# 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_20060
_database_code_depnum_ccdc_archive 'CCDC 2062906'
loop_
_audit_author_name
_audit_author_address
'Maren Pink'
;Indiana Univeristy
United States of America
;
_audit_update_record             
;
2021-02-13 deposited with the CCDC.	2021-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H29 N O3'
_chemical_formula_sum            'C15 H29 N O3'
_chemical_formula_weight         271.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_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                   12.3834(11)
_cell_length_b                   10.9459(9)
_cell_length_c                   12.0235(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.342(3)
_cell_angle_gamma                90
_cell_volume                     1629.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3060
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      25.73

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.106
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6470
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS, G. Sheldrick; 2018'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_details      
'0.50 degree frames measured for 3 seconds each'

_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            27891
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_av_R_equivalents  0.0936
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.483
_diffrn_reflns_theta_max         26.405
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3333
_reflns_number_gt                2405
_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       'BIS v6.2.9 (BrukerNano, 2018)'
_computing_cell_refinement       'SAINT V8.38A (BrukerNano, 2017)'
_computing_data_reduction        'SAINT V8.38A (BrukerNano, 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX3 v2018.1-0 (BrukerNano, 2018)'

_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)+(0.0537P)²+1.0551P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3333
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1394
_refine_ls_wR_factor_gt          0.1214
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_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
O1 O 0.22322(10) 0.22059(12) 0.22253(12) 0.0262(3) Uani 1 1 d . . . . .
O2 O 0.29070(10) 0.41445(12) 0.22463(11) 0.0241(3) Uani 1 1 d . . . . .
O3 O 0.57515(11) 0.11016(13) 0.25792(10) 0.0225(3) Uani 1 1 d . . . . .
H3O H 0.621(2) 0.050(3) 0.261(2) 0.054(8) Uiso 1 1 d . . . . .
N1 N 0.37934(12) 0.25628(13) 0.30630(13) 0.0189(3) Uani 1 1 d . . . . .
C1 C 0.39437(15) 0.12479(16) 0.32522(16) 0.0221(4) Uani 1 1 d . . . . .
H1A H 0.378673 0.077174 0.257016 0.026 Uiso 1 1 calc R U . . .
H1B H 0.347947 0.095042 0.386262 0.026 Uiso 1 1 calc R U . . .
C2 C 0.51390(15) 0.11736(16) 0.35691(15) 0.0189(4) Uani 1 1 d . . . . .
H2 H 0.528425 0.045702 0.406369 0.023 Uiso 1 1 calc R U . . .
C3 C 0.53560(14) 0.23917(16) 0.41859(14) 0.0173(4) Uani 1 1 d . . . . .
