Crystal structure of (E)-4-methyl-N-{2-[2-(4-nitro­benzyl­idene)hydrazin-1-yl]-2-oxoeth­yl}benzene­sulfonamide N,N-di­methyl­formamide monosolvate

Purandara, H.; Foro, S.; Thimme Gowda, B.

doi:10.1107/S2056989017014669

Crystal structure of (E)-4-methyl-N-{2-[2-(4-nitrobenzylidene)hydrazin-1-yl]-2-oxoethyl}benzenesulfonamide N,N-dimethylformamide monosolvate

H. Purandara, S. Foro and B. Thimme Gowda

The title Schiff base molecule displays a trans configurations with respect to the C=N double bond. Intermolecular N—H

O and C —H

O hydrogen bonds connect centrosymmetrically related molecules into dimers, forming rings of $R_{3}^{3}$ (11) and $R_{2}^{2}$ (10) graph-set motif stacked along the a axis into a columnar arrangement.

Keywords: crystal structure; Schiff base; conformation; C—H

O hydrogen bond.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989017014669/rz5222sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989017014669/rz5222Isup2.hkl Contains datablock I

CCDC reference: 1433602

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R factor = 0.039
wR factor = 0.108
Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT244_ALERT_4_C Low    'Solvent' Ueq as Compared to Neighbors of         N5 Check
PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) .          1 Check

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          4 Note
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX 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
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          2 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          4 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Info

   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
   9 ALERT level G = General information/check it is not something unexpected

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009), Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(E)-4-Methyl-N-{2-[2-(4-nitrobenzylidene)hydrazin-1-yl]-2-oxoethyl}benzenesulfonamide N,N-dimethylformamide monosolvate top

Crystal data top

C₁₆H₁₆N₄O₅S·C₃H₇NO	Z = 2
M_r = 449.48	F(000) = 472
Triclinic, P1	D_x = 1.402 Mg m⁻³
a = 8.3515 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.5778 (9) Å	Cell parameters from 3760 reflections
c = 13.673 (1) Å	θ = 2.6–27.8°
α = 107.609 (7)°	µ = 0.20 mm⁻¹
β = 98.954 (8)°	T = 293 K
γ = 106.505 (8)°	Prism, colourless
V = 1064.57 (18) Å³	0.40 × 0.40 × 0.22 mm

Data collection top

Oxford Diffraction Xcalibur single-crystal X-ray diffractometer with Sapphire CCD Detector	3592 reflections with I > 2σ(I)
Rotation method data acquisition using ω scans	R_int = 0.010
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	θ_max = 26.4°, θ_min = 2.6°
T_min = 0.925, T_max = 0.958	h = −10→10
7611 measured reflections	k = −9→13
4347 independent reflections	l = −17→12

