4-Chloro-2-{(E)-[(1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octa­hydro­phenanthren-1-yl]methyl­imino­meth­yl}phenol

The title compound, C₂₇H₃₄ClNO, was synthesized by a direct condensation reaction. The mol­ecule has three chiral centres, which exhibit R, S and R absolute configurations, respectively. Two six-membered rings with different conformations coexist in the structure and they form a trans ring junction with two methyl groups in axial positions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.060
• wR factor = 0.160
• Data-to-parameter ratio = 9.2

checkCIF/PLATON results

No syntax errors found



Alert level A
DIFF020_ALERT_1_A  _diffrn_standards_interval_count and
            _diffrn_standards_interval_time are missing. Number of measurements
            between standards or time (min) between standards.
DIFF022_ALERT_1_A  _diffrn_standards_decay_% is missing
            Percentage decrease in standards intensity.

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.02 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H14C   ..  H15B    ..       1.84 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           25.99
           From the CIF: _reflns_number_total               2526
           Count of symmetry unique reflns         2527
           Completeness (_total/calc)             99.96%
           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        yes
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 C12    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C16    = .          R

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

   8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

4-Chloro-2-{(E)-[(1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl- 1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl]methyliminomethyl}phenol monohydrate

Crystal data

C27H34ClNO	F(000) = 456
Mr = 424.00	Dx = 1.204 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 11.249 (2) Å	θ = 10–13°
b = 6.1790 (12) Å	µ = 0.18 mm^−1
c = 17.276 (4) Å	T = 293 K
β = 103.04 (3)°	Block, yellow
V = 1169.8 (4) Å^3	0.40 × 0.30 × 0.10 mm
Z = 2

Data collection

Siemens SMART 1000 diffractometer	2526 independent reflections
Radiation source: fine-focus sealed tube	1639 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 26.0°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = 0→13
Tmin = 0.931, Tmax = 0.982	k = 0→7
2657 measured reflections	l = −21→20

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.061	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.160	w = 1/[σ^2(Fo^2) + (0.08P)^2 + 0.0497P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.025
2526 reflections	Δρmax = 0.19 e Å^−3
275 parameters	Δρmin = −0.24 e Å^−3
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.07 (18)

