Ethyl (E)-2-(1H-benzotriazol-1-yl)-3-(N-benzyl­amino)­but-2-enoate

The title compound, C₁₉H₂₀N₄O₂, 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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](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            been superseded by _refine_ls_goodness_of_fit_ref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            superseded by _refine_ls_R_factor_gt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            superseded by _refine_ls_wR_factor_ref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            superseded by _refine_ls_shift/su_max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

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Computing details

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.

Crystal data

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) Å^3	Prismatic, colorless
Z = 4	0.30 × 0.30 × 0.20 mm

Data collection

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

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[F^2 > 2σ(F^2)] = 0.042	(Δ/σ)max = 0.001
wR(F^2) = 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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O1^i	0.91	2.55	3.218 (2)	131
C19—H19···C1g^ii	0.98	2.55	3.482 (2)	159
C17—H17···N1^iii	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.