(E)-1-(2,6-Di­chloro­phen­yl)-2-(3-nitro­benzyl­idene)hydrazine: crystal structure and Hirshfeld surface analysis

In the crystal, face-to-face π-π stacking inter­actions along the a-axis direction occur between the 2,6-di­chloro­phenyl ring and nitro-substituted benzene ring of the title mol­ecule. The mol­ecules are further linked by C—H...O contacts and N—H...O and C—H...Cl hydrogen bonds, forming pairs of hydrogen-bonded mol­ecular layers parallel to (100).

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.031
• wR factor = 0.064
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00415 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          5 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          2 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          2 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
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   0 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
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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Computing details

Data collection: APEX3 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXT2016/6 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: PLATON (Spek, 2020).

(E)-1-(2,6-Dichlorophenyl)-2-(3-nitrobenzylidene)hydrazine

Crystal data

C13H9Cl2N3O2	F(000) = 316
Mr = 310.13	Dx = 1.537 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 7.1212 (14) Å	Cell parameters from 9800 reflections
b = 12.711 (3) Å	θ = 2.8–26.3°
c = 7.6991 (16) Å	µ = 0.49 mm^−1
β = 105.940 (7)°	T = 296 K
V = 670.1 (2) Å^3	Plate, orange
Z = 2	0.26 × 0.22 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer	2392 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.062
Absorption correction: multi-scan (SADABS; Bruker, 2003)	θmax = 26.4°, θmin = 2.8°
Tmin = 0.873, Tmax = 0.902	h = −8→8
22230 measured reflections	k = −15→15
2744 independent reflections	l = −9→9

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.031	H-atom parameters constrained
wR(F^2) = 0.064	w = 1/[σ^2(Fo^2) + (0.0217P)^2 + 0.0759P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max < 0.001
2744 reflections	Δρmax = 0.15 e Å^−3
181 parameters	Δρmin = −0.16 e Å^−3
1 restraint	Absolute structure: Flack x determined using 1032 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (3)

