Tri­fluoro­methane­sulfonate salt of 5,10,15,20-tetra­kis­(1-benzyl­pyridin-1-ium-4-yl)-21H,23H-porphyrin and its Ca^II complex

The synthesis and crystallization of a tri­fluoro­methane­sulfonate salt of 5,10,15,20-tetra­kis­(1-benzyl­pyridin-1-ium-4-yl)-21H,23H-porphyrin, C₆₈H₅₄N₈⁴⁺·4CF₃O₃S·4H₂O, 1·OTf, are reported. The asymmetric unit contains half a porphyrin mol­ecule, two tri­fluoro­methane­sulfonate anions and two water mol­ecules of crystallization. The macrocycle of tetra­pyrrole moieties is planar and unexpectedly it has coordinated Ca^II ions in occupational disorder. This Ca^II ion has only 10% occupancy (C₇₂H_61.80Ca_0.10F₁₂N₈O₁₆S₄).

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in main residue
• R factor = 0.043
• wR factor = 0.126
• Data-to-parameter ratio = 8.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT077_ALERT_4_C Unitcell Contains Non-integer Number of Atoms ..     Please Check
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       8.45 Note
PLAT220_ALERT_2_C NonSolvent   Resd 1  C   Ueq(max)/Ueq(min) Range        3.2 Ratio
PLAT260_ALERT_2_C Large Average Ueq of Residue Including        S1      0.105 Check
PLAT260_ALERT_2_C Large Average Ueq of Residue Including        S2      0.108 Check
PLAT260_ALERT_2_C Large Average Ueq of Residue Including       S1A      0.111 Check
PLAT260_ALERT_2_C Large Average Ueq of Residue Including       S2A      0.104 Check

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         67 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         58 Report
PLAT068_ALERT_1_G Reported F000 Differs from Calcd (or Missing)...     Please Check
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records         19 Report
PLAT174_ALERT_4_G The CIF-Embedded .res File Contains FLAT Records          4 Report
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          8 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          1 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          3 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          3 Report
PLAT188_ALERT_3_G A Non-default SIMU Restraint Value has been used     0.0100 Report
PLAT188_ALERT_3_G A Non-default SIMU Restraint Value has been used     0.0100 Report
PLAT188_ALERT_3_G A Non-default SIMU Restraint Value has been used     0.0100 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for First Par     0.0050 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for First Par     0.0050 Report
PLAT190_ALERT_3_G A Non-default RIGU Restraint Value for First Par     0.0050 Report
PLAT191_ALERT_3_G A Non-default SADI Restraint Value has been used     0.0010 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd    1)        34% 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
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd    4)       100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd    5)       100% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd    1)     129.90 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd    2)       4.54 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd    3)       4.38 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd    4)       3.46 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd    5)       3.62 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  O4       ..C25      .       2.81 Ang.
                                                      x,y,z  =      1_555 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  O8       ..C13A     .       2.93 Ang.
                                              x,3/2-y,1/2+z  =      4_576 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  O6A      ..C25      .       3.01 Ang.
                                                      x,y,z  =      1_555 Check
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle(s) in CIF ...       6.50 Deg.
              CA1  -N2   -H2A     1_555   1_555   1_555 ......     #  102 Check
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle(s) in CIF ...      31.17 Deg.
              N1   -C1   -CA1     1_555   1_555   1_555 ......     #  109 Check
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle(s) in CIF ...      32.48 Deg.
