# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_zhzhw_1010_auto
_database_code_depnum_ccdc_archive 'CCDC 2209775'
loop_
_audit_author_name
_audit_author_address
'Hang and Zhi-Wei'
;Hebei University of Science and Technology
China
;
_audit_update_record             
;
2022-09-27 deposited with the CCDC.	2022-11-24 downloaded from the CCDC.
;
_audit_creation_date             2021-10-10
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H26 N2 O6'
_chemical_formula_sum            'C23 H26 N2 O6'
_chemical_formula_weight         426.46
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   8.6271(4)
_cell_length_b                   11.5365(6)
_cell_length_c                   12.0186(8)
_cell_angle_alpha                112.233(6)
_cell_angle_beta                 90.786(5)
_cell_angle_gamma                95.430(4)
_cell_volume                     1100.68(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1934
_cell_measurement_temperature    292.8(2)
_cell_measurement_theta_max      75.1880
_cell_measurement_theta_min      3.9450
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.941
_exptl_absorpt_coefficient_mu    0.773
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13568
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.434
_diffrn_reflns_theta_min         3.979
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.8(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -98.00 -60.00   1.00    0.20    --  -47.57 142.00-123.00   38
  2  ω    -95.00 -29.00   1.00    0.20    --  -47.57 127.00  66.00   66
  3  ω     38.00 112.00   1.00    0.20    --   47.57  77.00  60.00   74
  4  ω     98.00 154.00   1.00    0.61    --  107.75  57.00 -30.00   56
  5  ω    127.00 171.00   1.00    0.61    --  107.75  37.00-120.00   44
  6  ω    -65.00 -28.00   1.00    0.61    -- -100.00  57.00  60.00   37
  7  ω   -102.00 -28.00   1.00    0.61    -- -100.00  77.00 -30.00   74
  8  ω     41.00  67.00   1.00    0.20    --   47.57-142.00-179.00   26
  9  ω     55.00  80.00   1.00    0.61    --  107.75-142.00-179.00   25
 10  ω     38.00 107.00   1.00    0.61    --  107.75-125.00-180.00   69
 11  ω     73.00 102.00   1.00    0.61    --  107.75 -99.00-150.00   29
 12  ω     74.00 100.00   1.00    0.61    --  107.75 -99.00-120.00   26
 13  ω     68.00  94.00   1.00    0.61    --  107.75-127.00  -9.00   26
 14  ω     39.00  65.00   1.00    0.61    --  107.75 -99.00-120.00   26
 15  ω     33.00  58.00   1.00    0.20    --   47.57-127.00  -9.00   25
 16  ω     66.00  92.00   1.00    0.61    --  107.75 -99.00   0.00   26
 17  ω     62.00  88.00   1.00    0.61    --  107.75 -77.00   0.00   26
 18  ω     35.00  60.00   1.00    0.61    --  107.75 -57.00  30.00   25
 19  ω     36.00  62.00   1.00    0.61    --  107.75 -57.00  60.00   26
 20  ω     35.00  61.00   1.00    0.61    --  107.75 -57.00 120.00   26
 21  ω    -26.00  19.00   1.00    0.20    --   47.57 -19.00  90.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0470618000
_diffrn_orient_matrix_UB_12      0.0058675000
_diffrn_orient_matrix_UB_13      -0.1217407000
_diffrn_orient_matrix_UB_21      0.0480764000
_diffrn_orient_matrix_UB_22      -0.1332692000
_diffrn_orient_matrix_UB_23      -0.0660069000
_diffrn_orient_matrix_UB_31      -0.1666048000
_diffrn_orient_matrix_UB_32      -0.0570099000
_diffrn_orient_matrix_UB_33      0.0073104000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3095
_reflns_number_total             4395
_reflns_odcompleteness_completeness 76.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4395
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0624
_refine_ls_restrained_S_all      1.057
_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)+(0.0838P)²+0.2581P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1739
_refine_ls_wR_factor_ref         0.1903
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C3(H3A), C6(H6), C17(H17), C19(H19), C20(H20), C22(H22)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C12(H12A,H12B,H12C), C23(H23A,H23B,H23C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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 1.0554(3) 0.7689(2) 0.42707(19) 0.0996(7) Uani 1 1 d . . . . .
O2 O 1.0369(2) 0.6008(2) 0.25982(17) 0.0917(6) Uani 1 1 d . . . . .
O3 O 0.7184(2) 0.26053(15) 0.32231(15) 0.0811(5) Uani 1 1 d . . . . .
H3 H 0.651326 0.228324 0.352592 0.122 Uiso 1 1 calc GR . . . .
O4 O 0.5439(2) 0.25143(15) 0.49701(16) 0.0764(5) Uani 1 1 d . . . . .
O5 O 0.53797(18) 0.42621(14) 0.66151(14) 0.0668(4) Uani 1 1 d . . . . .
