# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_nb1_0m
_database_code_depnum_ccdc_archive 'CCDC 2237074'
_audit_update_record             
;
2023-01-19 deposited with the CCDC.	2023-10-30 downloaded from the CCDC.
;
_audit_creation_date             2022-11-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H27 N3 O3'
_chemical_formula_sum            'C28 H27 N3 O3'
_chemical_formula_weight         453.52
_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'
O O 0.0106 0.0060 '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                   8.6308(9)
_cell_length_b                   9.4001(9)
_cell_length_c                   28.739(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.326(3)
_cell_angle_gamma                90
_cell_volume                     2307.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4117
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.900
_cell_measurement_theta_min      2.383
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6123
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0821 before and 0.0570 after correction. The Ratio of minimum to maximum transmission is 0.8214. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            16976
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.400
_diffrn_reflns_theta_min         2.282
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2940
_reflns_number_total             4654
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4654
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0533
_refine_ls_restrained_S_all      1.059
_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)+(0.0343P)²+1.3739P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1281
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C4(H4A,H4B), C3(H3A,H3B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C28(H28), C24(H24), C25(H25), C26(H26), C18(H18), C27(H27), C15(H15),
 C20(H20), C19(H19)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C7(H7A,H7B,H7C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O2 O 0.59906(17) 0.57224(17) 0.55148(6) 0.0307(4) Uani 1 1 d . . . . .
O3 O 0.11108(18) 0.66617(19) 0.58568(6) 0.0358(4) Uani 1 1 d . . . . .
O1 O 0.82951(19) 0.3687(2) 0.73168(6) 0.0391(4) Uani 1 1 d . . . . .
N3 N 0.3474(2) 0.6351(2) 0.55951(7) 0.0276(5) Uani 1 1 d . . . . .
N1 N 0.8297(2) 0.1564(2) 0.69352(7) 0.0332(5) Uani 1 1 d . . . . .
C22 C 0.4754(2) 0.3320(2) 0.60827(7) 0.0222(5) Uani 1 1 d . . . . .
C23 C 0.3304(2) 0.2595(2) 0.58597(8) 0.0235(5) Uani 1 1 d . . . . .
C21 C 0.6142(2) 0.2699(2) 0.62222(8) 0.0227(5) Uani 1 1 d . . . . .
C8 C 0.4897(3) 0.5703(2) 0.57375(8) 0.0254(5) Uani 1 1 d . . . . .
C10 C 0.6352(2) 0.5034(2) 0.65500(8) 0.0259(5) Uani 1 1 d . . . . .
H10A H 0.693927 0.589658 0.648251 0.031 Uiso 1 1 calc R . . . .
H10B H 0.611763 0.509559 0.687654 0.031 Uiso 1 1 calc R . . . .
C9 C 0.4821(2) 0.4912(2) 0.62005(8) 0.0230(5) Uani 1 1 d . . . . .
C11 C 0.7321(2) 0.3688(2) 0.64872(8) 0.0253(5) Uani 1 1 d . . . . .
C17 C 0.6670(3) 0.1233(2) 0.61718(8) 0.0274(5) Uani 1 1 d . . . . .
C5 C 0.3287(2) 0.5502(2) 0.63558(8) 0.0251(5) Uani 1 1 d . . . . .
H5 H 0.264389 0.468801 0.644491 0.030 Uiso 1 1 calc R . . . .
C6 C 0.2441(3) 0.6204(2) 0.59189(8) 0.0272(5) Uani 1 1 d . . . . .
C28 C 0.2548(3) 0.2936(3) 0.54130(8) 0.0285(5) Uani 1 1 d . . . . .
H28 H 0.295723 0.366436 0.523665 0.034 Uiso 1 1 calc R . . . .
C4 C 0.3465(3) 0.6605(2) 0.67516(8) 0.0283(5) Uani 1 1 d . . . . .
H4A H 0.406793 0.617200 0.703578 0.034 Uiso 1 1 calc R . . . .
H4B H 0.241195 0.684225 0.682692 0.034 Uiso 1 1 calc R . . . .
C12 C 0.7983(3) 0.2998(3) 0.69528(9) 0.0298(6) Uani 1 1 d . . . . .
C24 C 0.2683(3) 0.1518(2) 0.61111(8) 0.0280(5) Uani 1 1 d . . . . .
