Crystal structure of 2′-[(2′,4′-di­fluoro­biphenyl-4-yl)carbon­yl]-1′-phenyl-1′,2′,5′,6′,7′,7a'-hexa­hydro­spiro­[indole-3,3′-pyrrolizin]-2(1H)-one

In the title spiro-pyrrolizidine derivative, the di­fluoro­phenyl group is oriented at an angle of 54.3 (1)° with respect to the oxindole moiety. In the crystal, mol­ecules are linked via N—H...O hydrogen bonds, forming dimers with an (8) motif.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.057
• wR factor = 0.155
• Data-to-parameter ratio = 17.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      7.445 Check

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          4 Note
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          1 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT230_ALERT_2_G Hirshfeld Test Diff for    C17    --  C18'    ..        7.0 su
PLAT230_ALERT_2_G Hirshfeld Test Diff for    C19    --  C18     ..        6.5 su
PLAT301_ALERT_3_G Main Residue  Disorder ............ Percentage =          3 Note
PLAT793_ALERT_4_G The Model has Chirality at C14     (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C15     (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C20     (Centro SPGR)          R Verify
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          4 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        182 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 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
   6 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

2'-[(2',4'-Difluorobiphenyl-4-yl)carbonyl]-1'-phenyl-1',2',5',6',7',7a'-hexahydrospiro[indole-3,3'-pyrrolizin]-2(1H)-one

Crystal data

C33H26F2N2O2	Dx = 1.329 Mg m^−3
Mr = 520.56	Melting point: 451 K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.6019 (13) Å	Cell parameters from 18178 reflections
b = 9.3128 (10) Å	θ = 2.2–27.2°
c = 22.441 (2) Å	µ = 0.09 mm^−1
β = 98.805 (2)°	T = 292 K
V = 2602.6 (5) Å^3	Block, brown
Z = 4	0.22 × 0.20 × 0.18 mm
F(000) = 1088

Data collection

Bruker SMART APEX CCD area-detector diffractometer	Rint = 0.025
Radiation source: fine-focus sealed tube	θmax = 28.3°, θmin = 1.8°
ω scans	h = −16→16
29662 measured reflections	k = −12→12
6300 independent reflections	l = −29→29
4886 reflections with I > 2σ(I)

