data_bjm04_0m
_audit_creation_date               2021-01-07
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number       '2018/3'
_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           'C12 H15 N O3 S'
_chemical_formula_sum              'C12 H15 N O3 S'
_chemical_formula_weight           253.31
_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' 0.0033 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'
 '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'

_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             4
_space_group_name_H-M_alt          'P 1 21 1'
_space_group_name_Hall             'P 2yb'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z'

_cell_length_a                     5.5075(16)
_cell_length_b                     5.6395(15)
_cell_length_c                     19.524(6)
_cell_angle_alpha                  90
_cell_angle_beta                   93.936(9)
_cell_angle_gamma                  90
_cell_volume                       605.0(3)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      1897
_cell_measurement_temperature      150.0
_cell_measurement_theta_max        21.838
_cell_measurement_theta_min        3.138
_shelx_estimated_absorpt_T_max     0.969
_shelx_estimated_absorpt_T_min     0.913
_exptl_absorpt_coefficient_mu      0.263
_exptl_absorpt_correction_T_max    0.7456
_exptl_absorpt_correction_T_min    0.5398
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1259 before and 0.0932 after correction.
The Ratio of minimum to maximum transmission is 0.7240.
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      1.391
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         plate
_exptl_crystal_F_000               268
_exptl_crystal_size_max            0.35
_exptl_crystal_size_mid            0.3
_exptl_crystal_size_min            0.12
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0876
_diffrn_reflns_av_unetI/netI       0.0987
_diffrn_reflns_Laue_measured_fraction_full  0.999
_diffrn_reflns_Laue_measured_fraction_max  0.999
_diffrn_reflns_limit_h_max         6
_diffrn_reflns_limit_h_min         -7
_diffrn_reflns_limit_k_max         7
_diffrn_reflns_limit_k_min         -7
_diffrn_reflns_limit_l_max         25
_diffrn_reflns_limit_l_min         -25
_diffrn_reflns_number              9492
_diffrn_reflns_point_group_measured_fraction_full  1.000
_diffrn_reflns_point_group_measured_fraction_max  1.000
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           27.458
_diffrn_reflns_theta_min           2.091
_diffrn_ambient_temperature        150.0
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.999
_diffrn_measured_fraction_theta_max  0.999
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_diffrn_source_current             31.0
_diffrn_source_power               1.705
_diffrn_source_voltage             55.0
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.815
_reflns_Friedel_fraction_full      1.000
_reflns_Friedel_fraction_max       1.000
_reflns_number_gt                  1979
_reflns_number_total               2769
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics      'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max           1.168
_refine_diff_density_min           -0.512
_refine_diff_density_rms           0.093
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack     0.0(3)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.078
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       167
_refine_ls_number_reflns           2769
_refine_ls_number_restraints       9
_refine_ls_R_factor_all            0.1064
_refine_ls_R_factor_gt             0.0832
_refine_ls_restrained_S_all        1.078
_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)+(0.1336P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.2167
_refine_ls_wR_factor_ref           0.2346
_refine_special_details
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.0(3)
 0.0(3)
2. 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, All O(H) groups
3. Restrained distances
 S1-C2A \\sim S1-C2
 with sigma of 0.02
 C3-C2A \\sim C3-C2
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
C2A \\sim C2: within 2A with sigma of 0.004 and sigma for terminal atoms of
0.008 within 2A
5. Others
 Sof(H3B)=Sof(C2)=Sof(H2A)=Sof(H2B)=1-FVAR(1)
 Sof(H3A)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C3(H3A), C3(H3B)
6.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C2A(H2AA,H2AB), C2(H2A,H2B)
6.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11)
6.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
6.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
 C1 C 0.0701(12) 0.2974(11) 0.8536(3) 0.0393(14) Uani 1 1 d . . . . .
 C3 C 0.3088(12) 0.6466(13) 0.8740(3) 0.0418(16) Uani 1 1 d D . . . .