H24 H 0.317818 0.128345 0.641849 0.034 Uiso 1 1 calc R . . . .
C3 C 0.4279(3) 0.7984(2) 0.66401(8) 0.0291(6) Uani 1 1 d . . . . .
H3A H 0.362480 0.847463 0.637681 0.035 Uiso 1 1 calc R . . . .
H3B H 0.529360 0.774845 0.653631 0.035 Uiso 1 1 calc R . . . .
C25 C 0.1352(3) 0.0789(3) 0.59168(9) 0.0330(6) Uani 1 1 d . . . . .
H25 H 0.095651 0.003756 0.608710 0.040 Uiso 1 1 calc R . . . .
C13 C 0.8734(3) 0.3998(3) 0.62290(9) 0.0311(6) Uani 1 1 d . . . . .
H13A H 0.925197 0.310145 0.616996 0.047 Uiso 1 1 calc GR . . . .
H13B H 0.947575 0.461763 0.642408 0.047 Uiso 1 1 calc GR . . . .
H13C H 0.836989 0.446991 0.592904 0.047 Uiso 1 1 calc GR . . . .
C26 C 0.0600(3) 0.1149(3) 0.54776(9) 0.0362(6) Uani 1 1 d . . . . .
H26 H -0.033057 0.066519 0.534905 0.043 Uiso 1 1 calc R . . . .
C16 C 0.7811(3) 0.0720(3) 0.65320(9) 0.0317(6) Uani 1 1 d . . . . .
C7 C 0.3070(3) 0.7082(3) 0.51461(9) 0.0371(6) Uani 1 1 d . . . . .
H7A H 0.288587 0.809207 0.520272 0.056 Uiso 1 1 calc GR . . . .
H7B H 0.212003 0.665914 0.497289 0.056 Uiso 1 1 calc GR . . . .
H7C H 0.393356 0.698663 0.496119 0.056 Uiso 1 1 calc GR . . . .
N2 N 0.6426(3) 0.7842(3) 0.77533(9) 0.0624(8) Uani 1 1 d . . . . .
C2 C 0.4571(3) 0.8996(3) 0.70617(8) 0.0352(6) Uani 1 1 d . . . . .
H2A H 0.503937 0.988992 0.696460 0.042 Uiso 1 1 calc R . . . .
H2B H 0.356017 0.923351 0.716722 0.042 Uiso 1 1 calc R . . . .
C18 C 0.6187(3) 0.0383(2) 0.57828(9) 0.0317(6) Uani 1 1 d . . . . .
H18 H 0.540379 0.072450 0.554210 0.038 Uiso 1 1 calc R . . . .
C27 C 0.1194(3) 0.2214(3) 0.52228(9) 0.0342(6) Uani 1 1 d . . . . .
H27 H 0.067940 0.245299 0.491797 0.041 Uiso 1 1 calc R . . . .
C15 C 0.8419(3) -0.0649(3) 0.64903(10) 0.0396(7) Uani 1 1 d . . . . .
H15 H 0.916240 -0.102401 0.673581 0.048 Uiso 1 1 calc R . . . .
C20 C 0.7942(3) -0.1456(3) 0.60925(11) 0.0431(7) Uani 1 1 d . . . . .
H20 H 0.838980 -0.236835 0.606258 0.052 Uiso 1 1 calc R . . . .
C1 C 0.5619(4) 0.8361(3) 0.74525(10) 0.0423(7) Uani 1 1 d . . . . .
C19 C 0.6825(3) -0.0954(3) 0.57394(10) 0.0410(7) Uani 1 1 d . . . . .
H19 H 0.649666 -0.151875 0.546897 0.049 Uiso 1 1 calc R . . . .
C14 C 0.9287(3) 0.0928(3) 0.73400(10) 0.0486(8) Uani 1 1 d . . . . .
H14A H 1.030315 0.066958 0.725049 0.073 Uiso 1 1 calc GR . . . .
H14B H 0.877554 0.007396 0.744111 0.073 Uiso 1 1 calc GR . . . .
H14C H 0.944216 0.161557 0.759890 0.073 Uiso 1 1 calc GR . . . .


_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
O2 C8 1.215(2) . ?
O3 C6 1.214(3) . ?
O1 C12 1.227(3) . ?
N3 C8 1.379(3) . ?
N3 C6 1.386(3) . ?
