# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Sciences.
# This journal is © The Royal Society of Chemistry and Owner Societies 2020

####################################################################### 
# 
# 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_m725b
_database_code_depnum_ccdc_archive 'CCDC 1998515'
loop_
_audit_author_name
_audit_author_address
'Jerome Marrot'
;Institut Lavoisier de Versailles
France
;
_audit_update_record             
;
2020-04-22 deposited with the CCDC.	2020-07-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H25 N O'
_chemical_formula_weight         499.58

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   31.8763(12)
_cell_length_b                   6.7502(2)
_cell_length_c                   27.2595(10)
_cell_angle_alpha                90
_cell_angle_beta                 114.087(2)
_cell_angle_gamma                90
_cell_volume                     5354.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9828
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      25.03

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_F_000             2096
_exptl_transmission_factor_min   0.6969
_exptl_transmission_factor_max   0.7331
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Sheldrick, V2008/1)'

_exptl_special_details           
; 
  'Blessing, Acta Cryst. (1995) A51, 33-38'  
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            185603
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.637
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_full        25.049
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4721
_reflns_number_gt                4329
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0499P)²+3.1442P] 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         4721
_refine_ls_number_parameters     352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_ref         0.1351
_refine_ls_wR_factor_gt          0.1323
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_restrained_S_all      1.170
_refine_ls_shift/su_max          0.001
_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
O1 O 0.63488(4) 0.03308(18) 0.16262(5) 0.0567(3) Uani 1 1 d . . . . .
C2 C 0.67866(6) -0.0130(2) 0.16924(6) 0.0484(4) Uani 1 1 d . . . . .
C3 C 0.69563(7) -0.1936(3) 0.19487(7) 0.0567(5) Uani 1 1 d . . . . .
H3 H 0.676328 -0.281686 0.201905 0.068 Uiso 1 1 calc R U . . .
C4 C 0.74035(7) -0.2384(3) 0.20924(7) 0.0585(5) Uani 1 1 d . . . . .
H4 H 0.751602 -0.357348 0.226920 0.070 Uiso 1 1 calc R U . . .
C5 C 0.77054(7) -0.1116(3) 0.19844(7) 0.0550(5) Uani 1 1 d . . . . .
C6 C 0.81824(7) -0.1578(3) 0.21942(8) 0.0672(5) Uani 1 1 d . . . . .
H6 H 0.828347 -0.277802 0.237085 0.081 Uiso 1 1 calc R U . . .
C7 C 0.84910(8) -0.0327(4) 0.21439(9) 0.0727(6) Uani 1 1 d . . . . .
H7 H 0.880404 -0.059876 0.230761 0.087 Uiso 1 1 calc R U . . .
C8 C 0.83277(7) 0.1404(3) 0.18369(8) 0.0627(5) Uani 1 1 d . . . . .
C9 C 0.85718(7) 0.2927(3) 0.16968(8) 0.0672(5) Uani 1 1 d . . . . .
C10 C 0.90402(8) 0.3241(5) 0.18221(10) 0.0879(7) Uani 1 1 d . . . . .
H10 H 0.926259 0.238247 0.204993 0.106 Uiso 1 1 calc R U . . .
C11 C 0.91613(10) 0.4850(5) 0.15996(11) 0.0992(9) Uani 1 1 d . . . . .
H11 H 0.946936 0.507340 0.167481 0.119 Uiso 1 1 calc R U . . .
C12 C 0.88333(10) 0.6134(5) 0.12668(11) 0.0943(8) Uani 1 1 d . . . . .
H12 H 0.892625 0.721003 0.112251 0.113 Uiso 1 1 calc R U . . .
C13 C 0.83732(8) 0.5880(4) 0.11408(9) 0.0779(6) Uani 1 1 d . . . . .
H13 H 0.815516 0.676105 0.091570 0.093 Uiso 1 1 calc R U . . .
C14 C 0.82459(7) 0.4252(3) 0.13634(7) 0.0622(5) Uani 1 1 d . . . . .
N15 N 0.78052(5) 0.3628(2) 0.12972(6) 0.0562(4) Uani 1 1 d . . . . .
C16 C 0.78610(6) 0.1862(3) 0.15974(7) 0.0527(4) Uani 1 1 d . . . . .
