Crystal structure of bis­(4-meth­oxy­pyridine-κN)(meso-5,10,15,20-tetra­phenyl­porphyrinato-κ⁴N,N′,N′′,N′′′)iron(III) perchlorate

In the crystal structure of the title compound, the Fe^III ions are octa­hedrally coordinated by four N atoms of a porphyrin moiety as well as two 4-meth­oxy­pyridine ligands into discrete complexes that are charge-balanced by perchlorate anions.

Key indicators

• Single-crystal X-ray study
• T = 170 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in solvent or counterion
• R factor = 0.040
• wR factor = 0.099
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H36C     ..O1       .       2.64 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      5.202 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         26 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....         17 Note

Alert level G
PLAT012_ALERT_1_G N.O.K.   _shelx_res_checksum Found in CIF ......     Please Check
PLAT300_ALERT_4_G Atom Site Occupancy of Cl1        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of O2         Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of O3         Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of O4         Constrained at        0.5 Check
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  2  )        80% Note
PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) .       1.24 Ratio
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #        118 Check
              O4   -CL1  -O2      3.655   1.555   1.555             21.90 Deg.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #        120 Check
              O2   -CL1  -O4      3.655   1.555   1.555             21.80 Deg.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #        134 Check
              CL1  -CL1  -O3      3.655   1.555   3.655              9.80 Deg.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #        141 Check
              CL1  -O1   -CL1     1.555   1.555   3.655             20.54 Deg.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #        144 Check
              CL1  -O2   -CL1     3.655   1.555   1.555             21.61 Deg.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #        145 Check
              CL1  -O3   -CL1     1.555   1.555   3.655              3.54 Deg.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #        148 Check
              CL1  -O4   -CL1     3.655   1.555   1.555             21.53 Deg.
PLAT794_ALERT_5_G Tentative Bond Valency for Fe1       (III)     .       3.59 Info
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          9 Info

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

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

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2008); cell refinement: X-AREA (Stoe & Cie, 2008); data reduction: X-AREA (Stoe & Cie, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: XP (Sheldrick, 2008) and DIAMOND (Brandenburg, 2014); software used to prepare material for publication: publCIF (Westrip, 2010).

Bis(4-methoxypyridine-κN)(meso-5,10,15,20-tetraphenylporphyrinato-κ⁴N,N',N'',N''')iron(III) perchlorate

Crystal data

[Fe(C44H28N4)(C6H7NO)2]ClO4	Dx = 1.416 Mg m^−3
Mr = 986.25	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbcn	Cell parameters from 36542 reflections
a = 16.9772 (4) Å	θ = 1.7–27.0°
b = 11.1879 (2) Å	µ = 0.45 mm^−1
c = 24.3484 (6) Å	T = 170 K
V = 4624.72 (18) Å^3	Block, colorless
Z = 4	0.12 × 0.10 × 0.09 mm
F(000) = 2044

Data collection

STOE IPDS-2 diffractometer	Rint = 0.033
ω scans	θmax = 27.0°, θmin = 1.7°
36542 measured reflections	h = −21→21
5029 independent reflections	k = −13→14
4454 reflections with I > 2σ(I)	l = −29→31

