Experimental electron density analysis by means of high-resolution X-ray diffraction data up to sinθ/λ
max = 1.11 Å
−1 at 100 (1) K has been performed to analyze the detailed structure and the strength of intermolecular interactions responsible for the formation of a new solid form of nicotinic acid (NA), cocrystallized with pyrogallol (PY). There are two NA–PY units in the asymmetric unit. The experimental results are compared with the results obtained from theoretical structure factors modeled using periodic boundary DFT calculations. Both refinements were carried out using the Hansen and Coppens multipolar formalism (in
MoPro program). The non-centrosymmetric and polar nature of the crystal system rendered the multipolar refinement challenging which was addressed by involving the transferability principle. This study highlights the significance of the transferability principle in electron density modeling in non-routine situations. The 2:2 cocrystal of NA–PY exhibits a zigzag, brickwall and sheet-like layered structure in three dimensions and is stabilized by strong intra- and inter-molecular hydrogen bonding through N—H
O and O—H
O bonds, some of them due to the zwitterion nature of NA as well as weak interactions between the PY molecules. Ranking these interactions via topological analysis of the electron density shows the leading role of the NA–NA substructure which drives the organization of the cocrystals. These strong interactions between the NA zwitterions may explain why
Z′ = 2.
Supporting information
CCDC references: 2107343; 2107344; 2107345
Program(s) used to solve structure: SHELXT 2014/5 (Sheldrick, 2014) for IAM_SHELX. Program(s) used to refine structure: MoPro (J. Appl. Cryst. 2005, 38, 38-54) for IAM_MoPro, multipolar_MoPro, theoretical; XL (Sheldrick, 2008) for IAM_SHELX. Molecular graphics: Olex2 (Dolomanov et al., 2009) for IAM_SHELX. Software used to prepare material for publication: Olex2 (Dolomanov et al., 2009) for IAM_SHELX.
Crystal data top
C6H5NO2·C6H6O3 | Dx = 1.566 Mg m−3 |
Mr = 249.22 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pca21 | Cell parameters from 2780 reflections |
a = 13.6648 (4) Å | θ = 2.3–52.2° |
b = 11.9321 (3) Å | µ = 0.12 mm−1 |
c = 12.9678 (4) Å | T = 100 K |
V = 2114.40 (10) Å3 | Block, brown |
Z = 8 | 0.35 × 0.29 × 0.24 mm |
F(000) = 1040 | |
Data collection top
Bruker D8 Venture PHOTON II diffractometer | 19169 reflections with > 2.0 σ(I) |
Radiation source: Micro-focus | Rint = 0.051 |
ω and phi scan | θmax = 52.2°, θmin = 2.3° |
Absorption correction: analytical SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0673 before and 0.0563 after correction.
The Ratio of minimum to maximum transmission is 0.8999.
The λ/2 correction factor is Not present. | h = −30→21 |
Tmin = 0.675, Tmax = 0.750 | k = −26→24 |
24508 measured reflections | l = −28→28 |
19169 independent reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.064 | w = 1/[1.044*σ2(Fo2) + 0.0054*Yo2] |
S = 1.08 | (Δ/σ)max = 0.062 |
19169 reflections | Δρmax = 0.70 e Å−3 |
325 parameters | Δρmin = −0.51 e Å−3 |
0 restraints | Absolute structure: Rogers (1981), 8469 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Rogers parameter: 1 |
Special details top
Refinement. Refinement of F2 against reflections.
The threshold expression of F2 > 2sigma(F2) is
used for calculating R-factors(gt) and is not
relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice
as large as those based on F, and R-factors based on
ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.68086 (4) | 0.64334 (5) | 0.547657 (10) | 0.01537 (2) | |
N1 | 0.68878 (4) | 0.35059 (4) | 0.37560 (6) | 0.01156 (2) | |
H1 | 0.68602 | 0.27497 | 0.41133 | 0.02558 | |
C1 | 0.68304 (4) | 0.44404 (5) | 0.43321 (6) | 0.01069 (2) | |
H1A | 0.67533 | 0.43767 | 0.51612 | 0.02649 | |
O2 | 0.68743 (5) | 0.74549 (5) | 0.40295 (6) | 0.01747 (2) | |
N2 | 0.67958 (4) | −0.14702 (5) | 0.62877 (6) | 0.01136 (2) | |
H2 | 0.67978 | −0.22211 | 0.59199 | 0.02593 | |
C2 | 0.68697 (4) | 0.54854 (5) | 0.38668 (6) | 0.01017 (2) | |
O3 | 0.68257 (4) | 0.14659 (4) | 0.45986 (5) | 0.01527 (2) | |
C3 | 0.69543 (5) | 0.55387 (5) | 0.27945 (7) | 0.01227 (2) | |
H3 | 0.69739 | 0.63461 | 0.24135 | 0.02621 | |
O4 | 0.67781 (4) | 0.24890 (5) | 0.60435 (6) | 0.01594 (2) | |
C4 | 0.70137 (5) | 0.45585 (6) | 0.22167 (7) | 0.01336 (2) | |
H4 | 0.70843 | 0.45916 | 0.13854 | 0.02551 | |
C5 | 0.69804 (5) | 0.35394 (5) | 0.27265 (7) | 0.01292 (2) | |
H5 | 0.70291 | 0.27660 | 0.22924 | 0.02345 | |
O5 | 0.56140 (4) | 0.40688 (4) | 0.68618 (6) | 0.01504 (2) | |
H5A | 0.59802 | 0.33631 | 0.68852 | 0.02559 | |
O6 | 0.58033 (4) | 0.28203 (4) | 0.86706 (6) | 0.01667 (2) | |
H6 | 0.57819 | 0.24930 | 0.93633 | 0.02326 | |
C6 | 0.68415 (5) | 0.65410 (5) | 0.45040 (7) | 0.01160 (2) | |
C7 | 0.67999 (5) | −0.05243 (5) | 0.57228 (6) | 0.01110 (2) | |
H7 | 0.68164 | −0.05748 | 0.48891 | 0.02381 | |
O7 | 0.54114 (4) | 0.63229 (4) | 0.69501 (6) | 0.01416 (2) | |
H7A | 0.58089 | 0.59771 | 0.64075 | 0.02620 | |
O8 | 0.57053 (4) | 1.13640 (4) | 0.28397 (6) | 0.01463 (2) | |
H8 | 0.60255 | 1.10762 | 0.34619 | 0.02487 | |
C8 | 0.67814 (4) | 0.05134 (5) | 0.62073 (6) | 0.01012 (2) | |
C9 | 0.67581 (5) | 0.05484 (5) | 0.72827 (7) | 0.01201 (2) | |
H9 | 0.67254 | 0.13476 | 0.76771 | 0.02486 | |
O9 | 0.54926 (4) | 1.19674 (5) | 0.07979 (6) | 0.01550 (2) | |
H9A | 0.52831 | 1.24072 | 0.13967 | 0.02641 | |
C10 | 0.67769 (5) | −0.04451 (5) | 0.78492 (7) | 0.01266 (2) | |
H10 | 0.67795 | −0.04250 | 0.86841 | 0.02400 | |
O10 | 0.58565 (4) | 0.91944 (4) | 0.33841 (6) | 0.01431 (2) | |
H10A | 0.61352 | 0.84449 | 0.34804 | 0.02639 | |
C11 | 0.67913 (5) | −0.14542 (5) | 0.73257 (7) | 0.01223 (2) | |
H11 | 0.67991 | −0.22346 | 0.77522 | 0.02658 | |
C12 | 0.67900 (5) | 0.15763 (5) | 0.55721 (7) | 0.01127 (2) | |
C13 | 0.56224 (4) | 0.45555 (5) | 0.78110 (7) | 0.01050 (2) | |
C14 | 0.57031 (4) | 0.39610 (5) | 0.87395 (7) | 0.01132 (2) | |
C15 | 0.56852 (5) | 0.45306 (6) | 0.96802 (7) | 0.01318 (2) | |
H15 | 0.57585 | 0.40694 | 1.03954 | 0.02636 | |
C16 | 0.55728 (5) | 0.56925 (6) | 0.97010 (7) | 0.01411 (3) | |
H16 | 0.55545 | 0.61300 | 1.04324 | 0.02659 | |
C17 | 0.54835 (5) | 0.62906 (5) | 0.87836 (7) | 0.01290 (2) | |
H17 | 0.53926 | 0.71921 | 0.87983 | 0.02712 | |
C18 | 0.55112 (4) | 0.57223 (5) | 0.78478 (7) | 0.01057 (2) | |
C19 | 0.56861 (4) | 1.05463 (5) | 0.21022 (6) | 0.01017 (2) | |
C20 | 0.55772 (4) | 1.08576 (5) | 0.10733 (7) | 0.01098 (2) | |
C21 | 0.55609 (5) | 1.00464 (6) | 0.02978 (7) | 0.01425 (3) | |
H21 | 0.54768 | 1.02901 | −0.05018 | 0.02647 | |
C22 | 0.56525 (5) | 0.89210 (6) | 0.05631 (7) | 0.01582 (3) | |
H22 | 0.56529 | 0.82899 | −0.00371 | 0.02600 | |
C23 | 0.57457 (5) | 0.85924 (5) | 0.15926 (7) | 0.01369 (2) | |
H23 | 0.58033 | 0.77133 | 0.17915 | 0.02656 | |
C24 | 0.57653 (4) | 0.94088 (5) | 0.23588 (7) | 0.01049 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0243 (2) | 0.01114 (17) | 0.01064 (17) | −0.00074 (14) | 0.00434 (15) | −0.00181 (13) |
N1 | 0.01403 (16) | 0.00894 (16) | 0.01171 (17) | −0.00040 (12) | 0.00030 (14) | −0.00081 (13) |
H1 | 0.03895 | 0.01701 | 0.02077 | 0.00008 | 0.00127 | 0.00250 |
C1 | 0.01405 (19) | 0.00871 (18) | 0.00931 (17) | 0.00010 (14) | 0.00013 (14) | −0.00005 (14) |
H1A | 0.03980 | 0.02492 | 0.01473 | 0.00040 | 0.00213 | 0.00041 |
O2 | 0.0267 (2) | 0.00858 (16) | 0.0171 (2) | 0.00236 (15) | 0.00211 (17) | 0.00226 (14) |
N2 | 0.01452 (18) | 0.00911 (16) | 0.01043 (17) | 0.00083 (13) | 0.00008 (13) | 0.00020 (13) |
H2 | 0.03877 | 0.01714 | 0.02187 | −0.00073 | −0.00055 | −0.00296 |