Refinement

Refinement on F^2	4 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.057	H-atom parameters constrained
wR(F^2) = 0.155	w = 1/[σ^2(Fo^2) + (0.0756P)^2 + 0.7147P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
6300 reflections	Δρmax = 0.30 e Å^−3
356 parameters	Δρmin = −0.20 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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
F1	1.42983 (13)	−0.1726 (2)	0.03334 (8)	0.1156 (6)
F2	1.15354 (12)	−0.15319 (15)	0.14980 (7)	0.0922 (5)
O1	0.75919 (11)	0.28958 (15)	0.18945 (6)	0.0609 (4)
O2	0.86504 (9)	0.55718 (14)	0.00609 (5)	0.0492 (3)
N1	0.78219 (10)	0.71854 (14)	0.10329 (6)	0.0426 (3)
N2	1.01135 (10)	0.54887 (15)	0.08094 (6)	0.0457 (3)
H2	1.0612	0.5404	0.0589	0.055*
C1	1.21887 (15)	0.0862 (2)	0.03545 (9)	0.0555 (4)
H1	1.1947	0.1707	0.0158	0.067*
C2	1.30872 (17)	0.0194 (3)	0.01994 (10)	0.0692 (6)
H2A	1.3453	0.0587	−0.0092	0.083*
C3	1.34241 (18)	−0.1056 (3)	0.04851 (11)	0.0738 (6)
C4	1.29191 (19)	−0.1656 (3)	0.09195 (12)	0.0755 (6)
H4	1.3160	−0.2509	0.1109	0.091*
C5	1.20386 (16)	−0.0946 (2)	0.10660 (10)	0.0595 (5)
C6	1.16360 (13)	0.03136 (17)	0.07927 (8)	0.0463 (4)
C7	1.06742 (13)	0.10538 (17)	0.09596 (8)	0.0439 (4)
C8	1.05427 (14)	0.1245 (2)	0.15593 (8)	0.0515 (4)
H8	1.1059	0.0888	0.1864	0.062*
C9	0.96640 (14)	0.19527 (19)	0.17080 (8)	0.0495 (4)
H9	0.9587	0.2058	0.2111	0.059*
C10	0.88866 (13)	0.25143 (16)	0.12608 (7)	0.0416 (3)
C11	0.90091 (13)	0.23278 (17)	0.06626 (7)	0.0444 (4)
H11	0.8496	0.2694	0.0359	0.053*
C12	0.98902 (13)	0.16000 (17)	0.05137 (8)	0.0450 (4)
H12	0.9958	0.1475	0.0110	0.054*
C13	0.79685 (13)	0.33090 (17)	0.14605 (7)	0.0422 (3)
C14	0.75582 (11)	0.46789 (16)	0.11342 (7)	0.0370 (3)
H14	0.7254	0.4442	0.0718	0.044*
C15	0.67061 (12)	0.54637 (17)	0.14317 (7)	0.0396 (3)
H15	0.6977	0.5545	0.1864	0.048*
C16	0.67149 (12)	0.69620 (18)	0.11570 (7)	0.0442 (4)
H16	0.6214	0.6992	0.0777	0.053*
C17	0.64921 (16)	0.8225 (2)	0.15536 (10)	0.0655 (5)
H17A	0.6160	0.7899	0.1892	0.079*	0.429 (4)
H17B	0.6022	0.8918	0.1324	0.079*	0.429 (4)
H17C	0.5767	0.8579	0.1433	0.079*	0.571 (4)
H17D	0.6573	0.7934	0.1973	0.079*	0.571 (4)
C18	0.7598 (4)	0.8885 (6)	0.1772 (2)	0.0596 (8)	0.429 (4)
H18A	0.7543	0.9919	0.1808	0.072*	0.429 (4)
