Crystal structure of (3E,5E)-3,5-bis­[4-(di­ethyl­aza­nium­yl)benzyl­idene]-1-methyl-4-oxopiperidin-1-ium trichloride dihydrate: a potential biophotonic material

A stable oxopiperidinium trication salt was synthesized. In the crystal, N—H...Cl, C—H...Cl and C—H...O hydrogen bonds link cations and anions into a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.004 Å
• H-atom completeness 91%
• Disorder in solvent or counterion
• R factor = 0.058
• wR factor = 0.164
• Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT306_ALERT_2_B Isolated Oxygen Atom (H-atoms Missing ?) .......        O1A Check
PLAT306_ALERT_2_B Isolated Oxygen Atom (H-atoms Missing ?) .......        O2A Check
PLAT430_ALERT_2_B Short Inter D...A Contact  O1A    ..  O2A     ..       2.77 Ang.

Alert level C
PLAT041_ALERT_1_C Calc. and Reported SumFormula    Strings  Differ     Please Check
PLAT043_ALERT_1_C Calculated and Reported Mol. Weight Differ by ..       4.03 Check
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...     Please Check
PLAT222_ALERT_3_C Large Non-Solvent  H     Uiso(max)/Uiso(min) ...        5.5 Ratio
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0042 Ang.
PLAT430_ALERT_2_C Short Inter D...A Contact  O1A    ..  O1A     ..       2.85 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.357 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         43 Report
PLAT918_ALERT_3_C Reflection(s) with I(obs) much smaller I(calc) .          1 Check
PLAT975_ALERT_2_C Check Calcd Residual Density  1.02A From     O1A       0.51 eA-3
PLAT975_ALERT_2_C Check Calcd Residual Density  0.67A From     O1A       0.43 eA-3
PLAT976_ALERT_2_C Check Calcd Residual Density  0.47A From     O2A      -0.62 eA-3
PLAT976_ALERT_2_C Check Calcd Residual Density  0.58A From     O2A      -0.62 eA-3
PLAT976_ALERT_2_C Check Calcd Residual Density  0.62A From     O2A      -0.54 eA-3

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C28 H44 Cl3 N3 O3
            Atom count from the _atom_site data:  C28 H40 Cl3 N3 O3
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    2
           From the CIF: _chemical_formula_sum  C28 H44 Cl3 N3 O3
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         56.00     56.00    0.00
           H         88.00     80.00    8.00
           Cl         6.00      6.00    0.00
           N          6.00      6.00    0.00
           O          6.00      6.00    0.00
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          6 Note
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ..........    0.00100 Degree
PLAT302_ALERT_4_G Anion/Solvent Disorder ............ Percentage =         20 Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms (   0.89) in Resd. #          4 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms (   0.10) in Resd. #          5 Check
PLAT431_ALERT_2_G Short Inter HL..A  Contact Cl1    ..  O2A     ..       3.14 Ang.
PLAT432_ALERT_2_G Short Inter X...Y Contact  Cl3A   ..  C16     ..       3.24 Ang.
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          3 Note
              Cl
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          3 Note
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         18 Note

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

   8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  13 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

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(3E,5E)-3,5-Bis[4-(diethylazaniumyl)benzylidene]-1-methyl- 4-oxopiperidin-1-ium

Crystal data

C28H40N3O^3+·3Cl^−·2H2O	Z = 2
Mr = 577.01	F(000) = 616
Triclinic, P1	Dx = 1.290 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.0933 (5) Å	Cell parameters from 4567 reflections
b = 12.0661 (6) Å	θ = 2.5–26.0°
c = 13.7576 (6) Å	µ = 0.34 mm^−1
α = 97.759 (1)°	T = 100 K
β = 110.795 (1)°	Block, colourless
γ = 102.733 (1)°	0.18 × 0.12 × 0.10 mm
V = 1485.46 (12) Å^3

Data collection

Bruker APEXII CCD diffractometer	5787 independent reflections
Radiation source: fine-focus sealed tube	5056 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
φ and ω scans	θmax = 26.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −12→12
Tmin = 0.941, Tmax = 0.967	k = −14→14
11768 measured reflections	l = −16→16

