# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_MG7002 _audit_creation_date 07-02-13 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title 'mg7002 in P2(1)/n' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 7.2297(2) _cell_length_b 15.8563(5) _cell_length_c 12.3339(4) _cell_angle_alpha 90 _cell_angle_beta 98.312(2) _cell_angle_gamma 90 _cell_volume 1399.06(7) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328 2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C14 H10 Br2 O3 S1 # Dc = 1.98 Fooo = 816.00 Mu = 59.46 M = 418.11 # Found Formula = C14 H10 Br2 O3 S1 # Dc = 1.98 FOOO = 816.00 Mu = 59.46 M = 418.11 _chemical_formula_sum 'C14 H10 Br2 O3 S1' _chemical_formula_moiety 'C14 H10 Br2 O3 S1' _chemical_compound_source Henj471A _chemical_formula_weight 418.11 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 3 _cell_measurement_theta_max 29 _cell_measurement_temperature 150 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_min 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_max 0.79 _exptl_crystal_density_diffrn 1.985 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 5.946 # Sheldrick geometric approximatio 0.41 0.41 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.41 _exptl_absorpt_correction_T_max 0.41 _diffrn_measurement_device_type 'Bruker SMART' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SMART (Siemens, 1993)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 16386 _reflns_number_total 3430 _diffrn_reflns_av_R_equivalents 0.000 # Number of reflections with Friedels Law is 3430 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3626 _diffrn_reflns_theta_min 2.106 _diffrn_reflns_theta_max 28.726 _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 27.003 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _reflns_limit_h_min -9 _reflns_limit_h_max 9 _reflns_limit_k_min 0 _reflns_limit_k_max 20 _reflns_limit_l_min 0 _reflns_limit_l_max 16 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.39 _refine_diff_density_max 0.56 _refine_ls_number_reflns 3428 _refine_ls_number_restraints 0 _refine_ls_number_parameters 182 #_refine_ls_R_factor_ref 0.0332 _refine_ls_wR_factor_ref 0.0700 _refine_ls_goodness_of_fit_ref 0.7565 #_reflns_number_all 3428 _refine_ls_R_factor_all 0.0332 _refine_ls_wR_factor_all 0.0700 # No actual I/u(I) cutoff was used for refinement. The # threshold below is used for "_gt" information ONLY: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2934 _refine_ls_R_factor_gt 0.0266 _refine_ls_wR_factor_gt 0.0682 _refine_ls_shift/su_max 0.001527 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.00P)^2^ + 0.00P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens C1 C 0.8167(4) 0.66397(17) 0.0197(2) 0.0202 1.0000 Uani . . . . . . C2 C 0.8572(4) 0.75031(17) 0.0135(2) 0.0223 1.0000 Uani . . . . . . C3 C 0.8494(4) 0.79022(17) -0.0863(2) 0.0222 1.0000 Uani . . . . . . C4 C 0.8036(4) 