 
data_07skc0014
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
fumaric acid & 1-methylpiperazine
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C22 H36 N4 O12'
_chemical_formula_weight          548.55
 
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                    6.7452(3)
_cell_length_b                    8.7155(5)
_cell_length_c                    11.3058(6)
_cell_angle_alpha                 101.834(3)
_cell_angle_beta                  91.509(3)
_cell_angle_gamma                 92.367(3)
_cell_volume                      649.55(6)
_cell_formula_units_Z             1
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     2815
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.16
_exptl_crystal_size_mid           0.07
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.402
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              292
_exptl_absorpt_coefficient_mu     0.115
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9819
_exptl_absorpt_correction_T_max   0.9977
_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             8705
_diffrn_reflns_av_R_equivalents   0.0569
_diffrn_reflns_av_sigmaI/netI     0.0723
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_theta_min          3.02
_diffrn_reflns_theta_max          27.48
_reflns_number_total              2952
_reflns_number_gt                 2106
_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)+(0.0000P)²+1.6339P] 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          2952
_refine_ls_number_parameters      176
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1131
_refine_ls_R_factor_gt            0.0761
_refine_ls_wR_factor_ref          0.1551
_refine_ls_wR_factor_gt           0.1351
_refine_ls_goodness_of_fit_ref    1.070
_refine_ls_restrained_S_all       1.070
_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 0.4063(4) 0.9642(3) 0.1273(3) 0.0175(6) Uani 1 1 d . . .
C2 C 0.5067(4) 0.8142(3) 0.1299(3) 0.0181(6) Uani 1 1 d . . .
H2 H 0.4632 0.7222 0.0730 0.022 Uiso 1 1 calc R . .
C3 C 0.6530(4) 0.8047(4) 0.2080(3) 0.0185(6) Uani 1 1 d . . .
H3 H 0.6994 0.8977 0.2629 0.022 Uiso 1 1 calc R . .
C4 C 0.7492(4) 0.6543(3) 0.2143(3) 0.0183(6) Uani 1 1 d . . .
O1A O 0.4730(3) 1.0883(2) 0.19832(19) 0.0194(5) Uani 1 1 d . . .
O1B O 0.2588(3) 0.9578(2) 0.05575(19) 0.0220(5) Uani 1 1 d . . .
O4A O 0.6926(3) 0.5314(2) 0.1401(2) 0.0223(5) Uani 1 1 d . . .
O4B O 0.8833(3) 0.6604(3) 0.2961(2) 0.0258(5) Uani 1 1 d . . .
C22 C 0.0713(4) 0.2983(4) 0.3223(3) 0.0180(6) Uani 1 1 d . . .
H22A H 0.0068 0.3976 0.3542 0.022 Uiso 1 1 calc R . .
H22B H 0.1003 0.2470 0.3909 0.022 Uiso 1 1 calc R . .
C23 C -0.0668(4) 0.1924(3) 0.2314(3) 0.0182(6) Uani 1 1 d . . .
H23A H -0.0069 0.0898 0.2046 0.022 Uiso 1 1 calc R . .
H23B H -0.1937 0.1740 0.2695 0.022 Uiso 1 1 calc R . .
N24 N -0.1056(4) 0.2648(3) 0.1248(2) 0.0181(5) Uani 1 1 d . . .
H24A H -0.1835 0.1958 0.0681 0.022 Uiso 1 1 calc R . .
H24B H -0.1746 0.3541 0.1487 0.022 Uiso 1 1 calc R . .
C25 C 0.0814(4) 0.3055(4) 0.0690(3) 0.0187(6) Uani 1 1 d . . .
H25A H 0.0501 0.3590 0.0021 0.022 Uiso 1 1 calc R . .
H25B H 0.1488 0.2082 0.0350 0.022 Uiso 1 1 calc R . .
C26 C 0.2182(4) 0.4113(3) 0.1615(3) 0.0184(6) Uani 1 1 d . . .
H26A H 0.3438 0.4343 0.1237 0.022 Uiso 1 1 calc R . .
H26B H 0.1551 0.5118 0.1915 0.022 Uiso 1 1 calc R . .
C27 C 0.4027(5) 0.4295(4) 0.3562(3) 0.0241(7) Uani 1 1 d . . .
H27A H 0.5256 0.4517 0.3172 0.036 Uiso 1 1 calc R . .
H27B H 0.4326 0.3720 0.4200 0.036 Uiso 1 1 calc R . .
H27C H 0.3432 0.5284 0.3917 0.036 Uiso 1 1 calc R . .
N21 N 0.2612(3) 0.3329(3) 0.2648(2) 0.0157(5) Uani 1 1 d . . .
H21 H 0.3182 0.2381 0.2344 0.040(11) Uiso 1 1 calc R . .
C31 C 0.7407(5) 1.1203(4) 0.5552(3) 0.0209(7) Uani 1 1 d . . .
C32 C 0.5745(5) 1.0009(4) 0.5392(3) 0.0223(7) Uani 1 1 d . . .
H32 H 0.5751 0.9229 0.5868 0.027 Uiso 1 1 calc R . .
O31A O 0.7498(3) 1.2263(3) 0.4999(2) 0.0258(5) Uani 1 1 d . . .
O31B O 0.8766(4) 1.0999(3) 0.6365(2) 0.0282(6) Uani 1 1 d . . .
H31B H 0.9577 1.1777 0.6510 0.060(15) 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 1.258(3) . ?
C1 O1A 1.265(4) . ?
C1 C2 1.502(4) . ?
C2 C3 1.324(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.500(4) . ?
C3 H3 0.9500 . ?
C4 O4A 1.256(4) . ?
C4 O4B 1.268(4) . ?
C22 N21 1.498(4) . ?
C22 C23 1.505(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 N24 1.493(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
N24 C25 1.487(4) . ?
N24 H24A 0.9200 . ?
N24 H24B 0.9200 . ?
C25 C26 1.510(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 N21 1.497(4) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 N21 1.488(4) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
N21 H21 0.9300 . ?
C31 O31A 1.218(4) . ?
C31 O31B 1.324(4) . ?
C31 C32 1.479(4) . ?
C32 C32 1.320(6) 2_676 ?
C32 H32 0.9500 . ?
O31B H31B 0.8400 . ?
 
