17-Bromo-16-form­yl-3-methoxy­estra-1,3,5(10),16-tetra­ene

Watanabe, M.; Matsumoto, T.; Mataka, S.; Thiemann, T.

doi:10.1107/S160053680500704X

17-Bromo-16-formyl-3-methoxyestra-1,3,5(10),16-tetraene

M. Watanabe, T. Matsumoto, S. Mataka and T. Thiemann

In the title estrane derivative, C₂₀H₂₃BrO₂, the five-membered ring adopts a conformation that is intermediate between twist and envelope. The C atom of the formyl group and the bromo function are in close proximity. Close intermolecular Br

Br and Br

C contacts are observed in the crystal structure.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680500704X/ya6235sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680500704X/ya6235Isup2.hkl Contains datablock I

CCDC reference: 270579

checkCIF report

Key indicators

Single-crystal X-ray study
T = 123 K
Mean (C-C) = 0.003 Å
R factor = 0.023
wR factor = 0.061
Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.711     0.864
            Tmin and Tmax expected:      0.623     0.864
            RR =      1.141
            Please check that your absorption correction is appropriate.
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large .......       1.14
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT734_ALERT_1_C Contact Calc  3.6165(14), Rep   3.6165(6) ......       2.33 su-Rat
              BR1  -BR1     1.555   2.546
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ..       0.01

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           27.50
           From the CIF: _reflns_number_total               3534
           Count of symmetry unique reflns         2132
           Completeness (_total/calc)            165.76%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1402
           Fraction of Friedel pairs measured     0.658
           Are heavy atom types Z>Si present        yes

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrystalClear (Rigaku Corporation, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: CrystalStructure.

(I) top

Crystal data top

C₂₀H₂₃BrO₂	F(000) = 388.00
M_r = 375.30	D_x = 1.467 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: P 2yb	Cell parameters from 3041 reflections
a = 9.702 (3) Å	θ = 3.6–27.5°
b = 6.093 (2) Å	µ = 2.43 mm⁻¹
c = 14.640 (5) Å	T = 123 K
β = 100.914 (1)°	Platelet, colorless
V = 849.7 (4) Å³	0.20 × 0.18 × 0.06 mm
Z = 2

Data collection top

Rigaku Saturn diffractometer	3354 reflections with I > 2σ(I)
Detector resolution: 7.31 pixels mm^-1	R_int = 0.025
ω scans	θ_max = 27.5°
Absorption correction: multi-scan (Jacobson, 1998)	h = −11→12
T_min = 0.711, T_max = 0.864	k = −7→7
6860 measured reflections	l = −19→18
3534 independent reflections

Refinement top

Refinement on F²	w = 1/[0.0001F_o² + σ(F_o²) + 1.7]/(4F_o²)
R[F² > 2σ(F²)] = 0.023	(Δ/σ)_max < 0.001
wR(F²) = 0.061	Δρ_max = 0.56 e Å⁻³
S = 1.01	Δρ_min = −0.65 e Å⁻³
3534 reflections	Absolute structure: (Flack, 1983), 1422 Friedel pairs
232 parameters	Absolute structure parameter: 0.000 (7)
H-atom parameters constrained

