# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Cristina Puigjaner'
_publ_contact_author_email       CRIS@SCT.UB.ES

_publ_section_title              
;
Ziprasidone malate, a new trimorphic salt with
improved aqueous solubility
;
loop_
_publ_author_name
'Cristina Puigjaner'
'Rafael Barbas'
'Pere Dalmases'
'Merce Font-Bardia'
'Anna Portell'
;
R.Prohens
;

# Attachment 'ZP.cif'

data_annmc5a
_database_code_depnum_ccdc_archive 'CCDC 694162'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H20 Cl N4 O S'
_chemical_formula_sum            'C21 H20 Cl N4 O S'
_chemical_formula_weight         411.92

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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/a

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'

_cell_length_a                   7.377(8)
_cell_length_b                   8.038(3)
_cell_length_c                   33.627(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.60(4)
_cell_angle_gamma                90.00
_cell_volume                     1984(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      12
_cell_measurement_theta_max      21

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             860
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf-Nonius, CAD4'
_diffrn_measurement_method       ω--2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  120
_diffrn_standards_decay_%        1
_diffrn_reflns_number            5790
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_sigmaI/netI    0.0755
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         30.14
_reflns_number_total             5790
_reflns_number_gt                3018
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CAD-4/PC (Kretschmar, 1996)'
_computing_cell_refinement       'CAD-4/PC (Kretschmar, 1996)'
_computing_data_reduction        'XCAD4 (Harms and Wocadlo, 1995)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP (Brueggermann and Smith, 1990)'
_computing_publication_material  'PLATON (Spek, 1990)'

