(E)-1-(5-Bromo-2-eth­oxy-3-methoxy­benzyl­idene)-2-(2,4-dinitro­phen­yl)hydrazine dimethyl­formamide solvate

In the title compound, C₁₆H₁₅BrN₄O₆·C₃H₇NO, the substituted vanillin group makes a dihedral angle of 7.58 (10)° with the nitro­phenyl­hydrazine mean plane. A bifurcated intra/inter­molecular N—H...(O,O) hydrogen bond and two C—H...O inter­actions help to establish the mol­ecular conformation and consolidate the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.040
• wR factor = 0.104
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.82 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.22 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N3
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N5
PLAT432_ALERT_2_C Short Inter X...Y Contact  O5     ..  C7      ..       2.96 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   3 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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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)-1-(5-Bromo-2-ethoxy-3-methoxybenzylidene)-2-(2,4-dinitrophenyl)hydrazine dimethylformamide solvate

Crystal data

C16H15BrN4O6·C3H7NO	Z = 2
Mr = 512.33	F(000) = 524
Triclinic, P1	Dx = 1.498 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.521 (2) Å	Cell parameters from 1975 reflections
b = 11.698 (3) Å	θ = 2.5–24.4°
c = 13.135 (4) Å	µ = 1.86 mm^−1
α = 64.889 (4)°	T = 294 K
β = 73.484 (4)°	Block, orange
γ = 80.844 (5)°	0.30 × 0.20 × 0.16 mm
V = 1135.5 (5) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3952 independent reflections
Radiation source: fine-focus sealed tube	2660 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→9
Tmin = 0.605, Tmax = 0.743	k = −8→13
5768 measured reflections	l = −11→15

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)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.104	w = 1/[σ^2(Fo^2) + (0.0472P)^2 + 0.1537P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3952 reflections	Δρmax = 0.31 e Å^−3
294 parameters	Δρmin = −0.30 e Å^−3
72 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: 0.0242 (18)

