Crystals of the title compound, C
14H
10INO
2, whose asymmetric unit contains three independent molecules, are stabilized by three N—H
O, three C—H
O and one N—H
I intermolecular hydrogen bonds. In the structure, the N—H
O and C—H
O hydrogen bond interactions generate an edge-fused
R22(11) ring motif which appears as a molecular ladder in the structure.
Supporting information
CCDC reference: 633589
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.016 Å
- R factor = 0.063
- wR factor = 0.245
- Data-to-parameter ratio = 18.3
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 36 Perc.
Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.66 mm
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.12
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C24
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C23
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C26
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C30
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C40
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.09
PLAT334_ALERT_2_C Small Average Benzene C-C Dist. C37 -C42 1.35 Ang.
PLAT335_ALERT_2_C Large Benzene C-C Range ....... C23 -C28 0.16 Ang.
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 16
PLAT420_ALERT_2_C D-H Without Acceptor N3 - H3A ... ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3A .. O4 .. 2.61 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3A .. I1 .. 3.26 Ang.
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
14 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
10 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
3-(4-Iodoanilino)isobenzofuran-1(3
H)-one
top
Crystal data top
C14H10INO2 | F(000) = 2040 |
Mr = 351.13 | Dx = 1.801 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 36043 reflections |
a = 24.017 (3) Å | θ = 1.8–26.0° |
b = 6.9536 (6) Å | µ = 2.47 mm−1 |
c = 26.924 (5) Å | T = 296 K |
β = 120.207 (11)° | Plate, pale yellow |
V = 3885.9 (10) Å3 | 0.66 × 0.41 × 0.14 mm |
Z = 12 | |
Data collection top
Stoe IPDS-2 diffractometer | 7599 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 2725 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.075 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 1.5° |
ω scans | h = −29→29 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −8→8 |
Tmin = 0.285, Tmax = 0.604 | l = −32→32 |
51463 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.063 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.245 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.1178P)2] where P = (Fo2 + 2Fc2)/3 |
