4-Cyano-3-fluoro­phenyl (2E)-3-(3-meth­oxy-4-octyloxyphen­yl)acrylate

In the title compound, C₂₅H₂₈NO₄F, the two aromatic rings are almost perpendicular with a dihedral angle of 84.6 (1)°. Mol­ecules are linked into dimers by C—H...O inter­actions. The packing is further stabilized by π–π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in main residue
• R factor = 0.064
• wR factor = 0.198
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found





Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.11 Ratio

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.35 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C7
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C8
PLAT301_ALERT_3_C Main Residue  Disorder .........................       3.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C1     -   C2     ...       1.44 Ang.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      53.00 A   3  
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          1
            N1  -C1  -C2  -C3     12.00 12.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          2
            N1  -C1  -C2  -C7   -170.00 12.00   1.555   1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      15.40 Deg.
              C3   -F1A  -H3A     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      17.20 Deg.
              C7   -F1B  -H7A     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       6.70 Deg.
              F1A  -C3   -H3A     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       6.70 Deg.
              F1B  -C7   -H7A     1.555   1.555   1.555

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  10 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   3 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).

4-Cyano-3-fluorophenyl (2E)-3-(3-methoxy-4-octyloxyphenyl)acrylate

Crystal data

C25H28FNO4	Z = 2
Mr = 425.48	F(000) = 452
Triclinic, P1	Dx = 1.198 Mg m^−3
a = 7.873 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.279 (6) Å	Cell parameters from 1223 reflections
c = 14.048 (7) Å	θ = 2.2–21.9°
α = 81.016 (11)°	µ = 0.09 mm^−1
β = 80.419 (10)°	T = 293 K
γ = 74.95 (1)°	Prism, colourless
V = 1179.5 (10) Å^3	0.19 × 0.14 × 0.09 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	4528 independent reflections
Radiation source: fine-focus sealed tube	2364 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
Detector resolution: 8.33 pixels mm^-1	θmax = 26.2°, θmin = 1.9°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→5
Tmin = 0.984, Tmax = 0.992	l = −17→15