C2 | 0.01268 (17) | 0.00885 (17) | 0.00897 (17) | 0.00076 (13) | 0.00055 (13) | 0.00032 (13) |
O3 | 0.0261 (2) | 0.01096 (17) | 0.00878 (15) | −0.00198 (15) | −0.00167 (14) | 0.00048 (12) |
C3 | 0.01538 (19) | 0.0117 (2) | 0.00973 (18) | −0.00020 (15) | 0.00025 (16) | 0.00120 (15) |
H3 | 0.03908 | 0.01726 | 0.02229 | 0.00049 | 0.00065 | 0.00380 |
O4 | 0.0258 (2) | 0.00874 (15) | 0.01332 (17) | −0.00051 (15) | 0.00021 (15) | −0.00238 (13) |
C4 | 0.0160 (2) | 0.0147 (2) | 0.00942 (18) | −0.00140 (17) | 0.00121 (16) | −0.00154 (16) |
H4 | 0.03677 | 0.02522 | 0.01455 | 0.00046 | 0.00126 | 0.00000 |
C5 | 0.01462 (19) | 0.0124 (2) | 0.0117 (2) | −0.00106 (15) | 0.00122 (15) | −0.00260 (16) |
H5 | 0.03025 | 0.01899 | 0.02110 | 0.00494 | −0.00072 | −0.00064 |
O5 | 0.0237 (2) | 0.01214 (16) | 0.00931 (15) | 0.00291 (14) | −0.00265 (14) | −0.00175 (13) |
H5A | 0.03699 | 0.01790 | 0.02187 | 0.00093 | 0.00087 | −0.00484 |
O6 | 0.0253 (2) | 0.01035 (16) | 0.01441 (18) | −0.00019 (15) | −0.00086 (16) | 0.00238 (14) |
H6 | 0.03171 | 0.02153 | 0.01654 | 0.00030 | 0.00123 | 0.00207 |
C6 | 0.01474 (19) | 0.00867 (18) | 0.01138 (19) | 0.00103 (14) | 0.00199 (15) | −0.00032 (14) |
C7 | 0.0148 (2) | 0.00941 (18) | 0.00906 (17) | −0.00002 (14) | −0.00041 (14) | −0.00050 (14) |
H7 | 0.03050 | 0.02259 | 0.01834 | 0.00474 | 0.00370 | −0.00120 |
O7 | 0.02105 (19) | 0.01195 (16) | 0.00948 (15) | 0.00349 (14) | 0.00309 (13) | 0.00212 (12) |
H7A | 0.03827 | 0.02492 | 0.01542 | −0.00022 | 0.00007 | −0.00079 |
O8 | 0.0244 (2) | 0.00914 (15) | 0.01038 (15) | 0.00040 (13) | −0.00383 (15) | −0.00146 (13) |
H8 | 0.03440 | 0.02145 | 0.01874 | 0.00412 | −0.00433 | 0.00058 |
C8 | 0.01295 (18) | 0.00882 (17) | 0.00858 (17) | −0.00023 (14) | −0.00049 (13) | −0.00023 (13) |
C9 | 0.0157 (2) | 0.01124 (19) | 0.00905 (18) | −0.00025 (15) | 0.00012 (15) | −0.00124 (15) |
H9 | 0.03523 | 0.02041 | 0.01895 | 0.00352 | 0.00206 | −0.00199 |
O9 | 0.0228 (2) | 0.01210 (17) | 0.01160 (16) | 0.00234 (15) | 0.00050 (14) | 0.00303 (13) |
H9A | 0.03903 | 0.01756 | 0.02263 | 0.00032 | 0.00076 | −0.00407 |
C10 | 0.0158 (2) | 0.0134 (2) | 0.00884 (17) | 0.00060 (15) | 0.00067 (15) | 0.00079 (16) |
H10 | 0.03339 | 0.01774 | 0.02085 | 0.00506 | −0.00027 | 0.00034 |
O10 | 0.02229 (19) | 0.01115 (16) | 0.00950 (15) | 0.00196 (14) | 0.00033 (14) | 0.00129 (12) |
H10A | 0.03845 | 0.02538 | 0.01535 | −0.00071 | 0.00009 | 0.00011 |
C11 | 0.01425 (19) | 0.01153 (19) | 0.0109 (2) | 0.00115 (15) | 0.00053 (15) | 0.00190 (15) |
H11 | 0.03862 | 0.01788 | 0.02324 | −0.00089 | −0.00043 | 0.00466 |
C12 | 0.01537 (19) | 0.00888 (18) | 0.00957 (17) | −0.00059 (14) | −0.00136 (15) | −0.00045 (14) |
C13 | 0.01265 (17) | 0.01040 (18) | 0.00845 (16) | 0.00014 (13) | −0.00084 (14) | −0.00005 (14) |
C14 | 0.01310 (18) | 0.01128 (18) | 0.00959 (17) | −0.00047 (14) | −0.00041 (14) | 0.00160 (15) |
C15 | 0.0156 (2) | 0.0154 (2) | 0.00860 (18) | −0.00070 (17) | −0.00002 (15) | 0.00107 (16) |
H15 | 0.03769 | 0.02408 | 0.01731 | 0.00164 | −0.00069 | 0.00415 |
C16 | 0.0173 (2) | 0.0161 (2) | 0.00891 (18) | −0.00026 (17) | 0.00134 (16) | −0.00136 (16) |
H16 | 0.03836 | 0.02448 | 0.01693 | 0.00192 | 0.00020 | −0.00470 |
C17 | 0.0160 (2) | 0.01226 (19) | 0.01043 (18) | 0.00023 (16) | 0.00197 (16) | −0.00155 (16) |
H17 | 0.04021 | 0.01660 | 0.02457 | 0.00338 | −0.00003 | −0.00083 |
C18 | 0.01268 (17) | 0.01020 (17) | 0.00883 (16) | 0.00045 (14) | 0.00112 (14) | 0.00006 (14) |
C19 | 0.01243 (17) | 0.00948 (17) | 0.00861 (17) | 0.00009 (13) | −0.00086 (13) | −0.00036 (13) |
C20 | 0.01230 (17) | 0.01156 (19) | 0.00907 (16) | 0.00131 (15) | −0.00070 (14) | 0.00055 (15) |
C21 | 0.0170 (2) | 0.0166 (2) | 0.00916 (18) | 0.00398 (18) | −0.00117 (15) | −0.00189 (16) |
H21 | 0.03813 | 0.02520 | 0.01608 | 0.00221 | −0.00174 | 0.00266 |
C22 | 0.0200 (2) | 0.0153 (2) | 0.0121 (2) | 0.00426 (19) | −0.00217 (18) | −0.00439 (18) |
H22 | 0.03732 | 0.02102 | 0.01965 | 0.00179 | −0.00033 | −0.00504 |
C23 | 0.0174 (2) | 0.0108 (2) | 0.0129 (2) | 0.00195 (16) | −0.00102 (17) | −0.00289 (16) |
H23 | 0.03935 | 0.01617 | 0.02415 | 0.00233 | −0.00057 | 0.00205 |
C24 | 0.01267 (17) | 0.00932 (17) | 0.00948 (17) | 0.00018 (14) | 0.00001 (14) | −0.00048 (14) |
Geometric parameters (Å, º) top
O1—C6 | 1.2685 (9) | C8—C12 | 1.5123 (8) |
N1—C1 | 1.3444 (8) | C8—C9 | 1.3956 (8) |
N1—C5 | 1.3416 (9) | C9—C10 | 1.3948 (9) |
N1—H1 | 1.0150 | C9—H9 | 1.0830 |
C1—C2 | 1.3863 (8) | O9—C20 | 1.3763 (8) |
C1—H1A | 1.0830 | O9—H9A | 0.9800 |
O2—C6 | 1.2529 (8) | C10—C11 | 1.3825 (9) |
N2—C7 | 1.3455 (8) | C10—H10 | 1.0830 |
N2—C11 | 1.3463 (8) | O10—C24 | 1.3597 (8) |
N2—H2 | 1.0150 | O10—H10A | 0.9800 |
C2—C6 | 1.5068 (9) | C11—H11 | 1.0830 |
C2—C3 | 1.3968 (9) | C13—C18 | 1.4013 (8) |
O3—C12 | 1.2702 (8) | C13—C14 | 1.4019 (8) |
C3—C4 | 1.3914 (9) | C14—C15 | 1.3967 (9) |
C3—H3 | 1.0830 | C15—C16 | 1.3951 (10) |
O4—C12 | 1.2490 (8) | C15—H15 | 1.0830 |
C4—C5 | 1.3849 (10) | C16—C17 | 1.3927 (10) |
C4—H4 | 1.0830 | C16—H16 | 1.0830 |
C5—H5 | 1.0830 | C17—C18 | 1.3907 (9) |
O5—C13 | 1.3611 (8) | C17—H17 | 1.0830 |
O5—H5A | 0.9800 | C19—C20 | 1.3930 (8) |
O6—C14 | 1.3709 (8) | C19—C24 | 1.4016 (8) |
O6—H6 | 0.9800 | C20—C21 | 1.3960 (9) |
C7—C8 | 1.3887 (8) | C21—C22 | 1.3919 (11) |
C7—H7 | 1.0830 | C21—H21 | 1.0830 |
O7—C18 | 1.3739 (8) | C22—C23 | 1.3972 (10) |
O7—H7A | 0.9800 | C22—H22 | 1.0830 |
O8—C19 | 1.3665 (8) | C23—C24 | 1.3917 (9) |
O8—H8 | 0.9800 | C23—H23 | 1.0830 |
| | | |
C1—N1—C5 | 122.26 (5) | N2—C11—C10 | 120.22 (5) |
C1—N1—H1 | 118.78 (5) | N2—C11—H11 | 119.89 (6) |
C5—N1—H1 | 118.96 (6) | C10—C11—H11 | 119.89 (5) |
N1—C1—C2 | 120.13 (5) | O4—C12—O3 | 125.27 (5) |
N1—C1—H1A | 119.95 (5) | O4—C12—C8 | 117.68 (5) |
C2—C1—H1A | 119.93 (5) | O3—C12—C8 | 117.04 (5) |
C7—N2—C11 | 122.18 (5) | O5—C13—C18 | 116.99 (5) |
C7—N2—H2 | 118.99 (5) | O5—C13—C14 | 124.16 (5) |
C11—N2—H2 | 118.83 (6) | C18—C13—C14 | 118.81 (5) |
C6—C2—C1 | 120.81 (5) | O6—C14—C13 | 117.02 (5) |
C6—C2—C3 | 120.66 (5) | O6—C14—C15 | 122.81 (5) |
C1—C2—C3 | 118.52 (5) | C13—C14—C15 | 120.17 (5) |
C2—C3—C4 | 120.18 (5) | C14—C15—C16 | 120.15 (5) |
C2—C3—H3 | 119.79 (6) | C14—C15—H15 | 119.94 (6) |
C4—C3—H3 | 120.04 (5) | C16—C15—H15 | 119.91 (5) |
C5—C4—C3 | 118.63 (5) | C17—C16—C15 | 120.16 (6) |
C5—C4—H4 | 120.67 (5) | C17—C16—H16 | 119.94 (6) |
C3—C4—H4 | 120.70 (5) | C15—C16—H16 | 119.90 (5) |
N1—C5—C4 | 120.28 (5) | C18—C17—C16 | 119.54 (5) |
N1—C5—H5 | 119.85 (6) | C18—C17—H17 | 120.19 (6) |
C4—C5—H5 | 119.87 (5) | C16—C17—H17 | 120.27 (6) |
C13—O5—H5A | 109.52 (5) | O7—C18—C13 | 120.01 (5) |
C14—O6—H6 | 109.45 (5) | O7—C18—C17 | 118.84 (5) |
O2—C6—O1 | 125.28 (6) | C13—C18—C17 | 121.15 (5) |
O2—C6—C2 | 117.21 (5) | O8—C19—C20 | 118.81 (5) |
O1—C6—C2 | 117.48 (5) | O8—C19—C24 | 121.59 (5) |
N2—C7—C8 | 120.10 (5) | C20—C19—C24 | 119.60 (5) |
N2—C7—H7 | 119.79 (5) | O9—C20—C19 | 120.94 (5) |
C8—C7—H7 | 120.11 (5) | O9—C20—C21 | 118.61 (5) |
C18—O7—H7A | 109.50 (5) | C19—C20—C21 | 120.45 (5) |
C19—O8—H8 | 109.55 (5) | C20—C21—C22 | 119.30 (6) |
C12—C8—C7 | 120.08 (5) | C20—C21—H21 | 120.35 (6) |
C12—C8—C9 | 121.28 (5) | C22—C21—H21 | 120.35 (6) |
C7—C8—C9 | 118.64 (5) | C21—C22—C23 | 121.01 (6) |
C8—C9—C10 | 120.02 (5) | C21—C22—H22 | 119.55 (6) |
C8—C9—H9 | 119.95 (6) | C23—C22—H22 | 119.44 (6) |
C10—C9—H9 | 120.02 (5) | C24—C23—C22 | 119.17 (6) |
C20—O9—H9A | 109.52 (5) | C24—C23—H23 | 120.43 (6) |
C11—C10—C9 | 118.81 (5) | C22—C23—H23 | 120.40 (6) |
C11—C10—H10 | 120.67 (5) | O10—C24—C19 | 114.92 (5) |
C9—C10—H10 | 120.52 (5) | O10—C24—C23 | 124.62 (5) |
C24—O10—H10A | 109.39 (5) | C19—C24—C23 | 120.46 (5) |
| | | |
O1—C6—C2—C1 | 1.93 (9) | O7—C18—C13—C14 | −178.74 (8) |
