# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics # This journal is © The Owner Societies 2012 data_global _journal_name_full Phys.Chem.Chem.Phys.(PCCP) _journal_coden_cambridge 1326 #TrackingRef '- DTP structures.cif' _audit_creation_method 'APEX2 v2010.5-0' _publ_contact_author_name 'Seth Rasmussen' _publ_contact_author_address ; Department of Chemistry and Biochemistry North Dakota State University NDSU Dept. 2735, P.O. Box 6050 Fargo, ND 58108-6050 ; _publ_contact_author_email seth.rasmussen@ndsu.edu _publ_contact_author_phone '701 231-8747' loop_ _publ_author_name S.Evenson T.Pappenfus C.Delgado K.Radke-Wohlers T.J.Navarrete S.Rasmussen data_mo_sxe3_0ma _database_code_depnum_ccdc_archive 'CCDC 863469' #TrackingRef '- DTP structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-phenyldithieno[3,2-b:2',3'-d]pyrrole ; _chemical_name_common N-phenyldithienopyrrole _chemical_melting_point 125 _chemical_formula_moiety 'C14 H9 N S2' _chemical_formula_sum 'C14 H9 N S2' _chemical_formula_weight 255.34 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _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 9.9552(11) _cell_length_b 14.2894(16) _cell_length_c 8.1057(9) _cell_angle_alpha 90.00 _cell_angle_beta 101.783(2) _cell_angle_gamma 90.00 _cell_volume 1128.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6007 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 27.90 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.503 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.443 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8532 _exptl_absorpt_correction_T_max 0.9365 _exptl_absorpt_process_details 'Acta Cryst (1995). A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9952 _diffrn_reflns_av_R_equivalents 0.0167 _diffrn_reflns_av_sigmaI/netI 0.0167 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 27.92 _reflns_number_total 2707 _reflns_number_gt 2465 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. ; _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^)+(0.0375P)^2^+0.5674P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2707 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0298 _refine_ls_R_factor_gt 0.0267 _refine_ls_wR_factor_ref 0.0721 _refine_ls_wR_factor_gt 0.0699 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _iucr_refine_instructions_details ; THE LAST RES FILE TITL mo_sxe3_0ma in P2(1)/c CELL 0.71073 9.9552 14.2894 8.1057 90.000 101.783 90.000 ZERR 4.00 0.0011 0.0016 0.0009 0.000 0.002 0.000 LATT 1 SYMM -x, y+1/2, -z+1/2 SFAC C H N S UNIT 56 36 4 8 TEMP -173.140 SIZE 0.150 0.195 0.370 ACTA L.S. 4 FMAP 2 PLAN 5 BOND $H WGHT 0.037500 0.567400 FVAR 0.16928 S1 4 0.014546 0.630726 -0.142369 11.00000 0.01567 0.01321 = 0.01577 -0.00035 0.00285 0.00245 S2 4 0.075784 0.403756 -0.434968 11.00000 0.01984 0.01577 = 0.01247 -0.00169 0.00078 0.00177 N1 3 0.291664 0.446170 0.005709 11.00000 0.01446 0.01309 = 0.01254 -0.00055 0.00186 0.00080 C1 1 0.609246 0.346696 0.389478 11.00000 0.01893 0.01705 = 0.01900 0.00212 -0.00248 -0.00103 AFIX 43 H1 2 0.680982 0.323929 0.475929 11.00000 -1.20000 AFIX 0 C2 1 0.620578 0.341000 0.221583 11.00000 0.01532 0.01672 = 0.02192 0.00088 0.00215 0.00057 AFIX 43 H2 2 0.700057 0.313827 0.193450 11.00000 -1.20000 AFIX 0 C3 1 0.516360 0.374809 0.094672 11.00000 0.01576 0.01646 = 0.01593 0.00028 0.00379 -0.00135 AFIX 43 H3 2 0.525044 0.371563 -0.019746 11.00000 -1.20000 AFIX 0 C4 1 0.398991 0.413518 0.136162 11.00000 0.01361 0.01153 = 0.01540 0.00126 0.00072 -0.00143 C5 1 0.208262 0.523880 0.011163 11.00000 