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.099	w = 1/[σ^2(Fo^2) + (0.0472P)^2 + 2.1988P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
5029 reflections	Δρmax = 0.28 e Å^−3
337 parameters	Δρmin = −0.48 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)
Fe1	0.5000	0.5000	0.5000	0.02670 (10)
N1	0.51998 (8)	0.59036 (13)	0.43056 (5)	0.0287 (3)
N2	0.38550 (8)	0.53845 (13)	0.49210 (5)	0.0285 (3)
C1	0.66431 (9)	0.56717 (15)	0.42585 (6)	0.0303 (3)
C2	0.59265 (9)	0.61091 (16)	0.40705 (7)	0.0312 (3)
C3	0.58436 (10)	0.68660 (18)	0.36008 (7)	0.0386 (4)
H3	0.6257	0.7136	0.3369	0.046*
C4	0.50747 (10)	0.71259 (17)	0.35457 (7)	0.0374 (4)
H4	0.4844	0.7618	0.3271	0.045*
C5	0.46682 (9)	0.65166 (15)	0.39806 (6)	0.0301 (3)
C6	0.38565 (9)	0.65732 (15)	0.40647 (6)	0.0294 (3)
C7	0.34876 (9)	0.60222 (15)	0.45098 (6)	0.0295 (3)
C8	0.26493 (9)	0.60202 (16)	0.45999 (7)	0.0322 (3)
H8	0.2263	0.6386	0.4373	0.039*
C9	0.25149 (10)	0.54030 (17)	0.50662 (7)	0.0332 (3)
H9	0.2016	0.5257	0.5230	0.040*
C10	0.32645 (9)	0.50074 (15)	0.52689 (7)	0.0293 (3)
C11	0.33579 (9)	0.72443 (15)	0.36631 (6)	0.0294 (3)
C12	0.33009 (10)	0.68687 (16)	0.31184 (7)	0.0341 (4)
H12	0.3600	0.6203	0.2996	0.041*
C13	0.28082 (10)	0.74660 (19)	0.27552 (7)	0.0390 (4)
H13	0.2768	0.7199	0.2386	0.047*
C14	0.23762 (10)	0.84445 (19)	0.29253 (8)	0.0415 (4)
H14	0.2040	0.8849	0.2675	0.050*
C15	0.24377 (10)	0.88294 (17)	0.34625 (8)	0.0395 (4)
H15	0.2145	0.9506	0.3581	0.047*
C16	0.29235 (10)	0.82350 (16)	0.38300 (7)	0.0341 (4)
H16	0.2960	0.8506	0.4199	0.041*
C17	0.73642 (9)	0.59461 (16)	0.39261 (7)	0.0312 (3)
C18	0.76060 (12)	0.51717 (19)	0.35181 (8)	0.0437 (4)
H18	0.7316	0.4461	0.3450	0.052*
C19	0.82706 (12)	0.5424 (2)	0.32064 (9)	0.0500 (5)
H19	0.8438	0.4878	0.2931	0.060*
C20	0.86880 (10)	0.6461 (2)	0.32953 (8)	0.0434 (4)
H20	0.9137	0.6640	0.3077	0.052*
C21	0.84516 (11)	0.72356 (19)	0.37005 (9)	0.0460 (5)
