4,4,14-Tri­methyl-3α,20-bis­(methyl­amino)-9,19-cyclo-5α-pregnan-16-ol

The title compound, C₂₆H₄₆N₂O, also known as cyclo­virobuxine D, has for the first time been isolated from Buxus papilosa. It has a steroid nucleus in trans/cis/trans configuration. Two of the three cyclo­hexane rings adopt half-chair conformations and the third ring, with an equatorially attached methyl­amino substituent, is in a chair conformation. The cyclo­pentane ring has a half-chair conformation and the N-methyl­amino­ethane group is equatorially attached to it. N—H...O and C—H...N interactions are observed in the molecular structure and the crystal structure is stabilized by van der Waals interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.064
• wR factor = 0.192
• Data-to-parameter ratio = 8.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor       O1     -   H1O    ...          ?

Alert level C
PLAT024_ALERT_4_C Merging of Friedel Data Preferred for Z<=Si ....          !
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         C4
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1N    ...          ?

Alert level G
REFLT03_ALERT_4_G  ALERT: MoKa measured Friedel data cannot be used to
                   determine absolute structure in a light-atom
                   study EXCEPT under VERY special conditions.
                   It is preferred that Friedel data is merged in such cases.
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _reflns_number_total               4093
           Count of symmetry unique reflns         2336
           Completeness (_total/calc)            175.21%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1757
           Fraction of Friedel pairs measured     0.752
           Are heavy atom types Z>Si present           no

   0 ALERT level A = In general: serious problem
   1 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
   2 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, 1990).

4,4,14-Trimethyl-3α,20-bis(methylamino)-9,19-cyclo-5α-pregnan-16-ol

Crystal data

C26H46N2O	F(000) = 448
Mr = 402.65	Dx = 1.096 Mg m^−3
Monoclinic, P21	Melting point: 478-483 K K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 13.410 (3) Å	Cell parameters from 8359 reflections
b = 6.7225 (13) Å	θ = 1.5–25.0°
c = 13.946 (3) Å	µ = 0.07 mm^−1
β = 104.032 (4)°	T = 293 K
V = 1219.6 (4) Å^3	Plate, colourless
Z = 2	0.58 × 0.27 × 0.19 mm

