# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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 1831422'
_audit_update_record             
;
2018-04-23 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;
_audit_creation_date             2018-04-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H17 N O'
_chemical_formula_sum            'C24 H17 N O'
_chemical_formula_weight         335.38
_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 0.0181 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'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   16.0364(4)
_cell_length_b                   7.5753(2)
_cell_length_c                   16.7540(4)
_cell_angle_alpha                90
_cell_angle_beta                 117.2140(10)
_cell_angle_gamma                90
_cell_volume                     1809.99(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4383
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      63.68
_cell_measurement_theta_min      3.10
_shelx_estimated_absorpt_T_max   0.882
_shelx_estimated_absorpt_T_min   0.853
_exptl_absorpt_coefficient_mu    0.585
_exptl_absorpt_correction_T_max  0.879
_exptl_absorpt_correction_T_min  0.849
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.244
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7314
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        63.785
_diffrn_reflns_theta_max         63.785
_diffrn_reflns_theta_min         3.161
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_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                2663
_reflns_number_total             2941
_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 v8.27A (Bruker, 2012)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_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    ?
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2941
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0509
_refine_ls_restrained_S_all      1.087
_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)+(0.0951P)²+0.1923P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1370
_refine_ls_wR_factor_ref         0.1523
_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:
 C6(H6), C12(H12), C11(H11), C15(H15), C9(H9), C8(H8), C23(H23), C22(H22),
 C5(H5), C14(H14), C16(H16), C1(H1), C21(H21), C20(H20), C17(H17), C3(H3),
 C2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C6 C 0.69913(17) 0.9354(3) -0.15751(14) 0.0956(6) Uani 1 1 d . . . . .
H6 H 0.6366 0.9300 -0.1692 0.115 Uiso 1 1 calc R . . . .
O1 O 0.93045(9) 0.76843(17) 0.00132(10) 0.0919(5) Uani 1 1 d . . . . .
C12 C 0.88101(12) 0.4662(2) -0.00957(11) 0.0686(4) Uani 1 1 d . . . . .
H12 H 0.8692 0.4625 -0.0693 0.082 Uiso 1 1 calc R . . . .
C11 C 0.86880(11) 0.3172(2) 0.03118(10) 0.0609(4) Uani 1 1 d . . . . .
H11 H 0.8498 0.2120 -0.0007 0.073 Uiso 1 1 calc R . . . .
C15 C 0.63129(14) -0.0094(3) 0.04877(14) 0.0883(6) Uani 1 1 d . . . . .
H15 H 0.5732 0.0037 -0.0011 0.106 Uiso 1 1 calc R . . . .
C9 C 0.91433(13) 0.4805(2) 0.16687(11) 0.0714(4) Uani 1 1 d . . . . .
H9 H 0.9249 0.4856 0.2262 0.086 Uiso 1 1 calc R . . . .
C8 C 0.92815(13) 0.6287(2) 0.12661(13) 0.0745(5) Uani 1 1 d . . . . .
H8 H 0.9490 0.7332 0.1588 0.089 Uiso 1 1 calc R . . . .
C23 C 1.03229(13) 0.1440(3) 0.29271(12) 0.0782(5) Uani 1 1 d . . . . .
H23 H 1.0589 0.2363 0.2756 0.094 Uiso 1 1 calc R . . . .
C22 C 1.08447(17) 0.0478(3) 0.36904(14) 0.0986(7) Uani 1 1 d . . . . .
H22 H 1.1475 0.0748 0.4039 0.118 Uiso 1 1 calc R . . . .
C5 C 0.76677(13) 0.8410(2) -0.08632(12) 0.0761(5) Uani 1 1 d . . . . .
H5 H 0.7500 0.7721 -0.0500 0.091 Uiso 1 1 calc R . . . .
C7 C 0.91076(11) 0.6205(2) 0.03862(11) 0.0657(4) Uani 1 1 d . . . . .
N1 N 0.87204(9) 0.17168(16) 0.16177(8) 0.0617(4) Uani 1 1 d . . . . .
C13 C 0.78886(11) 0.0781(2) 0.13440(10) 0.0593(4) Uani 1 1 d . . . . .
