 
data_06skc0047p-1
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
Glutaric Acid and 1-Methylimidazole
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C18 H28 N4 O8'
_chemical_formula_weight          428.44
 
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                    8.1285(6)
_cell_length_b                    9.1297(7)
_cell_length_c                    13.7387(11)
_cell_angle_alpha                 89.781(4)
_cell_angle_beta                  89.170(4)
_cell_angle_gamma                 79.782(5)
_cell_volume                      1003.28(13)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     4427
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        lath
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.10
_exptl_crystal_size_mid           0.06
_exptl_crystal_size_min           0.04
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.418
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              456
_exptl_absorpt_coefficient_mu     0.112
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9889
_exptl_absorpt_correction_T_max   0.9955
_exptl_absorpt_process_details       'SADABS V2.10 (Sheldrick, G.M., 2003)' 
 
_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    '10cm confocal mirrors'
_diffrn_measurement_device_type  'Bruker-Nonius 95mm 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             18747
_diffrn_reflns_av_R_equivalents   0.1239
_diffrn_reflns_av_sigmaI/netI     0.1191
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_theta_min          2.93
_diffrn_reflns_theta_max          27.48
_reflns_number_total              4591
_reflns_number_gt                 2970
_reflns_threshold_expression      >2sigma(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, 1997)'
_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 > 2sigma(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.
;
 
