(E)-4-(4-Ethyl­phenyl­diazen­yl)-2,6-dimethylphenyl acrylate

The title compound, C₁₉H₂₀N₂O₂, has a trans configuration with respect to the diazene double bond. The dihedral angle between the planes of the two aromatic rings is 2.92 (3)°.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.009 Å
• Disorder in main residue
• R factor = 0.076
• wR factor = 0.230
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         34 Perc.
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for       C23A

Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.134
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.13
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
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       N22B
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C23B
PLAT301_ALERT_3_C Main Residue  Disorder .........................      15.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C16    -   C17    ...       1.38 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C10    -   C11    ...       1.37 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C10    -   C15    ...       1.37 Ang.
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C7

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C19 H20 N2 O2
            Atom count from the _atom_site data:  C18.93600 H19.87200 N2 O2
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G ALERT: check formula stoichiometry or atom site occupancies.
           From the CIF: _cell_formula_units_Z    2
           From the CIF: _chemical_formula_sum  C19 H20 N2 O2
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         38.00     37.87    0.13
           H         40.00     39.74    0.26
           N          4.00      4.00    0.00
           O          4.00      4.00    0.00

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  13 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I)

Crystal data

C19H20N2O2	Z = 2
Mr = 307.47	F(000) = 327.0
Triclinic, P1	Dx = 1.125 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4461 (15) Å	Cell parameters from 1578 reflections
b = 8.5053 (17) Å	θ = 1.9–25.1°
c = 14.260 (3) Å	µ = 0.07 mm^−1
α = 91.860 (16)°	T = 297 K
β = 103.587 (14)°	Prism, orange
γ = 113.006 (14)°	0.40 × 0.30 × 0.20 mm
V = 907.7 (3) Å^3

