Solvent inclusion in the crystal structure of bis­[(adamantan-1-yl)methanaminium chloride] 1,4-dioxane hemisolvate monohydrate explained using the computed crystal energy landscape

Energy computations on the title salt show a clear preference for solvated structures, which correlates with the most effective formation of hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.056
• wR factor = 0.105
• Data-to-parameter ratio = 20.8

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      8.463 Check

Alert level G
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.003 Degree
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          5 Note
              Cl
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         34 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density          12 Note

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

   2 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
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker 2015); cell refinement: SAINT (Bruker 2015); data reduction: SAINT (Bruker 2015); program(s) used to solve structure: XT (Sheldrick, 2015); program(s) used to refine structure: SHELXL (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Bis[(adamantan-1-yl)methanaminium chloride] 1,4-dioxane hemisolvate monohydrate

Crystal data

2C11H20N^+·2Cl^−·0.5C4H8O2·H2O	Z = 2
Mr = 465.53	F(000) = 508
Triclinic, P1	Dx = 1.229 Mg m^−3
a = 6.4941 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.491 (2) Å	Cell parameters from 4531 reflections
c = 15.086 (3) Å	θ = 2.3–28.0°
α = 102.911 (3)°	µ = 0.28 mm^−1
β = 91.824 (3)°	T = 100 K
γ = 101.500 (3)°	Needle, clear light colourless
V = 1258.5 (4) Å^3	0.2 × 0.05 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer	4285 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.096
Absorption correction: multi-scan (SADABS; Bruker, 2015)	θmax = 28.4°, θmin = 1.6°
Tmin = 0.655, Tmax = 0.746	h = −8→8
35014 measured reflections	k = −18→17
6312 independent reflections	l = −20→20

