# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_mo_Di_sub_bzx_ta_3_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2131761'
loop_
_audit_author_name
_audit_author_address
'SOURAV MUKHERJEE'
;SHIV NADAR UNIVERSITY
India
;
_audit_update_record             
;
2021-12-30 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
2,4-diphenyl-3-(thiophen-2-ylmethyl)-3,4-dihydro-2H-benzo[e][1,3]oxazine
_chemical_name_common            PH-ta-[2,4]-Ph
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H21 N O S'
_chemical_formula_sum            'C25 H21 N O S'
_chemical_formula_weight         383.49

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                   11.598(6)
_cell_length_b                   9.723(6)
_cell_length_c                   18.055(11)
_cell_angle_alpha                90
_cell_angle_beta                 99.760(18)
_cell_angle_gamma                90
_cell_volume                     2007(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    289(2)
_cell_measurement_reflns_used    8559
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      24.48

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_F_000             988
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.176
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.6508
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      289(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31861
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.289
_diffrn_reflns_theta_max         26.665
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4145
_reflns_number_gt                2893
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0815P)²+0.5219P] 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         4145
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1699
_refine_ls_wR_factor_gt          0.1491
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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 0.11222(7) 0.49685(7) 0.74145(4) 0.0843(3) Uani 1 1 d . . . . .
O1 O 0.43890(13) 0.62074(18) 0.57248(8) 0.0715(4) Uani 1 1 d . . . . .
N1 N 0.27804(14) 0.51399(17) 0.61917(9) 0.0569(4) Uani 1 1 d . . . . .
C21 C 0.24276(19) 0.6428(2) 0.65228(12) 0.0610(5) Uani 1 1 d . . . . .
H21A H 0.234876 0.715197 0.614795 0.073 Uiso 1 1 calc R U . . .
H21B H 0.302891 0.670173 0.693753 0.073 Uiso 1 1 calc R U . . .
C2 C 0.20261(17) 0.3398(2) 0.52308(11) 0.0573(5) Uani 1 1 d . . . . .
C1 C 0.21037(18) 0.4925(2) 0.54300(11) 0.0575(5) Uani 1 1 d . . . . .
H1 H 0.130345 0.523084 0.544715 0.069 Uiso 1 1 calc R U . . .
C13 C 0.36617(19) 0.6449(2) 0.50545(12) 0.0633(5) Uani 1 1 d . . . . .
C22 C 0.12936(19) 0.6248(2) 0.67985(11) 0.0581(5) Uani 1 1 d . . . . .
C7 C 0.13168(19) 0.2535(3) 0.55808(13) 0.0677(6) Uani 1 1 d . . . . .
H7 H 0.091870 0.289152 0.594346 0.081 Uiso 1 1 calc R U . . .
C23 C 0.02826(18) 0.7050(2) 0.66209(13) 0.0662(6) Uani 1 1 d . . . . .
H23 H 0.019230 0.778589 0.628727 0.079 Uiso 1 1 calc R U . . .
C3 C 0.2620(2) 0.2821(2) 0.47083(13) 0.0678(6) Uani 1 1 d . . . . .
H3 H 0.310054 0.336888 0.446802 0.081 Uiso 1 1 calc R U . . .
C8 C 0.25608(19) 0.5842(2) 0.48755(11) 0.0607(5) Uani 1 1 d . . . . .
C14 C 0.40131(19) 0.5082(2) 0.61542(12) 0.0632(5) Uani 1 1 d . . . . .
H14 H 0.415739 0.422291 0.590133 0.076 Uiso 1 1 calc R U . . .
C15 C 0.47785(19) 0.5078(2) 0.69197(13) 0.0656(6) Uani 1 1 d . . . . .
C4 C 0.2510(2) 0.1436(3) 0.45372(15) 0.0779(7) Uani 1 1 d . . . . .
H4 H 0.292576 0.105894 0.418917 0.093 Uiso 1 1 calc R U . . .
