organic compounds
N-(2-Chloroethyl)morpholine-4-carboxamide
aDepartment of Pure and Industrial Chemistry, University of Nigeria, Nsukka, Enugu State, Nigeria, and bDepartment of Chemistry, University of Waikato, Private Bag 3105, Hamilton, New Zealand
*Correspondence e-mail: oguejiofo.ujam@unn.edu.ng
The title compound, C7H13ClN2O2, synthesized by the reaction of 2-chloroethyl isocyanate and morpholine, crystallizes with four molecules in the which have similar conformations and comprise two pairs each related by approximate non-crystallographic inversion centres. Two of them have a modest orientational disorder of the 2-chloroethyl fragments [occupancy ratio of 0.778 (4):0.222 (4)]. In the crystal, molecules are linked by N—H⋯O=C hydrogen bonds, forming three crystallographically different kinds of infinite hydrogen-bonded chains extending along [001].
CCDC reference: 991972
Related literature
For the solution-phase preparation of substituted morpholine derivatives, see: Lainton et al. (2003). For a related thiomorpholine analogue, see: Ujam et al. (2010); Henderson et al. (2006).
Experimental
Crystal data
|
Data collection: SMART (Bruker, 2001); cell SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012).
Supporting information
CCDC reference: 991972
10.1107/S1600536814005832/qk2064sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814005832/qk2064Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814005832/qk2064Isup3.mol
Supporting information file. DOI: 10.1107/S1600536814005832/qk2064Isup4.cml
The title compound, N-(2-chloroethyl) morpholine-4-carboxamide, was prepared as part of an ongoing project investigating the multifunctional alkylation of [Pt2(µ-S)2(PPh3)4] (Ujam et al., 2010). The X-ray ═C hydrogen bonds (N···O = 2.809 (6) – 2.831 (6) Å) to form three crystallographically different kinds of infinite hydrogen bonded chains extending along [001] (Fig. 2), all with criss-cross patterns of molecule orientations when viewed along the chains (Fig. 3).
established the molecular structure and atom connectivity of the title compound C7H13Cl1N2O2 (Fig. 1). There are four independent molecules in the which have the same overall conformation and comprise two pairs each related by approximate non-crystallographic inversion centres. Two of them have a modest orientation disorder of the 2-chloroethyl fragments. The molecules consist of a chair-shaped morpholine ring attached to a planar urea-type N2CO unit. The 2-chloroethyl side chains are oriented approximately perpendicular to the N2CO unit. In the the molecules are linked by N—H···OMorpholine [HN(CH2CH2)2O, 200 mg, 0.002 mmol] was added to a solution of 2-chloroethyl isocyanate [ClCH2CH2NCO, 200 mg, 0.002 mmol] in diethyl ether (30 mL), immediately producing a white precipitate of the product. After stirring for 5 min the product was filtered and washed with ether (20 mL) and dried under vacuum to give ClCH2CH2NHC(O)N(CH2CH2)2O. Crystals suitable for X-ray crystallographic analysis were obtained by vapour diffusion of diethyl ether into a dichloromethane solution.