              N1   -C4   -CA1     1_555   1_555   1_555 ......     #  121 Check
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle(s) in CIF ...      34.39 Deg.
              N2   -C6   -CA1     1_555   1_555   1_555 ......     #  132 Check
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle(s) in CIF ...      33.08 Deg.
              N2   -C9   -CA1     1_555   1_555   1_555 ......     #  144 Check
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............       1623 Note
PLAT969_ALERT_5_G The 'Henn et al.' R-Factor-gap value ...........       4.96 Note
              Predicted wR2: Based on SigI   2  2.54 or SHELX Weight 12.95       
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         12 Info
PLAT992_ALERT_5_G Repd & Actual _reflns_number_gt Values Differ by          2 Check

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  11 ALERT type 2 Indicator that the structure model may be wrong or deficient
  10 ALERT type 3 Indicator that the structure quality may be low
  22 ALERT type 4 Improvement, methodology, query or suggestion
   3 ALERT type 5 Informative message, check

---

Computing details

(5,10,15,20-tetrakis(1-benzylpyridin-1-ium-4-yl)-21H,23H-porphyrin)calcium(II) tetrakis(trifluoromethanesulfonate) tetrahydrate

Crystal data

[Ca0.10(C68H53.81N8)](CF3O3S)4·4H2O	F(000) = 1703
Mr = 1655.20	Dx = 1.507 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 10.4506 (4) Å	Cell parameters from 9998 reflections
b = 15.6166 (6) Å	θ = 3.5–69.4°
c = 22.3537 (9) Å	µ = 2.18 mm^−1
β = 90.417 (2)°	T = 293 K
V = 3648.1 (2) Å^3	Plate, red
Z = 2	0.49 × 0.28 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer	6684 independent reflections
Radiation source: Incoatec ImuS	5995 reflections with I > 2σ(I)
Mirrors monochromator	Rint = 0.035
ω scans	θmax = 68.2°, θmin = 3.5°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −12→12
Tmin = 0.586, Tmax = 0.753	k = −18→18
50051 measured reflections	l = −26→26

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: mixed
wR(F^2) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0713P)^2 + 1.1304P] where P = (Fo^2 + 2Fc^2)/3
6684 reflections	(Δ/σ)max = 0.001
791 parameters	Δρmax = 0.22 e Å^−3
1623 restraints	Δρmin = −0.27 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)
Ca1	0.500000	1.000000	0.500000	0.0372 (17)	0.096 (2)
O7	0.80659 (19)	0.66609 (16)	0.72189 (10)	0.1002 (6)
H7A	0.833 (3)	0.7028 (17)	0.6959 (12)	0.120*
H7B	0.767 (3)	0.6257 (16)	0.7019 (14)	0.120*
O8	1.04027 (18)	0.63868 (14)	0.78449 (9)	0.0916 (5)
H8A	1.050 (3)	0.5840 (12)	0.7886 (15)	0.110*
H8B	0.970 (2)	0.6459 (18)	0.7624 (13)	0.110*
N1	0.59926 (11)	0.99267 (7)	0.42253 (5)	0.0354 (3)
N2	0.56666 (12)	0.87932 (8)	0.52642 (6)	0.0368 (3)
H2A	0.546 (2)	0.9301 (11)	0.5186 (10)	0.055*	0.904 (2)
N4	0.39344 (13)	0.69299 (8)	0.76441 (6)	0.0429 (3)
C1	0.60390 (13)	1.05069 (9)	0.37688 (6)	0.0356 (3)
C2	0.67922 (15)	1.01782 (10)	0.32765 (7)	0.0422 (3)
H2	0.694744	1.045030	0.291413	0.051*
C3	0.72193 (15)	0.94075 (10)	0.34459 (7)	0.0411 (3)
H3	0.773680	0.904196	0.322554	0.049*
C4	0.67194 (13)	0.92520 (9)	0.40395 (6)	0.0349 (3)
C5	0.69278 (13)	0.84937 (9)	0.43609 (7)	0.0360 (3)
C6	0.64139 (13)	0.82779 (9)	0.49145 (7)	0.0368 (3)
C7	0.65604 (16)	0.74870 (10)	0.52261 (7)	0.0447 (4)
H7	0.702550	0.701645	0.509449	0.054*
C8	0.59099 (16)	0.75367 (10)	0.57446 (7)	0.0445 (4)
H8	0.584306	0.710646	0.603031	0.053*
C9	0.53414 (14)	0.83692 (9)	0.57764 (7)	0.0375 (3)
C10	0.45622 (14)	0.86894 (9)	0.62318 (6)	0.0371 (3)
C11	0.7804 (8)	0.7846 (4)	0.4085 (3)	0.0374 (12)	0.612 (10)
C12	0.9104 (9)	0.7940 (6)	0.4176 (3)	0.0481 (13)	0.612 (10)
H12	0.940570	0.838965	0.441047	0.058*	0.612 (10)
C13	0.9959 (8)	0.7378 (5)	0.3925 (3)	0.0504 (12)	0.612 (10)
H13	1.083126	0.745656	0.398884	0.060*	0.612 (10)
N3	0.9558 (7)	0.6728 (5)	0.3594 (3)	0.0508 (12)	0.612 (10)
C14	0.8305 (7)	0.6615 (5)	0.3485 (3)	0.0561 (14)	0.612 (10)
H14	0.803491	0.616189	0.324510	0.067*	0.612 (10)
C15	0.7418 (8)	0.7163 (6)	0.3726 (3)	0.0503 (14)	0.612 (10)
H15	0.655216	0.707711	0.364834	0.060*	0.612 (10)
C16	1.0498 (6)	0.6067 (4)	0.3377 (3)	0.0619 (12)	0.612 (10)
H16A	1.135832	0.629905	0.339932	0.074*	0.612 (10)
