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The regio- and stereochemistry of the title compound, C26H30N2O, has been established by X-ray analysis. The configuration of the stereogenic centre at C-16 proved to be S and the H atom at C-16 adopts the β position.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680201125X/ya6104sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680201125X/ya6104Isup2.hkl
Contains datablock I

CCDC reference: 193730

Key indicators

  • Single-crystal X-ray study
  • T = 133 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.038
  • wR factor = 0.092
  • Data-to-parameter ratio = 7.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Amber Alert Alert Level B:
ABSMU_01 Alert B The ratio of given/expected absorption coefficient lies outside the range 0.95 <> 1.05 Calculated value of mu = 0.076 Value of mu given = 0.080
Yellow Alert Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 24.70 From the CIF: _reflns_number_total 1939 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 2079 Completeness (_total/calc) 93.27% Alert C: < 95% complete REFNR_01 Alert C Ratio of reflections to parameters is < 8 for a non-centrosymmetric structure, where ZMAX < 18 sine(theta)/lambda 0.5879 Proportion of unique data used 1.0000 Ratio reflections to parameters 7.3447 STRVAL_01 From the CIF: _refine_ls_abs_structure_Flack -1.000 From the CIF: _refine_ls_abs_structure_Flack_su 3.000 Alert C Flack parameter is too small THETM_01 Alert C The value of sine(theta_max)/wavelength is less than 0.590 Calculated sin(theta_max)/wavelength = 0.5879 General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 24.70 From the CIF: _reflns_number_total 1939 Count of symmetry unique reflns 2079 Completeness (_total/calc) 93.27% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
4 Alert Level C = Please check

Computing details top

Data collection: SMART (Siemens 1996); cell refinement: SAINT (Bruker 1997b); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

3-methoxy-1'-phenyl-4'β,5-dihydro-1H-pyrazolo [4',3':16,17]estra-1,3,5(10)-triene top
Crystal data top
C26H30N2ODx = 1.246 Mg m3
Mr = 386.52Melting point = 451–453 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
a = 6.120 (1) ÅCell parameters from 3250 reflections
b = 8.950 (1) Åθ = 2.2–24.7°
c = 37.622 (4) ŵ = 0.08 mm1
V = 2060.7 (5) Å3T = 133 K
Z = 4Block, colourless
F(000) = 8320.3 × 0.2 × 0.2 mm
Data collection top
Locally modified Stoe-Siemens-Huber four-circles
diffractometer
1939 independent reflections
Radiation source: fine-focus sealed tube1669 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
Detector resolution: 0 pixels mm-1θmax = 24.7°, θmin = 2.2°
φ and ω scansh = 66
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)
k = 010
Tmin = 0.978, Tmax = 0.985l = 043
23229 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.092 w = 1/[σ2(Fo2) + (0.0444P)2 + 0.5351P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
1939 reflectionsΔρmax = 0.13 e Å3
264 parametersΔρmin = 0.16 e Å3
0 restraintsAbsolute structure: Flack (1983); Friedel pairs were merged due to the lack of anomalous scatterers
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 1 (3)
Special details top

