data_global
_audit_creation_date                               2015-08-04
_audit_creation_method                            'by CrystalStructure 4.1'
_audit_update_record                               ?

#==============================================================================
# PROCESSING SUMMARY (IUCr Office Use Only)

_journal_date_recd_electronic                      ?
_journal_date_from_coeditor                        ?
_journal_date_accepted                             ?
_journal_coeditor_code                             ?

#==============================================================================
# SUBMISSION DETAILS

_publ_contact_author_name                         'ENTER NAME'
_publ_contact_author_email                        'ENTER EMAIL ADDRESS'
_publ_contact_author_fax                          'ENTER FAX NUMBER'
_publ_contact_author_phone                        'ENTER PHONE NUMBER'
_publ_contact_letter
;
    ENTER TEXT OF LETTER
;
_publ_requested_journal                           'ENTER JOURNAL NAME HERE'

_publ_requested_coeditor_name                      ?

#==============================================================================
# TITLE AND AUTHOR LIST

_publ_section_title
;
    ENTER SECTION TITLE
;
_publ_section_title_footnote
;
    ENTER FOOTNOTE TO TITLE OF PAPER
;
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
' FIRST AUTHORS NAME '
;
  FIRST AUTHORS FOOTNOTES
;
;
  FIRST AUTHORS ADDRESS
;
_publ_section_synopsis
;
    ENTER SYNOPSIS
;

#==============================================================================
# TEXT

_publ_section_abstract
;
    ENTER ABSTRACT
;
_publ_section_comment
;
    ENTER TEXT
;
_publ_section_references
;
    ENTER OTHER REFERENCES

    Rigaku (2014). CrystalStructure. Version 4.1. 
    Rigaku Corporation, Tokyo, Japan.

    Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., 
    Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. and Spagna R.
    (2005). J. Appl. Cryst. 38, 381-388.
    SIR2004

    Sheldrick, G.M. (1997). SHELXL97. University of Gottingen, Germany.

    Rigaku (1998). REQAB. 
    Rigaku Corporation, Tokyo, Japan.

;
_publ_section_figure_captions
;
    ENTER FIGURE CAPTIONS
;
_publ_section_exptl_prep
;
    ENTER COMPOUND PREPARATION DETAILS
;
_publ_section_exptl_refinement
;
    ENTER SPECIAL DETAILS OF THE REFINEMENT
;

#==============================================================================
data_User-defined

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum                             'C18 H18 N2 O2 S'
_chemical_formula_moiety                          'C18 H18 N2 O2 S'
_chemical_formula_weight                           326.41
_chemical_melting_point                            ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system                        monoclinic
_space_group_name_H-M_alt                         'P 1 21/n 1'
_space_group_name_Hall                            '-P 2yn'
_space_group_IT_number                             14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1   '+X,+Y,+Z'
2   '1/2-X,1/2+Y,1/2-Z'
3   '-X,-Y,-Z'
4   '1/2+X,1/2-Y,1/2+Z'
#------------------------------------------------------------------------------
_cell_length_a                                     9.4551(13)
_cell_length_b                                     12.9619(18)
_cell_length_c                                     13.7159(19)
_cell_angle_alpha                                  90.0000
_cell_angle_beta                                   106.971(8)
_cell_angle_gamma                                  90.0000
_cell_volume                                       1607.8(4)
_cell_formula_units_Z                              4
_cell_measurement_reflns_used                      14355
_cell_measurement_theta_min                        3.09
_cell_measurement_theta_max                        27.55
_cell_measurement_temperature                      173
#------------------------------------------------------------------------------
_exptl_crystal_description                         prism
_exptl_crystal_colour                              red
_exptl_crystal_size_max                            0.280
_exptl_crystal_size_mid                            0.220
_exptl_crystal_size_min                            0.160
_exptl_crystal_density_diffrn                      1.348
_exptl_crystal_density_meas                        ?
_exptl_crystal_density_method                     'not measured'
_exptl_crystal_F_000                               688.00
_exptl_absorpt_coefficient_mu                      0.212
_exptl_absorpt_correction_type                     multi-scan
_exptl_absorpt_process_details                    'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min                    0.753
_exptl_absorpt_correction_T_max                    0.967

