# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_glo10557
_database_code_depnum_ccdc_archive 'CCDC 2334460'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut University of Muenster
Germany
;
_audit_update_record             
;
2024-02-22 deposited with the CCDC.	2024-08-26 downloaded from the CCDC.
;

_audit_creation_method           'APEX4 v2022.10-1'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H23 N O'
_chemical_formula_iupac          ?
_chemical_formula_weight         353.44

_chemical_melting_point          ?

_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                   16.5300(3)
_cell_length_b                   5.94310(10)
_cell_length_c                   20.4998(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.4490(10)
_cell_angle_gamma                90
_cell_volume                     1886.98(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8534
_cell_measurement_theta_min      2.9743
_cell_measurement_theta_max      66.3808
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            orange-yellow
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.074
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752

_exptl_absorpt_coefficient_mu    0.581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10. doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.96

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'
_diffrn_source_power             0.05
_diffrn_source_current           1.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device       'Bruker D8 Venture Photon III'
_diffrn_measurement_device_type  'single crystal diffractometer'
_diffrn_measurement_method       'phi/omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            29807
_diffrn_reflns_av_R_equivalents  0.0909
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         66.68
_diffrn_reflns_theta_full        66.68
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24

_refine_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_number_total             3305
_reflns_number_gt                2617
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.1030
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_number_reflns         3305
_refine_ls_number_parameters     244
_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)+(0.0388P)²+0.8721P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.181
_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 0.0181 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'

