A 1:1 adduct of 3-(piperidin-1-yl)propionic acid with triphenyl­tin chloride

3-(Piperidin-1-yl)propionic acid forms a 1:1 adduct with chloro­triphenyl­tin, viz. chloro­triphen­yl[3-(piperidinium-1-yl)propionato]tin(IV) chloro­form solvate, [Sn(C₆H₅)₃(C₈H₁₅O₂)Cl]·CHCl₃. The acidic H atom is transferred to the piperidine N atom and an N—H...O intra­molecular hydrogen bond is formed.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.013 Å
• H-atom completeness 97%
• Disorder in solvent or counterion
• R factor = 0.045
• wR factor = 0.126
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      24.00 Deg.

Author Response: The data was collected several years ago and we have no chance of collecting more extensive data as the chemist who prepared the compounds is now retired. The structure is however half of the story begun in the previous paper, Part 1.

Alert level B
THETM01_ALERT_3_B  The value of sine(theta_max)/wavelength is less than 0.575
            Calculated sin(theta_max)/wavelength =    0.5723
PLAT023_ALERT_3_B Resolution (too) Low [sin(th)/Lambda < 0.6].....      24.00 Deg.
PLAT327_ALERT_2_B Check for Possibly Missing H on sp3? Carbon ....      >C100

Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT202_ALERT_3_C Isotropic non-H Atoms in Anion/Solvent .........          4
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.95 Ratio
PLAT221_ALERT_4_C Large Solvent/Anion Cl     Ueq(max)/Ueq(min) ...       3.64 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C5
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C24
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C33
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C31
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for       Cl21
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for       Cl22
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for       Cl31
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for       Cl33
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for       Cl23
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for       C200
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for       C300
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      33.00 Perc.
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         13
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl13   ..  O1      ..       3.19 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  C33    ..  Cl22    ..       3.17 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C26 H30 Cl N O2 Sn

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:C27 H31 Cl4 N1 O2 Sn1
            Atom count from the _atom_site data:  C27 H30 Cl4 N1 O2 Sn1
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    4
           From the CIF: _chemical_formula_sum  C27 H31 Cl4 N O2 Sn
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C        108.00    108.00    0.00
           H        124.00    120.00    4.00
           Cl        16.00     16.00    0.00
           N          4.00      4.00    0.00
           O          8.00      8.00    0.00
           Sn         4.00      4.00    0.00

   1 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
  24 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

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

---

Computing details

Data collection: XSCANS (Siemens, 1995); cell refinement: XSCANS; data reduction: SHELXTL (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

chlorotriphenyl[3-(piperidinium-1-yl)propionato]tin(V) chloroform solvate

Crystal data

[Sn(C6H5)3(C8H15O2)Cl]·CHCl3	F(000) = 1336
Mr = 662.02	Dx = 1.494 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 44 reflections
a = 12.7022 (8) Å	θ = 3.0–15.1°
b = 11.705 (1) Å	µ = 1.26 mm^−1
c = 20.493 (1) Å	T = 297 K
β = 105.049 (3)°	Cuboid, colourless
V = 2942.5 (4) Å^3	0.4 × 0.4 × 0.3 mm
Z = 4

Data collection

Siemens P4 diffractometer	3388 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
Graphite monochromator	θmax = 24.0°, θmin = 2.0°
2θ/ω scans	h = −1→14
Absorption correction: ψ scan (North et al., 1968)	k = −1→13
Tmin = 0.630, Tmax = 0.686	l = −23→23
5861 measured reflections	3 standard reflections every 97 reflections
4597 independent reflections	intensity decay: 8.0%

