Crystal structures of three ortho-substituted N-acyl­hydrazone derivatives

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

doi:10.1107/S2056989017016814

Crystal structures of three ortho-substituted N-acylhydrazone derivatives

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

The effect of the nature of substitutions on the structural parameters and hydrogen-bonding interactions in N-acylhydrazone derivatives has been studied by synthesizing and determining the crystal structures of three ortho-substituted N-acylhydrazone derivatives, namely (E)-N-{2-[2-(2-chlorobenzylidene)hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide (I), (E)-N-{2-[2-(2-methylbenzylidene)hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide (II) and (E)-N-{2-[2-(2-nitrobenzylidene)hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide (III).

Keywords: crystal structure; N-acylhydrazones; ring motifs; conformation; C—H

O interaction.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989017016814/rz5225sup1.cif Contains datablocks I, II, III
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989017016814/rz5225Isup2.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989017016814/rz5225IIsup3.hkl Contains datablock II
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989017016814/rz5225IIIsup4.hkl Contains datablock III
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989017016814/rz5225Isup5.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989017016814/rz5225IIsup6.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989017016814/rz5225IIIsup7.cml Supplementary material

CCDC references: 1433561; 1433612; 1433603

checkCIF report

Key indicators

Structure: I

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R factor = 0.062
wR factor = 0.131
Data-to-parameter ratio = 15.4

Structure: II

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.053
wR factor = 0.141
Data-to-parameter ratio = 13.8

Structure: III

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R factor = 0.057
wR factor = 0.131
Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT220_ALERT_2_C Non-Solvent Resd 1  C   Ueq(max)/Ueq(min) Range         3.5 Ratio
PLAT222_ALERT_3_C Non-Solv.  Resd 1  H   Uiso(max)/Uiso(min) Range        4.1 Ratio
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         C4 Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0056 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      8.893 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         18 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          4 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          1 Report
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          1 Report
PLAT186_ALERT_4_G The CIF-Embedded .res File Contains ISOR 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 .............          8 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         21 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

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

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




Datablock: II


Alert level C
PLAT018_ALERT_1_C _diffrn_measured_fraction_theta_max .NE. *_full           ! Check
PLAT220_ALERT_2_C Non-Solvent Resd 1  C   Ueq(max)/Ueq(min) Range         3.3 Ratio
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0055 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      6.796 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.599         25 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
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          1 Report
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          1 Report
PLAT186_ALERT_4_G The CIF-Embedded .res File Contains ISOR 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 .............          8 Note
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        39% Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note

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

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




Datablock: III



Alert level C
PLAT220_ALERT_2_C Non-Solvent Resd 1  C   Ueq(max)/Ueq(min) Range         3.1 Ratio
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         N4 Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00467 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      5.126 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          7 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          3 Report
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          1 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          1 Report
PLAT177_ALERT_4_G The CIF-Embedded .res File Contains DELU Records          1 Report
PLAT186_ALERT_4_G The CIF-Embedded .res File Contains ISOR 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  )         4% Note
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         10 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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

For all structures, 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: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

(E)-N-{2-[2-(2-Chlorobenzylidene)hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide (I) top

Crystal data top

C₁₆H₁₆ClN₃O₃S	Z = 2
M_r = 365.83	F(000) = 380
Triclinic, P1	D_x = 1.422 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.867 (1) Å	Cell parameters from 2213 reflections
b = 10.340 (1) Å	θ = 2.7–27.8°
c = 10.997 (2) Å	µ = 0.37 mm⁻¹
α = 84.96 (1)°	T = 293 K
β = 75.46 (1)°	Plate, colourless
γ = 81.13 (1)°	0.50 × 0.36 × 0.18 mm
V = 854.4 (2) Å³

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2709 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	R_int = 0.021
Rotation method data acquisition using ω scans	θ_max = 26.4°, θ_min = 2.7°
Absorption correction: multi-scan CrysAlis RED (Oxford Diffraction, 2009)	h = −9→9
T_min = 0.838, T_max = 0.937	k = −12→12
5855 measured reflections	l = −13→13
3444 independent reflections

