Crystal structures of 2,3,7,8,12,13,17,18-octa­bromo-5,10,15,20-tetra­kis­(penta­fluoro­phen­yl)porphyrin as the chloro­form monosolvate and tetra­hydro­furan monosolvate

Kingsbury, C.J.; Flanagan, K.J.; Kielmann, M.; Twamley, B.; Senge, M.O.

doi:10.1107/S2056989020000432

Crystal structures of 2,3,7,8,12,13,17,18-octabromo-5,10,15,20-tetrakis(pentafluorophenyl)porphyrin as the chloroform monosolvate and tetrahydrofuran monosolvate

C. J. Kingsbury, K. J. Flanagan, M. Kielmann, B. Twamley and M. O. Senge

The crystal structures of the title compounds, two solvates (CHCl₃ and THF) of a symmetric and highly substituted porphyrin, OBrTPFPP, are described. These structures each feature a non-planar porphyrin ring, exhibiting a similar conformation of the strained ring independent of solvent identity. These distorted porphyrins are able to form hydrogen bonds and sub-van der Waals halogen interactions with enclathrated solvent; supramolecular interactions of proximal macrocycles are additionally affected by solvent choice.

Keywords: crystal structure; symmetrical porphyrins; non-planar porphyrins; halogenated porphyrins; solvent interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989020000432/tx2016sup1.cif Contains datablocks 1_CHCl3, 1_THF
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989020000432/tx20161_CHCl3sup4.hkl Contains datablock 1_CHCl3
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989020000432/tx20161_THFsup5.hkl Contains datablock 1_THF

CCDC references: 1977525; 1977524

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.004 Å
Mean (C-C) = 0.008 Å
Disorder in main residue
R factor = 0.020
wR factor = 0.043
Data-to-parameter ratio = 24.0

checkCIF/PLATON results

No syntax errors found



Datablock: 1_CHCl3



Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.3 Note
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          1 Check

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          4 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         17 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records         12 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          3 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          4 Report
PLAT186_ALERT_4_G The CIF-Embedded .res File Contains ISOR Records          1 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        14% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  2  )       100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  3  )       100% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  2  )       4.41 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  3  )       0.59 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  Cl3S     ..C6               3.23 Ang.
                                                      x,y,z  =      1_555 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  Cl4S     ..C6               3.14 Ang.
                                                      x,y,z  =      1_555 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  Cl5S     ..C19              3.17 Ang.
                                                      x,y,z  =      1_555 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  F19      ..C54              2.82 Ang.
                                              2-x,1/2+y,2-z  =      2_757 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  F19      ..C54B             2.96 Ang.
                                              2-x,1/2+y,2-z  =      2_757 Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact Br4      ..F7               3.18 Ang.
                                                    x,1+y,z  =      1_565 Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact Br4      ..F7               3.21 Ang.
                                              2-x,1/2+y,1-z  =      2_756 Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact Br6      ..F9               3.11 Ang.
                                             1-x,-1/2+y,1-z  =      2_646 Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact Br8      ..F3B              3.11 Ang.
                                                   -1+x,y,z  =      1_455 Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact Br8      ..F3               3.15 Ang.
                                                   -1+x,y,z  =      1_455 Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact F14      ..F4               2.77 Ang.
                                                   -1+x,y,z  =      1_455 Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact F19      ..F3               2.80 Ang.
                                              2-x,1/2+y,2-z  =      2_757 Check
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          1 Note
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............        244 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          7 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         13 Info

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  16 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
  10 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check




Datablock: 1_THF



Alert level B
PLAT434_ALERT_2_B Short Inter HL..HL Contact Br5      ..Br5              3.23 Ang.
                                                 1-x,-y,1-z  =      3_656 Check

Alert level C
PLAT243_ALERT_4_C High   Solvent Ueq as Compared to Neighbors of        C29 Check
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0077 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      7.634 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.026 Check
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  0.89A   From Br5             2.12 eA-3
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         10 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         44 Report
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large      36.97 Why ?
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          2 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          2 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          2 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        29% Note
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O25            107.9 Degree
PLAT432_ALERT_2_G Short Inter X...Y Contact  Br7      ..C23A             3.34 Ang.
                                                   x,-1+y,z  =      1_545 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  F8       ..C1               2.93 Ang.
                                          3/2-x,1/2+y,1/2-z  =      2_655 Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact Br2      ..F6               3.12 Ang.
                                          3/2-x,1/2+y,1/2-z  =      2_655 Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact Br2      ..F11A             3.21 Ang.
                                                    x,1+y,z  =      1_565 Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact Br3      ..F3A              3.12 Ang.
                                          1/2+x,3/2-y,1/2+z  =      4_676 Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact Br3      ..F3B              3.19 Ang.
                                          1/2+x,3/2-y,1/2+z  =      4_676 Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact Br6      ..F13B             3.09 Ang.
                                                 1-x,-y,1-z  =      3_656 Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact Br7      ..F2A              3.05 Ang.
                                                   x,-1+y,z  =      1_545 Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact Br7      ..F2B              3.08 Ang.
                                                   x,-1+y,z  =      1_545 Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact Br7      ..F14B             3.20 Ang.
                                        -1/2+x,1/2-y,-1/2+z  =      4_565 Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact Br8      ..F9               3.20 Ang.
                                        -1/2+x,3/2-y,-1/2+z  =      4_575 Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact F8       ..F5B              2.75 Ang.
                                          3/2-x,1/2+y,1/2-z  =      2_655 Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact F10      ..F12B             2.74 Ang.
                                                    x,1+y,z  =      1_565 Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact F10      ..F12A             2.78 Ang.
                                                    x,1+y,z  =      1_565 Check
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............        718 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         16 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  22 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 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 top

For both structures, data collection: APEX3 (Bruker, 2017); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: Shelxle (Hübschle et al., 2011); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

2,3,7,8,12,13,17,18-Octabromo-5,10,15,20-tetrakis(pentafluorophenyl)porphyrin chloroform monosolvate (1_CHCl3) top

Crystal data top

C₄₄H₂Br₈F₂₀N₄·CHCl₃	F(000) = 1624
M_r = 1725.14	D_x = 2.276 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 15.5162 (7) Å	Cell parameters from 9974 reflections
b = 6.8288 (3) Å	θ = 2.6–32.5°
c = 24.5631 (12) Å	µ = 6.65 mm⁻¹
β = 104.683 (1)°	T = 100 K
V = 2517.6 (2) Å³	Block, blue
Z = 2	0.31 × 0.30 × 0.11 mm

Data collection top

Bruker APEXII CCD diffractometer	18291 independent reflections
Radiation source: microfocus sealed X-ray tube, graphite-monochromated	17164 reflections with I > 2σ(I)
Mirror optics monochromator	R_int = 0.028
Detector resolution: 7.9 pixels mm^-1	θ_max = 32.6°, θ_min = 1.4°
φ and ω scans	h = −23→23
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −10→10
T_min = 0.458, T_max = 0.746	l = −37→36
107677 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.020	w = 1/[σ²(F_o²) + (0.0025P)² + 1.005P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.043	(Δ/σ)_max = 0.002
S = 1.03	Δρ_max = 0.52 e Å⁻³
18291 reflections	Δρ_min = −0.46 e Å⁻³
763 parameters	Absolute structure: Refined as an inversion twin.
244 restraints	Absolute structure parameter: 0.010 (4)
Primary atom site location: dual

