5-Bromo­salicylaldehyde benzoyl­hydrazone

The title compound, C₁₄H₁₁BrN₂O₂, was synthesized by the reaction of 5-bromo­salicylaldehyde with benzoyl­hydrazine. Inter­molecular N—H...O hydrogen bonds link the mol­ecules into chains running along the a axis. The crystal packing is further stabilized by van der Waals forces.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.031
• wR factor = 0.067
• Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.96
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT432_ALERT_2_C Short Inter X...Y Contact  O1     ..  C1      ..       2.99 Ang.

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           25.01
           From the CIF: _reflns_number_total               2191
           Count of symmetry unique reflns         1208
           Completeness (_total/calc)            181.37%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       983
           Fraction of Friedel pairs measured     0.814
           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
   1 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
   3 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, 1998); 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.

5-bromosalicylaldehyde benzoylhydrazone

Crystal data

C14H11BrN2O2	Dx = 1.618 Mg m^−3
Mr = 319.16	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 2210 reflections
a = 9.534 (3) Å	θ = 2.5–23.8°
b = 9.970 (2) Å	µ = 3.14 mm^−1
c = 13.783 (3) Å	T = 298 K
V = 1310.2 (6) Å^3	Block, colourless
Z = 4	0.42 × 0.20 × 0.15 mm
F(000) = 640

Data collection

Bruker SMART CCD area-detector diffractometer	2191 independent reflections
Radiation source: fine-focus sealed tube	1747 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
φ and ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→11
Tmin = 0.353, Tmax = 0.651	k = −11→11
6496 measured reflections	l = −14→16

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)] = 0.031	H-atom parameters constrained
wR(F^2) = 0.067	w = 1/[σ^2(Fo^2) + (0.028P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
2191 reflections	Δρmax = 0.32 e Å^−3
172 parameters	Δρmin = −0.68 e Å^−3
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.003 (12)

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 > 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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.23149 (4)	0.53528 (4)	0.74755 (6)	0.06001 (15)
N1	0.4993 (3)	0.6907 (3)	0.3355 (2)	0.0380 (7)
N2	0.4589 (2)	0.7205 (2)	0.2432 (3)	0.0377 (6)
H2	0.3797	0.6931	0.2210	0.045*
O1	0.6912 (3)	0.6729 (3)	0.4679 (2)	0.0566 (7)
H1	0.6626	0.6746	0.4118	0.085*
O2	0.6599 (3)	0.8345 (3)	0.21775 (17)	0.0530 (8)
C1	0.4102 (4)	0.6383 (3)	0.3933 (3)	0.0390 (9)
H1A	0.3216	0.6142	0.3712	0.047*
C2	0.4494 (4)	0.6167 (3)	0.4941 (3)	0.0367 (9)
C3	0.5848 (4)	0.6417 (4)	0.5279 (3)	0.0416 (9)
C4	0.6121 (4)	0.6342 (4)	0.6267 (3)	0.0483 (10)
H4	0.7024	0.6509	0.6491	0.058*
C5	0.5083 (4)	0.6025 (4)	0.6920 (3)	0.0466 (9)
H5	0.5272	0.5997	0.7582	0.056*
C6	0.3759 (4)	0.5750 (3)	0.6576 (3)	0.0422 (9)
C7	0.3452 (4)	0.5815 (3)	0.5602 (3)	0.0427 (9)
H7	0.2550	0.5624	0.5385	0.051*
C8	0.5470 (4)	0.7948 (4)	0.1868 (3)	0.0388 (9)
C9	0.4967 (4)	0.8236 (4)	0.0875 (3)	0.0375 (8)
C10	0.4017 (5)	0.7434 (4)	0.0391 (3)	0.0571 (11)
H10	0.3658	0.6672	0.0690	0.069*
C11	0.3604 (5)	0.7765 (5)	−0.0535 (3)	0.0698 (13)
H11	0.2971	0.7220	−0.0865	0.084*
C12	0.4123 (5)	0.8895 (5)	−0.0975 (3)	0.0629 (12)
H12	0.3832	0.9116	−0.1599	0.075*
C13	0.5049 (5)	0.9686 (5)	−0.0511 (3)	0.0588 (11)
H13	0.5390	1.0454	−0.0812	0.071*
C14	0.5490 (4)	0.9360 (4)	0.0408 (3)	0.0506 (11)
H14	0.6147	0.9899	0.0720	0.061*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0681 (3)	0.0725 (3)	0.0394 (2)	−0.0145 (2)	0.0093 (3)	0.0041 (4)
N1	0.0360 (17)	0.0433 (17)	0.035 (2)	0.0044 (14)	0.0000 (15)	−0.0024 (15)
N2	0.0329 (14)	0.0496 (16)	0.0307 (17)	0.0015 (12)	−0.004 (2)	−0.003 (2)
O1	0.0385 (15)	0.088 (2)	0.0438 (18)	−0.0122 (15)	0.0004 (13)	0.0023 (14)
O2	0.0334 (14)	0.0753 (18)	0.050 (2)	−0.0040 (13)	−0.0025 (12)	0.0078 (12)
C1	0.030 (2)	0.047 (2)	0.040 (2)	0.0018 (18)	−0.0010 (17)	−0.0047 (18)
C2	0.038 (2)	0.038 (2)	0.034 (2)	0.0004 (19)	−0.0017 (17)	0.0002 (17)
C3	0.038 (2)	0.044 (2)	0.042 (2)	0.0014 (17)	−0.0025 (18)	−0.0010 (18)
C4	0.045 (2)	0.055 (3)	0.045 (3)	−0.007 (2)	−0.014 (2)	0.0033 (19)
C5	0.060 (3)	0.048 (2)	0.032 (2)	−0.005 (2)	−0.013 (2)	0.0006 (18)
C6	0.051 (2)	0.039 (2)	0.037 (2)	0.0021 (17)	0.0014 (19)	−0.0014 (17)
C7	0.041 (2)	0.046 (2)	0.041 (2)	−0.0052 (18)	−0.0061 (18)	0.0027 (18)
C8	0.034 (2)	0.042 (2)	0.040 (2)	0.0051 (18)	0.0039 (18)	0.0002 (18)
C9	0.034 (2)	0.046 (2)	0.033 (2)	0.0070 (17)	0.0072 (17)	0.0003 (18)
C10	0.072 (3)	0.062 (3)	0.037 (2)	−0.014 (2)	−0.003 (2)	−0.001 (2)
C11	0.085 (4)	0.083 (3)	0.041 (3)	−0.014 (3)	−0.012 (3)	−0.007 (2)
C12	0.075 (3)	0.083 (3)	0.030 (3)	0.014 (3)	0.004 (2)	0.006 (2)
C13	0.056 (3)	0.071 (3)	0.049 (3)	0.008 (3)	0.017 (2)	0.013 (2)
C14	0.048 (3)	0.059 (3)	0.045 (3)	−0.001 (2)	0.008 (2)	0.004 (2)

