Isoquinoline 1-oxide–2-nitro­benzoic acid (1/1)

The title mol­ecular complex, C₉H₇NO·C₇H₅NO₄, owes its formation to an inter­molecular hydrogen bond between the O—H and N—O groups, with an O...O distance of 2.514 (2) Å. The dihedral angle between the planes of the isoquinoline N-oxide and nitro­benzoic acid rings of the complex is 49.91 (4)°. The crystal structure exhibits overlap between the aromatic rings of the mol­ecules in the [101] direction.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.040
• wR factor = 0.104
• Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O4     -   HO4    ...       1.03 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1995); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

(I)

Crystal data

C9H7NO·C7H5NO4	F(000) = 648
Mr = 312.28	Dx = 1.441 Mg m^−3
Monoclinic, P21/c	Melting point: 387(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.639 (3) Å	Cell parameters from 25 reflections
b = 7.235 (4) Å	θ = 1.0–25.0°
c = 17.206 (3) Å	µ = 0.11 mm^−1
β = 96.399 (18)°	T = 293 K
V = 1439.9 (9) Å^3	Prism, pale-yellow
Z = 4	0.23 × 0.20 × 0.12 mm

Data collection

Rigaku AFC-7S diffractometer	θmax = 25.0°, θmin = 1.8°
Radiation source: fine-focus X-ray sealed tube	h = 0→13
Graphite monochromator	k = 0→8
ω/2θ scans	l = −20→20
2532 measured reflections	2 standard reflections every 150 min
2532 independent reflections	intensity decay: none
1847 reflections with I > 2σ(I)

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)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.104	w = 1/[σ^2(Fo^2) + (0.0367P)^2 + 0.6379P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
2532 reflections	Δρmax = 0.18 e Å^−3
213 parameters	Δρmin = −0.16 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0214 (15)

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.

