Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314617014249/sj4138sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2414314617014249/sj4138Isup2.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314617014249/sj4138Isup3.cml |
CCDC reference: 1577756
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.005 Å
- Disorder in main residue
- R factor = 0.052
- wR factor = 0.145
- Data-to-parameter ratio = 17.5
checkCIF/PLATON results
No syntax errors found
Alert level C STRVA01_ALERT_4_C Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.490 From the CIF: _refine_ls_abs_structure_Flack_su 0.160 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.60 Report PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00467 Ang. PLAT420_ALERT_2_C D-H Without Acceptor N4 -- H4B ... Please Check PLAT480_ALERT_4_C Long H...A H-Bond Reported H4B .. CL1 .. 2.92 Ang.
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 9 Note PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ... 12 Report PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 3 Report PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check PLAT093_ALERT_1_G No s.u.'s on H-positions, Refinement Reported as mixed Check PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records 8 Report PLAT174_ALERT_4_G The CIF-Embedded .res File Contains FLAT Records 2 Report PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records 3 Report PLAT186_ALERT_4_G The CIF-Embedded .res File Contains ISOR Records 1 Report PLAT301_ALERT_3_G Main Residue Disorder ..............(Resd 1).. 32% Note PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms .... ! Info PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 84 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 8 Note PLAT961_ALERT_5_G Dataset Contains no Negative Intensities ....... Please Check PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 7 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 5 ALERT level C = Check. Ensure it is not caused by an omission or oversight 15 ALERT level G = General information/check it is not something unexpected 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 7 ALERT type 4 Improvement, methodology, query or suggestion 3 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing
Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
C18H17ClN4O2 | Dx = 1.423 Mg m−3 |
Mr = 356.80 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pna21 | Cell parameters from 6865 reflections |
a = 24.258 (3) Å | θ = 2.2–27.5° |
b = 4.6484 (5) Å | µ = 0.25 mm−1 |
c = 14.7708 (16) Å | T = 100 K |
V = 1665.6 (3) Å3 | Block, colorless |
Z = 4 | 0.25 × 0.16 × 0.05 mm |
F(000) = 744 |