_computing_data_collection       'Bruker APEX4 v2022.10-1 Photon III'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2019/1 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1380)'
_computing_publication_material  'SHELXT 2011/1 (Sheldrick, 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
N N1 0.45162(8) 0.4429(2) 0.69906(7) 0.0216(3) Uani d . . . 1 . .
O O1 0.32991(9) -0.4315(2) 0.43745(7) 0.0409(4) Uani d . . . 1 . .
C C1 0.37214(13) -0.2953(3) 0.48088(10) 0.0322(4) Uani d . . . 1 . .
H H1 0.432998 -0.315114 0.498522 0.039000 Uiso calc U . R 1 . .
C C2 0.33776(11) -0.1063(3) 0.50790(9) 0.0266(4) Uani d . . . 1 . .
C C3 0.39672(11) 0.0199(3) 0.55822(9) 0.0261(4) Uani d . . . 1 . .
H H3 0.455310 -0.023013 0.568972 0.031000 Uiso calc U . R 1 . .
C C4 0.38305(11) 0.2058(3) 0.59670(9) 0.0248(4) Uani d . . . 1 . .
H H4 0.328330 0.277693 0.583231 0.030000 Uiso calc U . R 1 . .
C C5 0.44963(11) 0.2790(3) 0.65318(9) 0.0228(4) Uani d . . . 1 . .
H H5 0.502846 0.202872 0.661527 0.027000 Uiso calc U . R 1 . .
C C6 0.53369(10) 0.4988(3) 0.75376(8) 0.0232(4) Uani d . . . 1 . .
H H6A 0.571084 0.363692 0.763826 0.028000 Uiso calc U . R 1 . .
H H6B 0.522232 0.537410 0.796703 0.028000 Uiso calc U . R 1 . .
C C7 0.38040(10) 0.6041(3) 0.68719(8) 0.0237(4) Uani d . . . 1 . .
H H7A 0.326441 0.536379 0.655102 0.028000 Uiso calc U . R 1 . .
H H7B 0.392682 0.740693 0.664615 0.028000 Uiso calc U . R 1 . .
C C11 0.24321(11) -0.0663(3) 0.48374(8) 0.0261(4) Uani d . . . 1 . .
C C12 0.18803(12) -0.2353(3) 0.49111(9) 0.0303(4) Uani d . . . 1 . .
H H12 0.211355 -0.376509 0.510365 0.036000 Uiso calc U . R 1 . .
C C13 0.10019(12) -0.1994(3) 0.47078(9) 0.0333(4) Uani d . . . 1 . .
H H13 0.063835 -0.314845 0.477085 0.040000 Uiso calc U . R 1 . .
C C14 0.06455(12) 0.0041(3) 0.44118(9) 0.0338(4) Uani d . . . 1 . .
H H14 0.004012 0.027876 0.427011 0.041000 Uiso calc U . R 1 . .
C C15 0.11800(12) 0.1725(3) 0.43244(9) 0.0313(4) Uani d . . . 1 . .
H H15 0.093996 0.311748 0.411905 0.038000 Uiso calc U . R 1 . .
C C16 0.20698(11) 0.1377(3) 0.45378(9) 0.0273(4) Uani d . . . 1 . .
H H16 0.243252 0.253939 0.447850 0.033000 Uiso calc U . R 1 . .
C C21 0.58210(10) 0.6914(3) 0.73605(9) 0.0225(4) Uani d . . . 1 . .
C C22 0.59039(11) 0.7070(3) 0.67094(9) 0.0264(4) Uani d . . . 1 . .
H H22 0.563138 0.598873 0.636037 0.032000 Uiso calc U . R 1 . .