Experimental. intnesities were measured with a SIEMENS CCD area-detector

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. The hydrogen atoms were included in calculated positions and refined using a riding model.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O0.0061 (4)0.5755 (2)0.06171 (4)0.0400 (5)
N10.1372 (4)0.1795 (2)0.23953 (5)0.0379 (6)
C10.2376 (5)0.3910 (3)0.01525 (7)0.0359 (7)
H10.35480.32420.01990.043*
C1'0.2936 (5)0.1872 (3)0.26636 (7)0.0348 (7)
N20.2147 (4)0.1367 (2)0.20503 (6)0.0372 (6)
C20.2025 (5)0.4380 (3)0.01926 (7)0.0384 (7)
H20.29490.40380.03780.046*
C2'0.4724 (5)0.0914 (3)0.26608 (7)0.0389 (7)
H2'0.49210.02390.24690.047*
C30.0318 (5)0.5355 (3)0.02674 (7)0.0349 (7)
C3'0.6211 (6)0.0938 (4)0.29356 (7)0.0476 (8)
H3'0.74160.02690.29330.057*
C40.1009 (5)0.5840 (3)0.00060 (7)0.0385 (7)
H40.21860.65000.00430.046*
C4'0.5972 (5)0.1927 (4)0.32168 (7)0.0465 (8)
H4'0.70190.19530.34030.056*
C50.0633 (5)0.5362 (3)0.03582 (7)0.0364 (7)
C5'0.4206 (6)0.2867 (3)0.32223 (8)0.0458 (8)
H5'0.40250.35390.34150.055*
C60.2191 (6)0.5950 (3)0.06378 (7)0.0460 (8)
H6A0.23370.70450.06090.055*
H6B0.36490.55000.05990.055*
C6'0.2672 (6)0.2850 (3)0.29488 (7)0.0403 (7)
H6'0.14500.35040.29570.048*
C70.1462 (6)0.5618 (3)0.10172 (7)0.0416 (8)
H7A0.27070.57540.11820.050*
H7B0.02900.63210.10870.050*
C80.0625 (5)0.4022 (3)0.10416 (7)0.0329 (7)
H80.17570.33410.09390.039*
C90.1472 (5)0.3875 (3)0.08187 (7)0.0309 (7)
H90.25550.45890.09230.037*
C100.1070 (5)0.4381 (3)0.04355 (7)0.0317 (7)
C110.2501 (5)0.2307 (3)0.08453 (6)0.0329 (7)
H11A0.15770.15900.07130.039*
H11B0.39560.23250.07300.039*
C120.2763 (5)0.1752 (3)0.12311 (6)0.0338 (7)
H12A0.38880.23590.13530.041*
H12B0.32640.07000.12290.041*
C130.0623 (5)0.1861 (3)0.14338 (7)0.0331 (7)
C140.0145 (5)0.3523 (3)0.14183 (7)0.0314 (7)
H140.11310.41330.14990.038*
C150.1902 (5)0.3701 (3)0.17088 (7)0.0355 (7)
H15A0.18570.47160.18130.043*
H15B0.33800.35200.16110.043*
C160.1316 (5)0.2510 (3)0.19906 (7)0.0389 (7)
H160.25520.17900.20200.047*
C16A0.0369 (5)0.2924 (3)0.23511 (7)0.0371 (7)
H16A0.14820.28430.25410.044*
H16B0.02370.39500.23500.044*
C170.0650 (5)0.1723 (3)0.18332 (7)0.0355 (7)
C180.1070 (5)0.0766 (3)0.12888 (7)0.0427 (8)
H18A0.05660.02600.13290.064*
H18B0.24650.09190.14110.064*
H18C0.12640.09350.10330.064*
C190.1755 (6)0.6699 (3)0.06984 (8)0.0459 (9)
H19A0.31160.61940.06320.069*
H19B0.16260.76360.05650.069*
H19C0.17690.69160.09540.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O0.0492 (14)0.0333 (10)0.0376 (10)0.0016 (11)0.0036 (10)0.0042 (9)
N10.0433 (16)0.0369 (12)0.0335 (12)0.0074 (13)0.0108 (12)0.0024 (10)
C10.0304 (17)0.0346 (14)0.0428 (15)0.0052 (15)0.0014 (14)0.0016 (12)
C1'0.041 (2)0.0317 (14)0.0319 (14)0.0019 (15)0.0124 (14)0.0100 (12)
N20.0441 (17)0.0315 (12)0.0362 (12)0.0047 (12)0.0096 (13)0.0021 (10)
C20.037 (2)0.0389 (15)0.0393 (15)0.0008 (16)0.0040 (14)0.0018 (13)
C2'0.0415 (19)0.0409 (15)0.0344 (14)0.0075 (16)0.0149 (15)0.0057 (13)
C30.0400 (19)0.0283 (13)0.0363 (15)0.0091 (15)0.0020 (14)0.0008 (12)
