Redetermination of 3-hydroxy­benzamide

The crystal structure of the title compound, C₇H₇NO₂, has been redetermined [Katsube, Y. (1966). Bull. Chem. Soc. Jpn, 39, 2576-2588] to higher precision and with the hydrogen-bonding scheme established.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.046
• wR factor = 0.033
• Data-to-parameter ratio = 9.3

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.86

Author Response: Due to not so good quality of the single crystal. For this compound it is very difficult to prepare the single crystals.

Alert level B
REFLT03_ALERT_3_B  Reflection count < 90% complete (theta max?)
           From the CIF: _diffrn_reflns_theta_max           30.67
           From the CIF: _diffrn_reflns_theta_full          30.67
           From the CIF: _reflns_number_total               1707
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         1991
           Completeness (_total/calc)             85.74%
PLAT411_ALERT_2_B Short Inter H...H Contact  H1     ..  H1      ..       2.06 Ang.

Alert level C
REFNR01_ALERT_3_C  Ratio of reflections to parameters is < 10 for a
            centrosymmetric structure
            sine(theta)/lambda                0.7177
            Proportion of unique data used    0.6462
            Ratio reflections to parameters   9.2689
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       9.27
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.07 Ratio

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K

   1 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 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
   5 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2005); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEX (McArdle, 1993) and ORTEPIII (Burnett & Johnson, (1996); software used to prepare material for publication: CrystalStructure.

3-hydroxybenzamide

Crystal data

C7H7NO2	F(000) = 288.00
Mr = 137.14	Dx = 1.422 Mg m^−3
Monoclinic, P21/n	Melting point: 442 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71070 Å
a = 10.873 (5) Å	Cell parameters from 1547 reflections
b = 5.064 (2) Å	θ = 3.8–30.6°
c = 11.641 (5) Å	µ = 0.11 mm^−1
β = 92.414 (11)°	T = 293 K
V = 640.4 (5) Å^3	Prism, colorless
Z = 4	0.50 × 0.20 × 0.10 mm

Data collection

Rigaku Saturn diffractometer	1103 reflections with F^2 > 2σ(F^2)
Detector resolution: 7.31 pixels mm^-1	Rint = 0.023
ω scans	θmax = 30.7°
Absorption correction: multi-scan (Jacobson, 1998)	h = −14→14
Tmin = 0.938, Tmax = 0.989	k = −7→4
5804 measured reflections	l = −16→16
1707 independent reflections

Refinement

Refinement on F	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.046	Weighting scheme based on measured s.u.'s w = 1/σ^2(Fo)
wR(F^2) = 0.033	(Δ/σ)max < 0.001
S = 1.80	Δρmax = 0.23 e Å^−3
1103 reflections	Δρmin = −0.18 e Å^−3
119 parameters

