############################################################################## ### ### ### Electronic paper (Acta Crystallographica Section E) ### ### ### ############################################################################## # # # This CIF contains the data in a paper accepted for publication in Acta # # Crystallographica Section E. It conforms to the requirements of Notes # # for Authors for Section E, and has been peer reviewed under the auspices # # of the IUCr Commission on Journals. # # # # Full details of the Crystallographic Information File format # # are given in the paper "The Crystallographic Information File (CIF): # # a New Standard Archive File for Crystallography" by S. R. Hall, F. H. # # Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. # # # # The current version of the core CIF dictionary is obtainable from # # ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4. # # # # Software is freely available for graphical display of the structure(s) in # # this CIF. For information consult the CIF home page http://www.iucr.org/ # # cif/home.html # # # # This file may be used for bona fide research purposes within the # # scientific community so long as proper attribution is given to the journal # # article from which it was obtained. # # # ############################################################################## data_I _audit_creation_method 'WinGX routine CIF_UPDATE' _chemical_name_systematic ; 2-(2,2-Dibromoethenyl)thiophene ; _chemical_formula_moiety 'C6 H4 Br2 S' _chemical_formula_sum 'C6 H4 Br2 S' _chemical_formula_iupac 'C6 H4 Br2 S' _chemical_formula_weight 267.97 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 9.6843(19) _cell_length_b 7.2379(14) _cell_length_c 11.484(2) _cell_angle_alpha 90 _cell_angle_beta 109.16(3) _cell_angle_gamma 90 _cell_volume 760.4(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 980 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 26.99 _cell_measurement_temperature 173(2) _exptl_crystal_description plates _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 2.341 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 10.839 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details '(FACEIT in IPDS; Stoe & Cie, 1999)' _exptl_absorpt_correction_T_min 0.1878 _exptl_absorpt_correction_T_max 0.6584 _exptl_special_details ; ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe IPDS' _diffrn_measurement_method \f _diffrn_reflns_number 6492 _diffrn_reflns_av_R_equivalents 0.0637 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 26.99 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _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_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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^ > \s(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. ; _reflns_number_total 1667 _reflns_number_gt 1444 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0627 _refine_ls_R_factor_gt 0.0579 _refine_ls_wR_factor_ref 0.1388 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_number_reflns 1667 _refine_ls_number_parameters 82 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment noref _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1099P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.358 _refine_diff_density_min -1.732 _refine_ls_extinction_method none 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 0 '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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'EXPOSE in IPDS (Stoe & Cie, 1999)' _computing_cell_refinement 'CELL in IPDS (Stoe & Cie, 1999)' _computing_data_reduction 'INTEGRATE in IPDS (Stoe & Cie, 1999)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Br Br1 0.90429(5) 0.69525(7) 0.15399(5) 0.0306(2) Uani d . 