Dehydro­abietic acid N-methyl­anilide

The title compound, C₂₇H₃₅NO [systematic name: (1R,4aS,10aR)-7-iso­propyl-N,1,4a-trimethyl-N-phenyl-1,2,3,4,4a,9,10,10a-octa­hydro­phenanthrene-1-carboxamide], has been syn­thesized from dehydro­abietic acid. The two cyclo­hexane rings form a trans ring junction with classical chair and half-boat conformations, each somewhat deformed towards a half-chair conformation.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.064
• wR factor = 0.179
• Data-to-parameter ratio = 10.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.71 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.39 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C3
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

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           26.99
           From the CIF: _reflns_number_total               2680
           Count of symmetry unique reflns         2688
           Completeness (_total/calc)             99.70%
           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
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13    = .          S

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

   6 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
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97.

Dehydroabietic acid N-methyl-anilide

Crystal data

C27H35NO	F(000) = 424
Mr = 389.56	Dx = 1.145 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 10.460 (2) Å	Cell parameters from 25 reflections
b = 6.7200 (13) Å	θ = 10–13°
c = 16.086 (3) Å	µ = 0.07 mm^−1
β = 91.30 (3)°	T = 293 K
V = 1130.4 (4) Å^3	Block, colourless
Z = 2	0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	1891 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
Graphite monochromator	θmax = 27.0°, θmin = 1.3°
ω/2θ scans	h = −13→13
Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995)	k = −8→0
Tmin = 0.980, Tmax = 0.993	l = −20→0
2771 measured reflections	3 standard reflections every 200 reflections
2680 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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.179	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.1P)^2 + 0.2P] where P = (Fo^2 + 2Fc^2)/3
2680 reflections	(Δ/σ)max = 0.025
262 parameters	Δρmax = 0.20 e Å^−3
22 restraints	Δρmin = −0.24 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
