Crystal structure and Hirshfeld surface analysis of ethyl 2-({5-acetyl-3-cyano-6-methyl-4-[(<i>E</i>)-2-phenylethenyl]pyridin-2-yl}sulfanyl)acetate
Al-Waleedy, Safiyyah A. H.; Mohamed, Shaaban K.; Mague, Joel T.; Akkurt, Mehmet; Abbady, Mohamed S.; Bakhite, Etify A.; Acta Crystallographica Section E 77 (2021) 730–733; doi:10.1107/S2056989021005600

data_2243857
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of ethyl
 2-({5-acetyl-3-cyano-6-methyl-4-[(<i>E</i>)-2-phenylethenyl]pyridin-2-yl}sulfanyl)acetate
;
_journal_coeditor_code           WM5610
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              730
_journal_page_last               733
_journal_paper_doi               10.1107/S2056989021005600
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C21 H20 N2 O3 S'
_chemical_formula_moiety         'C21 H20 N2 O3 S'
_chemical_formula_sum            'C21 H20 N2 O3 S'
_chemical_formula_weight         380.45
_chemical_name_systematic
'Ethyl 2-({5-acetyl-3-cyano-6-methyl-4-[(<i>E</i>)-2-phenylethenyl]pyridin-2-yl}sulfanyl)acetate'
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90.0660(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7365(4)
_cell_length_b                   9.7590(3)
_cell_length_c                   18.5600(7)
_cell_measurement_reflns_used    9951
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      74.6235
_cell_measurement_theta_min      4.7559
_cell_volume                     1944.67(12)
_computing_cell_refinement
;
<i>SAINT</i> (Bruker, 2016)
;
_computing_data_collection
;
<i>APEX3</i> (Bruker, 2016)
;
_computing_data_reduction
;
<i>SAINT</i>  (Bruker, 2016)
;
_computing_molecular_graphics
;
<i>DIAMOND</i> (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
<i>SHELXL</i> (Sheldrick, 2015<i>b</i>)
;
_computing_structure_solution
;
<i>SHELXT</i> (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14722
_diffrn_reflns_theta_full        70.000
_diffrn_reflns_theta_max         74.623
_diffrn_reflns_theta_min         4.756
_diffrn_source                   'INCOATEC I\mS micro--focus source'
_exptl_absorpt_coefficient_mu    1.672
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>SADABS</i>; Krause <i>et al.</i>, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.268
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.285
_refine_ls_extinction_coef       0.0041(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
<i>SHELXL 2018/3</i> (Sheldrick, 2015<i>b</i>)
;
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         3912
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0334
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0426P)^2^+0.7692P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0882
_reflns_number_gt                3520
_reflns_number_total             3912
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            wm5610sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2243857
_shelx_estimated_absorpt_t_min   0.663
_shelx_estimated_absorpt_t_max   0.918
_shelx_hkl_checksum              67839
_shelx_res_checksum              41469
_cod_database_fobs_code 2243857