Nafimidone hemihydrate hemi­hydro­chloride

In the crystal structure of the title compound, 2-(1H-imidazol-1-yl)-1-(2-naphthyl)ethanone hemihydrate hemihydro­chlo­ride, 2C₁₅H₁₃N₂O₂·H₂O·HCl or C₃₀H₂₅N₄O₄⁺·Cl^-·H₂O, there are two independent mol­ecules of nafimidone in the asymmetric unit. The imidazole and the naphthalene rings in both mol­ecules are planar. The water mol­ecule is hydrogen bonded to Cl^- ions. The protonation occurs at the unsubstituted N atom in both mol­ecules, with 50% occupancy, linking the molecules together by hydrogen bonding. A network of weak non-standard hydrogen bonds exists in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.052
• wR factor = 0.162
• Data-to-parameter ratio = 9.6

checkCIF/PLATON results

No syntax errors found



Alert level A
THETM01_ALERT_3_A  The value of sine(theta_max)/wavelength is less than 0.550
            Calculated sin(theta_max)/wavelength =    0.5312

Author Response: ...'see _exptl_special_details'

PLAT023_ALERT_3_A Resolution (too) Low [sin(th)/Lambda < 0.6].....      54.99 Deg.

Author Response: ...'see _exptl_special_details'

PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      54.99 Deg.

Author Response: ...'see _exptl_special_details'

PLAT355_ALERT_3_A Long    O-H Bond (0.82A)   O      -   H1W    ...       1.16 Ang.

Author Response: ...'see _exptl_special_details'

Alert level C
REFNR01_ALERT_3_C  Ratio of reflections to parameters is < 10 for a
            centrosymmetric structure
            sine(theta)/lambda                0.5312
            Proportion of unique data used    1.0000
            Ratio reflections to parameters   9.5931
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       9.59
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.07
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O      -   H2W    ...       1.06 Ang.

Author Response: ...'see _exptl_special_details'

PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C30 H25 N4 O2
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              H2 O
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          4
              Cl

   4 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   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
   8 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: Picker Operating Manual (Picker, 1967); cell refinement: Picker Operating Manual; data reduction: DATRDN (Stewart, 1976); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

3-methyl-1-[2-(2-naphthyloxy)ethyl]-1H-pyrazol-5-ol hydrochloride monohydrate

Crystal data

C30H25N4O2^+·Cl^−·H2O	Z = 2
Mr = 527.01	F(000) = 552
Triclinic, P1	Dx = 1.308 Mg m^−3
a = 9.171 (3) Å	Cu Kα radiation, λ = 1.54178 Å
b = 9.428 (2) Å	Cell parameters from 32 reflections
c = 16.783 (2) Å	θ = 31–52°
α = 77.19 (1)°	µ = 1.58 mm^−1
β = 75.44 (1)°	T = 294 K
γ = 75.11 (1)°	Needle, colorless
V = 1338.1 (6) Å^3	0.51 × 0.13 × 0.08 mm

Data collection

Picker FACS-1 four-circle diffractometer	2773 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
Ni-filtered radiation monochromator	θmax = 55.0°, θmin = 2.8°
θ/2θ scans	h = −9→9
Absorption correction: ψ scan (North et al., 1968)	k = −10→0
Tmin = 0.785, Tmax = 0.885	l = −17→17
3600 measured reflections	3 standard reflections every 100 reflections
3348 independent reflections	intensity decay: 0.6%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.162	w = 1/[σ^2(Fo^2) + (0.0929P)^2 + 0.2986P] where P = (Fo^2 + 2Fc^2)/3
S = 1.18	(Δ/σ)max < 0.001
3348 reflections	Δρmax = 0.63 e Å^−3
349 parameters	Δρmin = −0.21 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0064 (10)

Special details

Experimental. No observable reflections above 55° in θ

H atoms from the water molecule were found from the difference map and were fixed in the found positions because they wandered randomly when subject to refinement.