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ^2(Fo^2) + (0.06P)^2 + 6P] where P = (Fo^2 + 2Fc^2)/3
4597 reflections	(Δ/σ)max = 0.001
332 parameters	Δρmax = 0.67 e Å^−3
10 restraints	Δρmin = −0.80 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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)
Sn1	0.74589 (3)	1.07133 (3)	−0.191165 (19)	0.04988 (15)
Cl1	0.80681 (16)	1.08642 (17)	−0.30010 (9)	0.0826 (5)
O1	0.5336 (4)	1.0527 (4)	−0.0619 (2)	0.0745 (13)
O2	0.6801 (3)	1.0534 (4)	−0.09987 (19)	0.0625 (11)
N1	0.3825 (5)	0.8930 (5)	−0.1057 (3)	0.0705 (16)
H1N	0.412 (5)	0.962 (3)	−0.085 (3)	0.085*
C2	0.3290 (6)	0.9164 (7)	−0.1787 (3)	0.083 (2)
H2A	0.3817	0.9496	−0.2000	0.100*
H2B	0.3033	0.8453	−0.2016	0.100*
C3	0.2361 (7)	0.9959 (9)	−0.1852 (4)	0.107 (3)
H3A	0.2012	1.0076	−0.2327	0.129*
H3B	0.2636	1.0692	−0.1660	0.129*
C4	0.1515 (7)	0.9534 (10)	−0.1504 (5)	0.126 (4)
H4A	0.0962	1.0114	−0.1525	0.152*
H4B	0.1164	0.8852	−0.1727	0.152*
C5	0.2084 (7)	0.9272 (11)	−0.0775 (5)	0.131 (4)
H5A	0.1564	0.8950	−0.0554	0.157*
H5B	0.2364	0.9975	−0.0544	0.157*
C6	0.3009 (7)	0.8445 (8)	−0.0723 (4)	0.102 (3)
H6A	0.3357	0.8291	−0.0251	0.122*
H6B	0.2729	0.7729	−0.0938	0.122*
C11	0.4819 (6)	0.8235 (6)	−0.0956 (4)	0.079 (2)
H11A	0.4645	0.7536	−0.1216	0.095*
H11B	0.5069	0.8026	−0.0483	0.095*
C12	0.5733 (6)	0.8850 (5)	−0.1166 (3)	0.0680 (17)
H12A	0.6395	0.8404	−0.1013	0.082*
H12B	0.5555	0.8873	−0.1656	0.082*
C13	0.5963 (5)	1.0050 (5)	−0.0904 (3)	0.0544 (14)
C21	0.8359 (5)	0.9171 (5)	−0.1628 (4)	0.0629 (16)
C22	0.8780 (6)	0.8937 (7)	−0.0947 (5)	0.091 (2)
H22A	0.8623	0.9425	−0.0627	0.109*
C23	0.9429 (8)	0.7990 (11)	−0.0737 (7)	0.133 (5)
H23A	0.9709	0.7848	−0.0278	0.159*
C24	0.9656 (9)	0.7284 (10)	−0.1188 (9)	0.144 (6)
H24A	1.0112	0.6663	−0.1039	0.173*
C25	0.9230 (7)	0.7449 (8)	−0.1869 (8)	0.125 (4)
H25A	0.9367	0.6927	−0.2179	0.150*
C26	0.8590 (6)	0.8408 (6)	−0.2088 (5)	0.089 (2)
H26A	0.8314	0.8538	−0.2548	0.107*
C31	0.8224 (5)	1.2261 (5)	−0.1474 (3)	0.0598 (15)
C32	0.8972 (6)	1.2808 (7)	−0.1740 (4)	0.096 (3)
H32A	0.9150	1.2514	−0.2119	0.115*
C33	0.9465 (9)	1.3810 (9)	−0.1439 (6)	0.131 (4)
H33A	0.9980	1.4174	−0.1616	0.158*
C34	0.9208 (10)	1.4257 (8)	−0.0896 (6)	0.123 (4)
H34A	0.9534	1.4933	−0.0706	0.147*
C35	0.8490 (9)	1.3734 (7)	−0.0632 (5)	0.108 (3)
H35A	0.8330	1.4040	−0.0250	0.129*
C36	0.7974 (6)	1.2741 (6)	−0.0914 (4)	0.083 (2)
H36A	0.7460	1.2395	−0.0727	0.100*
C41	0.5791 (4)	1.0819 (5)	−0.2478 (3)	0.0491 (13)
C42	0.5348 (5)	1.0083 (6)	−0.3001 (3)	0.0664 (17)
H42A	0.5785	0.9531	−0.3125	0.080*
C43	0.4253 (6)	1.0155 (8)	−0.3344 (3)	0.087 (2)
H43A	0.3956	0.9638	−0.3687	0.104*
C44	0.3612 (6)	1.0986 (7)	−0.3179 (4)	0.081 (2)
H44A	0.2886	1.1053	−0.3420	0.097*
C45	0.4033 (5)	1.1709 (6)	−0.2666 (4)	0.0734 (19)
H45A	0.3589	1.2263	−0.2550	0.088*
C46	0.5114 (5)	1.1641 (5)	−0.2310 (3)	0.0573 (15)
H46A	0.5391	1.2145	−0.1957	0.069*
C100	0.2990 (9)	0.3822 (7)	−0.0733 (8)	0.166 (12)*	0.60
Cl11	0.3660 (7)	0.5002 (7)	−0.0260 (4)	0.187 (3)*	0.60
Cl12	0.2187 (7)	0.3225 (8)	−0.0229 (4)	0.200 (4)*	0.60
Cl13	0.4038 (4)	0.2890 (5)	−0.0832 (3)	0.109 (2)*	0.60
C200	0.2662 (11)	0.3539 (13)	−0.0809 (8)	0.060 (8)*	0.20
Cl21	0.3083 (12)	0.4017 (12)	0.0040 (6)	0.115 (4)*	0.20
Cl22	0.1675 (12)	0.2442 (13)	−0.0891 (8)	0.137 (5)*	0.20
Cl23	0.3734 (13)	0.2652 (9)	−0.0918 (6)	0.055 (2)*	0.20
C300	0.3121 (14)	0.4008 (15)	−0.0627 (9)	0.058 (10)*	0.20
Cl31	0.4275 (14)	0.4788 (16)	−0.0172 (9)	0.140 (5)*	0.20
Cl32	0.2411 (11)	0.3544 (11)	−0.0037 (6)	0.084 (3)*	0.20
Cl33	0.3363 (15)	0.2721 (16)	−0.1020 (9)	0.130 (8)*	0.20