N	0.6719 (3)	0.4114 (5)	0.44181 (19)	0.0474 (8)
O	0.5173 (4)	0.1956 (7)	0.4171 (2)	0.0931 (15)
C1	−0.1332 (5)	−0.1796 (12)	0.1022 (5)	0.116 (2)
H1A	−0.1355	−0.0554	0.0727	0.173*
H1B	−0.1508	−0.1567	0.1597	0.173*
H1C	−0.1965	−0.2679	0.0787	0.173*
C2	0.0070 (6)	−0.4631 (9)	0.1400 (4)	0.0878 (17)
H2A	−0.0654	−0.5461	0.1269	0.132*
H2B	0.0114	−0.4395	0.1989	0.132*
H2C	0.0838	−0.5282	0.1231	0.132*
C3	−0.0068 (4)	−0.2691 (8)	0.0952 (3)	0.0705 (14)
H3A	0.0002	−0.3027	0.0362	0.085*
C4	0.1045 (4)	−0.1286 (7)	0.1137 (3)	0.0602 (12)
C5	0.2039 (4)	−0.1160 (8)	0.0604 (3)	0.0632 (12)
H5A	0.2020	−0.1908	0.0118	0.076*
C6	0.3069 (4)	0.0056 (8)	0.0776 (3)	0.0607 (12)
H6A	0.3721	0.0122	0.0394	0.073*
C7	0.3176 (4)	0.1198 (6)	0.1502 (2)	0.0461 (9)
C8	0.4325 (4)	0.2568 (6)	0.1658 (2)	0.0467 (9)
C9	0.5551 (4)	0.1616 (7)	0.1334 (3)	0.0580 (12)
H9A	0.5625	0.0269	0.1546	0.070*
H9B	0.5498	0.1546	0.0732	0.070*
C10	0.6731 (4)	0.2794 (9)	0.1596 (3)	0.0623 (12)
H10A	0.6667	0.4133	0.1374	0.075*
H10B	0.7483	0.2174	0.1368	0.075*
C11	0.6877 (4)	0.2891 (9)	0.2538 (3)	0.0584 (12)
H11A	0.7641	0.3644	0.2683	0.070*
H11B	0.6990	0.1553	0.2754	0.070*
C12	0.5726 (4)	0.3855 (7)	0.2956 (2)	0.0475 (10)
C13	0.4474 (3)	0.2856 (6)	0.2608 (2)	0.0429 (9)
H13A	0.4505	0.1499	0.2831	0.051*
C14	0.3263 (4)	0.3737 (7)	0.2956 (3)	0.0542 (10)
H14A	0.3042	0.4953	0.2662	0.065*
H14B	0.3398	0.4056	0.3540	0.065*
C15	0.2177 (4)	0.2233 (8)	0.2858 (3)	0.0609 (12)
H15A	0.2234	0.1295	0.3316	0.073*
H15B	0.1370	0.2933	0.2899	0.073*
C16	0.2168 (4)	0.1087 (7)	0.2054 (2)	0.0493 (10)
C17	0.1125 (4)	−0.0161 (8)	0.1862 (3)	0.0590 (11)
H17A	0.0461	−0.0238	0.2235	0.071*
C18	0.4052 (5)	0.4488 (8)	0.1145 (3)	0.0643 (13)
H18A	0.3974	0.4157	0.0565	0.097*
H18B	0.4743	0.5412	0.1229	0.097*
H18C	0.3270	0.5081	0.1324	0.097*
C19	0.5709 (5)	0.6125 (7)	0.2822 (3)	0.0629 (13)
H19A	0.6489	0.6691	0.3041	0.094*
H19B	0.4996	0.6692	0.3103	0.094*
H19C	0.5632	0.6407	0.2238	0.094*
C20	0.5842 (4)	0.3286 (7)	0.3890 (2)	0.0503 (10)
C21	0.6704 (4)	0.3456 (8)	0.5290 (2)	0.0550 (11)
H21A	0.6062	0.2449	0.5351	0.083*
H21B	0.6514	0.4567	0.5641	0.083*
H21C	0.7525	0.2920	0.5446	0.083*
C22	0.7655 (4)	0.5628 (6)	0.4258 (2)	0.0432 (9)
C23	0.8851 (4)	0.5126 (7)	0.3991 (3)	0.0528 (10)
H23A	0.9043	0.3804	0.3877	0.063*
C24	0.9769 (4)	0.6574 (9)	0.3893 (3)	0.0623 (13)
