 
data_20170930lmf_0m_a
 
_audit_creation_method            'SHELXL-2016/6'
_shelx_SHELXL_version_number      '2016/6'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C12 H10 F3 N O2 S' 
_chemical_formula_weight          289.27

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'
 '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'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/n'
_space_group_name_Hall            '-P 2yn'
 
_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+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                    12.5508(18)
_cell_length_b                    4.7813(7)
_cell_length_c                    20.425(3)
_cell_angle_alpha                 90
_cell_angle_beta                  103.082(4)
_cell_angle_gamma                 90
_cell_volume                      1193.9(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     153(2)
_cell_measurement_reflns_used      3559
_cell_measurement_theta_min        3.15
_cell_measurement_theta_max       27.43
 
_exptl_crystal_description        ''
_exptl_crystal_colour             ''
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.609          
_exptl_crystal_F_000              592
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.250
_exptl_crystal_size_mid           0.220
_exptl_crystal_size_min           0.190
_exptl_absorpt_coefficient_mu     0.307
_shelx_estimated_absorpt_T_min    0.927
_shelx_estimated_absorpt_T_max    0.944
_exptl_absorpt_correction_type    ?
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       153(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             7354
_diffrn_reflns_av_unetI/netI      0.0337
_diffrn_reflns_av_R_equivalents   0.0345
_diffrn_reflns_limit_h_min        -14
_diffrn_reflns_limit_h_max        14
_diffrn_reflns_limit_k_min        -5
_diffrn_reflns_limit_k_max        5
_diffrn_reflns_limit_l_min        -19
_diffrn_reflns_limit_l_max        24
_diffrn_reflns_theta_min          2.144
_diffrn_reflns_theta_max          25.007
_diffrn_reflns_theta_full         25.007
_diffrn_measured_fraction_theta_max   0.997
_diffrn_measured_fraction_theta_full  0.997
_diffrn_reflns_Laue_measured_fraction_max    0.997
_diffrn_reflns_Laue_measured_fraction_full   0.997
_diffrn_reflns_point_group_measured_fraction_max   0.997
_diffrn_reflns_point_group_measured_fraction_full  0.997
_reflns_number_total              2097
_reflns_number_gt                 1725
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution     'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0413P)²+0.8245P] 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_number_reflns          2097
_refine_ls_number_parameters      173
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0462
_refine_ls_R_factor_gt            0.0346
_refine_ls_wR_factor_ref          0.0879
_refine_ls_wR_factor_gt           0.0824
_refine_ls_goodness_of_fit_ref    1.007
_refine_ls_restrained_S_all       1.007
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_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
C1 C 0.31618(17) 0.0547(5) 0.64594(12) 0.0297(5) Uani 1 1 d . . . . .
H1A H 0.268759 0.081929 0.601188 0.044 Uiso 1 1 calc R U . . .
H1B H 0.273165 0.077354 0.680100 0.044 Uiso 1 1 calc R U . . .
H1C H 0.347596 -0.133753 0.649074 0.044 Uiso 1 1 calc R U . . .
C2 C 0.46973(16) 0.2514(4) 0.61364(10) 0.0189(4) Uani 1 1 d . . . . .
C3 C 0.55780(16) 0.4588(4) 0.62981(10) 0.0184(4) Uani 1 1 d . . . . .
C4 C 0.57384(16) 0.6304(4) 0.68608(10) 0.0198(4) Uani 1 1 d . . . . .
H4 H 0.526002 0.613795 0.715874 0.024 Uiso 1 1 calc R U . . .
C5 C 0.65842(16) 0.8269(4) 0.70006(10) 0.0214(5) Uani 1 1 d . . . . .
H5 H 0.666180 0.942954 0.738606 0.026 Uiso 1 1 calc R U . . .
C6 C 0.73118(16) 0.8550(4) 0.65850(10) 0.0193(4) Uani 1 1 d . . . . .
H6 H 0.788511 0.988899 0.668240 0.023 Uiso 1 1 calc R U . . .
C7 C 0.71857(15) 0.6824(4) 0.60199(10) 0.0182(4) Uani 1 1 d . . . . .
C8 C 0.63172(16) 0.4887(4) 0.58785(9) 0.0177(4) Uani 1 1 d . . . . .
C9 C 0.72476(16) 0.4498(5) 0.50719(10) 0.0208(5) Uani 1 1 d . . . . .
H9 H 0.745640 0.388102 0.467683 0.025 Uiso 1 1 calc R U . . .
C10 C 0.77747(16) 0.6515(4) 0.54965(10) 0.0198(4) Uani 1 1 d . . . . .
C11 C 1.00745(16) 0.6408(5) 0.58137(10) 0.0240(5) Uani 1 1 d . . . . .
H11A H 0.989207 0.440179 0.573875 0.029 Uiso 1 1 calc R U . . .
H11B H 1.069715 0.681482 0.560541 0.029 Uiso 1 1 calc R U . . .
C12 C 1.04308(17) 0.6912(5) 0.65537(11) 0.0254(5) Uani 1 1 d . . . . .
F1 F 0.97234(11) 0.5938(3) 0.68947(6) 0.0401(4) Uani 1 1 d . . . . .
F2 F 1.05863(12) 0.9618(3) 0.67086(7) 0.0425(4) Uani 1 1 d . . . . .
F3 F 1.13941(10) 0.5637(3) 0.68049(7) 0.0401(4) Uani 1 1 d . . . . .
N1 N 0.63770(13) 0.3496(4) 0.52965(8) 0.0195(4) Uani 1 1 d . . . . .
H1 H 0.592674 0.217573 0.510171 0.023 Uiso 1 1 calc R U . . .
O1 O 0.40307(11) 0.2589(3) 0.65693(7) 0.0256(4) Uani 1 1 d . . . . .
O2 O 0.45635(11) 0.0901(3) 0.56637(7) 0.0234(3) Uani 1 1 d . . . . .
S1 S 0.89070(4) 0.84668(11) 0.53885(3) 0.02293(16) Uani 1 1 d . . . . .
 