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.0435 (2)	0.0548 (2)	0.0524 (2)	0.0000 (2)	0.01444 (16)	0.0023 (2)
Cl1	0.0876 (12)	0.0993 (14)	0.0734 (11)	−0.0106 (11)	0.0436 (9)	0.0022 (10)
O1	0.074 (3)	0.078 (3)	0.083 (3)	−0.025 (2)	0.043 (3)	−0.029 (2)
O2	0.050 (2)	0.087 (3)	0.053 (2)	−0.009 (2)	0.0186 (19)	−0.003 (2)
N1	0.077 (4)	0.079 (4)	0.060 (3)	−0.039 (3)	0.026 (3)	−0.013 (3)
C2	0.084 (5)	0.107 (6)	0.060 (4)	−0.028 (5)	0.024 (4)	0.004 (4)
C3	0.074 (6)	0.136 (8)	0.107 (7)	−0.030 (6)	0.014 (5)	0.021 (6)
C4	0.062 (5)	0.208 (12)	0.107 (7)	−0.041 (6)	0.016 (5)	−0.006 (7)
C5	0.071 (5)	0.233 (13)	0.098 (6)	−0.063 (7)	0.038 (5)	−0.040 (7)
C6	0.108 (6)	0.141 (8)	0.057 (4)	−0.077 (6)	0.022 (4)	−0.008 (5)
C11	0.110 (6)	0.059 (4)	0.073 (4)	−0.014 (4)	0.029 (4)	0.005 (3)
C12	0.082 (5)	0.059 (4)	0.066 (4)	0.001 (3)	0.023 (4)	0.001 (3)
C13	0.056 (4)	0.067 (4)	0.040 (3)	0.000 (3)	0.013 (3)	0.003 (3)
C21	0.044 (3)	0.055 (4)	0.095 (5)	0.001 (3)	0.026 (3)	0.014 (4)
C22	0.062 (4)	0.103 (6)	0.112 (6)	0.020 (4)	0.032 (4)	0.047 (5)
C23	0.077 (6)	0.144 (10)	0.189 (12)	0.029 (7)	0.057 (7)	0.090 (9)
C24	0.068 (6)	0.083 (7)	0.29 (2)	0.013 (6)	0.053 (9)	0.062 (10)
C25	0.067 (6)	0.062 (6)	0.256 (15)	−0.008 (5)	0.059 (7)	−0.031 (7)
C26	0.057 (4)	0.059 (4)	0.155 (8)	−0.006 (4)	0.034 (5)	−0.014 (5)
C31	0.053 (3)	0.055 (4)	0.063 (4)	−0.001 (3)	0.000 (3)	0.007 (3)
C32	0.086 (5)	0.098 (6)	0.099 (6)	−0.042 (5)	0.013 (4)	−0.004 (5)
C33	0.138 (9)	0.118 (8)	0.124 (8)	−0.070 (7)	0.010 (7)	0.022 (7)
C34	0.161 (10)	0.065 (5)	0.109 (8)	−0.039 (6)	−0.025 (7)	0.011 (5)
C35	0.133 (8)	0.065 (5)	0.102 (6)	0.006 (6)	−0.012 (6)	−0.014 (5)
C36	0.092 (5)	0.068 (4)	0.082 (5)	−0.001 (4)	0.009 (4)	−0.013 (4)
C41	0.045 (3)	0.057 (3)	0.046 (3)	−0.005 (3)	0.011 (2)	0.008 (3)
C42	0.063 (4)	0.076 (4)	0.057 (4)	−0.001 (3)	0.010 (3)	−0.006 (3)
C43	0.083 (5)	0.108 (6)	0.055 (4)	−0.018 (5)	−0.008 (4)	−0.009 (4)
C44	0.053 (4)	0.117 (7)	0.065 (4)	−0.003 (4)	0.001 (3)	0.027 (4)
C45	0.052 (4)	0.087 (5)	0.081 (5)	0.018 (4)	0.018 (3)	0.026 (4)
C46	0.059 (4)	0.057 (4)	0.056 (3)	0.002 (3)	0.017 (3)	0.007 (3)

