data_mo_20180619_0m
_audit_creation_date               2018-06-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_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           'C27 H26 Cl N O3 S'
_chemical_formula_sum              'C27 H26 Cl N O3 S'
_chemical_formula_weight           480.00
_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/c 1'
_space_group_name_Hall             '-P 2ybc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'

_cell_length_a                     9.816(4)
_cell_length_b                     17.033(7)
_cell_length_c                     14.307(6)
_cell_angle_alpha                  90
_cell_angle_beta                   98.619(9)
_cell_angle_gamma                  90
_cell_volume                       2364.9(18)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      1359
_cell_measurement_temperature      173
_cell_measurement_theta_max        22.77
_cell_measurement_theta_min        2.39
_shelx_estimated_absorpt_T_max     0.978
_shelx_estimated_absorpt_T_min     0.949
_exptl_absorpt_coefficient_mu      0.280
_exptl_absorpt_correction_T_max    0.7454
_exptl_absorpt_correction_T_min    0.5726
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details    
 'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0833 before and 0.0606 after correction. The Ratio of minimum to maximum transmission is 0.7682. 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      1.348
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               1008
_exptl_crystal_size_max            0.19
_exptl_crystal_size_mid            0.12
_exptl_crystal_size_min            0.08
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0565
_diffrn_reflns_av_unetI/netI       0.0618
_diffrn_reflns_Laue_measured_fraction_full  0.994
_diffrn_reflns_Laue_measured_fraction_max  0.986
_diffrn_reflns_limit_h_max         9
_diffrn_reflns_limit_h_min         -12
_diffrn_reflns_limit_k_max         21
_diffrn_reflns_limit_k_min         -21
_diffrn_reflns_limit_l_max         17
_diffrn_reflns_limit_l_min         -17
_diffrn_reflns_number              15409
_diffrn_reflns_point_group_measured_fraction_full  0.994
_diffrn_reflns_point_group_measured_fraction_max  0.986
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           26.418
_diffrn_reflns_theta_min           1.871
_diffrn_ambient_temperature        173
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.994
_diffrn_measured_fraction_theta_max  0.986
_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                  3447
_reflns_number_total               4799
_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           0.275
_refine_diff_density_min           -0.398
_refine_diff_density_rms           0.066
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.018
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       300
_refine_ls_number_reflns           4799
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0740
_refine_ls_R_factor_gt             0.0488
_refine_ls_restrained_S_all        1.018
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0820P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1308
_refine_ls_wR_factor_ref           0.1469
_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:
 C11(H11), C12(H12), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C8(H8), C15(H15), C16(H16), C18(H18),
 C19(H19), C22(H22), C23(H23), C25(H25), C26(H26)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C27(H27A,H27B,H27C)
;
_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 0.79551(7) 0.33660(4) 0.95738(6) 0.0492(2) Uani 1 1 d . . . . .
 S1 S 0.02131(7) 0.35959(4) 0.65488(4) 0.02949(18) Uani 1 1 d . . . . .
 O1 O 0.06188(18) 0.50272(10) 0.61621(11) 0.0313(4) Uani 1 1 d . . . . .
 O2 O -0.12107(19) 0.38038(12) 0.63332(12) 0.0403(5) Uani 1 1 d . . . . .
 O3 O 0.0688(2) 0.28502(10) 0.62729(12) 0.0402(5) Uani 1 1 d . . . . .
 N1 N 0.1051(2) 0.42355(11) 0.59604(13) 0.0272(5) Uani 1 1 d . . . . .
 C1 C 0.5700(3) 0.45652(16) 0.74881(18) 0.0347(6) Uani 1 1 d . . . . .
 H1 H 0.5766 0.4709 0.6855 0.042 Uiso 1 1 calc R . . . .
 C2 C 0.6751(3) 0.41235(16) 0.79941(19) 0.0378(6) Uani 1 1 d . . . . .
 H2 H 0.7525 0.3968 0.7712 0.045 Uiso 1 1 calc R . . . .
 C3 C 0.6651(3) 0.39137(15) 0.89177(19) 0.0346(6) Uani 1 1 d . . . . .
 C4 C 0.5514(3) 0.41201(15) 0.93218(18) 0.0340(6) Uani 1 1 d . . . . .
 H4 H 0.5436 0.3960 0.9948 0.041 Uiso 1 1 calc R . . . .
 C5 C 0.4483(3) 0.45642(15) 0.88030(16) 0.0331(6) Uani 1 1 d . . . . .
 H5 H 0.3703 0.4711 0.9084 0.040 Uiso 1 1 calc R . . . .