C14 C 0.70349(12) 0.1029(2) 0.05995(12) 0.0726(5) Uani 1 1 d . . . . .
H14 H 0.6949 0.1922 0.0188 0.087 Uiso 1 1 calc R . . . .
C16 C 0.64353(17) -0.1417(3) 0.11044(17) 0.0977(7) Uani 1 1 d . . . . .
H16 H 0.5935 -0.2152 0.1014 0.117 Uiso 1 1 calc R . . . .
C24 C 0.93910(11) 0.0994(2) 0.24224(10) 0.0625(4) Uani 1 1 d . . . . .
C18 C 0.80236(13) -0.0549(2) 0.19749(11) 0.0666(4) Uani 1 1 d . . . . .
C1 C 0.7247(2) 1.0366(3) -0.21049(15) 0.1128(9) Uani 1 1 d . . . . .
H1 H 0.6795 1.0989 -0.2587 0.135 Uiso 1 1 calc R . . . .
C4 C 0.85840(13) 0.85045(19) -0.07020(11) 0.0673(4) Uani 1 1 d . . . . .
C10 C 0.88484(10) 0.32455(18) 0.11934(10) 0.0558(4) Uani 1 1 d . . . . .
C21 C 1.0445(2) -0.0894(4) 0.39502(16) 0.1117(8) Uani 1 1 d . . . . .
H21 H 1.0810 -0.1514 0.4475 0.134 Uiso 1 1 calc R . . . .
C20 C 0.95248(19) -0.1346(3) 0.34473(14) 0.0956(7) Uani 1 1 d . . . . .
H20 H 0.9266 -0.2269 0.3626 0.115 Uiso 1 1 calc R . . . .
C19 C 0.89801(13) -0.0414(2) 0.26652(11) 0.0684(4) Uani 1 1 d . . . . .
C17 C 0.72778(17) -0.1656(3) 0.18405(16) 0.0873(6) Uani 1 1 d . . . . .
H17 H 0.7354 -0.2549 0.2249 0.105 Uiso 1 1 calc R . . . .
C3 C 0.88443(17) 0.9530(2) -0.12273(13) 0.0844(6) Uani 1 1 d . . . . .
H3 H 0.9469 0.9589 -0.1111 0.101 Uiso 1 1 calc R . . . .
C2 C 0.8175(3) 1.0460(3) -0.19227(17) 0.1126(9) Uani 1 1 d . . . . .
H2 H 0.8347 1.1166 -0.2277 0.135 Uiso 1 1 calc R . . . .


_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
C6 H6 0.9300 . ?
C6 C5 1.388(3) . ?
C6 C1 1.370(3) . ?
O1 C7 1.3882(18) . ?
O1 C4 1.375(2) . ?
C12 H12 0.9300 . ?
C12 C11 1.379(2) . ?
C12 C7 1.376(2) . ?
C11 H11 0.9300 . ?
C11 C10 1.380(2) . ?
C15 H15 0.9300 . ?
C15 C14 1.379(3) . ?
C15 C16 1.387(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.379(2) . ?
C9 C10 1.382(2) . ?
C8 H8 0.9300 . ?
C8 C7 1.371(2) . ?
C23 H23 0.9300 . ?
C23 C22 1.374(3) . ?
C23 C24 1.381(2) . ?
C22 H22 0.9300 . ?
C22 C21 1.392(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.369(3) . ?
N1 C13 1.3902(19) . ?
N1 C24 1.396(2) . ?
N1 C10 1.4220(18) . ?
C13 C14 1.380(2) . ?
C13 C18 1.404(2) . ?
C14 H14 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.362(3) . ?
C24 C19 1.408(2) . ?
C18 C19 1.442(3) . ?
C18 C17 1.392(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.376(4) . ?
C4 C3 1.374(2) . ?
C21 H21 0.9300 . ?
C21 C20 1.366(4) . ?
C20 H20 0.9300 . ?
C20 C19 1.390(3) . ?
C17 H17 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.365(3) . ?
C2 H2 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
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C1 C6 C5 119.8(2) . . ?
C4 O1 C7 118.93(13) . . ?
C11 C12 H12 120.2 . . ?
C7 C12 H12 120.2 . . ?
C7 C12 C11 119.64(15) . . ?
