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Experimental electron density analysis by means of high-resolution X-ray diffraction data up to sinθ/λmax = 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520621009124/px5041sup1.cif
Contains datablocks IAM_MoPro, multipolar_MoPro, IAM_SHELX, theoretical

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520621009124/px5041IAM_MoProsup2.hkl
Contains datablock IAM_MoPro

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520621009124/px5041multipolar_MoProsup3.hkl
Contains datablock multipolar_MoPRO

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520621009124/px5041theoreticalsup4.hkl
Contains datablock theoretical

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520621009124/px5041sup5.pdf
Figures S1-S11 and Tables S1-S4.

CCDC references: 2107343; 2107344; 2107345

Computing details top

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.

(IAM_MoPro) top
Crystal data top
C6H5NO2·C6H6O3Dx = 1.566 Mg m3
Mr = 249.22Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21Cell parameters from 2780 reflections
a = 13.6648 (4) Åθ = 2.3–52.2°
b = 11.9321 (3) ŵ = 0.12 mm1
c = 12.9678 (4) ÅT = 100 K
V = 2114.40 (10) Å3Block, brown
Z = 80.35 × 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-focusRint = 0.051
ω and phi scanθmax = 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 = 3021
Tmin = 0.675, Tmax = 0.750k = 2624
24508 measured reflectionsl = 2828
19169 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046H-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 reflectionsΔρmax = 0.70 e Å3
325 parametersΔρmin = 0.51 e Å3
0 restraintsAbsolute structure: Rogers (1981), 8469 Friedel pairs
Primary atom site location: structure-invariant direct methodsRogers 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
xyzUiso*/Ueq
O10.68086 (4)0.64334 (5)0.547657 (10)0.01537 (2)
N10.68878 (4)0.35059 (4)0.37560 (6)0.01156 (2)
H10.686020.274970.411330.02558
C10.68304 (4)0.44404 (5)0.43321 (6)0.01069 (2)
H1A0.675330.437670.516120.02649
O20.68743 (5)0.74549 (5)0.40295 (6)0.01747 (2)
N20.67958 (4)0.14702 (5)0.62877 (6)0.01136 (2)
H20.679780.222110.591990.02593
C20.68697 (4)0.54854 (5)0.38668 (6)0.01017 (2)
O30.68257 (4)0.14659 (4)0.45986 (5)0.01527 (2)
C30.69543 (5)0.55387 (5)0.27945 (7)0.01227 (2)
H30.697390.634610.241350.02621
O40.67781 (4)0.24890 (5)0.60435 (6)0.01594 (2)
C40.70137 (5)0.45585 (6)0.22167 (7)0.01336 (2)
H40.708430.459160.138540.02551
C50.69804 (5)0.35394 (5)0.27265 (7)0.01292 (2)
H50.702910.276600.229240.02345
O50.56140 (4)0.40688 (4)0.68618 (6)0.01504 (2)
H5A0.598020.336310.688520.02559
O60.58033 (4)0.28203 (4)0.86706 (6)0.01667 (2)
H60.578190.249300.936330.02326
C60.68415 (5)0.65410 (5)0.45040 (7)0.01160 (2)
C70.67999 (5)0.05243 (5)0.57228 (6)0.01110 (2)
H70.681640.057480.488910.02381
O70.54114 (4)0.63229 (4)0.69501 (6)0.01416 (2)
H7A0.580890.597710.640750.02620
O80.57053 (4)1.13640 (4)0.28397 (6)0.01463 (2)
H80.602551.107620.346190.02487
C80.67814 (4)0.05134 (5)0.62073 (6)0.01012 (2)
C90.67581 (5)0.05484 (5)0.72827 (7)0.01201 (2)
H90.672540.134760.767710.02486
O90.54926 (4)1.19674 (5)0.07979 (6)0.01550 (2)
H9A0.528311.240720.139670.02641
C100.67769 (5)0.04451 (5)0.78492 (7)0.01266 (2)
H100.677950.042500.868410.02400
O100.58565 (4)0.91944 (4)0.33841 (6)0.01431 (2)
H10A0.613520.844490.348040.02639
C110.67913 (5)0.14542 (5)0.73257 (7)0.01223 (2)
H110.679910.223460.775220.02658
C120.67900 (5)0.15763 (5)0.55721 (7)0.01127 (2)
C130.56224 (4)0.45555 (5)0.78110 (7)0.01050 (2)
C140.57031 (4)0.39610 (5)0.87395 (7)0.01132 (2)
C150.56852 (5)0.45306 (6)0.96802 (7)0.01318 (2)
H150.575850.406941.039540.02636
C160.55728 (5)0.56925 (6)0.97010 (7)0.01411 (3)
H160.555450.613001.043240.02659
C170.54835 (5)0.62906 (5)0.87836 (7)0.01290 (2)
H170.539260.719210.879830.02712
C180.55112 (4)0.57223 (5)0.78478 (7)0.01057 (2)
C190.56861 (4)1.05463 (5)0.21022 (6)0.01017 (2)
C200.55772 (4)1.08576 (5)0.10733 (7)0.01098 (2)
C210.55609 (5)1.00464 (6)0.02978 (7)0.01425 (3)
H210.547681.029010.050180.02647
C220.56525 (5)0.89210 (6)0.05631 (7)0.01582 (3)
H220.565290.828990.003710.02600
C230.57457 (5)0.85924 (5)0.15926 (7)0.01369 (2)
H230.580330.771330.179150.02656
C240.57653 (4)0.94088 (5)0.23588 (7)0.01049 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0243 (2)0.01114 (17)0.01064 (17)0.00074 (14)0.00434 (15)0.00181 (13)
N10.01403 (16)0.00894 (16)0.01171 (17)0.00040 (12)0.00030 (14)0.00081 (13)
H10.038950.017010.020770.000080.001270.00250
C10.01405 (19)0.00871 (18)0.00931 (17)0.00010 (14)0.00013 (14)0.00005 (14)
H1A0.039800.024920.014730.000400.002130.00041
O20.0267 (2)0.00858 (16)0.0171 (2)0.00236 (15)0.00211 (17)0.00226 (14)
N20.01452 (18)0.00911 (16)0.01043 (17)0.00083 (13)0.00008 (13)0.00020 (13)
H20.038770.017140.021870.000730.000550.00296
C20.01268 (17)0.00885 (17)0.00897 (17)0.00076 (13)0.00055 (13)0.00032 (13)
O30.0261 (2)0.01096 (17)0.00878 (15)0.00198 (15)0.00167 (14)0.00048 (12)
C30.01538 (19)0.0117 (2)0.00973 (18)0.00020 (15)0.00025 (16)0.00120 (15)
H30.039080.017260.022290.000490.000650.00380
O40.0258 (2)0.00874 (15)0.01332 (17)0.00051 (15)0.00021 (15)0.00238 (13)
C40.0160 (2)0.0147 (2)0.00942 (18)0.00140 (17)0.00121 (16)0.00154 (16)
H40.036770.025220.014550.000460.001260.00000
C50.01462 (19)0.0124 (2)0.0117 (2)0.00106 (15)0.00122 (15)0.00260 (16)
H50.030250.018990.021100.004940.000720.00064
O50.0237 (2)0.01214 (16)0.00931 (15)0.00291 (14)0.00265 (14)0.00175 (13)
