Unexpected formation of a co-crystal containing the chalcone (<i>E</i>)-1-(5-chlorothiophen-2-yl)-3-(3-methylthiophen-2-yl)prop-2-en-1-one and the keto‒enol tautomer (<i>Z</i>)-1-(5-chlorothiophen-2-yl)-3-(3-methylthiophen-2-yl)prop-1-en-1-ol
Al-Refai, Mahmoud; Ali, Basem F.; Geyer, Armin; Harms, Klaus; Marsch, Michael; Acta Crystallographica Section E 76 (2020) 477–480; doi:10.1107/S2056989020002583

data_2243304
_publ_section_title
;
 Unexpected formation of a co-crystal containing the chalcone
 (<i>E</i>)-1-(5-chlorothiophen-2-yl)-3-(3-methylthiophen-2-yl)prop-2-en-1-one
 and the keto--enol tautomer
 (<i>Z</i>)-1-(5-chlorothiophen-2-yl)-3-(3-methylthiophen-2-yl)prop-1-en-1-ol
;
_journal_coeditor_code           HB7894
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              477
_journal_page_last               480
_journal_paper_doi               10.1107/S2056989020002583
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          '0.93C12 H9 Cl O S2, 0.07C12 H11 Cl O S2'
_chemical_formula_moiety         '0.93(C12 H9 Cl O S2), 0.07(C12 H11 Cl O S2)'
_chemical_formula_sum            'C12 H9.14 Cl O S2'
_chemical_formula_weight         268.90
_chemical_name_systematic
;
(<i>E</i>)-1-(5-Chlorothiophen-2-yl)-3-(3-methylthiophen-2-yl)prop-2-en-1-\
one--(<i>Z</i>)-1-(5-chlorothiophen-2-yl)-3-(3-methylthiophen-2-yl)prop-\
1-en-1-ol (0.93/0/07)
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                84.126(4)
_cell_angle_beta                 76.694(4)
_cell_angle_gamma                62.372(4)
_cell_formula_units_Z            2
_cell_length_a                   7.3709(4)
_cell_length_b                   7.5063(4)
_cell_length_c                   12.4247(6)
_cell_measurement_reflns_used    17498
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.95
_cell_measurement_theta_min      3.66
_cell_volume                     592.69(6)
_computing_cell_refinement
;
X-Area (Stoe & Cie, 2016)
;
_computing_data_collection
;
X-Area (Stoe & Cie, 2016)
;
_computing_data_reduction
;
X-Area (Stoe & Cie, 2016)
;
_computing_molecular_graphics
;
DIAMOND (Putz & Brandenburg, 2014)
;
_computing_publication_material
;
X-Area (Stoe & Cie, 2016)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.81
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Stoe Stadivari'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10865
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         75.476
_diffrn_reflns_theta_min         6.657
_diffrn_source                   'GeniX 3D HF Cu'
_exptl_absorpt_coefficient_mu    5.928
_exptl_absorpt_correction_T_max  0.3517
_exptl_absorpt_correction_T_min  0.0785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>LANA</i>; Stoe, 2016)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.279
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         2398
_refine_ls_number_restraints     754
_refine_ls_restrained_S_all      0.943
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0323
_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^)+(0.0480P)^2^+0.4005P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0884
_reflns_number_gt                2221
_reflns_number_total             2398
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb7894sup1.cif
_cod_data_source_block           I
_cod_database_code               2243304
_shelx_estimated_absorpt_t_min   0.319
_shelx_estimated_absorpt_t_max   0.491
_shelx_hkl_checksum              29389
_shelx_res_checksum              33995
_cod_database_fobs_code 2243304