Crystal structure of 4-[(4-methyl­benz­yl)­oxy]-N′-(4-nitro­benzyl­idene)benzohydrazide: a new hydrazone derivative

The title aroylhydrazone ether exists in an E-configuration with respect to the double bond of the hydrazone bridge and with an ac­yl–hydrazone (—CH=N—NH—CO—) torsion angle of 166.0 (3)°. The mol­ecule exhibits a non-planar conformation, likely induced by packing requirements.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.053
• wR factor = 0.126
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C
STRVA01_ALERT_4_C           Flack parameter is too small
           From the CIF: _refine_ls_abs_structure_Flack   -0.800
           From the CIF: _refine_ls_abs_structure_Flack_su    0.900
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         C2 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         C5 Check
PLAT334_ALERT_2_C Small <C-C> Benzene Dist.   C2       -C7       .       1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00541 Ang.
PLAT430_ALERT_2_C Short Inter D...A Contact  O4       ..N3       .       2.88 Ang.
                                               1-x,1/2+y,-z  =      2_655 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.301 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report
PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage         72 %

Alert level G
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .      0.900 Report
PLAT480_ALERT_4_G Long H...A H-Bond Reported H14      ..N2       .       2.68 Ang.
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          2 Note
PLAT916_ALERT_2_G Hooft y and Flack x Parameter Values Differ by .       0.10 Check
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          2 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        3.8 Low
PLAT965_ALERT_2_G The SHELXL WEIGHT Optimisation has not Converged     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          5 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   9 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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 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

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Computing details

Data collection: RAPID-AUTO (Rigaku, 2018); cell refinement: RAPID-AUTO (Rigaku, 2018); data reduction: RAPID-AUTO (Rigaku, 2018); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 2012).

4-[(4-Methylbenzyl)oxy]-N'-(4-nitrobenzylidene)benzohydrazide

Crystal data

C22H19N3O4	F(000) = 408
Mr = 389.40	Dx = 1.372 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71075 Å
a = 8.9485 (8) Å	Cell parameters from 5984 reflections
b = 5.0612 (5) Å	θ = 2.3–27.5°
c = 20.949 (2) Å	µ = 0.10 mm^−1
β = 96.585 (7)°	T = 173 K
V = 942.54 (16) Å^3	Platel, colorless
Z = 2	0.30 × 0.28 × 0.03 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	2635 reflections with I > 2σ(I)
Detector resolution: 10.000 pixels mm^-1	Rint = 0.050
ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −11→11
Tmin = 0.749, Tmax = 0.997	k = −5→6
9086 measured reflections	l = −27→27
3799 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.053	w = 1/[σ^2(Fo^2) + (0.0637P)^2 + 0.0221P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.126	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.19 e Å^−3
3799 reflections	Δρmin = −0.16 e Å^−3
266 parameters	Absolute structure: Flack x determined using 741 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: −0.8 (9)

