#------------------------------------------------------------------------------ #$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $ #$Revision: 176798 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/23/41/2234111.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2234111 loop_ _publ_author_name 'Petrus, Joanna' 'Petrus, Rafa\/l' 'Czarnik-Matusewicz, Bogus\/lawa' _publ_section_title ; Fluphenazine dihydrochloride dimethanol solvate ; _journal_coeditor_code BT5828 _journal_issue 4 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1004 _journal_page_last o1005 _journal_paper_doi 10.1107/S1600536812008707 _journal_volume 68 _journal_year 2012 _chemical_formula_iupac 'C22 H28 F3 N3 O S 2+, 2Cl -, 2(C H4 O)' _chemical_formula_moiety 'C22 H28 F3 N3 O S 2+, 2(Cl -), 2(C H4 O)' _chemical_formula_sum 'C24 H36 Cl2 F3 N3 O3 S' _chemical_formula_weight 574.53 _chemical_name_common 'dihydrochloride fluphenazine dimethanol solvate' _chemical_name_systematic ; 1-(2-hydroxyethyl)-4-[3-(2-trifluoromethyl-10H-phenothiazin- 10-yl)propyl]piperazine-1,4-diium dichloride dimethanol disolvate ; _space_group_IT_number 29 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2ac' _symmetry_space_group_name_H-M 'P c a 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 39.76(2) _cell_length_b 9.952(8) _cell_length_c 7.127(5) _cell_measurement_reflns_used 13454 _cell_measurement_temperature 85(2) _cell_measurement_theta_max 38.5080 _cell_measurement_theta_min 4.8221 _cell_volume 2820(3) _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, 2007)' _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2007)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2007)' _computing_molecular_graphics 'XP in SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 85(2) _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.983 _diffrn_measurement_device_type ; Oxford Diffraction Xcalibur PX \k-geometry diffractometer with CCD Onyx camera ; _diffrn_measurement_method '\w and \f' _diffrn_radiation_monochromator graphite/ _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0521 _diffrn_reflns_av_sigmaI/netI 0.0758 _diffrn_reflns_limit_h_max 64 _diffrn_reflns_limit_h_min -69 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 43952 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 38.60 _diffrn_reflns_theta_min 4.83 _exptl_absorpt_coefficient_mu 0.354 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.85009 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (CrysAlis RED; Oxford Diffraction, 2007) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 1208 _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _refine_diff_density_max 1.249 _refine_diff_density_min -0.849 _refine_ls_abs_structure_details 'Flack (1983), 5579 Friedel pairs' _refine_ls_abs_structure_Flack 0.09(7) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.187 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 