# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_oxoabam _publ_contact_author ; Prof. Dr. Boese, Roland Institut f\"ur Anorganische Chemie der Universit\"at-GH Essen Universit\"atsstr. 3-5 D-45117 Essen, Germany ; _publ_contact_author_email 'boese@structchem.uni-essen.de' _publ_contact_author_phone '0049 201 183 2416' _publ_contact_author_fax '0049 201 183 2535' _publ_section_title ; An Alternate Synthesis of 2-(N-arylhydrazono)2,3- dihydrobenzothiophene-3-ones ; loop_ _publ_author_name _publ_author_address 'Zahra, Jalal A.' ; Chemistry Department Faculty of Science University of Jordan Amman, Jordan ; 'Abu Thaher, Bassam A.' ; Chemistry Department Faculty of Science Islamic University of Ghaza Ghaza Strip ; 'El-Abadelah, Mustafa M.' ; Chemistry Department Faculty of Science University of Jordan Amman, Jordan ; 'Boese, Roland' ; Institut f\"ur Anorganische Chemie der Universit\"at-GH Essen Universit\"atsstr. 3-5 D-45117 Essen, Germany ; _publ_requested_journal 'J. Org. Biomol. Chem.' _publ_requested_coeditor_name ? _publ_contact_letter ; ? ; _ccdc_compound_id '5b' _ccdc_biological_activity '?' _ccdc_polymorph '?' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-Oxo-2H-2-[N-(methylphenylhydrazono)]benzothiophene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H12 N2 O S' _chemical_formula_weight 268.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.949(5) _cell_length_b 8.165(3) _cell_length_c 12.755(5) _cell_angle_alpha 90.00 _cell_angle_beta 117.150(7) _cell_angle_gamma 90.00 _cell_volume 1292.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 1188 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 24.12 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.379 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.242 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.24 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ; Siemens SADABS program multi-scan V2.03 R.H. Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART CCD area detector system' _diffrn_measurement_method ; Fullsphere data collection in omega at 0.3 deg scan width, two runs with 720 frames, phi = 0, 270(deg) two runs with 436 frames, phi = 88, 180 deg) ; _diffrn_detector_area_resol_mean 512 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7070 _diffrn_reflns_av_R_equivalents 0.1643 _diffrn_reflns_av_sigmaI/netI 0.1290 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 24.00 _reflns_number_total 2012 _reflns_number_gt 1101 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART Vers. 5.054 1997/98' _computing_cell_refinement 'BRUKER AXS SAINT program Vers.6.01' _computing_data_reduction 'BRUKER AXS SAINT program Vers.6.01' _computing_structure_solution 'BRUKER AXS SHELXTL Vers.6.12,98/NT/2000/ME' _computing_structure_refinement 'BRUKER AXS SHELXTL Vers.6.12,98/NT/2000/ME' _computing_molecular_graphics 'BRUKER AXS SHELXTL Vers.6.12,98/NT/2000/ME' _computing_publication_material 'BRUKER AXS SHELXTL Vers.6.12,98/NT/2000/ME' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Comment: Please note that the esd’s of the cell Dimensions are probably too low; They should be multiplied by a factor of 2 to 10 ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0744P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ; Riding model on idealized geometrics with the 1.2 fold (1.5 fold for methyl groups) isotropic displacement parameters of the equivalent Uij of the corresponding carbon atom ; _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2012 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1283 _refine_ls_R_factor_gt 0.0669 _refine_ls_wR_factor_ref 0.1716 _refine_ls_wR_factor_gt 0.1423 _refine_ls_goodness_of_fit_ref 0.935 _refine_ls_restrained_S_all 0.935 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.40374(10) 0.82462(16) 0.01135(9) 0.0326(4) Uani 1 1 d . . . N1 N 0.5840(3) 0.6725(5) 0.0215(3) 0.0283(10) Uani 1 1 d . . . N2 N 0.6083(3) 0.6248(4) 0.1311(3) 0.0284(10) Uani 1 1 d . . . H2 H 0.5537 0.6641 0.1645 0.034 Uiso 1 1 d R . . O1 O 0.5233(3) 0.7841(4) -0.2096(3) 0.0376(9) Uani 