Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270111005488/bi3008sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270111005488/bi3008Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270111005488/bi3008IIsup3.hkl |
CCDC references: 819309; 819310
For related literature, see: Allen (2002); Fabbiani & Dittrich (2008); Fabbiani et al. (2009); Główka et al. (2003); Li et al. (2006); Mahapatra et al. (2010); McKinnon et al. (1998, 2004, 2007); Mitscher (2005); Prasanna & Guru Row (2001); Sheldrick (2008a, 2008b); Spackman & Byrom (1997); Spackman & McKinnon (2002); Turel (2002); Turel & Golobič (2003); Turel et al. (1997).
Ciprofloxacin (Sigma Aldrich) was used as received. Single crystals were obtained by recrystallization from 2,2-difluoroethanol for (I) or from water–NaOH at ca pH 12 for (II), by slow evaporation of saturated solutions under ambient conditions. Crystals of (II) were identified from a mixture also containing crystals of the known Cf hexahydrate. They can be easily distinguished by their characteristic thick block habit, compared with the thin plates typically displayed by the hexahydrate. While we have not studied in detail the conditions under which preferential or controlled crystallization of (II) occurs, we have also observed concomitant crystallisation of the two hydrates from water–NaOH (ca pH 12) at the lower temparature of 278 K. These crystals appear to be stable when kept suspended in solution for weeks under ambient conditions. Crystals of (II) have also been obtained by crystallization from an aqueous Ba(OH)2 solution.
For (I), several crystals of various size were screened and all were found to be two-component twins. Smaller crystals were found to be better suited for data collection in terms of low mosaicity and good reflection profiles, e.g. absence of peak splitting, though data resolution was limited even using a synchrotron source. The non-merohedral twin law corresponds to a twofold rotation about the [011] direct-lattice direction. The fractional contribution of the major component was refined to 0.519 (2).
The program TWINABS (Sheldrick, 2008a) was used to generate a merged reflection file for (I) in the SHELXL HKLF5 format (Sheldrick, 2008b). Data statistics were as follows: 20118 data (4526 unique) for domain 1 only with mean I/σ(I) = 14.3; 20116 data (4515 unique) for domain 2 only with mean I/σ(I) = 14.5, and 7592 data (1975 unique) for both domains with mean I/σ(I) = 20.0. The quoted Rint value (0.07) comes from scaling all single and composite reflections involving domain 1. For the generation of an HKLF5 file, all observations containing domain 1 were chosen. Single reflections that also occur in composites were omitted for merging.
Given the low data-to-parameter ratio, non-H atoms of Cf in (I) were subjected to rigid-bond and similarity restraints, and bonds in the two Cf molecules were restrained to be the same with an s.u. of 0.02 Å. In the structure of (II), seven water O atoms (OW1–OW7) were modelled with split sites, with their occupancies set to either 50:50 or 60:40, one O atom (OW14) was modelled as half-occupied and the remaining six as fully occupied. The strategy for assigning site occupancies for OW1–OW7 and OW14 consisted of refining different models in which a variable number of occupancies were fixed and/or allowed to refine, so as to obtain an optimal R factor. Occupancies were fixed in the final refinement.
For both structures, H atoms belonging to Cf were positioned geometrically and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(parent). In both structures, N-bound H atoms in the Cf molecules were clearly visible in a difference Fourier map but were positioned geometrically and constrained to ride during refinement. For (I), hydroxyl H atoms were first located in a difference Fourier map and subsequently constrained to ride on their parent atom using a variable C—C—O—H torsion angle (AFIX 147 instruction in SHELXL97). For (II), H atoms for the eight ordered water molecules were clearly visible in a difference Fourier map. Their positions were refined subject to bond-distance and bond-angle restraints, with Uiso(H) = 1.5Ueq(O). The H atoms of the disordered water molecules could not be located, and they cannot easily be placed to form a consistent hydrogen-bonding pattern. These H atoms were therefore omitted from the structure.
For both compounds, data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: ORTEP-3 for Windows (Burnett & Johnson, 1996) and Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).
2C17H18FN3O3·3C2H4F2O | Z = 2 |
Mr = 908.84 | F(000) = 948 |
Triclinic, P1 | Dx = 1.463 Mg m−3 |
Hall symbol: -P 1 | Synchrotron radiation, λ = 0.7000 Å |
a = 10.9848 (4) Å | Cell parameters from 9991 reflections |
b = 13.9800 (4) Å | θ = 2.3–24.6° |
c = 13.9802 (4) Å | µ = 0.13 mm−1 |
α = 105.6488 (18)° | T = 120 K |
β = 90.352 (2)° | Block, yellow |
γ = 93.364 (2)° | 0.1 × 0.08 × 0.08 mm |
V = 2063.22 (11) Å3 |
Bruker SMART APEXII CCD area-detector diffractometer | 7072 independent reflections |
Radiation source: fine-focus sealed tube | 5962 reflections with I > 2σ(I) |
Silicon monochromator | Rint = 0.08 |
ω scans | θmax = 24.6°, θmin = 1.5° |
Absorption correction: multi-scan (TWINABS; Sheldrick, 2008a) | h = −13→13 |
Tmin = 0.58, Tmax = 0.74 | k = −16→16 |
51821 measured reflections | l = 0→16 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.068 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.202 | H-atom parameters constrained |
S = 1.16 | w = 1/[σ2(Fo2) + (0.0922P)2 + 1.8862P] where P = (Fo2 + 2Fc2)/3 |
7072 reflections | (Δ/σ)max < 0.001 |
571 parameters | Δρmax = 0.58 e Å−3 |
522 restraints | Δρmin = −0.46 e Å−3 |
2C17H18FN3O3·3C2H4F2O | γ = 93.364 (2)° |
Mr = 908.84 | V = 2063.22 (11) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.9848 (4) Å | Synchrotron radiation, λ = 0.7000 Å |
b = 13.9800 (4) Å | µ = 0.13 mm−1 |
c = 13.9802 (4) Å | T = 120 K |
α = 105.6488 (18)° | 0.1 × 0.08 × 0.08 mm |
β = 90.352 (2)° |
Bruker SMART APEXII CCD area-detector diffractometer | 7072 independent reflections |
Absorption correction: multi-scan (TWINABS; Sheldrick, 2008a) | 5962 reflections with I > 2σ(I) |
Tmin = 0.58, Tmax = 0.74 | Rint = 0.08 |
51821 measured reflections |
R[F2 > 2σ(F2)] = 0.068 | 522 restraints |
wR(F2) = 0.202 | H-atom parameters constrained |
S = 1.16 | Δρmax = 0.58 e Å−3 |
7072 reflections | Δρmin = −0.46 e Å−3 |
571 parameters |
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. From TWINABS: 23224 data (5427 unique) involve domain 1 only, mean I/σ 12.7 23236 data (5429 unique) involve domain 2 only, mean I/σ 12.9 9155 data (2475 unique) involve 2 domains, mean I/σ 17.1 The quoted Rint value (0.08) comes from scaling all single and composite reflections involving domain 1. For the generation of an HKLF5 file, all observations containing domain 1 were chosen. Data were merged in TWINABS according to point group -1; single reflections that also occur in composites were omitted. |
x | y | z | Uiso*/Ueq | ||
C1A | 0.9157 (4) | 0.6677 (3) | 0.9873 (3) | 0.0288 (8) | |
H1A | 0.9913 | 0.6568 | 0.9501 | 0.035* | |
C2A | 0.8581 (5) | 0.5807 (3) | 1.0157 (3) | 0.0420 (11) | |
H2A1 | 0.8170 | 0.5932 | 1.0787 | 0.050* | |
H2A2 | 0.8986 | 0.5188 | 0.9970 | 0.050* | |
C3A | 0.8011 (4) | 0.6155 (3) | 0.9344 (3) | 0.0386 (10) | |
H3A1 | 0.7260 | 0.6493 | 0.9483 | 0.046* | |
H3A2 | 0.8077 | 0.5748 | 0.8666 | 0.046* | |
C4A | 0.8842 (3) | 0.8470 (3) | 1.0175 (3) | 0.0235 (8) | |
C5A | 0.9123 (3) | 0.7794 (3) | 1.1540 (3) | 0.0266 (8) | |
H5A | 0.9317 | 0.7250 | 1.1762 | 0.032* | |
C6A | 0.8930 (3) | 0.8662 (3) | 1.2250 (3) | 0.0249 (8) | |
C7A | 0.9057 (3) | 0.8645 (3) | 1.3323 (3) | 0.0255 (8) | |
C8A | 0.8585 (3) | 0.9511 (3) | 1.1929 (2) | 0.0219 (7) | |
C9A | 0.8628 (3) | 0.9378 (3) | 1.0849 (3) | 0.0241 (8) | |
C10A | 0.8422 (3) | 1.0192 (3) | 1.0475 (3) | 0.0237 (8) | |
H10A | 0.8266 | 1.0805 | 1.0905 | 0.028* | |
C11A | 0.8452 (3) | 1.0080 (3) | 0.9483 (3) | 0.0248 (8) | |
C12A | 0.8640 (3) | 0.9176 (3) | 0.8782 (2) | 0.0222 (7) | |
C13A | 0.9126 (3) | 0.8245 (3) | 0.7086 (2) | 0.0243 (8) | |
H13A | 0.8502 | 0.7704 | 0.6971 | 0.029* | |
H13B | 0.9841 | 0.8044 | 0.7373 | 0.029* | |
C14A | 0.9448 (3) | 0.8467 (3) | 0.6104 (3) | 0.0240 (8) | |
H14A | 1.0137 | 0.8953 | 0.6212 | 0.029* | |
H14B | 0.9687 | 0.7863 | 0.5635 | 0.029* | |
C15A | 0.7919 (3) | 0.9719 (3) | 0.6399 (2) | 0.0245 (8) | |
H15A | 0.7201 | 0.9920 | 0.6115 | 0.029* | |
H15B | 0.8525 | 1.0275 | 0.6546 | 0.029* | |
C16A | 0.7589 (3) | 0.9448 (3) | 0.7348 (3) | 0.0246 (8) | |
H16A | 0.7278 | 1.0018 | 0.7822 | 0.030* | |
H16B | 0.6958 | 0.8912 | 0.7207 | 0.030* | |
C17A | 0.8836 (3) | 0.8363 (3) | 0.9151 (3) | 0.0243 (8) | |
H17A | 0.8962 | 0.7747 | 0.8715 | 0.029* | |
F1A | 0.8334 (2) | 1.09146 (15) | 0.91582 (15) | 0.0284 (5) | |
N1A | 0.9055 (3) | 0.7661 (2) | 1.0551 (2) | 0.0251 (7) | |
N2A | 0.8682 (3) | 0.9135 (2) | 0.7771 (2) | 0.0239 (7) | |
N3A | 0.8410 (3) | 0.8854 (2) | 0.5674 (2) | 0.0228 (6) | |
H3A4 | 0.7814 | 0.8368 | 0.5481 | 0.027* | |
H3A3 | 0.8656 | 0.9037 | 0.5133 | 0.027* | |
O1A | 0.9278 (3) | 0.7830 (2) | 1.3494 (2) | 0.0404 (8) | |
O2A | 0.8963 (2) | 0.94404 (19) | 1.39869 (17) | 0.0276 (6) | |
O3A | 0.8274 (2) | 1.03187 (18) | 1.24727 (17) | 0.0253 (6) | |
C1B | 0.4484 (4) | 0.5514 (3) | 0.8104 (3) | 0.0319 (9) | |
H1B | 0.5207 | 0.5962 | 0.8113 | 0.038* | |
C2B | 0.4191 (4) | 0.5314 (3) | 0.9062 (3) | 0.0395 (10) | |
H2B1 | 0.4733 | 0.5618 | 0.9627 | 0.047* | |
H2B2 | 0.3838 | 0.4657 | 0.9049 | 0.047* | |
C3B | 0.3424 (4) | 0.5984 (3) | 0.8669 (3) | 0.0384 (10) | |
H3B1 | 0.2610 | 0.5731 | 0.8415 | 0.046* | |
H3B2 | 0.3506 | 0.6692 | 0.8993 | 0.046* | |
C4B | 0.3889 (3) | 0.5089 (3) | 0.6346 (3) | 0.0254 (8) | |
C5B | 0.4229 (3) | 0.3788 (3) | 0.7091 (3) | 0.0260 (8) | |
H5B | 0.4454 | 0.3602 | 0.7655 | 0.031* | |
C6B | 0.3937 (3) | 0.3040 (3) | 0.6251 (3) | 0.0256 (8) | |
C7B | 0.4001 (3) | 0.1985 (3) | 0.6308 (3) | 0.0245 (8) | |
