# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1061785'
_audit_update_record             
;
2015-04-27 deposited with the CCDC.
2015-07-09 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C28 H34 N2 O2'
_chemical_formula_moiety         'C28 H34 N2 O2'
_chemical_formula_weight         430.59
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   14.8546(3)
_cell_length_b                   4.93706(9)
_cell_length_c                   16.1007(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 92.2269(13)
_cell_angle_gamma                90.0000
_cell_volume                     1179.91(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10937
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      68.19
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       unknown
_exptl_crystal_colour            unknown
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464.00
_exptl_absorpt_coefficient_mu    0.593
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            12796
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_theta_max         68.19
_diffrn_reflns_theta_full        68.19
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_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             2150
_reflns_number_gt                1771
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.1018
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2150
_refine_ls_number_parameters     145
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0497P)²+0.2176P] 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          0.000
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.130
_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 0.0181 0.0091
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(1992, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.54979(7) 0.0542(2) 0.66288(5) 0.0423(3) Uani 1.0 4 d . . .
N1 N 0.63529(7) -0.2804(2) 0.61016(6) 0.0298(3) Uani 1.0 4 d . . .
C1 C 0.58589(8) -0.4146(3) 0.39403(7) 0.0293(3) Uani 1.0 4 d . . .
C2 C 0.64645(9) -0.6217(3) 0.37744(8) 0.0344(4) Uani 1.0 4 d . . .
C3 C 0.70675(9) -0.7168(3) 0.43815(8) 0.0365(4) Uani 1.0 4 d . . .
C4 C 0.70725(8) -0.6108(3) 0.51809(8) 0.0337(3) Uani 1.0 4 d . . .
C5 C 0.64661(8) -0.4070(3) 0.53402(7) 0.0273(3) Uani 1.0 4 d . . .
C6 C 0.58529(7) -0.3002(3) 0.47339(7) 0.0254(3) Uani 1.0 4 d . . .
C7 C 0.53317(8) -0.0857(3) 0.51439(7) 0.0249(3) Uani 1.0 4 d . . .
C8 C 0.56987(8) -0.0850(3) 0.60400(7) 0.0286(3) Uani 1.0 4 d . . .
C9 C 0.68024(8) -0.3561(3) 0.68861(8) 0.0318(3) Uani 1.0 4 d . . .
C10 C 0.77158(8) -0.2218(3) 0.70369(8) 0.0334(3) Uani 1.0 4 d . . .
C11 C 0.81723(8) -0.3234(3) 0.78405(8) 0.0339(4) Uani 1.0 4 d . . .
C12 C 0.90881(9) -0.1977(3) 0.80530(8) 0.0372(4) Uani 1.0 4 d . . .
C13 C 0.95154(9) -0.3059(4) 0.88563(9) 0.0446(4) Uani 1.0 4 d . . .
C14 C 1.04516(10) -0.1907(4) 0.90577(10) 0.0546(5) Uani 1.0 4 d . . .
H1 H 0.5460 -0.3527 0.3523 0.0351 Uiso 1.0 4 calc R . .
H2 H 0.6462 -0.6973 0.3245 0.0413 Uiso 1.0 4 calc R . .
H3 H 0.7473 -0.8527 0.4254 0.0437 Uiso 1.0 4 calc R . .
H4 H 0.7471 -0.6750 0.5595 0.0404 Uiso 1.0 4 calc R . .
H5B H 0.6882 -0.5511 0.6897 0.0381 Uiso 1.0 4 calc R . .
H6A H 0.6418 -0.3081 0.7336 0.0381 Uiso 1.0 4 calc R . .
H7B H 0.7638 -0.0271 0.7068 0.0400 Uiso 1.0 4 calc R . .
H8A H 0.8096 -0.2608 0.6575 0.0400 Uiso 1.0 4 calc R . .
H9B H 0.8245 -0.5182 0.7801 0.0406 Uiso 1.0 4 calc R . .
H10A H 0.7778 -0.2878 0.8294 0.0406 Uiso 1.0 4 calc R . .
H11B H 0.9487 -0.2331 0.7603 0.0446 Uiso 1.0 4 calc R . .
H12A H 0.9019 -0.0029 0.8099 0.0446 Uiso 1.0 4 calc R . .
H13B H 0.9558 -0.5016 0.8818 0.0535 Uiso 1.0 4 calc R . .
H14A H 0.9127 -0.2635 0.9309 0.0535 Uiso 1.0 4 calc R . .
H15A H 1.0416 0.0030 0.9095 0.0656 Uiso 1.0 4 calc R . .
H16C H 1.0849 -0.2397 0.8626 0.0656 Uiso 1.0 4 calc R . .
H17B H 1.0679 -0.2630 0.9578 0.0656 Uiso 1.0 4 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

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

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
O1 C8 1.2175(15) yes . .
N1 C5 1.3921(16) yes . .
N1 C8 1.3701(16) yes . .
N1 C9 1.4544(16) yes . .
C1 C2 1.3947(18) yes . .
C1 C6 1.3974(16) yes . .
C2 C3 1.3820(19) yes . .
C3 C4 1.3891(19) yes . .
C4 C5 1.3811(18) yes . .
C5 C6 1.4113(16) yes . .
C6 C7 1.4821(17) yes . .
C7 C7 1.3659(17) yes . 3_656
C7 C8 1.5224(16) yes . .
C9 C10 1.5211(17) yes . .
C10 C11 1.5222(18) yes . .
C11 C12 1.5221(18) yes . .
C12 C13 1.516(2) yes . .
C13 C14 1.526(2) yes . .
C1 H1 0.930 no . .
C2 H2 0.930 no . .
C3 H3 0.930 no . .
C4 H4 0.930 no . .
