# 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_twin5
_database_code_depnum_ccdc_archive 'CCDC 1937210'
loop_
_audit_author_name
_audit_author_address
'Folkert de Vries'
;University of Groningen
Netherlands
;
_audit_update_record             
;
2019-06-28 deposited with the CCDC.	2019-09-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT906_twin5               
;
PROBLEM: Large K Value in the Analysis of Variance ......      2.043 Check
RESPONSE: Data reduction and refinement was complicated due to twinning, which is the likely source of the large K value in the analysis of variance
;
# Added during the CSD deposition process: Friday 28 June 2019 04:44 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
2-(1-(benzo[d][1,3]dithiol-2-yl)-2-phenylbutyl)benzo[d]oxazole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H21 N O S2'
_chemical_formula_sum            'C24 H21 N O S2'
_chemical_formula_weight         403.54

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'

_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                   14.3601(5)
_cell_length_b                   8.9695(3)
_cell_length_c                   15.4933(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.9420(10)
_cell_angle_gamma                90
_cell_volume                     1971.33(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9983
_cell_measurement_theta_min      5.72
_cell_measurement_theta_max      74.51

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.347
_exptl_crystal_size_mid          0.214
_exptl_crystal_size_min          0.176
_exptl_absorpt_coefficient_mu    2.554
_shelx_estimated_absorpt_T_min   0.471
_shelx_estimated_absorpt_T_max   0.662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.565842
_exptl_absorpt_correction_T_max  0.753817
_exptl_absorpt_process_details   'TWINABS v.2012/1'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            3495
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.115
_diffrn_reflns_theta_max         66.584
_diffrn_reflns_theta_full        66.584
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3495
_reflns_number_gt                3219
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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    'SHELXT-2015/1 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0275P)²+4.5661P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         3495
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1099
_refine_ls_wR_factor_gt          0.1062
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_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 0.17356(5) 0.19311(8) 0.49286(5) 0.01609(18) Uani 1 1 d . . . . .
O1 O 0.29493(14) 0.4501(2) 0.33704(13) 0.0140(4) Uani 1 1 d . . . . .
N1 N 0.38223(17) 0.2830(3) 0.42369(16) 0.0134(5) Uani 1 1 d . . . . .
C1 C 0.3450(2) 0.3676(3) 0.28422(19) 0.0125(6) Uani 1 1 d . . . . .
C2 C 0.3456(2) 0.3818(4) 0.1958(2) 0.0165(6) Uani 1 1 d . . . . .
H2 H 0.307926 0.453237 0.161027 0.020 Uiso 1 1 calc R U . . .
S2 S 0.08692(5) 0.46500(8) 0.41410(5) 0.01431(17) Uani 1 1 d . . . . .
C3 C 0.4050(2) 0.2848(4) 0.1610(2) 0.0195(7) Uani 1 1 d . . . . .
H3 H 0.408890 0.290361 0.100409 0.023 Uiso 1 1 calc R U . . .
C4 C 0.4596(2) 0.1788(4) 0.2127(2) 0.0216(7) Uani 1 1 d . . . . .
H4 H 0.499102 0.113909 0.186096 0.026 Uiso 1 1 calc R U . . .
C6 C 0.3988(2) 0.2641(3) 0.3376(2) 0.0134(6) Uani 1 1 d . . . . .
C5 C 0.4573(2) 0.1659(4) 0.3017(2) 0.0204(7) Uani 1 1 d . . . . .