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.091P)^2 + 1.9P] where P = (Fo^2 + 2Fc^2)/3
5787 reflections	(Δ/σ)max = 0.001
356 parameters	Δρmax = 1.13 e Å^−3
3 restraints	Δρmin = −0.62 e Å^−3

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.69912 (7)	0.36862 (6)	0.70014 (6)	0.0379 (2)
Cl2	1.10763 (7)	0.16702 (5)	0.19807 (5)	0.02863 (18)
Cl3	0.41255 (10)	0.74605 (6)	0.84491 (6)	0.0319 (3)	0.895 (4)
Cl3A	0.4816 (15)	0.7207 (9)	0.8555 (8)	0.059 (3)*	0.105 (4)
O1	0.2253 (2)	−0.04179 (15)	0.41664 (15)	0.0288 (4)
N1	0.4116 (2)	0.26939 (17)	0.37806 (17)	0.0229 (4)
H1D	0.3294 (19)	0.239 (2)	0.3181 (14)	0.017 (6)*
N2	0.8498 (2)	−0.06652 (19)	0.13943 (17)	0.0251 (5)
H2C	0.924 (3)	0.0015 (16)	0.165 (2)	0.034 (8)*
N3	0.1387 (3)	0.5404 (2)	0.78810 (19)	0.0308 (5)
H3A	0.221 (3)	0.602 (3)	0.809 (4)	0.093 (17)*
C1	0.4892 (4)	0.3863 (2)	0.3704 (3)	0.0365 (7)
H1A	0.4236	0.4366	0.3621	0.055*
H1B	0.5157	0.3772	0.3084	0.055*
H1C	0.5792	0.4220	0.4356	0.055*
C2	0.3736 (3)	0.2804 (2)	0.4734 (2)	0.0237 (5)
H2A	0.3144	0.3362	0.4704	0.028*
H2B	0.4656	0.3114	0.5392	0.028*
C3	0.2870 (3)	0.1637 (2)	0.47709 (18)	0.0204 (5)
C4	0.3029 (3)	0.0544 (2)	0.42288 (19)	0.0213 (5)
C5	0.4212 (3)	0.0674 (2)	0.37980 (18)	0.0204 (5)
C6	0.5053 (3)	0.1887 (2)	0.3839 (2)	0.0249 (5)
H6A	0.5953	0.2179	0.4513	0.030*
H6B	0.5368	0.1866	0.3235	0.030*
C7	0.4468 (3)	−0.0299 (2)	0.33955 (18)	0.0204 (5)
H7A	0.3874	−0.1019	0.3414	0.024*
C8	0.5559 (3)	−0.0379 (2)	0.29304 (19)	0.0223 (5)
C9	0.5226 (3)	−0.1372 (2)	0.2139 (2)	0.0261 (5)
H9A	0.4346	−0.1988	0.1951	0.031*
C10	0.6172 (3)	−0.1468 (2)	0.1624 (2)	0.0299 (6)
H10A	0.5930	−0.2134	0.1070	0.036*
C11	0.7474 (3)	−0.0574 (2)	0.1932 (2)	0.0255 (5)
C12	0.7871 (3)	0.0384 (2)	0.2743 (2)	0.0273 (5)
H12A	0.8786	0.0970	0.2960	0.033*
C13	0.6914 (3)	0.0482 (2)	0.3240 (2)	0.0274 (5)
H13A	0.7179	0.1145	0.3803	0.033*
C14	0.9212 (3)	−0.1619 (2)	0.1686 (2)	0.0294 (6)
H14A	0.9628	−0.1503	0.2474	0.035*
H14B	0.8442	−0.2384	0.1379	0.035*
C15	1.0423 (3)	−0.1647 (3)	0.1296 (2)	0.0335 (6)
H15A	1.0940	−0.2198	0.1599	0.050*
H15B	1.1127	−0.0865	0.1521	0.050*
H15C	0.9992	−0.1897	0.0514	0.050*