330 _refine_ls_number_reflns 13922 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.187 _refine_ls_R_factor_all 0.1095 _refine_ls_R_factor_gt 0.0836 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0620P)^2^+4.2740P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1891 _refine_ls_wR_factor_ref 0.1973 _reflns_number_gt 10615 _reflns_number_total 13922 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL JS1.INS in Pca21 CELL 0.71073 39.764 9.952 7.127 90.00 90.00 90.00 ZERR 4 0.020 0.008 0.005 0.00 0.00 0.00 LATT -1 SYMM - X , - Y , 0.50000 + Z SYMM 0.50000 - X , Y , 0.50000 + Z SYMM 0.50000 + X , - Y , Z SFAC C H Cl F N O S UNIT 96 144 8 12 12 12 4 L.S. 100 FMAP 2 PLAN -20 TEMP -188 ACTA 50 BOND $H EQIV $1 1-x, -y, -0.5+z EQIV $2 1-x, 1-y, -0.5+z EQIV $3 1.5-x,-1+y,-0.5+z EQIV $4 1-x, 1-y, -0.5+z EQIV $5 1-x, -y,0.5+z EQIV $6 1-x, -y, -0.5+z EQIV $7 x, y, -1+z EQIV $8 1-x, 1-y, -0.5+z HTAB N16 CL2 HTAB N18 CL1 HTAB O24 CL1 HTAB O22 CL2_$1 HTAB O23 CL2_$2 HTAB C18 O22 HTAB C21 O23 HTAB C2 F13A_$3 HTAB C14 O23_$4 HTAB C17 O24_$5 HTAB C17 O22_$6 HTAB C16 CL2_$7 HTAB C19 CL2_$8 CONF WGHT 0.062000 4.274000 FVAR 1.71813 S1 7 0.716794 0.159553 0.471967 11.00000 0.02095 0.01320 = 0.02550 0.00178 -0.00707 0.00155 C1 1 0.690588 0.162584 0.271997 11.00000 0.01365 0.00842 = 0.02030 0.00132 -0.00013 -0.00069 C2 1 0.695910 0.073345 0.124464 11.00000 0.01644 0.01054 = 0.02891 -0.00224 0.00353 0.00248 AFIX 43 H2 2 0.713947 0.010882 0.130130 11.00000 -1.20000 AFIX 0 C3 1 0.674892 0.075644 -0.030650 11.00000 0.02589 0.01614 = 0.02302 -0.00575 0.00318 0.00165 AFIX 43 H3 2 0.678129 0.013594 -0.130320 11.00000 -1.20000 AFIX 0 C4 1 0.649101 0.169243 -0.039195 11.00000 0.02569 0.02203 = 0.01753 -0.00266 -0.00467 0.00098 AFIX 43 H4 2 0.634718 0.170915 -0.145605 11.00000 -1.20000 AFIX 0 C5 1 0.643974 0.260360 0.104987 11.00000 0.01597 0.01701 = 0.02032 -0.00014 -0.00167 0.00280 AFIX 43 H5 2 0.626508 0.325140 0.095578 11.00000 -1.20000 AFIX 0 C6 1 0.664443 0.257097 0.264074 11.00000 0.01352 0.00609 = 0.01980 -0.00093 0.00229 -0.00073 N6 5 0.660340 0.346847 0.419060 11.00000 0.01285 0.01116 = 0.02232 -0.00452 0.00177 0.00033 C7 1 0.689815 0.412021 0.478824 11.00000 0.01615 0.01231 = 0.01525 -0.00187 -0.00088 0.00002 C8 1 0.691415 0.549719 0.510482 11.00000 0.01641 0.01103 = 0.02533 -0.00151 0.00003 -0.00009 AFIX 43 H8 2 0.672215 0.604454 0.489268 11.00000 -1.20000 AFIX 0 C9 1 0.721367 0.607112 0.573575 11.00000 0.02112 0.01432 = 0.02584 -0.00645 -0.00209 -0.00482 C10 1 0.750000 0.532173 0.598857 11.00000 0.01997 0.02050 = 0.02529 -0.00340 -0.00432 -0.00214 AFIX 43 H10 2 0.770228 0.573095 0.640861 11.00000 -1.20000 AFIX 0 C11 1 0.748765 0.395683 0.561831 11.00000 0.01807 0.01984 = 0.02462 -0.00195 -0.00575 0.00077 AFIX 43 H11 2 0.768587 0.343190 0.574625 11.00000 -1.20000 AFIX 0 C12 1 0.719116 0.334441 0.506466 11.00000 0.01628 0.01750 = 