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In the title compound, C
30H
37ClO
4, the cyclohexene ring
A of the steroid nucleus has a 1α-sofa conformation. The cyclohexane rings adopt chair conformations. The cyclopentane ring adopts a 14β-envelope conformation. The benzylidene group has an
E configuration with respect to the carbonyl group on the cyclopentane ring. The crystal packing is dictated by weak intermolecular C—H
O interactions.
Supporting information
CCDC reference: 611204
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.005 Å
- Disorder in main residue
- R factor = 0.056
- wR factor = 0.153
- Data-to-parameter ratio = 15.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C2
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C31
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10
PLAT301_ALERT_3_C Main Residue Disorder ......................... 5.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.13
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 25.00
From the CIF: _reflns_number_total 4850
Count of symmetry unique reflns 2768
Completeness (_total/calc) 175.22%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 2082
Fraction of Friedel pairs measured 0.752
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 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
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003) and
Qmol (Gans & Shalloway, 2001); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
16-[4-(3-Chloropropoxy)-3-methoxybenzylidene]-4-androstene-3,17-dione
top
Crystal data top
C30H37ClO4 | Dx = 1.203 Mg m−3 |
Mr = 497.05 | Melting point = 438–440 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 4170 reflections |
a = 8.0046 (4) Å | θ = 4.8–39.7° |
b = 17.4763 (9) Å | µ = 0.17 mm−1 |
c = 19.6133 (10) Å | T = 273 K |
V = 2743.7 (2) Å3 | Needle, yellow |
Z = 4 | 0.10 × 0.08 × 0.04 mm |
F(000) = 1064 | |
Data collection top
Bruker SMART APEX CCD area detector diffractometer | 3335 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.030 |
Graphite monochromator | θmax = 25.0°, θmin = 1.6° |
ω scans | h = −9→9 |
20024 measured reflections | k = −20→20 |
4850 independent reflections | l = −23→23 |
Refinement top
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)] = 0.056 | H-atom parameters constrained |