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.79032 (16)	0.5406 (4)	0.87273 (10)	0.0134 (4)
Br1	0.87104 (2)	0.43518 (5)	0.99180 (2)	0.02349 (6)
C2	0.86821 (16)	0.5046 (4)	0.91809 (10)	0.0152 (4)
Br2	1.05536 (2)	0.43897 (5)	0.93835 (2)	0.02288 (6)
C3	0.94138 (16)	0.5053 (4)	0.89661 (10)	0.0153 (4)
Br3	1.06413 (2)	0.81653 (4)	0.70329 (2)	0.02160 (6)
C4	0.91257 (15)	0.5427 (4)	0.83707 (10)	0.0132 (4)
Br4	0.92250 (2)	0.68017 (4)	0.57534 (2)	0.01783 (5)
C5	0.96138 (16)	0.5753 (4)	0.79756 (10)	0.0145 (4)
Br5	0.67971 (2)	−0.08433 (4)	0.56768 (2)	0.02307 (5)
C6	0.92364 (15)	0.5776 (4)	0.73877 (10)	0.0134 (4)
F6	0.94084 (10)	0.1746 (3)	0.61796 (6)	0.0201 (3)
Br6	0.49352 (2)	−0.08753 (4)	0.62177 (2)	0.02119 (5)
C7	0.96548 (16)	0.6523 (4)	0.69563 (10)	0.0154 (4)
F7	0.98329 (10)	0.0661 (3)	0.52270 (7)	0.0227 (3)
Br7	0.37497 (2)	0.69017 (4)	0.73639 (2)	0.01604 (5)
C8	0.91110 (16)	0.5994 (4)	0.64558 (10)	0.0139 (4)
F8	0.86376 (11)	0.1210 (3)	0.42128 (7)	0.0246 (4)
Br8	0.51364 (2)	0.86107 (4)	0.86350 (2)	0.01969 (5)
C9	0.83861 (15)	0.4866 (3)	0.65798 (10)	0.0133 (4)
F9	0.70704 (11)	0.3005 (3)	0.41561 (6)	0.0247 (3)
C10	0.77912 (15)	0.3636 (4)	0.62036 (10)	0.0139 (4)
F10	0.66599 (10)	0.4240 (3)	0.51083 (6)	0.0229 (3)
C11	0.70159 (15)	0.2861 (4)	0.63184 (10)	0.0137 (4)
F11	0.41703 (10)	0.4175 (3)	0.58292 (6)	0.0224 (3)
C12	0.64841 (16)	0.1194 (4)	0.60940 (10)	0.0150 (4)
F12	0.24742 (11)	0.2960 (3)	0.54385 (7)	0.0268 (4)
C13	0.57470 (16)	0.1181 (4)	0.63059 (10)	0.0149 (4)
F13	0.16081 (11)	0.1268 (3)	0.61447 (9)	0.0321 (4)
C14	0.57932 (15)	0.2834 (4)	0.66693 (10)	0.0130 (4)
F14	0.24506 (11)	0.0721 (3)	0.72457 (8)	0.0270 (4)
C15	0.51835 (15)	0.3577 (3)	0.69576 (10)	0.0127 (4)
F15	0.41634 (10)	0.1838 (2)	0.76383 (6)	0.0196 (3)
C16	0.54601 (15)	0.4764 (3)	0.74374 (10)	0.0126 (4)
F16	0.59460 (13)	0.3120 (3)	0.91627 (7)	0.0328 (4)
C17	0.49068 (15)	0.6028 (3)	0.76885 (10)	0.0138 (4)
F17	0.54619 (14)	0.3700 (4)	1.01268 (8)	0.0471 (6)
C18	0.54346 (15)	0.6649 (4)	0.81857 (10)	0.0141 (4)
F18	0.60364 (13)	0.6916 (4)	1.07618 (7)	0.0433 (5)
C19	0.63021 (15)	0.5740 (4)	0.82428 (10)	0.0133 (4)
F19	0.71156 (14)	0.9551 (4)	1.04248 (8)	0.0435 (5)
C20	0.70187 (16)	0.5724 (4)	0.87352 (10)	0.0140 (4)
F20	0.76215 (12)	0.8962 (3)	0.94747 (8)	0.0315 (4)
N21	0.82117 (13)	0.5520 (3)	0.82522 (8)	0.0122 (3)
H21	0.786401	0.563972	0.790997	0.015*
N22	0.84463 (13)	0.4908 (3)	0.71443 (8)	0.0129 (4)
N23	0.65875 (13)	0.3736 (3)	0.66794 (8)	0.0136 (4)
H23	0.679701	0.475296	0.689186	0.016*
Cl1S	0.8289 (3)	1.0578 (6)	0.84825 (15)	0.0405 (6)	0.882 (7)
F5	1.0834 (12)	0.304 (4)	0.7761 (9)	0.0289 (15)	0.462 (7)
F4	1.2643 (6)	0.3383 (11)	0.8118 (4)	0.0363 (11)	0.462 (7)
F3	1.3335 (5)	0.6633 (11)	0.8705 (3)	0.0379 (10)	0.462 (7)
F2	1.2238 (5)	0.9445 (11)	0.8947 (3)	0.0382 (11)	0.462 (7)
F1	1.0460 (9)	0.900 (3)	0.8631 (7)	0.0303 (14)	0.462 (7)
C1S	0.7822 (3)	1.0817 (7)	0.7756 (2)	0.0287 (9)	0.882 (7)
H	0.762829	1.220837	0.767873	0.034*	0.882 (7)
Cl2S	0.68818 (11)	0.9313 (2)	0.75235 (8)	0.0489 (5)	0.882 (7)
Cl3S	0.86152 (16)	1.0294 (2)	0.73764 (8)	0.0461 (4)	0.882 (7)
N24	0.63172 (13)	0.4721 (3)	0.77706 (8)	0.0132 (4)
C51	1.0608 (6)	0.603 (3)	0.8183 (10)	0.0210 (7)	0.462 (7)
C52	1.0984 (7)	0.767 (2)	0.8488 (8)	0.0255 (12)	0.462 (7)
C53	1.1905 (7)	0.7875 (14)	0.8658 (6)	0.0287 (14)	0.462 (7)
C54	1.2450 (6)	0.6439 (12)	0.8522 (5)	0.0292 (14)	0.462 (7)
C55	1.2074 (9)	0.4800 (15)	0.8217 (6)	0.0280 (13)	0.462 (7)
C56	1.1154 (9)	0.460 (2)	0.8047 (8)	0.0241 (9)	0.462 (7)
C2S	0.770 (2)	1.107 (6)	0.7747 (14)	0.0287 (9)	0.118 (7)
HA	0.763429	1.250725	0.766630	0.034*	0.118 (7)
C51B	1.0594 (5)	0.616 (2)	0.8184 (8)	0.0210 (7)	0.538 (7)
C52B	1.0853 (6)	0.793 (2)	0.8456 (7)	0.0255 (12)	0.538 (7)
C53B	1.1752 (6)	0.8393 (12)	0.8646 (5)	0.0287 (14)	0.538 (7)
C54B	1.2393 (5)	0.7081 (11)	0.8564 (4)	0.0292 (14)	0.538 (7)
C55B	1.2134 (7)	0.5311 (12)	0.8292 (5)	0.0280 (13)	0.538 (7)
C56B	1.1235 (8)	0.4852 (18)	0.8102 (7)	0.0241 (9)	0.538 (7)
F1B	1.0276 (8)	0.927 (2)	0.8547 (6)	0.0303 (14)	0.538 (7)
F2B	1.2028 (4)	1.0127 (9)	0.8910 (3)	0.0382 (11)	0.538 (7)
F3B	1.3255 (4)	0.7480 (10)	0.8757 (3)	0.0379 (10)	0.538 (7)
F4B	1.2721 (5)	0.4032 (10)	0.8213 (3)	0.0363 (11)	0.538 (7)
F5B	1.0987 (10)	0.315 (4)	0.7843 (8)	0.0289 (15)	0.538 (7)
C101	0.80163 (15)	0.3017 (4)	0.56770 (10)	0.0137 (4)
C102	0.88211 (16)	0.2099 (4)	0.56870 (10)	0.0148 (4)
C103	0.90484 (16)	0.1527 (4)	0.52009 (11)	0.0158 (4)
C104	0.84515 (17)	0.1824 (4)	0.46866 (10)	0.0180 (4)
C105	0.76466 (16)	0.2730 (4)	0.46601 (10)	0.0171 (5)
C106	0.74383 (15)	0.3321 (4)	0.51480 (10)	0.0159 (4)
C151	0.42329 (15)	0.3018 (4)	0.67476 (10)	0.0127 (4)
C152	0.37698 (16)	0.3310 (4)	0.61870 (10)	0.0156 (4)
C153	0.28927 (17)	0.2728 (4)	0.59851 (11)	0.0188 (5)
C154	0.24496 (15)	0.1857 (4)	0.63424 (12)	0.0206 (5)
C155	0.28786 (16)	0.1582 (4)	0.69014 (12)	0.0189 (5)
C156	0.37625 (16)	0.2150 (4)	0.70987 (10)	0.0149 (4)
C201	0.67914 (16)	0.6031 (4)	0.92807 (10)	0.0167 (5)
C202	0.62418 (17)	0.4721 (4)	0.94653 (11)	0.0214 (5)
C203	0.59867 (19)	0.5003 (5)	0.99606 (12)	0.0291 (7)
C204	0.62785 (19)	0.6622 (6)	1.02837 (11)	0.0306 (7)
C205	0.68316 (19)	0.7956 (5)	1.01145 (12)	0.0276 (6)
C206	0.70860 (18)	0.7645 (4)	0.96233 (11)	0.0212 (5)
Cl4S	0.8187 (18)	0.975 (3)	0.7296 (6)	0.069 (4)	0.118 (7)
Cl5S	0.6705 (9)	0.989 (2)	0.7786 (10)	0.068 (5)	0.118 (7)
Cl6S	0.839 (2)	1.047 (5)	0.8409 (12)	0.049 (6)	0.118 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0128 (10)	0.0167 (10)	0.0107 (10)	−0.0011 (8)	0.0027 (8)	0.0002 (8)
Br1	0.02061 (12)	0.03766 (15)	0.01195 (10)	0.00155 (11)	0.00370 (9)	0.00789 (11)
C2	0.0145 (11)	0.0201 (11)	0.0109 (10)	−0.0009 (8)	0.0028 (8)	0.0020 (8)
Br2	0.01293 (10)	0.03700 (15)	0.01655 (11)	0.00356 (11)	−0.00026 (8)	0.00561 (11)
C3	0.0113 (10)	0.0210 (11)	0.0123 (10)	−0.0005 (8)	0.0005 (8)	0.0023 (8)
Br3	0.01564 (11)	0.03080 (14)	0.01819 (12)	−0.01240 (10)	0.00399 (9)	0.00174 (10)
C4	0.0095 (9)	0.0170 (10)	0.0118 (10)	−0.0019 (8)	0.0001 (8)	0.0004 (8)
Br4	0.01723 (11)	0.02391 (11)	0.01397 (10)	−0.00445 (10)	0.00694 (8)	0.00244 (9)
C5	0.0118 (10)	0.0193 (11)	0.0127 (10)	−0.0041 (8)	0.0037 (8)	−0.0012 (8)
Br5	0.02230 (12)	0.02245 (12)	0.02858 (13)	−0.00561 (10)	0.01408 (10)	−0.01180 (10)
C6	0.0099 (9)	0.0176 (10)	0.0126 (10)	−0.0019 (8)	0.0023 (8)	0.0002 (8)
F6	0.0148 (6)	0.0309 (8)	0.0135 (7)	0.0038 (7)	0.0017 (5)	0.0026 (6)
Br6	0.01599 (11)	0.01999 (12)	0.02962 (13)	−0.00840 (10)	0.00952 (9)	−0.00895 (10)
C7	0.0120 (10)	0.0205 (12)	0.0142 (10)	−0.0053 (8)	0.0041 (8)	0.0001 (8)
F7	0.0154 (7)	0.0339 (9)	0.0219 (8)	0.0074 (7)	0.0103 (6)	0.0043 (7)
Br7	0.01161 (10)	0.01818 (10)	0.01770 (11)	0.00211 (9)	0.00253 (8)	−0.00019 (9)
C8	0.0120 (10)	0.0191 (11)	0.0116 (10)	−0.0025 (8)	0.0047 (8)	0.0023 (8)
F8	0.0231 (8)	0.0395 (10)	0.0144 (7)	0.0028 (7)	0.0105 (6)	−0.0013 (6)
Br8	0.01666 (11)	0.02534 (12)	0.01741 (11)	0.00252 (9)	0.00493 (9)	−0.00738 (9)
C9	0.0100 (10)	0.0175 (10)	0.0128 (10)	−0.0026 (8)	0.0037 (8)	−0.0001 (8)
F9	0.0191 (7)	0.0417 (10)	0.0109 (7)	0.0042 (7)	−0.0004 (6)	0.0005 (7)
C10	0.0106 (9)	0.0192 (10)	0.0121 (10)	−0.0008 (8)	0.0035 (8)	0.0003 (8)
F10	0.0136 (6)	0.0366 (9)	0.0176 (7)	0.0075 (7)	0.0026 (5)	0.0001 (7)
C11	0.0114 (10)	0.0179 (11)	0.0119 (10)	−0.0016 (8)	0.0033 (8)	−0.0017 (8)
F11	0.0190 (7)	0.0339 (9)	0.0147 (7)	−0.0046 (7)	0.0046 (5)	0.0036 (7)
C12	0.0127 (10)	0.0191 (10)	0.0141 (10)	−0.0018 (8)	0.0049 (8)	−0.0044 (8)
F12	0.0194 (8)	0.0364 (9)	0.0186 (8)	−0.0014 (7)	−0.0059 (6)	0.0008 (7)
C13	0.0113 (10)	0.0174 (10)	0.0163 (11)	−0.0050 (8)	0.0037 (8)	−0.0035 (8)
F13	0.0092 (7)	0.0391 (10)	0.0436 (11)	−0.0090 (7)	−0.0015 (7)	0.0024 (8)
C14	0.0106 (9)	0.0178 (11)	0.0108 (10)	−0.0036 (8)	0.0029 (8)	−0.0016 (8)
F14	0.0167 (7)	0.0310 (9)	0.0364 (10)	−0.0066 (7)	0.0128 (7)	0.0085 (7)
C15	0.0100 (9)	0.0160 (10)	0.0117 (10)	−0.0029 (8)	0.0024 (7)	0.0003 (8)
F15	0.0187 (7)	0.0241 (7)	0.0160 (7)	−0.0034 (7)	0.0044 (5)	0.0046 (6)
C16	0.0094 (9)	0.0155 (10)	0.0132 (10)	−0.0019 (8)	0.0035 (8)	0.0008 (8)
F16	0.0387 (10)	0.0377 (10)	0.0246 (9)	−0.0199 (8)	0.0130 (8)	−0.0029 (8)
C17	0.0121 (10)	0.0155 (10)	0.0142 (10)	−0.0010 (8)	0.0043 (8)	0.0008 (8)
F17	0.0390 (11)	0.0824 (18)	0.0253 (9)	−0.0214 (12)	0.0179 (8)	0.0062 (10)
C18	0.0129 (10)	0.0165 (11)	0.0142 (10)	−0.0020 (8)	0.0061 (8)	−0.0021 (8)
F18	0.0316 (10)	0.0870 (17)	0.0141 (8)	0.0069 (11)	0.0110 (7)	−0.0063 (10)
C19	0.0115 (10)	0.0166 (10)	0.0119 (10)	−0.0015 (8)	0.0031 (8)	−0.0009 (8)
F19	0.0423 (11)	0.0587 (14)	0.0298 (10)	−0.0051 (10)	0.0096 (8)	−0.0288 (10)
C20	0.0130 (10)	0.0177 (10)	0.0114 (10)	−0.0029 (8)	0.0030 (8)	−0.0009 (8)
F20	0.0314 (9)	0.0332 (10)	0.0319 (9)	−0.0137 (8)	0.0119 (7)	−0.0134 (8)
N21	0.0085 (8)	0.0167 (9)	0.0105 (9)	−0.0010 (7)	0.0008 (7)	0.0010 (7)
N22	0.0103 (8)	0.0171 (9)	0.0109 (9)	−0.0028 (7)	0.0022 (7)	−0.0005 (7)
N23	0.0102 (8)	0.0179 (9)	0.0137 (9)	−0.0050 (7)	0.0048 (7)	−0.0047 (7)
Cl1S	0.0756 (12)	0.0204 (8)	0.0225 (8)	0.0033 (7)	0.0072 (7)	0.0020 (7)
F5	0.011 (4)	0.043 (2)	0.030 (5)	0.008 (4)	0.001 (3)	0.002 (3)
F4	0.0166 (13)	0.053 (3)	0.041 (2)	0.007 (2)	0.0093 (14)	0.006 (2)
F3	0.0136 (12)	0.066 (3)	0.0308 (14)	−0.014 (2)	−0.0003 (9)	0.008 (2)
F2	0.030 (2)	0.051 (3)	0.0291 (13)	−0.0231 (19)	0.0003 (16)	−0.007 (2)
F1	0.026 (4)	0.038 (4)	0.024 (4)	−0.012 (3)	0.001 (3)	−0.009 (2)
C1S	0.044 (2)	0.0133 (18)	0.0273 (15)	0.0029 (14)	0.0058 (15)	0.0024 (12)
Cl2S	0.0507 (7)	0.0301 (6)	0.0534 (9)	−0.0098 (5)	−0.0100 (6)	0.0206 (6)
Cl3S	0.0720 (11)	0.0283 (6)	0.0474 (8)	0.0150 (6)	0.0326 (8)	0.0138 (5)
N24	0.0100 (8)	0.0178 (9)	0.0117 (9)	−0.0008 (7)	0.0027 (7)	−0.0017 (7)
C51	0.0106 (10)	0.038 (2)	0.0130 (11)	−0.0062 (11)	0.0011 (9)	0.0038 (14)
C52	0.014 (2)	0.047 (3)	0.0141 (19)	−0.012 (2)	0.000 (2)	0.001 (2)
C53	0.019 (3)	0.051 (4)	0.0150 (13)	−0.016 (3)	0.0008 (19)	0.001 (3)
C54	0.0128 (14)	0.055 (4)	0.0175 (18)	−0.012 (3)	−0.0001 (13)	0.007 (3)
C55	0.0096 (16)	0.055 (4)	0.019 (3)	−0.004 (3)	0.0040 (17)	0.008 (3)
C56	0.0091 (19)	0.047 (3)	0.015 (3)	−0.0042 (16)	−0.0001 (16)	0.0050 (19)
C2S	0.044 (2)	0.0133 (18)	0.0273 (15)	0.0029 (14)	0.0058 (15)	0.0024 (12)
C51B	0.0106 (10)	0.038 (2)	0.0130 (11)	−0.0062 (11)	0.0011 (9)	0.0038 (14)
C52B	0.014 (2)	0.047 (3)	0.0141 (19)	−0.012 (2)	0.000 (2)	0.001 (2)
C53B	0.019 (3)	0.051 (4)	0.0150 (13)	−0.016 (3)	0.0008 (19)	0.001 (3)
C54B	0.0128 (14)	0.055 (4)	0.0175 (18)	−0.012 (3)	−0.0001 (13)	0.007 (3)
C55B	0.0096 (16)	0.055 (4)	0.019 (3)	−0.004 (3)	0.0040 (17)	0.008 (3)
C56B	0.0091 (19)	0.047 (3)	0.015 (3)	−0.0042 (16)	−0.0001 (16)	0.0050 (19)
F1B	0.026 (4)	0.038 (4)	0.024 (4)	−0.012 (3)	0.001 (3)	−0.009 (2)
F2B	0.030 (2)	0.051 (3)	0.0291 (13)	−0.0231 (19)	0.0003 (16)	−0.007 (2)
F3B	0.0136 (12)	0.066 (3)	0.0308 (14)	−0.014 (2)	−0.0003 (9)	0.008 (2)
F4B	0.0166 (13)	0.053 (3)	0.041 (2)	0.007 (2)	0.0093 (14)	0.006 (2)
F5B	0.011 (4)	0.043 (2)	0.030 (5)	0.008 (4)	0.001 (3)	0.002 (3)
C101	0.0109 (9)	0.0190 (10)	0.0118 (10)	−0.0015 (8)	0.0039 (8)	−0.0007 (8)
C102	0.0121 (10)	0.0187 (11)	0.0137 (10)	−0.0012 (8)	0.0036 (8)	0.0011 (8)
C103	0.0127 (10)	0.0203 (12)	0.0165 (11)	0.0011 (8)	0.0076 (8)	0.0024 (8)
C104	0.0187 (11)	0.0232 (11)	0.0139 (10)	−0.0010 (10)	0.0078 (8)	−0.0004 (10)
C105	0.0143 (11)	0.0254 (12)	0.0108 (10)	−0.0016 (9)	0.0017 (8)	0.0001 (9)
C106	0.0113 (10)	0.0204 (11)	0.0166 (11)	−0.0007 (8)	0.0047 (8)	−0.0004 (9)
C151	0.0095 (9)	0.0155 (10)	0.0134 (10)	−0.0018 (8)	0.0034 (8)	−0.0021 (8)
C152	0.0137 (10)	0.0190 (11)	0.0141 (10)	−0.0026 (9)	0.0036 (8)	−0.0008 (8)
C153	0.0146 (11)	0.0212 (12)	0.0178 (12)	0.0003 (9)	−0.0011 (9)	−0.0020 (9)
C154	0.0071 (9)	0.0209 (11)	0.0314 (13)	−0.0036 (9)	0.0003 (9)	−0.0004 (11)
C155	0.0119 (10)	0.0183 (12)	0.0284 (13)	−0.0023 (9)	0.0087 (9)	0.0030 (10)
C156	0.0129 (10)	0.0165 (11)	0.0161 (11)	−0.0003 (8)	0.0053 (8)	0.0005 (8)
C201	0.0119 (10)	0.0268 (12)	0.0109 (10)	−0.0014 (9)	0.0022 (8)	−0.0014 (9)
C202	0.0163 (11)	0.0328 (14)	0.0151 (11)	−0.0054 (10)	0.0040 (9)	0.0002 (10)
C203	0.0191 (13)	0.054 (2)	0.0155 (12)	−0.0046 (12)	0.0070 (10)	0.0053 (12)
C204	0.0180 (12)	0.063 (2)	0.0108 (11)	0.0059 (14)	0.0043 (9)	−0.0027 (13)
C205	0.0209 (13)	0.0445 (17)	0.0154 (12)	0.0019 (12)	0.0010 (10)	−0.0117 (12)
C206	0.0163 (11)	0.0303 (13)	0.0172 (12)	−0.0024 (10)	0.0045 (9)	−0.0051 (10)
Cl4S	0.123 (11)	0.048 (7)	0.037 (5)	0.045 (7)	0.024 (7)	0.015 (5)
Cl5S	0.052 (6)	0.044 (6)	0.097 (10)	−0.017 (5)	−0.003 (6)	0.036 (6)
Cl6S	0.075 (10)	0.025 (5)	0.032 (8)	−0.003 (7)	−0.015 (8)	−0.010 (6)

