[4-(4-Meth­oxy­phen­yl)-8-oxo-3-(phenyl­selan­yl)spiro­[4.5]deca-3,6,9-trien-2-yl]methyl­cyanamide

The title compound, C₂₅H₂₂N₂O₂Se, crystallizes in the space group P2₁/c with one mol­ecule in the asymmetric unit. The compound was synthesized by the addition of phenyl­selenyl bromide to a cyanamide. The phenyl­selenyl portion and the cyano group, as well as the ketone functional group in the cyclo­hexa-2,5-dien-1-one portion of the structure, are disordered, with occupancy factors of 0.555 (14) and 0.445 (14).

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.041
• wR factor = 0.108
• Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2       ..N2       .       2.67 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12E     ..O2A      .       2.61 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H19A     ..SE1A     .       3.04 Ang.

Alert level G
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         16 Report
PLAT063_ALERT_4_G Crystal Size Possibly too Large for Beam Size ..       0.70 mm
PLAT177_ALERT_4_G The CIF-Embedded .res File Contains DELU Records          3 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          3 Report
PLAT230_ALERT_2_G Hirshfeld Test Diff for    N1       --C24      .        6.0 s.u.
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        27% Note
PLAT793_ALERT_4_G Model has Chirality at C2          (Centro SPGR)          S Verify
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............        222 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         15 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          5 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  12 ALERT level G = General information/check it is not something unexpected

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

---

Computing details

Data collection: APEX2 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

[4-(4-Methoxyphenyl)-8-oxo-3-(phenylselanyl)spiro[4.5]deca-3,6,9-trien-2-yl]methylcyanamide

Crystal data

C25H22N2O2Se	F(000) = 944
Mr = 461.40	Dx = 1.388 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.209 (7) Å	Cell parameters from 3960 reflections
b = 6.343 (3) Å	θ = 2.5–22.7°
c = 27.080 (14) Å	µ = 1.72 mm^−1
β = 103.356 (8)°	T = 296 K
V = 2207.4 (19) Å^3	Needle, colourless
Z = 4	0.70 × 0.18 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer	3448 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.047
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θmax = 28.3°, θmin = 2.5°
Tmin = 0.466, Tmax = 0.745	h = −17→17
22486 measured reflections	k = −8→8
5498 independent reflections	l = −35→36

