20-Di­methyl­amino-3α-methyl­amino-5α-pregnane

In the title mol­ecule, C₂₄H₄₄N₂, also known as pachys­amine A, all four rings are trans fused. The cylo­hexane rings adopt chair conformations and the cyclo­pentane ring a half-chair form. The methyl­amino and di­methyl­amino­ethyl substituents are equatorially attached. The crystal structure is stabilized by van der Waals forces.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.058
• wR factor = 0.159
• Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.59 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.22 Ratio
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         N2
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1     ...          ?

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           27.48
           From the CIF: _reflns_number_total               2766
           Count of symmetry unique reflns         2780
           Completeness (_total/calc)             99.50%
           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
   5 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

[17-(1-Dimethylamino-ethyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a] phenanthren-3-yl]-methyl-amine

Crystal data

C24H44N2	F(000) = 404
Mr = 360.61	Dx = 1.079 Mg m^−3
Monoclinic, P21	Melting point: 444-447 K K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 12.664 (3) Å	Cell parameters from 2500 reflections
b = 6.4003 (15) Å	θ = 1.5–27.5°
c = 13.801 (3) Å	µ = 0.06 mm^−1
β = 97.015 (5)°	T = 293 K
V = 1110.2 (4) Å^3	Block, colourless
Z = 2	0.54 × 0.35 × 0.18 mm

Data collection

Siemmens SMART CCD area-detector diffractometer	2766 independent reflections
Radiation source: fine-focus sealed tube	2192 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
Detector resolution: 8.33 pixels mm^-1	θmax = 27.5°, θmin = 1.5°
ω scans	h = −16→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −8→8
Tmin = 0.967, Tmax = 0.989	l = −17→17
7516 measured reflections

