#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:30:41 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179666 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/19/4511904.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_4511904
loop_
_publ_author_name
'Rajput, Lalit'
_publ_section_title
;
 Stable Crystalline Salts of Haloperidol: A Highly Water-Soluble Mesylate
 Salt
;
_journal_issue                   10
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5196
_journal_paper_doi               10.1021/cg500982u
_journal_volume                  14
_journal_year                    2014
_chemical_formula_sum            'C23 H29 Cl F N O9'
_chemical_formula_weight         517.92
_chemical_name_systematic
;
 ?
;
_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                106.846(7)
_cell_angle_beta                 100.623(7)
_cell_angle_gamma                102.977(7)
_cell_formula_units_Z            2
_cell_length_a                   10.9398(17)
_cell_length_b                   11.0705(17)
_cell_length_c                   11.7353(18)
_cell_measurement_reflns_used    11327
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      3.0
_cell_volume                     1277.2(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0419
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12666
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.119
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         5834
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.1165
_refine_ls_R_factor_gt           0.0980
_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)+(0.0636P)²+3.8827P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2288
_refine_ls_wR_factor_ref         0.2380
_reflns_number_gt                4609
_reflns_number_total             5834
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            cg500982u_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/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 

 Adding full bibliography for 4511904--4511913.cif.
;
_cod_original_cell_volume        1277.2(3)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4511904
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
C23 C 0.4450(4) 1.0327(4) 1.0091(3) 0.0253(8) Uani 1 1 d .
O5 O 0.4547(3) 1.1383(3) 0.9899(3) 0.0327(6) Uani 1 1 d .
O6 O 0.3548(3) 0.9718(3) 1.0420(3) 0.0332(6) Uani 1 1 d .
O7 O 0.3995(4) 1.3491(4) 1.1397(5) 0.067 Uani 1 1 d D
O8 O 0.5325(4) 1.4703(4) 1.3850(5) 0.0704(13) Uani 1 1 d D
O9 O 0.1563(5) 1.3818(5) 1.1469(8) 0.137(3) Uani 1 1 d .
H7B H 0.409(8) 1.279(8) 1.103(7) 0.11(3) Uiso 1 1 d .
H7A H 0.317(4) 1.328(14) 1.103(12) 0.231 Uiso 1 1 d D
H8C H 0.614(2) 1.499(5) 1.396(5) 0.049(15) Uiso 1 1 d D
H8D H 0.55(3) 1.409(19) 1.33(2) 0.49(17) Uiso 1 1 d D
H1N H 0.603(4) 1.222(5) 0.933(4) 0.029(12) Uiso 1 1 d .
H2A H 0.538(6) 1.373(6) 0.627(6) 0.06(2) Uiso 1 1 d .
C1 C 1.1341(4) 1.6410(4) 1.4348(4) 0.0314(8) Uani 1 1 d .
H1 H 1.1422 1.5977 1.3571 0.038 Uiso 1 1 calc R
C2 C 1.2450(5) 1.7087(5) 1.5321(4) 0.0411(10) Uani 1 1 d .
H2 H 1.3272 1.7112 1.5203 0.049 Uiso 1 1 calc R
C3 C 1.2309(5) 1.7718(5) 1.6457(4) 0.0430(11) Uani 1 1 d .
C4 C 1.1140(6) 1.7706(5) 1.6678(4) 0.0508(13) Uani 1 1 d .
H4 H 1.1082 1.8145 1.7463 0.061 Uiso 1 1 calc R
C5 C 1.0037(5) 1.7031(4) 1.5720(5) 0.0435(11) Uani 1 1 d .
H5 H 0.9225 1.7010 1.5864 0.052 Uiso 1 1 calc R
C6 C 1.0111(4) 1.6366(4) 1.4515(4) 0.0326(9) Uani 1 1 d .
C7 C 0.8905(4) 1.5654(4) 1.3519(5) 0.0413(10) Uani 1 1 d .
C8 C 0.8988(5) 1.5009(5) 1.2258(4) 0.0446(11) Uani 1 1 d .
H8A H 0.9517 1.4416 1.2281 0.053 Uiso 1 1 calc R
H8B H 0.9413 1.5676 1.1960 0.053 Uiso 1 1 calc R
C9 C 0.7645(5) 1.4226(5) 1.1361(4) 0.0473(11) Uani 1 1 d .
H9A H 0.7201 1.3574 1.1665 0.057 Uiso 1 1 calc R
H9B H 0.7124 1.4819 1.1300 0.057 Uiso 1 1 calc R
C10 C 0.7798(4) 1.3559(5) 1.0127(4) 0.0441(11) Uani 1 1 d .
H10A H 0.8311 1.2962 1.0202 0.053 Uiso 1 1 calc R
H10B H 0.8279 1.4220 0.9853 0.053 Uiso 1 1 calc R
C11 C 0.6854(4) 1.2127(4) 0.7997(4) 0.0334(9) Uani 1 1 d .
H11A H 0.7332 1.1521 0.8140 0.040 Uiso 1 1 calc R
H11B H 0.7411 1.2787 0.7776 0.040 Uiso 1 1 calc R
C12 C 0.5642(4) 1.1373(4) 0.6934(4) 0.0316(9) Uani 1 1 d .
H12A H 0.5118 1.0664 0.7124 0.038 Uiso 1 1 calc R
H12B H 0.5893 1.0981 0.6194 0.038 Uiso 1 1 calc R
C13 C 0.4835(4) 1.2280(4) 0.6697(3) 0.0263(8) Uani 1 1 d .
C14 C 0.4486(4) 1.2918(4) 0.7895(3) 0.0274(8) Uani 1 1 d .