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)
C1A	0.4926 (3)	0.1050 (3)	0.14386 (18)	0.0553 (7)
H1A	0.5872	0.0592	0.1148	0.078 (2)*
C2A	0.4734 (3)	0.1059 (3)	0.22720 (18)	0.0548 (7)
C3A	0.3291 (3)	0.1726 (4)	0.2718 (2)	0.0664 (9)
H3A	0.3155	0.1724	0.3286	0.078 (2)*
C4A	0.2097 (4)	0.2374 (4)	0.2324 (2)	0.0673 (9)
H4A	0.1153	0.2810	0.2627	0.078 (2)*
C5A	0.1035 (4)	0.3086 (4)	0.1030 (2)	0.0719 (9)
H5A	0.0081	0.3540	0.1315	0.078 (2)*
C6A	0.1264 (4)	0.3074 (4)	0.0200 (2)	0.0750 (10)
H6A	0.0459	0.3516	−0.0078	0.078 (2)*
C7A	0.2682 (5)	0.2411 (4)	−0.0241 (2)	0.0777 (10)
H7A	0.2809	0.2409	−0.0808	0.078 (2)*
C8A	0.3887 (4)	0.1767 (4)	0.01466 (19)	0.0655 (8)
H8A	0.4836	0.1349	−0.0160	0.078 (2)*
C9A	0.3704 (3)	0.1730 (3)	0.10078 (18)	0.0553 (7)
C10A	0.2272 (3)	0.2393 (3)	0.14689 (19)	0.0586 (8)
N11A	0.7319 (3)	−0.0092 (3)	0.38835 (14)	0.0577 (7)
C12A	0.7392 (4)	−0.1299 (4)	0.44600 (18)	0.0630 (8)
H12A	0.6590	−0.1793	0.4703	0.078 (2)*
N13A	0.8781 (3)	−0.1698 (3)	0.46392 (16)	0.0693 (7)
H13A	0.9096	−0.2447	0.4998	0.078 (2)*	0.50
C14A	0.9618 (4)	−0.0707 (4)	0.4152 (2)	0.0745 (10)
H14A	1.0637	−0.0718	0.4147	0.078 (2)*
C15A	0.8721 (4)	0.0284 (4)	0.3681 (2)	0.0702 (9)
H15A	0.9001	0.1084	0.3287	0.078 (2)*
C16A	0.6081 (3)	0.0360 (3)	0.26768 (18)	0.0562 (7)
C17A	0.5959 (3)	0.0662 (4)	0.35420 (19)	0.0623 (8)
H17A	0.5807	0.1725	0.3520	0.075 (5)*
H17B	0.5064	0.0338	0.3912	0.075 (5)*
O18A	0.7224 (3)	−0.0425 (3)	0.23380 (14)	0.0798 (7)
C1B	1.5377 (3)	−0.6721 (3)	0.77010 (18)	0.0564 (8)
H1B	1.5323	−0.7268	0.7315	0.078 (2)*
C2B	1.4294 (3)	−0.5446 (3)	0.78242 (17)	0.0552 (7)
C3B	1.4367 (4)	−0.4607 (4)	0.8407 (2)	0.0685 (9)
H3B	1.3631	−0.3739	0.8490	0.078 (2)*
C4B	1.5515 (4)	−0.5068 (4)	0.8848 (2)	0.0726 (9)
H4B	1.5557	−0.4499	0.9226	0.078 (2)*
C5B	1.7798 (5)	−0.6905 (5)	0.9211 (2)	0.0875 (11)
H5B	1.7844	−0.6371	0.9605	0.078 (2)*
C6B	1.8853 (5)	−0.8181 (5)	0.9094 (3)	0.0963 (13)
H6B	1.9607	−0.8517	0.9413	0.078 (2)*
C7B	1.8828 (4)	−0.8998 (4)	0.8505 (3)	0.0818 (11)
