17a-Allyl-3β-pyrrolidino-17a-aza-D-homoandrost-5-ene monohydrate

The title compound, C₂₆H₄₂N₂·H₂O, a homoandrost-5-ene, contains four fused six-membered rings. Rings A, C and D adopt chair conformations, while ring B adopts an 8β,9α-half-chair conformation.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.050
• wR factor = 0.169
• Data-to-parameter ratio = 7.9

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...      10.00 Ratio

Alert level B
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............      24.98 Deg.
PLAT420_ALERT_2_B D-H Without Acceptor       O1W    -   H2W    ...          ?

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.87
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N23    -   C24     ..       5.62 su
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C26
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT410_ALERT_2_C Short Intra H...H Contact  H12A   ..  H20B    ..       1.95 Ang.
PLAT731_ALERT_1_C Bond    Calc     0.82(7), Rep     0.81(2) ......       3.50 su-Rat
              O1W  -H1W     1.555   1.555

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           24.98
           From the CIF: _reflns_number_total               2424
           Count of symmetry unique reflns         2427
           Completeness (_total/calc)             99.88%
           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

   1 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   7 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
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP97 (Zsolnai, 1997); software used to prepare material for publication: SHELXL97.

17a-Allyl-3β-pyrrolidino-17a-aza-D-homoandrost-5-ene monohydrate

Crystal data

C26H42N2·H2O	Dx = 1.116 Mg m^−3
Mr = 400.63	Melting point: 403 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 6.999 (5) Å	θ = 10–15°
b = 11.569 (5) Å	µ = 0.07 mm^−1
c = 29.441 (10) Å	T = 293 K
V = 2384 (2) Å^3	Plate, green
Z = 4	0.4 × 0.4 × 0.2 mm
F(000) = 888

Data collection

Enraf-Nonius CAD-4 diffractometer	1480 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
Graphite monochromator	θmax = 25.0°, θmin = 2.2°
ω–2θ scans	h = −4→8
Absorption correction: ψ scan (North et al., 1968)	k = 0→13
Tmin = 0.974, Tmax = 0.987	l = 0→34
3348 measured reflections	2 standard reflections every 120 min
2424 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.169	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ^2(Fo^2) + (0.1226P)^2] where P = (Fo^2 + 2Fc^2)/3
2424 reflections	(Δ/σ)max < 0.001
308 parameters	Δρmax = 0.24 e Å^−3
2 restraints	Δρmin = −0.27 e Å^−3