H21	0.8740	0.7950	0.3764	0.055*
C22	0.77939 (11)	0.69788 (18)	0.40173 (8)	0.0423 (4)
H22	0.7637	0.7516	0.4299	0.051*
N31	0.48297 (8)	0.34725 (13)	0.45758 (6)	0.0299 (3)
C31	0.50607 (12)	0.23963 (17)	0.47644 (8)	0.0420 (4)
H31	0.5320	0.2360	0.5110	0.050*
C32	0.49415 (13)	0.13525 (18)	0.44838 (8)	0.0457 (5)
H32	0.5116	0.0614	0.4633	0.055*
C33	0.45604 (11)	0.13819 (16)	0.39757 (7)	0.0363 (4)
C34	0.43316 (10)	0.24801 (16)	0.37747 (7)	0.0351 (4)
H34	0.4077	0.2541	0.3429	0.042*
C35	0.44775 (10)	0.34847 (16)	0.40822 (7)	0.0342 (4)
H35	0.4319	0.4235	0.3937	0.041*
O31	0.44631 (9)	0.03299 (12)	0.37175 (6)	0.0467 (3)
C36	0.41268 (13)	0.03669 (19)	0.31772 (8)	0.0461 (5)
H36A	0.3605	0.0738	0.3194	0.069*
H36B	0.4078	−0.0448	0.3034	0.069*
H36C	0.4468	0.0836	0.2934	0.069*
Cl1	0.51249 (9)	0.41187 (7)	0.25605 (9)	0.0354 (3)	0.5
O1	0.5000	0.28459 (18)	0.2500	0.0480 (5)
O2	0.4431 (3)	0.4585 (8)	0.2775 (3)	0.084 (3)	0.5
O3	0.5724 (2)	0.4344 (3)	0.29567 (16)	0.0722 (10)	0.5
O4	0.5362 (5)	0.4650 (9)	0.2069 (3)	0.095 (3)	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.02464 (16)	0.02978 (17)	0.02567 (16)	0.00148 (12)	0.00190 (11)	0.00273 (12)
N1	0.0254 (6)	0.0324 (7)	0.0282 (6)	0.0014 (5)	0.0020 (5)	0.0033 (5)
N2	0.0259 (6)	0.0325 (7)	0.0272 (6)	0.0018 (5)	0.0017 (5)	0.0032 (5)
C1	0.0285 (7)	0.0334 (9)	0.0292 (8)	0.0003 (6)	0.0032 (6)	0.0012 (6)
C2	0.0294 (8)	0.0347 (9)	0.0296 (8)	0.0003 (6)	0.0044 (6)	0.0042 (7)
C3	0.0323 (8)	0.0479 (11)	0.0357 (9)	0.0010 (7)	0.0057 (7)	0.0118 (8)
C4	0.0324 (8)	0.0431 (10)	0.0367 (9)	0.0022 (7)	0.0018 (7)	0.0116 (8)
C5	0.0296 (8)	0.0327 (9)	0.0281 (7)	0.0023 (6)	0.0002 (6)	0.0047 (6)
C6	0.0294 (7)	0.0302 (8)	0.0288 (7)	0.0025 (6)	0.0003 (6)	0.0005 (6)
C7	0.0276 (7)	0.0322 (8)	0.0286 (8)	0.0023 (6)	−0.0011 (6)	0.0005 (6)
C8	0.0269 (8)	0.0377 (9)	0.0321 (8)	0.0034 (7)	−0.0008 (6)	0.0029 (7)
C9	0.0264 (7)	0.0382 (9)	0.0349 (8)	0.0020 (7)	0.0022 (6)	0.0019 (7)
