(E)-1-[2-(Benz­yloxy)-3-methoxy­benzyl­idene]-2-(2,4-dinitro­phen­yl)hydrazine dimethyl­formamide solvate

In the title compound, C₂₁H₁₈N₄O₆·C₃H₇NO, the substituted o-vanillin group makes dihedral angles of 37.17 (11) and 5.68 (8)°, respectively, with the phenyl ring and the phenyl­hydrazine mean plane. The packing is stabilized by an intra­molecular N—H...O hydrogen bond and a weak non-classical intermolecular C—H...O hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.051
• wR factor = 0.140
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.88 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N4     -   C21     ..       5.03 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1     -   C2      ..       5.12 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C4     -   C5      ..       5.90 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C6
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N5
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 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
   5 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
   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)-1-[2-(Benzyloxy)-3-methoxybenzylidene]-2-(2,4-dinitrophenyl)hydrazine dimethylformamide monosolvate

Crystal data

C21H18N4O6·C3H7NO	Z = 2
Mr = 495.49	F(000) = 520
Triclinic, P1	Dx = 1.330 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.244 (3) Å	Cell parameters from 1391 reflections
b = 11.792 (4) Å	θ = 2.4–25.6°
c = 12.789 (4) Å	µ = 0.10 mm^−1
α = 86.261 (7)°	T = 294 K
β = 87.312 (6)°	Block, red
γ = 86.856 (6)°	0.25 × 0.20 × 0.12 mm
V = 1237.6 (7) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	4290 independent reflections
Radiation source: fine-focus sealed tube	2133 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.949, Tmax = 0.988	k = −9→14
6206 measured reflections	l = −11→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.140	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0526P)^2 + 0.1421P] where P = (Fo^2 + 2Fc^2)/3
4290 reflections	(Δ/σ)max = 0.003
328 parameters	Δρmax = 0.15 e Å^−3
36 restraints	Δρmin = −0.17 e Å^−3

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	0.3903 (2)	0.21837 (16)	0.20490 (14)	0.0568 (6)
O2	0.2481 (3)	0.1414 (2)	0.04291 (16)	0.0766 (7)
O3	1.0887 (4)	−0.3086 (2)	0.7731 (2)	0.1069 (10)
O4	1.1415 (3)	−0.1625 (2)	0.85593 (19)	0.0819 (7)