C8B | 0.3571 (3) | 0.3298 (3) | 0.5358 (3) | 0.0242 (8) | |
C9B | 0.3582 (3) | 0.4370 (3) | 0.5460 (3) | 0.0254 (8) | |
C10B | 0.3259 (3) | 0.4710 (3) | 0.4636 (3) | 0.0250 (8) | |
H10B | 0.3040 | 0.4254 | 0.4033 | 0.030* | |
C11B | 0.3266 (3) | 0.5694 (3) | 0.4719 (3) | 0.0267 (8) | |
C12B | 0.3567 (3) | 0.6433 (3) | 0.5603 (3) | 0.0240 (7) | |
C13B | 0.4146 (4) | 0.8152 (3) | 0.6520 (3) | 0.0282 (8) | |
H13C | 0.4908 | 0.7916 | 0.6693 | 0.034* | |
H13D | 0.3601 | 0.8207 | 0.7073 | 0.034* | |
C14B | 0.4377 (3) | 0.9162 (3) | 0.6323 (3) | 0.0268 (8) | |
H14C | 0.4701 | 0.9638 | 0.6923 | 0.032* | |
H14D | 0.4981 | 0.9115 | 0.5811 | 0.032* | |
C15B | 0.2663 (4) | 0.8780 (3) | 0.5124 (3) | 0.0273 (8) | |
H15C | 0.3193 | 0.8700 | 0.4559 | 0.033* | |
H15D | 0.1897 | 0.9011 | 0.4952 | 0.033* | |
C16B | 0.2436 (3) | 0.7792 (3) | 0.5365 (3) | 0.0260 (8) | |
H16C | 0.1885 | 0.7868 | 0.5917 | 0.031* | |
H16D | 0.2057 | 0.7305 | 0.4795 | 0.031* | |
C17B | 0.3875 (3) | 0.6100 (3) | 0.6421 (3) | 0.0260 (8) | |
H17B | 0.4075 | 0.6561 | 0.7026 | 0.031* | |
F1B | 0.3010 (2) | 0.59818 (16) | 0.38806 (15) | 0.0318 (5) | |
N1B | 0.4220 (3) | 0.4767 (2) | 0.7173 (2) | 0.0278 (7) | |
N2B | 0.3597 (3) | 0.7443 (2) | 0.5626 (2) | 0.0261 (7) | |
N3B | 0.3242 (3) | 0.9521 (2) | 0.5999 (2) | 0.0247 (7) | |
H3B3 | 0.3418 | 1.0098 | 0.5844 | 0.030* | |
H3B4 | 0.2716 | 0.9640 | 0.6503 | 0.030* | |
O1B | 0.4321 (3) | 0.18655 (19) | 0.71462 (19) | 0.0313 (6) | |
O2B | 0.3747 (2) | 0.12815 (18) | 0.55542 (18) | 0.0277 (6) | |
O3B | 0.3268 (2) | 0.27002 (19) | 0.45403 (18) | 0.0280 (6) | |
O4A | 0.1169 (3) | 0.4141 (2) | 0.7139 (2) | 0.0451 (8) | |
H4A | 0.1199 | 0.3536 | 0.6935 | 0.068* | |
C18A | 0.0222 (5) | 0.4457 (4) | 0.6626 (4) | 0.0489 (12) | |
H18A | −0.0543 | 0.4424 | 0.6961 | 0.059* | |
H18B | 0.0129 | 0.4027 | 0.5954 | 0.059* | |
C19A | 0.0542 (4) | 0.5481 (3) | 0.6604 (4) | 0.0414 (11) | |
H19A | 0.1343 | 0.5522 | 0.6306 | 0.050* | |
F2A | −0.0329 (3) | 0.5799 (2) | 0.6068 (2) | 0.0654 (9) | |
F3A | 0.0543 (4) | 0.6118 (2) | 0.7516 (3) | 0.0825 (12) | |
O4B | 0.3352 (3) | 0.8446 (2) | 0.2558 (2) | 0.0403 (7) | |
H4B | 0.4026 | 0.8337 | 0.2747 | 0.061* | |
C18B | 0.2516 (4) | 0.7633 (3) | 0.2550 (3) | 0.0383 (10) | |
H18C | 0.1735 | 0.7881 | 0.2785 | 0.046* | |
H18D | 0.2812 | 0.7273 | 0.3000 | 0.046* | |
C19B | 0.2353 (4) | 0.6951 (3) | 0.1550 (3) | 0.0430 (11) | |
H19B | 0.2178 | 0.7332 | 0.1076 | 0.052* | |
F2B | 0.3369 (3) | 0.6442 (2) | 0.1268 (2) | 0.0624 (8) | |
F3B | 0.1414 (3) | 0.6267 (2) | 0.1530 (2) | 0.0614 (8) | |
O4C | 0.6097 (3) | 0.7792 (3) | 1.0868 (2) | 0.0481 (8) | |
H4C | 0.6047 | 0.7833 | 1.1462 | 0.072* | |
C18C | 0.5157 (4) | 0.8319 (4) | 1.0576 (3) | 0.0440 (11) | |
H18E | 0.5037 | 0.8923 | 1.1094 | 0.053* | |
H18F | 0.4397 | 0.7911 | 1.0465 | 0.053* | |
C19C | 0.5525 (4) | 0.8567 (3) | 0.9642 (3) | 0.0363 (10) | |
H19C | 0.6269 | 0.9009 | 0.9756 | 0.044* | |
F2C | 0.5685 (3) | 0.7732 (2) | 0.89043 (19) | 0.0515 (7) | |
F3C | 0.4582 (3) | 0.9011 (2) | 0.9317 (2) | 0.0612 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1A | 0.048 (2) | 0.0223 (19) | 0.0177 (18) | 0.0075 (16) | 0.0020 (16) | 0.0068 (15) |
C2A | 0.077 (3) | 0.024 (2) | 0.027 (2) | 0.001 (2) | −0.002 (2) | 0.0107 (18) |
C3A | 0.063 (3) | 0.026 (2) | 0.026 (2) | 0.0006 (19) | −0.0047 (19) | 0.0069 (17) |
C4A | 0.0321 (19) | 0.0214 (18) | 0.0194 (18) | 0.0018 (14) | −0.0003 (14) | 0.0100 (15) |
C5A | 0.038 (2) | 0.028 (2) | 0.0186 (18) | 0.0029 (16) | −0.0004 (15) | 0.0143 (16) |
C6A | 0.0349 (19) | 0.0246 (19) | 0.0164 (17) | 0.0029 (15) | 0.0012 (14) | 0.0072 (15) |
C7A | 0.038 (2) | 0.025 (2) | 0.0145 (17) | 0.0028 (16) | 0.0018 (15) | 0.0072 (15) |
C8A | 0.0328 (18) | 0.0212 (19) | 0.0120 (16) | 0.0001 (14) | 0.0015 (14) | 0.0055 (14) |
C9A | 0.0332 (19) | 0.0243 (19) | 0.0169 (17) | 0.0020 (15) | −0.0015 (14) | 0.0093 (14) |
C10A | 0.0352 (19) | 0.0184 (18) | 0.0174 (17) | 0.0026 (15) | −0.0010 (14) | 0.0046 (14) |
C11A | 0.0348 (19) | 0.0227 (19) | 0.0210 (18) | 0.0049 (15) | 0.0008 (15) | 0.0121 (15) |
C12A | 0.0295 (18) | 0.0232 (18) | 0.0162 (17) | 0.0008 (14) | 0.0009 (14) | 0.0092 (14) |
C13A | 0.0358 (19) | 0.0249 (19) | 0.0146 (17) | 0.0045 (15) | 0.0012 (14) | 0.0092 (15) |
C14A | 0.0335 (19) | 0.0245 (19) | 0.0170 (17) | 0.0057 (15) | −0.0002 (14) | 0.0099 (15) |
C15A | 0.040 (2) | 0.0199 (18) | 0.0154 (17) | 0.0032 (15) | −0.0028 (15) | 0.0080 (15) |
C16A | 0.0342 (19) | 0.027 (2) | 0.0150 (17) | 0.0044 (15) | −0.0008 (14) | 0.0093 (15) |
C17A | 0.0346 (19) | 0.0216 (19) | 0.0177 (17) | 0.0017 (15) | −0.0011 (14) | 0.0073 (15) |
F1A | 0.0510 (13) | 0.0198 (11) | 0.0181 (10) | 0.0041 (9) | −0.0005 (9) | 0.0109 (9) |
N1A | 0.0407 (17) | 0.0211 (16) | 0.0151 (15) | 0.0041 (13) | 0.0005 (12) | 0.0072 (12) |
N2A | 0.0356 (16) | 0.0231 (16) | 0.0153 (14) | 0.0063 (13) | −0.0001 (12) | 0.0082 (13) |
N3A | 0.0382 (17) | 0.0204 (16) | 0.0119 (14) | 0.0013 (13) | −0.0009 (12) | 0.0080 (12) |
O1A | 0.081 (2) | 0.0256 (15) | 0.0194 (14) | 0.0147 (14) | 0.0003 (14) | 0.0119 (12) |
O2A | 0.0469 (15) | 0.0248 (14) | 0.0140 (12) | 0.0034 (11) | 0.0014 (11) | 0.0098 (11) |
O3A | 0.0427 (14) | 0.0208 (14) | 0.0140 (12) | 0.0049 (11) | 0.0016 (10) | 0.0065 (11) |
C1B | 0.050 (2) | 0.0227 (19) | 0.0229 (19) | 0.0040 (17) | −0.0087 (17) | 0.0060 (16) |
C2B | 0.067 (3) | 0.029 (2) | 0.022 (2) | 0.007 (2) | −0.0081 (19) | 0.0064 (18) |
C3B | 0.058 (3) | 0.033 (2) | 0.025 (2) | 0.0082 (19) | −0.0037 (18) | 0.0078 (18) |
C4B | 0.0324 (19) | 0.0245 (19) | 0.0224 (18) | 0.0033 (15) | 0.0000 (15) | 0.0114 (15) |
C5B | 0.037 (2) | 0.0247 (19) | 0.0198 (18) | 0.0040 (15) | −0.0019 (15) | 0.0110 (15) |
C6B | 0.0346 (19) | 0.0217 (18) | 0.0223 (18) | 0.0040 (15) | −0.0011 (15) | 0.0084 (15) |
C7B | 0.0319 (19) | 0.0218 (19) | 0.0224 (19) | 0.0028 (14) | 0.0023 (15) | 0.0099 (16) |
C8B | 0.0309 (18) | 0.0231 (19) | 0.0212 (18) | 0.0036 (15) | 0.0024 (14) | 0.0099 (15) |
C9B | 0.0324 (19) | 0.0256 (19) | 0.0211 (18) | 0.0023 (15) | 0.0004 (15) | 0.0110 (15) |
C10B | 0.0367 (19) | 0.0238 (19) | 0.0147 (17) | 0.0011 (15) | 0.0015 (14) | 0.0059 (15) |
C11B | 0.038 (2) | 0.0271 (19) | 0.0203 (18) | 0.0049 (16) | 0.0020 (15) | 0.0143 (16) |
C12B | 0.0319 (18) | 0.0220 (18) | 0.0198 (18) | 0.0061 (14) | 0.0047 (14) | 0.0080 (15) |
C13B | 0.039 (2) | 0.0210 (19) | 0.026 (2) | 0.0050 (15) | −0.0018 (16) | 0.0084 (16) |
C14B | 0.037 (2) | 0.0183 (18) | 0.0246 (19) | 0.0035 (15) | 0.0046 (15) | 0.0041 (15) |
C15B | 0.045 (2) | 0.0183 (18) | 0.0199 (18) | 0.0042 (16) | 0.0024 (16) | 0.0069 (15) |
C16B | 0.036 (2) | 0.0210 (18) | 0.0235 (19) | 0.0038 (15) | −0.0010 (15) | 0.0097 (15) |
C17B | 0.036 (2) | 0.0194 (18) | 0.0207 (18) | 0.0013 (15) | −0.0011 (15) | 0.0027 (15) |
F1B | 0.0569 (14) | 0.0227 (11) | 0.0194 (11) | 0.0031 (10) | −0.0017 (10) | 0.0119 (9) |
N1B | 0.0401 (18) | 0.0218 (16) | 0.0236 (16) | 0.0029 (13) | −0.0057 (13) | 0.0097 (13) |
N2B | 0.0340 (17) | 0.0207 (16) | 0.0244 (16) | 0.0041 (13) | −0.0005 (13) | 0.0070 (13) |
N3B | 0.0419 (17) | 0.0183 (15) | 0.0180 (15) | 0.0052 (13) | 0.0064 (13) | 0.0110 (13) |
O1B | 0.0516 (17) | 0.0241 (14) | 0.0210 (13) | 0.0048 (12) | −0.0052 (12) | 0.0104 (11) |
O2B | 0.0454 (15) | 0.0202 (14) | 0.0202 (13) | 0.0018 (11) | −0.0003 (11) | 0.0104 (11) |
O3B | 0.0444 (15) | 0.0205 (13) | 0.0200 (13) | 0.0004 (11) | −0.0037 (11) | 0.0076 (11) |
O4A | 0.062 (2) | 0.0324 (17) | 0.0471 (19) | 0.0062 (15) | −0.0055 (15) | 0.0204 (15) |
C18A | 0.055 (3) | 0.038 (3) | 0.058 (3) | 0.007 (2) | −0.012 (2) | 0.020 (2) |
C19A | 0.046 (2) | 0.038 (3) | 0.047 (3) | 0.012 (2) | 0.001 (2) | 0.020 (2) |
F2A | 0.082 (2) | 0.0524 (18) | 0.070 (2) | 0.0205 (16) | −0.0186 (17) | 0.0274 (16) |
F3A | 0.136 (3) | 0.0416 (18) | 0.064 (2) | 0.0282 (19) | −0.030 (2) | −0.0004 (16) |
O4B | 0.0512 (18) | 0.0315 (16) | 0.0423 (18) | 0.0083 (13) | −0.0043 (14) | 0.0157 (14) |
C18B | 0.052 (2) | 0.031 (2) | 0.030 (2) | 0.0073 (19) | 0.0047 (19) | 0.0051 (19) |
C19B | 0.054 (3) | 0.040 (3) | 0.036 (2) | 0.004 (2) | 0.000 (2) | 0.011 (2) |
F2B | 0.0654 (19) | 0.0564 (19) | 0.0539 (18) | 0.0114 (15) | 0.0123 (14) | −0.0068 (15) |
F3B | 0.0675 (19) | 0.0444 (17) | 0.065 (2) | −0.0007 (14) | −0.0004 (15) | 0.0039 (15) |
O4C | 0.058 (2) | 0.060 (2) | 0.0307 (17) | 0.0122 (16) | 0.0048 (15) | 0.0194 (16) |
C18C | 0.045 (3) | 0.054 (3) | 0.034 (2) | 0.003 (2) | 0.0048 (19) | 0.013 (2) |
C19C | 0.044 (2) | 0.036 (2) | 0.027 (2) | 0.0015 (18) | −0.0041 (17) | 0.0047 (19) |
F2C | 0.0802 (19) | 0.0406 (16) | 0.0323 (14) | −0.0010 (14) | 0.0011 (13) | 0.0084 (12) |
F3C | 0.0677 (19) | 0.071 (2) | 0.0512 (17) | 0.0159 (16) | −0.0091 (14) | 0.0253 (16) |
C1A—N1A | 1.456 (5) | C5B—N1B | 1.343 (5) |
C1A—C2A | 1.487 (5) | C5B—C6B | 1.366 (5) |
C1A—C3A | 1.502 (6) | C5B—H5B | 0.930 |
C1A—H1A | 0.980 | C6B—C8B | 1.450 (5) |
C2A—C3A | 1.498 (6) | C6B—C7B | 1.505 (5) |
C2A—H2A1 | 0.970 | C7B—O2B | 1.249 (4) |
C2A—H2A2 | 0.970 | C7B—O1B | 1.278 (4) |
C3A—H3A1 | 0.970 | C8B—O3B | 1.250 (4) |
C3A—H3A2 | 0.970 | C8B—C9B | 1.466 (5) |
C4A—C9A | 1.395 (5) | C9B—C10B | 1.411 (5) |
C4A—C17A | 1.397 (5) | C10B—C11B | 1.348 (5) |
C4A—N1A | 1.400 (4) | C10B—H10B | 0.930 |
C5A—N1A | 1.346 (4) | C11B—F1B | 1.370 (4) |
C5A—C6A | 1.373 (5) | C11B—C12B | 1.404 (5) |
C5A—H5A | 0.930 | C12B—C17B | 1.392 (5) |
C6A—C8A | 1.446 (5) | C12B—N2B | 1.402 (4) |
C6A—C7A | 1.512 (5) | C13B—N2B | 1.470 (5) |
C7A—O2A | 1.251 (4) | C13B—C14B | 1.518 (5) |
C7A—O1A | 1.263 (4) | C13B—H13C | 0.970 |
C8A—O3A | 1.246 (4) | C13B—H13D | 0.970 |
C8A—C9A | 1.473 (5) | C14B—N3B | 1.483 (5) |
C9A—C10A | 1.404 (5) | C14B—H14C | 0.970 |
C10A—C11A | 1.353 (5) | C14B—H14D | 0.970 |
C10A—H10A | 0.930 | C15B—N3B | 1.485 (5) |
C11A—F1A | 1.374 (4) | C15B—C16B | 1.515 (5) |
C11A—C12A | 1.402 (5) | C15B—H15C | 0.970 |
C12A—C17A | 1.396 (5) | C15B—H15D | 0.970 |
C12A—N2A | 1.400 (4) | C16B—N2B | 1.470 (4) |
C13A—N2A | 1.462 (4) | C16B—H16C | 0.970 |
C13A—C14A | 1.526 (5) | C16B—H16D | 0.970 |
C13A—H13A | 0.970 | C17B—H17B | 0.930 |
C13A—H13B | 0.970 | N3B—H3B3 | 0.900 |
