 
data_ssf1337
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
Adipic Acid and 2-Methylimidazole
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C10 H18 N2 O5'
_chemical_formula_weight          246.26
 
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                    4.8629(3)
_cell_length_b                    7.9978(5)
_cell_length_c                    16.5263(11)
_cell_angle_alpha                 96.9510(10)
_cell_angle_beta                  94.4750(10)
_cell_angle_gamma                 107.3840(10)
_cell_volume                      604.44(7)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     3399
_cell_measurement_theta_min       2.96
_cell_measurement_theta_max       28.64
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.08
_exptl_crystal_size_mid           0.06
_exptl_crystal_size_min           0.06
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.353
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              264
_exptl_absorpt_coefficient_mu     0.109
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   0.9914
_exptl_absorpt_correction_T_max   0.9935
_exptl_absorpt_process_details    ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.67100
_diffrn_radiation_type            synchrotron
_diffrn_radiation_source          'Daresbury SRS station 9.8'
_diffrn_radiation_monochromator   'silicon 111'
_diffrn_measurement_device_type   'Bruker SMART APEX2 CCD diffractometer'
_diffrn_measurement_method        'fine-slice ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          0
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         5
_diffrn_reflns_number             5294
_diffrn_reflns_av_R_equivalents   0.0347
_diffrn_reflns_av_sigmaI/netI     0.0475
_diffrn_reflns_limit_h_min        -6
_diffrn_reflns_limit_h_max        6
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -21
_diffrn_reflns_limit_l_max        21
_diffrn_reflns_theta_min          2.97
_diffrn_reflns_theta_max          25.83
_reflns_number_total              2668
_reflns_number_gt                 2332
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        'Bruker APEX2'
_computing_cell_refinement        'Bruker SAINT'
_computing_data_reduction         'Bruker SAINT'
_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)+(0.0943P)²+0.1565P] 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          2668
_refine_ls_number_parameters      167
_refine_ls_number_restraints      3
_refine_ls_R_factor_all           0.0573
_refine_ls_R_factor_gt            0.0516
_refine_ls_wR_factor_ref          0.1504
_refine_ls_wR_factor_gt           0.1437
_refine_ls_goodness_of_fit_ref    1.051
_refine_ls_restrained_S_all       1.051
_refine_ls_shift/su_max           0.060
_refine_ls_shift/su_mean          0.003
 
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 0.7807(3) 0.40566(17) 0.33759(8) 0.0163(3) Uani 1 1 d . . .
C2 C 0.6429(3) 0.51297(18) 0.39389(8) 0.0185(3) Uani 1 1 d . . .
H2A H 0.4645 0.5201 0.3633 0.022 Uiso 1 1 calc R . .
H2B H 0.7785 0.6351 0.4084 0.022 Uiso 1 1 calc R . .
C3 C 0.5643(3) 0.44049(17) 0.47294(8) 0.0171(3) Uani 1 1 d . . .
H3A H 0.7404 0.4306 0.5037 0.021 Uiso 1 1 calc R . .
H3B H 0.4220 0.3202 0.4593 0.021 Uiso 1 1 calc R . .
O1A O 0.8634(2) 0.28436(13) 0.36148(6) 0.0204(3) Uani 1 1 d . . .
O1B O 0.8110(2) 0.44534(14) 0.26538(6) 0.0236(3) Uani 1 1 d . . .
C22 C 0.7541(3) 0.98177(18) -0.23851(8) 0.0190(3) Uani 1 1 d . . .
C24 C 0.8726(3) 0.79678(19) -0.16389(9) 0.0224(3) Uani 1 1 d . . .
H24 H 0.9491 0.7078 -0.1480 0.027 Uiso 1 1 calc R . .
C25 C 0.7328(3) 0.88782(18) -0.11766(9) 0.0211(3) Uani 1 1 d . . .
H25 H 0.6922 0.8757 -0.0630 0.025 Uiso 1 1 calc R . .
C26 C 0.7221(3) 1.0795(2) -0.30716(9) 0.0264(3) Uani 1 1 d . . .
H26A H 0.8656 1.0714 -0.3447 0.040 Uiso 1 1 calc R . .
H26B H 0.7533 1.2042 -0.2855 0.040 Uiso 1 1 calc R . .
H26C H 0.5264 1.0278 -0.3368 0.040 Uiso 1 1 calc R . .
N21 N 0.6602(3) 1.00224(15) -0.16544(7) 0.0191(3) Uani 1 1 d . . .
H21 H 0.5665 1.0770 -0.1500 0.041(6) Uiso 1 1 calc R . .
N23 N 0.8838(3) 0.85707(16) -0.23861(7) 0.0206(3) Uani 1 1 d . . .
H23 H 0.9641 0.8190 -0.2799 0.065(8) Uiso 1 1 calc R . .
C31 C 0.6964(3) 0.68076(17) 0.13572(8) 0.0153(3) Uani 1 1 d . . .
C32 C 0.8588(3) 0.55865(17) 0.10178(7) 0.0152(3) Uani 1 1 d . . .
H32A H 0.7406 0.4350 0.1037 0.018 Uiso 1 1 calc R . .
H32B H 1.0416 0.5832 0.1385 0.018 Uiso 1 1 calc R . .
C33 C 0.9331(3) 0.57167(17) 0.01500(8) 0.0153(3) Uani 1 1 d . . .
H33A H 1.0719 0.6901 0.0133 0.018 Uiso 1 1 calc R . .
H33B H 0.7550 0.5581 -0.0220 0.018 Uiso 1 1 calc R . .
O31A O 0.6259(2) 0.66787(14) 0.20949(6) 0.0218(3) Uani 1 1 d . . .
H31 H 0.6982 0.5969 0.2298 0.086(10) Uiso 1 1 calc R . .
O31B O 0.6304(2) 0.78562(13) 0.09504(6) 0.0189(3) Uani 1 1 d . . .
O1W O 0.7898(3) 0.0793(2) 0.49130(8) 0.0402(4) Uani 1 1 d D . .
H1W H 0.825(11) -0.010(4) 0.473(3) 0.19(2) Uiso 1 1 d D . .
H2W H 0.809(5) 0.151(3) 0.4574(13) 0.048(6) Uiso 1 1 d D . .
 
