Crystal structure and Hirshfeld surface analysis of (E)-4-chloro-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/S205698901800292X

Crystal structure and Hirshfeld surface analysis of (E)-4-chloro-N-{2-[2-(4-nitrobenzylidene)hydrazin-1-yl]-2-oxoethyl}benzenesulfonamide N,N-dimethylformamide monosolvate

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

Reaction of N-(4-chlorobenzenesulfonyl)glycinyl hydrazide with 4-nitrobenzaldehyde gives the N,N-dimethylformamide monosolvated N-acylhydrazone derivative, (E)-N-{2-[2-(4-nitrobenzylidene)- hydrazine-1-yl]-2-oxoethyl}-4-χhlorobenzenesulfonamide. Rings of $R_{2}^{2}$ (10) and $R_{3}^{3}$ (11) graph-set motifs are formed in the crystal structure by N—H

O and C—H

O hydrogen bonds. The two-dimensional fingerprint (FP) plots for significant intermolecular interactions indicate that the greatest contribution is from the O

H/H

O contacts (31.3%), corresponding to N

O/C

O interactions.

Keywords: crystal structure; hydrazone; intermolecular hydrogen bonds; inversion dimers; Hirshfeld surface analysis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S205698901800292X/rz5227sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S205698901800292X/rz5227Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S205698901800292X/rz5227Isup3.cml Supplementary material

CCDC reference: 1433601

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.009 Å
R factor = 0.090
wR factor = 0.167
Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         C4 Check
PLAT244_ALERT_4_C Low    'Solvent' Ueq as Compared to Neighbors of         N5 Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............      0.009 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     20.655 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.455 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         50 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

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
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)       0.01 Degree
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....        C17 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          6 Note

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

   4 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
   6 ALERT type 3 Indicator that the structure quality may be low
   4 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: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008) and PLATON (Spek, 2015); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

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

Crystal data top

C₁₅H₁₃ClN₄O₅S·C₃H₇NO	Z = 2
M_r = 469.90	F(000) = 488
Triclinic, P1	D_x = 1.460 Mg m⁻³
a = 8.240 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.631 (1) Å	Cell parameters from 1907 reflections
c = 13.720 (2) Å	θ = 2.6–28.0°
α = 108.15 (1)°	µ = 0.32 mm⁻¹
β = 98.36 (1)°	T = 293 K
γ = 105.07 (1)°	Plate, yellow
V = 1068.7 (2) Å³	0.46 × 0.22 × 0.08 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2623 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	R_int = 0.027
Rotation method data acquisition using ω scans.	θ_max = 25.4°, θ_min = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→8
T_min = 0.866, T_max = 0.975	k = −12→12
6809 measured reflections	l = −14→16
3847 independent reflections

