(E)-2-Meth­oxy-N′-{2-[2-(2-nitro­phen­oxy)­ethoxy]benzyl­idene}benzohydrazide

In the title compound, C₂₃H₂₁N₃O₆, the salicylaldehyde group makes dihedral angles of 53.06 (12) and 16.36 (10)° with the terminal nitro­benzene ring and the benzohydrazide group, respectively. An intra­molecular N—H...O hydrogen bond helps to stabilize the mol­ecular conformation, while weak inter­molecular C—H...O hydrogen bonds link adjacent mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.059
• wR factor = 0.174
• Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

(E)-2-Methoxy-N'-{2-[2-(2-nitrophenoxy)ethoxy]benzylidene}benzohydrazide

Crystal data

C23H21N3O6	F(000) = 912
Mr = 435.43	Dx = 1.367 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1728 reflections
a = 7.6079 (16) Å	θ = 2.5–21.6°
b = 13.050 (3) Å	µ = 0.10 mm^−1
c = 21.318 (4) Å	T = 294 K
β = 90.628 (4)°	Block, colorless
V = 2116.4 (8) Å^3	0.22 × 0.20 × 0.16 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3714 independent reflections
Radiation source: fine-focus sealed tube	1891 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→6
Tmin = 0.952, Tmax = 0.984	k = −14→15
10532 measured reflections	l = −24→25