Data collection

Siemens SMART CCD area-detector diffractometer	4093 independent reflections
Radiation source: fine-focus sealed tube	2925 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 8.33 pixels mm^-1	θmax = 25.0°, θmin = 1.5°
ω scans	h = −14→15
Absorption correction: multi-scan (SABABS; Sheldrick, 1996)	k = −7→7
Tmin = 0.963, Tmax = 0.988	l = −16→16
6796 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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.192	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + 0.1417P] where P = (Fo^2 + 2Fc^2)/3
2333 reflections	(Δ/σ)max = 0.001
263 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.15 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	0.1306 (4)	0.6352 (8)	0.4965 (4)	0.1131 (15)
H1N	0.0934	0.6081	0.5407	0.136*
N2	0.9700 (3)	0.4485 (8)	1.1314 (3)	0.0936 (12)
H2N	0.9957	0.3792	1.0869	0.112*
O1	0.9581 (2)	0.3189 (7)	0.9244 (3)	0.1019 (11)
H1O	0.9593	0.4321	0.9027	0.153*
C1	0.3660 (4)	0.7670 (8)	0.7026 (4)	0.0885 (13)
H1A	0.3983	0.8574	0.6651	0.106*
H1B	0.3720	0.8241	0.7676	0.106*
C2	0.2545 (4)	0.7430 (8)	0.6514 (4)	0.0946 (14)
H2A	0.2218	0.8726	0.6442	0.113*
H2B	0.2214	0.6618	0.6922	0.113*
C3	0.2389 (4)	0.6475 (8)	0.5504 (4)	0.0906 (14)
H3	0.2726	0.7347	0.5115	0.109*
C4	0.2926 (4)	0.4462 (8)	0.5557 (3)	0.0851 (13)
C5	0.4068 (3)	0.4753 (7)	0.6101 (3)	0.0764 (11)
H5	0.4325	0.5757	0.5711	0.092*
C6	0.4759 (4)	0.2979 (10)	0.6113 (4)	0.0973 (15)
H6A	0.4727	0.2563	0.5440	0.117*
H6B	0.4524	0.1882	0.6454	0.117*
C7	0.5855 (4)	0.3489 (10)	0.6627 (4)	0.0982 (16)
H7A	0.6058	0.4690	0.6339	0.118*
H7B	0.6305	0.2421	0.6527	0.118*
C8	0.5971 (3)	0.3801 (6)	0.7728 (3)	0.0737 (11)
H8	0.5779	0.2536	0.7982	0.088*
C9	0.5183 (3)	0.5366 (6)	0.7918 (3)	0.0697 (11)
C10	0.4200 (3)	0.5702 (7)	0.7126 (3)	0.0708 (11)
C11	0.5633 (4)	0.7153 (7)	0.8552 (4)	0.0878 (13)
H11A	0.5092	0.7737	0.8813	0.105*
H11B	0.5831	0.8136	0.8124	0.105*
C12	0.6561 (4)	0.6770 (8)	0.9421 (4)	0.0866 (13)
H12A	0.7069	0.7800	0.9425	0.104*
H12B	0.6341	0.6881	1.0032	0.104*
C13	0.7070 (3)	0.4759 (7)	0.9400 (3)	0.0689 (11)
C14	0.7058 (3)	0.4231 (6)	0.8312 (3)	0.0724 (11)
C15	0.7765 (4)	0.2446 (9)	0.8441 (4)	0.0897 (14)
H15A	0.8077	0.2327	0.7885	0.108*
H15B	0.7385	0.1236	0.8487	0.108*
C16	0.8595 (3)	0.2794 (8)	0.9405 (3)	0.0833 (13)
H16	0.8635	0.1627	0.9833	0.100*
C17	0.8232 (3)	0.4600 (8)	0.9906 (3)	0.0762 (11)
H17	0.8563	0.5774	0.9705	0.091*
C18	0.6469 (4)	0.3219 (9)	0.9849 (3)	0.0900 (14)
H18A	0.5749	0.3328	0.9538	0.135*
H18B	0.6577	0.3459	1.0545	0.135*
H18C	0.6704	0.1906	0.9745	0.135*
C19	0.4184 (3)	0.4480 (9)	0.8016 (3)	0.0819 (12)
H19A	0.4096	0.3054	0.7929	0.098*
H19B	0.3863	0.5052	0.8505	0.098*
C20	0.8564 (3)	0.4502 (10)	1.1027 (3)	0.0870 (13)
H20	0.8302	0.3275	1.1255	0.104*
C21	0.8213 (4)	0.6266 (12)	1.1533 (4)	0.115 (2)