C12 C11 H11 120.1 . . ?
C12 C11 C10 119.87(14) . . ?
C10 C11 H11 120.1 . . ?
C14 C15 H15 119.3 . . ?
C14 C15 C16 121.4(2) . . ?
C16 C15 H15 119.3 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.23(15) . . ?
C10 C9 H9 119.9 . . ?
C9 C8 H8 120.3 . . ?
C7 C8 C9 119.32(15) . . ?
C7 C8 H8 120.3 . . ?
C22 C23 H23 121.0 . . ?
C22 C23 C24 117.91(19) . . ?
C24 C23 H23 121.0 . . ?
C23 C22 H22 119.5 . . ?
C23 C22 C21 121.0(2) . . ?
C21 C22 H22 119.5 . . ?
C6 C5 H5 120.4 . . ?
C4 C5 C6 119.26(19) . . ?
C4 C5 H5 120.4 . . ?
C12 C7 O1 120.73(16) . . ?
C8 C7 O1 118.09(15) . . ?
C8 C7 C12 121.02(14) . . ?
C13 N1 C24 108.53(12) . . ?
C13 N1 C10 125.91(12) . . ?
C24 N1 C10 125.37(12) . . ?
N1 C13 C18 108.87(14) . . ?
C14 C13 N1 129.38(14) . . ?
C14 C13 C18 121.75(15) . . ?
C15 C14 C13 117.58(18) . . ?
C15 C14 H14 121.2 . . ?
C13 C14 H14 121.2 . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 120.93(18) . . ?
C17 C16 H16 119.5 . . ?
C23 C24 N1 129.47(15) . . ?
C23 C24 C19 121.79(15) . . ?
N1 C24 C19 108.70(14) . . ?
C13 C18 C19 107.10(13) . . ?
C17 C18 C13 119.03(18) . . ?
C17 C18 C19 133.86(17) . . ?
C6 C1 H1 120.1 . . ?
C6 C1 C2 119.9(2) . . ?
C2 C1 H1 120.0 . . ?
C5 C4 O1 123.13(15) . . ?
C5 C4 C3 121.09(17) . . ?
C3 C4 O1 115.67(17) . . ?
C11 C10 C9 119.90(14) . . ?
C11 C10 N1 120.24(13) . . ?
C9 C10 N1 119.86(13) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 C22 121.1(2) . . ?
C20 C21 H21 119.5 . . ?
C21 C20 H20 120.3 . . ?
C21 C20 C19 119.3(2) . . ?
C19 C20 H20 120.3 . . ?
C24 C19 C18 106.79(13) . . ?
C20 C19 C24 118.81(18) . . ?
C20 C19 C18 134.39(17) . . ?
C16 C17 C18 119.34(19) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C4 C3 H3 120.4 . . ?
C2 C3 C4 119.2(2) . . ?
C2 C3 H3 120.4 . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2 119.6 . . ?

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
C6 C5 C4 O1 176.70(17) . . . . ?
C6 C5 C4 C3 0.6(3) . . . . ?
C6 C1 C2 C3 1.2(4) . . . . ?
O1 C4 C3 C2 -176.63(18) . . . . ?
C12 C11 C10 C9 -0.9(2) . . . . ?
C12 C11 C10 N1 179.74(14) . . . . ?
C11 C12 C7 O1 175.06(14) . . . . ?
C11 C12 C7 C8 -0.3(3) . . . . ?
C15 C16 C17 C18 0.2(3) . . . . ?
C9 C8 C7 O1 -176.31(15) . . . . ?
C9 C8 C7 C12 -0.9(3) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C8 C9 C10 N1 179.12(15) . . . . ?
C23 C22 C21 C20 1.1(4) . . . . ?
C23 C24 C19 C18 -177.52(15) . . . . ?
C23 C24 C19 C20 1.7(2) . . . . ?
C22 C23 C24 N1 -178.21(17) . . . . ?
C22 C23 C24 C19 -0.9(3) . . . . ?
C22 C21 C20 C19 -0.2(4) . . . . ?
C5 C6 C1 C2 -0.8(4) . . . . ?
C5 C4 C3 C2 -0.3(3) . . . . ?
C7 O1 C4 C5 25.3(2) . . . . ?
