Isoquinoline-1-carboxylic acid

Jing, L.-H.; Feng, Y.; Qin, D.-B.; Gu, S.-J.; Zhang, H.-X.

doi:10.1107/S160053680702658X

Isoquinoline-1-carboxylic acid

L.-H. Jing, Y. Feng, D.-B. Qin, S.-J. Gu and H.-X. Zhang

The title compound, C₁₀H₇NO₂, crystallizes with three molecules in the asymmetric unit; these are linked by O—H

N hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680702658X/bt2386sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680702658X/bt2386Isup2.hkl Contains datablock I

CCDC reference: 654875

checkCIF report

Key indicators

Single-crystal X-ray study
T = 153 K
Mean (C-C) = 0.002 Å
R factor = 0.050
wR factor = 0.134
Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        200 Deg.
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.07 Ratio
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.08
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.38
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

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

   1 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
   2 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

Comment top

Non-covalent interactions, such as hydrogen bonding, π-π stacking and C—H···π interactions, play a dominant role in supramolecular self-assembly (Casnati et al., 2003; Ghosh & Bharadwaj, 2004; Glidewell et al., 2005; Jennings et al., 2001). In order to further understand supramolecular self-assembly through non-covalent interactions, we have synthesized the title compound following a published procedure (Padbury and Lindwall, 1945). It is used as a material in the synthesis of organic metal compounds (You & Park, 2005; Kwon et al., 2005; Carlton & Molapisi, 2000; Smith et al., 1995).

Bond lengths and angles in (I) are normal. Compound (I) crystallizes in the triclinic space group P-1 with Z'=3. In (I), the three isoquinoline rings in the asymmetric unit are approximately planar, with maximum deviations of -0.014 (7) Å for atom C1 in N1/C1—C9 ring, 0.017 (6) Å for atom C2A in N1A/C1A—C9A ring and 0.022 (6) Å for atom C6B in N1B/C1B—C9B ring (Fig. 1). The torsion angles between the pyridine rings and carboxyl groups of three molecules in asymmetric unit are different. The N1—C1—C10—O1 torsion angle is -13.3 (2)°. However, the N1A—C1A—C10A—O1A and N1B—C1B—C10B—O1B are 36.17 (19) and -34.1 (2)°, respectively. The crystal packing is stabilized by O—H···N hydrogen bonds (Table 1).

Related literature top

For related literature, see: Carlton & Molapisi (2000); Casnati et al. (2003); Ghosh & Bharadwaj (2004); Glidewell et al. (2005); Jennings et al. (2001); Kwon et al. (2005); Padbury & Lindwall (1945); Smith et al. (1995); You & Park (2005).

Experimental top

The title compound was prepared following a published procedure (Padbury and Lindwall, 1945). Colorless single crystals suitable for X-ray diffraction were obtained by recrystallization from dimethylsulfoxide.

Structure description top

Computing details top

Data collection: RAPID-AUTO (Rigaku/MSC, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. The molecular structure of the title compound showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Isoquinoline-1-carboxylic acid top

Crystal data top

C₁₀H₇NO₂	Z = 6
M_r = 173.17	F(000) = 540
Triclinic, P1	D_x = 1.476 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3707 (6) Å	Cell parameters from 9042 reflections
b = 11.4278 (7) Å	θ = 3.1–27.6°
c = 13.2044 (10) Å	µ = 0.11 mm⁻¹
α = 108.957 (2)°	T = 153 K
β = 100.674 (2)°	Block, colorless
γ = 91.447 (2)°	0.58 × 0.52 × 0.34 mm
V = 1168.97 (14) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	4016 reflections with I > 2σ(I)
Radiation source: Rotating Anode	R_int = 0.037
Graphite monochromator	θ_max = 27.5°, θ_min = 3.2°
ω scans	h = −10→10
11161 measured reflections	k = −14→14
5223 independent reflections	l = −17→17

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)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.135	w = 1/[σ²(F_o²) + (0.0708P)² + 0.33P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
5223 reflections	Δρ_max = 0.52 e Å⁻³
365 parameters	Δρ_min = −0.31 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.018 (3)

