#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:30:41 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179666 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/19/4511908.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_4511908
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            'C38 H35 Cl F N O9'
_chemical_formula_weight         704.12
_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                70.835(5)
_cell_angle_beta                 80.524(6)
_cell_angle_gamma                74.251(5)
_cell_formula_units_Z            2
_cell_length_a                   8.1733(9)
_cell_length_b                   14.5646(16)
_cell_length_c                   15.5899(17)
_cell_measurement_reflns_used    7699
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.7
_cell_measurement_theta_min      3.0
_cell_volume                     1681.3(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  Rigaku
_diffrn_measurement_method       'profile data from 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  0.0586
_diffrn_reflns_av_sigmaI/netI    0.0771
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17944
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.574
_refine_diff_density_min         -0.711
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     455
_refine_ls_number_reflns         7699
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1146
_refine_ls_R_factor_gt           0.0697
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0706P)²+1.5129P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1569
_refine_ls_wR_factor_ref         0.1797
_reflns_number_gt                4952
_reflns_number_total             7699
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            cg500982u_si_002.cif
_cod_data_source_block           4-EA
_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_sg_symbol_H-M      P-1
_cod_database_code               4511908
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
C41 C 0.9632(18) 0.0476(5) -0.0055(6) 0.191(7) Uani 1 1 d .
C42 C 0.9220(17) 0.1204(9) -0.0869(9) 0.197(6) Uani 1 1 d .
C43 C 0.2223(14) 0.8927(6) 0.0822(6) 0.140(3) Uani 1 1 d .
O9 O 0.9543(10) 0.0458(7) 0.0561(4) 0.199(4) Uani 1 1 d .
H1N H 1.070(5) 0.220(3) 0.245(2) 0.035(10) Uiso 1 1 d .
Cl1 Cl 0.64891(16) 0.84839(6) 0.05209(6) 0.0518(3) Uani 1 1 d .
O2 O 0.6738(2) 0.37187(14) 0.09231(13) 0.0221(4) Uani 1 1 d .
H2 H 0.5748 0.3906 0.1115 0.033 Uiso 1 1 calc R
F1 F 1.7301(2) -0.50602(13) 0.46544(14) 0.0383(5) Uani 1 1 d .
N1 N 1.0071(3) 0.20046(16) 0.21681(16) 0.0184(5) Uani 1 1 d .
O1 O 1.2004(3) -0.11377(15) 0.49769(14) 0.0320(5) Uani 1 1 d .
C16 C 0.7458(3) 0.5131(2) 0.11706(18) 0.0191(6) Uani 1 1 d .
C17 C 0.6357(4) 0.5762(2) 0.05183(19) 0.0205(6) Uani 1 1 d .
H17 H 0.5831 0.5490 0.0208 0.025 Uiso 1 1 calc R
C18 C 0.6030(4) 0.6793(2) 0.03225(19) 0.0254(7) Uani 1 1 d .
H18 H 0.5276 0.7210 -0.0108 0.030 Uiso 1 1 calc R
C7 C 1.2580(4) -0.1391(2) 0.4298(2) 0.0230(6) Uani 1 1 d .
C13 C 0.7853(3) 0.3995(2) 0.13592(18) 0.0186(6) Uani 1 1 d .
C9 C 1.1050(4) 0.03248(19) 0.33348(19) 0.0212(6) Uani 1 1 d .
H9A H 0.9992 0.0302 0.3720 0.025 Uiso 1 1 calc R
H9B H 1.1706 0.0654 0.3553 0.025 Uiso 1 1 calc R
C8 C 1.2061(4) -0.0731(2) 0.33673(19) 0.0226(6) Uani 1 1 d .
H8A H 1.1380 -0.1046 0.3148 0.027 Uiso 1 1 calc R
H8B H 1.3081 -0.0688 0.2953 0.027 Uiso 1 1 calc R
C21 C 0.8260(4) 0.5558(2) 0.1610(2) 0.0262(7) Uani 1 1 d .