H16B	1.031262	0.592725	0.296310	0.074*	0.612 (10)
C17	1.0419 (4)	0.5266 (4)	0.3755 (3)	0.0632 (11)	0.612 (10)
C18	1.1090 (6)	0.5187 (4)	0.4289 (3)	0.0873 (15)	0.612 (10)
H18	1.160537	0.563880	0.441504	0.105*	0.612 (10)
C19	1.1021 (7)	0.4457 (4)	0.4644 (3)	0.1036 (17)	0.612 (10)
H19	1.147129	0.441612	0.500332	0.124*	0.612 (10)
C20	1.0256 (7)	0.3795 (5)	0.4440 (4)	0.1120 (17)	0.612 (10)
H20	1.018701	0.329820	0.466664	0.134*	0.612 (10)
C21	0.9596 (8)	0.3860 (5)	0.3909 (4)	0.1020 (17)	0.612 (10)
H21	0.910071	0.340266	0.377636	0.122*	0.612 (10)
C22	0.9659 (7)	0.4591 (5)	0.3571 (3)	0.0855 (16)	0.612 (10)
H22	0.918870	0.463208	0.321773	0.103*	0.612 (10)
C11A	0.7828 (12)	0.7861 (7)	0.4086 (6)	0.040 (2)	0.388 (10)
C12A	0.9133 (13)	0.7979 (9)	0.4049 (5)	0.0452 (17)	0.388 (10)
H12A	0.951268	0.847263	0.420082	0.054*	0.388 (10)
C13A	0.9868 (12)	0.7350 (8)	0.3780 (5)	0.0528 (19)	0.388 (10)
H13A	1.074842	0.742423	0.375102	0.063*	0.388 (10)
N3A	0.9330 (11)	0.6644 (7)	0.3563 (5)	0.0518 (17)	0.388 (10)
C14A	0.8065 (11)	0.6528 (8)	0.3594 (5)	0.0552 (18)	0.388 (10)
H14A	0.770732	0.603188	0.343482	0.066*	0.388 (10)
C15A	0.7288 (13)	0.7118 (9)	0.3855 (5)	0.0465 (17)	0.388 (10)
H15A	0.641053	0.702516	0.387672	0.056*	0.388 (10)
C16A	1.0104 (10)	0.5950 (7)	0.3270 (4)	0.0682 (19)	0.388 (10)
H16C	0.967560	0.576423	0.290598	0.082*	0.388 (10)
H16D	1.093687	0.617482	0.316204	0.082*	0.388 (10)
C17A	1.0272 (8)	0.5203 (7)	0.3681 (4)	0.0686 (18)	0.388 (10)
C18A	1.1372 (8)	0.5140 (5)	0.4025 (5)	0.0820 (18)	0.388 (10)
H18A	1.201016	0.555439	0.400538	0.098*	0.388 (10)
C19A	1.1489 (10)	0.4442 (6)	0.4397 (5)	0.101 (2)	0.388 (10)
H19A	1.222437	0.438679	0.463098	0.122*	0.388 (10)
C20A	1.0556 (11)	0.3822 (8)	0.4435 (5)	0.108 (2)	0.388 (10)
H20A	1.066684	0.335977	0.469277	0.129*	0.388 (10)
C21A	0.9457 (12)	0.3886 (8)	0.4092 (6)	0.101 (2)	0.388 (10)
H21A	0.881987	0.347167	0.411648	0.121*	0.388 (10)
C22A	0.9325 (10)	0.4580 (7)	0.3711 (5)	0.083 (2)	0.388 (10)
H22A	0.859548	0.462926	0.347272	0.099*	0.388 (10)
C23	0.43381 (14)	0.81063 (9)	0.67489 (7)	0.0381 (3)
C24	0.53387 (15)	0.78163 (11)	0.71026 (7)	0.0440 (4)
H24	0.616172	0.802527	0.704421	0.053*
C25	0.51145 (16)	0.72196 (11)	0.75399 (7)	0.0467 (4)
H25	0.579579	0.701332	0.776780	0.056*
C26	0.29349 (16)	0.72276 (11)	0.73289 (8)	0.0495 (4)
H26	0.211397	0.703608	0.741500	0.059*
C27	0.31134 (15)	0.78131 (11)	0.68799 (8)	0.0474 (4)
H27	0.241424	0.801500	0.666221	0.057*
C28	0.37257 (19)	0.62615 (11)	0.81052 (8)	0.0508 (4)
H28A	0.449629	0.591909	0.814403	0.061*
H28B	0.304103	0.588619	0.797218	0.061*
C29	0.33906 (15)	0.66198 (11)	0.87083 (7)	0.0434 (4)
C30	0.28792 (19)	0.60547 (13)	0.91228 (8)	0.0565 (4)
H30	0.273460	0.548720	0.901588	0.068*
C31	0.2586 (2)	0.63286 (17)	0.96894 (9)	0.0712 (6)
H31	0.223618	0.594628	0.996221	0.085*
C32	0.2804 (2)	0.71607 (18)	0.98559 (9)	0.0730 (6)
H32	0.260240	0.734238	1.024009	0.088*
C33	0.3319 (2)	0.77247 (15)	0.94539 (10)	0.0674 (5)
H33	0.347823	0.828791	0.956728	0.081*
C34	0.36049 (17)	0.74569 (12)	0.88786 (9)	0.0536 (4)
H34	0.394279	0.784401	0.860588	0.064*
C35	0.9697 (7)	0.9025 (5)	0.5890 (3)	0.0690 (15)	0.567 (4)
F1	1.0514 (5)	0.9648 (4)	0.58440 (18)	0.1336 (18)	0.567 (4)
F2	1.0197 (6)	0.8344 (3)	0.5647 (2)	0.1305 (17)	0.567 (4)
F3	0.8743 (4)	0.9241 (3)	0.55352 (13)	0.1006 (10)	0.567 (4)
S1	0.9191 (2)	0.8838 (2)	0.66580 (13)	0.0600 (6)	0.567 (4)
O1	0.8216 (4)	0.8207 (3)	0.6574 (2)	0.1173 (15)	0.567 (4)
O2	0.8799 (6)	0.9651 (3)	0.6854 (2)	0.1189 (16)	0.567 (4)
O3	1.0294 (4)	0.8502 (4)	0.69258 (18)	0.1132 (15)	0.567 (4)
C35A	0.9759 (10)	0.9014 (7)	0.5917 (4)	0.075 (2)	0.433 (4)
F1A	1.0989 (3)	0.8891 (4)	0.59294 (18)	0.1000 (14)	0.433 (4)
F2A	0.9287 (7)	0.8438 (5)	0.5565 (2)	0.141 (2)	0.433 (4)
F3A	0.9587 (7)	0.9759 (4)	0.5681 (3)	0.134 (2)	0.433 (4)
S1A	0.9040 (4)	0.8957 (3)	0.6639 (2)	0.0908 (13)	0.433 (4)
O1A	0.7752 (4)	0.9047 (4)	0.6556 (2)	0.1127 (18)	0.433 (4)
O2A	0.9687 (7)	0.9624 (4)	0.6962 (3)	0.114 (2)	0.433 (4)
O3A	0.9478 (8)	0.8153 (4)	0.6862 (3)	0.124 (2)	0.433 (4)
C36	0.4698 (8)	0.5056 (5)	0.5924 (4)	0.0843 (17)	0.547 (12)
F4	0.4050 (9)	0.5732 (5)	0.5755 (4)	0.1231 (19)	0.547 (12)
F5	0.5709 (6)	0.5059 (6)	0.5597 (3)	0.121 (2)	0.547 (12)