C14A—N3A | 1.481 (4) | N3B—H3B4 | 0.900 |
C14A—H14A | 0.970 | O4A—C18A | 1.417 (5) |
C14A—H14B | 0.970 | O4A—H4A | 0.820 |
C15A—N3A | 1.484 (4) | C18A—C19A | 1.463 (6) |
C15A—C16A | 1.515 (5) | C18A—H18A | 0.970 |
C15A—H15A | 0.970 | C18A—H18B | 0.970 |
C15A—H15B | 0.970 | C19A—F3A | 1.344 (6) |
C16A—N2A | 1.475 (4) | C19A—F2A | 1.376 (5) |
C16A—H16A | 0.970 | C19A—H19A | 0.980 |
C16A—H16B | 0.970 | O4B—C18B | 1.416 (5) |
C17A—H17A | 0.930 | O4B—H4B | 0.820 |
N3A—H3A4 | 0.900 | C18B—C19B | 1.467 (6) |
N3A—H3A3 | 0.900 | C18B—H18C | 0.970 |
C1B—N1B | 1.449 (5) | C18B—H18D | 0.970 |
C1B—C2B | 1.474 (5) | C19B—F3B | 1.360 (6) |
C1B—C3B | 1.494 (6) | C19B—F2B | 1.362 (5) |
C1B—H1B | 0.980 | C19B—H19B | 0.980 |
C2B—C3B | 1.502 (6) | O4C—C18C | 1.422 (6) |
C2B—H2B1 | 0.970 | O4C—H4C | 0.820 |
C2B—H2B2 | 0.970 | C18C—C19C | 1.491 (6) |
C3B—H3B1 | 0.970 | C18C—H18E | 0.970 |
C3B—H3B2 | 0.970 | C18C—H18F | 0.970 |
C4B—C17B | 1.390 (5) | C19C—F2C | 1.354 (5) |
C4B—C9B | 1.393 (5) | C19C—F3C | 1.374 (5) |
C4B—N1B | 1.402 (4) | C19C—H19C | 0.980 |
N1A—C1A—C2A | 118.0 (3) | C9B—C4B—N1B | 118.1 (3) |
N1A—C1A—C3A | 117.2 (3) | N1B—C5B—C6B | 125.7 (3) |
C2A—C1A—C3A | 60.2 (3) | N1B—C5B—H5B | 117.2 |
N1A—C1A—H1A | 116.5 | C6B—C5B—H5B | 117.2 |
C2A—C1A—H1A | 116.5 | C5B—C6B—C8B | 118.9 (3) |
C3A—C1A—H1A | 116.5 | C5B—C6B—C7B | 117.8 (3) |
C1A—C2A—C3A | 60.4 (3) | C8B—C6B—C7B | 123.3 (3) |
C1A—C2A—H2A1 | 117.7 | O2B—C7B—O1B | 123.6 (3) |
C3A—C2A—H2A1 | 117.7 | O2B—C7B—C6B | 119.7 (3) |
C1A—C2A—H2A2 | 117.7 | O1B—C7B—C6B | 116.7 (3) |
C3A—C2A—H2A2 | 117.7 | O3B—C8B—C6B | 126.3 (3) |
H2A1—C2A—H2A2 | 114.9 | O3B—C8B—C9B | 119.2 (3) |
C2A—C3A—C1A | 59.4 (3) | C6B—C8B—C9B | 114.5 (3) |
C2A—C3A—H3A1 | 117.8 | C4B—C9B—C10B | 117.2 (3) |
C1A—C3A—H3A1 | 117.8 | C4B—C9B—C8B | 123.2 (3) |
C2A—C3A—H3A2 | 117.8 | C10B—C9B—C8B | 119.6 (3) |
C1A—C3A—H3A2 | 117.8 | C11B—C10B—C9B | 120.3 (3) |
H3A1—C3A—H3A2 | 115.0 | C11B—C10B—H10B | 119.9 |
C9A—C4A—C17A | 121.3 (3) | C9B—C10B—H10B | 119.9 |
C9A—C4A—N1A | 118.1 (3) | C10B—C11B—F1B | 117.7 (3) |
C17A—C4A—N1A | 120.6 (3) | C10B—C11B—C12B | 123.6 (3) |
N1A—C5A—C6A | 125.7 (3) | F1B—C11B—C12B | 118.6 (3) |
N1A—C5A—H5A | 117.2 | C17B—C12B—N2B | 123.1 (3) |
C6A—C5A—H5A | 117.2 | C17B—C12B—C11B | 116.3 (3) |
C5A—C6A—C8A | 118.5 (3) | N2B—C12B—C11B | 120.5 (3) |
C5A—C6A—C7A | 116.8 (3) | N2B—C13B—C14B | 109.4 (3) |
C8A—C6A—C7A | 124.6 (3) | N2B—C13B—H13C | 109.8 |
O2A—C7A—O1A | 123.9 (3) | C14B—C13B—H13C | 109.8 |
O2A—C7A—C6A | 118.4 (3) | N2B—C13B—H13D | 109.8 |
O1A—C7A—C6A | 117.7 (3) | C14B—C13B—H13D | 109.8 |
O3A—C8A—C6A | 126.5 (3) | H13C—C13B—H13D | 108.3 |
O3A—C8A—C9A | 118.9 (3) | N3B—C14B—C13B | 111.4 (3) |
C6A—C8A—C9A | 114.6 (3) | N3B—C14B—H14C | 109.3 |
C4A—C9A—C10A | 118.3 (3) | C13B—C14B—H14C | 109.3 |
C4A—C9A—C8A | 122.9 (3) | N3B—C14B—H14D | 109.3 |
C10A—C9A—C8A | 118.8 (3) | C13B—C14B—H14D | 109.3 |
C11A—C10A—C9A | 119.5 (3) | H14C—C14B—H14D | 108.0 |
C11A—C10A—H10A | 120.2 | N3B—C15B—C16B | 109.5 (3) |
C9A—C10A—H10A | 120.2 | N3B—C15B—H15C | 109.8 |
C10A—C11A—F1A | 117.4 (3) | C16B—C15B—H15C | 109.8 |
C10A—C11A—C12A | 123.8 (3) | N3B—C15B—H15D | 109.8 |
F1A—C11A—C12A | 118.8 (3) | C16B—C15B—H15D | 109.8 |
C17A—C12A—N2A | 123.4 (3) | H15C—C15B—H15D | 108.2 |
C17A—C12A—C11A | 116.7 (3) | N2B—C16B—C15B | 109.8 (3) |
N2A—C12A—C11A | 119.8 (3) | N2B—C16B—H16C | 109.7 |
N2A—C13A—C14A | 109.5 (3) | C15B—C16B—H16C | 109.7 |
N2A—C13A—H13A | 109.8 | N2B—C16B—H16D | 109.7 |
C14A—C13A—H13A | 109.8 | C15B—C16B—H16D | 109.7 |
N2A—C13A—H13B | 109.8 | H16C—C16B—H16D | 108.2 |
C14A—C13A—H13B | 109.8 | C4B—C17B—C12B | 120.9 (3) |
H13A—C13A—H13B | 108.2 | C4B—C17B—H17B | 119.6 |
N3A—C14A—C13A | 111.9 (3) | C12B—C17B—H17B | 119.6 |
N3A—C14A—H14A | 109.2 | C5B—N1B—C4B | 119.6 (3) |
C13A—C14A—H14A | 109.2 | C5B—N1B—C1B | 122.3 (3) |
N3A—C14A—H14B | 109.2 | C4B—N1B—C1B | 118.0 (3) |
C13A—C14A—H14B | 109.2 | C12B—N2B—C13B | 116.6 (3) |
H14A—C14A—H14B | 107.9 | C12B—N2B—C16B | 115.1 (3) |
N3A—C15A—C16A | 110.1 (3) | C13B—N2B—C16B | 110.1 (3) |
N3A—C15A—H15A | 109.6 | C14B—N3B—C15B | 111.2 (3) |
C16A—C15A—H15A | 109.6 | C14B—N3B—H3B3 | 109.4 |
N3A—C15A—H15B | 109.6 | C15B—N3B—H3B3 | 109.4 |
C16A—C15A—H15B | 109.6 | C14B—N3B—H3B4 | 109.4 |
H15A—C15A—H15B | 108.2 | C15B—N3B—H3B4 | 109.4 |
N2A—C16A—C15A | 109.4 (3) | H3B3—N3B—H3B4 | 108.0 |
N2A—C16A—H16A | 109.8 | C18A—O4A—H4A | 109.5 |
C15A—C16A—H16A | 109.8 | O4A—C18A—C19A | 108.3 (4) |
N2A—C16A—H16B | 109.8 | O4A—C18A—H18A | 110.0 |
C15A—C16A—H16B | 109.8 | C19A—C18A—H18A | 110.0 |
H16A—C16A—H16B | 108.2 | O4A—C18A—H18B | 110.0 |
C12A—C17A—C4A | 120.3 (3) | C19A—C18A—H18B | 110.0 |
C12A—C17A—H17A | 119.9 | H18A—C18A—H18B | 108.4 |
C4A—C17A—H17A | 119.9 | F3A—C19A—F2A | 104.9 (4) |
C5A—N1A—C4A | 119.6 (3) | F3A—C19A—C18A | 111.7 (4) |
C5A—N1A—C1A | 120.4 (3) | F2A—C19A—C18A | 110.0 (4) |
C4A—N1A—C1A | 120.0 (3) | F3A—C19A—H19A | 110.0 |
C12A—N2A—C13A | 118.2 (3) | F2A—C19A—H19A | 110.0 |
C12A—N2A—C16A | 115.8 (3) | C18A—C19A—H19A | 110.0 |
C13A—N2A—C16A | 110.5 (3) | C18B—O4B—H4B | 109.5 |
C14A—N3A—C15A | 111.6 (3) | O4B—C18B—C19B | 111.5 (4) |
C14A—N3A—H3A4 | 109.3 | O4B—C18B—H18C | 109.3 |
C15A—N3A—H3A4 | 109.3 | C19B—C18B—H18C | 109.3 |
C14A—N3A—H3A3 | 109.3 | O4B—C18B—H18D | 109.3 |
C15A—N3A—H3A3 | 109.3 | C19B—C18B—H18D | 109.3 |
H3A4—N3A—H3A3 | 108.0 | H18C—C18B—H18D | 108.0 |
N1B—C1B—C2B | 121.1 (3) | F3B—C19B—F2B | 107.3 (4) |
N1B—C1B—C3B | 117.2 (4) | F3B—C19B—C18B | 110.3 (4) |
C2B—C1B—C3B | 60.8 (3) | F2B—C19B—C18B | 111.2 (4) |
N1B—C1B—H1B | 115.5 | F3B—C19B—H19B | 109.4 |
C2B—C1B—H1B | 115.5 | F2B—C19B—H19B | 109.4 |
C3B—C1B—H1B | 115.5 | C18B—C19B—H19B | 109.4 |
C1B—C2B—C3B | 60.3 (3) | C18C—O4C—H4C | 109.5 |
C1B—C2B—H2B1 | 117.7 | O4C—C18C—C19C | 108.2 (4) |
C3B—C2B—H2B1 | 117.7 | O4C—C18C—H18E | 110.1 |
C1B—C2B—H2B2 | 117.7 | C19C—C18C—H18E | 110.1 |
C3B—C2B—H2B2 | 117.7 | O4C—C18C—H18F | 110.1 |
H2B1—C2B—H2B2 | 114.9 | C19C—C18C—H18F | 110.1 |
C1B—C3B—C2B | 58.9 (3) | H18E—C18C—H18F | 108.4 |
C1B—C3B—H3B1 | 117.9 | F2C—C19C—F3C | 105.3 (3) |
C2B—C3B—H3B1 | 117.9 | F2C—C19C—C18C | 111.1 (4) |
C1B—C3B—H3B2 | 117.9 | F3C—C19C—C18C | 108.5 (4) |
C2B—C3B—H3B2 | 117.9 | F2C—C19C—H19C | 110.6 |
H3B1—C3B—H3B2 | 115.0 | F3C—C19C—H19C | 110.6 |
C17B—C4B—C9B | 121.7 (3) | C18C—C19C—H19C | 110.6 |
C17B—C4B—N1B | 120.2 (3) | ||
N1A—C1A—C2A—C3A | 107.0 (4) | N1B—C5B—C6B—C7B | −179.9 (4) |
N1A—C1A—C3A—C2A | −108.3 (4) | C5B—C6B—C7B—O2B | −179.6 (3) |
N1A—C5A—C6A—C8A | 2.1 (6) | C8B—C6B—C7B—O2B | 1.0 (6) |
N1A—C5A—C6A—C7A | −179.9 (4) | C5B—C6B—C7B—O1B | 0.3 (5) |
C5A—C6A—C7A—O2A | 175.6 (4) | C8B—C6B—C7B—O1B | −179.0 (3) |
C8A—C6A—C7A—O2A | −6.5 (6) | C5B—C6B—C8B—O3B | −179.3 (4) |
C5A—C6A—C7A—O1A | −3.0 (5) | C7B—C6B—C8B—O3B | 0.0 (6) |
C8A—C6A—C7A—O1A | 174.9 (4) | C5B—C6B—C8B—C9B | 1.2 (5) |
C5A—C6A—C8A—O3A | 173.2 (4) | C7B—C6B—C8B—C9B | −179.4 (3) |
C7A—C6A—C8A—O3A | −4.7 (6) | C17B—C4B—C9B—C10B | 0.3 (5) |
C5A—C6A—C8A—C9A | −7.3 (5) | N1B—C4B—C9B—C10B | −179.7 (3) |
C7A—C6A—C8A—C9A | 174.8 (3) | C17B—C4B—C9B—C8B | −179.1 (3) |
C17A—C4A—C9A—C10A | −1.0 (5) | N1B—C4B—C9B—C8B | 0.9 (5) |
N1A—C4A—C9A—C10A | 179.6 (3) | O3B—C8B—C9B—C4B | 179.1 (3) |
C17A—C4A—C9A—C8A | 177.8 (3) | C6B—C8B—C9B—C4B | −1.4 (5) |
N1A—C4A—C9A—C8A | −1.6 (5) | O3B—C8B—C9B—C10B | −0.4 (5) |
O3A—C8A—C9A—C4A | −173.2 (3) | C6B—C8B—C9B—C10B | 179.1 (3) |
C6A—C8A—C9A—C4A | 7.2 (5) | C4B—C9B—C10B—C11B | 0.6 (5) |
O3A—C8A—C9A—C10A | 5.5 (5) | C8B—C9B—C10B—C11B | −179.9 (3) |
C6A—C8A—C9A—C10A | −174.0 (3) | C9B—C10B—C11B—F1B | 176.5 (3) |
C4A—C9A—C10A—C11A | −0.8 (5) | C9B—C10B—C11B—C12B | −1.0 (6) |
C8A—C9A—C10A—C11A | −179.6 (3) | C10B—C11B—C12B—C17B | 0.4 (6) |
C9A—C10A—C11A—F1A | −175.4 (3) | F1B—C11B—C12B—C17B | −177.1 (3) |
C9A—C10A—C11A—C12A | 2.2 (6) | C10B—C11B—C12B—N2B | 177.7 (4) |
C10A—C11A—C12A—C17A | −1.6 (6) | F1B—C11B—C12B—N2B | 0.3 (5) |
F1A—C11A—C12A—C17A | 175.9 (3) | N2B—C13B—C14B—N3B | 56.2 (4) |
C10A—C11A—C12A—N2A | −178.7 (4) | N3B—C15B—C16B—N2B | −59.4 (4) |
F1A—C11A—C12A—N2A | −1.2 (5) | C9B—C4B—C17B—C12B | −0.9 (6) |
N2A—C13A—C14A—N3A | −55.0 (4) | N1B—C4B—C17B—C12B | 179.1 (3) |
N3A—C15A—C16A—N2A | 58.8 (4) | N2B—C12B—C17B—C4B | −176.7 (3) |
N2A—C12A—C17A—C4A | 176.7 (3) | C11B—C12B—C17B—C4B | 0.5 (5) |
C11A—C12A—C17A—C4A | −0.2 (5) | C6B—C5B—N1B—C4B | −0.1 (6) |
C9A—C4A—C17A—C12A | 1.5 (6) | C6B—C5B—N1B—C1B | 176.9 (4) |
N1A—C4A—C17A—C12A | −179.1 (3) | C17B—C4B—N1B—C5B | 180.0 (3) |
C6A—C5A—N1A—C4A | 4.1 (6) | C9B—C4B—N1B—C5B | −0.1 (5) |
C6A—C5A—N1A—C1A | −173.7 (4) | C17B—C4B—N1B—C1B | 2.8 (5) |
C9A—C4A—N1A—C5A | −4.2 (5) | C9B—C4B—N1B—C1B | −177.2 (3) |
C17A—C4A—N1A—C5A | 176.4 (3) | C2B—C1B—N1B—C5B | −30.5 (6) |
C9A—C4A—N1A—C1A | 173.7 (3) | C3B—C1B—N1B—C5B | −101.2 (4) |
C17A—C4A—N1A—C1A | −5.8 (5) | C2B—C1B—N1B—C4B | 146.5 (4) |
C2A—C1A—N1A—C5A | 37.9 (5) | C3B—C1B—N1B—C4B | 75.8 (5) |
C3A—C1A—N1A—C5A | 106.8 (4) | C17B—C12B—N2B—C13B | 8.7 (5) |
C2A—C1A—N1A—C4A | −139.9 (4) | C11B—C12B—N2B—C13B | −168.5 (3) |
C3A—C1A—N1A—C4A | −71.0 (5) | C17B—C12B—N2B—C16B | −122.4 (4) |
C17A—C12A—N2A—C13A | −9.3 (5) | C11B—C12B—N2B—C16B | 60.4 (4) |
C11A—C12A—N2A—C13A | 167.6 (3) | C14B—C13B—N2B—C12B | 166.6 (3) |
C17A—C12A—N2A—C16A | 125.2 (4) | C14B—C13B—N2B—C16B | −59.9 (4) |
C11A—C12A—N2A—C16A | −58.0 (4) | C15B—C16B—N2B—C12B | −163.5 (3) |
C14A—C13A—N2A—C12A | −163.6 (3) | C15B—C16B—N2B—C13B | 62.2 (4) |
C14A—C13A—N2A—C16A | 59.7 (4) | C13B—C14B—N3B—C15B | −54.8 (4) |
C15A—C16A—N2A—C12A | 159.8 (3) | C16B—C15B—N3B—C14B | 55.7 (4) |
C15A—C16A—N2A—C13A | −62.4 (4) | O4A—C18A—C19A—F3A | −66.8 (5) |
C13A—C14A—N3A—C15A | 53.0 (4) | O4A—C18A—C19A—F2A | 177.1 (4) |
C16A—C15A—N3A—C14A | −54.6 (4) | O4B—C18B—C19B—F3B | −170.6 (4) |
N1B—C1B—C2B—C3B | −105.9 (4) | O4B—C18B—C19B—F2B | 70.6 (5) |
N1B—C1B—C3B—C2B | 112.2 (4) | O4C—C18C—C19C—F2C | 60.4 (5) |
N1B—C5B—C6B—C8B | −0.5 (6) | O4C—C18C—C19C—F3C | 175.6 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3A—H3A3···O1Ai | 0.90 | 2.58 | 3.176 (4) | 125 |
N3A—H3A3···O2Ai | 0.90 | 1.86 | 2.758 (4) | 173 |
N3A—H3A4···O2Bii | 0.90 | 2.39 | 2.885 (4) | 114 |
