# Supplementary Information (SI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_240124_l7m2142_p
_database_code_depnum_ccdc_archive 'CCDC 2329040'
loop_
_audit_author_name
_audit_author_address
'Mao Yihui'
;Zhejiang University
China
;
_audit_update_record             
;
2024-01-29 deposited with the CCDC.	2024-12-13 downloaded from the CCDC.
;
_audit_creation_date             2024-01-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H21 N O4'
_chemical_formula_sum            'C17 H21 N O4'
_chemical_formula_weight         303.35
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.2627(5)
_cell_length_b                   8.4254(4)
_cell_length_c                   16.0986(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.5900(10)
_cell_angle_gamma                90
_cell_volume                     1629.36(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9555
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      28.262
_cell_measurement_theta_min      2.741
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1496 before and 0.0561 after correction.
The Ratio of minimum to maximum transmission is 0.9120.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            22684
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.342
_diffrn_reflns_theta_min         2.583
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3342
_reflns_number_total             4056
_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 V8.40B (?, 2016)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         4056
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.092
_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)+(0.0330P)²+0.6272P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1046
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C15(H15A,H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.04727(9) 0.64916(13) 0.44039(7) 0.0415(3) Uani 1 1 d . . . . .
N1 N 0.39888(8) 0.89195(13) 0.42266(6) 0.0263(2) Uani 1 1 d . . . . .
H1 H 0.392644 0.940582 0.469860 0.032 Uiso 1 1 calc R U . . .
C1 C 0.11501(11) 0.96770(17) 0.59400(8) 0.0322(3) Uani 1 1 d . . . . .
H1A H 0.172476 1.017536 0.571769 0.039 Uiso 1 1 calc R U . . .
O2 O 0.18089(7) 0.83606(11) 0.45705(6) 0.0312(2) Uani 1 1 d . . . . .
C2 C 0.08206(13) 1.02965(19) 0.66464(9) 0.0395(3) Uani 1 1 d . . . . .
H2 H 0.116719 1.123010 0.690595 0.047 Uiso 1 1 calc R U . . .
O3 O 0.58245(7) 0.94915(12) 0.42077(6) 0.0321(2) Uani 1 1 d . . . . .
C3 C -0.00078(14) 0.9570(2) 0.69781(10) 0.0468(4) Uani 1 1 d . . . . .
H3 H -0.022404 0.999519 0.746729 0.056 Uiso 1 1 calc R U . . .
O4 O 0.47602(7) 0.80620(11) 0.31789(5) 0.0277(2) Uani 1 1 d . . . . .
C4 C -0.05196(14) 0.8224(2) 0.65948(11) 0.0484(4) Uani 1 1 d . . . . .
H4 H -0.109350 0.773163 0.682085 0.058 Uiso 1 1 calc R U . . .
C5 C -0.02086(12) 0.75798(19) 0.58853(10) 0.0393(3) Uani 1 1 d . . . . .
H5 H -0.056242 0.665075 0.562598 0.047 Uiso 1 1 calc R U . . .
C6 C 0.06324(11) 0.83172(16) 0.55578(8) 0.0298(3) Uani 1 1 d . . . . .
C7 C 0.09328(10) 0.76027(16) 0.47927(8) 0.0291(3) Uani 1 1 d . . . . .
C8 C 0.21277(11) 0.77850(17) 0.38419(8) 0.0307(3) Uani 1 1 d . . . . .
H8 H 0.162109 0.717820 0.344110 0.037 Uiso 1 1 calc R U . . .
C9 C 0.31329(10) 0.80867(15) 0.37127(8) 0.0256(3) Uani 1 1 d . . . . .
C10 C 0.49315(10) 0.88885(15) 0.39096(7) 0.0255(3) Uani 1 1 d . . . . .
C11 C 0.36081(10) 0.74639(16) 0.29746(8) 0.0264(3) Uani 1 1 d . . . . .
C12 C 0.36515(11) 0.56545(16) 0.29735(8) 0.0299(3) Uani 1 1 d . . . . .
H12A H 0.288024 0.524234 0.283401 0.036 Uiso 1 1 calc R U . . .
H12B H 0.403433 0.530636 0.251888 0.036 Uiso 1 1 calc R U . . .
C13 C 0.42410(12) 0.49152(17) 0.38076(9) 0.0354(3) Uani 1 1 d . . . . .
H13A H 0.504027 0.519928 0.391182 0.042 Uiso 1 1 calc R U . . .
H13B H 0.392354 0.535857 0.427697 0.042 Uiso 1 1 calc R U . . .
C14 C 0.41270(16) 0.31196(19) 0.38041(11) 0.0497(4) Uani 1 1 d . . . . .
H14A H 0.439432 0.268084 0.331775 0.075 Uiso 1 1 calc R U . . .
H14B H 0.334320 0.283363 0.376238 0.075 Uiso 1 1 calc R U . . .
H14C H 0.456992 0.268613 0.433003 0.075 Uiso 1 1 calc R U . . .
C15 C 0.30437(11) 0.81512(16) 0.21191(8) 0.0307(3) Uani 1 1 d . . . . .
H15A H 0.341950 0.772176 0.167753 0.037 Uiso 1 1 calc R U . . .
H15B H 0.226208 0.777956 0.198735 0.037 Uiso 1 1 calc R U . . .
C16 C 0.30474(12) 0.99567(18) 0.20658(9) 0.0355(3) Uani 1 1 d . . . . .
H16A H 0.382618 1.034063 0.219510 0.043 Uiso 1 1 calc R U . . .
H16B H 0.266129 1.039788 0.249846 0.043 Uiso 1 1 calc R U . . .
C17 C 0.24783(14) 1.0561(2) 0.11926(11) 0.0490(4) Uani 1 1 d . . . . .
