 
data_06skc0042p21
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
Glutaric Acid & 4-Methylimidazole
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C9 H14 N2 O4'
_chemical_formula_weight          214.22
 
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   0.0000
 '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   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            Monoclinic
_symmetry_space_group_name_H-M    P21
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z'
 
_cell_length_a                    7.5360(4)
_cell_length_b                    14.2180(8)
_cell_length_c                    9.7160(6)
_cell_angle_alpha                 90.00
_cell_angle_beta                  96.571(3)
_cell_angle_gamma                 90.00
_cell_volume                      1034.20(10)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     2417
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        lath
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.13
_exptl_crystal_size_mid           0.07
_exptl_crystal_size_min           0.03
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.376
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              456
_exptl_absorpt_coefficient_mu     0.109
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9860
_exptl_absorpt_correction_T_max   0.9967
_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             12026
_diffrn_reflns_av_R_equivalents   0.1295
_diffrn_reflns_av_sigmaI/netI     0.1106
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -18
_diffrn_reflns_limit_k_max        17
_diffrn_reflns_limit_l_min        -12
_diffrn_reflns_limit_l_max        11
_diffrn_reflns_theta_min          3.07
_diffrn_reflns_theta_max          27.48
_reflns_number_total              2460
_reflns_number_gt                 1739
_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)+(0.0150P)²+0.3727P] 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_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    -10(10)
_refine_ls_number_reflns          2460
_refine_ls_number_parameters      281
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0980
_refine_ls_R_factor_gt            0.0559
_refine_ls_wR_factor_ref          0.1108
_refine_ls_wR_factor_gt           0.0977
_refine_ls_goodness_of_fit_ref    1.038
_refine_ls_restrained_S_all       1.038
_refine_ls_shift/su_max           0.004
_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 0.1071(5) 0.0859(3) -0.2812(5) 0.0231(9) Uani 1 1 d . . .
C2 C 0.0466(5) 0.1075(3) -0.1425(5) 0.0257(10) Uani 1 1 d . . .
H2A H 0.1336 0.0799 -0.0695 0.031 Uiso 1 1 calc R . .
H2B H -0.0696 0.0762 -0.1370 0.031 Uiso 1 1 calc R . .
C3 C 0.0261(5) 0.2117(3) -0.1111(4) 0.0240(9) Uani 1 1 d . . .
H3A H -0.0646 0.2397 -0.1810 0.029 Uiso 1 1 calc R . .
H3B H 0.1410 0.2442 -0.1175 0.029 Uiso 1 1 calc R . .
C4 C -0.0303(5) 0.2262(3) 0.0330(4) 0.0248(10) Uani 1 1 d . . .
H4A H -0.1498 0.1980 0.0362 0.030 Uiso 1 1 calc R . .
H4B H 0.0546 0.1927 0.1013 0.030 Uiso 1 1 calc R . .
C5 C -0.0371(5) 0.3281(3) 0.0745(4) 0.0249(10) Uani 1 1 d . . .
O1A O 0.1335(4) 0.1489(2) -0.3651(3) 0.0280(7) Uani 1 1 d . . .
O1B O 0.1310(4) -0.0011(2) -0.3064(3) 0.0282(8) Uani 1 1 d . . .
O5A O -0.0847(4) 0.3377(2) 0.1998(3) 0.0334(8) Uani 1 1 d . . .
H5 H -0.0933 0.3951 0.2183 0.07(2) Uiso 1 1 calc R . .
O5B O -0.0021(5) 0.3935(2) 0.0030(4) 0.0367(8) Uani 1 1 d . . .
C22 C 0.2516(6) 0.3639(3) 0.5021(5) 0.0253(10) Uani 1 1 d . . .
H22 H 0.2859 0.3241 0.4311 0.030 Uiso 1 1 calc R . .
C24 C 0.1977(5) 0.4902(3) 0.6222(5) 0.0212(10) Uani 1 1 d . . .
C25 C 0.1551(5) 0.4142(3) 0.6935(5) 0.0252(10) Uani 1 1 d . . .
H25 H 0.1101 0.4142 0.7809 0.030 Uiso 1 1 calc R . .
C26 C 0.1864(5) 0.5929(3) 0.6523(5) 0.0268(10) Uani 1 1 d . . .
H26A H 0.1445 0.6017 0.7432 0.040 Uiso 1 1 calc R . .
H26B H 0.1026 0.6228 0.5810 0.040 Uiso 1 1 calc R . .