F6	0.4130 (10)	0.4395 (4)	0.5706 (3)	0.121 (2)	0.547 (12)
S2	0.5069 (7)	0.4987 (3)	0.6715 (2)	0.0864 (13)	0.547 (12)
O4	0.5684 (12)	0.5790 (6)	0.6824 (6)	0.091 (2)	0.547 (12)
O5	0.5905 (11)	0.4265 (4)	0.6737 (3)	0.115 (2)	0.547 (12)
O6	0.3877 (9)	0.4856 (7)	0.6996 (4)	0.125 (3)	0.547 (12)
C36A	0.4403 (12)	0.5242 (7)	0.5903 (4)	0.090 (2)	0.453 (12)
F4A	0.3819 (10)	0.6009 (6)	0.5898 (5)	0.126 (3)	0.453 (12)
F5A	0.5411 (11)	0.5416 (6)	0.5586 (4)	0.124 (3)	0.453 (12)
F6A	0.3557 (10)	0.4696 (7)	0.5688 (4)	0.122 (3)	0.453 (12)
S2A	0.4801 (7)	0.5013 (3)	0.6668 (3)	0.0694 (9)	0.453 (12)
O4A	0.5144 (11)	0.4154 (4)	0.6694 (4)	0.114 (2)	0.453 (12)
O5A	0.3550 (8)	0.5159 (6)	0.6925 (4)	0.091 (2)	0.453 (12)
O6A	0.5726 (14)	0.5616 (9)	0.6850 (8)	0.098 (3)	0.453 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ca1	0.044 (3)	0.030 (2)	0.037 (3)	0.0098 (16)	0.0126 (17)	0.0093 (17)
O7	0.0761 (11)	0.1164 (17)	0.1084 (15)	0.0033 (10)	0.0128 (10)	0.0417 (13)
O8	0.0759 (11)	0.1117 (14)	0.0873 (12)	−0.0215 (11)	0.0056 (9)	0.0076 (12)
N1	0.0385 (6)	0.0301 (6)	0.0376 (6)	0.0035 (5)	0.0065 (5)	0.0050 (5)
N2	0.0401 (6)	0.0306 (6)	0.0399 (6)	0.0069 (5)	0.0082 (5)	0.0080 (5)
N4	0.0508 (7)	0.0382 (7)	0.0399 (7)	0.0066 (5)	0.0117 (6)	0.0104 (5)
C1	0.0364 (7)	0.0339 (7)	0.0366 (7)	0.0006 (5)	0.0052 (6)	0.0055 (6)
C2	0.0504 (8)	0.0398 (8)	0.0365 (8)	0.0024 (6)	0.0100 (6)	0.0056 (6)
C3	0.0458 (8)	0.0377 (8)	0.0401 (8)	0.0044 (6)	0.0118 (6)	0.0007 (6)
C4	0.0349 (7)	0.0326 (7)	0.0373 (7)	0.0012 (5)	0.0053 (5)	0.0020 (6)
C5	0.0356 (7)	0.0317 (7)	0.0408 (8)	0.0030 (6)	0.0043 (6)	0.0011 (6)
C6	0.0371 (7)	0.0326 (7)	0.0407 (8)	0.0048 (5)	0.0048 (6)	0.0041 (6)
C7	0.0521 (9)	0.0337 (7)	0.0484 (9)	0.0130 (6)	0.0090 (7)	0.0060 (7)
C8	0.0545 (9)	0.0334 (7)	0.0456 (8)	0.0086 (6)	0.0080 (7)	0.0113 (6)
C9	0.0397 (7)	0.0336 (7)	0.0394 (8)	0.0034 (6)	0.0052 (6)	0.0080 (6)
C10	0.0386 (7)	0.0346 (7)	0.0381 (7)	0.0018 (6)	0.0045 (6)	0.0081 (6)
C11	0.042 (2)	0.032 (2)	0.038 (2)	0.007 (2)	0.007 (2)	0.009 (2)
C12	0.0457 (19)	0.054 (2)	0.044 (3)	0.0071 (17)	0.007 (2)	−0.007 (2)
C13	0.0452 (18)	0.062 (2)	0.044 (3)	0.0094 (15)	0.0027 (18)	−0.004 (2)
N3	0.050 (2)	0.046 (2)	0.0563 (19)	0.0123 (17)	0.0144 (16)	0.0042 (16)
C14	0.066 (3)	0.041 (2)	0.061 (3)	0.000 (2)	0.022 (2)	−0.013 (2)
C15	0.047 (2)	0.047 (2)	0.058 (3)	−0.0005 (17)	0.008 (2)	−0.009 (2)
C16	0.057 (2)	0.061 (2)	0.068 (2)	0.0204 (19)	0.0158 (19)	−0.0117 (18)
C17	0.062 (2)	0.048 (2)	0.080 (2)	0.0226 (18)	0.0039 (19)	−0.0120 (18)
C18	0.086 (3)	0.070 (2)	0.105 (3)	0.005 (2)	−0.022 (3)	0.006 (3)
C19	0.107 (4)	0.085 (3)	0.118 (4)	0.021 (3)	−0.030 (3)	0.019 (3)
C20	0.115 (4)	0.068 (3)	0.153 (4)	0.013 (3)	−0.020 (3)	0.025 (3)
C21	0.115 (3)	0.063 (2)	0.128 (4)	−0.002 (2)	−0.014 (3)	−0.012 (3)
C22	0.098 (4)	0.068 (2)	0.090 (3)	0.011 (3)	−0.007 (3)	−0.019 (2)
C11A	0.045 (3)	0.036 (4)	0.040 (4)	0.007 (3)	0.007 (4)	0.003 (3)
C12A	0.042 (3)	0.048 (3)	0.046 (4)	0.002 (2)	0.010 (3)	0.003 (3)
C13A	0.049 (3)	0.063 (3)	0.047 (4)	0.016 (3)	0.014 (3)	0.005 (3)
N3A	0.056 (3)	0.045 (3)	0.055 (3)	0.015 (3)	0.024 (3)	0.005 (2)
C14A	0.062 (3)	0.041 (3)	0.063 (4)	0.001 (3)	0.027 (3)	0.001 (3)
C15A	0.050 (3)	0.038 (3)	0.051 (4)	0.005 (2)	0.021 (3)	−0.003 (3)
C16A	0.070 (4)	0.065 (3)	0.070 (3)	0.024 (3)	0.018 (3)	−0.005 (3)
C17A	0.073 (3)	0.052 (3)	0.081 (3)	0.022 (3)	0.001 (3)	−0.014 (3)
C18A	0.076 (3)	0.058 (3)	0.112 (4)	0.018 (3)	−0.010 (3)	0.009 (3)
C19A	0.090 (4)	0.073 (3)	0.141 (5)	0.021 (3)	−0.027 (4)	0.025 (4)
C20A	0.102 (4)	0.067 (4)	0.154 (4)	0.017 (3)	−0.024 (4)	0.026 (4)
C21A	0.106 (4)	0.068 (3)	0.129 (5)	0.004 (3)	−0.013 (4)	0.011 (4)
C22A	0.082 (4)	0.067 (3)	0.099 (4)	0.014 (3)	−0.005 (3)	−0.005 (3)
C23	0.0429 (8)	0.0335 (7)	0.0379 (7)	0.0049 (6)	0.0083 (6)	0.0054 (6)
C24	0.0396 (8)	0.0484 (9)	0.0440 (8)	0.0024 (6)	0.0072 (6)	0.0107 (7)
C25	0.0457 (8)	0.0521 (9)	0.0424 (8)	0.0100 (7)	0.0046 (6)	0.0121 (7)
C26	0.0425 (8)	0.0504 (9)	0.0558 (10)	−0.0014 (7)	0.0105 (7)	0.0133 (8)
C27	0.0404 (8)	0.0492 (9)	0.0526 (9)	0.0041 (7)	0.0028 (7)	0.0153 (7)
C28	0.0670 (11)	0.0384 (8)	0.0472 (9)	0.0053 (7)	0.0139 (8)	0.0137 (7)
C29	0.0401 (8)	0.0475 (9)	0.0428 (8)	0.0024 (6)	0.0042 (6)	0.0106 (7)