H5A0.036990.017900.021870.000930.000870.00484
O60.0253 (2)0.01035 (16)0.01441 (18)0.00019 (15)0.00086 (16)0.00238 (14)
H60.031710.021530.016540.000300.001230.00207
C60.01474 (19)0.00867 (18)0.01138 (19)0.00103 (14)0.00199 (15)0.00032 (14)
C70.0148 (2)0.00941 (18)0.00906 (17)0.00002 (14)0.00041 (14)0.00050 (14)
H70.030500.022590.018340.004740.003700.00120
O70.02105 (19)0.01195 (16)0.00948 (15)0.00349 (14)0.00309 (13)0.00212 (12)
H7A0.038270.024920.015420.000220.000070.00079
O80.0244 (2)0.00914 (15)0.01038 (15)0.00040 (13)0.00383 (15)0.00146 (13)
H80.034400.021450.018740.004120.004330.00058
C80.01295 (18)0.00882 (17)0.00858 (17)0.00023 (14)0.00049 (13)0.00023 (13)
C90.0157 (2)0.01124 (19)0.00905 (18)0.00025 (15)0.00012 (15)0.00124 (15)
H90.035230.020410.018950.003520.002060.00199
O90.0228 (2)0.01210 (17)0.01160 (16)0.00234 (15)0.00050 (14)0.00303 (13)
H9A0.039030.017560.022630.000320.000760.00407
C100.0158 (2)0.0134 (2)0.00884 (17)0.00060 (15)0.00067 (15)0.00079 (16)
H100.033390.017740.020850.005060.000270.00034
O100.02229 (19)0.01115 (16)0.00950 (15)0.00196 (14)0.00033 (14)0.00129 (12)
H10A0.038450.025380.015350.000710.000090.00011
C110.01425 (19)0.01153 (19)0.0109 (2)0.00115 (15)0.00053 (15)0.00190 (15)
H110.038620.017880.023240.000890.000430.00466
C120.01537 (19)0.00888 (18)0.00957 (17)0.00059 (14)0.00136 (15)0.00045 (14)
C130.01265 (17)0.01040 (18)0.00845 (16)0.00014 (13)0.00084 (14)0.00005 (14)
C140.01310 (18)0.01128 (18)0.00959 (17)0.00047 (14)0.00041 (14)0.00160 (15)
C150.0156 (2)0.0154 (2)0.00860 (18)0.00070 (17)0.00002 (15)0.00107 (16)
H150.037690.024080.017310.001640.000690.00415
C160.0173 (2)0.0161 (2)0.00891 (18)0.00026 (17)0.00134 (16)0.00136 (16)
H160.038360.024480.016930.001920.000200.00470
C170.0160 (2)0.01226 (19)0.01043 (18)0.00023 (16)0.00197 (16)0.00155 (16)
H170.040210.016600.024570.003380.000030.00083
C180.01268 (17)0.01020 (17)0.00883 (16)0.00045 (14)0.00112 (14)0.00006 (14)
C190.01243 (17)0.00948 (17)0.00861 (17)0.00009 (13)0.00086 (13)0.00036 (13)
C200.01230 (17)0.01156 (19)0.00907 (16)0.00131 (15)0.00070 (14)0.00055 (15)
C210.0170 (2)0.0166 (2)0.00916 (18)0.00398 (18)0.00117 (15)0.00189 (16)
H210.038130.025200.016080.002210.001740.00266
C220.0200 (2)0.0153 (2)0.0121 (2)0.00426 (19)0.00217 (18)0.00439 (18)
H220.037320.021020.019650.001790.000330.00504
C230.0174 (2)0.0108 (2)0.0129 (2)0.00195 (16)0.00102 (17)0.00289 (16)
H230.039350.016170.024150.002330.000570.00205
C240.01267 (17)0.00932 (17)0.00948 (17)0.00018 (14)0.00001 (14)0.00048 (14)
Geometric parameters (Å, º) top
O1—C61.2685 (9)C8—C121.5123 (8)
N1—C11.3444 (8)C8—C91.3956 (8)
N1—C51.3416 (9)C9—C101.3948 (9)
N1—H11.0150C9—H91.0830
C1—C21.3863 (8)O9—C201.3763 (8)
C1—H1A1.0830O9—H9A0.9800
O2—C61.2529 (8)C10—C111.3825 (9)
N2—C71.3455 (8)C10—H101.0830
N2—C111.3463 (8)O10—C241.3597 (8)
N2—H21.0150O10—H10A0.9800
C2—C61.5068 (9)C11—H111.0830
C2—C31.3968 (9)C13—C181.4013 (8)
O3—C121.2702 (8)C13—C141.4019 (8)
C3—C41.3914 (9)C14—C151.3967 (9)
C3—H31.0830C15—C161.3951 (10)
O4—C121.2490 (8)C15—H151.0830
C4—C51.3849 (10)C16—C171.3927 (10)
C4—H41.0830C16—H161.0830
C5—H51.0830C17—C181.3907 (9)
O5—C131.3611 (8)C17—H171.0830
O5—H5A0.9800C19—C201.3930 (8)
O6—C141.3709 (8)C19—C241.4016 (8)
O6—H60.9800C20—C211.3960 (9)
C7—C81.3887 (8)C21—C221.3919 (11)
C7—H71.0830C21—H211.0830
O7—C181.3739 (8)C22—C231.3972 (10)
O7—H7A0.9800C22—H221.0830
O8—C191.3665 (8)C23—C241.3917 (9)
O8—H80.9800C23—H231.0830
C1—N1—C5122.26 (5)N2—C11—C10120.22 (5)
C1—N1—H1118.78 (5)N2—C11—H11119.89 (6)
C5—N1—H1118.96 (6)C10—C11—H11119.89 (5)
N1—C1—C2120.13 (5)O4—C12—O3125.27 (5)
N1—C1—H1A119.95 (5)O4—C12—C8117.68 (5)
C2—C1—H1A119.93 (5)O3—C12—C8117.04 (5)
C7—N2—C11122.18 (5)O5—C13—C18116.99 (5)
C7—N2—H2118.99 (5)O5—C13—C14124.16 (5)
C11—N2—H2118.83 (6)C18—C13—C14118.81 (5)
C6—C2—C1120.81 (5)O6—C14—C13117.02 (5)
C6—C2—C3120.66 (5)O6—C14—C15122.81 (5)
C1—C2—C3118.52 (5)C13—C14—C15120.17 (5)
C2—C3—C4120.18 (5)C14—C15—C16120.15 (5)
C2—C3—H3119.79 (6)C14—C15—H15119.94 (6)
C4—C3—H3120.04 (5)C16—C15—H15119.91 (5)
C5—C4—C3118.63 (5)C17—C16—C15120.16 (6)
C5—C4—H4120.67 (5)C17—C16—H16119.94 (6)
C3—C4—H4120.70 (5)C15—C16—H16119.90 (5)
N1—C5—C4120.28 (5)C18—C17—C16119.54 (5)
N1—C5—H5119.85 (6)C18—C17—H17120.19 (6)
C4—C5—H5119.87 (5)C16—C17—H17120.27 (6)
C13—O5—H5A109.52 (5)O7—C18—C13120.01 (5)
C14—O6—H6109.45 (5)O7—C18—C17118.84 (5)
O2—C6—O1125.28 (6)C13—C18—C17121.15 (5)
O2—C6—C2117.21 (5)O8—C19—C20118.81 (5)
O1—C6—C2117.48 (5)O8—C19—C24121.59 (5)
N2—C7—C8120.10 (5)C20—C19—C24119.60 (5)
N2—C7—H7119.79 (5)O9—C20—C19120.94 (5)
C8—C7—H7120.11 (5)O9—C20—C21118.61 (5)
C18—O7—H7A109.50 (5)C19—C20—C21120.45 (5)
C19—O8—H8109.55 (5)C20—C21—C22119.30 (6)
C12—C8—C7120.08 (5)C20—C21—H21120.35 (6)
C12—C8—C9121.28 (5)C22—C21—H21120.35 (6)
C7—C8—C9118.64 (5)C21—C22—C23121.01 (6)
C8—C9—C10120.02 (5)C21—C22—H22119.55 (6)
C8—C9—H9119.95 (6)C23—C22—H22119.44 (6)
C10—C9—H9120.02 (5)C24—C23—C22119.17 (6)
C20—O9—H9A109.52 (5)C24—C23—H23120.43 (6)
C11—C10—C9118.81 (5)C22—C23—H23120.40 (6)
C11—C10—H10120.67 (5)O10—C24—C19114.92 (5)
C9—C10—H10120.52 (5)O10—C24—C23124.62 (5)
C24—O10—H10A109.39 (5)C19—C24—C23120.46 (5)
O1—C6—C2—C11.93 (9)O7—C18—C13—C14178.74 (8)
O1—C6—C2—C3176.88 (9)O7—C18—C17—C16179.30 (8)
N1—C1—C2—C6177.87 (8)O7—C18—C17—H170.65
N1—C1—C2—C30.96 (8)H7A—O7—C18—C1334.86
N1—C5—C4—C30.33 (8)H7A—O7—C18—C17146.16
N1—C5—C4—H4179.65O8—C19—C20—O90.17 (8)
H1—N1—C1—C2179.75O8—C19—C20—C21179.57 (8)