Crystal data top

C₁₀H₇NO₂	γ = 91.447 (2)°
M_r = 173.17	V = 1168.97 (14) Å³
Triclinic, P1	Z = 6
a = 8.3707 (6) Å	Mo Kα radiation
b = 11.4278 (7) Å	µ = 0.11 mm⁻¹
c = 13.2044 (10) Å	T = 153 K
α = 108.957 (2)°	0.58 × 0.52 × 0.34 mm
β = 100.674 (2)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4016 reflections with I > 2σ(I)
11161 measured reflections	R_int = 0.037
5223 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.52 e Å⁻³
5223 reflections	Δρ_min = −0.31 e Å⁻³
365 parameters

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
O1	0.55014 (15)	0.22987 (10)	0.47803 (9)	0.0308 (3)
O2	0.44813 (17)	0.08212 (11)	0.31984 (9)	0.0403 (3)
N1	0.32740 (16)	0.37701 (11)	0.44770 (10)	0.0228 (3)
C1	0.33565 (18)	0.27907 (13)	0.36107 (11)	0.0197 (3)
C2	0.2212 (2)	0.46223 (14)	0.43699 (13)	0.0279 (4)
H2	0.2178	0.5322	0.4995	0.034*
C3	0.1195 (2)	0.45160 (14)	0.34056 (13)	0.0272 (3)
H3	0.0460	0.5127	0.3366	0.033*
C4	0.0189 (2)	0.33229 (15)	0.14450 (13)	0.0278 (3)
H4	−0.0574	0.3910	0.1385	0.033*
C5	0.0266 (2)	0.23220 (15)	0.05484 (12)	0.0297 (4)
H5	−0.0442	0.2218	−0.0132	0.036*
C6	0.1387 (2)	0.14449 (14)	0.06288 (12)	0.0271 (3)
H6	0.1433	0.0757	−0.0003	0.033*
C7	0.24126 (19)	0.15637 (14)	0.15988 (12)	0.0236 (3)
H7	0.3161	0.0960	0.1636	0.028*
C8	0.23623 (18)	0.25916 (13)	0.25556 (11)	0.0195 (3)
C9	0.12432 (19)	0.34902 (14)	0.24652 (12)	0.0224 (3)
C10	0.45201 (18)	0.18691 (13)	0.38325 (11)	0.0206 (3)
O1A	0.67121 (14)	0.22924 (10)	0.70186 (9)	0.0300 (3)
O2A	0.93960 (16)	0.25229 (11)	0.76675 (11)	0.0482 (4)
C1A	0.82048 (18)	0.06951 (13)	0.61722 (11)	0.0205 (3)
N1A	0.71612 (15)	0.05087 (11)	0.52356 (10)	0.0208 (3)
C2A	0.70952 (19)	−0.05813 (14)	0.43994 (12)	0.0238 (3)
H2A	0.6328	−0.0714	0.3736	0.029*
C3A	0.80874 (19)	−0.14899 (13)	0.44770 (12)	0.0240 (3)
H3A	0.8011	−0.2236	0.3874	0.029*
C4A	1.0295 (2)	−0.22249 (14)	0.55853 (12)	0.0264 (3)
H4A	1.0271	−0.2972	0.4991	0.032*
C5A	1.1356 (2)	−0.20353 (15)	0.65542 (13)	0.0285 (4)
H5A	1.2068	−0.2648	0.6632	0.034*
C6A	1.1395 (2)	−0.09298 (15)	0.74413 (13)	0.0280 (3)
