


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989023010812/hb8089sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2056989023010812/hb8089I_250Ksup2.hkl |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2056989023010812/hb8089I_100Ksup3.hkl |
CCDC references: 2314991; 2314990
Key indicators
Structure: I_250K- Single-crystal X-ray study
- T = 250 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.041
- wR factor = 0.102
- Data-to-parameter ratio = 29.2
- Single-crystal X-ray study
- T = 100 K
- Mean
(C-C) = 0.001 Å
- R factor = 0.033
- wR factor = 0.075
- Data-to-parameter ratio = 53.6
checkCIF/PLATON results
No syntax errors found Datablock: I_250K
Alert level C PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 5.947 Check
Alert level G PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 6 Report H1N H2N H3N H4N H5N H6N PLAT300_ALERT_4_G Atom Site Occupancy of H1N Constrained at 0.5 Check PLAT300_ALERT_4_G Atom Site Occupancy of H2N Constrained at 0.5 Check PLAT300_ALERT_4_G Atom Site Occupancy of H3N Constrained at 0.5 Check PLAT300_ALERT_4_G Atom Site Occupancy of H4N Constrained at 0.5 Check PLAT300_ALERT_4_G Atom Site Occupancy of H5N Constrained at 0.5 Check PLAT300_ALERT_4_G Atom Site Occupancy of H6N Constrained at 0.5 Check PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary . Please Do ! PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 6 Note PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File 1 Note 2 0 0, PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 7 Info PLAT992_ALERT_5_G Repd & Actual _reflns_number_gt Values Differ by 2 Check
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 1 ALERT level C = Check. Ensure it is not caused by an omission or oversight 12 ALERT level G = General information/check it is not something unexpected 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 7 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
Datablock: I_100K
Alert level C PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 18 Report -2 1 1, -2 2 1, -1 2 1, -1 3 1, -1 4 1, -2 0 2, -1 0 2, 0 0 2, -2 1 2, -2 2 2, -1 2 2, -2 3 2, -1 3 2, -1 4 2, -2 5 2, -1 1 3, -1 2 3, -1 3 3,
Alert level G PLAT480_ALERT_4_G Long H...A H-Bond Reported H2 ..CL1 . 2.98 Ang. PLAT870_ALERT_4_G ALERTS Related to Twinning Effects Suppressed .. ! Info PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 266 Note PLAT931_ALERT_5_G CIFcalcFCF Twin Law ( 1 0 0) Est.d BASF 0.44 Check PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File 1 Note 0 0 2, PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ........... 4.4 Low PLAT992_ALERT_5_G Repd & Actual _reflns_number_gt Values Differ by 2 Check
