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The asymmetric unit of the title compound (systematic name: N,N′,N′′-tribenzyl­oxyiminodicarbonic diamide), C23H23N3O5, consists of two mol­ecules. In the crystalline state, the mol­ecules are assembled into centrosymmetric dimers by strong N—H...O=C inter­molecular hydrogen bonds. The results of IR and NMR spectroscopic analysis are in good agreement with the crystallographic study.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806004582/bv2002sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806004582/bv2002Isup2.hkl
Contains datablock I

CCDC reference: 601129

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.047
  • wR factor = 0.149
  • Data-to-parameter ratio = 10.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT430_ALERT_2_B Short Inter D...A Contact O13 .. O13 .. 2.68 Ang. PLAT430_ALERT_2_B Short Inter D...A Contact O23 .. O23 .. 2.68 Ang.
Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C122 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C112 PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C112 -C117 1.37 Ang. PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C118 -C123 1.37 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H11N .. O13 .. 2.75 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H21N .. O23 .. 2.66 Ang.
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 6 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 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

N,N',N''-tribenzyloxyiminodicarbonic diamide top
Crystal data top
C23H23N3O5Z = 4
Mr = 421.44F(000) = 888
Triclinic, P1Dx = 1.285 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.9947 (17) ÅCell parameters from 1132 reflections
b = 13.820 (3) Åθ = 4.6–27.5°
c = 18.714 (3) ŵ = 0.09 mm1
α = 100.763 (14)°T = 295 K
β = 90.447 (14)°Prism, colorless
γ = 107.227 (16)°0.60 × 0.36 × 0.21 mm
V = 2177.9 (8) Å3
Data collection top
Oxford Diffraction Xcalibur CCD
diffractometer
5022 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
Graphite monochromatorθmax = 25.0°, θmin = 4.0°
ω scansh = 910
16124 measured reflectionsk = 1614
7635 independent reflectionsl = 2222
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048All H-atom parameters refined
wR(F2) = 0.149 w = 1/[σ2(Fo2) + (0.0919P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
7635 reflectionsΔρmax = 0.23 e Å3
744 parametersΔρmin = 0.22 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0052 (13)
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
C110.4860 (2)0.57202 (17)0.13221 (13)0.0583 (5)
C120.2960 (2)0.55625 (15)0.00449 (11)0.0475 (5)