Geometric parameters (Å, º) top

C1—C2	1.442 (3)	F19—C205	1.339 (4)
C1—C20	1.394 (3)	C20—C201	1.484 (3)
C1—N21	1.371 (3)	F20—C206	1.336 (3)
Br1—C2	1.861 (2)	N21—H21	0.8800
C2—C3	1.368 (3)	N23—H23	0.8800
Br2—C3	1.862 (2)	Cl1S—C1S	1.755 (5)
C3—C4	1.439 (3)	F5—C56	1.30 (3)
Br3—C7	1.868 (2)	F4—C55	1.372 (13)
C4—C5	1.392 (3)	F3—C54	1.338 (11)
C4—N21	1.375 (3)	F2—C53	1.317 (11)
Br4—C8	1.862 (2)	F1—C52	1.32 (2)
C5—C6	1.414 (3)	C1S—H	1.0000
C5—C51	1.510 (9)	C1S—Cl2S	1.757 (5)
C5—C51B	1.504 (8)	C1S—Cl3S	1.760 (5)
Br5—C12	1.864 (2)	C51—C52	1.3900
C6—C7	1.467 (3)	C51—C56	1.3900
C6—N22	1.357 (3)	C52—C53	1.3900
F6—C102	1.339 (3)	C53—C54	1.3900
Br6—C13	1.862 (2)	C54—C55	1.3900
C7—C8	1.352 (3)	C55—C56	1.3900
F7—C103	1.340 (3)	C2S—HA	1.0000
Br7—C17	1.868 (2)	C2S—Cl4S	1.75 (3)
C8—C9	1.458 (3)	C2S—Cl5S	1.76 (3)
F8—C104	1.336 (3)	C2S—Cl6S	1.76 (3)
Br8—C18	1.867 (2)	C51B—C52B	1.3900
C9—C10	1.407 (3)	C51B—C56B	1.3900
C9—N22	1.366 (3)	C52B—C53B	1.3900
F9—C105	1.344 (3)	C52B—F1B	1.335 (16)
C10—C11	1.407 (3)	C53B—C54B	1.3900
C10—C101	1.484 (3)	C53B—F2B	1.366 (10)
F10—C106	1.343 (3)	C54B—C55B	1.3900
C11—C12	1.432 (3)	C54B—F3B	1.330 (9)
C11—N23	1.372 (3)	C55B—C56B	1.3900
F11—C152	1.336 (3)	C55B—F4B	1.312 (11)
C12—C13	1.371 (3)	C56B—F5B	1.34 (2)
F12—C153	1.344 (3)	C101—C102	1.392 (3)
C13—C14	1.430 (3)	C101—C106	1.395 (3)
F13—C154	1.335 (3)	C102—C103	1.384 (3)
C14—C15	1.412 (3)	C103—C104	1.379 (3)
C14—N23	1.372 (3)	C104—C105	1.380 (4)
F14—C155	1.337 (3)	C105—C106	1.378 (3)
C15—C16	1.405 (3)	C151—C152	1.397 (3)
C15—C151	1.484 (3)	C151—C156	1.395 (3)
F15—C156	1.331 (3)	C152—C153	1.383 (3)
C16—C17	1.460 (3)	C153—C154	1.380 (4)
C16—N24	1.374 (3)	C154—C155	1.378 (4)
F16—C202	1.336 (3)	C155—C156	1.389 (3)
C17—C18	1.354 (3)	C201—C202	1.389 (4)
F17—C203	1.338 (4)	C201—C206	1.391 (4)
C18—C19	1.456 (3)	C202—C203	1.385 (4)
F18—C204	1.336 (3)	C203—C204	1.369 (5)
C19—C20	1.420 (3)	C204—C205	1.385 (5)
C19—N24	1.358 (3)	C205—C206	1.378 (4)

C20—C1—C2	130.6 (2)	F3—C54—C55	121.0 (6)
N21—C1—C2	105.2 (2)	C55—C54—C53	120.0
N21—C1—C20	124.1 (2)	F4—C55—C54	117.6 (8)
C1—C2—Br1	127.12 (18)	F4—C55—C56	122.4 (8)
C3—C2—C1	108.4 (2)	C54—C55—C56	120.0
C3—C2—Br1	123.99 (19)	F5—C56—C51	122.3 (14)
C2—C3—Br2	123.52 (19)	F5—C56—C55	117.7 (14)
C2—C3—C4	108.6 (2)	C55—C56—C51	120.0
C4—C3—Br2	127.57 (19)	Cl4S—C2S—HA	114.7
C5—C4—C3	130.8 (2)	Cl4S—C2S—Cl5S	109 (2)
N21—C4—C3	105.2 (2)	Cl4S—C2S—Cl6S	102 (2)
N21—C4—C5	124.0 (2)	Cl5S—C2S—HA	114.7
C4—C5—C6	123.8 (2)	Cl6S—C2S—HA	114.7
C4—C5—C51	118.4 (10)	Cl6S—C2S—Cl5S	100 (2)
C4—C5—C51B	118.3 (8)	C52B—C51B—C5	118.1 (9)
C6—C5—C51	117.8 (10)	C52B—C51B—C56B	120.0
C6—C5—C51B	117.9 (8)	C56B—C51B—C5	121.9 (9)
C5—C6—C7	126.6 (2)	C53B—C52B—C51B	120.0
N22—C6—C5	122.6 (2)	F1B—C52B—C51B	123.4 (10)
N22—C6—C7	110.5 (2)	F1B—C52B—C53B	116.6 (10)
C6—C7—Br3	129.58 (18)	C52B—C53B—C54B	120.0
C8—C7—Br3	123.96 (18)	F2B—C53B—C52B	121.4 (6)
C8—C7—C6	106.0 (2)	F2B—C53B—C54B	118.6 (6)
C7—C8—Br4	125.40 (18)	C53B—C54B—C55B	120.0
C7—C8—C9	106.7 (2)	F3B—C54B—C53B	120.5 (5)
C9—C8—Br4	127.57 (18)	F3B—C54B—C55B	119.5 (5)
C10—C9—C8	126.2 (2)	C54B—C55B—C56B	120.0
N22—C9—C8	110.1 (2)	F4B—C55B—C54B	121.6 (6)
N22—C9—C10	122.9 (2)	F4B—C55B—C56B	118.4 (7)
C9—C10—C101	118.8 (2)	C55B—C56B—C51B	120.0
C11—C10—C9	123.0 (2)	F5B—C56B—C51B	120.0 (11)
C11—C10—C101	118.0 (2)	F5B—C56B—C55B	120.0 (11)
C10—C11—C12	131.3 (2)	C102—C101—C10	121.4 (2)
N23—C11—C10	123.0 (2)	C102—C101—C106	116.5 (2)
N23—C11—C12	105.6 (2)	C106—C101—C10	122.1 (2)
C11—C12—Br5	126.88 (18)	F6—C102—C101	119.9 (2)
C13—C12—Br5	124.21 (19)	F6—C102—C103	117.7 (2)
C13—C12—C11	108.3 (2)	C103—C102—C101	122.4 (2)
C12—C13—Br6	124.44 (19)	F7—C103—C102	120.7 (2)
C12—C13—C14	108.5 (2)	F7—C103—C104	120.0 (2)
C14—C13—Br6	126.40 (18)	C104—C103—C102	119.3 (2)
C15—C14—C13	131.5 (2)	F8—C104—C103	120.6 (2)
N23—C14—C13	105.6 (2)	F8—C104—C105	119.5 (2)
N23—C14—C15	122.9 (2)	C103—C104—C105	119.9 (2)
C14—C15—C151	117.8 (2)	F9—C105—C104	119.2 (2)
C16—C15—C14	121.8 (2)	F9—C105—C106	120.8 (2)
C16—C15—C151	120.4 (2)	C106—C105—C104	119.9 (2)
C15—C16—C17	127.5 (2)	F10—C106—C101	119.4 (2)
N24—C16—C15	122.1 (2)	F10—C106—C105	118.6 (2)
N24—C16—C17	110.2 (2)	C105—C106—C101	122.0 (2)
C16—C17—Br7	127.80 (18)	C152—C151—C15	121.6 (2)
C18—C17—Br7	125.52 (19)	C156—C151—C15	121.6 (2)
C18—C17—C16	106.3 (2)	C156—C151—C152	116.8 (2)
C17—C18—Br8	125.01 (18)	F11—C152—C151	120.2 (2)
C17—C18—C19	106.6 (2)	F11—C152—C153	118.1 (2)
C19—C18—Br8	127.61 (17)	C153—C152—C151	121.7 (2)
C20—C19—C18	126.2 (2)	F12—C153—C152	120.4 (2)
N24—C19—C18	110.6 (2)	F12—C153—C154	119.6 (2)
N24—C19—C20	123.0 (2)	C154—C153—C152	120.0 (2)
C1—C20—C19	123.4 (2)	F13—C154—C153	119.9 (2)
C1—C20—C201	119.6 (2)	F13—C154—C155	120.2 (2)
C19—C20—C201	117.0 (2)	C155—C154—C153	120.0 (2)
C1—N21—C4	112.39 (19)	F14—C155—C154	119.9 (2)
C1—N21—H21	123.8	F14—C155—C156	120.5 (2)
C4—N21—H21	123.8	C154—C155—C156	119.6 (2)
C6—N22—C9	106.16 (19)	F15—C156—C151	119.9 (2)
C11—N23—H23	124.1	F15—C156—C155	118.3 (2)
C14—N23—C11	111.9 (2)	C155—C156—C151	121.9 (2)
C14—N23—H23	124.1	C202—C201—C20	120.6 (2)
Cl1S—C1S—H	108.0	C202—C201—C206	116.6 (2)
Cl1S—C1S—Cl2S	111.8 (3)	C206—C201—C20	122.8 (2)
Cl1S—C1S—Cl3S	110.9 (3)	F16—C202—C201	119.9 (2)
Cl2S—C1S—H	108.0	F16—C202—C203	117.9 (3)
Cl2S—C1S—Cl3S	110.1 (3)	C203—C202—C201	122.2 (3)
Cl3S—C1S—H	108.0	F17—C203—C202	120.5 (3)
C19—N24—C16	105.90 (19)	F17—C203—C204	119.8 (3)
C52—C51—C5	122.6 (11)	C204—C203—C202	119.7 (3)
C52—C51—C56	120.0	F18—C204—C203	120.4 (3)
C56—C51—C5	117.4 (11)	F18—C204—C205	119.9 (3)
F1—C52—C51	119.4 (12)	C203—C204—C205	119.7 (3)
F1—C52—C53	120.5 (11)	F19—C205—C204	120.2 (3)
C53—C52—C51	120.0	F19—C205—C206	119.9 (3)
F2—C53—C52	118.4 (7)	C206—C205—C204	119.9 (3)
F2—C53—C54	121.6 (7)	F20—C206—C201	120.0 (2)
C52—C53—C54	120.0	F20—C206—C205	118.1 (3)
F3—C54—C53	118.9 (6)	C205—C206—C201	121.9 (3)

