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The title compound, C
19H
20N
4O
2, which is a key intermediate in the synthesis of natural products, has been synthesized by the reaction of alkenyl(phenyl)iodonium salts with benzotriazole. The keto O atom of the ethoxycarbonyl group is involved in an intramolecular hydrogen bond. In addition to the N—H
O intramolecular hydrogen bond, there are intra- and intermolecular N—H
O, C—H
N and C—H
π weaker interactions in the crystal structure.
Supporting information
CCDC reference: 242334
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.042
- wR factor = 0.051
- Data-to-parameter ratio = 10.6
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT391_ALERT_3_B Deviating Methyl C12 H-C-H Bond Angle ...... 99.16 Deg.
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C16
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C14
PLAT390_ALERT_3_C Deviating Methyl C12 X-C-H Bond Angle ...... 118.25 Deg.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3 .. N3 .. 2.68 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H17 .. N1 .. 2.69 Ang.
PLAT716_ALERT_1_C H...A Unknown or Inconsistent Label .......... C1G
H19 C1G
PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... C1G
C19 C1G
PLAT718_ALERT_1_C D-H..A Unknown or Inconsistent Label .......... C1G
C19 H19 C1G
Alert level G
GOODF01_ALERT_1_G _refine_ls_goodness_of_fit_obs is an old dataname which has
been superseded by _refine_ls_goodness_of_fit_ref
RFACG01_ALERT_3_G _refine_ls_R_factor_obs is an old dataname which has been
superseded by _refine_ls_R_factor_gt
RFACR01_ALERT_3_G _refine_ls_wR_factor_obs is an old dataname which has been
superseded by _refine_ls_wR_factor_ref
SHFSU01_ALERT_2_G _refine_ls_shift/esd_max is an old dataname which has been
superseded by _refine_ls_shift/su_max
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
4 ALERT level G = General alerts; check
4 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
4 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1992); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: PROCESS in TEXSAN (Molecular Structure Corporation, 1992); program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: LS in TEXSAN; software used to prepare material for publication: FINISH in TEXSAN.
(
E)-1-[1-ethoxycarbonyl-2(
N-benzylamino)-1-propenyl]benzotriazole.
top
Crystal data top
C19H20N4O2 | F(000) = 712.00 |
Mr = 336.39 | Dx = 1.241 Mg m−3 |
Monoclinic, P2/c | Mo Kα radiation, λ = 0.7107 Å |
a = 13.071 (3) Å | Cell parameters from 20 reflections |
b = 8.360 (1) Å | θ = 19.4–21.6° |
c = 17.418 (4) Å | µ = 0.08 mm−1 |
β = 109.01 (2)° | T = 293 K |
V = 1799.7 (7) Å3 | Prismatic, colorless |
Z = 4 | 0.30 × 0.30 × 0.20 mm |
Data collection top
