3,t-6-Dihydr­oxy-t-5-methoxy­carbonyl-c-6-methyl-r-4-phenyl-4,5,6,7-tetra­hydro-1H-indazole

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.

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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Computing details

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

Crystal data

C16H18N2O4	F(000) = 1280
Mr = 302.32	Dx = 1.342 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9647 reflections
a = 9.3871 (4) Å	θ = 2.7–27.7°
b = 14.7295 (6) Å	µ = 0.10 mm^−1
c = 21.6478 (9) Å	T = 273 K
V = 2993.2 (2) Å^3	Block, colourless
Z = 8	0.19 × 0.11 × 0.09 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2370 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 25.0°, θmin = 1.9°
ω scans	h = −11→11
26831 measured reflections	k = −17→17
2632 independent reflections	l = −25→25

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0535P)^2 + 1.343P] where P = (Fo^2 + 2Fc^2)/3
2632 reflections	(Δ/σ)max < 0.001
207 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.15 e Å^−3

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.

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 (Ų)

	x	y	z	Uiso*/Ueq
O31	0.33404 (12)	−0.06600 (7)	0.02235 (6)	0.0440 (3)
H31	0.4173	−0.0720	0.0116	0.066*
O61	−0.10175 (12)	0.16306 (8)	0.03369 (5)	0.0411 (3)
H61	−0.1707	0.1296	0.0384	0.062*
O52	−0.24705 (14)	0.03714 (9)	0.12300 (6)	0.0532 (3)
N1	0.32774 (15)	0.16630 (9)	0.02600 (7)	0.0408 (4)
H1	0.360 (2)	0.2149 (13)	0.0144 (8)	0.042 (5)*
N2	0.39289 (15)	0.08665 (9)	0.00967 (7)	0.0416 (4)
O51	−0.16175 (18)	0.06279 (12)	0.21727 (7)	0.0743 (5)
C3	0.30506 (17)	0.02246 (10)	0.03013 (7)	0.0350 (4)
C6	−0.03822 (18)	0.18171 (10)	0.09247 (7)	0.0375 (4)
C8	0.20413 (16)	0.15156 (10)	0.05454 (7)	0.0344 (4)
C13	0.09209 (19)	−0.06561 (11)	0.12926 (7)	0.0388 (4)
C4	0.05699 (17)	0.01710 (10)	0.09024 (7)	0.0332 (4)
H4	−0.0109	−0.0011	0.0582	0.040*
C7	0.10587 (17)	0.22332 (10)	0.07691 (8)	0.0396 (4)
H7A	0.0942	0.2694	0.0453	0.048*
H7B	0.1456	0.2521	0.1134	0.048*
C5	−0.01268 (18)	0.09291 (10)	0.13008 (7)	0.0371 (4)
H5	0.0563	0.1081	0.1624	0.045*
C9	0.18474 (16)	0.05924 (10)	0.05933 (7)	0.0325 (4)
C10	−0.1459 (2)	0.06217 (11)	0.16270 (8)	0.0441 (4)
C14	0.1993 (2)	−0.06334 (13)	0.17275 (8)	0.0554 (5)
H14	0.2523	−0.0106	0.1781	0.066*