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 1 ALERT level C = Check. Ensure it is not caused by an omission or oversight 7 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
C7H10NO+·Cl− | Dx = 1.304 Mg m−3 |
Mr = 159.61 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 9997 reflections |
a = 8.8689 (4) Å | θ = 3.8–27.4° |
b = 8.4361 (3) Å | µ = 0.40 mm−1 |
c = 21.7319 (9) Å | T = 250 K |
V = 1625.96 (12) Å3 | Lath fragment, pink |
Z = 8 | 0.34 × 0.31 × 0.15 mm |
F(000) = 672 |
Bruker Kappa APEXII CCD diffractometer | 2717 independent reflections |
Radiation source: fine-focus sealed tube | 2019 reflections with I > 2σ(I) |
TRIUMPH curved graphite monochromator | Rint = 0.050 |
φ and ω scans | θmax = 31.6°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −13→13 |
Tmin = 0.896, Tmax = 0.942 | k = −12→12 |
73425 measured reflections | l = −32→32 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.041 | w = 1/[σ2(Fo2) + (0.0348P)2 + 0.6343P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.102 | (Δ/σ)max = 0.001 |
S = 1.08 | Δρmax = 0.24 e Å−3 |
2717 reflections | Δρmin = −0.21 e Å−3 |
93 parameters | Extinction correction: SHELXL-2017/1 (Sheldrick 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0070 (9) |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cl1 | 0.74847 (4) | 0.51434 (4) | 0.52125 (2) | 0.03992 (12) | |
O1 | 0.65326 (14) | 0.80202 (15) | 0.20491 (5) | 0.0514 (3) | |
N1 | 0.52441 (19) | 0.75043 (18) | 0.45535 (6) | 0.0547 (4) | |
H1N | 0.584233 | 0.818422 | 0.475901 | 0.082* | 0.5 |
H2N | 0.427238 | 0.776832 | 0.461481 | 0.082* | 0.5 |
H3N | 0.540574 | 0.651270 | 0.469129 | 0.082* | 0.5 |
H4N | 0.450464 | 0.679260 | 0.461773 | 0.082* | 0.5 |
H5N | 0.607459 | 0.720851 | 0.476193 | 0.082* | 0.5 |
H6N | 0.494123 | 0.846412 | 0.468545 | 0.082* | 0.5 |
C1 | 0.55894 (17) | 0.75820 (17) | 0.38936 (7) | 0.0388 (3) | |
C2 | 0.48090 (17) | 0.66401 (19) | 0.34891 (7) | 0.0427 (3) | |
H2 | 0.408003 | 0.592462 | 0.363560 | 0.051* | |
C3 | 0.51002 (17) | 0.67476 (19) | 0.28628 (7) | 0.0406 (3) | |
H3 | 0.456473 | 0.610978 | 0.258349 | 0.049* | |
C4 | 0.61767 (17) | 0.77925 (17) | 0.26521 (6) | 0.0371 (3) | |
C5 | 0.6976 (2) | 0.8710 (2) | 0.30673 (8) | 0.0481 (4) | |