0.01843 -0.00038 -0.00411 0.00122 C13 1 0.721072 0.754871 0.614559 11.00000 0.02583 0.01916 = 0.04131 -0.00847 0.00137 -0.00616 F13A 4 0.751424 0.806782 0.635517 11.00000 0.02610 0.02341 = 0.11632 -0.02511 0.00140 -0.01066 F13B 4 0.704989 0.825972 0.484126 11.00000 0.06282 0.01251 = 0.06555 -0.00162 -0.01499 -0.00132 F13C 4 0.704601 0.782008 0.776082 11.00000 0.06626 0.02773 = 0.05606 -0.01796 0.02314 -0.00461 C14 1 0.628433 0.419132 0.433475 11.00000 0.01390 0.01711 = 0.02239 -0.00336 0.00349 0.00136 AFIX 23 H14A 2 0.624186 0.468371 0.315124 11.00000 -1.20000 H14B 2 0.629865 0.485768 0.536303 11.00000 -1.20000 AFIX 0 C15 1 0.599296 0.323134 0.471484 11.00000 0.01346 0.01218 = 0.02331 -0.00102 0.00364 0.00153 AFIX 23 H15A 2 0.599759 0.248179 0.380195 11.00000 -1.20000 H15B 2 0.601336 0.285025 0.599289 11.00000 -1.20000 AFIX 0 C16 1 0.566396 0.400322 0.453545 11.00000 0.01349 0.01101 = 0.01534 -0.00010 0.00246 0.00037 AFIX 23 H16A 2 0.569133 0.491013 0.508544 11.00000 -1.20000 H16B 2 0.560708 0.411112 0.319151 11.00000 -1.20000 AFIX 0 N16 5 0.538156 0.328118 0.552044 11.00000 0.01174 0.01140 = 0.01038 -0.00077 -0.00152 0.00111 AFIX 13 H16 2 0.543573 0.323825 0.678844 11.00000 -1.20000 AFIX 0 C17 1 0.533091 0.187204 0.484190 11.00000 0.01433 0.00953 = 0.01874 -0.00222 -0.00102 0.00090 AFIX 23 H17A 2 0.554134 0.135410 0.500929 11.00000 -1.20000 H17B 2 0.527551 0.188239 0.348772 11.00000 -1.20000 AFIX 0 C18 1 0.505163 0.120808 0.591129 11.00000 0.01614 0.00620 = 0.02158 -0.00144 -0.00222 0.00137 AFIX 23 H18A 2 0.502163 0.027827 0.544675 11.00000 -1.20000 H18B 2 0.511283 0.116037 0.725609 11.00000 -1.20000 AFIX 0 N18 5 0.472762 0.196096 0.570397 11.00000 0.01332 0.00720 = 0.01179 0.00063 -0.00082 0.00124 AFIX 13 H18 2 0.467648 0.201483 0.443288 11.00000 -1.20000 AFIX 0 C19 1 0.478082 0.336166 0.643037 11.00000 0.01551 0.00844 = 0.01560 -0.00113 0.00127 -0.00111 AFIX 23 H19A 2 0.483967 0.332738 0.777923 11.00000 -1.20000 H19B 2 0.457045 0.388498 0.629643 11.00000 -1.20000 AFIX 0 C20 1 0.506094 0.404445 0.534777 11.00000 0.01403 0.00368 = 0.01273 0.00112 -0.00017 0.00069 AFIX 23 H20A 2 0.499724 0.411081 0.400813 11.00000 -1.20000 H20B 2 0.509331 0.496702 0.583491 11.00000 -1.20000 AFIX 0 C21 1 0.443649 0.130946 0.669211 11.00000 0.01685 0.01258 = 0.01569 0.00085 0.00311 -0.00317 AFIX 23 H21A 2 0.425887 0.198964 0.690509 11.00000 -1.20000 H21B 2 0.451234 0.098114 0.793320 11.00000 -1.20000 AFIX 0 C22 1 0.429019 0.015152 0.560010 11.00000 0.02117 0.01182 = 0.01786 0.00156 0.00082 -0.00333 AFIX 23 H22A 2 0.409371 -0.022022 0.627717 11.00000 -1.20000 H22B 2 0.421356 0.046795 0.435450 11.00000 -1.20000 AFIX 0 O22 6 0.453822 -0.085989 0.537552 11.00000 0.02634 0.01196 = 0.04037 -0.00597 0.00138 -0.00387 AFIX 147 H22 2 0.444483 -0.161610 0.532432 11.00000 -1.50000 AFIX 0 O23 6 0.391796 0.372541 0.557590 11.00000 0.03749 0.02285 = 0.03944 0.00335 -0.00431 -0.00377 AFIX 