 
data_2008skc0001
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C16 H20 N5 O8'
_chemical_formula_weight          410.37
 
loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            triclinic
_symmetry_space_group_name_H-M    P-1
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    6.9980(3)
_cell_length_b                    8.3790(3)
_cell_length_c                    9.2500(3)
_cell_angle_alpha                 116.302(2)
_cell_angle_beta                  101.825(2)
_cell_angle_gamma                 91.149(2)
_cell_volume                      472.10(3)
_cell_formula_units_Z             1
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     5405
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.19
_exptl_crystal_size_mid           0.09
_exptl_crystal_size_min           0.07
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.443
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              215
_exptl_absorpt_coefficient_mu     0.117
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9780
_exptl_absorpt_correction_T_max   0.9918
_exptl_absorpt_process_details    'SADABS 2007/2 (Sheldrick, G.M., 2007)' 
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature           120(2)
_diffrn_radiation_wavelength           0.71073
_diffrn_radiation_type                      MoK\a
_diffrn_radiation_source                  'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator    'graphite'
_diffrn_measurement_device_type  
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   '9.091'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             10823
_diffrn_reflns_av_R_equivalents   0.0495
_diffrn_reflns_av_sigmaI/netI     0.0435
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -12
_diffrn_reflns_limit_l_max        12
_diffrn_reflns_theta_min          3.00
_diffrn_reflns_theta_max          27.48
_reflns_number_total              2155
_reflns_number_gt                 1691
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'  
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
 
_refine_special_details
;
 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 > 2σ(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.

 The large carbon and hydrogen atom Ueq(max)/Ueq(min) ratio is due to the 
 highly disordered imidazolium molecule which is rotating around a centre 
 of inversion. Two short contacts are also related to this disorder (O1b..
 N45 and O1b..C35).

 All the hydrogen atoms have been fixed as riding in calculated positions, 
 except for H3b which is shared between two malonate molecules and is 
 located on a special position.
;
 
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
 'calc w=1/[σ²(Fo²)+(0.0430P)²+0.2567P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          2155
_refine_ls_number_parameters      150
_refine_ls_number_restraints      91