wR(F2) = 0.153 | w = 1/[σ2(Fo2) + (0.0799P)2 + 0.3313P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.001 |
4850 reflections | Δρmax = 0.29 e Å−3 |
320 parameters | Δρmin = −0.16 e Å−3 |
40 restraints | Absolute structure: Flack (1983), 2083 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.00 (13) |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O3 | 0.6009 (5) | 0.1670 (2) | −0.38108 (15) | 0.1491 (12) | |
O17 | −0.0815 (3) | 0.19477 (14) | 0.07792 (13) | 0.1012 (7) | |
O23 | 0.7550 (4) | 0.08399 (17) | 0.24723 (12) | 0.1078 (8) | |
O28 | 0.6916 (4) | 0.13245 (19) | 0.36747 (13) | 0.1242 (9) | |
C1 | 0.2469 (5) | 0.1573 (3) | −0.27176 (19) | 0.1172 (14) | |
H1A | 0.1275 | 0.1505 | −0.2777 | 0.141* | |
H1B | 0.2659 | 0.2098 | −0.2579 | 0.141* | |
C2 | 0.3319 (6) | 0.1440 (3) | −0.3389 (2) | 0.1331 (16) | |
H2A | 0.3005 | 0.0940 | −0.3562 | 0.160* | |
H2B | 0.2940 | 0.1820 | −0.3714 | 0.160* | |
C3 | 0.5153 (7) | 0.1481 (2) | −0.3332 (2) | 0.1092 (12) | |
C4 | 0.5856 (5) | 0.1254 (2) | −0.26801 (18) | 0.0919 (10) | |
H4 | 0.7011 | 0.1274 | −0.2632 | 0.110* | |
C5 | 0.4967 (4) | 0.10190 (18) | −0.21488 (17) | 0.0755 (8) | |
C6 | 0.5812 (4) | 0.0687 (2) | −0.15353 (16) | 0.0856 (9) | |
H6A | 0.7006 | 0.0775 | −0.1570 | 0.103* | |
H6B | 0.5630 | 0.0138 | −0.1528 | 0.103* | |
C7 | 0.5177 (3) | 0.10287 (19) | −0.08764 (15) | 0.0739 (8) | |
H7A | 0.5504 | 0.1562 | −0.0853 | 0.089* | |
H7B | 0.5686 | 0.0764 | −0.0495 | 0.089* | |
C8 | 0.3288 (3) | 0.09701 (16) | −0.08204 (15) | 0.0664 (7) | |
H8 | 0.2971 | 0.0428 | −0.0814 | 0.080* | |
C9 | 0.2484 (3) | 0.13526 (16) | −0.14412 (15) | 0.0711 (7) | |
H9 | 0.2849 | 0.1888 | −0.1429 | 0.085* | |
C10 | 0.3076 (4) | 0.10340 (18) | −0.21430 (16) | 0.0785 (8) | |
C11 | 0.0544 (4) | 0.1375 (2) | −0.13865 (19) | 0.0917 (10) | |
H11A | 0.0102 | 0.1678 | −0.1760 | 0.110* | |
H11B | 0.0111 | 0.0860 | −0.1433 | 0.110* | |
C12 | −0.0062 (4) | 0.1710 (2) | −0.07186 (18) | 0.0892 (10) | |
H12A | −0.1268 | 0.1667 | −0.0693 | 0.107* | |
H12B | 0.0227 | 0.2248 | −0.0698 | 0.107* | |
C13 | 0.0728 (3) | 0.12900 (17) | −0.01147 (17) | 0.0750 (8) | |
C14 | 0.2613 (3) | 0.13515 (15) | −0.01877 (14) | 0.0648 (7) | |
H14 | 0.2835 | 0.1898 | −0.0251 | 0.078* | |
C15 | 0.3302 (4) | 0.11600 (17) | 0.05229 (14) | 0.0729 (7) | |
H15A | 0.3378 | 0.0611 | 0.0591 | 0.087* | |
