Crystal structure and Hirshfeld surface analysis of ethyl 2-[5-(3-chloro­benz­yl)-6-oxo-3-phenyl-1,6-di­hydro­pyridazin-1-yl]acetate

In the title pyridazinone derivative, the unsubstituted phenyl ring and the pyridazine ring are inclined to each other, making a dihedral angle of 17.41 (13)°, whereas the Cl-substituted phenyl ring is nearly orthogonal to the pyridazine ring [88.19 (13)°], C₂₁H₁₉ClN₂O₃, contains one independent mol­ecule. C—H...O hydrogen bonds, weak C—H...π and weak offset π–π stacking inter­actions stabilize the packing.

checkCIF/PLATON results

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Datablock: I


Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O1       --C8       .        5.1 s.u.
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         C1 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C20 Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H15      ..O1       .       2.66 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     25.218 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      4.492 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          6 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size ....       0.88 mm
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.009 Degree
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   2 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 (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).

Ethyl 2-[5-(3-chlorobenzyl)-6-oxo-3-phenyl-1,6-dihydropyridazin-1-yl]acetate

Crystal data

C21H19ClN2O3	Z = 2
Mr = 382.83	F(000) = 400
Triclinic, P1	Dx = 1.339 Mg m^−3
a = 8.8410 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.3043 (12) Å	Cell parameters from 11025 reflections
c = 11.3610 (12) Å	θ = 3.0–31.4°
α = 94.801 (9)°	µ = 0.23 mm^−1
β = 103.596 (9)°	T = 296 K
γ = 106.905 (9)°	Prism, yellow
V = 949.6 (2) Å^3	0.88 × 0.53 × 0.19 mm

