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_2020953
_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          'C21 H18 Cl N O3 S'
_chemical_formula_moiety         'C21 H18 Cl N O3 S'
_chemical_formula_sum            'C21 H18 Cl N O3 S'
_chemical_formula_weight         399.87
_chemical_name_systematic
;
<i>N</i>-[3-(2-Chlorobenzoyl)-5-ethylthiophen-2-yl]-2-methoxybenzamide
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                105.814(2)
_cell_angle_beta                 101.959(3)
_cell_angle_gamma                99.187(3)
_cell_formula_units_Z            2
_cell_length_a                   7.4798(3)
_cell_length_b                   11.4237(5)
_cell_length_c                   12.0933(5)
_cell_measurement_reflns_used    5014
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      29.196
_cell_measurement_theta_min      1.815
_cell_volume                     946.66(7)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEXII'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20919
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.550
_diffrn_reflns_theta_min         2.175
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.334
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_T_min  0.908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.299
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3959
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0451
_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^)+(0.0454P)^2^+0.2991P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1213
_reflns_number_gt                2406
_reflns_number_total             3959
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sk3680sup1.cif
_cod_data_source_block           V
_cod_database_code               2020953
_cod_database_fobs_code          2020953
_shelx_estimated_absorpt_t_min   0.921
_shelx_estimated_absorpt_t_max   0.952
_shelx_hkl_checksum              36242
_shelx_res_checksum              62263
_shelxl_version_number           2.014