Refinement top

Refinement on F²	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.108	w = 1/[σ²(F_o²) + (0.0546P)² + 0.3531P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.005
4347 reflections	Δρ_max = 0.32 e Å⁻³
289 parameters	Δρ_min = −0.37 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
C1	0.2529 (2)	0.80172 (17)	0.30177 (12)	0.0350 (3)
C2	0.3764 (2)	0.73865 (18)	0.28367 (13)	0.0395 (4)
H2	0.3431	0.6405	0.2546	0.047*
C3	0.5479 (2)	0.8222 (2)	0.30897 (14)	0.0436 (4)
H3	0.6298	0.7794	0.2971	0.052*
C4	0.6013 (2)	0.9691 (2)	0.35194 (14)	0.0479 (4)
C5	0.4745 (3)	1.0292 (2)	0.3654 (2)	0.0671 (6)
H5	0.5067	1.1274	0.3914	0.080*
C6	0.3022 (3)	0.9472 (2)	0.34106 (17)	0.0567 (5)
H6	0.2198	0.9898	0.3511	0.068*
C7	−0.0943 (2)	0.74344 (18)	0.10290 (13)	0.0385 (4)
H7A	−0.0028	0.8356	0.1359	0.046*
H7B	−0.1997	0.7535	0.1198	0.046*
C8	−0.1211 (2)	0.69253 (16)	−0.01586 (13)	0.0348 (3)
C9	−0.2478 (2)	0.96612 (17)	−0.05202 (13)	0.0356 (3)
H9	−0.2613	0.9393	−0.1250	0.043*
C10	−0.2839 (2)	1.09163 (16)	0.00553 (12)	0.0340 (3)
C11	−0.2613 (3)	1.13753 (19)	0.11526 (14)	0.0476 (4)
H11	−0.2174	1.0903	0.1539	0.057*
C12	−0.3032 (3)	1.2520 (2)	0.16685 (14)	0.0503 (5)
H12	−0.2892	1.2819	0.2400	0.060*
C13	−0.3662 (2)	1.32173 (17)	0.10891 (13)	0.0386 (4)
C14	−0.3851 (2)	1.28192 (18)	0.00117 (14)	0.0415 (4)
H14	−0.4242	1.3322	−0.0364	0.050*
C15	−0.3449 (2)	1.16557 (18)	−0.05016 (13)	0.0401 (4)
H15	−0.3590	1.1364	−0.1233	0.048*
C16	0.7899 (3)	1.0600 (3)	0.3827 (2)	0.0686 (6)
H16A	0.8405	1.0282	0.3258	0.103*
H16B	0.8491	1.0529	0.4458	0.103*
H16C	0.8002	1.1568	0.3961	0.103*
C17	0.2091 (3)	0.3550 (2)	0.33832 (16)	0.0609 (6)
H17	0.1971	0.4207	0.3081	0.073*
C18	0.2597 (4)	0.3016 (3)	0.49621 (18)	0.0765 (7)
H18A	0.3792	0.3327	0.5340	0.115*
H18B	0.2256	0.2072	0.4450	0.115*
H18C	0.1896	0.3022	0.5456	0.115*
C19	0.2526 (5)	0.5369 (3)	0.50861 (19)	0.0921 (10)
H19A	0.2398	0.5910	0.4647	0.138*
H19B	0.3644	0.5825	0.5590	0.138*
H19C	0.1641	0.5308	0.5460	0.138*
N1	−0.04825 (19)	0.64431 (15)	0.14518 (11)	0.0387 (3)
H1N	−0.016 (2)	0.5851 (18)	0.1079 (14)	0.046*
N2	−0.17143 (19)	0.77528 (14)	−0.06336 (11)	0.0385 (3)
H2N	−0.181 (2)	0.758 (2)	−0.1298 (12)	0.046*
N3	−0.19806 (17)	0.89339 (13)	−0.00295 (10)	0.0347 (3)
N4	−0.4191 (2)	1.43967 (16)	0.16299 (13)	0.0497 (4)
N5	0.2367 (2)	0.39543 (18)	0.44244 (12)	0.0535 (4)
O1	0.02638 (17)	0.57237 (14)	0.29491 (11)	0.0516 (3)
O2	−0.05327 (16)	0.78629 (15)	0.32153 (10)	0.0501 (3)
O3	−0.09848 (18)	0.58545 (13)	−0.06656 (10)	0.0496 (3)
