(E)-16-(4-Chloro-benzyl-idene)estrone.

In the title compound, C25H25ClO2, the C ring adopts a chair conformation, while the B ring approximates a half-chair conformation. The five-membered ring D has a twist con-form-ation on the C-C bond fused with the C ring. Aromatic rings A and E are not coplanar, as evidenced by the dihedral angle of 7.51 (1)°. In the crystal, O-H⋯O hydrogen bonds form a double chain along the ab plane inter-connected by C-H⋯O inter-actions.

Related literature

For applications of steroids as radiodiagnostic compounds and drug delivery systems, see: Katzenellenbogen (1995 ▶); Silva et al. (2001 ▶); Wang et al. (2003 ▶). For related compounds, see: Cooper et al. (1969 ▶); Cody et al. (1971 ▶); Rajnikant et al. (2006 ▶); Gunasekaran et al. (2009 ▶). For conformational analysis of ring systems, see: Cremer & Pople (1975 ▶); Duax et al. (1976 ▶).

Experimental

Crystal data

C25H25ClO2

M = 392.90

Orthorhombic,

a = 6.3601 (3) Å

b = 11.2012 (6) Å

c = 28.3043 (14) Å

V = 2016.42 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 293 K

0.17 × 0.15 × 0.13 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.967, T max = 0.974

23011 measured reflections

4819 independent reflections

3788 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.100

S = 1.02

4819 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.26 e Å−3

Absolute structure: Flack (1983 ▶), 2037 Friedel pairs

Flack parameter: 0.06 (7)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812050349/bh2467sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812050349/bh2467Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C25H25ClO2	Dx = 1.294 Mg m−3
Mr = 392.90	Melting point: 458 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2000 reflections
a = 6.3601 (3) Å	θ = 2–31°
b = 11.2012 (6) Å	µ = 0.21 mm−1
c = 28.3043 (14) Å	T = 293 K
V = 2016.42 (18) Å3	Block, colourless
Z = 4	0.17 × 0.15 × 0.13 mm
F(000) = 832