147 H23 2 0.400058 0.445130 0.518961 11.00000 -1.50000 AFIX 0 C23 1 0.363110 0.341030 0.451490 11.00000 0.08013 0.05522 = 0.07743 0.01319 -0.03800 -0.03591 AFIX 137 H23A 2 0.348439 0.419979 0.444145 11.00000 -1.50000 H23B 2 0.350964 0.266918 0.511531 11.00000 -1.50000 H23C 2 0.369905 0.314200 0.324735 11.00000 -1.50000 AFIX 0 O24 6 0.406556 0.021423 0.056280 11.00000 0.01895 0.01567 = 0.03534 -0.00409 0.00124 -0.00206 AFIX 147 H24 2 0.418955 0.087463 0.080813 11.00000 -1.50000 AFIX 0 C24 1 0.373209 0.067474 0.018072 11.00000 0.01753 0.04471 = 0.03826 -0.00690 0.00146 0.00277 AFIX 137 H24A 2 0.363901 0.110123 0.130609 11.00000 -1.50000 H24B 2 0.359066 -0.008956 -0.017864 11.00000 -1.50000 H24C 2 0.373791 0.132831 -0.084728 11.00000 -1.50000 AFIX 0 CL1 3 0.459485 0.246521 0.150779 11.00000 0.02536 0.01817 = 0.01180 0.00166 -0.00409 -0.00555 CL2 3 0.562033 0.380321 0.947117 11.00000 0.02121 0.01314 = 0.01291 -0.00118 -0.00343 0.00215 HKLF 4 1 0.0000 0.0000 -1.0000 0.0000 -1.0000 0.0000 -1.0000 0.0000 0.0000 REM JS1.INS in Pca21 REM R1 = 0.0836 for 10615 Fo > 4sig(Fo) and 0.1095 for all 13922 data REM 330 parameters refined using 1 restraints END WGHT 0.0620 4.2739 REM Highest difference peak 1.249, deepest hole -0.849, 1-sigma level 0.125 Q1 1 0.4594 0.3213 0.1549 11.00000 0.05 1.25 Q2 1 0.4558 0.1627 0.1560 11.00000 0.05 0.99 Q3 1 0.7174 0.2411 0.4827 11.00000 0.05 0.89 Q4 1 0.4371 -0.4654 0.4434 11.00000 0.05 0.88 Q5 1 0.7043 0.8991 0.4856 11.00000 0.05 0.75 Q6 1 0.4491 -0.2808 0.4833 11.00000 0.05 0.72 Q7 1 0.4703 0.2669 0.5980 11.00000 0.05 0.65 Q8 1 0.7112 0.0561 0.4716 11.00000 0.05 0.63 Q9 1 0.6907 0.4819 0.4888 11.00000 0.05 0.63 Q10 1 0.5051 0.4873 0.5377 11.00000 0.05 0.59 Q11 1 0.4486 -0.0649 0.4426 11.00000 0.05 0.57 Q12 1 0.4714 0.1644 0.1534 11.00000 0.05 0.56 Q13 1 0.5088 0.3142 0.5287 11.00000 0.05 0.56 Q14 1 0.7233 0.6840 0.5783 11.00000 0.05 0.55 Q15 1 0.3917 0.2868 0.5398 11.00000 0.05 0.54 Q16 1 0.7084 0.3943 0.4892 11.00000 0.05 0.53 Q17 1 0.6894 0.6384 0.5136 11.00000 0.05 0.51 Q18 1 0.6983 0.3226 0.4659 11.00000 0.05 0.50 Q19 1 0.4829 0.2920 0.1894 11.00000 0.05 0.50 Q20 1 0.4644 0.0429 0.1499 11.00000 0.05 0.50 ; _cod_data_source_file bt5828.cif _cod_data_source_block I _cod_database_code 2234111 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_symmetry_multiplicity S S1 0.716794(19) 0.15955(8) 0.47197(13) 0.01988(15) Uani d . 1 1 C C1 0.69059(7) 0.1626(3) 0.2720(4) 0.0141(5) Uani d . 1 1 C C2 0.69591(8) 0.0733(3) 0.1245(5) 0.0186(6) Uani d . 1 1 H H2 0.7139 0.0109 0.1301 0.022 Uiso calc R 1 1 C C3 0.67489(8) 0.0756(3) -0.0306(5) 0.0217(6) Uani d . 1 1 H H3 0.6781 0.0136 -0.1303 0.026 Uiso calc R 1 1 C C4 0.64910(8) 0.1692(3) -0.0392(5) 0.0218(5) Uani d . 1 1 H H4 0.6347 0.1709 -0.1456 0.026 Uiso calc R 1 1 C C5 0.64397(7) 0.2604(3) 0.1050(5) 0.0178(5) Uani d . 1 1 H H5 0.6265 0.3251 0.0956 0.021 Uiso calc R 1 1 C C6 0.66444(7) 0.2571(3) 0.2641(4) 0.0131(4) Uani d . 