O1—C6—C2—C3 | −176.88 (9) | O7—C18—C17—C16 | 179.30 (8) |
N1—C1—C2—C6 | −177.87 (8) | O7—C18—C17—H17 | −0.65 |
N1—C1—C2—C3 | 0.96 (8) | H7A—O7—C18—C13 | −34.86 |
N1—C5—C4—C3 | 0.33 (8) | H7A—O7—C18—C17 | 146.16 |
N1—C5—C4—H4 | −179.65 | O8—C19—C20—O9 | 0.17 (8) |
H1—N1—C1—C2 | 179.75 | O8—C19—C20—C21 | 179.57 (8) |
H1—N1—C1—H1A | −0.25 | O8—C19—C24—O10 | 0.27 (8) |
H1—N1—C5—C4 | 179.58 | O8—C19—C24—C23 | −179.87 (9) |
H1—N1—C5—H5 | −0.39 | H8—O8—C19—C20 | −158.55 |
C1—N1—C5—C4 | −0.45 (8) | H8—O8—C19—C24 | 21.97 |
C1—N1—C5—H5 | 179.58 | C8—C7—N2—C11 | −1.19 (9) |
C1—C2—C6—O2 | −179.60 (9) | C8—C9—C10—C11 | −1.76 (9) |
C1—C2—C3—C4 | −1.06 (9) | C8—C9—C10—H10 | 178.28 |
C1—C2—C3—H3 | 178.97 | C9—C10—C11—H11 | −179.42 |
H1A—C1—N1—C5 | 179.78 | H9—C9—C8—C12 | 1.70 |
H1A—C1—C2—C6 | 2.14 | H9—C9—C10—C11 | 178.24 |
H1A—C1—C2—C3 | −179.03 | H9—C9—C10—H10 | −1.72 |
O2—C6—C2—C3 | 1.59 (9) | O9—C20—C19—C24 | 179.66 (8) |
N2—C7—C8—C12 | 179.76 (8) | O9—C20—C21—C22 | 179.56 (9) |
N2—C7—C8—C9 | −0.03 (8) | O9—C20—C21—H21 | −0.54 |
N2—C11—C10—C9 | 0.57 (8) | H9A—O9—C20—C19 | −20.60 |
N2—C11—C10—H10 | −179.47 | H9A—O9—C20—C21 | 159.99 |
H2—N2—C7—C8 | 178.97 | C10—C9—C8—C12 | −178.29 (9) |
H2—N2—C7—H7 | −0.93 | H10—C10—C11—H11 | 0.54 |
H2—N2—C11—C10 | −179.24 | O10—C24—C19—C20 | −179.21 (8) |
H2—N2—C11—H11 | 0.75 | O10—C24—C23—C22 | −179.74 (9) |
C2—C1—N1—C5 | −0.22 (8) | O10—C24—C23—H23 | 0.15 |
C2—C3—C4—C5 | 0.43 (9) | H10A—O10—C24—C19 | −160.04 |
C2—C3—C4—H4 | −179.59 | H10A—O10—C24—C23 | 20.11 |
O3—C12—C8—C7 | −0.77 (9) | C13—C18—C17—C16 | 0.33 (8) |
O3—C12—C8—C9 | 179.02 (9) | C13—C18—C17—H17 | −179.62 |
C3—C4—C5—H5 | −179.69 | C13—C14—C15—C16 | 0.92 (8) |
H3—C3—C2—C6 | −2.19 | C13—C14—C15—H15 | −179.10 |
H3—C3—C4—C5 | −179.60 | C14—C13—C18—C17 | 0.22 (8) |
H3—C3—C4—H4 | 0.37 | C14—C15—C16—C17 | −0.36 (9) |
O4—C12—C8—C7 | −179.61 (9) | C14—C15—C16—H16 | 179.59 |
O4—C12—C8—C9 | 0.17 (9) | C15—C14—C13—C18 | −0.84 (8) |
C4—C3—C2—C6 | 177.77 (9) | C15—C16—C17—C18 | −0.26 (9) |
H4—C4—C5—H5 | 0.33 | C15—C16—C17—H17 | 179.69 |
O5—C13—C18—O7 | −0.74 (8) | H15—C15—C16—C17 | 179.65 |
O5—C13—C18—C17 | 178.21 (8) | H15—C15—C16—H16 | −0.39 |
O5—C13—C14—O6 | 1.66 (8) | H16—C16—C17—C18 | 179.79 |
O5—C13—C14—C15 | −178.68 (8) | H16—C16—C17—H17 | −0.27 |
H5A—O5—C13—C18 | 154.23 | C19—C20—C21—C22 | 0.15 (9) |
H5A—O5—C13—C14 | −27.89 | C19—C20—C21—H21 | −179.96 |
O6—C14—C13—C18 | 179.51 (8) | C19—C24—C23—C22 | 0.41 (9) |
O6—C14—C15—C16 | −179.45 (9) | C19—C24—C23—H23 | −179.70 |
O6—C14—C15—H15 | 0.54 | C20—C19—C24—C23 | 0.66 (9) |
H6—O6—C14—C13 | −173.99 | C20—C21—C22—C23 | 0.94 (9) |
H6—O6—C14—C15 | 6.36 | C20—C21—C22—H22 | −178.94 |
C7—N2—C11—C10 | 0.92 (8) | C21—C20—C19—C24 | −0.94 (9) |
C7—N2—C11—H11 | −179.09 | C21—C22—C23—C24 | −1.22 (10) |
C7—C8—C9—C10 | 1.50 (9) | C21—C22—C23—H23 | 178.89 |
C7—C8—C9—H9 | −178.50 | H21—C21—C22—C23 | −178.96 |
H7—C7—N2—C11 | 178.91 | H21—C21—C22—H22 | 1.16 |
H7—C7—C8—C12 | −0.35 | H22—C22—C23—C24 | 178.67 |
H7—C7—C8—C9 | 179.86 | H22—C22—C23—H23 | −1.22 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O1i | 1.01 | 1.71 | 2.7137 (7) | 172 |
N2—H2···O2i | 1.01 | 2.48 | 3.1987 (9) | 127 |
N2—H2···C6i | 1.01 | 2.36 | 3.3145 (9) | 157 |
C5—H5···O8i | 1.08 | 2.56 | 3.1297 (8) | 112 |
C7—H7···O2i | 1.08 | 2.60 | 3.2628 (9) | 119 |
C7—H7···O10i | 1.08 | 2.37 | 3.3124 (8) | 145 |
O6—H6···O9ii | 0.98 | 2.00 | 2.9708 (8) | 169 |
C15—H15···O9ii | 1.08 | 2.59 | 3.3947 (8) | 131 |
N1—H1···O3 | 1.01 | 1.66 | 2.6696 (7) | 175 |
N1—H1···O4 | 1.01 | 2.53 | 3.2085 (9) | 124 |
N1—H1···C12 | 1.01 | 2.36 | 3.2963 (9) | 154 |
C1—H1A···O4 | 1.08 | 2.53 | 3.2175 (8) | 121 |
O5—H5A···O4 | 0.98 | 1.86 | 2.6851 (8) | 140 |
O5—H5A···O6 | 0.98 | 2.42 | 2.7908 (8) | 102 |
O7—H7A···O1 | 0.98 | 1.90 | 2.7045 (7) | 137 |
O8—H8···O10 | 0.98 | 2.26 | 2.6913 (7) | 105 |
C9—H9···O6 | 1.08 | 2.52 | 3.5056 (9) | 151 |
O9—H9A···O8 | 0.98 | 2.32 | 2.7593 (8) | 106 |
O10—H10A···O2 | 0.98 | 1.71 | 2.6349 (8) | 156 |
O8—H8···O3iii | 0.98 | 1.89 | 2.7498 (8) | 144 |
C11—H11···O2iv | 1.08 | 2.48 | 3.1465 (9) | 118 |
C5—H5···O4v | 1.08 | 2.32 | 3.0351 (9) | 122 |
C15—H15···O7vi | 1.08 | 2.62 | 3.4564 (9) | 134 |
C16—H16···O5vi | 1.08 | 2.46 | 3.2500 (8) | 129 |
O9—H9A···O7vii | 0.98 | 1.93 | 2.8143 (7) | 149 |
C21—H21···O10vii | 1.08 | 2.40 | 3.2758 (8) | 136 |
C17—H17···O8viii | 1.08 | 2.60 | 3.4596 (8) | 136 |
Symmetry codes: (i) x, y−1, z; (ii) x, y−1, z+1; (iii) x, y+1, z; (iv) −x+3/2, y−1, z+1/2; (v) −x+3/2, y, z−1/2; (vi) −x+1, −y+1, z+1/2; (vii) −x+1, −y+2, z−1/2; (viii) −x+1, −y+2, z+1/2. |
Crystal data top
C6H5NO2·C6H6O3 | Dx = 1.566 Mg m−3 |
Mr = 249.22 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pca21 | Cell parameters from 2780 reflections |
a = 13.6648 (4) Å | θ = 2.3–52.2° |
b = 11.9321 (3) Å | µ = 0.12 mm−1 |
c = 12.9678 (4) Å | T = 100 K |
V = 2114.40 (10) Å3 | Block, brown |
Z = 8 | 0.35 × 0.29 × 0.24 mm |
F(000) = 1040 | |
Data collection top
Bruker D8 Venture PHOTON II diffractometer | 19169 reflections with > 2.0 σ(I) |
ω and phi scan | Rint = 0.051 |
Absorption correction: analytical SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0673 before and 0.0563 after correction.
The Ratio of minimum to maximum transmission is 0.8999.
The λ/2 correction factor is Not present. | θmax = 52.2°, θmin = 2.3° |
Tmin = 0.675, Tmax = 0.750 | h = −30→21 |
101259 measured reflections | k = −26→24 |
19169 independent reflections | l = −28→28 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.046 | w = 1/[1.223*σ2(Fo2) + 0.0001*Yo2] |
S = 1.01 | (Δ/σ)max = 0.027 |
19169 reflections | Δρmax = 0.34 e Å−3 |
1075 parameters | Δρmin = −0.34 e Å−3 |
0 restraints | Absolute structure: Rogers (1981), 8469 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Rogers parameter: 1 |
Special details top
Refinement. Refinement of F2 against reflections.
The threshold expression of F2 > 2sigma(F2) is
used for calculating R-factors(gt) and is not
relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice
as large as those based on F, and R-factors based on
ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.68090 (2) | 0.64338 (3) | 0.547620 (6) | 0.015210 (14) | |
N1 | 0.68875 (2) | 0.35065 (3) | 0.37576 (4) | 0.011509 (13) | |
H1 | 0.68420 | 0.27141 | 0.41620 | 0.02558 | |
C1 | 0.68309 (3) | 0.44392 (3) | 0.43328 (4) | 0.010812 (14) | |
H1A | 0.66960 | 0.42702 | 0.51436 | 0.02649 | |
O2 | 0.68742 (2) | 0.74541 (3) | 0.40319 (4) | 0.017211 (15) | |
N2 | 0.67965 (2) | −0.14701 (3) | 0.62887 (3) | 0.011375 (13) | |
H2 | 0.67924 | −0.22524 | 0.58805 | 0.02593 | |
C2 | 0.68698 (2) | 0.54858 (3) | 0.38670 (4) | 0.010287 (14) | |
O3 | 0.68263 (2) | 0.14660 (3) | 0.46002 (3) | 0.015081 (14) | |
C3 | 0.69544 (3) | 0.55390 (3) | 0.27960 (4) | 0.012285 (15) | |
H3 | 0.70080 | 0.63357 | 0.23922 | 0.02621 | |
O4 | 0.67786 (2) | 0.24881 (3) | 0.60438 (4) | 0.015723 (13) | |
C4 | 0.70135 (3) | 0.45585 (3) | 0.22178 (4) | 0.013279 (16) | |
H4 | 0.71476 | 0.45861 | 0.13934 | 0.02551 | |
C5 | 0.69796 (3) | 0.35401 (3) | 0.27262 (4) | 0.012910 (16) | |
H5 | 0.70442 | 0.27493 | 0.23204 | 0.02345 | |
O5 | 0.56144 (2) | 0.40676 (2) | 0.68628 (3) | 0.014828 (13) | |
H5A | 0.59914 | 0.33578 | 0.68516 | 0.02559 | |
O6 | 0.58028 (2) | 0.28220 (2) | 0.86722 (4) | 0.016431 (13) | |
H6 | 0.57488 | 0.24894 | 0.93655 | 0.02326 | |
C6 | 0.68411 (3) | 0.65407 (3) | 0.45043 (4) | 0.011740 (15) | |
C7 | 0.68004 (3) | −0.05256 (3) | 0.57242 (4) | 0.011191 (15) | |
H7 | 0.68071 | −0.06829 | 0.49002 | 0.02381 | |
O7 | 0.54119 (2) | 0.63227 (2) | 0.69511 (3) | 0.013985 (12) | |
H7A | 0.58036 | 0.59732 | 0.63949 | 0.02620 | |
O8 | 0.57053 (2) | 1.13634 (2) | 0.28401 (3) | 0.014451 (12) | |