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
N17A	0.8505 (6)	0.1128 (3)	0.08650 (11)	0.0659 (10)
N23	0.2555 (6)	0.1633 (3)	0.39889 (10)	0.0621 (10)
C1	0.3248 (6)	0.1950 (3)	0.27108 (14)	0.0555 (10)
H1A	0.2713	0.2516	0.2503	0.059 (11)*
H1B	0.2833	0.1192	0.2610	0.081 (13)*
C2	0.2454 (7)	0.2168 (3)	0.31768 (13)	0.0610 (11)
H2A	0.1075	0.2089	0.3167	0.067 (13)*
H2B	0.2744	0.2956	0.3265	0.077 (12)*
C3	0.3249 (6)	0.1343 (3)	0.35367 (13)	0.0569 (10)
H3	0.2816	0.0559	0.3463	0.073 (12)*
C4	0.5403 (6)	0.1359 (4)	0.35174 (13)	0.0639 (12)
H4A	0.5850	0.2086	0.3642	0.072 (12)*
H4B	0.5888	0.0744	0.3710	0.075 (13)*
C5	0.6234 (6)	0.1214 (3)	0.30484 (13)	0.0525 (10)
C6	0.7564 (6)	0.0411 (3)	0.29548 (14)	0.0586 (11)
H6	0.7901	−0.0089	0.3189	0.110 (18)*
C7	0.8538 (6)	0.0248 (3)	0.25154 (13)	0.0570 (11)
H7A	0.8119	−0.0477	0.2384	0.066 (12)*
H7B	0.9902	0.0191	0.2569	0.066 (12)*
C8	0.8171 (6)	0.1222 (3)	0.21725 (12)	0.0508 (9)
H8	0.8982	0.1882	0.2252	0.059 (11)*
C9	0.6072 (6)	0.1602 (3)	0.22002 (12)	0.0480 (9)
H9	0.5312	0.0911	0.2135	0.052 (10)*
C10	0.5461 (6)	0.2007 (3)	0.26795 (12)	0.0486 (9)
C11	0.5589 (7)	0.2472 (3)	0.18244 (12)	0.0574 (11)
H11A	0.4231	0.2637	0.1833	0.078 (14)*
H11B	0.6266	0.3188	0.1882	0.058 (11)*
C12	0.6108 (7)	0.2040 (3)	0.13559 (14)	0.0629 (12)
H12A	0.5797	0.2632	0.1135	0.094 (16)*
H12B	0.5341	0.1364	0.1287	0.067 (12)*
C13	0.8209 (7)	0.1728 (3)	0.13103 (14)	0.0581 (10)
C14	0.8681 (6)	0.0825 (3)	0.16815 (13)	0.0557 (11)
H14	0.7845	0.0165	0.1619	0.041 (9)*
C15	1.0721 (8)	0.0361 (4)	0.16355 (15)	0.0749 (14)
H15A	1.1627	0.0985	0.1681	0.108 (19)*
H15B	1.0951	−0.0221	0.1866	0.067 (12)*
C16	1.1006 (8)	−0.0160 (4)	0.11703 (15)	0.0787 (14)
H16A	1.2335	−0.0380	0.1134	0.110 (18)*
H16B	1.0235	−0.0854	0.1144	0.107 (19)*
C17	1.0459 (8)	0.0676 (4)	0.07990 (15)	0.0742 (13)
H17A	1.1356	0.1315	0.0796	0.056 (11)*
H17B	1.0536	0.0289	0.0507	0.098 (16)*
C18	0.9458 (8)	0.2818 (3)	0.13523 (16)	0.0768 (14)
H18A	1.0774	0.2616	0.1306	0.115*
H18B	0.9305	0.3146	0.1650	0.115*
H18C	0.9075	0.3373	0.1127	0.115*
C19	0.6135 (7)	0.3247 (3)	0.27746 (14)	0.0666 (12)
H19A	0.5763	0.3467	0.3076	0.100*
H19B	0.5563	0.3764	0.2559	0.100*
H19C	0.7501	0.3284	0.2748	0.100*
C20	0.7962 (9)	0.1813 (4)	0.04639 (15)	0.0824 (16)
H20A	0.9004	0.2332	0.0389	0.090 (17)*
H20B	0.6860	0.2283	0.0540	0.112 (19)*
C21	0.7499 (9)	0.1108 (5)	0.00561 (17)	0.0924 (16)
H21	0.6724	0.0465	0.0103	0.12 (2)*
C22	0.8049 (11)	0.1288 (6)	−0.0351 (2)	0.111 (2)
H22A	0.8826	0.1918	−0.0417	0.67 (15)*
H22B	0.7673	0.0789	−0.0582	0.23 (5)*
C24	0.0437 (8)	0.1544 (4)	0.40381 (15)	0.0792 (15)
H24A	−0.0028	0.0807	0.3926	0.095 (16)*