H24A	1.0576	0.6223	0.3711	0.075*
C25	0.9499 (5)	0.8533 (8)	0.4062 (3)	0.0651 (13)
H25A	1.0113	0.9512	0.3982	0.078*
C26	0.8316 (5)	0.9029 (8)	0.4348 (3)	0.0694 (13)
H26A	0.8138	1.0349	0.4475	0.083*
C27	0.7388 (4)	0.7603 (7)	0.4451 (3)	0.0586 (12)
H27A	0.6589	0.7955	0.4647	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N	0.0506 (17)	0.0465 (19)	0.0454 (17)	−0.0047 (17)	0.0030 (14)	−0.0010 (16)
O	0.105 (3)	0.114 (4)	0.0598 (19)	−0.068 (3)	−0.0170 (17)	0.034 (2)
C1	0.074 (3)	0.086 (4)	0.186 (6)	−0.004 (3)	−0.015 (4)	−0.013 (5)
C2	0.087 (3)	0.067 (3)	0.108 (4)	−0.025 (3)	−0.021 (3)	0.018 (3)
C3	0.059 (2)	0.062 (3)	0.090 (3)	−0.012 (2)	−0.016 (2)	0.006 (3)
C4	0.057 (2)	0.046 (3)	0.076 (3)	−0.007 (2)	−0.021 (2)	0.007 (2)
C5	0.066 (3)	0.060 (3)	0.063 (3)	−0.010 (3)	−0.007 (2)	−0.007 (2)
C6	0.062 (2)	0.068 (3)	0.052 (2)	−0.017 (3)	−0.0036 (19)	−0.005 (2)
C7	0.050 (2)	0.039 (2)	0.049 (2)	−0.0056 (19)	−0.0026 (17)	0.0044 (19)
C8	0.052 (2)	0.043 (2)	0.045 (2)	−0.0114 (19)	0.0044 (16)	0.0026 (18)
C9	0.061 (2)	0.060 (3)	0.053 (2)	−0.013 (2)	0.0108 (19)	−0.009 (2)
C10	0.051 (2)	0.075 (3)	0.062 (3)	−0.010 (2)	0.0137 (18)	−0.010 (3)
C11	0.045 (2)	0.071 (3)	0.059 (2)	−0.015 (2)	0.0021 (17)	−0.002 (2)
C12	0.049 (2)	0.045 (2)	0.048 (2)	−0.015 (2)	0.0000 (17)	0.0026 (19)
C13	0.0452 (19)	0.041 (2)	0.0423 (19)	−0.0094 (18)	0.0021 (15)	0.0049 (18)
C14	0.058 (2)	0.052 (3)	0.053 (2)	−0.004 (2)	0.0040 (18)	−0.003 (2)
C15	0.046 (2)	0.079 (4)	0.058 (2)	−0.008 (2)	0.0064 (18)	0.003 (2)
C16	0.052 (2)	0.047 (2)	0.048 (2)	−0.005 (2)	−0.0039 (17)	0.007 (2)
C17	0.050 (2)	0.059 (3)	0.068 (3)	−0.007 (2)	0.0013 (19)	0.013 (2)
C18	0.077 (3)	0.057 (3)	0.059 (3)	−0.017 (3)	−0.007 (2)	0.013 (2)
C19	0.084 (3)	0.046 (3)	0.059 (3)	−0.021 (2)	−0.004 (2)	0.001 (2)
C20	0.050 (2)	0.054 (3)	0.047 (2)	−0.017 (2)	0.0018 (17)	0.003 (2)
C21	0.059 (2)	0.060 (3)	0.046 (2)	0.002 (2)	0.0027 (17)	0.002 (2)
C22	0.043 (2)	0.042 (2)	0.0438 (19)	−0.0047 (18)	−0.0004 (16)	−0.0071 (17)
C23	0.050 (2)	0.045 (2)	0.063 (2)	0.002 (2)	0.0008 (19)	−0.008 (2)
C24	0.039 (2)	0.079 (4)	0.069 (3)	−0.009 (2)	0.0031 (19)	−0.014 (3)
C25	0.065 (3)	0.057 (3)	0.073 (3)	−0.025 (3)	−0.003 (2)	−0.004 (3)
C26	0.078 (3)	0.040 (2)	0.090 (3)	−0.007 (3)	−0.001 (3)	−0.017 (3)
C27	0.053 (2)	0.054 (3)	0.069 (3)	0.002 (2)	0.005 (2)	−0.021 (2)