H7B	1.9571	−0.9865	0.8429	0.078 (2)*
C8B	1.7714 (3)	−0.8533 (4)	0.8037 (2)	0.0666 (8)
H8B	1.7703	−0.9083	0.7643	0.078 (2)*
C9B	1.6584 (3)	−0.7224 (3)	0.81530 (18)	0.0579 (8)
C10B	1.6634 (4)	−0.6380 (4)	0.8744 (2)	0.0648 (8)
N11B	1.1356 (3)	−0.5390 (3)	0.65417 (15)	0.0572 (7)
C12B	1.1152 (4)	−0.4241 (4)	0.59240 (19)	0.0647 (8)
H12B	1.1896	−0.3701	0.5630	0.078 (2)*
N13B	0.9751 (3)	−0.3984 (3)	0.57924 (16)	0.0685 (7)
H13B	0.9358	−0.3295	0.5428	0.078 (2)*	0.50
C14B	0.9040 (4)	−0.5013 (4)	0.6341 (2)	0.0704 (9)
H14B	0.8036	−0.5103	0.6382	0.078 (2)*
C15B	1.0011 (4)	−0.5872 (4)	0.6810 (2)	0.0659 (8)
H15B	0.9808	−0.6653	0.7241	0.078 (2)*
C16B	1.3010 (3)	−0.4924 (3)	0.73733 (18)	0.0588 (8)
C17B	1.2744 (3)	−0.5977 (3)	0.6883 (2)	0.0625 (8)
H17C	1.3626	−0.6160	0.6430	0.075 (5)*
H17D	1.2662	−0.6921	0.7247	0.075 (5)*
O18B	1.2168 (3)	−0.3697 (3)	0.73986 (15)	0.0816 (7)
O	0.5633 (4)	−0.4181 (4)	0.57337 (18)	0.1030 (9)
Cl	0.37410 (7)	−0.21618 (8)	0.44084 (4)	0.0608 (3)
H1W	0.4975	−0.339 (6)	0.5239	0.155 (14)*
H2W	0.6183	−0.529 (6)	0.5645	0.155 (14)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0514 (17)	0.0452 (16)	0.0693 (19)	−0.0065 (13)	−0.0116 (14)	−0.0147 (13)
C2A	0.0522 (17)	0.0503 (17)	0.0639 (18)	−0.0071 (14)	−0.0168 (13)	−0.0126 (14)
C3A	0.0553 (19)	0.078 (2)	0.0680 (19)	−0.0012 (16)	−0.0194 (15)	−0.0243 (16)
C4A	0.0529 (18)	0.073 (2)	0.076 (2)	0.0026 (16)	−0.0176 (15)	−0.0270 (17)
C5A	0.062 (2)	0.064 (2)	0.095 (3)	−0.0048 (16)	−0.0341 (18)	−0.0138 (18)
C6A	0.084 (3)	0.062 (2)	0.087 (2)	−0.0125 (19)	−0.046 (2)	−0.0006 (18)
C7A	0.092 (3)	0.067 (2)	0.074 (2)	−0.020 (2)	−0.028 (2)	0.0023 (18)
C8A	0.075 (2)	0.0589 (19)	0.065 (2)	−0.0179 (16)	−0.0181 (16)	−0.0066 (15)
C9A	0.0541 (18)	0.0438 (16)	0.0700 (19)	−0.0096 (14)	−0.0182 (14)	−0.0085 (13)
C10A	0.0580 (18)	0.0478 (17)	0.0726 (19)	−0.0080 (14)	−0.0211 (15)	−0.0105 (14)
N11A	0.0547 (15)	0.0587 (16)	0.0623 (15)	−0.0101 (12)	−0.0216 (11)	−0.0068 (12)
C12A	0.066 (2)	0.064 (2)	0.0608 (18)	−0.0134 (16)	−0.0196 (15)	−0.0065 (16)