1 1 N N6 0.66034(6) 0.3468(2) 0.4191(4) 0.0154(5) Uani d . 1 1 C C7 0.68982(7) 0.4120(3) 0.4788(4) 0.0146(5) Uani d . 1 1 C C8 0.69142(8) 0.5497(3) 0.5105(5) 0.0176(5) Uani d . 1 1 H H8 0.6722 0.6045 0.4893 0.021 Uiso calc R 1 1 C C9 0.72137(8) 0.6071(3) 0.5736(5) 0.0204(6) Uani d . 1 1 C C10 0.75000(9) 0.5322(3) 0.5989(5) 0.0219(6) Uani d . 1 1 H H10 0.7702 0.5731 0.6409 0.026 Uiso calc R 1 1 C C11 0.74876(8) 0.3957(3) 0.5618(5) 0.0208(6) Uani d . 1 1 H H11 0.7686 0.3432 0.5746 0.025 Uiso calc R 1 1 C C12 0.71912(7) 0.3344(3) 0.5065(4) 0.0174(5) Uani d . 1 1 C C13 0.72107(9) 0.7549(4) 0.6146(6) 0.0288(8) Uani d . 1 1 F F13A 0.75142(7) 0.8068(2) 0.6355(6) 0.0553(10) Uani d . 1 1 F F13B 0.70499(8) 0.8260(2) 0.4841(5) 0.0470(7) Uani d . 1 1 F F13C 0.70460(9) 0.7820(3) 0.7761(5) 0.0500(8) Uani d . 1 1 C C14 0.62843(7) 0.4191(3) 0.4335(5) 0.0178(5) Uani d . 1 1 H H14A 0.6242 0.4684 0.3151 0.021 Uiso calc R 1 1 H H14B 0.6299 0.4858 0.5363 0.021 Uiso calc R 1 1 C C15 0.59930(7) 0.3231(3) 0.4715(5) 0.0163(5) Uani d . 1 1 H H15A 0.5998 0.2482 0.3802 0.020 Uiso calc R 1 1 H H15B 0.6013 0.2850 0.5993 0.020 Uiso calc R 1 1 C C16 0.56640(6) 0.4003(2) 0.4535(5) 0.0133(4) Uani d . 1 1 H H16A 0.5691 0.4910 0.5085 0.016 Uiso calc R 1 1 H H16B 0.5607 0.4111 0.3192 0.016 Uiso calc R 1 1 N N16 0.53816(6) 0.3281(2) 0.5520(3) 0.0112(4) Uani d . 1 1 H H16 0.5436 0.3238 0.6788 0.013 Uiso calc R 1 1 C C17 0.53309(7) 0.1872(3) 0.4842(4) 0.0142(5) Uani d . 1 1 H H17A 0.5541 0.1354 0.5009 0.017 Uiso calc R 1 1 H H17B 0.5276 0.1882 0.3488 0.017 Uiso calc R 1 1 C C18 0.50516(7) 0.1208(3) 0.5911(5) 0.0146(5) Uani d . 1 1 H H18A 0.5022 0.0278 0.5447 0.018 Uiso calc R 1 1 H H18B 0.5113 0.1160 0.7256 0.018 Uiso calc R 1 1 N N18 0.47276(6) 0.1961(2) 0.5704(3) 0.0108(4) Uani d . 1 1 H H18 0.4676 0.2015 0.4433 0.013 Uiso calc R 1 1 C C19 0.47808(7) 0.3362(3) 0.6430(4) 0.0132(4) Uani d . 1 1 H H19A 0.4840 0.3327 0.7779 0.016 Uiso calc R 1 1 H H19B 0.4570 0.3885 0.6296 0.016 Uiso calc R 1 1 C C20 0.50609(6) 0.4044(2) 0.5348(4) 0.0101(4) Uani d . 1 1 H H20A 0.4997 0.4111 0.4008 0.012 Uiso calc R 1 1 H H20B 0.5093 0.4967 0.5835 0.012 Uiso calc R 1 1 C C21 0.44365(7) 0.1309(3) 0.6692(4) 0.0150(5) Uani d . 1 1 H H21A 0.4259 0.1990 0.6905 0.018 Uiso calc R 1 1 H H21B 0.4512 0.0981 0.7933 0.018 Uiso calc R 1 1 C C22 0.42902(8) 0.0152(3) 0.5600(5) 0.0170(5) Uani d . 1 1 H H22A 0.4094 -0.0220 0.6277 0.020 Uiso calc R 1 1 H H22B 0.4214 0.0468 0.4355 0.020 Uiso calc R 1 1 O O22 0.45382(7) -0.0860(2) 0.5376(4) 0.0262(5) Uani d . 1 1 H H22 0.4445 -0.1616 0.5324 0.039 Uiso calc R 1 1 O O23 0.39180(8) 0.3725(3) 0.5576(5) 0.0333(6) Uani d . 1 1 H H23 0.4001 0.4451 0.5190 0.050 Uiso calc R 1 1 C C23 0.36311(18) 0.3410(7) 0.4515(13) 0.071(2) Uani d . 1 1 H H23A 0.3484 0.4200 0.4441 0.106 Uiso calc R 1 1 H H23B 0.3510 0.2669 0.5115 0.106 Uiso calc R 1 1 H H23C 0.3699 0.3142 0.3247 0.106 Uiso calc R 1 1 O O24 0.40656(6) 0.0214(2) 0.0563(4) 0.0233(5) Uani d . 