H15B | 0.4394 | 0.1387 | 0.0593 | 0.087* | |
C16 | 0.2009 (4) | 0.15141 (16) | 0.09886 (17) | 0.0724 (8) | |
C17 | 0.0457 (4) | 0.16361 (18) | 0.05770 (18) | 0.0798 (9) | |
C18 | 0.0068 (4) | 0.04614 (18) | −0.0066 (2) | 0.0967 (11) | |
H18A | 0.0253 | 0.0204 | −0.0491 | 0.145* | |
H18B | −0.1106 | 0.0470 | 0.0033 | 0.145* | |
H18C | 0.0648 | 0.0196 | 0.0291 | 0.145* | |
C19 | 0.2431 (5) | 0.0218 (2) | −0.2260 (2) | 0.1176 (13) | |
H19A | 0.2909 | 0.0016 | −0.2671 | 0.176* | |
H19B | 0.1236 | 0.0227 | −0.2301 | 0.176* | |
H19C | 0.2744 | −0.0099 | −0.1882 | 0.176* | |
C20 | 0.2067 (4) | 0.17147 (17) | 0.16442 (17) | 0.0810 (9) | |
H20 | 0.1097 | 0.1948 | 0.1801 | 0.097* | |
C21 | 0.3354 (4) | 0.16378 (17) | 0.21572 (17) | 0.0788 (8) | |
C22 | 0.4889 (4) | 0.12775 (18) | 0.20450 (16) | 0.0780 (8) | |
H22 | 0.5128 | 0.1088 | 0.1613 | 0.094* | |
C23 | 0.6052 (4) | 0.11945 (19) | 0.25509 (17) | 0.0844 (9) | |
C24 | 0.5702 (5) | 0.1457 (2) | 0.32061 (19) | 0.0963 (10) | |
C25 | 0.4207 (6) | 0.1825 (2) | 0.3323 (2) | 0.1069 (12) | |
H25 | 0.3974 | 0.2020 | 0.3754 | 0.128* | |
C26 | 0.3063 (5) | 0.1905 (2) | 0.2809 (2) | 0.0994 (11) | |
H26 | 0.2054 | 0.2147 | 0.2903 | 0.119* | |
C27 | 0.7956 (5) | 0.0567 (3) | 0.18167 (19) | 0.1138 (13) | |
H27A | 0.9075 | 0.0369 | 0.1819 | 0.171* | |
H27B | 0.7878 | 0.0979 | 0.1494 | 0.171* | |
H27C | 0.7192 | 0.0168 | 0.1691 | 0.171* | |
C29 | 0.6727 (5) | 0.1565 (3) | 0.43644 (18) | 0.1288 (12) | |
H29A | 0.5694 | 0.1366 | 0.4553 | 0.155* | |
H29B | 0.6698 | 0.2119 | 0.4390 | 0.155* | |
Cl1 | 1.1549 (2) | 0.12117 (10) | 0.49276 (8) | 0.1449 (7) | 0.856 (2) |
C30 | 0.8188 (5) | 0.1262 (3) | 0.4752 (2) | 0.1288 (12) | 0.856 (2) |
H30A | 0.8087 | 0.1405 | 0.5228 | 0.155* | 0.856 (2) |
H30B | 0.8199 | 0.0708 | 0.4725 | 0.155* | 0.856 (2) |
Cl1A | 1.0358 (15) | 0.0988 (6) | 0.5365 (5) | 0.1449 (7) | 0.144 (2) |
C30A | 0.8183 (6) | 0.1884 (16) | 0.4743 (12) | 0.1288 (12) | 0.144 (2) |
H30C | 0.8187 | 0.2437 | 0.4701 | 0.155* | 0.144 (2) |
H30D | 0.8083 | 0.1757 | 0.5223 | 0.155* | 0.144 (2) |
C31 | 0.9781 (6) | 0.1570 (4) | 0.4471 (3) | 0.1588 (19) | |
H31A | 0.9767 | 0.2125 | 0.4499 | 0.191* | |
H31B | 0.9876 | 0.1429 | 0.3995 | 0.191* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O3 | 0.180 (3) | 0.176 (3) | 0.0916 (19) | −0.010 (3) | 0.023 (2) | 0.0081 (19) |