C130.0713 (3)0.32353 (16)0.01483 (15)0.0596 (6)
C140.1639 (2)0.54097 (15)0.12038 (10)0.0511 (5)
C150.3502 (3)0.6692 (2)0.28214 (12)0.0700 (7)
C160.6071 (2)0.67069 (15)0.13750 (11)0.0509 (5)
C170.6322 (3)0.75761 (17)0.08268 (13)0.0595 (5)
C180.7485 (3)0.8466 (2)0.08613 (17)0.0759 (7)
C190.8413 (4)0.8500 (3)0.14379 (19)0.0911 (9)
C250.8465 (3)0.6692 (2)0.26311 (13)0.0671 (6)
C240.6657 (2)0.54022 (15)0.39007 (10)0.0484 (5)
C230.5708 (3)0.32404 (16)0.43819 (14)0.0573 (5)
C220.8005 (2)0.55752 (14)0.51134 (11)0.0474 (5)
C210.9866 (2)0.57550 (17)0.65548 (14)0.0592 (5)
C2280.8234 (2)0.75369 (16)0.22898 (11)0.0568 (5)
C2230.9016 (3)0.8559 (2)0.25854 (14)0.0841 (8)
C2220.8760 (4)0.9340 (2)0.22820 (17)0.0976 (10)
C2210.7740 (4)0.9109 (2)0.16821 (16)0.0851 (8)
C1100.8189 (3)0.7653 (3)0.19797 (17)0.0858 (8)
C1110.7008 (3)0.6755 (2)0.19610 (13)0.0660 (6)
C1120.0805 (2)0.24652 (14)0.01588 (12)0.0532 (5)
C1130.1172 (3)0.2190 (2)0.08933 (15)0.0804 (7)
C1140.2575 (4)0.1470 (3)0.1173 (2)0.1006 (10)
C1150.3603 (4)0.1024 (2)0.0721 (3)0.0973 (10)
C1160.3278 (4)0.1304 (2)0.0010 (3)0.0994 (10)
C1170.1889 (3)0.2022 (2)0.02929 (17)0.0794 (7)
C1180.3336 (2)0.75402 (16)0.34099 (11)0.0557 (5)
C1190.2335 (3)0.73244 (18)0.39478 (12)0.0578 (5)
C1200.2161 (3)0.8098 (2)0.44873 (15)0.0716 (7)
C1210.2976 (4)0.9092 (2)0.44898 (17)0.0872 (8)
C1220.3974 (4)0.9323 (2)0.3955 (2)0.1037 (11)
C1230.4166 (4)0.8551 (2)0.34166 (16)0.0843 (8)
C2200.6968 (3)0.81077 (18)0.13857 (14)0.0690 (6)
C2190.7204 (3)0.73266 (17)0.16947 (12)0.0573 (5)
C2120.4146 (2)0.25025 (14)0.44407 (11)0.0508 (5)
C2170.3153 (3)0.20360 (19)0.38248 (15)0.0725 (6)
C2160.1716 (4)0.1358 (2)0.3875 (2)0.0923 (9)
C2150.1223 (4)0.1158 (2)0.4530 (2)0.0884 (9)
C2140.2174 (4)0.1615 (2)0.5148 (2)0.0803 (8)
C2130.3642 (3)0.22897 (18)0.51034 (14)0.0649 (6)
C261.1113 (2)0.67332 (15)0.68792 (11)0.0513 (5)
C2111.2052 (3)0.6782 (2)0.74839 (13)0.0675 (6)
C2101.3267 (3)0.7666 (2)0.77465 (16)0.0857 (8)
C291.3539 (3)0.8505 (2)0.74203 (17)0.0847 (8)
C281.2599 (3)0.8466 (2)0.68295 (16)0.0743 (7)
C271.1403 (3)0.75911 (17)0.65572 (13)0.0585 (5)
N110.2589 (2)0.52505 (13)0.06847 (9)0.0503 (4)
N120.19127 (17)0.50087 (12)0.04792 (8)0.0483 (4)
N130.2936 (2)0.60930 (15)0.15788 (10)0.0618 (5)
N230.7960 (2)0.60574 (14)0.37012 (10)0.0569 (4)
N220.69409 (17)0.50026 (11)0.45207 (8)0.0470 (4)
N210.7617 (2)0.53005 (13)0.57628 (9)0.0508 (4)
O110.34687 (15)0.59685 (10)0.10859 (7)0.0554 (4)
O120.41561 (16)0.62236 (11)0.03163 (8)0.0613 (4)
O130.05955 (14)0.42515 (9)0.01034 (7)0.0484 (3)
O140.03898 (17)0.50977 (12)0.14511 (8)0.0651 (4)
O150.26213 (17)0.67409 (12)0.21962 (7)0.0681 (4)