H5 | 0.772702 | 0.940379 | 0.292416 | 0.058* | |
C6 | 0.6681 (2) | 0.8615 (2) | 0.36875 (7) | 0.0484 (4) | |
H6 | 0.721776 | 0.924909 | 0.396768 | 0.058* | |
C7 | 0.5863 (2) | 0.6992 (3) | 0.16061 (8) | 0.0638 (5) | |
H7A | 0.611485 | 0.590164 | 0.170382 | 0.096* | |
H7B | 0.624205 | 0.725123 | 0.119973 | 0.096* | |
H7C | 0.477664 | 0.712315 | 0.161343 | 0.096* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.03990 (18) | 0.04090 (19) | 0.03894 (18) | −0.00135 (14) | −0.00086 (16) | 0.00395 (13) |
O1 | 0.0576 (7) | 0.0614 (7) | 0.0351 (6) | 0.0028 (6) | 0.0091 (5) | 0.0037 (5) |
N1 | 0.0653 (9) | 0.0622 (9) | 0.0364 (7) | 0.0194 (7) | 0.0085 (6) | 0.0064 (6) |
C1 | 0.0407 (7) | 0.0429 (7) | 0.0328 (6) | 0.0138 (6) | 0.0038 (6) | 0.0053 (6) |
C2 | 0.0373 (7) | 0.0436 (8) | 0.0473 (8) | −0.0006 (6) | 0.0065 (6) | 0.0055 (6) |
C3 | 0.0375 (8) | 0.0435 (8) | 0.0407 (7) | 0.0009 (6) | 0.0001 (6) | −0.0035 (6) |
C4 | 0.0375 (7) | 0.0391 (7) | 0.0347 (7) | 0.0073 (6) | 0.0040 (6) | 0.0036 (5) |
C5 | 0.0484 (9) | 0.0496 (9) | 0.0463 (9) | −0.0129 (7) | 0.0036 (7) | 0.0052 (7) |
C6 | 0.0528 (9) | 0.0504 (9) | 0.0419 (8) | −0.0056 (7) | −0.0049 (7) | −0.0028 (7) |
C7 | 0.0643 (12) | 0.0896 (14) | 0.0374 (8) | 0.0102 (11) | 0.0031 (8) | −0.0106 (9) |
O1—C4 | 1.3615 (17) | C2—C3 | 1.388 (2) |
O1—C7 | 1.425 (2) | C2—H2 | 0.9400 |
N1—C1 | 1.4679 (19) | C3—C4 | 1.378 (2) |
N1—H1N | 0.9000 | C3—H3 | 0.9400 |
N1—H2N | 0.9000 | C4—C5 | 1.384 (2) |
N1—H3N | 0.9000 | C5—C6 | 1.375 (2) |
N1—H4N | 0.9000 | C5—H5 | 0.9400 |
N1—H5N | 0.9000 | C6—H6 | 0.9400 |
N1—H6N | 0.9000 | C7—H7A | 0.9700 |
C1—C2 | 1.372 (2) | C7—H7B | 0.9700 |
C1—C6 | 1.377 (2) | C7—H7C | 0.9700 |
C4—O1—C7 | 117.88 (14) | C4—C3—C2 | 119.77 (14) |
C1—N1—H1N | 109.5 | C4—C3—H3 | 120.1 |
C1—N1—H2N | 109.5 | C2—C3—H3 | 120.1 |
H1N—N1—H2N | 109.5 | O1—C4—C3 | 124.81 (14) |
C1—N1—H3N | 109.5 | O1—C4—C5 | 115.46 (14) |
H1N—N1—H3N | 109.5 | C3—C4—C5 | 119.73 (13) |
H2N—N1—H3N | 109.5 | C6—C5—C4 | 120.60 (15) |
C1—N1—H4N | 109.5 | C6—C5—H5 | 119.7 |
C1—N1—H5N | 109.5 | C4—C5—H5 | 119.7 |
H4N—N1—H5N | 109.5 | C5—C6—C1 | 119.28 (15) |
C1—N1—H6N | 109.5 | C5—C6—H6 | 120.4 |
H4N—N1—H6N | 109.5 | C1—C6—H6 | 120.4 |
H5N—N1—H6N | 109.5 | O1—C7—H7A | 109.5 |
C2—C1—C6 | 120.83 (14) | O1—C7—H7B | 109.5 |
C2—C1—N1 | 119.65 (14) | H7A—C7—H7B | 109.5 |
C6—C1—N1 | 119.51 (15) | O1—C7—H7C | 109.5 |
C1—C2—C3 | 119.76 (14) | H7A—C7—H7C | 109.5 |
C1—C2—H2 | 120.1 | H7B—C7—H7C | 109.5 |