O17 | 0.0775 (14) | 0.1021 (16) | 0.1240 (18) | 0.0370 (12) | 0.0197 (14) | 0.0127 (14) |
O23 | 0.0925 (17) | 0.146 (2) | 0.0851 (16) | 0.0231 (16) | 0.0009 (14) | 0.0125 (15) |
O28 | 0.115 (2) | 0.171 (3) | 0.0868 (16) | −0.0004 (19) | −0.0063 (16) | −0.0196 (17) |
C1 | 0.102 (3) | 0.158 (4) | 0.092 (3) | 0.020 (3) | −0.028 (2) | 0.007 (2) |
C2 | 0.137 (4) | 0.174 (5) | 0.088 (3) | 0.001 (3) | −0.028 (3) | 0.007 (3) |
C3 | 0.139 (4) | 0.108 (3) | 0.081 (3) | −0.008 (3) | 0.006 (3) | −0.008 (2) |
C4 | 0.091 (2) | 0.097 (2) | 0.087 (2) | −0.010 (2) | 0.001 (2) | −0.0160 (19) |
C5 | 0.0707 (18) | 0.0759 (19) | 0.0799 (19) | −0.0051 (16) | −0.0032 (17) | −0.0147 (16) |
C6 | 0.0607 (17) | 0.101 (2) | 0.095 (2) | 0.0088 (16) | −0.0036 (17) | −0.0065 (19) |
C7 | 0.0532 (15) | 0.090 (2) | 0.0783 (18) | 0.0106 (14) | −0.0060 (14) | −0.0023 (16) |
C8 | 0.0514 (14) | 0.0624 (15) | 0.0854 (19) | 0.0022 (12) | −0.0070 (14) | 0.0056 (14) |
C9 | 0.0594 (15) | 0.0674 (16) | 0.0864 (19) | −0.0042 (13) | −0.0100 (15) | −0.0039 (15) |
C10 | 0.0718 (18) | 0.0779 (19) | 0.086 (2) | −0.0059 (15) | −0.0173 (16) | −0.0060 (16) |
C11 | 0.0598 (17) | 0.108 (3) | 0.108 (2) | 0.0104 (16) | −0.0182 (17) | −0.004 (2) |
C12 | 0.0522 (15) | 0.101 (2) | 0.114 (3) | 0.0100 (17) | −0.0068 (18) | 0.001 (2) |
C13 | 0.0502 (15) | 0.0720 (18) | 0.103 (2) | 0.0065 (13) | 0.0012 (15) | 0.0043 (17) |
C14 | 0.0510 (14) | 0.0595 (15) | 0.0840 (19) | 0.0018 (12) | −0.0003 (13) | 0.0033 (14) |
C15 | 0.0639 (16) | 0.0693 (17) | 0.0854 (19) | 0.0058 (14) | 0.0019 (15) | 0.0047 (15) |
C16 | 0.0661 (18) | 0.0597 (15) | 0.091 (2) | 0.0095 (13) | 0.0141 (16) | 0.0061 (15) |
C17 | 0.0645 (18) | 0.0681 (18) | 0.107 (2) | 0.0086 (15) | 0.0085 (17) | 0.0102 (17) |
C18 | 0.0691 (19) | 0.083 (2) | 0.138 (3) | −0.0145 (17) | 0.010 (2) | −0.004 (2) |
C19 | 0.105 (3) | 0.109 (3) | 0.138 (3) | −0.030 (2) | 0.000 (3) | −0.044 (2) |
C20 | 0.080 (2) | 0.0694 (18) | 0.093 (2) | 0.0121 (16) | 0.0153 (18) | 0.0026 (16) |
C21 | 0.086 (2) | 0.0644 (17) | 0.086 (2) | 0.0073 (17) | 0.0144 (19) | 0.0002 (16) |
C22 | 0.084 (2) | 0.0756 (19) | 0.0744 (19) | −0.0006 (17) | 0.0103 (17) | 0.0054 (15) |
C23 | 0.087 (2) | 0.084 (2) | 0.081 (2) | −0.0033 (19) | 0.0076 (19) | 0.0064 (17) |
C24 | 0.107 (3) | 0.099 (3) | 0.083 (2) | −0.006 (2) | −0.002 (2) | −0.008 (2) |