6504 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) = 0.198	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0887P)^2 + 0.167P] where P = (Fo^2 + 2Fc^2)/3
4528 reflections	(Δ/σ)max < 0.001
290 parameters	Δρmax = 0.33 e Å^−3
0 restraints	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	Occ. (<1)
F1A	1.3202 (4)	0.0716 (3)	−0.0143 (3)	0.1146 (15)	0.660 (5)
F1B	1.1580 (12)	−0.2940 (8)	0.0364 (6)	0.150 (4)	0.340 (5)
O1	0.9005 (2)	−0.0064 (2)	0.25491 (14)	0.0828 (7)
O2	1.1027 (3)	−0.0455 (2)	0.35565 (14)	0.0892 (8)
O3	0.0383 (2)	0.32809 (18)	0.62596 (13)	0.0638 (6)
O4	0.3270 (2)	0.23669 (18)	0.70227 (13)	0.0651 (6)
N1	1.4609 (5)	−0.1779 (4)	−0.1401 (2)	0.1277 (14)
C1	1.3688 (5)	−0.1532 (4)	−0.0711 (2)	0.0883 (11)
C2	1.2547 (4)	−0.1185 (4)	0.0161 (2)	0.0701 (9)
C3	1.2366 (4)	−0.0053 (4)	0.0450 (2)	0.0794 (10)
H3A	1.3025	0.0490	0.0094	0.095*	0.34
C4	1.1257 (4)	0.0315 (3)	0.1260 (3)	0.0827 (10)
H4A	1.1166	0.1083	0.1454	0.099*
C5	1.0272 (4)	−0.0475 (3)	0.1786 (2)	0.0671 (9)
C6	1.0417 (4)	−0.1611 (3)	0.1532 (2)	0.0800 (10)
H6A	0.9768	−0.2143	0.1901	0.096*
C7	1.1549 (5)	−0.1955 (4)	0.0713 (2)	0.0831 (10)
H7A	1.1654	−0.2723	0.0514	0.100*	0.66
C8	0.9521 (4)	−0.0033 (3)	0.34181 (19)	0.0594 (7)
C9	0.8059 (3)	0.0517 (3)	0.41088 (19)	0.0581 (7)
H9A	0.8272	0.0520	0.4740	0.070*
C10	0.6432 (3)	0.1018 (2)	0.38867 (19)	0.0552 (7)
H10A	0.6272	0.1002	0.3248	0.066*
C11	0.4869 (3)	0.1588 (2)	0.45123 (18)	0.0515 (7)
C12	0.4896 (3)	0.1689 (2)	0.54954 (18)	0.0518 (7)
H12A	0.5947	0.1379	0.5766	0.062*
C13	0.3384 (3)	0.2240 (2)	0.60570 (18)	0.0507 (7)
C14	0.1793 (3)	0.2735 (2)	0.56482 (19)	0.0526 (7)
C15	0.1761 (3)	0.2620 (3)	0.4693 (2)	0.0613 (8)
H15A	0.0710	0.2925	0.4421	0.074*
C16	0.3285 (3)	0.2052 (3)	0.4134 (2)	0.0618 (8)
H16A	0.3243	0.1980	0.3489	0.074*
C17	−0.1286 (3)	0.3756 (3)	0.5886 (2)	0.0610 (8)
H17A	−0.1675	0.3089	0.5695	0.073*
H17B	−0.1164	0.4358	0.5321	0.073*
C18	−0.2605 (3)	0.4349 (3)	0.6671 (2)	0.0638 (8)
H18A	−0.2193	0.5006	0.6860	0.077*
H18B	−0.2697	0.3741	0.7235	0.077*
C19	−0.4427 (3)	0.4879 (3)	0.6347 (2)	0.0638 (8)
H19A	−0.4350	0.5536	0.5818	0.077*
H19B	−0.4786	0.4237	0.6100	0.077*
C20	−0.5832 (4)	0.5386 (3)	0.7156 (2)	0.0729 (9)
H20A	−0.5917	0.4730	0.7684	0.087*
H20B	−0.5475	0.6028	0.7404	0.087*
C21	−0.7641 (4)	0.5917 (3)	0.6821 (2)	0.0784 (9)
H21A	−0.7541	0.6562	0.6285	0.094*
H21B	−0.7991	0.5270	0.6576	0.094*
C22	−0.9084 (4)	0.6447 (4)	0.7595 (3)	0.1020 (13)
H22A	−1.0110	0.6920	0.7290	0.122*
H22B	−0.8671	0.7011	0.7905	0.122*
C23	−0.9646 (6)	0.5472 (5)	0.8368 (3)	0.149 (2)
H23A	−0.9779	0.4802	0.8052	0.179*
H23B	−0.8709	0.5136	0.8775	0.179*
C24	−1.1334 (6)	0.5939 (5)	0.8999 (4)	0.170 (2)
H24A	−1.1613	0.5274	0.9464	0.255*