Bruker Kappa APEXII diffractometer	4819 independent reflections
Radiation source: fine-focus sealed tube	3788 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 0 pixels mm-1	θmax = 27.9°, θmin = 2.3°
ω and φ scans	h = −8→7
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −14→14
Tmin = 0.967, Tmax = 0.974	l = −37→36
23011 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H-atom parameters constrained
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.0435P)2 + 0.2966P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
4819 reflections	Δρmax = 0.22 e Å−3
253 parameters	Δρmin = −0.26 e Å−3
0 restraints	Absolute structure: Flack (1983), 2037 Friedel pairs
0 constraints	Flack parameter: 0.06 (7)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
C1	0.2517 (3)	−0.05590 (16)	0.09206 (6)	0.0420 (4)
H1A	0.1200	−0.0754	0.1041	0.050*
C2	0.3552 (3)	−0.13702 (16)	0.06397 (7)	0.0448 (4)
C3	0.5521 (3)	−0.10893 (17)	0.04649 (7)	0.0478 (5)
H3	0.6251	−0.1634	0.0279	0.057*
C4	0.6387 (3)	0.00039 (17)	0.05695 (7)	0.0451 (4)
H4	0.7713	0.0184	0.0451	0.054*
C5	0.5365 (3)	0.08533 (15)	0.08452 (6)	0.0369 (4)
C6	0.3391 (3)	0.05456 (16)	0.10293 (6)	0.0367 (4)
C7	0.2169 (3)	0.13852 (16)	0.13436 (7)	0.0452 (5)
H7A	0.1693	0.0949	0.1620	0.054*
H7B	0.0932	0.1657	0.1174	0.054*
C8	0.3413 (3)	0.24637 (17)	0.15048 (7)	0.0456 (5)
H8A	0.4355	0.2234	0.1759	0.055*
H8B	0.2459	0.3067	0.1625	0.055*
C9	0.4680 (3)	0.29775 (15)	0.10975 (6)	0.0358 (4)
H9	0.3731	0.3114	0.0830	0.043*
C10	0.6358 (3)	0.20596 (16)	0.09476 (6)	0.0367 (4)
H10	0.7275	0.1944	0.1222	0.044*
C11	0.7758 (3)	0.25270 (16)	0.05509 (7)	0.0461 (5)
H11A	0.6930	0.2589	0.0264	0.055*
H11B	0.8873	0.1954	0.0493	0.055*
C12	0.8747 (3)	0.37515 (17)	0.06580 (7)	0.0486 (5)
H12A	0.9754	0.3673	0.0914	0.058*
H12B	0.9489	0.4040	0.0381	0.058*
C13	0.7053 (3)	0.46360 (16)	0.07958 (6)	0.0394 (4)
C14A	0.5673 (3)	0.49699 (18)	0.03654 (7)	0.0533 (5)
H14A	0.4614	0.5531	0.0461	0.080*
H14B	0.5012	0.4264	0.0243	0.080*
H14C	0.6537	0.5322	0.0125	0.080*
C15	0.5779 (3)	0.41378 (15)	0.12129 (6)	0.0362 (4)
H15	0.6805	0.3949	0.1460	0.043*
C16	0.4532 (3)	0.52206 (15)	0.13940 (7)	0.0420 (4)
H16A	0.3278	0.5355	0.1206	0.050*
H16B	0.4135	0.5122	0.1723	0.050*
C17	0.6101 (3)	0.62256 (17)	0.13336 (7)	0.0433 (4)
C18	0.7770 (3)	0.58149 (17)	0.10050 (7)	0.0449 (4)
C19	0.6214 (3)	0.73160 (17)	0.15245 (7)	0.0464 (5)
H19	0.7401	0.7754	0.1442	0.056*
C20	0.4751 (3)	0.79255 (16)	0.18433 (7)	0.0459 (4)
C21	0.2732 (4)	0.75169 (18)	0.19375 (8)	0.0574 (6)
H21	0.2274	0.6811	0.1798	0.069*
C22	0.1395 (4)	0.8131 (2)	0.22317 (8)	0.0610 (6)
