From small structural modifications to adjustment of structurally dependent properties: 1-methyl-3,5-bis[(<i>E</i>)-2-thienylidene]-4-piperidone and 3,5-bis[(<i>E</i>)-5-bromo-2-thienylidene]-1-methyl-4-piperidone
Tongwa, Paul; Kinnibrugh, Tiffany L.; Kicchaiahgari, Geetha R.; Khrustalev, Victor N.; Timofeeva, Tatiana V.; Acta Crystallographica Section C 65 (2009) o155–o159; doi:10.1107/S0108270109008336

data_2017055
_publ_section_title
;
 From small structural modifications to adjustment of structurally
 dependent properties:
 1-methyl-3,5-bis[(<i>E</i>)-2-thienylidene]-4-piperidone and
 3,5-bis[(<i>E</i>)-5-bromo-2-thienylidene]-1-methyl-4-piperidone
;
_journal_coeditor_code           GZ3158
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o155
_journal_page_last               o159
_journal_paper_doi               10.1107/S0108270109008336
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H13 Br2 N O S2'
_chemical_formula_moiety         'C16 H13 Br2 N O S2'
_chemical_formula_sum            'C16 H13 Br2 N O S2'
_chemical_formula_weight         459.21
_chemical_melting_point_gt       422
_chemical_melting_point_lt       423
_chemical_name_systematic
;
3,5-bis[(<i>E</i>)-5-bromo-2-thienylidene]-1-methyl-4-piperidone
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.222(3)
_cell_length_b                   5.8840(7)
_cell_length_c                   23.994(3)
_cell_measurement_reflns_used    6205
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.8181
_cell_measurement_theta_min      2.4411
_cell_volume                     3278.5(7)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w'
_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  0.0985
_diffrn_reflns_av_sigmaI/netI    0.0849
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            49136
_diffrn_reflns_theta_full        30.76
_diffrn_reflns_theta_max         30.76
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    5.199
_exptl_absorpt_correction_T_max  0.353
_exptl_absorpt_correction_T_min  0.111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.861
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.480
_refine_diff_density_min         -1.198
_refine_ls_abs_structure_details 'Flack (1983), with how many Friedel pairs?'
_refine_ls_abs_structure_Flack   0.347(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         10192
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0544
_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/[\s^2^(Fo^2^)+(0.0600P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1219
_reflns_number_gt                7285
_reflns_number_total             10192
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            gz3158.cif
_cod_data_source_block           II
_cod_original_cell_volume        3278.6(7)
_cod_database_code               2017055
_cod_database_fobs_code          2017055