#------------------------------------------------------------------------------
#$Date: 2015-06-04 06:27:43 +0300 (Thu, 04 Jun 2015) $
#$Revision: 137838 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/31/4513138.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_4513138
loop_
_publ_author_name
'Be̅rziņš, Agris'
'Skarbulis, Edgars'
'Actiņš, Andris'
_publ_section_title
;
 Structural Characterization and Rationalization of Formation, Stability,
 and Transformations of Benperidol Solvates
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2337
_journal_paper_doi               10.1021/acs.cgd.5b00138
_journal_volume                  15
_journal_year                    2015
_chemical_formula_moiety         'C22 H24 F N3 O2, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C24 H28 F N3 O3'
_chemical_formula_weight         425.49
_chemical_name_common            'benperidol ethyl acetate solvate'
_chemical_name_systematic
;
1-{1-[4-(4-fluorophenyl)-4-oxobutyl]piperidin-4-yl}
-1,3-dihydro-2H-benzimidazol-2-one ethyl acetate solvate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-12-30
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_cell_angle_alpha                109.936(3)
_cell_angle_beta                 90.199(2)
_cell_angle_gamma                100.322(3)
_cell_formula_units_Z            2
_cell_length_a                   5.4228(3)
_cell_length_b                   14.6014(8)
_cell_length_c                   14.8045(10)
_cell_measurement_temperature    100(2)
_cell_volume                     1081.50(11)
_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_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.933
_diffrn_measured_fraction_theta_max 0.969
_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  0.0635
_diffrn_reflns_av_unetI/netI     0.0919
_diffrn_reflns_laue_measured_fraction_full 0.933
_diffrn_reflns_laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5857
_diffrn_reflns_point_group_measured_fraction_full 0.933
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         24.895
_diffrn_reflns_theta_min         2.795
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3659
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1130
_refine_ls_R_factor_gt           0.0751
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0782P)²+1.4376P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1734
_refine_ls_wR_factor_ref         0.1992
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2532
_reflns_number_total             3659
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg5b00138_si_009.cif
_cod_data_source_block           Benperidol_SEtOAc
_cod_database_code               4513138
_shelxl_version_number           2013-2
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: O29(0.5) C30(0.5) O31(0.5) C37(0.5) H37A(0.5) H37B(0.5) H37C(0.5)
 C29A(0.5) H29B(0.5) H29A(0.5) C30A(0.5) H30A(0.5) H30B(0.5) H30C(0.5)
3.a Riding coordinates:
 O29(C30,O31,C37,H37A,H37B,H37C,C29A,H29B,H29A,C30A,H30A,H30B,H30C)
3.b Ternary CH refined with riding coordinates:
 C8(H8)
3.c Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C9(H9A,H9B), C13(H13A,H13B), C12(H12A,H12B), C15(H15A,H15B),
 C14(H14A,H14B), C11(H11A,H11B)
3.d Aromatic/amide H refined with riding coordinates:
 C22(H22), C19(H19), C2(H2A), C21(H21), C18(H18), C4(H4), C5(H5), C3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_occupancy
O1 O 0.4540(4) 0.92222(17) 0.08013(17) 0.0277(6) Uani 1 1 d . .
F1 F -0.6525(4) 0.45931(17) 0.83440(16) 0.0422(6) Uani 1 1 d . .
O2 O -0.7162(4) 0.62036(18) 0.49416(18) 0.0309(6) Uani 1 1 d . .
N3 N -0.0275(5) 0.8554(2) 0.3950(2) 0.0256(7) Uani 1 1 d . .
C22 C -0.3693(6) 0.6093(3) 0.6991(3) 0.0283(8) Uani 1 1 d . .
H22 H -0.2188 0.6514 0.6989 0.034 Uiso 1 1 calc R .
C16 C -0.5377(6) 0.6360(2) 0.5519(2) 0.0230(7) Uani 1 1 d . .
N1 N 0.1599(5) 0.9893(2) 0.1832(2) 0.0249(6) Uani 1 1 d . .
C19 C -0.8210(6) 0.4848(3) 0.7004(3) 0.0303(8) Uani 1 1 d . .
