# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_ms35m
_database_code_depnum_ccdc_archive 'CCDC 2038554'
loop_
_audit_author_name
_audit_author_address
'mihaiela stuparu'
;Nanyang Technological University 
Singapore
;
_audit_update_record             
;
2020-10-15 deposited with the CCDC.	2021-01-25 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H17 N'
_chemical_formula_iupac          ?
_chemical_formula_weight         427.48

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   9.5983(12)
_cell_length_b                   7.4141(8)
_cell_length_c                   28.155(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.017(4)
_cell_angle_gamma                90
_cell_volume                     1988.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1279
_cell_measurement_theta_min      2.4360
_cell_measurement_theta_max      24.6304
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888

_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            22550
_diffrn_reflns_av_R_equivalents  0.1749
_diffrn_reflns_av_unetI/netI     0.2034
_diffrn_reflns_theta_min         2.44
_diffrn_reflns_theta_max         31.00
_diffrn_reflns_theta_full        31.00
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       36

_refine_special_details          
;
;

_reflns_number_total             6327
_reflns_number_gt                2631
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.2157
_refine_ls_R_factor_gt           0.0790
_refine_ls_wR_factor_gt          0.1342
_refine_ls_wR_factor_ref         0.1857
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_restrained_S_all      0.982
_refine_ls_number_reflns         6327
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0583P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.326
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2018)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2018)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.3370(3) 0.6332(3) 0.12614(10) 0.0209(6) Uani d . . . 1 . .
C C2 0.1976(3) 0.5952(3) 0.10661(10) 0.0207(6) Uani d . . . 1 . .
C C3 0.1124(3) 0.5979(4) 0.14408(10) 0.0202(6) Uani d . . . 1 . .
C C4 0.1996(3) 0.6411(4) 0.18714(10) 0.0199(6) Uani d . . . 1 . .
C C5 0.3400(3) 0.6620(4) 0.17574(10) 0.0209(6) Uani d . . . 1 . .
C C6 0.4572(3) 0.6364(4) 0.20830(10) 0.0206(6) Uani d . . . 1 . .
C C7 0.5816(3) 0.5941(4) 0.18594(10) 0.0235(7) Uani d . . . 1 . .
H H7 0.669046 0.584572 0.205625 0.028 Uiso calc U . R 1 . .
C C8 0.5786(3) 0.5669(4) 0.13724(11) 0.0237(7) Uani d . . . 1 . .
H H8 0.663749 0.540008 0.124744 0.028 Uiso calc U . R 1 . .
C C9 0.4514(3) 0.5779(4) 0.10500(10) 0.0226(7) Uani d . . . 1 . .
C C10 0.4176(3) 0.5044(4) 0.05751(10) 0.0234(6) Uani d . . . 1 . .
H H10 0.491584 0.482226 0.038729 0.028 Uiso calc U . R 1 . .
C C11 0.2815(3) 0.4652(4) 0.03841(11) 0.0249(7) Uani d . . . 1 . .
H H11 0.264286 0.416624 0.007017 0.03 Uiso calc U . R 1 . .
C C12 0.1645(3) 0.4969(4) 0.06544(10) 0.0235(7) Uani d . . . 1 . .
C C13 0.0273(3) 0.4142(4) 0.06074(11) 0.0248(7) Uani d . . . 1 . .
H H13 -0.008212 0.359258 0.03124 0.03 Uiso calc U . R 1 . .
C C14 -0.0536(3) 0.4130(4) 0.09814(11) 0.0252(7) Uani d . . . 1 . .
H H14 -0.142388 0.354585 0.093751 0.03 Uiso calc U . R 1 . .
C C15 -0.0081(3) 0.4973(4) 0.14362(10) 0.0209(6) Uani d . . . 1 . .
C C16 -0.0500(3) 0.4607(4) 0.19019(10) 0.0233(7) Uani d . . . 1 . .
H H16 -0.138231 0.405057 0.192219 0.028 Uiso calc U . R 1 . .
C C17 0.0346(3) 0.5043(4) 0.23192(11) 0.0229(6) Uani d . . . 1 . .
H H17 0.002708 0.478589 0.261843 0.027 Uiso calc U . R 1 . .
C C18 0.1705(3) 0.5881(4) 0.23116(10) 0.0206(6) Uani d . . . 1 . .
C C19 0.2891(3) 0.5924(4) 0.26896(10) 0.0200(6) Uani d . . . 1 . .
C C20 0.4297(3) 0.6212(3) 0.25860(10) 0.0196(6) Uani d . . . 1 . .
C C21 0.5367(3) 0.6214(3) 0.29900(10) 0.0200(6) Uani d . . . 1 . .
C C22 0.6794(3) 0.6652(4) 0.29487(11) 0.0239(7) Uani d . . . 1 . .
H H22 0.703749 0.709553 0.265317 0.029 Uiso calc U . R 1 . .