H21A	0.8565	0.6268	1.2220	0.173*
H21B	0.7486	0.6177	1.1470	0.173*
H21C	0.8366	0.7473	1.1229	0.173*
C22	0.7558 (4)	0.5897 (10)	0.7820 (4)	0.0958 (15)
H22A	0.7653	0.5435	0.7197	0.144*
H22B	0.8212	0.6245	0.8244	0.144*
H22C	0.7119	0.7045	0.7716	0.144*
C23	0.0893 (5)	0.8103 (13)	0.4440 (7)	0.153 (3)
H23A	0.0218	0.7828	0.4040	0.229*
H23B	0.1330	0.8521	0.4025	0.229*
H23C	0.0854	0.9141	0.4902	0.229*
C24	1.0121 (4)	0.3731 (12)	1.2310 (4)	0.121 (2)
H24A	1.0855	0.3620	1.2427	0.182*
H24B	0.9833	0.2446	1.2377	0.182*
H24C	0.9954	0.4631	1.2782	0.182*
C25	0.2852 (5)	0.3740 (13)	0.4504 (4)	0.125 (2)
H25A	0.2143	0.3693	0.4148	0.188*
H25B	0.3147	0.2436	0.4523	0.188*
H25C	0.3219	0.4640	0.4178	0.188*
C26	0.2390 (4)	0.2943 (9)	0.6076 (5)	0.1146 (19)
H26A	0.1668	0.2928	0.5766	0.172*
H26B	0.2491	0.3300	0.6759	0.172*
H26C	0.2674	0.1647	0.6028	0.172*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.089 (3)	0.105 (4)	0.139 (4)	−0.012 (3)	0.016 (3)	0.009 (3)
N2	0.082 (2)	0.118 (3)	0.086 (3)	0.004 (3)	0.0318 (19)	−0.005 (3)
O1	0.087 (2)	0.126 (3)	0.106 (2)	0.003 (2)	0.0475 (17)	−0.006 (2)
C1	0.093 (3)	0.072 (3)	0.096 (3)	0.009 (3)	0.015 (2)	−0.002 (2)
C2	0.099 (4)	0.076 (3)	0.107 (4)	0.009 (3)	0.021 (3)	−0.002 (3)
C3	0.087 (3)	0.078 (3)	0.105 (4)	−0.010 (3)	0.022 (3)	0.010 (3)
C4	0.097 (3)	0.073 (3)	0.089 (3)	−0.015 (3)	0.031 (2)	0.000 (3)
C5	0.086 (3)	0.069 (3)	0.079 (3)	−0.005 (2)	0.032 (2)	0.000 (2)
C6	0.100 (4)	0.107 (4)	0.089 (3)	0.007 (3)	0.030 (3)	−0.028 (3)
C7	0.094 (3)	0.116 (4)	0.092 (3)	0.012 (3)	0.037 (3)	−0.026 (3)
C8	0.089 (3)	0.063 (2)	0.080 (3)	0.001 (2)	0.042 (2)	−0.0070 (19)
C9	0.080 (3)	0.061 (2)	0.076 (2)	0.0038 (19)	0.036 (2)	0.0024 (19)
C10	0.080 (3)	0.058 (2)	0.082 (3)	−0.004 (2)	0.033 (2)	−0.006 (2)
C11	0.095 (3)	0.069 (3)	0.103 (3)	0.007 (2)	0.029 (3)	−0.015 (2)
C12	0.086 (3)	0.085 (3)	0.091 (3)	0.007 (2)	0.026 (2)	−0.016 (3)
C13	0.073 (2)	0.070 (3)	0.071 (2)	−0.002 (2)	0.032 (2)	0.001 (2)
C14	0.083 (3)	0.066 (3)	0.081 (2)	0.003 (2)	0.045 (2)	−0.004 (2)
C15	0.088 (3)	0.092 (3)	0.100 (3)	0.008 (3)	0.043 (3)	−0.008 (3)
C16	0.078 (3)	0.092 (3)	0.092 (3)	0.008 (2)	0.042 (2)	0.002 (3)
C17	0.083 (3)	0.079 (3)	0.079 (3)	−0.001 (2)	0.042 (2)	0.006 (2)
C18	0.089 (3)	0.106 (4)	0.086 (3)	−0.004 (3)	0.043 (2)	0.016 (3)
C19	0.083 (3)	0.087 (3)	0.086 (3)	0.002 (3)	0.042 (2)	0.004 (3)
C20	0.080 (3)	0.107 (4)	0.083 (3)	0.005 (3)	0.037 (2)	0.001 (3)
C21	0.095 (4)	0.165 (6)	0.090 (3)	0.026 (4)	0.030 (3)	−0.023 (4)
C22	0.101 (3)	0.111 (4)	0.086 (3)	−0.020 (3)	0.043 (3)	0.009 (3)
C23	0.104 (4)	0.121 (6)	0.213 (8)	0.009 (5)	−0.003 (4)	0.012 (6)
C24	0.097 (4)	0.165 (7)	0.101 (4)	0.024 (4)	0.023 (3)	0.010 (4)
C25	0.122 (5)	0.141 (6)	0.106 (4)	−0.010 (4)	0.014 (3)	−0.022 (4)
C26	0.103 (4)	0.083 (4)	0.154 (5)	−0.023 (3)	0.023 (3)	0.017 (4)

