# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_y
_database_code_depnum_ccdc_archive 'CCDC 2247417'
loop_
_audit_author_name
_audit_author_address
'xiao geng'
;Taizhou University
China
;
_audit_update_record             
;
2023-03-09 deposited with the CCDC.	2023-10-20 downloaded from the CCDC.
;
_audit_creation_date             2023-03-09
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H17 N3 O3'
_chemical_formula_sum            'C15 H17 N3 O3'
_chemical_formula_weight         287.32
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9139(16)
_cell_length_b                   10.160(2)
_cell_length_c                   11.688(3)
_cell_angle_alpha                112.767(3)
_cell_angle_beta                 91.686(3)
_cell_angle_gamma                91.806(3)
_cell_volume                     755.9(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4061
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.15
_cell_measurement_theta_min      2.95
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.6654
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.887
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8092
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.079
_diffrn_reflns_theta_min         1.892
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.887
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3402
_reflns_number_total             4688
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.097(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         4688
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0493
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0999P)²+0.0339P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1492
_refine_ls_wR_factor_ref         0.1679
_refine_special_details          ?
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups 
2.a Secondary CH2 refined with riding coordinates: 
 C14(H14A,H14B) 
2.b Aromatic/amide H refined with riding coordinates: 
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10) 
2.c Idealised Me refined as rotating group: 
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C15(H15A,H15B,H15C) 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
; 
The structure was solved using Direct Methods (ShelXS). RE = 0.3, Nqual =  -1, Ralpha = 0.035 
;
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 0.39385(11) 0.86242(7) 0.76250(7) 0.0421(2) Uani 1 1 d . . . . .
O2 O 0.33766(17) 0.64960(12) 1.02480(9) 0.0688(3) Uani 1 1 d . . . . .
O3 O 0.16290(14) 0.77397(11) 0.93924(9) 0.0593(3) Uani 1 1 d . . . . .
N1 N 0.25769(17) 0.74001(11) 0.57735(10) 0.0535(3) Uani 1 1 d . . . . .
N2 N 0.29503(17) 0.64572(10) 0.63674(9) 0.0520(3) Uani 1 1 d . . . . .
N3 N 0.73892(15) 0.55797(11) 0.75620(9) 0.0482(2) Uani 1 1 d . . . . .
C1 C 0.31166(14) 1.00121(11) 0.64064(11) 0.0419(2) Uani 1 1 d . . . . .
C2 C 0.25166(19) 1.00421(14) 0.52700(13) 0.0531(3) Uani 1 1 d . . . . .
H2 H 0.2172 0.9196 0.4599 0.064 Uiso 1 1 calc R . . . .
C3 C 0.2436(2) 1.13335(16) 0.51442(15) 0.0643(4) Uani 1 1 d . . . . .
H3 H 0.2033 1.1353 0.4385 0.077 Uiso 1 1 calc R . . . .
C4 C 0.2943(2) 1.25919(15) 0.61249(17) 0.0674(4) Uani 1 1 d . . . . .
H4 H 0.2893 1.3457 0.6029 0.081 Uiso 1 1 calc R . . . .
C5 C 0.3527(2) 1.25639(14) 0.72524(17) 0.0696(4) Uani 1 1 d . . . . .
H5 H 0.3857 1.3416 0.7921 0.083 Uiso 1 1 calc R . . . .
C6 C 0.3626(2) 1.12786(13) 0.73994(14) 0.0560(3) Uani 1 1 d . . . . .
H6 H 0.4031 1.1266 0.8161 0.067 Uiso 1 1 calc R . . . .
C7 C 0.31783(15) 0.86501(11) 0.65492(10) 0.0398(2) Uani 1 1 d . . . . .
C8 C 0.37491(16) 0.72089(10) 0.74379(10) 0.0398(2) Uani 1 1 d . . . . .
C9 C 0.43920(16) 0.67242(11) 0.84046(10) 0.0419(2) Uani 1 1 d . . . . .
C10 C 0.59670(17) 0.59104(11) 0.83432(10) 0.0427(2) Uani 1 1 d . . . . .
H10 H 0.6045 0.5531 0.8950 0.051 Uiso 1 1 calc R . . . .
C11 C 0.7651(2) 0.61531(16) 0.66165(13) 0.0605(3) Uani 1 1 d . . . . .