_refine_ls_R_factor_all           0.0628
_refine_ls_R_factor_gt            0.0447
_refine_ls_wR_factor_ref          0.1109
_refine_ls_wR_factor_gt           0.1003
_refine_ls_goodness_of_fit_ref    1.036
_refine_ls_restrained_S_all       1.014
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_symmetry_multiplicity
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C33 C 1.550(2) 0.866(2) 0.969(3) 0.030(4) Uiso 0.25 1 d PU A -1
H33 H 1.6032 0.7549 0.9387 0.035 Uiso 0.25 1 calc PR A -1
C35 C 1.4509(16) 1.0943(18) 0.9494(19) 0.008(3) Uiso 0.25 1 d PU A -1
H35 H 1.4286 1.1865 0.9169 0.009 Uiso 0.25 1 calc PR A -1
C31 C 1.4839(19) 1.1166(17) 1.1075(16) 0.011(3) Uiso 0.25 1 d PU A -1
H31 H 1.4621 1.2192 1.2001 0.014 Uiso 0.25 1 calc PR A -1
N32 N 1.5502(13) 0.9743(19) 1.1110(14) 0.006(2) Uiso 0.25 1 d PU A -1
H32 H 1.5887 0.9591 1.2002 0.008 Uiso 0.25 1 calc PR A -1
N34 C 1.455(3) 0.933(3) 0.853(3) 0.024(6) Uiso 0.25 1 d PU A -1
H34 H 1.4081 0.8697 0.7361 0.028 Uiso 0.25 1 calc PR A -1
C43 C 1.5345(15) 0.8369(13) 0.9395(14) 0.007(2) Uiso 0.25 1 d PU B -2
H43 H 1.5549 0.7147 0.9033 0.008 Uiso 0.25 1 calc PR B -2
C44 C 1.456(3) 0.911(2) 0.845(2) 0.015(5) Uiso 0.25 1 d PU B -2
H44 H 1.4306 0.8561 0.7272 0.018 Uiso 0.25 1 calc PR B -2
C41 C 1.506(2) 1.130(2) 1.106(2) 0.021(4) Uiso 0.25 1 d PU B -2
H41 H 1.5195 1.2422 1.2022 0.025 Uiso 0.25 1 calc PR B -2
N42 N 1.5802(17) 0.969(2) 1.0977(17) 0.014(3) Uiso 0.25 1 d PU B -2
H42 H 1.6464 0.9576 1.1838 0.017 Uiso 0.25 1 calc PR B -2
N45 C 1.4128(16) 1.093(2) 0.9511(19) 0.006(2) Uiso 0.25 1 d PU B -2
H45 H 1.3353 1.1668 0.9164 0.007 Uiso 0.25 1 calc PR B -2
C1 C 0.7674(2) 0.76677(19) 1.31730(18) 0.0162(3) Uani 1 1 d U . .
C2 C 0.8881(2) 0.6933(2) 1.42493(19) 0.0197(3) Uani 1 1 d U . .
H2A H 0.9946 0.7876 1.5092 0.024 Uiso 1 1 calc R . .
H2B H 0.9501 0.5911 1.3548 0.024 Uiso 1 1 calc R . .
C3 C 0.7635(2) 0.6310(2) 1.51257(18) 0.0189(3) Uani 1 1 d U . .
C22 C 1.2685(2) 0.7121(2) 1.21217(19) 0.0188(3) Uani 1 1 d U . .
H22 H 1.3462 0.6561 1.2689 0.023 Uiso 1 1 calc R . .
C24 C 1.0995(2) 0.9070(2) 1.16015(19) 0.0212(3) Uani 1 1 d U . .
H24 H 1.0393 1.0122 1.1759 0.025 Uiso 1 1 calc R . .
C25 C 1.0938(2) 0.7631(2) 1.01333(19) 0.0205(3) Uani 1 1 d U . .
H25 H 1.0287 0.7476 0.9063 0.025 Uiso 1 1 calc R . .
N21 N 1.20081(19) 0.64314(17) 1.04887(15) 0.0188(3) Uani 1 1 d U . .
H21 H 1.2210 0.5378 0.9752 0.023 Uiso 1 1 calc R . .
N23 N 1.2090(2) 0.87275(17) 1.28276(15) 0.0189(3) Uani 1 1 d U . .
H23 H 1.2353 0.9452 1.3901 0.023 Uiso 1 1 calc R . .
O1A O 0.72206(17) 0.92382(14) 1.38825(13) 0.0221(3) Uani 1 1 d U . .
O1B O 0.71558(17) 0.67148(14) 1.16263(13) 0.0228(3) Uani 1 1 d U . .
O3A O 0.83445(18) 0.64737(16) 1.65188(13) 0.0272(3) Uani 1 1 d U . .
O3B O 0.58686(18) 0.55872(17) 1.42737(14) 0.0292(3) Uani 1 1 d U . .
H3B H 0.5000 0.5000 1.5000 0.099(15) Uiso 1 2 d S . .
 