Crystal data, data collection and structure
details are summarized in the crystallographic data Table. Diffraction images of the calculated from the recorded frame data were consistent with the crystallography reported and did reveal neither commensurate nor incommensurate reflections. All attempts to solve the structure in C2/c were unsuccessful, but it solved readily in Cc. The compound has four independent molecules in the comprising two pairs each related by an apparent inversion centre at x,y,z = 0.43, 0.63, 0.81 for the molecules 1 (Cl1, O1, O2, N1, N2, C1 through C7) and 2 (Cl2, N3, N4, O3, O4, C8 through C14), and at x,y,z = 0.42, 0.88, 0.31 for molecules molecules 3 (Cl3, O5, O6, N5, N6, C15 through C21) and 4 (Cl4, N7, N8, O7, O8, C22 through C28) . The two inversion centres were approximately related by 0 0.25 0.5 which is not a crystallographic relationship in C2/c, so the structure could not be converted to the centrosymmetric cell. was completed in the non-centrosymmetric Cc, and the crystal treated as a racemic twin. Unrestrained led to a large spread in values for chemically equivalent bond parameters, and some unrealistic thermal ellipsoids, no doubt arising from instability associated with the Hence the final restrained the independent molecules to similar geometry using the SAME command of SHELXL, and EADP constraints were applied to equivalent atoms related by Some residual electron density appeared to arise from partial disorder of the ethylene groups of two of the molecules (molecules 2 and 4) over two sites (0.78:0.22), so the C atoms of the minor component were included with fixed isotropic thermal parameters. Otherwise all non-hydrogen atoms were treated anisotropically. H atoms attached to carbon atoms were included in calculated positions [Uiso(H) = 1.2×Uequ(C)], but those attached to the amide N atoms were refined with DFIX constraints and Uiso(H) = 0.03 fixed.Data collection: SMART (Bruker, 2001); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012).Fig. 1. The molecular structure and atom numbering of one of the four independent molecules of the title compound with displacement parameters drawn at the 40% probability level for non-H atoms. | |
Fig. 2. Crystal structure of the compound showing the four different intermolecular N—H···O═C hydrogen bonds (dotted lines) within the three different hydrogen bond chains along [001]. C-bonded H atoms omitted for clarity. | |
Fig. 3. Packing diagram of the title compound viewed along [001], the hydrogen bond chain direction. Symmetry equivalent molecules are colour coded and only Cl atoms were labeled. H atoms omitted for clarity. |
C7H13ClN2O2 | F(000) = 1632 |
