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Crystals of the title compound, C14H10INO2, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806051075/at2177sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806051075/at2177Isup2.hkl
Contains datablock I

CCDC reference: 633589

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](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

Computing details top

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(3H)-one top
Crystal data top
C14H10INO2F(000) = 2040
Mr = 351.13Dx = 1.801 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 36043 reflections
a = 24.017 (3) Åθ = 1.8–26.0°
b = 6.9536 (6) ŵ = 2.47 mm1
c = 26.924 (5) ÅT = 296 K
β = 120.207 (11)°Plate, pale yellow
V = 3885.9 (10) Å30.66 × 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 focus2725 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.075
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 1.5°
ω scansh = 2929
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 88
Tmin = 0.285, Tmax = 0.604l = 3232
51463 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.245H-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 parametersΔρmax = 1.24 e Å3
199 restraintsΔρmin = 0.59 e Å3
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
xyzUiso*/Ueq
C11.0396 (4)0.3019 (10)0.7744 (4)0.0594 (11)
C21.0914 (4)0.2828 (10)0.7602 (4)0.050 (2)
C31.1563 (4)0.2559 (12)0.7970 (4)0.061 (2)
H31.17310.24400.83640.073*
C41.1953 (4)0.2472 (14)0.7734 (5)0.074 (3)
H41.23970.23640.79710.089*
C51.1683 (4)0.2547 (13)0.7140 (6)0.071 (3)
H51.19520.24270.69860.085*
C61.1038 (5)0.2790 (11)0.6775 (4)0.062 (2)
H61.08650.28390.63790.074*
C71.0648 (4)0.2962 (9)0.7020 (4)0.048 (2)
C80.9946 (4)0.3326 (10)0.6747 (4)0.0594 (11)
H80.98470.46010.65670.071*
C90.8888 (4)0.2198 (10)0.5965 (4)0.0594 (6)
C100.8546 (5)0.0537 (10)0.5660 (4)0.074 (3)
H100.87410.06670.57320.089*
C110.7902 (5)0.0815 (16)0.5245 (4)0.077 (3)
H110.76660.02320.50250.093*
C120.7600 (5)0.257 (2)0.5146 (4)0.083 (3)
C130.7926 (5)0.4136 (17)0.5462 (5)0.086 (3)
H130.77230.53210.54030.103*
C140.8586 (5)0.3904 (13)0.5883 (4)0.073 (3)
H140.88160.49520.61070.088*
C150.2934 (5)0.7694 (15)0.2248 (5)0.0762 (13)
C160.2413 (4)0.7584 (12)0.2380 (4)0.0528 (19)
C170.1764 (4)0.7422 (13)0.2024 (4)0.067 (3)
H170.15880.73970.16270.081*
C180.1376 (4)0.7298 (12)0.2257 (5)0.069 (3)
H180.09340.71430.20210.082*
C190.1643 (5)0.7405 (12)0.2850 (5)0.069 (3)
H190.13720.73350.30030.082*