Refinement

Refinement on F^2	222 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.108	w = 1/[σ^2(Fo^2) + (0.044P)^2 + 0.3647P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
5498 reflections	Δρmax = 0.34 e Å^−3
322 parameters	Δρmin = −0.38 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The H atoms were included in calculated positions and refined using a riding model, with C—H = 0.93, 0.96, 0.97, and 0.98 Å for aromatic, methyl, methylene, and terminal H atoms, respectively, and with U_iso(H) = 1.2U_eq(C) and 1.5U_eq(C-methyl).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Se1A	0.6308 (3)	0.4941 (10)	0.26771 (16)	0.0642 (7)	0.555 (14)
Se1B	0.6377 (4)	0.5228 (12)	0.2657 (2)	0.0694 (9)	0.445 (14)
O1	0.43190 (15)	1.1265 (3)	0.40821 (9)	0.0857 (6)
O2A	0.868 (2)	0.680 (5)	0.5648 (13)	0.090 (4)	0.555 (14)
O2B	0.884 (3)	0.623 (6)	0.5682 (15)	0.098 (6)	0.445 (14)
N1	0.90074 (14)	0.4281 (3)	0.31172 (8)	0.0486 (5)
N2	0.9080 (2)	0.8146 (4)	0.31572 (12)	0.0968 (10)
C1	0.72698 (16)	0.4392 (3)	0.32939 (9)	0.0433 (5)
C2	0.82397 (16)	0.3120 (3)	0.33276 (8)	0.0429 (5)
H2	0.806314	0.179735	0.314056	0.051*
C3	0.85901 (19)	0.2646 (4)	0.38949 (9)	0.0529 (6)
H3A	0.934144	0.274277	0.400499	0.063*
H3B	0.837873	0.123490	0.396611	0.063*
C4	0.80622 (18)	0.4317 (4)	0.41768 (9)	0.0482 (6)
C5	0.71565 (17)	0.5081 (3)	0.37431 (9)	0.0440 (5)
C6	0.63660 (17)	0.6620 (4)	0.38302 (8)	0.0459 (5)
C7	0.62917 (18)	0.8586 (4)	0.35983 (9)	0.0543 (6)
H7	0.672234	0.890191	0.338088	0.065*
C8	0.5593 (2)	1.0078 (4)	0.36838 (12)	0.0620 (7)
H8	0.554882	1.138108	0.352278	0.074*
C9	0.4961 (2)	0.9627 (4)	0.40089 (11)	0.0582 (7)
C10	0.49946 (19)	0.7697 (4)	0.42348 (9)	0.0602 (7)
H10	0.455269	0.739109	0.444734	0.072*
C11	0.56992 (19)	0.6186 (4)	0.41439 (9)	0.0555 (6)
H11	0.572089	0.486786	0.429638	0.067*
C12	0.3628 (3)	1.0895 (6)	0.44033 (13)	0.0939 (10)
H12D	0.313342	0.983074	0.425567	0.141*
H12E	0.326669	1.217622	0.444198	0.141*
H12F	0.401554	1.042867	0.472958	0.141*
C13	0.7701 (2)	0.3312 (4)	0.46039 (10)	0.0599 (7)
H13	0.728124	0.212131	0.453276	0.072*
C14	0.7940 (2)	0.4009 (5)	0.50789 (10)	0.0708 (8)
H14	0.769986	0.326985	0.532572	0.085*
C15	0.8565 (2)	0.5889 (6)	0.52255 (11)	0.0713 (8)