C3'0.041 (2)0.0625 (19)0.0390 (16)0.0132 (18)0.0128 (16)0.0093 (15)
C40.0400 (19)0.0277 (13)0.0480 (16)0.0063 (15)0.0068 (15)0.0027 (12)
C4'0.039 (2)0.063 (2)0.0374 (15)0.0033 (19)0.0044 (15)0.0028 (16)
C50.038 (2)0.0294 (13)0.0415 (15)0.0034 (15)0.0015 (14)0.0035 (12)
C5'0.055 (2)0.0425 (16)0.0394 (16)0.0010 (18)0.0033 (17)0.0047 (13)
C60.046 (2)0.0447 (17)0.0479 (16)0.0188 (17)0.0091 (16)0.0040 (14)
C6'0.044 (2)0.0323 (14)0.0443 (16)0.0052 (15)0.0094 (16)0.0026 (12)
C70.044 (2)0.0359 (15)0.0445 (16)0.0121 (16)0.0059 (15)0.0031 (13)
C80.0294 (18)0.0331 (14)0.0360 (14)0.0008 (14)0.0022 (13)0.0058 (12)
C90.0232 (16)0.0305 (14)0.0391 (14)0.0025 (13)0.0015 (13)0.0039 (12)
C100.0288 (17)0.0267 (13)0.0397 (14)0.0007 (14)0.0001 (14)0.0026 (11)
C110.0273 (17)0.0359 (14)0.0356 (13)0.0056 (14)0.0001 (14)0.0040 (12)
C120.0278 (18)0.0339 (14)0.0396 (14)0.0059 (14)0.0032 (13)0.0019 (12)
C130.0306 (19)0.0303 (13)0.0385 (15)0.0017 (14)0.0025 (13)0.0033 (12)
C140.0270 (18)0.0275 (13)0.0396 (14)0.0004 (14)0.0010 (13)0.0052 (12)
C150.0288 (18)0.0356 (15)0.0420 (15)0.0003 (13)0.0046 (14)0.0040 (12)
C160.0330 (18)0.0372 (15)0.0467 (16)0.0013 (15)0.0125 (15)0.0017 (13)
C16A0.0358 (18)0.0348 (14)0.0406 (15)0.0051 (14)0.0119 (14)0.0040 (13)
C170.039 (2)0.0270 (13)0.0400 (15)0.0007 (15)0.0034 (15)0.0006 (12)
C180.043 (2)0.0350 (14)0.0504 (17)0.0031 (16)0.0023 (16)0.0049 (13)
C190.056 (2)0.0346 (15)0.0471 (16)0.0048 (17)0.0088 (16)0.0064 (13)
Geometric parameters (Å, º) top
O—C31.373 (3)C5—C61.514 (4)
O—C191.430 (4)C5'—C6'1.393 (4)
N1—C1'1.393 (3)C6—C71.525 (4)
N1—N21.434 (3)C7—C81.521 (4)
N1—C16A1.478 (3)C8—C141.514 (4)
C1—C21.382 (4)C8—C91.539 (4)
C1—C101.397 (4)C9—C101.531 (4)
C1'—C2'1.390 (4)C9—C111.542 (4)
C1'—C6'1.395 (4)C11—C121.543 (3)
N2—C171.268 (4)C12—C131.519 (4)
C2—C31.390 (4)C13—C171.508 (4)
C2'—C3'1.378 (4)C13—C181.527 (4)
C3—C41.381 (4)C13—C141.562 (4)
C3'—C4'1.387 (4)C14—C151.542 (4)
C4—C51.411 (4)C15—C161.546 (4)
C4'—C5'1.369 (4)C16—C171.514 (4)
C5—C101.393 (4)C16—C16A1.521 (4)
C3—O—C19116.7 (2)C7—C8—C9109.2 (2)
C1'—N1—N2116.2 (2)C10—C9—C8110.7 (2)
C1'—N1—C16A122.9 (2)C10—C9—C11113.3 (2)
N2—N1—C16A108.6 (2)C8—C9—C11112.5 (2)
C2—C1—C10122.4 (3)C5—C10—C1117.3 (2)
C2'—C1'—N1120.3 (2)C5—C10—C9120.2 (2)
C2'—C1'—C6'119.0 (3)C1—C10—C9122.5 (2)
N1—C1'—C6'120.6 (3)C9—C11—C12113.4 (2)
C17—N2—N1106.1 (2)C13—C12—C11111.2 (2)
C1—C2—C3119.9 (3)C17—C13—C12119.1 (2)
C3'—C2'—C1'120.3 (3)C17—C13—C18108.1 (2)
O—C3—C4124.4 (3)C12—C13—C18111.4 (2)
O—C3—C2116.4 (2)C17—C13—C1496.8 (2)
C4—C3—C2119.3 (2)C12—C13—C14107.6 (2)
C2'—C3'—C4'120.9 (3)C18—C13—C14113.2 (2)
C3—C4—C5120.5 (3)C8—C14—C15119.8 (2)
C5'—C4'—C3'119.1 (3)C8—C14—C13112.0 (2)
C10—C5—C4120.6 (3)C15—C14—C13106.4 (2)
C10—C5—C6123.0 (2)C14—C15—C16104.7 (2)
C4—C5—C6116.4 (3)C17—C16—C16A99.2 (2)
C4'—C5'—C6'120.9 (3)C17—C16—C15103.7 (2)
C5—C6—C7113.5 (3)C16A—C16—C15122.2 (2)
C5'—C6'—C1'119.8 (3)N1—C16A—C16102.0 (2)
C8—C7—C6109.8 (2)N2—C17—C13132.1 (3)
C14—C8—C7113.5 (2)N2—C17—C16116.1 (2)
C14—C8—C9108.8 (2)C13—C17—C16110.1 (2)
 

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