Mr = 192.64 | Dx = 1.426 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
a = 10.7393 (8) Å | Cell parameters from 3770 reflections |
b = 33.613 (3) Å | θ = 2–27° |
c = 9.9942 (7) Å | µ = 0.39 mm−1 |
β = 95.704 (5)° | T = 99 K |
V = 3589.9 (5) Å3 | Needle, colourless |
Z = 16 | 0.30 × 0.10 × 0.10 mm |
Siemens SMART CCD diffractometer | 5276 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.082 |
ω scans | θmax = 27.8°, θmin = 1.2° |
Absorption correction: multi-scan (SADABS; Sheldrick 2003) | h = −14→14 |
Tmin = 0.892, Tmax = 0.962 | k = −43→44 |
39446 measured reflections | l = −13→13 |
8451 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.059 | H-atom parameters constrained |
wR(F2) = 0.158 | w = 1/[σ2(Fo2) + (0.0582P)2 + 2.927P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
8451 reflections | Δρmax = 0.56 e Å−3 |
307 parameters | Δρmin = −0.59 e Å−3 |
164 restraints | Absolute structure: Flack (1983), 4226 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.38 (17) |
C7H13ClN2O2 | V = 3589.9 (5) Å3 |
Mr = 192.64 | Z = 16 |
Monoclinic, Cc | Mo Kα radiation |
a = 10.7393 (8) Å | µ = 0.39 mm−1 |
b = 33.613 (3) Å | T = 99 K |
c = 9.9942 (7) Å | 0.30 × 0.10 × 0.10 mm |
β = 95.704 (5)° |
Siemens SMART CCD diffractometer | 8451 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick 2003) | 5276 reflections with I > 2σ(I) |
Tmin = 0.892, Tmax = 0.962 | Rint = 0.082 |
39446 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | H-atom parameters constrained |
wR(F2) = 0.158 | Δρmax = 0.56 e Å−3 |
S = 1.04 | Δρmin = −0.59 e Å−3 |
8451 reflections | Absolute structure: Flack (1983), 4226 Friedel pairs |
307 parameters | Absolute structure parameter: 0.38 (17) |
164 restraints |
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. Refined as a 2-component inversion twin (here a polar twin) with a component ratio of 0.38/0.62. The final refinement restrained the four independent molecules to similar geometry using the SAME command of SHELXL, and EADP constraints were applied to equivalent atom pairs related by pseudosymmetry. Some residual electron density appeared to arise from partial disorder of the ethylene groups of two of the molecules over two sites (0.78:0.22) so the C atoms of the minor component were included with fixed isotropic thermal parameters. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.1793 (6) | 0.69065 (18) | 0.5906 (7) | 0.0257 (6) | |
H1A | 0.2429 | 0.6694 | 0.5886 | 0.031* | |
H1B | 0.1907 | 0.7095 | 0.5168 | 0.031* | |
C2 | 0.0503 (6) | 0.67256 (17) | 0.5692 (6) | 0.0295 (6) | |
H2A | −0.0133 | 0.6940 | 0.5615 | 0.035* | |
H2B | 0.0420 | 0.6572 | 0.4843 | 0.035* | |
C3 | 0.0387 (5) | 0.66860 (16) | 0.8026 (6) | 0.0299 (6) | |
