#============================================================================== data_global #============================================================================== _publ_contact_author 'Pavel K. Mykhailiuk and Edward A. Anderson' _publ_contact_author_email ; pavel.mykhailiuk@gmail.com edward.anderson@chem.ox.ac.uk ; loop_ _publ_author_name _publ_author_address 'Pickford, Helena D.' ; Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA. UK. ; 'Ripenko, Vasyl' ; Enamine Ltd, Chervonotkatska 78, 02094, Kyiv, Ukraine and Chemistry Department, Taras Shevchenko National University of Kyiv, Volodymyrska 64, 01601 Kyiv, Ukraine. ; 'Holovchuk, Serhii' ; Enamine Ltd, Chervonotkatska 78, 02094, Kyiv, Ukraine. ; 'McNamee, Ryan E.' ; Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA. UK. ; 'Thompson, Amber L.' ; Chemical Crystallography Department, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA. UK. ; 'Smith, Russell C.' ; Abbvie Drug Discovery Science & Technology (DDST), 1 North Waukegan Road, North Chicago, IL 60064, USA. ; 'Mykhailiuk, Pavel K.' ; Enamine Ltd, Chervonotkatska 78, 02094, Kyiv, Ukraine. ; 'Anderson, Edward A.' ; Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA. UK. ; _publ_requested_journal 'Angewandte Chemie International Edition' _journal_volume '?' _journal_page_first '?' _journal_page_last '?' _journal_year '2022' _ccdc_journal_depnumber '?' _publ_section_title ; Rapid and Scalable Halosulfonylation of Strain-Release Reagents ; _publ_section_abstract ; Sulfonylated aromatics are commonplace motifs in drugs and agrochemicals. However, methods for the direct synthesis of sulfonylated non-classical arene bioisosteres, which could improve the physicochemical properties of drug / agrochemical candidates, are limited. Here we report a solution to this challenge: a one-pot halosulfonylation of [1.1.1]propellane, [3.1.1]propellane and bicy-clo[1.1.0]butanes that proceeds under practical, scalable and mild conditions. The sulfonyl halides used in this chemistry feature aryl, heteroaryl and alkyl substituents, and are conveniently generated in situ from readily available sulfinate salts and halogen atom sources. This methodology enables the synthe-sis of an array of pharmaceutically-relevant sulfonyl BCP, BCHep and cyclobutyl halides, on milligram to decagram scales. ; #============================================================================== data_3aa-Br #============================================================================== _audit_creation_date "2022-09-06" _audit_creation_method 'CRYSTALS_ver_14.61_build_7986 ' _oxford_structure_analysis_title '7699/020eaa22' _chemical_name_systematic . _chemical_melting_point 'not measured' _cell_length_a 5.4252(1) _cell_length_b 8.3851(2) _cell_length_c 17.2856(4) _cell_angle_alpha 84.376(2) _cell_angle_beta 87.728(2) _cell_angle_gamma 87.057(2) _cell_volume 781.05(3) _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' '-x,-y,-z' 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 0.0181 0.0091 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 0.0492 0.0322 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' Br -0.6763 1.2805 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' N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.3331 0.5567 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' _cell_formula_units_Z 2 # Given Formula = C12 H17 Br1 N4 O3 S1 # Dc = 1.60 Fooo = 384.00 Mu = 49.84 M = 377.26 # Found Formula = C12 H17 Br1 N4 O3 S1 # Dc = 1.60 FOOO = 384.00 Mu = 49.84 M = 377.26 _chemical_formula_sum 'C12 H17 Br N4 O3 S' _chemical_formula_moiety 'C12 H17 Br N4 O3 S' _chemical_compound_source . _chemical_formula_weight 377.26 _cell_measurement_reflns_used 9028 _cell_measurement_theta_min 5.08 _cell_measurement_theta_max 76.23 _cell_measurement_temperature 150 _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_min 0.04 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_max 0.21 _exptl_crystal_density_diffrn 1.604 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 4.984 # Sheldrick geometric approximatio 0.39 0.82 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro (Rigaku Oxford Diffraction, 2017) ; _exptl_absorpt_correction_T_min 0.49 _exptl_absorpt_correction_T_max 0.82 _diffrn_measurement_device_type 'Oxford Diffraction SuperNova' _diffrn_measurement_device 'Area' _diffrn_radiation_monochromator 'focussing mirrors' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SuperNova, (Oxford Diffraction, 2010)' _computing_cell_refinement ; CrysAlisPro (Rigaku Oxford Diffraction, 2017) ; _computing_data_reduction ; CrysAlisPro (Rigaku Oxford Diffraction, 2017) ; _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _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 12809 _diffrn_reflns_av_unetI/netI 0.040 _reflns_number_total 3224 _diffrn_reflns_av_R_equivalents 0.034 # Number of reflections with Friedels Law is 3224 # Theoretical number of reflections is about 6556 _diffrn_reflns_theta_min 5.145 _diffrn_reflns_theta_max 76.390 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 73.335 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _reflns_limit_h_min -6 _reflns_limit_h_max 6 _reflns_limit_k_min -10 _reflns_limit_k_max 10 _reflns_limit_l_min 0 _reflns_limit_l_max 21 _oxford_diffrn_Wilson_B_factor 2.03 _oxford_diffrn_Wilson_scale 0.02 _atom_sites_solution_primary other #heavy,direct,difmap,geom,iterative # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.39 _refine_diff_density_max 0.42 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # Explicitly named reflections are ALWAYS excluded from R&wR # The values actually used during refinement # These are labelled "all" for compatibility with PLATON _oxford_refine_reflns_threshold_expression I>-3.0\s(I) _refine_ls_number_restraints 0 _refine_ls_number_parameters 190 _refine_ls_number_reflns 3224 _refine_ls_R_factor_ref 0.0275 _refine_ls_wR_factor_ref 0.0683 _refine_ls_goodness_of_fit_ref 1.0028 _refine_ls_shift/su_max 0.0048359 _refine_ls_shift/su_mean 0.0000890 # Computed with I/sigma = -10 _reflns_number_all 3224 _refine_ls_R_factor_all 0.0275 _refine_ls_wR_factor_all 0.0683 # Computed with I/sigma = +2 a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3003 _refine_ls_R_factor_gt 0.0256 _refine_ls_wR_factor_gt 0.0664 _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr #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^) + ( 0.04P)^2^ + 0.32P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Oxford Diffraction, (2010). Supernova User Manual. Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790. Rigaku Oxford Diffraction (2017). CrysAlisPro. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached 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 Br1 Br 0.19418(3) 0.25539(3) 1.058523(10) 0.0316 1.0000 Uani . . . . . . C1 C 0.3529(3) 0.2615(2) 0.95650(9) 0.0209 1.0000 Uani . . . . . . C2 C 0.3424(3) 0.4045(2) 0.89269(10) 0.0221 1.0000 Uani . . . . . . C3 C 0.5053(3) 0.26490(19) 0.86138(9) 0.0169 1.0000 Uani . . . . . . C4 C 0.4680(3) 0.34212(19) 0.70142(9) 0.0175 1.0000 Uani . . . . . . C5 C 0.2175(3) 0.3612(2) 0.61295(10) 0.0235 1.0000 Uani . . . . . . C6 C 0.1551(3) 0.66046(19) 0.59608(9) 0.0192 1.0000 Uani . . . . . . C7 C 0.0515(3) 0.74872(19) 0.72860(9) 0.0193 1.0000 Uani . . . . . . C8 C 0.2534(3) 0.8240(2) 0.76915(10) 0.0240 1.0000 Uani . . . . . . C9 C -0.0126(3) 0.9266(2) 0.60560(10) 0.0221 1.0000 Uani . . . . . . C10 C -0.2828(3) 0.9228(2) 0.58713(11) 0.0302 1.0000 Uani . . . . . . C12 C 0.6332(3) 0.2402(2) 0.94096(10) 0.0228 1.0000 Uani . . . . . . C22 C 0.3092(3) 0.1457(2) 0.89449(9) 0.0212 1.0000 Uani . . . . . . N1 N 0.3468(3) 0.25107(17) 0.65592(9) 0.0235 1.0000 Uani . . . . . . N2 N 0.4210(3) 0.49851(16) 0.69118(8) 0.0197 1.0000 Uani . . . . . . N3 N 0.2570(3) 0.50877(16) 0.63359(8) 0.0195 1.0000 Uani . . . . . . N4 N 0.0829(3) 0.77113(16) 0.64319(8) 0.0181 1.0000 Uani . . . . . . S1 S 0.67670(7) 0.26320(4) 0.77266(2) 0.0167 1.0000 Uani . . . . . . O1 O 0.8666(2) 0.37592(15) 0.77451(7) 0.0253 1.0000 Uani . . . . . . O2 O 0.7420(2) 0.09967(15) 0.76049(7) 0.0255 1.0000 Uani . . . . . . O3 O 0.1457(3) 0.67117(15) 0.52548(7) 0.0278 1.0000 Uani . . . . . . H21 H 0.4250 0.5005 0.9037 0.0268 1.0000 Uiso R . . . . . H22 H 0.1894 0.4290 0.8684 0.0270 1.0000 Uiso R . . . . . H51 H 0.1147 0.3430 0.5725 0.0284 1.0000 Uiso R . . . . . H71 H -0.1050 0.8020 0.7419 0.0229 1.0000 Uiso R . . . . . H72 H 0.0439 0.6366 0.7450 0.0228 1.0000 Uiso R . . . . . H81 H 0.2128 0.8180 0.8241 0.0358 1.0000 Uiso R . . . . . H82 H 0.2646 0.9345 0.7497 0.0356 1.0000 Uiso R . . . . . H83 H 0.4080 0.7665 0.7592 0.0363 1.0000 Uiso R . . . . . H91 H 0.0093 1.0061 0.6410 0.0264 1.0000 Uiso R . . . . . H92 H 0.0853 0.9512 0.5584 0.0264 1.0000 Uiso R . . . . . H101 H -0.3471 1.0252 0.5655 0.0451 1.0000 Uiso R . . . . . H102 H -0.3776 0.8933 0.6337 0.0446 1.0000 Uiso R . . . . . H103 H -0.3053 0.8451 0.5508 0.0453 1.0000 Uiso R . . . . . H121 H 0.7320 0.3260 0.9533 0.0281 1.0000 Uiso R . . . . . H122 H 0.7094 0.1376 0.9558 0.0277 1.0000 Uiso R . . . . . H221 H 0.3690 0.0353 0.9045 0.0252 1.0000 Uiso R . . . . . H222 H 0.1510 0.1569 0.8717 0.0246 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 Br1 0.02716(12) 0.04994(14) 0.01807(11) -0.00558(8) 0.00099(7) -0.00303(8) C1 0.0166(7) 0.0296(9) 0.0166(7) -0.0028(6) -0.0012(6) -0.0004(6) C2 0.0226(8) 0.0231(8) 0.0207(8) -0.0039(6) -0.0023(6) 0.0025(6) C3 0.0153(7) 0.0196(7) 0.0157(7) -0.0009(6) -0.0028(6) 0.0001(6) C4 0.0185(7) 0.0190(7) 0.0147(7) -0.0009(6) -0.0029(6) 0.0007(6) C5 0.0296(9) 0.0206(8) 0.0216(8) -0.0059(6) -0.0098(7) 0.0004(6) C6 0.0209(7) 0.0185(7) 0.0182(7) -0.0001(6) -0.0067(6) 0.0003(6) C7 0.0219(8) 0.0202(7) 0.0153(7) 0.0005(6) 0.0003(6) -0.0014(6) C8 0.0281(9) 0.0264(8) 0.0182(8) -0.0044(6) -0.0019(6) -0.0043(7) C9 0.0278(8) 0.0172(7) 0.0202(8) 0.0022(6) -0.0025(6) 0.0018(6) C10 0.0254(9) 0.0361(10) 0.0272(9) 0.0026(7) -0.0022(7) 0.0085(7) C12 0.0181(8) 0.0320(9) 0.0181(7) -0.0003(6) -0.0054(6) -0.0003(6) C22 0.0209(8) 0.0241(8) 0.0187(7) -0.0014(6) -0.0011(6) -0.0047(6) N1 0.0273(7) 0.0197(7) 0.0247(7) -0.0054(5) -0.0089(6) 0.0003(5) N2 0.0226(7) 0.0188(6) 0.0184(6) -0.0022(5) -0.0079(5) 0.0005(5) N3 0.0237(7) 0.0189(7) 0.0166(6) -0.0030(5) -0.0079(5) 0.0009(5) N4 0.0211(7) 0.0166(6) 0.0161(6) 0.0011(5) -0.0041(5) -0.0005(5) S1 0.01465(17) 0.01832(18) 0.01675(18) 0.00022(13) -0.00258(13) 0.00075(13) O1 0.0189(6) 0.0303(6) 0.0266(6) 0.0032(5) -0.0052(5) -0.0066(5) O2 0.0276(6) 0.0223(6) 0.0256(6) -0.0020(5) -0.0016(5) 0.0072(5) O3 0.0397(7) 0.0268(6) 0.0169(6) -0.0021(5) -0.0096(5) 0.0037(5) _refine_ls_extinction_method 'None' _oxford_refine_ls_scale 6.73(13) 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 Br1 . C1 . 