H1—N1—C1—H1A0.25O8—C19—C24—O100.27 (8)
H1—N1—C5—C4179.58O8—C19—C24—C23179.87 (9)
H1—N1—C5—H50.39H8—O8—C19—C20158.55
C1—N1—C5—C40.45 (8)H8—O8—C19—C2421.97
C1—N1—C5—H5179.58C8—C7—N2—C111.19 (9)
C1—C2—C6—O2179.60 (9)C8—C9—C10—C111.76 (9)
C1—C2—C3—C41.06 (9)C8—C9—C10—H10178.28
C1—C2—C3—H3178.97C9—C10—C11—H11179.42
H1A—C1—N1—C5179.78H9—C9—C8—C121.70
H1A—C1—C2—C62.14H9—C9—C10—C11178.24
H1A—C1—C2—C3179.03H9—C9—C10—H101.72
O2—C6—C2—C31.59 (9)O9—C20—C19—C24179.66 (8)
N2—C7—C8—C12179.76 (8)O9—C20—C21—C22179.56 (9)
N2—C7—C8—C90.03 (8)O9—C20—C21—H210.54
N2—C11—C10—C90.57 (8)H9A—O9—C20—C1920.60
N2—C11—C10—H10179.47H9A—O9—C20—C21159.99
H2—N2—C7—C8178.97C10—C9—C8—C12178.29 (9)
H2—N2—C7—H70.93H10—C10—C11—H110.54
H2—N2—C11—C10179.24O10—C24—C19—C20179.21 (8)
H2—N2—C11—H110.75O10—C24—C23—C22179.74 (9)
C2—C1—N1—C50.22 (8)O10—C24—C23—H230.15
C2—C3—C4—C50.43 (9)H10A—O10—C24—C19160.04
C2—C3—C4—H4179.59H10A—O10—C24—C2320.11
O3—C12—C8—C70.77 (9)C13—C18—C17—C160.33 (8)
O3—C12—C8—C9179.02 (9)C13—C18—C17—H17179.62
C3—C4—C5—H5179.69C13—C14—C15—C160.92 (8)
H3—C3—C2—C62.19C13—C14—C15—H15179.10
H3—C3—C4—C5179.60C14—C13—C18—C170.22 (8)
H3—C3—C4—H40.37C14—C15—C16—C170.36 (9)
O4—C12—C8—C7179.61 (9)C14—C15—C16—H16179.59
O4—C12—C8—C90.17 (9)C15—C14—C13—C180.84 (8)
C4—C3—C2—C6177.77 (9)C15—C16—C17—C180.26 (9)
H4—C4—C5—H50.33C15—C16—C17—H17179.69
O5—C13—C18—O70.74 (8)H15—C15—C16—C17179.65
O5—C13—C18—C17178.21 (8)H15—C15—C16—H160.39
O5—C13—C14—O61.66 (8)H16—C16—C17—C18179.79
O5—C13—C14—C15178.68 (8)H16—C16—C17—H170.27
H5A—O5—C13—C18154.23C19—C20—C21—C220.15 (9)
H5A—O5—C13—C1427.89C19—C20—C21—H21179.96
O6—C14—C13—C18179.51 (8)C19—C24—C23—C220.41 (9)
O6—C14—C15—C16179.45 (9)C19—C24—C23—H23179.70
O6—C14—C15—H150.54C20—C19—C24—C230.66 (9)
H6—O6—C14—C13173.99C20—C21—C22—C230.94 (9)
H6—O6—C14—C156.36C20—C21—C22—H22178.94
C7—N2—C11—C100.92 (8)C21—C20—C19—C240.94 (9)
C7—N2—C11—H11179.09C21—C22—C23—C241.22 (10)
C7—C8—C9—C101.50 (9)C21—C22—C23—H23178.89
C7—C8—C9—H9178.50H21—C21—C22—C23178.96
H7—C7—N2—C11178.91H21—C21—C22—H221.16
H7—C7—C8—C120.35H22—C22—C23—C24178.67
H7—C7—C8—C9179.86H22—C22—C23—H231.22
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i1.011.712.7137 (7)172
N2—H2···O2i1.012.483.1987 (9)127
N2—H2···C6i1.012.363.3145 (9)157
C5—H5···O8i1.082.563.1297 (8)112
C7—H7···O2i1.082.603.2628 (9)119
C7—H7···O10i1.082.373.3124 (8)145
O6—H6···O9ii0.982.002.9708 (8)169
C15—H15···O9ii1.082.593.3947 (8)131
N1—H1···O31.011.662.6696 (7)175
N1—H1···O41.012.533.2085 (9)124
N1—H1···C121.012.363.2963 (9)154
C1—H1A···O41.082.533.2175 (8)121
O5—H5A···O40.981.862.6851 (8)140
O5—H5A···O60.982.422.7908 (8)102
O7—H7A···O10.981.902.7045 (7)137
O8—H8···O100.982.262.6913 (7)105
C9—H9···O61.082.523.5056 (9)151
O9—H9A···O80.982.322.7593 (8)106
O10—H10A···O20.981.712.6349 (8)156
O8—H8···O3iii0.981.892.7498 (8)144
C11—H11···O2iv1.082.483.1465 (9)118
C5—H5···O4v1.082.323.0351 (9)122
C15—H15···O7vi1.082.623.4564 (9)134
C16—H16···O5vi1.082.463.2500 (8)129
O9—H9A···O7vii0.981.932.8143 (7)149
C21—H21···O10vii1.082.403.2758 (8)136
C17—H17···O8viii1.082.603.4596 (8)136
Symmetry codes: (i) x, y1, z; (ii) x, y1, z+1; (iii) x, y+1, z; (iv) x+3/2, y1, z+1/2; (v) x+3/2, y, z1/2; (vi) x+1, y+1, z+1/2; (vii) x+1, y+2, z1/2; (viii) x+1, y+2, z+1/2.
(multipolar_MoPro) top
Crystal data top
C6H5NO2·C6H6O3Dx = 1.566 Mg m3
Mr = 249.22Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21Cell parameters from 2780 reflections
a = 13.6648 (4) Åθ = 2.3–52.2°
b = 11.9321 (3) ŵ = 0.12 mm1
c = 12.9678 (4) ÅT = 100 K
V = 2114.40 (10) Å3Block, brown
Z = 80.35 × 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 scanRint = 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 = 0.750h = 3021
101259 measured reflectionsk = 2624
19169 independent reflectionsl = 2828
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034H-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 reflectionsΔρmax = 0.34 e Å3
1075 parametersΔρmin = 0.34 e Å3
0 restraintsAbsolute structure: Rogers (1981), 8469 Friedel pairs
Primary atom site location: structure-invariant direct methodsRogers 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
xyzUiso*/Ueq
O10.68090 (2)0.64338 (3)0.547620 (6)0.015210 (14)
N10.68875 (2)0.35065 (3)0.37576 (4)0.011509 (13)
H10.684200.271410.416200.02558
C10.68309 (3)0.44392 (3)0.43328 (4)0.010812 (14)
H1A0.669600.427020.514360.02649
O20.68742 (2)0.74541 (3)0.40319 (4)0.017211 (15)
N20.67965 (2)0.14701 (3)0.62887 (3)0.011375 (13)
H20.679240.225240.588050.02593
C20.68698 (2)0.54858 (3)0.38670 (4)0.010287 (14)
O30.68263 (2)0.14660 (3)0.46002 (3)0.015081 (14)
C30.69544 (3)0.55390 (3)0.27960 (4)0.012285 (15)
H30.700800.633570.239220.02621
O40.67786 (2)0.24881 (3)0.60438 (4)0.015723 (13)
C40.70135 (3)0.45585 (3)0.22178 (4)0.013279 (16)
H40.714760.458610.139340.02551
C50.69796 (3)0.35401 (3)0.27262 (4)0.012910 (16)
H50.704420.274930.232040.02345
O50.56144 (2)0.40676 (2)0.68628 (3)0.014828 (13)
H5A0.599140.335780.685160.02559
O60.58028 (2)0.28220 (2)0.86722 (4)0.016431 (13)
H60.574880.248940.936550.02326
C60.68411 (3)0.65407 (3)0.45043 (4)0.011740 (15)
C70.68004 (3)0.05256 (3)0.57242 (4)0.011191 (15)
H70.680710.068290.490020.02381
O70.54119 (2)0.63227 (2)0.69511 (3)0.013985 (12)
H7A0.580360.597320.639490.02620
O80.57053 (2)1.13634 (2)0.28401 (3)0.014451 (12)
H80.601161.101970.345590.02487
C80.67818 (2)0.05129 (3)0.62078 (4)0.010193 (14)
C90.67578 (3)0.05494 (3)0.72828 (4)0.012078 (15)
H90.671770.135230.768010.02486