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0963P)^2 + 0.0365P] where P = (Fo^2 + 2Fc^2)/3
2766 reflections	(Δ/σ)max = 0.001
238 parameters	Δρmax = 0.22 e Å^−3
1 restraint	Δρmin = −0.19 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
N1	0.9730 (2)	0.5665 (5)	0.55509 (17)	0.0729 (7)
H1	0.958 (3)	0.675 (7)	0.521 (2)	0.087 (12)*
N2	0.18598 (19)	−0.1242 (5)	0.92921 (18)	0.0780 (8)
C1	0.6839 (2)	0.4974 (4)	0.59824 (18)	0.0565 (6)
H1A	0.6202	0.5015	0.5516	0.068*
H1B	0.6771	0.6042	0.6470	0.068*
C2	0.7792 (2)	0.5484 (4)	0.54564 (17)	0.0620 (7)
H2A	0.7809	0.4524	0.4915	0.074*
H2B	0.7711	0.6886	0.5191	0.074*
C3	0.8834 (2)	0.5346 (5)	0.61124 (17)	0.0603 (7)
H3	0.8848	0.6455	0.6603	0.072*
C4	0.8932 (2)	0.3281 (5)	0.66320 (18)	0.0637 (7)
H4A	0.9568	0.3288	0.7101	0.076*
H4B	0.9008	0.2182	0.6162	0.076*
C5	0.79699 (19)	0.2810 (5)	0.71627 (16)	0.0543 (6)
H5	0.7927	0.3946	0.7633	0.065*
C6	0.8123 (2)	0.0809 (6)	0.7756 (2)	0.0752 (9)
H6A	0.8173	−0.0364	0.7318	0.090*
H6B	0.8785	0.0890	0.8189	0.090*
C7	0.7211 (2)	0.0446 (6)	0.83532 (19)	0.0731 (9)
H7A	0.7304	−0.0899	0.8676	0.088*
H7B	0.7226	0.1514	0.8853	0.088*
C8	0.61413 (19)	0.0494 (4)	0.77268 (16)	0.0510 (6)
H8	0.6107	−0.0690	0.7273	0.061*
C9	0.60032 (18)	0.2527 (4)	0.71252 (15)	0.0457 (5)
H9	0.6067	0.3676	0.7598	0.055*
C10	0.6912 (2)	0.2830 (4)	0.64841 (14)	0.0478 (5)
C11	0.4885 (2)	0.2677 (5)	0.65746 (17)	0.0586 (6)
H11A	0.4796	0.4049	0.6277	0.070*
H11B	0.4817	0.1652	0.6053	0.070*
C12	0.3998 (2)	0.2326 (4)	0.72083 (19)	0.0562 (6)
H12A	0.3318	0.2336	0.6799	0.067*
H12B	0.3997	0.3463	0.7673	0.067*
C13	0.41254 (18)	0.0262 (4)	0.77598 (15)	0.0474 (5)
C14	0.52355 (18)	0.0293 (4)	0.83415 (14)	0.0501 (6)
H14	0.5263	0.1546	0.8752	0.060*
C15	0.5230 (2)	−0.1557 (6)	0.90295 (19)	0.0699 (8)
H15A	0.5731	−0.1349	0.9612	0.084*
H15B	0.5408	−0.2840	0.8712	0.084*
C16	0.4088 (2)	−0.1621 (6)	0.92793 (19)	0.0707 (8)
H16A	0.4069	−0.1245	0.9958	0.085*
H16B	0.3795	−0.3015	0.9175	0.085*
C17	0.34384 (19)	−0.0044 (4)	0.86039 (15)	0.0531 (6)
H17	0.3442	0.1284	0.8958	0.064*
C18	0.3974 (2)	−0.1580 (5)	0.70505 (19)	0.0641 (7)
H18A	0.4504	−0.1524	0.6610	0.096*
H18B	0.3279	−0.1506	0.6686	0.096*
H18C	0.4043	−0.2866	0.7411	0.096*
C19	0.6865 (3)	0.1130 (5)	0.57007 (18)	0.0660 (7)
H19A	0.7489	0.1209	0.5372	0.099*
H19B	0.6244	0.1333	0.5237	0.099*
H19C	0.6831	−0.0217	0.6001	0.099*
C20	0.2285 (2)	−0.0729 (5)	0.83816 (18)	0.0623 (7)
H20	0.2290	−0.2033	0.8010	0.075*
C21	0.1607 (2)	0.0809 (7)	0.7739 (2)	0.0883 (11)
H21A	0.0875	0.0387	0.7687	0.133*