1.9290(16) yes C1 . C2 . 1.548(2) yes C1 . C3 . 1.809(2) yes C1 . C12 . 1.538(2) yes C1 . C22 . 1.548(2) yes C2 . C3 . 1.557(2) yes C2 . H21 . 0.979 no C2 . H22 . 0.949 no C3 . C12 . 1.556(2) yes C3 . C22 . 1.551(2) yes C3 . S1 . 1.7626(16) yes C4 . N1 . 1.358(2) yes C4 . N2 . 1.319(2) yes C4 . S1 . 1.7637(16) yes C5 . N1 . 1.318(2) yes C5 . N3 . 1.351(2) yes C5 . H51 . 0.940 no C6 . N3 . 1.462(2) yes C6 . N4 . 1.328(2) yes C6 . O3 . 1.218(2) yes C7 . C8 . 1.519(2) yes C7 . N4 . 1.474(2) yes C7 . H71 . 0.969 no C7 . H72 . 0.958 no C8 . H81 . 0.964 no C8 . H82 . 0.958 no C8 . H83 . 0.964 no C9 . C10 . 1.515(3) yes C9 . N4 . 1.477(2) yes C9 . H91 . 0.962 no C9 . H92 . 0.966 no C10 . H101 . 0.956 no C10 . H102 . 0.957 no C10 . H103 . 0.964 no C12 . H121 . 0.964 no C12 . H122 . 0.951 no C22 . H221 . 0.966 no C22 . H222 . 0.955 no N2 . N3 . 1.3548(19) yes S1 . O1 . 1.4370(12) yes S1 . O2 . 1.4320(13) 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 Br1 . C1 . C2 . 126.22(12) yes Br1 . C1 . C3 . 179.11(11) yes C2 . C1 . C3 . 54.60(9) yes Br1 . C1 . C12 . 124.59(12) yes C2 . C1 . C12 . 89.75(12) yes C3 . C1 . C12 . 54.69(9) yes Br1 . C1 . C22 . 125.53(12) yes C2 . C1 . C22 . 89.71(12) yes C3 . C1 . C22 . 54.37(9) yes C12 . C1 . C22 . 89.75(12) yes C1 . C2 . C3 . 71.29(11) yes C1 . C2 . H21 . 116.3 no C3 . C2 . H21 . 117.6 no C1 . C2 . H22 . 117.2 no C3 . C2 . H22 . 116.0 no H21 . C2 . H22 . 112.7 no C2 . C3 . C1 . 54.12(9) yes C2 . C3 . C12 . 88.74(12) yes C1 . C3 . C12 . 53.75(9) yes C2 . C3 . C22 . 89.25(12) yes C1 . C3 . C22 . 54.20(9) yes C12 . C3 . C22 . 88.96(12) yes C2 . C3 . S1 . 128.69(12) yes C1 . C3 . S1 . 175.23(11) yes C12 . C3 . S1 . 121.53(11) yes C22 . C3 . S1 . 127.49(12) yes N1 . C4 . N2 . 116.69(14) yes N1 . C4 . S1 . 123.97(12) yes N2 . C4 . S1 . 119.34(12) yes N1 . C5 . N3 . 110.33(15) yes N1 . C5 . H51 . 126.3 no N3 . C5 . H51 . 123.4 no N3 . C6 . N4 . 116.02(14) yes N3 . C6 . O3 . 116.62(15) yes N4 . C6 . O3 . 127.36(15) yes C8 . C7 . N4 . 112.35(13) yes C8 . C7 . H71 . 108.1 no N4 . C7 . H71 . 106.9 no C8 . C7 . H72 . 111.4 no N4 . C7 . H72 . 109.2 no H71 . C7 . H72 . 108.8 no C7 . C8 . H81 . 108.9 no C7 . C8 . H82 . 110.1 no H81 . C8 . H82 . 108.7 no C7 . C8 . H83 . 108.5 no H81 . C8 . H83 . 110.9 no H82 . C8 . H83 . 109.7 no C10 . C9 . N4 . 111.89(14) yes C10 . C9 . H91 . 110.1 no N4 . C9 . H91 . 107.2 no C10 . C9 . H92 . 110.2 no N4 . C9 . H92 . 107.9 no H91 . C9 . H92 . 109.5 no C9 . C10 . H101 . 111.9 no C9 . C10 . H102 . 109.7 no H101 . C10 . H102 . 107.8 no C9 . C10 . H103 . 110.4 no H101 . C10 . H103 . 108.7 no H102 . C10 . H103 . 108.3 no C1 . C12 . C3 . 71.57(11) yes C1 . C12 . H121 . 116.6 no C3 . C12 . H121 . 116.3 no C1 . C12 . H122 . 117.4 no C3 . C12 . H122 . 117.9 no H121 . C12 . H122 . 111.9 no C1 . C22 . C3 . 71.43(11) yes C1 . C22 . H221 . 117.8 no C3 . C22 . H221 . 115.4 no C1 . C22 . H222 . 115.8 no C3 . C22 . H222 . 117.0 no H221 . C22 . H222 . 113.3 no C4 . N1 . C5 . 101.69(14) yes C4 . N2 . N3 . 101.01(13) yes C6 . N3 . N2 . 123.77(13) yes C6 . N3 . C5 . 125.80(14) yes N2 . N3 . C5 . 110.27(13) yes C9 . N4 . C7 . 115.81(13) yes C9 . N4 . C6 . 116.36(13) yes C7 . N4 . C6 . 127.11(13) yes C4 . S1 . C3 . 104.61(7) yes C4 . S1 . O1 . 107.56(7) yes C3 . S1 . O1 . 106.90(8) yes C4 . S1 . O2 . 108.79(8) yes C3 . S1 . O2 . 108.07(7) yes O1 . S1 . O2 . 119.89(8) yes loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C2 . H22 . O1 1_455 152 0.95 2.52 3.387(2) yes C5 . H51 . O3 2_566 174 0.94 2.26 3.200(2) yes C7 . H72 . O1 1_455 159 0.96 2.43 3.344(2) yes _iucr_refine_instructions_details ; # # Punched on 06/09/22 at 14:41:09 # #LIST 12 BLOCK SCALE X'S U'S RIDE C ( 2,X'S) H ( 21,X'S) H ( 22,X'S) RIDE C ( 5,X'S) H ( 51,X'S) RIDE C ( 7,X'S) H ( 71,X'S) H ( 72,X'S) RIDE C ( 8,X'S) H ( 81,X'S) H ( 82,X'S) H ( 83,X'S) RIDE C ( 9,X'S) H ( 91,X'S) H ( 92,X'S) RIDE C ( 10,X'S) H ( 101,X'S) H ( 102,X'S) H ( 103,X'S) RIDE C ( 12,X'S) H ( 121,X'S) H ( 122,X'S) RIDE C ( 22,X'S) H ( 221,X'S) H ( 222,X'S) END # # Punched on 06/09/22 at 14:41:09 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; _refine_special_details ; ? Reflections are selected by the following conditions :- Minimum value of SQRTW is 0.00 Minimum value of RATIO is -3.00 ; #============================================================================== data_5a-I #============================================================================== _audit_creation_date "2022-09-07" _audit_creation_method 'CRYSTALS_ver_14.61_build_7986 ' _oxford_structure_analysis_title '7701/010eaa21' _chemical_name_systematic . _chemical_melting_point 'not measured' _cell_length_a 10.2852(2) _cell_length_b 11.9116(2) _cell_length_c 23.6450(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2896.82(10) _symmetry_cell_setting 'orthorhombic' _symmetry_space_group_name_H-M 'P b c a ' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' '-x,-y,-z' '-x+1/2,y+1/2,z' 'x+1/2,-y+1/2,-z' '-x+1/2,-y,z+1/2' 'x+1/2,y,-z+1/2' '-x,y+1/2,-z+1/2' 'x,-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 0.0181 0.0091 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 0.0492 0.0322 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' I -0.3257 6.8362 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776 4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.3331 0.5567 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' _cell_formula_units_Z 8 # Given Formula = C14 H17 I1 O2 S1 # Dc = 1.73 Fooo = 1488.00 Mu = 186.54 M = 376.26 # Found Formula = C14 H17 I1 O2 S1 # Dc = 1.73 FOOO = 1488.00 Mu = 186.54 M = 376.26 _chemical_formula_sum 'C14 H17 I O2 S' _chemical_formula_moiety 'C14 H17 I O2 S' _chemical_compound_source . _chemical_formula_weight 376.26 _cell_measurement_reflns_used 8761 _cell_measurement_theta_min 5.95 _cell_measurement_theta_max 75.94 _cell_measurement_temperature 150 _exptl_crystal_description 'block' _exptl_crystal_colour 'clear_pale_colourless' _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_max 0.20 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 0 0.04 0 -1 0 0.04 0 0 -1 0.08 0 0 1 0.09 -1 1 1 0.06 1 -1 -1 0.07 -1 1 -1 0.06 1 -1 1 0.08 1 1 1 0.08 -1 -1 -1 0.04 1 1 -1 0.05 -1 -1 1 0.05 _exptl_crystal_density_diffrn 1.725 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 18.654 # Sheldrick geometric approximatio 0.06 0.22 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _oxdiff_exptl_absorpt_empirical_full_min 0.671 _oxdiff_exptl_absorpt_empirical_full_max 1.630 _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _exptl_absorpt_correction_T_min 0.05 _exptl_absorpt_correction_T_max 0.22 _diffrn_measurement_device_type 'Oxford Diffraction SuperNova' _diffrn_measurement_device 'Area' _diffrn_radiation_monochromator 'focussing mirrors' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SuperNova, (Oxford Diffraction, 2010)' _computing_cell_refinement ; CrysAlisPro (Rigaku Oxford Diffraction, 2017) ; _computing_data_reduction ; CrysAlisPro (Rigaku Oxford Diffraction, 2017) ; _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _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 30927 _diffrn_reflns_av_unetI/netI 0.062 _reflns_number_total 3026 _diffrn_reflns_av_R_equivalents 0.056 # Number of reflections with Friedels Law is 3026 # Theoretical number of reflections is about 6064 _diffrn_reflns_theta_min 3.739 _diffrn_reflns_theta_max 76.196 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 76.196 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 29 _reflns_limit_h_min 0 _reflns_limit_h_max 12 _reflns_limit_k_min 0 _reflns_limit_k_max 14 _reflns_limit_l_min 0 _reflns_limit_l_max 29 _oxford_diffrn_Wilson_B_factor 2.93 _oxford_diffrn_Wilson_scale 0.28 _atom_sites_solution_primary other #heavy,direct,difmap,geom,iterative # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -1.83 _refine_diff_density_max 1.36 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # Explicitly named reflections are ALWAYS excluded from R&wR # The values actually used during refinement # These are labelled "all" for compatibility with PLATON _oxford_refine_reflns_threshold_expression I>-3.0\s(I) _refine_ls_number_restraints 0 _refine_ls_number_parameters 163 _refine_ls_number_reflns 3026 _refine_ls_R_factor_ref 0.0454 _refine_ls_wR_factor_ref 0.1066 _refine_ls_goodness_of_fit_ref 0.9917 _refine_ls_shift/su_max 0.0008682 _refine_ls_shift/su_mean 0.0000450 # Computed with I/sigma = -10 _reflns_number_all 3026 _refine_ls_R_factor_all 0.0454 _refine_ls_wR_factor_all 0.1066 # Computed with I/sigma = +2 a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2664 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_gt 0.1014 _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment noref #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^) + ( 0.05P)^2^ + 7.87P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Busing, W.R. & Levy, H.A., (1975). Acta Cryst 10, 180. Oxford Diffraction, (2010). Supernova User Manual. Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790. Rigaku Oxford Diffraction (2017). CrysAlisPro. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached 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 I1 I 1.02444(2) 0.49746(2) 0.389850(14) 0.0470 1.0000 Uani . . . . . . C1 C 0.8438(3) 0.4226(3) 0.41682(14) 0.0280 1.0000 Uani . . . . . . C2 C 0.8658(4) 0.3258(3) 0.45804(16) 0.0363 1.0000 Uani . . . . . . C3 C 0.7362(4) 0.2977(3) 0.48836(15) 0.0368 1.0000 Uani . . . . . . C4 C 0.6139(4) 0.3220(3) 0.45298(14) 0.0294 1.0000 Uani . . . . . . C5 C 0.6416(3) 0.4193(2) 0.41267(12) 0.0220 1.0000 Uani . . . . . . C6 C 0.7495(3) 0.3868(3) 0.36978(13) 0.0249 1.0000 Uani . . . . . . C7 C 0.4236(3) 0.3760(3) 0.34404(13) 0.0238 1.0000 Uani . . . . . . C8 C 0.3214(3) 0.3172(3) 0.36814(14) 0.0295 1.0000 Uani . . . . . . C9 C 0.2591(3) 0.2345(3) 0.33750(16) 0.0312 1.0000 Uani . . . . . . C10 C 0.2996(3) 0.2082(3) 0.28284(14) 0.0289 1.0000 Uani . . . . . . C11 C 0.2325(4) 0.1165(3) 0.25004(18) 0.0408 1.0000 Uani . . . . . . C12 C 0.4032(3) 0.2677(3) 0.25953(14) 0.0301 1.0000 Uani . . . . . . C13 C 0.4653(3) 0.3517(3) 0.28923(14) 0.0291 1.0000 Uani . . . . . . C16 C 0.7395(3) 0.5047(2) 0.43899(14) 0.0243 1.0000 Uani . . . . . . S1 S 0.49852(9) 0.48305(7) 0.38393(3) 0.0235 1.0000 Uani . . . . . . O1 O 0.5409(2) 0.5705(2) 0.34592(11) 0.0322 1.0000 Uani . . . . . . O2 O 0.4142(3) 0.5128(2) 0.43003(12) 0.0364 1.0000 Uani . . . . . . H21 H 0.9297 0.3478 0.4861 0.0441 1.0000 Uiso . . . . . . H22 H 0.8964 0.2603 0.4377 0.0439 1.0000 Uiso . . . . . . H31 H 0.7302 0.3444 0.5221 0.0437 1.0000 Uiso . . . . . . H32 H 0.7369 0.2190 0.4995 0.0443 1.0000 Uiso . . . . . . H41 H 0.5430 0.3430 0.4781 0.0353 1.0000 Uiso . . . . . . H42 H 0.5891 0.2565 0.4315 0.0353 1.0000 Uiso . . . . . . H61 H 0.7538 0.4351 0.3368 0.0298 1.0000 Uiso . . . . . . H62 H 0.7525 0.3084 0.3583 0.0300 1.0000 Uiso . . . . . . H81 H 0.2951 0.3330 0.4052 0.0353 1.0000 Uiso . . . . . . H91 H 0.1894 0.1964 0.3532 0.0372 1.0000 Uiso . . . . . . H111 H 0.2445 0.1266 0.2104 0.0614 1.0000 Uiso . . . . . . H112 H 0.2685 0.0456 0.2608 0.0612 1.0000 Uiso . . . . . . H113 H 0.1419 0.1163 0.2585 0.0615 1.0000 Uiso . . . . . . H121 H 0.4308 0.2510 0.2229 0.0360 1.0000 Uiso . . . . . . H131 H 0.5342 0.3917 0.2728 0.0352 1.0000 Uiso . . . . . . H161 H 0.7338 0.5149 0.4801 0.0288 1.0000 Uiso . . . . . . H162 H 0.7388 0.5779 0.4200 0.0287 1.0000 Uiso . . . . . . 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 I1 0.02106(18) 0.0526(2) 0.0673(2) -0.01352(12) 0.00452(11) -0.00105(9) C1 0.0232(15) 0.0287(15) 0.0320(16) -0.0052(13) -0.0034(13) 0.0044(12) C2 0.044(2) 0.0297(16) 0.0354(18) -0.0066(14) -0.0166(16) 0.0129(15) C3 0.063(3) 0.0237(16) 0.0233(14) -0.0005(12) -0.0073(16) 0.0072(16) C4 0.0415(19) 0.0211(14) 0.0256(15) 0.0009(12) 0.0037(14) -0.0021(13) C5 0.0243(15) 0.0220(13) 0.0197(13) -0.0014(11) 0.0016(11) 0.0006(11) C6 0.0254(15) 0.0266(15) 0.0228(13) -0.0019(11) 0.0000(12) 0.0050(12) C7 0.0193(14) 0.0289(15) 0.0234(14) -0.0032(12) 0.0002(11) 0.0034(12) C8 0.0247(16) 0.0380(17) 0.0258(15) -0.0011(13) 0.0066(13) -0.0008(13) C9 0.0251(16) 0.0367(17) 0.0319(16) -0.0025(14) 0.0057(13) -0.0024(13) C10 0.0253(15) 0.0321(16) 0.0293(16) -0.0043(13) -0.0017(13) 0.0019(13) C11 0.035(2) 0.042(2) 0.045(2) -0.0159(17) 0.0022(16) -0.0045(16) C12 0.0276(16) 0.0404(17) 0.0223(15) -0.0045(13) 0.0024(13) 0.0031(14) C13 0.0238(16) 0.0392(17) 0.0242(15) -0.0002(13) 0.0033(12) -0.0014(13) C16 0.0262(16) 0.0195(13) 0.0271(15) -0.0012(10) -0.0012(13) 0.0004(11) S1 0.0220(3) 0.0244(3) 0.0240(4) -0.0023(3) 0.0006(3) 0.0014(3) O1 0.0333(12) 0.0268(11) 0.0367(13) 0.0059(10) -0.0044(10) 0.0021(10) O2 0.0303(13) 0.0430(14) 0.0359(13) -0.0117(11) 0.0051(11) 0.0048(11) _refine_ls_extinction_method 'None' _oxford_refine_ls_scale 2.016(17) 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 I1 . C1 . 2.157(4) yes C1 . C2 . 1.527(5) yes C1 . C6 . 1.536(4) yes C1 . C16 . 1.543(4) yes C2 . C3 . 1.550(6) yes C2 . H21 . 0.970 no C2 . H22 . 0.970 no C3 . C4 . 1.538(5) yes C3 . H31 . 0.974 no C3 . H32 . 0.974 no C4 . C5 . 1.527(4) yes C4 . H41 . 0.973 no C4 . H42 . 0.966 no C5 . C6 . 1.553(4) yes C5 . C16 . 1.561(4) yes C5 . S1 . 1.789(3) yes C6 . H61 . 0.970 no C6 . H62 . 0.973 no C7 . C8 . 1.386(5) yes C7 . C13 . 1.396(4) yes C7 . S1 . 1.763(3) yes C8 . C9 . 1.380(5) yes C8 . H81 . 0.935 no C9 . C10 . 1.394(5) yes C9 . H91 . 0.927 no C10 . C11 . 1.507(5) yes C10 . C12 . 1.393(5) yes C11 . H111 . 0.953 no C11 . H112 . 0.957 no C11 . H113 . 0.954 no C12 . C13 . 1.380(5) yes C12 . H121 . 0.932 no C13 . H131 . 0.937 no C16 . H161 . 0.982 no C16 . H162 . 0.980 no S1 . O1 . 1.443(3) yes S1 . O2 . 1.437(3) 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 I1 . C1 . C2 . 111.9(2) yes I1 . C1 . C6 . 116.4(2) yes C2 . C1 . C6 . 110.2(3) yes I1 . C1 . C16 . 115.9(2) yes C2 . C1 . C16 . 111.4(3) yes C6 . C1 . C16 . 89.1(2) yes C1 . C2 . C3 . 109.3(3) yes C1 . C2 . H21 . 109.5 no C3 . C2 . H21 . 109.0 no C1 . C2 . H22 . 109.8 no C3 . C2 . H22 . 109.6 no H21 . C2 . H22 . 109.7 no C2 . C3 . C4 . 114.3(3) yes C2 . C3 . H31 . 108.1 no C4 . C3 . H31 . 106.6 no C2 . C3 . H32 . 109.1 no C4 . C3 . H32 . 109.5 no H31 . C3 . H32 . 109.1 no C3 . C4 . C5 . 109.3(3) yes C3 . C4 . H41 . 109.2 no C5 . C4 . H41 . 109.0 no C3 . C4 . H42 . 110.5 no C5 . C4 . H42 . 109.5 no H41 . C4 . H42 . 109.3 no C4 . C5 . C6 . 110.5(3) yes C4 . C5 . C16 . 111.5(3) yes C6 . C5 . C16 . 87.8(2) yes C4 . C5 . S1 . 113.9(2) yes C6 . C5 . S1 . 116.5(2) yes C16 . C5 . S1 . 113.9(2) yes C1 . C6 . C5 . 84.8(2) yes C1 . C6 . H61 . 112.8 no C5 . C6 . H61 . 114.1 no C1 . C6 . H62 . 116.7 no C5 . C6 . H62 . 116.4 no H61 . C6 . H62 . 110.1 no C8 . C7 . C13 . 120.7(3) yes C8 . C7 . S1 . 118.5(2) yes C13 . C7 . S1 . 120.8(3) yes C7 . C8 . C9 . 119.8(3) yes C7 . C8 . H81 . 120.1 no C9 . C8 . H81 . 120.1 no C8 . C9 . C10 . 120.6(3) yes C8 . C9 . H91 . 119.9 no C10 . C9 . H91 . 119.5 no C9 . C10 . C11 . 120.2(3) yes C9 . C10 . C12 . 118.8(3) yes C11 . C10 . C12 . 121.0(3) yes C10 . C11 . H111 . 110.9 no C10 . C11 . H112 . 109.0 no H111 . C11 . H112 . 108.8 no C10 . C11 . H113 . 110.0 no H111 . C11 . H113 . 109.5 no H112 . C11 . H113 . 108.6 no C10 . C12 . C13 . 121.4(3) yes C10 . C12 . H121 . 119.5 no C13 . C12 . H121 . 119.1 no C7 . C13 . C12 . 118.7(3) yes C7 . C13 . H131 . 120.8 no C12 . C13 . H131 . 120.5 no C1 . C16 . C5 . 84.3(2) yes C1 . C16 . H161 . 117.2 no C5 . C16 . H161 . 115.9 no C1 . C16 . H162 . 114.4 no C5 . C16 . H162 . 113.1 no H161 . C16 . H162 . 110.1 no C5 . S1 . C7 . 104.84(14) yes C5 . S1 . O1 . 107.12(15) yes C7 . S1 . O1 . 108.71(15) yes C5 . S1 . O2 . 108.20(15) yes C7 . S1 . O2 . 108.66(16) yes O1 . S1 . O2 . 118.48(16) yes loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C3 . H31 . O2 2_666 142 0.97 2.53 3.349(5) yes _iucr_refine_instructions_details ; # # Punched on 07/09/22 at 18:10:39 # #LIST 12 BLOCK SCALE X'S U'S END # # Punched on 07/09/22 at 18:10:39 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; _refine_special_details ; ? Reflections are selected by the following conditions :- Minimum value of SQRTW is 0.00 Minimum value of RATIO is -3.00 ; #============================================================================== data_10d-I #============================================================================== _audit_creation_date "2022-09-08" _audit_creation_method 'CRYSTALS_ver_14.61_build_7986 ' _oxford_structure_analysis_title '7698' _chemical_name_systematic . _chemical_melting_point 'not measured' _cell_length_a 9.6739(2) _cell_length_b 13.3506(4) _cell_length_c 15.7257(4) _cell_angle_alpha 90 _cell_angle_beta 92.361(2) _cell_angle_gamma 90 _cell_volume 2029.29(9) _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,-z' 'x,-y+1/2,z+1/2' '-x,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 0.0181 0.0091 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' N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' I -0.3257 6.8362 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776 4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0492 0.0322 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 0.3331 0.5567 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' _cell_formula_units_Z 4 # Given Formula = C19 H28 I1 N1 O3 S1 # Dc = 1.56 Fooo = 968.00 Mu = 134.99 M = 477.41 # Found Formula = C19 H28 I1 N1 O3 S1 # Dc = 1.56 FOOO = 968.00 Mu = 134.99 M = 477.41 _chemical_formula_sum 'C19 H28 I N O3 S' _chemical_formula_moiety 'C19 H28 I N O3 S' _chemical_compound_source . _chemical_formula_weight 477.41 _cell_measurement_reflns_used 8855 _cell_measurement_theta_min 4.30 _cell_measurement_theta_max 76.39 _cell_measurement_temperature 150 _exptl_crystal_description 'plate' _exptl_crystal_colour 'clear_pale_colourless' _exptl_crystal_size_min 0.03 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_max 0.30 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1 1 -1 0.09 2 -1 -1 0.04 -1 0 1 0.07 0 1 1 0.02 0 -1 -1 0.01 0 0 1 0.12 0 0 -1 0.10 1 2 1 0.03 -2 -1 5 0.10 -3 2 -1 0.08 _exptl_crystal_density_diffrn 1.563 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 13.499 # Sheldrick geometric approximatio 0.17 0.67 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.57a (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _oxdiff_exptl_absorpt_empirical_full_min 0.700 _oxdiff_exptl_absorpt_empirical_full_max 1.517 _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _exptl_absorpt_correction_T_min 0.12 _exptl_absorpt_correction_T_max 0.67 _diffrn_measurement_device_type 'Oxford Diffraction SuperNova' _diffrn_measurement_device 'Area' _diffrn_radiation_monochromator 'focussing mirrors' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SuperNova, (Oxford Diffraction, 2010)' _computing_cell_refinement ; CrysAlisPro (Rigaku Oxford Diffraction, 2017) ; _computing_data_reduction ; CrysAlisPro (Rigaku Oxford Diffraction, 2017) ; _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _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 18556 _diffrn_reflns_av_unetI/netI 0.099 _reflns_number_total 4204 _diffrn_reflns_av_R_equivalents 0.067 # Number of reflections with Friedels Law is 4204 # Theoretical number of reflections is about 8499 _diffrn_reflns_theta_min 4.346 _diffrn_reflns_theta_max 76.231 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 74.706 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _reflns_limit_h_min -12 _reflns_limit_h_max 12 _reflns_limit_k_min 0 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 19 _oxford_diffrn_Wilson_B_factor 2.36 _oxford_diffrn_Wilson_scale 0.08 _atom_sites_solution_primary other #heavy,direct,difmap,geom,iterative # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -1.01 _refine_diff_density_max 0.91 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # Explicitly named reflections are ALWAYS excluded from R&wR # The values actually used during refinement # These are labelled "all" for compatibility with PLATON _oxford_refine_reflns_threshold_expression I>-3.0\s(I) _refine_ls_number_restraints 0 _refine_ls_number_parameters 226 _refine_ls_number_reflns 4203 _refine_ls_R_factor_ref 0.0474 _refine_ls_wR_factor_ref 0.1095 _refine_ls_goodness_of_fit_ref 1.0286 _refine_ls_shift/su_max 0.0020411 _refine_ls_shift/su_mean 0.0000698 # Computed with I/sigma = -10 _reflns_number_all 4204 _refine_ls_R_factor_all 0.0475 _refine_ls_wR_factor_all 0.1097 # Computed with I/sigma = +2 a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3683 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_gt 0.0992 _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr #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^) + ( 0.05P)^2^ + 2.54P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Busing, W.R. & Levy, H.A., (1975). Acta Cryst 10, 180. Oxford Diffraction, (2010). Supernova User Manual. Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790. Rigaku Oxford Diffraction (2017). CrysAlisPro. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached 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 I1 I 1.03437(2) 0.69747(2) 0.582647(17) 0.0316 1.0000 Uani . . . . . . C1 C 0.3977(5) 0.5138(3) 0.9019(3) 0.0360 1.0000 Uani . . . . . . C2 C 0.4110(4) 0.5562(3) 0.8135(2) 0.0276 1.0000 Uani . . . . . . C3 C 0.4343(4) 0.4935(3) 0.7445(3) 0.0295 1.0000 Uani . . . . . . C4 C 0.4502(4) 0.5312(3) 0.6631(2) 0.0281 1.0000 Uani . . . . . . C5 C 0.4433(4) 0.6342(3) 0.6514(2) 0.0261 1.0000 Uani . . . . . . C6 C 0.6528(4) 0.6972(3) 0.5395(2) 0.0258 1.0000 Uani . . . . . . C7 C 0.7379(4) 0.6005(3) 0.5590(2) 0.0259 1.0000 Uani . . . . . . C8 C 0.8291(4) 0.6605(3) 0.6249(2) 0.0275 1.0000 Uani . . . . . . C9 C 0.8459(4) 0.6241(3) 0.7179(2) 0.0267 1.0000 Uani . . . . . . C10 C 0.9335(4) 0.4571(3) 0.6694(2) 0.0277 1.0000 Uani . . . . . . C11 C 0.8404(5) 0.3652(3) 0.6716(3) 0.0351 1.0000 Uani . . . . . . C12 C 1.0863(5) 0.4302(4) 0.6784(3) 0.0410 1.0000 Uani . . . . . . C13 C 0.9149(4) 0.4986(3) 0.8248(2) 0.0314 1.0000 Uani . . . . . . C14 C 0.7782(5) 0.4885(4) 0.8689(3) 0.0388 1.0000 Uani . . . . . . C15 C 1.0176(5) 0.5668(5) 0.8740(3) 0.0436 1.0000 Uani . . . . . . C16 C 0.6732(5) 0.7442(4) 0.4523(3) 0.0354 1.0000 Uani . . . . . . C23 C 0.4001(4) 0.6591(3) 0.7995(2) 0.0294 1.0000 Uani . . . . . . C24 C 0.4161(4) 0.6985(3) 0.7186(3) 0.0287 1.0000 Uani . . . . . . C27 C 0.7294(4) 0.7505(3) 0.6150(3) 0.0292 1.0000 Uani . . . . . . S1 S 0.46816(9) 0.68555(7) 0.54955(6) 0.0253 1.0000 Uani . . . . . . O2 O 0.4098(3) 0.7851(2) 0.5477(2) 0.0360 1.0000 Uani . . . . . . O1 O 0.4185(3) 0.6139(2) 0.48641(18) 0.0338 1.0000 Uani . . . . . . O18 O 0.8131(3) 0.6825(2) 0.77382(19) 0.0362 1.0000 Uani . . . . . . N1 N 0.8950(3) 0.5306(3) 0.73476(19) 0.0264 1.0000 Uani . . . . . . H11 H 0.4003 0.5675 0.9424 0.0540 1.0000 Uiso R . . . . . H13 H 0.4712 0.4673 0.9156 0.0544 1.0000 Uiso R . . . . . H12 H 0.3108 0.4802 0.9054 0.0539 1.0000 Uiso R . . . . . H31 H 0.4395 0.4250 0.7533 0.0346 1.0000 Uiso R . . . . . H41 H 0.4669 0.4885 0.6175 0.0339 1.0000 Uiso R . . . . . H71 H 0.7865 0.5739 0.5117 0.0309 1.0000 Uiso R . . . . . H72 H 0.6841 0.5480 0.5839 0.0306 1.0000 Uiso R . . . . . H101 H 0.9172 0.4881 0.6132 0.0330 1.0000 Uiso R . . . . . H112 H 0.7445 0.3852 0.6653 0.0527 1.0000 Uiso R . . . . . H111 H 0.8553 0.3294 0.7243 0.0532 1.0000 Uiso R . . . . . H113 H 0.8616 0.3211 0.6258 0.0532 1.0000 Uiso R . . . . . H122 H 1.1416 0.4894 0.6759 0.0608 1.0000 Uiso R . . . . . H121 H 1.1052 0.3968 0.7321 0.0609 1.0000 Uiso R . . . . . H123 H 1.1107 0.3853 0.6332 0.0610 1.0000 Uiso R . . . . . H131 H 0.9560 0.4319 0.8242 0.0384 1.0000 Uiso R . . . . . H142 H 0.7185 0.4423 0.8373 0.0580 1.0000 Uiso R . . . . . H141 H 0.7955 0.4630 0.9254 0.0577 1.0000 Uiso R . . . . . H143 H 0.7342 0.5525 0.8717 0.0578 1.0000 Uiso R . . . . . H152 H 1.0992 0.5763 0.8422 0.0648 1.0000 Uiso R . . . . . H151 H 1.0434 0.5372 0.9275 0.0650 1.0000 Uiso R . . . . . H153 H 0.9750 0.6306 0.8835 0.0651 1.0000 Uiso R . . . . . H161 H 0.6294 0.8087 0.4505 0.0527 1.0000 Uiso R . . . . . H163 H 0.7709 0.7523 0.4445 0.0530 1.0000 Uiso R . . . . . H162 H 0.6331 0.7024 0.4084 0.0529 1.0000 Uiso R . . . . . H231 H 0.3816 0.7017 0.8443 0.0353 1.0000 Uiso R . . . . . H241 H 0.4071 0.7662 0.7093 0.0340 1.0000 Uiso R . . . . . H271 H 0.7745 0.8127 0.5992 0.0349 1.0000 Uiso R . . . . . H272 H 0.6738 0.7605 0.6631 0.0346 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 I1 0.02204(15) 0.03806(16) 0.03490(16) 0.00389(10) 0.00431(10) -0.00405(9) C1 0.042(2) 0.039(2) 0.0273(18) 0.0023(16) 0.0008(16) -0.0005(18) C2 0.0207(16) 0.035(2) 0.0270(17) 0.0021(15) 0.0009(13) -0.0025(14) C3 0.0267(18) 0.0296(18) 0.0321(18) 0.0015(15) 0.0013(14) 0.0012(15) C4 0.0224(16) 0.0323(19) 0.0297(17) -0.0044(15) 0.0015(14) -0.0019(14) C5 0.0202(16) 0.0346(19) 0.0235(16) -0.0007(14) -0.0003(13) 0.0015(14) C6 0.0215(16) 0.0291(18) 0.0269(17) 0.0042(14) 0.0006(13) 0.0034(13) C7 0.0230(16) 0.0293(17) 0.0255(16) 0.0035(14) 0.0023(13) 0.0016(14) C8 0.0260(17) 0.0263(17) 0.0304(18) 0.0023(14) 0.0054(14) -0.0001(14) C9 0.0232(16) 0.0309(18) 0.0261(17) -0.0013(14) 0.0019(13) -0.0015(14) C10 0.0285(18) 0.0286(18) 0.0262(17) 0.0006(14) 0.0029(14) 0.0057(14) C11 0.042(2) 0.033(2) 0.0307(19) 0.0009(16) -0.0022(16) 0.0002(17) C12 0.031(2) 0.052(3) 0.040(2) 0.005(2) 0.0076(17) 0.0133(19) C13 0.0296(19) 0.041(2) 0.0237(17) 0.0049(15) -0.0003(14) 0.0044(16) C14 0.038(2) 0.047(2) 0.0318(19) 0.0031(18) 0.0074(17) -0.0015(19) C15 0.033(2) 0.069(3) 0.0285(19) 0.003(2) -0.0041(16) -0.004(2) C16 0.035(2) 0.038(2) 0.033(2) 0.0101(17) 0.0072(16) 0.0021(17) C23 0.0266(18) 0.035(2) 0.0264(17) -0.0058(15) 0.0030(14) -0.0005(15) C24 0.0267(18) 0.0272(18) 0.0323(19) -0.0015(15) 0.0030(15) -0.0001(14) C27 0.0252(17) 0.0262(17) 0.0360(19) -0.0023(15) -0.0018(15) -0.0001(14) S1 0.0221(4) 0.0300(4) 0.0237(4) 0.0015(3) 0.0002(3) 0.0036(3) O2 0.0341(15) 0.0387(16) 0.0352(15) 0.0061(12) 0.0036(12) 0.0114(13) O1 0.0301(14) 0.0419(16) 0.0292(13) -0.0039(12) -0.0026(11) -0.0022(12) O18 0.0436(17) 0.0373(15) 0.0277(14) -0.0053(12) 0.0018(12) 0.0054(13) N1 0.0232(14) 0.0336(16) 0.0226(14) 0.0024(12) 0.0019(11) 0.0039(12) _refine_ls_extinction_method 'None' _oxford_refine_ls_scale 3.61(5) 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 I1 . C8 . 2.176(4) yes C1 . C2 . 1.511(5) yes C1 . H11 . 0.958 no C1 . H13 . 0.961 no C1 . H12 . 0.957 no C2 . C3 . 1.397(6) yes C2 . C23 . 1.394(6) yes C3 . C4 . 1.390(6) yes C3 . H31 . 0.926 no C4 . C5 . 1.389(6) yes C4 . H41 . 0.935 no C5 . C24 . 1.394(5) yes C5 . S1 . 1.768(4) yes C6 . C7 . 1.554(5) yes C6 . C16 . 1.527(5) yes C6 . C27 . 1.547(5) yes C6 . S1 . 1.807(4) yes C7 . C8 . 1.555(5) yes C7 . H71 . 0.965 no C7 . H72 . 0.966 no C8 . C9 . 1.543(5) yes C8 . C27 . 1.545(5) yes C9 . O18 . 1.228(5) yes C9 . N1 . 1.358(5) yes C10 . C11 . 1.524(6) yes C10 . C12 . 1.523(5) yes C10 . N1 . 1.480(5) yes C10 . H101 . 0.983 no C11 . H112 . 0.967 no C11 . H111 . 0.961 no C11 . H113 . 0.959 no C12 . H122 . 0.957 no C12 . H121 . 0.965 no C12 . H123 . 0.966 no C13 . C14 . 1.524(5) yes C13 . C15 . 1.534(6) yes C13 . N1 . 1.484(5) yes C13 . H131 . 0.976 no C14 . H142 . 0.967 no C14 . H141 . 0.960 no C14 . H143 . 0.957 no C15 . H152 . 0.960 no C15 . H151 . 0.954 no C15 . H153 . 0.960 no C16 . H161 . 0.961 no C16 . H163 . 0.965 no C16 . H162 . 0.958 no C23 . C24 . 1.392(6) yes C23 . H231 . 0.928 no C24 . H241 . 0.919 no C27 . H271 . 0.975 no C27 . H272 . 0.955 no S1 . O2 . 1.445(3) yes S1 . O1 . 1.446(3) 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 . H11 . 109.3 no C2 . C1 . H13 . 111.0 no H11 . C1 . H13 . 109.5 no C2 . C1 . H12 . 109.7 no H11 . C1 . H12 . 108.1 no H13 . C1 . H12 . 109.1 no C1 . C2 . C3 . 120.9(4) yes C1 . C2 . C23 . 120.4(4) yes C3 . C2 . C23 . 118.8(4) yes C2 . C3 . C4 . 121.7(4) yes C2 . C3 . H31 . 119.1 no C4 . C3 . H31 . 119.2 no C3 . C4 . C5 . 118.3(4) yes C3 . C4 . H41 . 121.0 no C5 . C4 . H41 . 120.7 no C4 . C5 . C24 . 121.3(4) yes C4 . C5 . S1 . 119.7(3) yes C24 . C5 . S1 . 119.0(3) yes C7 . C6 . C16 . 115.6(3) yes C7 . C6 . C27 . 89.9(3) yes C16 . C6 . C27 . 115.1(3) yes C7 . C6 . S1 . 115.4(3) yes C16 . C6 . S1 . 106.2(3) yes C27 . C6 . S1 . 114.6(3) yes C6 . C7 . C8 . 89.2(3) yes C6 . C7 . H71 . 115.1 no C8 . C7 . H71 . 115.0 no C6 . C7 . H72 . 113.2 no C8 . C7 . H72 . 113.9 no H71 . C7 . H72 . 109.4 no C7 . C8 . I1 . 114.4(2) yes C7 . C8 . C9 . 120.3(3) yes I1 . C8 . C9 . 107.4(2) yes C7 . C8 . C27 . 89.9(3) yes I1 . C8 . C27 . 111.5(2) yes C9 . C8 . C27 . 112.4(3) yes C8 . C9 . O18 . 117.3(4) yes C8 . C9 . N1 . 119.8(3) yes O18 . C9 . N1 . 122.9(4) yes C11 . C10 . C12 . 112.4(4) yes C11 . C10 . N1 . 110.6(3) yes C12 . C10 . N1 . 111.3(4) yes C11 . C10 . H101 . 106.7 no C12 . C10 . H101 . 107.6 no N1 . C10 . H101 . 108.0 no C10 . C11 . H112 . 109.9 no C10 . C11 . H111 . 110.6 no H112 . C11 . H111 . 109.6 no C10 . C11 . H113 . 109.3 no H112 . C11 . H113 . 109.0 no H111 . C11 . H113 . 108.3 no C10 . C12 . H122 . 110.1 no C10 . C12 . H121 . 109.8 no H122 . C12 . H121 . 109.3 no C10 . C12 . H123 . 110.1 no H122 . C12 . H123 . 109.2 no H121 . C12 . H123 . 108.3 no C14 . C13 . C15 . 112.4(4) yes C14 . C13 . N1 . 112.2(3) yes C15 . C13 . N1 . 111.5(4) yes C14 . C13 . H131 . 106.6 no C15 . C13 . H131 . 106.9 no N1 . C13 . H131 . 106.9 no C13 . C14 . H142 . 109.5 no C13 . C14 . H141 . 109.3 no H142 . C14 . H141 . 109.2 no C13 . C14 . H143 . 109.7 no H142 . C14 . H143 . 109.6 no H141 . C14 . H143 . 109.5 no C13 . C15 . H152 . 110.1 no C13 . C15 . H151 . 109.8 no H152 . C15 . H151 . 108.9 no C13 . C15 . H153 . 109.3 no H152 . C15 . H153 . 109.4 no H151 . C15 . H153 . 109.2 no C6 . C16 . H161 . 108.9 no C6 . C16 . H163 . 108.9 no H161 . C16 . H163 . 109.1 no C6 . C16 . H162 . 110.2 no H161 . C16 . H162 . 109.6 no H163 . C16 . H162 . 110.1 no C2 . C23 . C24 . 120.4(4) yes C2 . C23 . H231 . 120.0 no C24 . C23 . H231 . 119.6 no C5 . C24 . C23 . 119.4(4) yes C5 . C24 . H241 . 120.3 no C23 . C24 . H241 . 120.3 no C8 . C27 . C6 . 89.8(3) yes C8 . C27 . H271 . 113.8 no C6 . C27 . H271 . 113.6 no C8 . C27 . H272 . 113.5 no C6 . C27 . H272 . 113.9 no H271 . C27 . H272 . 110.8 no C6 . S1 . C5 . 106.55(17) yes C6 . S1 . O2 . 107.84(18) yes C5 . S1 . O2 . 107.92(18) yes C6 . S1 . O1 . 107.37(18) yes C5 . S1 . O1 . 108.18(19) yes O2 . S1 . O1 . 118.41(19) yes C13 . N1 . C10 . 116.5(3) yes C13 . N1 . C9 . 118.8(3) yes C10 . N1 . C9 . 124.7(3) yes loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C1 . H11 . O2 3_565 178 0.96 2.57 3.529(6) yes C4 . H41 . O1 2_666 163 0.94 2.43 3.338(6) yes C10 . H101 . C7 . 