C7 O1 C4 C3 -158.39(16) . . . . ?
C7 C12 C11 C10 1.2(2) . . . . ?
N1 C13 C14 C15 -179.64(15) . . . . ?
N1 C13 C18 C19 0.16(17) . . . . ?
N1 C13 C18 C17 179.71(14) . . . . ?
N1 C24 C19 C18 0.30(17) . . . . ?
N1 C24 C19 C20 179.50(15) . . . . ?
C13 N1 C24 C23 177.39(17) . . . . ?
C13 N1 C24 C19 -0.21(17) . . . . ?
C13 N1 C10 C11 -60.0(2) . . . . ?
C13 N1 C10 C9 120.64(17) . . . . ?
C13 C18 C19 C24 -0.29(17) . . . . ?
C13 C18 C19 C20 -179.30(19) . . . . ?
C13 C18 C17 C16 -0.3(3) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C14 C13 C18 C19 -178.97(14) . . . . ?
C14 C13 C18 C17 0.6(2) . . . . ?
C16 C15 C14 C13 0.6(3) . . . . ?
C24 C23 C22 C21 -0.5(3) . . . . ?
C24 N1 C13 C14 179.07(15) . . . . ?
C24 N1 C13 C18 0.02(17) . . . . ?
C24 N1 C10 C11 125.69(16) . . . . ?
C24 N1 C10 C9 -53.7(2) . . . . ?
C18 C13 C14 C15 -0.7(2) . . . . ?
C1 C6 C5 C4 -0.1(3) . . . . ?
C4 O1 C7 C12 66.3(2) . . . . ?
C4 O1 C7 C8 -118.24(19) . . . . ?
C4 C3 C2 C1 -0.6(3) . . . . ?
C10 C9 C8 C7 1.1(3) . . . . ?
C10 N1 C13 C14 4.0(3) . . . . ?
C10 N1 C13 C18 -175.09(13) . . . . ?
C10 N1 C24 C23 -7.5(3) . . . . ?
C10 N1 C24 C19 174.94(13) . . . . ?
C21 C20 C19 C24 -1.1(3) . . . . ?
C21 C20 C19 C18 177.8(2) . . . . ?
C19 C18 C17 C16 179.08(18) . . . . ?
C17 C18 C19 C24 -179.74(18) . . . . ?
C17 C18 C19 C20 1.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1831423'
_audit_update_record             
;
2018-04-23 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;
_audit_creation_date             2018-04-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H17 N S'
_chemical_formula_sum            'C24 H17 N S'
_chemical_formula_weight         351.44
_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'
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      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                   14.7755(6)
_cell_length_b                   16.6199(6)
_cell_length_c                   7.5149(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.0350(10)
_cell_angle_gamma                90
_cell_volume                     1817.18(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9605
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.82
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.950
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1475 before and 0.0711 after correction.
The Ratio of minimum to maximum transmission is 0.9557.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.246
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            62652
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.519
_diffrn_reflns_theta_min         2.451
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3617
_reflns_number_total             4171
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    ?
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.569
_refine_diff_density_rms         0.204
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4171
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.156
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0548P)²+0.6411P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1122
_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:
 C1(H1), C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C14(H14),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
N1 N 0.70138(8) 0.91108(7) 1.02256(15) 0.0212(2) Uani 1 1 d . . . . .
S1 S 0.65337(3) 1.11912(2) 0.36524(5) 0.02911(12) Uani 1 1 d . . . . .
C1 C 0.83465(10) 1.07470(9) 0.35093(19) 0.0254(3) Uani 1 1 d . . . . .
H1 H 0.8277 1.0306 0.4279 0.031 Uiso 1 1 calc R . . . .
C2 C 0.76202(10) 1.12778(8) 0.29818(18) 0.0223(3) Uani 1 1 d . . . . .
C3 C 0.77235(11) 1.19144(9) 0.18116(19) 0.0263(3) Uani 1 1 d . . . . .
H3 H 0.7228 1.2274 0.1433 0.032 Uiso 1 1 calc R . . . .
C4 C 0.73702(10) 1.07618(8) 0.71166(19) 0.0232(3) Uani 1 1 d . . . . .
