(E)-3-(2-Ethoxy­quinolin-3-yl)-1-(2-hydr­oxy-6-methyl­phen­yl)prop-2-en-1-one

The title mol­ecule, C₂₁H₁₉NO₃, consists of a 2-ethoxy­quinolyl group linked to an aroylvinyl group. The quinolyl ring forms a dihedral angle of 2.88 (6)° with the benzene ring. The crystal structure can be described by two types of crossed layers which are parallel to (110) and (10). The packing is stabilized by C—H...O and O—H...O intra- and inter­molecular hydrogen bonds, resulting in the formation of a two-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.033
• wR factor = 0.085
• Data-to-parameter ratio = 7.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.92
PLAT128_ALERT_4_C Non-standard setting of Space group Pna21   ....    Pn21a

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.32
           From the CIF: _reflns_number_total               1869
           Count of symmetry unique reflns         1872
           Completeness (_total/calc)             99.84%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

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

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

---

Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia,1997)and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

(E)-3-(2-Ethoxyquinolin-3-yl)-1-(2-hydroxy-6-methylphenyl)prop-2-en-1-one

Crystal data

C21H19NO3	F(000) = 704
Mr = 333.37	Dx = 1.259 Mg m^−3
Orthorhombic, Pn21a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2ac -2n	Cell parameters from 24253 reflections
a = 7.6026 (2) Å	θ = 2.8–26.3°
b = 14.7425 (4) Å	µ = 0.08 mm^−1
c = 15.6862 (4) Å	T = 296 K
V = 1758.13 (8) Å^3	Needle, yellow
Z = 4	0.15 × 0.11 × 0.06 mm

Data collection

Bruker–Nonius KappaCCD diffractometer	1348 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.055
Graphite monochromator	θmax = 26.3°, θmin = 2.8°
φ scans, and ω scans with κ offsets	h = −9→9
24253 measured reflections	k = −18→18
1869 independent reflections	l = −19→18

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)] = 0.033	H-atom parameters constrained
wR(F^2) = 0.085	w = 1/[σ^2(Fo^2) + (0.0293P)^2 + 1.3984P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.006
1869 reflections	Δρmax = 0.10 e Å^−3
236 parameters	Δρmin = −0.12 e Å^−3
1 restraint	Extinction correction: SHELXL97
Primary atom site location: structure-invariant direct methods	Extinction coefficient: none