O5	1.0137 (3)	0.20675 (19)	0.7038 (2)	0.0892 (8)
O6	0.8363 (3)	0.23962 (17)	0.58547 (17)	0.0679 (6)
N1	0.6512 (3)	0.01540 (19)	0.41265 (17)	0.0448 (6)
N2	0.7224 (3)	0.06945 (19)	0.48985 (16)	0.0443 (6)
H2	0.7117	0.1422	0.4924	0.053*
N3	1.0780 (3)	−0.2063 (3)	0.7850 (2)	0.0659 (8)
N4	0.9180 (3)	0.1730 (2)	0.6438 (2)	0.0558 (7)
C1	0.3127 (5)	0.4605 (3)	0.2073 (3)	0.0805 (11)
H1	0.3493	0.4313	0.2718	0.097*
C2	0.2154 (6)	0.5594 (4)	0.2025 (4)	0.1126 (15)
H2A	0.1869	0.5970	0.2629	0.135*
C3	0.1623 (6)	0.6007 (4)	0.1088 (6)	0.1172 (17)
H3	0.0968	0.6675	0.1056	0.141*
C4	0.2009 (6)	0.5483 (5)	0.0187 (5)	0.1144 (16)
H4	0.1625	0.5787	−0.0449	0.137*
C5	0.3006 (4)	0.4465 (3)	0.0234 (3)	0.0818 (11)
H5	0.3277	0.4087	−0.0371	0.098*
C6	0.3567 (4)	0.4042 (2)	0.1185 (2)	0.0526 (8)
C7	0.4637 (4)	0.2970 (3)	0.1267 (2)	0.0596 (8)
H7A	0.4744	0.2633	0.0594	0.072*
H7B	0.5711	0.3140	0.1471	0.072*
C8	0.4083 (3)	0.1046 (2)	0.1877 (2)	0.0446 (7)
C9	0.3304 (3)	0.0601 (3)	0.1055 (2)	0.0535 (8)
C10	0.3365 (4)	−0.0556 (3)	0.0948 (2)	0.0606 (9)
H10	0.2851	−0.0851	0.0401	0.073*
C11	0.4201 (4)	−0.1280 (3)	0.1664 (3)	0.0621 (9)
H11	0.4237	−0.2061	0.1594	0.075*
C12	0.4976 (4)	−0.0859 (2)	0.2477 (2)	0.0526 (8)
H12	0.5531	−0.1356	0.2947	0.063*
C13	0.4935 (3)	0.0317 (2)	0.2599 (2)	0.0422 (7)
C14	0.1738 (4)	0.1077 (4)	−0.0480 (3)	0.0865 (12)
H14A	0.2503	0.0611	−0.0873	0.130*
H14B	0.1408	0.1741	−0.0908	0.130*
H14C	0.0804	0.0653	−0.0269	0.130*
C15	0.5719 (3)	0.0805 (2)	0.3459 (2)	0.0432 (7)
H15	0.5644	0.1588	0.3523	0.052*
C16	0.8101 (3)	0.0051 (2)	0.5622 (2)	0.0406 (7)
C17	0.8145 (3)	−0.1157 (2)	0.5619 (2)	0.0459 (7)
H17	0.7577	−0.1494	0.5122	0.055*
C18	0.9005 (3)	−0.1834 (2)	0.6334 (2)	0.0493 (7)
H18	0.9019	−0.2621	0.6317	0.059*
C19	0.9857 (3)	−0.1340 (2)	0.7084 (2)	0.0466 (7)
C20	0.9885 (3)	−0.0189 (2)	0.7114 (2)	0.0463 (7)
H20	1.0470	0.0127	0.7617	0.056*
C21	0.9026 (3)	0.0516 (2)	0.6384 (2)	0.0423 (7)
O7	0.4956 (4)	0.3131 (3)	0.4836 (3)	0.1249 (12)
N5	0.3316 (4)	0.4097 (3)	0.5993 (3)	0.0783 (9)
C22	0.4651 (6)	0.3479 (3)	0.5681 (4)	0.0924 (12)
H22	0.5424	0.3304	0.6182	0.111*
C23	0.3054 (6)	0.4395 (5)	0.7071 (4)	0.1401 (19)
H23A	0.4011	0.4179	0.7452	0.210*
H23B	0.2148	0.4003	0.7388	0.210*
H23C	0.2831	0.5201	0.7089	0.210*
C24	0.2087 (6)	0.4441 (4)	0.5287 (4)	0.1333 (18)
H24A	0.2462	0.4281	0.4587	0.200*
H24B	0.1836	0.5243	0.5318	0.200*