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.059	H-atom parameters constrained
wR(F^2) = 0.174	w = 1/[σ^2(Fo^2) + (0.0628P)^2 + 1.0365P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.002
3714 reflections	Δρmax = 0.18 e Å^−3
291 parameters	Δρmin = −0.17 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0058 (11)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.8498 (5)	0.5397 (3)	0.41658 (19)	0.1105 (14)
O2	0.6893 (4)	0.6045 (2)	0.34447 (18)	0.0916 (11)
O3	0.3938 (3)	0.62773 (19)	0.41787 (12)	0.0606 (8)
O4	0.2935 (4)	0.79254 (19)	0.34808 (11)	0.0662 (8)
O5	0.6221 (4)	0.6980 (2)	0.06821 (12)	0.0779 (10)
O6	0.5948 (4)	0.46853 (18)	0.20282 (11)	0.0608 (8)
N1	0.7118 (5)	0.5474 (3)	0.3890 (2)	0.0659 (10)
N2	0.5219 (4)	0.7617 (2)	0.18359 (14)	0.0550 (9)
N3	0.5617 (4)	0.6615 (2)	0.16889 (14)	0.0545 (9)
H3	0.5527	0.6148	0.1971	0.065*
C1	0.5673 (5)	0.4815 (3)	0.40765 (16)	0.0496 (10)
C2	0.5994 (6)	0.3778 (3)	0.41157 (16)	0.0615 (11)
H2	0.7121	0.3520	0.4059	0.074*
C3	0.4625 (7)	0.3139 (3)	0.42397 (19)	0.0733 (13)
H3A	0.4811	0.2436	0.4264	0.088*
C4	0.2961 (7)	0.3534 (4)	0.4330 (2)	0.0782 (14)
H4	0.2028	0.3090	0.4402	0.094*
C5	0.2662 (5)	0.4578 (3)	0.43161 (17)	0.0635 (11)
H5	0.1543	0.4835	0.4391	0.076*
C6	0.4040 (5)	0.5242 (3)	0.41903 (16)	0.0493 (10)
C7	0.2272 (5)	0.6761 (3)	0.42673 (18)	0.0590 (11)
H7A	0.1884	0.6669	0.4696	0.071*
H7B	0.1395	0.6469	0.3986	0.071*
C8	0.2528 (5)	0.7866 (3)	0.41288 (16)	0.0561 (10)
H8A	0.1466	0.8249	0.4217	0.067*
H8B	0.3482	0.8143	0.4382	0.067*
C9	0.3440 (5)	0.8835 (3)	0.32262 (17)	0.0486 (9)
C10	0.3195 (5)	0.9775 (3)	0.34952 (19)	0.0624 (11)
H10	0.2723	0.9825	0.3894	0.075*
C11	0.3650 (6)	1.0645 (3)	0.3174 (2)	0.0736 (13)
H11	0.3472	1.1283	0.3357	0.088*
C12	0.4362 (6)	1.0589 (3)	0.2589 (2)	0.0741 (13)
H12	0.4667	1.1182	0.2375	0.089*
C13	0.4621 (5)	0.9641 (3)	0.23195 (19)	0.0615 (11)
H13	0.5092	0.9602	0.1919	0.074*
C14	0.4197 (5)	0.8751 (3)	0.26310 (17)	0.0480 (9)
C15	0.4574 (5)	0.7739 (3)	0.23792 (17)	0.0526 (10)
H15	0.4337	0.7165	0.2622	0.063*
C16	0.6147 (5)	0.6358 (3)	0.11064 (18)	0.0523 (10)
C17	0.6633 (5)	0.5253 (3)	0.10089 (16)	0.0467 (9)
C18	0.7226 (6)	0.5005 (3)	0.04193 (18)	0.0683 (13)
H18	0.7285	0.5522	0.0120	0.082*
C19	0.7728 (7)	0.4047 (3)	0.0254 (2)	0.0786 (15)
H19	0.8111	0.3913	−0.0151	0.094*
C20	0.7662 (6)	0.3288 (3)	0.0687 (2)	0.0673 (12)
H20	0.8008	0.2628	0.0579	0.081*
C21	0.7093 (5)	0.3480 (3)	0.12827 (17)	0.0547 (10)
H21	0.7057	0.2955	0.1577	0.066*