H3A | 0.0211 | 0.6505 | 0.8767 | 0.036* | |
H3B | −0.0244 | 0.6901 | 0.7973 | 0.036* | |
C4 | 0.1672 (5) | 0.68631 (15) | 0.8331 (6) | 0.0245 (6) | |
H4A | 0.1701 | 0.7025 | 0.9161 | 0.029* | |
H4B | 0.2300 | 0.6648 | 0.8478 | 0.029* | |
C5 | 0.2610 (4) | 0.74577 (14) | 0.7460 (5) | 0.0216 (5) | |
C6 | 0.3614 (4) | 0.80530 (13) | 0.6609 (5) | 0.0241 (6) | |
H6A | 0.3323 | 0.8190 | 0.7397 | 0.029* | |
H6B | 0.3423 | 0.8225 | 0.5810 | 0.029* | |
C7 | 0.4988 (4) | 0.79800 (13) | 0.6835 (6) | 0.0317 (7) | |
H7A | 0.5272 | 0.7829 | 0.6070 | 0.038* | |
H7B | 0.5187 | 0.7822 | 0.7666 | 0.038* | |
N1 | 0.1972 (4) | 0.71155 (12) | 0.7195 (5) | 0.0201 (5) | |
N2 | 0.2967 (4) | 0.76644 (11) | 0.6398 (4) | 0.0308 (5) | |
H2C | 0.2820 (5) | 0.7572 (2) | 0.5612 (18) | 0.030* | |
O1 | 0.0284 (3) | 0.64694 (11) | 0.6785 (4) | 0.0297 (4) | |
O2 | 0.2846 (3) | 0.75889 (10) | 0.8630 (4) | 0.0292 (4) | |
Cl1 | 0.57778 (12) | 0.84633 (4) | 0.69906 (14) | 0.0372 (2) | |
C8 | 0.6779 (6) | 0.56216 (18) | 1.0240 (7) | 0.0257 (6) | |
H8A | 0.6654 | 0.5439 | 1.0993 | 0.031* | |
H8B | 0.6127 | 0.5830 | 1.0210 | 0.031* | |
C9 | 0.8058 (6) | 0.58091 (17) | 1.0459 (6) | 0.0295 (6) | |
H9A | 0.8108 | 0.5971 | 1.1291 | 0.035* | |
H9B | 0.8695 | 0.5596 | 1.0592 | 0.035* | |
C10 | 0.8262 (5) | 0.58296 (16) | 0.8153 (6) | 0.0299 (6) | |
H10A | 0.8900 | 0.5616 | 0.8237 | 0.036* | |
H10B | 0.8445 | 0.6005 | 0.7401 | 0.036* | |
C11 | 0.6986 (5) | 0.56463 (15) | 0.7835 (6) | 0.0245 (6) | |
H11A | 0.6352 | 0.5859 | 0.7661 | 0.029* | |
H11B | 0.6979 | 0.5481 | 0.7016 | 0.029* | |
C12 | 0.5946 (4) | 0.50722 (14) | 0.8711 (5) | 0.0216 (5) | |
C13 | 0.4970 (5) | 0.44776 (15) | 0.9575 (6) | 0.0241 (6) | 0.778 (4) |
H13A | 0.5150 | 0.4313 | 1.0393 | 0.029* | |
H13B | 0.5310 | 0.4340 | 0.8815 | 0.029* | |
C14 | 0.3576 (5) | 0.45371 (16) | 0.9277 (7) | 0.0317 (7) | 0.778 (4) |
H14A | 0.3393 | 0.4683 | 0.8420 | 0.038* | |
H14B | 0.3249 | 0.4694 | 1.0004 | 0.038* | |
N3 | 0.6675 (4) | 0.54001 (12) | 0.8967 (5) | 0.0201 (5) | |
N4 | 0.5548 (4) | 0.48731 (11) | 0.9778 (4) | 0.0308 (5) | |
H4C | 0.5635 (4) | 0.4978 (3) | 1.0565 (18) | 0.030* | |
O3 | 0.8346 (3) | 0.60560 (10) | 0.9370 (4) | 0.0297 (4) | |
O4 | 0.5687 (3) | 0.49474 (11) | 0.7551 (4) | 0.0292 (4) | |
Cl2 | 0.28368 (12) | 0.40510 (4) | 0.91603 (15) | 0.0372 (2) | |
C15 | 0.1664 (6) | 0.81124 (18) | 0.0959 (7) | 0.0268 (6) | |
H15A | 0.1830 | 0.7940 | 0.0194 | 0.032* | |
H15B | 0.2269 | 0.8335 | 0.1003 | 0.032* | |
C16 | 0.0353 (6) | 0.82743 (18) | 0.0734 (6) | 0.0317 (6) | |
H16A | 0.0273 | 0.8440 | −0.0089 | 0.038* | |
H16B | −0.0244 | 0.8050 | 0.0592 | 0.038* | |
C17 | 0.0137 (5) | 0.82715 (16) | 0.3030 (6) | 0.0283 (6) | |