C200.2302 (4)0.7612 (13)0.3222 (4)0.065 (2)
H200.24790.76890.36180.078*
C210.2674 (4)0.7697 (13)0.2968 (4)0.060 (2)
C220.3393 (4)0.8189 (14)0.3257 (4)0.0762 (13)
H220.34750.94940.34160.091*
C230.4452 (5)0.7376 (16)0.4047 (4)0.0762 (7)
C240.4711 (5)0.9051 (12)0.4150 (5)0.102 (4)
H240.44681.00860.39270.122*
C250.5367 (5)0.9380 (17)0.4600 (5)0.096 (4)
H250.55341.06140.47070.116*
C260.5725 (5)0.7806 (17)0.4858 (5)0.078 (3)
C270.5460 (5)0.6024 (18)0.4688 (6)0.107 (4)
H270.57130.49300.48400.128*
C280.4817 (5)0.5855 (17)0.4291 (6)0.107 (4)
H280.46340.46370.41920.128*
C290.6267 (5)0.7193 (15)0.7252 (5)0.0794 (14)
C300.5755 (4)0.7268 (11)0.7389 (4)0.0497 (19)
C310.5094 (4)0.7330 (11)0.7027 (4)0.058 (2)
H310.49120.73320.66290.069*
C320.4714 (4)0.7391 (13)0.7282 (5)0.068 (3)
H320.42680.74510.70510.082*
C330.4986 (5)0.7365 (13)0.7869 (6)0.075 (3)
H330.47190.73980.80260.089*
C340.5647 (5)0.7291 (12)0.8232 (5)0.067 (2)
H340.58280.72810.86300.080*
C350.6028 (4)0.7233 (13)0.7980 (4)0.062 (2)
C360.6754 (5)0.6907 (15)0.8270 (4)0.0794 (14)
H360.68600.56250.84450.095*
C370.7781 (5)0.7872 (15)0.9045 (4)0.0794 (7)
C380.8105 (5)0.9382 (12)0.9313 (5)0.095 (3)
H380.78851.05470.92230.113*
C390.8742 (5)0.9409 (17)0.9718 (5)0.089 (3)
H390.89461.05570.98920.107*
C400.9076 (4)0.7718 (17)0.9865 (4)0.072 (3)
C410.8752 (6)0.6101 (17)0.9579 (5)0.088 (3)
H410.89640.49240.96740.106*
C420.8110 (5)0.6186 (18)0.9148 (5)0.094 (3)
H420.79060.50990.89310.112*
N10.9557 (3)0.1954 (8)0.6344 (3)0.0594 (6)
H1A0.97330.09000.63260.071*
N20.3773 (4)0.6921 (11)0.3654 (3)0.0762 (7)
H2A0.36200.58310.36790.091*
N30.7099 (4)0.8172 (11)0.8647 (3)0.0794 (7)
H3A0.69220.92240.86650.095*
O11.0417 (3)0.2936 (7)0.8199 (3)0.0652 (16)
O20.9836 (3)0.3329 (6)0.7255 (3)0.0594 (11)
O30.3488 (3)0.8083 (8)0.2729 (3)0.0762 (13)
O40.2912 (3)0.7678 (9)0.1794 (3)0.0709 (16)
O50.6833 (3)0.6934 (9)0.7742 (3)0.0794 (14)
O60.6247 (3)0.7182 (8)0.6800 (3)0.0702 (16)
I10.66517 (4)0.28578 (17)0.44660 (4)0.1202 (4)
I20.66745 (4)0.80655 (14)0.55354 (4)0.1101 (4)
I31.00157 (4)0.76622 (16)1.05464 (4)0.1114 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.055 (2)0.057 (2)0.069 (3)0.0026 (17)0.034 (2)0.0008 (19)
C20.043 (5)0.040 (4)0.067 (6)0.005 (3)0.027 (4)0.009 (4)
C30.051 (6)0.048 (4)0.071 (6)0.008 (4)0.022 (5)0.014 (5)
C40.045 (5)0.057 (5)0.111 (9)0.003 (5)0.033 (6)0.002 (6)
C50.054 (6)0.055 (5)0.121 (9)0.004 (5)0.056 (6)0.003 (6)
C60.064 (6)0.059 (5)0.078 (6)0.007 (4)0.047 (5)0.001 (4)