Data collection

Stoe IPDS 2 diffractometer	2058 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm^-1	Rint = 0.031
rotation method scans	θmax = 26.0°, θmin = 3.0°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −10→10
Tmin = 0.876, Tmax = 0.960	k = −12→12
9612 measured reflections	l = −14→14
3716 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)] = 0.047	H-atom parameters constrained
wR(F^2) = 0.127	w = 1/[σ^2(Fo^2) + (0.0666P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.91	(Δ/σ)max < 0.001
3716 reflections	Δρmax = 0.26 e Å^−3
245 parameters	Δρmin = −0.34 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
Cl1	0.29831 (14)	0.53925 (11)	−0.10674 (8)	0.1264 (4)
O3	0.72303 (19)	0.86361 (16)	0.93869 (13)	0.0654 (5)
O2	0.4976 (2)	0.87323 (18)	0.80559 (15)	0.0704 (5)
O1	0.6649 (2)	0.89797 (17)	0.57180 (15)	0.0725 (5)
N1	0.4130 (2)	0.57611 (18)	0.60996 (15)	0.0503 (5)
N2	0.5368 (2)	0.69655 (18)	0.62523 (15)	0.0542 (5)
C12	0.1658 (3)	0.4089 (2)	0.49033 (17)	0.0463 (5)
C11	0.3033 (3)	0.5381 (2)	0.50375 (17)	0.0462 (5)
C19	0.6111 (3)	0.8315 (2)	0.83046 (19)	0.0536 (6)
C10	0.3151 (3)	0.6166 (2)	0.40745 (18)	0.0507 (5)
H10	0.238158	0.583782	0.331377	0.061*
C9	0.4352 (3)	0.7377 (2)	0.42376 (19)	0.0528 (6)
C13	0.0216 (3)	0.3784 (2)	0.39727 (19)	0.0556 (6)
H13	0.012681	0.437926	0.340794	0.067*
C8	0.5539 (3)	0.7869 (2)	0.5427 (2)	0.0557 (6)
C5	0.3334 (3)	0.7688 (2)	0.2046 (2)	0.0602 (6)
C17	0.1752 (3)	0.3177 (2)	0.5723 (2)	0.0617 (6)
H17	0.270130	0.335520	0.636054	0.074*
C18	0.6531 (3)	0.7357 (2)	0.7459 (2)	0.0618 (6)
H18A	0.762208	0.780076	0.737838	0.074*
H18B	0.654649	0.653680	0.781667	0.074*
C14	−0.1095 (3)	0.2608 (3)	0.3867 (2)	0.0659 (7)
H14	−0.206077	0.242734	0.324506	0.079*
C6	0.3669 (3)	0.6883 (3)	0.1175 (2)	0.0693 (7)
H6	0.465811	0.669538	0.134709	0.083*
C15	−0.0967 (4)	0.1717 (3)	0.4678 (3)	0.0735 (7)
H15	−0.183752	0.091911	0.460255	0.088*
C7	0.4550 (3)	0.8283 (2)	0.3280 (2)	0.0659 (7)
H7A	0.565102	0.846300	0.318471	0.079*
H7B	0.444144	0.915570	0.356666	0.079*
C20	0.6983 (3)	0.9534 (3)	1.0330 (2)	0.0697 (7)
H20A	0.592464	0.912468	1.048073	0.084*
H20B	0.702185	1.041629	1.007747	0.084*
C16	0.0439 (4)	0.1999 (3)	0.5596 (3)	0.0749 (8)
H16	0.051884	0.138934	0.614912	0.090*
C1	0.2528 (4)	0.6351 (3)	0.0037 (2)	0.0752 (8)
C4	0.1844 (4)	0.7928 (3)	0.1767 (2)	0.0752 (8)
H4	0.160060	0.847345	0.234301	0.090*
C2	0.1061 (4)	0.6593 (3)	−0.0218 (3)	0.0839 (9)
H2	0.030067	0.622809	−0.097796	0.101*
C3	0.0711 (4)	0.7371 (3)	0.0646 (3)	0.0902 (9)
H3	−0.029726	0.752677	0.047719	0.108*
C21	0.8330 (5)	0.9709 (4)	1.1455 (3)	0.1279 (16)
H21A	0.936252	1.019422	1.131745	0.192*
H21B	0.834403	0.882260	1.164831	0.192*
H21C	0.815587	1.022374	1.212596	0.192*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.1545 (9)	0.1266 (8)	0.0925 (6)	0.0370 (7)	0.0468 (6)	−0.0221 (5)
O3	0.0619 (10)	0.0768 (11)	0.0468 (8)	0.0251 (9)	−0.0023 (8)	−0.0084 (7)
O2	0.0597 (11)	0.0818 (12)	0.0620 (10)	0.0286 (9)	0.0007 (8)	−0.0056 (8)
O1	0.0687 (11)	0.0536 (10)	0.0731 (11)	−0.0058 (9)	0.0156 (9)	−0.0070 (8)
N1	0.0517 (11)	0.0514 (11)	0.0437 (10)	0.0153 (9)	0.0090 (8)	0.0008 (8)
N2	0.0504 (11)	0.0545 (11)	0.0460 (10)	0.0091 (10)	0.0048 (8)	−0.0036 (8)
C12	0.0519 (13)	0.0456 (12)	0.0411 (11)	0.0144 (10)	0.0158 (10)	0.0004 (9)
C11	0.0502 (13)	0.0478 (12)	0.0386 (11)	0.0162 (11)	0.0100 (10)	0.0005 (9)
C19	0.0475 (13)	0.0558 (13)	0.0452 (12)	0.0093 (11)	0.0012 (10)	0.0008 (9)
C10	0.0563 (14)	0.0501 (13)	0.0401 (11)	0.0141 (11)	0.0086 (10)	0.0009 (9)
C9	0.0594 (14)	0.0458 (12)	0.0505 (12)	0.0126 (11)	0.0175 (11)	0.0015 (9)
C13	0.0589 (14)	0.0537 (13)	0.0475 (12)	0.0142 (12)	0.0098 (11)	−0.0004 (10)
C8	0.0573 (15)	0.0511 (13)	0.0525 (13)	0.0119 (12)	0.0145 (11)	−0.0035 (10)
C5	0.0752 (17)	0.0482 (13)	0.0541 (13)	0.0100 (12)	0.0218 (12)	0.0158 (10)
C17	0.0624 (16)	0.0636 (15)	0.0562 (13)	0.0174 (13)	0.0130 (12)	0.0126 (11)
C18	0.0541 (14)	0.0672 (15)	0.0505 (12)	0.0165 (12)	−0.0014 (11)	−0.0082 (11)
C14	0.0514 (15)	0.0637 (16)	0.0668 (15)	0.0067 (13)	0.0084 (12)	−0.0105 (13)
C6	0.0742 (18)	0.0634 (15)	0.0690 (16)	0.0162 (13)	0.0246 (14)	0.0100 (12)
C15	0.0699 (18)	0.0566 (16)	0.0838 (18)	0.0018 (13)	0.0295 (15)	−0.0022 (14)
C7	0.0793 (18)	0.0524 (14)	0.0592 (14)	0.0114 (12)	0.0179 (13)	0.0110 (11)
C20	0.0812 (19)	0.0734 (17)	0.0524 (13)	0.0277 (14)	0.0147 (13)	−0.0022 (12)
C16	0.091 (2)	0.0592 (16)	0.0750 (17)	0.0149 (16)	0.0318 (16)	0.0214 (13)
C1	0.095 (2)	0.0646 (16)	0.0622 (16)	0.0137 (16)	0.0299 (15)	0.0051 (12)
C4	0.089 (2)	0.0779 (18)	0.0639 (16)	0.0308 (16)	0.0244 (15)	0.0151 (13)
C2	0.092 (2)	0.085 (2)	0.0601 (16)	0.0142 (17)	0.0099 (16)	0.0108 (14)
C3	0.088 (2)	0.101 (2)	0.083 (2)	0.0356 (18)	0.0183 (17)	0.0193 (17)
C21	0.156 (3)	0.171 (4)	0.0489 (16)	0.091 (3)	−0.0186 (19)	−0.0337 (18)

Geometric parameters (Å, º)