H8 | 0.60116 | 1.10197 | 0.34559 | 0.02487 | |
C8 | 0.67818 (2) | 0.05129 (3) | 0.62078 (4) | 0.010193 (14) | |
C9 | 0.67578 (3) | 0.05494 (3) | 0.72828 (4) | 0.012078 (15) | |
H9 | 0.67177 | 0.13523 | 0.76801 | 0.02486 | |
O9 | 0.54931 (2) | 1.19663 (2) | 0.07989 (4) | 0.015353 (13) | |
H9A | 0.52751 | 1.24376 | 0.13812 | 0.02641 | |
C10 | 0.67774 (3) | −0.04438 (3) | 0.78495 (4) | 0.012692 (15) | |
H10 | 0.67737 | −0.04356 | 0.86869 | 0.02400 | |
O10 | 0.58562 (2) | 0.91928 (2) | 0.33847 (3) | 0.014056 (13) | |
H10A | 0.61384 | 0.84387 | 0.35324 | 0.02639 | |
C11 | 0.67919 (3) | −0.14549 (3) | 0.73257 (4) | 0.012351 (15) | |
H11 | 0.68115 | −0.22669 | 0.77022 | 0.02658 | |
C12 | 0.67898 (3) | 0.15756 (3) | 0.55730 (4) | 0.011442 (15) | |
C13 | 0.56219 (2) | 0.45555 (3) | 0.78113 (4) | 0.010470 (13) | |
C14 | 0.57028 (2) | 0.39612 (3) | 0.87400 (4) | 0.011408 (14) | |
C15 | 0.56856 (3) | 0.45315 (3) | 0.96799 (4) | 0.013364 (16) | |
H15 | 0.57734 | 0.40278 | 1.03727 | 0.02636 | |
C16 | 0.55731 (3) | 0.56930 (3) | 0.97008 (4) | 0.014164 (16) | |
H16 | 0.55366 | 0.61271 | 1.04369 | 0.02659 | |
C17 | 0.54835 (3) | 0.62915 (3) | 0.87837 (4) | 0.012971 (15) | |
H17 | 0.53055 | 0.71786 | 0.87439 | 0.02712 | |
C18 | 0.55113 (2) | 0.57221 (3) | 0.78479 (4) | 0.010619 (13) | |
C19 | 0.56858 (2) | 1.05468 (3) | 0.21025 (4) | 0.010177 (14) | |
C20 | 0.55765 (2) | 1.08586 (3) | 0.10726 (4) | 0.011211 (14) | |
C21 | 0.55605 (3) | 1.00476 (3) | 0.02999 (4) | 0.014420 (17) | |
H21 | 0.54060 | 1.03286 | −0.04810 | 0.02647 | |
C22 | 0.56525 (3) | 0.89216 (4) | 0.05637 (4) | 0.016084 (17) | |
H22 | 0.56100 | 0.82864 | −0.00360 | 0.02600 | |
C23 | 0.57464 (3) | 0.85922 (3) | 0.15933 (4) | 0.013821 (16) | |
H23 | 0.58265 | 0.77247 | 0.18401 | 0.02656 | |
C24 | 0.57651 (3) | 0.94088 (3) | 0.23599 (4) | 0.010626 (14) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.02419 (13) | 0.01087 (11) | 0.01058 (11) | −0.00067 (9) | 0.00410 (9) | −0.00163 (8) |
N1 | 0.01425 (10) | 0.00881 (11) | 0.01146 (11) | −0.00052 (8) | 0.00022 (9) | −0.00081 (9) |
H1 | 0.03895 | 0.01701 | 0.02077 | 0.00008 | 0.00127 | 0.00250 |
C1 | 0.01457 (12) | 0.00884 (12) | 0.00903 (11) | 0.00000 (9) | 0.00024 (9) | 0.00014 (9) |
H1A | 0.03980 | 0.02492 | 0.01473 | 0.00040 | 0.00213 | 0.00041 |
O2 | 0.02650 (13) | 0.00853 (10) | 0.01661 (13) | 0.00223 (9) | 0.00198 (10) | 0.00208 (9) |
N2 | 0.01487 (11) | 0.00893 (11) | 0.01032 (11) | 0.00079 (9) | 0.00019 (9) | 0.00004 (9) |
H2 | 0.03877 | 0.01714 | 0.02187 | −0.00073 | −0.00055 | −0.00296 |
C2 | 0.01306 (11) | 0.00854 (11) | 0.00926 (12) | 0.00066 (9) | 0.00060 (9) | 0.00024 (9) |
O3 | 0.02558 (13) | 0.01055 (11) | 0.00911 (10) | −0.00177 (9) | −0.00177 (9) | 0.00041 (8) |
C3 | 0.01592 (12) | 0.01146 (13) | 0.00948 (12) | −0.00022 (9) | 0.00051 (10) | 0.00114 (11) |
H3 | 0.03908 | 0.01726 | 0.02229 | 0.00049 | 0.00065 | 0.00380 |
O4 | 0.02531 (13) | 0.00856 (10) | 0.01329 (11) | −0.00050 (9) | 0.00021 (10) | −0.00215 (9) |
C4 | 0.01663 (13) | 0.01420 (14) | 0.00900 (12) | −0.00131 (10) | 0.00125 (10) | −0.00125 (10) |
H4 | 0.03677 | 0.02522 | 0.01455 | 0.00046 | 0.00126 | 0.00000 |
C5 | 0.01509 (12) | 0.01172 (13) | 0.01192 (14) | −0.00118 (10) | 0.00166 (10) | −0.00292 (10) |
H5 | 0.03025 | 0.01899 | 0.02110 | 0.00494 | −0.00072 | −0.00064 |
O5 | 0.02301 (12) | 0.01218 (10) | 0.00930 (10) | 0.00285 (9) | −0.00268 (9) | −0.00170 (8) |
H5A | 0.03699 | 0.01790 | 0.02187 | 0.00093 | 0.00087 | −0.00484 |
O6 | 0.02442 (12) | 0.01080 (10) | 0.01407 (11) | −0.00029 (9) | −0.00089 (10) | 0.00227 (9) |
H6 | 0.03171 | 0.02153 | 0.01654 | 0.00030 | 0.00123 | 0.00207 |
C6 | 0.01570 (12) | 0.00855 (12) | 0.01097 (12) | 0.00095 (10) | 0.00196 (10) | 0.00022 (10) |
C7 | 0.01545 (13) | 0.00932 (12) | 0.00880 (11) | 0.00008 (10) | −0.00036 (10) | −0.00090 (9) |
H7 | 0.03050 | 0.02259 | 0.01834 | 0.00474 | 0.00370 | −0.00120 |
O7 | 0.02046 (11) | 0.01166 (10) | 0.00984 (10) | 0.00334 (9) | 0.00276 (9) | 0.00183 (8) |
H7A | 0.03827 | 0.02492 | 0.01542 | −0.00022 | 0.00007 | −0.00079 |
O8 | 0.02360 (11) | 0.00921 (9) | 0.01054 (9) | 0.00039 (8) | −0.00356 (10) | −0.00151 (8) |
H8 | 0.03440 | 0.02145 | 0.01874 | 0.00412 | −0.00433 | 0.00058 |
C8 | 0.01337 (12) | 0.00879 (12) | 0.00842 (11) | −0.00035 (9) | −0.00048 (9) | −0.00025 (9) |
C9 | 0.01624 (13) | 0.01110 (12) | 0.00889 (12) | −0.00016 (10) | 0.00012 (10) | −0.00092 (10) |
H9 | 0.03523 | 0.02041 | 0.01895 | 0.00352 | 0.00206 | −0.00199 |
O9 | 0.02226 (12) | 0.01255 (11) | 0.01125 (10) | 0.00244 (9) | 0.00034 (9) | 0.00280 (8) |
H9A | 0.03903 | 0.01756 | 0.02263 | 0.00032 | 0.00076 | −0.00407 |
C10 | 0.01621 (13) | 0.01338 (13) | 0.00849 (11) | 0.00053 (10) | 0.00059 (11) | 0.00066 (11) |
H10 | 0.03339 | 0.01774 | 0.02085 | 0.00506 | −0.00027 | 0.00034 |
O10 | 0.02160 (11) | 0.01085 (10) | 0.00972 (10) | 0.00193 (9) | 0.00043 (9) | 0.00120 (8) |
H10A | 0.03845 | 0.02538 | 0.01535 | −0.00071 | 0.00009 | 0.00011 |
C11 | 0.01498 (12) | 0.01117 (13) | 0.01090 (13) | 0.00111 (10) | 0.00040 (10) | 0.00185 (10) |
H11 | 0.03862 | 0.01788 | 0.02324 | −0.00089 | −0.00043 | 0.00466 |
C12 | 0.01627 (12) | 0.00863 (12) | 0.00943 (12) | −0.00071 (10) | −0.00124 (10) | −0.00051 (9) |
C13 | 0.01329 (11) | 0.00987 (11) | 0.00825 (10) | 0.00019 (9) | −0.00089 (9) | 0.00007 (10) |
C14 | 0.01361 (11) | 0.01111 (12) | 0.00950 (11) | −0.00042 (9) | −0.00055 (10) | 0.00130 (10) |
C15 | 0.01608 (13) | 0.01538 (14) | 0.00863 (11) | −0.00056 (11) | −0.00007 (10) | 0.00106 (10) |
H15 | 0.03769 | 0.02408 | 0.01731 | 0.00164 | −0.00069 | 0.00415 |
C16 | 0.01809 (13) | 0.01565 (14) | 0.00876 (11) | −0.00005 (11) | 0.00133 (11) | −0.00138 (10) |
H16 | 0.03836 | 0.02448 | 0.01693 | 0.00192 | 0.00020 | −0.00470 |
C17 | 0.01675 (13) | 0.01198 (13) | 0.01018 (12) | 0.00059 (10) | 0.00215 (11) | −0.00129 (10) |
H17 | 0.04021 | 0.01660 | 0.02457 | 0.00338 | −0.00003 | −0.00083 |
C18 | 0.01325 (11) | 0.00990 (11) | 0.00871 (10) | 0.00060 (9) | 0.00111 (10) | 0.00007 (10) |
C19 | 0.01269 (11) | 0.00938 (12) | 0.00846 (11) | 0.00008 (9) | −0.00089 (9) | −0.00032 (9) |
C20 | 0.01304 (11) | 0.01185 (13) | 0.00874 (11) | 0.00127 (10) | −0.00071 (9) | 0.00047 (10) |
C21 | 0.01743 (14) | 0.01667 (15) | 0.00916 (11) | 0.00397 (11) | −0.00129 (10) | −0.00194 (10) |
H21 | 0.03813 | 0.02520 | 0.01608 | 0.00221 | −0.00174 | 0.00266 |
C22 | 0.02131 (15) | 0.01483 (14) | 0.01211 (13) | 0.00414 (12) | −0.00250 (12) | −0.00449 (11) |
H22 | 0.03732 | 0.02102 | 0.01965 | 0.00179 | −0.00033 | −0.00504 |
C23 | 0.01756 (13) | 0.01077 (13) | 0.01313 (13) | 0.00189 (10) | −0.00117 (11) | −0.00288 (10) |
H23 | 0.03935 | 0.01617 | 0.02415 | 0.00233 | −0.00057 | 0.00205 |
C24 | 0.01310 (11) | 0.00947 (12) | 0.00930 (11) | 0.00031 (9) | −0.00010 (9) | −0.00044 (9) |
Geometric parameters (Å, º) top
O1—C6 | 1.2675 (5) | C8—C12 | 1.5117 (5) |
N1—C1 | 1.3420 (5) | C8—C9 | 1.3952 (5) |
N1—C5 | 1.3440 (5) | C9—C10 | 1.3947 (5) |
N1—H1 | 1.0829 | C9—H9 | 1.0892 |
C1—C2 | 1.3883 (5) | O9—C20 | 1.3733 (5) |
C1—H1A | 1.0863 | O9—H9A | 0.9874 |
O2—C6 | 1.2511 (5) | C10—C11 | 1.3846 (5) |
N2—C7 | 1.3439 (5) | C10—H10 | 1.0860 |
N2—C11 | 1.3449 (5) | O10—C24 | 1.3595 (5) |
N2—H2 | 1.0731 | O10—H10A | 0.9975 |
C2—C6 | 1.5063 (5) | C11—H11 | 1.0853 |
C2—C3 | 1.3951 (5) | C13—C18 | 1.4009 (5) |
O3—C12 | 1.2693 (5) | C13—C14 | 1.4020 (5) |
C3—C4 | 1.3920 (5) | C14—C15 | 1.3961 (5) |
C3—H3 | 1.0877 | C15—C16 | 1.3947 (6) |
O4—C12 | 1.2484 (5) | C15—H15 | 1.0875 |
C4—C5 | 1.3832 (6) | C16—C17 | 1.3926 (6) |
C4—H4 | 1.0852 | C16—H16 | 1.0872 |
C5—H5 | 1.0840 | C17—C18 | 1.3913 (5) |
O5—C13 | 1.3609 (5) | C17—H17 | 1.0873 |
