 
data_07skc0007p21c
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
Fumaric acid & 1,1,3,3-tetramethylbutylamine
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C20 H42 N2 O4'
_chemical_formula_weight          374.56
 
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                    11.569(10)
_cell_length_b                    6.307(5)
_cell_length_c                    16.676(13)
_cell_angle_alpha                 90.00
_cell_angle_beta                  101.54(5)
_cell_angle_gamma                 90.00
_cell_volume                      1192.1(17)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     1536
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.17
_exptl_crystal_size_mid           0.10
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.043
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              416
_exptl_absorpt_coefficient_mu     0.071
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9880
_exptl_absorpt_correction_T_max   0.9993
_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             8414
_diffrn_reflns_av_R_equivalents   0.2200
_diffrn_reflns_av_sigmaI/netI     0.3003
_diffrn_reflns_limit_h_min        -15
_diffrn_reflns_limit_h_max        15
_diffrn_reflns_limit_k_min        -7
_diffrn_reflns_limit_k_max        8
_diffrn_reflns_limit_l_min        -21
_diffrn_reflns_limit_l_max        21
_diffrn_reflns_theta_min          3.35
_diffrn_reflns_theta_max          27.48
_reflns_number_total              2606
_reflns_number_gt                 788
_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)+(0.0785P)²+5.9945P] 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          2606
_refine_ls_number_parameters      127
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.4101
_refine_ls_R_factor_gt            0.1926
_refine_ls_wR_factor_ref          0.4242
_refine_ls_wR_factor_gt           0.3174
_refine_ls_goodness_of_fit_ref    1.079
_refine_ls_restrained_S_all       1.079
_refine_ls_shift/su_max           0.002
_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 -0.0137(8) -0.322(2) 0.5912(6) 0.050(3) Uani 1 1 d . . .
C2 C 0.0037(8) -0.3974(15) 0.5110(6) 0.052(3) Uani 1 1 d . . .
H2 H 0.0210 -0.2962 0.4729 0.063 Uiso 1 1 calc R . .
O1A O -0.0045(7) -0.4432(12) 0.6505(4) 0.069(2) Uani 1 1 d . . .
O1B O -0.0414(6) -0.1264(13) 0.5943(4) 0.061(2) Uani 1 1 d . . .
C21 C 0.3366(9) 0.153(2) 0.5165(6) 0.073(4) Uani 1 1 d . . .
H21A H 0.2597 0.1154 0.4829 0.109 Uiso 1 1 calc R . .
H21B H 0.3995 0.0890 0.4929 0.109 Uiso 1 1 calc R . .
H21C H 0.3456 0.3073 0.5179 0.109 Uiso 1 1 calc R . .
C22 C 0.3442(10) 0.070(2) 0.6027(6) 0.066(3) Uani 1 1 d . . .
C23 C 0.2293(8) 0.1389(16) 0.6278(5) 0.052(3) Uani 1 1 d . . .
H23A H 0.1648 0.0592 0.5924 0.063 Uiso 1 1 calc R . .
H23B H 0.2173 0.2901 0.6124 0.063 Uiso 1 1 calc R . .
C24 C 0.2084(8) 0.1192(17) 0.7159(6) 0.053(3) Uani 1 1 d . . .
C26 C 0.4560(9) 0.1548(19) 0.6583(6) 0.071(3) Uani 1 1 d . . .
H26A H 0.5246 0.1204 0.6345 0.106 Uiso 1 1 calc R . .
H26B H 0.4650 0.0892 0.7125 0.106 Uiso 1 1 calc R . .
H26C H 0.4500 0.3090 0.6635 0.106 Uiso 1 1 calc R . .
C27 C 0.3523(10) -0.1726(18) 0.5974(7) 0.074(3) Uani 1 1 d . . .
H27A H 0.2759 -0.2297 0.5698 0.111 Uiso 1 1 calc R . .
H27B H 0.3733 -0.2320 0.6527 0.111 Uiso 1 1 calc R . .
H27C H 0.4128 -0.2108 0.5664 0.111 Uiso 1 1 calc R . .
C28 C 0.2288(9) -0.1025(18) 0.7544(6) 0.070(3) Uani 1 1 d . . .
H28A H 0.1991 -0.1060 0.8055 0.105 Uiso 1 1 calc R . .
H28B H 0.3134 -0.1345 0.7660 0.105 Uiso 1 1 calc R . .
H28C H 0.1868 -0.2082 0.7164 0.105 Uiso 1 1 calc R . .
C29 C 0.2690(11) 0.2916(19) 0.7740(6) 0.079(4) Uani 1 1 d . . .
H29A H 0.2478 0.4314 0.7497 0.118 Uiso 1 1 calc R . .
H29B H 0.3547 0.2729 0.7830 0.118 Uiso 1 1 calc R . .
H29C H 0.2432 0.2810 0.8263 0.118 Uiso 1 1 calc R . .
N25 N 0.0777(7) 0.1571(14) 0.7062(5) 0.054(2) Uani 1 1 d . . .
H25A H 0.0601 0.2907 0.6870 0.08(4) Uiso 1 1 calc R . .
H25B H 0.0564 0.1419 0.7555 0.04(2) Uiso 1 1 calc R . .
H25C H 0.0376 0.0614 0.6701 0.06(3) Uiso 1 1 calc R . .
 