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.105	w = 1/[σ^2(Fo^2) + (0.0415P)^2 + 0.1332P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
6312 reflections	Δρmax = 0.49 e Å^−3
303 parameters	Δρmin = −0.39 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
Cl1	0.87597 (8)	0.25420 (4)	0.41712 (4)	0.02117 (14)
O1	0.7543 (3)	0.01392 (17)	0.29766 (13)	0.0350 (4)
H1D	0.744 (5)	−0.019 (3)	0.337 (2)	0.067 (12)*
H1E	0.789 (5)	0.081 (3)	0.331 (2)	0.069 (11)*
N1	0.3859 (3)	0.22378 (16)	0.37519 (13)	0.0184 (4)
H1A	0.347 (4)	0.202 (2)	0.4221 (18)	0.034 (7)*
H1B	0.331 (4)	0.280 (2)	0.3786 (16)	0.032 (7)*
H1C	0.540 (5)	0.242 (2)	0.3820 (18)	0.049 (8)*
C1	0.3307 (3)	0.17360 (15)	0.20310 (13)	0.0124 (4)
C2	0.1981 (3)	0.25504 (15)	0.19496 (14)	0.0149 (4)
H2A	0.0482	0.2266	0.2017	0.018*
H2B	0.2472	0.3185	0.2443	0.018*
C3	0.2196 (3)	0.28259 (15)	0.10183 (14)	0.0150 (4)
H3	0.1337	0.3354	0.0972	0.018*
C4	0.4520 (3)	0.32784 (16)	0.09241 (14)	0.0161 (4)
H4A	0.4666	0.3470	0.0329	0.019*
H4B	0.5031	0.3914	0.1414	0.019*
C5	0.5838 (3)	0.24691 (15)	0.09893 (13)	0.0141 (4)
H5	0.7351	0.2763	0.0925	0.017*
C6	0.5625 (3)	0.21869 (16)	0.19195 (13)	0.0131 (4)
H6A	0.6486	0.1669	0.1966	0.016*
H6B	0.6157	0.2816	0.2414	0.016*
C7	0.5040 (3)	0.14874 (16)	0.02254 (14)	0.0172 (4)
H7A	0.5184	0.1662	−0.0376	0.021*
H7B	0.5894	0.0964	0.0261	0.021*
C8	0.2722 (3)	0.10384 (16)	0.03253 (14)	0.0160 (4)
H8	0.2205	0.0399	−0.0172	0.019*
C9	0.1409 (3)	0.18475 (16)	0.02568 (14)	0.0174 (4)
H9A	0.1532	0.2025	−0.0344	0.021*
H9B	−0.0094	0.1558	0.0312	0.021*
C10	0.2512 (3)	0.07589 (15)	0.12521 (13)	0.0153 (4)
H10A	0.3343	0.0228	0.1293	0.018*
H10B	0.1017	0.0461	0.1314	0.018*
C11	0.3041 (3)	0.13900 (16)	0.29224 (13)	0.0166 (4)
H11A	0.1525	0.1115	0.2965	0.020*
H11B	0.3785	0.0815	0.2912	0.020*
Cl2	1.31606 (7)	0.11138 (4)	0.53791 (3)	0.01540 (12)
O2	0.4015 (2)	0.44325 (11)	0.41377 (10)	0.0234 (4)
C23	0.2855 (3)	0.49326 (18)	0.48258 (16)	0.0282 (6)
H23A	0.1386	0.4529	0.4765	0.034*
H23B	0.2817	0.5637	0.4744	0.034*
C24	0.6155 (4)	0.49844 (19)	0.42468 (16)	0.0307 (6)
H24A	0.6217	0.5691	0.4150	0.037*
H24B	0.6960	0.4621	0.3781	0.037*
N2	0.8388 (3)	0.12390 (16)	0.56887 (12)	0.0161 (4)
H2C	0.785 (4)	0.062 (2)	0.5387 (16)	0.022 (6)*
H2D	0.788 (4)	0.165 (2)	0.5421 (17)	0.031 (7)*
H2E	0.977 (4)	0.1327 (19)	0.5613 (16)	0.033 (7)*
C12	0.8559 (3)	0.24495 (15)	0.72436 (13)	0.0113 (4)
C13	1.0863 (3)	0.29809 (15)	0.71971 (14)	0.0145 (4)
H13A	1.1811	0.2563	0.7388	0.017*
H13B	1.1111	0.3024	0.6561	0.017*
C14	1.1355 (3)	0.40791 (16)	0.78235 (14)	0.0157 (4)
H14	1.2854	0.4421	0.7784	0.019*
C15	0.9883 (3)	0.47258 (16)	0.75293 (14)	0.0172 (4)
H15A	1.0211	0.5437	0.7928	0.021*
H15B	1.0101	0.4781	0.6894	0.021*
C16	0.7587 (3)	0.42114 (16)	0.75939 (13)	0.0154 (4)
H16	0.6633	0.4637	0.7403	0.019*
C17	0.7099 (3)	0.31176 (15)	0.69597 (13)	0.0131 (4)
H17A	0.7303	0.3170	0.6323	0.016*