C16	0.8959 (2)	0.6902 (4)	0.48293 (10)	0.0628 (7)
H16	0.937462	0.809446	0.490864	0.075*
C17	0.87484 (18)	0.6182 (4)	0.43561 (9)	0.0532 (6)
H17	0.904369	0.687637	0.412135	0.064*
C18	0.6898 (7)	0.3385 (11)	0.2213 (4)	0.0502 (15)	0.555 (14)
C19	0.6434 (6)	0.1406 (12)	0.2145 (3)	0.0605 (15)	0.555 (14)
H19A	0.592557	0.104961	0.231710	0.073*	0.555 (14)
C20	0.6731 (7)	−0.0041 (8)	0.1819 (3)	0.0690 (16)	0.555 (14)
H20A	0.642134	−0.136467	0.177392	0.083*	0.555 (14)
C21	0.7492 (6)	0.0492 (13)	0.1562 (2)	0.0632 (17)	0.555 (14)
H21A	0.769056	−0.047586	0.134438	0.076*	0.555 (14)
C22	0.7955 (5)	0.2471 (15)	0.1630 (3)	0.0640 (16)	0.555 (14)
H22A	0.846402	0.282725	0.145803	0.077*	0.555 (14)
C23	0.7658 (7)	0.3917 (11)	0.1956 (3)	0.0584 (14)	0.555 (14)
H23A	0.796827	0.524156	0.200121	0.070*	0.555 (14)
C18A	0.6849 (10)	0.3222 (15)	0.2228 (5)	0.0531 (18)	0.445 (14)
C19A	0.6599 (8)	0.1141 (15)	0.2091 (4)	0.0598 (17)	0.445 (14)
H19B	0.612225	0.041799	0.223214	0.072*	0.445 (14)
C20A	0.7062 (8)	0.0142 (10)	0.1743 (4)	0.0644 (19)	0.445 (14)
H20B	0.689498	−0.125007	0.165074	0.077*	0.445 (14)
C21A	0.7775 (7)	0.1223 (17)	0.1532 (3)	0.0627 (19)	0.445 (14)
H21B	0.808463	0.055477	0.129846	0.075*	0.445 (14)
C22A	0.8025 (6)	0.3304 (18)	0.1669 (4)	0.0675 (18)	0.445 (14)
H22B	0.850157	0.402767	0.152757	0.081*	0.445 (14)
C23A	0.7562 (9)	0.4304 (12)	0.2017 (5)	0.0629 (18)	0.445 (14)
H23B	0.772885	0.569577	0.210896	0.076*	0.445 (14)
C24	0.9049 (2)	0.6355 (4)	0.31394 (10)	0.0572 (6)
C25	0.9865 (2)	0.3112 (4)	0.29936 (11)	0.0645 (7)
H25A	1.026422	0.403648	0.283148	0.097*
H25B	0.959357	0.197260	0.276855	0.097*
H25C	1.030196	0.255783	0.329927	0.097*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1A	0.0461 (8)	0.0904 (17)	0.0530 (12)	0.0220 (7)	0.0050 (6)	−0.0105 (10)
Se1B	0.081 (2)	0.0812 (14)	0.0464 (10)	0.0381 (14)	0.0162 (11)	0.0066 (9)
O1	0.0773 (14)	0.0701 (13)	0.1199 (17)	0.0161 (11)	0.0439 (13)	−0.0128 (12)
O2A	0.075 (7)	0.140 (10)	0.057 (4)	0.008 (5)	0.018 (4)	−0.023 (6)
O2B	0.072 (10)	0.170 (19)	0.055 (7)	−0.012 (11)	0.021 (7)	−0.039 (11)
N1	0.0476 (11)	0.0361 (10)	0.0676 (13)	0.0036 (8)	0.0250 (10)	−0.0006 (9)
N2	0.131 (2)	0.0393 (14)	0.149 (3)	−0.0025 (13)	0.092 (2)	0.0027 (15)