Refinement top

Refinement on F²	8 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.062	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.131	w = 1/[σ²(F_o²) + (0.0196P)² + 0.9514P] where P = (F_o² + 2F_c²)/3
S = 1.29	(Δ/σ)_max = 0.001
3444 reflections	Δρ_max = 0.26 e Å⁻³
224 parameters	Δρ_min = −0.28 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	0.1690 (4)	0.5986 (3)	0.3391 (3)	0.0455 (8)
C2	0.0073 (5)	0.5621 (4)	0.3404 (3)	0.0553 (9)
H2	0.0019	0.4856	0.3039	0.066*
C3	−0.1476 (5)	0.6406 (5)	0.3968 (4)	0.0728 (13)
H3	−0.2567	0.6152	0.3986	0.087*
C4	−0.1428 (6)	0.7543 (5)	0.4497 (4)	0.0762 (13)
C5	0.0198 (7)	0.7875 (4)	0.4496 (4)	0.0803 (14)
H5	0.0250	0.8637	0.4867	0.096*
C6	0.1762 (6)	0.7103 (4)	0.3955 (4)	0.0655 (11)
H6	0.2849	0.7338	0.3974	0.079*
C7	0.5616 (4)	0.6710 (3)	0.1041 (4)	0.0472 (8)
H7A	0.5499	0.7162	0.1800	0.057*
H7B	0.5426	0.7365	0.0384	0.057*
C8	0.7477 (4)	0.5978 (3)	0.0656 (3)	0.0363 (7)
C9	0.9704 (4)	0.8454 (3)	0.1176 (3)	0.0384 (7)
H9	1.0861	0.8028	0.0963	0.046*
C10	0.9332 (4)	0.9799 (3)	0.1602 (3)	0.0376 (7)
C11	1.0632 (4)	1.0477 (3)	0.1782 (3)	0.0416 (7)
C12	1.0240 (5)	1.1749 (3)	0.2181 (4)	0.0541 (9)
H12	1.1130	1.2182	0.2307	0.065*
C13	0.8524 (5)	1.2361 (3)	0.2387 (4)	0.0595 (10)
H13	0.8251	1.3213	0.2655	0.071*
C14	0.7207 (5)	1.1729 (3)	0.2202 (4)	0.0588 (10)
H14	0.6049	1.2154	0.2336	0.071*
C15	0.7608 (4)	1.0463 (3)	0.1817 (3)	0.0483 (8)
H15	0.6706	1.0040	0.1698	0.058*
C16	−0.3116 (7)	0.8436 (6)	0.5055 (5)	0.126 (2)
H16A	−0.4108	0.7957	0.5215	0.188*
H16B	−0.3280	0.9166	0.4473	0.188*
H16C	−0.3026	0.8751	0.5829	0.188*
N1	0.4270 (4)	0.5847 (3)	0.1266 (3)	0.0500 (7)
H1N	0.381 (5)	0.572 (4)	0.068 (3)	0.060*
N2	0.8803 (3)	0.6631 (2)	0.0693 (3)	0.0388 (6)
H2N	0.987 (3)	0.625 (3)	0.044 (3)	0.047*
N3	0.8414 (3)	0.7884 (2)	0.1104 (2)	0.0386 (6)
O1	0.3203 (3)	0.3846 (2)	0.2318 (3)	0.0677 (8)
O2	0.4985 (3)	0.5068 (3)	0.3261 (3)	0.0708 (8)
O3	0.7779 (3)	0.4849 (2)	0.0302 (2)	0.0445 (6)
Cl1	1.28438 (12)	0.97633 (10)	0.14816 (11)	0.0677 (3)
S1	0.36582 (11)	0.50602 (8)	0.25882 (9)	0.0486 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0432 (18)	0.0427 (18)	0.0470 (19)	−0.0067 (14)	−0.0047 (15)	−0.0005 (15)
C2	0.047 (2)	0.061 (2)	0.058 (2)	−0.0089 (17)	−0.0117 (17)	0.0025 (18)
C3	0.041 (2)	0.107 (4)	0.059 (3)	−0.002 (2)	−0.0046 (18)	0.015 (3)
C4	0.070 (3)	0.084 (3)	0.052 (2)	0.018 (2)	0.006 (2)	0.012 (2)
C5	0.101 (4)	0.060 (3)	0.063 (3)	0.001 (2)	0.008 (3)	−0.018 (2)
C6	0.065 (2)	0.063 (3)	0.065 (3)	−0.013 (2)	−0.001 (2)	−0.017 (2)
C7	0.0312 (16)	0.0410 (18)	0.067 (2)	−0.0049 (13)	−0.0036 (15)	−0.0137 (16)
C8	0.0335 (15)	0.0321 (16)	0.0429 (17)	−0.0045 (12)	−0.0077 (13)	−0.0036 (13)
C9	0.0335 (15)	0.0310 (15)	0.0487 (19)	−0.0035 (12)	−0.0062 (14)	−0.0036 (14)
C10	0.0371 (16)	0.0293 (15)	0.0456 (18)	−0.0065 (12)	−0.0080 (14)	−0.0005 (13)
C11	0.0409 (17)	0.0337 (16)	0.0515 (19)	−0.0070 (13)	−0.0125 (14)	−0.0014 (14)
C12	0.067 (2)	0.0386 (19)	0.063 (2)	−0.0193 (17)	−0.0191 (19)	−0.0059 (17)
C13	0.071 (3)	0.0337 (18)	0.073 (3)	−0.0028 (17)	−0.015 (2)	−0.0138 (18)
C14	0.052 (2)	0.041 (2)	0.076 (3)	0.0058 (16)	−0.0056 (19)	−0.0110 (18)
C15	0.0385 (17)	0.0392 (18)	0.066 (2)	−0.0064 (14)	−0.0073 (16)	−0.0083 (16)
C16	0.101 (4)	0.134 (5)	0.090 (4)	0.060 (4)	0.022 (3)	0.008 (3)
N1	0.0338 (14)	0.0640 (19)	0.0539 (18)	−0.0144 (13)	−0.0039 (13)	−0.0180 (15)
N2	0.0297 (13)	0.0296 (13)	0.0553 (17)	−0.0004 (10)	−0.0059 (12)	−0.0115 (12)
N3	0.0374 (14)	0.0272 (13)	0.0499 (16)	−0.0041 (10)	−0.0069 (12)	−0.0058 (11)
O1	0.0643 (17)	0.0380 (13)	0.100 (2)	−0.0060 (12)	−0.0151 (15)	−0.0128 (14)
O2	0.0538 (16)	0.083 (2)	0.081 (2)	0.0014 (14)	−0.0306 (14)	−0.0075 (16)
O3	0.0352 (11)	0.0325 (12)	0.0662 (15)	−0.0013 (9)	−0.0107 (10)	−0.0148 (11)
Cl1	0.0408 (5)	0.0574 (6)	0.1094 (9)	−0.0058 (4)	−0.0234 (5)	−0.0156 (5)
S1	0.0380 (4)	0.0432 (5)	0.0646 (6)	−0.0030 (3)	−0.0122 (4)	−0.0084 (4)

Geometric parameters (Å, º) top

C1—C6	1.373 (5)	C10—C11	1.387 (4)
C1—C2	1.378 (5)	C10—C15	1.396 (4)
C1—S1	1.760 (3)	C11—C12	1.388 (4)
C2—C3	1.390 (5)	C11—Cl1	1.744 (3)
C2—H2	0.9300	C12—C13	1.372 (5)
C3—C4	1.366 (7)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.370 (5)
C4—C5	1.375 (7)	C13—H13	0.9300
C4—C16	1.518 (6)	C14—C15	1.377 (5)
C5—C6	1.385 (6)	C14—H14	0.9300
C5—H5	0.9300	C15—H15	0.9300
C6—H6	0.9300	C16—H16A	0.9600
C7—N1	1.449 (4)	C16—H16B	0.9600
C7—C8	1.517 (4)	C16—H16C	0.9600
C7—H7A	0.9700	N1—S1	1.603 (3)
C7—H7B	0.9700	N1—H1N	0.843 (18)
C8—O3	1.232 (3)	N2—N3	1.374 (3)
C8—N2	1.338 (4)	N2—H2N	0.863 (18)
C9—N3	1.272 (4)	O1—S1	1.432 (3)
C9—C10	1.469 (4)	O2—S1	1.424 (3)
C9—H9	0.9300

