#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:18:17 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179659 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/12/4511237.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_4511237
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 H29 Cl F N O6'
_chemical_formula_weight         469.92
_chemical_name_common            'Haloperidol-fumaric acid salt dihydrate'
_chemical_name_systematic        'Haloperidol-fumaric acid salt dihydrate'
_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                97.42(3)
_cell_angle_beta                 98.87(3)
_cell_angle_gamma                114.92(3)
_cell_formula_units_Z            2
_cell_length_a                   8.7151(17)
_cell_length_b                   10.152(2)
_cell_length_c                   14.454(3)
_cell_measurement_reflns_used    4041
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      30.9831
_cell_measurement_theta_min      2.2661
_cell_volume                     1118.7(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 0.989
_diffrn_measured_fraction_theta_max 0.979
_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  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15849
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.46
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.9763
_exptl_absorpt_correction_T_min  0.9311
_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    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         5448
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0541P)²+0.5502P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1234
_reflns_number_gt                5056
_reflns_number_total             5448
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg500245e_si_003.cif
_cod_data_source_block           HAL-FUA
_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        1118.6(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4511237
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 1.27296(5) 0.44124(5) 1.05852(3) 0.03026(12) Uani 1 1 d .
O1 O 0.65482(14) 0.16095(13) 0.64739(8) 0.0241(2) Uani 1 1 d .
N1 N 0.81810(17) 0.15214(14) 0.44227(9) 0.0191(3) Uani 1 1 d .
C4 C 0.7241(2) 0.10308(17) 0.33809(10) 0.0214(3) Uani 1 1 d .
H4A H 0.7674 0.1891 0.3072 0.026 Uiso 1 1 calc R
H4B H 0.5986 0.0710 0.3337 0.026 Uiso 1 1 calc R
C10 C 0.94478(19) 0.27107(17) 0.75445(11) 0.0203(3) Uani 1 1 d .
O5 O 0.13176(18) 0.36521(15) 0.26194(10) 0.0349(3) Uani 1 1 d .
F1 F 0.4510(2) -0.30562(17) -0.28103(8) 0.0564(4) Uani 1 1 d .
C7 C 0.83588(18) 0.21507(17) 0.65101(11) 0.0201(3) Uani 1 1 d .
O2 O 0.88514(17) 0.08677(16) 0.12859(10) 0.0402(3) Uani 1 1 d .
C8 C 0.8563(2) 0.08324(17) 0.60050(10) 0.0208(3) Uani 1 1 d .
H8A H 0.9813 0.1132 0.6046 0.025 Uiso 1 1 calc R
H8B H 0.8123 0.0005 0.6342 0.025 Uiso 1 1 calc R
C15 C 1.1239(2) 0.31646(18) 0.77256(11) 0.0241(3) Uani 1 1 d .
H15 H 1.1771 0.3127 0.7203 0.029 Uiso 1 1 calc R
C6 C 0.8949(2) 0.33863(17) 0.59402(11) 0.0222(3) Uani 1 1 d .
H6A H 0.8754 0.4223 0.6232 0.027 Uiso 1 1 calc R
H6B H 1.0211 0.3763 0.5978 0.027 Uiso 1 1 calc R
C13 C 1.1469(2) 0.37310(18) 0.94162(11) 0.0233(3) Uani 1 1 d .
C1 C 0.7398(2) -0.01692(18) 0.10557(11) 0.0251(3) Uani 1 1 d .
C2 C 0.6389(2) -0.07602(18) 0.17925(11) 0.0235(3) Uani 1 1 d .
H2A H 0.5845 -0.1861 0.1624 0.028 Uiso 1 1 calc R
H2B H 0.5440 -0.0462 0.1755 0.028 Uiso 1 1 calc R
C5 C 0.7965(2) 0.28224(17) 0.48933(11) 0.0226(3) Uani 1 1 d .
H5A H 0.6714 0.2520 0.4853 0.027 Uiso 1 1 calc R
H5B H 0.8398 0.3636 0.4546 0.027 Uiso 1 1 calc R
C9 C 0.75893(19) 0.02852(16) 0.49544(10) 0.0204(3) Uani 1 1 d .
H9A H 0.7796 -0.0540 0.4655 0.024 Uiso 1 1 calc R
H9B H 0.6325 -0.0100 0.4910 0.024 Uiso 1 1 calc R
C14 C 1.2255(2) 0.36710(18) 0.86597(11) 0.0248(3) Uani 1 1 d .