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O1	0.0711 (2)	0.63718 (11)	0.14351 (8)	0.0521 (5)
O2	−0.0528 (3)	0.50410 (13)	0.44150 (10)	0.0728 (7)
O3	−0.1870 (3)	0.35064 (14)	0.47616 (11)	0.0856 (8)
N1	0.1983 (3)	0.77749 (13)	0.13619 (11)	0.0489 (6)
C1	0.1395 (3)	0.71106 (16)	0.18284 (12)	0.0434 (7)
C2	0.1382 (3)	0.70910 (16)	0.27460 (11)	0.0422 (6)
C3	0.2078 (3)	0.78397 (16)	0.31388 (13)	0.0468 (7)
C4	0.2741 (3)	0.85789 (15)	0.26708 (14)	0.0473 (7)
C5	0.3456 (3)	0.93651 (17)	0.30510 (17)	0.0591 (9)
C6	0.4052 (3)	1.00590 (18)	0.2555 (2)	0.0677 (10)
C7	0.3977 (3)	1.00029 (18)	0.16672 (19)	0.0682 (10)
C8	0.3303 (3)	0.92516 (17)	0.12784 (18)	0.0597 (9)
C9	0.2666 (3)	0.85209 (16)	0.17705 (14)	0.0479 (7)
C10	0.0683 (3)	0.63482 (17)	0.32600 (13)	0.0468 (7)
C11	−0.0018 (3)	0.55650 (15)	0.30215 (14)	0.0503 (8)
C12	−0.0656 (3)	0.48933 (16)	0.36335 (14)	0.0520 (8)
C13	−0.1439 (3)	0.40414 (16)	0.33213 (14)	0.0496 (8)
C14	−0.1602 (3)	0.38344 (16)	0.24530 (15)	0.0528 (8)
C15	−0.2252 (3)	0.30192 (18)	0.21596 (17)	0.0631 (10)
C16	−0.2742 (4)	0.2383 (2)	0.2758 (2)	0.0773 (13)
C17	−0.2609 (4)	0.2549 (2)	0.3612 (2)	0.0800 (11)
C18	−0.1983 (3)	0.33734 (19)	0.39124 (17)	0.0619 (9)
C19	−0.2380 (4)	0.2816 (3)	0.1222 (2)	0.0893 (12)
C20	0.0641 (3)	0.6380 (2)	0.05150 (12)	0.0612 (9)
C21	−0.0297 (4)	0.5533 (2)	0.02490 (15)	0.0750 (11)
H3	0.21117	0.78601	0.37311	0.0561*
H5	0.35195	0.94095	0.36416	0.0709*
H6	0.45141	1.05758	0.28111	0.0812*
H7	0.43898	1.04822	0.13378	0.0817*
H8	0.32637	0.92210	0.06865	0.0717*
H10	0.07380	0.64387	0.38461	0.0561*
H11	−0.01084	0.54379	0.24424	0.0603*
H13A	0.18200	0.63905	0.02788	0.0734*
H13B	0.00118	0.69108	0.03149	0.0734*
H14	−0.12556	0.42674	0.20559	0.0634*
H16	−0.31741	0.18252	0.25748	0.0926*
H17	−0.29436	0.21031	0.39984	0.0960*
H19A	−0.23530	0.33734	0.09054	0.1344*
H19B	−0.34623	0.25031	0.11074	0.1344*
H19C	−0.14067	0.24418	0.10533	0.1344*
H21A	−0.03752	0.55129	−0.03616	0.1123*
H21B	−0.14595	0.55302	0.04883	0.1123*
H21C	0.03406	0.50132	0.04495	0.1123*
