# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               'RSC Advances'
_journal_coden_cambridge         1500
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Sun, Qi'
_publ_author_name                'Qi Sun'
_publ_contact_author_email       sunqi@bjmu.edu.cn

data_5262
_database_code_depnum_ccdc_archive 'CCDC 866961'
#TrackingRef '- X-ray of compound 1b.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H18 N2 O2 S'
_chemical_formula_sum            'C21 H18 N2 O2 S'
_chemical_formula_weight         362.43

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-p 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.917(5)
_cell_length_b                   19.319(8)
_cell_length_c                   11.750(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.247(13)
_cell_angle_gamma                90.00
_cell_volume                     1796.7(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2995
_cell_measurement_theta_min      4.40
_cell_measurement_theta_max      72.48

_exptl_crystal_description       block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    1.742
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_monochromator  Multilayer
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       \w\k
_diffrn_detector_area_resol_mean 0
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            28800
_diffrn_reflns_av_R_equivalents  0.0751
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.40
_diffrn_reflns_theta_max         72.48
_reflns_number_total             3521
_reflns_number_gt                2995
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPII(Johnson,1976) and PLUTON(Spek,1990)'
_computing_publication_material  'SHELXL97(Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0755P)^2^+0.2753P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3521
_refine_ls_number_parameters     242
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1413
_refine_ls_wR_factor_gt          0.1322
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.51842(7) 0.02385(3) 0.67381(4) 0.0594(2) Uani 1 1 d . . .
O1 O 1.2524(2) -0.02497(8) 0.94725(16) 0.0768(5) Uani 1 1 d . . .
O2 O 1.22121(18) 0.08985(7) 0.94232(11) 0.0553(4) Uani 1 1 d . . .
N1 N 0.8162(3) -0.03518(8) 0.72232(14) 0.0566(4) Uani 1 1 d . . .
N2 N 0.76569(18) 0.08104(7) 0.78024(11) 0.0406(3) Uani 1 1 d . . .
C1 C 0.9667(3) -0.03358(9) 0.78573(16) 0.0532(5) Uani 1 1 d . . .
C2 C 1.0281(3) 0.02511(9) 0.83502(14) 0.0459(4) Uani 1 1 d . . .
C3 C 0.9460(2) 0.09418(8) 0.80793(13) 0.0398(4) Uani 1 1 d . . .
H3A H 0.9528 0.1231 0.8764 0.048 Uiso 1 1 calc R . .
C4 C 0.6354(2) 0.13043(8) 0.77845(13) 0.0405(4) Uani 1 1 d . . .
C5 C 0.4964(3) 0.10715(10) 0.72424(16) 0.0506(4) Uani 1 1 d . . .
H5A H 0.390(3) 0.1291(11) 0.7133(18) 0.061 Uiso 1 1 d . . .
C6 C 0.7233(3) 0.02031(9) 0.72877(15) 0.0480(4) Uani 1 1 d . . .
C7 C 1.0508(4) -0.10317(11) 0.7938(2) 0.0775(7) Uani 1 1 d . . .
H7A H 1.1533 -0.0993 0.8386 0.116 Uiso 1 1 calc R . .
H7B H 1.0767 -0.1192 0.7188 0.116 Uiso 1 1 calc R . .
H7C H 0.9763 -0.1355 0.8292 0.116 Uiso 1 1 calc R . .
C8 C 1.1760(3) 0.02509(10) 0.91181(16) 0.0515(5) Uani 1 1 d . . .
C9 C 1.3667(3) 0.09564(14) 1.01739(19) 0.0662(6) Uani 1 1 d . . .
H9A H 1.3884 0.1436 1.0335 0.099 Uiso 1 1 calc R . .
