# Electronic Supplementary Material (ESI) 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_CH_B1_0075
_database_code_depnum_ccdc_archive 'CCDC 2352884'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2024-05-03 deposited with the CCDC.	2024-06-26 downloaded from the CCDC.
;
#===============================================================================
_audit_creation_method           SHELXL-2019/2

#-------------------------------------------------------------------------------
# Inserted by local software: cifUpdate ver. 3.1  (Andrew D. Bond, March 2019)
#-------------------------------------------------------------------------------
_cambridge_user_name             'Fergal Hanna'
_cambridge_user_crsid            feh27
_cambridge_supervisor_name       'Chris Hunter'
_cambridge_supervisor_crsid      ch664
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_crsid adb29
_cambridge_sample_id             FHBK4-140
_cambridge_data_id               CH_B1_0075

_database_code_CSD               ?
#-------------------------------------------------------------------------------

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H23 N3 O3'
_chemical_formula_sum            'C18 H23 N3 O3'
_chemical_formula_weight         329.39

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   17.6378(9)
_cell_length_b                   4.1739(3)
_cell_length_c                   24.0146(11)
_cell_angle_alpha                90
_cell_angle_beta                 106.817(3)
_cell_angle_gamma                90
_cell_volume                     1692.31(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    2011
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      65.32

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.724
_shelx_estimated_absorpt_T_min   0.823
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5982
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-III'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22417
_diffrn_reflns_av_unetI/netI     0.0847
_diffrn_reflns_av_R_equivalents  0.1147
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.617
_diffrn_reflns_theta_max         66.608
_diffrn_reflns_theta_full        66.608
_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             2963
_reflns_number_gt                2018
_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       'APEX4 (Bruker, 2021)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_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)+(0.0324P)²+0.6220P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0031(5)
_refine_ls_number_reflns         2963
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.1349
_refine_ls_wR_factor_gt          0.1164
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.054