7599 reflections | (Δ/σ)max = 0.001 |
415 parameters | Δρmax = 1.24 e Å−3 |
199 restraints | Δρmin = −0.59 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 1.0396 (4) | 0.3019 (10) | 0.7744 (4) | 0.0594 (11) | |
C2 | 1.0914 (4) | 0.2828 (10) | 0.7602 (4) | 0.050 (2) | |
C3 | 1.1563 (4) | 0.2559 (12) | 0.7970 (4) | 0.061 (2) | |
H3 | 1.1731 | 0.2440 | 0.8364 | 0.073* | |
C4 | 1.1953 (4) | 0.2472 (14) | 0.7734 (5) | 0.074 (3) | |
H4 | 1.2397 | 0.2364 | 0.7971 | 0.089* | |
C5 | 1.1683 (4) | 0.2547 (13) | 0.7140 (6) | 0.071 (3) | |
H5 | 1.1952 | 0.2427 | 0.6986 | 0.085* | |
C6 | 1.1038 (5) | 0.2790 (11) | 0.6775 (4) | 0.062 (2) | |
H6 | 1.0865 | 0.2839 | 0.6379 | 0.074* | |
C7 | 1.0648 (4) | 0.2962 (9) | 0.7020 (4) | 0.048 (2) | |
C8 | 0.9946 (4) | 0.3326 (10) | 0.6747 (4) | 0.0594 (11) | |
H8 | 0.9847 | 0.4601 | 0.6567 | 0.071* | |
C9 | 0.8888 (4) | 0.2198 (10) | 0.5965 (4) | 0.0594 (6) | |
C10 | 0.8546 (5) | 0.0537 (10) | 0.5660 (4) | 0.074 (3) | |
H10 | 0.8741 | −0.0667 | 0.5732 | 0.089* | |
C11 | 0.7902 (5) | 0.0815 (16) | 0.5245 (4) | 0.077 (3) | |
H11 | 0.7666 | −0.0232 | 0.5025 | 0.093* | |
C12 | 0.7600 (5) | 0.257 (2) | 0.5146 (4) | 0.083 (3) | |
C13 | 0.7926 (5) | 0.4136 (17) | 0.5462 (5) | 0.086 (3) | |
H13 | 0.7723 | 0.5321 | 0.5403 | 0.103* | |
C14 | 0.8586 (5) | 0.3904 (13) | 0.5883 (4) | 0.073 (3) | |
H14 | 0.8816 | 0.4952 | 0.6107 | 0.088* | |
C15 | 0.2934 (5) | 0.7694 (15) | 0.2248 (5) | 0.0762 (13) | |
C16 | 0.2413 (4) | 0.7584 (12) | 0.2380 (4) | 0.0528 (19) | |
C17 | 0.1764 (4) | 0.7422 (13) | 0.2024 (4) | 0.067 (3) | |
H17 | 0.1588 | 0.7397 | 0.1627 | 0.081* | |
C18 | 0.1376 (4) | 0.7298 (12) | 0.2257 (5) | 0.069 (3) | |
H18 | 0.0934 | 0.7143 | 0.2021 | 0.082* | |
C19 | 0.1643 (5) | 0.7405 (12) | 0.2850 (5) | 0.069 (3) | |
H19 | 0.1372 | 0.7335 | 0.3003 | 0.082* | |
C20 | 0.2302 (4) | 0.7612 (13) | 0.3222 (4) | 0.065 (2) | |
H20 | 0.2479 | 0.7689 | 0.3618 | 0.078* | |
C21 | 0.2674 (4) | 0.7697 (13) | 0.2968 (4) | 0.060 (2) | |
C22 | 0.3393 (4) | 0.8189 (14) | 0.3257 (4) | 0.0762 (13) | |
H22 | 0.3475 | 0.9494 | 0.3416 | 0.091* | |
C23 | 0.4452 (5) | 0.7376 (16) | 0.4047 (4) | 0.0762 (7) | |
C24 | 0.4711 (5) | 0.9051 (12) | 0.4150 (5) | 0.102 (4) | |
H24 | 0.4468 | 1.0086 | 0.3927 | 0.122* | |
C25 | 0.5367 (5) | 0.9380 (17) | 0.4600 (5) | 0.096 (4) | |
H25 | 0.5534 | 1.0614 | 0.4707 | 0.116* | |
C26 | 0.5725 (5) | 0.7806 (17) | 0.4858 (5) | 0.078 (3) | |
C27 | 0.5460 (5) | 0.6024 (18) | 0.4688 (6) | 0.107 (4) | |
H27 | 0.5713 | 0.4930 | 0.4840 | 0.128* | |
C28 | 0.4817 (5) | 0.5855 (17) | 0.4291 (6) | 0.107 (4) | |
H28 | 0.4634 | 0.4637 | 0.4192 | 0.128* | |