C1	0.0399 (12)	0.0427 (12)	0.0487 (13)	0.0004 (9)	0.0134 (10)	0.0010 (10)
C2	0.0422 (12)	0.0379 (12)	0.0502 (13)	0.0003 (9)	0.0142 (10)	0.0010 (10)
C3	0.0530 (14)	0.0495 (14)	0.0560 (14)	0.0052 (11)	0.0124 (11)	0.0039 (11)
C4	0.0495 (14)	0.0508 (13)	0.0455 (13)	−0.0051 (11)	0.0136 (10)	0.0041 (11)
C5	0.0399 (11)	0.0464 (13)	0.0482 (12)	−0.0028 (10)	0.0149 (10)	−0.0007 (11)
C6	0.0435 (13)	0.0499 (13)	0.0455 (12)	−0.0042 (10)	0.0125 (10)	−0.0078 (11)
C7	0.0504 (14)	0.0523 (15)	0.0638 (15)	−0.0046 (11)	0.0205 (12)	−0.0046 (12)
C8	0.0603 (16)	0.0481 (15)	0.0793 (19)	−0.0019 (12)	0.0196 (14)	−0.0024 (13)
C9	0.0516 (15)	0.0561 (16)	0.0687 (17)	−0.0022 (12)	0.0180 (13)	−0.0166 (13)
C10	0.0517 (15)	0.0740 (18)	0.0607 (16)	−0.0035 (13)	0.0248 (12)	−0.0078 (14)
C11	0.0563 (15)	0.0571 (15)	0.0568 (15)	−0.0006 (12)	0.0208 (12)	−0.0024 (12)
C12	0.072 (2)	0.116 (3)	0.101 (3)	0.024 (2)	0.0358 (19)	−0.025 (2)
C13	0.0585 (16)	0.0653 (16)	0.0566 (16)	−0.0089 (13)	0.0145 (12)	0.0097 (13)
C14	0.0679 (18)	0.099 (2)	0.0490 (16)	−0.0049 (17)	0.0210 (13)	0.0127 (16)
C15	0.0529 (16)	0.108 (2)	0.0532 (17)	0.0005 (16)	0.0122 (13)	−0.0099 (17)
C16	0.0529 (15)	0.0700 (17)	0.0645 (17)	−0.0075 (13)	0.0120 (12)	−0.0131 (14)
C17	0.0487 (14)	0.0558 (15)	0.0551 (15)	−0.0056 (11)	0.0119 (11)	0.0018 (12)
C18	0.045 (3)	0.064 (3)	0.041 (3)	0.008 (3)	0.009 (2)	0.003 (3)
C19	0.059 (3)	0.070 (3)	0.054 (3)	0.011 (3)	0.017 (2)	−0.004 (3)
C20	0.068 (4)	0.080 (3)	0.061 (3)	0.009 (3)	0.018 (3)	−0.009 (3)
C21	0.066 (4)	0.074 (4)	0.053 (3)	0.008 (3)	0.021 (3)	−0.006 (3)
C22	0.066 (3)	0.075 (4)	0.054 (3)	0.014 (3)	0.020 (2)	−0.011 (3)
C23	0.057 (3)	0.075 (3)	0.049 (3)	0.007 (3)	0.025 (2)	−0.003 (3)
C18A	0.051 (3)	0.063 (3)	0.044 (3)	0.010 (3)	0.009 (3)	−0.001 (3)
C19A	0.063 (3)	0.064 (3)	0.055 (3)	0.008 (3)	0.018 (3)	−0.007 (3)
C20A	0.070 (4)	0.071 (3)	0.055 (3)	0.010 (3)	0.021 (3)	−0.007 (3)
C21A	0.066 (4)	0.070 (4)	0.054 (3)	0.009 (3)	0.018 (3)	−0.008 (3)
C22A	0.073 (3)	0.076 (4)	0.057 (3)	0.008 (3)	0.020 (3)	−0.009 (4)
C23A	0.062 (3)	0.076 (3)	0.054 (3)	0.014 (3)	0.019 (3)	−0.008 (3)
C24	0.0641 (16)	0.0477 (16)	0.0697 (17)	0.0007 (12)	0.0362 (13)	0.0036 (12)
C25	0.0585 (16)	0.0543 (15)	0.091 (2)	0.0049 (12)	0.0378 (14)	−0.0049 (14)