C70.044 (4)0.042 (4)0.061 (6)0.003 (3)0.028 (4)0.002 (3)
C80.055 (2)0.057 (2)0.069 (3)0.0026 (17)0.034 (2)0.0008 (19)
C90.0555 (4)0.0574 (10)0.0686 (4)0.0026 (4)0.0337 (10)0.0008 (5)
C100.060 (6)0.080 (6)0.069 (6)0.007 (5)0.022 (5)0.006 (5)
C110.057 (6)0.105 (7)0.063 (6)0.013 (5)0.025 (5)0.008 (5)
C120.044 (6)0.139 (9)0.057 (6)0.010 (7)0.018 (5)0.000 (7)
C130.051 (6)0.113 (8)0.079 (7)0.025 (5)0.021 (5)0.003 (6)
C140.067 (6)0.067 (5)0.070 (6)0.009 (5)0.023 (5)0.010 (5)
C150.049 (3)0.120 (4)0.065 (3)0.002 (2)0.033 (2)0.002 (2)
C160.050 (5)0.049 (4)0.052 (5)0.004 (4)0.020 (4)0.012 (4)
C170.041 (5)0.058 (5)0.091 (7)0.001 (4)0.024 (5)0.013 (5)
C180.042 (5)0.058 (5)0.095 (8)0.003 (4)0.026 (5)0.004 (6)
C190.058 (6)0.059 (5)0.108 (9)0.007 (5)0.057 (6)0.002 (6)
C200.056 (6)0.062 (5)0.080 (6)0.001 (4)0.036 (5)0.011 (5)
C210.048 (5)0.072 (5)0.060 (6)0.006 (4)0.027 (5)0.009 (4)
C220.049 (3)0.120 (4)0.065 (3)0.002 (2)0.033 (2)0.002 (2)
C230.0488 (5)0.1200 (16)0.0655 (4)0.0019 (5)0.0329 (12)0.0018 (5)
C240.059 (6)0.148 (10)0.087 (8)0.010 (7)0.028 (6)0.062 (7)
C250.059 (6)0.099 (8)0.119 (10)0.003 (6)0.036 (6)0.030 (7)
C260.044 (6)0.117 (8)0.070 (7)0.014 (6)0.026 (5)0.013 (6)
C270.047 (6)0.113 (9)0.125 (10)0.002 (6)0.017 (6)0.034 (7)
C280.059 (7)0.109 (8)0.135 (11)0.013 (6)0.037 (7)0.044 (7)
C290.051 (2)0.129 (4)0.067 (3)0.006 (2)0.036 (2)0.012 (3)
C300.042 (4)0.047 (4)0.051 (5)0.002 (4)0.017 (4)0.009 (4)
C310.037 (5)0.050 (4)0.063 (6)0.000 (4)0.008 (4)0.006 (4)
C320.042 (5)0.056 (5)0.106 (9)0.006 (4)0.037 (6)0.004 (6)
C330.065 (7)0.058 (5)0.119 (10)0.005 (5)0.060 (7)0.004 (7)
C340.062 (6)0.057 (5)0.089 (7)0.006 (4)0.044 (6)0.003 (5)
C350.040 (5)0.080 (6)0.064 (6)0.003 (4)0.026 (5)0.002 (5)
C360.051 (2)0.129 (4)0.067 (3)0.006 (2)0.036 (2)0.012 (3)
C370.0506 (5)0.1291 (15)0.0667 (4)0.0058 (5)0.0356 (12)0.0122 (5)
C380.053 (6)0.134 (8)0.096 (8)0.013 (5)0.037 (6)0.017 (6)
C390.059 (7)0.116 (9)0.098 (9)0.010 (6)0.044 (6)0.004 (6)
C400.044 (5)0.115 (8)0.055 (6)0.011 (6)0.024 (5)0.011 (6)
C410.071 (7)0.094 (7)0.101 (9)0.003 (6)0.045 (7)0.026 (6)
C420.055 (6)0.141 (9)0.082 (8)0.025 (6)0.033 (6)0.050 (7)
N10.0555 (4)0.0574 (10)0.0686 (4)0.0026 (4)0.0337 (10)0.0008 (5)
N20.0488 (5)0.1200 (16)0.0655 (4)0.0019 (5)0.0329 (12)0.0018 (5)
N30.0506 (5)0.1291 (15)0.0667 (4)0.0058 (5)0.0356 (12)0.0122 (5)
O10.076 (4)0.065 (4)0.059 (4)0.005 (3)0.037 (3)0.004 (3)
O20.055 (2)0.057 (2)0.069 (3)0.0026 (17)0.034 (2)0.0008 (19)
O30.049 (3)0.120 (4)0.065 (3)0.002 (2)0.033 (2)0.002 (2)