1 1 d . . . C1 C 0.4975(3) 0.7594(5) -0.0359(4) 0.0260(11) Uani 1 1 d . . . C2 C 0.4698(4) 0.8151(6) -0.1583(4) 0.0273(11) Uani 1 1 d . . . C3 C 0.3206(4) 0.9898(6) -0.3125(4) 0.0331(13) Uani 1 1 d . . . H3 H 0.3497 0.9822 -0.3658 0.040 Uiso 1 1 d R . . C4 C 0.2285(4) 1.0773(6) -0.3403(4) 0.0378(13) Uani 1 1 d . . . H4 H 0.1942 1.1301 -0.4138 0.045 Uiso 1 1 d R . . C5 C 0.1854(4) 1.0899(6) -0.2619(4) 0.0401(14) Uani 1 1 d . . . H5 H 0.1217 1.1501 -0.2836 0.048 Uiso 1 1 d R . . C6 C 0.2343(4) 1.0144(6) -0.1526(4) 0.0372(13) Uani 1 1 d . . . H6 H 0.2054 1.0228 -0.0990 0.045 Uiso 1 1 d R . . C7 C 0.3272(4) 0.9268(5) -0.1254(4) 0.0271(12) Uani 1 1 d . . . C8 C 0.3713(4) 0.9107(6) -0.2020(4) 0.0279(12) Uani 1 1 d . . . C9 C 0.7039(4) 0.5359(6) 0.1964(4) 0.0283(12) Uani 1 1 d . . . C10 C 0.7230(4) 0.4824(6) 0.3073(4) 0.0363(13) Uani 1 1 d . . . H10 H 0.6738 0.5057 0.3368 0.044 Uiso 1 1 d R . . C11 C 0.8163(4) 0.3944(6) 0.3745(4) 0.0431(14) Uani 1 1 d . . . H11 H 0.8284 0.3562 0.4491 0.052 Uiso 1 1 d R . . C12 C 0.8916(4) 0.3614(6) 0.3357(4) 0.0366(13) Uani 1 1 d . . . C13 C 0.8696(4) 0.4148(6) 0.2239(4) 0.0458(15) Uani 1 1 d . . . H13 H 0.9184 0.3906 0.1942 0.055 Uiso 1 1 d R . . C14 C 0.7779(4) 0.5034(6) 0.1559(4) 0.0373(13) Uani 1 1 d . . . H14 H 0.7659 0.5419 0.0814 0.045 Uiso 1 1 d R . . C15 C 0.9926(4) 0.2643(7) 0.4104(5) 0.0548(17) Uani 1 1 d . . . H15A H 1.0281 0.2345 0.3631 0.082 Uiso 1 1 d R . . H15B H 0.9733 0.1659 0.4390 0.082 Uiso 1 1 d R . . H15C H 1.0410 0.3303 0.4768 0.082 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0388(7) 0.0404(9) 0.0151(6) 0.0032(6) 0.0093(5) 0.0039(7) N1 0.040(2) 0.029(2) 0.0099(19) 0.0008(17) 0.0059(17) -0.006(2) N2 0.033(2) 0.034(3) 0.014(2) 0.0023(17) 0.0073(17) 0.0007(19) O1 0.049(2) 0.047(2) 0.0162(17) 0.0038(15) 0.0142(16) 0.0073(18) C1 0.028(3) 0.025(3) 0.014(2) 0.002(2) 0.000(2) -0.005(2) C2 0.034(3) 0.028(3) 0.013(2) -0.005(2) 0.005(2) -0.008(2) C3 0.041(3) 0.033(3) 0.017(3) 0.000(2) 0.006(2) -0.002(3) C4 0.041(3) 0.032(3) 0.026(3) 0.004(2) 0.003(2) 0.007(3) C5 0.037(3) 0.037(4) 0.037(3) 0.002(2) 0.009(3) 0.001(3) C6 0.039(3) 0.041(4) 0.030(3) -0.003(2) 0.016(2) 0.001(3) C7 0.028(3) 0.023(3) 0.023(3) -0.002(2) 0.006(2) -0.004(2) C8 0.030(3) 0.033(3) 0.014(2) -0.006(2) 0.004(2) -0.005(2) C9 0.031(3) 0.031(3) 0.010(2) 0.000(2) -0.002(2) -0.001(2) C10 0.045(3) 0.038(3) 0.018(3) 0.004(2) 0.008(2) 0.000(3) C11 0.047(3) 0.050(4) 0.013(3) 0.008(2) -0.003(2) 0.000(3) C12 0.038(3) 0.027(3) 0.023(3) 0.002(2) -0.004(2) 0.001(3) C13 0.043(3) 0.051(4) 0.037(3) 0.000(3) 0.012(3) 0.004(3) C14 0.043(3) 0.041(4) 0.021(3) 0.008(2) 0.009(2) 0.008(3) C15 0.043(3) 0.051(4) 0.043(4) 0.005(3) -0.004(3) 0.008(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.755(5) . ? S1 C7 1.783(4) . ? N1 C1 1.299(5) . ? N1 N2 1.337(5) . ? N2 C9 1.410(6) . ? O1 C2 1.223(5) . ? C1 C2 1.497(6) . ? C2 C8 1.451(6) . ? C3 C4 1.368(6) . ? C3 C8 1.412(6) . ? C4 C5 1.386(7) . ? C5 C6 1.387(7) . ? C6 C7 1.379(6) . ? C7 C8 1.379(6) . ? C9 C14 1.374(6) . ? C9 C10 1.385(6) . ? C10 C11 1.388(7) . ? C11 C12 1.378(7) . ? C12 C13 1.384(6) . ? C12 C15 1.515(6) . ? C13 C14 1.379(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C7 90.8(2) . . ? C1 N1 N2 118.4(4) . . ? N1 N2 C9 119.2(4) . . ? N1 C1 C2 119.1(4) . . ? N1 C1 S1 128.1(3) . . ? C2 C1 S1 112.8(3) . . ? O1 C2 C8 127.4(4) . . ? O1 C2 C1 124.3(4) . . ? C8 C2 C1 108.2(4) . . ? C4 C3 C8 118.8(5) . . ? C3 C4 C5 121.1(5) . . ? C4 C5 C6 121.1(5) . . ? C7 C6 C5 117.2(5) . . ? C8 C7 C6 122.9(4) . . ? C8 C7 S1 112.8(3) . . ? C6 C7 S1 124.3(4) . . ? C7 C8 C3 118.7(4) . . ? C7 C8 C2 115.4(4) . . ? C3 C8 C2 125.8(4) . . ? C14 C9 C10 119.8(4) . . ? C14 C9 N2 123.2(4) . . ? C10 C9 N2 117.0(4) . . ? C9 C10 C11 118.9(5) . . ? C12 C11 C10 122.2(4) . . ? C11 C12 C13 117.5(4) . . ? C11 C12 C15 121.3(5) . . ? C13 C12 C15 121.2(5) . . ? C14 C13 C12 121.3(5) . . ? C9 C14 C13 120.3(5) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 24.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.482 _refine_diff_density_min -0.379 _refine_diff_density_rms 0.093