C10	0.0263 (7)	0.0322 (8)	0.0293 (8)	0.0006 (6)	0.0022 (6)	0.0003 (6)
C11	0.0268 (7)	0.0315 (8)	0.0300 (8)	0.0003 (6)	0.0004 (6)	0.0044 (6)
C12	0.0339 (8)	0.0364 (9)	0.0321 (8)	0.0007 (7)	0.0021 (6)	0.0016 (7)
C13	0.0348 (8)	0.0528 (11)	0.0294 (8)	−0.0045 (8)	−0.0030 (7)	0.0058 (8)
C14	0.0305 (8)	0.0516 (11)	0.0424 (9)	0.0022 (8)	−0.0026 (7)	0.0168 (9)
C15	0.0325 (8)	0.0375 (10)	0.0486 (10)	0.0074 (7)	0.0047 (8)	0.0096 (8)
C16	0.0334 (8)	0.0351 (9)	0.0339 (8)	0.0019 (7)	0.0024 (7)	0.0022 (7)
C17	0.0262 (7)	0.0366 (9)	0.0309 (8)	0.0020 (6)	0.0014 (6)	0.0063 (7)
C18	0.0439 (10)	0.0459 (11)	0.0414 (10)	−0.0082 (8)	0.0113 (8)	−0.0035 (8)
C19	0.0459 (11)	0.0614 (13)	0.0427 (10)	−0.0035 (10)	0.0156 (8)	−0.0055 (10)
C20	0.0288 (8)	0.0622 (13)	0.0394 (9)	−0.0021 (8)	0.0052 (7)	0.0110 (9)
C21	0.0332 (9)	0.0473 (11)	0.0574 (12)	−0.0083 (8)	0.0014 (8)	0.0054 (9)
C22	0.0356 (9)	0.0424 (10)	0.0489 (10)	−0.0017 (8)	0.0081 (8)	−0.0037 (8)
N31	0.0284 (6)	0.0325 (7)	0.0289 (6)	0.0019 (5)	0.0009 (5)	0.0019 (6)
C31	0.0550 (11)	0.0366 (10)	0.0342 (9)	0.0036 (8)	−0.0073 (8)	0.0035 (7)
C32	0.0652 (13)	0.0338 (10)	0.0381 (10)	0.0025 (9)	−0.0075 (9)	0.0052 (8)
C33	0.0404 (9)	0.0330 (9)	0.0355 (9)	−0.0041 (7)	0.0010 (7)	0.0001 (7)
C34	0.0341 (8)	0.0388 (9)	0.0324 (8)	0.0020 (7)	−0.0034 (7)	0.0005 (7)
C35	0.0352 (8)	0.0349 (9)	0.0325 (8)	0.0040 (7)	−0.0017 (6)	0.0021 (7)
O31	0.0652 (9)	0.0333 (7)	0.0416 (7)	−0.0056 (6)	−0.0088 (6)	−0.0011 (6)
C36	0.0558 (12)	0.0411 (10)	0.0413 (10)	−0.0094 (9)	−0.0083 (9)	−0.0030 (8)
Cl1	0.0332 (11)	0.0327 (3)	0.0404 (10)	0.0001 (4)	0.0032 (6)	−0.0014 (4)
O1	0.0637 (13)	0.0331 (10)	0.0472 (11)	0.000	−0.0063 (9)	0.000
O2	0.044 (2)	0.053 (3)	0.154 (8)	0.0169 (19)	0.050 (3)	−0.008 (4)
O3	0.066 (2)	0.067 (2)	0.083 (2)	−0.0006 (18)	−0.0318 (19)	−0.0234 (19)
O4	0.184 (9)	0.051 (3)	0.050 (3)	−0.006 (5)	0.049 (4)	0.006 (2)