132 0.98 2.42 3.160(6) yes _iucr_refine_instructions_details ; # # Punched on 08/09/22 at 02:30:45 # #LIST 12 BLOCK SCALE X'S U'S RIDE C ( 1,X'S) H ( 11,X'S) H ( 13,X'S) H ( 12,X'S) RIDE C ( 3,X'S) H ( 31,X'S) RIDE C ( 4,X'S) H ( 41,X'S) RIDE C ( 7,X'S) H ( 71,X'S) H ( 72,X'S) RIDE C ( 10,X'S) H ( 101,X'S) RIDE C ( 11,X'S) H ( 112,X'S) H ( 111,X'S) H ( 113,X'S) RIDE C ( 12,X'S) H ( 122,X'S) H ( 121,X'S) H ( 123,X'S) RIDE C ( 13,X'S) H ( 131,X'S) RIDE C ( 14,X'S) H ( 142,X'S) H ( 141,X'S) H ( 143,X'S) RIDE C ( 15,X'S) H ( 152,X'S) H ( 151,X'S) H ( 153,X'S) RIDE C ( 16,X'S) H ( 161,X'S) H ( 163,X'S) H ( 162,X'S) RIDE C ( 23,X'S) H ( 231,X'S) RIDE C ( 24,X'S) H ( 241,X'S) RIDE C ( 27,X'S) H ( 271,X'S) H ( 272,X'S) END # # Punched on 08/09/22 at 02:30:45 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; _refine_special_details ; ? Reflections are selected by the following conditions :- Minimum value of SQRTW is 0.00 Minimum value of RATIO is -3.00 ; #============================================================================== data_11 #============================================================================== _audit_creation_date "2022-09-08" _audit_creation_method 'CRYSTALS_ver_14.61_build_7986 ' _oxford_structure_analysis_title '7700/021eaa22' _chemical_name_systematic . _chemical_melting_point 'not measured' _cell_length_a 19.4393(4) _cell_length_b 11.5541(2) _cell_length_c 28.8409(7) _cell_angle_alpha 90 _cell_angle_beta 104.915(2) _cell_angle_gamma 90 _cell_volume 6259.5(2) _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 21/n ' _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 0.0181 0.0091 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 0.0492 0.0322 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' N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.3331 0.5567 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' Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 8 # Given Formula = C26 H37 Cl4 N1 O8 S1 # Dc = 0.18 Fooo = 348.00 Mu = 5.57 M = 665.46 # Found Formula = C215.15 H310.30 Cl14.30 N8 O64 S8 # Dc = 1.27 FOOO = 2540.32 Mu = 27.06 M = 4796.49 _chemical_formula_sum 'C26.89 H38.79 Cl1.79 N O8 S' _chemical_formula_moiety 'C26 H37 N O8 S, 0.894(C H2 Cl2)' _chemical_compound_source . _chemical_formula_weight 599.55 _cell_measurement_reflns_used 14205 _cell_measurement_theta_min 4.08 _cell_measurement_theta_max 76.13 _cell_measurement_temperature 150 _exptl_crystal_description 'block' _exptl_crystal_colour 'clear_pale_colourless' _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 2540.324 _exptl_absorpt_coefficient_mu 2.706 # Sheldrick geometric approximatio 0.72 0.81 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro (Rigaku Oxford Diffraction, 2017) ; _exptl_absorpt_correction_T_min 0.68 _exptl_absorpt_correction_T_max 0.81 _diffrn_measurement_device_type 'Oxford Diffraction SuperNova' _diffrn_measurement_device 'Area' _diffrn_radiation_monochromator 'focussing mirrors' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54180 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SuperNova, (Oxford Diffraction, 2010)' _computing_cell_refinement ; CrysAlisPro (Rigaku Oxford Diffraction, 2017) ; _computing_data_reduction ; CrysAlisPro (Rigaku Oxford Diffraction, 2017) ; _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _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 47678 _diffrn_reflns_av_unetI/netI 0.075 _reflns_number_total 12983 _diffrn_reflns_av_R_equivalents 0.045 # Number of reflections with Friedels Law is 12983 # Theoretical number of reflections is about 26277 _diffrn_reflns_theta_min 4.142 _diffrn_reflns_theta_max 76.399 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 74.107 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 35 _reflns_limit_h_min -24 _reflns_limit_h_max 23 _reflns_limit_k_min 0 _reflns_limit_k_max 14 _reflns_limit_l_min 0 _reflns_limit_l_max 36 _oxford_diffrn_Wilson_B_factor 2.68 _oxford_diffrn_Wilson_scale 0.07 _atom_sites_solution_primary other #heavy,direct,difmap,geom,iterative # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.61 _refine_diff_density_max 0.72 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # Explicitly named reflections are ALWAYS excluded from R&wR # The values actually used during refinement # These are labelled "all" for compatibility with PLATON _oxford_refine_reflns_threshold_expression I>-3.0\s(I) _refine_ls_number_restraints 176 _refine_ls_number_parameters 771 _refine_ls_number_reflns 12973 _refine_ls_R_factor_ref 0.0704 _refine_ls_wR_factor_ref 0.1437 _refine_ls_goodness_of_fit_ref 1.0003 _refine_ls_shift/su_max 0.0009806 _refine_ls_shift/su_mean 0.0000448 # Computed with I/sigma = -10 _reflns_number_all 12983 _refine_ls_R_factor_all 0.0706 _refine_ls_wR_factor_all 0.1445 # Computed with I/sigma = +2 a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 10038 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_gt 0.1269 _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr #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^) + ( 0.06P)^2^ + 5.43P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Oxford Diffraction, (2010). Supernova User Manual. Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790. Rigaku Oxford Diffraction (2017). CrysAlisPro. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached 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 0.45841(16) 0.5404(2) 0.58339(15) 0.0548 1.0000 Uani . . . . . . C2 C 0.41319(13) 0.4343(2) 0.58478(11) 0.0381 1.0000 Uani . . . . . . C3 C 0.37361(17) 0.3850(3) 0.54265(11) 0.0465 1.0000 Uani . . . . . . C4 C 0.33289(17) 0.2868(3) 0.54356(10) 0.0437 1.0000 Uani . . . . . . C5 C 0.33143(12) 0.23829(19) 0.58690(9) 0.0286 1.0000 Uani . . . . . . C6 C 0.19286(12) 0.17418(19) 0.58469(9) 0.0277 1.0000 Uani . . . . . . C7 C 0.12658(14) 0.1033(2) 0.58683(13) 0.0439 1.0000 Uani . . . . . . O8 O 0.14414(10) 0.63334(15) 0.60354(6) 0.0338 1.0000 Uani . . . . . . C8 C 0.10332(13) 0.23267(19) 0.58262(9) 0.0292 1.0000 Uani . . . . . . C9 C 0.02925(13) 0.27356(19) 0.58145(10) 0.0324 1.0000 Uani . . . . . . C10 C 0.01605(12) 0.40222(18) 0.57080(8) 0.0257 1.0000 Uani . . . . . . C11 C -0.05898(12) 0.43505(19) 0.57257(8) 0.0256 1.0000 Uani . . . . . . C12 C -0.13974(14) 0.5864(2) 0.56964(12) 0.0437 1.0000 Uani . . . . . . C13 C 0.41083(17) 0.3848(3) 0.62765(12) 0.0509 1.0000 Uani . . . . . . C14 C 0.37027(16) 0.2869(2) 0.62933(10) 0.0435 1.0000 Uani . . . . . . C15 C 0.17437(13) 0.2606(2) 0.62035(9) 0.0349 1.0000 Uani . . . . . . C16 C 0.07280(13) 0.4791(2) 0.64988(9) 0.0289 1.0000 Uani . . . . . . C17 C 0.14052(15) 0.5358(3) 0.73013(9) 0.0405 1.0000 Uani . . . . . . C18 C 0.0784(2) 0.5907(4) 0.74368(12) 0.0624 1.0000 Uani . . . . . . C19 C 0.2057(2) 0.6123(4) 0.74497(12) 0.0693 1.0000 Uani . . . . . . C20 C 0.1553(2) 0.4145(3) 0.74937(12) 0.0655 1.0000 Uani . . . . . . C21 C 0.10816(12) 0.55061(18) 0.57632(8) 0.0244 1.0000 Uani . . . . . . C22 C 0.19812(14) 0.7032(2) 0.58738(10) 0.0371 1.0000 Uani . . . . . . C23 C 0.16304(18) 0.7758(2) 0.54422(11) 0.0471 1.0000 Uani . . . . . . C24 C 0.22650(18) 0.7807(3) 0.63081(11) 0.0523 1.0000 Uani . . . . . . C25 C 0.25405(17) 0.6237(3) 0.57760(16) 0.0633 1.0000 Uani . . . . . . C27 C 0.14521(14) 0.2455(2) 0.54355(9) 0.0350 1.0000 Uani . . . . . . N1 N 0.06954(10) 0.48037(15) 0.60067(7) 0.0239 1.0000 Uani . . . . . . S1 S 0.27791(3) 0.11557(5) 0.58814(2) 0.0291 1.0000 Uani . . . . . . O1 O 0.27305(10) 0.04663(15) 0.54574(7) 0.0381 1.0000 Uani . . . . . . O2 O 0.30198(10) 0.06131(16) 0.63456(7) 0.0397 1.0000 Uani . . . . . . O3 O -0.10529(9) 0.36648(14) 0.57265(7) 0.0335 1.0000 Uani . . . . . . O4 O -0.06801(9) 0.54926(14) 0.57154(7) 0.0333 1.0000 Uani . . . . . . O5 O 0.02737(11) 0.42876(19) 0.66352(7) 0.0457 1.0000 Uani . . . . . . O6 O 0.12823(10) 0.53303(17) 0.67691(6) 0.0382 1.0000 Uani . . . . . . O7 O 0.10504(11) 0.53543(16) 0.53441(6) 0.0398 1.0000 Uani . . . . . . C101 C 0.42134(18) -0.1330(3) 0.61590(19) 0.0738 1.0000 Uani . . . . . . C102 C 0.46188(14) -0.0292(2) 0.60565(14) 0.0491 1.0000 Uani . . . . . . C103 C 0.45458(16) 0.0093(3) 0.55992(15) 0.0603 1.0000 Uani . . . . . . C104 C 0.49283(15) 0.1032(3) 0.54983(12) 0.0477 1.0000 Uani . . . . . . C105 C 0.53957(13) 0.1587(2) 0.58716(9) 0.0320 1.0000 Uani . . . . . . C106 C 0.67438(12) 0.2153(2) 0.57714(9) 0.0282 1.0000 Uani . . . . . . C107 C 0.73915(13) 0.2868(2) 0.57181(10) 0.0346 1.0000 Uani . . . . . . O108 O 0.71733(8) -0.16625(14) 0.62738(6) 0.0291 1.0000 Uani . . . . . . C108 C 0.76470(12) 0.15830(19) 0.57999(8) 0.0267 1.0000 Uani . . . . . . C109 C 0.83856(12) 0.11655(19) 0.58204(9) 0.0288 1.0000 Uani . . . . . . C110 C 0.84476(12) -0.01512(19) 0.58120(9) 0.0280 1.0000 Uani . . . . . . C111 C 0.92084(14) -0.0518(2) 0.58365(10) 0.0363 1.0000 Uani . . . . . . C112 C 1.00592(16) -0.2002(3) 0.60420(17) 0.0651 1.0000 Uani . . . . . . C113 C 0.50894(19) 0.0281(3) 0.64304(13) 0.0518 1.0000 Uani . . . . . . C114 C 0.54772(18) 0.1219(2) 0.63398(11) 0.0456 1.0000 Uani . . . . . . C115 C 0.72403(13) 0.1526(2) 0.62023(9) 0.0311 1.0000 Uani . . . . . . C116 C 0.85250(13) -0.0593(2) 0.66516(9) 0.0302 1.0000 Uani . . . . . . C117 C 0.85806(17) -0.1235(3) 0.74637(9) 0.0459 1.0000 Uani . . . . . . C118 C 0.93370(19) -0.1681(4) 0.75839(14) 0.0796 1.0000 Uani . . . . . . C119 C 0.81014(19) -0.2063(3) 0.76410(11) 0.0594 1.0000 Uani . . . . . . C120 C 0.8524(3) -0.0031(4) 0.76516(15) 0.0927 1.0000 Uani . . . . . . C121 C 0.76003(11) -0.15380(18) 0.59872(8) 0.0243 1.0000 Uani . . . . . . C122 C 0.65771(12) -0.2517(2) 0.61513(9) 0.0304 1.0000 Uani . . . . . . C123 C 0.68639(15) -0.3718(2) 0.61020(12) 0.0449 1.0000 Uani . . . . . . C124 C 0.62847(15) -0.2436(3) 0.65905(10) 0.0431 1.0000 Uani . . . . . . C125 C 0.60320(13) -0.2109(2) 0.57078(10) 0.0374 1.0000 Uani . . . . . . C127 C 0.69323(13) 0.1227(2) 0.54388(9) 0.0339 1.0000 Uani . . . . . . N101 N 0.81549(10) -0.07399(16) 0.61715(7) 0.0251 1.0000 Uani . . . . . . S101 S 0.59031(3) 0.27647(5) 0.57542(2) 0.0330 1.0000 Uani . . . . . . O101 O 0.55966(11) 0.3178(2) 0.52762(8) 0.0511 1.0000 Uani . . . . . . O102 O 0.60083(10) 0.35626(15) 0.61515(8) 0.0428 1.0000 Uani . . . . . . O103 O 0.96093(13) 0.0047(2) 0.56774(11) 0.0680 1.0000 Uani . . . . . . O104 O 0.93577(10) -0.15670(16) 0.60269(8) 0.0445 1.0000 Uani . . . . . . O105 O 0.90153(11) 0.00709(17) 0.67623(7) 0.0430 1.0000 Uani . . . . . . O106 O 0.82833(10) -0.12793(16) 0.69397(6) 0.0383 1.0000 Uani . . . . . . O107 O 0.75301(9) -0.19770(15) 0.56007(6) 0.0325 1.0000 Uani . . . . . . C201 C 1.0722(3) 0.0786(4) 0.72619(13) 0.0712 0.685(6) Uani D . P 1 1 . Cl202 