# 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_K368
_database_code_depnum_ccdc_archive 'CCDC 2034197'
loop_
_audit_author_name
_audit_author_address
'YA CHEN'
;National University of Singapore
Singapore
;
_audit_update_record             
;
2020-09-28 deposited with the CCDC.	2021-07-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H27 N'
_chemical_formula_weight         293.43

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   5.9597(2)
_cell_length_b                   18.2988(6)
_cell_length_c                   16.5207(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.303(2)
_cell_angle_gamma                90
_cell_volume                     1790.78(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9913
_cell_measurement_theta_min      3.62
_cell_measurement_theta_max      70.07

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.088
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.056
_exptl_absorpt_coefficient_mu    0.464
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6937
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14003
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.616
_diffrn_reflns_theta_max         70.159
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3392
_reflns_number_gt                3130
_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_bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'APEX3 v2016.1-0 (Bruker AXS)'
_computing_data_collection       'APEX3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL--2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXT--(Sheldrick 2015)'
_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)+(0.0496P)²+0.6958P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     Dual-space
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3392
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1112
_refine_ls_wR_factor_gt          0.1088
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
N1 N 0.7291(2) 0.23022(7) 0.37584(8) 0.0383(3) Uani 1 1 d . . . . .
C1 C 0.1573(2) 0.21147(6) 0.58489(7) 0.0228(3) Uani 1 1 d . . . . .
H1 H 0.078767 0.244346 0.542472 0.027 Uiso 1 1 calc R U . . .
C2 C -0.0204(2) 0.16909(7) 0.62703(8) 0.0284(3) Uani 1 1 d . . . . .
H2A H 0.043203 0.153264 0.682118 0.034 Uiso 1 1 calc R U . . .
H2B H -0.154171 0.200140 0.632153 0.034 Uiso 1 1 calc R U . . .
C3 C -0.0858(2) 0.10250(8) 0.57292(9) 0.0359(3) Uani 1 1 d . . . . .
H3A H -0.079941 0.057296 0.606007 0.043 Uiso 1 1 calc R U . . .
H3B H -0.240458 0.108251 0.545028 0.043 Uiso 1 1 calc R U . . .
C4 C 0.0863(2) 0.09898(7) 0.51069(9) 0.0324(3) Uani 1 1 d . . . . .
H4A H 0.143250 0.048496 0.506033 0.039 Uiso 1 1 calc R U . . .
H4B H 0.017098 0.115179 0.456441 0.039 Uiso 1 1 calc R U . . .
C5 C 0.2773(2) 0.15026(7) 0.54287(8) 0.0278(3) Uani 1 1 d . . . . .
H5A H 0.356017 0.169886 0.497792 0.033 Uiso 1 1 calc R U . . .
H5B H 0.388303 0.124812 0.582089 0.033 Uiso 1 1 calc R U . . .
C6 C 0.3102(2) 0.25710(6) 0.64491(7) 0.0224(3) Uani 1 1 d . . . . .
H6A H 0.214023 0.287769 0.676427 0.027 Uiso 1 1 calc R U . . .
H6B H 0.396415 0.223589 0.683792 0.027 Uiso 1 1 calc R U . . .
C7 C 0.4768(2) 0.30663(6) 0.60804(7) 0.0210(3) Uani 1 1 d . . . . .
C8 C 0.6437(2) 0.34873(6) 0.66366(7) 0.0210(3) Uani 1 1 d . . . . .
C9 C 0.8306(2) 0.38143(7) 0.63481(7) 0.0247(3) Uani 1 1 d . . . . .
H9 H 0.851127 0.377038 0.578800 0.030 Uiso 1 1 calc R U . . .
C10 C 0.9871(2) 0.42020(7) 0.68612(8) 0.0271(3) Uani 1 1 d . . . . .
H10 H 1.113371 0.441616 0.664802 0.033 Uiso 1 1 calc R U . . .
C11 C 0.9622(2) 0.42830(7) 0.76839(8) 0.0279(3) Uani 1 1 d . . . . .
C12 C 0.7756(2) 0.39592(8) 0.79705(8) 0.0323(3) Uani 1 1 d . . . . .