H24B	−0.0204	0.2163	0.3877	0.100 (17)*
C25	0.0142 (11)	0.1650 (5)	0.4549 (2)	0.110 (2)
H25A	−0.1020	0.1260	0.4643	0.079 (15)*
H25B	0.0074	0.2454	0.4640	0.17 (3)*
C26	0.1939 (10)	0.1049 (8)	0.4754 (2)	0.119 (2)
H26A	0.2494	0.1520	0.4993	0.17 (3)*
H26B	0.1611	0.0299	0.4879	0.22 (5)*
C27	0.3335 (8)	0.0921 (4)	0.43551 (16)	0.0801 (14)
H27A	0.4599	0.1188	0.4440	0.087 (16)*
H27B	0.3423	0.0119	0.4261	0.107 (18)*
O1W	0.4175 (7)	0.4010 (4)	0.41677 (18)	0.0998 (12)
H1W	0.381 (19)	0.367 (9)	0.394 (2)	0.30 (7)*
H2W	0.291 (5)	0.381 (5)	0.4288 (17)	0.11 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N17A	0.076 (3)	0.0587 (16)	0.063 (2)	0.0124 (19)	0.002 (2)	0.0004 (15)
N23	0.066 (3)	0.0642 (18)	0.057 (2)	−0.0011 (18)	0.0073 (18)	0.0026 (15)
C1	0.049 (3)	0.0551 (19)	0.063 (3)	0.0059 (18)	−0.007 (2)	−0.0063 (18)
C2	0.058 (3)	0.060 (2)	0.065 (3)	0.0097 (19)	−0.003 (2)	−0.0007 (18)
C3	0.054 (3)	0.057 (2)	0.060 (3)	−0.0014 (19)	−0.001 (2)	−0.0027 (17)
C4	0.059 (3)	0.070 (2)	0.062 (3)	0.005 (2)	−0.014 (2)	−0.001 (2)
C5	0.037 (3)	0.0566 (18)	0.064 (3)	−0.0038 (17)	−0.0051 (18)	−0.0051 (17)
C6	0.054 (3)	0.0601 (19)	0.062 (3)	0.001 (2)	−0.005 (2)	0.0064 (19)
C7	0.049 (3)	0.0542 (19)	0.068 (3)	0.0104 (19)	−0.009 (2)	0.0015 (17)
C8	0.053 (3)	0.0439 (15)	0.055 (2)	0.0017 (17)	−0.0120 (18)	−0.0019 (15)
C9	0.041 (3)	0.0463 (15)	0.057 (2)	0.0004 (16)	−0.0054 (17)	0.0020 (15)
C10	0.047 (3)	0.0439 (15)	0.055 (2)	0.0007 (16)	−0.0059 (18)	−0.0047 (15)
C11	0.058 (3)	0.0549 (19)	0.060 (3)	0.014 (2)	−0.004 (2)	0.0022 (17)
C12	0.065 (3)	0.062 (2)	0.062 (3)	0.013 (2)	−0.005 (2)	0.0056 (19)
C13	0.066 (3)	0.0477 (17)	0.061 (3)	0.0059 (19)	−0.006 (2)	0.0058 (16)
C14	0.062 (3)	0.0467 (16)	0.059 (2)	0.0008 (18)	−0.001 (2)	0.0012 (15)
C15	0.075 (4)	0.076 (3)	0.074 (3)	0.024 (3)	0.008 (2)	0.011 (2)
C16	0.076 (4)	0.080 (3)	0.080 (3)	0.027 (3)	0.011 (3)	0.004 (2)
C17	0.076 (4)	0.081 (3)	0.066 (3)	0.012 (3)	0.012 (3)	0.000 (2)
C18	0.091 (4)	0.054 (2)	0.086 (3)	−0.008 (2)	−0.015 (3)	0.009 (2)
C19	0.071 (3)	0.0474 (17)	0.081 (3)	−0.0054 (19)	−0.009 (2)	−0.0141 (18)
C20	0.103 (5)	0.083 (3)	0.061 (3)	0.020 (3)	−0.004 (3)	0.012 (2)
C21	0.102 (5)	0.097 (3)	0.079 (4)	−0.008 (4)	−0.014 (3)	0.005 (3)
C22	0.140 (6)	0.136 (4)	0.059 (3)	0.026 (5)	−0.001 (4)	0.006 (3)
C24	0.091 (5)	0.070 (3)	0.077 (3)	0.002 (3)	0.013 (3)	0.003 (2)
C25	0.128 (6)	0.106 (4)	0.096 (4)	−0.003 (4)	0.031 (4)	0.005 (3)
C26	0.087 (5)	0.182 (7)	0.088 (4)	−0.006 (5)	0.008 (4)	0.009 (5)
C27	0.067 (4)	0.095 (3)	0.079 (3)	0.001 (3)	−0.009 (3)	0.014 (3)
O1W	0.075 (3)	0.099 (2)	0.125 (3)	−0.009 (2)	−0.015 (3)	−0.013 (2)