 
_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 1.2491(16) . ?
C1 O1B 1.2797(16) . ?
C1 C2 1.5162(18) . ?
C2 C3 1.5224(17) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C3 1.528(2) 2_666 ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C22 N23 1.3297(17) . ?
C22 N21 1.3328(18) . ?
C22 C26 1.477(2) . ?
C24 C25 1.349(2) . ?
C24 N23 1.3781(19) . ?
C24 H24 0.9500 . ?
C25 N21 1.3820(18) . ?
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 1.2337(16) . ?
C31 O31A 1.2994(15) . ?
C31 C32 1.5132(17) . ?
C32 C33 1.5142(17) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C33 1.530(2) 2_765 ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
O31A H31 0.8400 . ?
O1W H1W 0.814(18) . ?
O1W H2W 0.839(15) . ?
 
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 121.60(12) . . ?
O1A C1 C2 120.90(11) . . ?
O1B C1 C2 117.50(12) . . ?
C1 C2 C3 115.17(11) . . ?
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 C3 111.66(13) . 2_666 ?
C2 C3 H3A 109.3 . . ?
C3 C3 H3A 109.3 2_666 . ?
C2 C3 H3B 109.3 . . ?
C3 C3 H3B 109.3 2_666 . ?
H3A C3 H3B 107.9 . . ?
N23 C22 N21 107.53(12) . . ?
N23 C22 C26 125.85(13) . . ?
N21 C22 C26 126.62(13) . . ?
C25 C24 N23 107.14(13) . . ?
C25 C24 H24 126.4 . . ?
N23 C24 H24 126.4 . . ?
C24 C25 N21 106.51(12) . . ?
C24 C25 H25 126.7 . . ?
N21 C25 H25 126.7 . . ?
C22 C26 H26A 109.5 . . ?
C22 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C22 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C22 N21 C25 109.46(12) . . ?
C22 N21 H21 125.3 . . ?
C25 N21 H21 125.3 . . ?
C22 N23 C24 109.36(12) . . ?
C22 N23 H23 125.3 . . ?
C24 N23 H23 125.3 . . ?
O31B C31 O31A 121.60(12) . . ?
O31B C31 C32 121.74(11) . . ?
O31A C31 C32 116.66(11) . . ?
C31 C32 C33 116.18(10) . . ?
C31 C32 H32A 108.2 . . ?
C33 C32 H32A 108.2 . . ?
C31 C32 H32B 108.2 . . ?
C33 C32 H32B 108.2 . . ?
H32A C32 H32B 107.4 . . ?
C32 C33 C33 110.84(13) . 2_765 ?
C32 C33 H33A 109.5 . . ?
C33 C33 H33A 109.5 2_765 . ?
C32 C33 H33B 109.5 . . ?
C33 C33 H33B 109.5 2_765 . ?
H33A C33 H33B 108.1 . . ?
C31 O31A H31 109.5 . . ?
H1W O1W H2W 111(3) . . ?
 
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
O31A H31 O1B  0.84 1.62 2.4609(14) 174.8 .
O1W H2W O1A  0.839(15) 2.008(16) 2.8357(16) 169(2) .
N21 H21 O31B  0.88 1.86 2.7277(15) 167.0 2_675
N23 H23 O1A  0.88 1.88 2.7529(15) 173.3 2_765
O1W H1W O1W  0.814(18) 2.16(4) 2.723(3) 126(4) 2_756
 
_diffrn_measured_fraction_theta_max    0.957
_diffrn_reflns_theta_full              25.83
_diffrn_measured_fraction_theta_full   0.957
_refine_diff_density_max    0.383
_refine_diff_density_min   -0.293
_refine_diff_density_rms    0.057