H24B	−1.2275	0.6263	0.8605	0.255*
H24C	−1.1201	0.6581	0.9336	0.255*
C25	0.4729 (4)	0.1706 (3)	0.7514 (2)	0.0792 (10)
H25A	0.4497	0.1875	0.8178	0.119*
H25B	0.5780	0.1960	0.7202	0.119*
H25C	0.4898	0.0836	0.7494	0.119*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1A	0.101 (2)	0.125 (3)	0.112 (3)	−0.040 (2)	0.0229 (19)	−0.013 (2)
F1B	0.200 (8)	0.122 (6)	0.137 (6)	−0.067 (6)	0.062 (6)	−0.083 (5)
O1	0.0498 (11)	0.1267 (19)	0.0593 (12)	0.0091 (12)	0.0008 (9)	−0.0336 (13)
O2	0.0487 (12)	0.139 (2)	0.0660 (13)	0.0109 (12)	−0.0077 (10)	−0.0290 (13)
O3	0.0422 (10)	0.0769 (13)	0.0643 (12)	0.0010 (9)	−0.0005 (8)	−0.0177 (10)
O4	0.0488 (10)	0.0875 (14)	0.0523 (11)	−0.0038 (10)	−0.0006 (8)	−0.0165 (10)
N1	0.108 (2)	0.180 (4)	0.075 (2)	0.000 (2)	0.0164 (19)	−0.042 (2)
C1	0.074 (2)	0.119 (3)	0.060 (2)	−0.002 (2)	−0.0002 (17)	−0.023 (2)
C2	0.0558 (17)	0.092 (3)	0.0523 (17)	0.0035 (17)	−0.0038 (14)	−0.0169 (18)
C3	0.0643 (19)	0.090 (3)	0.074 (2)	−0.0139 (19)	0.0081 (16)	−0.007 (2)
C4	0.067 (2)	0.082 (2)	0.093 (2)	−0.0017 (18)	0.0043 (18)	−0.035 (2)
C5	0.0470 (15)	0.089 (2)	0.0538 (17)	0.0056 (16)	−0.0051 (13)	−0.0130 (17)
C6	0.080 (2)	0.084 (2)	0.064 (2)	−0.0087 (19)	0.0060 (16)	−0.0062 (19)
C7	0.087 (2)	0.087 (3)	0.068 (2)	−0.009 (2)	0.0055 (18)	−0.027 (2)
C8	0.0484 (15)	0.0705 (19)	0.0512 (16)	−0.0016 (14)	−0.0027 (12)	−0.0089 (14)
C9	0.0511 (15)	0.0658 (18)	0.0526 (16)	−0.0054 (13)	−0.0020 (12)	−0.0124 (14)
C10	0.0502 (15)	0.0586 (17)	0.0513 (15)	−0.0060 (13)	0.0007 (12)	−0.0097 (13)
C11	0.0468 (14)	0.0513 (16)	0.0518 (15)	−0.0061 (12)	−0.0017 (11)	−0.0073 (13)
C12	0.0398 (13)	0.0552 (16)	0.0564 (16)	−0.0053 (12)	−0.0041 (11)	−0.0070 (13)
C13	0.0485 (14)	0.0525 (16)	0.0478 (15)	−0.0097 (12)	0.0005 (11)	−0.0077 (12)
C14	0.0416 (13)	0.0556 (17)	0.0549 (16)	−0.0045 (12)	0.0013 (12)	−0.0100 (13)
C15	0.0437 (14)	0.070 (2)	0.0617 (18)	0.0017 (13)	−0.0065 (12)	−0.0103 (15)
C16	0.0532 (16)	0.0712 (19)	0.0555 (16)	−0.0028 (14)	−0.0065 (13)	−0.0119 (15)
C17	0.0423 (14)	0.0678 (19)	0.0677 (18)	−0.0019 (13)	−0.0054 (12)	−0.0137 (15)
C18	0.0501 (15)	0.0670 (19)	0.0682 (18)	−0.0033 (14)	−0.0020 (13)	−0.0140 (15)
C19	0.0484 (15)	0.0625 (18)	0.0738 (19)	−0.0007 (13)	−0.0042 (14)	−0.0138 (15)
C20	0.0517 (16)	0.081 (2)	0.079 (2)	0.0009 (15)	−0.0036 (15)	−0.0211 (18)
C21	0.0553 (17)	0.081 (2)	0.090 (2)	0.0037 (16)	−0.0058 (16)	−0.0211 (19)
C22	0.067 (2)	0.122 (3)	0.095 (3)	0.015 (2)	−0.0023 (19)	−0.019 (2)
C23	0.105 (3)	0.201 (5)	0.087 (3)	0.031 (3)	0.017 (2)	−0.006 (3)
C24	0.111 (4)	0.215 (6)	0.149 (5)	−0.009 (4)	0.008 (3)	0.007 (4)
C25	0.0642 (19)	0.104 (3)	0.0608 (18)	−0.0030 (18)	−0.0129 (15)	−0.0087 (18)