H17A | −0.0465 | 0.8048 | 0.2915 | 0.034* | |
H17B | −0.0088 | 0.8437 | 0.3790 | 0.034* | |
C18 | 0.1445 (5) | 0.81076 (16) | 0.3359 (6) | 0.0245 (6) | |
H18A | 0.2035 | 0.8330 | 0.3580 | 0.029* | |
H18B | 0.1461 | 0.7932 | 0.4156 | 0.029* | |
C19 | 0.2757 (4) | 0.76025 (14) | 0.2480 (5) | 0.0220 (5) | |
C20 | 0.4416 (4) | 0.71961 (12) | 0.1643 (5) | 0.0251 (6) | |
H20A | 0.4928 | 0.7283 | 0.2470 | 0.030* | |
H20B | 0.4929 | 0.7226 | 0.0879 | 0.030* | |
C21 | 0.4066 (4) | 0.67709 (12) | 0.1778 (6) | 0.0270 (6) | |
H21A | 0.3554 | 0.6680 | 0.0956 | 0.032* | |
H21B | 0.3571 | 0.6736 | 0.2554 | 0.032* | |
N5 | 0.1841 (4) | 0.78819 (12) | 0.2215 (5) | 0.0199 (4) | |
N6 | 0.3293 (4) | 0.74516 (11) | 0.1419 (4) | 0.0298 (5) | |
H6C | 0.2982 (8) | 0.75040 (16) | 0.0619 (18) | 0.030* | |
O5 | 0.0041 (4) | 0.85058 (10) | 0.1835 (4) | 0.0321 (4) | |
O6 | 0.3081 (3) | 0.74858 (11) | 0.3645 (4) | 0.0281 (4) | |
Cl3 | 0.55040 (11) | 0.64849 (4) | 0.20263 (14) | 0.03441 (18) | |
C22 | 0.6776 (6) | 0.94101 (19) | 0.5227 (7) | 0.0268 (6) | |
H22A | 0.6175 | 0.9186 | 0.5190 | 0.032* | |
H22B | 0.6605 | 0.9586 | 0.5981 | 0.032* | |
C23 | 0.8101 (6) | 0.92532 (18) | 0.5449 (6) | 0.0317 (6) | |
H23A | 0.8690 | 0.9480 | 0.5557 | 0.038* | |
H23B | 0.8199 | 0.9095 | 0.6289 | 0.038* | |
C24 | 0.8292 (5) | 0.92350 (16) | 0.3134 (6) | 0.0283 (6) | |
H24A | 0.8502 | 0.9064 | 0.2382 | 0.034* | |
H24B | 0.8895 | 0.9459 | 0.3216 | 0.034* | |
C25 | 0.6977 (5) | 0.93984 (16) | 0.2819 (6) | 0.0245 (6) | |
H25A | 0.6942 | 0.9568 | 0.2006 | 0.029* | |
H25B | 0.6380 | 0.9176 | 0.2637 | 0.029* | |
C26 | 0.5745 (5) | 0.99248 (14) | 0.3691 (5) | 0.0220 (5) | |
C27 | 0.4059 (5) | 1.03184 (15) | 0.4504 (6) | 0.0251 (6) | 0.778 (4) |
H27A | 0.3535 | 1.0278 | 0.5254 | 0.030* | |
H27B | 0.3574 | 1.0232 | 0.3660 | 0.030* | |
C28 | 0.4398 (5) | 1.07526 (15) | 0.4409 (6) | 0.0270 (6) | 0.778 (4) |
H28A | 0.4897 | 1.0796 | 0.3641 | 0.032* | |
H28B | 0.4900 | 1.0839 | 0.5242 | 0.032* | |
N7 | 0.6630 (4) | 0.96323 (12) | 0.3958 (5) | 0.0199 (4) | |
N8 | 0.5208 (4) | 1.00824 (11) | 0.4736 (4) | 0.0298 (5) | |
H8C | 0.5529 (8) | 1.00457 (14) | 0.5510 (18) | 0.030* | |
O7 | 0.8412 (4) | 0.90094 (10) | 0.4351 (4) | 0.0321 (4) | |
O8 | 0.5435 (3) | 1.00387 (11) | 0.2531 (4) | 0.0281 (4) | |
Cl4 | 0.29550 (11) | 1.10319 (3) | 0.41732 (14) | 0.03441 (18) | |
C13A | 0.421 (2) | 0.4712 (5) | 0.954 (2) | 0.030* | 0.222 (4) |
C14A | 0.442 (2) | 0.4253 (5) | 0.939 (2) | 0.030* | 0.222 (4) |
C27A | 0.4955 (18) | 1.0541 (6) | 0.460 (2) | 0.030* | 0.222 (4) |
C28A | 0.3506 (17) | 1.0513 (6) | 0.427 (2) | 0.030* | 0.222 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0285 (14) | 0.0265 (13) | 0.0224 (14) | −0.0047 (11) | 0.0047 (11) | −0.0045 (11) |