H14 H 1.3470 0.3971 0.8776 0.030 Uiso 1 1 calc R
C3 C 0.7466(2) -0.02316(18) 0.28349(11) 0.0243(3) Uani 1 1 d .
H3A H 0.7099 -0.1075 0.3162 0.029 Uiso 1 1 calc R
H3B H 0.8711 0.0106 0.2836 0.029 Uiso 1 1 calc R
C16 C 0.6564(2) -0.09088(18) 0.00218(11) 0.0251(3) Uani 1 1 d .
C12 C 0.9703(2) 0.3298(2) 0.92568(12) 0.0284(3) Uani 1 1 d .
H12 H 0.9179 0.3350 0.9781 0.034 Uiso 1 1 calc R
C17 C 0.4822(2) -0.19468(19) -0.02885(12) 0.0290(3) Uani 1 1 d .
H17 H 0.4114 -0.2179 0.0163 0.035 Uiso 1 1 calc R
C11 C 0.8699(2) 0.2784(2) 0.83179(12) 0.0265(3) Uani 1 1 d .
H11 H 0.7484 0.2480 0.8206 0.032 Uiso 1 1 calc R
C21 C 0.7594(3) -0.0566(2) -0.06485(13) 0.0332(4) Uani 1 1 d .
H21 H 0.8775 0.0163 -0.0446 0.040 Uiso 1 1 calc R
C18 C 0.4104(3) -0.2649(2) -0.12520(13) 0.0355(4) Uani 1 1 d .
H18 H 0.2906 -0.3333 -0.1471 0.043 Uiso 1 1 calc R
C20 C 0.6902(3) -0.1283(3) -0.16050(13) 0.0410(5) Uani 1 1 d .
H20 H 0.7597 -0.1064 -0.2063 0.049 Uiso 1 1 calc R
C19 C 0.5186(3) -0.2320(2) -0.18746(12) 0.0383(5) Uani 1 1 d .
O3 O 0.71563(14) 0.68067(13) 0.42022(8) 0.0255(2) Uani 1 1 d .
O6 O 0.43157(17) 0.62562(14) 0.27846(9) 0.0278(3) Uani 1 1 d .
O4 O 0.85390(14) 0.74126(14) 0.57432(8) 0.0284(3) Uani 1 1 d .
C22 C 0.56233(19) 0.55942(17) 0.53132(11) 0.0210(3) Uani 1 1 d .
H22 H 0.5508 0.5764 0.5955 0.025 Uiso 1 1 calc R
C23 C 0.72006(19) 0.66763(17) 0.50499(11) 0.0216(3) Uani 1 1 d .
H2 H 0.935(3) 0.186(3) 0.4441(16) 0.040(6) Uiso 1 1 d .
H6 H 0.507(4) 0.628(3) 0.322(2) 0.053(7) Uiso 1 1 d .
H5 H 0.335(4) 0.536(3) 0.2684(18) 0.053(7) Uiso 1 1 d .
H4 H 0.142(4) 0.325(3) 0.312(2) 0.063(8) Uiso 1 1 d .
H3 H 0.072(3) 0.293(3) 0.213(2) 0.055(7) Uiso 1 1 d .
H1 H 0.635(4) 0.237(3) 0.673(2) 0.064(8) 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
C7 O1 H1 109.2(18) .
C9 N1 C5 110.60(12) .
C9 N1 C4 112.57(12) .
C5 N1 C4 109.84(12) .
C9 N1 H2 109.9(14) .
C5 N1 H2 106.8(14) .
C4 N1 H2 106.9(14) .
N1 C4 C3 113.48(12) .
N1 C4 H4A 108.9 .
C3 C4 H4A 108.9 .
N1 C4 H4B 108.9 .
C3 C4 H4B 108.9 .
H4A C4 H4B 107.7 .
C11 C10 C15 118.50(14) .
C11 C10 C7 121.52(13) .
C15 C10 C7 119.98(14) .
H4 O5 H3 107(2) .
O1 C7 C8 105.77(12) .
O1 C7 C10 111.75(12) .
C8 C7 C10 110.28(12) .
O1 C7 C6 110.02(12) .
C8 C7 C6 108.12(12) .
C10 C7 C6 110.73(12) .
C9 C8 C7 112.58(12) .
C9 C8 H8A 109.1 .
C7 C8 H8A 109.1 .
C9 C8 H8B 109.1 .
C7 C8 H8B 109.1 .
H8A C8 H8B 107.8 .
C14 C15 C10 121.05(15) .
C14 C15 H15 119.5 .
C10 C15 H15 119.5 .