Special details top

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.10215 (2)	−0.10058 (8)	0.516270 (10)	0.02075 (5)
O1	0.9295 (2)	0.3669 (3)	1.14294 (9)	0.0235 (4)
O2	0.2468 (2)	0.4846 (3)	0.36568 (12)	0.0262 (4)
C1	0.6579 (2)	0.0982 (4)	0.9764 (2)	0.0182 (5)
C2	0.7526 (2)	0.1481 (4)	1.0570 (2)	0.0205 (5)
C3	0.8374 (2)	0.3329 (4)	1.0606 (1)	0.0179 (5)
C4	0.8259 (2)	0.4678 (4)	0.9832 (1)	0.0169 (5)
C5	0.7304 (2)	0.4155 (5)	0.90101 (12)	0.0148 (4)
C6	0.7240 (2)	0.5728 (4)	0.8202 (2)	0.0188 (5)
C7	0.6439 (2)	0.4834 (4)	0.7281 (1)	0.0171 (5)
C8	0.5121 (2)	0.3622 (3)	0.74020 (12)	0.0130 (5)
C9	0.5531 (2)	0.1626 (3)	0.8046 (1)	0.0142 (5)
C10	0.6458 (2)	0.2287 (3)	0.8960 (1)	0.0147 (5)
C11	0.4250 (2)	0.0220 (4)	0.8152 (2)	0.0183 (5)
C12	0.3360 (2)	−0.0475 (3)	0.7215 (2)	0.0173 (5)
C13	0.2959 (2)	0.1522 (4)	0.6586 (1)	0.0137 (5)
C14	0.4319 (2)	0.2735 (3)	0.6482 (1)	0.0131 (5)
C15	0.3866 (2)	0.4219 (5)	0.56262 (13)	0.0165 (5)
C16	0.2753 (2)	0.2779 (4)	0.5036 (2)	0.0155 (5)
C17	0.2349 (2)	0.1204 (4)	0.5568 (2)	0.0151 (5)
C18	0.1898 (2)	0.2968 (4)	0.6974 (2)	0.0191 (5)
C19	1.0250 (2)	0.5463 (4)	1.1454 (2)	0.0227 (6)
C20	0.2153 (2)	0.3255 (4)	0.4061 (2)	0.0189 (5)
H1	0.5998	−0.0278	0.9752	0.022*
H2	0.7593	0.0563	1.1101	0.025*
H4	0.8824	0.5958	0.9858	0.020*
H6A	0.8172	0.6068	0.8138	0.021*
H6B	0.6781	0.7029	0.8341	0.022*
H7A	0.7033	0.3845	0.7036	0.020*
H7B	0.6187	0.6013	0.6858	0.020*
H8	0.4536	0.4577	0.7672	0.015*
H9	0.6096	0.0720	0.7737	0.017*
H11A	0.4570	−0.1057	0.8500	0.022*
H11B	0.3675	0.1058	0.8479	0.021*
H12A	0.3890	−0.1465	0.6917	0.020*
H12B	0.2529	−0.1181	0.7316	0.021*
H14	0.4911	0.1651	0.6294	0.015*
H15A	0.4625	0.4516	0.5319	0.019*
H15B	0.3478	0.5563	0.5789	0.020*
H18A	0.1095	0.2124	0.7029	0.023*
H18B	0.1625	0.4162	0.6562	0.023*
H18C	0.2324	0.3515	0.7568	0.024*
H19A	0.9738	0.6799	1.1356	0.026*
H19B	1.0785	0.5276	1.0980	0.026*
H19C	1.0860	0.5505	1.2044	0.026*
H20	0.1478	0.2267	0.3733	0.022*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.01707 (9)	0.0171 (1)	0.0254 (1)	−0.0042 (1)	−0.00300 (7)	−0.0030 (1)
O1	0.0201 (7)	0.0352 (13)	0.0131 (6)	−0.0046 (8)	−0.0019 (5)	0.0034 (8)
O2	0.0270 (9)	0.0314 (9)	0.0192 (8)	−0.0012 (7)	0.0017 (7)	0.0036 (7)
C1	0.0201 (10)	0.0171 (11)	0.0172 (10)	−0.0038 (9)	0.0031 (8)	0.0018 (8)
C2	0.0214 (10)	0.0241 (12)	0.0153 (10)	0.0014 (9)	0.0014 (8)	0.0048 (9)
C3	0.0160 (9)	0.0240 (12)	0.0130 (9)	0.0015 (8)	0.0006 (7)	−0.0003 (8)
C4	0.0157 (9)	0.0175 (11)	0.0170 (10)	−0.0027 (7)	0.0020 (8)	−0.0018 (8)
C5	0.0148 (8)	0.0147 (10)	0.0144 (8)	0.0008 (11)	0.0015 (6)	0.0024 (10)
C6	0.0193 (10)	0.0150 (11)	0.0196 (10)	−0.0043 (8)	−0.0028 (9)	0.0043 (8)
C7	0.0178 (10)	0.0164 (9)	0.0161 (10)	−0.0039 (8)	0.0003 (8)	0.0036 (8)
C8	0.0144 (8)	0.0121 (13)	0.0115 (8)	−0.0016 (8)	−0.0002 (6)	0.0006 (7)
C9	0.0152 (9)	0.0119 (10)	0.0151 (9)	−0.0003 (8)	0.0020 (8)	0.0022 (8)
C10	0.0140 (9)	0.0147 (10)	0.0155 (9)	0.0014 (8)	0.0033 (8)	−0.0000 (8)
C11	0.0173 (10)	0.0190 (12)	0.0180 (10)	−0.0036 (9)	0.0015 (9)	0.0048 (9)
C12	0.0150 (9)	0.0148 (13)	0.0208 (9)	−0.0037 (7)	0.0002 (8)	0.0018 (8)
C13	0.0133 (9)	0.0121 (10)	0.0150 (9)	−0.0011 (8)	0.0014 (7)	0.0006 (8)
C14	0.0124 (9)	0.0125 (10)	0.0134 (9)	−0.0009 (8)	0.0001 (7)	0.0001 (7)
C15	0.0196 (8)	0.0143 (11)	0.0144 (8)	−0.0032 (10)	0.0004 (7)	0.0014 (10)
C16	0.0145 (10)	0.0149 (11)	0.0155 (10)	0.0002 (8)	−0.0015 (8)	−0.0037 (8)
C17	0.0120 (9)	0.0133 (10)	0.0187 (10)	0.0005 (8)	−0.0000 (8)	−0.0035 (8)
C18	0.0160 (10)	0.0224 (11)	0.0187 (10)	0.0008 (9)	0.0031 (8)	−0.0058 (9)
C19	0.0195 (11)	0.0280 (12)	0.0183 (10)	−0.0003 (9)	−0.0019 (9)	−0.0013 (9)
C20	0.0161 (10)	0.0229 (11)	0.0166 (10)	0.0013 (8)	0.0006 (8)	−0.0029 (9)

