(E)-N′-(5-Bromo-2-hydroxy­benzyl­idene)furan-2-carbohydrazide monohydrate

Tai, X.-S.; Yin, J.; Hao, M.-Y.; Liang, Z.-P.

doi:10.1107/S1600536807014687

(E)-N′-(5-Bromo-2-hydroxybenzylidene)furan-2-carbohydrazide monohydrate

X.-S. Tai, J. Yin, M.-Y. Hao and Z.-P. Liang

In the title molecule, C₁₂H₉BrN₂O₃·H₂O, the dihedral angle between the benzene and furan rings is 10.0 (2)°. In the crystal structure, (E)-N′-(5-bromo-2-hydroxybenzylidene)furan-2-carbohydrazide molecules and water molecules, are linked by O—H

O and N—H

O hydrogen bonds into a two-dimensional network perpendicular to the c axis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807014687/lh2320sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807014687/lh2320Isup2.hkl Contains datablock I

CCDC reference: 647261

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.005 Å
R factor = 0.029
wR factor = 0.069
Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O3     -   C9      ..       5.72 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C10    -   C11     ..       5.34 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C9

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           25.02
           From the CIF: _reflns_number_total               2238
           Count of symmetry unique reflns         1343
           Completeness (_total/calc)            166.64%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       895
           Fraction of Friedel pairs measured     0.666
           Are heavy atom types Z>Si present        yes

   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
   3 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

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

(E)—N'-(5-bromo-2-hydroxybenzylidene)furan-2-carbohydrazide monohydrate top

Crystal data top

C₁₂H₉BrN₂O₃·H₂O	F(000) = 656
M_r = 327.13	D_x = 1.703 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2741 reflections
a = 4.8880 (8) Å	θ = 2.5–26.0°
b = 12.495 (2) Å	µ = 3.23 mm⁻¹
c = 20.889 (4) Å	T = 294 K
V = 1275.8 (4) Å³	Block, light yellow
Z = 4	0.20 × 0.18 × 0.14 mm

Data collection top

Bruker SMART CCD diffractometer	2238 independent reflections
Radiation source: fine-focus sealed tube	1954 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
φ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −5→5
T_min = 0.541, T_max = 0.634	k = −14→14
6358 measured reflections	l = −12→24

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.029	w = 1/[σ²(F_o²) + (0.0277P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.070	(Δ/σ)_max = 0.001
S = 1.02	Δρ_max = 0.36 e Å⁻³
2238 reflections	Δρ_min = −0.21 e Å⁻³
174 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
15 restraints	Extinction coefficient: 0.0291 (16)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 795 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.007 (11)