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

	x	y	z	Uiso*/Ueq
O1	0.40744 (12)	0.1866 (2)	0.22580 (8)	0.0465 (4)
N1	0.48582 (14)	0.1614 (2)	0.17589 (10)	0.0367 (4)
C8	0.49669 (17)	−0.0030 (3)	0.14362 (12)	0.0380 (5)
H8	0.4485	−0.0990	0.1556	0.046*
C9	0.57919 (17)	−0.0354 (3)	0.09174 (11)	0.0359 (5)
C16	0.55663 (17)	0.3065 (3)	0.16014 (12)	0.0420 (5)
H16	0.5485	0.4208	0.1836	0.050*
C14	0.65181 (17)	0.1123 (3)	0.07356 (12)	0.0386 (5)
C15	0.63738 (18)	0.2825 (3)	0.11095 (13)	0.0430 (5)
H15	0.6851	0.3811	0.1014	0.052*
C10	0.58902 (19)	−0.2097 (3)	0.05616 (13)	0.0455 (5)
H10	0.5420	−0.3072	0.0681	0.055*
C13	0.73171 (18)	0.0807 (3)	0.01953 (13)	0.0489 (6)
H13	0.7800	0.1758	0.0068	0.059*
C12	0.7387 (2)	−0.0885 (4)	−0.01425 (14)	0.0548 (6)
H12	0.7916	−0.1075	−0.0502	0.066*
C11	0.6677 (2)	−0.2342 (3)	0.00431 (13)	0.0522 (6)
H11	0.6744	−0.3491	−0.0191	0.063*
O4	0.24361 (14)	0.4142 (2)	0.20581 (11)	0.0579 (5)
HO4	0.315 (3)	0.330 (5)	0.2080 (19)	0.109 (12)*
N2	0.01858 (18)	0.4717 (3)	0.10164 (12)	0.0547 (5)
C2	0.04442 (18)	0.6520 (3)	0.13718 (12)	0.0399 (5)
C1	0.15747 (17)	0.6985 (3)	0.16543 (12)	0.0373 (5)
C7	0.25856 (17)	0.5686 (3)	0.16991 (13)	0.0413 (5)
C6	0.17605 (19)	0.8761 (3)	0.19298 (13)	0.0454 (6)
H6	0.2506	0.9122	0.2120	0.054*
C5	0.0867 (2)	1.0021 (3)	0.19299 (14)	0.0518 (6)
H5	0.1016	1.1215	0.2114	0.062*
C4	−0.0242 (2)	0.9506 (3)	0.16577 (15)	0.0554 (6)
H4	−0.0846	1.0346	0.1664	0.066*
C3	−0.04582 (19)	0.7751 (3)	0.13765 (14)	0.0508 (6)
H3	−0.1207	0.7396	0.1191	0.061*
O5	0.34724 (14)	0.6113 (2)	0.14451 (13)	0.0738 (6)
O2	0.08988 (17)	0.4029 (3)	0.06384 (12)	0.0775 (6)
O3	−0.07481 (17)	0.4013 (3)	0.10961 (14)	0.0884 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0473 (8)	0.0438 (9)	0.0507 (9)	0.0115 (7)	0.0158 (7)	0.0054 (7)
N1	0.0353 (9)	0.0337 (10)	0.0405 (9)	0.0034 (7)	0.0022 (8)	0.0010 (8)
C8	0.0371 (11)	0.0323 (11)	0.0437 (12)	−0.0013 (9)	0.0006 (9)	0.0041 (10)
C9	0.0340 (10)	0.0349 (11)	0.0371 (11)	0.0031 (9)	−0.0033 (9)	0.0037 (9)
C16	0.0438 (12)	0.0312 (11)	0.0495 (13)	−0.0020 (10)	−0.0006 (10)	−0.0045 (10)
C14	0.0343 (11)	0.0374 (12)	0.0430 (11)	0.0011 (9)	−0.0011 (9)	0.0037 (10)
C15	0.0395 (11)	0.0365 (12)	0.0522 (13)	−0.0067 (10)	0.0018 (10)	0.0028 (10)
C10	0.0500 (13)	0.0346 (12)	0.0506 (13)	0.0021 (10)	−0.0002 (11)	−0.0014 (10)
C13	0.0390 (12)	0.0537 (15)	0.0548 (14)	0.0013 (11)	0.0088 (10)	0.0084 (12)
C12	0.0531 (14)	0.0635 (17)	0.0493 (13)	0.0171 (13)	0.0130 (11)	0.0048 (13)
C11	0.0623 (15)	0.0445 (13)	0.0488 (13)	0.0148 (12)	0.0024 (12)	−0.0050 (11)
O4	0.0437 (9)	0.0492 (10)	0.0831 (12)	0.0100 (8)	0.0178 (8)	0.0239 (9)
N2	0.0501 (12)	0.0435 (12)	0.0669 (14)	−0.0001 (10)	−0.0104 (10)	−0.0021 (10)
C2	0.0399 (11)	0.0363 (12)	0.0428 (12)	−0.0004 (9)	0.0012 (9)	0.0037 (10)
C1	0.0352 (11)	0.0352 (11)	0.0425 (11)	−0.0005 (9)	0.0080 (9)	0.0054 (10)
C7	0.0349 (11)	0.0383 (12)	0.0504 (13)	−0.0023 (10)	0.0040 (10)	0.0000 (10)
C6	0.0404 (12)	0.0398 (13)	0.0558 (14)	−0.0038 (10)	0.0053 (10)	−0.0014 (11)
C5	0.0620 (15)	0.0373 (12)	0.0575 (14)	0.0023 (12)	0.0135 (12)	−0.0037 (11)
C4	0.0536 (14)	0.0469 (15)	0.0670 (16)	0.0150 (12)	0.0122 (12)	0.0072 (12)
C3	0.0380 (12)	0.0495 (14)	0.0633 (15)	0.0049 (11)	−0.0013 (11)	0.0071 (12)
O5	0.0439 (10)	0.0509 (11)	0.1322 (17)	0.0026 (8)	0.0348 (11)	0.0183 (11)
O2	0.0697 (12)	0.0662 (13)	0.0938 (14)	0.0141 (10)	−0.0032 (11)	−0.0316 (11)
O3	0.0646 (12)	0.0676 (14)	0.1300 (18)	−0.0276 (11)	−0.0027 (12)	−0.0100 (13)

Geometric parameters (Å, º)