Geometric parameters (Å, º) top

Br1—C17	1.880 (2)	C16—C20	1.465 (3)
O2—C20	1.205 (3)	C1—H1	0.9500
O1—C3	1.373 (2)	C2—H2	0.9500
O1—C19	1.428 (3)	C4—H4	0.9500
C1—C2	1.385 (3)	C6—H6B	0.9500
C1—C10	1.407 (3)	C6—H6A	0.9500
C2—C3	1.390 (3)	C7—H7B	0.9500
C3—C4	1.388 (3)	C7—H7A	0.9500
C4—C5	1.409 (3)	C8—H8	0.9500
C5—C6	1.514 (3)	C9—H9	0.9500
C5—C10	1.397 (3)	C11—H11A	0.9500
C6—C7	1.523 (3)	C11—H11B	0.9500
C7—C8	1.516 (3)	C12—H12B	0.9500
C8—C9	1.544 (3)	C12—H12A	0.9501
C8—C14	1.521 (3)	C14—H14	0.9500
C9—C10	1.519 (3)	C15—H15A	0.9500
C9—C11	1.541 (3)	C15—H15B	0.9500
C11—C12	1.535 (3)	C18—H18B	0.9500
C12—C13	1.531 (3)	C18—H18A	0.9500
C13—C14	1.545 (3)	C18—H18C	0.9501
C13—C17	1.509 (3)	C19—H19B	0.9500
C13—C18	1.542 (3)	C19—H19A	0.9500
C14—C15	1.540 (3)	C19—H19C	0.9499
C15—C16	1.526 (3)	C20—H20	0.9499
C16—C17	1.340 (3)