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	U_iso*/U_eq
Br1	1.41128 (8)	−0.14792 (3)	0.98063 (2)	0.05003 (17)
O1	0.7552 (6)	0.2278 (2)	0.88643 (12)	0.0511 (7)
H1	0.6507	0.2109	0.8575	0.077*
O2	0.1747 (5)	0.21596 (19)	0.73398 (14)	0.0495 (7)
O3	−0.1923 (6)	0.1312 (2)	0.64777 (14)	0.0615 (8)
N1	0.5121 (6)	0.0871 (2)	0.80357 (13)	0.0334 (7)
N2	0.3298 (5)	0.0499 (2)	0.75851 (14)	0.0337 (7)
H2A	0.3203	−0.0176	0.7507	0.040*
C1	0.8979 (7)	0.1406 (3)	0.90580 (15)	0.0356 (7)
C2	1.0886 (8)	0.1546 (3)	0.95407 (17)	0.0445 (8)
H2	1.1144	0.2224	0.9715	0.053*
C3	1.2397 (7)	0.0705 (3)	0.97663 (18)	0.0404 (8)
H3	1.3663	0.0810	1.0093	0.049*
C4	1.2027 (7)	−0.0304 (3)	0.95040 (18)	0.0367 (8)
C5	1.0162 (7)	−0.0465 (3)	0.90293 (17)	0.0362 (9)
H5	0.9917	−0.1148	0.8862	0.043*
C6	0.8607 (7)	0.0390 (3)	0.87897 (16)	0.0323 (8)
C7	0.6598 (7)	0.0159 (3)	0.82990 (16)	0.0351 (9)
H7	0.6378	−0.0548	0.8170	0.042*
C8	0.1676 (7)	0.1176 (3)	0.72679 (18)	0.0335 (8)
C9	−0.0249 (7)	0.0677 (3)	0.68245 (16)	0.0338 (8)
C10	−0.0712 (9)	−0.0366 (3)	0.6705 (2)	0.0548 (11)
H10	0.0143	−0.0960	0.6883	0.066*
C11	−0.2888 (11)	−0.0333 (5)	0.6227 (3)	0.0758 (16)
H11	−0.3688	−0.0923	0.6030	0.091*
C12	−0.3509 (9)	0.0651 (5)	0.6124 (2)	0.0707 (14)
H12	−0.4867	0.0879	0.5843	0.085*
O4	0.3323 (5)	0.82655 (19)	0.75505 (15)	0.0586 (8)
H4A	0.1861	0.7896	0.7594	0.070*
H4B	0.4797	0.7956	0.7666	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0437 (2)	0.0460 (2)	0.0604 (3)	−0.0003 (2)	−0.0092 (2)	0.01499 (19)
O1	0.0588 (17)	0.0379 (15)	0.0565 (18)	0.0076 (14)	−0.0135 (15)	−0.0044 (13)
O2	0.0410 (16)	0.0263 (13)	0.0812 (19)	0.0029 (11)	−0.0137 (14)	−0.0038 (12)
O3	0.0524 (17)	0.067 (2)	0.0647 (19)	0.0007 (16)	−0.0101 (14)	0.0135 (16)
N1	0.0333 (17)	0.0318 (16)	0.0353 (17)	−0.0022 (13)	−0.0012 (13)	−0.0023 (13)
N2	0.0357 (17)	0.0234 (14)	0.0420 (17)	−0.0038 (13)	−0.0071 (13)	−0.0032 (12)
C1	0.0355 (17)	0.0331 (18)	0.0381 (19)	0.000 (2)	0.0005 (16)	−0.0007 (16)
C2	0.052 (2)	0.0358 (19)	0.0456 (19)	−0.007 (2)	−0.0062 (19)	−0.0080 (17)
C3	0.0359 (18)	0.049 (2)	0.037 (2)	−0.0075 (17)	−0.0073 (19)	0.0026 (18)
C4	0.0298 (17)	0.039 (2)	0.041 (2)	−0.0030 (16)	0.0006 (16)	0.0067 (17)
C5	0.0344 (19)	0.0317 (19)	0.043 (2)	−0.0079 (15)	0.0007 (16)	0.0004 (15)
C6	0.0297 (19)	0.0324 (18)	0.035 (2)	−0.0049 (16)	0.0064 (15)	0.0026 (14)
C7	0.041 (2)	0.0278 (19)	0.036 (2)	−0.0035 (16)	0.0010 (16)	−0.0025 (15)
C8	0.0254 (19)	0.032 (2)	0.043 (2)	0.0011 (14)	0.0029 (15)	0.0016 (15)
C9	0.0295 (18)	0.037 (2)	0.0351 (19)	0.0024 (15)	−0.0004 (15)	0.0028 (15)
C10	0.046 (2)	0.028 (2)	0.091 (3)	−0.0015 (19)	−0.001 (3)	−0.0013 (19)
C11	0.061 (3)	0.085 (4)	0.082 (4)	−0.035 (3)	0.015 (3)	−0.049 (3)
C12	0.050 (3)	0.112 (4)	0.050 (3)	−0.019 (3)	−0.014 (2)	0.001 (3)
O4	0.0442 (17)	0.0287 (15)	0.103 (2)	−0.0017 (12)	−0.0168 (15)	0.0056 (13)

Geometric parameters (Å, º) top

Br1—C4	1.895 (4)	C3—H3	0.9300
O1—C1	1.356 (4)	C4—C5	1.362 (5)
O1—H1	0.8200	C5—C6	1.403 (5)
O2—C8	1.238 (4)	C5—H5	0.9300
O3—C9	1.351 (4)	C6—C7	1.448 (5)
O3—C12	1.352 (5)	C7—H7	0.9300
N1—C7	1.271 (4)	C8—C9	1.460 (5)
N1—N2	1.377 (4)	C9—C10	1.346 (5)
N2—C8	1.336 (4)	C10—C11	1.460 (7)
N2—H2A	0.8600	C10—H10	0.9300
C1—C2	1.384 (5)	C11—C12	1.285 (8)
C1—C6	1.400 (5)	C11—H11	0.9300
C2—C3	1.368 (5)	C12—H12	0.9300
C2—H2	0.9300	O4—H4A	0.8554
C3—C4	1.387 (5)	O4—H4B	0.8526