Geometric parameters (Å, º)

Se1A—C1	1.883 (4)	C12—H12F	0.9600
Se1A—C18	1.901 (6)	C13—C14	1.328 (4)
Se1B—C18A	1.921 (9)	C13—H13	0.9300
Se1B—C1	1.926 (5)	C14—C15	1.452 (4)
O1—C9	1.384 (3)	C14—H14	0.9300
O1—C12	1.418 (4)	C15—C16	1.447 (4)
O2A—C15	1.26 (3)	C16—C17	1.328 (3)
O2B—C15	1.22 (4)	C16—H16	0.9300
N1—C24	1.318 (3)	C17—H17	0.9300
N1—C25	1.456 (3)	C18—C19	1.3900
N1—C2	1.470 (3)	C18—C23	1.3900
N2—C24	1.137 (3)	C19—C20	1.3900
C1—C5	1.333 (3)	C19—H19A	0.9300
C1—C2	1.499 (3)	C20—C21	1.3900
C2—C3	1.528 (3)	C20—H20A	0.9300
C2—H2	0.9800	C21—C22	1.3900
C3—C4	1.562 (3)	C21—H21A	0.9300
C3—H3A	0.9700	C22—C23	1.3900
C3—H3B	0.9700	C22—H22A	0.9300
C4—C13	1.492 (3)	C23—H23A	0.9300
C4—C17	1.501 (3)	C18A—C19A	1.3900
C4—C5	1.548 (3)	C18A—C23A	1.3900
C5—C6	1.488 (3)	C19A—C20A	1.3900
C6—C11	1.385 (3)	C19A—H19B	0.9300
C6—C7	1.389 (3)	C20A—C21A	1.3900
C7—C8	1.378 (3)	C20A—H20B	0.9300
C7—H7	0.9300	C21A—C22A	1.3900
C8—C9	1.376 (4)	C21A—H21B	0.9300
C8—H8	0.9300	C22A—C23A	1.3900
C9—C10	1.364 (4)	C22A—H22B	0.9300
C10—C11	1.397 (3)	C23A—H23B	0.9300
C10—H10	0.9300	C25—H25A	0.9600
C11—H11	0.9300	C25—H25B	0.9600
C12—H12D	0.9600	C25—H25C	0.9600
C12—H12E	0.9600
C1—Se1A—C18	101.2 (4)	C4—C13—H13	117.9
C18A—Se1B—C1	98.1 (5)	C13—C14—C15	122.1 (3)
C9—O1—C12	117.8 (2)	C13—C14—H14	119.0
C24—N1—C25	119.50 (19)	C15—C14—H14	119.0
C24—N1—C2	120.49 (18)	O2B—C15—C16	127 (2)
C25—N1—C2	118.50 (18)	O2A—C15—C16	118.7 (17)
C5—C1—C2	113.3 (2)	O2B—C15—C14	116 (2)
C5—C1—Se1A	123.6 (2)	O2A—C15—C14	124.6 (17)
C2—C1—Se1A	123.1 (2)	C16—C15—C14	116.2 (2)
C5—C1—Se1B	123.5 (3)	C17—C16—C15	122.1 (3)
C2—C1—Se1B	122.7 (2)	C17—C16—H16	118.9
N1—C2—C1	111.31 (17)	C15—C16—H16	118.9
N1—C2—C3	114.34 (18)	C16—C17—C4	124.0 (2)
C1—C2—C3	102.90 (17)	C16—C17—H17	118.0
N1—C2—H2	109.4	C4—C17—H17	118.0
C1—C2—H2	109.4	C19—C18—C23	120.0
C3—C2—H2	109.4	C19—C18—Se1A	108.8 (5)
C2—C3—C4	106.98 (18)	C23—C18—Se1A	131.2 (5)
C2—C3—H3A	110.3	C20—C19—C18	120.0
C4—C3—H3A	110.3	C20—C19—H19A	120.0
C2—C3—H3B	110.3	C18—C19—H19A	120.0
C4—C3—H3B	110.3	C19—C20—C21	120.0
H3A—C3—H3B	108.6	C19—C20—H20A	120.0
C13—C4—C17	111.3 (2)	C21—C20—H20A	120.0
C13—C4—C5	113.1 (2)	C20—C21—C22	120.0
C17—C4—C5	107.56 (19)	C20—C21—H21A	120.0
C13—C4—C3	110.4 (2)	C22—C21—H21A	120.0
C17—C4—C3	112.87 (19)	C23—C22—C21	120.0
C5—C4—C3	101.28 (18)	C23—C22—H22A	120.0
C1—C5—C6	126.2 (2)	C21—C22—H22A	120.0
C1—C5—C4	111.1 (2)	C22—C23—C18	120.0
C6—C5—C4	122.2 (2)	C22—C23—H23A	120.0
C11—C6—C7	117.8 (2)	C18—C23—H23A	120.0
C11—C6—C5	122.4 (2)	C19A—C18A—C23A	120.0
C7—C6—C5	119.7 (2)	C19A—C18A—Se1B	134.5 (7)
C8—C7—C6	121.3 (2)	C23A—C18A—Se1B	105.5 (7)
C8—C7—H7	119.3	C20A—C19A—C18A	120.0
C6—C7—H7	119.3	C20A—C19A—H19B	120.0
C9—C8—C7	119.6 (2)	C18A—C19A—H19B	120.0
C9—C8—H8	120.2	C21A—C20A—C19A	120.0
C7—C8—H8	120.2	C21A—C20A—H20B	120.0