H6A	1.2132	−0.0810	0.8114	0.034*
C7A	1.03937 (19)	−0.00292 (14)	0.73495 (12)	0.0249 (3)
H7A	1.0435	0.0707	0.7957	0.030*
C8A	0.92890 (18)	−0.01916 (13)	0.63473 (11)	0.0198 (3)
C9A	0.92297 (18)	−0.13159 (13)	0.54586 (12)	0.0213 (3)
C10A	0.81768 (19)	0.19380 (14)	0.70422 (12)	0.0237 (3)
O1B	0.50385 (15)	0.43664 (11)	0.65072 (9)	0.0333 (3)
O2B	0.28869 (16)	0.51262 (15)	0.71761 (10)	0.0535 (4)
N1B	0.65308 (16)	0.44696 (11)	0.84876 (10)	0.0223 (3)
C1B	0.54342 (18)	0.52634 (13)	0.83991 (11)	0.0207 (3)
C2B	0.75794 (19)	0.46784 (14)	0.94605 (12)	0.0244 (3)
H2B	0.8360	0.4101	0.9513	0.029*
C3B	0.75569 (19)	0.56808 (14)	1.03629 (12)	0.0245 (3)
H3B	0.8303	0.5790	1.1030	0.029*
C4B	0.6351 (2)	0.76283 (14)	1.12033 (12)	0.0278 (3)
H4B	0.7078	0.7764	1.1883	0.033*
C5B	0.5253 (2)	0.84668 (14)	1.11053 (13)	0.0322 (4)
H5B	0.5205	0.9176	1.1719	0.039*
C6B	0.4187 (2)	0.82810 (15)	1.00929 (14)	0.0320 (4)
H6B	0.3443	0.8880	1.0029	0.038*
C7B	0.4205 (2)	0.72551 (14)	0.92027 (13)	0.0268 (3)
H7B	0.3474	0.7145	0.8530	0.032*
C8B	0.53150 (18)	0.63544 (13)	0.92817 (11)	0.0203 (3)
C9B	0.64159 (19)	0.65562 (13)	1.02982 (12)	0.0217 (3)
C10B	0.43012 (19)	0.49211 (13)	0.72890 (12)	0.0244 (3)
H1O	0.608 (4)	0.170 (3)	0.493 (2)	0.086 (9)*
H1OA	0.674 (3)	0.312 (3)	0.755 (2)	0.074 (8)*
H1OB	0.431 (3)	0.413 (3)	0.580 (2)	0.080 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0374 (7)	0.0281 (6)	0.0188 (5)	0.0141 (5)	−0.0048 (5)	0.0020 (4)
O2	0.0531 (8)	0.0296 (6)	0.0243 (6)	0.0214 (6)	−0.0087 (5)	−0.0019 (5)
N1	0.0252 (7)	0.0221 (6)	0.0172 (6)	0.0071 (5)	0.0017 (5)	0.0026 (5)
C1	0.0207 (7)	0.0207 (6)	0.0165 (7)	0.0039 (6)	0.0032 (5)	0.0046 (5)
C2	0.0332 (9)	0.0239 (7)	0.0210 (7)	0.0095 (6)	0.0025 (6)	0.0011 (6)
C3	0.0293 (8)	0.0235 (7)	0.0266 (8)	0.0115 (6)	0.0026 (6)	0.0066 (6)
C4	0.0298 (8)	0.0303 (8)	0.0236 (8)	0.0086 (7)	0.0006 (6)	0.0117 (6)
C5	0.0326 (9)	0.0376 (9)	0.0163 (7)	0.0038 (7)	−0.0023 (6)	0.0096 (6)
C6	0.0343 (9)	0.0281 (7)	0.0158 (7)	0.0039 (7)	0.0040 (6)	0.0036 (6)
C7	0.0282 (8)	0.0241 (7)	0.0173 (7)	0.0063 (6)	0.0043 (6)	0.0051 (6)