C9 H5B 0.970 no . .
C9 H6A 0.970 no . .
C10 H7B 0.970 no . .
C10 H8A 0.970 no . .
C11 H9B 0.970 no . .
C11 H10A 0.970 no . .
C12 H11B 0.970 no . .
C12 H12A 0.970 no . .
C13 H13B 0.970 no . .
C13 H14A 0.970 no . .
C14 H15A 0.960 no . .
C14 H16C 0.960 no . .
C14 H17B 0.960 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C5 N1 C8 111.22(10) yes . . .
C5 N1 C9 125.61(11) yes . . .
C8 N1 C9 122.97(10) yes . . .
C2 C1 C6 119.91(11) yes . . .
C1 C2 C3 121.24(12) yes . . .
C2 C3 C4 120.49(13) yes . . .
C3 C4 C5 117.80(12) yes . . .
N1 C5 C4 126.35(11) yes . . .
N1 C5 C6 110.15(10) yes . . .
C4 C5 C6 123.50(11) yes . . .
C1 C6 C5 117.03(11) yes . . .
C1 C6 C7 135.90(11) yes . . .
C5 C6 C7 107.06(10) yes . . .
C6 C7 C7 132.36(11) yes . . 3_656
C6 C7 C8 104.45(10) yes . . .
C7 C7 C8 123.18(11) yes 3_656 . .
O1 C8 N1 122.39(11) yes . . .
O1 C8 C7 130.51(11) yes . . .
N1 C8 C7 107.10(10) yes . . .
N1 C9 C10 113.78(11) yes . . .
C9 C10 C11 110.93(11) yes . . .
C10 C11 C12 114.93(11) yes . . .
C11 C12 C13 112.89(12) yes . . .
C12 C13 C14 113.44(13) yes . . .
C2 C1 H1 120.043 no . . .
C6 C1 H1 120.048 no . . .
C1 C2 H2 119.381 no . . .
C3 C2 H2 119.376 no . . .
C2 C3 H3 119.756 no . . .
C4 C3 H3 119.751 no . . .
C3 C4 H4 121.100 no . . .
C5 C4 H4 121.099 no . . .
N1 C9 H5B 108.796 no . . .
N1 C9 H6A 108.805 no . . .
C10 C9 H5B 108.810 no . . .
C10 C9 H6A 108.805 no . . .
H5B C9 H6A 107.676 no . . .
C9 C10 H7B 109.443 no . . .
C9 C10 H8A 109.451 no . . .
C11 C10 H7B 109.457 no . . .
C11 C10 H8A 109.455 no . . .
H7B C10 H8A 108.049 no . . .
C10 C11 H9B 108.544 no . . .
C10 C11 H10A 108.543 no . . .
C12 C11 H9B 108.529 no . . .
C12 C11 H10A 108.532 no . . .
H9B C11 H10A 107.530 no . . .
C11 C12 H11B 109.007 no . . .
C11 C12 H12A 109.010 no . . .
C13 C12 H11B 109.014 no . . .
C13 C12 H12A 109.005 no . . .
H11B C12 H12A 107.791 no . . .
C12 C13 H13B 108.881 no . . .
C12 C13 H14A 108.880 no . . .
C14 C13 H13B 108.885 no . . .
C14 C13 H14A 108.883 no . . .
H13B C13 H14A 107.715 no . . .
C13 C14 H15A 109.474 no . . .
C13 C14 H16C 109.469 no . . .
C13 C14 H17B 109.473 no . . .
H15A C14 H16C 109.470 no . . .
H15A C14 H17B 109.473 no . . .
H16C C14 H17B 109.468 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C5 N1 C8 O1 -178.84(10) no . . . .
C5 N1 C8 C7 0.88(13) no . . . .
C8 N1 C5 C4 179.42(10) no . . . .
C8 N1 C5 C6 -1.50(13) no . . . .
C5 N1 C9 C10 87.22(14) no . . . .
C9 N1 C5 C4 -5.56(19) no . . . .
C9 N1 C5 C6 173.51(10) no . . . .
C8 N1 C9 C10 -98.32(13) no . . . .
C9 N1 C8 O1 5.99(18) no . . . .
C9 N1 C8 C7 -174.29(10) no . . . .
C2 C1 C6 C5 -1.07(16) no . . . .
C2 C1 C6 C7 -179.69(11) no . . . .
C6 C1 C2 C3 -0.26(18) no . . . .
C1 C2 C3 C4 1.2(2) no . . . .
C2 C3 C4 C5 -0.76(19) no . . . .
C3 C4 C5 N1 178.31(11) no . . . .
C3 C4 C5 C6 -0.65(18) no . . . .
N1 C5 C6 C1 -177.55(9) no . . . .
N1 C5 C6 C7 1.44(13) no . . . .
C4 C5 C6 C1 1.56(17) no . . . .
C4 C5 C6 C7 -179.45(11) no . . . .
C1 C6 C7 C7 -2.5(3) no . . . 3_656
C1 C6 C7 C8 177.85(12) no . . . .
C5 C6 C7 C7 178.77(11) no . . . 3_656
C5 C6 C7 C8 -0.87(12) no . . . .
C6 C7 C7 C6 180(125743) no . . 3_656 3_656
C6 C7 C7 C8 0.4(2) no . . 3_656 3_656
C6 C7 C8 O1 179.70(12) no . . . .
C6 C7 C8 N1 0.01(12) no . . . .
C7 C7 C8 O1 0.0(2) no 3_656 . . .
C7 C7 C8 N1 -179.67(10) no 3_656 . . .
C8 C7 C7 C6 -0.4(2) no . . 3_656 3_656
C8 C7 C7 C8 180(94633) no . . 3_656 3_656
N1 C9 C10 C11 -176.45(9) no . . . .