C25 | 0.126 (3) | 0.104 (3) | 0.091 (3) | 0.001 (2) | 0.017 (3) | −0.025 (2) |
C26 | 0.110 (3) | 0.091 (2) | 0.097 (3) | 0.015 (2) | 0.012 (2) | −0.009 (2) |
C27 | 0.096 (3) | 0.150 (4) | 0.095 (3) | 0.040 (2) | 0.021 (2) | 0.022 (2) |
C29 | 0.136 (3) | 0.174 (3) | 0.0764 (19) | −0.030 (3) | 0.0004 (15) | −0.018 (2) |
Cl1 | 0.1546 (14) | 0.1579 (12) | 0.1221 (11) | 0.0310 (11) | −0.0352 (10) | −0.0105 (10) |
C30 | 0.136 (3) | 0.174 (3) | 0.0764 (19) | −0.030 (3) | 0.0004 (15) | −0.018 (2) |
Cl1A | 0.1546 (14) | 0.1579 (12) | 0.1221 (11) | 0.0310 (11) | −0.0352 (10) | −0.0105 (10) |
C30A | 0.136 (3) | 0.174 (3) | 0.0764 (19) | −0.030 (3) | 0.0004 (15) | −0.018 (2) |
C31 | 0.153 (4) | 0.191 (5) | 0.133 (4) | −0.016 (4) | −0.024 (3) | −0.013 (4) |
Geometric parameters (Å, º) top
O3—C3 | 1.209 (5) | C14—H14 | 0.98 |
O17—C17 | 1.221 (3) | C15—C16 | 1.513 (4) |
O23—C23 | 1.358 (4) | C15—H15A | 0.97 |
O23—C27 | 1.409 (4) | C15—H15B | 0.97 |
O28—C24 | 1.358 (4) | C16—C20 | 1.334 (4) |
O28—C29 | 1.425 (4) | C16—C17 | 1.497 (4) |
C1—C2 | 1.501 (6) | C18—H18A | 0.96 |
C1—C10 | 1.547 (5) | C18—H18B | 0.96 |
C1—H1A | 0.97 | C18—H18C | 0.96 |
C1—H1B | 0.97 | C19—H19A | 0.96 |
C2—C3 | 1.474 (6) | C19—H19B | 0.96 |
C2—H2A | 0.97 | C19—H19C | 0.96 |
C2—H2B | 0.97 | C20—C21 | 1.446 (5) |
C3—C4 | 1.451 (5) | C20—H20 | 0.93 |
C4—C5 | 1.327 (4) | C21—C26 | 1.381 (5) |
C4—H4 | 0.93 | C21—C22 | 1.398 (5) |
C5—C6 | 1.498 (4) | C22—C23 | 1.368 (5) |
C5—C10 | 1.514 (5) | C22—H22 | 0.93 |
C6—C7 | 1.512 (4) | C23—C24 | 1.393 (5) |
C6—H6A | 0.97 | C24—C25 | 1.378 (5) |
C6—H6B | 0.97 | C25—C26 | 1.369 (5) |
C7—C8 | 1.520 (4) | C25—H25 | 0.93 |
C7—H7A | 0.97 | C26—H26 | 0.93 |
C7—H7B | 0.97 | C27—H27A | 0.96 |
C8—C14 | 1.509 (4) | C27—H27B | 0.96 |
C8—C9 | 1.531 (4) | C27—H27C | 0.96 |
C8—H8 | 0.98 | C29—C30A | 1.4900 (10) |
C9—C11 | 1.557 (4) | C29—C30 | 1.4921 (10) |
C9—C10 | 1.559 (4) | C29—H29A | 0.97 |
C9—H9 | 0.98 | C29—H29B | 0.97 |
C10—C19 | 1.534 (5) | Cl1—C31 | 1.788 (6) |
C11—C12 | 1.514 (5) | C30—C31 | 1.4898 (10) |
C11—H11A | 0.97 | C30—H30A | 0.97 |
C11—H11B | 0.97 | C30—H30B | 0.97 |
C12—C13 | 1.530 (4) | Cl1A—C31 | 2.079 (11) |
C12—H12A | 0.97 | C30A—C31 | 1.4899 (10) |
C12—H12B | 0.97 | C30A—H30C | 0.97 |
C13—C17 | 1.501 (5) | C30A—H30D | 0.97 |