C16	0.7779 (3)	−0.0775 (3)	0.0204 (2)	0.0314 (6)
H16A	0.6993	−0.1530	−0.0129	0.038*
H16B	0.8528	−0.0778	−0.0104	0.038*
C17	0.7110 (3)	0.0207 (3)	−0.0065 (2)	0.0357 (6)
H17A	0.6672	0.0103	−0.0844	0.054*
H17B	0.7883	0.0957	0.0258	0.054*
H17C	0.6340	0.0196	0.0214	0.054*
C18	0.1975 (3)	0.1549 (2)	0.53023 (19)	0.0205 (5)
H18A	0.1401	0.0785	0.5243	0.025*
C19	0.1804 (3)	0.2522 (2)	0.59652 (19)	0.0203 (5)
C20	0.0408 (3)	0.2538 (2)	0.5932 (2)	0.0247 (5)
H20A	−0.0434	0.1902	0.5488	0.030*
C21	0.0235 (3)	0.3478 (3)	0.6542 (2)	0.0300 (6)
H21A	−0.0719	0.3494	0.6503	0.036*
C22	0.1474 (3)	0.4382 (2)	0.7200 (2)	0.0285 (6)
C23	0.2872 (3)	0.4361 (2)	0.7293 (2)	0.0276 (5)
H23A	0.3716	0.4972	0.7780	0.033*
C24	0.3036 (3)	0.3444 (2)	0.6671 (2)	0.0245 (5)
H24A	0.3998	0.3437	0.6723	0.029*
C25	0.1258 (3)	0.5097 (2)	0.8880 (2)	0.0312 (6)
H25A	0.1994	0.4683	0.9191	0.037*
H25B	0.0260	0.4562	0.8689	0.037*
C26	0.1511 (5)	0.6178 (3)	0.9711 (3)	0.0505 (9)
H26A	0.1669	0.5976	1.0402	0.076*
H26B	0.0643	0.6469	0.9486	0.076*
H26C	0.2385	0.6784	0.9779	0.076*
C27	0.0234 (3)	0.5949 (2)	0.7310 (2)	0.0336 (6)
H27A	0.0316	0.6662	0.7805	0.040*
H27B	−0.0757	0.5397	0.7110	0.040*
C28	0.0356 (4)	0.6268 (3)	0.6323 (2)	0.0416 (7)
H28A	−0.0141	0.6870	0.6145	0.062*
H28B	−0.0115	0.5574	0.5728	0.062*
H28C	0.1403	0.6569	0.6451	0.062*
O1A	0.5901 (3)	0.6022 (2)	0.9885 (3)	0.0693 (8)
O2A	0.7711 (5)	0.5914 (3)	0.8786 (3)	0.0984 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0277 (3)	0.0416 (4)	0.0486 (4)	0.0113 (3)	0.0192 (3)	0.0105 (3)
Cl2	0.0306 (3)	0.0305 (3)	0.0273 (3)	0.0124 (3)	0.0130 (3)	0.0049 (2)
Cl3	0.0304 (5)	0.0243 (4)	0.0365 (5)	0.0025 (3)	0.0142 (3)	−0.0012 (3)
O1	0.0339 (10)	0.0195 (9)	0.0368 (10)	0.0005 (7)	0.0247 (8)	0.0012 (7)
N1	0.0286 (11)	0.0174 (10)	0.0253 (11)	0.0029 (8)	0.0169 (9)	0.0023 (8)
N2	0.0276 (11)	0.0259 (11)	0.0264 (11)	0.0107 (9)	0.0140 (9)	0.0071 (9)
N3	0.0442 (14)	0.0291 (12)	0.0295 (12)	0.0167 (11)	0.0221 (11)	0.0090 (10)
C1	0.0512 (18)	0.0193 (12)	0.0517 (18)	0.0051 (12)	0.0380 (15)	0.0080 (12)
C2	0.0297 (13)	0.0205 (11)	0.0241 (12)	0.0045 (10)	0.0174 (10)	0.0016 (9)