_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)+(0.1385P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5790
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1451
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.2362
_refine_ls_wR_factor_gt          0.1441
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.995
_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
Cl Cl -0.03618(14) -0.10412(12) 0.33003(3) 0.0523(3) Uani 1 1 d . . .
S S 0.10620(12) 0.45754(11) 0.05251(3) 0.0421(3) Uani 1 1 d . . .
O O -0.2341(4) 0.3887(4) 0.50662(9) 0.0653(8) Uani 1 1 d . . .
N1 N -0.1856(4) 0.1910(5) 0.45999(10) 0.0453(8) Uani 1 1 d . . .
H1N H -0.202(6) 0.120(6) 0.4752(15) 0.069(16) Uiso 1 1 d . . .
N2 N 0.0397(3) 0.4312(3) 0.24282(8) 0.0325(6) Uani 1 1 d . . .
N4 N 0.0680(4) 0.4084(3) 0.09903(8) 0.0371(6) Uani 1 1 d . . .
N3 N 0.0172(3) 0.5327(3) 0.16065(7) 0.0304(6) Uani 1 1 d . . .
C1 C -0.0749(4) 0.0731(4) 0.35848(10) 0.0354(7) Uani 1 1 d . . .
C2 C -0.1189(5) 0.0453(4) 0.39717(11) 0.0398(7) Uani 1 1 d . . .
H2 H -0.1315 -0.0618 0.4070 0.048 Uiso 1 1 calc R . .
C3 C -0.1430(4) 0.1830(4) 0.42027(9) 0.0346(7) Uani 1 1 d . . .
C4 C -0.1987(5) 0.3493(5) 0.47293(11) 0.0449(8) Uani 1 1 d . . .
C5 C -0.1565(5) 0.4632(5) 0.43866(11) 0.0444(8) Uani 1 1 d . . .
H5 H -0.1507 0.5787 0.4384 0.053 Uiso 1 1 calc R . .
C6 C -0.1264(4) 0.3431(4) 0.40539(10) 0.0360(7) Uani 1 1 d . . .
C7 C -0.0891(4) 0.3671(4) 0.36675(10) 0.0365(7) Uani 1 1 d . . .
H7 H -0.0805 0.4745 0.3568 0.044 Uiso 1 1 calc R . .
C8 C -0.0637(4) 0.2295(4) 0.34190(9) 0.0312(6) Uani 1 1 d . . .
C9 C -0.0248(4) 0.2503(4) 0.29844(10) 0.0360(7) Uani 1 1 d . . .
H9A H 0.0887 0.1940 0.2949 0.043 Uiso 1 1 calc R . .
H9B H -0.1204 0.1942 0.2817 0.043 Uiso 1 1 calc R . .
C10 C -0.0114(4) 0.4274(4) 0.28364(10) 0.0354(7) Uani 1 1 d . . .
H10A H -0.1278 0.4826 0.2846 0.042 Uiso 1 1 calc R . .
H10B H 0.0787 0.4874 0.3010 0.042 Uiso 1 1 calc R . .
C11 C -0.1109(4) 0.3803(4) 0.21358(10) 0.0388(7) Uani 1 1 d . . .
H11A H -0.2096 0.4600 0.2136 0.047 Uiso 1 1 calc R . .
H11B H -0.1564 0.2726 0.2211 0.047 Uiso 1 1 calc R . .
C12 C -0.0491(4) 0.3700(4) 0.17251(10) 0.0362(7) Uani 1 1 d . . .
H12A H 0.0475 0.2882 0.1722 0.043 Uiso 1 1 calc R . .
H12B H -0.1497 0.3348 0.1537 0.043 Uiso 1 1 calc R . .
C13 C 0.1644(4) 0.5915(4) 0.18983(10) 0.0358(7) Uani 1 1 d . . .
H13A H 0.2026 0.7017 0.1824 0.043 Uiso 1 1 calc R . .
H13B H 0.2682 0.5175 0.1899 0.043 Uiso 1 1 calc R . .
C14 C 0.0999(5) 0.5970(4) 0.23095(11) 0.0407(8) Uani 1 1 d . . .
H14A H 0.1981 0.6353 0.2500 0.049 Uiso 1 1 calc R . .
H14B H -0.0003 0.6751 0.2311 0.049 Uiso 1 1 calc R . .
C15 C 0.0569(4) 0.5430(4) 0.12091(9) 0.0287(6) Uani 1 1 d . . .
C16 C 0.0788(4) 0.6991(4) 0.10045(9) 0.0287(6) Uani 1 1 d . . .
C17 C 0.0648(4) 0.8642(4) 0.11388(10) 0.0355(7) Uani 1 1 d . . .
H17 H 0.0416 0.8872 0.1400 0.043 Uiso 1 1 calc R . .
C18 C 0.0867(5) 0.9916(4) 0.08688(11) 0.0429(8) Uani 1 1 d . . .
H18 H 0.0760 1.1015 0.0950 0.051 Uiso 1 1 calc R . .
C19 C 0.1243(5) 0.9584(5) 0.04810(12) 0.0480(9) Uani 1 1 d . . .
H19 H 0.1432 1.0470 0.0312 0.058 Uiso 1 1 calc R . .
C20 C 0.1343(5) 0.8004(4) 0.03395(11) 0.0406(8) Uani 1 1 d . . .
H20 H 0.1548 0.7788 0.0076 0.049 Uiso 1 1 calc R . .
C21 C 0.1117(4) 0.6691(4) 0.06187(10) 0.0330(7) Uani 1 1 d . . .


_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
Cl C1 1.755(3) . ?
S N4 1.664(3) . ?
S C21 1.729(3) . ?
O C4 1.229(4) . ?
N1 C4 1.351(5) . ?
N1 C3 1.403(4) . ?
N1 H1N 0.78(5) . ?
N2 C10 1.459(4) . ?
N2 C11 1.468(4) . ?
N2 C14 1.472(4) . ?
N4 C15 1.316(4) . ?
N3 C15 1.398(4) . ?
N3 C12 1.465(4) . ?
N3 C13 1.469(4) . ?
C1 C8 1.381(4) . ?
C1 C2 1.390(5) . ?
C2 C3 1.374(5) . ?
C2 H2 0.9300 . ?
C3 C6 1.390(5) . ?
C4 C5 1.527(5) . ?
C5 C6 1.510(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.368(5) . ?
C7 C8 1.409(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.525(4) . ?
C9 C10 1.514(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.498(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.506(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.448(4) . ?
C16 C21 1.365(4) . ?
C16 C17 1.409(4) . ?
C17 C18 1.389(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.385(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.361(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.433(5) . ?
C20 H20 0.9300 . ?

