# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_BN0912
_database_code_depnum_ccdc_archive 'CCDC 2212955'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2022-10-14 deposited with the CCDC.	2022-12-05 downloaded from the CCDC.
;
_audit_creation_date             2022-10-14
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        N-phenylnaphtho[2,1-b]thiophen-1-amine
_chemical_formula_moiety         'C18 H13 N S'
_chemical_formula_sum            'C18 H13 N S'
_chemical_formula_weight         275.35
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H13 N S'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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                   5.7573(3)
_cell_length_b                   8.3305(6)
_cell_length_c                   30.537(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1464.58(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4542
_cell_measurement_temperature    293.1(10)
_cell_measurement_theta_max      23.4950
_cell_measurement_theta_min      3.5660
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.955
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  0.88192
_exptl_absorpt_correction_T_min  0.16952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.64a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_exptl_crystal_size_rad          0.400
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            14049
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_min         2.534
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.1(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  99.00   0.50   15.00    --   10.10  38.00  60.00  304
  2  ω    -53.00  99.00   0.50   15.00    --   10.10  38.00 -30.00  304
  3  ω    -48.00  90.00   0.50   15.00    --   10.10  38.00-150.00  276
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0264030000
_diffrn_orient_matrix_UB_12      0.0759996000
_diffrn_orient_matrix_UB_13      0.0091892000
_diffrn_orient_matrix_UB_21      0.0167739000
_diffrn_orient_matrix_UB_22      0.0363693000
_diffrn_orient_matrix_UB_23      -0.0207632000
_diffrn_orient_matrix_UB_31      -0.1191824000
_diffrn_orient_matrix_UB_32      -0.0117570000
_diffrn_orient_matrix_UB_33      -0.0049784000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.677
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1930
_reflns_number_total             2666
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 
;
 Flack x determined using 632 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2665
_refine_ls_number_restraints     126
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0463
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0575P)²+0.3018P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1207
_refine_ls_wR_factor_ref         0.1335
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 S1, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Uiso/Uaniso restraints and constraints
S1 \\sim C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8
\\sim C9 \\sim C10 \\sim C11 \\sim C12: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.01 within 2A
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14),
 C15(H15), C16(H16), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
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 0.5682(3) -0.08128(14) 0.35436(4) 0.1139(5) Uani 1 1 d . U . . .
N1 N 0.9060(6) 0.3335(4) 0.35417(11) 0.0787(9) Uani 1 1 d . . . . .
H1 H 1.010(11) 0.326(8) 0.3730(19) 0.16(2) Uiso 1 1 d . . . . .
C1 C 0.7450(7) 0.2043(5) 0.36054(12) 0.0724(9) Uani 1 1 d . U . . .
C2 C 0.7712(8) 0.0587(5) 0.33942(15) 0.0936(12) Uani 1 1 d . U . . .
H2 H 0.887805 0.038689 0.319065 0.112 Uiso 1 1 calc R U . . .
C3 C 0.4355(8) 0.0552(5) 0.38985(14) 0.0904(10) Uani 1 1 d . U . . .
C4 C 0.5468(7) 0.2058(4) 0.39005(11) 0.0706(8) Uani 1 1 d . U . . .
C5 C 0.4589(7) 0.3357(5) 0.41801(11) 0.0782(9) Uani 1 1 d . U . . .
C6 C 0.2572(8) 0.3007(7) 0.44442(14) 0.1040(13) Uani 1 1 d . U . . .
C7 C 0.1532(8) 0.1446(8) 0.44283(17) 0.1181(16) Uani 1 1 d . U . . .
H7 H 0.023645 0.124174 0.460143 0.142 Uiso 1 1 calc R U . . .
C8 C 0.2383(9) 0.0239(8) 0.41660(19) 0.1152(15) Uani 1 1 d . U . . .
H8 H 0.168015 -0.076584 0.416354 0.138 Uiso 1 1 calc R U . . .
C9 C 0.1634(10) 0.4303(9) 0.47139(17) 0.1336(18) Uani 1 1 d . U . . .
