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The coumarin system and the 2-hydroxy­benzoyl group in the title compound, C17H12N2O5, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806014656/wk2009sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806014656/wk2009Isup2.hkl
Contains datablock I

CCDC reference: 608520

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.040
  • wR factor = 0.120
  • Data-to-parameter ratio = 14.5

checkCIF/PLATON results

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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

Computing details top

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-2H-chromene-3-carbohydrazide top
Crystal data top
C17H12N2O5F(000) = 672
Mr = 324.29Dx = 1.485 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3321 reflections
a = 9.467 (4) Åθ = 3.0–27.5°
b = 11.766 (4) ŵ = 0.11 mm1
c = 13.268 (7) ÅT = 293 K
β = 100.96 (2)°Block, yellow
V = 1450.9 (11) Å30.60 × 0.25 × 0.15 mm
Z = 4
Data collection top
Rigaku Weissenberg IP
diffractometer
2401 reflections with I > 2σ(I)
Radiation source: rotor tragetRint = 0.028
Graphite monochromatorθmax = 27.5°, θmin = 3.0°
ω scansh = 1012
14024 measured reflectionsk = 1515
3321 independent reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H 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 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.25 e Å3
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
xyzUiso*/Ueq
N10.30534 (11)0.50643 (8)0.52692 (8)0.0442 (3)
H1N0.30880.58220.50770.059 (4)*
N20.40952 (10)0.46588 (8)0.60539 (8)0.0431 (3)
H2N0.40190.39780.62510.063 (4)*
O10.00097 (10)0.64985 (7)0.29226 (7)0.0528 (3)
O20.18537 (12)0.67849 (8)0.41460 (9)0.0713 (3)
O30.18226 (10)0.34242 (7)0.51607 (8)0.0558 (3)
O40.49406 (10)0.64167 (7)0.62928 (8)0.0534 (3)
O50.51464 (10)0.31375 (7)0.74286 (8)0.0536 (3)
H5O0.51790.25360.78590.084 (6)*
C20.09776 (14)0.61077 (10)0.37315 (10)0.0475 (3)
C30.08839 (12)0.49143 (9)0.40143 (9)0.0387 (3)
C40.01890 (12)0.42627 (10)0.35067 (9)0.0406 (3)
H40.02560.35100.37060.047 (4)*
C50.23390 (14)0.40508 (12)0.21066 (11)0.0514 (3)
H50.24440.32920.22740.061 (4)*
C60.32744 (15)0.45291 (15)0.13090 (12)0.0623 (4)
H60.40220.40990.09400.070 (5)*
C70.31076 (16)0.56585 (15)0.10504 (12)0.0663 (4)
H70.37490.59770.05050.085 (6)*
C80.20170 (16)0.63156 (13)0.15817 (12)0.0581 (4)
H80.19040.70690.13990.069 (5)*
C90.10918 (13)0.58241 (11)0.23966 (10)0.0446 (3)
C100.12243 (12)0.46956 (10)0.26727 (9)0.0419 (3)
C110.19444 (12)0.43943 (9)0.48639 (9)0.0399 (3)