H17B	0.5610	0.2781	0.6989	0.016*
C18	0.7244 (3)	0.41275 (16)	0.85783 (13)	0.0173 (4)
H18A	0.7535	0.4831	0.8989	0.021*
H18B	0.5760	0.3791	0.8619	0.021*
C19	0.8716 (3)	0.34845 (16)	0.88730 (14)	0.0167 (4)
H19	0.8498	0.3433	0.9516	0.020*
C20	1.1009 (3)	0.40095 (16)	0.88100 (14)	0.0181 (5)
H20A	1.1967	0.3603	0.9011	0.022*
H20B	1.1332	0.4716	0.9216	0.022*
C21	0.8212 (3)	0.23899 (16)	0.82383 (13)	0.0148 (4)
H21A	0.6729	0.2053	0.8280	0.018*
H21B	0.9132	0.1961	0.8434	0.018*
C22	0.8034 (3)	0.13331 (15)	0.66746 (13)	0.0135 (4)
H22A	0.8908	0.0923	0.6928	0.016*
H22B	0.6538	0.1027	0.6727	0.016*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0178 (3)	0.0247 (3)	0.0229 (3)	0.0049 (2)	0.0017 (2)	0.0091 (2)
O1	0.0399 (11)	0.0353 (12)	0.0310 (11)	0.0050 (9)	0.0045 (9)	0.0126 (10)
N1	0.0183 (10)	0.0238 (11)	0.0151 (10)	0.0056 (9)	0.0019 (8)	0.0071 (8)
C1	0.0111 (9)	0.0120 (10)	0.0140 (10)	0.0014 (8)	0.0006 (8)	0.0037 (8)
C2	0.0119 (10)	0.0136 (10)	0.0197 (11)	0.0041 (8)	0.0023 (8)	0.0035 (9)
C3	0.0145 (10)	0.0123 (10)	0.0194 (11)	0.0052 (8)	−0.0013 (8)	0.0043 (8)
C4	0.0187 (11)	0.0146 (11)	0.0162 (11)	0.0026 (9)	−0.0006 (9)	0.0070 (9)
C5	0.0100 (10)	0.0165 (11)	0.0152 (10)	0.0008 (8)	0.0025 (8)	0.0045 (8)
C6	0.0111 (10)	0.0144 (10)	0.0138 (10)	0.0029 (8)	−0.0010 (8)	0.0034 (8)
C7	0.0189 (11)	0.0192 (11)	0.0150 (11)	0.0079 (9)	0.0034 (9)	0.0037 (9)
C8	0.0179 (11)	0.0142 (11)	0.0137 (10)	0.0027 (9)	−0.0021 (8)	−0.0002 (8)
C9	0.0146 (10)	0.0188 (11)	0.0179 (11)	0.0013 (9)	−0.0054 (8)	0.0052 (9)
C10	0.0143 (10)	0.0107 (10)	0.0204 (11)	0.0019 (8)	−0.0006 (8)	0.0036 (8)
C11	0.0140 (10)	0.0172 (11)	0.0183 (11)	0.0007 (9)	0.0006 (8)	0.0061 (9)
Cl2	0.0146 (2)	0.0168 (3)	0.0135 (2)	0.0022 (2)	−0.00028 (19)	0.00194 (19)
O2	0.0235 (8)	0.0231 (9)	0.0205 (8)	0.0020 (7)	−0.0008 (7)	0.0018 (7)
C23	0.0159 (11)	0.0221 (13)	0.0420 (15)	0.0058 (10)	0.0027 (10)	−0.0034 (11)
C24	0.0343 (14)	0.0258 (13)	0.0270 (13)	−0.0027 (11)	0.0181 (11)	0.0018 (10)
N2	0.0175 (10)	0.0147 (10)	0.0136 (9)	0.0033 (8)	−0.0004 (8)	−0.0013 (8)
C12	0.0111 (9)	0.0121 (10)	0.0102 (9)	0.0019 (8)	−0.0001 (8)	0.0019 (8)
C13	0.0103 (10)	0.0169 (11)	0.0155 (10)	0.0023 (8)	0.0013 (8)	0.0025 (8)
C14	0.0114 (10)	0.0133 (10)	0.0189 (11)	−0.0015 (8)	0.0018 (8)	0.0001 (8)
C15	0.0226 (11)	0.0119 (11)	0.0163 (11)	0.0024 (9)	0.0033 (9)	0.0026 (8)
C16	0.0157 (10)	0.0163 (11)	0.0155 (11)	0.0057 (9)	0.0012 (8)	0.0040 (8)
C17	0.0117 (10)	0.0170 (11)	0.0115 (10)	0.0044 (8)	−0.0002 (8)	0.0042 (8)
C18	0.0173 (11)	0.0182 (11)	0.0153 (11)	0.0041 (9)	0.0042 (8)	0.0010 (9)
C19	0.0195 (11)	0.0201 (11)	0.0103 (10)	0.0038 (9)	0.0023 (8)	0.0033 (8)
C20	0.0186 (11)	0.0169 (11)	0.0158 (11)	0.0019 (9)	−0.0032 (9)	0.0000 (9)
C21	0.0152 (10)	0.0172 (11)	0.0130 (10)	0.0022 (9)	0.0013 (8)	0.0065 (8)
C22	0.0133 (10)	0.0129 (10)	0.0139 (10)	0.0013 (8)	0.0013 (8)	0.0039 (8)