0.01356 0.01280 = 0.01464 0.00018 0.00361 -0.00062 C6 1 0.113382 0.531547 -0.140374 11.00000 0.01389 0.01230 = 0.01442 0.00028 0.00359 0.00053 C7 1 0.138670 0.456397 -0.243803 11.00000 0.01550 0.01304 = 0.01258 -0.00072 0.00277 -0.00081 C8 1 0.202438 0.598319 0.125843 11.00000 0.01732 0.01581 = 0.01552 -0.00267 0.00300 -0.00112 AFIX 43 H8 2 0.260223 0.603922 0.234207 11.00000 -1.20000 AFIX 0 C9 1 0.102258 0.660604 0.058541 11.00000 0.02004 0.01474 = 0.01725 -0.00356 0.00439 -0.00086 AFIX 43 H9 2 0.082375 0.715153 0.116145 11.00000 -1.20000 AFIX 0 C10 1 0.492257 0.385927 0.430125 11.00000 0.02213 0.01645 = 0.01443 -0.00057 0.00151 -0.00369 AFIX 43 H10 2 0.484648 0.390344 0.544801 11.00000 -1.20000 AFIX 0 C11 1 0.386239 0.418763 0.303948 11.00000 0.01661 0.01413 = 0.01607 -0.00089 0.00422 -0.00190 AFIX 43 H11 2 0.305844 0.444540 0.332038 11.00000 -1.20000 AFIX 0 C12 1 0.248242 0.405476 -0.152227 11.00000 0.01399 0.01315 = 0.01351 -0.00014 0.00370 -0.00102 C13 1 0.282149 0.323811 -0.235941 11.00000 0.01712 0.01255 = 0.01710 0.00071 0.00606 0.00095 AFIX 43 H13 2 0.353725 0.281395 -0.190798 11.00000 -1.20000 AFIX 0 C14 1 0.197190 0.315190 -0.390186 11.00000 0.02065 0.01250 = 0.01753 -0.00157 0.00591 0.00089 AFIX 43 H14 2 0.203831 0.265455 -0.465885 11.00000 -1.20000 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM mo_sxe3_0ma in P2(1)/c REM R1 = 0.0267 for 2465 Fo > 4sig(Fo) and 0.0298 for all 2707 data REM 154 parameters refined using 0 restraints END WGHT 0.0371 0.5682 REM Highest difference peak 0.359, deepest hole -0.261, 1-sigma level 0.053 Q1 1 0.1541 0.5242 -0.0615 11.00000 0.05 0.36 Q2 1 0.1840 0.4239 -0.1979 11.00000 0.05 0.33 Q3 1 0.3928 0.4225 0.2239 11.00000 0.05 0.33 Q4 1 0.2099 0.5535 0.0789 11.00000 0.05 0.31 Q5 1 0.3465 0.4305 0.0635 11.00000 0.05 0.30 ; 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 0.01455(3) 0.63073(2) -0.14237(4) 0.01493(9) Uani 1 1 d . . . S2 S 0.07578(3) 0.40376(2) -0.43497(4) 0.01639(9) Uani 1 1 d . . . N1 N 0.29166(10) 0.44617(7) 0.00571(12) 0.0135(2) Uani 1 1 d . . . C1 C 0.60925(13) 0.34670(9) 0.38948(16) 0.0192(3) Uani 1 1 d . . . H1 H 0.6810 0.3239 0.4759 0.023 Uiso 1 1 calc R . . C2 C 0.62058(13) 0.34100(9) 0.22158(17) 0.0182(3) Uani 1 1 d . . . H2 H 0.7001 0.3138 0.1934 0.022 Uiso 1 1 calc R . . C3 C 0.51636(13) 0.37481(8) 0.09467(16) 0.0160(2) Uani 1 1 d . . . H3 H 0.5250 0.3716 -0.0197 0.019 Uiso 1 1 calc R . . C4 C 0.39899(12) 0.41352(8) 0.13616(15) 0.0138(2) Uani 1 1 d . . . C5 C 0.20826(12) 0.52388(8) 0.01116(15) 0.0136(2) Uani 1 1 d . . . C6 C 0.11338(12) 0.53155(8) -0.14037(15) 0.0134(2) Uani 1 1 d . . . C7 C 0.13867(12) 0.45640(8) -0.24380(15) 0.0137(2) Uani 1 1 d . . . C8 C 0.20244(13) 0.59832(9) 0.12584(16) 0.0163(2) Uani 1 1 d . . . H8 H 0.2602 0.6039 0.2342 0.020 Uiso 1 1 calc R . . C9 C 0.10226(13) 0.66060(9) 0.05854(16) 0.0173(2) Uani 1 1 d . . . H9 H 0.0824 0.7152 0.1161 0.021 Uiso 1 1 calc R . . C10 C 0.49226(14) 0.38593(9) 0.43012(16) 0.0180(3) Uani 1 1 d . . . H10 H 0.4846 0.3903 0.5448 0.022 Uiso 1 1 calc R . . C11 C 0.38624(13) 0.41876(8) 0.30395(15) 0.0155(2) Uani 1 1 d . . . H11 H 0.3058 0.4445 0.3320 0.019 Uiso 1 1 calc R . . C12 C 0.24824(12) 0.40548(8) -0.15223(15) 0.0134(2) Uani 1 1 d . . . C13 C 0.28215(12) 0.32381(8) -0.23594(15) 0.0152(2) Uani 1 1 d . . . H13 H 0.3537 0.2814 -0.1908 0.018 Uiso 1 1 calc R . . C14 C 0.19719(13) 0.31519(9) -0.39019(16) 0.0166(2) Uani 1 1 d . . . H14 H 0.2038 0.2655 -0.4659 0.020 Uiso 1 1 calc 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 0.01567(15) 0.01321(15) 