# 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_241213ak2_auto
_database_code_depnum_ccdc_archive 'CCDC 2412389'
loop_
_audit_author_name
_audit_author_address
'Kazuma Kurokawa'
;Kyoto University
Japan
;
_audit_update_record             
;
2024-12-23 deposited with the CCDC.	2025-02-11 downloaded from the CCDC.
;
_audit_creation_date             2024-12-13
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H26 O5'
_chemical_formula_sum            'C21 H26 O5'
_chemical_formula_weight         358.42
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21H26O5
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'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.52413(13)
_cell_length_b                   15.2460(4)
_cell_length_c                   22.0591(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1857.83(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10336
_cell_measurement_temperature    93
_cell_measurement_theta_max      72.0060
_cell_measurement_theta_min      3.4990
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.867
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63370
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            16572
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.318
_diffrn_reflns_theta_min         3.524
_diffrn_ambient_temperature      93
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -136.00  42.00   0.50    0.50    --  -46.90  11.00  -3.00  356
  2  ω   -187.00  -8.00   0.50    0.96    --  -97.40  11.00  -3.00  358
  3  ω    -84.00 -26.00   0.50    0.50    --    5.00  50.00 120.00  116
  4  ω    -84.00 -38.00   0.50    0.50    --    5.00  60.00  60.00   92
  5  ω    -84.00 -38.00   0.50    0.50    --    5.00  60.00  30.00   92
  6  ω     14.00  42.00   0.50    0.50    --  -46.90  46.00 142.68   56
  7  ω   -187.00 -14.00   0.50    0.96    --  -97.40  46.00  18.66  346
  8  ω   -187.00 -36.00   0.50    0.96    --  -97.40  58.00 113.93  302
  9  ω   -187.00 -35.00   0.50    0.96    --  -97.40  57.00 140.28  304
 10  ω   -187.00 -36.00   0.50    0.96    --  -97.40  58.00 177.32  302
 11  ω   -187.00  -8.00   0.50    0.96    --  -97.40  40.00  60.00  358
 12  ω   -186.00 -50.00   0.50    0.96    --  -97.40  60.00  90.33  272
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0034559000
_diffrn_orient_matrix_UB_12      -0.0851519000
_diffrn_orient_matrix_UB_13      0.0376748000
_diffrn_orient_matrix_UB_21      0.0548551000
_diffrn_orient_matrix_UB_22      -0.0530632000
_diffrn_orient_matrix_UB_23      -0.0577493000
_diffrn_orient_matrix_UB_31      0.2735087000
_diffrn_orient_matrix_UB_32      0.0117129000
_diffrn_orient_matrix_UB_33      0.0110882000
_diffrn_radiation_collimation    0.3
_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_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.705
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                3393
_reflns_number_total             3606
_reflns_odcompleteness_completeness 99.60
_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 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 1359 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(12)
_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     238
_refine_ls_number_reflns         3606
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0361
_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)+(0.0570P)²+0.2480P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.0983
_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 Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C22(H22A,H22B), C25(H25A,H25B), C23(H23A,H23B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C10(H10), C11(H11), C14(H14)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C16(H16A,H16B,H16C), C26(H26A,H26B,H26C)
;
_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
O17 O 0.8543(3) 0.63434(10) 0.34100(7) 0.0228(3) Uani 1 1 d . . . . .
O8 O 0.7679(3) 0.38508(10) 0.30104(7) 0.0247(3) Uani 1 1 d . . . . .
O19 O 0.7408(3) 0.71462(11) 0.26049(8) 0.0317(4) Uani 1 1 d . . . . .
O21 O 0.8837(3) 0.46594(11) 0.22426(7) 0.0295(4) Uani 1 1 d . . . . .
O15 O 0.2568(3) 0.65888(10) 0.61373(7) 0.0304(4) Uani 1 1 d . . . . .
C18 C 0.8917(4) 0.69758(14) 0.29762(10) 0.0240(5) Uani 1 1 d . . . . .
C12 C 0.2956(4) 0.63337(15) 0.55523(10) 0.0253(5) Uani 1 1 d . . . . .