C13—C14 | 1.519 (4) | C31—H31A | 0.97 |
C13—C18 | 1.544 (4) | C31—H31B | 0.97 |
C14—C15 | 1.536 (4) | | |
| | | |
C23—O23—C27 | 117.5 (3) | C14—C15—H15B | 111.3 |
C24—O28—C29 | 121.1 (3) | H15A—C15—H15B | 109.2 |
C2—C1—C10 | 113.8 (3) | C20—C16—C17 | 120.8 (3) |
C2—C1—H1A | 108.8 | C20—C16—C15 | 131.7 (3) |
C10—C1—H1A | 108.8 | C17—C16—C15 | 107.5 (3) |
C2—C1—H1B | 108.8 | O17—C17—C16 | 125.5 (3) |
C10—C1—H1B | 108.8 | O17—C17—C13 | 126.4 (3) |
H1A—C1—H1B | 107.7 | C16—C17—C13 | 108.1 (2) |
C3—C2—C1 | 112.1 (4) | C13—C18—H18A | 109.5 |
C3—C2—H2A | 109.2 | C13—C18—H18B | 109.5 |
C1—C2—H2A | 109.2 | H18A—C18—H18B | 109.5 |
C3—C2—H2B | 109.2 | C13—C18—H18C | 109.5 |
C1—C2—H2B | 109.2 | H18A—C18—H18C | 109.5 |
H2A—C2—H2B | 107.9 | H18B—C18—H18C | 109.5 |
O3—C3—C4 | 122.6 (4) | C10—C19—H19A | 109.5 |
O3—C3—C2 | 121.2 (4) | C10—C19—H19B | 109.5 |
C4—C3—C2 | 116.1 (4) | H19A—C19—H19B | 109.5 |
C5—C4—C3 | 124.6 (4) | C10—C19—H19C | 109.5 |
C5—C4—H4 | 117.7 | H19A—C19—H19C | 109.5 |
C3—C4—H4 | 117.7 | H19B—C19—H19C | 109.5 |
C4—C5—C6 | 120.6 (3) | C16—C20—C21 | 132.2 (3) |
C4—C5—C10 | 122.5 (3) | C16—C20—H20 | 113.9 |
C6—C5—C10 | 116.9 (3) | C21—C20—H20 | 113.9 |
C5—C6—C7 | 112.4 (3) | C26—C21—C22 | 116.5 (3) |
C5—C6—H6A | 109.1 | C26—C21—C20 | 119.5 (3) |
C7—C6—H6A | 109.1 | C22—C21—C20 | 123.9 (3) |
C5—C6—H6B | 109.1 | C23—C22—C21 | 122.1 (3) |
C7—C6—H6B | 109.1 | C23—C22—H22 | 118.9 |
H6A—C6—H6B | 107.9 | C21—C22—H22 | 118.9 |
C6—C7—C8 | 111.7 (3) | O23—C23—C22 | 124.5 (3) |
C6—C7—H7A | 109.3 | O23—C23—C24 | 115.6 (3) |
C8—C7—H7A | 109.3 | C22—C23—C24 | 119.8 (3) |
C6—C7—H7B | 109.3 | O28—C24—C25 | 126.1 (4) |
C8—C7—H7B | 109.3 | O28—C24—C23 | 115.1 (4) |
H7A—C7—H7B | 107.9 | C25—C24—C23 | 118.8 (4) |
C14—C8—C7 | 112.7 (2) | C26—C25—C24 | 120.4 (3) |
C14—C8—C9 | 108.1 (2) | C26—C25—H25 | 119.8 |
C7—C8—C9 | 109.4 (2) | C24—C25—H25 | 119.8 |
C14—C8—H8 | 108.9 | C25—C26—C21 | 122.3 (4) |
C7—C8—H8 | 108.9 | C25—C26—H26 | 118.8 |
C9—C8—H8 | 108.9 | C21—C26—H26 | 118.8 |
C8—C9—C11 | 112.1 (3) | O23—C27—H27A | 109.5 |
C8—C9—C10 | 114.8 (2) | O23—C27—H27B | 109.5 |
C11—C9—C10 | 111.9 (2) | H27A—C27—H27B | 109.5 |
C8—C9—H9 | 105.8 | O23—C27—H27C | 109.5 |
C11—C9—H9 | 105.8 | H27A—C27—H27C | 109.5 |
C10—C9—H9 | 105.8 | H27B—C27—H27C | 109.5 |
C5—C10—C19 | 108.6 (3) | O28—C29—C30A | 120.0 (7) |