O250.76378 (17)0.67237 (11)0.32762 (8)0.0648 (4)
O240.53865 (16)0.51079 (12)0.35762 (8)0.0632 (4)
O230.56165 (14)0.42660 (9)0.46911 (7)0.0474 (3)
O220.92132 (16)0.62112 (11)0.50195 (8)0.0597 (4)
O210.85086 (15)0.60281 (10)0.63599 (7)0.0553 (4)
H11A0.517 (3)0.5341 (16)0.0950 (13)0.070 (6)*
H11B0.461 (2)0.5185 (17)0.1790 (14)0.074 (7)*
H11N0.159 (3)0.5010 (17)0.0853 (13)0.069 (7)*
H13A0.088 (3)0.3217 (16)0.0636 (14)0.070 (7)*
H13B0.159 (3)0.314 (2)0.0191 (16)0.099 (8)*
H13N0.364 (3)0.6430 (18)0.1318 (14)0.075 (8)*
H15A0.463 (3)0.6852 (18)0.2689 (13)0.081 (7)*
H15B0.302 (4)0.597 (3)0.292 (2)0.138 (13)*
H170.573 (3)0.7568 (16)0.0432 (13)0.067 (6)*
H180.762 (3)0.902 (2)0.0496 (15)0.088 (9)*
H190.912 (4)0.907 (3)0.1469 (19)0.125 (12)*
H25A0.955 (4)0.689 (2)0.2827 (16)0.102 (9)*
H25B0.797 (4)0.593 (3)0.2309 (18)0.120 (11)*
H23N0.868 (3)0.6376 (18)0.4076 (14)0.076 (7)*
H23A0.659 (3)0.3140 (17)0.4673 (13)0.079 (7)*
H23B0.595 (3)0.3225 (16)0.3861 (14)0.068 (6)*
H21N0.660 (3)0.5108 (16)0.5854 (12)0.066 (7)*
H21B0.958 (3)0.5300 (18)0.6917 (14)0.077 (7)*
H21A1.022 (3)0.5338 (17)0.6078 (14)0.078 (7)*
H2230.972 (3)0.871 (2)0.3017 (18)0.107 (9)*
H2220.932 (3)1.007 (2)0.2506 (15)0.107 (9)*
H2210.760 (3)0.970 (2)0.1496 (18)0.118 (10)*
H1100.885 (4)0.767 (2)0.2421 (18)0.111 (9)*
H1110.684 (3)0.614 (2)0.2345 (16)0.094 (8)*
H1130.046 (3)0.264 (2)0.1203 (16)0.094 (8)*
H1140.285 (4)0.132 (2)0.169 (2)0.115 (10)*
H1150.456 (5)0.053 (3)0.095 (2)0.139 (12)*
H1160.401 (4)0.104 (3)0.036 (2)0.127 (11)*
H1170.155 (3)0.226 (2)0.0819 (18)0.103 (9)*
H1190.172 (3)0.660 (2)0.3955 (13)0.085 (8)*
H1200.153 (3)0.794 (2)0.4846 (17)0.099 (9)*
H1210.281 (3)0.959 (2)0.4869 (18)0.109 (10)*
H1220.449 (4)0.999 (3)0.3928 (18)0.121 (11)*
H1230.484 (3)0.869 (2)0.3038 (17)0.099 (9)*
H2200.624 (3)0.796 (2)0.0966 (16)0.095 (8)*
H2190.666 (2)0.6627 (17)0.1484 (12)0.062 (6)*
H2170.352 (3)0.221 (2)0.3340 (16)0.095 (8)*
H2160.102 (4)0.108 (3)0.343 (2)0.133 (12)*
H2150.017 (4)0.067 (2)0.4551 (15)0.100 (9)*
H2140.191 (3)0.151 (2)0.5615 (17)0.098 (9)*
H2130.431 (3)0.2619 (16)0.5524 (13)0.066 (6)*
H2111.188 (3)0.622 (2)0.7716 (16)0.093 (9)*
H2101.388 (3)0.7679 (19)0.8147 (16)0.094 (8)*
H291.429 (4)0.913 (2)0.7600 (17)0.108 (10)*
H281.273 (3)0.9088 (19)0.6651 (14)0.079 (7)*
H271.079 (3)0.7568 (17)0.6146 (14)0.073 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C110.0496 (12)0.0632 (13)0.0591 (14)0.0158 (11)0.0120 (10)0.0069 (12)
C120.0403 (11)0.0517 (11)0.0495 (12)0.0117 (9)0.0028 (9)0.0115 (9)
C130.0563 (13)0.0556 (13)0.0680 (16)0.0161 (10)0.0032 (11)0.0166 (11)
C140.0466 (12)0.0637 (12)0.0436 (11)0.0171 (10)0.0001 (9)0.0115 (9)
