# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_191113b
_database_code_depnum_ccdc_archive 'CCDC 1966544'
loop_
_audit_author_name
_audit_author_address
'Bruker '
;Liaocheng University
China
;
_audit_update_record             
;
2019-11-19 deposited with the CCDC.	2020-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H14 N2 O S'
_chemical_formula_weight         246.32

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'
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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   6.7032(6)
_cell_length_b                   8.5139(9)
_cell_length_c                   22.447(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1281.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1722
_cell_measurement_theta_min      2.559
_cell_measurement_theta_max      27.93

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9005
_exptl_absorpt_correction_T_max  0.9451
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6334
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_sigmaI/netI    0.0519
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2228
_reflns_number_gt                1266
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0012P)²+0.6813P] where P=(Fo²+2Fc²)/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       0.0022(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.7(3)
_refine_ls_number_reflns         2228
_refine_ls_number_parameters     156
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1043
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1177
_refine_ls_wR_factor_gt          0.0972
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.176
_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
N1 N 0.6541(5) 0.3810(4) 0.20999(15) 0.0742(11) Uani 1 1 d . . .
H1 H 0.6134 0.4766 0.2076 0.089 Uiso 1 1 calc R . .
N2 N 0.4398(5) 0.3605(4) 0.28859(15) 0.0680(10) Uani 1 1 d . . .
H2 H 0.3935 0.4485 0.2758 0.082 Uiso 1 1 calc R . .
O1 O 0.6509(4) 0.1569(3) 0.26472(12) 0.0693(8) Uani 1 1 d . . .
S1 S 1.2691(7) 0.1386(5) 0.14446(14) 0.0916(6) Uani 0.599(3) 1 d PD A 1
S1' S 1.1803(11) 0.3928(7) 0.0705(2) 0.0916(6) Uani 0.401(3) 1 d PD A 2
C1 C 0.5864(7) 0.2910(5) 0.25505(18) 0.0625(11) Uani 1 1 d . . .
C2 C 0.7917(6) 0.3243(5) 0.16552(18) 0.0704(12) Uani 1 1 d . . .
H2A H 0.7542 0.3671 0.1271 0.084 Uiso 1 1 calc R . .
H2B H 0.7810 0.2108 0.1631 0.084 Uiso 1 1 calc R . .
C3 C 1.0034(6) 0.3673(7) 0.1783(2) 0.0959(17) Uani 1 1 d . A .
H3A H 1.0152 0.4808 0.1792 0.115 Uiso 1 1 calc R . .
H3B H 1.0393 0.3280 0.2174 0.115 Uiso 1 1 calc R . .
C4 C 1.1459(6) 0.3034(5) 0.13358(18) 0.0737(13) Uani 1 1 d D . .
C5 C 1.196(2) 0.3574(17) 0.0766(5) 0.0916(6) Uani 0.599(3) 1 d PD A 1
H5 H 1.1418 0.4488 0.0608 0.110 Uiso 0.599(3) 1 calc PR A 1
C5' C 1.256(4) 0.162(2) 0.1301(7) 0.0916(6) Uani 0.401(3) 1 d PD A 2
H5' H 1.2482 0.0866 0.1600 0.110 Uiso 0.401(3) 1 calc PR A 2
C6 C 1.3362(7) 0.2642(7) 0.0442(2) 0.0960(18) Uani 1 1 d D . .
H6 H 1.3876 0.2850 0.0066 0.115 Uiso 1 1 calc R A 1
C7 C 1.3791(7) 0.1394(7) 0.0793(2) 0.0985(17) Uani 1 1 d D A .
H7 H 1.4651 0.0597 0.0673 0.118 Uiso 1 1 calc R B 1
C8 C 0.3585(7) 0.3023(5) 0.34136(18) 0.0624(11) Uani 1 1 d . . .
C9 C 0.4570(7) 0.2003(5) 0.37966(19) 0.0707(13) Uani 1 1 d . . .
H9 H 0.5835 0.1635 0.3699 0.085 Uiso 1 1 calc R . .
C10 C 0.3684(8) 0.1533(6) 0.4319(2) 0.0849(14) Uani 1 1 d . . .
H10 H 0.4348 0.0832 0.4568 0.102 Uiso 1 1 calc R . .
C11 C 0.1840(9) 0.2081(6) 0.4481(2) 0.0907(17) Uani 1 1 d . . .
H11 H 0.1259 0.1760 0.4837 0.109 Uiso 1 1 calc R . .
C12 C 0.0859(8) 0.3111(6) 0.4111(2) 0.0898(16) Uani 1 1 d . . .
