N-Benzoyl-N′-methyl-N′-(p-tolyl­sulfon­yl)hydrazine

The crystal structure of the title compound, C₁₅H₁₆N₂O₃S, contains chains running along the a axis which are formed via inter­molecular N—H...O hydrogen bonds. The side chain comprising the N–N–C(=O)–C sequence of atoms is planar to within 0.0172 (14) Å and the benzene rings are inclined at 33.09 (11)° to one another.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.044
• wR factor = 0.100
• Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.530
           From the CIF: _refine_ls_abs_structure_Flack_su    0.090
PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero .......       0.53
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.50
           From the CIF: _reflns_number_total               3176
           Count of symmetry unique reflns         1781
           Completeness (_total/calc)            178.33%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1395
           Fraction of Friedel pairs measured     0.783
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

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

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Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

N-Methyl-N-[(4-methylphenyl)sulfonyl]-N'-benzoylhydrazine

Crystal data

C15H16N2O3S	Dx = 1.358 Mg m^−3
Mr = 304.36	Melting point = 463–464 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3176 reflections
a = 9.839 (6) Å	θ = 3.1–27.5°
b = 10.937 (4) Å	µ = 0.23 mm^−1
c = 13.836 (8) Å	T = 173 K
V = 1488.9 (14) Å^3	Block, colourless
Z = 4	0.18 × 0.16 × 0.12 mm
F(000) = 640

Data collection

Bruker Nonius KappaCCD area-detector diffractometer	3176 independent reflections
Radiation source: fine-focus sealed tube	2603 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.00
ω and φ scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −12→12
Tmin = 0.960, Tmax = 0.973	k = −14→14
3176 measured reflections	l = −17→17

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.100	w = 1/[σ^2(Fo^2) + (0.038P)^2 + 0.72P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
3176 reflections	Δρmax = 0.19 e Å^−3
192 parameters	Δρmin = −0.30 e Å^−3
1 restraint	Absolute structure: Flack (1983), with 1404 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.53 (9)