Geometric parameters (Å, º)

F1A—C3	1.330 (4)	C13—C14	1.410 (3)
F1A—H3A	0.4139	C14—C15	1.373 (4)
F1B—C7	1.276 (7)	C15—C16	1.383 (4)
F1B—H7A	0.3672	C15—H15A	0.9300
O1—C8	1.357 (3)	C16—H16A	0.9300
O1—C5	1.385 (3)	C17—C18	1.493 (4)
O2—C8	1.194 (3)	C17—H17A	0.9700
O3—C14	1.357 (3)	C17—H17B	0.9700
O3—C17	1.437 (3)	C18—C19	1.519 (4)
O4—C13	1.372 (3)	C18—H18A	0.9700
O4—C25	1.418 (3)	C18—H18B	0.9700
N1—C1	1.135 (4)	C19—C20	1.517 (4)
C1—C2	1.436 (4)	C19—H19A	0.9700
C2—C3	1.365 (5)	C19—H19B	0.9700
C2—C7	1.383 (5)	C20—C21	1.517 (4)
C3—C4	1.362 (5)	C20—H20A	0.9700
C3—H3A	0.9370	C20—H20B	0.9700
C4—C5	1.380 (5)	C21—C22	1.507 (4)
C4—H4A	0.9300	C21—H21A	0.9700
C5—C6	1.354 (5)	C21—H21B	0.9700
C6—C7	1.373 (4)	C22—C23	1.517 (6)
C6—H6A	0.9300	C22—H22A	0.9700
C7—H7A	0.9313	C22—H22B	0.9700
C8—C9	1.448 (4)	C23—C24	1.490 (5)
C9—C10	1.327 (3)	C23—H23A	0.9700
C9—H9A	0.9300	C23—H23B	0.9700
C10—C11	1.451 (3)	C24—H24A	0.9600
C10—H10A	0.9300	C24—H24B	0.9600
C11—C16	1.380 (3)	C24—H24C	0.9600
C11—C12	1.407 (4)	C25—H25A	0.9600
C12—C13	1.372 (3)	C25—H25B	0.9600
C12—H12A	0.9300	C25—H25C	0.9600
C3—F1A—H3A	15.4	C15—C16—H16A	119.2
C7—F1B—H7A	17.2	O3—C17—C18	107.9 (2)
C8—O1—C5	119.4 (2)	O3—C17—H17A	110.1
C14—O3—C17	117.6 (2)	C18—C17—H17A	110.1
C13—O4—C25	117.3 (2)	O3—C17—H17B	110.1
N1—C1—C2	178.1 (5)	C18—C17—H17B	110.1
C3—C2—C7	117.8 (3)	H17A—C17—H17B	108.4
C3—C2—C1	120.4 (3)	C17—C18—C19	112.0 (2)
C7—C2—C1	121.7 (4)	C17—C18—H18A	109.2
F1A—C3—C4	121.3 (4)	C19—C18—H18A	109.2
F1A—C3—C2	116.7 (3)	C17—C18—H18B	109.2
C4—C3—C2	121.8 (4)	C19—C18—H18B	109.2
F1A—C3—H3A	6.7	H18A—C18—H18B	107.9
C4—C3—H3A	118.2	C20—C19—C18	113.1 (2)
C2—C3—H3A	120.0	C20—C19—H19A	109.0
C3—C4—C5	118.6 (4)	C18—C19—H19A	109.0
C3—C4—H4A	120.7	C20—C19—H19B	109.0
C5—C4—H4A	120.7	C18—C19—H19B	109.0
C6—C5—C4	121.7 (3)	H19A—C19—H19B	107.8
C6—C5—O1	118.9 (3)	C21—C20—C19	112.5 (3)
C4—C5—O1	119.2 (3)	C21—C20—H20A	109.1
C5—C6—C7	118.2 (4)	C19—C20—H20A	109.1
C5—C6—H6A	120.9	C21—C20—H20B	109.1
C7—C6—H6A	120.9	C19—C20—H20B	109.1
F1B—C7—C6	121.3 (5)	H20A—C20—H20B	107.8
F1B—C7—C2	116.4 (4)	C22—C21—C20	114.7 (3)
C6—C7—C2	121.8 (4)	C22—C21—H21A	108.6
F1B—C7—H7A	6.7	C20—C21—H21A	108.6
C6—C7—H7A	120.0	C22—C21—H21B	108.6
C2—C7—H7A	118.2	C20—C21—H21B	108.6
O2—C8—O1	120.7 (2)	H21A—C21—H21B	107.6
O2—C8—C9	126.9 (3)	C21—C22—C23	113.5 (3)
