# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_testm1
_database_code_depnum_ccdc_archive 'CCDC 2084176'
loop_
_audit_author_name
_audit_author_address
'John Bower'
;University of Liverpool
United Kingdom
;
_audit_update_record             
;
2022-04-05 deposited with the CCDC.	2022-09-02 downloaded from the CCDC.
;
_audit_creation_date             2017-10-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H27 N O2'
_chemical_formula_sum            'C20 H27 N O2'
_chemical_formula_weight         313.42
_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                   6.31820(10)
_cell_length_b                   39.6141(8)
_cell_length_c                   7.7124(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.7690(10)
_cell_angle_gamma                90
_cell_volume                     1792.68(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5375
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      2.89
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0707 before and 0.0491 after correction. The Ratio of minimum to maximum transmission is 0.8138. 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    1.161
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.235
_exptl_crystal_size_min          0.198
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       52
_diffrn_reflns_limit_k_min       -52
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            32572
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.923
_diffrn_reflns_theta_min         2.056
_diffrn_ambient_temperature      200(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3315
_reflns_number_total             4287
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker Apex suite'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.230
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         4287
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0550
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0349P)²+0.8402P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1172
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15), C18(H18)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C),
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_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
O1 O 0.72031(18) 0.31102(3) 0.84250(14) 0.0255(2) Uani 1 1 d . . . . .
O2 O 0.5229(2) 0.40981(3) 0.59643(17) 0.0418(3) Uani 1 1 d . . . . .
N1 N 0.8229(2) 0.42560(3) 0.85386(19) 0.0289(3) Uani 1 1 d . . . . .
C1 C 0.4245(3) 0.33144(4) 0.3513(2) 0.0277(3) Uani 1 1 d . . . . .
H1 H 0.417840 0.354329 0.385743 0.033 Uiso 1 1 calc R . . . .
C2 C 0.2361(3) 0.31679(4) 0.2161(2) 0.0320(4) Uani 1 1 d . . . . .
H2 H 0.102331 0.329817 0.157083 0.038 Uiso 1 1 calc R . . . .
C3 C 0.2413(3) 0.28342(4) 0.1666(2) 0.0325(4) Uani 1 1 d . . . . .
H3 H 0.111158 0.273442 0.074735 0.039 Uiso 1 1 calc R . . . .
C4 C 0.4357(3) 0.26467(4) 0.2510(2) 0.0324(4) Uani 1 1 d . . . . .
H4 H 0.440264 0.241678 0.217522 0.039 Uiso 1 1 calc R . . . .
C5 C 0.6256(3) 0.27942(4) 0.3853(2) 0.0277(4) Uani 1 1 d . . . . .
H5 H 0.759357 0.266296 0.442709 0.033 Uiso 1 1 calc R . . . .
C6 C 0.6239(3) 0.31288(4) 0.43721(19) 0.0221(3) Uani 1 1 d . . . . .
C7 C 0.8279(3) 0.33009(4) 0.5889(2) 0.0243(3) Uani 1 1 d . . . . .
C8 C 0.8974(3) 0.36195(4) 0.5101(2) 0.0332(4) Uani 1 1 d . . . . .
H8A H 0.947957 0.355685 0.408694 0.050 Uiso 1 1 calc GR . . . .
H8B H 1.022048 0.373294 0.609244 0.050 Uiso 1 1 calc GR . . . .
H8C H 0.766519 0.377238 0.461949 0.050 Uiso 1 1 calc GR . . . .
C9 C 1.0369(3) 0.30683(5) 0.6624(2) 0.0347(4) Uani 1 1 d . . . . .
H9A H 0.997676 0.286438 0.715992 0.052 Uiso 1 1 calc GR . . . .
H9B H 1.161800 0.318674 0.758826 0.052 Uiso 1 1 calc GR . . . .
H9C H 1.084508 0.300541 0.559492 0.052 Uiso 1 1 calc GR . . . .
C10 C 0.7509(2) 0.33877(4) 0.7466(2) 0.0222(3) Uani 1 1 d . . . . .
C11 C 0.6931(3) 0.36700(4) 0.8178(2) 0.0237(3) Uani 1 1 d . . . . .
C12 C 0.6237(3) 0.35608(4) 0.9664(2) 0.0281(4) Uani 1 1 d . . . . .
H12 H 0.574538 0.370085 1.044186 0.034 Uiso 1 1 calc R . . . .
C13 C 0.6416(3) 0.32257(4) 0.9742(2) 0.0280(4) Uani 1 1 d . . . . .
H13 H 0.604678 0.308663 1.059307 0.034 Uiso 1 1 calc R . . . .
C14 C 0.6744(3) 0.40245(4) 0.7461(2) 0.0273(3) Uani 1 1 d . . . . .
C15 C 1.0087(3) 0.41695(4) 1.0326(2) 0.0345(4) Uani 1 1 d . . . . .