H24C	0.1129	0.4033	0.5476	0.200*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0766 (15)	0.0488 (12)	0.0426 (12)	0.0082 (11)	0.0009 (10)	0.0036 (9)
O2	0.0776 (17)	0.0942 (17)	0.0578 (14)	0.0153 (13)	−0.0248 (12)	−0.0057 (13)
O3	0.143 (3)	0.0620 (17)	0.115 (2)	0.0278 (17)	−0.0510 (18)	0.0051 (16)
O4	0.0861 (18)	0.0888 (18)	0.0705 (17)	0.0110 (14)	−0.0319 (14)	0.0038 (14)
O5	0.104 (2)	0.0621 (15)	0.107 (2)	−0.0018 (13)	−0.0516 (17)	−0.0222 (14)
O6	0.0850 (17)	0.0442 (12)	0.0750 (15)	0.0066 (11)	−0.0192 (13)	−0.0033 (11)
N1	0.0445 (14)	0.0477 (14)	0.0416 (14)	0.0024 (11)	−0.0016 (11)	−0.0034 (12)
N2	0.0468 (15)	0.0436 (13)	0.0424 (14)	0.0006 (11)	−0.0046 (11)	−0.0015 (11)
N3	0.0636 (19)	0.065 (2)	0.067 (2)	0.0154 (15)	−0.0131 (15)	0.0057 (16)
N4	0.0598 (18)	0.0524 (16)	0.0553 (17)	0.0056 (14)	−0.0057 (14)	−0.0083 (14)
C1	0.098 (3)	0.056 (2)	0.087 (3)	0.013 (2)	−0.012 (2)	−0.007 (2)
C2	0.127 (4)	0.077 (3)	0.134 (4)	0.013 (3)	−0.001 (3)	−0.025 (3)
C3	0.099 (3)	0.071 (3)	0.177 (5)	0.010 (2)	−0.012 (4)	0.024 (3)
C4	0.098 (3)	0.114 (4)	0.125 (4)	−0.012 (3)	−0.038 (3)	0.064 (3)
C5	0.087 (3)	0.090 (3)	0.067 (2)	−0.002 (2)	−0.018 (2)	0.019 (2)
C6	0.0520 (19)	0.0479 (18)	0.057 (2)	−0.0057 (14)	−0.0058 (15)	0.0071 (16)
C7	0.059 (2)	0.058 (2)	0.059 (2)	−0.0027 (16)	−0.0008 (16)	0.0081 (16)
C8	0.0492 (18)	0.0468 (18)	0.0373 (17)	0.0014 (14)	0.0026 (14)	−0.0044 (14)
C9	0.0452 (19)	0.072 (2)	0.0424 (18)	0.0068 (16)	−0.0017 (15)	−0.0065 (17)
C10	0.055 (2)	0.076 (2)	0.054 (2)	−0.0072 (18)	−0.0020 (16)	−0.0211 (18)
C11	0.068 (2)	0.0490 (19)	0.070 (2)	−0.0032 (17)	0.0029 (19)	−0.0121 (17)
C12	0.058 (2)	0.0491 (19)	0.0504 (19)	0.0034 (15)	−0.0028 (15)	−0.0031 (15)
C13	0.0439 (17)	0.0474 (18)	0.0347 (16)	−0.0020 (14)	0.0067 (13)	−0.0039 (13)
C14	0.066 (2)	0.137 (4)	0.058 (2)	−0.009 (2)	−0.0175 (19)	−0.001 (2)
C15	0.0435 (18)	0.0456 (17)	0.0401 (17)	−0.0017 (14)	0.0008 (14)	−0.0031 (14)
C16	0.0359 (16)	0.0464 (17)	0.0382 (16)	0.0035 (13)	0.0034 (13)	−0.0004 (13)
C17	0.0466 (18)	0.0464 (17)	0.0447 (17)	0.0020 (14)	−0.0018 (14)	−0.0060 (14)
C18	0.0503 (19)	0.0423 (17)	0.0537 (19)	0.0056 (14)	0.0028 (15)	−0.0003 (14)
C19	0.0410 (17)	0.0532 (19)	0.0435 (18)	0.0070 (14)	−0.0011 (14)	0.0045 (14)
C20	0.0372 (17)	0.060 (2)	0.0410 (17)	−0.0003 (14)	−0.0007 (13)	−0.0044 (15)
C21	0.0430 (17)	0.0411 (16)	0.0425 (17)	0.0016 (13)	0.0018 (14)	−0.0057 (13)