C3—C2—H2 | 120.1 | ||
C6—C1—C2—C3 | −1.2 (2) | C2—C3—C4—C5 | 1.0 (2) |
N1—C1—C2—C3 | 177.97 (14) | O1—C4—C5—C6 | 178.05 (15) |
C1—C2—C3—C4 | 0.4 (2) | C3—C4—C5—C6 | −1.5 (2) |
C7—O1—C4—C3 | −7.0 (2) | C4—C5—C6—C1 | 0.7 (3) |
C7—O1—C4—C5 | 173.48 (15) | C2—C1—C6—C5 | 0.7 (2) |
C2—C3—C4—O1 | −178.58 (14) | N1—C1—C6—C5 | −178.52 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···Cl1i | 0.90 | 2.43 | 3.3265 (18) | 174 |
N1—H2N···Cl1ii | 0.90 | 2.40 | 3.1915 (15) | 147 |
N1—H3N···CL1 | 0.90 | 2.45 | 3.1570 (16) | 135 |
N1—H4N···Cl1iii | 0.90 | 2.43 | 3.3323 (18) | 180 |
N1—H5N···Cl1 | 0.90 | 2.36 | 3.1570 (15) | 148 |
N1—H6N···Cl1ii | 0.90 | 2.49 | 3.1915 (17) | 136 |
C6—H6···Cl1i | 0.94 | 2.82 | 3.6323 (16) | 145 |
Symmetry codes: (i) −x+3/2, y+1/2, z; (ii) x−1/2, −y+3/2, −z+1; (iii) −x+1, −y+1, −z+1. |
C7H10NO+·Cl− | F(000) = 672 |
Mr = 159.61 | Dx = 1.330 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.3039 (6) Å | Cell parameters from 9875 reflections |
b = 21.6993 (15) Å | θ = 3.4–41.5° |
c = 8.8495 (6) Å | µ = 0.41 mm−1 |
β = 90.077 (2)° | T = 100 K |
V = 1594.58 (19) Å3 | Needle fragment, pink |
Z = 8 | 0.43 × 0.41 × 0.21 mm |
Bruker Kappa APEXII CCD diffractometer | 10832 independent reflections |
Radiation source: fine-focus sealed tube | 9310 reflections with I > 2σ(I) |
TRIUMPH curved graphite monochromator | Rint = 0.033 |
φ and ω scans | θmax = 41.9°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −15→15 |
Tmin = 0.873, Tmax = 0.919 | k = −40→40 |
48397 measured reflections | l = −16→15 |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.033 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.075 | w = 1/[σ2(Fo2) + (0.0336P)2 + 0.1702P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
10832 reflections | Δρmax = 0.47 e Å−3 |
202 parameters | Δρmin = −0.28 e Å−3 |
0 restraints |
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. Refined as a 2-component twin |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.46961 (2) | 0.52412 (2) | 0.74414 (2) | 0.01433 (3) | |
Cl2 | 1.00704 (2) | 0.51981 (2) | 0.75416 (2) | 0.01431 (3) | |
O1 | 0.81503 (9) | 0.79863 (3) | 0.36295 (8) | 0.01972 (12) | |
N1 | 0.75005 (10) | 0.54837 (3) | 0.50236 (8) | 0.01524 (11) | |
H11N | 0.8313 (18) | 0.5382 (6) | 0.5613 (16) | 0.023* | |
H12N | 0.7496 (18) | 0.5254 (6) | 0.4219 (16) | 0.023* | |
H13N | 0.6580 (18) | 0.5390 (6) | 0.5566 (17) | 0.023* | |
C1 | 0.75955 (9) | 0.61391 (3) | 0.46333 (8) | 0.01282 (11) | |