C150.0747 (17)0.0933 (19)0.0430 (12)0.0341 (15)0.0031 (11)0.0020 (12)
C160.0440 (11)0.0624 (12)0.0492 (11)0.0178 (9)0.0042 (9)0.0155 (10)
C170.0574 (13)0.0703 (14)0.0535 (13)0.0209 (11)0.0092 (11)0.0161 (11)
C180.0728 (17)0.0618 (15)0.0860 (19)0.0095 (13)0.0055 (14)0.0153 (14)
C190.0757 (19)0.084 (2)0.111 (3)0.0055 (16)0.0230 (17)0.0430 (19)
C250.0720 (17)0.0851 (17)0.0511 (13)0.0257 (14)0.0155 (11)0.0268 (12)
C240.0479 (12)0.0577 (11)0.0422 (11)0.0187 (10)0.0084 (9)0.0112 (9)
C230.0543 (13)0.0513 (12)0.0666 (15)0.0186 (10)0.0105 (11)0.0080 (10)
C220.0441 (11)0.0478 (10)0.0508 (12)0.0134 (9)0.0046 (9)0.0122 (9)
C210.0518 (12)0.0645 (13)0.0648 (15)0.0178 (11)0.0038 (10)0.0214 (12)
C2280.0573 (12)0.0613 (12)0.0476 (12)0.0085 (10)0.0115 (9)0.0159 (10)
C2230.0945 (19)0.0817 (18)0.0546 (15)0.0075 (15)0.0160 (13)0.0170 (13)
C2220.127 (3)0.0604 (16)0.0784 (19)0.0116 (16)0.0161 (17)0.0146 (14)
C2210.108 (2)0.0624 (16)0.0794 (18)0.0121 (15)0.0023 (16)0.0241 (13)
C1100.0776 (18)0.105 (2)0.0807 (19)0.0234 (17)0.0321 (15)0.0384 (17)
C1110.0594 (14)0.0805 (16)0.0612 (14)0.0221 (13)0.0169 (11)0.0196 (13)
C1120.0508 (12)0.0488 (11)0.0619 (13)0.0157 (9)0.0050 (10)0.0140 (10)
C1130.0721 (17)0.0903 (18)0.0639 (16)0.0029 (14)0.0027 (13)0.0146 (14)
C1140.101 (2)0.094 (2)0.086 (2)0.0067 (19)0.0245 (19)0.0037 (18)
C1150.0706 (19)0.0642 (17)0.143 (3)0.0003 (15)0.017 (2)0.0206 (19)
C1160.075 (2)0.0770 (18)0.138 (3)0.0008 (16)0.030 (2)0.040 (2)
C1170.0824 (18)0.0685 (15)0.0810 (19)0.0097 (14)0.0226 (15)0.0198 (14)
C1180.0576 (12)0.0638 (13)0.0419 (11)0.0147 (10)0.0031 (9)0.0075 (9)
C1190.0598 (13)0.0577 (13)0.0545 (13)0.0155 (11)0.0014 (10)0.0114 (10)
C1200.0817 (17)0.0783 (18)0.0599 (15)0.0315 (14)0.0120 (13)0.0142 (13)
C1210.113 (2)0.0714 (18)0.0758 (19)0.0357 (17)0.0053 (16)0.0028 (15)
C1220.128 (3)0.0581 (17)0.104 (3)0.0032 (17)0.000 (2)0.0159 (17)
C1230.0918 (19)0.0773 (18)0.0689 (17)0.0005 (15)0.0136 (15)0.0187 (14)
C2200.0687 (15)0.0689 (15)0.0636 (15)0.0108 (12)0.0067 (12)0.0157 (12)
C2190.0560 (13)0.0524 (12)0.0566 (13)0.0070 (10)0.0057 (10)0.0090 (10)
C2120.0520 (11)0.0420 (10)0.0589 (13)0.0162 (9)0.0030 (9)0.0079 (9)
C2170.0767 (17)0.0651 (14)0.0678 (16)0.0131 (13)0.0093 (13)0.0077 (12)
C2160.0731 (19)0.0792 (18)0.106 (3)0.0069 (15)0.0208 (18)0.0007 (17)
C2150.0622 (17)0.0544 (15)0.140 (3)0.0081 (13)0.0094 (19)0.0140 (17)
C2140.087 (2)0.0654 (15)0.094 (2)0.0229 (15)0.0335 (17)0.0268 (15)
C2130.0712 (16)0.0620 (13)0.0593 (15)0.0168 (12)0.0043 (12)0.0116 (11)
C260.0445 (11)0.0636 (12)0.0479 (11)0.0190 (10)0.0051 (8)0.0121 (9)
C2110.0652 (15)0.0788 (16)0.0606 (14)0.0242 (13)0.0075 (11)0.0157 (13)
