#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:12:22 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180416 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/85/7208579.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_7208579
loop_
_publ_author_name
'Bruni, Giovanna'
'Maietta, Mariarosa'
'Maggi, Lauretta'
'Bini, Marcella'
'Capsoni, Doretta'
'Ferrari, Stefania'
'Boiocchi, Massimo'
'Berbenni, Vittorio'
'Milanese, Chiara'
'Marini, Amedeo'
_publ_section_title
;
 Perphenazine--fumaric acid salts with improved solubility: preparation,
 physico-chemical characterization and in vitro dissolution
;
_journal_issue                   18
_journal_name_full               CrystEngComm
_journal_page_first              6035
_journal_paper_doi               10.1039/c2ce25846c
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C21 H27 Cl N3 O S, 0.5(C4 H2 O4)'
_chemical_formula_sum            'C23 H28 Cl N3 O3 S'
_chemical_formula_weight         462.00
_chemical_name_common            'Perphenazine fumarate'
_chemical_name_systematic
;

?

;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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                 115.94(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.964(7)
_cell_length_b                   30.082(5)
_cell_length_c                   9.428(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      7
_cell_volume                     2286(3)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       'omega scans'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4239
_diffrn_reflns_theta_full        25.51
_diffrn_reflns_theta_max         25.51
_diffrn_reflns_theta_min         1.35
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  300
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.776
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;

North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351

;
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PRISM
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.35
_refine_diff_density_max         1.069
_refine_diff_density_min         -0.728
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         4239
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.1151
_refine_ls_R_factor_gt           0.0844
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1469P)²+2.1033P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2414
_refine_ls_wR_factor_ref         0.2664
_reflns_number_gt                2843
_reflns_number_total             4239
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c2ce25846c.txt
_cod_data_source_block           per2fum1
_cod_original_cell_volume        2286(2)
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               7208579
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
C1 C 0.7371(7) 0.33843(19) 0.7408(7) 0.0651(14) Uani 1 1 d . A 1
H1 H 0.8232 0.3362 0.8419 0.078 Uiso 0.133(5) 1 d PR B 1
C2 C 0.6493(8) 0.37774(18) 0.6938(8) 0.0717(16) Uani 1 1 d . A 1
H2 H 0.6782 0.4020 0.7618 0.086 Uiso 1 1 calc R A 1
C3 C 0.5174(8) 0.38081(17) 0.5443(8) 0.0709(17) Uani 1 1 d . A 1
H3 H 0.4582 0.4073 0.5129 0.085 Uiso 1 1 calc R A 1
C4 C 0.4749(7) 0.34642(16) 0.4454(7) 0.0618(13) Uani 1 1 d U A 1
C5 C 0.5702(6) 0.30530(15) 0.4909(6) 0.0509(11) Uani 1 1 d U A 1
C6 C 0.6985(6) 0.30227(15) 0.6389(6) 0.0516(12) Uani 1 1 d . A 1