_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)+(0.0695P)²+9.7604P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          4591
_refine_ls_number_parameters      276
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1929
_refine_ls_R_factor_gt            0.1381
_refine_ls_wR_factor_ref          0.3389
_refine_ls_wR_factor_gt           0.3124
_refine_ls_goodness_of_fit_ref    1.094
_refine_ls_restrained_S_all       1.094
_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
C1 C 0.6784(8) 0.5554(7) 0.8046(5) 0.0265(14) Uani 1 1 d . . .
C2 C 0.6000(9) 0.6308(8) 0.7142(5) 0.0280(15) Uani 1 1 d . . .
H2A H 0.6002 0.7388 0.7197 0.034 Uiso 1 1 calc R . .
H2B H 0.4818 0.6175 0.7128 0.034 Uiso 1 1 calc R . .
C3 C 0.6822(8) 0.5774(6) 0.6175(4) 0.0209(13) Uani 1 1 d . . .
H3A H 0.6761 0.4711 0.6080 0.025 Uiso 1 1 calc R . .
H3B H 0.8015 0.5874 0.6177 0.025 Uiso 1 1 calc R . .
C4 C 0.5928(8) 0.6702(7) 0.5345(5) 0.0254(14) Uani 1 1 d . . .
H4A H 0.4716 0.6680 0.5397 0.030 Uiso 1 1 calc R . .
H4B H 0.6075 0.7748 0.5423 0.030 Uiso 1 1 calc R . .
C5 C 0.6548(8) 0.6170(7) 0.4339(5) 0.0243(14) Uani 1 1 d . . .
O1A O 0.6099(6) 0.6093(6) 0.8883(3) 0.0320(11) Uani 1 1 d . . .
H1 H 0.5352 0.6834 0.8773 0.048 Uiso 1 1 calc R . .
O1B O 0.7903(6) 0.4494(5) 0.8013(3) 0.0275(11) Uani 1 1 d . . .
O5A O 0.7656(6) 0.5034(5) 0.4208(3) 0.0300(11) Uani 1 1 d . . .
O5B O 0.5864(6) 0.6909(5) 0.3604(3) 0.0304(11) Uani 1 1 d . . .
H5 H 0.5195 0.7660 0.3802 0.046 Uiso 1 1 calc R . .
C22 C 1.0484(8) 0.1865(7) 0.6958(5) 0.0253(14) Uani 1 1 d . . .
H22 H 0.9759 0.2656 0.7275 0.030 Uiso 1 1 calc R . .
C24 C 1.2376(9) -0.0153(9) 0.6689(6) 0.0364(17) Uani 1 1 d . . .
H24 H 1.3198 -0.1013 0.6799 0.044 Uiso 1 1 calc R . .
C25 C 1.1842(9) 0.0390(8) 0.5856(6) 0.0348(17) Uani 1 1 d . . .
H25 H 1.2223 -0.0031 0.5244 0.042 Uiso 1 1 calc R . .
C26 C 0.9732(9) 0.2579(8) 0.5252(6) 0.0394(19) Uani 1 1 d . . .
H26A H 0.8536 0.2570 0.5343 0.059 Uiso 1 1 calc R . .
H26B H 1.0090 0.2203 0.4601 0.059 Uiso 1 1 calc R . .
H26C H 0.9938 0.3599 0.5319 0.059 Uiso 1 1 calc R . .
N21 N 1.0654(7) 0.1654(6) 0.5969(4) 0.0287(13) Uani 1 1 d . . .
N23 N 1.1500(8) 0.0781(7) 0.7390(5) 0.0352(14) Uani 1 1 d . . .
H23 H 1.1607 0.0665 0.8023 0.04(2) Uiso 1 1 calc R . .
C31 C 0.3173(7) 0.9124(7) 0.9332(4) 0.0196(13) Uani 1 1 d . . .
C32 C 0.3760(8) 0.8604(7) 1.0349(4) 0.0231(13) Uani 1 1 d . . .
H32A H 0.3598 0.7561 1.0429 0.028 Uiso 1 1 calc R . .
H32B H 0.4977 0.8603 1.0379 0.028 Uiso 1 1 calc R . .
C33 C 0.2930(8) 0.9488(6) 1.1207(4) 0.0192(12) Uani 1 1 d . . .
H33A H 0.1721 0.9447 1.1218 0.023 Uiso 1 1 calc R . .
H33B H 0.3053 1.0542 1.1134 0.023 Uiso 1 1 calc R . .
C34 C 0.3700(8) 0.8878(7) 1.2159(4) 0.0210(13) Uani 1 1 d . . .
H34A H 0.3600 0.7815 1.2205 0.025 Uiso 1 1 calc R . .
H34B H 0.4907 0.8924 1.2131 0.025 Uiso 1 1 calc R . .
C35 C 0.2971(8) 0.9644(7) 1.3077(4) 0.0242(14) Uani 1 1 d . . .
O31A O 0.3821(6) 0.8307(5) 0.8628(3) 0.0284(11) Uani 1 1 d . . .
O31B O 0.2128(6) 1.0272(5) 0.9252(3) 0.0299(11) Uani 1 1 d . . .
O35A O 0.3587(6) 0.9071(5) 1.3873(3) 0.0301(11) Uani 1 1 d . . .
O35B O 0.1834(6) 1.0766(5) 1.3064(3) 0.0275(11) Uani 1 1 d . . .
C42 C -0.1007(8) 1.3763(8) 1.2078(5) 0.0277(15) Uani 1 1 d . . .
H42 H -0.1231 1.4029 1.2741 0.033 Uiso 1 1 calc R . .
C44 C -0.0012(9) 1.2558(8) 1.0728(5) 0.0328(16) Uani 1 1 d . . .
H44 H 0.0584 1.1832 1.0298 0.039 Uiso 1 1 calc R . .
C45 C -0.1061(9) 1.3793(8) 1.0505(6) 0.0344(17) Uani 1 1 d . . .
H45 H -0.1338 1.4109 0.9859 0.041 Uiso 1 1 calc R . .
C46 C -0.2866(10) 1.5959(9) 1.1343(6) 0.0422(19) Uani 1 1 d . . .
H46A H -0.2328 1.6757 1.1078 0.063 Uiso 1 1 calc R . .
H46B H -0.3208 1.6186 1.2021 0.063 Uiso 1 1 calc R . .
H46C H -0.3852 1.5880 1.0958 0.063 Uiso 1 1 calc R . .
N41 N -0.1677(7) 1.4536(6) 1.1302(4) 0.0316(13) Uani 1 1 d . . .
N43 N 0.0012(7) 1.2576(6) 1.1760(4) 0.0307(13) Uani 1 1 d . . .
H43 H 0.0614 1.1900 1.2129 0.037 Uiso 1 1 calc R . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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
C1 O1B 1.205(8) . ?
C1 O1A 1.327(8) . ?
C1 C2 1.512(9) . ?
C2 C3 1.520(9) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.531(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.516(9) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 O5A 1.258(8) . ?
C5 O5B 1.289(8) . ?
O1A H1 0.8400 . ?
O5B H5 0.8400 . ?
C22 N23 1.317(9) . ?
C22 N21 1.374(9) . ?
C22 H22 0.9500 . ?
C24 C25 1.296(11) . ?
C24 N23 1.390(10) . ?
C24 H24 0.9500 . ?
C25 N21 1.374(9) . ?
C25 H25 0.9500 . ?
C26 N21 1.427(9) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
N23 H23 0.8800 . ?
C31 O31B 1.232(8) . ?
C31 O31A 1.273(7) . ?
C31 C32 1.529(8) . ?
C32 C33 1.512(8) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.519(8) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.506(9) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 O35B 1.252(8) . ?
C35 O35A 1.281(8) . ?
C42 N43 1.314(9) . ?
C42 N41 1.344(8) . ?
C42 H42 0.9500 . ?
C44 C45 1.325(10) . ?
C44 N43 1.419(9) . ?
C44 H44 0.9500 . ?
C45 N41 1.333(9) . ?
C45 H45 0.9500 . ?
C46 N41 1.477(9) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
N43 H43 0.8800 . ?
 