Geometric parameters (Å, º)

Sn1—C21	2.135 (6)	C200—Cl22	1.772 (5)
Sn1—C41	2.138 (5)	C200—Cl21	1.772 (5)
Sn1—C31	2.139 (6)	C200—Cl23	1.772 (5)
Sn1—O2	2.248 (4)	C300—Cl32	1.772 (5)
Sn1—Cl1	2.5517 (16)	C300—Cl33	1.772 (5)
O1—C13	1.236 (7)	C300—Cl31	1.773 (5)
O2—C13	1.264 (7)	N1—H1N	0.94 (5)
N1—C11	1.470 (9)	C2—H2B	0.969
N1—C6	1.495 (8)	C2—H2A	0.970
N1—C2	1.499 (8)	C3—H3A	0.969
C2—C3	1.482 (12)	C3—H3B	0.970
C3—C4	1.519 (11)	C4—H4B	0.969
C4—C5	1.511 (12)	C4—H4A	0.970
C5—C6	1.505 (13)	C5—H5A	0.969
C11—C12	1.520 (9)	C5—H5B	0.970
C12—C13	1.505 (9)	C6—H6A	0.970
C21—C26	1.383 (10)	C6—H6B	0.970
C21—C22	1.386 (10)	C11—H11B	0.970
C22—C23	1.382 (12)	C11—H11A	0.970
C23—C24	1.325 (16)	C12—H12A	0.970
C24—C25	1.373 (16)	C12—H12B	0.971
C25—C26	1.390 (12)	C22—H22A	0.930
C31—C32	1.370 (9)	C23—H23A	0.930
C31—C36	1.388 (9)	C24—H24A	0.930
C32—C33	1.395 (12)	C25—H25A	0.930
C33—C34	1.343 (15)	C26—H26A	0.929
C34—C35	1.325 (14)	C32—H32A	0.930
C35—C36	1.385 (10)	C33—H33A	0.930
C41—C42	1.376 (8)	C34—H34A	0.930
C41—C46	1.392 (8)	C35—H35A	0.930
C42—C43	1.389 (9)	C36—H36A	0.931
C43—C44	1.366 (11)	C42—H42A	0.929
C44—C45	1.347 (10)	C43—H43A	0.930
C45—C46	1.379 (8)	C44—H44A	0.930
C100—Cl12	1.772 (5)	C45—H45A	0.930
C100—Cl13	1.773 (5)	C46—H46A	0.929
C100—Cl11	1.773 (5)
C21—Sn1—C41	125.6 (2)	H2A—C2—C3	109.54
C21—Sn1—C31	116.7 (2)	H2A—C2—N1	109.59
C41—Sn1—C31	117.2 (2)	H3A—C3—H3B	107.76
C21—Sn1—O2	89.0 (2)	H3A—C3—C2	108.97
C41—Sn1—O2	85.83 (17)	H3A—C3—C4	108.84
C31—Sn1—O2	87.5 (2)	H3B—C3—C2	108.93
C21—Sn1—Cl1	91.93 (19)	H3B—C3—C4	108.85
C41—Sn1—Cl1	90.22 (15)	H4B—C4—H4A	108.45
C31—Sn1—Cl1	95.73 (18)	H4B—C4—C5	110.01
O2—Sn1—Cl1	175.73 (11)	H4B—C4—C3	110.07
C13—O2—Sn1	132.8 (4)	H4A—C4—C5	109.92
C11—N1—C6	113.4 (6)	H4A—C4—C3	110.02
C11—N1—C2	113.0 (6)	H5A—C5—H5B	108.06
C6—N1—C2	109.7 (5)	H5A—C5—C6	109.34
C3—C2—N1	110.4 (6)	H5A—C5—C4	109.37
C2—C3—C4	113.4 (8)	H5B—C5—C6	109.31
C5—C4—C3	108.4 (7)	H5B—C5—C4	109.32
C4—C5—C6	111.5 (8)	H6A—C6—H6B	108.09