H9 H 0.034640 0.412324 0.489117 0.160 Uiso 1 1 calc R U . . .
C10 C 0.2670(12) 0.5789(9) 0.47034(19) 0.1388(19) Uani 1 1 d . U . . .
H10 H 0.202061 0.661580 0.486757 0.167 Uiso 1 1 calc R U . . .
C11 C 0.4620(12) 0.6102(7) 0.44610(15) 0.1208(16) Uani 1 1 d . U . . .
H11 H 0.529358 0.711644 0.447119 0.145 Uiso 1 1 calc R U . . .
C12 C 0.5591(9) 0.4924(5) 0.42018(13) 0.0913(11) Uani 1 1 d . U . . .
H12 H 0.691570 0.515199 0.403901 0.110 Uiso 1 1 calc R U . . .
C13 C 0.8772(6) 0.4573(4) 0.32347(11) 0.0621(9) Uani 1 1 d . . . . .
C14 C 0.6804(6) 0.4673(4) 0.29640(12) 0.0682(9) Uani 1 1 d . . . . .
H14 H 0.562361 0.391668 0.299067 0.082 Uiso 1 1 calc R U . . .
C15 C 0.6613(7) 0.5898(5) 0.26559(13) 0.0787(11) Uani 1 1 d . . . . .
H15 H 0.530526 0.595100 0.247755 0.094 Uiso 1 1 calc R U . . .
C16 C 0.8350(8) 0.7043(5) 0.26117(14) 0.0881(12) Uani 1 1 d . . . . .
H16 H 0.821988 0.784954 0.240270 0.106 Uiso 1 1 calc R U . . .
C17 C 1.0277(7) 0.6971(5) 0.28817(15) 0.0874(12) Uani 1 1 d . . . . .
H17 H 1.143616 0.774247 0.285636 0.105 Uiso 1 1 calc R U . . .
C18 C 1.0493(6) 0.5759(5) 0.31895(13) 0.0767(10) Uani 1 1 d . . . . .
H18 H 1.179734 0.572860 0.336902 0.092 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 C2 1.713(5) . ?
S1 C3 1.747(5) . ?
N1 H1 0.83(6) . ?
N1 C1 1.434(5) . ?
N1 C13 1.404(5) . ?
C1 C2 1.381(6) . ?
C1 C4 1.454(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.409(5) . ?
C3 C8 1.423(7) . ?
C4 C5 1.468(6) . ?
C5 C6 1.444(6) . ?
C5 C12 1.428(6) . ?
C6 C7 1.432(8) . ?
C6 C9 1.461(8) . ?
C7 H7 0.9300 . ?
C7 C8 1.376(8) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.375(8) . ?
C10 H10 0.9300 . ?
C10 C11 1.370(9) . ?
C11 H11 0.9300 . ?
C11 C12 1.380(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.405(5) . ?
C13 C18 1.406(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.393(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.388(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.385(5) . ?
C18 H18 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
C2 S1 C3 91.2(2) . . ?
C1 N1 H1 109(5) . . ?
C13 N1 H1 127(5) . . ?
C13 N1 C1 124.5(3) . . ?
N1 C1 C4 125.8(3) . . ?
C2 C1 N1 121.7(4) . . ?
C2 C1 C4 112.5(4) . . ?
S1 C2 H2 123.3 . . ?
C1 C2 S1 113.5(4) . . ?
C1 C2 H2 123.3 . . ?
C4 C3 S1 112.6(3) . . ?
C4 C3 C8 121.6(5) . . ?
C8 C3 S1 125.9(4) . . ?
C1 C4 C5 129.6(4) . . ?
C3 C4 C1 110.3(4) . . ?
C3 C4 C5 120.1(4) . . ?
C6 C5 C4 116.9(4) . . ?
C12 C5 C4 124.1(4) . . ?
C12 C5 C6 118.9(4) . . ?
C5 C6 C9 117.6(5) . . ?
C7 C6 C5 120.0(5) . . ?