Br1···Br1ⁱ	3.6165 (6)	C9···H6B^vii	3.0497
Br1···C12	3.420 (2)	C9···H6B	3.507
Br1···C13	2.960 (2)	C9···H7B	3.3154
Br1···C16	2.880 (2)	C9···H7A	2.6365
Br1···C18	3.572 (2)	C9···H8	2.0651
Br1···C20	3.349 (2)	C9···H11A	2.0538
Br1···C20ⁱ	3.508 (2)	C9···H11B	2.0489
O2···C7ⁱⁱ	3.590 (3)	C9···H12B	3.3721
O2···C7ⁱⁱⁱ	3.578 (3)	C9···H12A	2.7951
O2···C15	2.969 (2)	C9···H14	2.5212
O2···C16	2.351 (3)	C9···H18C	3.2669
O2···C17	3.590 (3)	C10···H1	2.0449
O2···C19^iv	3.541 (3)	C10···H2	3.2921
O1···C2	2.343 (3)	C10···H4	3.2955
O1···C4	2.443 (2)	C10···H6B^vii	3.3599
C1···C3	2.405 (3)	C10···H6B	3.062
C1···C4	2.771 (3)	C10···H6A	3.2062
C1···C5	2.397 (4)	C10···H7A	3.1207
C1···C9	2.559 (3)	C10···H8	2.7648
C1···C11	2.979 (3)	C10···H9	2.0001
C2···C4	2.400 (3)	C10···H11A	2.737
C2···C5	2.780 (3)	C10···H11B	2.7619
C2···C10	2.439 (3)	C11···H1	2.6369
C3···C5	2.424 (3)	C11···H6B^vii	3.1026
C3···C10	2.824 (3)	C11···H8^vii	3.5303
C3···C19	2.385 (3)	C11···H8	2.7735
C4···C6	2.487 (3)	C11···H9	2.0202
C4···C10	2.442 (3)	C11···H12B	2.0591
C4···C19	2.804 (3)	C11···H12A	2.0497
C5···C7	2.545 (3)	C11···H14	3.0386
C5···C8	2.871 (2)	C11···H18A	3.393
C5···C9	2.531 (3)	C11···H18C	2.7657
C6···C8	2.516 (3)	C12···H7B^vii	3.5938
C6···C9	2.984 (3)	C12···H8^vii	3.2479
C6···C10	2.553 (3)	C12···H8	3.3073
C7···O2ⁱⁱ	3.578 (3)	C12···H9	2.7192
C7···O2ⁱⁱⁱ	3.590 (3)	C12···H11A	2.0513
C7···C9	2.495 (3)	C12···H11B	2.0427
C7···C10	2.903 (3)	C12···H14	2.5562
C7···C14	2.515 (3)	C12···H15B^vii	3.2082
C7···C15	3.155 (3)	C12···H18B	3.3347
C7···C20ⁱⁱⁱ	3.329 (3)	C12···H18A	2.68
C8···C10	2.535 (3)	C12···H18C	2.7174
C8···C11	2.563 (3)	C13···H8	2.7232
C8···C12	3.008 (3)	C13···H9	3.2248
C8···C13	2.553 (3)	C13···H11A	3.3326
C8···C15	2.679 (2)	C13···H11B	2.7405
C8···C18	3.096 (3)	C13···H12B	2.0487
C9···C12	2.566 (3)	C13···H12A	2.0481
C9···C13	2.962 (3)	C13···H14	2.0211
C9···C14	2.461 (3)	C13···H15A	3.2428
C10···C11	2.572 (3)	C13···H15B	2.8109
C11···C13	2.523 (3)	C13···H18B	2.0609
C11···C14	2.896 (3)	C13···H18A	2.0661
C11···C18	3.081 (3)	C13···H18C	2.0634
C12···C14	2.494 (3)	C14···H7B	2.683
C12···C17	2.633 (3)	C14···H7A	2.6905
C12···C18	2.519 (3)	C14···H8	2.0498
C13···C15	2.432 (3)	C14···H9	2.5797
C13···C16	2.368 (3)	C14···H11B	3.2665
C14···C16	2.361 (3)	C14···H12B	3.3171
C14···C17	2.312 (3)	C14···H12A	2.6882
C14···C18	2.587 (3)	C14···H15A	2.0873
C15···C17	2.345 (3)	C14···H15Aⁱⁱ	3.5879
C15···C18	3.089 (3)	C14···H15B	2.0858
C15···C20	2.630 (3)	C14···H18B	2.7779
C16···C18	3.104 (3)	C14···H18A	3.3926
C17···C18	2.434 (3)	C14···H18C	2.7687
C17···C20	2.511 (3)	C15···H7B	2.825
C19···O2^v	3.541 (3)	C15···H7A	3.3693
C20···Br1^vi	3.508 (2)	C15···H8	2.9506
C20···C7ⁱⁱ	3.329 (3)	C15···H12A^viii	3.2366
Br1···H12B	3.2162	C15···H14	2.0139
Br1···H12A	3.4225	C15···H14ⁱⁱⁱ	3.573
Br1···H15B^vii	3.1728	C15···H18B	2.7804