O40.079 (4)0.076 (4)0.062 (4)0.005 (3)0.039 (4)0.002 (3)
O50.051 (2)0.129 (4)0.067 (3)0.006 (2)0.036 (2)0.012 (3)
O60.078 (4)0.073 (4)0.063 (4)0.008 (3)0.038 (3)0.005 (3)
I10.0473 (5)0.2083 (11)0.0794 (6)0.0065 (4)0.0127 (4)0.0218 (5)
I20.0492 (4)0.1748 (9)0.0784 (5)0.0055 (4)0.0113 (4)0.0158 (5)
I30.0475 (5)0.1938 (9)0.0711 (5)0.0034 (4)0.0138 (4)0.0037 (5)
Geometric parameters (Å, º) top
C1—O11.201 (10)C22—H220.9800
C1—O21.345 (10)C23—C241.283 (11)
C1—C21.479 (11)C23—C281.319 (15)
C2—C71.365 (11)C23—N21.463 (12)
C2—C31.376 (12)C24—C251.444 (14)
C3—C41.372 (12)C24—H240.9300
C3—H30.9300C25—C261.349 (14)
C4—C51.392 (14)C25—H250.9300
C4—H40.9300C26—C271.363 (15)
C5—C61.364 (12)C26—I22.092 (10)
C5—H50.9300C27—C281.370 (14)
C6—C71.396 (11)C27—H270.9300
C6—H60.9300C28—H280.9300
C7—C81.482 (11)C29—O61.195 (11)
C8—N11.393 (10)C29—O51.349 (12)
C8—O21.519 (11)C29—C301.452 (12)
C8—H80.9800C30—C311.383 (10)
C9—C141.349 (11)C30—C351.383 (11)
C9—N11.415 (11)C31—C321.392 (12)
C9—C101.415 (10)C31—H310.9300
C10—C111.393 (13)C32—C331.373 (13)
C10—H100.9300C32—H320.9300
C11—C121.372 (14)C33—C341.383 (13)
C11—H110.9300C33—H330.9300
C12—C131.363 (15)C34—C351.388 (12)
C12—I12.095 (10)C34—H340.9300
C13—C141.420 (13)C35—C361.527 (12)
C13—H130.9300C36—N31.282 (11)
C14—H140.9300C36—O51.526 (11)
C15—O41.196 (10)C36—H360.9800
C15—O31.336 (11)C37—C381.291 (12)
C15—C161.465 (11)C37—C421.362 (15)
C16—C171.364 (11)C37—N31.451 (13)
C16—C211.380 (11)C38—C391.360 (14)
C17—C181.364 (12)C38—H380.9300
C17—H170.9300C39—C401.365 (14)
C18—C191.392 (13)C39—H390.9300
C18—H180.9300C40—C411.365 (14)
C19—C201.389 (12)C40—I32.071 (9)
C19—H190.9300C41—C421.387 (15)
C20—C211.374 (11)C41—H410.9300
C20—H200.9300C42—H420.9300
C21—C221.534 (12)N1—H1A0.8600
C22—N21.331 (11)N2—H2A0.8600
C22—O31.549 (11)N3—H3A0.8600
O1—C1—O2120.9 (8)C28—C23—N2114.0 (9)
O1—C1—C2130.5 (9)C23—C24—C25122.0 (10)
O2—C1—C2108.5 (8)C23—C24—H24119.0
C7—C2—C3122.8 (8)C25—C24—H24119.0
C7—C2—C1108.8 (8)C26—C25—C24116.6 (10)
C3—C2—C1128.4 (9)C26—C25—H25121.7
C4—C3—C2117.6 (9)C24—C25—H25121.7
C4—C3—H3121.2C25—C26—C27119.8 (10)
C2—C3—H3121.2C25—C26—I2120.8 (8)
C3—C4—C5119.9 (9)C27—C26—I2119.4 (9)
C3—C4—H4120.1C26—C27—C28119.5 (12)
C5—C4—H4120.1C26—C27—H27120.3
C6—C5—C4122.4 (9)C28—C27—H27120.3
C6—C5—H5118.8C23—C28—C27121.7 (11)
C4—C5—H5118.8C23—C28—H28119.1
C5—C6—C7117.4 (9)C27—C28—H28119.1
C5—C6—H6121.3O6—C29—O5119.9 (9)
C7—C6—H6121.3O6—C29—C30130.9 (10)
C2—C7—C6119.9 (8)O5—C29—C30108.8 (8)