C2 | 0.0326 (15) | 0.0302 (14) | 0.0251 (15) | −0.0090 (12) | 0.0001 (11) | 0.0000 (11) |
C3 | 0.0297 (15) | 0.0330 (13) | 0.0280 (15) | −0.0047 (12) | 0.0074 (12) | 0.0043 (11) |
C4 | 0.0281 (15) | 0.0246 (12) | 0.0203 (13) | −0.0047 (11) | 0.0006 (11) | 0.0037 (10) |
C5 | 0.0194 (12) | 0.0249 (12) | 0.0204 (13) | 0.0015 (10) | 0.0019 (10) | 0.0010 (10) |
C6 | 0.0223 (14) | 0.0251 (14) | 0.0244 (14) | 0.0013 (12) | 0.0005 (11) | 0.0010 (11) |
C7 | 0.0235 (15) | 0.0299 (14) | 0.0420 (18) | 0.0007 (12) | 0.0056 (13) | 0.0004 (13) |
N1 | 0.0217 (12) | 0.0223 (10) | 0.0170 (11) | −0.0050 (9) | 0.0049 (9) | −0.0001 (8) |
N2 | 0.0403 (13) | 0.0351 (12) | 0.0168 (11) | −0.0182 (10) | 0.0019 (9) | −0.0016 (9) |
O1 | 0.0318 (11) | 0.0288 (9) | 0.0282 (11) | −0.0122 (8) | 0.0021 (8) | 0.0027 (8) |
O2 | 0.0414 (11) | 0.0290 (9) | 0.0172 (9) | −0.0094 (8) | 0.0037 (8) | −0.0030 (7) |
Cl1 | 0.0332 (4) | 0.0381 (4) | 0.0398 (4) | −0.0168 (3) | 0.0012 (3) | −0.0013 (3) |
C8 | 0.0285 (14) | 0.0265 (13) | 0.0224 (14) | −0.0047 (11) | 0.0047 (11) | −0.0045 (11) |
C9 | 0.0326 (15) | 0.0302 (14) | 0.0251 (15) | −0.0090 (12) | 0.0001 (11) | 0.0000 (11) |
C10 | 0.0297 (15) | 0.0330 (13) | 0.0280 (15) | −0.0047 (12) | 0.0074 (12) | 0.0043 (11) |
C11 | 0.0281 (15) | 0.0246 (12) | 0.0203 (13) | −0.0047 (11) | 0.0006 (11) | 0.0037 (10) |
C12 | 0.0194 (12) | 0.0249 (12) | 0.0204 (13) | 0.0015 (10) | 0.0019 (10) | 0.0010 (10) |
C13 | 0.0223 (14) | 0.0251 (14) | 0.0244 (14) | 0.0013 (12) | 0.0005 (11) | 0.0010 (11) |
C14 | 0.0235 (15) | 0.0299 (14) | 0.0420 (18) | 0.0007 (12) | 0.0056 (13) | 0.0004 (13) |
N3 | 0.0217 (12) | 0.0223 (10) | 0.0170 (11) | −0.0050 (9) | 0.0049 (9) | −0.0001 (8) |
N4 | 0.0403 (13) | 0.0351 (12) | 0.0168 (11) | −0.0182 (10) | 0.0019 (9) | −0.0016 (9) |
O3 | 0.0318 (11) | 0.0288 (9) | 0.0282 (11) | −0.0122 (8) | 0.0021 (8) | 0.0027 (8) |
O4 | 0.0414 (11) | 0.0290 (9) | 0.0172 (9) | −0.0094 (8) | 0.0037 (8) | −0.0030 (7) |
Cl2 | 0.0332 (4) | 0.0381 (4) | 0.0398 (4) | −0.0168 (3) | 0.0012 (3) | −0.0013 (3) |
C15 | 0.0322 (16) | 0.0287 (13) | 0.0202 (14) | 0.0083 (12) | 0.0063 (11) | 0.0035 (10) |
C16 | 0.0370 (16) | 0.0325 (14) | 0.0244 (15) | 0.0131 (12) | −0.0034 (12) | −0.0021 (11) |
C17 | 0.0247 (14) | 0.0296 (13) | 0.0310 (15) | 0.0063 (11) | 0.0056 (11) | −0.0024 (11) |
C18 | 0.0249 (14) | 0.0261 (12) | 0.0227 (14) | 0.0040 (11) | 0.0042 (11) | −0.0027 (10) |
C19 | 0.0245 (13) | 0.0234 (12) | 0.0185 (13) | −0.0012 (10) | 0.0043 (10) | −0.0012 (10) |
C20 | 0.0209 (15) | 0.0286 (13) | 0.0271 (15) | −0.0016 (12) | 0.0082 (11) | −0.0033 (11) |
C21 | 0.0211 (15) | 0.0274 (14) | 0.0322 (16) | −0.0013 (12) | 0.0005 (12) | −0.0019 (12) |