H18B	0.7901	0.8494	0.2162	0.072*	0.429 (4)
C18'	0.7266 (3)	0.9325 (4)	0.14717 (19)	0.0596 (8)	0.571 (4)
H18C	0.7450	0.9886	0.1837	0.072*	0.571 (4)
H18D	0.6981	0.9965	0.1145	0.072*	0.571 (4)
C19	0.82659 (15)	0.85131 (19)	0.13188 (10)	0.0574 (5)
H19A	0.9004	0.8368	0.1506	0.069*	0.429 (4)
H19B	0.8247	0.9274	0.1022	0.069*	0.429 (4)
H19C	0.8629	0.9068	0.1045	0.069*	0.571 (4)
H19D	0.8768	0.8308	0.1681	0.069*	0.571 (4)
C20	0.84415 (12)	0.58513 (16)	0.11279 (7)	0.0364 (3)
C21	0.56087 (12)	0.47812 (19)	0.13646 (7)	0.0436 (4)
C22	0.51065 (14)	0.4564 (2)	0.18619 (8)	0.0533 (4)
H22	0.5462	0.4800	0.2244	0.064*
C23	0.40755 (16)	0.3997 (2)	0.17992 (11)	0.0683 (6)
H23	0.3746	0.3860	0.2138	0.082*
C24	0.35447 (16)	0.3642 (3)	0.12446 (11)	0.0729 (6)
H24	0.2856	0.3259	0.1204	0.088*
C25	0.40302 (17)	0.3850 (3)	0.07466 (11)	0.0801 (7)
H25	0.3667	0.3616	0.0366	0.096*
C26	0.50557 (16)	0.4405 (3)	0.08058 (9)	0.0691 (6)
H26	0.5381	0.4528	0.0464	0.083*
C27	0.90604 (12)	0.56227 (16)	0.05899 (7)	0.0388 (3)
C28	1.02933 (13)	0.55045 (17)	0.14422 (8)	0.0441 (4)
C29	1.12487 (15)	0.5294 (2)	0.18212 (10)	0.0608 (5)
H29	1.1885	0.5134	0.1670	0.073*
C30	1.12263 (17)	0.5329 (3)	0.24354 (10)	0.0714 (6)
H30	1.1858	0.5176	0.2701	0.086*
C31	1.02894 (18)	0.5586 (2)	0.26619 (9)	0.0666 (6)
H31	1.0297	0.5612	0.3077	0.080*
C32	0.93354 (15)	0.5804 (2)	0.22761 (8)	0.0520 (4)
H32	0.8702	0.5983	0.2429	0.062*
C33	0.93381 (12)	0.57534 (16)	0.16614 (7)	0.0399 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0836 (10)	0.1401 (15)	0.1255 (13)	0.0590 (10)	0.0234 (9)	−0.0066 (11)
F2	0.1023 (10)	0.0606 (8)	0.1199 (12)	0.0165 (7)	0.0365 (9)	0.0358 (7)
O1	0.0647 (8)	0.0607 (8)	0.0624 (8)	0.0027 (6)	0.0259 (6)	0.0170 (6)
O2	0.0497 (7)	0.0612 (7)	0.0390 (6)	0.0094 (5)	0.0141 (5)	0.0031 (5)
N1	0.0406 (7)	0.0391 (7)	0.0500 (7)	0.0036 (5)	0.0127 (6)	−0.0004 (6)
N2	0.0352 (7)	0.0518 (8)	0.0534 (8)	0.0014 (6)	0.0169 (6)	0.0000 (6)
C1	0.0533 (10)	0.0548 (10)	0.0576 (11)	0.0060 (8)	0.0059 (8)	0.0008 (8)
C2	0.0567 (12)	0.0838 (15)	0.0681 (13)	0.0105 (11)	0.0127 (10)	−0.0012 (11)
C3	0.0564 (12)	0.0861 (16)	0.0771 (15)	0.0250 (11)	0.0040 (11)	−0.0130 (12)
C4	0.0725 (14)	0.0603 (13)	0.0888 (16)	0.0262 (11)	−0.0034 (12)	0.0028 (11)