 H3A H 0.216770 0.794845 0.883049 0.050 Uiso 0.65(3) 1 calc R U P A 1
 H3B H 0.221022 0.801299 0.868373 0.050 Uiso 0.35(3) 1 calc R U P A 2
 C4 C 0.5543(16) 0.7022(18) 0.8495(4) 0.064(3) Uani 1 1 d . . . . .
 H4A H 0.646084 0.553485 0.843573 0.076 Uiso 1 1 calc R U . . .
 H4B H 0.535470 0.783561 0.804466 0.076 Uiso 1 1 calc R U . . .
 C5 C 0.1007(12) 0.5618(11) 0.7567(3) 0.0407(16) Uani 1 1 d . . . . .
 H5A H 0.074601 0.735461 0.755725 0.049 Uiso 1 1 calc R U . . .
 H5B H -0.056663 0.485802 0.742343 0.049 Uiso 1 1 calc R U . . .
 C6 C 0.2795(12) 0.5012(10) 0.7051(3) 0.0338(14) Uani 1 1 d . . . . .
 C7 C 0.4301(12) 0.3002(12) 0.7113(3) 0.0399(15) Uani 1 1 d . . . . .
 H7 H 0.422078 0.200158 0.750287 0.048 Uiso 1 1 calc R U . . .
 C8 C 0.5880(12) 0.2453(12) 0.6625(3) 0.0397(15) Uani 1 1 d . . . . .
 H8 H 0.686876 0.107685 0.668063 0.048 Uiso 1 1 calc R U . . .
 C9 C 0.6060(13) 0.3879(13) 0.6050(3) 0.0395(15) Uani 1 1 d . . . . .
 C10 C 0.4565(13) 0.5882(12) 0.5982(3) 0.0419(17) Uani 1 1 d . . . . .
 H10 H 0.464006 0.688238 0.559238 0.050 Uiso 1 1 calc R U . . .
 C11 C 0.3011(13) 0.6399(14) 0.6469(3) 0.0434(16) Uani 1 1 d . . . . .
 H11 H 0.202214 0.777458 0.641119 0.052 Uiso 1 1 calc R U . . .
 C12 C 0.9227(15) 0.1513(16) 0.5612(4) 0.0526(19) Uani 1 1 d . . . . .
 H12A H 1.016234 0.141570 0.520397 0.079 Uiso 1 1 calc R U . . .
 H12B H 0.831675 0.003600 0.566145 0.079 Uiso 1 1 calc R U . . .
 H12C H 1.034015 0.175233 0.601975 0.079 Uiso 1 1 calc R U . . .
 N1 N 0.1689(10) 0.4920(10) 0.8267(3) 0.0405(13) Uani 1 1 d . . . . .
 O1 O -0.0604(10) 0.1551(9) 0.8212(3) 0.0525(14) Uani 1 1 d . . . . .
 O2 O 0.6823(11) 0.8484(13) 0.8975(3) 0.072(2) Uani 1 1 d . . . . .
 H2 H 0.787815 0.925902 0.877918 0.108 Uiso 1 1 calc R U . . .
 O3 O 0.7551(9) 0.3474(9) 0.5541(2) 0.0480(13) Uani 1 1 d . . . . .
 S1 S 0.1459(3) 0.2760(3) 0.94244(8) 0.0486(6) Uani 1 1 d D . . . .
 C2A C 0.369(3) 0.507(3) 0.9407(6) 0.052(4) Uani 0.65(3) 1 d D U P A 1
 H2AA H 0.360738 0.611430 0.981143 0.062 Uiso 0.65(3) 1 calc R U P A 1
 H2AB H 0.534532 0.438173 0.941026 0.062 Uiso 0.65(3) 1 calc R U P A 1
 C2 C 0.265(6) 0.577(4) 0.9463(10) 0.051(4) Uani 0.35(3) 1 d D U P A 2
 H2A H 0.146494 0.686347 0.965535 0.062 Uiso 0.35(3) 1 calc R U P A 2
 H2B H 0.419029 0.583685 0.975586 0.062 Uiso 0.35(3) 1 calc R U P A 2


_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 N1 1.348(9) . ?
