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In the title compound, C16H18N2O4, the cyclo­hexene ring adopts a half-chair conformation. In the solid state, inter­molecular O—H...N hydrogen bonds link the mol­ecules into dimers. The crystal packing is further stabilized by N—H...O and O—H...O hydrogen bonds and weak C—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806001486/cv6635sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806001486/cv6635Isup2.hkl
Contains datablock I

CCDC reference: 298420

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C)= 0.002 Å
  • R factor = 0.042
  • wR factor = 0.113
  • Data-to-parameter ratio = 12.7

checkCIF/PLATON results

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No errors found in this datablock

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: WinGX (Version 1.64.05; Farrugia, 1999); software used to prepare material for publication: SHELXL97.

3,t-6-Dihydroxy-t-5-methoxycarbonyl-c-6-methyl-r-4-phenyl-4,5,6,7-tetrahydro- 1H-indazole top
Crystal data top
C16H18N2O4F(000) = 1280
Mr = 302.32Dx = 1.342 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 9647 reflections
a = 9.3871 (4) Åθ = 2.7–27.7°
b = 14.7295 (6) ŵ = 0.10 mm1
c = 21.6478 (9) ÅT = 273 K
V = 2993.2 (2) Å3Block, colourless
Z = 80.19 × 0.11 × 0.09 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2370 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
Graphite monochromatorθmax = 25.0°, θmin = 1.9°
ω scansh = 1111
26831 measured reflectionsk = 1717
2632 independent reflectionsl = 2525
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0535P)2 + 1.343P]
where P = (Fo2 + 2Fc2)/3
2632 reflections(Δ/σ)max < 0.001
207 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.15 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
O310.33404 (12)0.06600 (7)0.02235 (6)0.0440 (3)
H310.41730.07200.01160.066*
O610.10175 (12)0.16306 (8)0.03369 (5)0.0411 (3)
H610.17070.12960.03840.062*
O520.24705 (14)0.03714 (9)0.12300 (6)0.0532 (3)
N10.32774 (15)0.16630 (9)0.02600 (7)0.0408 (4)
H10.360 (2)0.2149 (13)0.0144 (8)0.042 (5)*
N20.39289 (15)0.08665 (9)0.00967 (7)0.0416 (4)
O510.16175 (18)0.06279 (12)0.21727 (7)0.0743 (5)
C30.30506 (17)0.02246 (10)0.03013 (7)0.0350 (4)
C60.03822 (18)0.18171 (10)0.09247 (7)0.0375 (4)
C80.20413 (16)0.15156 (10)0.05454 (7)0.0344 (4)
C130.09209 (19)0.06561 (11)0.12926 (7)0.0388 (4)
C40.05699 (17)0.01710 (10)0.09024 (7)0.0332 (4)
H40.01090.00110.05820.040*
C70.10587 (17)0.22332 (10)0.07691 (8)0.0396 (4)
H7A0.09420.26940.04530.048*
H7B0.14560.25210.11340.048*
C50.01268 (18)0.09291 (10)0.13008 (7)0.0371 (4)
H50.05630.10810.16240.045*
C90.18474 (16)0.05924 (10)0.05933 (7)0.0325 (4)
C100.1459 (2)0.06217 (11)0.16270 (8)0.0441 (4)
C140.1993 (2)0.06334 (13)0.17275 (8)0.0554 (5)