N13A	0.0727 (18)	0.0705 (18)	0.0673 (16)	−0.0081 (15)	−0.0310 (14)	−0.0065 (14)
C14A	0.063 (2)	0.085 (2)	0.083 (2)	−0.0179 (19)	−0.0291 (18)	−0.012 (2)
C15A	0.065 (2)	0.070 (2)	0.079 (2)	−0.0220 (17)	−0.0262 (17)	0.0018 (17)
C16A	0.0508 (18)	0.0493 (17)	0.0686 (18)	−0.0070 (15)	−0.0158 (14)	−0.0102 (14)
C17A	0.0562 (18)	0.0605 (19)	0.0698 (19)	−0.0008 (15)	−0.0227 (15)	−0.0128 (15)
O18A	0.0619 (14)	0.0854 (16)	0.0873 (16)	0.0114 (13)	−0.0235 (12)	−0.0268 (13)
C1B	0.0572 (18)	0.0560 (18)	0.0583 (17)	−0.0161 (15)	−0.0150 (13)	−0.0060 (14)
C2B	0.0536 (17)	0.0471 (17)	0.0621 (17)	−0.0128 (14)	−0.0095 (13)	−0.0035 (13)
C3B	0.077 (2)	0.0539 (19)	0.077 (2)	−0.0177 (17)	−0.0138 (17)	−0.0144 (16)
C4B	0.090 (2)	0.066 (2)	0.075 (2)	−0.029 (2)	−0.0242 (18)	−0.0159 (17)
C5B	0.093 (3)	0.084 (3)	0.106 (3)	−0.032 (2)	−0.050 (2)	−0.009 (2)
C6B	0.099 (3)	0.088 (3)	0.121 (3)	−0.032 (3)	−0.066 (3)	0.008 (3)
C7B	0.064 (2)	0.062 (2)	0.122 (3)	−0.0147 (17)	−0.039 (2)	0.003 (2)
C8B	0.0580 (19)	0.0564 (19)	0.088 (2)	−0.0170 (16)	−0.0209 (16)	−0.0044 (16)
C9B	0.0569 (18)	0.0541 (18)	0.0661 (18)	−0.0233 (15)	−0.0170 (14)	0.0015 (14)
C10B	0.069 (2)	0.061 (2)	0.072 (2)	−0.0284 (17)	−0.0230 (16)	−0.0012 (16)
N11B	0.0477 (14)	0.0579 (16)	0.0644 (15)	−0.0100 (11)	−0.0157 (11)	−0.0041 (12)
C12B	0.060 (2)	0.065 (2)	0.0600 (18)	−0.0124 (16)	−0.0093 (15)	0.0028 (16)
N13B	0.0664 (18)	0.0730 (18)	0.0653 (16)	−0.0042 (14)	−0.0268 (13)	−0.0072 (14)
C14B	0.0537 (19)	0.073 (2)	0.089 (2)	−0.0156 (17)	−0.0217 (17)	−0.0118 (19)
C15B	0.0555 (19)	0.065 (2)	0.078 (2)	−0.0212 (16)	−0.0185 (16)	0.0019 (16)
C16B	0.0573 (18)	0.0502 (19)	0.0626 (18)	−0.0072 (15)	−0.0098 (14)	−0.0045 (14)
C17B	0.0484 (17)	0.0590 (19)	0.079 (2)	−0.0048 (14)	−0.0207 (15)	−0.0090 (15)
O18B	0.0821 (16)	0.0612 (15)	0.0982 (17)	0.0060 (13)	−0.0293 (13)	−0.0192 (12)
O	0.112 (2)	0.104 (2)	0.107 (2)	−0.0268 (18)	−0.0455 (16)	−0.0154 (16)
Cl	0.0430 (5)	0.0718 (5)	0.0649 (5)	−0.0138 (3)	−0.0077 (3)	−0.0079 (4)