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
N4 S C21 93.75(15) . . ?
C4 N1 C3 112.3(3) . . ?
C4 N1 H1N 117(4) . . ?
C3 N1 H1N 131(4) . . ?
C10 N2 C11 112.1(2) . . ?
C10 N2 C14 112.8(3) . . ?
C11 N2 C14 107.4(3) . . ?
C15 N4 S 110.9(2) . . ?
C15 N3 C12 114.8(2) . . ?
C15 N3 C13 114.2(2) . . ?
C12 N3 C13 110.5(2) . . ?
C8 C1 C2 123.6(3) . . ?
C8 C1 Cl 120.0(3) . . ?
C2 C1 Cl 116.4(3) . . ?
C3 C2 C1 117.0(3) . . ?
C3 C2 H2 121.5 . . ?
C1 C2 H2 121.5 . . ?
C2 C3 C6 121.4(3) . . ?
C2 C3 N1 128.9(3) . . ?
C6 C3 N1 109.6(3) . . ?
O C4 N1 124.6(4) . . ?
O C4 C5 128.2(4) . . ?
N1 C4 C5 107.2(3) . . ?
C6 C5 C4 103.4(3) . . ?
C6 C5 H5 128.3 . . ?
C4 C5 H5 128.3 . . ?
C7 C6 C3 120.3(3) . . ?
C7 C6 C5 132.2(3) . . ?
C3 C6 C5 107.5(3) . . ?
C6 C7 C8 120.2(3) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C1 C8 C7 117.3(3) . . ?
C1 C8 C9 120.7(3) . . ?
C7 C8 C9 122.0(3) . . ?
C10 C9 C8 116.2(3) . . ?
C10 C9 H9A 108.2 . . ?
C8 C9 H9A 108.2 . . ?
C10 C9 H9B 108.2 . . ?
C8 C9 H9B 108.2 . . ?
H9A C9 H9B 107.4 . . ?
N2 C10 C9 111.1(3) . . ?
N2 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
N2 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
N2 C11 C12 110.8(3) . . ?
N2 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
N3 C12 C11 110.0(3) . . ?
N3 C12 H12A 109.7 . . ?
C11 C12 H12A 109.7 . . ?
N3 C12 H12B 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
N3 C13 C14 110.1(3) . . ?
N3 C13 H13A 109.6 . . ?
C14 C13 H13A 109.6 . . ?
N3 C13 H13B 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.2 . . ?
N2 C14 C13 110.7(3) . . ?
N2 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
N4 C15 N3 121.1(3) . . ?
N4 C15 C16 115.5(3) . . ?
N3 C15 C16 123.3(3) . . ?
C21 C16 C17 119.8(3) . . ?
C21 C16 C15 109.7(3) . . ?
C17 C16 C15 130.5(3) . . ?
C18 C17 C16 117.9(3) . . ?
C18 C17 H17 121.0 . . ?
C16 C17 H17 121.0 . . ?
C19 C18 C17 121.4(3) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C20 C19 C18 122.1(3) . . ?
C20 C19 H19 118.9 . . ?
C18 C19 H19 118.9 . . ?
C19 C20 C21 116.4(3) . . ?
C19 C20 H20 121.8 . . ?
C21 C20 H20 121.8 . . ?
C16 C21 C20 122.4(3) . . ?
C16 C21 S 110.1(2) . . ?
C20 C21 S 127.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        30.14
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.146


