data_8939sadabs _publ_requested_journal 'test 8939' _publ_section_title ; ? Title ; loop_ _publ_author_name _publ_author_address 'Javier Pena Gonzalez' ; Max-Planck-Institut f\"ur Kohlenforschung Kaiser-Wilhelm-Platz 1 45470 M\"ulheim an der Ruhr Germany ; 'Manuel Alcarazo' ; Max-Planck-Institut f\"ur Kohlenforschung Kaiser-Wilhelm-Platz 1 45470 M\"ulheim an der Ruhr Germany ; 'Elke Dreher' ; Max-Planck-Institut f\"ur Kohlenforschung Kaiser-Wilhelm-Platz 1 45470 M\"ulheim an der Ruhr Germany ; 'Christian W. Lehmann' ; Max-Planck-Institut f\"ur Kohlenforschung Kaiser-Wilhelm-Platz 1 45470 M\"ulheim an der Ruhr Germany ; _audit_block_code PEJ-PA-015-01 _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M 'c 2/c' _symmetry_space_group_name_Hall '-c 2yc' _symmetry_Int_Tables_number 15 _audit_creation_date 2014-08-14 _audit_creation_method ; Olex2 1.2 (compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862) ; _shelxl_version_number 2014/6 _publ_contact_author_address ? _publ_contact_author_email ? _publ_contact_author_phone ? _publ_section_references ; Bourhis, L.J., Dolomanov, O.V., Gildea, R.J., Howard, J.A.K., Puschmann, H. (2013). in preparation. Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; _chemical_name_systematic ; Title ; _chemical_compound_source dichloromethane _chemical_formula_moiety 'C11 H20 Br2 N2 S' _chemical_formula_sum 'C11 H20 Br2 N2 S' _chemical_formula_weight 372.17 _chemical_melting_point ? 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' 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' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 10.9428(7) _cell_length_b 12.0932(9) _cell_length_c 11.9149(13) _cell_angle_alpha 90 _cell_angle_beta 110.582(8) _cell_angle_gamma 90 _cell_volume 1476.1(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 16712 _cell_measurement_temperature 100 _cell_measurement_theta_max 33.0997 _cell_measurement_theta_min 2.6044 _shelx_estimated_absorpt_T_max ? _shelx_estimated_absorpt_T_min ? _exptl_absorpt_coefficient_mu 5.612 _exptl_absorpt_correction_T_max 0.84518 _exptl_absorpt_correction_T_min 0.70105 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details 'SADABS (Bruker AXS, 2012)' _exptl_absorpt_special_details ? _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.675 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 -1.00 2.00 0.0200 0.00 1.00 -2.00 0.0200 1.00 0.00 0.00 0.0200 -1.00 0.00 0.00 0.0200 0.00 1.00 0.00 0.0300 0.00 -1.00 0.00 0.0300 _exptl_crystal_description prism _exptl_crystal_F_000 744 _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0460 _diffrn_reflns_av_unetI/netI 0.0290 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 15473 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 27.500 _diffrn_reflns_theta_max 33.125 _diffrn_reflns_theta_min 2.606 _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean 18.02 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker AXS Enraf-Nonius KappaCCD' _diffrn_measurement_method 'CCD \f- and \w-scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source '0.2 x 2mm^2^ focus rotating anode' _diffrn_standards_number 0 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 2411 _reflns_number_total 2818 