C5—C10—C1 | 108.6 (3) | O28—C29—C30 | 107.2 (3) |
C19—C10—C1 | 110.5 (3) | O28—C29—H29A | 110.3 |
C5—C10—C9 | 108.5 (2) | C30A—C29—H29A | 127.7 |
C19—C10—C9 | 111.2 (3) | C30—C29—H29A | 110.3 |
C1—C10—C9 | 109.3 (3) | O28—C29—H29B | 110.3 |
C12—C11—C9 | 112.9 (3) | C30A—C29—H29B | 67.6 |
C12—C11—H11A | 109.0 | C30—C29—H29B | 110.3 |
C9—C11—H11A | 109.0 | H29A—C29—H29B | 108.5 |
C12—C11—H11B | 109.0 | C31—C30—C29 | 110.7 (4) |
C9—C11—H11B | 109.0 | C31—C30—H30A | 109.5 |
H11A—C11—H11B | 107.8 | C29—C30—H30A | 109.5 |
C11—C12—C13 | 110.6 (3) | C31—C30—H30B | 109.5 |
C11—C12—H12A | 109.5 | C29—C30—H30B | 109.5 |
C13—C12—H12A | 109.5 | H30A—C30—H30B | 108.1 |
C11—C12—H12B | 109.5 | C31—C30A—C29 | 110.8 (4) |
C13—C12—H12B | 109.5 | C31—C30A—H30C | 109.5 |
H12A—C12—H12B | 108.1 | C29—C30A—H30C | 109.5 |
C17—C13—C14 | 101.5 (2) | C31—C30A—H30D | 109.5 |
C17—C13—C12 | 116.5 (3) | C29—C30A—H30D | 109.5 |
C14—C13—C12 | 107.7 (2) | H30C—C30A—H30D | 108.1 |
C17—C13—C18 | 105.8 (3) | C30—C31—Cl1 | 111.4 (4) |
C14—C13—C18 | 114.3 (2) | C30A—C31—Cl1 | 129.0 (11) |
C12—C13—C18 | 110.9 (3) | C30—C31—Cl1A | 72.6 (4) |
C8—C14—C13 | 113.7 (2) | C30A—C31—Cl1A | 94.0 (13) |
C8—C14—C15 | 121.4 (2) | C30—C31—H31A | 109.3 |
C13—C14—C15 | 104.8 (2) | C30A—C31—H31A | 66.6 |
C8—C14—H14 | 105.2 | Cl1—C31—H31A | 109.3 |
C13—C14—H14 | 105.2 | Cl1A—C31—H31A | 116.4 |
C15—C14—H14 | 105.2 | C30—C31—H31B | 109.3 |
C16—C15—C14 | 102.3 (2) | C30A—C31—H31B | 120.4 |
C16—C15—H15A | 111.3 | Cl1—C31—H31B | 109.3 |
C14—C15—H15A | 111.3 | Cl1A—C31—H31B | 132.1 |
C16—C15—H15B | 111.3 | H31A—C31—H31B | 108.0 |
| | | |
C10—C1—C2—C3 | −54.6 (6) | C13—C14—C15—C16 | −36.2 (3) |
C1—C2—C3—O3 | −152.3 (4) | C14—C15—C16—C20 | −160.8 (3) |
C1—C2—C3—C4 | 30.0 (6) | C14—C15—C16—C17 | 18.7 (3) |
O3—C3—C4—C5 | −177.7 (4) | C20—C16—C17—O17 | 3.6 (5) |
C2—C3—C4—C5 | −0.1 (6) | C15—C16—C17—O17 | −176.0 (3) |
C3—C4—C5—C6 | 170.8 (3) | C20—C16—C17—C13 | −174.9 (3) |
C3—C4—C5—C10 | −6.0 (5) | C15—C16—C17—C13 | 5.5 (3) |
C4—C5—C6—C7 | 132.3 (3) | C14—C13—C17—O17 | 154.0 (3) |
C10—C5—C6—C7 | −50.7 (4) | C12—C13—C17—O17 | 37.3 (5) |
C5—C6—C7—C8 | 53.9 (4) | C18—C13—C17—O17 | −86.4 (4) |
C6—C7—C8—C14 | −176.4 (3) | C14—C13—C17—C16 | −27.6 (3) |
C6—C7—C8—C9 | −56.1 (3) | C12—C13—C17—C16 | −144.2 (3) |
C14—C8—C9—C11 | −52.0 (3) | C18—C13—C17—C16 | 92.0 (3) |