H140.25230.01060.17810.066*
C180.0143 (2)0.14464 (12)0.12230 (10)0.0561 (5)
H180.05870.14720.09330.067*
C120.1275 (2)0.24986 (13)0.12836 (10)0.0568 (5)
H12A0.13140.30610.10600.085*
H12B0.08510.26010.16810.085*
H12C0.22210.22650.13360.085*
C150.2289 (3)0.13924 (16)0.20871 (9)0.0742 (7)
H150.30130.13710.23800.089*
C170.0444 (3)0.21982 (14)0.15820 (13)0.0765 (7)
H170.00860.27260.15310.092*
C160.1511 (3)0.21734 (15)0.20099 (11)0.0783 (8)
H160.17100.26830.22480.094*
C110.3832 (2)0.01134 (16)0.14978 (12)0.0667 (6)
H11A0.37020.04020.17630.100*
H11B0.44870.00400.11740.100*
H11C0.42070.06120.17330.100*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O310.0356 (6)0.0256 (6)0.0708 (8)0.0005 (5)0.0094 (6)0.0015 (5)
O610.0395 (6)0.0341 (6)0.0497 (7)0.0036 (5)0.0043 (5)0.0085 (5)
O520.0424 (7)0.0634 (8)0.0539 (8)0.0061 (6)0.0058 (6)0.0072 (6)
N10.0400 (8)0.0237 (7)0.0587 (9)0.0038 (6)0.0080 (7)0.0060 (6)
N20.0377 (8)0.0274 (7)0.0596 (9)0.0002 (6)0.0081 (7)0.0039 (6)
O510.0845 (11)0.0935 (12)0.0450 (8)0.0235 (9)0.0187 (8)0.0017 (7)
C30.0351 (8)0.0259 (8)0.0439 (9)0.0014 (6)0.0005 (7)0.0032 (6)
C60.0411 (9)0.0307 (8)0.0408 (9)0.0022 (7)0.0032 (7)0.0012 (7)
C80.0347 (8)0.0286 (8)0.0399 (8)0.0022 (6)0.0016 (7)0.0031 (6)
C130.0478 (9)0.0299 (8)0.0386 (9)0.0022 (7)0.0093 (7)0.0032 (6)
C40.0360 (8)0.0292 (8)0.0344 (8)0.0032 (6)0.0007 (7)0.0030 (6)
C70.0440 (9)0.0265 (8)0.0484 (9)0.0025 (7)0.0008 (8)0.0009 (7)
C50.0422 (9)0.0326 (8)0.0366 (8)0.0004 (7)0.0024 (7)0.0019 (6)
C90.0349 (8)0.0265 (8)0.0362 (8)0.0027 (6)0.0016 (6)0.0029 (6)
C100.0527 (10)0.0348 (9)0.0449 (10)0.0015 (8)0.0082 (8)0.0038 (7)
C140.0790 (14)0.0422 (10)0.0450 (10)0.0092 (10)0.0074 (10)0.0017 (8)
C180.0600 (12)0.0357 (9)0.0728 (13)0.0059 (9)0.0145 (10)0.0064 (9)
C120.0645 (12)0.0393 (10)0.0666 (13)0.0105 (9)0.0202 (10)0.0019 (9)
C150.114 (2)0.0662 (15)0.0426 (11)0.0352 (14)0.0032 (12)0.0084 (10)
C170.0964 (18)0.0357 (11)0.0975 (18)0.0013 (11)0.0368 (16)0.0186 (11)
C160.128 (2)0.0465 (13)0.0600 (14)0.0312 (14)0.0363 (15)0.0243 (10)
C110.0471 (12)0.0663 (14)0.0868 (16)0.0071 (10)0.0125 (11)0.0084 (12)
Geometric parameters (Å, º) top
O31—C31.3417 (18)C4—C51.555 (2)
O31—H310.8200C4—H40.9800
O61—C61.4319 (19)C7—H7A0.9700
O61—H610.8200C7—H7B0.9700
O52—C101.333 (2)C5—C101.506 (2)
O52—C111.454 (2)C5—H50.9800
N1—C81.332 (2)C14—C151.390 (3)
N1—N21.3694 (19)C14—H140.9300
N1—H10.82 (2)C18—C171.382 (3)
N2—C31.330 (2)C18—H180.9300
O51—C101.191 (2)C12—H12A0.9600
C3—C91.403 (2)C12—H12B0.9600
C6—C121.521 (2)C12—H12C0.9600
C6—C71.523 (2)C15—C161.373 (4)
C6—C51.559 (2)C15—H150.9300
C8—C91.376 (2)C17—C161.364 (4)
C8—C71.484 (2)C17—H170.9300
C13—C141.379 (3)C16—H160.9300
C13—C181.382 (2)C11—H11A0.9600
C13—C41.519 (2)C11—H11B0.9600
C4—C91.507 (2)C11—H11C0.9600
C3—O31—H31109.5C10—C5—H5106.4
C6—O61—H61109.5C4—C5—H5106.4
