# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2162103'
loop_
_audit_author_name
_audit_author_address
'Natalie Pridmore'
;University of Bristol
United Kingdom
;
_audit_update_record             
;
2022-03-25 deposited with the CCDC.	2022-05-20 downloaded from the CCDC.
;
_audit_creation_date             2019-05-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H15 P Se'
_chemical_formula_sum            'C18 H15 P Se'
_chemical_formula_weight         341.23
_chemical_melting_point          ?
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   16.6381(7)
_cell_length_b                   5.8673(3)
_cell_length_c                   16.6147(7)
_cell_angle_alpha                90
_cell_angle_beta                 107.392(3)
_cell_angle_gamma                90
_cell_volume                     1547.78(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4296
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.10
_cell_measurement_theta_min      2.51
_shelx_estimated_absorpt_T_max   0.766
_shelx_estimated_absorpt_T_min   0.421
_exptl_absorpt_coefficient_mu    2.516
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0753 before and 0.0529 after correction. The Ratio of minimum to maximum transmission is 0.7756. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             688
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.416
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.112
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            25128
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.013
_diffrn_reflns_theta_min         2.505
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3586
_reflns_number_total             4519
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         4519
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0308
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0270P)²+0.1402P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0624
_refine_ls_wR_factor_ref         0.0665
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
C1 C 0.63107(11) 0.6533(3) 0.19252(11) 0.0177(4) Uani 1 1 d . . . . .
C2 C 0.58452(12) 0.8376(3) 0.20642(13) 0.0229(4) Uani 1 1 d . . . . .
H2 H 0.6118 0.9601 0.2414 0.028 Uiso 1 1 calc R . . . .
C3 C 0.49794(13) 0.8420(3) 0.16898(14) 0.0278(4) Uani 1 1 d . . . . .
H3 H 0.4661 0.9685 0.1780 0.033 Uiso 1 1 calc R . . . .
C4 C 0.45786(13) 0.6637(3) 0.11867(13) 0.0269(4) Uani 1 1 d . . . . .
H4 H 0.3986 0.6676 0.0930 0.032 Uiso 1 1 calc R . . . .
C5 C 0.50463(12) 0.4783(4) 0.10567(12) 0.0256(4) Uani 1 1 d . . . . .
H5 H 0.4772 0.3544 0.0716 0.031 Uiso 1 1 calc R . . . .
C6 C 0.59121(12) 0.4743(3) 0.14238(12) 0.0221(4) Uani 1 1 d . . . . .
H6 H 0.6231 0.3483 0.1330 0.027 Uiso 1 1 calc R . . . .
C7 C 0.75761(11) 0.3764(3) 0.41035(11) 0.0156(4) Uani 1 1 d . . . . .
C8 C 0.71847(11) 0.5690(3) 0.43047(12) 0.0186(4) Uani 1 1 d . . . . .
H8 H 0.6998 0.6870 0.3900 0.022 Uiso 1 1 calc R . . . .
C9 C 0.70657(13) 0.5892(3) 0.50990(12) 0.0231(4) Uani 1 1 d . . . . .
H9 H 0.6799 0.7209 0.5233 0.028 Uiso 1 1 calc R . . . .
C10 C 0.73335(13) 0.4187(3) 0.56871(12) 0.0238(4) Uani 1 1 d . . . . .
H10 H 0.7253 0.4330 0.6227 0.029 Uiso 1 1 calc R . . . .
C11 C 0.77223(12) 0.2254(3) 0.54921(13) 0.0243(4) Uani 1 1 d . . . . .
H11 H 0.7908 0.1081 0.5900 0.029 Uiso 1 1 calc R . . . .
C12 C 0.78388(12) 0.2037(3) 0.47098(12) 0.0208(4) Uani 1 1 d . . . . .
H12 H 0.8100 0.0705 0.4579 0.025 Uiso 1 1 calc R . . . .
C13 C 0.88470(11) 0.3096(3) 0.33226(11) 0.0160(4) Uani 1 1 d . . . . .
C14 C 0.92253(12) 0.1278(3) 0.30341(12) 0.0211(4) Uani 1 1 d . . . . .
H14 H 0.8884 0.0128 0.2696 0.025 Uiso 1 1 calc R . . . .
C15 C 1.00980(13) 0.1132(3) 0.32372(14) 0.0255(4) Uani 1 1 d . . . . .
H15 H 1.0350 -0.0123 0.3043 0.031 Uiso 1 1 calc R . . . .
C16 C 1.05968(13) 0.2804(3) 0.37187(13) 0.0250(4) Uani 1 1 d . . . . .
H16 H 1.1193 0.2700 0.3858 0.030 Uiso 1 1 calc R . . . .
C17 C 1.02291(12) 0.4646(4) 0.40018(12) 0.0253(4) Uani 1 1 d . . . . .
H17 H 1.0574 0.5812 0.4325 0.030 Uiso 1 1 calc R . . . .
C18 C 0.93636(12) 0.4787(3) 0.38139(12) 0.0215(4) Uani 1 1 d . . . . .
H18 H 0.9117 0.6034 0.4018 0.026 Uiso 1 1 calc R . . . .
P1 P 0.76949(3) 0.31614(8) 0.30569(3) 0.01520(10) Uani 1 1 d . . . . .
Se1 Se 0.75191(2) 0.66094(3) 0.24189(2) 0.01861(6) Uani 1 1 d . . . . .