Br1···H18B^vii	3.571	C15···H18C	3.4804
Br1···H18Bⁱ	3.2436	C15···H20	3.4689
Br1···H18A	3.321	C16···H7Bⁱⁱ	3.3146
Br1···H20	2.9843	C16···H14	2.6052
Br1···H20ⁱ	3.3298	C16···H15A	2.0744
O2···H6Bⁱⁱ	3.5828	C16···H15Aⁱⁱ	3.3462
O2···H6Aⁱⁱ	3.4596	C16···H15B	2.0719
O2···H7Bⁱⁱ	2.846	C16···H18B	2.7968
O2···H7Aⁱⁱⁱ	2.7176	C16···H20	2.0916
O2···H9ⁱⁱⁱ	2.7324	C17···H12B	2.9201
O2···H14ⁱⁱⁱ	2.7585	C17···H12A	2.7688
O2···H15A	2.9004	C17···H14	2.527
O2···H15B	3.1204	C17···H15A	3.0633
O2···H20	1.8561	C17···H15Aⁱⁱ	3.5791
O2···H19C^iv	2.6031	C17···H15B	2.8678
O1···H2	2.4982	C17···H18B	2.4991
O1···H4	2.6547	C17···H18A	2.7116
O1···H19B	1.9601	C17···H18C	3.2536
O1···H19A	1.9623	C17···H20	2.7367
O1···H19C	1.9616	C18···H8	2.7508
C1···H2	2.0336	C18···H11B	2.7824
C1···H6B^vii	3.2148	C18···H12B	2.6266
C1···H9	2.9197	C18···H12A	3.3306
C1···H11A	2.7201	C18···H14	3.3589
C1···H11B	3.0781	C19···H4	2.4982
C2···H1	2.0264	C18···H15B	2.9772
C2···H4	3.2577	C20···H6Aⁱⁱ	3.4421
C3···H1	3.2576	C20···H7Bⁱⁱ	2.6629
C3···H2	2.0364	C20···H7Aⁱⁱ	3.3018
C3···H4	2.0344	C20···H15A	2.8394
C3···H19B	2.588	C20···H15B	2.9668
C3···H19A	2.6223	C20···H19C^iv	3.2817
C3···H19C	3.1754	H6B···O2ⁱⁱⁱ	3.5828
C4···H2	3.2578	H6B···C1^viii	3.2148
C4···H6B	2.7729	H6B···C9^viii	3.0497
C4···H6A	2.6068	H6B···C10^viii	3.3599
C4···H19B	2.7215	H6B···C11^viii	3.1026
C4···H19A	2.7376	H6A···O2ⁱⁱⁱ	3.4596
C5···H1	3.2555	H6A···C20ⁱⁱⁱ	3.4421
C5···H4	2.0569	H7B···O2ⁱⁱⁱ	2.846
C5···H6B	2.0241	H7B···C12^viii	3.5938
C5···H6A	2.0266	H7B···C16ⁱⁱⁱ	3.3146
C5···H7B	3.3299	H7B···C20ⁱⁱⁱ	2.6629
C5···H7A	2.8581	H7A···O2ⁱⁱ	2.7176
C5···H8	3.0198	H7A···C20ⁱⁱⁱ	3.3018
C5···H9	2.8978	H8···C11^viii	3.5303
C6···H4	2.6168	H8···C12^viii	3.2479
C6···H7B	2.0457	H9···O2ⁱⁱ	2.7324
C6···H7A	2.0352	H9···C1	2.9197
C6···H8	2.6836	H9···C5	2.8978
C6···H9	3.2738	H9···C6^vii	3.2651
C6···H9^viii	3.2651	H9···C6	3.2738
C6···H11A^viii	3.3408	H9···C7	2.6312
C6···H20ⁱⁱⁱ	3.4331	H9···C8	2.0212
C7···H6B	2.0271	H9···C10	2.0001
C7···H6A	2.0407	H9···C11	2.0202
C7···H8	2.0396	H9···C12	2.7192
C7···H9	2.6312	H9···C13	3.2248
C7···H12A^viii	3.315	H9···C14	2.5797
C7···H14	2.6905	H11A···C6^vii	3.3408
C7···H15A	3.0784	H12A···C7^vii	3.315
C7···H15B	3.2933	H12A···C8^vii	3.2515
C7···H20ⁱⁱⁱ	3.1017	H12A···C15^vii	3.2366
C8···H6B	2.8202	H14···O2ⁱⁱ	2.7585
C8···H6A	3.3068	H14···C15ⁱⁱ	3.573
C8···H7B	2.0338	H15A···C14ⁱⁱⁱ	3.5879
C8···H7A	2.0301	H15A···C16ⁱⁱⁱ	3.3462
C8···H9	2.0212	H15A···C17ⁱⁱⁱ	3.5791
C8···H11A	3.3651	H15B···Br1^viii	3.1728
C8···H11B	2.781	H15B···C12^viii	3.2082
C8···H12A	3.3489	H18B···Br1^viii	3.571
C8···H12A^viii	3.2515	H18B···Br1^vi	3.2436
C8···H14	1.9978	H19C···O2^v	2.6031
C8···H15A	3.0449	H19C···C20^v	3.2817
C8···H15B	2.8442	H20···Br1^vi	3.3298
C8···H18B	3.3982	H20···C6ⁱⁱ	3.4331
C8···H18C	2.7712	H20···C7ⁱⁱ	3.1017
C9···H1	2.7134