Geometric parameters (Å, º)

N—C20	1.355 (5)	C12—C19	1.541 (7)
N—C22	1.440 (5)	C12—C20	1.551 (5)
N—C21	1.471 (5)	C12—C13	1.565 (5)
O—C20	1.228 (5)	C13—C14	1.518 (5)
C1—C3	1.459 (8)	C13—H13A	0.9800
C1—H1A	0.9600	C14—C15	1.526 (6)
C1—H1B	0.9600	C14—H14A	0.9700
C1—H1C	0.9600	C14—H14B	0.9700
C2—C3	1.494 (8)	C15—C16	1.505 (6)
C2—H2A	0.9600	C15—H15A	0.9700
C2—H2B	0.9600	C15—H15B	0.9700
C2—H2C	0.9600	C16—C17	1.405 (6)
C3—C4	1.523 (6)	C17—H17A	0.9300
C3—H3A	0.9800	C18—H18A	0.9600
C4—C5	1.366 (6)	C18—H18B	0.9600
C4—C17	1.391 (7)	C18—H18C	0.9600
C5—C6	1.375 (6)	C19—H19A	0.9600
C5—H5A	0.9300	C19—H19B	0.9600
C6—C7	1.399 (6)	C19—H19C	0.9600
C6—H6A	0.9300	C21—H21A	0.9600
C7—C16	1.396 (5)	C21—H21B	0.9600
C7—C8	1.531 (5)	C21—H21C	0.9600
C8—C9	1.534 (6)	C22—C23	1.374 (5)
C8—C13	1.545 (5)	C22—C27	1.393 (6)
C8—C18	1.554 (6)	C23—C24	1.378 (6)
C9—C10	1.518 (6)	C23—H23A	0.9300
C9—H9A	0.9700	C24—C25	1.375 (8)
C9—H9B	0.9700	C24—H24A	0.9300
C10—C11	1.521 (6)	C25—C26	1.371 (7)
C10—H10A	0.9700	C25—H25A	0.9300
C10—H10B	0.9700	C26—C27	1.377 (6)
C11—C12	1.535 (6)	C26—H26A	0.9300
C11—H11A	0.9700	C27—H27A	0.9300
C11—H11B	0.9700
C20—N—C22	129.1 (3)	C14—C13—C8	110.4 (3)
C20—N—C21	116.9 (3)	C14—C13—C12	113.5 (3)
C22—N—C21	113.9 (3)	C8—C13—C12	118.2 (3)
C3—C1—H1A	109.5	C14—C13—H13A	104.3
C3—C1—H1B	109.5	C8—C13—H13A	104.3
H1A—C1—H1B	109.5	C12—C13—H13A	104.3
C3—C1—H1C	109.5	C13—C14—C15	109.2 (4)
H1A—C1—H1C	109.5	C13—C14—H14A	109.8
H1B—C1—H1C	109.5	C15—C14—H14A	109.8
C3—C2—H2A	109.5	C13—C14—H14B	109.8
C3—C2—H2B	109.5	C15—C14—H14B	109.8
H2A—C2—H2B	109.5	H14A—C14—H14B	108.3
C3—C2—H2C	109.5	C16—C15—C14	114.7 (3)
H2A—C2—H2C	109.5	C16—C15—H15A	108.6
H2B—C2—H2C	109.5	C14—C15—H15A	108.6
C1—C3—C2	113.6 (5)	C16—C15—H15B	108.6
C1—C3—C4	114.8 (5)	C14—C15—H15B	108.6
C2—C3—C4	112.4 (4)	H15A—C15—H15B	107.6
C1—C3—H3A	104.9	C7—C16—C17	119.1 (4)
C2—C3—H3A	104.9	C7—C16—C15	122.0 (4)
C4—C3—H3A	104.9	C17—C16—C15	119.0 (4)
C5—C4—C17	117.4 (4)	C4—C17—C16	122.8 (4)
C5—C4—C3	120.4 (5)	C4—C17—H17A	118.6
C17—C4—C3	122.1 (4)	C16—C17—H17A	118.6
C4—C5—C6	121.0 (4)	C8—C18—H18A	109.5
C4—C5—H5A	119.5	C8—C18—H18B	109.5
C6—C5—H5A	119.5	H18A—C18—H18B	109.5
C5—C6—C7	122.8 (4)	C8—C18—H18C	109.5
C5—C6—H6A	118.6	H18A—C18—H18C	109.5
C7—C6—H6A	118.6	H18B—C18—H18C	109.5
C16—C7—C6	117.0 (4)	C12—C19—H19A	109.5
C16—C7—C8	122.0 (4)	C12—C19—H19B	109.5
C6—C7—C8	121.0 (3)	H19A—C19—H19B	109.5
C7—C8—C9	110.7 (3)	C12—C19—H19C	109.5
C7—C8—C13	107.4 (3)	H19A—C19—H19C	109.5
C9—C8—C13	108.8 (3)	H19B—C19—H19C	109.5
C7—C8—C18	106.1 (3)	O—C20—N	116.8 (4)
C9—C8—C18	108.1 (3)	O—C20—C12	120.2 (4)
C13—C8—C18	115.7 (4)	N—C20—C12	122.9 (3)
