Structural Characterization and Rationalization of Formation, Stability, and Transformations of Benperidol Solvates
Be̅rziņš, Agris; Skarbulis, Edgars; Actiņš, Andris; Crystal Growth & Design 15 (2015) 2337–; doi:10.1021/acs.cgd.5b00138

data_4513138
_publ_section_title
;
 Structural Characterization and Rationalization of Formation, Stability,
 and Transformations of Benperidol Solvates
;
_journal_issue                   5
_journal_name_full               'Crystal Growth &amp; 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       '\f and \w 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/[\s^2^(Fo^2^)+(0.0782P)^2^+1.4376P]
 where P=(Fo^2^+2Fc^2^)/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 > 2\s(I)'
_cod_data_source_file            cg5b00138_si_009.cif
_cod_data_source_block           Benperidol_SEtOAc
_cod_database_code               4513138
_shelxl_version_number           2013-2
_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)
;
_shelx_res_checksum              83431
_shelx_hkl_checksum              58420
_olex2_submission_special_instructions 'No special instructions were received'