2-[(2,4,6-Tri­methyl­benzene)­sulfon­yl]phthalazin-1(2H)-one: crystal structure, Hirshfeld surface analysis and computational study

Izuogu, D.C.; Asegbeloyin, J.N.; Jotani, M.M.; Tiekink, E.R.T.

doi:10.1107/S2056989020005101

2-[(2,4,6-Trimethylbenzene)sulfonyl]phthalazin-1(2H)-one: crystal structure, Hirshfeld surface analysis and computational study

D. C. Izuogu, J. N. Asegbeloyin, M. M. Jotani and E. R. T. Tiekink

The molecule in the title crystal has the shape of the letter V with the dihedral angle between the phthalazin-1-one and mesityl residues being 83.26 (4)°. Molecules assemble into a linear, supramolecular tape by phthalazinone-C₆-C—H

O(sulfoxide) and π(phthalazinone-N₂C₄)–π(phthalazinone-C₆) stacking interactions.

Keywords: crystal structure; phthalazinone; Hirshfeld surface analysis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989020005101/lh5956sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989020005101/lh5956Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989020005101/lh5956Isup3.cml Supplementary material

CCDC reference: 1996401

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R factor = 0.048
wR factor = 0.122
Data-to-parameter ratio = 28.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.651 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         41 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          5 Note

Alert level G
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        557 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         16 Info

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

   0 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
   3 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

Computing details top

Data collection: APEX2 (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

2-[(2,4,6-Trimethylbenzene)sulfonyl]phthalazin-1(2H)-one top

Crystal data top

C₁₇H₁₆N₂O₃S	Z = 2
M_r = 328.38	F(000) = 344
Triclinic, P1	D_x = 1.455 Mg m⁻³
a = 7.9782 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.1711 (5) Å	Cell parameters from 5241 reflections
c = 12.6661 (7) Å	θ = 2.7–34.7°
α = 92.214 (2)°	µ = 0.23 mm⁻¹
β = 93.423 (1)°	T = 100 K
γ = 114.274 (1)°	Prism, colourless
V = 749.55 (7) Å³	0.38 × 0.12 × 0.08 mm