C30	0.0639 (11)	0.0555 (10)	0.0503 (10)	−0.0009 (8)	0.0088 (8)	0.0174 (8)
C31	0.0764 (13)	0.0886 (16)	0.0488 (11)	0.0090 (12)	0.0159 (9)	0.0250 (11)
C32	0.0722 (13)	0.1041 (18)	0.0428 (10)	0.0168 (12)	0.0035 (9)	−0.0010 (11)
C33	0.0629 (12)	0.0715 (13)	0.0677 (13)	0.0035 (10)	−0.0010 (10)	−0.0145 (11)
C34	0.0506 (9)	0.0519 (10)	0.0584 (10)	−0.0035 (7)	0.0103 (8)	0.0039 (8)
C35	0.064 (3)	0.077 (3)	0.066 (3)	−0.005 (3)	0.014 (2)	−0.009 (3)
F1	0.136 (3)	0.155 (4)	0.109 (3)	−0.087 (3)	0.011 (3)	0.012 (3)
F2	0.158 (4)	0.116 (3)	0.118 (3)	0.044 (3)	0.059 (3)	−0.018 (2)
F3	0.116 (2)	0.119 (3)	0.0660 (15)	0.000 (2)	−0.0130 (15)	−0.0059 (16)
S1	0.0418 (6)	0.0827 (13)	0.0557 (10)	0.0037 (7)	0.0140 (5)	0.0009 (8)
O1	0.094 (3)	0.140 (4)	0.118 (3)	−0.049 (3)	0.016 (2)	0.024 (3)
O2	0.151 (4)	0.108 (3)	0.098 (3)	0.044 (3)	0.017 (3)	−0.036 (2)
O3	0.079 (2)	0.174 (4)	0.086 (2)	0.033 (3)	−0.0029 (19)	0.013 (3)
C35A	0.070 (3)	0.084 (4)	0.070 (4)	−0.002 (3)	−0.004 (3)	−0.003 (3)
F1A	0.0652 (19)	0.153 (4)	0.082 (2)	0.019 (2)	0.0136 (16)	−0.003 (3)
F2A	0.137 (4)	0.190 (5)	0.096 (3)	−0.030 (4)	−0.010 (3)	−0.069 (3)
F3A	0.141 (5)	0.136 (4)	0.126 (4)	0.039 (4)	0.049 (4)	0.069 (3)
S1A	0.109 (3)	0.087 (2)	0.0757 (17)	−0.0344 (18)	−0.0129 (16)	0.0161 (14)
O1A	0.073 (3)	0.150 (5)	0.116 (4)	−0.024 (3)	0.033 (2)	0.007 (3)
O2A	0.128 (4)	0.126 (4)	0.088 (3)	−0.041 (4)	0.019 (3)	−0.029 (3)
O3A	0.162 (6)	0.093 (3)	0.117 (4)	−0.014 (4)	−0.003 (4)	0.048 (3)
C36	0.110 (4)	0.067 (3)	0.076 (3)	−0.003 (3)	0.001 (3)	0.004 (2)
F4	0.160 (4)	0.092 (4)	0.117 (4)	0.034 (3)	−0.041 (3)	−0.009 (3)
F5	0.124 (3)	0.169 (6)	0.071 (2)	0.025 (3)	0.0232 (19)	0.011 (4)
F6	0.194 (6)	0.093 (3)	0.075 (2)	−0.041 (3)	−0.013 (4)	−0.009 (2)
S2	0.137 (3)	0.0700 (16)	0.0527 (11)	0.0024 (14)	0.0088 (16)	−0.0095 (9)
O4	0.129 (4)	0.053 (3)	0.091 (3)	0.010 (2)	−0.003 (3)	−0.010 (2)
O5	0.191 (6)	0.062 (2)	0.091 (3)	0.031 (3)	−0.018 (4)	−0.010 (2)
O6	0.142 (5)	0.155 (6)	0.080 (3)	−0.033 (4)	0.026 (4)	0.007 (4)
C36A	0.131 (4)	0.072 (4)	0.068 (3)	−0.026 (4)	−0.007 (3)	0.017 (3)
F4A	0.136 (5)	0.099 (5)	0.144 (6)	−0.015 (4)	−0.027 (4)	0.026 (4)
F5A	0.169 (6)	0.117 (5)	0.085 (3)	−0.039 (4)	0.036 (4)	−0.001 (4)
F6A	0.156 (6)	0.132 (5)	0.078 (3)	−0.060 (4)	−0.017 (4)	−0.001 (4)
S2A	0.1048 (19)	0.0401 (12)	0.0632 (16)	−0.0050 (10)	−0.0020 (11)	−0.0086 (9)
O4A	0.162 (6)	0.056 (3)	0.125 (4)	0.018 (4)	−0.023 (5)	−0.012 (2)
O5A	0.111 (4)	0.094 (4)	0.069 (3)	0.005 (3)	0.010 (3)	−0.021 (3)
O6A	0.111 (5)	0.071 (6)	0.111 (5)	−0.008 (4)	−0.037 (4)	−0.019 (5)

Geometric parameters (Å, º)

Ca1—N1^i	2.0283 (12)	C13A—N3A	1.329 (11)
Ca1—N1	2.0284 (12)	C13A—H13A	0.9300
Ca1—N2^i	2.0927 (12)	N3A—C14A	1.337 (10)
Ca1—N2	2.0928 (12)	N3A—C16A	1.505 (10)
Ca1—C4	3.0430 (14)	C14A—C15A	1.362 (11)
Ca1—C4^i	3.0430 (14)	C14A—H14A	0.9300
Ca1—C1	3.0698 (14)	C15A—H15A	0.9300
Ca1—C1^i	3.0698 (14)	C16A—C17A	1.495 (10)
Ca1—C6	3.0751 (14)	C16A—H16C	0.9700
Ca1—C6^i	3.0751 (14)	C16A—H16D	0.9700
Ca1—C9^i	3.1010 (14)	C17A—C18A	1.382 (7)
Ca1—C9	3.1011 (14)	C17A—C22A	1.390 (7)
Ca1—H2A	1.263 (17)	C18A—C19A	1.377 (7)
Ca1—H2A^i	1.263 (17)	C18A—H18A	0.9300
O7—H7A	0.862 (18)	C19A—C20A	1.377 (8)
O7—H7B	0.875 (17)	C19A—H19A	0.9300
O8—H8A	0.865 (17)	C20A—C21A	1.380 (8)
O8—H8B	0.885 (17)	C20A—H20A	0.9300
N1—C4	1.3653 (18)	C21A—C22A	1.385 (7)
N1—C1	1.3658 (18)	C21A—H21A	0.9300
N2—C9	1.3677 (19)	C22A—H22A	0.9300
N2—C6	1.3702 (19)	C23—C24	1.383 (2)
N2—H2A	0.839 (16)	C23—C27	1.392 (2)
N4—C25	1.336 (2)	C24—C25	1.372 (2)
N4—C26	1.339 (2)	C24—H24	0.9300
N4—C28	1.4843 (19)	C25—H25	0.9300
C1—C10^i	1.404 (2)	C26—C27	1.371 (2)
C1—C2	1.451 (2)	C26—H26	0.9300
C2—C3	1.337 (2)	C27—H27	0.9300
C2—H2	0.9300	C28—C29	1.503 (2)
C3—C4	1.450 (2)	C28—H28A	0.9700
C3—H3	0.9300	C28—H28B	0.9700
C4—C5	1.401 (2)	C29—C34	1.379 (3)
C5—C6	1.394 (2)	C29—C30	1.389 (2)
C5—C11A	1.499 (2)	C30—C31	1.374 (3)
C5—C11	1.500 (2)	C30—H30	0.9300
C6—C7	1.426 (2)	C31—C32	1.370 (4)
C7—C8	1.350 (2)	C31—H31	0.9300
C7—H7	0.9300	C32—C33	1.372 (3)
C8—C9	1.431 (2)	C32—H32	0.9300
C8—H8	0.9300	C33—C34	1.387 (3)
C9—C10	1.401 (2)	C33—H33	0.9300
C10—C23	1.491 (2)	C34—H34	0.9300
C11—C12	1.380 (7)	C35—F1	1.298 (8)
C11—C15	1.393 (7)	C35—F2	1.305 (8)
C12—C13	1.375 (7)	C35—F3	1.314 (8)