H15 H 1.002629 0.392004 1.050162 0.041 Uiso 1 1 calc R . . . .
C16 C 0.9757(4) 0.43383(6) 1.1974(3) 0.0487(5) Uani 1 1 d . . . . .
H16A H 0.983374 0.458386 1.185662 0.073 Uiso 1 1 calc GR . . . .
H16B H 1.095848 0.426422 1.313534 0.073 Uiso 1 1 calc GR . . . .
H16C H 0.826549 0.427570 1.199393 0.073 Uiso 1 1 calc GR . . . .
C17 C 1.2416(3) 0.42505(6) 1.0268(3) 0.0531(6) Uani 1 1 d . . . . .
H17A H 1.258074 0.413655 0.919721 0.080 Uiso 1 1 calc GR . . . .
H17B H 1.361036 0.417208 1.142282 0.080 Uiso 1 1 calc GR . . . .
H17C H 1.255630 0.449493 1.014727 0.080 Uiso 1 1 calc GR . . . .
C18 C 0.8057(3) 0.46109(4) 0.7907(3) 0.0357(4) Uani 1 1 d . . . . .
H18 H 0.928737 0.473745 0.889921 0.043 Uiso 1 1 calc R . . . .
C19 C 0.5824(4) 0.47731(5) 0.7758(3) 0.0527(6) Uani 1 1 d . . . . .
H19A H 0.456272 0.466091 0.677369 0.079 Uiso 1 1 calc GR . . . .
H19B H 0.584655 0.501288 0.745248 0.079 Uiso 1 1 calc GR . . . .
H19C H 0.561969 0.475043 0.895159 0.079 Uiso 1 1 calc GR . . . .
C20 C 0.8543(4) 0.46475(6) 0.6125(3) 0.0537(6) Uani 1 1 d . . . . .
H20A H 1.000893 0.454156 0.629830 0.081 Uiso 1 1 calc GR . . . .
H20B H 0.860138 0.488753 0.583865 0.081 Uiso 1 1 calc GR . . . .
H20C H 0.733099 0.453701 0.509200 0.081 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
O1 C10 1.3781(18) . ?
O1 C13 1.3648(19) . ?
O2 C14 1.2306(19) . ?
N1 C14 1.354(2) . ?
N1 C15 1.481(2) . ?
N1 C18 1.479(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.386(2) . ?
C1 C6 1.396(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.375(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(2) . ?
C6 C7 1.542(2) . ?
C7 C8 1.534(2) . ?
C7 C9 1.536(2) . ?
C7 C10 1.508(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.355(2) . ?
C11 C12 1.437(2) . ?
C11 C14 1.497(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.332(2) . ?
C13 H13 0.9500 . ?
C15 H15 1.0000 . ?
C15 C16 1.517(3) . ?
C15 C17 1.523(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18 1.0000 . ?
C18 C19 1.515(3) . ?
C18 C20 1.522(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
C13 O1 C10 107.11(12) . . ?
C14 N1 C15 122.93(14) . . ?
C14 N1 C18 119.49(14) . . ?
C18 N1 C15 117.56(13) . . ?
C2 C1 H1 119.7 . . ?
C2 C1 C6 120.58(15) . . ?
C6 C1 H1 119.7 . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.51(15) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.70(15) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.88(16) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.34(15) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C7 118.75(14) . . ?
C5 C6 C1 117.99(14) . . ?
C5 C6 C7 123.23(14) . . ?
C8 C7 C6 110.18(12) . . ?
C8 C7 C9 107.88(14) . . ?
C9 C7 C6 112.18(13) . . ?
C10 C7 C6 106.46(12) . . ?
C10 C7 C8 110.93(13) . . ?
C10 C7 C9 109.22(13) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 C7 113.74(13) . . ?
C11 C10 O1 109.18(13) . . ?
C11 C10 C7 137.02(14) . . ?
C10 C11 C12 106.42(14) . . ?
C10 C11 C14 128.37(14) . . ?
C12 C11 C14 124.81(14) . . ?
C11 C12 H12 126.6 . . ?
C13 C12 C11 106.86(14) . . ?
C13 C12 H12 126.6 . . ?
O1 C13 H13 124.8 . . ?
C12 C13 O1 110.42(14) . . ?
C12 C13 H13 124.8 . . ?
O2 C14 N1 122.41(15) . . ?
O2 C14 C11 119.74(14) . . ?
N1 C14 C11 117.82(14) . . ?
N1 C15 H15 107.3 . . ?
N1 C15 C16 111.71(15) . . ?
N1 C15 C17 111.38(16) . . ?
C16 C15 H15 107.3 . . ?
C16 C15 C17 111.47(16) . . ?
C17 C15 H15 107.3 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 H18 106.4 . . ?
N1 C18 C19 112.40(15) . . ?
N1 C18 C20 111.91(15) . . ?
C19 C18 H18 106.4 . . ?
C19 C18 C20 112.64(17) . . ?
C20 C18 H18 106.4 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