C9 C10 C11 C12 -179.20(9) no . . . .
C10 C11 C12 C13 -179.83(10) no . . . .
C11 C12 C13 C14 177.50(10) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O1 C1 2.8148(16) no . 3_656
O1 C5 3.4338(15) no . .
O1 C6 3.5739(15) no . .
O1 C6 3.1579(15) no . 3_656
O1 C7 3.0685(14) no . 3_656
O1 C9 2.8228(16) no . .
N1 C1 3.5900(15) no . .
C1 C4 2.8104(17) no . .
C1 C7 3.4065(17) no . 3_656
C1 C8 3.3829(17) no . 3_656
C2 C5 2.7347(18) no . .
C3 C6 2.8084(18) no . .
C4 C9 3.0603(19) no . .
C5 C10 3.3691(17) no . .
C6 C8 3.2028(16) no . 3_656
C8 C10 3.4113(17) no . .
O1 C9 3.5127(16) no . 1_565
C1 C7 3.4048(17) no . 3_646
C1 C8 3.3858(17) no . 3_646
C2 C7 3.5498(18) no . 3_646
C2 C8 3.5477(18) no . 3_646
C3 C6 3.4572(18) no . 1_545
C3 C7 3.4232(18) no . 1_545
C4 C7 3.4892(18) no . 1_545
C4 C8 3.4320(18) no . 1_545
C6 C3 3.4572(18) no . 1_565
C6 C6 3.3492(16) no . 3_646
C6 C7 3.5152(16) no . 3_646
C7 C1 3.4048(17) no . 3_646
C7 C2 3.5498(18) no . 3_646
C7 C3 3.4232(18) no . 1_565
C7 C4 3.4892(18) no . 1_565
C7 C6 3.5152(16) no . 3_646
C8 C1 3.3858(17) no . 3_646
C8 C2 3.5477(18) no . 3_646
C8 C4 3.4320(18) no . 1_565
C9 O1 3.5127(16) no . 1_545
O1 H1 2.0560 no . 3_656
O1 H6A 2.4988 no . .
O1 H7B 3.2546 no . .
N1 H4 2.7062 no . .
N1 H7B 2.7198 no . .
N1 H8A 2.6718 no . .
C1 H3 3.2540 no . .
C2 H4 3.2492 no . .
C3 H1 3.2540 no . .
C4 H2 3.2398 no . .
C4 H5B 2.8040 no . .
C4 H8A 3.1732 no . .
C5 H1 3.2442 no . .
C5 H3 3.2157 no . .
C5 H5B 2.6552 no . .
C5 H6A 3.2545 no . .
C5 H8A 3.1559 no . .
C6 H2 3.2524 no . .
C6 H4 3.2962 no . .
C7 H1 2.9362 no . .
C7 H1 3.2964 no . 3_656
C8 H1 2.8668 no . 3_656
C8 H5B 3.1780 no . .
C8 H6A 2.5568 no . .
C8 H7B 3.2784 no . .
C9 H4 2.8188 no . .
C9 H9B 2.6756 no . .
C9 H10A 2.6639 no . .
C10 H4 3.2342 no . .
C10 H11B 2.7519 no . .
C10 H12A 2.7544 no . .
C11 H5B 2.6494 no . .
C11 H6A 2.7009 no . .
C11 H13B 2.6902 no . .
C11 H14A 2.7256 no . .
C12 H7B 2.7569 no . .
C12 H8A 2.7677 no . .
C12 H15A 2.7264 no . .
C12 H16C 2.7476 no . .
C12 H17B 3.3565 no . .
C13 H9B 2.7009 no . .
C13 H10A 2.7035 no . .
C14 H11B 2.7056 no . .
C14 H12A 2.7407 no . .
H1 H2 2.3166 no . .
H2 H3 2.2998 no . .
H3 H4 2.3310 no . .
H4 H5B 2.3824 no . .
H4 H8A 2.7235 no . .
H5B H7B 2.8296 no . .
H5B H8A 2.3761 no . .
H5B H9B 2.4531 no . .
H5B H10A 2.8788 no . .
H6A H7B 2.3368 no . .
H6A H8A 2.8299 no . .
H6A H9B 2.9747 no . .
H6A H10A 2.4956 no . .
H7B H9B 2.8290 no . .
H7B H10A 2.3596 no . .
H7B H11B 3.0234 no . .
H7B H12A 2.5922 no . .
H8A H9B 2.3506 no . .
H8A H10A 2.8289 no . .
H8A H11B 2.6012 no . .
H8A H12A 3.0439 no . .
H9B H11B 2.3521 no . .
H9B H12A 2.8250 no . .
H9B H13B 2.4987 no . .
H9B H14A 2.9907 no . .
H10A H11B 2.8250 no . .
H10A H12A 2.3502 no . .
H10A H13B 2.9404 no . .
H10A H14A 2.5393 no . .
H11B H13B 2.3625 no . .
H11B H14A 2.8230 no . .
H11B H15A 2.9629 no . .
H11B H16C 2.5587 no . .
H11B H17B 3.5819 no . .
H12A H13B 2.8229 no . .
H12A H14A 2.3346 no . .
H12A H15A 2.5728 no . .
H12A H16C 3.0485 no . .
H12A H17B 3.5967 no . .
H13B H15A 2.8261 no . .
H13B H16C 2.3435 no . .
H13B H17B 2.3448 no . .
H14A H15A 2.3600 no . .
H14A H16C 2.8257 no . .
H14A H17B 2.3286 no . .