1 . . Br Br2 0.75506(5) 0.94572(7) 0.30330(4) 0.0290(2) Uani d . 1 . . C C1 0.7287(5) 0.7946(6) 0.1647(4) 0.0214(9) Uani d . 1 . . C C2 0.5999(5) 0.7559(7) 0.0803(4) 0.0225(9) Uani d . 1 . . H H2 0.6061 0.6818 0.0139 0.027 Uiso calc R 1 . . C C3 0.4530(5) 0.8068(6) 0.0720(4) 0.0188(8) Uani d . 1 . . C C4 0.3277(5) 0.7471(7) -0.0213(4) 0.0225(9) Uani d . 1 . . H H4 0.3305 0.6695 -0.0873 0.027 Uiso calc R 1 . . C C5 0.1970(6) 0.8134(7) -0.0080(5) 0.0307(11) Uani d . 1 . . H H5 0.1026 0.7857 -0.0637 0.037 Uiso calc R 1 . . C C6 0.2213(5) 0.9216(7) 0.0939(5) 0.0289(10) Uani d . 1 . . H H6 0.1455 0.9771 0.1174 0.035 Uiso calc R 1 . . S S 0.40366(13) 0.94655(17) 0.17497(12) 0.0265(3) Uani d . 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br1 0.0220(3) 0.0379(4) 0.0324(3) 0.00528(18) 0.0097(2) -0.0004(2) Br2 0.0268(3) 0.0342(3) 0.0250(3) -0.00466(18) 0.0072(2) -0.00800(17) C1 0.024(2) 0.021(2) 0.0202(19) 0.0009(16) 0.0089(17) 0.0037(16) C2 0.024(2) 0.020(2) 0.024(2) 0.0027(18) 0.0104(18) 0.0016(17) C3 0.024(2) 0.0157(19) 0.0183(19) 0.0008(15) 0.0095(17) 0.0015(15) C4 0.024(2) 0.020(2) 0.024(2) 0.0029(17) 0.0083(18) 0.0041(17) C5 0.020(2) 0.034(3) 0.036(3) -0.0005(18) 0.005(2) 0.006(2) C6 0.022(2) 0.028(2) 0.037(3) -0.0003(18) 0.011(2) 0.003(2) S 0.0256(6) 0.0287(6) 0.0277(6) 0.0006(4) 0.0121(5) -0.0054(4) _geom_special_details ; All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Br1 C1 . 1.887(5) ? Br2 C1 . 1.878(5) ? C1 C2 . 1.335(7) ? C2 C3 . 1.442(6) ? C2 H2 . 0.95 ? C3 C4 . 1.397(7) ? C3 S . 1.738(4) ? C4 C5 . 1.408(7) ? C4 H4 . 0.95 ? C5 C6 . 1.362(8) ? C5 H5 . 0.95 ? C6 S . 1.714(5) ? C6 H6 . 0.95 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 C1 Br2 . . 124.9(4) ? C2 C1 Br1 . . 121.3(4) ? Br2 C1 Br1 . . 113.7(3) ? C1 C2 C3 . . 131.4(4) ? C1 C2 H2 . . 114.3 ? C3 C2 H2 . . 114.3 ? C4 C3 C2 . . 124.1(4) ? C4 C3 S . . 109.8(3) ? C2 C3 S . . 126.1(3) ? C3 C4 C5 . . 113.3(4) ? C3 C4 H4 . . 123.3 ? C5 C4 H4 . . 123.3 ? C6 C5 C4 . . 112.4(5) ? C6 C5 H5 . . 123.8 ? C4 C5 H5 . . 123.8 ? C5 C6 S . . 112.6(4) ? C5 C6 H6 . . 123.7 ? S C6 H6 . . 123.7 ? C6 S C3 . . 91.9(2) ? data_global _journal_date_recd_electronic 2010-12-06 _journal_date_accepted 2011-01-18 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2011 _journal_volume 67 _journal_issue 2 _journal_page_first o481 _journal_page_last o481 _journal_paper_category QO _journal_coeditor_code IM2256 _publ_contact_author_name 'Prof. Dr. Carsten Strohmann' _publ_contact_author_address ; Anorganische Chemie Technische Universit\"at Dortmund Otto-Hahn-Strasse 6 44227 Dortmund Germany ; _publ_contact_author_email mail@carsten-strohmann.de _publ_contact_author_fax 492317553797 _publ_contact_author_phone 492317553807 _publ_section_title ; 2-(2,2-Dibromoethenyl)thiophene ; loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Cl\'ement, Sebastien' . ; Institut UTINAM UMR CNRS 6213 Universit\'e de Franche-Comt\'e 16 Route de Gray La Bouloie 25030 Besan\,con France ; 'Guyard, Laurent' . ; Institut UTINAM UMR CNRS 6213 Universit\'e de Franche-Comt\'e 16 Route de Gray La Bouloie 25030 Besan\,con France ; 'Knorr, Michael' . ; Institut UTINAM UMR CNRS 6213 Universit\'e de Franche-Comt\'e 16 Route de Gray La Bouloie 25030 Besan\,con France ; 'Eckert, Prisca K.' . ; Anorganische Chemie Technische Universit\"at Dortmund Otto-Hahn-Strasse 6 44227 Dortmund Germany ; 'Strohmann, Carsten' . ; Anorganische Chemie Technische Universit\"at Dortmund Otto-Hahn-Strasse 6 44227 Dortmund Germany ;