O5—H5A | 0.9914 | C19—C20 | 1.3945 (5) |
O6—C14 | 1.3690 (5) | C19—C24 | 1.4025 (5) |
O6—H6 | 0.9855 | C20—C21 | 1.3931 (5) |
C7—C8 | 1.3890 (5) | C21—C22 | 1.3921 (6) |
C7—H7 | 1.0850 | C21—H21 | 1.0874 |
O7—C18 | 1.3728 (5) | C22—C23 | 1.3976 (6) |
O7—H7A | 0.9903 | C22—H22 | 1.0876 |
O8—C19 | 1.3657 (4) | C23—C24 | 1.3921 (5) |
O8—H8 | 0.9905 | C23—H23 | 1.0890 |
| | | |
C1—N1—C5 | 122.26 (3) | N2—C11—C10 | 120.16 (3) |
C1—N1—H1 | 116.84 | N2—C11—H11 | 115.95 |
C5—N1—H1 | 120.89 | C10—C11—H11 | 123.88 |
N1—C1—C2 | 120.13 (3) | O4—C12—O3 | 125.19 (3) |
N1—C1—H1A | 113.20 | O4—C12—C8 | 117.73 (3) |
C2—C1—H1A | 126.48 | O3—C12—C8 | 117.07 (3) |
C7—N2—C11 | 122.23 (3) | O5—C13—C18 | 117.06 (3) |
C7—N2—H2 | 117.43 | O5—C13—C14 | 124.10 (3) |
C11—N2—H2 | 120.33 | C18—C13—C14 | 118.81 (3) |
C6—C2—C1 | 120.80 (3) | O6—C14—C13 | 117.06 (3) |
C6—C2—C3 | 120.68 (3) | O6—C14—C15 | 122.80 (3) |
C1—C2—C3 | 118.51 (3) | C13—C14—C15 | 120.14 (3) |
C2—C3—C4 | 120.18 (3) | C14—C15—C16 | 120.21 (3) |
C2—C3—H3 | 121.64 | C14—C15—H15 | 116.74 |
C4—C3—H3 | 118.12 | C16—C15—H15 | 123.05 |
C5—C4—C3 | 118.67 (3) | C17—C16—C15 | 120.18 (3) |
C5—C4—H4 | 120.12 | C17—C16—H16 | 120.09 |
C3—C4—H4 | 120.99 | C15—C16—H16 | 119.71 |
N1—C5—C4 | 120.24 (3) | C18—C17—C16 | 119.47 (3) |
N1—C5—H5 | 117.69 | C18—C17—H17 | 116.11 |
C4—C5—H5 | 122.05 | C16—C17—H17 | 124.02 |
C13—O5—H5A | 112.01 | O7—C18—C13 | 120.04 (3) |
C14—O6—H6 | 109.50 | O7—C18—C17 | 118.77 (3) |
O2—C6—O1 | 125.16 (3) | C13—C18—C17 | 121.18 (3) |
O2—C6—C2 | 117.28 (3) | O8—C19—C20 | 118.85 (3) |
O1—C6—C2 | 117.54 (3) | O8—C19—C24 | 121.51 (3) |
N2—C7—C8 | 120.14 (3) | C20—C19—C24 | 119.64 (3) |
N2—C7—H7 | 113.04 | O9—C20—C19 | 120.87 (3) |
C8—C7—H7 | 126.81 | O9—C20—C21 | 118.78 (3) |
C18—O7—H7A | 110.11 | C19—C20—C21 | 120.35 (3) |
C19—O8—H8 | 106.11 | C20—C21—C22 | 119.48 (3) |
C12—C8—C7 | 120.15 (3) | C20—C21—H21 | 117.30 |
C12—C8—C9 | 121.20 (3) | C22—C21—H21 | 122.96 |
C7—C8—C9 | 118.64 (3) | C21—C22—C23 | 120.96 (3) |
C8—C9—C10 | 119.97 (3) | C21—C22—H22 | 119.47 |
C8—C9—H9 | 120.08 | C23—C22—H22 | 119.48 |
C10—C9—H9 | 119.94 | C24—C23—C22 | 119.14 (3) |
C20—O9—H9A | 112.05 | C24—C23—H23 | 116.97 |
C11—C10—C9 | 118.82 (3) | C22—C23—H23 | 123.87 |
C11—C10—H10 | 119.90 | O10—C24—C19 | 115.04 (3) |
C9—C10—H10 | 121.27 | O10—C24—C23 | 124.55 (3) |
C24—O10—H10A | 113.21 | C19—C24—C23 | 120.41 (3) |
| | | |
O1—C6—C2—C1 | 1.99 (5) | O7—C18—C13—C14 | −178.78 (4) |
O1—C6—C2—C3 | −176.82 (5) | O7—C18—C17—C16 | 179.34 (4) |
N1—C1—C2—C6 | −177.94 (5) | O7—C18—C17—H17 | 6.29 |
N1—C1—C2—C3 | 0.88 (5) | H7A—O7—C18—C13 | −34.06 |
N1—C5—C4—C3 | 0.25 (5) | H7A—O7—C18—C17 | 146.99 |
N1—C5—C4—H4 | 174.97 | O8—C19—C20—O9 | 0.24 (5) |
H1—N1—C1—C2 | −179.09 | O8—C19—C20—C21 | 179.55 (5) |
H1—N1—C1—H1A | −3.84 | O8—C19—C24—O10 | 0.30 (4) |
H1—N1—C5—C4 | 178.46 | O8—C19—C24—C23 | −179.79 (5) |
H1—N1—C5—H5 | −3.10 | H8—O8—C19—C20 | −160.67 |
C1—N1—C5—C4 | −0.38 (5) | H8—O8—C19—C24 | 19.86 |
C1—N1—C5—H5 | 178.06 | C8—C7—N2—C11 | −1.17 (5) |
C1—C2—C6—O2 | −179.65 (5) | C8—C9—C10—C11 | −1.87 (5) |
C1—C2—C3—C4 | −1.00 (5) | C8—C9—C10—H10 | 178.79 |
C1—C2—C3—H3 | −178.31 | C9—C10—C11—H11 | 179.65 |
H1A—C1—N1—C5 | 175.05 | H9—C9—C8—C12 | 2.22 |
H1A—C1—C2—C6 | 7.49 | H9—C9—C10—C11 | 177.63 |
H1A—C1—C2—C3 | −173.68 | H9—C9—C10—H10 | −1.71 |
O2—C6—C2—C3 | 1.55 (5) | O9—C20—C19—C24 | 179.73 (5) |
N2—C7—C8—C12 | 179.79 (5) | O9—C20—C21—C22 | 179.46 (5) |
N2—C7—C8—C9 | −0.09 (5) | O9—C20—C21—H21 | −6.22 |
N2—C11—C10—C9 | 0.65 (5) | H9A—O9—C20—C19 | −21.35 |
N2—C11—C10—H10 | 180.00 | H9A—O9—C20—C21 | 159.33 |
H2—N2—C7—C8 | 178.44 | C10—C9—C8—C12 | −178.28 (5) |
H2—N2—C7—H7 | −0.64 | H10—C10—C11—H11 | −1.00 |
H2—N2—C11—C10 | −178.71 | O10—C24—C19—C20 | −179.17 (4) |
H2—N2—C11—H11 | 2.21 | O10—C24—C23—C22 | −179.79 (5) |
C2—C1—N1—C5 | −0.20 (5) | O10—C24—C23—H23 | −1.35 |
C2—C3—C4—C5 | 0.45 (5) | H10A—O10—C24—C19 | −159.93 |
C2—C3—C4—H4 | −174.22 | H10A—O10—C24—C23 | 20.17 |
O3—C12—C8—C7 | −0.87 (5) | C13—C18—C17—C16 | 0.40 (5) |
O3—C12—C8—C9 | 179.00 (5) | C13—C18—C17—H17 | −172.65 |
C3—C4—C5—H5 | −178.12 | C13—C14—C15—C16 | 0.96 (5) |
H3—C3—C2—C6 | 0.52 | C13—C14—C15—H15 | −178.22 |
H3—C3—C4—C5 | 177.84 | C14—C13—C18—C17 | 0.15 (5) |
H3—C3—C4—H4 | 3.18 | C14—C15—C16—C17 | −0.41 (5) |
O4—C12—C8—C7 | −179.55 (5) | C14—C15—C16—H16 | 178.01 |
O4—C12—C8—C9 | 0.32 (5) | C15—C14—C13—C18 | −0.83 (5) |
C4—C3—C2—C6 | 177.83 (5) | C15—C16—C17—C18 | −0.27 (5) |
H4—C4—C5—H5 | −3.40 | C15—C16—C17—H17 | 172.20 |
O5—C13—C18—O7 | −0.67 (4) | H15—C15—C16—C17 | 178.72 |
O5—C13—C18—C17 | 178.26 (5) | H15—C15—C16—H16 | −2.86 |
O5—C13—C14—O6 | 1.57 (4) | H16—C16—C17—C18 | −178.68 |
O5—C13—C14—C15 | −178.80 (5) | H16—C16—C17—H17 | −6.21 |
H5A—O5—C13—C18 | 152.88 | C19—C20—C21—C22 | 0.14 (5) |
H5A—O5—C13—C14 | −29.12 | C19—C20—C21—H21 | 174.46 |
O6—C14—C13—C18 | 179.54 (5) | C19—C24—C23—C22 | 0.31 (5) |
O6—C14—C15—C16 | −179.43 (5) | C19—C24—C23—H23 | 178.75 |
O6—C14—C15—H15 | 1.39 | C20—C19—C24—C23 | 0.74 (5) |
H6—O6—C14—C13 | −171.20 | C20—C21—C22—C23 | 0.94 (5) |
H6—O6—C14—C15 | 9.18 | C20—C21—C22—H22 | 177.49 |
C7—N2—C11—C10 | 0.88 (5) | C21—C20—C19—C24 | −0.96 (5) |
C7—N2—C11—H11 | −178.19 | C21—C22—C23—C24 | −1.16 (6) |
C7—C8—C9—C10 | 1.59 (5) | C21—C22—C23—H23 | −179.48 |
C7—C8—C9—H9 | −177.90 | H21—C21—C22—C23 | −173.05 |
H7—C7—N2—C11 | 179.75 | H21—C21—C22—H22 | 3.51 |
H7—C7—C8—C12 | −1.27 | H22—C22—C23—C24 | −177.71 |
H7—C7—C8—C9 | 178.85 | H22—C22—C23—H23 | 3.97 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O1i | 1.07 | 1.65 | 2.7140 (4) | 169 (1) |
N2—H2···O2i | 1.07 | 2.42 | 3.1975 (5) | 128 (1) |
N2—H2···C6i | 1.07 | 2.29 | 3.3153 (5) | 158 (1) |
C5—H5···O8i | 1.08 | 2.56 | 3.1304 (5) | 112 |
C7—H7···O2i | 1.09 | 2.49 | 3.2615 (5) | 126 |
C7—H7···O10i | 1.09 | 2.36 | 3.3138 (5) | 145 |
O6—H6···O9ii | 0.99 | 1.99 | 2.9711 (5) | 172 (1) |
C15—H15···O9ii | 1.09 | 2.55 | 3.3975 (5) | 134 |
N1—H1···O3 | 1.08 | 1.59 | 2.6700 (4) | 172 (1) |
N1—H1···O4 | 1.08 | 2.46 | 3.2075 (5) | 125 (1) |
N1—H1···C12 | 1.08 | 2.28 | 3.2968 (5) | 156 (1) |
C1—H1A···O4 | 1.09 | 2.43 | 3.2168 (5) | 128 |
O5—H5A···O4 | 0.99 | 1.83 | 2.6853 (4) | 143 (1) |
O7—H7A···O1 | 0.99 | 1.90 | 2.7056 (4) | 137 (1) |
O8—H8···O10 | 0.99 | 2.19 | 2.6925 (4) | 110 (1) |
C9—H9···O6 | 1.09 | 2.51 | 3.5076 (5) | 151 |
O9—H9A···O8 | 0.99 | 2.36 | 2.7582 (4) | 103 (1) |
O10—H10A···O2 | 1.00 | 1.68 | 2.6350 (4) | 160 (1) |
O8—H8···O3iii | 0.99 | 1.93 | 2.7515 (4) | 138 |
C11—H11···O2iv | 1.09 | 2.51 | 3.1485 (5) | 116 |
C5—H5···O4v | 1.08 | 2.33 | 3.0356 (5) | 121 |
C16—H16···O5vi | 1.09 | 2.44 | 3.2519 (5) | 130 |
O9—H9A···O7vii | 0.99 | 1.90 | 2.8160 (4) | 153 (1) |
C21—H21···O10vii | 1.09 | 2.34 | 3.2767 (5) | 143 |
C17—H17···O8viii | 1.09 | 2.51 | 3.4592 (5) | 145 |
Symmetry codes: (i) x, y−1, z; (ii) x, y−1, z+1; (iii) x, y+1, z; (iv) −x+3/2, y−1, z+1/2; (v) −x+3/2, y, z−1/2; (vi) −x+1, −y+1, z+1/2; (vii) −x+1, −y+2, z−1/2; (viii) −x+1, −y+2, z+1/2. |
Crystal data top
C6H5NO2·C6H6O3 | Dx = 1.566 Mg m−3 |
Mr = 249.22 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pca21 | Cell parameters from 2780 reflections |
a = 13.6648 (4) Å | θ = 2.3–52.2° |
b = 11.9321 (3) Å | µ = 0.12 mm−1 |
c = 12.9678 (4) Å | T = 100 K |
V = 2114.40 (10) Å3 | Block, brown |
Z = 8 | 0.35 × 0.29 × 0.24 mm |
F(000) = 1040 | |
Data collection top
Bruker D8 Venture PHOTON II diffractometer | 18901 reflections with > 2.0 σ(I) |
ω and phi scan | Rint = 0.051 |
Absorption correction: analytical SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0673 before and 0.0563 after correction.
The Ratio of minimum to maximum transmission is 0.8999.