Cl 1.10869(13) -0.0523(3) 0.71647(11) 0.0980 0.685(6) Uani D . P 1 1 . Cl203 Cl 1.09555(18) 0.11915(19) 0.78651(7) 0.0824 0.685(6) Uani D . P 1 1 . C211 C 0.8932(4) 0.3453(6) 0.69365(13) 0.0803 0.585(4) Uani D . P 1 2 . Cl212 Cl 0.95363(12) 0.29578(15) 0.74461(6) 0.0663 0.585(4) Uani D . P 1 2 . Cl213 Cl 0.8525(2) 0.4721(5) 0.70331(13) 0.1316 0.585(4) Uani D . P 1 2 . C221 C 0.8816(11) 0.4050(7) 0.6865(3) 0.0803 0.268(4) Uani D . P 1 3 . Cl222 Cl 0.8962(4) 0.2796(5) 0.7184(3) 0.1147 0.268(4) Uani D . P 1 3 . Cl223 Cl 0.8650(4) 0.5187(5) 0.7195(3) 0.1142 0.268(4) Uani D . P 1 3 . C231 C 1.0511(13) 0.1198(19) 0.7205(3) 0.0712 0.168(6) Uani D . P 1 4 . Cl232 Cl 1.1056(6) 0.0063(13) 0.7152(4) 0.1032 0.168(6) Uani D . P 1 4 . Cl233 Cl 1.0532(7) 0.1506(9) 0.7796(3) 0.0854 0.168(6) Uani D . P 1 4 . C241 C 0.933(3) 0.287(5) 0.7092(7) 0.1147 0.082(3) Uani D . P 1 5 . Cl242 Cl 0.8749(12) 0.3921(19) 0.7180(9) 0.1223 0.082(3) Uani D . P 1 5 . Cl243 Cl 0.9902(11) 0.2406(17) 0.7622(8) 0.1128 0.082(3) Uani D . P 1 5 . H11 H 0.4671 0.5785 0.6131 0.0829 1.0000 Uiso R . . . . . H12 H 0.5026 0.5208 0.5774 0.0831 1.0000 Uiso R . . . . . H13 H 0.4337 0.5925 0.5594 0.0824 1.0000 Uiso R . . . . . H31 H 0.3748 0.4189 0.5132 0.0571 1.0000 Uiso R . . . . . H41 H 0.3058 0.2551 0.5151 0.0521 1.0000 Uiso R . . . . . H71 H 0.1278 0.0654 0.6167 0.0529 1.0000 Uiso R . . . . . H72 H 0.1061 0.0528 0.5594 0.0533 1.0000 Uiso R . . . . . H91 H 0.0199 0.2557 0.6120 0.0394 1.0000 Uiso R . . . . . H92 H -0.0049 0.2300 0.5557 0.0392 1.0000 Uiso R . . . . . H101 H 0.0183 0.4143 0.5380 0.0302 1.0000 Uiso R . . . . . H121 H -0.1413 0.6697 0.5662 0.0644 1.0000 Uiso R . . . . . H122 H -0.1499 0.5640 0.5995 0.0643 1.0000 Uiso R . . . . . H123 H -0.1734 0.5512 0.5415 0.0645 1.0000 Uiso R . . . . . H131 H 0.4367 0.4179 0.6564 0.0609 1.0000 Uiso R . . . . . H141 H 0.3691 0.2544 0.6584 0.0524 1.0000 Uiso R . . . . . H151 H 0.1800 0.2331 0.6533 0.0423 1.0000 Uiso R . . . . . H152 H 0.1940 0.3376 0.6199 0.0422 1.0000 Uiso R . . . . . H181 H 0.0902 0.5998 0.7781 0.0924 1.0000 Uiso R . . . . . H182 H 0.0681 0.6654 0.7287 0.0932 1.0000 Uiso R . . . . . H183 H 0.0361 0.5422 0.7339 0.0926 1.0000 Uiso R . . . . . H191 H 0.2220 0.6138 0.7798 0.1041 1.0000 Uiso R . . . . . H192 H 0.2431 0.5783 0.7320 0.1036 1.0000 Uiso R . . . . . H193 H 0.1943 0.6896 0.7326 0.1042 1.0000 Uiso R . . . . . H201 H 0.1712 0.4174 0.7839 0.0975 1.0000 Uiso R . . . . . H202 H 0.1923 0.3809 0.7374 0.0982 1.0000 Uiso R . . . . . H203 H 0.1127 0.3686 0.7393 0.0976 1.0000 Uiso R . . . . . H231 H 0.1976 0.8317 0.5386 0.0704 1.0000 Uiso R . . . . . H232 H 0.1224 0.8181 0.5499 0.0705 1.0000 Uiso R . . . . . H233 H 0.1470 0.7273 0.5160 0.0709 1.0000 Uiso R . . . . . H241 H 0.2599 0.8364 0.6239 0.0787 1.0000 Uiso R . . . . . H242 H 0.2525 0.7302 0.6574 0.0788 1.0000 Uiso R . . . . . H243 H 0.1874 0.8219 0.6398 0.0790 1.0000 Uiso R . . . . . H251 H 0.2929 0.6683 0.5716 0.0948 1.0000 Uiso R . . . . . H252 H 0.2725 0.5747 0.6053 0.0954 1.0000 Uiso R . . . . . H253 H 0.2355 0.5767 0.5496 0.0931 1.0000 Uiso R . . . . . H271 H 0.1613 0.3227 0.5384 0.0421 1.0000 Uiso R . . . . . H272 H 0.1267 0.2057 0.5133 0.0431 1.0000 Uiso R . . . . . H1011 H 0.4513 -0.1827 0.6382 0.1112 1.0000 Uiso R . . . . . H1012 H 0.4029 -0.1738 0.5867 0.1115 1.0000 Uiso R . . . . . H1013 H 0.3833 -0.1080 0.6283 0.1118 1.0000 Uiso R . . . . . H1031 H 0.4224 -0.0267 0.5346 0.0722 1.0000 Uiso R . . . . . H1041 H 0.4872 0.1290 0.5193 0.0569 1.0000 Uiso R . . . . . H1071 H 0.7596 0.3417 0.5975 0.0420 1.0000 Uiso R . . . . . H1072 H 0.7361 0.3211 0.5405 0.0419 1.0000 Uiso R . . . . . H1091 H 0.8710 0.1476 0.6107 0.0345 1.0000 Uiso R . . . . . H1092 H 0.8508 0.1448 0.5537 0.0351 1.0000 Uiso R . . . . . H1101 H 0.8161 -0.0409 0.5494 0.0340 1.0000 Uiso R . . . . . H1121 H 1.0120 -0.2718 0.6215 0.0978 1.0000 Uiso R . . . . . H1122 H 1.0409 -0.1458 0.6213 0.0978 1.0000 Uiso R . . . . . H1123 H 1.0101 -0.2120 0.5716 0.0980 1.0000 Uiso R . . . . . H1131 H 0.5143 0.0047 0.6746 0.0622 1.0000 Uiso R . . . . . H1141 H 0.5792 0.1590 0.6594 0.0556 1.0000 Uiso R . . . . . H1151 H 0.7426 0.1970 0.6488 0.0364 1.0000 Uiso R . . . . . H1152 H 0.7099 0.0778 0.6286 0.0371 1.0000 Uiso R . . . . . H1181 H 0.9506 -0.1762 0.7923 0.1188 1.0000 Uiso R . . . . . H1182 H 0.9624 -0.1121 0.7471 0.1187 1.0000 Uiso R . . . . . H1183 H 0.9347 -0.2424 0.7431 0.1191 1.0000 Uiso R . . . . . H1191 H 0.8247 -0.2090 0.7989 0.0883 1.0000 Uiso R . . . . . H1192 H 0.8151 -0.2841 0.7518 0.0882 1.0000 Uiso R . . . . . H1193 H 0.7608 -0.1810 0.7539 0.0887 1.0000 Uiso R . . . . . H1201 H 0.8642 -0.0064 0.8000 0.1387 1.0000 Uiso R . . . . . H1202 H 0.8853 0.0461 0.7543 0.1387 1.0000 Uiso R . . . . . H1203 H 0.8032 0.0225 0.7521 0.1385 1.0000 Uiso R . . . . . H1231 H 0.6488 -0.4277 0.6083 0.0664 1.0000 Uiso R . . . . . H1232 H 0.7253 -0.3897 0.6376 0.0664 1.0000 Uiso R . . . . . H1233 H 0.7027 -0.3782 0.5819 0.0660 1.0000 Uiso R . . . . . H1241 H 0.5879 -0.2950 0.6554 0.0647 1.0000 Uiso R . . . . . H1242 H 0.6640 -0.2643 0.6882 0.0646 1.0000 Uiso R . . . . . H1243 H 0.6130 -0.1643 0.6623 0.0644 1.0000 Uiso R . . . . . H1251 H 0.5626 -0.2611 0.5647 0.0557 1.0000 Uiso R . . . . . H1252 H 0.5881 -0.1328 0.5752 0.0563 1.0000 Uiso R . . . . . H1253 H 0.6233 -0.2131 0.5436 0.0550 1.0000 Uiso R . . . . . H1271 H 0.6774 0.0442 0.5470 0.0414 1.0000 Uiso R . . . . . H1272 H 0.6876 0.1432 0.5105 0.0408 1.0000 Uiso R . . . . . H2011 H 1.0888 0.1351 0.7085 0.0848 0.685(6) Uiso R . P 1 1 . H2012 H 1.0219 0.0724 0.7156 0.0851 0.685(6) Uiso R . P 1 1 . H2111 H 0.9168 0.3569 0.6679 0.0969 0.585(4) Uiso R . P 1 2 . H2112 H 0.8563 0.2864 0.6851 0.0971 0.585(4) Uiso R . P 1 2 . H2211 H 0.9236 0.4236 0.6755 0.0969 0.268(4) Uiso R . P 1 3 . H2212 H 0.8407 0.3959 0.6590 0.0973 0.268(4) Uiso R . P 1 3 . H2311 H 1.0664 0.1876 0.7063 0.0850 0.168(6) Uiso R . P 1 4 . H2312 H 1.0028 0.1008 0.7033 0.0852 0.168(6) Uiso R . P 1 4 . H2411 H 0.9611 0.3173 0.6888 0.1380 0.082(3) Uiso R . P 1 5 . H2412 H 0.9055 0.2207 0.6935 0.1380 0.082(3) Uiso R . P 1 5 . 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 0.0375(15) 0.0281(13) 0.095(3) -0.0011(14) 0.0102(16) -0.0043(11) C2 0.0279(12) 0.0254(11) 0.0592(17) -0.0014(11) 0.0080(11) 0.0025(10) C3 0.0587(18) 0.0416(15) 0.0451(16) -0.0038(12) 0.0241(14) -0.0132(13) C4 0.0545(17) 0.0441(15) 0.0368(14) -0.0136(12) 0.0197(12) -0.0181(13) C5 0.0246(11) 0.0232(10) 0.0381(13) -0.0025(9) 0.0081(9) 0.0024(8) C6 0.0254(11) 0.0226(10) 0.0364(12) -0.0002(9) 0.0105(9) 0.0013(8) C7 0.0316(13) 0.0244(12) 0.079(2) 0.0033(12) 0.0197(13) 0.0006(10) O8 0.0400(9) 0.0325(9) 0.0304(9) -0.0047(7) 0.0119(7) -0.0155(7) C8 0.0278(11) 0.0193(10) 0.0412(13) -0.0006(9) 0.0100(10) -0.0020(9) C9 0.0268(11) 0.0214(10) 0.0497(15) -0.0003(10) 0.0112(10) -0.0015(9) C10 0.0255(11) 0.0209(10) 0.0312(11) -0.0031(8) 0.0080(9) -0.0038(8) C11 0.0269(11) 0.0226(10) 0.0263(11) -0.0009(8) 0.0049(8) -0.0020(9) C12 0.0308(13) 0.0314(13) 0.070(2) -0.0016(12) 0.0160(13) 0.0061(10) C13 0.0508(17) 0.0376(14) 0.0496(17) -0.0004(13) -0.0137(13) -0.0084(13) C14 0.0494(16) 0.0353(13) 0.0370(14) 0.0046(11) -0.0050(12) -0.0038(12) C15 0.0316(12) 0.0365(13) 0.0362(13) -0.0064(10) 0.0078(10) 0.0065(10) C16 0.0285(11) 0.0284(11) 0.0303(11) -0.0002(9) 0.0084(9) -0.0056(9) C17 0.0436(15) 0.0499(15) 0.0256(12) 0.0005(11) 0.0043(10) -0.0125(12) C18 0.067(2) 0.076(2) 0.0432(17) -0.0196(16) 0.0127(15) -0.0043(19) C19 0.067(2) 0.100(3) 0.0338(16) -0.0039(17) 0.0013(15) -0.044(2) C20 0.091(3) 0.059(2) 0.0369(16) 0.0095(15) 0.0001(17) 0.0087(19) C21 0.0242(10) 0.0188(9) 0.0299(11) -0.0009(8) 0.0066(8) -0.0012(8) C22 0.0360(13) 0.0376(13) 0.0393(14) -0.0018(11) 0.0128(11) -0.0159(11) C23 0.0594(18) 0.0347(14) 0.0486(16) 0.0058(12) 0.0167(14) -0.0155(13) C24 0.0573(18) 0.0512(17) 0.0474(17) -0.0073(14) 0.0116(14) -0.0292(15) C25 0.0395(16) 0.0483(18) 0.109(3) 0.0030(18) 0.0315(18) -0.0053(14) C27 0.0348(13) 0.0366(13) 0.0334(13) 0.0006(10) 0.0083(10) 0.0062(10) N1 0.0219(8) 0.0217(8) 0.0276(9) -0.0011(7) 0.0055(7) -0.0035(7) S1 0.0278(3) 0.0223(2) 0.0384(3) -0.0023(2) 0.0106(2) 0.0016(2) O1 0.0374(9) 0.0292(8) 0.0506(11) -0.0121(8) 0.0165(8) -0.0022(7) O2 0.0391(10) 0.0329(9) 0.0470(11) 0.0082(8) 0.0113(8) 0.0064(8) O3 0.0257(8) 0.0256(8) 0.0499(10) 0.0015(7) 0.0110(7) -0.0041(7) O4 0.0264(8) 0.0227(8) 0.0509(10) -0.0019(7) 0.0103(7) 0.0000(6) O5 0.0453(11) 0.0617(12) 0.0320(9) -0.0029(9) 0.0135(8) -0.0247(10) O6 0.0381(9) 0.0487(10) 0.0253(8) 0.0019(7) 0.0035(7) -0.0175(8) O7 0.0511(11) 0.0383(9) 0.0322(9) -0.0045(7) 0.0149(8) -0.0194(8) C101 0.0433(18) 0.0305(15) 0.157(4) 0.0043(19) 0.042(2) -0.0016(13) C102 0.0279(13) 0.0265(12) 0.099(3) -0.0024(14) 0.0269(15) 0.0025(10) C103 0.0315(14) 0.0465(17) 0.087(3) -0.0028(17) -0.0129(15) -0.0077(13) C104 0.0336(14) 0.0454(15) 0.0530(17) 0.0050(13) -0.0090(12) -0.0018(12) C105 0.0275(11) 0.0265(11) 0.0442(14) -0.0022(10) 0.0131(10) 0.0011(9) C106 0.0243(11) 0.0259(10) 0.0342(12) 0.0018(9) 0.0073(9) -0.0014(9) C107 0.0304(12) 0.0274(11) 0.0475(14) 0.0077(10) 0.0126(10) -0.0015(10) O108 0.0256(8) 0.0305(8) 0.0326(8) -0.0008(7) 0.0100(6) -0.0078(6) C108 0.0260(11) 0.0247(10) 0.0304(11) 0.0028(9) 0.0087(9) -0.0033(9) C109 0.0273(11) 0.0251(10) 0.0353(12) 0.0033(9) 0.0102(9) -0.0045(9) C110 0.0271(11) 0.0260(11) 0.0333(12) -0.0001(9) 0.0123(9) -0.0046(9) C111 0.0321(13) 0.0276(11) 0.0535(16) -0.0084(11) 0.0186(11) -0.0040(10) C112 0.0320(15) 0.0398(16) 0.123(3) -0.0134(18) 0.0191(18) 0.0024(13) C113 0.070(2) 0.0361(14) 0.063(2) -0.0050(13) 0.0423(17) -0.0086(14) C114 0.0607(18) 0.0392(14) 0.0435(15) -0.0113(12) 0.0256(14) -0.0150(13) C115 0.0302(12) 0.0324(12) 0.0319(12) 0.0030(9) 0.0105(9) 0.0045(10) C116 0.0301(12) 0.0280(11) 0.0315(12) 0.0012(9) 0.0062(9) -0.0021(9) C117 0.0523(17) 0.0557(17) 0.0257(13) 0.0060(12) 0.0026(11) -0.0158(14) C118 0.0475(19) 0.118(4) 0.061(2) 0.044(2) -0.0080(16) -0.017(2) C119 0.0567(19) 0.082(2) 0.0362(15) 0.0168(16) 0.0061(14) -0.0193(18) C120 0.174(5) 0.066(2) 0.049(2) -0.0128(18) 0.049(3) -0.025(3) C121 0.0238(10) 0.0198(9) 0.0291(11) 0.0036(8) 0.0064(8) 0.0015(8) C122 0.0249(11) 0.0270(11) 0.0395(13) 0.0024(9) 0.0087(10) -0.0056(9) C123 0.0386(14) 0.0264(12) 0.071(2) 0.0061(12) 0.0174(14) -0.0023(11) C124 0.0358(14) 0.0542(16) 0.0425(15) 0.0040(12) 0.0157(12) -0.0140(12) C125 0.0244(11) 0.0450(14) 0.0407(14) 0.0033(11) 0.0044(10) -0.0022(10) C127 