H17A H 0.281880 1.006094 0.075737 0.074 Uiso 1 1 calc R U . . .
H17B H 0.256610 1.171547 0.116906 0.074 Uiso 1 1 calc R U . . .
H17C H 0.168448 1.029554 0.109043 0.074 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 C7 1.2019(16) . ?
N1 H1 0.8800 . ?
N1 C9 1.3891(15) . ?
N1 C10 1.3544(16) . ?
C1 H1A 0.9500 . ?
C1 C2 1.3832(19) . ?
C1 C6 1.392(2) . ?
O2 C7 1.3579(15) . ?
O2 C8 1.3959(15) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(2) . ?
O3 C10 1.2152(15) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(3) . ?
O4 C10 1.3467(14) . ?
O4 C11 1.4736(14) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.3950(19) . ?
C6 C7 1.4825(18) . ?
C8 H8 0.9500 . ?
C8 C9 1.3154(18) . ?
C9 C11 1.5181(17) . ?
C11 C12 1.5255(18) . ?
C11 C15 1.5259(17) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.5244(19) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.519(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.524(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.526(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C9 N1 H1 124.3 . . ?
C10 N1 H1 124.3 . . ?
C10 N1 C9 111.45(10) . . ?
C2 C1 H1A 120.3 . . ?
C2 C1 C6 119.44(14) . . ?
C6 C1 H1A 120.3 . . ?
C7 O2 C8 115.33(10) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.62(15) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.64(14) . . ?
C4 C3 H3 120.2 . . ?
C10 O4 C11 110.25(9) . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 120.97(15) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 118.95(15) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C5 120.38(13) . . ?
C1 C6 C7 122.29(12) . . ?
C5 C6 C7 117.33(13) . . ?
O1 C7 O2 122.86(12) . . ?
O1 C7 C6 125.44(12) . . ?
O2 C7 C6 111.69(11) . . ?
O2 C8 H8 120.2 . . ?
C9 C8 O2 119.69(11) . . ?
C9 C8 H8 120.2 . . ?
N1 C9 C11 106.13(10) . . ?
C8 C9 N1 128.56(11) . . ?
C8 C9 C11 125.18(11) . . ?
O3 C10 N1 127.79(11) . . ?
O3 C10 O4 122.09(11) . . ?
O4 C10 N1 110.12(10) . . ?
O4 C11 C9 102.04(9) . . ?
O4 C11 C12 108.05(10) . . ?
O4 C11 C15 108.20(10) . . ?
C9 C11 C12 111.43(11) . . ?
C9 C11 C15 113.55(11) . . ?
C12 C11 C15 112.82(10) . . ?
C11 C12 H12A 108.6 . . ?
C11 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C13 C12 C11 114.69(11) . . ?
C13 C12 H12A 108.6 . . ?
C13 C12 H12B 108.6 . . ?
C12 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 C12 112.13(12) . . ?
C14 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 H15A 108.5 . . ?
C11 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
C16 C15 C11 115.07(11) . . ?
C16 C15 H15A 108.5 . . ?
C16 C15 H15B 108.5 . . ?
C15 C16 H16A 109.1 . . ?
C15 C16 H16B 109.1 . . ?
C15 C16 C17 112.28(12) . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
N1 C9 C11 O4 0.17(13) . . . . ?
N1 C9 C11 C12 115.26(11) . . . . ?
N1 C9 C11 C15 -116.02(12) . . . . ?
C1 C2 C3 C4 -0.7(2) . . . . ?
C1 C6 C7 O1 -175.18(13) . . . . ?
C1 C6 C7 O2 4.76(17) . . . . ?
O2 C8 C9 N1 1.2(2) . . . . ?
O2 C8 C9 C11 176.59(11) . . . . ?
C2 C1 C6 C5 -0.26(19) . . . . ?
C2 C1 C6 C7 179.13(12) . . . . ?
C2 C3 C4 C5 0.6(2) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
O4 C11 C12 C13 58.60(14) . . . . ?
O4 C11 C15 C16 -56.52(14) . . . . ?
C4 C5 C6 C1 0.1(2) . . . . ?
C4 C5 C6 C7 -179.34(13) . . . . ?
C5 C6 C7 O1 4.2(2) . . . . ?
C5 C6 C7 O2 -175.83(11) . . . . ?
C6 C1 C2 C3 0.6(2) . . . . ?
C7 O2 C8 C9 -159.74(12) . . . . ?
C8 O2 C7 O1 1.49(18) . . . . ?
C8 O2 C7 C6 -178.45(10) . . . . ?
C8 C9 C11 O4 -176.05(13) . . . . ?
C8 C9 C11 C12 -60.96(17) . . . . ?
C8 C9 C11 C15 67.76(17) . . . . ?
C9 N1 C10 O3 -179.57(13) . . . . ?
C9 N1 C10 O4 0.46(15) . . . . ?
C9 C11 C12 C13 -52.72(15) . . . . ?
C9 C11 C15 C16 56.00(15) . . . . ?
C10 N1 C9 C8 175.67(14) . . . . ?
C10 N1 C9 C11 -0.38(14) . . . . ?
C10 O4 C11 C9 0.09(13) . . . . ?
C10 O4 C11 C12 -117.45(11) . . . . ?
C10 O4 C11 C15 120.10(11) . . . . ?
C11 O4 C10 N1 -0.33(14) . . . . ?
C11 O4 C10 O3 179.70(12) . . . . ?
C11 C12 C13 C14 172.61(13) . . . . ?
C11 C15 C16 C17 179.57(12) . . . . ?
C12 C11 C15 C16 -176.00(11) . . . . ?
C15 C11 C12 C13 178.17(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