H12 H -0.0381 0.3507 0.4221 0.108 Uiso 1 1 calc R . .
C13 C 0.1702(7) 0.3558(5) 0.35804(18) 0.0730(12) Uani 1 1 d . . .
H13 H 0.1005 0.4228 0.3328 0.088 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
N1 0.087(3) 0.051(2) 0.084(2) 0.003(2) 0.025(2) 0.003(2)
N2 0.075(2) 0.052(2) 0.077(2) -0.001(2) 0.0111(19) 0.005(2)
O1 0.081(2) 0.0415(16) 0.085(2) 0.0004(15) 0.0023(16) 0.0039(17)
S1 0.0788(12) 0.0893(16) 0.1066(14) 0.0015(11) -0.0029(12) 0.0053(11)
S1' 0.0788(12) 0.0893(16) 0.1066(14) 0.0015(11) -0.0029(12) 0.0053(11)
C1 0.067(3) 0.053(3) 0.067(3) -0.003(2) 0.000(2) -0.007(2)
C2 0.066(3) 0.067(3) 0.079(3) 0.000(2) 0.007(2) -0.005(2)
C3 0.059(3) 0.128(5) 0.101(4) -0.042(4) 0.004(3) -0.012(3)
C4 0.052(3) 0.083(3) 0.085(3) -0.018(3) -0.004(2) -0.005(2)
C5 0.0788(12) 0.0893(16) 0.1066(14) 0.0015(11) -0.0029(12) 0.0053(11)
C5' 0.0788(12) 0.0893(16) 0.1066(14) 0.0015(11) -0.0029(12) 0.0053(11)
C6 0.067(3) 0.127(5) 0.095(4) -0.025(4) 0.010(3) 0.008(4)
C7 0.070(3) 0.094(4) 0.131(5) -0.041(4) -0.003(3) 0.001(3)
C8 0.079(3) 0.051(3) 0.058(2) -0.006(2) -0.003(2) -0.003(2)
C9 0.079(3) 0.068(3) 0.065(3) 0.003(3) -0.009(2) 0.002(3)
C10 0.110(4) 0.078(4) 0.067(3) -0.001(3) -0.011(3) 0.014(4)
C11 0.118(5) 0.086(4) 0.068(3) 0.006(3) 0.017(3) 0.005(4)
C12 0.090(4) 0.096(4) 0.083(3) 0.000(3) 0.012(3) 0.007(3)
C13 0.077(3) 0.071(3) 0.071(3) 0.000(3) 0.006(3) 0.005(3)

_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
N1 C1 1.348(5) . ?
N1 C2 1.442(5) . ?
N1 H1 0.8600 . ?
N2 C1 1.372(5) . ?
N2 C8 1.395(5) . ?
N2 H2 0.8600 . ?
O1 C1 1.240(5) . ?
S1 C7 1.637(5) . ?
S1 C4 1.646(5) . ?
S1' C4 1.623(6) . ?
S1' C6 1.624(6) . ?
C2 C3 1.494(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.489(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.400(9) . ?
C4 C5' 1.415(10) . ?
C5 C6 1.427(8) . ?
C5 H5 0.9300 . ?
C5' C7 1.420(9) . ?
C5' H5' 0.9300 . ?
C6 C7 1.354(6) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.389(5) . ?
C8 C13 1.393(6) . ?
C9 C10 1.375(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.370(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.372(6) . ?
C12 H12 0.9300 . ?
C13 H13 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
C1 N1 C2 123.0(4) . . ?
C1 N1 H1 118.5 . . ?
C2 N1 H1 118.5 . . ?
C1 N2 C8 126.3(4) . . ?
C1 N2 H2 116.8 . . ?
C8 N2 H2 116.8 . . ?
C7 S1 C4 95.2(3) . . ?
C4 S1' C6 95.3(3) . . ?
O1 C1 N1 122.5(4) . . ?
O1 C1 N2 123.4(4) . . ?
N1 C1 N2 114.0(4) . . ?
N1 C2 C3 113.1(4) . . ?
N1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
N1 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 C2 113.0(4) . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C5 C4 C5' 96.0(7) . . ?
C5 C4 C3 130.6(5) . . ?
C5' C4 C3 133.1(6) . . ?
C5 C4 S1' 10.1(5) . . ?
C5' C4 S1' 106.1(6) . . ?
C3 C4 S1' 120.5(4) . . ?
C5 C4 S1 107.1(5) . . ?
C5' C4 S1 11.7(7) . . ?
C3 C4 S1 122.2(4) . . ?
S1' C4 S1 117.2(3) . . ?
C4 C5 C6 116.1(8) . . ?
C4 C5 H5 121.9 . . ?
