11β-Hydroxy­pregna-1,4,16-triene-3,20-dione

The steroidal title compound, C₂₁H₂₆O₃, possesses normal geometrical parameters. Ring A has a 1α-sofa conformation, and rings B and C are in nearly perfect chair conformations. An O—H...O hydrogen bond helps to establish the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.042
• wR factor = 0.109
• Data-to-parameter ratio = 9.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.04 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.77 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C20
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C21
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C21 H26 O3

Alert level G
REFLT03_ALERT_4_G 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.
           From the CIF: _diffrn_reflns_theta_max           25.50
           From the CIF: _reflns_number_total               1959
           Count of symmetry unique reflns         1964
           Completeness (_total/calc)             99.75%
           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

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   3 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
   1 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: RAPID-AUTO (Rigaku, 1999); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

(I)

Crystal data

C21H26O3	Dx = 1.198 Mg m^−3
Mr = 326.42	Melting point: 547 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 12061 reflections
a = 6.2265 (12) Å	θ = 3.4–27.5°
b = 14.862 (3) Å	µ = 0.08 mm^−1
c = 19.561 (4) Å	T = 293 K
V = 1810.1 (6) Å^3	Blade, light yellow
Z = 4	0.37 × 0.13 × 0.04 mm
F(000) = 704

Data collection

Rigaku r-axis rapid IP diffractometer	1959 independent reflections
Radiation source: rotating anode	1544 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.070
ω scans	θmax = 25.5°, θmin = 3.4°
Absorption correction: multi-scan SADABS (Sheldrick, 1996)	h = −7→7
Tmin = 0.972, Tmax = 0.998	k = −18→18
14741 measured reflections	l = −23→23

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.109	w = 1/[σ^2(Fo^2) + (0.0613P)^2 + 0.0192P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.014
1959 reflections	Δρmax = 0.16 e Å^−3
218 parameters	Δρmin = −0.13 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.024 (5)