Geometric parameters (Å, º)

N1—C23	1.425 (9)	C12—H12A	0.97
N1—C3	1.468 (6)	C12—H12B	0.97
N1—H1N	0.90	C13—C18	1.536 (6)
N2—C24	1.457 (7)	C13—C17	1.550 (6)
N2—C20	1.478 (5)	C13—C14	1.556 (6)
N2—H2N	0.91	C14—C15	1.513 (7)
O1—C16	1.419 (5)	C14—C22	1.548 (7)
O1—H1O	0.82	C15—C16	1.542 (7)
C1—C10	1.499 (7)	C15—H15A	0.97
C1—C2	1.501 (6)	C15—H15B	0.97
C1—H1A	0.97	C16—C17	1.538 (7)
C1—H1B	0.97	C16—H16	0.98
C2—C3	1.516 (7)	C17—C20	1.519 (6)
C2—H2A	0.97	C17—H17	0.98
C2—H2B	0.97	C18—H18A	0.96
C3—C4	1.526 (7)	C18—H18B	0.96
C3—H3	0.98	C18—H18C	0.96
C4—C25	1.527 (7)	C19—H19A	0.97
C4—C26	1.528 (7)	C19—H19B	0.97
C4—C5	1.548 (6)	C20—C21	1.512 (8)
C5—C6	1.508 (7)	C20—H20	0.98
C5—C10	1.535 (6)	C21—H21A	0.96
C5—H5	0.98	C21—H21B	0.96
C6—C7	1.509 (7)	C21—H21C	0.96
C6—H6A	0.97	C22—H22A	0.96
C6—H6B	0.97	C22—H22B	0.96
C7—C8	1.520 (6)	C22—H22C	0.96
C7—H7A	0.97	C23—H23A	0.96
C7—H7B	0.97	C23—H23B	0.96
C8—C14	1.515 (6)	C23—H23C	0.96
C8—C9	1.559 (5)	C24—H24A	0.96
C8—H8	0.98	C24—H24B	0.96
C9—C19	1.502 (6)	C24—H24C	0.96
C9—C10	1.518 (6)	C25—H25A	0.96
C9—C11	1.526 (6)	C25—H25B	0.96
C10—C19	1.493 (6)	C25—H25C	0.96
C11—C12	1.534 (7)	C26—H26A	0.96
C11—H11A	0.97	C26—H26B	0.96
C11—H11B	0.97	C26—H26C	0.96
C12—C13	1.517 (7)
C23—N1—C3	115.4 (5)	C12—C13—C14	108.9 (4)
C23—N1—H1N	108.0	C18—C13—C14	111.2 (4)
C3—N1—H1N	107.7	C17—C13—C14	101.5 (3)
C24—N2—C20	113.4 (4)	C15—C14—C8	114.0 (4)
C24—N2—H2N	110.5	C15—C14—C22	107.5 (3)
C20—N2—H2N	110.9	C8—C14—C22	111.3 (4)
C16—O1—H1O	109.5	C15—C14—C13	101.9 (4)
C10—C1—C2	110.6 (4)	C8—C14—C13	110.4 (3)
C10—C1—H1A	109.5	C22—C14—C13	111.3 (4)
C2—C1—H1A	109.5	C14—C15—C16	106.4 (4)
C10—C1—H1B	109.5	C14—C15—H15A	110.4
C2—C1—H1B	109.5	C16—C15—H15A	110.4
H1A—C1—H1B	108.1	C14—C15—H15B	110.4
C1—C2—C3	112.6 (4)	C16—C15—H15B	110.4
C1—C2—H2A	109.1	H15A—C15—H15B	108.6
C3—C2—H2A	109.1	O1—C16—C17	109.6 (4)
C1—C2—H2B	109.1	O1—C16—C15	113.2 (3)
C3—C2—H2B	109.1	C17—C16—C15	106.0 (4)
H2A—C2—H2B	107.8	O1—C16—H16	109.3
N1—C3—C2	113.3 (4)	C17—C16—H16	109.3
N1—C3—C4	111.8 (4)	C15—C16—H16	109.3
C2—C3—C4	111.9 (4)	C20—C17—C16	112.8 (4)
N1—C3—H3	106.4	C20—C17—C13	118.9 (3)
C2—C3—H3	106.4	C16—C17—C13	104.0 (4)
C4—C3—H3	106.4	C20—C17—H17	106.8
C3—C4—C25	108.4 (5)	C16—C17—H17	106.8
C3—C4—C26	110.2 (4)	C13—C17—H17	106.8
