data_global #============================================================================== # 1. SUBMISSION DETAILS #============================================================================== _publ_contact_author_name 'Dr Fran\,cois Brisse' _publ_contact_author_address ; Universit\'e de Montr\'eal D\'epartement de Chimie C.P. 6128, Succ. Centre-ville Montr\'eal, Qu\'ebec Canada, H3C 3J7 ; _publ_contact_author_phone '+1 514 343 2088' _publ_contact_author_fax '+1 514 343 7586' _publ_contact_author_email 'francois.brisse@umontreal.ca' _publ_requested_journal 'Acta Crystallographica C' _publ_requested_category 'FO' _publ_requested_coeditor_name ; Dr Anthony Linden Institute of Organic Chemistry University of Zurich Winterthurerstrasse 190 CH-8057 Zurich, Switzerland ; _publ_contact_letter ; Please consider this CIF submission for publication in Acta Crystallographica Section C. All authors have seen and approved of this submission. The CIF has passed the Chester CHECKCIF routines and gives a satisfactory PRINTCIF file. When I hear back from you by e-mail with your reference number I will fax and air-mail a formal Letter of Submission and a signed Copyright Transfer Form. I will then ftp the Artwork and Structure Factor Listing to you (as Postscript and ASCII files respectively). ; #============================================================================== # 2. PROCESSING SUMMARY (IUCr Office Use Only) #============================================================================== _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #============================================================================== # 3. TITLE AND AUTHOR LIST #============================================================================== _publ_section_title ; Structure of Complex 5 ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'Brisse, Fran\,cois' ; D\'epartement de Chimie Universit\'e de Montr\'eal C.P. 6128, Succ. Centre-ville, Montr\'eal, Qu\'ebec Canada H3C 3J7 ; 'Mohamed Osman, Awaleh' ; D\'epartement de Chimie Universit\'e de Montr\'eal C.P. 6128, Succ. Centre-ville, Montr\'eal, Qu\'ebec Canada H3C 3J7 ; 'Antonnella, Badia' ; D\'epartement de Chimie Universit\'e de Montr\'eal C.P. 6128, Succ. Centre-ville, Montr\'eal, Qu\'ebec Canada H3C 3J7 ; #============================================================================== # 4. TEXT #============================================================================== _publ_section_abstract ; Here should be written a short abstract ; _publ_section_comment ; Here should be written the text of the article ; _publ_section_exptl_prep ; Small details about the preparation of the compound. ; _publ_section_exptl_refinement ; All non-H atoms were refined by full-matrix least-squares with anisotropic displacement parameters. The H atoms were generated geometrically (C-H 0.96 to 0.97\%A) and were included in the refinement in the riding model approximation; their temperature factors were set to 1.5 times those of the equivalent isotropic temperature factors of the parent site (methyl) and 1.2 times for others. A final verification of possible voids was performed using the VOID routine of the PLATON program (Spek, 2000). ; _publ_section_references ; Bruker (1997). SHELXTL (1997). Release 5.10; The Complete Software Package for Single Crystal Structure Determination. Bruker AXS Inc., Madison, USA. Bruker (1999a). SAINT Release 6.06. Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, USA. Bruker (1999b). SMART Release 5.059; Bruker Molecular Analysis Research Tool, Bruker AXS Inc., Madison, USA. Flack, H. D. (1983). Acta Cryst. A39, 876-881. Flack, H. D. and Schwarzenbach, D. (1988). Acta Cryst. A44, 499-506. Sheldrick, G. M. (1986). SHELXS86. Program for Crystal Structure solution. University of G\"ottingen, Germany. Sheldrick, G. M. (1996). SADABS, Bruker Area Detector Absorption Corrections. Bruker AXS Inc., Madison, USA. Sheldrick, G. M. (1997a). SHELXS97. Program for Crystal Structure solution. University of G\"ottingen, Germany. Sheldrick, G. M. (1997b). SHELXL97. Program for crystal structure refinement. University of G\"ottingen, Germany. Spek, A. L. (2000). PLATON, 2000 version; Molecular Geometry Program, University of Utrecht, Utrecht, Holland. ; _publ_section_figure_captions ; Fig 1 Ortep view of the title compound. Thermal ellipsoids are shown at 30% probability levels. ; _publ_section_table_legends ; Table 1. Selected geometric parameters (\%A, \%) for the title compound. ; _publ_section_acknowledgements ; We are grateful to the Natural Sciences and Engineering Research Council of Canada and the Minist\`ere de l'Education du Qu\'ebec for financial support. ; # ======================================================== # STRUCTURAL DATA # ======================================================== data_complex5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C5 H8 Ag F3 O2 S2' _chemical_formula_sum 'C5 H8 Ag F3 O2 S2' _chemical_formula_weight 329.10 _chemical_compound_source 'Synthesized by the authors. See text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ag' 'Ag' 0.1306 4.2820 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pca21 _symmetry_space_group_name_hall 'P 2c -2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 10.4756(2) _cell_length_b 10.8952(2) _cell_length_c 8.90670(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1016.56(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6781 _cell_measurement_theta_min 4.06 _cell_measurement_theta_max 72.92 _exptl_crystal_description block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.150 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 19.948 _exptl_absorpt_correction_Type multi-scan _exptl_absorpt_correction_T_min 0.106 _exptl_absorpt_correction_T_max 0.204 _exptl_absorpt_process_details 'Sadabs (Sheldrick,1996)' _exptl_special_details ; X-ray crystallographic data for I were collected from a single crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Platform diffractometer, equipped with a Bruker SMART 2K Charged-Coupled Device (CCD) Area Detector using the program SMART and normal focus sealed tube source graphite monochromated Cu-K\a radiation. The crystal-to-detector distance was 4.908 cm, and the data collection was carried out in 512 x 512 pixel mode, utilizing 4 x 4 pixel binning. The initial unit cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 9.0 degree scan in 30 frames over four different parts of the reciprocal space (120 frames total). One complete sphere of data was collected, to better than 0.8\%A resolution. Upon completion of the data collection, the first 101 frames were recollected in order to improve the decay correction analysis. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'X-ray Sealed Tube' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device_type 'Bruker Smart 2000' _diffrn_measurement_method '\w' _diffrn_detector_area_resol_mean 5.5 _diffrn_standards_number 98 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% -0.31 _diffrn_reflns_number 8248 _diffrn_reflns_av_R_equivalents 0.084 _diffrn_reflns_av_sigmaI/netI 0.0504 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 4.06 _diffrn_reflns_theta_max 72.91 _reflns_number_total 1691 _reflns_number_gt 1616 _reflns_threshold_expression 'I>2\s(I)' _computing_data_collection 'SMART (Bruker, 1999)' _computing_cell_refinement 'SMART (Bruker, 1999)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'UdMX (local program)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1251P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), XXXX Friedel Pairs' _refine_ls_abs_structure_Flack 0.06(3) _refine_ls_number_reflns 1691 _refine_ls_number_parameters 118 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0695 _refine_ls_R_factor_gt 0.0682 _refine_ls_wR_factor_ref 0.1607 _refine_ls_wR_factor_gt 0.1595 _refine_ls_goodness_of_fit_ref 1.115 _refine_ls_restrained_S_all 1.114 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ag1 Ag 0.22809(5) 0.03046(5) 0.66352(13) 0.0181(3) Uani 1 1 d . . . S2 S 0.2115(2) -0.07771(19) 0.4117(3) 0.0163(5) Uani 1 1 d . . . S1 S 0.01062(19) 0.13580(17) 0.7043(2) 0.0162(5) Uani 1 1 d . . . C21 C 0.2556(13) -0.2397(8) 0.4160(17) 0.025(2) Uani 1 1 d . . . H21A H 0.2095 -0.2803 0.4948 0.037 Uiso 1 1 calc R . . H21B H 0.3456 -0.2471 0.4339 0.037 Uiso 1 1 calc R . . H21C H 0.2348 -0.2770 0.3214 0.037 Uiso 1 1 calc R . . C11 C 0.0593(10) 0.2932(8) 0.7421(14) 0.027(2) Uani 1 1 d . . . H11A H -0.0148 0.3424 0.7620 0.040 Uiso 1 1 calc R . . H11B H 0.1036 0.3254 0.6564 0.040 Uiso 1 1 calc R . . H11C H 0.1148 0.2947 0.8279 0.040 Uiso 1 1 calc R . . O1 O 0.3590(7) 0.1993(6) 0.6398(9) 0.0268(16) Uani 1 1 d . . . C1 C 0.3943(8) 0.2455(8) 0.7608(12) 0.021(2) Uani 1 1 d . . . C22 C 0.0407(8) -0.0833(7) 0.3886(12) 0.0165(18) Uani 1 1 d . . . H22A H 0.0061 -0.0020 0.4060 0.020 Uiso 1 1 calc R . . H22B H 0.0052 -0.1376 0.4642 0.020 Uiso 1 1 calc R . . F2 F 0.5382(8) 0.3903(7) 0.6535(12) 0.056(2) Uani 1 1 d . . . F3 F 0.3469(8) 0.4525(6) 0.6852(15) 0.060(3) Uani 1 1 d . . . O2 O 0.4006(9) 0.2014(6) 0.8859(10) 0.038(2) Uani 1 1 d . . . F1 F 0.4776(12) 0.4308(7) 0.8735(10) 0.064(3) Uani 1 1 d . . . C2 C 0.4390(10) 0.3831(9) 0.7454(12) 0.024(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ag1 0.0183(4) 0.0166(4) 0.0195(5) -0.0021(2) -0.0017(3) 0.00084(17) S2 0.0151(9) 0.0162(10) 0.0175(12) -0.0003(8) -0.0002(9) 0.0006(6) S1 0.0170(9) 0.0164(9) 0.0152(12) 0.0020(7) 0.0010(7) 0.0015(7) C21 0.025(4) 0.015(4) 0.035(6) -0.009(5) -0.005(4) 0.006(4) C11 0.032(5) 0.013(4) 0.035(7) 0.000(4) 0.004(5) 0.001(4) O1 0.031(3) 0.023(3) 0.026(4) -0.005(3) 0.009(3) -0.009(3) C1 0.018(4) 0.018(4) 0.028(6) -0.006(4) 0.004(4) 0.002(3) C22 0.010(3) 0.014(4) 0.025(6) 0.001(3) 0.003(4) 0.002(3) F2 0.053(4) 0.038(3) 0.076(6) 0.002(4) 0.028(5) -0.018(3) F3 0.042(4) 0.022(3) 0.115(9) 0.021(4) -0.025(6) -0.002(3) O2 0.064(5) 0.020(3) 0.030(5) 0.006(3) -0.013(4) -0.006(3) F1 0.122(9) 0.032(3) 0.038(5) -0.006(3) -0.013(5) -0.032(5) C2 0.023(5) 0.020(4) 0.030(6) 0.000(4) -0.004(4) 0.002(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Ag1 O1 . . 