C5 C6 C7 111.53(13) .
C5 C6 H6A 109.3 .
C7 C6 H6A 109.3 .
C5 C6 H6B 109.3 .
C7 C6 H6B 109.3 .
H6A C6 H6B 108.0 .
C12 C13 C14 121.07(15) .
C12 C13 Cl1 119.30(13) .
C14 C13 Cl1 119.60(12) .
O2 C1 C16 120.38(16) .
O2 C1 C2 121.63(15) .
C16 C1 C2 117.98(14) .
C1 C2 C3 115.14(13) .
C1 C2 H2A 108.5 .
C3 C2 H2A 108.5 .
C1 C2 H2B 108.5 .
C3 C2 H2B 108.5 .
H2A C2 H2B 107.5 .
N1 C5 C6 111.46(12) .
N1 C5 H5A 109.3 .
C6 C5 H5A 109.3 .
N1 C5 H5B 109.3 .
C6 C5 H5B 109.3 .
H5A C5 H5B 108.0 .
N1 C9 C8 110.80(12) .
N1 C9 H9A 109.5 .
C8 C9 H9A 109.5 .
N1 C9 H9B 109.5 .
C8 C9 H9B 109.5 .
H9A C9 H9B 108.1 .
C13 C14 C15 119.04(15) .
C13 C14 H14 120.5 .
C15 C14 H14 120.5 .
C4 C3 C2 111.54(13) .
C4 C3 H3A 109.3 .
C2 C3 H3A 109.3 .
C4 C3 H3B 109.3 .
C2 C3 H3B 109.3 .
H3A C3 H3B 108.0 .
C17 C16 C21 119.21(16) .
C17 C16 C1 122.37(15) .
C21 C16 C1 118.39(16) .
C13 C12 C11 119.28(15) .
C13 C12 H12 120.4 .
C11 C12 H12 120.4 .
C16 C17 C18 120.79(18) .
C16 C17 H17 119.6 .
C18 C17 H17 119.6 .
C10 C11 C12 121.05(15) .
C10 C11 H11 119.5 .
C12 C11 H11 119.5 .
C20 C21 C16 120.42(19) .
C20 C21 H21 119.8 .
C16 C21 H21 119.8 .
C19 C18 C17 117.74(19) .
C19 C18 H18 121.1 .
C17 C18 H18 121.1 .
C19 C20 C21 118.29(18) .
C19 C20 H20 120.9 .
C21 C20 H20 120.9 .
F1 C19 C20 118.55(19) .
F1 C19 C18 118.0(2) .
C20 C19 C18 123.46(17) .
H6 O6 H5 108(2) .
C22 C22 C23 122.74(18) 2_666
C22 C22 H22 118.6 2_666
C23 C22 H22 118.6 .
O3 C23 O4 124.38(15) .
O3 C23 C22 120.21(14) .
O4 C23 C22 115.41(14) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C13 1.7395(17) .
O1 C7 1.4251(18) .
O1 H1 0.90(3) .
N1 C9 1.5024(19) .
N1 C5 1.503(2) .
N1 C4 1.5061(19) .
N1 H2 0.92(2) .
C4 C3 1.517(2) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C10 C11 1.387(2) .
C10 C15 1.398(2) .
C10 C7 1.532(2) .
O5 H4 0.88(3) .
O5 H3 0.86(3) .
F1 C19 1.363(2) .
C7 C8 1.531(2) .
C7 C6 1.540(2) .
O2 C1 1.216(2) .
C8 C9 1.524(2) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C15 C14 1.393(2) .
C15 H15 0.9500 .
C6 C5 1.522(2) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C13 C12 1.381(2) .
C13 C14 1.385(2) .
C1 C16 1.497(2) .
C1 C2 1.509(2) .
C2 C3 1.539(2) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C14 H14 0.9500 .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C16 C17 1.391(3) .
C16 C21 1.399(2) .
C12 C11 1.395(2) .
C12 H12 0.9500 .
C17 C18 1.392(2) .
C17 H17 0.9500 .
C11 H11 0.9500 .
C21 C20 1.385(3) .
C21 H21 0.9500 .
C18 C19 1.373(3) .
C18 H18 0.9500 .
C20 C19 1.372(3) .
C20 H20 0.9500 .
O3 C23 1.2458(19) .
O6 H6 0.83(3) .
O6 H5 0.92(3) .
O4 C23 1.279(2) .
C22 C22 1.329(3) 2_666
C22 C23 1.496(2) .
C22 H22 0.9500 .