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
O1B C1 O1A 122.1(6) . . ?
O1B C1 C2 122.5(6) . . ?
O1A C1 C2 115.3(5) . . ?
C1 C2 C3 116.5(5) . . ?
C1 C2 H2A 108.2 . . ?
C3 C2 H2A 108.2 . . ?
C1 C2 H2B 108.2 . . ?
C3 C2 H2B 108.2 . . ?
H2A C2 H2B 107.3 . . ?
C2 C3 C4 109.6(5) . . ?
C2 C3 H3A 109.8 . . ?
C4 C3 H3A 109.8 . . ?
C2 C3 H3B 109.8 . . ?
C4 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
C5 C4 C3 113.9(5) . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
O5A C5 O5B 120.2(6) . . ?
O5A C5 C4 122.4(6) . . ?
O5B C5 C4 117.4(5) . . ?
C1 O1A H1 109.5 . . ?
C5 O5B H5 109.5 . . ?
N23 C22 N21 108.2(6) . . ?
N23 C22 H22 125.9 . . ?
N21 C22 H22 125.9 . . ?
C25 C24 N23 106.0(7) . . ?
C25 C24 H24 127.0 . . ?
N23 C24 H24 127.0 . . ?
C24 C25 N21 111.3(7) . . ?
C24 C25 H25 124.3 . . ?
N21 C25 H25 124.3 . . ?
N21 C26 H26A 109.5 . . ?
N21 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N21 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C22 N21 C25 105.2(6) . . ?
C22 N21 C26 125.1(6) . . ?
C25 N21 C26 129.8(7) . . ?
C22 N23 C24 109.3(6) . . ?
C22 N23 H23 125.3 . . ?
C24 N23 H23 125.3 . . ?
O31B C31 O31A 125.3(6) . . ?
O31B C31 C32 118.8(5) . . ?
O31A C31 C32 115.9(5) . . ?
C33 C32 C31 117.4(5) . . ?
C33 C32 H32A 108.0 . . ?
C31 C32 H32A 108.0 . . ?
C33 C32 H32B 108.0 . . ?
C31 C32 H32B 108.0 . . ?
H32A C32 H32B 107.2 . . ?
C32 C33 C34 111.1(5) . . ?
C32 C33 H33A 109.4 . . ?
C34 C33 H33A 109.4 . . ?
C32 C33 H33B 109.4 . . ?
C34 C33 H33B 109.4 . . ?
H33A C33 H33B 108.0 . . ?
C35 C34 C33 116.7(5) . . ?
C35 C34 H34A 108.1 . . ?
C33 C34 H34A 108.1 . . ?
C35 C34 H34B 108.1 . . ?
C33 C34 H34B 108.1 . . ?
H34A C34 H34B 107.3 . . ?
O35B C35 O35A 122.1(6) . . ?
O35B C35 C34 122.2(5) . . ?
O35A C35 C34 115.6(6) . . ?
N43 C42 N41 108.0(6) . . ?
N43 C42 H42 126.0 . . ?
N41 C42 H42 126.0 . . ?
C45 C44 N43 103.6(7) . . ?
C45 C44 H44 128.2 . . ?
N43 C44 H44 128.2 . . ?
C44 C45 N41 111.5(7) . . ?
C44 C45 H45 124.3 . . ?
N41 C45 H45 124.3 . . ?
N41 C46 H46A 109.5 . . ?
N41 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
N41 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C45 N41 C42 107.7(6) . . ?
C45 N41 C46 127.1(6) . . ?
C42 N41 C46 125.2(6) . . ?
C42 N43 C44 109.2(6) . . ?
C42 N43 H43 125.4 . . ?
C44 N43 H43 125.4 . . ?
 
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
O1A H1 O31A  0.84 1.68 2.515(7) 176.3 .
N43 H43 O35B  0.88 1.84 2.705(7) 169.4 .
N23 H23 O31B  0.88 1.77 2.640(8) 171.2 1_645
O5B H5 O35A  0.84 1.67 2.480(6) 162.3 1_554
 
_diffrn_measured_fraction_theta_max    0.996
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.996
_refine_diff_density_max    1.166
_refine_diff_density_min   -0.615
_refine_diff_density_rms    0.120