H9B H 1.4631 0.0757 0.9816 0.099 Uiso 1 1 calc R . .
H9C H 1.3456 0.0715 1.0871 0.099 Uiso 1 1 calc R . .
C10 C 1.0292(2) 0.13282(8) 0.71142(14) 0.0406(4) Uani 1 1 d . . .
C11 C 1.0656(3) 0.09974(10) 0.60989(15) 0.0519(4) Uani 1 1 d . . .
H11A H 1.0358 0.0536 0.5997 0.062 Uiso 1 1 calc R . .
C12 C 1.1454(3) 0.13481(14) 0.52410(16) 0.0657(6) Uani 1 1 d . . .
H12A H 1.1680 0.1123 0.4561 0.079 Uiso 1 1 calc R . .
C13 C 1.1917(3) 0.20270(13) 0.5385(2) 0.0708(6) Uani 1 1 d . . .
H13A H 1.2464 0.2261 0.4808 0.085 Uiso 1 1 calc R . .
C14 C 1.1572(3) 0.23591(12) 0.6382(2) 0.0668(6) Uani 1 1 d . . .
H14A H 1.193(4) 0.2820(15) 0.648(2) 0.080 Uiso 1 1 d . . .
C15 C 1.0761(3) 0.20133(9) 0.72448(18) 0.0530(5) Uani 1 1 d . . .
H15A H 1.0530 0.2244 0.7919 0.064 Uiso 1 1 calc R . .
C16 C 0.6491(2) 0.19862(9) 0.83453(14) 0.0421(4) Uani 1 1 d . . .
C17 C 0.5764(3) 0.25583(10) 0.78019(16) 0.0534(5) Uani 1 1 d . . .
H17A H 0.5281 0.2508 0.7078 0.064 Uiso 1 1 calc R . .
C18 C 0.5751(3) 0.31957(11) 0.8322(2) 0.0689(6) Uani 1 1 d . . .
H18A H 0.5234 0.3570 0.7958 0.083 Uiso 1 1 calc R . .
C19 C 0.6502(4) 0.32801(12) 0.9379(2) 0.0747(7) Uani 1 1 d . . .
H19A H 0.6521 0.3714 0.9722 0.090 Uiso 1 1 calc R . .
C20 C 0.7226(3) 0.27209(13) 0.99294(18) 0.0657(6) Uani 1 1 d . . .
H20A H 0.7736 0.2780 1.0643 0.079 Uiso 1 1 calc R . .
C21 C 0.7202(3) 0.20727(11) 0.94308(15) 0.0511(5) Uani 1 1 d . . .
H21A H 0.7660 0.1695 0.9819 0.061 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0532(4) 0.0560(3) 0.0684(3) -0.0075(2) -0.0117(2) -0.0092(2)
O1 0.0652(12) 0.0679(10) 0.0967(12) 0.0220(8) -0.0143(9) 0.0221(8)
O2 0.0438(8) 0.0644(8) 0.0571(7) 0.0076(6) -0.0107(6) 0.0078(6)
N1 0.0640(12) 0.0413(8) 0.0645(9) -0.0042(7) -0.0016(8) 0.0024(7)
N2 0.0376(9) 0.0397(7) 0.0445(7) -0.0008(5) -0.0022(6) 0.0023(5)
C1 0.0577(14) 0.0457(10) 0.0563(10) 0.0043(7) 0.0048(9) 0.0075(8)
C2 0.0435(11) 0.0457(9) 0.0487(9) 0.0061(7) 0.0043(7) 0.0095(7)
C3 0.0351(10) 0.0426(8) 0.0414(7) 0.0000(6) -0.0045(6) 0.0050(6)
C4 0.0344(10) 0.0471(9) 0.0400(7) 0.0009(6) -0.0009(6) 0.0046(7)
C5 0.0372(11) 0.0584(11) 0.0560(10) -0.0008(8) -0.0064(8) 0.0017(8)
C6 0.0528(12) 0.0421(9) 0.0489(9) -0.0014(7) 0.0000(8) -0.0032(7)
C7 0.088(2) 0.0454(11) 0.0988(17) 0.0022(10) -0.0023(14) 0.0182(11)
C8 0.0443(12) 0.0585(11) 0.0519(9) 0.0136(8) 0.0037(8) 0.0126(8)
C9 0.0435(13) 0.0924(16) 0.0623(11) 0.0109(10) -0.0093(9) 0.0053(11)
C10 0.0305(9) 0.0444(8) 0.0467(8) 0.0037(6) -0.0047(6) 0.0046(6)
C11 0.0509(12) 0.0579(10) 0.0468(9) -0.0023(7) -0.0017(8) -0.0007(8)
C12 0.0574(15) 0.0931(16) 0.0466(10) 0.0056(9) 0.0007(9) 0.0046(11)
C13 0.0594(15) 0.0801(15) 0.0730(13) 0.0326(11) 0.0051(11) 0.0042(11)
C14 0.0525(14) 0.0510(11) 0.0971(16) 0.0205(11) 0.0064(11) 0.0014(9)
C15 0.0442(12) 0.0436(9) 0.0714(11) 0.0012(8) 0.0017(9) 0.0050(8)
C16 0.0344(10) 0.0476(9) 0.0444(8) -0.0029(6) 0.0011(7) 0.0028(7)
C17 0.0511(13) 0.0515(10) 0.0575(10) 0.0004(8) -0.0010(8) 0.0069(8)
C18 0.0723(17) 0.0498(11) 0.0850(14) -0.0027(10) 0.0088(12) 0.0091(10)
C19 0.0784(18) 0.0591(13) 0.0871(15) -0.0255(11) 0.0136(13) -0.0040(11)
C20 0.0560(14) 0.0847(15) 0.0564(11) -0.0250(10) 0.0024(9) -0.0059(11)
C21 0.0404(11) 0.0682(12) 0.0447(8) -0.0076(8) 0.0004(7) 0.0037(8)