C17 C 0.75285(6) 0.0693(3) 0.16966(6) 0.0484(4) Uani 1 1 d . . . . .
C18 C 0.70616(6) 0.1208(2) 0.15748(6) 0.0466(4) Uani 1 1 d . . . . .
C19 C 0.68735(6) 0.3196(2) 0.14383(7) 0.0490(4) Uani 1 1 d . . . . .
H19 H 0.706788 0.423839 0.144890 0.059 Uiso 1 1 calc R U . . .
C20 C 0.64329(6) 0.3551(3) 0.12998(7) 0.0546(4) Uani 1 1 d . . . . .
H20 H 0.632425 0.484538 0.123450 0.066 Uiso 1 1 calc R U . . .
C21 C 0.61038(6) 0.1880(3) 0.12465(7) 0.0541(4) Uani 1 1 d . . . . .
C22 C 0.57240(6) 0.2554(3) 0.14137(8) 0.0611(5) Uani 1 1 d . . . . .
C23 C 0.54514(8) 0.4134(4) 0.11486(11) 0.0835(7) Uani 1 1 d . . . . .
H23 H 0.549097 0.471194 0.086066 0.100 Uiso 1 1 calc R U . . .
C24 C 0.51180(10) 0.4874(4) 0.13059(15) 0.1090(10) Uani 1 1 d . . . . .
H24 H 0.494015 0.595796 0.112969 0.131 Uiso 1 1 calc R U . . .
C25 C 0.50537(10) 0.3986(6) 0.17260(15) 0.1092(10) Uani 1 1 d . . . . .
H25 H 0.483175 0.446674 0.183470 0.131 Uiso 1 1 calc R U . . .
C26 C 0.53158(9) 0.2408(6) 0.19794(12) 0.1038(9) Uani 1 1 d . . . . .
H26 H 0.526901 0.179951 0.225902 0.125 Uiso 1 1 calc R U . . .
C27 C 0.56490(7) 0.1697(4) 0.18291(9) 0.0785(6) Uani 1 1 d . . . . .
H27 H 0.582674 0.061992 0.201033 0.094 Uiso 1 1 calc R U . . .
C28 C 0.58983(6) 0.0955(3) 0.06834(7) 0.0562(5) Uani 1 1 d . . . . .
C29 C 0.59285(8) 0.1870(4) 0.02491(8) 0.0777(6) Uani 1 1 d . . . . .
H29 H 0.607668 0.308581 0.029338 0.093 Uiso 1 1 calc R U . . .
C30 C 0.57401(9) 0.0998(5) -0.02541(9) 0.0939(8) Uani 1 1 d . . . . .
H30 H 0.576508 0.163005 -0.054409 0.113 Uiso 1 1 calc R U . . .
C31 C 0.55184(9) -0.0776(4) -0.03295(10) 0.0922(8) Uani 1 1 d . . . . .
H31 H 0.539170 -0.135561 -0.066833 0.111 Uiso 1 1 calc R U . . .
C32 C 0.54853(10) -0.1686(4) 0.00992(10) 0.0996(9) Uani 1 1 d . . . . .
H32 H 0.533572 -0.289956 0.005268 0.120 Uiso 1 1 calc R U . . .
C33 C 0.56713(9) -0.0827(3) 0.06005(9) 0.0826(7) Uani 1 1 d . . . . .
H33 H 0.564287 -0.146332 0.088803 0.099 Uiso 1 1 calc R U . . .
C34 C 0.74183(7) 0.4052(3) 0.08027(7) 0.0583(5) Uani 1 1 d . . . . .
C35 C 0.72199(7) 0.2554(3) 0.04361(8) 0.0671(5) Uani 1 1 d . . . . .
H35 H 0.732891 0.126229 0.051265 0.081 Uiso 1 1 calc R U . . .
C36 C 0.68570(8) 0.2993(5) -0.00463(9) 0.0871(8) Uani 1 1 d . . . . .
H36 H 0.672193 0.199232 -0.029552 0.105 Uiso 1 1 calc R U . . .
C37 C 0.66965(10) 0.4880(5) -0.01584(10) 0.1035(10) Uani 1 1 d . . . . .
H37 H 0.645375 0.516006 -0.048503 0.124 Uiso 1 1 calc R U . . .
C38 C 0.68892(10) 0.6374(4) 0.02059(11) 0.0985(8) Uani 1 1 d . . . . .
H38 H 0.677494 0.765713 0.012852 0.118 Uiso 1 1 calc R U . . .
C39 C 0.72536(8) 0.5963(3) 0.06880(9) 0.0762(6) Uani 1 1 d . . . . .
H39 H 0.738760 0.697249 0.093489 0.091 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
O1 C2 1.368(2) . ?
O1 C21 1.454(2) . ?
C2 C18 1.384(2) . ?
C2 C3 1.400(3) . ?
C3 C4 1.349(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.406(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.424(3) . ?
C5 C17 1.436(2) . ?
C6 C7 1.345(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.407(3) . ?
C7 H7 0.9300 . ?
C8 C16 1.394(3) . ?
C8 C9 1.432(3) . ?
C9 C14 1.391(3) . ?
C9 C10 1.405(3) . ?
C10 C11 1.373(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.374(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.393(3) . ?
C13 H13 0.9300 . ?
C14 N15 1.406(2) . ?
N15 C16 1.415(2) . ?
N15 C34 1.436(2) . ?
C16 C17 1.433(2) . ?
C17 C18 1.429(2) . ?
C18 C19 1.455(2) . ?
C19 C20 1.319(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.507(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.527(3) . ?
C21 C28 1.534(2) . ?
C22 C27 1.377(3) . ?
C22 C23 1.379(3) . ?
C23 C24 1.391(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.380(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.356(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.372(3) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C29 1.373(3) . ?