C22	0.6570 (5)	0.4464 (3)	0.14441 (16)	0.0462 (9)
C23	0.5653 (6)	0.3876 (3)	0.24690 (17)	0.0650 (12)
H23A	0.4872	0.3379	0.2286	0.097*
H23B	0.5138	0.4153	0.2842	0.097*
H23C	0.6752	0.3555	0.2574	0.097*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.047 (2)	0.149 (4)	0.135 (3)	−0.016 (2)	−0.002 (2)	−0.028 (3)
O2	0.086 (3)	0.062 (2)	0.127 (3)	−0.0060 (18)	0.039 (2)	0.015 (2)
O3	0.0440 (16)	0.0529 (17)	0.085 (2)	−0.0014 (13)	0.0102 (14)	0.0007 (14)
O4	0.098 (2)	0.0527 (17)	0.0485 (16)	−0.0018 (16)	0.0150 (15)	−0.0056 (13)
O5	0.133 (3)	0.0446 (16)	0.0567 (17)	0.0003 (17)	0.0244 (17)	0.0035 (14)
O6	0.085 (2)	0.0486 (15)	0.0491 (16)	0.0052 (14)	0.0081 (14)	0.0023 (13)
N1	0.055 (3)	0.057 (2)	0.086 (3)	−0.003 (2)	0.020 (2)	−0.019 (2)
N2	0.068 (2)	0.0383 (18)	0.059 (2)	0.0004 (16)	0.0096 (18)	−0.0035 (15)
N3	0.077 (2)	0.0345 (17)	0.0524 (19)	0.0022 (16)	0.0145 (17)	−0.0049 (14)
C1	0.052 (3)	0.048 (2)	0.049 (2)	−0.007 (2)	−0.0010 (19)	−0.0013 (18)
C2	0.076 (3)	0.055 (3)	0.053 (2)	0.003 (2)	−0.006 (2)	0.001 (2)
C3	0.100 (4)	0.055 (3)	0.065 (3)	−0.011 (3)	−0.007 (3)	0.010 (2)
C4	0.088 (4)	0.071 (3)	0.075 (3)	−0.034 (3)	−0.008 (3)	0.025 (2)
C5	0.052 (3)	0.074 (3)	0.065 (3)	−0.013 (2)	−0.001 (2)	0.020 (2)
C6	0.046 (2)	0.054 (3)	0.048 (2)	−0.008 (2)	−0.0020 (18)	0.0055 (18)
C7	0.044 (2)	0.077 (3)	0.056 (2)	0.004 (2)	0.0082 (19)	0.001 (2)
C8	0.055 (2)	0.071 (3)	0.043 (2)	0.011 (2)	0.0065 (19)	−0.006 (2)
C9	0.049 (2)	0.043 (2)	0.054 (2)	0.0026 (19)	−0.0010 (19)	−0.0072 (19)
C10	0.070 (3)	0.056 (3)	0.062 (3)	0.010 (2)	0.001 (2)	−0.013 (2)
C11	0.089 (4)	0.045 (3)	0.087 (3)	0.011 (2)	−0.004 (3)	−0.018 (2)
C12	0.091 (4)	0.046 (3)	0.085 (3)	−0.002 (2)	0.002 (3)	−0.002 (2)
C13	0.069 (3)	0.048 (2)	0.067 (3)	0.004 (2)	0.008 (2)	0.001 (2)
C14	0.048 (2)	0.038 (2)	0.058 (2)	0.0016 (18)	−0.0002 (19)	−0.0039 (18)
C15	0.060 (3)	0.044 (2)	0.054 (2)	0.0008 (19)	0.011 (2)	−0.0016 (18)
C16	0.063 (3)	0.043 (2)	0.052 (2)	−0.003 (2)	0.012 (2)	−0.004 (2)
C17	0.053 (2)	0.039 (2)	0.049 (2)	−0.0022 (18)	0.0063 (18)	−0.0014 (17)
C18	0.103 (4)	0.051 (3)	0.052 (2)	0.010 (2)	0.019 (2)	0.001 (2)
C19	0.124 (4)	0.056 (3)	0.056 (3)	0.020 (3)	0.025 (3)	−0.006 (2)
C20	0.084 (3)	0.049 (2)	0.069 (3)	0.015 (2)	0.005 (2)	−0.015 (2)
C21	0.065 (3)	0.043 (2)	0.056 (2)	0.010 (2)	−0.001 (2)	0.0015 (19)
C22	0.046 (2)	0.046 (2)	0.046 (2)	0.0016 (18)	−0.0006 (18)	−0.0058 (18)
C23	0.075 (3)	0.068 (3)	0.052 (2)	0.004 (2)	0.002 (2)	0.019 (2)