O4	−0.4233 (3)	1.46197 (19)	0.25518 (13)	0.0808 (5)
O5	−0.4588 (2)	1.50928 (16)	0.11362 (13)	0.0681 (4)
O6	0.1980 (3)	0.23973 (17)	0.27815 (11)	0.0757 (5)
S1	0.03312 (5)	0.69598 (5)	0.27126 (3)	0.03706 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0402 (8)	0.0406 (9)	0.0286 (7)	0.0209 (7)	0.0080 (6)	0.0129 (6)
C2	0.0461 (9)	0.0387 (9)	0.0435 (9)	0.0246 (7)	0.0132 (7)	0.0187 (7)
C3	0.0430 (9)	0.0543 (11)	0.0461 (10)	0.0285 (8)	0.0133 (7)	0.0242 (8)
C4	0.0438 (10)	0.0525 (11)	0.0418 (9)	0.0167 (8)	0.0063 (7)	0.0125 (8)
C5	0.0575 (12)	0.0384 (10)	0.0833 (16)	0.0156 (9)	0.0118 (11)	−0.0032 (10)
C6	0.0489 (11)	0.0439 (10)	0.0701 (13)	0.0260 (9)	0.0140 (9)	0.0031 (9)
C7	0.0469 (9)	0.0381 (8)	0.0363 (8)	0.0223 (7)	0.0093 (7)	0.0155 (7)
C8	0.0335 (8)	0.0330 (8)	0.0363 (8)	0.0132 (6)	0.0063 (6)	0.0109 (7)
C9	0.0408 (8)	0.0348 (8)	0.0327 (8)	0.0136 (7)	0.0085 (6)	0.0146 (7)
C10	0.0348 (8)	0.0321 (8)	0.0361 (8)	0.0111 (6)	0.0076 (6)	0.0152 (7)
C11	0.0671 (12)	0.0460 (10)	0.0337 (9)	0.0289 (9)	0.0038 (8)	0.0161 (8)
C12	0.0694 (12)	0.0498 (11)	0.0303 (9)	0.0282 (9)	0.0057 (8)	0.0098 (8)
C13	0.0383 (8)	0.0332 (8)	0.0417 (9)	0.0137 (7)	0.0074 (7)	0.0104 (7)
C14	0.0469 (9)	0.0421 (9)	0.0454 (9)	0.0223 (8)	0.0120 (7)	0.0234 (8)
C15	0.0487 (9)	0.0440 (9)	0.0349 (8)	0.0205 (8)	0.0122 (7)	0.0197 (7)
C16	0.0492 (12)	0.0686 (14)	0.0714 (15)	0.0119 (10)	0.0067 (10)	0.0157 (12)
C17	0.0906 (16)	0.0637 (13)	0.0425 (10)	0.0440 (12)	0.0159 (10)	0.0236 (10)
C18	0.125 (2)	0.0649 (14)	0.0463 (12)	0.0357 (15)	0.0264 (13)	0.0263 (11)
C19	0.148 (3)	0.0744 (16)	0.0518 (14)	0.0653 (18)	0.0017 (15)	0.0082 (12)
N1	0.0462 (8)	0.0389 (8)	0.0369 (8)	0.0245 (6)	0.0084 (6)	0.0143 (6)
N2	0.0517 (8)	0.0368 (7)	0.0301 (7)	0.0211 (6)	0.0092 (6)	0.0120 (6)
N3	0.0391 (7)	0.0319 (7)	0.0340 (7)	0.0150 (6)	0.0077 (5)	0.0118 (6)
N4	0.0467 (9)	0.0446 (9)	0.0519 (10)	0.0204 (7)	0.0073 (7)	0.0085 (7)
N5	0.0735 (11)	0.0551 (9)	0.0376 (8)	0.0337 (9)	0.0124 (7)	0.0157 (7)
O1	0.0566 (8)	0.0575 (8)	0.0568 (8)	0.0243 (6)	0.0169 (6)	0.0377 (7)
O2	0.0494 (7)	0.0667 (8)	0.0454 (7)	0.0334 (6)	0.0216 (6)	0.0190 (6)
O3	0.0665 (8)	0.0425 (7)	0.0430 (7)	0.0318 (6)	0.0107 (6)	0.0099 (5)
O4	0.1144 (14)	0.0879 (12)	0.0502 (9)	0.0643 (11)	0.0239 (9)	0.0111 (8)
O5	0.0834 (11)	0.0599 (9)	0.0783 (10)	0.0475 (8)	0.0219 (8)	0.0277 (8)
O6	0.1306 (15)	0.0703 (10)	0.0394 (8)	0.0556 (10)	0.0250 (8)	0.0178 (7)
S1	0.0401 (2)	0.0458 (2)	0.0349 (2)	0.02253 (18)	0.01295 (16)	0.01948 (18)