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
O1	0.1477 (3)	0.5424 (5)	0.66816 (11)	0.0476 (7)
O2	0.3072 (3)	0.1188 (5)	0.39878 (10)	0.0407 (6)
O3	0.7195 (4)	0.3955 (11)	0.04333 (15)	0.0967 (14)
O4	0.5966 (4)	0.7477 (8)	0.00909 (14)	0.0786 (10)
N1	0.3611 (4)	0.5542 (5)	0.38830 (13)	0.0369 (7)
H1	0.354 (4)	0.724 (8)	0.4011 (17)	0.044*
N2	0.4173 (3)	0.5102 (5)	0.33080 (12)	0.0359 (7)
N3	0.6379 (4)	0.5860 (10)	0.05105 (16)	0.0632 (11)
C1	−0.1011 (5)	0.8823 (12)	0.93031 (19)	0.0716 (14)
H1A	−0.136189	1.063016	0.920871	0.086*
H1B	−0.010078	0.886972	0.961152	0.086*
H1C	−0.179652	0.782238	0.948641	0.086*
C2	−0.0660 (4)	0.7506 (9)	0.86904 (16)	0.0472 (10)
C3	0.0290 (5)	0.5425 (10)	0.86983 (18)	0.0648 (13)
H3	0.074131	0.476727	0.909949	0.078*
C4	0.0622 (5)	0.4232 (10)	0.81397 (18)	0.0661 (13)
H4	0.130000	0.278228	0.816291	0.079*
C5	−0.0019 (4)	0.5115 (8)	0.75470 (16)	0.0401 (8)
C6	−0.0974 (5)	0.7189 (9)	0.75353 (18)	0.0554 (11)
H6	−0.143298	0.783136	0.713380	0.067*
C7	−0.1295 (5)	0.8387 (11)	0.80936 (19)	0.0655 (13)
H7	−0.196585	0.984825	0.806939	0.079*
C8	0.0349 (4)	0.3846 (8)	0.69368 (16)	0.0462 (9)
H8A	0.072933	0.203070	0.702463	0.055*
H8B	−0.056490	0.374539	0.662284	0.055*
C9	0.1823 (4)	0.4840 (7)	0.60809 (15)	0.0360 (8)
C10	0.1222 (4)	0.2735 (7)	0.57052 (15)	0.0387 (9)
H10	0.052049	0.156850	0.586470	0.046*
C11	0.1652 (4)	0.2362 (7)	0.51033 (15)	0.0382 (8)
H11	0.123802	0.092481	0.485007	0.046*
C12	0.2679 (4)	0.4034 (6)	0.48530 (15)	0.0311 (8)
C13	0.3289 (4)	0.6103 (7)	0.52395 (15)	0.0388 (8)
H13	0.399403	0.727021	0.508241	0.047*
C14	0.2876 (4)	0.6465 (7)	0.58475 (16)	0.0419 (9)
H14	0.332136	0.785035	0.610979	0.050*
C15	0.3126 (4)	0.3454 (7)	0.42105 (15)	0.0318 (8)
C16	0.4317 (4)	0.7143 (7)	0.29601 (16)	0.0410 (8)
H16	0.404496	0.884332	0.310034	0.049*
C17	0.4910 (4)	0.6807 (7)	0.23383 (16)	0.0405 (9)
C18	0.5876 (5)	0.4754 (8)	0.22322 (18)	0.0463 (9)
H18	0.620600	0.356662	0.257043	0.056*
C19	0.6358 (5)	0.4437 (9)	0.16319 (18)	0.0509 (10)
H19	0.702781	0.304857	0.155381	0.061*
C20	0.5843 (4)	0.6185 (9)	0.11485 (17)	0.0491 (10)
C21	0.4894 (5)	0.8217 (8)	0.12357 (17)	0.0545 (11)
H21	0.455193	0.937239	0.089234	0.065*
C22	0.4445 (5)	0.8546 (8)	0.18362 (17)	0.0526 (10)