C8	0.0210 (7)	0.0202 (7)	0.0165 (7)	0.0026 (6)	0.0037 (5)	0.0053 (5)
C9	0.0233 (7)	0.0242 (7)	0.0188 (7)	0.0038 (6)	0.0025 (6)	0.0068 (6)
C10	0.0231 (7)	0.0224 (7)	0.0153 (7)	0.0058 (6)	0.0028 (5)	0.0055 (5)
O1A	0.0294 (6)	0.0263 (6)	0.0252 (6)	0.0099 (5)	0.0014 (5)	−0.0019 (4)
O2A	0.0341 (7)	0.0336 (6)	0.0495 (8)	0.0101 (6)	−0.0102 (6)	−0.0128 (6)
C1A	0.0216 (7)	0.0222 (7)	0.0163 (7)	0.0033 (6)	0.0031 (5)	0.0050 (5)
N1A	0.0230 (6)	0.0218 (6)	0.0163 (6)	0.0056 (5)	0.0028 (5)	0.0051 (5)
C2A	0.0265 (8)	0.0263 (7)	0.0152 (7)	0.0041 (6)	0.0020 (6)	0.0035 (6)
C3A	0.0302 (8)	0.0220 (7)	0.0157 (7)	0.0042 (6)	0.0046 (6)	0.0007 (5)
C4A	0.0338 (9)	0.0240 (7)	0.0221 (7)	0.0092 (7)	0.0093 (6)	0.0063 (6)
C5A	0.0298 (8)	0.0318 (8)	0.0300 (8)	0.0133 (7)	0.0088 (6)	0.0162 (7)
C6A	0.0286 (8)	0.0347 (8)	0.0214 (8)	0.0059 (7)	0.0011 (6)	0.0124 (6)
C7A	0.0280 (8)	0.0275 (7)	0.0174 (7)	0.0045 (6)	0.0021 (6)	0.0063 (6)
C8A	0.0220 (7)	0.0208 (6)	0.0167 (7)	0.0044 (6)	0.0050 (5)	0.0058 (5)
C9A	0.0241 (8)	0.0224 (7)	0.0190 (7)	0.0060 (6)	0.0075 (6)	0.0072 (6)
C10A	0.0264 (8)	0.0230 (7)	0.0188 (7)	0.0079 (6)	0.0007 (6)	0.0047 (6)
O1B	0.0325 (6)	0.0445 (7)	0.0147 (5)	0.0103 (5)	0.0023 (5)	−0.0003 (5)
O2B	0.0323 (7)	0.0808 (11)	0.0255 (7)	0.0235 (7)	−0.0029 (5)	−0.0080 (7)
N1B	0.0263 (7)	0.0217 (6)	0.0162 (6)	0.0054 (5)	0.0040 (5)	0.0028 (5)
C1B	0.0230 (7)	0.0216 (7)	0.0150 (7)	0.0032 (6)	0.0041 (5)	0.0027 (5)
C2B	0.0270 (8)	0.0245 (7)	0.0205 (7)	0.0075 (6)	0.0021 (6)	0.0072 (6)
C3B	0.0290 (8)	0.0256 (7)	0.0154 (7)	0.0032 (6)	−0.0006 (6)	0.0052 (6)
C4B	0.0342 (9)	0.0270 (7)	0.0161 (7)	0.0028 (7)	0.0022 (6)	0.0005 (6)
C5B	0.0414 (10)	0.0245 (7)	0.0227 (8)	0.0064 (7)	0.0080 (7)	−0.0040 (6)
C6B	0.0356 (9)	0.0265 (8)	0.0305 (9)	0.0134 (7)	0.0072 (7)	0.0038 (6)
C7B	0.0289 (8)	0.0264 (7)	0.0214 (7)	0.0082 (6)	0.0031 (6)	0.0036 (6)
C8B	0.0231 (7)	0.0204 (6)	0.0151 (7)	0.0037 (6)	0.0038 (5)	0.0027 (5)
C9B	0.0250 (8)	0.0216 (7)	0.0161 (7)	0.0019 (6)	0.0041 (6)	0.0032 (5)
C10B	0.0286 (8)	0.0231 (7)	0.0159 (7)	0.0059 (6)	0.0014 (6)	0.0003 (5)

