data_mo_20180101-134-2_0m
_audit_creation_date               2018-01-30
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.01.22 svn.r3481 for OlexSys, GUI svn.r5457)
;
_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           'C26 H24 Cl N O3 S'
_chemical_formula_sum              'C26 H24 Cl N O3 S'
_chemical_formula_weight           465.97
_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'
 'Cl' 'Cl' 0.1484 0.1585 '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             14
_space_group_name_H-M_alt          'P 1 21/n 1'
_space_group_name_Hall             '-P 2yn'
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                     6.0404(10)
_cell_length_b                     18.307(3)
_cell_length_c                     20.483(3)
_cell_angle_alpha                  90
_cell_angle_beta                   96.951(4)
_cell_angle_gamma                  90
_cell_volume                       2248.4(7)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      3412
_cell_measurement_temperature      173
_cell_measurement_theta_max        26.91
_cell_measurement_theta_min        2.50
_shelx_estimated_absorpt_T_max     0.966
_shelx_estimated_absorpt_T_min     0.923
_exptl_absorpt_coefficient_mu      0.292
_exptl_absorpt_correction_T_max    0.7456
_exptl_absorpt_correction_T_min    0.6783
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details    
 'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0886 before and 0.0632 after correction. The Ratio of minimum to maximum transmission is 0.9097. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.377
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               976
_exptl_crystal_size_max            0.28
_exptl_crystal_size_mid            0.15
_exptl_crystal_size_min            0.12
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0750
_diffrn_reflns_av_unetI/netI       0.0790
_diffrn_reflns_Laue_measured_fraction_full  0.999
_diffrn_reflns_Laue_measured_fraction_max  0.995
_diffrn_reflns_limit_h_max         7
_diffrn_reflns_limit_h_min         -7
_diffrn_reflns_limit_k_max         23
_diffrn_reflns_limit_k_min         -23
_diffrn_reflns_limit_l_max         26
_diffrn_reflns_limit_l_min         -26
_diffrn_reflns_number              20191
_diffrn_reflns_point_group_measured_fraction_full  0.999
_diffrn_reflns_point_group_measured_fraction_max  0.995
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           27.545
_diffrn_reflns_theta_min           1.497
_diffrn_ambient_temperature        173
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.999
_diffrn_measured_fraction_theta_max  0.995
_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_standards_number           0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  3140
_reflns_number_total               5160
_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         'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.299
_refine_diff_density_min           -0.386
_refine_diff_density_rms           0.058
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     0.994
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       290
_refine_ls_number_reflns           5160
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0988
_refine_ls_R_factor_gt             0.0523
_refine_ls_restrained_S_all        0.994
_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)+(0.0663P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1226
_refine_ls_wR_factor_ref           0.1453
_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 Ternary CH refined with riding coordinates:
 C14(H14), C13(H13), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C26(H26), C20(H20), C22(H22), C23(H23), C25(H25), C11(H11), C4(H4),
 C17(H17), C19(H19), C3(H3), C6(H6), C18(H18), C7(H7)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
 Cl1 Cl 1.06941(12) -0.03741(4) 0.58031(4) 0.0465(2) Uani 1 1 d . . . . .
 S1 S 0.10585(12) 0.41688(4) 0.69088(4) 0.0452(2) Uani 1 1 d . . . . .
 O3 O 0.2465(3) 0.31319(9) 0.62387(8) 0.0334(4) Uani 1 1 d . . . . .
 O2 O -0.0939(3) 0.41190(12) 0.64672(12) 0.0612(6) Uani 1 1 d . . . . .
 O1 O 0.0983(4) 0.43090(12) 0.75939(11) 0.0620(7) Uani 1 1 d . . . . .
 N1 N 0.2239(4) 0.33425(11) 0.69102(11) 0.0367(5) Uani 1 1 d . . . . .
 C14 C 0.4837(4) 0.30547(13) 0.62064(11) 0.0268(5) Uani 1 1 d . . . . .
 H14 H 0.5486 0.3553 0.6169 0.032 Uiso 1 1 calc R . . . .
 C15 C 0.5125(4) 0.26369(12) 0.55913(11) 0.0261(5) Uani 1 1 d . . . . .
 C21 C 0.6582(4) 0.13809(13) 0.66577(11) 0.0275(5) Uani 1 1 d . . . . .
