# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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. 
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data_20170329b_0m
_database_code_depnum_ccdc_archive 'CCDC 1547404'
_audit_update_record             
;
2017-05-02 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H29 N3 O3'
_chemical_formula_weight         371.47

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   16.772(3)
_cell_length_b                   9.0637(15)
_cell_length_c                   25.832(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3926.9(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_F_000             1600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12896
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.577
_diffrn_reflns_theta_max         18.305
_diffrn_reflns_theta_full        18.305
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1411
_reflns_number_gt                1166
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0644P)²+1.4613P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1411
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.1026
_refine_ls_wR_factor_gt          0.0965
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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
O2 O 0.31919(14) 0.0746(2) -0.12907(9) 0.0603(7) Uani 1 1 d . . . . .
H2 H 0.2913 0.1461 -0.1221 0.090 Uiso 1 1 calc R U . . .
O1 O 0.41331(15) 0.7413(2) 0.10785(9) 0.0617(8) Uani 1 1 d . . . . .
H1 H 0.4069 0.6590 0.0954 0.093 Uiso 1 1 calc R U . . .
O3 O 0.27134(13) -0.1943(3) -0.09449(9) 0.0677(8) Uani 1 1 d . . . . .
H3 H 0.2848 -0.1155 -0.1075 0.101 Uiso 1 1 d R U . . .
N3 N 0.39423(15) -0.0170(3) -0.03113(11) 0.0416(8) Uani 1 1 d . . . . .
N2 N 0.36741(16) 0.4746(3) 0.10145(13) 0.0477(8) Uani 1 1 d . . . . .
N1 N 0.39142(17) 0.9916(3) 0.26832(11) 0.0517(8) Uani 1 1 d . . . . .
C15 C 0.38786(19) 0.0998(5) 0.00320(13) 0.0383(9) Uani 1 1 d . . . . .
C8 C 0.3414(2) 0.6211(4) 0.17585(15) 0.0401(9) Uani 1 1 d . . . . .
C12 C 0.3707(2) 0.3447(5) 0.07102(15) 0.0429(9) Uani 1 1 d . . . . .
C9 C 0.3842(2) 0.7440(5) 0.15609(14) 0.0419(10) Uani 1 1 d . . . . .
C5 C 0.3723(2) 0.8747(4) 0.23739(16) 0.0413(9) Uani 1 1 d . . . . .
C10 C 0.39673(19) 0.8674(4) 0.18599(16) 0.0441(10) Uani 1 1 d . . . . .
H10 H 0.4223 0.9483 0.1714 0.053 Uiso 1 1 calc R U . . .
C13 C 0.3289(2) 0.2140(5) 0.07949(13) 0.0461(10) Uani 1 1 d . . . . .
H13 H 0.2949 0.2067 0.1078 0.055 Uiso 1 1 calc R U . . .
C7 C 0.3134(2) 0.6339(4) 0.22636(17) 0.0533(10) Uani 1 1 d . . . . .
H7 H 0.2833 0.5569 0.2400 0.064 Uiso 1 1 calc R U . . .
C16 C 0.43148(19) 0.2303(5) -0.00365(13) 0.0438(9) Uani 1 1 d . . . . .
H16 H 0.4673 0.2375 -0.0310 0.053 Uiso 1 1 calc R U . . .
C20 C 0.43694(19) 0.0007(4) -0.07988(12) 0.0466(10) Uani 1 1 d . . . . .
H20A H 0.4407 -0.0951 -0.0965 0.056 Uiso 1 1 calc R U . . .
H20B H 0.4908 0.0331 -0.0723 0.056 Uiso 1 1 calc R U . . .
C6 C 0.3278(2) 0.7534(5) 0.25675(14) 0.0510(10) Uani 1 1 d . . . . .
H6 H 0.3084 0.7557 0.2905 0.061 Uiso 1 1 calc R U . . .
C17 C 0.4221(2) 0.3473(4) 0.02927(16) 0.0493(10) Uani 1 1 d . . . . .
H17 H 0.4517 0.4323 0.0233 0.059 Uiso 1 1 calc R U . . .
C14 C 0.3372(2) 0.0954(4) 0.04659(15) 0.0461(10) Uani 1 1 d . . . . .
H14 H 0.3084 0.0098 0.0533 0.055 Uiso 1 1 calc R U . . .
C11 C 0.3338(2) 0.4881(4) 0.14574(17) 0.0478(10) Uani 1 1 d . . . . .
H11 H 0.3037 0.4103 0.1587 0.057 Uiso 1 1 calc R U . . .
C18 C 0.3596(2) -0.1606(4) -0.02001(13) 0.0505(10) Uani 1 1 d . . . . .
H18A H 0.3593 -0.1747 0.0172 0.061 Uiso 1 1 calc R U . . .
H18B H 0.3939 -0.2359 -0.0347 0.061 Uiso 1 1 calc R U . . .
C21 C 0.4004(2) 0.1078(4) -0.11777(13) 0.0524(10) Uani 1 1 d . . . . .