C28 C33 1.374(3) . ?
C29 C30 1.384(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.362(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.362(4) . ?
C31 H31 0.9300 . ?
C32 C33 1.376(3) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
C34 C39 1.380(3) . ?
C34 C35 1.380(3) . ?
C35 C36 1.383(3) . ?
C35 H35 0.9300 . ?
C36 C37 1.360(4) . ?
C36 H36 0.9300 . ?
C37 C38 1.372(4) . ?
C37 H37 0.9300 . ?
C38 C39 1.381(3) . ?
C38 H38 0.9300 . ?
C39 H39 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 O1 C21 118.68(13) . . ?
O1 C2 C18 121.99(16) . . ?
O1 C2 C3 115.43(15) . . ?
C18 C2 C3 122.11(17) . . ?
C4 C3 C2 119.15(17) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 122.36(17) . . ?
C3 C4 H4 118.8 . . ?
C5 C4 H4 118.8 . . ?
C4 C5 C6 119.51(18) . . ?
C4 C5 C17 118.83(17) . . ?
C6 C5 C17 121.51(18) . . ?
C7 C6 C5 121.80(19) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C7 C8 118.2(2) . . ?
C6 C7 H7 120.9 . . ?
C8 C7 H7 120.9 . . ?
C16 C8 C7 121.88(19) . . ?
C16 C8 C9 107.92(18) . . ?
C7 C8 C9 130.2(2) . . ?
C14 C9 C10 119.9(2) . . ?
C14 C9 C8 107.08(17) . . ?
C10 C9 C8 133.0(2) . . ?
C11 C10 C9 118.3(3) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
C10 C11 C12 121.0(2) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C13 C12 C11 122.2(2) . . ?
C13 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C12 C13 C14 117.4(2) . . ?
C12 C13 H13 121.3 . . ?
C14 C13 H13 121.3 . . ?
C9 C14 C13 121.3(2) . . ?
C9 C14 N15 109.37(17) . . ?
C13 C14 N15 129.3(2) . . ?
C14 N15 C16 107.17(16) . . ?
C14 N15 C34 119.40(15) . . ?
C16 N15 C34 124.59(15) . . ?
C8 C16 N15 108.43(16) . . ?
C8 C16 C17 121.29(17) . . ?
N15 C16 C17 130.17(17) . . ?
C18 C17 C16 127.04(16) . . ?
C18 C17 C5 118.23(16) . . ?
C16 C17 C5 114.56(16) . . ?
C2 C18 C17 119.05(16) . . ?
C2 C18 C19 115.28(16) . . ?
C17 C18 C19 124.40(15) . . ?
C20 C19 C18 121.33(16) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C19 C20 C21 120.66(17) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
O1 C21 C20 108.61(14) . . ?
O1 C21 C22 105.24(14) . . ?
C20 C21 C22 110.70(15) . . ?
O1 C21 C28 107.80(14) . . ?
C20 C21 C28 113.40(15) . . ?
C22 C21 C28 110.69(15) . . ?
C27 C22 C23 118.2(2) . . ?
C27 C22 C21 123.0(2) . . ?
C23 C22 C21 118.75(19) . . ?
C22 C23 C24 120.9(3) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C25 C24 C23 119.4(3) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C26 C25 C24 119.7(3) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C25 C26 C27 120.9(3) . . ?
C25 C26 H26 119.5 . . ?
C27 C26 H26 119.5 . . ?
C26 C27 C22 120.9(3) . . ?
C26 C27 H27 119.5 . . ?
C22 C27 H27 119.5 . . ?
C29 C28 C33 118.00(19) . . ?
C29 C28 C21 121.89(17) . . ?
C33 C28 C21 120.10(17) . . ?
C28 C29 C30 120.6(2) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 H29 119.7 . . ?
C31 C30 C29 120.8(2) . . ?
C31 C30 H30 119.6 . . ?
C29 C30 H30 119.6 . . ?
C32 C31 C30 119.0(2) . . ?
C32 C31 H31 120.5 . . ?
C30 C31 H31 120.5 . . ?
C31 C32 C33 120.6(2) . . ?
C31 C32 H32 119.7 . . ?
C33 C32 H32 119.7 . . ?
C28 C33 C32 121.1(2) . . ?
C28 C33 H33 119.4 . . ?
C32 C33 H33 119.4 . . ?
C39 C34 C35 120.1(2) . . ?
C39 C34 N15 120.04(18) . . ?
C35 C34 N15 119.84(19) . . ?
C34 C35 C36 119.3(2) . . ?
C34 C35 H35 120.4 . . ?
C36 C35 H35 120.4 . . ?
C37 C36 C35 120.4(2) . . ?
C37 C36 H36 119.8 . . ?
C35 C36 H36 119.8 . . ?
C36 C37 C38 120.6(2) . . ?
C36 C37 H37 119.7 . . ?
C38 C37 H37 119.7 . . ?
C37 C38 C39 119.7(3) . . ?
C37 C38 H38 120.1 . . ?
C39 C38 H38 120.1 . . ?
C34 C39 C38 119.9(2) . . ?
C34 C39 H39 120.1 . . ?
C38 C39 H39 120.1 . . ?

_refine_diff_density_max         0.136
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.030