O1 H1 3.2111 no . 4_545
O1 H2 3.4165 no . 3_646
O1 H2 3.0060 no . 4_545
O1 H5B 2.8532 no . 1_565
O1 H6A 3.5990 no . 1_565
O1 H6A 3.4207 no . 2_656
N1 H1 3.3199 no . 3_646
N1 H4 3.5304 no . 1_565
C1 H6A 2.9552 no . 4_544
C1 H10A 3.2304 no . 4_544
C2 H5B 3.5038 no . 4_534
C2 H6A 3.1396 no . 4_544
C2 H7B 3.3914 no . 4_544
C2 H9B 3.5968 no . 4_534
C2 H10A 2.9340 no . 4_544
C3 H9B 3.4052 no . 4_534
C3 H10A 3.2100 no . 4_534
C3 H10A 3.2446 no . 4_544
C4 H17B 3.4313 no . 2_746
C6 H3 3.3785 no . 1_565
C8 H1 3.3549 no . 3_646
C8 H4 3.4190 no . 1_565
C8 H5B 3.4282 no . 1_565
C9 H1 3.5211 no . 4_545
C9 H2 3.1609 no . 4_535
C9 H2 3.5490 no . 4_545
C9 H7B 3.5456 no . 1_545
C10 H2 3.4373 no . 4_545
C10 H4 3.5701 no . 1_565
C10 H5B 3.5396 no . 1_565
C10 H16C 3.5212 no . 2_746
C10 H16C 3.3953 no . 2_756
C11 H2 3.5501 no . 4_535
C11 H3 2.9998 no . 4_535
C11 H16C 3.4902 no . 2_746
C12 H9B 3.5982 no . 1_565
C12 H11B 3.5714 no . 2_746
C12 H11B 3.3207 no . 2_756
C12 H16C 3.5285 no . 2_756
C13 H3 3.5505 no . 4_535
C13 H11B 3.5260 no . 2_746
C13 H17B 3.3200 no . 3_747
C14 H4 3.1156 no . 2_756
C14 H8A 3.2204 no . 2_756
C14 H11B 3.5044 no . 2_756
C14 H14A 3.4939 no . 3_757
C14 H15A 3.4150 no . 3_757
C14 H17B 3.5978 no . 3_757
H1 O1 3.2111 no . 4_544
H1 N1 3.3199 no . 3_646
H1 C8 3.3549 no . 3_646
H1 C9 3.5211 no . 4_544
H1 H2 3.5973 no . 1_565
H1 H5B 3.5494 no . 3_646
H1 H6A 3.4921 no . 3_646
H1 H6A 2.5531 no . 4_544
H1 H10A 3.5459 no . 4_544
H2 O1 3.4165 no . 3_646
H2 O1 3.0060 no . 4_544
H2 C9 3.1609 no . 4_534
H2 C9 3.5490 no . 4_544
H2 C10 3.4373 no . 4_544
H2 C11 3.5501 no . 4_534
H2 H1 3.5973 no . 1_545
H2 H5B 2.5978 no . 4_534
H2 H6A 2.8460 no . 4_534
H2 H6A 2.8924 no . 4_544
H2 H7B 2.8510 no . 4_544
H2 H9B 3.1057 no . 4_534
H2 H10A 3.2051 no . 4_534
H2 H10A 3.0899 no . 4_544
H3 C6 3.3785 no . 1_545
H3 C11 2.9998 no . 4_534
H3 C13 3.5505 no . 4_534
H3 H9B 2.7209 no . 4_534
H3 H10A 2.4078 no . 4_534
H3 H10A 3.5562 no . 4_544
H3 H12A 3.4851 no . 4_544
H3 H13B 3.2817 no . 4_534
H3 H14A 3.1012 no . 4_534
H3 H17B 3.2969 no . 2_746
H4 N1 3.5304 no . 1_545
H4 C8 3.4190 no . 1_545
H4 C10 3.5701 no . 1_545
H4 C14 3.1156 no . 2_746
H4 H7B 2.9427 no . 1_545
H4 H8A 3.4063 no . 1_545
H4 H15A 3.2785 no . 2_746
H4 H16C 2.7675 no . 2_746
H4 H17B 2.8074 no . 2_746
H5B O1 2.8532 no . 1_545
H5B C2 3.5038 no . 4_535
H5B C8 3.4282 no . 1_545
H5B C10 3.5396 no . 1_545
H5B H1 3.5494 no . 3_646
H5B H2 2.5978 no . 4_535
H5B H7B 2.6143 no . 1_545
H6A O1 3.5990 no . 1_545
H6A O1 3.4207 no . 2_646
H6A C1 2.9552 no . 4_545
H6A C2 3.1396 no . 4_545
H6A H1 3.4921 no . 3_646
H6A H1 2.5531 no . 4_545
H6A H2 2.8460 no . 4_535
H6A H2 2.8924 no . 4_545
H7B C2 3.3914 no . 4_545
H7B C9 3.5456 no . 1_565
H7B H2 2.8510 no . 4_545
H7B H4 2.9427 no . 1_565
H7B H5B 2.6143 no . 1_565
H7B H9B 2.9048 no . 1_565
H7B H16C 2.9168 no . 2_756
H8A C14 3.2204 no . 2_746
H8A H4 3.4063 no . 1_565
H8A H15A 2.7561 no . 2_746
H8A H16C 2.8622 no . 2_746
H8A H16C 3.0367 no . 2_756
H9B C2 3.5968 no . 4_535
H9B C3 3.4052 no . 4_535
H9B C12 3.5982 no . 1_545
H9B H2 3.1057 no . 4_535
H9B H3 2.7209 no . 4_535
H9B H7B 2.9048 no . 1_545
H9B H12A 2.6904 no . 1_545
H9B H16C 2.9201 no . 2_746
H10A C1 3.2304 no . 4_545
H10A C2 2.9340 no . 4_545
H10A C3 3.2100 no . 4_535
H10A C3 3.2446 no . 4_545
H10A H1 3.5459 no . 4_545
H10A H2 3.2051 no . 4_535
H10A H2 3.0899 no . 4_545
H10A H3 2.4078 no . 4_535
H10A H3 3.5562 no . 4_545
H11B C12 3.3207 no . 2_746
H11B C12 3.5714 no . 2_756
H11B C13 3.5260 no . 2_756
H11B C14 3.5044 no . 2_746
H11B H11B 2.9261 no . 2_746
H11B H11B 2.9261 no . 2_756
H11B H12A 2.8580 no . 2_746
H11B H13B 2.9678 no . 2_756
H11B H15A 3.0372 no . 2_746
H11B H16C 3.2164 no . 2_746
H11B H16C 3.1660 no . 2_756
H12A H3 3.4851 no . 4_545
H12A H9B 2.6904 no . 1_565
H12A H11B 2.8580 no . 2_756
H12A H13B 2.8345 no . 1_565
H12A H16C 3.0803 no . 2_756
H13B H3 3.2817 no . 4_535