0.74208(17) -0.1816(2) 0.0223 1.0000 Uani . . . . . . C5 C 0.7631(4) 0.65757(17) -0.1763(2) 0.0205 1.0000 Uani . . . . . . C6 C 0.7693(4) 0.61683(16) -0.0748(2) 0.0204 1.0000 Uani . . . . . . C7 C 0.7393(4) 0.48424(17) 0.0148(2) 0.0212 1.0000 Uani . . . . . . C8 C 0.7006(4) 0.39932(17) -0.0074(2) 0.0222 1.0000 Uani . . . . . . C9 C 0.7045(4) 0.34184(17) 0.0772(2) 0.0239 1.0000 Uani . . . . . . C10 C 0.7481(4) 0.37007(19) 0.1854(2) 0.0262 1.0000 Uani . . . . . . C11 C 0.7837(4) 0.45431(18) 0.2072(2) 0.0236 1.0000 Uani . . . . . . C12 C 0.7807(4) 0.51382(16) 0.1220(2) 0.0210 1.0000 Uani . . . . . . C13 C 0.8839(5) 0.88382(17) -0.0956(3) 0.0284 1.0000 Uani . . . . . . C14 C 0.6602(5) 0.25004(17) 0.0531(3) 0.0291 1.0000 Uani . . . . . . Br15 Br 0.69650(4) 0.595008(18) -0.30546(2) 0.0269 1.0000 Uani . . . . . . Br16 Br 0.83182(4) 0.48791(2) 0.35609(2) 0.0299 1.0000 Uani . . . . . . O17 O 0.7279(3) 0.53282(11) -0.07797(16) 0.0248 1.0000 Uani . . . . . . S18 S 0.82109(10) 0.62160(4) 0.15088(5) 0.0225 1.0000 Uani . . . . . . O19 O 0.6667(3) 0.65624(13) 0.19810(17) 0.0307 1.0000 Uani . . . . . . O20 O 1.0053(3) 0.63345(14) 0.21041(17) 0.0340 1.0000 Uani . . . . . . H21 H 0.8926 0.7806 0.0778 0.0263 1.0000 Uiso R . . . . . H41 H 0.8045 0.7678 -0.2494 0.0273 1.0000 Uiso R . . . . . H81 H 0.6664 0.3814 -0.0810 0.0277 1.0000 Uiso R . . . . . H101 H 0.7550 0.3320 0.2435 0.0333 1.0000 Uiso R . . . . . H131 H 0.9644 0.8916 -0.1518 0.0429 1.0000 Uiso R . . . . . H132 H 0.9465 0.9051 -0.0270 0.0432 1.0000 Uiso R . . . . . H133 H 0.7712 0.9122 -0.1155 0.0435 1.0000 Uiso R . . . . . H141 H 0.5859 0.2278 0.1054 0.0454 1.0000 Uiso R . . . . . H142 H 0.7731 0.2197 0.0539 0.0464 1.0000 Uiso R . . . . . H143 H 0.5837 0.2457 -0.0180 0.0454 1.0000 Uiso 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 C1 0.0193(13) 0.0218(13) 0.0197(12) 0.0027(10) 0.0033(10) 0.0004(10) C2 0.0203(13) 0.0208(13) 0.0261(13) -0.0023(10) 0.0040(11) -0.0029(11) C3 0.0177(13) 0.0200(13) 0.0289(14) 0.0006(11) 0.0038(11) 0.0013(10) C4 0.0208(13) 0.0226(13) 0.0237(13) 0.0040(10) 0.0041(11) 0.0023(11) C5 0.0193(13) 0.0216(13) 0.0207(13) -0.0010(10) 0.0034(10) 0.0017(10) C6 0.0182(12) 0.0186(12) 0.0244(13) 0.0005(10) 0.0034(11) -0.0003(10) C7 0.0186(13) 0.0214(12) 0.0240(13) 0.0015(10) 0.0040(11) 0.0010(10) C8 0.0197(13) 0.0215(13) 0.0253(13) 0.0006(11) 0.0036(11) 0.0003(10) C9 0.0179(13) 0.0220(13) 0.0333(15) 0.0042(11) 0.0091(11) 0.0029(10) C10 0.0251(15) 0.0255(14) 0.0289(14) 0.0081(11) 0.0063(12) 0.0015(11) C11 0.0205(13) 0.0283(14) 0.0219(13) 0.0041(11) 0.0029(11) 0.0028(11) C12 0.0177(13) 0.0207(12) 0.0249(13) 0.0013(10) 0.0038(10) 0.0002(10) C13 0.0327(16) 0.0205(13) 0.0320(15) 0.0022(11) 0.0054(13) -0.0033(12) C14 0.0304(16) 0.0196(13) 0.0378(16) 0.0046(12) 0.0071(13) -0.0011(11) Br15 0.03676(17) 0.02318(14) 0.02028(14) -0.00202(11) 0.00282(12) 0.00137(12) Br16 0.03275(17) 0.03614(17) 0.02105(14) 