#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:07:12 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179652 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/05/4510531.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_4510531
loop_
_publ_author_name
'Be̅rziņš, Agris'
'Skarbulis, Edgards'
'Rekis, Toms'
'Actiņš, Andris'
_publ_section_title
;
 On the Formation of Droperidol Solvates: Characterization of Structure
 and Properties
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2654
_journal_paper_doi               10.1021/cg5003447
_journal_volume                  14
_journal_year                    2014
_chemical_formula_moiety         '2(C22 H22 F N3 O2), C2 H6 O'
_chemical_formula_sum            'C46 H50 F2 N6 O5'
_chemical_formula_weight         804.92
_chemical_melting_point          399.0(10)
_chemical_name_common            'Droperidol ethanol solvate'
_chemical_name_systematic
; 
1-[1-[4-(4-Fluorophenyl)-4-oxobutyl]-1,2,3,6-tetrahydro-4-pyridyl]
-1,3-dihydro-2H-benzimidazol-2-one
;
_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                100.9299(10)
_cell_angle_beta                 92.6382(10)
_cell_angle_gamma                95.9415(15)
_cell_formula_units_Z            1
_cell_length_a                   6.08400(10)
_cell_length_b                   10.2978(3)
_cell_length_c                   16.1737(5)
_cell_measurement_temperature    173(2)
_cell_volume                     987.35(5)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0559
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7942
_diffrn_reflns_theta_full        29.11
_diffrn_reflns_theta_max         29.11
_diffrn_reflns_theta_min         2.60
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             426
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         5220
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0511
_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)+(0.0619P)²+0.2945P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1381
_reflns_number_gt                3784
_reflns_number_total             5220
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5003447_si_006.cif
_cod_data_source_block           SEt_droperidol_ethanol_solvate
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '398-400 K' was changed to
'399.0(10)' - the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4510531--4510537.cif.
;
_cod_original_cell_volume        987.35(4)
_cod_database_code               4510531
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
O1 O 1.00161(18) 0.67830(11) 0.05845(7) 0.0293(3) Uani 1 1 d .
C1 C 0.8383(2) 0.61701(15) 0.08178(10) 0.0240(3) Uani 1 1 d .
N2 N 0.7690(2) 0.48431(12) 0.05998(8) 0.0265(3) Uani 1 1 d .
H5 H 0.8356 0.4285 0.0252 0.032 Uiso 1 1 d R
C5 C 0.4467(3) 0.33427(16) 0.09562(11) 0.0322(4) Uani 1 1 d .
H4 H 0.4830 0.2549 0.0642 0.039 Uiso 1 1 calc R
C4 C 0.2594(3) 0.33794(17) 0.14189(11) 0.0346(4) Uani 1 1 d .
H3 H 0.1688 0.2593 0.1414 0.042 Uiso 1 1 calc R
C3 C 0.2045(3) 0.45655(17) 0.18879(11) 0.0325(4) Uani 1 1 d .
H2 H 0.0782 0.4555 0.2191 0.039 Uiso 1 1 calc R
C2 C 0.3347(3) 0.57663(16) 0.19129(10) 0.0270(3) Uani 1 1 d .
H1 H 0.2925 0.6618 0.2257 0.032 Uiso 1 1 d R
N1 N 0.6886(2) 0.67238(12) 0.13614(8) 0.0232(3) Uani 1 1 d .
C7 C 0.5764(3) 0.45346(15) 0.09845(10) 0.0250(3) Uani 1 1 d .
C6 C 0.5218(2) 0.57265(14) 0.14617(9) 0.0230(3) Uani 1 1 d .
C8 C 0.7035(2) 0.81080(14) 0.17440(9) 0.0221(3) Uani 1 1 d .
C9 C 0.5383(2) 0.88054(15) 0.16355(10) 0.0255(3) Uani 1 1 d .
H6 H 0.4156 0.8394 0.1283 0.031 Uiso 1 1 calc R
C10 C 0.5404(2) 1.02284(15) 0.20556(11) 0.0278(3) Uani 1 1 d .
H7 H 0.5625 1.0784 0.1638 0.033 Uiso 1 1 calc R
H8 H 0.3974 1.0357 0.2279 0.033 Uiso 1 1 calc R
N3 N 0.71363(19) 1.06577(12) 0.27422(8) 0.0223(3) Uani 1 1 d .
C11 C 0.9234(2) 1.02032(15) 0.24729(10) 0.0248(3) Uani 1 1 d .
H9 H 1.0396 1.0562 0.2912 0.030 Uiso 1 1 calc R
H10 H 0.9621 1.0533 0.1969 0.030 Uiso 1 1 calc R
C12 C 0.9084(2) 0.86922(15) 0.22900(10) 0.0256(3) Uani 1 1 d .