C12 C 0.4056(2) 0.7379(3) 0.45707(14) 0.0736(6) Uani 1 1 d . . . . .
H12 H 0.478064 0.780323 0.470409 0.088 Uiso 1 1 calc R U . . .
C9 C 0.1887(2) 0.6167(2) 0.41873(13) 0.0712(6) Uani 1 1 d . . . . .
H9 H 0.115105 0.577033 0.405663 0.085 Uiso 1 1 calc R U . . .
C5 C 0.1798(2) 0.0623(3) 0.48740(15) 0.0809(7) Uani 1 1 d . . . . .
H5 H 0.171528 -0.030477 0.475043 0.097 Uiso 1 1 calc R U . . .
C6 C 0.1202(2) 0.1176(3) 0.53965(16) 0.0827(7) Uani 1 1 d . . . . .
H6 H 0.071580 0.061998 0.562756 0.099 Uiso 1 1 calc R U . . .
C24 C -0.0598(2) 0.6563(3) 0.70328(16) 0.0821(7) Uani 1 1 d . . . . .
H24 H -0.133536 0.696001 0.699382 0.099 Uiso 1 1 calc R U . . .
C10 C 0.2275(3) 0.7059(3) 0.36942(14) 0.0847(8) Uani 1 1 d . . . . .
H10 H 0.181253 0.725186 0.323309 0.102 Uiso 1 1 calc R U . . .
C11 C 0.3363(3) 0.7667(3) 0.38909(15) 0.0838(7) Uani 1 1 d . . . . .
H11 H 0.362903 0.827604 0.356022 0.101 Uiso 1 1 calc R U . . .
C25 C -0.0252(2) 0.5483(3) 0.74776(16) 0.0846(7) Uani 1 1 d . . . . .
H25 H -0.071550 0.506398 0.778570 0.102 Uiso 1 1 calc R U . . .
C16 C 0.5846(2) 0.5775(4) 0.70694(15) 0.0912(8) Uani 1 1 d . . . . .
H16 H 0.611843 0.627087 0.669357 0.109 Uiso 1 1 calc R U . . .
C18 C 0.6140(3) 0.4993(4) 0.83309(17) 0.0958(9) Uani 1 1 d . . . . .
H18 H 0.658647 0.498765 0.881021 0.115 Uiso 1 1 calc R U . . .
C20 C 0.4458(3) 0.4306(3) 0.74897(16) 0.0951(9) Uani 1 1 d . . . . .
H20 H 0.376752 0.379991 0.740075 0.114 Uiso 1 1 calc R U . . .
C19 C 0.5146(3) 0.4273(4) 0.81909(18) 0.1109(11) Uani 1 1 d . . . . .
H19 H 0.491597 0.374474 0.856999 0.133 Uiso 1 1 calc R U . . .
C17 C 0.6491(3) 0.5715(4) 0.77880(18) 0.1105(11) Uani 1 1 d . . . . .
H17 H 0.719270 0.619645 0.789282 0.133 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 C25 1.693(3) . ?
S1 C22 1.703(2) . ?
O1 C13 1.373(3) . ?
O1 C14 1.450(3) . ?
N1 C14 1.444(3) . ?
N1 C21 1.475(3) . ?
N1 C1 1.478(3) . ?
C21 C22 1.493(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C2 C3 1.379(3) . ?
C2 C7 1.399(3) . ?
C2 C1 1.527(3) . ?
C1 C8 1.503(3) . ?
C1 H1 0.9800 . ?
C13 C12 1.388(3) . ?
C13 C8 1.394(3) . ?
C22 C23 1.399(3) . ?
C7 C6 1.363(4) . ?
C7 H7 0.9300 . ?
C23 C24 1.441(3) . ?
C23 H23 0.9300 . ?
C3 C4 1.382(4) . ?
C3 H3 0.9300 . ?
