research papers
The crystal structure of a new crystalline phase, polymorph (II) of isobutyl-6-amino-5-cyano-2-methyl-4-phenyl-4H-pyran-3-carboxylate, was accurately determined by single-crystal X-ray diffraction analysis providing a clean identification of polymorphic forms. Comparison with a known phase, referred to as polymorph (I), reveals the type of supramolecular assembly. Inter- and intramolecular hydrogen-bonding interactions exhibit various supramolecular architectures in crystal packing and these variations confirm well the polymorphism in isobutyl-6-amino-5-cyano-2-methyl-4-phenyl-4H-pyran-3-carboxylate (IAPC) crystal structure. Crystal cohesion is achieved by N—HN, N—HO and C—HH—C interactions, responsible for the formation and strengthening of the supramolecular assembly. The objective of this investigation is to study crystalline forms which can offer enhanced physicochemical properties, and also to recognize the molecular orientations between such forms. The conformational polymorphs of IAPC were compared spectroscopically by FT–IR and FT–Raman. The bulk phases were studied by X-ray powder diffraction patterns. External morphology was investigated using scanning electron microscopic images. The molecular interactions were quantified using Hirshfeld surface and fingerprint analysis. Density functional theory (DFT) computations were used to optimize the structure. The optimized structure is further subjected to an analysis of Mulliken population, natural population and electrostatic potential.
Keywords: polymorphism; single-crystal X-ray diffraction; density functional theory; Hirshfeld surface analysis; fingerprint analysis.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520616003310/ao5008sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520616003310/ao5008Isup2.hkl |
CCDC reference: 1415778
Computing details top
Program(s) used to solve structure: olex2.solve (Bourhis et al., 2015); program(s) used to refine structure: olex2.refine (Bourhis et al., 2015); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).
(I) top
Crystal data top
C18H20N2O3 | V = 1681.3 (6) Å3 |
Mr = 312.37 | Z = 4 |
Triclinic, P1 | F(000) = 664.3291 |
a = 8.476 (2) Å | Dx = 1.234 Mg m−3 |
b = 9.923 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
c = 20.882 (4) Å | µ = 0.09 mm−1 |