H6 H 0.7596 0.2761 0.6712 0.062 Uiso 1 1 calc R A 1
C7 C 0.4095(6) 0.32281(17) 0.1550(7) 0.0617(14) Uani 1 1 d . A 1
C8 C 0.3887(7) 0.3375(2) 0.0091(7) 0.0743(18) Uani 1 1 d . A 1
H8 H 0.3233 0.3623 -0.0359 0.089 Uiso 1 1 calc R A 1
C9 C 0.4643(8) 0.3155(3) -0.0710(8) 0.085(2) Uani 1 1 d . A 1
H9 H 0.4490 0.3250 -0.1703 0.102 Uiso 1 1 calc R A 1
C10 C 0.5591(7) 0.2806(2) -0.0026(7) 0.0746(16) Uani 1 1 d D A 1
H10 H 0.6094 0.2658 -0.0567 0.089 Uiso 0.867(5) 1 calc PR B 1
C11 C 0.5874(6) 0.26501(18) 0.1474(6) 0.0572(12) Uani 1 1 d . A 1
H11 H 0.6580 0.2411 0.1928 0.069 Uiso 1 1 calc R A 1
C12 C 0.5096(5) 0.28553(15) 0.2250(6) 0.0500(11) Uani 1 1 d . A 1
C13 C 0.5898(5) 0.22631(14) 0.4291(6) 0.0471(10) Uani 1 1 d . A 1
H13A H 0.7095 0.2267 0.4899 0.057 Uiso 1 1 calc R A 1
H13B H 0.5637 0.2078 0.3370 0.057 Uiso 1 1 calc R A 1
C14 C 0.5117(6) 0.20616(14) 0.5290(6) 0.0510(11) Uani 1 1 d . A 1
H14A H 0.5485 0.2226 0.6270 0.061 Uiso 1 1 calc R A 1
H14B H 0.3920 0.2089 0.4732 0.061 Uiso 1 1 calc R A 1
C15 C 0.5572(6) 0.15740(14) 0.5660(6) 0.0491(11) Uani 1 1 d . A 1
H15A H 0.6763 0.1551 0.6282 0.059 Uiso 1 1 calc R A 1
H15B H 0.5049 0.1463 0.6299 0.059 Uiso 1 1 calc R A 1
C16 C 0.3274(5) 0.12576(14) 0.3364(6) 0.0463(10) Uani 1 1 d . A 1
H16A H 0.2809 0.1553 0.3053 0.056 Uiso 1 1 calc R A 1
H16B H 0.2804 0.1129 0.4021 0.056 Uiso 1 1 calc R A 1
C17 C 0.2822(5) 0.09762(14) 0.1923(5) 0.0463(10) Uani 1 1 d . A 1
H17A H 0.1623 0.0954 0.1361 0.056 Uiso 1 1 calc R A 1
H17B H 0.3219 0.1118 0.1229 0.056 Uiso 1 1 calc R A 1
C18 C 0.5383(4) 0.05507(13) 0.3338(5) 0.0380(9) Uani 1 1 d . A 1
H18A H 0.5833 0.0256 0.3687 0.046 Uiso 1 1 calc R A 1
H18B H 0.5917 0.0674 0.2726 0.046 Uiso 1 1 calc R A 1
C19 C 0.5735(5) 0.08405(13) 0.4746(5) 0.0398(9) Uani 1 1 d . A 1
H19A H 0.5234 0.0710 0.5374 0.048 Uiso 1 1 calc R A 1
H19B H 0.6924 0.0855 0.5394 0.048 Uiso 1 1 calc R A 1
C20 C 0.3146(6) 0.02522(15) 0.0860(5) 0.0466(10) Uani 1 1 d . A 1
H20A H 0.1972 0.0282 0.0166 0.056 Uiso 1 1 calc R A 1
H20B H 0.3755 0.0374 0.0316 0.056 Uiso 1 1 calc R A 1
C21 C 0.3554(7) -0.02324(17) 0.1164(6) 0.0609(13) Uani 1 1 d . A 1
H21A H 0.4709 -0.0265 0.1913 0.073 Uiso 1 1 calc R A 1
H21B H 0.2878 -0.0363 0.1625 0.073 Uiso 1 1 calc R A 1
C22 C 0.0715(5) 0.01814(14) 0.3407(5) 0.0409(9) Uani 1 1 d . C 1
C23 C -0.0296(5) 0.00435(13) 0.4243(5) 0.0415(9) Uani 1 1 d . . 1
H23 H -0.1436 0.0017 0.3641 0.050 Uiso 1 1 calc R . 1
N1 N 0.5304(5) 0.27181(12) 0.3780(5) 0.0488(9) Uani 1 1 d . A 1
N2 N 0.5085(4) 0.12907(11) 0.4272(4) 0.0381(8) Uani 1 1 d . A 1
N3 N 0.3546(4) 0.05196(10) 0.2328(4) 0.0342(7) Uani 1 1 d D A 1
H3N H 0.306(5) 0.0383(13) 0.295(4) 0.041 Uiso 1 1 d D D 1
O1 O 0.3270(4) -0.04577(14) -0.0231(4) 0.0723(11) Uani 1 1 d D A 1
H1O H 0.211(2) -0.045(2) -0.094(5) 0.087 Uiso 1 1 d D E 1
O2 O -0.0024(4) 0.03181(15) 0.2033(4) 0.0678(11) Uani 1 1 d . C 1
O3 O 0.2283(4) 0.01632(11) 0.4161(4) 0.0544(9) Uani 1 1 d . C 1
S1 S 0.31084(17) 0.34949(5) 0.2564(2) 0.0699(5) Uani 1 1 d . A 1
Cl1A Cl 0.9060(2) 0.33507(7) 0.9216(2) 0.0809(7) Uani 0.867(5) 1 d P A 1
Cl1B Cl 0.617(2) 0.2501(5) -0.1078(18) 0.124(7) Uani 0.133(5) 1 d PDU B 2
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'
Cl Cl 0.1484 0.1585 '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'
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
C2 C1 C6 120.9(6) .