O90.54931 (2)1.19663 (2)0.07989 (4)0.015353 (13)
H9A0.527511.243760.138120.02641
C100.67774 (3)0.04438 (3)0.78495 (4)0.012692 (15)
H100.677370.043560.868690.02400
O100.58562 (2)0.91928 (2)0.33847 (3)0.014056 (13)
H10A0.613840.843870.353240.02639
C110.67919 (3)0.14549 (3)0.73257 (4)0.012351 (15)
H110.681150.226690.770220.02658
C120.67898 (3)0.15756 (3)0.55730 (4)0.011442 (15)
C130.56219 (2)0.45555 (3)0.78113 (4)0.010470 (13)
C140.57028 (2)0.39612 (3)0.87400 (4)0.011408 (14)
C150.56856 (3)0.45315 (3)0.96799 (4)0.013364 (16)
H150.577340.402781.037270.02636
C160.55731 (3)0.56930 (3)0.97008 (4)0.014164 (16)
H160.553660.612711.043690.02659
C170.54835 (3)0.62915 (3)0.87837 (4)0.012971 (15)
H170.530550.717860.874390.02712
C180.55113 (2)0.57221 (3)0.78479 (4)0.010619 (13)
C190.56858 (2)1.05468 (3)0.21025 (4)0.010177 (14)
C200.55765 (2)1.08586 (3)0.10726 (4)0.011211 (14)
C210.55605 (3)1.00476 (3)0.02999 (4)0.014420 (17)
H210.540601.032860.048100.02647
C220.56525 (3)0.89216 (4)0.05637 (4)0.016084 (17)
H220.561000.828640.003600.02600
C230.57464 (3)0.85922 (3)0.15933 (4)0.013821 (16)
H230.582650.772470.184010.02656
C240.57651 (3)0.94088 (3)0.23599 (4)0.010626 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.02419 (13)0.01087 (11)0.01058 (11)0.00067 (9)0.00410 (9)0.00163 (8)
N10.01425 (10)0.00881 (11)0.01146 (11)0.00052 (8)0.00022 (9)0.00081 (9)
H10.038950.017010.020770.000080.001270.00250
C10.01457 (12)0.00884 (12)0.00903 (11)0.00000 (9)0.00024 (9)0.00014 (9)
H1A0.039800.024920.014730.000400.002130.00041
O20.02650 (13)0.00853 (10)0.01661 (13)0.00223 (9)0.00198 (10)0.00208 (9)
N20.01487 (11)0.00893 (11)0.01032 (11)0.00079 (9)0.00019 (9)0.00004 (9)
H20.038770.017140.021870.000730.000550.00296
C20.01306 (11)0.00854 (11)0.00926 (12)0.00066 (9)0.00060 (9)0.00024 (9)
O30.02558 (13)0.01055 (11)0.00911 (10)0.00177 (9)0.00177 (9)0.00041 (8)
C30.01592 (12)0.01146 (13)0.00948 (12)0.00022 (9)0.00051 (10)0.00114 (11)
H30.039080.017260.022290.000490.000650.00380
O40.02531 (13)0.00856 (10)0.01329 (11)0.00050 (9)0.00021 (10)0.00215 (9)
C40.01663 (13)0.01420 (14)0.00900 (12)0.00131 (10)0.00125 (10)0.00125 (10)
H40.036770.025220.014550.000460.001260.00000
C50.01509 (12)0.01172 (13)0.01192 (14)0.00118 (10)0.00166 (10)0.00292 (10)
H50.030250.018990.021100.004940.000720.00064
O50.02301 (12)0.01218 (10)0.00930 (10)0.00285 (9)0.00268 (9)0.00170 (8)
H5A0.036990.017900.021870.000930.000870.00484
O60.02442 (12)0.01080 (10)0.01407 (11)0.00029 (9)0.00089 (10)0.00227 (9)
H60.031710.021530.016540.000300.001230.00207
C60.01570 (12)0.00855 (12)0.01097 (12)0.00095 (10)0.00196 (10)0.00022 (10)
C70.01545 (13)0.00932 (12)0.00880 (11)0.00008 (10)0.00036 (10)0.00090 (9)
H70.030500.022590.018340.004740.003700.00120
O70.02046 (11)0.01166 (10)0.00984 (10)0.00334 (9)0.00276 (9)0.00183 (8)
H7A0.038270.024920.015420.000220.000070.00079
O80.02360 (11)0.00921 (9)0.01054 (9)0.00039 (8)0.00356 (10)0.00151 (8)
H80.034400.021450.018740.004120.004330.00058
C80.01337 (12)0.00879 (12)0.00842 (11)0.00035 (9)0.00048 (9)0.00025 (9)
C90.01624 (13)0.01110 (12)0.00889 (12)0.00016 (10)0.00012 (10)0.00092 (10)
H90.035230.020410.018950.003520.002060.00199
O90.02226 (12)0.01255 (11)0.01125 (10)0.00244 (9)0.00034 (9)0.00280 (8)
H9A0.039030.017560.022630.000320.000760.00407
C100.01621 (13)0.01338 (13)0.00849 (11)0.00053 (10)0.00059 (11)0.00066 (11)
H100.033390.017740.020850.005060.000270.00034
O100.02160 (11)0.01085 (10)0.00972 (10)0.00193 (9)0.00043 (9)0.00120 (8)
H10A0.038450.025380.015350.000710.000090.00011
C110.01498 (12)0.01117 (13)0.01090 (13)0.00111 (10)0.00040 (10)0.00185 (10)
H110.038620.017880.023240.000890.000430.00466
C120.01627 (12)0.00863 (12)0.00943 (12)0.00071 (10)0.00124 (10)0.00051 (9)
C130.01329 (11)0.00987 (11)0.00825 (10)0.00019 (9)0.00089 (9)0.00007 (10)
C140.01361 (11)0.01111 (12)0.00950 (11)0.00042 (9)0.00055 (10)0.00130 (10)
C150.01608 (13)0.01538 (14)0.00863 (11)0.00056 (11)0.00007 (10)0.00106 (10)
H150.037690.024080.017310.001640.000690.00415
C160.01809 (13)0.01565 (14)0.00876 (11)0.00005 (11)0.00133 (11)0.00138 (10)
H160.038360.024480.016930.001920.000200.00470
C170.01675 (13)0.01198 (13)0.01018 (12)0.00059 (10)0.00215 (11)0.00129 (10)
H170.040210.016600.024570.003380.000030.00083
C180.01325 (11)0.00990 (11)0.00871 (10)0.00060 (9)0.00111 (10)0.00007 (10)
C190.01269 (11)0.00938 (12)0.00846 (11)0.00008 (9)0.00089 (9)0.00032 (9)
C200.01304 (11)0.01185 (13)0.00874 (11)0.00127 (10)0.00071 (9)0.00047 (10)
C210.01743 (14)0.01667 (15)0.00916 (11)0.00397 (11)0.00129 (10)0.00194 (10)
H210.038130.025200.016080.002210.001740.00266
C220.02131 (15)0.01483 (14)0.01211 (13)0.00414 (12)0.00250 (12)0.00449 (11)
H220.037320.021020.019650.001790.000330.00504
C230.01756 (13)0.01077 (13)0.01313 (13)0.00189 (10)0.00117 (11)0.00288 (10)
H230.039350.016170.024150.002330.000570.00205
C240.01310 (11)0.00947 (12)0.00930 (11)0.00031 (9)0.00010 (9)0.00044 (9)
Geometric parameters (Å, º) top
O1—C61.2675 (5)C8—C121.5117 (5)
N1—C11.3420 (5)C8—C91.3952 (5)
N1—C51.3440 (5)C9—C101.3947 (5)
N1—H11.0829C9—H91.0892
C1—C21.3883 (5)O9—C201.3733 (5)
C1—H1A1.0863O9—H9A0.9874
O2—C61.2511 (5)C10—C111.3846 (5)
N2—C71.3439 (5)C10—H101.0860
N2—C111.3449 (5)O10—C241.3595 (5)
N2—H21.0731O10—H10A0.9975
C2—C61.5063 (5)C11—H111.0853
C2—C31.3951 (5)C13—C181.4009 (5)
O3—C121.2693 (5)C13—C141.4020 (5)
C3—C41.3920 (5)C14—C151.3961 (5)
C3—H31.0877C15—C161.3947 (6)
O4—C121.2484 (5)C15—H151.0875