Special details

Refinement. Refinement using reflections with F² > 2.0 σ(F²). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	1.02016 (12)	0.6332 (2)	0.31347 (10)	0.0437 (4)
O2	0.74569 (12)	0.5902 (2)	0.65295 (11)	0.0506 (4)
N1	1.00881 (17)	1.0577 (3)	0.25744 (13)	0.0449 (5)
C1	0.85187 (17)	0.7220 (3)	0.48475 (14)	0.0366 (5)
C2	0.75708 (17)	0.7528 (3)	0.55959 (14)	0.0378 (5)
C3	0.67116 (18)	0.9521 (3)	0.54101 (18)	0.0444 (6)
C4	0.68219 (19)	1.1214 (4)	0.44929 (18)	0.0474 (6)
C5	0.77896 (18)	1.0981 (3)	0.37602 (17)	0.0411 (5)
C6	0.86370 (14)	0.8957 (3)	0.39364 (13)	0.0332 (5)
C7	0.97042 (17)	0.8541 (3)	0.31871 (14)	0.0347 (5)
H1	0.9114 (14)	0.573 (3)	0.4945 (13)	0.043 (5)*
H3	0.6034 (16)	0.976 (3)	0.5965 (15)	0.053 (5)*
H4	0.6223 (16)	1.260 (3)	0.4369 (15)	0.053 (5)*
H5	0.7883 (16)	1.223 (3)	0.3118 (15)	0.054 (5)*
H6	0.819 (2)	0.484 (5)	0.668 (2)	0.132 (11)*
H7	0.9854 (17)	1.226 (3)	0.2698 (16)	0.060 (6)*
H8	1.0803 (19)	1.032 (4)	0.2176 (17)	0.072 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0485 (8)	0.0338 (7)	0.0499 (8)	0.0070 (6)	0.0150 (6)	0.0038 (5)
O2	0.0480 (9)	0.0546 (8)	0.0506 (8)	0.0062 (7)	0.0186 (7)	0.0153 (7)
N1	0.0538 (12)	0.0331 (9)	0.0493 (10)	0.0013 (8)	0.0180 (9)	0.0046 (8)
C1	0.0353 (11)	0.0355 (10)	0.0395 (11)	0.0040 (8)	0.0065 (9)	0.0030 (8)
C2	0.0358 (11)	0.0394 (10)	0.0388 (11)	−0.0018 (9)	0.0058 (9)	0.0010 (9)
C3	0.0353 (11)	0.0492 (12)	0.0493 (12)	0.0037 (10)	0.0091 (9)	−0.0036 (10)
C4	0.0400 (12)	0.0455 (12)	0.0566 (13)	0.0132 (10)	0.0022 (10)	0.0043 (10)
C5	0.0431 (12)	0.0390 (11)	0.0412 (12)	0.0034 (9)	0.0022 (9)	0.0041 (9)
C6	0.0320 (10)	0.0331 (9)	0.0346 (10)	−0.0008 (8)	0.0023 (8)	−0.0037 (8)
C7	0.0396 (11)	0.0326 (9)	0.0318 (10)	−0.0012 (8)	0.0017 (8)	−0.0010 (8)

Geometric parameters (Å, º)

O1—C7	1.245 (2)	C6—C7	1.496 (2)
O2—C2	1.373 (2)	O2—H6	0.97 (2)
N1—C7	1.331 (2)	N1—H7	0.904 (19)
C1—C2	1.386 (2)	N1—H8	0.93 (2)
C1—C6	1.388 (2)	C1—H1	0.997 (16)
C2—C3	1.386 (2)	C3—H3	1.007 (18)
C3—C4	1.379 (2)	C4—H4	0.963 (18)
C4—C5	1.387 (2)	C5—H5	0.988 (18)
C5—C6	1.388 (2)
C2—C1—C6	120.30 (16)	C2—O2—H6	112.3 (16)
O2—C2—C1	121.63 (16)	C7—N1—H7	123.3 (12)
O2—C2—C3	118.52 (16)	C7—N1—H8	116.5 (12)
C1—C2—C3	119.85 (16)	H7—N1—H8	117.2 (17)
C2—C3—C4	119.59 (18)	C2—C1—H1	120.6 (9)
C3—C4—C5	121.08 (18)	C6—C1—H1	119.0 (9)
C4—C5—C6	119.22 (17)	C2—C3—H3	119.6 (9)
C1—C6—C5	119.91 (16)	C4—C3—H3	120.7 (9)
C1—C6—C7	117.11 (14)	C3—C4—H4	119.2 (11)
C5—C6—C7	122.98 (15)	C5—C4—H4	119.7 (11)
O1—C7—N1	121.54 (17)	C4—C5—H5	121.0 (10)
O1—C7—C6	120.29 (15)	C6—C5—H5	119.8 (10)
N1—C7—C6	118.17 (15)
C2—C1—C6—C5	−1.2 (2)	C3—C4—C5—C6	2.0 (2)
C2—C1—C6—C7	178.29 (15)	C4—C5—C6—C1	−0.9 (2)
C6—C1—C2—O2	−177.53 (15)	C4—C5—C6—C7	179.62 (17)
C6—C1—C2—C3	2.3 (2)	C1—C6—C7—O1	23.1 (2)
O2—C2—C3—C4	178.59 (17)	C1—C6—C7—N1	−157.81 (16)
C1—C2—C3—C4	−1.2 (2)	C5—C6—C7—O1	−157.43 (17)
C2—C3—C4—C5	−0.9 (3)	C5—C6—C7—N1	21.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H8···O2^i	0.93 (2)	2.07 (2)	2.990 (2)	168 (2)
N1—H7···O1^ii	0.90 (2)	2.15 (2)	2.988 (2)	153 (2)
O2—H6···O1^iii	0.97 (2)	1.86 (2)	2.798 (2)	164 (2)

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