H4 H 0.7730 1.1236 0.7121 0.028 Uiso 1 1 calc R . . . .
C5 C 0.67460(9) 1.05507(9) 0.55678(18) 0.0220(3) Uani 1 1 d . . . . .
C6 C 0.62324(10) 0.98497(9) 0.55571(18) 0.0230(3) Uani 1 1 d . . . . .
H6 H 0.5816 0.9700 0.4499 0.028 Uiso 1 1 calc R . . . .
C7 C 0.63255(10) 0.93673(8) 0.70897(18) 0.0221(3) Uani 1 1 d . . . . .
H7 H 0.5973 0.8889 0.7079 0.027 Uiso 1 1 calc R . . . .
C8 C 0.69369(9) 0.95871(8) 0.86416(18) 0.0199(3) Uani 1 1 d . . . . .
C9 C 0.85479(11) 1.20188(10) 0.1207(2) 0.0314(4) Uani 1 1 d . . . . .
H9 H 0.8614 1.2448 0.0406 0.038 Uiso 1 1 calc R . . . .
C10 C 0.92784(12) 1.15008(11) 0.1762(2) 0.0338(4) Uani 1 1 d . . . . .
H10 H 0.9848 1.1580 0.1364 0.041 Uiso 1 1 calc R . . . .
C11 C 0.91710(11) 1.08640(10) 0.2907(2) 0.0307(3) Uani 1 1 d . . . . .
H11 H 0.9668 1.0505 0.3279 0.037 Uiso 1 1 calc R . . . .
C13 C 0.78329(10) 0.88483(8) 1.12911(19) 0.0230(3) Uani 1 1 d . . . . .
C14 C 0.87354(11) 0.89537(9) 1.1041(2) 0.0290(3) Uani 1 1 d . . . . .
H14 H 0.8877 0.9245 1.0037 0.035 Uiso 1 1 calc R . . . .
C15 C 0.76146(11) 0.83951(8) 1.27492(19) 0.0246(3) Uani 1 1 d . . . . .
C16 C 0.62774(10) 0.88276(8) 1.09944(18) 0.0208(3) Uani 1 1 d . . . . .
C17 C 0.53379(10) 0.89454(8) 1.0446(2) 0.0244(3) Uani 1 1 d . . . . .
H17 H 0.5106 0.9265 0.9420 0.029 Uiso 1 1 calc R . . . .
C18 C 0.74663(9) 1.02822(8) 0.86435(18) 0.0217(3) Uani 1 1 d . . . . .
H18 H 0.7893 1.0426 0.9693 0.026 Uiso 1 1 calc R . . . .
C19 C 0.47521(11) 0.85789(9) 1.1454(2) 0.0306(3) Uani 1 1 d . . . . .
H19 H 0.4107 0.8649 1.1106 0.037 Uiso 1 1 calc R . . . .
C20 C 0.50854(12) 0.81077(9) 1.2970(2) 0.0337(4) Uani 1 1 d . . . . .
H20 H 0.4666 0.7856 1.3620 0.040 Uiso 1 1 calc R . . . .
C21 C 0.60175(12) 0.80056(9) 1.3530(2) 0.0295(3) Uani 1 1 d . . . . .
H21 H 0.6243 0.7691 1.4568 0.035 Uiso 1 1 calc R . . . .
C22 C 0.66267(10) 0.83721(8) 1.25480(18) 0.0231(3) Uani 1 1 d . . . . .
C23 C 0.83237(12) 0.80662(9) 1.4022(2) 0.0322(4) Uani 1 1 d . . . . .
H23 H 0.8189 0.7768 1.5022 0.039 Uiso 1 1 calc R . . . .
C24 C 0.92194(12) 0.81838(10) 1.3797(2) 0.0372(4) Uani 1 1 d . . . . .
H24 H 0.9706 0.7968 1.4658 0.045 Uiso 1 1 calc R . . . .
C25 C 0.94230(12) 0.86157(10) 1.2321(2) 0.0357(4) Uani 1 1 d . . . . .
H25 H 1.0047 0.8680 1.2188 0.043 Uiso 1 1 calc R . . . .


_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
N1 C8 1.4176(17) . ?
N1 C13 1.3995(18) . ?