C120.50222 (12)0.54065 (10)0.65672 (10)0.0402 (3)
C130.61247 (12)0.49977 (10)0.74330 (9)0.0402 (3)
C140.61534 (12)0.39047 (10)0.78550 (10)0.0426 (3)
C150.72064 (14)0.36319 (12)0.86991 (11)0.0535 (3)
H150.72210.29120.89900.064 (4)*
C160.82278 (15)0.44200 (14)0.91084 (12)0.0628 (4)
H160.89340.42240.96690.074 (5)*
C170.82191 (15)0.55002 (14)0.86973 (12)0.0610 (4)
H170.89120.60310.89780.076 (5)*
C180.71743 (13)0.57765 (12)0.78710 (11)0.0507 (3)
H180.71640.65030.75940.061 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0440 (5)0.0404 (5)0.0436 (6)0.0021 (4)0.0034 (5)0.0023 (4)
N20.0428 (5)0.0375 (5)0.0444 (6)0.0010 (4)0.0030 (4)0.0008 (4)
O10.0603 (5)0.0444 (5)0.0482 (6)0.0044 (4)0.0036 (4)0.0088 (4)
O20.0840 (7)0.0455 (5)0.0701 (7)0.0215 (5)0.0216 (6)0.0125 (5)
O30.0608 (6)0.0399 (5)0.0595 (6)0.0046 (4)0.0065 (5)0.0067 (4)
O40.0642 (6)0.0376 (4)0.0533 (6)0.0037 (4)0.0021 (4)0.0017 (4)
O50.0553 (5)0.0387 (4)0.0592 (6)0.0025 (4)0.0088 (4)0.0044 (4)
C20.0543 (7)0.0428 (6)0.0422 (7)0.0045 (5)0.0008 (6)0.0054 (5)
C30.0416 (6)0.0386 (6)0.0354 (6)0.0005 (5)0.0056 (5)0.0007 (4)
C40.0432 (6)0.0386 (6)0.0404 (7)0.0002 (5)0.0087 (5)0.0011 (5)
C50.0465 (7)0.0600 (8)0.0468 (8)0.0034 (6)0.0068 (6)0.0117 (6)
C60.0477 (7)0.0860 (11)0.0488 (9)0.0019 (7)0.0021 (6)0.0150 (8)
C70.0559 (8)0.0936 (12)0.0442 (8)0.0142 (8)0.0037 (6)0.0013 (8)
C80.0607 (8)0.0642 (9)0.0471 (8)0.0114 (7)0.0044 (6)0.0073 (6)
C90.0458 (6)0.0496 (7)0.0379 (7)0.0026 (5)0.0067 (5)0.0005 (5)
C100.0394 (6)0.0498 (6)0.0367 (6)0.0020 (5)0.0079 (5)0.0044 (5)
C110.0429 (6)0.0371 (6)0.0389 (6)0.0006 (5)0.0060 (5)0.0026 (5)
C120.0411 (6)0.0383 (6)0.0410 (7)0.0002 (5)0.0072 (5)0.0042 (5)
C130.0363 (6)0.0435 (6)0.0402 (7)0.0018 (5)0.0058 (5)0.0050 (5)
C140.0393 (6)0.0414 (6)0.0455 (7)0.0031 (5)0.0039 (5)0.0051 (5)
C150.0509 (7)0.0545 (7)0.0511 (8)0.0086 (6)0.0008 (6)0.0029 (6)
C160.0475 (7)0.0835 (10)0.0507 (9)0.0041 (7)0.0080 (6)0.0026 (7)
C170.0466 (7)0.0741 (9)0.0567 (9)0.0131 (7)0.0045 (6)0.0076 (7)
C180.0457 (7)0.0529 (7)0.0522 (8)0.0085 (6)0.0063 (6)0.0036 (6)
Geometric parameters (Å, º) top
N1—C111.3410 (15)C5—H50.9300
N1—N21.3763 (14)C6—C71.389 (2)
N1—H1N0.9297C6—H60.9300
N2—C121.3345 (15)C7—C81.373 (2)
N2—H2N0.8496C7—H70.9300
O1—C21.3622 (15)C8—C91.3823 (19)
O1—C91.3764 (15)C8—H80.9300
O2—C21.2049 (15)C9—C101.3894 (18)
O3—C111.2200 (14)C12—C131.4781 (17)
O4—C121.2412 (15)C13—C181.3948 (17)
O5—C141.3559 (15)C13—C141.4007 (17)
O5—H5O0.9061C14—C151.3881 (19)
C2—C31.4604 (17)C15—C161.375 (2)
C3—C41.3464 (16)C15—H150.9300