C2100.0765 (18)0.104 (2)0.0705 (17)0.0290 (17)0.0248 (14)0.0006 (16)
C290.0670 (17)0.0730 (17)0.099 (2)0.0120 (14)0.0116 (15)0.0048 (16)
C280.0685 (16)0.0612 (15)0.0877 (18)0.0109 (13)0.0054 (13)0.0153 (13)
C270.0587 (13)0.0658 (14)0.0527 (13)0.0199 (11)0.0045 (10)0.0140 (11)
N110.0412 (10)0.0632 (10)0.0422 (9)0.0071 (8)0.0041 (7)0.0140 (8)
N120.0398 (9)0.0559 (9)0.0422 (9)0.0059 (7)0.0003 (7)0.0069 (7)
N130.0509 (11)0.0800 (12)0.0436 (10)0.0132 (10)0.0021 (8)0.0039 (9)
N230.0507 (10)0.0679 (11)0.0570 (11)0.0146 (9)0.0067 (9)0.0293 (9)
N220.0409 (9)0.0525 (9)0.0457 (9)0.0075 (7)0.0054 (7)0.0155 (7)
N210.0427 (10)0.0616 (10)0.0444 (10)0.0096 (8)0.0012 (7)0.0117 (8)
O110.0465 (8)0.0696 (9)0.0559 (8)0.0183 (7)0.0100 (6)0.0252 (7)
O120.0482 (8)0.0695 (9)0.0522 (8)0.0013 (7)0.0004 (6)0.0087 (7)
O130.0401 (7)0.0503 (7)0.0499 (8)0.0061 (6)0.0037 (6)0.0105 (6)
O140.0495 (9)0.0933 (11)0.0481 (8)0.0137 (8)0.0064 (7)0.0159 (7)
O150.0720 (10)0.0868 (10)0.0443 (8)0.0328 (9)0.0057 (7)0.0038 (7)
O250.0735 (10)0.0793 (10)0.0570 (9)0.0334 (8)0.0220 (7)0.0340 (7)
O240.0505 (9)0.0855 (10)0.0521 (8)0.0140 (8)0.0016 (7)0.0209 (7)
O230.0428 (7)0.0443 (7)0.0523 (8)0.0086 (6)0.0081 (6)0.0106 (6)
O220.0493 (8)0.0667 (9)0.0562 (9)0.0020 (7)0.0026 (6)0.0204 (7)
O210.0468 (8)0.0699 (9)0.0480 (8)0.0206 (7)0.0012 (6)0.0040 (6)
Geometric parameters (Å, º) top
C11—O111.444 (2)C112—C1171.376 (3)
C11—C161.493 (3)C113—C1141.382 (4)
C11—H11A1.03 (2)C113—H1131.02 (3)
C11—H11B1.01 (2)C114—C1151.348 (5)
C12—O121.219 (2)C114—H1140.96 (3)
C12—N111.360 (3)C115—C1161.355 (5)
C12—N121.397 (2)C115—H1150.97 (4)
C13—O131.457 (3)C116—C1171.373 (4)
C13—C1121.492 (3)C116—H1160.97 (4)
C13—H13A0.93 (3)C117—H1170.99 (3)
C13—H13B1.04 (3)C118—C1191.371 (3)
C14—O141.207 (2)C118—C1231.372 (3)
C14—N131.354 (3)C119—C1201.373 (3)
C14—N121.418 (2)C119—H1191.00 (3)
C15—O151.431 (3)C120—C1211.351 (4)
C15—C1181.494 (3)C120—H1200.90 (3)
C15—H15A1.01 (3)C121—C1221.368 (5)
C15—H15B1.02 (4)C121—H1210.94 (3)
C16—C171.386 (3)C122—C1231.376 (4)
C16—C1111.388 (3)C122—H1220.91 (3)
C17—C181.371 (3)C123—H1230.95 (3)
C17—H170.91 (2)C220—C2191.382 (3)
C18—C191.368 (4)C220—H2200.97 (3)
C18—H180.91 (3)C219—H2190.95 (2)
C19—C1101.361 (4)C212—C2131.377 (3)
C19—H190.86 (3)C212—C2171.381 (3)
C25—O251.424 (3)C217—C2161.369 (4)
C25—C2281.495 (3)C217—H2171.01 (3)
C25—H25A0.98 (3)C216—C2151.357 (5)
C25—H25B1.07 (3)C216—H2160.97 (4)
C24—O241.209 (2)C215—C2141.364 (4)
C24—N231.355 (3)C215—H2150.99 (3)
C24—N221.426 (2)C214—C2131.386 (4)
C23—O231.454 (2)C214—H2140.93 (3)
C23—C2121.491 (3)C213—H2130.94 (2)
C23—H23A1.02 (3)C26—C2111.386 (3)