C29 | 0.6267 (5) | 0.7193 (15) | 0.7252 (5) | 0.0794 (14) | |
C30 | 0.5755 (4) | 0.7268 (11) | 0.7389 (4) | 0.0497 (19) | |
C31 | 0.5094 (4) | 0.7330 (11) | 0.7027 (4) | 0.058 (2) | |
H31 | 0.4912 | 0.7332 | 0.6629 | 0.069* | |
C32 | 0.4714 (4) | 0.7391 (13) | 0.7282 (5) | 0.068 (3) | |
H32 | 0.4268 | 0.7451 | 0.7051 | 0.082* | |
C33 | 0.4986 (5) | 0.7365 (13) | 0.7869 (6) | 0.075 (3) | |
H33 | 0.4719 | 0.7398 | 0.8026 | 0.089* | |
C34 | 0.5647 (5) | 0.7291 (12) | 0.8232 (5) | 0.067 (2) | |
H34 | 0.5828 | 0.7281 | 0.8630 | 0.080* | |
C35 | 0.6028 (4) | 0.7233 (13) | 0.7980 (4) | 0.062 (2) | |
C36 | 0.6754 (5) | 0.6907 (15) | 0.8270 (4) | 0.0794 (14) | |
H36 | 0.6860 | 0.5625 | 0.8445 | 0.095* | |
C37 | 0.7781 (5) | 0.7872 (15) | 0.9045 (4) | 0.0794 (7) | |
C38 | 0.8105 (5) | 0.9382 (12) | 0.9313 (5) | 0.095 (3) | |
H38 | 0.7885 | 1.0547 | 0.9223 | 0.113* | |
C39 | 0.8742 (5) | 0.9409 (17) | 0.9718 (5) | 0.089 (3) | |
H39 | 0.8946 | 1.0557 | 0.9892 | 0.107* | |
C40 | 0.9076 (4) | 0.7718 (17) | 0.9865 (4) | 0.072 (3) | |
C41 | 0.8752 (6) | 0.6101 (17) | 0.9579 (5) | 0.088 (3) | |
H41 | 0.8964 | 0.4924 | 0.9674 | 0.106* | |
C42 | 0.8110 (5) | 0.6186 (18) | 0.9148 (5) | 0.094 (3) | |
H42 | 0.7906 | 0.5099 | 0.8931 | 0.112* | |
N1 | 0.9557 (3) | 0.1954 (8) | 0.6344 (3) | 0.0594 (6) | |
H1A | 0.9733 | 0.0900 | 0.6326 | 0.071* | |
N2 | 0.3773 (4) | 0.6921 (11) | 0.3654 (3) | 0.0762 (7) | |
H2A | 0.3620 | 0.5831 | 0.3679 | 0.091* | |
N3 | 0.7099 (4) | 0.8172 (11) | 0.8647 (3) | 0.0794 (7) | |
H3A | 0.6922 | 0.9224 | 0.8665 | 0.095* | |
O1 | 1.0417 (3) | 0.2936 (7) | 0.8199 (3) | 0.0652 (16) | |
O2 | 0.9836 (3) | 0.3329 (6) | 0.7255 (3) | 0.0594 (11) | |
O3 | 0.3488 (3) | 0.8083 (8) | 0.2729 (3) | 0.0762 (13) | |
O4 | 0.2912 (3) | 0.7678 (9) | 0.1794 (3) | 0.0709 (16) | |
O5 | 0.6833 (3) | 0.6934 (9) | 0.7742 (3) | 0.0794 (14) | |
O6 | 0.6247 (3) | 0.7182 (8) | 0.6800 (3) | 0.0702 (16) | |
I1 | 0.66517 (4) | 0.28578 (17) | 0.44660 (4) | 0.1202 (4) | |
I2 | 0.66745 (4) | 0.80655 (14) | 0.55354 (4) | 0.1101 (4) | |
I3 | 1.00157 (4) | 0.76622 (16) | 1.05464 (4) | 0.1114 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.055 (2) | 0.057 (2) | 0.069 (3) | 0.0026 (17) | 0.034 (2) | −0.0008 (19) |
C2 | 0.043 (5) | 0.040 (4) | 0.067 (6) | −0.005 (3) | 0.027 (4) | −0.009 (4) |
C3 | 0.051 (6) | 0.048 (4) | 0.071 (6) | −0.008 (4) | 0.022 (5) | −0.014 (5) |
C4 | 0.045 (5) | 0.057 (5) | 0.111 (9) | 0.003 (5) | 0.033 (6) | 0.002 (6) |
C5 | 0.054 (6) | 0.055 (5) | 0.121 (9) | 0.004 (5) | 0.056 (6) | −0.003 (6) |