C12—H12	0.9300	C35—S1	1.823 (7)
C13—N3	1.323 (7)	S1—O3	1.396 (4)
C13—H13	0.9300	S1—O2	1.405 (5)
N3—C14	1.342 (7)	S1—O1	1.429 (5)
N3—C16	1.506 (6)	C35A—F3A	1.289 (10)
C14—C15	1.375 (7)	C35A—F2A	1.292 (11)
C14—H14	0.9300	C35A—F1A	1.299 (11)
C15—H15	0.9300	C35A—S1A	1.786 (10)
C16—C17	1.513 (7)	S1A—O1A	1.365 (6)
C16—H16A	0.9700	S1A—O3A	1.425 (7)
C16—H16B	0.9700	S1A—O2A	1.434 (7)
C17—C22	1.381 (6)	C36—F6	1.285 (8)
C17—C18	1.385 (6)	C36—F5	1.288 (8)
C18—C19	1.391 (6)	C36—F4	1.309 (8)
C18—H18	0.9300	C36—S2	1.812 (8)
C19—C20	1.382 (6)	S2—O6	1.414 (8)
C19—H19	0.9300	S2—O5	1.426 (7)
C20—C21	1.373 (6)	S2—O4	1.430 (8)
C20—H20	0.9300	C36A—F5A	1.302 (10)
C21—C22	1.369 (6)	C36A—F6A	1.318 (9)
C21—H21	0.9300	C36A—F4A	1.345 (10)
C22—H22	0.9300	C36A—S2A	1.793 (9)
C11A—C12A	1.379 (11)	S2A—O4A	1.389 (8)
C11A—C15A	1.388 (12)	S2A—O6A	1.408 (9)
C12A—C13A	1.387 (11)	S2A—O5A	1.449 (8)
C12A—H12A	0.9300
N1^i—Ca1—N1	180.0	C14—N3—C16	119.3 (6)
N1^i—Ca1—N2^i	91.08 (5)	N3—C14—C15	120.5 (6)
N1—Ca1—N2^i	88.92 (5)	N3—C14—H14	119.8
N1^i—Ca1—N2	88.92 (5)	C15—C14—H14	119.8
N1—Ca1—N2	91.08 (5)	C14—C15—C11	120.7 (6)
N2^i—Ca1—N2	180.00 (7)	C14—C15—H15	119.7
N1^i—Ca1—C4	158.81 (4)	C11—C15—H15	119.7
N1—Ca1—C4	21.19 (4)	N3—C16—C17	110.4 (4)
N2^i—Ca1—C4	110.10 (4)	N3—C16—H16A	109.6
N2—Ca1—C4	69.90 (4)	C17—C16—H16A	109.6
N1^i—Ca1—C4^i	21.19 (4)	N3—C16—H16B	109.6
N1—Ca1—C4^i	158.81 (4)	C17—C16—H16B	109.6
N2^i—Ca1—C4^i	69.90 (4)	H16A—C16—H16B	108.1
N2—Ca1—C4^i	110.10 (4)	C22—C17—C18	118.4 (6)
C4—Ca1—C4^i	180.0	C22—C17—C16	120.0 (5)
N1^i—Ca1—C1	159.60 (4)	C18—C17—C16	121.7 (5)
N1—Ca1—C1	20.40 (4)	C17—C18—C19	122.4 (5)
N2^i—Ca1—C1	68.53 (4)	C17—C18—H18	118.8
N2—Ca1—C1	111.47 (4)	C19—C18—H18	118.8
C4—Ca1—C1	41.57 (4)	C20—C19—C18	117.2 (6)
C4^i—Ca1—C1	138.43 (4)	C20—C19—H19	121.4
N1^i—Ca1—C1^i	20.40 (4)	C18—C19—H19	121.4
N1—Ca1—C1^i	159.60 (4)	C21—C20—C19	121.0 (8)
N2^i—Ca1—C1^i	111.47 (4)	C21—C20—H20	119.5
N2—Ca1—C1^i	68.53 (4)	C19—C20—H20	119.5
C4—Ca1—C1^i	138.43 (4)	C22—C21—C20	120.8 (7)
C4^i—Ca1—C1^i	41.57 (4)	C22—C21—H21	119.6
C1—Ca1—C1^i	180.0	C20—C21—H21	119.6
N1^i—Ca1—C6	110.57 (4)	C21—C22—C17	120.1 (6)
N1—Ca1—C6	69.43 (4)	C21—C22—H22	119.9
N2^i—Ca1—C6	158.30 (4)	C17—C22—H22	119.9
N2—Ca1—C6	21.70 (4)	C12A—C11A—C15A	119.3 (7)
C4—Ca1—C6	48.24 (4)	C12A—C11A—C5	124.0 (11)
C4^i—Ca1—C6	131.76 (4)	C15A—C11A—C5	116.7 (11)
C1—Ca1—C6	89.80 (4)	C11A—C12A—C13A	118.8 (10)
C1^i—Ca1—C6	90.20 (4)	C11A—C12A—H12A	120.6
N1^i—Ca1—C6^i	69.43 (4)	C13A—C12A—H12A	120.6
N1—Ca1—C6^i	110.57 (4)	N3A—C13A—C12A	120.8 (10)
N2^i—Ca1—C6^i	21.70 (4)	N3A—C13A—H13A	119.6
N2—Ca1—C6^i	158.30 (4)	C12A—C13A—H13A	119.6
C4—Ca1—C6^i	131.76 (4)	C13A—N3A—C14A	120.6 (9)
C4^i—Ca1—C6^i	48.24 (4)	C13A—N3A—C16A	122.0 (10)
C1—Ca1—C6^i	90.20 (4)	C14A—N3A—C16A	117.4 (9)
C1^i—Ca1—C6^i	89.80 (4)	N3A—C14A—C15A	121.6 (10)
C6—Ca1—C6^i	180.0	N3A—C14A—H14A	119.2
N1^i—Ca1—C9^i	111.96 (4)	C15A—C14A—H14A	119.2
N1—Ca1—C9^i	68.04 (4)	C14A—C15A—C11A	118.8 (10)
N2^i—Ca1—C9^i	20.90 (4)	C14A—C15A—H15A	120.6
N2—Ca1—C9^i	159.10 (4)	C11A—C15A—H15A	120.6
C4—Ca1—C9^i	89.23 (4)	C17A—C16A—N3A	110.8 (6)
C4^i—Ca1—C9^i	90.77 (4)	C17A—C16A—H16C	109.5
C1—Ca1—C9^i	47.66 (4)	N3A—C16A—H16C	109.5
C1^i—Ca1—C9^i	132.34 (4)	C17A—C16A—H16D	109.5
C6—Ca1—C9^i	137.46 (4)	N3A—C16A—H16D	109.5
C6^i—Ca1—C9^i	42.54 (4)	H16C—C16A—H16D	108.1
N1^i—Ca1—C9	68.04 (4)	C18A—C17A—C22A	120.9 (9)
N1—Ca1—C9	111.96 (4)	C18A—C17A—C16A	119.4 (8)
N2^i—Ca1—C9	159.10 (4)	C22A—C17A—C16A	119.7 (8)
N2—Ca1—C9	20.90 (4)	C19A—C18A—C17A	117.5 (8)
C4—Ca1—C9	90.77 (4)	C19A—C18A—H18A	121.2
C4^i—Ca1—C9	89.23 (4)	C17A—C18A—H18A	121.2
C1—Ca1—C9	132.34 (4)	C18A—C19A—C20A	122.3 (9)
C1^i—Ca1—C9	47.66 (4)	C18A—C19A—H19A	118.8
C6—Ca1—C9	42.54 (4)	C20A—C19A—H19A	118.8
C6^i—Ca1—C9	137.46 (4)	C19A—C20A—C21A	120.1 (11)
C9^i—Ca1—C9	180.0	C19A—C20A—H20A	119.9
N1^i—Ca1—H2A	87.9 (10)	C21A—C20A—H20A	119.9
N1—Ca1—H2A	92.1 (10)	C20A—C21A—C22A	118.5 (11)
N2^i—Ca1—H2A	175.7 (10)	C20A—C21A—H21A	120.8
N2—Ca1—H2A	4.3 (10)	C22A—C21A—H21A	120.8
C4—Ca1—H2A	71.0 (10)	C21A—C22A—C17A	120.6 (10)
C4^i—Ca1—H2A	109.0 (10)	C21A—C22A—H22A	119.7
C1—Ca1—H2A	112.4 (10)	C17A—C22A—H22A	119.7
C1^i—Ca1—H2A	67.6 (10)	C24—C23—C27	117.68 (14)
C6—Ca1—H2A	23.3 (10)	C24—C23—C10	121.39 (13)