O7	0.146 (3)	0.115 (2)	0.119 (2)	−0.001 (2)	0.000 (2)	−0.057 (2)
N5	0.077 (2)	0.072 (2)	0.087 (2)	0.0004 (17)	−0.0116 (18)	−0.0084 (17)
C22	0.102 (4)	0.072 (3)	0.104 (4)	0.000 (2)	−0.008 (3)	−0.019 (2)
C23	0.122 (4)	0.176 (5)	0.127 (4)	0.000 (3)	0.000 (3)	−0.057 (4)
C24	0.119 (4)	0.132 (4)	0.149 (4)	0.006 (3)	−0.051 (3)	0.010 (3)

Geometric parameters (Å, º)

O1—C8	1.373 (3)	C10—C11	1.392 (4)
O1—C7	1.453 (3)	C10—H10	0.9300
O2—C9	1.378 (3)	C11—C12	1.379 (4)
O2—C14	1.427 (4)	C11—H11	0.9300
O3—N3	1.224 (3)	C12—C13	1.404 (4)
O4—N3	1.225 (3)	C12—H12	0.9300
O5—N4	1.226 (3)	C13—C15	1.466 (3)
O6—N4	1.241 (3)	C14—H14A	0.9600
N1—C15	1.287 (3)	C14—H14B	0.9600
N1—N2	1.379 (3)	C14—H14C	0.9600
N2—C16	1.365 (3)	C15—H15	0.9300
N2—H2	0.8600	C16—C21	1.420 (4)
N3—C19	1.467 (4)	C16—C17	1.423 (4)
N4—C21	1.451 (3)	C17—C18	1.370 (4)
C1—C6	1.377 (4)	C17—H17	0.9300
C1—C2	1.378 (5)	C18—C19	1.392 (4)
C1—H1	0.9300	C18—H18	0.9300
C2—C3	1.347 (6)	C19—C20	1.361 (4)
C2—H2A	0.9300	C20—C21	1.401 (4)
C3—C4	1.359 (6)	C20—H20	0.9300
C3—H3	0.9300	O7—C22	1.193 (4)
C4—C5	1.417 (6)	N5—C22	1.345 (5)
C4—H4	0.9300	N5—C24	1.414 (5)
C5—C6	1.374 (4)	N5—C23	1.449 (5)
C5—H5	0.9300	C22—H22	0.9300
C6—C7	1.502 (4)	C23—H23A	0.9600
C7—H7A	0.9700	C23—H23B	0.9600
C7—H7B	0.9700	C23—H23C	0.9600
C8—C9	1.401 (4)	C24—H24A	0.9600
C8—C13	1.406 (4)	C24—H24B	0.9600
C9—C10	1.379 (4)	C24—H24C	0.9600
C8—O1—C7	117.2 (2)	C13—C12—H12	119.8
C9—O2—C14	119.1 (3)	C12—C13—C8	118.3 (3)
C15—N1—N2	115.9 (2)	C12—C13—C15	122.4 (3)
C16—N2—N1	118.7 (2)	C8—C13—C15	119.2 (2)
C16—N2—H2	120.7	O2—C14—H14A	109.5
N1—N2—H2	120.7	O2—C14—H14B	109.5
O3—N3—O4	123.3 (3)	H14A—C14—H14B	109.5
O3—N3—C19	117.3 (3)	O2—C14—H14C	109.5
O4—N3—C19	119.4 (3)	H14A—C14—H14C	109.5
O5—N4—O6	121.9 (3)	H14B—C14—H14C	109.5
O5—N4—C21	119.2 (3)	N1—C15—C13	120.2 (3)
O6—N4—C21	118.8 (3)	N1—C15—H15	119.9
C6—C1—C2	121.3 (4)	C13—C15—H15	119.9
C6—C1—H1	119.4	N2—C16—C21	123.8 (2)
C2—C1—H1	119.4	N2—C16—C17	119.7 (2)
C3—C2—C1	118.8 (4)	C21—C16—C17	116.5 (2)
C3—C2—H2A	120.6	C18—C17—C16	121.5 (3)
C1—C2—H2A	120.6	C18—C17—H17	119.2
C2—C3—C4	122.5 (5)	C16—C17—H17	119.2
C2—C3—H3	118.8	C17—C18—C19	119.8 (3)
C4—C3—H3	118.8	C17—C18—H18	120.1
C3—C4—C5	118.8 (4)	C19—C18—H18	120.1
C3—C4—H4	120.6	C20—C19—C18	121.3 (3)
C5—C4—H4	120.6	C20—C19—N3	118.7 (3)
C6—C5—C4	119.2 (4)	C18—C19—N3	119.9 (3)
C6—C5—H5	120.4	C19—C20—C21	119.6 (3)