Data collection

STOE IPDS-2 diffractometer	3580 independent reflections
Radiation source: fine-focus sealed tube	1209 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.135
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 2.6°
ω scans	h = −10→10
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −10→10
Tmin = 0.975, Tmax = 0.987	l = −17→17
13759 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.076	H-atom parameters constrained
wR(F^2) = 0.231	w = 1/[σ^2(Fo^2) + (0.0671P)^2 + 0.1045P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
3580 reflections	Δρmax = 0.15 e Å^−3
250 parameters	Δρmin = −0.12 e Å^−3
82 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.018 (4)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.6512 (7)	0.8317 (7)	0.2584 (5)	0.1237 (15)
C2	0.7274 (6)	0.9547 (6)	0.3397 (4)	0.1136 (13)
H2	0.6580	0.9600	0.3806	0.136*
C3	0.9048 (6)	1.0710 (5)	0.3621 (3)	0.1015 (11)
C4	1.0022 (6)	1.0545 (6)	0.2979 (4)	0.1058 (12)
C5	0.9309 (8)	0.9334 (7)	0.2153 (4)	0.1184 (13)
C6	0.7520 (9)	0.8204 (6)	0.1963 (4)	0.1333 (16)
H6	0.6995	0.7368	0.1417	0.160*
C7	0.9910 (6)	1.2086 (5)	0.4502 (3)	0.1281 (14)
H7A	1.0891	1.1923	0.4918	0.192*
H7B	0.9046	1.2004	0.4853	0.192*
H7C	1.0338	1.3203	0.4294	0.192*
C8	1.0456 (7)	0.9271 (7)	0.1472 (4)	0.1594 (19)
H8A	1.0827	1.0328	0.1196	0.239*
H8B	0.9768	0.8320	0.0959	0.239*
H8C	1.1489	0.9126	0.1835	0.239*
C9	1.3093 (7)	1.1433 (8)	0.3781 (4)	0.1166 (14)
C10	0.1925 (8)	0.5574 (9)	0.2024 (6)	0.137 (2)
C11	0.1125 (11)	0.4362 (11)	0.1214 (7)	0.163 (2)
H11	0.1801	0.4250	0.0808	0.196*
C12	−0.0697 (10)	0.3286 (8)	0.0987 (4)	0.1591 (19)
H12	−0.1215	0.2478	0.0428	0.191*
C13	−0.1732 (7)	0.3400 (7)	0.1572 (5)	0.1298 (16)
C14	−0.0903 (8)	0.4627 (8)	0.2378 (5)	0.1345 (16)
H14	−0.1576	0.4744	0.2785	0.161*
C15	0.0888 (9)	0.5695 (7)	0.2610 (4)	0.1359 (16)
H15	0.1400	0.6506	0.3168	0.163*
C16	−0.3727 (7)	0.2164 (8)	0.1351 (5)	0.177 (2)
H16A	−0.3907	0.1066	0.1023	0.212*
H16B	−0.4045	0.1962	0.1960	0.212*
C17	−0.4847 (8)	0.2792 (9)	0.0776 (5)	0.208 (3)
H17A	−0.4773	0.3813	0.1125	0.312*
H17B	−0.6053	0.1934	0.0615	0.312*
H17C	−0.4492	0.3064	0.0189	0.312*
O1	1.1802 (5)	1.1783 (4)	0.3170 (2)	0.1239 (10)
O2	1.2794 (4)	1.0072 (5)	0.4081 (2)	0.1273 (11)
N22A	0.457 (2)	0.740 (3)	0.264 (2)	0.105 (6)	0.52 (3)
N23A	0.372 (2)	0.632 (2)	0.1908 (15)	0.110 (5)	0.52 (3)
N22B	0.380 (2)	0.701 (3)	0.257 (2)	0.092 (5)	0.48 (3)