0.0297(12) 0.0366(13) 0.0350(13) -0.0035(10) 0.0075(10) -0.0033(10) N101 0.0244(9) 0.0236(8) 0.0267(9) 0.0002(7) 0.0058(7) -0.0040(7) S101 0.0276(3) 0.0283(3) 0.0434(3) 0.0061(2) 0.0097(2) 0.0020(2) O101 0.0365(10) 0.0605(13) 0.0553(13) 0.0228(10) 0.0098(9) 0.0095(9) O102 0.0407(10) 0.0265(8) 0.0633(13) -0.0048(8) 0.0173(9) -0.0001(8) O103 0.0506(13) 0.0449(12) 0.128(2) 0.0117(13) 0.0578(15) 0.0024(10) O104 0.0304(9) 0.0274(9) 0.0770(14) -0.0021(9) 0.0160(9) 0.0019(7) O105 0.0457(11) 0.0442(10) 0.0344(10) 0.0001(8) 0.0020(8) -0.0212(9) O106 0.0399(10) 0.0445(10) 0.0274(9) 0.0056(7) 0.0029(7) -0.0133(8) O107 0.0329(9) 0.0326(8) 0.0334(9) -0.0062(7) 0.0110(7) -0.0064(7) C201 0.073(3) 0.062(3) 0.078(2) -0.009(2) 0.018(2) -0.021(2) Cl202 0.0790(12) 0.0807(16) 0.1328(18) -0.0329(14) 0.0244(11) -0.0019(11) Cl203 0.0995(19) 0.0839(12) 0.0603(9) -0.0059(8) 0.0143(10) -0.0120(11) C211 0.075(3) 0.106(3) 0.068(3) -0.000(3) 0.035(2) -0.002(3) Cl212 0.0889(14) 0.0602(10) 0.0584(10) 0.0023(7) 0.0343(9) -0.0132(9) Cl213 0.114(3) 0.183(4) 0.099(2) 0.022(2) 0.0294(18) 0.064(3) C221 0.075(3) 0.106(3) 0.068(3) -0.000(3) 0.035(2) -0.002(3) Cl222 0.126(4) 0.097(3) 0.132(4) 0.024(3) 0.053(4) 0.017(3) Cl223 0.081(3) 0.096(3) 0.147(5) -0.051(3) -0.005(3) 0.021(3) C231 0.073(3) 0.062(3) 0.078(2) -0.009(2) 0.018(2) -0.021(2) Cl232 0.102(5) 0.099(6) 0.106(5) -0.001(5) 0.022(4) -0.004(5) Cl233 0.084(5) 0.088(4) 0.079(4) -0.000(3) 0.013(4) -0.018(4) C241 0.126(4) 0.097(3) 0.132(4) 0.024(3) 0.053(4) 0.017(3) Cl242 0.127(7) 0.106(7) 0.144(8) 0.011(7) 0.054(7) 0.016(6) Cl243 0.127(7) 0.100(7) 0.123(7) 0.018(6) 0.054(6) -0.004(6) _refine_ls_extinction_method 'None' _oxford_refine_ls_scale 1.282(5) 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 . 1.515(4) yes C1 . H11 . 0.939 no C1 . H12 . 0.945 no C1 . H13 . 0.949 no C2 . C3 . 1.383(4) yes C2 . C13 . 1.374(4) yes C3 . C4 . 1.387(4) yes C3 . H31 . 0.942 no C4 . C5 . 1.377(4) yes C4 . H41 . 0.928 no C5 . C14 . 1.381(4) yes C5 . S1 . 1.765(2) yes C6 . C7 . 1.541(3) yes C6 . C8 . 1.854(3) yes C6 . C15 . 1.541(3) yes C6 . C27 . 1.542(3) yes C6 . S1 . 1.766(2) yes C7 . C8 . 1.557(3) yes C7 . H71 . 0.963 no C7 . H72 . 0.980 no O8 . C21 . 1.318(3) yes O8 . C22 . 1.490(3) yes C8 . C9 . 1.507(3) yes C8 . C15 . 1.556(3) yes C8 . C27 . 1.558(3) yes C9 . C10 . 1.526(3) yes C9 . H91 . 0.967 no C9 . H92 . 0.996 no C10 . C11 . 1.520(3) yes C10 . N1 . 1.476(3) yes C10 . H101 . 0.968 no C11 . O3 . 1.200(3) yes C11 . O4 . 1.331(3) yes C12 . O4 . 1.447(3) yes C12 . H121 . 0.967 no C12 . H122 . 0.966 no C12 . H123 . 0.989 no C13 . C14 . 1.387(4) yes C13 . H131 . 0.933 no C14 . H141 . 0.924 no C15 . H151 . 0.982 no C15 . H152 . 0.969 no C16 . N1 . 1.404(3) yes C16 . O5 . 1.205(3) yes C16 . O6 . 1.313(3) yes C17 . C18 . 1.503(5) yes C17 . C19 . 1.514(4) yes C17 . C20 . 1.507(4) yes C17 . O6 . 1.492(3) yes C18 . H181 . 0.966 no C18 . H182 . 0.963 no C18 . H183 . 0.975 no C19 . H191 . 0.972 no C19 . H192 . 0.982 no C19 . H193 . 0.967 no C20 . H201 . 0.964 no C20 . H202 . 0.956 no C20 . H203 . 0.963 no C21 . N1 . 1.410(3) yes C21 . O7 . 1.208(3) yes C22 . C23 . 1.510(4) yes C22 . C24 . 1.523(4) yes C22 . C25 . 1.505(4) yes C23 . H231 . 0.976 no C23 . H232 . 0.979 no C23 . H233 . 0.971 no C24 . H241 . 0.970 no C24 . H242 . 0.992 no C24 . H243 . 0.986 no C25 . H251 . 0.967 no C25 . H252 . 0.969 no C25 . H253 . 0.963 no C27 . H271 . 0.969 no C27 . H272 . 0.969 no S1 . O1 . 1.4419(18) yes S1 . O2 . 1.4429(19) yes C101 . C102 . 1.506(4) yes C101 . H1011 . 0.942 no C101 . H1012 . 0.950 no C101 . H1013 . 0.947 no C102 . C103 . 1.364(5) yes C102 . C113 . 1.390(5) yes C103 . C104 . 1.388(4) yes C103 . H1031 . 0.930 no C104 . C105 . 1.376(4) yes C104 . H1041 . 0.908 no C105 . C114 . 1.385(4) yes C105 . S101 . 1.764(2) yes C106 . C107 . 1.546(3) yes C106 . C108 . 1.857(3) yes C106 . C115 . 1.544(3) yes C106 . C127 . 1.543(3) yes C106 . S101 . 1.769(2) yes C107 . C108 . 1.564(3) yes C107 . H1071 . 0.978 no C107 . H1072 . 0.975 no O108 . C121 . 1.321(3) yes O108 . C122 . 1.494(3) yes C108 . C109 . 1.501(3) yes C108 . C115 . 1.565(3) yes C108 . C127 . 1.562(3) yes C109 . C110 . 1.527(3) yes C109 . H1091 . 0.971 no C109 . H1092 . 0.965 no C110 . C111 . 1.523(3) yes C110 . N101 . 1.472(3) yes C110 . H1101 . 0.988 no C111 . O103 . 1.195(3) yes C111 . O104 . 1.331(3) yes C112 . O104 . 1.443(3) yes C112 . H1121 . 0.956 no C112 . H1122 . 0.964 no C112 . H1123 . 0.973 no C113 . C114 . 1.383(4) yes C113 . H1131 . 0.931 no C114 . H1141 . 0.929 no C115 . H1151 . 0.958 no C115 . H1152 . 0.958 no C116 . N101 . 1.397(3) yes C116 . O105 . 1.201(3) yes C116 . O106 . 1.319(3) yes C117 . C118 . 1.512(5) yes C117 . C119 . 1.513(4) yes C117 . C120 . 1.508(5) yes C117 . O106 . 1.473(3) yes C118 . H1181 . 0.954 no C118 . H1182 . 0.964 no C118 . H1183 . 0.967 no C119 . H1191 . 0.971 no C119 . H1192 . 0.980 no C119 . H1193 . 0.974 no C120 . H1201 . 0.972 no C120 . H1202 . 0.967 no C120 . H1203 . 0.979 no C121 . N101 . 1.414(3) yes C121 . O107 . 1.200(3) yes C122 . C123 . 1.516(3) yes C122 . C124 . 1.519(4) yes C122 . C125 . 1.511(3) yes C123 . H1231 . 0.967 no C123 . H1232 . 0.965 no C123 . H1233 . 0.951 no C124 . H1241 . 0.972 no C124 . H1242 . 0.971 no C124 . H1243 . 0.976 no C125 . H1251 . 0.959 no C125 . H1252 . 0.967 no C125 . H1253 . 0.962 no C127 . H1271 . 0.969 no C127 . H1272 . 0.971 no S101 . O101 . 1.436(2) yes S101 . O102 . 1.444(2) yes C201 . Cl202 . 1.725(4) yes C201 . Cl203 . 1.745(4) yes C201 . H2011 . 0.937 no C201 . H2012 . 0.948 no C211 . Cl212 . 1.726(5) yes C211 . Cl213 . 1.721(5) yes C211 . H2111 . 0.979 no C211 . H2112 . 0.974 no C221 . Cl222 . 1.701(6) yes C221 . Cl223 . 1.700(6) yes C221 . H2211 . 0.973 no C221 . H2212 . 0.974 no C231 . Cl232 . 1.717(7) yes C231 . Cl233 . 1.732(7) yes C231 . H2311 . 0.966 no C231 . H2312 . 0.966 no C241 . Cl242 . 1.722(7) yes C241 . Cl243 . 1.730(7) yes C241 . H2411 . 0.971 no C241 . H2412 . 0.971 no 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 . H11 . 108.9 no C2 . C1 . H12 . 111.8 no H11 . C1 . H12 . 108.6 no C2 . C1 . H13 . 110.2 no H11 . C1 . H13 . 107.9 no H12 . C1 . H13 . 109.3 no C1 . C2 . C3 . 120.4(3) yes C1 . C2 . C13 . 121.0(3) yes C3 . C2 . C13 . 118.6(3) yes C2 . C3 . C4 . 120.8(3) yes C2 . C3 . H31 . 119.0 no C4 . C3 . H31 . 120.3 no C3 . C4 . C5 . 119.7(3) yes C3 . C4 . H41 . 120.2 no C5 . C4 . H41 . 120.1 no C4 . C5 . C14 . 120.3(2) yes C4 . C5 . S1 . 119.71(19) yes C14 . C5 . S1 . 120.0(2) yes C7 . C6 . C8 . 53.65(13) yes C7 . C6 . C15 . 88.66(19) yes C8 . C6 . C15 . 53.62(13) yes C7 . C6 . C27 . 88.40(19) yes C8 . C6 . C27 . 53.67(14) yes C15 . C6 . C27 . 88.29(18) yes C7 . C6 . S1 . 125.05(17) yes C8 . C6 . S1 . 178.20(16) yes C15 . C6 . S1 . 125.93(18) yes C27 . C6 . S1 . 128.06(17) yes C6 . C7 . C8 . 73.50(16) yes C6 . C7 . H71 . 116.8 no C8 . C7 . H71 . 116.5 no C6 . C7 . H72 . 117.0 no C8 . C7 . H72 . 117.3 no H71 . C7 . H72 . 111.2 no C21 . O8 . C22 . 121.00(19) yes C7 . C8 . C6 . 52.85(13) yes C7 . C8 . C9 . 124.0(2) yes C6 . C8 . C9 . 176.83(19) yes C7 . C8 . C15 . 87.54(19) yes C6 . C8 . C15 . 52.86(13) yes C9 . C8 . C15 . 128.4(2) yes C7 . C8 . C27 . 87.27(19) yes C6 . C8 . C27 . 52.89(14) yes C9 . C8 . C27 . 128.9(2) yes C15 . C8 . C27 . 87.19(18) yes C8 . C9 . C10 . 114.82(19) yes C8 . C9 . H91 . 108.4 no C10 . C9 . H91 . 109.3 no C8 . C9 . H92 . 107.9 no C10 . C9 . H92 . 107.3 no H91 . C9 . H92 . 109.1 no C9 . C10 . C11 . 110.44(18) yes C9 . C10 . N1 . 114.95(19) yes C11 . C10 . N1 . 111.45(17) yes C9 . C10 . H101 . 106.8 no C11 . C10 . H101 . 106.4 no N1 . C10 . H101 . 106.2 no C10 . C11 . O3 . 124.2(2) yes C10 . C11 . O4 . 111.65(18) yes O3 . C11 . O4 . 124.1(2) yes O4 . C12 . H121 . 107.6 no O4 . C12 . H122 . 107.6 no H121 . C12 . H122 . 110.6 no O4 . C12 . H123 . 109.7 no H121 . C12 . H123 . 109.2 no H122 . C12 . H123 . 112.1 no C2 . C13 . C14 . 121.5(3) yes C2 . C13 . H131 . 119.5 no C14 . C13 . H131 . 119.0 no C13 . C14 . C5 . 119.1(3) yes C13 . C14 . H141 . 120.7 no C5 . C14 . H141 . 120.2 no C6 . C15 . C8 . 73.52(16) yes C6 . C15 . H151 . 116.7 no C8 . C15 . H151 . 117.9 no C6 . C15 . H152 . 115.2 no C8 . C15 . H152 . 117.5 no H151 . C15 . H152 . 111.4 no N1 . C16 . O5 . 119.3(2) yes N1 . C16 . O6 . 114.30(19) yes O5 . C16 . O6 . 126.4(2) yes C18 . C17 . C19 . 110.5(3) yes C18 . C17 . C20 . 112.8(3) yes C19 . C17 . C20 . 111.8(3) yes C18 . C17 . O6 . 110.5(2) yes C19 . C17 . O6 . 101.8(2) yes C20 . C17 . O6 . 108.9(2) yes C17 . C18 . H181 . 108.6 no C17 . C18 . H182 . 110.4 no H181 . C18 . H182 . 109.3 no C17 . C18 . H183 . 110.9 no H181 . C18 . H183 . 108.7 no H182 . C18 . H183 . 108.9 no C17 . C19 . H191 . 109.2 no C17 . C19 . H192 . 107.9 no H191 . C19 . H192 . 109.0 no C17 . C19 . H193 . 109.9 no H191 . C19 . H193 . 110.3 no H192 . C19 . H193 . 110.5 no C17 . C20 . H201 . 109.1 no C17 . C20 . H202 . 109.5 no H201 . C20 . H202 . 108.4 no C17 . C20 . H203 . 109.5 no H201 . C20 . H203 . 110.7 no H202 . C20 . H203 . 109.6 no O8 . C21 . N1 . 112.96(19) yes O8 . C21 . O7 . 125.7(2) yes N1 . C21 . O7 . 121.3(2) yes O8 . C22 . C23 . 110.7(2) yes O8 . C22 . C24 . 101.3(2) yes C23 . C22 . C24 . 110.0(2) yes O8 . C22 . C25 . 109.2(2) yes C23 . C22 . C25 . 112.3(3) yes C24 . C22 . C25 . 112.8(3) yes C22 . C23 . H231 . 108.7 no C22 . C23 . H232 . 110.6 no H231 . C23 . H232 . 108.5 no C22 . C23 . H233 . 110.5 no H231 . C23 . H233 . 109.2 no H232 . C23 . H233 . 109.3 no C22 . C24 . H241 . 110.0 no C22 . C24 . H242 . 107.1 no H241 . C24 . H242 . 108.3 no C22 . C24 . H243 . 111.1 no H241 . C24 . H243 . 109.7 no H242 . C24 . H243 . 110.7 no C22 . C25 . H251 . 110.1 no C22 . C25 . H252 . 109.5 no H251 . C25 . H252 . 108.7 no C22 . C25 . H253 . 111.7 no H251 . C25 . H253 . 106.9 no H252 . C25 . H253 . 109.9 no C6 . C27 . C8 . 73.44(17) yes C6 . C27 . H271 . 117.1 no C8 . C27 . H271 . 116.6 no C6 . C27 . H272 . 116.6 no C8 . C27 . H272 . 117.5 no H271 . C27 . H272 . 111.1 no C10 . N1 . C21 . 116.56(18) yes C10 . N1 . C16 . 115.16(18) yes C21 . N1 . C16 . 128.20(18) yes C6 . S1 . C5 . 103.84(10) yes C6 . S1 . O1 . 107.95(11) yes C5 . S1 . O1 . 109.69(11) yes C6 . S1 . O2 . 107.12(11) yes C5 . S1 . O2 . 108.40(12) yes O1 . S1 . O2 . 118.79(11) yes C12 . O4 . C11 . 114.56(19) yes C17 . O6 . C16 . 120.69(19) yes C102 . C101 . H1011 . 110.9 no C102 . C101 . H1012 . 108.6 no H1011 . C101 . H1012 . 109.2 no C102 . C101 . H1013 . 109.3 no H1011 . C101 . H1013 . 