N1 C16 1.3993(18) . ?
S1 C2 1.7702(15) . ?
S1 C5 1.7737(14) . ?
C1 C2 1.392(2) . ?
C1 C11 1.385(2) . ?
C2 C3 1.401(2) . ?
C3 C9 1.383(2) . ?
C4 C5 1.398(2) . ?
C4 C18 1.3840(19) . ?
C5 C6 1.390(2) . ?
C6 C7 1.390(2) . ?
C7 C8 1.3937(19) . ?
C8 C18 1.395(2) . ?
C9 C10 1.387(2) . ?
C10 C11 1.390(2) . ?
C13 C14 1.390(2) . ?
C13 C15 1.413(2) . ?
C14 C25 1.390(2) . ?
C15 C22 1.442(2) . ?
C15 C23 1.401(2) . ?
C16 C17 1.391(2) . ?
C16 C22 1.4116(19) . ?
C17 C19 1.386(2) . ?
C19 C20 1.400(2) . ?
C20 C21 1.379(2) . ?
C21 C22 1.399(2) . ?
C23 C24 1.377(3) . ?
C24 C25 1.397(3) . ?

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
C13 N1 C8 126.10(12) . . ?
C16 N1 C8 125.46(11) . . ?
C16 N1 C13 108.43(11) . . ?
C2 S1 C5 103.82(7) . . ?
C11 C1 C2 119.73(14) . . ?
C1 C2 S1 124.03(11) . . ?
C1 C2 C3 119.62(14) . . ?
C3 C2 S1 116.33(11) . . ?
C9 C3 C2 119.96(14) . . ?
C18 C4 C5 120.21(13) . . ?
C4 C5 S1 121.52(11) . . ?
C6 C5 S1 118.64(11) . . ?
C6 C5 C4 119.71(12) . . ?
C5 C6 C7 120.23(13) . . ?
C6 C7 C8 119.88(13) . . ?
C7 C8 N1 120.12(12) . . ?
C7 C8 C18 119.97(12) . . ?
C18 C8 N1 119.91(12) . . ?
C3 C9 C10 120.47(14) . . ?
C9 C10 C11 119.47(15) . . ?
C1 C11 C10 120.72(15) . . ?
N1 C13 C15 108.56(13) . . ?
C14 C13 N1 129.65(14) . . ?
C14 C13 C15 121.74(13) . . ?
C13 C14 C25 117.30(15) . . ?
C13 C15 C22 107.26(12) . . ?
C23 C15 C13 119.54(15) . . ?
C23 C15 C22 133.20(14) . . ?
N1 C16 C22 108.86(12) . . ?
C17 C16 N1 129.64(13) . . ?
C17 C16 C22 121.50(13) . . ?
C19 C17 C16 117.53(14) . . ?
C4 C18 C8 119.98(13) . . ?
C17 C19 C20 121.73(15) . . ?
C21 C20 C19 120.54(14) . . ?
C20 C21 C22 119.08(14) . . ?
C16 C22 C15 106.87(12) . . ?
C21 C22 C15 133.55(14) . . ?
C21 C22 C16 119.58(14) . . ?
C24 C23 C15 118.76(15) . . ?
C23 C24 C25 120.99(15) . . ?
C14 C25 C24 121.62(16) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1831424'
_audit_update_record             
;
2018-03-21 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H17 N Se'
_chemical_formula_weight         398.34

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'
Se Se -0.0929 2.2259 '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                   14.9778(5)
_cell_length_b                   16.6273(6)
_cell_length_c                   7.5305(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.6790(10)
_cell_angle_gamma                90
_cell_volume                     1848.70(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    9815
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      27.49

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    2.037
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            60339
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.450
_diffrn_reflns_theta_max         27.556
_diffrn_reflns_theta_full        25.242
_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             4254
_reflns_number_gt                3819
_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    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0392P)²+0.7130P] 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         4254
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0259
_refine_ls_wR_factor_ref         0.0729
_refine_ls_wR_factor_gt          0.0703
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_refine_ls_shift/su_max          0.004
_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
N1 N 0.70237(9) 0.91130(8) 0.53057(17) 0.0204(3) Uani 1 1 d . . . . .