0.01577(16) -0.00035(11) 0.00285(11) 0.00245(10) S2 0.01984(16) 0.01577(16) 0.01247(15) -0.00169(11) 0.00078(11) 0.00177(11) N1 0.0145(5) 0.0131(5) 0.0125(5) -0.0006(4) 0.0019(4) 0.0008(4) C1 0.0189(6) 0.0171(6) 0.0190(6) 0.0021(5) -0.0025(5) -0.0010(5) C2 0.0153(6) 0.0167(6) 0.0219(6) 0.0009(5) 0.0021(5) 0.0006(5) C3 0.0158(6) 0.0165(6) 0.0159(6) 0.0003(5) 0.0038(5) -0.0013(4) C4 0.0136(5) 0.0115(5) 0.0154(6) 0.0013(4) 0.0007(4) -0.0014(4) C5 0.0136(5) 0.0128(5) 0.0146(5) 0.0002(4) 0.0036(4) -0.0006(4) C6 0.0139(5) 0.0123(5) 0.0144(5) 0.0003(4) 0.0036(4) 0.0005(4) C7 0.0155(5) 0.0130(5) 0.0126(5) -0.0007(4) 0.0028(4) -0.0008(4) C8 0.0173(6) 0.0158(6) 0.0155(6) -0.0027(5) 0.0030(5) -0.0011(5) C9 0.0200(6) 0.0147(6) 0.0172(6) -0.0036(5) 0.0044(5) -0.0009(5) C10 0.0221(6) 0.0165(6) 0.0144(6) -0.0006(5) 0.0015(5) -0.0037(5) C11 0.0166(6) 0.0141(5) 0.0161(6) -0.0009(5) 0.0042(5) -0.0019(4) C12 0.0140(5) 0.0131(6) 0.0135(5) -0.0001(4) 0.0037(4) -0.0010(4) C13 0.0171(6) 0.0126(5) 0.0171(6) 0.0007(5) 0.0061(5) 0.0010(4) C14 0.0206(6) 0.0125(5) 0.0175(6) -0.0016(5) 0.0059(5) 0.0009(5) _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 C6 1.7235(12) . ? S1 C9 1.7367(13) . ? S2 C7 1.7212(12) . ? S2 C14 1.7364(13) . ? N1 C12 1.3921(15) . ? N1 C5 1.3926(15) . ? N1 C4 1.4199(15) . ? C1 C2 1.3907(19) . ? C1 C10 1.3914(19) . ? C1 H1 0.9500 . ? C2 C3 1.3900(17) . ? C2 H2 0.9500 . ? C3 C4 1.3945(17) . ? C3 H3 0.9500 . ? C4 C11 1.3935(17) . ? C5 C6 1.3925(16) . ? C5 C8 1.4216(17) . ? C6 C7 1.4162(16) . ? C7 C12 1.3927(17) . ? C8 C9 1.3646(18) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C11 1.3926(18) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.4247(17) . ? C13 C14 1.3645(17) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? 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 C6 S1 C9 90.95(6) . . ? C7 S2 C14 91.18(6) . . ? C12 N1 C5 106.68(10) . . ? C12 N1 C4 126.35(10) . . ? C5 N1 C4 126.96(10) . . ? C2 C1 C10 119.63(12) . . ? C2 C1 H1 120.2 . . ? C10 C1 H1 120.2 . . ? C3 C2 C1 120.43(12) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 119.66(12) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C11 C4 C3 120.30(11) . . ? C11 C4 N1 120.30(11) . . ? C3 C4 N1 119.40(11) . . ? C6 C5 N1 109.64(10) . . ? C6 C5 C8 114.02(11) . . ? N1 C5 C8 136.18(11) . . ? C5 C6 C7 106.98(10) . . ? C5 C6 S1 110.86(9) . . ? C7 C6 S1 142.01(10) . . ? C12 C7 C6 107.17(10) . . ? C12 C7 S2 110.66(9) . . ? C6 C7 S2 142.03(10) . . ? C9 C8 C5 110.53(11) . . ? C9 C8 H8 124.7 . . ? C5 C8 H8 124.7 . . ? C8 C9 S1 113.64(10) . . ? C8 C9 H9 123.2 . . ? S1 C9 H9 123.2 . . ? C1 C10 C11 120.49(12) . . ? C1 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C10 C11 C4 119.49(11) . . ? C10 C11 H11 120.3 . . ? C4 C11 H11 120.3 . . ? N1 C12 C7 109.53(10) . . ? N1 C12 C13 136.13(11) . . ? C7 C12 C13 114.21(11) . . ? C14 C13 C12 110.34(11) . . ? C14 C13 H13 124.8 . . ? C12 C13 H13 124.8 . . ? C13 C14 S2 113.61(9) . . ? C13 C14 H14 123.2 . . ? S2 C14 H14 123.2 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.92 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.359 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.053 data_cu_sxe2_0ma _database_code_depnum_ccdc_archive 'CCDC 863470' #TrackingRef '- DTP structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-Phenyl-2,6-bis(2-thienyl)dithieno[3,2-b:2?3?