Buy article online - an online subscription or single-article purchase is required to access this article.
The coumarin system and the 2-hydroxybenzoyl group in the title compound, C
17H
12N
2O
5, are approximately coplanar. There are some intermolecular O—H
O hydrogen bonds and intramolecular N—H
O hydrogen bonds; the intermolecular O—H
O hydrogen bonds result in a chain along the
a axis.
Supporting information
CCDC reference: 608520
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.040
- wR factor = 0.120
- Data-to-parameter ratio = 14.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 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
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: TEXSAN (Molecular Structure Corporation, 1999); cell refinement: TEXSAN; data reduction: TEXSAN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: SHELXL97.
N'-(2-Hydroxybenzoyl)-2-oxo-2
H-chromene-3-carbohydrazide
top
Crystal data top
C17H12N2O5 | F(000) = 672 |
Mr = 324.29 | Dx = 1.485 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3321 reflections |
a = 9.467 (4) Å | θ = 3.0–27.5° |
b = 11.766 (4) Å | µ = 0.11 mm−1 |
c = 13.268 (7) Å | T = 293 K |
β = 100.96 (2)° | Block, yellow |
V = 1450.9 (11) Å3 | 0.60 × 0.25 × 0.15 mm |
Z = 4 | |
Data collection top
Rigaku Weissenberg IP diffractometer | 2401 reflections with I > 2σ(I) |
Radiation source: rotor traget | Rint = 0.028 |
Graphite monochromator | θmax = 27.5°, θmin = 3.0° |
ω scans | h = −10→12 |
14024 measured reflections | k = −15→15 |
3321 independent reflections | l = −17→17 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.120 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0742P)2] where P = (Fo2 + 2Fc2)/3 |
3321 reflections | (Δ/σ)max < 0.001 |
229 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
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 | Uiso*/Ueq | |
N1 | 0.30534 (11) | 0.50643 (8) | 0.52692 (8) | 0.0442 (3) | |
H1N | 0.3088 | 0.5822 | 0.5077 | 0.059 (4)* | |
N2 | 0.40952 (10) | 0.46588 (8) | 0.60539 (8) | 0.0431 (3) | |
H2N | 0.4019 | 0.3978 | 0.6251 | 0.063 (4)* | |
O1 | −0.00097 (10) | 0.64985 (7) | 0.29226 (7) | 0.0528 (3) | |
O2 | 0.18537 (12) | 0.67849 (8) | 0.41460 (9) | 0.0713 (3) | |
O3 | 0.18226 (10) | 0.34242 (7) | 0.51607 (8) | 0.0558 (3) | |
O4 | 0.49406 (10) | 0.64167 (7) | 0.62928 (8) | 0.0534 (3) | |
O5 | 0.51464 (10) | 0.31375 (7) | 0.74286 (8) | 0.0536 (3) | |
H5O | 0.5179 | 0.2536 | 0.7859 | 0.084 (6)* | |
C2 | 0.09776 (14) | 0.61077 (10) | 0.37315 (10) | 0.0475 (3) | |