 C6 C 0.4559(3) 0.48019(14) 0.78803(16) 0.0286(5) Uani 1 1 d . . . . .
 C7 C 0.3430(3) 0.52811(14) 0.73493(16) 0.0304(6) Uani 1 1 d . . . . .
 C8 C 0.2820(3) 0.58464(15) 0.77735(18) 0.0382(6) Uani 1 1 d . . . . .
 H8 H 0.3140 0.5934 0.8425 0.046 Uiso 1 1 calc R . . . .
 C9 C 0.1665(3) 0.63616(16) 0.73101(19) 0.0430(7) Uani 1 1 d . . . . .
 H9A H 0.1836 0.6909 0.7528 0.052 Uiso 1 1 calc R . . . .
 H9B H 0.0788 0.6187 0.7505 0.052 Uiso 1 1 calc R . . . .
 C10 C 0.1533(3) 0.63356(15) 0.62370(19) 0.0407(7) Uani 1 1 d . . . . .
 H10A H 0.0620 0.6544 0.5959 0.049 Uiso 1 1 calc R . . . .
 H10B H 0.2248 0.6676 0.6028 0.049 Uiso 1 1 calc R . . . .
 C11 C 0.1691(3) 0.55091(15) 0.58803(17) 0.0333(6) Uani 1 1 d . . . . .
 H11 H 0.1616 0.5512 0.5175 0.040 Uiso 1 1 calc R . . . .
 C12 C 0.3007(3) 0.50923(14) 0.63088(16) 0.0287(6) Uani 1 1 d . . . . .
 H12 H 0.3772 0.5232 0.5949 0.034 Uiso 1 1 calc R . . . .
 C13 C 0.2604(3) 0.42149(14) 0.61361(15) 0.0261(5) Uani 1 1 d . . . . .
 H13 H 0.2932 0.3900 0.6716 0.031 Uiso 1 1 calc R . . . .
 C14 C 0.3145(3) 0.38637(14) 0.52928(16) 0.0257(5) Uani 1 1 d . . . . .
 C15 C 0.4286(3) 0.33782(14) 0.54208(17) 0.0325(6) Uani 1 1 d . . . . .
 H15 H 0.4721 0.3261 0.6044 0.039 Uiso 1 1 calc R . . . .
 C16 C 0.4806(3) 0.30595(16) 0.46551(18) 0.0360(6) Uani 1 1 d . . . . .
 H16 H 0.5603 0.2736 0.4762 0.043 Uiso 1 1 calc R . . . .
 C17 C 0.4183(3) 0.32050(15) 0.37361(17) 0.0327(6) Uani 1 1 d . . . . .
 C18 C 0.3062(3) 0.37091(14) 0.36063(17) 0.0317(6) Uani 1 1 d . . . . .
 H18 H 0.2645 0.3837 0.2982 0.038 Uiso 1 1 calc R . . . .
 C19 C 0.2537(3) 0.40309(15) 0.43667(16) 0.0300(6) Uani 1 1 d . . . . .
 H19 H 0.1758 0.4368 0.4258 0.036 Uiso 1 1 calc R . . . .
 C20 C 0.4667(3) 0.28087(18) 0.28995(19) 0.0455(7) Uani 1 1 d . . . . .
 H20A H 0.4183 0.2308 0.2773 0.068 Uiso 1 1 calc GR . . . .
 H20B H 0.5661 0.2713 0.3040 0.068 Uiso 1 1 calc GR . . . .
 H20C H 0.4471 0.3148 0.2343 0.068 Uiso 1 1 calc GR . . . .
 C21 C 0.0734(3) 0.37142(14) 0.77806(16) 0.0274(5) Uani 1 1 d . . . . .
 C22 C 0.1297(3) 0.30773(16) 0.83004(17) 0.0349(6) Uani 1 1 d . . . . .
 H22 H 0.1434 0.2594 0.7997 0.042 Uiso 1 1 calc R . . . .
 C23 C 0.1659(3) 0.31537(16) 0.92725(17) 0.0367(6) Uani 1 1 d . . . . .
 H23 H 0.2013 0.2713 0.9637 0.044 Uiso 1 1 calc R . . . .
 C24 C 0.1511(3) 0.38642(16) 0.97189(17) 0.0320(6) Uani 1 1 d . . . . .
 C25 C 0.0955(3) 0.44969(15) 0.91785(17) 0.0328(6) Uani 1 1 d . . . . .
 H25 H 0.0857 0.4988 0.9475 0.039 Uiso 1 1 calc R . . . .
