 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
Di-1-phenylethylammonium tartrate
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C20 H28 N2 O6'
_chemical_formula_weight          392.44
 
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    P21
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z'
 
_cell_length_a                    5.5528(6)
_cell_length_b                    16.0180(18)
_cell_length_c                    11.7768(19)
_cell_angle_alpha                 90.00
_cell_angle_beta                  103.378(9)
_cell_angle_gamma                 90.00
_cell_volume                      1019.1(2)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     2766
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.50
_exptl_crystal_size_mid           0.15
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.279
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              420
_exptl_absorpt_coefficient_mu     0.095
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9543
_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             7917
_diffrn_reflns_av_R_equivalents   0.0499
_diffrn_reflns_av_sigmaI/netI     0.0492
_diffrn_reflns_limit_h_min        -5
_diffrn_reflns_limit_h_max        6
_diffrn_reflns_limit_k_min        -19
_diffrn_reflns_limit_k_max        19
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_limit_l_max        15
_diffrn_reflns_theta_min          3.99
_diffrn_reflns_theta_max          27.48
_reflns_number_total              2248
_reflns_number_gt                 1972
_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)+(0.0391P)²+0.2379P] 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      SHELXL
_refine_ls_extinction_coef        0.042(5)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_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          2248
_refine_ls_number_parameters      256
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0520
_refine_ls_R_factor_gt            0.0398
_refine_ls_wR_factor_ref          0.0922
_refine_ls_wR_factor_gt           0.0860
_refine_ls_goodness_of_fit_ref    1.048
_refine_ls_restrained_S_all       1.047
_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 0.4356(5) 0.18242(17) 0.0086(2) 0.0224(6) Uani 1 1 d . . .
C2 C 0.2905(5) 0.10323(16) 0.0205(2) 0.0205(5) Uani 1 1 d . . .
H2 H 0.3708 0.0563 -0.0130 0.025 Uiso 1 1 calc R . .
C3 C 0.3130(5) 0.08339(16) 0.1495(2) 0.0213(6) Uani 1 1 d . . .
H3 H 0.4922 0.0808 0.1901 0.026 Uiso 1 1 calc R . .
C4 C 0.1924(5) -0.00046(17) 0.1626(2) 0.0234(6) Uani 1 1 d . . .
O1A O 0.3231(4) 0.24359(12) -0.04610(18) 0.0311(5) Uani 1 1 d . . .
O1B O 0.6628(4) 0.18083(12) 0.05589(18) 0.0303(5) Uani 1 1 d . . .
O2 O 0.0407(4) 0.10575(12) -0.04080(17) 0.0258(4) Uani 1 1 d . . .
H2O H -0.0439 0.1296 0.0003 0.039 Uiso 1 1 calc R . .
O3 O 0.1964(4) 0.14834(12) 0.20033(17) 0.0265(5) Uani 1 1 d . . .
H3O H 0.0751 0.1287 0.2228 0.040 Uiso 1 1 calc R . .
O4A O 0.0104(4) -0.00007(13) 0.2082(2) 0.0350(5) Uani 1 1 d . . .
O4B O 0.2827(4) -0.06461(11) 0.12530(17) 0.0273(5) Uani 1 1 d . . .
C11 C 0.0352(5) -0.11062(16) 0.7733(2) 0.0213(6) Uani 1 1 d . . .
C12 C 0.0593(5) -0.02582(17) 0.7547(2) 0.0237(6) Uani 1 1 d . . .
H12 H -0.0182 0.0134 0.7953 0.028 Uiso 1 1 calc R . .
C13 C 0.1964(5) 0.00240(19) 0.6768(3) 0.0267(6) Uani 1 1 d . . .
H13 H 0.2122 0.0606 0.6648 0.032 Uiso 1 1 calc R . .
C14 C 0.3091(5) -0.05400(19) 0.6173(2) 0.0295(7) Uani 1 1 d . . .
H14 H 0.4013 -0.0347 0.5639 0.035 Uiso 1 1 calc R . .
C15 C 0.2878(5) -0.13873(19) 0.6356(3) 0.0313(7) Uani 1 1 d . . .
H15 H 0.3657 -0.1776 0.5948 0.038 Uiso 1 1 calc R . .
