# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_yjx204
_audit_block_doi                 10.5517/ccdc.csd.cc21x8nx
_database_code_depnum_ccdc_archive 'CCDC 1904009'
loop_
_audit_author_name
_audit_author_address
'jiangxi yu'
;Hengyang normal university
China
;
_audit_update_record             
;
2019-03-19 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
3a,5,8-trimethyl-1-phenyl-3,3a-dihydrothieno[3,4-c]quinolin-4(5H)-one
_chemical_name_common            ?
_chemical_melting_point          436
_chemical_formula_moiety         'C20 H19 N O S'
_chemical_formula_sum            'C20 H19 N O S'
_chemical_formula_weight         321.42

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   12.2921(15)
_cell_length_b                   13.3688(17)
_cell_length_c                   10.0405(12)
_cell_angle_alpha                90
_cell_angle_beta                 101.103(2)
_cell_angle_gamma                90
_cell_volume                     1619.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2525
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      25.61

_exptl_crystal_description       lump
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   0.958
_exptl_transmission_factor_max   0.966
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.204
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9188
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.688
_diffrn_reflns_theta_max         26.572
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3367
_reflns_number_gt                2525
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0507P)²+0.4365P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3367
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1183
_refine_ls_wR_factor_gt          0.1054
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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_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 0.60907(4) 0.41043(4) -0.01952(5) 0.04669(17) Uani 1 1 d . . . . .
O1 O 0.88269(15) 0.64435(12) 0.09141(15) 0.0664(5) Uani 1 1 d . . . . .
N1 N 0.86480(13) 0.61249(11) 0.30697(16) 0.0387(4) Uani 1 1 d . . . . .
C1 C 0.85034(16) 0.58938(14) 0.1724(2) 0.0418(4) Uani 1 1 d . . . . .
C2 C 0.79334(15) 0.49097(14) 0.12552(17) 0.0358(4) Uani 1 1 d . . . . .
C3 C 0.71405(17) 0.50689(16) -0.01053(19) 0.0464(5) Uani 1 1 d . . . . .
H3A H 0.753187 0.500409 -0.085251 0.056 Uiso 1 1 calc R U . . .
H3B H 0.680630 0.572810 -0.014190 0.056 Uiso 1 1 calc R U . . .
C4 C 0.62531(14) 0.41137(13) 0.15960(17) 0.0351(4) Uani 1 1 d . . . . .
C5 C 0.72105(14) 0.45366(13) 0.22152(17) 0.0329(4) Uani 1 1 d . . . . .
C6 C 0.76774(13) 0.46371(13) 0.36646(17) 0.0320(4) Uani 1 1 d . . . . .
C7 C 0.74920(14) 0.39604(13) 0.46535(17) 0.0347(4) Uani 1 1 d . . . . .
H7 H 0.704589 0.340591 0.438831 0.042 Uiso 1 1 calc R U . . .
C8 C 0.79474(15) 0.40833(14) 0.60155(18) 0.0382(4) Uani 1 1 d . . . . .
C9 C 0.86077(16) 0.49160(16) 0.63815(19) 0.0451(5) Uani 1 1 d . . . . .
H9 H 0.890467 0.502531 0.729378 0.054 Uiso 1 1 calc R U . . .
C10 C 0.88376(15) 0.55901(15) 0.54257(19) 0.0428(5) Uani 1 1 d . . . . .
H10 H 0.929405 0.613646 0.570072 0.051 Uiso 1 1 calc R U . . .
C11 C 0.83907(14) 0.54547(14) 0.40602(18) 0.0349(4) Uani 1 1 d . . . . .
C12 C 0.92126(19) 0.70670(15) 0.3517(2) 0.0543(6) Uani 1 1 d . . . . .
H12A H 0.995879 0.692949 0.397040 0.081 Uiso 1 1 calc R U . . .
H12B H 0.882402 0.740281 0.412973 0.081 Uiso 1 1 calc R U . . .
H12C H 0.922473 0.748575 0.274302 0.081 Uiso 1 1 calc R U . . .
C13 C 0.88358(16) 0.41382(15) 0.1128(2) 0.0448(5) Uani 1 1 d . . . . .
H13A H 0.923095 0.396011 0.201684 0.067 Uiso 1 1 calc R U . . .
H13B H 0.934230 0.442103 0.061366 0.067 Uiso 1 1 calc R U . . .