 C26 C 0.0542(3) 0.44217(15) 0.82171(16) 0.0300(6) Uani 1 1 d . . . . .
 H26 H 0.0130 0.4852 0.7858 0.036 Uiso 1 1 calc R . . . .
 C27 C 0.1947(4) 0.39430(18) 1.07737(18) 0.0474(8) Uani 1 1 d . . . . .
 H27A H 0.1515 0.3526 1.1100 0.071 Uiso 1 1 calc GR . . . .
 H27B H 0.1657 0.4456 1.0984 0.071 Uiso 1 1 calc GR . . . .
 H27C H 0.2952 0.3898 1.0921 0.071 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 C3 1.740(3) . ?
 S1 O2 1.430(2) . ?
 S1 O3 1.4288(19) . ?
 S1 N1 1.667(2) . ?
 S1 C21 1.771(2) . ?
 O1 N1 1.455(3) . ?
 O1 C11 1.439(3) . ?
 N1 C13 1.508(3) . ?
 C1 H1 0.9500 . ?
 C1 C2 1.389(4) . ?
 C1 C6 1.386(4) . ?
 C2 H2 0.9500 . ?
 C2 C3 1.386(4) . ?
 C3 C4 1.378(4) . ?
 C4 H4 0.9500 . ?
 C4 C5 1.386(4) . ?
 C5 H5 0.9500 . ?
 C5 C6 1.393(3) . ?
 C6 C7 1.490(3) . ?
 C7 C8 1.328(4) . ?
 C7 C12 1.519(3) . ?
 C8 H8 0.9500 . ?
 C8 C9 1.507(4) . ?
 C9 H9A 0.9900 . ?
 C9 H9B 0.9900 . ?
 C9 C10 1.522(4) . ?
 C10 H10A 0.9900 . ?
 C10 H10B 0.9900 . ?
 C10 C11 1.513(4) . ?
 C11 H11 1.0000 . ?
 C11 C12 1.520(4) . ?
 C12 H12 1.0000 . ?
 C12 C13 1.556(3) . ?
 C13 H13 1.0000 . ?
 C13 C14 1.512(3) . ?
 C14 C15 1.382(4) . ?
 C14 C19 1.398(3) . ?
 C15 H15 0.9500 . ?
 C15 C16 1.387(4) . ?
 C16 H16 0.9500 . ?
 C16 C17 1.387(4) . ?
 C17 C18 1.386(4) . ?
 C17 C20 1.511(3) . ?
 C18 H18 0.9500 . ?
 C18 C19 1.385(3) . ?
 C19 H19 0.9500 . ?
 C20 H20A 0.9800 . ?
 C20 H20B 0.9800 . ?
 C20 H20C 0.9800 . ?
 C21 C22 1.383(3) . ?
 C21 C26 1.383(3) . ?
 C22 H22 0.9500 . ?
 C22 C23 1.389(4) . ?
 C23 H23 0.9500 . ?
 C23 C24 1.386(4) . ?
 C24 C25 1.389(4) . ?
 C24 C27 1.512(3) . ?
 C25 H25 0.9500 . ?
 C25 C26 1.380(3) . ?
 C26 H26 0.9500 . ?
 C27 H27A 0.9800 . ?
 C27 H27B 0.9800 . ?
 C27 H27C 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 N1 105.64(11) . . ?
 O2 S1 C21 108.27(11) . . ?
 O3 S1 O2 120.64(12) . . ?
 O3 S1 N1 103.60(11) . . ?
 O3 S1 C21 108.57(11) . . ?
 N1 S1 C21 109.71(11) . . ?
 C11 O1 N1 103.04(17) . . ?
 O1 N1 S1 108.95(14) . . ?
 O1 N1 C13 107.82(17) . . ?
 C13 N1 S1 117.62(15) . . ?
 C2 C1 H1 119.0 . . ?
 C6 C1 H1 119.0 . . ?
 C6 C1 C2 121.9(2) . . ?
 C1 C2 H2 120.5 . . ?
 C3 C2 C1 118.9(3) . . ?
 C3 C2 H2 120.5 . . ?
 C2 C3 Cl1 120.1(2) . . ?
 C4 C3 Cl1 119.2(2) . . ?
 C4 C3 C2 120.8(3) . . ?
 C3 C4 H4 120.4 . . ?
 C3 C4 C5 119.1(2) . . ?
 C5 C4 H4 120.4 . . ?
 C4 C5 H5 119.1 . . ?
 C4 C5 C6 121.8(3) . . ?
