#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:18:17 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179659 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/12/4511238.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_4511238
loop_
_publ_author_name
'Aitipamula, Srinivasulu'
'Wong, Annie B. H.'
'Chow, Pui Shan'
'Tan, Reginald B. H.'
_publ_section_title
;
 Pharmaceutical Salts of Haloperidol with Some Carboxylic Acids and
 Artificial Sweeteners: Hydrate Formation, Polymorphism, and
 Physicochemical Properties
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2542
_journal_paper_doi               10.1021/cg500245e
_journal_volume                  14
_journal_year                    2014
_chemical_formula_sum            'C23 H30 Cl F N O6'
_chemical_formula_weight         470.93
_chemical_name_common            'Haloperidol-succinic acid salt hydrate'
_chemical_name_systematic        'Haloperidol-succinic acid salt hydrate'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                108.39(3)
_cell_angle_beta                 101.96(3)
_cell_angle_gamma                99.31(3)
_cell_formula_units_Z            2
_cell_length_a                   8.6026(17)
_cell_length_b                   10.585(2)
_cell_length_c                   13.862(3)
_cell_measurement_reflns_used    3740
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      31.0879
_cell_measurement_theta_min      2.0912
_cell_volume                     1136.2(5)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD area detector'
_diffrn_measurement_method       'ω 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  0.0509
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15621
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.61
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  0.9540
_exptl_absorpt_correction_T_min  0.9109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'R. H. Blessing, Acta Cryst. 1995 A51, 33-38'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             498
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.665
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         5520
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0587
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0943P)²+0.2923P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1623
_refine_ls_wR_factor_ref         0.1650
_reflns_number_gt                5270
_reflns_number_total             5520
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg500245e_si_003.cif
_cod_data_source_block           Hal-SUA
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        1136.2(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4511238
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Cl1 Cl 0.80057(5) 0.04535(4) -0.56530(3) 0.03279(14) Uani 1 1 d .
O1 O 0.48711(13) 0.32803(11) -0.16733(9) 0.0231(2) Uani 1 1 d .
F1 F 0.60194(13) 0.75498(11) 0.79333(8) 0.0364(3) Uani 1 1 d .
N1 N 0.73964(15) 0.37219(12) 0.08171(9) 0.0197(2) Uani 1 1 d .
O5 O 0.21680(14) 0.14007(13) 0.81436(10) 0.0288(3) Uani 1 1 d .
O2 O 0.81551(16) 0.39772(12) 0.41021(9) 0.0317(3) Uani 1 1 d .
C14 C 0.85676(19) 0.11896(16) -0.35278(12) 0.0245(3) Uani 1 1 d .
H14 H 0.9548 0.0887 -0.3531 0.029 Uiso 1 1 calc R
C4 C 0.72488(18) 0.43569(15) 0.19205(11) 0.0219(3) Uani 1 1 d .
H4A H 0.6834 0.3621 0.2167 0.026 Uiso 1 1 calc R
H4B H 0.6447 0.4930 0.1912 0.026 Uiso 1 1 calc R
C13 C 0.75123(19) 0.11051(15) -0.44646(12) 0.0247(3) Uani 1 1 d .
C10 C 0.67239(17) 0.21754(14) -0.25662(11) 0.0204(3) Uani 1 1 d .
C7 C 0.63442(17) 0.28268(14) -0.15145(11) 0.0201(3) Uani 1 1 d .
C15 C 0.81650(18) 0.17239(15) -0.25861(12) 0.0229(3) Uani 1 1 d .
H15 H 0.8881 0.1785 -0.1943 0.028 Uiso 1 1 calc R
C5 C 0.74844(18) 0.47434(14) 0.02745(11) 0.0209(3) Uani 1 1 d .
H5A H 0.8407 0.5551 0.0707 0.025 Uiso 1 1 calc R
H5B H 0.6460 0.5060 0.0204 0.025 Uiso 1 1 calc R
C8 C 0.62225(18) 0.18168(14) -0.09252(11) 0.0211(3) Uani 1 1 d .
H8A H 0.5281 0.1020 -0.1346 0.025 Uiso 1 1 calc R
H8B H 0.7229 0.1474 -0.0856 0.025 Uiso 1 1 calc R
C6 C 0.77257(17) 0.41052(14) -0.08149(11) 0.0210(3) Uani 1 1 d .
H6A H 0.8789 0.3848 -0.0738 0.025 Uiso 1 1 calc R
H6B H 0.7762 0.4791 -0.1163 0.025 Uiso 1 1 calc R
C19 C 0.65356(19) 0.69884(17) 0.70692(12) 0.0277(3) Uani 1 1 d .
C11 C 0.56822(18) 0.20677(15) -0.35211(12) 0.0238(3) Uani 1 1 d .
H11 H 0.4696 0.2362 -0.3524 0.029 Uiso 1 1 calc R
C9 C 0.60065(18) 0.24834(14) 0.01715(11) 0.0215(3) Uani 1 1 d .