Data collection top

Bruker APEXII CCD diffractometer	4625 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.027
ω scans	θ_max = 34.9°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.924, T_max = 1.000	k = −13→7
11665 measured reflections	l = −19→19
5913 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0579P)² + 0.3671P] where P = (F_o² + 2F_c²)/3
5913 reflections	(Δ/σ)_max < 0.001
211 parameters	Δρ_max = 0.59 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.52952 (4)	0.91549 (4)	0.73039 (2)	0.00972 (8)
O1	0.70758 (13)	0.91524 (14)	0.72487 (8)	0.01414 (19)
O2	0.51875 (14)	1.07825 (13)	0.76724 (7)	0.01422 (19)
O3	0.45530 (14)	0.53580 (14)	0.72961 (7)	0.01357 (19)
N1	0.42015 (15)	0.76225 (15)	0.82277 (8)	0.0107 (2)
N2	0.36966 (17)	0.83676 (16)	0.90820 (9)	0.0138 (2)
C1	0.38648 (17)	0.82486 (17)	0.61201 (9)	0.0097 (2)
C2	0.44783 (17)	0.75451 (17)	0.52613 (10)	0.0103 (2)
C3	0.32852 (18)	0.69064 (18)	0.43396 (10)	0.0116 (2)
H3	0.367189	0.643377	0.375142	0.014*
C4	0.15518 (18)	0.69371 (18)	0.42516 (10)	0.0126 (2)
C5	0.09886 (18)	0.76139 (19)	0.51177 (10)	0.0133 (2)
H5	−0.020289	0.761710	0.506665	0.016*
C6	0.21077 (18)	0.82878 (18)	0.60579 (10)	0.0116 (2)
C7	0.63166 (18)	0.7437 (2)	0.52408 (11)	0.0141 (2)
H7A	0.636640	0.683730	0.456594	0.021*
H7B	0.647194	0.675014	0.582699	0.021*
H7C	0.730720	0.865470	0.531622	0.021*
C8	0.0315 (2)	0.6274 (2)	0.32396 (11)	0.0190 (3)
H8A	−0.094563	0.608096	0.337969	0.028*
H8B	0.032099	0.513741	0.296720	0.028*
H8C	0.076289	0.717057	0.271317	0.028*
C9	0.1341 (2)	0.9043 (2)	0.69211 (11)	0.0190 (3)
H9A	0.184991	1.035634	0.691039	0.028*
H9B	0.168371	0.871735	0.761207	0.028*
H9C	−0.000599	0.854423	0.680026	0.028*
C10	0.40551 (17)	0.58589 (17)	0.80886 (10)	0.0099 (2)
C11	0.32443 (17)	0.47264 (18)	0.89581 (10)	0.0106 (2)
C12	0.30524 (18)	0.29500 (18)	0.89276 (10)	0.0132 (2)
H12	0.343082	0.246095	0.834285	0.016*
C13	0.23047 (19)	0.19062 (19)	0.97587 (11)	0.0153 (3)
H13	0.216814	0.069423	0.974185	0.018*
C14	0.17479 (19)	0.2621 (2)	1.06236 (11)	0.0160 (3)
H14	0.123129	0.189023	1.118763	0.019*
C15	0.19460 (19)	0.4382 (2)	1.06607 (11)	0.0154 (3)
H15	0.157015	0.486375	1.124986	0.018*
C16	0.27053 (18)	0.54625 (18)	0.98247 (10)	0.0118 (2)
C17	0.2996 (2)	0.73194 (19)	0.98264 (10)	0.0145 (2)
H17	0.264466	0.781298	1.042086	0.017*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.00989 (13)	0.01011 (14)	0.00894 (13)	0.00401 (11)	0.00008 (10)	0.00083 (10)
O1	0.0094 (4)	0.0174 (5)	0.0147 (4)	0.0047 (4)	0.0002 (3)	0.0018 (4)
O2	0.0193 (5)	0.0103 (4)	0.0128 (4)	0.0061 (4)	0.0007 (4)	−0.0004 (3)
O3	0.0168 (5)	0.0153 (5)	0.0105 (4)	0.0083 (4)	0.0033 (3)	0.0004 (3)
N1	0.0139 (5)	0.0110 (5)	0.0083 (4)	0.0060 (4)	0.0022 (4)	0.0010 (4)
N2	0.0203 (6)	0.0139 (5)	0.0094 (4)	0.0093 (5)	0.0019 (4)	−0.0013 (4)
C1	0.0105 (5)	0.0107 (5)	0.0082 (5)	0.0046 (4)	0.0002 (4)	0.0007 (4)
C2	0.0109 (5)	0.0109 (5)	0.0106 (5)	0.0054 (4)	0.0030 (4)	0.0023 (4)
C3	0.0139 (5)	0.0121 (6)	0.0094 (5)	0.0059 (5)	0.0025 (4)	0.0006 (4)
C4	0.0121 (5)	0.0128 (6)	0.0113 (5)	0.0035 (5)	−0.0001 (4)	0.0009 (4)
C5	0.0107 (5)	0.0176 (6)	0.0130 (5)	0.0073 (5)	0.0002 (4)	0.0008 (5)
C6	0.0115 (5)	0.0143 (6)	0.0107 (5)	0.0071 (5)	0.0010 (4)	0.0005 (4)
C7	0.0118 (5)	0.0181 (6)	0.0151 (5)	0.0086 (5)	0.0035 (5)	0.0016 (5)
C8	0.0167 (6)	0.0226 (7)	0.0134 (6)	0.0050 (6)	−0.0036 (5)	−0.0036 (5)
C9	0.0186 (6)	0.0309 (8)	0.0138 (6)	0.0172 (6)	0.0002 (5)	−0.0043 (5)
C10	0.0091 (5)	0.0112 (5)	0.0094 (5)	0.0045 (4)	−0.0012 (4)	−0.0005 (4)
C11	0.0100 (5)	0.0122 (6)	0.0094 (5)	0.0044 (4)	0.0004 (4)	0.0010 (4)
C12	0.0140 (6)	0.0125 (6)	0.0132 (5)	0.0059 (5)	0.0001 (4)	−0.0003 (4)
C13	0.0143 (6)	0.0119 (6)	0.0185 (6)	0.0041 (5)	0.0009 (5)	0.0038 (5)
C14	0.0135 (6)	0.0188 (7)	0.0149 (6)	0.0052 (5)	0.0024 (5)	0.0069 (5)
C15	0.0148 (6)	0.0207 (7)	0.0116 (5)	0.0079 (5)	0.0031 (5)	0.0020 (5)
C16	0.0114 (5)	0.0137 (6)	0.0108 (5)	0.0060 (5)	0.0003 (4)	0.0006 (4)
C17	0.0195 (6)	0.0167 (6)	0.0103 (5)	0.0104 (5)	0.0025 (5)	−0.0008 (4)