C4—C51.3832 (6)C16—C171.3926 (6)
C4—H41.0852C16—H161.0872
C5—H51.0840C17—C181.3913 (5)
O5—C131.3609 (5)C17—H171.0873
O5—H5A0.9914C19—C201.3945 (5)
O6—C141.3690 (5)C19—C241.4025 (5)
O6—H60.9855C20—C211.3931 (5)
C7—C81.3890 (5)C21—C221.3921 (6)
C7—H71.0850C21—H211.0874
O7—C181.3728 (5)C22—C231.3976 (6)
O7—H7A0.9903C22—H221.0876
O8—C191.3657 (4)C23—C241.3921 (5)
O8—H80.9905C23—H231.0890
C1—N1—C5122.26 (3)N2—C11—C10120.16 (3)
C1—N1—H1116.84N2—C11—H11115.95
C5—N1—H1120.89C10—C11—H11123.88
N1—C1—C2120.13 (3)O4—C12—O3125.19 (3)
N1—C1—H1A113.20O4—C12—C8117.73 (3)
C2—C1—H1A126.48O3—C12—C8117.07 (3)
C7—N2—C11122.23 (3)O5—C13—C18117.06 (3)
C7—N2—H2117.43O5—C13—C14124.10 (3)
C11—N2—H2120.33C18—C13—C14118.81 (3)
C6—C2—C1120.80 (3)O6—C14—C13117.06 (3)
C6—C2—C3120.68 (3)O6—C14—C15122.80 (3)
C1—C2—C3118.51 (3)C13—C14—C15120.14 (3)
C2—C3—C4120.18 (3)C14—C15—C16120.21 (3)
C2—C3—H3121.64C14—C15—H15116.74
C4—C3—H3118.12C16—C15—H15123.05
C5—C4—C3118.67 (3)C17—C16—C15120.18 (3)
C5—C4—H4120.12C17—C16—H16120.09
C3—C4—H4120.99C15—C16—H16119.71
N1—C5—C4120.24 (3)C18—C17—C16119.47 (3)
N1—C5—H5117.69C18—C17—H17116.11
C4—C5—H5122.05C16—C17—H17124.02
C13—O5—H5A112.01O7—C18—C13120.04 (3)
C14—O6—H6109.50O7—C18—C17118.77 (3)
O2—C6—O1125.16 (3)C13—C18—C17121.18 (3)
O2—C6—C2117.28 (3)O8—C19—C20118.85 (3)
O1—C6—C2117.54 (3)O8—C19—C24121.51 (3)
N2—C7—C8120.14 (3)C20—C19—C24119.64 (3)
N2—C7—H7113.04O9—C20—C19120.87 (3)
C8—C7—H7126.81O9—C20—C21118.78 (3)
C18—O7—H7A110.11C19—C20—C21120.35 (3)
C19—O8—H8106.11C20—C21—C22119.48 (3)
C12—C8—C7120.15 (3)C20—C21—H21117.30
C12—C8—C9121.20 (3)C22—C21—H21122.96
C7—C8—C9118.64 (3)C21—C22—C23120.96 (3)
C8—C9—C10119.97 (3)C21—C22—H22119.47
C8—C9—H9120.08C23—C22—H22119.48
C10—C9—H9119.94C24—C23—C22119.14 (3)
C20—O9—H9A112.05C24—C23—H23116.97
C11—C10—C9118.82 (3)C22—C23—H23123.87
C11—C10—H10119.90O10—C24—C19115.04 (3)
C9—C10—H10121.27O10—C24—C23124.55 (3)
C24—O10—H10A113.21C19—C24—C23120.41 (3)
O1—C6—C2—C11.99 (5)O7—C18—C13—C14178.78 (4)
O1—C6—C2—C3176.82 (5)O7—C18—C17—C16179.34 (4)
N1—C1—C2—C6177.94 (5)O7—C18—C17—H176.29
N1—C1—C2—C30.88 (5)H7A—O7—C18—C1334.06
N1—C5—C4—C30.25 (5)H7A—O7—C18—C17146.99
N1—C5—C4—H4174.97O8—C19—C20—O90.24 (5)
H1—N1—C1—C2179.09O8—C19—C20—C21179.55 (5)
H1—N1—C1—H1A3.84O8—C19—C24—O100.30 (4)
H1—N1—C5—C4178.46O8—C19—C24—C23179.79 (5)
H1—N1—C5—H53.10H8—O8—C19—C20160.67
C1—N1—C5—C40.38 (5)H8—O8—C19—C2419.86
C1—N1—C5—H5178.06C8—C7—N2—C111.17 (5)
C1—C2—C6—O2179.65 (5)C8—C9—C10—C111.87 (5)
C1—C2—C3—C41.00 (5)C8—C9—C10—H10178.79
C1—C2—C3—H3178.31C9—C10—C11—H11179.65
H1A—C1—N1—C5175.05H9—C9—C8—C122.22
H1A—C1—C2—C67.49H9—C9—C10—C11177.63
H1A—C1—C2—C3173.68H9—C9—C10—H101.71
O2—C6—C2—C31.55 (5)O9—C20—C19—C24179.73 (5)
N2—C7—C8—C12179.79 (5)O9—C20—C21—C22179.46 (5)
N2—C7—C8—C90.09 (5)O9—C20—C21—H216.22
N2—C11—C10—C90.65 (5)H9A—O9—C20—C1921.35
N2—C11—C10—H10180.00H9A—O9—C20—C21159.33
H2—N2—C7—C8178.44C10—C9—C8—C12178.28 (5)
H2—N2—C7—H70.64H10—C10—C11—H111.00
H2—N2—C11—C10178.71O10—C24—C19—C20179.17 (4)
H2—N2—C11—H112.21O10—C24—C23—C22179.79 (5)
C2—C1—N1—C50.20 (5)O10—C24—C23—H231.35
C2—C3—C4—C50.45 (5)H10A—O10—C24—C19159.93
C2—C3—C4—H4174.22H10A—O10—C24—C2320.17
O3—C12—C8—C70.87 (5)C13—C18—C17—C160.40 (5)
O3—C12—C8—C9179.00 (5)C13—C18—C17—H17172.65
C3—C4—C5—H5178.12C13—C14—C15—C160.96 (5)
H3—C3—C2—C60.52C13—C14—C15—H15178.22
H3—C3—C4—C5177.84C14—C13—C18—C170.15 (5)
H3—C3—C4—H43.18C14—C15—C16—C170.41 (5)
O4—C12—C8—C7179.55 (5)C14—C15—C16—H16178.01
O4—C12—C8—C90.32 (5)C15—C14—C13—C180.83 (5)
C4—C3—C2—C6177.83 (5)C15—C16—C17—C180.27 (5)
H4—C4—C5—H53.40C15—C16—C17—H17172.20
O5—C13—C18—O70.67 (4)H15—C15—C16—C17178.72
O5—C13—C18—C17178.26 (5)H15—C15—C16—H162.86
O5—C13—C14—O61.57 (4)H16—C16—C17—C18178.68
O5—C13—C14—C15178.80 (5)H16—C16—C17—H176.21
H5A—O5—C13—C18152.88C19—C20—C21—C220.14 (5)
H5A—O5—C13—C1429.12C19—C20—C21—H21174.46
O6—C14—C13—C18179.54 (5)C19—C24—C23—C220.31 (5)
O6—C14—C15—C16179.43 (5)C19—C24—C23—H23178.75
O6—C14—C15—H151.39C20—C19—C24—C230.74 (5)
H6—O6—C14—C13171.20C20—C21—C22—C230.94 (5)
H6—O6—C14—C159.18C20—C21—C22—H22177.49
C7—N2—C11—C100.88 (5)C21—C20—C19—C240.96 (5)
C7—N2—C11—H11178.19C21—C22—C23—C241.16 (6)
C7—C8—C9—C101.59 (5)C21—C22—C23—H23179.48
C7—C8—C9—H9177.90H21—C21—C22—C23173.05
H7—C7—N2—C11179.75H21—C21—C22—H223.51
H7—C7—C8—C121.27H22—C22—C23—C24177.71
H7—C7—C8—C9178.85H22—C22—C23—H233.97
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i1.071.652.7140 (4)169 (1)
N2—H2···O2i1.072.423.1975 (5)128 (1)
N2—H2···C6i1.072.293.3153 (5)158 (1)
C5—H5···O8i1.082.563.1304 (5)112
C7—H7···O2i1.092.493.2615 (5)126
C7—H7···O10i1.092.363.3138 (5)145
O6—H6···O9ii0.991.992.9711 (5)172 (1)
C15—H15···O9ii1.092.553.3975 (5)134
N1—H1···O31.081.592.6700 (4)172 (1)
N1—H1···O41.082.463.2075 (5)125 (1)
N1—H1···C121.082.283.2968 (5)156 (1)
C1—H1A···O41.092.433.2168 (5)128
O5—H5A···O40.991.832.6853 (4)143 (1)
O7—H7A···O10.991.902.7056 (4)137 (1)
O8—H8···O100.992.192.6925 (4)110 (1)
C9—H9···O61.092.513.5076 (5)151
O9—H9A···O80.992.362.7582 (4)103 (1)
O10—H10A···O21.001.682.6350 (4)160 (1)
O8—H8···O3iii0.991.932.7515 (4)138
C11—H11···O2iv1.092.513.1485 (5)116
C5—H5···O4v1.082.333.0356 (5)121
C16—H16···O5vi1.092.443.2519 (5)130
O9—H9A···O7vii0.991.902.8160 (4)153 (1)
C21—H21···O10vii1.092.343.2767 (5)143
C17—H17···O8viii1.092.513.4592 (5)145
Symmetry codes: (i) x, y1, z; (ii) x, y1, z+1; (iii) x, y+1, z; (iv) x+3/2, y1, z+1/2; (v) x+3/2, y, z1/2; (vi) x+1, y+1, z+1/2; (vii) x+1, y+2, z1/2; (viii) x+1, y+2, z+1/2.