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
Br1	0.13008 (6)	0.63286 (4)	0.50421 (3)	0.0684 (2)
O1	−0.2427 (3)	0.9830 (2)	0.62188 (18)	0.0491 (6)
O2	−0.1616 (3)	0.8987 (2)	0.82507 (17)	0.0424 (5)
O3	0.2047 (4)	0.6010 (3)	1.2171 (2)	0.0775 (9)
O4	0.3367 (5)	0.4689 (3)	1.3364 (3)	0.0987 (11)
O5	0.6288 (3)	0.1108 (3)	1.2890 (2)	0.0677 (8)
O6	0.6567 (4)	0.0853 (3)	1.1331 (3)	0.0982 (11)
N1	0.1531 (3)	0.5985 (3)	0.9286 (2)	0.0388 (6)
N2	0.1816 (3)	0.5656 (2)	1.0362 (2)	0.0409 (7)
H2	0.1354	0.6083	1.0771	0.049*
N3	0.2880 (4)	0.5046 (3)	1.2479 (2)	0.0553 (8)
N4	0.5989 (4)	0.1422 (3)	1.1942 (3)	0.0548 (8)
C1	0.0166 (4)	0.7364 (3)	0.7835 (2)	0.0357 (7)
C2	0.0819 (4)	0.6726 (3)	0.7106 (3)	0.0425 (8)
H2A	0.1530	0.6023	0.7320	0.051*
C3	0.0390 (4)	0.7157 (3)	0.6068 (3)	0.0423 (8)
C4	−0.0687 (4)	0.8186 (3)	0.5733 (3)	0.0410 (8)
H4	−0.0968	0.8447	0.5031	0.049*
C5	−0.1342 (4)	0.8821 (3)	0.6443 (2)	0.0378 (8)
C6	−0.0900 (4)	0.8408 (3)	0.7508 (2)	0.0350 (7)
C7	−0.2956 (4)	1.0231 (4)	0.5176 (3)	0.0540 (10)
H7A	−0.2023	1.0452	0.4524	0.081*
H7B	−0.3700	1.0955	0.5101	0.081*
H7C	−0.3499	0.9558	0.5200	0.081*
C8	−0.0968 (5)	1.0167 (4)	0.7980 (3)	0.0668 (11)
H8A	−0.1221	1.0804	0.7272	0.080*
H8B	0.0213	1.0076	0.7867	0.080*
C9	−0.1716 (7)	1.0549 (5)	0.8952 (4)	0.0989 (16)
H9A	−0.2881	1.0662	0.9041	0.148*
H9B	−0.1277	1.1328	0.8797	0.148*
H9C	−0.1480	0.9905	0.9651	0.148*
C10	0.0548 (4)	0.6934 (3)	0.8970 (2)	0.0384 (8)
H10	0.0072	0.7354	0.9453	0.046*
C11	0.2829 (4)	0.4652 (3)	1.0757 (2)	0.0353 (7)
C12	0.3348 (4)	0.4295 (3)	1.1794 (2)	0.0376 (8)
C13	0.4370 (4)	0.3251 (3)	1.2172 (3)	0.0407 (8)
H13	0.4689	0.3037	1.2853	0.049*
C14	0.4912 (4)	0.2529 (3)	1.1541 (3)	0.0406 (8)
C15	0.4459 (4)	0.2846 (3)	1.0506 (3)	0.0430 (8)
H15	0.4846	0.2356	1.0076	0.052*
C16	0.3450 (4)	0.3874 (3)	1.0138 (2)	0.0407 (8)
H16	0.3153	0.4077	0.9450	0.049*
O8	0.8769 (4)	0.6789 (3)	0.1491 (3)	0.0951 (10)
N5	0.6931 (4)	0.7280 (3)	0.2874 (3)	0.0674 (9)
C17	0.8365 (6)	0.6909 (4)	0.2398 (4)	0.0736 (12)
H17	0.9169	0.6713	0.2807	0.088*
C18	0.5662 (7)	0.7699 (6)	0.2256 (5)	0.122 (2)
H18A	0.6145	0.7946	0.1442	0.183*
H18B	0.5053	0.8408	0.2389	0.183*
H18C	0.4940	0.7024	0.2523	0.183*
C19	0.6584 (7)	0.7400 (6)	0.3960 (4)	0.121 (2)
H19A	0.7540	0.7139	0.4266	0.182*
H19B	0.5697	0.6876	0.4496	0.182*
H19C	0.6283	0.8265	0.3844	0.182*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0887 (4)	0.0723 (3)	0.0531 (3)	0.0123 (2)	−0.0164 (2)	−0.0394 (2)