H19 H -0.9712 0.4432 0.7019 0.036 Uiso 1 1 calc R .
N2 N 0.2718(5) 1.0521(2) 0.0703(2) 0.0242(7) Uani 1 1 d . .
H2 H 0.354(8) 1.066(3) 0.026(3) 0.049(13) Uiso 1 1 d . .
C10 C -0.0950(6) 0.7944(3) 0.2943(2) 0.0287(8) Uani 1 1 d . .
H10A H -0.2590 0.7527 0.2889 0.034 Uiso 1 1 calc R .
H10B H 0.0258 0.7515 0.2715 0.034 Uiso 1 1 calc R .
C17 C -0.5633(6) 0.5911(2) 0.6287(2) 0.0224(7) Uani 1 1 d . .
C9 C -0.1009(6) 0.8577(3) 0.2314(3) 0.0290(8) Uani 1 1 d . .
H9A H -0.2316 0.8966 0.2504 0.035 Uiso 1 1 calc R .
H9B H -0.1391 0.8151 0.1646 0.035 Uiso 1 1 calc R .
C8 C 0.1528(6) 0.9267(3) 0.2420(2) 0.0252(8) Uani 1 1 d . .
H8 H 0.2766 0.8842 0.2182 0.030 Uiso 1 1 calc R .
C13 C -0.0335(6) 0.7942(3) 0.4556(3) 0.0270(8) Uani 1 1 d . .
H13A H 0.0480 0.8353 0.5184 0.032 Uiso 1 1 calc R .
H13B H 0.0628 0.7427 0.4272 0.032 Uiso 1 1 calc R .
C12 C 0.2294(6) 0.9852(3) 0.3471(3) 0.0280(8) Uani 1 1 d . .
H12A H 0.3980 1.0237 0.3531 0.034 Uiso 1 1 calc R .
H12B H 0.1166 1.0311 0.3726 0.034 Uiso 1 1 calc R .
C7 C 0.0980(6) 1.1048(2) 0.1215(2) 0.0243(7) Uani 1 1 d . .
C15 C -0.2912(6) 0.6990(3) 0.5459(2) 0.0251(8) Uani 1 1 d . .
H15A H -0.1633 0.6584 0.5329 0.030 Uiso 1 1 calc R .
H15B H -0.2439 0.7513 0.6079 0.030 Uiso 1 1 calc R .
C2 C -0.1540(6) 1.1008(3) 0.2550(3) 0.0275(8) Uani 1 1 d . .
H2A H -0.2038 1.0749 0.3029 0.033 Uiso 1 1 calc R .
C6 C 0.0252(6) 1.0653(2) 0.1928(2) 0.0236(7) Uani 1 1 d . .
C21 C -0.3987(6) 0.5656(3) 0.7685(3) 0.0320(8) Uani 1 1 d . .
H21 H -0.2698 0.5774 0.8150 0.038 Uiso 1 1 calc R .
C20 C -0.6236(6) 0.5042(3) 0.7671(3) 0.0299(8) Uani 1 1 d . .
C14 C -0.2961(6) 0.7456(3) 0.4690(3) 0.0277(8) Uani 1 1 d . .
H14A H -0.4021 0.7951 0.4872 0.033 Uiso 1 1 calc R .
H14B H -0.3675 0.6950 0.4086 0.033 Uiso 1 1 calc R .
C1 C 0.3087(6) 0.9821(3) 0.1076(2) 0.0252(8) Uani 1 1 d . .
C11 C 0.2222(6) 0.9174(3) 0.4050(3) 0.0283(8) Uani 1 1 d . .
H11A H 0.3453 0.8753 0.3831 0.034 Uiso 1 1 calc R .
H11B H 0.2661 0.9570 0.4724 0.034 Uiso 1 1 calc R .
C18 C -0.7901(6) 0.5288(3) 0.6315(3) 0.0266(8) Uani 1 1 d . .
H18 H -0.9216 0.5170 0.5860 0.032 Uiso 1 1 calc R .
C4 C -0.1839(6) 1.2161(3) 0.1716(3) 0.0299(8) Uani 1 1 d . .
H4 H -0.2566 1.2668 0.1653 0.036 Uiso 1 1 calc R .