C3	0.0209 (11)	0.0209 (11)	0.0190 (11)	0.0048 (9)	0.0089 (9)	0.0033 (9)
C4	0.0226 (11)	0.0223 (12)	0.0198 (11)	0.0040 (9)	0.0114 (10)	0.0029 (9)
C5	0.0200 (11)	0.0221 (11)	0.0202 (11)	0.0042 (9)	0.0109 (9)	0.0039 (9)
C6	0.0248 (12)	0.0208 (12)	0.0336 (13)	0.0047 (10)	0.0193 (11)	0.0020 (10)
C7	0.0213 (11)	0.0222 (11)	0.0190 (11)	0.0061 (9)	0.0091 (9)	0.0059 (9)
C8	0.0281 (12)	0.0247 (12)	0.0232 (12)	0.0141 (10)	0.0146 (10)	0.0114 (10)
C9	0.0306 (13)	0.0242 (12)	0.0304 (13)	0.0115 (10)	0.0168 (11)	0.0094 (10)
C10	0.0390 (15)	0.0258 (13)	0.0312 (14)	0.0159 (11)	0.0181 (12)	0.0049 (11)
C11	0.0277 (13)	0.0311 (13)	0.0272 (13)	0.0132 (11)	0.0160 (11)	0.0154 (11)
C12	0.0255 (12)	0.0276 (13)	0.0340 (14)	0.0094 (10)	0.0161 (11)	0.0090 (11)
C13	0.0268 (13)	0.0293 (13)	0.0314 (14)	0.0112 (11)	0.0156 (11)	0.0081 (11)
C14	0.0357 (14)	0.0277 (13)	0.0323 (14)	0.0166 (11)	0.0163 (12)	0.0106 (11)
C15	0.0347 (15)	0.0333 (14)	0.0391 (15)	0.0163 (12)	0.0185 (13)	0.0077 (12)
C16	0.0291 (13)	0.0477 (16)	0.0205 (13)	0.0132 (12)	0.0122 (11)	0.0078 (11)
C17	0.0347 (15)	0.0444 (16)	0.0331 (15)	0.0120 (13)	0.0170 (12)	0.0150 (13)
C18	0.0218 (11)	0.0189 (11)	0.0215 (11)	0.0045 (9)	0.0098 (9)	0.0052 (9)
C19	0.0261 (12)	0.0207 (11)	0.0208 (11)	0.0081 (9)	0.0147 (10)	0.0092 (9)
C20	0.0229 (12)	0.0305 (13)	0.0242 (12)	0.0071 (10)	0.0131 (10)	0.0087 (10)
C21	0.0350 (14)	0.0423 (15)	0.0314 (14)	0.0229 (12)	0.0241 (12)	0.0185 (12)
C22	0.0463 (16)	0.0261 (13)	0.0242 (12)	0.0179 (12)	0.0204 (12)	0.0115 (10)
C23	0.0367 (14)	0.0238 (12)	0.0247 (12)	0.0056 (11)	0.0170 (11)	0.0049 (10)
C24	0.0265 (12)	0.0253 (12)	0.0240 (12)	0.0051 (10)	0.0145 (10)	0.0050 (10)
C25	0.0481 (16)	0.0274 (13)	0.0302 (14)	0.0151 (12)	0.0256 (13)	0.0104 (11)
C26	0.093 (3)	0.0444 (18)	0.0347 (16)	0.0295 (19)	0.0425 (18)	0.0120 (14)
C27	0.0432 (16)	0.0266 (13)	0.0366 (15)	0.0180 (12)	0.0171 (13)	0.0087 (11)
C28	0.057 (2)	0.0377 (16)	0.0338 (16)	0.0221 (15)	0.0162 (14)	0.0130 (13)
O1A	0.0472 (14)	0.0392 (13)	0.104 (2)	0.0153 (11)	0.0153 (15)	−0.0023 (14)
O2A	0.142 (4)	0.075 (2)	0.076 (2)	0.027 (2)	0.044 (2)	0.0198 (18)

