Synthesis and crystal structure of N-(5-acetyl-4-methyl­pyrimidin-2-yl)benzene­sulfonamide

N-(5-Acetyl-4-methyl­pyrimidin-2-yl)benzene­sulfonamide was synthesized and structurally characterized. In the crystal, π–π inter­actions between the phenyl and pyrimidine groups of neighbouring mol­ecules form mol­ecular chains parallel to [010]. Adjacent chains are linked by N—H...N hydrogen-bonding inter­actions, resulting in a three-dimensional network.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.046
• wR factor = 0.125
• Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          5 Note

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          8 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          7 Report
PLAT168_ALERT_4_G The CIF-Embedded .res File Contains EXYZ Records          1 Report
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          1 Report
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          1 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          1 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        20% Note
PLAT480_ALERT_4_G Long H...A H-Bond Reported H6       ..O2       .       2.62 Ang.
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         84 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        409 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        3.6 Low
PLAT951_ALERT_5_G Calculated (ThMax) and CIF-Reported Kmax Differ           2 Units
PLAT957_ALERT_1_G Calculated (ThMax) and Actual (FCF) Kmax Differ           2 Units
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Info
PLAT992_ALERT_5_G Repd & Actual _reflns_number_gt Values Differ by          3 Check

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

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

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Computing details

Data collection: CrysAlis PRO 1.171.42.54a (Rigaku OD, 2022); cell refinement: CrysAlis PRO 1.171.42.54a (Rigaku OD, 2022); data reduction: CrysAlis PRO 1.171.42.54a (Rigaku OD, 2022); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/1 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020), ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: Mercury (Macrae et al., 2020).

N-(5-Acetyl-4-methylpyrimidin-2-yl)benzenesulfonamide

Crystal data

C13H13N3O3S	F(000) = 608
Mr = 291.32	Dx = 1.355 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.0699 (6) Å	Cell parameters from 5035 reflections
b = 14.7429 (6) Å	θ = 3.9–27.7°
c = 10.5212 (7) Å	µ = 0.24 mm^−1
β = 113.900 (7)°	T = 293 K
V = 1428.04 (16) Å^3	Block, orange
Z = 4	0.44 × 0.24 × 0.16 mm

Data collection

Rigaku SuperNova, Dual, Cu at home/near, Atlas diffractometer	2548 reflections with I > 2σ(I)
ω scans	Rint = 0.026
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2022)	θmax = 29.5°, θmin = 3.5°
Tmin = 0.484, Tmax = 1.000	h = −13→10
12642 measured reflections	k = −18→18
3532 independent reflections	l = −13→14

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.125	w = 1/[σ^2(Fo^2) + (0.0493P)^2 + 0.420P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
3532 reflections	Δρmax = 0.23 e Å^−3
216 parameters	Δρmin = −0.29 e Å^−3
84 restraints