C7 C 0.7475(4) 0.45758(14) 0.26662(9) 0.0229(4) Uani 1 1 d . . . . .
C5 C 0.6475(4) 0.58424(14) 0.33522(9) 0.0219(4) Uani 1 1 d . . . . .
C1 C 0.6145(4) 0.37005(14) 0.35414(9) 0.0234(4) Uani 1 1 d . . . . .
H1 H 0.684855 0.401576 0.389772 0.028 Uiso 1 1 calc R U . . .
C3 C 0.3587(4) 0.50023(14) 0.32855(10) 0.0241(4) Uani 1 1 d . . . . .
H3 H 0.196391 0.521052 0.314567 0.029 Uiso 1 1 calc R U . . .
C9 C 0.4102(4) 0.58751(14) 0.43604(10) 0.0229(4) Uani 1 1 d . . . . .
C4 C 0.4736(4) 0.56270(14) 0.37438(10) 0.0228(4) Uani 1 1 d . . . . .
C13 C 0.1492(4) 0.57528(15) 0.52380(10) 0.0265(5) Uani 1 1 d . . . . .
H13 H 0.010614 0.550593 0.542725 0.032 Uiso 1 1 calc R U . . .
C10 C 0.5535(4) 0.64717(15) 0.46826(10) 0.0253(5) Uani 1 1 d . . . . .
H10 H 0.691747 0.672209 0.449385 0.030 Uiso 1 1 calc R U . . .
C6 C 0.5656(4) 0.52676(14) 0.28384(10) 0.0231(5) Uani 1 1 d . . . . .
H6 H 0.505577 0.560980 0.248209 0.028 Uiso 1 1 calc R U . . .
C11 C 0.4966(4) 0.67007(15) 0.52701(10) 0.0275(5) Uani 1 1 d . . . . .
H11 H 0.594827 0.710967 0.548243 0.033 Uiso 1 1 calc R U . . .
C14 C 0.2066(4) 0.55341(15) 0.46448(11) 0.0269(5) Uani 1 1 d . . . . .
H14 H 0.104482 0.514261 0.442845 0.032 Uiso 1 1 calc R U . . .
C2 C 0.3597(4) 0.40295(14) 0.34314(10) 0.0253(5) Uani 1 1 d . . . . .
H2A H 0.259917 0.392220 0.379685 0.030 Uiso 1 1 calc R U . . .
H2B H 0.286783 0.370068 0.309014 0.030 Uiso 1 1 calc R U . . .
C22 C 0.6234(4) 0.27201(15) 0.36575(11) 0.0263(5) Uani 1 1 d . . . . .
H22A H 0.558805 0.241373 0.329632 0.032 Uiso 1 1 calc R U . . .
H22B H 0.514946 0.258344 0.400216 0.032 Uiso 1 1 calc R U . . .
C25 C 1.1103(5) 0.09722(16) 0.40853(12) 0.0321(5) Uani 1 1 d . . . . .
H25A H 1.101445 0.032512 0.405504 0.039 Uiso 1 1 calc R U . . .
H25B H 1.239723 0.117442 0.380797 0.039 Uiso 1 1 calc R U . . .
C20 C 1.1343(4) 0.73727(16) 0.30410(12) 0.0294(5) Uani 1 1 d . . . . .
H20A H 1.193441 0.728035 0.345495 0.044 Uiso 1 1 calc R U . . .
H20B H 1.124473 0.800325 0.295810 0.044 Uiso 1 1 calc R U . . .
H20C H 1.246045 0.709798 0.275276 0.044 Uiso 1 1 calc R U . . .
C23 C 0.8738(4) 0.23546(15) 0.37971(11) 0.0281(5) Uani 1 1 d . . . . .
H23A H 0.936208 0.263124 0.417183 0.034 Uiso 1 1 calc R U . . .
H23B H 0.985389 0.250611 0.346185 0.034 Uiso 1 1 calc R U . . .
C24 C 0.8698(5) 0.13608(15) 0.38790(12) 0.0315(5) Uani 1 1 d . . . . .
H24A H 0.743879 0.120961 0.418085 0.038 Uiso 1 1 calc R U . . .