C1—O1—H1	109.5	C1—C6—C7	123.5 (3)
C9—O3—C12	106.4 (4)	C5—C6—C7	117.9 (3)
C7—N1—N2	115.3 (3)	N1—C7—C6	123.5 (3)
C8—N2—N1	120.6 (3)	N1—C7—H7	118.3
C8—N2—H2A	119.7	C6—C7—H7	118.3
N1—N2—H2A	119.7	O2—C8—N2	123.5 (3)
O1—C1—C2	117.5 (3)	O2—C8—C9	121.3 (3)
O1—C1—C6	122.9 (3)	N2—C8—C9	115.2 (3)
C2—C1—C6	119.6 (3)	C10—C9—O3	111.5 (3)
C3—C2—C1	121.2 (3)	C10—C9—C8	129.8 (3)
C3—C2—H2	119.4	O3—C9—C8	118.7 (3)
C1—C2—H2	119.4	C9—C10—C11	102.9 (4)
C2—C3—C4	119.5 (3)	C9—C10—H10	128.6
C2—C3—H3	120.3	C11—C10—H10	128.6
C4—C3—H3	120.3	C12—C11—C10	108.3 (4)
C5—C4—C3	120.6 (3)	C12—C11—H11	125.9
C5—C4—Br1	119.3 (3)	C10—C11—H11	125.9
C3—C4—Br1	120.2 (3)	C11—C12—O3	111.0 (5)
C4—C5—C6	120.7 (3)	C11—C12—H12	124.5
C4—C5—H5	119.6	O3—C12—H12	124.5
C6—C5—H5	119.6	H4A—O4—H4B	115.6
C1—C6—C5	118.5 (3)

C7—N1—N2—C8	−178.7 (3)	C1—C6—C7—N1	5.0 (5)
O1—C1—C2—C3	179.6 (3)	C5—C6—C7—N1	−178.2 (3)
C6—C1—C2—C3	−0.7 (6)	N1—N2—C8—O2	2.2 (5)
C1—C2—C3—C4	0.4 (6)	N1—N2—C8—C9	−177.3 (3)
C2—C3—C4—C5	−0.5 (6)	C12—O3—C9—C10	−0.1 (4)
C2—C3—C4—Br1	179.7 (3)	C12—O3—C9—C8	−178.6 (3)
C3—C4—C5—C6	0.9 (5)	O2—C8—C9—C10	−176.6 (4)
Br1—C4—C5—C6	−179.3 (2)	N2—C8—C9—C10	2.9 (6)
O1—C1—C6—C5	−179.2 (3)	O2—C8—C9—O3	1.7 (5)
C2—C1—C6—C5	1.1 (5)	N2—C8—C9—O3	−178.8 (3)
O1—C1—C6—C7	−2.5 (5)	O3—C9—C10—C11	0.7 (5)
C2—C1—C6—C7	177.8 (3)	C8—C9—C10—C11	179.1 (4)
C4—C5—C6—C1	−1.2 (5)	C9—C10—C11—C12	−1.2 (5)
C4—C5—C6—C7	−178.1 (3)	C10—C11—C12—O3	1.2 (6)
N2—N1—C7—C6	−179.1 (3)	C9—O3—C12—C11	−0.8 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O4ⁱ	0.86	1.95	2.792 (3)	166
O1—H1···N1	0.82	2.03	2.738 (4)	145
O4—H4A···O2ⁱⁱ	0.86	1.99	2.847 (3)	174
O4—H4B···O2ⁱⁱⁱ	0.85	1.96	2.787 (3)	163
C7—H7···O4ⁱ	0.93	2.47	3.257 (4)	142
C10—H10···O4ⁱ	0.93	2.30	3.152 (5)	152

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

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(E)-N′-(5-Bromo-2-hydroxy­benzyl­idene)furan-2-carbohydrazide monohydrate

Supporting information

Key indicators

checkCIF/PLATON results

(E)-N′-(5-Bromo-2-hydroxybenzylidene)furan-2-carbohydrazide monohydrate