 
data_07skc0004p21c
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
Maleic acid + morpholine
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C10 H17 N O5'
_chemical_formula_weight          231.25
 
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            monoclinic
_symmetry_space_group_name_H-M    P21/c
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    5.7683(9)
_cell_length_b                    13.702(3)
_cell_length_c                    14.442(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  97.458(11)
_cell_angle_gamma                 90.00
_cell_volume                      1131.8(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     3704
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        needle
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.18
_exptl_crystal_size_mid           0.02
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.357
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              496
_exptl_absorpt_coefficient_mu     0.109
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9808
_exptl_absorpt_correction_T_max   0.9989
_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             12271
_diffrn_reflns_av_R_equivalents   0.1974
_diffrn_reflns_av_sigmaI/netI     0.1928
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_k_min        -17
_diffrn_reflns_limit_k_max        17
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          2.97
_diffrn_reflns_theta_max          27.48
_reflns_number_total              2590
_reflns_number_gt                 1150
_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)+(0.0425P)²+9.2255P] 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          2590
_refine_ls_number_parameters      147
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.2800
_refine_ls_R_factor_gt            0.1456
_refine_ls_wR_factor_ref          0.3147
_refine_ls_wR_factor_gt           0.2528
_refine_ls_goodness_of_fit_ref    1.121
_refine_ls_restrained_S_all       1.121
_refine_ls_shift/su_max           0.003
_refine_ls_shift/su_mean          0.001
 
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 -0.2485(12) 1.0650(6) 0.0988(5) 0.0289(18) Uani 1 1 d . . .
C2 C -0.2177(13) 0.9551(6) 0.0987(5) 0.0292(18) Uani 1 1 d . . .
H2A H -0.3396 0.9242 0.1313 0.035 Uiso 1 1 calc R . .
H2B H -0.2370 0.9310 0.0335 0.035 Uiso 1 1 calc R . .
C3 C 0.0197(12) 0.9268(5) 0.1464(5) 0.0247(17) Uani 1 1 d . . .
H3 H 0.1393 0.9671 0.1196 0.030 Uiso 1 1 calc R . .
C4 C 0.0672(13) 0.8196(6) 0.1276(5) 0.0275(18) Uani 1 1 d . . .
C5 C -0.5232(13) 1.1905(6) 0.1047(6) 0.035(2) Uani 1 1 d . . .
H5A H -0.4086 1.2276 0.1468 0.052 Uiso 1 1 calc R . .
H5B H -0.6797 1.2008 0.1225 0.052 Uiso 1 1 calc R . .
H5C H -0.5203 1.2128 0.0404 0.052 Uiso 1 1 calc R . .
C6 C 0.3591(14) 0.6992(6) 0.1369(6) 0.035(2) Uani 1 1 d . . .
H6A H 0.2909 0.6600 0.1833 0.053 Uiso 1 1 calc R . .
H6B H 0.5296 0.6919 0.1464 0.053 Uiso 1 1 calc R . .
H6C H 0.2976 0.6769 0.0740 0.053 Uiso 1 1 calc R . .
C22 C 0.2706(13) 0.9753(6) 0.2902(5) 0.0295(19) Uani 1 1 d . . .
H22A H 0.3303 1.0303 0.2556 0.035 Uiso 1 1 calc R . .
H22B H 0.3770 0.9190 0.2875 0.035 Uiso 1 1 calc R . .
C23 C 0.2614(14) 1.0044(6) 0.3912(5) 0.0303(19) Uani 1 1 d . . .
H23A H 0.4206 1.0219 0.4206 0.036 Uiso 1 1 calc R . .
H23B H 0.1606 1.0626 0.3930 0.036 Uiso 1 1 calc R . .
C25 C -0.0579(13) 0.9036(6) 0.4021(5) 0.033(2) Uani 1 1 d . . .
H25A H -0.1617 0.9608 0.4046 0.039 Uiso 1 1 calc R . .
H25B H -0.1175 0.8504 0.4390 0.039 Uiso 1 1 calc R . .
C26 C -0.0622(13) 0.8710(6) 0.3018(5) 0.0317(19) Uani 1 1 d . . .
H26A H 0.0321 0.8109 0.2994 0.038 Uiso 1 1 calc R . .
H26B H -0.2248 0.8562 0.2745 0.038 Uiso 1 1 calc R . .
N21 N 0.0341(10) 0.9491(5) 0.2477(4) 0.0256(14) Uani 1 1 d . . .
O1A O -0.1029(9) 1.1236(4) 0.0857(4) 0.0413(16) Uani 1 1 d . . .
O1B O -0.4669(9) 1.0895(4) 0.1111(4) 0.0307(13) Uani 1 1 d . . .
O4A O 0.2992(9) 0.8007(4) 0.1472(4) 0.0329(14) Uani 1 1 d . . .
O4B O -0.0764(9) 0.7598(4) 0.1020(4) 0.0345(14) Uani 1 1 d . . .
O24 O 0.1742(9) 0.9288(4) 0.4420(4) 0.0353(14) Uani 1 1 d . . .
 