C6 | 0.064 (6) | 0.059 (5) | 0.078 (6) | 0.007 (4) | 0.047 (5) | 0.001 (4) |
C7 | 0.044 (4) | 0.042 (4) | 0.061 (6) | −0.003 (3) | 0.028 (4) | 0.002 (3) |
C8 | 0.055 (2) | 0.057 (2) | 0.069 (3) | 0.0026 (17) | 0.034 (2) | −0.0008 (19) |
C9 | 0.0555 (4) | 0.0574 (10) | 0.0686 (4) | 0.0026 (4) | 0.0337 (10) | −0.0008 (5) |
C10 | 0.060 (6) | 0.080 (6) | 0.069 (6) | −0.007 (5) | 0.022 (5) | −0.006 (5) |
C11 | 0.057 (6) | 0.105 (7) | 0.063 (6) | −0.013 (5) | 0.025 (5) | −0.008 (5) |
C12 | 0.044 (6) | 0.139 (9) | 0.057 (6) | −0.010 (7) | 0.018 (5) | 0.000 (7) |
C13 | 0.051 (6) | 0.113 (8) | 0.079 (7) | 0.025 (5) | 0.021 (5) | 0.003 (6) |
C14 | 0.067 (6) | 0.067 (5) | 0.070 (6) | 0.009 (5) | 0.023 (5) | 0.010 (5) |
C15 | 0.049 (3) | 0.120 (4) | 0.065 (3) | −0.002 (2) | 0.033 (2) | 0.002 (2) |
C16 | 0.050 (5) | 0.049 (4) | 0.052 (5) | −0.004 (4) | 0.020 (4) | −0.012 (4) |
C17 | 0.041 (5) | 0.058 (5) | 0.091 (7) | −0.001 (4) | 0.024 (5) | −0.013 (5) |
C18 | 0.042 (5) | 0.058 (5) | 0.095 (8) | 0.003 (4) | 0.026 (5) | 0.004 (6) |
C19 | 0.058 (6) | 0.059 (5) | 0.108 (9) | 0.007 (5) | 0.057 (6) | 0.002 (6) |
C20 | 0.056 (6) | 0.062 (5) | 0.080 (6) | −0.001 (4) | 0.036 (5) | −0.011 (5) |
C21 | 0.048 (5) | 0.072 (5) | 0.060 (6) | −0.006 (4) | 0.027 (5) | −0.009 (4) |
C22 | 0.049 (3) | 0.120 (4) | 0.065 (3) | −0.002 (2) | 0.033 (2) | 0.002 (2) |
C23 | 0.0488 (5) | 0.1200 (16) | 0.0655 (4) | −0.0019 (5) | 0.0329 (12) | 0.0018 (5) |
C24 | 0.059 (6) | 0.148 (10) | 0.087 (8) | 0.010 (7) | 0.028 (6) | 0.062 (7) |
C25 | 0.059 (6) | 0.099 (8) | 0.119 (10) | −0.003 (6) | 0.036 (6) | 0.030 (7) |
C26 | 0.044 (6) | 0.117 (8) | 0.070 (7) | −0.014 (6) | 0.026 (5) | −0.013 (6) |
C27 | 0.047 (6) | 0.113 (9) | 0.125 (10) | −0.002 (6) | 0.017 (6) | −0.034 (7) |
C28 | 0.059 (7) | 0.109 (8) | 0.135 (11) | −0.013 (6) | 0.037 (7) | −0.044 (7) |
C29 | 0.051 (2) | 0.129 (4) | 0.067 (3) | −0.006 (2) | 0.036 (2) | −0.012 (3) |
C30 | 0.042 (4) | 0.047 (4) | 0.051 (5) | 0.002 (4) | 0.017 (4) | 0.009 (4) |
C31 | 0.037 (5) | 0.050 (4) | 0.063 (6) | 0.000 (4) | 0.008 (4) | 0.006 (4) |
C32 | 0.042 (5) | 0.056 (5) | 0.106 (9) | −0.006 (4) | 0.037 (6) | −0.004 (6) |
C33 | 0.065 (7) | 0.058 (5) | 0.119 (10) | −0.005 (5) | 0.060 (7) | −0.004 (7) |
C34 | 0.062 (6) | 0.057 (5) | 0.089 (7) | −0.006 (4) | 0.044 (6) | −0.003 (5) |
C35 | 0.040 (5) | 0.080 (6) | 0.064 (6) | −0.003 (4) | 0.026 (5) | 0.002 (5) |
C36 | 0.051 (2) | 0.129 (4) | 0.067 (3) | −0.006 (2) | 0.036 (2) | −0.012 (3) |
C37 | 0.0506 (5) | 0.1291 (15) | 0.0667 (4) | −0.0058 (5) | 0.0356 (12) | −0.0122 (5) |
C38 | 0.053 (6) | 0.134 (8) | 0.096 (8) | 0.013 (5) | 0.037 (6) | 0.017 (6) |