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

	x	y	z	Uiso*/Ueq
S1	0.12238 (6)	0.43829 (5)	0.31179 (6)	0.03049 (16)
O1	0.29964 (17)	0.20139 (18)	0.15228 (16)	0.0359 (5)
O2	0.1546 (2)	0.33792 (18)	0.37406 (16)	0.0412 (5)
O3	0.20520 (17)	0.54613 (16)	0.3109 (2)	0.0421 (5)
N1	0.1324 (2)	0.38502 (18)	0.20008 (17)	0.0299 (5)
N2	0.0858 (2)	0.26515 (19)	0.18660 (18)	0.0311 (5)
H2	−0.0005	0.2465	0.1945	0.037*
C1	0.1787 (3)	0.1781 (2)	0.1608 (2)	0.0274 (5)
C2	0.1226 (3)	0.0535 (2)	0.14283 (19)	0.0264 (5)
C3	0.1977 (3)	−0.0251 (3)	0.0851 (2)	0.0352 (7)
H3	0.2818	0.0016	0.0588	0.042*
C4	0.1512 (3)	−0.1422 (3)	0.0653 (2)	0.0405 (7)
H4	0.2041	−0.1957	0.0264	0.049*
C5	0.0281 (3)	−0.1813 (3)	0.1021 (2)	0.0390 (7)
H5	−0.0044	−0.2611	0.0878	0.047*
C6	−0.0476 (3)	−0.1035 (3)	0.1599 (2)	0.0381 (7)
H6	−0.1320	−0.1303	0.1857	0.046*
C7	−0.0010 (3)	0.0132 (2)	0.1804 (2)	0.0327 (6)
H7	−0.0534	0.0660	0.2202	0.039*
C8	0.1013 (3)	0.4669 (3)	0.1196 (2)	0.0431 (8)
H8A	0.1354	0.4313	0.0593	0.052*
H8B	0.1449	0.5462	0.1305	0.052*
H8C	0.0026	0.4780	0.1150	0.052*
C9	−0.0452 (3)	0.4844 (2)	0.33594 (19)	0.0286 (6)
C10	−0.0814 (3)	0.6060 (2)	0.3224 (2)	0.0360 (6)
H10	−0.0187	0.6623	0.2951	0.043*
C11	−0.2106 (3)	0.6441 (2)	0.3495 (2)	0.0389 (7)
H11	−0.2350	0.7276	0.3418	0.047*
C12	−0.3044 (3)	0.5633 (3)	0.3875 (2)	0.0325 (6)
C13	−0.2675 (3)	0.4407 (2)	0.3965 (2)	0.0324 (6)
H13	−0.3319	0.3836	0.4207	0.039*
C14	−0.1391 (3)	0.4003 (2)	0.3711 (2)	0.0318 (6)
H14	−0.1154	0.3164	0.3776	0.038*
C15	−0.4417 (3)	0.6067 (3)	0.4210 (2)	0.0468 (8)
H15A	−0.4354	0.6924	0.4412	0.056*
H15B	−0.4718	0.5566	0.4757	0.056*
H15C	−0.5071	0.5993	0.3679	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0276 (3)	0.0267 (3)	0.0371 (4)	0.0003 (2)	−0.0027 (3)	−0.0026 (3)
O1	0.0211 (9)	0.0413 (11)	0.0453 (12)	0.0009 (8)	−0.0002 (8)	−0.0052 (9)
O2	0.0439 (12)	0.0373 (11)	0.0425 (12)	0.0100 (9)	−0.0107 (10)	0.0033 (9)
O3	0.0325 (10)	0.0343 (9)	0.0596 (13)	−0.0100 (7)	0.0021 (12)	−0.0094 (11)
N1	0.0276 (12)	0.0266 (11)	0.0356 (13)	−0.0016 (9)	0.0012 (10)	−0.0033 (10)
N2	0.0212 (10)	0.0293 (11)	0.0428 (14)	−0.0012 (8)	0.0008 (10)	−0.0052 (10)
C1	0.0219 (13)	0.0335 (14)	0.0268 (13)	0.0019 (10)	−0.0016 (11)	−0.0023 (11)
C2	0.0223 (12)	0.0322 (13)	0.0247 (13)	0.0017 (10)	−0.0036 (10)	−0.0029 (11)
C3	0.0242 (14)	0.0442 (16)	0.0373 (17)	0.0020 (11)	0.0031 (12)	−0.0066 (13)
C4	0.0409 (17)	0.0371 (16)	0.0434 (17)	0.0049 (13)	0.0031 (14)	−0.0114 (13)
C5	0.0401 (17)	0.0315 (15)	0.0455 (18)	0.0013 (12)	−0.0005 (14)	−0.0019 (13)
C6	0.0316 (15)	0.0377 (16)	0.0448 (18)	−0.0029 (12)	0.0029 (13)	0.0017 (13)
C7	0.0286 (13)	0.0313 (13)	0.0380 (16)	0.0040 (11)	0.0046 (12)	−0.0037 (12)
C8	0.0425 (18)	0.0456 (17)	0.0411 (18)	−0.0063 (13)	0.0024 (14)	0.0092 (14)
C9	0.0297 (13)	0.0258 (11)	0.0305 (16)	0.0006 (10)	0.0025 (11)	−0.0008 (10)
C10	0.0390 (14)	0.0252 (11)	0.0436 (18)	−0.0002 (10)	0.0083 (15)	0.0052 (14)
C11	0.0433 (17)	0.0267 (13)	0.0468 (19)	0.0082 (12)	0.0083 (13)	0.0067 (12)
C12	0.0337 (15)	0.0389 (14)	0.0250 (14)	0.0045 (11)	0.0022 (12)	0.0012 (12)
C13	0.0339 (14)	0.0306 (13)	0.0327 (15)	−0.0035 (11)	0.0058 (12)	0.0027 (11)
C14	0.0375 (15)	0.0239 (12)	0.0341 (15)	−0.0025 (11)	0.0026 (12)	0.0002 (12)
C15	0.0410 (18)	0.0562 (19)	0.0433 (19)	0.0124 (15)	0.0119 (15)	0.0070 (15)

Geometric parameters (Å, º)