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 0.019(4) 0.041(5) 0.025(4) -0.001(4) -0.003(3) 0.005(4)
C2 0.034(4) 0.022(4) 0.029(4) 0.002(4) -0.006(3) 0.004(4)
C3 0.024(4) 0.021(4) 0.029(4) -0.002(3) 0.006(3) 0.001(3)
C4 0.025(4) 0.030(5) 0.028(4) 0.002(4) 0.004(3) -0.001(4)
C5 0.027(4) 0.035(5) 0.042(5) 0.004(4) 0.004(4) -0.003(4)
C6 0.039(5) 0.022(5) 0.042(5) -0.007(4) -0.002(4) 0.009(4)
C22 0.026(4) 0.031(5) 0.030(4) 0.007(4) -0.005(3) -0.004(3)
C23 0.037(5) 0.026(5) 0.026(4) 0.003(4) -0.001(4) 0.003(4)
C25 0.030(4) 0.038(5) 0.030(4) 0.005(4) 0.008(4) -0.006(4)
C26 0.021(4) 0.039(5) 0.035(4) -0.006(4) 0.005(4) -0.001(4)
N21 0.023(3) 0.026(4) 0.029(3) 0.000(3) 0.005(3) -0.003(3)
O1A 0.028(3) 0.035(4) 0.062(4) 0.003(3) 0.008(3) -0.005(3)
O1B 0.026(3) 0.030(3) 0.038(3) -0.001(3) 0.008(2) 0.006(2)
O4A 0.027(3) 0.029(3) 0.043(3) -0.008(3) 0.003(3) 0.007(2)
O4B 0.026(3) 0.036(4) 0.041(3) -0.002(3) 0.004(3) -0.002(3)
O24 0.041(3) 0.038(4) 0.026(3) 0.003(3) -0.002(2) -0.008(3)
 
_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 1.195(9) . ?
C1 O1B 1.337(8) . ?
C1 C2 1.516(11) . ?
C2 C3 1.502(10) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N21 1.487(9) . ?
C3 C4 1.525(11) . ?
C3 H3 1.0000 . ?
C4 O4B 1.190(9) . ?
C4 O4A 1.356(9) . ?
C5 O1B 1.422(9) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 O4A 1.445(9) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C22 N21 1.465(9) . ?
C22 C23 1.519(11) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 O24 1.400(9) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C25 O24 1.429(9) . ?
C25 C26 1.513(10) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 N21 1.476(10) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
 
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 123.1(8) . . ?
O1A C1 C2 125.6(7) . . ?
O1B C1 C2 111.2(7) . . ?
C3 C2 C1 110.8(6) . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
N21 C3 C2 109.3(6) . . ?
N21 C3 C4 112.6(6) . . ?
C2 C3 C4 110.0(6) . . ?
N21 C3 H3 108.3 . . ?
C2 C3 H3 108.3 . . ?
C4 C3 H3 108.3 . . ?
O4B C4 O4A 124.2(7) . . ?
O4B C4 C3 125.8(7) . . ?
O4A C4 C3 110.0(6) . . ?
O1B C5 H5A 109.5 . . ?
O1B C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O1B C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O4A C6 H6A 109.5 . . ?
O4A C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O4A C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N21 C22 C23 108.6(6) . . ?
N21 C22 H22A 110.0 . . ?
C23 C22 H22A 110.0 . . ?
N21 C22 H22B 110.0 . . ?
C23 C22 H22B 110.0 . . ?
H22A C22 H22B 108.3 . . ?
O24 C23 C22 111.7(7) . . ?
O24 C23 H23A 109.3 . . ?
C22 C23 H23A 109.3 . . ?
O24 C23 H23B 109.3 . . ?
C22 C23 H23B 109.3 . . ?
H23A C23 H23B 107.9 . . ?
O24 C25 C26 110.8(6) . . ?
O24 C25 H25A 109.5 . . ?
C26 C25 H25A 109.5 . . ?
O24 C25 H25B 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 108.1 . . ?
N21 C26 C25 109.4(6) . . ?
N21 C26 H26A 109.8 . . ?
C25 C26 H26A 109.8 . . ?
N21 C26 H26B 109.8 . . ?
C25 C26 H26B 109.8 . . ?
H26A C26 H26B 108.2 . . ?
C22 N21 C26 110.5(6) . . ?
C22 N21 C3 113.1(6) . . ?
C26 N21 C3 113.3(6) . . ?
C1 O1B C5 116.6(6) . . ?
C4 O4A C6 113.9(6) . . ?
C23 O24 C25 110.4(6) . . ?
 
_diffrn_measured_fraction_theta_max    0.991
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.991
_refine_diff_density_max    0.477
_refine_diff_density_min   -0.430
_refine_diff_density_rms    0.110