H9A H 0.4955 0.2760 0.0104 0.026 Uiso 1 1 calc R
H9B H 0.5973 0.1813 0.0533 0.026 Uiso 1 1 calc R
C2 C 0.8678(2) 0.60521(16) 0.37543(12) 0.0282(3) Uani 1 1 d .
H2A H 0.9732 0.6716 0.4191 0.034 Uiso 1 1 calc R
H2B H 0.7859 0.6586 0.3638 0.034 Uiso 1 1 calc R
C12 C 0.60736(19) 0.15333(15) -0.44702(12) 0.0250(3) Uani 1 1 d .
H12 H 0.5358 0.1463 -0.5117 0.030 Uiso 1 1 calc R
C1 C 0.81391(19) 0.51897(16) 0.43667(12) 0.0243(3) Uani 1 1 d .
C3 C 0.88904(19) 0.52399(16) 0.26867(12) 0.0268(3) Uani 1 1 d .
H3A H 0.9390 0.5883 0.2386 0.032 Uiso 1 1 calc R
H3B H 0.9640 0.4645 0.2785 0.032 Uiso 1 1 calc R
C16 C 0.75969(18) 0.58616(15) 0.53208(11) 0.0237(3) Uani 1 1 d .
C20 C 0.6453(2) 0.56027(18) 0.67239(13) 0.0298(3) Uani 1 1 d .
H20 H 0.6038 0.5045 0.7077 0.036 Uiso 1 1 calc R
C18 C 0.7127(2) 0.78369(17) 0.65814(13) 0.0296(3) Uani 1 1 d .
H18 H 0.7167 0.8790 0.6842 0.035 Uiso 1 1 calc R
C17 C 0.7664(2) 0.72655(16) 0.56984(12) 0.0268(3) Uani 1 1 d .
H17 H 0.8077 0.7831 0.5350 0.032 Uiso 1 1 calc R
C21 C 0.6995(2) 0.50464(16) 0.58451(12) 0.0277(3) Uani 1 1 d .
H21 H 0.6957 0.4094 0.5595 0.033 Uiso 1 1 calc R
O4 O -0.01447(14) 0.25348(11) 0.11447(8) 0.0256(2) Uani 1 1 d .
O3 O 0.08947(15) 0.24561(11) -0.02104(9) 0.0274(2) Uani 1 1 d .
O6 O 0.8154(2) 0.13886(14) 0.22545(11) 0.0392(3) Uani 1 1 d .
C22 C 0.05190(17) 0.19608(14) 0.04439(11) 0.0205(3) Uani 1 1 d .
C23 C 0.07775(17) 0.05506(14) 0.03688(11) 0.0218(3) Uani 1 1 d .
H23A H 0.1009 0.0489 0.1080 0.026 Uiso 1 1 calc R
H23B H 0.1727 0.0399 0.0087 0.026 Uiso 1 1 calc R
H2 H 0.834(3) 0.342(2) 0.0851(17) 0.033(5) Uiso 1 1 d .
H4 H 0.206(3) 0.054(3) 0.7982(19) 0.041(6) Uiso 1 1 d .
H3 H 0.177(3) 0.167(3) 0.865(2) 0.044(6) Uiso 1 1 d .
H6 H 0.881(4) 0.167(3) 0.195(2) 0.070(9) Uiso 1 1 d .
H5 H 0.816(4) 0.198(3) 0.280(3) 0.074(10) Uiso 1 1 d .
H1 H 0.401(3) 0.260(3) -0.178(2) 0.053(7) Uiso 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'
F F 0.0171 0.0103 '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
C7 O1 H1 109.6(17) . .
C5 N1 C9 110.46(11) . .
C5 N1 C4 111.44(11) . .
C9 N1 C4 111.16(11) . .
C5 N1 H2 107.9(14) . .
C9 N1 H2 106.6(14) . .
C4 N1 H2 109.2(13) . .
H4 O5 H3 107(2) . .
C15 C14 C13 118.89(14) . .
C15 C14 H14 120.6 . .
C13 C14 H14 120.6 . .
N1 C4 C3 111.56(12) . .
N1 C4 H4A 109.3 . .
C3 C4 H4A 109.3 . .
N1 C4 H4B 109.3 . .
C3 C4 H4B 109.3 . .
H4A C4 H4B 108.0 . .
C12 C13 C14 121.06(14) . .
C12 C13 Cl1 119.35(12) . .
C14 C13 Cl1 119.59(12) . .
C11 C10 C15 118.45(13) . .
C11 C10 C7 120.99(12) . .
C15 C10 C7 120.50(13) . .
O1 C7 C10 111.10(11) . .
O1 C7 C6 106.69(11) . .
C10 C7 C6 109.14(11) . .
O1 C7 C8 110.24(11) . .
C10 C7 C8 110.99(11) . .
C6 C7 C8 108.56(11) . .
C14 C15 C10 121.32(14) . .