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
Cl	−0.38523 (12)	0.0639 (4)	0.47855 (10)	0.1057 (7)
O	0.0401 (4)	−0.4379 (7)	0.6401 (2)	0.0752 (11)
N	0.1723 (3)	−0.1030 (7)	0.6302 (2)	0.0537 (10)
C1	0.9632 (5)	0.8406 (11)	0.8440 (4)	0.097 (2)
H1A	1.0374	0.9234	0.8536	0.145*
H1B	0.9012	0.9213	0.8615	0.145*
H1C	0.9370	0.8113	0.7882	0.145*
C2	1.0940 (4)	0.5100 (13)	0.8750 (4)	0.102 (2)
H2A	1.1633	0.6050	0.8837	0.154*
H2B	1.0772	0.4577	0.8213	0.154*
H2C	1.1112	0.3899	0.9110	0.154*
C3	0.9855 (5)	0.6307 (10)	0.8889 (3)	0.0714 (16)
H3A	1.0051	0.6698	0.9453	0.086*
C4	0.8716 (4)	0.4887 (9)	0.8765 (3)	0.0556 (13)
C5	0.8193 (4)	0.4032 (9)	0.8027 (3)	0.0586 (13)
H5A	0.8546	0.4335	0.7601	0.070*
C6	0.7144 (4)	0.2715 (9)	0.7898 (3)	0.0515 (12)
C7	0.6607 (4)	0.2278 (7)	0.8531 (2)	0.0439 (11)
C8	0.7144 (4)	0.3145 (9)	0.9262 (3)	0.0520 (12)
H8A	0.6800	0.2853	0.9692	0.062*
C9	0.8179 (4)	0.4440 (9)	0.9380 (3)	0.0573 (13)
H9A	0.8508	0.5004	0.9881	0.069*
C10	0.6655 (4)	0.1828 (11)	0.7085 (3)	0.0681 (16)
H10A	0.7330	0.1277	0.6879	0.082*
H10B	0.6279	0.2996	0.6740	0.082*
C11	0.5713 (4)	0.0008 (10)	0.7056 (3)	0.0596 (13)
H11A	0.5272	−0.0230	0.6511	0.072*
H11B	0.6124	−0.1326	0.7255	0.072*
C12	0.4826 (3)	0.0657 (7)	0.7564 (2)	0.0429 (10)
H12A	0.4619	0.2165	0.7417	0.051*
C13	0.5503 (4)	0.0765 (8)	0.8454 (2)	0.0451 (10)
C14	0.6022 (4)	−0.1422 (8)	0.8815 (3)	0.0591 (13)
H14A	0.6425	−0.1218	0.9362	0.089*
H14B	0.6596	−0.1964	0.8527	0.089*
H14C	0.5368	−0.2442	0.8779	0.089*
C15	0.3722 (5)	−0.3047 (8)	0.7434 (3)	0.0641 (14)
H15A	0.2930	−0.3711	0.7314	0.096*
H15B	0.4144	−0.3434	0.7963	0.096*
H15C	0.4181	−0.3539	0.7062	0.096*
C16	0.3579 (4)	−0.0546 (7)	0.7374 (3)	0.0476 (11)
C17	0.2797 (4)	0.0304 (9)	0.7923 (3)	0.0547 (12)
H17A	0.2535	0.1762	0.7760	0.066*
H17B	0.2072	−0.0589	0.7857	0.066*
C18	0.3420 (4)	0.0343 (10)	0.8785 (3)	0.0601 (13)
H18A	0.3589	−0.1129	0.8973	0.072*
H18B	0.2879	0.0989	0.9085	0.072*
C19	0.4607 (4)	0.1615 (9)	0.8934 (2)	0.0517 (12)
H19A	0.4993	0.1549	0.9496	0.062*
H19B	0.4425	0.3121	0.8798	0.062*
C20	0.2916 (4)	0.0005 (9)	0.6514 (3)	0.0557 (12)
H20A	0.2817	0.1561	0.6460	0.067*
H20B	0.3408	−0.0473	0.6152	0.067*
C21	0.0783 (4)	0.0008 (9)	0.5982 (3)	0.0523 (11)
H21A	0.0854	0.1462	0.5861	0.063*
C22	−0.0415 (4)	−0.0998 (8)	0.5795 (3)	0.0493 (11)
C23	−0.1435 (4)	0.0105 (9)	0.5403 (3)	0.0552 (12)
H23A	−0.1350	0.1512	0.5231	0.066*