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 0.33368(12) -0.1421(6) 0.27566(8) 0.0619(6) Uani 1 1 d . . . . .
O2 O 0.22591(12) 0.1033(6) 0.22966(7) 0.0690(7) Uani 1 1 d . . . . .
O3 O 0.42576(9) 0.2639(4) 0.51740(6) 0.0356(4) Uani 1 1 d . . . . .
N1 N 0.23603(11) 0.4125(5) 0.48749(8) 0.0360(5) Uani 1 1 d . . . . .
H1 H 0.2711(15) 0.349(6) 0.5209(11) 0.038(7) Uiso 1 1 d . . . . .
N2 N 0.27589(13) 0.0244(6) 0.27501(8) 0.0470(6) Uani 1 1 d . . . . .
N3 N 0.36929(11) 0.2916(6) 0.59343(8) 0.0399(5) Uani 1 1 d . . . . .
C1 C 0.24624(13) 0.3207(6) 0.43617(9) 0.0331(6) Uani 1 1 d . . . . .
C2 C 0.19176(13) 0.4112(6) 0.38297(10) 0.0377(6) Uani 1 1 d . . . . .
H2A H 0.147431 0.539699 0.383282 0.045 Uiso 1 1 calc R U . . .
C3 C 0.20166(14) 0.3165(7) 0.33042(10) 0.0411(6) Uani 1 1 d . . . . .
H3A H 0.164510 0.379410 0.294908 0.049 Uiso 1 1 calc R U . . .
C4 C 0.26600(13) 0.1296(7) 0.32996(9) 0.0378(6) Uani 1 1 d . . . . .
C5 C 0.32091(13) 0.0363(6) 0.38173(10) 0.0358(6) Uani 1 1 d . . . . .
H5A H 0.364795 -0.092650 0.380544 0.043 Uiso 1 1 calc R U . . .
C6 C 0.31242(13) 0.1283(6) 0.43437(9) 0.0324(5) Uani 1 1 d . . . . .
C7 C 0.37115(13) 0.0126(6) 0.48933(9) 0.0343(6) Uani 1 1 d . . . . .
H7A H 0.342368 -0.065401 0.516481 0.041 Uiso 1 1 calc R U . . .
H7B H 0.401450 -0.169410 0.480116 0.041 Uiso 1 1 calc R U . . .
C8 C 0.16745(13) 0.5918(6) 0.49216(10) 0.0373(6) Uani 1 1 d . . . . .
H8A H 0.118855 0.466208 0.474384 0.045 Uiso 1 1 calc R U . . .
H8B H 0.163670 0.795037 0.470263 0.045 Uiso 1 1 calc R U . . .
C9 C 0.17233(13) 0.6654(6) 0.55468(10) 0.0374(6) Uani 1 1 d . . . . .
H9A H 0.216682 0.815526 0.570903 0.045 Uiso 1 1 calc R U . . .
H9B H 0.183336 0.465368 0.577780 0.045 Uiso 1 1 calc R U . . .
C10 C 0.09564(13) 0.8130(6) 0.55971(10) 0.0372(6) Uani 1 1 d . . . . .
H10A H 0.085352 1.012761 0.536496 0.045 Uiso 1 1 calc R U . . .
H10B H 0.051591 0.663296 0.542401 0.045 Uiso 1 1 calc R U . . .
C11 C 0.09514(14) 0.8902(6) 0.62129(10) 0.0378(6) Uani 1 1 d . . . . .
H11A H 0.136680 1.051561 0.637887 0.045 Uiso 1 1 calc R U . . .
H11B H 0.108447 0.694004 0.645295 0.045 Uiso 1 1 calc R U . . .
C12 C 0.01590(14) 1.0178(7) 0.62475(10) 0.0415(6) Uani 1 1 d . . . . .
H12A H 0.003024 1.215400 0.601079 0.050 Uiso 1 1 calc R U . . .
H12B H -0.025672 0.857641 0.607534 0.050 Uiso 1 1 calc R U . . .
C13 C 0.01408(16) 1.0917(8) 0.68588(11) 0.0515(7) Uani 1 1 d . . . . .
H13A H -0.039086 1.164003 0.685080 0.077 Uiso 1 1 calc R U . . .
H13B H 0.052587 1.260669 0.702398 0.077 Uiso 1 1 calc R U . . .
H13C H 0.027549 0.898250 0.709853 0.077 Uiso 1 1 calc R U . . .
C14 C 0.42958(13) 0.3552(6) 0.57265(9) 0.0326(5) Uani 1 1 d . . . . .
C15 C 0.49633(14) 0.5228(6) 0.60281(10) 0.0389(6) Uani 1 1 d . . . . .
H15A H 0.537553 0.566723 0.585746 0.047 Uiso 1 1 calc R U . . .
C16 C 0.50142(15) 0.6240(7) 0.65815(11) 0.0451(7) Uani 1 1 d . . . . .
H16A H 0.546608 0.739123 0.680211 0.054 Uiso 1 1 calc R U . . .
C17 C 0.43987(15) 0.5565(7) 0.68157(10) 0.0461(7) Uani 1 1 d . . . . .
H17A H 0.442336 0.621760 0.719947 0.055 Uiso 1 1 calc R U . . .
C18 C 0.37579(15) 0.3941(7) 0.64803(10) 0.0461(7) Uani 1 1 d . . . . .
H18A H 0.333390 0.350457 0.663900 0.055 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 N2 1.230(3) . ?
O2 N2 1.231(3) . ?
O3 C14 1.363(3) . ?
O3 C7 1.452(3) . ?
N1 C1 1.351(3) . ?
N1 C8 1.454(3) . ?
N1 H1 0.90(3) . ?
N2 C4 1.448(3) . ?
N3 C14 1.326(3) . ?
N3 C18 1.352(3) . ?
C1 C2 1.410(3) . ?
C1 C6 1.428(3) . ?
C2 C3 1.381(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.380(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.392(3) . ?
C5 C6 1.370(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.502(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.510(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.523(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.516(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.520(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.510(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.381(3) . ?
C15 C16 1.373(3) . ?
C15 H15A 0.9500 . ?
C16 C17 1.388(4) . ?
C16 H16A 0.9500 . ?
C17 C18 1.363(4) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?