H12 H 0.754950 0.400869 0.852986 0.039 Uiso 1 1 calc R U . . .
C13 C 0.6184(2) 0.35653(7) 0.74638(8) 0.0278(3) Uani 1 1 d . . . . .
H13 H 0.493066 0.334770 0.767984 0.033 Uiso 1 1 calc R U . . .
C14 C 1.1335(3) 0.46962(8) 0.82461(9) 0.0390(3) Uani 1 1 d . . . . .
H14A H 1.200082 0.508500 0.794175 0.058 Uiso 1 1 calc R U . . .
H14B H 1.252436 0.436075 0.847198 0.058 Uiso 1 1 calc R U . . .
H14C H 1.059391 0.491162 0.869038 0.058 Uiso 1 1 calc R U . . .
C15 C 0.4778(2) 0.31213(6) 0.52883(7) 0.0244(3) Uani 1 1 d . . . . .
C16 C 0.4806(2) 0.31943(6) 0.44973(7) 0.0233(3) Uani 1 1 d . . . . .
C17 C 0.6198(2) 0.26979(7) 0.40891(8) 0.0270(3) Uani 1 1 d . . . . .
C18 C 0.3497(2) 0.37762(7) 0.39670(7) 0.0260(3) Uani 1 1 d . . . . .
C19 C 0.2040(2) 0.33998(8) 0.32662(8) 0.0338(3) Uani 1 1 d . . . . .
H19A H 0.126526 0.377047 0.290974 0.051 Uiso 1 1 calc R U . . .
H19B H 0.092029 0.308684 0.348742 0.051 Uiso 1 1 calc R U . . .
H19C H 0.300302 0.310125 0.295314 0.051 Uiso 1 1 calc R U . . .
C20 C 0.5202(2) 0.42889(7) 0.36234(8) 0.0322(3) Uani 1 1 d . . . . .
H20A H 0.617368 0.400535 0.329866 0.048 Uiso 1 1 calc R U . . .
H20B H 0.613131 0.452779 0.407368 0.048 Uiso 1 1 calc R U . . .
H20C H 0.438983 0.466054 0.327889 0.048 Uiso 1 1 calc R U . . .
C21 C 0.1993(3) 0.42060(8) 0.44947(9) 0.0353(3) Uani 1 1 d . . . . .
H21A H 0.118900 0.458983 0.416619 0.053 Uiso 1 1 calc R U . . .
H21B H 0.293170 0.442866 0.495356 0.053 Uiso 1 1 calc R U . . .
H21C H 0.089808 0.387414 0.470154 0.053 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
N1 C17 1.1511(17) . ?
C1 C6 1.5207(17) . ?
C1 C5 1.5353(16) . ?
C1 C2 1.5395(16) . ?
C1 H1 1.0000 . ?
C2 C3 1.5360(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5310(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5252(18) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.5202(16) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C15 1.3132(17) . ?
C7 C8 1.4921(16) . ?
C8 C9 1.3939(17) . ?
C8 C13 1.3986(17) . ?
C9 C10 1.3848(18) . ?
C9 H9 0.9500 . ?
C10 C11 1.3911(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(2) . ?
C11 C14 1.5059(18) . ?
C12 C13 1.3876(19) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.3154(17) . ?
C16 C17 1.4461(17) . ?
C16 C18 1.5362(17) . ?
C18 C19 1.5323(18) . ?
C18 C21 1.5340(18) . ?
C18 C20 1.5371(17) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C6 C1 C5 114.83(10) . . ?
C6 C1 C2 111.99(10) . . ?
C5 C1 C2 102.41(9) . . ?
C6 C1 H1 109.1 . . ?
C5 C1 H1 109.1 . . ?
C2 C1 H1 109.1 . . ?
C3 C2 C1 106.22(10) . . ?
C3 C2 H2A 110.5 . . ?
C1 C2 H2A 110.5 . . ?
C3 C2 H2B 110.5 . . ?
C1 C2 H2B 110.5 . . ?
H2A C2 H2B 108.7 . . ?
C4 C3 C2 106.17(11) . . ?
C4 C3 H3A 110.5 . . ?
C2 C3 H3A 110.5 . . ?
C4 C3 H3B 110.5 . . ?