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	Occ. (<1)
C1	0.5229 (2)	0.75192 (12)	0.26887 (19)	0.0461 (4)
C2	0.6205 (2)	0.76291 (14)	0.2086 (2)	0.0552 (5)
H2	0.630570	0.718727	0.150041	0.066*
C3	0.7033 (2)	0.84155 (15)	0.2374 (3)	0.0651 (6)
H3	0.768869	0.850929	0.196825	0.078*
C4	0.6886 (3)	0.90550 (15)	0.3257 (3)	0.0712 (7)
H4	0.746248	0.957279	0.346473	0.085*
C5	0.5901 (3)	0.89393 (15)	0.3833 (2)	0.0696 (6)
H5	0.579890	0.938259	0.441639	0.083*
C6	0.5065 (3)	0.81732 (14)	0.3555 (2)	0.0580 (5)
H6	0.439261	0.809307	0.394462	0.070*
C7	0.6186 (2)	0.52796 (12)	0.37144 (19)	0.0463 (4)
C8	0.8002 (2)	0.49089 (16)	0.3045 (2)	0.0579 (5)
C10	0.7564 (2)	0.40722 (14)	0.4752 (2)	0.0568 (5)
H10	0.780068	0.359996	0.539203	0.068*
C11	0.8767 (3)	0.5141 (2)	0.2123 (3)	0.0835 (8)
H11A	0.853870	0.469409	0.140165	0.125*
H11B	0.979663	0.514976	0.266457	0.125*
H11C	0.845364	0.572710	0.171410	0.125*
N1	0.50291 (19)	0.58192 (11)	0.35938 (18)	0.0508 (4)
N2	0.69070 (18)	0.54638 (11)	0.29291 (17)	0.0537 (4)
N3	0.64728 (17)	0.46152 (10)	0.46533 (16)	0.0496 (4)
O1	0.28821 (16)	0.67414 (10)	0.25840 (16)	0.0653 (4)
O2	0.39885 (17)	0.61859 (10)	0.10316 (14)	0.0621 (4)
S1	0.41467 (5)	0.65419 (3)	0.23421 (5)	0.04929 (17)
C9	0.8367 (2)	0.41647 (16)	0.3968 (2)	0.0600 (5)	0.591 (11)
C12	0.9420 (7)	0.3432 (4)	0.3990 (8)	0.0750 (19)	0.591 (11)
C13	0.9860 (17)	0.2756 (10)	0.5150 (18)	0.098 (4)	0.591 (11)
H13A	1.053800	0.233375	0.505298	0.148*	0.591 (11)
H13B	0.901665	0.243536	0.511702	0.148*	0.591 (11)
H13C	1.030623	0.306600	0.602434	0.148*	0.591 (11)
O3	0.9931 (8)	0.3397 (4)	0.3128 (8)	0.110 (2)	0.591 (11)
C9A	0.8367 (2)	0.41647 (16)	0.3968 (2)	0.0600 (5)	0.409 (11)
C12A	0.9727 (9)	0.3620 (7)	0.4306 (12)	0.079 (3)	0.409 (11)
C13A	0.990 (2)	0.2750 (12)	0.509 (3)	0.089 (4)	0.409 (11)
H13D	1.082486	0.248722	0.525215	0.133*	0.409 (11)
H13E	0.913988	0.233796	0.454891	0.133*	0.409 (11)
H13F	0.983594	0.286757	0.595831	0.133*	0.409 (11)
O3A	1.0616 (8)	0.3857 (7)	0.3876 (10)	0.106 (3)	0.409 (11)
H1	0.458 (2)	0.5700 (14)	0.409 (2)	0.054 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0557 (11)	0.0456 (9)	0.0403 (10)	0.0056 (8)	0.0228 (9)	0.0082 (7)
C2	0.0619 (13)	0.0559 (11)	0.0551 (12)	0.0062 (9)	0.0311 (10)	0.0070 (9)
C3	0.0567 (13)	0.0676 (14)	0.0760 (16)	0.0015 (10)	0.0320 (12)	0.0183 (11)
C4	0.0695 (15)	0.0511 (12)	0.0789 (17)	−0.0026 (10)	0.0157 (13)	0.0080 (11)
C5	0.0897 (18)	0.0535 (12)	0.0634 (14)	0.0051 (11)	0.0287 (13)	−0.0043 (10)
C6	0.0754 (15)	0.0552 (11)	0.0510 (12)	0.0089 (10)	0.0335 (11)	0.0040 (9)
C7	0.0469 (11)	0.0518 (10)	0.0433 (10)	0.0003 (8)	0.0215 (9)	0.0043 (7)
C8	0.0491 (12)	0.0804 (14)	0.0498 (12)	−0.0014 (10)	0.0258 (10)	0.0012 (10)
C10	0.0515 (12)	0.0632 (12)	0.0570 (12)	0.0109 (9)	0.0233 (10)	0.0133 (9)
C11	0.0691 (16)	0.125 (2)	0.0738 (17)	0.0090 (15)	0.0472 (14)	0.0168 (15)
N1	0.0595 (10)	0.0514 (9)	0.0521 (10)	0.0093 (7)	0.0336 (8)	0.0141 (7)
N2	0.0550 (10)	0.0635 (10)	0.0499 (10)	−0.0001 (8)	0.0289 (8)	0.0072 (7)
N3	0.0506 (9)	0.0558 (9)	0.0481 (9)	0.0081 (7)	0.0259 (8)	0.0112 (7)
O1	0.0542 (9)	0.0753 (9)	0.0733 (10)	0.0134 (7)	0.0331 (8)	0.0233 (8)
O2	0.0792 (11)	0.0595 (8)	0.0457 (8)	−0.0060 (7)	0.0234 (7)	0.0020 (6)
S1	0.0546 (3)	0.0506 (3)	0.0465 (3)	0.0042 (2)	0.0244 (2)	0.00978 (19)
C9	0.0466 (11)	0.0798 (14)	0.0577 (13)	0.0102 (10)	0.0254 (10)	0.0069 (10)
C12	0.045 (2)	0.101 (3)	0.084 (4)	0.011 (2)	0.030 (3)	0.006 (3)
C13	0.081 (6)	0.098 (5)	0.094 (6)	0.048 (5)	0.012 (5)	0.016 (5)
O3	0.096 (4)	0.128 (4)	0.144 (5)	0.037 (3)	0.087 (4)	0.017 (3)
C9A	0.0466 (11)	0.0798 (14)	0.0577 (13)	0.0102 (10)	0.0254 (10)	0.0069 (10)
C12A	0.054 (4)	0.105 (4)	0.077 (4)	0.025 (4)	0.025 (4)	0.001 (4)
C13A	0.072 (7)	0.107 (8)	0.086 (7)	0.025 (7)	0.032 (6)	−0.007 (7)
O3A	0.070 (4)	0.144 (6)	0.127 (6)	0.026 (4)	0.062 (4)	0.009 (4)