Geometric parameters (Å, º)

O1—H1D	0.82 (3)	C23—H23B	0.9900
O1—H1E	0.91 (4)	C23—C24^i	1.493 (3)
N1—H1A	0.85 (3)	C24—C23^i	1.493 (3)
N1—H1B	0.89 (3)	C24—H24A	0.9900
N1—H1C	0.98 (3)	C24—H24B	0.9900
N1—C11	1.494 (3)	N2—H2C	0.86 (2)
C1—C2	1.547 (3)	N2—H2D	0.86 (3)
C1—C6	1.537 (3)	N2—H2E	0.90 (3)
C1—C10	1.544 (3)	N2—C22	1.493 (3)
C1—C11	1.523 (3)	C12—C13	1.536 (3)
C2—H2A	0.9900	C12—C17	1.543 (3)
C2—H2B	0.9900	C12—C21	1.542 (3)
C2—C3	1.535 (3)	C12—C22	1.523 (3)
C3—H3	1.0000	C13—H13A	0.9900
C3—C4	1.535 (3)	C13—H13B	0.9900
C3—C9	1.529 (3)	C13—C14	1.535 (3)
C4—H4A	0.9900	C14—H14	1.0000
C4—H4B	0.9900	C14—C15	1.533 (3)
C4—C5	1.533 (3)	C14—C20	1.533 (3)
C5—H5	1.0000	C15—H15A	0.9900
C5—C6	1.537 (3)	C15—H15B	0.9900
C5—C7	1.535 (3)	C15—C16	1.530 (3)
C6—H6A	0.9900	C16—H16	1.0000
C6—H6B	0.9900	C16—C17	1.535 (3)
C7—H7A	0.9900	C16—C18	1.534 (3)
C7—H7B	0.9900	C17—H17A	0.9900
C7—C8	1.532 (3)	C17—H17B	0.9900
C8—H8	1.0000	C18—H18A	0.9900
C8—C9	1.532 (3)	C18—H18B	0.9900
C8—C10	1.531 (3)	C18—C19	1.530 (3)
C9—H9A	0.9900	C19—H19	1.0000
C9—H9B	0.9900	C19—C20	1.531 (3)
C10—H10A	0.9900	C19—C21	1.536 (3)
C10—H10B	0.9900	C20—H20A	0.9900
C11—H11A	0.9900	C20—H20B	0.9900
C11—H11B	0.9900	C21—H21A	0.9900
O2—C23	1.429 (3)	C21—H21B	0.9900
O2—C24	1.425 (3)	C22—H22A	0.9900
C23—H23A	0.9900	C22—H22B	0.9900
H1D—O1—H1E	102 (3)	C24^i—C23—H23B	109.5
H1A—N1—H1B	105 (2)	O2—C24—C23^i	111.48 (18)
H1A—N1—H1C	106 (2)	O2—C24—H24A	109.3
H1B—N1—H1C	111 (2)	O2—C24—H24B	109.3
C11—N1—H1A	108.3 (17)	C23^i—C24—H24A	109.3
C11—N1—H1B	113.6 (16)	C23^i—C24—H24B	109.3
C11—N1—H1C	112.3 (16)	H24A—C24—H24B	108.0
C6—C1—C2	108.98 (16)	H2C—N2—H2D	106 (2)
C6—C1—C10	108.68 (16)	H2C—N2—H2E	105 (2)
C10—C1—C2	108.41 (16)	H2D—N2—H2E	108 (2)
C11—C1—C2	111.88 (16)	C22—N2—H2C	109.5 (15)
C11—C1—C6	111.96 (16)	C22—N2—H2D	116.8 (16)
C11—C1—C10	106.81 (16)	C22—N2—H2E	110.1 (16)
C1—C2—H2A	109.7	C13—C12—C17	109.06 (16)
C1—C2—H2B	109.7	C13—C12—C21	108.64 (16)
H2A—C2—H2B	108.2	C21—C12—C17	108.24 (15)
C3—C2—C1	109.98 (15)	C22—C12—C13	112.02 (15)
C3—C2—H2A	109.7	C22—C12—C17	112.31 (16)
C3—C2—H2B	109.7	C22—C12—C21	106.42 (15)
C2—C3—H3	109.4	C12—C13—H13A	109.6