C7—C8—C9—C11 | −175.1 (3) | C17—C16—C20—C21 | 177.4 (3) |
C14—C8—C9—C10 | 178.9 (2) | C15—C16—C20—C21 | −3.2 (6) |
C7—C8—C9—C10 | 55.8 (3) | C16—C20—C21—C26 | 179.9 (3) |
C4—C5—C10—C19 | 102.9 (4) | C16—C20—C21—C22 | −2.7 (5) |
C6—C5—C10—C19 | −74.0 (4) | C26—C21—C22—C23 | −0.3 (5) |
C4—C5—C10—C1 | −17.4 (4) | C20—C21—C22—C23 | −177.8 (3) |
C6—C5—C10—C1 | 165.7 (3) | C27—O23—C23—C22 | 2.7 (5) |
C4—C5—C10—C9 | −136.1 (3) | C27—O23—C23—C24 | −179.8 (3) |
C6—C5—C10—C9 | 47.0 (4) | C21—C22—C23—O23 | 179.0 (3) |
C2—C1—C10—C5 | 47.0 (5) | C21—C22—C23—C24 | 1.6 (5) |
C2—C1—C10—C19 | −72.0 (5) | C29—O28—C24—C25 | 0.4 (6) |
C2—C1—C10—C9 | 165.2 (3) | C29—O28—C24—C23 | 179.8 (4) |
C8—C9—C10—C5 | −49.9 (3) | O23—C23—C24—O28 | 0.3 (5) |
C11—C9—C10—C5 | −179.1 (3) | C22—C23—C24—O28 | 177.9 (3) |
C8—C9—C10—C19 | 69.5 (3) | O23—C23—C24—C25 | 179.8 (3) |
C11—C9—C10—C19 | −59.7 (4) | C22—C23—C24—C25 | −2.6 (5) |
C8—C9—C10—C1 | −168.2 (3) | O28—C24—C25—C26 | −178.2 (4) |
C11—C9—C10—C1 | 62.7 (4) | C23—C24—C25—C26 | 2.4 (6) |
C8—C9—C11—C12 | 51.5 (4) | C24—C25—C26—C21 | −1.1 (6) |
C10—C9—C11—C12 | −177.9 (3) | C22—C21—C26—C25 | 0.1 (5) |
C9—C11—C12—C13 | −53.9 (4) | C20—C21—C26—C25 | 177.7 (3) |
C11—C12—C13—C17 | 170.7 (3) | C24—O28—C29—C30A | −140.8 (15) |
C11—C12—C13—C14 | 57.5 (3) | C24—O28—C29—C30 | 174.3 (4) |
C11—C12—C13—C18 | −68.2 (3) | O28—C29—C30—C31 | 60.5 (6) |
C7—C8—C14—C13 | −179.1 (2) | C30A—C29—C30—C31 | −55.4 (11) |
C9—C8—C14—C13 | 59.9 (3) | O28—C29—C30A—C31 | −28 (3) |
C7—C8—C14—C15 | −52.6 (4) | C30—C29—C30A—C31 | 55.4 (11) |
C9—C8—C14—C15 | −173.5 (2) | C29—C30—C31—C30A | 55.3 (11) |
C17—C13—C14—C8 | 174.3 (2) | C29—C30—C31—Cl1 | −179.8 (4) |
C12—C13—C14—C8 | −62.8 (3) | C29—C30—C31—Cl1A | 171.8 (5) |
C18—C13—C14—C8 | 60.9 (4) | C29—C30A—C31—C30 | −55.5 (11) |
C17—C13—C14—C15 | 39.4 (3) | C29—C30A—C31—Cl1 | −135.0 (13) |
C12—C13—C14—C15 | 162.4 (2) | C29—C30A—C31—Cl1A | −114 (2) |
C18—C13—C14—C15 | −74.0 (3) | C19—C10—C13—C18 | 5.2 (3) |
C8—C14—C15—C16 | −166.7 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···O17i | 0.98 | 2.51 | 3.430 (3) | 156 |
C27—H27B···O17ii | 0.96 | 2.43 | 3.306 (5) | 151 |
C30—H30A···O3iii | 0.97 | 2.56 | 3.390 (6) | 144 |
Symmetry codes: (i) x+1/2, −y+1/2, −z; (ii) x+1, y, z; (iii) x, y, z+1. |
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