 C12 C 0.5332(4) 0.19315(13) 0.70032(12) 0.0289(6) Uani 1 1 d . . . . .
 C13 C 0.5716(4) 0.27424(13) 0.68835(11) 0.0285(6) Uani 1 1 d . . . . .
 H13 H 0.7349 0.2847 0.6974 0.034 Uiso 1 1 calc R . . . .
 C16 C 0.3521(4) 0.21546(13) 0.53074(12) 0.0329(6) Uani 1 1 d . . . . .
 H16 H 0.2186 0.2086 0.5502 0.040 Uiso 1 1 calc R . . . .
 C26 C 0.5794(4) 0.06680(14) 0.65645(13) 0.0362(6) Uani 1 1 d . . . . .
 H26 H 0.4370 0.0548 0.6687 0.043 Uiso 1 1 calc R . . . .
 C20 C 0.7048(4) 0.27425(15) 0.52919(12) 0.0353(6) Uani 1 1 d . . . . .
 H20 H 0.8149 0.3079 0.5475 0.042 Uiso 1 1 calc R . . . .
 C22 C 0.8663(4) 0.15374(14) 0.64526(12) 0.0321(6) Uani 1 1 d . . . . .
 H22 H 0.9240 0.2020 0.6498 0.038 Uiso 1 1 calc R . . . .
 C23 C 0.9886(4) 0.10021(14) 0.61853(13) 0.0353(6) Uani 1 1 d . . . . .
 H23 H 1.1291 0.1120 0.6049 0.042 Uiso 1 1 calc R . . . .
 C24 C 0.9085(4) 0.02965(13) 0.61139(12) 0.0329(6) Uani 1 1 d . . . . .
 C5 C 0.2817(4) 0.48053(14) 0.65934(14) 0.0360(6) Uani 1 1 d . . . . .
 C25 C 0.7019(4) 0.01305(15) 0.62999(14) 0.0394(7) Uani 1 1 d . . . . .
 H25 H 0.6444 -0.0352 0.6246 0.047 Uiso 1 1 calc R . . . .
 C11 C 0.4026(4) 0.17146(15) 0.74470(13) 0.0368(6) Uani 1 1 d . . . . .
 H11 H 0.3787 0.1204 0.7483 0.044 Uiso 1 1 calc R . . . .
 C8 C 0.4462(4) 0.32427(14) 0.73158(12) 0.0358(6) Uani 1 1 d . . . . .
 H8 H 0.5244 0.3724 0.7377 0.043 Uiso 1 1 calc R . . . .
 C4 C 0.4471(5) 0.51478(15) 0.70153(14) 0.0396(7) Uani 1 1 d . . . . .
 H4 H 0.4614 0.5056 0.7475 0.048 Uiso 1 1 calc R . . . .
 C17 C 0.3836(5) 0.17738(15) 0.47461(14) 0.0433(7) Uani 1 1 d . . . . .
 H17 H 0.2727 0.1443 0.4557 0.052 Uiso 1 1 calc R . . . .
 C19 C 0.7365(5) 0.23583(17) 0.47270(13) 0.0436(7) Uani 1 1 d . . . . .
 H19 H 0.8684 0.2430 0.4526 0.052 Uiso 1 1 calc R . . . .
 C2 C 0.5729(5) 0.57683(15) 0.60879(16) 0.0454(7) Uani 1 1 d . . . . .
 C3 C 0.5902(5) 0.56235(15) 0.67556(15) 0.0441(7) Uani 1 1 d . . . . .
 H3 H 0.7037 0.5858 0.7042 0.053 Uiso 1 1 calc R . . . .
 C6 C 0.2567(5) 0.49537(16) 0.59271(15) 0.0471(8) Uani 1 1 d . . . . .
 H6 H 0.1412 0.4728 0.5641 0.056 Uiso 1 1 calc R . . . .
 C18 C 0.5769(5) 0.18729(16) 0.44581(14) 0.0439(7) Uani 1 1 d . . . . .
 H18 H 0.5995 0.1606 0.4074 0.053 Uiso 1 1 calc R . . . .
 C7 C 0.4024(5) 0.54350(17) 0.56847(16) 0.0519(8) Uani 1 1 d . . . . .
 H7 H 0.3850 0.5540 0.5227 0.062 Uiso 1 1 calc R . . . .
 C9 C 0.4127(6) 0.29258(16) 0.79766(13) 0.0492(8) Uani 1 1 d . . . . .