Refinement top

Refinement on F²	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.090	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.167	w = 1/[σ²(F_o²) + 3.0287P] where P = (F_o² + 2F_c²)/3
S = 1.32	(Δ/σ)_max < 0.001
3847 reflections	Δρ_max = 0.61 e Å⁻³
288 parameters	Δρ_min = −0.43 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
Cl1	1.2884 (2)	1.0818 (2)	0.38232 (19)	0.0962 (7)
S1	0.52061 (19)	0.69212 (16)	0.26923 (12)	0.0430 (4)
O1	0.5214 (5)	0.5704 (4)	0.2924 (3)	0.0570 (11)
O2	0.4256 (5)	0.7784 (4)	0.3183 (3)	0.0554 (11)
O3	0.3990 (5)	0.5834 (4)	−0.0674 (3)	0.0561 (11)
O4	0.0376 (6)	1.5139 (5)	0.1175 (4)	0.0744 (14)
O5	0.0718 (7)	1.4667 (5)	0.2589 (4)	0.0824 (16)
N1	0.4475 (6)	0.6423 (5)	0.1438 (4)	0.0429 (11)
H1N	0.482 (7)	0.581 (4)	0.103 (4)	0.051*
N2	0.3264 (6)	0.7745 (5)	−0.0636 (4)	0.0420 (11)
H2N	0.321 (7)	0.760 (6)	−0.1298 (19)	0.050*
N3	0.2997 (5)	0.8933 (4)	−0.0024 (3)	0.0364 (10)
N4	0.0771 (6)	1.4444 (5)	0.1669 (5)	0.0534 (13)
C1	0.7391 (7)	0.8014 (6)	0.3018 (4)	0.0406 (13)
C2	0.7777 (9)	0.9455 (7)	0.3399 (6)	0.069 (2)
H2	0.6897	0.9846	0.3496	0.083*
C3	0.9470 (9)	1.0308 (7)	0.3635 (6)	0.077 (2)
H3	0.9738	1.1275	0.3882	0.092*
C4	1.0758 (8)	0.9717 (7)	0.3501 (5)	0.0572 (17)
C5	1.0392 (8)	0.8290 (7)	0.3112 (5)	0.0495 (15)
H5	1.1276	0.7904	0.3015	0.059*
C6	0.8695 (8)	0.7438 (6)	0.2866 (5)	0.0467 (15)
H6	0.8429	0.6470	0.2598	0.056*
C7	0.4001 (7)	0.7410 (6)	0.1009 (4)	0.0421 (13)
H7A	0.4905	0.8313	0.1332	0.051*
H7B	0.2936	0.7527	0.1181	0.051*
C8	0.3754 (7)	0.6906 (5)	−0.0167 (4)	0.0386 (13)
C9	0.2531 (7)	0.9679 (5)	−0.0504 (4)	0.0383 (13)
H9	0.2425	0.9424	−0.1229	0.046*
C10	0.2161 (6)	1.0935 (5)	0.0081 (4)	0.0355 (12)
C11	0.2339 (8)	1.1382 (6)	0.1170 (4)	0.0483 (15)
H11	0.2757	1.0895	0.1548	0.058*
C12	0.1910 (8)	1.2531 (6)	0.1696 (5)	0.0506 (15)
H12	0.2019	1.2819	0.2422	0.061*
C13	0.1312 (7)	1.3247 (6)	0.1119 (4)	0.0408 (13)
C14	0.1167 (7)	1.2873 (6)	0.0058 (5)	0.0467 (14)
H14	0.0795	1.3390	−0.0309	0.056*
C15	0.1584 (7)	1.1714 (6)	−0.0455 (5)	0.0450 (14)
H15	0.1479	1.1442	−0.1180	0.054*
O6	0.7001 (7)	0.2440 (5)	0.2779 (4)	0.0807 (16)
N5	0.7345 (7)	0.4007 (5)	0.4406 (4)	0.0602 (14)
C16	0.7123 (10)	0.3594 (8)	0.3368 (6)	0.069 (2)
H16A	0.7055	0.4252	0.3062	0.083*
C17	0.7557 (13)	0.5436 (8)	0.5057 (6)	0.104 (3)