H13C H 0.849741 0.355178 0.067529 0.067 Uiso 1 1 calc R U . . .
C14 C 0.53355(14) 0.37007(14) 0.21885(17) 0.0363(4) Uani 1 1 d . . . . .
C15 C 0.48572(16) 0.27864(16) 0.1763(2) 0.0480(5) Uani 1 1 d . . . . .
H15 H 0.512805 0.241757 0.111205 0.058 Uiso 1 1 calc R U . . .
C16 C 0.39826(18) 0.24191(18) 0.2298(3) 0.0595(6) Uani 1 1 d . . . . .
H16 H 0.367274 0.180295 0.200950 0.071 Uiso 1 1 calc R U . . .
C17 C 0.35674(18) 0.29582(18) 0.3252(2) 0.0563(6) Uani 1 1 d . . . . .
H17 H 0.298193 0.270675 0.361544 0.068 Uiso 1 1 calc R U . . .
C18 C 0.40252(17) 0.38762(18) 0.3669(2) 0.0496(5) Uani 1 1 d . . . . .
H18 H 0.374184 0.424671 0.430832 0.059 Uiso 1 1 calc R U . . .
C19 C 0.48999(15) 0.42460(16) 0.31421(19) 0.0426(5) Uani 1 1 d . . . . .
H19 H 0.520135 0.486575 0.342704 0.051 Uiso 1 1 calc R U . . .
C20 C 0.7716(2) 0.33518(17) 0.7065(2) 0.0539(6) Uani 1 1 d . . . . .
H20A H 0.709743 0.358250 0.743592 0.081 Uiso 1 1 calc R U . . .
H20B H 0.835747 0.329714 0.777831 0.081 Uiso 1 1 calc R U . . .
H20C H 0.754683 0.270880 0.665136 0.081 Uiso 1 1 calc R U . . .


_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 C4 1.7709(18) . ?
S1 C3 1.814(2) . ?
O1 C1 1.218(2) . ?
N1 C1 1.364(2) . ?
N1 C11 1.419(2) . ?
N1 C12 1.466(2) . ?
C1 C2 1.522(3) . ?
C2 C5 1.516(2) . ?
C2 C3 1.532(3) . ?
C2 C13 1.538(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.345(2) . ?
C4 C14 1.480(2) . ?
C5 C6 1.464(2) . ?
C6 C7 1.394(2) . ?
C6 C11 1.410(2) . ?
C7 C8 1.384(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.385(3) . ?
C8 C20 1.504(3) . ?
C9 C10 1.385(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.387(2) . ?
C10 H10 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.388(3) . ?
C14 C19 1.390(2) . ?
C15 C16 1.381(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.374(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.381(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.378(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
C4 S1 C3 90.25(9) . . ?
C1 N1 C11 123.18(15) . . ?
C1 N1 C12 117.49(16) . . ?
C11 N1 C12 118.96(16) . . ?
O1 C1 N1 121.85(18) . . ?
O1 C1 C2 120.32(17) . . ?
N1 C1 C2 117.82(16) . . ?
C5 C2 C1 112.27(15) . . ?
C5 C2 C3 105.22(15) . . ?
C1 C2 C3 109.36(15) . . ?
C5 C2 C13 110.64(15) . . ?
C1 C2 C13 108.00(15) . . ?
C3 C2 C13 111.37(16) . . ?
C2 C3 S1 105.65(13) . . ?
C2 C3 H3A 110.6 . . ?
S1 C3 H3A 110.6 . . ?
C2 C3 H3B 110.6 . . ?
S1 C3 H3B 110.6 . . ?
H3A C3 H3B 108.7 . . ?
C5 C4 C14 129.63(16) . . ?
C5 C4 S1 112.94(13) . . ?
C14 C4 S1 117.40(12) . . ?
C4 C5 C6 129.68(16) . . ?
C4 C5 C2 114.35(15) . . ?
C6 C5 C2 115.87(14) . . ?
C7 C6 C11 118.72(16) . . ?
C7 C6 C5 124.19(16) . . ?
C11 C6 C5 117.05(15) . . ?
C8 C7 C6 122.43(17) . . ?
C8 C7 H7 118.8 . . ?
C6 C7 H7 118.8 . . ?
C7 C8 C9 117.54(17) . . ?
C7 C8 C20 121.33(17) . . ?
C9 C8 C20 121.11(17) . . ?