H22	0.0065	0.7831	0.2299	0.073*
C23	0.2042 (4)	0.91873 (19)	0.24246 (7)	0.0544 (5)
C24	0.4006 (4)	0.9632 (2)	0.23352 (8)	0.0598 (6)
H24	0.4434	1.0350	0.2469	0.072*
C25	0.5342 (4)	0.90013 (18)	0.20449 (7)	0.0538 (5)
H25	0.6674	0.9305	0.1983	0.065*
O1	0.2750 (2)	−0.24606 (12)	0.05227 (6)	0.0622 (4)
H1	0.1584	−0.2538	0.0642	0.093*
O2	0.9391 (2)	0.63375 (13)	0.09181 (6)	0.0698 (5)
Cl1	0.03190 (11)	0.99936 (6)	0.27780 (3)	0.0845 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0336 (9)	0.0398 (10)	0.0525 (11)	−0.0008 (8)	0.0016 (8)	0.0097 (9)
C2	0.0501 (11)	0.0320 (10)	0.0524 (11)	−0.0018 (8)	−0.0056 (9)	0.0039 (8)
C3	0.0495 (11)	0.0361 (10)	0.0577 (11)	0.0013 (9)	0.0092 (10)	−0.0032 (9)
C4	0.0377 (9)	0.0409 (11)	0.0568 (11)	0.0017 (8)	0.0105 (9)	−0.0006 (9)
C5	0.0341 (8)	0.0333 (9)	0.0431 (9)	0.0020 (8)	0.0006 (7)	0.0032 (7)
C6	0.0339 (8)	0.0325 (9)	0.0438 (9)	0.0038 (7)	0.0002 (7)	0.0062 (8)
C7	0.0378 (9)	0.0400 (10)	0.0580 (11)	−0.0005 (8)	0.0134 (9)	0.0061 (9)
C8	0.0465 (10)	0.0391 (11)	0.0512 (11)	0.0010 (9)	0.0156 (9)	−0.0010 (9)
C9	0.0342 (8)	0.0346 (9)	0.0386 (9)	0.0004 (7)	0.0058 (7)	0.0005 (7)
C10	0.0312 (8)	0.0350 (9)	0.0439 (10)	0.0017 (7)	0.0010 (8)	0.0002 (8)
C11	0.0417 (10)	0.0403 (10)	0.0564 (11)	−0.0024 (9)	0.0148 (9)	−0.0033 (9)
C12	0.0417 (10)	0.0448 (11)	0.0592 (12)	−0.0069 (9)	0.0138 (9)	−0.0033 (9)
C13	0.0384 (9)	0.0354 (10)	0.0445 (10)	−0.0052 (8)	0.0049 (8)	0.0023 (8)
C14A	0.0700 (13)	0.0475 (12)	0.0425 (10)	−0.0061 (11)	−0.0005 (9)	0.0057 (9)
C15	0.0350 (8)	0.0336 (9)	0.0399 (9)	−0.0022 (7)	0.0014 (7)	0.0010 (7)
C16	0.0439 (9)	0.0369 (10)	0.0452 (10)	−0.0026 (8)	0.0046 (8)	−0.0027 (8)
C17	0.0461 (10)	0.0369 (10)	0.0469 (10)	−0.0015 (8)	−0.0024 (8)	0.0003 (8)
C18	0.0425 (10)	0.0384 (10)	0.0538 (11)	−0.0061 (9)	0.0019 (9)	0.0023 (9)
C19	0.0480 (11)	0.0397 (11)	0.0515 (11)	−0.0076 (9)	−0.0042 (9)	0.0014 (9)
C20	0.0550 (12)	0.0349 (10)	0.0478 (10)	0.0000 (9)	−0.0085 (9)	−0.0002 (8)
C21	0.0620 (13)	0.0367 (11)	0.0733 (14)	−0.0061 (10)	0.0060 (11)	−0.0110 (10)
C22	0.0599 (13)	0.0450 (12)	0.0783 (15)	0.0008 (10)	0.0035 (12)	−0.0082 (11)
C23	0.0647 (13)	0.0475 (12)	0.0509 (12)	0.0134 (11)	−0.0067 (10)	−0.0081 (10)
C24	0.0730 (15)	0.0440 (12)	0.0625 (13)	0.0030 (11)	−0.0198 (11)	−0.0163 (10)
C25	0.0563 (12)	0.0451 (11)	0.0601 (12)	−0.0018 (10)	−0.0122 (10)	−0.0041 (10)
O1	0.0611 (9)	0.0404 (8)	0.0852 (10)	−0.0128 (7)	0.0066 (8)	−0.0107 (7)
O2	0.0550 (9)	0.0561 (9)	0.0982 (12)	−0.0228 (8)	0.0191 (9)	−0.0089 (9)
Cl1	0.0868 (4)	0.0770 (5)	0.0897 (4)	0.0234 (4)	−0.0009 (4)	−0.0325 (3)