C24	−0.2574 (4)	−0.0811 (10)	0.5257 (3)	0.0636 (15)
C25	−0.2721 (5)	−0.2928 (11)	0.5504 (3)	0.0678 (16)
H25A	−0.3492	−0.3554	0.5409	0.081*
C26	−0.1722 (5)	−0.4068 (10)	0.5886 (3)	0.0669 (14)
H26A	−0.1824	−0.5474	0.6051	0.080*
C27	−0.0561 (5)	−0.3187 (8)	0.6034 (3)	0.0552 (13)
H0A	0.111 (5)	−0.361 (13)	0.650 (4)	0.10 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.0612 (8)	0.1275 (17)	0.1225 (13)	0.0092 (11)	0.0084 (8)	0.0399 (14)
O	0.081 (3)	0.045 (2)	0.091 (3)	−0.009 (2)	0.002 (2)	0.013 (2)
N	0.057 (2)	0.038 (2)	0.063 (2)	−0.007 (2)	0.007 (2)	0.0047 (19)
C1	0.082 (4)	0.055 (4)	0.154 (6)	−0.013 (4)	0.028 (4)	0.018 (4)
C2	0.059 (3)	0.079 (5)	0.167 (7)	−0.008 (4)	0.020 (4)	−0.002 (5)
C3	0.058 (3)	0.060 (4)	0.092 (4)	−0.007 (3)	0.008 (3)	−0.001 (3)
C4	0.046 (2)	0.042 (3)	0.076 (3)	0.001 (2)	0.005 (2)	−0.004 (3)
C5	0.057 (3)	0.055 (3)	0.068 (3)	−0.012 (3)	0.022 (2)	0.006 (3)
C6	0.054 (3)	0.047 (3)	0.054 (3)	0.000 (2)	0.015 (2)	0.002 (2)
C7	0.045 (2)	0.038 (3)	0.049 (2)	0.006 (2)	0.0118 (19)	0.005 (2)
C8	0.054 (3)	0.048 (3)	0.053 (3)	0.002 (3)	0.010 (2)	−0.001 (2)
C9	0.064 (3)	0.047 (3)	0.058 (3)	0.002 (2)	0.009 (2)	−0.005 (2)
C10	0.065 (3)	0.086 (4)	0.060 (3)	−0.024 (3)	0.028 (2)	−0.011 (3)
C11	0.057 (3)	0.067 (4)	0.058 (3)	−0.006 (3)	0.019 (2)	−0.015 (3)
C12	0.051 (2)	0.030 (2)	0.050 (2)	0.000 (2)	0.0166 (19)	0.003 (2)
C13	0.049 (2)	0.035 (2)	0.053 (2)	0.004 (2)	0.0160 (19)	0.007 (2)
C14	0.061 (3)	0.040 (3)	0.072 (3)	0.000 (2)	0.006 (2)	0.014 (3)
C15	0.069 (3)	0.030 (3)	0.090 (4)	−0.005 (3)	0.010 (3)	0.005 (3)
C16	0.048 (2)	0.035 (3)	0.062 (3)	−0.003 (2)	0.016 (2)	0.009 (2)
C17	0.050 (2)	0.053 (3)	0.062 (3)	−0.003 (3)	0.016 (2)	0.008 (3)
C18	0.057 (3)	0.063 (4)	0.067 (3)	0.002 (3)	0.028 (2)	0.005 (3)
C19	0.058 (3)	0.049 (3)	0.052 (3)	−0.004 (2)	0.020 (2)	0.005 (2)
C20	0.056 (3)	0.045 (3)	0.066 (3)	−0.006 (3)	0.012 (2)	0.006 (2)
C21	0.062 (3)	0.037 (3)	0.056 (3)	−0.006 (3)	0.009 (2)	0.006 (2)
C22	0.057 (3)	0.041 (3)	0.049 (3)	−0.004 (2)	0.011 (2)	−0.002 (2)
C23	0.063 (3)	0.043 (3)	0.061 (3)	−0.004 (3)	0.018 (2)	0.004 (2)
C24	0.058 (3)	0.074 (4)	0.061 (3)	0.003 (3)	0.017 (2)	0.003 (3)
C25	0.058 (3)	0.083 (4)	0.064 (3)	−0.020 (3)	0.015 (3)	−0.004 (3)
C26	0.082 (4)	0.048 (3)	0.072 (3)	−0.023 (3)	0.018 (3)	−0.006 (3)
C27	0.068 (3)	0.043 (3)	0.053 (3)	−0.011 (3)	0.011 (2)	−0.001 (2)