N3A—H3A4···O3Bii | 0.90 | 1.85 | 2.717 (4) | 162 |
N3B—H3B3···O1Biii | 0.90 | 2.77 | 3.376 (4) | 126 |
N3B—H3B3···O2Biii | 0.90 | 1.82 | 2.724 (4) | 179 |
N3B—H3B4···O2Aiv | 0.90 | 2.50 | 2.894 (4) | 107 |
N3B—H3B4···O3Aiv | 0.90 | 1.79 | 2.687 (4) | 171 |
O4A—H4A···O1Av | 0.82 | 1.88 | 2.672 (4) | 162 |
O4B—H4B···O1Bii | 0.82 | 1.87 | 2.666 (4) | 165 |
O4C—H4C···O1Bv | 0.82 | 1.93 | 2.733 (4) | 168 |
C2A—H2A2···F3Bii | 0.97 | 2.51 | 3.207 (5) | 128 |
C14A—H14A···O2Avi | 0.97 | 2.49 | 3.350 (5) | 148 |
C14A—H14A···O3Avi | 0.97 | 2.49 | 3.274 (4) | 138 |
C16A—H16A···O4Bvii | 0.97 | 2.48 | 3.148 (5) | 126 |
C1B—H1B···F2C | 0.98 | 2.45 | 3.200 (5) | 133 |
C14B—H14D···O2Bii | 0.97 | 2.34 | 3.295 (4) | 170 |
C15B—H15D···O2Aiv | 0.97 | 2.51 | 3.131 (5) | 122 |
C18B—H18D···F1B | 0.97 | 2.46 | 3.396 (5) | 161 |
Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+1, −z+1; (iii) x, y+1, z; (iv) −x+1, −y+2, −z+2; (v) −x+1, −y+1, −z+2; (vi) −x+2, −y+2, −z+2; (vii) −x+1, −y+2, −z+1. |
3C17H18FN3O3·14.5H2O | Z = 2 |
Mr = 1255.26 | F(000) = 1334 |
Triclinic, P1 | Dx = 1.402 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 13.8760 (12) Å | Cell parameters from 6396 reflections |
b = 15.8760 (13) Å | θ = 2.4–31.4° |
c = 16.528 (2) Å | µ = 0.12 mm−1 |
α = 115.755 (7)° | T = 100 K |
β = 103.610 (7)° | Block, colourless |
γ = 102.325 (5)° | 0.30 × 0.25 × 0.20 mm |
V = 2972.8 (5) Å3 |
Bruker APEXII CCD area-detector diffractometer | 12150 independent reflections |
Radiation source: fine-focus sealed tube | 9655 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
ω scans | θmax = 26.4°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a) | h = −17→17 |
Tmin = 0.40, Tmax = 0.43 | k = −19→19 |
55842 measured reflections | l = −20→20 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0595P)2 + 1.7881P] where P = (Fo2 + 2Fc2)/3 |
12150 reflections | (Δ/σ)max < 0.001 |
907 parameters | Δρmax = 0.57 e Å−3 |
34 restraints | Δρmin = −0.42 e Å−3 |
3C17H18FN3O3·14.5H2O | γ = 102.325 (5)° |
Mr = 1255.26 | V = 2972.8 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 13.8760 (12) Å | Mo Kα radiation |
b = 15.8760 (13) Å | µ = 0.12 mm−1 |
c = 16.528 (2) Å | T = 100 K |
α = 115.755 (7)° | 0.30 × 0.25 × 0.20 mm |
β = 103.610 (7)° |
Bruker APEXII CCD area-detector diffractometer | 12150 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a) | 9655 reflections with I > 2σ(I) |
Tmin = 0.40, Tmax = 0.43 | Rint = 0.038 |
55842 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 34 restraints |
wR(F2) = 0.122 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.57 e Å−3 |
12150 reflections | Δρmin = −0.42 e Å−3 |
907 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1A | 0.01030 (13) | 0.05863 (13) | 0.75199 (12) | 0.0162 (3) | |
H1A | 0.0186 | −0.0063 | 0.7203 | 0.019* | |
C2A | −0.00057 (14) | 0.08955 (14) | 0.84785 (13) | 0.0210 (4) | |
H2A1 | −0.0004 | 0.0436 | 0.8718 | 0.025* | |
H2A2 | −0.0460 | 0.1278 | 0.8642 | 0.025* | |
C3A | 0.10167 (13) | 0.13991 (13) | 0.84351 (13) | 0.0187 (4) | |
H3A1 | 0.1175 | 0.2083 | 0.8571 | 0.022* | |
H3A2 | 0.1631 | 0.1241 | 0.8647 | 0.022* | |
C4A | −0.00372 (13) | 0.11147 (12) | 0.63089 (12) | 0.0149 (3) | |
C5A | −0.15004 (13) | 0.07864 (13) | 0.67699 (13) | 0.0165 (3) | |
H5A | −0.1803 | 0.0561 | 0.7118 | 0.020* | |
C6A | −0.21164 (13) | 0.10248 (13) | 0.61823 (12) | 0.0166 (3) | |
C7A | −0.32080 (13) | 0.09554 (13) | 0.62078 (13) | 0.0185 (4) | |
C8A | −0.17049 (13) | 0.13364 (12) | 0.55932 (12) | 0.0154 (3) | |
C9A | −0.06323 (13) | 0.13288 (12) | 0.56604 (12) | 0.0155 (3) | |
C10A | −0.01854 (13) | 0.14943 (13) | 0.50339 (12) | 0.0161 (3) | |
H10A | −0.0565 | 0.1621 | 0.4583 | 0.019* | |
C11A | 0.08030 (13) | 0.14676 (12) | 0.50921 (12) | 0.0155 (3) | |
C12A | 0.14544 (13) | 0.13332 (12) | 0.57909 (12) | 0.0146 (3) | |
C13A | 0.30262 (13) | 0.11202 (13) | 0.65625 (12) | 0.0164 (3) | |
H13A | 0.2564 | 0.0512 | 0.6479 | 0.020* | |
H13B | 0.3178 | 0.1665 | 0.7206 | 0.020* | |
C14A | 0.40542 (13) | 0.09951 (13) | 0.64716 (13) | 0.0174 (3) | |
H14A | 0.4417 | 0.0897 | 0.6984 | 0.021* | |
H14B | 0.3896 | 0.0404 | 0.5856 | 0.021* | |
C15A | 0.42007 (13) | 0.20740 (14) | 0.57800 (13) | 0.0187 (4) | |
H15A | 0.4035 | 0.1510 | 0.5143 | 0.022* | |
H15B | 0.4659 | 0.2669 | 0.5838 | 0.022* | |
C16A | 0.31815 (13) | 0.22165 (13) | 0.58904 (13) | 0.0170 (3) | |
H16A | 0.3353 | 0.2810 | 0.6508 | 0.020* | |
H16B | 0.2813 | 0.2317 | 0.5382 | 0.020* | |
C17A | 0.10022 (13) | 0.11484 (13) | 0.63909 (12) | 0.0157 (3) | |
H17A | 0.1396 | 0.1045 | 0.6856 | 0.019* | |
F1A | 0.11574 (8) | 0.15200 (8) | 0.44057 (7) | 0.0193 (2) | |
N1A | −0.04887 (11) | 0.08558 (11) | 0.68779 (10) | 0.0152 (3) | |
N2A | 0.24798 (11) | 0.13337 (11) | 0.58360 (10) | 0.0152 (3) | |
N3A | 0.47622 (11) | 0.18885 (11) | 0.65348 (11) | 0.0168 (3) | |
H3A3 | 0.4957 | 0.2429 | 0.7125 | 0.020* | |
H3A4 | 0.5354 | 0.1786 | 0.6452 | 0.020* | |
O1A | −0.36156 (10) | 0.03730 (10) | 0.64688 (10) | 0.0256 (3) | |
O2A | −0.36312 (10) | 0.14924 (11) | 0.59960 (10) | 0.0244 (3) | |
O3A | −0.22068 (9) | 0.15653 (9) | 0.50312 (9) | 0.0194 (3) | |
C1B | 0.29467 (14) | 0.23071 (13) | 0.30397 (12) | 0.0182 (4) | |
H1C | 0.3280 | 0.2588 | 0.2707 | 0.022* | |
C2B | 0.20504 (15) | 0.13171 (13) | 0.24003 (13) | 0.0223 (4) | |
H2C1 | 0.1845 | 0.1023 | 0.1706 | 0.027* | |
H2D2 | 0.1469 | 0.1188 | 0.2613 | 0.027* | |
C3B | 0.31166 (15) | 0.13773 (14) | 0.29628 (14) | 0.0247 (4) | |
H3C1 | 0.3175 | 0.1286 | 0.3513 | 0.030* | |
H3D2 | 0.3551 | 0.1120 | 0.2606 | 0.030* | |
C4B | 0.38410 (13) | 0.36527 (12) | 0.47548 (12) | 0.0149 (3) | |
C5B | 0.19722 (13) | 0.31214 (13) | 0.39923 (13) | 0.0167 (3) | |
H5C | 0.1369 | 0.2728 | 0.3427 | 0.020* | |
C6B | 0.18425 (13) | 0.37441 (13) | 0.48112 (13) | 0.0166 (3) | |
C7B | 0.07127 (14) | 0.36530 (13) | 0.47227 (13) | 0.0193 (4) | |
C8B | 0.27616 (13) | 0.44012 (13) | 0.57029 (12) | 0.0159 (3) | |
C9B | 0.37795 (13) | 0.43309 (13) | 0.56186 (12) | 0.0155 (3) | |
C10B | 0.47369 (14) | 0.49694 (13) | 0.64258 (12) | 0.0166 (3) | |
H10C | 0.4728 | 0.5432 | 0.7010 | 0.020* | |
C11B | 0.56765 (13) | 0.49026 (13) | 0.63440 (12) | 0.0164 (3) | |
C12B | 0.57591 (13) | 0.41920 (13) | 0.55003 (12) | 0.0152 (3) | |
C13B | 0.67626 (13) | 0.35036 (13) | 0.45292 (12) | 0.0168 (3) | |
H13C | 0.6388 | 0.3652 | 0.4064 | 0.020* | |
H13D | 0.6394 | 0.2809 | 0.4320 | 0.020* | |
C14B | 0.78931 (14) | 0.36560 (14) | 0.45669 (13) | 0.0187 (4) | |
H14C | 0.7880 | 0.3197 | 0.3937 | 0.022* | |
H14D | 0.8239 | 0.4334 | 0.4719 | 0.022* | |
C15B | 0.84785 (14) | 0.41153 (15) | 0.62718 (13) | 0.0217 (4) | |
H15C | 0.8844 | 0.4817 | 0.6503 | 0.026* | |
H15D | 0.8842 | 0.3954 | 0.6732 | 0.026* | |
C16B | 0.73346 (14) | 0.39399 (14) | 0.62038 (13) | 0.0188 (4) | |
H16C | 0.6981 | 0.3248 | 0.6012 | 0.023* | |
H16D | 0.7323 | 0.4368 | 0.6833 | 0.023* | |
C17B | 0.48173 (13) | 0.35762 (12) | 0.46986 (12) | 0.0151 (3) | |
H17C | 0.4833 | 0.3109 | 0.4120 | 0.018* | |
F1B | 0.65970 (8) | 0.55830 (8) | 0.71088 (7) | 0.0204 (2) | |
N1B | 0.29006 (11) | 0.30310 (11) | 0.39370 (10) | 0.0162 (3) | |
N2B | 0.67632 (11) | 0.41602 (11) | 0.54880 (10) | 0.0158 (3) | |
N3B | 0.85125 (11) | 0.34822 (11) | 0.53093 (11) | 0.0188 (3) | |
H3B3 | 0.8242 | 0.2832 | 0.5128 | 0.023* | |
H3B4 | 0.9192 | 0.3626 | 0.5351 | 0.023* | |
O1B | 0.00013 (10) | 0.31583 (10) | 0.38875 (10) | 0.0269 (3) | |
O2B | 0.05349 (10) | 0.40641 (10) | 0.54905 (10) | 0.0247 (3) | |
O3B | 0.27442 (10) | 0.50037 (9) | 0.64887 (9) | 0.0203 (3) | |
C1C | 0.10738 (14) | 0.31041 (13) | 0.07593 (13) | 0.0183 (4) | |
H1E | 0.0437 | 0.2727 | 0.0164 | 0.022* | |
C2C | 0.16026 (14) | 0.24825 (14) | 0.10174 (13) | 0.0214 (4) | |
H2E1 | 0.2371 | 0.2760 | 0.1335 | 0.026* | |
H2F2 | 0.1302 | 0.1762 | 0.0579 | 0.026* | |
C3C | 0.09685 (15) | 0.29607 (14) | 0.15790 (14) | 0.0221 (4) | |
H3E1 | 0.0287 | 0.2528 | 0.1476 | 0.027* | |
H3F2 | 0.1355 | 0.3526 | 0.2233 | 0.027* | |
C4C | 0.12151 (13) | 0.48096 (13) | 0.11331 (12) | 0.0166 (3) | |
C5C | 0.27096 (13) | 0.43313 (13) | 0.10391 (12) | 0.0170 (3) | |
H5E | 0.2996 | 0.3830 | 0.0904 | 0.020* | |
C6C | 0.33560 (13) | 0.52667 (13) | 0.12925 (12) | 0.0174 (4) | |
C7C | 0.45042 (14) | 0.54273 (14) | 0.14200 (12) | 0.0187 (4) | |
C8C | 0.29293 (14) | 0.60469 (13) | 0.14454 (12) | 0.0178 (4) | |
C9C | 0.18149 (14) | 0.57680 (13) | 0.13538 (12) | 0.0179 (4) | |
C10C | 0.13191 (14) | 0.64792 (14) | 0.14996 (13) | 0.0208 (4) | |
H10E | 0.1689 | 0.7116 | 0.1635 | 0.025* | |
C11C | 0.02942 (15) | 0.62282 (14) | 0.14418 (13) | 0.0218 (4) | |
C12C | −0.03129 (14) | 0.52869 (14) | 0.12660 (12) | 0.0193 (4) | |
C13C | −0.20246 (14) | 0.40775 (15) | 0.08716 (14) | 0.0250 (4) | |
H13E | −0.1788 | 0.3868 | 0.1330 | 0.030* | |
H13F | −0.1968 | 0.3639 | 0.0269 | 0.030* | |
C14C | −0.31720 (15) | 0.40022 (16) | 0.07001 (14) | 0.0299 (5) | |
H14E | −0.3422 | 0.4161 | 0.0204 | 0.036* | |
H14F | −0.3612 | 0.3320 | 0.0470 | 0.036* | |
C15C | −0.25400 (16) | 0.57458 (15) | 0.20396 (15) | 0.0254 (4) | |
H15E | −0.2581 | 0.6169 | 0.2656 | 0.031* | |
H15F | −0.2750 | 0.6002 | 0.1616 | 0.031* | |
C16C | −0.14139 (15) | 0.57851 (14) | 0.21914 (13) | 0.0224 (4) | |
H16E | −0.0945 | 0.6468 | 0.2459 | 0.027* | |
H16F | −0.1185 | 0.5571 | 0.2647 | 0.027* | |
C17C | 0.01608 (14) | 0.45761 (13) | 0.10949 (12) | 0.0180 (4) | |
H17E | −0.0219 | 0.3939 | 0.0953 | 0.022* | |
F1C | −0.01800 (9) | 0.69140 (8) | 0.15369 (9) | 0.0294 (3) | |
N1C | 0.16929 (11) | 0.40926 (11) | 0.09739 (10) | 0.0163 (3) | |
N2C | −0.13518 (12) | 0.51201 (12) | 0.12542 (11) | 0.0210 (3) | |
N3C | −0.32810 (12) | 0.47000 (12) | 0.16036 (11) | 0.0234 (3) | |
H3C4 | −0.3954 | 0.4685 | 0.1468 | 0.028* | |
H3C3 | −0.3144 | 0.4495 | 0.2033 | 0.028* | |
O1C | 0.47208 (10) | 0.46445 (10) | 0.10160 (10) | 0.0244 (3) | |
O2C | 0.51768 (10) | 0.62985 (9) | 0.19216 (9) | 0.0225 (3) | |
O3C | 0.34399 (10) | 0.69030 (9) | 0.16331 (10) | 0.0236 (3) | |
OW1A | 0.6940 (3) | 0.1254 (3) | 1.0564 (2) | 0.0384 (7) | 0.50 |
OW1B | 0.6126 (4) | 0.0704 (3) | 1.0436 (3) | 0.0669 (12) | 0.50 |
