 
data_Gandelman335b
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             'Gandelman335b (Andreii)'
_chemical_melting_point           ?
_chemical_formula_moiety          'C24 H21 F3 S'
_chemical_formula_sum
 'C24 H21 F3 S' 
_chemical_formula_weight          398.47

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'
 'F'  'F'   0.0171   0.0103
 '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'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            4
_space_group_name_H-M_alt         'P 21'
_space_group_name_Hall            'P 2yb'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z'
 
_cell_length_a                    10.2316(9)
_cell_length_b                    6.1453(5)
_cell_length_c                    16.0261(14)
_cell_angle_alpha                 90
_cell_angle_beta                  92.615(2)
_cell_angle_gamma                 90
_cell_volume                      1006.61(15)
_cell_formula_units_Z             2
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     3484
_cell_measurement_theta_min       1.272
_cell_measurement_theta_max       25.065
 
_exptl_crystal_description        needle
_exptl_crystal_colour             colorless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.315          
_exptl_crystal_F_000              416
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.240
_exptl_crystal_size_mid           0.120
_exptl_crystal_size_min           0.120
_exptl_absorpt_coefficient_mu     0.194
_shelx_estimated_absorpt_T_min    0.955
_shelx_estimated_absorpt_T_max    0.977
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_correction_T_min   0.800
_exptl_absorpt_correction_T_max   0.859
_exptl_absorpt_process_details    'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'APEX2 (Bruker AXS)'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  95
_diffrn_reflns_number             7841
_diffrn_reflns_av_unetI/netI      0.0525
_diffrn_reflns_av_R_equivalents   0.0568
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -7
_diffrn_reflns_limit_k_max        7
_diffrn_reflns_limit_l_min        -19
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          1.272
_diffrn_reflns_theta_max          25.065
_diffrn_reflns_theta_full         25.065
_diffrn_measured_fraction_theta_max   0.996
_diffrn_measured_fraction_theta_full  0.996
_diffrn_reflns_Laue_measured_fraction_max    0.996
_diffrn_reflns_Laue_measured_fraction_full   0.996
_diffrn_reflns_point_group_measured_fraction_max   0.977
_diffrn_reflns_point_group_measured_fraction_full  0.977
_reflns_number_total              3484
_reflns_number_gt                 3208
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.778
_reflns_Friedel_fraction_max      0.953
_reflns_Friedel_fraction_full     0.954
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker Instrument Service v2010.7.0.0'
_computing_cell_refinement        'APEX2 v2010.7-0 (Bruker AXS)'
_computing_data_reduction         'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution     'SIR2004 (Burla et al., 2007)'
_computing_structure_refinement   'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material   'Olex2 (Dolomanov et al., 2009)'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0445P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_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 x determined using 1321 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    0.00(7)
_chemical_absolute_configuration  unk
_refine_ls_number_reflns          3484
_refine_ls_number_parameters      255
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0375
_refine_ls_R_factor_gt            0.0341
_refine_ls_wR_factor_ref          0.0806
_refine_ls_wR_factor_gt           0.0793
_refine_ls_goodness_of_fit_ref    1.003
_refine_ls_restrained_S_all       1.003
_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_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
S1 S -0.73781(7) -0.43790(11) -0.17768(4) 0.02145(19) Uani 1 1 d . . . . .
F1 F -0.57546(17) -0.2584(3) -0.02650(11) 0.0365(5) Uani 1 1 d . . . . .
F2 F -0.55872(19) -0.0316(3) -0.12793(12) 0.0382(5) Uani 1 1 d . . . . .
F3 F -0.39318(17) -0.2255(3) -0.08637(12) 0.0349(5) Uani 1 1 d . . . . .
C1 C -0.9130(3) -0.6891(4) -0.10092(17) 0.0194(6) Uani 1 1 d . . . . .
C2 C -0.9362(3) -0.8872(4) -0.13962(19) 0.0287(8) Uani 1 1 d . . . . .
H2 H -0.8651 -0.9694 -0.1591 0.034 Uiso 1 1 calc R U . . .
C3 C -1.0631(4) -0.9670(5) -0.1502(2) 0.0383(9) Uani 1 1 d . . . . .
