# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_4al
_database_code_depnum_ccdc_archive 'CCDC 2058196'
loop_
_audit_author_name
_audit_author_address
'Bella Chan'
;The Chinese University of Hong Kong
Hong Kong
;
_audit_update_record             
;
2021-02-20 deposited with the CCDC.	2021-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H27.50 N2 O1.75'
_chemical_formula_weight         504.09

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                   25.134(2)
_cell_length_b                   7.8986(6)
_cell_length_c                   30.550(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.564(4)
_cell_angle_gamma                90
_cell_volume                     6062.8(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    301(2)
_cell_measurement_reflns_used    247
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.105
_exptl_crystal_F_000             2124
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.068
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6762
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      301(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            95475
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_av_R_equivalents  0.1044
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.071
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5510
_reflns_number_gt                3527
_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 D8VENTURE DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_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)+(0.1749P)²+4.9657P] 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         5510
_refine_ls_number_parameters     370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1289
_refine_ls_R_factor_gt           0.0826
_refine_ls_wR_factor_ref         0.2952
_refine_ls_wR_factor_gt          0.2568
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001

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 0.27708(14) 0.0012(4) -0.07798(11) 0.0879(10) Uani 1 1 d . . . . .
N1 N 0.36466(11) 0.3619(3) 0.00707(9) 0.0457(7) Uani 1 1 d . . . . .
N2 N 0.38979(12) 0.4471(4) 0.07715(9) 0.0584(8) Uani 1 1 d . . . . .
C1 C 0.36413(13) 0.3447(4) 0.05268(11) 0.0463(8) Uani 1 1 d . . . . .
C2 C 0.33160(13) 0.1934(4) 0.06013(11) 0.0462(8) Uani 1 1 d . . . . .
C3 C 0.32054(16) 0.1104(5) 0.09886(13) 0.0609(10) Uani 1 1 d . . . . .
H3A H 0.3333 0.1514 0.1257 0.073 Uiso 1 1 calc R U . . .
C4 C 0.29009(17) -0.0348(5) 0.09633(15) 0.0700(12) Uani 1 1 d . . . . .
H4A H 0.2829 -0.0938 0.1218 0.084 Uiso 1 1 calc R U . . .
C5 C 0.27027(17) -0.0937(5) 0.05703(15) 0.0669(11) Uani 1 1 d . . . . .
H5A H 0.2494 -0.1908 0.0564 0.080 Uiso 1 1 calc R U . . .
C6 C 0.28083(14) -0.0112(4) 0.01836(14) 0.0568(10) Uani 1 1 d . . . . .
H6A H 0.2666 -0.0507 -0.0082 0.068 Uiso 1 1 calc R U . . .
C7 C 0.31284(12) 0.1310(4) 0.01978(11) 0.0442(8) Uani 1 1 d . . . . .
C8 C 0.33355(12) 0.2400(4) -0.01493(11) 0.0418(8) Uani 1 1 d . . . . .
C9 C 0.38531(15) 0.4351(5) 0.12328(11) 0.0546(10) Uani 1 1 d . . . . .
C10 C 0.42580(16) 0.3670(6) 0.14870(13) 0.0683(11) Uani 1 1 d . . . . .
H10A H 0.4564 0.3272 0.1356 0.082 Uiso 1 1 calc R U . . .