OW2A | 0.3200 (2) | 0.0970 (2) | 0.04907 (19) | 0.0393 (6) | 0.60 |
OW2B | 0.2159 (2) | −0.0042 (2) | −0.0927 (2) | 0.0223 (7) | 0.40 |
OW3A | 0.5083 (2) | 0.2178 (2) | 0.2245 (2) | 0.0319 (7) | 0.50 |
OW3B | 0.4730 (4) | 0.2825 (4) | 0.1750 (3) | 0.0823 (16) | 0.50 |
OW4A | 0.2248 (2) | 0.97205 (19) | 0.74736 (18) | 0.0330 (6) | 0.60 |
OW4B | 0.1614 (3) | 0.8795 (3) | 0.7071 (2) | 0.0295 (8) | 0.40 |
OW5A | 0.6790 (2) | 0.2961 (2) | 0.1828 (2) | 0.0257 (6) | 0.50 |
OW5B | 0.6683 (3) | 0.2485 (3) | 0.2086 (2) | 0.0454 (8) | 0.50 |
OW6A | 0.8952 (3) | 0.0356 (3) | 0.0276 (2) | 0.0237 (7) | 0.50 |
OW6B | 0.9370 (3) | 0.0326 (3) | 0.0136 (3) | 0.0265 (7) | 0.50 |
OW7A | 0.3738 (3) | 0.1689 (3) | 0.9555 (3) | 0.0413 (9) | 0.60 |
OW7B | 0.3657 (5) | 0.1445 (4) | 0.9120 (3) | 0.0257 (12) | 0.40 |
OW8 | 0.33039 (15) | 0.85648 (12) | 0.16362 (12) | 0.0434 (4) | |
H81 | 0.347 (2) | 0.8994 (17) | 0.2238 (9) | 0.065* | |
H82 | 0.335 (2) | 0.8006 (13) | 0.157 (2) | 0.065* | |
OW9 | 0.45285 (10) | 0.88062 (10) | 0.58803 (10) | 0.0245 (3) | |
H91 | 0.4050 (14) | 0.8686 (18) | 0.5370 (12) | 0.037* | |
H92 | 0.5089 (12) | 0.9297 (13) | 0.6042 (16) | 0.037* | |
OW10 | 0.88366 (12) | 0.39539 (11) | 0.29624 (10) | 0.0312 (3) | |
H101 | 0.9215 (18) | 0.3725 (18) | 0.3245 (17) | 0.047* | |
H102 | 0.887 (2) | 0.4539 (11) | 0.3383 (15) | 0.047* | |
OW11 | 0.37127 (11) | 0.31620 (10) | −0.08836 (10) | 0.0278 (3) | |
H111 | 0.4046 (18) | 0.3286 (18) | −0.1224 (15) | 0.042* | |
H112 | 0.4023 (18) | 0.3647 (14) | −0.0296 (9) | 0.042* | |
OW12 | 0.62077 (15) | 0.10562 (12) | 0.27024 (12) | 0.0409 (4) | |
H121 | 0.601 (2) | 0.111 (2) | 0.3170 (16) | 0.061* | |
H122 | 0.623 (2) | 0.1469 (18) | 0.251 (2) | 0.061* | |
OW13 | 0.85309 (12) | 0.17866 (13) | −0.01946 (13) | 0.0421 (4) | |
H131 | 0.8028 (17) | 0.165 (2) | −0.0700 (14) | 0.063* | |
H132 | 0.825 (2) | 0.156 (2) | 0.0111 (19) | 0.063* | |
OW14 | 0.51312 (19) | 0.07464 (14) | 0.89016 (13) | 0.0582 (5) | |
H141 | 0.548 (2) | 0.116 (2) | 0.9534 (8) | 0.087* | |
H142 | 0.548 (2) | 0.093 (3) | 0.860 (2) | 0.087* | |
OW15 | 0.93634 (19) | 0.12971 (18) | 0.22207 (17) | 0.0181 (5) | 0.50 |
H151 | 0.882 (2) | 0.095 (2) | 0.224 (3) | 0.027* | 0.50 |
H152 | 0.961 (3) | 0.1890 (11) | 0.265 (2) | 0.027* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1A | 0.0143 (8) | 0.0174 (8) | 0.0199 (9) | 0.0075 (7) | 0.0071 (7) | 0.0109 (7) |
C2A | 0.0192 (9) | 0.0233 (9) | 0.0202 (9) | 0.0064 (7) | 0.0080 (7) | 0.0112 (8) |
C3A | 0.0149 (8) | 0.0190 (9) | 0.0209 (9) | 0.0057 (7) | 0.0043 (7) | 0.0105 (7) |
C4A | 0.0135 (8) | 0.0134 (8) | 0.0176 (8) | 0.0048 (6) | 0.0068 (6) | 0.0074 (7) |
C5A | 0.0121 (8) | 0.0151 (8) | 0.0212 (9) | 0.0041 (6) | 0.0073 (7) | 0.0083 (7) |
C6A | 0.0128 (8) | 0.0147 (8) | 0.0202 (8) | 0.0054 (6) | 0.0060 (7) | 0.0071 (7) |
C7A | 0.0129 (8) | 0.0189 (9) | 0.0206 (9) | 0.0053 (7) | 0.0057 (7) | 0.0081 (7) |
C8A | 0.0129 (8) | 0.0119 (8) | 0.0174 (8) | 0.0055 (6) | 0.0036 (6) | 0.0049 (7) |
C9A | 0.0119 (8) | 0.0134 (8) | 0.0189 (8) | 0.0045 (6) | 0.0045 (6) | 0.0070 (7) |
C10A | 0.0139 (8) | 0.0155 (8) | 0.0175 (8) | 0.0061 (7) | 0.0035 (6) | 0.0080 (7) |
C11A | 0.0168 (8) | 0.0134 (8) | 0.0152 (8) | 0.0049 (6) | 0.0070 (6) | 0.0062 (7) |
C12A | 0.0129 (8) | 0.0121 (8) | 0.0170 (8) | 0.0056 (6) | 0.0056 (6) | 0.0055 (7) |
C13A | 0.0129 (8) | 0.0192 (8) | 0.0195 (8) | 0.0071 (7) | 0.0066 (7) | 0.0110 (7) |
C14A | 0.0150 (8) | 0.0181 (8) | 0.0216 (9) | 0.0080 (7) | 0.0073 (7) | 0.0111 (7) |
C15A | 0.0145 (8) | 0.0231 (9) | 0.0226 (9) | 0.0079 (7) | 0.0084 (7) | 0.0138 (8) |
C16A | 0.0142 (8) | 0.0171 (8) | 0.0223 (9) | 0.0072 (7) | 0.0072 (7) | 0.0112 (7) |
C17A | 0.0138 (8) | 0.0165 (8) | 0.0185 (8) | 0.0073 (7) | 0.0057 (7) | 0.0096 (7) |
F1A | 0.0166 (5) | 0.0259 (5) | 0.0185 (5) | 0.0085 (4) | 0.0083 (4) | 0.0128 (4) |
N1A | 0.0134 (7) | 0.0156 (7) | 0.0182 (7) | 0.0061 (6) | 0.0061 (6) | 0.0095 (6) |
N2A | 0.0117 (7) | 0.0172 (7) | 0.0191 (7) | 0.0066 (6) | 0.0066 (6) | 0.0101 (6) |
N3A | 0.0127 (7) | 0.0185 (7) | 0.0196 (7) | 0.0068 (6) | 0.0071 (6) | 0.0089 (6) |
O1A | 0.0163 (6) | 0.0268 (7) | 0.0387 (8) | 0.0071 (5) | 0.0127 (6) | 0.0200 (6) |
O2A | 0.0184 (6) | 0.0354 (8) | 0.0327 (7) | 0.0177 (6) | 0.0144 (6) | 0.0222 (6) |
O3A | 0.0141 (6) | 0.0219 (6) | 0.0241 (6) | 0.0081 (5) | 0.0061 (5) | 0.0131 (5) |
C1B | 0.0177 (8) | 0.0193 (9) | 0.0145 (8) | 0.0067 (7) | 0.0048 (7) | 0.0067 (7) |
C2B | 0.0215 (9) | 0.0178 (9) | 0.0198 (9) | 0.0054 (7) | 0.0046 (7) | 0.0057 (7) |
C3B | 0.0272 (10) | 0.0202 (9) | 0.0216 (9) | 0.0111 (8) | 0.0052 (8) | 0.0074 (8) |
C4B | 0.0151 (8) | 0.0140 (8) | 0.0170 (8) | 0.0049 (6) | 0.0048 (7) | 0.0097 (7) |
C5B | 0.0146 (8) | 0.0163 (8) | 0.0189 (8) | 0.0052 (7) | 0.0039 (7) | 0.0101 (7) |
C6B | 0.0149 (8) | 0.0168 (8) | 0.0213 (9) | 0.0070 (7) | 0.0063 (7) | 0.0119 (7) |
C7B | 0.0172 (8) | 0.0174 (9) | 0.0255 (9) | 0.0083 (7) | 0.0076 (7) | 0.0119 (8) |
C8B | 0.0172 (8) | 0.0155 (8) | 0.0194 (9) | 0.0078 (7) | 0.0076 (7) | 0.0111 (7) |
C9B | 0.0157 (8) | 0.0153 (8) | 0.0181 (8) | 0.0063 (7) | 0.0063 (7) | 0.0102 (7) |
C10B | 0.0189 (8) | 0.0157 (8) | 0.0165 (8) | 0.0074 (7) | 0.0078 (7) | 0.0083 (7) |
C11B | 0.0149 (8) | 0.0152 (8) | 0.0157 (8) | 0.0034 (7) | 0.0019 (6) | 0.0079 (7) |
C12B | 0.0149 (8) | 0.0161 (8) | 0.0179 (8) | 0.0062 (7) | 0.0072 (7) | 0.0106 (7) |
C13B | 0.0157 (8) | 0.0175 (8) | 0.0179 (8) | 0.0060 (7) | 0.0073 (7) | 0.0091 (7) |
C14B | 0.0173 (8) | 0.0201 (9) | 0.0229 (9) | 0.0083 (7) | 0.0099 (7) | 0.0124 (7) |
C15B | 0.0174 (9) | 0.0263 (10) | 0.0205 (9) | 0.0105 (7) | 0.0060 (7) | 0.0106 (8) |
C16B | 0.0174 (8) | 0.0228 (9) | 0.0194 (9) | 0.0096 (7) | 0.0077 (7) | 0.0119 (7) |
C17B | 0.0161 (8) | 0.0147 (8) | 0.0163 (8) | 0.0061 (7) | 0.0070 (7) | 0.0086 (7) |
F1B | 0.0141 (5) | 0.0195 (5) | 0.0175 (5) | 0.0036 (4) | 0.0022 (4) | 0.0044 (4) |
N1B | 0.0146 (7) | 0.0161 (7) | 0.0161 (7) | 0.0056 (6) | 0.0049 (6) | 0.0071 (6) |
N2B | 0.0140 (7) | 0.0178 (7) | 0.0173 (7) | 0.0074 (6) | 0.0063 (6) | 0.0093 (6) |
N3B | 0.0148 (7) | 0.0192 (7) | 0.0240 (8) | 0.0082 (6) | 0.0086 (6) | 0.0108 (6) |
O1B | 0.0168 (6) | 0.0294 (7) | 0.0252 (7) | 0.0116 (6) | 0.0025 (5) | 0.0076 (6) |
O2B | 0.0159 (6) | 0.0274 (7) | 0.0263 (7) | 0.0085 (5) | 0.0098 (5) | 0.0089 (6) |
O3B | 0.0182 (6) | 0.0227 (7) | 0.0185 (6) | 0.0093 (5) | 0.0076 (5) | 0.0080 (5) |
C1C | 0.0165 (8) | 0.0145 (8) | 0.0184 (8) | 0.0049 (7) | 0.0038 (7) | 0.0058 (7) |
C2C | 0.0199 (9) | 0.0164 (9) | 0.0243 (9) | 0.0068 (7) | 0.0040 (7) | 0.0094 (7) |
C3C | 0.0211 (9) | 0.0193 (9) | 0.0231 (9) | 0.0054 (7) | 0.0067 (7) | 0.0102 (8) |
C4C | 0.0180 (8) | 0.0177 (8) | 0.0139 (8) | 0.0095 (7) | 0.0044 (7) | 0.0073 (7) |
C5C | 0.0162 (8) | 0.0196 (9) | 0.0150 (8) | 0.0092 (7) | 0.0047 (7) | 0.0080 (7) |
C6C | 0.0159 (8) | 0.0193 (9) | 0.0156 (8) | 0.0068 (7) | 0.0045 (7) | 0.0082 (7) |
C7C | 0.0185 (8) | 0.0224 (9) | 0.0150 (8) | 0.0072 (7) | 0.0066 (7) | 0.0092 (7) |
C8C | 0.0176 (8) | 0.0184 (9) | 0.0141 (8) | 0.0050 (7) | 0.0021 (7) | 0.0081 (7) |
C9C | 0.0184 (8) | 0.0195 (9) | 0.0153 (8) | 0.0086 (7) | 0.0043 (7) | 0.0086 (7) |
C10C | 0.0221 (9) | 0.0177 (9) | 0.0208 (9) | 0.0090 (7) | 0.0049 (7) | 0.0091 (7) |
C11C | 0.0259 (9) | 0.0212 (9) | 0.0215 (9) | 0.0158 (8) | 0.0079 (7) | 0.0106 (8) |
C12C | 0.0187 (8) | 0.0229 (9) | 0.0144 (8) | 0.0103 (7) | 0.0039 (7) | 0.0079 (7) |
C13C | 0.0166 (9) | 0.0254 (10) | 0.0228 (9) | 0.0103 (8) | 0.0034 (7) | 0.0049 (8) |
C14C | 0.0188 (9) | 0.0340 (11) | 0.0238 (10) | 0.0117 (8) | 0.0042 (8) | 0.0050 (9) |
C15C | 0.0303 (10) | 0.0260 (10) | 0.0291 (10) | 0.0178 (8) | 0.0169 (8) | 0.0150 (8) |
C16C | 0.0246 (9) | 0.0220 (9) | 0.0202 (9) | 0.0120 (8) | 0.0089 (7) | 0.0085 (8) |
C17C | 0.0172 (8) | 0.0177 (8) | 0.0170 (8) | 0.0071 (7) | 0.0047 (7) | 0.0076 (7) |
F1C | 0.0303 (6) | 0.0266 (6) | 0.0427 (7) | 0.0212 (5) | 0.0169 (5) | 0.0204 (5) |
N1C | 0.0149 (7) | 0.0154 (7) | 0.0171 (7) | 0.0069 (6) | 0.0046 (6) | 0.0071 (6) |
N2C | 0.0185 (7) | 0.0237 (8) | 0.0193 (7) | 0.0118 (6) | 0.0069 (6) | 0.0079 (6) |
N3C | 0.0197 (8) | 0.0316 (9) | 0.0229 (8) | 0.0149 (7) | 0.0077 (6) | 0.0147 (7) |
O1C | 0.0187 (6) | 0.0216 (7) | 0.0273 (7) | 0.0087 (5) | 0.0097 (5) | 0.0067 (6) |
O2C | 0.0169 (6) | 0.0200 (7) | 0.0240 (7) | 0.0042 (5) | 0.0065 (5) | 0.0076 (6) |
O3C | 0.0218 (6) | 0.0180 (6) | 0.0282 (7) | 0.0056 (5) | 0.0053 (5) | 0.0122 (6) |
OW1A | 0.050 (2) | 0.0358 (18) | 0.0405 (18) | 0.0213 (16) | 0.0268 (16) | 0.0207 (15) |
OW1B | 0.082 (3) | 0.067 (3) | 0.042 (2) | 0.039 (3) | 0.014 (2) | 0.018 (2) |
OW2A | 0.0341 (14) | 0.0446 (16) | 0.0382 (15) | 0.0130 (12) | 0.0123 (11) | 0.0216 (13) |
OW2B | 0.0217 (16) | 0.0223 (16) | 0.0280 (17) | 0.0101 (13) | 0.0123 (14) | 0.0146 (14) |
OW3A | 0.0267 (14) | 0.0359 (16) | 0.0224 (14) | 0.0036 (12) | 0.0099 (12) | 0.0094 (12) |
OW3B | 0.085 (3) | 0.068 (3) | 0.054 (3) | 0.050 (3) | 0.007 (2) | −0.001 (2) |
OW4A | 0.0333 (13) | 0.0323 (13) | 0.0374 (14) | 0.0109 (11) | 0.0165 (11) | 0.0197 (11) |
OW4B | 0.0233 (17) | 0.037 (2) | 0.0246 (18) | 0.0037 (15) | 0.0057 (14) | 0.0178 (16) |
OW5A | 0.0289 (15) | 0.0242 (14) | 0.0308 (15) | 0.0075 (12) | 0.0152 (12) | 0.0185 (13) |
OW5B | 0.0363 (18) | 0.044 (2) | 0.0357 (18) | 0.0080 (16) | 0.0062 (14) | 0.0112 (17) |
OW6A | 0.0188 (17) | 0.0277 (16) | 0.0255 (16) | 0.0103 (14) | 0.0095 (13) | 0.0128 (13) |
OW6B | 0.0272 (19) | 0.0295 (16) | 0.0300 (17) | 0.0131 (16) | 0.0167 (15) | 0.0165 (14) |
OW7A | 0.0261 (16) | 0.032 (2) | 0.074 (3) | 0.0125 (15) | 0.020 (2) | 0.032 (2) |
OW7B | 0.040 (2) | 0.018 (2) | 0.015 (2) | 0.0085 (18) | 0.017 (2) | 0.0027 (19) |
OW8 | 0.0617 (11) | 0.0246 (8) | 0.0324 (8) | 0.0128 (8) | −0.0011 (8) | 0.0159 (7) |
OW9 | 0.0197 (7) | 0.0246 (7) | 0.0289 (7) | 0.0057 (6) | 0.0064 (6) | 0.0158 (6) |
OW10 | 0.0415 (9) | 0.0324 (8) | 0.0265 (8) | 0.0219 (7) | 0.0149 (7) | 0.0157 (6) |
OW11 | 0.0333 (8) | 0.0222 (7) | 0.0231 (7) | 0.0059 (6) | 0.0104 (6) | 0.0097 (6) |
OW12 | 0.0581 (11) | 0.0306 (8) | 0.0416 (9) | 0.0172 (8) | 0.0319 (8) | 0.0174 (7) |