C23—H23B1.00 (2)C26—C271.387 (3)
C22—O221.216 (2)C211—C2101.380 (4)
C22—N211.358 (3)C211—H2110.93 (3)
C22—N221.407 (2)C210—C291.370 (4)
C21—O211.443 (2)C210—H2100.92 (3)
C21—C261.497 (3)C29—C281.370 (4)
C21—H21B0.99 (3)C29—H290.92 (3)
C21—H21A1.07 (3)C28—C271.367 (3)
C228—C2191.374 (3)C28—H280.96 (3)
C228—C2231.382 (3)C27—H270.93 (2)
C223—C2221.383 (4)N11—O111.413 (2)
C223—H2230.98 (3)N11—H11N0.89 (2)
C222—C2211.371 (4)N12—O131.4040 (19)
C222—H2221.00 (3)N13—O151.409 (2)
C221—C2201.357 (3)N13—H13N0.88 (3)
C221—H2210.99 (3)N23—O251.411 (2)
C110—C1111.379 (4)N23—H23N0.90 (3)
C110—H1101.02 (3)N22—O231.4022 (19)
C111—H1110.98 (3)N21—O211.411 (2)
C112—C1131.366 (3)N21—H21N0.90 (2)
O11—C11—C16107.69 (17)C115—C116—C117120.3 (3)
O11—C11—H11A107.3 (13)C115—C116—H116123 (2)
C16—C11—H11A113.6 (12)C117—C116—H116117 (2)
O11—C11—H11B109.9 (13)C116—C117—C112120.7 (3)
C16—C11—H11B114.4 (13)C116—C117—H117125.2 (17)
H11A—C11—H11B103.7 (17)C112—C117—H117114.1 (17)
O12—C12—N11124.23 (18)C119—C118—C123118.8 (2)
O12—C12—N12120.73 (17)C119—C118—C15120.6 (2)
N11—C12—N12114.86 (16)C123—C118—C15120.6 (2)
O13—C13—C112106.98 (16)C118—C119—C120121.1 (2)
O13—C13—H13A108.5 (13)C118—C119—H119120.4 (14)
C112—C13—H13A110.0 (14)C120—C119—H119118.5 (14)
O13—C13—H13B104.8 (15)C121—C120—C119119.9 (3)
C112—C13—H13B109.5 (15)C121—C120—H120120.6 (18)
H13A—C13—H13B117 (2)C119—C120—H120119.5 (18)
O14—C14—N13125.68 (19)C120—C121—C122119.8 (3)
O14—C14—N12121.39 (18)C120—C121—H121116.4 (19)
N13—C14—N12112.74 (18)C122—C121—H121123.7 (19)
O15—C15—C118105.37 (18)C121—C122—C123120.6 (3)
O15—C15—H15A106.3 (14)C121—C122—H122122 (2)
C118—C15—H15A109.6 (14)C123—C122—H122118 (2)
O15—C15—H15B105 (2)C118—C123—C122119.8 (3)
C118—C15—H15B114 (2)C118—C123—H123118.1 (17)
H15A—C15—H15B115 (3)C122—C123—H123122.1 (17)
C17—C16—C111118.9 (2)C221—C220—C219119.8 (2)
C17—C16—C11120.70 (19)C221—C220—H220119.1 (16)
C111—C16—C11120.4 (2)C219—C220—H220121.1 (16)
C18—C17—C16120.5 (2)C228—C219—C220121.5 (2)
C18—C17—H17118.4 (14)C228—C219—H219119.2 (13)
C16—C17—H17121.1 (14)C220—C219—H219119.3 (13)
C19—C18—C17120.0 (3)C213—C212—C217118.5 (2)
C19—C18—H18121.6 (18)C213—C212—C23121.4 (2)
C17—C18—H18118.4 (18)C217—C212—C23120.0 (2)
C110—C19—C18120.3 (3)C216—C217—C212120.3 (3)
C110—C19—H19119 (2)C216—C217—H217121.6 (15)
C18—C19—H19120 (2)C212—C217—H217118.1 (15)
O25—C25—C228105.35 (18)C215—C216—C217120.8 (3)
O25—C25—H25A102.3 (17)C215—C216—H216121 (2)
C228—C25—H25A108.9 (17)C217—C216—H216118 (2)
O25—C25—H25B106.3 (17)C216—C215—C214120.1 (3)
C228—C25—H25B114.2 (17)C216—C215—H215119.0 (17)
H25A—C25—H25B118 (2)C214—C215—H215120.9 (17)
O24—C24—N23125.72 (19)C215—C214—C213119.7 (3)