Geometric parameters (Å, º) top

O1—C10	1.2967 (17)	C4A—C5A	1.364 (2)
O1—H1O	0.90 (3)	C4A—C9A	1.417 (2)
O2—C10	1.2136 (17)	C4A—H4A	0.9500
N1—C1	1.3293 (18)	C5A—C6A	1.411 (2)
N1—C2	1.3583 (19)	C5A—H5A	0.9500
C1—C8	1.4284 (19)	C6A—C7A	1.365 (2)
C1—C10	1.5133 (19)	C6A—H6A	0.9500
C2—C3	1.361 (2)	C7A—C8A	1.4210 (19)
C2—H2	0.9500	C7A—H7A	0.9500
C3—C9	1.412 (2)	C8A—C9A	1.4233 (19)
C3—H3	0.9500	O1B—C10B	1.2957 (18)
C4—C5	1.366 (2)	O1B—H1OB	0.97 (3)
C4—C9	1.419 (2)	O2B—C10B	1.204 (2)
C4—H4	0.9500	N1B—C1B	1.3230 (19)
C5—C6	1.406 (2)	N1B—C2B	1.3602 (18)
C5—H5	0.9500	C1B—C8B	1.4241 (18)
C6—C7	1.367 (2)	C1B—C10B	1.5149 (19)
C6—H6	0.9500	C2B—C3B	1.362 (2)
C7—C8	1.4268 (19)	C2B—H2B	0.9500
C7—H7	0.9500	C3B—C9B	1.412 (2)
C8—C9	1.426 (2)	C3B—H3B	0.9500
O1A—C10A	1.2990 (18)	C4B—C5B	1.364 (2)
O1A—H1OA	0.97 (3)	C4B—C9B	1.4171 (19)
O2A—C10A	1.2103 (19)	C4B—H4B	0.9500
C1A—N1A	1.3256 (18)	C5B—C6B	1.411 (2)
C1A—C8A	1.423 (2)	C5B—H5B	0.9500
C1A—C10A	1.5131 (19)	C6B—C7B	1.367 (2)
N1A—C2A	1.3617 (18)	C6B—H6B	0.9500
C2A—C3A	1.364 (2)	C7B—C8B	1.420 (2)
C2A—H2A	0.9500	C7B—H7B	0.9500
C3A—C9A	1.413 (2)	C8B—C9B	1.4261 (19)
C3A—H3A	0.9500