C18	0.0143 (2)	−0.14464 (12)	0.12230 (10)	0.0561 (5)
H18	−0.0587	−0.1472	0.0933	0.067*
C12	−0.1275 (2)	0.24986 (13)	0.12836 (10)	0.0568 (5)
H12A	−0.1314	0.3061	0.1060	0.085*
H12B	−0.0851	0.2601	0.1681	0.085*
H12C	−0.2221	0.2265	0.1336	0.085*
C15	0.2289 (3)	−0.13924 (16)	0.20871 (9)	0.0742 (7)
H15	0.3013	−0.1371	0.2380	0.089*
C17	0.0444 (3)	−0.21982 (14)	0.15820 (13)	0.0765 (7)
H17	−0.0086	−0.2726	0.1531	0.092*
C16	0.1511 (3)	−0.21734 (15)	0.20099 (11)	0.0783 (8)
H16	0.1710	−0.2683	0.2248	0.094*
C11	−0.3832 (2)	0.01134 (16)	0.14978 (12)	0.0667 (6)
H11A	−0.3702	−0.0402	0.1763	0.100*
H11B	−0.4487	−0.0040	0.1174	0.100*
H11C	−0.4207	0.0612	0.1733	0.100*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O31	0.0356 (6)	0.0256 (6)	0.0708 (8)	−0.0005 (5)	0.0094 (6)	0.0015 (5)
O61	0.0395 (6)	0.0341 (6)	0.0497 (7)	−0.0036 (5)	−0.0043 (5)	0.0085 (5)
O52	0.0424 (7)	0.0634 (8)	0.0539 (8)	−0.0061 (6)	0.0058 (6)	0.0072 (6)
N1	0.0400 (8)	0.0237 (7)	0.0587 (9)	−0.0038 (6)	0.0080 (7)	0.0060 (6)
N2	0.0377 (8)	0.0274 (7)	0.0596 (9)	0.0002 (6)	0.0081 (7)	0.0039 (6)
O51	0.0845 (11)	0.0935 (12)	0.0450 (8)	−0.0235 (9)	0.0187 (8)	0.0017 (7)
C3	0.0351 (8)	0.0259 (8)	0.0439 (9)	−0.0014 (6)	0.0005 (7)	0.0032 (6)
C6	0.0411 (9)	0.0307 (8)	0.0408 (9)	0.0022 (7)	0.0032 (7)	0.0012 (7)
C8	0.0347 (8)	0.0286 (8)	0.0399 (8)	−0.0022 (6)	−0.0016 (7)	0.0031 (6)
C13	0.0478 (9)	0.0299 (8)	0.0386 (9)	0.0022 (7)	0.0093 (7)	0.0032 (6)
C4	0.0360 (8)	0.0292 (8)	0.0344 (8)	−0.0032 (6)	0.0007 (7)	0.0030 (6)
C7	0.0440 (9)	0.0265 (8)	0.0484 (9)	−0.0025 (7)	−0.0008 (8)	−0.0009 (7)
C5	0.0422 (9)	0.0326 (8)	0.0366 (8)	0.0004 (7)	0.0024 (7)	0.0019 (6)
C9	0.0349 (8)	0.0265 (8)	0.0362 (8)	−0.0027 (6)	−0.0016 (6)	0.0029 (6)
C10	0.0527 (10)	0.0348 (9)	0.0449 (10)	0.0015 (8)	0.0082 (8)	0.0038 (7)
C14	0.0790 (14)	0.0422 (10)	0.0450 (10)	0.0092 (10)	−0.0074 (10)	0.0017 (8)
C18	0.0600 (12)	0.0357 (9)	0.0728 (13)	−0.0059 (9)	0.0145 (10)	0.0064 (9)
C12	0.0645 (12)	0.0393 (10)	0.0666 (13)	0.0105 (9)	0.0202 (10)	0.0019 (9)
C15	0.114 (2)	0.0662 (15)	0.0426 (11)	0.0352 (14)	−0.0032 (12)	0.0084 (10)
C17	0.0964 (18)	0.0357 (11)	0.0975 (18)	−0.0013 (11)	0.0368 (16)	0.0186 (11)
C16	0.128 (2)	0.0465 (13)	0.0600 (14)	0.0312 (14)	0.0363 (15)	0.0243 (10)
C11	0.0471 (12)	0.0663 (14)	0.0868 (16)	−0.0071 (10)	0.0125 (11)	0.0084 (12)