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement 'REVALCCD V. 1.6, 2008' _computing_data_collection 'DATCOL (Bruker AXS, 2006)' _computing_data_reduction 'REVALCCD V. 1.6, 2008' _computing_molecular_graphics 'DIAMOND (Crystal Impact GbR, 1997-2013)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL (Sheldrick, 2013)' _computing_structure_solution 'SHELXS (Sheldrick, 2013)' _refine_diff_density_max 0.633 _refine_diff_density_min -0.927 _refine_diff_density_rms 0.100 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 77 _refine_ls_number_reflns 2818 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0367 _refine_ls_R_factor_gt 0.0286 _refine_ls_restrained_S_all 1.068 _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^)+(0.0358P)^2^+1.1830P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0690 _refine_ls_wR_factor_ref 0.0731 _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. The minimum and maximum estimated transmissions from the multi-scan scaling are 0.6526 and 0.8954 (SADABS). There is a large Hirshfeld test difference for the atoms S1 and Br1. This is probably due to slight rotation of the Br-S-Br unit relative to the rest of the molecule about the C1-S1 bond. Highest peak ? Deepest hole ? ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C4(H4) 2.b Idealised Me refined as rotating group: C3(H3A,H3B,H3C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.00349(2) 0.27889(2) 0.04094(2) 0.02398(6) Uani 1 1 d . . . . . S1 S 0.0000 0.27447(4) 0.2500 0.01869(10) Uani 1 2 d S T P . . N1 N 0.10544(12) 0.48334(10) 0.29938(11) 0.0166(2) Uani 1 1 d . . . . . C1 C 0.0000 0.41805(17) 0.2500 0.0165(3) Uani 1 2 d S T P . . C2 C 0.06599(14) 0.59322(12) 0.28055(13) 0.0182(3) Uani 1 1 d . . . . . C3 C 0.15450(17) 0.69066(14) 0.31525(16) 0.0236(3) Uani 1 1 d . . . . . H3A H 0.2039 0.6968 0.2611 0.035 Uiso 1 1 calc GR . . . . H3B H 0.2151 0.6814 0.3978 0.035 Uiso 1 1 calc GR . . . . H3C H 0.1027 0.7579 0.3098 0.035 Uiso 1 1 calc GR . . . . C4 C 0.23722(14) 0.44072(13) 0.37280(13) 0.0183(3) Uani 1 1 d . . . . . H4 H 0.2310 0.3582 0.3720 0.022 Uiso 1 1 calc R . . . . C5 C 0.27418(17) 0.47708(15) 0.50313(14) 0.0260(3) Uani 1 1 d . . . . . H5A H 0.2965 0.5559 0.5099 0.039 Uiso 1 1 calc GR . . . . H5B H 0.3495 0.4341 0.5533 0.039 Uiso 1 1 calc GR . . . . H5C H 0.2003 0.4646 0.5299 0.039 Uiso 1 1 calc GR . . . . C6 C 0.33895(16) 0.47061(15) 0.31769(16) 0.0241(3) Uani 1 1 d . . . . . H6A H 0.3087 0.4466 0.2338 0.036 Uiso 1 1 calc GR . . . . H6B H 0.4215 0.4336 0.3622 0.036 Uiso 1 1 calc GR . . . . H6C H 0.3522 0.5509 0.3216 0.036 Uiso 1 1 calc GR . . . . 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 Br1 0.02500(9) 0.02406(10) 0.02194(9) -0.00401(5) 0.00709(6) 0.00160(6) S1 0.0179(2) 0.0128(2) 0.0228(2) 0.000 0.00386(18) 0.000 N1 0.0159(5) 0.0144(5) 0.0176(5) -0.0003(4) 0.0035(4) -0.0004(4) C1 0.0155(8) 0.0130(8) 0.0188(8) 0.000 0.0035(6) 0.000 C2 0.0191(6) 0.0139(6) 0.0199(6) -0.0003(5) 0.0045(5) -0.0005(5) C3 0.0229(7) 0.0149(6) 0.0310(8) -0.0011(6) 0.0071(6) -0.0032(5) C4 0.0154(6) 0.0177(6) 0.0187(6) 0.0006(5) 0.0023(5) 0.0010(5) C5 0.0220(7) 0.0320(8) 0.0198(7) -0.0033(6) 0.0023(5) 0.0013(6) C6 0.0202(7) 0.0238(8) 0.0293(8) 0.0022(6) 0.0098(6) 0.0019(6)