Geometric parameters (Å, º)

C1A—C2A	1.367 (4)	C1B—C9B	1.421 (4)
C1A—C9A	1.422 (4)	C1B—H1B	0.9300
C1A—H1A	0.9300	C2B—C3B	1.411 (4)
C2A—C3A	1.411 (4)	C2B—C16B	1.479 (4)
C2A—C16A	1.492 (4)	C3B—C4B	1.363 (5)
C3A—C4A	1.360 (4)	C3B—H3B	0.9300
C3A—H3A	0.9300	C4B—C10B	1.403 (5)
C4A—C10A	1.401 (4)	C4B—H4B	0.9300
C4A—H4A	0.9300	C5B—C6B	1.354 (6)
C5A—C6A	1.356 (5)	C5B—C10B	1.406 (5)
C5A—C10A	1.444 (4)	C5B—H5B	0.9300
C5A—H5A	0.9300	C6B—C7B	1.388 (6)
C6A—C7A	1.390 (5)	C6B—H6B	0.9300
C6A—H6A	0.9300	C7B—C8B	1.368 (5)
C7A—C8A	1.362 (5)	C7B—H7B	0.9300
C7A—H7A	0.9300	C8B—C9B	1.408 (4)
C8A—C9A	1.406 (4)	C8B—H8B	0.9300
C8A—H8A	0.9300	C9B—C10B	1.418 (4)
C9A—C10A	1.412 (4)	N11B—C12B	1.334 (4)
N11A—C12A	1.319 (4)	N11B—C15B	1.360 (4)
N11A—C15A	1.362 (4)	N11B—C17B	1.456 (4)
N11A—C17A	1.453 (3)	C12B—N13B	1.311 (4)
C12A—N13A	1.323 (4)	C12B—H12B	0.9300
C12A—H12A	0.9300	N13B—C14B	1.357 (4)
N13A—C14A	1.359 (4)	N13B—H13B	0.8600
N13A—H13A	0.8600	C14B—C15B	1.330 (4)
C14A—C15A	1.333 (4)	C14B—H14B	0.9300
C14A—H14A	0.9300	C15B—H15B	0.9300
C15A—H15A	0.9300	C16B—O18B	1.218 (4)
C16A—O18A	1.208 (3)	C16B—C17B	1.519 (4)
C16A—C17A	1.512 (4)	C17B—H17C	0.9700
C17A—H17A	0.9700	C17B—H17D	0.9700
C17A—H17B	0.9700	O—H1W	1.165 (18)
C1B—C2B	1.366 (4)	O—H2W	1.06 (5)
C2A—C1A—C9A	121.1 (3)	C2B—C1B—H1B	119.5
C2A—C1A—H1A	119.4	C9B—C1B—H1B	119.5
C9A—C1A—H1A	119.4	C1B—C2B—C3B	119.9 (3)
C1A—C2A—C3A	119.6 (3)	C1B—C2B—C16B	121.8 (3)
C1A—C2A—C16A	118.1 (2)	C3B—C2B—C16B	118.3 (3)
C3A—C2A—C16A	122.3 (3)	C4B—C3B—C2B	120.1 (3)
C4A—C3A—C2A	120.6 (3)	C4B—C3B—H3B	120.0
C4A—C3A—H3A	119.7	C2B—C3B—H3B	120.0
C2A—C3A—H3A	119.7	C3B—C4B—C10B	121.5 (3)
C3A—C4A—C10A	120.8 (3)	C3B—C4B—H4B	119.3
C3A—C4A—H4A	119.6	C10B—C4B—H4B	119.3
C10A—C4A—H4A	119.6	C6B—C5B—C10B	120.7 (4)
C6A—C5A—C10A	119.9 (3)	C6B—C5B—H5B	119.7
C6A—C5A—H5A	120.0	C10B—C5B—H5B	119.7
C10A—C5A—H5A	120.0	C5B—C6B—C7B	121.2 (4)
C5A—C6A—C7A	121.1 (3)	C5B—C6B—H6B	119.4
C5A—C6A—H6A	119.4	C7B—C6B—H6B	119.4
C7A—C6A—H6A	119.4	C8B—C7B—C6B	120.3 (4)
C8A—C7A—C6A	120.9 (3)	C8B—C7B—H7B	119.9
C8A—C7A—H7A	119.6	C6B—C7B—H7B	119.9