Geometric parameters (Å, º)

O31—C3	1.3417 (18)	C4—C5	1.555 (2)
O31—H31	0.8200	C4—H4	0.9800
O61—C6	1.4319 (19)	C7—H7A	0.9700
O61—H61	0.8200	C7—H7B	0.9700
O52—C10	1.333 (2)	C5—C10	1.506 (2)
O52—C11	1.454 (2)	C5—H5	0.9800
N1—C8	1.332 (2)	C14—C15	1.390 (3)
N1—N2	1.3694 (19)	C14—H14	0.9300
N1—H1	0.82 (2)	C18—C17	1.382 (3)
N2—C3	1.330 (2)	C18—H18	0.9300
O51—C10	1.191 (2)	C12—H12A	0.9600
C3—C9	1.403 (2)	C12—H12B	0.9600
C6—C12	1.521 (2)	C12—H12C	0.9600
C6—C7	1.523 (2)	C15—C16	1.373 (4)
C6—C5	1.559 (2)	C15—H15	0.9300
C8—C9	1.376 (2)	C17—C16	1.364 (4)
C8—C7	1.484 (2)	C17—H17	0.9300
C13—C14	1.379 (3)	C16—H16	0.9300
C13—C18	1.382 (2)	C11—H11A	0.9600
C13—C4	1.519 (2)	C11—H11B	0.9600
C4—C9	1.507 (2)	C11—H11C	0.9600
C3—O31—H31	109.5	C10—C5—H5	106.4
C6—O61—H61	109.5	C4—C5—H5	106.4
C10—O52—C11	116.22 (15)	C6—C5—H5	106.4
C8—N1—N2	111.65 (13)	C8—C9—C3	103.95 (13)
C8—N1—H1	127.5 (13)	C8—C9—C4	123.08 (14)
N2—N1—H1	120.4 (13)	C3—C9—C4	132.96 (14)
C3—N2—N1	104.26 (13)	O51—C10—O52	123.55 (18)
N2—C3—O31	121.52 (14)	O51—C10—C5	124.54 (18)
N2—C3—C9	111.98 (14)	O52—C10—C5	111.87 (14)
O31—C3—C9	126.50 (14)	C13—C14—C15	120.6 (2)
O61—C6—C12	110.56 (14)	C13—C14—H14	119.7
O61—C6—C7	104.52 (13)	C15—C14—H14	119.7
C12—C6—C7	109.67 (14)	C17—C18—C13	120.4 (2)
O61—C6—C5	111.54 (12)	C17—C18—H18	119.8
C12—C6—C5	111.81 (13)	C13—C18—H18	119.8
C7—C6—C5	108.45 (13)	C6—C12—H12A	109.5
N1—C8—C9	108.13 (14)	C6—C12—H12B	109.5
N1—C8—C7	125.21 (14)	H12A—C12—H12B	109.5
C9—C8—C7	126.66 (14)	C6—C12—H12C	109.5
C14—C13—C18	118.71 (17)	H12A—C12—H12C	109.5
C14—C13—C4	121.26 (15)	H12B—C12—H12C	109.5
C18—C13—C4	120.03 (16)	C16—C15—C14	120.0 (2)
C9—C4—C13	113.87 (13)	C16—C15—H15	120.0
C9—C4—C5	106.56 (12)	C14—C15—H15	120.0
C13—C4—C5	111.03 (12)	C16—C17—C18	120.7 (2)
C9—C4—H4	108.4	C16—C17—H17	119.7
C13—C4—H4	108.4	C18—C17—H17	119.7
C5—C4—H4	108.4	C17—C16—C15	119.7 (2)
C8—C7—C6	109.73 (13)	C17—C16—H16	120.1
C8—C7—H7A	109.7	C15—C16—H16	120.1
C6—C7—H7A	109.7	O52—C11—H11A	109.5
C8—C7—H7B	109.7	O52—C11—H11B	109.5
C6—C7—H7B	109.7	H11A—C11—H11B	109.5
H7A—C7—H7B	108.2	O52—C11—H11C	109.5
C10—C5—C4	113.17 (13)	H11A—C11—H11C	109.5
C10—C5—C6	111.69 (13)	H11B—C11—H11C	109.5
C4—C5—C6	112.18 (12)
C8—N1—N2—C3	−0.82 (19)	C7—C8—C9—C3	178.70 (15)
N1—N2—C3—O31	179.96 (15)	N1—C8—C9—C4	178.86 (14)
N1—N2—C3—C9	−0.04 (18)	C7—C8—C9—C4	−1.2 (3)
N2—N1—C8—C9	1.36 (19)	N2—C3—C9—C8	0.82 (19)
N2—N1—C8—C7	−178.62 (15)	O31—C3—C9—C8	−179.18 (16)
C14—C13—C4—C9	50.5 (2)	N2—C3—C9—C4	−179.34 (16)
C18—C13—C4—C9	−130.70 (17)	O31—C3—C9—C4	0.7 (3)
C14—C13—C4—C5	−69.8 (2)	C13—C4—C9—C8	−139.80 (15)
C18—C13—C4—C5	109.03 (18)	C5—C4—C9—C8	−17.0 (2)
N1—C8—C7—C6	166.26 (15)	C13—C4—C9—C3	40.4 (2)
C9—C8—C7—C6	−13.7 (2)	C5—C4—C9—C3	163.15 (16)
O61—C6—C7—C8	−73.92 (16)	C11—O52—C10—O51	1.2 (3)
C12—C6—C7—C8	167.53 (14)	C11—O52—C10—C5	−176.48 (15)
C5—C6—C7—C8	45.17 (17)	C4—C5—C10—O51	120.6 (2)
C9—C4—C5—C10	178.14 (13)	C6—C5—C10—O51	−111.7 (2)
C13—C4—C5—C10	−57.34 (18)	C4—C5—C10—O52	−61.81 (18)
C9—C4—C5—C6	50.66 (17)	C6—C5—C10—O52	65.93 (18)
C13—C4—C5—C6	175.18 (13)	C18—C13—C14—C15	0.3 (3)
O61—C6—C5—C10	−81.86 (16)	C4—C13—C14—C15	179.11 (18)
C12—C6—C5—C10	42.5 (2)	C14—C13—C18—C17	−0.3 (3)
C7—C6—C5—C10	163.57 (14)	C4—C13—C18—C17	−179.16 (17)
O61—C6—C5—C4	46.40 (18)	C13—C14—C15—C16	0.1 (3)
C12—C6—C5—C4	170.78 (15)	C13—C18—C17—C16	0.0 (3)
C7—C6—C5—C4	−68.17 (17)	C18—C17—C16—C15	0.3 (4)
N1—C8—C9—C3	−1.28 (18)	C14—C15—C16—C17	−0.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O61^i	0.82 (2)	2.11 (2)	2.9025 (18)	164.3 (18)
O31—H31···N2^ii	0.82	1.85	2.6728 (18)	178
O61—H61···O31^iii	0.82	2.23	2.8758 (16)	136
C7—H7A···O31^iv	0.97	2.57	3.3679 (19)	140
O61—H61···O52	0.82	2.39	3.0065 (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.