Se1 Se 0.64710(2) 1.12223(2) -0.14270(2) 0.02794(7) Uani 1 1 d . . . . .
C1 C 0.63351(11) 0.93545(9) 0.2189(2) 0.0214(3) Uani 1 1 d . . . . .
H1 H 0.5996 0.8872 0.2200 0.026 Uiso 1 1 calc R U . . .
C2 C 0.62271(10) 0.98324(9) 0.0650(2) 0.0212(3) Uani 1 1 d . . . . .
H2 H 0.5813 0.9677 -0.0391 0.025 Uiso 1 1 calc R U . . .
C3 C 0.67238(11) 1.05358(9) 0.0637(2) 0.0215(3) Uani 1 1 d . . . . .
C4 C 0.73463(11) 1.07552(10) 0.2152(2) 0.0228(3) Uani 1 1 d . . . . .
H4 H 0.7696 1.1231 0.2132 0.027 Uiso 1 1 calc R U . . .
C5 C 0.76453(12) 1.13056(9) -0.2098(2) 0.0222(3) Uani 1 1 d . . . . .
C6 C 0.83501(12) 1.07726(10) -0.1507(2) 0.0250(3) Uani 1 1 d . . . . .
H6 H 0.8265 1.0341 -0.0726 0.030 Uiso 1 1 calc R U . . .
C7 C 0.91765(12) 1.08764(11) -0.2070(2) 0.0311(4) Uani 1 1 d . . . . .
H7 H 0.9661 1.0518 -0.1656 0.037 Uiso 1 1 calc R U . . .
C8 C 0.74543(11) 1.02800(9) 0.3685(2) 0.0212(3) Uani 1 1 d . . . . .
H8 H 0.7878 1.0429 0.4717 0.025 Uiso 1 1 calc R U . . .
C9 C 0.69414(10) 0.95847(9) 0.37127(19) 0.0191(3) Uani 1 1 d . . . . .
C11 C 0.63035(11) 0.88278(8) 0.6086(2) 0.0198(3) Uani 1 1 d . . . . .
C12 C 0.66541(12) 0.83699(9) 0.7626(2) 0.0224(3) Uani 1 1 d . . . . .
C13 C 0.76246(12) 0.83933(9) 0.7804(2) 0.0245(3) Uani 1 1 d . . . . .
C14 C 0.78353(12) 0.88506(9) 0.6343(2) 0.0229(3) Uani 1 1 d . . . . .
C15 C 0.87229(12) 0.89579(11) 0.6076(2) 0.0289(4) Uani 1 1 d . . . . .
H15 H 0.8859 0.9253 0.5074 0.035 Uiso 1 1 calc R U . . .
C16 C 0.94029(14) 0.86171(12) 0.7330(3) 0.0365(4) Uani 1 1 d . . . . .
H16 H 1.0016 0.8681 0.7181 0.044 Uiso 1 1 calc R U . . .
C17 C 0.92082(14) 0.81837(12) 0.8804(3) 0.0383(4) Uani 1 1 d . . . . .
H17 H 0.9690 0.7968 0.9651 0.046 Uiso 1 1 calc R U . . .
C18 C 0.83283(13) 0.80643(10) 0.9050(2) 0.0325(4) Uani 1 1 d . . . . .
H18 H 0.8200 0.7763 1.0050 0.039 Uiso 1 1 calc R U . . .
C19 C 0.60556(13) 0.79977(9) 0.8611(2) 0.0287(4) Uani 1 1 d . . . . .
H19 H 0.6280 0.7679 0.9636 0.034 Uiso 1 1 calc R U . . .
C20 C 0.48023(13) 0.85745(10) 0.6579(2) 0.0295(4) Uani 1 1 d . . . . .
H20 H 0.4166 0.8645 0.6249 0.035 Uiso 1 1 calc R U . . .
C21 C 0.53786(12) 0.89472(9) 0.5564(2) 0.0235(3) Uani 1 1 d . . . . .
H21 H 0.5148 0.9271 0.4552 0.028 Uiso 1 1 calc R U . . .
C22 C 0.51382(14) 0.80992(10) 0.8074(2) 0.0328(4) Uani 1 1 d . . . . .