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
C1	1.0828 (4)	0.74759 (16)	0.20631 (11)	0.0494 (6)
C2	1.2762 (4)	0.77544 (19)	0.24690 (12)	0.0588 (7)
H2A	1.3427	0.7320	0.2738	0.071*
C3	1.3593 (4)	0.8579 (2)	0.24718 (13)	0.0658 (8)
H3A	1.4799	0.8697	0.2738	0.079*
C4	1.2665 (5)	0.9292 (2)	0.20717 (13)	0.0675 (7)
C5	1.0704 (5)	0.90839 (18)	0.17070 (13)	0.0634 (7)
H5A	1.0028	0.9543	0.1466	0.076*
C6	0.9822 (4)	0.82683 (17)	0.17001 (11)	0.0514 (6)
C7	0.7876 (5)	0.80626 (19)	0.12766 (12)	0.0626 (7)
H7A	0.7350	0.8609	0.1064	0.075*
H7B	0.6747	0.7822	0.1565	0.075*
C8	0.8471 (4)	0.73776 (18)	0.07284 (12)	0.0586 (7)
H8A	0.7192	0.7212	0.0474	0.070*
H8B	0.9479	0.7648	0.0411	0.070*
C9	0.9463 (4)	0.65421 (16)	0.10353 (10)	0.0474 (6)
H9A	0.8382	0.6241	0.1318	0.057*
C10	1.1439 (4)	0.67698 (16)	0.14903 (10)	0.0438 (5)
H10A	1.2473	0.7073	0.1191	0.053*
C11	1.2566 (4)	0.59147 (16)	0.17488 (12)	0.0507 (6)
H11A	1.1674	0.5631	0.2101	0.061*
C12	1.3049 (4)	0.52254 (18)	0.11881 (12)	0.0572 (6)
H12A	1.4147	0.5464	0.0887	0.069*
H12B	1.3604	0.4680	0.1395	0.069*
C13	1.1066 (4)	0.49994 (17)	0.07727 (10)	0.0522 (6)
C14	1.0215 (4)	0.58882 (17)	0.04837 (10)	0.0508 (6)
H14A	1.1458	0.6178	0.0270	0.061*
C15	0.8773 (5)	0.5597 (2)	−0.01098 (12)	0.0688 (8)
H15A	0.7344	0.5437	0.0046	0.083*
H15B	0.8671	0.6060	−0.0458	0.083*
C16	0.9975 (6)	0.4796 (2)	−0.03604 (13)	0.0759 (9)
H16A	0.9801	0.4549	−0.0794	0.091*
C17	1.1336 (5)	0.4471 (2)	0.01096 (12)	0.0663 (7)
C18	0.9224 (4)	0.7077 (2)	0.25843 (11)	0.0642 (7)
H18A	0.8894	0.7521	0.2925	0.096*
H18B	0.9852	0.6560	0.2799	0.096*
H18C	0.7931	0.6903	0.2352	0.096*
C19	0.9424 (5)	0.44821 (18)	0.12085 (12)	0.0648 (7)
H19A	1.0067	0.3938	0.1375	0.097*
H19B	0.8194	0.4337	0.0934	0.097*
H19C	0.8988	0.4849	0.1588	0.097*
C20	1.2662 (7)	0.3658 (3)	0.00567 (18)	0.0909 (10)
C21	1.2891 (10)	0.3217 (3)	−0.06385 (19)	0.1337 (18)
H21A	1.3800	0.2697	−0.0600	0.200*
H21B	1.3516	0.3637	−0.0954	0.200*
H21C	1.1502	0.3037	−0.0801	0.200*
O1	1.3469 (4)	1.00530 (16)	0.20423 (11)	0.0970 (8)
O2	1.4570 (3)	0.61767 (12)	0.20450 (11)	0.0763 (6)
H2B	1.4988	0.5781	0.2305	0.115*
O3	1.3481 (6)	0.3327 (2)	0.05579 (15)	0.1334 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0393 (12)	0.0672 (16)	0.0417 (11)	−0.0016 (11)	−0.0014 (10)	−0.0039 (10)
C2	0.0499 (14)	0.0756 (18)	0.0508 (13)	0.0046 (13)	−0.0053 (12)	−0.0087 (12)
C3	0.0489 (13)	0.085 (2)	0.0632 (15)	−0.0056 (15)	0.0022 (13)	−0.0298 (15)
C4	0.0771 (18)	0.0715 (19)	0.0537 (13)	−0.0141 (16)	0.0097 (15)	−0.0210 (13)
C5	0.0732 (17)	0.0603 (16)	0.0566 (13)	0.0080 (14)	0.0005 (14)	−0.0076 (12)
C6	0.0464 (13)	0.0600 (15)	0.0476 (11)	0.0073 (11)	0.0033 (11)	−0.0076 (11)
C7	0.0530 (15)	0.0705 (17)	0.0643 (14)	0.0143 (13)	−0.0071 (13)	−0.0035 (13)
C8	0.0550 (15)	0.0715 (18)	0.0493 (12)	0.0095 (13)	−0.0098 (12)	−0.0005 (12)
C9	0.0413 (12)	0.0629 (15)	0.0378 (10)	0.0007 (11)	−0.0011 (10)	−0.0017 (10)
C10	0.0369 (11)	0.0536 (13)	0.0409 (10)	−0.0019 (9)	0.0004 (10)	0.0030 (10)
C11	0.0464 (12)	0.0539 (14)	0.0518 (12)	−0.0039 (11)	−0.0111 (12)	0.0058 (11)
C12	0.0548 (14)	0.0552 (15)	0.0617 (13)	0.0075 (12)	0.0008 (13)	0.0045 (12)
C13	0.0551 (14)	0.0585 (15)	0.0428 (11)	−0.0024 (12)	0.0044 (11)	−0.0005 (11)
C14	0.0540 (13)	0.0613 (15)	0.0371 (10)	−0.0021 (11)	0.0023 (11)	0.0041 (10)
C15	0.0802 (18)	0.085 (2)	0.0412 (12)	0.0026 (16)	−0.0053 (13)	−0.0061 (13)
C16	0.100 (2)	0.081 (2)	0.0469 (12)	−0.0015 (18)	0.0063 (16)	−0.0137 (14)
C17	0.0800 (18)	0.0664 (18)	0.0523 (13)	−0.0022 (16)	0.0138 (14)	−0.0093 (13)
C18	0.0589 (16)	0.0863 (19)	0.0473 (12)	−0.0060 (15)	0.0090 (13)	−0.0011 (13)
C19	0.0804 (19)	0.0612 (16)	0.0529 (13)	−0.0172 (15)	0.0075 (14)	0.0001 (12)
C20	0.110 (3)	0.076 (2)	0.087 (2)	0.010 (2)	0.015 (2)	−0.0211 (18)
C21	0.177 (5)	0.113 (3)	0.110 (3)	0.024 (3)	0.036 (3)	−0.047 (2)
O1	0.126 (2)	0.0818 (15)	0.0834 (13)	−0.0386 (15)	−0.0014 (15)	−0.0181 (12)
O2	0.0609 (10)	0.0597 (11)	0.1085 (14)	0.0033 (9)	−0.0375 (11)	0.0029 (10)
O3	0.177 (3)	0.103 (2)	0.1204 (19)	0.062 (2)	−0.016 (2)	−0.0230 (17)