C6—C1—C2	120.0 (3)	C10—C11—Cl1	120.7 (2)
C6—C1—S1	120.1 (3)	C12—C11—Cl1	117.4 (3)
C2—C1—S1	119.9 (3)	C13—C12—C11	119.1 (3)
C1—C2—C3	119.5 (4)	C13—C12—H12	120.4
C1—C2—H2	120.3	C11—C12—H12	120.4
C3—C2—H2	120.3	C14—C13—C12	120.7 (3)
C4—C3—C2	121.3 (4)	C14—C13—H13	119.6
C4—C3—H3	119.4	C12—C13—H13	119.6
C2—C3—H3	119.4	C13—C14—C15	119.7 (3)
C3—C4—C5	118.3 (4)	C13—C14—H14	120.2
C3—C4—C16	121.4 (5)	C15—C14—H14	120.2
C5—C4—C16	120.3 (5)	C14—C15—C10	121.7 (3)
C4—C5—C6	121.6 (4)	C14—C15—H15	119.2
C4—C5—H5	119.2	C10—C15—H15	119.2
C6—C5—H5	119.2	C4—C16—H16A	109.5
C1—C6—C5	119.3 (4)	C4—C16—H16B	109.5
C1—C6—H6	120.4	H16A—C16—H16B	109.5
C5—C6—H6	120.4	C4—C16—H16C	109.5
N1—C7—C8	112.3 (3)	H16A—C16—H16C	109.5
N1—C7—H7A	109.1	H16B—C16—H16C	109.5
C8—C7—H7A	109.1	C7—N1—S1	122.4 (3)
N1—C7—H7B	109.1	C7—N1—H1N	120 (3)
C8—C7—H7B	109.1	S1—N1—H1N	118 (3)
H7A—C7—H7B	107.9	C8—N2—N3	119.2 (2)
O3—C8—N2	120.9 (3)	C8—N2—H2N	118 (2)
O3—C8—C7	122.6 (3)	N3—N2—H2N	123 (2)
N2—C8—C7	116.5 (3)	C9—N3—N2	117.4 (2)
N3—C9—C10	118.7 (3)	O2—S1—O1	120.41 (17)
N3—C9—H9	120.6	O2—S1—N1	107.22 (16)
C10—C9—H9	120.6	O1—S1—N1	106.85 (17)
C11—C10—C15	116.9 (3)	O2—S1—C1	108.52 (17)
C11—C10—C9	123.2 (3)	O1—S1—C1	107.29 (16)
C15—C10—C9	119.9 (3)	N1—S1—C1	105.64 (16)
C10—C11—C12	121.9 (3)

C6—C1—C2—C3	1.4 (6)	C11—C12—C13—C14	0.0 (6)
S1—C1—C2—C3	−175.7 (3)	C12—C13—C14—C15	0.6 (6)
C1—C2—C3—C4	0.8 (6)	C13—C14—C15—C10	−0.3 (6)
C2—C3—C4—C5	−2.1 (6)	C11—C10—C15—C14	−0.6 (5)
C2—C3—C4—C16	176.9 (4)	C9—C10—C15—C14	−179.2 (3)
C3—C4—C5—C6	1.3 (7)	C8—C7—N1—S1	84.5 (3)
C16—C4—C5—C6	−177.7 (4)	O3—C8—N2—N3	−179.4 (3)
C2—C1—C6—C5	−2.2 (6)	C7—C8—N2—N3	2.0 (4)
S1—C1—C6—C5	174.9 (3)	C10—C9—N3—N2	179.5 (3)
C4—C5—C6—C1	0.9 (7)	C8—N2—N3—C9	177.1 (3)
N1—C7—C8—O3	15.4 (5)	C7—N1—S1—O2	−17.0 (3)
N1—C7—C8—N2	−166.0 (3)	C7—N1—S1—O1	−147.3 (3)
N3—C9—C10—C11	176.2 (3)	C7—N1—S1—C1	98.6 (3)
N3—C9—C10—C15	−5.3 (5)	C6—C1—S1—O2	37.5 (4)
C15—C10—C11—C12	1.2 (5)	C2—C1—S1—O2	−145.4 (3)
C9—C10—C11—C12	179.8 (3)	C6—C1—S1—O1	169.0 (3)
C15—C10—C11—Cl1	−177.5 (3)	C2—C1—S1—O1	−13.8 (3)
C9—C10—C11—Cl1	1.1 (5)	C6—C1—S1—N1	−77.2 (3)
C10—C11—C12—C13	−0.9 (5)	C2—C1—S1—N1	99.9 (3)
Cl1—C11—C12—C13	177.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3ⁱ	0.84 (2)	2.02 (2)	2.839 (3)	162 (4)
N2—H2N···O3ⁱⁱ	0.86 (2)	2.03 (2)	2.884 (3)	171 (3)
C12—H12···O1ⁱⁱⁱ	0.93	2.55	3.457 (4)	165

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

(E)-N-{2-[2-(2-Methylbenzylidene)hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide (II) top

Crystal data top

C₁₇H₁₉N₃O₃S	Z = 2
M_r = 345.41	F(000) = 364
Triclinic, P1	D_x = 1.319 Mg m⁻³
a = 7.984 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.320 (2) Å	Cell parameters from 2050 reflections
c = 11.081 (2) Å	θ = 2.7–27.9°
α = 85.17 (1)°	µ = 0.21 mm⁻¹
β = 74.89 (1)°	T = 293 K
γ = 81.14 (1)°	Prism, colourless
V = 870.0 (3) Å³	0.30 × 0.16 × 0.12 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2019 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 = 25.2°, θ_min = 2.7°
Absorption correction: multi-scan CrysAlis RED (Oxford Diffraction, 2009)	h = −5→9
T_min = 0.941, T_max = 0.976	k = −12→12
5265 measured reflections	l = −13→13
3115 independent reflections