C2 C1 Cl1A 120.0(5) .
C6 C1 Cl1A 119.0(5) .
C1 C2 C3 119.6(5) .
C1 C2 H2 120.2 .
C3 C2 H2 120.2 .
C4 C3 C2 120.9(5) .
C4 C3 H3 119.5 .
C2 C3 H3 119.5 .
C3 C4 C5 120.1(6) .
C3 C4 S1 121.9(5) .
C5 C4 S1 118.0(4) .
C6 C5 N1 123.4(4) .
C6 C5 C4 118.7(4) .
N1 C5 C4 117.8(5) .
C5 C6 C1 119.7(5) .
C5 C6 H6 120.1 .
C1 C6 H6 120.1 .
C8 C7 C12 120.2(5) .
C8 C7 S1 121.1(4) .
C12 C7 S1 118.6(4) .
C7 C8 C9 120.5(6) .
C7 C8 H8 119.8 .
C9 C8 H8 119.8 .
C10 C9 C8 118.4(6) .
C10 C9 H9 120.8 .
C8 C9 H9 120.8 .
C9 C10 C11 123.3(7) .
C9 C10 H10 118.3 .
C11 C10 H10 118.3 .
C12 C11 C10 118.7(5) .
C12 C11 H11 120.6 .
C10 C11 H11 120.6 .
C11 C12 C7 118.8(5) .
C11 C12 N1 122.7(4) .
C7 C12 N1 118.5(5) .
N1 C13 C14 112.0(4) .
N1 C13 H13A 109.2 .
C14 C13 H13A 109.2 .
N1 C13 H13B 109.2 .
C14 C13 H13B 109.2 .
H13A C13 H13B 107.9 .
C15 C14 C13 112.1(4) .
C15 C14 H14A 109.2 .
C13 C14 H14A 109.2 .
C15 C14 H14B 109.2 .
C13 C14 H14B 109.2 .
H14A C14 H14B 107.9 .
N2 C15 C14 114.4(4) .
N2 C15 H15A 108.7 .
C14 C15 H15A 108.7 .
N2 C15 H15B 108.7 .
C14 C15 H15B 108.7 .
H15A C15 H15B 107.6 .
N2 C16 C17 111.0(3) .
N2 C16 H16A 109.4 .
C17 C16 H16A 109.4 .
N2 C16 H16B 109.4 .
C17 C16 H16B 109.4 .
H16A C16 H16B 108.0 .
N3 C17 C16 111.9(3) .
N3 C17 H17A 109.2 .
C16 C17 H17A 109.2 .
N3 C17 H17B 109.2 .
C16 C17 H17B 109.2 .
H17A C17 H17B 107.9 .
C19 C18 N3 110.2(3) .
C19 C18 H18A 109.6 .
N3 C18 H18A 109.6 .
C19 C18 H18B 109.6 .
N3 C18 H18B 109.6 .
H18A C18 H18B 108.1 .
N2 C19 C18 111.5(3) .
N2 C19 H19A 109.3 .
C18 C19 H19A 109.3 .
N2 C19 H19B 109.3 .
C18 C19 H19B 109.3 .
H19A C19 H19B 108.0 .
C21 C20 N3 113.9(4) .
C21 C20 H20A 108.8 .
N3 C20 H20A 108.8 .
C21 C20 H20B 108.8 .
N3 C20 H20B 108.8 .
H20A C20 H20B 107.7 .
O1 C21 C20 111.2(4) .
O1 C21 H21A 109.4 .
C20 C21 H21A 109.4 .
O1 C21 H21B 109.4 .
C20 C21 H21B 109.4 .
H21A C21 H21B 108.0 .
O2 C22 O3 123.6(4) .
O2 C22 C23 118.2(4) .
O3 C22 C23 118.1(4) .
C23 C23 C22 125.3(5) 3_556
C23 C23 H23 117.4 3_556
C22 C23 H23 117.4 .
C5 N1 C12 116.0(4) .
C5 N1 C13 119.1(4) .
C12 N1 C13 117.9(4) .
C15 N2 C19 110.1(3) .
C15 N2 C16 112.5(3) .
C19 N2 C16 107.8(3) .
C17 N3 C20 110.8(3) .
C17 N3 C18 109.7(3) .
C20 N3 C18 111.8(3) .
C17 N3 H3N 107(3) .
C20 N3 H3N 110(3) .
C18 N3 H3N 108(3) .
C21 O1 H1O 110(4) .
C4 S1 C7 97.5(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.382(8) .
C1 C6 1.391(7) .