O1	0.0496 (15)	0.0517 (15)	0.0434 (13)	0.0136 (12)	−0.0227 (11)	−0.0148 (11)
O2	0.0482 (14)	0.0414 (14)	0.0360 (11)	−0.0005 (11)	−0.0073 (10)	−0.0165 (10)
O3	0.109 (2)	0.069 (2)	0.0776 (19)	0.0346 (18)	−0.0510 (18)	−0.0463 (17)
O4	0.157 (3)	0.099 (2)	0.0711 (19)	0.041 (2)	−0.071 (2)	−0.0519 (18)
O5	0.0672 (18)	0.0764 (19)	0.0524 (15)	0.0129 (15)	−0.0306 (14)	−0.0146 (14)
O6	0.119 (3)	0.103 (2)	0.082 (2)	0.063 (2)	−0.0447 (19)	−0.056 (2)
N1	0.0431 (17)	0.0411 (17)	0.0284 (13)	−0.0029 (14)	−0.0135 (12)	−0.0069 (12)
N2	0.0473 (17)	0.0432 (17)	0.0310 (13)	0.0011 (14)	−0.0138 (12)	−0.0122 (12)
N3	0.075 (2)	0.055 (2)	0.0441 (17)	−0.0032 (18)	−0.0235 (16)	−0.0212 (16)
N4	0.0485 (19)	0.060 (2)	0.0486 (18)	0.0050 (16)	−0.0162 (15)	−0.0149 (17)
C1	0.0360 (19)	0.0363 (19)	0.0316 (16)	−0.0057 (15)	−0.0068 (14)	−0.0102 (15)
C2	0.047 (2)	0.040 (2)	0.0384 (18)	0.0017 (16)	−0.0107 (15)	−0.0144 (16)
C3	0.045 (2)	0.047 (2)	0.0353 (17)	−0.0040 (17)	−0.0041 (15)	−0.0194 (16)
C4	0.041 (2)	0.051 (2)	0.0301 (16)	−0.0050 (17)	−0.0102 (15)	−0.0132 (16)
C5	0.0356 (19)	0.039 (2)	0.0335 (17)	−0.0059 (16)	−0.0070 (14)	−0.0090 (15)
C6	0.0357 (19)	0.0382 (19)	0.0292 (16)	−0.0049 (15)	−0.0045 (14)	−0.0127 (14)
C7	0.047 (2)	0.066 (3)	0.0465 (19)	0.0064 (19)	−0.0243 (17)	−0.0144 (18)
C8	0.084 (3)	0.054 (3)	0.064 (2)	−0.010 (2)	−0.008 (2)	−0.030 (2)
C9	0.134 (4)	0.081 (3)	0.098 (3)	−0.004 (3)	−0.017 (3)	−0.059 (3)
C10	0.044 (2)	0.0373 (19)	0.0298 (16)	−0.0026 (16)	−0.0087 (15)	−0.0099 (15)
C11	0.0323 (18)	0.0377 (19)	0.0307 (16)	−0.0083 (15)	−0.0072 (14)	−0.0068 (15)
C12	0.043 (2)	0.039 (2)	0.0294 (16)	−0.0044 (16)	−0.0084 (14)	−0.0114 (15)
C13	0.041 (2)	0.047 (2)	0.0291 (16)	−0.0080 (17)	−0.0129 (15)	−0.0058 (16)
C14	0.0351 (19)	0.041 (2)	0.0374 (17)	−0.0014 (16)	−0.0096 (15)	−0.0081 (16)
C15	0.042 (2)	0.050 (2)	0.0344 (17)	0.0002 (17)	−0.0066 (15)	−0.0164 (16)
C16	0.044 (2)	0.046 (2)	0.0289 (16)	−0.0058 (17)	−0.0104 (15)	−0.0094 (15)
O8	0.105 (2)	0.127 (3)	0.0637 (18)	0.020 (2)	−0.0172 (17)	−0.0577 (19)
N5	0.071 (2)	0.081 (2)	0.0580 (19)	0.0132 (19)	−0.0193 (18)	−0.0382 (18)
C17	0.081 (3)	0.080 (3)	0.065 (3)	0.009 (2)	−0.021 (2)	−0.035 (2)
C18	0.101 (4)	0.163 (5)	0.125 (4)	0.010 (4)	−0.046 (4)	−0.072 (4)
C19	0.134 (5)	0.161 (5)	0.085 (3)	0.033 (4)	−0.028 (3)	−0.077 (4)