H21 H 0.9015 0.5146 0.2042 0.031 Uiso 1 1 calc R
C14 C 0.9659(4) 0.3640(2) 0.09441(19) 0.0202(6) Uani 1 1 d .
H14A H 0.9702 0.3938 0.0288 0.024 Uiso 1 1 calc R
H14B H 1.0459 0.3868 0.1175 0.024 Uiso 1 1 calc R
C19 C 0.6844(4) 0.7188(2) 0.0778(2) 0.0283(7) Uani 1 1 d .
C6 C 1.3839(4) -0.2366(2) 0.4360(2) 0.0212(6) Uani 1 1 d .
C15 C 1.0195(4) 0.2512(2) 0.11631(18) 0.0225(6) Uani 1 1 d .
H15A H 0.9472 0.2290 0.0875 0.027 Uiso 1 1 calc R
H15B H 1.1361 0.2322 0.0914 0.027 Uiso 1 1 calc R
C11 C 0.8302(4) 0.2312(2) 0.25805(19) 0.0217(6) Uani 1 1 d .
H11A H 0.8258 0.1995 0.3234 0.026 Uiso 1 1 calc R
H11B H 0.7517 0.2089 0.2334 0.026 Uiso 1 1 calc R
C10 C 1.0676(4) 0.08956(19) 0.23520(19) 0.0222(6) Uani 1 1 d .
H10A H 1.1704 0.0757 0.1959 0.027 Uiso 1 1 calc R
H10B H 0.9815 0.0649 0.2192 0.027 Uiso 1 1 calc R
C4 C 1.5546(4) -0.3870(2) 0.5318(2) 0.0318(7) Uani 1 1 d .
H4 H 1.5896 -0.4267 0.5889 0.038 Uiso 1 1 calc R
C12 C 0.7754(4) 0.3446(2) 0.23833(18) 0.0198(6) Uani 1 1 d .
H12A H 0.8483 0.3659 0.2675 0.024 Uiso 1 1 calc R
H12B H 0.6593 0.3626 0.2642 0.024 Uiso 1 1 calc R
C1 C 1.4477(4) -0.2708(2) 0.3613(2) 0.0298(7) Uani 1 1 d .
H1 H 1.4118 -0.2325 0.3040 0.036 Uiso 1 1 calc R
C20 C 0.7956(4) 0.6580(2) 0.1418(2) 0.0299(7) Uani 1 1 d .
H20 H 0.8498 0.6856 0.1718 0.036 Uiso 1 1 calc R
C3 C 1.6155(4) -0.4169(2) 0.4557(2) 0.0281(7) Uani 1 1 d .
C5 C 1.4392(4) -0.2955(2) 0.5209(2) 0.0280(7) Uani 1 1 d .
H5 H 1.3978 -0.2730 0.5715 0.034 Uiso 1 1 calc R
C2 C 1.5655(4) -0.3624(2) 0.3713(2) 0.0321(7) Uani 1 1 d .
H2A H 1.6087 -0.3856 0.3213 0.039 Uiso 1 1 calc R
O4 O 0.3817(2) 0.31897(14) 0.19730(13) 0.0220(4) Uani 1 1 d .
O3 O 0.1760(2) 0.27687(13) 0.30437(13) 0.0208(4) Uani 1 1 d .
C23 C 0.2222(3) 0.43916(19) 0.27040(19) 0.0181(6) Uani 1 1 d .
O5 O 0.0999(3) 0.72421(15) 0.29576(17) 0.0396(6) Uani 1 1 d .
H5A H 0.0313 0.7281 0.3399 0.059 Uiso 1 1 calc R
C28 C 0.1077(3) 0.4607(2) 0.34138(19) 0.0193(6) Uani 1 1 d .
H28 H 0.0581 0.4110 0.3821 0.023 Uiso 1 1 calc R
C22 C 0.2644(3) 0.33866(19) 0.25646(18) 0.0174(6) Uani 1 1 d .
C27 C 0.0662(4) 0.5549(2) 0.35241(19) 0.0210(6) Uani 1 1 d .
