Crystal structure of 4-(4-chloro­phen­yl)-6-(morpholin-4-yl)pyridazin-3(2H)-one

In the crystal, pairs of centrosymmetrically related mol­ecules are linked into dimers via N—H...O hydrogen bonds, forming (8) ring motifs. The dimers are connected via C—H...O and C—H...Cl hydrogen bonds, forming a three-dimensional network·Semi-empirical mol­ecular orbital calculations were carried out using the AM1 method.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.039
• wR factor = 0.106
• Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O2     --  C12     ..        5.1 su
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      7.352 Check

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size ....       0.80 mm
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

4-(4-Chlorophenyl)-6-(morpholin-4-yl)pyridazin-3(2H)-one

Crystal data

C14H14ClN3O2	F(000) = 608
Mr = 291.73	Dx = 1.399 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11553 reflections
a = 13.0977 (9) Å	θ = 1.6–28.0°
b = 7.4932 (4) Å	µ = 0.28 mm^−1
c = 14.1123 (9) Å	T = 296 K
β = 90.149 (5)°	Prism, yellow
V = 1385.03 (15) Å^3	0.80 × 0.38 × 0.08 mm
Z = 4

Data collection

Stoe IPDS 2 diffractometer	2868 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2267 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.028
Detector resolution: 6.67 pixels mm^-1	θmax = 26.5°, θmin = 1.6°
ω scans	h = −16→16
Absorption correction: integration (XRED-32; Stoe & Cie, 2002)	k = −9→9
Tmin = 0.880, Tmax = 0.978	l = −17→17
8760 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.106	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0578P)^2 + 0.1445P] where P = (Fo^2 + 2Fc^2)/3
2868 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.14 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