C6 C5 H5 121.9 . . ?
C4 C5' C7 117.6(9) . . ?
C4 C5' H5' 121.2 . . ?
C7 C5' H5' 121.2 . . ?
C7 C6 C5 106.3(6) . . ?
C7 C6 S1' 117.0(4) . . ?
C5 C6 S1' 10.8(5) . . ?
C7 C6 H6 126.9 . . ?
C5 C6 H6 126.9 . . ?
S1' C6 H6 116.1 . . ?
C6 C7 C5' 103.7(6) . . ?
C6 C7 S1 115.3(4) . . ?
C5' C7 S1 12.1(7) . . ?
C6 C7 H7 122.4 . . ?
C5' C7 H7 133.8 . . ?
S1 C7 H7 122.4 . . ?
C9 C8 C13 117.9(4) . . ?
C9 C8 N2 124.2(4) . . ?
C13 C8 N2 117.8(4) . . ?
C10 C9 C8 120.3(4) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 121.1(5) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 119.3(5) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C13 C12 C11 120.3(5) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C8 121.1(4) . . ?
C12 C13 H13 119.5 . . ?
C8 C13 H13 119.5 . . ?

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
C2 N1 C1 O1 6.6(6) . . . . ?
C2 N1 C1 N2 -172.9(3) . . . . ?
C8 N2 C1 O1 8.0(6) . . . . ?
C8 N2 C1 N1 -172.5(4) . . . . ?
C1 N1 C2 C3 -97.5(5) . . . . ?
N1 C2 C3 C4 177.8(4) . . . . ?
C2 C3 C4 C5 80.1(13) . . . . ?
C2 C3 C4 C5' -90.9(19) . . . . ?
C2 C3 C4 S1' 81.6(6) . . . . ?
C2 C3 C4 S1 -96.5(6) . . . . ?
C6 S1' C4 C5 -4(6) . . . . ?
C6 S1' C4 C5' -3.6(16) . . . . ?
C6 S1' C4 C3 -177.8(4) . . . . ?
C6 S1' C4 S1 0.3(5) . . . . ?
C7 S1 C4 C5 0.0(11) . . . . ?
C7 S1 C4 C5' 18(7) . . . . ?
C7 S1 C4 C3 177.3(4) . . . . ?
C7 S1 C4 S1' -0.8(5) . . . . ?
C5' C4 C5 C6 -4.7(15) . . . . ?
C3 C4 C5 C6 -178.1(7) . . . . ?
S1' C4 C5 C6 175(8) . . . . ?
S1 C4 C5 C6 -1.1(18) . . . . ?
C5 C4 C5' C7 6(2) . . . . ?
C3 C4 C5' C7 179.4(10) . . . . ?
S1' C4 C5' C7 6(3) . . . . ?
S1 C4 C5' C7 -157(9) . . . . ?
C4 C5 C6 C7 1.8(17) . . . . ?
C4 C5 C6 S1' -175(7) . . . . ?
C4 S1' C6 C7 0.5(7) . . . . ?
C4 S1' C6 C5 4(6) . . . . ?
C5 C6 C7 C5' 2.1(19) . . . . ?
S1' C6 C7 C5' 2.8(13) . . . . ?
C5 C6 C7 S1 -1.8(10) . . . . ?
S1' C6 C7 S1 -1.1(8) . . . . ?
C4 C5' C7 C6 -6(2) . . . . ?
C4 C5' C7 S1 157(8) . . . . ?
C4 S1 C7 C6 1.1(6) . . . . ?
C4 S1 C7 C5' -17(6) . . . . ?
C1 N2 C8 C9 25.0(6) . . . . ?
C1 N2 C8 C13 -158.1(4) . . . . ?
C13 C8 C9 C10 0.7(6) . . . . ?
N2 C8 C9 C10 177.6(4) . . . . ?
C8 C9 C10 C11 -1.4(7) . . . . ?
C9 C10 C11 C12 0.4(8) . . . . ?
C10 C11 C12 C13 1.4(8) . . . . ?
C11 C12 C13 C8 -2.1(8) . . . . ?
C9 C8 C13 C12 1.1(6) . . . . ?