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 124.1(3) . . ?
O1B C1 C2 117.7(3) . . ?
O1A C1 C2 118.2(2) . . ?
C3 C2 C1 122.9(3) . . ?
C3 C2 H2 118.6 . . ?
C1 C2 H2 118.6 . . ?
C2 C3 C4 123.3(3) . . ?
C2 C3 H3 118.4 . . ?
C4 C3 H3 118.4 . . ?
O4A C4 O4B 124.3(3) . . ?
O4A C4 C3 118.8(3) . . ?
O4B C4 C3 116.9(3) . . ?
N21 C22 C23 110.4(2) . . ?
N21 C22 H22A 109.6 . . ?
C23 C22 H22A 109.6 . . ?
N21 C22 H22B 109.6 . . ?
C23 C22 H22B 109.6 . . ?
H22A C22 H22B 108.1 . . ?
N24 C23 C22 110.4(2) . . ?
N24 C23 H23A 109.6 . . ?
C22 C23 H23A 109.6 . . ?
N24 C23 H23B 109.6 . . ?
C22 C23 H23B 109.6 . . ?
H23A C23 H23B 108.1 . . ?
C25 N24 C23 111.9(2) . . ?
C25 N24 H24A 109.2 . . ?
C23 N24 H24A 109.2 . . ?
C25 N24 H24B 109.2 . . ?
C23 N24 H24B 109.2 . . ?
H24A N24 H24B 107.9 . . ?
N24 C25 C26 110.7(2) . . ?
N24 C25 H25A 109.5 . . ?
C26 C25 H25A 109.5 . . ?
N24 C25 H25B 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 108.1 . . ?
N21 C26 C25 109.7(2) . . ?
N21 C26 H26A 109.7 . . ?
C25 C26 H26A 109.7 . . ?
N21 C26 H26B 109.7 . . ?
C25 C26 H26B 109.7 . . ?
H26A C26 H26B 108.2 . . ?
N21 C27 H27A 109.5 . . ?
N21 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N21 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C27 N21 C26 111.9(2) . . ?
C27 N21 C22 110.4(2) . . ?
C26 N21 C22 109.8(2) . . ?
C27 N21 H21 108.2 . . ?
C26 N21 H21 108.2 . . ?
C22 N21 H21 108.2 . . ?
O31A C31 O31B 124.0(3) . . ?
O31A C31 C32 123.3(3) . . ?
O31B C31 C32 112.7(3) . . ?
C32 C32 C31 122.2(4) 2_676 . ?
C32 C32 H32 118.9 2_676 . ?
C31 C32 H32 118.9 . . ?
C31 O31B H31B 109.5 . . ?
 
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
N21 H21 O1A  0.93 1.70 2.608(3) 165.7 1_545
O31B H31B O4B  0.84 1.73 2.563(3) 171.2 2_776
N24 H24A O1B  0.92 1.77 2.664(3) 161.9 2_565
N24 H24B O4A  0.92 1.84 2.719(3) 160.0 1_455
 
_diffrn_measured_fraction_theta_max    0.986
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.986
_refine_diff_density_max    0.315
_refine_diff_density_min   -0.310
_refine_diff_density_rms    0.078