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature                        173
_diffrn_radiation_type                            'Mo K\a'
_diffrn_radiation_wavelength                       0.71075
_diffrn_measurement_device_type                   'Rigaku XtaLAB mini'
_diffrn_measurement_method                         ω
_diffrn_detector_area_resol_mean                   6.849
_diffrn_reflns_number                              16542
_diffrn_reflns_av_R_equivalents                    0.0453
_diffrn_reflns_theta_max                           27.485
_diffrn_reflns_theta_min                           3.087
_diffrn_reflns_theta_full                          25.242
_diffrn_measured_fraction_theta_max                0.999
_diffrn_measured_fraction_theta_full               0.998
_diffrn_reflns_Laue_measured_fraction_max          0.999
_diffrn_reflns_Laue_measured_fraction_full         0.998
_diffrn_reflns_point_group_measured_fraction_max   0.999
_diffrn_reflns_point_group_measured_fraction_full  0.998
_diffrn_reflns_limit_h_min                        -12
_diffrn_reflns_limit_h_max                         12
_diffrn_reflns_limit_k_min                        -16
_diffrn_reflns_limit_k_max                         16
_diffrn_reflns_limit_l_min                        -17
_diffrn_reflns_limit_l_max                         17
_diffrn_standards_number                           0
_diffrn_standards_interval_count                   .
_diffrn_standards_decay_%                          ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total                               3682
_reflns_number_gt                                  2988
_reflns_threshold_expression                       F²>2.0σ(F²)
_refine_ls_structure_factor_coef                   Fsqd
_refine_ls_R_factor_all                            0.0564
_refine_ls_R_factor_gt                             0.0420
_refine_ls_wR_factor_ref                           0.1014
_refine_ls_wR_factor_gt                            0.0947
_refine_ls_number_restraints                       0
_refine_ls_hydrogen_treatment                      constr
_refine_ls_number_reflns                           3682
_refine_ls_number_parameters                       211
_refine_ls_goodness_of_fit_ref                     1.041
_refine_ls_weighting_scheme                        calc
_refine_ls_weighting_details
           'w = 1/[σ²(Fo²)+(0.0406P)²+0.7722P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens                     geom
_atom_sites_solution_primary                       direct
_atom_sites_solution_secondary                     difmap
_refine_ls_shift/su_max                            0.001
_refine_diff_density_max                           0.35
_refine_diff_density_min                          -0.27
_refine_ls_extinction_method                       none
_refine_ls_extinction_coef                         ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'H' 'H'  0.0000 0.0000 
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
  'N' 'N'  0.0061 0.0033 
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'O' 'O'  0.0106 0.0060 
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'S' 'S'  0.1246 0.1234 
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.60457(4) 1.00164(3) 0.40488(3) 0.02351(12) Uani 1 1 d . . . . .
O1 O 0.10797(13) 1.08441(8) 0.07190(9) 0.0278(3) Uani 1 1 d . . . . .
O2 O 0.10202(13) 0.91394(9) 0.09887(9) 0.0296(3) Uani 1 1 d . . . . .
H2 H 0.0302 0.9169 0.0457 0.035 Uiso 1 1 calc R U . . .