C4—C5—H5	120.4	C19—C20—H20	120.2
C5—C6—C1	119.4 (3)	C21—C20—H20	120.2
C5—C6—C7	120.9 (3)	C20—C21—C16	121.1 (3)
C1—C6—C7	119.7 (3)	C20—C21—N4	116.2 (3)
O1—C7—C6	108.5 (2)	C16—C21—N4	122.7 (2)
O1—C7—H7A	110.0	C22—N5—C24	121.1 (4)
C6—C7—H7A	110.0	C22—N5—C23	121.3 (4)
O1—C7—H7B	110.0	C24—N5—C23	117.6 (4)
C6—C7—H7B	110.0	O7—C22—N5	127.3 (4)
H7A—C7—H7B	108.4	O7—C22—H22	116.3
O1—C8—C9	120.7 (3)	N5—C22—H22	116.3
O1—C8—C13	118.6 (2)	N5—C23—H23A	109.5
C9—C8—C13	120.4 (3)	N5—C23—H23B	109.5
O2—C9—C10	125.9 (3)	H23A—C23—H23B	109.5
O2—C9—C8	113.8 (3)	N5—C23—H23C	109.5
C10—C9—C8	120.3 (3)	H23A—C23—H23C	109.5
C9—C10—C11	119.5 (3)	H23B—C23—H23C	109.5
C9—C10—H10	120.3	N5—C24—H24A	109.5
C11—C10—H10	120.3	N5—C24—H24B	109.5
C12—C11—C10	121.1 (3)	H24A—C24—H24B	109.5
C12—C11—H11	119.5	N5—C24—H24C	109.5
C10—C11—H11	119.5	H24A—C24—H24C	109.5
C11—C12—C13	120.4 (3)	H24B—C24—H24C	109.5
C11—C12—H12	119.8
C15—N1—N2—C16	−179.1 (2)	C9—C8—C13—C15	−179.2 (2)
C6—C1—C2—C3	0.4 (7)	N2—N1—C15—C13	179.2 (2)
C1—C2—C3—C4	0.1 (8)	C12—C13—C15—N1	1.4 (4)
C2—C3—C4—C5	0.0 (7)	C8—C13—C15—N1	−179.6 (2)
C3—C4—C5—C6	−0.6 (6)	N1—N2—C16—C21	173.2 (2)
C4—C5—C6—C1	1.1 (5)	N1—N2—C16—C17	−5.4 (3)
C4—C5—C6—C7	−179.6 (3)	N2—C16—C17—C18	−179.8 (2)
C2—C1—C6—C5	−1.0 (5)	C21—C16—C17—C18	1.6 (4)
C2—C1—C6—C7	179.7 (3)	C16—C17—C18—C19	0.1 (4)
C8—O1—C7—C6	145.3 (2)	C17—C18—C19—C20	−1.3 (4)
C5—C6—C7—O1	−125.6 (3)	C17—C18—C19—N3	−180.0 (3)
C1—C6—C7—O1	53.7 (4)	O3—N3—C19—C20	−171.9 (3)
C7—O1—C8—C9	−68.5 (3)	O4—N3—C19—C20	7.3 (4)
C7—O1—C8—C13	117.5 (3)	O3—N3—C19—C18	6.8 (4)
C14—O2—C9—C10	−6.5 (4)	O4—N3—C19—C18	−174.0 (3)
C14—O2—C9—C8	175.4 (3)	C18—C19—C20—C21	0.7 (4)
O1—C8—C9—O2	4.4 (4)	N3—C19—C20—C21	179.3 (2)
C13—C8—C9—O2	178.2 (2)	C19—C20—C21—C16	1.2 (4)
O1—C8—C9—C10	−173.8 (3)	C19—C20—C21—N4	−177.2 (2)
C13—C8—C9—C10	0.0 (4)	N2—C16—C21—C20	179.2 (2)
O2—C9—C10—C11	−177.7 (3)	C17—C16—C21—C20	−2.2 (4)
C8—C9—C10—C11	0.3 (4)	N2—C16—C21—N4	−2.6 (4)
C9—C10—C11—C12	−0.3 (5)	C17—C16—C21—N4	176.0 (2)
C10—C11—C12—C13	0.1 (4)	O5—N4—C21—C20	6.3 (4)
C11—C12—C13—C8	0.1 (4)	O6—N4—C21—C20	−175.4 (2)
C11—C12—C13—C15	179.1 (2)	O5—N4—C21—C16	−172.0 (3)
O1—C8—C13—C12	173.8 (2)	O6—N4—C21—C16	6.3 (4)
C9—C8—C13—C12	−0.2 (4)	C24—N5—C22—O7	−1.9 (6)
O1—C8—C13—C15	−5.2 (4)	C23—N5—C22—O7	175.6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O6	0.86	2.05	2.653 (3)	126
C15—H15···O7	0.93	2.58	3.369 (4)	143