1 1 H H24 0.4190 0.0875 0.0808 0.035 Uiso calc R 1 1 C C24 0.37321(9) 0.0675(5) 0.0181(6) 0.0335(9) Uani d . 1 1 H H24A 0.3639 0.1101 0.1306 0.050 Uiso calc R 1 1 H H24B 0.3591 -0.0090 -0.0179 0.050 Uiso calc R 1 1 H H24C 0.3738 0.1328 -0.0847 0.050 Uiso calc R 1 1 Cl Cl1 0.459485(19) 0.24652(8) 0.15078(11) 0.01844(13) Uani d . 1 1 Cl Cl2 0.562033(17) 0.38032(7) 0.94712(10) 0.01575(12) Uani d . 1 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 0.0209(3) 0.0132(3) 0.0255(4) 0.0016(2) -0.0071(3) 0.0018(3) C1 0.0136(11) 0.0084(10) 0.0203(13) -0.0007(9) -0.0001(9) 0.0013(9) C2 0.0164(11) 0.0105(11) 0.0289(17) 0.0025(9) 0.0035(11) -0.0022(10) C3 0.0259(13) 0.0161(12) 0.0230(15) 0.0017(10) 0.0032(13) -0.0057(12) C4 0.0257(13) 0.0220(13) 0.0175(13) 0.0010(11) -0.0047(12) -0.0027(13) C5 0.0160(12) 0.0170(12) 0.0203(14) 0.0028(10) -0.0017(10) -0.0001(10) C6 0.0135(10) 0.0061(9) 0.0198(13) -0.0007(8) 0.0023(9) -0.0009(9) N6 0.0128(9) 0.0112(9) 0.0223(13) 0.0003(8) 0.0018(8) -0.0045(8) C7 0.0162(10) 0.0123(10) 0.0153(12) 0.0000(8) -0.0009(9) -0.0019(9) C8 0.0164(11) 0.0110(11) 0.0253(15) -0.0001(9) 0.0000(10) -0.0015(10) C9 0.0211(13) 0.0143(12) 0.0258(15) -0.0048(10) -0.0021(12) -0.0064(11) C10 0.0200(13) 0.0205(14) 0.0253(16) -0.0021(11) -0.0043(12) -0.0034(12) C11 0.0181(12) 0.0198(14) 0.0246(15) 0.0008(10) -0.0057(11) -0.0019(12) C12 0.0163(11) 0.0175(12) 0.0184(14) 0.0012(10) -0.0041(10) -0.0004(10) C13 0.0258(15) 0.0192(15) 0.041(2) -0.0062(12) 0.0014(14) -0.0085(15) F13A 0.0261(11) 0.0234(11) 0.116(3) -0.0107(10) 0.0014(16) -0.0251(15) F13B 0.0628(17) 0.0125(9) 0.066(2) -0.0013(10) -0.0150(16) -0.0016(11) F13C 0.066(2) 0.0277(13) 0.0561(19) -0.0046(13) 0.0231(16) -0.0180(13) C14 0.0139(10) 0.0171(12) 0.0224(14) 0.0014(9) 0.0035(11) -0.0034(11) C15 0.0135(10) 0.0122(10) 0.0233(14) 0.0015(8) 0.0036(10) -0.0010(11) C16 0.0135(10) 0.0110(10) 0.0153(11) 0.0004(7) 0.0025(10) -0.0001(10) N16 0.0117(9) 0.0114(9) 0.0104(9) 0.0011(7) -0.0015(7) -0.0008(8) C17 0.0143(10) 0.0095(10) 0.0187(13) 0.0009(8) -0.0010(9) -0.0022(9) C18 0.0161(11) 0.0062(9) 0.0216(13) 0.0014(8) -0.0022(10) -0.0014(9) N18 0.0133(9) 0.0072(8) 0.0118(10) 0.0012(7) -0.0008(8) 0.0006(7) C19 0.0155(10) 0.0084(9) 0.0156(11) -0.0011(8) 0.0013(9) -0.0011(9) C20 0.0140(10) 0.0037(9) 0.0127(11) 0.0007(7) -0.0002(8) 0.0011(7) C21 0.0168(11) 0.0126(11) 0.0157(12) -0.0032(9) 0.0031(9) 0.0008(9) C22 0.0212(12) 0.0118(11) 0.0179(13) -0.0033(9) 0.0008(10) 0.0016(10) O22 0.0263(11) 0.0120(9) 0.0404(15) -0.0039(8) 0.0014(11) -0.0060(10) O23 0.0375(15) 0.0228(13) 0.0394(17) -0.0038(11) -0.0043(13) 0.0034(12) C23 0.080(4) 0.055(3) 0.077(4) -0.036(3) -0.038(4) 0.013(3) O24 0.0189(10) 0.0157(10) 0.0353(14) -0.0021(8) 0.0012(10) -0.0041(10) C24 0.0175(14) 0.045(2) 0.038(2) 0.0028(15) 0.0015(14) -0.0069(17) Cl1 