H22	0.380496	0.998273	0.191162	0.063*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0515 (15)	0.0606 (18)	0.0328 (13)	−0.0128 (14)	0.0139 (11)	−0.0079 (12)
O2	0.0605 (16)	0.0307 (12)	0.0321 (12)	0.0011 (13)	0.0101 (11)	−0.0015 (11)
O3	0.076 (2)	0.168 (4)	0.0489 (19)	0.040 (3)	0.0199 (16)	−0.007 (2)
O4	0.113 (3)	0.086 (2)	0.0419 (17)	−0.015 (2)	0.0324 (17)	0.0032 (17)
N1	0.0571 (18)	0.0288 (16)	0.0259 (14)	0.0000 (15)	0.0105 (12)	−0.0017 (12)
N2	0.0492 (17)	0.0322 (15)	0.0274 (15)	0.0007 (14)	0.0087 (12)	−0.0020 (12)
N3	0.059 (2)	0.094 (3)	0.038 (2)	−0.011 (2)	0.0142 (17)	−0.008 (2)
C1	0.065 (3)	0.110 (4)	0.043 (2)	−0.008 (3)	0.023 (2)	−0.018 (2)
C2	0.0412 (19)	0.068 (3)	0.035 (2)	−0.014 (2)	0.0156 (15)	−0.0043 (19)
C3	0.092 (3)	0.069 (3)	0.031 (2)	0.011 (3)	−0.002 (2)	0.0080 (19)
C4	0.083 (3)	0.070 (3)	0.044 (2)	0.034 (3)	−0.001 (2)	0.002 (2)
C5	0.0385 (19)	0.049 (2)	0.0337 (18)	−0.0054 (19)	0.0090 (15)	−0.0003 (16)
C6	0.064 (2)	0.065 (3)	0.035 (2)	0.015 (2)	−0.0024 (18)	0.0006 (19)
C7	0.055 (2)	0.094 (4)	0.046 (2)	0.025 (3)	0.0002 (19)	−0.015 (2)
C8	0.048 (2)	0.056 (2)	0.037 (2)	−0.008 (2)	0.0126 (16)	−0.0022 (18)
C9	0.0385 (19)	0.042 (2)	0.0282 (17)	0.0001 (17)	0.0049 (14)	−0.0003 (15)
C10	0.0410 (19)	0.037 (2)	0.0396 (19)	−0.0052 (17)	0.0121 (16)	−0.0015 (16)
C11	0.0473 (19)	0.0326 (17)	0.0349 (19)	−0.0044 (17)	0.0051 (15)	−0.0069 (15)
C12	0.0395 (19)	0.0279 (17)	0.0259 (16)	0.0045 (16)	0.0035 (14)	−0.0016 (13)
C13	0.0467 (19)	0.039 (2)	0.0311 (17)	−0.0066 (18)	0.0073 (15)	−0.0001 (16)
C14	0.049 (2)	0.043 (2)	0.0333 (19)	−0.0072 (19)	0.0019 (15)	−0.0074 (16)
C15	0.0373 (19)	0.0297 (18)	0.0276 (16)	0.0041 (16)	0.0006 (14)	−0.0006 (14)
C16	0.061 (2)	0.0318 (18)	0.0320 (18)	−0.0014 (18)	0.0108 (16)	−0.0054 (15)
C17	0.056 (2)	0.036 (2)	0.0312 (18)	−0.0137 (18)	0.0114 (16)	−0.0051 (15)
C18	0.054 (2)	0.048 (2)	0.038 (2)	−0.008 (2)	0.0104 (17)	−0.0014 (17)
C19	0.051 (2)	0.057 (2)	0.047 (2)	−0.009 (2)	0.0170 (18)	−0.010 (2)
C20	0.051 (2)	0.068 (3)	0.0306 (19)	−0.019 (2)	0.0144 (16)	−0.007 (2)
C21	0.079 (3)	0.054 (3)	0.032 (2)	−0.018 (2)	0.0133 (19)	0.0022 (18)
C22	0.082 (3)	0.040 (2)	0.039 (2)	−0.006 (2)	0.021 (2)	0.0025 (17)