N23B	0.479 (3)	0.6939 (18)	0.2042 (12)	0.098 (4)	0.48 (3)
C22A	1.507 (4)	1.261 (3)	0.4242 (19)	0.138 (7)	0.468 (8)
H22A	1.5867	1.2320	0.4693	0.166*	0.468 (8)
C23A	1.544 (3)	1.4025 (19)	0.3911 (16)	0.176 (7)	0.468 (8)
H23A	1.4555	1.4210	0.3460	0.211*	0.468 (8)
H23B	1.6588	1.4888	0.4118	0.211*	0.468 (8)
C22B	1.476 (2)	1.307 (2)	0.3934 (13)	0.104 (4)	0.532 (8)
H22B	1.4794	1.3936	0.3545	0.125*	0.532 (8)
C23B	1.6158 (17)	1.325 (2)	0.4630 (10)	0.128 (5)	0.468 (8)
H23D	1.6105	1.2372	0.5014	0.154*	0.468 (8)
H23C	1.7206	1.4241	0.4743	0.154*	0.468 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.098 (4)	0.105 (4)	0.143 (5)	0.034 (3)	−0.001 (4)	0.037 (4)
C2	0.096 (4)	0.114 (3)	0.130 (4)	0.046 (3)	0.020 (3)	0.038 (3)
C3	0.095 (3)	0.094 (3)	0.113 (3)	0.040 (3)	0.020 (3)	0.029 (2)
C4	0.097 (3)	0.097 (3)	0.121 (4)	0.037 (3)	0.028 (3)	0.037 (3)
C5	0.144 (4)	0.106 (3)	0.110 (4)	0.059 (3)	0.027 (3)	0.032 (3)
C6	0.147 (5)	0.101 (4)	0.122 (4)	0.045 (4)	−0.006 (4)	0.021 (3)
C7	0.119 (3)	0.121 (3)	0.135 (4)	0.043 (3)	0.029 (3)	0.013 (3)
C8	0.208 (6)	0.164 (5)	0.132 (4)	0.090 (4)	0.066 (4)	0.035 (3)
C9	0.101 (4)	0.123 (4)	0.120 (4)	0.037 (4)	0.038 (3)	−0.001 (3)
C10	0.094 (4)	0.139 (5)	0.189 (6)	0.058 (4)	0.035 (5)	0.083 (5)
C11	0.141 (6)	0.173 (6)	0.222 (7)	0.094 (5)	0.076 (5)	0.063 (5)
C12	0.144 (5)	0.155 (5)	0.183 (6)	0.069 (5)	0.040 (5)	0.013 (4)
C13	0.094 (4)	0.125 (4)	0.160 (5)	0.045 (3)	0.015 (4)	0.032 (4)
C14	0.102 (4)	0.145 (4)	0.148 (5)	0.041 (3)	0.030 (3)	0.040 (4)
C15	0.114 (4)	0.137 (4)	0.133 (4)	0.037 (4)	0.012 (3)	0.042 (3)
C16	0.125 (5)	0.163 (5)	0.225 (6)	0.059 (4)	0.011 (4)	0.056 (4)
C17	0.139 (5)	0.211 (6)	0.248 (7)	0.064 (5)	0.014 (4)	0.058 (6)
O1	0.111 (2)	0.114 (2)	0.144 (3)	0.038 (2)	0.0424 (19)	0.0379 (18)
O2	0.105 (2)	0.141 (3)	0.132 (2)	0.054 (2)	0.0189 (17)	0.025 (2)
N22A	0.106 (12)	0.100 (10)	0.095 (9)	0.042 (9)	0.001 (11)	0.011 (8)
N23A	0.108 (10)	0.105 (8)	0.110 (9)	0.047 (7)	0.012 (8)	0.011 (7)
N22B	0.087 (10)	0.093 (10)	0.086 (10)	0.033 (8)	0.012 (9)	0.005 (8)
N23B	0.107 (10)	0.103 (8)	0.084 (7)	0.051 (8)	0.016 (8)	0.005 (6)
C23A	0.169 (14)	0.142 (13)	0.194 (14)	0.022 (12)	0.078 (12)	0.033 (12)
C22B	0.093 (7)	0.091 (10)	0.136 (11)	0.032 (7)	0.049 (6)	0.043 (7)
C22A	0.161 (17)	0.114 (13)	0.132 (17)	0.043 (12)	0.051 (13)	−0.003 (10)
C23B	0.100 (9)	0.102 (9)	0.149 (11)	0.022 (7)	0.008 (7)	−0.004 (8)