N5 | 0.0233 (11) | 0.0192 (9) | 0.0175 (11) | 0.0023 (8) | 0.0028 (8) | 0.0001 (8) |
N6 | 0.0396 (13) | 0.0344 (11) | 0.0156 (11) | 0.0191 (10) | 0.0035 (9) | 0.0012 (9) |
O5 | 0.0360 (11) | 0.0303 (9) | 0.0293 (11) | 0.0126 (8) | 0.0001 (8) | −0.0031 (8) |
O6 | 0.0343 (10) | 0.0338 (9) | 0.0163 (9) | 0.0116 (8) | 0.0031 (7) | 0.0021 (7) |
Cl3 | 0.0318 (4) | 0.0353 (3) | 0.0355 (4) | 0.0150 (3) | 0.0002 (3) | −0.0016 (3) |
C22 | 0.0322 (16) | 0.0287 (13) | 0.0202 (14) | 0.0083 (12) | 0.0063 (11) | 0.0035 (10) |
C23 | 0.0370 (16) | 0.0325 (14) | 0.0244 (15) | 0.0131 (12) | −0.0034 (12) | −0.0021 (11) |
C24 | 0.0247 (14) | 0.0296 (13) | 0.0310 (15) | 0.0063 (11) | 0.0056 (11) | −0.0024 (11) |
C25 | 0.0249 (14) | 0.0261 (12) | 0.0227 (14) | 0.0040 (11) | 0.0042 (11) | −0.0027 (10) |
C26 | 0.0245 (13) | 0.0234 (12) | 0.0185 (13) | −0.0012 (10) | 0.0043 (10) | −0.0012 (10) |
C27 | 0.0209 (15) | 0.0286 (13) | 0.0271 (15) | −0.0016 (12) | 0.0082 (11) | −0.0033 (11) |
C28 | 0.0211 (15) | 0.0274 (14) | 0.0322 (16) | −0.0013 (12) | 0.0005 (12) | −0.0019 (12) |
N7 | 0.0233 (11) | 0.0192 (9) | 0.0175 (11) | 0.0023 (8) | 0.0028 (8) | 0.0001 (8) |
N8 | 0.0396 (13) | 0.0344 (11) | 0.0156 (11) | 0.0191 (10) | 0.0035 (9) | 0.0012 (9) |
O7 | 0.0360 (11) | 0.0303 (9) | 0.0293 (11) | 0.0126 (8) | 0.0001 (8) | −0.0031 (8) |
O8 | 0.0343 (10) | 0.0338 (9) | 0.0163 (9) | 0.0116 (8) | 0.0031 (7) | 0.0021 (7) |
Cl4 | 0.0318 (4) | 0.0353 (3) | 0.0355 (4) | 0.0150 (3) | 0.0002 (3) | −0.0016 (3) |
C1—N1 | 1.463 (6) | C15—C16 | 1.506 (7) |
C1—C2 | 1.509 (7) | C16—O5 | 1.415 (6) |
C2—O1 | 1.429 (6) | C17—O5 | 1.426 (6) |
C3—O1 | 1.433 (6) | C17—C18 | 1.514 (6) |
C3—C4 | 1.506 (6) | C18—N5 | 1.470 (6) |
C4—N1 | 1.478 (6) | C19—O6 | 1.244 (6) |
C5—O2 | 1.252 (6) | C19—N6 | 1.354 (6) |
C5—N1 | 1.352 (6) | C19—N5 | 1.367 (6) |
C5—N2 | 1.355 (6) | C20—N6 | 1.480 (5) |
C6—N2 | 1.485 (5) | C20—C21 | 1.487 (5) |
C6—C7 | 1.491 (5) | C21—Cl3 | 1.815 (5) |
C7—Cl1 | 1.832 (4) | C22—N7 | 1.467 (6) |
C8—N3 | 1.469 (6) | C22—C23 | 1.513 (7) |
C8—C9 | 1.507 (7) | C23—O7 | 1.435 (6) |
C9—O3 | 1.427 (6) | C24—O7 | 1.428 (6) |
C10—O3 | 1.430 (6) | C24—C25 | 1.519 (6) |
C10—C11 | 1.507 (6) | C25—N7 | 1.462 (6) |
C11—N3 | 1.466 (6) | C26—O8 | 1.235 (5) |
C12—O4 | 1.239 (6) | C26—N8 | 1.351 (6) |
C12—N3 | 1.362 (6) | C26—N7 | 1.375 (6) |
C12—N4 | 1.362 (6) | C27—N8 | 1.466 (6) |
C13—N4 | 1.473 (6) | C27—C28 | 1.509 (7) |
C13—C14 | 1.510 (7) | C28—Cl4 | 1.807 (5) |
C14—Cl2 | 1.815 (5) | C13A—C14A | 1.568 (16) |
C15—N5 | 1.471 (6) | C27A—C28A | 1.561 (17) |
N1—C1—C2 | 110.9 (5) | N5—C15—C16 | 110.9 (5) |
O1—C2—C1 | 110.7 (5) | O5—C16—C15 | 111.9 (5) |
O1—C3—C4 | 111.5 (5) | O5—C17—C18 | 111.8 (5) |