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 on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
Cl1	0.16215 (4)	0.21784 (11)	0.00258 (4)	0.0999 (2)
O1	0.42246 (7)	0.04185 (14)	0.40107 (6)	0.0472 (3)
O2	0.99398 (9)	0.3320 (2)	0.22281 (11)	0.0764 (5)
N1	0.58954 (8)	0.10751 (17)	0.41972 (8)	0.0454 (4)
N2	0.68499 (9)	0.16004 (17)	0.39371 (8)	0.0465 (4)
N3	0.78867 (9)	0.28188 (18)	0.27895 (9)	0.0499 (4)
C1	0.42580 (10)	0.17384 (18)	0.20628 (9)	0.0394 (4)
C2	0.43734 (11)	0.1304 (2)	0.11136 (10)	0.0500 (5)
C3	0.35657 (13)	0.1423 (2)	0.04893 (11)	0.0585 (5)
C4	0.26364 (12)	0.1993 (2)	0.08154 (11)	0.0563 (5)
C5	0.24891 (11)	0.2423 (2)	0.17507 (12)	0.0534 (5)
C6	0.33006 (10)	0.2283 (2)	0.23759 (10)	0.0455 (4)
C7	0.51501 (10)	0.16802 (18)	0.27082 (9)	0.0382 (4)
C8	0.50364 (10)	0.10152 (19)	0.36713 (9)	0.0393 (4)
C9	0.69357 (10)	0.21801 (19)	0.30668 (10)	0.0423 (4)
C10	0.60866 (10)	0.22402 (19)	0.24347 (10)	0.0427 (4)
C11	0.87216 (12)	0.2561 (3)	0.34556 (13)	0.0625 (6)
C12	0.96240 (13)	0.3681 (3)	0.31683 (15)	0.0724 (7)
C13	0.91285 (13)	0.3718 (4)	0.16077 (15)	0.0835 (8)
C14	0.81944 (13)	0.2585 (3)	0.18073 (14)	0.0745 (7)
H1	0.58330	0.07350	0.47760	0.0550*
H2	0.50070	0.09260	0.08950	0.0600*
H3	0.36500	0.11210	−0.01450	0.0700*
H5	0.18530	0.28040	0.19610	0.0640*
H6	0.32050	0.25550	0.30120	0.0550*
H10	0.61770	0.26720	0.18230	0.0510*
H11A	0.89160	0.13120	0.34680	0.0750*
H11B	0.85030	0.28970	0.40870	0.0750*
H12A	0.94450	0.49330	0.32220	0.0870*
H12B	1.01870	0.34500	0.35990	0.0870*
H13A	0.93470	0.35190	0.09600	0.1000*
H13B	0.89500	0.49690	0.16710	0.1000*
H14A	0.76410	0.29350	0.13890	0.0890*
H14B	0.83490	0.13390	0.16890	0.0890*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0672 (3)	0.1570 (6)	0.0753 (3)	−0.0021 (3)	−0.0358 (2)	0.0166 (3)
O1	0.0438 (5)	0.0619 (6)	0.0358 (5)	−0.0068 (5)	0.0003 (4)	0.0016 (4)
O2	0.0386 (5)	0.0910 (10)	0.0996 (10)	0.0011 (6)	0.0060 (6)	0.0097 (8)
N1	0.0441 (6)	0.0552 (7)	0.0370 (6)	−0.0050 (5)	−0.0037 (4)	0.0043 (5)
N2	0.0401 (6)	0.0511 (7)	0.0482 (6)	−0.0027 (5)	−0.0062 (5)	0.0051 (5)
N3	0.0353 (6)	0.0576 (8)	0.0569 (7)	−0.0008 (5)	−0.0028 (5)	0.0103 (6)
C1	0.0399 (7)	0.0394 (7)	0.0390 (6)	−0.0022 (5)	−0.0027 (5)	0.0050 (5)
C2	0.0474 (8)	0.0604 (9)	0.0422 (7)	0.0042 (7)	0.0001 (6)	0.0033 (6)
C3	0.0631 (9)	0.0735 (11)	0.0389 (7)	−0.0033 (8)	−0.0075 (6)	0.0036 (7)
C4	0.0480 (8)	0.0671 (11)	0.0537 (8)	−0.0070 (7)	−0.0159 (6)	0.0131 (7)
C5	0.0378 (7)	0.0626 (10)	0.0598 (9)	0.0002 (6)	−0.0038 (6)	0.0085 (7)
C6	0.0405 (7)	0.0524 (8)	0.0437 (7)	−0.0010 (6)	−0.0017 (5)	0.0017 (6)
C7	0.0389 (6)	0.0372 (7)	0.0386 (7)	0.0030 (5)	−0.0018 (5)	0.0009 (5)
C8	0.0411 (6)	0.0404 (7)	0.0365 (6)	−0.0006 (5)	−0.0019 (5)	−0.0023 (5)
C9	0.0371 (6)	0.0403 (7)	0.0496 (7)	0.0024 (5)	−0.0029 (5)	0.0037 (6)
C10	0.0399 (7)	0.0441 (8)	0.0440 (7)	0.0039 (6)	−0.0010 (5)	0.0079 (6)
C11	0.0414 (8)	0.0720 (11)	0.0740 (11)	−0.0014 (7)	−0.0124 (7)	0.0149 (9)
C12	0.0418 (8)	0.0806 (13)	0.0947 (14)	−0.0067 (8)	−0.0117 (8)	0.0124 (11)
C13	0.0474 (9)	0.1222 (19)	0.0809 (13)	−0.0066 (10)	0.0089 (8)	0.0210 (13)
C14	0.0456 (9)	0.1111 (16)	0.0669 (11)	−0.0097 (9)	0.0074 (8)	0.0022 (11)

Geometric parameters (Å, º)

