The crystals of the title compound, C
15H
15N
3O
4, were obtained from a condensation reaction of 2,4-dimethoxybenzaldehyde and 4-nitrophenylhydrazine. The molecule displays a nearly planar structure. The overlapped arrangement of nearly parallel benzene rings of neighboring molecules and centroid–centroid distance of 3.5642 (16) Å suggest π–π stacking. Adjacent molecules are linked to each other
via N—H
O hydrogen bonds to form a helical supramolecular structure.
Supporting information
CCDC reference: 255914
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- R factor = 0.041
- wR factor = 0.087
- Data-to-parameter ratio = 8.5
checkCIF/PLATON results
No syntax errors found
Alert level C
STRVA01_ALERT_2_C Chirality of atom sites is inverted?
From the CIF: _refine_ls_abs_structure_Flack 10.000
From the CIF: _refine_ls_abs_structure_Flack_su 10.000
PLAT032_ALERT_4_C Std Uncertainty in Flack Parameter too High .... 10.00
PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... 10.00
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 27.30
From the CIF: _reflns_number_total 1684
Count of symmetry unique reflns 1684
Completeness (_total/calc) 100.00%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and XP (Siemens, 1994); software used to prepare material for publication: WinGX (Farrugia, 1999).
3,4-Dimethoxybenzaldehyde 4-nitrophenylhydrazone
top
Crystal data top
C15H15N3O4 | Dx = 1.364 Mg m−3 |
Mr = 301.30 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P41 | Cell parameters from 11397 reflections |
Hall symbol: P 4w | θ = 3.0–27.0° |
a = 7.7618 (12) Å | µ = 0.10 mm−1 |
c = 24.3500 (17) Å | T = 295 K |
V = 1467.0 (3) Å3 | Prism, yellow |
Z = 4 | 0.40 × 0.24 × 0.20 mm |
F(000) = 632 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 1399 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.035 |
Graphite monochromator | θmax = 27.3°, θmin = 2.6° |
Detector resolution: 10.00 pixels mm-1 | h = −10→10 |
ω scans | k = −10→9 |
13519 measured reflections | l = −31→29 |
1684 independent reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.087 | w = 1/[σ2(Fo2) + (0.0368P)2 + 0.1321P] where P = (Fo2 + 2Fc2)/3 |
S = 1.13 | (Δ/σ)max < 0.001 |
1684 reflections | Δρmax = 0.11 e Å−3 |
199 parameters | Δρmin = −0.13 e Å−3 |
1 restraint | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 10 (10) |
Special details top
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 >
σ(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 (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 1.1219 (4) | 1.3403 (3) | 0.49443 (12) | 0.0994 (8) | |
O2 | 1.0046 (4) | 1.2624 (3) | 0.57067 (11) | 0.1010 (9) | |
O3 | 0.4702 (3) | 0.1171 (2) | 0.59674 (7) | 0.0636 (5) | |
O4 | 0.3739 (3) | −0.1545 (2) | 0.54727 (8) | 0.0617 (5) | |
N1 | 1.0434 (4) | 1.2361 (4) | 0.52231 (12) | 0.0720 (7) | |
N2 | 0.8234 (3) | 0.6292 (3) | 0.42289 (9) | 0.0566 (6) | |
H2A | 0.8437 | 0.6148 | 0.3885 | 0.068* | |