C4 C 0.47203(14) 0.32868(16) 0.34466(14) 0.0184(4) Uani 1 1 d . . . . .
H4A H 0.448132 0.400756 0.387736 0.022 Uiso 1 1 calc R U . . .
H4B H 0.516209 0.356571 0.281171 0.022 Uiso 1 1 calc R U . . .
C5 C 0.29750(14) 0.30575(17) 0.24905(15) 0.0198(4) Uani 1 1 d . . . . .
C6 C 0.12495(15) 0.2535(2) 0.15941(18) 0.0290(5) Uani 1 1 d . . . . .
C7 C 0.05981(16) 0.3475(2) 0.22258(19) 0.0335(5) Uani 1 1 d . . . . .
H7A H 0.048926 0.319233 0.299045 0.050 Uiso 1 1 calc R U . . .
H7B H -0.010437 0.358567 0.186005 0.050 Uiso 1 1 calc R U . . .
H7C H 0.098791 0.425372 0.223579 0.050 Uiso 1 1 calc R U . . .
C8 C 0.15536(18) 0.2962(2) 0.04367(18) 0.0387(6) Uani 1 1 d . . . . .
H8A H 0.196460 0.372461 0.049039 0.058 Uiso 1 1 calc R U . . .
H8B H 0.089654 0.309964 -0.000387 0.058 Uiso 1 1 calc R U . . .
H8C H 0.199614 0.233571 0.007614 0.058 Uiso 1 1 calc R U . . .
C9 C 0.06539(18) 0.1322(2) 0.1554(2) 0.0439(6) Uani 1 1 d . . . . .
H9A H 0.047309 0.106600 0.231127 0.066 Uiso 1 1 calc R U . . .
H9B H 0.111545 0.070292 0.120859 0.066 Uiso 1 1 calc R U . . .
H9C H -0.001091 0.141345 0.111539 0.066 Uiso 1 1 calc R U . . .
C10 C 0.65686(15) 0.27227(17) 0.42226(15) 0.0215(4) Uani 1 1 d . . . . .
H10 H 0.679931 0.277057 0.342820 0.026 Uiso 1 1 calc R U . . .
C11 C 0.73044(16) 0.17435(19) 0.47655(16) 0.0261(4) Uani 1 1 d . . . . .
H11 H 0.696242 0.092897 0.462966 0.031 Uiso 1 1 calc R U . . .
C12 C 0.84075(17) 0.1739(2) 0.41910(19) 0.0372(5) Uani 1 1 d . . . . .
H12A H 0.887251 0.112032 0.453744 0.056 Uiso 1 1 calc R U . . .
H12B H 0.874393 0.254492 0.426825 0.056 Uiso 1 1 calc R U . . .
H12C H 0.831072 0.154794 0.340029 0.056 Uiso 1 1 calc R U . . .
C13 C 0.74657(18) 0.1880(2) 0.60224(17) 0.0345(5) Uani 1 1 d . . . . .
H13A H 0.785437 0.116593 0.631123 0.052 Uiso 1 1 calc R U . . .
H13B H 0.676059 0.193973 0.638406 0.052 Uiso 1 1 calc R U . . .
H13C H 0.788542 0.262003 0.617663 0.052 Uiso 1 1 calc R U . . .
C14 C 0.67653(17) 0.40075(19) 0.47077(18) 0.0297(5) Uani 1 1 d . . . . .
H14A H 0.754034 0.418794 0.470103 0.045 Uiso 1 1 calc R U . . .
H14B H 0.650113 0.403745 0.547391 0.045 Uiso 1 1 calc R U . . .
H14C H 0.637935 0.461412 0.425652 0.045 Uiso 1 1 calc R U . . .
C15 C 0.48245(15) 0.23342(18) 0.53372(15) 0.0230(4) Uani 1 1 d . . . . .
H15A H 0.499859 0.307805 0.575491 0.035 Uiso 1 1 calc R U . . .
H15B H 0.509652 0.162028 0.574314 0.035 Uiso 1 1 calc R U . . .
H15C H 0.403963 0.226758 0.524730 0.035 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 C5 1.347(2) . ?
O1 C6 1.475(2) . ?
O2 C5 1.228(2) . ?
O3 C2 1.417(2) . ?
O3 H3O 0.87(3) . ?
N1 C5 1.336(2) . ?
N1 C4 1.467(2) . ?
N1 C1 1.469(2) . ?
C1 C2 1.528(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.548(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.537(2) . ?
C3 C15 1.538(2) . ?
C3 C10 1.545(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C6 C7 1.514(3) . ?
C6 C8 1.517(3) . ?
C6 C9 1.520(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
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 C14 1.541(3) . ?