C39 | 0.059 (7) | 0.116 (9) | 0.098 (9) | −0.010 (6) | 0.044 (6) | −0.004 (6) |
C40 | 0.044 (5) | 0.115 (8) | 0.055 (6) | 0.011 (6) | 0.024 (5) | 0.011 (6) |
C41 | 0.071 (7) | 0.094 (7) | 0.101 (9) | −0.003 (6) | 0.045 (7) | −0.026 (6) |
C42 | 0.055 (6) | 0.141 (9) | 0.082 (8) | −0.025 (6) | 0.033 (6) | −0.050 (7) |
N1 | 0.0555 (4) | 0.0574 (10) | 0.0686 (4) | 0.0026 (4) | 0.0337 (10) | −0.0008 (5) |
N2 | 0.0488 (5) | 0.1200 (16) | 0.0655 (4) | −0.0019 (5) | 0.0329 (12) | 0.0018 (5) |
N3 | 0.0506 (5) | 0.1291 (15) | 0.0667 (4) | −0.0058 (5) | 0.0356 (12) | −0.0122 (5) |
O1 | 0.076 (4) | 0.065 (4) | 0.059 (4) | −0.005 (3) | 0.037 (3) | −0.004 (3) |
O2 | 0.055 (2) | 0.057 (2) | 0.069 (3) | 0.0026 (17) | 0.034 (2) | −0.0008 (19) |
O3 | 0.049 (3) | 0.120 (4) | 0.065 (3) | −0.002 (2) | 0.033 (2) | 0.002 (2) |
O4 | 0.079 (4) | 0.076 (4) | 0.062 (4) | 0.005 (3) | 0.039 (4) | 0.002 (3) |
O5 | 0.051 (2) | 0.129 (4) | 0.067 (3) | −0.006 (2) | 0.036 (2) | −0.012 (3) |
O6 | 0.078 (4) | 0.073 (4) | 0.063 (4) | −0.008 (3) | 0.038 (3) | −0.005 (3) |
I1 | 0.0473 (5) | 0.2083 (11) | 0.0794 (6) | 0.0065 (4) | 0.0127 (4) | 0.0218 (5) |
I2 | 0.0492 (4) | 0.1748 (9) | 0.0784 (5) | −0.0055 (4) | 0.0113 (4) | −0.0158 (5) |
I3 | 0.0475 (5) | 0.1938 (9) | 0.0711 (5) | −0.0034 (4) | 0.0138 (4) | 0.0037 (5) |
Geometric parameters (Å, º) top
C1—O1 | 1.201 (10) | C22—H22 | 0.9800 |
C1—O2 | 1.345 (10) | C23—C24 | 1.283 (11) |
C1—C2 | 1.479 (11) | C23—C28 | 1.319 (15) |
C2—C7 | 1.365 (11) | C23—N2 | 1.463 (12) |
C2—C3 | 1.376 (12) | C24—C25 | 1.444 (14) |
C3—C4 | 1.372 (12) | C24—H24 | 0.9300 |
C3—H3 | 0.9300 | C25—C26 | 1.349 (14) |
C4—C5 | 1.392 (14) | C25—H25 | 0.9300 |
C4—H4 | 0.9300 | C26—C27 | 1.363 (15) |
C5—C6 | 1.364 (12) | C26—I2 | 2.092 (10) |
C5—H5 | 0.9300 | C27—C28 | 1.370 (14) |
C6—C7 | 1.396 (11) | C27—H27 | 0.9300 |
C6—H6 | 0.9300 | C28—H28 | 0.9300 |
C7—C8 | 1.482 (11) | C29—O6 | 1.195 (11) |
C8—N1 | 1.393 (10) | C29—O5 | 1.349 (12) |
C8—O2 | 1.519 (11) | C29—C30 | 1.452 (12) |
C8—H8 | 0.9800 | C30—C31 | 1.383 (10) |
C9—C14 | 1.349 (11) | C30—C35 | 1.383 (11) |
C9—N1 | 1.415 (11) | C31—C32 | 1.392 (12) |
C9—C10 | 1.415 (10) | C31—H31 | 0.9300 |
C10—C11 | 1.393 (13) | C32—C33 | 1.373 (13) |
C10—H10 | 0.9300 | C32—H32 | 0.9300 |
C11—C12 | 1.372 (14) | C33—C34 | 1.383 (13) |
C11—H11 | 0.9300 | C33—H33 | 0.9300 |
C12—C13 | 1.363 (15) | C34—C35 | 1.388 (12) |
C12—I1 | 2.095 (10) | C34—H34 | 0.9300 |
C13—C14 | 1.420 (13) | C35—C36 | 1.527 (12) |
C13—H13 | 0.9300 | C36—N3 | 1.282 (11) |
C14—H14 | 0.9300 | C36—O5 | 1.526 (11) |
C15—O4 | 1.196 (10) | C36—H36 | 0.9800 |