OW13 | 0.0231 (8) | 0.0475 (10) | 0.0426 (10) | 0.0131 (7) | 0.0076 (7) | 0.0144 (8) |
OW14 | 0.0996 (17) | 0.0378 (10) | 0.0370 (10) | 0.0229 (10) | 0.0308 (11) | 0.0171 (8) |
OW15 | 0.0155 (12) | 0.0135 (12) | 0.0188 (12) | 0.0029 (10) | 0.0080 (10) | 0.0032 (10) |
C1A—N1A | 1.455 (2) | C13B—H13D | 0.970 |
C1A—C2A | 1.497 (2) | C14B—N3B | 1.490 (2) |
C1A—C3A | 1.505 (2) | C14B—H14C | 0.970 |
C1A—H1A | 0.980 | C14B—H14D | 0.970 |
C2A—C3A | 1.507 (2) | C15B—N3B | 1.486 (2) |
C2A—H2A1 | 0.970 | C15B—C16B | 1.520 (2) |
C2A—H2A2 | 0.970 | C15B—H15C | 0.970 |
C3A—H3A1 | 0.970 | C15B—H15D | 0.970 |
C3A—H3A2 | 0.970 | C16B—N2B | 1.479 (2) |
C4A—N1A | 1.396 (2) | C16B—H16C | 0.970 |
C4A—C9A | 1.402 (2) | C16B—H16D | 0.970 |
C4A—C17A | 1.404 (2) | C17B—H17C | 0.930 |
C5A—N1A | 1.347 (2) | N3B—H3B3 | 0.900 |
C5A—C6A | 1.372 (2) | N3B—H3B4 | 0.900 |
C5A—H5A | 0.930 | C1C—N1C | 1.457 (2) |
C6A—C8A | 1.442 (2) | C1C—C2C | 1.491 (3) |
C6A—C7A | 1.507 (2) | C1C—C3C | 1.502 (3) |
C7A—O2A | 1.253 (2) | C1C—H1E | 0.980 |
C7A—O1A | 1.265 (2) | C2C—C3C | 1.506 (3) |
C8A—O3A | 1.256 (2) | C2C—H2E1 | 0.970 |
C8A—C9A | 1.469 (2) | C2C—H2F2 | 0.970 |
C9A—C10A | 1.412 (2) | C3C—H3E1 | 0.970 |
C10A—C11A | 1.363 (2) | C3C—H3F2 | 0.970 |
C10A—H10A | 0.930 | C4C—N1C | 1.396 (2) |
C11A—F1A | 1.3649 (19) | C4C—C9C | 1.405 (3) |
C11A—C12A | 1.415 (2) | C4C—C17C | 1.409 (2) |
C12A—C17A | 1.389 (2) | C5C—N1C | 1.345 (2) |
C12A—N2A | 1.407 (2) | C5C—C6C | 1.378 (2) |
C13A—N2A | 1.472 (2) | C5C—H5E | 0.930 |
C13A—C14A | 1.514 (2) | C6C—C8C | 1.435 (3) |
C13A—H13A | 0.970 | C6C—C7C | 1.507 (2) |
C13A—H13B | 0.970 | C7C—O2C | 1.249 (2) |
C14A—N3A | 1.489 (2) | C7C—O1C | 1.270 (2) |
C14A—H14A | 0.970 | C8C—O3C | 1.251 (2) |
C14A—H14B | 0.970 | C8C—C9C | 1.466 (2) |
C15A—N3A | 1.487 (2) | C9C—C10C | 1.407 (3) |
C15A—C16A | 1.519 (2) | C10C—C11C | 1.361 (3) |
C15A—H15A | 0.970 | C10C—H10E | 0.930 |
C15A—H15B | 0.970 | C11C—F1C | 1.360 (2) |
C16A—N2A | 1.479 (2) | C11C—C12C | 1.413 (3) |
C16A—H16A | 0.970 | C12C—C17C | 1.383 (3) |
C16A—H16B | 0.970 | C12C—N2C | 1.403 (2) |
C17A—H17A | 0.930 | C13C—N2C | 1.471 (2) |
N3A—H3A3 | 0.900 | C13C—C14C | 1.519 (3) |
N3A—H3A4 | 0.900 | C13C—H13E | 0.970 |
C1B—N1B | 1.456 (2) | C13C—H13F | 0.970 |
C1B—C2B | 1.496 (2) | C14C—N3C | 1.490 (2) |
C1B—C3B | 1.500 (3) | C14C—H14E | 0.970 |
C1B—H1C | 0.980 | C14C—H14F | 0.970 |
C2B—C3B | 1.509 (3) | C15C—N3C | 1.489 (3) |
C2B—H2C1 | 0.970 | C15C—C16C | 1.506 (3) |
C2B—H2D2 | 0.970 | C15C—H15E | 0.970 |
C3B—H3C1 | 0.970 | C15C—H15F | 0.970 |
C3B—H3D2 | 0.970 | C16C—N2C | 1.484 (2) |
C4B—N1B | 1.402 (2) | C16C—H16E | 0.970 |
C4B—C9B | 1.402 (2) | C16C—H16F | 0.970 |
C4B—C17B | 1.407 (2) | C17C—H17E | 0.930 |
C5B—N1B | 1.346 (2) | N3C—H3C4 | 0.900 |
C5B—C6B | 1.367 (3) | N3C—H3C3 | 0.900 |
C5B—H5C | 0.930 | OW8—H81 | 0.862 (10) |
C6B—C8B | 1.449 (2) | OW8—H82 | 0.864 (10) |
C6B—C7B | 1.509 (2) | OW9—H91 | 0.856 (10) |
C7B—O1B | 1.258 (2) | OW9—H92 | 0.863 (10) |
C7B—O2B | 1.262 (2) | OW10—H101 | 0.861 (10) |
C8B—O3B | 1.244 (2) | OW10—H102 | 0.869 (10) |
C8B—C9B | 1.474 (2) | OW11—H111 | 0.865 (10) |
C9B—C10B | 1.410 (2) | OW11—H112 | 0.856 (10) |
C10B—C11B | 1.363 (2) | OW12—H121 | 0.858 (10) |
C10B—H10C | 0.930 | OW12—H122 | 0.841 (10) |
C11B—F1B | 1.3641 (19) | OW13—H131 | 0.856 (10) |
C11B—C12B | 1.412 (2) | OW13—H132 | 0.850 (10) |
C12B—C17B | 1.390 (2) | OW14—H141 | 0.889 (10) |
C12B—N2B | 1.409 (2) | OW14—H142 | 0.868 (10) |
C13B—N2B | 1.470 (2) | OW15—H151 | 0.854 (10) |
C13B—C14B | 1.517 (2) | OW15—H152 | 0.821 (10) |
C13B—H13C | 0.970 | ||
N1A—C1A—C2A | 118.73 (15) | N2B—C13B—H13C | 109.6 |
N1A—C1A—C3A | 118.99 (15) | C14B—C13B—H13C | 109.6 |
C2A—C1A—C3A | 60.26 (11) | N2B—C13B—H13D | 109.6 |
N1A—C1A—H1A | 115.8 | C14B—C13B—H13D | 109.6 |
C2A—C1A—H1A | 115.8 | H13C—C13B—H13D | 108.1 |
C3A—C1A—H1A | 115.8 | N3B—C14B—C13B | 111.25 (14) |
C1A—C2A—C3A | 60.11 (11) | N3B—C14B—H14C | 109.4 |
C1A—C2A—H2A1 | 117.8 | C13B—C14B—H14C | 109.4 |
C3A—C2A—H2A1 | 117.8 | N3B—C14B—H14D | 109.4 |
C1A—C2A—H2A2 | 117.8 | C13B—C14B—H14D | 109.4 |
C3A—C2A—H2A2 | 117.8 | H14C—C14B—H14D | 108.0 |
H2A1—C2A—H2A2 | 114.9 | N3B—C15B—C16B | 110.43 (14) |
C1A—C3A—C2A | 59.63 (11) | N3B—C15B—H15C | 109.6 |
C1A—C3A—H3A1 | 117.8 | C16B—C15B—H15C | 109.6 |
C2A—C3A—H3A1 | 117.8 | N3B—C15B—H15D | 109.6 |
C1A—C3A—H3A2 | 117.8 | C16B—C15B—H15D | 109.6 |
C2A—C3A—H3A2 | 117.8 | H15C—C15B—H15D | 108.1 |
H3A1—C3A—H3A2 | 114.9 | N2B—C16B—C15B | 110.21 (14) |
N1A—C4A—C9A | 119.47 (15) | N2B—C16B—H16C | 109.6 |
N1A—C4A—C17A | 119.37 (15) | C15B—C16B—H16C | 109.6 |
C9A—C4A—C17A | 121.15 (15) | N2B—C16B—H16D | 109.6 |
N1A—C5A—C6A | 124.66 (16) | C15B—C16B—H16D | 109.6 |
N1A—C5A—H5A | 117.7 | H16C—C16B—H16D | 108.1 |
C6A—C5A—H5A | 117.7 | C12B—C17B—C4B | 120.60 (16) |
C5A—C6A—C8A | 120.10 (15) | C12B—C17B—H17C | 119.7 |
C5A—C6A—C7A | 116.51 (15) | C4B—C17B—H17C | 119.7 |
C8A—C6A—C7A | 123.38 (15) | C5B—N1B—C4B | 119.40 (14) |
O2A—C7A—O1A | 124.93 (16) | C5B—N1B—C1B | 121.16 (14) |
O2A—C7A—C6A | 118.16 (15) | C4B—N1B—C1B | 119.44 (14) |
O1A—C7A—C6A | 116.87 (16) | C12B—N2B—C13B | 114.80 (13) |
O3A—C8A—C6A | 124.85 (15) | C12B—N2B—C16B | 114.05 (13) |
O3A—C8A—C9A | 120.64 (15) | C13B—N2B—C16B | 110.00 (14) |
C6A—C8A—C9A | 114.46 (15) | C15B—N3B—C14B | 110.99 (14) |
C4A—C9A—C10A | 117.65 (15) | C15B—N3B—H3B3 | 109.4 |
C4A—C9A—C8A | 121.85 (15) | C14B—N3B—H3B3 | 109.4 |
C10A—C9A—C8A | 120.43 (15) | C15B—N3B—H3B4 | 109.4 |
C11A—C10A—C9A | 119.85 (16) | C14B—N3B—H3B4 | 109.4 |
C11A—C10A—H10A | 120.1 | H3B3—N3B—H3B4 | 108.0 |
C9A—C10A—H10A | 120.1 | N1C—C1C—C2C | 120.98 (15) |
C10A—C11A—F1A | 117.96 (15) | N1C—C1C—C3C | 119.02 (15) |
C10A—C11A—C12A | 123.61 (15) | C2C—C1C—C3C | 60.45 (12) |
F1A—C11A—C12A | 118.34 (14) | N1C—C1C—H1E | 115.2 |
C17A—C12A—N2A | 122.20 (15) | C2C—C1C—H1E | 115.2 |
C17A—C12A—C11A | 116.19 (15) | C3C—C1C—H1E | 115.2 |
N2A—C12A—C11A | 121.52 (15) | C1C—C2C—C3C | 60.15 (12) |
N2A—C13A—C14A | 111.29 (14) | C1C—C2C—H2E1 | 117.8 |
N2A—C13A—H13A | 109.4 | C3C—C2C—H2E1 | 117.8 |
C14A—C13A—H13A | 109.4 | C1C—C2C—H2F2 | 117.8 |
N2A—C13A—H13B | 109.4 | C3C—C2C—H2F2 | 117.8 |
C14A—C13A—H13B | 109.4 | H2E1—C2C—H2F2 | 114.9 |
H13A—C13A—H13B | 108.0 | C1C—C3C—C2C | 59.40 (12) |
N3A—C14A—C13A | 111.20 (14) | C1C—C3C—H3E1 | 117.8 |
N3A—C14A—H14A | 109.4 | C2C—C3C—H3E1 | 117.8 |
C13A—C14A—H14A | 109.4 | C1C—C3C—H3F2 | 117.8 |
N3A—C14A—H14B | 109.4 | C2C—C3C—H3F2 | 117.8 |
C13A—C14A—H14B | 109.4 | H3E1—C3C—H3F2 | 115.0 |
H14A—C14A—H14B | 108.0 | N1C—C4C—C9C | 118.64 (15) |
N3A—C15A—C16A | 110.34 (14) | N1C—C4C—C17C | 120.17 (16) |
N3A—C15A—H15A | 109.6 | C9C—C4C—C17C | 121.17 (16) |
C16A—C15A—H15A | 109.6 | N1C—C5C—C6C | 124.62 (16) |
N3A—C15A—H15B | 109.6 | N1C—C5C—H5E | 117.7 |
C16A—C15A—H15B | 109.6 | C6C—C5C—H5E | 117.7 |
H15A—C15A—H15B | 108.1 | C5C—C6C—C8C | 119.74 (16) |
N2A—C16A—C15A | 110.85 (14) | C5C—C6C—C7C | 117.49 (16) |
N2A—C16A—H16A | 109.5 | C8C—C6C—C7C | 122.76 (15) |
C15A—C16A—H16A | 109.5 | O2C—C7C—O1C | 124.40 (16) |
N2A—C16A—H16B | 109.5 | O2C—C7C—C6C | 119.19 (16) |
C15A—C16A—H16B | 109.5 | O1C—C7C—C6C | 116.39 (15) |
H16A—C16A—H16B | 108.1 | O3C—C8C—C6C | 124.30 (16) |
C12A—C17A—C4A | 121.23 (16) | O3C—C8C—C9C | 120.89 (16) |
C12A—C17A—H17A | 119.4 | C6C—C8C—C9C | 114.81 (15) |
C4A—C17A—H17A | 119.4 | C4C—C9C—C10C | 118.05 (16) |
C5A—N1A—C4A | 119.16 (14) | C4C—C9C—C8C | 122.34 (16) |
C5A—N1A—C1A | 120.73 (14) | C10C—C9C—C8C | 119.61 (16) |
C4A—N1A—C1A | 119.92 (14) | C11C—C10C—C9C | 119.53 (17) |
C12A—N2A—C13A | 114.72 (13) | C11C—C10C—H10E | 120.2 |
C12A—N2A—C16A | 114.86 (13) | C9C—C10C—H10E | 120.2 |
C13A—N2A—C16A | 111.41 (13) | F1C—C11C—C10C | 118.11 (17) |
C15A—N3A—C14A | 110.07 (13) | F1C—C11C—C12C | 118.16 (16) |
C15A—N3A—H3A3 | 109.6 | C10C—C11C—C12C | 123.71 (17) |
C14A—N3A—H3A3 | 109.6 | C17C—C12C—N2C | 124.13 (17) |
C15A—N3A—H3A4 | 109.6 | C17C—C12C—C11C | 116.91 (16) |
C14A—N3A—H3A4 | 109.6 | N2C—C12C—C11C | 118.95 (16) |
H3A3—N3A—H3A4 | 108.2 | N2C—C13C—C14C | 109.37 (16) |
N1B—C1B—C2B | 118.88 (15) | N2C—C13C—H13E | 109.8 |
N1B—C1B—C3B | 118.66 (15) | C14C—C13C—H13E | 109.8 |
C2B—C1B—C3B | 60.49 (12) | N2C—C13C—H13F | 109.8 |
N1B—C1B—H1C | 115.8 | C14C—C13C—H13F | 109.8 |
C2B—C1B—H1C | 115.8 | H13E—C13C—H13F | 108.2 |
C3B—C1B—H1C | 115.8 | N3C—C14C—C13C | 111.28 (15) |
C1B—C2B—C3B | 59.90 (12) | N3C—C14C—H14E | 109.4 |
C1B—C2B—H2C1 | 117.8 | C13C—C14C—H14E | 109.4 |
C3B—C2B—H2C1 | 117.8 | N3C—C14C—H14F | 109.4 |
C1B—C2B—H2D2 | 117.8 | C13C—C14C—H14F | 109.4 |
C3B—C2B—H2D2 | 117.8 | H14E—C14C—H14F | 108.0 |
H2C1—C2B—H2D2 | 114.9 | N3C—C15C—C16C | 110.83 (15) |
C1B—C3B—C2B | 59.61 (12) | N3C—C15C—H15E | 109.5 |
C1B—C3B—H3C1 | 117.8 | C16C—C15C—H15E | 109.5 |
C2B—C3B—H3C1 | 117.8 | N3C—C15C—H15F | 109.5 |
C1B—C3B—H3D2 | 117.8 | C16C—C15C—H15F | 109.5 |
C2B—C3B—H3D2 | 117.8 | H15E—C15C—H15F | 108.1 |
H3C1—C3B—H3D2 | 114.9 | N2C—C16C—C15C | 109.68 (15) |
N1B—C4B—C9B | 118.69 (15) | N2C—C16C—H16E | 109.7 |
N1B—C4B—C17B | 119.79 (15) | C15C—C16C—H16E | 109.7 |
C9B—C4B—C17B | 121.51 (15) | N2C—C16C—H16F | 109.7 |
N1B—C5B—C6B | 125.37 (16) | C15C—C16C—H16F | 109.7 |
N1B—C5B—H5C | 117.3 | H16E—C16C—H16F | 108.2 |
C6B—C5B—H5C | 117.3 | C12C—C17C—C4C | 120.53 (16) |
C5B—C6B—C8B | 119.56 (16) | C12C—C17C—H17E | 119.7 |
C5B—C6B—C7B | 116.10 (15) | C4C—C17C—H17E | 119.7 |
C8B—C6B—C7B | 124.27 (16) | C5C—N1C—C4C | 119.74 (15) |
O1B—C7B—O2B | 123.89 (16) | C5C—N1C—C1C | 121.74 (15) |
O1B—C7B—C6B | 117.96 (16) | C4C—N1C—C1C | 118.50 (14) |
O2B—C7B—C6B | 118.14 (15) | C12C—N2C—C13C | 116.74 (15) |
O3B—C8B—C6B | 125.38 (16) | C12C—N2C—C16C | 114.00 (14) |
O3B—C8B—C9B | 120.20 (15) | C13C—N2C—C16C | 109.68 (15) |
C6B—C8B—C9B | 114.40 (15) | C15C—N3C—C14C | 111.43 (15) |
C4B—C9B—C10B | 117.85 (15) | C15C—N3C—H3C4 | 109.3 |
C4B—C9B—C8B | 122.46 (15) | C14C—N3C—H3C4 | 109.3 |
C10B—C9B—C8B | 119.69 (15) | C15C—N3C—H3C3 | 109.3 |
C11B—C10B—C9B | 119.48 (16) | C14C—N3C—H3C3 | 109.3 |
C11B—C10B—H10C | 120.3 | H3C3—N3C—H3C3 | 108.0 |
C9B—C10B—H10C | 120.3 | H81—OW8—H82 | 110 (2) |