C7 C6 C9 122.3(5) . . ?
C6 C7 H7 118.9 . . ?
C8 C7 C6 122.3(5) . . ?
C8 C7 H7 118.9 . . ?
C3 C8 H8 120.5 . . ?
C7 C8 C3 119.0(5) . . ?
C7 C8 H8 120.5 . . ?
C6 C9 H9 120.3 . . ?
C10 C9 C6 119.5(6) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 118.7 . . ?
C11 C10 C9 122.7(6) . . ?
C11 C10 H10 118.7 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.4(6) . . ?
C12 C11 H11 119.8 . . ?
C5 C12 H12 119.6 . . ?
C11 C12 C5 120.9(5) . . ?
C11 C12 H12 119.6 . . ?
N1 C13 C14 122.1(3) . . ?
N1 C13 C18 119.9(3) . . ?
C14 C13 C18 118.0(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.3(3) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.8(4) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.4(4) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.5(4) . . ?
C18 C17 H17 119.7 . . ?
C13 C18 H18 119.5 . . ?
C17 C18 C13 121.0(4) . . ?
C17 C18 H18 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
S1 C3 C4 C1 -0.6(4) . . . . ?
S1 C3 C4 C5 180.0(2) . . . . ?
S1 C3 C8 C7 -179.8(4) . . . . ?
N1 C1 C2 S1 176.5(3) . . . . ?
N1 C1 C4 C3 -176.4(3) . . . . ?
N1 C1 C4 C5 2.9(5) . . . . ?
N1 C13 C14 C15 -178.4(3) . . . . ?
N1 C13 C18 C17 178.4(4) . . . . ?
C1 N1 C13 C14 1.5(5) . . . . ?
C1 N1 C13 C18 -178.1(3) . . . . ?
C1 C4 C5 C6 -179.4(3) . . . . ?
C1 C4 C5 C12 1.1(6) . . . . ?
C2 S1 C3 C4 -0.1(3) . . . . ?
C2 S1 C3 C8 -179.5(4) . . . . ?
C2 C1 C4 C3 1.2(4) . . . . ?
C2 C1 C4 C5 -179.5(3) . . . . ?
C3 S1 C2 C1 0.7(4) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
C3 C4 C5 C12 -179.6(3) . . . . ?
C4 C1 C2 S1 -1.2(4) . . . . ?
C4 C3 C8 C7 0.8(7) . . . . ?
C4 C5 C6 C7 0.5(5) . . . . ?
C4 C5 C6 C9 -178.2(4) . . . . ?
C4 C5 C12 C11 177.7(4) . . . . ?
C5 C6 C7 C8 -0.2(7) . . . . ?
C5 C6 C9 C10 0.7(7) . . . . ?
C6 C5 C12 C11 -1.8(6) . . . . ?
C6 C7 C8 C3 -0.4(8) . . . . ?
C6 C9 C10 C11 -2.5(9) . . . . ?
C7 C6 C9 C10 -177.9(5) . . . . ?
C8 C3 C4 C1 178.9(4) . . . . ?
C8 C3 C4 C5 -0.5(6) . . . . ?
C9 C6 C7 C8 178.4(4) . . . . ?
C9 C10 C11 C12 2.2(8) . . . . ?
C10 C11 C12 C5 0.1(7) . . . . ?
C12 C5 C6 C7 180.0(4) . . . . ?
C12 C5 C6 C9 1.3(5) . . . . ?
C13 N1 C1 C2 94.0(5) . . . . ?
C13 N1 C1 C4 -88.6(5) . . . . ?
C13 C14 C15 C16 -0.2(6) . . . . ?
C14 C13 C18 C17 -1.2(5) . . . . ?
C14 C15 C16 C17 -0.8(6) . . . . ?
C15 C16 C17 C18 0.9(6) . . . . ?
C16 C17 C18 C13 0.2(6) . . . . ?
C18 C13 C14 C15 1.2(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.778
_oxdiff_exptl_absorpt_empirical_full_min 0.578