α = 92.500 (3)° | T = 298 K |
β = 93.048 (3)° | Irregular, metallic light yellow |
γ = 106.171 (3)° | 0.3 × 0.3 × 0.25 mm |
Data collection top
Bruker SMART APEX2 area detector diffractometer | 4642 reflections with I ≥ 2u(I) |
Mirror optics monochromator | Rint = 0.020 |
Detector resolution: 7.9 pixels mm-1 | θmax = 25.1°, θmin = 2.0° |
ω and φ scans | h = −10→10 |
16201 measured reflections | k = −11→11 |
5928 independent reflections | l = −24→24 |
Refinement top
Refinement on F2 | 54 constraints |
Least-squares matrix: full | Primary atom site location: iterative |
R[F2 > 2σ(F2)] = 0.051 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.153 | w = 1/[σ2(Fo2) + (0.0857P)2 + 0.2381P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.002 |
5928 reflections | Δρmax = 0.27 e Å−3 |
450 parameters | Δρmin = −0.20 e Å−3 |
0 restraints |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.22832 (13) | 0.04944 (12) | 0.41244 (6) | 0.0598 (3) | |
O4 | 0.23466 (13) | 0.46130 (11) | 0.08914 (5) | 0.0550 (3) | |
O6 | 0.74684 (13) | 0.65187 (12) | 0.11778 (6) | 0.0633 (3) | |
O3 | −0.28717 (15) | −0.12147 (13) | 0.37996 (7) | 0.0690 (4) | |
O5 | 0.78504 (14) | 0.46669 (13) | 0.06377 (7) | 0.0675 (4) | |
N3 | 0.01605 (17) | 0.28742 (19) | 0.05364 (8) | 0.0598 (4) | |
C32 | 0.69416 (19) | 0.52614 (16) | 0.08693 (8) | 0.0499 (4) | |
C26 | 0.51356 (18) | 0.46122 (16) | 0.08494 (7) | 0.0477 (4) | |
C10 | 0.2885 (2) | 0.18631 (18) | 0.43473 (8) | 0.0555 (4) | |
O2 | −0.31207 (16) | 0.06117 (15) | 0.43901 (8) | 0.0865 (5) | |
C29 | 0.17958 (18) | 0.32637 (16) | 0.06310 (7) | 0.0483 (4) | |
C12 | −0.2270 (2) | 0.00064 (18) | 0.41258 (8) | 0.0544 (4) | |
N1 | 0.4517 (2) | 0.2204 (2) | 0.44599 (9) | 0.0738 (5) | |
C27 | 0.40173 (19) | 0.53128 (16) | 0.09205 (7) | 0.0502 (4) | |
C9 | 0.0598 (2) | −0.01534 (17) | 0.41103 (7) | 0.0523 (4) | |
C8 | −0.04693 (19) | 0.06146 (16) | 0.41239 (7) | 0.0499 (4) | |
C28 | 0.28590 (19) | 0.25141 (16) | 0.05089 (7) | 0.0496 (4) | |
N4 | 0.1920 (2) | 0.00941 (18) | −0.00895 (9) | 0.0815 (5) | |
C7 | 0.01004 (19) | 0.22009 (17) | 0.41534 (8) | 0.0506 (4) | |
C1 | −0.01373 (18) | 0.27654 (16) | 0.35009 (8) | 0.0507 (4) | |
C17 | 0.0321 (2) | −0.16961 (18) | 0.40864 (9) | 0.0647 (5) | |
H17a | 0.0484 (16) | −0.2022 (3) | 0.36621 (19) | 0.0970 (7)* | |