Geometric parameters (Å, º)

O1—C4	1.221 (3)	C13—H13A	0.9500
N1—C2	1.489 (3)	C14—C15	1.504 (4)
N1—C6	1.491 (3)	C14—H14A	0.9900
N1—C1	1.492 (3)	C14—H14B	0.9900
N1—H1D	0.895 (10)	C15—H15A	0.9800
N2—C11	1.483 (3)	C15—H15B	0.9800
N2—C16	1.510 (3)	C15—H15C	0.9800
N2—C14	1.513 (3)	C16—C17	1.513 (4)
N2—H2C	0.907 (10)	C16—H16A	0.9900
N3—C22	1.483 (3)	C16—H16B	0.9900
N3—C27	1.494 (4)	C17—H17A	0.9800
N3—C25	1.512 (3)	C17—H17B	0.9800
N3—H3A	0.912 (10)	C17—H17C	0.9800
C1—H1A	0.9800	C18—C19	1.468 (3)
C1—H1B	0.9800	C18—H18A	0.9500
C1—H1C	0.9800	C19—C20	1.398 (3)
C2—C3	1.503 (3)	C19—C24	1.402 (4)
C2—H2A	0.9900	C20—C21	1.399 (4)
C2—H2B	0.9900	C20—H20A	0.9500
C3—C18	1.345 (3)	C21—C22	1.379 (4)
C3—C4	1.495 (3)	C21—H21A	0.9500
C4—C5	1.499 (3)	C22—C23	1.377 (4)
C5—C7	1.346 (3)	C23—C24	1.382 (4)
C5—C6	1.503 (3)	C23—H23A	0.9500
C6—H6A	0.9900	C24—H24A	0.9500
C6—H6B	0.9900	C25—C26	1.521 (4)
C7—C8	1.470 (3)	C25—H25A	0.9900
C7—H7A	0.9500	C25—H25B	0.9900
C8—C9	1.394 (4)	C26—H26A	0.9800
C8—C13	1.404 (4)	C26—H26B	0.9800
C9—C10	1.391 (4)	C26—H26C	0.9800
C9—H9A	0.9500	C27—C28	1.499 (4)
C10—C11	1.388 (4)	C27—H27A	0.9900
C10—H10A	0.9500	C27—H27B	0.9900
C11—C12	1.367 (4)	C28—H28A	0.9800
C12—C13	1.383 (4)	C28—H28B	0.9800
C12—H12A	0.9500	C28—H28C	0.9800
C2—N1—C6	109.88 (19)	N2—C14—H14A	108.9
C2—N1—C1	110.58 (19)	C15—C14—H14B	108.9
C6—N1—C1	110.6 (2)	N2—C14—H14B	108.9
C2—N1—H1D	110.5 (18)	H14A—C14—H14B	107.7
C6—N1—H1D	107.7 (17)	C14—C15—H15A	109.5
C1—N1—H1D	107.5 (17)	C14—C15—H15B	109.5
C11—N2—C16	112.58 (19)	H15A—C15—H15B	109.5
C11—N2—C14	110.55 (19)	C14—C15—H15C	109.5
C16—N2—C14	113.6 (2)	H15A—C15—H15C	109.5
C11—N2—H2C	108 (2)	H15B—C15—H15C	109.5
C16—N2—H2C	105 (2)	N2—C16—C17	112.6 (2)
C14—N2—H2C	107 (2)	N2—C16—H16A	109.1
C22—N3—C27	114.4 (2)	C17—C16—H16A	109.1
C22—N3—C25	110.3 (2)	N2—C16—H16B	109.1
C27—N3—C25	112.8 (2)	C17—C16—H16B	109.1
C22—N3—H3A	112 (3)	H16A—C16—H16B	107.8
C27—N3—H3A	99 (3)	C16—C17—H17A	109.5
C25—N3—H3A	108 (3)	C16—C17—H17B	109.5
N1—C1—H1A	109.5	H17A—C17—H17B	109.5
N1—C1—H1B	109.5	C16—C17—H17C	109.5
H1A—C1—H1B	109.5	H17A—C17—H17C	109.5
N1—C1—H1C	109.5	H17B—C17—H17C	109.5
H1A—C1—H1C	109.5	C3—C18—C19	126.0 (2)
H1B—C1—H1C	109.5	C3—C18—H18A	117.0
N1—C2—C3	110.49 (19)	C19—C18—H18A	117.0
N1—C2—H2A	109.6	C20—C19—C24	118.1 (2)
