Download citation
Download citation
link to html
The structure of the title compound, C25H22ClN3O2·C2H6O, displays N—H...O, O—H...O, O—H...N, C—H...Cl, C—H...O hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806010956/at2021sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806010956/at2021Isup2.hkl
Contains datablock I

CCDC reference: 604961

Key indicators

  • Single-crystal X-ray study
  • T = 208 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.061
  • wR factor = 0.159
  • Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.09 PLAT414_ALERT_2_C Short Intra D-H..H-X H2A .. H19 .. 1.99 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C2 H6 O
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SIR2004 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

4-Dimethylaminobenzoic(4-chloro-2-phenyl-2H-chromen-3-ylmethylene)hydrazide top
Crystal data top
C25H22ClN3O2·C2H6OZ = 2
Mr = 477.97F(000) = 504
Triclinic, P1Dx = 1.330 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.710 (2) ÅCell parameters from 5716 reflections
b = 10.668 (2) Åθ = 2.6–28.1°
c = 12.002 (3) ŵ = 0.20 mm1
α = 78.409 (3)°T = 208 K
β = 88.988 (3)°Rod, yellow
γ = 78.532 (3)°0.15 × 0.15 × 0.10 mm
V = 1193.3 (4) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
4200 independent reflections
Radiation source: fine-focus sealed tube3233 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.070
φ and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
h = 1111
Tmin = 0.971, Tmax = 0.981k = 1212
12114 measured reflectionsl = 1414
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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0855P)2]
where P = (Fo2 + 2Fc2)/3
4200 reflections(Δ/σ)max < 0.001
311 parametersΔρmax = 0.45 e Å3
0 restraintsΔρmin = 0.22 e Å3
Special details top

Experimental. Spectroscopic analysis, 1H NMR (300 MHz, DMSO-d6, δ, p.p.m.): 11.796 (s, 1H), 8.785 (s, 1H), 7.764 (d, 2H, J = 7.5 Hz), 7.564 (d, 1H, J = 7.8 Hz), 7.338–7.262 (m, 6H), 7.049 (t, 1H, J = 7.8 Hz), 6.932 (d, 1H, J = 8.1 Hz), 6.723(d, 2H, J = 7.5 Hz), 6.562 (s, 1H).

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
C10.4135 (3)0.3721 (3)0.2067 (2)0.0372 (7)
H10.34740.36810.15190.045*
C20.3825 (3)0.4654 (3)0.2727 (3)0.0425 (7)
H20.29610.52500.26250.051*
C30.4781 (3)0.4706 (3)0.3531 (2)0.0434 (7)
H30.45670.53390.39850.052*
C40.6058 (3)0.3841 (2)0.3685 (2)0.0366 (7)
H40.67020.38780.42470.044*
C50.6383 (3)0.2925 (2)0.3014 (2)0.0300 (6)
C60.5417 (3)0.2834 (2)0.2200 (2)0.0296 (6)