Geometric parameters (Å, º)

C1—C2	1.500 (3)	C12—C13	1.516 (3)
C1—C6	1.511 (3)	C12—H12A	0.9700
C1—C18	1.545 (3)	C12—H12B	0.9700
C1—C10	1.582 (3)	C13—C17	1.526 (3)
C2—C3	1.331 (4)	C13—C14	1.531 (3)
C2—H2A	0.9300	C13—C19	1.537 (3)
C3—C4	1.438 (4)	C14—C15	1.530 (3)
C3—H3A	0.9300	C14—H14A	0.9800
C4—O1	1.237 (3)	C15—C16	1.489 (4)
C4—C5	1.448 (4)	C15—H15A	0.9700
C5—C6	1.331 (4)	C15—H15B	0.9700
C5—H5A	0.9300	C16—C17	1.340 (4)
C6—C7	1.499 (4)	C16—H16A	0.9300
C7—C8	1.524 (3)	C17—C20	1.467 (5)
C7—H7A	0.9700	C18—H18A	0.9600
C7—H7B	0.9700	C18—H18B	0.9600
C8—C9	1.511 (4)	C18—H18C	0.9600
C8—H8A	0.9700	C19—H19A	0.9600
C8—H8B	0.9700	C19—H19B	0.9600
C9—C14	1.526 (3)	C19—H19C	0.9600
C9—C10	1.556 (3)	C20—O3	1.209 (4)
C9—H9A	0.9800	C20—C21	1.516 (4)
C10—C11	1.537 (3)	C21—H21A	0.9600
C10—H10A	0.9800	C21—H21B	0.9600
C11—O2	1.430 (3)	C21—H21C	0.9600
C11—C12	1.531 (3)	O2—H2B	0.8200
C11—H11A	0.9800
C2—C1—C6	111.5 (2)	C13—C12—H12A	109.2
C2—C1—C18	105.98 (18)	C11—C12—H12A	109.2
C6—C1—C18	109.9 (2)	C13—C12—H12B	109.2
C2—C1—C10	111.40 (18)	C11—C12—H12B	109.2
C6—C1—C10	106.49 (16)	H12A—C12—H12B	107.9
C18—C1—C10	111.6 (2)	C12—C13—C17	118.7 (2)
C3—C2—C1	124.6 (3)	C12—C13—C14	106.8 (2)
C3—C2—H2A	117.7	C17—C13—C14	99.69 (19)
C1—C2—H2A	117.7	C12—C13—C19	110.81 (18)
C2—C3—C4	121.4 (3)	C17—C13—C19	106.7 (2)
C2—C3—H3A	119.3	C14—C13—C19	114.0 (2)
C4—C3—H3A	119.3	C9—C14—C15	122.5 (2)
O1—C4—C3	122.4 (3)	C9—C14—C13	113.24 (16)
O1—C4—C5	120.9 (3)	C15—C14—C13	103.8 (2)
C3—C4—C5	116.7 (3)	C9—C14—H14A	105.3
C6—C5—C4	123.2 (3)	C15—C14—H14A	105.3
C6—C5—H5A	118.4	C13—C14—H14A	105.3
C4—C5—H5A	118.4	C16—C15—C14	100.4 (2)
C5—C6—C7	121.7 (2)	C16—C15—H15A	111.7
C5—C6—C1	122.3 (2)	C14—C15—H15A	111.7
C7—C6—C1	115.8 (2)	C16—C15—H15B	111.7
C6—C7—C8	109.2 (2)	C14—C15—H15B	111.7
C6—C7—H7A	109.8	H15A—C15—H15B	109.5
C8—C7—H7A	109.8	C17—C16—C15	112.3 (2)
C6—C7—H7B	109.8	C17—C16—H16A	123.8
C8—C7—H7B	109.8	C15—C16—H16A	123.8
H7A—C7—H7B	108.3	C16—C17—C20	127.1 (3)
C9—C8—C7	111.62 (18)	C16—C17—C13	109.2 (2)
C9—C8—H8A	109.3	C20—C17—C13	123.1 (3)
C7—C8—H8A	109.3	C1—C18—H18A	109.5
C9—C8—H8B	109.3	C1—C18—H18B	109.5
C7—C8—H8B	109.3	H18A—C18—H18B	109.5
H8A—C8—H8B	108.0	C1—C18—H18C	109.5
C8—C9—C14	111.59 (17)	H18A—C18—H18C	109.5
C8—C9—C10	111.8 (2)	H18B—C18—H18C	109.5
C14—C9—C10	107.46 (19)	C13—C19—H19A	109.5
C8—C9—H9A	108.6	C13—C19—H19B	109.5