 H9A H 0.3252 0.3271 0.8215 0.059 Uiso 1 1 calc R . . . .
 H9B H 0.5593 0.2854 0.8241 0.059 Uiso 1 1 calc R . . . .
 C10 C 0.2906(5) 0.21988(16) 0.78921(14) 0.0486(8) Uani 1 1 d . . . . .
 H10A H 0.2904 0.1960 0.8326 0.058 Uiso 1 1 calc R . . . .
 H10B H 0.1339 0.2282 0.7704 0.058 Uiso 1 1 calc R . . . .
 C1 C 0.7351(6) 0.62714(19) 0.5815(2) 0.0695(10) Uani 1 1 d . . . . .
 H1A H 0.6952 0.6779 0.5897 0.104 Uiso 1 1 calc GR . . . .
 H1B H 0.7300 0.6191 0.5340 0.104 Uiso 1 1 calc GR . . . .
 H1C H 0.8860 0.6172 0.6030 0.104 Uiso 1 1 calc GR . . . .


_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
 Cl1 C24 1.734(3) . ?
 S1 O2 1.421(2) . ?
 S1 O1 1.433(2) . ?
 S1 N1 1.672(2) . ?
 S1 C5 1.752(3) . ?
 O3 N1 1.451(3) . ?
 O3 C14 1.449(3) . ?
 N1 C8 1.502(3) . ?
 C14 H14 1.0000 . ?
 C14 C15 1.502(3) . ?
 C14 C13 1.534(3) . ?
 C15 C16 1.386(3) . ?
 C15 C20 1.391(3) . ?
 C21 C12 1.489(3) . ?
 C21 C26 1.394(3) . ?
 C21 C22 1.402(3) . ?
 C12 C13 1.527(3) . ?
 C12 C11 1.334(3) . ?
 C13 H13 1.0000 . ?
 C13 C8 1.536(3) . ?
 C16 H16 0.9500 . ?
 C16 C17 1.378(4) . ?
 C26 H26 0.9500 . ?
 C26 C25 1.381(4) . ?
 C20 H20 0.9500 . ?
 C20 C19 1.387(4) . ?
 C22 H22 0.9500 . ?
 C22 C23 1.380(3) . ?
 C23 H23 0.9500 . ?
 C23 C24 1.381(3) . ?
 C24 C25 1.382(4) . ?
 C5 C4 1.389(4) . ?
 C5 C6 1.382(4) . ?
 C25 H25 0.9500 . ?
 C11 H11 0.9500 . ?
 C11 C10 1.491(4) . ?
 C8 H8 1.0000 . ?
 C8 C9 1.509(4) . ?
 C4 H4 0.9500 . ?
 C4 C3 1.378(4) . ?
 C17 H17 0.9500 . ?
 C17 C18 1.382(4) . ?
 C19 H19 0.9500 . ?
 C19 C18 1.376(4) . ?
 C2 C3 1.385(4) . ?
 C2 C7 1.382(4) . ?
 C2 C1 1.501(4) . ?
 C3 H3 0.9500 . ?
 C6 H6 0.9500 . ?
 C6 C7 1.379(4) . ?
 C18 H18 0.9500 . ?
 C7 H7 0.9500 . ?
 C9 H9A 0.9900 . ?
 C9 H9B 0.9900 . ?
 C9 C10 1.521(4) . ?
 C10 H10A 0.9900 . ?
 C10 H10B 0.9900 . ?
 C1 H1A 0.9800 . ?
 C1 H1B 0.9800 . ?
 C1 H1C 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
 O2 S1 O1 120.67(14) . . ?
 O2 S1 N1 105.79(12) . . ?
 O2 S1 C5 108.30(14) . . ?
 O1 S1 N1 102.97(13) . . ?
 O1 S1 C5 109.55(13) . . ?
 N1 S1 C5 108.94(11) . . ?
 C14 O3 N1 106.04(17) . . ?
 O3 N1 S1 109.14(16) . . ?
 O3 N1 C8 108.16(17) . . ?
 C8 N1 S1 117.61(16) . . ?
 O3 C14 H14 108.3 . . ?
 O3 C14 C15 107.68(19) . . ?
 O3 C14 C13 103.36(18) . . ?
 C15 C14 H14 108.3 . . ?
 C15 C14 C13 120.4(2) . . ?