H21A H 0.4036 0.2067 -0.1036 0.063 Uiso 1 1 calc R U . . .
H21B H 0.4309 0.1061 -0.1497 0.063 Uiso 1 1 calc R U . . .
C4 C 0.3590(2) 1.0144(4) 0.31972(14) 0.0586(11) Uani 1 1 d . . . . .
H4A H 0.3075 0.9661 0.3218 0.070 Uiso 1 1 calc R U . . .
H4B H 0.3505 1.1192 0.3249 0.070 Uiso 1 1 calc R U . . .
C2 C 0.4521(2) 1.1022(4) 0.25212(14) 0.0652(11) Uani 1 1 d . . . . .
H2A H 0.4800 1.1380 0.2825 0.078 Uiso 1 1 calc R U . . .
H2B H 0.4909 1.0547 0.2298 0.078 Uiso 1 1 calc R U . . .
C19 C 0.2766(2) -0.1840(4) -0.03991(14) 0.0652(12) Uani 1 1 d . . . . .
H19A H 0.2555 -0.2740 -0.0249 0.078 Uiso 1 1 calc R U . . .
H19B H 0.2434 -0.1030 -0.0283 0.078 Uiso 1 1 calc R U . . .
C1 C 0.4165(3) 1.2289(4) 0.22430(15) 0.0886(14) Uani 1 1 d . . . . .
H1A H 0.3895 1.1943 0.1939 0.133 Uiso 1 1 calc R U . . .
H1B H 0.4578 1.2967 0.2145 0.133 Uiso 1 1 calc R U . . .
H1C H 0.3790 1.2780 0.2465 0.133 Uiso 1 1 calc R U . . .
C3 C 0.4113(3) 0.9571(5) 0.36259(15) 0.0837(13) Uani 1 1 d . . . . .
H3A H 0.4186 0.8527 0.3585 0.125 Uiso 1 1 calc R U . . .
H3B H 0.3866 0.9766 0.3954 0.125 Uiso 1 1 calc R U . . .
H3C H 0.4622 1.0054 0.3612 0.125 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
O2 C21 1.425(4) . ?
O2 H2 0.8200 . ?
O1 C9 1.339(4) . ?
O1 H1 0.8200 . ?
O3 C19 1.416(4) . ?
O3 H3 0.8199 . ?
N3 C15 1.385(4) . ?
N3 C18 1.454(4) . ?
N3 C20 1.458(4) . ?
N2 C11 1.282(4) . ?
N2 C12 1.417(4) . ?
N1 C5 1.366(4) . ?
N1 C4 1.449(4) . ?
N1 C2 1.488(4) . ?
C15 C16 1.402(4) . ?
C15 C14 1.407(4) . ?
C8 C7 1.392(4) . ?
C8 C9 1.420(4) . ?
C8 C11 1.440(5) . ?
C12 C17 1.381(4) . ?
C12 C13 1.393(4) . ?
C9 C10 1.375(4) . ?
C5 C10 1.391(4) . ?
C5 C6 1.419(4) . ?
C10 H10 0.9300 . ?
C13 C14 1.377(4) . ?
C13 H13 0.9300 . ?
C7 C6 1.360(4) . ?
C7 H7 0.9300 . ?
C16 C17 1.368(4) . ?
C16 H16 0.9300 . ?
C20 C21 1.509(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C6 H6 0.9300 . ?
C17 H17 0.9300 . ?
C14 H14 0.9300 . ?
C11 H11 0.9300 . ?
C18 C19 1.499(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C4 C3 1.505(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C2 C1 1.481(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?

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
C21 O2 H2 109.5 . . ?
C9 O1 H1 109.5 . . ?
C19 O3 H3 109.4 . . ?
C15 N3 C18 121.8(3) . . ?
C15 N3 C20 120.5(3) . . ?
C18 N3 C20 117.7(3) . . ?
C11 N2 C12 126.3(3) . . ?
C5 N1 C4 123.9(3) . . ?
C5 N1 C2 121.2(3) . . ?
C4 N1 C2 114.7(3) . . ?
N3 C15 C16 121.6(3) . . ?
N3 C15 C14 122.4(4) . . ?
C16 C15 C14 116.1(3) . . ?
C7 C8 C9 116.3(3) . . ?
C7 C8 C11 123.1(4) . . ?
C9 C8 C11 120.5(3) . . ?
C17 C12 C13 116.8(3) . . ?
C17 C12 N2 116.3(4) . . ?
C13 C12 N2 126.9(4) . . ?
O1 C9 C10 118.8(4) . . ?
O1 C9 C8 120.3(4) . . ?
C10 C9 C8 120.9(3) . . ?
N1 C5 C10 121.7(4) . . ?
N1 C5 C6 121.2(4) . . ?
C10 C5 C6 117.0(3) . . ?
C9 C10 C5 122.0(3) . . ?
C9 C10 H10 119.0 . . ?
C5 C10 H10 119.0 . . ?
C14 C13 C12 121.0(3) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C6 C7 C8 123.2(3) . . ?