Geometric parameters (Å, º)

C3—Br1	1.905 (3)	C8—C9	1.471 (6)
O1—C5	1.359 (4)	C8—H8A	0.9700
O1—C7	1.428 (4)	C8—H8B	0.9700
O2—C6	1.368 (3)	C9—H9A	0.9600
O2—C8	1.432 (4)	C9—H9B	0.9600
O3—N3	1.209 (4)	C9—H9C	0.9600
O4—N3	1.226 (4)	C10—H10	0.9300
O5—N4	1.230 (3)	C11—C16	1.413 (4)
O6—N4	1.206 (4)	C11—C12	1.424 (4)
N1—C10	1.272 (4)	C12—C13	1.374 (4)
N1—N2	1.381 (3)	C13—C14	1.366 (4)
N2—C11	1.345 (4)	C13—H13	0.9300
N2—H2	0.8600	C14—C15	1.401 (4)
N3—C12	1.448 (4)	C15—C16	1.354 (4)
N4—C14	1.453 (4)	C15—H15	0.9300
C1—C6	1.388 (4)	C16—H16	0.9300
C1—C2	1.398 (4)	O8—C17	1.204 (4)
C1—C10	1.473 (4)	N5—C17	1.304 (5)
C2—C3	1.374 (4)	N5—C19	1.434 (5)
C2—H2A	0.9300	N5—C18	1.436 (6)
C3—C4	1.383 (4)	C17—H17	0.9300
C4—C5	1.377 (4)	C18—H18A	0.9600
C4—H4	0.9300	C18—H18B	0.9600
C5—C6	1.414 (4)	C18—H18C	0.9600
C7—H7A	0.9600	C19—H19A	0.9600
C7—H7B	0.9600	C19—H19B	0.9600
C7—H7C	0.9600	C19—H19C	0.9600
C5—O1—C7	116.8 (3)	H9A—C9—H9B	109.5
C6—O2—C8	116.1 (2)	C8—C9—H9C	109.5
C10—N1—N2	115.5 (3)	H9A—C9—H9C	109.5
C11—N2—N1	118.7 (3)	H9B—C9—H9C	109.5
C11—N2—H2	120.7	N1—C10—C1	119.7 (3)
N1—N2—H2	120.7	N1—C10—H10	120.1
O3—N3—O4	121.2 (3)	C1—C10—H10	120.1
O3—N3—C12	120.3 (3)	N2—C11—C16	120.4 (3)
O4—N3—C12	118.5 (3)	N2—C11—C12	123.9 (3)
O6—N4—O5	122.4 (3)	C16—C11—C12	115.7 (3)
O6—N4—C14	119.0 (3)	C13—C12—C11	121.9 (3)
O5—N4—C14	118.6 (3)	C13—C12—N3	116.5 (3)
C6—C1—C2	120.1 (3)	C11—C12—N3	121.6 (3)
C6—C1—C10	118.4 (3)	C14—C13—C12	119.6 (3)
C2—C1—C10	121.5 (3)	C14—C13—H13	120.2
C3—C2—C1	118.8 (3)	C12—C13—H13	120.2
C3—C2—H2A	120.6	C13—C14—C15	120.9 (3)
C1—C2—H2A	120.6	C13—C14—N4	119.7 (3)
C2—C3—C4	122.0 (3)	C15—C14—N4	119.4 (3)
C2—C3—Br1	119.7 (3)	C16—C15—C14	119.2 (3)
C4—C3—Br1	118.3 (2)	C16—C15—H15	120.4
C5—C4—C3	119.8 (3)	C14—C15—H15	120.4
C5—C4—H4	120.1	C15—C16—C11	122.6 (3)
C3—C4—H4	120.1	C15—C16—H16	118.7
O1—C5—C4	125.2 (3)	C11—C16—H16	118.7
O1—C5—C6	115.5 (3)	C17—N5—C19	122.9 (4)
C4—C5—C6	119.3 (3)	C17—N5—C18	119.7 (4)
O2—C6—C1	120.1 (2)	C19—N5—C18	117.1 (4)
O2—C6—C5	119.7 (3)	O8—C17—N5	127.5 (4)
C1—C6—C5	120.0 (3)	O8—C17—H17	116.2
O1—C7—H7A	109.5	N5—C17—H17	116.2
O1—C7—H7B	109.5	N5—C18—H18A	109.5
H7A—C7—H7B	109.5	N5—C18—H18B	109.5
O1—C7—H7C	109.5	H18A—C18—H18B	109.5
H7A—C7—H7C	109.5	N5—C18—H18C	109.5
H7B—C7—H7C	109.5	H18A—C18—H18C	109.5
O2—C8—C9	108.1 (3)	H18B—C18—H18C	109.5
O2—C8—H8A	110.1	N5—C19—H19A	109.5
C9—C8—H8A	110.1	N5—C19—H19B	109.5
O2—C8—H8B	110.1	H19A—C19—H19B	109.5
C9—C8—H8B	110.1	N5—C19—H19C	109.5
H8A—C8—H8B	108.4	H19A—C19—H19C	109.5
C8—C9—H9A	109.5	H19B—C19—H19C	109.5
C8—C9—H9B	109.5
C10—N1—N2—C11	179.3 (3)	N1—N2—C11—C16	−6.6 (4)
C6—C1—C2—C3	0.3 (4)	N1—N2—C11—C12	173.5 (3)
C10—C1—C2—C3	178.6 (3)	N2—C11—C12—C13	179.1 (3)
C1—C2—C3—C4	−1.2 (5)	C16—C11—C12—C13	−0.8 (4)
C1—C2—C3—Br1	178.6 (2)	N2—C11—C12—N3	−3.5 (5)
C2—C3—C4—C5	1.0 (5)	C16—C11—C12—N3	176.6 (3)
Br1—C3—C4—C5	−178.7 (2)	O3—N3—C12—C13	176.5 (3)
C7—O1—C5—C4	1.8 (4)	O4—N3—C12—C13	−2.4 (5)
C7—O1—C5—C6	−177.1 (3)	O3—N3—C12—C11	−1.0 (5)
C3—C4—C5—O1	−179.0 (3)	O4—N3—C12—C11	−179.9 (3)
C3—C4—C5—C6	0.0 (4)	C11—C12—C13—C14	0.1 (5)
C8—O2—C6—C1	104.9 (3)	N3—C12—C13—C14	−177.4 (3)
C8—O2—C6—C5	−79.7 (4)	C12—C13—C14—C15	0.8 (5)
C2—C1—C6—O2	176.1 (3)	C12—C13—C14—N4	−179.8 (3)
C10—C1—C6—O2	−2.3 (4)	O6—N4—C14—C13	−174.0 (3)
C2—C1—C6—C5	0.6 (4)	O5—N4—C14—C13	5.4 (5)
C10—C1—C6—C5	−177.7 (3)	O6—N4—C14—C15	5.4 (5)
O1—C5—C6—O2	2.8 (4)	O5—N4—C14—C15	−175.2 (3)
C4—C5—C6—O2	−176.2 (3)	C13—C14—C15—C16	−0.9 (5)
O1—C5—C6—C1	178.2 (3)	N4—C14—C15—C16	179.7 (3)
C4—C5—C6—C1	−0.8 (4)	C14—C15—C16—C11	0.1 (5)
C6—O2—C8—C9	−172.0 (3)	N2—C11—C16—C15	−179.2 (3)
N2—N1—C10—C1	179.8 (2)	C12—C11—C16—C15	0.7 (4)
C6—C1—C10—N1	−179.5 (3)	C19—N5—C17—O8	−179.4 (5)
C2—C1—C10—N1	2.2 (4)	C18—N5—C17—O8	−5.2 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O8^i	0.86	2.31	3.014 (4)	139
N2—H2···O3	0.86	2.05	2.643 (3)	125
C10—H10···O8^i	0.93	2.42	3.170 (4)	137
C17—H17···O3^ii	0.93	2.48	3.118 (6)	126

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