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
Cl1	0.28649 (13)	0.12020 (5)	0.58310 (10)	0.0583 (2)
Cl2	0.28511 (15)	0.43809 (7)	0.10800 (12)	0.0666 (3)
O1	0.3919 (5)	0.7625 (2)	1.1215 (3)	0.0799 (8)
O2	0.2541 (5)	0.9024 (2)	0.9937 (4)	0.0848 (9)
N1	0.3362 (4)	0.34075 (17)	0.4897 (3)	0.0465 (6)
H1N	0.401372	0.310054	0.602708	0.056*
N2	0.2806 (3)	0.44380 (18)	0.4863 (3)	0.0397 (5)
N3	0.3101 (4)	0.8121 (2)	0.9871 (4)	0.0531 (7)
C1	0.2672 (4)	0.2769 (2)	0.3396 (4)	0.0365 (6)
C2	0.2365 (4)	0.1696 (2)	0.3645 (4)	0.0411 (7)
C3	0.1710 (5)	0.1009 (2)	0.2220 (4)	0.0543 (8)
H3A	0.152757	0.030205	0.243822	0.065*
C4	0.1330 (5)	0.1370 (3)	0.0483 (5)	0.0588 (9)
H4A	0.086569	0.091344	−0.048297	0.071*
C5	0.1641 (5)	0.2419 (3)	0.0174 (4)	0.0558 (8)
H5A	0.139312	0.266660	−0.100398	0.067*
C6	0.2322 (4)	0.3105 (2)	0.1614 (4)	0.0426 (7)
C7	0.3439 (5)	0.4963 (2)	0.6318 (4)	0.0413 (7)
H7A	0.421014	0.463484	0.734710	0.050*
C8	0.2957 (4)	0.6082 (2)	0.6376 (3)	0.0359 (6)
C9	0.2219 (5)	0.6675 (2)	0.4811 (4)	0.0433 (7)
H9A	0.201931	0.635668	0.368765	0.052*
C10	0.1784 (5)	0.7724 (2)	0.4908 (4)	0.0512 (8)
H10A	0.131772	0.810787	0.384850	0.061*
C11	0.2029 (5)	0.8214 (2)	0.6557 (4)	0.0475 (7)
H11A	0.169393	0.891678	0.662994	0.057*
C12	0.2790 (4)	0.7623 (2)	0.8092 (4)	0.0387 (6)
C13	0.3274 (4)	0.6576 (2)	0.8048 (4)	0.0375 (6)
H13A	0.380225	0.620594	0.911236	0.045*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0720 (6)	0.0433 (4)	0.0608 (5)	0.0025 (4)	0.0200 (4)	0.0100 (4)
Cl2	0.0988 (8)	0.0470 (4)	0.0610 (5)	0.0050 (5)	0.0339 (5)	0.0121 (4)
O1	0.122 (2)	0.0705 (17)	0.0406 (13)	0.0047 (16)	0.0118 (14)	−0.0139 (12)
O2	0.106 (2)	0.0565 (16)	0.0844 (19)	0.0181 (15)	0.0135 (16)	−0.0350 (14)
N1	0.0622 (17)	0.0308 (12)	0.0418 (13)	0.0081 (10)	0.0060 (11)	−0.0040 (9)
N2	0.0457 (13)	0.0285 (10)	0.0451 (12)	0.0019 (11)	0.0128 (10)	−0.0042 (10)
N3	0.0580 (18)	0.0489 (15)	0.0529 (16)	−0.0065 (13)	0.0163 (14)	−0.0188 (13)
C1	0.0341 (15)	0.0321 (12)	0.0434 (14)	0.0045 (11)	0.0110 (12)	−0.0048 (10)
C2	0.0420 (17)	0.0315 (13)	0.0513 (17)	0.0049 (12)	0.0153 (13)	−0.0011 (11)
C3	0.0538 (19)	0.0350 (16)	0.073 (2)	0.0013 (14)	0.0155 (16)	−0.0127 (15)
C4	0.059 (2)	0.055 (2)	0.0569 (19)	0.0011 (16)	0.0081 (15)	−0.0228 (15)
C5	0.058 (2)	0.066 (2)	0.0420 (17)	0.0124 (17)	0.0099 (15)	−0.0063 (14)
C6	0.0452 (18)	0.0368 (14)	0.0477 (16)	0.0057 (13)	0.0158 (14)	−0.0013 (13)
C7	0.0522 (19)	0.0326 (14)	0.0385 (15)	0.0020 (12)	0.0116 (13)	−0.0017 (11)
C8	0.0366 (14)	0.0336 (13)	0.0379 (13)	−0.0044 (12)	0.0108 (11)	−0.0043 (12)
C9	0.0506 (19)	0.0418 (16)	0.0354 (15)	−0.0022 (13)	0.0080 (13)	−0.0064 (11)
C10	0.059 (2)	0.0423 (16)	0.0455 (18)	0.0014 (15)	0.0033 (15)	0.0060 (13)
C11	0.0504 (19)	0.0295 (13)	0.0594 (19)	0.0028 (13)	0.0097 (15)	−0.0045 (13)
C12	0.0380 (15)	0.0361 (14)	0.0417 (16)	−0.0054 (12)	0.0104 (12)	−0.0109 (11)
C13	0.0422 (16)	0.0355 (13)	0.0355 (14)	−0.0025 (11)	0.0119 (12)	−0.0009 (10)

Geometric parameters (Å, º)