 C1 O1 1.225(8) . ?
 C1 S1 1.759(6) . ?
 C3 H3A 1.0000 . ?
 C3 H3B 1.0000 . ?
 C3 C4 1.498(11) . ?
 C3 N1 1.452(8) . ?
 C3 C2A 1.540(14) . ?
 C3 C2 1.500(19) . ?
 C4 H4A 0.9900 . ?
 C4 H4B 0.9900 . ?
 C4 O2 1.402(9) . ?
 C5 H5A 0.9900 . ?
 C5 H5B 0.9900 . ?
 C5 C6 1.496(9) . ?
 C5 N1 1.446(8) . ?
 C6 C7 1.405(9) . ?
 C6 C11 1.390(9) . ?
 C7 H7 0.9500 . ?
 C7 C8 1.369(9) . ?
 C8 H8 0.9500 . ?
 C8 C9 1.391(9) . ?
 C9 C10 1.399(10) . ?
 C9 O3 1.351(8) . ?
 C10 H10 0.9500 . ?
 C10 C11 1.355(10) . ?
 C11 H11 0.9500 . ?
 C12 H12A 0.9800 . ?
 C12 H12B 0.9800 . ?
 C12 H12C 0.9800 . ?
 C12 O3 1.441(10) . ?
 O2 H2 0.8400 . ?
 S1 C2A 1.790(12) . ?
 S1 C2 1.82(2) . ?
 C2A H2AA 0.9900 . ?
 C2A H2AB 0.9900 . ?
 C2 H2A 0.9900 . ?
 C2 H2B 0.9900 . ?

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
 N1 C1 S1 111.5(5) . . ?
 O1 C1 N1 124.7(6) . . ?
 O1 C1 S1 123.8(5) . . ?
 C4 C3 H3A 111.2 . . ?
 C4 C3 H3B 102.9 . . ?
 C4 C3 C2A 103.4(8) . . ?
 C4 C3 C2 124.2(14) . . ?
 N1 C3 H3A 111.2 . . ?
 N1 C3 H3B 102.9 . . ?
 N1 C3 C4 111.9(6) . . ?
 N1 C3 C2A 107.7(7) . . ?
 N1 C3 C2 109.3(10) . . ?
 C2A C3 H3A 111.2 . . ?
 C2 C3 H3B 102.9 . . ?
 C3 C4 H4A 109.8 . . ?
 C3 C4 H4B 109.8 . . ?
 H4A C4 H4B 108.2 . . ?
 O2 C4 C3 109.4(6) . . ?
 O2 C4 H4A 109.8 . . ?
 O2 C4 H4B 109.8 . . ?
 H5A C5 H5B 107.4 . . ?
 C6 C5 H5A 108.3 . . ?
 C6 C5 H5B 108.3 . . ?
 N1 C5 H5A 108.3 . . ?
 N1 C5 H5B 108.3 . . ?
 N1 C5 C6 115.7(6) . . ?
 C7 C6 C5 122.5(5) . . ?
 C11 C6 C5 121.2(6) . . ?
 C11 C6 C7 116.3(6) . . ?
 C6 C7 H7 119.3 . . ?
 C8 C7 C6 121.4(6) . . ?
 C8 C7 H7 119.3 . . ?
 C7 C8 H8 119.5 . . ?
 C7 C8 C9 121.0(6) . . ?
 C9 C8 H8 119.5 . . ?
 C8 C9 C10 118.0(6) . . ?
 O3 C9 C8 125.2(7) . . ?
 O3 C9 C10 116.7(6) . . ?
 C9 C10 H10 119.9 . . ?
 C11 C10 C9 120.2(6) . . ?
 C11 C10 H10 119.9 . . ?
 C6 C11 H11 118.5 . . ?
 C10 C11 C6 123.1(7) . . ?
 C10 C11 H11 118.5 . . ?
 H12A C12 H12B 109.5 . . ?