loop_
 _atom_site_aniso_label
 _atom_site_aniso_U_11
 _atom_site_aniso_U_22
 _atom_site_aniso_U_33
 _atom_site_aniso_U_23
 _atom_site_aniso_U_13
 _atom_site_aniso_U_12
C1 0.0173(7) 0.0164(7) 0.0160(7) 0.0080(6) 0.0045(6) 0.0015(6)
C2 0.0190(8) 0.0221(8) 0.0186(7) 0.0107(6) 0.0018(6) 0.0043(6)
C3 0.0249(8) 0.0154(7) 0.0160(7) 0.0080(6) 0.0019(6) 0.0047(6)
C22 0.0187(8) 0.0194(8) 0.0182(7) 0.0087(6) 0.0041(6) 0.0023(6)
C24 0.0234(8) 0.0206(8) 0.0194(8) 0.0097(6) 0.0031(6) 0.0054(6)
C25 0.0223(8) 0.0217(8) 0.0177(7) 0.0104(6) 0.0015(6) 0.0035(6)
N21 0.0221(7) 0.0164(6) 0.0143(6) 0.0043(5) 0.0035(5) 0.0034(5)
N23 0.0225(7) 0.0179(6) 0.0131(6) 0.0047(5) 0.0030(5) 0.0027(5)
O1A 0.0300(6) 0.0172(5) 0.0163(5) 0.0057(4) 0.0043(5) 0.0062(5)
O1B 0.0315(7) 0.0202(6) 0.0138(5) 0.0061(4) 0.0032(5) 0.0066(5)
O3A 0.0321(7) 0.0320(7) 0.0158(6) 0.0125(5) -0.0015(5) 0.0007(5)
O3B 0.0264(6) 0.0398(7) 0.0239(6) 0.0219(6) -0.0044(5) -0.0097(5)
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C33 N32 1.22(2) . ?
C33 N34 1.47(3) . ?
C33 H33 0.9500 . ?
C35 N34 1.25(3) . ?
C35 C31 1.358(17) . ?
C35 H35 0.9500 . ?
C31 N32 1.299(18) . ?
C31 H31 0.9500 . ?
N32 H32 0.8800 . ?
N34 H34 0.9500 . ?
C43 C44 1.32(2) . ?
C43 N42 1.352(19) . ?
C43 H43 0.9500 . ?
C44 N45 1.48(2) . ?
C44 H44 0.9500 . ?
C41 N45 1.333(19) . ?
C41 N42 1.44(2) . ?
C41 H41 0.9500 . ?
N42 H42 0.8800 . ?
N45 H45 0.9500 . ?
C1 O1B 1.2567(18) . ?
C1 O1A 1.2649(18) . ?
C1 C2 1.517(2) . ?
C2 C3 1.529(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O3A 1.2263(18) . ?
C3 O3B 1.290(2) . ?
C22 N21 1.328(2) . ?
C22 N23 1.329(2) . ?
C22 H22 0.9500 . ?
C24 C25 1.351(2) . ?
C24 N23 1.377(2) . ?
C24 H24 0.9500 . ?
C25 N21 1.379(2) . ?
C25 H25 0.9500 . ?
N21 H21 0.8800 . ?
N23 H23 0.8800 . ?
O3B H3B 1.2293(11) . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
N32 C33 N34 109.3(15) . . ?
N32 C33 H33 125.3 . . ?
N34 C33 H33 125.3 . . ?
N34 C35 C31 109.0(12) . . ?
N34 C35 H35 125.5 . . ?
C31 C35 H35 125.5 . . ?
N32 C31 C35 108.7(10) . . ?
N32 C31 H31 125.7 . . ?
C35 C31 H31 125.7 . . ?
C33 N32 C31 108.3(11) . . ?
C33 N32 H32 125.8 . . ?
C31 N32 H32 125.8 . . ?
C35 N34 C33 102.0(19) . . ?
C35 N34 H34 129.0 . . ?
C33 N34 H34 129.0 . . ?
C44 C43 N42 106.6(13) . . ?
C44 C43 H43 126.7 . . ?
N42 C43 H43 126.7 . . ?
C43 C44 N45 109.4(16) . . ?
C43 C44 H44 125.3 . . ?
N45 C44 H44 125.3 . . ?
N45 C41 N42 106.5(11) . . ?
N45 C41 H41 126.8 . . ?
N42 C41 H41 126.8 . . ?
C43 N42 C41 110.5(9) . . ?
C43 N42 H42 124.8 . . ?
C41 N42 H42 124.8 . . ?
C41 N45 C44 105.6(11) . . ?
C41 N45 H45 127.2 . . ?
C44 N45 H45 127.2 . . ?
O1B C1 O1A 122.23(14) . . ?
O1B C1 C2 119.77(13) . . ?
O1A C1 C2 118.00(13) . . ?
C1 C2 C3 112.29(13) . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C3 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?
O3A C3 O3B 124.79(15) . . ?
O3A C3 C2 120.26(14) . . ?
O3B C3 C2 114.93(13) . . ?
N21 C22 N23 108.37(14) . . ?
N21 C22 H22 125.8 . . ?
N23 C22 H22 125.8 . . ?
C25 C24 N23 107.22(14) . . ?
C25 C24 H24 126.4 . . ?
N23 C24 H24 126.4 . . ?
C24 C25 N21 106.68(13) . . ?
C24 C25 H25 126.7 . . ?
N21 C25 H25 126.7 . . ?
C22 N21 C25 109.02(13) . . ?
C22 N21 H21 125.5 . . ?
C25 N21 H21 125.5 . . ?
C22 N23 C24 108.71(13) . . ?
C22 N23 H23 125.6 . . ?
C24 N23 H23 125.6 . . ?
C3 O3B H3B 111.48(11) . . ?
 
loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_angle_DHA
 _geom_hbond_site_symmetry_A
N32 H32 O1A  0.88 1.95 2.815(8) 169.2 1_655
N32 H32 O1B  0.88 2.49 2.995(11) 117.4 1_655
N42 H42 O1A  0.88 2.00 2.859(10) 164.1 1_655
N42 H42 O1B  0.88 2.39 2.942(14) 121.5 1_655
N21 H21 O1B  0.88 1.78 2.6607(17) 174.7 2_767
N23 H23 O1A  0.88 1.80 2.6772(16) 174.5 2_778
O3B H3B O3B  1.2293(11) 1.2293(11) 2.459(2) 180.000(1) 2_668
O3B H3B O3A  1.2293(11) 2.4445(12) 3.1623(17) 114.72(6) 2_668
 
_diffrn_measured_fraction_theta_max    0.998
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    0.269
_refine_diff_density_min   -0.263
_refine_diff_density_rms    0.056