C10—O1—H1O	111.1 (19)	C6A—C5A—H5A	119.9
C1—N1—C2	119.62 (12)	C7A—C6A—C5A	121.17 (14)
N1—C1—C8	122.42 (13)	C7A—C6A—H6A	119.4
N1—C1—C10	115.25 (12)	C5A—C6A—H6A	119.4
C8—C1—C10	122.27 (12)	C6A—C7A—C8A	120.13 (14)
N1—C2—C3	122.81 (13)	C6A—C7A—H7A	119.9
N1—C2—H2	118.6	C8A—C7A—H7A	119.9
C3—C2—H2	118.6	C7A—C8A—C1A	124.19 (13)
C2—C3—C9	119.41 (13)	C7A—C8A—C9A	118.68 (13)
C2—C3—H3	120.3	C1A—C8A—C9A	117.12 (13)
C9—C3—H3	120.3	C3A—C9A—C4A	122.19 (13)
C5—C4—C9	120.37 (14)	C3A—C9A—C8A	118.37 (13)
C5—C4—H4	119.8	C4A—C9A—C8A	119.43 (13)
C9—C4—H4	119.8	O2A—C10A—O1A	125.12 (13)
C4—C5—C6	120.28 (14)	O2A—C10A—C1A	122.87 (13)
C4—C5—H5	119.9	O1A—C10A—C1A	112.00 (13)
C6—C5—H5	119.9	C10B—O1B—H1OB	111.6 (16)
C7—C6—C5	121.24 (14)	C1B—N1B—C2B	119.50 (12)
C7—C6—H6	119.4	N1B—C1B—C8B	122.68 (13)
C5—C6—H6	119.4	N1B—C1B—C10B	115.00 (12)
C6—C7—C8	120.18 (14)	C8B—C1B—C10B	122.31 (12)
C6—C7—H7	119.9	N1B—C2B—C3B	122.76 (13)
C8—C7—H7	119.9	N1B—C2B—H2B	118.6
C9—C8—C7	118.35 (13)	C3B—C2B—H2B	118.6
C9—C8—C1	116.99 (12)	C2B—C3B—C9B	119.44 (13)
C7—C8—C1	124.66 (13)	C2B—C3B—H3B	120.3
C3—C9—C4	121.69 (13)	C9B—C3B—H3B	120.3
C3—C9—C8	118.74 (13)	C5B—C4B—C9B	120.47 (14)
C4—C9—C8	119.56 (13)	C5B—C4B—H4B	119.8
O2—C10—O1	124.09 (13)	C9B—C4B—H4B	119.8
O2—C10—C1	122.74 (13)	C4B—C5B—C6B	120.07 (14)
O1—C10—C1	113.12 (12)	C4B—C5B—H5B	120.0
C10A—O1A—H1OA	110.1 (16)	C6B—C5B—H5B	120.0
N1A—C1A—C8A	122.96 (13)	C7B—C6B—C5B	121.20 (14)
N1A—C1A—C10A	114.79 (12)	C7B—C6B—H6B	119.4
C8A—C1A—C10A	122.25 (12)	C5B—C6B—H6B	119.4
C1A—N1A—C2A	119.29 (12)	C6B—C7B—C8B	120.16 (14)
C3A—C2A—N1A	122.55 (13)	C6B—C7B—H7B	119.9
C3A—C2A—H2A	118.7	C8B—C7B—H7B	119.9
N1A—C2A—H2A	118.7	C7B—C8B—C1B	124.23 (13)
C2A—C3A—C9A	119.68 (13)	C7B—C8B—C9B	118.61 (13)
C2A—C3A—H3A	120.2	C1B—C8B—C9B	117.14 (12)
C9A—C3A—H3A	120.2	C3B—C9B—C4B	122.06 (14)
C5A—C4A—C9A	120.47 (14)	C3B—C9B—C8B	118.46 (13)
C5A—C4A—H4A	119.8	C4B—C9B—C8B	119.47 (13)
C9A—C4A—H4A	119.8	O2B—C10B—O1B	125.65 (14)
C4A—C5A—C6A	120.10 (14)	O2B—C10B—C1B	122.81 (14)
C4A—C5A—H5A	119.9	O1B—C10B—C1B	111.52 (13)

