# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_sm_ag1w_a
_database_code_depnum_ccdc_archive 'CCDC 1829442'
loop_
_audit_author_name
_audit_author_address
'Jerome Marrot'
;Institut Lavoisier de Versailles
France
;
_audit_update_record             
;
2018-03-13 deposited with the CCDC.	2019-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H27 N3 O3'
_chemical_formula_weight         381.46

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   13.957(2)
_cell_length_b                   5.4550(9)
_cell_length_c                   14.7103(19)
_cell_angle_alpha                90
_cell_angle_beta                 107.844(9)
_cell_angle_gamma                90
_cell_volume                     1066.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5098
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      24.95

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   0.5174
_exptl_transmission_factor_max   0.7452
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Sheldrick, V2016/2)'
_exptl_absorpt_special_details   
'Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10'
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microsource
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17176
_diffrn_reflns_av_unetI/netI     0.1043
_diffrn_reflns_av_R_equivalents  0.1424
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.415
_diffrn_reflns_theta_max         25.163
_diffrn_reflns_theta_full        25.163
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_point_group_measured_fraction_full 0.928
_reflns_number_total             3545
_reflns_number_gt                2449
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_max     0.876
_reflns_Friedel_fraction_full    0.876

_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0405P)²+0.7546P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 804 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3545
_refine_ls_number_parameters     261
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1065
_refine_ls_R_factor_gt           0.0666
_refine_ls_wR_factor_ref         0.1579
_refine_ls_wR_factor_gt          0.1414
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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
C1 C 0.0503(6) 1.049(2) 0.8824(7) 0.099(4) Uani 1 1 d . . . . .
H1A H 0.037074 0.948545 0.932518 0.149 Uiso 1 1 calc R U . . .
H1B H 0.037330 0.951643 0.823809 0.149 Uiso 1 1 calc R U . . .
H1C H 0.006137 1.192621 0.870022 0.149 Uiso 1 1 calc R U . . .
C2 C 0.1867(6) 1.2534(17) 1.0095(6) 0.075(3) Uani 1 1 d . . . . .
H2A H 0.181910 1.134569 1.057864 0.113 Uiso 1 1 calc R U . . .
H2B H 0.140159 1.389456 1.007263 0.113 Uiso 1 1 calc R U . . .
H2C H 0.255617 1.316321 1.025804 0.113 Uiso 1 1 calc R U . . .
C3 C 0.1598(5) 1.1320(14) 0.9148(5) 0.0532(19) Uani 1 1 d . . . . .
H3 H 0.169186 1.253240 0.867217 0.064 Uiso 1 1 calc R U . . .
C4 C 0.2287(4) 0.9118(12) 0.9162(4) 0.0342(15) Uani 1 1 d . . . . .
H4A H 0.225271 0.798515 0.967690 0.041 Uiso 1 1 calc R U . . .
H4B H 0.203142 0.822834 0.854823 0.041 Uiso 1 1 calc R U . . .
C5 C 0.3386(4) 0.9814(10) 0.9317(4) 0.0275(14) Uani 1 1 d . . . . .