C2 | 0.66656 (10) | 0.65590 (4) | 0.54219 (9) | 0.01463 (13) | |
H2 | 0.592916 | 0.642048 | 0.616899 | 0.018* | |
C3 | 0.68159 (10) | 0.71877 (4) | 0.51130 (9) | 0.01510 (12) | |
H3 | 0.618985 | 0.747903 | 0.565734 | 0.018* | |
C4 | 0.78835 (10) | 0.73857 (3) | 0.40075 (9) | 0.01439 (12) | |
C5 | 0.87901 (11) | 0.69542 (4) | 0.31922 (10) | 0.01746 (14) | |
H5 | 0.949889 | 0.708935 | 0.241833 | 0.021* | |
C6 | 0.86556 (10) | 0.63310 (4) | 0.35115 (10) | 0.01644 (13) | |
H6 | 0.928009 | 0.603820 | 0.297051 | 0.020* | |
C7 | 0.71299 (15) | 0.84409 (4) | 0.43121 (12) | 0.02472 (19) | |
H7A | 0.600193 | 0.834617 | 0.408214 | 0.037* | |
H7B | 0.739987 | 0.884893 | 0.391123 | 0.037* | |
H7C | 0.729058 | 0.843809 | 0.540940 | 0.037* | |
O2 | 0.69262 (8) | 0.20673 (3) | 0.82982 (8) | 0.01905 (11) | |
N2 | 0.73702 (9) | 0.45944 (3) | 0.94929 (8) | 0.01440 (11) | |
H21N | 0.7316 (18) | 0.4677 (6) | 1.0489 (16) | 0.022* | |
H22N | 0.6576 (18) | 0.4795 (6) | 0.9008 (16) | 0.022* | |
H23N | 0.8253 (18) | 0.4776 (6) | 0.9085 (16) | 0.022* | |
C8 | 0.72962 (9) | 0.39304 (3) | 0.91915 (8) | 0.01249 (11) | |
C9 | 0.82458 (10) | 0.35313 (4) | 1.00292 (9) | 0.01498 (12) | |
H9 | 0.895113 | 0.368738 | 1.078368 | 0.018* | |
C10 | 0.81599 (10) | 0.28992 (3) | 0.97583 (9) | 0.01480 (12) | |
H10 | 0.880248 | 0.262235 | 1.033186 | 0.018* | |
C11 | 0.71267 (9) | 0.26745 (3) | 0.86417 (9) | 0.01383 (12) | |
C12 | 0.61959 (10) | 0.30835 (4) | 0.77920 (10) | 0.01777 (14) | |
H12 | 0.550715 | 0.293062 | 0.702026 | 0.021* | |
C13 | 0.62716 (10) | 0.37124 (4) | 0.80690 (10) | 0.01671 (13) | |
H13 | 0.563053 | 0.399067 | 0.749807 | 0.020* | |
C14 | 0.80131 (12) | 0.16348 (4) | 0.89757 (11) | 0.02172 (16) | |
H14A | 0.912339 | 0.174734 | 0.872250 | 0.033* | |
H14B | 0.778211 | 0.122036 | 0.859247 | 0.033* | |
H14C | 0.787721 | 0.164090 | 1.007547 | 0.033* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.01254 (6) | 0.01532 (6) | 0.01511 (7) | −0.00041 (5) | −0.00015 (8) | 0.00016 (6) |
Cl2 | 0.01256 (6) | 0.01453 (6) | 0.01584 (7) | −0.00127 (5) | −0.00072 (8) | −0.00022 (6) |
O1 | 0.0248 (3) | 0.0133 (2) | 0.0211 (3) | −0.0012 (2) | −0.0017 (2) | 0.0031 (2) |
N1 | 0.0200 (3) | 0.0126 (2) | 0.0132 (3) | −0.0018 (2) | −0.0019 (2) | 0.00002 (19) |
C1 | 0.0144 (3) | 0.0126 (2) | 0.0114 (3) | −0.0006 (2) | −0.0012 (2) | −0.0003 (2) |
C2 | 0.0154 (3) | 0.0155 (3) | 0.0130 (3) | −0.0001 (2) | 0.0007 (2) | −0.0002 (2) |