N1 N 0.38165(18) 1.19682(12) 0.25785(13) 0.0367(4) Uani 1 1 d . . . . .
N2 N 1.21536(17) 1.02443(12) 0.81418(12) 0.0331(4) Uani 1 1 d . . . . .
C1 C 0.15703(18) 1.00664(12) 0.12235(12) 0.0219(3) Uani 1 1 d . . . . .
C2 C 0.28582(17) 1.01189(12) 0.21297(12) 0.0218(3) Uani 1 1 d . . . . .
C3 C 0.34199(18) 1.11398(13) 0.23874(13) 0.0245(4) Uani 1 1 d . . . . .
C4 C 0.34074(18) 0.92559(12) 0.26783(12) 0.0231(3) Uani 1 1 d . . . . .
H4 H 0.2843 0.8649 0.2456 0.028 Uiso 1 1 calc R U . . .
C5 C 0.46741(18) 0.91100(12) 0.35221(12) 0.0235(3) Uani 1 1 d . . . . .
C6 C 0.5006(2) 0.81848(13) 0.40395(13) 0.0287(4) Uani 1 1 d . . . . .
H6 H 0.4398 0.7590 0.3865 0.034 Uiso 1 1 calc R U . . .
C7 C 0.63125(19) 0.82037(13) 0.48390(13) 0.0281(4) Uani 1 1 d . . . . .
H7 H 0.6675 0.7627 0.5266 0.034 Uiso 1 1 calc R U . . .
C8 C 0.70311(18) 0.91469(12) 0.49498(12) 0.0229(3) Uani 1 1 d . . . . .
C9 C 0.83909(18) 0.94393(13) 0.57271(12) 0.0231(3) Uani 1 1 d . . . . .
C10 C 0.89468(19) 1.04481(14) 0.58423(13) 0.0282(4) Uani 1 1 d . . . . .
H10 H 0.8457 1.0962 0.5370 0.034 Uiso 1 1 calc R U . . .
C11 C 1.01800(19) 1.07158(14) 0.66185(13) 0.0300(4) Uani 1 1 d . . . . .
H11 H 1.0523 1.1408 0.6668 0.036 Uiso 1 1 calc R U . . .
C12 C 1.09466(18) 0.99881(13) 0.73415(13) 0.0262(4) Uani 1 1 d . . . . .
C13 C 1.04058(18) 0.89683(13) 0.72171(13) 0.0279(4) Uani 1 1 d . . . . .
H13 H 1.0902 0.8450 0.7682 0.033 Uiso 1 1 calc R U . . .
C14 C 0.91695(18) 0.87086(13) 0.64324(13) 0.0259(4) Uani 1 1 d . . . . .
H14 H 0.8837 0.8013 0.6369 0.031 Uiso 1 1 calc R U . . .
C15 C 1.2897(2) 1.12408(15) 0.82038(15) 0.0337(4) Uani 1 1 d . . . . .
H15A H 1.2744 1.1509 0.7505 0.040 Uiso 1 1 calc R U . . .
H15B H 1.3973 1.1138 0.8513 0.040 Uiso 1 1 calc R U . . .
C16 C 1.2362(2) 1.20406(15) 0.88210(16) 0.0381(4) Uani 1 1 d . . . . .
H16A H 1.1300 1.2157 0.8515 0.046 Uiso 1 1 calc R U . . .
H16B H 1.2897 1.2689 0.8825 0.046 Uiso 1 1 calc R U . . .
H16C H 1.2543 1.1793 0.9522 0.046 Uiso 1 1 calc R U . . .
C17 C 1.2713(2) 0.95446(15) 0.90140(14) 0.0344(4) Uani 1 1 d . . . . .
H17A H 1.1881 0.9125 0.9098 0.041 Uiso 1 1 calc R U . . .
H17B H 1.3101 0.9961 0.9640 0.041 Uiso 1 1 calc R U . . .
C18 C 1.3918(2) 0.88301(19) 0.89011(18) 0.0501(6) Uani 1 1 d . . . . .
H18A H 1.4774 0.9238 0.8866 0.060 Uiso 1 1 calc R U . . .
H18B H 1.3550 0.8424 0.8275 0.060 Uiso 1 1 calc R U . . .
H18C H 1.4211 0.8365 0.9489 0.060 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection
                                'CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)'
_computing_cell_refinement
                                               'CrystalClear-SM Expert 2.0 r13'
_computing_data_reduction
                                               'CrystalClear-SM Expert 2.0 r13'
_computing_structure_solution
                                                'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement                   'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material
                                          'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics                     'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C8 1.7301(16) . ?
S1 C5 1.7427(16) . ?
O1 C1 1.2340(19) . ?
O2 C1 1.3116(19) . ?
O2 H2 0.8400 . ?
N1 C3 1.142(2) . ?
N2 C12 1.373(2) . ?
N2 C15 1.461(2) . ?
N2 C17 1.471(2) . ?
C1 C2 1.466(2) . ?
C2 C4 1.363(2) . ?
C2 C3 1.431(2) . ?
C4 C5 1.414(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(2) . ?