C4—C3—C2	109.32 (16)	C12—C13—H13B	109.6
C4—C3—H3	109.4	H13A—C13—H13B	108.1
C9—C3—C2	109.66 (16)	C14—C13—C12	110.21 (15)
C9—C3—H3	109.4	C14—C13—H13A	109.6
C9—C3—C4	109.58 (16)	C14—C13—H13B	109.6
C3—C4—H4A	109.8	C13—C14—H14	109.6
C3—C4—H4B	109.8	C15—C14—C13	109.61 (16)
H4A—C4—H4B	108.2	C15—C14—H14	109.6
C5—C4—C3	109.55 (16)	C20—C14—C13	109.53 (17)
C5—C4—H4A	109.8	C20—C14—H14	109.6
C5—C4—H4B	109.8	C20—C14—C15	108.95 (16)
C4—C5—H5	109.5	C14—C15—H15A	109.7
C4—C5—C6	109.41 (15)	C14—C15—H15B	109.7
C4—C5—C7	109.42 (16)	H15A—C15—H15B	108.2
C6—C5—H5	109.5	C16—C15—C14	109.89 (16)
C7—C5—H5	109.5	C16—C15—H15A	109.7
C7—C5—C6	109.35 (16)	C16—C15—H15B	109.7
C1—C6—C5	110.25 (16)	C15—C16—H16	109.6
C1—C6—H6A	109.6	C15—C16—C17	108.88 (16)
C1—C6—H6B	109.6	C15—C16—C18	109.79 (17)
C5—C6—H6A	109.6	C17—C16—H16	109.6
C5—C6—H6B	109.6	C18—C16—H16	109.6
H6A—C6—H6B	108.1	C18—C16—C17	109.39 (16)
C5—C7—H7A	109.8	C12—C17—H17A	109.6
C5—C7—H7B	109.8	C12—C17—H17B	109.6
H7A—C7—H7B	108.2	C16—C17—C12	110.35 (16)
C8—C7—C5	109.49 (16)	C16—C17—H17A	109.6
C8—C7—H7A	109.8	C16—C17—H17B	109.6
C8—C7—H7B	109.8	H17A—C17—H17B	108.1
C7—C8—H8	109.4	C16—C18—H18A	109.8
C9—C8—C7	109.42 (17)	C16—C18—H18B	109.8
C9—C8—H8	109.4	H18A—C18—H18B	108.2
C10—C8—C7	109.55 (16)	C19—C18—C16	109.57 (16)
C10—C8—H8	109.4	C19—C18—H18A	109.8
C10—C8—C9	109.59 (16)	C19—C18—H18B	109.8
C3—C9—C8	109.52 (16)	C18—C19—H19	109.6
C3—C9—H9A	109.8	C18—C19—C20	109.50 (17)
C3—C9—H9B	109.8	C18—C19—C21	108.92 (17)
C8—C9—H9A	109.8	C20—C19—H19	109.6
C8—C9—H9B	109.8	C20—C19—C21	109.70 (16)
H9A—C9—H9B	108.2	C21—C19—H19	109.6
C1—C10—H10A	109.6	C14—C20—H20A	109.7
C1—C10—H10B	109.6	C14—C20—H20B	109.7
C8—C10—C1	110.29 (16)	C19—C20—C14	109.72 (16)
C8—C10—H10A	109.6	C19—C20—H20A	109.7
C8—C10—H10B	109.6	C19—C20—H20B	109.7
H10A—C10—H10B	108.1	H20A—C20—H20B	108.2
N1—C11—C1	113.76 (17)	C12—C21—H21A	109.6
N1—C11—H11A	108.8	C12—C21—H21B	109.6
N1—C11—H11B	108.8	C19—C21—C12	110.50 (16)
C1—C11—H11A	108.8	C19—C21—H21A	109.6
C1—C11—H11B	108.8	C19—C21—H21B	109.6
H11A—C11—H11B	107.7	H21A—C21—H21B	108.1
C24—O2—C23	109.78 (16)	N2—C22—C12	113.72 (16)
O2—C23—H23A	109.5	N2—C22—H22A	108.8
O2—C23—H23B	109.5	N2—C22—H22B	108.8