N2 C8 C13 C12 -176.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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_180715c
_database_code_depnum_ccdc_archive 'CCDC 1966547'
loop_
_audit_author_name
_audit_author_address
'Bruker '
;Liaocheng University
China
;
_audit_update_record             
;
2019-11-19 deposited with the CCDC.	2020-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H14 N2 O2'
_chemical_formula_weight         206.24

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'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   8.1026(7)
_cell_length_b                   15.7929(13)
_cell_length_c                   8.4783(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.183(3)
_cell_angle_gamma                90.00
_cell_volume                     1051.84(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2511
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      28.328

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.38
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9585
_exptl_absorpt_correction_T_max  0.9662
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5082
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.58
_diffrn_reflns_theta_max         25.02
_reflns_number_total             1854
_reflns_number_gt                1457
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0483P)²+0.2205P] where P=(Fo²+2Fc²)/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       0.083(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1854
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.1027
_refine_ls_wR_factor_gt          0.0929
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
N1 N 0.67243(17) 0.63200(9) 0.52321(15) 0.0443(4) Uani 1 1 d . . .
N2 N 0.47260(16) 0.73916(8) 0.50105(15) 0.0419(3) Uani 1 1 d . . .
H2 H 0.5033 0.7555 0.4158 0.050 Uiso 1 1 calc R . .
O1 O 0.55757(13) 0.66192(7) 0.73503(12) 0.0433(3) Uani 1 1 d . . .
O2 O 0.79321(15) 0.49468(8) 0.36939(16) 0.0570(4) Uani 1 1 d . . .
C1 C 0.56717(17) 0.67663(9) 0.59448(18) 0.0345(4) Uani 1 1 d . . .
C2 C 0.79455(19) 0.57180(10) 0.6175(2) 0.0463(4) Uani 1 1 d . . .
H2A H 0.7742 0.5652 0.7249 0.056 Uiso 1 1 calc R . .
H2B H 0.9093 0.5932 0.6303 0.056 Uiso 1 1 calc R . .
C3 C 0.7775(2) 0.48728(11) 0.5327(2) 0.0533(5) Uani 1 1 d . . .
H3A H 0.8648 0.4493 0.5924 0.064 Uiso 1 1 calc R . .
H3B H 0.6676 0.4629 0.5324 0.064 Uiso 1 1 calc R . .
C4 C 0.6657(2) 0.54936(11) 0.2804(2) 0.0530(5) Uani 1 1 d . . .
H4A H 0.5546 0.5259 0.2784 0.064 Uiso 1 1 calc R . .
H4B H 0.6761 0.5530 0.1690 0.064 Uiso 1 1 calc R . .
C5 C 0.6788(2) 0.63678(11) 0.3529(2) 0.0519(5) Uani 1 1 d . . .
H5A H 0.7848 0.6629 0.3450 0.062 Uiso 1 1 calc R . .
H5B H 0.5856 0.6715 0.2929 0.062 Uiso 1 1 calc R . .
C6 C 0.32844(18) 0.77853(9) 0.53523(17) 0.0356(4) Uani 1 1 d . . .
C7 C 0.2934(2) 0.86165(10) 0.48424(19) 0.0446(4) Uani 1 1 d . . .
H7 H 0.3677 0.8908 0.4358 0.053 Uiso 1 1 calc R . .
C8 C 0.1484(2) 0.90083(12) 0.5055(2) 0.0585(5) Uani 1 1 d . . .
H8 H 0.1243 0.9561 0.4692 0.070 Uiso 1 1 calc R . .
C9 C 0.0390(2) 0.85912(12) 0.5798(3) 0.0635(5) Uani 1 1 d . . .
H9 H -0.0580 0.8861 0.5947 0.076 Uiso 1 1 calc R . .
C10 C 0.0742(2) 0.77689(12) 0.6321(2) 0.0531(5) Uani 1 1 d . . .
H10 H 0.0015 0.7488 0.6840 0.064 Uiso 1 1 calc R . .
C11 C 0.21682(19) 0.73588(10) 0.60793(19) 0.0424(4) Uani 1 1 d . . .
H11 H 0.2379 0.6798 0.6403 0.051 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
N1 0.0517(8) 0.0445(8) 0.0407(7) 0.0029(6) 0.0191(6) 0.0171(6)
N2 0.0508(7) 0.0414(7) 0.0403(7) 0.0095(6) 0.0242(6) 0.0154(6)
O1 0.0530(7) 0.0436(6) 0.0369(6) 0.0034(5) 0.0177(5) 0.0100(5)
O2 0.0531(7) 0.0507(7) 0.0705(8) -0.0123(6) 0.0216(6) 0.0114(6)
C1 0.0374(8) 0.0302(8) 0.0379(8) -0.0026(6) 0.0133(6) 0.0007(6)
C2 0.0399(8) 0.0483(10) 0.0511(10) 0.0006(7) 0.0116(7) 0.0113(7)
C3 0.0462(9) 0.0437(10) 0.0713(12) 0.0024(8) 0.0169(8) 0.0090(7)
C4 0.0487(9) 0.0605(11) 0.0531(10) -0.0089(9) 0.0190(8) 0.0076(8)
C5 0.0656(11) 0.0504(10) 0.0474(10) 0.0031(8) 0.0287(8) 0.0154(8)
C6 0.0426(8) 0.0362(8) 0.0297(7) -0.0014(6) 0.0120(6) 0.0078(6)
C7 0.0535(9) 0.0380(9) 0.0468(9) 0.0060(7) 0.0211(7) 0.0081(7)
C8 0.0701(12) 0.0413(10) 0.0714(12) 0.0133(9) 0.0314(10) 0.0214(9)
C9 0.0586(11) 0.0599(12) 0.0819(13) 0.0111(10) 0.0359(10) 0.0253(9)
C10 0.0493(10) 0.0547(11) 0.0618(11) 0.0051(8) 0.0259(8) 0.0045(8)
C11 0.0488(9) 0.0361(8) 0.0444(9) 0.0021(7) 0.0158(7) 0.0048(7)

_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
N1 C1 1.3571(18) . ?