Rigaku AFC-7R diffractometer | Rint = 0.083 |
Radiation source: X-ray tube | θmax = 27.5° |
Graphite monochromator | h = 0→15 |
ω/2θ scans | k = 0→10 |
4128 measured reflections | l = −21→19 |
3976 independent reflections | 3 standard reflections every 200 reflections |
3791 reflections with I > 2.5σ(I) | intensity decay: −0.7% |
Refinement top
Refinement on F | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | Weighting scheme based on measured s.u.'s |
R[F2 > 2σ(F2)] = 0.042 | (Δ/σ)max = 0.001 |
wR(F2) = 0.0510 | Δρmax = 0.15 e Å−3 |
2395 reflections | Δρmin = −0.16 e Å−3 |
227 parameters | Extinction correction: Zachariasen_type_2_Gaussian_isotropic |
0 restraints | Extinction coefficient: 35.72402 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.52812 (9) | 0.0699 (1) | 0.66653 (7) | 0.0587 | |
O2 | 0.58444 (9) | 0.1574 (1) | 0.56502 (7) | 0.0562 | |
N1 | 0.6768 (1) | −0.0707 (2) | 0.79173 (9) | 0.0586 | |
N2 | 0.7845 (1) | 0.0457 (2) | 0.63105 (8) | 0.0552 | |
N3 | 0.8084 (1) | −0.0757 (2) | 0.5873 (1) | 0.0688 | |
N4 | 0.8839 (1) | −0.0284 (2) | 0.5590 (1) | 0.0755 | |
C1 | 0.7428 (1) | −0.0508 (2) | 0.7479 (1) | 0.0525 | |
C2 | 0.7085 (1) | 0.0245 (2) | 0.6736 (1) | 0.0512 | |
C3 | 0.6004 (1) | 0.0837 (2) | 0.6365 (1) | 0.0492 | |
C4 | 0.8564 (2) | −0.1127 (3) | 0.7831 (1) | 0.0752 | |
C5 | 0.9104 (1) | 0.1272 (3) | 0.5840 (1) | 0.0613 | |
C6 | 0.9861 (2) | 0.2309 (3) | 0.5697 (1) | 0.0804 | |
C7 | 0.9926 (2) | 0.3791 (4) | 0.6016 (1) | 0.0900 | |
C8 | 0.9269 (2) | 0.4282 (3) | 0.6467 (1) | 0.0927 | |
C9 | 0.8532 (2) | 0.3268 (3) | 0.6621 (1) | 0.0766 | |
C10 | 0.8470 (1) | 0.1749 (2) | 0.6299 (1) | 0.0554 | |
C11 | 0.4773 (1) | 0.2260 (2) | 0.5282 (1) | 0.0612 | |
C12 | 0.4735 (2) | 0.3020 (3) | 0.4497 (1) | 0.0683 | |
C13 | 0.7030 (1) | −0.1536 (2) | 0.8692 (1) | 0.0592 | |
C14 | 0.7000 (1) | −0.3339 (2) | 0.8628 (1) | 0.0529 | |
C15 | 0.6521 (2) | −0.4136 (3) | 0.7908 (1) | 0.0845 | |
C16 | 0.6514 (3) | −0.5806 (4) | 0.7904 (2) | 0.1152 | |
C17 | 0.6976 (3) | −0.6640 (3) | 0.8599 (3) | 0.1093 | |
C18 | 0.7442 (2) | −0.5863 (3) | 0.9305 (2) | 0.0892 | |
C19 | 0.7452 (1) | −0.4229 (2) | 0.9322 (1) | 0.0666 | |
H1 | 0.8548 | −0.2266 | 0.7862 | 0.1481* | |
H2 | 0.8884 | −0.0702 | 0.8360 | 0.1815* | |
H3 | 0.8971 | −0.0819 | 0.7495 | 0.1204* | |
H4 | 1.0269 | 0.1970 | 0.5377 | 0.0796* | |
H5 | 1.0399 | 0.4580 | 0.5910 | 0.0995* | |
H6 | 0.9350 | 0.5378 | 0.6647 | 0.1071* | |
H7 | 0.8095 | 0.3612 | 0.6912 | 0.0912* | |
H8 | 0.4593 | 0.3035 | 0.5680 | 0.0746* | |
H9 | 0.4224 | 0.1382 | 0.5211 | 0.0732* | |
H10 | 0.5295 | 0.3826 | 0.4553 | 0.1058* | |
H11 | 0.4037 | 0.3534 | 0.4252 | 0.0984* | |
H12 | 0.4889 | 0.2261 | 0.4028 | 0.1203* | |
H13 | 0.6500 | −0.1199 | 0.8947 | 0.0744* | |
H14 | 0.7766 | −0.1165 | 0.9090 | 0.0664* | |