C1—C2—C3—Br2	−173.32 (18)	C18—C19—C20—C1	−158.9 (3)
C1—C2—C3—C4	0.3 (3)	C18—C19—C20—C201	22.2 (4)
C1—C20—C201—C202	−117.1 (3)	C18—C19—N24—C16	−6.5 (3)
C1—C20—C201—C206	64.9 (4)	F18—C204—C205—F19	−0.9 (5)
Br1—C2—C3—Br2	−0.6 (3)	F18—C204—C205—C206	179.6 (3)
Br1—C2—C3—C4	172.97 (18)	C19—C20—C201—C202	61.9 (3)
C2—C1—C20—C19	−169.3 (3)	C19—C20—C201—C206	−116.1 (3)
C2—C1—C20—C201	9.6 (4)	F19—C205—C206—F20	0.5 (4)
C2—C1—N21—C4	−5.1 (3)	F19—C205—C206—C201	−178.5 (3)
C2—C3—C4—C5	173.4 (3)	C20—C1—C2—Br1	14.5 (4)
C2—C3—C4—N21	−3.2 (3)	C20—C1—C2—C3	−173.1 (3)
Br2—C3—C4—C5	−13.4 (4)	C20—C1—N21—C4	171.1 (2)
Br2—C3—C4—N21	170.02 (19)	C20—C19—N24—C16	167.9 (2)
C3—C4—C5—C6	169.0 (3)	C20—C201—C202—F16	3.1 (4)
C3—C4—C5—C51	−9.0 (9)	C20—C201—C202—C203	−177.3 (3)
C3—C4—C5—C51B	−12.9 (8)	C20—C201—C206—F20	−2.4 (4)
C3—C4—N21—C1	5.2 (3)	C20—C201—C206—C205	176.7 (3)
Br3—C7—C8—Br4	−0.7 (3)	N21—C1—C2—Br1	−169.59 (18)
Br3—C7—C8—C9	−174.94 (18)	N21—C1—C2—C3	2.8 (3)
C4—C5—C6—C7	165.5 (2)	N21—C1—C20—C19	15.5 (4)
C4—C5—C6—N22	−21.1 (4)	N21—C1—C20—C201	−165.6 (2)
C4—C5—C51—C52	−68.3 (13)	N21—C4—C5—C6	−15.0 (4)
C4—C5—C51—C56	113.2 (9)	N21—C4—C5—C51	167.0 (8)
C4—C5—C51B—C52B	−69.1 (10)	N21—C4—C5—C51B	163.1 (7)
C4—C5—C51B—C56B	112.2 (8)	N22—C6—C7—Br3	169.45 (19)
Br4—C8—C9—C10	22.4 (4)	N22—C6—C7—C8	−2.7 (3)
Br4—C8—C9—N22	−167.51 (18)	N22—C9—C10—C11	22.5 (4)
C5—C4—N21—C1	−171.6 (2)	N22—C9—C10—C101	−153.4 (2)
C5—C6—C7—Br3	−16.5 (4)	N23—C11—C12—Br5	−168.58 (18)
C5—C6—C7—C8	171.4 (2)	N23—C11—C12—C13	2.6 (3)
C5—C6—N22—C9	−167.7 (2)	N23—C14—C15—C16	−25.9 (4)
C5—C51—C52—F1	3.7 (15)	N23—C14—C15—C151	155.8 (2)
C5—C51—C52—C53	−178.5 (18)	F4—C55—C56—F5	−4 (2)
C5—C51—C56—F5	−1.1 (18)	F4—C55—C56—C51	176.7 (13)
C5—C51—C56—C55	178.6 (17)	F3—C54—C55—F4	0.9 (14)
C5—C51B—C52B—C53B	−178.7 (15)	F3—C54—C55—C56	177.8 (12)
C5—C51B—C52B—F1B	1.0 (13)	F2—C53—C54—F3	2.1 (13)
C5—C51B—C56B—C55B	178.6 (15)	F2—C53—C54—C55	179.9 (13)
C5—C51B—C56B—F5B	−1.6 (15)	F1—C52—C53—F2	−2.1 (17)
Br5—C12—C13—Br6	0.4 (3)	F1—C52—C53—C54	177.8 (17)
Br5—C12—C13—C14	171.48 (18)	N24—C16—C17—Br7	169.92 (17)
C6—C5—C51—C52	113.6 (10)	N24—C16—C17—C18	−3.0 (3)
C6—C5—C51—C56	−64.9 (12)	N24—C19—C20—C1	27.6 (4)
C6—C5—C51B—C52B	109.1 (8)	N24—C19—C20—C201	−151.4 (2)
C6—C5—C51B—C56B	−69.6 (11)	C51—C5—C6—C7	−16.5 (9)
C6—C7—C8—Br4	171.98 (18)	C51—C5—C6—N22	156.9 (8)
C6—C7—C8—C9	−2.2 (3)	C51—C52—C53—F2	−179.9 (12)
F6—C102—C103—F7	−0.4 (4)	C51—C52—C53—C54	0.0
F6—C102—C103—C104	178.5 (2)	C52—C51—C56—F5	−180 (2)
Br6—C13—C14—C15	−14.4 (4)	C52—C51—C56—C55	0.0
Br6—C13—C14—N23	168.31 (18)	C52—C53—C54—F3	−177.8 (12)
C7—C6—N22—C9	6.7 (3)	C52—C53—C54—C55	0.0
C7—C8—C9—C10	−163.6 (2)	C53—C54—C55—F4	−176.9 (12)
C7—C8—C9—N22	6.5 (3)	C53—C54—C55—C56	0.0
F7—C103—C104—F8	1.7 (4)	C54—C55—C56—F5	180 (2)
F7—C103—C104—C105	−179.5 (2)	C54—C55—C56—C51	0.0
Br7—C17—C18—Br8	−3.3 (3)	C56—C51—C52—F1	−177.8 (17)
Br7—C17—C18—C19	−174.12 (17)	C56—C51—C52—C53	0.0
C8—C9—C10—C11	−168.6 (2)	C51B—C5—C6—C7	−12.6 (8)
C8—C9—C10—C101	15.5 (4)	C51B—C5—C6—N22	160.8 (7)
C8—C9—N22—C6	−8.1 (3)	C51B—C52B—C53B—C54B	0.0
F8—C104—C105—F9	−1.0 (4)	C51B—C52B—C53B—F2B	179.5 (10)
F8—C104—C105—C106	178.2 (2)	C52B—C51B—C56B—C55B	0.0
Br8—C18—C19—C20	20.1 (4)	C52B—C51B—C56B—F5B	179.8 (17)
Br8—C18—C19—N24	−165.68 (18)	C52B—C53B—C54B—C55B	0.0
C9—C10—C11—C12	−158.5 (3)	C52B—C53B—C54B—F3B	−178.1 (10)
C9—C10—C11—N23	25.2 (4)	C53B—C54B—C55B—C56B	0.0
C9—C10—C101—C102	54.8 (3)	C53B—C54B—C55B—F4B	−179.3 (11)
C9—C10—C101—C106	−125.1 (3)	C54B—C55B—C56B—C51B	0.0
F9—C105—C106—F10	−2.3 (4)	C54B—C55B—C56B—F5B	−179.8 (17)
F9—C105—C106—C101	178.6 (2)	C56B—C51B—C52B—C53B	0.0
C10—C9—N22—C6	162.4 (2)	C56B—C51B—C52B—F1B	179.6 (15)
C10—C11—C12—Br5	14.6 (4)	F1B—C52B—C53B—C54B	−179.7 (14)
C10—C11—C12—C13	−174.2 (3)	F1B—C52B—C53B—F2B	−0.2 (14)
C10—C11—N23—C14	172.7 (2)	F2B—C53B—C54B—C55B	−179.5 (10)
C10—C101—C102—F6	0.5 (4)	F2B—C53B—C54B—F3B	2.4 (11)
C10—C101—C102—C103	−179.3 (2)	F3B—C54B—C55B—C56B	178.1 (10)
C10—C101—C106—F10	1.5 (4)	F3B—C54B—C55B—F4B	−1.2 (12)
C10—C101—C106—C105	−179.5 (2)	F4B—C55B—C56B—C51B	179.3 (11)
C11—C10—C101—C102	−121.3 (3)	F4B—C55B—C56B—F5B	−0.5 (16)
C11—C10—C101—C106	58.8 (3)	C101—C10—C11—C12	17.4 (4)
C11—C12—C13—Br6	−171.15 (18)	C101—C10—C11—N23	−158.9 (2)
C11—C12—C13—C14	0.0 (3)	C101—C102—C103—F7	179.5 (2)
F11—C152—C153—F12	2.7 (4)	C101—C102—C103—C104	−1.7 (4)
F11—C152—C153—C154	−179.0 (2)	C102—C101—C106—F10	−178.4 (2)
C12—C11—N23—C14	−4.4 (3)	C102—C101—C106—C105	0.6 (4)
C12—C13—C14—C15	174.7 (3)	C102—C103—C104—F8	−177.1 (2)
C12—C13—C14—N23	−2.6 (3)	C102—C103—C104—C105	1.7 (4)
F12—C153—C154—F13	−0.6 (4)	C103—C104—C105—F9	−179.8 (2)
F12—C153—C154—C155	178.9 (3)	C103—C104—C105—C106	−0.5 (4)
C13—C14—C15—C16	157.2 (3)	C104—C105—C106—F10	178.4 (2)
C13—C14—C15—C151	−21.1 (4)	C104—C105—C106—C101	−0.6 (4)
C13—C14—N23—C11	4.4 (3)	C106—C101—C102—F6	−179.6 (2)
F13—C154—C155—F14	0.1 (4)	C106—C101—C102—C103	0.6 (4)
F13—C154—C155—C156	178.1 (2)	C151—C15—C16—C17	−18.9 (4)
C14—C15—C16—C17	162.8 (2)	C151—C15—C16—N24	154.5 (2)
C14—C15—C16—N24	−23.7 (4)	C151—C152—C153—F12	−177.4 (2)
C14—C15—C151—C152	−53.8 (3)	C151—C152—C153—C154	0.8 (4)
C14—C15—C151—C156	125.3 (3)	C152—C151—C156—F15	−179.7 (2)
F14—C155—C156—F15	−0.9 (4)	C152—C151—C156—C155	0.6 (4)
F14—C155—C156—C151	178.8 (2)	C152—C153—C154—F13	−178.9 (3)
C15—C14—N23—C11	−173.2 (2)	C152—C153—C154—C155	0.6 (4)
C15—C16—C17—Br7	−16.0 (4)	C153—C154—C155—F14	−179.4 (2)
C15—C16—C17—C18	171.1 (2)	C153—C154—C155—C156	−1.3 (4)
C15—C16—N24—C19	−168.6 (2)	C154—C155—C156—F15	−178.9 (2)
C15—C151—C152—F11	−2.5 (4)	C154—C155—C156—C151	0.7 (4)
C15—C151—C152—C153	177.7 (2)	C156—C151—C152—F11	178.4 (2)
C15—C151—C156—F15	1.2 (4)	C156—C151—C152—C153	−1.4 (4)
C15—C151—C156—C155	−178.5 (2)	C201—C202—C203—F17	−179.5 (3)
C16—C15—C151—C152	127.9 (3)	C201—C202—C203—C204	0.1 (5)
C16—C15—C151—C156	−53.1 (3)	C202—C201—C206—F20	179.6 (2)
C16—C17—C18—Br8	169.77 (17)	C202—C201—C206—C205	−1.4 (4)
C16—C17—C18—C19	−1.0 (3)	C202—C203—C204—F18	179.9 (3)
F16—C202—C203—F17	0.2 (4)	C202—C203—C204—C205	−0.5 (5)
F16—C202—C203—C204	179.8 (3)	C203—C204—C205—F19	179.5 (3)
C17—C16—N24—C19	5.9 (3)	C203—C204—C205—C206	−0.1 (5)
C17—C18—C19—C20	−169.4 (2)	C204—C205—C206—F20	−179.9 (3)
C17—C18—C19—N24	4.8 (3)	C204—C205—C206—C201	1.1 (5)
F17—C203—C204—F18	−0.5 (5)	C206—C201—C202—F16	−178.8 (2)
F17—C203—C204—C205	179.1 (3)	C206—C201—C202—C203	0.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21···N22	0.88	2.34	2.866 (3)	119
N21—H21···N24	0.88	2.42	2.928 (3)	117
N23—H23···N22	0.88	2.48	2.931 (3)	113
N23—H23···N24	0.88	2.46	2.895 (3)	111

2,3,7,8,12,13,17,18-Octabromo-5,10,15,20-tetrakis(pentafluorophenyl)porphyrin tetrahydrofuran monosolvate (1_THF) top

Crystal data top

C₄₄H₂Br₈F₂₀N₄·C₄H₈O	F(000) = 3176
M_r = 1677.88	D_x = 2.185 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 21.524 (9) Å	Cell parameters from 9873 reflections
b = 9.545 (4) Å	θ = 2.3–28.3°
c = 26.020 (11) Å	µ = 6.41 mm⁻¹
β = 107.426 (7)°	T = 100 K
V = 5101 (4) Å³	Block fragment, blue
Z = 4	0.42 × 0.11 × 0.09 mm

Data collection top

Bruker APEXII CCD diffractometer	12689 independent reflections
Radiation source: microfocus sealed X-ray tube, graphite-monochromated	10079 reflections with I > 2σ(I)
Mirror optics monochromator	R_int = 0.082
Detector resolution: 7.9 pixels mm^-1	θ_max = 28.3°, θ_min = 1.5°
φ and ω scans	h = −28→28
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −12→12
T_min = 0.455, T_max = 0.746	l = −34→34
148293 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.095	w = 1/[σ²(F_o²) + 36.9739P] where P = (F_o² + 2F_c²)/3
S = 1.21	(Δ/σ)_max = 0.001
12689 reflections	Δρ_max = 1.63 e Å⁻³
908 parameters	Δρ_min = −0.98 e Å⁻³
718 restraints

Special details top

Refinement. Two perfluoro rings were modelled as disordered over two locations with restraints (SADI, SIMU) and constraints (EXYZ, EADP for ipso carbons C12/C12a and C21/C21a) with occupancies of 75:25 and 70:30%. Pyrrole hydrogens located on the difference map and refined using restraints (DFIX). There is a short intermolecular HL..HL contact Br5···Br5 of 3.23 Angstroms (symmetry code = 1-x,-y,1-z = 3_656). See ALERT B