Bruker SMART APEX CCD diffractometer | 4036 independent reflections |
Radiation source: fine-focus sealed tube | 3379 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
Detector resolution: 8.3333 pixels mm-1 | θmax = 28.3°, θmin = 1.7° |
ω scans | h = −32→32 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −6→6 |
Tmin = 0.94, Tmax = 0.99 | l = −19→19 |
7372 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.052 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.145 | w = 1/[σ2(Fo2) + (0.0818P)2 + 0.3986P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
4036 reflections | Δρmax = 0.77 e Å−3 |
231 parameters | Δρmin = −0.30 e Å−3 |
84 restraints | Absolute structure: Refined as an inversion twin |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.49 (16) |
Experimental. The diffraction data were collected in three sets of 363 frames (0.5° width in ω) at φ = 0, 120 and 240°. A scan time of 180 sec/frame was used. |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
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 > 2sigma(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. The 2-chlorobenzyl group is disordered over several closely spaced positions. After several attempts, the only feasible model was a 2-site one treating the rings as rigid hexagons. H-atoms attached to carbon were placed in idealized positions while those attached to nitrogen were placed in locations derived from a difference map and their coordinates adjusted to give N—H = 0.91 %A. All were included as riding contributions. Refined as a 2-component inversion twin. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.57433 (10) | 0.7964 (6) | 0.42015 (17) | 0.0305 (6) | |
O2 | 0.43551 (10) | 0.6782 (5) | 0.38490 (17) | 0.0267 (5) | |
N1 | 0.50239 (11) | 0.8913 (6) | 0.51467 (18) | 0.0231 (6) | |
N2 | 0.54455 (12) | 0.4766 (6) | 0.63241 (19) | 0.0242 (6) | |
N3 | 0.41985 (12) | 1.1092 (6) | 0.3195 (2) | 0.0263 (6) | |
H3A | 0.4245 | 1.3014 | 0.3283 | 0.034 (11)* | |
N4 | 0.38670 (13) | 0.9972 (7) | 0.2490 (2) | 0.0317 (7) | |
H4A | 0.4043 | 0.8569 | 0.2173 | 0.044 (13)* | |
H4B | 0.3559 | 0.9345 | 0.2781 | 0.038 (12)* | |
C1 | 0.49487 (13) | 0.6127 (7) | 0.6508 (2) | 0.0233 (6) | |
C2 | 0.46541 (15) | 0.5374 (8) | 0.7293 (2) | 0.0293 (7) | |
H2 | 0.4799 | 0.3950 | 0.7688 | 0.035* | |
C3 | 0.41607 (16) | 0.6664 (9) | 0.7498 (2) | 0.0339 (8) | |
H3 | 0.3969 | 0.6161 | 0.8036 | 0.041* | |
C4 | 0.39449 (15) | 0.8702 (9) | 0.6914 (3) | 0.0374 (9) | |
H4 | 0.3602 | 0.9581 | 0.7056 | 0.045* | |
C5 | 0.42163 (15) | 0.9485 (8) | 0.6132 (3) | 0.0312 (8) | |
H5 | 0.4059 | 1.0881 | 0.5740 | 0.037* | |
C6 | 0.47239 (14) | 0.8223 (7) | 0.5917 (2) | 0.0234 (7) | |