C10—C9—C8	120.8 (2)	C19A—C20A—H20B	120.0
C10—C9—O1	124.5 (2)	C20A—C21A—C22A	120.0
C8—C9—O1	114.7 (2)	C20A—C21A—H21B	120.0
C9—C10—C11	119.4 (2)	C22A—C21A—H21B	120.0
C9—C10—H10	120.3	C21A—C22A—C23A	120.0
C11—C10—H10	120.3	C21A—C22A—H22B	120.0
C6—C11—C10	121.0 (2)	C23A—C22A—H22B	120.0
C6—C11—H11	119.5	C22A—C23A—C18A	120.0
C10—C11—H11	119.5	C22A—C23A—H23B	120.0
O1—C12—H12D	109.5	C18A—C23A—H23B	120.0
O1—C12—H12E	109.5	N2—C24—N1	179.7 (4)
H12D—C12—H12E	109.5	N1—C25—H25A	109.5
O1—C12—H12F	109.5	N1—C25—H25B	109.5
H12D—C12—H12F	109.5	H25A—C25—H25B	109.5
H12E—C12—H12F	109.5	N1—C25—H25C	109.5
C14—C13—C4	124.2 (3)	H25A—C25—H25C	109.5
C14—C13—H13	117.9	H25B—C25—H25C	109.5
C18—Se1A—C1—C5	−176.5 (3)	C12—O1—C9—C10	−1.8 (4)
C18—Se1A—C1—C2	3.1 (5)	C12—O1—C9—C8	178.5 (3)
C24—N1—C2—C1	30.3 (3)	C8—C9—C10—C11	1.6 (4)
C25—N1—C2—C1	−163.8 (2)	O1—C9—C10—C11	−178.0 (2)
C24—N1—C2—C3	−85.8 (3)	C7—C6—C11—C10	−1.7 (4)
C25—N1—C2—C3	80.2 (3)	C5—C6—C11—C10	177.3 (2)
C5—C1—C2—N1	−109.0 (2)	C9—C10—C11—C6	0.3 (4)
Se1A—C1—C2—N1	71.3 (3)	C17—C4—C13—C14	1.3 (4)
Se1B—C1—C2—N1	63.7 (4)	C5—C4—C13—C14	−119.9 (3)
C5—C1—C2—C3	13.9 (2)	C3—C4—C13—C14	127.4 (3)
Se1A—C1—C2—C3	−165.8 (3)	C4—C13—C14—C15	1.8 (5)
Se1B—C1—C2—C3	−173.4 (3)	C13—C14—C15—O2B	−171.4 (16)
N1—C2—C3—C4	100.3 (2)	C13—C14—C15—O2A	168.6 (13)
C1—C2—C3—C4	−20.6 (2)	C13—C14—C15—C16	−3.2 (4)
C2—C3—C4—C13	139.8 (2)	O2B—C15—C16—C17	168.1 (17)
C2—C3—C4—C17	−95.0 (2)	O2A—C15—C16—C17	−171.0 (13)
C2—C3—C4—C5	19.7 (2)	C14—C15—C16—C17	1.3 (4)
C2—C1—C5—C6	170.7 (2)	C15—C16—C17—C4	2.0 (4)
Se1A—C1—C5—C6	−9.6 (4)	C13—C4—C17—C16	−3.2 (3)
Se1B—C1—C5—C6	−1.9 (4)	C5—C4—C17—C16	121.2 (3)
C2—C1—C5—C4	−1.2 (3)	C3—C4—C17—C16	−128.0 (3)
Se1A—C1—C5—C4	178.5 (3)	C23—C18—C19—C20	0.0
Se1B—C1—C5—C4	−173.9 (3)	Se1A—C18—C19—C20	179.8 (7)
C13—C4—C5—C1	−129.8 (2)	C18—C19—C20—C21	0.0
C17—C4—C5—C1	106.9 (2)	C19—C20—C21—C22	0.0
C3—C4—C5—C1	−11.7 (2)	C20—C21—C22—C23	0.0
C13—C4—C5—C6	57.9 (3)	C21—C22—C23—C18	0.0
C17—C4—C5—C6	−65.4 (3)	C19—C18—C23—C22	0.0
C3—C4—C5—C6	175.99 (19)	Se1A—C18—C23—C22	−179.8 (8)
C1—C5—C6—C11	125.9 (3)	C23A—C18A—C19A—C20A	0.0
C4—C5—C6—C11	−63.1 (3)	Se1B—C18A—C19A—C20A	176.7 (11)
C1—C5—C6—C7	−55.1 (3)	C18A—C19A—C20A—C21A	0.0
C4—C5—C6—C7	115.9 (2)	C19A—C20A—C21A—C22A	0.0
C11—C6—C7—C8	1.2 (4)	C20A—C21A—C22A—C23A	0.0
C5—C6—C7—C8	−177.8 (2)	C21A—C22A—C23A—C18A	0.0
C6—C7—C8—C9	0.6 (4)	C19A—C18A—C23A—C22A	0.0
C7—C8—C9—C10	−2.1 (4)	Se1B—C18A—C23A—C22A	−177.6 (8)
C7—C8—C9—O1	177.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N2^i	0.98	2.67	3.411 (4)	132
C3—H3A···O2A^ii	0.97	2.58	3.55 (3)	176
C3—H3A···O2B^ii	0.97	2.44	3.40 (4)	168
C12—H12E···O2A^iii	0.96	2.61	3.36 (3)	135
C19—H19A···Se1A^iv	0.93	3.04	3.876 (8)	151

Symmetry codes: (i) x, y−1, z; (ii) −x+2, −y+1, −z+1; (iii) −x+1, −y+2, −z+1; (iv) −x+1, y−1/2, −z+1/2.