Geometric parameters (Å, º)

O1—C9	1.363 (4)	C8—H8A	0.9900
O1—C8	1.437 (4)	C8—H8B	0.9900
O2—C15	1.237 (4)	C9—C14	1.382 (5)
O3—N3	1.231 (6)	C9—C10	1.395 (5)
O4—N3	1.227 (5)	C10—C11	1.373 (4)
N1—C15	1.358 (4)	C10—H10	0.9500
N1—N2	1.376 (4)	C11—C12	1.395 (5)
N1—H1	0.90 (4)	C11—H11	0.9500
N2—C16	1.279 (4)	C12—C13	1.396 (5)
N3—C20	1.480 (5)	C12—C15	1.477 (4)
C1—C2	1.511 (5)	C13—C14	1.379 (5)
C1—H1A	0.9800	C13—H13	0.9500
C1—H1B	0.9800	C14—H14	0.9500
C1—H1C	0.9800	C16—C17	1.472 (5)
C2—C3	1.353 (6)	C16—H16	0.9500
C2—C7	1.386 (5)	C17—C18	1.385 (5)
C3—C4	1.379 (6)	C17—C22	1.398 (5)
C3—H3	0.9500	C18—C19	1.385 (5)
C4—C5	1.381 (5)	C18—H18	0.9500
C4—H4	0.9500	C19—C20	1.383 (6)
C5—C6	1.352 (6)	C19—H19	0.9500
C5—C8	1.500 (5)	C20—C21	1.360 (6)
C6—C7	1.377 (5)	C21—C22	1.374 (5)
C6—H6	0.9500	C21—H21	0.9500
C7—H7	0.9500	C22—H22	0.9500
C9—O1—C8	117.8 (3)	C14—C9—C10	119.3 (3)
C15—N1—N2	119.1 (3)	C11—C10—C9	119.5 (3)
C15—N1—H1	124 (2)	C11—C10—H10	120.2
N2—N1—H1	117 (2)	C9—C10—H10	120.2
C16—N2—N1	116.0 (3)	C10—C11—C12	121.9 (3)
O4—N3—O3	124.3 (4)	C10—C11—H11	119.1
O4—N3—C20	118.1 (4)	C12—C11—H11	119.1
O3—N3—C20	117.7 (4)	C11—C12—C13	117.9 (3)
C2—C1—H1A	109.5	C11—C12—C15	118.8 (3)
C2—C1—H1B	109.5	C13—C12—C15	123.3 (3)
H1A—C1—H1B	109.5	C14—C13—C12	120.4 (3)
C2—C1—H1C	109.5	C14—C13—H13	119.8
H1A—C1—H1C	109.5	C12—C13—H13	119.8
H1B—C1—H1C	109.5	C13—C14—C9	120.9 (3)
C3—C2—C7	117.0 (4)	C13—C14—H14	119.5
C3—C2—C1	121.6 (4)	C9—C14—H14	119.5
C7—C2—C1	121.4 (4)	O2—C15—N1	122.1 (3)
C2—C3—C4	121.8 (4)	O2—C15—C12	121.7 (3)
C2—C3—H3	119.1	N1—C15—C12	116.2 (3)
C4—C3—H3	119.1	N2—C16—C17	118.7 (3)
C3—C4—C5	120.9 (4)	N2—C16—H16	120.6
C3—C4—H4	119.5	C17—C16—H16	120.6
C5—C4—H4	119.5	C18—C17—C22	119.3 (3)
C6—C5—C4	117.6 (4)	C18—C17—C16	121.6 (3)
C6—C5—C8	121.1 (3)	C22—C17—C16	119.1 (3)
C4—C5—C8	121.2 (4)	C19—C18—C17	119.8 (4)
C5—C6—C7	121.3 (4)	C19—C18—H18	120.1
C5—C6—H6	119.3	C17—C18—H18	120.1
C7—C6—H6	119.3	C20—C19—C18	118.6 (4)
C6—C7—C2	121.4 (4)	C20—C19—H19	120.7
C6—C7—H7	119.3	C18—C19—H19	120.7
C2—C7—H7	119.3	C21—C20—C19	123.1 (3)
O1—C8—C5	108.1 (3)	C21—C20—N3	118.5 (4)
O1—C8—H8A	110.1	C19—C20—N3	118.4 (4)
C5—C8—H8A	110.1	C20—C21—C22	117.9 (4)
O1—C8—H8B	110.1	C20—C21—H21	121.1
C5—C8—H8B	110.1	C22—C21—H21	121.1
H8A—C8—H8B	108.4	C21—C22—C17	121.3 (4)
O1—C9—C14	115.7 (3)	C21—C22—H22	119.3
O1—C9—C10	125.0 (3)	C17—C22—H22	119.3
C15—N1—N2—C16	166.0 (3)	C10—C9—C14—C13	2.9 (5)
C7—C2—C3—C4	0.3 (7)	N2—N1—C15—O2	−5.3 (5)
C1—C2—C3—C4	−179.5 (5)	N2—N1—C15—C12	174.1 (3)
C2—C3—C4—C5	−0.5 (8)	C11—C12—C15—O2	−25.7 (5)
C3—C4—C5—C6	0.2 (7)	C13—C12—C15—O2	151.0 (3)
C3—C4—C5—C8	179.3 (4)	C11—C12—C15—N1	154.8 (3)
C4—C5—C6—C7	0.2 (6)	C13—C12—C15—N1	−28.5 (5)
C8—C5—C6—C7	−178.9 (4)	N1—N2—C16—C17	−179.9 (3)
C5—C6—C7—C2	−0.4 (7)	N2—C16—C17—C18	−27.8 (5)
C3—C2—C7—C6	0.2 (7)	N2—C16—C17—C22	149.9 (4)
C1—C2—C7—C6	179.9 (4)	C22—C17—C18—C19	−0.4 (5)
C9—O1—C8—C5	−170.9 (3)	C16—C17—C18—C19	177.2 (4)
C6—C5—C8—O1	80.9 (4)	C17—C18—C19—C20	−0.6 (5)
C4—C5—C8—O1	−98.2 (5)	C18—C19—C20—C21	0.5 (6)
C8—O1—C9—C14	177.9 (3)	C18—C19—C20—N3	179.1 (4)
C8—O1—C9—C10	−3.5 (5)	O4—N3—C20—C21	1.5 (5)
O1—C9—C10—C11	179.5 (3)	O3—N3—C20—C21	−177.5 (4)
C14—C9—C10—C11	−2.0 (5)	O4—N3—C20—C19	−177.2 (4)
C9—C10—C11—C12	0.0 (5)	O3—N3—C20—C19	3.9 (5)
C10—C11—C12—C13	1.1 (5)	C19—C20—C21—C22	0.7 (6)
C10—C11—C12—C15	177.9 (3)	N3—C20—C21—C22	−177.9 (3)
C11—C12—C13—C14	−0.2 (5)	C20—C21—C22—C17	−1.8 (6)
C15—C12—C13—C14	−176.9 (3)	C18—C17—C22—C21	1.7 (6)
C12—C13—C14—C9	−1.8 (5)	C16—C17—C22—C21	−176.0 (3)
O1—C9—C14—C13	−178.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···N2^i	0.95	2.68	3.524 (5)	148
C16—H16···O2^ii	0.95	2.45	3.259 (4)	143
C21—H21···O4^iii	0.95	2.59	3.532 (5)	171
N1—H1···O2^ii	0.90 (4)	2.04 (4)	2.911 (4)	161 (3)

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