N1—C6—C5	110.1 (7)	H6A—C6—N1	109.67
N1—C11—C12	112.9 (5)	H6A—C6—C5	109.60
C13—C12—C11	115.7 (6)	H6B—C6—N1	109.64
O1—C13—O2	122.8 (6)	H6B—C6—C5	109.64
O1—C13—C12	120.0 (6)	H11B—C11—H11A	107.76
O2—C13—C12	117.2 (5)	H11B—C11—N1	109.06
C26—C21—C22	117.6 (7)	H11B—C11—C12	109.06
C26—C21—Sn1	123.6 (6)	H11A—C11—N1	108.93
C22—C21—Sn1	118.7 (5)	H11A—C11—C12	109.01
C23—C22—C21	121.0 (10)	H12A—C12—H12B	107.39
C24—C23—C22	120.2 (12)	H12A—C12—C13	108.38
C23—C24—C25	121.4 (11)	H12A—C12—C11	108.38
C24—C25—C26	119.0 (11)	H12B—C12—C13	108.34
C21—C26—C25	120.7 (10)	H12B—C12—C11	108.43
C32—C31—C36	118.0 (7)	H22A—C22—C23	119.55
C32—C31—Sn1	121.1 (5)	H22A—C22—C21	119.44
C36—C31—Sn1	120.9 (5)	H23A—C23—C24	119.88
C31—C32—C33	119.8 (9)	H23A—C23—C22	119.92
C34—C33—C32	121.0 (10)	H24A—C24—C23	119.19
C35—C34—C33	120.0 (9)	H24A—C24—C25	119.41
C34—C35—C36	121.3 (10)	H25A—C25—C24	120.51
C35—C36—C31	120.0 (8)	H25A—C25—C26	120.50
C42—C41—C46	118.1 (5)	H26A—C26—C21	119.64
C42—C41—Sn1	122.3 (4)	H26A—C26—C25	119.65
C46—C41—Sn1	119.6 (4)	H32A—C32—C31	120.23
C41—C42—C43	120.7 (7)	H32A—C32—C33	120.13
C44—C43—C42	120.0 (7)	H33A—C33—C34	119.43
C45—C44—C43	120.0 (6)	H33A—C33—C32	119.55
C44—C45—C46	121.0 (7)	H34A—C34—C35	120.06
C45—C46—C41	120.2 (6)	H34A—C34—C33	120.01
Cl12—C100—Cl13	112.8 (7)	H35A—C35—C34	119.32
Cl12—C100—Cl11	104.8 (7)	H35A—C35—C36	119.43
Cl13—C100—Cl11	105.9 (7)	H36A—C36—C35	119.98
Cl22—C200—Cl21	110.4 (11)	H36A—C36—C31	120.01
Cl22—C200—Cl23	96.4 (10)	H42A—C42—C41	119.72
Cl21—C200—Cl23	105.3 (9)	H42A—C42—C43	119.65
Cl32—C300—Cl33	103.2 (10)	H43A—C43—C44	119.97
Cl32—C300—Cl31	107.3 (12)	H43A—C43—C42	119.97
Cl33—C300—Cl31	117.4 (14)	H44A—C44—C45	119.97
H1N—N1—C11	101 (4)	H44A—C44—C43	120.09
H1N—N1—C6	111 (4)	H45A—C45—C44	119.56
H1N—N1—C2	109 (3)	H45A—C45—C46	119.43
H2B—C2—H2A	108.12	H46A—C46—C45	119.92
H2B—C2—C3	109.60	H46A—C46—C41	119.88
H2B—C2—N1	109.55

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.94 (5)	1.83 (6)	2.663 (8)	145 (5)