C5	0.0590 (11)	0.0476 (10)	0.0704 (12)	0.0051 (9)	0.0048 (9)	0.0062 (9)
C6	0.0427 (8)	0.0398 (8)	0.0538 (9)	0.0012 (7)	−0.0011 (7)	−0.0036 (7)
C7	0.0421 (8)	0.0341 (8)	0.0542 (9)	−0.0016 (6)	0.0035 (7)	−0.0007 (7)
C8	0.0502 (9)	0.0526 (10)	0.0488 (9)	0.0065 (8)	−0.0017 (7)	0.0067 (8)
C9	0.0538 (10)	0.0495 (9)	0.0444 (9)	0.0028 (8)	0.0054 (7)	0.0051 (7)
C10	0.0428 (8)	0.0335 (7)	0.0479 (9)	−0.0024 (6)	0.0055 (7)	0.0022 (6)
C11	0.0464 (9)	0.0381 (8)	0.0457 (9)	0.0027 (7)	−0.0022 (7)	−0.0012 (7)
C12	0.0501 (9)	0.0391 (8)	0.0445 (9)	0.0023 (7)	0.0027 (7)	−0.0037 (7)
C13	0.0411 (8)	0.0418 (8)	0.0437 (8)	−0.0059 (6)	0.0065 (6)	0.0008 (7)
C14	0.0335 (7)	0.0415 (8)	0.0369 (7)	−0.0009 (6)	0.0083 (6)	−0.0002 (6)
C15	0.0329 (7)	0.0515 (9)	0.0352 (7)	0.0002 (6)	0.0075 (6)	−0.0035 (6)
C16	0.0377 (8)	0.0491 (9)	0.0464 (9)	0.0063 (7)	0.0086 (6)	−0.0045 (7)
C17	0.0613 (12)	0.0610 (12)	0.0785 (14)	0.0111 (9)	0.0248 (10)	−0.0178 (10)
C18	0.081 (2)	0.0434 (17)	0.059 (2)	0.0007 (14)	0.0238 (18)	−0.0071 (13)
C18'	0.081 (2)	0.0434 (17)	0.059 (2)	0.0007 (14)	0.0238 (18)	−0.0071 (13)
C19	0.0568 (10)	0.0402 (9)	0.0761 (13)	−0.0026 (8)	0.0127 (9)	−0.0041 (8)
C20	0.0360 (7)	0.0383 (8)	0.0361 (7)	0.0008 (6)	0.0100 (6)	0.0007 (6)
C21	0.0337 (7)	0.0528 (9)	0.0453 (8)	0.0018 (7)	0.0096 (6)	−0.0011 (7)
C22	0.0433 (9)	0.0679 (12)	0.0514 (10)	−0.0011 (8)	0.0159 (7)	−0.0054 (8)
C23	0.0537 (11)	0.0800 (14)	0.0789 (14)	−0.0079 (10)	0.0350 (10)	−0.0065 (11)
C24	0.0433 (10)	0.0815 (15)	0.0966 (17)	−0.0167 (10)	0.0188 (11)	−0.0200 (13)
C25	0.0536 (12)	0.114 (2)	0.0702 (14)	−0.0231 (13)	0.0027 (10)	−0.0201 (13)
C26	0.0494 (10)	0.1077 (18)	0.0503 (11)	−0.0186 (11)	0.0077 (8)	−0.0067 (11)
C27	0.0398 (8)	0.0361 (7)	0.0433 (8)	0.0023 (6)	0.0151 (6)	0.0034 (6)
C28	0.0390 (8)	0.0403 (8)	0.0528 (9)	−0.0031 (6)	0.0062 (7)	0.0032 (7)
C29	0.0388 (9)	0.0633 (12)	0.0782 (13)	0.0002 (8)	0.0025 (9)	0.0065 (10)
C30	0.0536 (11)	0.0810 (15)	0.0715 (14)	−0.0087 (10)	−0.0167 (10)	0.0174 (11)
C31	0.0689 (13)	0.0795 (14)	0.0469 (10)	−0.0198 (11)	−0.0051 (9)	0.0107 (9)
C32	0.0521 (10)	0.0615 (11)	0.0420 (9)	−0.0122 (8)	0.0061 (7)	0.0022 (8)
C33	0.0369 (7)	0.0389 (8)	0.0441 (8)	−0.0050 (6)	0.0069 (6)	0.0019 (6)