Geometric parameters (Å, º)

Br1—C6	1.895 (4)	C5—H5	0.9300
N1—C1	1.275 (4)	C6—C7	1.375 (5)
N1—N2	1.362 (5)	C7—H7	0.9300
N2—C8	1.363 (5)	C8—C9	1.479 (5)
N2—H2	0.8600	C9—C10	1.380 (5)
O1—C3	1.345 (4)	C9—C14	1.385 (5)
O1—H1	0.8200	C10—C11	1.376 (6)
O2—C8	1.223 (4)	C10—H10	0.9300
C1—C2	1.456 (5)	C11—C12	1.371 (6)
C1—H1A	0.9300	C11—H11	0.9300
C2—C7	1.392 (5)	C12—C13	1.346 (6)
C2—C3	1.395 (5)	C12—H12	0.9300
C3—C4	1.388 (5)	C13—C14	1.374 (6)
C4—C5	1.374 (5)	C13—H13	0.9300
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.376 (5)
C1—N1—N2	119.0 (3)	C6—C7—H7	120.1
N1—N2—C8	118.5 (3)	C2—C7—H7	120.1
N1—N2—H2	120.8	O2—C8—N2	121.3 (4)
C8—N2—H2	120.8	O2—C8—C9	123.1 (3)
C3—O1—H1	109.5	N2—C8—C9	115.7 (3)
N1—C1—C2	119.1 (3)	C10—C9—C14	118.7 (4)
N1—C1—H1A	120.5	C10—C9—C8	123.2 (4)
C2—C1—H1A	120.5	C14—C9—C8	118.0 (4)
C7—C2—C3	119.2 (3)	C11—C10—C9	119.8 (4)
C7—C2—C1	118.6 (3)	C11—C10—H10	120.1
C3—C2—C1	122.0 (3)	C9—C10—H10	120.1
O1—C3—C4	118.3 (3)	C12—C11—C10	120.2 (4)
O1—C3—C2	122.3 (3)	C12—C11—H11	119.9
C4—C3—C2	119.4 (3)	C10—C11—H11	119.9
C5—C4—C3	121.3 (4)	C13—C12—C11	120.5 (4)
C5—C4—H4	119.3	C13—C12—H12	119.7
C3—C4—H4	119.3	C11—C12—H12	119.7
C4—C5—C6	118.7 (4)	C12—C13—C14	120.0 (4)
C4—C5—H5	120.6	C12—C13—H13	120.0
C6—C5—H5	120.6	C14—C13—H13	120.0
C7—C6—C5	121.5 (4)	C13—C14—C9	120.6 (4)
C7—C6—Br1	119.6 (3)	C13—C14—H14	119.7
C5—C6—Br1	118.8 (3)	C9—C14—H14	119.7
C6—C7—C2	119.9 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.89	2.590 (4)	143
N2—H2···O2^i	0.86	2.11	2.924 (4)	157

Symmetry code: (i) x−1/2, −y+3/2, z.