H17b | 0.1085 (11) | −0.1923 (2) | 0.4390 (5) | 0.0970 (7)* | |
H17c | −0.0784 (6) | −0.2144 (2) | 0.4192 (6) | 0.0970 (7)* | |
C33 | 0.9242 (2) | 0.71603 (19) | 0.12238 (9) | 0.0627 (5) | |
H33a | 0.9799 (2) | 0.65275 (19) | 0.14138 (9) | 0.0753 (6)* | |
H33b | 0.9629 (2) | 0.73520 (19) | 0.07991 (9) | 0.0753 (6)* | |
C6 | 0.0504 (2) | 0.22972 (19) | 0.29653 (9) | 0.0631 (5) | |
H6 | 0.1079 (2) | 0.16290 (19) | 0.30079 (9) | 0.0757 (5)* | |
C25 | 0.46600 (18) | 0.30330 (16) | 0.07443 (8) | 0.0490 (4) | |
H25 | 0.53085 (18) | 0.27996 (16) | 0.04035 (8) | 0.0588 (5)* | |
C30 | 0.23041 (19) | 0.11719 (18) | 0.01833 (8) | 0.0572 (4) | |
C11 | 0.1870 (2) | 0.26846 (18) | 0.44191 (8) | 0.0546 (4) | |
C24 | 0.4608 (2) | 0.27145 (19) | 0.19355 (9) | 0.0656 (5) | |
H24 | 0.4097 (2) | 0.34279 (19) | 0.19744 (9) | 0.0787 (6)* | |
C31 | 0.4211 (2) | 0.68381 (18) | 0.10370 (10) | 0.0698 (5) | |
H31a | 0.3363 (11) | 0.7092 (3) | 0.0789 (5) | 0.1047 (8)* | |
H31b | 0.4126 (17) | 0.7044 (3) | 0.14852 (15) | 0.1047 (8)* | |
H31c | 0.5270 (7) | 0.73645 (19) | 0.0912 (6) | 0.1047 (8)* | |
C34 | 0.9607 (2) | 0.84938 (18) | 0.16312 (9) | 0.0632 (5) | |
H34 | 0.9065 (2) | 0.91236 (18) | 0.14190 (9) | 0.0758 (6)* | |
C5 | 0.0308 (3) | 0.2802 (2) | 0.23722 (9) | 0.0743 (5) | |
H5 | 0.0742 (3) | 0.2470 (2) | 0.20185 (9) | 0.0892 (7)* | |
C19 | 0.50383 (18) | 0.23319 (16) | 0.13393 (9) | 0.0538 (4) | |
C13 | −0.4643 (2) | −0.1817 (2) | 0.37641 (10) | 0.0725 (5) | |
H13a | −0.4991 (2) | −0.2190 (2) | 0.41716 (10) | 0.0871 (6)* | |
H13b | −0.5189 (2) | −0.1104 (2) | 0.36680 (10) | 0.0871 (6)* | |
C18 | 0.2497 (2) | 0.4060 (2) | 0.47083 (10) | 0.0668 (5) | |
N2 | 0.2972 (2) | 0.5162 (2) | 0.49528 (11) | 0.1001 (7) | |
C23 | 0.4931 (3) | 0.2045 (2) | 0.24769 (11) | 0.0893 (7) | |
H23 | 0.4637 (3) | 0.2308 (2) | 0.28765 (11) | 0.1071 (9)* | |
C2 | −0.0972 (2) | 0.37666 (19) | 0.34204 (10) | 0.0670 (5) | |
H2 | −0.1415 (2) | 0.41036 (19) | 0.37702 (10) | 0.0804 (6)* | |
C3 | −0.1150 (3) | 0.4270 (2) | 0.28204 (12) | 0.0819 (6) | |
H3 | −0.1707 (3) | 0.4949 (2) | 0.27720 (12) | 0.0983 (8)* | |
C14 | −0.5085 (3) | −0.2970 (2) | 0.32439 (12) | 0.0908 (7) | |
H14 | −0.4605 (3) | −0.2579 (2) | 0.28520 (12) | 0.1089 (9)* | |
C22 | 0.5684 (3) | 0.0995 (3) | 0.24180 (17) | 0.1070 (10) | |