C25—C4—C26	108.3 (5)	C13—C18—H18A	109.5
C3—C4—C5	108.1 (4)	C13—C18—H18B	109.5
C25—C4—C5	109.8 (4)	H18A—C18—H18B	109.5
C26—C4—C5	112.1 (4)	C13—C18—H18C	109.5
C6—C5—C10	112.8 (4)	H18A—C18—H18C	109.5
C6—C5—C4	116.0 (4)	H18B—C18—H18C	109.5
C10—C5—C4	112.7 (3)	C10—C19—C9	60.9 (3)
C6—C5—H5	104.7	C10—C19—H19A	117.7
C10—C5—H5	104.7	C9—C19—H19A	117.7
C4—C5—H5	104.7	C10—C19—H19B	117.7
C5—C6—C7	110.5 (5)	C9—C19—H19B	117.7
C5—C6—H6A	109.5	H19A—C19—H19B	114.8
C7—C6—H6A	109.5	N2—C20—C21	107.2 (4)
C5—C6—H6B	109.5	N2—C20—C17	107.8 (3)
C7—C6—H6B	109.5	C21—C20—C17	113.5 (5)
H6A—C6—H6B	108.1	N2—C20—H20	109.4
C6—C7—C8	111.2 (3)	C21—C20—H20	109.4
C6—C7—H7A	109.4	C17—C20—H20	109.4
C8—C7—H7A	109.4	C20—C21—H21A	109.5
C6—C7—H7B	109.4	C20—C21—H21B	109.5
C8—C7—H7B	109.4	H21A—C21—H21B	109.5
H7A—C7—H7B	108.0	C20—C21—H21C	109.5
C14—C8—C7	114.8 (3)	H21A—C21—H21C	109.5
C14—C8—C9	112.5 (3)	H21B—C21—H21C	109.5
C7—C8—C9	110.9 (4)	C14—C22—H22A	109.5
C14—C8—H8	105.9	C14—C22—H22B	109.5
C7—C8—H8	105.9	H22A—C22—H22B	109.5
C9—C8—H8	105.9	C14—C22—H22C	109.5
C19—C9—C10	59.3 (3)	H22A—C22—H22C	109.5
C19—C9—C11	119.7 (4)	H22B—C22—H22C	109.5
C10—C9—C11	117.2 (4)	N1—C23—H23A	109.5
C19—C9—C8	113.8 (4)	N1—C23—H23B	109.5
C10—C9—C8	118.8 (3)	H23A—C23—H23B	109.5
C11—C9—C8	116.1 (4)	N1—C23—H23C	109.5
C19—C10—C1	117.3 (4)	H23A—C23—H23C	109.5
C19—C10—C9	59.8 (3)	H23B—C23—H23C	109.5
C1—C10—C9	120.9 (4)	N2—C24—H24A	109.5
C19—C10—C5	121.6 (4)	N2—C24—H24B	109.5
C1—C10—C5	109.7 (4)	H24A—C24—H24B	109.5
C9—C10—C5	120.0 (3)	N2—C24—H24C	109.5
C9—C11—C12	117.2 (4)	H24A—C24—H24C	109.5
C9—C11—H11A	108.0	H24B—C24—H24C	109.5
C12—C11—H11A	108.0	C4—C25—H25A	109.5
C9—C11—H11B	108.0	C4—C25—H25B	109.5
C12—C11—H11B	108.0	H25A—C25—H25B	109.5
H11A—C11—H11B	107.2	C4—C25—H25C	109.5
C13—C12—C11	114.7 (4)	H25A—C25—H25C	109.5
C13—C12—H12A	108.6	H25B—C25—H25C	109.5
C11—C12—H12A	108.6	C4—C26—H26A	109.5
C13—C12—H12B	108.6	C4—C26—H26B	109.5
C11—C12—H12B	108.6	H26A—C26—H26B	109.5
H12A—C12—H12B	107.6	C4—C26—H26C	109.5
C12—C13—C18	108.1 (3)	H26A—C26—H26C	109.5
C12—C13—C17	117.4 (4)	H26B—C26—H26C	109.5
C18—C13—C17	109.7 (4)
C10—C1—C2—C3	−57.1 (6)	C10—C9—C11—C12	173.9 (4)
C23—N1—C3—C2	83.5 (7)	C8—C9—C11—C12	−37.5 (6)
C23—N1—C3—C4	−148.8 (6)	C9—C11—C12—C13	13.6 (6)