Geometric parameters (Å, º)

Fe1—N1^i	1.9988 (13)	C17—C22	1.384 (3)
Fe1—N1	1.9989 (13)	C18—C19	1.389 (3)
Fe1—N2^i	2.0002 (13)	C18—H18	0.9500
Fe1—N2	2.0003 (13)	C19—C20	1.377 (3)
Fe1—N31	2.0177 (14)	C19—H19	0.9500
Fe1—N31^i	2.0177 (14)	C20—C21	1.373 (3)
N1—C2	1.379 (2)	C20—H20	0.9500
N1—C5	1.382 (2)	C21—C22	1.387 (3)
N2—C10	1.379 (2)	C21—H21	0.9500
N2—C7	1.379 (2)	C22—H22	0.9500
C1—C10^i	1.388 (2)	N31—C35	1.342 (2)
C1—C2	1.389 (2)	N31—C31	1.347 (2)
C1—C17	1.499 (2)	C31—C32	1.368 (3)
C2—C3	1.430 (2)	C31—H31	0.9500
C3—C4	1.344 (2)	C32—C33	1.397 (3)
C3—H3	0.9500	C32—H32	0.9500
C4—C5	1.436 (2)	C33—O31	1.344 (2)
C4—H4	0.9500	C33—C34	1.378 (3)
C5—C6	1.395 (2)	C34—C35	1.373 (3)
C6—C7	1.395 (2)	C34—H34	0.9500
C6—C11	1.495 (2)	C35—H35	0.9500
C7—C8	1.440 (2)	O31—C36	1.435 (2)
C8—C9	1.348 (2)	C36—H36A	0.9800
C8—H8	0.9500	C36—H36B	0.9800
C9—C10	1.435 (2)	C36—H36C	0.9800
C9—H9	0.9500	Cl1—Cl1^ii	0.5162 (19)
C10—C1^i	1.388 (2)	Cl1—O2^ii	1.228 (6)
C11—C16	1.392 (2)	Cl1—O4^ii	1.361 (8)
C11—C12	1.395 (2)	Cl1—O2	1.391 (5)
C12—C13	1.389 (2)	Cl1—O4	1.396 (8)
C12—H12	0.9500	Cl1—O3	1.425 (3)
C13—C14	1.381 (3)	Cl1—O1	1.447 (2)
C13—H13	0.9500	Cl1—O3^ii	1.931 (3)
C14—C15	1.381 (3)	O1—Cl1^ii	1.447 (2)
C14—H14	0.9500	O2—O4^ii	0.524 (14)
C15—C16	1.387 (2)	O2—Cl1^ii	1.228 (6)
C15—H15	0.9500	O3—Cl1^ii	1.931 (3)
C16—H16	0.9500	O4—O2^ii	0.524 (14)
C17—C18	1.381 (3)	O4—Cl1^ii	1.361 (8)
N1^i—Fe1—N1	180.00 (4)	C19—C18—H18	119.8
N1^i—Fe1—N2^i	88.56 (5)	C20—C19—C18	120.21 (19)
N1—Fe1—N2^i	91.44 (5)	C20—C19—H19	119.9
N1^i—Fe1—N2	91.44 (5)	C18—C19—H19	119.9
N1—Fe1—N2	88.56 (5)	C21—C20—C19	119.64 (17)
N2^i—Fe1—N2	180.00 (8)	C21—C20—H20	120.2
N1^i—Fe1—N31	88.87 (6)	C19—C20—H20	120.2
N1—Fe1—N31	91.13 (5)	C20—C21—C22	120.27 (19)
N2^i—Fe1—N31	90.36 (6)	C20—C21—H21	119.9
N2—Fe1—N31	89.64 (6)	C22—C21—H21	119.9
N1^i—Fe1—N31^i	91.13 (5)	C17—C22—C21	120.52 (18)
N1—Fe1—N31^i	88.87 (6)	C17—C22—H22	119.7
N2^i—Fe1—N31^i	89.64 (6)	C21—C22—H22	119.7
N2—Fe1—N31^i	90.36 (6)	C35—N31—C31	116.36 (15)
N31—Fe1—N31^i	180.0	C35—N31—Fe1	120.90 (12)
C2—N1—C5	105.28 (13)	C31—N31—Fe1	122.74 (12)
C2—N1—Fe1	125.95 (11)	N31—C31—C32	123.34 (17)
C5—N1—Fe1	128.63 (11)	N31—C31—H31	118.3
C10—N2—C7	106.01 (13)	C32—C31—H31	118.3
C10—N2—Fe1	125.58 (11)	C31—C32—C33	119.39 (18)
C7—N2—Fe1	128.37 (11)	C31—C32—H32	120.3
C10^i—C1—C2	124.42 (15)	C33—C32—H32	120.3
C10^i—C1—C17	117.87 (14)	O31—C33—C34	125.44 (16)