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
C14 O3 C7 119.55(18) . . ?
C1 N1 C8 123.33(19) . . ?
C1 N1 H1 119.4(16) . . ?
C8 N1 H1 117.1(16) . . ?
O1 N2 O2 122.7(2) . . ?
O1 N2 C4 118.5(2) . . ?
O2 N2 C4 118.7(2) . . ?
C14 N3 C18 116.7(2) . . ?
N1 C1 C2 121.0(2) . . ?
N1 C1 C6 120.9(2) . . ?
C2 C1 C6 118.2(2) . . ?
C3 C2 C1 121.2(2) . . ?
C3 C2 H2A 119.4 . . ?
C1 C2 H2A 119.4 . . ?
C4 C3 C2 119.4(2) . . ?
C4 C3 H3A 120.3 . . ?
C2 C3 H3A 120.3 . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 N2 119.7(2) . . ?
C5 C4 N2 119.5(2) . . ?
C6 C5 C4 120.8(2) . . ?
C6 C5 H5A 119.6 . . ?
C4 C5 H5A 119.6 . . ?
C5 C6 C1 119.6(2) . . ?
C5 C6 C7 119.3(2) . . ?
C1 C6 C7 121.1(2) . . ?
O3 C7 C6 111.83(19) . . ?
O3 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
O3 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
N1 C8 C9 111.83(18) . . ?
N1 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 C10 111.39(19) . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C9 114.80(19) . . ?
C11 C10 H10A 108.6 . . ?
C9 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.5 . . ?
C10 C11 C12 113.12(19) . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 113.8(2) . . ?
C13 C12 H12A 108.8 . . ?
C11 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 O3 119.4(2) . . ?
N3 C14 C15 124.0(2) . . ?
O3 C14 C15 116.5(2) . . ?
C16 C15 C14 118.1(2) . . ?
C16 C15 H15A 121.0 . . ?
C14 C15 H15A 121.0 . . ?
C15 C16 C17 119.3(2) . . ?
C15 C16 H16A 120.3 . . ?
C17 C16 H16A 120.3 . . ?
C18 C17 C16 118.3(2) . . ?
C18 C17 H17A 120.9 . . ?
C16 C17 H17A 120.9 . . ?
N3 C18 C17 123.6(2) . . ?
N3 C18 H18A 118.2 . . ?
C17 C18 H18A 118.2 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C2 3.6(4) . . . . ?
C8 N1 C1 C6 -176.2(2) . . . . ?
N1 C1 C2 C3 -179.6(2) . . . . ?
C6 C1 C2 C3 0.2(4) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C2 C3 C4 N2 178.8(2) . . . . ?
O1 N2 C4 C3 -180.0(3) . . . . ?
O2 N2 C4 C3 -0.5(4) . . . . ?
O1 N2 C4 C5 -1.0(4) . . . . ?
O2 N2 C4 C5 178.5(2) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
N2 C4 C5 C6 -179.0(2) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C4 C5 C6 C7 177.7(2) . . . . ?
N1 C1 C6 C5 179.4(2) . . . . ?
C2 C1 C6 C5 -0.4(3) . . . . ?
N1 C1 C6 C7 2.1(3) . . . . ?
C2 C1 C6 C7 -177.7(2) . . . . ?
C14 O3 C7 C6 120.5(2) . . . . ?
C5 C6 C7 O3 105.3(2) . . . . ?
C1 C6 C7 O3 -77.4(3) . . . . ?
C1 N1 C8 C9 -179.2(2) . . . . ?
N1 C8 C9 C10 -172.4(2) . . . . ?
C8 C9 C10 C11 179.2(2) . . . . ?
C9 C10 C11 C12 -176.4(2) . . . . ?
C10 C11 C12 C13 179.2(2) . . . . ?
C18 N3 C14 O3 -178.6(2) . . . . ?
C18 N3 C14 C15 -1.4(4) . . . . ?
C7 O3 C14 N3 -20.6(3) . . . . ?
C7 O3 C14 C15 161.9(2) . . . . ?
N3 C14 C15 C16 1.4(4) . . . . ?
O3 C14 C15 C16 178.7(2) . . . . ?
C14 C15 C16 C17 -0.3(4) . . . . ?
C15 C16 C17 C18 -0.8(4) . . . . ?
C14 N3 C18 C17 0.2(4) . . . . ?
C16 C17 C18 N3 0.8(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 N3 0.90(3) 2.08(3) 2.965(3) 166(2) . yes