C7 | 0.55016 (14) | 0.7508 (7) | 0.4917 (2) | 0.0234 (6) | |
C8 | 0.57052 (13) | 0.5406 (7) | 0.5594 (2) | 0.0237 (7) | |
C9 | 0.48067 (14) | 1.0949 (7) | 0.4481 (2) | 0.0246 (7) | |
H9A | 0.5116 | 1.1848 | 0.4147 | 0.030* | |
H9B | 0.4600 | 1.2491 | 0.4795 | 0.030* | |
C10 | 0.44243 (13) | 0.9402 (7) | 0.3812 (2) | 0.0215 (6) | |
C11 | 0.62385 (13) | 0.3913 (7) | 0.5368 (2) | 0.0261 (7) | |
H11A | 0.6205 | 0.3004 | 0.4764 | 0.031* | |
H11B | 0.6305 | 0.2368 | 0.5816 | 0.031* | |
Cl1 | 0.74190 (7) | 0.3151 (6) | 0.69305 (14) | 0.0692 (6) | 0.675 (3) |
C12 | 0.6744 (3) | 0.6004 (17) | 0.5363 (5) | 0.0297 (18) | 0.675 (3) |
H12A | 0.6689 | 0.7525 | 0.4903 | 0.036* | 0.675 (3) |
H12B | 0.6783 | 0.6934 | 0.5963 | 0.036* | 0.675 (3) |
C13 | 0.72605 (16) | 0.4260 (10) | 0.5144 (3) | 0.0332 (14) | 0.675 (3) |
C14 | 0.75662 (17) | 0.2843 (10) | 0.5803 (3) | 0.0384 (14) | 0.675 (3) |
C15 | 0.80138 (15) | 0.1150 (10) | 0.5555 (4) | 0.0494 (16) | 0.675 (3) |
H15 | 0.8223 | 0.0182 | 0.6005 | 0.059* | 0.675 (3) |
C16 | 0.81556 (16) | 0.0875 (11) | 0.4647 (4) | 0.054 (2) | 0.675 (3) |
H16 | 0.8462 | −0.0281 | 0.4477 | 0.065* | 0.675 (3) |
C17 | 0.7850 (2) | 0.2293 (13) | 0.3988 (3) | 0.061 (2) | 0.675 (3) |
H17 | 0.7947 | 0.2105 | 0.3367 | 0.073* | 0.675 (3) |
C18 | 0.7402 (2) | 0.3985 (12) | 0.4236 (3) | 0.0528 (18) | 0.675 (3) |
H18 | 0.7193 | 0.4953 | 0.3786 | 0.063* | 0.675 (3) |
Cl1A | 0.71901 (15) | 0.5143 (12) | 0.3615 (3) | 0.0692 (6) | 0.325 (3) |
C12A | 0.6753 (6) | 0.566 (4) | 0.5630 (14) | 0.0297 (18) | 0.325 (3) |
H12C | 0.6766 | 0.7474 | 0.5279 | 0.036* | 0.325 (3) |
H12D | 0.6742 | 0.6146 | 0.6282 | 0.036* | 0.325 (3) |
C13A | 0.7262 (4) | 0.383 (2) | 0.5423 (8) | 0.0332 (14) | 0.325 (3) |
C14A | 0.7474 (4) | 0.345 (2) | 0.4556 (7) | 0.0384 (14) | 0.325 (3) |
C15A | 0.7933 (4) | 0.171 (2) | 0.4423 (6) | 0.0494 (16) | 0.325 (3) |
H15A | 0.8077 | 0.1451 | 0.3830 | 0.059* | 0.325 (3) |
C16A | 0.8180 (4) | 0.035 (2) | 0.5155 (8) | 0.054 (2) | 0.325 (3) |
H16A | 0.8494 | −0.0840 | 0.5064 | 0.065* | 0.325 (3) |
C17A | 0.7969 (4) | 0.073 (3) | 0.6022 (7) | 0.061 (2) | 0.325 (3) |
H17A | 0.8138 | −0.0203 | 0.6523 | 0.073* | 0.325 (3) |
C18A | 0.7510 (5) | 0.247 (3) | 0.6156 (6) | 0.0528 (18) | 0.325 (3) |
H18A | 0.7365 | 0.2725 | 0.6748 | 0.063* | 0.325 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0359 (13) | 0.0295 (13) | 0.0259 (12) | −0.0008 (10) | 0.0010 (10) | 0.0006 (10) |
O2 | 0.0348 (12) | 0.0148 (10) | 0.0304 (12) | −0.0028 (9) | −0.0054 (10) | 0.0007 (9) |
N1 | 0.0264 (13) | 0.0183 (12) | 0.0245 (13) | −0.0020 (11) | −0.0054 (11) | −0.0004 (11) |
N2 | 0.0259 (13) | 0.0234 (14) | 0.0232 (13) | 0.0003 (11) | −0.0059 (11) | −0.0006 (11) |