Geometric parameters (Å, º) top

S1—O1	1.4273 (10)	C7—H7C	0.9800
S1—O2	1.4300 (10)	C8—H8A	0.9800
S1—N1	1.7422 (11)	C8—H8B	0.9800
S1—C1	1.7646 (12)	C8—H8C	0.9800
O3—C10	1.2175 (15)	C9—H9A	0.9800
N1—N2	1.3808 (15)	C9—H9B	0.9800
N1—C10	1.4003 (17)	C9—H9C	0.9800
N2—C17	1.2911 (18)	C10—C11	1.4694 (18)
C1—C6	1.4130 (18)	C11—C12	1.3943 (19)
C1—C2	1.4142 (17)	C11—C16	1.4034 (18)
C2—C3	1.3975 (18)	C12—C13	1.3847 (19)
C2—C7	1.5066 (18)	C12—H12	0.9500
C3—C4	1.3913 (19)	C13—C14	1.400 (2)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.3883 (18)	C14—C15	1.380 (2)
C4—C8	1.5055 (19)	C14—H14	0.9500
C5—C6	1.3917 (18)	C15—C16	1.4059 (19)
C5—H5	0.9500	C15—H15	0.9500
C6—C9	1.5125 (18)	C16—C17	1.438 (2)
C7—H7A	0.9800	C17—H17	0.9500
C7—H7B	0.9800

O1—S1—O2	118.39 (6)	C4—C8—H8B	109.5
O1—S1—N1	106.22 (6)	H8A—C8—H8B	109.5
O2—S1—N1	104.37 (6)	C4—C8—H8C	109.5
O1—S1—C1	112.48 (6)	H8A—C8—H8C	109.5
O2—S1—C1	110.28 (6)	H8B—C8—H8C	109.5
N1—S1—C1	103.58 (6)	C6—C9—H9A	109.5
N2—N1—C10	126.97 (11)	C6—C9—H9B	109.5
N2—N1—S1	113.93 (9)	H9A—C9—H9B	109.5
C10—N1—S1	118.89 (8)	C6—C9—H9C	109.5
C17—N2—N1	116.47 (12)	H9A—C9—H9C	109.5
C6—C1—C2	121.56 (11)	H9B—C9—H9C	109.5
C6—C1—S1	117.50 (9)	O3—C10—N1	120.86 (12)
C2—C1—S1	120.94 (10)	O3—C10—C11	124.94 (12)
C3—C2—C1	117.37 (12)	N1—C10—C11	114.19 (11)
C3—C2—C7	116.62 (11)	C12—C11—C16	120.62 (12)
C1—C2—C7	126.01 (11)	C12—C11—C10	120.00 (11)
C4—C3—C2	122.42 (12)	C16—C11—C10	119.36 (12)
C4—C3—H3	118.8	C13—C12—C11	119.31 (12)
C2—C3—H3	118.8	C13—C12—H12	120.3
C5—C4—C3	118.48 (12)	C11—C12—H12	120.3
C5—C4—C8	120.39 (12)	C12—C13—C14	120.60 (13)
C3—C4—C8	121.12 (12)	C12—C13—H13	119.7
C4—C5—C6	122.33 (12)	C14—C13—H13	119.7
C4—C5—H5	118.8	C15—C14—C13	120.31 (13)
C6—C5—H5	118.8	C15—C14—H14	119.8
C5—C6—C1	117.83 (11)	C13—C14—H14	119.8
C5—C6—C9	116.57 (12)	C14—C15—C16	119.85 (13)
C1—C6—C9	125.58 (12)	C14—C15—H15	120.1
C2—C7—H7A	109.5	C16—C15—H15	120.1
C2—C7—H7B	109.5	C11—C16—C15	119.30 (13)
H7A—C7—H7B	109.5	C11—C16—C17	117.99 (12)
C2—C7—H7C	109.5	C15—C16—C17	122.69 (12)
H7A—C7—H7C	109.5	N2—C17—C16	125.01 (12)
H7B—C7—H7C	109.5	N2—C17—H17	117.5
C4—C8—H8A	109.5	C16—C17—H17	117.5