O1—N1	1.333 (2)	O4—C7	1.297 (3)
N1—C8	1.325 (3)	O4—HO4	1.03 (3)
N1—C16	1.380 (3)	N2—O2	1.216 (2)
C8—C9	1.402 (3)	N2—O3	1.222 (3)
C8—H8	0.9300	N2—C2	1.458 (3)
C9—C10	1.412 (3)	C2—C3	1.378 (3)
C9—C14	1.419 (3)	C2—C1	1.392 (3)
C16—C15	1.344 (3)	C1—C6	1.378 (3)
C16—H16	0.9300	C1—C7	1.501 (3)
C14—C13	1.405 (3)	C7—O5	1.205 (2)
C14—C15	1.408 (3)	C7—O4	1.297 (3)
C15—H15	0.9300	C6—C5	1.383 (3)
C10—C11	1.359 (3)	C6—H6	0.9300
C10—H10	0.9300	C5—C4	1.374 (3)
C13—C12	1.361 (3)	C5—H5	0.9300
C13—H13	0.9300	C4—C3	1.372 (3)
C12—C11	1.399 (3)	C4—H4	0.9300
C12—H12	0.9300	C3—H3	0.9300
C11—H11	0.9300
C8—N1—O1	119.79 (17)	C10—C11—H11	119.7
C8—N1—C16	120.90 (18)	C12—C11—H11	119.7
O1—N1—C16	119.29 (17)	C7—O4—HO4	112.4 (18)
N1—C8—C9	121.42 (19)	O2—N2—O3	123.9 (2)
N1—C8—H8	119.3	O2—N2—C2	118.0 (2)
C9—C8—H8	119.3	O3—N2—C2	118.1 (2)
C8—C9—C10	121.31 (19)	C3—C2—C1	122.2 (2)
C8—C9—C14	118.79 (19)	C3—C2—N2	117.33 (19)
C10—C9—C14	119.9 (2)	C1—C2—N2	120.36 (19)
C15—C16—N1	120.0 (2)	C6—C1—C2	116.82 (19)
C15—C16—H16	120.0	C6—C1—C7	118.30 (19)
N1—C16—H16	120.0	C2—C1—C7	124.86 (19)
C13—C14—C15	124.5 (2)	O5—C7—O4	124.0 (2)
C13—C14—C9	118.5 (2)	O5—C7—C1	121.3 (2)
C15—C14—C9	116.97 (19)	O4—C7—C1	114.67 (18)
C16—C15—C14	121.9 (2)	C1—C6—C5	121.7 (2)
C16—C15—H15	119.1	C1—C6—H6	119.2
C14—C15—H15	119.1	C5—C6—H6	119.2
C11—C10—C9	119.6 (2)	C4—C5—C6	119.9 (2)
C11—C10—H10	120.2	C4—C5—H5	120.0
C9—C10—H10	120.2	C6—C5—H5	120.0
C12—C13—C14	120.3 (2)	C3—C4—C5	120.0 (2)
C12—C13—H13	119.8	C3—C4—H4	120.0
C14—C13—H13	119.8	C5—C4—H4	120.0
C13—C12—C11	121.0 (2)	C4—C3—C2	119.4 (2)
C13—C12—H12	119.5	C4—C3—H3	120.3
C11—C12—H12	119.5	C2—C3—H3	120.3
C10—C11—C12	120.7 (2)
O1—N1—C8—C9	−179.10 (17)	O2—N2—C2—C3	142.0 (2)
C16—N1—C8—C9	−0.8 (3)	O3—N2—C2—C3	−35.8 (3)
N1—C8—C9—C10	−178.69 (19)	O2—N2—C2—C1	−34.7 (3)
N1—C8—C9—C14	−0.3 (3)	O3—N2—C2—C1	147.4 (2)
C8—N1—C16—C15	0.6 (3)	C3—C2—C1—C6	−1.2 (3)
O1—N1—C16—C15	178.91 (18)	N2—C2—C1—C6	175.42 (19)
C8—C9—C14—C13	−177.91 (18)	C3—C2—C1—C7	177.1 (2)
C10—C9—C14—C13	0.5 (3)	N2—C2—C1—C7	−6.3 (3)
C8—C9—C14—C15	1.5 (3)	C6—C1—C7—O5	−51.5 (3)
C10—C9—C14—C15	179.88 (19)	C2—C1—C7—O5	130.2 (2)
N1—C16—C15—C14	0.7 (3)	C6—C1—C7—O4	125.5 (2)
C13—C14—C15—C16	177.6 (2)	C2—C1—C7—O4	−52.7 (3)
C9—C14—C15—C16	−1.7 (3)	C2—C1—C6—C5	0.3 (3)
C8—C9—C10—C11	178.0 (2)	C7—C1—C6—C5	−178.0 (2)
C14—C9—C10—C11	−0.4 (3)	C1—C6—C5—C4	0.7 (4)
C15—C14—C13—C12	−179.4 (2)	C6—C5—C4—C3	−0.9 (4)
C9—C14—C13—C12	−0.1 (3)	C5—C4—C3—C2	0.1 (4)
C14—C13—C12—C11	−0.5 (3)	C1—C2—C3—C4	0.9 (3)
C9—C10—C11—C12	−0.1 (3)	N2—C2—C3—C4	−175.7 (2)
C13—C12—C11—C10	0.6 (4)