Geometric parameters (Å, º) top

C1—C6	1.377 (2)	C13—C14	1.374 (2)
C1—C2	1.393 (2)	C13—N4	1.468 (2)
C1—S1	1.7629 (17)	C14—C15	1.381 (2)
C2—C3	1.376 (2)	C14—H14	0.9300
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.389 (3)	C16—H16A	0.9600
C3—H3	0.9300	C16—H16B	0.9600
C4—C5	1.390 (3)	C16—H16C	0.9600
C4—C16	1.507 (3)	C17—O6	1.215 (2)
C5—C6	1.379 (3)	C17—N5	1.318 (2)
C5—H5	0.9300	C17—H17	0.9300
C6—H6	0.9300	C18—N5	1.438 (3)
C7—N1	1.452 (2)	C18—H18A	0.9600
C7—C8	1.505 (2)	C18—H18B	0.9600
C7—H7A	0.9700	C18—H18C	0.9600
C7—H7B	0.9700	C19—N5	1.451 (3)
C8—O3	1.2191 (19)	C19—H19A	0.9600
C8—N2	1.354 (2)	C19—H19B	0.9600
C9—N3	1.274 (2)	C19—H19C	0.9600
C9—C10	1.464 (2)	N1—S1	1.6082 (14)
C9—H9	0.9300	N1—H1N	0.818 (15)
C10—C15	1.384 (2)	N2—N3	1.3723 (18)
C10—C11	1.393 (2)	N2—H2N	0.856 (15)
C11—C12	1.374 (3)	N4—O5	1.216 (2)
C11—H11	0.9300	N4—O4	1.218 (2)
C12—C13	1.376 (2)	O1—S1	1.4273 (13)
C12—H12	0.9300	O2—S1	1.4333 (13)

C6—C1—C2	119.83 (16)	C15—C14—H14	120.7
C6—C1—S1	119.93 (13)	C14—C15—C10	121.03 (16)
C2—C1—S1	120.22 (13)	C14—C15—H15	119.5
C3—C2—C1	119.72 (16)	C10—C15—H15	119.5
C3—C2—H2	120.1	C4—C16—H16A	109.5
C1—C2—H2	120.1	C4—C16—H16B	109.5
C2—C3—C4	121.40 (16)	H16A—C16—H16B	109.5
C2—C3—H3	119.3	C4—C16—H16C	109.5
C4—C3—H3	119.3	H16A—C16—H16C	109.5
C3—C4—C5	117.63 (18)	H16B—C16—H16C	109.5
C3—C4—C16	121.21 (18)	O6—C17—N5	126.0 (2)
C5—C4—C16	121.16 (19)	O6—C17—H17	117.0
C6—C5—C4	121.71 (18)	N5—C17—H17	117.0
C6—C5—H5	119.1	N5—C18—H18A	109.5
C4—C5—H5	119.1	N5—C18—H18B	109.5
C1—C6—C5	119.63 (17)	H18A—C18—H18B	109.5
C1—C6—H6	120.2	N5—C18—H18C	109.5
C5—C6—H6	120.2	H18A—C18—H18C	109.5
N1—C7—C8	110.67 (13)	H18B—C18—H18C	109.5
N1—C7—H7A	109.5	N5—C19—H19A	109.5
C8—C7—H7A	109.5	N5—C19—H19B	109.5
N1—C7—H7B	109.5	H19A—C19—H19B	109.5
C8—C7—H7B	109.5	N5—C19—H19C	109.5
H7A—C7—H7B	108.1	H19A—C19—H19C	109.5
O3—C8—N2	121.73 (15)	H19B—C19—H19C	109.5
O3—C8—C7	123.18 (14)	C7—N1—S1	118.51 (11)
N2—C8—C7	115.08 (13)	C7—N1—H1N	118.6 (14)
N3—C9—C10	120.54 (14)	S1—N1—H1N	115.5 (14)
N3—C9—H9	119.7	C8—N2—N3	119.45 (13)
C10—C9—H9	119.7	C8—N2—H2N	120.9 (13)
C15—C10—C11	118.91 (15)	N3—N2—H2N	119.5 (13)
C15—C10—C9	119.51 (14)	C9—N3—N2	116.76 (13)
C11—C10—C9	121.57 (14)	O5—N4—O4	123.01 (17)
C12—C11—C10	120.49 (16)	O5—N4—C13	118.74 (16)
C12—C11—H11	119.8	O4—N4—C13	118.25 (16)
C10—C11—H11	119.8	C17—N5—C18	120.84 (18)
C11—C12—C13	119.13 (16)	C17—N5—C19	122.27 (18)
C11—C12—H12	120.4	C18—N5—C19	116.84 (17)
C13—C12—H12	120.4	O1—S1—O2	119.85 (8)
C14—C13—C12	121.87 (16)	O1—S1—N1	107.10 (8)
C14—C13—N4	118.89 (15)	O2—S1—N1	106.47 (8)
C12—C13—N4	119.22 (16)	O1—S1—C1	107.68 (8)
C13—C14—C15	118.52 (15)	O2—S1—C1	107.05 (8)
C13—C14—H14	120.7	N1—S1—C1	108.25 (8)

