data_lms129c06_0ma
_audit_creation_date               2023-01-31
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number       '2014/7'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C16 H16 F N O2 S'
_chemical_formula_sum              'C16 H16 F N O2 S'
_chemical_formula_weight           305.36
_chemical_absolute_configuration   ?
_chemical_melting_point            ?
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'
 'F' 'F' 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0311 0.0180 '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'
 'S' 'S' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             9
_space_group_name_H-M_alt          'C 1 c 1'
_space_group_name_Hall             'C -2yc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 'x, -y, z+1/2'
 'x+1/2, y+1/2, z'
 'x+1/2, -y+1/2, z+1/2'

_cell_length_a                     17.2716(14)
_cell_length_b                     11.7864(14)
_cell_length_c                     7.4972(7)
_cell_angle_alpha                  90
_cell_angle_beta                   92.385(6)
_cell_angle_gamma                  90
_cell_volume                       1524.9(3)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      7444
_cell_measurement_temperature      298.0
_cell_measurement_theta_max        71.904
_cell_measurement_theta_min        4.542
_shelx_estimated_absorpt_T_max     0.980
_shelx_estimated_absorpt_T_min     0.961
_exptl_absorpt_coefficient_mu      2.019
_exptl_absorpt_correction_T_max    0.7535
_exptl_absorpt_correction_T_min    0.5453
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1304 before and 0.0657 after correction.
The Ratio of minimum to maximum transmission is 0.7237.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.330
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               640
_exptl_crystal_preparation         ?
_exptl_crystal_size_max            0.02
_exptl_crystal_size_mid            0.01
_exptl_crystal_size_min            0.01
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0543
_diffrn_reflns_av_unetI/netI       0.0408
_diffrn_reflns_Laue_measured_fraction_full  0.997
_diffrn_reflns_Laue_measured_fraction_max  0.996
_diffrn_reflns_limit_h_max         21
_diffrn_reflns_limit_h_min         -21
_diffrn_reflns_limit_k_max         14
_diffrn_reflns_limit_k_min         -14
_diffrn_reflns_limit_l_max         8
_diffrn_reflns_limit_l_min         -9
_diffrn_reflns_number              12375
_diffrn_reflns_point_group_measured_fraction_full  0.942
_diffrn_reflns_point_group_measured_fraction_max  0.931
_diffrn_reflns_theta_full          67.679
_diffrn_reflns_theta_max           72.124
_diffrn_reflns_theta_min           4.543
_diffrn_ambient_temperature        298.0
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.997
_diffrn_measured_fraction_theta_max  0.996
_diffrn_measurement_device_type    'Bruker CMOS area detector'
_diffrn_measurement_method         ?
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54178
_diffrn_source                     ?
_diffrn_source_current             1.1
_diffrn_source_power               0.055
_diffrn_source_voltage             50.0
_diffrn_special_details            ?
_reflns_Friedel_coverage           0.866
_reflns_Friedel_fraction_full      0.887
_reflns_Friedel_fraction_max       0.866
_reflns_number_gt                  2625
_reflns_number_total               2802
_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.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         ws0805
_computing_data_collection         ?
_computing_data_reduction          ws0805
_computing_molecular_graphics      'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max           0.195
_refine_diff_density_min           -0.131
_refine_diff_density_rms           0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 1102 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     0.116(9)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.055
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       192
_refine_ls_number_reflns           2802
_refine_ls_number_restraints       2
_refine_ls_R_factor_all            0.0375
_refine_ls_R_factor_gt             0.0349
_refine_ls_restrained_S_all        1.054
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0509P)²+0.1650P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0890
_refine_ls_wR_factor_ref           0.0913
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C6(H6), C13(H13), C4(H4), C7(H7), C3(H3), C16(H16), C15(H15)
2.b X=CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
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 0.52537(6) 0.73366(7) 0.32946(10) 0.0709(3) Uani 1 1 d . . . . .