C6^i—Ca1—H2A	156.7 (10)	C27—C23—C10	120.90 (14)
C9^i—Ca1—H2A	159.5 (10)	C25—C24—C23	119.84 (15)
C9—Ca1—H2A	20.5 (10)	C25—C24—H24	120.1
N1^i—Ca1—H2A^i	92.1 (10)	C23—C24—H24	120.1
N1—Ca1—H2A^i	87.9 (10)	N4—C25—C24	121.13 (15)
N2^i—Ca1—H2A^i	4.3 (10)	N4—C25—H25	119.4
N2—Ca1—H2A^i	175.7 (10)	C24—C25—H25	119.4
C4—Ca1—H2A^i	109.0 (10)	N4—C26—C27	120.45 (15)
C4^i—Ca1—H2A^i	71.0 (10)	N4—C26—H26	119.8
C1—Ca1—H2A^i	67.6 (10)	C27—C26—H26	119.8
C1^i—Ca1—H2A^i	112.4 (10)	C26—C27—C23	120.22 (15)
C6—Ca1—H2A^i	156.7 (10)	C26—C27—H27	119.9
C6^i—Ca1—H2A^i	23.3 (10)	C23—C27—H27	119.9
C9^i—Ca1—H2A^i	20.5 (10)	N4—C28—C29	113.42 (14)
C9—Ca1—H2A^i	159.5 (10)	N4—C28—H28A	108.9
H2A—Ca1—H2A^i	179.997 (11)	C29—C28—H28A	108.9
H7A—O7—H7B	107 (2)	N4—C28—H28B	108.9
H8A—O8—H8B	106 (2)	C29—C28—H28B	108.9
C4—N1—C1	105.18 (12)	H28A—C28—H28B	107.7
C4—N1—Ca1	126.33 (9)	C34—C29—C30	118.72 (17)
C1—N1—Ca1	128.43 (9)	C34—C29—C28	124.18 (15)
C9—N2—C6	109.83 (12)	C30—C29—C28	117.05 (16)
C9—N2—Ca1	126.02 (10)	C31—C30—C29	120.4 (2)
C6—N2—Ca1	123.91 (10)	C31—C30—H30	119.8
C9—N2—H2A	124.5 (16)	C29—C30—H30	119.8
C6—N2—H2A	125.6 (16)	C32—C31—C30	120.5 (2)
Ca1—N2—H2A	6.5 (16)	C32—C31—H31	119.7
C25—N4—C26	120.56 (13)	C30—C31—H31	119.7
C25—N4—C28	119.98 (14)	C31—C32—C33	119.8 (2)
C26—N4—C28	119.45 (14)	C31—C32—H32	120.1
N1—C1—C10^i	125.15 (13)	C33—C32—H32	120.1
N1—C1—C2	110.75 (12)	C32—C33—C34	120.1 (2)
C10^i—C1—C2	124.10 (13)	C32—C33—H33	119.9
N1—C1—Ca1	31.17 (6)	C34—C33—H33	119.9
C10^i—C1—Ca1	94.03 (9)	C29—C34—C33	120.40 (18)
C2—C1—Ca1	141.80 (10)	C29—C34—H34	119.8
C3—C2—C1	106.57 (13)	C33—C34—H34	119.8
C3—C2—H2	126.7	F1—C35—F2	108.2 (6)
C1—C2—H2	126.7	F1—C35—F3	104.9 (6)
C2—C3—C4	106.74 (13)	F2—C35—F3	105.2 (6)
C2—C3—H3	126.6	F1—C35—S1	113.0 (5)
C4—C3—H3	126.6	F2—C35—S1	112.3 (5)
N1—C4—C5	125.51 (13)	F3—C35—S1	112.7 (5)
N1—C4—C3	110.74 (12)	O3—S1—O2	116.5 (4)
C5—C4—C3	123.71 (13)	O3—S1—O1	112.6 (4)
N1—C4—Ca1	32.48 (6)	O2—S1—O1	117.0 (4)
C5—C4—Ca1	93.04 (9)	O3—S1—C35	102.7 (3)
C3—C4—Ca1	143.12 (10)	O2—S1—C35	103.6 (4)
C6—C5—C4	126.87 (13)	O1—S1—C35	101.5 (3)
C6—C5—C11A	116.8 (5)	F3A—C35A—F2A	109.1 (9)
C4—C5—C11A	116.3 (5)	F3A—C35A—F1A	106.1 (8)
C6—C5—C11	116.3 (3)	F2A—C35A—F1A	106.4 (8)
C4—C5—C11	116.9 (3)	F3A—C35A—S1A	110.9 (7)
N2—C6—C5	126.11 (13)	F2A—C35A—S1A	110.8 (7)
N2—C6—C7	106.85 (12)	F1A—C35A—S1A	113.3 (7)
C5—C6—C7	127.05 (13)	O1A—S1A—O3A	116.9 (5)
N2—C6—Ca1	34.39 (6)	O1A—S1A—O2A	117.0 (6)
C5—C6—Ca1	91.84 (9)	O3A—S1A—O2A	108.3 (5)
C7—C6—Ca1	141.01 (10)	O1A—S1A—C35A	107.0 (5)
C8—C7—C6	108.46 (13)	O3A—S1A—C35A	103.0 (5)
C8—C7—H7	125.8	O2A—S1A—C35A	102.6 (5)
C6—C7—H7	125.8	F6—C36—F5	99.7 (8)
C7—C8—C9	107.86 (13)	F6—C36—F4	107.6 (7)
C7—C8—H8	126.1	F5—C36—F4	105.0 (7)
C9—C8—H8	126.1	F6—C36—S2	114.6 (6)
N2—C9—C10	125.80 (13)	F5—C36—S2	112.5 (6)
N2—C9—C8	107.00 (13)	F4—C36—S2	115.9 (6)
C10—C9—C8	127.17 (14)	O6—S2—O5	114.3 (6)
N2—C9—Ca1	33.08 (6)	O6—S2—O4	116.6 (7)
C10—C9—Ca1	92.77 (9)	O5—S2—O4	114.4 (7)
C8—C9—Ca1	139.84 (10)	O6—S2—C36	105.0 (6)
C9—C10—C1^i	125.54 (13)	O5—S2—C36	102.0 (4)
C9—C10—C23	116.15 (13)	O4—S2—C36	101.9 (7)
C1^i—C10—C23	118.29 (13)	F5A—C36A—F6A	118.7 (9)
C12—C11—C15	116.5 (5)	F5A—C36A—F4A	100.2 (8)
C12—C11—C5	118.1 (7)	F6A—C36A—F4A	105.6 (9)
C15—C11—C5	125.4 (7)	F5A—C36A—S2A	112.2 (8)
C13—C12—C11	120.9 (6)	F6A—C36A—S2A	111.7 (7)
C13—C12—H12	119.5	F4A—C36A—S2A	106.8 (7)
C11—C12—H12	119.5	O4A—S2A—O6A	117.2 (8)
N3—C13—C12	121.0 (6)	O4A—S2A—O5A	111.6 (6)
N3—C13—H13	119.5	O6A—S2A—O5A	113.6 (8)
C12—C13—H13	119.5	O4A—S2A—C36A	106.8 (6)
C13—N3—C14	120.4 (6)	O6A—S2A—C36A	107.2 (8)
C13—N3—C16	120.1 (5)	O5A—S2A—C36A	98.2 (6)
C4—N1—C1—C10^i	−179.03 (14)	C6—C5—C11A—C15A	73.1 (8)
Ca1—N1—C1—C10^i	3.8 (2)	C4—C5—C11A—C15A	−108.5 (7)
C4—N1—C1—C2	1.37 (17)	C15A—C11A—C12A—C13A	0.0 (3)
Ca1—N1—C1—C2	−175.84 (10)	C5—C11A—C12A—C13A	−179.5 (11)
C4—N1—C1—Ca1	177.21 (18)	C11A—C12A—C13A—N3A	−0.1 (3)
N1—C1—C2—C3	−1.34 (18)	C12A—C13A—N3A—C14A	0.6 (6)
C10^i—C1—C2—C3	179.06 (15)	C12A—C13A—N3A—C16A	−179.9 (10)
Ca1—C1—C2—C3	−4.8 (2)	C13A—N3A—C14A—C15A	−0.9 (8)
C1—C2—C3—C4	0.71 (18)	C16A—N3A—C14A—C15A	179.6 (9)
C1—N1—C4—C5	−178.69 (14)	N3A—C14A—C15A—C11A	0.7 (8)
Ca1—N1—C4—C5	−1.4 (2)	C12A—C11A—C15A—C14A	−0.2 (6)
C1—N1—C4—C3	−0.93 (16)	C5—C11A—C15A—C14A	179.3 (10)