H5 H 0.365748 1.065162 0.994878 0.033 Uiso 1 1 calc R U . . .
N6 N 0.3521(4) 1.1426(9) 0.8562(3) 0.0274(12) Uani 1 1 d . . . . .
H6A H 0.395(5) 1.240(13) 0.879(4) 0.033(19) Uiso 1 1 d . . . . .
C7 C 0.3930(4) 0.9935(9) 0.7934(4) 0.0241(13) Uani 1 1 d . . . . .
H7 H 0.451537 1.080909 0.782701 0.029 Uiso 1 1 calc R U . . .
N8 N 0.4287(3) 0.7715(8) 0.8492(3) 0.0249(11) Uani 1 1 d . . . . .
C9 C 0.4010(4) 0.7561(11) 0.9303(4) 0.0250(13) Uani 1 1 d . . . . .
O10 O 0.4192(3) 0.5870(7) 0.9871(3) 0.0313(10) Uani 1 1 d . . . . .
N11 N 0.4884(3) 0.5925(8) 0.8285(3) 0.0255(11) Uani 1 1 d . . . . .
C12 C 0.5122(4) 0.6117(11) 0.7516(4) 0.0281(13) Uani 1 1 d . . . . .
H12 H 0.487214 0.745134 0.709507 0.034 Uiso 1 1 calc R U . . .
C13 C 0.5774(4) 0.4301(11) 0.7280(4) 0.0292(14) Uani 1 1 d . . . . .
C14 C 0.5865(5) 0.4168(12) 0.6361(4) 0.0369(16) Uani 1 1 d . . . . .
H14 H 0.550976 0.530809 0.588967 0.044 Uiso 1 1 calc R U . . .
C15 C 0.6461(5) 0.2413(13) 0.6122(4) 0.0394(16) Uani 1 1 d . . . . .
H15 H 0.649740 0.232200 0.548851 0.047 Uiso 1 1 calc R U . . .
C16 C 0.7001(5) 0.0802(11) 0.6805(4) 0.0328(14) Uani 1 1 d . . . . .
C17 C 0.6927(4) 0.0898(12) 0.7726(4) 0.0348(15) Uani 1 1 d . . . . .
H17 H 0.729654 -0.022477 0.819663 0.042 Uiso 1 1 calc R U . . .
C18 C 0.6320(4) 0.2612(11) 0.7953(4) 0.0309(14) Uani 1 1 d . . . . .
H18 H 0.627023 0.265133 0.858284 0.037 Uiso 1 1 calc R U . . .
O19 O 0.7591(4) -0.0843(8) 0.6517(3) 0.0459(12) Uani 1 1 d . . . . .
C20 C 0.8170(5) -0.2528(14) 0.7210(5) 0.0486(18) Uani 1 1 d . . . . .
H20A H 0.860117 -0.162080 0.775886 0.073 Uiso 1 1 calc R U . . .
H20B H 0.858987 -0.352111 0.692682 0.073 Uiso 1 1 calc R U . . .
H20C H 0.771712 -0.360184 0.742228 0.073 Uiso 1 1 calc R U . . .
C21 C 0.3154(4) 0.9437(10) 0.6983(4) 0.0266(13) Uani 1 1 d . . . . .
C22 C 0.2529(4) 0.7390(10) 0.6795(4) 0.0290(14) Uani 1 1 d . . . . .
H22 H 0.261082 0.617371 0.727498 0.035 Uiso 1 1 calc R U . . .
C23 C 0.1786(4) 0.7080(11) 0.5921(4) 0.0321(15) Uani 1 1 d . . . . .
H23 H 0.135523 0.569099 0.581082 0.039 Uiso 1 1 calc R U . . .
C24 C 0.1686(5) 0.8816(11) 0.5221(4) 0.0311(14) Uani 1 1 d . . . . .
C25 C 0.2317(5) 1.0822(11) 0.5384(4) 0.0348(15) Uani 1 1 d . . . . .
H25 H 0.225162 1.200513 0.489505 0.042 Uiso 1 1 calc R U . . .
C26 C 0.3034(5) 1.1107(11) 0.6248(4) 0.0316(14) Uani 1 1 d . . . . .
H26 H 0.346549 1.249521 0.634778 0.038 Uiso 1 1 calc R U . . .
O27 O 0.0964(3) 0.8731(8) 0.4330(3) 0.0435(12) Uani 1 1 d . . . . .
C28 C 0.0303(5) 0.6681(13) 0.4129(5) 0.0487(19) Uani 1 1 d . . . . .
H28A H 0.069577 0.516947 0.418282 0.073 Uiso 1 1 calc R U . . .
H28B H -0.016132 0.682589 0.347865 0.073 Uiso 1 1 calc R U . . .
H28C H -0.008153 0.663654 0.458508 0.073 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
C1 C3 1.524(10) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.483(10) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.534(9) . ?
C3 H3 1.0000 . ?
C4 C5 1.529(8) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N6 1.472(7) . ?
C5 C9 1.509(8) . ?
C5 H5 1.0000 . ?
N6 C7 1.471(7) . ?
N6 H6A 0.79(7) . ?
C7 N8 1.462(7) . ?
C7 C21 1.508(8) . ?