S1—O2	1.431 (2)	C6—H6	0.9500
S1—O3	1.434 (1)	C7—H7	0.9500
S1—N1	1.655 (3)	C8—H8A	0.9800
S1—C9	1.756 (3)	C8—H8B	0.9800
O1—C1	1.223 (3)	C8—H8C	0.9800
N1—N2	1.401 (3)	C9—C10	1.389 (3)
N1—C8	1.461 (4)	C9—C14	1.392 (4)
N2—C1	1.367 (3)	C10—C11	1.390 (4)
N2—H2	0.8800	C10—H10	0.9500
C1—C2	1.491 (3)	C11—C12	1.381 (4)
C2—C3	1.387 (4)	C11—H11	0.9500
C2—C7	1.394 (4)	C12—C13	1.396 (4)
C3—C4	1.388 (4)	C12—C15	1.505 (4)
C3—H3	0.9500	C13—C14	1.384 (4)
C4—C5	1.381 (4)	C13—H13	0.9500
C4—H4	0.9500	C14—H14	0.9500
C5—C6	1.386 (4)	C15—H15A	0.9800
C5—H5	0.9500	C15—H15B	0.9800
C6—C7	1.385 (4)	C15—H15C	0.9800
O2—S1—O3	120.68 (14)	C2—C7—H7	119.9
O2—S1—N1	106.21 (13)	N1—C8—H8A	109.5
O3—S1—N1	104.37 (14)	N1—C8—H8B	109.5
O2—S1—C9	108.27 (13)	H8A—C8—H8B	109.5
O3—S1—C9	107.39 (11)	N1—C8—H8C	109.5
N1—S1—C9	109.54 (12)	H8A—C8—H8C	109.5
N2—N1—C8	113.8 (2)	H8B—C8—H8C	109.5
N2—N1—S1	115.75 (18)	C10—C9—C14	120.7 (2)
C8—N1—S1	118.92 (19)	C10—C9—S1	119.33 (19)
C1—N2—N1	117.9 (2)	C14—C9—S1	120.0 (2)
C1—N2—H2	121.1	C11—C10—C9	119.0 (2)
N1—N2—H2	121.1	C11—C10—H10	120.5
O1—C1—N2	122.1 (2)	C9—C10—H10	120.5
O1—C1—C2	122.3 (2)	C12—C11—C10	121.5 (2)
N2—C1—C2	115.6 (2)	C12—C11—H11	119.3
C3—C2—C7	118.9 (2)	C10—C11—H11	119.3
C3—C2—C1	117.8 (2)	C11—C12—C13	118.4 (2)
C7—C2—C1	123.3 (2)	C11—C12—C15	121.0 (3)
C2—C3—C4	120.7 (3)	C13—C12—C15	120.6 (3)
C2—C3—H3	119.7	C14—C13—C12	121.4 (2)
C4—C3—H3	119.7	C14—C13—H13	119.3
C5—C4—C3	120.2 (3)	C12—C13—H13	119.3
C5—C4—H4	119.9	C13—C14—C9	118.9 (2)
C3—C4—H4	119.9	C13—C14—H14	120.5
C4—C5—C6	119.6 (3)	C9—C14—H14	120.5
C4—C5—H5	120.2	C12—C15—H15A	109.5
C6—C5—H5	120.2	C12—C15—H15B	109.5
C7—C6—C5	120.4 (3)	H15A—C15—H15B	109.5
C7—C6—H6	119.8	C12—C15—H15C	109.5
C5—C6—H6	119.8	H15A—C15—H15C	109.5
C6—C7—C2	120.3 (3)	H15B—C15—H15C	109.5
C6—C7—H7	119.9
O2—S1—N1—N2	37.5 (2)	C5—C6—C7—C2	0.1 (4)
O3—S1—N1—N2	165.99 (17)	C3—C2—C7—C6	−0.1 (4)
C9—S1—N1—N2	−79.27 (19)	C1—C2—C7—C6	179.4 (3)
O2—S1—N1—C8	178.6 (2)	O2—S1—C9—C10	150.2 (2)
O3—S1—N1—C8	−52.9 (2)	O3—S1—C9—C10	18.4 (3)
C9—S1—N1—C8	61.8 (2)	N1—S1—C9—C10	−94.4 (2)
C8—N1—N2—C1	102.8 (3)	O2—S1—C9—C14	−27.8 (3)
S1—N1—N2—C1	−114.1 (2)	O3—S1—C9—C14	−159.6 (2)
N1—N2—C1—O1	2.2 (4)	N1—S1—C9—C14	87.6 (2)
N1—N2—C1—C2	−177.2 (2)	C14—C9—C10—C11	3.5 (4)
O1—C1—C2—C3	−22.0 (4)	S1—C9—C10—C11	−174.5 (2)
N2—C1—C2—C3	157.4 (3)	C9—C10—C11—C12	−1.5 (5)
O1—C1—C2—C7	158.5 (3)	C10—C11—C12—C13	−1.2 (4)
N2—C1—C2—C7	−22.1 (4)	C10—C11—C12—C15	177.1 (3)
C7—C2—C3—C4	−0.4 (4)	C11—C12—C13—C14	1.9 (4)
C1—C2—C3—C4	−179.9 (3)	C15—C12—C13—C14	−176.4 (3)
C2—C3—C4—C5	0.9 (5)	C12—C13—C14—C9	0.1 (4)
C3—C4—C5—C6	−0.9 (5)	C10—C9—C14—C13	−2.8 (4)
C4—C5—C6—C7	0.4 (5)	S1—C9—C14—C13	175.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1^i	0.88	2.13	2.879 (3)	143

Symmetry code: (i) x−1/2, −y+1/2, z.