O6 O 0.2352(3) 1.0983(2) 0.7256(3) 0.1105(7) Uani 1 1 d . . . . .
N1 N 0.8726(2) 0.76794(18) 0.60412(18) 0.0726(6) Uani 1 1 d . . . . .
H1 H 0.941949 0.810045 0.579515 0.087 Uiso 1 1 calc R . . . .
N2 N 0.7069(4) 1.1519(2) 1.0558(2) 0.0921(8) Uani 1 1 d . . . . .
H2 H 0.716348 1.188412 1.132907 0.111 Uiso 1 1 calc R . . . .
C1 C 0.8361(2) 0.6426(2) 0.5355(2) 0.0578(5) Uani 1 1 d . . . . .
C2 C 0.8985(2) 0.5848(2) 0.4213(2) 0.0582(5) Uani 1 1 d . . . . .
C3 C 0.8573(3) 0.4577(2) 0.3545(2) 0.0628(5) Uani 1 1 d . . . . .
H3A H 0.899929 0.420478 0.280246 0.075 Uiso 1 1 calc R . . . .
C4 C 0.7546(3) 0.3848(2) 0.3951(2) 0.0603(5) Uani 1 1 d . . . . .
C5 C 0.6924(2) 0.44006(19) 0.50693(19) 0.0551(5) Uani 1 1 d . . . . .
C6 C 0.7339(2) 0.5673(2) 0.5757(2) 0.0577(5) Uani 1 1 d . . . . .
H6 H 0.692320 0.603199 0.650568 0.069 Uiso 1 1 calc R . . . .
C7 C 1.0037(3) 0.6612(2) 0.3722(2) 0.0677(6) Uani 1 1 d . . . . .
C8 C 1.1324(5) 0.6763(4) 0.2062(3) 0.1132(12) Uani 1 1 d . . . . .
H8A H 1.071759 0.738402 0.195697 0.136 Uiso 1 1 calc R . . . .
H8B H 1.222211 0.720623 0.259931 0.136 Uiso 1 1 calc R . . . .
C9 C 1.1817(7) 0.6008(5) 0.0966(4) 0.167(2) Uani 1 1 d . . . . .
H9A H 1.097460 0.578279 0.036745 0.251 Uiso 1 1 calc GR . . . .
H9B H 1.214676 0.525925 0.102117 0.251 Uiso 1 1 calc GR . . . .
H9C H 1.267360 0.645656 0.074468 0.251 Uiso 1 1 calc GR . . . .
C10 C 0.5855(3) 0.3629(2) 0.5528(2) 0.0590(5) Uani 1 1 d . . . . .
C11 C 0.4340(3) 0.3562(2) 0.7141(2) 0.0719(6) Uani 1 1 d . . . . .
H11A H 0.486109 0.290286 0.725521 0.086 Uiso 1 1 calc R . . . .
H11B H 0.341487 0.317637 0.661529 0.086 Uiso 1 1 calc R . . . .
C12 C 0.3904(4) 0.4480(3) 0.8329(3) 0.0924(9) Uani 1 1 d . . . . .
H12A H 0.333830 0.509993 0.820046 0.139 Uiso 1 1 calc GR . . . .
H12B H 0.483221 0.488752 0.882534 0.139 Uiso 1 1 calc GR . . . .
H12C H 0.326285 0.403962 0.872119 0.139 Uiso 1 1 calc GR . . . .
C13 C 0.8018(3) 0.8330(2) 0.7148(2) 0.0687(6) Uani 1 1 d . . . . .
H13A H 0.832643 0.801541 0.775141 0.082 Uiso 1 1 calc R . . . .
H13B H 0.689187 0.817525 0.702290 0.082 Uiso 1 1 calc R . . . .
C14 C 0.8517(3) 0.9734(2) 0.7587(2) 0.0737(7) Uani 1 1 d . . . . .
H14A H 0.962809 0.989088 0.779568 0.088 Uiso 1 1 calc R . . . .
H14B H 0.832309 1.002323 0.694287 0.088 Uiso 1 1 calc R . . . .
C15 C 0.7661(3) 1.0467(2) 0.8662(2) 0.0710(6) Uani 1 1 d . . . . .
C16 C 0.6096(3) 1.0777(2) 0.8655(2) 0.0669(6) Uani 1 1 d . . . . .
C17 C 0.4958(3) 1.0585(2) 0.7735(2) 0.0732(7) Uani 1 1 d . . . . .
H17 H 0.515350 1.015032 0.693211 0.088 Uiso 1 1 calc R . . . .
C18 C 0.3542(4) 1.1055(3) 0.8050(3) 0.0878(8) Uani 1 1 d . . . . .
C19 C 0.3246(4) 1.1691(3) 0.9269(4) 0.1012(10) Uani 1 1 d . . . . .