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Br1	0.52232 (2)	0.99320 (5)	0.17627 (2)	0.01967 (11)
Br2	0.65964 (2)	0.99488 (5)	0.28686 (2)	0.01897 (11)
Br3	0.82447 (2)	0.44087 (5)	0.35875 (2)	0.01795 (11)
Br4	0.77566 (3)	0.15494 (6)	0.41730 (2)	0.02278 (12)
Br5	0.49322 (3)	0.11413 (6)	0.45284 (2)	0.02566 (13)
Br6	0.35528 (3)	0.08167 (6)	0.34382 (2)	0.02386 (12)
Br7	0.35141 (3)	0.15311 (6)	0.10022 (2)	0.02311 (12)
Br8	0.39813 (3)	0.44804 (6)	0.04830 (2)	0.02922 (14)
F1B	0.3598 (14)	0.762 (2)	0.1217 (9)	0.024 (3)	0.306 (17)
F2B	0.3219 (10)	0.893 (2)	0.0271 (8)	0.034 (3)	0.306 (17)
F3B	0.4084 (10)	0.924 (2)	−0.0300 (7)	0.037 (3)	0.306 (17)
F4B	0.5320 (10)	0.819 (2)	0.0078 (7)	0.033 (3)	0.306 (17)
F5B	0.5669 (13)	0.674 (3)	0.1029 (10)	0.022 (3)	0.306 (17)
F6	0.73871 (14)	0.7001 (3)	0.23590 (11)	0.0205 (7)
F7	0.85729 (15)	0.8205 (3)	0.25703 (12)	0.0241 (7)
F8	0.92243 (15)	0.9035 (4)	0.35882 (14)	0.0313 (8)
F9	0.86678 (15)	0.8738 (3)	0.43919 (12)	0.0255 (7)
F10	0.75021 (15)	0.7465 (3)	0.41955 (11)	0.0222 (7)
F11B	0.6146 (14)	−0.081 (4)	0.3942 (12)	0.025 (3)	0.252 (18)
F12B	0.6698 (11)	−0.231 (3)	0.4832 (9)	0.030 (3)	0.252 (18)
F13B	0.7274 (11)	−0.093 (3)	0.5776 (9)	0.032 (3)	0.252 (18)
F14B	0.7159 (12)	0.188 (3)	0.5826 (10)	0.033 (3)	0.252 (18)
F15B	0.6587 (12)	0.339 (3)	0.4930 (12)	0.028 (3)	0.252 (18)
F16	0.40450 (15)	−0.0892 (3)	0.23781 (13)	0.0266 (7)
F17	0.28883 (18)	−0.2265 (4)	0.20717 (15)	0.0360 (9)
F18	0.17533 (17)	−0.0789 (4)	0.17611 (17)	0.0441 (10)
F19	0.17774 (15)	0.2053 (4)	0.17564 (16)	0.0395 (9)
F20	0.29175 (15)	0.3428 (3)	0.20559 (13)	0.0261 (7)
N21	0.57239 (19)	0.6076 (4)	0.25003 (16)	0.0150 (9)
N22	0.63177 (19)	0.4305 (4)	0.34616 (16)	0.0153 (9)
H22	0.5882 (12)	0.470 (5)	0.339 (2)	0.015 (14)*
N23	0.5165 (2)	0.2459 (4)	0.30937 (16)	0.0159 (9)
N24	0.4668 (2)	0.4152 (5)	0.21131 (16)	0.0163 (9)
H24	0.492 (2)	0.442 (6)	0.2476 (10)	0.032 (17)*
C1	0.4597 (2)	0.4950 (6)	0.16626 (19)	0.0154 (10)
C2	0.4854 (2)	0.6308 (5)	0.1660 (2)	0.0170 (10)
C3	0.5348 (2)	0.6877 (5)	0.2093 (2)	0.0164 (10)
C4	0.5587 (2)	0.8328 (5)	0.21547 (19)	0.0147 (10)
C5	0.6130 (2)	0.8340 (5)	0.2584 (2)	0.0150 (10)
C6	0.6230 (2)	0.6905 (5)	0.27870 (19)	0.0148 (10)
C7	0.6794 (2)	0.6364 (5)	0.31605 (19)	0.0149 (10)
C8	0.6838 (2)	0.5035 (5)	0.33991 (19)	0.0154 (10)
C9	0.7404 (2)	0.4180 (5)	0.36414 (19)	0.0143 (10)
C10	0.7210 (2)	0.3030 (5)	0.3861 (2)	0.0154 (10)
C11	0.6514 (2)	0.3098 (5)	0.37521 (19)	0.0158 (10)
C12	0.6088 (3)	0.2197 (5)	0.3909 (2)	0.0181 (11)
C12A	0.6362 (3)	0.1253 (6)	0.4380 (2)	0.0225 (9)	0.252 (18)
C12F	0.6624 (10)	0.1997 (13)	0.4855 (4)	0.0246 (15)	0.252 (18)
C12E	0.6914 (12)	0.129 (3)	0.5333 (3)	0.0259 (16)	0.252 (18)
C12D	0.6943 (11)	−0.017 (3)	0.5336 (6)	0.0258 (16)	0.252 (18)
C12C	0.6680 (13)	−0.0913 (13)	0.4861 (9)	0.0250 (16)	0.252 (18)
C12B	0.6390 (10)	−0.0202 (6)	0.4383 (6)	0.0234 (15)	0.252 (18)
C13	0.5419 (3)	0.2086 (5)	0.3621 (2)	0.0176 (10)
C14	0.4905 (2)	0.1467 (6)	0.38137 (18)	0.0166 (10)
C15	0.4364 (2)	0.1415 (6)	0.3390 (2)	0.0190 (11)
C16	0.4536 (2)	0.2014 (5)	0.29310 (19)	0.0145 (10)
C17	0.4142 (2)	0.2103 (5)	0.2392 (2)	0.0151 (10)
C18	0.4276 (2)	0.2986 (5)	0.2003 (2)	0.0159 (10)
C19	0.3984 (2)	0.2980 (5)	0.14292 (19)	0.0160 (10)
C20	0.4176 (2)	0.4162 (6)	0.12187 (19)	0.0175 (10)
C21B	0.4602 (3)	0.7128 (6)	0.1155 (2)	0.0194 (9)	0.306 (17)
C22B	0.4009 (18)	0.775 (4)	0.0944 (13)	0.0222 (16)	0.306 (17)
C23B	0.3830 (13)	0.846 (3)	0.0440 (11)	0.0258 (16)	0.306 (17)
C24B	0.4304 (15)	0.854 (3)	0.0173 (9)	0.0268 (16)	0.306 (17)
C25B	0.4895 (12)	0.802 (3)	0.0375 (11)	0.0259 (16)	0.306 (17)
C26B	0.5064 (16)	0.729 (4)	0.0845 (15)	0.0226 (15)	0.306 (17)
C71	0.7412 (2)	0.7171 (5)	0.3271 (2)	0.0149 (10)
C72	0.7695 (2)	0.7413 (5)	0.28649 (19)	0.0159 (10)
C73	0.8303 (2)	0.8037 (5)	0.2964 (2)	0.0175 (10)
C74	0.8631 (2)	0.8463 (5)	0.3483 (2)	0.0195 (11)
C75	0.8353 (2)	0.8286 (5)	0.3890 (2)	0.0176 (10)
C76	0.7754 (2)	0.7640 (5)	0.3785 (2)	0.0177 (10)
C171	0.3519 (2)	0.1309 (6)	0.22187 (19)	0.0165 (10)
C172	0.3489 (3)	−0.0143 (6)	0.2218 (2)	0.0210 (11)
C173	0.2904 (3)	−0.0867 (6)	0.2065 (2)	0.0271 (13)
C174	0.2327 (3)	−0.0110 (7)	0.1905 (3)	0.0315 (14)
C175	0.2339 (3)	0.1325 (6)	0.1905 (2)	0.0252 (12)
C176	0.2929 (3)	0.2012 (6)	0.2059 (2)	0.0207 (11)
F1A	0.3574 (5)	0.7361 (10)	0.1329 (4)	0.0236 (17)	0.694 (17)
F2A	0.3068 (4)	0.8801 (10)	0.0399 (4)	0.0346 (19)	0.694 (17)
F3A	0.3808 (5)	0.9315 (9)	−0.0262 (3)	0.0399 (19)	0.694 (17)
F4A	0.5055 (5)	0.8370 (9)	0.0000 (3)	0.0370 (17)	0.694 (17)
F5A	0.5569 (6)	0.6956 (12)	0.0924 (4)	0.0267 (18)	0.694 (17)
F11A	0.6002 (5)	−0.0773 (12)	0.3832 (4)	0.0261 (16)	0.748 (18)
F12A	0.6504 (4)	−0.2514 (7)	0.4669 (4)	0.0321 (15)	0.748 (18)
F13A	0.7155 (4)	−0.1454 (10)	0.5655 (3)	0.0349 (16)	0.748 (18)
F14A	0.7237 (4)	0.1351 (10)	0.5815 (3)	0.0362 (16)	0.748 (18)
F15A	0.6742 (4)	0.3116 (9)	0.4979 (4)	0.0303 (16)	0.748 (18)
O25	0.5156 (2)	0.5565 (5)	0.3555 (2)	0.0452 (12)
C26	0.4822 (3)	0.6868 (7)	0.3386 (3)	0.0428 (17)
H26A	0.440036	0.670382	0.310628	0.051*
H26B	0.508874	0.750268	0.323698	0.051*
C27	0.4714 (3)	0.7495 (8)	0.3890 (3)	0.0485 (19)
H27A	0.431987	0.809281	0.379803	0.058*
H27B	0.509394	0.805839	0.409327	0.058*
C28	0.4628 (4)	0.6212 (8)	0.4209 (3)	0.0492 (19)
H28A	0.476700	0.640698	0.460102	0.059*
H28B	0.417027	0.588821	0.409734	0.059*
C29	0.5061 (5)	0.5173 (9)	0.4068 (4)	0.073 (3)
H29A	0.548620	0.514797	0.435283	0.088*
H29B	0.486356	0.422913	0.403966	0.088*
C21A	0.4602 (3)	0.7128 (6)	0.1155 (2)	0.0194 (9)	0.694 (17)
C22A	0.3956 (8)	0.7599 (15)	0.1009 (5)	0.0214 (15)	0.694 (17)
C23A	0.3688 (5)	0.8339 (11)	0.0536 (4)	0.0242 (15)	0.694 (17)
C24A	0.4061 (6)	0.8611 (11)	0.0197 (4)	0.0271 (15)	0.694 (17)
C25A	0.4697 (6)	0.8157 (12)	0.0333 (4)	0.0258 (14)	0.694 (17)
C26A	0.4955 (6)	0.7428 (16)	0.0809 (6)	0.0227 (14)	0.694 (17)
C121	0.6362 (3)	0.1253 (6)	0.4380 (2)	0.0225 (9)	0.748 (18)
C122	0.6306 (4)	−0.0197 (8)	0.4319 (3)	0.0222 (11)	0.748 (18)
C123	0.6566 (5)	−0.1134 (9)	0.4740 (4)	0.0253 (12)	0.748 (18)
C124	0.6892 (4)	−0.0585 (11)	0.5241 (4)	0.0253 (13)	0.748 (18)
C125	0.6943 (5)	0.0823 (12)	0.5328 (3)	0.0255 (13)	0.748 (18)
C126	0.6682 (4)	0.1736 (10)	0.4902 (3)	0.0240 (12)	0.748 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0205 (2)	0.0128 (2)	0.0221 (3)	0.0018 (2)	0.00074 (19)	0.0039 (2)
Br2	0.0225 (2)	0.0116 (2)	0.0198 (2)	−0.0023 (2)	0.00176 (19)	−0.0003 (2)
Br3	0.0163 (2)	0.0166 (2)	0.0195 (2)	0.0006 (2)	0.00298 (19)	−0.0003 (2)
Br4	0.0204 (3)	0.0165 (3)	0.0274 (3)	0.0033 (2)	0.0011 (2)	0.0070 (2)
Br5	0.0309 (3)	0.0302 (3)	0.0177 (3)	−0.0009 (2)	0.0100 (2)	0.0056 (2)
Br6	0.0197 (3)	0.0276 (3)	0.0268 (3)	−0.0009 (2)	0.0107 (2)	0.0072 (2)
Br7	0.0259 (3)	0.0183 (3)	0.0216 (3)	−0.0048 (2)	0.0017 (2)	−0.0021 (2)
Br8	0.0433 (3)	0.0249 (3)	0.0145 (2)	−0.0085 (3)	0.0011 (2)	0.0009 (2)
F1B	0.024 (4)	0.021 (5)	0.022 (5)	0.004 (4)	−0.001 (5)	0.008 (4)
F2B	0.037 (5)	0.022 (4)	0.029 (5)	0.001 (4)	−0.012 (4)	0.006 (4)
F3B	0.048 (6)	0.028 (5)	0.022 (4)	−0.002 (6)	−0.008 (5)	0.009 (4)
F4B	0.044 (6)	0.032 (5)	0.021 (5)	−0.007 (5)	0.007 (5)	0.010 (4)
F5B	0.027 (6)	0.022 (6)	0.018 (6)	−0.001 (5)	0.008 (5)	0.011 (5)
F6	0.0234 (16)	0.0227 (17)	0.0141 (14)	−0.0004 (13)	0.0034 (12)	−0.0023 (12)
F7	0.0283 (17)	0.0228 (17)	0.0242 (16)	−0.0036 (14)	0.0126 (13)	0.0019 (14)
F8	0.0222 (16)	0.033 (2)	0.0364 (19)	−0.0134 (15)	0.0055 (14)	−0.0040 (16)
F9	0.0270 (17)	0.0245 (18)	0.0193 (15)	−0.0054 (14)	−0.0019 (13)	−0.0059 (13)
F10	0.0260 (16)	0.0264 (17)	0.0151 (15)	−0.0026 (14)	0.0073 (12)	−0.0020 (13)
F11B	0.022 (6)	0.025 (5)	0.026 (6)	0.000 (5)	0.002 (5)	0.010 (5)
F12B	0.030 (5)	0.030 (5)	0.031 (5)	0.008 (5)	0.008 (4)	0.015 (5)
F13B	0.028 (5)	0.039 (6)	0.028 (5)	0.013 (5)	0.008 (4)	0.019 (5)
F14B	0.034 (5)	0.041 (6)	0.019 (5)	0.003 (6)	−0.001 (4)	0.008 (6)
F15B	0.025 (6)	0.031 (6)	0.024 (5)	0.002 (5)	−0.001 (5)	0.003 (5)
F16	0.0236 (16)	0.0167 (17)	0.0383 (19)	0.0016 (13)	0.0075 (14)	0.0057 (14)
F17	0.040 (2)	0.0193 (18)	0.049 (2)	−0.0109 (16)	0.0139 (18)	−0.0005 (16)
F18	0.0234 (18)	0.040 (2)	0.064 (3)	−0.0194 (17)	0.0056 (17)	−0.002 (2)
F19	0.0142 (16)	0.042 (2)	0.058 (2)	0.0033 (15)	0.0050 (16)	0.0043 (19)
F20	0.0218 (16)	0.0203 (17)	0.0354 (19)	0.0020 (13)	0.0074 (14)	0.0020 (14)
N21	0.015 (2)	0.014 (2)	0.014 (2)	−0.0024 (17)	0.0015 (16)	0.0022 (17)
N22	0.013 (2)	0.013 (2)	0.018 (2)	−0.0050 (17)	0.0025 (16)	0.0034 (17)
N23	0.016 (2)	0.016 (2)	0.014 (2)	−0.0011 (17)	0.0011 (16)	0.0026 (17)
N24	0.018 (2)	0.018 (2)	0.0109 (19)	−0.0022 (18)	0.0011 (16)	0.0020 (17)
C1	0.015 (2)	0.016 (2)	0.014 (2)	0.004 (2)	0.0034 (18)	0.003 (2)
C2	0.017 (2)	0.018 (3)	0.014 (2)	0.003 (2)	0.0029 (19)	0.003 (2)
C3	0.015 (2)	0.016 (3)	0.017 (2)	−0.001 (2)	0.0032 (19)	0.004 (2)
C4	0.015 (2)	0.013 (2)	0.017 (2)	0.0019 (19)	0.0045 (19)	0.003 (2)
C5	0.018 (2)	0.009 (2)	0.017 (2)	0.0016 (19)	0.0039 (19)	0.0008 (19)
C6	0.015 (2)	0.016 (3)	0.014 (2)	0.0005 (19)	0.0052 (19)	0.0027 (19)
C7	0.019 (2)	0.011 (2)	0.013 (2)	0.0016 (19)	0.0036 (19)	−0.0010 (19)
C8	0.017 (2)	0.015 (2)	0.012 (2)	−0.002 (2)	0.0022 (18)	0.000 (2)
C9	0.015 (2)	0.012 (2)	0.014 (2)	0.0000 (19)	0.0006 (18)	−0.0020 (19)
C10	0.017 (2)	0.011 (2)	0.016 (2)	0.0024 (19)	0.0005 (19)	0.0025 (19)
C11	0.020 (2)	0.013 (2)	0.012 (2)	0.000 (2)	0.0015 (19)	0.0008 (19)
C12	0.024 (3)	0.015 (3)	0.014 (2)	−0.001 (2)	0.004 (2)	0.002 (2)
C12A	0.0202 (17)	0.0260 (18)	0.0209 (17)	−0.0001 (16)	0.0055 (15)	0.0079 (16)
C12F	0.023 (3)	0.028 (3)	0.021 (2)	0.000 (3)	0.004 (2)	0.009 (2)
C12E	0.025 (2)	0.030 (3)	0.021 (2)	0.001 (3)	0.005 (2)	0.010 (3)
C12D	0.024 (2)	0.030 (3)	0.023 (3)	0.004 (3)	0.007 (2)	0.011 (3)
C12C	0.023 (3)	0.027 (3)	0.025 (3)	0.004 (2)	0.008 (2)	0.010 (3)
C12B	0.021 (3)	0.026 (3)	0.023 (3)	0.002 (2)	0.007 (2)	0.008 (2)
C13	0.024 (3)	0.012 (2)	0.016 (2)	−0.002 (2)	0.006 (2)	0.002 (2)
C14	0.024 (3)	0.019 (3)	0.007 (2)	0.000 (2)	0.0043 (19)	0.0037 (19)
C15	0.018 (2)	0.015 (3)	0.025 (3)	−0.003 (2)	0.008 (2)	0.002 (2)
C16	0.017 (2)	0.010 (2)	0.016 (2)	−0.0008 (19)	0.0046 (19)	0.0028 (19)
C17	0.013 (2)	0.015 (2)	0.017 (2)	0.0013 (19)	0.0045 (19)	0.002 (2)
C18	0.013 (2)	0.014 (2)	0.019 (2)	0.0030 (19)	0.0004 (19)	0.002 (2)
C19	0.016 (2)	0.018 (3)	0.014 (2)	0.000 (2)	0.0031 (19)	−0.001 (2)
C20	0.019 (2)	0.019 (3)	0.011 (2)	0.002 (2)	0.0000 (19)	0.002 (2)
C21B	0.0267 (19)	0.0146 (17)	0.0141 (17)	−0.0026 (16)	0.0018 (15)	0.0026 (15)
C22B	0.029 (3)	0.016 (3)	0.017 (3)	−0.001 (2)	0.000 (2)	0.003 (2)
C23B	0.032 (3)	0.019 (2)	0.019 (2)	−0.002 (2)	−0.003 (2)	0.005 (2)
C24B	0.035 (3)	0.020 (2)	0.019 (2)	−0.003 (3)	−0.001 (3)	0.005 (2)
C25B	0.034 (3)	0.021 (3)	0.019 (2)	−0.003 (3)	0.001 (3)	0.005 (2)
C26B	0.030 (3)	0.018 (3)	0.017 (2)	−0.003 (3)	0.002 (3)	0.005 (2)
C71	0.018 (2)	0.006 (2)	0.017 (2)	−0.0018 (19)	0.0010 (19)	0.0012 (19)
C72	0.020 (2)	0.011 (2)	0.014 (2)	0.002 (2)	0.0007 (19)	−0.0003 (19)
C73	0.020 (3)	0.012 (2)	0.022 (3)	0.001 (2)	0.009 (2)	0.003 (2)
C74	0.016 (2)	0.010 (2)	0.029 (3)	−0.003 (2)	0.003 (2)	−0.001 (2)
C75	0.019 (2)	0.013 (2)	0.017 (2)	−0.002 (2)	−0.001 (2)	−0.003 (2)
C76	0.021 (3)	0.013 (3)	0.019 (3)	0.003 (2)	0.005 (2)	0.000 (2)
C171	0.019 (2)	0.018 (3)	0.013 (2)	−0.002 (2)	0.0061 (19)	0.001 (2)
C172	0.020 (3)	0.019 (3)	0.024 (3)	−0.001 (2)	0.006 (2)	0.003 (2)
C173	0.030 (3)	0.020 (3)	0.032 (3)	−0.011 (2)	0.011 (3)	−0.004 (2)
C174	0.019 (3)	0.035 (4)	0.038 (3)	−0.014 (3)	0.005 (2)	0.000 (3)
C175	0.017 (3)	0.028 (3)	0.030 (3)	−0.001 (2)	0.006 (2)	0.002 (3)
C176	0.022 (3)	0.020 (3)	0.020 (3)	−0.003 (2)	0.006 (2)	0.000 (2)
F1A	0.022 (2)	0.021 (4)	0.027 (4)	0.004 (3)	0.006 (3)	0.009 (3)
F2A	0.030 (4)	0.027 (3)	0.033 (4)	0.002 (3)	−0.010 (3)	0.008 (3)
F3A	0.051 (4)	0.032 (3)	0.023 (3)	−0.001 (3)	−0.010 (3)	0.013 (2)
F4A	0.048 (4)	0.038 (3)	0.024 (3)	−0.008 (3)	0.010 (3)	0.008 (2)
F5A	0.031 (4)	0.029 (4)	0.022 (4)	−0.001 (3)	0.011 (3)	0.009 (3)
F11A	0.028 (4)	0.022 (2)	0.025 (4)	−0.002 (3)	0.003 (3)	0.002 (3)
F12A	0.036 (4)	0.022 (3)	0.041 (4)	0.006 (2)	0.015 (3)	0.015 (3)
F13A	0.033 (3)	0.041 (4)	0.030 (3)	0.010 (3)	0.009 (2)	0.020 (3)
F14A	0.036 (3)	0.044 (4)	0.021 (2)	−0.003 (3)	−0.003 (2)	0.008 (3)
F15A	0.034 (4)	0.028 (3)	0.021 (3)	−0.002 (3)	−0.004 (3)	0.003 (2)
O25	0.044 (3)	0.029 (3)	0.072 (4)	0.013 (2)	0.031 (3)	0.010 (2)
C26	0.031 (4)	0.029 (4)	0.068 (5)	0.009 (3)	0.015 (3)	0.007 (3)
C27	0.032 (4)	0.040 (4)	0.075 (5)	−0.001 (3)	0.018 (4)	−0.012 (4)
C28	0.051 (5)	0.042 (4)	0.055 (5)	0.012 (4)	0.017 (4)	−0.001 (4)
C29	0.112 (8)	0.040 (5)	0.090 (7)	0.039 (5)	0.064 (6)	0.023 (5)
C21A	0.0267 (19)	0.0146 (17)	0.0141 (17)	−0.0026 (16)	0.0018 (15)	0.0026 (15)
C22A	0.028 (3)	0.016 (2)	0.016 (3)	−0.002 (2)	0.000 (2)	0.003 (2)
C23A	0.031 (3)	0.017 (2)	0.018 (2)	−0.001 (2)	−0.003 (2)	0.003 (2)
C24A	0.035 (3)	0.019 (2)	0.020 (2)	−0.003 (2)	−0.003 (2)	0.005 (2)
C25A	0.034 (3)	0.021 (2)	0.019 (2)	−0.004 (2)	0.001 (2)	0.005 (2)
C26A	0.029 (3)	0.018 (2)	0.018 (2)	−0.003 (2)	0.002 (2)	0.003 (2)
C121	0.0202 (17)	0.0260 (18)	0.0209 (17)	−0.0001 (16)	0.0055 (15)	0.0079 (16)
C122	0.020 (2)	0.025 (2)	0.022 (2)	0.0027 (19)	0.0075 (19)	0.009 (2)
C123	0.023 (2)	0.027 (2)	0.027 (2)	0.004 (2)	0.009 (2)	0.009 (2)
C124	0.023 (2)	0.030 (3)	0.023 (2)	0.005 (2)	0.0083 (19)	0.012 (2)
C125	0.024 (2)	0.030 (3)	0.021 (2)	0.000 (2)	0.0046 (18)	0.009 (2)
C126	0.023 (2)	0.027 (2)	0.021 (2)	0.000 (2)	0.0042 (18)	0.008 (2)