C C23 0.7818(3) 0.6445(4) 0.33280(11) 0.0263(7) Uani d . . . 1 . .
H H23 0.876542 0.671678 0.329052 0.032 Uiso calc U . R 1 . .
C C24 0.7484(3) 0.5841(4) 0.37677(11) 0.0256(7) Uani d . . . 1 . .
H H24 0.820722 0.564058 0.402396 0.031 Uiso calc U . R 1 . .
C C25 0.6111(3) 0.5536(4) 0.38316(11) 0.0244(7) Uani d . . . 1 . .
H H25 0.588832 0.516986 0.413673 0.029 Uiso calc U . R 1 . .
C C26 0.5018(3) 0.5757(3) 0.34488(10) 0.0205(6) Uani d . . . 1 . .
C C27 0.3562(3) 0.5519(4) 0.35058(10) 0.0210(6) Uani d . . . 1 . .
C C28 0.3024(3) 0.5206(4) 0.39726(10) 0.0218(6) Uani d . . . 1 . .
C C29 0.1850(3) 0.4085(4) 0.39827(11) 0.0241(7) Uani d . . . 1 . .
H H29 0.146675 0.347497 0.369995 0.029 Uiso calc U . R 1 . .
C C30 0.1248(3) 0.3862(4) 0.43992(11) 0.0268(7) Uani d . . . 1 . .
H H30 0.045388 0.309771 0.440046 0.032 Uiso calc U . R 1 . .
C C31 0.1789(3) 0.4741(4) 0.48165(11) 0.0268(7) Uani d . . . 1 . .
H H31 0.137061 0.457951 0.510231 0.032 Uiso calc U . R 1 . .
C C32 0.2953(3) 0.5863(4) 0.48123(11) 0.0280(7) Uani d . . . 1 . .
H H32 0.333209 0.647517 0.509534 0.034 Uiso calc U . R 1 . .
C C33 0.3553(3) 0.6080(4) 0.43930(10) 0.0255(7) Uani d . . . 1 . .
H H33 0.434639 0.684595 0.439265 0.031 Uiso calc U . R 1 . .
N N1 0.2560(2) 0.5611(3) 0.31403(8) 0.0214(5) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C9 . 1.374(4) ?
C1 C5 . 1.410(4) ?
C1 C2 . 1.412(4) ?
C2 C12 . 1.373(4) ?
C2 C3 . 1.411(4) ?
C3 C15 . 1.375(4) ?
C3 C4 . 1.423(4) ?
C4 C18 . 1.361(4) ?
C4 C5 . 1.431(4) ?
C5 C6 . 1.374(4) ?
C6 C7 . 1.451(4) ?
C6 C20 . 1.476(4) ?
C7 C8 . 1.383(4) ?
C7 H7 . 0.95 ?
C8 C9 . 1.432(4) ?
C8 H8 . 0.95 ?
C9 C10 . 1.444(4) ?
C10 C11 . 1.381(4) ?
C10 H10 . 0.95 ?
C11 C12 . 1.451(4) ?
C11 H11 . 0.95 ?
C12 C13 . 1.444(4) ?
C13 C14 . 1.383(4) ?
C13 H13 . 0.95 ?
C14 C15 . 1.444(4) ?
C14 H14 . 0.95 ?
C15 C16 . 1.444(4) ?
C16 C17 . 1.382(4) ?
C16 H16 . 0.95 ?
C17 C18 . 1.448(4) ?
C17 H17 . 0.95 ?
C18 C19 . 1.460(4) ?
C19 N1 . 1.365(3) ?
C19 C20 . 1.432(4) ?
C20 C21 . 1.436(4) ?
C21 C26 . 1.415(4) ?
C21 C22 . 1.426(4) ?
C22 C23 . 1.369(4) ?
C22 H22 . 0.95 ?
C23 C24 . 1.390(4) ?
C23 H23 . 0.95 ?
C24 C25 . 1.370(4) ?
C24 H24 . 0.95 ?
C25 C26 . 1.419(4) ?
C25 H25 . 0.95 ?
C26 C27 . 1.437(4) ?
C27 N1 . 1.322(3) ?
C27 C28 . 1.488(4) ?
C28 C33 . 1.390(4) ?
C28 C29 . 1.403(4) ?
C29 C30 . 1.380(4) ?
C29 H29 . 0.95 ?
C30 C31 . 1.388(4) ?
C30 H30 . 0.95 ?
C31 C32 . 1.394(4) ?
C31 H31 . 0.95 ?
C32 C33 . 1.385(4) ?
C32 H32 . 0.95 ?
C33 H33 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 C1 C5 . . 123.6(3) ?
C9 C1 C2 . . 122.8(3) ?
C5 C1 C2 . . 108.6(2) ?
C12 C2 C3 . . 122.9(3) ?
C12 C2 C1 . . 123.0(3) ?