H22 | 0.5914 (3) | 0.0549 (3) | 0.27794 (17) | 0.1284 (12)* | |
C4 | −0.0521 (3) | 0.3786 (2) | 0.23015 (11) | 0.0782 (6) | |
H4 | −0.0656 (3) | 0.4126 (2) | 0.19002 (11) | 0.0939 (7)* | |
C35 | 0.8988 (3) | 0.8276 (3) | 0.22828 (10) | 0.0902 (7) | |
H35a | 0.7827 (5) | 0.7818 (16) | 0.22448 (10) | 0.1353 (10)* | |
H35b | 0.9548 (15) | 0.7702 (15) | 0.2508 (3) | 0.1353 (10)* | |
H35c | 0.9190 (19) | 0.9170 (3) | 0.2517 (3) | 0.1353 (10)* | |
C36 | 1.1457 (3) | 0.9180 (2) | 0.16670 (13) | 0.0954 (8) | |
H36a | 1.2011 (3) | 0.8590 (10) | 0.1884 (8) | 0.1431 (12)* | |
H36b | 1.1821 (5) | 0.9304 (18) | 0.12403 (13) | 0.1431 (12)* | |
H36c | 1.1707 (4) | 1.0079 (9) | 0.1899 (8) | 0.1431 (12)* | |
C20 | 0.5789 (2) | 0.12639 (19) | 0.12952 (12) | 0.0788 (6) | |
H20 | 0.6089 (2) | 0.09900 (19) | 0.08988 (12) | 0.0945 (7)* | |
C21 | 0.6096 (3) | 0.0604 (3) | 0.18341 (19) | 0.1081 (10) | |
H21 | 0.6592 (3) | −0.0120 (3) | 0.17975 (19) | 0.1298 (12)* | |
C15 | −0.4395 (5) | −0.4144 (4) | 0.3403 (3) | 0.1515 (19) | |
H15a | −0.507 (6) | −0.442 (5) | 0.373 (2) | 0.227 (3)* | |
H15b | −0.473 (6) | −0.483 (5) | 0.311 (2) | 0.227 (3)* | |
C16 | −0.6912 (3) | −0.3463 (4) | 0.31132 (17) | 0.1325 (12) | |
H16a | −0.7413 (4) | −0.386 (3) | 0.3490 (5) | 0.1987 (18)* | |
H16b | −0.7313 (5) | −0.2683 (7) | 0.3003 (13) | 0.1987 (18)* | |
H16c | −0.7184 (4) | −0.417 (2) | 0.2763 (9) | 0.1987 (18)* | |
H3a | −0.034 (2) | 0.201 (2) | 0.0423 (9) | 0.061 (5)* | |
H3b | −0.035 (2) | 0.3532 (19) | 0.0557 (8) | 0.055 (5)* | |
H1a | 0.508 (3) | 0.305 (2) | 0.4590 (10) | 0.079 (7)* | |
H1b | 0.500 (2) | 0.153 (2) | 0.4441 (9) | 0.063 (5)* | |
H15c | −0.325 (5) | −0.376 (4) | 0.3509 (18) | 0.189 (16)* | |
H7 | −0.052 (2) | 0.2553 (17) | 0.4433 (8) | 0.055 (5)* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0443 (6) | 0.0604 (7) | 0.0735 (8) | 0.0159 (5) | −0.0026 (5) | −0.0084 (6) |
O4 | 0.0424 (6) | 0.0519 (6) | 0.0676 (7) | 0.0112 (5) | 0.0010 (5) | −0.0142 (5) |
O6 | 0.0419 (6) | 0.0579 (7) | 0.0800 (8) | 0.0009 (5) | 0.0020 (5) | −0.0183 (6) |
O3 | 0.0479 (7) | 0.0634 (8) | 0.0870 (9) | 0.0056 (6) | −0.0007 (6) | −0.0176 (6) |
O5 | 0.0445 (7) | 0.0594 (7) | 0.0956 (9) | 0.0115 (5) | 0.0084 (6) | −0.0108 (6) |
N3 | 0.0418 (8) | 0.0564 (9) | 0.0774 (10) | 0.0118 (7) | −0.0035 (7) | −0.0138 (8) |
