Synthesis, characterization, crystal structure and supramolecularity of ethyl (<i>E</i>)-2-cyano-3-(3-methylthiophen-2-yl)acrylate and a new polymorph of ethyl (<i>E</i>)-2-cyano-3-(thiophen-2-yl)acrylate
Al-Refai, Mahmoud; Ali, Basem F.; Said, Ala'a B.; Geyer, Armin; Marsch, Michael; Harms, Klaus; Acta Crystallographica Section E 75 (2019) 1357–1361; doi:10.1107/S2056989019011435

data_2243068
_publ_section_title
;
 Synthesis, characterization, crystal structure and supramolecularity of
 ethyl (<i>E</i>)-2-cyano-3-(3-methylthiophen-2-yl)acrylate and a new
 polymorph of ethyl (<i>E</i>)-2-cyano-3-(thiophen-2-yl)acrylate
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1357
_journal_page_last               1361
_journal_paper_doi               10.1107/S2056989019011435
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C10 H9 N O2 S'
_chemical_formula_moiety         'C10 H9 N O2 S'
_chemical_formula_sum            'C10 H9 N O2 S'
_chemical_formula_weight         207.24
_chemical_name_systematic
;
Ethyl (<i>E</i>)-2-cyano-3-(thiophen-2-yl)acrylate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 107.859(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5907(3)
_cell_length_b                   6.6883(2)
_cell_length_c                   13.4837(3)
_cell_measurement_reflns_used    15380
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.40
_cell_measurement_theta_min      3.45
_cell_volume                     994.92(5)
_computing_cell_refinement
;
<i>X-AREA Recipe</i> (Stoe & Cie, 2015)
;
_computing_data_collection
;
<i>X-AREA Pilatus</i> (Stoe & Cie, 2016)
;
_computing_data_reduction
;
<i>X-AREA Integrate</i> (Stoe & Cie, 2016) and <i>LANA</i> (Stoe & Cie,
2016)
;
_computing_molecular_graphics    'DIAMOND (Crystal Impact, 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 0.997
_diffrn_measured_fraction_theta_max 0.980
_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  0.0257
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10400
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         76.292
_diffrn_reflns_theta_min         6.836
_diffrn_source                   'GeniX 3D HF Cu'
_exptl_absorpt_coefficient_mu    2.676
_exptl_absorpt_correction_T_max  0.1679
_exptl_absorpt_correction_T_min  0.0505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>LANA</i>; Stoe & Cie, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.275
_refine_ls_extinction_coef       0.0030(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL-2018/3 (Sheldrick 2015)
;
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2048
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0334
_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^)+(0.0688P)^2^+0.2209P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1003
_reflns_number_gt                1974
_reflns_number_total             2048
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            tx2012sup1.cif
_cod_data_source_block           2
_cod_database_code               2243068
_cod_database_fobs_code          2243068
_shelx_estimated_absorpt_t_min   0.481
_shelx_estimated_absorpt_t_max   0.617
_shelx_hkl_checksum              85022
_shelx_res_checksum              3091