Cl1—C4	1.7379 (17)	C7—C8	1.4556 (18)
O1—C8	1.2500 (16)	C7—C10	1.3535 (19)
O2—C12	1.417 (3)	C9—C10	1.4246 (19)
O2—C13	1.407 (2)	C11—C12	1.506 (3)
N1—N2	1.3620 (16)	C13—C14	1.516 (3)
N1—C8	1.3470 (17)	C2—H2	0.9300
N2—C9	1.3079 (18)	C3—H3	0.9300
N3—C9	1.3915 (18)	C5—H5	0.9300
N3—C11	1.453 (2)	C6—H6	0.9300
N3—C14	1.455 (2)	C10—H10	0.9300
N1—H1	0.8600	C11—H11A	0.9700
C1—C2	1.3872 (19)	C11—H11B	0.9700
C1—C6	1.3918 (19)	C12—H12A	0.9700
C1—C7	1.4803 (18)	C12—H12B	0.9700
C2—C3	1.378 (2)	C13—H13A	0.9700
C3—C4	1.371 (2)	C13—H13B	0.9700
C4—C5	1.373 (2)	C14—H14A	0.9700
C5—C6	1.384 (2)	C14—H14B	0.9700
C12—O2—C13	108.69 (14)	N3—C14—C13	109.58 (16)
N2—N1—C8	128.84 (11)	C1—C2—H2	119.00
N1—N2—C9	115.48 (11)	C3—C2—H2	119.00
C9—N3—C11	116.43 (13)	C2—C3—H3	120.00
C9—N3—C14	118.48 (13)	C4—C3—H3	120.00
C11—N3—C14	112.98 (13)	C4—C5—H5	120.00
C8—N1—H1	116.00	C6—C5—H5	120.00
N2—N1—H1	116.00	C1—C6—H6	120.00
C2—C1—C7	119.96 (12)	C5—C6—H6	120.00
C2—C1—C6	118.42 (12)	C7—C10—H10	119.00
C6—C1—C7	121.58 (12)	C9—C10—H10	119.00
C1—C2—C3	121.12 (14)	N3—C11—H11A	110.00
C2—C3—C4	119.11 (14)	N3—C11—H11B	110.00
Cl1—C4—C3	119.21 (12)	C12—C11—H11A	110.00
Cl1—C4—C5	119.25 (12)	C12—C11—H11B	110.00
C3—C4—C5	121.54 (15)	H11A—C11—H11B	108.00
C4—C5—C6	119.06 (14)	O2—C12—H12A	109.00
C1—C6—C5	120.73 (13)	O2—C12—H12B	109.00
C8—C7—C10	117.86 (12)	C11—C12—H12A	109.00
C1—C7—C10	122.00 (12)	C11—C12—H12B	109.00
C1—C7—C8	120.14 (11)	H12A—C12—H12B	108.00
O1—C8—N1	120.72 (12)	O2—C13—H13A	109.00
O1—C8—C7	124.71 (12)	O2—C13—H13B	109.00
N1—C8—C7	114.57 (12)	C14—C13—H13A	109.00
N2—C9—N3	117.23 (12)	C14—C13—H13B	109.00
N3—C9—C10	120.73 (13)	H13A—C13—H13B	108.00
N2—C9—C10	121.98 (12)	N3—C14—H14A	110.00
C7—C10—C9	121.21 (13)	N3—C14—H14B	110.00
N3—C11—C12	109.97 (16)	C13—C14—H14A	110.00
O2—C12—C11	112.14 (16)	C13—C14—H14B	110.00
O2—C13—C14	111.97 (19)	H14A—C14—H14B	108.00
C13—O2—C12—C11	60.9 (2)	C7—C1—C6—C5	176.41 (13)
C12—O2—C13—C14	−61.1 (2)	C2—C1—C7—C10	39.3 (2)
C8—N1—N2—C9	2.5 (2)	C6—C1—C7—C10	−138.37 (15)
N2—N1—C8—C7	−2.9 (2)	C1—C2—C3—C4	0.5 (2)
N2—N1—C8—O1	176.78 (13)	C2—C3—C4—Cl1	178.98 (12)
N1—N2—C9—C10	−0.5 (2)	C2—C3—C4—C5	−0.9 (2)
N1—N2—C9—N3	176.65 (12)	C3—C4—C5—C6	0.3 (2)
C11—N3—C9—C10	−175.00 (15)	Cl1—C4—C5—C6	−179.64 (12)
C14—N3—C11—C12	51.2 (2)	C4—C5—C6—C1	0.9 (2)
C9—N3—C11—C12	−166.70 (15)	C1—C7—C8—O1	2.1 (2)
C11—N3—C9—N2	7.8 (2)	C10—C7—C8—O1	−178.24 (14)
C14—N3—C9—N2	147.76 (15)	C10—C7—C8—N1	1.46 (19)
C11—N3—C14—C13	−51.3 (2)	C8—C7—C10—C9	0.1 (2)
C14—N3—C9—C10	−35.0 (2)	C1—C7—C10—C9	179.78 (13)
C9—N3—C14—C13	167.46 (16)	C1—C7—C8—N1	−178.23 (12)
C2—C1—C7—C8	−141.00 (14)	N3—C9—C10—C7	−177.67 (13)
C7—C1—C2—C3	−177.11 (13)	N2—C9—C10—C7	−0.6 (2)
C6—C1—C2—C3	0.7 (2)	N3—C11—C12—O2	−55.9 (2)
C6—C1—C7—C8	41.30 (19)	O2—C13—C14—N3	56.5 (2)
C2—C1—C6—C5	−1.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.86	1.92	2.7705 (15)	170
C5—H5···O2^ii	0.93	2.56	3.4737 (19)	166
C6—H6···O1	0.93	2.51	2.9538 (17)	109
C10—H10···O1^iii	0.93	2.43	3.1614 (17)	136
C12—H12B···Cl1^iv	0.97	2.79	3.754 (2)	173

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