C11 C 0.42138(17) 0.3571(6) 0.19382(13) 0.0722(12) Uani 1 1 d . . . . .
H11A H 0.4490 0.3096 0.2106 0.087 Uiso 1 1 calc R U . . .
C12 C 0.37663(16) 0.4167(5) 0.21423(12) 0.0628(11) Uani 1 1 d . . . . .
C13 C 0.33671(18) 0.4879(6) 0.18816(13) 0.0696(11) Uani 1 1 d . . . . .
H13A H 0.3063 0.5295 0.2011 0.084 Uiso 1 1 calc R U . . .
C14 C 0.34117(17) 0.4982(6) 0.14330(12) 0.0662(11) Uani 1 1 d . . . . .
H14A H 0.3141 0.5483 0.1265 0.079 Uiso 1 1 calc R U . . .
C15 C 0.37059(19) 0.3978(6) 0.26211(13) 0.0727(12) Uani 1 1 d . . . . .
C16 C 0.4129(2) 0.4298(8) 0.29108(15) 0.0976(17) Uani 1 1 d . . . . .
H16A H 0.4453 0.4658 0.2804 0.117 Uiso 1 1 calc R U . . .
C17 C 0.4074(4) 0.4087(9) 0.33575(18) 0.122(2) Uani 1 1 d . . . . .
H17A H 0.4361 0.4309 0.3547 0.147 Uiso 1 1 calc R U . . .
C18 C 0.3607(4) 0.3563(10) 0.35204(19) 0.134(3) Uani 1 1 d . . . . .
H18A H 0.3571 0.3453 0.3821 0.160 Uiso 1 1 calc R U . . .
C19 C 0.3187(3) 0.3195(9) 0.3245(2) 0.126(2) Uani 1 1 d . . . . .
H19A H 0.2870 0.2797 0.3357 0.151 Uiso 1 1 calc R U . . .
C20 C 0.3232(2) 0.3417(8) 0.27917(15) 0.0962(17) Uani 1 1 d . . . . .
H20A H 0.2943 0.3186 0.2605 0.115 Uiso 1 1 calc R U . . .
C21 C 0.39207(12) 0.4989(4) -0.01335(10) 0.0400(8) Uani 1 1 d . . . . .
C22 C 0.36927(13) 0.6571(4) -0.01429(12) 0.0505(9) Uani 1 1 d . . . . .
H22A H 0.3361 0.6746 -0.0023 0.061 Uiso 1 1 calc R U . . .
C23 C 0.39605(13) 0.7899(4) -0.03324(12) 0.0496(9) Uani 1 1 d . . . . .
H23A H 0.3803 0.8965 -0.0342 0.059 Uiso 1 1 calc R U . . .
C24 C 0.44563(12) 0.7678(4) -0.05079(10) 0.0407(8) Uani 1 1 d . . . . .
C25 C 0.46796(13) 0.6072(4) -0.04944(11) 0.0460(8) Uani 1 1 d . . . . .
H25A H 0.5015 0.5897 -0.0608 0.055 Uiso 1 1 calc R U . . .
C26 C 0.44095(13) 0.4725(4) -0.03134(11) 0.0449(8) Uani 1 1 d . . . . .
H26A H 0.4558 0.3647 -0.0314 0.054 Uiso 1 1 calc R U . . .
C27 C 0.47384(13) 0.9127(4) -0.07037(11) 0.0468(8) Uani 1 1 d . . . . .
C28 C 0.52467(16) 0.9577(5) -0.05735(14) 0.0652(11) Uani 1 1 d . . . . .
H28A H 0.5425 0.8929 -0.0362 0.078 Uiso 1 1 calc R U . . .
C29 C 0.55000(19) 1.0964(6) -0.07478(17) 0.0795(14) Uani 1 1 d . . . . .
H29A H 0.5843 1.1248 -0.0653 0.095 Uiso 1 1 calc R U . . .
C30 C 0.5242(2) 1.1906(6) -0.10582(19) 0.0925(16) Uani 1 1 d . . . . .
H30A H 0.5411 1.2837 -0.1179 0.111 Uiso 1 1 calc R U . . .
C31 C 0.4739(2) 1.1500(7) -0.11943(19) 0.1012(18) Uani 1 1 d . . . . .
H31A H 0.4566 1.2150 -0.1408 0.121 Uiso 1 1 calc R U . . .
C32 C 0.44846(18) 1.0127(6) -0.10166(16) 0.0792(14) Uani 1 1 d . . . . .
H32A H 0.4138 0.9871 -0.1108 0.095 Uiso 1 1 calc R U . . .
C33 C 0.32867(13) 0.2419(4) -0.05928(11) 0.0485(9) Uani 1 1 d . . . . .
H33A H 0.3459 0.3312 -0.0728 0.058 Uiso 1 1 calc R U . . .
C34 C 0.30084(15) 0.1272(5) -0.08898(13) 0.0581(10) Uani 1 1 d . . . . .
C35 C 0.30339(19) 0.1722(6) -0.13670(14) 0.0783(13) Uani 1 1 d . . . . .
H35A H 0.3235 0.2746 -0.1399 0.118 Uiso 1 1 calc R U . . .
H35B H 0.3203 0.0821 -0.1522 0.118 Uiso 1 1 calc R U . . .
H35C H 0.2680 0.1885 -0.1485 0.118 Uiso 1 1 calc R U . . .
O1W O 0.5855(7) 1.1074(18) -0.1921(5) 0.111(5) Uani 0.25 1 d . . P . .
O2W O 0.5840(6) 1.032(2) -0.2791(5) 0.117(5) Uani 0.25 1 d . . P . .
O3W O 0.6783(6) 1.071(2) -0.2317(6) 0.125(6) Uani 0.25 1 d . . P . .