0.0254(3) 0.0182(3) 0.0118(2) -0.0055(3) -0.0041(3) 0.0017(2) Cl2 0.0212(3) 0.0131(2) 0.0129(3) 0.0022(2) -0.0034(2) -0.0012(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C12 S1 C1 97.29(14) C2 C1 C6 120.6(3) C2 C1 S1 120.6(2) C6 C1 S1 118.8(2) C3 C2 C1 120.0(3) C3 C2 H2 120.0 C1 C2 H2 120.0 C2 C3 C4 119.5(3) C2 C3 H3 120.3 C4 C3 H3 120.3 C5 C4 C3 121.1(3) C5 C4 H4 119.5 C3 C4 H4 119.5 C4 C5 C6 120.1(3) C4 C5 H5 120.0 C6 C5 H5 120.0 C5 C6 C1 118.7(3) C5 C6 N6 123.1(3) C1 C6 N6 118.2(3) C7 N6 C6 115.3(2) C7 N6 C14 118.4(2) C6 N6 C14 117.4(2) C8 C7 N6 122.8(3) C8 C7 C12 118.6(3) N6 C7 C12 118.6(3) C7 C8 C9 119.7(3) C7 C8 H8 120.2 C9 C8 H8 120.2 C10 C9 C8 121.9(3) C10 C9 C13 120.9(3) C8 C9 C13 117.2(3) C9 C10 C11 118.6(3) C9 C10 H10 120.7 C11 C10 H10 120.7 C12 C11 C10 121.1(3) C12 C11 H11 119.5 C10 C11 H11 119.5 C11 C12 C7 120.1(3) C11 C12 S1 121.3(2) C7 C12 S1 118.6(2) F13A C13 F13B 108.0(4) F13A C13 F13C 105.6(3) F13B C13 F13C 104.8(3) F13A C13 C9 113.5(3) F13B C13 C9 112.9(3) F13C C13 C9 111.4(3) N6 C14 C15 111.3(2) N6 C14 H14A 109.4 C15 C14 H14A 109.4 N6 C14 H14B 109.4 C15 C14 H14B 109.4 H14A C14 H14B 108.0 C16 C15 C14 108.8(2) C16 C15 H15A 109.9 C14 C15 H15A 109.9 C16 C15 H15B 109.9 C14 C15 H15B 109.9 H15A C15 H15B 108.3 N16 C16 C15 111.1(2) N16 C16 H16A 109.4 C15 C16 H16A 109.4 N16 C16 H16B 109.4 C15 C16 H16B 109.4 H16A C16 H16B 108.0 C20 N16 C17 109.6(2) C20 N16 C16 110.9(2) C17 N16 C16 113.4(2) C20 N16 H16 107.6 C17 N16 H16 107.6 C16 N16 H16 107.6 N16 C17 C18 110.4(2) N16 C17 H17A 109.6 C18 C17 H17A 109.6 N16 C17 H17B 109.6 C18 C17 H17B 109.6 H17A C17 H17B 108.1 N18 C18 C17 111.5(2) N18 C18 H18A 109.3 C17 C18 H18A 109.3 N18 C18 H18B 109.3 C17 C18 H18B 109.3 H18A C18 H18B 108.0 C18 N18 C19 108.0(2) C18 N18 C21 113.6(2) C19 N18 C21 110.3(2) C18 N18 H18 108.2 C19 N18 H18 108.2 C21 N18 H18 108.2 N18 C19 C20 110.1(2) N18 C19 H19A 109.6 C20 C19 H19A 109.6 N18 C19 H19B 109.6 C20 C19 H19B 109.6 H19A C19 H19B 108.1 N16 C20 C19 111.0(2) N16 C20 H20A 109.4 C19 C20 H20A 109.4 N16 C20 H20B 109.4 C19 C20 H20B 109.4 H20A C20 H20B 108.0 N18 C21 C22 112.7(2) N18 C21 H21A 109.1 C22 C21 H21A 109.1 N18 C21 H21B 109.1 C22 C21 H21B 109.1 H21A C21 H21B 107.8 O22 C22 C21 109.4(3) O22 C22 H22A 109.8 C21 C22 H22A 109.8 O22 C22 H22B 109.8 C21 C22 H22B 109.8 H22A C22 H22B 108.2 C22 O22 H22 109.5 C23 O23 H23 109.5 O23 C23 H23A 109.5 O23 C23 H23B 109.5 H23A C23 H23B 109.5 O23 C23 H23C 109.5 H23A C23 H23C 109.5 H23B C23 H23C 109.5 C24 O24 H24 109.5 O24 C24 H24A 109.5 O24 C24 H24B 109.5 H24A C24 H24B 109.5 O24 C24 H24C 109.5 H24A C24 H24C 109.5 H24B C24 H24C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C12 1.760(4) S1 C1 1.766(3) C1 C2 1.393(4) C1 C6 1.403(4) C2 C3 1.386(5) C2 H2 0.9500 C3 C4 1.387(4) C3 H3 0.9500 C4 C5 1.386(5) C4 H4 0.9500 C5 C6 1.396(4) C5 H5 0.9500 C6 N6 1.430(4) N6 C7 1.406(4) N6 C14 1.462(4) C7 C8 1.390(4) C7 C12 1.412(4) C8 C9 1.395(4) C8 H8 