H17A	0.7493	0.5976	0.4616	0.156*
H17B	0.8665	0.5839	0.5560	0.156*
H17C	0.6654	0.5439	0.5427	0.156*
C18	0.7419 (12)	0.3051 (8)	0.4940 (6)	0.091 (3)
H18A	0.7043	0.2114	0.4429	0.136*
H18B	0.6675	0.3117	0.5418	0.136*
H18C	0.8589	0.3282	0.5330	0.136*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0548 (12)	0.0931 (16)	0.1126 (18)	0.0029 (11)	0.0042 (11)	0.0249 (13)
S1	0.0452 (8)	0.0514 (9)	0.0430 (8)	0.0233 (7)	0.0149 (7)	0.0232 (7)
O1	0.061 (3)	0.061 (3)	0.063 (3)	0.023 (2)	0.017 (2)	0.038 (2)
O2	0.053 (3)	0.072 (3)	0.056 (3)	0.037 (2)	0.025 (2)	0.023 (2)
O3	0.074 (3)	0.047 (3)	0.050 (3)	0.034 (2)	0.013 (2)	0.010 (2)
O4	0.090 (4)	0.059 (3)	0.090 (4)	0.048 (3)	0.021 (3)	0.030 (3)
O5	0.109 (4)	0.080 (4)	0.063 (3)	0.055 (3)	0.026 (3)	0.010 (3)
N1	0.052 (3)	0.040 (3)	0.043 (3)	0.027 (2)	0.009 (2)	0.015 (2)
N2	0.057 (3)	0.038 (3)	0.036 (3)	0.026 (2)	0.011 (2)	0.014 (2)
N3	0.040 (3)	0.031 (2)	0.039 (3)	0.014 (2)	0.009 (2)	0.010 (2)
N4	0.048 (3)	0.045 (3)	0.061 (4)	0.020 (3)	0.011 (3)	0.008 (3)
C1	0.044 (3)	0.049 (3)	0.036 (3)	0.024 (3)	0.012 (3)	0.018 (3)
C2	0.060 (4)	0.052 (4)	0.085 (5)	0.031 (4)	0.017 (4)	0.001 (4)
C3	0.054 (4)	0.041 (4)	0.105 (6)	0.009 (3)	0.014 (4)	−0.005 (4)
C4	0.044 (4)	0.062 (4)	0.048 (4)	0.007 (3)	0.003 (3)	0.009 (3)
C5	0.045 (4)	0.062 (4)	0.054 (4)	0.029 (3)	0.018 (3)	0.027 (3)
C6	0.057 (4)	0.048 (4)	0.053 (4)	0.030 (3)	0.021 (3)	0.027 (3)
C7	0.047 (3)	0.043 (3)	0.041 (3)	0.022 (3)	0.012 (3)	0.016 (3)
C8	0.034 (3)	0.034 (3)	0.040 (3)	0.010 (2)	0.003 (2)	0.007 (3)
C9	0.043 (3)	0.038 (3)	0.035 (3)	0.014 (3)	0.010 (2)	0.015 (3)
C10	0.032 (3)	0.034 (3)	0.042 (3)	0.009 (2)	0.008 (2)	0.016 (2)
C11	0.065 (4)	0.048 (4)	0.038 (3)	0.027 (3)	0.007 (3)	0.019 (3)
C12	0.065 (4)	0.048 (4)	0.035 (3)	0.022 (3)	0.005 (3)	0.010 (3)
C13	0.039 (3)	0.037 (3)	0.039 (3)	0.011 (3)	0.004 (3)	0.008 (3)
C14	0.050 (4)	0.040 (3)	0.061 (4)	0.020 (3)	0.015 (3)	0.027 (3)
C15	0.051 (4)	0.049 (4)	0.045 (3)	0.023 (3)	0.013 (3)	0.025 (3)
O6	0.135 (5)	0.075 (3)	0.045 (3)	0.056 (3)	0.028 (3)	0.017 (3)
N5	0.085 (4)	0.057 (3)	0.042 (3)	0.034 (3)	0.014 (3)	0.014 (3)
C16	0.100 (6)	0.075 (5)	0.052 (5)	0.051 (5)	0.022 (4)	0.030 (4)
C17	0.165 (9)	0.083 (6)	0.064 (5)	0.072 (6)	0.004 (5)	0.010 (5)
C18	0.145 (8)	0.077 (5)	0.056 (5)	0.032 (5)	0.034 (5)	0.030 (4)