Geometric parameters (Å, º)

C1—C2	1.378 (3)	C10—C9	1.376 (3)
C1—C6	1.382 (3)	C10—H10	0.9300
C1—S1	1.7538 (19)	C11—H11A	0.9600
C2—C3	1.388 (3)	C11—H11B	0.9600
C2—H2	0.9300	C11—H11C	0.9600
C3—C4	1.373 (3)	N1—S1	1.6465 (16)
C3—H3	0.9300	N1—H1	0.83 (2)
C4—C5	1.367 (3)	O1—S1	1.4267 (15)
C4—H4	0.9300	O2—S1	1.4226 (15)
C5—C6	1.368 (3)	C9—C12	1.507 (4)
C5—H5	0.9300	C12—O3	1.211 (5)
C6—H6	0.9300	C12—C13	1.497 (6)
C7—N2	1.330 (2)	C13—H13A	0.9600
C7—N3	1.337 (2)	C13—H13B	0.9600
C7—N1	1.374 (2)	C13—H13C	0.9600
C8—N2	1.338 (3)	C9A—C12A	1.501 (5)
C8—C9A	1.412 (3)	C12A—O3A	1.207 (5)
C8—C9	1.412 (3)	C12A—C13A	1.495 (6)
C8—C11	1.502 (3)	C13A—H13D	0.9600
C10—N3	1.329 (2)	C13A—H13E	0.9600
C10—C9A	1.376 (3)	C13A—H13F	0.9600
C2—C1—C6	121.33 (19)	C7—N1—S1	127.69 (14)
C2—C1—S1	120.01 (15)	C7—N1—H1	118.2 (14)
C6—C1—S1	118.66 (15)	S1—N1—H1	112.6 (15)
C1—C2—C3	118.4 (2)	C7—N2—C8	117.10 (17)
C1—C2—H2	120.8	C10—N3—C7	115.02 (17)
C3—C2—H2	120.8	O2—S1—O1	119.43 (10)
C4—C3—C2	120.1 (2)	O2—S1—N1	110.41 (9)
C4—C3—H3	120.0	O1—S1—N1	102.84 (9)
C2—C3—H3	120.0	O2—S1—C1	108.71 (9)
C5—C4—C3	120.8 (2)	O1—S1—C1	108.55 (9)
C5—C4—H4	119.6	N1—S1—C1	106.06 (9)
C3—C4—H4	119.6	C10—C9—C8	115.92 (19)
C4—C5—C6	120.2 (2)	C10—C9—C12	120.0 (3)
C4—C5—H5	119.9	C8—C9—C12	123.6 (3)
C6—C5—H5	119.9	O3—C12—C13	120.4 (5)
C5—C6—C1	119.3 (2)	O3—C12—C9	121.9 (4)
C5—C6—H6	120.3	C13—C12—C9	117.6 (5)
C1—C6—H6	120.3	C12—C13—H13A	109.5
N2—C7—N3	126.86 (17)	C12—C13—H13B	109.5
N2—C7—N1	118.71 (17)	H13A—C13—H13B	109.5
N3—C7—N1	114.43 (16)	C12—C13—H13C	109.5
N2—C8—C9A	120.86 (18)	H13A—C13—H13C	109.5
N2—C8—C9	120.86 (18)	H13B—C13—H13C	109.5
N2—C8—C11	114.9 (2)	C10—C9A—C8	115.92 (19)
C9A—C8—C11	124.2 (2)	C10—C9A—C12A	120.4 (3)
C9—C8—C11	124.2 (2)	C8—C9A—C12A	122.5 (3)
N3—C10—C9A	124.15 (19)	O3A—C12A—C13A	121.1 (5)
N3—C10—C9	124.15 (19)	O3A—C12A—C9A	120.1 (5)
N3—C10—H10	117.9	C13A—C12A—C9A	118.6 (6)
C9—C10—H10	117.9	C12A—C13A—H13D	109.5
C8—C11—H11A	109.5	C12A—C13A—H13E	109.5
C8—C11—H11B	109.5	H13D—C13A—H13E	109.5
H11A—C11—H11B	109.5	C12A—C13A—H13F	109.5
C8—C11—H11C	109.5	H13D—C13A—H13F	109.5
H11A—C11—H11C	109.5	H13E—C13A—H13F	109.5
H11B—C11—H11C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3^i	0.83 (2)	2.06 (2)	2.891 (2)	179 (2)
C6—H6···O2^ii	0.93	2.62	3.338 (3)	135
C10—H10···O1^i	0.93	2.54	3.243 (3)	133
C11—H11B···O3A	0.96	2.26	2.769 (7)	113
C13A—H13E···O1^iii	0.96	2.50	3.40 (3)	156

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+3/2, z+1/2; (iii) −x+1, y−1/2, −z+1/2.