C1—C2	1.375 (3)	C13—C18	1.517 (3)
C1—C6	1.391 (3)	C13—C15	1.537 (2)
C1—H1A	0.9300	C13—C14A	1.547 (3)
C2—O1	1.364 (2)	C14A—H14A	0.9600
C2—C3	1.382 (3)	C14A—H14B	0.9600
C3—C4	1.375 (3)	C14A—H14C	0.9600
C3—H3	0.9300	C15—C16	1.537 (2)
C4—C5	1.391 (2)	C15—H15	0.9800
C4—H4	0.9300	C16—C17	1.514 (3)
C5—C6	1.403 (2)	C16—H16A	0.9700
C5—C10	1.519 (3)	C16—H16B	0.9700
C6—C7	1.510 (3)	C17—C19	1.337 (3)
C7—C8	1.515 (3)	C17—C18	1.484 (3)
C7—H7A	0.9700	C18—O2	1.211 (2)
C7—H7B	0.9700	C19—C20	1.465 (3)
C8—C9	1.520 (2)	C19—H19	0.9300
C8—H8A	0.9700	C20—C25	1.385 (3)
C8—H8B	0.9700	C20—C21	1.389 (3)
C9—C15	1.511 (2)	C21—C22	1.375 (3)
C9—C10	1.542 (2)	C21—H21	0.9300
C9—H9	0.9800	C22—C23	1.367 (3)
C10—C11	1.526 (2)	C22—H22	0.9300
C10—H10	0.9800	C23—C24	1.368 (3)
C11—C12	1.539 (3)	C23—Cl1	1.737 (2)
C11—H11A	0.9700	C24—C25	1.376 (3)
C11—H11B	0.9700	C24—H24	0.9300
C12—C13	1.515 (3)	C25—H25	0.9300
C12—H12A	0.9700	O1—H1	0.8200
C12—H12B	0.9700
C2—C1—C6	121.61 (16)	H12A—C12—H12B	108.2
C2—C1—H1A	119.2	C12—C13—C18	117.13 (15)
C6—C1—H1A	119.2	C12—C13—C15	109.59 (14)
O1—C2—C1	123.56 (18)	C18—C13—C15	100.06 (14)
O1—C2—C3	117.09 (18)	C12—C13—C14A	111.03 (16)
C1—C2—C3	119.35 (17)	C18—C13—C14A	105.50 (15)
C4—C3—C2	119.25 (18)	C15—C13—C14A	113.17 (15)
C4—C3—H3	120.4	C13—C14A—H14A	109.5
C2—C3—H3	120.4	C13—C14A—H14B	109.5
C3—C4—C5	122.86 (17)	H14A—C14A—H14B	109.5
C3—C4—H4	118.6	C13—C14A—H14C	109.5
C5—C4—H4	118.6	H14A—C14A—H14C	109.5
C4—C5—C6	117.27 (16)	H14B—C14A—H14C	109.5
C4—C5—C10	121.40 (16)	C9—C15—C13	112.96 (14)
C6—C5—C10	121.32 (16)	C9—C15—C16	120.79 (14)
C1—C6—C5	119.63 (16)	C13—C15—C16	103.99 (13)
C1—C6—C7	118.60 (16)	C9—C15—H15	106.0
C5—C6—C7	121.77 (16)	C13—C15—H15	106.0
C6—C7—C8	113.92 (15)	C16—C15—H15	106.0
C6—C7—H7A	108.8	C17—C16—C15	102.05 (14)
C8—C7—H7A	108.8	C17—C16—H16A	111.4
C6—C7—H7B	108.8	C15—C16—H16A	111.4
C8—C7—H7B	108.8	C17—C16—H16B	111.4
H7A—C7—H7B	107.7	C15—C16—H16B	111.4
C7—C8—C9	110.52 (15)	H16A—C16—H16B	109.2
C7—C8—H8A	109.5	C19—C17—C18	119.86 (18)
C9—C8—H8A	109.5	C19—C17—C16	131.97 (18)
C7—C8—H8B	109.5	C18—C17—C16	108.15 (15)
C9—C8—H8B	109.5	O2—C18—C17	125.89 (18)
H8A—C8—H8B	108.1	O2—C18—C13	126.68 (18)
C15—C9—C8	114.01 (14)	C17—C18—C13	107.43 (15)
C15—C9—C10	108.23 (14)	C17—C19—C20	129.83 (18)
C8—C9—C10	108.86 (14)	C17—C19—H19	115.1
C15—C9—H9	108.5	C20—C19—H19	115.1
C8—C9—H9	108.5	C25—C20—C21	117.27 (19)
C10—C9—H9	108.5	C25—C20—C19	119.16 (19)
C5—C10—C11	114.03 (15)	C21—C20—C19	123.48 (17)
C5—C10—C9	110.97 (14)	C22—C21—C20	121.56 (19)
C11—C10—C9	112.19 (14)	C22—C21—H21	119.2
C5—C10—H10	106.4	C20—C21—H21	119.2