H21B	0.1836	0.0833	0.7101	0.133*
H21C	0.1682	0.2179	0.8023	0.133*
C22	0.1661 (3)	0.0548 (10)	0.9872 (3)	0.1177 (17)
H22A	0.1437	0.0094	1.0477	0.177*
H22B	0.1113	0.1389	0.9523	0.177*
H22C	0.2301	0.1358	1.0002	0.177*
C23	0.0962 (3)	−0.2612 (9)	0.9149 (3)	0.1112 (15)
H23A	0.0705	−0.2872	0.9764	0.167*
H23B	0.1169	−0.3909	0.8877	0.167*
H23C	0.0409	−0.1975	0.8709	0.167*
C24	1.0740 (3)	0.5889 (8)	0.6138 (2)	0.0938 (12)
H24A	1.1244	0.6488	0.5752	0.141*
H24B	1.0989	0.4542	0.6373	0.141*
H24C	1.0664	0.6786	0.6683	0.141*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0857 (17)	0.0774 (19)	0.0582 (13)	−0.0115 (15)	0.0189 (12)	0.0103 (14)
N2	0.0628 (13)	0.101 (2)	0.0707 (13)	−0.0016 (15)	0.0124 (11)	0.0068 (16)
C1	0.0730 (16)	0.0430 (13)	0.0543 (12)	0.0098 (12)	0.0112 (11)	0.0103 (11)
C2	0.0873 (18)	0.0454 (14)	0.0555 (12)	0.0041 (13)	0.0179 (13)	0.0106 (11)
C3	0.0799 (17)	0.0563 (15)	0.0475 (11)	−0.0047 (14)	0.0190 (11)	−0.0024 (12)
C4	0.0637 (14)	0.074 (2)	0.0550 (12)	0.0060 (14)	0.0153 (11)	0.0108 (14)
C5	0.0594 (13)	0.0587 (15)	0.0460 (10)	0.0083 (12)	0.0107 (10)	0.0080 (12)
C6	0.0605 (15)	0.095 (2)	0.0716 (15)	0.0204 (16)	0.0157 (13)	0.0376 (17)
C7	0.0578 (14)	0.096 (2)	0.0662 (14)	0.0157 (15)	0.0099 (12)	0.0396 (17)
C8	0.0586 (13)	0.0504 (14)	0.0445 (10)	0.0124 (11)	0.0083 (9)	0.0118 (10)
C9	0.0578 (13)	0.0376 (11)	0.0412 (10)	0.0072 (10)	0.0047 (9)	−0.0006 (9)
C10	0.0659 (13)	0.0378 (12)	0.0410 (10)	0.0080 (10)	0.0110 (10)	0.0021 (10)
C11	0.0681 (15)	0.0523 (14)	0.0537 (12)	0.0096 (13)	0.0007 (11)	0.0139 (12)
C12	0.0575 (14)	0.0469 (15)	0.0622 (13)	0.0099 (12)	−0.0005 (11)	0.0086 (11)
C13	0.0582 (12)	0.0397 (12)	0.0436 (10)	0.0074 (11)	0.0032 (9)	−0.0021 (10)
C14	0.0556 (12)	0.0515 (14)	0.0425 (10)	0.0076 (12)	0.0038 (9)	0.0061 (11)
C15	0.0642 (15)	0.086 (2)	0.0599 (13)	0.0104 (16)	0.0085 (12)	0.0306 (16)
C16	0.0617 (15)	0.089 (2)	0.0610 (14)	0.0027 (16)	0.0061 (12)	0.0228 (16)
C17	0.0602 (14)	0.0509 (14)	0.0476 (11)	0.0034 (12)	0.0040 (10)	−0.0034 (11)
C18	0.0845 (18)	0.0518 (15)	0.0577 (13)	−0.0062 (14)	0.0152 (13)	−0.0080 (12)
C19	0.094 (2)	0.0513 (15)	0.0565 (13)	−0.0016 (15)	0.0246 (13)	−0.0075 (12)
C20	0.0589 (14)	0.0659 (17)	0.0612 (13)	0.0019 (13)	0.0036 (12)	−0.0006 (13)
C21	0.0638 (17)	0.104 (3)	0.0948 (19)	0.0047 (19)	−0.0009 (16)	0.022 (2)
C22	0.099 (3)	0.164 (5)	0.099 (2)	0.001 (3)	0.047 (2)	−0.027 (3)
C23	0.078 (2)	0.144 (4)	0.113 (3)	−0.025 (3)	0.019 (2)	0.025 (3)
C24	0.086 (2)	0.119 (3)	0.0795 (18)	−0.033 (2)	0.0202 (17)	0.010 (2)

Geometric parameters (Å, º)

N1—C24	1.436 (4)	C12—C13	1.523 (3)
N1—C3	1.465 (3)	C12—H12A	0.97
N1—H1	0.84 (4)	C12—H12B	0.97
N2—C23	1.430 (5)	C13—C18	1.529 (3)
N2—C22	1.437 (6)	C13—C14	1.531 (3)
N2—C20	1.464 (4)	C13—C17	1.549 (3)
C1—C2	1.518 (4)	C14—C15	1.519 (4)
C1—C10	1.534 (3)	C14—H14	0.98
C1—H1A	0.97	C15—C16	1.528 (4)
C1—H1B	0.97	C15—H15A	0.97
C2—C3	1.508 (4)	C15—H15B	0.97
C2—H2A	0.97	C16—C17	1.542 (4)
C2—H2B	0.97	C16—H16A	0.97
C3—C4	1.501 (4)	C16—H16B	0.97
C3—H3	0.98	C17—C20	1.520 (4)
C4—C5	1.526 (3)	C17—H17	0.98
C4—H4A	0.97	C18—H18A	0.96
C4—H4B	0.97	C18—H18B	0.96
C5—C6	1.519 (4)	C18—H18C	0.96
C5—C10	1.538 (3)	C19—H19A	0.96
C5—H5	0.98	C19—H19B	0.96
C6—C7	1.517 (4)	C19—H19C	0.96
C6—H6A	0.97	C20—C21	1.519 (4)
C6—H6B	0.97	C20—H20	0.98
C7—C8	1.516 (3)	C21—H21A	0.96
C7—H7A	0.97	C21—H21B	0.96
C7—H7B	0.97	C21—H21C	0.96
C8—C14	1.513 (3)	C22—H22A	0.96
C8—C9	1.542 (3)	C22—H22B	0.96
C8—H8	0.98	C22—H22C	0.96
C9—C11	1.526 (3)	C23—H23A	0.96
C9—C10	1.547 (3)	C23—H23B	0.96
C9—H9	0.98	C23—H23C	0.96
C10—C19	1.530 (3)	C24—H24A	0.96
C11—C12	1.523 (4)	C24—H24B	0.96
C11—H11A	0.97	C24—H24C	0.96
C11—H11B	0.97
C24—N1—C3	114.2 (2)	C11—C12—H12B	109.2
C24—N1—H1	111 (3)	C13—C12—H12B	109.2
C3—N1—H1	106 (2)	H12A—C12—H12B	107.9
C23—N2—C22	112.1 (3)	C12—C13—C18	110.56 (18)
C23—N2—C20	112.9 (3)	C12—C13—C14	106.6 (2)
C22—N2—C20	114.0 (3)	C18—C13—C14	112.4 (2)
C2—C1—C10	113.6 (2)	C12—C13—C17	116.8 (2)
C2—C1—H1A	108.8	C18—C13—C17	110.2 (2)
C10—C1—H1A	108.8	C14—C13—C17	99.87 (16)
C2—C1—H1B	108.8	C8—C14—C15	118.6 (2)
C10—C1—H1B	108.8	C8—C14—C13	114.68 (16)
H1A—C1—H1B	107.7	C15—C14—C13	104.1 (2)
C3—C2—C1	112.85 (19)	C8—C14—H14	106.2
C3—C2—H2A	109.0	C15—C14—H14	106.2
C1—C2—H2A	109.0	C13—C14—H14	106.2
C3—C2—H2B	109.0	C14—C15—C16	103.8 (2)
C1—C2—H2B	109.0	C14—C15—H15A	111.0
H2A—C2—H2B	107.8	C16—C15—H15A	111.0
N1—C3—C4	110.6 (2)	C14—C15—H15B	111.0
N1—C3—C2	110.58 (19)	C16—C15—H15B	111.0
C4—C3—C2	110.7 (2)	H15A—C15—H15B	109.0
N1—C3—H3	108.3	C15—C16—C17	107.2 (2)
C4—C3—H3	108.3	C15—C16—H16A	110.3
C2—C3—H3	108.3	C17—C16—H16A	110.3
C3—C4—C5	112.3 (2)	C15—C16—H16B	110.3
C3—C4—H4A	109.2	C17—C16—H16B	110.3
C5—C4—H4A	109.2	H16A—C16—H16B	108.5
C3—C4—H4B	109.2	C20—C17—C16	111.2 (2)
C5—C4—H4B	109.2	C20—C17—C13	119.92 (19)
H4A—C4—H4B	107.9	C16—C17—C13	103.30 (19)
C6—C5—C4	111.6 (2)	C20—C17—H17	107.3
C6—C5—C10	112.3 (2)	C16—C17—H17	107.3
C4—C5—C10	113.16 (18)	C13—C17—H17	107.3
C6—C5—H5	106.4	C13—C18—H18A	109.5
C4—C5—H5	106.4	C13—C18—H18B	109.5
C10—C5—H5	106.4	H18A—C18—H18B	109.5
C7—C6—C5	111.5 (2)	C13—C18—H18C	109.5
C7—C6—H6A	109.3	H18A—C18—H18C	109.5
C5—C6—H6A	109.3	H18B—C18—H18C	109.5
C7—C6—H6B	109.3	C10—C19—H19A	109.5
C5—C6—H6B	109.3	C10—C19—H19B	109.5
H6A—C6—H6B	108.0	H19A—C19—H19B	109.5
C8—C7—C6	111.9 (2)	C10—C19—H19C	109.5
C8—C7—H7A	109.2	H19A—C19—H19C	109.5
C6—C7—H7A	109.2	H19B—C19—H19C	109.5
C8—C7—H7B	109.2	N2—C20—C21	113.9 (2)
C6—C7—H7B	109.2	N2—C20—C17	109.7 (2)
H7A—C7—H7B	107.9	C21—C20—C17	113.1 (3)
C14—C8—C7	111.39 (17)	N2—C20—H20	106.5
C14—C8—C9	109.23 (19)	C21—C20—H20	106.5
C7—C8—C9	111.0 (2)	C17—C20—H20	106.5
C14—C8—H8	108.4	C20—C21—H21A	109.5
C7—C8—H8	108.4	C20—C21—H21B	109.5
C9—C8—H8	108.4	H21A—C21—H21B	109.5
C11—C9—C8	111.0 (2)	C20—C21—H21C	109.5
C11—C9—C10	114.63 (17)	H21A—C21—H21C	109.5
C8—C9—C10	111.74 (18)	H21B—C21—H21C	109.5
C11—C9—H9	106.3	N2—C22—H22A	109.5
C8—C9—H9	106.3	N2—C22—H22B	109.5
C10—C9—H9	106.3	H22A—C22—H22B	109.5
C19—C10—C1	108.78 (18)	N2—C22—H22C	109.5
C19—C10—C5	112.3 (2)	H22A—C22—H22C	109.5
C1—C10—C5	106.4 (2)	H22B—C22—H22C	109.5
C19—C10—C9	110.3 (2)	N2—C23—H23A	109.5
C1—C10—C9	111.27 (19)	N2—C23—H23B	109.5
C5—C10—C9	107.72 (16)	H23A—C23—H23B	109.5
C12—C11—C9	114.19 (18)	N2—C23—H23C	109.5
C12—C11—H11A	108.7	H23A—C23—H23C	109.5
C9—C11—H11A	108.7	H23B—C23—H23C	109.5
C12—C11—H11B	108.7	N1—C24—H24A	109.5
C9—C11—H11B	108.7	N1—C24—H24B	109.5
H11A—C11—H11B	107.6	H24A—C24—H24B	109.5
C11—C12—C13	112.0 (2)	N1—C24—H24C	109.5
C11—C12—H12A	109.2	H24A—C24—H24C	109.5
C13—C12—H12A	109.2	H24B—C24—H24C	109.5
C10—C1—C2—C3	−55.5 (3)	C10—C9—C11—C12	178.6 (2)
C24—N1—C3—C4	−66.4 (4)	C9—C11—C12—C13	−54.4 (3)
C24—N1—C3—C2	170.6 (3)	C11—C12—C13—C18	−66.8 (3)
C1—C2—C3—N1	174.9 (2)	C11—C12—C13—C14	55.6 (2)
C1—C2—C3—C4	52.0 (3)	C11—C12—C13—C17	166.1 (2)
N1—C3—C4—C5	−175.6 (2)	C7—C8—C14—C15	−54.5 (3)
C2—C3—C4—C5	−52.7 (3)	C9—C8—C14—C15	−177.5 (2)
C3—C4—C5—C6	−175.1 (2)	C7—C8—C14—C13	−178.2 (2)
C3—C4—C5—C10	57.1 (3)	C9—C8—C14—C13	58.7 (3)
C4—C5—C6—C7	174.9 (3)	C12—C13—C14—C8	−60.3 (3)
C10—C5—C6—C7	−56.8 (3)	C18—C13—C14—C8	60.9 (3)
C5—C6—C7—C8	54.0 (4)	C17—C13—C14—C8	177.8 (2)
C6—C7—C8—C14	−175.7 (3)	C12—C13—C14—C15	168.5 (2)
C6—C7—C8—C9	−53.7 (3)	C18—C13—C14—C15	−70.2 (2)
C14—C8—C9—C11	−51.0 (2)	C17—C13—C14—C15	46.6 (2)
C7—C8—C9—C11	−174.2 (2)	C8—C14—C15—C16	−163.6 (2)
C14—C8—C9—C10	179.63 (19)	C13—C14—C15—C16	−34.7 (3)
C7—C8—C9—C10	56.4 (2)	C14—C15—C16—C17	8.9 (3)
C2—C1—C10—C19	−66.2 (3)	C15—C16—C17—C20	149.6 (3)
C2—C1—C10—C5	55.0 (2)	C15—C16—C17—C13	19.7 (3)
C2—C1—C10—C9	172.0 (2)	C12—C13—C17—C20	81.4 (3)
C6—C5—C10—C19	−64.3 (3)	C18—C13—C17—C20	−45.8 (3)
C4—C5—C10—C19	63.2 (3)	C14—C13—C17—C20	−164.3 (2)
C6—C5—C10—C1	176.8 (2)	C12—C13—C17—C16	−154.2 (2)
C4—C5—C10—C1	−55.7 (3)	C18—C13—C17—C16	78.5 (3)
C6—C5—C10—C9	57.4 (3)	C14—C13—C17—C16	−39.9 (2)
C4—C5—C10—C9	−175.1 (2)	C23—N2—C20—C21	74.6 (4)
C11—C9—C10—C19	−61.6 (3)	C22—N2—C20—C21	−54.8 (4)
C8—C9—C10—C19	65.8 (2)	C23—N2—C20—C17	−157.6 (3)
C11—C9—C10—C1	59.3 (3)	C22—N2—C20—C17	73.1 (3)
C8—C9—C10—C1	−173.31 (19)	C16—C17—C20—N2	50.2 (3)
C11—C9—C10—C5	175.5 (2)	C13—C17—C20—N2	170.7 (2)
C8—C9—C10—C5	−57.1 (2)	C16—C17—C20—C21	178.5 (2)
C8—C9—C11—C12	50.9 (3)	C13—C17—C20—C21	−61.0 (3)