H33	−0.14849	0.40163	0.48555	0.1284*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0711 (9)	0.0490 (9)	0.0361 (7)	−0.0058 (8)	−0.0016 (7)	−0.0024 (7)
O2	0.1039 (14)	0.0721 (12)	0.0424 (9)	−0.0109 (10)	−0.0007 (9)	0.0080 (8)
O3	0.1050 (14)	0.0858 (14)	0.0661 (12)	−0.0122 (12)	0.0142 (10)	0.0260 (11)
N1	0.0548 (10)	0.0481 (11)	0.0439 (9)	0.0050 (9)	0.0009 (9)	0.0049 (9)
C1	0.0460 (12)	0.0428 (12)	0.0414 (10)	0.0062 (10)	−0.0016 (9)	−0.0015 (11)
C2	0.0451 (12)	0.0407 (11)	0.0407 (10)	0.0083 (9)	0.0001 (9)	0.0007 (10)
C3	0.0502 (12)	0.0484 (13)	0.0417 (11)	0.0092 (10)	−0.0033 (10)	−0.0034 (10)
C4	0.0426 (12)	0.0420 (13)	0.0574 (13)	0.0057 (10)	−0.0003 (10)	−0.0032 (11)
C5	0.0517 (14)	0.0528 (16)	0.0728 (16)	0.0015 (12)	−0.0072 (12)	−0.0078 (12)
C6	0.0546 (14)	0.0484 (15)	0.100 (2)	−0.0031 (12)	−0.0056 (14)	−0.0041 (14)
C7	0.0561 (15)	0.0515 (16)	0.097 (2)	−0.0004 (13)	0.0033 (13)	0.0178 (15)
C8	0.0582 (14)	0.0515 (16)	0.0695 (15)	0.0071 (12)	0.0038 (12)	0.0127 (12)
C9	0.0444 (12)	0.0437 (13)	0.0555 (12)	0.0093 (10)	−0.0017 (10)	0.0066 (11)
C10	0.0519 (12)	0.0502 (14)	0.0383 (10)	0.0068 (12)	0.0005 (9)	0.0028 (10)
C11	0.0639 (14)	0.0461 (14)	0.0408 (11)	−0.0024 (12)	0.0016 (10)	0.0027 (10)
C12	0.0581 (14)	0.0523 (15)	0.0455 (12)	0.0067 (12)	0.0022 (10)	0.0081 (10)
C13	0.0481 (13)	0.0457 (13)	0.0551 (14)	0.0055 (11)	0.0070 (10)	0.0085 (10)
C14	0.0510 (12)	0.0497 (15)	0.0577 (14)	0.0017 (12)	0.0068 (10)	0.0017 (11)
C15	0.0459 (14)	0.0591 (18)	0.0842 (19)	0.0015 (12)	0.0056 (12)	−0.0146 (15)
C16	0.0586 (17)	0.0544 (17)	0.119 (3)	−0.0049 (13)	0.0114 (16)	−0.0084 (18)
C17	0.0700 (19)	0.0600 (19)	0.110 (2)	−0.0077 (14)	0.0194 (16)	0.0198 (19)
C18	0.0592 (15)	0.0585 (17)	0.0679 (16)	0.0033 (13)	0.0104 (13)	0.0178 (13)
C19	0.075 (2)	0.098 (2)	0.095 (2)	−0.0014 (18)	0.0004 (15)	−0.0370 (19)
C20	0.0790 (17)	0.0703 (17)	0.0343 (11)	0.0017 (14)	−0.0012 (10)	−0.0031 (12)
C21	0.095 (2)	0.078 (2)	0.0519 (16)	−0.0002 (18)	−0.0067 (12)	−0.0168 (14)

