Synthesis and structures of six closely related <i>N</i>-[3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl]arylamides, together with an isolated reaction intermediate: order <i>versus</i> disorder, molecular conformations and hydrogen bonding in zero, one and two dimensions
Sagar, Belakavadi K.; Yathirajan, Hemmige S.; Rathore, Ravindranath S.; Glidewell, Christopher; Acta Crystallographica Section C 74 (2018) –; doi:10.1107/S2053229618000657

data_2020954
_publ_section_title
;
 Synthesis and structures of six closely related
 <i>N</i>-[3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl]arylamides, together
 with an isolated reaction intermediate: order <i>versus</i> disorder,
 molecular conformations and hydrogen bonding in zero, one and two
 dimensions
;
_journal_coeditor_code           SK3680
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229618000657
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C20 H14 Cl F2 N O2 S'
_chemical_formula_moiety         'C20 H14 Cl F2 N O2 S'
_chemical_formula_sum            'C20 H14 Cl F2 N O2 S'
_chemical_formula_weight         405.83
_chemical_name_systematic
;
<i>N</i>-[3-(2-Chlorobenzoyl)-5-ethylthiophen-2-yl]-2,6-difluorobenzamide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 92.1050(10)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   58.0164(10)
_cell_length_b                   7.8002(2)
_cell_length_c                   16.1365(3)
_cell_measurement_reflns_used    6468
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      66.726
_cell_measurement_theta_min      3.049
_cell_volume                     7297.5(3)
_computing_cell_refinement
;
APEX2 (Bruker, 2012)
;
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS86 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa APEXII'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1086
_diffrn_reflns_limit_h_max       66
_diffrn_reflns_limit_h_min       -68
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            42600
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.726
_diffrn_reflns_theta_min         3.049
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.244
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_description       block
_exptl_crystal_F_000             3328
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.432
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     572
_refine_ls_number_reflns         6468
_refine_ls_number_restraints     70
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1190
_refine_ls_R_factor_gt           0.0659
_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^)+(0.0617P)^2^+13.9466P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1349
_refine_ls_wR_factor_ref         0.1587
_reflns_number_gt                3979
_reflns_number_total             6468
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sk3680sup1.cif
_cod_data_source_block           VI
_cod_database_code               2020954
_cod_database_fobs_code          2020954
_shelx_estimated_absorpt_t_min   0.642
_shelx_estimated_absorpt_t_max   0.737
_shelx_hkl_checksum              93595
_shelx_res_checksum              877
_shelxl_version_number           2.014