H27 H -0.0102 0.5685 0.4004 0.025 Uiso 1 1 calc R
C26 C 0.1402(4) 0.6296(2) 0.2907(2) 0.0274(7) Uani 1 1 d .
C24 C 0.2954(4) 0.5141(2) 0.2100(2) 0.0287(7) Uani 1 1 d .
H24 H 0.3724 0.5006 0.1623 0.034 Uiso 1 1 calc R
C25 C 0.2553(4) 0.6082(2) 0.2202(2) 0.0371(8) Uani 1 1 d .
H25 H 0.3057 0.6576 0.1796 0.045 Uiso 1 1 calc R
O8 O 0.4722(3) 0.14289(15) 0.16970(14) 0.0298(5) Uani 1 1 d .
H8 H 0.4256 0.1917 0.1873 0.045 Uiso 1 1 calc R
O6 O 0.8965(3) -0.25019(14) 0.44257(15) 0.0297(5) Uani 1 1 d .
O7 O 0.7504(3) -0.15913(15) 0.53217(13) 0.0281(5) Uani 1 1 d .
H7 H 0.7978 -0.2075 0.5717 0.042 Uiso 1 1 calc R
C29 C 0.7972(4) -0.1742(2) 0.4519(2) 0.0216(6) Uani 1 1 d .
C30 C 0.7165(4) -0.0894(2) 0.37707(19) 0.0204(6) Uani 1 1 d .
C35 C 0.6300(3) 0.00153(19) 0.39244(19) 0.0187(6) Uani 1 1 d .
H35 H 0.6275 0.0094 0.4495 0.022 Uiso 1 1 calc R
C34 C 0.5490(4) 0.0791(2) 0.32455(19) 0.0196(6) Uani 1 1 d .
H34 H 0.4922 0.1391 0.3359 0.024 Uiso 1 1 calc R
C31 C 0.7189(4) -0.0991(2) 0.2908(2) 0.0240(6) Uani 1 1 d .
H31 H 0.7757 -0.1590 0.2793 0.029 Uiso 1 1 calc R
C32 C 0.6380(4) -0.0210(2) 0.2225(2) 0.0269(7) Uani 1 1 d .
H32 H 0.6417 -0.0285 0.1652 0.032 Uiso 1 1 calc R
C33 C 0.5509(4) 0.0689(2) 0.23834(19) 0.0220(6) 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_1
_geom_angle_site_symmetry_3
O9 C41 C41 97.7(13) . 2_755
O9 C41 C42 135.8(11) . .
C41 C41 C42 126.5(12) 2_755 .
O9 C41 O9 130.6(10) . 2_755
C41 C41 O9 32.9(5) 2_755 2_755
C42 C41 O9 93.7(8) . 2_755
O9 C41 C43 123.9(12) . 2_665
C41 C41 C43 117.7(15) 2_755 2_665
C42 C41 C43 39.8(6) . 2_665
O9 C41 C43 92.9(7) 2_755 2_665
C43 C42 C41 94.3(9) 2_665 .
C42 C43 C41 45.9(6) 2_665 2_665
C41 O9 C41 49.4(10) . 2_755
C11 N1 C15 110.7(2) . .
C11 N1 C10 113.0(2) . .
C15 N1 C10 109.8(2) . .
C17 C16 C21 118.3(3) . .
C17 C16 C13 120.6(2) . .
C21 C16 C13 121.0(2) . .
C18 C17 C16 121.1(3) . .
C19 C18 C17 118.9(3) . .
O1 C7 C6 120.8(3) . .
O1 C7 C8 121.3(3) . .
C6 C7 C8 117.9(2) . .
O2 C13 C12 110.0(2) . .
O2 C13 C16 111.3(2) . .
C12 C13 C16 111.7(2) . .
O2 C13 C14 105.8(2) . .
C12 C13 C14 108.7(2) . .
C16 C13 C14 109.2(2) . .
C10 C9 C8 108.1(2) . .
C7 C8 C9 114.7(2) . .
C20 C21 C16 121.2(3) . .
C15 C14 C13 112.3(2) . .