C32 | 0.0432 (9) | 0.0477 (9) | 0.0548 (9) | 0.0074 (7) | 0.0011 (7) | −0.0012 (7) |
C26 | 0.0435 (8) | 0.0461 (8) | 0.0492 (8) | 0.0070 (7) | 0.0010 (6) | −0.0057 (7) |
C10 | 0.0472 (9) | 0.0619 (10) | 0.0540 (9) | 0.0125 (8) | −0.0035 (7) | −0.0060 (8) |
O2 | 0.0484 (7) | 0.0755 (9) | 0.1296 (13) | 0.0117 (6) | 0.0111 (7) | −0.0275 (8) |
C29 | 0.0433 (8) | 0.0499 (9) | 0.0474 (8) | 0.0085 (7) | −0.0014 (6) | −0.0077 (7) |
C12 | 0.0481 (9) | 0.0540 (9) | 0.0595 (10) | 0.0127 (8) | 0.0013 (7) | −0.0003 (8) |
N1 | 0.0455 (9) | 0.0712 (11) | 0.1014 (13) | 0.0166 (9) | −0.0110 (8) | −0.0130 (10) |
C27 | 0.0443 (9) | 0.0477 (9) | 0.0542 (9) | 0.0080 (7) | 0.0006 (7) | −0.0071 (7) |
C9 | 0.0480 (9) | 0.0578 (10) | 0.0486 (9) | 0.0126 (7) | −0.0008 (7) | −0.0022 (7) |
C8 | 0.0455 (9) | 0.0533 (9) | 0.0482 (8) | 0.0109 (7) | 0.0006 (6) | −0.0022 (7) |
C28 | 0.0426 (8) | 0.0476 (8) | 0.0541 (9) | 0.0083 (7) | −0.0032 (6) | −0.0099 (7) |
N4 | 0.0583 (9) | 0.0670 (10) | 0.1098 (13) | 0.0110 (8) | −0.0072 (9) | −0.0391 (10) |
C7 | 0.0412 (8) | 0.0532 (9) | 0.0557 (9) | 0.0128 (7) | 0.0015 (7) | −0.0097 (7) |
C1 | 0.0384 (8) | 0.0442 (8) | 0.0642 (10) | 0.0052 (6) | −0.0037 (7) | −0.0039 (7) |
C17 | 0.0646 (11) | 0.0588 (10) | 0.0711 (12) | 0.0202 (8) | −0.0037 (9) | −0.0002 (8) |
C33 | 0.0417 (9) | 0.0643 (11) | 0.0719 (11) | −0.0007 (8) | 0.0046 (8) | −0.0060 (9) |
C6 | 0.0674 (11) | 0.0612 (10) | 0.0631 (11) | 0.0235 (9) | −0.0001 (8) | −0.0003 (8) |
C25 | 0.0373 (8) | 0.0473 (8) | 0.0590 (9) | 0.0087 (6) | 0.0018 (6) | −0.0123 (7) |
C30 | 0.0405 (8) | 0.0579 (10) | 0.0690 (11) | 0.0112 (7) | −0.0048 (7) | −0.0148 (8) |
C11 | 0.0451 (9) | 0.0593 (10) | 0.0546 (9) | 0.0100 (7) | −0.0034 (7) | −0.0096 (7) |
C24 | 0.0614 (11) | 0.0562 (10) | 0.0711 (12) | 0.0063 (8) | −0.0093 (9) | 0.0014 (9) |
C31 | 0.0612 (11) | 0.0501 (10) | 0.0964 (14) | 0.0158 (8) | 0.0011 (10) | −0.0104 (9) |
C34 | 0.0535 (10) | 0.0538 (10) | 0.0744 (11) | 0.0042 (8) | −0.0024 (8) | −0.0012 (8) |
C5 | 0.0828 (14) | 0.0762 (13) | 0.0611 (11) | 0.0182 (11) | 0.0013 (10) | 0.0058 (10) |
C19 | 0.0359 (8) | 0.0421 (8) | 0.0763 (11) | 0.0029 (6) | −0.0080 (7) | −0.0047 (7) |
C13 | 0.0469 (10) | 0.0686 (12) | 0.0936 (14) | 0.0051 (8) | −0.0021 (9) | −0.0062 (10) |
C18 | 0.0461 (9) | 0.0722 (12) | 0.0762 (12) | 0.0122 (9) | −0.0067 (8) | −0.0181 (10) |