-d]pyrrole ; _chemical_name_common ? _chemical_melting_point 193 _chemical_formula_moiety 'C22 H13 N S4' _chemical_formula_sum 'C22 H13 N S4' _chemical_formula_weight 419.57 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna2(1) _space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 10.8666(3) _cell_length_b 22.8858(6) _cell_length_c 7.4246(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1846.43(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4624 _cell_measurement_theta_min 4.50 _cell_measurement_theta_max 67.25 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max .374 _exptl_crystal_size_mid .077 _exptl_crystal_size_min .031 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.509 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 4.774 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6322 _exptl_absorpt_correction_T_max 0.7529 _exptl_absorpt_process_details 'Acta Cryst (1995). A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6775 _diffrn_reflns_av_R_equivalents 0.0292 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.86 _diffrn_reflns_theta_max 67.33 _reflns_number_total 2525 _reflns_number_gt 2437 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. ; _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^)+(0.0556P)^2^+0.0787P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.032(17) _refine_ls_number_reflns 2525 _refine_ls_number_parameters 254 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0320 _refine_ls_R_factor_gt 0.0306 _refine_ls_wR_factor_ref 0.0809 _refine_ls_wR_factor_gt 0.0796 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.002 _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 0.43457(5) 0.55731(2) 1.23164(10) 0.01977(18) Uani 1 1 d . . . S2 S 0.44320(6) 0.37546(2) 1.24143(11) 0.02173(18) Uani 1 1 d . . . C2 C 0.3598(2) 0.66618(11) 1.1000(4) 0.0188(6) Uani 1 1 d . . . C3 C 0.3539(2) 0.60295(10) 1.0818(4) 0.0169(5) Uani 1 1 d . D . C4 C 0.3824(2) 0.49576(10) 1.1178(4) 0.0171(6) Uani 1 1 d . . . C5 C 0.3795(2) 0.43404(11) 1.1285(4) 0.0190(6) Uani 1 1 d . . . C6 C 0.3694(2) 0.32604(10) 1.0962(4) 0.0191(6) Uani 1 1 d . C . C7 C 0.3944(2) 0.26416(11) 1.1097(4) 0.0205(6) Uani 1 1 d . . . C8 C 0.4978(9) 0.2367(4) 1.1928(16) 0.037(4) Uani 1 1 d . C . H8 H 0.5603 0.2568 1.2575 0.044 Uiso 1 1 calc R . . C9 C 0.4943(3) 0.17541(13) 1.1658(5) 0.0325(8) Uani 1 1 d . . . H9 H 0.5560 0.1496 1.2091 0.039 Uiso 1 1 calc R C . C10 C 0.3154(2) 0.77099(12) 1.0758(4) 0.0253(6) Uani 1 1 d . . . H10 H 0.2825 0.8087 1.0517 0.030 Uiso 1 1 calc R A 3 C11 C 0.3042(2) 0.41457(10) 0.9884(4) 0.0166(5) Uani 1 1 d . C . C12 C 0.4505(5) 0.7007(3) 1.1889(10) 0.0271(16) Uani 1 1 d . D . H12 H 0.5197 0.6858 1.2519 0.032 Uiso 1 1 calc R . . C13 C 0.1914(2) 0.46022(10) 0.7306(5) 0.0169(6) Uani 1 1 d . C . C14 C 0.2211(2) 0.49684(11) 0.5865(4) 0.0190(6) Uani 1 1 d . . . H14 H 0.2894 0.5226 0.5954 0.023 Uiso 1 1 calc R . . C15 C 0.1509(3) 0.49567(11) 0.4307(4) 0.0236(7) Uani 1 1 d . . . H15 H 0.1701 0.5211 0.3336 0.028 Uiso 1 1 calc R . . C16 C 0.0524(3) 0.45718(11) 0.4167(5) 0.0266(7) Uani 1 1 d . . . H16 H 0.0037 0.4565 0.3104 0.032 Uiso 1 1 calc R . . C17 C 0.0252(2) 0.41975(11) 0.5583(5) 0.0248(7) Uani 1 1 d . . . H17 H -0.0406 0.3927 0.5469 0.030 Uiso 1 1 calc R . . C18 C 0.0928(2) 0.42147(10) 0.7155(4) 0.0199(6) Uani 1 1 d . . . H18 H 0.0724 0.3964 0.8130 0.024 Uiso 1 1 calc R . . C19 C 0.3087(2) 0.51182(10) 0.9729(4) 0.0167(6) Uani 1 1 d . C . C20 C 0.2920(2) 0.57288(11) 0.9524(4) 0.0181(6) Uani 1 1 d . . . H20 H 0.2438 0.5905 0.8604 0.022 Uiso 1 1 calc R D . C21 C 0.2973(2) 0.35345(10) 0.9708(4) 0.0176(6) Uani 1 1 d . . . H21 H 0.2490 0.3337 0.8833 0.021 Uiso 1 1 calc R C . C22 C 0.3953(3) 0.15738(12) 1.0729(5) 0.0347(8) Uani 1 1 d . C . H22 H 