H15 | 0.6157 | −0.3500 | 0.7416 | 0.1074* | |
H16 | 0.6166 | −0.6350 | 0.7384 | 0.1378* | |
H17 | 0.6965 | −0.7763 | 0.8573 | 0.1198* | |
H18 | 0.7772 | −0.6471 | 0.9809 | 0.1087* | |
H19 | 0.7784 | −0.3626 | 0.9826 | 0.0856* | |
H20 | 0.6077 | −0.0366 | 0.7691 | 0.0687* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0501 (7) | 0.0695 (8) | 0.0637 (7) | 0.0019 (6) | 0.0285 (6) | 0.0023 (6) |
O2 | 0.0483 (7) | 0.0652 (8) | 0.0593 (7) | 0.0046 (6) | 0.0234 (6) | 0.0051 (6) |
N1 | 0.0556 (9) | 0.0637 (10) | 0.0600 (9) | 0.0036 (8) | 0.0236 (8) | 0.0068 (8) |
N2 | 0.0467 (8) | 0.0658 (10) | 0.0573 (9) | −0.0013 (7) | 0.0227 (7) | −0.0046 (8) |
N3 | 0.064 (1) | 0.075 (1) | 0.075 (1) | 0.0093 (9) | 0.0341 (9) | −0.0055 (9) |
N4 | 0.067 (1) | 0.092 (1) | 0.079 (1) | 0.0151 (10) | 0.0396 (9) | 0.003 (1) |
C1 | 0.0476 (9) | 0.053 (1) | 0.059 (1) | −0.0060 (8) | 0.0191 (8) | −0.0060 (9) |
C2 | 0.0442 (9) | 0.057 (1) | 0.0562 (10) | −0.0038 (8) | 0.0221 (8) | −0.0031 (9) |
C3 | 0.050 (1) | 0.0487 (10) | 0.0532 (10) | −0.0049 (8) | 0.0224 (8) | −0.0072 (8) |
C4 | 0.051 (1) | 0.096 (2) | 0.077 (1) | 0.004 (1) | 0.0174 (10) | 0.006 (1) |
C5 | 0.0421 (10) | 0.089 (1) | 0.054 (1) | 0.0063 (10) | 0.0173 (8) | 0.009 (1) |
C6 | 0.052 (1) | 0.124 (2) | 0.072 (1) | 0.003 (1) | 0.030 (1) | 0.014 (1) |
C7 | 0.068 (1) | 0.124 (2) | 0.080 (2) | −0.032 (1) | 0.028 (1) | 0.005 (2) |
C8 | 0.093 (2) | 0.103 (2) | 0.087 (2) | −0.043 (1) | 0.036 (1) | −0.021 (1) |
C9 | 0.075 (1) | 0.094 (2) | 0.068 (1) | −0.026 (1) | 0.033 (1) | −0.020 (1) |
C10 | 0.0419 (9) | 0.076 (1) | 0.0482 (10) | −0.0062 (9) | 0.0145 (8) | −0.0006 (9) |
C11 | 0.052 (1) | 0.069 (1) | 0.066 (1) | 0.0076 (9) | 0.0232 (9) | 0.0040 (10) |
C12 | 0.069 (1) | 0.075 (1) | 0.062 (1) | 0.006 (1) | 0.0229 (10) | 0.004 (1) |
C13 | 0.072 (1) | 0.056 (1) | 0.052 (1) | −0.0015 (9) | 0.0242 (9) | −0.0023 (9) |
C14 | 0.0516 (10) | 0.054 (1) | 0.060 (1) | −0.0055 (8) | 0.0276 (9) | −0.0090 (9) |
C15 | 0.105 (2) | 0.077 (2) | 0.075 (1) | −0.025 (1) | 0.034 (1) | −0.025 (1) |
C16 | 0.148 (3) | 0.091 (2) | 0.130 (3) | −0.050 (2) | 0.078 (2) | −0.060 (2) |
C17 | 0.117 (2) | 0.054 (2) | 0.197 (4) | −0.014 (1) | 0.106 (3) | −0.020 (2) |
C18 | 0.074 (2) | 0.062 (2) | 0.145 (2) | 0.005 (1) | 0.054 (2) | 0.018 (2) |
C19 | 0.057 (1) | 0.057 (1) | 0.086 (1) | −0.0014 (9) | 0.024 (1) | 0.003 (1) |
Geometric parameters (Å, º) top
O1—C3 | 1.224 (2) | C16—C17 | 1.357 (4) |
O2—C3 | 1.344 (2) | C17—C18 | 1.348 (4) |
O2—C11 | 1.455 (2) | C18—C19 | 1.367 (3) |
N1—C1 | 1.335 (2) | N1—H20 | 0.9 |
N1—C13 | 1.454 (2) | C4—H2 | 0.95 |
N2—N3 | 1.365 (2) | C6—H4 | 0.932 |
N2—C2 | 1.431 (2) | C8—H6 | 0.96 |
N2—C10 | 1.359 (2) | C11—H8 | 1.03 |
N3—N4 | 1.300 (2) | C12—H10 | 0.98 |