Refinement top

Refinement on F²	8 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.141	w = 1/[σ²(F_o²) + (0.0571P)² + 0.4335P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.006
3115 reflections	Δρ_max = 0.28 e Å⁻³
225 parameters	Δρ_min = −0.26 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.3267 (4)	0.4077 (3)	0.6615 (3)	0.0531 (8)
C2	0.3217 (5)	0.2980 (4)	0.6002 (4)	0.0746 (10)
H2	0.2153	0.2759	0.5950	0.089*
C3	0.4765 (7)	0.2216 (4)	0.5467 (4)	0.0934 (13)
H3	0.4733	0.1477	0.5052	0.112*
C4	0.6359 (6)	0.2521 (5)	0.5531 (4)	0.0929 (14)
C5	0.6381 (5)	0.3645 (5)	0.6099 (4)	0.0863 (13)
H5	0.7449	0.3893	0.6108	0.104*
C6	0.4851 (4)	0.4414 (4)	0.6656 (3)	0.0652 (9)
H6	0.4889	0.5160	0.7059	0.078*
C7	−0.0626 (3)	0.3333 (3)	0.8958 (3)	0.0552 (8)
H7A	−0.0428	0.2674	0.9601	0.066*
H7B	−0.0510	0.2884	0.8200	0.066*
C8	−0.2477 (3)	0.4048 (3)	0.9366 (3)	0.0410 (6)
C9	−0.4635 (4)	0.1560 (3)	0.8824 (3)	0.0458 (7)
H9	−0.5775	0.1991	0.9048	0.055*
C10	−0.4289 (4)	0.0216 (3)	0.8385 (3)	0.0441 (7)
C11	−0.5630 (4)	−0.0429 (3)	0.8232 (3)	0.0504 (7)
C12	−0.5183 (5)	−0.1718 (3)	0.7823 (3)	0.0635 (9)
H12	−0.6054	−0.2162	0.7707	0.076*
C13	−0.3499 (5)	−0.2332 (3)	0.7591 (4)	0.0707 (10)
H13	−0.3242	−0.3186	0.7321	0.085*
C14	−0.2182 (5)	−0.1709 (3)	0.7750 (4)	0.0704 (10)
H14	−0.1039	−0.2137	0.7599	0.084*
C15	−0.2575 (4)	−0.0438 (3)	0.8136 (3)	0.0576 (8)
H15	−0.1681	−0.0007	0.8232	0.069*
C16	0.8040 (7)	0.1637 (5)	0.4972 (5)	0.1340 (19)
H16A	0.7763	0.0839	0.4733	0.201*
H16B	0.8717	0.1437	0.5580	0.201*
H16C	0.8704	0.2078	0.4248	0.201*
C17	−0.7500 (4)	0.0184 (3)	0.8499 (4)	0.0708 (10)
H17A	−0.8199	−0.0420	0.8323	0.106*
H17B	−0.7602	0.0972	0.7983	0.106*
H17C	−0.7901	0.0393	0.9364	0.106*
N1	0.0695 (3)	0.4192 (3)	0.8728 (3)	0.0584 (7)
H1N	0.117 (4)	0.434 (3)	0.928 (3)	0.070*
N2	−0.3764 (3)	0.3385 (2)	0.9324 (2)	0.0452 (6)
H2N	−0.484 (2)	0.373 (3)	0.959 (3)	0.054*
N3	−0.3362 (3)	0.2126 (2)	0.8894 (2)	0.0448 (6)
O1	0.0009 (3)	0.4970 (3)	0.6754 (3)	0.0814 (8)
O2	0.1736 (3)	0.6208 (2)	0.7693 (3)	0.0779 (8)
O3	−0.2783 (2)	0.51737 (17)	0.9738 (2)	0.0505 (5)
S1	0.13061 (10)	0.49880 (8)	0.74192 (9)	0.0576 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0511 (18)	0.0503 (18)	0.0533 (19)	−0.0046 (14)	−0.0075 (14)	0.0021 (15)
C2	0.073 (2)	0.072 (2)	0.073 (3)	−0.0126 (19)	−0.0026 (19)	−0.015 (2)
C3	0.120 (4)	0.067 (3)	0.070 (3)	0.006 (2)	0.008 (3)	−0.013 (2)
C4	0.079 (3)	0.106 (4)	0.060 (3)	0.028 (3)	0.012 (2)	0.021 (2)
C5	0.054 (2)	0.119 (4)	0.073 (3)	0.000 (2)	−0.0066 (19)	0.022 (3)
C6	0.0460 (19)	0.075 (2)	0.071 (2)	−0.0074 (16)	−0.0118 (16)	0.0067 (18)
C7	0.0345 (15)	0.0471 (17)	0.081 (2)	−0.0023 (12)	−0.0066 (14)	−0.0174 (16)
C8	0.0323 (14)	0.0387 (16)	0.0503 (17)	−0.0039 (12)	−0.0074 (12)	−0.0036 (13)
C9	0.0381 (15)	0.0389 (16)	0.0580 (19)	−0.0016 (12)	−0.0089 (13)	−0.0054 (13)
C10	0.0470 (16)	0.0340 (15)	0.0510 (18)	−0.0087 (12)	−0.0103 (13)	−0.0015 (13)
C11	0.0549 (18)	0.0410 (16)	0.0568 (19)	−0.0098 (13)	−0.0162 (15)	0.0008 (14)
C12	0.076 (2)	0.0443 (18)	0.077 (2)	−0.0181 (16)	−0.0252 (19)	−0.0066 (16)
C13	0.082 (3)	0.0419 (19)	0.087 (3)	−0.0032 (17)	−0.020 (2)	−0.0126 (18)
C14	0.063 (2)	0.050 (2)	0.089 (3)	0.0090 (16)	−0.0111 (19)	−0.0132 (19)
C15	0.0499 (18)	0.0430 (17)	0.075 (2)	−0.0011 (14)	−0.0085 (16)	−0.0098 (16)
C16	0.118 (3)	0.132 (3)	0.113 (3)	0.043 (3)	0.002 (2)	0.004 (3)
C17	0.054 (2)	0.067 (2)	0.097 (3)	−0.0127 (16)	−0.0249 (19)	−0.006 (2)
N1	0.0384 (14)	0.0756 (18)	0.0637 (19)	−0.0194 (12)	−0.0066 (12)	−0.0165 (15)
N2	0.0315 (12)	0.0340 (12)	0.0678 (17)	−0.0010 (10)	−0.0076 (11)	−0.0119 (11)
N3	0.0409 (13)	0.0310 (12)	0.0610 (16)	−0.0019 (10)	−0.0103 (11)	−0.0084 (11)
O1	0.0602 (15)	0.0930 (19)	0.099 (2)	0.0009 (13)	−0.0384 (14)	−0.0123 (16)
O2	0.0739 (16)	0.0413 (13)	0.119 (2)	−0.0044 (11)	−0.0254 (15)	−0.0112 (13)
O3	0.0393 (11)	0.0349 (11)	0.0787 (15)	−0.0017 (8)	−0.0153 (10)	−0.0159 (10)
S1	0.0435 (4)	0.0522 (5)	0.0781 (6)	−0.0020 (3)	−0.0178 (4)	−0.0089 (4)