C10 C11 1.549(3) . ?
C10 H10 1.0000 . ?
C11 C13 1.530(3) . ?
C11 C12 1.535(3) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C5 O1 C6 120.85(15) . . ?
C2 O3 H3O 111.0(18) . . ?
C5 N1 C4 122.18(15) . . ?
C5 N1 C1 124.88(15) . . ?
C4 N1 C1 112.49(14) . . ?
N1 C1 C2 102.26(14) . . ?
N1 C1 H1A 111.3 . . ?
C2 C1 H1A 111.3 . . ?
N1 C1 H1B 111.3 . . ?
C2 C1 H1B 111.3 . . ?
H1A C1 H1B 109.2 . . ?
O3 C2 C1 108.42(15) . . ?
O3 C2 C3 110.97(14) . . ?
C1 C2 C3 103.80(14) . . ?
O3 C2 H2 111.1 . . ?
C1 C2 H2 111.1 . . ?
C3 C2 H2 111.1 . . ?
C4 C3 C15 109.05(15) . . ?
C4 C3 C10 111.19(14) . . ?
C15 C3 C10 113.89(14) . . ?
C4 C3 C2 100.67(13) . . ?
C15 C3 C2 108.78(14) . . ?
C10 C3 C2 112.42(14) . . ?
N1 C4 C3 103.57(14) . . ?
N1 C4 H4A 111.0 . . ?
C3 C4 H4A 111.0 . . ?
N1 C4 H4B 111.0 . . ?
C3 C4 H4B 111.0 . . ?
H4A C4 H4B 109.0 . . ?
O2 C5 N1 124.50(17) . . ?
O2 C5 O1 124.63(17) . . ?
N1 C5 O1 110.87(16) . . ?
O1 C6 C7 110.38(17) . . ?
O1 C6 C8 109.78(16) . . ?
C7 C6 C8 112.78(19) . . ?
O1 C6 C9 101.62(16) . . ?
C7 C6 C9 110.47(18) . . ?
C8 C6 C9 111.3(2) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C14 C10 C3 112.09(15) . . ?
C14 C10 C11 112.38(16) . . ?
C3 C10 C11 114.78(15) . . ?
C14 C10 H10 105.6 . . ?
C3 C10 H10 105.6 . . ?
C11 C10 H10 105.6 . . ?
C13 C11 C12 109.48(17) . . ?
C13 C11 C10 114.95(17) . . ?
C12 C11 C10 109.62(17) . . ?
C13 C11 H11 107.5 . . ?
C12 C11 H11 107.5 . . ?
C10 C11 H11 107.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C3 C15 H15A 109.5 . . ?
C3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C5 N1 C1 C2 161.19(17) . . . . ?
C4 N1 C1 C2 -11.21(19) . . . . ?
N1 C1 C2 O3 -85.38(16) . . . . ?
N1 C1 C2 C3 32.68(17) . . . . ?
O3 C2 C3 C4 74.73(17) . . . . ?
C1 C2 C3 C4 -41.55(17) . . . . ?
O3 C2 C3 C15 -170.76(14) . . . . ?
C1 C2 C3 C15 72.96(17) . . . . ?
O3 C2 C3 C10 -43.67(19) . . . . ?
C1 C2 C3 C10 -159.94(14) . . . . ?
C5 N1 C4 C3 172.48(16) . . . . ?
C1 N1 C4 C3 -14.88(19) . . . . ?
C15 C3 C4 N1 -80.35(17) . . . . ?
C10 C3 C4 N1 153.25(14) . . . . ?
C2 C3 C4 N1 33.96(16) . . . . ?
C4 N1 C5 O2 -1.1(3) . . . . ?
C1 N1 C5 O2 -172.82(18) . . . . ?
C4 N1 C5 O1 179.35(15) . . . . ?
C1 N1 C5 O1 7.6(2) . . . . ?
C6 O1 C5 O2 0.3(3) . . . . ?
C6 O1 C5 N1 179.79(16) . . . . ?
C5 O1 C6 C7 -60.0(2) . . . . ?
C5 O1 C6 C8 64.9(2) . . . . ?
C5 O1 C6 C9 -177.21(18) . . . . ?
C4 C3 C10 C14 60.95(19) . . . . ?
C15 C3 C10 C14 -62.7(2) . . . . ?
C2 C3 C10 C14 172.95(15) . . . . ?
C4 C3 C10 C11 -169.26(15) . . . . ?
C15 C3 C10 C11 67.1(2) . . . . ?
C2 C3 C10 C11 -57.3(2) . . . . ?
C14 C10 C11 C13 40.0(2) . . . . ?
C3 C10 C11 C13 -89.7(2) . . . . ?
C14 C10 C11 C12 -83.8(2) . . . . ?
C3 C10 C11 C12 146.52(17) . . . . ?

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
O3 H3O O2 0.87(3) 1.85(3) 2.7182(19) 175(3) 2_645 yes
C7 H7C O2 0.98 2.38 2.952(2) 116.6 . yes
C8 H8A O2 0.98 2.45 3.029(3) 117.5 . yes

_refine_diff_density_max         0.489
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.050