C3 | 0.0168 (3) | 0.0149 (3) | 0.0136 (3) | 0.0019 (2) | −0.0001 (2) | −0.0010 (2) |
C4 | 0.0158 (3) | 0.0133 (3) | 0.0140 (3) | −0.0011 (2) | −0.0034 (2) | 0.0009 (2) |
C5 | 0.0187 (3) | 0.0169 (3) | 0.0168 (3) | −0.0015 (3) | 0.0047 (3) | 0.0013 (3) |
C6 | 0.0182 (3) | 0.0150 (3) | 0.0161 (3) | 0.0007 (2) | 0.0037 (3) | −0.0010 (2) |
C7 | 0.0372 (6) | 0.0143 (3) | 0.0226 (4) | 0.0052 (3) | −0.0034 (4) | 0.0003 (3) |
O2 | 0.0220 (3) | 0.0129 (2) | 0.0222 (3) | −0.0016 (2) | −0.0008 (2) | −0.0029 (2) |
N2 | 0.0182 (3) | 0.0126 (2) | 0.0124 (3) | −0.0008 (2) | 0.0008 (2) | 0.00002 (19) |
C8 | 0.0136 (3) | 0.0124 (2) | 0.0115 (3) | −0.0012 (2) | 0.0008 (2) | −0.0003 (2) |
C9 | 0.0166 (3) | 0.0149 (3) | 0.0134 (3) | −0.0003 (2) | −0.0026 (3) | −0.0014 (2) |
C10 | 0.0169 (3) | 0.0139 (3) | 0.0136 (3) | 0.0007 (2) | −0.0013 (2) | −0.0006 (2) |
C11 | 0.0147 (3) | 0.0129 (3) | 0.0139 (3) | −0.0023 (2) | 0.0023 (2) | −0.0014 (2) |
C12 | 0.0193 (3) | 0.0160 (3) | 0.0180 (4) | −0.0021 (2) | −0.0055 (3) | −0.0018 (2) |
C13 | 0.0181 (3) | 0.0153 (3) | 0.0167 (3) | −0.0010 (2) | −0.0050 (3) | 0.0011 (2) |
C14 | 0.0280 (4) | 0.0136 (3) | 0.0236 (4) | 0.0022 (3) | 0.0032 (3) | −0.0011 (3) |
O1—C4 | 1.3636 (10) | O2—C11 | 1.3624 (9) |
O1—C7 | 1.4343 (12) | O2—C14 | 1.4330 (11) |
N1—C1 | 1.4655 (10) | N2—C8 | 1.4667 (10) |
N1—H11N | 0.880 (15) | N2—H21N | 0.901 (14) |
N1—H12N | 0.870 (14) | N2—H22N | 0.899 (14) |
N1—H13N | 0.926 (15) | N2—H23N | 0.907 (15) |
C1—C2 | 1.3838 (11) | C8—C9 | 1.3856 (11) |
C1—C6 | 1.3915 (11) | C8—C13 | 1.3900 (11) |
C2—C3 | 1.3971 (11) | C9—C10 | 1.3941 (11) |
C2—H2 | 0.9500 | C9—H9 | 0.9500 |
C3—C4 | 1.3893 (12) | C10—C11 | 1.3957 (11) |
C3—H3 | 0.9500 | C10—H10 | 0.9500 |
C4—C5 | 1.4020 (12) | C11—C12 | 1.3961 (11) |
C5—C6 | 1.3860 (11) | C12—C13 | 1.3879 (11) |
C5—H5 | 0.9500 | C12—H12 | 0.9500 |
C6—H6 | 0.9500 | C13—H13 | 0.9500 |
C7—H7A | 0.9800 | C14—H14A | 0.9800 |
C7—H7B | 0.9800 | C14—H14B | 0.9800 |
C7—H7C | 0.9800 | C14—H14C | 0.9800 |
C4—O1—C7 | 117.24 (7) | C11—O2—C14 | 117.60 (7) |
C1—N1—H11N | 109.9 (9) | C8—N2—H21N | 111.7 (8) |
C1—N1—H12N | 111.4 (9) | C8—N2—H22N | 111.0 (8) |
H11N—N1—H12N | 110.1 (13) | H21N—N2—H22N | 109.5 (12) |
C1—N1—H13N | 112.4 (8) | C8—N2—H23N | 112.8 (8) |
H11N—N1—H13N | 105.7 (12) | H21N—N2—H23N | 110.2 (13) |
H12N—N1—H13N | 107.2 (13) | H22N—N2—H23N | 101.1 (12) |
C2—C1—C6 | 121.11 (7) | C9—C8—C13 | 121.13 (7) |
C2—C1—N1 | 119.33 (7) | C9—C8—N2 | 119.54 (7) |