(IAM_SHELX) top
Crystal data top
C6H5NO2·C6H6O3Dx = 1.566 Mg m3
Mr = 249.22Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21Cell parameters from 2780 reflections
a = 13.6648 (4) Åθ = 2.3–52.2°
b = 11.9321 (3) ŵ = 0.12 mm1
c = 12.9678 (4) ÅT = 100 K
V = 2114.40 (10) Å3Block, brown
Z = 80.35 × 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 scanRint = 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 = 0.750h = 3021
101259 measured reflectionsk = 2624
23980 independent reflectionsl = 2828
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH 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 = 1.04Δρmax = 0.60 e Å3
23980 reflectionsΔρmin = 0.29 e Å3
337 parametersAbsolute structure: Flack x determined using 7550 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
1 restraintAbsolute 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
xyzUiso*/Ueq
O10.68082 (5)0.64347 (5)0.54764 (5)0.01535 (10)
N10.68877 (5)0.35064 (5)0.37566 (6)0.01162 (8)
H10.6863550.2850330.4065640.014*
C10.68307 (5)0.44402 (6)0.43316 (6)0.01072 (9)
H1A0.6763240.4384330.5058890.013*
O20.68742 (5)0.74545 (5)0.40301 (6)0.01741 (11)
N20.67966 (5)0.14702 (5)0.62883 (5)0.01139 (8)
H20.6797900.2120870.5968910.014*
C20.68700 (5)0.54851 (5)0.38668 (5)0.01018 (9)
O30.68259 (5)0.14651 (5)0.45988 (5)0.01530 (9)
C30.69544 (5)0.55387 (6)0.27962 (6)0.01225 (9)
H30.6971580.6246230.2460690.015*
O40.67779 (5)0.24879 (5)0.60445 (5)0.01592 (9)
C40.70134 (6)0.45578 (6)0.22175 (6)0.01330 (10)
H40.7075180.4587120.1488350.016*
C50.69803 (5)0.35398 (6)0.27269 (6)0.01294 (10)
H5A0.7023360.2861430.2346080.016*
O50.56137 (5)0.40691 (5)0.68616 (5)0.01506 (9)
H50.5908 (13)0.3478 (16)0.6884 (3)0.023*
O60.58033 (5)0.28210 (5)0.86705 (5)0.01673 (10)
H60.5771 (13)0.2562 (8)0.9213 (16)0.025*
C60.68414 (5)0.65411 (6)0.45048 (6)0.01154 (9)
C70.67999 (5)0.05258 (6)0.57240 (6)0.01108 (9)
H7A0.6814750.0568490.4992660.013*
O70.54108 (5)0.63227 (5)0.69503 (5)0.01410 (9)
H70.5731 (12)0.6035 (12)0.6504 (12)0.021*
O80.57046 (5)1.13643 (5)0.28395 (5)0.01470 (9)
H80.5982 (12)1.1132 (8)0.3349 (14)0.022*
C80.67815 (5)0.05133 (6)0.62076 (5)0.01010 (9)
C90.67580 (5)0.05490 (6)0.72827 (6)0.01197 (9)
H9A0.6729340.1249880.7628860.014*
O90.54934 (5)1.19671 (5)0.07977 (5)0.01553 (9)
H90.5312 (13)1.2341 (10)0.1306 (13)0.023*
C100.67766 (5)0.04442 (6)0.78492 (6)0.01265 (10)
H10A0.6778950.0427700.8581630.015*
O100.58561 (5)0.91940 (5)0.33843 (5)0.01431 (9)
H100.6080 (13)0.8565 (15)0.34655 (19)0.021*
C110.67915 (5)0.14535 (6)0.73254 (6)0.01221 (10)
H110.6798230.2138000.7699560.015*
C120.67897 (5)0.15765 (6)0.55722 (6)0.01125 (9)
C130.56221 (5)0.45548 (5)0.78113 (6)0.01051 (8)
C140.57028 (5)0.39613 (6)0.87398 (6)0.01125 (9)
C150.56847 (6)0.45310 (7)0.96798 (6)0.01328 (10)
H150.5749190.4126301.0307030.016*
C160.55723 (6)0.56921 (7)0.97011 (6)0.01410 (10)
H160.5556710.6076001.0342740.017*
C170.54828 (6)0.62910 (6)0.87831 (6)0.01287 (9)
H170.5403130.7081770.8796370.015*
C180.55110 (5)0.57222 (6)0.78476 (6)0.01052 (8)
C190.56865 (5)1.05461 (6)0.21035 (5)0.01024 (9)
C200.55768 (5)1.08585 (6)0.10737 (6)0.01107 (9)
C210.55606 (6)1.00465 (7)0.02986 (6)0.01446 (11)
H210.5487361.0260000.0402890.017*
C220.56529 (6)0.89208 (7)0.05642 (7)0.01591 (11)
H220.5652180.8367710.0037230.019*
C230.57464 (6)0.85923 (6)0.15926 (6)0.01364 (10)
H230.5796610.7821240.1767340.016*
C240.57650 (5)0.94088 (6)0.23589 (5)0.01050 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0241 (3)0.01132 (19)0.0106 (2)0.00069 (17)0.00425 (17)0.00178 (15)
N10.0142 (2)0.00903 (18)0.0116 (2)0.00026 (15)0.00022 (16)0.00081 (16)
C10.0141 (2)0.0088 (2)0.0093 (2)0.00005 (17)0.00028 (17)0.00001 (16)
O20.0268 (3)0.00857 (18)0.0169 (2)0.00219 (18)0.0020 (2)0.00232 (17)
N20.0147 (2)0.00907 (19)0.0104 (2)0.00089 (15)0.00014 (16)0.00003 (15)
C20.0127 (2)0.0088 (2)0.0090 (2)0.00076 (16)0.00055 (16)0.00022 (15)
O30.0262 (3)0.01100 (19)0.00868 (19)0.00197 (17)0.00171 (17)0.00046 (14)
C30.0155 (2)0.0115 (2)0.0098 (2)0.00032 (17)0.00033 (19)0.00107 (18)
O40.0254 (3)0.00895 (18)0.0134 (2)0.00066 (17)0.00003 (18)0.00244 (16)
C40.0160 (2)0.0149 (3)0.0090 (2)0.0014 (2)0.00129 (19)0.00155 (18)
C50.0146 (2)0.0123 (2)0.0119 (2)0.00104 (18)0.00137 (19)0.00284 (18)
O50.0235 (2)0.01238 (19)0.00926 (18)0.00303 (17)0.00269 (16)0.00188 (15)
O60.0257 (3)0.01043 (18)0.0140 (2)0.00018 (17)0.00106 (19)0.00247 (16)
C60.0147 (2)0.0087 (2)0.0112 (2)0.00105 (17)0.00180 (18)0.00041 (16)
C70.0149 (2)0.0095 (2)0.0088 (2)0.00018 (17)0.00033 (17)0.00063 (16)
O70.0211 (2)0.01177 (18)0.00942 (18)0.00354 (17)0.00307 (16)0.00203 (14)
O80.0246 (2)0.00936 (17)0.01017 (18)0.00046 (16)0.00411 (18)0.00161 (15)
C80.0129 (2)0.0090 (2)0.0084 (2)0.00027 (16)0.00043 (16)0.00028 (15)
C90.0154 (2)0.0113 (2)0.0091 (2)0.00031 (18)0.00018 (17)0.00114 (17)
O90.0231 (2)0.01198 (19)0.01149 (19)0.00270 (18)0.00054 (17)0.00284 (16)
C100.0156 (2)0.0134 (2)0.0089 (2)0.00050 (18)0.00061 (19)0.00089 (18)
O100.0222 (2)0.01103 (18)0.00970 (18)0.00224 (17)0.00031 (16)0.00134 (14)
C110.0143 (2)0.0114 (2)0.0110 (2)0.00107 (18)0.00054 (18)0.00195 (17)
C120.0154 (2)0.0088 (2)0.0095 (2)0.00066 (17)0.00140 (18)0.00056 (16)
C130.0126 (2)0.0105 (2)0.00843 (19)0.00008 (16)0.00084 (17)0.00004 (17)
C140.0131 (2)0.0110 (2)0.0096 (2)0.00061 (16)0.00037 (17)0.00152 (18)
C150.0157 (2)0.0156 (3)0.0085 (2)0.0008 (2)0.00000 (18)0.00107 (19)
C160.0172 (3)0.0162 (3)0.0090 (2)0.0001 (2)0.00149 (19)0.00142 (19)
C170.0162 (2)0.0120 (2)0.0104 (2)0.00054 (18)0.00199 (19)0.00148 (18)
C180.0127 (2)0.0103 (2)0.00860 (18)0.00042 (16)0.00097 (17)0.00027 (17)
C190.0125 (2)0.0095 (2)0.0087 (2)0.00006 (16)0.00072 (16)0.00031 (15)
C200.0126 (2)0.0116 (2)0.0089 (2)0.00133 (17)0.00060 (16)0.00054 (17)
C210.0174 (3)0.0169 (3)0.0091 (2)0.0040 (2)0.00108 (19)0.00193 (19)
C220.0202 (3)0.0153 (3)0.0122 (2)0.0041 (2)0.0023 (2)0.0045 (2)