109.4 no H1012 . C101 . H1013 . 109.4 no C101 . C102 . C103 . 121.3(3) yes C101 . C102 . C113 . 120.1(4) yes C103 . C102 . C113 . 118.6(3) yes C102 . C103 . C104 . 122.0(3) yes C102 . C103 . H1031 . 119.7 no C104 . C103 . H1031 . 118.3 no C103 . C104 . C105 . 118.8(3) yes C103 . C104 . H1041 . 121.5 no C105 . C104 . H1041 . 119.7 no C104 . C105 . C114 . 120.5(3) yes C104 . C105 . S101 . 119.9(2) yes C114 . C105 . S101 . 119.6(2) yes C107 . C106 . C108 . 53.80(13) yes C107 . C106 . C115 . 88.53(18) yes C108 . C106 . C115 . 53.83(13) yes C107 . C106 . C127 . 88.80(18) yes C108 . C106 . C127 . 53.73(13) yes C115 . C106 . C127 . 88.61(18) yes C107 . C106 . S101 . 123.62(17) yes C108 . C106 . S101 . 177.11(16) yes C115 . C106 . S101 . 126.25(17) yes C127 . C106 . S101 . 128.69(17) yes C106 . C107 . C108 . 73.31(16) yes C106 . C107 . H1071 . 117.0 no C108 . C107 . H1071 . 116.7 no C106 . C107 . H1072 . 116.9 no C108 . C107 . H1072 . 117.8 no H1071 . C107 . H1072 . 110.8 no C121 . O108 . C122 . 119.86(18) yes C107 . C108 . C106 . 52.89(13) yes C107 . C108 . C109 . 125.04(19) yes C106 . C108 . C109 . 177.94(18) yes C107 . C108 . C115 . 87.14(18) yes C106 . C108 . C115 . 52.80(13) yes C109 . C108 . C115 . 128.2(2) yes C107 . C108 . C127 . 87.48(18) yes C106 . C108 . C127 . 52.79(13) yes C109 . C108 . C127 . 128.3(2) yes C115 . C108 . C127 . 87.19(17) yes C108 . C109 . C110 . 113.47(19) yes C108 . C109 . H1091 . 108.7 no C110 . C109 . H1091 . 110.2 no C108 . C109 . H1092 . 107.5 no C110 . C109 . H1092 . 106.6 no H1091 . C109 . H1092 . 110.3 no C109 . C110 . C111 . 110.90(19) yes C109 . C110 . N101 . 113.76(19) yes C111 . C110 . N101 . 112.7(2) yes C109 . C110 . H1101 . 106.7 no C111 . C110 . H1101 . 105.6 no N101 . C110 . H1101 . 106.6 no C110 . C111 . O103 . 123.5(2) yes C110 . C111 . O104 . 112.3(2) yes O103 . C111 . O104 . 124.1(2) yes O104 . C112 . H1121 . 107.9 no O104 . C112 . H1122 . 109.0 no H1121 . C112 . H1122 . 108.7 no O104 . C112 . H1123 . 109.4 no H1121 . C112 . H1123 . 110.6 no H1122 . C112 . H1123 . 111.2 no C102 . C113 . C114 . 120.6(3) yes C102 . C113 . H1131 . 120.4 no C114 . C113 . H1131 . 119.0 no C105 . C114 . C113 . 119.6(3) yes C105 . C114 . H1141 . 120.9 no C113 . C114 . H1141 . 119.5 no C106 . C115 . C108 . 73.37(16) yes C106 . C115 . H1151 . 117.4 no C108 . C115 . H1151 . 117.6 no C106 . C115 . H1152 . 117.8 no C108 . C115 . H1152 . 117.3 no H1151 . C115 . H1152 . 109.6 no N101 . C116 . O105 . 120.8(2) yes N101 . C116 . O106 . 112.0(2) yes O105 . C116 . O106 . 127.1(2) yes C118 . C117 . C119 . 110.8(3) yes C118 . C117 . C120 . 112.9(4) yes C119 . C117 . C120 . 110.7(3) yes C118 . C117 . O106 . 109.0(3) yes C119 . C117 . O106 . 102.2(2) yes C120 . C117 . O106 . 110.8(3) yes C117 . C118 . H1181 . 109.0 no C117 . C118 . H1182 . 107.9 no H1181 . C118 . H1182 . 109.7 no C117 . C118 . H1183 . 109.3 no H1181 . C118 . H1183 . 109.7 no H1182 . C118 . H1183 . 111.1 no C117 . C119 . H1191 . 109.2 no C117 . C119 . H1192 . 109.4 no H1191 . C119 . H1192 . 108.3 no C117 . C119 . H1193 . 110.7 no H1191 . C119 . H1193 . 108.9 no H1192 . C119 . H1193 . 110.3 no C117 . C120 . H1201 . 108.4 no C117 . C120 . H1202 . 108.1 no H1201 . C120 . H1202 . 111.0 no C117 . C120 . H1203 . 107.1 no H1201 . C120 . H1203 . 111.0 no H1202 . C120 . H1203 . 111.1 no O108 . C121 . N101 . 112.13(19) yes O108 . C121 . O107 . 126.5(2) yes N101 . C121 . O107 . 121.2(2) yes O108 . C122 . C123 . 110.22(19) yes O108 . C122 . C124 . 101.29(19) yes C123 . C122 . C124 . 111.1(2) yes O108 . C122 . C125 . 109.02(19) yes C123 . C122 . C125 . 113.7(2) yes C124 . C122 . C125 . 110.8(2) yes C122 . C123 . H1231 . 109.0 no C122 . C123 . H1232 . 110.5 no H1231 . C123 . H1232 . 109.0 no C122 . C123 . H1233 . 111.3 no H1231 . C123 . H1233 . 108.4 no H1232 . C123 . H1233 . 108.7 no C122 . C124 . H1241 . 109.9 no C122 . C124 . H1242 . 111.8 no H1241 . C124 . H1242 . 108.6 no C122 . C124 . H1243 . 109.2 no H1241 . C124 . H1243 . 108.8 no H1242 . C124 . H1243 . 108.5 no C122 . C125 . H1251 . 109.3 no C122 . C125 . H1252 . 110.5 no H1251 . C125 . H1252 . 108.9 no C122 . C125 . H1253 . 109.8 no H1251 . C125 . H1253 . 108.8 no H1252 . C125 . H1253 . 109.4 no C106 . C127 . C108 . 73.48(16) yes C106 . C127 . H1271 . 117.4 no C108 . C127 . H1271 . 115.7 no C106 . C127 . H1272 . 117.6 no C108 . C127 . H1272 . 116.9 no H1271 . C127 . H1272 . 111.3 no C110 . N101 . C121 . 115.60(18) yes C110 . N101 . C116 . 116.64(18) yes C121 . N101 . C116 . 126.89(19) yes C106 . S101 . C105 . 104.16(11) yes C106 . S101 . O101 . 108.16(12) yes C105 . S101 . O101 . 109.07(13) yes C106 . S101 . O102 . 106.96(11) yes C105 . S101 . O102 . 108.20(12) yes O101 . S101 . O102 . 119.25(13) yes C112 . O104 . C111 . 115.7(2) yes C117 . O106 . C116 . 121.1(2) yes Cl202 . C201 . Cl203 . 112.63(7) yes Cl202 . C201 . H2011 . 107.9 no Cl203 . C201 . H2011 . 108.6 no Cl202 . C201 . H2012 . 108.3 no Cl203 . C201 . H2012 . 108.9 no H2011 . C201 . H2012 . 110.5 no Cl212 . C211 . Cl213 . 112.65(7) yes Cl212 . C211 . H2111 . 110.1 no Cl213 . C211 . H2111 . 109.4 no Cl212 . C211 . H2112 . 106.2 no Cl213 . C211 . H2112 . 107.2 no H2111 . C211 . H2112 . 111.3 no Cl222 . C221 . Cl223 . 112.63(7) yes Cl222 . C221 . H2211 . 109.1 no Cl223 . C221 . H2211 . 108.0 no Cl222 . C221 . H2212 . 109.7 no Cl223 . C221 . H2212 . 107.9 no H2211 . C221 . H2212 . 109.5 no Cl232 . C231 . Cl233 . 112.66(7) yes Cl232 . C231 . H2311 . 108.5 no Cl233 . C231 . H2311 . 108.6 no Cl232 . C231 . H2312 . 108.8 no Cl233 . C231 . H2312 . 108.9 no H2311 . C231 . H2312 . 109.4 no Cl242 . C241 . Cl243 . 112.65(7) yes Cl242 . C241 . H2411 . 109.1 no Cl243 . C241 . H2411 . 108.0 no Cl242 . C241 . H2412 . 108.9 no Cl243 . C241 . H2412 . 108.7 no H2411 . C241 . H2412 . 109.4 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C4 . H41 . O107 2_656 171 0.93 2.27 3.196(6) yes C12 . H121 . O104 1_465 138 0.97 2.56 3.340(6) yes C12 . H121 . O107 1_465 128 0.97 2.53 3.217(6) yes C101 . H1013 . O2 . 145 0.95 2.55 3.370(6) yes C201 . H2012 . O105 . 163 0.95 2.44 3.362(6) yes C231 . H2012 . O105 . 151 0.77 2.44 3.141(6) yes C211 . H2111 . O5 1_655 135 0.98 2.34 3.107(6) yes C221 . H2111 . O5 1_655 122 1.12 2.34 3.085(6) yes C221 . H2211 . O5 1_655 165 0.97 2.13 3.085(6) yes C231 . H2312 . O105 . 162 0.97 2.21 3.141(6) yes C241 . H2411 . O5 1_655 160 0.97 2.08 3.010(6) yes C241 . H2412 . O105 . 148 0.97 2.52 3.377(6) yes _iucr_refine_instructions_details ; # # Punched on 08/09/22 at 02:41:25 # #LIST 12 BLOCK SCALE X'S U'S EQUIV PART(1001,OCC) EQUIV PART(1002,OCC) EQUIV PART(1003,OCC) EQUIV PART(1004,OCC) EQUIV PART(1005,OCC) RIDE C(201,U'S) C(231,U'S) RIDE C(211,U'S) C(221,U'S) RIDE C(241,U'S) CL(222,U'S) RIDE C ( 1,X'S) H ( 11,X'S) H ( 12,X'S) H ( 13,X'S) RIDE C ( 3,X'S) H ( 31,X'S) RIDE C ( 4,X'S) H ( 41,X'S) RIDE C ( 7,X'S) H ( 71,X'S) H ( 72,X'S) RIDE C ( 9,X'S) H ( 91,X'S) H ( 92,X'S) RIDE C ( 10,X'S) H ( 101,X'S) RIDE C ( 12,X'S) H ( 121,X'S) H ( 122,X'S) H ( 123,X'S) RIDE C ( 13,X'S) H ( 131,X'S) RIDE C ( 14,X'S) H ( 141,X'S) RIDE C ( 15,X'S) H ( 151,X'S) H ( 152,X'S) RIDE C ( 18,X'S) H ( 181,X'S) H ( 182,X'S) H ( 183,X'S) RIDE C ( 19,X'S) H ( 191,X'S) H ( 192,X'S) H ( 193,X'S) RIDE C ( 20,X'S) H ( 201,X'S) H ( 202,X'S) H ( 203,X'S) RIDE C ( 23,X'S) H ( 231,X'S) H ( 232,X'S) H ( 233,X'S) RIDE C ( 24,X'S) H ( 241,X'S) H ( 242,X'S) H ( 243,X'S) RIDE C ( 25,X'S) H ( 251,X'S) H ( 252,X'S) H ( 253,X'S) RIDE C ( 27,X'S) H ( 271,X'S) H ( 272,X'S) RIDE C ( 101,X'S) H (1011,X'S) H (1012,X'S) H (1013,X'S) RIDE C ( 103,X'S) H (1031,X'S) RIDE C ( 104,X'S) H (1041,X'S) RIDE C ( 107,X'S) H (1071,X'S) H (1072,X'S) RIDE C ( 109,X'S) H (1091,X'S) H (1092,X'S) RIDE C ( 110,X'S) H (1101,X'S) RIDE C ( 112,X'S) H (1121,X'S) H (1122,X'S) H (1123,X'S) RIDE C ( 113,X'S) H (1131,X'S) RIDE C ( 114,X'S) H (1141,X'S) RIDE C ( 115,X'S) H (1151,X'S) H (1152,X'S) RIDE C ( 118,X'S) H (1181,X'S) H (1182,X'S) H (1183,X'S) RIDE C ( 119,X'S) H (1191,X'S) H (1192,X'S) H (1193,X'S) RIDE C ( 120,X'S) H (1201,X'S) H (1202,X'S) H (1203,X'S) RIDE C ( 123,X'S) H (1231,X'S) H (1232,X'S) H (1233,X'S) RIDE C ( 124,X'S) H (1241,X'S) H (1242,X'S) H (1243,X'S) RIDE C ( 125,X'S) H (1251,X'S) H (1252,X'S) H (1253,X'S) RIDE C ( 127,X'S) H (1271,X'S) H (1272,X'S) RIDE C ( 201,X'S) H (2011,X'S) H (2012,X'S) RIDE C ( 211,X'S) H (2111,X'S) H (2112,X'S) RIDE C ( 221,X'S) H (2211,X'S) H (2212,X'S) RIDE C ( 231,X'S) H (2311,X'S) H (2312,X'S) RIDE C ( 241,X'S) H (2411,X'S) H (2412,X'S) END # # Punched on 08/09/22 at 02:41:25 # #LIST 16 SAME CONT C(201) CL(202) CL(203) AND CONT C(201) CL(202) CL(203) AND CONT C(211) CL(212) CL(213) AND CONT C(211) CL(213) CL(212) AND CONT C(221) CL(222) CL(223) AND CONT C(221) CL(223) CL(222) AND CONT C(231) CL(232) CL(233) AND CONT C(231) CL(232) CL(233) AND CONT C(241) CL(242) CL(243) AND CONT C(241) CL(242) CL(243) SIMU 0.01 CONT C(201) CL(202) CL(203) AND CONT C(201) CL(202) CL(203) AND CONT C(211) CL(212) CL(213) AND CONT C(211) CL(213) CL(212) AND CONT C(221) CL(222) CL(223) AND CONT C(221) CL(223) CL(222) AND CONT C(231) CL(232) CL(233) AND CONT C(231) CL(232) CL(233) AND CONT C(241) CL(242) CL(243) AND CONT C(241) CL(242) CL(243) DELU 0.01 CONT C(201) CL(202) CL(203) AND CONT C(201) CL(202) CL(203) AND CONT C(211) CL(212) CL(213) AND CONT C(211) CL(213) CL(212) AND CONT C(221) CL(222) CL(223) AND CONT C(221) CL(223) CL(222) AND CONT C(231) CL(232) CL(233) AND CONT C(231) CL(232) CL(233) AND CONT C(241) CL(242) CL(243) AND CONT C(241) CL(242) CL(243) LIMIT 0.01000000 C(211,X) LIMIT 0.01000000 C(211,Y) LIMIT 0.01000000 C(211,Z) LIMIT 0.01000000 C(241,X) LIMIT 0.01000000 C(241,Y) LIMIT 0.01000000 C(241,Z) REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; _refine_special_details ; On initial refinement, residual electron density was visible. Further examination suggested this was dichloromethane which refined, but with unlikely displacement ellipsoids. Further examination of the difference Fourier map suggested this was due to disorder. The final model included five components all partially occupied. The close location of all these meant restraints were necessary to ensure convergence and sensible geometrical parameters and displacements. Reflections are selected by the following conditions :- Minimum value of SQRTW is 0.00 Minimum value of RATIO is -3.00 ; #==============================================================================