N3 | 0.0324 (14) | 0.0174 (13) | 0.0292 (15) | −0.0031 (11) | −0.0085 (11) | 0.0012 (11) |
N4 | 0.0362 (16) | 0.0261 (15) | 0.0328 (16) | −0.0027 (13) | −0.0106 (13) | −0.0001 (12) |
C1 | 0.0261 (15) | 0.0233 (15) | 0.0204 (14) | −0.0009 (12) | −0.0041 (12) | −0.0023 (12) |
C2 | 0.0308 (18) | 0.0328 (18) | 0.0244 (16) | −0.0013 (14) | −0.0047 (13) | 0.0016 (15) |
C3 | 0.0319 (18) | 0.045 (2) | 0.0244 (17) | −0.0014 (16) | 0.0015 (14) | −0.0027 (16) |
C4 | 0.0275 (17) | 0.043 (2) | 0.042 (2) | 0.0081 (16) | 0.0027 (15) | −0.0094 (18) |
C5 | 0.0309 (18) | 0.0278 (19) | 0.0349 (19) | 0.0032 (14) | −0.0048 (14) | 0.0001 (14) |
C6 | 0.0278 (16) | 0.0187 (15) | 0.0237 (15) | −0.0005 (12) | −0.0061 (12) | −0.0018 (12) |
C7 | 0.0272 (16) | 0.0187 (15) | 0.0243 (15) | −0.0028 (12) | −0.0031 (11) | −0.0032 (12) |
C8 | 0.0227 (15) | 0.0202 (15) | 0.0281 (16) | −0.0022 (12) | −0.0061 (12) | −0.0025 (13) |
C9 | 0.0303 (16) | 0.0157 (15) | 0.0278 (16) | 0.0013 (13) | −0.0063 (12) | 0.0034 (12) |
C10 | 0.0248 (14) | 0.0176 (15) | 0.0221 (14) | −0.0005 (11) | 0.0016 (12) | −0.0009 (12) |
C11 | 0.0271 (15) | 0.0237 (16) | 0.0276 (16) | 0.0028 (13) | −0.0033 (13) | −0.0019 (13) |
Cl1 | 0.0429 (8) | 0.1067 (17) | 0.0581 (9) | −0.0183 (9) | −0.0076 (7) | 0.0194 (11) |
C12 | 0.0289 (18) | 0.025 (3) | 0.036 (5) | 0.0000 (18) | −0.001 (3) | 0.000 (3) |
C13 | 0.0282 (18) | 0.026 (2) | 0.045 (4) | −0.0052 (17) | 0.005 (2) | −0.004 (3) |
C14 | 0.023 (2) | 0.035 (3) | 0.057 (4) | −0.004 (2) | 0.001 (2) | 0.003 (3) |
C15 | 0.023 (2) | 0.040 (3) | 0.085 (4) | −0.003 (2) | 0.000 (3) | 0.002 (3) |
C16 | 0.033 (2) | 0.043 (3) | 0.086 (6) | −0.004 (2) | 0.017 (4) | −0.023 (4) |
C17 | 0.051 (3) | 0.062 (4) | 0.068 (4) | −0.015 (3) | 0.019 (3) | −0.014 (3) |
C18 | 0.043 (3) | 0.053 (4) | 0.062 (4) | −0.011 (3) | 0.005 (3) | −0.001 (3) |
Cl1A | 0.0429 (8) | 0.1067 (17) | 0.0581 (9) | −0.0183 (9) | −0.0076 (7) | 0.0194 (11) |
C12A | 0.0289 (18) | 0.025 (3) | 0.036 (5) | 0.0000 (18) | −0.001 (3) | 0.000 (3) |
C13A | 0.0282 (18) | 0.026 (2) | 0.045 (4) | −0.0052 (17) | 0.005 (2) | −0.004 (3) |
C14A | 0.023 (2) | 0.035 (3) | 0.057 (4) | −0.004 (2) | 0.001 (2) | 0.003 (3) |
C15A | 0.023 (2) | 0.040 (3) | 0.085 (4) | −0.003 (2) | 0.000 (3) | 0.002 (3) |
C16A | 0.033 (2) | 0.043 (3) | 0.086 (6) | −0.004 (2) | 0.017 (4) | −0.023 (4) |
C17A | 0.051 (3) | 0.062 (4) | 0.068 (4) | −0.015 (3) | 0.019 (3) | −0.014 (3) |
C18A | 0.043 (3) | 0.053 (4) | 0.062 (4) | −0.011 (3) | 0.005 (3) | −0.001 (3) |
O1—C7 | 1.227 (4) | C11—H11B | 0.9900 |
O2—C10 | 1.231 (4) | Cl1—C14 | 1.709 (4) |
N1—C7 | 1.373 (4) | C12—C13 | 1.528 (8) |