H13B H11B 2.9678 no . 2_746
H13B H12A 2.8345 no . 1_545
H13B H15A 2.7861 no . 1_545
H13B H17B 2.8652 no . 3_747
H14A C14 3.4939 no . 3_757
H14A H3 3.1012 no . 4_535
H14A H15A 2.9289 no . 3_757
H14A H17B 2.9525 no . 3_747
H14A H17B 3.1636 no . 3_757
H15A C14 3.4150 no . 3_757
H15A H4 3.2785 no . 2_756
H15A H8A 2.7561 no . 2_756
H15A H11B 3.0372 no . 2_756
H15A H13B 2.7861 no . 1_565
H15A H14A 2.9289 no . 3_757
H15A H15A 3.2090 no . 3_757
H15A H17B 3.0204 no . 3_757
H16C C10 3.3953 no . 2_746
H16C C10 3.5212 no . 2_756
H16C C11 3.4902 no . 2_756
H16C C12 3.5285 no . 2_746
H16C H4 2.7675 no . 2_756
H16C H7B 2.9168 no . 2_746
H16C H8A 3.0367 no . 2_746
H16C H8A 2.8622 no . 2_756
H16C H9B 2.9201 no . 2_756
H16C H11B 3.1660 no . 2_746
H16C H11B 3.2164 no . 2_756
H16C H12A 3.0803 no . 2_746
H17B C4 3.4313 no . 2_756
H17B C13 3.3200 no . 3_747
H17B C14 3.5978 no . 3_757
H17B H3 3.2969 no . 2_756
H17B H4 2.8074 no . 2_756
H17B H13B 2.8652 no . 3_747
H17B H14A 2.9525 no . 3_747
H17B H14A 3.1636 no . 3_757
H17B H15A 3.0204 no . 3_757
H17B H17B 3.4059 no . 3_747
H17B H17B 3.5864 no . 3_757
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1061786'
_audit_update_record             
;
2015-04-27 deposited with the CCDC.
2015-07-09 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C24 H30 N2 O2 S2'
_chemical_formula_moiety         'C24 H30 N2 O2 S2'
_chemical_formula_weight         442.63
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   19.2970(3)
_cell_length_b                   8.24241(10)
_cell_length_c                   15.6572(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 114.8240
_cell_angle_gamma                90.0000
_cell_volume                     2260.24(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    23254
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      68.22
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       unknown
_exptl_crystal_colour            unknown
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944.00
_exptl_absorpt_coefficient_mu    2.313
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            25324
_diffrn_reflns_av_R_equivalents  0.0782
_diffrn_reflns_theta_max         68.22
_diffrn_reflns_theta_full        68.22
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_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             4124
_reflns_number_gt                3862
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1094
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4124
_refine_ls_number_parameters     271
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0648P)²+0.4334P] 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         0.400
_refine_diff_density_min         -0.210
_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 0.0181 0.0091
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(1992, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.813820(19) 0.00272(4) 0.92059(3) 0.02912(13) Uani 1.0 4 d . . .
S2 S 0.665425(19) 0.18922(4) 0.58789(2) 0.02681(13) Uani 1.0 4 d . . .
O1 O 1.07387(6) -0.06654(13) 0.89444(7) 0.0322(3) Uani 1.0 4 d . . .
O2 O 0.42507(5) -0.07389(12) 0.32003(7) 0.0291(3) Uani 1.0 4 d . . .
N4 N 0.94461(7) -0.08843(15) 0.79849(8) 0.0274(3) Uani 1.0 4 d . . .
N48 N 0.53555(7) 0.05883(15) 0.33601(8) 0.0263(3) Uani 1.0 4 d . . .
C1 C 0.75863(8) -0.0445(2) 0.80504(11) 0.0342(4) Uani 1.0 4 d . . .
C2 C 0.79940(8) -0.07907(18) 0.75387(11) 0.0317(4) Uani 1.0 4 d . . .
C3 C 0.87783(8) -0.06593(16) 0.81185(10) 0.0256(3) Uani 1.0 4 d . . .
C4 C 0.89557(8) -0.02229(16) 0.90364(10) 0.0237(3) Uani 1.0 4 d . . .
C5 C 0.97667(8) -0.01647(15) 0.95406(10) 0.0218(3) Uani 1.0 4 d . . .
C6 C 1.00703(8) -0.05902(16) 0.88205(10) 0.0247(3) Uani 1.0 4 d . . .
C7 C 0.94691(9) -0.14048(18) 0.71060(10) 0.0308(4) Uani 1.0 4 d . . .
C8 C 0.91720(10) -0.01261(17) 0.63358(11) 0.0320(4) Uani 1.0 4 d . . .