0.3793 0.1176 1.0448 0.042 Uiso 1 1 calc R B 1 S3 S 0.30179(6) 0.21338(3) 1.01111(13) 0.0232(2) Uani 0.904(3) 1 d P C 1 S31 S 0.5060(17) 0.2351(7) 1.191(3) 0.003(4) Uiso 0.096(3) 1 d P C 2 S4 S 0.24880(6) 0.70897(3) 1.00798(13) 0.0228(2) Uani 0.870(2) 1 d P D 3 S41 S 0.4775(9) 0.7005(5) 1.1972(16) 0.0070(19) Uiso 0.130(2) 1 d P D 4 N1 N 0.25995(19) 0.46229(9) 0.8920(4) 0.0176(5) Uani 1 1 d . . . C1 C 0.4211(2) 0.76208(12) 1.1686(5) 0.0254(7) Uani 1 1 d . D . H1 H 0.4706 0.7928 1.2154 0.030 Uiso 1 1 calc 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 0.0224(3) 0.0173(3) 0.0196(4) -0.0015(3) -0.0044(3) -0.0031(2) S2 0.0269(3) 0.0175(3) 0.0208(4) 0.0019(3) -0.0085(3) -0.0006(2) C2 0.0194(12) 0.0177(11) 0.0194(16) 0.0001(11) 0.0032(11) -0.0016(9) C3 0.0109(11) 0.0190(12) 0.0208(15) -0.0015(11) 0.0015(11) -0.0023(9) C4 0.0158(13) 0.0189(12) 0.0164(16) -0.0031(11) -0.0015(11) -0.0023(9) C5 0.0184(13) 0.0207(13) 0.0178(16) 0.0044(11) -0.0017(11) -0.0003(10) C6 0.0179(12) 0.0185(12) 0.0210(16) 0.0004(12) 0.0010(12) -0.0019(9) C7 0.0202(13) 0.0197(13) 0.0216(17) 0.0013(12) 0.0018(12) 0.0002(10) C8 0.035(5) 0.042(4) 0.034(4) 0.0088(18) -0.003(2) -0.0020(18) C9 0.0309(16) 0.0305(15) 0.0360(19) 0.0142(14) 0.0094(15) 0.0114(12) C10 0.0297(14) 0.0197(13) 0.0264(17) 0.0007(12) 0.0077(14) 0.0055(10) C11 0.0148(11) 0.0160(11) 0.0189(15) 0.0019(12) 0.0003(12) -0.0002(8) C12 0.022(3) 0.0223(18) 0.037(3) -0.0058(14) -0.004(3) 0.003(2) C13 0.0152(11) 0.0170(11) 0.0185(16) -0.0040(11) -0.0040(13) 0.0029(8) C14 0.0186(12) 0.0182(12) 0.0203(15) -0.0010(11) -0.0007(12) 0.0013(10) C15 0.0276(15) 0.0219(13) 0.0213(16) -0.0001(12) -0.0019(13) 0.0072(10) C16 0.0285(15) 0.0198(12) 0.032(2) -0.0077(13) -0.0118(14) 0.0064(10) C17 0.0191(12) 0.0198(12) 0.0355(19) -0.0039(12) -0.0095(13) 0.0001(10) C18 0.0180(12) 0.0177(11) 0.0241(17) -0.0011(12) -0.0016(13) -0.0006(9) C19 0.0177(12) 0.0143(11) 0.0180(17) 0.0006(11) 0.0014(12) -0.0021(9) C20 0.0157(11) 0.0181(12) 0.0204(16) 0.0003(11) 0.0013(12) 0.0006(9) C21 0.0175(12) 0.0164(11) 0.0188(17) 0.0015(12) -0.0024(12) -0.0030(9) C22 0.0528(19) 0.0176(13) 0.034(2) -0.0042(13) 0.0195(18) -0.0041(12) S3 0.0263(4) 0.0187(3) 0.0245(5) -0.0011(3) -0.0027(4) -0.0017(2) S4 0.0251(4) 0.0189(3) 0.0243(5) -0.0014(3) -0.0001(4) 0.0008(2) N1 0.0163(11) 0.0169(11) 0.0197(15) 0.0002(9) -0.0019(10) -0.0013(8) C1 0.0277(14) 0.0226(13) 0.0258(18) -0.0074(12) 0.0058(13) -0.0084(11) _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 C4 1.738(3) . ? S1 C3 1.759(3) . ? S2 C5 1.726(3) . ? S2 C6 1.757(3) . ? C2 C12 1.425(6) . ? C2 C3 1.455(3) . ? C2 S41 1.664(11) . ? C2 S4 1.698(3) . ? C3 C20 1.361(4) . ? C4 C19 1.391(4) . ? C4 C5 1.415(4) . ? C5 C11 1.397(4) . ? C6 C21 1.369(4) . ? C6 C7 1.446(3) . ? C7 C8 1.427(10) . ? C7 S31 1.508(19) . ? C7 S3 1.703(3) . ? C8 C9 1.418(10) . ? C8 H8 0.9500 . ? C9 C22 1.343(5) . ? C9 H9 0.9500 . ? C10 C1 1.355(4) . ? C10 S4 1.671(3) . ? C10 H10 0.9500 . ? C11 N1 1.391(3) . ? C11 C21 1.407(3) . ? C12 C1 1.447(6) . ? C12 H12 0.9500 . ? C13 C18 1.395(3) . ? C13 C14 1.396(4) . ? C13 N1 1.412(4) . ? C14 C15 1.386(4) . ? C14 H14 0.9500 . ? C15 C16 1.390(4) . ? C15 H15 0.9500 . ? C16 C17 1.388(5) . ? C16 H16 0.9500 . ? C17 C18 1.380(4) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 N1 1.388(3) . ? C19 C20 1.417(3) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 S3 1.699(3) . ? C22 H22 0.9500 . ? C1 H1 0.9500 . ? 