H26C H 0.3048 0.6214 0.6523 0.040 Uiso 1 1 calc R . .
N21 N 0.1885(4) 0.3362(3) 0.6168(4) 0.0255(9) Uani 1 1 d . . .
H21 H 0.1708 0.2774 0.6404 0.025(13) Uiso 1 1 calc R . .
N23 N 0.2586(4) 0.4574(3) 0.5034(4) 0.0238(8) Uani 1 1 d . . .
H23 H 0.2963 0.4927 0.4383 0.048(16) Uiso 1 1 calc R . .
C31 C 0.4226(5) 0.2365(3) 0.1580(5) 0.0231(9) Uani 1 1 d . . .
C32 C 0.4540(5) 0.3295(3) 0.0907(4) 0.0205(9) Uani 1 1 d . . .
H32A H 0.3722 0.3348 0.0037 0.025 Uiso 1 1 calc R . .
H32B H 0.5779 0.3311 0.0660 0.025 Uiso 1 1 calc R . .
C33 C 0.4256(5) 0.4134(3) 0.1818(5) 0.0231(9) Uani 1 1 d . . .
H33A H 0.3022 0.4115 0.2074 0.028 Uiso 1 1 calc R . .
H33B H 0.5085 0.4086 0.2683 0.028 Uiso 1 1 calc R . .
C34 C 0.4550(6) 0.5068(3) 0.1134(5) 0.0220(9) Uani 1 1 d . . .
H34A H 0.5770 0.5077 0.0848 0.026 Uiso 1 1 calc R . .
H34B H 0.3694 0.5123 0.0285 0.026 Uiso 1 1 calc R . .
C35 C 0.4335(5) 0.5903(3) 0.2038(5) 0.0234(9) Uani 1 1 d . . .
O31A O 0.4437(4) 0.1611(2) 0.0873(3) 0.0262(7) Uani 1 1 d . . .
O31B O 0.3755(4) 0.2341(2) 0.2753(3) 0.0300(8) Uani 1 1 d . . .
O35A O 0.3868(4) 0.5840(2) 0.3194(3) 0.0305(7) Uani 1 1 d . . .
O35B O 0.4654(4) 0.67408(19) 0.1527(4) 0.0294(8) Uani 1 1 d . . .
H35 H 0.4911 0.6681 0.0712 0.042(15) Uiso 1 1 calc R . .
C42 C 0.7018(5) 0.5483(3) 0.6178(4) 0.0249(10) Uani 1 1 d . . .
H42 H 0.7184 0.6120 0.5928 0.030 Uiso 1 1 calc R . .
C44 C 0.6923(5) 0.3934(3) 0.6114(4) 0.0221(10) Uani 1 1 d . . .
C45 C 0.6367(5) 0.4204(4) 0.7322(5) 0.0257(10) Uani 1 1 d . . .
H45 H 0.5998 0.3804 0.8019 0.031 Uiso 1 1 calc R . .
C46 C 0.7090(6) 0.2986(3) 0.5512(5) 0.0293(11) Uani 1 1 d . . .
H46A H 0.6694 0.2512 0.6142 0.044 Uiso 1 1 calc R . .
H46B H 0.8340 0.2869 0.5377 0.044 Uiso 1 1 calc R . .
H46C H 0.6346 0.2949 0.4617 0.044 Uiso 1 1 calc R . .
N41 N 0.6439(4) 0.5189(3) 0.7354(4) 0.0255(8) Uani 1 1 d . . .
H41 H 0.6153 0.5550 0.8031 0.046(15) Uiso 1 1 calc R . .
N43 N 0.7319(4) 0.4744(2) 0.5426(4) 0.0217(8) Uani 1 1 d . . .
H43 H 0.7714 0.4763 0.4608 0.07(2) 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 O1A 1.243(5) . ?
C1 O1B 1.278(5) . ?
C1 C2 1.503(6) . ?
C2 C3 1.523(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.524(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.506(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 O5B 1.208(5) . ?
C5 O5A 1.315(5) . ?
O5A H5 0.8400 . ?
C22 N21 1.321(5) . ?
C22 N23 1.331(5) . ?
C22 H22 0.9500 . ?
C24 C25 1.342(6) . ?
C24 N23 1.371(5) . ?
C24 C26 1.494(6) . ?
C25 N21 1.375(6) . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
N21 H21 0.8800 . ?
N23 H23 0.8800 . ?
C31 O31B 1.233(5) . ?
C31 O31A 1.293(5) . ?
C31 C32 1.506(6) . ?