C10—O52—C11116.22 (15)C6—C5—H5106.4
C8—N1—N2111.65 (13)C8—C9—C3103.95 (13)
C8—N1—H1127.5 (13)C8—C9—C4123.08 (14)
N2—N1—H1120.4 (13)C3—C9—C4132.96 (14)
C3—N2—N1104.26 (13)O51—C10—O52123.55 (18)
N2—C3—O31121.52 (14)O51—C10—C5124.54 (18)
N2—C3—C9111.98 (14)O52—C10—C5111.87 (14)
O31—C3—C9126.50 (14)C13—C14—C15120.6 (2)
O61—C6—C12110.56 (14)C13—C14—H14119.7
O61—C6—C7104.52 (13)C15—C14—H14119.7
C12—C6—C7109.67 (14)C17—C18—C13120.4 (2)
O61—C6—C5111.54 (12)C17—C18—H18119.8
C12—C6—C5111.81 (13)C13—C18—H18119.8
C7—C6—C5108.45 (13)C6—C12—H12A109.5
N1—C8—C9108.13 (14)C6—C12—H12B109.5
N1—C8—C7125.21 (14)H12A—C12—H12B109.5
C9—C8—C7126.66 (14)C6—C12—H12C109.5
C14—C13—C18118.71 (17)H12A—C12—H12C109.5
C14—C13—C4121.26 (15)H12B—C12—H12C109.5
C18—C13—C4120.03 (16)C16—C15—C14120.0 (2)
C9—C4—C13113.87 (13)C16—C15—H15120.0
C9—C4—C5106.56 (12)C14—C15—H15120.0
C13—C4—C5111.03 (12)C16—C17—C18120.7 (2)
C9—C4—H4108.4C16—C17—H17119.7
C13—C4—H4108.4C18—C17—H17119.7
C5—C4—H4108.4C17—C16—C15119.7 (2)
C8—C7—C6109.73 (13)C17—C16—H16120.1
C8—C7—H7A109.7C15—C16—H16120.1
C6—C7—H7A109.7O52—C11—H11A109.5
C8—C7—H7B109.7O52—C11—H11B109.5
C6—C7—H7B109.7H11A—C11—H11B109.5
H7A—C7—H7B108.2O52—C11—H11C109.5
C10—C5—C4113.17 (13)H11A—C11—H11C109.5
C10—C5—C6111.69 (13)H11B—C11—H11C109.5
C4—C5—C6112.18 (12)
C8—N1—N2—C30.82 (19)C7—C8—C9—C3178.70 (15)
N1—N2—C3—O31179.96 (15)N1—C8—C9—C4178.86 (14)
N1—N2—C3—C90.04 (18)C7—C8—C9—C41.2 (3)
N2—N1—C8—C91.36 (19)N2—C3—C9—C80.82 (19)
N2—N1—C8—C7178.62 (15)O31—C3—C9—C8179.18 (16)
C14—C13—C4—C950.5 (2)N2—C3—C9—C4179.34 (16)
C18—C13—C4—C9130.70 (17)O31—C3—C9—C40.7 (3)
C14—C13—C4—C569.8 (2)C13—C4—C9—C8139.80 (15)
C18—C13—C4—C5109.03 (18)C5—C4—C9—C817.0 (2)
N1—C8—C7—C6166.26 (15)C13—C4—C9—C340.4 (2)
C9—C8—C7—C613.7 (2)C5—C4—C9—C3163.15 (16)
O61—C6—C7—C873.92 (16)C11—O52—C10—O511.2 (3)
C12—C6—C7—C8167.53 (14)C11—O52—C10—C5176.48 (15)
C5—C6—C7—C845.17 (17)C4—C5—C10—O51120.6 (2)
C9—C4—C5—C10178.14 (13)C6—C5—C10—O51111.7 (2)
C13—C4—C5—C1057.34 (18)C4—C5—C10—O5261.81 (18)
C9—C4—C5—C650.66 (17)C6—C5—C10—O5265.93 (18)
C13—C4—C5—C6175.18 (13)C18—C13—C14—C150.3 (3)
O61—C6—C5—C1081.86 (16)C4—C13—C14—C15179.11 (18)
C12—C6—C5—C1042.5 (2)C14—C13—C18—C170.3 (3)
C7—C6—C5—C10163.57 (14)C4—C13—C18—C17179.16 (17)
O61—C6—C5—C446.40 (18)C13—C14—C15—C160.1 (3)
C12—C6—C5—C4170.78 (15)C13—C18—C17—C160.0 (3)
C7—C6—C5—C468.17 (17)C18—C17—C16—C150.3 (4)
N1—C8—C9—C31.28 (18)C14—C15—C16—C170.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O61i0.82 (2)2.11 (2)2.9025 (18)164.3 (18)
O31—H31···N2ii0.821.852.6728 (18)178
O61—H61···O31iii0.822.232.8758 (16)136
C7—H7A···O31iv0.972.573.3679 (19)140
O61—H61···O520.822.393.0065 (16)132
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x+1, y, z; (iii) x, y, z; (iv) x+1/2, y+1/2, z.
 

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