C C23 0.63829(11) 0.8798(3) 0.65676(10) 0.0330(4) Uani d . . . 1 . .
H H23 0.643040 0.891172 0.612015 0.040000 Uiso calc U . R 1 . .
C C24 0.67945(11) 1.0367(3) 0.70830(11) 0.0360(5) Uani d . . . 1 . .
H H24 0.711896 1.155859 0.698651 0.043000 Uiso calc U . R 1 . .
C C25 0.67286(11) 1.0181(3) 0.77318(11) 0.0344(5) Uani d . . . 1 . .
H H25 0.702048 1.122773 0.808604 0.041000 Uiso calc U . R 1 . .
C C26 0.62398(11) 0.8478(3) 0.78729(9) 0.0285(4) Uani d . . . 1 . .
H H26 0.619058 0.837925 0.832007 0.034000 Uiso calc U . R 1 . .
C C31 0.36752(10) 0.6700(3) 0.75412(8) 0.0213(4) Uani d . . . 1 . .
C C32 0.39526(10) 0.8776(3) 0.78510(9) 0.0262(4) Uani d . . . 1 . .
H H32 0.421609 0.981497 0.763479 0.031000 Uiso calc U . R 1 . .
C C33 0.38478(11) 0.9345(3) 0.84755(9) 0.0312(4) Uani d . . . 1 . .
H H33 0.404297 1.076292 0.868555 0.037000 Uiso calc U . R 1 . .
C C34 0.34590(12) 0.7843(3) 0.87896(9) 0.0332(4) Uani d . . . 1 . .
H H34 0.339213 0.822075 0.921826 0.040000 Uiso calc U . R 1 . .
C C35 0.31665(11) 0.5781(3) 0.84767(9) 0.0308(4) Uani d . . . 1 . .
H H35 0.288908 0.475947 0.868678 0.037000 Uiso calc U . R 1 . .
C C36 0.32789(10) 0.5217(3) 0.78600(9) 0.0245(4) Uani d . . . 1 . .
H H36 0.308305 0.379758 0.765127 0.029000 Uiso calc U . R 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
N1 C5 . 1.346(2) ?
N1 C6 . 1.465(2) ?
N1 C7 . 1.471(2) ?
O1 C1 . 1.225(2) ?
C1 C2 . 1.453(2) ?
C1 H1 . 0.950000 ?
C2 C3 . 1.369(2) ?
C2 C11 . 1.485(2) ?
C3 C4 . 1.420(2) ?
C3 H3 . 0.950000 ?
C4 C5 . 1.361(2) ?
C4 H4 . 0.950000 ?
C5 H5 . 0.950000 ?
C6 C21 . 1.512(2) ?
C6 H6A . 0.990000 ?
C6 H6B . 0.990000 ?
C7 C31 . 1.512(2) ?
C7 H7A . 0.990000 ?
C7 H7B . 0.990000 ?
C11 C16 . 1.396(2) ?
C11 C12 . 1.400(2) ?
C12 C13 . 1.380(3) ?
C12 H12 . 0.950000 ?
C13 C14 . 1.389(3) ?
C13 H13 . 0.950000 ?
C14 C15 . 1.387(3) ?
C14 H14 . 0.950000 ?
C15 C16 . 1.396(3) ?
C15 H15 . 0.950000 ?
C16 H16 . 0.950000 ?
C21 C22 . 1.392(2) ?
C21 C26 . 1.392(2) ?
C22 C23 . 1.388(3) ?
C22 H22 . 0.950000 ?
C23 C24 . 1.395(3) ?
C23 H23 . 0.950000 ?
C24 C25 . 1.376(3) ?
C24 H24 . 0.950000 ?
C25 C26 . 1.387(3) ?
C25 H25 . 0.950000 ?
C26 H26 . 0.950000 ?
C31 C32 . 1.390(2) ?
C31 C36 . 1.390(2) ?
C32 C33 . 1.392(3) ?
C32 H32 . 0.950000 ?
C33 C34 . 1.383(3) ?
C33 H33 . 0.950000 ?
C34 C35 . 1.389(3) ?
C34 H34 . 0.950000 ?
C35 C36 . 1.382(2) ?
C35 H35 . 0.950000 ?
C36 H36 . 0.950000 ?