H3 H -1.0786 -1.1038 -0.1765 0.046 Uiso 1 1 calc R U . . .
C4 C -1.1661(3) -0.8477(5) -0.1226(2) 0.0362(9) Uani 1 1 d . . . . .
H4 H -1.2528 -0.9022 -0.1297 0.043 Uiso 1 1 calc R U . . .
C5 C -1.1439(3) -0.6487(6) -0.0845(2) 0.0293(8) Uani 1 1 d . . . . .
H5 H -1.2153 -0.5661 -0.0657 0.035 Uiso 1 1 calc R U . . .
C6 C -1.0180(3) -0.5697(4) -0.07369(18) 0.0214(7) Uani 1 1 d . . . . .
H6 H -1.0032 -0.4327 -0.0475 0.026 Uiso 1 1 calc R U . . .
C7 C -0.7761(3) -0.6037(5) -0.08770(19) 0.0266(7) Uani 1 1 d . . . . .
H7A H -0.7136 -0.7262 -0.0816 0.032 Uiso 1 1 calc R U . . .
H7B H -0.7690 -0.5148 -0.0361 0.032 Uiso 1 1 calc R U . . .
C8 C -0.5613(3) -0.4093(5) -0.16279(18) 0.0212(6) Uani 1 1 d . . . . .
H8 H -0.5262 -0.5493 -0.1392 0.025 Uiso 1 1 calc R U . . .
C9 C -0.5239(3) -0.2302(5) -0.1014(2) 0.0259(7) Uani 1 1 d . . . . .
C10 C -0.4993(3) -0.3723(4) -0.24604(18) 0.0192(6) Uani 1 1 d . . . . .
C11 C -0.5545(3) -0.2267(4) -0.30407(19) 0.0221(7) Uani 1 1 d . . . . .
H11 H -0.6304 -0.1471 -0.2908 0.026 Uiso 1 1 calc R U . . .
C12 C -0.5002(3) -0.1959(4) -0.3812(2) 0.0229(7) Uani 1 1 d . . . . .
H12 H -0.5391 -0.0981 -0.4210 0.027 Uiso 1 1 calc R U . . .
C13 C -0.3878(3) -0.3116(4) -0.39881(18) 0.0188(6) Uani 1 1 d . . . . .
C14 C -0.3122(3) -0.3188(4) -0.47491(19) 0.0203(6) Uani 1 1 d . . . . .
C15 C -0.3308(3) -0.2130(5) -0.55065(19) 0.0246(7) Uani 1 1 d . . . . .
H15 H -0.3986 -0.1087 -0.5590 0.030 Uiso 1 1 calc R U . . .
C16 C -0.2476(3) -0.2628(5) -0.6145(2) 0.0286(7) Uani 1 1 d . . . . .
H16 H -0.2582 -0.1910 -0.6668 0.034 Uiso 1 1 calc R U . . .
C17 C -0.1497(3) -0.4163(5) -0.60197(19) 0.0282(7) Uani 1 1 d . . . . .
H17 H -0.0954 -0.4513 -0.6466 0.034 Uiso 1 1 calc R U . . .
C18 C -0.1293(3) -0.5202(5) -0.52555(19) 0.0238(7) Uani 1 1 d . . . . .
H18 H -0.0607 -0.6233 -0.5173 0.029 Uiso 1 1 calc R U . . .
C19 C -0.2105(3) -0.4710(4) -0.46174(17) 0.0193(6) Uani 1 1 d . . . . .
C20 C -0.2095(3) -0.5615(4) -0.37352(18) 0.0183(6) Uani 1 1 d . . . . .
C21 C -0.3307(2) -0.4550(4) -0.34039(17) 0.0169(6) Uani 1 1 d . . . . .
C22 C -0.3867(3) -0.4868(4) -0.26429(18) 0.0185(6) Uani 1 1 d . . . . .
H22 H -0.3486 -0.5860 -0.2248 0.022 Uiso 1 1 calc R U . . .
C23 C -0.0866(3) -0.4894(4) -0.32346(18) 0.0218(7) Uani 1 1 d . . . . .
H23A H -0.0818 -0.3301 -0.3230 0.033 Uiso 1 1 calc R U . . .