C3—C111.4910 (16)C16—C171.382 (2)
C4—C101.4256 (17)C16—H160.9300
C4—H40.9300C17—C181.369 (2)
C5—C61.366 (2)C17—H170.9300
C5—C101.3971 (17)C18—H180.9300
C11—N1—N2119.57 (10)O1—C9—C10120.86 (11)
C11—N1—H1N121.3C8—C9—C10122.04 (12)
N2—N1—H1N118.8C9—C10—C5118.29 (12)
C12—N2—N1117.69 (10)C9—C10—C4117.57 (11)
C12—N2—H2N123.4C5—C10—C4124.12 (12)
N1—N2—H2N118.0O3—C11—N1122.37 (11)
C2—O1—C9122.55 (10)O3—C11—C3122.45 (10)
C14—O5—H5O108.6N1—C11—C3115.17 (10)
O2—C2—O1116.50 (11)O4—C12—N2118.91 (11)
O2—C2—C3126.06 (12)O4—C12—C13122.35 (11)
O1—C2—C3117.45 (11)N2—C12—C13118.74 (10)
C4—C3—C2119.73 (11)C18—C13—C14118.59 (11)
C4—C3—C11118.69 (10)C18—C13—C12116.87 (11)
C2—C3—C11121.58 (10)C14—C13—C12124.51 (10)
C3—C4—C10121.79 (11)O5—C14—C15121.52 (11)
C3—C4—H4119.1O5—C14—C13119.06 (11)
C10—C4—H4119.1C15—C14—C13119.42 (11)
C6—C5—C10120.35 (14)C16—C15—C14120.40 (13)
C6—C5—H5119.8C16—C15—H15119.8
C10—C5—H5119.8C14—C15—H15119.8
C5—C6—C7119.88 (14)C15—C16—C17120.88 (13)
C5—C6—H6120.1C15—C16—H16119.6
C7—C6—H6120.1C17—C16—H16119.6
C8—C7—C6121.45 (14)C18—C17—C16118.92 (13)
C8—C7—H7119.3C18—C17—H17120.5
C6—C7—H7119.3C16—C17—H17120.5
C7—C8—C9117.98 (14)C17—C18—C13121.79 (13)
C7—C8—H8121.0C17—C18—H18119.1
C9—C8—H8121.0C13—C18—H18119.1
O1—C9—C8117.09 (12)
C11—N1—N2—C12167.44 (11)N2—N1—C11—O30.5 (2)
C9—O1—C2—O2178.32 (12)N2—N1—C11—C3179.61 (10)
C9—O1—C2—C31.89 (19)C4—C3—C11—O34.97 (19)
O2—C2—C3—C4177.44 (14)C2—C3—C11—O3174.44 (12)
O1—C2—C3—C42.79 (18)C4—C3—C11—N1174.14 (11)
O2—C2—C3—C112.0 (2)C2—C3—C11—N16.45 (17)
O1—C2—C3—C11177.81 (11)N1—N2—C12—O42.70 (17)
C2—C3—C4—C101.89 (18)N1—N2—C12—C13178.24 (11)
C11—C3—C4—C10178.69 (11)O4—C12—C13—C186.32 (18)
C10—C5—C6—C70.8 (2)N2—C12—C13—C18172.70 (11)
C5—C6—C7—C80.1 (2)O4—C12—C13—C14171.58 (12)
C6—C7—C8—C90.8 (2)N2—C12—C13—C149.39 (19)
C2—O1—C9—C8179.26 (13)C18—C13—C14—O5179.35 (11)
C2—O1—C9—C100.07 (19)C12—C13—C14—O52.77 (19)
C7—C8—C9—O1179.70 (12)C18—C13—C14—C150.80 (18)
C7—C8—C9—C101.1 (2)C12—C13—C14—C15177.08 (12)
O1—C9—C10—C5179.63 (11)O5—C14—C15—C16179.08 (13)
C8—C9—C10—C50.48 (19)C13—C14—C15—C161.1 (2)
O1—C9—C10—C40.92 (18)C14—C15—C16—C170.7 (2)
C8—C9—C10—C4178.23 (12)C15—C16—C17—C180.1 (2)
C6—C5—C10—C90.50 (19)C16—C17—C18—C130.2 (2)
C6—C5—C10—C4179.11 (13)C14—C13—C18—C170.2 (2)
C3—C4—C10—C90.05 (18)C12—C13—C18—C17177.87 (13)
C3—C4—C10—C5178.58 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5O···O4i0.911.752.6527 (15)174
N1—H1N···O20.931.902.6392 (15)134
N2—H2N···O50.851.982.6135 (15)131
Symmetry code: (i) x+1, y1/2, z+3/2.
 

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