C2—N1—C1—C8	0.0 (2)	C2A—C3A—C9A—C4A	−179.77 (14)
C2—N1—C1—C10	−177.20 (14)	C2A—C3A—C9A—C8A	0.9 (2)
C1—N1—C2—C3	0.8 (3)	C5A—C4A—C9A—C3A	−178.48 (15)
N1—C2—C3—C9	−0.8 (3)	C5A—C4A—C9A—C8A	0.9 (2)
C9—C4—C5—C6	0.2 (3)	C7A—C8A—C9A—C3A	177.78 (14)
C4—C5—C6—C7	0.5 (3)	C1A—C8A—C9A—C3A	−1.3 (2)
C5—C6—C7—C8	−0.1 (2)	C7A—C8A—C9A—C4A	−1.6 (2)
C6—C7—C8—C9	−1.0 (2)	C1A—C8A—C9A—C4A	179.34 (14)
C6—C7—C8—C1	178.80 (15)	N1A—C1A—C10A—O2A	−142.98 (17)
N1—C1—C8—C9	−0.7 (2)	C8A—C1A—C10A—O2A	36.1 (2)
C10—C1—C8—C9	176.28 (13)	N1A—C1A—C10A—O1A	36.12 (19)
N1—C1—C8—C7	179.43 (14)	C8A—C1A—C10A—O1A	−144.80 (15)
C10—C1—C8—C7	−3.6 (2)	C2B—N1B—C1B—C8B	1.1 (2)
C2—C3—C9—C4	178.82 (16)	C2B—N1B—C1B—C10B	−178.41 (13)
C2—C3—C9—C8	0.0 (2)	C1B—N1B—C2B—C3B	0.0 (2)
C5—C4—C9—C3	179.88 (16)	N1B—C2B—C3B—C9B	−0.6 (2)
C5—C4—C9—C8	−1.3 (2)	C9B—C4B—C5B—C6B	−1.0 (3)
C7—C8—C9—C3	−179.45 (14)	C4B—C5B—C6B—C7B	1.4 (3)
C1—C8—C9—C3	0.7 (2)	C5B—C6B—C7B—C8B	−0.4 (3)
C7—C8—C9—C4	1.7 (2)	C6B—C7B—C8B—C1B	−179.46 (15)
C1—C8—C9—C4	−178.14 (14)	C6B—C7B—C8B—C9B	−1.0 (2)
N1—C1—C10—O2	163.91 (15)	N1B—C1B—C8B—C7B	176.98 (15)
C8—C1—C10—O2	−13.3 (2)	C10B—C1B—C8B—C7B	−3.5 (2)
N1—C1—C10—O1	−13.4 (2)	N1B—C1B—C8B—C9B	−1.5 (2)
C8—C1—C10—O1	169.42 (14)	C10B—C1B—C8B—C9B	178.01 (14)
C8A—C1A—N1A—C2A	0.8 (2)	C2B—C3B—C9B—C4B	−178.90 (15)
C10A—C1A—N1A—C2A	179.85 (13)	C2B—C3B—C9B—C8B	0.2 (2)
C1A—N1A—C2A—C3A	−1.3 (2)	C5B—C4B—C9B—C3B	178.75 (16)
N1A—C2A—C3A—C9A	0.4 (2)	C5B—C4B—C9B—C8B	−0.3 (2)
C9A—C4A—C5A—C6A	0.2 (3)	C7B—C8B—C9B—C3B	−177.78 (14)
C4A—C5A—C6A—C7A	−0.5 (3)	C1B—C8B—C9B—C3B	0.8 (2)
C5A—C6A—C7A—C8A	−0.2 (3)	C7B—C8B—C9B—C4B	1.3 (2)
C6A—C7A—C8A—C1A	−179.72 (15)	C1B—C8B—C9B—C4B	179.92 (14)
C6A—C7A—C8A—C9A	1.3 (2)	N1B—C1B—C10B—O2B	144.38 (17)
N1A—C1A—C8A—C7A	−178.52 (14)	C8B—C1B—C10B—O2B	−35.2 (2)
C10A—C1A—C8A—C7A	2.5 (2)	N1B—C1B—C10B—O1B	−34.05 (19)
N1A—C1A—C8A—C9A	0.5 (2)	C8B—C1B—C10B—O1B	146.41 (15)
C10A—C1A—C8A—C9A	−178.52 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1A	0.91 (3)	1.76 (3)	2.6673 (16)	177 (3)
O1A—H1OA···N1B	0.97 (3)	1.68 (3)	2.6407 (16)	172 (2)
O1B—H1OB···N1	0.99 (3)	1.69 (3)	2.6715 (17)	171 (3)

Experimental details

Crystal data
Chemical formula	C₁₀H₇NO₂
M_r	173.17
Crystal system, space group	Triclinic, P1
Temperature (K)	153
a, b, c (Å)	8.3707 (6), 11.4278 (7), 13.2044 (10)
α, β, γ (°)	108.957 (2), 100.674 (2), 91.447 (2)
V (Å³)	1168.97 (14)
Z	6
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.58 × 0.52 × 0.34

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11161, 5223, 4016
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.135, 1.02
No. of reflections	5223
No. of parameters	365
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.31

Computer programs: RAPID-AUTO (Rigaku/MSC, 2004), RAPID-AUTO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP in SHELXTL (Bruker, 1997), SHELXL97.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1A	0.91 (3)	1.76 (3)	2.6673 (16)	177 (3)
O1A—H1OA···N1B	0.97 (3)	1.68 (3)	2.6407 (16)	172 (2)
O1B—H1OB···N1	0.99 (3)	1.69 (3)	2.6715 (17)	171 (3)

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