C3—C2—H2A	109.6	C20—C19—C18	120.7 (2)
N1—C2—H2B	109.6	C24—C19—C18	121.1 (2)
C3—C2—H2B	109.6	C19—C20—C21	120.9 (2)
H2A—C2—H2B	108.1	C19—C20—H20A	119.5
C18—C3—C4	118.8 (2)	C21—C20—H20A	119.5
C18—C3—C2	121.6 (2)	C22—C21—C20	118.7 (2)
C4—C3—C2	119.6 (2)	C22—C21—H21A	120.6
O1—C4—C3	121.3 (2)	C20—C21—H21A	120.6
O1—C4—C5	121.4 (2)	C23—C22—C21	121.6 (2)
C3—C4—C5	117.3 (2)	C23—C22—N3	116.2 (2)
C7—C5—C4	118.3 (2)	C21—C22—N3	122.1 (2)
C7—C5—C6	123.4 (2)	C22—C23—C24	119.4 (3)
C4—C5—C6	118.2 (2)	C22—C23—H23A	120.3
N1—C6—C5	110.69 (19)	C24—C23—H23A	120.3
N1—C6—H6A	109.5	C23—C24—C19	121.0 (2)
C5—C6—H6A	109.5	C23—C24—H24A	119.5
N1—C6—H6B	109.5	C19—C24—H24A	119.5
C5—C6—H6B	109.5	N3—C25—C26	111.9 (2)
H6A—C6—H6B	108.1	N3—C25—H25A	109.2
C5—C7—C8	127.6 (2)	C26—C25—H25A	109.2
C5—C7—H7A	116.2	N3—C25—H25B	109.2
C8—C7—H7A	116.2	C26—C25—H25B	109.2
C9—C8—C13	118.3 (2)	H25A—C25—H25B	107.9
C9—C8—C7	117.8 (2)	C25—C26—H26A	109.5
C13—C8—C7	123.8 (2)	C25—C26—H26B	109.5
C10—C9—C8	120.6 (2)	H26A—C26—H26B	109.5
C10—C9—H9A	119.7	C25—C26—H26C	109.5
C8—C9—H9A	119.7	H26A—C26—H26C	109.5
C11—C10—C9	118.9 (2)	H26B—C26—H26C	109.5
C11—C10—H10A	120.6	N3—C27—C28	113.5 (2)
C9—C10—H10A	120.6	N3—C27—H27A	108.9
C12—C11—C10	122.0 (2)	C28—C27—H27A	108.9
C12—C11—N2	118.4 (2)	N3—C27—H27B	108.9
C10—C11—N2	119.6 (2)	C28—C27—H27B	108.9
C11—C12—C13	118.7 (2)	H27A—C27—H27B	107.7
C11—C12—H12A	120.6	C27—C28—H28A	109.5
C13—C12—H12A	120.6	C27—C28—H28B	109.5
C12—C13—C8	121.3 (2)	H28A—C28—H28B	109.5
C12—C13—H13A	119.3	C27—C28—H28C	109.5
C8—C13—H13A	119.3	H28A—C28—H28C	109.5
C15—C14—N2	113.3 (2)	H28B—C28—H28C	109.5
C15—C14—H14A	108.9

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2C···Cl2	0.91 (1)	2.27 (1)	3.166 (2)	169 (3)
N3—H3A···Cl3	0.91 (1)	2.14 (1)	3.054 (3)	175 (5)
N1—H1D···Cl2^i	0.90 (1)	2.15 (1)	3.030 (2)	167 (2)
C1—H1B···Cl3^ii	0.98	2.81	3.717 (4)	154
C2—H2B···Cl1	0.99	2.47	3.456 (3)	174
C6—H6B···Cl3^ii	0.99	2.73	3.668 (3)	158
C10—H10A···O1A^iii	0.95	2.56	3.491 (4)	166
C16—H16A···Cl3^iii	0.99	2.73	3.576 (3)	143
C20—H20A···O1^iv	0.95	2.49	3.224 (3)	134
C21—H21A···Cl1^i	0.95	2.68	3.602 (3)	164
C25—H25A···O1A^v	0.99	2.45	3.435 (4)	171
C27—H27A···Cl2^ii	0.99	2.74	3.576 (3)	143
C27—H27B···Cl1^i	0.99	2.66	3.621 (3)	164

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