C14—C9—H9A	108.6	H19A—C19—H19B	109.5
C10—C9—H9A	108.6	C13—C19—H19C	109.5
C11—C10—C9	111.68 (18)	H19A—C19—H19C	109.5
C11—C10—C1	115.17 (16)	H19B—C19—H19C	109.5
C9—C10—C1	111.06 (17)	O3—C20—C17	121.0 (3)
C11—C10—H10A	106.1	O3—C20—C21	120.8 (4)
C9—C10—H10A	106.1	C17—C20—C21	118.2 (4)
C1—C10—H10A	106.1	C20—C21—H21A	109.5
O2—C11—C12	107.54 (19)	C20—C21—H21B	109.5
O2—C11—C10	107.85 (18)	H21A—C21—H21B	109.5
C12—C11—C10	114.03 (17)	C20—C21—H21C	109.5
O2—C11—H11A	109.1	H21A—C21—H21C	109.5
C12—C11—H11A	109.1	H21B—C21—H21C	109.5
C10—C11—H11A	109.1	C11—O2—H2B	109.5
C13—C12—C11	111.9 (2)
C6—C1—C2—C3	−4.7 (3)	C9—C10—C11—C12	49.5 (3)
C18—C1—C2—C3	−124.3 (3)	C1—C10—C11—C12	177.43 (19)
C10—C1—C2—C3	114.1 (3)	O2—C11—C12—C13	−171.97 (19)
C1—C2—C3—C4	0.0 (4)	C10—C11—C12—C13	−52.4 (3)
C2—C3—C4—O1	−176.6 (3)	C11—C12—C13—C17	168.1 (2)
C2—C3—C4—C5	4.3 (4)	C11—C12—C13—C14	56.7 (2)
O1—C4—C5—C6	177.3 (3)	C11—C12—C13—C19	−68.0 (3)
C3—C4—C5—C6	−3.6 (4)	C8—C9—C14—C15	−49.8 (3)
C4—C5—C6—C7	−175.6 (2)	C10—C9—C14—C15	−172.8 (2)
C4—C5—C6—C1	−1.4 (4)	C8—C9—C14—C13	−175.4 (2)
C2—C1—C6—C5	5.3 (3)	C10—C9—C14—C13	61.7 (3)
C18—C1—C6—C5	122.5 (3)	C12—C13—C14—C9	−64.1 (3)
C10—C1—C6—C5	−116.4 (2)	C17—C13—C14—C9	171.8 (2)
C2—C1—C6—C7	179.80 (19)	C19—C13—C14—C9	58.6 (3)
C18—C1—C6—C7	−63.0 (2)	C12—C13—C14—C15	160.87 (18)
C10—C1—C6—C7	58.1 (2)	C17—C13—C14—C15	36.8 (2)
C5—C6—C7—C8	115.2 (3)	C19—C13—C14—C15	−76.4 (2)
C1—C6—C7—C8	−59.3 (3)	C9—C14—C15—C16	−164.3 (2)
C6—C7—C8—C9	55.0 (3)	C13—C14—C15—C16	−34.7 (2)
C7—C8—C9—C14	−175.6 (2)	C14—C15—C16—C17	19.4 (3)
C7—C8—C9—C10	−55.2 (3)	C15—C16—C17—C20	175.5 (3)
C8—C9—C10—C11	−174.85 (19)	C15—C16—C17—C13	4.3 (4)
C14—C9—C10—C11	−52.1 (2)	C12—C13—C17—C16	−141.2 (3)
C8—C9—C10—C1	55.1 (2)	C14—C13—C17—C16	−25.9 (3)
C14—C9—C10—C1	177.89 (17)	C19—C13—C17—C16	92.9 (3)
C2—C1—C10—C11	56.3 (3)	C12—C13—C17—C20	47.1 (4)
C6—C1—C10—C11	178.07 (18)	C14—C13—C17—C20	162.4 (3)
C18—C1—C10—C11	−62.0 (3)	C19—C13—C17—C20	−78.8 (4)
C2—C1—C10—C9	−175.5 (2)	C16—C17—C20—O3	−164.4 (4)
C6—C1—C10—C9	−53.7 (2)	C13—C17—C20—O3	5.8 (6)
C18—C1—C10—C9	66.2 (2)	C16—C17—C20—C21	12.7 (6)
C9—C10—C11—O2	168.91 (18)	C13—C17—C20—C21	−177.1 (4)
C1—C10—C11—O2	−63.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···O1^i	0.82	1.93	2.733 (3)	166

Symmetry code: (i) −x+3, y−1/2, −z+1/2.