H5 H 0.494092 0.093500 0.336506 0.024 Uiso 1 1 calc R U . . .
C7 C 0.32170(19) 0.3909(3) 0.41876(19) 0.0123(6) Uani 1 1 d . . . . .
C8 C 0.2800(2) 0.4576(3) 0.49238(19) 0.0129(6) Uani 1 1 d . . . . .
H8 H 0.321354 0.426678 0.547466 0.015 Uiso 1 1 calc R U . . .
C9 C 0.1800(2) 0.3960(3) 0.4978(2) 0.0136(6) Uani 1 1 d . . . . .
H9 H 0.163718 0.426876 0.555697 0.016 Uiso 1 1 calc R U . . .
C10 C 0.09837(19) 0.3189(3) 0.3408(2) 0.0128(6) Uani 1 1 d . . . . .
C11 C 0.0672(2) 0.3267(3) 0.25148(19) 0.0142(6) Uani 1 1 d . . . . .
H11 H 0.038590 0.415153 0.226046 0.017 Uiso 1 1 calc R U . . .
C12 C 0.0784(2) 0.2035(3) 0.1999(2) 0.0161(6) Uani 1 1 d . . . . .
H12 H 0.056799 0.207582 0.138780 0.019 Uiso 1 1 calc R U . . .
C13 C 0.1206(2) 0.0748(4) 0.2363(2) 0.0171(7) Uani 1 1 d . . . . .
H13 H 0.128017 -0.008372 0.200017 0.021 Uiso 1 1 calc R U . . .
C14 C 0.1525(2) 0.0664(3) 0.3260(2) 0.0170(6) Uani 1 1 d . . . . .
H14 H 0.181889 -0.021774 0.350970 0.020 Uiso 1 1 calc R U . . .
C15 C 0.1406(2) 0.1889(3) 0.37841(19) 0.0137(6) Uani 1 1 d . . . . .
C16 C 0.2830(2) 0.6304(3) 0.48959(19) 0.0127(6) Uani 1 1 d . . . . .
H16 H 0.241763 0.663898 0.435014 0.015 Uiso 1 1 calc R U . . .
C17 C 0.3835(2) 0.6870(4) 0.4863(2) 0.0163(6) Uani 1 1 d . . . . .
H17A H 0.425085 0.656079 0.540443 0.020 Uiso 1 1 calc R U . . .
H17B H 0.407434 0.639618 0.436382 0.020 Uiso 1 1 calc R U . . .
C18 C 0.3889(2) 0.8563(4) 0.4771(2) 0.0198(7) Uani 1 1 d . . . . .
H18A H 0.454587 0.886218 0.477519 0.030 Uiso 1 1 calc R U . . .
H18B H 0.364612 0.904126 0.525998 0.030 Uiso 1 1 calc R U . . .
H18C H 0.350862 0.887263 0.421962 0.030 Uiso 1 1 calc R U . . .
C19 C 0.2437(2) 0.6957(3) 0.56714(19) 0.0125(6) Uani 1 1 d . . . . .
C20 C 0.2934(2) 0.6826(3) 0.6520(2) 0.0159(6) Uani 1 1 d . . . . .
H20 H 0.351681 0.630603 0.661445 0.019 Uiso 1 1 calc R U . . .
C21 C 0.2585(2) 0.7445(4) 0.7224(2) 0.0187(7) Uani 1 1 d . . . . .
H21 H 0.293626 0.736387 0.779476 0.022 Uiso 1 1 calc R U . . .
C22 C 0.1723(2) 0.8186(3) 0.7099(2) 0.0193(7) Uani 1 1 d . . . . .
H22 H 0.147991 0.859908 0.758272 0.023 Uiso 1 1 calc R U . . .
C23 C 0.1222(2) 0.8315(3) 0.6261(2) 0.0203(7) Uani 1 1 d . . . . .
H23 H 0.063285 0.881803 0.616998 0.024 Uiso 1 1 calc R U . . .
C24 C 0.1579(2) 0.7712(3) 0.5554(2) 0.0157(6) Uani 1 1 d . . . . .
H24 H 0.123363 0.781556 0.498217 0.019 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 C15 1.763(3) . ?
S1 C9 1.823(3) . ?
O1 C7 1.372(3) . ?
O1 C1 1.385(3) . ?
N1 C7 1.295(4) . ?
N1 C6 1.402(4) . ?
C1 C2 1.378(4) . ?
C1 C6 1.394(4) . ?
C2 C3 1.384(5) . ?
C2 H2 0.9500 . ?
S2 C10 1.759(3) . ?
S2 C9 1.820(3) . ?
C3 C4 1.402(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(5) . ?
C4 H4 0.9500 . ?
C6 C5 1.391(4) . ?
C5 H5 0.9500 . ?
C7 C8 1.493(4) . ?
C8 C16 1.551(4) . ?
C8 C9 1.554(4) . ?
C8 H8 1.0000 . ?
C9 H9 1.0000 . ?
C10 C11 1.388(4) . ?
C10 C15 1.399(4) . ?
C11 C12 1.388(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.396(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(4) . ?
C14 H14 0.9500 . ?
C16 C19 1.522(4) . ?
C16 C17 1.539(4) . ?
C16 H16 1.0000 . ?
C17 C18 1.529(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C24 1.392(4) . ?
C19 C20 1.400(4) . ?
C20 C21 1.385(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.392(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.389(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.389(5) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?

