Literature DB >> 22065140

N'-(3,5-Dibromo-2-hy-droxy-benzyl-idene)-4-nitro-benzohydrazide methanol monosolvate.

Abstract

The title compound, C(14)H(9)Br(2)N(3)O(4)·CH(4)O, was obtained as the product of the reaction of 3,5-dibromo-salicyl-aldehyde with 4-nitro-benzohydrazide in methanol. The benzohydrazide mol-ecule is nearly planar, with a maximum deviation of 0.126 (2) Å. The mean planes of the two benzene rings make a dihedral angle of 9.3 (3)°. Intra-molecular O-H⋯N and O-H⋯Br inter-actions are observed in the benzohydrazide mol-ecule. In the crystal, pairs of adjacent benzohydrazide mol-ecules are linked by two methanol mol-ecules through inter-molecular O-H⋯O and N-H⋯O hydrogen bonds, forming a dimer.

Entities: Chemical Disease Species

Year: 2011 PMID： 22065140 PMCID： PMC3200651 DOI： 10.1107/S1600536811031187

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For the biological activity of benzohydrazide compounds, see: El-Sayed et al. (2011 ▶); Horiuchi et al. (2009 ▶). For coordination compounds involving benzohydrazides, see: El-Dissouky et al. (2010 ▶); Zhang et al. (2010 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For related structures, see: Suleiman Gwaram et al. (2010 ▶); Dai & Mao (2010 ▶); Ban (2010 ▶).

Experimental

Crystal data

C14H9Br2N3O4·CH4O M = 475.10 Monoclinic, a = 7.576 (2) Å b = 13.602 (2) Å c = 17.230 (3) Å β = 106.816 (3)° V = 1699.6 (6) Å3 Z = 4 Mo Kα radiation μ = 4.80 mm−1 T = 298 K 0.30 × 0.27 × 0.27 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.327, T max = 0.357 10168 measured reflections 3685 independent reflections 2011 reflections with I > 2σ(I) R int = 0.075

Refinement

R[F 2 > 2σ(F 2)] = 0.049 wR(F 2) = 0.103 S = 1.00 3685 reflections 227 parameters H-atom parameters constrained Δρmax = 0.53 e Å−3 Δρmin = −0.52 e Å−3 Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811031187/qm2019sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031187/qm2019Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811031187/qm2019Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₄H₉Br₂N₃O₄·CH₄O	F(000) = 936
M_r = 475.10	D_x = 1.857 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.576 (2) Å	Cell parameters from 1293 reflections
b = 13.602 (2) Å	θ = 2.5–24.5°
c = 17.230 (3) Å	µ = 4.80 mm⁻¹
β = 106.816 (3)°	T = 298 K
V = 1699.6 (6) Å³	Block, yellow
Z = 4	0.30 × 0.27 × 0.27 mm

Bruker SMART 1K CCD area-detector diffractometer	3685 independent reflections
Radiation source: fine-focus sealed tube	2011 reflections with I > 2σ(I)
graphite	R_int = 0.075
ω scans	θ_max = 27.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→9
T_min = 0.327, T_max = 0.357	k = −15→17
10168 measured reflections	l = −22→13

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.P)²] where P = (F_o² + 2F_c²)/3
3685 reflections	(Δ/σ)_max = 0.001
227 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.52 e Å⁻³

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.