C15—O3 | 1.336 (11) | C37—C38 | 1.291 (12) |
C15—C16 | 1.465 (11) | C37—C42 | 1.362 (15) |
C16—C17 | 1.364 (11) | C37—N3 | 1.451 (13) |
C16—C21 | 1.380 (11) | C38—C39 | 1.360 (14) |
C17—C18 | 1.364 (12) | C38—H38 | 0.9300 |
C17—H17 | 0.9300 | C39—C40 | 1.365 (14) |
C18—C19 | 1.392 (13) | C39—H39 | 0.9300 |
C18—H18 | 0.9300 | C40—C41 | 1.365 (14) |
C19—C20 | 1.389 (12) | C40—I3 | 2.071 (9) |
C19—H19 | 0.9300 | C41—C42 | 1.387 (15) |
C20—C21 | 1.374 (11) | C41—H41 | 0.9300 |
C20—H20 | 0.9300 | C42—H42 | 0.9300 |
C21—C22 | 1.534 (12) | N1—H1A | 0.8600 |
C22—N2 | 1.331 (11) | N2—H2A | 0.8600 |
C22—O3 | 1.549 (11) | N3—H3A | 0.8600 |
| | | |
O1—C1—O2 | 120.9 (8) | C28—C23—N2 | 114.0 (9) |
O1—C1—C2 | 130.5 (9) | C23—C24—C25 | 122.0 (10) |
O2—C1—C2 | 108.5 (8) | C23—C24—H24 | 119.0 |
C7—C2—C3 | 122.8 (8) | C25—C24—H24 | 119.0 |
C7—C2—C1 | 108.8 (8) | C26—C25—C24 | 116.6 (10) |
C3—C2—C1 | 128.4 (9) | C26—C25—H25 | 121.7 |
C4—C3—C2 | 117.6 (9) | C24—C25—H25 | 121.7 |
C4—C3—H3 | 121.2 | C25—C26—C27 | 119.8 (10) |
C2—C3—H3 | 121.2 | C25—C26—I2 | 120.8 (8) |
C3—C4—C5 | 119.9 (9) | C27—C26—I2 | 119.4 (9) |
C3—C4—H4 | 120.1 | C26—C27—C28 | 119.5 (12) |
C5—C4—H4 | 120.1 | C26—C27—H27 | 120.3 |
C6—C5—C4 | 122.4 (9) | C28—C27—H27 | 120.3 |
C6—C5—H5 | 118.8 | C23—C28—C27 | 121.7 (11) |
C4—C5—H5 | 118.8 | C23—C28—H28 | 119.1 |
C5—C6—C7 | 117.4 (9) | C27—C28—H28 | 119.1 |
C5—C6—H6 | 121.3 | O6—C29—O5 | 119.9 (9) |
C7—C6—H6 | 121.3 | O6—C29—C30 | 130.9 (10) |
C2—C7—C6 | 119.9 (8) | O5—C29—C30 | 108.8 (8) |
C2—C7—C8 | 109.9 (8) | C31—C30—C35 | 121.6 (8) |
C6—C7—C8 | 130.2 (8) | C31—C30—C29 | 129.8 (9) |
N1—C8—C7 | 114.8 (6) | C35—C30—C29 | 108.7 (8) |
N1—C8—O2 | 110.4 (6) | C30—C31—C32 | 117.2 (9) |
C7—C8—O2 | 102.9 (7) | C30—C31—H31 | 121.4 |
N1—C8—H8 | 109.5 | C32—C31—H31 | 121.4 |
C7—C8—H8 | 109.5 | C33—C32—C31 | 121.1 (9) |
O2—C8—H8 | 109.5 | C33—C32—H32 | 119.4 |
C14—C9—N1 | 122.9 (8) | C31—C32—H32 | 119.4 |
C14—C9—C10 | 121.1 (9) | C32—C33—C34 | 121.8 (10) |
N1—C9—C10 | 115.9 (7) | C32—C33—H33 | 119.1 |
C11—C10—C9 | 115.9 (8) | C34—C33—H33 | 119.1 |
C11—C10—H10 | 122.0 | C33—C34—C35 | 117.3 (10) |
C9—C10—H10 | 122.0 | C33—C34—H34 | 121.4 |
C12—C11—C10 | 122.9 (9) | C35—C34—H34 | 121.4 |
C12—C11—H11 | 118.5 | C30—C35—C34 | 121.0 (8) |
C10—C11—H11 | 118.5 | C30—C35—C36 | 110.4 (8) |
C13—C12—C11 | 120.6 (9) | C34—C35—C36 | 128.2 (9) |
C13—C12—I1 | 119.9 (10) | N3—C36—O5 | 113.3 (8) |
C11—C12—I1 | 119.4 (9) | N3—C36—C35 | 114.8 (8) |
C12—C13—C14 | 117.8 (10) | O5—C36—C35 | 99.7 (8) |
C12—C13—H13 | 121.1 | N3—C36—H36 | 109.5 |
C14—C13—H13 | 121.1 | O5—C36—H36 | 109.5 |