0.00436(12) 0.00438(12) 0.00178(13) O17 0.0349(11) 0.0166(9) 0.0232(9) 0.0004(7) 0.0053(9) -0.0037(8) S18 0.0258(3) 0.0219(3) 0.0196(3) -0.0001(3) 0.0022(3) -0.0037(3) O19 0.0404(13) 0.0281(10) 0.0258(10) -0.0001(8) 0.0123(10) 0.0032(10) O20 0.0340(13) 0.0364(12) 0.0291(11) 0.0037(9) -0.0044(10) -0.0106(10) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.3855(4) loop_ _oxford_twin_element_scale_factors 0.6029(10) 0.3971(10) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . C2 . 1.404(4) yes C1 . C6 . 1.386(4) yes C1 . S18 . 1.748(3) yes C2 . C3 . 1.378(4) yes C2 . H21 . 0.931 no C3 . C4 . 1.401(4) yes C3 . C13 . 1.512(4) yes C4 . C5 . 1.375(4) yes C4 . H41 . 0.931 no C5 . C6 . 1.403(4) yes C5 . Br15 . 1.879(3) yes C6 . O17 . 1.365(3) yes C7 . C8 . 1.394(4) yes C7 . C12 . 1.394(4) yes C7 . O17 . 1.372(3) yes C8 . C9 . 1.383(4) yes C8 . H81 . 0.949 no C9 . C10 . 1.400(4) yes C9 . C14 . 1.511(4) yes C10 . C11 . 1.379(4) yes C10 . H101 . 0.933 no C11 . C12 . 1.410(4) yes C11 . Br16 . 1.896(3) yes C12 . S18 . 1.761(3) yes C13 . H131 . 0.975 no C13 . H132 . 0.961 no C13 . H133 . 0.932 no C14 . H141 . 0.964 no C14 . H142 . 0.947 no C14 . H143 . 0.969 no S18 . O19 . 1.440(2) yes S18 . O20 . 1.437(2) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . C1 . C6 . 120.5(3) yes C2 . C1 . S18 . 116.7(2) yes C6 . C1 . S18 . 122.7(2) yes C1 . C2 . C3 . 121.0(3) yes C1 . C2 . H21 . 119.3 no C3 . C2 . H21 . 119.7 no C2 . C3 . C4 . 118.3(2) yes C2 . C3 . C13 . 122.2(3) yes C4 . C3 . C13 . 119.5(3) yes C3 . C4 . C5 . 121.1(3) yes C3 . C4 . H41 . 118.9 no C5 . C4 . H41 . 119.9 no C4 . C5 . C6 . 120.8(3) yes C4 . C5 . Br15 . 120.3(2) yes C6 . C5 . Br15 . 119.0(2) yes C5 . C6 . C1 . 118.3(2) yes C5 . C6 . O17 . 116.5(2) yes C1 . C6 . O17 . 125.2(2) yes C8 . C7 . C12 . 121.4(2) yes C8 . C7 . O17 . 113.1(2) yes C12 . C7 . O17 . 125.5(2) yes C7 . C8 . C9 . 120.5(3) yes C7 . C8 . H81 . 119.6 no C9 . C8 . H81 . 119.9 no C8 . C9 . C10 . 119.1(3) yes C8 . C9 . C14 . 120.4(3) yes C10 . C9 . C14 . 120.5(3) yes C9 . C10 . C11 . 120.4(3) yes C9 . C10 . H101 . 120.3 no C11 . C10 . H101 . 119.3 no C10 . C11 . C12 . 121.4(3) yes C10 . C11 . Br16 . 117.6(2) yes C12 . C11 . Br16 . 121.0(2) yes C11 . C12 . C7 . 117.4(2) yes C11 . C12 . S18 . 120.9(2) yes C7 . C12 . S18 . 121.7(2) yes C3 . C13 . H131 . 107.5 no C3 . C13 . H132 . 109.9 no H131 . C13 . H132 . 109.1 no C3 . C13 . H133 . 110.2 no H131 . C13 . H133 . 109.9 no H132 . C13 . H133 . 110.2 no C9 . C14 . H141 . 110.1 no C9 . C14 . H142 . 109.2 no H141 . C14 . H142 . 111.7 no C9 . C14 . H143 . 108.9 no H141 . C14 . H143 . 106.2 no H142 . C14 . H143 . 110.6 no C7 . O17 . C6 . 122.6(2) yes C12 . S18 . C1 . 101.84(13) yes C12 . S18 . O19 . 109.66(13) yes C1 . S18 . O19 . 108.44(13) yes C12 . S18 . O20 . 110.16(13) yes C1 . S18 . O20 . 108.31(13) yes O19 . S18 . O20 . 117.29(13) yes _database_code_depnum_ccdc_archive 'CCDC 945230'