N1—C6 | 1.389 (4) | C12—H12A | 0.9900 |
N1—C9 | 1.463 (4) | C12—H12B | 0.9900 |
N2—C8 | 1.284 (5) | C13—C14 | 1.3900 |
N2—C1 | 1.388 (4) | C13—C18 | 1.3900 |
N3—C10 | 1.323 (4) | C14—C15 | 1.3900 |
N3—N4 | 1.414 (4) | C15—C16 | 1.3900 |
N3—H3A | 0.9099 | C15—H15 | 0.9500 |
N4—H4A | 0.9100 | C16—C17 | 1.3900 |
N4—H4B | 0.9100 | C16—H16 | 0.9500 |
C1—C2 | 1.407 (5) | C17—C18 | 1.3900 |
C1—C6 | 1.416 (4) | C17—H17 | 0.9500 |
C2—C3 | 1.372 (5) | C18—H18 | 0.9500 |
C2—H2 | 0.9500 | Cl1A—C14A | 1.740 (9) |
C3—C4 | 1.384 (6) | C12A—C13A | 1.533 (18) |
C3—H3 | 0.9500 | C12A—H12C | 0.9900 |
C4—C5 | 1.378 (6) | C12A—H12D | 0.9900 |
C4—H4 | 0.9500 | C13A—C14A | 1.3900 |
C5—C6 | 1.401 (5) | C13A—C18A | 1.3900 |
C5—H5 | 0.9500 | C14A—C15A | 1.3900 |
C7—C8 | 1.483 (5) | C15A—C16A | 1.3900 |
C8—C11 | 1.506 (4) | C15A—H15A | 0.9500 |
C9—C10 | 1.533 (4) | C16A—C17A | 1.3900 |
C9—H9A | 0.9900 | C16A—H16A | 0.9500 |
C9—H9B | 0.9900 | C17A—C18A | 1.3900 |
C11—C12A | 1.538 (16) | C17A—H17A | 0.9500 |
C11—C12 | 1.564 (8) | C18A—H18A | 0.9500 |
C11—H11A | 0.9900 | ||
C7—N1—C6 | 122.4 (3) | H11A—C11—H11B | 107.8 |
C7—N1—C9 | 116.4 (3) | C13—C12—C11 | 108.3 (5) |
C6—N1—C9 | 120.8 (3) | C13—C12—H12A | 110.0 |
C8—N2—C1 | 119.0 (3) | C11—C12—H12A | 110.0 |
C10—N3—N4 | 121.6 (3) | C13—C12—H12B | 110.0 |
C10—N3—H3A | 115.7 | C11—C12—H12B | 110.0 |
N4—N3—H3A | 122.5 | H12A—C12—H12B | 108.4 |
N3—N4—H4A | 112.1 | C14—C13—C18 | 120.0 |
N3—N4—H4B | 103.7 | C14—C13—C12 | 122.7 (4) |
H4A—N4—H4B | 113.5 | C18—C13—C12 | 117.2 (4) |
N2—C1—C2 | 119.2 (3) | C15—C14—C13 | 120.0 |
N2—C1—C6 | 121.8 (3) | C15—C14—Cl1 | 117.9 (3) |
C2—C1—C6 | 118.9 (3) | C13—C14—Cl1 | 122.1 (3) |
C3—C2—C1 | 121.0 (3) | C14—C15—C16 | 120.0 |
C3—C2—H2 | 119.5 | C14—C15—H15 | 120.0 |
C1—C2—H2 | 119.5 | C16—C15—H15 | 120.0 |
C2—C3—C4 | 119.5 (3) | C17—C16—C15 | 120.0 |
C2—C3—H3 | 120.3 | C17—C16—H16 | 120.0 |
C4—C3—H3 | 120.3 | C15—C16—H16 | 120.0 |
C5—C4—C3 | 121.5 (3) | C16—C17—C18 | 120.0 |
C5—C4—H4 | 119.3 | C16—C17—H17 | 120.0 |
C3—C4—H4 | 119.3 | C18—C17—H17 | 120.0 |
C4—C5—C6 | 120.0 (3) | C17—C18—C13 | 120.0 |
C4—C5—H5 | 120.0 | C17—C18—H18 | 120.0 |
C6—C5—H5 | 120.0 | C13—C18—H18 | 120.0 |
N1—C6—C5 | 123.4 (3) | C13A—C12A—C11 | 108.1 (11) |
N1—C6—C1 | 117.5 (3) | C13A—C12A—H12C | 110.1 |
C5—C6—C1 | 119.1 (3) | C11—C12A—H12C | 110.1 |
O1—C7—N1 | 122.3 (3) | C13A—C12A—H12D | 110.1 |
O1—C7—C8 | 122.4 (3) | C11—C12A—H12D | 110.1 |
N1—C7—C8 | 115.3 (3) | H12C—C12A—H12D | 108.4 |
N2—C8—C7 | 123.8 (3) | C14A—C13A—C18A | 120.0 |
N2—C8—C11 | 120.1 (3) | C14A—C13A—C12A | 123.5 (10) |
C7—C8—C11 | 116.1 (3) | C18A—C13A—C12A | 116.5 (10) |
N1—C9—C10 | 110.3 (3) | C15A—C14A—C13A | 120.0 |
N1—C9—H9A | 109.6 | C15A—C14A—Cl1A | 117.8 (6) |