Geometric parameters (Å, º) top

C1—C6	1.375 (4)	C10—C15	1.398 (4)
C1—C2	1.380 (4)	C11—C12	1.405 (4)
C1—S1	1.758 (3)	C11—C17	1.492 (4)
C2—C3	1.377 (5)	C12—C13	1.364 (5)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.378 (6)	C13—C14	1.369 (5)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.370 (6)	C14—C15	1.378 (4)
C4—C16	1.516 (6)	C14—H14	0.9300
C5—C6	1.376 (5)	C15—H15	0.9300
C5—H5	0.9300	C16—H16A	0.9600
C6—H6	0.9300	C16—H16B	0.9600
C7—N1	1.440 (4)	C16—H16C	0.9600
C7—C8	1.518 (4)	C17—H17A	0.9600
C7—H7A	0.9700	C17—H17B	0.9600
C7—H7B	0.9700	C17—H17C	0.9600
C8—O3	1.233 (3)	N1—S1	1.604 (3)
C8—N2	1.331 (3)	N1—H1N	0.838 (17)
C9—N3	1.270 (3)	N2—N3	1.384 (3)
C9—C10	1.470 (4)	N2—H2N	0.858 (17)
C9—H9	0.9300	O1—S1	1.422 (2)
C10—C11	1.397 (4)	O2—S1	1.431 (2)

C6—C1—C2	119.9 (3)	C13—C12—H12	119.3
C6—C1—S1	120.0 (2)	C11—C12—H12	119.3
C2—C1—S1	120.0 (3)	C12—C13—C14	120.9 (3)
C3—C2—C1	119.1 (4)	C12—C13—H13	119.5
C3—C2—H2	120.4	C14—C13—H13	119.5
C1—C2—H2	120.4	C13—C14—C15	119.0 (3)
C2—C3—C4	121.6 (4)	C13—C14—H14	120.5
C2—C3—H3	119.2	C15—C14—H14	120.5
C4—C3—H3	119.2	C14—C15—C10	121.4 (3)
C5—C4—C3	118.2 (4)	C14—C15—H15	119.3
C5—C4—C16	121.3 (5)	C10—C15—H15	119.3
C3—C4—C16	120.5 (5)	C4—C16—H16A	109.5
C4—C5—C6	121.2 (4)	C4—C16—H16B	109.5
C4—C5—H5	119.4	H16A—C16—H16B	109.5
C6—C5—H5	119.4	C4—C16—H16C	109.5
C1—C6—C5	119.8 (4)	H16A—C16—H16C	109.5
C1—C6—H6	120.1	H16B—C16—H16C	109.5
C5—C6—H6	120.1	C11—C17—H17A	109.5
N1—C7—C8	113.2 (2)	C11—C17—H17B	109.5
N1—C7—H7A	108.9	H17A—C17—H17B	109.5
C8—C7—H7A	108.9	C11—C17—H17C	109.5
N1—C7—H7B	108.9	H17A—C17—H17C	109.5
C8—C7—H7B	108.9	H17B—C17—H17C	109.5
H7A—C7—H7B	107.7	C7—N1—S1	122.9 (2)
O3—C8—N2	121.5 (2)	C7—N1—H1N	122 (2)
O3—C8—C7	122.1 (2)	S1—N1—H1N	115 (2)
N2—C8—C7	116.5 (2)	C8—N2—N3	119.6 (2)
N3—C9—C10	119.4 (2)	C8—N2—H2N	120 (2)
N3—C9—H9	120.3	N3—N2—H2N	120 (2)
C10—C9—H9	120.3	C9—N3—N2	117.0 (2)
C11—C10—C15	119.3 (3)	O1—S1—O2	120.42 (15)
C11—C10—C9	121.8 (2)	O1—S1—N1	106.98 (15)
C15—C10—C9	118.9 (2)	O2—S1—N1	107.14 (15)
C10—C11—C12	117.9 (3)	O1—S1—C1	108.74 (15)
C10—C11—C17	123.0 (3)	O2—S1—C1	107.04 (15)
C12—C11—C17	119.1 (3)	N1—S1—C1	105.61 (15)
C13—C12—C11	121.4 (3)