Geometric parameters (Å, º) top

Br1—C4	1.876 (5)	C13—C14	1.468 (7)
Br2—C5	1.862 (5)	C14—C15	1.343 (7)
Br3—C9	1.869 (5)	C15—C16	1.468 (7)
Br4—C10	1.863 (5)	C16—C17	1.408 (7)
Br5—C14	1.869 (5)	C17—C18	1.411 (7)
Br6—C15	1.877 (5)	C17—C171	1.488 (7)
Br7—C19	1.870 (5)	C18—C19	1.437 (7)
Br8—C20	1.858 (5)	C19—C20	1.370 (7)
F1B—C22B	1.30 (4)	C21B—C22B	1.37 (4)
F2B—C23B	1.33 (3)	C21B—C26B	1.46 (4)
F3B—C24B	1.35 (3)	C22B—C23B	1.42 (3)
F4B—C25B	1.37 (3)	C23B—C24B	1.40 (3)
F5B—C26B	1.35 (3)	C24B—C25B	1.32 (3)
F6—C72	1.343 (5)	C25B—C26B	1.36 (4)
F7—C73	1.329 (6)	C71—C72	1.389 (7)
F8—C74	1.339 (6)	C71—C76	1.392 (7)
F9—C75	1.350 (5)	C72—C73	1.389 (7)
F10—C76	1.346 (6)	C73—C74	1.386 (7)
F11B—C12B	1.25 (3)	C74—C75	1.373 (8)
F12B—C12C	1.34 (2)	C75—C76	1.380 (7)
F13B—C12D	1.36 (2)	C171—C172	1.388 (7)
F14B—C12E	1.36 (3)	C171—C176	1.385 (7)
F15B—C12F	1.35 (3)	C172—C173	1.385 (7)
F16—C172	1.349 (6)	C173—C174	1.390 (9)
F17—C173	1.335 (7)	C174—C175	1.370 (9)
F18—C174	1.344 (6)	C175—C176	1.378 (7)
F19—C175	1.346 (6)	F1A—C22A	1.354 (15)
F20—C176	1.352 (6)	F2A—C23A	1.348 (12)
N21—C3	1.358 (6)	F3A—C24A	1.334 (12)
N21—C6	1.371 (6)	F4A—C25A	1.337 (13)
N22—H22	0.974 (10)	F5A—C26A	1.344 (15)
N22—C8	1.369 (6)	F11A—C122	1.356 (12)
N22—C11	1.373 (6)	F12A—C123	1.331 (11)
N23—C13	1.363 (6)	F13A—C124	1.343 (9)
N23—C16	1.361 (6)	F14A—C125	1.334 (11)
N24—H24	0.975 (10)	F15A—C126	1.333 (11)
N24—C1	1.368 (6)	O25—C26	1.439 (8)
N24—C18	1.374 (6)	O25—C29	1.459 (9)
C1—C2	1.410 (7)	C26—H26A	0.9900
C1—C20	1.448 (7)	C26—H26B	0.9900
C2—C3	1.407 (7)	C26—C27	1.521 (10)
C2—C21B	1.487 (7)	C27—H27A	0.9900
C2—C21A	1.487 (7)	C27—H27B	0.9900
C3—C4	1.469 (7)	C27—C28	1.522 (11)
C4—C5	1.354 (7)	C28—H28A	0.9900
C5—C6	1.461 (7)	C28—H28B	0.9900
C6—C7	1.407 (7)	C28—C29	1.481 (10)
C7—C8	1.403 (7)	C29—H29A	0.9900
C7—C71	1.490 (7)	C29—H29B	0.9900
C8—C9	1.446 (7)	C21A—C22A	1.400 (18)
C9—C10	1.361 (7)	C21A—C26A	1.370 (19)
C10—C11	1.440 (7)	C22A—C23A	1.385 (15)
C11—C12	1.404 (7)	C23A—C24A	1.385 (14)
C12—C12A	1.493 (7)	C24A—C25A	1.377 (13)
C12—C13	1.414 (7)	C25A—C26A	1.384 (16)
C12—C121	1.493 (7)	C121—C122	1.395 (11)
C12A—C12F	1.3900	C121—C126	1.405 (10)
C12A—C12B	1.3900	C122—C123	1.396 (10)
C12F—C12E	1.3900	C123—C124	1.385 (11)
C12E—C12D	1.3900	C124—C125	1.362 (12)
C12D—C12C	1.3900	C125—C126	1.389 (11)
C12C—C12B	1.3900