N2 | 0.0687 (11) | 0.0840 (13) | 0.1336 (17) | 0.0103 (10) | −0.0144 (11) | −0.0466 (12) |
C23 | 0.0855 (15) | 0.0784 (14) | 0.0819 (15) | −0.0101 (12) | −0.0187 (12) | 0.0128 (12) |
C2 | 0.0553 (10) | 0.0580 (10) | 0.0901 (14) | 0.0204 (8) | 0.0044 (9) | 0.0030 (9) |
C3 | 0.0690 (13) | 0.0664 (12) | 0.1152 (18) | 0.0260 (10) | −0.0027 (12) | 0.0230 (12) |
C14 | 0.0627 (13) | 0.0856 (15) | 0.1069 (18) | −0.0022 (11) | 0.0021 (11) | −0.0236 (13) |
C22 | 0.0895 (18) | 0.0728 (16) | 0.137 (2) | −0.0072 (13) | −0.0464 (17) | 0.0365 (16) |
C4 | 0.0704 (13) | 0.0756 (13) | 0.0814 (14) | 0.0083 (10) | −0.0072 (10) | 0.0217 (11) |
C35 | 0.0879 (15) | 0.0946 (16) | 0.0765 (14) | 0.0096 (12) | 0.0029 (11) | −0.0129 (12) |
C36 | 0.0643 (13) | 0.0711 (13) | 0.129 (2) | −0.0124 (11) | 0.0035 (12) | −0.0197 (13) |
C20 | 0.0547 (11) | 0.0557 (11) | 0.1248 (18) | 0.0176 (9) | −0.0081 (11) | −0.0034 (11) |
C21 | 0.0765 (16) | 0.0639 (14) | 0.181 (3) | 0.0205 (12) | −0.0353 (18) | 0.0213 (18) |
C15 | 0.093 (2) | 0.087 (2) | 0.266 (6) | 0.0235 (18) | 0.000 (3) | −0.053 (3) |
C16 | 0.0742 (16) | 0.139 (3) | 0.158 (3) | −0.0026 (16) | −0.0126 (16) | −0.046 (2) |
Geometric parameters (Å, º) top
O1—C10 | 1.362 (2) | C11—C18 | 1.414 (2) |
O1—C9 | 1.3919 (19) | C24—H24 | 0.9300 |
O4—C29 | 1.3666 (18) | C24—C19 | 1.383 (3) |
O4—C27 | 1.3895 (18) | C24—C23 | 1.388 (3) |
O6—C32 | 1.3266 (19) | C31—H31a | 0.9600 |
O6—C33 | 1.4566 (19) | C31—H31b | 0.9600 |
O3—C12 | 1.319 (2) | C31—H31c | 0.9600 |
O3—C13 | 1.450 (2) | C34—H34 | 0.9800 |
O5—C32 | 1.2013 (19) | C34—C35 | 1.487 (3) |
N3—C29 | 1.332 (2) | C34—C36 | 1.522 (3) |
N3—H3a | 0.859 (19) | C5—H5 | 0.9300 |
N3—H3b | 0.878 (19) | C5—C4 | 1.361 (3) |
C32—C26 | 1.484 (2) | C19—C20 | 1.382 (2) |
C26—C27 | 1.333 (2) | C13—H13a | 0.9700 |
C26—C25 | 1.508 (2) | C13—H13b | 0.9700 |
C10—N1 | 1.335 (2) | C13—C14 | 1.496 (3) |
C10—C11 | 1.349 (2) | C18—N2 | 1.141 (2) |
O2—C12 | 1.200 (2) | C23—H23 | 0.9300 |
C29—C28 | 1.346 (2) | C23—C22 | 1.370 (4) |
C12—C8 | 1.477 (2) | C2—H2 | 0.9300 |
N1—H1a | 0.86 (2) | C2—C3 | 1.385 (3) |
N1—H1b | 0.88 (2) | C3—H3 | 0.9300 |
C27—C31 | 1.484 (2) | C3—C4 | 1.359 (3) |
C9—C8 | 1.336 (2) | C14—H14 | 0.9800 |
C9—C17 | 1.481 (2) | C14—C15 | 1.485 (5) |
C8—C7 | 1.510 (2) | C14—C16 | 1.495 (3) |