Geometric parameters (Å, º) top

Cl1—C4	1.739 (6)	C7—H7A	0.9700
S1—O1	1.427 (4)	C7—H7B	0.9700
S1—O2	1.431 (4)	C9—C10	1.461 (7)
S1—N1	1.603 (5)	C9—H9	0.9300
S1—C1	1.773 (6)	C10—C15	1.390 (7)
O3—C8	1.217 (6)	C10—C11	1.392 (7)
O4—N4	1.217 (6)	C11—C12	1.374 (8)
O5—N4	1.221 (6)	C11—H11	0.9300
N1—C7	1.460 (6)	C12—C13	1.380 (7)
N1—H1N	0.854 (19)	C12—H12	0.9300
N2—C8	1.357 (7)	C13—C14	1.362 (8)
N2—N3	1.374 (6)	C14—C15	1.372 (7)
N2—H2N	0.865 (19)	C14—H14	0.9300
N3—C9	1.274 (6)	C15—H15	0.9300
N4—C13	1.477 (7)	O6—C16	1.210 (8)
C1—C6	1.379 (7)	N5—C16	1.322 (8)
C1—C2	1.386 (8)	N5—C18	1.434 (8)
C2—C3	1.379 (9)	N5—C17	1.452 (8)
C2—H2	0.9300	C16—H16A	0.9300
C3—C4	1.373 (9)	C17—H17A	0.9600
C3—H3	0.9300	C17—H17B	0.9600
C4—C5	1.375 (8)	C17—H17C	0.9600
C5—C6	1.380 (8)	C18—H18A	0.9600
C5—H5	0.9300	C18—H18B	0.9600
C6—H6	0.9300	C18—H18C	0.9600
C7—C8	1.496 (7)

O1—S1—O2	120.2 (3)	O3—C8—C7	123.2 (5)
O1—S1—N1	107.3 (2)	N2—C8—C7	115.1 (5)
O2—S1—N1	107.0 (2)	N3—C9—C10	120.2 (5)
O1—S1—C1	107.6 (3)	N3—C9—H9	119.9
O2—S1—C1	106.8 (3)	C10—C9—H9	119.9
N1—S1—C1	107.4 (3)	C15—C10—C11	117.8 (5)
C7—N1—S1	118.6 (4)	C15—C10—C9	119.9 (5)
C7—N1—H1N	116 (4)	C11—C10—C9	122.2 (5)
S1—N1—H1N	118 (4)	C12—C11—C10	121.2 (5)
C8—N2—N3	119.1 (4)	C12—C11—H11	119.4
C8—N2—H2N	122 (4)	C10—C11—H11	119.4
N3—N2—H2N	118 (4)	C11—C12—C13	118.4 (5)
C9—N3—N2	116.6 (4)	C11—C12—H12	120.8
O4—N4—O5	123.6 (5)	C13—C12—H12	120.8
O4—N4—C13	118.4 (6)	C14—C13—C12	122.5 (5)
O5—N4—C13	118.0 (5)	C14—C13—N4	118.7 (5)
C6—C1—C2	120.0 (6)	C12—C13—N4	118.8 (5)
C6—C1—S1	120.4 (4)	C13—C14—C15	118.3 (5)
C2—C1—S1	119.6 (4)	C13—C14—H14	120.9
C3—C2—C1	119.7 (6)	C15—C14—H14	120.9
C3—C2—H2	120.1	C14—C15—C10	121.8 (5)
C1—C2—H2	120.1	C14—C15—H15	119.1
C4—C3—C2	119.5 (6)	C10—C15—H15	119.1
C4—C3—H3	120.2	C16—N5—C18	120.7 (6)
C2—C3—H3	120.2	C16—N5—C17	122.2 (6)
C3—C4—C5	121.4 (6)	C18—N5—C17	117.1 (6)
C3—C4—Cl1	118.5 (5)	O6—C16—N5	126.0 (7)
C5—C4—Cl1	120.1 (5)	O6—C16—H16A	117.0
C4—C5—C6	119.0 (5)	N5—C16—H16A	117.0
C4—C5—H5	120.5	N5—C17—H17A	109.5
C6—C5—H5	120.5	N5—C17—H17B	109.5
C1—C6—C5	120.3 (6)	H17A—C17—H17B	109.5
C1—C6—H6	119.8	N5—C17—H17C	109.5
C5—C6—H6	119.8	H17A—C17—H17C	109.5
N1—C7—C8	111.2 (4)	H17B—C17—H17C	109.5
N1—C7—H7A	109.4	N5—C18—H18A	109.5
C8—C7—H7A	109.4	N5—C18—H18B	109.5
N1—C7—H7B	109.4	H18A—C18—H18B	109.5
C8—C7—H7B	109.4	N5—C18—H18C	109.5
H7A—C7—H7B	108.0	H18A—C18—H18C	109.5
O3—C8—N2	121.7 (5)	H18B—C18—H18C	109.5