N3 | 0.7335 (3) | 0.5088 (3) | 0.45134 (8) | 0.0521 (5) | |
C1 | 0.9926 (3) | 1.0748 (4) | 0.49763 (11) | 0.0541 (7) | |
C2 | 0.9004 (3) | 0.9568 (4) | 0.52814 (11) | 0.0575 (7) | |
H2 | 0.8753 | 0.9795 | 0.5648 | 0.069* | |
C3 | 0.8461 (3) | 0.8065 (4) | 0.50455 (10) | 0.0534 (6) | |
H3 | 0.7856 | 0.7263 | 0.5254 | 0.064* | |
C4 | 0.8812 (3) | 0.7726 (3) | 0.44891 (10) | 0.0490 (6) | |
C5 | 0.9784 (3) | 0.8928 (3) | 0.41938 (11) | 0.0548 (6) | |
H5 | 1.0063 | 0.8704 | 0.3829 | 0.066* | |
C6 | 1.0329 (4) | 1.0421 (4) | 0.44305 (12) | 0.0565 (7) | |
H6 | 1.0965 | 1.1215 | 0.4229 | 0.068* | |
C7 | 0.6882 (3) | 0.3720 (4) | 0.42631 (10) | 0.0527 (6) | |
H7 | 0.7141 | 0.3584 | 0.3893 | 0.063* | |
C8 | 0.5960 (3) | 0.2367 (3) | 0.45544 (10) | 0.0476 (6) | |
C9 | 0.5706 (3) | 0.2494 (3) | 0.51243 (10) | 0.0460 (6) | |
H9 | 0.6058 | 0.3482 | 0.5309 | 0.055* | |
C10 | 0.4948 (3) | 0.1185 (3) | 0.54094 (9) | 0.0457 (6) | |
C11 | 0.4413 (3) | −0.0304 (3) | 0.51354 (10) | 0.0473 (6) | |
C12 | 0.4615 (3) | −0.0433 (3) | 0.45761 (10) | 0.0529 (6) | |
H12 | 0.4230 | −0.1408 | 0.4391 | 0.063* | |
C13 | 0.5398 (3) | 0.0898 (4) | 0.42889 (10) | 0.0538 (6) | |
H13 | 0.5546 | 0.0800 | 0.3911 | 0.065* | |
C14 | 0.5109 (5) | 0.2697 (4) | 0.62573 (12) | 0.0842 (11) | |
H14A | 0.4882 | 0.2531 | 0.6641 | 0.126* | |
H14B | 0.4416 | 0.3628 | 0.6121 | 0.126* | |
H14C | 0.6305 | 0.2966 | 0.6206 | 0.126* | |
C15 | 0.3152 (4) | −0.3117 (4) | 0.52277 (13) | 0.0680 (8) | |
H15A | 0.2710 | −0.3866 | 0.5508 | 0.102* | |
H15B | 0.4095 | −0.3670 | 0.5044 | 0.102* | |
H15C | 0.2258 | −0.2867 | 0.4967 | 0.102* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.112 (2) | 0.0787 (16) | 0.107 (2) | −0.0272 (15) | 0.0052 (16) | −0.0065 (15) |
O2 | 0.152 (3) | 0.0870 (17) | 0.0639 (14) | −0.0032 (16) | −0.0100 (16) | −0.0169 (13) |
O3 | 0.0926 (14) | 0.0572 (11) | 0.0410 (9) | −0.0150 (10) | 0.0099 (10) | −0.0025 (8) |
O4 | 0.0760 (13) | 0.0531 (10) | 0.0560 (10) | −0.0142 (9) | −0.0003 (10) | 0.0003 (9) |
N1 | 0.0725 (17) | 0.0696 (16) | 0.0739 (18) | 0.0063 (14) | −0.0149 (14) | −0.0059 (15) |
N2 | 0.0656 (14) | 0.0632 (14) | 0.0410 (11) | −0.0077 (11) | 0.0148 (10) | 0.0034 (11) |
N3 | 0.0489 (12) | 0.0633 (14) | 0.0441 (11) | 0.0003 (11) | 0.0058 (9) | 0.0067 (11) |
C1 | 0.0470 (14) | 0.0605 (16) | 0.0548 (17) | 0.0071 (12) | −0.0085 (12) | −0.0013 (13) |
C2 | 0.0515 (15) | 0.0792 (19) | 0.0419 (13) | 0.0079 (14) | −0.0023 (12) | −0.0010 (13) |
C3 | 0.0487 (14) | 0.0697 (17) | 0.0418 (13) | −0.0009 (13) | 0.0039 (11) | 0.0075 (13) |
C4 | 0.0414 (13) | 0.0583 (15) | 0.0472 (14) | 0.0061 (11) | 0.0030 (11) | 0.0043 (12) |
C5 | 0.0541 (15) | 0.0638 (17) | 0.0465 (14) | 0.0039 (13) | 0.0117 (12) | 0.0055 (13) |
C6 | 0.0515 (15) | 0.0596 (17) | 0.0584 (15) | 0.0014 (12) | 0.0053 (13) | 0.0099 (13) |
C7 | 0.0533 (15) | 0.0662 (17) | 0.0384 (12) | 0.0026 (13) | 0.0039 (11) | 0.0036 (12) |
C8 | 0.0433 (13) | 0.0566 (15) | 0.0427 (12) | 0.0070 (11) | −0.0027 (11) | 0.0029 (11) |