N1—C4—C3 | 109.7 (5) | N5—C18—C17 | 110.7 (5) |
O2—C5—N1 | 122.3 (5) | O6—C19—N6 | 120.9 (4) |
O2—C5—N2 | 120.3 (4) | O6—C19—N5 | 121.8 (5) |
N1—C5—N2 | 117.4 (5) | N6—C19—N5 | 117.3 (5) |
N2—C6—C7 | 108.6 (4) | N6—C20—C21 | 111.2 (4) |
C6—C7—Cl1 | 108.0 (3) | C20—C21—Cl3 | 107.6 (3) |
C5—N1—C1 | 126.9 (5) | C19—N5—C18 | 117.6 (5) |
C5—N1—C4 | 118.9 (5) | C19—N5—C15 | 123.8 (5) |
C1—N1—C4 | 112.4 (4) | C18—N5—C15 | 111.6 (4) |
C5—N2—C6 | 120.3 (4) | C19—N6—C20 | 120.1 (4) |
C2—O1—C3 | 110.6 (4) | C16—O5—C17 | 110.2 (4) |
N3—C8—C9 | 109.1 (5) | N7—C22—C23 | 108.8 (5) |
O3—C9—C8 | 113.4 (5) | O7—C23—C22 | 112.0 (5) |
O3—C10—C11 | 112.1 (5) | O7—C24—C25 | 111.8 (5) |
N3—C11—C10 | 109.9 (5) | N7—C25—C24 | 109.7 (5) |
O4—C12—N3 | 121.4 (5) | O8—C26—N8 | 120.5 (4) |
O4—C12—N4 | 120.5 (4) | O8—C26—N7 | 121.4 (5) |
N3—C12—N4 | 118.1 (5) | N8—C26—N7 | 118.0 (5) |
N4—C13—C14 | 107.7 (4) | N8—C27—C28 | 109.2 (4) |
C13—C14—Cl2 | 108.2 (4) | C27—C28—Cl4 | 107.5 (4) |
C12—N3—C11 | 118.9 (5) | C26—N7—C25 | 117.3 (5) |
C12—N3—C8 | 124.4 (5) | C26—N7—C22 | 123.0 (5) |
C11—N3—C8 | 112.3 (4) | C25—N7—C22 | 112.7 (4) |
C12—N4—C13 | 119.8 (4) | C26—N8—C27 | 120.5 (4) |
C9—O3—C10 | 109.8 (4) | C24—O7—C23 | 109.9 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2C···O6 | 0.85 | 2.03 | 2.831 (6) | 157 |
N4—H4C···O4i | 0.86 | 2.00 | 2.826 (6) | 162 |
N6—H6C···O2ii | 0.85 | 2.00 | 2.819 (6) | 161 |
N8—H8C···O8iii | 0.82 | 2.05 | 2.809 (6) | 153 |
Symmetry codes: (i) x, −y+1, z+1/2; (ii) x, y, z−1; (iii) x, −y+2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2C···O6 | 0.85 | 2.03 | 2.831 (6) | 156.9 |
N4—H4C···O4i | 0.86 | 2.00 | 2.826 (6) | 162.3 |
N6—H6C···O2ii | 0.85 | 2.00 | 2.819 (6) | 160.7 |
N8—H8C···O8iii | 0.82 | 2.05 | 2.809 (6) | 152.6 |
Symmetry codes: (i) x, −y+1, z+1/2; (ii) x, y, z−1; (iii) x, −y+2, z+1/2. |
Acknowledgements
We thank the Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka, for some financial assistant and Dr Tania Groutso, University of Auckland, for the data collection.
References
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Henderson, W., Chong, S. H. & Andy Hor, T. S. (2006). Inorg. Chim. Acta, 359, 3440–3450. Web of Science CrossRef CAS Google Scholar
Lainton, J. A., Allen, M. C., Burton, M., Cameron, S., Edwards, T. R., Harden, G., Hogg, R., Leung, W., Miller, S., Morrish, J. J., Rooke, S. M. & Wendt, B. (2003). J. Comb. Chem. 5, 400–407. Web of Science CrossRef PubMed CAS Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ujam, O. T., Devoy, S. M., Henderson, W., Nicholson, B. K. & Andy Hor, T. S. (2010). Inorg. Chim. Acta, 363, 3558–3568. Web of Science CSD CrossRef CAS Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.