C6—C1—C2—C3	1.8 (5)	C11—C12—C13—C14	0.0 (6)
S1—C1—C2—C3	−174.6 (3)	C12—C13—C14—C15	−0.7 (6)
C1—C2—C3—C4	0.1 (6)	C13—C14—C15—C10	1.0 (5)
C2—C3—C4—C5	−2.8 (6)	C11—C10—C15—C14	−0.5 (5)
C2—C3—C4—C16	177.9 (4)	C9—C10—C15—C14	178.5 (3)
C3—C4—C5—C6	3.7 (6)	C8—C7—N1—S1	−84.6 (3)
C16—C4—C5—C6	−177.0 (4)	O3—C8—N2—N3	179.7 (3)
C2—C1—C6—C5	−0.9 (5)	C7—C8—N2—N3	−1.5 (4)
S1—C1—C6—C5	175.5 (3)	C10—C9—N3—N2	−179.4 (2)
C4—C5—C6—C1	−1.9 (6)	C8—N2—N3—C9	−177.1 (3)
N1—C7—C8—O3	−15.8 (4)	C7—N1—S1—O1	16.2 (3)
N1—C7—C8—N2	165.4 (3)	C7—N1—S1—O2	146.6 (2)
N3—C9—C10—C11	−176.8 (3)	C7—N1—S1—C1	−99.6 (3)
N3—C9—C10—C15	4.3 (4)	C6—C1—S1—O1	148.8 (3)
C15—C10—C11—C12	−0.3 (4)	C2—C1—S1—O1	−34.8 (3)
C9—C10—C11—C12	−179.3 (3)	C6—C1—S1—O2	17.2 (3)
C15—C10—C11—C17	178.8 (3)	C2—C1—S1—O2	−166.4 (3)
C9—C10—C11—C17	−0.2 (5)	C6—C1—S1—N1	−96.7 (3)
C10—C11—C12—C13	0.5 (5)	C2—C1—S1—N1	79.7 (3)
C17—C11—C12—C13	−178.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3ⁱ	0.84 (2)	2.03 (2)	2.845 (3)	166 (3)
N2—H2N···O3ⁱⁱ	0.86 (2)	2.05 (2)	2.898 (3)	170 (3)

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

(E)-N-{2-[2-(2-Nitrobenzylidene)hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide (III) top

Crystal data top

C₁₆H₁₆N₄O₅S	Z = 2
M_r = 376.39	F(000) = 392
Triclinic, P1	D_x = 1.446 Mg m⁻³
a = 8.006 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.229 (1) Å	Cell parameters from 1476 reflections
c = 11.181 (2) Å	θ = 2.7–27.9°
α = 83.76 (1)°	µ = 0.22 mm⁻¹
β = 72.86 (1)°	T = 293 K
γ = 82.13 (1)°	Rod, light yellow
V = 864.5 (2) Å³	0.48 × 0.48 × 0.28 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2511 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	R_int = 0.020
Rotation method data acquisition using ω scans	θ_max = 26.4°, θ_min = 2.7°
Absorption correction: multi-scan CrysAlis RED (Oxford Diffraction, 2009)	h = −10→10
T_min = 0.900, T_max = 0.940	k = −8→12
5980 measured reflections	l = −13→13
3524 independent reflections