Ca1—N1—C4—C3	176.37 (10)	C13A—N3A—C16A—C17A	103.7 (9)
C1—N1—C4—Ca1	−177.29 (17)	C14A—N3A—C16A—C17A	−76.7 (10)
C2—C3—C4—N1	0.11 (18)	N3A—C16A—C17A—C18A	−95.8 (8)
C2—C3—C4—C5	177.93 (15)	N3A—C16A—C17A—C22A	84.5 (8)
C2—C3—C4—Ca1	3.4 (2)	C22A—C17A—C18A—C19A	−0.2 (4)
N1—C4—C5—C6	1.8 (2)	C16A—C17A—C18A—C19A	−179.9 (3)
C3—C4—C5—C6	−175.64 (15)	C17A—C18A—C19A—C20A	−0.2 (6)
Ca1—C4—C5—C6	1.09 (16)	C18A—C19A—C20A—C21A	0.2 (8)
N1—C4—C5—C11A	−176.3 (7)	C19A—C20A—C21A—C22A	0.3 (8)
C3—C4—C5—C11A	6.2 (7)	C20A—C21A—C22A—C17A	−0.8 (8)
Ca1—C4—C5—C11A	−177.1 (7)	C18A—C17A—C22A—C21A	0.8 (6)
N1—C4—C5—C11	−177.6 (4)	C16A—C17A—C22A—C21A	−179.5 (4)
C3—C4—C5—C11	4.9 (5)	C9—C10—C23—C24	60.9 (2)
Ca1—C4—C5—C11	−178.4 (4)	C1^i—C10—C23—C24	−120.65 (17)
C9—N2—C6—C5	−179.82 (15)	C9—C10—C23—C27	−116.97 (17)
Ca1—N2—C6—C5	5.5 (2)	C1^i—C10—C23—C27	61.4 (2)
C9—N2—C6—C7	0.13 (17)	C27—C23—C24—C25	4.0 (2)
Ca1—N2—C6—C7	−174.54 (11)	C10—C23—C24—C25	−174.02 (15)
C9—N2—C6—Ca1	174.66 (18)	C26—N4—C25—C24	−1.1 (3)
C4—C5—C6—N2	−4.2 (3)	C28—N4—C25—C24	177.82 (16)
C11A—C5—C6—N2	174.0 (7)	C23—C24—C25—N4	−2.1 (3)
C11—C5—C6—N2	175.3 (4)	C25—N4—C26—C27	2.3 (3)
C4—C5—C6—C7	175.87 (16)	C28—N4—C26—C27	−176.68 (16)
C11A—C5—C6—C7	−6.0 (7)	N4—C26—C27—C23	−0.2 (3)
C11—C5—C6—C7	−4.7 (5)	C24—C23—C27—C26	−2.8 (3)
C4—C5—C6—Ca1	−1.08 (16)	C10—C23—C27—C26	175.14 (16)
C11A—C5—C6—Ca1	177.1 (7)	C25—N4—C28—C29	93.82 (19)
C11—C5—C6—Ca1	178.4 (4)	C26—N4—C28—C29	−87.2 (2)
N2—C6—C7—C8	0.26 (19)	N4—C28—C29—C34	−17.9 (2)
C5—C6—C7—C8	−179.80 (16)	N4—C28—C29—C30	164.71 (16)
Ca1—C6—C7—C8	−4.6 (2)	C34—C29—C30—C31	0.5 (3)
C6—C7—C8—C9	−0.5 (2)	C28—C29—C30—C31	178.00 (18)
C6—N2—C9—C10	−178.49 (15)	C29—C30—C31—C32	−0.6 (3)
Ca1—N2—C9—C10	−4.0 (2)	C30—C31—C32—C33	0.0 (3)
C6—N2—C9—C8	−0.44 (17)	C31—C32—C33—C34	0.8 (3)
Ca1—N2—C9—C8	174.08 (11)	C30—C29—C34—C33	0.3 (3)
C6—N2—C9—Ca1	−174.52 (19)	C28—C29—C34—C33	−177.04 (18)
C7—C8—C9—N2	0.60 (19)	C32—C33—C34—C29	−0.9 (3)
C7—C8—C9—C10	178.62 (16)	F1—C35—S1—O3	−69.7 (7)
C7—C8—C9—Ca1	5.6 (2)	F2—C35—S1—O3	53.1 (7)
N2—C9—C10—C1^i	1.6 (3)	F3—C35—S1—O3	171.7 (6)
C8—C9—C10—C1^i	−176.11 (16)	F1—C35—S1—O2	52.1 (7)
Ca1—C9—C10—C1^i	−0.62 (16)	F2—C35—S1—O2	174.8 (6)
N2—C9—C10—C23	179.82 (14)	F3—C35—S1—O2	−66.6 (6)
C8—C9—C10—C23	2.2 (2)	F1—C35—S1—O1	173.8 (6)
Ca1—C9—C10—C23	177.66 (11)	F2—C35—S1—O1	−63.5 (7)
C6—C5—C11—C12	−95.2 (5)	F3—C35—S1—O1	55.1 (6)
C4—C5—C11—C12	84.3 (5)	F3A—C35A—S1A—O1A	64.2 (9)
C6—C5—C11—C15	86.8 (6)	F2A—C35A—S1A—O1A	−57.0 (9)
C4—C5—C11—C15	−93.7 (6)	F1A—C35A—S1A—O1A	−176.5 (7)
C15—C11—C12—C13	−0.4 (2)	F3A—C35A—S1A—O3A	−171.9 (8)
C5—C11—C12—C13	−178.7 (6)	F2A—C35A—S1A—O3A	66.8 (9)
C11—C12—C13—N3	−0.6 (3)	F1A—C35A—S1A—O3A	−52.7 (9)
C12—C13—N3—C14	1.5 (5)	F3A—C35A—S1A—O2A	−59.5 (10)
C12—C13—N3—C16	−173.5 (6)	F2A—C35A—S1A—O2A	179.3 (8)
C13—N3—C14—C15	−1.3 (6)	F1A—C35A—S1A—O2A	59.8 (9)
C16—N3—C14—C15	173.8 (6)	F6—C36—S2—O6	−58.2 (7)
N3—C14—C15—C11	0.2 (6)	F5—C36—S2—O6	−171.1 (8)
C12—C11—C15—C14	0.6 (5)	F4—C36—S2—O6	68.1 (9)
C5—C11—C15—C14	178.7 (7)	F6—C36—S2—O5	61.3 (7)
C13—N3—C16—C17	101.8 (6)	F5—C36—S2—O5	−51.6 (8)
C14—N3—C16—C17	−73.2 (6)	F4—C36—S2—O5	−172.4 (8)
N3—C16—C17—C22	94.9 (5)	F6—C36—S2—O4	179.7 (8)
N3—C16—C17—C18	−84.8 (4)	F5—C36—S2—O4	66.9 (9)
C22—C17—C18—C19	−0.2 (3)	F4—C36—S2—O4	−54.0 (10)
C16—C17—C18—C19	179.5 (2)	F5A—C36A—S2A—O4A	−83.9 (9)
C17—C18—C19—C20	0.6 (5)	F6A—C36A—S2A—O4A	52.2 (10)
C18—C19—C20—C21	0.1 (7)	F4A—C36A—S2A—O4A	167.3 (8)
C19—C20—C21—C22	−1.3 (7)	F5A—C36A—S2A—O6A	42.6 (11)
C20—C21—C22—C17	1.8 (7)	F6A—C36A—S2A—O6A	178.7 (10)
C18—C17—C22—C21	−1.0 (5)	F4A—C36A—S2A—O6A	−66.3 (10)
C16—C17—C22—C21	179.3 (3)	F5A—C36A—S2A—O5A	160.5 (8)
C6—C5—C11A—C12A	−107.4 (8)	F6A—C36A—S2A—O5A	−63.4 (9)
C4—C5—C11A—C12A	70.9 (8)	F4A—C36A—S2A—O5A	51.6 (8)

Symmetry code: (i) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O1	0.86 (2)	2.04 (2)	2.817 (5)	150 (3)
O7—H7A···O3A	0.86 (2)	2.14 (2)	2.874 (6)	143 (3)
O7—H7B···O4	0.88 (2)	2.24 (3)	2.965 (11)	140 (3)
O7—H7B···O6A	0.88 (2)	2.29 (3)	3.048 (10)	144 (3)
O8—H8A···O2^ii	0.87 (2)	2.08 (2)	2.914 (6)	163 (3)
O8—H8A···O2A^ii	0.87 (2)	1.94 (2)	2.789 (7)	167 (3)
O8—H8B···O7	0.89 (2)	1.96 (2)	2.838 (3)	174 (3)

Symmetry code: (ii) −x+2, y−1/2, −z+3/2.