C70.5884 (3)0.1890 (2)0.1489 (2)0.0290 (6)
C80.7118 (3)0.1048 (2)0.1663 (2)0.0271 (6)
C90.8011 (3)0.0992 (2)0.2685 (2)0.0278 (6)
H90.89990.08780.24400.033*
C100.7649 (3)0.0178 (2)0.0909 (2)0.0292 (6)
H100.71210.01840.02580.035*
C110.7926 (3)0.0138 (2)0.3661 (2)0.0245 (5)
C120.9134 (3)0.0790 (2)0.4253 (2)0.0340 (6)
H121.00020.05890.40030.041*
C130.9092 (3)0.1744 (3)0.5218 (2)0.0424 (7)
H130.99250.21830.56250.051*
C140.7821 (3)0.2040 (3)0.5574 (2)0.0435 (7)
H140.77820.26730.62370.052*
C150.6616 (3)0.1423 (3)0.4972 (2)0.0389 (7)
H150.57550.16520.52080.047*
C160.6656 (3)0.0461 (3)0.4014 (2)0.0318 (6)
H160.58220.00280.36050.038*
C171.0453 (3)0.2287 (2)0.0526 (2)0.0291 (6)
C181.0726 (3)0.3156 (2)0.0296 (2)0.0276 (6)
C190.9728 (3)0.3256 (2)0.1073 (2)0.0319 (6)
H190.88290.27200.11070.038*
C201.0028 (3)0.4121 (3)0.1790 (2)0.0348 (6)
H200.93330.41570.23120.042*
C211.1337 (3)0.4946 (2)0.1763 (2)0.0317 (6)
C221.2345 (3)0.4857 (2)0.0972 (2)0.0325 (6)
H221.32400.54020.09260.039*
C231.2033 (3)0.3980 (2)0.0264 (2)0.0295 (6)
H231.27240.39360.02570.035*
C241.2890 (3)0.6818 (3)0.2307 (3)0.0484 (8)
H24A1.37200.64340.23530.073*
H24B1.29200.73400.28850.073*
H24C1.28620.73670.15610.073*
C251.0625 (4)0.5834 (3)0.3334 (3)0.0560 (9)
H25A0.99050.62760.29690.084*
H25B1.10870.63040.38950.084*
H25C1.01970.49510.37060.084*
C261.3118 (4)0.1533 (3)0.3478 (3)0.0565 (9)
H26A1.26300.10920.40470.085*
H26B1.40850.18970.37290.085*
H26C1.26570.22300.33730.085*
C271.3092 (3)0.0594 (4)0.2394 (3)0.0570 (9)
H27A1.35170.01280.25190.068*
H27B1.36710.10270.18500.068*
N10.8839 (2)0.06028 (19)0.11241 (17)0.0298 (5)
N20.9233 (2)0.13719 (19)0.03471 (17)0.0295 (5)
H2A0.87130.12800.02580.035*
N31.1647 (3)0.5791 (2)0.2490 (2)0.0432 (6)
O10.77051 (18)0.21885 (16)0.31231 (15)0.0325 (4)
O21.1249 (2)0.23724 (18)0.13272 (16)0.0392 (5)
O31.1736 (2)0.00782 (18)0.19112 (17)0.0447 (5)
H3A1.13830.06790.17710.067*
Cl10.47936 (8)0.19501 (7)0.03381 (6)0.0429 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0309 (15)0.0380 (15)0.0422 (16)0.0049 (12)0.0036 (12)0.0091 (13)
C20.0400 (17)0.0350 (16)0.0488 (18)0.0019 (13)0.0079 (14)0.0099 (14)
C30.058 (2)0.0328 (15)0.0385 (17)0.0029 (14)0.0129 (15)0.0125 (13)
C40.0487 (18)0.0295 (14)0.0323 (15)0.0065 (13)0.0025 (13)0.0093 (12)
C50.0327 (15)0.0241 (13)0.0317 (14)0.0056 (11)0.0069 (11)0.0026 (11)
C60.0335 (15)0.0270 (13)0.0276 (14)0.0068 (11)0.0065 (11)0.0034 (11)
C70.0301 (14)0.0288 (13)0.0275 (14)0.0069 (11)0.0001 (11)0.0032 (11)