_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
C1 C2 1.389(2) . ?
C1 C6 1.381(3) . ?
C1 Se1 1.9316(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.380(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.392(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.394(2) . ?
C7 C12 1.403(2) . ?
C7 P1 1.8421(18) . ?
C8 H8 0.9500 . ?
C8 C9 1.397(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.376(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.391(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.376(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.394(2) . ?
C13 C18 1.404(2) . ?
C13 P1 1.8343(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.392(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.376(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.392(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.382(3) . ?
C18 H18 0.9500 . ?
P1 Se1 2.2620(5) . ?

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 C1 Se1 118.20(14) . . ?
C6 C1 C2 120.08(17) . . ?
C6 C1 Se1 121.69(14) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.68(18) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.42(18) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.68(19) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.04(18) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 120.08(18) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C8 C7 C12 118.74(17) . . ?
C8 C7 P1 124.86(14) . . ?
C12 C7 P1 116.16(13) . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.25(17) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.12(18) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.13(18) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.13(18) . . ?
C12 C11 H11 119.9 . . ?
C7 C12 H12 119.7 . . ?
C11 C12 C7 120.64(17) . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C18 118.67(17) . . ?
C14 C13 P1 118.69(14) . . ?
C18 C13 P1 122.63(14) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.61(18) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.09(18) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.03(18) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.25(18) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 H18 119.8 . . ?
C17 C18 C13 120.33(18) . . ?
C17 C18 H18 119.8 . . ?
C7 P1 Se1 103.62(6) . . ?
C13 P1 C7 100.15(8) . . ?
C13 P1 Se1 96.38(6) . . ?
C1 Se1 P1 98.66(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
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C6 C1 C2 C3 -0.6(3) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C8 C7 C12 C11 -0.8(3) . . . . ?
C8 C7 P1 C13 118.71(16) . . . . ?
C8 C7 P1 Se1 19.53(16) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
C10 C11 C12 C7 0.6(3) . . . . ?
C12 C7 C8 C9 0.6(3) . . . . ?
C12 C7 P1 C13 -67.05(15) . . . . ?
C12 C7 P1 Se1 -166.22(12) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
C14 C13 C18 C17 0.3(3) . . . . ?
C14 C13 P1 C7 131.62(15) . . . . ?
C14 C13 P1 Se1 -123.26(14) . . . . ?
C14 C15 C16 C17 -0.2(3) . . . . ?
C15 C16 C17 C18 1.2(3) . . . . ?
C16 C17 C18 C13 -1.2(3) . . . . ?
C18 C13 C14 C15 0.7(3) . . . . ?
C18 C13 P1 C7 -47.52(16) . . . . ?
C18 C13 P1 Se1 57.59(15) . . . . ?
P1 C7 C8 C9 174.66(14) . . . . ?
P1 C7 C12 C11 -175.44(15) . . . . ?
P1 C13 C14 C15 -178.50(15) . . . . ?
P1 C13 C18 C17 179.46(15) . . . . ?
Se1 C1 C2 C3 177.32(15) . . . . ?
Se1 C1 C6 C5 -177.81(14) . . . . ?

_olex2_exptl_crystal_mounting_method 'Oil on glass fibre'
_olex2_submission_special_instructions 'No special instructions were received'