C10 C9 C8 121.78(17) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C9 C10 C11 120.35(17) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C6 119.09(17) . . ?
C10 C11 N1 120.74(16) . . ?
C6 C11 N1 120.17(16) . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 118.51(17) . . ?
C15 C14 C4 121.03(17) . . ?
C19 C14 C4 120.39(17) . . ?
C16 C15 C14 120.6(2) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 119.5(2) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C19 C18 C17 120.3(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C14 120.58(19) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
C8 C20 H20A 109.5 . . ?
C8 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C8 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C11 N1 C1 O1 -172.95(18) . . . . ?
C12 N1 C1 O1 0.0(3) . . . . ?
C11 N1 C1 C2 6.2(3) . . . . ?
C12 N1 C1 C2 179.11(17) . . . . ?
O1 C1 C2 C5 -157.58(18) . . . . ?
N1 C1 C2 C5 23.3(2) . . . . ?
O1 C1 C2 C3 -41.2(2) . . . . ?
N1 C1 C2 C3 139.67(17) . . . . ?
O1 C1 C2 C13 80.2(2) . . . . ?
N1 C1 C2 C13 -98.98(19) . . . . ?
C5 C2 C3 S1 -33.86(17) . . . . ?
C1 C2 C3 S1 -154.66(13) . . . . ?
C13 C2 C3 S1 86.05(16) . . . . ?
C4 S1 C3 C2 30.06(14) . . . . ?
C3 S1 C4 C5 -18.34(16) . . . . ?
C3 S1 C4 C14 159.78(15) . . . . ?
C14 C4 C5 C6 6.0(3) . . . . ?
S1 C4 C5 C6 -176.16(15) . . . . ?
C14 C4 C5 C2 -177.78(17) . . . . ?
S1 C4 C5 C2 0.1(2) . . . . ?
C1 C2 C5 C4 141.49(17) . . . . ?
C3 C2 C5 C4 22.6(2) . . . . ?
C13 C2 C5 C4 -97.77(19) . . . . ?
C1 C2 C5 C6 -41.7(2) . . . . ?
C3 C2 C5 C6 -160.61(15) . . . . ?
C13 C2 C5 C6 78.99(19) . . . . ?
C4 C5 C6 C7 30.1(3) . . . . ?
C2 C5 C6 C7 -146.07(17) . . . . ?
C4 C5 C6 C11 -152.35(19) . . . . ?
C2 C5 C6 C11 31.5(2) . . . . ?
C11 C6 C7 C8 2.6(3) . . . . ?
C5 C6 C7 C8 -179.87(16) . . . . ?
C6 C7 C8 C9 0.0(3) . . . . ?
C6 C7 C8 C20 178.83(18) . . . . ?
C7 C8 C9 C10 -1.9(3) . . . . ?
C20 C8 C9 C10 179.29(18) . . . . ?
C8 C9 C10 C11 1.1(3) . . . . ?
C9 C10 C11 C6 1.6(3) . . . . ?
C9 C10 C11 N1 -178.11(17) . . . . ?
C7 C6 C11 C10 -3.4(3) . . . . ?
C5 C6 C11 C10 178.90(16) . . . . ?
C7 C6 C11 N1 176.35(15) . . . . ?
C5 C6 C11 N1 -1.3(2) . . . . ?
C1 N1 C11 C10 161.02(18) . . . . ?
C12 N1 C11 C10 -11.8(3) . . . . ?
C1 N1 C11 C6 -18.7(3) . . . . ?
C12 N1 C11 C6 168.45(17) . . . . ?
C5 C4 C14 C15 -134.8(2) . . . . ?
S1 C4 C14 C15 47.5(2) . . . . ?
C5 C4 C14 C19 48.2(3) . . . . ?
S1 C4 C14 C19 -129.53(16) . . . . ?
C19 C14 C15 C16 -1.3(3) . . . . ?
C4 C14 C15 C16 -178.35(19) . . . . ?
C14 C15 C16 C17 0.5(4) . . . . ?
C15 C16 C17 C18 0.5(4) . . . . ?
C16 C17 C18 C19 -0.6(3) . . . . ?
C17 C18 C19 C14 -0.2(3) . . . . ?
C15 C14 C19 C18 1.1(3) . . . . ?
C4 C14 C19 C18 178.21(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H12B O1 0.96 2.36 3.229(3) 149.6 4_576

_refine_diff_density_max         0.197
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.043