Geometric parameters (Å, º)

N17A—C20	1.472 (5)	C13—C18	1.540 (6)
N17A—C17	1.477 (6)	C13—C14	1.547 (5)
N17A—C13	1.498 (5)	C14—C15	1.532 (6)
N23—C3	1.457 (5)	C14—H14	0.9800
N23—C27	1.462 (5)	C15—C16	1.510 (6)
N23—C24	1.493 (6)	C15—H15A	0.9700
C1—C2	1.501 (6)	C15—H15B	0.9700
C1—C10	1.553 (6)	C16—C17	1.510 (6)
C1—H1A	0.9700	C16—H16A	0.9700
C1—H1B	0.9700	C16—H16B	0.9700
C2—C3	1.531 (5)	C17—H17A	0.9700
C2—H2A	0.9700	C17—H17B	0.9700
C2—H2B	0.9700	C18—H18A	0.9600
C3—C4	1.509 (6)	C18—H18B	0.9600
C3—H3	0.9800	C18—H18C	0.9600
C4—C5	1.508 (5)	C19—H19A	0.9600
C4—H4A	0.9700	C19—H19B	0.9600
C4—H4B	0.9700	C19—H19C	0.9600
C5—C6	1.344 (5)	C20—C21	1.487 (7)
C5—C10	1.521 (5)	C20—H20A	0.9700
C6—C7	1.474 (6)	C20—H20B	0.9700
C6—H6	0.9300	C21—C22	1.276 (7)
C7—C8	1.534 (5)	C21—H21	0.9300
C7—H7A	0.9700	C22—H22A	0.9300
C7—H7B	0.9700	C22—H22B	0.9300
C8—C9	1.535 (6)	C24—C25	1.522 (7)
C8—C14	1.558 (5)	C24—H24A	0.9700
C8—H8	0.9800	C24—H24B	0.9700
C9—C11	1.533 (5)	C25—C26	1.559 (8)
C9—C10	1.547 (5)	C25—H25A	0.9700
C9—H9	0.9800	C25—H25B	0.9700
C10—C19	1.535 (5)	C26—C27	1.535 (8)
C11—C12	1.511 (6)	C26—H26A	0.9700
C11—H11A	0.9700	C26—H26B	0.9700
C11—H11B	0.9700	C27—H27A	0.9700
C12—C13	1.520 (6)	C27—H27B	0.9700
C12—H12A	0.9700	O1W—H1W	0.81 (2)
C12—H12B	0.9700	O1W—H2W	0.98 (2)
C20—N17A—C17	108.9 (4)	C12—C13—C14	107.7 (3)
C20—N17A—C13	114.6 (3)	C18—C13—C14	112.0 (3)
C17—N17A—C13	114.0 (3)	C15—C14—C13	111.9 (3)
C3—N23—C27	114.8 (4)	C15—C14—C8	113.5 (3)
C3—N23—C24	113.8 (3)	C13—C14—C8	114.1 (3)
C27—N23—C24	105.1 (4)	C15—C14—H14	105.5
C2—C1—C10	114.6 (3)	C13—C14—H14	105.5
C2—C1—H1A	108.6	C8—C14—H14	105.5
C10—C1—H1A	108.6	C16—C15—C14	110.1 (4)
C2—C1—H1B	108.6	C16—C15—H15A	109.6
C10—C1—H1B	108.6	C14—C15—H15A	109.6
H1A—C1—H1B	107.6	C16—C15—H15B	109.6
C1—C2—C3	113.2 (3)	C14—C15—H15B	109.6
C1—C2—H2A	108.9	H15A—C15—H15B	108.2
C3—C2—H2A	108.9	C17—C16—C15	111.5 (4)
C1—C2—H2B	108.9	C17—C16—H16A	109.3
C3—C2—H2B	108.9	C15—C16—H16A	109.3
H2A—C2—H2B	107.8	C17—C16—H16B	109.3
N23—C3—C4	111.4 (4)	C15—C16—H16B	109.3
N23—C3—C2	111.6 (3)	H16A—C16—H16B	108.0