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 C4 S1 C3 90.65(12) . . ? C5 S2 C6 91.07(13) . . ? C12 C2 C3 128.7(3) . . ? C12 C2 S41 6.7(6) . . ? C3 C2 S41 122.9(4) . . ? C12 C2 S4 111.0(3) . . ? C3 C2 S4 120.3(2) . . ? S41 C2 S4 116.7(4) . . ? C20 C3 C2 126.2(3) . . ? C20 C3 S1 113.14(18) . . ? C2 C3 S1 120.7(2) . . ? C19 C4 C5 107.1(2) . . ? C19 C4 S1 110.47(18) . . ? C5 C4 S1 142.1(2) . . ? C11 C5 C4 106.8(2) . . ? C11 C5 S2 110.44(18) . . ? C4 C5 S2 142.5(2) . . ? C21 C6 C7 127.1(3) . . ? C21 C6 S2 112.56(18) . . ? C7 C6 S2 120.2(2) . . ? C8 C7 C6 127.5(5) . . ? C8 C7 S31 2.1(11) . . ? C6 C7 S31 127.7(6) . . ? C8 C7 S3 110.6(4) . . ? C6 C7 S3 121.8(2) . . ? S31 C7 S3 110.2(6) . . ? C9 C8 C7 110.7(7) . . ? C9 C8 H8 124.7 . . ? C7 C8 H8 124.7 . . ? C22 C9 C8 113.5(5) . . ? C22 C9 H9 123.3 . . ? C8 C9 H9 123.3 . . ? C1 C10 S4 113.1(2) . . ? C1 C10 H10 123.4 . . ? S4 C10 H10 123.4 . . ? N1 C11 C5 109.6(2) . . ? N1 C11 C21 135.6(3) . . ? C5 C11 C21 114.6(2) . . ? C2 C12 C1 109.7(4) . . ? C2 C12 H12 125.1 . . ? C1 C12 H12 125.1 . . ? C18 C13 C14 119.9(3) . . ? C18 C13 N1 119.6(3) . . ? C14 C13 N1 120.5(2) . . ? C15 C14 C13 120.0(2) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 119.9(3) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C17 C16 C15 119.9(3) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C18 C17 C16 120.7(2) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C18 C13 119.7(3) . . ? C17 C18 H18 120.2 . . ? C13 C18 H18 120.2 . . ? N1 C19 C4 109.8(2) . . ? N1 C19 C20 135.2(3) . . ? C4 C19 C20 114.7(2) . . ? C3 C20 C19 111.1(2) . . ? C3 C20 H20 124.5 . . ? C19 C20 H20 124.5 . . ? C6 C21 C11 111.3(2) . . ? C6 C21 H21 124.4 . . ? C11 C21 H21 124.4 . . ? C9 C22 S3 112.7(2) . . ? C9 C22 H22 123.6 . . ? S3 C22 H22 123.6 . . ? C22 S3 C7 92.59(15) . . ? C10 S4 C2 93.49(13) . . ? C19 N1 C11 106.7(2) . . ? C19 N1 C13 126.6(2) . . ? C11 N1 C13 126.3(2) . . ? C10 C1 C12 112.7(3) . . ? C10 C1 H1 123.7 . . ? C12 C1 H1 123.7 . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 67.33 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.653 _refine_diff_density_min -0.257 _refine_diff_density_rms 0.063 data_mo_sxe1_0m _database_code_depnum_ccdc_archive 'CCDC 863471' #TrackingRef '- DTP structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,6-Dibromo-N-octanoyldithieno[3,2-b:2',3'-d]pyrrole ; _chemical_name_common 2,6-Dibromo-N-octanoyldithienopyrrole _chemical_melting_point 99 _chemical_formula_moiety 'C16 H17 Br2 N O S2' _chemical_formula_sum 'C16 H17 Br2 N O S2' _chemical_formula_weight 463.25 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' O O 0.0106 0.0060 '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 _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 8.9068(6) _cell_length_b 21.4647(14) _cell_length_c 9.5892(6) _cell_angle_alpha 90.00 _cell_angle_beta 108.7260(10) _cell_angle_gamma 90.00 _cell_volume 1736.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8247 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 27.56 _exptl_crystal_description parallelepiped _exptl_crystal_colour orange _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.772 _exptl_crystal_density_method none _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 4.910 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4713 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details 'Acta Cryst (1995). A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 15990 _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_sigmaI/netI 0.0207 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 27.59 _reflns_number_total 4003 _reflns_number_gt 3622 