 H12A C12 H12C 109.5 . . ?
 H12B C12 H12C 109.5 . . ?
 O3 C12 H12A 109.5 . . ?
 O3 C12 H12B 109.5 . . ?
 O3 C12 H12C 109.5 . . ?
 C1 N1 C3 116.8(6) . . ?
 C1 N1 C5 120.3(6) . . ?
 C5 N1 C3 122.0(6) . . ?
 C4 O2 H2 109.5 . . ?
 C9 O3 C12 118.4(6) . . ?
 C1 S1 C2A 92.8(4) . . ?
 C1 S1 C2 92.1(7) . . ?
 C3 C2A S1 106.3(7) . . ?
 C3 C2A H2AA 110.5 . . ?
 C3 C2A H2AB 110.5 . . ?
 S1 C2A H2AA 110.5 . . ?
 S1 C2A H2AB 110.5 . . ?
 H2AA C2A H2AB 108.7 . . ?
 C3 C2 S1 106.5(12) . . ?
 C3 C2 H2A 110.4 . . ?
 C3 C2 H2B 110.4 . . ?
 S1 C2 H2A 110.4 . . ?
 S1 C2 H2B 110.4 . . ?
 H2A C2 H2B 108.6 . . ?

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
 C1 S1 C2A C3 19.3(11) . . . . ?
 C1 S1 C2 C3 -17.6(19) . . . . ?
 C4 C3 N1 C1 129.3(8) . . . . ?
 C4 C3 N1 C5 -61.5(9) . . . . ?
 C4 C3 C2A S1 -141.3(9) . . . . ?
 C4 C3 C2 S1 -116.4(14) . . . . ?
 C5 C6 C7 C8 178.4(6) . . . . ?
 C5 C6 C11 C10 -178.4(6) . . . . ?
 C6 C5 N1 C1 -101.9(7) . . . . ?
 C6 C5 N1 C3 89.3(7) . . . . ?
 C6 C7 C8 C9 0.4(9) . . . . ?
 C7 C6 C11 C10 0.1(10) . . . . ?
 C7 C8 C9 C10 -0.5(10) . . . . ?
 C7 C8 C9 O3 -179.6(6) . . . . ?
 C8 C9 C10 C11 0.5(10) . . . . ?
 C8 C9 O3 C12 -4.7(9) . . . . ?
 C9 C10 C11 C6 -0.3(10) . . . . ?
 C10 C9 O3 C12 176.2(6) . . . . ?
 C11 C6 C7 C8 -0.2(9) . . . . ?
 N1 C1 S1 C2A -11.1(8) . . . . ?
 N1 C1 S1 C2 11.6(12) . . . . ?
 N1 C3 C4 O2 -179.1(7) . . . . ?
 N1 C3 C2A S1 -22.6(13) . . . . ?
 N1 C3 C2 S1 19(2) . . . . ?
 N1 C5 C6 C7 31.4(8) . . . . ?
 N1 C5 C6 C11 -150.1(6) . . . . ?
 O1 C1 N1 C3 176.9(7) . . . . ?
 O1 C1 N1 C5 7.5(10) . . . . ?
 O1 C1 S1 C2A 170.3(9) . . . . ?
 O1 C1 S1 C2 -167.0(13) . . . . ?
 O3 C9 C10 C11 179.6(6) . . . . ?
 S1 C1 N1 C3 -1.6(7) . . . . ?
 S1 C1 N1 C5 -171.0(5) . . . . ?
 C2A C3 C4 O2 -63.4(11) . . . . ?
 C2A C3 N1 C1 16.3(11) . . . . ?
 C2A C3 N1 C5 -174.5(10) . . . . ?
 C2 C3 C4 O2 -44.3(16) . . . . ?
 C2 C3 N1 C1 -12.2(17) . . . . ?
 C2 C3 N1 C5 157.0(16) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
loop_
  _twin_individual_id
  _twin_individual_mass_fraction_refined
 1 1.0(3)
 2 0.0(3)