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
C15 S1 C9 93.90(15) . . ?
C7 O1 C1 104.0(2) . . ?
C7 N1 C6 104.2(2) . . ?
C2 C1 O1 128.5(3) . . ?
C2 C1 C6 124.2(3) . . ?
O1 C1 C6 107.2(2) . . ?
C1 C2 C3 115.4(3) . . ?
C1 C2 H2 122.3 . . ?
C3 C2 H2 122.3 . . ?
C10 S2 C9 94.30(14) . . ?
C2 C3 C4 121.8(3) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 121.7(3) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C5 C6 C1 119.9(3) . . ?
C5 C6 N1 131.2(3) . . ?
C1 C6 N1 108.9(3) . . ?
C4 C5 C6 116.9(3) . . ?
C4 C5 H5 121.6 . . ?
C6 C5 H5 121.6 . . ?
N1 C7 O1 115.7(3) . . ?
N1 C7 C8 126.8(3) . . ?
O1 C7 C8 117.5(2) . . ?
C7 C8 C16 111.3(2) . . ?
C7 C8 C9 112.5(2) . . ?
C16 C8 C9 112.7(2) . . ?
C7 C8 H8 106.6 . . ?
C16 C8 H8 106.6 . . ?
C9 C8 H8 106.6 . . ?
C8 C9 S2 115.0(2) . . ?
C8 C9 S1 113.2(2) . . ?
S2 C9 S1 106.41(15) . . ?
C8 C9 H9 107.3 . . ?
S2 C9 H9 107.3 . . ?
S1 C9 H9 107.3 . . ?
C11 C10 C15 120.6(3) . . ?
C11 C10 S2 123.9(2) . . ?
C15 C10 S2 115.5(2) . . ?
C10 C11 C12 119.0(3) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C13 C12 C11 120.8(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 120.4(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 119.1(3) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C10 119.9(3) . . ?
C14 C15 S1 124.4(2) . . ?
C10 C15 S1 115.6(2) . . ?
C19 C16 C17 111.3(2) . . ?
C19 C16 C8 110.3(2) . . ?
C17 C16 C8 111.1(2) . . ?
C19 C16 H16 108.0 . . ?
C17 C16 H16 108.0 . . ?
C8 C16 H16 108.0 . . ?
C18 C17 C16 113.1(3) . . ?
C18 C17 H17A 109.0 . . ?
C16 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
C16 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C24 C19 C20 118.3(3) . . ?
C24 C19 C16 120.8(3) . . ?
C20 C19 C16 120.8(3) . . ?
C21 C20 C19 120.8(3) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 120.3(3) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C23 C22 C21 119.4(3) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 C24 120.3(3) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C19 120.9(3) . . ?
C23 C24 H24 119.5 . . ?
C19 C24 H24 119.5 . . ?

_refine_diff_density_max         0.340
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.070


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Pentane, DCM'