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
C5 N1 C6 . . 119.26(13) ?
C5 N1 C7 . . 122.21(14) ?
C6 N1 C7 . . 116.92(13) ?
O1 C1 C2 . . 126.04(18) ?
O1 C1 H1 . . 117.000000 ?
C2 C1 H1 . . 117.000000 ?
C3 C2 C1 . . 116.14(16) ?
C3 C2 C11 . . 123.58(16) ?
C1 C2 C11 . . 120.19(16) ?
C2 C3 C4 . . 129.42(17) ?
C2 C3 H3 . . 115.300000 ?
C4 C3 H3 . . 115.300000 ?
C5 C4 C3 . . 118.88(16) ?
C5 C4 H4 . . 120.600000 ?
C3 C4 H4 . . 120.600000 ?
N1 C5 C4 . . 129.86(16) ?
N1 C5 H5 . . 115.100000 ?
C4 C5 H5 . . 115.100000 ?
N1 C6 C21 . . 114.48(13) ?
N1 C6 H6A . . 108.600000 ?
C21 C6 H6A . . 108.600000 ?
N1 C6 H6B . . 108.600000 ?
C21 C6 H6B . . 108.600000 ?
H6A C6 H6B . . 107.600000 ?
N1 C7 C31 . . 112.15(13) ?
N1 C7 H7A . . 109.200000 ?
C31 C7 H7A . . 109.200000 ?
N1 C7 H7B . . 109.200000 ?
C31 C7 H7B . . 109.200000 ?
H7A C7 H7B . . 107.900000 ?
C16 C11 C12 . . 118.36(17) ?
C16 C11 C2 . . 121.70(15) ?
C12 C11 C2 . . 119.93(16) ?
C13 C12 C11 . . 120.87(18) ?
C13 C12 H12 . . 119.600000 ?
C11 C12 H12 . . 119.600000 ?
C12 C13 C14 . . 120.49(17) ?
C12 C13 H13 . . 119.800000 ?
C14 C13 H13 . . 119.800000 ?
C15 C14 C13 . . 119.52(17) ?
C15 C14 H14 . . 120.200000 ?
C13 C14 H14 . . 120.200000 ?
C14 C15 C16 . . 120.09(18) ?
C14 C15 H15 . . 120.000000 ?
C16 C15 H15 . . 120.000000 ?
C15 C16 C11 . . 120.65(16) ?
C15 C16 H16 . . 119.700000 ?
C11 C16 H16 . . 119.700000 ?
C22 C21 C26 . . 119.30(16) ?
C22 C21 C6 . . 121.23(15) ?
C26 C21 C6 . . 119.33(15) ?
C23 C22 C21 . . 120.31(17) ?
C23 C22 H22 . . 119.800000 ?
C21 C22 H22 . . 119.800000 ?
C22 C23 C24 . . 119.92(18) ?
C22 C23 H23 . . 120.000000 ?
C24 C23 H23 . . 120.000000 ?
C25 C24 C23 . . 119.72(17) ?
C25 C24 H24 . . 120.100000 ?
C23 C24 H24 . . 120.100000 ?
C24 C25 C26 . . 120.58(18) ?
C24 C25 H25 . . 119.700000 ?
C26 C25 H25 . . 119.700000 ?
C25 C26 C21 . . 120.14(17) ?
C25 C26 H26 . . 119.900000 ?
C21 C26 H26 . . 119.900000 ?
C32 C31 C36 . . 118.85(16) ?
C32 C31 C7 . . 121.08(15) ?
C36 C31 C7 . . 120.07(15) ?
C31 C32 C33 . . 120.57(17) ?
C31 C32 H32 . . 119.700000 ?
C33 C32 H32 . . 119.700000 ?
C34 C33 C32 . . 119.90(17) ?
C34 C33 H33 . . 120.000000 ?
C32 C33 H33 . . 120.000000 ?
C33 C34 C35 . . 119.84(17) ?
C33 C34 H34 . . 120.100000 ?
C35 C34 H34 . . 120.100000 ?
C36 C35 C34 . . 120.01(17) ?
C36 C35 H35 . . 120.000000 ?
C34 C35 H35 . . 120.000000 ?
C35 C36 C31 . . 120.80(17) ?
C35 C36 H36 . . 119.600000 ?
C31 C36 H36 . . 119.600000 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C3 . . . . 177.68(18) ?
O1 C1 C2 C11 . . . . 1.0(3) ?
C1 C2 C3 C4 . . . . -176.59(17) ?
C11 C2 C3 C4 . . . . 0.0(3) ?
C2 C3 C4 C5 . . . . 167.80(17) ?
C6 N1 C5 C4 . . . . -176.42(17) ?
C7 N1 C5 C4 . . . . -11.3(3) ?
C3 C4 C5 N1 . . . . -176.80(16) ?
C5 N1 C6 C21 . . . . 94.58(17) ?
C7 N1 C6 C21 . . . . -71.30(18) ?
C5 N1 C7 C31 . . . . 145.22(15) ?
C6 N1 C7 C31 . . . . -49.35(19) ?
C3 C2 C11 C16 . . . . 60.2(2) ?
C1 C2 C11 C16 . . . . -123.35(18) ?
C3 C2 C11 C12 . . . . -119.44(19) ?
C1 C2 C11 C12 . . . . 57.0(2) ?
C16 C11 C12 C13 . . . . -1.5(2) ?
C2 C11 C12 C13 . . . . 178.18(16) ?
C11 C12 C13 C14 . . . . 1.3(3) ?
C12 C13 C14 C15 . . . . -0.3(3) ?
C13 C14 C15 C16 . . . . -0.5(3) ?
C14 C15 C16 C11 . . . . 0.3(3) ?
C12 C11 C16 C15 . . . . 0.7(2) ?
C2 C11 C16 C15 . . . . -179.00(16) ?
N1 C6 C21 C22 . . . . -44.1(2) ?
N1 C6 C21 C26 . . . . 140.17(15) ?
C26 C21 C22 C23 . . . . -1.5(2) ?
C6 C21 C22 C23 . . . . -177.18(15) ?
C21 C22 C23 C24 . . . . 1.0(3) ?
C22 C23 C24 C25 . . . . 0.5(3) ?
C23 C24 C25 C26 . . . . -1.5(3) ?
C24 C25 C26 C21 . . . . 1.0(3) ?
C22 C21 C26 C25 . . . . 0.5(2) ?
C6 C21 C26 C25 . . . . 176.26(15) ?
N1 C7 C31 C32 . . . . 103.90(18) ?
N1 C7 C31 C36 . . . . -75.66(19) ?
C36 C31 C32 C33 . . . . 1.0(2) ?
C7 C31 C32 C33 . . . . -178.57(15) ?
C31 C32 C33 C34 . . . . -0.5(3) ?
C32 C33 C34 C35 . . . . -0.7(3) ?
C33 C34 C35 C36 . . . . 1.2(3) ?
C34 C35 C36 C31 . . . . -0.7(3) ?
C32 C31 C36 C35 . . . . -0.4(2) ?
C7 C31 C36 C35 . . . . 179.14(15) ?



#=============================================================================
#  end of cif data for "glo10557"  (compound 2a)
#=============================================================================
#=============================================================================
#  end of cif file
#=============================================================================

