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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.
Supporting information
CCDC reference: 274572
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (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
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]-1
H-pyrazol-5-ol hydrochloride
monohydrate
top
Crystal data top
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) Å3 | 0.51 × 0.13 × 0.08 mm |
Data collection top
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 top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.053 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.162 | w = 1/[σ2(Fo2) + (0.0929P)2 + 0.2986P] where P = (Fo2 + 2Fc2)/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+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0064 (10) |
Special details top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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···Cli | 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···O18Bii | 0.93 | 2.59 | 3.439 (4) | 153 |
C12B—H12B···Cliii | 0.93 | 2.72 | 3.618 (3) | 164 |
C14B—H14B···O | 0.93 | 2.57 | 3.376 (4) | 146 |
C15A—H15A···O18Biv | 0.93 | 2.56 | 3.333 (4) | 141 |
C17A—H17B···Cl | 0.97 | 2.80 | 3.594 (3) | 140 |
C17B—H17D···O18Av | 0.97 | 2.43 | 3.349 (4) | 159 |
C17B—H17C···Clv | 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. |
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