O1—C8—C9	112.4 (2)	C21—C22—H22A	108.9
C10—C9—C8	123.3 (3)	C23—C22—H22A	108.9
C10—C9—H9A	118.3	C21—C22—H22B	108.9
C8—C9—H9A	118.3	C23—C22—H22B	108.9
C9—C10—C11	128.3 (3)	H22A—C22—H22B	107.7
C9—C10—H10A	115.8	C24—C23—C22	114.1 (4)
C11—C10—H10A	115.8	C24—C23—H23A	108.7
C16—C11—C12	118.3 (2)	C22—C23—H23A	108.7
C16—C11—C10	119.1 (2)	C24—C23—H23B	108.7
C12—C11—C10	122.7 (2)	C22—C23—H23B	108.7
C13—C12—C11	120.5 (2)	H23A—C23—H23B	107.6
C13—C12—H12A	119.7	C23—C24—H24A	109.5
C11—C12—H12A	119.7	C23—C24—H24B	109.5
C12—C13—O4	124.9 (2)	H24A—C24—H24B	109.5
C12—C13—C14	120.2 (2)	C23—C24—H24C	109.5
O4—C13—C14	114.9 (2)	H24A—C24—H24C	109.5
O3—C14—C15	125.2 (2)	H24B—C24—H24C	109.5
O3—C14—C13	115.6 (2)	O4—C25—H25A	109.5
C15—C14—C13	119.2 (2)	O4—C25—H25B	109.5
C14—C15—C16	120.2 (2)	H25A—C25—H25B	109.5
C14—C15—H15A	119.9	O4—C25—H25C	109.5
C16—C15—H15A	119.9	H25A—C25—H25C	109.5
C11—C16—C15	121.6 (3)	H25B—C25—H25C	109.5
C11—C16—H16A	119.2
N1—C1—C2—C3	12 (12)	C9—C10—C11—C12	0.3 (5)
N1—C1—C2—C7	−170 (12)	C16—C11—C12—C13	−0.3 (4)
C7—C2—C3—F1A	−173.6 (3)	C10—C11—C12—C13	179.8 (3)
C1—C2—C3—F1A	4.0 (5)	C11—C12—C13—O4	179.1 (2)
C7—C2—C3—C4	0.7 (5)	C11—C12—C13—C14	−1.4 (4)
C1—C2—C3—C4	178.2 (3)	C25—O4—C13—C12	−11.0 (4)
F1A—C3—C4—C5	172.7 (3)	C25—O4—C13—C14	169.4 (2)
C2—C3—C4—C5	−1.3 (5)	C17—O3—C14—C15	1.2 (4)
C3—C4—C5—C6	1.8 (5)	C17—O3—C14—C13	−177.6 (2)
C3—C4—C5—O1	−173.3 (3)	C12—C13—C14—O3	−178.8 (2)
C8—O1—C5—C6	105.7 (3)	O4—C13—C14—O3	0.8 (4)
C8—O1—C5—C4	−79.1 (4)	C12—C13—C14—C15	2.4 (4)
C4—C5—C6—C7	−1.6 (5)	O4—C13—C14—C15	−178.1 (2)
O1—C5—C6—C7	173.4 (3)	O3—C14—C15—C16	179.6 (3)
C5—C6—C7—F1B	−170.9 (6)	C13—C14—C15—C16	−1.7 (4)
C5—C6—C7—C2	1.0 (5)	C12—C11—C16—C15	1.0 (4)
C3—C2—C7—F1B	171.8 (6)	C10—C11—C16—C15	−179.1 (3)
C1—C2—C7—F1B	−5.8 (7)	C14—C15—C16—C11	0.0 (5)
C3—C2—C7—C6	−0.5 (5)	C14—O3—C17—C18	−177.9 (2)
C1—C2—C7—C6	−178.0 (3)	O3—C17—C18—C19	−179.8 (2)
C5—O1—C8—O2	−6.5 (5)	C17—C18—C19—C20	174.9 (3)
C5—O1—C8—C9	175.0 (3)	C18—C19—C20—C21	179.8 (3)
O2—C8—C9—C10	176.8 (3)	C19—C20—C21—C22	−179.4 (3)
O1—C8—C9—C10	−4.8 (4)	C20—C21—C22—C23	−71.0 (5)
C8—C9—C10—C11	179.7 (3)	C21—C22—C23—C24	−166.3 (4)
C9—C10—C11—C16	−179.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O2^i	0.93	2.53	3.459 (4)	177
C10—H10A···O1	0.93	2.31	2.700 (3)	104

Symmetry code: (i) −x+2, −y, −z+1.