Refinement top

Refinement on F²	10 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.131	w = 1/[σ²(F_o²) + (0.0346P)² + 0.6348P] where P = (F_o² + 2F_c²)/3
S = 1.16	(Δ/σ)_max < 0.001
3524 reflections	Δρ_max = 0.31 e Å⁻³
252 parameters	Δρ_min = −0.30 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.1583 (4)	0.0902 (3)	0.3328 (3)	0.0432 (7)
C2	0.0013 (4)	0.0489 (3)	0.3328 (3)	0.0515 (7)
H2	0.0012	−0.0291	0.2972	0.062*
C3	−0.1551 (4)	0.1232 (4)	0.3853 (3)	0.0646 (9)
H3	−0.2603	0.0939	0.3857	0.078*
C4	−0.1592 (5)	0.2390 (4)	0.4367 (3)	0.0679 (9)
C5	−0.0013 (5)	0.2782 (3)	0.4388 (3)	0.0695 (9)
H5	−0.0021	0.3558	0.4754	0.083*
C6	0.1581 (5)	0.2045 (3)	0.3877 (3)	0.0603 (8)
H6	0.2630	0.2317	0.3903	0.072*
C7	0.5648 (3)	0.1686 (3)	0.1001 (3)	0.0490 (7)
H7A	0.5499	0.2132	0.1754	0.059*
H7B	0.5508	0.2354	0.0342	0.059*
C8	0.7488 (3)	0.0959 (2)	0.0614 (2)	0.0364 (6)
C9	0.9667 (3)	0.3431 (2)	0.1185 (2)	0.0380 (6)
H9A	1.0802	0.2998	0.1013	0.046*
C10	0.9269 (3)	0.4777 (2)	0.1623 (2)	0.0362 (6)
C11	1.0452 (3)	0.5481 (3)	0.1918 (3)	0.0416 (6)
C12	0.9983 (4)	0.6727 (3)	0.2364 (3)	0.0543 (8)
H12	1.0797	0.7158	0.2574	0.065*
C13	0.8299 (4)	0.7322 (3)	0.2493 (3)	0.0584 (9)
H13	0.7974	0.8166	0.2778	0.070*
C14	0.7102 (4)	0.6671 (3)	0.2202 (3)	0.0544 (8)
H14	0.5966	0.7079	0.2283	0.065*
C15	0.7571 (4)	0.5416 (3)	0.1790 (3)	0.0446 (7)
H15	0.6730	0.4981	0.1618	0.054*
C16	−0.3304 (6)	0.3242 (5)	0.4884 (4)	0.1112 (18)
H16A	−0.4218	0.2687	0.5278	0.167*
H16B	−0.3609	0.3795	0.4212	0.167*
H16C	−0.3172	0.3787	0.5490	0.167*
N1	0.4300 (3)	0.0805 (3)	0.1237 (2)	0.0496 (6)
H1N	0.385 (4)	0.071 (3)	0.066 (2)	0.059*
N2	0.8798 (3)	0.1627 (2)	0.0649 (2)	0.0386 (5)
H2N	0.987 (2)	0.125 (3)	0.043 (3)	0.046*
N3	0.8416 (3)	0.2882 (2)	0.1050 (2)	0.0385 (5)
N4	1.2287 (3)	0.4938 (3)	0.1766 (3)	0.0599 (7)
O1	0.3169 (3)	−0.12378 (19)	0.2315 (2)	0.0650 (6)
O2	0.4818 (3)	0.0038 (2)	0.3249 (2)	0.0692 (7)
O3	0.7787 (2)	−0.01737 (17)	0.02690 (19)	0.0447 (5)
O4	1.3001 (3)	0.4196 (3)	0.0977 (3)	0.0919 (9)
O5	1.2976 (6)	0.5163 (5)	0.2569 (6)	0.102 (2)	0.836 (12)
O5'	1.3314 (19)	0.5818 (18)	0.157 (3)	0.083 (9)	0.164 (12)
S1	0.35831 (9)	0.00025 (7)	0.25622 (8)	0.0478 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0411 (15)	0.0425 (15)	0.0418 (16)	−0.0022 (12)	−0.0074 (12)	−0.0006 (13)
C2	0.0421 (16)	0.0555 (18)	0.0552 (19)	−0.0072 (14)	−0.0111 (14)	−0.0017 (15)
C3	0.0407 (18)	0.085 (3)	0.060 (2)	−0.0004 (17)	−0.0080 (15)	0.0025 (19)
C4	0.0641 (19)	0.078 (2)	0.0408 (18)	0.0169 (17)	0.0032 (16)	0.0048 (17)
C5	0.090 (2)	0.057 (2)	0.0508 (19)	0.0026 (18)	−0.0040 (19)	−0.0157 (16)
C6	0.060 (2)	0.061 (2)	0.058 (2)	−0.0107 (16)	−0.0077 (16)	−0.0144 (16)
C7	0.0309 (14)	0.0424 (16)	0.070 (2)	−0.0009 (12)	−0.0063 (13)	−0.0154 (14)
C8	0.0307 (13)	0.0356 (14)	0.0419 (15)	−0.0021 (11)	−0.0087 (11)	−0.0046 (12)
C9	0.0307 (13)	0.0351 (14)	0.0472 (16)	−0.0013 (11)	−0.0093 (12)	−0.0056 (12)
C10	0.0356 (14)	0.0303 (13)	0.0410 (15)	−0.0035 (11)	−0.0086 (11)	−0.0022 (11)
C11	0.0374 (15)	0.0353 (14)	0.0529 (17)	−0.0041 (11)	−0.0140 (13)	−0.0027 (13)
C12	0.0551 (19)	0.0406 (16)	0.072 (2)	−0.0115 (14)	−0.0204 (16)	−0.0126 (15)
C13	0.060 (2)	0.0361 (16)	0.076 (2)	0.0019 (14)	−0.0137 (17)	−0.0178 (15)
C14	0.0436 (17)	0.0430 (17)	0.071 (2)	0.0059 (13)	−0.0108 (15)	−0.0110 (15)
C15	0.0351 (14)	0.0405 (15)	0.0577 (18)	−0.0037 (12)	−0.0110 (13)	−0.0083 (13)
C16	0.090 (3)	0.122 (4)	0.078 (3)	0.047 (3)	0.013 (2)	0.001 (3)
N1	0.0324 (13)	0.0623 (16)	0.0556 (16)	−0.0106 (11)	−0.0081 (11)	−0.0166 (13)
N2	0.0278 (11)	0.0345 (12)	0.0523 (14)	0.0000 (9)	−0.0079 (10)	−0.0115 (10)
N3	0.0342 (12)	0.0303 (11)	0.0497 (14)	−0.0017 (9)	−0.0090 (10)	−0.0077 (10)
N4	0.0433 (15)	0.0456 (15)	0.100 (2)	−0.0046 (12)	−0.0302 (16)	−0.0160 (15)
O1	0.0550 (13)	0.0384 (11)	0.1000 (18)	−0.0020 (10)	−0.0181 (13)	−0.0126 (11)
O2	0.0496 (13)	0.0867 (17)	0.0790 (16)	0.0004 (12)	−0.0331 (12)	−0.0076 (13)
O3	0.0331 (10)	0.0361 (10)	0.0667 (13)	0.0007 (8)	−0.0142 (9)	−0.0177 (9)
O4	0.0441 (14)	0.0826 (18)	0.153 (3)	0.0129 (13)	−0.0299 (16)	−0.0465 (19)
O5	0.077 (3)	0.109 (4)	0.154 (5)	0.002 (2)	−0.076 (3)	−0.042 (4)
O5'	0.046 (8)	0.069 (11)	0.139 (19)	−0.014 (7)	−0.027 (9)	−0.020 (11)
S1	0.0350 (4)	0.0450 (4)	0.0644 (5)	−0.0004 (3)	−0.0156 (3)	−0.0093 (3)

Geometric parameters (Å, º) top

C1—C6	1.377 (4)	C10—C11	1.395 (4)
C1—C2	1.380 (4)	C11—C12	1.383 (4)
C1—S1	1.762 (3)	C11—N4	1.464 (4)
C2—C3	1.376 (4)	C12—C13	1.373 (4)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.364 (5)	C13—C14	1.369 (4)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.385 (5)	C14—C15	1.377 (4)
C4—C16	1.513 (5)	C14—H14	0.9300
C5—C6	1.387 (5)	C15—H15	0.9300
C5—H5	0.9300	C16—H16A	0.9600
C6—H6	0.9300	C16—H16B	0.9600
C7—N1	1.446 (4)	C16—H16C	0.9600
C7—C8	1.518 (3)	N1—S1	1.600 (3)
C7—H7A	0.9700	N1—H1N	0.845 (17)
C7—H7B	0.9700	N2—N3	1.371 (3)
C8—O3	1.232 (3)	N2—H2N	0.865 (17)
C8—N2	1.340 (3)	N4—O4	1.188 (3)
C9—N3	1.266 (3)	N4—O5	1.239 (4)
C9—C10	1.474 (3)	N4—O5'	1.260 (13)
C9—H9A	0.9300	O1—S1	1.429 (2)
C10—C15	1.394 (4)	O2—S1	1.426 (2)