C3 | 0.08839 (12) | 0.49143 (9) | 0.40143 (9) | 0.0387 (3) | |
C4 | −0.01890 (12) | 0.42627 (10) | 0.35067 (9) | 0.0406 (3) | |
H4 | −0.0256 | 0.3510 | 0.3706 | 0.047 (4)* | |
C5 | −0.23390 (14) | 0.40508 (12) | 0.21066 (11) | 0.0514 (3) | |
H5 | −0.2444 | 0.3292 | 0.2274 | 0.061 (4)* | |
C6 | −0.32744 (15) | 0.45291 (15) | 0.13090 (12) | 0.0623 (4) | |
H6 | −0.4022 | 0.4099 | 0.0940 | 0.070 (5)* | |
C7 | −0.31076 (16) | 0.56585 (15) | 0.10504 (12) | 0.0663 (4) | |
H7 | −0.3749 | 0.5977 | 0.0505 | 0.085 (6)* | |
C8 | −0.20170 (16) | 0.63156 (13) | 0.15817 (12) | 0.0581 (4) | |
H8 | −0.1904 | 0.7069 | 0.1399 | 0.069 (5)* | |
C9 | −0.10918 (13) | 0.58241 (11) | 0.23966 (10) | 0.0446 (3) | |
C10 | −0.12243 (12) | 0.46956 (10) | 0.26727 (9) | 0.0419 (3) | |
C11 | 0.19444 (12) | 0.43943 (9) | 0.48639 (9) | 0.0399 (3) | |
C12 | 0.50222 (12) | 0.54065 (10) | 0.65672 (10) | 0.0402 (3) | |
C13 | 0.61247 (12) | 0.49977 (10) | 0.74330 (9) | 0.0402 (3) | |
C14 | 0.61534 (12) | 0.39047 (10) | 0.78550 (10) | 0.0426 (3) | |
C15 | 0.72064 (14) | 0.36319 (12) | 0.86991 (11) | 0.0535 (3) | |
H15 | 0.7221 | 0.2912 | 0.8990 | 0.064 (4)* | |
C16 | 0.82278 (15) | 0.44200 (14) | 0.91084 (12) | 0.0628 (4) | |
H16 | 0.8934 | 0.4224 | 0.9669 | 0.074 (5)* | |
C17 | 0.82191 (15) | 0.55002 (14) | 0.86973 (12) | 0.0610 (4) | |
H17 | 0.8912 | 0.6031 | 0.8978 | 0.076 (5)* | |
C18 | 0.71743 (13) | 0.57765 (12) | 0.78710 (11) | 0.0507 (3) | |
H18 | 0.7164 | 0.6503 | 0.7594 | 0.061 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0440 (5) | 0.0404 (5) | 0.0436 (6) | −0.0021 (4) | −0.0034 (5) | 0.0023 (4) |
N2 | 0.0428 (5) | 0.0375 (5) | 0.0444 (6) | 0.0010 (4) | −0.0030 (4) | 0.0008 (4) |
O1 | 0.0603 (5) | 0.0444 (5) | 0.0482 (6) | −0.0044 (4) | −0.0036 (4) | 0.0088 (4) |
O2 | 0.0840 (7) | 0.0455 (5) | 0.0701 (7) | −0.0215 (5) | −0.0216 (6) | 0.0125 (5) |
O3 | 0.0608 (6) | 0.0399 (5) | 0.0595 (6) | −0.0046 (4) | −0.0065 (5) | 0.0067 (4) |
O4 | 0.0642 (6) | 0.0376 (4) | 0.0533 (6) | −0.0037 (4) | −0.0021 (4) | 0.0017 (4) |
O5 | 0.0553 (5) | 0.0387 (4) | 0.0592 (6) | −0.0025 (4) | −0.0088 (4) | 0.0044 (4) |
C2 | 0.0543 (7) | 0.0428 (6) | 0.0422 (7) | −0.0045 (5) | 0.0008 (6) | 0.0054 (5) |
C3 | 0.0416 (6) | 0.0386 (6) | 0.0354 (6) | −0.0005 (5) | 0.0056 (5) | −0.0007 (4) |
C4 | 0.0432 (6) | 0.0386 (6) | 0.0404 (7) | −0.0002 (5) | 0.0087 (5) | −0.0011 (5) |
C5 | 0.0465 (7) | 0.0600 (8) | 0.0468 (8) | −0.0034 (6) | 0.0068 (6) | −0.0117 (6) |