C7 H7 1.0000 . ?
N8 C9 1.366(6) . ?
N8 N11 1.376(6) . ?
C9 O10 1.218(6) . ?
N11 C12 1.278(6) . ?
C12 C13 1.458(8) . ?
C12 H12 0.9500 . ?
C13 C18 1.396(8) . ?
C13 C14 1.398(7) . ?
C14 C15 1.382(9) . ?
C14 H14 0.9500 . ?
C15 C16 1.373(9) . ?
C15 H15 0.9500 . ?
C16 O19 1.370(7) . ?
C16 C17 1.390(8) . ?
C17 C18 1.370(8) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
O19 C20 1.426(8) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C26 1.384(8) . ?
C21 C22 1.392(8) . ?
C22 C23 1.392(7) . ?
C22 H22 0.9500 . ?
C23 C24 1.374(8) . ?
C23 H23 0.9500 . ?
C24 C25 1.378(8) . ?
C24 O27 1.387(7) . ?
C25 C26 1.365(8) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
O27 C28 1.422(7) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 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
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C2 C3 C1 111.5(7) . . ?
C2 C3 C4 111.1(6) . . ?
C1 C3 C4 109.6(7) . . ?
C2 C3 H3 108.2 . . ?
C1 C3 H3 108.2 . . ?
C4 C3 H3 108.2 . . ?
C5 C4 C3 113.8(5) . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
N6 C5 C9 105.6(4) . . ?
N6 C5 C4 113.0(5) . . ?
C9 C5 C4 110.6(4) . . ?
N6 C5 H5 109.2 . . ?
C9 C5 H5 109.2 . . ?
C4 C5 H5 109.2 . . ?
C7 N6 C5 107.9(4) . . ?
C7 N6 H6A 105(5) . . ?
C5 N6 H6A 110(4) . . ?
N8 C7 N6 103.7(4) . . ?
N8 C7 C21 113.3(4) . . ?
N6 C7 C21 112.1(4) . . ?
N8 C7 H7 109.2 . . ?
N6 C7 H7 109.2 . . ?
C21 C7 H7 109.2 . . ?
C9 N8 N11 120.1(4) . . ?
C9 N8 C7 113.7(4) . . ?
N11 N8 C7 126.1(4) . . ?
O10 C9 N8 126.2(5) . . ?
O10 C9 C5 127.5(5) . . ?
N8 C9 C5 106.3(5) . . ?
C12 N11 N8 118.5(5) . . ?
N11 C12 C13 120.4(5) . . ?
N11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C18 C13 C14 117.4(5) . . ?
C18 C13 C12 121.6(5) . . ?
C14 C13 C12 121.0(5) . . ?
C15 C14 C13 121.4(6) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C16 C15 C14 119.7(5) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
O19 C16 C15 116.1(5) . . ?
O19 C16 C17 123.9(6) . . ?
C15 C16 C17 120.0(5) . . ?
C18 C17 C16 120.0(6) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C13 121.4(5) . . ?
C17 C18 H18 119.3 . . ?
C13 C18 H18 119.3 . . ?
C16 O19 C20 117.6(5) . . ?
O19 C20 H20A 109.5 . . ?
O19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C26 C21 C22 117.0(5) . . ?
C26 C21 C7 119.1(5) . . ?
C22 C21 C7 123.8(5) . . ?
C21 C22 C23 121.7(5) . . ?
C21 C22 H22 119.2 . . ?
C23 C22 H22 119.2 . . ?
C24 C23 C22 119.0(6) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C23 C24 C25 120.2(5) . . ?
C23 C24 O27 124.2(6) . . ?
C25 C24 O27 115.5(5) . . ?
C26 C25 C24 120.0(6) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C21 122.0(6) . . ?
C25 C26 H26 119.0 . . ?
C21 C26 H26 119.0 . . ?
C24 O27 C28 117.4(5) . . ?
O27 C28 H28A 109.5 . . ?
O27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

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
N6 H6A O10 0.79(7) 2.43(7) 3.059(6) 137(6) 1_565 yes
N6 H6A N11 0.79(7) 2.56(7) 3.207(7) 140(5) 1_565 yes
C20 H20B O27 0.98 2.60 3.527(8) 157.8 2_636 yes
C25 H25 O19 0.95 2.45 3.372(7) 162.5 2_666 yes

_refine_diff_density_max         0.230
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.053