H19 H 0.228019 1.198703 0.946485 0.121 Uiso 1 1 calc R . . . .
C20 C 0.4331(5) 1.1885(3) 1.0164(3) 0.0962(10) Uani 1 1 d . . . . .
H20 H 0.411922 1.230965 1.096515 0.115 Uiso 1 1 calc R . . . .
C21 C 0.5763(4) 1.1435(2) 0.9861(2) 0.0786(8) Uani 1 1 d . . . . .
C22 C 0.8197(4) 1.0934(3) 0.9837(3) 0.0855(8) Uani 1 1 d . . . . .
H22 H 0.918591 1.086419 1.010681 0.103 Uiso 1 1 calc R . . . .
C23 C 0.2535(5) 1.0340(3) 0.6016(4) 0.1176(12) Uani 1 1 d . . . . .
H23A H 0.160526 1.034252 0.556920 0.176 Uiso 1 1 calc GR . . . .
H23B H 0.271971 0.948731 0.586374 0.176 Uiso 1 1 calc GR . . . .
H23C H 0.340490 1.075381 0.577137 0.176 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 1.201(3) . ?
O2 C7 1.315(3) . ?
O2 C8 1.468(3) . ?
O3 C4 1.370(3) . ?
O4 C10 1.219(3) . ?
O5 C10 1.326(3) . ?
O5 C11 1.457(3) . ?
O6 C18 1.367(4) . ?
O6 C23 1.410(4) . ?
N1 C1 1.369(3) . ?
N1 C13 1.435(3) . ?
N2 C21 1.368(4) . ?
N2 C22 1.363(4) . ?
C1 C2 1.419(3) . ?
C1 C6 1.396(3) . ?
C2 C3 1.387(3) . ?
C2 C7 1.485(3) . ?
C3 C4 1.383(3) . ?
C4 C5 1.392(3) . ?
C5 C6 1.393(3) . ?
C5 C10 1.475(3) . ?
C8 C9 1.375(5) . ?
C11 C12 1.499(4) . ?
C13 C14 1.518(3) . ?
C14 C15 1.499(3) . ?
C15 C16 1.429(4) . ?
C15 C22 1.363(4) . ?
C16 C17 1.407(4) . ?
C16 C21 1.407(3) . ?
C17 C18 1.383(4) . ?
C18 C19 1.408(5) . ?
C19 C20 1.354(5) . ?
C20 C21 1.385(5) . ?

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 O2 C8 115.2(2) . . ?
C10 O5 C11 117.06(18) . . ?
C18 O6 C23 118.4(3) . . ?
C1 N1 C13 123.68(18) . . ?
C22 N2 C21 109.3(2) . . ?
N1 C1 C2 121.68(19) . . ?
N1 C1 C6 120.7(2) . . ?
C6 C1 C2 117.7(2) . . ?
C1 C2 C7 120.0(2) . . ?
C3 C2 C1 119.7(2) . . ?
C3 C2 C7 120.3(2) . . ?
C4 C3 C2 121.9(2) . . ?
O3 C4 C3 118.0(2) . . ?
O3 C4 C5 122.9(2) . . ?
C3 C4 C5 119.1(2) . . ?
C4 C5 C6 119.71(19) . . ?
C4 C5 C10 119.77(19) . . ?
C6 C5 C10 120.51(19) . . ?
C5 C6 C1 121.9(2) . . ?
O1 C7 O2 121.2(2) . . ?
O1 C7 C2 124.8(2) . . ?
O2 C7 C2 113.9(2) . . ?
C9 C8 O2 110.7(3) . . ?
O4 C10 O5 122.6(2) . . ?
O4 C10 C5 123.8(2) . . ?
O5 C10 C5 113.64(18) . . ?
O5 C11 C12 107.3(2) . . ?
N1 C13 C14 110.13(19) . . ?
C15 C14 C13 111.92(19) . . ?
C16 C15 C14 126.4(2) . . ?
C22 C15 C14 127.0(3) . . ?
C22 C15 C16 106.5(2) . . ?
C17 C16 C15 133.7(2) . . ?
C21 C16 C15 107.0(2) . . ?
C21 C16 C17 119.3(3) . . ?
C18 C17 C16 118.6(3) . . ?
O6 C18 C17 125.1(3) . . ?
O6 C18 C19 114.5(3) . . ?
C17 C18 C19 120.3(3) . . ?
C20 C19 C18 121.8(3) . . ?
C19 C20 C21 118.5(3) . . ?
N2 C21 C16 107.3(3) . . ?
N2 C21 C20 131.2(3) . . ?
C20 C21 C16 121.5(3) . . ?
N2 C22 C15 109.9(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.713
_oxdiff_exptl_absorpt_empirical_full_min 0.792