C2—C1—C17	117.71 (14)	O31—C33—C32	116.77 (17)
N1—C2—C1	126.01 (15)	C34—C33—C32	117.78 (17)
N1—C2—C3	110.04 (14)	C35—C34—C33	119.04 (16)
C1—C2—C3	123.95 (15)	C35—C34—H34	120.5
C4—C3—C2	107.67 (15)	C33—C34—H34	120.5
C4—C3—H3	126.2	N31—C35—C34	124.07 (16)
C2—C3—H3	126.2	N31—C35—H35	118.0
C3—C4—C5	106.88 (15)	C34—C35—H35	118.0
C3—C4—H4	126.6	C33—O31—C36	116.89 (15)
C5—C4—H4	126.6	O31—C36—H36A	109.5
N1—C5—C6	125.70 (15)	O31—C36—H36B	109.5
N1—C5—C4	110.12 (14)	H36A—C36—H36B	109.5
C6—C5—C4	124.16 (15)	O31—C36—H36C	109.5
C5—C6—C7	122.52 (15)	H36A—C36—H36C	109.5
C5—C6—C11	119.09 (14)	H36B—C36—H36C	109.5
C7—C6—C11	118.39 (14)	Cl1^ii—Cl1—O2^ii	97.2 (6)
N2—C7—C6	126.14 (14)	Cl1^ii—Cl1—O4^ii	83.1 (6)
N2—C7—C8	109.61 (14)	O2^ii—Cl1—O4^ii	128.9 (2)
C6—C7—C8	124.24 (15)	Cl1^ii—Cl1—O2	61.2 (6)
C9—C8—C7	107.24 (14)	O2^ii—Cl1—O2	127.7 (7)
C9—C8—H8	126.4	O4^ii—Cl1—O2	21.9 (6)
C7—C8—H8	126.4	Cl1^ii—Cl1—O4	75.4 (6)
C8—C9—C10	107.31 (14)	O2^ii—Cl1—O4	21.8 (6)
C8—C9—H9	126.3	O4^ii—Cl1—O4	123.9 (7)
C10—C9—H9	126.3	O2—Cl1—O4	114.0 (4)
N2—C10—C1^i	126.50 (15)	Cl1^ii—Cl1—O3	166.6 (5)
N2—C10—C9	109.82 (14)	O2^ii—Cl1—O3	86.4 (4)
C1^i—C10—C9	123.66 (15)	O4^ii—Cl1—O3	84.7 (4)
C16—C11—C12	118.74 (15)	O2—Cl1—O3	106.5 (4)
C16—C11—C6	120.59 (15)	O4—Cl1—O3	107.4 (4)
C12—C11—C6	120.65 (15)	Cl1^ii—Cl1—O1	79.73 (4)
C13—C12—C11	120.16 (17)	O2^ii—Cl1—O1	116.1 (5)
C13—C12—H12	119.9	O4^ii—Cl1—O1	114.1 (4)
C11—C12—H12	119.9	O2—Cl1—O1	106.5 (4)
C14—C13—C12	120.68 (17)	O4—Cl1—O1	112.0 (4)
C14—C13—H13	119.7	O3—Cl1—O1	110.32 (17)
C12—C13—H13	119.7	Cl1^ii—Cl1—O3^ii	9.8 (3)
C15—C14—C13	119.41 (16)	O2^ii—Cl1—O3^ii	88.3 (4)
C15—C14—H14	120.3	O4^ii—Cl1—O3^ii	85.6 (4)
C13—C14—H14	120.3	O2—Cl1—O3^ii	64.1 (4)
C14—C15—C16	120.43 (17)	O4—Cl1—O3^ii	66.4 (4)
C14—C15—H15	119.8	O3—Cl1—O3^ii	162.2 (3)
C16—C15—H15	119.8	O1—Cl1—O3^ii	87.28 (13)
C15—C16—C11	120.57 (16)	Cl1—O1—Cl1^ii	20.54 (8)
C15—C16—H16	119.7	O4^ii—O2—Cl1^ii	97.4 (13)
C11—C16—H16	119.7	O4^ii—O2—Cl1	75.8 (13)
C18—C17—C22	118.85 (16)	Cl1^ii—O2—Cl1	21.61 (13)
C18—C17—C1	120.18 (16)	Cl1—O3—Cl1^ii	3.54 (12)
C22—C17—C1	120.96 (16)	O2^ii—O4—Cl1^ii	82.2 (13)
C17—C18—C19	120.50 (19)	O2^ii—O4—Cl1	60.7 (12)
C17—C18—H18	119.8	Cl1^ii—O4—Cl1	21.53 (14)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C35—H35···O4^ii	0.95	2.55	3.103 (8)	117
C36—H36C···O1	0.98	2.64	3.551 (3)	154

Symmetry code: (ii) −x+1, y, −z+1/2.