C230.0173 (3)0.0107 (2)0.0130 (2)0.00187 (19)0.0010 (2)0.00283 (18)
C240.0127 (2)0.0094 (2)0.0094 (2)0.00024 (17)0.00003 (16)0.00045 (16)
Geometric parameters (Å, º) top
O1—C61.2672 (10)C8—C91.3951 (10)
N1—H10.8800C8—C121.5128 (10)
N1—C11.3429 (9)C9—H9A0.9500
N1—C51.3419 (10)C9—C101.3945 (10)
C1—H1A0.9500O9—H90.83 (2)
C1—C21.3859 (9)O9—C201.3751 (9)
O2—C61.2525 (10)C10—H10A0.9500
N2—H20.8800C10—C111.3829 (11)
N2—C71.3436 (9)O10—H100.818 (18)
N2—C111.3450 (10)O10—C241.3599 (9)
C2—C31.3946 (10)C11—H110.9500
C2—C61.5079 (10)C13—C141.4012 (10)
O3—C121.2703 (9)C13—C181.4020 (9)
C3—H30.9500C14—C151.3960 (10)
C3—C41.3926 (10)C15—H150.9500
O4—C121.2481 (9)C15—C161.3942 (11)
C4—H40.9500C16—H160.9500
C4—C51.3835 (11)C16—C171.3938 (11)
C5—H5A0.9500C17—H170.9500
O5—H50.812 (18)C17—C181.3906 (10)
O5—C131.3611 (9)C19—C201.3945 (10)
O6—H60.77 (2)C19—C241.4010 (9)
O6—C141.3704 (9)C20—C211.3962 (10)
C7—H7A0.9500C21—H210.9500
C7—C81.3897 (10)C21—C221.3924 (12)
O7—H70.80 (2)C22—H220.9500
O7—C181.3733 (9)C22—C231.3960 (12)
O8—H80.81 (2)C23—H230.9500
O8—C191.3655 (9)C23—C241.3918 (10)
C1—N1—H1118.9N2—C11—C10120.27 (7)
C5—N1—H1118.9N2—C11—H11119.9
C5—N1—C1122.23 (6)C10—C11—H11119.9
N1—C1—H1A119.9O3—C12—C8116.99 (6)
N1—C1—C2120.18 (7)O4—C12—O3125.40 (7)
C2—C1—H1A119.9O4—C12—C8117.60 (7)
C7—N2—H2118.9O5—C13—C14124.26 (6)
C7—N2—C11122.16 (7)O5—C13—C18116.90 (6)
C11—N2—H2118.9C14—C13—C18118.80 (6)
C1—C2—C3118.52 (6)O6—C14—C13116.96 (6)
C1—C2—C6120.81 (6)O6—C14—C15122.85 (7)
C3—C2—C6120.66 (6)C15—C14—C13120.19 (6)
C2—C3—H3119.9C14—C15—H15119.9
C4—C3—C2120.17 (6)C16—C15—C14120.21 (7)
C4—C3—H3119.9C16—C15—H15119.9
C3—C4—H4120.7C15—C16—H16119.9
C5—C4—C3118.61 (7)C17—C16—C15120.14 (7)
C5—C4—H4120.7C17—C16—H16119.9
N1—C5—C4120.29 (7)C16—C17—H17120.2
N1—C5—H5A119.9C18—C17—C16119.50 (7)
C4—C5—H5A119.9C18—C17—H17120.2
C13—O5—H5109.5O7—C18—C13120.05 (6)
C14—O6—H6109.5O7—C18—C17118.80 (6)
O1—C6—C2117.56 (6)C17—C18—C13121.15 (6)
O2—C6—O1125.25 (7)O8—C19—C20118.70 (6)
O2—C6—C2117.17 (7)O8—C19—C24121.73 (6)
N2—C7—H7A119.9C20—C19—C24119.57 (6)
N2—C7—C8120.16 (7)O9—C20—C19121.02 (6)
C8—C7—H7A119.9O9—C20—C21118.61 (7)
C18—O7—H7109.5C19—C20—C21120.37 (7)
C19—O8—H8109.5C20—C21—H21120.3
C7—C8—C9118.59 (6)C22—C21—C20119.34 (7)
C7—C8—C12120.15 (6)C22—C21—H21120.3
C9—C8—C12121.26 (6)C21—C22—H22119.5
C8—C9—H9A120.0C21—C22—C23121.03 (7)
C10—C9—C8120.00 (7)C23—C22—H22119.5
C10—C9—H9A120.0C22—C23—H23120.4
C20—O9—H9109.5C24—C23—C22119.15 (7)
C9—C10—H10A120.6C24—C23—H23120.4
C11—C10—C9118.79 (7)O10—C24—C19114.88 (6)
C11—C10—H10A120.6O10—C24—C23124.59 (7)
C24—O10—H10109.5C23—C24—C19120.53 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O30.881.792.6706 (9)175
N1—H1···O40.882.603.2095 (10)126
C1—H1A···O40.952.603.2196 (10)123
N2—H2···O1i0.881.842.7127 (9)172
N2—H2···O2i0.882.573.1989 (10)129
C5—H5A···O4ii0.952.393.0356 (10)124
C5—H5A···O8i0.952.623.1303 (9)114
O5—H5···O40.812.002.6859 (9)142
O6—H6···O9iii0.772.212.9710 (9)171
C7—H7A···O10i0.952.483.3137 (10)146
O7—H7···O10.802.042.7050 (9)139
O8—H8···O3iv0.812.032.7508 (9)148
O9—H9···O7v0.832.052.8152 (9)151
O10—H10···O20.821.862.6353 (9)157
C11—H11···O2vi0.952.553.1478 (10)121
C21—H21···O10v0.952.503.2760 (10)138
Symmetry codes: (i) x, y1, z; (ii) x+3/2, y, z1/2; (iii) x, y1, z+1; (iv) x, y+1, z; (v) x+1, y+2, z1/2; (vi) x+3/2, y1, z+1/2.
(theoretical) top
Crystal data top
C24H22N2O10c = 12.9678 (4) Å
Mr = 498.42V = 2114.40 (10) Å3
Orthorhombic, Pca21Z = 4
Hall symbol: P ?F(000) = 1040
a = 13.6648 (4) ÅDx = 1.566 Mg m3
b = 11.9321 (3) ÅMo Kα radiation, λ = 0.71073 Å
Data collection top
Radiation source: fine-focus sealed tubeh = 030
24319 independent reflectionsk = 026
24319 reflections with > 2.0σ(I)l = 2828
θmax = 52.2°, θmin = 1.7°
Refinement top
Refinement on FSecondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.005H-atom parameters constrained
wR(F2) = 0.005Weighting scheme based on measured s.u.'s
S = 0.09(Δ/σ)max = 0.193
24319 reflectionsΔρmax = 0.15 e Å3
707 parametersΔρmin = 0.12 e Å3
0 restraintsAbsolute structure: Rogers (1981), 11836 Friedel pairs
Primary atom site location: structure-invariant direct methodsRogers 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
xyzUiso*/Ueq
O10.680890.643380.592160
N10.688790.350670.420220
H10.685420.269700.457670
C10.683100.443940.477770
H1A0.672640.431490.559940
O20.687510.745350.447750
N20.679680.146990.673410
H20.681420.225440.632920
C20.686990.548590.431240
O30.682620.146560.504460
C30.695450.553910.324070
H30.699610.634720.285400
O40.677930.248730.648860
C40.701370.455780.266280
H40.710050.460100.183090
C50.697960.354020.317140
H50.702760.274470.277000
O50.561420.406870.730840
H5A0.597700.334970.728080
O60.580310.282270.911770
H60.575670.254900.983220
C60.684130.654090.494920
C70.680040.052580.616930
H70.680280.063810.533810
O70.541180.632270.739620
H7A0.579650.598780.682620
O80.570461.136400.328540
H80.598021.105580.393160
C80.678250.051260.665290
C90.675760.054910.772760
H90.672910.136360.810480
O90.549341.196630.124360
H9A0.528121.242700.183450
C100.677750.044420.829490
H100.678400.042370.913120
O100.585590.919260.382920
H10A0.612850.842880.395140
C110.679170.145520.777050
H110.681150.227170.813770
C120.679000.157540.601790
C130.562190.455550.825610
C140.570200.396100.918520
C150.568540.453201.012470
H150.574170.405141.083390
C160.557330.569331.014580
H160.553630.610021.089410
C170.548360.629180.922870
H170.536910.719360.921070
C180.551100.572250.829290
C190.568571.054670.254730
C200.557701.085880.151790
C210.556081.004770.074520
H210.543821.030940.004840
C220.565240.892090.100870
H220.562260.827600.041600
C230.574630.859230.203850
H230.581240.770890.223720
C240.576520.940920.280450
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1000000
N1000000
H1000000
C1000000
H1A000000
O2000000
N2000000
H2000000
C2000000
O3000000
C3000000
H3000000
O4000000
C4000000
H4000000