N4—C5 | 1.380 (3) | C12—H12 | 1.1 |
C1—C2 | 1.377 (2) | C13—H14 | 1.03 |
C1—C4 | 1.502 (3) | C16—H16 | 0.98 |
C2—C3 | 1.437 (2) | C18—H18 | 0.98 |
C5—C6 | 1.398 (3) | C4—H1 | 0.95 |
C5—C10 | 1.383 (2) | C4—H3 | 0.95 |
C6—C7 | 1.349 (3) | C7—H5 | 0.96 |
C7—C8 | 1.401 (3) | C9—H7 | 0.92 |
C8—C9 | 1.374 (3) | C11—H9 | 1.01 |
C9—C10 | 1.380 (3) | C12—H11 | 0.97 |
C11—C12 | 1.494 (3) | C13—H13 | 0.98 |
C13—C14 | 1.511 (3) | C15—H15 | 0.99 |
C14—C15 | 1.377 (3) | C17—H17 | 0.94 |
C14—C19 | 1.379 (3) | C19—H19 | 0.98 |
C15—C16 | 1.396 (4) | | |
| | | |
C3—O2—C11 | 115.2 (1) | C5—C6—H4 | 119.7 |
C1—N1—C13 | 126.0 (2) | C6—C7—H5 | 120.6 |
N3—N2—C2 | 121.4 (1) | C7—C8—H6 | 116.0 |
N3—N2—C10 | 109.6 (1) | C8—C9—H7 | 120.9 |
C2—N2—C10 | 129.0 (1) | O2—C11—H8 | 110.4 |
N2—N3—N4 | 109.0 (2) | C12—C11—H8 | 113.6 |
N3—N4—C5 | 108.1 (2) | H8—C11—H9 | 103.5 |
N1—C1—C4 | 117.4 (2) | C11—C12—H11 | 109.6 |
C2—C1—C4 | 121.1 (2) | H10—C12—H11 | 107.8 |
N2—C2—C1 | 118.4 (1) | H11—C12—H12 | 107.5 |
N2—C2—C3 | 118.2 (2) | N1—C13—H14 | 111.5 |
C1—C2—C3 | 123.5 (1) | C14—C13—H14 | 110.1 |
O1—C3—O2 | 122.0 (2) | C14—C15—H15 | 118.5 |
O1—C3—C2 | 123.9 (2) | C15—C16—H16 | 117.9 |
O2—C3—C2 | 114.0 (1) | C16—C17—H17 | 118.4 |
N4—C5—C6 | 130.4 (2) | C17—C18—H18 | 120.1 |
N4—C5—C10 | 108.6 (2) | C14—C19—H19 | 116.4 |
C6—C5—C10 | 121.1 (2) | C13—N1—H20 | 117.0 |
C5—C6—C7 | 116.7 (2) | C1—C4—H2 | 109.4 |
C6—C7—C8 | 122.1 (2) | H1—C4—H2 | 109.2 |
C7—C8—C9 | 121.7 (2) | H2—C4—H3 | 109.9 |
C8—C9—C10 | 116.0 (2) | C7—C6—H4 | 123.6 |
N2—C10—C5 | 104.8 (2) | C8—C7—H5 | 117.1 |
N2—C10—C9 | 132.9 (2) | C9—C8—H6 | 122.2 |
C5—C10—C9 | 122.3 (2) | C10—C9—H7 | 123.0 |
O2—C11—C12 | 108.1 (1) | O2—C11—H9 | 108.2 |
N1—C13—C14 | 114.5 (1) | C12—C11—H9 | 112.8 |
C13—C14—C15 | 122.9 (2) | C11—C12—H10 | 113.8 |
C13—C14—C19 | 118.7 (2) | C11—C12—H12 | 118.2 |
C15—C14—C19 | 118.3 (2) | H10—C12—H12 | 99.1 |
C14—C15—C16 | 119.3 (3) | N1—C13—H13 | 107.3 |
C15—C16—C17 | 120.6 (3) | C14—C13—H13 | 108.4 |
C16—C17—C18 | 120.3 (2) | H13—C13—H14 | 104.5 |
C17—C18—C19 | 120.0 (3) | C16—C15—H15 | 122.1 |
C14—C19—C18 | 121.5 (2) | C17—C16—H16 | 121.5 |
C1—N1—H20 | 116.8 | C18—C17—H17 | 121.3 |
C1—C4—H1 | 109.3 | C19—C18—H18 | 120.0 |
C1—C4—H3 | 109.5 | C18—C19—H19 | 122.1 |
C1—C4—H3 | 109.5 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H20···O1 | 0.91 | 1.96 | 2.675 (2) | 134 |
C4—H3···N2 | 0.95 | 2.36 | 2.834 (2) | 110 |
C4—H3···N3 | 0.95 | 2.68 | 3.275 (3) | 121 |
C15—H15···N1 | 0.99 | 2.53 | 2.884 (3) | 101 |
N1—H20···O1i | 0.91 | 2.55 | 3.218 (2) | 131 |
C19—H19···C1gii | 0.98 | 2.55 | 3.482 (2) | 159 |
C17—H17···N1iii | 0.94 | 2.69 | 3.582 (3) | 159 |
Symmetry codes: (i) −x+1, y, −z+3/2; (ii) x, −y, z+1/2; (iii) x, y−1, z. |
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