C6A—C7A—H7A	119.6	C7B—C8B—C9B	120.1 (3)
C7A—C8A—C9A	120.3 (3)	C7B—C8B—H8B	120.0
C7A—C8A—H8A	119.9	C9B—C8B—H8B	120.0
C9A—C8A—H8A	119.9	C10B—C9B—C8B	119.4 (3)
C8A—C9A—C10A	119.8 (3)	C10B—C9B—C1B	118.5 (3)
C8A—C9A—C1A	122.1 (3)	C8B—C9B—C1B	122.1 (3)
C10A—C9A—C1A	118.1 (3)	C5B—C10B—C4B	122.6 (3)
C4A—C10A—C9A	119.8 (3)	C5B—C10B—C9B	118.5 (3)
C4A—C10A—C5A	122.2 (3)	C4B—C10B—C9B	119.0 (3)
C9A—C10A—C5A	118.0 (3)	C12B—N11B—C15B	107.3 (2)
C12A—N11A—C15A	107.7 (2)	C12B—N11B—C17B	126.1 (3)
C12A—N11A—C17A	124.5 (3)	C15B—N11B—C17B	126.6 (3)
C15A—N11A—C17A	127.8 (3)	N13B—C12B—N11B	110.0 (3)
N11A—C12A—N13A	109.5 (3)	N13B—C12B—H12B	125.0
N11A—C12A—H12A	125.2	N11B—C12B—H12B	125.0
N13A—C12A—H12A	125.2	C12B—N13B—C14B	106.8 (3)
C12A—N13A—C14A	107.4 (3)	C12B—N13B—H13B	126.6
C12A—N13A—H13A	126.3	C14B—N13B—H13B	126.6
C14A—N13A—H13A	126.3	C15B—C14B—N13B	108.9 (3)
C15A—C14A—N13A	108.0 (3)	C15B—C14B—H14B	125.5
C15A—C14A—H14A	126.0	N13B—C14B—H14B	125.5
N13A—C14A—H14A	126.0	C14B—C15B—N11B	106.9 (3)
C14A—C15A—N11A	107.3 (3)	C14B—C15B—H15B	126.5
C14A—C15A—H15A	126.3	N11B—C15B—H15B	126.5
N11A—C15A—H15A	126.3	O18B—C16B—C2B	121.6 (3)
O18A—C16A—C2A	122.1 (3)	O18B—C16B—C17B	120.3 (3)
O18A—C16A—C17A	120.6 (3)	C2B—C16B—C17B	118.1 (3)
C2A—C16A—C17A	117.3 (2)	N11B—C17B—C16B	112.5 (2)
N11A—C17A—C16A	112.7 (2)	N11B—C17B—H17C	109.1
N11A—C17A—H17A	109.0	C16B—C17B—H17C	109.1
C16A—C17A—H17A	109.0	N11B—C17B—H17D	109.1
N11A—C17A—H17B	109.0	C16B—C17B—H17D	109.1
C16A—C17A—H17B	109.0	H17C—C17B—H17D	107.8
H17A—C17A—H17B	107.8	H1W—O—H2W	120 (2)
C2B—C1B—C9B	121.0 (3)
C9A—C1A—C2A—C3A	1.2 (4)	C9B—C1B—C2B—C3B	0.1 (4)
C9A—C1A—C2A—C16A	−178.4 (3)	C9B—C1B—C2B—C16B	−178.6 (3)
C1A—C2A—C3A—C4A	−0.7 (5)	C1B—C2B—C3B—C4B	−0.1 (5)
C16A—C2A—C3A—C4A	178.9 (3)	C16B—C2B—C3B—C4B	178.7 (3)
C2A—C3A—C4A—C10A	0.0 (5)	C2B—C3B—C4B—C10B	−0.7 (5)
C10A—C5A—C6A—C7A	−0.5 (5)	C10B—C5B—C6B—C7B	0.7 (6)
C5A—C6A—C7A—C8A	−0.6 (5)	C5B—C6B—C7B—C8B	−0.9 (6)
C6A—C7A—C8A—C9A	1.5 (5)	C6B—C7B—C8B—C9B	−0.2 (5)
C7A—C8A—C9A—C10A	−1.4 (5)	C7B—C8B—C9B—C10B	1.3 (5)