H11 H 1.0377 0.8412 0.2008 0.031 Uiso 1 1 calc R
H12 H 0.9058 0.8371 0.2816 0.031 Uiso 1 1 calc R
C13 C 0.7399(2) 1.21166(15) 0.30029(10) 0.0255(3) Uani 1 1 d .
H13 H 0.7650 1.2509 0.2511 0.031 Uiso 1 1 calc R
H14 H 0.8697 1.2388 0.3392 0.031 Uiso 1 1 calc R
C14 C 0.5404(2) 1.26519(15) 0.34221(10) 0.0260(3) Uani 1 1 d .
H15 H 0.5219 1.2322 0.3941 0.031 Uiso 1 1 calc R
H16 H 0.4083 1.2331 0.3051 0.031 Uiso 1 1 calc R
C15 C 0.5674(2) 1.41709(15) 0.36201(10) 0.0242(3) Uani 1 1 d .
H17 H 0.6999 1.4487 0.3990 0.029 Uiso 1 1 calc R
H18 H 0.5868 1.4497 0.3100 0.029 Uiso 1 1 calc R
C16 C 0.3714(2) 1.47303(15) 0.40357(10) 0.0252(3) Uani 1 1 d .
O2 O 0.2286(2) 1.40081(12) 0.42858(9) 0.0401(3) Uani 1 1 d .
C17 C 0.3501(2) 1.61851(15) 0.41344(9) 0.0230(3) Uani 1 1 d .
C18 C 0.1588(3) 1.66495(16) 0.44689(10) 0.0280(3) Uani 1 1 d .
H19 H 0.0525 1.6059 0.4641 0.034 Uiso 1 1 calc R
C19 C 0.1249(3) 1.79775(17) 0.45476(11) 0.0323(4) Uani 1 1 d .
H20 H -0.0015 1.8290 0.4777 0.039 Uiso 1 1 calc R
C20 C 0.2843(3) 1.88180(16) 0.42762(10) 0.0299(4) Uani 1 1 d .
C21 C 0.4768(3) 1.84172(16) 0.39568(11) 0.0310(4) Uani 1 1 d .
H21 H 0.5824 1.9018 0.3790 0.037 Uiso 1 1 calc R
C22 C 0.5090(3) 1.70870(15) 0.38900(10) 0.0275(3) Uani 1 1 d .
H22 H 0.6386 1.6793 0.3679 0.033 Uiso 1 1 calc R
F1 F 0.24911(19) 2.01123(10) 0.43278(7) 0.0440(3) Uani 1 1 d .
C23 C 0.1210(3) -0.0082(2) 0.00525(13) 0.0441(5) Uani 1 1 d .
H23A H 0.2078 0.0536 -0.0199 0.066 Uiso 1 1 d R
H23B H 0.1450 -0.0982 -0.0209 0.066 Uiso 0.50 1 d PR
H23C H 0.1667 0.0047 0.0647 0.066 Uiso 1 1 d R
O3 O 0.1694(4) -0.1256(2) -0.02931(17) 0.0408(6) Uani 0.50 1 d P
H24 H 0.1081 -0.1816 -0.0056 0.061 Uiso 0.50 1 calc PR
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'
F F 0.0171 0.0103 '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'
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
O1 C1 N2 127.66(14) . .
O1 C1 N1 125.65(14) . .
N2 C1 N1 106.69(13) . .
C1 N2 C7 110.50(13) . .
C1 N2 H5 123.7 . .
C7 N2 H5 125.8 . .
C7 C5 C4 117.12(15) . .
C7 C5 H4 121.4 . .
C4 C5 H4 121.4 . .
C3 C4 C5 121.53(16) . .
C3 C4 H3 119.2 . .
C5 C4 H3 119.2 . .
C2 C3 C4 121.28(16) . .
C2 C3 H2 119.4 . .
C4 C3 H2 119.4 . .
C6 C2 C3 117.13(15) . .
C6 C2 H1 122.6 . .
C3 C2 H1 120.3 . .
C1 N1 C6 109.38(12) . .
C1 N1 C8 124.36(13) . .
C6 N1 C8 126.26(12) . .
C5 C7 N2 131.64(15) . .
C5 C7 C6 121.29(15) . .
N2 C7 C6 107.07(13) . .
C2 C6 C7 121.63(14) . .
C2 C6 N1 132.04(14) . .
C7 C6 N1 106.34(13) . .
C9 C8 N1 120.44(13) . .
C9 C8 C12 122.35(13) . .
N1 C8 C12 117.16(12) . .
C8 C9 C10 122.59(13) . .
C8 C9 H6 118.7 . .
C10 C9 H6 118.7 . .
N3 C10 C9 113.04(12) . .
N3 C10 H7 109.0 . .
C9 C10 H7 109.0 . .
N3 C10 H8 109.0 . .
C9 C10 H8 109.0 . .
H7 C10 H8 107.8 . .
C11 N3 C10 110.15(11) . .