2.305(6) Y Ag1 S2 . . 2.539(3) Y Ag1 S1 . . 2.577(2) Y Ag1 S2 . 4 2.584(3) Y S2 C22 . . 1.803(9) Y S2 C21 . . 1.825(8) Y S2 Ag1 . 4_554 2.584(3) Y S1 C22 . 2 1.819(10) Y S1 C11 . . 1.82(1) Y C21 H21a . . 0.96 ? C21 H21b . . 0.96 ? C21 H21c . . 0.96 ? C11 H11a . . 0.96 ? C11 H11b . . 0.96 ? C11 H11c . . 0.96 ? O1 C1 . . 1.245(13) Y C1 O2 . . 1.216(12) Y C1 C2 . . 1.577(13) Y C22 S1 . 2_554 1.819(10) Y C22 H22a . . 0.97 ? C22 H22b . . 0.97 ? F2 C2 . . 1.326(13) Y F3 C2 . . 1.338(12) Y F1 C2 . . 1.317(12) Y loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 AG1 S2 . . . 109.3(2) Y O1 AG1 S1 . . . 100.57(18) Y S2 AG1 S1 . . . 105.72(7) Y O1 AG1 S2 . . 4 107.3(2) Y S2 AG1 S2 . . 4 124.10(8) Y S1 AG1 S2 . . 4 107.39(8) Y C22 S2 C21 . . . 102.7(5) Y C22 S2 AG1 . . . 100.6(3) Y C21 S2 AG1 . . . 114.4(5) Y C22 S2 AG1 . . 4_554 99.2(3) Y C21 S2 AG1 . . 4_554 113.4(5) Y AG1 S2 AG1 . . 4_554 121.82(8) Y C22 S1 C11 2 . . 102.3(5) Y C22 S1 AG1 2 . . 104.4(3) Y C11 S1 AG1 . . . 101.4(3) Y S2 C21 H21A . . . 109.5 ? S2 C21 H21B . . . 109.5 ? H21A C21 H21B . . . 109.5 ? S2 C21 H21C . . . 109.5 ? H21A C21 H21C . . . 109.5 ? H21B C21 H21C . . . 109.5 ? S1 C11 H11A . . . 109.5 ? S1 C11 H11B . . . 109.5 ? H11A C11 H11B . . . 109.5 ? S1 C11 H11C . . . 109.5 ? H11A C11 H11C . . . 109.5 ? H11B C11 H11C . . . 109.5 ? C1 O1 AG1 . . . 114.8(6) Y O2 C1 O1 . . . 130.5(9) Y O2 C1 C2 . . . 116.1(9) Y O1 C1 C2 . . . 113.4(9) Y S2 C22 S1 . . 2_554 114.0(5) Y S2 C22 H22A . . . 108.7 ? S1 C22 H22A 2_554 . . 108.7 ? S2 C22 H22B . . . 108.7 ? S1 C22 H22B 2_554 . . 108.7 ? H22A C22 H22B . . . 107.6 ? F1 C2 F2 . . . 105.7(10) Y F1 C2 F3 . . . 110.2(10) Y F2 C2 F3 . . . 106.5(10) Y F1 C2 C1 . . . 113.0(9) Y F2 C2 C1 . . . 110.1(8) Y F3 C2 C1 . . . 111.0(8) Y 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O1 AG1 S2 C22 . . . . -126.1(4) ? S1 AG1 S2 C22 . . . . -18.6(3) ? S2 AG1 S2 C22 4 . . . 105.8(3) ? O1 AG1 S2 C21 . . . . 124.5(5) ? S1 AG1 S2 C21 . . . . -128.0(5) ? S2 AG1 S2 C21 4 . . . -3.5(5) ? O1 AG1 S2 AG1 . . . 4_554 -18.1(2) ? S1 AG1 S2 AG1 . . . 4_554 89.39(10) ? S2 AG1 S2 AG1 4 . . 4_554 -146.17(12) ? O1 AG1 S1 C22 . . . 2 -119.2(4) ? S2 AG1 S1 C22 . . . 2 127.2(3) ? S2 AG1 S1 C22 4 . . 2 -7.1(3) ? O1 AG1 S1 C11 . . . . -13.2(4) ? S2 AG1 S1 C11 . . . . -126.9(4) ? S2 AG1 S1 C11 4 . . . 98.8(4) ? S2 AG1 O1 C1 . . . . -166.6(6) ? S1 AG1 O1 C1 . . . . 82.5(6) ? S2 AG1 O1 C1 4 . . . -29.6(7) ? AG1 O1 C1 O2 . . . . 21.9(13) ? AG1 O1 C1 C2 . . . . -158.9(6) ? C21 S2 C22 S1 . . . 2_554 -70.3(7) ? AG1 S2 C22 S1 . . . 2_554 171.4(4) ? AG1 S2 C22 S1 4_554 . . 2_554 46.4(4) ? O2 C1 C2 F1 . . . . 0.1(13) ? O1 C1 C2 F1 . . . . -179.2(9) ? O2 C1 C2 F2 . . . . 118.0(10) ? O1 C1 C2 F2 . . . . -61.3(11) ? O2 C1 C2 F3 . . . . -124.3(11) ? O1 C1 C2 F3 . . . . 56.4(12) ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 72.91 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 5.473 _refine_diff_density_min -1.690 _refine_diff_density_rms 0.376