Geometric parameters (Å, º)

F1—C3	1.354 (2)	C17—C18'	1.446 (4)
F2—C5	1.352 (2)	C17—C18	1.534 (5)
O1—C13	1.2096 (19)	C17—H17A	0.9700
O2—C27	1.2211 (19)	C17—H17B	0.9700
N1—C19	1.464 (2)	C17—H17C	0.9700
N1—C20	1.4655 (19)	C17—H17D	0.9700
N1—C16	1.478 (2)	C18—C19	1.457 (5)
N2—C27	1.349 (2)	C18—H18A	0.9700
N2—C28	1.403 (2)	C18—H18B	0.9700
N2—H2	0.8600	C18'—C19	1.552 (4)
C1—C2	1.382 (3)	C18'—H18C	0.9700
C1—C6	1.387 (3)	C18'—H18D	0.9700
C1—H1	0.9300	C19—H19A	0.9700
C2—C3	1.365 (3)	C19—H19B	0.9700
C2—H2A	0.9300	C19—H19C	0.9700
C3—C4	1.362 (3)	C19—H19D	0.9700
C4—C5	1.374 (3)	C20—C33	1.518 (2)
C4—H4	0.9300	C20—C27	1.549 (2)
C5—C6	1.383 (2)	C21—C22	1.380 (2)
C6—C7	1.491 (2)	C21—C26	1.383 (3)
C7—C12	1.391 (2)	C22—C23	1.390 (3)
C7—C8	1.392 (2)	C22—H22	0.9300
C8—C9	1.373 (2)	C23—C24	1.361 (3)
C8—H8	0.9300	C23—H23	0.9300
C9—C10	1.393 (2)	C24—C25	1.367 (3)
C9—H9	0.9300	C24—H24	0.9300
C10—C11	1.385 (2)	C25—C26	1.379 (3)
C10—C13	1.499 (2)	C25—H25	0.9300
C11—C12	1.385 (2)	C26—H26	0.9300
C11—H11	0.9300	C28—C29	1.378 (2)
C12—H12	0.9300	C28—C33	1.388 (2)
C13—C14	1.522 (2)	C29—C30	1.383 (3)
C14—C15	1.534 (2)	C29—H29	0.9300
C14—C20	1.561 (2)	C30—C31	1.376 (3)
C14—H14	0.9800	C30—H30	0.9300
C15—C21	1.508 (2)	C31—C32	1.385 (3)
C15—C16	1.526 (2)	C31—H31	0.9300
C15—H15	0.9800	C32—C33	1.381 (2)
C16—C17	1.527 (2)	C32—H32	0.9300
C16—H16	0.9800
C19—N1—C20	119.52 (13)	C18'—C17—H17D	110.4
C19—N1—C16	110.16 (13)	C16—C17—H17D	110.4
C20—N1—C16	110.51 (12)	H17C—C17—H17D	108.6
C27—N2—C28	111.48 (13)	C19—C18—C17	106.0 (3)
C27—N2—H2	124.3	C19—C18—H18A	110.5
C28—N2—H2	124.3	C17—C18—H18A	110.5
C2—C1—C6	122.21 (19)	C19—C18—H18B	110.5
C2—C1—H1	118.9	C17—C18—H18B	110.5
C6—C1—H1	118.9	H18A—C18—H18B	108.7
C3—C2—C1	118.2 (2)	C17—C18'—C19	105.6 (2)
C3—C2—H2A	120.9	C17—C18'—H18C	110.6
C1—C2—H2A	120.9	C19—C18'—H18C	110.6
F1—C3—C4	118.6 (2)	C17—C18'—H18D	110.6
F1—C3—C2	118.8 (2)	C19—C18'—H18D	110.6
C4—C3—C2	122.7 (2)	H18C—C18'—H18D	108.8
C3—C4—C5	117.2 (2)	C18—C19—N1	106.5 (2)
C3—C4—H4	121.4	N1—C19—C18'	103.87 (18)
C5—C4—H4	121.4	C18—C19—H19A	110.4
F2—C5—C4	117.51 (18)	N1—C19—H19A	110.4
F2—C5—C6	118.67 (18)	C18—C19—H19B	110.4
C4—C5—C6	123.8 (2)	N1—C19—H19B	110.4
C5—C6—C1	115.88 (17)	H19A—C19—H19B	108.6
C5—C6—C7	122.52 (17)	N1—C19—H19C	111.0
C1—C6—C7	121.59 (15)	C18'—C19—H19C	111.0
C12—C7—C8	118.18 (16)	N1—C19—H19D	111.0
C12—C7—C6	120.24 (16)	C18'—C19—H19D	111.0
C8—C7—C6	121.57 (15)	H19C—C19—H19D	109.0
C9—C8—C7	121.07 (16)	N1—C20—C33	118.78 (13)
C9—C8—H8	119.5	N1—C20—C27	108.89 (12)