C28—C25 | 1.516 (2) | C22—H22 | 0.9300 |
C28—C30 | 1.413 (2) | C22—C21 | 1.356 (4) |
N4—C30 | 1.143 (2) | C4—H4 | 0.9300 |
C7—C1 | 1.520 (2) | C35—H35a | 0.9600 |
C7—C11 | 1.508 (2) | C35—H35b | 0.9600 |
C7—H7 | 0.926 (17) | C35—H35c | 0.9600 |
C1—C6 | 1.387 (2) | C36—H36a | 0.9600 |
C1—C2 | 1.381 (2) | C36—H36b | 0.9600 |
C17—H17a | 0.9600 | C36—H36c | 0.9600 |
C17—H17b | 0.9600 | C20—H20 | 0.9300 |
C17—H17c | 0.9600 | C20—C21 | 1.375 (4) |
C33—H33a | 0.9700 | C21—H21 | 0.9300 |
C33—H33b | 0.9700 | C15—H15a | 0.91 (5) |
C33—C34 | 1.489 (2) | C15—H15b | 0.87 (4) |
C6—H6 | 0.9300 | C15—H15c | 0.95 (4) |
C6—C5 | 1.375 (3) | C16—H16a | 0.9600 |
C25—H25 | 0.9800 | C16—H16b | 0.9600 |
C25—C19 | 1.513 (2) | C16—H16c | 0.9600 |
C9—O1—C10 | 119.46 (12) | H31b—C31—C27 | 109.5 |
C27—O4—C29 | 119.78 (12) | H31b—C31—H31a | 109.5 |
C33—O6—C32 | 116.06 (13) | H31c—C31—C27 | 109.5 |
C13—O3—C12 | 117.09 (14) | H31c—C31—H31a | 109.5 |
H3a—N3—C29 | 118.8 (12) | H31c—C31—H31b | 109.5 |
H3b—N3—C29 | 117.9 (11) | H34—C34—C33 | 108.13 (11) |
H3b—N3—H3a | 123.0 (17) | C35—C34—C33 | 112.66 (16) |
O5—C32—O6 | 123.09 (14) | C35—C34—H34 | 108.13 (13) |
C26—C32—O6 | 114.88 (13) | C36—C34—C33 | 108.27 (16) |
C26—C32—O5 | 122.00 (14) | C36—C34—H34 | 108.13 (12) |
C27—C26—C32 | 125.15 (14) | C36—C34—C35 | 111.36 (18) |
C25—C26—C32 | 112.81 (13) | H5—C5—C6 | 119.91 (12) |
C25—C26—C27 | 122.04 (13) | C4—C5—C6 | 120.2 (2) |
N1—C10—O1 | 110.65 (16) | C4—C5—H5 | 119.91 (13) |
C11—C10—O1 | 120.76 (14) | C24—C19—C25 | 121.14 (15) |
C11—C10—N1 | 128.58 (17) | C20—C19—C25 | 120.44 (18) |
N3—C29—O4 | 110.55 (14) | C20—C19—C24 | 118.40 (19) |
C28—C29—O4 | 120.74 (13) | H13a—C13—O3 | 110.13 (10) |
C28—C29—N3 | 128.70 (15) | H13b—C13—O3 | 110.13 (10) |
O2—C12—O3 | 122.87 (15) | H13b—C13—H13a | 108.4 |
C8—C12—O3 | 115.31 (14) | C14—C13—O3 | 107.87 (16) |
C8—C12—O2 | 121.78 (15) | C14—C13—H13a | 110.13 (13) |
H1a—N1—C10 | 121.2 (15) | C14—C13—H13b | 110.13 (13) |
H1b—N1—C10 | 118.3 (12) | N2—C18—C11 | 178.2 (2) |
H1b—N1—H1a | 120.1 (19) | H23—C23—C24 | 120.25 (15) |
C26—C27—O4 | 121.07 (13) | C22—C23—C24 | 119.5 (3) |
C31—C27—O4 | 108.07 (13) | C22—C23—H23 | 120.25 (18) |
C31—C27—C26 | 130.86 (15) | H2—C2—C1 | 119.87 (11) |
C8—C9—O1 | 120.55 (15) | C3—C2—C1 | 120.25 (19) |
C17—C9—O1 | 108.71 (14) | C3—C2—H2 | 119.87 (13) |