C11 N3 C13 109.95(11) . .
C10 N3 C13 110.33(11) . .
N3 C11 C12 111.18(12) . .
N3 C11 H9 109.4 . .
C12 C11 H9 109.4 . .
N3 C11 H10 109.4 . .
C12 C11 H10 109.4 . .
H9 C11 H10 108.0 . .
C8 C12 C11 110.32(12) . .
C8 C12 H11 109.6 . .
C11 C12 H11 109.6 . .
C8 C12 H12 109.6 . .
C11 C12 H12 109.6 . .
H11 C12 H12 108.1 . .
N3 C13 C14 113.21(12) . .
N3 C13 H13 108.9 . .
C14 C13 H13 108.9 . .
N3 C13 H14 108.9 . .
C14 C13 H14 108.9 . .
H13 C13 H14 107.7 . .
C13 C14 C15 111.39(13) . .
C13 C14 H15 109.4 . .
C15 C14 H15 109.4 . .
C13 C14 H16 109.4 . .
C15 C14 H16 109.4 . .
H15 C14 H16 108.0 . .
C16 C15 C14 112.53(13) . .
C16 C15 H17 109.1 . .
C14 C15 H17 109.1 . .
C16 C15 H18 109.1 . .
C14 C15 H18 109.1 . .
H17 C15 H18 107.8 . .
O2 C16 C17 119.43(14) . .
O2 C16 C15 120.75(14) . .
C17 C16 C15 119.82(13) . .
C22 C17 C18 118.72(14) . .
C22 C17 C16 123.16(13) . .
C18 C17 C16 118.10(14) . .
C19 C18 C17 121.00(15) . .
C19 C18 H19 119.5 . .
C17 C18 H19 119.5 . .
C20 C19 C18 117.88(15) . .
C20 C19 H20 121.1 . .
C18 C19 H20 121.1 . .
F1 C20 C21 118.41(16) . .
F1 C20 C19 118.20(15) . .
C21 C20 C19 123.40(15) . .
C20 C21 C22 117.93(16) . .
C20 C21 H21 121.0 . .
C22 C21 H21 121.0 . .
C21 C22 C17 121.03(15) . .
C21 C22 H22 119.5 . .
C17 C22 H22 119.5 . .
O3 C23 C23 113.7(2) . 2
O3 C23 H23A 106.3 . .
C23 C23 H23A 110.7 2 .
O3 C23 H23B 4.4 . .
C23 C23 H23B 109.4 2 .
H23A C23 H23B 109.4 . .
O3 C23 H23C 106.4 . .
C23 C23 H23C 109.8 2 .
H23A C23 H23C 109.7 . .
H23B C23 H23C 107.7 . .
C23 O3 H23B 12.8 . .
C23 O3 H24 109.5 . .
H23B O3 H24 101.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.2343(19) .
C1 N2 1.3615(19) .
C1 N1 1.3849(19) .
N2 C7 1.388(2) .
N2 H5 0.8700 .
C5 C7 1.381(2) .
C5 C4 1.392(3) .
C5 H4 0.9300 .
C4 C3 1.391(2) .
C4 H3 0.9300 .
C3 C2 1.391(2) .
C3 H2 0.9300 .
C2 C6 1.380(2) .
C2 H1 1.0096 .
N1 C6 1.4048(19) .
N1 C8 1.4341(18) .
C7 C6 1.400(2) .
C8 C9 1.318(2) .
C8 C12 1.496(2) .
C9 C10 1.492(2) .
C9 H6 0.9300 .
C10 N3 1.4660(18) .
C10 H7 0.9700 .
C10 H8 0.9700 .
N3 C11 1.4614(18) .
N3 C13 1.4711(18) .
C11 C12 1.520(2) .
C11 H9 0.9700 .
C11 H10 0.9700 .
C12 H11 0.9700 .
C12 H12 0.9700 .
C13 C14 1.520(2) .
C13 H13 0.9700 .
C13 H14 0.9700 .
C14 C15 1.526(2) .
C14 H15 0.9700 .
C14 H16 0.9700 .
C15 C16 1.508(2) .
C15 H17 0.9700 .
C15 H18 0.9700 .
C16 O2 1.2186(19) .
C16 C17 1.496(2) .
C17 C22 1.393(2) .
C17 C18 1.397(2) .
C18 C19 1.387(2) .
C18 H19 0.9300 .
C19 C20 1.376(3) .
C19 H20 0.9300 .
C20 F1 1.3595(18) .
C20 C21 1.372(2) .
C21 C22 1.388(2) .
C21 H21 0.9300 .
C22 H22 0.9300 .
C23 O3 1.301(3) .
C23 C23 1.504(4) 2
C23 H23A 0.9476 .
C23 H23B 0.9726 .
C23 H23C 0.9691 .
O3 H23B 0.3401 .
O3 H24 0.8200 .