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 0.032(6) 0.075(9) 0.048(6) 0.009(7) 0.018(5) 0.004(6)
C2 0.041(6) 0.075(8) 0.043(5) 0.009(6) 0.014(4) 0.000(6)
O1A 0.089(6) 0.068(5) 0.056(4) 0.008(4) 0.032(4) 0.002(4)
O1B 0.060(5) 0.069(5) 0.053(4) -0.005(4) 0.009(3) 0.004(4)
C21 0.054(7) 0.115(10) 0.055(6) 0.005(7) 0.024(5) -0.001(7)
C22 0.062(8) 0.087(9) 0.055(6) -0.001(7) 0.028(6) -0.009(7)
C23 0.053(7) 0.059(7) 0.049(6) -0.004(5) 0.020(5) -0.005(6)
C24 0.035(6) 0.069(8) 0.054(6) -0.002(6) 0.003(5) 0.003(5)
C26 0.054(7) 0.093(9) 0.065(7) 0.003(7) 0.012(6) -0.003(7)
C27 0.068(8) 0.087(10) 0.069(7) -0.015(7) 0.021(6) 0.008(7)
C28 0.055(7) 0.085(9) 0.068(7) 0.018(7) 0.010(6) 0.005(7)
C29 0.085(9) 0.100(9) 0.055(7) -0.019(7) 0.024(6) -0.022(8)
N25 0.070(6) 0.053(7) 0.042(5) -0.003(5) 0.022(4) -0.007(5)
 
_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 1.238(11) . ?
C1 O1B 1.276(12) . ?
C1 C2 1.472(13) . ?
C2 C2 1.343(19) 3_546 ?
C2 H2 0.9500 . ?
C21 C22 1.514(13) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C26 1.528(14) . ?
C22 C23 1.533(13) . ?
C22 C27 1.539(15) . ?
C23 C24 1.541(12) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 N25 1.508(12) . ?
C24 C29 1.530(13) . ?
C24 C28 1.537(14) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
N25 H25A 0.9100 . ?
N25 H25B 0.9100 . ?
N25 H25C 0.9100 . ?
 
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 123.2(9) . . ?
O1A C1 C2 121.3(11) . . ?
O1B C1 C2 115.5(9) . . ?
C2 C2 C1 123.3(12) 3_546 . ?
C2 C2 H2 118.4 3_546 . ?
C1 C2 H2 118.4 . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C21 C22 C26 109.7(9) . . ?
C21 C22 C23 105.9(9) . . ?
C26 C22 C23 114.3(9) . . ?
C21 C22 C27 106.3(9) . . ?
C26 C22 C27 109.1(10) . . ?
C23 C22 C27 111.2(9) . . ?
C22 C23 C24 123.1(8) . . ?
C22 C23 H23A 106.5 . . ?
C24 C23 H23A 106.5 . . ?
C22 C23 H23B 106.5 . . ?
C24 C23 H23B 106.5 . . ?
H23A C23 H23B 106.5 . . ?
N25 C24 C29 106.1(8) . . ?
N25 C24 C28 104.8(8) . . ?
C29 C24 C28 111.7(8) . . ?
N25 C24 C23 103.3(7) . . ?
C29 C24 C23 114.0(9) . . ?
C28 C24 C23 115.6(9) . . ?
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 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C24 C28 H28A 109.5 . . ?
C24 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C24 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C24 C29 H29A 109.5 . . ?
C24 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C24 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C24 N25 H25A 109.5 . . ?
C24 N25 H25B 109.5 . . ?
H25A N25 H25B 109.5 . . ?
C24 N25 H25C 109.5 . . ?
H25A N25 H25C 109.5 . . ?
H25B N25 H25C 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
N25 H25C O1B  0.91 1.84 2.747(11) 177.9 .
N25 H25A O1A  0.91 1.89 2.787(12) 169.4 1_565
N25 H25B O1A  0.91 1.87 2.764(10) 168.7 2_556
 
_diffrn_measured_fraction_theta_max    0.956
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.956
_refine_diff_density_max    0.348
_refine_diff_density_min   -0.255
_refine_diff_density_rms    0.072