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. ; _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^)+(0.0174P)^2^+0.8820P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4003 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0218 _refine_ls_R_factor_gt 0.0179 _refine_ls_wR_factor_ref 0.0429 _refine_ls_wR_factor_gt 0.0416 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.001 _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 Br1 Br 0.382737(18) 0.173127(8) 0.292632(17) 0.01756(5) Uani 1 1 d . . . Br2 Br 0.823734(18) 0.573934(7) 0.073871(18) 0.01679(5) Uani 1 1 d . . . S1 S 0.61716(4) 0.479829(18) 0.18277(4) 0.01391(8) Uani 1 1 d . . . S2 S 0.43536(4) 0.314565(19) 0.26633(4) 0.01600(8) Uani 1 1 d . . . N N 0.75559(15) 0.32235(6) 0.07723(14) 0.0136(3) Uani 1 1 d . . . O O 0.93710(14) 0.32638(5) -0.04160(14) 0.0227(3) Uani 1 1 d . . . C1 C 0.48556(18) 0.23923(8) 0.23348(18) 0.0162(3) Uani 1 1 d . . . C2 C 0.60019(18) 0.23474(7) 0.16744(18) 0.0154(3) Uani 1 1 d . . . H2 H 0.6402 0.1969 0.1417 0.018 Uiso 1 1 calc R . . C3 C 0.65005(17) 0.29559(7) 0.14340(17) 0.0135(3) Uani 1 1 d . . . C4 C 0.86232(18) 0.29393(7) 0.01560(17) 0.0151(3) Uani 1 1 d . . . C5 C 0.87725(18) 0.22411(7) 0.02704(17) 0.0147(3) Uani 1 1 d . . . H5A H 0.7733 0.2050 -0.0256 0.018 Uiso 1 1 calc R . . H5B H 0.9068 0.2118 0.1319 0.018 Uiso 1 1 calc R . . C6 C 1.00158(18) 0.19924(7) -0.03795(18) 0.0151(3) Uani 1 1 d . . . H6A H 0.9740 0.2130 -0.1417 0.018 Uiso 1 1 calc R . . H6B H 1.1062 0.2173 0.0171 0.018 Uiso 1 1 calc R . . C7 C 1.01377(18) 0.12844(7) -0.03208(18) 0.0147(3) Uani 1 1 d . . . H7A H 0.9090 0.1104 -0.0862 0.018 Uiso 1 1 calc R . . H7B H 1.0425 0.1147 0.0717 0.018 Uiso 1 1 calc R . . C8 C 1.13655(18) 0.10381(7) -0.09842(18) 0.0157(3) Uani 1 1 d . . . H8A H 1.1068 0.1173 -0.2025 0.019 Uiso 1 1 calc R . . H8B H 1.2408 0.1226 -0.0452 0.019 Uiso 1 1 calc R . . C9 C 1.15278(18) 0.03307(8) -0.09190(18) 0.0164(3) Uani 1 1 d . . . H9A H 1.0501 0.0143 -0.1495 0.020 Uiso 1 1 calc R . . H9B H 1.1774 0.0194 0.0116 0.020 Uiso 1 1 calc R . . C10 C 1.2823(2) 0.00902(8) -0.1519(2) 0.0205(3) Uani 1 1 d . . . H10A H 1.2565 0.0221 -0.2560 0.025 Uiso 1 1 calc R . . H10B H 1.3845 0.0286 -0.0957 0.025 Uiso 1 1 calc R . . C11 C 1.3015(2) -0.06159(8) -0.1429(2) 0.0248(4) Uani 1 1 d . . . H11A H 1.3263 -0.0750 -0.0403 0.037 Uiso 1 1 calc R . . H11B H 1.3878 -0.0739 -0.1798 0.037 Uiso 1 1 calc R . . H11C H 1.2026 -0.0813 -0.2029 0.037 Uiso 1 1 calc R . . C12 C 0.75939(17) 0.49257(7) 0.09729(17) 0.0145(3) Uani 1 1 d . . . C13 C 0.63006(17) 0.40093(7) 0.15624(17) 0.0136(3) Uani 1 1 d . . . C14 C 0.74029(17) 0.38729(7) 0.08647(17) 0.0138(3) Uani 1 1 d . . . C15 C 0.81593(17) 0.44035(7) 0.05080(17) 0.0147(3) Uani 1 1 d . . . H15 H 0.8936 0.4395 0.0022 0.018 Uiso 1 1 calc R . . C16 C 0.57284(17) 0.34312(7) 0.19132(16) 0.0132(3) Uani 1 1 d . . . 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 0.01801(8) 0.01688(9) 0.01866(9) 0.00275(6) 0.00708(6) -0.00463(6) Br2 0.01894(8) 0.01027(8) 0.02487(9) -0.00126(6) 0.01221(6) -0.00033(5) S1 0.01484(17) 0.01217(18) 0.01682(19) -0.00060(14) 0.00804(14) 0.00112(13) S2 0.01617(18) 0.0158(2) 0.0191(2) 0.00164(15) 0.01002(15) -0.00001(14) N 0.0159(6) 0.0106(6) 0.0167(7) 0.0002(5) 0.0087(5) 0.0000(5) O 0.0269(6) 0.0152(6) 0.0349(7) 0.0005(5) 0.0223(6) -0.0003(5) C1 0.0171(7) 0.0138(8) 0.0178(8) 0.0019(6) 0.0056(6) -0.0025(6) C2 0.0172(7) 0.0134(8) 0.0158(8) 0.0006(6) 0.0057(6) -0.0003(6) C3 0.0136(7) 0.0151(8) 0.0123(7) 0.0012(6) 0.0049(6) -0.0003(6) C4 0.0157(7) 0.0149(8) 0.0161(8) -0.0015(6) 0.0067(6) 0.0010(6) C5 0.0154(7) 