O1—S1—N1—N2	120.33 (10)	C2—C1—C6—C5	−0.2 (2)
O2—S1—N1—N2	−5.52 (11)	S1—C1—C6—C5	178.53 (10)
C1—S1—N1—N2	−120.99 (10)	C2—C1—C6—C9	−178.71 (14)
O1—S1—N1—C10	−54.70 (11)	S1—C1—C6—C9	0.02 (19)
O2—S1—N1—C10	179.45 (10)	N2—N1—C10—O3	−179.88 (12)
C1—S1—N1—C10	63.98 (11)	S1—N1—C10—O3	−5.57 (17)
C10—N1—N2—C17	−0.8 (2)	N2—N1—C10—C11	0.98 (18)
S1—N1—N2—C17	−175.38 (10)	S1—N1—C10—C11	175.29 (9)
O1—S1—C1—C6	−176.04 (10)	O3—C10—C11—C12	2.1 (2)
O2—S1—C1—C6	−41.49 (12)	N1—C10—C11—C12	−178.79 (11)
N1—S1—C1—C6	69.70 (11)	O3—C10—C11—C16	−179.23 (12)
O1—S1—C1—C2	2.71 (13)	N1—C10—C11—C16	−0.13 (17)
O2—S1—C1—C2	137.26 (11)	C16—C11—C12—C13	0.6 (2)
N1—S1—C1—C2	−111.55 (11)	C10—C11—C12—C13	179.29 (12)
C6—C1—C2—C3	0.74 (19)	C11—C12—C13—C14	−0.1 (2)
S1—C1—C2—C3	−177.95 (10)	C12—C13—C14—C15	−0.3 (2)
C6—C1—C2—C7	179.99 (13)	C13—C14—C15—C16	0.2 (2)
S1—C1—C2—C7	1.30 (19)	C12—C11—C16—C15	−0.75 (19)
C1—C2—C3—C4	−0.3 (2)	C10—C11—C16—C15	−179.40 (12)
C7—C2—C3—C4	−179.65 (12)	C12—C11—C16—C17	177.93 (12)
C2—C3—C4—C5	−0.6 (2)	C10—C11—C16—C17	−0.72 (18)
C2—C3—C4—C8	178.73 (13)	C14—C15—C16—C11	0.3 (2)
C3—C4—C5—C6	1.2 (2)	C14—C15—C16—C17	−178.29 (13)
C8—C4—C5—C6	−178.16 (13)	N1—N2—C17—C16	−0.2 (2)
C4—C5—C6—C1	−0.8 (2)	C11—C16—C17—N2	0.9 (2)
C4—C5—C6—C9	177.86 (14)	C15—C16—C17—N2	179.58 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2ⁱ	0.95	2.49	3.3395 (18)	149

Symmetry code: (i) x, y−1, z.

A summary of short interatomic contacts (Å) in (I)^a top

Contact	Distance	Symmetry operation
C10···C14	3.345 (2)	1 - x, 1 - y, 2 - z
C12···C16	3.351 (2)	1 - x, 1 - y, 2 - z
O1···H9C	2.58	1 + x, y, z
O1···H14	2.61	1 - x, 1 - y, 2 - z
O3···H8A	2.60	- x, 1 - y, 1 - z
C5···H7C	2.78	1 - x, 2 - y, 1 - z
C7···H5	2.61	1 + x, y, z
C10···H8A	2.79	- x, 1 - y, 1 - z
H12···H9A	2.20	x, -1 + y, z

Notes: (a) The interatomic distances are calculated in Crystal Explorer 17 (Turner et al., 2017) whereby the X—H bond lengths are adjusted to their neutron values; (b) these interactions correspond to conventional hydrogen bonds.

Percentage contributions to intermolecular contacts on the Hirshfeld surface calculated for (I) top

Contact	Percentage contribution
H···H	44.9
O···H/H···O	24.0
C···H/H···C	18.1
C···C	6.5
N···H/H··· N	4.0
C···O/O···C	1.1
C···N/N···C	0.7
N···N	0.4
C···S/S···C	0.2

A summary of interaction energies (kJ mol^-1) calculated for (I) top

Contact	R (Å)	E_ele	E_pol	E_dis	E_rep	E_tot
Cg(N₂C₄)···Cg(C₆)ⁱ +
Cg(C₆)···Cg(C₆)ⁱ +	8.12	-28.9	-5.0	-64.7	48.2	-60.8
O1···H14ⁱ
C5···H7Cⁱⁱ	7.84	-21.3	-5.5	-60.9	43.5	-52.8
O3 ···H8Aⁱⁱⁱ +
C10 ···H8Aⁱⁱⁱ	7.54	-10.7	-2.0	-56.8	32.6	-42.1
C12—H12···O2^iv +
H12···H9A^iv	8.17	-4.4	-4.6	-20.5	18.0	-14.8
O1···H9C^v +
C7···H5^v	7.98	-3.1	-2.0	-16.9	14.2	-10.6

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

A comparison of key geometric parameters (Å; °) for (I) and (II) top

N1—N2	1.3808 (15)	1.384 (2)
C10—O3	1.2175 (15	1.212 (3)
C10—N1	1.4003 (17)	1.406 (2)
C17—N2	1.2911 (18)	1.283 (2)
N2···O2	2.6631 (15)	2.6394 (19)
N2—N1—S1—O1	120.33 (10)	138.71 (12)
N2—N1—S1—O2	-5.52 (11)	9.59 (13)
N1—S1—C1—C2	-111.55 (11)	-103.95 (16)
N1—S1—C1—C6	69.70 (11)	76.49 (17)

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2-[(2,4,6-Tri­methyl­benzene)­sulfon­yl]phthalazin-1(2H)-one: crystal structure, Hirshfeld surface analysis and computational study

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2-[(2,4,6-Trimethylbenzene)sulfonyl]phthalazin-1(2H)-one: crystal structure, Hirshfeld surface analysis and computational study