C6—C1—N1 | 119.53 (7) | C13—C8—N2 | 119.32 (7) |
C1—C2—C3 | 119.63 (8) | C8—C9—C10 | 119.60 (7) |
C1—C2—H2 | 120.2 | C8—C9—H9 | 120.2 |
C3—C2—H2 | 120.2 | C10—C9—H9 | 120.2 |
C4—C3—C2 | 119.81 (7) | C9—C10—C11 | 119.78 (7) |
C4—C3—H3 | 120.1 | C9—C10—H10 | 120.1 |
C2—C3—H3 | 120.1 | C11—C10—H10 | 120.1 |
O1—C4—C3 | 124.91 (7) | O2—C11—C10 | 124.79 (7) |
O1—C4—C5 | 115.12 (7) | O2—C11—C12 | 115.29 (7) |
C3—C4—C5 | 119.96 (7) | C10—C11—C12 | 119.91 (7) |
C6—C5—C4 | 120.22 (8) | C13—C12—C11 | 120.33 (7) |
C6—C5—H5 | 119.9 | C13—C12—H12 | 119.8 |
C4—C5—H5 | 119.9 | C11—C12—H12 | 119.8 |
C5—C6—C1 | 119.26 (7) | C12—C13—C8 | 119.23 (7) |
C5—C6—H6 | 120.4 | C12—C13—H13 | 120.4 |
C1—C6—H6 | 120.4 | C8—C13—H13 | 120.4 |
O1—C7—H7A | 109.5 | O2—C14—H14A | 109.5 |
O1—C7—H7B | 109.5 | O2—C14—H14B | 109.5 |
H7A—C7—H7B | 109.5 | H14A—C14—H14B | 109.5 |
O1—C7—H7C | 109.5 | O2—C14—H14C | 109.5 |
H7A—C7—H7C | 109.5 | H14A—C14—H14C | 109.5 |
H7B—C7—H7C | 109.5 | H14B—C14—H14C | 109.5 |
C6—C1—C2—C3 | −1.43 (12) | C13—C8—C9—C10 | −0.84 (12) |
N1—C1—C2—C3 | 176.47 (7) | N2—C8—C9—C10 | 179.11 (7) |
C1—C2—C3—C4 | 0.67 (12) | C8—C9—C10—C11 | 0.36 (12) |
C7—O1—C4—C3 | −6.94 (12) | C14—O2—C11—C10 | −9.35 (12) |
C7—O1—C4—C5 | 173.41 (8) | C14—O2—C11—C12 | 171.16 (8) |
C2—C3—C4—O1 | −178.79 (8) | C9—C10—C11—O2 | −178.87 (8) |
C2—C3—C4—C5 | 0.84 (12) | C9—C10—C11—C12 | 0.60 (12) |
O1—C4—C5—C6 | 178.02 (8) | O2—C11—C12—C13 | 178.42 (8) |
C3—C4—C5—C6 | −1.65 (12) | C10—C11—C12—C13 | −1.10 (13) |
C4—C5—C6—C1 | 0.91 (13) | C11—C12—C13—C8 | 0.63 (13) |
C2—C1—C6—C5 | 0.63 (12) | C9—C8—C13—C12 | 0.35 (13) |
N1—C1—C6—C5 | −177.26 (8) | N2—C8—C13—C12 | −179.60 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11N···Cl2 | 0.880 (15) | 2.279 (15) | 3.1450 (8) | 167.7 (13) |
N1—H12N···Cl1i | 0.870 (14) | 2.573 (14) | 3.2480 (7) | 135.2 (13) |
N1—H12N···Cl2ii | 0.870 (14) | 2.735 (15) | 3.3797 (8) | 132.1 (12) |
N1—H13N···Cl1 | 0.926 (15) | 2.304 (16) | 3.2080 (8) | 165.0 (13) |
N2—H21N···Cl1iii | 0.901 (14) | 2.487 (15) | 3.2318 (8) | 140.3 (12) |
N2—H21N···Cl2iv | 0.901 (14) | 2.795 (14) | 3.4047 (8) | 126.2 (11) |
N2—H22N···Cl1 | 0.899 (14) | 2.300 (15) | 3.1916 (8) | 171.3 (12) |
N2—H23N···Cl2 | 0.907 (15) | 2.234 (15) | 3.1201 (8) | 165.5 (13) |
C2—H2···Cl1 | 0.95 | 2.98 | 3.7487 (8) | 139 |
C6—H6···Cl2ii | 0.95 | 2.77 | 3.6055 (8) | 147 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+1; (iii) −x+1, −y+1, −z+2; (iv) −x+2, −y+1, −z+2. |