C8 C9 1.388(3) . ?
C14 C15 1.511(3) . ?
C14 H14 0.9800 . ?
C15 C20 1.375(4) . ?
C15 C16 1.398(4) . ?
C4 C5 1.359(4) . ?
C4 H4 0.9300 . ?
C12 C11 1.377(4) . ?
C12 H12 0.9300 . ?
C9 C10 1.372(4) . ?
C9 H9 0.9300 . ?
C5 C6 1.370(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C24 C25 1.342(4) . ?
C24 H24 0.9300 . ?
C10 C11 1.384(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C25 H25 0.9300 . ?
C16 C17 1.385(4) . ?
C16 H16 0.9300 . ?
C18 C17 1.324(5) . ?
C18 C19 1.337(5) . ?
C18 H18 0.9300 . ?
C20 C19 1.378(4) . ?
C20 H20 0.9300 . ?
C19 H19 0.9300 . ?
C17 H17 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
C25 S1 C22 92.50(13) . . ?
C13 O1 C14 113.88(17) . . ?
C14 N1 C21 113.38(16) . . ?
C14 N1 C1 108.95(16) . . ?
C21 N1 C1 110.91(16) . . ?
N1 C21 C22 110.87(17) . . ?
N1 C21 H21A 109.5 . . ?
C22 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 108.1 . . ?
C3 C2 C7 117.7(2) . . ?
C3 C2 C1 122.8(2) . . ?
C7 C2 C1 119.53(19) . . ?
N1 C1 C8 110.15(17) . . ?
N1 C1 C2 110.94(16) . . ?
C8 C1 C2 115.67(17) . . ?
N1 C1 H1 106.5 . . ?
C8 C1 H1 106.5 . . ?
C2 C1 H1 106.5 . . ?
O1 C13 C12 116.6(2) . . ?
O1 C13 C8 122.2(2) . . ?
C12 C13 C8 121.1(2) . . ?
C23 C22 C21 127.6(2) . . ?
C23 C22 S1 111.75(17) . . ?
C21 C22 S1 120.67(16) . . ?
C6 C7 C2 120.8(2) . . ?
C6 C7 H7 119.6 . . ?
C2 C7 H7 119.6 . . ?
C22 C23 C24 109.8(2) . . ?
C22 C23 H23 125.1 . . ?
C24 C23 H23 125.1 . . ?
C2 C3 C4 120.8(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C9 C8 C13 117.7(2) . . ?
C9 C8 C1 121.6(2) . . ?
C13 C8 C1 120.63(18) . . ?
N1 C14 O1 112.68(17) . . ?
N1 C14 C15 112.96(18) . . ?
O1 C14 C15 107.94(18) . . ?
N1 C14 H14 107.7 . . ?
O1 C14 H14 107.7 . . ?
C15 C14 H14 107.7 . . ?
C20 C15 C16 117.6(2) . . ?
C20 C15 C14 119.6(2) . . ?
C16 C15 C14 122.7(2) . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C11 C12 C13 119.2(2) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C10 C9 C8 121.9(2) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C4 C5 C6 119.6(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C7 C6 C5 120.6(3) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C25 C24 C23 113.6(2) . . ?
C25 C24 H24 123.2 . . ?
C23 C24 H24 123.2 . . ?
C9 C10 C11 119.2(2) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C12 C11 C10 120.7(2) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C24 C25 S1 112.3(2) . . ?
C24 C25 H25 123.8 . . ?
S1 C25 H25 123.8 . . ?
C17 C16 C15 118.7(3) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C17 C18 C19 120.1(3) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C15 C20 C19 120.8(3) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C18 C19 C20 120.6(3) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C18 C17 C16 122.1(3) . . ?
C18 C17 H17 119.0 . . ?
C16 C17 H17 119.0 . . ?

_refine_diff_density_max         0.239
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.036


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 2% ethylacetate in hexane'