Geometric parameters (Å, º)

Cl—C24	1.734 (5)	C12—H12A	0.9800
O—C27	1.344 (6)	C13—C19	1.535 (6)
O—H0A	0.91 (6)	C13—C14	1.547 (7)
N—C21	1.254 (6)	C14—H14A	0.9600
N—C20	1.457 (5)	C14—H14B	0.9600
C1—C3	1.503 (9)	C14—H14C	0.9600
C1—H1A	0.9600	C15—C16	1.555 (7)
C1—H1B	0.9600	C15—H15A	0.9600
C1—H1C	0.9600	C15—H15B	0.9600
C2—C3	1.496 (8)	C15—H15C	0.9600
C2—H2A	0.9600	C16—C17	1.526 (6)
C2—H2B	0.9600	C16—C20	1.542 (6)
C2—H2C	0.9600	C17—C18	1.496 (6)
C3—C4	1.527 (7)	C17—H17A	0.9700
C3—H3A	0.9800	C17—H17B	0.9700
C4—C9	1.363 (6)	C18—C19	1.521 (6)
C4—C5	1.383 (7)	C18—H18A	0.9700
C5—C6	1.410 (6)	C18—H18B	0.9700
C5—H5A	0.9300	C19—H19A	0.9700
C6—C7	1.389 (6)	C19—H19B	0.9700
C6—C10	1.493 (6)	C20—H20A	0.9700
C7—C8	1.379 (6)	C20—H20B	0.9700
C7—C13	1.536 (6)	C21—C22	1.452 (6)
C8—C9	1.390 (7)	C21—H21A	0.9300
C8—H8A	0.9300	C22—C23	1.375 (6)
C9—H9A	0.9300	C22—C27	1.435 (7)
C10—C11	1.538 (7)	C23—C24	1.372 (6)
C10—H10A	0.9700	C23—H23A	0.9300
C10—H10B	0.9700	C24—C25	1.397 (9)
C11—C12	1.524 (6)	C25—C26	1.363 (7)
C11—H11A	0.9700	C25—H25A	0.9300
C11—H11B	0.9700	C26—C27	1.384 (6)
C12—C16	1.556 (6)	C26—H26A	0.9300
C12—C13	1.556 (6)
C27—O—H0A	112 (4)	C13—C14—H14B	109.5
C21—N—C20	121.6 (4)	H14A—C14—H14B	109.5
C3—C1—H1A	109.5	C13—C14—H14C	109.5
C3—C1—H1B	109.5	H14A—C14—H14C	109.5
H1A—C1—H1B	109.5	H14B—C14—H14C	109.5
C3—C1—H1C	109.5	C16—C15—H15A	109.5
H1A—C1—H1C	109.5	C16—C15—H15B	109.5
H1B—C1—H1C	109.5	H15A—C15—H15B	109.5
C3—C2—H2A	109.5	C16—C15—H15C	109.5
C3—C2—H2B	109.5	H15A—C15—H15C	109.5
H2A—C2—H2B	109.5	H15B—C15—H15C	109.5
C3—C2—H2C	109.5	C17—C16—C20	107.6 (4)
H2A—C2—H2C	109.5	C17—C16—C15	111.5 (4)
H2B—C2—H2C	109.5	C20—C16—C15	107.7 (4)
C2—C3—C1	113.2 (6)	C17—C16—C12	108.8 (4)
C2—C3—C4	112.4 (5)	C20—C16—C12	108.3 (3)
C1—C3—C4	112.7 (4)	C15—C16—C12	112.7 (4)
C2—C3—H3A	105.9	C18—C17—C16	114.8 (4)
C1—C3—H3A	105.9	C18—C17—H17A	108.6
C4—C3—H3A	105.9	C16—C17—H17A	108.6
C9—C4—C5	118.0 (4)	C18—C17—H17B	108.6
C9—C4—C3	120.8 (5)	C16—C17—H17B	108.6
C5—C4—C3	121.2 (5)	H17A—C17—H17B	107.5
C4—C5—C6	122.2 (4)	C17—C18—C19	111.9 (4)
C4—C5—H5A	118.9	C17—C18—H18A	109.2
C6—C5—H5A	118.9	C19—C18—H18A	109.2
C7—C6—C5	119.0 (4)	C17—C18—H18B	109.2
C7—C6—C10	122.4 (4)	C19—C18—H18B	109.2
C5—C6—C10	118.5 (4)	H18A—C18—H18B	107.9
C8—C7—C6	117.8 (4)	C18—C19—C13	113.0 (4)
C8—C7—C13	119.6 (4)	C18—C19—H19A	109.0
C6—C7—C13	122.4 (4)	C13—C19—H19A	109.0
C7—C8—C9	122.5 (4)	C18—C19—H19B	109.0
C7—C8—H8A	118.7	C13—C19—H19B	109.0
C9—C8—H8A	118.7	H19A—C19—H19B	107.8
C4—C9—C8	120.4 (5)	N—C20—C16	111.3 (4)
C4—C9—H9A	119.8	N—C20—H20A	109.4
C8—C9—H9A	119.8	C16—C20—H20A	109.4
C6—C10—C11	113.8 (4)	N—C20—H20B	109.4