C9 C 0.90949(9) -0.07765(18) 0.53918(10) 0.0317(4) Uani 1.0 4 d . . .
C10 C 0.87952(9) 0.04734(19) 0.46032(11) 0.0330(4) Uani 1.0 4 d . . .
C11 C 0.86833(11) -0.0187(2) 0.36494(12) 0.0375(4) Uani 1.0 4 d . . .
C12 C 0.83854(12) 0.1057(3) 0.28632(12) 0.0498(5) Uani 1.0 4 d . . .
C13 C 0.70722(8) 0.24549(18) 0.51499(11) 0.0310(4) Uani 1.0 4 d . . .
C14 C 0.66513(8) 0.20652(18) 0.42185(11) 0.0297(4) Uani 1.0 4 d . . .
C15 C 0.59738(8) 0.12849(17) 0.41175(10) 0.0252(3) Uani 1.0 4 d . . .
C16 C 0.58818(8) 0.11002(16) 0.49418(10) 0.0231(3) Uani 1.0 4 d . . .
C17 C 0.51806(8) 0.02568(16) 0.47303(10) 0.0219(3) Uani 1.0 4 d . . .
C18 C 0.48535(8) -0.00521(16) 0.36859(10) 0.0234(3) Uani 1.0 4 d . . .
C19 C 0.52664(8) 0.04856(19) 0.23879(10) 0.0284(4) Uani 1.0 4 d . . .
C20 C 0.58360(8) -0.06542(18) 0.22604(10) 0.0273(4) Uani 1.0 4 d . . .
C21 C 0.57104(8) -0.07218(17) 0.12311(10) 0.0261(3) Uani 1.0 4 d . . .
C22 C 0.63406(8) -0.16169(18) 0.10819(10) 0.0273(3) Uani 1.0 4 d . . .
C23 C 0.62431(9) -0.15825(18) 0.00612(10) 0.0300(4) Uani 1.0 4 d . . .
C24 C 0.69019(10) -0.2402(3) -0.00679(12) 0.0394(4) Uani 1.0 4 d . . .
H1 H 0.7056 -0.0464 0.7794 0.0410 Uiso 1.0 4 calc R . .
H2 H 0.7784 -0.1070 0.6905 0.0380 Uiso 1.0 4 calc R . .
H3A H 0.9166 -0.2382 0.6887 0.0370 Uiso 1.0 4 calc R . .
H4B H 0.9992 -0.1670 0.7226 0.0370 Uiso 1.0 4 calc R . .
H5B H 0.8678 0.0253 0.6276 0.0384 Uiso 1.0 4 calc R . .
H6A H 0.9518 0.0792 0.6513 0.0384 Uiso 1.0 4 calc R . .
H7A H 0.8752 -0.1700 0.5220 0.0380 Uiso 1.0 4 calc R . .
H8B H 0.9590 -0.1155 0.5456 0.0380 Uiso 1.0 4 calc R . .
H9A H 0.8311 0.0888 0.4560 0.0396 Uiso 1.0 4 calc R . .
H10B H 0.9150 0.1375 0.4763 0.0396 Uiso 1.0 4 calc R . .
H11B H 0.8328 -0.1088 0.3489 0.0450 Uiso 1.0 4 calc R . .
H12A H 0.9167 -0.0602 0.3693 0.0450 Uiso 1.0 4 calc R . .
H13B H 0.7901 0.1460 0.2804 0.0598 Uiso 1.0 4 calc R . .
H14C H 0.8326 0.0559 0.2282 0.0598 Uiso 1.0 4 calc R . .
H15A H 0.8741 0.1940 0.3005 0.0598 Uiso 1.0 4 calc R . .
H16 H 0.7542 0.2978 0.5365 0.0371 Uiso 1.0 4 calc R . .
H17 H 0.6793 0.2284 0.3731 0.0356 Uiso 1.0 4 calc R . .
H18A H 0.5326 0.1561 0.2176 0.0340 Uiso 1.0 4 calc R . .
H19B H 0.4753 0.0117 0.1993 0.0340 Uiso 1.0 4 calc R . .
H20B H 0.5780 -0.1734 0.2470 0.0328 Uiso 1.0 4 calc R . .
H21A H 0.6351 -0.0284 0.2644 0.0328 Uiso 1.0 4 calc R . .
H22B H 0.5227 -0.1254 0.0867 0.0313 Uiso 1.0 4 calc R . .
H23A H 0.5677 0.0377 0.0995 0.0313 Uiso 1.0 4 calc R . .
H24B H 0.6350 -0.2737 0.1277 0.0327 Uiso 1.0 4 calc R . .
H25A H 0.6828 -0.1132 0.1480 0.0327 Uiso 1.0 4 calc R . .
H26B H 0.5770 -0.2124 -0.0333 0.0360 Uiso 1.0 4 calc R . .
H27A H 0.6205 -0.0464 -0.0146 0.0360 Uiso 1.0 4 calc R . .
H28A H 0.7370 -0.1852 0.0307 0.0473 Uiso 1.0 4 calc R . .
H29C H 0.6812 -0.2353 -0.0719 0.0473 Uiso 1.0 4 calc R . .
H30B H 0.6937 -0.3514 0.0127 0.0473 Uiso 1.0 4 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'


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

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
S1 C1 1.7149(15) yes . .
S1 C4 1.7184(18) yes . .
S2 C13 1.715(2) yes . .
S2 C16 1.7217(13) yes . .
O1 C6 1.223(2) yes . .
O2 C18 1.2284(16) yes . .
N4 C3 1.402(3) yes . .
N4 C6 1.3777(16) yes . .
N4 C7 1.460(3) yes . .
N48 C15 1.4041(16) yes . .