	x	y	z	U_iso*/U_eq
Br1	0.83099 (8)	1.22176 (4)	0.84550 (4)	0.0533 (2)
Br2	0.79926 (8)	0.82702 (4)	0.94026 (3)	0.0492 (2)
O1	0.5709 (5)	1.1483 (2)	0.6907 (2)	0.0470 (10)
H1	0.5200	1.1265	0.6454	0.056*
O2	0.2149 (5)	1.1321 (3)	0.4660 (2)	0.0584 (11)
O3	−0.3295 (6)	0.8090 (4)	0.1561 (3)	0.0822 (16)
O4	−0.3194 (7)	0.9500 (4)	0.1026 (3)	0.0953 (17)
N1	0.3873 (5)	1.0128 (3)	0.5892 (2)	0.0384 (11)
N2	0.2818 (5)	0.9780 (3)	0.5145 (2)	0.0404 (11)
H2	0.3046	0.9146	0.5048	0.048*
N3	−0.2750 (6)	0.8932 (5)	0.1592 (3)	0.0576 (15)
C1	0.5601 (6)	0.9761 (3)	0.7247 (3)	0.0320 (12)
C2	0.6184 (6)	1.0736 (4)	0.7435 (3)	0.0321 (12)
C3	0.7351 (6)	1.0935 (4)	0.8209 (3)	0.0355 (13)
C4	0.7889 (6)	1.0222 (4)	0.8791 (3)	0.0383 (13)
H4	0.8662	1.0374	0.9303	0.046*
C5	0.7259 (6)	0.9266 (4)	0.8603 (3)	0.0355 (12)
C6	0.6146 (6)	0.9041 (3)	0.7845 (3)	0.0347 (12)
H6	0.5747	0.8397	0.7727	0.042*
C7	0.4506 (7)	0.9483 (4)	0.6443 (3)	0.0388 (13)
H7	0.4256	0.8821	0.6323	0.047*
C8	0.1984 (7)	1.0439 (4)	0.4568 (3)	0.0365 (13)
C9	0.0789 (6)	0.9994 (4)	0.3795 (3)	0.0326 (12)
C10	0.0309 (7)	1.0598 (4)	0.3111 (3)	0.0397 (13)
H10	0.0768	1.1235	0.3141	0.048*
C11	−0.0849 (7)	1.0247 (4)	0.2391 (3)	0.0429 (14)
H11	−0.1175	1.0645	0.1932	0.052*
C12	−0.1505 (7)	0.9317 (4)	0.2361 (3)	0.0417 (14)
C13	−0.1068 (7)	0.8708 (4)	0.3030 (3)	0.0498 (15)
H13	−0.1535	0.8072	0.2993	0.060*
C14	0.0068 (7)	0.9054 (4)	0.3751 (3)	0.0419 (14)
H14	0.0352	0.8656	0.4209	0.050*
O5	0.4000 (5)	0.7107 (3)	0.9877 (2)	0.0612 (11)
H5	0.5128	0.7097	0.9988	0.073*
C15	0.3336 (8)	0.8036 (4)	0.9540 (4)	0.0627 (18)
H15A	0.3740	0.8154	0.9069	0.094*
H15B	0.3807	0.8542	0.9934	0.094*
H15C	0.2013	0.8039	0.9389	0.094*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0592 (4)	0.0348 (4)	0.0627 (4)	−0.0076 (3)	0.0125 (3)	−0.0113 (3)
Br2	0.0522 (4)	0.0489 (4)	0.0435 (4)	0.0081 (3)	0.0087 (3)	0.0129 (3)
O1	0.064 (2)	0.031 (2)	0.038 (2)	0.0028 (18)	0.0037 (19)	0.0001 (17)
O2	0.086 (3)	0.027 (2)	0.050 (3)	0.004 (2)	−0.001 (2)	−0.0070 (19)
O3	0.072 (3)	0.088 (4)	0.073 (3)	−0.020 (3)	0.000 (3)	−0.039 (3)
O4	0.111 (4)	0.104 (4)	0.042 (3)	0.017 (3)	−0.023 (3)	−0.004 (3)
N1	0.035 (2)	0.043 (3)	0.034 (3)	0.001 (2)	0.006 (2)	−0.008 (2)
N2	0.051 (3)	0.033 (3)	0.033 (3)	0.004 (2)	0.006 (2)	−0.007 (2)
N3	0.042 (3)	0.086 (5)	0.037 (3)	0.010 (3)	−0.001 (3)	−0.022 (3)
C1	0.032 (3)	0.028 (3)	0.034 (3)	−0.001 (2)	0.007 (2)	−0.001 (2)
C2	0.032 (3)	0.034 (3)	0.029 (3)	0.008 (2)	0.008 (2)	0.005 (2)
C3	0.033 (3)	0.032 (3)	0.042 (3)	−0.002 (2)	0.013 (3)	−0.007 (2)
C4	0.032 (3)	0.044 (4)	0.032 (3)	0.003 (2)	−0.001 (2)	−0.010 (3)
C5	0.035 (3)	0.033 (3)	0.037 (3)	0.003 (2)	0.008 (3)	0.005 (2)
C6	0.040 (3)	0.026 (3)	0.037 (3)	−0.001 (2)	0.011 (3)	−0.002 (2)
C7	0.045 (3)	0.035 (3)	0.035 (3)	−0.001 (3)	0.010 (3)	−0.005 (3)
C8	0.036 (3)	0.039 (4)	0.034 (3)	0.002 (3)	0.009 (3)	−0.003 (3)
C9	0.035 (3)	0.029 (3)	0.035 (3)	0.007 (2)	0.013 (3)	0.000 (2)
C10	0.044 (3)	0.035 (3)	0.039 (3)	0.008 (3)	0.010 (3)	−0.002 (3)
C11	0.045 (3)	0.053 (4)	0.031 (3)	0.015 (3)	0.011 (3)	0.009 (3)
C12	0.029 (3)	0.057 (4)	0.037 (3)	0.000 (3)	0.006 (3)	−0.012 (3)
C13	0.058 (4)	0.043 (4)	0.043 (4)	−0.006 (3)	0.006 (3)	−0.004 (3)
C14	0.045 (3)	0.037 (3)	0.038 (3)	−0.004 (3)	0.004 (3)	0.003 (3)
O5	0.050 (2)	0.056 (3)	0.070 (3)	−0.007 (2)	0.004 (2)	0.014 (2)
C15	0.058 (4)	0.048 (4)	0.079 (5)	0.002 (3)	0.015 (4)	0.007 (3)

