 
data_07skc0010cc
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
adipic acid & hexamethyleneimine
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C12 H23 N O4'
_chemical_formula_weight          245.31
 
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    Cc
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 'x, -y, z+1/2'
 'x+1/2, y+1/2, z'
 'x+1/2, -y+1/2, z+1/2'
 
_cell_length_a                    13.8261(10)
_cell_length_b                    11.0607(10)
_cell_length_c                    9.6798(9)
_cell_angle_alpha                 90.00
_cell_angle_beta                  115.478(7)
_cell_angle_gamma                 90.00
_cell_volume                      1336.3(2)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     2755
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        fragment
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.12
_exptl_crystal_size_mid           0.06
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.219
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              536
_exptl_absorpt_coefficient_mu     0.090
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9892
_exptl_absorpt_correction_T_max   0.9982
_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             10127
_diffrn_reflns_av_R_equivalents   0.0670
_diffrn_reflns_av_sigmaI/netI     0.0398
_diffrn_reflns_limit_h_min        -17
_diffrn_reflns_limit_h_max        17
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -12
_diffrn_reflns_limit_l_max        12
_diffrn_reflns_theta_min          3.26
_diffrn_reflns_theta_max          27.48
_reflns_number_total              1536
_reflns_number_gt                 1348
_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)+(0.0302P)²+1.0785P] 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          1536
_refine_ls_number_parameters      158
_refine_ls_number_restraints      2
_refine_ls_R_factor_all           0.0541
_refine_ls_R_factor_gt            0.0438
_refine_ls_wR_factor_ref          0.0993
_refine_ls_wR_factor_gt           0.0932
_refine_ls_goodness_of_fit_ref    1.108
_refine_ls_restrained_S_all       1.107
_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 0.1345(2) 0.8542(3) 0.0512(3) 0.0243(6) Uani 1 1 d . . .
C2 C 0.2101(3) 0.8470(3) 0.2178(3) 0.0269(6) Uani 1 1 d . . .
H2A H 0.1766 0.8871 0.2778 0.032 Uiso 1 1 calc R . .
H2B H 0.2761 0.8923 0.2352 0.032 Uiso 1 1 calc R . .
C3 C 0.2409(2) 0.7183(3) 0.2776(3) 0.0233(6) Uani 1 1 d . . .
H3A H 0.2715 0.6761 0.2151 0.028 Uiso 1 1 calc R . .
H3B H 0.1760 0.6738 0.2669 0.028 Uiso 1 1 calc R . .
C4 C 0.3226(2) 0.7174(3) 0.4452(3) 0.0250(6) Uani 1 1 d . . .
H4A H 0.3864 0.7644 0.4558 0.030 Uiso 1 1 calc R . .
H4B H 0.2911 0.7577 0.5075 0.030 Uiso 1 1 calc R . .
C5 C 0.3574(2) 0.5909(3) 0.5065(3) 0.0235(6) Uani 1 1 d . . .
H5A H 0.2928 0.5425 0.4883 0.028 Uiso 1 1 calc R . .
H5B H 0.3931 0.5529 0.4481 0.028 Uiso 1 1 calc R . .
C6 C 0.4325(2) 0.5857(2) 0.6750(3) 0.0211(6) Uani 1 1 d . . .
O1A O 0.11315(18) 0.96739(17) 0.0026(2) 0.0334(6) Uani 1 1 d . . .
H1 H 0.0681 0.9679 -0.0895 0.050(12) Uiso 1 1 calc R . .
O1B O 0.09722(19) 0.76757(19) -0.0307(2) 0.0374(6) Uani 1 1 d . . .
O6A O 0.47976(18) 0.48500(19) 0.7245(2) 0.0317(5) Uani 1 1 d . . .
O6B O 0.44357(19) 0.67504(19) 0.7574(2) 0.0364(6) Uani 1 1 d . . .
C22 C -0.0722(3) 1.2876(3) 0.0824(4) 0.0300(7) Uani 1 1 d . . .
H22A H -0.0413 1.3209 0.1876 0.036 Uiso 1 1 calc R . .
H22B H -0.1375 1.2418 0.0673 0.036 Uiso 1 1 calc R . .
C23 C -0.1028(2) 1.3910(3) -0.0308(4) 0.0304(7) Uani 1 1 d . . .
H23A H -0.1683 1.4295 -0.0339 0.036 Uiso 1 1 calc R . .
H23B H -0.1210 1.3571 -0.1338 0.036 Uiso 1 1 calc R . .
C24 C -0.0180(3) 1.4888(3) 0.0013(4) 0.0339(7) Uani 1 1 d . . .
H24A H -0.0448 1.5475 -0.0842 0.041 Uiso 1 1 calc R . .
H24B H -0.0090 1.5326 0.0953 0.041 Uiso 1 1 calc R . .
C25 C 0.0914(3) 1.4438(3) 0.0217(4) 0.0326(7) Uani 1 1 d . . .
H25A H 0.1367 1.5143 0.0255 0.039 Uiso 1 1 calc R . .
H25B H 0.0824 1.3945 -0.0685 0.039 Uiso 1 1 calc R . .
C26 C 0.1493(2) 1.3681(3) 0.1661(4) 0.0305(7) Uani 1 1 d . . .
H26A H 0.2274 1.3784 0.2011 0.037 Uiso 1 1 calc R . .
H26B H 0.1310 1.4006 0.2472 0.037 Uiso 1 1 calc R . .
C27 C 0.1241(2) 1.2341(3) 0.1493(3) 0.0272(6) Uani 1 1 d . . .
H27A H 0.1622 1.1968 0.0937 0.033 Uiso 1 1 calc R . .
H27B H 0.1531 1.1976 0.2526 0.033 Uiso 1 1 calc R . .
N21 N 0.00720(19) 1.2026(2) 0.0670(3) 0.0249(5) Uani 1 1 d . . .
H21A H -0.0096 1.1954 -0.0355 0.026(8) Uiso 1 1 calc R . .
H21B H -0.0023 1.1277 0.1006 0.052(12) 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 1.208(3) . ?
C1 O1A 1.325(3) . ?
C1 C2 1.500(4) . ?
C2 C3 1.526(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.527(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.515(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.511(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O6B 1.238(3) . ?
C6 O6A 1.276(3) . ?
O1A H1 0.8400 . ?
C22 N21 1.500(4) . ?
C22 C23 1.513(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.526(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.523(5) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.527(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.515(4) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 N21 1.504(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
N21 H21A 0.9200 . ?
N21 H21B 0.9200 . ?
 