C5 C -0.0030(6) 1.1803(3) 0.1096(3) 0.0276(8) Uani 1 1 d . .
H5 H 0.0476 1.2064 0.0620 0.033 Uiso 1 1 calc R .
C3 C -0.2562(6) 1.1772(3) 0.2424(3) 0.0291(8) Uani 1 1 d . .
H3 H -0.3770 1.2026 0.2829 0.035 Uiso 1 1 calc R .
O4 O 0.0716(5) 0.5085(2) 0.0122(3) 0.0444(16) Uani 0.5 1 d . P
C24 C 0.1170(5) 0.6002(2) 0.0115(3) 0.0399(19) Uiso 0.5 1 d R P
O3 O -0.0241(5) 0.6327(2) -0.0250(3) 0.0592(18) Uani 0.5 1 d R P
C23 C 0.3668(5) 0.6586(2) 0.0622(3) 0.047(2) Uiso 0.5 1 d R P
H23A H 0.4658 0.6152 0.0903 0.070 Uiso 0.5 1 d R P
H23B H 0.3356 0.7237 0.1202 0.070 Uiso 0.5 1 d R P
H23C H 0.4793 0.6839 0.0119 0.070 Uiso 0.5 1 d R P
C25 C -0.1593(5) 0.4457(2) -0.0335(3) 0.045(3) Uiso 0.5 1 d R P
H25B H -0.1694 0.4397 -0.1084 0.054 Uiso 0.5 1 d R P
H25A H -0.3131 0.4796 0.0001 0.054 Uiso 0.5 1 d R P
C26 C -0.1657(5) 0.3460(2) -0.0228(3) 0.061(3) Uiso 0.5 1 d R P
H26A H -0.1550 0.3530 0.0524 0.091 Uiso 0.5 1 d R P
H26B H -0.3397 0.2959 -0.0570 0.091 Uiso 0.5 1 d R P
H26C H -0.0105 0.3130 -0.0566 0.091 Uiso 0.5 1 d R P
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
C10 N3 C13 111.3(3) . .
C10 N3 C11 110.1(3) . .
C13 N3 C11 110.0(3) . .
C21 C22 C17 120.8(3) . .
O2 C16 C17 119.8(3) . .
O2 C16 C15 121.0(3) . .
C17 C16 C15 119.2(3) . .
C6 N1 C8 127.9(3) . .
C1 N1 C8 123.4(3) . .
C1 N1 C6 108.7(3) . .
C18 C19 C20 118.2(3) . .
C1 N2 C7 109.7(3) . .
N3 C10 C9 111.7(3) . .
C22 C17 C16 122.4(3) . .
C22 C17 C18 118.6(3) . .
C18 C17 C16 119.0(3) . .
C10 C9 C8 110.0(3) . .
N1 C8 C9 112.8(3) . .
N1 C8 C12 113.0(3) . .
C12 C8 C9 110.4(3) . .
N3 C13 C14 114.1(3) . .
C11 C12 C8 111.2(3) . .
N2 C7 C6 106.9(3) . .
C5 C7 N2 131.1(3) . .
C5 C7 C6 121.9(3) . .
C16 C15 C14 113.8(3) . .
C6 C2 C3 116.8(3) . .
C7 C6 N1 106.8(3) . .
C2 C6 N1 132.2(3) . .
C2 C6 C7 121.0(3) . .
C20 C21 C22 118.2(3) . .
F1 C20 C19 118.2(3) . .
F1 C20 C21 118.5(3) . .
C21 C20 C19 123.2(3) . .
C15 C14 C13 111.1(3) . .
O1 C1 N1 125.0(3) . .
O1 C1 N2 127.2(3) . .
N2 C1 N1 107.8(3) . .
N3 C11 C12 111.1(3) . .
C19 C18 C17 121.0(3) . .
C3 C4 C5 120.7(3) . .
C7 C5 C4 117.4(3) . .
C4 C3 C2 122.1(3) . .
O4 O4 C24 98.4(4) 2_565 .
O4 O4 C24 52.4(3) 2_565 2_565
O4 O4 C25 20.2(4) 2_565 .