_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 C5 1.725(2) . ?
S1 C6 1.734(2) . ?
O1 C8 1.210(2) . ?
O2 C8 1.348(3) . ?
O2 C9 1.440(3) . ?
N1 C6 1.304(2) . ?
N1 C1 1.392(3) . ?
N2 C6 1.359(2) . ?
N2 C4 1.405(2) . ?
N2 C3 1.479(2) . ?
C1 C2 1.358(3) . ?
C1 C7 1.503(3) . ?
C2 C8 1.463(3) . ?
C2 C3 1.515(2) . ?
C3 C10 1.520(2) . ?
C3 H3A 0.9800 . ?
C4 C5 1.337(3) . ?
C4 C16 1.476(2) . ?
C5 H5A 0.95(2) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C15 1.382(3) . ?
C10 C11 1.389(3) . ?
C11 C12 1.379(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.372(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.368(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.383(3) . ?
C14 H14A 0.94(3) . ?
C15 H15A 0.9300 . ?
C16 C21 1.393(2) . ?
C16 C17 1.395(3) . ?
C17 C18 1.375(3) . ?
C17 H17A 0.9300 . ?
C18 C19 1.375(4) . ?
C18 H18A 0.9300 . ?
C19 C20 1.378(4) . ?
C19 H19A 0.9300 . ?
C20 C21 1.382(3) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?

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
C5 S1 C6 90.55(9) . . ?
C8 O2 C9 116.06(16) . . ?
C6 N1 C1 115.36(16) . . ?
C6 N2 C4 113.92(16) . . ?
C6 N2 C3 118.30(14) . . ?
C4 N2 C3 126.25(14) . . ?
C2 C1 N1 122.77(17) . . ?
C2 C1 C7 124.5(2) . . ?
N1 C1 C7 112.76(19) . . ?
C1 C2 C8 122.49(16) . . ?
C1 C2 C3 119.82(18) . . ?
C8 C2 C3 117.66(16) . . ?
N2 C3 C2 107.63(14) . . ?
N2 C3 C10 110.63(13) . . ?
C2 C3 C10 113.46(14) . . ?
N2 C3 H3A 108.3 . . ?
C2 C3 H3A 108.3 . . ?
C10 C3 H3A 108.3 . . ?
C5 C4 N2 112.02(16) . . ?
C5 C4 C16 124.36(16) . . ?
N2 C4 C16 123.56(15) . . ?
C4 C5 S1 112.89(15) . . ?
C4 C5 H5A 129.3(14) . . ?
S1 C5 H5A 117.7(14) . . ?
N1 C6 N2 127.0(2) . . ?
N1 C6 S1 122.38(15) . . ?
N2 C6 S1 110.60(14) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 O2 121.5(2) . . ?
O1 C8 C2 126.9(2) . . ?
O2 C8 C2 111.60(14) . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 118.41(17) . . ?
C15 C10 C3 120.48(15) . . ?
C11 C10 C3 121.07(16) . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11A 119.7 . . ?
C10 C11 H11A 119.7 . . ?
C13 C12 C11 120.3(2) . . ?
C13 C12 H12A 119.8 . . ?
C11 C12 H12A 119.8 . . ?
C14 C13 C12 119.8(2) . . ?
C14 C13 H13A 120.1 . . ?
C12 C13 H13A 120.1 . . ?
C13 C14 C15 120.3(2) . . ?
C13 C14 H14A 118.9(16) . . ?
C15 C14 H14A 120.7(16) . . ?
C10 C15 C14 120.59(19) . . ?
C10 C15 H15A 119.7 . . ?
C14 C15 H15A 119.7 . . ?
C21 C16 C17 118.60(17) . . ?
C21 C16 C4 122.70(16) . . ?
C17 C16 C4 118.51(16) . . ?
C18 C17 C16 120.9(2) . . ?
C18 C17 H17A 119.6 . . ?
C16 C17 H17A 119.6 . . ?
C17 C18 C19 120.0(2) . . ?
C17 C18 H18A 120.0 . . ?
C19 C18 H18A 120.0 . . ?
C18 C19 C20 119.9(2) . . ?
C18 C19 H19A 120.1 . . ?
C20 C19 H19A 120.1 . . ?
C19 C20 C21 120.6(2) . . ?
C19 C20 H20A 119.7 . . ?
C21 C20 H20A 119.7 . . ?
C20 C21 C16 119.89(19) . . ?
C20 C21 H21A 120.1 . . ?
C16 C21 H21A 120.1 . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        72.48
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.044