O24—C24—N22121.11 (18)C215—C214—H214124.4 (18)
N23—C24—N22112.99 (17)C213—C214—H214116.0 (18)
O23—C23—C212106.44 (15)C212—C213—C214120.6 (3)
O23—C23—H23A106.4 (13)C212—C213—H213118.4 (14)
C212—C23—H23A114.1 (14)C214—C213—H213121.0 (14)
O23—C23—H23B107.8 (12)C211—C26—C27118.8 (2)
C212—C23—H23B110.7 (13)C211—C26—C21120.7 (2)
H23A—C23—H23B110.9 (19)C27—C26—C21120.47 (19)
O22—C22—N21124.53 (18)C210—C211—C26120.0 (3)
O22—C22—N22120.67 (18)C210—C211—H211119.1 (17)
N21—C22—N22114.62 (17)C26—C211—H211120.9 (17)
O21—C21—C26107.78 (16)C29—C210—C211120.4 (3)
O21—C21—H21B108.4 (13)C29—C210—H210121.1 (17)
C26—C21—H21B110.5 (13)C211—C210—H210118.5 (17)
O21—C21—H21A109.2 (12)C28—C29—C210119.8 (3)
C26—C21—H21A112.0 (12)C28—C29—H29116.8 (19)
H21B—C21—H21A108.9 (18)C210—C29—H29123 (2)
C219—C228—C223118.2 (2)C27—C28—C29120.5 (3)
C219—C228—C25121.4 (2)C27—C28—H28121.0 (15)
C223—C228—C25120.4 (2)C29—C28—H28118.1 (15)
C228—C223—C222120.2 (2)C28—C27—C26120.5 (2)
C228—C223—H223118.3 (17)C28—C27—H27119.6 (14)
C222—C223—H223121.4 (17)C26—C27—H27119.9 (15)
C221—C222—C223120.5 (3)C12—N11—O11112.36 (15)
C221—C222—H222120.2 (17)C12—N11—H11N119.9 (15)
C223—C222—H222119.4 (17)O11—N11—H11N111.2 (15)
C220—C221—C222119.9 (3)C12—N12—O13115.54 (14)
C220—C221—H221123.6 (18)C12—N12—C14124.77 (16)
C222—C221—H221116.5 (18)O13—N12—C14112.89 (14)
C19—C110—C111120.5 (3)C14—N13—O15113.66 (17)
C19—C110—H110121.1 (16)C14—N13—H13N116.3 (16)
C111—C110—H110118.4 (16)O15—N13—H13N112.9 (16)
C110—C111—C16119.7 (2)C24—N23—O25113.23 (16)
C110—C111—H111121.3 (16)C24—N23—H23N113.0 (16)
C16—C111—H111118.9 (16)O25—N23—H23N114.5 (16)
C113—C112—C117118.0 (2)O23—N22—C22115.61 (15)
C113—C112—C13121.2 (2)O23—N22—C24112.75 (14)
C117—C112—C13120.7 (2)C22—N22—C24124.03 (15)
C112—C113—C114120.8 (3)C22—N21—O21112.63 (16)
C112—C113—H113115.8 (15)C22—N21—H21N118.2 (15)
C114—C113—H113122.4 (15)O21—N21—H21N110.5 (14)
C115—C114—C113120.2 (3)N11—O11—C11111.21 (14)
C115—C114—H114119.8 (19)N12—O13—C13108.79 (13)
C113—C114—H114120 (2)N13—O15—C15109.30 (15)
C114—C115—C116119.9 (3)N23—O25—C25110.38 (15)
C114—C115—H115116 (2)N22—O23—C23108.70 (13)
C116—C115—H115124 (2)N21—O21—C21111.00 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N13—H13N···O120.88 (3)1.92 (3)2.627 (2)136 (2)
N23—H23N···O220.90 (3)1.90 (3)2.650 (2)140 (2)
N11—H11N···O13i0.89 (2)2.75 (3)3.286 (1)119 (1)
N11—H11N···O14i0.89 (2)2.05 (3)2.896 (2)158 (2)
N21—H21N···O24ii0.90 (2)2.06 (3)2.926 (2)160 (2)
N21—H21N···O23ii0.90 (2)2.66 (3)3.275 (2)126 (2)
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z+1.
 

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