#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/03/7200356.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7200356
loop_
_publ_author_name
'Portell, Anna'
'Barbas, Rafael'
'Font-Bardia, Mercè'
'Dalmases, Pere'
'Prohens, Rafel'
'Puigjaner, Cristina'
_publ_section_title
;
 Ziprasidone malate, a new trimorphic salt with improved aqueous
 solubility
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              791
_journal_paper_doi               10.1039/b813401d
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C21 H20 Cl N4 O S'
_chemical_formula_sum            'C21 H20 Cl N4 O S'
_chemical_formula_weight         411.92
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.60(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.377(8)
_cell_length_b                   8.038(3)
_cell_length_c                   33.627(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21
_cell_measurement_theta_min      12
_cell_volume                     1984(2)
_computing_cell_refinement       'CAD-4/PC (Kretschmar, 1996)'
_computing_data_collection       'CAD-4/PC (Kretschmar, 1996)'
_computing_data_reduction        'XCAD4 (Harms and Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP (Brueggermann and Smith, 1990)'
_computing_publication_material  'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Enraf-Nonius, CAD4'
_diffrn_measurement_method       ω--2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_sigmaI/netI    0.0755
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5790
_diffrn_reflns_theta_full        30.14
_diffrn_reflns_theta_max         30.14
_diffrn_reflns_theta_min         2.43
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             860
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.146
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         5790
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.1451
_refine_ls_R_factor_gt           0.0508
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1385P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1441
_refine_ls_wR_factor_ref         0.2362
_reflns_number_gt                3018
_reflns_number_total             5790
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b813401d.txt
_cod_data_source_block           annmc5a
_cod_original_sg_symbol_H-M      P21/a
_cod_database_code               7200356
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'
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 . . .
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'
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) . . ?
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_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 54841