C10—C9—C8	111.6 (4)	N—C21—H21A	109.5
C10—C9—H9A	109.3	N—C21—H21B	109.5
C8—C9—H9A	109.3	H21A—C21—H21B	109.5
C10—C9—H9B	109.3	N—C21—H21C	109.5
C8—C9—H9B	109.3	H21A—C21—H21C	109.5
H9A—C9—H9B	108.0	H21B—C21—H21C	109.5
C9—C10—C11	111.2 (4)	C23—C22—C27	119.5 (4)
C9—C10—H10A	109.4	C23—C22—N	120.7 (4)
C11—C10—H10A	109.4	C27—C22—N	119.5 (3)
C9—C10—H10B	109.4	C22—C23—C24	120.2 (4)
C11—C10—H10B	109.4	C22—C23—H23A	119.9
H10A—C10—H10B	108.0	C24—C23—H23A	119.9
C10—C11—C12	113.1 (4)	C25—C24—C23	120.5 (4)
C10—C11—H11A	108.9	C25—C24—H24A	119.8
C12—C11—H11A	108.9	C23—C24—H24A	119.8
C10—C11—H11B	108.9	C26—C25—C24	119.3 (4)
C12—C11—H11B	108.9	C26—C25—H25A	120.3
H11A—C11—H11B	107.8	C24—C25—H25A	120.3
C11—C12—C19	111.3 (4)	C25—C26—C27	121.0 (5)
C11—C12—C20	106.0 (3)	C25—C26—H26A	119.5
C19—C12—C20	112.4 (4)	C27—C26—H26A	119.5
C11—C12—C13	108.7 (3)	C26—C27—C22	119.4 (4)
C19—C12—C13	111.5 (4)	C26—C27—H27A	120.3
C20—C12—C13	106.7 (3)	C22—C27—H27A	120.3
C1—C3—C4—C5	−131.1 (6)	C8—C13—C14—C15	66.1 (4)
C2—C3—C4—C5	97.0 (6)	C12—C13—C14—C15	−158.4 (3)
C1—C3—C4—C17	52.0 (7)	C13—C14—C15—C16	−39.1 (5)
C2—C3—C4—C17	−80.0 (6)	C6—C7—C16—C17	0.8 (6)
C17—C4—C5—C6	−0.9 (7)	C8—C7—C16—C17	178.3 (4)
C3—C4—C5—C6	−178.0 (4)	C6—C7—C16—C15	179.5 (4)
C4—C5—C6—C7	1.2 (8)	C8—C7—C16—C15	−3.0 (6)
C5—C6—C7—C16	−1.1 (7)	C14—C15—C16—C7	8.7 (6)
C5—C6—C7—C8	−178.6 (4)	C14—C15—C16—C17	−172.7 (4)
C16—C7—C8—C9	145.7 (4)	C5—C4—C17—C16	0.7 (7)
C6—C7—C8—C9	−36.9 (5)	C3—C4—C17—C16	177.7 (4)
C16—C7—C8—C13	27.2 (5)	C7—C16—C17—C4	−0.7 (6)
C6—C7—C8—C13	−155.5 (4)	C15—C16—C17—C4	−179.4 (4)
C16—C7—C8—C18	−97.2 (4)	C22—N—C20—O	177.4 (4)
C6—C7—C8—C18	80.2 (5)	C21—N—C20—O	−5.0 (6)
C7—C8—C9—C10	−171.4 (4)	C22—N—C20—C12	1.5 (7)
C13—C8—C9—C10	−53.6 (5)	C21—N—C20—C12	179.0 (4)
C18—C8—C9—C10	72.8 (4)	C11—C12—C20—O	−102.2 (5)
C8—C9—C10—C11	60.7 (6)	C19—C12—C20—O	136.1 (5)
C9—C10—C11—C12	−59.0 (6)	C13—C12—C20—O	13.5 (6)
C10—C11—C12—C19	−73.7 (5)	C11—C12—C20—N	73.7 (5)
C10—C11—C12—C20	163.9 (4)	C19—C12—C20—N	−48.1 (6)
C10—C11—C12—C13	49.5 (5)	C13—C12—C20—N	−170.6 (4)
C7—C8—C13—C14	−58.4 (4)	C20—N—C22—C23	−89.1 (5)
C9—C8—C13—C14	−178.2 (4)	C21—N—C22—C23	93.4 (4)
C18—C8—C13—C14	59.9 (4)	C20—N—C22—C27	97.1 (5)
C7—C8—C13—C12	168.5 (4)	C21—N—C22—C27	−80.5 (5)
C9—C8—C13—C12	48.7 (5)	C27—C22—C23—C24	−1.8 (6)
C18—C8—C13—C12	−73.2 (5)	N—C22—C23—C24	−175.6 (4)
C11—C12—C13—C14	−178.1 (4)	C22—C23—C24—C25	0.1 (7)
C19—C12—C13—C14	−55.1 (5)	C23—C24—C25—C26	1.5 (8)
C20—C12—C13—C14	68.0 (4)	C24—C25—C26—C27	−1.5 (8)
C11—C12—C13—C8	−46.4 (5)	C25—C26—C27—C22	−0.2 (7)
C19—C12—C13—C8	76.6 (5)	C23—C22—C27—C26	1.8 (7)
C20—C12—C13—C8	−160.3 (4)	N—C22—C27—C26	175.7 (4)