Geometric parameters (Å, º)

O1—N1	1.202 (5)	C8—H8B	0.9700
O2—N1	1.218 (4)	C9—C10	1.367 (5)
O3—C6	1.353 (4)	C9—C14	1.403 (5)
O3—C7	1.430 (4)	C10—C11	1.372 (5)
O4—C9	1.363 (4)	C10—H10	0.9300
O4—C8	1.421 (4)	C11—C12	1.367 (6)
O5—C16	1.217 (4)	C11—H11	0.9300
O6—C22	1.368 (4)	C12—C13	1.378 (5)
O6—C23	1.433 (4)	C12—H12	0.9300
N1—C1	1.454 (5)	C13—C14	1.378 (5)
N2—C15	1.273 (4)	C13—H13	0.9300
N2—N3	1.379 (4)	C14—C15	1.455 (5)
N3—C16	1.352 (4)	C15—H15	0.9300
N3—H3	0.8600	C16—C17	1.503 (5)
C1—C2	1.377 (5)	C17—C18	1.379 (5)
C1—C6	1.386 (5)	C17—C22	1.388 (5)
C2—C3	1.362 (6)	C18—C19	1.355 (5)
C2—H2	0.9300	C18—H18	0.9300
C3—C4	1.382 (6)	C19—C20	1.357 (5)
C3—H3A	0.9300	C19—H19	0.9300
C4—C5	1.382 (6)	C20—C21	1.368 (5)
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.389 (5)	C21—C22	1.389 (5)
C5—H5	0.9300	C21—H21	0.9300
C7—C8	1.486 (5)	C23—H23A	0.9600
C7—H7A	0.9700	C23—H23B	0.9600
C7—H7B	0.9700	C23—H23C	0.9600
C8—H8A	0.9700
C6—O3—C7	119.2 (3)	C9—C10—H10	120.1
C9—O4—C8	120.0 (3)	C11—C10—H10	120.1
C22—O6—C23	120.0 (3)	C12—C11—C10	121.0 (4)
O1—N1—O2	123.1 (4)	C12—C11—H11	119.5
O1—N1—C1	118.5 (4)	C10—C11—H11	119.5
O2—N1—C1	118.4 (4)	C11—C12—C13	119.3 (4)
C15—N2—N3	114.4 (3)	C11—C12—H12	120.4
C16—N3—N2	120.9 (3)	C13—C12—H12	120.4
C16—N3—H3	119.6	C14—C13—C12	121.3 (4)
N2—N3—H3	119.6	C14—C13—H13	119.3
C2—C1—C6	123.0 (4)	C12—C13—H13	119.3
C2—C1—N1	117.6 (4)	C13—C14—C9	118.0 (3)
C6—C1—N1	119.4 (3)	C13—C14—C15	122.6 (3)
C3—C2—C1	118.5 (4)	C9—C14—C15	119.3 (3)
C3—C2—H2	120.7	N2—C15—C14	121.9 (3)
C1—C2—H2	120.7	N2—C15—H15	119.0
C2—C3—C4	120.2 (4)	C14—C15—H15	119.0
C2—C3—H3A	119.9	O5—C16—N3	122.2 (3)
C4—C3—H3A	119.9	O5—C16—C17	121.6 (3)
C5—C4—C3	121.0 (4)	N3—C16—C17	116.2 (3)
C5—C4—H4	119.5	C18—C17—C22	116.7 (3)
C3—C4—H4	119.5	C18—C17—C16	115.8 (3)
C4—C5—C6	119.7 (4)	C22—C17—C16	127.5 (3)
C4—C5—H5	120.2	C19—C18—C17	123.4 (4)
C6—C5—H5	120.2	C19—C18—H18	118.3
O3—C6—C1	116.8 (3)	C17—C18—H18	118.3
O3—C6—C5	125.7 (4)	C18—C19—C20	118.9 (4)
C1—C6—C5	117.6 (4)	C18—C19—H19	120.5
O3—C7—C8	106.5 (3)	C20—C19—H19	120.5
O3—C7—H7A	110.4	C19—C20—C21	120.8 (4)
C8—C7—H7A	110.4	C19—C20—H20	119.6
O3—C7—H7B	110.4	C21—C20—H20	119.6
C8—C7—H7B	110.4	C20—C21—C22	119.6 (4)
H7A—C7—H7B	108.6	C20—C21—H21	120.2
O4—C8—C7	106.1 (3)	C22—C21—H21	120.2
O4—C8—H8A	110.5	O6—C22—C17	117.8 (3)
C7—C8—H8A	110.5	O6—C22—C21	121.6 (3)
O4—C8—H8B	110.5	C17—C22—C21	120.6 (3)
C7—C8—H8B	110.5	O6—C23—H23A	109.5
H8A—C8—H8B	108.7	O6—C23—H23B	109.5
O4—C9—C10	125.1 (4)	H23A—C23—H23B	109.5
O4—C9—C14	114.3 (3)	O6—C23—H23C	109.5
C10—C9—C14	120.6 (4)	H23A—C23—H23C	109.5
C9—C10—C11	119.8 (4)	H23B—C23—H23C	109.5
C15—N2—N3—C16	173.4 (4)	C12—C13—C14—C9	1.9 (6)
O1—N1—C1—C2	−51.4 (5)	C12—C13—C14—C15	−175.3 (4)
O2—N1—C1—C2	125.4 (4)	O4—C9—C14—C13	175.1 (3)
O1—N1—C1—C6	130.2 (4)	C10—C9—C14—C13	−2.4 (5)
O2—N1—C1—C6	−53.0 (5)	O4—C9—C14—C15	−7.6 (5)
C6—C1—C2—C3	3.5 (6)	C10—C9—C14—C15	174.9 (4)
N1—C1—C2—C3	−174.8 (4)	N3—N2—C15—C14	175.4 (3)
C1—C2—C3—C4	−0.7 (6)	C13—C14—C15—N2	−4.6 (6)
C2—C3—C4—C5	−2.0 (7)	C9—C14—C15—N2	178.2 (4)
C3—C4—C5—C6	2.0 (6)	N2—N3—C16—O5	−3.4 (6)
C7—O3—C6—C1	177.5 (3)	N2—N3—C16—C17	177.0 (3)
C7—O3—C6—C5	−3.7 (5)	O5—C16—C17—C18	2.4 (6)
C2—C1—C6—O3	175.5 (3)	N3—C16—C17—C18	−178.0 (4)
N1—C1—C6—O3	−6.2 (5)	O5—C16—C17—C22	−178.4 (4)
C2—C1—C6—C5	−3.5 (5)	N3—C16—C17—C22	1.2 (6)
N1—C1—C6—C5	174.8 (3)	C22—C17—C18—C19	0.3 (6)
C4—C5—C6—O3	−178.2 (4)	C16—C17—C18—C19	179.6 (4)
C4—C5—C6—C1	0.7 (6)	C17—C18—C19—C20	−0.5 (8)
C6—O3—C7—C8	−171.1 (3)	C18—C19—C20—C21	0.2 (7)
C9—O4—C8—C7	−172.5 (3)	C19—C20—C21—C22	0.3 (7)
O3—C7—C8—O4	65.2 (4)	C23—O6—C22—C17	172.3 (3)
C8—O4—C9—C10	−17.0 (5)	C23—O6—C22—C21	−6.4 (5)
C8—O4—C9—C14	165.7 (3)	C18—C17—C22—O6	−178.5 (3)
O4—C9—C10—C11	−175.5 (4)	C16—C17—C22—O6	2.3 (6)
C14—C9—C10—C11	1.7 (6)	C18—C17—C22—C21	0.2 (6)
C9—C10—C11—C12	−0.6 (7)	C16—C17—C22—C21	−179.0 (4)
C10—C11—C12—C13	0.1 (7)	C20—C21—C22—O6	178.2 (4)
C11—C12—C13—C14	−0.8 (7)	C20—C21—C22—C17	−0.5 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O6	0.86	1.94	2.632 (4)	137
C2—H2···O5^i	0.93	2.43	3.188 (5)	138
C5—H5···O1^ii	0.93	2.47	3.355 (6)	159

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