C6—C1—C2	119.9 (3)	C10—C11—N4	121.6 (2)
C6—C1—S1	120.4 (2)	C13—C12—C11	119.2 (3)
C2—C1—S1	119.6 (2)	C13—C12—H12	120.4
C3—C2—C1	120.0 (3)	C11—C12—H12	120.4
C3—C2—H2	120.0	C14—C13—C12	120.0 (3)
C1—C2—H2	120.0	C14—C13—H13	120.0
C4—C3—C2	121.4 (3)	C12—C13—H13	120.0
C4—C3—H3	119.3	C13—C14—C15	120.3 (3)
C2—C3—H3	119.3	C13—C14—H14	119.8
C3—C4—C5	118.2 (3)	C15—C14—H14	119.8
C3—C4—C16	121.4 (4)	C14—C15—C10	122.0 (3)
C5—C4—C16	120.4 (4)	C14—C15—H15	119.0
C4—C5—C6	121.5 (3)	C10—C15—H15	119.0
C4—C5—H5	119.2	C4—C16—H16A	109.5
C6—C5—H5	119.2	C4—C16—H16B	109.5
C1—C6—C5	118.9 (3)	H16A—C16—H16B	109.5
C1—C6—H6	120.6	C4—C16—H16C	109.5
C5—C6—H6	120.6	H16A—C16—H16C	109.5
N1—C7—C8	112.3 (2)	H16B—C16—H16C	109.5
N1—C7—H7A	109.1	C7—N1—S1	122.9 (2)
C8—C7—H7A	109.1	C7—N1—H1N	119 (2)
N1—C7—H7B	109.1	S1—N1—H1N	118 (2)
C8—C7—H7B	109.1	C8—N2—N3	119.4 (2)
H7A—C7—H7B	107.9	C8—N2—H2N	119.2 (19)
O3—C8—N2	121.0 (2)	N3—N2—H2N	121.4 (19)
O3—C8—C7	122.7 (2)	C9—N3—N2	117.5 (2)
N2—C8—C7	116.3 (2)	O4—N4—C11	120.1 (3)
N3—C9—C10	118.0 (2)	O5—N4—C11	117.5 (3)
N3—C9—H9A	121.0	O5'—N4—C11	113.1 (9)
C10—C9—H9A	121.0	O2—S1—O1	120.10 (15)
C15—C10—C11	115.8 (2)	O2—S1—N1	106.98 (14)
C15—C10—C9	118.8 (2)	O1—S1—N1	107.32 (14)
C11—C10—C9	125.4 (2)	O2—S1—C1	108.77 (14)
C12—C11—C10	122.7 (3)	O1—S1—C1	107.00 (13)
C12—C11—N4	115.7 (3)	N1—S1—C1	105.82 (13)

C6—C1—C2—C3	1.2 (5)	C11—C10—C15—C14	1.0 (4)
S1—C1—C2—C3	−175.8 (2)	C9—C10—C15—C14	179.7 (3)
C1—C2—C3—C4	0.8 (5)	C8—C7—N1—S1	85.4 (3)
C2—C3—C4—C5	−2.2 (5)	O3—C8—N2—N3	−179.4 (2)
C2—C3—C4—C16	176.8 (3)	C7—C8—N2—N3	1.6 (4)
C3—C4—C5—C6	1.5 (5)	C10—C9—N3—N2	−179.7 (2)
C16—C4—C5—C6	−177.4 (3)	C8—N2—N3—C9	173.4 (2)
C2—C1—C6—C5	−1.9 (5)	C12—C11—N4—O4	−149.9 (3)
S1—C1—C6—C5	175.2 (3)	C10—C11—N4—O4	29.8 (5)
C4—C5—C6—C1	0.5 (5)	C12—C11—N4—O5	38.0 (5)
N1—C7—C8—O3	15.4 (4)	C10—C11—N4—O5	−142.3 (5)
N1—C7—C8—N2	−165.5 (2)	C12—C11—N4—O5'	−27.0 (16)
N3—C9—C10—C15	−4.1 (4)	C10—C11—N4—O5'	152.6 (16)
N3—C9—C10—C11	174.5 (3)	C7—N1—S1—O2	−15.9 (3)
C15—C10—C11—C12	0.7 (4)	C7—N1—S1—O1	−146.1 (2)
C9—C10—C11—C12	−177.9 (3)	C7—N1—S1—C1	99.9 (2)
C15—C10—C11—N4	−178.9 (3)	C6—C1—S1—O2	37.8 (3)
C9—C10—C11—N4	2.5 (4)	C2—C1—S1—O2	−145.2 (2)
C10—C11—C12—C13	−1.8 (5)	C6—C1—S1—O1	168.9 (2)
N4—C11—C12—C13	177.9 (3)	C2—C1—S1—O1	−14.0 (3)
C11—C12—C13—C14	1.1 (5)	C6—C1—S1—N1	−76.8 (3)
C12—C13—C14—C15	0.6 (5)	C2—C1—S1—N1	100.2 (2)
C13—C14—C15—C10	−1.7 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3ⁱ	0.85 (2)	2.06 (2)	2.869 (3)	161 (3)
N2—H2N···O3ⁱⁱ	0.87 (2)	2.03 (2)	2.881 (3)	170 (3)
C7—H7B···O4ⁱⁱⁱ	0.97	2.55	3.100 (4)	116
C9—H9A···O4	0.93	2.27	2.821 (4)	118
C16—H16C···O5^iv	0.96	2.58	3.525 (6)	168

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

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Crystal structures of three ortho-substituted N-acyl­hydrazone derivatives

Supporting information

Key indicators

checkCIF/PLATON results

Crystal structures of three ortho-substituted N-acylhydrazone derivatives