
C11—C10—C9 | 119.8 (3) | H20A—C20—H20C | 109.5 |
C11—C10—H10 | 120.1 | H20B—C20—H20C | 109.5 |
| | | |
C9—N1—C2—C3 | −63.8 (2) | C2—N1—C9—C10 | 160.5 (2) |
C9—N1—C2—C1 | 173.17 (17) | C14—C9—C10—C11 | 0.0 (4) |
C18—C1—C2—N1 | −51.1 (2) | N1—C9—C10—C11 | 178.2 (2) |
C15—C1—C2—N1 | −174.95 (16) | C9—C10—C11—C12 | −0.3 (5) |
C18—C1—C2—C3 | −174.95 (16) | C10—C11—C12—C13 | 0.5 (5) |
C15—C1—C2—C3 | 61.2 (2) | C11—C12—C13—C14 | −0.5 (5) |
N1—C2—C3—C8 | 119.8 (2) | C11—C12—C13—Cl | 179.8 (3) |
C1—C2—C3—C8 | −120.2 (2) | N1—C9—C14—C13 | −178.0 (2) |
N1—C2—C3—C4 | −59.4 (3) | C10—C9—C14—C13 | 0.0 (4) |
C1—C2—C3—C4 | 60.7 (2) | C12—C13—C14—C9 | 0.2 (4) |
C8—C3—C4—C5 | 2.0 (3) | Cl—C13—C14—C9 | 180.0 (2) |
C2—C3—C4—C5 | −178.85 (19) | C16—O2—C15—O1 | −3.0 (4) |
C3—C4—C5—C6 | −2.2 (3) | C16—O2—C15—C1 | 174.5 (3) |
C3—C4—C5—N2 | 175.09 (19) | C18—C1—C15—O1 | −119.8 (3) |
O5—N2—C5—C6 | −170.9 (2) | C2—C1—C15—O1 | 5.2 (3) |
O6—N2—C5—C6 | 14.0 (4) | C18—C1—C15—O2 | 62.7 (2) |
O5—N2—C5—C4 | 11.7 (3) | C2—C1—C15—O2 | −172.24 (19) |
O6—N2—C5—C4 | −163.4 (2) | C15—O2—C16—C17 | −166.0 (4) |
C4—C5—C6—C7 | 1.2 (4) | C19—O4—C18—O3 | −1.7 (4) |
N2—C5—C6—C7 | −176.0 (2) | C19—O4—C18—C1 | 179.06 (18) |
C5—C6—C7—C8 | −0.1 (4) | C15—C1—C18—O3 | −117.3 (3) |
C6—C7—C8—C3 | 0.0 (4) | C2—C1—C18—O3 | 117.4 (2) |
C4—C3—C8—C7 | −1.0 (4) | C15—C1—C18—O4 | 62.0 (2) |
C2—C3—C8—C7 | 179.9 (2) | C2—C1—C18—O4 | −63.3 (2) |
C2—N1—C9—C14 | −21.4 (3) | C18—O4—C19—C20 | 174.5 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O3i | 0.88 | 2.24 | 3.088 (3) | 162 |
C1—H1···O6ii | 0.98 | 2.49 | 3.363 (4) | 149 |
C4—H4···O3i | 0.93 | 2.47 | 3.353 (3) | 159 |
C8—H8···O1iii | 0.93 | 2.42 | 3.258 (3) | 151 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+1, −z. |