C11—C10—H10	106.4	C23—C22—C21	119.3 (2)
C9—C10—H10	106.4	C23—C22—H22	120.4
C10—C11—C12	113.53 (15)	C21—C22—H22	120.4
C10—C11—H11A	108.9	C22—C23—C24	121.1 (2)
C12—C11—H11A	108.9	C22—C23—Cl1	119.36 (18)
C10—C11—H11B	108.9	C24—C23—Cl1	119.57 (17)
C12—C11—H11B	108.9	C23—C24—C25	119.16 (19)
H11A—C11—H11B	107.7	C23—C24—H24	120.4
C13—C12—C11	110.05 (15)	C25—C24—H24	120.4
C13—C12—H12A	109.7	C24—C25—C20	121.7 (2)
C11—C12—H12A	109.7	C24—C25—H25	119.2
C13—C12—H12B	109.7	C20—C25—H25	119.2
C11—C12—H12B	109.7	C2—O1—H1	109.5
C6—C1—C2—O1	−179.72 (17)	C10—C9—C15—C16	−177.53 (15)
C6—C1—C2—C3	0.8 (3)	C12—C13—C15—C9	−61.04 (19)
O1—C2—C3—C4	179.40 (17)	C18—C13—C15—C9	175.26 (14)
C1—C2—C3—C4	−1.1 (3)	C14A—C13—C15—C9	63.48 (19)
C2—C3—C4—C5	−0.1 (3)	C12—C13—C15—C16	166.24 (15)
C3—C4—C5—C6	1.6 (3)	C18—C13—C15—C16	42.54 (17)
C3—C4—C5—C10	−179.11 (17)	C14A—C13—C15—C16	−69.24 (18)
C2—C1—C6—C5	0.7 (3)	C9—C15—C16—C17	−165.37 (15)
C2—C1—C6—C7	−179.44 (17)	C13—C15—C16—C17	−37.32 (17)
C4—C5—C6—C1	−1.8 (2)	C15—C16—C17—C19	−161.1 (2)
C10—C5—C6—C1	178.84 (16)	C15—C16—C17—C18	17.24 (19)
C4—C5—C6—C7	178.34 (17)	C19—C17—C18—O2	7.3 (3)
C10—C5—C6—C7	−1.0 (3)	C16—C17—C18—O2	−171.3 (2)
C1—C6—C7—C8	170.23 (16)	C19—C17—C18—C13	−172.01 (17)
C5—C6—C7—C8	−9.9 (2)	C16—C17—C18—C13	9.4 (2)
C6—C7—C8—C9	43.0 (2)	C12—C13—C18—O2	30.6 (3)
C7—C8—C9—C15	173.49 (15)	C15—C13—C18—O2	148.9 (2)
C7—C8—C9—C10	−65.58 (19)	C14A—C13—C18—O2	−93.5 (2)
C4—C5—C10—C11	31.8 (2)	C12—C13—C18—C17	−150.10 (16)
C6—C5—C10—C11	−148.94 (16)	C15—C13—C18—C17	−31.83 (18)
C4—C5—C10—C9	159.62 (16)	C14A—C13—C18—C17	85.80 (17)
C6—C5—C10—C9	−21.1 (2)	C18—C17—C19—C20	178.14 (18)
C15—C9—C10—C5	177.72 (14)	C16—C17—C19—C20	−3.7 (4)
C8—C9—C10—C5	53.30 (19)	C17—C19—C20—C25	171.5 (2)
C15—C9—C10—C11	−53.43 (19)	C17—C19—C20—C21	−12.1 (3)
C8—C9—C10—C11	−177.85 (15)	C25—C20—C21—C22	−2.2 (3)
C5—C10—C11—C12	179.77 (15)	C19—C20—C21—C22	−178.62 (19)
C9—C10—C11—C12	52.5 (2)	C20—C21—C22—C23	2.1 (3)
C10—C11—C12—C13	−53.1 (2)	C21—C22—C23—C24	−1.0 (3)
C11—C12—C13—C18	168.38 (16)	C21—C22—C23—Cl1	177.52 (17)
C11—C12—C13—C15	55.4 (2)	C22—C23—C24—C25	0.2 (3)
C11—C12—C13—C14A	−70.4 (2)	Cl1—C23—C24—C25	−178.34 (16)
C8—C9—C15—C13	179.84 (15)	C23—C24—C25—C20	−0.4 (3)
C10—C9—C15—C13	58.55 (18)	C21—C20—C25—C24	1.4 (3)
C8—C9—C15—C16	−56.2 (2)	C19—C20—C25—C24	177.93 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	2.03	2.762 (3)	148
C14A—H14A···O1ii	0.96	2.55	3.454 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82	2.03	2.762 (3)	148
C14A—H14A⋯O1ii	0.96	2.55	3.454 (3)	157

Symmetry codes: (i) ; (ii) .