C1—C2—C3—N1	−176.1 (4)	C11—C12—C13—C18	−83.3 (5)
C1—C2—C3—C4	56.3 (6)	C11—C12—C13—C17	152.1 (4)
N1—C3—C4—C25	59.0 (5)	C11—C12—C13—C14	37.6 (5)
C2—C3—C4—C25	−172.6 (4)	C7—C8—C14—C15	−72.4 (5)
N1—C3—C4—C26	−59.3 (6)	C9—C8—C14—C15	159.5 (3)
C2—C3—C4—C26	69.1 (5)	C7—C8—C14—C22	49.4 (5)
N1—C3—C4—C5	177.9 (4)	C9—C8—C14—C22	−78.7 (4)
C2—C3—C4—C5	−53.7 (5)	C7—C8—C14—C13	173.6 (4)
C3—C4—C5—C6	−172.4 (4)	C9—C8—C14—C13	45.4 (5)
C25—C4—C5—C6	−54.4 (6)	C12—C13—C14—C15	169.1 (4)
C26—C4—C5—C6	66.0 (5)	C18—C13—C14—C15	−71.9 (4)
C3—C4—C5—C10	55.5 (5)	C17—C13—C14—C15	44.7 (4)
C25—C4—C5—C10	173.5 (5)	C12—C13—C14—C8	−69.5 (4)
C26—C4—C5—C10	−66.1 (6)	C18—C13—C14—C8	49.5 (5)
C10—C5—C6—C7	−50.4 (5)	C17—C13—C14—C8	166.1 (3)
C4—C5—C6—C7	177.6 (4)	C12—C13—C14—C22	54.7 (5)
C5—C6—C7—C8	69.0 (6)	C18—C13—C14—C22	173.7 (4)
C6—C7—C8—C14	177.4 (5)	C17—C13—C14—C22	−69.7 (4)
C6—C7—C8—C9	−53.6 (6)	C8—C14—C15—C16	−152.9 (3)
C14—C8—C9—C19	−138.7 (4)	C22—C14—C15—C16	83.2 (4)
C7—C8—C9—C19	91.1 (4)	C13—C14—C15—C16	−33.9 (4)
C14—C8—C9—C10	154.5 (3)	C14—C15—C16—O1	−110.1 (5)
C7—C8—C9—C10	24.4 (5)	C14—C15—C16—C17	10.0 (5)
C14—C8—C9—C11	6.4 (5)	O1—C16—C17—C20	−89.3 (4)
C7—C8—C9—C11	−123.7 (4)	C15—C16—C17—C20	148.3 (4)
C2—C1—C10—C19	−87.3 (5)	O1—C16—C17—C13	140.6 (4)
C2—C1—C10—C9	−156.8 (4)	C15—C16—C17—C13	18.1 (4)
C2—C1—C10—C5	56.8 (5)	C12—C13—C17—C20	76.5 (6)
C11—C9—C10—C19	−110.1 (4)	C18—C13—C17—C20	−47.3 (6)
C8—C9—C10—C19	102.1 (4)	C14—C13—C17—C20	−165.0 (5)
C19—C9—C10—C1	105.7 (5)	C12—C13—C17—C16	−157.1 (4)
C11—C9—C10—C1	−4.4 (6)	C18—C13—C17—C16	79.1 (4)
C8—C9—C10—C1	−152.2 (4)	C14—C13—C17—C16	−38.6 (4)
C19—C9—C10—C5	−111.3 (5)	C1—C10—C19—C9	−111.6 (4)
C11—C9—C10—C5	138.6 (4)	C5—C10—C19—C9	108.7 (4)
C8—C9—C10—C5	−9.2 (5)	C11—C9—C19—C10	105.8 (4)
C6—C5—C10—C19	−49.2 (5)	C8—C9—C19—C10	−110.4 (4)
C4—C5—C10—C19	84.5 (5)	C24—N2—C20—C21	77.0 (6)
C6—C5—C10—C1	168.5 (4)	C24—N2—C20—C17	−160.4 (5)
C4—C5—C10—C1	−57.8 (5)	C16—C17—C20—N2	61.4 (6)
C6—C5—C10—C9	21.8 (5)	C13—C17—C20—N2	−176.5 (4)
C4—C5—C10—C9	155.4 (4)	C16—C17—C20—C21	180.0 (4)
C19—C9—C11—C12	105.5 (5)	C13—C17—C20—C21	−57.9 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1	0.91	2.24	2.982 (6)	139
C25—H25A···N1	0.96	2.52	2.905 (9)	104
C26—H26A···N1	0.96	2.55	2.945 (8)	105