C4—C3—C2	109.3 (4)	N17A—C17—C16	111.5 (4)
N23—C3—H3	108.2	N17A—C17—H17A	109.3
C4—C3—H3	108.2	C16—C17—H17A	109.3
C2—C3—H3	108.2	N17A—C17—H17B	109.3
C5—C4—C3	114.7 (3)	C16—C17—H17B	109.3
C5—C4—H4A	108.6	H17A—C17—H17B	108.0
C3—C4—H4A	108.6	C13—C18—H18A	109.5
C5—C4—H4B	108.6	C13—C18—H18B	109.5
C3—C4—H4B	108.6	H18A—C18—H18B	109.5
H4A—C4—H4B	107.6	C13—C18—H18C	109.5
C6—C5—C4	122.1 (4)	H18A—C18—H18C	109.5
C6—C5—C10	121.1 (4)	H18B—C18—H18C	109.5
C4—C5—C10	116.8 (3)	C10—C19—H19A	109.5
C5—C6—C7	126.0 (4)	C10—C19—H19B	109.5
C5—C6—H6	117.0	H19A—C19—H19B	109.5
C7—C6—H6	117.0	C10—C19—H19C	109.5
C6—C7—C8	114.0 (3)	H19A—C19—H19C	109.5
C6—C7—H7A	108.8	H19B—C19—H19C	109.5
C8—C7—H7A	108.8	N17A—C20—C21	114.1 (4)
C6—C7—H7B	108.8	N17A—C20—H20A	108.7
C8—C7—H7B	108.8	C21—C20—H20A	108.7
H7A—C7—H7B	107.6	N17A—C20—H20B	108.7
C7—C8—C9	109.6 (3)	C21—C20—H20B	108.7
C7—C8—C14	110.9 (3)	H20A—C20—H20B	107.6
C9—C8—C14	110.7 (3)	C22—C21—C20	127.1 (6)
C7—C8—H8	108.5	C22—C21—H21	116.5
C9—C8—H8	108.5	C20—C21—H21	116.5
C14—C8—H8	108.5	C21—C22—H22A	120.0
C11—C9—C8	111.2 (3)	C21—C22—H22B	120.0
C11—C9—C10	113.5 (3)	H22A—C22—H22B	120.0
C8—C9—C10	113.6 (3)	N23—C24—C25	103.0 (5)
C11—C9—H9	106.0	N23—C24—H24A	111.2
C8—C9—H9	106.0	C25—C24—H24A	111.2
C10—C9—H9	106.0	N23—C24—H24B	111.2
C5—C10—C19	108.9 (3)	C25—C24—H24B	111.2
C5—C10—C9	111.7 (3)	H24A—C24—H24B	109.1
C19—C10—C9	111.4 (3)	C24—C25—C26	103.7 (5)
C5—C10—C1	106.7 (3)	C24—C25—H25A	111.0
C19—C10—C1	109.6 (3)	C26—C25—H25A	111.0
C9—C10—C1	108.5 (3)	C24—C25—H25B	111.0
C12—C11—C9	112.9 (3)	C26—C25—H25B	111.0
C12—C11—H11A	109.0	H25A—C25—H25B	109.0
C9—C11—H11A	109.0	C27—C26—C25	105.1 (5)
C12—C11—H11B	109.0	C27—C26—H26A	110.7
C9—C11—H11B	109.0	C25—C26—H26A	110.7
H11A—C11—H11B	107.8	C27—C26—H26B	110.7
C11—C12—C13	113.0 (4)	C25—C26—H26B	110.7
C11—C12—H12A	109.0	H26A—C26—H26B	108.8
C13—C12—H12A	109.0	N23—C27—C26	105.8 (5)
C11—C12—H12B	109.0	N23—C27—H27A	110.6
C13—C12—H12B	109.0	C26—C27—H27A	110.6
H12A—C12—H12B	107.8	N23—C27—H27B	110.6
N17A—C13—C12	108.7 (3)	C26—C27—H27B	110.6
N17A—C13—C18	111.8 (4)	H27A—C27—H27B	108.7