 O1 O 0.47860(16) 0.6398(3) 0.2741(3) 0.0873(8) Uani 1 1 d . . . . .
 F1 F 0.15535(14) 0.5562(3) 0.4137(4) 0.1075(8) Uani 1 1 d . . . . .
 C5 C 0.61756(19) 0.6819(2) 0.3996(4) 0.0606(7) Uani 1 1 d . . . . .
 O2 O 0.53693(18) 0.8262(3) 0.2095(4) 0.1025(10) Uani 1 1 d . . . . .
 C12 C 0.32444(18) 0.7341(2) 0.4644(4) 0.0605(7) Uani 1 1 d . . . . .
 H12 H 0.3410 0.8052 0.4282 0.073 Uiso 1 1 calc R U . . .
 C2 C 0.7636(2) 0.6017(3) 0.5117(4) 0.0703(8) Uani 1 1 d . . . . .
 C11 C 0.37446(17) 0.6665(2) 0.5681(4) 0.0563(6) Uani 1 1 d . . . . .
 C6 C 0.6252(2) 0.5767(3) 0.4838(5) 0.0738(9) Uani 1 1 d . . . . .
 H6 H 0.5816 0.5326 0.5023 0.089 Uiso 1 1 calc R U . . .
 C13 C 0.25022(19) 0.6981(3) 0.4135(5) 0.0663(7) Uani 1 1 d . . . . .
 H13 H 0.2169 0.7443 0.3453 0.080 Uiso 1 1 calc R U . . .
 C4 C 0.6829(2) 0.7466(3) 0.3718(5) 0.0694(8) Uani 1 1 d . . . . .
 H4 H 0.6783 0.8169 0.3161 0.083 Uiso 1 1 calc R U . . .
 C7 C 0.6978(2) 0.5384(3) 0.5395(5) 0.0778(9) Uani 1 1 d . . . . .
 H7 H 0.7026 0.4687 0.5968 0.093 Uiso 1 1 calc R U . . .
 C14 C 0.2275(2) 0.5927(3) 0.4665(4) 0.0695(8) Uani 1 1 d . . . . .
 C3 C 0.7553(2) 0.7057(3) 0.4278(5) 0.0735(8) Uani 1 1 d . . . . .
 H3 H 0.7991 0.7492 0.4085 0.088 Uiso 1 1 calc R U . . .
 N1 N 0.48682(17) 0.7875(2) 0.5079(4) 0.0735(7) Uani 1 1 d . . . . .
 C16 C 0.3486(2) 0.5592(2) 0.6164(4) 0.0676(8) Uani 1 1 d . . . . .
 H16 H 0.3813 0.5114 0.6833 0.081 Uiso 1 1 calc R U . . .
 C15 C 0.2747(2) 0.5233(3) 0.5658(5) 0.0740(8) Uani 1 1 d . . . . .
 H15 H 0.2575 0.4520 0.5997 0.089 Uiso 1 1 calc R U . . .
 C9 C 0.45119(19) 0.7097(3) 0.6288(4) 0.0687(8) Uani 1 1 d . . . . .
 C1 C 0.8432(3) 0.5594(4) 0.5698(6) 0.0958(12) Uani 1 1 d . . . . .
 H1A H 0.8386 0.5019 0.6595 0.144 Uiso 1 1 calc R U . . .
 H1B H 0.8736 0.6213 0.6178 0.144 Uiso 1 1 calc R U . . .
 H1C H 0.8681 0.5279 0.4689 0.144 Uiso 1 1 calc R U . . .
 C8 C 0.5282(2) 0.8872(4) 0.5829(8) 0.1073(16) Uani 1 1 d . . . . .
 H8A H 0.5804 0.8664 0.6174 0.161 Uiso 1 1 calc R U . . .
 H8B H 0.5023 0.9141 0.6856 0.161 Uiso 1 1 calc R U . . .
 H8C H 0.5289 0.9462 0.4946 0.161 Uiso 1 1 calc R U . . .