C16 C 0.1524(5) -0.16703(17) 0.7136(2) 0.0258(6) Uani 1 1 d . . .
H16 H 0.1397 -0.2253 0.7264 0.031 Uiso 1 1 calc R . .
C17 C -0.1180(5) -0.14396(16) 0.8545(2) 0.0216(5) Uani 1 1 d . . .
H17 H -0.2298 -0.1884 0.8118 0.026 Uiso 1 1 calc R . .
C18 C -0.2777(5) -0.07993(17) 0.8984(2) 0.0235(6) Uani 1 1 d . . .
H18A H -0.3892 -0.0531 0.8317 0.028 Uiso 1 1 calc R . .
H18B H -0.1713 -0.0376 0.9451 0.028 Uiso 1 1 calc R . .
H18C H -0.3754 -0.1079 0.9466 0.028 Uiso 1 1 calc R . .
N19 N 0.0482(4) -0.18342(13) 0.95997(18) 0.0219(5) Uani 1 1 d . . .
H19A H 0.1466 -0.2221 0.9366 0.026 Uiso 1 1 calc R . .
H19B H -0.0457 -0.2086 1.0040 0.026 Uiso 1 1 calc R . .
H19C H 0.1443 -0.1434 1.0031 0.026 Uiso 1 1 calc R . .
C21 C 0.3842(5) 0.26950(16) 0.6317(2) 0.0219(6) Uani 1 1 d . . .
C22 C 0.3136(6) 0.22694(18) 0.5262(3) 0.0286(6) Uani 1 1 d . . .
H22 H 0.1642 0.2419 0.4726 0.034 Uiso 1 1 calc R . .
C23 C 0.4582(6) 0.16286(18) 0.4982(3) 0.0308(7) Uani 1 1 d . . .
H23 H 0.4083 0.1344 0.4257 0.037 Uiso 1 1 calc R . .
C24 C 0.6750(6) 0.14073(19) 0.5763(3) 0.0297(7) Uani 1 1 d . . .
H24 H 0.7751 0.0972 0.5572 0.036 Uiso 1 1 calc R . .
C25 C 0.7462(5) 0.18122(18) 0.6812(3) 0.0296(6) Uani 1 1 d . . .
H25 H 0.8945 0.1653 0.7350 0.036 Uiso 1 1 calc R . .
C26 C 0.6013(5) 0.24583(18) 0.7093(3) 0.0267(6) Uani 1 1 d . . .
H26 H 0.6519 0.2738 0.7821 0.032 Uiso 1 1 calc R . .
C27 C 0.2266(5) 0.34218(16) 0.6530(2) 0.0218(6) Uani 1 1 d . . .
H27 H 0.0486 0.3266 0.6237 0.026 Uiso 1 1 calc R . .
C28 C 0.2770(6) 0.42077(17) 0.5891(3) 0.0280(6) Uani 1 1 d . . .
H28A H 0.2502 0.4089 0.5055 0.034 Uiso 1 1 calc R . .
H28B H 0.4486 0.4386 0.6196 0.034 Uiso 1 1 calc R . .
H28C H 0.1645 0.4653 0.6012 0.034 Uiso 1 1 calc R . .
N29 N 0.2686(4) 0.36312(13) 0.77922(19) 0.0224(5) Uani 1 1 d . . .
H29A H 0.2405 0.3171 0.8196 0.027 Uiso 1 1 calc R . .
H29B H 0.1634 0.4047 0.7889 0.027 Uiso 1 1 calc R . .
H29C H 0.4277 0.3804 0.8063 0.027 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 1.256(3) . ?
C1 O1A 1.257(3) . ?
C1 C2 1.526(4) . ?
C2 O2 1.409(3) . ?
C2 C3 1.529(4) . ?
C2 H2 1.0000 . ?
C3 O3 1.428(3) . ?
C3 C4 1.524(4) . ?
C3 H3 1.0000 . ?
C4 O4A 1.250(3) . ?
C4 O4B 1.266(3) . ?
O2 H2O 0.8400 . ?
O3 H3O 0.8400 . ?
C11 C12 1.387(4) . ?
C11 C16 1.394(4) . ?
C11 C17 1.517(4) . ?
C12 C13 1.396(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.391(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 N19 1.504(3) . ?
C17 C18 1.522(4) . ?