C80.0305 (14)0.0243 (13)0.0258 (13)0.0055 (11)0.0029 (11)0.0035 (10)
C90.0290 (14)0.0251 (13)0.0285 (14)0.0026 (11)0.0042 (11)0.0068 (11)
C100.0316 (15)0.0295 (13)0.0258 (14)0.0047 (11)0.0007 (11)0.0056 (11)
C110.0281 (14)0.0216 (12)0.0250 (13)0.0020 (10)0.0010 (10)0.0107 (10)
C120.0321 (15)0.0315 (14)0.0394 (16)0.0065 (12)0.0011 (12)0.0094 (12)
C130.0454 (18)0.0351 (15)0.0421 (17)0.0029 (13)0.0131 (14)0.0008 (13)
C140.063 (2)0.0358 (15)0.0301 (15)0.0132 (15)0.0025 (14)0.0017 (12)
C150.0406 (17)0.0451 (16)0.0335 (15)0.0160 (14)0.0082 (13)0.0070 (13)
C160.0284 (15)0.0332 (14)0.0325 (15)0.0034 (11)0.0003 (11)0.0062 (11)
C170.0332 (15)0.0238 (13)0.0304 (14)0.0056 (11)0.0028 (12)0.0063 (11)
C180.0303 (14)0.0212 (12)0.0309 (14)0.0054 (11)0.0029 (11)0.0042 (10)
C190.0290 (15)0.0280 (13)0.0379 (15)0.0019 (11)0.0014 (12)0.0085 (12)
C200.0355 (16)0.0353 (15)0.0351 (15)0.0078 (12)0.0032 (12)0.0096 (12)
C210.0398 (16)0.0248 (13)0.0308 (14)0.0087 (12)0.0061 (12)0.0045 (11)
C220.0331 (15)0.0253 (13)0.0364 (16)0.0032 (11)0.0036 (12)0.0031 (11)
C230.0362 (15)0.0243 (13)0.0265 (13)0.0038 (11)0.0009 (11)0.0036 (10)
C240.061 (2)0.0321 (15)0.0535 (19)0.0022 (15)0.0058 (16)0.0194 (14)
C250.069 (2)0.054 (2)0.051 (2)0.0051 (17)0.0014 (17)0.0313 (16)
C260.052 (2)0.058 (2)0.055 (2)0.0050 (17)0.0154 (16)0.0044 (17)
C270.049 (2)0.072 (2)0.048 (2)0.0137 (17)0.0081 (16)0.0042 (17)
N10.0358 (13)0.0265 (11)0.0269 (12)0.0046 (10)0.0033 (10)0.0067 (9)
N20.0336 (13)0.0288 (11)0.0259 (11)0.0018 (10)0.0012 (9)0.0097 (9)
N30.0505 (16)0.0393 (13)0.0424 (14)0.0024 (12)0.0011 (12)0.0205 (11)
O10.0349 (11)0.0262 (9)0.0371 (10)0.0027 (8)0.0039 (8)0.0108 (8)
O20.0426 (12)0.0376 (10)0.0366 (11)0.0008 (9)0.0089 (9)0.0137 (9)
O30.0516 (13)0.0385 (11)0.0425 (12)0.0053 (10)0.0155 (10)0.0068 (9)
Cl10.0423 (4)0.0450 (4)0.0386 (4)0.0047 (3)0.0123 (3)0.0136 (3)
Geometric parameters (Å, º) top
C1—C21.378 (4)C17—O21.223 (3)
C1—C61.396 (4)C17—N21.366 (3)
C1—H10.9400C17—C181.471 (3)
C2—C31.368 (4)C18—C231.389 (3)
C2—H20.9400C18—C191.390 (4)
C3—C41.381 (4)C19—C201.372 (4)
C3—H30.9400C19—H190.9400
C4—C51.374 (4)C20—C211.392 (4)
C4—H40.9400C20—H200.9400
C5—O11.359 (3)C21—N31.365 (3)
C5—C61.396 (4)C21—C221.406 (4)
C6—C71.448 (4)C22—C231.373 (4)
C7—C81.339 (4)C22—H220.9400
C7—Cl11.739 (3)C23—H230.9400
C8—C101.442 (3)C24—N31.446 (4)
C8—C91.499 (3)C24—H24A0.9700
C9—O11.451 (3)C24—H24B0.9700
C9—C111.516 (3)C24—H24C0.9700
C9—H90.9900C25—N31.444 (4)
C10—N11.279 (3)C25—H25A0.9700
C10—H100.9400C25—H25B0.9700
C11—C121.368 (4)C25—H25C0.9700