C3 C2 C1 . . 108.3(3) ?
C15 C3 C2 . . 123.2(3) ?
C15 C3 C4 . . 122.5(3) ?
C2 C3 C4 . . 107.8(2) ?
C18 C4 C3 . . 123.1(3) ?
C18 C4 C5 . . 122.6(3) ?
C3 C4 C5 . . 107.8(2) ?
C6 C5 C1 . . 123.8(3) ?
C6 C5 C4 . . 123.5(3) ?
C1 C5 C4 . . 107.5(2) ?
C5 C6 C7 . . 113.0(3) ?
C5 C6 C20 . . 115.0(2) ?
C7 C6 C20 . . 130.7(3) ?
C8 C7 C6 . . 122.9(3) ?
C8 C7 H7 . . 118.6 ?
C6 C7 H7 . . 118.6 ?
C7 C8 C9 . . 122.3(3) ?
C7 C8 H8 . . 118.9 ?
C9 C8 H8 . . 118.9 ?
C1 C9 C8 . . 114.0(3) ?
C1 C9 C10 . . 114.4(3) ?
C8 C9 C10 . . 130.0(3) ?
C11 C10 C9 . . 122.3(3) ?
C11 C10 H10 . . 118.8 ?
C9 C10 H10 . . 118.8 ?
C10 C11 C12 . . 121.2(3) ?
C10 C11 H11 . . 119.4 ?
C12 C11 H11 . . 119.4 ?
C2 C12 C13 . . 114.6(3) ?
C2 C12 C11 . . 114.5(3) ?
C13 C12 C11 . . 129.7(3) ?
C14 C13 C12 . . 121.6(3) ?
C14 C13 H13 . . 119.2 ?
C12 C13 H13 . . 119.2 ?
C13 C14 C15 . . 122.3(3) ?
C13 C14 H14 . . 118.8 ?
C15 C14 H14 . . 118.8 ?
C3 C15 C16 . . 114.9(3) ?
C3 C15 C14 . . 114.0(3) ?
C16 C15 C14 . . 129.5(3) ?
C17 C16 C15 . . 121.9(3) ?
C17 C16 H16 . . 119.1 ?
C15 C16 H16 . . 119.1 ?
C16 C17 C18 . . 121.6(3) ?
C16 C17 H17 . . 119.2 ?
C18 C17 H17 . . 119.2 ?
C4 C18 C17 . . 115.0(3) ?
C4 C18 C19 . . 115.4(3) ?
C17 C18 C19 . . 128.5(3) ?
N1 C19 C20 . . 123.2(3) ?
N1 C19 C18 . . 115.1(2) ?
C20 C19 C18 . . 121.7(2) ?
C19 C20 C21 . . 116.1(2) ?
C19 C20 C6 . . 119.3(2) ?
C21 C20 C6 . . 124.5(2) ?
C26 C21 C22 . . 117.8(3) ?
C26 C21 C20 . . 119.8(2) ?
C22 C21 C20 . . 122.4(3) ?
C23 C22 C21 . . 121.1(3) ?
C23 C22 H22 . . 119.5 ?
C21 C22 H22 . . 119.5 ?
C22 C23 C24 . . 120.6(3) ?
C22 C23 H23 . . 119.7 ?
C24 C23 H23 . . 119.7 ?
C25 C24 C23 . . 120.0(3) ?
C25 C24 H24 . . 120.0 ?
C23 C24 H24 . . 120.0 ?
C24 C25 C26 . . 121.0(3) ?
C24 C25 H25 . . 119.5 ?
C26 C25 H25 . . 119.5 ?
C21 C26 C25 . . 119.0(3) ?
C21 C26 C27 . . 118.3(3) ?
C25 C26 C27 . . 122.7(3) ?
N1 C27 C26 . . 122.1(3) ?
N1 C27 C28 . . 113.4(2) ?
C26 C27 C28 . . 124.4(3) ?
C33 C28 C29 . . 118.0(3) ?
C33 C28 C27 . . 123.3(3) ?
C29 C28 C27 . . 118.5(3) ?
C30 C29 C28 . . 120.6(3) ?
C30 C29 H29 . . 119.7 ?
C28 C29 H29 . . 119.7 ?
C29 C30 C31 . . 120.7(3) ?
C29 C30 H30 . . 119.6 ?
C31 C30 H30 . . 119.6 ?
C30 C31 C32 . . 119.4(3) ?
C30 C31 H31 . . 120.3 ?
C32 C31 H31 . . 120.3 ?
C33 C32 C31 . . 119.6(3) ?
C33 C32 H32 . . 120.2 ?
C31 C32 H32 . . 120.2 ?
C32 C33 C28 . . 121.7(3) ?
C32 C33 H33 . . 119.2 ?
C28 C33 H33 . . 119.2 ?
C27 N1 C19 . . 120.2(2) ?