C2 C3 H3B 110.5 . . ?
H3A C3 H3B 108.7 . . ?
C5 C4 C3 105.63(11) . . ?
C5 C4 H4A 110.6 . . ?
C3 C4 H4A 110.6 . . ?
C5 C4 H4B 110.6 . . ?
C3 C4 H4B 110.6 . . ?
H4A C4 H4B 108.7 . . ?
C4 C5 C1 103.86(10) . . ?
C4 C5 H5A 111.0 . . ?
C1 C5 H5A 111.0 . . ?
C4 C5 H5B 111.0 . . ?
C1 C5 H5B 111.0 . . ?
H5A C5 H5B 109.0 . . ?
C7 C6 C1 115.91(10) . . ?
C7 C6 H6A 108.3 . . ?
C1 C6 H6A 108.3 . . ?
C7 C6 H6B 108.3 . . ?
C1 C6 H6B 108.3 . . ?
H6A C6 H6B 107.4 . . ?
C15 C7 C8 119.89(11) . . ?
C15 C7 C6 121.32(11) . . ?
C8 C7 C6 118.79(10) . . ?
C9 C8 C13 117.79(11) . . ?
C9 C8 C7 120.99(10) . . ?
C13 C8 C7 121.22(11) . . ?
C10 C9 C8 121.35(11) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C11 121.07(12) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 117.56(12) . . ?
C12 C11 C14 121.20(12) . . ?
C10 C11 C14 121.23(12) . . ?
C13 C12 C11 121.94(12) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C12 C13 C8 120.29(12) . . ?
C12 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 C15 C16 178.49(13) . . ?
C15 C16 C17 118.02(11) . . ?
C15 C16 C18 125.17(11) . . ?
C17 C16 C18 116.81(10) . . ?
N1 C17 C16 179.37(15) . . ?
C19 C18 C21 110.01(11) . . ?
C19 C18 C16 109.24(10) . . ?
C21 C18 C16 108.85(10) . . ?
C19 C18 C20 109.76(10) . . ?
C21 C18 C20 110.38(11) . . ?
C16 C18 C20 108.57(10) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
C6 C1 C2 C3 -154.86(11) . . . . ?
C5 C1 C2 C3 -31.32(13) . . . . ?
C1 C2 C3 C4 11.04(15) . . . . ?
C2 C3 C4 C5 13.90(15) . . . . ?
C3 C4 C5 C1 -33.63(14) . . . . ?
C6 C1 C5 C4 161.46(10) . . . . ?
C2 C1 C5 C4 39.84(12) . . . . ?
C5 C1 C6 C7 69.43(13) . . . . ?
C2 C1 C6 C7 -174.33(10) . . . . ?
C1 C6 C7 C15 3.66(16) . . . . ?
C1 C6 C7 C8 -175.45(10) . . . . ?
C15 C7 C8 C9 -13.85(17) . . . . ?
C6 C7 C8 C9 165.28(10) . . . . ?
C15 C7 C8 C13 166.35(12) . . . . ?
C6 C7 C8 C13 -14.53(16) . . . . ?
C13 C8 C9 C10 0.23(17) . . . . ?
C7 C8 C9 C10 -179.59(11) . . . . ?
C8 C9 C10 C11 -0.43(19) . . . . ?
C9 C10 C11 C12 0.21(18) . . . . ?
C9 C10 C11 C14 179.23(12) . . . . ?
C10 C11 C12 C13 0.21(19) . . . . ?
C14 C11 C12 C13 -178.81(12) . . . . ?
C11 C12 C13 C8 -0.4(2) . . . . ?
C9 C8 C13 C12 0.19(18) . . . . ?
C7 C8 C13 C12 180.00(11) . . . . ?
C15 C16 C18 C19 -125.42(13) . . . . ?
C17 C16 C18 C19 55.53(14) . . . . ?
C15 C16 C18 C21 -5.29(17) . . . . ?
C17 C16 C18 C21 175.67(11) . . . . ?
C15 C16 C18 C20 114.90(13) . . . . ?
C17 C16 C18 C20 -64.14(14) . . . . ?

_refine_diff_density_max         0.273
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.038