C1 Cl1A 1.717(6) .
C2 C3 1.391(9) .
C2 H2 0.9300 .
C3 C4 1.332(7) .
C3 H3 0.9300 .
C4 C5 1.457(7) .
C4 S1 1.747(6) .
C5 C6 1.369(7) .
C5 N1 1.394(6) .
C6 H6 0.9300 .
C7 C8 1.377(8) .
C7 C12 1.407(7) .
C7 S1 1.755(6) .
C8 C9 1.383(10) .
C8 H8 0.9300 .
C9 C10 1.327(9) .
C9 H9 0.9300 .
C10 C11 1.404(8) .
C10 H10 0.9300 .
C11 C12 1.360(7) .
C11 H11 0.9300 .
C12 N1 1.432(6) .
C13 N1 1.472(5) .
C13 C14 1.523(6) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 C15 1.521(6) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 N2 1.459(6) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 N2 1.470(5) .
C16 C17 1.498(6) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 N3 1.495(5) .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C18 C19 1.501(6) .
C18 N3 1.502(5) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C19 N2 1.465(5) .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C20 C21 1.500(7) .
C20 N3 1.502(5) .
C20 H20A 0.9700 .
C20 H20B 0.9700 .
C21 O1 1.400(6) .
C21 H21A 0.9700 .
C21 H21B 0.9700 .
C22 O2 1.240(5) .
C22 O3 1.269(5) .
C22 C23 1.496(6) .
C23 C23 1.313(8) 3_556
C23 H23 0.9300 .
N3 H3N 0.958(10) .
O1 H1O 0.958(10) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 1.9(8) .
Cl1A C1 C2 C3 177.0(4) .
C1 C2 C3 C4 -0.3(8) .
C2 C3 C4 C5 -2.1(8) .
C2 C3 C4 S1 -179.5(4) .
C3 C4 C5 C6 2.8(7) .
S1 C4 C5 C6 -179.6(3) .
C3 C4 C5 N1 -174.1(4) .
S1 C4 C5 N1 3.4(6) .
N1 C5 C6 C1 175.6(4) .
C4 C5 C6 C1 -1.2(6) .
C2 C1 C6 C5 -1.1(7) .
Cl1A C1 C6 C5 -176.2(3) .
C12 C7 C8 C9 0.7(8) .
S1 C7 C8 C9 -178.6(4) .
C7 C8 C9 C10 -1.1(9) .
C8 C9 C10 C11 -0.4(9) .
C9 C10 C11 C12 2.3(8) .
C10 C11 C12 C7 -2.7(7) .
C10 C11 C12 N1 179.7(4) .
C8 C7 C12 C11 1.3(7) .
S1 C7 C12 C11 -179.4(4) .
C8 C7 C12 N1 179.0(4) .
S1 C7 C12 N1 -1.8(6) .
N1 C13 C14 C15 173.3(4) .
C13 C14 C15 N2 -58.7(5) .
N2 C16 C17 N3 57.5(5) .
N3 C18 C19 N2 -59.6(4) .
N3 C20 C21 O1 -175.6(4) .
O2 C22 C23 C23 -169.1(6) 3_556
O3 C22 C23 C23 9.0(8) 3_556
C6 C5 N1 C12 -130.3(4) .
C4 C5 N1 C12 46.5(5) .
C6 C5 N1 C13 19.7(6) .
C4 C5 N1 C13 -163.5(4) .
C11 C12 N1 C5 129.6(5) .
C7 C12 N1 C5 -48.0(5) .
C11 C12 N1 C13 -20.8(6) .
C7 C12 N1 C13 161.6(4) .
C14 C13 N1 C5 65.7(5) .
C14 C13 N1 C12 -144.8(4) .
C14 C15 N2 C19 173.8(3) .
C14 C15 N2 C16 -66.0(5) .
C18 C19 N2 C15 -175.0(3) .
C18 C19 N2 C16 61.9(4) .
C17 C16 N2 C15 178.2(3) .
C17 C16 N2 C19 -60.2(4) .
C16 C17 N3 C20 -177.1(3) .
C16 C17 N3 C18 -53.2(4) .
C21 C20 N3 C17 -169.3(4) .
C21 C20 N3 C18 67.9(5) .
C19 C18 N3 C17 53.6(4) .
C19 C18 N3 C20 176.9(3) .
C3 C4 S1 C7 136.3(4) .
C5 C4 S1 C7 -41.1(4) .
C8 C7 S1 C4 -140.4(4) .
C12 C7 S1 C4 40.4(4) .