Cl1—C1	1.724 (3)	C17—H17	0.9300
O3—C19	1.331 (2)	C18—H18A	0.9700
O3—C20	1.454 (3)	C18—H18B	0.9700
O2—C19	1.187 (3)	C14—C15	1.362 (4)
O1—C8	1.230 (3)	C14—H14	0.9300
N1—C11	1.304 (2)	C6—C1	1.391 (4)
N1—N2	1.362 (2)	C6—H6	0.9300
N2—C8	1.378 (3)	C15—C16	1.359 (4)
N2—C18	1.450 (3)	C15—H15	0.9300
C12—C17	1.383 (3)	C7—H7A	0.9700
C12—C13	1.385 (3)	C7—H7B	0.9700
C12—C11	1.487 (3)	C20—C21	1.484 (4)
C11—C10	1.420 (3)	C20—H20A	0.9700
C19—C18	1.502 (3)	C20—H20B	0.9700
C10—C9	1.347 (3)	C16—H16	0.9300
C10—H10	0.9300	C1—C2	1.360 (4)
C9—C8	1.447 (3)	C4—C3	1.378 (4)
C9—C7	1.500 (3)	C4—H4	0.9300
C13—C14	1.386 (3)	C2—C3	1.363 (4)
C13—H13	0.9300	C2—H2	0.9300
C5—C6	1.378 (3)	C3—H3	0.9300
C5—C4	1.380 (4)	C21—H21A	0.9600
C5—C7	1.503 (3)	C21—H21B	0.9600
C17—C16	1.384 (4)	C21—H21C	0.9600
C19—O3—C20	116.13 (18)	C13—C14—H14	120.1
C11—N1—N2	116.83 (18)	C5—C6—C1	120.0 (3)
N1—N2—C8	126.86 (17)	C5—C6—H6	120.0
N1—N2—C18	114.58 (19)	C1—C6—H6	120.0
C8—N2—C18	118.35 (19)	C16—C15—C14	119.7 (2)
C17—C12—C13	117.8 (2)	C16—C15—H15	120.1
C17—C12—C11	121.31 (19)	C14—C15—H15	120.1
C13—C12—C11	120.81 (19)	C9—C7—C5	114.18 (19)
N1—C11—C10	121.6 (2)	C9—C7—H7A	108.7
N1—C11—C12	116.04 (18)	C5—C7—H7A	108.7
C10—C11—C12	122.40 (17)	C9—C7—H7B	108.7
O2—C19—O3	125.0 (2)	C5—C7—H7B	108.7
O2—C19—C18	126.11 (19)	H7A—C7—H7B	107.6
O3—C19—C18	108.9 (2)	O3—C20—C21	106.6 (2)
C9—C10—C11	121.50 (19)	O3—C20—H20A	110.4
C9—C10—H10	119.3	C21—C20—H20A	110.4
C11—C10—H10	119.3	O3—C20—H20B	110.4
C10—C9—C8	118.4 (2)	C21—C20—H20B	110.4
C10—C9—C7	125.0 (2)	H20A—C20—H20B	108.6
C8—C9—C7	116.5 (2)	C15—C16—C17	121.1 (3)
C12—C13—C14	121.3 (2)	C15—C16—H16	119.4
C12—C13—H13	119.4	C17—C16—H16	119.4
C14—C13—H13	119.4	C2—C1—C6	120.6 (3)
O1—C8—N2	120.3 (2)	C2—C1—Cl1	119.6 (2)
O1—C8—C9	125.2 (2)	C6—C1—Cl1	119.8 (3)
N2—C8—C9	114.5 (2)	C3—C4—C5	120.9 (3)
C6—C5—C4	118.5 (2)	C3—C4—H4	119.6
C6—C5—C7	121.1 (3)	C5—C4—H4	119.6
C4—C5—C7	120.4 (2)	C1—C2—C3	119.7 (3)
C12—C17—C16	120.2 (2)	C1—C2—H2	120.1
C12—C17—H17	119.9	C3—C2—H2	120.1
C16—C17—H17	119.9	C2—C3—C4	120.3 (3)
N2—C18—C19	112.24 (19)	C2—C3—H3	119.9
N2—C18—H18A	109.2	C4—C3—H3	119.9
C19—C18—H18A	109.2	C20—C21—H21A	109.5
N2—C18—H18B	109.2	C20—C21—H21B	109.5
C19—C18—H18B	109.2	H21A—C21—H21B	109.5
H18A—C18—H18B	107.9	C20—C21—H21C	109.5
C15—C14—C13	119.8 (2)	H21A—C21—H21C	109.5
C15—C14—H14	120.1	H21B—C21—H21C	109.5

Hydrogen-bond geometry (Å, º)

Cg2 is the centroid of the C1–C6 phenyl ring

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O2^i	0.93	2.53	3.416 (3)	160
C7—H7B···O1^ii	0.97	2.54	3.485 (3)	164
C15—H15···O1^iii	0.93	2.66	3.474 (3)	147
C20—H20B···Cg2^iv	0.97	2.81	3.759 (3)	165

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