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 123.3(3) . . ?
O1B C1 C2 124.5(2) . . ?
O1A C1 C2 112.2(2) . . ?
C1 C2 C3 114.1(2) . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
C3 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C2 C3 C4 111.6(2) . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C5 C4 C3 112.8(2) . . ?
C5 C4 H4A 109.0 . . ?
C3 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C3 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C6 C5 C4 114.4(2) . . ?
C6 C5 H5A 108.7 . . ?
C4 C5 H5A 108.7 . . ?
C6 C5 H5B 108.7 . . ?
C4 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
O6B C6 O6A 123.6(3) . . ?
O6B C6 C5 120.1(2) . . ?
O6A C6 C5 116.3(2) . . ?
C1 O1A H1 109.5 . . ?
N21 C22 C23 112.9(3) . . ?
N21 C22 H22A 109.0 . . ?
C23 C22 H22A 109.0 . . ?
N21 C22 H22B 109.0 . . ?
C23 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
C22 C23 C24 115.9(3) . . ?
C22 C23 H23A 108.3 . . ?
C24 C23 H23A 108.3 . . ?
C22 C23 H23B 108.3 . . ?
C24 C23 H23B 108.3 . . ?
H23A C23 H23B 107.4 . . ?
C25 C24 C23 115.3(3) . . ?
C25 C24 H24A 108.4 . . ?
C23 C24 H24A 108.4 . . ?
C25 C24 H24B 108.4 . . ?
C23 C24 H24B 108.4 . . ?
H24A C24 H24B 107.5 . . ?
C24 C25 C26 113.4(3) . . ?
C24 C25 H25A 108.9 . . ?
C26 C25 H25A 108.9 . . ?
C24 C25 H25B 108.9 . . ?
C26 C25 H25B 108.9 . . ?
H25A C25 H25B 107.7 . . ?
C27 C26 C25 115.6(3) . . ?
C27 C26 H26A 108.4 . . ?
C25 C26 H26A 108.4 . . ?
C27 C26 H26B 108.4 . . ?
C25 C26 H26B 108.4 . . ?
H26A C26 H26B 107.4 . . ?
N21 C27 C26 115.4(2) . . ?
N21 C27 H27A 108.4 . . ?
C26 C27 H27A 108.4 . . ?
N21 C27 H27B 108.4 . . ?
C26 C27 H27B 108.4 . . ?
H27A C27 H27B 107.5 . . ?
C22 N21 C27 117.9(2) . . ?
C22 N21 H21A 107.8 . . ?
C27 N21 H21A 107.8 . . ?
C22 N21 H21B 107.8 . . ?
C27 N21 H21B 107.8 . . ?
H21A N21 H21B 107.2 . . ?
 
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
O1A H1 O6A  0.84 1.70 2.533(3) 173.9 3_454
N21 H21A O6B  0.92 1.84 2.753(3) 174.1 3_454
N21 H21B O6A  0.92 1.82 2.697(3) 158.6 4_464
 
_diffrn_measured_fraction_theta_max    0.999
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.999
_refine_diff_density_max    0.158
_refine_diff_density_min   -0.200
_refine_diff_density_rms    0.044
