Crystal structure and Hirshfeld surface analysis of (E)-6-(4-hy­droxy-3-meth­oxy­styr­yl)-4,5-di­hydro­pyridazin-3(2H)-one

In the title com­pound, inter­molecular C—H...O, O—H...O and N—H...O hydrogen bonds link the mol­ecules into a three-dimensional supra­molecular network.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.056
• wR factor = 0.147
• Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.7 Note
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .         33 Ang   3
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     14.065 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.665 Check

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size ....       0.72 mm
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   0 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
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXT2017 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012), SHELXL2018 (Sheldrick, 2015b), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

(E)-6-(4-Hydroxy-3-methoxystyryl)-4,5-dihydropyridazin-3(2H)-\ one

Crystal data

C13H14N2O3	Z = 2
Mr = 246.26	F(000) = 260
Triclinic, P1	Dx = 1.330 Mg m^−3
a = 6.0828 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.4246 (13) Å	Cell parameters from 13077 reflections
c = 11.1724 (16) Å	θ = 2.2–30.7°
α = 75.838 (11)°	µ = 0.10 mm^−1
β = 83.099 (12)°	T = 293 K
γ = 84.059 (11)°	Prism, yellow
V = 614.70 (16) Å^3	0.72 × 0.39 × 0.16 mm

Data collection

Stoe IPDS 2 diffractometer	1506 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm^-1	Rint = 0.054
rotation method scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −7→7
Tmin = 0.944, Tmax = 0.989	k = −11→11
6563 measured reflections	l = −13→13
2426 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.056	H-atom parameters constrained
wR(F^2) = 0.147	w = 1/[σ^2(Fo^2) + (0.0747P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
2426 reflections	Δρmax = 0.17 e Å^−3
165 parameters	Δρmin = −0.17 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.7518 (3)	0.88682 (19)	0.99156 (15)	0.0601 (5)
O3	0.4960 (3)	0.58008 (19)	0.11563 (16)	0.0614 (5)
O2	0.1290 (3)	0.7317 (2)	0.05778 (16)	0.0636 (5)
H2	0.016474	0.786724	0.044599	0.095*
N1	0.4947 (3)	0.9323 (2)	0.85757 (17)	0.0525 (5)
H1	0.429651	0.995567	0.896673	0.063*
N2	0.3918 (3)	0.9139 (2)	0.75870 (17)	0.0519 (5)
C9	0.3982 (4)	0.6576 (2)	0.1986 (2)	0.0497 (6)
C5	0.3927 (4)	0.8291 (3)	0.5807 (2)	0.0506 (6)