C17—C9—C8 | 130.73 (15) | H3—C3—C2 | 119.56 (13) |
C9—C8—C12 | 123.74 (15) | C4—C3—C2 | 120.88 (19) |
C7—C8—C12 | 114.65 (13) | C4—C3—H3 | 119.56 (12) |
C7—C8—C9 | 121.60 (14) | H14—C14—C13 | 107.82 (13) |
C25—C28—C29 | 121.74 (13) | C15—C14—C13 | 111.7 (3) |
C30—C28—C29 | 120.54 (14) | C15—C14—H14 | 107.8 (2) |
C30—C28—C25 | 117.63 (13) | C16—C14—C13 | 109.9 (2) |
C1—C7—C8 | 111.50 (13) | C16—C14—H14 | 107.82 (18) |
C11—C7—C8 | 108.79 (13) | C16—C14—C15 | 111.7 (2) |
C11—C7—C1 | 112.21 (13) | H22—C22—C23 | 119.92 (18) |
H7—C7—C8 | 109.3 (10) | C21—C22—C23 | 120.2 (2) |
H7—C7—C1 | 107.2 (10) | C21—C22—H22 | 119.92 (16) |
H7—C7—C11 | 107.8 (10) | C3—C4—C5 | 119.7 (2) |
C6—C1—C7 | 120.52 (14) | H4—C4—C5 | 120.16 (13) |
C2—C1—C7 | 121.73 (16) | H4—C4—C3 | 120.16 (12) |
C2—C1—C6 | 117.75 (17) | H35a—C35—C34 | 109.5 |
H17a—C17—C9 | 109.5 | H35b—C35—C34 | 109.5 |
H17b—C17—C9 | 109.5 | H35b—C35—H35a | 109.5 |
H17b—C17—H17a | 109.5 | H35c—C35—C34 | 109.5 |
H17c—C17—C9 | 109.5 | H35c—C35—H35a | 109.5 |
H17c—C17—H17a | 109.5 | H35c—C35—H35b | 109.5 |
H17c—C17—H17b | 109.5 | H36a—C36—C34 | 109.5 |
H33a—C33—O6 | 110.04 (9) | H36b—C36—C34 | 109.5 |
H33b—C33—O6 | 110.04 (9) | H36b—C36—H36a | 109.5 |
H33b—C33—H33a | 108.4 | H36c—C36—C34 | 109.5 |
C34—C33—O6 | 108.30 (14) | H36c—C36—H36a | 109.5 |
C34—C33—H33a | 110.04 (11) | H36c—C36—H36b | 109.5 |
C34—C33—H33b | 110.04 (10) | H20—C20—C19 | 119.80 (13) |
H6—C6—C1 | 119.37 (10) | C21—C20—C19 | 120.4 (2) |
C5—C6—C1 | 121.26 (18) | C21—C20—H20 | 119.80 (18) |
C5—C6—H6 | 119.37 (12) | C20—C21—C22 | 120.8 (2) |
C28—C25—C26 | 108.86 (13) | H21—C21—C22 | 119.59 (16) |
H25—C25—C26 | 107.79 (8) | H21—C21—C20 | 119.59 (18) |
H25—C25—C28 | 107.79 (8) | H15a—C15—C14 | 94 (3) |
C19—C25—C26 | 112.11 (12) | H15b—C15—C14 | 110 (3) |
C19—C25—C28 | 112.29 (13) | H15b—C15—H15a | 103 (4) |
C19—C25—H25 | 107.79 (9) | H15c—C15—C14 | 108 (2) |
N4—C30—C28 | 177.11 (18) | H15c—C15—H15a | 118 (4) |
C7—C11—C10 | 121.08 (14) | H15c—C15—H15b | 119 (4) |
C18—C11—C10 | 119.69 (15) | H16a—C16—C14 | 109.5 |
C18—C11—C7 | 119.09 (15) | H16b—C16—C14 | 109.5 |
C19—C24—H24 | 119.64 (11) | H16b—C16—H16a | 109.5 |
C23—C24—H24 | 119.64 (15) | H16c—C16—C14 | 109.5 |
C23—C24—C19 | 120.7 (2) | H16c—C16—H16a | 109.5 |
H31a—C31—C27 | 109.5 | H16c—C16—H16b | 109.5 |