C7A—C8A—C9A—C1A	179.2 (3)	C7B—C8B—C9B—C1B	−178.0 (3)
C2A—C1A—C9A—C8A	178.4 (3)	C2B—C1B—C9B—C10B	0.7 (4)
C2A—C1A—C9A—C10A	−1.1 (4)	C2B—C1B—C9B—C8B	180.0 (3)
C3A—C4A—C10A—C9A	0.1 (5)	C6B—C5B—C10B—C4B	179.8 (4)
C3A—C4A—C10A—C5A	−179.2 (3)	C6B—C5B—C10B—C9B	0.5 (5)
C8A—C9A—C10A—C4A	−179.1 (3)	C3B—C4B—C10B—C5B	−177.8 (3)
C1A—C9A—C10A—C4A	0.4 (4)	C3B—C4B—C10B—C9B	1.5 (5)
C8A—C9A—C10A—C5A	0.3 (4)	C8B—C9B—C10B—C5B	−1.5 (5)
C1A—C9A—C10A—C5A	179.8 (3)	C1B—C9B—C10B—C5B	177.9 (3)
C6A—C5A—C10A—C4A	180.0 (3)	C8B—C9B—C10B—C4B	179.2 (3)
C6A—C5A—C10A—C9A	0.6 (5)	C1B—C9B—C10B—C4B	−1.4 (4)
C15A—N11A—C12A—N13A	0.6 (3)	C15B—N11B—C12B—N13B	−0.2 (4)
C17A—N11A—C12A—N13A	−179.5 (2)	C17B—N11B—C12B—N13B	−178.0 (3)
N11A—C12A—N13A—C14A	−0.4 (3)	N11B—C12B—N13B—C14B	−0.5 (4)
C12A—N13A—C14A—C15A	0.0 (4)	C12B—N13B—C14B—C15B	1.0 (4)
N13A—C14A—C15A—N11A	0.4 (4)	N13B—C14B—C15B—N11B	−1.1 (4)
C12A—N11A—C15A—C14A	−0.6 (4)	C12B—N11B—C15B—C14B	0.8 (4)
C17A—N11A—C15A—C14A	179.5 (3)	C17B—N11B—C15B—C14B	178.6 (3)
C1A—C2A—C16A—O18A	−13.2 (4)	C1B—C2B—C16B—O18B	−170.1 (3)
C3A—C2A—C16A—O18A	167.2 (3)	C3B—C2B—C16B—O18B	11.1 (4)
C1A—C2A—C16A—C17A	167.3 (3)	C1B—C2B—C16B—C17B	10.9 (4)
C3A—C2A—C16A—C17A	−12.3 (4)	C3B—C2B—C16B—C17B	−167.8 (3)
C12A—N11A—C17A—C16A	−104.0 (3)	C12B—N11B—C17B—C16B	69.8 (4)
C15A—N11A—C17A—C16A	75.8 (4)	C15B—N11B—C17B—C16B	−107.6 (3)
O18A—C16A—C17A—N11A	−0.5 (4)	O18B—C16B—C17B—N11B	−4.9 (4)
C2A—C16A—C17A—N11A	178.9 (2)	C2B—C16B—C17B—N11B	174.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O—H1W···Cl	1.165 (18)	1.992 (15)	3.154 (3)	175 (3)
O—H2W···Cl^i	1.06 (5)	2.41 (6)	3.399 (3)	154.9 (16)
N13A—*H13A···N13B	0.86	1.83	2.686 (4)	177
N13B—*H13B···N13A	0.86	1.83	2.686 (4)	171
C5A—H5A···O18B^ii	0.93	2.59	3.439 (4)	153
C12B—H12B···Cl^iii	0.93	2.72	3.618 (3)	164
C14B—H14B···O	0.93	2.57	3.376 (4)	146
C15A—H15A···O18B^iv	0.93	2.56	3.333 (4)	141
C17A—H17B···Cl	0.97	2.80	3.594 (3)	140
C17B—H17D···O18A^v	0.97	2.43	3.349 (4)	159
C17B—H17C···Cl^v	0.97	2.76	3.666 (3)	155

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