 
_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
C1 O1 1.443(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O2 1.218(2) . ?
C2 O1 1.348(2) . ?
C2 C3 1.466(3) . ?
C3 C4 1.389(3) . ?
C3 C8 1.406(3) . ?
C4 C5 1.398(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.398(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.410(3) . ?
C7 C10 1.438(3) . ?
C8 N1 1.379(3) . ?
C9 C10 1.364(3) . ?
C9 N1 1.364(3) . ?
C9 H9 0.9500 . ?
C10 S1 1.755(2) . ?
C11 C12 1.496(3) . ?
C11 S1 1.815(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 F1 1.330(2) . ?
C12 F2 1.336(3) . ?
C12 F3 1.348(2) . ?
N1 H1 0.8800 . ?
 
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
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 122.83(19) . . ?
O2 C2 C3 124.68(18) . . ?
O1 C2 C3 112.49(17) . . ?
C4 C3 C8 116.89(19) . . ?
C4 C3 C2 123.13(18) . . ?
C8 C3 C2 119.98(18) . . ?
C3 C4 C5 121.81(19) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 120.99(19) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 118.75(19) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C6 C7 C8 119.64(18) . . ?
C6 C7 C10 133.87(19) . . ?
C8 C7 C10 106.49(17) . . ?
N1 C8 C3 130.45(19) . . ?
N1 C8 C7 107.64(17) . . ?
C3 C8 C7 121.91(18) . . ?
C10 C9 N1 110.16(18) . . ?
C10 C9 H9 124.9 . . ?
N1 C9 H9 124.9 . . ?
C9 C10 C7 106.77(18) . . ?
C9 C10 S1 125.88(16) . . ?
C7 C10 S1 127.26(16) . . ?
C12 C11 S1 114.87(15) . . ?
C12 C11 H11A 108.5 . . ?
S1 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
S1 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
F1 C12 F2 107.10(18) . . ?
F1 C12 F3 106.85(17) . . ?
F2 C12 F3 106.12(17) . . ?
F1 C12 C11 112.98(18) . . ?
F2 C12 C11 112.92(18) . . ?
F3 C12 C11 110.44(18) . . ?
C9 N1 C8 108.94(17) . . ?
C9 N1 H1 125.5 . . ?
C8 N1 H1 125.5 . . ?
C2 O1 C1 116.06(16) . . ?
C10 S1 C11 103.91(10) . . ?
 
_refine_diff_density_max    0.256
_refine_diff_density_min   -0.185
_refine_diff_density_rms    0.050