C5000000
H5000000
O5000000
H5A000000
O6000000
H6000000
C6000000
C7000000
H7000000
O7000000
H7A000000
O8000000
H8000000
C8000000
C9000000
H9000000
O9000000
H9A000000
C10000000
H10000000
O10000000
H10A000000
C11000000
H11000000
C12000000
C13000000
C14000000
C15000000
H15000000
C16000000
H16000000
C17000000
H17000000
C18000000
C19000000
C20000000
C21000000
H21000000
C22000000
H22000000
C23000000
H23000000
C24000000
Geometric parameters (Å, º) top
O1—C61.2682C8—C121.5120
N1—C11.3421C8—C91.3948
N1—C51.3432C9—C101.3953
N1—H11.0824C9—H91.0887
C1—C21.3879O9—C201.3733
C1—H1A1.0854O9—H9A0.9866
O2—C61.2498C10—C111.3848
N2—C71.3436C10—H101.0848
N2—C111.3441O10—C241.3593
N2—H21.0736O10—H10A0.9973
C2—C61.5061C11—H111.0848
C2—C31.3960C13—C181.4015
O3—C121.2700C13—C141.4025
C3—C41.3926C14—C151.3960
C3—H31.0883C15—C161.3944
O4—C121.2478C15—H151.0866
C4—C51.3826C16—C171.3926
C4—H41.0865C16—H161.0862
C5—H51.0845C17—C181.3913
O5—C131.3594C17—H171.0876
O5—H5A0.9914C19—C201.3938
O6—C141.3681C19—C241.4020
O6—H60.9845C20—C211.3933
C7—C81.3890C21—C221.3928
C7—H71.0862C21—H211.0885
O7—C181.3724C22—C231.3977
O7—H7A0.9912C22—H221.0884
O8—C191.3666C23—C241.3920
O8—H80.9896C23—H231.0889
C1—N1—C5122.279N2—C11—C10120.159
C1—N1—H1119.229N2—C11—H11115.280
C5—N1—H1118.490C10—C11—H11124.553
N1—C1—C2120.140O4—C12—O3125.211
N1—C1—H1A116.106O4—C12—C8117.703
C2—C1—H1A123.709O3—C12—C8117.071
C7—N2—C11122.285O5—C13—C18117.040
C7—N2—H2117.668O5—C13—C14124.133
C11—N2—H2120.033C18—C13—C14118.795
C6—C2—C1120.840O6—C14—C13117.070
C6—C2—C3120.668O6—C14—C15122.822
C1—C2—C3118.482C13—C14—C15120.106
C2—C3—C4120.154C14—C15—C16120.260
C2—C3—H3120.219C14—C15—H15118.681
C4—C3—H3119.603C16—C15—H15121.039
C5—C4—C3118.668C17—C16—C15120.167
C5—C4—H4121.270C17—C16—H16121.976
C3—C4—H4120.049C15—C16—H16117.829
N1—C5—C4120.269C18—C17—C16119.480
N1—C5—H5117.213C18—C17—H17117.921
C4—C5—H5122.518C16—C17—H17122.571
C13—O5—H5A113.485O7—C18—C13120.017
C14—O6—H6105.222O7—C18—C17118.791
O2—C6—O1125.152C13—C18—C17121.184
O2—C6—C2117.313O8—C19—C20118.825
O1—C6—C2117.512O8—C19—C24121.519
N2—C7—C8120.115C20—C19—C24119.655
N2—C7—H7115.947O9—C20—C19120.932
C8—C7—H7123.926O9—C20—C21118.743
C18—O7—H7A111.661C19—C20—C21120.322
C19—O8—H8109.579C20—C21—C22119.517
C12—C8—C7120.145C20—C21—H21118.887
C12—C8—C9121.208C22—C21—H21121.517
C7—C8—C9118.646C21—C22—C23120.897
C8—C9—C10119.985C21—C22—H22120.389
C8—C9—H9118.533C23—C22—H22118.669
C10—C9—H9121.479C24—C23—C22119.147
C20—O9—H9A111.064C24—C23—H23120.493
C11—C10—C9118.775C22—C23—H23120.356
C11—C10—H10120.691O10—C24—C19115.066
C9—C10—H10120.533O10—C24—C23124.485
C24—O10—H10A111.293C19—C24—C23120.448
O1—C6—C2—C11.97O7—C18—C13—C14178.74
O1—C6—C2—C3176.83O7—C18—C17—C16179.36
N1—C1—C2—C6177.93O7—C18—C17—H171.23
N1—C1—C2—C30.90H7A—O7—C18—C1333.88
N1—C5—C4—C30.21H7A—O7—C18—C17147.10
N1—C5—C4—H4178.91O8—C19—C20—O90.23
H1—N1—C1—C2179.81O8—C19—C20—C21179.61
H1—N1—C1—H1A2.14O8—C19—C24—O100.30
H1—N1—C5—C4179.24O8—C19—C24—C23179.85
H1—N1—C5—H51.02H8—O8—C19—C20162.99
C1—N1—C5—C40.34H8—O8—C19—C2417.52
C1—N1—C5—H5179.40C8—C7—N2—C111.08
C1—C2—C6—O2179.71C8—C9—C10—C111.95
C1—C2—C3—C41.01C8—C9—C10—H10177.85
C1—C2—C3—H3179.22C9—C10—C11—H11179.65
H1A—C1—N1—C5177.43H9—C9—C8—C121.19
H1A—C1—C2—C64.59H9—C9—C10—C11178.59
H1A—C1—C2—C3176.58H9—C9—C10—H101.61
O2—C6—C2—C31.49O9—C20—C19—C24179.73
N2—C7—C8—C12179.79O9—C20—C21—C22179.49
N2—C7—C8—C90.20O9—C20—C21—H213.67
N2—C11—C10—C90.70H9A—O9—C20—C1920.77
N2—C11—C10—H10179.10H9A—O9—C20—C21159.85
H2—N2—C7—C8179.75C10—C9—C8—C12178.29
H2—N2—C7—H71.45H10—C10—C11—H110.14
H2—N2—C11—C10179.47O10—C24—C19—C20179.19
H2—N2—C11—H110.42O10—C24—C23—C22179.82
C2—C1—N1—C50.23O10—C24—C23—H230.53
C2—C3—C4—C50.47H10A—O10—C24—C19160.94
C2—C3—C4—H4178.25H10A—O10—C24—C2319.21
O3—C12—C8—C70.90C13—C18—C17—C160.35
O3—C12—C8—C9179.09C13—C18—C17—H17177.78
C3—C4—C5—H5179.50C13—C14—C15—C161.04
H3—C3—C2—C60.39C13—C14—C15—H15179.43
H3—C3—C4—C5178.69C14—C13—C18—C170.26
H3—C3—C4—H40.03C14—C15—C16—C170.42
O4—C12—C8—C7179.57C14—C15—C16—H16177.70
O4—C12—C8—C90.43C15—C14—C13—C180.95
C4—C3—C2—C6177.82C15—C16—C17—C180.28
H4—C4—C5—H50.81C15—C16—C17—H17177.77
O5—C13—C18—O70.72H15—C15—C16—C17178.76
O5—C13—C18—C17178.28H15—C15—C16—H160.65
O5—C13—C14—O61.73H16—C16—C17—C18178.31
O5—C13—C14—C15178.82H16—C16—C17—H170.27
H5A—O5—C13—C18153.93C19—C20—C21—C220.11
H5A—O5—C13—C1428.17C19—C20—C21—H21176.95
O6—C14—C13—C18179.60C19—C24—C23—C220.34
O6—C14—C15—C16179.54C19—C24—C23—H23179.63
O6—C14—C15—H151.16C20—C19—C24—C230.67
H6—O6—C14—C13172.49C20—C21—C22—C230.92
H6—O6—C14—C158.08C20—C21—C22—H22178.44
C7—N2—C11—C100.83C21—C20—C19—C240.90
C7—N2—C11—H11178.22C21—C22—C23—C241.15
C7—C8—C9—C101.70C21—C22—C23—H23179.57
C7—C8—C9—H9178.82H21—C21—C22—C23175.83
H7—C7—N2—C11179.88H21—C21—C22—H221.68
H7—C7—C8—C121.51H22—C22—C23—C24178.70
H7—C7—C8—C9178.49H22—C22—C23—H232.01
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i1.071.652.7142169
N2—H2···O2i1.072.433.1977128
N2—H2···C6i1.072.303.3158158
C5—H5···O8i1.092.543.1305114
C7—H7···O2i1.092.543.2615123
C7—H7···O10i1.092.363.3148147
O6—H6···O9ii0.981.992.9704173
C15—H15···O9ii1.092.573.3980133
N1—H1···O31.081.592.6705176
N1—H1···O41.082.493.2082123
N1—H1···C121.082.303.2974152
C1—H1A···O41.092.473.2177125
O5—H5A···O40.991.822.6880144
O7—H7A···O10.991.892.7054138
O8—H8···O100.992.232.6931107
C9—H9···O61.092.523.5085150
O9—H9A···O80.992.342.7587105
O10—H10A···O21.001.692.6368157
O8—H8···O3iii0.991.912.7510141
C11—H11···O2iv1.092.523.1487116
C5—H5···O4v1.092.353.0359120
C15—H15···O7vi1.092.613.4590135
C16—H16···O5vi1.092.423.2525132
O9—H9A···O7vii0.991.912.8164151
C21—H21···O10vii1.092.373.2776140
C17—H17···O8viii1.092.563.4578139
Symmetry codes: (i) x, y1, z; (ii) x, y1, z+1; (iii) x, y+1, z; (iv) x+3/2, y1, z+1/2; (v) x+3/2, y, z1/2; (vi) x+1, y+1, z+1/2; (vii) x+1, y+2, z1/2; (viii) x+1, y+2, z+1/2.
 

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