C14 C15 H15 119.3 . .
C10 C15 H15 119.3 . .
N1 C5 C6 110.64(11) . .
N1 C5 H5A 109.5 . .
C6 C5 H5A 109.5 . .
N1 C5 H5B 109.5 . .
C6 C5 H5B 109.5 . .
H5A C5 H5B 108.1 . .
C9 C8 C7 112.07(11) . .
C9 C8 H8A 109.2 . .
C7 C8 H8A 109.2 . .
C9 C8 H8B 109.2 . .
C7 C8 H8B 109.2 . .
H8A C8 H8B 107.9 . .
C5 C6 C7 111.76(12) . .
C5 C6 H6A 109.3 . .
C7 C6 H6A 109.3 . .
C5 C6 H6B 109.3 . .
C7 C6 H6B 109.3 . .
H6A C6 H6B 107.9 . .
F1 C19 C20 118.60(14) . .
F1 C19 C18 118.33(15) . .
C20 C19 C18 123.07(15) . .
C12 C11 C10 120.72(14) . .
C12 C11 H11 119.6 . .
C10 C11 H11 119.6 . .
N1 C9 C8 110.31(11) . .
N1 C9 H9A 109.6 . .
C8 C9 H9A 109.6 . .
N1 C9 H9B 109.6 . .
C8 C9 H9B 109.6 . .
H9A C9 H9B 108.1 . .
C1 C2 C3 114.74(13) . .
C1 C2 H2A 108.6 . .
C3 C2 H2A 108.6 . .
C1 C2 H2B 108.6 . .
C3 C2 H2B 108.6 . .
H2A C2 H2B 107.6 . .
C13 C12 C11 119.55(14) . .
C13 C12 H12 120.2 . .
C11 C12 H12 120.2 . .
O2 C1 C16 120.34(14) . .
O2 C1 C2 121.33(14) . .
C16 C1 C2 118.32(13) . .
C4 C3 C2 110.96(13) . .
C4 C3 H3A 109.4 . .
C2 C3 H3A 109.4 . .
C4 C3 H3B 109.4 . .
C2 C3 H3B 109.4 . .
H3A C3 H3B 108.0 . .
C21 C16 C17 119.14(14) . .
C21 C16 C1 118.36(13) . .
C17 C16 C1 122.51(14) . .
C19 C20 C21 117.92(14) . .
C19 C20 H20 121.0 . .
C21 C20 H20 121.0 . .
C19 C18 C17 118.45(15) . .
C19 C18 H18 120.8 . .
C17 C18 H18 120.8 . .
C18 C17 C16 120.26(14) . .
C18 C17 H17 119.9 . .
C16 C17 H17 119.9 . .
C20 C21 C16 121.16(14) . .
C20 C21 H21 119.4 . .
C16 C21 H21 119.4 . .
H6 O6 H5 113(3) . .
O3 C22 O4 124.07(13) . .
O3 C22 C23 118.86(13) . .
O4 C22 C23 116.98(12) . .
C22 C23 C23 109.13(14) . 2
C22 C23 H23A 109.9 . .
C23 C23 H23A 109.9 2 .
C22 C23 H23B 109.9 . .
C23 C23 H23B 109.9 2 .
H23A C23 H23B 108.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C13 1.7429(16) .
O1 C7 1.4257(16) .
O1 H1 0.90(3) .
F1 C19 1.3572(18) .
N1 C5 1.5003(17) .
N1 C9 1.503(2) .
N1 C4 1.5057(18) .
N1 H2 0.92(2) .
O5 H4 0.85(3) .
O5 H3 0.83(3) .
O2 C1 1.2218(19) .
C14 C15 1.389(2) .
C14 C13 1.389(2) .
C14 H14 0.9500 .
C4 C3 1.523(2) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C13 C12 1.385(2) .
C10 C11 1.396(2) .
C10 C15 1.4013(19) .
C10 C7 1.5309(19) .
C7 C6 1.535(2) .
C7 C8 1.5399(19) .
C15 H15 0.9500 .
C5 C6 1.5204(19) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C8 C9 1.5252(19) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C19 C20 1.377(2) .
C19 C18 1.379(2) .
C11 C12 1.393(2) .
C11 H11 0.9500 .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C2 C1 1.511(2) .
C2 C3 1.524(2) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C12 H12 0.9500 .
C1 C16 1.497(2) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C16 C21 1.396(2) .
C16 C17 1.398(2) .
C20 C21 1.386(2) .
C20 H20 0.9500 .
C18 C17 1.391(2) .
C18 H18 0.9500 .
C17 H17 0.9500 .
C21 H21 0.9500 .
O4 C22 1.2684(18) .
O3 C22 1.2524(18) .
O6 H6 0.84(3) .
O6 H5 0.82(3) .
C22 C23 1.5190(19) .
C23 C23 1.539(3) 2
C23 H23A 0.9900 .
C23 H23B 0.9900 .