C6 C7 H7 118.4 . . ?
C8 C7 H7 118.4 . . ?
C17 C16 C15 121.0(3) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
N3 C20 C21 115.5(3) . . ?
N3 C20 H20A 108.4 . . ?
C21 C20 H20A 108.4 . . ?
N3 C20 H20B 108.4 . . ?
C21 C20 H20B 108.4 . . ?
H20A C20 H20B 107.5 . . ?
C7 C6 C5 120.5(3) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C16 C17 C12 122.9(3) . . ?
C16 C17 H17 118.5 . . ?
C12 C17 H17 118.5 . . ?
C13 C14 C15 122.0(3) . . ?
C13 C14 H14 119.0 . . ?
C15 C14 H14 119.0 . . ?
N2 C11 C8 121.5(3) . . ?
N2 C11 H11 119.2 . . ?
C8 C11 H11 119.2 . . ?
N3 C18 C19 115.5(3) . . ?
N3 C18 H18A 108.4 . . ?
C19 C18 H18A 108.4 . . ?
N3 C18 H18B 108.4 . . ?
C19 C18 H18B 108.4 . . ?
H18A C18 H18B 107.5 . . ?
O2 C21 C20 112.7(3) . . ?
O2 C21 H21A 109.1 . . ?
C20 C21 H21A 109.1 . . ?
O2 C21 H21B 109.1 . . ?
C20 C21 H21B 109.1 . . ?
H21A C21 H21B 107.8 . . ?
N1 C4 C3 114.0(3) . . ?
N1 C4 H4A 108.8 . . ?
C3 C4 H4A 108.8 . . ?
N1 C4 H4B 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C1 C2 N1 112.5(3) . . ?
C1 C2 H2A 109.1 . . ?
N1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
N1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
O3 C19 C18 114.2(3) . . ?
O3 C19 H19A 108.7 . . ?
C18 C19 H19A 108.7 . . ?
O3 C19 H19B 108.7 . . ?
C18 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 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
C18 N3 C15 C16 169.8(3) . . . . ?
C20 N3 C15 C16 -9.7(4) . . . . ?
C18 N3 C15 C14 -10.6(4) . . . . ?
C20 N3 C15 C14 169.9(3) . . . . ?
C11 N2 C12 C17 -168.5(3) . . . . ?
C11 N2 C12 C13 9.9(5) . . . . ?
C7 C8 C9 O1 -180.0(3) . . . . ?
C11 C8 C9 O1 4.5(5) . . . . ?
C7 C8 C9 C10 0.3(4) . . . . ?
C11 C8 C9 C10 -175.3(3) . . . . ?
C4 N1 C5 C10 171.5(3) . . . . ?
C2 N1 C5 C10 -12.1(5) . . . . ?
C4 N1 C5 C6 -9.8(5) . . . . ?
C2 N1 C5 C6 166.5(3) . . . . ?
O1 C9 C10 C5 -176.2(3) . . . . ?
C8 C9 C10 C5 3.6(5) . . . . ?
N1 C5 C10 C9 173.7(3) . . . . ?
C6 C5 C10 C9 -5.0(5) . . . . ?
C17 C12 C13 C14 -1.9(5) . . . . ?
N2 C12 C13 C14 179.6(3) . . . . ?
C9 C8 C7 C6 -2.6(5) . . . . ?
C11 C8 C7 C6 172.9(3) . . . . ?
N3 C15 C16 C17 177.2(3) . . . . ?
C14 C15 C16 C17 -2.4(4) . . . . ?
C15 N3 C20 C21 -65.2(4) . . . . ?
C18 N3 C20 C21 115.3(3) . . . . ?
C8 C7 C6 C5 1.1(5) . . . . ?
N1 C5 C6 C7 -176.0(3) . . . . ?
C10 C5 C6 C7 2.7(5) . . . . ?
C15 C16 C17 C12 0.6(5) . . . . ?
C13 C12 C17 C16 1.6(5) . . . . ?
N2 C12 C17 C16 -179.8(3) . . . . ?
C12 C13 C14 C15 0.1(5) . . . . ?
N3 C15 C14 C13 -177.5(3) . . . . ?
C16 C15 C14 C13 2.0(4) . . . . ?
C12 N2 C11 C8 173.2(3) . . . . ?
C7 C8 C11 N2 -172.6(3) . . . . ?
C9 C8 C11 N2 2.6(5) . . . . ?
C15 N3 C18 C19 92.2(4) . . . . ?
C20 N3 C18 C19 -88.2(4) . . . . ?
N3 C20 C21 O2 -54.6(4) . . . . ?
C5 N1 C4 C3 95.5(4) . . . . ?
C2 N1 C4 C3 -81.0(4) . . . . ?
C5 N1 C2 C1 91.8(4) . . . . ?
C4 N1 C2 C1 -91.5(4) . . . . ?
N3 C18 C19 O3 69.5(4) . . . . ?

_refine_diff_density_max         0.189
_refine_diff_density_min         -0.110
_refine_diff_density_rms         0.029