 C13 C14 H14 108.3 . . ?
 C16 C15 C14 122.0(2) . . ?
 C16 C15 C20 118.8(2) . . ?
 C20 C15 C14 119.1(2) . . ?
 C26 C21 C12 121.0(2) . . ?
 C26 C21 C22 117.0(2) . . ?
 C22 C21 C12 121.9(2) . . ?
 C21 C12 C13 119.1(2) . . ?
 C11 C12 C21 119.9(2) . . ?
 C11 C12 C13 120.8(2) . . ?
 C14 C13 H13 108.8 . . ?
 C14 C13 C8 99.10(19) . . ?
 C12 C13 C14 117.7(2) . . ?
 C12 C13 H13 108.8 . . ?
 C12 C13 C8 113.09(19) . . ?
 C8 C13 H13 108.8 . . ?
 C15 C16 H16 119.6 . . ?
 C17 C16 C15 120.8(2) . . ?
 C17 C16 H16 119.6 . . ?
 C21 C26 H26 119.0 . . ?
 C25 C26 C21 122.0(2) . . ?
 C25 C26 H26 119.0 . . ?
 C15 C20 H20 119.9 . . ?
 C19 C20 C15 120.3(3) . . ?
 C19 C20 H20 119.9 . . ?
 C21 C22 H22 119.5 . . ?
 C23 C22 C21 121.1(2) . . ?
 C23 C22 H22 119.5 . . ?
 C22 C23 H23 119.7 . . ?
 C22 C23 C24 120.6(2) . . ?
 C24 C23 H23 119.7 . . ?
 C23 C24 Cl1 119.8(2) . . ?
 C23 C24 C25 119.5(2) . . ?
 C25 C24 Cl1 120.7(2) . . ?
 C4 C5 S1 119.6(2) . . ?
 C6 C5 S1 119.8(2) . . ?
 C6 C5 C4 120.7(3) . . ?
 C26 C25 C24 119.7(2) . . ?
 C26 C25 H25 120.1 . . ?
 C24 C25 H25 120.1 . . ?
 C12 C11 H11 117.0 . . ?
 C12 C11 C10 126.1(2) . . ?
 C10 C11 H11 117.0 . . ?
 N1 C8 C13 102.93(19) . . ?
 N1 C8 H8 109.8 . . ?
 N1 C8 C9 109.6(2) . . ?
 C13 C8 H8 109.8 . . ?
 C9 C8 C13 114.7(2) . . ?
 C9 C8 H8 109.8 . . ?
 C5 C4 H4 120.6 . . ?
 C3 C4 C5 118.9(3) . . ?
 C3 C4 H4 120.6 . . ?
 C16 C17 H17 120.0 . . ?
 C16 C17 C18 119.9(3) . . ?
 C18 C17 H17 120.0 . . ?
 C20 C19 H19 120.0 . . ?
 C18 C19 C20 120.0(3) . . ?
 C18 C19 H19 120.0 . . ?
 C3 C2 C1 120.7(3) . . ?
 C7 C2 C3 117.9(3) . . ?
 C7 C2 C1 121.4(3) . . ?
 C4 C3 C2 121.8(3) . . ?
 C4 C3 H3 119.1 . . ?
 C2 C3 H3 119.1 . . ?
 C5 C6 H6 120.6 . . ?
 C7 C6 C5 118.9(3) . . ?
 C7 C6 H6 120.6 . . ?
 C17 C18 H18 120.0 . . ?
 C19 C18 C17 120.1(3) . . ?
 C19 C18 H18 120.0 . . ?
 C2 C7 H7 119.0 . . ?
 C6 C7 C2 121.9(3) . . ?
 C6 C7 H7 119.0 . . ?
 C8 C9 H9A 109.5 . . ?
 C8 C9 H9B 109.5 . . ?
 C8 C9 C10 110.5(2) . . ?
 H9A C9 H9B 108.1 . . ?
 C10 C9 H9A 109.5 . . ?
 C10 C9 H9B 109.5 . . ?
 C11 C10 C9 109.9(2) . . ?
 C11 C10 H10A 109.7 . . ?
 C11 C10 H10B 109.7 . . ?
 C9 C10 H10A 109.7 . . ?
 C9 C10 H10B 109.7 . . ?
 H10A C10 H10B 108.2 . . ?
 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 . . ?

_olex2_submission_special_instructions  'No special instructions were received'