_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 C34 1.213(5) . ?
N1 C1 1.401(4) . ?
N1 C8 1.401(4) . ?
N1 C21 1.434(4) . ?
N2 C1 1.266(4) . ?
N2 C9 1.420(5) . ?
C1 C2 1.469(5) . ?
C2 C3 1.387(5) . ?
C2 C7 1.398(5) . ?
C3 C4 1.380(5) . ?
C4 C5 1.369(6) . ?
C5 C6 1.381(6) . ?
C6 C7 1.382(5) . ?
C7 C8 1.472(4) . ?
C8 C33 1.357(5) . ?
C9 C10 1.373(6) . ?
C9 C14 1.375(5) . ?
C10 C11 1.388(6) . ?
C11 C12 1.384(6) . ?
C12 C13 1.383(6) . ?
C12 C15 1.482(6) . ?
C13 C14 1.381(6) . ?
C15 C20 1.385(7) . ?
C15 C16 1.388(7) . ?
C16 C17 1.386(8) . ?
C17 C18 1.353(10) . ?
C18 C19 1.363(11) . ?
C19 C20 1.403(7) . ?
C21 C22 1.375(5) . ?
C21 C26 1.375(4) . ?
C22 C23 1.382(5) . ?
C23 C24 1.381(5) . ?
C24 C25 1.387(5) . ?
C24 C27 1.481(4) . ?
C25 C26 1.385(5) . ?
C27 C28 1.374(5) . ?
C27 C32 1.383(5) . ?
C28 C29 1.381(6) . ?
C29 C30 1.356(7) . ?
C30 C31 1.359(7) . ?
C31 C32 1.377(6) . ?
C33 C34 1.449(5) . ?
C34 C35 1.503(6) . ?

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
C1 N1 C8 113.0(2) . . ?
C1 N1 C21 121.6(3) . . ?
C8 N1 C21 125.3(3) . . ?
C1 N2 C9 119.4(3) . . ?
N2 C1 N1 120.4(3) . . ?
N2 C1 C2 134.8(3) . . ?
N1 C1 C2 104.7(3) . . ?
C3 C2 C7 121.0(3) . . ?
C3 C2 C1 129.9(3) . . ?
C7 C2 C1 109.0(3) . . ?
C4 C3 C2 117.9(4) . . ?
C5 C4 C3 121.3(4) . . ?
C4 C5 C6 121.1(4) . . ?
C5 C6 C7 118.8(4) . . ?
C6 C7 C2 119.8(3) . . ?
C6 C7 C8 132.1(3) . . ?
C2 C7 C8 108.2(3) . . ?
C33 C8 N1 120.3(3) . . ?
C33 C8 C7 134.6(3) . . ?
N1 C8 C7 105.1(3) . . ?
C10 C9 C14 119.0(3) . . ?
C10 C9 N2 120.7(4) . . ?
C14 C9 N2 120.3(3) . . ?
C9 C10 C11 120.4(4) . . ?
C12 C11 C10 121.1(4) . . ?
C13 C12 C11 117.7(4) . . ?
C13 C12 C15 121.1(4) . . ?
C11 C12 C15 121.1(4) . . ?
C14 C13 C12 121.2(4) . . ?
C9 C14 C13 120.6(4) . . ?
C20 C15 C16 118.0(4) . . ?
C20 C15 C12 121.1(4) . . ?
C16 C15 C12 120.9(4) . . ?
C17 C16 C15 120.8(6) . . ?
C18 C17 C16 120.6(6) . . ?
C17 C18 C19 120.2(6) . . ?
C18 C19 C20 120.1(7) . . ?
C15 C20 C19 120.3(6) . . ?
C22 C21 C26 120.4(3) . . ?
C22 C21 N1 119.3(3) . . ?
C26 C21 N1 120.3(3) . . ?
C21 C22 C23 119.4(3) . . ?
C24 C23 C22 121.5(3) . . ?
C23 C24 C25 118.2(3) . . ?
C23 C24 C27 120.4(3) . . ?
C25 C24 C27 121.4(3) . . ?
C26 C25 C24 120.8(3) . . ?
C21 C26 C25 119.8(3) . . ?
C28 C27 C32 117.4(3) . . ?
C28 C27 C24 122.3(3) . . ?
C32 C27 C24 120.3(3) . . ?
C27 C28 C29 121.9(4) . . ?
C30 C29 C28 119.2(4) . . ?
C29 C30 C31 120.4(4) . . ?
C30 C31 C32 120.2(5) . . ?
C31 C32 C27 120.8(4) . . ?
C8 C33 C34 130.3(3) . . ?
O1 C34 C33 124.9(4) . . ?
O1 C34 C35 119.8(3) . . ?
C33 C34 C35 115.3(3) . . ?

_refine_diff_density_max         0.784
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.090

_shelxl_version_number           2014/6


# start Validation Reply Form
_vrf_PLAT430_4al                 
;
PROBLEM: Short Inter D...A Contact O1W ..O3W . 2.67 Ang.
RESPONSE: The H atoms of the water molecules cannot be located from the data.
;
# end Validation Reply Form