H23B H -0.0091 -0.5487 -0.3492 0.033 Uiso 1 1 calc R U . . .
H23C H -0.0898 -0.5430 -0.2660 0.033 Uiso 1 1 calc R U . . .
C24 C -0.2219(3) -0.8115(4) -0.3743(2) 0.0231(7) Uani 1 1 d . . . . .
H24A H -0.2249 -0.8651 -0.3169 0.035 Uiso 1 1 calc R U . . .
H24B H -0.1464 -0.8748 -0.4009 0.035 Uiso 1 1 calc R U . . .
H24C H -0.3024 -0.8534 -0.4058 0.035 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
S1 C8 1.819(3) . ?
S1 C7 1.823(3) . ?
F1 C9 1.343(3) . ?
F2 C9 1.336(4) . ?
F3 C9 1.349(3) . ?
C1 C2 1.382(4) . ?
C1 C6 1.388(4) . ?
C1 C7 1.502(4) . ?
C2 C3 1.391(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.373(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.514(4) . ?
C8 C10 1.520(4) . ?
C8 H8 1.0000 . ?
C10 C11 1.392(4) . ?
C10 C22 1.392(4) . ?
C11 C12 1.390(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.392(4) . ?
C12 H12 0.9500 . ?
C13 C21 1.395(4) . ?
C13 C14 1.474(4) . ?
C14 C15 1.382(4) . ?
C14 C19 1.408(4) . ?
C15 C16 1.394(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.389(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.380(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.519(4) . ?
C20 C21 1.519(4) . ?
C20 C23 1.527(4) . ?
C20 C24 1.541(4) . ?
C21 C22 1.385(4) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C8 S1 C7 101.42(13) . . ?
C2 C1 C6 119.2(3) . . ?
C2 C1 C7 120.8(3) . . ?
C6 C1 C7 120.1(3) . . ?
C1 C2 C3 120.4(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 120.4(3) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C1 C7 S1 108.4(2) . . ?
C1 C7 H7A 110.0 . . ?
S1 C7 H7A 110.0 . . ?
C1 C7 H7B 110.0 . . ?
S1 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
C9 C8 C10 111.0(2) . . ?
C9 C8 S1 112.05(19) . . ?
C10 C8 S1 110.5(2) . . ?
C9 C8 H8 107.7 . . ?
C10 C8 H8 107.7 . . ?
S1 C8 H8 107.7 . . ?
F2 C9 F1 107.0(2) . . ?
F2 C9 F3 106.6(2) . . ?
F1 C9 F3 105.7(3) . . ?
F2 C9 C8 113.6(3) . . ?
F1 C9 C8 112.9(2) . . ?
F3 C9 C8 110.5(2) . . ?
C11 C10 C22 119.9(3) . . ?
C11 C10 C8 120.6(2) . . ?
C22 C10 C8 119.4(3) . . ?
C12 C11 C10 121.0(3) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 118.6(3) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C12 C13 C21 120.8(3) . . ?
C12 C13 C14 130.8(3) . . ?
C21 C13 C14 108.5(2) . . ?
C15 C14 C19 121.0(3) . . ?
C15 C14 C13 131.0(3) . . ?
C19 C14 C13 107.9(2) . . ?
C14 C15 C16 118.5(3) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C17 C16 C15 120.4(3) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 121.3(3) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C19 C18 C17 118.8(3) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
C18 C19 C14 120.0(3) . . ?
C18 C19 C20 129.1(3) . . ?
C14 C19 C20 110.9(2) . . ?
C21 C20 C19 101.4(2) . . ?
C21 C20 C23 110.9(2) . . ?
C19 C20 C23 110.7(2) . . ?
C21 C20 C24 111.4(2) . . ?
C19 C20 C24 111.1(2) . . ?
C23 C20 C24 111.1(2) . . ?
C22 C21 C13 120.2(2) . . ?
C22 C21 C20 128.6(3) . . ?
C13 C21 C20 111.2(2) . . ?
C21 C22 C10 119.6(3) . . ?
C21 C22 H22 120.2 . . ?
C10 C22 H22 120.2 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
 
_refine_diff_density_max    0.208
_refine_diff_density_min   -0.234
_refine_diff_density_rms    0.038