Cl1—C2	1.739 (3)	C4—H4A	0.9300
Cl2—C6	1.740 (3)	C5—C6	1.389 (4)
O1—N3	1.215 (4)	C5—H5A	0.9300
O2—N3	1.220 (4)	C7—C8	1.467 (4)
N1—N2	1.367 (3)	C7—H7A	0.9300
N1—C1	1.387 (3)	C8—C13	1.393 (3)
N1—H1N	0.9500	C8—C9	1.396 (4)
N2—C7	1.275 (3)	C9—C10	1.375 (4)
N3—C12	1.469 (3)	C9—H9A	0.9300
C1—C6	1.392 (4)	C10—C11	1.382 (4)
C1—C2	1.404 (4)	C10—H10A	0.9300
C2—C3	1.379 (4)	C11—C12	1.379 (4)
C3—C4	1.369 (5)	C11—H11A	0.9300
C3—H3A	0.9300	C12—C13	1.378 (4)
C4—C5	1.383 (5)	C13—H13A	0.9300
N2—N1—C1	120.7 (2)	C5—C6—Cl2	116.6 (2)
N2—N1—H1N	118.5	C1—C6—Cl2	121.8 (2)
C1—N1—H1N	119.7	N2—C7—C8	120.4 (3)
C7—N2—N1	117.0 (2)	N2—C7—H7A	119.8
O1—N3—O2	122.6 (3)	C8—C7—H7A	119.8
O1—N3—C12	119.0 (3)	C13—C8—C9	118.7 (2)
O2—N3—C12	118.5 (3)	C13—C8—C7	119.0 (2)
N1—C1—C6	124.6 (2)	C9—C8—C7	122.2 (2)
N1—C1—C2	119.2 (3)	C10—C9—C8	120.9 (3)
C6—C1—C2	116.1 (2)	C10—C9—H9A	119.5
C3—C2—C1	122.5 (3)	C8—C9—H9A	119.5
C3—C2—Cl1	118.4 (2)	C9—C10—C11	120.9 (3)
C1—C2—Cl1	119.0 (2)	C9—C10—H10A	119.6
C4—C3—C2	119.9 (3)	C11—C10—H10A	119.6
C4—C3—H3A	120.1	C12—C11—C10	117.5 (3)
C2—C3—H3A	120.1	C12—C11—H11A	121.2
C3—C4—C5	119.6 (3)	C10—C11—H11A	121.2
C3—C4—H4A	120.2	C13—C12—C11	123.2 (2)
C5—C4—H4A	120.2	C13—C12—N3	117.7 (3)
C4—C5—C6	120.3 (3)	C11—C12—N3	119.1 (2)
C4—C5—H5A	119.8	C12—C13—C8	118.7 (2)
C6—C5—H5A	119.8	C12—C13—H13A	120.7
C5—C6—C1	121.5 (3)	C8—C13—H13A	120.7
C1—N1—N2—C7	177.3 (3)	N1—N2—C7—C8	178.2 (2)
N2—N1—C1—C6	35.6 (4)	N2—C7—C8—C13	165.5 (3)
N2—N1—C1—C2	−147.1 (3)	N2—C7—C8—C9	−15.6 (4)
N1—C1—C2—C3	−179.0 (3)	C13—C8—C9—C10	−1.0 (4)
C6—C1—C2—C3	−1.5 (4)	C7—C8—C9—C10	−179.9 (3)
N1—C1—C2—Cl1	−0.1 (4)	C8—C9—C10—C11	−1.3 (5)
C6—C1—C2—Cl1	177.4 (2)	C9—C10—C11—C12	2.3 (5)
C1—C2—C3—C4	−0.2 (5)	C10—C11—C12—C13	−1.2 (4)
Cl1—C2—C3—C4	−179.1 (3)	C10—C11—C12—N3	179.1 (3)
C2—C3—C4—C5	1.2 (5)	O1—N3—C12—C13	6.2 (4)
C3—C4—C5—C6	−0.4 (5)	O2—N3—C12—C13	−174.4 (3)
C4—C5—C6—C1	−1.4 (5)	O1—N3—C12—C11	−174.0 (3)
C4—C5—C6—Cl2	175.0 (3)	O2—N3—C12—C11	5.4 (4)
N1—C1—C6—C5	179.6 (3)	C11—C12—C13—C8	−1.0 (4)
C2—C1—C6—C5	2.3 (4)	N3—C12—C13—C8	178.8 (3)
N1—C1—C6—Cl2	3.4 (4)	C9—C8—C13—C12	2.0 (4)
C2—C1—C6—Cl2	−173.9 (2)	C7—C8—C13—C12	−179.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···Cl1	0.95	2.54	2.940 (2)	106
N1—H1N···O1^i	0.95	2.31	3.243 (3)	168

Symmetry code: (i) −x+1, y−1/2, −z+2.