 C10 C 0.4827(3) 0.6880(5) 0.7895(6) 0.1074(15) Uani 1 1 d . . . . .
 H10A H 0.5288 0.7232 0.8266 0.129 Uiso 1 1 calc R U . . .
 H10B H 0.4587 0.6376 0.8650 0.129 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 O1 1.422(3) . ?
 S1 C5 1.765(3) . ?
 S1 O2 1.433(3) . ?
 S1 N1 1.646(3) . ?
 F1 C14 1.362(4) . ?
 C5 C6 1.395(5) . ?
 C5 C4 1.385(4) . ?
 C12 H12 0.9300 . ?
 C12 C11 1.390(4) . ?
 C12 C13 1.389(4) . ?
 C2 C7 1.381(5) . ?
 C2 C3 1.382(5) . ?
 C2 C1 1.511(6) . ?
 C11 C16 1.394(4) . ?
 C11 C9 1.474(4) . ?
 C6 H6 0.9300 . ?
 C6 C7 1.382(6) . ?
 C13 H13 0.9300 . ?
 C13 C14 1.366(5) . ?
 C4 H4 0.9300 . ?
 C4 C3 1.390(6) . ?
 C7 H7 0.9300 . ?
 C14 C15 1.356(5) . ?
 C3 H3 0.9300 . ?
 N1 C9 1.444(5) . ?
 N1 C8 1.476(4) . ?
 C16 H16 0.9300 . ?
 C16 C15 1.382(5) . ?
 C15 H15 0.9300 . ?
 C9 C10 1.327(6) . ?
 C1 H1A 0.9600 . ?
 C1 H1B 0.9600 . ?
 C1 H1C 0.9600 . ?
 C8 H8A 0.9600 . ?
 C8 H8B 0.9600 . ?
 C8 H8C 0.9600 . ?
 C10 H10A 0.9300 . ?
 C10 H10B 0.9300 . ?

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 S1 C5 108.21(18) . . ?
 O1 S1 O2 120.09(19) . . ?
 O1 S1 N1 107.05(14) . . ?
 O2 S1 C5 107.61(17) . . ?
 O2 S1 N1 106.8(2) . . ?
 N1 S1 C5 106.36(15) . . ?
 C6 C5 S1 120.6(2) . . ?
 C4 C5 S1 119.7(3) . . ?
 C4 C5 C6 119.7(3) . . ?
 C11 C12 H12 119.2 . . ?
 C13 C12 H12 119.2 . . ?
 C13 C12 C11 121.5(3) . . ?
 C7 C2 C3 118.6(3) . . ?
 C7 C2 C1 121.5(4) . . ?
 C3 C2 C1 120.0(4) . . ?
 C12 C11 C16 117.9(3) . . ?
 C12 C11 C9 120.3(3) . . ?
 C16 C11 C9 121.8(3) . . ?
 C5 C6 H6 120.2 . . ?
 C7 C6 C5 119.6(3) . . ?
 C7 C6 H6 120.2 . . ?
 C12 C13 H13 120.9 . . ?
 C14 C13 C12 118.1(3) . . ?
 C14 C13 H13 120.9 . . ?
 C5 C4 H4 120.2 . . ?
 C5 C4 C3 119.5(3) . . ?
 C3 C4 H4 120.2 . . ?
 C2 C7 C6 121.3(3) . . ?
 C2 C7 H7 119.3 . . ?
 C6 C7 H7 119.3 . . ?
 F1 C14 C13 118.2(3) . . ?
 C15 C14 F1 119.4(3) . . ?
 C15 C14 C13 122.4(3) . . ?
 C2 C3 C4 121.3(3) . . ?
 C2 C3 H3 119.4 . . ?
 C4 C3 H3 119.4 . . ?
 C9 N1 S1 117.5(2) . . ?
 C9 N1 C8 118.6(4) . . ?