C6 | 0.0477 (7) | 0.0860 (11) | 0.0488 (9) | −0.0019 (7) | −0.0021 (6) | −0.0150 (8) |
C7 | 0.0559 (8) | 0.0936 (12) | 0.0442 (8) | 0.0142 (8) | −0.0037 (6) | 0.0013 (8) |
C8 | 0.0607 (8) | 0.0642 (9) | 0.0471 (8) | 0.0114 (7) | 0.0044 (6) | 0.0073 (6) |
C9 | 0.0458 (6) | 0.0496 (7) | 0.0379 (7) | 0.0026 (5) | 0.0067 (5) | −0.0005 (5) |
C10 | 0.0394 (6) | 0.0498 (6) | 0.0367 (6) | 0.0020 (5) | 0.0079 (5) | −0.0044 (5) |
C11 | 0.0429 (6) | 0.0371 (6) | 0.0389 (6) | −0.0006 (5) | 0.0060 (5) | −0.0026 (5) |
C12 | 0.0411 (6) | 0.0383 (6) | 0.0410 (7) | −0.0002 (5) | 0.0072 (5) | −0.0042 (5) |
C13 | 0.0363 (6) | 0.0435 (6) | 0.0402 (7) | 0.0018 (5) | 0.0058 (5) | −0.0050 (5) |
C14 | 0.0393 (6) | 0.0414 (6) | 0.0455 (7) | 0.0031 (5) | 0.0039 (5) | −0.0051 (5) |
C15 | 0.0509 (7) | 0.0545 (7) | 0.0511 (8) | 0.0086 (6) | −0.0008 (6) | 0.0029 (6) |
C16 | 0.0475 (7) | 0.0835 (10) | 0.0507 (9) | 0.0041 (7) | −0.0080 (6) | −0.0026 (7) |
C17 | 0.0466 (7) | 0.0741 (9) | 0.0567 (9) | −0.0131 (7) | −0.0045 (6) | −0.0076 (7) |
C18 | 0.0457 (7) | 0.0529 (7) | 0.0522 (8) | −0.0085 (6) | 0.0063 (6) | −0.0036 (6) |
Geometric parameters (Å, º) top
N1—C11 | 1.3410 (15) | C5—H5 | 0.9300 |
N1—N2 | 1.3763 (14) | C6—C7 | 1.389 (2) |
N1—H1N | 0.9297 | C6—H6 | 0.9300 |
N2—C12 | 1.3345 (15) | C7—C8 | 1.373 (2) |
N2—H2N | 0.8496 | C7—H7 | 0.9300 |
O1—C2 | 1.3622 (15) | C8—C9 | 1.3823 (19) |
O1—C9 | 1.3764 (15) | C8—H8 | 0.9300 |
O2—C2 | 1.2049 (15) | C9—C10 | 1.3894 (18) |
O3—C11 | 1.2200 (14) | C12—C13 | 1.4781 (17) |
O4—C12 | 1.2412 (15) | C13—C18 | 1.3948 (17) |
O5—C14 | 1.3559 (15) | C13—C14 | 1.4007 (17) |
O5—H5O | 0.9061 | C14—C15 | 1.3881 (19) |
C2—C3 | 1.4604 (17) | C15—C16 | 1.375 (2) |
C3—C4 | 1.3464 (16) | C15—H15 | 0.9300 |
C3—C11 | 1.4910 (16) | C16—C17 | 1.382 (2) |
C4—C10 | 1.4256 (17) | C16—H16 | 0.9300 |
C4—H4 | 0.9300 | C17—C18 | 1.369 (2) |
C5—C6 | 1.366 (2) | C17—H17 | 0.9300 |
C5—C10 | 1.3971 (17) | C18—H18 | 0.9300 |
| | | |
C11—N1—N2 | 119.57 (10) | O1—C9—C10 | 120.86 (11) |
C11—N1—H1N | 121.3 | C8—C9—C10 | 122.04 (12) |
N2—N1—H1N | 118.8 | C9—C10—C5 | 118.29 (12) |
C12—N2—N1 | 117.69 (10) | C9—C10—C4 | 117.57 (11) |
C12—N2—H2N | 123.4 | C5—C10—C4 | 124.12 (12) |
N1—N2—H2N | 118.0 | O3—C11—N1 | 122.37 (11) |
C2—O1—C9 | 122.55 (10) | O3—C11—C3 | 122.45 (10) |
C14—O5—H5O | 108.6 | N1—C11—C3 | 115.17 (10) |
O2—C2—O1 | 116.50 (11) | O4—C12—N2 | 118.91 (11) |
O2—C2—C3 | 126.06 (12) | O4—C12—C13 | 122.35 (11) |
O1—C2—C3 | 117.45 (11) | N2—C12—C13 | 118.74 (10) |