C32 C33 1.515(6) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.513(6) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.496(6) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 O35A 1.218(5) . ?
C35 O35B 1.323(5) . ?
O35B H35 0.8400 . ?
C42 N43 1.314(5) . ?
C42 N41 1.336(5) . ?
C42 H42 0.9500 . ?
C44 C45 1.347(6) . ?
C44 N43 1.382(5) . ?
C44 C46 1.481(6) . ?
C45 N41 1.401(6) . ?
C45 H45 0.9500 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
N41 H41 0.8800 . ?
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
O1A C1 O1B 122.4(4) . . ?
O1A C1 C2 121.9(4) . . ?
O1B C1 C2 115.7(4) . . ?
C1 C2 C3 115.3(4) . . ?
C1 C2 H2A 108.5 . . ?
C3 C2 H2A 108.5 . . ?
C1 C2 H2B 108.5 . . ?
C3 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
C2 C3 C4 111.2(4) . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C5 C4 C3 113.5(4) . . ?
C5 C4 H4A 108.9 . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
C3 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
O5B C5 O5A 123.6(4) . . ?
O5B C5 C4 124.8(4) . . ?
O5A C5 C4 111.6(4) . . ?
C5 O5A H5 109.5 . . ?
N21 C22 N23 107.9(4) . . ?
N21 C22 H22 126.1 . . ?
N23 C22 H22 126.1 . . ?
C25 C24 N23 106.5(4) . . ?
C25 C24 C26 131.6(4) . . ?
N23 C24 C26 121.9(4) . . ?
C24 C25 N21 107.5(4) . . ?
C24 C25 H25 126.3 . . ?
N21 C25 H25 126.3 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C22 N21 C25 108.8(4) . . ?
C22 N21 H21 125.6 . . ?
C25 N21 H21 125.6 . . ?
C22 N23 C24 109.4(4) . . ?
C22 N23 H23 125.3 . . ?
C24 N23 H23 125.3 . . ?
O31B C31 O31A 122.3(4) . . ?
O31B C31 C32 120.1(4) . . ?
O31A C31 C32 117.6(3) . . ?
C31 C32 C33 113.4(3) . . ?
C31 C32 H32A 108.9 . . ?
C33 C32 H32A 108.9 . . ?
C31 C32 H32B 108.9 . . ?
C33 C32 H32B 108.9 . . ?
H32A C32 H32B 107.7 . . ?
C34 C33 C32 113.4(3) . . ?
C34 C33 H33A 108.9 . . ?
C32 C33 H33A 108.9 . . ?
C34 C33 H33B 108.9 . . ?
C32 C33 H33B 108.9 . . ?
H33A C33 H33B 107.7 . . ?
C35 C34 C33 114.0(3) . . ?
C35 C34 H34A 108.7 . . ?
C33 C34 H34A 108.7 . . ?
C35 C34 H34B 108.7 . . ?
C33 C34 H34B 108.7 . . ?
H34A C34 H34B 107.6 . . ?
O35A C35 O35B 119.8(4) . . ?
O35A C35 C34 123.0(4) . . ?
O35B C35 C34 117.2(3) . . ?
C35 O35B H35 109.5 . . ?
N43 C42 N41 108.6(4) . . ?
N43 C42 H42 125.7 . . ?
N41 C42 H42 125.7 . . ?
C45 C44 N43 106.9(4) . . ?
C45 C44 C46 130.8(4) . . ?
N43 C44 C46 122.3(4) . . ?
C44 C45 N41 106.8(4) . . ?
C44 C45 H45 126.6 . . ?
N41 C45 H45 126.6 . . ?
C44 C46 H46A 109.5 . . ?
C44 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C44 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C42 N41 C45 108.0(4) . . ?
C42 N41 H41 126.0 . . ?
C45 N41 H41 126.0 . . ?
C42 N43 C44 109.7(3) . . ?
C42 N43 H43 125.2 . . ?
C44 N43 H43 125.2 . . ?
 
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
N23 H23 O35A  0.88 1.91 2.787(5) 170.9 .
O5A H5 O1B  0.84 1.75 2.555(4) 161.3 2
N21 H21 O1A  0.88 1.85 2.704(4) 163.3 1_556
O35B H35 O31A  0.84 1.67 2.511(4) 175.6 2_655
N43 H43 O1B  0.88 1.77 2.646(4) 169.9 2_655
N41 H41 O31A  0.88 1.93 2.784(4) 163.9 2_656
 
_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   -0.235
_refine_diff_density_rms    0.061