N48 C18 1.376(3) yes . .
N48 C19 1.461(2) yes . .
C1 C2 1.368(3) yes . .
C2 C3 1.4046(19) yes . .
C3 C4 1.378(3) yes . .
C4 C5 1.4273(19) yes . .
C5 C5 1.3661(19) yes . 3_757
C5 C6 1.514(3) yes . .
C7 C8 1.521(2) yes . .
C8 C9 1.520(3) yes . .
C9 C10 1.523(2) yes . .
C10 C11 1.517(3) yes . .
C11 C12 1.517(3) yes . .
C13 C14 1.377(2) yes . .
C14 C15 1.405(3) yes . .
C15 C16 1.383(3) yes . .
C16 C17 1.431(2) yes . .
C17 C17 1.368(3) yes . 3_656
C17 C18 1.507(2) yes . .
C19 C20 1.521(3) yes . .
C20 C21 1.527(3) yes . .
C21 C22 1.522(3) yes . .
C22 C23 1.529(3) yes . .
C23 C24 1.526(3) yes . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 S1 C4 90.78(8) yes . . .
C13 S2 C16 90.93(8) yes . . .
C3 N4 C6 109.09(14) yes . . .
C3 N4 C7 124.97(11) yes . . .
C6 N4 C7 125.90(15) yes . . .
C15 N48 C18 108.95(13) yes . . .
C15 N48 C19 126.18(15) yes . . .
C18 N48 C19 124.82(11) yes . . .
S1 C1 C2 114.21(11) yes . . .
C1 C2 C3 109.51(14) yes . . .
N4 C3 C2 134.58(15) yes . . .
N4 C3 C4 110.41(12) yes . . .
C2 C3 C4 115.00(16) yes . . .
S1 C4 C3 110.50(11) yes . . .
S1 C4 C5 140.81(13) yes . . .
C3 C4 C5 108.68(16) yes . . .
C4 C5 C5 132.37(17) yes . . 3_757
C4 C5 C6 104.93(12) yes . . .
C5 C5 C6 122.70(14) yes 3_757 . .
O1 C6 N4 125.82(16) yes . . .
O1 C6 C5 127.29(12) yes . . .
N4 C6 C5 106.89(13) yes . . .
N4 C7 C8 113.16(14) yes . . .
C7 C8 C9 112.15(13) yes . . .
C8 C9 C10 113.49(13) yes . . .
C9 C10 C11 113.83(14) yes . . .
C10 C11 C12 113.90(15) yes . . .
S2 C13 C14 114.13(12) yes . . .
C13 C14 C15 109.47(17) yes . . .
N48 C15 C14 134.65(16) yes . . .
N48 C15 C16 110.28(14) yes . . .
C14 C15 C16 115.04(13) yes . . .
S2 C16 C15 110.43(12) yes . . .
S2 C16 C17 141.04(14) yes . . .
C15 C16 C17 108.48(12) yes . . .
C16 C17 C17 133.21(13) yes . . 3_656
C16 C17 C18 104.94(15) yes . . .
C17 C17 C18 121.85(13) yes 3_656 . .
O2 C18 N48 125.35(15) yes . . .
O2 C18 C17 127.30(16) yes . . .
N48 C18 C17 107.35(12) yes . . .
N48 C19 C20 113.39(11) yes . . .
C19 C20 C21 110.96(11) yes . . .
C20 C21 C22 113.37(11) yes . . .
C21 C22 C23 113.32(12) yes . . .
C22 C23 C24 112.74(12) yes . . .
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 1061787'
_audit_update_record             
;
2015-04-27 deposited with the CCDC.
2015-07-09 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C32 H34 N2 O2 S2'
_chemical_formula_moiety         'C32 H34 N2 O2 S2'
_chemical_formula_weight         542.75
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   5.05526(9)
_cell_length_b                   8.31652(15)
_cell_length_c                   16.4731(3)
_cell_angle_alpha                79.8632(10)
_cell_angle_beta                 87.7600(12)
_cell_angle_gamma                86.0505(10)
_cell_volume                     679.88(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5442
_cell_measurement_theta_min      5.42
_cell_measurement_theta_max      68.17
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       unknown
_exptl_crystal_colour            unknown
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288.00
_exptl_absorpt_coefficient_mu    2.028
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            7927
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_theta_max         68.17
_diffrn_reflns_theta_full        68.16
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_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             2436
_reflns_number_gt                1900
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1455
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2436
_refine_ls_number_parameters     172
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0799P)²+0.0000P] 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         0.410
_refine_diff_density_min         -0.240
_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 0.0181 0.0091
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(1992, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.10362(12) 0.72762(6) 0.96276(3) 0.0288(3) Uani 1.0 2 d . . .
O1 O 0.5246(4) 1.29697(18) 0.91145(9) 0.0326(5) Uani 1.0 2 d . . .
N1 N 0.2148(4) 1.1678(3) 0.85148(12) 0.0279(5) Uani 1.0 2 d . . .
C1 C -0.1019(5) 0.7731(3) 0.87842(14) 0.0281(6) Uani 1.0 2 d . . .
C2 C -0.2823(5) 0.6685(3) 0.85642(15) 0.0302(6) Uani 1.0 2 d . . .
C3 C -0.4278(6) 0.7212(3) 0.78740(16) 0.0362(7) Uani 1.0 2 d . . .
C4 C -0.4022(5) 0.8768(3) 0.73872(15) 0.0366(7) Uani 1.0 2 d . . .
C5 C -0.2304(5) 0.9826(3) 0.76100(15) 0.0331(6) Uani 1.0 2 d . . .
C6 C -0.0779(5) 0.9327(3) 0.83164(14) 0.0266(6) Uani 1.0 2 d . . .