C17 H17 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
N19 H19A 0.9100 . ?
N19 H19B 0.9100 . ?
N19 H19C 0.9100 . ?
C21 C26 1.386(4) . ?
C21 C22 1.391(4) . ?
C21 C27 1.512(4) . ?
C22 C23 1.389(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.381(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.370(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.397(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 N29 1.489(4) . ?
C27 C28 1.525(4) . ?
C27 H27 1.0000 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
N29 H29A 0.9100 . ?
N29 H29B 0.9100 . ?
N29 H29C 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
O1B C1 O1A 124.9(3) . . ?
O1B C1 C2 116.1(2) . . ?
O1A C1 C2 119.0(2) . . ?
O2 C2 C1 114.0(2) . . ?
O2 C2 C3 111.1(2) . . ?
C1 C2 C3 109.9(2) . . ?
O2 C2 H2 107.2 . . ?
C1 C2 H2 107.2 . . ?
C3 C2 H2 107.2 . . ?
O3 C3 C4 110.3(2) . . ?
O3 C3 C2 108.9(2) . . ?
C4 C3 C2 110.3(2) . . ?
O3 C3 H3 109.1 . . ?
C4 C3 H3 109.1 . . ?
C2 C3 H3 109.1 . . ?
O4A C4 O4B 125.3(3) . . ?
O4A C4 C3 117.2(2) . . ?
O4B C4 C3 117.5(2) . . ?
C2 O2 H2O 109.5 . . ?
C3 O3 H3O 109.5 . . ?
C12 C11 C16 118.8(2) . . ?
C12 C11 C17 122.2(2) . . ?
C16 C11 C17 119.0(2) . . ?
C11 C12 C13 120.5(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 120.1(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 119.9(3) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 120.1(3) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 120.5(3) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
N19 C17 C11 110.0(2) . . ?
N19 C17 C18 107.3(2) . . ?
C11 C17 C18 115.6(2) . . ?
N19 C17 H17 107.9 . . ?
C11 C17 H17 107.9 . . ?
C18 C17 H17 107.9 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 N19 H19A 109.5 . . ?
C17 N19 H19B 109.5 . . ?
H19A N19 H19B 109.5 . . ?
C17 N19 H19C 109.5 . . ?
H19A N19 H19C 109.5 . . ?
H19B N19 H19C 109.5 . . ?
C26 C21 C22 118.5(3) . . ?
C26 C21 C27 123.3(2) . . ?
C22 C21 C27 118.1(3) . . ?
C23 C22 C21 121.0(3) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C24 C23 C22 119.6(3) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C25 C24 C23 120.3(3) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 120.1(3) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C21 C26 C25 120.5(3) . . ?
C21 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
N29 C27 C21 112.1(2) . . ?
N29 C27 C28 107.6(2) . . ?
C21 C27 C28 112.0(2) . . ?
N29 C27 H27 108.4 . . ?
C21 C27 H27 108.4 . . ?
C28 C27 H27 108.4 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 N29 H29A 109.5 . . ?
C27 N29 H29B 109.5 . . ?
H29A N29 H29B 109.5 . . ?
C27 N29 H29C 109.5 . . ?
H29A N29 H29C 109.5 . . ?
H29B N29 H29C 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
O2 H2O O3  0.84 2.44 2.853(3) 111.0 .
O3 H3O O4A  0.84 2.09 2.602(3) 118.6 .
O2 H2O O1B  0.84 2.06 2.872(3) 162.2 1_455
N19 H19A O1B  0.91 1.87 2.734(3) 157.6 2_646
N19 H19B O1A  0.91 1.89 2.760(3) 160.0 2_546
N19 H19C O4B  0.91 1.93 2.817(3) 162.8 1_556
N29 H29A O1A  0.91 1.94 2.775(3) 151.8 1_556
N29 H29B O4A  0.91 1.81 2.708(3) 168.4 2_556
N29 H29C O4B  0.91 1.85 2.741(3) 167.0 2_656
 
_diffrn_measured_fraction_theta_max    0.927
_diffrn_reflns_theta_full              25.00
_diffrn_measured_fraction_theta_full   0.995
_refine_diff_density_max    0.213
_refine_diff_density_min   -0.280
_refine_diff_density_rms    0.049