H24B H 0.823217 0.108607 0.348939 0.038 Uiso 1 1 calc R U . . .
C16 C 0.0844(5) 0.61025(16) 0.64785(11) 0.0335(5) Uani 1 1 d . . . . .
H16A H -0.075628 0.616056 0.629070 0.050 Uiso 1 1 calc R U . . .
H16B H 0.078441 0.632914 0.689393 0.050 Uiso 1 1 calc R U . . .
H16C H 0.131443 0.548288 0.648575 0.050 Uiso 1 1 calc R U . . .
C26 C 1.1776(5) 0.12202(19) 0.47287(12) 0.0401(6) Uani 1 1 d . . . . .
H26A H 1.193961 0.185885 0.475842 0.060 Uiso 1 1 calc R U . . .
H26B H 1.331592 0.094222 0.483699 0.060 Uiso 1 1 calc R U . . .
H26C H 1.050761 0.102011 0.500677 0.060 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
O17 C18 1.374(3) . ?
O17 C5 1.380(3) . ?
O8 C7 1.346(3) . ?
O8 C1 1.464(3) . ?
O19 C18 1.198(3) . ?
O21 C7 1.206(3) . ?
O15 C12 1.365(3) . ?
O15 C16 1.422(3) . ?
C18 C20 1.477(3) . ?
C12 C13 1.385(3) . ?
C12 C11 1.391(3) . ?
C7 C6 1.505(3) . ?
C5 C4 1.333(3) . ?
C5 C6 1.502(3) . ?
C1 C2 1.514(3) . ?
C1 C22 1.517(3) . ?
C3 C4 1.527(3) . ?
C3 C6 1.563(3) . ?
C3 C2 1.518(3) . ?
C9 C4 1.455(3) . ?
C9 C10 1.400(3) . ?
C9 C14 1.389(3) . ?
C13 C14 1.387(3) . ?
C10 C11 1.379(3) . ?
C22 C23 1.523(3) . ?
C25 C24 1.524(3) . ?
C25 C26 1.515(4) . ?
C23 C24 1.526(3) . ?

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
C18 O17 C5 116.64(17) . . ?
C7 O8 C1 122.10(17) . . ?
C12 O15 C16 117.18(19) . . ?
O17 C18 C20 110.89(19) . . ?
O19 C18 O17 121.6(2) . . ?
O19 C18 C20 127.5(2) . . ?
O15 C12 C13 124.3(2) . . ?
O15 C12 C11 115.7(2) . . ?
C13 C12 C11 120.0(2) . . ?
O8 C7 C6 119.28(19) . . ?
O21 C7 O8 118.1(2) . . ?
O21 C7 C6 122.5(2) . . ?
O17 C5 C6 129.93(18) . . ?
C4 C5 O17 132.3(2) . . ?
C4 C5 C6 97.36(18) . . ?
O8 C1 C2 111.00(17) . . ?
O8 C1 C22 105.69(17) . . ?
C2 C1 C22 112.56(18) . . ?
C4 C3 C6 87.27(16) . . ?
C2 C3 C4 117.89(19) . . ?
C2 C3 C6 112.60(18) . . ?
C10 C9 C4 120.5(2) . . ?
C14 C9 C4 121.3(2) . . ?
C14 C9 C10 118.2(2) . . ?
C5 C4 C3 91.39(18) . . ?
C5 C4 C9 135.7(2) . . ?
C9 C4 C3 132.9(2) . . ?
C12 C13 C14 119.5(2) . . ?
C11 C10 C9 120.9(2) . . ?
C7 C6 C3 117.78(18) . . ?
C5 C6 C7 113.46(18) . . ?
C5 C6 C3 83.98(16) . . ?
C10 C11 C12 120.1(2) . . ?
C13 C14 C9 121.4(2) . . ?
C1 C2 C3 111.16(18) . . ?
C1 C22 C23 115.09(18) . . ?
C26 C25 C24 113.4(2) . . ?
C22 C23 C24 111.96(19) . . ?
C25 C24 C23 114.1(2) . . ?

_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 1.865
_oxdiff_exptl_absorpt_empirical_full_min 0.445