C7 C 0.1108(5) 1.0126(3) 0.86968(14) 0.0264(6) Uani 1.0 2 d . . .
C8 C 0.2263(5) 0.9208(3) 0.93832(14) 0.0262(6) Uani 1.0 2 d . . .
C9 C 0.4162(5) 1.0156(3) 0.96782(13) 0.0247(6) Uani 1.0 2 d . . .
C10 C 0.3995(5) 1.1772(3) 0.90910(14) 0.0250(6) Uani 1.0 2 d . . .
C11 C 0.0987(5) 1.3142(3) 0.79948(14) 0.0292(6) Uani 1.0 2 d . . .
C12 C 0.2278(5) 1.3539(3) 0.71403(14) 0.0324(6) Uani 1.0 2 d . . .
C13 C 0.0957(5) 1.5089(3) 0.66505(14) 0.0344(6) Uani 1.0 2 d . . .
C14 C 0.2430(6) 1.5790(3) 0.58671(15) 0.0381(7) Uani 1.0 2 d . . .
C15 C 0.1209(6) 1.7405(4) 0.54274(16) 0.0469(8) Uani 1.0 2 d . . .
C16 C 0.2678(7) 1.8130(4) 0.46464(17) 0.0649(10) Uani 1.0 2 d . . .
H1 H -0.3027 0.5656 0.8880 0.0363 Uiso 1.0 2 calc R . .
H2 H -0.5471 0.6523 0.7722 0.0434 Uiso 1.0 2 calc R . .
H3 H -0.5011 0.9083 0.6915 0.0439 Uiso 1.0 2 calc R . .
H4 H -0.2157 1.0861 0.7295 0.0397 Uiso 1.0 2 calc R . .
H5A H 0.1110 1.4069 0.8273 0.0351 Uiso 1.0 2 calc R . .
H6B H -0.0881 1.3002 0.7935 0.0351 Uiso 1.0 2 calc R . .
H7A H 0.2129 1.2633 0.6849 0.0389 Uiso 1.0 2 calc R . .
H8B H 0.4148 1.3686 0.7191 0.0389 Uiso 1.0 2 calc R . .
H9B H -0.0805 1.4853 0.6510 0.0413 Uiso 1.0 2 calc R . .
H10A H 0.0752 1.5914 0.7001 0.0413 Uiso 1.0 2 calc R . .
H11A H 0.2498 1.5005 0.5494 0.0457 Uiso 1.0 2 calc R . .
H12B H 0.4240 1.5940 0.5999 0.0457 Uiso 1.0 2 calc R . .
H13B H -0.0595 1.7250 0.5292 0.0563 Uiso 1.0 2 calc R . .
H14A H 0.1123 1.8184 0.5803 0.0563 Uiso 1.0 2 calc R . .
H15B H 0.2744 1.7380 0.4264 0.0779 Uiso 1.0 2 calc R . .
H16C H 0.4450 1.8327 0.4775 0.0779 Uiso 1.0 2 calc R . .
H17A H 0.1773 1.9143 0.4404 0.0779 Uiso 1.0 2 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'


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

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
S1 C1 1.740(3) yes . .
S1 C8 1.737(3) yes . .
O1 C10 1.223(3) yes . .
N1 C7 1.406(3) yes . .
N1 C10 1.373(4) yes . .
N1 C11 1.461(3) yes . .
C1 C2 1.402(4) yes . .
C1 C6 1.423(3) yes . .
C2 C3 1.368(4) yes . .
C3 C4 1.408(4) yes . .
C4 C5 1.381(4) yes . .
C5 C6 1.406(4) yes . .
C6 C7 1.423(4) yes . .
C7 C8 1.374(3) yes . .
C8 C9 1.434(4) yes . .
C9 C9 1.361(3) yes . 2_677
C9 C10 1.510(3) yes . .
C11 C12 1.520(4) yes . .
C12 C13 1.521(3) yes . .
C13 C14 1.510(4) yes . .
C14 C15 1.513(4) yes . .
C15 C16 1.511(4) yes . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 S1 C8 90.25(12) yes . . .
C7 N1 C10 108.52(18) yes . . .
C7 N1 C11 127.2(2) yes . . .
C10 N1 C11 121.65(19) yes . . .
S1 C1 C2 125.41(17) yes . . .
S1 C1 C6 113.92(19) yes . . .
C2 C1 C6 120.7(3) yes . . .
C1 C2 C3 118.5(2) yes . . .
C2 C3 C4 121.9(3) yes . . .
C3 C4 C5 120.1(3) yes . . .
C4 C5 C6 119.5(2) yes . . .
C1 C6 C5 119.2(3) yes . . .
C1 C6 C7 108.4(2) yes . . .
C5 C6 C7 132.4(2) yes . . .
N1 C7 C6 134.0(2) yes . . .
N1 C7 C8 110.6(3) yes . . .
C6 C7 C8 115.4(2) yes . . .
S1 C8 C7 112.04(19) yes . . .
S1 C8 C9 139.19(17) yes . . .
C7 C8 C9 108.77(19) yes . . .
C8 C9 C9 133.08(19) yes . . 2_677
C8 C9 C10 104.32(18) yes . . .
C9 C9 C10 122.6(2) yes 2_677 . .
O1 C10 N1 125.06(19) yes . . .
O1 C10 C9 127.1(2) yes . . .
N1 C10 C9 107.79(19) yes . . .
N1 C11 C12 114.61(19) yes . . .
C11 C12 C13 110.7(2) yes . . .
C12 C13 C14 115.0(2) yes . . .
C13 C14 C15 114.1(3) yes . . .
C14 C15 C16 114.7(3) yes . . .



#==============================================================================

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

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