Geometric parameters (Å, º)

O1—C1	1.356 (3)	C15—C16	1.378 (4)
O1—C20	1.444 (2)	C15—C19	1.504 (4)
O2—C12	1.249 (3)	C16—C17	1.366 (4)
O3—C18	1.349 (3)	C17—C18	1.388 (4)
O3—H33	0.8200	C20—C21	1.497 (4)
N1—C1	1.302 (3)	C3—H3	0.9300
N1—C9	1.375 (3)	C5—H5	0.9300
C1—C2	1.440 (3)	C6—H6	0.9300
C2—C3	1.370 (3)	C7—H7	0.9300
C2—C10	1.460 (3)	C8—H8	0.9300
C3—C4	1.407 (3)	C10—H10	0.9300
C4—C5	1.412 (3)	C11—H11	0.9300
C4—C9	1.416 (3)	C14—H14	0.9300
C5—C6	1.363 (4)	C16—H16	0.9300
C6—C7	1.396 (4)	C17—H17	0.9300
C7—C8	1.364 (4)	C19—H19A	0.9600
C8—C9	1.411 (3)	C19—H19B	0.9600
C10—C11	1.326 (3)	C19—H19C	0.9600
C11—C12	1.462 (3)	C20—H13A	0.9700
C12—C13	1.474 (3)	C20—H13B	0.9700
C13—C14	1.401 (3)	C21—H21A	0.9600
C13—C18	1.414 (4)	C21—H21B	0.9600
C14—C15	1.379 (4)	C21—H21C	0.9600
O1···C11	2.813 (3)	C12···H33	2.4000
O2···O3	2.541 (3)	C14···H11	2.6200
O3···O2	2.541 (3)	C17···H19C^ii	2.9400
O1···H11	2.1900	C18···H19B^iv	2.9700
O2···H10	2.4400	C20···H19C^v	2.9700
O2···H8^i	2.9000	H3···H5	2.5300
O2···H13A^ii	2.8700	H3···H10	2.3500
O2···H33	1.8100	H3···O3^vi	2.5600
O3···H3^iii	2.5600	H5···H3	2.5300
N1···H13A	2.6600	H6···H16^vii	2.5700
N1···H13B	2.5600	H8···O2^viii	2.9000
C1···C11^iv	3.562 (3)	H10···O2	2.4400
C1···C3^ii	3.454 (3)	H10···H3	2.3500
C1···C10^iv	3.451 (3)	H11···O1	2.1900
C2···C4^ii	3.592 (3)	H11···C1	2.8800
C3···C9^ii	3.504 (3)	H11···C14	2.6200
C3···C1^iv	3.454 (3)	H11···H14	2.0300
C4···C2^iv	3.592 (3)	H13A···N1	2.6600
C4···C6^ii	3.571 (3)	H13A···O2^iv	2.8700
C5···C9^iv	3.446 (3)	H13B···N1	2.5600
C5···C7^ii	3.560 (3)	H13B···H19C^v	2.5200
C6···C4^iv	3.571 (3)	H14···C11	2.6200
C7···C5^iv	3.560 (3)	H14···H11	2.0300
C9···C5^ii	3.446 (3)	H14···H19A	2.3900
C9···C3^iv	3.504 (3)	H16···H6^ix	2.5700
C10···C1^ii	3.451 (3)	H16···H19B	2.5200
C11···C1^ii	3.562 (3)	H19A···H14	2.3900
C11···O1	2.813 (3)	H19B···H16	2.5200
C14···C15^iv	3.571 (3)	H19B···C18^ii	2.9700
C15···C16^iv	3.557 (4)	H19C···C20^x	2.9700
C15···C14^ii	3.571 (3)	H19C···H13B^x	2.5200
C16···C15^ii	3.557 (4)	H19C···C17^iv	2.9400
C1···H11	2.8800	H33···O2	1.8100
C11···H14	2.6200	H33···C12	2.4000
C1—O1—C20	117.53 (18)	C2—C3—H3	119.00
C18—O3—H33	109.00	C4—C3—H3	119.00
C1—N1—C9	118.00 (18)	C4—C5—H5	120.00
O1—C1—N1	118.71 (17)	C6—C5—H5	120.00
N1—C1—C2	125.4 (2)	C5—C6—H6	120.00
O1—C1—C2	115.87 (19)	C7—C6—H6	120.00
C1—C2—C3	115.5 (2)	C6—C7—H7	120.00
C3—C2—C10	119.76 (17)	C8—C7—H7	120.00
C1—C2—C10	124.7 (2)	C7—C8—H8	120.00
C2—C3—C4	121.83 (19)	C9—C8—H8	120.00
C3—C4—C9	117.3 (2)	C2—C10—H10	115.00
C5—C4—C9	119.1 (2)	C11—C10—H10	115.00
C3—C4—C5	123.6 (2)	C10—C11—H11	119.00
C4—C5—C6	120.2 (2)	C12—C11—H11	119.00