C10—C9—H9A | 109.6 | C13A—C14A—Cl1A | 122.2 (6) |
N1—C9—H9B | 109.6 | C14A—C15A—C16A | 120.0 |
C10—C9—H9B | 109.6 | C14A—C15A—H15A | 120.0 |
H9A—C9—H9B | 108.1 | C16A—C15A—H15A | 120.0 |
O2—C10—N3 | 124.2 (3) | C15A—C16A—C17A | 120.0 |
O2—C10—C9 | 121.2 (3) | C15A—C16A—H16A | 120.0 |
N3—C10—C9 | 114.6 (3) | C17A—C16A—H16A | 120.0 |
C8—C11—C12A | 113.4 (8) | C18A—C17A—C16A | 120.0 |
C8—C11—C12 | 112.8 (4) | C18A—C17A—H17A | 120.0 |
C8—C11—H11A | 109.0 | C16A—C17A—H17A | 120.0 |
C12—C11—H11A | 109.0 | C17A—C18A—C13A | 120.0 |
C8—C11—H11B | 109.0 | C17A—C18A—H18A | 120.0 |
C12—C11—H11B | 109.0 | C13A—C18A—H18A | 120.0 |
C8—N2—C1—C2 | 178.2 (3) | N2—C8—C11—C12A | −97.9 (9) |
C8—N2—C1—C6 | −0.7 (5) | C7—C8—C11—C12A | 84.3 (9) |
N2—C1—C2—C3 | −179.8 (3) | N2—C8—C11—C12 | −115.1 (4) |
C6—C1—C2—C3 | −0.9 (5) | C7—C8—C11—C12 | 67.1 (4) |
C1—C2—C3—C4 | 1.1 (6) | C8—C11—C12—C13 | 179.0 (4) |
C2—C3—C4—C5 | −0.4 (6) | C11—C12—C13—C14 | −86.4 (5) |
C3—C4—C5—C6 | −0.4 (6) | C11—C12—C13—C18 | 89.8 (4) |
C7—N1—C6—C5 | −175.4 (3) | C18—C13—C14—C15 | 0.0 |
C9—N1—C6—C5 | −3.0 (5) | C12—C13—C14—C15 | 176.2 (5) |
C7—N1—C6—C1 | 4.5 (4) | C18—C13—C14—Cl1 | 178.8 (4) |
C9—N1—C6—C1 | 176.9 (3) | C12—C13—C14—Cl1 | −5.0 (5) |
C4—C5—C6—N1 | −179.5 (3) | C13—C14—C15—C16 | 0.0 |
C4—C5—C6—C1 | 0.6 (5) | Cl1—C14—C15—C16 | −178.9 (4) |
N2—C1—C6—N1 | −1.0 (5) | C14—C15—C16—C17 | 0.0 |
C2—C1—C6—N1 | −179.8 (3) | C15—C16—C17—C18 | 0.0 |
N2—C1—C6—C5 | 178.9 (3) | C16—C17—C18—C13 | 0.0 |
C2—C1—C6—C5 | 0.1 (5) | C14—C13—C18—C17 | 0.0 |
C6—N1—C7—O1 | 174.3 (3) | C12—C13—C18—C17 | −176.4 (4) |
C9—N1—C7—O1 | 1.6 (5) | C8—C11—C12A—C13A | 176.3 (8) |
C6—N1—C7—C8 | −5.9 (4) | C11—C12A—C13A—C14A | 77.5 (13) |
C9—N1—C7—C8 | −178.6 (3) | C11—C12A—C13A—C18A | −101.4 (12) |
C1—N2—C8—C7 | −1.0 (5) | C18A—C13A—C14A—C15A | 0.0 |
C1—N2—C8—C11 | −178.6 (3) | C12A—C13A—C14A—C15A | −178.9 (9) |
O1—C7—C8—N2 | −176.0 (3) | C18A—C13A—C14A—Cl1A | −178.8 (9) |
N1—C7—C8—N2 | 4.2 (5) | C12A—C13A—C14A—Cl1A | 2.3 (11) |
O1—C7—C8—C11 | 1.8 (4) | C13A—C14A—C15A—C16A | 0.0 |
N1—C7—C8—C11 | −178.1 (3) | Cl1A—C14A—C15A—C16A | 178.9 (8) |
C7—N1—C9—C10 | 88.2 (3) | C14A—C15A—C16A—C17A | 0.0 |
C6—N1—C9—C10 | −84.6 (3) | C15A—C16A—C17A—C18A | 0.0 |
N4—N3—C10—O2 | −2.4 (5) | C16A—C17A—C18A—C13A | 0.0 |
N4—N3—C10—C9 | 175.5 (3) | C14A—C13A—C18A—C17A | 0.0 |
N1—C9—C10—O2 | −3.5 (4) | C12A—C13A—C18A—C17A | 179.0 (8) |
N1—C9—C10—N3 | 178.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O2i | 0.91 | 1.96 | 2.842 (4) | 163 |
N4—H4A···N2ii | 0.91 | 2.35 | 3.256 (4) | 175 |
N4—H4B···Cl1ii | 0.91 | 2.92 | 3.539 (3) | 126 |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+1, z−1/2. |