 C8 N1 S1 114.3(3) . . ?
 C11 C16 H16 119.7 . . ?
 C15 C16 C11 120.6(3) . . ?
 C15 C16 H16 119.7 . . ?
 C14 C15 C16 119.5(3) . . ?
 C14 C15 H15 120.3 . . ?
 C16 C15 H15 120.3 . . ?
 N1 C9 C11 115.3(3) . . ?
 C10 C9 C11 122.9(4) . . ?
 C10 C9 N1 121.5(4) . . ?
 C2 C1 H1A 109.5 . . ?
 C2 C1 H1B 109.5 . . ?
 C2 C1 H1C 109.5 . . ?
 H1A C1 H1B 109.5 . . ?
 H1A C1 H1C 109.5 . . ?
 H1B C1 H1C 109.5 . . ?
 N1 C8 H8A 109.5 . . ?
 N1 C8 H8B 109.5 . . ?
 N1 C8 H8C 109.5 . . ?
 H8A C8 H8B 109.5 . . ?
 H8A C8 H8C 109.5 . . ?
 H8B C8 H8C 109.5 . . ?
 C9 C10 H10A 120.0 . . ?
 C9 C10 H10B 120.0 . . ?
 H10A C10 H10B 120.0 . . ?

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
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 S1 C5 C6 C7 -179.2(3) . . . . ?
 S1 C5 C4 C3 179.8(3) . . . . ?
 S1 N1 C9 C11 -76.1(3) . . . . ?
 S1 N1 C9 C10 109.9(4) . . . . ?
 O1 S1 C5 C6 -34.1(3) . . . . ?
 O1 S1 C5 C4 146.3(3) . . . . ?
 O1 S1 N1 C9 34.6(3) . . . . ?
 O1 S1 N1 C8 -179.6(3) . . . . ?
 F1 C14 C15 C16 178.6(3) . . . . ?
 C5 S1 N1 C9 -80.9(2) . . . . ?
 C5 S1 N1 C8 64.9(3) . . . . ?
 C5 C6 C7 C2 -0.8(5) . . . . ?
 C5 C4 C3 C2 -0.3(5) . . . . ?
 O2 S1 C5 C6 -165.3(3) . . . . ?
 O2 S1 C5 C4 15.1(3) . . . . ?
 O2 S1 N1 C9 164.4(2) . . . . ?
 O2 S1 N1 C8 -49.8(3) . . . . ?
 C12 C11 C16 C15 -1.6(5) . . . . ?
 C12 C11 C9 N1 -32.4(4) . . . . ?
 C12 C11 C9 C10 141.5(4) . . . . ?
 C12 C13 C14 F1 -178.6(3) . . . . ?
 C12 C13 C14 C15 -0.1(5) . . . . ?
 C11 C12 C13 C14 -0.8(5) . . . . ?
 C11 C16 C15 C14 0.8(5) . . . . ?
 C6 C5 C4 C3 0.2(5) . . . . ?
 C13 C12 C11 C16 1.6(5) . . . . ?
 C13 C12 C11 C9 -176.4(3) . . . . ?
 C13 C14 C15 C16 0.1(5) . . . . ?
 C4 C5 C6 C7 0.4(5) . . . . ?
 C7 C2 C3 C4 -0.1(5) . . . . ?
 C3 C2 C7 C6 0.6(5) . . . . ?
 N1 S1 C5 C6 80.6(3) . . . . ?
 N1 S1 C5 C4 -99.0(3) . . . . ?
 C16 C11 C9 N1 149.7(3) . . . . ?
 C16 C11 C9 C10 -36.5(5) . . . . ?
 C9 C11 C16 C15 176.4(3) . . . . ?
 C1 C2 C7 C6 -179.0(3) . . . . ?
 C1 C2 C3 C4 179.6(3) . . . . ?
 C8 N1 C9 C11 139.5(3) . . . . ?
 C8 N1 C9 C10 -34.4(5) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