H22 H 0.4728 0.7843 0.8728 0.039 Uiso 1 1 calc R U . . .
C23 C 0.77672(12) 1.19273(10) -0.3279(2) 0.0264(3) Uani 1 1 d . . . . .
H23 H 0.7284 1.2287 -0.3694 0.032 Uiso 1 1 calc R U . . .
C24 C 0.85953(13) 1.20181(11) -0.3844(2) 0.0329(4) Uani 1 1 d . . . . .
H24 H 0.8677 1.2439 -0.4655 0.039 Uiso 1 1 calc R U . . .
C25 C 0.93040(13) 1.14997(12) -0.3233(2) 0.0345(4) Uani 1 1 d . . . . .
H25 H 0.9874 1.1569 -0.3607 0.041 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
N1 C11 1.395(2) . ?
N1 C14 1.399(2) . ?
N1 C9 1.4211(19) . ?
Se1 C3 1.9143(15) . ?
Se1 C5 1.9149(17) . ?
C1 C9 1.392(2) . ?
C1 C2 1.392(2) . ?
C2 C3 1.387(2) . ?
C3 C4 1.395(2) . ?
C4 C8 1.386(2) . ?
C5 C6 1.393(2) . ?
C5 C23 1.396(2) . ?
C6 C7 1.385(3) . ?
C7 C25 1.391(3) . ?
C8 C9 1.390(2) . ?
C11 C21 1.389(2) . ?
C11 C12 1.413(2) . ?
C12 C19 1.400(2) . ?
C12 C13 1.438(2) . ?
C13 C18 1.399(2) . ?
C13 C14 1.416(2) . ?
C14 C15 1.389(3) . ?
C15 C16 1.388(3) . ?
C16 C17 1.395(3) . ?
C17 C18 1.376(3) . ?
C19 C22 1.376(3) . ?
C20 C21 1.391(2) . ?
C20 C22 1.398(3) . ?
C23 C24 1.385(3) . ?
C24 C25 1.385(3) . ?

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
C11 N1 C14 108.63(13) . . ?
C11 N1 C9 125.42(13) . . ?
C14 N1 C9 125.94(13) . . ?
C3 Se1 C5 101.09(7) . . ?
C9 C1 C2 119.84(14) . . ?
C3 C2 C1 120.00(14) . . ?
C2 C3 C4 120.01(14) . . ?
C2 C3 Se1 118.39(11) . . ?
C4 C3 Se1 121.46(12) . . ?
C8 C4 C3 120.04(15) . . ?
C6 C5 C23 120.10(16) . . ?
C6 C5 Se1 123.38(12) . . ?
C23 C5 Se1 116.50(13) . . ?
C7 C6 C5 119.44(15) . . ?
C6 C7 C25 120.66(17) . . ?
C4 C8 C9 119.94(14) . . ?
C8 C9 C1 120.14(14) . . ?
C8 C9 N1 120.12(13) . . ?
C1 C9 N1 119.74(14) . . ?
C21 C11 N1 129.57(14) . . ?
C21 C11 C12 121.65(15) . . ?
N1 C11 C12 108.78(14) . . ?
C19 C12 C11 119.36(16) . . ?
C19 C12 C13 133.63(15) . . ?
C11 C12 C13 107.00(14) . . ?
C18 C13 C14 119.34(17) . . ?
C18 C13 C12 133.44(16) . . ?
C14 C13 C12 107.22(14) . . ?
C15 C14 N1 129.93(16) . . ?
C15 C14 C13 121.67(15) . . ?
N1 C14 C13 108.36(15) . . ?
C16 C15 C14 117.36(18) . . ?
C15 C16 C17 121.65(19) . . ?
C18 C17 C16 121.00(17) . . ?
C17 C18 C13 118.93(17) . . ?
C22 C19 C12 119.15(15) . . ?
C21 C20 C22 121.44(17) . . ?
C11 C21 C20 117.54(16) . . ?
C19 C22 C20 120.81(16) . . ?
C24 C23 C5 119.75(16) . . ?
C25 C24 C23 120.42(16) . . ?
C24 C25 C7 119.62(17) . . ?

_refine_diff_density_max         0.431
_refine_diff_density_min         -0.684
_refine_diff_density_rms         0.107