C9 | 0.0480 (13) | 0.0464 (13) | 0.0434 (12) | 0.0018 (11) | −0.0005 (11) | −0.0021 (11) |
C10 | 0.0483 (14) | 0.0503 (14) | 0.0383 (12) | 0.0057 (11) | 0.0009 (11) | −0.0007 (11) |
C11 | 0.0420 (12) | 0.0502 (14) | 0.0498 (13) | 0.0012 (11) | −0.0021 (11) | 0.0034 (11) |
C12 | 0.0524 (15) | 0.0565 (16) | 0.0497 (15) | −0.0032 (12) | −0.0079 (12) | −0.0091 (12) |
C13 | 0.0554 (16) | 0.0701 (18) | 0.0359 (12) | 0.0045 (13) | −0.0032 (11) | −0.0049 (12) |
C14 | 0.140 (3) | 0.071 (2) | 0.0418 (15) | −0.019 (2) | 0.0133 (18) | −0.0100 (14) |
C15 | 0.0734 (19) | 0.0533 (16) | 0.077 (2) | −0.0067 (14) | −0.0109 (16) | −0.0008 (15) |
Geometric parameters (Å, º) top
O1—N1 | 1.220 (3) | C5—H5 | 0.9300 |
O2—N1 | 1.232 (4) | C6—H6 | 0.9300 |
O3—C10 | 1.372 (3) | C7—C8 | 1.455 (4) |
O3—C14 | 1.414 (4) | C7—H7 | 0.9300 |
O4—C11 | 1.370 (3) | C8—C13 | 1.382 (4) |
O4—C15 | 1.432 (3) | C8—C9 | 1.405 (4) |
N1—C1 | 1.443 (4) | C9—C10 | 1.364 (4) |
N2—C4 | 1.357 (3) | C9—H9 | 0.9300 |
N2—N3 | 1.357 (3) | C10—C11 | 1.397 (3) |
N2—H2A | 0.8600 | C11—C12 | 1.375 (4) |
N3—C7 | 1.274 (3) | C12—C13 | 1.388 (4) |
C1—C2 | 1.379 (4) | C12—H12 | 0.9300 |
C1—C6 | 1.389 (4) | C13—H13 | 0.9300 |
C2—C3 | 1.367 (4) | C14—H14A | 0.9600 |
C2—H2 | 0.9300 | C14—H14B | 0.9600 |
C3—C4 | 1.407 (4) | C14—H14C | 0.9600 |
C3—H3 | 0.9300 | C15—H15A | 0.9600 |
C4—C5 | 1.399 (4) | C15—H15B | 0.9600 |
C5—C6 | 1.362 (4) | C15—H15C | 0.9600 |
| | | |
C10—O3—C14 | 117.2 (2) | C13—C8—C9 | 118.4 (2) |
C11—O4—C15 | 118.1 (2) | C13—C8—C7 | 121.5 (2) |
O1—N1—O2 | 122.9 (3) | C9—C8—C7 | 120.0 (2) |
O1—N1—C1 | 118.7 (3) | C10—C9—C8 | 120.7 (2) |
O2—N1—C1 | 118.4 (3) | C10—C9—H9 | 119.6 |
C4—N2—N3 | 119.8 (2) | C8—C9—H9 | 119.6 |
C4—N2—H2A | 120.1 | C9—C10—O3 | 124.7 (2) |
N3—N2—H2A | 120.1 | C9—C10—C11 | 120.1 (2) |
C7—N3—N2 | 118.2 (2) | O3—C10—C11 | 115.1 (2) |
C2—C1—C6 | 120.7 (3) | O4—C11—C12 | 125.9 (2) |
C2—C1—N1 | 119.5 (3) | O4—C11—C10 | 114.1 (2) |
C6—C1—N1 | 119.7 (3) | C12—C11—C10 | 120.0 (2) |
C3—C2—C1 | 120.0 (3) | C11—C12—C13 | 119.7 (2) |
C3—C2—H2 | 120.0 | C11—C12—H12 | 120.2 |
C1—C2—H2 | 120.0 | C13—C12—H12 | 120.2 |
C2—C3—C4 | 120.3 (2) | C8—C13—C12 | 121.1 (2) |
C2—C3—H3 | 119.8 | C8—C13—H13 | 119.4 |
C4—C3—H3 | 119.8 | C12—C13—H13 | 119.4 |
N2—C4—C5 | 119.0 (2) | O3—C14—H14A | 109.5 |
N2—C4—C3 | 122.6 (2) | O3—C14—H14B | 109.5 |
C5—C4—C3 | 118.3 (2) | H14A—C14—H14B | 109.5 |
C6—C5—C4 | 121.2 (3) | O3—C14—H14C | 109.5 |
C6—C5—H5 | 119.4 | H14A—C14—H14C | 109.5 |
C4—C5—H5 | 119.4 | H14B—C14—H14C | 109.5 |
C5—C6—C1 | 119.4 (3) | O4—C15—H15A | 109.5 |
C5—C6—H6 | 120.3 | O4—C15—H15B | 109.5 |
C1—C6—H6 | 120.3 | H15A—C15—H15B | 109.5 |
N3—C7—C8 | 120.3 (2) | O4—C15—H15C | 109.5 |
N3—C7—H7 | 119.9 | H15A—C15—H15C | 109.5 |
C8—C7—H7 | 119.9 | H15B—C15—H15C | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O3i | 0.86 | 2.44 | 3.038 (3) | 127 |
N2—H2A···O4i | 0.86 | 2.22 | 3.063 (3) | 166 |
Symmetry code: (i) y+1, −x+1, z−1/4. |