The λ/2 correction factor is Not present. | θmax = 52.2°, θmin = 2.3° |
Tmin = 0.675, Tmax = 0.750 | h = −30→21 |
101259 measured reflections | k = −26→24 |
23980 independent reflections | l = −28→28 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.041 | w = 1/[σ2(Fo2) + (0.0565P)2 + 0.052P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.108 | (Δ/σ)max = 0.001 |
S = 1.04 | Δρmax = 0.60 e Å−3 |
23980 reflections | Δρmin = −0.29 e Å−3 |
337 parameters | Absolute structure: Flack x determined using 7550 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
1 restraint | Absolute structure parameter: 0.33 (13) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.68082 (5) | 0.64347 (5) | 0.54764 (5) | 0.01535 (10) | |
N1 | 0.68877 (5) | 0.35064 (5) | 0.37566 (6) | 0.01162 (8) | |
H1 | 0.686355 | 0.285033 | 0.406564 | 0.014* | |
C1 | 0.68307 (5) | 0.44402 (6) | 0.43316 (6) | 0.01072 (9) | |
H1A | 0.676324 | 0.438433 | 0.505889 | 0.013* | |
O2 | 0.68742 (5) | 0.74545 (5) | 0.40301 (6) | 0.01741 (11) | |
N2 | 0.67966 (5) | −0.14702 (5) | 0.62883 (5) | 0.01139 (8) | |
H2 | 0.679790 | −0.212087 | 0.596891 | 0.014* | |
C2 | 0.68700 (5) | 0.54851 (5) | 0.38668 (5) | 0.01018 (9) | |
O3 | 0.68259 (5) | 0.14651 (5) | 0.45988 (5) | 0.01530 (9) | |
C3 | 0.69544 (5) | 0.55387 (6) | 0.27962 (6) | 0.01225 (9) | |
H3 | 0.697158 | 0.624623 | 0.246069 | 0.015* | |
O4 | 0.67779 (5) | 0.24879 (5) | 0.60445 (5) | 0.01592 (9) | |
C4 | 0.70134 (6) | 0.45578 (6) | 0.22175 (6) | 0.01330 (10) | |
H4 | 0.707518 | 0.458712 | 0.148835 | 0.016* | |
C5 | 0.69803 (5) | 0.35398 (6) | 0.27269 (6) | 0.01294 (10) | |
H5A | 0.702336 | 0.286143 | 0.234608 | 0.016* | |
O5 | 0.56137 (5) | 0.40691 (5) | 0.68616 (5) | 0.01506 (9) | |
H5 | 0.5908 (13) | 0.3478 (16) | 0.6884 (3) | 0.023* | |
O6 | 0.58033 (5) | 0.28210 (5) | 0.86705 (5) | 0.01673 (10) | |
H6 | 0.5771 (13) | 0.2562 (8) | 0.9213 (16) | 0.025* | |
C6 | 0.68414 (5) | 0.65411 (6) | 0.45048 (6) | 0.01154 (9) | |
C7 | 0.67999 (5) | −0.05258 (6) | 0.57240 (6) | 0.01108 (9) | |
H7A | 0.681475 | −0.056849 | 0.499266 | 0.013* | |
O7 | 0.54108 (5) | 0.63227 (5) | 0.69503 (5) | 0.01410 (9) | |
H7 | 0.5731 (12) | 0.6035 (12) | 0.6504 (12) | 0.021* | |
O8 | 0.57046 (5) | 1.13643 (5) | 0.28395 (5) | 0.01470 (9) | |
H8 | 0.5982 (12) | 1.1132 (8) | 0.3349 (14) | 0.022* | |
C8 | 0.67815 (5) | 0.05133 (6) | 0.62076 (5) | 0.01010 (9) | |
C9 | 0.67580 (5) | 0.05490 (6) | 0.72827 (6) | 0.01197 (9) | |
H9A | 0.672934 | 0.124988 | 0.762886 | 0.014* | |
O9 | 0.54934 (5) | 1.19671 (5) | 0.07977 (5) | 0.01553 (9) | |
H9 | 0.5312 (13) | 1.2341 (10) | 0.1306 (13) | 0.023* | |
C10 | 0.67766 (5) | −0.04442 (6) | 0.78492 (6) | 0.01265 (10) | |
H10A | 0.677895 | −0.042770 | 0.858163 | 0.015* | |
O10 | 0.58561 (5) | 0.91940 (5) | 0.33843 (5) | 0.01431 (9) | |
H10 | 0.6080 (13) | 0.8565 (15) | 0.34655 (19) | 0.021* | |
C11 | 0.67915 (5) | −0.14535 (6) | 0.73254 (6) | 0.01221 (10) | |
H11 | 0.679823 | −0.213800 | 0.769956 | 0.015* | |
C12 | 0.67897 (5) | 0.15765 (6) | 0.55722 (6) | 0.01125 (9) | |
C13 | 0.56221 (5) | 0.45548 (5) | 0.78113 (6) | 0.01051 (8) | |
C14 | 0.57028 (5) | 0.39613 (6) | 0.87398 (6) | 0.01125 (9) | |
C15 | 0.56847 (6) | 0.45310 (7) | 0.96798 (6) | 0.01328 (10) | |
H15 | 0.574919 | 0.412630 | 1.030703 | 0.016* | |
C16 | 0.55723 (6) | 0.56921 (7) | 0.97011 (6) | 0.01410 (10) | |
H16 | 0.555671 | 0.607600 | 1.034274 | 0.017* | |
C17 | 0.54828 (6) | 0.62910 (6) | 0.87831 (6) | 0.01287 (9) | |
H17 | 0.540313 | 0.708177 | 0.879637 | 0.015* | |
C18 | 0.55110 (5) | 0.57222 (6) | 0.78476 (6) | 0.01052 (8) | |
C19 | 0.56865 (5) | 1.05461 (6) | 0.21035 (5) | 0.01024 (9) | |
C20 | 0.55768 (5) | 1.08585 (6) | 0.10737 (6) | 0.01107 (9) | |
C21 | 0.55606 (6) | 1.00465 (7) | 0.02986 (6) | 0.01446 (11) | |
H21 | 0.548736 | 1.026000 | −0.040289 | 0.017* | |
C22 | 0.56529 (6) | 0.89208 (7) | 0.05642 (7) | 0.01591 (11) | |
H22 | 0.565218 | 0.836771 | 0.003723 | 0.019* | |
C23 | 0.57464 (6) | 0.85923 (6) | 0.15926 (6) | 0.01364 (10) | |
H23 | 0.579661 | 0.782124 | 0.176734 | 0.016* | |
C24 | 0.57650 (5) | 0.94088 (6) | 0.23589 (5) | 0.01050 (9) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0241 (3) | 0.01132 (19) | 0.0106 (2) | −0.00069 (17) | 0.00425 (17) | −0.00178 (15) |
N1 | 0.0142 (2) | 0.00903 (18) | 0.0116 (2) | −0.00026 (15) | 0.00022 (16) | −0.00081 (16) |
C1 | 0.0141 (2) | 0.0088 (2) | 0.0093 (2) | 0.00005 (17) | 0.00028 (17) | 0.00001 (16) |
O2 | 0.0268 (3) | 0.00857 (18) | 0.0169 (2) | 0.00219 (18) | 0.0020 (2) | 0.00232 (17) |
N2 | 0.0147 (2) | 0.00907 (19) | 0.0104 (2) | 0.00089 (15) | 0.00014 (16) | 0.00003 (15) |
C2 | 0.0127 (2) | 0.0088 (2) | 0.0090 (2) | 0.00076 (16) | 0.00055 (16) | 0.00022 (15) |
O3 | 0.0262 (3) | 0.01100 (19) | 0.00868 (19) | −0.00197 (17) | −0.00171 (17) | 0.00046 (14) |
C3 | 0.0155 (2) | 0.0115 (2) | 0.0098 (2) | −0.00032 (17) | 0.00033 (19) | 0.00107 (18) |
O4 | 0.0254 (3) | 0.00895 (18) | 0.0134 (2) | −0.00066 (17) | 0.00003 (18) | −0.00244 (16) |
C4 | 0.0160 (2) | 0.0149 (3) | 0.0090 (2) | −0.0014 (2) | 0.00129 (19) | −0.00155 (18) |
C5 | 0.0146 (2) | 0.0123 (2) | 0.0119 (2) | −0.00104 (18) | 0.00137 (19) | −0.00284 (18) |
O5 | 0.0235 (2) | 0.01238 (19) | 0.00926 (18) | 0.00303 (17) | −0.00269 (16) | −0.00188 (15) |
O6 | 0.0257 (3) | 0.01043 (18) | 0.0140 (2) | −0.00018 (17) | −0.00106 (19) | 0.00247 (16) |
C6 | 0.0147 (2) | 0.0087 (2) | 0.0112 (2) | 0.00105 (17) | 0.00180 (18) | −0.00041 (16) |
C7 | 0.0149 (2) | 0.0095 (2) | 0.0088 (2) | −0.00018 (17) | −0.00033 (17) | −0.00063 (16) |
O7 | 0.0211 (2) | 0.01177 (18) | 0.00942 (18) | 0.00354 (17) | 0.00307 (16) | 0.00203 (14) |
O8 | 0.0246 (2) | 0.00936 (17) | 0.01017 (18) | 0.00046 (16) | −0.00411 (18) | −0.00161 (15) |
C8 | 0.0129 (2) | 0.0090 (2) | 0.0084 (2) | −0.00027 (16) | −0.00043 (16) | −0.00028 (15) |
C9 | 0.0154 (2) | 0.0113 (2) | 0.0091 (2) | −0.00031 (18) | 0.00018 (17) | −0.00114 (17) |
O9 | 0.0231 (2) | 0.01198 (19) | 0.01149 (19) | 0.00270 (18) | 0.00054 (17) | 0.00284 (16) |
C10 | 0.0156 (2) | 0.0134 (2) | 0.0089 (2) | 0.00050 (18) | 0.00061 (19) | 0.00089 (18) |
O10 | 0.0222 (2) | 0.01103 (18) | 0.00970 (18) | 0.00224 (17) | 0.00031 (16) | 0.00134 (14) |
C11 | 0.0143 (2) | 0.0114 (2) | 0.0110 (2) | 0.00107 (18) | 0.00054 (18) | 0.00195 (17) |
C12 | 0.0154 (2) | 0.0088 (2) | 0.0095 (2) | −0.00066 (17) | −0.00140 (18) | −0.00056 (16) |
C13 | 0.0126 (2) | 0.0105 (2) | 0.00843 (19) | 0.00008 (16) | −0.00084 (17) | −0.00004 (17) |
C14 | 0.0131 (2) | 0.0110 (2) | 0.0096 (2) | −0.00061 (16) | −0.00037 (17) | 0.00152 (18) |
C15 | 0.0157 (2) | 0.0156 (3) | 0.0085 (2) | −0.0008 (2) | 0.00000 (18) | 0.00107 (19) |
C16 | 0.0172 (3) | 0.0162 (3) | 0.0090 (2) | −0.0001 (2) | 0.00149 (19) | −0.00142 (19) |
C17 | 0.0162 (2) | 0.0120 (2) | 0.0104 (2) | 0.00054 (18) | 0.00199 (19) | −0.00148 (18) |
C18 | 0.0127 (2) | 0.0103 (2) | 0.00860 (18) | 0.00042 (16) | 0.00097 (17) | 0.00027 (17) |
C19 | 0.0125 (2) | 0.0095 (2) | 0.0087 (2) | 0.00006 (16) | −0.00072 (16) | −0.00031 (15) |
C20 | 0.0126 (2) | 0.0116 (2) | 0.0089 (2) | 0.00133 (17) | −0.00060 (16) | 0.00054 (17) |
C21 | 0.0174 (3) | 0.0169 (3) | 0.0091 (2) | 0.0040 (2) | −0.00108 (19) | −0.00193 (19) |
C22 | 0.0202 (3) | 0.0153 (3) | 0.0122 (2) | 0.0041 (2) | −0.0023 (2) | −0.0045 (2) |
C23 | 0.0173 (3) | 0.0107 (2) | 0.0130 (2) | 0.00187 (19) | −0.0010 (2) | −0.00283 (18) |
C24 | 0.0127 (2) | 0.0094 (2) | 0.0094 (2) | 0.00024 (17) | −0.00003 (16) | −0.00045 (16) |
Geometric parameters (Å, º) top
O1—C6 | 1.2672 (10) | C8—C9 | 1.3951 (10) |
N1—H1 | 0.8800 | C8—C12 | 1.5128 (10) |
N1—C1 | 1.3429 (9) | C9—H9A | 0.9500 |
N1—C5 | 1.3419 (10) | C9—C10 | 1.3945 (10) |
C1—H1A | 0.9500 | O9—H9 | 0.83 (2) |
C1—C2 | 1.3859 (9) | O9—C20 | 1.3751 (9) |
O2—C6 | 1.2525 (10) | C10—H10A | 0.9500 |
N2—H2 | 0.8800 | C10—C11 | 1.3829 (11) |
N2—C7 | 1.3436 (9) | O10—H10 | 0.818 (18) |
N2—C11 | 1.3450 (10) | O10—C24 | 1.3599 (9) |
C2—C3 | 1.3946 (10) | C11—H11 | 0.9500 |
C2—C6 | 1.5079 (10) | C13—C14 | 1.4012 (10) |
O3—C12 | 1.2703 (9) | C13—C18 | 1.4020 (9) |
C3—H3 | 0.9500 | C14—C15 | 1.3960 (10) |