0.0142(8) 0.0157(8) -0.0002(6) 0.0066(6) 0.0006(6) C6 0.0163(7) 0.0136(8) 0.0166(8) 0.0001(6) 0.0067(6) 0.0008(6) C7 0.0152(7) 0.0123(8) 0.0180(8) -0.0004(6) 0.0077(6) 0.0012(6) C8 0.0176(7) 0.0131(8) 0.0179(8) -0.0004(6) 0.0078(6) 0.0017(6) C9 0.0175(7) 0.0153(8) 0.0169(8) 0.0006(6) 0.0064(6) 0.0023(6) C10 0.0234(8) 0.0161(8) 0.0254(9) -0.0007(7) 0.0127(7) 0.0034(6) C11 0.0273(9) 0.0192(9) 0.0313(10) -0.0013(8) 0.0142(8) 0.0053(7) C12 0.0138(7) 0.0134(8) 0.0171(8) 0.0009(6) 0.0061(6) 0.0001(6) C13 0.0141(7) 0.0132(7) 0.0142(7) 0.0000(6) 0.0056(6) 0.0009(6) C14 0.0145(7) 0.0127(8) 0.0149(7) -0.0004(6) 0.0056(6) 0.0007(6) C15 0.0142(7) 0.0139(8) 0.0172(8) 0.0001(6) 0.0065(6) -0.0002(6) C16 0.0134(7) 0.0144(8) 0.0126(7) 0.0015(6) 0.0055(6) -0.0001(6) _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 Br1 C1 1.8728(16) . ? Br2 C12 1.8740(16) . ? S1 C13 1.7217(16) . ? S1 C12 1.7373(15) . ? S2 C16 1.7199(15) . ? S2 C1 1.7332(17) . ? N C14 1.406(2) . ? N C4 1.4092(19) . ? N C3 1.4139(19) . ? O C4 1.2100(19) . ? C1 C2 1.367(2) . ? C2 C3 1.422(2) . ? C2 H2 0.9500 . ? C3 C16 1.388(2) . ? C4 C5 1.505(2) . ? C5 C6 1.531(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.523(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.525(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.525(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.535(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.524(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C15 1.361(2) . ? C13 C14 1.385(2) . ? C13 C16 1.422(2) . ? C14 C15 1.420(2) . ? C15 H15 0.9500 . ? 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 C13 S1 C12 89.53(7) . . ? C16 S2 C1 89.81(8) . . ? C14 N C4 123.21(13) . . ? C14 N C3 106.41(12) . . ? C4 N C3 130.36(13) . . ? C2 C1 S2 115.14(12) . . ? C2 C1 Br1 126.69(13) . . ? S2 C1 Br1 118.16(9) . . ? C1 C2 C3 109.20(14) . . ? C1 C2 H2 125.4 . . ? C3 C2 H2 125.4 . . ? C16 C3 N 108.75(13) . . ? C16 C3 C2 114.05(13) . . ? N C3 C2 137.15(14) . . ? O C4 N 118.98(14) . . ? O C4 C5 123.88(14) . . ? N C4 C5 117.13(13) . . ? C4 C5 C6 112.08(13) . . ? C4 C5 H5A 109.2 . . ? C6 C5 H5A 109.2 . . ? C4 C5 H5B 109.2 . . ? C6 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? C7 C6 C5 112.65(13) . . ? C7 C6 H6A 109.1 . . ? C5 C6 H6A 109.1 . . ? C7 C6 H6B 109.1 . . ? C5 C6 H6B 109.1 . . ? H6A C6 H6B 107.8 . . ? C6 C7 C8 112.48(13) . . ? C6 C7 H7A 109.1 . . ? C8 C7 H7A 109.1 . . ? C6 C7 H7B 109.1 . . ? C8 C7 H7B 109.1 . . ? H7A C7 H7B 107.8 . . ? C9 C8 C7 113.53(13) . . ? C9 C8 H8A 108.9 . . ? C7 C8 H8A 108.9 . . ? C9 C8 H8B 108.9 . . ? C7 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? C8 C9 C10 113.10(13) . . ? C8 C9 H9A 109.0 . . ? C10 C9 H9A 109.0 . . ? C8 C9 H9B 109.0 . . ? C10 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C11 C10 C9 113.40(14) . . ? C11 C10 H10A 108.9 . . ? C9 C10 H10A 108.9 . . ? C11 C10 H10B 108.9 . . ? C9 C10 H10B 108.9 . . ? H10A C10 H10B 107.7 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C15 C12 S1 115.30(12) . . ? C15 C12 Br2 124.66(12) . . ? S1 C12 Br2 120.04(9) . . ? C14 C13 C16 107.04(14) . . ? C14 C13 S1 111.75(12) . . ? C16 C13 S1 141.01(12) . . ? C13 C14 N 109.76(13) . . ? C13 C14 C15 114.30(14) . . ? N C14 C15 135.80(14) . . ? C12 C15 C14 109.12(13) . . ? C12 C15 H15 125.4 . . ? C14 C15 H15 125.4 . . ? C3 C16 C13 108.04(13) . . ? C3 C16 S2 111.80(12) . . ? C13 C16 S2 140.10(13) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.59 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.333 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.058