0.9500 C9 C10 1.373(5) C9 C13 1.499(5) C10 C11 1.385(5) C10 H10 0.9500 C11 C12 1.385(4) C11 H11 0.9500 C13 F13A 1.321(4) C13 F13B 1.332(5) C13 F13C 1.352(5) C14 C15 1.526(4) C14 H14A 0.9900 C14 H14B 0.9900 C15 C16 1.522(4) C15 H15A 0.9900 C15 H15B 0.9900 C16 N16 1.507(4) C16 H16A 0.9900 C16 H16B 0.9900 N16 C20 1.489(3) N16 C17 1.497(4) N16 H16 0.9300 C17 C18 1.500(4) C17 H17A 0.9900 C17 H17B 0.9900 C18 N18 1.498(4) C18 H18A 0.9900 C18 H18B 0.9900 N18 C19 1.502(4) N18 C21 1.502(4) N18 H18 0.9300 C19 C20 1.516(4) C19 H19A 0.9900 C19 H19B 0.9900 C20 H20A 0.9900 C20 H20B 0.9900 C21 C22 1.507(4) C21 H21A 0.9900 C21 H21B 0.9900 C22 O22 1.418(4) C22 H22A 0.9900 C22 H22B 0.9900 O22 H22 0.8400 O23 C23 1.404(7) O23 H23 0.8400 C23 H23A 0.9800 C23 H23B 0.9800 C23 H23C 0.9800 O24 C24 1.429(4) O24 H24 0.8400 C24 H24A 0.9800 C24 H24B 0.9800 C24 H24C 0.9800 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N16 H16 Cl2 . 0.93 2.12 3.017(3) 160.5 N18 H18 Cl1 . 0.93 2.16 3.078(3) 170.5 O24 H24 Cl1 . 0.84 2.31 3.147(3) 171.5 O22 H22 Cl2 2_654 0.84 2.27 3.065(3) 156.8 O23 H23 Cl2 2_664 0.84 2.36 3.169(3) 162.8 C18 H18A O22 . 0.99 2.23 2.924(4) 125.9 C21 H21A O23 . 0.99 2.39 3.266(5) 146.9 C2 H2 F13A 3_644 0.95 2.45 3.381(4) 165.0 C14 H14A O23 2_664 0.99 2.51 3.482(5) 168.5 C17 H17A O24 2_655 0.99 2.24 3.215(4) 166.4 C17 H17B O22 2_654 0.99 2.55 3.379(5) 141.2 C16 H16B Cl2 1_554 0.99 2.67 3.619(4) 160.7 C19 H19B Cl2 2_664 0.99 2.75 3.529(3) 136.0 loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion C12 S1 C1 C2 141.0(3) C12 S1 C1 C6 -38.6(3) C6 C1 C2 C3 -1.2(4) S1 C1 C2 C3 179.2(2) C1 C2 C3 C4 1.4(5) C2 C3 C4 C5 -0.1(5) C3 C4 C5 C6 -1.4(5) C4 C5 C6 C1 1.6(4) C4 C5 C6 N6 -179.2(3) C2 C1 C6 C5 -0.3(4) S1 C1 C6 C5 179.3(2) C2 C1 C6 N6 -179.5(3) S1 C1 C6 N6 0.1(4) C5 C6 N6 C7 -130.1(3) C1 C6 N6 C7 49.0(4) C5 C6 N6 C14 16.7(4) C1 C6 N6 C14 -164.1(3) C6 N6 C7 C8 131.6(3) C14 N6 C7 C8 -14.9(5) C6 N6 C7 C12 -47.9(4) C14 N6 C7 C12 165.6(3) N6 C7 C8 C9 178.6(3) C12 C7 C8 C9 -1.9(5) C7 C8 C9 C10 2.6(5) C7 C8 C9 C13 -177.0(3) C8 C9 C10 C11 -0.6(6) C13 C9 C10 C11 179.0(3) C9 C10 C11 C12 -2.1(6) C10 C11 C12 C7 2.8(5) C10 C11 C12 S1 -176.4(3) C8 C7 C12 C11 -0.7(5) N6 C7 C12 C11 178.8(3) C8 C7 C12 S1 178.4(2) N6 C7 C12 S1 -2.0(4) C1 S1 C12 C11 -141.1(3) C1 S1 C12 C7 39.8(3) C10 C9 C13 F13A 13.7(6) C8 C9 C13 F13A -166.8(4) C10 C9 C13 F13B 137.1(4) C8 C9 C13 F13B -43.4(5) C10 C9 C13 F13C -105.3(4) C8 C9 C13 F13C 74.2(5) C7 N6 C14 C15 -148.0(3) C6 N6 C14 C15 66.1(4) N6 C14 C15 C16 -170.9(3) C14 C15 C16 N16 -160.3(3) C15 C16 N16 C20 179.7(2) C15 C16 N16 C17 -56.5(3) C20 N16 C17 C18 -56.8(3) C16 N16 C17 C18 178.8(2) N16 C17 C18 N18 59.1(3) C17 C18 N18 C19 -59.3(3) C17 C18 N18 C21 177.9(2) C18 N18 C19 C20 58.7(3) C21 N18 C19 C20 -176.6(2) C17 N16 C20 C19 57.3(3) C16 N16 C20 C19 -176.8(2) N18 C19 C20 N16 -59.3(3) C18 N18 C21 C22 -79.5(3) C19 N18 C21 C22 159.0(2) N18 C21 C22 O22 61.8(3)