C20 C19 C18 121.2(3) . .
C20 C19 Cl1 119.2(2) . .
C18 C19 Cl1 119.6(2) . .
C1 C6 C5 118.7(3) . .
C1 C6 C7 123.0(3) . .
C5 C6 C7 118.3(3) . .
N1 C15 C14 111.8(2) . .
N1 C11 C12 110.9(2) . .
N1 C10 C9 114.3(2) . .
C3 C4 C5 117.7(3) . .
C11 C12 C13 112.1(2) . .
C6 C1 C2 120.4(3) . .
C19 C20 C21 119.3(3) . .
F1 C3 C2 118.5(3) . .
F1 C3 C4 118.2(3) . .
C2 C3 C4 123.3(3) . .
C4 C5 C6 121.4(3) . .
C3 C2 C1 118.5(3) . .
C28 C23 C24 118.9(3) . .
C28 C23 C22 121.5(2) . .
C24 C23 C22 119.6(3) . .
C27 C28 C23 121.0(3) . .
O4 C22 O3 122.9(2) . .
O4 C22 C23 119.4(2) . .
O3 C22 C23 117.7(2) . .
C28 C27 C26 119.3(3) . .
O5 C26 C25 118.0(3) . .
O5 C26 C27 122.1(3) . .
C25 C26 C27 119.8(3) . .
C25 C24 C23 120.7(3) . .
C24 C25 C26 120.3(3) . .
O6 C29 O7 122.4(3) . .
O6 C29 C30 125.2(3) . .
O7 C29 C30 112.4(2) . .
C31 C30 C35 118.4(3) . .
C31 C30 C29 121.1(2) . .
C35 C30 C29 120.5(3) . .
C34 C35 C30 120.9(3) . .
C35 C34 C33 120.6(2) . .
C32 C31 C30 120.8(3) . .
C31 C32 C33 120.6(3) . .
O8 C33 C32 118.6(3) . .
O8 C33 C34 122.6(2) . .
C32 C33 C34 118.8(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C41 O9 0.943(9) .
C41 C41 1.320(15) 2_755
C41 C42 1.382(15) .
C41 O9 1.722(10) 2_755
C41 C43 1.920(17) 2_665
C42 C43 1.232(12) 2_665
C43 C42 1.232(12) 2_665
C43 C41 1.920(17) 2_665
O9 C41 1.722(10) 2_755
Cl1 C19 1.747(3) .
O2 C13 1.427(3) .
F1 C3 1.358(3) .
N1 C11 1.495(4) .
N1 C15 1.496(3) .
N1 C10 1.498(3) .
O1 C7 1.215(3) .
C16 C17 1.388(4) .
C16 C21 1.391(4) .
C16 C13 1.533(4) .
C17 C18 1.387(4) .
C18 C19 1.382(4) .
C7 C6 1.495(4) .
C7 C8 1.508(4) .
C13 C12 1.533(4) .
C13 C14 1.535(4) .
C9 C10 1.521(4) .
C9 C8 1.524(4) .
C21 C20 1.378(4) .
C14 C15 1.516(4) .
C19 C20 1.373(4) .
C6 C1 1.385(4) .
C6 C5 1.390(4) .
C11 C12 1.528(4) .
C4 C3 1.368(5) .
C4 C5 1.383(4) .
C1 C2 1.395(4) .
C3 C2 1.358(5) .
O4 C22 1.259(3) .
O3 C22 1.274(3) .
C23 C28 1.388(4) .
C23 C24 1.390(4) .
C23 C22 1.490(4) .
O5 C26 1.353(3) .
C28 C27 1.383(4) .
C27 C26 1.397(4) .
C26 C25 1.384(4) .
C24 C25 1.375(4) .
O8 C33 1.347(3) .
O6 C29 1.218(3) .
O7 C29 1.319(3) .
C29 C30 1.478(4) .
C30 C31 1.394(4) .
C30 C35 1.399(4) .
C35 C34 1.369(4) .
C34 C33 1.397(4) .
C31 C32 1.375(4) .
C32 C33 1.389(4) .