Br1—C17—C13	121.4 (2)	C3—C4—H4	119.7822
Br1—C17—C16	126.0 (2)	H4—C4—C5	120.1121
O2—C20—C16	123.1 (2)	C5—C6—H6B	108.2519
O1—C3—C2	116.0 (2)	C5—C6—H6A	108.4607
O1—C3—C4	124.4 (2)	H6B—C6—C7	107.8305
C19—O1—C3	116.7 (2)	H6A—C6—C7	108.9831
C1—C2—C3	120.2 (2)	C6—C7—H7B	109.4153
C10—C1—C2	121.7 (2)	C6—C7—H7A	108.5182
C1—C10—C5	117.5 (2)	H6A—C6—H6B	109.4585
C1—C10—C9	121.9 (2)	H7B—C7—C8	108.9697
C2—C3—C4	119.6 (2)	H7A—C7—C8	108.6547
C3—C4—C5	120.1 (2)	C7—C8—H8	109.4750
C4—C5—C10	120.9 (2)	H7A—C7—H7B	109.4650
C4—C5—C6	116.5 (2)	C8—C9—H9	105.8097
C10—C5—C6	122.5 (2)	H8—C8—C9	109.4924
C5—C6—C7	113.8 (2)	H8—C8—C14	109.9200
C5—C10—C9	120.4 (2)	C8—C14—H14	105.5393
C6—C7—C8	111.8 (2)	H9—C9—C10	105.9140
C7—C8—C9	109.2 (2)	H9—C9—C11	105.9247
C7—C8—C14	111.8 (2)	C9—C11—H11A	108.7394
C8—C9—C10	111.7 (2)	C9—C11—H11B	108.3232
C8—C9—C11	112.3 (2)	C11—C12—H12B	109.6565
C14—C8—C9	106.8 (2)	C11—C12—H12A	108.8446
C8—C14—C13	112.7 (2)	H11A—C11—C12	108.9806
C8—C14—C15	122.1 (2)	H11B—C11—C12	108.2549
C11—C9—C10	114.4 (2)	H11B—C11—H11A	109.4603
C9—C11—C12	113.0 (2)	H12B—C12—C13	109.0894
C11—C12—C13	110.7 (2)	H12A—C12—C13	109.0369
C12—C13—C17	120.0 (2)	H12A—C12—H12B	109.4610
C12—C13—C18	110.1 (2)	C13—C14—H14	105.7380
C12—C13—C14	108.4 (2)	C13—C18—H18A	109.6958
C17—C13—C14	98.4 (2)	C13—C18—H18B	109.2509
C18—C13—C14	113.9 (2)	C13—C18—H18C	109.4559
C13—C14—C15	104.1 (2)	C14—C15—H15A	111.6890
C13—C17—C16	112.3 (2)	C14—C15—H15B	111.5595
C18—C13—C17	105.8 (2)	H14—C14—C15	105.4671
C14—C15—C16	100.7 (2)	H15A—C15—C16	111.7243
C15—C16—C17	109.6 (2)	H15B—C15—C16	111.5053
C15—C16—C20	123.1 (2)	H15B—C15—H15A	109.4577
C20—C16—C17	127.0 (2)	C16—C20—H20	118.4236
O2—C20—H20	118.4651	H18A—C18—H18B	109.4733
O1—C19—H19B	109.3606	H18C—C18—H18B	109.4762
O1—C19—H19A	109.5533	H18C—C18—H18A	109.4749
O1—C19—H19C	109.4982	H19A—C19—H19B	109.4771
C1—C2—H2	119.9678	H19C—C19—H19B	109.4676
H1—C1—C2	119.2397	H19C—C19—H19A	109.4703
H1—C1—C10	119.0496	Br1ⁱ—Br1—C20ⁱ	56.06 (4)
H2—C2—C3	119.8420