C3—N21—C6	106.8 (4)	C24B—C25B—C26B	121 (3)
C8—N22—H22	124 (3)	C26B—C25B—F4B	122 (2)
C8—N22—C11	111.4 (4)	F5B—C26B—C21B	120 (3)
C11—N22—H22	123 (3)	F5B—C26B—C25B	119 (3)
C16—N23—C13	107.0 (4)	C25B—C26B—C21B	120 (2)
C1—N24—H24	125 (4)	C72—C71—C7	120.6 (4)
C1—N24—C18	111.7 (4)	C72—C71—C76	116.8 (5)
C18—N24—H24	123 (4)	C76—C71—C7	122.5 (5)
N24—C1—C2	124.9 (5)	F6—C72—C71	119.8 (4)
N24—C1—C20	106.1 (4)	F6—C72—C73	117.9 (4)
C2—C1—C20	128.9 (5)	C73—C72—C71	122.3 (5)
C1—C2—C21B	116.6 (4)	F7—C73—C72	120.9 (5)
C1—C2—C21A	116.6 (4)	F7—C73—C74	120.2 (5)
C3—C2—C1	123.7 (5)	C74—C73—C72	118.9 (5)
C3—C2—C21B	119.6 (5)	F8—C74—C73	119.7 (5)
C3—C2—C21A	119.6 (5)	F8—C74—C75	120.2 (5)
N21—C3—C2	122.5 (5)	C75—C74—C73	120.2 (5)
N21—C3—C4	109.8 (4)	F9—C75—C74	119.8 (4)
C2—C3—C4	127.3 (5)	F9—C75—C76	120.2 (5)
C3—C4—Br1	129.5 (4)	C74—C75—C76	119.9 (5)
C5—C4—Br1	123.9 (4)	F10—C76—C71	120.0 (5)
C5—C4—C3	106.6 (4)	F10—C76—C75	118.2 (4)
C4—C5—Br2	124.4 (4)	C75—C76—C71	121.9 (5)
C4—C5—C6	106.7 (4)	C172—C171—C17	123.1 (5)
C6—C5—Br2	128.8 (4)	C176—C171—C17	120.4 (5)
N21—C6—C5	109.7 (4)	C176—C171—C172	116.5 (5)
N21—C6—C7	123.0 (5)	F16—C172—C171	119.5 (5)
C7—C6—C5	126.7 (5)	F16—C172—C173	118.0 (5)
C6—C7—C71	118.7 (4)	C173—C172—C171	122.4 (5)
C8—C7—C6	124.6 (5)	F17—C173—C172	121.3 (5)
C8—C7—C71	116.3 (4)	F17—C173—C174	120.0 (5)
N22—C8—C7	124.3 (5)	C172—C173—C174	118.7 (5)
N22—C8—C9	105.9 (4)	F18—C174—C173	119.8 (6)
C7—C8—C9	129.8 (5)	F18—C174—C175	119.9 (6)
C8—C9—Br3	127.6 (4)	C175—C174—C173	120.3 (5)
C10—C9—Br3	123.6 (4)	F19—C175—C174	120.0 (5)
C10—C9—C8	108.2 (4)	F19—C175—C176	120.5 (5)
C9—C10—Br4	124.1 (4)	C174—C175—C176	119.5 (5)
C9—C10—C11	108.3 (4)	F20—C176—C171	120.0 (5)
C11—C10—Br4	127.2 (4)	F20—C176—C175	117.4 (5)
N22—C11—C10	106.0 (4)	C175—C176—C171	122.6 (5)
N22—C11—C12	123.7 (5)	C26—O25—C29	107.9 (5)
C12—C11—C10	130.3 (5)	O25—C26—H26A	110.6
C11—C12—C12A	118.4 (5)	O25—C26—H26B	110.6
C11—C12—C13	122.8 (5)	O25—C26—C27	105.5 (6)
C11—C12—C121	118.4 (5)	H26A—C26—H26B	108.8
C13—C12—C12A	118.6 (5)	C27—C26—H26A	110.6
C13—C12—C121	118.6 (5)	C27—C26—H26B	110.6
C12F—C12A—C12	112.2 (7)	C26—C27—H27A	111.1
C12F—C12A—C12B	120.0	C26—C27—H27B	111.1
C12B—C12A—C12	127.8 (7)	C26—C27—C28	103.3 (6)
F15B—C12F—C12A	127.2 (14)	H27A—C27—H27B	109.1
F15B—C12F—C12E	112.5 (14)	C28—C27—H27A	111.1
C12E—C12F—C12A	120.0	C28—C27—H27B	111.1
F14B—C12E—C12F	125.8 (14)	C27—C28—H28A	111.3
F14B—C12E—C12D	114.2 (14)	C27—C28—H28B	111.3
C12F—C12E—C12D	120.0	H28A—C28—H28B	109.2
F13B—C12D—C12E	123.0 (15)	C29—C28—C27	102.4 (6)
F13B—C12D—C12C	116.7 (15)	C29—C28—H28A	111.3
C12E—C12D—C12C	120.0	C29—C28—H28B	111.3
F12B—C12C—C12D	123.2 (14)	O25—C29—C28	109.1 (6)
F12B—C12C—C12B	116.8 (14)	O25—C29—H29A	109.9
C12B—C12C—C12D	120.0	O25—C29—H29B	109.9
F11B—C12B—C12A	116.8 (18)	C28—C29—H29A	109.9
F11B—C12B—C12C	123.2 (18)	C28—C29—H29B	109.9
C12C—C12B—C12A	120.0	H29A—C29—H29B	108.3
N23—C13—C12	123.4 (5)	C22A—C21A—C2	118.6 (6)
N23—C13—C14	109.5 (4)	C26A—C21A—C2	124.3 (6)
C12—C13—C14	126.9 (5)	C26A—C21A—C22A	117.1 (7)
C13—C14—Br5	127.2 (4)	F1A—C22A—C21A	121.1 (9)
C15—C14—Br5	124.8 (4)	F1A—C22A—C23A	117.6 (13)
C15—C14—C13	106.9 (4)	C23A—C22A—C21A	121.3 (10)
C14—C15—Br6	123.5 (4)	F2A—C23A—C22A	121.3 (10)
C14—C15—C16	106.6 (4)	F2A—C23A—C24A	119.1 (8)
C16—C15—Br6	129.7 (4)	C24A—C23A—C22A	119.7 (10)
N23—C16—C15	109.8 (4)	F3A—C24A—C23A	120.4 (9)
N23—C16—C17	122.5 (4)	F3A—C24A—C25A	119.7 (10)
C17—C16—C15	127.7 (4)	C25A—C24A—C23A	119.9 (9)
C16—C17—C18	123.9 (5)	F4A—C25A—C24A	120.5 (10)
C16—C17—C171	119.4 (4)	F4A—C25A—C26A	120.1 (10)
C18—C17—C171	116.6 (4)	C24A—C25A—C26A	119.4 (10)
N24—C18—C17	125.5 (5)	F5A—C26A—C21A	119.1 (10)
N24—C18—C19	105.6 (4)	F5A—C26A—C25A	118.1 (13)
C17—C18—C19	128.5 (5)	C21A—C26A—C25A	122.7 (10)
C18—C19—Br7	127.7 (4)	C122—C121—C12	120.3 (6)
C20—C19—Br7	123.0 (4)	C122—C121—C126	115.9 (6)
C20—C19—C18	108.8 (4)	C126—C121—C12	123.7 (6)
C1—C20—Br8	129.1 (4)	F11A—C122—C121	120.7 (8)
C19—C20—Br8	123.0 (4)	F11A—C122—C123	116.2 (8)
C19—C20—C1	107.5 (4)	C121—C122—C123	123.1 (8)
C22B—C21B—C2	129.4 (13)	F12A—C123—C122	121.7 (8)
C22B—C21B—C26B	116.1 (17)	F12A—C123—C124	120.4 (7)
C26B—C21B—C2	114.5 (12)	C124—C123—C122	117.9 (8)
F1B—C22B—C21B	116 (2)	F13A—C124—C123	119.6 (8)
F1B—C22B—C23B	121 (3)	F13A—C124—C125	118.9 (8)
C21B—C22B—C23B	123 (3)	C125—C124—C123	121.5 (7)
F2B—C23B—C22B	116 (2)	F14A—C125—C124	121.5 (7)
F2B—C23B—C24B	128 (2)	F14A—C125—C126	118.9 (8)
C24B—C23B—C22B	116 (2)	C124—C125—C126	119.6 (7)
F3B—C24B—C23B	112 (2)	F15A—C126—C121	117.8 (7)
C25B—C24B—F3B	125 (2)	F15A—C126—C125	120.1 (8)
C25B—C24B—C23B	123 (2)	C125—C126—C121	122.0 (8)
C24B—C25B—F4B	117 (2)