N1 C5 1.4594(19) . ?
N1 C2 1.461(2) . ?
N2 C1 1.3757(18) . ?
N2 C6 1.4145(18) . ?
N2 H2 0.8600 . ?
O1 C1 1.2350(17) . ?
O2 C4 1.414(2) . ?
O2 C3 1.426(2) . ?
C2 C3 1.506(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.504(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C11 1.387(2) . ?
C6 C7 1.389(2) . ?
C7 C8 1.378(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.375(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.379(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.383(2) . ?
C10 H10 0.9300 . ?
C11 H11 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
C1 N1 C5 126.30(13) . . ?
C1 N1 C2 120.63(13) . . ?
C5 N1 C2 113.07(12) . . ?
C1 N2 C6 124.68(12) . . ?
C1 N2 H2 117.7 . . ?
C6 N2 H2 117.7 . . ?
C4 O2 C3 109.94(12) . . ?
O1 C1 N1 121.80(13) . . ?
O1 C1 N2 122.19(12) . . ?
N1 C1 N2 116.01(13) . . ?
N1 C2 C3 110.18(13) . . ?
N1 C2 H2A 109.6 . . ?
C3 C2 H2A 109.6 . . ?
N1 C2 H2B 109.6 . . ?
C3 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
O2 C3 C2 111.79(14) . . ?
O2 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
O2 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
O2 C4 C5 111.93(14) . . ?
O2 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
O2 C4 H4B 109.2 . . ?
C5 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
N1 C5 C4 109.93(14) . . ?
N1 C5 H5A 109.7 . . ?
C4 C5 H5A 109.7 . . ?
N1 C5 H5B 109.7 . . ?
C4 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
C11 C6 C7 119.40(13) . . ?
C11 C6 N2 122.58(13) . . ?
C7 C6 N2 117.89(13) . . ?
C8 C7 C6 119.97(15) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C9 C8 C7 120.72(16) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 119.52(15) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C11 120.51(16) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C6 119.85(15) . . ?
C10 C11 H11 120.1 . . ?
C6 C11 H11 120.1 . . ?

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
C5 N1 C1 O1 171.96(15) . . . . ?
C2 N1 C1 O1 -7.8(2) . . . . ?
C5 N1 C1 N2 -8.2(2) . . . . ?
C2 N1 C1 N2 172.02(14) . . . . ?
C6 N2 C1 O1 -16.1(2) . . . . ?
C6 N2 C1 N1 164.04(14) . . . . ?
C1 N1 C2 C3 128.51(15) . . . . ?
C5 N1 C2 C3 -51.28(18) . . . . ?
C4 O2 C3 C2 -59.45(17) . . . . ?
N1 C2 C3 O2 54.73(17) . . . . ?
C3 O2 C4 C5 60.08(18) . . . . ?
C1 N1 C5 C4 -128.14(16) . . . . ?
C2 N1 C5 C4 51.63(19) . . . . ?
O2 C4 C5 N1 -55.92(18) . . . . ?
C1 N2 C6 C11 -33.3(2) . . . . ?
C1 N2 C6 C7 150.70(15) . . . . ?
C11 C6 C7 C8 -0.3(2) . . . . ?
N2 C6 C7 C8 175.86(15) . . . . ?
C6 C7 C8 C9 1.3(3) . . . . ?
C7 C8 C9 C10 -0.6(3) . . . . ?
C8 C9 C10 C11 -1.1(3) . . . . ?
C9 C10 C11 C6 2.1(3) . . . . ?
C7 C6 C11 C10 -1.4(2) . . . . ?
N2 C6 C11 C10 -177.32(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.043