C6 C7 1.392(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.385(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.461(2) . ?
C9 C14 1.400(2) . ?
C9 C10 1.401(2) . ?
C10 C11 1.374(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.407(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.410(2) . ?
C13 C14 1.380(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.516(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.511(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C8 S1 C5 92.14(8) . . ?
C1 O2 H2 109.5 . . ?
C12 N2 C15 122.25(15) . . ?
C12 N2 C17 121.23(15) . . ?
C15 N2 C17 116.43(15) . . ?
O1 C1 O2 123.60(15) . . ?
O1 C1 C2 121.38(14) . . ?
O2 C1 C2 114.99(14) . . ?
C4 C2 C3 124.62(15) . . ?
C4 C2 C1 121.21(14) . . ?
C3 C2 C1 114.14(14) . . ?
N1 C3 C2 177.47(18) . . ?
C2 C4 C5 131.03(15) . . ?
C2 C4 H4 114.5 . . ?
C5 C4 H4 114.5 . . ?
C6 C5 C4 123.20(15) . . ?
C6 C5 S1 110.00(12) . . ?
C4 C5 S1 126.80(12) . . ?
C5 C6 C7 113.93(15) . . ?
C5 C6 H6 123.0 . . ?
C7 C6 H6 123.0 . . ?
C8 C7 C6 113.32(15) . . ?
C8 C7 H7 123.3 . . ?
C6 C7 H7 123.3 . . ?
C7 C8 C9 127.46(15) . . ?
C7 C8 S1 110.60(12) . . ?
C9 C8 S1 121.88(12) . . ?
C14 C9 C10 116.70(15) . . ?
C14 C9 C8 120.15(15) . . ?
C10 C9 C8 123.09(15) . . ?
C11 C10 C9 121.91(16) . . ?
C11 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C10 C11 C12 121.53(16) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
N2 C12 C11 122.57(16) . . ?
N2 C12 C13 120.72(16) . . ?
C11 C12 C13 116.70(15) . . ?
C14 C13 C12 121.20(16) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C9 121.94(16) . . ?
C13 C14 H14 119.0 . . ?
C9 C14 H14 119.0 . . ?
N2 C15 C16 113.83(16) . . ?
N2 C15 H15A 108.8 . . ?
C16 C15 H15A 108.8 . . ?
N2 C15 H15B 108.8 . . ?
C16 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17 C18 113.41(17) . . ?
N2 C17 H17A 108.9 . . ?
C18 C17 H17A 108.9 . . ?
N2 C17 H17B 108.9 . . ?
C18 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
O1 C1 C2 C4 -179.23(16) . . . . ?
O2 C1 C2 C4 -0.7(2) . . . . ?
O1 C1 C2 C3 2.9(2) . . . . ?
O2 C1 C2 C3 -178.56(14) . . . . ?
C3 C2 C4 C5 -7.2(3) . . . . ?
C1 C2 C4 C5 175.18(16) . . . . ?
C2 C4 C5 C6 174.82(18) . . . . ?
C2 C4 C5 S1 -6.6(3) . . . . ?
C8 S1 C5 C6 -0.18(14) . . . . ?
C8 S1 C5 C4 -178.90(16) . . . . ?
C4 C5 C6 C7 179.30(16) . . . . ?
S1 C5 C6 C7 0.5(2) . . . . ?
C5 C6 C7 C8 -0.7(2) . . . . ?
C6 C7 C8 C9 177.75(16) . . . . ?
C6 C7 C8 S1 0.5(2) . . . . ?
C5 S1 C8 C7 -0.21(14) . . . . ?
C5 S1 C8 C9 -177.59(14) . . . . ?
C7 C8 C9 C14 4.1(3) . . . . ?
S1 C8 C9 C14 -178.95(13) . . . . ?
C7 C8 C9 C10 -172.87(17) . . . . ?
S1 C8 C9 C10 4.0(2) . . . . ?
C14 C9 C10 C11 -1.1(3) . . . . ?
C8 C9 C10 C11 176.00(16) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
C15 N2 C12 C11 -11.3(3) . . . . ?
C17 N2 C12 C11 165.13(17) . . . . ?
C15 N2 C12 C13 169.47(17) . . . . ?
C17 N2 C12 C13 -14.1(3) . . . . ?
C10 C11 C12 N2 -177.92(17) . . . . ?
C10 C11 C12 C13 1.3(3) . . . . ?
N2 C12 C13 C14 178.17(16) . . . . ?
C11 C12 C13 C14 -1.1(3) . . . . ?
C12 C13 C14 C9 -0.2(3) . . . . ?
C10 C9 C14 C13 1.3(3) . . . . ?
C8 C9 C14 C13 -175.86(16) . . . . ?
C12 N2 C15 C16 94.5(2) . . . . ?
C17 N2 C15 C16 -82.1(2) . . . . ?
C12 N2 C17 C18 92.9(2) . . . . ?
C15 N2 C17 C18 -90.5(2) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

_shelxl_version_number 2013-3





#==============================================================================
#     End of CIF
#==============================================================================