Br1—C4—C5—Br2	1.5 (7)	C12A—C12—C13—N23	−154.4 (5)
Br1—C4—C5—C6	177.4 (3)	C12A—C12—C13—C14	20.2 (8)
Br2—C5—C6—N21	171.6 (4)	C12A—C12F—C12E—F14B	−177 (3)
Br2—C5—C6—C7	−17.4 (8)	C12A—C12F—C12E—C12D	0.0
Br3—C9—C10—Br4	3.2 (6)	C12F—C12A—C12B—F11B	−180 (2)
Br3—C9—C10—C11	−170.2 (3)	C12F—C12A—C12B—C12C	0.0
Br4—C10—C11—N22	−172.6 (4)	C12F—C12E—C12D—F13B	173 (2)
Br4—C10—C11—C12	9.5 (8)	C12F—C12E—C12D—C12C	0.0
Br5—C14—C15—Br6	−6.7 (7)	C12E—C12D—C12C—F12B	179 (3)
Br5—C14—C15—C16	168.6 (4)	C12E—C12D—C12C—C12B	0.0
Br6—C15—C16—N23	172.5 (4)	C12D—C12C—C12B—F11B	180 (3)
Br6—C15—C16—C17	−9.6 (8)	C12D—C12C—C12B—C12A	0.0
Br7—C19—C20—Br8	1.0 (6)	C12B—C12A—C12F—F15B	−174 (3)
Br7—C19—C20—C1	−172.6 (4)	C12B—C12A—C12F—C12E	0.0
F1B—C22B—C23B—F2B	−2 (4)	C13—N23—C16—C15	4.3 (6)
F1B—C22B—C23B—C24B	−179 (3)	C13—N23—C16—C17	−173.7 (5)
F2B—C23B—C24B—F3B	3 (4)	C13—C12—C12A—C12F	−120.0 (10)
F2B—C23B—C24B—C25B	−179 (3)	C13—C12—C12A—C12B	61.6 (13)
F3B—C24B—C25B—F4B	0 (4)	C13—C12—C121—C122	56.6 (9)
F3B—C24B—C25B—C26B	−178 (3)	C13—C12—C121—C126	−122.9 (7)
F4B—C25B—C26B—F5B	1 (4)	C13—C14—C15—Br6	−175.7 (4)
F4B—C25B—C26B—C21B	180 (2)	C13—C14—C15—C16	−0.5 (6)
F6—C72—C73—F7	−0.8 (7)	C14—C15—C16—N23	−2.4 (6)
F6—C72—C73—C74	−179.6 (4)	C14—C15—C16—C17	175.6 (5)
F7—C73—C74—F8	−0.5 (7)	C15—C16—C17—C18	163.5 (5)
F7—C73—C74—C75	−179.8 (5)	C15—C16—C17—C171	−11.8 (8)
F8—C74—C75—F9	2.5 (8)	C16—N23—C13—C12	170.8 (5)
F8—C74—C75—C76	−177.2 (5)	C16—N23—C13—C14	−4.6 (6)
F9—C75—C76—F10	−0.8 (7)	C16—C17—C18—N24	−20.9 (8)
F9—C75—C76—C71	179.4 (5)	C16—C17—C18—C19	167.4 (5)
F12B—C12C—C12B—F11B	1 (2)	C16—C17—C171—C172	−64.6 (7)
F12B—C12C—C12B—C12A	−179 (2)	C16—C17—C171—C176	113.9 (6)
F13B—C12D—C12C—F12B	5 (3)	C17—C18—C19—Br7	−18.5 (8)
F13B—C12D—C12C—C12B	−173.8 (19)	C17—C18—C19—C20	169.5 (5)
F14B—C12E—C12D—F13B	−10 (3)	C17—C171—C172—F16	−0.3 (8)
F14B—C12E—C12D—C12C	177 (2)	C17—C171—C172—C173	178.8 (5)
F15B—C12F—C12E—F14B	−2 (2)	C17—C171—C176—F20	0.5 (8)
F15B—C12F—C12E—C12D	175 (2)	C17—C171—C176—C175	−178.8 (5)
F16—C172—C173—F17	−0.4 (8)	C18—N24—C1—C2	169.7 (5)
F16—C172—C173—C174	179.2 (5)	C18—N24—C1—C20	−6.1 (6)
F17—C173—C174—F18	0.4 (9)	C18—C17—C171—C172	119.7 (6)
F17—C173—C174—C175	179.1 (6)	C18—C17—C171—C176	−61.8 (7)
F18—C174—C175—F19	−0.4 (9)	C18—C19—C20—Br8	173.3 (4)
F18—C174—C175—C176	179.2 (5)	C18—C19—C20—C1	−0.2 (6)
F19—C175—C176—F20	0.1 (8)	C20—C1—C2—C3	−168.4 (5)
F19—C175—C176—C171	179.5 (5)	C20—C1—C2—C21B	8.4 (8)
N21—C3—C4—Br1	−173.3 (4)	C20—C1—C2—C21A	8.4 (8)
N21—C3—C4—C5	3.7 (6)	C21B—C2—C3—N21	−161.3 (5)
N21—C6—C7—C8	−19.1 (8)	C21B—C2—C3—C4	11.7 (8)
N21—C6—C7—C71	153.7 (5)	C21B—C22B—C23B—F2B	175 (3)
N22—C8—C9—Br3	168.2 (4)	C21B—C22B—C23B—C24B	−2 (4)
N22—C8—C9—C10	−3.2 (5)	C22B—C21B—C26B—F5B	178 (3)
N22—C11—C12—C12A	−157.2 (5)	C22B—C21B—C26B—C25B	−1 (4)
N22—C11—C12—C13	26.5 (8)	C22B—C23B—C24B—F3B	−180 (2)
N22—C11—C12—C121	−157.2 (5)	C22B—C23B—C24B—C25B	−2 (4)
N23—C13—C14—Br5	−165.5 (4)	C23B—C24B—C25B—F4B	−178 (2)
N23—C13—C14—C15	3.2 (6)	C23B—C24B—C25B—C26B	4 (4)
N23—C16—C17—C18	−18.8 (8)	C24B—C25B—C26B—F5B	178 (3)
N23—C16—C17—C171	165.9 (5)	C24B—C25B—C26B—C21B	−3 (4)
N24—C1—C2—C3	16.8 (8)	C26B—C21B—C22B—F1B	−180 (3)
N24—C1—C2—C21B	−166.5 (5)	C26B—C21B—C22B—C23B	3 (4)
N24—C1—C2—C21A	−166.5 (5)	C71—C7—C8—N22	162.3 (5)
N24—C1—C20—Br8	−169.3 (4)	C71—C7—C8—C9	−15.1 (8)
N24—C1—C20—C19	3.8 (6)	C71—C72—C73—F7	177.3 (5)
N24—C18—C19—Br7	168.5 (4)	C71—C72—C73—C74	−1.6 (8)
N24—C18—C19—C20	−3.4 (6)	C72—C71—C76—F10	178.7 (4)
C1—N24—C18—C17	−167.2 (5)	C72—C71—C76—C75	−1.5 (7)
C1—N24—C18—C19	6.0 (6)	C72—C73—C74—F8	178.4 (5)
C1—C2—C3—N21	15.3 (8)	C72—C73—C74—C75	−0.9 (8)
C1—C2—C3—C4	−171.6 (5)	C73—C74—C75—F9	−178.2 (5)
C1—C2—C21B—C22B	73 (2)	C73—C74—C75—C76	2.1 (8)
C1—C2—C21B—C26B	−107.6 (17)	C74—C75—C76—F10	178.9 (5)
C1—C2—C21A—C22A	69.4 (9)	C74—C75—C76—C71	−0.9 (8)
C1—C2—C21A—C26A	−108.8 (10)	C76—C71—C72—F6	−179.2 (4)
C2—C1—C20—Br8	15.1 (8)	C76—C71—C72—C73	2.8 (7)
C2—C1—C20—C19	−171.9 (5)	C171—C17—C18—N24	154.5 (5)
C2—C3—C4—Br1	12.9 (8)	C171—C17—C18—C19	−17.1 (8)
C2—C3—C4—C5	−170.1 (5)	C171—C172—C173—F17	−179.5 (5)
C2—C21B—C22B—F1B	0 (4)	C171—C172—C173—C174	0.1 (9)
C2—C21B—C22B—C23B	−177.5 (18)	C172—C171—C176—F20	179.1 (5)
C2—C21B—C26B—F5B	−1 (4)	C172—C171—C176—C175	−0.2 (8)
C2—C21B—C26B—C25B	180 (2)	C172—C173—C174—F18	−179.2 (5)
C2—C21A—C22A—F1A	2.4 (16)	C172—C173—C174—C175	−0.5 (9)
C2—C21A—C22A—C23A	−178.5 (9)	C173—C174—C175—F19	−179.1 (5)
C2—C21A—C26A—F5A	0.4 (17)	C173—C174—C175—C176	0.6 (10)
C2—C21A—C26A—C25A	177.9 (10)	C174—C175—C176—F20	−179.5 (5)
C3—N21—C6—C5	6.2 (5)	C174—C175—C176—C171	−0.2 (9)
C3—N21—C6—C7	−165.2 (5)	C176—C171—C172—F16	−178.8 (4)
C3—C2—C21B—C22B	−110 (2)	C176—C171—C172—C173	0.2 (8)
C3—C2—C21B—C26B	69.2 (17)	F1A—C22A—C23A—F2A	−0.3 (17)
C3—C2—C21A—C22A	−113.8 (9)	F1A—C22A—C23A—C24A	179.8 (10)
C3—C2—C21A—C26A	68.0 (11)	F2A—C23A—C24A—F3A	−0.3 (14)
C3—C4—C5—Br2	−175.6 (4)	F2A—C23A—C24A—C25A	179.5 (10)
C3—C4—C5—C6	0.2 (6)	F3A—C24A—C25A—F4A	−2.5 (15)
C4—C5—C6—N21	−4.0 (6)	F3A—C24A—C25A—C26A	180.0 (11)
C4—C5—C6—C7	167.1 (5)	F4A—C25A—C26A—F5A	0.3 (19)
C5—C6—C7—C8	170.9 (5)	F4A—C25A—C26A—C21A	−177.2 (11)
C5—C6—C7—C71	−16.2 (8)	F11A—C122—C123—F12A	−1.5 (12)
C6—N21—C3—C2	168.1 (5)	F11A—C122—C123—C124	178.6 (9)
C6—N21—C3—C4	−6.1 (6)	F12A—C123—C124—F13A	0.9 (12)
C6—C7—C8—N22	−24.6 (8)	F12A—C123—C124—C125	−177.8 (9)
C6—C7—C8—C9	157.9 (5)	F13A—C124—C125—F14A	−1.1 (13)
C6—C7—C71—C72	−62.6 (7)	F13A—C124—C125—C126	179.0 (8)
C6—C7—C71—C76	121.4 (5)	F14A—C125—C126—F15A	1.8 (12)
C7—C8—C9—Br3	−14.0 (8)	F14A—C125—C126—C121	−179.6 (9)
C7—C8—C9—C10	174.6 (5)	O25—C26—C27—C28	−32.3 (7)
C7—C71—C72—F6	4.6 (7)	C26—O25—C29—C28	3.1 (10)
C7—C71—C72—C73	−173.4 (5)	C26—C27—C28—C29	33.1 (8)
C7—C71—C76—F10	−5.2 (7)	C27—C28—C29—O25	−23.0 (10)
C7—C71—C76—C75	174.6 (5)	C29—O25—C26—C27	18.4 (8)
C8—N22—C11—C10	−2.7 (6)	C21A—C2—C3—N21	−161.3 (5)
C8—N22—C11—C12	175.5 (5)	C21A—C2—C3—C4	11.7 (8)
C8—C7—C71—C72	110.8 (5)	C21A—C22A—C23A—F2A	−179.5 (10)
C8—C7—C71—C76	−65.1 (6)	C21A—C22A—C23A—C24A	0.6 (17)
C8—C9—C10—Br4	175.0 (4)	C22A—C21A—C26A—F5A	−177.8 (12)
C8—C9—C10—C11	1.7 (6)	C22A—C21A—C26A—C25A	−0.3 (18)
C9—C10—C11—N22	0.5 (6)	C22A—C23A—C24A—F3A	179.6 (10)
C9—C10—C11—C12	−177.5 (5)	C22A—C23A—C24A—C25A	−0.6 (15)
C10—C11—C12—C12A	20.4 (8)	C23A—C24A—C25A—F4A	177.7 (10)
C10—C11—C12—C13	−155.8 (5)	C23A—C24A—C25A—C26A	0.2 (16)
C10—C11—C12—C121	20.4 (8)	C24A—C25A—C26A—F5A	177.8 (11)
C11—N22—C8—C7	−174.3 (5)	C24A—C25A—C26A—C21A	0.3 (19)
C11—N22—C8—C9	3.6 (5)	C26A—C21A—C22A—F1A	−179.3 (12)
C11—C12—C12A—C12F	63.7 (11)	C26A—C21A—C22A—C23A	−0.2 (17)
C11—C12—C12A—C12B	−114.7 (12)	C121—C12—C13—N23	−154.4 (5)
C11—C12—C13—N23	21.8 (8)	C121—C12—C13—C14	20.2 (8)
C11—C12—C13—C14	−163.6 (5)	C121—C122—C123—F12A	−180.0 (9)
C11—C12—C121—C122	−119.7 (7)	C121—C122—C123—C124	0.2 (11)
C11—C12—C121—C126	60.7 (9)	C122—C121—C126—F15A	−179.5 (9)
C12—C12A—C12F—F15B	8 (3)	C122—C121—C126—C125	1.8 (11)
C12—C12A—C12F—C12E	−178.5 (7)	C122—C123—C124—F13A	−179.3 (8)
C12—C12A—C12B—F11B	−2 (3)	C122—C123—C124—C125	2.0 (12)
C12—C12A—C12B—C12C	178.3 (8)	C123—C124—C125—F14A	177.6 (9)
C12—C13—C14—Br5	19.3 (8)	C123—C124—C125—C126	−2.3 (12)
C12—C13—C14—C15	−172.1 (5)	C124—C125—C126—F15A	−178.3 (9)
C12—C121—C122—F11A	0.0 (12)	C124—C125—C126—C121	0.3 (12)
C12—C121—C122—C123	178.3 (6)	C126—C121—C122—F11A	179.6 (9)
C12—C121—C126—F15A	0.0 (12)	C126—C121—C122—C123	−2.1 (11)
C12—C121—C126—C125	−178.6 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N22—H22···O25	0.97 (1)	1.92 (2)	2.849 (6)	158 (5)

Calculated mean distances, angles and structural parameters (Å, °) for compounds 1–6 top

Measured mean bond distances, angles, mean-plane angles, calculated NSD values, intramolecular contacts and mean-plane deviations for atom groups.

	Br₈TPFPP·CHCl₃	Br₈TPFPP1·THF	H₈TPFPP·dioxane	F₈TPFPP	Cl₈TPFPP	Br₈TPFPP·C₆H₄Cl₂	Br₈TPP·DMF
	1·CHCl₃	1·THF	2	3	4	1·C₆H₄Cl₂	6
	This work	This work	(HALZUP; Dogutan et al., 2010)	(GODYON; Leroy et al., 1999)	(ZALHUP; Birnbaum et al., 1995)	(ZALJEB; Birnbaum et al., 1995)	(RONROB; Spyroulias et al., 1997)
Bond lengths
N-C_a	1.368 (7)	1.366 (6)	1.358	1.370	1.372	1.367	1.362
C_a-C_b	1.440 (20)	1.450 (2)	1.450	1.438	1.448	1.457	1.435
C_a-C_m	1.406 (10)	1.408 (4)	1.395	1.399	1.402	1.406	1.415
C_b-C_b	1.361 (10)	1.357 (12)	1.345	1.332	1.347	1.349	1.348

Bond angles
N-C_a-C_m	123.1 (7)	123.7 (12)	126.1	126.6	125.4	124.5	123.1
N-C_a-C_b	110.0 (6)	110.0 (6)	108.8	107.5	107.2	108.1	107.5
C_a-N-C_a	109.0 (4)	109.0 (3)	108.1	108.7	109.5	108.7	109.4
C_a-C_m-C_a	123.0 (9)	123.8 (7)	125.8	125.4	125.7	123.4	120.9
C_a-C_b-C_b	107.4 (12)	107.5 (9)	107.1	108.1	108.0	107.4	107.7
C_m-C_a-C_b	129.0 (2)	128.3 (14)	125.0	125.9	127.2	127.1	129.3

Pyrrole mean-plane incline angles
<pyr_N21	27.8	25.6	0.7	3.1	14.6	25.6	39.1
<pyr_N22	26.9	29.5	0.4	3.4	15.7	20.4	39.1
<pyr_N23	36.9	36.5	0.7	3.1	14.9	25.6	39.1
<pyr_N24	32.1	22.3	0.4	3.4	14.0	20.4	39.1
Mean(<pyr)	30.0	28.5	0.6	3.2	14.8	23.0	39.1

Structural parameters
Δip^a	0.59 (11)	0.42 (10)	0.182 (12)	0.23 (2)	0.07 (4)	0.31 (7)	0.8 (2)
Δoop^b	3.46 (7)	3.17 (7)	0.01 (9)	0.246 (8)	1.91 (2)	2.73 (5)	3.790 (120)
N21···N22	2.866 (3)	2.43 (5)	2.927	2.921	2.943	2.923	2.958
N22···N23	2.931 (3)	2.32 (5)	2.895	2.942	2.939	2.86	2.958
N23···N24	2.895 (3)	2.61 (6)	2.927	2.921	2.942	2.923	2.958
N24···N21	2.928 (3)	2.60 (6)	2.895	2.942	2.925	2.86	2.958
Δ24^c	0.543	0.497	0.008	0.046	0.308	0.442	0.616
ΔN^d	0.075	0.090	0.018	0.046	0.088	0.077	0.034
ΔC_m^e	0.036	0.017	0.009	0.061	0.009	0.091	0.317
ΔC_a^f	0.418	0.379	0.007	0.029	0.250	0.339	0.409
ΔC_b^g	1.156	1.060	0.005	0.055	0.626	0.903	1.264

(a) Simulated total in-plane distortion; (b) simulated total out-of-plane distortion; (c) average deviation from the least-squares plane of the 24-macrocycle atoms; (d) simulated displacement of the four internal nitrogen atoms from the 24-atom mean plane; (e) average deviation of the meso-carbon atoms from the 24-atom mean plane; (f) Average deviation of the α-carbon atoms from the 24-atom mean plane; (g) Average deviation of the β-carbon atoms from the 24-atom mean plane.

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Crystal structures of 2,3,7,8,12,13,17,18-octa­bromo-5,10,15,20-tetra­kis­(penta­fluoro­phen­yl)porphyrin as the chloro­form monosolvate and tetra­hydro­furan monosolvate

Supporting information

Key indicators

checkCIF/PLATON results

Crystal structures of 2,3,7,8,12,13,17,18-octabromo-5,10,15,20-tetrakis(pentafluorophenyl)porphyrin as the chloroform monosolvate and tetrahydrofuran monosolvate