C19—O1—C3—C2	175.3 (2)	C11—C9—C10—C1	29.1 (3)
C19—O1—C3—C4	−4.1 (3)	C11—C9—C10—C5	−155.6 (2)
C10—C1—C2—C3	1.1 (4)	C8—C9—C11—C12	53.0 (2)
C2—C1—C10—C5	−1.8 (3)	C10—C9—C11—C12	−178.4 (2)
C2—C1—C10—C9	173.6 (2)	C9—C11—C12—C13	−52.6 (2)
C1—C2—C3—O1	−179.0 (2)	C11—C12—C13—C14	55.5 (2)
C1—C2—C3—C4	0.4 (4)	C11—C12—C13—C17	167.3 (2)
O1—C3—C4—C5	178.4 (2)	C11—C12—C13—C18	−69.6 (2)
C2—C3—C4—C5	−1.0 (3)	C12—C13—C14—C8	−62.7 (2)
C3—C4—C5—C6	179.5 (2)	C12—C13—C14—C15	163.0 (2)
C3—C4—C5—C10	0.1 (3)	C17—C13—C14—C8	171.7 (2)
C4—C5—C6—C7	167.4 (2)	C17—C13—C14—C15	37.4 (2)
C10—C5—C6—C7	−13.3 (3)	C18—C13—C14—C8	60.2 (2)
C4—C5—C10—C1	1.2 (3)	C18—C13—C14—C15	−74.1 (2)
C4—C5—C10—C9	−174.3 (2)	C12—C13—C17—Br1	40.9 (3)
C6—C5—C10—C1	−178.1 (2)	C12—C13—C17—C16	−145.4 (2)
C6—C5—C10—C9	6.4 (3)	C14—C13—C17—Br1	157.8 (1)
C5—C6—C7—C8	41.3 (3)	C14—C13—C17—C16	−28.5 (2)
C6—C7—C8—C9	−62.1 (2)	C18—C13—C17—Br1	−84.3 (2)
C6—C7—C8—C14	179.8 (2)	C18—C13—C17—C16	89.4 (2)
C7—C8—C9—C10	53.6 (2)	C8—C14—C15—C16	−162.8 (2)
C7—C8—C9—C11	−176.3 (2)	C13—C14—C15—C16	−34.0 (2)
C14—C8—C9—C10	174.7 (2)	C14—C15—C16—C17	16.9 (2)
C14—C8—C9—C11	−55.2 (2)	C14—C15—C16—C20	−168.7 (2)
C7—C8—C14—C13	−179.1 (2)	C15—C16—C17—Br1	−179.0 (2)
C7—C8—C14—C15	−54.1 (3)	C15—C16—C17—C13	7.6 (3)
C9—C8—C14—C13	61.4 (2)	C20—C16—C17—Br1	6.8 (4)
C9—C8—C14—C15	−173.6 (2)	C20—C16—C17—C13	−166.5 (2)
C8—C9—C10—C1	158.1 (2)	C15—C16—C20—O2	−1.8 (4)
C8—C9—C10—C5	−26.6 (3)	C17—C16—C20—O2	171.6 (2)

Symmetry codes: (i) −x, y−1/2, −z+1; (ii) −x+1, y−1/2, −z+1; (iii) −x+1, y+1/2, −z+1; (iv) x−1, y, z−1; (v) x+1, y, z+1; (vi) −x, y+1/2, −z+1; (vii) x, y−1, z; (viii) x, y+1, z.

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

17-Bromo-16-form­yl-3-methoxy­estra-1,3,5(10),16-tetra­ene

Supporting information

Key indicators

checkCIF/PLATON results

17-Bromo-16-formyl-3-methoxyestra-1,3,5(10),16-tetraene