C3—C4 | 1.3926 (10) | C15—H15 | 0.9500 |
O4—C12 | 1.2481 (9) | C15—C16 | 1.3942 (11) |
C4—H4 | 0.9500 | C16—H16 | 0.9500 |
C4—C5 | 1.3835 (11) | C16—C17 | 1.3938 (11) |
C5—H5A | 0.9500 | C17—H17 | 0.9500 |
O5—H5 | 0.812 (18) | C17—C18 | 1.3906 (10) |
O5—C13 | 1.3611 (9) | C19—C20 | 1.3945 (10) |
O6—H6 | 0.77 (2) | C19—C24 | 1.4010 (9) |
O6—C14 | 1.3704 (9) | C20—C21 | 1.3962 (10) |
C7—H7A | 0.9500 | C21—H21 | 0.9500 |
C7—C8 | 1.3897 (10) | C21—C22 | 1.3924 (12) |
O7—H7 | 0.80 (2) | C22—H22 | 0.9500 |
O7—C18 | 1.3733 (9) | C22—C23 | 1.3960 (12) |
O8—H8 | 0.81 (2) | C23—H23 | 0.9500 |
O8—C19 | 1.3655 (9) | C23—C24 | 1.3918 (10) |
| | | |
C1—N1—H1 | 118.9 | N2—C11—C10 | 120.27 (7) |
C5—N1—H1 | 118.9 | N2—C11—H11 | 119.9 |
C5—N1—C1 | 122.23 (6) | C10—C11—H11 | 119.9 |
N1—C1—H1A | 119.9 | O3—C12—C8 | 116.99 (6) |
N1—C1—C2 | 120.18 (7) | O4—C12—O3 | 125.40 (7) |
C2—C1—H1A | 119.9 | O4—C12—C8 | 117.60 (7) |
C7—N2—H2 | 118.9 | O5—C13—C14 | 124.26 (6) |
C7—N2—C11 | 122.16 (7) | O5—C13—C18 | 116.90 (6) |
C11—N2—H2 | 118.9 | C14—C13—C18 | 118.80 (6) |
C1—C2—C3 | 118.52 (6) | O6—C14—C13 | 116.96 (6) |
C1—C2—C6 | 120.81 (6) | O6—C14—C15 | 122.85 (7) |
C3—C2—C6 | 120.66 (6) | C15—C14—C13 | 120.19 (6) |
C2—C3—H3 | 119.9 | C14—C15—H15 | 119.9 |
C4—C3—C2 | 120.17 (6) | C16—C15—C14 | 120.21 (7) |
C4—C3—H3 | 119.9 | C16—C15—H15 | 119.9 |
C3—C4—H4 | 120.7 | C15—C16—H16 | 119.9 |
C5—C4—C3 | 118.61 (7) | C17—C16—C15 | 120.14 (7) |
C5—C4—H4 | 120.7 | C17—C16—H16 | 119.9 |
N1—C5—C4 | 120.29 (7) | C16—C17—H17 | 120.2 |
N1—C5—H5A | 119.9 | C18—C17—C16 | 119.50 (7) |
C4—C5—H5A | 119.9 | C18—C17—H17 | 120.2 |
C13—O5—H5 | 109.5 | O7—C18—C13 | 120.05 (6) |
C14—O6—H6 | 109.5 | O7—C18—C17 | 118.80 (6) |
O1—C6—C2 | 117.56 (6) | C17—C18—C13 | 121.15 (6) |
O2—C6—O1 | 125.25 (7) | O8—C19—C20 | 118.70 (6) |
O2—C6—C2 | 117.17 (7) | O8—C19—C24 | 121.73 (6) |
N2—C7—H7A | 119.9 | C20—C19—C24 | 119.57 (6) |
N2—C7—C8 | 120.16 (7) | O9—C20—C19 | 121.02 (6) |
C8—C7—H7A | 119.9 | O9—C20—C21 | 118.61 (7) |
C18—O7—H7 | 109.5 | C19—C20—C21 | 120.37 (7) |
C19—O8—H8 | 109.5 | C20—C21—H21 | 120.3 |
C7—C8—C9 | 118.59 (6) | C22—C21—C20 | 119.34 (7) |
C7—C8—C12 | 120.15 (6) | C22—C21—H21 | 120.3 |
C9—C8—C12 | 121.26 (6) | C21—C22—H22 | 119.5 |
C8—C9—H9A | 120.0 | C21—C22—C23 | 121.03 (7) |
C10—C9—C8 | 120.00 (7) | C23—C22—H22 | 119.5 |
C10—C9—H9A | 120.0 | C22—C23—H23 | 120.4 |
C20—O9—H9 | 109.5 | C24—C23—C22 | 119.15 (7) |
C9—C10—H10A | 120.6 | C24—C23—H23 | 120.4 |
C11—C10—C9 | 118.79 (7) | O10—C24—C19 | 114.88 (6) |
C11—C10—H10A | 120.6 | O10—C24—C23 | 124.59 (7) |
C24—O10—H10 | 109.5 | C23—C24—C19 | 120.53 (7) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3 | 0.88 | 1.79 | 2.6706 (9) | 175 |
N1—H1···O4 | 0.88 | 2.60 | 3.2095 (10) | 126 |
C1—H1A···O4 | 0.95 | 2.60 | 3.2196 (10) | 123 |
N2—H2···O1i | 0.88 | 1.84 | 2.7127 (9) | 172 |
N2—H2···O2i | 0.88 | 2.57 | 3.1989 (10) | 129 |
C5—H5A···O4ii | 0.95 | 2.39 | 3.0356 (10) | 124 |
C5—H5A···O8i | 0.95 | 2.62 | 3.1303 (9) | 114 |
O5—H5···O4 | 0.81 | 2.00 | 2.6859 (9) | 142 |
O6—H6···O9iii | 0.77 | 2.21 | 2.9710 (9) | 171 |
C7—H7A···O10i | 0.95 | 2.48 | 3.3137 (10) | 146 |
O7—H7···O1 | 0.80 | 2.04 | 2.7050 (9) | 139 |
O8—H8···O3iv | 0.81 | 2.03 | 2.7508 (9) | 148 |
O9—H9···O7v | 0.83 | 2.05 | 2.8152 (9) | 151 |
O10—H10···O2 | 0.82 | 1.86 | 2.6353 (9) | 157 |
C11—H11···O2vi | 0.95 | 2.55 | 3.1478 (10) | 121 |
C21—H21···O10v | 0.95 | 2.50 | 3.2760 (10) | 138 |
Symmetry codes: (i) x, y−1, z; (ii) −x+3/2, y, z−1/2; (iii) x, y−1, z+1; (iv) x, y+1, z; (v) −x+1, −y+2, z−1/2; (vi) −x+3/2, y−1, z+1/2. |
Crystal data top
C24H22N2O10 | c = 12.9678 (4) Å |
Mr = 498.42 | V = 2114.40 (10) Å3 |
Orthorhombic, Pca21 | Z = 4 |
Hall symbol: P ? | F(000) = 1040 |
a = 13.6648 (4) Å | Dx = 1.566 Mg m−3 |
b = 11.9321 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
Data collection top
Radiation source: fine-focus sealed tube | h = 0→30 |
24319 independent reflections | k = 0→26 |
24319 reflections with > 2.0σ(I) | l = −28→28 |
θmax = 52.2°, θmin = 1.7° | |
Refinement top
Refinement on F | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.005 | H-atom parameters constrained |
wR(F2) = 0.005 | Weighting scheme based on measured s.u.'s |
S = 0.09 | (Δ/σ)max = −0.193 |
24319 reflections | Δρmax = 0.15 e Å−3 |
707 parameters | Δρmin = −0.12 e Å−3 |
0 restraints | Absolute structure: Rogers (1981), 11836 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Rogers parameter: 1 |
Special details top
Refinement. Refinement of F1 against reflections.
The threshold expression of F2 > 2sigma(F2) is
used for calculating R-factors(gt) and is not
relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice
as large as those based on F, and R-factors based on
ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.68089 | 0.64338 | 0.59216 | 0 | |
N1 | 0.68879 | 0.35067 | 0.42022 | 0 | |
H1 | 0.68542 | 0.26970 | 0.45767 | 0 | |
C1 | 0.68310 | 0.44394 | 0.47777 | 0 | |
H1A | 0.67264 | 0.43149 | 0.55994 | 0 | |
O2 | 0.68751 | 0.74535 | 0.44775 | 0 | |
N2 | 0.67968 | −0.14699 | 0.67341 | 0 | |
H2 | 0.68142 | −0.22544 | 0.63292 | 0 | |
C2 | 0.68699 | 0.54859 | 0.43124 | 0 | |
O3 | 0.68262 | 0.14656 | 0.50446 | 0 | |
C3 | 0.69545 | 0.55391 | 0.32407 | 0 | |
H3 | 0.69961 | 0.63472 | 0.28540 | 0 | |
O4 | 0.67793 | 0.24873 | 0.64886 | 0 | |
C4 | 0.70137 | 0.45578 | 0.26628 | 0 | |
H4 | 0.71005 | 0.46010 | 0.18309 | 0 | |
C5 | 0.69796 | 0.35402 | 0.31714 | 0 | |
H5 | 0.70276 | 0.27447 | 0.27700 | 0 | |
O5 | 0.56142 | 0.40687 | 0.73084 | 0 | |
H5A | 0.59770 | 0.33497 | 0.72808 | 0 | |
O6 | 0.58031 | 0.28227 | 0.91177 | 0 | |
H6 | 0.57567 | 0.25490 | 0.98322 | 0 | |
C6 | 0.68413 | 0.65409 | 0.49492 | 0 | |
C7 | 0.68004 | −0.05258 | 0.61693 | 0 | |
H7 | 0.68028 | −0.06381 | 0.53381 | 0 | |
O7 | 0.54118 | 0.63227 | 0.73962 | 0 | |
H7A | 0.57965 | 0.59878 | 0.68262 | 0 | |
O8 | 0.57046 | 1.13640 | 0.32854 | 0 | |
H8 | 0.59802 | 1.10558 | 0.39316 | 0 | |
C8 | 0.67825 | 0.05126 | 0.66529 | 0 | |
C9 | 0.67576 | 0.05491 | 0.77276 | 0 | |
H9 | 0.67291 | 0.13636 | 0.81048 | 0 | |
O9 | 0.54934 | 1.19663 | 0.12436 | 0 | |
H9A | 0.52812 | 1.24270 | 0.18345 | 0 | |
C10 | 0.67775 | −0.04442 | 0.82949 | 0 | |
H10 | 0.67840 | −0.04237 | 0.91312 | 0 | |
O10 | 0.58559 | 0.91926 | 0.38292 | 0 | |
H10A | 0.61285 | 0.84288 | 0.39514 | 0 | |
C11 | 0.67917 | −0.14552 | 0.77705 | 0 | |
H11 | 0.68115 | −0.22717 | 0.81377 | 0 | |
C12 | 0.67900 | 0.15754 | 0.60179 | 0 | |
C13 | 0.56219 | 0.45555 | 0.82561 | 0 | |
C14 | 0.57020 | 0.39610 | 0.91852 | 0 | |
C15 | 0.56854 | 0.45320 | 1.01247 | 0 | |
H15 | 0.57417 | 0.40514 | 1.08339 | 0 | |
C16 | 0.55733 | 0.56933 | 1.01458 | 0 | |
H16 | 0.55363 | 0.61002 | 1.08941 | 0 | |
C17 | 0.54836 | 0.62918 | 0.92287 | 0 | |
H17 | 0.53691 | 0.71936 | 0.92107 | 0 | |
C18 | 0.55110 | 0.57225 | 0.82929 | 0 | |
C19 | 0.56857 | 1.05467 | 0.25473 | 0 | |
C20 | 0.55770 | 1.08588 | 0.15179 | 0 | |
C21 | 0.55608 | 1.00477 | 0.07452 | 0 | |
H21 | 0.54382 | 1.03094 | −0.00484 | 0 | |
C22 | 0.56524 | 0.89209 | 0.10087 | 0 | |
H22 | 0.56226 | 0.82760 | 0.04160 | 0 | |
C23 | 0.57463 | 0.85923 | 0.20385 | 0 | |
H23 | 0.58124 | 0.77089 | 0.22372 | 0 | |
C24 | 0.57652 | 0.94092 | 0.28045 | 0 | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0 | 0 | 0 | 0 | 0 | 0 |
N1 | 0 | 0 | 0 | 0 | 0 | 0 |
H1 | 0 | 0 | 0 | 0 | 0 | 0 |
C1 | 0 | 0 | 0 | 0 | 0 | 0 |
H1A | 0 | 0 | 0 | 0 | 0 | 0 |
O2 | 0 | 0 | 0 | 0 | 0 | 0 |
N2 | 0 | 0 | 0 | 0 | 0 | 0 |
H2 | 0 | 0 | 0 | 0 | 0 | 0 |
C2 | 0 | 0 | 0 | 0 | 0 | 0 |
O3 | 0 | 0 | 0 | 0 | 0 | 0 |
C3 | 0 | 0 | 0 | 0 | 0 | 0 |
H3 | 0 | 0 | 0 | 0 | 0 | 0 |
O4 | 0 | 0 | 0 | 0 | 0 | 0 |
C4 | 0 | 0 | 0 | 0 | 0 | 0 |
H4 | 0 | 0 | 0 | 0 | 0 | 0 |
C5 | 0 | 0 | 0 | 0 | 0 | 0 |
H5 | 0 | 0 | 0 | 0 | 0 | 0 |
O5 | 0 | 0 | 0 | 0 | 0 | 0 |
H5A | 0 | 0 | 0 | 0 | 0 | 0 |
O6 | 0 | 0 | 0 | 0 | 0 | 0 |
H6 | 0 | 0 | 0 | 0 | 0 | 0 |
C6 | 0 | 0 | 0 | 0 | 0 | 0 |
C7 | 0 | 0 | 0 | 0 | 0 | 0 |
H7 | 0 | 0 | 0 | 0 | 0 | 0 |
O7 | 0 | 0 | 0 | 0 | 0 | 0 |
H7A | 0 | 0 | 0 | 0 | 0 | 0 |
O8 | 0 | 0 | 0 | 0 | 0 | 0 |
H8 | 0 | 0 | 0 | 0 | 0 | 0 |
C8 | 0 | 0 | 0 | 0 | 0 | 0 |
C9 | 0 | 0 | 0 | 0 | 0 | 0 |