C7—C8—H8	119.5	C33—C20—C27	101.75 (12)
C8—C9—C10	120.65 (16)	N1—C20—C14	103.27 (11)
C8—C9—H9	119.7	C33—C20—C14	113.37 (12)
C10—C9—H9	119.7	C27—C20—C14	110.84 (12)
C11—C10—C9	118.73 (15)	C22—C21—C26	117.80 (16)
C11—C10—C13	123.87 (14)	C22—C21—C15	120.53 (15)
C9—C10—C13	117.40 (15)	C26—C21—C15	121.62 (15)
C12—C11—C10	120.51 (15)	C21—C22—C23	120.75 (18)
C12—C11—H11	119.7	C21—C22—H22	119.6
C10—C11—H11	119.7	C23—C22—H22	119.6
C11—C12—C7	120.86 (16)	C24—C23—C22	120.42 (19)
C11—C12—H12	119.6	C24—C23—H23	119.8
C7—C12—H12	119.6	C22—C23—H23	119.8
O1—C13—C10	119.98 (15)	C23—C24—C25	119.61 (19)
O1—C13—C14	120.52 (15)	C23—C24—H24	120.2
C10—C13—C14	119.42 (13)	C25—C24—H24	120.2
C13—C14—C15	113.52 (13)	C24—C25—C26	120.3 (2)
C13—C14—C20	113.61 (12)	C24—C25—H25	119.9
C15—C14—C20	102.61 (12)	C26—C25—H25	119.9
C13—C14—H14	108.9	C25—C26—C21	121.12 (19)
C15—C14—H14	108.9	C25—C26—H26	119.4
C20—C14—H14	108.9	C21—C26—H26	119.4
C21—C15—C16	114.09 (13)	O2—C27—N2	126.71 (14)
C21—C15—C14	116.62 (13)	O2—C27—C20	125.07 (14)
C16—C15—C14	102.18 (12)	N2—C27—C20	108.22 (13)
C21—C15—H15	107.8	C29—C28—C33	121.90 (17)
C16—C15—H15	107.8	C29—C28—N2	127.86 (16)
C14—C15—H15	107.8	C33—C28—N2	110.23 (14)
N1—C16—C15	105.67 (12)	C28—C29—C30	117.55 (19)
N1—C16—C17	105.33 (14)	C28—C29—H29	121.2
C15—C16—C17	117.11 (15)	C30—C29—H29	121.2
N1—C16—H16	109.5	C31—C30—C29	121.45 (18)
C15—C16—H16	109.5	C31—C30—H30	119.3
C17—C16—H16	109.5	C29—C30—H30	119.3
C18'—C17—C16	106.51 (19)	C30—C31—C32	120.43 (19)
C16—C17—C18	104.8 (2)	C30—C31—H31	119.8
C16—C17—H17A	110.8	C32—C31—H31	119.8
C18—C17—H17A	110.8	C33—C32—C31	119.01 (18)
C16—C17—H17B	110.8	C33—C32—H32	120.5
C18—C17—H17B	110.8	C31—C32—H32	120.5
H17A—C17—H17B	108.9	C32—C33—C28	119.65 (15)
C18'—C17—H17C	110.4	C32—C33—C20	132.10 (15)
C16—C17—H17C	110.4	C28—C33—C20	108.17 (13)
C6—C1—C2—C3	0.9 (3)	C16—N1—C19—C18	17.6 (3)
C1—C2—C3—F1	179.5 (2)	C20—N1—C19—C18'	−145.4 (2)
C1—C2—C3—C4	−0.9 (4)	C16—N1—C19—C18'	−15.8 (2)
F1—C3—C4—C5	179.6 (2)	C17—C18'—C19—N1	27.8 (3)
C2—C3—C4—C5	−0.1 (4)	C19—N1—C20—C33	19.1 (2)
C3—C4—C5—F2	−179.8 (2)	C16—N1—C20—C33	−110.25 (15)
C3—C4—C5—C6	1.0 (3)	C19—N1—C20—C27	−96.55 (17)
F2—C5—C6—C1	179.88 (18)	C16—N1—C20—C27	134.06 (13)
C4—C5—C6—C1	−1.0 (3)	C19—N1—C20—C14	145.62 (14)
F2—C5—C6—C7	0.5 (3)	C16—N1—C20—C14	16.22 (15)
C4—C5—C6—C7	179.63 (19)	C13—C14—C20—N1	−157.37 (12)
C2—C1—C6—C5	0.0 (3)	C15—C14—C20—N1	−34.41 (14)
C2—C1—C6—C7	179.36 (18)	C13—C14—C20—C33	−27.52 (17)