Geometric parameters (Å, º)

C1—C2	1.377 (6)	C10—N22B	1.568 (17)
C1—C6	1.390 (7)	C11—C12	1.398 (8)
C1—N23B	1.470 (17)	C11—H11	0.93
C1—N22A	1.541 (17)	C12—C13	1.369 (7)
C2—C3	1.386 (5)	C12—H12	0.93
C2—H2	0.93	C13—C14	1.368 (7)
C3—C4	1.404 (5)	C13—C16	1.545 (6)
C3—C7	1.512 (5)	C14—C15	1.377 (6)
C4—C5	1.383 (6)	C14—H14	0.93
C4—O1	1.413 (5)	C15—H15	0.93
C5—C6	1.392 (6)	C16—C17	1.382 (6)
C5—C8	1.538 (6)	C16—H16A	0.97
C6—H6	0.93	C16—H16B	0.97
C7—H7A	0.96	C17—H17A	0.96
C7—H7B	0.96	C17—H17B	0.96
C7—H7C	0.96	C17—H17C	0.96
C8—H8A	0.96	N22A—N23A	1.23 (5)
C8—H8B	0.96	N22B—N23B	1.27 (5)
C8—H8C	0.96	C23A—C22A	1.26 (2)
C9—O2	1.201 (5)	C23A—H23A	0.93
C9—O1	1.364 (6)	C23A—H23B	0.93
C9—C22B	1.510 (18)	C22B—C23B	1.305 (19)
C9—C22A	1.53 (3)	C22B—H22B	0.93
C10—C11	1.365 (8)	C22A—H22A	0.93
C10—C15	1.373 (7)	C23B—H23D	0.93
C10—N23A	1.453 (16)	C23B—H23C	0.93
C2—C1—C6	120.4 (5)	C10—C11—H11	119.5
C2—C1—N23B	141.6 (11)	C12—C11—H11	119.5
C6—C1—N23B	98.0 (11)	C13—C12—C11	121.3 (6)
C2—C1—N22A	102.3 (14)	C13—C12—H12	119.4
C6—C1—N22A	137.3 (14)	C11—C12—H12	119.4
C1—C2—C3	121.8 (5)	C14—C13—C12	116.8 (5)
C1—C2—H2	119.1	C14—C13—C16	121.6 (6)
C3—C2—H2	119.1	C12—C13—C16	121.6 (7)
C2—C3—C4	116.1 (4)	C13—C14—C15	122.6 (5)
C2—C3—C7	122.8 (5)	C13—C14—H14	118.7
C4—C3—C7	121.1 (4)	C15—C14—H14	118.7
C5—C4—C3	124.1 (5)	C10—C15—C14	120.5 (6)
C5—C4—O1	119.2 (5)	C10—C15—H15	119.7
C3—C4—O1	116.5 (5)	C14—C15—H15	119.7
C4—C5—C6	117.3 (5)	C17—C16—C13	113.1 (5)
C4—C5—C8	120.8 (5)	C17—C16—H16A	109.0
C6—C5—C8	121.9 (6)	C13—C16—H16A	109.0
C1—C6—C5	120.4 (5)	C17—C16—H16B	109.0
C1—C6—H6	119.8	C13—C16—H16B	109.0
C5—C6—H6	119.8	H16A—C16—H16B	107.8
C3—C7—H7A	109.5	C16—C17—H17A	109.5
C3—C7—H7B	109.5	C16—C17—H17B	109.5
H7A—C7—H7B	109.5	H17A—C17—H17B	109.5
C3—C7—H7C	109.5	C16—C17—H17C	109.5
H7A—C7—H7C	109.5	H17A—C17—H17C	109.5
H7B—C7—H7C	109.5	H17B—C17—H17C	109.5
C5—C8—H8A	109.5	C9—O1—C4	117.3 (3)
C5—C8—H8B	109.5	N23A—N22A—C1	108 (2)
H8A—C8—H8B	109.5	N22A—N23A—C10	103 (2)
C5—C8—H8C	109.5	N23B—N22B—C10	104 (2)
H8A—C8—H8C	109.5	N22B—N23B—C1	100.8 (18)
H8B—C8—H8C	109.5	C22A—C23A—H23A	120.0
O2—C9—O1	122.7 (5)	C22A—C23A—H23B	120.0
O2—C9—C22B	133.3 (7)	H23A—C23A—H23B	120.0
O1—C9—C22B	104.0 (7)	C23B—C22B—C9	118.0 (14)
O2—C9—C22A	107.8 (10)	C23B—C22B—H22B	121.0
O1—C9—C22A	129.5 (10)	C9—C22B—H22B	121.0
C11—C10—C15	118.0 (6)	C23A—C22A—C9	109 (3)
C11—C10—N23A	98.9 (11)	C23A—C22A—H22A	125.4
C15—C10—N23A	143.1 (11)	C9—C22A—H22A	125.4
C11—C10—N22B	140.1 (15)	C22B—C23B—H23D	120.0
C15—C10—N22B	101.9 (14)	C22B—C23B—H23C	120.0
C10—C11—C12	120.9 (7)	H23D—C23B—H23C	120.0
C6—C1—C2—C3	0.3 (6)	C13—C14—C15—C10	0.5 (7)
N23B—C1—C2—C3	−176.5 (8)	C14—C13—C16—C17	90.8 (7)
N22A—C1—C2—C3	−178.9 (9)	C12—C13—C16—C17	−91.2 (7)
C1—C2—C3—C4	−0.7 (5)	O2—C9—O1—C4	6.9 (6)
C1—C2—C3—C7	179.2 (4)	C22B—C9—O1—C4	−172.8 (9)
C2—C3—C4—C5	1.0 (5)	C22A—C9—O1—C4	−170.1 (13)
C7—C3—C4—C5	−178.9 (4)	C5—C4—O1—C9	−95.5 (4)
C2—C3—C4—O1	176.6 (3)	C3—C4—O1—C9	88.7 (4)
C7—C3—C4—O1	−3.4 (5)	C2—C1—N22A—N23A	175.8 (13)
C3—C4—C5—C6	−0.9 (6)	C6—C1—N22A—N23A	−3 (2)
O1—C4—C5—C6	−176.3 (3)	N23B—C1—N22A—N23A	−1.8 (12)
C3—C4—C5—C8	178.3 (4)	C1—N22A—N23A—C10	−178.5 (10)
O1—C4—C5—C8	2.9 (5)	C11—C10—N23A—N22A	−177.1 (12)
C2—C1—C6—C5	−0.1 (6)	C15—C10—N23A—N22A	4.1 (17)
N23B—C1—C6—C5	177.8 (6)	N22B—C10—N23A—N22A	2 (2)
N22A—C1—C6—C5	178.7 (12)	C11—C10—N22B—N23B	1 (2)
C4—C5—C6—C1	0.4 (6)	C15—C10—N22B—N23B	−179.5 (12)
C8—C5—C6—C1	−178.8 (4)	N23A—C10—N22B—N23B	−0.9 (12)
C15—C10—C11—C12	0.4 (8)	C10—N22B—N23B—C1	179.3 (11)
N23A—C10—C11—C12	−178.8 (6)	C2—C1—N23B—N22B	−1.5 (16)
N22B—C10—C11—C12	180.0 (14)	C6—C1—N23B—N22B	−178.7 (12)
C10—C11—C12—C13	−0.7 (8)	N22A—C1—N23B—N22B	2 (2)
C11—C12—C13—C14	0.8 (8)	O2—C9—C22B—C23B	−12 (2)
C11—C12—C13—C16	−177.3 (5)	O1—C9—C22B—C23B	167.5 (14)
C12—C13—C14—C15	−0.8 (7)	C22A—C9—C22B—C23B	−8 (3)
C16—C13—C14—C15	177.4 (4)	O2—C9—C22A—C23A	177.6 (17)
C11—C10—C15—C14	−0.3 (7)	O1—C9—C22A—C23A	−5 (3)
N23A—C10—C15—C14	178.4 (8)	C22B—C9—C22A—C23A	1 (2)
N22B—C10—C15—C14	180.0 (9)