C6—C10—H10A	108.8	C16—C20—H20B	109.4
C11—C10—H10A	108.8	H20A—C20—H20B	108.0
C6—C10—H10B	108.8	N—C21—C22	121.8 (5)
C11—C10—H10B	108.8	N—C21—H21A	119.1
H10A—C10—H10B	107.7	C22—C21—H21A	119.1
C12—C11—C10	109.0 (4)	C23—C22—C27	118.2 (4)
C12—C11—H11A	109.9	C23—C22—C21	121.8 (4)
C10—C11—H11A	109.9	C27—C22—C21	120.0 (4)
C12—C11—H11B	109.9	C24—C23—C22	121.8 (5)
C10—C11—H11B	109.9	C24—C23—H23A	119.1
H11A—C11—H11B	108.3	C22—C23—H23A	119.1
C11—C12—C16	115.4 (4)	C23—C24—C25	120.0 (5)
C11—C12—C13	110.0 (3)	C23—C24—Cl	120.9 (5)
C16—C12—C13	116.5 (3)	C25—C24—Cl	119.0 (4)
C11—C12—H12A	104.4	C26—C25—C24	119.4 (5)
C16—C12—H12A	104.4	C26—C25—H25A	120.3
C13—C12—H12A	104.4	C24—C25—H25A	120.3
C19—C13—C7	111.2 (4)	C25—C26—C27	121.8 (5)
C19—C13—C14	108.4 (4)	C25—C26—H26A	119.1
C7—C13—C14	105.8 (3)	C27—C26—H26A	119.1
C19—C13—C12	108.3 (3)	O—C27—C26	119.9 (5)
C7—C13—C12	108.5 (3)	O—C27—C22	121.3 (4)
C14—C13—C12	114.6 (4)	C26—C27—C22	118.8 (5)
C13—C14—H14A	109.5
C2—C3—C4—C9	116.2 (6)	C11—C12—C16—C17	−179.3 (4)
C1—C3—C4—C9	−114.4 (6)	C13—C12—C16—C17	49.3 (5)
C2—C3—C4—C5	−64.3 (7)	C11—C12—C16—C20	−62.6 (5)
C1—C3—C4—C5	65.1 (7)	C13—C12—C16—C20	166.1 (4)
C9—C4—C5—C6	−0.6 (8)	C11—C12—C16—C15	56.5 (6)
C3—C4—C5—C6	179.9 (5)	C13—C12—C16—C15	−74.8 (5)
C4—C5—C6—C7	0.7 (7)	C20—C16—C17—C18	−167.4 (4)
C4—C5—C6—C10	−178.9 (5)	C15—C16—C17—C18	74.7 (6)
C5—C6—C7—C8	−0.7 (7)	C12—C16—C17—C18	−50.2 (5)
C10—C6—C7—C8	178.8 (5)	C16—C17—C18—C19	55.2 (6)
C5—C6—C7—C13	−176.7 (4)	C17—C18—C19—C13	−56.5 (6)
C10—C6—C7—C13	2.8 (7)	C7—C13—C19—C18	172.0 (4)
C6—C7—C8—C9	0.7 (7)	C14—C13—C19—C18	−72.1 (5)
C13—C7—C8—C9	176.8 (4)	C12—C13—C19—C18	52.9 (5)
C5—C4—C9—C8	0.5 (7)	C21—N—C20—C16	131.3 (5)
C3—C4—C9—C8	−180.0 (5)	C17—C16—C20—N	−61.1 (5)
C7—C8—C9—C4	−0.6 (7)	C15—C16—C20—N	59.2 (5)
C7—C6—C10—C11	−13.3 (7)	C12—C16—C20—N	−178.6 (4)
C5—C6—C10—C11	166.2 (5)	C20—N—C21—C22	−177.8 (4)
C6—C10—C11—C12	44.2 (6)	N—C21—C22—C23	−176.2 (5)
C10—C11—C12—C16	159.2 (4)	N—C21—C22—C27	5.1 (7)
C10—C11—C12—C13	−66.5 (5)	C27—C22—C23—C24	1.8 (7)
C8—C7—C13—C19	42.1 (5)	C21—C22—C23—C24	−177.0 (5)
C6—C7—C13—C19	−142.0 (4)	C22—C23—C24—C25	−0.5 (7)
C8—C7—C13—C14	−75.4 (5)	C22—C23—C24—Cl	178.2 (4)
C6—C7—C13—C14	100.6 (5)	C23—C24—C25—C26	−0.3 (8)
C8—C7—C13—C12	161.2 (4)	Cl—C24—C25—C26	−179.0 (4)
C6—C7—C13—C12	−22.9 (6)	C24—C25—C26—C27	−0.3 (8)
C11—C12—C13—C19	175.1 (4)	C25—C26—C27—O	−178.9 (5)
C16—C12—C13—C19	−51.1 (5)	C25—C26—C27—C22	1.6 (7)
C11—C12—C13—C7	54.2 (5)	C23—C22—C27—O	178.2 (4)
C16—C12—C13—C7	−171.9 (4)	C21—C22—C27—O	−2.9 (7)
C11—C12—C13—C14	−63.8 (5)	C23—C22—C27—C26	−2.3 (7)
C16—C12—C13—C14	70.1 (5)	C21—C22—C27—C26	176.6 (4)