C24 O4 C24 150.8(2) . 2_565
C24 O4 C25 118.0 . .
C25 O4 O4 136.6(9) 2_565 2_565
C25 O4 C24 33.1(2) . 2_565
C25 O4 C24 166.1(8) 2_565 2_565
C25 O4 C24 40.1(5) 2_565 .
C25 O4 C25 156.9(5) 2_565 .
O4 C24 O4 29.2(2) . 2_565
O4 C24 C23 112.6 . .
O3 C24 O4 123.5 . .
O3 C24 O4 94.4(2) . 2_565
O3 C24 C23 123.9 . .
C23 C24 O4 141.6(2) . 2_565
C25 C24 O4 30.9(4) 2_565 .
C25 C24 O4 59.5(3) 2_565 2_565
C25 C24 O3 153.5(3) 2_565 .
C25 C24 C23 82.2(3) 2_565 .
C26 C24 O4 163.0(7) 2_565 2_565
C26 C24 O4 164.2(5) 2_565 .
C26 C24 O3 71.2(4) 2_565 .
C26 C24 C23 53.1(4) 2_565 .
C26 C24 C25 133.7(8) 2_565 2_565
C26 O3 C24 36.6(3) 2_565 .
C24 C23 C25 32.8(2) . 2_565
C26 C23 C24 29.2(3) 2_565 .
C26 C23 C25 61.7(2) 2_565 2_565
O4 C25 O4 23.1(5) 2_565 .
O4 C25 C24 109.0(7) 2_565 2_565
O4 C25 C23 169.6(8) 2_565 2_565
O4 C25 C23 152.4(2) . 2_565
O4 C25 C26 107.7 . .
O4 C25 C26 129.7(5) 2_565 .
C24 C25 O4 87.5(3) 2_565 .
C24 C25 C23 65.0(3) 2_565 2_565
C24 C25 C26 20.8(4) 2_565 .
C26 C25 C23 45.0(2) . 2_565
C24 C26 O3 72.2(4) 2_565 2_565
C24 C26 C23 97.7(6) 2_565 2_565
C24 C26 C25 25.5(5) 2_565 .
O3 C26 C23 168.0(6) 2_565 2_565
O3 C26 C25 97.3(3) 2_565 .
C23 C26 C25 73.4(3) 2_565 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.247(4) .
F1 C20 1.362(4) .
O2 C16 1.226(4) .
N3 C10 1.457(4) .
N3 C13 1.463(4) .
N3 C11 1.464(4) .
C22 C17 1.402(5) .
C22 C21 1.378(5) .
C16 C17 1.489(5) .
C16 C15 1.503(4) .
N1 C8 1.458(4) .
N1 C6 1.404(4) .
N1 C1 1.368(4) .
C19 C20 1.377(5) .
C19 C18 1.375(5) .
N2 C7 1.386(4) .
N2 C1 1.359(4) .
C10 C9 1.522(5) .
C17 C18 1.402(5) .
C9 C8 1.525(5) .
C8 C12 1.512(5) .
C13 C14 1.519(5) .
C12 C11 1.511(5) .
C7 C6 1.393(5) .
C7 C5 1.376(5) .
C15 C14 1.515(5) .
C2 C6 1.386(5) .
C2 C3 1.396(5) .
C21 C20 1.374(5) .
C4 C5 1.394(5) .
C4 C3 1.379(5) .
O4 O4 0.814(5) 2_565
O4 C24 1.651(5) 2_565
O4 C24 1.3214 .
O4 C25 0.717(6) 2_565
O4 C25 1.4233 .
C24 O4 1.651(5) 2_565
C24 O3 1.1853 .
C24 C23 1.5055 .
C24 C25 0.901(6) 2_565
C24 C26 0.742(6) 2_565
O3 C26 1.179(6) 2_565
C23 C25 1.646(5) 2_565
C23 C26 1.214(6) 2_565
C25 O4 0.717(6) 2_565
C25 C24 0.901(6) 2_565
C25 C23 1.646(5) 2_565
C25 C26 1.5118 .
C26 C24 0.742(6) 2_565
C26 O3 1.179(6) 2_565
C26 C23 1.214(6) 2_565