C12—C13—C18	110.3 (3)	H1W—O1W—H2W	84 (9)
N17A—C13—C14	106.0 (3)
C10—C1—C2—C3	−56.7 (5)	C17—N17A—C13—C12	−174.3 (3)
C27—N23—C3—C4	−54.4 (5)	C20—N17A—C13—C18	−62.9 (5)
C24—N23—C3—C4	−175.6 (4)	C17—N17A—C13—C18	63.6 (4)
C27—N23—C3—C2	−176.8 (4)	C20—N17A—C13—C14	174.8 (4)
C24—N23—C3—C2	62.0 (5)	C17—N17A—C13—C14	−58.7 (4)
C1—C2—C3—N23	175.8 (4)	C11—C12—C13—N17A	170.5 (3)
C1—C2—C3—C4	52.2 (5)	C11—C12—C13—C18	−66.5 (4)
N23—C3—C4—C5	−172.7 (3)	C11—C12—C13—C14	56.1 (4)
C2—C3—C4—C5	−49.0 (5)	N17A—C13—C14—C15	58.0 (4)
C3—C4—C5—C6	−127.6 (4)	C12—C13—C14—C15	174.3 (3)
C3—C4—C5—C10	51.1 (5)	C18—C13—C14—C15	−64.2 (4)
C4—C5—C6—C7	−176.2 (4)	N17A—C13—C14—C8	−171.4 (3)
C10—C5—C6—C7	5.2 (6)	C12—C13—C14—C8	−55.1 (4)
C5—C6—C7—C8	9.9 (6)	C18—C13—C14—C8	66.4 (5)
C6—C7—C8—C9	−39.7 (4)	C7—C8—C14—C15	−54.5 (4)
C6—C7—C8—C14	−162.2 (4)	C9—C8—C14—C15	−176.4 (3)
C7—C8—C9—C11	−173.2 (3)	C7—C8—C14—C13	175.7 (4)
C14—C8—C9—C11	−50.6 (4)	C9—C8—C14—C13	53.8 (4)
C7—C8—C9—C10	57.3 (4)	C13—C14—C15—C16	−57.3 (5)
C14—C8—C9—C10	179.9 (3)	C8—C14—C15—C16	171.8 (3)
C6—C5—C10—C19	−112.0 (4)	C14—C15—C16—C17	53.2 (6)
C4—C5—C10—C19	69.4 (4)	C20—N17A—C17—C16	−172.6 (4)
C6—C5—C10—C9	11.4 (5)	C13—N17A—C17—C16	58.0 (4)
C4—C5—C10—C9	−167.2 (3)	C15—C16—C17—N17A	−53.3 (6)
C6—C5—C10—C1	129.8 (4)	C17—N17A—C20—C21	74.5 (6)
C4—C5—C10—C1	−48.8 (4)	C13—N17A—C20—C21	−156.4 (5)
C11—C9—C10—C5	−171.2 (3)	N17A—C20—C21—C22	−135.3 (6)
C8—C9—C10—C5	−42.9 (4)	C3—N23—C24—C25	169.2 (4)
C11—C9—C10—C19	−49.2 (4)	C27—N23—C24—C25	42.8 (5)
C8—C9—C10—C19	79.1 (4)	N23—C24—C25—C26	−33.8 (6)
C11—C9—C10—C1	71.5 (4)	C24—C25—C26—C27	13.6 (7)
C8—C9—C10—C1	−160.3 (3)	C3—N23—C27—C26	−159.8 (5)
C2—C1—C10—C5	51.7 (4)	C24—N23—C27—C26	−34.0 (6)
C2—C1—C10—C19	−66.0 (4)	C25—C26—C27—N23	12.1 (7)
C2—C1—C10—C9	172.3 (3)	H8—C8—C9—H9	−177.0
C8—C9—C11—C12	53.3 (4)	H14—C14—C13—C18	−178.3
C10—C9—C11—C12	−177.2 (3)	H9—C9—C10—C19	−165.0
C9—C11—C12—C13	−57.3 (5)	C19—C10—C13—C18	12.4 (3)
C20—N17A—C13—C12	59.2 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···N23	0.81 (8)	2.52 (10)	3.021 (5)	121 (10)