H5	0.252921	0.878478	0.572201	0.061*
C1	0.6829 (4)	0.8631 (3)	0.8987 (2)	0.0492 (6)
C4	0.5043 (4)	0.8412 (2)	0.6851 (2)	0.0472 (6)
C8	0.4803 (4)	0.6645 (3)	0.3066 (2)	0.0521 (6)
H8	0.616062	0.614251	0.326018	0.062*
C11	0.0780 (4)	0.8118 (3)	0.2494 (2)	0.0538 (6)
H11	−0.059111	0.860442	0.230853	0.065*
C7	0.3664 (4)	0.7445 (2)	0.3875 (2)	0.0496 (6)
C10	0.1954 (4)	0.7364 (2)	0.1681 (2)	0.0487 (6)
C6	0.4707 (4)	0.7544 (3)	0.4962 (2)	0.0549 (6)
H6	0.607897	0.702171	0.507391	0.066*
C12	0.1607 (4)	0.8164 (3)	0.3580 (2)	0.0552 (6)
H12	0.078822	0.867751	0.411814	0.066*
C13	0.7007 (4)	0.4965 (3)	0.1419 (3)	0.0614 (7)
H13A	0.745228	0.441469	0.079994	0.092*
H13B	0.682204	0.430200	0.222071	0.092*
H13C	0.812721	0.561367	0.141331	0.092*
C2	0.7972 (5)	0.7565 (3)	0.8299 (3)	0.0694 (8)
H2A	0.761992	0.658432	0.875007	0.083*
H2B	0.956271	0.761159	0.827335	0.083*
C3	0.7375 (4)	0.7807 (3)	0.7002 (2)	0.0673 (8)
H3A	0.836608	0.847839	0.645178	0.081*
H3B	0.760060	0.688125	0.675416	0.081*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0632 (11)	0.0804 (12)	0.0479 (10)	0.0136 (8)	−0.0292 (8)	−0.0331 (8)
O3	0.0642 (11)	0.0739 (11)	0.0579 (10)	0.0218 (8)	−0.0273 (9)	−0.0392 (9)
O2	0.0633 (12)	0.0859 (13)	0.0537 (10)	0.0146 (9)	−0.0326 (9)	−0.0349 (9)
N1	0.0536 (12)	0.0686 (13)	0.0448 (11)	0.0094 (9)	−0.0204 (9)	−0.0299 (10)
N2	0.0510 (12)	0.0670 (13)	0.0450 (11)	0.0068 (9)	−0.0213 (9)	−0.0237 (10)
C9	0.0569 (14)	0.0515 (13)	0.0479 (13)	0.0029 (11)	−0.0190 (11)	−0.0217 (11)
C5	0.0550 (14)	0.0602 (14)	0.0422 (12)	0.0029 (11)	−0.0196 (11)	−0.0185 (11)
C1	0.0539 (14)	0.0552 (14)	0.0427 (12)	0.0056 (11)	−0.0182 (11)	−0.0172 (11)
C4	0.0524 (14)	0.0522 (13)	0.0416 (12)	0.0007 (10)	−0.0152 (11)	−0.0168 (10)
C8	0.0533 (14)	0.0584 (14)	0.0511 (14)	0.0074 (11)	−0.0248 (12)	−0.0207 (11)
C11	0.0495 (13)	0.0675 (15)	0.0506 (14)	0.0090 (11)	−0.0211 (11)	−0.0237 (12)
C7	0.0579 (14)	0.0565 (14)	0.0412 (12)	0.0011 (11)	−0.0181 (11)	−0.0204 (11)
C10	0.0540 (14)	0.0560 (14)	0.0432 (13)	−0.0004 (11)	−0.0192 (11)	−0.0202 (11)
C6	0.0601 (15)	0.0640 (15)	0.0467 (13)	0.0033 (12)	−0.0229 (12)	−0.0197 (12)
C12	0.0558 (15)	0.0681 (15)	0.0490 (14)	0.0056 (12)	−0.0149 (12)	−0.0274 (12)
C13	0.0656 (16)	0.0634 (15)	0.0600 (16)	0.0144 (12)	−0.0203 (13)	−0.0248 (13)
C2	0.0734 (18)	0.0867 (19)	0.0599 (16)	0.0316 (14)	−0.0365 (14)	−0.0406 (14)
C3	0.0576 (16)	0.098 (2)	0.0593 (16)	0.0136 (14)	−0.0231 (13)	−0.0423 (15)

Geometric parameters (Å, º)