O1—S1—N1—C7	167.8 (4)	N3—N2—C8—C7	−1.6 (7)
O2—S1—N1—C7	37.6 (5)	N1—C7—C8—O3	−2.5 (8)
C1—S1—N1—C7	−76.7 (5)	N1—C7—C8—N2	178.3 (5)
C8—N2—N3—C9	−179.7 (5)	N2—N3—C9—C10	177.9 (4)
O1—S1—C1—C6	35.0 (5)	N3—C9—C10—C15	−177.4 (5)
O2—S1—C1—C6	165.3 (4)	N3—C9—C10—C11	1.6 (8)
N1—S1—C1—C6	−80.2 (5)	C15—C10—C11—C12	2.0 (9)
O1—S1—C1—C2	−146.7 (5)	C9—C10—C11—C12	−177.1 (5)
O2—S1—C1—C2	−16.4 (6)	C10—C11—C12—C13	−0.7 (9)
N1—S1—C1—C2	98.1 (5)	C11—C12—C13—C14	−1.3 (9)
C6—C1—C2—C3	−0.6 (10)	C11—C12—C13—N4	177.2 (5)
S1—C1—C2—C3	−178.8 (6)	O4—N4—C13—C14	−7.1 (8)
C1—C2—C3—C4	−0.8 (12)	O5—N4—C13—C14	171.7 (6)
C2—C3—C4—C5	1.6 (12)	O4—N4—C13—C12	174.3 (6)
C2—C3—C4—Cl1	−179.1 (6)	O5—N4—C13—C12	−7.0 (8)
C3—C4—C5—C6	−1.0 (10)	C12—C13—C14—C15	2.0 (9)
Cl1—C4—C5—C6	179.7 (5)	N4—C13—C14—C15	−176.6 (5)
C2—C1—C6—C5	1.2 (9)	C13—C14—C15—C10	−0.7 (8)
S1—C1—C6—C5	179.5 (4)	C11—C10—C15—C14	−1.3 (8)
C4—C5—C6—C1	−0.5 (9)	C9—C10—C15—C14	177.8 (5)
S1—N1—C7—C8	166.5 (4)	C18—N5—C16—O6	−1.6 (12)
N3—N2—C8—O3	179.2 (5)	C17—N5—C16—O6	177.1 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3ⁱ	0.85 (2)	2.18 (3)	2.976 (6)	155 (5)
N2—H2N···O6ⁱ	0.87 (2)	2.00 (2)	2.857 (6)	171 (5)
C5—H5···O2ⁱⁱ	0.93	2.47	3.357 (7)	159
C14—H14···O4ⁱⁱⁱ	0.93	2.53	3.457 (7)	175
C16—H16A···O1	0.93	2.46	3.207 (8)	138
C18—H18B···O2^iv	0.96	2.53	3.339 (8)	142
C15—H15···Cg1^v	0.93	2.72	3.629 (7)	167

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

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Crystal structure and Hirshfeld surface analysis of (E)-4-chloro-N-{2-[2-(4-nitro­benzyl­idene)hydrazin-1-yl]-2-oxoeth­yl}benzene­sulfonamide N,N-di­methyl­formamide monosolvate

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Crystal structure and Hirshfeld surface analysis of (E)-4-chloro-N-{2-[2-(4-nitrobenzylidene)hydrazin-1-yl]-2-oxoethyl}benzenesulfonamide N,N-dimethylformamide monosolvate