C2—C7—C8109.9 (8)C31—C30—C35121.6 (8)
C6—C7—C8130.2 (8)C31—C30—C29129.8 (9)
N1—C8—C7114.8 (6)C35—C30—C29108.7 (8)
N1—C8—O2110.4 (6)C30—C31—C32117.2 (9)
C7—C8—O2102.9 (7)C30—C31—H31121.4
N1—C8—H8109.5C32—C31—H31121.4
C7—C8—H8109.5C33—C32—C31121.1 (9)
O2—C8—H8109.5C33—C32—H32119.4
C14—C9—N1122.9 (8)C31—C32—H32119.4
C14—C9—C10121.1 (9)C32—C33—C34121.8 (10)
N1—C9—C10115.9 (7)C32—C33—H33119.1
C11—C10—C9115.9 (8)C34—C33—H33119.1
C11—C10—H10122.0C33—C34—C35117.3 (10)
C9—C10—H10122.0C33—C34—H34121.4
C12—C11—C10122.9 (9)C35—C34—H34121.4
C12—C11—H11118.5C30—C35—C34121.0 (8)
C10—C11—H11118.5C30—C35—C36110.4 (8)
C13—C12—C11120.6 (9)C34—C35—C36128.2 (9)
C13—C12—I1119.9 (10)N3—C36—O5113.3 (8)
C11—C12—I1119.4 (9)N3—C36—C35114.8 (8)
C12—C13—C14117.8 (10)O5—C36—C3599.7 (8)
C12—C13—H13121.1N3—C36—H36109.5
C14—C13—H13121.1O5—C36—H36109.5
C9—C14—C13121.5 (10)C35—C36—H36109.5
C9—C14—H14119.3C38—C37—C42117.5 (11)
C13—C14—H14119.3C38—C37—N3115.8 (10)
O4—C15—O3120.3 (9)C42—C37—N3126.7 (9)
O4—C15—C16130.0 (9)C37—C38—C39125.3 (10)
O3—C15—C16109.2 (8)C37—C38—H38117.3
C17—C16—C21120.6 (8)C39—C38—H38117.3
C17—C16—C15130.4 (9)C38—C39—C40118.8 (10)
C21—C16—C15109.0 (8)C38—C39—H39120.6
C18—C17—C16119.0 (9)C40—C39—H39120.6
C18—C17—H17120.5C41—C40—C39117.4 (10)
C16—C17—H17120.5C41—C40—I3122.9 (9)
C17—C18—C19119.9 (9)C39—C40—I3119.5 (9)
C17—C18—H18120.0C40—C41—C42121.1 (11)
C19—C18—H18120.0C40—C41—H41119.5
C20—C19—C18122.2 (9)C42—C41—H41119.5
C20—C19—H19118.9C37—C42—C41119.6 (10)
C18—C19—H19118.9C37—C42—H42120.2
C21—C20—C19115.8 (9)C41—C42—H42120.2
C21—C20—H20122.1C8—N1—C9123.6 (6)
C19—C20—H20122.1C8—N1—H1A118.2
C20—C21—C16122.4 (8)C9—N1—H1A118.2
C20—C21—C22127.3 (8)C22—N2—C23120.1 (8)
C16—C21—C22109.9 (8)C22—N2—H2A119.9
N2—C22—C21113.7 (8)C23—N2—H2A119.9
N2—C22—O3110.3 (7)C36—N3—C37121.7 (9)
C21—C22—O399.9 (7)C36—N3—H3A119.1
N2—C22—H22110.9C37—N3—H3A119.1
C21—C22—H22110.9C1—O2—C8109.9 (6)
O3—C22—H22110.9C15—O3—C22111.5 (7)
C24—C23—C28119.5 (10)C29—O5—C36112.1 (7)
C24—C23—N2126.5 (10)
O1—C1—C2—C7177.8 (8)N2—C23—C28—C27177.5 (12)
O2—C1—C2—C72.1 (8)C26—C27—C28—C233 (2)
O1—C1—C2—C32.1 (14)O6—C29—C30—C310.6 (19)
O2—C1—C2—C3177.9 (7)O5—C29—C30—C31173.2 (8)
C7—C2—C3—C41.6 (13)O6—C29—C30—C35179.5 (11)
C1—C2—C3—C4178.4 (8)O5—C29—C30—C355.7 (11)
C2—C3—C4—C53.6 (14)C35—C30—C31—C321.1 (13)
C3—C4—C5—C62.9 (15)C29—C30—C31—C32179.9 (9)
C4—C5—C6—C70.1 (13)C30—C31—C32—C330.8 (14)
C3—C2—C7—C61.1 (11)C31—C32—C33—C340.5 (15)
C1—C2—C7—C6178.8 (7)C32—C33—C34—C350.4 (14)
