Crystal structures of 3,5-bis[(<i>E</i>)-3-hydroxybenzylidene]-1-methylpiperidin-4-one and 3,5-bis[(<i>E</i>)-2-chlorobenzylidene]-1-methylpiperidin-4-one
Eryanti, Yum; Zamri, Adel; Herlina, Tati; Supratman, Unang; Rosli, Mohd Mustaqim; Fun, Hoong-Kun; Acta Crystallographica Section E 71 (2015) 1488–1492; doi:10.1107/S2056989015020976

data_2241306
_publ_section_title
;
 Crystal structures of
 3,5-bis[(<i>E</i>)-3-hydroxybenzylidene]-1-methylpiperidin-4-one and
 3,5-bis[(<i>E</i>)-2-chlorobenzylidene]-1-methylpiperidin-4-one
;
_journal_coeditor_code           SU5232
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1488
_journal_page_last               1492
_journal_paper_doi               10.1107/S2056989015020976
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C20 H17 Cl2 N O'
_chemical_formula_moiety         'C20 H17 Cl2 N O'
_chemical_formula_sum            'C20 H17 Cl2 N O'
_chemical_formula_weight         358.24
_chemical_name_systematic
;
3,5-Bis[(<i>E</i>)-2-chlorobenzylidene]-1-methylpiperidin-4-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 98.671(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.540(3)
_cell_length_b                   10.623(4)
_cell_length_c                   21.119(7)
_cell_measurement_reflns_used    3908
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.23
_cell_measurement_theta_min      2.73
_cell_volume                     1672.2(11)
_computing_cell_refinement
;
SAINT (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2009)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009)
and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100.0(10)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX DUO CCD area-detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0839
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            3105
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.494
_diffrn_reflns_theta_min         1.951
_exptl_absorpt_coefficient_mu    0.394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>SADABS</i>; Bruker, 2009)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_description       needle
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.315
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.079
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.434
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3105
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.180
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0766
_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^)+13.4429P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1863
_refine_ls_wR_factor_ref         0.1918
_reflns_number_gt                2591
_reflns_number_total             3105
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            su5232sup1.cif
_cod_data_source_block           2
_cod_original_cell_volume        1672.2(10)
_cod_database_code               2241306
_cod_database_fobs_code          2241306
_shelx_estimated_absorpt_t_min   0.886
_shelx_estimated_absorpt_t_max   0.970
_shelx_hkl_checksum              56284
_shelx_res_checksum              6517