C4—C3—C2 | 119.73 (11) | C18—C13—C14 | 118.59 (11) |
C4—C3—C11 | 118.69 (10) | C18—C13—C12 | 116.87 (11) |
C2—C3—C11 | 121.58 (10) | C14—C13—C12 | 124.51 (10) |
C3—C4—C10 | 121.79 (11) | O5—C14—C15 | 121.52 (11) |
C3—C4—H4 | 119.1 | O5—C14—C13 | 119.06 (11) |
C10—C4—H4 | 119.1 | C15—C14—C13 | 119.42 (11) |
C6—C5—C10 | 120.35 (14) | C16—C15—C14 | 120.40 (13) |
C6—C5—H5 | 119.8 | C16—C15—H15 | 119.8 |
C10—C5—H5 | 119.8 | C14—C15—H15 | 119.8 |
C5—C6—C7 | 119.88 (14) | C15—C16—C17 | 120.88 (13) |
C5—C6—H6 | 120.1 | C15—C16—H16 | 119.6 |
C7—C6—H6 | 120.1 | C17—C16—H16 | 119.6 |
C8—C7—C6 | 121.45 (14) | C18—C17—C16 | 118.92 (13) |
C8—C7—H7 | 119.3 | C18—C17—H17 | 120.5 |
C6—C7—H7 | 119.3 | C16—C17—H17 | 120.5 |
C7—C8—C9 | 117.98 (14) | C17—C18—C13 | 121.79 (13) |
C7—C8—H8 | 121.0 | C17—C18—H18 | 119.1 |
C9—C8—H8 | 121.0 | C13—C18—H18 | 119.1 |
O1—C9—C8 | 117.09 (12) | | |
| | | |
C11—N1—N2—C12 | −167.44 (11) | N2—N1—C11—O3 | −0.5 (2) |
C9—O1—C2—O2 | −178.32 (12) | N2—N1—C11—C3 | −179.61 (10) |
C9—O1—C2—C3 | 1.89 (19) | C4—C3—C11—O3 | −4.97 (19) |
O2—C2—C3—C4 | 177.44 (14) | C2—C3—C11—O3 | 174.44 (12) |
O1—C2—C3—C4 | −2.79 (18) | C4—C3—C11—N1 | 174.14 (11) |
O2—C2—C3—C11 | −2.0 (2) | C2—C3—C11—N1 | −6.45 (17) |
O1—C2—C3—C11 | 177.81 (11) | N1—N2—C12—O4 | −2.70 (17) |
C2—C3—C4—C10 | 1.89 (18) | N1—N2—C12—C13 | 178.24 (11) |
C11—C3—C4—C10 | −178.69 (11) | O4—C12—C13—C18 | −6.32 (18) |
C10—C5—C6—C7 | 0.8 (2) | N2—C12—C13—C18 | 172.70 (11) |
C5—C6—C7—C8 | −0.1 (2) | O4—C12—C13—C14 | 171.58 (12) |
C6—C7—C8—C9 | −0.8 (2) | N2—C12—C13—C14 | −9.39 (19) |
C2—O1—C9—C8 | −179.26 (13) | C18—C13—C14—O5 | −179.35 (11) |
C2—O1—C9—C10 | −0.07 (19) | C12—C13—C14—O5 | 2.77 (19) |
C7—C8—C9—O1 | −179.70 (12) | C18—C13—C14—C15 | 0.80 (18) |
C7—C8—C9—C10 | 1.1 (2) | C12—C13—C14—C15 | −177.08 (12) |
O1—C9—C10—C5 | −179.63 (11) | O5—C14—C15—C16 | 179.08 (13) |
C8—C9—C10—C5 | −0.48 (19) | C13—C14—C15—C16 | −1.1 (2) |
O1—C9—C10—C4 | −0.92 (18) | C14—C15—C16—C17 | 0.7 (2) |
C8—C9—C10—C4 | 178.23 (12) | C15—C16—C17—C18 | −0.1 (2) |
C6—C5—C10—C9 | −0.50 (19) | C16—C17—C18—C13 | −0.2 (2) |
C6—C5—C10—C4 | −179.11 (13) | C14—C13—C18—C17 | −0.2 (2) |
C3—C4—C10—C9 | −0.05 (18) | C12—C13—C18—C17 | 177.87 (13) |
C3—C4—C10—C5 | 178.58 (11) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5O···O4i | 0.91 | 1.75 | 2.6527 (15) | 174 |
N1—H1N···O2 | 0.93 | 1.90 | 2.6392 (15) | 134 |
N2—H2N···O5 | 0.85 | 1.98 | 2.6135 (15) | 131 |
Symmetry code: (i) −x+1, y−1/2, −z+3/2. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.