C11—C161.382 (3)C26—C271.472 (4)
C12—C131.385 (4)C26—H26A0.9700
C12—H120.9400C26—H26B0.9700
C13—C141.375 (4)C26—H26C0.9700
C13—H130.9400C27—O31.408 (4)
C14—C151.362 (4)C27—H27A0.9800
C14—H140.9400C27—H27B0.9800
C15—C161.385 (4)N1—N21.364 (3)
C15—H150.9400N2—H2A0.8700
C16—H160.9400O3—H3A0.8300
C2—C1—C6120.9 (3)N2—C17—C18115.7 (2)
C2—C1—H1119.5C23—C18—C19117.4 (2)
C6—C1—H1119.5C23—C18—C17118.6 (2)
C3—C2—C1119.6 (3)C19—C18—C17123.9 (2)
C3—C2—H2120.2C20—C19—C18121.3 (2)
C1—C2—H2120.2C20—C19—H19119.3
C2—C3—C4120.8 (3)C18—C19—H19119.3
C2—C3—H3119.6C19—C20—C21121.5 (2)
C4—C3—H3119.6C19—C20—H20119.3
C5—C4—C3119.8 (3)C21—C20—H20119.3
C5—C4—H4120.1N3—C21—C20121.6 (2)
C3—C4—H4120.1N3—C21—C22121.0 (2)
O1—C5—C4117.1 (2)C20—C21—C22117.3 (2)
O1—C5—C6122.1 (2)C23—C22—C21120.5 (2)
C4—C5—C6120.6 (2)C23—C22—H22119.8
C5—C6—C1118.2 (2)C21—C22—H22119.8
C5—C6—C7116.6 (2)C22—C23—C18122.0 (2)
C1—C6—C7125.0 (2)C22—C23—H23119.0
C8—C7—C6122.6 (2)C18—C23—H23119.0
C8—C7—Cl1120.8 (2)N3—C24—H24A109.5
C6—C7—Cl1116.56 (19)N3—C24—H24B109.5
C7—C8—C10123.2 (2)H24A—C24—H24B109.5
C7—C8—C9119.3 (2)N3—C24—H24C109.5
C10—C8—C9117.4 (2)H24A—C24—H24C109.5
O1—C9—C8112.87 (19)H24B—C24—H24C109.5
O1—C9—C11108.06 (19)N3—C25—H25A109.5
C8—C9—C11114.3 (2)N3—C25—H25B109.5
O1—C9—H9107.1H25A—C25—H25B109.5
C8—C9—H9107.1N3—C25—H25C109.5
C11—C9—H9107.1H25A—C25—H25C109.5
N1—C10—C8120.0 (2)H25B—C25—H25C109.5
N1—C10—H10120.0C27—C26—H26A109.5
C8—C10—H10120.0C27—C26—H26B109.5
C12—C11—C16119.5 (2)H26A—C26—H26B109.5
C12—C11—C9118.6 (2)C27—C26—H26C109.5
C16—C11—C9121.8 (2)H26A—C26—H26C109.5
C11—C12—C13120.7 (3)H26B—C26—H26C109.5
C11—C12—H12119.6O3—C27—C26114.0 (3)
C13—C12—H12119.6O3—C27—H27A108.7
C14—C13—C12119.3 (3)C26—C27—H27A108.7
C14—C13—H13120.3O3—C27—H27B108.7
C12—C13—H13120.3C26—C27—H27B108.7
C15—C14—C13120.4 (3)H27A—C27—H27B107.6
C15—C14—H14119.8C10—N1—N2114.7 (2)
C13—C14—H14119.8N1—N2—C17119.5 (2)
C14—C15—C16120.2 (3)N1—N2—H2A120.3
C14—C15—H15119.9C17—N2—H2A120.3
C16—C15—H15119.9C21—N3—C25120.6 (2)
C11—C16—C15119.8 (3)C21—N3—C24120.8 (2)
C11—C16—H16120.1C25—N3—C24117.6 (2)
C15—C16—H16120.1C5—O1—C9119.80 (19)
O2—C17—N2121.4 (2)C27—O3—H3A109.5
O2—C17—C18122.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O3i0.872.202.907 (3)138
O3—H3A···O20.832.012.805 (3)160
O3—H3A···N10.832.583.170 (3)129
C1—H1···Cl10.942.673.055 (3)106
C10—H10···Cl10.942.653.032 (3)105
C25—H25A···O2ii0.972.583.486 (4)156
Symmetry codes: (i) x+2, y, z; (ii) x+2, y1, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds