3α,20-Bis(dimethyl­amino)-4,4,14-trimethyl-9,19-cyclo-5α-pregnan-16-ol

The title compound, C₂₈H₅₀N₂O, also known as cyclo­virobuxine A, was obtained from N-methyl­ation of naturally occurring cyclo­virobuxine D. It has a four-ring triterpenoid nucleus in a trans–cis–trans configuration. The six-membered rings have chair conformations, while the conformation of the five-membered ring is an envelope.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.054
• wR factor = 0.095
• Data-to-parameter ratio = 7.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         45 Perc.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.94
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8

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           25.01
           From the CIF: _reflns_number_total               2224
           Count of symmetry unique reflns         2249
           Completeness (_total/calc)             98.89%
           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
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C25    = .          S

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

   9 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

3α,20-Bis(dimethylamino)-4,4,14-trimethyl-9,19-cyclo-5α-pregnan-16-ol

Crystal data

C28H50N2O	Z = 1
Mr = 430.70	F(000) = 240
Triclinic, P1	Dx = 1.125 Mg m^−3
Hall symbol: P 1	Melting point = 514–515 K
a = 6.245 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.106 (4) Å	Cell parameters from 514 reflections
c = 15.858 (8) Å	θ = 2.6–18.9°
α = 77.993 (9)°	µ = 0.07 mm^−1
β = 87.575 (10)°	T = 294 K
γ = 67.574 (8)°	Plate, colorless
V = 635.7 (6) Å^3	0.45 × 0.38 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2224 independent reflections
Radiation source: fine-focus sealed tube	1002 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
φ and ω scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SABABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.971, Tmax = 0.993	k = −7→8
3380 measured reflections	l = −9→18

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.095	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0225P)^2] where P = (Fo^2 + 2Fc^2)/3
2224 reflections	(Δ/σ)max < 0.001
280 parameters	Δρmax = 0.16 e Å^−3
3 restraints	Δρmin = −0.16 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	0.8098 (9)	0.2534 (8)	0.9081 (3)	0.0663 (16)
N2	0.3152 (9)	0.6844 (8)	0.1053 (3)	0.0659 (15)
O1	0.5083 (7)	0.2560 (6)	0.1959 (3)	0.0852 (15)
H1	0.4539	0.3307	0.1489	0.128*
C1	0.7162 (9)	0.2899 (8)	0.8199 (4)	0.0528 (17)
H1C	0.5858	0.2442	0.8271	0.063*
C2	0.8885 (10)	0.1462 (8)	0.7640 (4)	0.0543 (17)
C3	0.7672 (9)	0.1855 (8)	0.6756 (4)	0.0448 (15)
H3	0.6357	0.1428	0.6889	0.054*
C4	0.9107 (10)	0.0479 (8)	0.6147 (4)	0.0581 (18)
H4A	1.0468	0.0799	0.5991	0.070*
H4B	0.9621	−0.0973	0.6436	0.070*
C5	0.7675 (10)	0.0846 (8)	0.5351 (4)	0.0568 (18)
H5A	0.6237	0.0674	0.5517	0.068*
H5B	0.8505	−0.0188	0.5016	0.068*
C6	0.7123 (10)	0.2996 (8)	0.4796 (4)	0.0491 (16)
H6	0.8618	0.3040	0.4601	0.059*
C7	0.5654 (9)	0.3453 (8)	0.3973 (3)	0.0419 (16)
C8	0.7019 (10)	0.2205 (8)	0.3303 (4)	0.0562 (17)
H8A	0.8660	0.1916	0.3360	0.067*
H8B	0.6809	0.0898	0.3373	0.067*
C9	0.5988 (10)	0.3624 (9)	0.2425 (4)	0.0593 (18)
H9	0.7213	0.3950	0.2098	0.071*
C10	0.4139 (9)	0.5635 (8)	0.2607 (4)	0.0478 (16)
H10	0.2689	0.5402	0.2694	0.057*
C11	0.4977 (9)	0.5743 (8)	0.3494 (4)	0.0443 (16)
C12	0.3214 (9)	0.7124 (8)	0.4028 (4)	0.0549 (17)
H12A	0.1714	0.7069	0.3939	0.066*
H12B	0.3073	0.8552	0.3819	0.066*
C13	0.3840 (9)	0.6510 (8)	0.4995 (4)	0.0558 (17)
H13A	0.2594	0.6176	0.5287	0.067*
H13B	0.3843	0.7733	0.5174	0.067*
C14	0.6122 (10)	0.4710 (8)	0.5335 (4)	0.0484 (17)
C15	0.6597 (9)	0.4107 (9)	0.6303 (4)	0.0435 (15)
C16	0.4917 (9)	0.5411 (8)	0.6872 (4)	0.0545 (17)
H16A	0.4323	0.6863	0.6579	0.065*
H16B	0.3617	0.4977	0.6979	0.065*
C17	0.6109 (10)	0.5171 (8)	0.7720 (4)	0.0628 (19)
H17A	0.4996	0.5983	0.8081	0.075*
H17B	0.7325	0.5716	0.7612	0.075*
C18	0.7964 (10)	0.5194 (8)	0.5739 (4)	0.0567 (17)
H18A	0.9575	0.4380	0.5655	0.068*
H18B	0.7629	0.6634	0.5757	0.068*
C19	0.6360 (12)	0.2449 (11)	0.9717 (4)	0.102 (3)
H19A	0.7012	0.2209	1.0285	0.154*
H19B	0.5881	0.1337	0.9676	0.154*
H19C	0.5044	0.3744	0.9607	0.154*
C20	0.9075 (11)	0.4010 (10)	0.9226 (4)	0.097 (2)
H20A	0.9639	0.3656	0.9815	0.145*
H20B	0.7899	0.5389	0.9109	0.145*
H20C	1.0331	0.3956	0.8848	0.145*
C21	0.9399 (11)	−0.0790 (9)	0.8126 (4)	0.076 (2)
H21A	1.0474	−0.1741	0.7812	0.115*
H21B	0.7985	−0.1034	0.8179	0.115*
H21C	1.0059	−0.0998	0.8690	0.115*
C22	1.1168 (9)	0.1819 (10)	0.7554 (4)	0.078 (2)
H22A	1.0863	0.3228	0.7262	0.117*
H22B	1.2217	0.0880	0.7230	0.117*
H22C	1.1849	0.1574	0.8118	0.117*
C23	0.3526 (9)	0.2877 (8)	0.4191 (4)	0.0618 (18)
H23A	0.2637	0.3640	0.4605	0.093*
H23B	0.4030	0.1412	0.4427	0.093*
H23C	0.2584	0.3221	0.3675	0.093*
C24	0.7069 (9)	0.6384 (8)	0.3386 (4)	0.0587 (17)
H24A	0.8192	0.5534	0.3049	0.088*
H24B	0.7754	0.6200	0.3943	0.088*
H24C	0.6574	0.7819	0.3098	0.088*
C25	0.3699 (10)	0.7467 (9)	0.1831 (4)	0.0607 (18)
H25	0.5170	0.7658	0.1733	0.073*
C26	0.1912 (9)	0.9531 (8)	0.1986 (4)	0.075 (2)
H26A	0.1742	1.0604	0.1483	0.112*
H26B	0.2423	0.9886	0.2472	0.112*
H26C	0.0448	0.9400	0.2101	0.112*
C27	0.3656 (13)	0.8050 (10)	0.0265 (4)	0.097 (3)
H27A	0.5220	0.7967	0.0305	0.146*
H27B	0.2605	0.9476	0.0189	0.146*
H27C	0.3475	0.7499	−0.0220	0.146*
C28	0.0785 (12)	0.6953 (11)	0.0997 (4)	0.089 (2)
H28A	0.0461	0.6162	0.1519	0.133*
H28B	0.0608	0.6390	0.0516	0.133*
H28C	−0.0274	0.8377	0.0919	0.133*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.081 (4)	0.060 (4)	0.051 (4)	−0.019 (3)	−0.008 (3)	−0.009 (3)
N2	0.076 (4)	0.067 (4)	0.056 (4)	−0.028 (3)	−0.009 (3)	−0.010 (3)
O1	0.113 (4)	0.063 (3)	0.081 (3)	−0.024 (3)	−0.016 (3)	−0.034 (2)
C1	0.052 (4)	0.041 (4)	0.068 (5)	−0.020 (3)	0.004 (4)	−0.013 (4)
C2	0.045 (4)	0.037 (4)	0.078 (5)	−0.010 (3)	−0.006 (4)	−0.015 (4)
C3	0.033 (3)	0.035 (4)	0.062 (4)	−0.010 (3)	0.001 (3)	−0.009 (3)
C4	0.056 (4)	0.031 (4)	0.075 (5)	−0.006 (3)	0.003 (4)	−0.006 (3)
C5	0.061 (4)	0.035 (4)	0.066 (5)	−0.005 (3)	−0.001 (4)	−0.019 (3)
C6	0.050 (4)	0.033 (4)	0.064 (5)	−0.013 (3)	0.013 (3)	−0.019 (3)
C7	0.041 (4)	0.032 (4)	0.056 (5)	−0.013 (3)	0.004 (3)	−0.019 (3)
C8	0.064 (4)	0.039 (4)	0.067 (4)	−0.016 (3)	0.008 (4)	−0.022 (3)
C9	0.065 (5)	0.050 (4)	0.071 (5)	−0.027 (4)	0.015 (4)	−0.021 (4)
C10	0.038 (4)	0.040 (4)	0.070 (5)	−0.014 (3)	0.006 (3)	−0.023 (3)
C11	0.040 (4)	0.039 (4)	0.055 (5)	−0.014 (3)	0.004 (3)	−0.015 (3)
C12	0.055 (4)	0.046 (4)	0.062 (5)	−0.013 (3)	0.000 (4)	−0.020 (3)
C13	0.057 (4)	0.041 (4)	0.061 (5)	−0.006 (4)	0.006 (3)	−0.017 (3)
C14	0.046 (4)	0.028 (3)	0.067 (5)	−0.008 (3)	0.001 (4)	−0.013 (3)
C15	0.036 (3)	0.040 (4)	0.052 (4)	−0.009 (3)	0.009 (3)	−0.013 (3)
C16	0.051 (4)	0.041 (4)	0.060 (5)	−0.006 (3)	0.001 (4)	−0.010 (3)
C17	0.066 (5)	0.042 (4)	0.065 (5)	−0.002 (4)	−0.001 (4)	−0.014 (4)
C18	0.058 (4)	0.041 (4)	0.078 (5)	−0.025 (3)	0.015 (3)	−0.018 (3)
C19	0.129 (7)	0.099 (6)	0.065 (6)	−0.037 (6)	0.022 (5)	−0.004 (5)
C20	0.119 (7)	0.092 (6)	0.087 (6)	−0.038 (5)	−0.026 (5)	−0.031 (4)
C21	0.089 (5)	0.041 (4)	0.085 (6)	−0.010 (4)	−0.005 (4)	−0.010 (4)
C22	0.049 (4)	0.083 (5)	0.103 (6)	−0.021 (4)	−0.001 (4)	−0.030 (4)
C23	0.061 (4)	0.050 (4)	0.078 (5)	−0.027 (3)	0.011 (3)	−0.012 (3)
C24	0.054 (4)	0.048 (4)	0.078 (5)	−0.025 (3)	0.001 (3)	−0.010 (3)
C25	0.060 (4)	0.053 (4)	0.067 (5)	−0.019 (4)	−0.007 (4)	−0.012 (4)
C26	0.075 (5)	0.062 (5)	0.073 (5)	−0.007 (4)	−0.001 (4)	−0.018 (4)
C27	0.127 (7)	0.080 (6)	0.068 (5)	−0.027 (5)	0.011 (5)	−0.008 (4)
C28	0.094 (6)	0.098 (6)	0.087 (6)	−0.046 (5)	−0.019 (5)	−0.022 (4)

Geometric parameters (Å, º)

N1—C20	1.457 (7)	C13—H13A	0.9700
N1—C19	1.459 (7)	C13—H13B	0.9700
N1—C1	1.473 (7)	C14—C15	1.515 (7)
N2—C28	1.456 (7)	C14—C18	1.519 (7)
N2—C27	1.457 (7)	C15—C18	1.509 (7)
N2—C25	1.488 (7)	C15—C16	1.517 (7)
O1—C9	1.425 (6)	C16—C17	1.511 (7)
O1—H1	0.8200	C16—H16A	0.9700
C1—C17	1.529 (7)	C16—H16B	0.9700
C1—C2	1.563 (7)	C17—H17A	0.9700
C1—H1C	0.9800	C17—H17B	0.9700
C2—C22	1.537 (7)	C18—H18A	0.9700
C2—C21	1.541 (7)	C18—H18B	0.9700
C2—C3	1.543 (7)	C19—H19A	0.9600
C3—C15	1.506 (6)	C19—H19B	0.9600
C3—C4	1.531 (7)	C19—H19C	0.9600
C3—H3	0.9800	C20—H20A	0.9600
C4—C5	1.497 (7)	C20—H20B	0.9600
C4—H4A	0.9700	C20—H20C	0.9600
C4—H4B	0.9700	C21—H21A	0.9600
C5—C6	1.514 (7)	C21—H21B	0.9600
C5—H5A	0.9700	C21—H21C	0.9600
C5—H5B	0.9700	C22—H22A	0.9600
C6—C7	1.532 (6)	C22—H22B	0.9600
C6—C14	1.553 (7)	C22—H22C	0.9600
C6—H6	0.9800	C23—H23A	0.9600
C7—C23	1.539 (7)	C23—H23B	0.9600
C7—C8	1.543 (7)	C23—H23C	0.9600
C7—C11	1.547 (7)	C24—H24A	0.9600
C8—C9	1.538 (7)	C24—H24B	0.9600
C8—H8A	0.9700	C24—H24C	0.9600
C8—H8B	0.9700	C25—C26	1.528 (7)
C9—C10	1.530 (7)	C25—H25	0.9800
C9—H9	0.9800	C26—H26A	0.9600
C10—C25	1.540 (7)	C26—H26B	0.9600
C10—C11	1.549 (7)	C26—H26C	0.9600
C10—H10	0.9800	C27—H27A	0.9600
C11—C12	1.528 (7)	C27—H27B	0.9600
C11—C24	1.531 (7)	C27—H27C	0.9600
C12—C13	1.528 (7)	C28—H28A	0.9600
C12—H12A	0.9700	C28—H28B	0.9600
C12—H12B	0.9700	C28—H28C	0.9600
C13—C14	1.531 (6)
C20—N1—C19	109.5 (6)	C15—C14—C6	118.6 (4)
C20—N1—C1	115.2 (5)	C18—C14—C6	113.7 (5)
C19—N1—C1	111.1 (5)	C13—C14—C6	116.8 (5)
C28—N2—C27	109.9 (5)	C3—C15—C18	122.3 (5)
C28—N2—C25	114.2 (5)	C3—C15—C14	121.0 (5)
C27—N2—C25	111.3 (5)	C18—C15—C14	60.3 (4)
C9—O1—H1	109.5	C3—C15—C16	111.3 (5)
N1—C1—C17	116.0 (5)	C18—C15—C16	114.5 (5)
N1—C1—C2	112.7 (5)	C14—C15—C16	118.9 (5)
C17—C1—C2	112.4 (5)	C17—C16—C15	110.5 (5)
N1—C1—H1C	104.8	C17—C16—H16A	109.6
C17—C1—H1C	104.8	C15—C16—H16A	109.6
C2—C1—H1C	104.8	C17—C16—H16B	109.6
C22—C2—C21	108.8 (5)	C15—C16—H16B	109.6
C22—C2—C3	112.4 (5)	H16A—C16—H16B	108.1
C21—C2—C3	109.9 (5)	C16—C17—C1	112.0 (5)
C22—C2—C1	111.1 (5)	C16—C17—H17A	109.2
C21—C2—C1	106.1 (5)	C1—C17—H17A	109.2
C3—C2—C1	108.4 (5)	C16—C17—H17B	109.2
C15—C3—C4	111.6 (5)	C1—C17—H17B	109.2
C15—C3—C2	115.0 (5)	H17A—C17—H17B	107.9
C4—C3—C2	114.7 (4)	C15—C18—C14	60.1 (4)
C15—C3—H3	104.7	C15—C18—H18A	117.8
C4—C3—H3	104.7	C14—C18—H18A	117.8
C2—C3—H3	104.7	C15—C18—H18B	117.8
C5—C4—C3	109.9 (5)	C14—C18—H18B	117.8
C5—C4—H4A	109.7	H18A—C18—H18B	114.9
C3—C4—H4A	109.7	N1—C19—H19A	109.5
C5—C4—H4B	109.7	N1—C19—H19B	109.5
C3—C4—H4B	109.7	H19A—C19—H19B	109.5
H4A—C4—H4B	108.2	N1—C19—H19C	109.5
C4—C5—C6	112.4 (5)	H19A—C19—H19C	109.5
C4—C5—H5A	109.1	H19B—C19—H19C	109.5
C6—C5—H5A	109.1	N1—C20—H20A	109.5
C4—C5—H5B	109.1	N1—C20—H20B	109.5
C6—C5—H5B	109.1	H20A—C20—H20B	109.5
H5A—C5—H5B	107.8	N1—C20—H20C	109.5
C5—C6—C7	114.5 (5)	H20A—C20—H20C	109.5
C5—C6—C14	111.4 (5)	H20B—C20—H20C	109.5
C7—C6—C14	112.8 (4)	C2—C21—H21A	109.5
C5—C6—H6	105.8	C2—C21—H21B	109.5
C7—C6—H6	105.8	H21A—C21—H21B	109.5
C14—C6—H6	105.8	C2—C21—H21C	109.5
C6—C7—C23	110.1 (4)	H21A—C21—H21C	109.5
C6—C7—C8	112.3 (4)	H21B—C21—H21C	109.5
C23—C7—C8	107.7 (5)	C2—C22—H22A	109.5
C6—C7—C11	110.9 (4)	C2—C22—H22B	109.5
C23—C7—C11	112.4 (4)	H22A—C22—H22B	109.5
C8—C7—C11	103.4 (4)	C2—C22—H22C	109.5
C9—C8—C7	104.5 (4)	H22A—C22—H22C	109.5
C9—C8—H8A	110.8	H22B—C22—H22C	109.5
C7—C8—H8A	110.8	C7—C23—H23A	109.5
C9—C8—H8B	110.8	C7—C23—H23B	109.5
C7—C8—H8B	110.8	H23A—C23—H23B	109.5
H8A—C8—H8B	108.9	C7—C23—H23C	109.5
O1—C9—C10	113.0 (5)	H23A—C23—H23C	109.5
O1—C9—C8	109.0 (5)	H23B—C23—H23C	109.5
C10—C9—C8	107.2 (5)	C11—C24—H24A	109.5
O1—C9—H9	109.2	C11—C24—H24B	109.5
C10—C9—H9	109.2	H24A—C24—H24B	109.5
C8—C9—H9	109.2	C11—C24—H24C	109.5
C9—C10—C25	111.7 (5)	H24A—C24—H24C	109.5
C9—C10—C11	102.7 (4)	H24B—C24—H24C	109.5
C25—C10—C11	120.3 (4)	N2—C25—C26	113.8 (5)
C9—C10—H10	107.1	N2—C25—C10	108.4 (5)
C25—C10—H10	107.1	C26—C25—C10	113.9 (5)
C11—C10—H10	107.1	N2—C25—H25	106.8
C12—C11—C24	108.4 (5)	C26—C25—H25	106.8
C12—C11—C7	108.0 (5)	C10—C25—H25	106.8
C24—C11—C7	112.0 (4)	C25—C26—H26A	109.5
C12—C11—C10	117.9 (4)	C25—C26—H26B	109.5
C24—C11—C10	110.0 (5)	H26A—C26—H26B	109.5
C7—C11—C10	100.3 (4)	C25—C26—H26C	109.5
C11—C12—C13	113.9 (4)	H26A—C26—H26C	109.5
C11—C12—H12A	108.8	H26B—C26—H26C	109.5
C13—C12—H12A	108.8	N2—C27—H27A	109.5
C11—C12—H12B	108.8	N2—C27—H27B	109.5
C13—C12—H12B	108.8	H27A—C27—H27B	109.5
H12A—C12—H12B	107.7	N2—C27—H27C	109.5
C12—C13—C14	119.7 (5)	H27A—C27—H27C	109.5
C12—C13—H13A	107.4	H27B—C27—H27C	109.5
C14—C13—H13A	107.4	N2—C28—H28A	109.5
C12—C13—H13B	107.4	N2—C28—H28B	109.5
C14—C13—H13B	107.4	H28A—C28—H28B	109.5
H13A—C13—H13B	106.9	N2—C28—H28C	109.5
C15—C14—C18	59.6 (4)	H28A—C28—H28C	109.5
C15—C14—C13	117.3 (5)	H28B—C28—H28C	109.5
C18—C14—C13	118.3 (5)
C20—N1—C1—C17	−32.3 (8)	C25—C10—C11—C24	−50.2 (6)
C19—N1—C1—C17	92.9 (6)	C9—C10—C11—C7	−43.6 (5)
C20—N1—C1—C2	99.2 (6)	C25—C10—C11—C7	−168.4 (5)
C19—N1—C1—C2	−135.5 (5)	C24—C11—C12—C13	−77.5 (6)
N1—C1—C2—C22	−60.1 (6)	C7—C11—C12—C13	44.1 (6)
C17—C1—C2—C22	73.2 (6)	C10—C11—C12—C13	156.8 (5)
N1—C1—C2—C21	58.0 (6)	C11—C12—C13—C14	2.6 (7)
C17—C1—C2—C21	−168.7 (5)	C12—C13—C14—C15	−177.2 (5)
N1—C1—C2—C3	175.9 (4)	C12—C13—C14—C18	114.4 (6)
C17—C1—C2—C3	−50.7 (6)	C12—C13—C14—C6	−27.3 (7)
C22—C2—C3—C15	−71.9 (6)	C5—C6—C14—C15	21.2 (7)
C21—C2—C3—C15	166.9 (5)	C7—C6—C14—C15	151.6 (5)
C1—C2—C3—C15	51.3 (6)	C5—C6—C14—C18	88.3 (6)
C22—C2—C3—C4	59.6 (6)	C7—C6—C14—C18	−141.3 (5)
C21—C2—C3—C4	−61.7 (6)	C5—C6—C14—C13	−128.3 (5)
C1—C2—C3—C4	−177.2 (5)	C7—C6—C14—C13	2.1 (7)
C15—C3—C4—C5	−52.6 (6)	C4—C3—C15—C18	−47.3 (7)
C2—C3—C4—C5	174.3 (5)	C2—C3—C15—C18	85.7 (7)
C3—C4—C5—C6	68.2 (6)	C4—C3—C15—C14	25.1 (7)
C4—C5—C6—C7	−179.8 (4)	C2—C3—C15—C14	158.0 (5)
C4—C5—C6—C14	−50.3 (7)	C4—C3—C15—C16	172.1 (5)
C5—C6—C7—C23	49.5 (6)	C2—C3—C15—C16	−55.0 (6)
C14—C6—C7—C23	−79.4 (6)	C18—C14—C15—C3	−112.1 (6)
C5—C6—C7—C8	−70.5 (6)	C13—C14—C15—C3	139.5 (5)
C14—C6—C7—C8	160.7 (5)	C6—C14—C15—C3	−9.9 (8)
C5—C6—C7—C11	174.5 (5)	C13—C14—C15—C18	−108.5 (5)
C14—C6—C7—C11	45.7 (6)	C6—C14—C15—C18	102.2 (6)
C6—C7—C8—C9	−148.5 (4)	C18—C14—C15—C16	103.3 (6)
C23—C7—C8—C9	90.2 (5)	C13—C14—C15—C16	−5.1 (7)
C11—C7—C8—C9	−28.9 (6)	C6—C14—C15—C16	−154.5 (5)
C7—C8—C9—O1	−121.2 (5)	C3—C15—C16—C17	55.8 (6)
C7—C8—C9—C10	1.4 (6)	C18—C15—C16—C17	−88.1 (6)
O1—C9—C10—C25	−83.1 (6)	C14—C15—C16—C17	−156.4 (5)
C8—C9—C10—C25	156.7 (5)	C15—C16—C17—C1	−57.2 (7)
O1—C9—C10—C11	146.6 (5)	N1—C1—C17—C16	−172.4 (5)
C8—C9—C10—C11	26.5 (6)	C2—C1—C17—C16	55.9 (7)
C6—C7—C11—C12	−70.5 (5)	C3—C15—C18—C14	109.9 (6)
C23—C7—C11—C12	53.2 (6)	C16—C15—C18—C14	−110.6 (5)
C8—C7—C11—C12	169.0 (5)	C13—C14—C18—C15	106.7 (6)
C6—C7—C11—C24	48.8 (6)	C6—C14—C18—C15	−110.4 (5)
C23—C7—C11—C24	172.5 (5)	C28—N2—C25—C26	−49.2 (7)
C8—C7—C11—C24	−71.7 (6)	C27—N2—C25—C26	76.0 (7)
C6—C7—C11—C10	165.4 (4)	C28—N2—C25—C10	78.6 (6)
C23—C7—C11—C10	−70.9 (5)	C27—N2—C25—C10	−156.3 (5)
C8—C7—C11—C10	45.0 (5)	C9—C10—C25—N2	53.8 (6)
C9—C10—C11—C12	−160.5 (5)	C11—C10—C25—N2	174.3 (5)
C25—C10—C11—C12	74.7 (7)	C9—C10—C25—C26	−178.4 (5)
C9—C10—C11—C24	74.6 (5)	C11—C10—C25—C26	−58.0 (7)