Br1—C3	1.890 (5)	C5—C6	1.368 (6)
Br2—C5	1.898 (5)	C6—H6	0.9300
O1—C2	1.341 (5)	C7—H7	0.9300
O1—H1	0.8200	C8—C9	1.505 (6)
O2—C8	1.212 (5)	C9—C14	1.383 (6)
O3—N3	1.214 (6)	C9—C10	1.396 (6)
O4—N3	1.213 (6)	C10—C11	1.381 (7)
N1—C7	1.280 (6)	C10—H10	0.9300
N1—N2	1.389 (5)	C11—C12	1.355 (7)
N2—C8	1.352 (6)	C11—H11	0.9300
N2—H2	0.9035	C12—C13	1.379 (7)
N3—C12	1.483 (6)	C13—C14	1.374 (7)
C1—C6	1.395 (6)	C13—H13	0.9300
C1—C2	1.406 (6)	C14—H14	0.9300
C1—C7	1.444 (6)	O5—C15	1.420 (6)
C2—C3	1.398 (6)	O5—H5	0.8200
C3—C4	1.369 (6)	C15—H15A	0.9600
C4—C5	1.390 (6)	C15—H15B	0.9600
C4—H4	0.9300	C15—H15C	0.9600

C2—O1—H1	109.4	O2—C8—N2	123.5 (5)
C7—N1—N2	116.4 (4)	O2—C8—C9	121.8 (5)
C8—N2—N1	118.5 (4)	N2—C8—C9	114.7 (5)
C8—N2—H2	124.8	C14—C9—C10	119.7 (5)
N1—N2—H2	114.0	C14—C9—C8	123.2 (5)
O4—N3—O3	123.7 (5)	C10—C9—C8	117.0 (5)
O4—N3—C12	116.8 (6)	C11—C10—C9	119.8 (5)
O3—N3—C12	119.5 (6)	C11—C10—H10	120.1
C6—C1—C2	119.1 (4)	C9—C10—H10	120.1
C6—C1—C7	119.3 (5)	C12—C11—C10	119.2 (5)
C2—C1—C7	121.5 (4)	C12—C11—H11	120.4
O1—C2—C3	118.2 (4)	C10—C11—H11	120.4
O1—C2—C1	123.6 (4)	C11—C12—C13	122.2 (5)
C3—C2—C1	118.2 (4)	C11—C12—N3	119.6 (5)
C4—C3—C2	122.2 (5)	C13—C12—N3	118.2 (5)
C4—C3—Br1	118.4 (4)	C14—C13—C12	119.1 (5)
C2—C3—Br1	119.3 (4)	C14—C13—H13	120.5
C3—C4—C5	118.9 (4)	C12—C13—H13	120.5
C3—C4—H4	120.6	C13—C14—C9	120.0 (5)
C5—C4—H4	120.6	C13—C14—H14	120.0
C6—C5—C4	120.5 (4)	C9—C14—H14	120.0
C6—C5—Br2	120.2 (4)	C15—O5—H5	109.4
C4—C5—Br2	119.3 (4)	O5—C15—H15A	109.5
C5—C6—C1	121.1 (5)	O5—C15—H15B	109.5
C5—C6—H6	119.4	H15A—C15—H15B	109.5
C1—C6—H6	119.4	O5—C15—H15C	109.5
N1—C7—C1	121.3 (5)	H15A—C15—H15C	109.5
N1—C7—H7	119.4	H15B—C15—H15C	109.5
C1—C7—H7	119.4

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.94	2.642 (5)	143.
N2—H2···O5ⁱ	0.90	1.91	2.800 (5)	169.
O5—H5···O2ⁱⁱ	0.82	2.24	2.991 (6)	153.
O5—H5···Br2	0.82	3.09	3.708 (4)	134.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.94	2.642 (5)	143
N2—H2⋯O5ⁱ	0.90	1.91	2.800 (5)	169
O5—H5⋯O2ⁱⁱ	0.82	2.24	2.991 (6)	153
O5—H5⋯Br2	0.82	3.09	3.708 (4)	134

Symmetry codes: (i) ; (ii) .

6 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. N'-[1-(5-Bromo-2-hydroxy-phen-yl)ethyl-idene]-3,4,5-trihydroxy-benzohydrazide dimethyl sulfoxide solvate trihydrate.

Authors: Nura Suleiman Gwaram; Hamid Khaledi; Hapipah Mohd Ali; Ward T Robinson; Mahmood A Abdulla
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-02-27

3. Discovery of novel thieno[2,3-d]pyrimidin-4-yl hydrazone-based inhibitors of cyclin D1-CDK4: synthesis, biological evaluation and structure-activity relationships. Part 2.

Authors: Takao Horiuchi; Motoko Nagata; Mayumi Kitagawa; Kouichi Akahane; Kouichi Uoto
Journal: Bioorg Med Chem Date: 2009-10-24 Impact factor: 3.641

4. (E)-4-Meth-oxy-N'-(4-nitro-benzyl-idene)benzohydrazide methanol monosolvate.

Authors: Hong-Yan Ban
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-11-20

5. N'-(4-Hy-droxy-benzyl-idene)-4-nitro-benzohydrazide.

Authors: Chun-Hua Dai; Fu-Lin Mao
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-10-23

6. [2-Hydroxy-N'-(4-oxo-4-phenyl-butan-2-yl-idene)benzohydrazidato(2-)]pyridine-copper(II).

Authors: Shu-Ping Zhang; Ying Wei; Si-Chang Shao
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-11-24