C10B—C11B—F1B | 118.33 (15) | H91—OW9—H92 | 109 (2) |
C10B—C11B—C12B | 123.95 (15) | H101—OW10—H102 | 110 (2) |
F1B—C11B—C12B | 117.68 (15) | H111—OW11—H112 | 108 (2) |
C17B—C12B—N2B | 123.35 (15) | H121—OW12—H122 | 124 (3) |
C17B—C12B—C11B | 116.47 (15) | H131—OW13—H132 | 107 (2) |
N2B—C12B—C11B | 120.13 (15) | H141—OW14—H142 | 109 (3) |
N2B—C13B—C14B | 110.37 (14) | H151—OW15—H152 | 114 (3) |
N1A—C1A—C2A—C3A | −108.87 (17) | F1B—C11B—C12B—N2B | 4.0 (2) |
N1A—C1A—C3A—C2A | 108.44 (17) | N2B—C13B—C14B—N3B | 56.51 (18) |
N1A—C5A—C6A—C8A | 2.7 (3) | N3B—C15B—C16B—N2B | −57.95 (19) |
N1A—C5A—C6A—C7A | −176.41 (16) | N2B—C12B—C17B—C4B | −179.26 (15) |
C5A—C6A—C7A—O2A | 153.83 (17) | C11B—C12B—C17B—C4B | −1.9 (2) |
C8A—C6A—C7A—O2A | −25.3 (2) | N1B—C4B—C17B—C12B | 179.50 (15) |
C5A—C6A—C7A—O1A | −24.3 (2) | C9B—C4B—C17B—C12B | −1.4 (2) |
C8A—C6A—C7A—O1A | 156.57 (17) | C6B—C5B—N1B—C4B | −3.9 (3) |
C5A—C6A—C8A—O3A | 179.70 (16) | C6B—C5B—N1B—C1B | 176.80 (16) |
C7A—C6A—C8A—O3A | −1.2 (3) | C9B—C4B—N1B—C5B | 2.0 (2) |
C5A—C6A—C8A—C9A | 2.3 (2) | C17B—C4B—N1B—C5B | −178.83 (15) |
C7A—C6A—C8A—C9A | −178.65 (15) | C9B—C4B—N1B—C1B | −178.68 (15) |
N1A—C4A—C9A—C10A | −174.15 (15) | C17B—C4B—N1B—C1B | 0.5 (2) |
C17A—C4A—C9A—C10A | 5.4 (2) | C2B—C1B—N1B—C5B | −35.8 (2) |
N1A—C4A—C9A—C8A | 3.0 (2) | C3B—C1B—N1B—C5B | −105.94 (19) |
C17A—C4A—C9A—C8A | −177.51 (15) | C2B—C1B—N1B—C4B | 144.94 (16) |
O3A—C8A—C9A—C4A | 177.45 (16) | C3B—C1B—N1B—C4B | 74.8 (2) |
C6A—C8A—C9A—C4A | −5.0 (2) | C17B—C12B—N2B—C13B | 6.7 (2) |
O3A—C8A—C9A—C10A | −5.5 (2) | C11B—C12B—N2B—C13B | −170.61 (15) |
C6A—C8A—C9A—C10A | 172.03 (15) | C17B—C12B—N2B—C16B | −121.56 (18) |
C4A—C9A—C10A—C11A | −1.6 (2) | C11B—C12B—N2B—C16B | 61.2 (2) |
C8A—C9A—C10A—C11A | −178.83 (15) | C14B—C13B—N2B—C12B | 170.59 (14) |
C9A—C10A—C11A—F1A | 172.86 (15) | C14B—C13B—N2B—C16B | −59.17 (18) |
C9A—C10A—C11A—C12A | −3.5 (3) | C15B—C16B—N2B—C12B | −169.26 (14) |
C10A—C11A—C12A—C17A | 4.8 (2) | C15B—C16B—N2B—C13B | 60.10 (18) |
F1A—C11A—C12A—C17A | −171.57 (14) | C16B—C15B—N3B—C14B | 55.05 (19) |
C10A—C11A—C12A—N2A | −178.52 (16) | C13B—C14B—N3B—C15B | −54.50 (19) |
F1A—C11A—C12A—N2A | 5.1 (2) | N1C—C1C—C2C—C3C | 108.07 (18) |
N2A—C13A—C14A—N3A | 55.52 (18) | N1C—C1C—C3C—C2C | −111.22 (18) |
N3A—C15A—C16A—N2A | −57.45 (19) | N1C—C5C—C6C—C8C | −4.1 (3) |
N2A—C12A—C17A—C4A | −177.60 (15) | N1C—C5C—C6C—C7C | 174.44 (15) |
C11A—C12A—C17A—C4A | −0.9 (2) | C5C—C6C—C7C—O2C | −158.08 (16) |
N1A—C4A—C17A—C12A | 175.42 (15) | C8C—C6C—C7C—O2C | 20.5 (3) |
C9A—C4A—C17A—C12A | −4.1 (3) | C5C—C6C—C7C—O1C | 20.4 (2) |
C6A—C5A—N1A—C4A | −5.1 (3) | C8C—C6C—C7C—O1C | −161.07 (16) |
C6A—C5A—N1A—C1A | 179.94 (16) | C5C—C6C—C8C—O3C | −176.59 (16) |
C9A—C4A—N1A—C5A | 2.1 (2) | C7C—C6C—C8C—O3C | 4.9 (3) |
C17A—C4A—N1A—C5A | −177.44 (15) | C5C—C6C—C8C—C9C | 2.7 (2) |
C9A—C4A—N1A—C1A | 177.12 (15) | C7C—C6C—C8C—C9C | −175.83 (15) |
C17A—C4A—N1A—C1A | −2.4 (2) | N1C—C4C—C9C—C10C | 179.16 (15) |
C2A—C1A—N1A—C5A | −41.2 (2) | C17C—C4C—C9C—C10C | −2.4 (2) |
C3A—C1A—N1A—C5A | −111.10 (18) | N1C—C4C—C9C—C8C | −1.5 (2) |
C2A—C1A—N1A—C4A | 143.87 (16) | C17C—C4C—C9C—C8C | 176.92 (16) |
C3A—C1A—N1A—C4A | 73.9 (2) | O3C—C8C—C9C—C4C | 179.29 (16) |
C17A—C12A—N2A—C13A | 0.2 (2) | C6C—C8C—C9C—C4C | 0.0 (2) |
C11A—C12A—N2A—C13A | −176.26 (15) | O3C—C8C—C9C—C10C | −1.4 (3) |
C17A—C12A—N2A—C16A | −130.78 (17) | C6C—C8C—C9C—C10C | 179.31 (16) |
C11A—C12A—N2A—C16A | 52.7 (2) | C4C—C9C—C10C—C11C | 1.2 (3) |
C14A—C13A—N2A—C12A | 172.25 (14) | C8C—C9C—C10C—C11C | −178.12 (16) |
C14A—C13A—N2A—C16A | −55.09 (18) | C9C—C10C—C11C—F1C | −176.68 (16) |
C15A—C16A—N2A—C12A | −171.26 (14) | C9C—C10C—C11C—C12C | 1.8 (3) |
C15A—C16A—N2A—C13A | 56.16 (18) | F1C—C11C—C12C—C17C | 174.93 (15) |
C16A—C15A—N3A—C14A | 57.54 (18) | C10C—C11C—C12C—C17C | −3.5 (3) |
C13A—C14A—N3A—C15A | −56.72 (18) | F1C—C11C—C12C—N2C | −3.7 (2) |
N1B—C1B—C2B—C3B | −108.50 (18) | C10C—C11C—C12C—N2C | 177.80 (17) |
N1B—C1B—C3B—C2B | 108.85 (18) | N2C—C13C—C14C—N3C | −57.0 (2) |
N1B—C5B—C6B—C8B | 2.4 (3) | N3C—C15C—C16C—N2C | 57.8 (2) |
N1B—C5B—C6B—C7B | −174.69 (16) | N2C—C12C—C17C—C4C | −179.16 (16) |
C5B—C6B—C7B—O1B | −12.3 (2) | C11C—C12C—C17C—C4C | 2.3 (3) |
C8B—C6B—C7B—O1B | 170.77 (16) | N1C—C4C—C17C—C12C | 179.02 (16) |
C5B—C6B—C7B—O2B | 166.61 (16) | C9C—C4C—C17C—C12C | 0.6 (3) |
C8B—C6B—C7B—O2B | −10.3 (3) | C6C—C5C—N1C—C4C | 2.5 (3) |
C5B—C6B—C8B—O3B | 179.39 (17) | C6C—C5C—N1C—C1C | −176.19 (16) |
C7B—C6B—C8B—O3B | −3.8 (3) | C9C—C4C—N1C—C5C | 0.3 (2) |
C5B—C6B—C8B—C9B | 0.9 (2) | C17C—C4C—N1C—C5C | −178.11 (15) |
C7B—C6B—C8B—C9B | 177.68 (15) | C9C—C4C—N1C—C1C | 179.11 (15) |
N1B—C4B—C9B—C10B | −178.26 (15) | C17C—C4C—N1C—C1C | 0.7 (2) |
C17B—C4B—C9B—C10B | 2.6 (2) | C2C—C1C—N1C—C5C | 26.9 (2) |
N1B—C4B—C9B—C8B | 1.1 (2) | C3C—C1C—N1C—C5C | 98.0 (2) |
C17B—C4B—C9B—C8B | −177.97 (15) | C2C—C1C—N1C—C4C | −151.79 (16) |
O3B—C8B—C9B—C4B | 178.87 (16) | C3C—C1C—N1C—C4C | −80.7 (2) |
C6B—C8B—C9B—C4B | −2.5 (2) | C17C—C12C—N2C—C13C | −11.0 (3) |
O3B—C8B—C9B—C10B | −1.7 (2) | C11C—C12C—N2C—C13C | 167.59 (16) |
C6B—C8B—C9B—C10B | 176.85 (15) | C17C—C12C—N2C—C16C | 118.60 (19) |
C4B—C9B—C10B—C11B | −0.5 (2) | C11C—C12C—N2C—C16C | −62.8 (2) |
C8B—C9B—C10B—C11B | −179.91 (15) | C14C—C13C—N2C—C12C | −167.24 (16) |
C9B—C10B—C11B—F1B | 174.64 (15) | C14C—C13C—N2C—C16C | 61.17 (19) |
C9B—C10B—C11B—C12B | −3.0 (3) | C15C—C16C—N2C—C12C | 164.97 (16) |
C10B—C11B—C12B—C17B | 4.2 (3) | C15C—C16C—N2C—C13C | −62.01 (19) |
F1B—C11B—C12B—C17B | −173.48 (14) | C16C—C15C—N3C—C14C | −53.8 (2) |
C10B—C11B—C12B—N2B | −178.37 (16) | C13C—C14C—N3C—C15C | 53.4 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3A—H3A3···O2Ci | 0.90 | 2.03 | 2.866 (2) | 153 |
N3A—H3A3···O3Ci | 0.90 | 2.29 | 2.903 (2) | 125 |
N3A—H3A4···O2Aii | 0.90 | 1.80 | 2.684 (2) | 166 |
N3B—H3B3···O3Aii | 0.90 | 1.90 | 2.782 (3) | 168 |
N3B—H3B4···O2Bii | 0.90 | 1.76 | 2.660 (2) | 173 |
N3C—H3C4···O1Ciii | 0.90 | 1.79 | 2.682 (2) | 170 |
N3C—H3C3···OW5Aiii | 0.90 | 2.29 | 2.959 (4) | 131 |
N3C—H3C3···O3Biv | 0.90 | 2.10 | 2.859 (2) | 142 |
OW8—H81···O1Aiv | 0.86 (1) | 1.86 (1) | 2.702 (2) | 165 (3) |
OW8—H82···O3C | 0.86 (3) | 1.83 (3) | 2.683 (3) | 170 (3) |
OW9—H91···O2Aiv | 0.86 (2) | 2.07 (2) | 2.836 (2) | 149 (2) |
OW9—H91···O3Aiv | 0.86 (2) | 2.38 (2) | 3.021 (2) | 133 (2) |
OW9—H92···O1Av | 0.86 (2) | 1.92 (2) | 2.784 (2) | 176 (2) |
OW10—H101···O1Bii | 0.86 (3) | 1.96 (3) | 2.816 (2) | 179 (3) |
OW10—H102···O2Bi | 0.87 (2) | 1.99 (2) | 2.826 (2) | 158 (3) |
OW10—H102···O3Bi | 0.87 (2) | 2.52 (3) | 3.091 (2) | 126 (2) |
OW11—H111···O2Cvi | 0.87 (3) | 1.97 (3) | 2.830 (2) | 175 (2) |
OW11—H112···O1C | 0.86 (1) | 1.88 (1) | 2.731 (2) | 176 (2) |
OW15—H152···O1Bii | 0.82 (3) | 1.99 (3) | 2.787 (3) | 163 (4) |
OW12—H121···OW9i | 0.86 (3) | 1.86 (3) | 2.712 (2) | 176 (3) |
OW12—H122···OW3A | 0.84 (3) | 2.20 (3) | 2.825 (4) | 131 (3) |
OW12—H122···OW5B | 0.84 (3) | 2.06 (3) | 2.882 (5) | 165 (3) |
OW13—H131···OW8vi | 0.86 (2) | 1.96 (2) | 2.803 (3) | 166 (2) |
OW13—H132···OW1Avii | 0.85 (3) | 2.16 (3) | 2.930 (4) | 150 (3) |
OW13—H132···OW6A | 0.85 (3) | 2.41 (3) | 2.827 (5) | 111 (2) |
OW14—H141···OW1A | 0.89 (1) | 2.25 (2) | 2.910 (4) | 131 (2) |
OW14—H141···OW1B | 0.89 (1) | 2.03 (3) | 2.623 (5) | 123 (3) |
OW14—H142···OW8i | 0.86 (4) | 1.91 (4) | 2.728 (3) | 157 (3) |
OW15—H151···OW4Ai | 0.85 (3) | 1.91 (3) | 2.75 (3) | 170 (4) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z; (iii) x−1, y, z; (iv) −x, −y+1, −z+1; (v) x+1, y+1, z; (vi) −x+1, −y+1, −z; (vii) x, y, z−1. |
Experimental details
(I) | (II) | |
Crystal data | ||
Chemical formula | 2C17H18FN3O3·3C2H4F2O | 3C17H18FN3O3·14.5H2O |
Mr | 908.84 | 1255.26 |
Crystal system, space group | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 120 | 100 |
a, b, c (Å) | 10.9848 (4), 13.9800 (4), 13.9802 (4) | 13.8760 (12), 15.8760 (13), 16.528 (2) |
α, β, γ (°) | 105.6488 (18), 90.352 (2), 93.364 (2) | 115.755 (7), 103.610 (7), 102.325 (5) |
V (Å3) | 2063.22 (11) | 2972.8 (5) |
Z | 2 | 2 |
Radiation type | Synchrotron, λ = 0.7000 Å | Mo Kα |
µ (mm−1) | 0.13 | 0.12 |
Crystal size (mm) | 0.1 × 0.08 × 0.08 | 0.30 × 0.25 × 0.20 |
Data collection | ||
Diffractometer | Bruker SMART APEXII CCD area-detector diffractometer | Bruker APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (TWINABS; Sheldrick, 2008a) | Multi-scan (SADABS; Sheldrick, 2008a) |
Tmin, Tmax | 0.58, 0.74 | 0.40, 0.43 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 51821, 7072, 5962 | 55842, 12150, 9655 |
Rint | 0.08 | 0.038 |
(sin θ/λ)max (Å−1) | 0.596 | 0.625 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.068, 0.202, 1.16 | 0.043, 0.122, 1.03 |
No. of reflections | 7072 | 12150 |
No. of parameters | 571 | 907 |
No. of restraints | 522 | 34 |
H-atom treatment | H-atom parameters constrained | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.58, −0.46 | 0.57, −0.42 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008b), SHELXL97 (Sheldrick, 2008b), ORTEP-3 for Windows (Burnett & Johnson, 1996) and Mercury (Macrae et al., 2008), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
N3A—H3A3···O1Ai | 0.90 | 2.58 | 3.176 (4) | 125 |
N3A—H3A3···O2Ai | 0.90 | 1.86 | 2.758 (4) | 173 |
N3A—H3A4···O2Bii | 0.90 | 2.39 | 2.885 (4) | 114 |
N3A—H3A4···O3Bii | 0.90 | 1.85 | 2.717 (4) | 162 |
N3B—H3B3···O1Biii | 0.90 | 2.77 | 3.376 (4) | 126 |
N3B—H3B3···O2Biii | 0.90 | 1.82 | 2.724 (4) | 179 |
N3B—H3B4···O2Aiv | 0.90 | 2.50 | 2.894 (4) | 107 |
N3B—H3B4···O3Aiv | 0.90 | 1.79 | 2.687 (4) | 171 |
O4A—H4A···O1Av | 0.82 | 1.88 | 2.672 (4) | 162 |
O4B—H4B···O1Bii | 0.82 | 1.87 | 2.666 (4) | 165 |
O4C—H4C···O1Bv | 0.82 | 1.93 | 2.733 (4) | 168 |
C2A—H2A2···F3Bii | 0.97 | 2.51 | 3.207 (5) | 128 |
C14A—H14A···O2Avi | 0.97 | 2.49 | 3.350 (5) | 148 |
C14A—H14A···O3Avi | 0.97 | 2.49 | 3.274 (4) | 138 |
C16A—H16A···O4Bvii | 0.97 | 2.48 | 3.148 (5) | 126 |
C1B—H1B···F2C | 0.98 | 2.45 | 3.200 (5) | 133 |
C14B—H14D···O2Bii | 0.97 | 2.34 | 3.295 (4) | 170 |
C15B—H15D···O2Aiv | 0.97 | 2.51 | 3.131 (5) | 122 |
C18B—H18D···F1B | 0.97 | 2.46 | 3.396 (5) | 161 |
Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+1, −z+1; (iii) x, y+1, z; (iv) −x+1, −y+2, −z+2; (v) −x+1, −y+1, −z+2; (vi) −x+2, −y+2, −z+2; (vii) −x+1, −y+2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3A—H3A3···O2Ci | 0.90 | 2.03 | 2.866 (2) | 153 |
N3A—H3A3···O3Ci | 0.90 | 2.29 | 2.903 (2) | 125 |
N3A—H3A4···O2Aii | 0.90 | 1.80 | 2.684 (2) | 166 |
N3B—H3B3···O3Aii | 0.90 | 1.90 | 2.782 (3) | 168 |
N3B—H3B4···O2Bii | 0.90 | 1.76 | 2.660 (2) | 173 |
N3C—H3C4···O1Ciii | 0.90 | 1.79 | 2.682 (2) | 170 |
N3C—H3C3···OW5Aiii | 0.90 | 2.29 | 2.959 (4) | 131 |
N3C—H3C3···O3Biv | 0.90 | 2.10 | 2.859 (2) | 142 |
OW8—H81···O1Aiv | 0.862 (14) | 1.861 (14) | 2.702 (2) | 165 (3) |
OW8—H82···O3C | 0.86 (3) | 1.83 (3) | 2.683 (3) | 170 (3) |
OW9—H91···O2Aiv | 0.855 (19) | 2.067 (19) | 2.836 (2) | 149 (2) |
OW9—H91···O3Aiv | 0.855 (19) | 2.38 (2) | 3.021 (2) | 132.9 (18) |
OW9—H92···O1Av | 0.86 (2) | 1.92 (2) | 2.784 (2) | 176.1 (19) |
OW10—H101···O1Bii | 0.86 (3) | 1.96 (3) | 2.816 (2) | 179 (3) |
OW10—H102···O2Bi | 0.87 (2) | 1.99 (2) | 2.826 (2) | 158 (3) |
OW10—H102···O3Bi | 0.87 (2) | 2.52 (3) | 3.091 (2) | 126 (2) |
OW11—H111···O2Cvi | 0.87 (3) | 1.97 (3) | 2.830 (2) | 175 (2) |
OW11—H112···O1C | 0.858 (14) | 1.876 (13) | 2.731 (2) | 176 (2) |
OW15—H152···O1Bii | 0.82 (3) | 1.99 (3) | 2.787 (3) | 163 (4) |
OW12—H121···OW9i | 0.86 (3) | 1.86 (3) | 2.712 (2) | 176 (3) |
OW12—H122···OW3A | 0.84 (3) | 2.20 (3) | 2.825 (4) | 131 (3) |
OW12—H122···OW5B | 0.84 (3) | 2.06 (3) | 2.882 (5) | 165 (3) |
OW13—H131···OW8vi | 0.86 (2) | 1.96 (2) | 2.803 (3) | 166 (2) |
OW13—H132···OW1Avii | 0.85 (3) | 2.16 (3) | 2.930 (4) | 150 (3) |
OW13—H132···OW6A | 0.85 (3) | 2.41 (3) | 2.827 (5) | 111 (2) |
OW14—H141···OW1A | 0.888 (13) | 2.25 (2) | 2.910 (4) | 131 (2) |
OW14—H141···OW1B | 0.888 (13) | 2.03 (3) | 2.623 (5) | 123 (3) |
OW14—H142···OW8i | 0.86 (4) | 1.91 (4) | 2.728 (3) | 157 (3) |
OW15—H151···OW4Ai | 0.85 (3) | 1.91 (3) | 2.75 (3) | 170 (4) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z; (iii) x−1, y, z; (iv) −x, −y+1, −z+1; (v) x+1, y+1, z; (vi) −x+1, −y+1, −z; (vii) x, y, z−1. |
θ1 = C2—C1—N1—C5, θ2 = C5—C6—C7—O1 and θ3 = C11—C12—N2—C16. |
Molecule | θ1 | θ2 | θ3 |
(I) A | 37.9 (5) | -3.0 (5) | -58.0 (4) |
(I) B | -30.5 (6) | 0.3 (5) | 60.4 (4) |
(II) A | -41.2 (2) | -24.3 (2) | 52.7 (2) |
(II) B | -35.8 (2) | -12.3 (2) | 61.2 (2) |
(II) C | 26.9 (2) | 20.4 (2) | -62.8 (2) |
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Ciprofloxacin (Cf) belongs to the quinolone class of semisynthetic antibiotics (Turel, 2002; Mitscher, 2005). A search of the Cambridge Structural Database (Version 5.31 with updates to May 2010; Allen, 2002) reveals 68 crystal structures containing the Cf molecule. These include the structures of the anhydrous form (Fabbiani et al., 2009; Mahapatra et al., 2010), a hexahydrate (Turel et al., 1997; Fabbiani & Dittrich, 2008), hydrated sodium salts crystallized under high-pressure conditions and recoverable to ambient pressure (Fabbiani et al., 2009), a lactate sesquihydrate (Prasanna & Guru Row, 2001), a hemi-methanolate (Li et al., 2006), a hydrochloride 1.34-hydrate (Turel & Golobič, 2003), and several coordination complexes with group II or lanthanide elements.
While the crystal structures of coordination complexes of Cf often contain more than one Cf molecule in the asymmetric unit, (I) and (II) are the only examples known to date of non-coordination complexes where this is the case: two and three independent Cf molecules are found in (I) and (II), respectively (Figs. 1 and 2). Some differences in torsion angles are observed for the Cf molecules in the two structures (Table 1), indicating conformational variations in the relative orientation of the piperazinium ring and, in particular, of the cyclopropyl and carboxylate groups relative to the planar dihydroquinoline ring structure. In both (I) and (II), Cf exists as a zwitterion. Previous literature (Główka et al. 2003) has suggested that an in-plane conformation for quinolones, as observed for (I), is predominantly associated with a protonated carboxyl group, with exceptions being characterized by significant differences in C—O bond lengths compared with those normally observed in zwitterions. For (I) and (II), we are confident of our zwitterionic assignment on the basis of (i) the observed bond lengths of the carboxylate group, which, although significantly different for most of the molecules, are well below the expected value of 1.31 Å for a C—OH single bond [Reference for standard value?], and (ii) the fact that the H atoms of the NH2+ groups are visible in difference Fourier maps.
The supramolecular architecture of both structures is dominated by three-dimensional hydrogen-bonding patterns, with different hydrogen-bonding capabilities satisfied by the symmetry-independent Cf molecules. Hydrogen-bond parameters are given in Tables 2 and 3. In (I), both Cf molecules form similarly bifurcated N—H···O(carboxylate) hydrogen bonds that define cross-linked chains of molecules A and B running in nearly perpendicular directions along the c and b axes, respectively. Symmetry-equivalent chains stack pairwise via face-to-face π–π interactions. Each of the three symmetry-independent 2,2-difluoroethanol molecules donates a hydrogen bond to the carboxylate O atom antiperiplanar to the carbonyl group: 2,2-difluoroethanol molecules B and C to Cf molecule B, and 2,2-difluoroethanol molecule A to Cf molecule A. These hydrogen bonds, together with weaker C—H···F and C—H···O interactions, contribute to the formation of the three-dimensional network (Fig. 3). The conformation of the hydroxyl group differs in the three independent 2,2-difluoroethanol molecules, with values for the C19—C18—O4—H4 torsion angle of 151, 98 and 160° for molecules A, B and C, respectively.
Although significant disorder is observed for the water molecules in (II), hydrogen bonds involving the Cf molecules are well defined, since the majority of water molecules interacting directly with Cf are ordered and their H-atom positions could be assigned from the experimental data. As in (I), each of the symmetry-independent Cf molecules forms infinite hydrogen-bonded N—H···O(carboxylate) chains. In (II), however, the hydrogen bonds in these chains are not bifurcated and involve N—H34 rather than N—H33. In addition, rather than being nearly orthogonal to each other, the chains all run along the a axis. Cross-linking of the chains occurs via a second set of N—H···O(carbonyl) hydrogen bonds, leading to the formation of trimers about a pseudo-31screw axis. This is in marked contrast with the structure of Cf hexahydrate, which forms a layered structure with no direct Cf···Cf contacts (Turel et al., 1997; Fabbiani & Dittrich, 2008 ?). The trimers in (II) are arranged in a hexameric fashion centred about the inversion centre at the unit-cell origin (Fig. 4). This arrangement creates channels approximately 4.5 Å in diameter that contain predominantly disordered water molecules (OW1–OW7 and OW15), as well as those that were modelled as ordered but exhibit the largest displacement parameters (OW12–OW14). The better defined water molecules, OW8–OW11, act as hydrogen-bond donor bridges, linking molecules within a trimer (OW8) and pairs of symmetry-related molecules (OW9–OW11), thereby connecting the trimers (Fig. 4 and Table 3). Within the hexameric arrangement, face-to-face π–π interactions link symmetry-equivalent Cf hydrogen-bonded chains in a manner similar to that found for the pairwise stacks of hydrogen-bonded chains in (I), albeit at slightly larger interplanar separations [3.4854 (8), 3.4980 (9) and 3.6165 (7) Å for pairwise stacks of molecules A, B and C, respectively, in (II); 3.2642 (14) and 3.4023 (14) Å for molecules A and B, respectively, in (I)]. As in the structure of (I), there are a number of C—H···O, C—H···F and C—H···π interactions that contribute to the stability of the structure.
Hirshfeld surfaces (Spackman & Byrom, 1997; McKinnon et al., 1998) and fingerprint plots (Spackman & McKinnon, 2002) have been shown to be useful tools for comparing and elucidating intermolecular interactions of molecules in different crystalline environments, including symmetry-independent molecules in the asymmetric unit (McKinnon et al., 2004, 2007). The analysis of fingerprint plots is restricted here to the structure of (I), since several water H atoms are missing from the structure of (II). Fingerprint plots for the two symmetry-independent Cf molecules and three symmetry-independent 2,2-difluoroethanol molecules in (I) are shown in Figs. 5 and 6, respectively. At first glance, the plots for Cf look quite similar in shape, which reflects the not-too-dissimilar packing environment around the two molecules. On closer inspection, the `thickness' and point density of some features, e.g. the long spikes denoting hydrogen bonding or the regions at high values of de and di, are distinct for each molecule. The asymmetry about the plot diagonal is typical of a structure that contains more than one molecule in the crystallographic asymmetric unit. Some interactions, e.g. H···H, O···H, H···O and C···H, labelled in Fig. 5 as 1, 2, 3 and 4, respectively, manifest themselves with characteristic features in the plots. For instance, it is immediately obvious that two distinct C···H interactions, namely π···H, are present, and on comparison with the plots shown in Fig. 6, the complementary H···π interactions are visible: Cf molecule A with solvent molecule C, and Cf molecule B with solvent molecule A, while solvent molecule B does not participate in such contacts. The diffuse set of points labelled 5 in Fig. 6 corresponds to H···H contacts involved in a cyclic interaction; the hydroxyl atoms O4 and H4 of solvent molecule A are approximately coplanar with atoms O1 and H5 of Cf molecule A, so that, in addition to the stronger O4—H4···O1 hydrogen bond, a much weaker C5—H5···O4 interaction [C5···O4 = 3.669 (5) Å] is also present.