C9—C14—C13 | 121.5 (10) | C35—C36—H36 | 109.5 |
C9—C14—H14 | 119.3 | C38—C37—C42 | 117.5 (11) |
C13—C14—H14 | 119.3 | C38—C37—N3 | 115.8 (10) |
O4—C15—O3 | 120.3 (9) | C42—C37—N3 | 126.7 (9) |
O4—C15—C16 | 130.0 (9) | C37—C38—C39 | 125.3 (10) |
O3—C15—C16 | 109.2 (8) | C37—C38—H38 | 117.3 |
C17—C16—C21 | 120.6 (8) | C39—C38—H38 | 117.3 |
C17—C16—C15 | 130.4 (9) | C38—C39—C40 | 118.8 (10) |
C21—C16—C15 | 109.0 (8) | C38—C39—H39 | 120.6 |
C18—C17—C16 | 119.0 (9) | C40—C39—H39 | 120.6 |
C18—C17—H17 | 120.5 | C41—C40—C39 | 117.4 (10) |
C16—C17—H17 | 120.5 | C41—C40—I3 | 122.9 (9) |
C17—C18—C19 | 119.9 (9) | C39—C40—I3 | 119.5 (9) |
C17—C18—H18 | 120.0 | C40—C41—C42 | 121.1 (11) |
C19—C18—H18 | 120.0 | C40—C41—H41 | 119.5 |
C20—C19—C18 | 122.2 (9) | C42—C41—H41 | 119.5 |
C20—C19—H19 | 118.9 | C37—C42—C41 | 119.6 (10) |
C18—C19—H19 | 118.9 | C37—C42—H42 | 120.2 |
C21—C20—C19 | 115.8 (9) | C41—C42—H42 | 120.2 |
C21—C20—H20 | 122.1 | C8—N1—C9 | 123.6 (6) |
C19—C20—H20 | 122.1 | C8—N1—H1A | 118.2 |
C20—C21—C16 | 122.4 (8) | C9—N1—H1A | 118.2 |
C20—C21—C22 | 127.3 (8) | C22—N2—C23 | 120.1 (8) |
C16—C21—C22 | 109.9 (8) | C22—N2—H2A | 119.9 |
N2—C22—C21 | 113.7 (8) | C23—N2—H2A | 119.9 |
N2—C22—O3 | 110.3 (7) | C36—N3—C37 | 121.7 (9) |
C21—C22—O3 | 99.9 (7) | C36—N3—H3A | 119.1 |
N2—C22—H22 | 110.9 | C37—N3—H3A | 119.1 |
C21—C22—H22 | 110.9 | C1—O2—C8 | 109.9 (6) |
O3—C22—H22 | 110.9 | C15—O3—C22 | 111.5 (7) |
C24—C23—C28 | 119.5 (10) | C29—O5—C36 | 112.1 (7) |
C24—C23—N2 | 126.5 (10) | | |
| | | |
O1—C1—C2—C7 | 177.8 (8) | N2—C23—C28—C27 | −177.5 (12) |
O2—C1—C2—C7 | −2.1 (8) | C26—C27—C28—C23 | 3 (2) |
O1—C1—C2—C3 | −2.1 (14) | O6—C29—C30—C31 | 0.6 (19) |
O2—C1—C2—C3 | 177.9 (7) | O5—C29—C30—C31 | −173.2 (8) |
C7—C2—C3—C4 | 1.6 (13) | O6—C29—C30—C35 | 179.5 (11) |
C1—C2—C3—C4 | −178.4 (8) | O5—C29—C30—C35 | 5.7 (11) |
C2—C3—C4—C5 | −3.6 (14) | C35—C30—C31—C32 | 1.1 (13) |
C3—C4—C5—C6 | 2.9 (15) | C29—C30—C31—C32 | 179.9 (9) |
C4—C5—C6—C7 | −0.1 (13) | C30—C31—C32—C33 | −0.8 (14) |
C3—C2—C7—C6 | 1.1 (11) | C31—C32—C33—C34 | 0.5 (15) |
C1—C2—C7—C6 | −178.8 (7) | C32—C33—C34—C35 | −0.4 (14) |
C3—C2—C7—C8 | −177.7 (7) | C31—C30—C35—C34 | −1.0 (14) |
C1—C2—C7—C8 | 2.3 (8) | C29—C30—C35—C34 | 179.9 (9) |
C5—C6—C7—C2 | −1.9 (11) | C31—C30—C35—C36 | 172.8 (8) |
C5—C6—C7—C8 | 176.7 (7) | C29—C30—C35—C36 | −6.2 (11) |
C2—C7—C8—N1 | −121.6 (8) | C33—C34—C35—C30 | 0.6 (14) |
C6—C7—C8—N1 | 59.7 (11) | C33—C34—C35—C36 | −172.0 (9) |
C2—C7—C8—O2 | −1.6 (7) | C30—C35—C36—N3 | 125.7 (9) |
C6—C7—C8—O2 | 179.7 (7) | C34—C35—C36—N3 | −61.1 (14) |