H9 | 0 | 0 | 0 | 0 | 0 | 0 |
O9 | 0 | 0 | 0 | 0 | 0 | 0 |
H9A | 0 | 0 | 0 | 0 | 0 | 0 |
C10 | 0 | 0 | 0 | 0 | 0 | 0 |
H10 | 0 | 0 | 0 | 0 | 0 | 0 |
O10 | 0 | 0 | 0 | 0 | 0 | 0 |
H10A | 0 | 0 | 0 | 0 | 0 | 0 |
C11 | 0 | 0 | 0 | 0 | 0 | 0 |
H11 | 0 | 0 | 0 | 0 | 0 | 0 |
C12 | 0 | 0 | 0 | 0 | 0 | 0 |
C13 | 0 | 0 | 0 | 0 | 0 | 0 |
C14 | 0 | 0 | 0 | 0 | 0 | 0 |
C15 | 0 | 0 | 0 | 0 | 0 | 0 |
H15 | 0 | 0 | 0 | 0 | 0 | 0 |
C16 | 0 | 0 | 0 | 0 | 0 | 0 |
H16 | 0 | 0 | 0 | 0 | 0 | 0 |
C17 | 0 | 0 | 0 | 0 | 0 | 0 |
H17 | 0 | 0 | 0 | 0 | 0 | 0 |
C18 | 0 | 0 | 0 | 0 | 0 | 0 |
C19 | 0 | 0 | 0 | 0 | 0 | 0 |
C20 | 0 | 0 | 0 | 0 | 0 | 0 |
C21 | 0 | 0 | 0 | 0 | 0 | 0 |
H21 | 0 | 0 | 0 | 0 | 0 | 0 |
C22 | 0 | 0 | 0 | 0 | 0 | 0 |
H22 | 0 | 0 | 0 | 0 | 0 | 0 |
C23 | 0 | 0 | 0 | 0 | 0 | 0 |
H23 | 0 | 0 | 0 | 0 | 0 | 0 |
C24 | 0 | 0 | 0 | 0 | 0 | 0 |
Geometric parameters (Å, º) top
O1—C6 | 1.2682 | C8—C12 | 1.5120 |
N1—C1 | 1.3421 | C8—C9 | 1.3948 |
N1—C5 | 1.3432 | C9—C10 | 1.3953 |
N1—H1 | 1.0824 | C9—H9 | 1.0887 |
C1—C2 | 1.3879 | O9—C20 | 1.3733 |
C1—H1A | 1.0854 | O9—H9A | 0.9866 |
O2—C6 | 1.2498 | C10—C11 | 1.3848 |
N2—C7 | 1.3436 | C10—H10 | 1.0848 |
N2—C11 | 1.3441 | O10—C24 | 1.3593 |
N2—H2 | 1.0736 | O10—H10A | 0.9973 |
C2—C6 | 1.5061 | C11—H11 | 1.0848 |
C2—C3 | 1.3960 | C13—C18 | 1.4015 |
O3—C12 | 1.2700 | C13—C14 | 1.4025 |
C3—C4 | 1.3926 | C14—C15 | 1.3960 |
C3—H3 | 1.0883 | C15—C16 | 1.3944 |
O4—C12 | 1.2478 | C15—H15 | 1.0866 |
C4—C5 | 1.3826 | C16—C17 | 1.3926 |
C4—H4 | 1.0865 | C16—H16 | 1.0862 |
C5—H5 | 1.0845 | C17—C18 | 1.3913 |
O5—C13 | 1.3594 | C17—H17 | 1.0876 |
O5—H5A | 0.9914 | C19—C20 | 1.3938 |
O6—C14 | 1.3681 | C19—C24 | 1.4020 |
O6—H6 | 0.9845 | C20—C21 | 1.3933 |
C7—C8 | 1.3890 | C21—C22 | 1.3928 |
C7—H7 | 1.0862 | C21—H21 | 1.0885 |
O7—C18 | 1.3724 | C22—C23 | 1.3977 |
O7—H7A | 0.9912 | C22—H22 | 1.0884 |
O8—C19 | 1.3666 | C23—C24 | 1.3920 |
O8—H8 | 0.9896 | C23—H23 | 1.0889 |
| | | |
C1—N1—C5 | 122.279 | N2—C11—C10 | 120.159 |
C1—N1—H1 | 119.229 | N2—C11—H11 | 115.280 |
C5—N1—H1 | 118.490 | C10—C11—H11 | 124.553 |
N1—C1—C2 | 120.140 | O4—C12—O3 | 125.211 |
N1—C1—H1A | 116.106 | O4—C12—C8 | 117.703 |
C2—C1—H1A | 123.709 | O3—C12—C8 | 117.071 |
C7—N2—C11 | 122.285 | O5—C13—C18 | 117.040 |
C7—N2—H2 | 117.668 | O5—C13—C14 | 124.133 |
C11—N2—H2 | 120.033 | C18—C13—C14 | 118.795 |
C6—C2—C1 | 120.840 | O6—C14—C13 | 117.070 |
C6—C2—C3 | 120.668 | O6—C14—C15 | 122.822 |
C1—C2—C3 | 118.482 | C13—C14—C15 | 120.106 |
C2—C3—C4 | 120.154 | C14—C15—C16 | 120.260 |
C2—C3—H3 | 120.219 | C14—C15—H15 | 118.681 |
C4—C3—H3 | 119.603 | C16—C15—H15 | 121.039 |
C5—C4—C3 | 118.668 | C17—C16—C15 | 120.167 |
C5—C4—H4 | 121.270 | C17—C16—H16 | 121.976 |
C3—C4—H4 | 120.049 | C15—C16—H16 | 117.829 |
N1—C5—C4 | 120.269 | C18—C17—C16 | 119.480 |
N1—C5—H5 | 117.213 | C18—C17—H17 | 117.921 |
C4—C5—H5 | 122.518 | C16—C17—H17 | 122.571 |
C13—O5—H5A | 113.485 | O7—C18—C13 | 120.017 |
C14—O6—H6 | 105.222 | O7—C18—C17 | 118.791 |
O2—C6—O1 | 125.152 | C13—C18—C17 | 121.184 |
O2—C6—C2 | 117.313 | O8—C19—C20 | 118.825 |
O1—C6—C2 | 117.512 | O8—C19—C24 | 121.519 |
N2—C7—C8 | 120.115 | C20—C19—C24 | 119.655 |
N2—C7—H7 | 115.947 | O9—C20—C19 | 120.932 |
C8—C7—H7 | 123.926 | O9—C20—C21 | 118.743 |
C18—O7—H7A | 111.661 | C19—C20—C21 | 120.322 |
C19—O8—H8 | 109.579 | C20—C21—C22 | 119.517 |
C12—C8—C7 | 120.145 | C20—C21—H21 | 118.887 |
C12—C8—C9 | 121.208 | C22—C21—H21 | 121.517 |
C7—C8—C9 | 118.646 | C21—C22—C23 | 120.897 |
C8—C9—C10 | 119.985 | C21—C22—H22 | 120.389 |
C8—C9—H9 | 118.533 | C23—C22—H22 | 118.669 |
C10—C9—H9 | 121.479 | C24—C23—C22 | 119.147 |
C20—O9—H9A | 111.064 | C24—C23—H23 | 120.493 |
C11—C10—C9 | 118.775 | C22—C23—H23 | 120.356 |
C11—C10—H10 | 120.691 | O10—C24—C19 | 115.066 |
C9—C10—H10 | 120.533 | O10—C24—C23 | 124.485 |
C24—O10—H10A | 111.293 | C19—C24—C23 | 120.448 |
| | | |
O1—C6—C2—C1 | 1.97 | O7—C18—C13—C14 | −178.74 |
O1—C6—C2—C3 | −176.83 | O7—C18—C17—C16 | 179.36 |
N1—C1—C2—C6 | −177.93 | O7—C18—C17—H17 | 1.23 |
N1—C1—C2—C3 | 0.90 | H7A—O7—C18—C13 | −33.88 |
N1—C5—C4—C3 | 0.21 | H7A—O7—C18—C17 | 147.10 |
N1—C5—C4—H4 | 178.91 | O8—C19—C20—O9 | 0.23 |
H1—N1—C1—C2 | −179.81 | O8—C19—C20—C21 | 179.61 |
H1—N1—C1—H1A | −2.14 | O8—C19—C24—O10 | 0.30 |
H1—N1—C5—C4 | 179.24 | O8—C19—C24—C23 | −179.85 |
H1—N1—C5—H5 | −1.02 | H8—O8—C19—C20 | −162.99 |
C1—N1—C5—C4 | −0.34 | H8—O8—C19—C24 | 17.52 |
C1—N1—C5—H5 | 179.40 | C8—C7—N2—C11 | −1.08 |
C1—C2—C6—O2 | −179.71 | C8—C9—C10—C11 | −1.95 |
C1—C2—C3—C4 | −1.01 | C8—C9—C10—H10 | 177.85 |
C1—C2—C3—H3 | −179.22 | C9—C10—C11—H11 | 179.65 |
H1A—C1—N1—C5 | 177.43 | H9—C9—C8—C12 | 1.19 |
H1A—C1—C2—C6 | 4.59 | H9—C9—C10—C11 | 178.59 |
H1A—C1—C2—C3 | −176.58 | H9—C9—C10—H10 | −1.61 |
O2—C6—C2—C3 | 1.49 | O9—C20—C19—C24 | 179.73 |
N2—C7—C8—C12 | 179.79 | O9—C20—C21—C22 | 179.49 |
N2—C7—C8—C9 | −0.20 | O9—C20—C21—H21 | −3.67 |
N2—C11—C10—C9 | 0.70 | H9A—O9—C20—C19 | −20.77 |
N2—C11—C10—H10 | −179.10 | H9A—O9—C20—C21 | 159.85 |
H2—N2—C7—C8 | −179.75 | C10—C9—C8—C12 | −178.29 |
H2—N2—C7—H7 | 1.45 | H10—C10—C11—H11 | −0.14 |
H2—N2—C11—C10 | 179.47 | O10—C24—C19—C20 | −179.19 |
H2—N2—C11—H11 | 0.42 | O10—C24—C23—C22 | −179.82 |
C2—C1—N1—C5 | −0.23 | O10—C24—C23—H23 | −0.53 |
C2—C3—C4—C5 | 0.47 | H10A—O10—C24—C19 | −160.94 |
C2—C3—C4—H4 | −178.25 | H10A—O10—C24—C23 | 19.21 |
O3—C12—C8—C7 | −0.90 | C13—C18—C17—C16 | 0.35 |
O3—C12—C8—C9 | 179.09 | C13—C18—C17—H17 | −177.78 |
C3—C4—C5—H5 | −179.50 | C13—C14—C15—C16 | 1.04 |
H3—C3—C2—C6 | −0.39 | C13—C14—C15—H15 | 179.43 |
H3—C3—C4—C5 | 178.69 | C14—C13—C18—C17 | 0.26 |
H3—C3—C4—H4 | −0.03 | C14—C15—C16—C17 | −0.42 |
O4—C12—C8—C7 | −179.57 | C14—C15—C16—H16 | 177.70 |
O4—C12—C8—C9 | 0.43 | C15—C14—C13—C18 | −0.95 |
C4—C3—C2—C6 | 177.82 | C15—C16—C17—C18 | −0.28 |
H4—C4—C5—H5 | −0.81 | C15—C16—C17—H17 | 177.77 |
O5—C13—C18—O7 | −0.72 | H15—C15—C16—C17 | −178.76 |
O5—C13—C18—C17 | 178.28 | H15—C15—C16—H16 | −0.65 |
O5—C13—C14—O6 | 1.73 | H16—C16—C17—C18 | −178.31 |
O5—C13—C14—C15 | −178.82 | H16—C16—C17—H17 | −0.27 |
H5A—O5—C13—C18 | 153.93 | C19—C20—C21—C22 | 0.11 |
H5A—O5—C13—C14 | −28.17 | C19—C20—C21—H21 | 176.95 |
O6—C14—C13—C18 | 179.60 | C19—C24—C23—C22 | 0.34 |
O6—C14—C15—C16 | −179.54 | C19—C24—C23—H23 | 179.63 |
O6—C14—C15—H15 | −1.16 | C20—C19—C24—C23 | 0.67 |
H6—O6—C14—C13 | −172.49 | C20—C21—C22—C23 | 0.92 |
H6—O6—C14—C15 | 8.08 | C20—C21—C22—H22 | 178.44 |
C7—N2—C11—C10 | 0.83 | C21—C20—C19—C24 | −0.90 |
C7—N2—C11—H11 | −178.22 | C21—C22—C23—C24 | −1.15 |
C7—C8—C9—C10 | 1.70 | C21—C22—C23—H23 | 179.57 |
C7—C8—C9—H9 | −178.82 | H21—C21—C22—C23 | −175.83 |
H7—C7—N2—C11 | −179.88 | H21—C21—C22—H22 | 1.68 |
H7—C7—C8—C12 | −1.51 | H22—C22—C23—C24 | −178.70 |
H7—C7—C8—C9 | 178.49 | H22—C22—C23—H23 | 2.01 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O1i | 1.07 | 1.65 | 2.7142 | 169 |
N2—H2···O2i | 1.07 | 2.43 | 3.1977 | 128 |
N2—H2···C6i | 1.07 | 2.30 | 3.3158 | 158 |
C5—H5···O8i | 1.09 | 2.54 | 3.1305 | 114 |
C7—H7···O2i | 1.09 | 2.54 | 3.2615 | 123 |
C7—H7···O10i | 1.09 | 2.36 | 3.3148 | 147 |
O6—H6···O9ii | 0.98 | 1.99 | 2.9704 | 173 |
C15—H15···O9ii | 1.09 | 2.57 | 3.3980 | 133 |
N1—H1···O3 | 1.08 | 1.59 | 2.6705 | 176 |
N1—H1···O4 | 1.08 | 2.49 | 3.2082 | 123 |
N1—H1···C12 | 1.08 | 2.30 | 3.2974 | 152 |
C1—H1A···O4 | 1.09 | 2.47 | 3.2177 | 125 |
O5—H5A···O4 | 0.99 | 1.82 | 2.6880 | 144 |
O7—H7A···O1 | 0.99 | 1.89 | 2.7054 | 138 |
O8—H8···O10 | 0.99 | 2.23 | 2.6931 | 107 |
C9—H9···O6 | 1.09 | 2.52 | 3.5085 | 150 |
O9—H9A···O8 | 0.99 | 2.34 | 2.7587 | 105 |
O10—H10A···O2 | 1.00 | 1.69 | 2.6368 | 157 |
O8—H8···O3iii | 0.99 | 1.91 | 2.7510 | 141 |
C11—H11···O2iv | 1.09 | 2.52 | 3.1487 | 116 |
C5—H5···O4v | 1.09 | 2.35 | 3.0359 | 120 |
C15—H15···O7vi | 1.09 | 2.61 | 3.4590 | 135 |
C16—H16···O5vi | 1.09 | 2.42 | 3.2525 | 132 |
O9—H9A···O7vii | 0.99 | 1.91 | 2.8164 | 151 |
C21—H21···O10vii | 1.09 | 2.37 | 3.2776 | 140 |
C17—H17···O8viii | 1.09 | 2.56 | 3.4578 | 139 |
Symmetry codes: (i) x, y−1, z; (ii) x, y−1, z+1; (iii) x, y+1, z; (iv) −x+3/2, y−1, z+1/2; (v) −x+3/2, y, z−1/2; (vi) −x+1, −y+1, z+1/2; (vii) −x+1, −y+2, z−1/2; (viii) −x+1, −y+2, z+1/2. |