O2—C23—C24^i	110.56 (18)	C12—C22—H22A	108.8
H23A—C23—H23B	108.1	C12—C22—H22B	108.8
C24^i—C23—H23A	109.5	H22A—C22—H22B	107.7
C1—C2—C3—C4	−60.0 (2)	C24—O2—C23—C24^i	−56.6 (3)
C1—C2—C3—C9	60.1 (2)	C12—C13—C14—C15	−59.2 (2)
C2—C1—C6—C5	−58.9 (2)	C12—C13—C14—C20	60.3 (2)
C2—C1—C10—C8	59.2 (2)	C13—C12—C17—C16	−59.1 (2)
C2—C1—C11—N1	−64.9 (2)	C13—C12—C21—C19	58.9 (2)
C2—C3—C4—C5	60.5 (2)	C13—C12—C22—N2	−58.5 (2)
C2—C3—C9—C8	−60.0 (2)	C13—C14—C15—C16	60.1 (2)
C3—C4—C5—C6	−60.2 (2)	C13—C14—C20—C19	−59.6 (2)
C3—C4—C5—C7	59.6 (2)	C14—C15—C16—C17	−60.3 (2)
C4—C3—C9—C8	60.0 (2)	C14—C15—C16—C18	59.5 (2)
C4—C5—C6—C1	59.8 (2)	C15—C14—C20—C19	60.3 (2)
C4—C5—C7—C8	−59.9 (2)	C15—C16—C17—C12	60.1 (2)
C5—C7—C8—C9	60.2 (2)	C15—C16—C18—C19	−59.1 (2)
C5—C7—C8—C10	−60.0 (2)	C16—C18—C19—C20	59.5 (2)
C6—C1—C2—C3	59.0 (2)	C16—C18—C19—C21	−60.4 (2)
C6—C1—C10—C8	−59.1 (2)	C17—C12—C13—C14	58.4 (2)
C6—C1—C11—N1	57.8 (2)	C17—C12—C21—C19	−59.4 (2)
C6—C5—C7—C8	59.9 (2)	C17—C12—C22—N2	64.6 (2)
C7—C5—C6—C1	−60.0 (2)	C17—C16—C18—C19	60.3 (2)
C7—C8—C9—C3	−60.2 (2)	C18—C16—C17—C12	−59.9 (2)
C7—C8—C10—C1	59.9 (2)	C18—C19—C20—C14	−60.4 (2)
C9—C3—C4—C5	−59.7 (2)	C18—C19—C21—C12	60.7 (2)
C9—C8—C10—C1	−60.1 (2)	C20—C14—C15—C16	−59.8 (2)
C10—C1—C2—C3	−59.1 (2)	C20—C19—C21—C12	−59.1 (2)
C10—C1—C6—C5	59.1 (2)	C21—C12—C13—C14	−59.4 (2)
C10—C1—C11—N1	176.65 (16)	C21—C12—C17—C16	58.9 (2)
C10—C8—C9—C3	59.9 (2)	C21—C12—C22—N2	−177.13 (16)
C11—C1—C2—C3	−176.61 (16)	C21—C19—C20—C14	59.0 (2)
C11—C1—C6—C5	176.84 (16)	C22—C12—C13—C14	−176.66 (16)
C11—C1—C10—C8	179.95 (15)	C22—C12—C17—C16	176.07 (15)
C23—O2—C24—C23^i	57.1 (3)	C22—C12—C21—C19	179.66 (15)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1D···Cl2^ii	0.82 (3)	2.48 (3)	3.295 (2)	175 (3)
O1—H1E···Cl1	0.91 (4)	2.36 (4)	3.265 (2)	180 (3)
N1—H1A···Cl2^iii	0.85 (3)	2.33 (3)	3.161 (2)	163 (2)
N1—H1B···O2	0.89 (3)	2.10 (3)	2.867 (3)	144 (2)
N1—H1C···Cl1	0.98 (3)	2.19 (3)	3.152 (2)	166 (2)
N2—H2C···Cl2^ii	0.86 (2)	2.31 (3)	3.166 (2)	172 (2)
N2—H2D···Cl1	0.86 (3)	2.48 (3)	3.171 (2)	138 (2)
N2—H2E···Cl2	0.90 (3)	2.30 (3)	3.181 (2)	166 (2)

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