O1—C1	1.241 (3)	C8—H8	0.9300
O3—C9	1.362 (3)	C11—C10	1.377 (3)
O3—C13	1.424 (3)	C11—C12	1.379 (3)
O2—C10	1.355 (2)	C11—H11	0.9300
O2—H2	0.8200	C7—C12	1.396 (3)
N1—C1	1.331 (3)	C7—C6	1.462 (3)
N1—N2	1.387 (2)	C6—H6	0.9300
N1—H1	0.8600	C12—H12	0.9300
N2—C4	1.288 (3)	C13—H13A	0.9600
C9—C8	1.378 (3)	C13—H13B	0.9600
C9—C10	1.406 (3)	C13—H13C	0.9600
C5—C6	1.327 (3)	C2—C3	1.493 (3)
C5—C4	1.451 (3)	C2—H2A	0.9700
C5—H5	0.9300	C2—H2B	0.9700
C1—C2	1.480 (3)	C3—H3A	0.9700
C4—C3	1.486 (3)	C3—H3B	0.9700
C8—C7	1.394 (3)
C9—O3—C13	117.98 (17)	O2—C10—C11	124.3 (2)
C10—O2—H2	109.5	O2—C10—C9	116.1 (2)
C1—N1—N2	127.3 (2)	C11—C10—C9	119.54 (19)
C1—N1—H1	116.4	C5—C6—C7	127.7 (2)
N2—N1—H1	116.4	C5—C6—H6	116.1
C4—N2—N1	117.42 (18)	C7—C6—H6	116.1
O3—C9—C8	126.0 (2)	C11—C12—C7	120.5 (2)
O3—C9—C10	115.23 (18)	C11—C12—H12	119.8
C8—C9—C10	118.8 (2)	C7—C12—H12	119.8
C6—C5—C4	126.4 (2)	O3—C13—H13A	109.5
C6—C5—H5	116.8	O3—C13—H13B	109.5
C4—C5—H5	116.8	H13A—C13—H13B	109.5
O1—C1—N1	120.4 (2)	O3—C13—H13C	109.5
O1—C1—C2	123.3 (2)	H13A—C13—H13C	109.5
N1—C1—C2	116.36 (19)	H13B—C13—H13C	109.5
N2—C4—C5	115.5 (2)	C1—C2—C3	114.4 (2)
N2—C4—C3	122.97 (19)	C1—C2—H2A	108.7
C5—C4—C3	121.5 (2)	C3—C2—H2A	108.7
C9—C8—C7	122.0 (2)	C1—C2—H2B	108.7
C9—C8—H8	119.0	C3—C2—H2B	108.7
C7—C8—H8	119.0	H2A—C2—H2B	107.6
C10—C11—C12	121.0 (2)	C4—C3—C2	113.3 (2)
C10—C11—H11	119.5	C4—C3—H3A	108.9
C12—C11—H11	119.5	C2—C3—H3A	108.9
C8—C7—C12	118.02 (19)	C4—C3—H3B	108.9
C8—C7—C6	118.9 (2)	C2—C3—H3B	108.9
C12—C7—C6	123.1 (2)	H3A—C3—H3B	107.7
C1—N1—N2—C4	−12.5 (4)	O3—C9—C10—O2	−3.3 (3)
C13—O3—C9—C8	0.8 (3)	C8—C9—C10—O2	176.6 (2)
C13—O3—C9—C10	−179.3 (2)	O3—C9—C10—C11	176.6 (2)
N2—N1—C1—O1	−177.3 (2)	C8—C9—C10—C11	−3.5 (4)
N2—N1—C1—C2	1.2 (4)	C4—C5—C6—C7	−177.5 (2)
N1—N2—C4—C5	−177.97 (19)	C8—C7—C6—C5	177.4 (3)
N1—N2—C4—C3	−1.5 (3)	C12—C7—C6—C5	0.0 (4)
C6—C5—C4—N2	−176.7 (3)	C10—C11—C12—C7	0.2 (4)
C6—C5—C4—C3	6.8 (4)	C8—C7—C12—C11	−2.2 (4)
O3—C9—C8—C7	−178.7 (2)	C6—C7—C12—C11	175.2 (2)
C10—C9—C8—C7	1.4 (4)	O1—C1—C2—C3	−159.6 (3)
C9—C8—C7—C12	1.4 (4)	N1—C1—C2—C3	21.9 (4)
C9—C8—C7—C6	−176.1 (2)	N2—C4—C3—C2	23.8 (4)
C12—C11—C10—O2	−177.4 (2)	C5—C4—C3—C2	−160.0 (2)
C12—C11—C10—C9	2.7 (4)	C1—C2—C3—C4	−32.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1^i	0.82	1.86	2.671 (2)	168
N1—H1···O1^ii	0.86	2.02	2.875 (3)	170
C13—H13A···O2^iii	0.96	2.51	3.465 (3)	172
C13—H13C···O2^iv	0.96	2.57	3.489 (4)	159

Symmetry codes: (i) x−1, y, z−1; (ii) −x+1, −y+2, −z+2; (iii) −x+1, −y+1, −z; (iv) x+1, y, z.