C5—C6—C7—C12	−136.73 (18)	C15—C14—C20—C33	95.44 (14)
C1—C6—C7—C12	43.9 (2)	C13—C14—C20—C27	86.17 (15)
C5—C6—C7—C8	44.6 (2)	C15—C14—C20—C27	−150.87 (12)
C1—C6—C7—C8	−134.78 (19)	C16—C15—C21—C22	−111.32 (18)
C12—C7—C8—C9	0.0 (3)	C14—C15—C21—C22	129.83 (17)
C6—C7—C8—C9	178.73 (16)	C16—C15—C21—C26	66.1 (2)
C7—C8—C9—C10	−0.8 (3)	C14—C15—C21—C26	−52.7 (2)
C8—C9—C10—C11	0.9 (3)	C26—C21—C22—C23	−0.5 (3)
C8—C9—C10—C13	−178.25 (16)	C15—C21—C22—C23	177.01 (18)
C9—C10—C11—C12	−0.2 (2)	C21—C22—C23—C24	0.2 (3)
C13—C10—C11—C12	178.90 (15)	C22—C23—C24—C25	−0.2 (4)
C10—C11—C12—C7	−0.6 (2)	C23—C24—C25—C26	0.6 (4)
C8—C7—C12—C11	0.7 (2)	C24—C25—C26—C21	−1.0 (4)
C6—C7—C12—C11	−178.04 (15)	C22—C21—C26—C25	0.9 (3)
C11—C10—C13—O1	143.39 (17)	C15—C21—C26—C25	−176.6 (2)
C9—C10—C13—O1	−37.5 (2)	C28—N2—C27—O2	−175.97 (15)
C11—C10—C13—C14	−39.9 (2)	C28—N2—C27—C20	3.84 (17)
C9—C10—C13—C14	139.20 (15)	N1—C20—C27—O2	−56.15 (19)
O1—C13—C14—C15	3.2 (2)	C33—C20—C27—O2	177.63 (15)
C10—C13—C14—C15	−173.45 (13)	C14—C20—C27—O2	56.79 (19)
O1—C13—C14—C20	119.99 (17)	N1—C20—C27—N2	124.03 (13)
C10—C13—C14—C20	−56.69 (18)	C33—C20—C27—N2	−2.19 (16)
C13—C14—C15—C21	−72.60 (17)	C14—C20—C27—N2	−123.03 (13)
C20—C14—C15—C21	164.38 (13)	C27—N2—C28—C29	175.07 (17)
C13—C14—C15—C16	162.29 (12)	C27—N2—C28—C33	−4.09 (19)
C20—C14—C15—C16	39.26 (14)	C33—C28—C29—C30	0.4 (3)
C19—N1—C16—C15	−125.74 (14)	N2—C28—C29—C30	−178.66 (18)
C20—N1—C16—C15	8.51 (16)	C28—C29—C30—C31	−0.9 (3)
C19—N1—C16—C17	−1.15 (19)	C29—C30—C31—C32	0.6 (3)
C20—N1—C16—C17	133.09 (15)	C30—C31—C32—C33	0.3 (3)
C21—C15—C16—N1	−156.70 (13)	C31—C32—C33—C28	−0.9 (3)
C14—C15—C16—N1	−29.93 (15)	C31—C32—C33—C20	175.64 (17)
C21—C15—C16—C17	86.42 (18)	C29—C28—C33—C32	0.5 (3)
C14—C15—C16—C17	−146.81 (15)	N2—C28—C33—C32	179.70 (15)
N1—C16—C17—C18'	19.2 (3)	C29—C28—C33—C20	−176.78 (16)
C15—C16—C17—C18'	136.3 (2)	N2—C28—C33—C20	2.44 (18)
N1—C16—C17—C18	−14.8 (3)	N1—C20—C33—C32	63.6 (2)
C15—C16—C17—C18	102.3 (3)	C27—C20—C33—C32	−176.98 (17)
C16—C17—C18—C19	25.7 (4)	C14—C20—C33—C32	−57.9 (2)
C16—C17—C18'—C19	−28.9 (3)	N1—C20—C33—C28	−119.62 (15)
C17—C18—C19—N1	−26.6 (4)	C27—C20—C33—C28	−0.18 (16)
C20—N1—C19—C18	−111.9 (3)	C14—C20—C33—C28	118.87 (14)

Hydrogen-bond geometry (Å, º)

Cg is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2^i	0.86	2.06	2.854 (2)	154
C18—H18B···O1^ii	0.97	2.36	3.175 (6)	141
C19—H19C···Cg^iii	0.97	2.91	3.659 (2)	135

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+3/2, y+1/2, −z+1/2; (iii) x, y+1, z.