 C6 C5 H5 119.1 . . ?
 C1 C6 C5 117.4(2) . . ?
 C1 C6 C7 122.5(2) . . ?
 C5 C6 C7 120.1(2) . . ?
 C6 C7 C12 117.2(2) . . ?
 C8 C7 C6 121.1(2) . . ?
 C8 C7 C12 121.7(2) . . ?
 C7 C8 H8 117.2 . . ?
 C7 C8 C9 125.6(2) . . ?
 C9 C8 H8 117.2 . . ?
 C8 C9 H9A 109.3 . . ?
 C8 C9 H9B 109.3 . . ?
 C8 C9 C10 111.8(2) . . ?
 H9A C9 H9B 107.9 . . ?
 C10 C9 H9A 109.3 . . ?
 C10 C9 H9B 109.3 . . ?
 C9 C10 H10A 109.3 . . ?
 C9 C10 H10B 109.3 . . ?
 H10A C10 H10B 107.9 . . ?
 C11 C10 C9 111.7(2) . . ?
 C11 C10 H10A 109.3 . . ?
 C11 C10 H10B 109.3 . . ?
 O1 C11 C10 108.7(2) . . ?
 O1 C11 H11 109.8 . . ?
 O1 C11 C12 103.52(19) . . ?
 C10 C11 H11 109.8 . . ?
 C10 C11 C12 115.0(2) . . ?
 C12 C11 H11 109.8 . . ?
 C7 C12 C11 112.8(2) . . ?
 C7 C12 H12 109.8 . . ?
 C7 C12 C13 112.61(19) . . ?
 C11 C12 H12 109.8 . . ?
 C11 C12 C13 101.76(19) . . ?
 C13 C12 H12 109.8 . . ?
 N1 C13 C12 103.35(19) . . ?
 N1 C13 H13 110.0 . . ?
 N1 C13 C14 110.05(18) . . ?
 C12 C13 H13 110.0 . . ?
 C14 C13 C12 113.29(19) . . ?
 C14 C13 H13 110.0 . . ?
 C15 C14 C13 120.3(2) . . ?
 C15 C14 C19 118.0(2) . . ?
 C19 C14 C13 121.6(2) . . ?
 C14 C15 H15 119.5 . . ?
 C14 C15 C16 121.1(2) . . ?
 C16 C15 H15 119.5 . . ?
 C15 C16 H16 119.4 . . ?
 C17 C16 C15 121.1(2) . . ?
 C17 C16 H16 119.4 . . ?
 C16 C17 C20 121.7(2) . . ?
 C18 C17 C16 117.8(2) . . ?
 C18 C17 C20 120.5(2) . . ?
 C17 C18 H18 119.3 . . ?
 C19 C18 C17 121.4(2) . . ?
 C19 C18 H18 119.3 . . ?
 C14 C19 H19 119.7 . . ?
 C18 C19 C14 120.5(2) . . ?
 C18 C19 H19 119.7 . . ?
 C17 C20 H20A 109.5 . . ?
 C17 C20 H20B 109.5 . . ?
 C17 C20 H20C 109.5 . . ?
 H20A C20 H20B 109.5 . . ?
 H20A C20 H20C 109.5 . . ?
 H20B C20 H20C 109.5 . . ?
 C22 C21 S1 118.58(19) . . ?
 C22 C21 C26 120.7(2) . . ?
 C26 C21 S1 120.65(18) . . ?
 C21 C22 H22 120.4 . . ?
 C21 C22 C23 119.1(2) . . ?
 C23 C22 H22 120.4 . . ?
 C22 C23 H23 119.5 . . ?
 C24 C23 C22 121.0(2) . . ?
 C24 C23 H23 119.5 . . ?
 C23 C24 C25 118.7(2) . . ?
 C23 C24 C27 120.3(2) . . ?
 C25 C24 C27 121.0(2) . . ?
 C24 C25 H25 119.5 . . ?
 C26 C25 C24 121.0(2) . . ?
 C26 C25 H25 119.5 . . ?
 C21 C26 H26 120.3 . . ?
 C25 C26 C21 119.4(2) . . ?
 C25 C26 H26 120.3 . . ?
 C24 C27 H27A 109.5 . . ?
 C24 C27 H27B 109.5 . . ?
 C24 C27 H27C 109.5 . . ?
 H27A C27 H27B 109.5 . . ?
 H27A C27 H27C 109.5 . . ?
 H27B C27 H27C 109.5 . . ?


_olex2_submission_special_instructions  'No special instructions were received'