C6—C1—C2—C3	2.5 (3)	C11—C10—C15—C14	−0.8 (3)
S1—C1—C2—C3	−179.22 (12)	C9—C10—C15—C14	178.07 (15)
C1—C2—C3—C4	−0.4 (3)	C8—C7—N1—S1	164.48 (11)
C2—C3—C4—C5	−2.1 (3)	O3—C8—N2—N3	178.85 (15)
C2—C3—C4—C16	178.09 (18)	C7—C8—N2—N3	−1.6 (2)
C3—C4—C5—C6	2.5 (3)	C10—C9—N3—N2	178.34 (13)
C16—C4—C5—C6	−177.7 (2)	C8—N2—N3—C9	−178.98 (14)
C2—C1—C6—C5	−2.1 (3)	C14—C13—N4—O5	−8.6 (3)
S1—C1—C6—C5	179.61 (17)	C12—C13—N4—O5	173.06 (18)
C4—C5—C6—C1	−0.4 (4)	C14—C13—N4—O4	170.45 (18)
N1—C7—C8—O3	−3.0 (2)	C12—C13—N4—O4	−7.9 (3)
N1—C7—C8—N2	177.44 (14)	O6—C17—N5—C18	1.0 (4)
N3—C9—C10—C15	−177.27 (15)	O6—C17—N5—C19	178.4 (3)
N3—C9—C10—C11	1.6 (2)	C7—N1—S1—O1	165.96 (13)
C15—C10—C11—C12	1.7 (3)	C7—N1—S1—O2	36.61 (15)
C9—C10—C11—C12	−177.14 (17)	C7—N1—S1—C1	−78.19 (14)
C10—C11—C12—C13	−0.7 (3)	C6—C1—S1—O1	−145.65 (15)
C11—C12—C13—C14	−1.3 (3)	C2—C1—S1—O1	36.03 (15)
C11—C12—C13—N4	177.02 (17)	C6—C1—S1—O2	−15.55 (17)
C12—C13—C14—C15	2.2 (3)	C2—C1—S1—O2	166.13 (13)
N4—C13—C14—C15	−176.14 (15)	C6—C1—S1—N1	98.87 (16)
C13—C14—C15—C10	−1.1 (3)	C2—C1—S1—N1	−79.45 (14)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3ⁱ	0.82 (2)	2.24 (2)	3.0142 (18)	158 (2)
N2—H2N···O6ⁱ	0.86 (2)	2.02 (2)	2.863 (2)	168 (2)
C3—H3···O2ⁱⁱ	0.93	2.59	3.442 (2)	152
C14—H14···O5ⁱⁱⁱ	0.93	2.56	3.484 (2)	171
C18—H18C···O2^iv	0.96	2.56	3.446 (3)	154
C15—H15···Cg1^v	0.93	2.66	3.564 (2)	164

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

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

Crystal structure of (E)-4-methyl-N-{2-[2-(4-nitro­benzyl­idene)hydrazin-1-yl]-2-oxoeth­yl}benzene­sulfonamide N,N-di­methyl­formamide monosolvate

Supporting information

Key indicators

checkCIF/PLATON results

Crystal structure of (E)-4-methyl-N-{2-[2-(4-nitrobenzylidene)hydrazin-1-yl]-2-oxoethyl}benzenesulfonamide N,N-dimethylformamide monosolvate