H11A H 0.6828 0.5619 0.5899 0.091 Uiso 1 1 calc GR . . . .
H11B H 0.8979 0.6083 0.6389 0.091 Uiso 1 1 calc GR . . . .
H11C H 0.7321 0.7137 0.6934 0.091 Uiso 1 1 calc GR . . . .
C12 C 0.8785(2) 0.45482(16) 0.75879(15) 0.0653(4) Uani 1 1 d . . . . .
H12A H 0.8514 0.4244 0.8251 0.098 Uiso 1 1 calc GR . . . .
H12B H 1.0069 0.4983 0.7718 0.098 Uiso 1 1 calc GR . . . .
H12C H 0.8694 0.3737 0.6811 0.098 Uiso 1 1 calc GR . . . .
C13 C 0.31497(18) 0.69495(13) 0.94374(11) 0.0480(3) Uani 1 1 d . . . . .
C14 C 0.0345(2) 0.81099(19) 1.04159(15) 0.0718(4) Uani 1 1 d . . . . .
H14A H 0.0173 0.7305 1.0660 0.086 Uiso 1 1 calc R . . . .
H14B H -0.0913 0.8313 1.0149 0.086 Uiso 1 1 calc R . . . .
C15 C 0.1129(3) 0.9376(3) 1.1500(2) 0.1087(8) Uani 1 1 d . . . . .
H15A H 0.1417 1.0147 1.1241 0.163 Uiso 1 1 calc GR . . . .
H15B H 0.2291 0.9136 1.1831 0.163 Uiso 1 1 calc GR . . . .
H15C H 0.0186 0.9662 1.2127 0.163 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 C7 1.3585(13) . ?
O1 C8 1.3695(12) . ?
O2 C13 1.2116(14) . ?
O3 C13 1.3548(15) . ?
O3 C14 1.4478(17) . ?
N1 N2 1.4092(14) . ?
N1 C7 1.2888(15) . ?
N2 C8 1.2833(15) . ?
N3 C10 1.3227(16) . ?
N3 C11 1.4480(16) . ?
N3 C12 1.4552(16) . ?
C1 C2 1.3917(17) . ?
C1 C6 1.3850(18) . ?
C1 C7 1.4583(14) . ?
C2 H2 0.9300 . ?
C2 C3 1.3782(17) . ?
C3 H3 0.9300 . ?
C3 C4 1.373(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.3849(18) . ?
C6 H6 0.9300 . ?
C8 C9 1.4600(14) . ?
C9 C10 1.3747(16) . ?
C9 C13 1.4514(17) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.486(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C7 O1 C8 103.16(8) . . ?
C13 O3 C14 116.64(11) . . ?
C7 N1 N2 105.92(9) . . ?
C8 N2 N1 106.97(9) . . ?
C10 N3 C11 124.12(10) . . ?
C10 N3 C12 120.44(10) . . ?
C11 N3 C12 115.42(11) . . ?
C2 C1 C7 119.82(11) . . ?
C6 C1 C2 119.74(11) . . ?
C6 C1 C7 120.43(11) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.61(13) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.89(14) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.55(12) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.58(14) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 120.2 . . ?
C5 C6 C1 119.63(13) . . ?
C5 C6 H6 120.2 . . ?
O1 C7 C1 119.07(9) . . ?
N1 C7 O1 112.37(9) . . ?
N1 C7 C1 128.56(10) . . ?
O1 C8 C9 120.52(9) . . ?
N2 C8 O1 111.59(9) . . ?
N2 C8 C9 127.89(10) . . ?
C10 C9 C8 125.00(10) . . ?
C10 C9 C13 116.47(10) . . ?
C13 C9 C8 118.02(10) . . ?
N3 C10 C9 130.51(10) . . ?
N3 C10 H10 114.7 . . ?
C9 C10 H10 114.7 . . ?
N3 C11 H11A 109.5 . . ?
N3 C11 H11B 109.5 . . ?
N3 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
N3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 O3 122.33(11) . . ?
O2 C13 C9 126.23(11) . . ?
O3 C13 C9 111.43(10) . . ?
O3 C14 H14A 109.4 . . ?
O3 C14 H14B 109.4 . . ?
O3 C14 C15 111.28(14) . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