N3 C7 1.459(3) . ?
N1 C12 1.378(3) . ?
N1 C16 1.417(3) . ?
N1 C14 1.467(3) . ?
C22 C23 1.485(3) . ?
C22 C21 1.341(3) . ?
C22 C9 1.534(3) . ?
C23 C28 1.391(3) . ?
C23 C24 1.395(3) . ?
C21 C11 1.502(3) . ?
C21 C17 1.465(3) . ?
C8 C9 1.534(3) . ?
C10 C9 1.544(3) . ?
C10 C11 1.541(3) . ?
C9 C5 1.558(3) . ?
C11 C12 1.522(3) . ?
C11 C13 1.544(3) . ?
C17 C16 1.407(3) . ?
C17 C18 1.388(3) . ?
C5 C6 1.510(3) . ?
C5 C4 1.531(3) . ?
C28 C27 1.393(3) . ?
C4 C3 1.531(3) . ?
C24 C25 1.385(3) . ?
C3 C2 1.532(3) . ?
C25 C26 1.376(3) . ?
C26 C27 1.382(3) . ?
C16 C15 1.401(3) . ?
N2 C1 1.138(4) . ?
C2 C1 1.463(4) . ?
C18 C19 1.385(3) . ?
C15 C20 1.384(4) . ?
C20 C19 1.378(4) . ?

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
C8 N3 C6 112.89(19) . . ?
C8 N3 C7 123.99(19) . . ?
C6 N3 C7 123.10(19) . . ?
C12 N1 C16 122.8(2) . . ?
C12 N1 C14 117.7(2) . . ?
C16 N1 C14 119.3(2) . . ?
C23 C22 C9 123.02(19) . . ?
C21 C22 C23 126.2(2) . . ?
C21 C22 C9 110.80(19) . . ?
C28 C23 C22 123.1(2) . . ?
C28 C23 C24 118.7(2) . . ?
C24 C23 C22 118.2(2) . . ?
C22 C21 C11 113.1(2) . . ?
C22 C21 C17 131.1(2) . . ?
C17 C21 C11 115.78(19) . . ?
O2 C8 N3 124.3(2) . . ?
O2 C8 C9 126.8(2) . . ?
N3 C8 C9 108.85(18) . . ?
C11 C10 C9 106.89(18) . . ?
C22 C9 C8 106.64(18) . . ?
C22 C9 C10 102.56(17) . . ?
C22 C9 C5 113.82(17) . . ?
C8 C9 C10 112.81(18) . . ?
C8 C9 C5 102.78(17) . . ?
C10 C9 C5 118.02(18) . . ?
C21 C11 C10 103.21(17) . . ?
C21 C11 C12 108.83(19) . . ?
C21 C11 C13 113.40(18) . . ?
C10 C11 C13 112.40(18) . . ?
C12 C11 C10 112.83(19) . . ?
C12 C11 C13 106.29(18) . . ?
C16 C17 C21 116.4(2) . . ?
C18 C17 C21 124.0(2) . . ?
C18 C17 C16 119.5(2) . . ?
C6 C5 C9 104.25(17) . . ?
C6 C5 C4 107.80(19) . . ?
C4 C5 C9 117.12(18) . . ?
O3 C6 N3 123.5(2) . . ?
O3 C6 C5 127.6(2) . . ?
N3 C6 C5 108.71(18) . . ?
C23 C28 C27 120.3(2) . . ?
C5 C4 C3 114.72(18) . . ?
O1 C12 N1 121.9(2) . . ?
O1 C12 C11 122.2(2) . . ?
N1 C12 C11 115.8(2) . . ?
C25 C24 C23 120.6(2) . . ?
C4 C3 C2 112.83(19) . . ?
C26 C25 C24 120.1(2) . . ?
C25 C26 C27 120.2(2) . . ?
C17 C16 N1 120.2(2) . . ?
C15 C16 N1 120.9(2) . . ?
C15 C16 C17 118.9(2) . . ?
C1 C2 C3 111.5(2) . . ?
C19 C18 C17 121.2(3) . . ?
C26 C27 C28 120.0(2) . . ?
C20 C15 C16 120.2(3) . . ?
C19 C20 C15 120.9(2) . . ?
N2 C1 C2 178.7(3) . . ?
C20 C19 C18 119.3(3) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