H14A H 0.4001 1.3524 0.7769 0.033 Uiso 1 1 calc R
H14B H 0.3934 1.2237 0.8097 0.033 Uiso 1 1 calc R
C15 C 0.5696(4) 1.3659(4) 0.8961(4) 0.0299(8) Uani 1 1 d .
H15A H 0.6199 1.4400 0.8797 0.036 Uiso 1 1 calc R
H15B H 0.5440 1.4008 0.9709 0.036 Uiso 1 1 calc R
C16 C 0.3615(4) 1.1504(4) 0.5640(3) 0.0283(8) Uani 1 1 d .
C17 C 0.3453(4) 1.1699(4) 0.4502(4) 0.0322(9) Uani 1 1 d .
H17 H 0.4098 1.2330 0.4394 0.039 Uiso 1 1 calc R
C18 C 0.2349(4) 1.0971(4) 0.3531(4) 0.0356(9) Uani 1 1 d .
H18 H 0.2255 1.1106 0.2778 0.043 Uiso 1 1 calc R
C19 C 0.1395(4) 1.0043(4) 0.3704(4) 0.0340(9) Uani 1 1 d .
C20 C 0.1519(5) 0.9838(4) 0.4811(4) 0.0402(10) Uani 1 1 d .
H20 H 0.0865 0.9213 0.4915 0.048 Uiso 1 1 calc R
C21 C 0.2624(4) 1.0565(4) 0.5774(4) 0.0366(10) Uani 1 1 d .
H21 H 0.2704 1.0423 0.6524 0.044 Uiso 1 1 calc R
C22 C -0.0588(4) 1.0268(4) 0.0059(3) 0.0273(8) Uani 1 1 d .
N1 N 0.6533(3) 1.2791(3) 0.9161(3) 0.0287(7) Uani 1 1 d .
O1 O 0.7849(3) 1.5591(4) 1.3755(4) 0.0640(11) Uani 1 1 d .
O2 O 0.5663(3) 1.3263(3) 0.6410(3) 0.0342(7) Uani 1 1 d .
O3 O -0.1683(3) 0.9354(3) -0.0457(3) 0.0341(7) Uani 1 1 d .
H3 H -0.2282 0.9676 -0.0375 0.051 Uiso 1 1 calc R
O4 O -0.0442(3) 1.1424(3) 0.0582(3) 0.0390(7) Uani 1 1 d .
F1 F 1.3403(4) 1.8389(3) 1.7403(3) 0.0685(10) Uani 1 1 d .
Cl1 Cl 0.00142(12) 0.91007(12) 0.24817(10) 0.0475(3) 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'
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_3
O5 C23 O6 126.7(3) .
O5 C23 C23 117.6(4) 2_677
O6 C23 C23 115.7(4) 2_677
C2 C1 C6 121.1(4) .
C3 C2 C1 118.6(4) .
C4 C3 F1 118.8(4) .
C4 C3 C2 123.1(5) .
F1 C3 C2 118.1(5) .
C3 C4 C5 118.7(4) .
C4 C5 C6 121.3(4) .
C1 C6 C5 117.3(4) .
C1 C6 C7 123.2(4) .
C5 C6 C7 119.5(4) .
O1 C7 C6 119.4(5) .
O1 C7 C8 121.3(5) .
C6 C7 C8 119.3(4) .
C7 C8 C9 112.2(4) .
C10 C9 C8 109.6(4) .
C9 C10 N1 114.1(4) .
N1 C11 C12 112.0(3) .
C11 C12 C13 111.2(3) .
O2 C13 C16 111.6(3) .
O2 C13 C12 105.4(3) .
C16 C13 C12 110.4(3) .
O2 C13 C14 109.7(3) .
C16 C13 C14 111.1(3) .
C12 C13 C14 108.3(3) .
C15 C14 C13 111.3(3) .
N1 C15 C14 112.1(3) .
C21 C16 C17 117.8(4) .
C21 C16 C13 120.7(3) .
C17 C16 C13 121.5(4) .
C18 C17 C16 121.4(4) .
C19 C18 C17 118.8(4) .
C20 C19 C18 121.2(4) .
C20 C19 Cl1 119.6(4) .
C18 C19 Cl1 119.3(3) .
C19 C20 C21 119.7(4) .
C20 C21 C16 121.2(4) .
O4 C22 O3 126.2(3) .
O4 C22 C22 121.4(5) 2_575
O3 C22 C22 112.4(4) 2_575
C11 N1 C10 107.4(3) .
C11 N1 C15 111.4(3) .
C10 N1 C15 112.0(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C23 O5 1.239(5) .
C23 O6 1.253(5) .
C23 C23 1.554(7) 2_677
C1 C2 1.386(6) .
C1 C6 1.387(6) .
C2 C3 1.370(6) .
C3 C4 1.349(8) .
C3 F1 1.359(5) .
C4 C5 1.373(7) .
C5 C6 1.419(6) .
C6 C7 1.469(6) .
C7 O1 1.229(6) .
C7 C8 1.473(7) .
C8 C9 1.532(6) .
C9 C10 1.481(7) .
C10 N1 1.503(5) .
C11 N1 1.496(5) .
C11 C12 1.517(6) .
C12 C13 1.529(5) .
C13 O2 1.414(5) .
C13 C16 1.522(5) .
C13 C14 1.538(5) .
C14 C15 1.516(5) .
C15 N1 1.504(5) .
C16 C21 1.390(6) .
C16 C17 1.399(5) .
C17 C18 1.389(6) .
C18 C19 1.379(6) .
C19 C20 1.370(6) .
C19 Cl1 1.748(4) .
C20 C21 1.385(6) .
C22 O4 1.207(5) .
C22 O3 1.288(5) .
C22 C22 1.545(7) 2_575