C14—C9—C10—C11 | 4.8 (14) | C30—C35—C36—O5 | 4.3 (10) |
N1—C9—C10—C11 | −173.9 (9) | C34—C35—C36—O5 | 177.6 (9) |
C9—C10—C11—C12 | −2.4 (15) | C42—C37—C38—C39 | −4.3 (18) |
C10—C11—C12—C13 | −0.6 (16) | N3—C37—C38—C39 | 177.5 (10) |
C10—C11—C12—I1 | 175.0 (8) | C37—C38—C39—C40 | −0.7 (19) |
C11—C12—C13—C14 | 1.4 (16) | C38—C39—C40—C41 | 2.2 (16) |
I1—C12—C13—C14 | −174.2 (8) | C38—C39—C40—I3 | −172.8 (8) |
N1—C9—C14—C13 | 174.4 (9) | C39—C40—C41—C42 | 1.2 (16) |
C10—C9—C14—C13 | −4.2 (15) | I3—C40—C41—C42 | 176.0 (9) |
C12—C13—C14—C9 | 1.0 (16) | C38—C37—C42—C41 | 7.5 (17) |
O4—C15—C16—C17 | 0.5 (19) | N3—C37—C42—C41 | −174.5 (10) |
O3—C15—C16—C17 | 172.3 (9) | C40—C41—C42—C37 | −6.2 (18) |
O4—C15—C16—C21 | −178.7 (11) | C7—C8—N1—C9 | −168.5 (7) |
O3—C15—C16—C21 | −6.8 (11) | O2—C8—N1—C9 | 75.8 (9) |
C21—C16—C17—C18 | −2.6 (14) | C14—C9—N1—C8 | 12.5 (13) |
C15—C16—C17—C18 | 178.4 (9) | C10—C9—N1—C8 | −168.9 (8) |
C16—C17—C18—C19 | 2.2 (15) | C21—C22—N2—C23 | −167.6 (8) |
C17—C18—C19—C20 | −0.8 (14) | O3—C22—N2—C23 | 81.2 (10) |
C18—C19—C20—C21 | −0.3 (14) | C24—C23—N2—C22 | 17.1 (15) |
C19—C20—C21—C16 | 0.0 (14) | C28—C23—N2—C22 | −160.2 (10) |
C19—C20—C21—C22 | 171.1 (9) | O5—C36—N3—C37 | −79.5 (11) |
C17—C16—C21—C20 | 1.5 (15) | C35—C36—N3—C37 | 166.9 (8) |
C15—C16—C21—C20 | −179.3 (9) | C38—C37—N3—C36 | 165.2 (10) |
C17—C16—C21—C22 | −171.0 (8) | C42—C37—N3—C36 | −12.9 (16) |
C15—C16—C21—C22 | 8.2 (11) | O1—C1—O2—C8 | −178.9 (6) |
C20—C21—C22—N2 | 64.3 (13) | C2—C1—O2—C8 | 1.1 (7) |
C16—C21—C22—N2 | −123.7 (9) | N1—C8—O2—C1 | 123.2 (7) |
C20—C21—C22—O3 | −178.3 (9) | C7—C8—O2—C1 | 0.2 (7) |
C16—C21—C22—O3 | −6.3 (9) | O4—C15—O3—C22 | 175.3 (9) |
C28—C23—C24—C25 | −11.1 (18) | C16—C15—O3—C22 | 2.5 (10) |
N2—C23—C24—C25 | 171.7 (10) | N2—C22—O3—C15 | 122.1 (9) |
C23—C24—C25—C26 | 8.7 (18) | C21—C22—O3—C15 | 2.1 (9) |
C24—C25—C26—C27 | −0.1 (17) | O6—C29—O5—C36 | −177.5 (9) |
C24—C25—C26—I2 | −178.0 (8) | C30—C29—O5—C36 | −2.8 (11) |
C25—C26—C27—C28 | −5.6 (19) | N3—C36—O5—C29 | −123.3 (10) |
I2—C26—C27—C28 | 172.4 (11) | C35—C36—O5—C29 | −0.8 (10) |
C24—C23—C28—C27 | 5 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.86 | 2.54 | 3.040 (8) | 118 |
N2—H2A···O6ii | 0.86 | 2.56 | 3.093 (10) | 121 |
N3—H3A···O4iii | 0.86 | 2.61 | 3.116 (10) | 119 |
N3—H3A···I1iv | 0.86 | 3.26 | 4.003 (8) | 147 |
C8—H8···O1v | 0.98 | 2.56 | 3.344 (9) | 136 |
C22—H22···O6iii | 0.98 | 2.55 | 3.356 (11) | 139 |
C36—H36···O4ii | 0.98 | 2.52 | 3.313 (12) | 138 |
Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+2, −z+1; (iv) x, −y+3/2, z+1/2; (v) −x+2, y+1/2, −z+3/2. |