C5—C6—C7	120.8 (2)	C13—C14—H14	118.00
C6—C7—C8	120.6 (3)	C15—C14—H14	118.00
C7—C8—C9	120.3 (3)	C15—C16—H16	119.00
N1—C9—C8	119.0 (2)	C17—C16—H16	119.00
C4—C9—C8	119.1 (2)	C16—C17—H17	120.00
N1—C9—C4	121.9 (2)	C18—C17—H17	119.00
C2—C10—C11	130.1 (2)	C15—C19—H19A	110.00
C10—C11—C12	122.6 (2)	C15—C19—H19B	110.00
O2—C12—C11	120.0 (2)	C15—C19—H19C	110.00
C11—C12—C13	119.54 (19)	H19A—C19—H19B	109.00
O2—C12—C13	120.4 (2)	H19A—C19—H19C	109.00
C12—C13—C18	119.6 (2)	H19B—C19—H19C	109.00
C14—C13—C18	117.4 (2)	O1—C20—H13A	110.00
C12—C13—C14	123.0 (2)	O1—C20—H13B	110.00
C13—C14—C15	123.1 (2)	C21—C20—H13A	110.00
C14—C15—C16	117.6 (2)	C21—C20—H13B	110.00
C14—C15—C19	121.6 (3)	H13A—C20—H13B	109.00
C16—C15—C19	120.9 (3)	C20—C21—H21A	109.00
C15—C16—C17	121.8 (3)	C20—C21—H21B	109.00
C16—C17—C18	121.0 (3)	C20—C21—H21C	110.00
O3—C18—C13	121.8 (2)	H21A—C21—H21B	109.00
C13—C18—C17	119.2 (2)	H21A—C21—H21C	109.00
O3—C18—C17	119.0 (3)	H21B—C21—H21C	109.00
O1—C20—C21	106.80 (19)
C20—O1—C1—N1	−1.5 (3)	C5—C6—C7—C8	0.1 (4)
C20—O1—C1—C2	177.77 (19)	C6—C7—C8—C9	0.2 (4)
C1—O1—C20—C21	−175.3 (2)	C7—C8—C9—C4	−0.1 (3)
C9—N1—C1—O1	179.7 (2)	C7—C8—C9—N1	179.6 (2)
C9—N1—C1—C2	0.6 (4)	C2—C10—C11—C12	180.0 (2)
C1—N1—C9—C8	−179.7 (2)	C10—C11—C12—O2	−1.1 (4)
C1—N1—C9—C4	0.0 (4)	C10—C11—C12—C13	179.3 (2)
O1—C1—C2—C10	−0.5 (3)	O2—C12—C13—C14	−179.4 (2)
N1—C1—C2—C3	−0.9 (4)	O2—C12—C13—C18	−2.5 (3)
O1—C1—C2—C3	179.9 (2)	C11—C12—C13—C14	0.3 (3)
N1—C1—C2—C10	178.6 (2)	C11—C12—C13—C18	177.1 (2)
C10—C2—C3—C4	−178.9 (2)	C12—C13—C14—C15	176.6 (2)
C1—C2—C3—C4	0.6 (3)	C18—C13—C14—C15	−0.3 (3)
C3—C2—C10—C11	−178.9 (2)	C12—C13—C18—O3	2.6 (4)
C1—C2—C10—C11	1.6 (4)	C12—C13—C18—C17	−175.7 (2)
C2—C3—C4—C9	−0.1 (3)	C14—C13—C18—O3	179.7 (2)
C2—C3—C4—C5	179.5 (2)	C14—C13—C18—C17	1.3 (3)
C3—C4—C5—C6	−179.1 (2)	C13—C14—C15—C16	−0.6 (4)
C3—C4—C9—C8	179.4 (2)	C13—C14—C15—C19	−179.0 (2)
C9—C4—C5—C6	0.5 (3)	C14—C15—C16—C17	0.6 (4)
C3—C4—C9—N1	−0.3 (3)	C19—C15—C16—C17	178.9 (3)
C5—C4—C9—C8	−0.2 (3)	C15—C16—C17—C18	0.5 (5)
C5—C4—C9—N1	−179.9 (2)	C16—C17—C18—O3	−179.8 (3)
C4—C5—C6—C7	−0.4 (4)	C16—C17—C18—C13	−1.5 (4)

Symmetry codes: (i) −x+1/2, y−1/2, z+1/2; (ii) x−1/2, y, −z+1/2; (iii) −x, y−1/2, −z+1; (iv) x+1/2, y, −z+1/2; (v) −x, y+1/2, −z; (vi) −x, y+1/2, −z+1; (vii) x+1, y+1, z; (viii) −x+1/2, y+1/2, z−1/2; (ix) x−1, y−1, z; (x) −x, y−1/2, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H33···O2	0.8200	1.8100	2.541 (3)	147.00
C3—H3···O3^vi	0.9300	2.5600	3.441 (3)	159.00
C10—H10···O2	0.9300	2.4400	2.801 (3)	103.00
C11—H11···O1	0.9300	2.1900	2.813 (3)	124.00

Symmetry code: (vi) −x, y+1/2, −z+1.