C3—C2—C7—C8177.7 (7)C31—C30—C35—C341.0 (14)
C1—C2—C7—C82.3 (8)C29—C30—C35—C34179.9 (9)
C5—C6—C7—C21.9 (11)C31—C30—C35—C36172.8 (8)
C5—C6—C7—C8176.7 (7)C29—C30—C35—C366.2 (11)
C2—C7—C8—N1121.6 (8)C33—C34—C35—C300.6 (14)
C6—C7—C8—N159.7 (11)C33—C34—C35—C36172.0 (9)
C2—C7—C8—O21.6 (7)C30—C35—C36—N3125.7 (9)
C6—C7—C8—O2179.7 (7)C34—C35—C36—N361.1 (14)
C14—C9—C10—C114.8 (14)C30—C35—C36—O54.3 (10)
N1—C9—C10—C11173.9 (9)C34—C35—C36—O5177.6 (9)
C9—C10—C11—C122.4 (15)C42—C37—C38—C394.3 (18)
C10—C11—C12—C130.6 (16)N3—C37—C38—C39177.5 (10)
C10—C11—C12—I1175.0 (8)C37—C38—C39—C400.7 (19)
C11—C12—C13—C141.4 (16)C38—C39—C40—C412.2 (16)
I1—C12—C13—C14174.2 (8)C38—C39—C40—I3172.8 (8)
N1—C9—C14—C13174.4 (9)C39—C40—C41—C421.2 (16)
C10—C9—C14—C134.2 (15)I3—C40—C41—C42176.0 (9)
C12—C13—C14—C91.0 (16)C38—C37—C42—C417.5 (17)
O4—C15—C16—C170.5 (19)N3—C37—C42—C41174.5 (10)
O3—C15—C16—C17172.3 (9)C40—C41—C42—C376.2 (18)
O4—C15—C16—C21178.7 (11)C7—C8—N1—C9168.5 (7)
O3—C15—C16—C216.8 (11)O2—C8—N1—C975.8 (9)
C21—C16—C17—C182.6 (14)C14—C9—N1—C812.5 (13)
C15—C16—C17—C18178.4 (9)C10—C9—N1—C8168.9 (8)
C16—C17—C18—C192.2 (15)C21—C22—N2—C23167.6 (8)
C17—C18—C19—C200.8 (14)O3—C22—N2—C2381.2 (10)
C18—C19—C20—C210.3 (14)C24—C23—N2—C2217.1 (15)
C19—C20—C21—C160.0 (14)C28—C23—N2—C22160.2 (10)
C19—C20—C21—C22171.1 (9)O5—C36—N3—C3779.5 (11)
C17—C16—C21—C201.5 (15)C35—C36—N3—C37166.9 (8)
C15—C16—C21—C20179.3 (9)C38—C37—N3—C36165.2 (10)
C17—C16—C21—C22171.0 (8)C42—C37—N3—C3612.9 (16)
C15—C16—C21—C228.2 (11)O1—C1—O2—C8178.9 (6)
C20—C21—C22—N264.3 (13)C2—C1—O2—C81.1 (7)
C16—C21—C22—N2123.7 (9)N1—C8—O2—C1123.2 (7)
C20—C21—C22—O3178.3 (9)C7—C8—O2—C10.2 (7)
C16—C21—C22—O36.3 (9)O4—C15—O3—C22175.3 (9)
C28—C23—C24—C2511.1 (18)C16—C15—O3—C222.5 (10)
N2—C23—C24—C25171.7 (10)N2—C22—O3—C15122.1 (9)
C23—C24—C25—C268.7 (18)C21—C22—O3—C152.1 (9)
C24—C25—C26—C270.1 (17)O6—C29—O5—C36177.5 (9)
C24—C25—C26—I2178.0 (8)C30—C29—O5—C362.8 (11)
C25—C26—C27—C285.6 (19)N3—C36—O5—C29123.3 (10)
I2—C26—C27—C28172.4 (11)C35—C36—O5—C290.8 (10)
C24—C23—C28—C275 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.862.543.040 (8)118
N2—H2A···O6ii0.862.563.093 (10)121
N3—H3A···O4iii0.862.613.116 (10)119
N3—H3A···I1iv0.863.264.003 (8)147
C8—H8···O1v0.982.563.344 (9)136
C22—H22···O6iii0.982.553.356 (11)139
C36—H36···O4ii0.982.523.313 (12)138
Symmetry codes: (i) x+2, y1/2, 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.
 

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